organic compounds
2-[4,5-Bis(ethylsulfanyl)-1,3-dithiol-2-ylidene]-5-(4-methoxyphenyl)-5H-1,3-dithiolo[4,5-c]pyrrole
aKey Laboratory of Organism Functional Factors of Changbai Mountain, Yanbian University, Ministry of Education, Yanji 133002, People's Republic of China, and bState Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, People's Republic of China
*Correspondence e-mail: zqcong@ybu.edu.cn
The 19H19NOS6, contains two independent molecules with different conformations of the ethyl groups. The dihedral angles between the pyrrole and benzene rings are 14.19 (14) and 16.29 (17)° in the two molecules. In the absence of short intermolecular contacts, in the crystal, the molecules are packed with their long axes parallel to [10].
of the title compound, CRelated literature
For general background to the use of pyrrolo-tetrathiafulvalene derivatives as building blocks in supramolecular and materials chemistry, see Becher et al. (2004). For details of the synthesis, see Yin et al. (2004).
Experimental
Crystal data
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Data collection: RAPID-AUTO (Rigaku, 1998); cell RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536809047424/cv2638sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809047424/cv2638Isup2.hkl
The title compound was prepared through cross-coupling reaction of 4,5-bis(ethylthio)-1,3-dithiole-2-thione with N-(4-methoxyphenyl)-(1,3)-dithiolo[4,5-c]pyrrole-2-one (Yin et al., 2004). Single crystals for X-ray diffraction were pepared by slow evaporation a mixture of dichloromethane and petroleum at room temperature.
C-bound H-atoms were placed in calculated positions (C—H 0.93-0.97 Å), and were included in the
in the riding model, with Uiso(H) = 1.5 or 1.2 Ueq(C).Data collection: RAPID-AUTO (Rigaku, 1998); cell
RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).Fig. 1. Two independent molecules of the title compound, with the atom numbering and 30% probalility displacement ellipsoids. |
C19H19NOS6 | Z = 4 |
Mr = 469.71 | F(000) = 976 |
Triclinic, P1 | Dx = 1.469 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.974 (2) Å | Cell parameters from 14243 reflections |
b = 12.121 (2) Å | θ = 3.1–27.5° |
c = 16.762 (3) Å | µ = 0.65 mm−1 |
α = 73.90 (3)° | T = 291 K |
β = 85.53 (3)° | Block, yellow |
γ = 65.43 (3)° | 0.14 × 0.13 × 0.12 mm |
V = 2123.8 (7) Å3 |
Rigaku R-AXIS RAPID diffractometer | 9633 independent reflections |
Radiation source: fine-focus sealed tube | 6504 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ω scans | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −15→13 |
Tmin = 0.914, Tmax = 0.926 | k = −15→15 |
21057 measured reflections | l = −21→21 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.117 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0602P)2] where P = (Fo2 + 2Fc2)/3 |
9633 reflections | (Δ/σ)max = 0.001 |
493 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C19H19NOS6 | γ = 65.43 (3)° |
Mr = 469.71 | V = 2123.8 (7) Å3 |
Triclinic, P1 | Z = 4 |
a = 11.974 (2) Å | Mo Kα radiation |
b = 12.121 (2) Å | µ = 0.65 mm−1 |
c = 16.762 (3) Å | T = 291 K |
α = 73.90 (3)° | 0.14 × 0.13 × 0.12 mm |
β = 85.53 (3)° |
Rigaku R-AXIS RAPID diffractometer | 9633 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 6504 reflections with I > 2σ(I) |
Tmin = 0.914, Tmax = 0.926 | Rint = 0.033 |
21057 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.117 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.31 e Å−3 |
9633 reflections | Δρmin = −0.27 e Å−3 |
493 parameters |
Experimental. (See detailed section in the paper) |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.0187 (3) | 0.4802 (3) | 0.7889 (2) | 0.0854 (10) | |
H1A | 0.0726 | 0.5120 | 0.8044 | 0.128* | |
H1B | −0.0388 | 0.4759 | 0.8316 | 0.128* | |
H1C | −0.0252 | 0.5354 | 0.7376 | 0.128* | |
C2 | 0.1669 (2) | 0.3475 (2) | 0.71499 (16) | 0.0515 (6) | |
C3 | 0.2258 (2) | 0.2272 (2) | 0.70449 (18) | 0.0602 (7) | |
H3 | 0.2079 | 0.1622 | 0.7386 | 0.072* | |
C4 | 0.3105 (2) | 0.2030 (2) | 0.64426 (17) | 0.0571 (7) | |
H4 | 0.3494 | 0.1219 | 0.6378 | 0.069* | |
C5 | 0.3380 (2) | 0.2985 (2) | 0.59338 (15) | 0.0442 (5) | |
C6 | 0.2771 (2) | 0.4189 (2) | 0.60244 (16) | 0.0548 (6) | |
H6 | 0.2939 | 0.4841 | 0.5676 | 0.066* | |
C7 | 0.1915 (2) | 0.4437 (2) | 0.66262 (17) | 0.0563 (7) | |
H7 | 0.1505 | 0.5254 | 0.6678 | 0.068* | |
C8 | 0.5125 (2) | 0.1538 (2) | 0.52980 (15) | 0.0486 (6) | |
H8 | 0.5188 | 0.0776 | 0.5659 | 0.058* | |
C9 | 0.5849 (2) | 0.1689 (2) | 0.46494 (14) | 0.0442 (5) | |
C10 | 0.5441 (2) | 0.2991 (2) | 0.42581 (14) | 0.0446 (5) | |
C11 | 0.4482 (2) | 0.3611 (2) | 0.46830 (15) | 0.0476 (6) | |
H11 | 0.4041 | 0.4480 | 0.4564 | 0.057* | |
C12 | 0.7299 (2) | 0.1887 (2) | 0.34512 (14) | 0.0430 (5) | |
C13 | 0.8184 (2) | 0.1662 (2) | 0.29066 (15) | 0.0444 (5) | |
C14 | 0.9907 (2) | 0.0657 (2) | 0.19511 (15) | 0.0469 (6) | |
C15 | 1.0237 (3) | −0.1466 (2) | 0.1501 (2) | 0.0684 (8) | |
H15A | 1.0782 | −0.2149 | 0.1275 | 0.082* | |
H15B | 1.0068 | −0.1837 | 0.2063 | 0.082* | |
C16 | 0.9051 (3) | −0.0780 (3) | 0.09887 (18) | 0.0773 (9) | |
H16A | 0.8485 | −0.0134 | 0.1226 | 0.116* | |
H16B | 0.8705 | −0.1364 | 0.0981 | 0.116* | |
H16C | 0.9205 | −0.0405 | 0.0431 | 0.116* | |
C17 | 0.9521 (2) | 0.1906 (2) | 0.16305 (15) | 0.0485 (6) | |
C18 | 1.1509 (3) | 0.2438 (3) | 0.0997 (2) | 0.0904 (12) | |
H18A | 1.1488 | 0.2678 | 0.1506 | 0.109* | |
H18B | 1.2049 | 0.1551 | 0.1099 | 0.109* | |
C19 | 1.1992 (3) | 0.3184 (4) | 0.0333 (3) | 0.1182 (16) | |
H19A | 1.2185 | 0.2824 | −0.0130 | 0.177* | |
H19B | 1.2721 | 0.3178 | 0.0538 | 0.177* | |
H19C | 1.1384 | 0.4035 | 0.0158 | 0.177* | |
C20 | −0.5385 (3) | 0.8748 (3) | 0.7996 (2) | 0.0770 (9) | |
H20A | −0.5821 | 0.8834 | 0.7511 | 0.116* | |
H20B | −0.5959 | 0.9151 | 0.8368 | 0.116* | |
H20C | −0.4941 | 0.7871 | 0.8270 | 0.116* | |
C21 | −0.3663 (2) | 0.8889 (2) | 0.72209 (15) | 0.0460 (5) | |
C22 | −0.3512 (2) | 0.7916 (2) | 0.68927 (16) | 0.0537 (6) | |
H22 | −0.4039 | 0.7510 | 0.7029 | 0.064* | |
C23 | −0.2572 (2) | 0.7543 (2) | 0.63580 (17) | 0.0535 (6) | |
H23 | −0.2467 | 0.6880 | 0.6142 | 0.064* | |
C24 | −0.17888 (19) | 0.8141 (2) | 0.61409 (13) | 0.0402 (5) | |
C25 | −0.1954 (2) | 0.9128 (2) | 0.64690 (15) | 0.0469 (5) | |
H25 | −0.1438 | 0.9546 | 0.6325 | 0.056* | |
C26 | −0.2882 (2) | 0.9490 (2) | 0.70089 (16) | 0.0517 (6) | |
H26 | −0.2983 | 1.0146 | 0.7232 | 0.062* | |
C27 | −0.0765 (2) | 0.7044 (2) | 0.50572 (14) | 0.0450 (5) | |
H27 | −0.1322 | 0.6706 | 0.5018 | 0.054* | |
C28 | 0.0251 (2) | 0.6924 (2) | 0.46045 (14) | 0.0424 (5) | |
C29 | 0.0835 (2) | 0.7582 (2) | 0.48538 (14) | 0.0414 (5) | |
C30 | 0.0163 (2) | 0.8089 (2) | 0.54558 (15) | 0.0448 (5) | |
H30 | 0.0336 | 0.8573 | 0.5731 | 0.054* | |
C31 | 0.21143 (19) | 0.6709 (2) | 0.36860 (14) | 0.0403 (5) | |
C32 | 0.2935 (2) | 0.6418 (2) | 0.31059 (14) | 0.0408 (5) | |
C33 | 0.4041 (2) | 0.5729 (2) | 0.18181 (14) | 0.0435 (5) | |
C34 | 0.3035 (2) | 0.5950 (3) | 0.03313 (16) | 0.0587 (7) | |
H34A | 0.3066 | 0.5558 | −0.0107 | 0.070* | |
H34B | 0.2317 | 0.5971 | 0.0648 | 0.070* | |
C35 | 0.2904 (3) | 0.7273 (3) | −0.00531 (19) | 0.0732 (9) | |
H35A | 0.2825 | 0.7683 | 0.0376 | 0.110* | |
H35B | 0.2185 | 0.7724 | −0.0419 | 0.110* | |
H35C | 0.3616 | 0.7259 | −0.0362 | 0.110* | |
C36 | 0.4630 (2) | 0.6343 (2) | 0.20262 (15) | 0.0450 (5) | |
C37 | 0.5531 (3) | 0.8156 (3) | 0.1410 (2) | 0.0684 (8) | |
H37A | 0.5403 | 0.8307 | 0.1955 | 0.082* | |
H37B | 0.6228 | 0.8334 | 0.1184 | 0.082* | |
C38 | 0.4416 (3) | 0.9048 (3) | 0.0860 (2) | 0.0906 (11) | |
H38A | 0.4501 | 0.8856 | 0.0334 | 0.136* | |
H38B | 0.4331 | 0.9896 | 0.0776 | 0.136* | |
H38C | 0.3701 | 0.8964 | 0.1118 | 0.136* | |
N1 | 0.42782 (17) | 0.27241 (16) | 0.53236 (12) | 0.0454 (5) | |
N2 | −0.08223 (16) | 0.77573 (17) | 0.55855 (11) | 0.0421 (4) | |
O1 | 0.08803 (17) | 0.35935 (18) | 0.77861 (12) | 0.0664 (5) | |
O2 | −0.45483 (16) | 0.93211 (17) | 0.77612 (12) | 0.0638 (5) | |
S1 | 0.71479 (6) | 0.06700 (5) | 0.42617 (4) | 0.05735 (19) | |
S2 | 0.62565 (6) | 0.34433 (6) | 0.34207 (4) | 0.05800 (19) | |
S3 | 0.92856 (6) | 0.01481 (5) | 0.29013 (4) | 0.05201 (17) | |
S4 | 0.84103 (7) | 0.28873 (6) | 0.21607 (4) | 0.05770 (18) | |
S5 | 1.10304 (6) | −0.04916 (7) | 0.15474 (5) | 0.0687 (2) | |
S6 | 0.99851 (6) | 0.26916 (7) | 0.07115 (4) | 0.06066 (19) | |
S7 | 0.09330 (6) | 0.61643 (7) | 0.38385 (4) | 0.05587 (17) | |
S8 | 0.21920 (5) | 0.75478 (6) | 0.43717 (4) | 0.04944 (16) | |
S9 | 0.29160 (6) | 0.54706 (6) | 0.24866 (4) | 0.05071 (16) | |
S10 | 0.42090 (5) | 0.68105 (6) | 0.29521 (4) | 0.05067 (16) | |
S11 | 0.43992 (6) | 0.49999 (6) | 0.10086 (4) | 0.05701 (18) | |
S12 | 0.59037 (6) | 0.65155 (7) | 0.15249 (5) | 0.06202 (19) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.097 (2) | 0.081 (2) | 0.105 (3) | −0.0512 (19) | 0.042 (2) | −0.051 (2) |
C2 | 0.0554 (14) | 0.0509 (13) | 0.0568 (15) | −0.0296 (12) | 0.0023 (12) | −0.0155 (12) |
C3 | 0.0663 (16) | 0.0521 (14) | 0.0682 (18) | −0.0355 (13) | 0.0141 (13) | −0.0110 (13) |
C4 | 0.0640 (15) | 0.0417 (13) | 0.0671 (17) | −0.0263 (12) | 0.0062 (13) | −0.0106 (12) |
C5 | 0.0444 (12) | 0.0428 (12) | 0.0471 (13) | −0.0218 (10) | −0.0045 (10) | −0.0069 (10) |
C6 | 0.0663 (16) | 0.0430 (13) | 0.0565 (16) | −0.0290 (12) | 0.0068 (12) | −0.0063 (11) |
C7 | 0.0628 (15) | 0.0441 (13) | 0.0652 (17) | −0.0250 (12) | 0.0078 (13) | −0.0163 (12) |
C8 | 0.0563 (14) | 0.0358 (11) | 0.0489 (14) | −0.0186 (11) | −0.0008 (11) | −0.0040 (10) |
C9 | 0.0487 (12) | 0.0357 (11) | 0.0456 (13) | −0.0168 (10) | −0.0052 (10) | −0.0059 (10) |
C10 | 0.0519 (13) | 0.0376 (11) | 0.0430 (13) | −0.0217 (10) | −0.0054 (10) | −0.0017 (10) |
C11 | 0.0511 (13) | 0.0357 (11) | 0.0506 (14) | −0.0172 (10) | −0.0017 (11) | −0.0034 (10) |
C12 | 0.0507 (12) | 0.0396 (11) | 0.0398 (12) | −0.0202 (10) | −0.0027 (10) | −0.0083 (9) |
C13 | 0.0537 (13) | 0.0408 (11) | 0.0429 (13) | −0.0234 (10) | −0.0028 (10) | −0.0102 (10) |
C14 | 0.0464 (12) | 0.0482 (13) | 0.0483 (14) | −0.0248 (11) | 0.0054 (10) | −0.0088 (11) |
C15 | 0.0791 (18) | 0.0409 (13) | 0.081 (2) | −0.0226 (13) | 0.0314 (16) | −0.0208 (13) |
C16 | 0.108 (2) | 0.079 (2) | 0.0578 (19) | −0.0528 (19) | 0.0120 (17) | −0.0171 (16) |
C17 | 0.0498 (13) | 0.0501 (13) | 0.0482 (14) | −0.0272 (11) | 0.0007 (10) | −0.0064 (11) |
C18 | 0.0609 (18) | 0.090 (2) | 0.104 (3) | −0.0400 (17) | −0.0002 (17) | 0.012 (2) |
C19 | 0.091 (2) | 0.121 (3) | 0.145 (4) | −0.071 (2) | 0.028 (2) | −0.001 (3) |
C20 | 0.0716 (18) | 0.076 (2) | 0.090 (2) | −0.0347 (16) | 0.0337 (17) | −0.0331 (18) |
C21 | 0.0497 (13) | 0.0392 (11) | 0.0452 (13) | −0.0149 (10) | 0.0014 (10) | −0.0109 (10) |
C22 | 0.0571 (14) | 0.0534 (14) | 0.0618 (17) | −0.0319 (12) | 0.0115 (12) | −0.0207 (12) |
C23 | 0.0632 (15) | 0.0511 (13) | 0.0640 (17) | −0.0353 (12) | 0.0140 (12) | −0.0270 (12) |
C24 | 0.0464 (12) | 0.0398 (11) | 0.0371 (12) | −0.0201 (10) | −0.0018 (9) | −0.0096 (9) |
C25 | 0.0566 (13) | 0.0463 (12) | 0.0486 (14) | −0.0304 (11) | 0.0012 (11) | −0.0143 (11) |
C26 | 0.0631 (15) | 0.0442 (12) | 0.0562 (16) | −0.0250 (12) | 0.0028 (12) | −0.0218 (11) |
C27 | 0.0539 (13) | 0.0515 (13) | 0.0463 (13) | −0.0345 (11) | 0.0056 (10) | −0.0188 (11) |
C28 | 0.0517 (13) | 0.0451 (12) | 0.0401 (12) | −0.0282 (11) | 0.0034 (10) | −0.0136 (10) |
C29 | 0.0483 (12) | 0.0445 (12) | 0.0380 (12) | −0.0263 (10) | −0.0039 (9) | −0.0079 (10) |
C30 | 0.0511 (13) | 0.0500 (13) | 0.0487 (14) | −0.0316 (11) | 0.0014 (10) | −0.0192 (11) |
C31 | 0.0440 (12) | 0.0385 (11) | 0.0403 (12) | −0.0202 (10) | −0.0037 (9) | −0.0068 (9) |
C32 | 0.0454 (12) | 0.0389 (11) | 0.0388 (12) | −0.0190 (10) | −0.0021 (9) | −0.0078 (9) |
C33 | 0.0435 (12) | 0.0371 (11) | 0.0421 (13) | −0.0107 (10) | 0.0009 (9) | −0.0076 (9) |
C34 | 0.0603 (15) | 0.0762 (18) | 0.0533 (16) | −0.0344 (14) | 0.0063 (12) | −0.0293 (14) |
C35 | 0.0787 (19) | 0.0650 (18) | 0.0669 (19) | −0.0230 (16) | −0.0143 (15) | −0.0098 (15) |
C36 | 0.0445 (12) | 0.0421 (12) | 0.0453 (13) | −0.0165 (10) | 0.0035 (10) | −0.0095 (10) |
C37 | 0.0676 (17) | 0.0814 (19) | 0.081 (2) | −0.0502 (16) | 0.0237 (15) | −0.0345 (17) |
C38 | 0.095 (2) | 0.0674 (19) | 0.109 (3) | −0.0432 (18) | 0.013 (2) | −0.0102 (19) |
N1 | 0.0498 (11) | 0.0365 (9) | 0.0453 (11) | −0.0181 (9) | −0.0031 (9) | −0.0024 (8) |
N2 | 0.0490 (10) | 0.0440 (10) | 0.0418 (11) | −0.0258 (9) | 0.0026 (8) | −0.0139 (8) |
O1 | 0.0771 (12) | 0.0638 (11) | 0.0718 (13) | −0.0420 (10) | 0.0255 (10) | −0.0241 (10) |
O2 | 0.0664 (11) | 0.0601 (11) | 0.0746 (13) | −0.0291 (9) | 0.0227 (10) | −0.0336 (10) |
S1 | 0.0687 (4) | 0.0355 (3) | 0.0552 (4) | −0.0152 (3) | 0.0100 (3) | −0.0049 (3) |
S2 | 0.0700 (4) | 0.0366 (3) | 0.0557 (4) | −0.0186 (3) | 0.0126 (3) | −0.0027 (3) |
S3 | 0.0593 (4) | 0.0405 (3) | 0.0521 (4) | −0.0215 (3) | 0.0061 (3) | −0.0057 (3) |
S4 | 0.0749 (4) | 0.0411 (3) | 0.0591 (4) | −0.0287 (3) | 0.0121 (3) | −0.0113 (3) |
S5 | 0.0528 (4) | 0.0558 (4) | 0.0887 (6) | −0.0200 (3) | 0.0244 (4) | −0.0157 (4) |
S6 | 0.0604 (4) | 0.0621 (4) | 0.0538 (4) | −0.0315 (3) | 0.0010 (3) | 0.0035 (3) |
S7 | 0.0670 (4) | 0.0736 (4) | 0.0572 (4) | −0.0491 (4) | 0.0194 (3) | −0.0360 (3) |
S8 | 0.0544 (3) | 0.0618 (4) | 0.0499 (4) | −0.0379 (3) | 0.0061 (3) | −0.0210 (3) |
S9 | 0.0609 (4) | 0.0521 (3) | 0.0512 (4) | −0.0329 (3) | 0.0092 (3) | −0.0189 (3) |
S10 | 0.0519 (3) | 0.0606 (4) | 0.0514 (4) | −0.0319 (3) | 0.0066 (3) | −0.0203 (3) |
S11 | 0.0609 (4) | 0.0493 (3) | 0.0573 (4) | −0.0143 (3) | 0.0073 (3) | −0.0237 (3) |
S12 | 0.0493 (3) | 0.0661 (4) | 0.0737 (5) | −0.0261 (3) | 0.0183 (3) | −0.0237 (4) |
C1—O1 | 1.404 (3) | C20—O2 | 1.416 (3) |
C1—H1A | 0.9600 | C20—H20A | 0.9600 |
C1—H1B | 0.9600 | C20—H20B | 0.9600 |
C1—H1C | 0.9600 | C20—H20C | 0.9600 |
C2—O1 | 1.365 (3) | C21—O2 | 1.368 (3) |
C2—C7 | 1.377 (4) | C21—C22 | 1.376 (3) |
C2—C3 | 1.386 (4) | C21—C26 | 1.379 (3) |
C3—C4 | 1.375 (4) | C22—C23 | 1.385 (3) |
C3—H3 | 0.9300 | C22—H22 | 0.9300 |
C4—C5 | 1.379 (3) | C23—C24 | 1.379 (3) |
C4—H4 | 0.9300 | C23—H23 | 0.9300 |
C5—C6 | 1.380 (3) | C24—C25 | 1.387 (3) |
C5—N1 | 1.424 (3) | C24—N2 | 1.431 (3) |
C6—C7 | 1.382 (4) | C25—C26 | 1.380 (3) |
C6—H6 | 0.9300 | C25—H25 | 0.9300 |
C7—H7 | 0.9300 | C26—H26 | 0.9300 |
C8—C9 | 1.357 (3) | C27—C28 | 1.359 (3) |
C8—N1 | 1.383 (3) | C27—N2 | 1.379 (3) |
C8—H8 | 0.9300 | C27—H27 | 0.9300 |
C9—C10 | 1.413 (3) | C28—C29 | 1.413 (3) |
C9—S1 | 1.748 (2) | C28—S7 | 1.740 (2) |
C10—C11 | 1.357 (3) | C29—C30 | 1.360 (3) |
C10—S2 | 1.741 (2) | C29—S8 | 1.747 (2) |
C11—N1 | 1.381 (3) | C30—N2 | 1.381 (3) |
C11—H11 | 0.9300 | C30—H30 | 0.9300 |
C12—C13 | 1.333 (3) | C31—C32 | 1.338 (3) |
C12—S2 | 1.766 (2) | C31—S8 | 1.763 (2) |
C12—S1 | 1.768 (2) | C31—S7 | 1.769 (2) |
C13—S4 | 1.759 (2) | C32—S9 | 1.756 (2) |
C13—S3 | 1.761 (2) | C32—S10 | 1.759 (2) |
C14—C17 | 1.341 (3) | C33—C36 | 1.339 (3) |
C14—S5 | 1.741 (3) | C33—S11 | 1.751 (2) |
C14—S3 | 1.767 (2) | C33—S9 | 1.758 (2) |
C15—C16 | 1.504 (4) | C34—C35 | 1.498 (4) |
C15—S5 | 1.816 (3) | C34—S11 | 1.812 (3) |
C15—H15A | 0.9700 | C34—H34A | 0.9700 |
C15—H15B | 0.9700 | C34—H34B | 0.9700 |
C16—H16A | 0.9600 | C35—H35A | 0.9600 |
C16—H16B | 0.9600 | C35—H35B | 0.9600 |
C16—H16C | 0.9600 | C35—H35C | 0.9600 |
C17—S4 | 1.749 (3) | C36—S12 | 1.744 (2) |
C17—S6 | 1.756 (2) | C36—S10 | 1.764 (3) |
C18—C19 | 1.471 (4) | C37—C38 | 1.497 (4) |
C18—S6 | 1.801 (3) | C37—S12 | 1.803 (3) |
C18—H18A | 0.9700 | C37—H37A | 0.9700 |
C18—H18B | 0.9700 | C37—H37B | 0.9700 |
C19—H19A | 0.9600 | C38—H38A | 0.9600 |
C19—H19B | 0.9600 | C38—H38B | 0.9600 |
C19—H19C | 0.9600 | C38—H38C | 0.9600 |
O1—C1—H1A | 109.5 | C21—C22—H22 | 120.2 |
O1—C1—H1B | 109.5 | C23—C22—H22 | 120.2 |
H1A—C1—H1B | 109.5 | C24—C23—C22 | 121.1 (2) |
O1—C1—H1C | 109.5 | C24—C23—H23 | 119.5 |
H1A—C1—H1C | 109.5 | C22—C23—H23 | 119.5 |
H1B—C1—H1C | 109.5 | C23—C24—C25 | 118.9 (2) |
O1—C2—C7 | 125.3 (2) | C23—C24—N2 | 120.9 (2) |
O1—C2—C3 | 115.5 (2) | C25—C24—N2 | 120.2 (2) |
C7—C2—C3 | 119.1 (2) | C26—C25—C24 | 120.0 (2) |
C4—C3—C2 | 120.7 (2) | C26—C25—H25 | 120.0 |
C4—C3—H3 | 119.6 | C24—C25—H25 | 120.0 |
C2—C3—H3 | 119.6 | C21—C26—C25 | 120.7 (2) |
C3—C4—C5 | 120.2 (2) | C21—C26—H26 | 119.6 |
C3—C4—H4 | 119.9 | C25—C26—H26 | 119.6 |
C5—C4—H4 | 119.9 | C28—C27—N2 | 107.7 (2) |
C4—C5—C6 | 119.1 (2) | C28—C27—H27 | 126.2 |
C4—C5—N1 | 120.0 (2) | N2—C27—H27 | 126.2 |
C6—C5—N1 | 120.9 (2) | C27—C28—C29 | 108.0 (2) |
C5—C6—C7 | 120.9 (2) | C27—C28—S7 | 134.67 (19) |
C5—C6—H6 | 119.6 | C29—C28—S7 | 117.37 (18) |
C7—C6—H6 | 119.6 | C30—C29—C28 | 107.7 (2) |
C2—C7—C6 | 119.9 (2) | C30—C29—S8 | 135.34 (19) |
C2—C7—H7 | 120.0 | C28—C29—S8 | 116.94 (18) |
C6—C7—H7 | 120.0 | C29—C30—N2 | 107.7 (2) |
C9—C8—N1 | 107.5 (2) | C29—C30—H30 | 126.1 |
C9—C8—H8 | 126.2 | N2—C30—H30 | 126.1 |
N1—C8—H8 | 126.2 | C32—C31—S8 | 123.12 (18) |
C8—C9—C10 | 108.2 (2) | C32—C31—S7 | 120.17 (19) |
C8—C9—S1 | 134.61 (18) | S8—C31—S7 | 116.59 (13) |
C10—C9—S1 | 117.11 (18) | C31—C32—S9 | 122.41 (18) |
C11—C10—C9 | 107.6 (2) | C31—C32—S10 | 123.97 (19) |
C11—C10—S2 | 134.99 (18) | S9—C32—S10 | 113.36 (13) |
C9—C10—S2 | 117.30 (18) | C36—C33—S11 | 126.19 (19) |
C10—C11—N1 | 107.9 (2) | C36—C33—S9 | 117.20 (19) |
C10—C11—H11 | 126.0 | S11—C33—S9 | 116.18 (15) |
N1—C11—H11 | 126.0 | C35—C34—S11 | 112.9 (2) |
C13—C12—S2 | 120.85 (18) | C35—C34—H34A | 109.0 |
C13—C12—S1 | 122.40 (18) | S11—C34—H34A | 109.0 |
S2—C12—S1 | 116.69 (13) | C35—C34—H34B | 109.0 |
C12—C13—S4 | 121.99 (18) | S11—C34—H34B | 109.0 |
C12—C13—S3 | 124.17 (18) | H34A—C34—H34B | 107.8 |
S4—C13—S3 | 113.72 (14) | C34—C35—H35A | 109.5 |
C17—C14—S5 | 125.62 (19) | C34—C35—H35B | 109.5 |
C17—C14—S3 | 116.62 (19) | H35A—C35—H35B | 109.5 |
S5—C14—S3 | 117.63 (14) | C34—C35—H35C | 109.5 |
C16—C15—S5 | 114.7 (2) | H35A—C35—H35C | 109.5 |
C16—C15—H15A | 108.6 | H35B—C35—H35C | 109.5 |
S5—C15—H15A | 108.6 | C33—C36—S12 | 124.2 (2) |
C16—C15—H15B | 108.6 | C33—C36—S10 | 116.78 (18) |
S5—C15—H15B | 108.6 | S12—C36—S10 | 118.41 (15) |
H15A—C15—H15B | 107.6 | C38—C37—S12 | 114.2 (2) |
C15—C16—H16A | 109.5 | C38—C37—H37A | 108.7 |
C15—C16—H16B | 109.5 | S12—C37—H37A | 108.7 |
H16A—C16—H16B | 109.5 | C38—C37—H37B | 108.7 |
C15—C16—H16C | 109.5 | S12—C37—H37B | 108.7 |
H16A—C16—H16C | 109.5 | H37A—C37—H37B | 107.6 |
H16B—C16—H16C | 109.5 | C37—C38—H38A | 109.5 |
C14—C17—S4 | 117.72 (19) | C37—C38—H38B | 109.5 |
C14—C17—S6 | 127.2 (2) | H38A—C38—H38B | 109.5 |
S4—C17—S6 | 115.09 (14) | C37—C38—H38C | 109.5 |
C19—C18—S6 | 110.6 (3) | H38A—C38—H38C | 109.5 |
C19—C18—H18A | 109.5 | H38B—C38—H38C | 109.5 |
S6—C18—H18A | 109.5 | C11—N1—C8 | 108.78 (19) |
C19—C18—H18B | 109.5 | C11—N1—C5 | 125.79 (19) |
S6—C18—H18B | 109.5 | C8—N1—C5 | 125.38 (19) |
H18A—C18—H18B | 108.1 | C27—N2—C30 | 108.90 (19) |
C18—C19—H19A | 109.5 | C27—N2—C24 | 124.90 (19) |
C18—C19—H19B | 109.5 | C30—N2—C24 | 126.1 (2) |
H19A—C19—H19B | 109.5 | C2—O1—C1 | 118.4 (2) |
C18—C19—H19C | 109.5 | C21—O2—C20 | 118.4 (2) |
H19A—C19—H19C | 109.5 | C9—S1—C12 | 94.27 (11) |
H19B—C19—H19C | 109.5 | C10—S2—C12 | 94.50 (11) |
O2—C20—H20A | 109.5 | C13—S3—C14 | 95.12 (12) |
O2—C20—H20B | 109.5 | C17—S4—C13 | 95.40 (11) |
H20A—C20—H20B | 109.5 | C14—S5—C15 | 100.98 (12) |
O2—C20—H20C | 109.5 | C17—S6—C18 | 102.71 (14) |
H20A—C20—H20C | 109.5 | C28—S7—C31 | 94.32 (11) |
H20B—C20—H20C | 109.5 | C29—S8—C31 | 94.39 (11) |
O2—C21—C22 | 124.5 (2) | C32—S9—C33 | 95.30 (12) |
O2—C21—C26 | 115.8 (2) | C32—S10—C36 | 95.20 (12) |
C22—C21—C26 | 119.7 (2) | C33—S11—C34 | 101.04 (12) |
C21—C22—C23 | 119.7 (2) | C36—S12—C37 | 101.95 (12) |
Experimental details
Crystal data | |
Chemical formula | C19H19NOS6 |
Mr | 469.71 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 291 |
a, b, c (Å) | 11.974 (2), 12.121 (2), 16.762 (3) |
α, β, γ (°) | 73.90 (3), 85.53 (3), 65.43 (3) |
V (Å3) | 2123.8 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.65 |
Crystal size (mm) | 0.14 × 0.13 × 0.12 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.914, 0.926 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21057, 9633, 6504 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.117, 1.01 |
No. of reflections | 9633 |
No. of parameters | 493 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.31, −0.27 |
Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).
Acknowledgements
The authors acknowledge financial support from the National Natural Science Foundation of China (grant No. 20662010), the Specialized Research Fund for the Doctoral Programm of Higher Education (grant No. 2006184001) and the Open Project of the State Key Laboratory of Supramolecular Structure and Materials, Jilin University.
References
Becher, J., Nielsen, K. & Jeppesen, J. O. (2004). J. Phys. IV Fr. 114, 445–448. Web of Science CrossRef CAS Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yin, B. Z., Yang, Y. H., Cong, Z. Q. & Imafuku, K. (2004). Heterocycles, 63, 1577–1584. CAS Google Scholar
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Pyrrolo-tetrathiafulvalene derivatives, an important class of electron-donors, are versatile building blocks in supramolecular and materials chemistry (Becher et al., 2004). Recently, we have reported the synthesis and eletron donor properties of the title compound, N-(4-methoxyphenyl)pyrrolo[3,4-d] tetrathiafulvalene (Yin et al., 2004). In this paper, we report its crystal structure.
The asymmetric unit of the title compound contains two independent molecules (Fig. 1), M1 and M2, respectively. The tetrathiafulvalene and benzene ring are nearly coplanar in both M1 and M2 molecules. Conformations of ethyl groups in M1 and M2 are different: two ethyls in M1 lie in the different side of the plane, while at the same side in M2. In the absence of short intermolecular contacts, the crystal packing is featured by packing of enlongated molecules parallel to direction [10-1].