Ethyl 2-[4,5-bis­(butyl­sulfan­yl)-1,3-dithiol-2-yl­idene]-1,3-dithiolo[4,5-c]pyrrole-4-carboxyl­ate

Li, D.-F.; Zhu, X.-F.; Guan, S.; Hou, R.-B.

doi:10.1107/S1600536812015309

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1400

doi:10.1107/S1600536812015309

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Ethyl 2-[4,5-bis(butylsulfanyl)-1,3-dithiol-2-ylidene]-1,3-dithiolo[4,5-c]pyrrole-4-carboxylate

Dong-Feng Li,^a Xiao-Fei Zhu,^a Shuang Guan ^a and Rui-Bin Hou ^a ^*

^aSchool of Chemistry and Life Science, Changchun University of Technology, Changchun 130012, People's Republic of China
^*Correspondence e-mail: hrb1018@163.com

(Received 12 March 2012; accepted 7 April 2012; online 18 April 2012)

In the title molecule, C₁₉H₂₅NO₂S₆, the butyl chains are each disordered over two conformations in a 0.689 (10):0.311 (10) ratio. In the crystal, pairs of N—H⋯O hydrogen bonds link molecules into centrosymmetric dimers. Short S⋯S contacts of 3.553 (4) Å are observed.

Related literature

For background to tetrathiafulvalenes, see: Jeppesen et al. (1999 ); Hansel et al. (2004 ). For details of the synthesis, see: Hou et al. (2010 ). For a similar structure, see: Hou & Yin (2010 ).

Experimental

Crystal data

C₁₉H₂₅NO₂S₆
M_r = 491.76
Monoclinic, P 2₁ /c
a = 9.687 (3) Å
b = 26.608 (9) Å
c = 8.876 (5) Å
β = 108.408 (17)°
V = 2170.7 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.65 mm⁻¹
T = 288 K
0.48 × 0.18 × 0.17 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.747, T_max = 0.898
17087 measured reflections
3823 independent reflections
3114 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.120
S = 1.04
3823 reflections
309 parameters
188 restraints
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.71 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	1.96	2.782 (3)	160
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: 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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812015309/cv5262sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812015309/cv5262Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812015309/cv5262Isup3.cml

checkCIF report

Comment top

The tetrathiafulvalenes (TTFs) have attracted considerable attention in organic synthesis (Jeppesen et al., 1999) due to high electrical conductivity and superconductor properties of these compounds. Recently, Hansel reported a series of novel donor-π-acceptor dyads with pyrrolo-annelated tetrathiafulvalene units, which possess significant third-order non-linear optical properties (Hansel et al., 2004). In this paper, we describe the crystal structure of the title compound (I), which is a key precursor of the dyads.

In (I) (Fig. 1), all bond lengths and angles are normal and comparable with the reported ones (Hou & Yin, 2010). Except C11 and two butyls, all non-hydrogen atoms are nearly coplanar. The intermolecular N—H···O hydrogen bonds (Table 1) link the molecuels into dimers, and the dimers are further arranged along [101] direction due to the short S···S [3.553 (4) Å] interactions.

Related literature top

For background to tetrathiafulvalenes, see: Jeppesen et al. (1999); Hansel et al. (2004). For details of the synthesis, see: Hou et al. (2010). For the similar structure, see: Hou & Yin (2010).

Experimental top

The title compound was prepared according to the literature (Hou et al., 2010). Single crystals suitable for X-ray diffraction were prepared by slow evaporation method from a solution in dichloromethane/petroleum (60–90 °C) at room temperature.

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound with displacement ellipsoids drawn at the 30% probalility level. Only major components of the disordered groups are shown.

Ethyl 2-[4,5-bis(butylsulfanyl)-1,3-dithiol-2-ylidene]- 1,3-dithiolo[4,5-c]pyrrole-4-carboxylate top

Crystal data top

C₁₉H₂₅NO₂S₆	F(000) = 1032
M_r = 491.76	D_x = 1.505 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 15498 reflections
a = 9.687 (3) Å	θ = 3.1–27.5°
b = 26.608 (9) Å	µ = 0.65 mm⁻¹
c = 8.876 (5) Å	T = 288 K
β = 108.408 (17)°	Block, yellow
V = 2170.7 (15) Å³	0.48 × 0.18 × 0.17 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	3823 independent reflections
Radiation source: fine-focus sealed tube	3114 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ω scans	θ_max = 25.0°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −11→11
T_min = 0.747, T_max = 0.898	k = −31→31
17087 measured reflections	l = −10→10

Refinement top

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0611P)² + 1.4202P] where P = (F_o² + 2F_c²)/3
3823 reflections	(Δ/σ)_max = 0.001
309 parameters	Δρ_max = 0.39 e Å⁻³
188 restraints	Δρ_min = −0.71 e Å⁻³

Crystal data top

C₁₉H₂₅NO₂S₆	V = 2170.7 (15) Å³
M_r = 491.76	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.687 (3) Å	µ = 0.65 mm⁻¹
b = 26.608 (9) Å	T = 288 K
c = 8.876 (5) Å	0.48 × 0.18 × 0.17 mm
β = 108.408 (17)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3823 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3114 reflections with I > 2σ(I)
T_min = 0.747, T_max = 0.898	R_int = 0.030
17087 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	188 restraints
wR(F²) = 0.120	H-atom parameters constrained
S = 1.04	Δρ_max = 0.39 e Å⁻³
3823 reflections	Δρ_min = −0.71 e Å⁻³
309 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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.4627 (3)	0.46393 (10)	0.2578 (3)	0.0442 (6)
C2	0.3963 (3)	0.45459 (9)	0.3722 (3)	0.0413 (6)
C3	0.2598 (3)	0.47643 (10)	0.3237 (3)	0.0448 (6)
C4	0.2437 (3)	0.49832 (11)	0.1810 (3)	0.0486 (7)
H4	0.1619	0.5157	0.1197	0.058*
C5	0.2830 (3)	0.43726 (10)	0.5907 (3)	0.0437 (6)
C6	0.2589 (3)	0.42284 (10)	0.7241 (3)	0.0460 (6)
C7	0.2628 (4)	0.37832 (11)	0.9810 (3)	0.0491 (7)
C8	0.1321 (3)	0.39944 (11)	0.9317 (3)	0.0491 (7)
C9	0.6006 (3)	0.44958 (11)	0.2450 (3)	0.0474 (7)
C10	0.8040 (4)	0.40090 (14)	0.3572 (5)	0.0669 (9)
H10A	0.8668	0.3919	0.4624	0.080*
H10B	0.8542	0.4251	0.3114	0.080*
C11	0.7626 (7)	0.3553 (2)	0.2540 (8)	0.151 (3)
H11A	0.7100	0.3324	0.2992	0.227*
H11B	0.8489	0.3392	0.2466	0.227*
H11C	0.7024	0.3651	0.1499	0.227*
S6	0.00077 (10)	0.39799 (4)	1.02888 (11)	0.0656 (3)
C12	−0.1593 (4)	0.37886 (14)	0.8701 (5)	0.0757 (10)
H12A	−0.2410	0.3777	0.9110	0.091*	0.689 (10)
H12B	−0.1806	0.4043	0.7876	0.091*	0.689 (10)
H12C	−0.2459	0.3855	0.8995	0.091*	0.311 (10)
H12D	−0.1662	0.3980	0.7749	0.091*	0.311 (10)
C13	−0.1481 (11)	0.3310 (2)	0.7998 (12)	0.079 (2)	0.689 (10)
H13A	−0.1252	0.3055	0.8820	0.095*	0.689 (10)
H13B	−0.0684	0.3322	0.7557	0.095*	0.689 (10)
C14	−0.2837 (10)	0.3163 (3)	0.6721 (11)	0.084 (2)	0.689 (10)
H14A	−0.3045	0.3393	0.5830	0.101*	0.689 (10)
H14B	−0.3662	0.3155	0.7117	0.101*	0.689 (10)
C15	−0.249 (2)	0.2639 (4)	0.625 (2)	0.179 (8)	0.689 (10)
H15A	−0.3317	0.2511	0.5421	0.268*	0.689 (10)
H15B	−0.2273	0.2420	0.7150	0.268*	0.689 (10)
H15C	−0.1668	0.2656	0.5866	0.268*	0.689 (10)
C13'	−0.145 (3)	0.3255 (4)	0.850 (4)	0.122 (10)	0.311 (10)
H13C	−0.1223	0.3089	0.9524	0.147*	0.311 (10)
H13D	−0.0655	0.3192	0.8079	0.147*	0.311 (10)
C14'	−0.282 (3)	0.3044 (10)	0.740 (3)	0.138 (8)	0.311 (10)
H14C	−0.3494	0.3320	0.7049	0.165*	0.311 (10)
H14D	−0.3225	0.2822	0.8020	0.165*	0.311 (10)
C15'	−0.279 (3)	0.2759 (10)	0.595 (3)	0.105 (6)	0.311 (10)
H15D	−0.3770	0.2674	0.5330	0.157*	0.311 (10)
H15E	−0.2233	0.2457	0.6266	0.157*	0.311 (10)
H15F	−0.2361	0.2964	0.5331	0.157*	0.311 (10)
S5	0.33144 (12)	0.34689 (4)	1.15800 (11)	0.0716 (3)
C16	0.3736 (6)	0.29134 (14)	1.0928 (6)	0.0958 (14)
H16A	0.4135	0.2961	1.0065	0.115*	0.689 (10)
H16B	0.4436	0.2731	1.1779	0.115*	0.689 (10)
H16C	0.4545	0.2981	1.0536	0.115*	0.311 (10)
H16D	0.4117	0.2703	1.1861	0.115*	0.311 (10)
C17	0.2338 (8)	0.2642 (2)	1.0379 (10)	0.089 (2)	0.689 (10)
H17A	0.1821	0.2680	1.1147	0.106*	0.689 (10)
H17B	0.1737	0.2780	0.9374	0.106*	0.689 (10)
C18	0.2631 (8)	0.2107 (2)	1.0189 (10)	0.092 (2)	0.689 (10)
H18A	0.3163	0.1958	1.1204	0.111*	0.689 (10)
H18B	0.3194	0.2066	0.9467	0.111*	0.689 (10)
C19	0.1163 (15)	0.1872 (6)	0.952 (3)	0.132 (6)	0.689 (10)
H19A	0.1271	0.1521	0.9337	0.198*	0.689 (10)
H19B	0.0641	0.2033	0.8542	0.198*	0.689 (10)
H19C	0.0632	0.1910	1.0266	0.198*	0.689 (10)
C17'	0.2867 (19)	0.2577 (5)	0.9740 (15)	0.105 (5)	0.311 (10)
H17C	0.3450	0.2356	0.9319	0.126*	0.311 (10)
H17D	0.2157	0.2752	0.8880	0.126*	0.311 (10)
C18'	0.219 (3)	0.2313 (8)	1.081 (2)	0.127 (6)	0.311 (10)
H18C	0.1472	0.2527	1.1031	0.152*	0.311 (10)
H18D	0.2931	0.2231	1.1803	0.152*	0.311 (10)
C19'	0.149 (3)	0.1841 (9)	0.999 (5)	0.118 (10)	0.311 (10)
H19D	0.1170	0.1641	1.0714	0.176*	0.311 (10)
H19E	0.2182	0.1654	0.9641	0.176*	0.311 (10)
H19F	0.0671	0.1927	0.9087	0.176*	0.311 (10)
N1	0.3666 (3)	0.49065 (8)	0.1432 (3)	0.0486 (6)
H1	0.3813	0.5013	0.0580	0.058*
O1	0.6480 (2)	0.46096 (8)	0.1393 (3)	0.0581 (6)
O2	0.6701 (2)	0.42077 (8)	0.3638 (2)	0.0540 (5)
S1	0.44602 (8)	0.42390 (3)	0.54986 (9)	0.0483 (2)
S2	0.15379 (9)	0.47146 (3)	0.44873 (10)	0.0558 (2)
S3	0.09887 (9)	0.43714 (3)	0.76775 (9)	0.0564 (2)
S4	0.38360 (9)	0.39046 (3)	0.87406 (10)	0.0548 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0517 (17)	0.0411 (14)	0.0481 (15)	−0.0027 (12)	0.0276 (13)	0.0018 (12)
C2	0.0472 (16)	0.0381 (13)	0.0444 (14)	−0.0021 (11)	0.0229 (13)	0.0003 (11)
C3	0.0484 (17)	0.0425 (14)	0.0506 (16)	−0.0013 (12)	0.0255 (13)	0.0013 (12)
C4	0.0568 (18)	0.0460 (15)	0.0491 (16)	0.0038 (13)	0.0251 (14)	0.0055 (12)
C5	0.0471 (16)	0.0429 (14)	0.0487 (15)	−0.0026 (12)	0.0259 (13)	0.0010 (12)
C6	0.0496 (17)	0.0474 (15)	0.0467 (16)	−0.0024 (12)	0.0235 (13)	0.0010 (12)
C7	0.0605 (19)	0.0465 (15)	0.0455 (16)	−0.0039 (13)	0.0244 (14)	0.0016 (12)
C8	0.0568 (19)	0.0524 (16)	0.0460 (16)	−0.0051 (14)	0.0277 (14)	0.0034 (13)
C9	0.0504 (17)	0.0474 (15)	0.0500 (16)	−0.0085 (13)	0.0238 (14)	−0.0008 (13)
C10	0.0492 (19)	0.082 (2)	0.075 (2)	0.0094 (17)	0.0266 (17)	0.0141 (19)
C11	0.134 (6)	0.165 (6)	0.179 (7)	0.040 (5)	0.084 (5)	0.022 (5)
S6	0.0676 (6)	0.0819 (6)	0.0619 (5)	−0.0029 (4)	0.0415 (5)	0.0085 (4)
C12	0.063 (2)	0.080 (2)	0.096 (3)	−0.0058 (18)	0.042 (2)	0.006 (2)
C13	0.075 (4)	0.067 (3)	0.104 (6)	−0.010 (3)	0.041 (4)	0.014 (3)
C14	0.072 (4)	0.072 (4)	0.113 (6)	−0.011 (3)	0.037 (4)	0.010 (4)
C15	0.164 (15)	0.094 (8)	0.266 (18)	−0.016 (8)	0.050 (13)	−0.060 (10)
C13'	0.115 (14)	0.089 (9)	0.149 (17)	0.001 (10)	0.021 (13)	0.001 (11)
C14'	0.133 (14)	0.094 (12)	0.166 (17)	−0.024 (11)	0.018 (14)	−0.004 (12)
C15'	0.081 (12)	0.099 (15)	0.132 (12)	−0.022 (11)	0.029 (11)	0.030 (10)
S5	0.0952 (7)	0.0666 (5)	0.0576 (5)	0.0101 (5)	0.0307 (5)	0.0186 (4)
C16	0.120 (4)	0.060 (2)	0.105 (3)	0.011 (2)	0.031 (3)	0.018 (2)
C17	0.112 (5)	0.067 (4)	0.090 (5)	0.007 (3)	0.037 (4)	−0.004 (3)
C18	0.121 (5)	0.060 (3)	0.107 (5)	0.007 (4)	0.051 (4)	−0.003 (3)
C19	0.133 (10)	0.103 (9)	0.152 (11)	−0.035 (9)	0.035 (9)	−0.005 (8)
C17'	0.152 (12)	0.076 (9)	0.122 (10)	−0.009 (7)	0.092 (9)	−0.034 (7)
C18'	0.173 (15)	0.102 (12)	0.140 (13)	−0.015 (10)	0.098 (11)	−0.019 (10)
C19'	0.110 (16)	0.043 (8)	0.20 (3)	0.021 (7)	0.046 (16)	0.032 (10)
N1	0.0611 (16)	0.0467 (13)	0.0473 (13)	0.0003 (11)	0.0302 (12)	0.0063 (11)
O1	0.0600 (13)	0.0686 (13)	0.0588 (13)	−0.0016 (11)	0.0373 (11)	0.0114 (10)
O2	0.0493 (12)	0.0639 (13)	0.0566 (12)	0.0012 (10)	0.0281 (10)	0.0102 (10)
S1	0.0495 (4)	0.0527 (4)	0.0506 (4)	0.0049 (3)	0.0271 (3)	0.0094 (3)
S2	0.0520 (5)	0.0668 (5)	0.0599 (5)	0.0112 (4)	0.0336 (4)	0.0159 (4)
S3	0.0546 (5)	0.0706 (5)	0.0541 (5)	0.0094 (4)	0.0315 (4)	0.0154 (4)
S4	0.0523 (5)	0.0657 (5)	0.0522 (4)	0.0051 (4)	0.0247 (4)	0.0095 (4)

Geometric parameters (Å, º) top

C1—N1	1.345 (4)	C14—H14B	0.9700
C1—C2	1.385 (4)	C15—H15A	0.9600
C1—C9	1.427 (4)	C15—H15B	0.9600
C2—C3	1.383 (4)	C15—H15C	0.9600
C2—S1	1.704 (3)	C13'—C14'	1.484 (9)
C3—C4	1.358 (4)	C13'—H13C	0.9700
C3—S2	1.738 (3)	C13'—H13D	0.9700
C4—N1	1.350 (4)	C14'—C15'	1.501 (9)
C4—H4	0.9300	C14'—H14C	0.9700
C5—C6	1.333 (4)	C14'—H14D	0.9700
C5—S2	1.728 (3)	C15'—H15D	0.9600
C5—S1	1.765 (3)	C15'—H15E	0.9600
C6—S4	1.720 (3)	C15'—H15F	0.9600
C6—S3	1.754 (3)	S5—C16	1.684 (4)
C7—C8	1.327 (4)	C16—C17'	1.435 (9)
C7—S5	1.718 (3)	C16—C17	1.475 (7)
C7—S4	1.753 (3)	C16—H16A	0.9700
C8—S3	1.713 (3)	C16—H16B	0.9700
C8—S6	1.748 (3)	C16—H16C	0.9700
C9—O1	1.206 (3)	C16—H16D	0.9700
C9—O2	1.306 (4)	C17—C18	1.473 (7)
C10—O2	1.419 (4)	C17—H17A	0.9700
C10—C11	1.496 (4)	C17—H17B	0.9700
C10—H10A	0.9700	C18—C19	1.495 (8)
C10—H10B	0.9700	C18—H18A	0.9700
C11—H11A	0.9600	C18—H18B	0.9700
C11—H11B	0.9600	C19—H19A	0.9600
C11—H11C	0.9600	C19—H19B	0.9600
S6—C12	1.808 (4)	C19—H19C	0.9600
C12—C13	1.437 (6)	C17'—C18'	1.485 (9)
C12—C13'	1.444 (9)	C17'—H17C	0.9700
C12—H12A	0.9700	C17'—H17D	0.9700
C12—H12B	0.9700	C18'—C19'	1.503 (9)
C12—H12C	0.9700	C18'—H18C	0.9700
C12—H12D	0.9700	C18'—H18D	0.9700
C13—C14	1.491 (7)	C19'—H19D	0.9600
C13—H13A	0.9700	C19'—H19E	0.9600
C13—H13B	0.9700	C19'—H19F	0.9600
C14—C15	1.524 (4)	N1—H1	0.8600
C14—H14A	0.9700

N1—C1—C2	106.2 (2)	C12—C13'—H13D	109.5
N1—C1—C9	121.5 (2)	C14'—C13'—H13D	109.5
C2—C1—C9	132.3 (3)	H13C—C13'—H13D	108.1
C3—C2—C1	108.4 (3)	C13'—C14'—C15'	120 (3)
C3—C2—S1	116.9 (2)	C13'—C14'—H14C	107.3
C1—C2—S1	134.7 (2)	C15'—C14'—H14C	107.3
C4—C3—C2	106.7 (3)	C13'—C14'—H14D	107.3
C4—C3—S2	135.3 (2)	C15'—C14'—H14D	107.3
C2—C3—S2	118.0 (2)	H14C—C14'—H14D	106.9
N1—C4—C3	108.5 (3)	C14'—C15'—H15D	109.5
N1—C4—H4	125.8	C14'—C15'—H15E	109.5
C3—C4—H4	125.8	H15D—C15'—H15E	109.5
C6—C5—S2	120.6 (2)	C14'—C15'—H15F	109.5
C6—C5—S1	122.9 (2)	H15D—C15'—H15F	109.5
S2—C5—S1	116.44 (15)	H15E—C15'—H15F	109.5
C5—C6—S4	123.6 (2)	C16—S5—C7	100.3 (2)
C5—C6—S3	123.3 (2)	C17'—C16—C17	35.7 (6)
S4—C6—S3	113.05 (15)	C17'—C16—S5	130.5 (8)
C8—C7—S5	124.1 (2)	C17—C16—S5	104.2 (4)
C8—C7—S4	118.3 (2)	C17'—C16—H16A	77.8
S5—C7—S4	116.94 (19)	C17—C16—H16A	110.9
C7—C8—S3	115.6 (2)	S5—C16—H16A	110.9
C7—C8—S6	126.6 (2)	C17'—C16—H16B	111.4
S3—C8—S6	117.47 (18)	C17—C16—H16B	110.9
O1—C9—O2	123.3 (3)	S5—C16—H16B	110.9
O1—C9—C1	126.2 (3)	H16A—C16—H16B	108.9
O2—C9—C1	110.5 (2)	C17'—C16—H16C	101.8
O2—C10—C11	104.8 (3)	C17—C16—H16C	137.3
O2—C10—H10A	110.8	S5—C16—H16C	105.7
C11—C10—H10A	110.8	H16A—C16—H16C	28.6
O2—C10—H10B	110.8	H16B—C16—H16C	85.8
C11—C10—H10B	110.8	C17'—C16—H16D	104.2
H10A—C10—H10B	108.9	C17—C16—H16D	93.6
C10—C11—H11A	109.5	S5—C16—H16D	106.3
C10—C11—H11B	109.5	H16A—C16—H16D	127.6
H11A—C11—H11B	109.5	H16B—C16—H16D	20.6
C10—C11—H11C	109.5	H16C—C16—H16D	106.3
H11A—C11—H11C	109.5	C18—C17—C16	108.7 (6)
H11B—C11—H11C	109.5	C18—C17—H17A	110.0
C8—S6—C12	101.55 (17)	C16—C17—H17A	110.0
C13—C12—C13'	18.5 (16)	C18—C17—H17B	110.0
C13—C12—S6	115.1 (5)	C16—C17—H17B	110.0
C13'—C12—S6	106.3 (12)	H17A—C17—H17B	108.3
C13—C12—H12A	108.5	C17—C18—C19	104.9 (9)
C13'—C12—H12A	97.8	C17—C18—H18A	110.8
S6—C12—H12A	108.5	C19—C18—H18A	110.8
C13—C12—H12B	108.5	C17—C18—H18B	110.8
C13'—C12—H12B	126.8	C19—C18—H18B	110.8
S6—C12—H12B	108.5	H18A—C18—H18B	108.9
H12A—C12—H12B	107.5	C18—C19—H19A	109.5
C13—C12—H12C	117.9	C18—C19—H19B	109.5
C13'—C12—H12C	109.6	H19A—C19—H19B	109.5
S6—C12—H12C	109.9	C18—C19—H19C	109.5
H12A—C12—H12C	13.5	H19A—C19—H19C	109.5
H12B—C12—H12C	94.7	H19B—C19—H19C	109.5
C13—C12—H12D	94.6	C16—C17'—C18'	95.7 (11)
C13'—C12—H12D	113.1	C16—C17'—H17C	112.6
S6—C12—H12D	109.7	C18'—C17'—H17C	112.6
H12A—C12—H12D	120.2	C16—C17'—H17D	112.6
H12B—C12—H12D	15.7	C18'—C17'—H17D	112.6
H12C—C12—H12D	108.2	H17C—C17'—H17D	110.1
C12—C13—C14	113.2 (7)	C17'—C18'—C19'	108 (2)
C12—C13—H13A	108.9	C17'—C18'—H18C	110.1
C14—C13—H13A	108.9	C19'—C18'—H18C	110.1
C12—C13—H13B	108.9	C17'—C18'—H18D	110.1
C14—C13—H13B	108.9	C19'—C18'—H18D	110.1
H13A—C13—H13B	107.8	H18C—C18'—H18D	108.4
C13—C14—C15	103.5 (10)	C18'—C19'—H19D	109.5
C13—C14—H14A	111.1	C18'—C19'—H19E	109.5
C15—C14—H14A	111.1	H19D—C19'—H19E	109.5
C13—C14—H14B	111.1	C18'—C19'—H19F	109.5
C15—C14—H14B	111.1	H19D—C19'—H19F	109.5
H14A—C14—H14B	109.0	H19E—C19'—H19F	109.5
C14—C15—H15A	109.5	C1—N1—C4	110.2 (2)
C14—C15—H15B	109.5	C1—N1—H1	124.9
H15A—C15—H15B	109.5	C4—N1—H1	124.9
C14—C15—H15C	109.5	C9—O2—C10	115.5 (2)
H15A—C15—H15C	109.5	C2—S1—C5	94.82 (13)
H15B—C15—H15C	109.5	C5—S2—C3	93.89 (14)
C12—C13'—C14'	110.6 (18)	C8—S3—C6	96.81 (14)
C12—C13'—H13C	109.5	C6—S4—C7	94.90 (14)
C14'—C13'—H13C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	1.96	2.782 (3)	160

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₅NO₂S₆
M_r	491.76
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	288
a, b, c (Å)	9.687 (3), 26.608 (9), 8.876 (5)
β (°)	108.408 (17)
V (Å³)	2170.7 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.65
Crystal size (mm)	0.48 × 0.18 × 0.17

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.747, 0.898
No. of measured, independent and observed [I > 2σ(I)] reflections	17087, 3823, 3114
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.120, 1.04
No. of reflections	3823
No. of parameters	309
No. of restraints	188
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.71

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	1.96	2.782 (3)	159.5

Symmetry code: (i) −x+1, −y+1, −z.

Acknowledgements

The authors acknowledge financial support from the National Natural Science Foundation of Jilin Province (grant No. 20101548).

References

Hansel, J. A., Becher, J., Jeppesen, J. O., Levilain, E., Nielsen, M. B., Petersen, B. M., Petersen, J. C. & Sahin, Y. (2004). J. Mater. Chem. 14, 179–184. Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Hou, R. B., Su, C., Kan, Y. H., Gu, L. Y. & Yin, B. Z. (2010). Sens. Lett. 8, 308–313. Web of Science CrossRef CAS Google Scholar
Hou, R.-B. & Yin, B.-Z. (2010). Acta Cryst. E66, o3353. Web of Science CSD CrossRef IUCr Journals Google Scholar
Jeppesen, J. O., Takimiya, K., Jensen, F. & Becher, J. (1999). Org. Lett. 1, 1291–1294. Web of Science CSD CrossRef CAS Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalStructure. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 5| May 2012| Page o1400

doi:10.1107/S1600536812015309

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

Ethyl 2-[4,5-bis­­(butyl­sulfan­yl)-1,3-di­thiol-2-yl­­idene]-1,3-di­thiolo[4,5-c]pyrrole-4-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Ethyl 2-[4,5-bis(butylsulfanyl)-1,3-dithiol-2-ylidene]-1,3-dithiolo[4,5-c]pyrrole-4-carboxylate