N,N'-Bis[(E)-1-(thio-phen-3-yl)ethyl-idene]ethane-1,2-diamine.

The complete mol-ecule of the title compound, C(14)H(16)N(2)S(2), is generated by a crystallographic inversion centre. The thio-phene residue is close to being coplanar with the imine group [C-C-C-N torsion angle = 6.5 (2)°], and the conformation about the imine C=N bond [1.281 (2) Å] is E. In the crystal, the three-dimensional architecture is consolidated by C-H⋯N, C-H⋯π and S⋯S [3.3932 (7) Å] inter-actions.

Related literature

For background to 2-substituted thio­phenes, see: Kleemann et al. (2006 ▶). For related structures, see: Prasath et al. (2010a ▶,b ▶).

Experimental

Crystal data

C14H16N2S2

M = 276.41

Monoclinic,

a = 7.5231 (6) Å

b = 11.2338 (6) Å

c = 8.5967 (6) Å

β = 112.894 (9)°

V = 669.30 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.38 mm−1

T = 100 K

0.20 × 0.15 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.928, T max = 0.963

2789 measured reflections

1542 independent reflections

1339 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.105

S = 1.06

1542 reflections

83 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.41 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 datablock(s) global, I. DOI: 10.1107/S1600536812009798/hb6669sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812009798/hb6669Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812009798/hb6669Isup3.cml

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

C14H16N2S2	F(000) = 292
Mr = 276.41	Dx = 1.372 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1637 reflections
a = 7.5231 (6) Å	θ = 2.6–27.5°
b = 11.2338 (6) Å	µ = 0.38 mm−1
c = 8.5967 (6) Å	T = 100 K
β = 112.894 (9)°	Prism, colourless
V = 669.30 (8) Å3	0.20 × 0.15 × 0.10 mm
Z = 2

Agilent SuperNova Dual diffractometer with an Atlas detector	1542 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1339 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.033
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.9°
ω scan	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −14→9
Tmin = 0.928, Tmax = 0.963	l = −11→7
2789 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0482P)2 + 0.3751P] where P = (Fo2 + 2Fc2)/3
1542 reflections	(Δ/σ)max = 0.001
83 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.41 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
S1	0.88734 (7)	0.59544 (4)	0.83858 (6)	0.01735 (17)
N1	0.6122 (2)	0.51740 (13)	0.23310 (18)	0.0129 (3)
C1	0.7443 (3)	0.69397 (16)	0.6897 (2)	0.0161 (4)
H1	0.7138	0.7719	0.7143	0.019*
C2	0.6805 (3)	0.64614 (16)	0.5325 (2)	0.0138 (4)
H2	0.5985	0.6872	0.4342	0.017*
C3	0.7493 (2)	0.52741 (15)	0.5294 (2)	0.0127 (4)
C4	0.8632 (3)	0.48878 (16)	0.6889 (2)	0.0151 (4)
H4	0.9214	0.4123	0.7133	0.018*
C5	0.7023 (2)	0.45986 (15)	0.3700 (2)	0.0121 (4)
C6	0.7668 (3)	0.33137 (16)	0.3829 (2)	0.0156 (4)
H6A	0.6939	0.2903	0.2764	0.023*
H6B	0.7435	0.2923	0.4751	0.023*
H6C	0.9049	0.3283	0.4055	0.023*
C7	0.5591 (3)	0.45805 (16)	0.0702 (2)	0.0144 (4)
H7A	0.4831	0.3856	0.0675	0.017*
H7B	0.6771	0.4338	0.0537	0.017*

	U11	U22	U33	U12	U13	U23
S1	0.0200 (3)	0.0185 (3)	0.0112 (3)	0.00100 (18)	0.00349 (19)	−0.00088 (17)
N1	0.0144 (8)	0.0129 (7)	0.0110 (7)	−0.0001 (6)	0.0043 (6)	−0.0005 (6)
C1	0.0183 (9)	0.0150 (8)	0.0170 (9)	0.0011 (7)	0.0091 (7)	0.0012 (7)
C2	0.0147 (9)	0.0151 (9)	0.0128 (8)	0.0013 (7)	0.0065 (7)	0.0023 (7)
C3	0.0124 (8)	0.0129 (8)	0.0134 (9)	−0.0012 (7)	0.0057 (7)	0.0010 (7)
C4	0.0171 (9)	0.0137 (8)	0.0136 (9)	0.0003 (7)	0.0052 (7)	0.0001 (7)
C5	0.0101 (8)	0.0123 (8)	0.0146 (9)	−0.0011 (6)	0.0055 (7)	−0.0006 (7)
C6	0.0184 (9)	0.0125 (8)	0.0158 (9)	0.0020 (7)	0.0064 (7)	0.0004 (7)
C7	0.0177 (9)	0.0124 (8)	0.0121 (9)	0.0005 (7)	0.0047 (7)	−0.0024 (7)

S1—C4	1.7154 (18)	C3—C5	1.484 (2)
S1—C1	1.7174 (19)	C4—H4	0.9500
N1—C5	1.281 (2)	C5—C6	1.513 (2)
N1—C7	1.460 (2)	C6—H6A	0.9800
C1—C2	1.357 (2)	C6—H6B	0.9800
C1—H1	0.9500	C6—H6C	0.9800
C2—C3	1.435 (2)	C7—C7i	1.517 (3)
C2—H2	0.9500	C7—H7A	0.9900
C3—C4	1.374 (2)	C7—H7B	0.9900
C4—S1—C1	92.19 (9)	N1—C5—C6	126.06 (15)
C5—N1—C7	120.01 (15)	C3—C5—C6	117.77 (15)
C2—C1—S1	111.31 (14)	C5—C6—H6A	109.5
C2—C1—H1	124.3	C5—C6—H6B	109.5
S1—C1—H1	124.3	H6A—C6—H6B	109.5
C1—C2—C3	113.35 (16)	C5—C6—H6C	109.5
C1—C2—H2	123.3	H6A—C6—H6C	109.5
C3—C2—H2	123.3	H6B—C6—H6C	109.5
C4—C3—C2	111.37 (16)	N1—C7—C7i	109.65 (18)
C4—C3—C5	126.30 (16)	N1—C7—H7A	109.7
C2—C3—C5	122.32 (15)	C7i—C7—H7A	109.7
C3—C4—S1	111.78 (14)	N1—C7—H7B	109.7
C3—C4—H4	124.1	C7i—C7—H7B	109.7
S1—C4—H4	124.1	H7A—C7—H7B	108.2
N1—C5—C3	116.16 (15)
C4—S1—C1—C2	0.34 (14)	C7—N1—C5—C3	−179.72 (15)
S1—C1—C2—C3	−0.7 (2)	C7—N1—C5—C6	1.3 (3)
C1—C2—C3—C4	0.8 (2)	C4—C3—C5—N1	−172.11 (17)
C1—C2—C3—C5	−177.97 (16)	C2—C3—C5—N1	6.5 (2)
C2—C3—C4—S1	−0.6 (2)	C4—C3—C5—C6	7.0 (3)
C5—C3—C4—S1	178.19 (14)	C2—C3—C5—C6	−174.39 (15)
C1—S1—C4—C3	0.13 (15)	C5—N1—C7—C7i	175.58 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···N1ii	0.95	2.51	3.454 (2)	172
C6—H6C···Cg1iii	0.98	2.74	3.624 (2)	150

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the S1,C1–C4 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯N1i	0.95	2.51	3.454 (2)	172
C6—H6C⋯Cg1ii	0.98	2.74	3.624 (2)	150

Symmetry codes: (i) ; (ii) .