2-[4,5-Bis(butyl­sulfan­yl)-1,3-dithiol-2-yl­idene]-5-methyl-5H-1,3-dithiolo[4,5-c]pyrrole-4-carbaldehyde

Hou, R.-B.; Yin, B.-Z.

doi:10.1107/S160053681004910X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3353

https://doi.org/10.1107/S160053681004910X

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2-[4,5-Bis(butylsulfanyl)-1,3-dithiol-2-ylidene]-5-methyl-5H-1,3-dithiolo[4,5-c]pyrrole-4-carbaldehyde

Rui-Bin Hou ^a and Bing-Zhu Yin ^a ^*

^aKey Laboratory of Natural Resources of Changbai Mountain & Functional Molecules (Yanbian University), Ministry of Education, Yanji 133002, People's Republic of China
^*Correspondence e-mail: zqcong@ybu.edu.cn

(Received 22 November 2010; accepted 24 November 2010; online 30 November 2010)

In the title compound, C₁₈H₂₃NOS₆, the dithiolopyrrole ring is almost planar [r.m.s. deviation = 0.044 (3) Å] and makes a dihedral angle of 25.11 (7)° with the dithiole ring. In the crystal, pairs of neighboring molecules are connected by weak intermolecular C—H⋯O interactions. These dimers are further linked into a chain along [110] by C—H⋯O interactions.

Related literature

For background to tetrathiafulvalenes, see: Jeppesen et al. (1999 ); Hansel et al. (2004 ). For the synthesis, see: An et al. (2009 ). For a related structure, see: Leng et al. (2009 )

Experimental

Crystal data

C₁₈H₂₃NOS₆
M_r = 461.73
Triclinic, $[P \overline 1]$
a = 7.4227 (15) Å
b = 8.8356 (18) Å
c = 17.811 (4) Å
α = 93.44 (3)°
β = 99.37 (3)°
γ = 105.31 (3)°
V = 1105.1 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.63 mm⁻¹
T = 291 K
0.12 × 0.11 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.929, T_max = 0.940
10707 measured reflections
4956 independent reflections
3298 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.176
S = 1.06
4956 reflections
238 parameters
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3B⋯O1ⁱ	0.97	2.79	3.444 (5)	125
C4—H4A⋯O1ⁱ	0.97	2.71	3.368 (5)	126
C18—H18⋯O1ⁱⁱ	0.93	2.58	3.412 (5)	150
Symmetry codes: (i) x+1, y+1, z; (ii) -x, -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: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681004910X/ng5074sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681004910X/ng5074Isup2.hkl

checkCIF report

Comment top

The tetrathiafulvalenes (TTFs) have become an interesting theme of organic synthesis (Jeppesen et al., 1999). This is due to the high electrical conductivity and super conductor properties of these highly sophisticated compounds. Becher has recently synthesized a series novel donor-π-acceptor dyads based on the monopyrrolo-TTF (MPTTF), which exhibit good third-order non-linear optical properties (Hansel et al. 2004). In this paper, we report the crystal structure of the title compound, which is a key precursor of the dyads.

The title compound, as shown in Fig. 1, all bond lengths and angles are normal and comparable with those reported for the related structure (Leng et al., 2009). In the title compound, the dithiolopyrrole ring and attached C16, C18 and O1 atoms are nearlly coplanar [mean deviation from the mean plane = 0.044 (3) Å. The dihedral angle between the dithiolopyrrole ring and dithiole ring is 25.11 (7) °. In the crystal, weak C—H···O hydrogen bonds (table 1) link the molecules into dimer firstly and the dimers are further linked to form one-dimensional chain along [a+b] direction.

Related literature top

For background to tetrathiafulvalenes, see: Jeppesen et al. (1999); Hansel et al. (2004). For the synthesis, see: An et al. (2009). For a related structure, see: Leng et al. (2009)

Experimental top

The title compound was prepared according to literature (An et al., 2009). Crystals suitable for single-crystal X-ray diffraction were grown by recrystallization from mixture of dichloromethane and petroleum (60–90 °C).

Structure description top

For background to tetrathiafulvalenes, see: Jeppesen et al. (1999); Hansel et al. (2004). For the synthesis, see: An et al. (2009). For a related structure, see: Leng et al. (2009)

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

Fig. 1. The asymmetric of title compound, with the atom numbering. Displacement ellipsoids of non-H atoms are drawn at the 30% probalility level.

2-[4,5-Bis(butylsulfanyl)-1,3-dithiol-2-ylidene]-5-methyl-5H- 1,3-dithiolo[4,5-c]pyrrole-4-carbaldehyde top

Crystal data top

C₁₈H₂₃NOS₆	Z = 2
M_r = 461.73	F(000) = 484
Triclinic, P1	D_x = 1.388 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4227 (15) Å	Cell parameters from 7048 reflections
b = 8.8356 (18) Å	θ = 3.2–27.4°
c = 17.811 (4) Å	µ = 0.63 mm⁻¹
α = 93.44 (3)°	T = 291 K
β = 99.37 (3)°	Block, yellow
γ = 105.31 (3)°	0.12 × 0.11 × 0.10 mm
V = 1105.1 (4) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	4956 independent reflections
Radiation source: fine-focus sealed tube	3298 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ω scans	θ_max = 27.5°, θ_min = 3.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −9→9
T_min = 0.929, T_max = 0.940	k = −11→11
10707 measured reflections	l = −23→23

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.176	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.103P)²] where P = (F_o² + 2F_c²)/3
4956 reflections	(Δ/σ)_max = 0.001
238 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

C₁₈H₂₃NOS₆	γ = 105.31 (3)°
M_r = 461.73	V = 1105.1 (4) Å³
Triclinic, P1	Z = 2
a = 7.4227 (15) Å	Mo Kα radiation
b = 8.8356 (18) Å	µ = 0.63 mm⁻¹
c = 17.811 (4) Å	T = 291 K
α = 93.44 (3)°	0.12 × 0.11 × 0.10 mm
β = 99.37 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4956 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3298 reflections with I > 2σ(I)
T_min = 0.929, T_max = 0.940	R_int = 0.035
10707 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.176	H-atom parameters constrained
S = 1.06	Δρ_max = 0.51 e Å⁻³
4956 reflections	Δρ_min = −0.44 e Å⁻³
238 parameters

Special details top

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
C1	1.3588 (7)	0.8577 (6)	0.3605 (3)	0.0992 (16)
H1A	1.4403	0.8569	0.3239	0.149*
H1B	1.4309	0.8665	0.4113	0.149*
H1C	1.3067	0.9459	0.3554	0.149*
C2	1.2000 (6)	0.7069 (5)	0.3463 (2)	0.0746 (11)
H2A	1.2529	0.6206	0.3598	0.090*
H2B	1.1120	0.7139	0.3802	0.090*
C3	1.0910 (6)	0.6676 (5)	0.2657 (2)	0.0685 (10)
H3A	1.0039	0.5628	0.2612	0.082*
H3B	1.1798	0.6642	0.2317	0.082*
C4	0.9789 (5)	0.7804 (5)	0.2387 (2)	0.0612 (9)
H4A	0.9227	0.7494	0.1851	0.073*
H4B	1.0656	0.8853	0.2429	0.073*
C5	1.0794 (8)	0.1668 (7)	0.4134 (3)	0.1074 (17)
H5A	1.0622	0.1460	0.3588	0.161*
H5B	1.1150	0.0815	0.4370	0.161*
H5C	1.1778	0.2634	0.4305	0.161*
C6	0.8994 (9)	0.1813 (7)	0.4347 (3)	0.1053 (17)
H6A	0.7974	0.0886	0.4120	0.126*
H6B	0.9111	0.1849	0.4899	0.126*
C7	0.8498 (7)	0.3235 (6)	0.4094 (3)	0.0837 (13)
H7A	0.8372	0.3194	0.3542	0.100*
H7B	0.9524	0.4161	0.4317	0.100*
C8	0.6652 (7)	0.3397 (5)	0.4319 (2)	0.0735 (11)
H8A	0.6734	0.3350	0.4866	0.088*
H8B	0.5604	0.2521	0.4059	0.088*
C9	0.6295 (5)	0.6022 (4)	0.26157 (16)	0.0458 (7)
C10	0.5642 (5)	0.4948 (4)	0.30804 (17)	0.0483 (7)
C11	0.4100 (4)	0.3654 (3)	0.17027 (16)	0.0445 (7)
C12	0.3512 (4)	0.2543 (3)	0.10934 (16)	0.0438 (7)
C13	0.2413 (4)	−0.0068 (3)	0.02430 (17)	0.0440 (7)
C14	0.3053 (4)	0.1071 (3)	−0.02319 (16)	0.0439 (7)
C15	0.2900 (5)	0.0300 (4)	−0.09493 (18)	0.0525 (8)
H15	0.3207	0.0776	−0.1381	0.063*
C16	0.1719 (6)	−0.2460 (5)	−0.1579 (2)	0.0688 (10)
H16A	0.0363	−0.2788	−0.1743	0.103*
H16B	0.2154	−0.3354	−0.1440	0.103*
H16C	0.2307	−0.2022	−0.1989	0.103*
C17	0.1886 (5)	−0.1548 (4)	−0.01838 (19)	0.0510 (7)
C18	0.1247 (6)	−0.3038 (4)	0.0080 (2)	0.0639 (9)
H18	0.0960	−0.3934	−0.0267	0.077*
N1	0.2228 (4)	−0.1257 (3)	−0.09119 (15)	0.0526 (7)
O1	0.1051 (5)	−0.3211 (3)	0.07376 (16)	0.0820 (9)
S1	0.79120 (13)	0.78869 (10)	0.29159 (5)	0.0561 (3)
S2	0.61844 (16)	0.52311 (12)	0.40750 (5)	0.0659 (3)
S3	0.38334 (14)	0.32527 (10)	0.26366 (5)	0.0567 (3)
S4	0.52382 (14)	0.56342 (9)	0.16415 (4)	0.0536 (2)
S5	0.37538 (13)	0.30352 (9)	0.01664 (4)	0.0524 (2)
S6	0.24240 (13)	0.05437 (9)	0.11878 (4)	0.0516 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.068 (3)	0.109 (4)	0.115 (4)	0.023 (3)	0.011 (3)	−0.006 (3)
C2	0.074 (3)	0.087 (3)	0.069 (3)	0.035 (2)	0.011 (2)	0.010 (2)
C3	0.073 (3)	0.068 (2)	0.066 (2)	0.018 (2)	0.023 (2)	−0.0010 (19)
C4	0.061 (2)	0.070 (2)	0.0535 (19)	0.0135 (18)	0.0181 (17)	0.0137 (17)
C5	0.099 (4)	0.107 (4)	0.122 (5)	0.039 (3)	0.027 (3)	−0.005 (3)
C6	0.125 (5)	0.117 (4)	0.099 (4)	0.061 (4)	0.046 (3)	0.022 (3)
C7	0.103 (4)	0.083 (3)	0.072 (3)	0.031 (3)	0.027 (3)	0.009 (2)
C8	0.094 (3)	0.082 (3)	0.050 (2)	0.032 (2)	0.012 (2)	0.0188 (19)
C9	0.0491 (17)	0.0483 (16)	0.0380 (15)	0.0111 (14)	0.0081 (13)	−0.0007 (12)
C10	0.0561 (19)	0.0532 (17)	0.0366 (15)	0.0176 (15)	0.0089 (14)	0.0004 (13)
C11	0.0497 (18)	0.0417 (15)	0.0383 (15)	0.0053 (13)	0.0094 (13)	0.0053 (12)
C12	0.0484 (17)	0.0414 (14)	0.0378 (14)	0.0038 (13)	0.0107 (13)	0.0066 (12)
C13	0.0437 (16)	0.0421 (15)	0.0410 (15)	0.0058 (13)	0.0039 (13)	0.0028 (12)
C14	0.0460 (17)	0.0414 (15)	0.0388 (15)	0.0052 (13)	0.0042 (13)	0.0038 (12)
C15	0.060 (2)	0.0524 (18)	0.0425 (16)	0.0105 (16)	0.0079 (15)	0.0079 (14)
C16	0.072 (3)	0.064 (2)	0.061 (2)	0.0154 (19)	0.0018 (19)	−0.0205 (18)
C17	0.0520 (19)	0.0439 (16)	0.0504 (18)	0.0074 (14)	0.0010 (14)	0.0021 (13)
C18	0.072 (2)	0.0439 (17)	0.069 (2)	0.0075 (17)	0.0110 (19)	0.0014 (16)
N1	0.0560 (17)	0.0517 (15)	0.0452 (14)	0.0140 (13)	0.0012 (12)	−0.0056 (12)
O1	0.109 (2)	0.0570 (15)	0.0691 (18)	0.0038 (15)	0.0158 (17)	0.0148 (13)
S1	0.0593 (5)	0.0486 (4)	0.0552 (5)	0.0078 (4)	0.0121 (4)	−0.0066 (4)
S2	0.0881 (7)	0.0735 (6)	0.0349 (4)	0.0241 (5)	0.0069 (4)	0.0004 (4)
S3	0.0694 (6)	0.0540 (5)	0.0389 (4)	0.0006 (4)	0.0148 (4)	0.0056 (3)
S4	0.0736 (6)	0.0425 (4)	0.0383 (4)	0.0066 (4)	0.0071 (4)	0.0051 (3)
S5	0.0704 (6)	0.0412 (4)	0.0381 (4)	0.0023 (4)	0.0097 (4)	0.0066 (3)
S6	0.0623 (5)	0.0431 (4)	0.0422 (4)	−0.0001 (4)	0.0128 (4)	0.0074 (3)

Geometric parameters (Å, º) top

C1—C2	1.504 (6)	C9—C10	1.342 (5)
C1—H1A	0.9600	C9—S1	1.756 (3)
C1—H1B	0.9600	C9—S4	1.757 (3)
C1—H1C	0.9600	C10—S2	1.739 (3)
C2—C3	1.500 (5)	C10—S3	1.767 (3)
C2—H2A	0.9700	C11—C12	1.350 (4)
C2—H2B	0.9700	C11—S4	1.749 (3)
C3—C4	1.510 (5)	C11—S3	1.753 (3)
C3—H3A	0.9700	C12—S5	1.757 (3)
C3—H3B	0.9700	C12—S6	1.769 (3)
C4—S1	1.818 (3)	C13—C14	1.391 (4)
C4—H4A	0.9700	C13—C17	1.399 (4)
C4—H4B	0.9700	C13—S6	1.734 (3)
C5—C6	1.482 (7)	C14—C15	1.385 (4)
C5—H5A	0.9600	C14—S5	1.744 (3)
C5—H5B	0.9600	C15—N1	1.344 (4)
C5—H5C	0.9600	C15—H15	0.9300
C6—C7	1.475 (7)	C16—N1	1.475 (4)
C6—H6A	0.9700	C16—H16A	0.9600
C6—H6B	0.9700	C16—H16B	0.9600
C7—C8	1.528 (6)	C16—H16C	0.9600
C7—H7A	0.9700	C17—N1	1.387 (4)
C7—H7B	0.9700	C17—C18	1.413 (5)
C8—S2	1.807 (4)	C18—O1	1.217 (5)
C8—H8A	0.9700	C18—H18	0.9300
C8—H8B	0.9700

C2—C1—H1A	109.5	C7—C8—H8B	109.3
C2—C1—H1B	109.5	S2—C8—H8B	109.3
H1A—C1—H1B	109.5	H8A—C8—H8B	107.9
C2—C1—H1C	109.5	C10—C9—S1	125.3 (2)
H1A—C1—H1C	109.5	C10—C9—S4	117.4 (2)
H1B—C1—H1C	109.5	S1—C9—S4	116.88 (18)
C3—C2—C1	115.1 (4)	C9—C10—S2	125.1 (3)
C3—C2—H2A	108.5	C9—C10—S3	116.0 (2)
C1—C2—H2A	108.5	S2—C10—S3	118.30 (19)
C3—C2—H2B	108.5	C12—C11—S4	123.3 (2)
C1—C2—H2B	108.5	C12—C11—S3	123.5 (2)
H2A—C2—H2B	107.5	S4—C11—S3	113.19 (16)
C2—C3—C4	115.4 (3)	C11—C12—S5	121.2 (2)
C2—C3—H3A	108.4	C11—C12—S6	121.7 (2)
C4—C3—H3A	108.4	S5—C12—S6	117.09 (16)
C2—C3—H3B	108.4	C14—C13—C17	108.2 (3)
C4—C3—H3B	108.4	C14—C13—S6	118.5 (2)
H3A—C3—H3B	107.5	C17—C13—S6	133.4 (3)
C3—C4—S1	114.2 (3)	C15—C14—C13	107.6 (3)
C3—C4—H4A	108.7	C15—C14—S5	135.4 (2)
S1—C4—H4A	108.7	C13—C14—S5	117.0 (2)
C3—C4—H4B	108.7	N1—C15—C14	107.9 (3)
S1—C4—H4B	108.7	N1—C15—H15	126.0
H4A—C4—H4B	107.6	C14—C15—H15	126.0
C6—C5—H5A	109.5	N1—C16—H16A	109.5
C6—C5—H5B	109.5	N1—C16—H16B	109.5
H5A—C5—H5B	109.5	H16A—C16—H16B	109.5
C6—C5—H5C	109.5	N1—C16—H16C	109.5
H5A—C5—H5C	109.5	H16A—C16—H16C	109.5
H5B—C5—H5C	109.5	H16B—C16—H16C	109.5
C7—C6—C5	112.5 (5)	N1—C17—C13	105.7 (3)
C7—C6—H6A	109.1	N1—C17—C18	126.9 (3)
C5—C6—H6A	109.1	C13—C17—C18	127.3 (3)
C7—C6—H6B	109.1	O1—C18—C17	123.6 (3)
C5—C6—H6B	109.1	O1—C18—H18	118.2
H6A—C6—H6B	107.8	C17—C18—H18	118.2
C6—C7—C8	112.7 (4)	C15—N1—C17	110.6 (3)
C6—C7—H7A	109.0	C15—N1—C16	124.0 (3)
C8—C7—H7A	109.0	C17—N1—C16	125.0 (3)
C6—C7—H7B	109.0	C9—S1—C4	101.26 (16)
C8—C7—H7B	109.0	C10—S2—C8	102.69 (17)
H7A—C7—H7B	107.8	C11—S3—C10	94.65 (15)
C7—C8—S2	111.8 (3)	C11—S4—C9	94.30 (15)
C7—C8—H8A	109.3	C14—S5—C12	93.61 (14)
S2—C8—H8A	109.3	C13—S6—C12	93.09 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3B···O1ⁱ	0.97	2.79	3.444 (5)	125
C4—H4A···O1ⁱ	0.97	2.71	3.368 (5)	126
C18—H18···O1ⁱⁱ	0.93	2.58	3.412 (5)	150

Symmetry codes: (i) x+1, y+1, z; (ii) −x, −y−1, −z.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₃NOS₆
M_r	461.73
Crystal system, space group	Triclinic, P1
Temperature (K)	291
a, b, c (Å)	7.4227 (15), 8.8356 (18), 17.811 (4)
α, β, γ (°)	93.44 (3), 99.37 (3), 105.31 (3)
V (Å³)	1105.1 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.63
Crystal size (mm)	0.12 × 0.11 × 0.10

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.929, 0.940
No. of measured, independent and observed [I > 2σ(I)] reflections	10707, 4956, 3298
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.176, 1.06
No. of reflections	4956
No. of parameters	238
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.44

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3B···O1ⁱ	0.97	2.79	3.444 (5)	125.0
C4—H4A···O1ⁱ	0.97	2.71	3.368 (5)	125.9
C18—H18···O1ⁱⁱ	0.93	2.58	3.412 (5)	149.6

Symmetry codes: (i) x+1, y+1, z; (ii) −x, −y−1, −z.

Acknowledgements

The authors acknowledge financial support from the National Natural Science Foundation of China (grant No. 20662010), the Specialized Research Fund for the Doctoral Programme of Higher Education (grant No. 2006184001) and the Open Project of the State Key Laboratory of Supramolecular Structure and Materials, Jilin University.

References

An, C. X., Hou, R. B., Qiu, H., Zhao, J., Yin, B. Z. & Su, Z. M. (2009). Chin. J. Appl. Chem. 26, 795–800. CAS Google Scholar
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
Jeppesen, J. O., Takimiya, K., Jensen, F. & Becher, J. (1999). Org. Lett. 1, 1291–1294. Web of Science CSD CrossRef CAS Google Scholar
Leng, F.-S., Li, B., Yin, B.-Z. & Wu, L.-X. (2009). Acta Cryst. E65, o3092. Web of Science CSD CrossRef IUCr Journals 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

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Volume 66| Part 12| December 2010| Page o3353

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

2-[4,5-Bis(butyl­sulfan­yl)-1,3-di­thiol-2-yl­­idene]-5-methyl-5H-1,3-di­thiolo[4,5-c]pyrrole-4-carbaldehyde

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-[4,5-Bis(butylsulfanyl)-1,3-dithiol-2-ylidene]-5-methyl-5H-1,3-dithiolo[4,5-c]pyrrole-4-carbaldehyde