organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

(Received 22 October 2009; accepted 10 November 2009; online 14 November 2009)

The asymmetric unit of the title compound, C19H19NOS6, 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[\overline{1}]].

Related literature

For general background to the use of pyrrolo-tetra­thia­fulvalene derivatives as building blocks in supra­molecular and materials chemistry, see Becher et al. (2004[Becher, J., Nielsen, K. & Jeppesen, J. O. (2004). J. Phys. IV Fr. 114, 445-448.]). For details of the synthesis, see Yin et al. (2004[Yin, B. Z., Yang, Y. H., Cong, Z. Q. & Imafuku, K. (2004). Heterocycles, 63, 1577-1584.]).

[Scheme 1]

Experimental

Crystal data
  • C19H19NOS6

  • Mr = 469.71

  • Triclinic, [P \overline 1]

  • a = 11.974 (2) Å

  • b = 12.121 (2) Å

  • c = 16.762 (3) Å

  • α = 73.90 (3)°

  • β = 85.53 (3)°

  • γ = 65.43 (3)°

  • V = 2123.8 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.65 mm−1

  • T = 291 K

  • 0.14 × 0.13 × 0.12 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.914, Tmax = 0.926

  • 21057 measured reflections

  • 9633 independent reflections

  • 6504 reflections with I > 2σ(I)

  • Rint = 0.033

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.117

  • S = 1.01

  • 9633 reflections

  • 493 parameters

  • H-atom parameters constrained

  • Δρmax = 0.31 e Å−3

  • Δρmin = −0.27 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998[Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002[Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

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].

Related literature top

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 top

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.

Refinement top

C-bound H-atoms were placed in calculated positions (C—H 0.93-0.97 Å), and were included in the refinement in the riding model, with Uiso(H) = 1.5 or 1.2 Ueq(C).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. Two independent molecules of the title compound, with the atom numbering and 30% probalility displacement ellipsoids.
2-[4,5-Bis(ethylsulfanyl)-1,3-dithiol-2-ylidene]-5-(4-methoxyphenyl)- 5H-1,3-dithiolo[4,5-c]pyrrole top
Crystal data top
C19H19NOS6Z = 4
Mr = 469.71F(000) = 976
Triclinic, P1Dx = 1.469 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.974 (2) ÅCell parameters from 14243 reflections
b = 12.121 (2) Åθ = 3.1–27.5°
c = 16.762 (3) ŵ = 0.65 mm1
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
Data collection top
Rigaku R-AXIS RAPID
diffractometer
9633 independent reflections
Radiation source: fine-focus sealed tube6504 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
ω scansθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1513
Tmin = 0.914, Tmax = 0.926k = 1515
21057 measured reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-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 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.27 e Å3
Crystal data top
C19H19NOS6γ = 65.43 (3)°
Mr = 469.71V = 2123.8 (7) Å3
Triclinic, P1Z = 4
a = 11.974 (2) ÅMo Kα radiation
b = 12.121 (2) ŵ = 0.65 mm1
c = 16.762 (3) ÅT = 291 K
α = 73.90 (3)°0.14 × 0.13 × 0.12 mm
β = 85.53 (3)°
Data collection top
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 = 0.926Rint = 0.033
21057 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.117H-atom parameters constrained
S = 1.01Δρmax = 0.31 e Å3
9633 reflectionsΔρmin = 0.27 e Å3
493 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.0187 (3)0.4802 (3)0.7889 (2)0.0854 (10)
H1A0.07260.51200.80440.128*
H1B0.03880.47590.83160.128*
H1C0.02520.53540.73760.128*
C20.1669 (2)0.3475 (2)0.71499 (16)0.0515 (6)
C30.2258 (2)0.2272 (2)0.70449 (18)0.0602 (7)
H30.20790.16220.73860.072*
C40.3105 (2)0.2030 (2)0.64426 (17)0.0571 (7)
H40.34940.12190.63780.069*
C50.3380 (2)0.2985 (2)0.59338 (15)0.0442 (5)
C60.2771 (2)0.4189 (2)0.60244 (16)0.0548 (6)
H60.29390.48410.56760.066*
C70.1915 (2)0.4437 (2)0.66262 (17)0.0563 (7)
H70.15050.52540.66780.068*
C80.5125 (2)0.1538 (2)0.52980 (15)0.0486 (6)
H80.51880.07760.56590.058*
C90.5849 (2)0.1689 (2)0.46494 (14)0.0442 (5)
C100.5441 (2)0.2991 (2)0.42581 (14)0.0446 (5)
C110.4482 (2)0.3611 (2)0.46830 (15)0.0476 (6)
H110.40410.44800.45640.057*
C120.7299 (2)0.1887 (2)0.34512 (14)0.0430 (5)
C130.8184 (2)0.1662 (2)0.29066 (15)0.0444 (5)
C140.9907 (2)0.0657 (2)0.19511 (15)0.0469 (6)
C151.0237 (3)0.1466 (2)0.1501 (2)0.0684 (8)
H15A1.07820.21490.12750.082*
H15B1.00680.18370.20630.082*
C160.9051 (3)0.0780 (3)0.09887 (18)0.0773 (9)
H16A0.84850.01340.12260.116*
H16B0.87050.13640.09810.116*
H16C0.92050.04050.04310.116*
C170.9521 (2)0.1906 (2)0.16305 (15)0.0485 (6)
C181.1509 (3)0.2438 (3)0.0997 (2)0.0904 (12)
H18A1.14880.26780.15060.109*
H18B1.20490.15510.10990.109*
C191.1992 (3)0.3184 (4)0.0333 (3)0.1182 (16)
H19A1.21850.28240.01300.177*
H19B1.27210.31780.05380.177*
H19C1.13840.40350.01580.177*
C200.5385 (3)0.8748 (3)0.7996 (2)0.0770 (9)
H20A0.58210.88340.75110.116*
H20B0.59590.91510.83680.116*
H20C0.49410.78710.82700.116*
C210.3663 (2)0.8889 (2)0.72209 (15)0.0460 (5)
C220.3512 (2)0.7916 (2)0.68927 (16)0.0537 (6)
H220.40390.75100.70290.064*
C230.2572 (2)0.7543 (2)0.63580 (17)0.0535 (6)
H230.24670.68800.61420.064*
C240.17888 (19)0.8141 (2)0.61409 (13)0.0402 (5)
C250.1954 (2)0.9128 (2)0.64690 (15)0.0469 (5)
H250.14380.95460.63250.056*
C260.2882 (2)0.9490 (2)0.70089 (16)0.0517 (6)
H260.29831.01460.72320.062*
C270.0765 (2)0.7044 (2)0.50572 (14)0.0450 (5)
H270.13220.67060.50180.054*
C280.0251 (2)0.6924 (2)0.46045 (14)0.0424 (5)
C290.0835 (2)0.7582 (2)0.48538 (14)0.0414 (5)
C300.0163 (2)0.8089 (2)0.54558 (15)0.0448 (5)
H300.03360.85730.57310.054*
C310.21143 (19)0.6709 (2)0.36860 (14)0.0403 (5)
C320.2935 (2)0.6418 (2)0.31059 (14)0.0408 (5)
C330.4041 (2)0.5729 (2)0.18181 (14)0.0435 (5)
C340.3035 (2)0.5950 (3)0.03313 (16)0.0587 (7)
H34A0.30660.55580.01070.070*
H34B0.23170.59710.06480.070*
C350.2904 (3)0.7273 (3)0.00531 (19)0.0732 (9)
H35A0.28250.76830.03760.110*
H35B0.21850.77240.04190.110*
H35C0.36160.72590.03620.110*
C360.4630 (2)0.6343 (2)0.20262 (15)0.0450 (5)
C370.5531 (3)0.8156 (3)0.1410 (2)0.0684 (8)
H37A0.54030.83070.19550.082*
H37B0.62280.83340.11840.082*
C380.4416 (3)0.9048 (3)0.0860 (2)0.0906 (11)
H38A0.45010.88560.03340.136*
H38B0.43310.98960.07760.136*
H38C0.37010.89640.11180.136*
N10.42782 (17)0.27241 (16)0.53236 (12)0.0454 (5)
N20.08223 (16)0.77573 (17)0.55855 (11)0.0421 (4)
O10.08803 (17)0.35935 (18)0.77861 (12)0.0664 (5)
O20.45483 (16)0.93211 (17)0.77612 (12)0.0638 (5)
S10.71479 (6)0.06700 (5)0.42617 (4)0.05735 (19)
S20.62565 (6)0.34433 (6)0.34207 (4)0.05800 (19)
S30.92856 (6)0.01481 (5)0.29013 (4)0.05201 (17)
S40.84103 (7)0.28873 (6)0.21607 (4)0.05770 (18)
S51.10304 (6)0.04916 (7)0.15474 (5)0.0687 (2)
S60.99851 (6)0.26916 (7)0.07115 (4)0.06066 (19)
S70.09330 (6)0.61643 (7)0.38385 (4)0.05587 (17)
S80.21920 (5)0.75478 (6)0.43717 (4)0.04944 (16)
S90.29160 (6)0.54706 (6)0.24866 (4)0.05071 (16)
S100.42090 (5)0.68105 (6)0.29521 (4)0.05067 (16)
S110.43992 (6)0.49999 (6)0.10086 (4)0.05701 (18)
S120.59037 (6)0.65155 (7)0.15249 (5)0.06202 (19)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.097 (2)0.081 (2)0.105 (3)0.0512 (19)0.042 (2)0.051 (2)
C20.0554 (14)0.0509 (13)0.0568 (15)0.0296 (12)0.0023 (12)0.0155 (12)
C30.0663 (16)0.0521 (14)0.0682 (18)0.0355 (13)0.0141 (13)0.0110 (13)
C40.0640 (15)0.0417 (13)0.0671 (17)0.0263 (12)0.0062 (13)0.0106 (12)
C50.0444 (12)0.0428 (12)0.0471 (13)0.0218 (10)0.0045 (10)0.0069 (10)
C60.0663 (16)0.0430 (13)0.0565 (16)0.0290 (12)0.0068 (12)0.0063 (11)
C70.0628 (15)0.0441 (13)0.0652 (17)0.0250 (12)0.0078 (13)0.0163 (12)
C80.0563 (14)0.0358 (11)0.0489 (14)0.0186 (11)0.0008 (11)0.0040 (10)
C90.0487 (12)0.0357 (11)0.0456 (13)0.0168 (10)0.0052 (10)0.0059 (10)
C100.0519 (13)0.0376 (11)0.0430 (13)0.0217 (10)0.0054 (10)0.0017 (10)
C110.0511 (13)0.0357 (11)0.0506 (14)0.0172 (10)0.0017 (11)0.0034 (10)
C120.0507 (12)0.0396 (11)0.0398 (12)0.0202 (10)0.0027 (10)0.0083 (9)
C130.0537 (13)0.0408 (11)0.0429 (13)0.0234 (10)0.0028 (10)0.0102 (10)
C140.0464 (12)0.0482 (13)0.0483 (14)0.0248 (11)0.0054 (10)0.0088 (11)
C150.0791 (18)0.0409 (13)0.081 (2)0.0226 (13)0.0314 (16)0.0208 (13)
C160.108 (2)0.079 (2)0.0578 (19)0.0528 (19)0.0120 (17)0.0171 (16)
C170.0498 (13)0.0501 (13)0.0482 (14)0.0272 (11)0.0007 (10)0.0064 (11)
C180.0609 (18)0.090 (2)0.104 (3)0.0400 (17)0.0002 (17)0.012 (2)
C190.091 (2)0.121 (3)0.145 (4)0.071 (2)0.028 (2)0.001 (3)
C200.0716 (18)0.076 (2)0.090 (2)0.0347 (16)0.0337 (17)0.0331 (18)
C210.0497 (13)0.0392 (11)0.0452 (13)0.0149 (10)0.0014 (10)0.0109 (10)
C220.0571 (14)0.0534 (14)0.0618 (17)0.0319 (12)0.0115 (12)0.0207 (12)
C230.0632 (15)0.0511 (13)0.0640 (17)0.0353 (12)0.0140 (12)0.0270 (12)
C240.0464 (12)0.0398 (11)0.0371 (12)0.0201 (10)0.0018 (9)0.0096 (9)
C250.0566 (13)0.0463 (12)0.0486 (14)0.0304 (11)0.0012 (11)0.0143 (11)
C260.0631 (15)0.0442 (12)0.0562 (16)0.0250 (12)0.0028 (12)0.0218 (11)
C270.0539 (13)0.0515 (13)0.0463 (13)0.0345 (11)0.0056 (10)0.0188 (11)
C280.0517 (13)0.0451 (12)0.0401 (12)0.0282 (11)0.0034 (10)0.0136 (10)
C290.0483 (12)0.0445 (12)0.0380 (12)0.0263 (10)0.0039 (9)0.0079 (10)
C300.0511 (13)0.0500 (13)0.0487 (14)0.0316 (11)0.0014 (10)0.0192 (11)
C310.0440 (12)0.0385 (11)0.0403 (12)0.0202 (10)0.0037 (9)0.0068 (9)
C320.0454 (12)0.0389 (11)0.0388 (12)0.0190 (10)0.0021 (9)0.0078 (9)
C330.0435 (12)0.0371 (11)0.0421 (13)0.0107 (10)0.0009 (9)0.0076 (9)
C340.0603 (15)0.0762 (18)0.0533 (16)0.0344 (14)0.0063 (12)0.0293 (14)
C350.0787 (19)0.0650 (18)0.0669 (19)0.0230 (16)0.0143 (15)0.0098 (15)
C360.0445 (12)0.0421 (12)0.0453 (13)0.0165 (10)0.0035 (10)0.0095 (10)
C370.0676 (17)0.0814 (19)0.081 (2)0.0502 (16)0.0237 (15)0.0345 (17)
C380.095 (2)0.0674 (19)0.109 (3)0.0432 (18)0.013 (2)0.0102 (19)
N10.0498 (11)0.0365 (9)0.0453 (11)0.0181 (9)0.0031 (9)0.0024 (8)
N20.0490 (10)0.0440 (10)0.0418 (11)0.0258 (9)0.0026 (8)0.0139 (8)
O10.0771 (12)0.0638 (11)0.0718 (13)0.0420 (10)0.0255 (10)0.0241 (10)
O20.0664 (11)0.0601 (11)0.0746 (13)0.0291 (9)0.0227 (10)0.0336 (10)
S10.0687 (4)0.0355 (3)0.0552 (4)0.0152 (3)0.0100 (3)0.0049 (3)
S20.0700 (4)0.0366 (3)0.0557 (4)0.0186 (3)0.0126 (3)0.0027 (3)
S30.0593 (4)0.0405 (3)0.0521 (4)0.0215 (3)0.0061 (3)0.0057 (3)
S40.0749 (4)0.0411 (3)0.0591 (4)0.0287 (3)0.0121 (3)0.0113 (3)
S50.0528 (4)0.0558 (4)0.0887 (6)0.0200 (3)0.0244 (4)0.0157 (4)
S60.0604 (4)0.0621 (4)0.0538 (4)0.0315 (3)0.0010 (3)0.0035 (3)
S70.0670 (4)0.0736 (4)0.0572 (4)0.0491 (4)0.0194 (3)0.0360 (3)
S80.0544 (3)0.0618 (4)0.0499 (4)0.0379 (3)0.0061 (3)0.0210 (3)
S90.0609 (4)0.0521 (3)0.0512 (4)0.0329 (3)0.0092 (3)0.0189 (3)
S100.0519 (3)0.0606 (4)0.0514 (4)0.0319 (3)0.0066 (3)0.0203 (3)
S110.0609 (4)0.0493 (3)0.0573 (4)0.0143 (3)0.0073 (3)0.0237 (3)
S120.0493 (3)0.0661 (4)0.0737 (5)0.0261 (3)0.0183 (3)0.0237 (4)
Geometric parameters (Å, º) top
C1—O11.404 (3)C20—O21.416 (3)
C1—H1A0.9600C20—H20A0.9600
C1—H1B0.9600C20—H20B0.9600
C1—H1C0.9600C20—H20C0.9600
C2—O11.365 (3)C21—O21.368 (3)
C2—C71.377 (4)C21—C221.376 (3)
C2—C31.386 (4)C21—C261.379 (3)
C3—C41.375 (4)C22—C231.385 (3)
C3—H30.9300C22—H220.9300
C4—C51.379 (3)C23—C241.379 (3)
C4—H40.9300C23—H230.9300
C5—C61.380 (3)C24—C251.387 (3)
C5—N11.424 (3)C24—N21.431 (3)
C6—C71.382 (4)C25—C261.380 (3)
C6—H60.9300C25—H250.9300
C7—H70.9300C26—H260.9300
C8—C91.357 (3)C27—C281.359 (3)
C8—N11.383 (3)C27—N21.379 (3)
C8—H80.9300C27—H270.9300
C9—C101.413 (3)C28—C291.413 (3)
C9—S11.748 (2)C28—S71.740 (2)
C10—C111.357 (3)C29—C301.360 (3)
C10—S21.741 (2)C29—S81.747 (2)
C11—N11.381 (3)C30—N21.381 (3)
C11—H110.9300C30—H300.9300
C12—C131.333 (3)C31—C321.338 (3)
C12—S21.766 (2)C31—S81.763 (2)
C12—S11.768 (2)C31—S71.769 (2)
C13—S41.759 (2)C32—S91.756 (2)
C13—S31.761 (2)C32—S101.759 (2)
C14—C171.341 (3)C33—C361.339 (3)
C14—S51.741 (3)C33—S111.751 (2)
C14—S31.767 (2)C33—S91.758 (2)
C15—C161.504 (4)C34—C351.498 (4)
C15—S51.816 (3)C34—S111.812 (3)
C15—H15A0.9700C34—H34A0.9700
C15—H15B0.9700C34—H34B0.9700
C16—H16A0.9600C35—H35A0.9600
C16—H16B0.9600C35—H35B0.9600
C16—H16C0.9600C35—H35C0.9600
C17—S41.749 (3)C36—S121.744 (2)
C17—S61.756 (2)C36—S101.764 (3)
C18—C191.471 (4)C37—C381.497 (4)
C18—S61.801 (3)C37—S121.803 (3)
C18—H18A0.9700C37—H37A0.9700
C18—H18B0.9700C37—H37B0.9700
C19—H19A0.9600C38—H38A0.9600
C19—H19B0.9600C38—H38B0.9600
C19—H19C0.9600C38—H38C0.9600
O1—C1—H1A109.5C21—C22—H22120.2
O1—C1—H1B109.5C23—C22—H22120.2
H1A—C1—H1B109.5C24—C23—C22121.1 (2)
O1—C1—H1C109.5C24—C23—H23119.5
H1A—C1—H1C109.5C22—C23—H23119.5
H1B—C1—H1C109.5C23—C24—C25118.9 (2)
O1—C2—C7125.3 (2)C23—C24—N2120.9 (2)
O1—C2—C3115.5 (2)C25—C24—N2120.2 (2)
C7—C2—C3119.1 (2)C26—C25—C24120.0 (2)
C4—C3—C2120.7 (2)C26—C25—H25120.0
C4—C3—H3119.6C24—C25—H25120.0
C2—C3—H3119.6C21—C26—C25120.7 (2)
C3—C4—C5120.2 (2)C21—C26—H26119.6
C3—C4—H4119.9C25—C26—H26119.6
C5—C4—H4119.9C28—C27—N2107.7 (2)
C4—C5—C6119.1 (2)C28—C27—H27126.2
C4—C5—N1120.0 (2)N2—C27—H27126.2
C6—C5—N1120.9 (2)C27—C28—C29108.0 (2)
C5—C6—C7120.9 (2)C27—C28—S7134.67 (19)
C5—C6—H6119.6C29—C28—S7117.37 (18)
C7—C6—H6119.6C30—C29—C28107.7 (2)
C2—C7—C6119.9 (2)C30—C29—S8135.34 (19)
C2—C7—H7120.0C28—C29—S8116.94 (18)
C6—C7—H7120.0C29—C30—N2107.7 (2)
C9—C8—N1107.5 (2)C29—C30—H30126.1
C9—C8—H8126.2N2—C30—H30126.1
N1—C8—H8126.2C32—C31—S8123.12 (18)
C8—C9—C10108.2 (2)C32—C31—S7120.17 (19)
C8—C9—S1134.61 (18)S8—C31—S7116.59 (13)
C10—C9—S1117.11 (18)C31—C32—S9122.41 (18)
C11—C10—C9107.6 (2)C31—C32—S10123.97 (19)
C11—C10—S2134.99 (18)S9—C32—S10113.36 (13)
C9—C10—S2117.30 (18)C36—C33—S11126.19 (19)
C10—C11—N1107.9 (2)C36—C33—S9117.20 (19)
C10—C11—H11126.0S11—C33—S9116.18 (15)
N1—C11—H11126.0C35—C34—S11112.9 (2)
C13—C12—S2120.85 (18)C35—C34—H34A109.0
C13—C12—S1122.40 (18)S11—C34—H34A109.0
S2—C12—S1116.69 (13)C35—C34—H34B109.0
C12—C13—S4121.99 (18)S11—C34—H34B109.0
C12—C13—S3124.17 (18)H34A—C34—H34B107.8
S4—C13—S3113.72 (14)C34—C35—H35A109.5
C17—C14—S5125.62 (19)C34—C35—H35B109.5
C17—C14—S3116.62 (19)H35A—C35—H35B109.5
S5—C14—S3117.63 (14)C34—C35—H35C109.5
C16—C15—S5114.7 (2)H35A—C35—H35C109.5
C16—C15—H15A108.6H35B—C35—H35C109.5
S5—C15—H15A108.6C33—C36—S12124.2 (2)
C16—C15—H15B108.6C33—C36—S10116.78 (18)
S5—C15—H15B108.6S12—C36—S10118.41 (15)
H15A—C15—H15B107.6C38—C37—S12114.2 (2)
C15—C16—H16A109.5C38—C37—H37A108.7
C15—C16—H16B109.5S12—C37—H37A108.7
H16A—C16—H16B109.5C38—C37—H37B108.7
C15—C16—H16C109.5S12—C37—H37B108.7
H16A—C16—H16C109.5H37A—C37—H37B107.6
H16B—C16—H16C109.5C37—C38—H38A109.5
C14—C17—S4117.72 (19)C37—C38—H38B109.5
C14—C17—S6127.2 (2)H38A—C38—H38B109.5
S4—C17—S6115.09 (14)C37—C38—H38C109.5
C19—C18—S6110.6 (3)H38A—C38—H38C109.5
C19—C18—H18A109.5H38B—C38—H38C109.5
S6—C18—H18A109.5C11—N1—C8108.78 (19)
C19—C18—H18B109.5C11—N1—C5125.79 (19)
S6—C18—H18B109.5C8—N1—C5125.38 (19)
H18A—C18—H18B108.1C27—N2—C30108.90 (19)
C18—C19—H19A109.5C27—N2—C24124.90 (19)
C18—C19—H19B109.5C30—N2—C24126.1 (2)
H19A—C19—H19B109.5C2—O1—C1118.4 (2)
C18—C19—H19C109.5C21—O2—C20118.4 (2)
H19A—C19—H19C109.5C9—S1—C1294.27 (11)
H19B—C19—H19C109.5C10—S2—C1294.50 (11)
O2—C20—H20A109.5C13—S3—C1495.12 (12)
O2—C20—H20B109.5C17—S4—C1395.40 (11)
H20A—C20—H20B109.5C14—S5—C15100.98 (12)
O2—C20—H20C109.5C17—S6—C18102.71 (14)
H20A—C20—H20C109.5C28—S7—C3194.32 (11)
H20B—C20—H20C109.5C29—S8—C3194.39 (11)
O2—C21—C22124.5 (2)C32—S9—C3395.30 (12)
O2—C21—C26115.8 (2)C32—S10—C3695.20 (12)
C22—C21—C26119.7 (2)C33—S11—C34101.04 (12)
C21—C22—C23119.7 (2)C36—S12—C37101.95 (12)

Experimental details

Crystal data
Chemical formulaC19H19NOS6
Mr469.71
Crystal system, space groupTriclinic, 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)
V3)2123.8 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.65
Crystal size (mm)0.14 × 0.13 × 0.12
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.914, 0.926
No. of measured, independent and
observed [I > 2σ(I)] reflections
21057, 9633, 6504
Rint0.033
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.117, 1.01
No. of reflections9633
No. of parameters493
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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

First citationBecher, J., Nielsen, K. & Jeppesen, J. O. (2004). J. Phys. IV Fr. 114, 445–448.  Web of Science CrossRef CAS Google Scholar
First citationHigashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationYin, B. Z., Yang, Y. H., Cong, Z. Q. & Imafuku, K. (2004). Heterocycles, 63, 1577–1584.  CAS Google Scholar

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