N,N'-Bis[(E)-(3-methyl-2-thienyl)methyl-idene]ethane-1,2-diamine.

Two independent half-mol-ecules, each being completed by inversion symmetry, comprise the asymmetric unit of the title compound, C(14)H(16)N(2)S(2). The major difference between the mol-ecules is found in the central C-C bond [the C-N-C-C torsion angles are 114.66 (18) and 128.94 (18)° in the two mol-ecules]. The thio-phene and imine groups are almost co-planar in each case [S-C-C-N torsion angles = -6.9 (2) and -3.6 (2)°]. In the crystal, the mol-ecules aggregate into supra-molecular chains via C-H⋯π inter-actions.

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 ▶).

Experimental

Crystal data

C14H16N2S2

M = 276.41

Triclinic,

a = 8.7610 (6) Å

b = 8.9502 (6) Å

c = 8.9853 (6) Å

α = 92.760 (1)°

β = 91.653 (1)°

γ = 106.066 (1)°

V = 675.61 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.38 mm−1

T = 100 K

0.30 × 0.30 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.797, T max = 0.862

6435 measured reflections

3089 independent reflections

2822 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.100

S = 1.10

3089 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.27 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 general, I. DOI: 10.1107/S1600536810041632/pk2279sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041632/pk2279Isup2.hkl

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

C14H16N2S2	Z = 2
Mr = 276.41	F(000) = 292
Triclinic, P1	Dx = 1.359 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7610 (6) Å	Cell parameters from 4410 reflections
b = 8.9502 (6) Å	θ = 4.3–28.3°
c = 8.9853 (6) Å	µ = 0.38 mm−1
α = 92.760 (1)°	T = 100 K
β = 91.653 (1)°	Prism, colourless
γ = 106.066 (1)°	0.30 × 0.30 × 0.10 mm
V = 675.61 (8) Å3

Bruker SMART APEX diffractometer	3089 independent reflections
Radiation source: fine-focus sealed tube	2822 reflections with I > 2σ(I)
graphite	Rint = 0.019
ω scans	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.797, Tmax = 0.862	k = −11→10
6435 measured reflections	l = −11→11

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0508P)2 + 0.4238P] where P = (Fo2 + 2Fc2)/3
3089 reflections	(Δ/σ)max < 0.001
165 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.47805 (4)	0.72178 (4)	0.45069 (4)	0.01583 (12)
N1	0.48699 (16)	0.93243 (16)	0.19349 (14)	0.0171 (3)
C1	0.47949 (19)	1.03494 (19)	0.07326 (17)	0.0170 (3)
H1A	0.5554	1.1387	0.0968	0.020*
H1B	0.3712	1.0483	0.0637	0.020*
C2	0.59455 (18)	0.98652 (18)	0.29593 (17)	0.0151 (3)
H2	0.6641	1.0881	0.2890	0.018*
C3	0.61453 (18)	0.89825 (18)	0.42300 (17)	0.0147 (3)
C4	0.73245 (18)	0.93799 (18)	0.53428 (17)	0.0157 (3)
C5	0.7128 (2)	0.82044 (19)	0.63988 (17)	0.0174 (3)
H5	0.7844	0.8264	0.7228	0.021*
C6	0.5808 (2)	0.69924 (19)	0.60906 (17)	0.0180 (3)
H6	0.5493	0.6120	0.6686	0.022*
C7	0.8608 (2)	1.0898 (2)	0.5493 (2)	0.0223 (3)
H7A	0.8213	1.1682	0.6035	0.033*
H7B	0.8913	1.1247	0.4500	0.033*
H7C	0.9535	1.0756	0.6043	0.033*
S2	0.08033 (5)	0.56857 (5)	0.69562 (4)	0.01757 (12)
N2	0.01928 (16)	0.80946 (15)	0.92178 (15)	0.0166 (3)
C8	−0.0229 (2)	0.91842 (18)	1.02823 (18)	0.0179 (3)
H8A	0.0328	0.9189	1.1257	0.021*
H8B	−0.1388	0.8846	1.0427	0.021*
C9	0.09982 (18)	0.72358 (18)	0.97335 (17)	0.0151 (3)
H9	0.1320	0.7369	1.0761	0.018*
C10	0.14457 (18)	0.60595 (17)	0.88127 (17)	0.0138 (3)
C11	0.23606 (18)	0.51136 (18)	0.92386 (17)	0.0147 (3)
C12	0.25375 (19)	0.40900 (18)	0.80306 (18)	0.0177 (3)
H12	0.3134	0.3356	0.8116	0.021*
C13	0.1767 (2)	0.42700 (19)	0.67441 (19)	0.0196 (3)
H13	0.1764	0.3680	0.5836	0.023*
C14	0.30760 (19)	0.5131 (2)	1.07776 (18)	0.0191 (3)
H14A	0.3663	0.6200	1.1108	0.029*
H14B	0.3803	0.4473	1.0766	0.029*
H14C	0.2229	0.4731	1.1464	0.029*

	U11	U22	U33	U12	U13	U23
S1	0.0184 (2)	0.01340 (19)	0.0147 (2)	0.00282 (14)	0.00089 (14)	0.00138 (14)
N1	0.0216 (7)	0.0169 (6)	0.0123 (6)	0.0044 (5)	0.0017 (5)	0.0028 (5)
C1	0.0196 (7)	0.0176 (7)	0.0136 (7)	0.0046 (6)	0.0003 (6)	0.0034 (6)
C2	0.0176 (7)	0.0133 (7)	0.0152 (7)	0.0054 (6)	0.0039 (6)	0.0008 (5)
C3	0.0172 (7)	0.0130 (7)	0.0142 (7)	0.0045 (6)	0.0029 (6)	0.0009 (5)
C4	0.0185 (7)	0.0146 (7)	0.0149 (7)	0.0061 (6)	0.0014 (6)	0.0001 (6)
C5	0.0229 (8)	0.0178 (7)	0.0133 (7)	0.0090 (6)	−0.0003 (6)	0.0006 (6)
C6	0.0250 (8)	0.0171 (7)	0.0140 (7)	0.0087 (6)	0.0034 (6)	0.0031 (6)
C7	0.0213 (8)	0.0178 (8)	0.0256 (8)	0.0024 (6)	−0.0047 (6)	0.0022 (6)
S2	0.0210 (2)	0.0169 (2)	0.0142 (2)	0.00442 (15)	−0.00034 (14)	0.00084 (14)
N2	0.0193 (6)	0.0113 (6)	0.0188 (6)	0.0040 (5)	−0.0001 (5)	−0.0004 (5)
C8	0.0230 (8)	0.0132 (8)	0.0187 (7)	0.0068 (6)	0.0021 (6)	0.0007 (6)
C9	0.0148 (7)	0.0129 (7)	0.0159 (7)	0.0010 (5)	0.0007 (5)	0.0015 (6)
C10	0.0148 (7)	0.0115 (7)	0.0144 (7)	0.0022 (5)	0.0018 (5)	0.0012 (5)
C11	0.0134 (7)	0.0138 (7)	0.0160 (7)	0.0017 (5)	0.0032 (5)	0.0024 (6)
C12	0.0163 (7)	0.0141 (7)	0.0225 (8)	0.0034 (6)	0.0059 (6)	0.0011 (6)
C13	0.0214 (8)	0.0158 (7)	0.0199 (8)	0.0026 (6)	0.0061 (6)	−0.0026 (6)
C14	0.0171 (7)	0.0228 (8)	0.0186 (8)	0.0069 (6)	−0.0005 (6)	0.0034 (6)

S1—C6	1.7119 (16)	S2—C13	1.7125 (17)
S1—C3	1.7309 (16)	S2—C10	1.7318 (16)
N1—C2	1.274 (2)	N2—C9	1.272 (2)
N1—C1	1.4621 (19)	N2—C8	1.460 (2)
C1—C1i	1.525 (3)	C8—C8ii	1.520 (3)
C1—H1A	0.9900	C8—H8A	0.9900
C1—H1B	0.9900	C8—H8B	0.9900
C2—C3	1.453 (2)	C9—C10	1.453 (2)
C2—H2	0.9500	C9—H9	0.9500
C3—C4	1.377 (2)	C10—C11	1.377 (2)
C4—C5	1.429 (2)	C11—C12	1.426 (2)
C4—C7	1.502 (2)	C11—C14	1.499 (2)
C5—C6	1.360 (2)	C12—C13	1.361 (2)
C5—H5	0.9500	C12—H12	0.9500
C6—H6	0.9500	C13—H13	0.9500
C7—H7A	0.9800	C14—H14A	0.9800
C7—H7B	0.9800	C14—H14B	0.9800
C7—H7C	0.9800	C14—H14C	0.9800
C6—S1—C3	91.47 (8)	C13—S2—C10	91.55 (8)
C2—N1—C1	116.35 (13)	C9—N2—C8	116.78 (14)
N1—C1—C1i	109.83 (16)	N2—C8—C8ii	110.34 (17)
N1—C1—H1A	109.7	N2—C8—H8A	109.6
C1i—C1—H1A	109.7	C8ii—C8—H8A	109.6
N1—C1—H1B	109.7	N2—C8—H8B	109.6
C1i—C1—H1B	109.7	C8ii—C8—H8B	109.6
H1A—C1—H1B	108.2	H8A—C8—H8B	108.1
N1—C2—C3	122.28 (14)	N2—C9—C10	122.61 (14)
N1—C2—H2	118.9	N2—C9—H9	118.7
C3—C2—H2	118.9	C10—C9—H9	118.7
C4—C3—C2	127.93 (14)	C11—C10—C9	127.42 (14)
C4—C3—S1	111.67 (12)	C11—C10—S2	111.68 (12)
C2—C3—S1	120.39 (12)	C9—C10—S2	120.89 (11)
C3—C4—C5	111.63 (14)	C10—C11—C12	111.52 (14)
C3—C4—C7	124.67 (14)	C10—C11—C14	124.84 (14)
C5—C4—C7	123.60 (14)	C12—C11—C14	123.64 (14)
C6—C5—C4	112.87 (14)	C13—C12—C11	113.24 (14)
C6—C5—H5	123.6	C13—C12—H12	123.4
C4—C5—H5	123.6	C11—C12—H12	123.4
C5—C6—S1	112.33 (12)	C12—C13—S2	112.00 (12)
C5—C6—H6	123.8	C12—C13—H13	124.0
S1—C6—H6	123.8	S2—C13—H13	124.0
C4—C7—H7A	109.5	C11—C14—H14A	109.5
C4—C7—H7B	109.5	C11—C14—H14B	109.5
H7A—C7—H7B	109.5	H14A—C14—H14B	109.5
C4—C7—H7C	109.5	C11—C14—H14C	109.5
H7A—C7—H7C	109.5	H14A—C14—H14C	109.5
H7B—C7—H7C	109.5	H14B—C14—H14C	109.5
C2—N1—C1—C1i	114.66 (18)	C9—N2—C8—C8ii	128.94 (18)
C1—N1—C2—C3	179.26 (14)	C8—N2—C9—C10	177.52 (14)
N1—C2—C3—C4	174.57 (16)	N2—C9—C10—C11	177.29 (16)
N1—C2—C3—S1	−6.9 (2)	N2—C9—C10—S2	−3.6 (2)
C6—S1—C3—C4	−1.13 (13)	C13—S2—C10—C11	−0.31 (12)
C6—S1—C3—C2	−179.90 (13)	C13—S2—C10—C9	−179.53 (13)
C2—C3—C4—C5	−179.55 (15)	C9—C10—C11—C12	179.52 (15)
S1—C3—C4—C5	1.80 (17)	S2—C10—C11—C12	0.36 (17)
C2—C3—C4—C7	3.9 (3)	C9—C10—C11—C14	0.1 (3)
S1—C3—C4—C7	−174.74 (13)	S2—C10—C11—C14	−179.05 (12)
C3—C4—C5—C6	−1.7 (2)	C10—C11—C12—C13	−0.2 (2)
C7—C4—C5—C6	174.86 (15)	C14—C11—C12—C13	179.18 (14)
C4—C5—C6—S1	0.86 (18)	C11—C12—C13—S2	0.01 (18)
C3—S1—C6—C5	0.14 (13)	C10—S2—C13—C12	0.17 (13)

Cg1 is the centroid of the S1,C3–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···Cg1iii	0.95	2.89	3.6179 (19)	134

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the S1,C3–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯Cg1i	0.95	2.89	3.6179 (19)	134

Symmetry code: (i) .