Supporting Information Electrochemical sensing of ecstasy ...€¦ · 14/46 4. Figure S2....
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1/46 Supporting Information Electrochemical sensing of ecstasy with electropolymerized molecularly imprinted poly(o-phenylenediamine) polymer on the surface of disposable screen-printed carbon electrodes Rosa A. S. Couto, Séfora S. Costa, Bassim Mounssef Jr., João G. Pacheco, Eduarda Fernandes, Félix Carvalho, Cecília M. P. Rodrigues, Cristina Delerue-Matos, Ataualpa A. C. Braga, Luís Moreira Gonçalves, and M. Beatriz Quinaz Index 1. NMR spectra of MDMA hydrochloride ...................................................................................... 2 2. MS spectra of MDMA hydrochloride ......................................................................................... 6 3. Figure S1. Square wave voltammograms of the SPCE-MIP before (black) and after (red) the removal of MDMA template, SWV was performed in the potential range of 0.0 to +1.6 V, at a frequency of 25 Hz. ....................................................................................................................... 13 4. Figure S2. Electropolymerization of o-PD to poly(o-PD) on the SPCE´s surface by CV, after optimization, at a scanning rate of 100 mV s -1 , at pH = 5.0, with 0.50 mmol L -1 of o-PD and 2.0 mmol L -1 MDMA. ........................................................................................................................... 14 5. Cartesian coordinates and enthalpies for the most stable conformers of interacting MDMA and tetramer 1 (ramified) - the most stable at top of the list:................................................................. 15 6. Cartesian coordinates and enthalpies for the most stable conformers of interacting MDMA and tetramer 2 (linear) - the most stable at top of the list: .................................................................... 30 7. Figure S3. Square wave voltammograms after 10 minutes of incubation with 50 μL of 100 μmol L -1 epinephrine, norepinephrine, dopamine, tyramine, amphetamine, methamphetamine, caffeine and MDMA. Polymerization conditions: 0.50 mmol L -1 o-PD, 2.0 mmol L -1 MDMA and 5 scanning cycles. SWV was performed in the potential range of 0.0 to +1.6 V, at a frequency of 25 Hz. The SWVs had their baseline corrected by the ‘moving average’ feature present in the GPES software. ....................................................................................................................................... 45 8. Figure S4. Calibration curves for urine (1:10) and serum (1:20). ............................................ 46
Transcript of Supporting Information Electrochemical sensing of ecstasy ...€¦ · 14/46 4. Figure S2....
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Supporting Information
Electrochemical sensing of ecstasy with electropolymerized molecularly
imprinted poly(o-phenylenediamine) polymer on the surface of disposable
screen-printed carbon electrodes
Rosa A. S. Couto, Séfora S. Costa, Bassim Mounssef Jr., João G. Pacheco,
Eduarda Fernandes, Félix Carvalho, Cecília M. P. Rodrigues, Cristina Delerue-Matos,
Ataualpa A. C. Braga, Luís Moreira Gonçalves, and M. Beatriz Quinaz
Index
1. NMR spectra of MDMA hydrochloride ...................................................................................... 2
2. MS spectra of MDMA hydrochloride ......................................................................................... 6
3. Figure S1. Square wave voltammograms of the SPCE-MIP before (black) and after (red) the removal of MDMA template, SWV was performed in the potential range of 0.0 to +1.6 V, at a frequency of 25 Hz. ....................................................................................................................... 13
4. Figure S2. Electropolymerization of o-PD to poly(o-PD) on the SPCE´s surface by CV, after optimization, at a scanning rate of 100 mV s-1, at pH = 5.0, with 0.50 mmol L-1 of o-PD and 2.0 mmol L-1 MDMA. ........................................................................................................................... 14
5. Cartesian coordinates and enthalpies for the most stable conformers of interacting MDMA and tetramer 1 (ramified) - the most stable at top of the list:................................................................. 15
6. Cartesian coordinates and enthalpies for the most stable conformers of interacting MDMA and tetramer 2 (linear) - the most stable at top of the list: .................................................................... 30
7. Figure S3. Square wave voltammograms after 10 minutes of incubation with 50 μL of 100 μmol L-1 epinephrine, norepinephrine, dopamine, tyramine, amphetamine, methamphetamine, caffeine and MDMA. Polymerization conditions: 0.50 mmol L-1 o-PD, 2.0 mmol L-1 MDMA and 5 scanning cycles. SWV was performed in the potential range of 0.0 to +1.6 V, at a frequency of 25 Hz. The SWVs had their baseline corrected by the ‘moving average’ feature present in the GPES software. ....................................................................................................................................... 45
8. Figure S4. Calibration curves for urine (1:10) and serum (1:20). ............................................ 46
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1. NMR spectra of MDMA hydrochloride
13C, 75 MHz, ca. 200 a 0 ppm
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1H, 300 MHz, ca. 10 a 5 ppm
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1H, 300 MHz, ca. 6.9 a 6.5 ppm
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300 MHz, ca. 3.5 a 1.1 ppm
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2. MS spectra of MDMA hydrochloride
ca. 100 a 1500 m/z
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ca. 100 a 225 m/z
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ca. 400 a 450 m/z
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ca. 630 a 870 m/z
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ca. 900 a 1500 m/z
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ca. 930 a 1130 m/z
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ca. 1150 a 1500 m/z
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3. Figure S1. Square wave voltammograms of the SPCE-MIP before (black) and after (red)
the removal of MDMA template, SWV was performed in the potential range of 0.0 to +1.6 V,
at a frequency of 25 Hz.
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4. Figure S2. Electropolymerization of o-PD to poly(o-PD) on the SPCE´s surface by CV, after
optimization, at a scanning rate of 100 mV s-1, at pH = 5.0, with 0.50 mmol L-1 of o-PD and
2.0 mmol L-1 MDMA.
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5. Cartesian coordinates and enthalpies for the most stable conformers of interacting MDMA
and tetramer 1 (ramified) - the most stable at top of the list:
Conformer 1 Enthalpy: -1253798.96 C -6.059565 -0.310435 0.922049 C -4.668119 -0.141448 0.863439 C -3.829161 -1.183636 1.340278 C -4.420120 -2.353776 1.852064 C -5.803441 -2.503014 1.912395 H -7.703942 -1.571621 1.482745 H -6.698900 0.483928 0.545872 H -3.766400 -3.130489 2.237211 H -6.233776 -3.408340 2.328088 C -1.992050 -2.924732 -0.033000 C -1.068378 -3.746633 -0.566646 C 0.352058 -3.663109 -0.218583 C 0.755528 -2.587321 0.740360 C -0.200779 -1.749881 1.247558 C -1.606829 -1.863104 0.907303 H -3.031189 -2.992693 -0.330862 H -1.338439 -4.500089 -1.299786 H 0.057615 -1.005658 1.990478 C 4.138890 -1.880580 1.985751 C 4.947551 -0.878753 2.379840 C 4.581565 0.529784 2.194640 C 3.269877 0.812262 1.531128 C 2.491578 -0.232144 1.105329 C 2.832618 -1.606305 1.378961 H 4.401713 -2.922972 2.132513 H 5.905748 -1.070524 2.851727 H 1.599550 -0.029650 0.530434 C 1.694854 3.997986 0.695070 C 0.500126 4.586996 0.506086 C -0.749323 3.916934 0.884450 C -0.628946 2.594599 1.576099 C 0.611324 2.029997 1.758675 C 1.802735 2.646791 1.264450 H 2.621544 4.474773 0.393677 H 0.421473 5.570162 0.051223 H 0.683937 1.086593 2.281987 N -2.438156 -0.982751 1.409372 N 2.077002 -2.647379 1.126383 N 3.018501 2.137489 1.279037 N -1.777780 2.019976 1.991506 N -1.935004 4.363094 0.655511 N 5.394043 1.449213 2.586429 N 1.182400 -4.475557 -0.774178 N -4.111288 1.035359 0.364115 H -3.200141 0.934569 -0.060076 H -4.732258 1.602450 -0.197661 H 2.126131 -4.255549 -0.434100 H 4.976287 2.360974 2.359453 H -1.823573 1.006870 2.100666 H -2.639591 2.440543 1.663845
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H -1.900239 5.267086 0.176909 C 2.226244 -1.017419 -2.136016 C 0.862877 -0.818826 -2.069781 C 0.399712 0.510601 -1.939795 C 1.319214 1.565225 -1.924789 C 2.707604 1.352362 -2.006197 C 3.131389 0.042414 -2.097406 H 0.171866 -1.652145 -2.087814 H 0.954597 2.581062 -1.809380 H 3.412314 2.173875 -1.958989 O 2.913685 -2.207120 -2.228604 O 4.417611 -0.444834 -2.163854 C 4.288342 -1.864608 -1.984382 C -1.079792 0.790979 -1.813799 H -1.574860 -0.063346 -1.335188 H -1.212092 1.653489 -1.152184 C -1.807055 1.077610 -3.158324 H -1.251303 1.875346 -3.670864 H 4.926080 -2.383878 -2.701878 H 4.549761 -2.126672 -0.949828 C -1.828522 -0.162350 -4.055277 H -2.375775 -0.977843 -3.565796 H -0.816721 -0.519098 -4.264147 H -2.325698 0.062033 -5.002697 N -3.180594 1.564605 -2.990999 C -3.318157 2.892465 -2.396744 H -4.378932 3.161854 -2.361137 H -2.908922 3.015851 -1.379987 H -2.813726 3.625435 -3.036285 H -3.719334 0.882856 -2.459858 Conformer 2 Enthalpy: -1253788.42 C -6.899895 2.554461 2.357174 C -6.638936 1.178948 2.225401 C -5.996108 0.709423 1.037291 C -5.710464 1.631912 0.008348 C -6.001248 2.984425 0.145895 H -6.806891 4.499080 1.458860 H -7.368755 2.914705 3.268903 H -5.301288 1.257632 -0.924093 H -5.790309 3.671510 -0.667098 C -4.853353 -2.681242 0.190917 C -3.889950 -3.369684 -0.453728 C -2.698499 -2.706849 -0.980181 C -2.555231 -1.249899 -0.685083 C -3.561011 -0.566908 -0.063944 C -4.781023 -1.229287 0.366968 H -5.745960 -3.168988 0.569218 H -3.965950 -4.439545 -0.619565 H -3.412339 0.474855 0.194082 C -2.033963 1.126797 -2.355642 C -1.660919 2.203336 -3.072361 C -0.267540 2.660626 -3.132278 C 0.735956 1.896150 -2.330017 C 0.333870 0.806165 -1.612740
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C -1.042361 0.358107 -1.590167 H -3.061803 0.784302 -2.358328 H -2.375509 2.765355 -3.665383 H 1.050688 0.223586 -1.045297 C 4.316359 2.534235 -1.945180 C 5.312193 2.591186 -1.044867 C 5.039441 2.576726 0.396344 C 3.603193 2.560555 0.815528 C 2.612577 2.432546 -0.124798 C 2.912928 2.394747 -1.527474 H 4.507107 2.543425 -3.013079 H 6.351797 2.649146 -1.354239 H 1.577075 2.384428 0.191165 N -5.813076 -0.665498 0.941201 N -1.297874 -0.738090 -0.929338 N 2.047325 2.275388 -2.506007 N 3.373532 2.711429 2.143139 N 5.935420 2.583614 1.320087 N 0.027513 3.678369 -3.864166 N -1.832796 -3.376983 -1.667886 N -7.007155 0.280987 3.204547 H -6.563987 -0.624905 3.162140 H -7.140923 0.642187 4.137642 H -1.083941 -2.740091 -1.959587 H 1.041805 3.835551 -3.806499 H 2.455898 2.477294 2.493401 H 4.146899 2.484198 2.755931 H 6.874710 2.589945 0.913886 C 4.428987 -1.025498 1.428388 C 3.822025 -1.698845 0.386801 C 2.410633 -1.783129 0.392364 C 1.685561 -1.169104 1.423160 C 2.316172 -0.491798 2.483304 C 3.695699 -0.449367 2.463276 H 4.408544 -2.147843 -0.407973 H 0.601735 -1.224864 1.402384 H 1.747118 -0.024696 3.279362 O 5.769270 -0.779556 1.618532 O 4.551123 0.177377 3.344092 C 5.872068 -0.229703 2.942489 C 1.700554 -2.587403 -0.670874 H 0.666667 -2.239470 -0.755952 H 2.183335 -2.411206 -1.638336 C 1.681412 -4.121078 -0.392323 H 2.727861 -4.453200 -0.313738 H 6.520916 0.645507 2.920242 H 6.238661 -1.002886 3.631174 C 0.963949 -4.443676 0.921364 H 0.965280 -5.523086 1.097290 H 1.438569 -3.945674 1.769831 H -0.078917 -4.106131 0.875336 N 1.060926 -4.918139 -1.456674 C 1.663384 -4.796055 -2.780177 H 1.602457 -3.795388 -3.239792 H 1.179315 -5.501436 -3.463533 H 2.725058 -5.064254 -2.722570 H 0.066957 -4.695456 -1.506819
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Conformer 3 Enthalpy: -1253795.13 C -0.013216 -5.620274 0.415907 C -0.367019 -4.261519 0.304932 C -0.239421 -3.436679 1.462909 C 0.214101 -4.010485 2.668683 C 0.543307 -5.358033 2.756975 H 0.684630 -7.217213 1.664983 H -0.095808 -6.250530 -0.465848 H 0.251668 -3.381227 3.552495 H 0.866960 -5.778607 3.703420 C 1.371471 -1.144908 2.345998 C 2.009122 -0.016878 2.717198 C 1.354838 1.293418 2.736777 C -0.080905 1.342280 2.316672 C -0.698898 0.179755 1.939754 C -0.028151 -1.106159 1.904128 H 1.902663 -2.087772 2.315049 H 3.055652 -0.031803 3.005433 H -1.753783 0.168528 1.702549 C -2.324884 4.244455 2.381455 C -3.478316 4.722775 1.878820 C -4.135585 4.096487 0.728632 C -3.453044 2.912822 0.110449 C -2.249900 2.490274 0.612987 C -1.691040 3.046086 1.825026 H -1.845851 4.691508 3.246175 H -3.973402 5.588245 2.307102 H -1.709497 1.701493 0.107301 C -4.691993 0.815205 -2.623580 C -4.759144 -0.450744 -3.072442 C -4.289943 -1.578439 -2.257288 C -3.801195 -1.260673 -0.876575 C -3.796535 0.043659 -0.436031 C -4.151108 1.133462 -1.292737 H -5.010993 1.654957 -3.231850 H -5.143485 -0.677568 -4.062802 H -3.484767 0.249606 0.578318 N -0.699051 -2.115780 1.403201 N -0.677127 2.569611 2.506558 N -4.071416 2.418210 -1.012305 N -3.378999 -2.300794 -0.125748 N -4.244910 -2.805638 -2.639380 N -5.244309 4.583873 0.290340 N 2.034113 2.328578 3.094280 N -0.845630 -3.754327 -0.890999 H -0.634831 -2.778224 -1.129248 H -0.712664 -4.366668 -1.685455 H 1.413305 3.146782 3.054375 H -5.540734 4.024415 -0.519731 H -2.676224 -2.113337 0.591539 H -3.192316 -3.155115 -0.640671 H -4.600498 -2.902198 -3.594570 C 5.478750 1.093946 -0.589470 C 4.160562 0.776067 -0.331045 C 3.217340 1.010757 -1.356249
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C 3.640568 1.544639 -2.579353 C 4.988125 1.861023 -2.833065 C 5.886751 1.623606 -1.811509 H 3.859617 0.359067 0.623073 H 2.904325 1.726444 -3.357252 H 5.308584 2.274287 -3.782724 O 6.569593 0.934090 0.233653 O 7.250125 1.816101 -1.802675 C 7.659982 1.579699 -0.445708 C 1.765168 0.648495 -1.147626 H 1.542455 0.597960 -0.076667 H 1.129401 1.436975 -1.565644 C 1.352707 -0.702605 -1.789404 H 1.610041 -0.660761 -2.855434 H 8.533318 0.923524 -0.437728 H 7.878924 2.538588 0.043526 C 2.085022 -1.894424 -1.170527 H 1.809206 -2.018852 -0.120289 H 3.168404 -1.756765 -1.219208 H 1.822334 -2.815939 -1.696241 N -0.109835 -0.911569 -1.716476 C -0.850821 -0.203277 -2.764137 H -0.619422 -0.650069 -3.736150 H -1.920469 -0.308407 -2.589271 H -0.627261 0.873334 -2.825449 H -0.437512 -0.598865 -0.804033 Conformer 4 Enthalpy: -1253786.32 C -3.845067 5.250405 -1.487981 C -3.329230 3.959065 -1.690790 C -2.785677 3.249458 -0.576538 C -2.840681 3.841461 0.702288 C -3.371688 5.113023 0.886532 H -4.277293 6.815119 -0.087217 H -4.242157 5.797460 -2.338624 H -2.509310 3.263058 1.558043 H -3.420963 5.542052 1.881938 C -0.371967 1.982944 0.619232 C 0.567789 1.254407 1.254728 C 0.621457 -0.206967 1.153213 C -0.380320 -0.864395 0.265692 C -1.274264 -0.090778 -0.420251 C -1.388940 1.339836 -0.219231 H -0.363596 3.064323 0.684821 H 1.351371 1.724134 1.841764 H -1.961164 -0.540460 -1.127576 C -0.933222 -4.436641 -0.356247 C -1.919682 -5.329925 -0.558788 C -3.329761 -4.993588 -0.333176 C -3.633762 -3.609772 0.155198 C -2.603205 -2.737171 0.378211 C -1.230445 -3.063002 0.057806 H 0.108932 -4.680993 -0.533750 H -1.713879 -6.340213 -0.897499
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H -2.811325 -1.766760 0.808674 C -6.908470 -2.124468 0.841070 C -7.627516 -0.990915 0.763648 C -7.105306 0.199923 0.083818 C -5.760305 0.074667 -0.564066 C -5.057467 -1.105543 -0.471547 C -5.557990 -2.225641 0.263792 H -7.283382 -3.004578 1.352919 H -8.615494 -0.918455 1.209223 H -4.103680 -1.183721 -0.974592 N -2.383685 1.939941 -0.824777 N -0.221154 -2.228663 0.105831 N -4.954738 -3.381814 0.459438 N -5.314863 1.153532 -1.235910 N -7.702391 1.336189 -0.001027 N -4.232802 -5.887103 -0.545208 N 1.528984 -0.855198 1.804090 N -3.372621 3.352064 -2.930705 H -3.503106 3.955912 -3.729638 H -2.713908 2.602560 -3.083613 H 1.442400 -1.855594 1.592695 H -5.147309 -5.475107 -0.318969 H -5.851316 2.005102 -1.137805 H -4.323703 1.244961 -1.447731 H -8.612168 1.306621 0.467330 C 7.691391 -0.696642 -1.367856 C 6.579375 -0.768281 -0.552615 C 6.673976 -0.201534 0.738412 C 7.873440 0.399209 1.142468 C 9.001804 0.464108 0.304115 C 8.876819 -0.094218 -0.952787 H 5.665161 -1.242642 -0.892638 H 7.935556 0.830704 2.137585 H 9.928227 0.924738 0.628278 O 7.849649 -1.200537 -2.639497 O 9.824509 -0.200043 -1.947658 C 9.110805 -0.683917 -3.096478 C 5.476696 -0.195372 1.660745 H 4.760857 -0.970824 1.361787 H 5.807094 -0.440664 2.675768 C 4.719797 1.165057 1.701482 H 5.457695 1.946294 1.936082 H 8.933838 0.145895 -3.794921 H 9.682414 -1.484799 -3.570330 C 4.084896 1.484952 0.344827 H 3.590375 2.459859 0.374908 H 3.331608 0.730404 0.092599 H 4.834398 1.494104 -0.451343 N 3.685459 1.219405 2.740724 C 4.180973 1.237086 4.113116 H 3.330883 1.269974 4.802046 H 4.779302 2.141248 4.278849 H 4.806273 0.374750 4.401459 H 3.045448 0.433164 2.605934
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Conformer 5 Enthalpy: -1253795.01 C -5.336319 -3.327066 -0.487126 C -4.258067 -2.426374 -0.407702 C -3.601252 -2.270001 0.846998 C -4.039633 -3.026905 1.952118 C -5.111684 -3.907334 1.851995 H -6.603290 -4.731958 0.524461 H -5.836467 -3.455081 -1.443826 H -3.551093 -2.866420 2.908386 H -5.445696 -4.459082 2.724638 C -0.927408 -2.814897 1.865799 C 0.330163 -2.949684 2.330862 C 1.179094 -1.800939 2.651644 C 0.589592 -0.438829 2.455446 C -0.677426 -0.336097 1.945022 C -1.489450 -1.486359 1.596025 H -1.514478 -3.686203 1.603116 H 0.778886 -3.928725 2.465467 H -1.156653 0.628768 1.853378 C 2.070377 2.783484 3.402408 C 2.007430 4.106483 3.162393 C 1.288654 4.647614 2.005331 C 0.648790 3.661656 1.072644 C 0.780507 2.320137 1.323043 C 1.385363 1.820883 2.535518 H 2.584183 2.380510 4.268796 H 2.481376 4.829486 3.818293 H 0.408008 1.608718 0.601482 C -1.399464 4.424838 -1.866885 C -2.473015 4.041456 -2.580192 C -3.323962 2.928895 -2.143069 C -2.959934 2.262595 -0.850729 C -1.888003 2.726775 -0.119712 C -1.029424 3.759304 -0.607385 H -0.754885 5.233486 -2.194898 H -2.737819 4.535220 -3.510779 H -1.683866 2.277104 0.840253 N -2.634802 -1.264450 0.996971 N 1.365430 0.580378 2.961724 N 0.063724 4.224871 -0.033701 N -3.723635 1.222682 -0.465863 N -4.336840 2.465889 -2.786502 N 1.246385 5.922333 1.827406 N 2.386520 -2.004257 3.057471 N -3.854640 -1.694130 -1.514586 H -2.848777 -1.532201 -1.631503 H -4.276943 -1.998321 -2.382802 H 2.820736 -1.090191 3.237647 H 0.715626 6.105204 0.965775 H -3.357321 0.539611 0.200983 H -4.356890 0.839763 -1.157237 H -4.491541 2.992247 -3.650704 C 4.783524 -1.752241 -0.766521 C 3.467158 -1.408612 -0.531448 C 2.774780 -0.735173 -1.562924 C 3.430136 -0.446812 -2.766402
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C 4.770922 -0.806641 -2.995285 C 5.423730 -1.460665 -1.968715 H 2.990876 -1.647257 0.413040 H 2.888196 0.078108 -3.548066 H 5.271708 -0.579307 -3.929541 O 5.648068 -2.424841 0.066855 O 6.714179 -1.940373 -1.936356 C 6.931226 -2.353194 -0.577110 C 1.323996 -0.352559 -1.381705 H 1.069723 -0.370443 -0.316341 H 1.168700 0.675029 -1.731682 C 0.318759 -1.274041 -2.119269 H 0.594849 -1.294911 -3.180789 H 7.399875 -3.339732 -0.566040 H 7.556585 -1.609812 -0.063909 C 0.350455 -2.707345 -1.589265 H 0.061523 -2.739453 -0.535754 H 1.354739 -3.132973 -1.672334 H -0.346231 -3.333973 -2.153133 N -1.056090 -0.737480 -2.048114 C -1.360100 0.272704 -3.064433 H -1.193272 -0.158164 -4.056327 H -2.414777 0.544051 -2.995948 H -0.761035 1.193707 -2.989812 H -1.206219 -0.337676 -1.122480 Conformer 6 Enthalpy: -1253790.04 C -4.204446 -4.606961 2.575878 C -4.448124 -3.353732 1.989213 C -3.563328 -2.880174 0.971691 C -2.448394 -3.670334 0.616929 C -2.213982 -4.900170 1.220854 H -2.928649 -6.328045 2.675648 H -4.883826 -4.969683 3.342352 H -1.732711 -3.278494 -0.097281 H -1.336392 -5.478382 0.950607 C -3.260539 -1.985442 -1.854557 C -2.929393 -1.426820 -3.036501 C -2.819234 0.023504 -3.216998 C -3.135216 0.871946 -2.033410 C -3.530323 0.286399 -0.866526 C -3.540590 -1.151542 -0.680536 H -3.363434 -3.060004 -1.761909 H -2.749451 -2.034372 -3.917911 H -3.785982 0.893000 -0.004700 C -2.895316 4.515041 -1.736527 C -2.471583 5.500303 -0.924885 C -1.642174 5.221903 0.250842 C -1.208735 3.803823 0.451244 C -1.686561 2.809047 -0.356403 C -2.587461 3.107636 -1.457617 H -3.517483 4.713271 -2.603108 H -2.730593 6.539445 -1.100525 H -1.387341 1.780288 -0.165283
23/46
C 1.518204 2.814439 0.285675 C 2.752708 2.282283 0.304538 C 3.389016 1.851069 1.555157 C 2.629678 2.093270 2.822574 C 1.383161 2.664064 2.775851 C 0.758965 3.024057 1.534789 H 1.060404 3.123530 -0.646514 H 3.317749 2.140874 -0.612405 H 0.820940 2.838204 3.687232 N -3.787039 -1.583194 0.530904 N -3.135364 2.235754 -2.263002 N -0.424319 3.581953 1.560986 N 3.263922 1.727325 3.957168 N 4.534434 1.274294 1.653602 N -1.297330 6.192103 1.025619 N -2.468733 0.491304 -4.367769 N -5.557415 -2.598272 2.319401 H -5.478121 -1.624184 2.047943 H -5.924108 -2.735188 3.251772 H -2.467814 1.517100 -4.313908 H -0.725132 5.811395 1.789540 H 4.124791 1.206872 3.865244 H 2.780032 1.719798 4.840934 H 4.971577 1.126649 0.740315 C 4.973138 -1.580750 -0.434321 C 3.706772 -1.593468 0.109320 C 2.670957 -2.182498 -0.653316 C 2.965800 -2.746281 -1.898853 C 4.268228 -2.740121 -2.436877 C 5.253411 -2.139170 -1.679720 H 3.512639 -1.146250 1.077424 H 2.163939 -3.194730 -2.477648 H 4.486043 -3.174208 -3.406113 O 6.114140 -1.008467 0.084469 O 6.582633 -1.948917 -1.986251 C 7.179576 -1.416127 -0.793031 C 1.252733 -2.090030 -0.139447 H 0.589163 -2.734793 -0.728612 H 1.212884 -2.445666 0.896139 C 0.723282 -0.626539 -0.194390 H 1.468103 0.002127 0.304661 H 7.776686 -2.195809 -0.301647 H 7.792426 -0.548422 -1.046724 C 0.575931 -0.148637 -1.640659 H 0.266075 0.898550 -1.670458 H 1.516567 -0.252428 -2.187020 H -0.182689 -0.742702 -2.163823 N -0.539229 -0.393418 0.505516 C -0.546981 -0.634353 1.944600 H -1.541894 -0.396546 2.332303 H 0.175035 0.034526 2.425462 H -0.311064 -1.667241 2.246908 H -1.277445 -0.930700 0.064617
24/46
Conformer 7 Enthalpy: -1253793.47 C -7.246625 -0.231211 0.540839 C -5.848794 -0.147538 0.428301 C -5.108105 -1.317632 0.070753 C -5.801969 -2.531238 -0.121527 C -7.185269 -2.597104 0.006313 H -8.985370 -1.482720 0.434835 H -7.807195 0.661762 0.803691 H -5.231575 -3.434524 -0.310969 H -7.697659 -3.544927 -0.123446 C -3.236813 -2.560029 -1.899320 C -2.283057 -3.172083 -2.629237 C -0.864578 -3.129773 -2.266636 C -0.501610 -2.349804 -1.044497 C -1.482810 -1.694979 -0.353360 C -2.890162 -1.803757 -0.691980 H -4.270666 -2.576150 -2.222469 H -2.526384 -3.703223 -3.544281 H -1.244626 -1.059481 0.491139 C 0.778421 -2.562292 1.627780 C 1.458833 -2.486232 2.787336 C 2.875740 -2.112326 2.843874 C 3.565573 -1.835120 1.543277 C 2.851155 -1.946523 0.380376 C 1.436440 -2.249790 0.352214 H -0.256910 -2.879641 1.614820 H 0.989665 -2.730203 3.735320 H 3.331409 -1.799025 -0.580323 C 7.049093 -0.785689 1.075176 C 7.856492 0.041807 0.388369 C 7.316652 1.049414 -0.532778 C 5.824244 1.132915 -0.648311 C 5.032289 0.258477 0.067465 C 5.585095 -0.735824 0.925107 H 7.443198 -1.533544 1.755479 H 8.936696 -0.009559 0.491947 H 3.960107 0.345163 -0.008386 N -3.727190 -1.181615 0.097465 N 0.856994 -2.246759 -0.822501 N 4.917395 -1.609840 1.652767 N 5.327817 2.083442 -1.454917 N 8.015480 1.865077 -1.240656 N 3.464697 -2.056790 3.988156 N -0.004929 -3.734754 -3.015196 N -5.171763 1.045253 0.582605 H -5.581225 1.728502 1.205537 H -4.173740 0.926207 0.716819 H 0.930904 -3.567910 -2.624999 H 4.450609 -1.813680 3.824219 H 4.320861 2.080074 -1.682702 H 5.986946 2.628957 -1.992586 H 9.016142 1.723793 -1.076827 C -2.817800 3.352093 -0.050307 C -1.802645 2.779564 -0.788155 C -0.907984 1.918535 -0.113537 C -1.074038 1.677447 1.255670
25/46
C -2.118597 2.261912 1.998128 C -2.972696 3.101732 1.312633 H -1.706681 2.968508 -1.852068 H -0.380314 1.012916 1.762187 H -2.256335 2.052442 3.052596 O -3.837857 4.159261 -0.492152 O -4.119041 3.720233 1.766751 C -4.528012 4.586768 0.693512 C 0.227401 1.283096 -0.879316 H 0.560880 0.378428 -0.361343 H -0.134292 0.963632 -1.862580 C 1.466836 2.193372 -1.068746 H 1.151817 3.119432 -1.566381 H -5.604701 4.492259 0.542363 H -4.244254 5.620982 0.929590 C 2.106678 2.557526 0.273000 H 1.400811 3.106893 0.901111 H 2.402263 1.656764 0.822232 H 2.996403 3.174202 0.121132 N 2.471122 1.559711 -1.953346 C 2.151036 1.632378 -3.385105 H 2.170412 2.678721 -3.704555 H 2.915432 1.090888 -3.948863 H 1.169110 1.213294 -3.649404 H 2.544913 0.575415 -1.695584 Conformer 8 Enthalpy: -1253794.10 C 6.706670 -0.917427 0.563019 C 5.701036 -0.503138 -0.327237 C 4.401776 -1.091750 -0.227416 C 4.151816 -2.025598 0.801412 C 5.155678 -2.405325 1.685010 H 7.228894 -2.151153 2.236530 H 7.698195 -0.481775 0.476056 H 3.143185 -2.395153 0.950312 H 4.936336 -3.106331 2.483697 C 2.243716 -2.667025 -1.573187 C 1.116610 -3.225514 -2.059843 C 0.020611 -2.429768 -2.619460 C 0.234088 -0.955411 -2.704619 C 1.412960 -0.422891 -2.261077 C 2.429734 -1.212498 -1.593114 H 3.043095 -3.287304 -1.186700 H 0.979487 -4.302132 -2.068449 H 1.612421 0.637272 -2.365988 C -2.148052 1.622302 -3.792013 C -2.607962 2.843348 -3.459416 C -2.246021 3.494991 -2.194712 C -1.332750 2.742345 -1.277061 C -0.891900 1.500610 -1.646318 C -1.222256 0.899157 -2.916481 H -2.417274 1.142330 -4.727105 H -3.275566 3.397350 -4.111469 H -0.291890 0.929779 -0.955495
26/46
C -0.086561 3.656447 2.035039 C 0.936584 3.492737 2.892622 C 2.193437 2.866327 2.469111 C 2.309282 2.488629 1.024700 C 1.241654 2.674634 0.175458 C -0.007899 3.192575 0.640919 H -1.026279 4.101044 2.345199 H 0.860186 3.806828 3.929572 H 1.355120 2.414771 -0.868229 N 3.437194 -0.554855 -1.074407 N -0.771082 -0.254719 -3.345920 N -1.122245 3.327574 -0.052723 N 3.491855 1.977451 0.632790 N 3.195341 2.605398 3.232471 N -2.729925 4.656856 -1.922578 N -1.059530 -3.022162 -3.006223 N 5.931400 0.483526 -1.263706 H 6.894059 0.685131 -1.492303 H 5.302064 0.508369 -2.052371 H -1.696584 -2.312063 -3.387793 H -2.382794 4.937802 -0.996286 H 4.158505 1.765405 1.363498 H 3.547777 1.429702 -0.222444 H 3.010496 2.905286 4.193470 C -5.014692 -0.877147 1.848101 C -3.651458 -0.666246 1.868838 C -2.895245 -1.170763 0.786058 C -3.537625 -1.856321 -0.251275 C -4.930049 -2.066045 -0.260294 C -5.643115 -1.560489 0.807966 H -3.178493 -0.127684 2.683431 H -2.943049 -2.241417 -1.074636 H -5.421518 -2.597499 -1.067368 O -5.948110 -0.505431 2.787986 O -6.994661 -1.644720 1.058109 C -7.225397 -0.800632 2.197600 C -1.398266 -0.980900 0.772497 H -1.030359 -1.110816 -0.250625 H -1.161600 0.046506 1.070954 C -0.598155 -1.954472 1.679259 H -0.964998 -1.846906 2.708948 H -7.701791 0.133952 1.871377 H -7.848099 -1.329231 2.922959 C -0.780636 -3.409468 1.242680 H -1.835826 -3.695488 1.250991 H -0.226580 -4.077676 1.907422 H -0.402966 -3.552952 0.224452 N 0.837811 -1.629113 1.699782 C 1.196738 -0.455437 2.493965 H 0.648151 0.464063 2.236715 H 1.014616 -0.663143 3.554159 H 2.263488 -0.250665 2.368970 H 1.142530 -1.481540 0.740427
27/46
Conformer 9 Enthalpy: -1253796.87 C 5.063428 -2.385178 0.412305 C 3.764631 -2.743455 0.019598 C 2.710799 -2.713569 0.984604 C 3.003535 -2.307308 2.301402 C 4.298134 -1.951186 2.673838 H 6.342899 -1.738340 2.009892 H 5.864044 -2.416881 -0.321473 H 2.215138 -2.339135 3.045793 H 4.508509 -1.668319 3.699984 C -0.808776 -3.663711 0.460046 C -2.087080 -3.342088 0.733614 C -2.433728 -2.124252 1.465430 C -1.299088 -1.225432 1.849850 C -0.007035 -1.603942 1.614924 C 0.310380 -2.833981 0.910508 H -0.551048 -4.560528 -0.093454 H -2.914671 -3.966736 0.413551 H 0.801786 -0.948739 1.911804 C -1.768523 2.151387 3.211930 C -1.492004 3.454162 3.027852 C -0.679149 3.910569 1.898636 C -0.114845 2.857355 0.994021 C -0.393713 1.535007 1.212107 C -1.257236 1.118697 2.303025 H -2.391532 1.806995 4.030626 H -1.875792 4.221456 3.692309 H -0.001570 0.800761 0.516324 C 2.209855 3.492912 -1.764497 C 3.406572 3.165979 -2.279044 C 4.300544 2.231265 -1.587168 C 3.836526 1.695594 -0.267870 C 2.606440 2.044994 0.228723 C 1.738731 2.927331 -0.489519 H 1.536192 4.176968 -2.269603 H 3.746047 3.573497 -3.226883 H 2.279121 1.640632 1.178923 N 1.500267 -3.248030 0.559262 N -1.685218 -0.093956 2.536631 N 0.557751 3.346994 -0.099997 N 4.707736 0.888792 0.373775 N 5.439480 1.825284 -2.026691 N -0.482097 5.172002 1.729371 N -3.672541 -1.861407 1.708392 N 3.455933 -3.060439 -1.291455 H 2.601967 -3.600327 -1.384473 H 4.220649 -3.404616 -1.856644 H -3.732994 -0.961942 2.198332 H 0.088807 5.298581 0.883847 H 4.401425 0.316780 1.147471 H 5.509029 0.564975 -0.149836 H 5.653509 2.252087 -2.931997 C -4.422448 0.318023 -0.572067 C -3.111761 0.601936 -0.883351 C -2.634043 0.205090 -2.153290 C -3.505673 -0.413695 -3.055634
28/46
C -4.849436 -0.689705 -2.730441 C -5.274329 -0.324500 -1.468933 H -2.462711 1.097719 -0.172859 H -3.132401 -0.710850 -4.031058 H -5.516817 -1.175548 -3.433305 O -5.103933 0.603794 0.589711 O -6.520913 -0.467247 -0.898282 C -6.327605 -0.145821 0.490042 C -1.157553 0.356693 -2.447909 H -0.988181 0.454379 -3.526310 H -0.774037 1.267430 -1.973846 C -0.350322 -0.843245 -1.888228 H -0.778136 -1.069775 -0.907463 H -7.159300 0.467523 0.840610 H -6.225308 -1.072180 1.069674 C -0.507647 -2.102932 -2.755682 H 0.048346 -2.937530 -2.315911 H -0.140756 -1.941991 -3.774598 H -1.559122 -2.397081 -2.821747 N 1.043427 -0.453948 -1.616458 C 1.841005 -0.083795 -2.784876 H 1.851154 -0.831853 -3.593677 H 1.480495 0.860716 -3.202056 H 2.874894 0.069691 -2.467823 H 1.504207 -1.238166 -1.161254 Conformer 10 Enthalpy: -1253795.21 C -1.005770 5.669428 0.069577 C -1.097193 4.263893 0.066780 C -1.041145 3.590054 -1.189854 C -0.913517 4.347036 -2.372093 C -0.840801 5.735163 -2.344764 H -0.827536 7.478197 -1.067931 H -1.034695 6.188732 1.024121 H -0.924470 3.819548 -3.320969 H -0.767096 6.295051 -3.271305 C 0.778500 1.735338 -2.548667 C 1.551077 0.783304 -3.107448 C 1.152553 -0.624852 -3.167955 C -0.178985 -0.981250 -2.585028 C -0.935960 0.007851 -2.015797 C -0.505582 1.390609 -1.926558 H 1.124878 2.759614 -2.494728 H 2.524684 1.022893 -3.523449 H -1.930265 -0.202669 -1.646497 C -1.847845 -4.247818 -2.658269 C -2.811141 -4.975313 -2.062884 C -3.395635 -4.576711 -0.779578 C -2.854759 -3.334414 -0.136449 C -1.834910 -2.650515 -0.745481 C -1.366225 -2.995498 -2.068881 H -1.426968 -4.527656 -3.618253 H -3.199602 -5.884717 -2.509698 H -1.379773 -1.812157 -0.236242
29/46
C -4.032740 -1.742625 2.943980 C -4.260642 -0.555996 3.534196 C -4.120075 0.705548 2.796172 C -3.773092 0.605507 1.341056 C -3.604760 -0.632197 0.760910 C -3.640096 -1.838331 1.529107 H -4.108113 -2.676432 3.491003 H -4.535665 -0.492668 4.583044 H -3.406099 -0.687727 -0.300151 N -1.253281 2.205708 -1.222749 N -0.563379 -2.282681 -2.822290 N -3.381351 -3.057660 1.101505 N -3.639553 1.767078 0.666738 N -4.249406 1.881974 3.299363 N -4.322104 -5.301116 -0.254591 N 1.961085 -1.482798 -3.689141 N -1.258773 3.564273 1.250006 H -0.846881 2.626739 1.327215 H -1.095194 4.112722 2.084349 H 1.516289 -2.408398 -3.647181 H -4.593066 -4.873726 0.640465 H -3.542366 2.592941 1.247869 H -3.020836 1.777571 -0.146785 H -4.486332 1.828511 4.293923 C 5.529777 -1.066668 1.719170 C 4.160604 -0.923527 1.799479 C 3.463525 -0.606631 0.609688 C 4.170253 -0.453033 -0.587189 C 5.569495 -0.602479 -0.656606 C 6.222742 -0.909200 0.519205 H 3.638776 -1.053757 2.741710 H 3.624858 -0.227319 -1.497379 H 6.109329 -0.482447 -1.589085 O 6.417424 -1.344362 2.732680 O 7.571487 -1.079595 0.736781 C 7.682986 -1.561292 2.085889 C 1.964215 -0.422734 0.657851 H 1.570095 -0.333172 -0.359670 H 1.500375 -1.314507 1.097055 C 1.496627 0.816335 1.464257 H 1.914716 0.744527 2.476275 H 7.907943 -2.636432 2.074197 H 8.460342 -1.000672 2.610055 C 1.980289 2.128951 0.846830 H 3.068709 2.130118 0.741205 H 1.683298 2.975638 1.471132 H 1.548605 2.274983 -0.146152 N 0.026120 0.834227 1.620983 C -0.452289 -0.027511 2.705639 H -0.101161 -1.069416 2.642874 H -0.120491 0.382026 3.664821 H -1.540961 -0.045371 2.704359 H -0.398870 0.538179 0.743632
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6. Cartesian coordinates and enthalpies for the most stable conformers of interacting MDMA
and tetramer 2 (linear) - the most stable at top of the list:
Conformer 1 Enthalpy: -1253875.33 C 6.965780 0.240861 0.470526 C 5.964098 -0.696444 0.208929 C 5.913229 -1.884367 0.976033 C 6.869260 -2.106083 1.967604 C 7.882027 -1.167445 2.207599 H 8.702111 0.746438 1.642980 H 6.988554 1.156447 -0.114366 H 6.817159 -3.018899 2.555762 H 8.620524 -1.361975 2.979173 C 3.820140 -1.230738 -0.768242 C 2.699604 -0.825475 -1.497082 C 1.502532 -1.538763 -1.437885 C 1.416621 -2.684754 -0.633127 C 2.540129 -3.102702 0.087323 C 3.743291 -2.394583 0.014303 H 2.763438 0.054031 -2.129203 H 2.474781 -3.986538 0.717088 C -0.893184 -1.483124 -1.629886 C -2.028358 -0.711487 -1.871035 C -3.266090 -1.072078 -1.336142 C -3.366631 -2.219677 -0.532620 C -2.221885 -2.979596 -0.269650 C -0.986901 -2.628113 -0.820965 H -1.944638 0.194644 -2.462508 H -2.293690 -3.851075 0.376201 C -5.428966 -0.341603 -0.567539 C -6.301365 0.725835 -0.349542 C -7.310985 0.656125 0.619407 C -7.443283 -0.518302 1.389866 C -6.541842 -1.572181 1.189925 C -5.539128 -1.497261 0.222703 H -6.192722 1.630532 -0.943474 H -6.632308 -2.471470 1.794916 N 4.905648 -2.822159 0.690516 N 0.187796 -3.388228 -0.604812 N -4.640499 -2.566079 -0.024476 N -8.440199 -0.562074 2.391531 N -8.240026 1.703281 0.812747 N -4.429468 -0.301949 -1.573209 N 0.365308 -1.150462 -2.184263 N 5.016032 -0.480431 -0.807525 H -8.573755 -1.495009 2.765542 H -9.333671 -0.213861 2.053511 H -8.409372 1.882058 1.799194 C -0.940237 2.469760 0.868250 C 0.310407 2.927835 1.227475 C 1.173863 3.370011 0.197910 C 0.738846 3.317115 -1.133571 C -0.542417 2.847174 -1.489480 C -1.364860 2.437650 -0.459619 H 0.615068 2.958925 2.267672
31/46
H 1.395265 3.677398 -1.920188 H -0.876530 2.833526 -2.520789 O -1.957409 2.046208 1.690172 O -2.673117 2.009385 -0.513112 C -2.964163 1.519637 0.809450 C 2.559299 3.872302 0.543586 H 2.825397 4.701237 -0.120678 H 2.559587 4.279710 1.560621 C 3.676709 2.788529 0.467176 H 4.608876 3.272648 0.785387 H -3.950580 1.872547 1.114543 H -2.915456 0.423504 0.807642 C 3.395943 1.611532 1.405473 H 3.151212 1.969495 2.410537 H 4.267684 0.957877 1.472852 H 2.551619 1.016173 1.044115 N 3.917065 2.279999 -0.896378 C 4.520623 3.240791 -1.823802 H 4.638526 2.766222 -2.801942 H 3.944187 4.167719 -1.963428 H 5.515363 3.516161 -1.459230 H 3.021762 1.971408 -1.272154 H 4.766621 -3.538218 1.390734 H 4.826220 0.521001 -0.969357 H 0.113871 -4.067207 0.142405 H 0.413761 -0.200171 -2.532561 H -4.619409 -3.266170 0.706510 H -4.215144 0.638519 -1.884708 H -7.949936 2.567423 0.368500 Conformer 2 Enthalpy: -1253873.93 C -8.545453 1.175956 0.047016 C -7.404505 0.440507 -0.271700 C -7.537220 -0.787372 -0.962596 C -8.807490 -1.243331 -1.313364 C -9.947768 -0.488033 -1.005984 H -10.692563 1.312073 -0.079739 H -8.434812 2.113973 0.584851 H -8.902548 -2.191520 -1.836169 H -10.927042 -0.854683 -1.297507 C -5.058808 -0.045322 0.129236 C -3.891032 0.217003 0.847709 C -2.843644 -0.711025 0.889171 C -2.974248 -1.925594 0.193628 C -4.148381 -2.191747 -0.517672 C -5.190114 -1.262419 -0.557416 H -3.786085 1.157784 1.381348 H -4.249655 -3.132315 -1.053147 C -0.516179 -1.184287 1.298322 C 0.753480 -0.734700 1.672296 C 1.904750 -1.447383 1.335980 C 1.791880 -2.641632 0.606415 C 0.523551 -3.098186 0.234375 C -0.629679 -2.389235 0.584333 H 0.847876 0.179506 2.248850
32/46
H 0.432853 -4.018165 -0.338020 C 4.282968 -1.420249 0.936129 C 5.458469 -0.677684 0.872097 C 6.543578 -1.093776 0.089529 C 6.450767 -2.306757 -0.621395 C 5.259603 -3.044890 -0.560786 C 4.174590 -2.614339 0.202839 H 5.522020 0.264449 1.407480 H 5.180685 -3.973812 -1.121299 N -6.366676 -1.484813 -1.306296 N -1.922017 -2.864717 0.266058 N 2.973260 -3.358468 0.304853 N 7.540062 -2.695944 -1.440726 N 7.733322 -0.335070 0.023664 N 3.189338 -1.014176 1.737640 N -1.673165 -0.445134 1.631923 N -6.109549 0.893591 0.033984 H 8.421769 -2.680850 -0.934079 H 7.414137 -3.623176 -1.831846 H 8.160327 -0.386623 -0.897450 C 3.604490 2.463576 -1.475720 C 2.301610 2.910786 -1.546742 C 1.704917 3.401440 -0.361678 C 2.443452 3.402400 0.829580 C 3.776094 2.943340 0.890697 C 4.333830 2.489056 -0.287263 H 1.758734 2.897826 -2.485323 H 1.990543 3.797578 1.734205 H 4.346261 2.974176 1.812313 O 4.397999 1.999541 -2.497113 O 5.621587 2.064198 -0.529178 C 5.598511 1.525061 -1.863399 C 0.274796 3.896596 -0.391675 H 0.165727 4.745686 0.291346 H 0.037432 4.272856 -1.392915 C -0.787286 2.816899 -0.025118 H -1.771480 3.290500 -0.132540 H 6.469329 1.887215 -2.412975 H 5.577345 0.429919 -1.809934 C -0.722765 1.609413 -0.964661 H -0.720426 1.932885 -2.010387 H -1.580729 0.953507 -0.805090 H 0.187274 1.027936 -0.787941 N -0.698444 2.352905 1.372188 C -1.109803 3.332022 2.381654 H -0.986748 2.892519 3.375395 H -0.549552 4.279027 2.357189 H -2.170276 3.566111 2.244191 H 0.268345 2.082437 1.545372 H -6.505017 -2.433505 -1.628029 H -6.063518 1.664494 0.687006 H -1.946926 -3.586105 -0.442915 H -1.469280 0.564397 1.694921 H 2.860718 -4.069524 -0.406662 H 3.224914 -0.037772 2.006455 H 7.571610 0.638593 0.259635
33/46
Conformer 3 Enthalpy: -1253873.93 C -8.545803 1.175748 0.047894 C -7.404841 0.440457 -0.271145 C -7.537557 -0.787288 -0.962283 C -8.807849 -1.243262 -1.312966 C -9.948142 -0.488127 -1.005244 H -10.692946 1.311715 -0.078490 H -8.435150 2.113656 0.585917 H -8.902910 -2.191345 -1.835962 H -10.927429 -0.854797 -1.296697 C -5.059024 -0.045238 0.129278 C -3.891141 0.217043 0.847596 C -2.843639 -0.710872 0.888665 C -2.974223 -1.925284 0.192833 C -4.148463 -2.191399 -0.518307 C -5.190321 -1.262189 -0.557627 H -3.786212 1.157702 1.381461 H -4.249735 -3.131862 -1.053965 C -0.516148 -1.184231 1.297793 C 0.753474 -0.734834 1.672151 C 1.904740 -1.447597 1.335987 C 1.791897 -2.641681 0.606152 C 0.523623 -3.097996 0.233643 C -0.629615 -2.389007 0.583504 H 0.847800 0.179230 2.248959 H 0.432959 -4.017843 -0.338967 C 4.283010 -1.420494 0.936435 C 5.458481 -0.677870 0.872531 C 6.543651 -1.093886 0.089987 C 6.450872 -2.306756 -0.621125 C 5.259682 -3.044867 -0.560757 C 4.174661 -2.614450 0.202920 H 5.522057 0.264143 1.408132 H 5.180789 -3.973696 -1.121427 N -6.367026 -1.484591 -1.306281 N -1.921916 -2.864331 0.264886 N 2.973320 -3.358590 0.304862 N 7.540254 -2.695873 -1.440383 N 7.733469 -0.335244 0.024402 N 3.189338 -1.014795 1.738113 N -1.673111 -0.445032 1.631344 N -6.109888 0.893580 0.034473 H 7.414333 -3.623059 -1.831618 H 8.421894 -2.680900 -0.933617 H 8.160631 -0.386860 -0.896640 C 3.604772 2.463811 -1.475694 C 2.301881 2.910970 -1.547010 C 1.704865 3.401472 -0.362065 C 2.443142 3.402430 0.829369 C 3.775782 2.943458 0.890776 C 4.333814 2.489233 -0.287073 H 1.759252 2.898073 -2.485734 H 1.990019 3.797571 1.733903 H 4.345712 2.974248 1.812539 O 4.398548 1.999834 -2.496951 O 5.621654 2.064383 -0.528682
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C 5.598918 1.525345 -1.862955 C 0.274688 3.896394 -0.392269 H 0.165420 4.745636 0.290531 H 0.037238 4.272345 -1.393603 C -0.787181 2.816548 -0.025487 H -1.771463 3.289957 -0.132937 H 6.469846 1.887596 -2.412293 H 5.577756 0.430203 -1.809548 C -0.722439 1.608956 -0.964892 H -0.719949 1.932285 -2.010659 H -1.580385 0.952996 -0.805408 H 0.187599 1.027544 -0.787941 N -0.698209 2.352724 1.371864 C -1.109437 3.331988 2.381250 H -0.986610 2.892489 3.375021 H -0.548947 4.278848 2.356802 H -2.169834 3.566327 2.243651 H 0.268603 2.082268 1.544974 H -6.505339 -2.433244 -1.628140 H -6.063821 1.664324 0.687678 H -1.946795 -3.585552 -0.444253 H -1.469171 0.564498 1.694400 H 2.860877 -4.069727 -0.406592 H 3.225003 -0.038578 2.007591 H 7.571729 0.638452 0.260239 Conformer 4 Enthalpy: -1253873.93 C -8.545377 1.175521 0.047471 C -7.404399 0.440291 -0.271639 C -7.537109 -0.787593 -0.962523 C -8.807405 -1.243770 -1.312908 C -9.947722 -0.488687 -1.005142 H -10.692550 1.311247 -0.078586 H -8.434742 2.113537 0.585307 H -8.902460 -2.191957 -1.835716 H -10.927020 -0.855507 -1.296368 C -5.058577 -0.045237 0.128767 C -3.890745 0.217164 0.847119 C -2.843289 -0.710797 0.888472 C -2.973892 -1.925380 0.192953 C -4.148089 -2.191614 -0.518210 C -5.189877 -1.262341 -0.557865 H -3.785795 1.157947 1.380760 H -4.249381 -3.132217 -1.053618 C -0.515845 -1.184130 1.297819 C 0.753793 -0.734638 1.672037 C 1.905018 -1.447646 1.336265 C 1.792141 -2.641972 0.606826 C 0.523878 -3.098315 0.234360 C -0.629335 -2.389130 0.583916 H 0.848166 0.179691 2.248409 H 0.433185 -4.018345 -0.337951 C 4.283206 -1.420597 0.936489 C 5.458540 -0.677802 0.872055
35/46
C 6.543513 -1.093845 0.089256 C 6.450675 -2.306882 -0.621579 C 5.259633 -3.045173 -0.560642 C 4.174815 -2.614749 0.203314 H 5.522139 0.264347 1.407404 H 5.180704 -3.974144 -1.121069 N -6.366533 -1.484819 -1.306602 N -1.921656 -2.864518 0.265368 N 2.973597 -3.359076 0.305939 N 7.539850 -2.695979 -1.441135 N 7.733198 -0.335075 0.023094 N 3.189648 -1.014878 1.738302 N -1.672793 -0.444824 1.631122 N -6.109410 0.893602 0.033626 H 7.413909 -3.623244 -1.832182 H 8.421637 -2.680856 -0.934621 H 8.159950 -0.386637 -0.898139 C 3.604274 2.464288 -1.475583 C 2.301415 2.911526 -1.546662 C 1.704540 3.401768 -0.361521 C 2.442906 3.402393 0.829831 C 3.775546 2.943321 0.891008 C 4.333440 2.489378 -0.286995 H 1.758697 2.898920 -2.485337 H 1.989883 3.797326 1.734506 H 4.345547 2.973877 1.812735 O 4.397951 2.000542 -2.496987 O 5.621223 2.064552 -0.528896 C 5.598247 1.525706 -1.863196 C 0.274366 3.896783 -0.391537 H 0.165169 4.745800 0.291559 H 0.036998 4.273122 -1.392747 C -0.787548 2.816922 -0.025114 H -1.771826 3.290326 -0.132640 H 6.469220 1.887793 -2.412579 H 5.576887 0.430544 -1.809963 C -0.722760 1.609433 -0.964657 H -0.720044 1.932908 -2.010379 H -1.580834 0.953584 -0.805422 H 0.187168 1.027877 -0.787632 N -0.698811 2.353012 1.372222 C -1.110882 3.331929 2.381558 H -0.987295 2.892710 3.375356 H -0.551447 4.279407 2.356824 H -2.171583 3.565053 2.244206 H 0.267994 2.082812 1.545709 H -6.504843 -2.433559 -1.628218 H -6.063338 1.664488 0.686669 H -1.946448 -3.585725 -0.443795 H -1.468919 0.564766 1.694143 H 2.861097 -4.070399 -0.405335 H 3.225371 -0.038687 2.007860 H 7.571556 0.638585 0.259120
36/46
Conformer 5 Enthalpy: -1253875.33 C 6.966007 0.241284 0.470073 C 5.964385 -0.696130 0.208640 C 5.913687 -1.883993 0.975861 C 6.869863 -2.105581 1.967302 C 7.882587 -1.166845 2.207112 H 8.702421 0.747078 1.642298 H 6.988605 1.156853 -0.114849 H 6.817909 -3.018362 2.555526 H 8.621211 -1.361280 2.978587 C 3.820398 -1.230697 -0.768322 C 2.699839 -0.825653 -1.497223 C 1.502803 -1.538996 -1.437840 C 1.416973 -2.684807 -0.632853 C 2.540548 -3.102585 0.087614 C 3.743663 -2.394445 0.014403 H 2.763621 0.053697 -2.129565 H 2.475266 -3.986328 0.717516 C -0.892898 -1.483459 -1.629730 C -2.028109 -0.711922 -1.870994 C -3.265792 -1.072376 -1.335923 C -3.366261 -2.219790 -0.532117 C -2.221484 -2.979645 -0.269090 C -0.986542 -2.628264 -0.820558 H -1.944454 0.194037 -2.462745 H -2.293231 -3.850978 0.376965 C -5.428789 -0.341908 -0.567623 C -6.301419 0.725430 -0.350061 C -7.311178 0.655832 0.618735 C -7.443404 -0.518415 1.389495 C -6.541762 -1.572190 1.189981 C -5.538875 -1.497364 0.222920 H -6.192831 1.629976 -0.944237 H -6.632177 -2.471339 1.795189 N 4.906113 -2.821879 0.690557 N 0.188174 -3.388314 -0.604298 N -4.639988 -2.566039 -0.023668 N -8.440457 -0.562063 2.391003 N -8.240434 1.702864 0.811647 N -4.429187 -0.302321 -1.573214 N 0.365552 -1.150856 -2.184305 N 5.016182 -0.480286 -0.807662 H -8.573949 -1.494902 2.765266 H -9.333913 -0.214008 2.052788 H -8.409880 1.881962 1.798016 C -0.940748 2.469798 0.868439 C 0.309912 2.927841 1.227648 C 1.173407 3.369933 0.198088 C 0.738395 3.317004 -1.133395 C -0.542885 2.847112 -1.489286 C -1.365356 2.437672 -0.459414 H 0.614589 2.958927 2.267839 H 1.394842 3.677198 -1.920025 H -0.876990 2.833404 -2.520596 O -1.957964 2.046353 1.690398 O -2.673682 2.009530 -0.512901
37/46
C -2.964829 1.519904 0.809686 C 2.558846 3.872191 0.543780 H 2.824920 4.701236 -0.120360 H 2.559127 4.279446 1.560875 C 3.676349 2.788487 0.467244 H 4.608478 3.272652 0.785502 H -3.951173 1.873013 1.114772 H -2.916271 0.423771 0.807948 C 3.395627 1.611380 1.405422 H 3.150870 1.969210 2.410527 H 4.267374 0.957730 1.472718 H 2.551305 1.016078 1.043972 N 3.916809 2.280113 -0.896326 C 4.519735 3.241200 -1.823843 H 4.638061 2.766571 -2.801902 H 3.942647 4.167698 -1.963645 H 5.514242 3.517348 -1.459223 H 3.021664 1.970942 -1.271993 H 4.767130 -3.537774 1.390957 H 4.826383 0.521068 -0.969746 H 0.114316 -4.067106 0.143096 H 0.413932 -0.200494 -2.532441 H -4.618899 -3.265966 0.707461 H -4.214762 0.638174 -1.884586 H -7.950503 2.566900 0.367093 Conformer 6 Enthalpy: -1253873.98 C 8.094390 1.461493 0.567596 C 7.222031 0.408417 0.295250 C 7.355898 -0.808816 1.004310 C 8.359964 -0.937347 1.963437 C 9.245975 0.119188 2.215794 H 9.790063 2.144089 1.709208 H 7.978678 2.395937 0.024577 H 8.452160 -1.872664 2.509426 H 10.028509 -0.004274 2.957951 C 5.106444 -0.359996 -0.615560 C 3.895578 -0.055671 -1.240177 C 2.816944 -0.947033 -1.197661 C 2.947434 -2.149807 -0.481629 C 4.152349 -2.442152 0.164624 C 5.237479 -1.565953 0.090169 H 3.786005 0.883224 -1.776186 H 4.248207 -3.366333 0.728931 C 0.450725 -1.335681 -1.438938 C -0.822816 -0.844659 -1.740218 C -1.975683 -1.501915 -1.309438 C -1.860463 -2.680217 -0.555146 C -0.588507 -3.178537 -0.255543 C 0.565194 -2.526635 -0.701678 H -0.921125 0.057466 -2.334721 H -0.495960 -4.087028 0.334769 C -4.320731 -1.371072 -0.760558 C -5.462637 -0.583581 -0.646530
38/46
C -6.509265 -0.934553 0.216041 C -6.415823 -2.130081 0.955811 C -5.259191 -2.915356 0.841881 C -4.209556 -2.547933 -0.000350 H -5.526844 0.344041 -1.206409 H -5.179493 -3.831111 1.423534 N 6.485952 -1.864174 0.680104 N 1.856951 -3.046891 -0.460570 N -3.045518 -3.340589 -0.154986 N -7.463560 -2.454157 1.853627 N -7.662975 -0.127791 0.334261 N -3.265682 -1.026212 -1.639126 N 1.610914 -0.654365 -1.869067 N 6.229097 0.493272 -0.695793 H -7.349403 -3.376116 2.260447 H -8.375449 -2.414099 1.405107 H -8.029594 -0.134173 1.282400 C -3.336005 2.588297 1.420018 C -2.018409 2.994277 1.385320 C -1.485696 3.406935 0.141379 C -2.300104 3.376065 -0.998929 C -3.647556 2.960166 -0.951760 C -4.140689 2.582233 0.280791 H -1.415976 3.008264 2.286775 H -1.895371 3.712493 -1.949022 H -4.275894 2.967506 -1.835280 O -4.075268 2.201672 2.511998 O -5.423122 2.216770 0.627028 C -5.325083 1.731882 1.978410 C -0.042050 3.853669 0.054854 H 0.048820 4.661202 -0.679315 H 0.271231 4.273268 1.017207 C 0.960896 2.721511 -0.319259 H 1.963958 3.166188 -0.296749 H -6.149566 2.137790 2.567153 H -5.331792 0.635092 1.969349 C 0.919534 1.564396 0.682954 H 0.996226 1.938662 1.708770 H 1.743975 0.871610 0.502650 H -0.018285 1.007255 0.595447 N 0.769862 2.192810 -1.683289 C 1.151019 3.105627 -2.764357 H 0.952044 2.622898 -3.725172 H 0.625314 4.072490 -2.754395 H 2.225207 3.307055 -2.702873 H -0.214743 1.951350 -1.784273 H 6.485044 -2.640021 1.328993 H 6.042672 1.424804 -1.042923 H 1.903215 -3.754940 0.260747 H 1.444557 0.360008 -1.958493 H -2.912949 -4.034670 0.569619 H -3.279240 -0.053759 -1.924336 H -7.480944 0.831111 0.056164
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Conformer 7 Enthalpy: -1253873.83 C 7.093028 -0.651508 -0.017826 C 5.924370 -1.377702 -0.259128 C 5.803909 -2.686256 0.266295 C 6.852892 -3.233240 1.004377 C 8.030018 -2.503484 1.222340 H 9.051867 -0.634799 0.880744 H 7.172483 0.356861 -0.414375 H 6.747684 -4.237100 1.408071 H 8.839455 -2.949983 1.791557 C 3.588899 -1.398018 -0.867200 C 2.441016 -0.692178 -1.239489 C 1.168496 -1.245726 -1.085863 C 1.034127 -2.529345 -0.532588 C 2.179564 -3.236356 -0.153955 C 3.452664 -2.688668 -0.330489 H 2.536164 0.299739 -1.667924 H 2.078233 -4.227472 0.281226 C -1.219804 -0.911187 -0.901474 C -2.305841 -0.034766 -0.890346 C -3.520757 -0.403010 -0.308529 C -3.654792 -1.673634 0.273564 C -2.570463 -2.556600 0.249269 C -1.354742 -2.189448 -0.334247 H -2.197092 0.957094 -1.317775 H -2.674616 -3.543069 0.694071 C -5.906754 -0.040734 -0.070664 C -7.050798 0.672945 -0.426998 C -8.333700 0.151008 -0.215607 C -8.466617 -1.135032 0.347468 C -7.313553 -1.847539 0.702505 C -6.039091 -1.312191 0.511998 H -6.943963 1.661911 -0.866867 H -7.412964 -2.842030 1.131329 N 4.626681 -3.405163 -0.008956 N -0.261713 -3.081284 -0.412692 N -4.870353 -2.000088 0.911680 N -9.764762 -1.640217 0.586915 N -9.502721 0.843781 -0.609549 N -4.606176 0.503736 -0.227419 N 0.007256 -0.561066 -1.508994 N 4.876097 -0.843139 -1.026278 H -9.763922 -2.632028 0.797844 H -10.387299 -1.471991 -0.199088 H -10.223725 0.808204 0.106672 C -0.104413 2.996456 1.066278 C 1.205902 3.119852 1.480209 C 2.157084 3.568884 0.533982 C 1.746134 3.845913 -0.777038 C 0.405642 3.709361 -1.191664 C -0.501601 3.297661 -0.236721 H 1.492559 2.892552 2.500857 H 2.474935 4.213920 -1.493325 H 0.095619 3.943954 -2.203528 O -1.193706 2.584003 1.796454 O -1.859887 3.109666 -0.361697
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C -2.336080 2.894183 0.981626 C 3.608793 3.724343 0.932462 H 4.050044 4.562746 0.383189 H 3.678066 3.978401 1.995835 C 4.475202 2.453276 0.685589 H 5.496537 2.697097 1.003601 H -2.805615 3.817696 1.346681 H -3.034714 2.056343 0.988899 C 3.987644 1.257579 1.508556 H 3.874156 1.536203 2.561173 H 4.699543 0.431878 1.443836 H 3.019392 0.899574 1.146352 N 4.561873 2.075968 -0.739579 C 5.414018 2.945200 -1.556818 H 5.382886 2.602113 -2.594536 H 5.129205 4.008046 -1.540503 H 6.448023 2.869117 -1.205738 H 3.617687 2.090492 -1.123142 H 4.487925 -4.237157 0.549223 H 4.872120 0.189822 -1.043200 H -0.325163 -3.883911 0.200121 H 0.135531 0.434611 -1.645452 H -5.001211 -2.985433 1.100536 H -4.556706 1.262813 -0.895801 H -9.319069 1.814723 -0.837358 Conformer 8 Enthalpy: -1253873.98 C 8.092843 1.461750 0.568596 C 7.221337 0.408257 0.295417 C 7.355390 -0.809076 1.004158 C 8.358681 -0.937305 1.964148 C 9.243781 0.119718 2.217498 H 9.787479 2.144858 1.711865 H 7.976248 2.396222 0.025802 H 8.450921 -1.872621 2.510202 H 10.025691 -0.003378 2.960433 C 5.106505 -0.360557 -0.616315 C 3.895703 -0.056187 -1.241076 C 2.817021 -0.947469 -1.198339 C 2.947438 -2.150218 -0.482281 C 4.152315 -2.442680 0.164065 C 5.237530 -1.566547 0.089369 H 3.786132 0.882531 -1.777288 H 4.248120 -3.366925 0.728276 C 0.450650 -1.335672 -1.439228 C -0.822922 -0.844420 -1.739863 C -1.975683 -1.501409 -1.308319 C -1.860456 -2.679640 -0.553976 C -0.588431 -3.178410 -0.255359 C 0.565062 -2.526595 -0.702057 H -0.921465 0.057692 -2.334344 H -0.495775 -4.087045 0.334774 C -4.320642 -1.370652 -0.759678 C -5.462588 -0.583334 -0.646124
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C -6.509636 -0.934576 0.215897 C -6.416276 -2.130101 0.955690 C -5.259502 -2.915207 0.842105 C -4.209649 -2.547628 0.000274 H -5.526907 0.344245 -1.206014 H -5.179766 -3.831007 1.423707 N 6.486134 -1.864764 0.679012 N 1.856738 -3.046993 -0.461306 N -3.045517 -3.340114 -0.154075 N -7.464013 -2.454495 1.853408 N -7.663546 -0.128002 0.333913 N -3.265589 -1.025506 -1.638031 N 1.610946 -0.654674 -1.869608 N 6.229141 0.492737 -0.696378 H -7.349820 -3.376664 2.259844 H -8.376033 -2.414083 1.405115 H -8.030311 -0.134415 1.282007 C -3.335815 2.588455 1.419592 C -2.018074 2.994029 1.385299 C -1.484918 3.406409 0.141404 C -2.299023 3.375753 -0.999148 C -3.646595 2.960230 -0.952370 C -4.140172 2.582630 0.280114 H -1.415941 3.007878 2.286916 H -1.893960 3.712064 -1.949161 H -4.274703 2.967718 -1.836063 O -4.075601 2.202419 2.511415 O -5.422906 2.217815 0.626074 C -5.325238 1.732619 1.977345 C -0.041214 3.852990 0.055256 H 0.049776 4.660829 -0.678591 H 0.272026 4.271838 1.017915 C 0.961844 2.721052 -0.318935 H 1.964824 3.165850 -0.295794 H -6.149948 2.138233 2.565971 H -5.331678 0.635847 1.967978 C 0.920157 1.563525 0.682887 H 0.996619 1.936973 1.709071 H 1.744602 0.870800 0.502463 H -0.017636 1.006464 0.594748 N 0.771171 2.192901 -1.683291 C 1.153358 3.105949 -2.763755 H 0.953963 2.623986 -3.724836 H 0.628385 4.073156 -2.753443 H 2.227714 3.306419 -2.702016 H -0.213523 1.952125 -1.785025 H 6.485047 -2.640374 1.328383 H 6.042468 1.424302 -1.043333 H 1.903114 -3.755203 0.259836 H 1.444906 0.359748 -1.958780 H -2.913151 -4.034418 0.570332 H -3.279163 -0.052997 -1.923345 H -7.481661 0.830939 0.055830
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Conformer 9 Enthalpy: -1253873.93 C -8.545564 1.175594 0.047361 C -7.404585 0.440316 -0.271646 C -7.537290 -0.787599 -0.962475 C -8.807581 -1.243767 -1.312899 C -9.947896 -0.488643 -1.005227 H -10.692730 1.311362 -0.078809 H -8.434933 2.113641 0.585146 H -8.902629 -2.191981 -1.835661 H -10.927190 -0.855458 -1.296478 C -5.058772 -0.045222 0.128853 C -3.890939 0.217213 0.847193 C -2.843493 -0.710755 0.888604 C -2.974098 -1.925379 0.193157 C -4.148282 -2.191630 -0.518026 C -5.190069 -1.262359 -0.557726 H -3.785986 1.158024 1.380785 H -4.249572 -3.132255 -1.053397 C -0.516025 -1.184031 1.297882 C 0.753625 -0.734485 1.671981 C 1.904863 -1.447417 1.336086 C 1.791974 -2.641774 0.606690 C 0.523686 -3.098203 0.234399 C -0.629532 -2.389064 0.584041 H 0.848012 0.179843 2.248348 H 0.432982 -4.018267 -0.337858 C 4.283090 -1.420449 0.936379 C 5.458527 -0.677800 0.872116 C 6.543569 -1.093953 0.089473 C 6.450717 -2.307005 -0.621330 C 5.259596 -3.045188 -0.560523 C 4.174687 -2.614625 0.203230 H 5.522130 0.264351 1.407463 H 5.180665 -3.974180 -1.120917 N -6.366715 -1.484869 -1.306465 N -1.921865 -2.864507 0.265640 N 2.973395 -3.358818 0.305626 N 7.539958 -2.696236 -1.440728 N 7.733324 -0.335267 0.023417 N 3.189473 -1.014485 1.737962 N -1.672996 -0.444775 1.631274 N -6.109608 0.893607 0.033687 H 7.414005 -3.623512 -1.831743 H 8.421698 -2.681103 -0.934133 H 8.160088 -0.386781 -0.897818 C 3.604563 2.463909 -1.475671 C 2.301725 2.911221 -1.546750 C 1.704916 3.401612 -0.361636 C 2.443312 3.402287 0.829699 C 3.775923 2.943130 0.890881 C 4.333771 2.489084 -0.287110 H 1.758975 2.898555 -2.485406 H 1.990312 3.797277 1.734360 H 4.345956 2.973699 1.812589 O 4.398189 2.000037 -2.497058 O 5.621537 2.064218 -0.529006
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C 5.598502 1.525225 -1.863264 C 0.274810 3.896842 -0.391678 H 0.165752 4.745891 0.291399 H 0.037534 4.273213 -1.392899 C -0.787310 2.817183 -0.025268 H -1.771505 3.290742 -0.132880 H 6.469469 1.887230 -2.412707 H 5.577092 0.430071 -1.809900 C -0.722648 1.609617 -0.964712 H -0.719979 1.932993 -2.010465 H -1.580740 0.953821 -0.805352 H 0.187266 1.028038 -0.787686 N -0.698758 2.353304 1.372114 C -1.110557 3.332430 2.381391 H -0.987645 2.893039 3.375197 H -0.550486 4.279538 2.356954 H -2.171047 3.566269 2.243648 H 0.268013 2.082960 1.545610 H -6.505021 -2.433614 -1.628069 H -6.063551 1.664516 0.686703 H -1.946715 -3.585850 -0.443384 H -1.469164 0.564790 1.694316 H 2.860885 -4.070125 -0.405655 H 3.225184 -0.038222 2.007259 H 7.571736 0.638390 0.259500 Conformer 10 Enthalpy: -1253873.93 C -8.545447 1.175615 0.047279 C -7.404475 0.440330 -0.271730 C -7.537193 -0.787605 -0.962519 C -8.807488 -1.243788 -1.312902 C -9.947799 -0.488656 -1.005232 H -10.692614 1.311377 -0.078856 H -8.434809 2.113679 0.585033 H -8.902547 -2.192017 -1.835633 H -10.927096 -0.855482 -1.296452 C -5.058680 -0.045232 0.128808 C -3.890874 0.217181 0.847197 C -2.843470 -0.710830 0.888687 C -2.974081 -1.925467 0.193274 C -4.148240 -2.191699 -0.517962 C -5.189990 -1.262394 -0.557733 H -3.785910 1.158005 1.380763 H -4.249533 -3.132330 -1.053323 C -0.516013 -1.184120 1.297980 C 0.753641 -0.734514 1.671982 C 1.904884 -1.447387 1.335997 C 1.791995 -2.641749 0.606602 C 0.523699 -3.098232 0.234402 C -0.629527 -2.389148 0.584148 H 0.848025 0.179836 2.248313 H 0.432998 -4.018287 -0.337869 C 4.283114 -1.420385 0.936248 C 5.458577 -0.677778 0.872042
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C 6.543648 -1.093954 0.089449 C 6.450809 -2.307009 -0.621334 C 5.259665 -3.045168 -0.560569 C 4.174720 -2.614569 0.203108 H 5.522179 0.264372 1.407390 H 5.180742 -3.974164 -1.120957 N -6.366615 -1.484877 -1.306514 N -1.921873 -2.864607 0.265844 N 2.973415 -3.358738 0.305442 N 7.540074 -2.696280 -1.440682 N 7.733394 -0.335247 0.023453 N 3.189489 -1.014377 1.737782 N -1.672996 -0.444878 1.631443 N -6.109488 0.893621 0.033559 H 7.414088 -3.623540 -1.831722 H 8.421789 -2.681227 -0.934044 H 8.160357 -0.386993 -0.897674 C 3.604499 2.464005 -1.475603 C 2.301650 2.911283 -1.546714 C 1.704781 3.401642 -0.361614 C 2.443142 3.402351 0.829738 C 3.775780 2.943271 0.890947 C 4.333673 2.489213 -0.287017 H 1.758921 2.898570 -2.485380 H 1.990108 3.797325 1.734388 H 4.345791 2.973873 1.812667 O 4.398156 2.000153 -2.496953 O 5.621447 2.064376 -0.528883 C 5.598497 1.525409 -1.863145 C 0.274629 3.896758 -0.391711 H 0.165486 4.745830 0.291325 H 0.037367 4.273074 -1.392955 C -0.787393 2.817027 -0.025302 H -1.771638 3.290460 -0.133000 H 6.469446 1.887490 -2.412566 H 5.577157 0.430253 -1.809807 C -0.722556 1.609415 -0.964677 H -0.719853 1.932742 -2.010447 H -1.580597 0.953552 -0.805341 H 0.187398 1.027929 -0.787568 N -0.698878 2.353260 1.372132 C -1.111076 3.332366 2.381265 H -0.988071 2.893144 3.375134 H -0.551334 4.279664 2.356743 H -2.171641 3.565820 2.243434 H 0.267937 2.083183 1.545780 H -6.504934 -2.433624 -1.628105 H -6.063413 1.664573 0.686523 H -1.946777 -3.586103 -0.443017 H -1.469116 0.564693 1.694337 H 2.860906 -4.070050 -0.405830 H 3.225180 -0.038095 2.007006 H 7.571694 0.638472 0.259210
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7. Figure S3. Square wave voltammograms after 10 minutes of incubation with 50 μL of 100
μmol L-1 epinephrine, norepinephrine, dopamine, tyramine, amphetamine,
methamphetamine, caffeine and MDMA. Polymerization conditions: 0.50 mmol L-1 o-PD,
2.0 mmol L-1 MDMA and 5 scanning cycles. SWV was performed in the potential range of
0.0 to +1.6 V, at a frequency of 25 Hz. The SWVs had their baseline corrected by the
‘moving average’ feature present in the GPES software.
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8. Figure S4. Calibration curves for urine (1:10) and serum (1:20).
