N,N'-Bis[(E)-(5-chloro-2-thienyl)methyl-idene]ethane-1,2-diamine.

The full mol-ecule of the title compound, C(12)H(10)Cl(2)N(2)S(2), is generated by the application of a centre of inversion. The thio-phene and imine residues are co-planar [the N-C-C-S torsion angle is -2.5 (4)°] and the conformation about the imine bond [1.268 (4) Å] is E. Supra-molecular arrays are formed in the bc plane via C-Cl⋯π inter-actions and these stack along the a axis.

Related literature

For background to 2-substituted thio­phenes, see: Campaigne (1984 ▶); Kleemann et al. (2006 ▶). For related structures, see: Wang et al. (2007 ▶); Wardell et al. (2010 ▶); Prasath et al. (2010 ▶).

Experimental

Crystal data

C12H10Cl2N2S2

M = 317.24

Monoclinic,

a = 14.682 (2) Å

b = 4.7016 (7) Å

c = 10.6607 (15) Å

β = 109.439 (2)°

V = 693.92 (17) Å3

Z = 2

Mo Kα radiation

μ = 0.75 mm−1

T = 100 K

0.25 × 0.15 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.835, T max = 0.963

5721 measured reflections

1576 independent reflections

1270 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.117

S = 1.01

1576 reflections

82 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.48 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681004167X/hg2729sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004167X/hg2729Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H10Cl2N2S2	F(000) = 324
Mr = 317.24	Dx = 1.518 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2363 reflections
a = 14.682 (2) Å	θ = 3.0–28.0°
b = 4.7016 (7) Å	µ = 0.75 mm−1
c = 10.6607 (15) Å	T = 100 K
β = 109.439 (2)°	Prism, colourless
V = 693.92 (17) Å3	0.25 × 0.15 × 0.05 mm
Z = 2

Bruker SMART APEX diffractometer	1576 independent reflections
Radiation source: fine-focus sealed tube	1270 reflections with I > 2σ(I)
graphite	Rint = 0.058
ω scans	θmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→18
Tmin = 0.835, Tmax = 0.963	k = −6→6
5721 measured reflections	l = −13→13

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0662P)2 + 0.3727P] where P = (Fo2 + 2Fc2)/3
1576 reflections	(Δ/σ)max = 0.001
82 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.48 e Å−3

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
Cl1	0.94014 (5)	1.46904 (14)	0.80609 (6)	0.0258 (2)
S1	0.76180 (5)	1.12742 (14)	0.69149 (6)	0.0220 (2)
N1	0.58522 (16)	0.7601 (5)	0.6104 (2)	0.0286 (5)
C1	0.4988 (2)	0.5840 (6)	0.5603 (3)	0.0333 (7)
H1A	0.4406	0.7062	0.5355	0.040*
H1B	0.4955	0.4514	0.6308	0.040*
C2	0.63515 (19)	0.7367 (6)	0.7325 (3)	0.0267 (6)
H2	0.6151	0.6077	0.7868	0.032*
C3	0.72211 (19)	0.9026 (5)	0.7907 (3)	0.0238 (6)
C4	0.7822 (2)	0.9074 (6)	0.9193 (3)	0.0282 (6)
H4	0.7716	0.7970	0.9879	0.034*
C5	0.8620 (2)	1.0934 (6)	0.9411 (3)	0.0271 (6)
H5	0.9109	1.1220	1.0247	0.033*
C6	0.85924 (19)	1.2254 (6)	0.8263 (2)	0.0220 (5)

	U11	U22	U33	U12	U13	U23
Cl1	0.0284 (4)	0.0242 (4)	0.0285 (3)	−0.0067 (2)	0.0141 (3)	−0.0066 (2)
S1	0.0249 (4)	0.0199 (4)	0.0230 (3)	−0.0031 (2)	0.0104 (3)	−0.0007 (2)
N1	0.0241 (12)	0.0212 (12)	0.0432 (14)	−0.0047 (9)	0.0149 (10)	−0.0032 (10)
C1	0.0288 (15)	0.0285 (15)	0.0463 (18)	−0.0089 (12)	0.0173 (13)	−0.0043 (13)
C2	0.0302 (14)	0.0184 (13)	0.0402 (16)	−0.0028 (11)	0.0232 (12)	−0.0029 (11)
C3	0.0287 (14)	0.0169 (13)	0.0323 (14)	−0.0025 (10)	0.0187 (12)	−0.0013 (10)
C4	0.0416 (17)	0.0220 (14)	0.0274 (13)	−0.0028 (12)	0.0202 (12)	0.0001 (10)
C5	0.0353 (15)	0.0261 (15)	0.0219 (12)	−0.0025 (11)	0.0122 (11)	−0.0033 (10)
C6	0.0259 (13)	0.0188 (13)	0.0241 (12)	−0.0002 (10)	0.0122 (10)	−0.0050 (9)

Cl1—C6	1.714 (3)	C2—C3	1.448 (4)
S1—C6	1.719 (3)	C2—H2	0.9500
S1—C3	1.728 (3)	C3—C4	1.362 (4)
N1—C2	1.268 (4)	C4—C5	1.419 (4)
N1—C1	1.459 (3)	C4—H4	0.9500
C1—C1i	1.519 (6)	C5—C6	1.361 (4)
C1—H1A	0.9900	C5—H5	0.9500
C1—H1B	0.9900
C6—S1—C3	90.50 (13)	C4—C3—S1	111.7 (2)
C2—N1—C1	117.5 (2)	C2—C3—S1	119.7 (2)
N1—C1—C1i	110.1 (3)	C3—C4—C5	113.4 (2)
N1—C1—H1A	109.6	C3—C4—H4	123.3
C1i—C1—H1A	109.6	C5—C4—H4	123.3
N1—C1—H1B	109.6	C6—C5—C4	111.0 (3)
C1i—C1—H1B	109.6	C6—C5—H5	124.5
H1A—C1—H1B	108.2	C4—C5—H5	124.5
N1—C2—C3	121.3 (2)	C5—C6—Cl1	127.1 (2)
N1—C2—H2	119.4	C5—C6—S1	113.4 (2)
C3—C2—H2	119.4	Cl1—C6—S1	119.53 (15)
C4—C3—C2	128.6 (2)
C2—N1—C1—C1i	−126.6 (3)	S1—C3—C4—C5	0.0 (3)
C1—N1—C2—C3	179.9 (2)	C3—C4—C5—C6	0.2 (4)
N1—C2—C3—C4	178.4 (3)	C4—C5—C6—Cl1	179.4 (2)
N1—C2—C3—S1	−2.5 (4)	C4—C5—C6—S1	−0.3 (3)
C6—S1—C3—C4	−0.1 (2)	C3—S1—C6—C5	0.3 (2)
C6—S1—C3—C2	−179.4 (2)	C3—S1—C6—Cl1	−179.49 (17)
C2—C3—C4—C5	179.1 (3)

Cg1 is the centroid of the S3,C3–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—Cl1···Cg1ii	1.714 (3)	3.5182 (14)	3.994 (3)	93.01 (10)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the S3,C3–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—Cl1⋯Cg1i	1.71 (1)	3.52 (1)	3.994 (3)	93 (1)

Symmetry code: (i) .