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

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183.

1170

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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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211.

1481

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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