Post on 05-Aug-2019
Thieme
Supporting Information for DOI: 10.1055/s-0037-1610631
© Georg Thieme Verlag KG Stuttgart · New York 2018
Supplementary Material
Novel and convenient synthesis of dialkyl as-indacene Rodrigo Faúndez,1 Francisco Castillo,1 Marcelo Preite, 4, Eduardo Schott,1 Ximena Zarate,5
Juan Manuel Manriquez, E. Molins3, Cesar Morales-Verdejo*,2 Ivonne Chávez*1
S1: 1H NMR of compound 1a in chloroform-d.
S2: 13C NMR of compound 1a in chloroform-d.
S3: 1H NMR of compound 2a in DMSO- d6.
S4: 13C NMR of compound 2a in DMSO- d6.
S5: 1 H NMR of compound 3a in DMSO- d6.
S6: 13C NMR of compound 3a in DMSO-d6.
S7: 1H NMR of compound 4a in Chloroform-d.
S8: 13C NMR of compound 4a in chloroform-d.
S9: IR of compound 5a in KBr.
S10: 1H NMR of compound 6a in chloroform-d.
S11: 13C NMR of compound 6a in chloroform-.
S12: FT-IR of compound 6a in KBr.
S13: High resolution mass spectroscopy of compound 6a
6a #1 RT: 0.01 AV: 1 NL: 9.17E7T: FTMS + p ESI Full ms [170.0000-200.0000]
173 174 175 176 177 178 179 180 181 182 183 184 185 186 187 188 189 190 191 192 193m/z
0
5
10
15
20
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30
35
40
45
50
55
60
65
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85
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Rel
ativ
e Abu
ndan
ce
183.
1170
184.
1201
187.
0754
S14: 1H NMR of compound 1b in chloroform-d.
S15: 13C NMR of compound 1b in chloroform-d.
S16: 1H NMR of compound 2b in DMSO-d6
S17: 13C NMR of compound 2b in DMSO-d6
S18: 1H NMR of compound 3b in DMSO-d6
S19: 13C NMR of compound 3b in DMSO –d6
S20: 1H NMR of compound 4b in chloroform-d
S21: 13C NMR of compound 4b in chloroform-d.
S22: FT-IR of compound 5b in KBr.
S23: 1H NMR of compound 6b in chloroform-d.
S24: 13C NMR of compound 6b in chloroform-d.
S25: IR of compound 6b in KBr.
S26: High resolution mass spectroscopy of compound 6b
6b #1 RT: 0.01 AV: 1 NL: 6.63E7T: FTMS + p ESI Full ms [200.0000-225.0000]
201 202 203 204 205 206 207 208 209 210 211 212 213 214 215 216 217 218 219 220 221m/z
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Rel
ativ
e Abu
ndan
ce
211.
1481
212.
1514
210.
1405
209.
1327
S27: Unit cell of the compound 5a. Unit Cell Parameters: a 22.296(6) b 5.524(7) c 18.887(5) C2/c (Deposition number CCDC 1821144) Crystallographic data Deposition number CCDC 1821144
Table S1. Crystal data and structure refinement for 5a.
Identification code Ch36
Empirical formula C14 H14
Formula weight 182.25
Temperature 293(2) K
Wavelength 0.71073 Å
Crystal system Monoclinic
Space group C 2/c
Unit cell dimensions a = 22.296(6) Å = 90°.
b = 5.524(7) Å = 115.724(19)°.
c = 18.887(5) Å = 90°.
Volume 2096(3) Å3
Z 8
Density (calculated) 1.155 Mg/m3
Absorption coefficient 0.065 mm-1
F(000) 784
Crystal size 0.45 x 0.39 x 0.30 mm3
Theta range for data collection 2.028 to 24.974°.
Index ranges 0<=h<=6, -13<=k<=13, -20<=l<=20
Reflections collected 1851
Independent reflections 1851 [R(int) = 0.0419]
Completeness to theta = 24.974° 100.0 %
Refinement method Full-matrix least-squares on F2
Data / restraints / parameters 1851 / 0 / 129
Goodness-of-fit on F2 1.064
Final R indices [I>2sigma(I)] R1 = 0.0424, wR2 = 0.1090
R indices (all data) R1 = 0.0687, wR2 = 0.1177
Largest diff. peak and hole 0.096 and -0.112 e.Å-3
Table S2. Atomic coordinates ( x 104) and equivalent isotropic displacement parameters (Å2x 103)
for ch36. U(eq) is defined as one third of the trace of the orthogonalized Uij tensor.
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x y z U(eq)
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C(1) 4424(1) 548(3) 10395(1) 76(1)
C(2) 4138(1) -1169(3) 10646(1) 70(1)
C(3) 3398(1) -1111(3) 10168(1) 66(1)
C(4) 3297(1) 948(3) 9597(1) 60(1)
C(5) 2735(1) 1896(3) 9013(1) 61(1)
C(6) 2010(1) 1252(3) 8707(1) 66(1)
C(7) 1669(1) 3050(3) 8058(1) 70(1)
C(8) 2121(1) 4487(3) 7992(1) 75(1)
C(9) 2791(1) 3855(3) 8566(1) 67(1)
C(10) 3410(1) 4799(4) 8714(1) 84(1)
C(11) 3978(1) 3825(3) 9302(1) 82(1)
C(12) 3922(1) 1891(3) 9747(1) 68(1)
C(13) 4476(1) -2966(3) 11286(1) 89(1)
C(14) 934(1) 3072(4) 7573(1) 95(1)
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Table S3. Bond lengths [Å] and angles [°] for 5a.
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C(1)-C(2) 1.339(2)
C(1)-C(12) 1.453(2)
C(2)-C(13) 1.491(2)
C(2)-C(3) 1.498(2)
C(3)-C(4) 1.515(2)
C(4)-C(5) 1.365(2)
C(4)-C(12) 1.395(2)
C(5)-C(9) 1.412(2)
C(5)-C(6) 1.503(2)
C(6)-C(7) 1.504(2)
C(7)-C(8) 1.331(3)
C(7)-C(14) 1.489(2)
C(8)-C(9) 1.456(2)
C(9)-C(10) 1.386(2)
C(10)-C(11) 1.380(3)
C(11)-C(12) 1.398(3)
C(2)-C(1)-C(12) 110.41(16)
C(1)-C(2)-C(13) 127.35(17)
C(1)-C(2)-C(3) 109.90(15)
C(13)-C(2)-C(3) 122.74(16)
C(2)-C(3)-C(4) 103.24(14)
C(5)-C(4)-C(12) 120.45(15)
C(5)-C(4)-C(3) 131.54(15)
C(12)-C(4)-C(3) 108.01(14)
C(4)-C(5)-C(9) 119.28(15)
C(4)-C(5)-C(6) 132.61(15)
C(9)-C(5)-C(6) 108.11(14)
C(5)-C(6)-C(7) 103.70(14)
C(8)-C(7)-C(14) 127.87(17)
C(8)-C(7)-C(6) 109.48(16)
C(14)-C(7)-C(6) 122.63(18)
C(7)-C(8)-C(9) 111.22(16)
C(10)-C(9)-C(5) 120.46(16)
C(10)-C(9)-C(8) 132.06(17)
C(5)-C(9)-C(8) 107.48(16)
C(11)-C(10)-C(9) 120.02(17)
C(10)-C(11)-C(12) 119.50(19)
C(4)-C(12)-C(11) 120.30(17)
C(4)-C(12)-C(1) 108.44(15)
C(11)-C(12)-C(1) 131.26(18)
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Table S4. Anisotropic displacement parameters (Å2x 103) for 5a. The anisotropic
displacement factor exponent takes the form: -2π2[ h2a*2U11 + ... + 2 h k a* b* U12 ]
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U11 U22 U33 U23 U13 U12
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C(1) 79(1) 77(1) 73(1) -16(1) 35(1) -12(1)
C(2) 88(1) 60(1) 64(1) -10(1) 33(1) -5(1)
C(3) 88(1) 51(1) 66(1) -3(1) 40(1) -4(1)
C(4) 85(1) 49(1) 56(1) -9(1) 41(1) -9(1)
C(5) 90(1) 47(1) 54(1) -8(1) 40(1) -6(1)
C(6) 89(1) 51(1) 65(1) -4(1) 40(1) 3(1)
C(7) 98(1) 59(1) 60(1) -5(1) 40(1) 11(1)
C(8) 121(1) 55(1) 61(1) 4(1) 49(1) 8(1)
C(9) 103(1) 53(1) 56(1) -6(1) 45(1) -7(1)
C(10) 126(2) 70(1) 74(1) 1(1) 61(1) -20(1)
C(11) 101(1) 80(1) 77(1) -8(1) 51(1) -27(1)
C(12) 90(1) 63(1) 63(1) -14(1) 44(1) -19(1)
C(13) 99(1) 73(1) 83(1) 2(1) 29(1) 4(1)
C(14) 106(2) 95(2) 83(1) 2(1) 40(1) 24(2) Table S5.
Comp. H 6a 6b exp.
C4-C5 1.384 1.382 1.382 1.365
C11-C10 1.399 1.401 1.401 1.38
C4-C12 1.421 1.422 1.421 1.404a
C12-C11 1.402 1.400 1.400 1.392a
C12-C1 1.462 1.460 1.460 1.455a
C4-C3 1.509 1.509 1.509 1.509a
C1-C2 1.353 1.356 1.357 1.335a
C2-C3 1.510 1.517 1.518 1.501a
C2-C13 - 1.492 1.497 1.490a
C13-C15 - - 1.528 - aMean value