N,N-Bis(2-thienylmethyl-ene)cyclo-hexane-1,4-diamine.

The title compound, C(16)H(18)N(2)S(2), lies about an inversion center with only half of the mol-ecule in the asymmetric unit. The cyclo-hexane ring adopts a chair conformation, and the terminal thio-phene rings are in a transoid orientation, with an S⋯S separation between the two terminal 2-thio-phene rings of 11.6733 (9) Å.

Related literature

For a general introduction to coordination polymers, see: Batten et al. (2009 ▶); Perry et al. (2009 ▶); Robin & Fromm (2006 ▶). For structurally related compounds, see: Yun et al. (2009 ▶). For related linking ligands containing terminal thio­phene rings, see: Lee & Lee (2007 ▶); Huh et al. (2008 ▶); Kim & Lee (2008 ▶).

Experimental

Crystal data

C16H18N2S2

M = 302.44

Monoclinic,

a = 6.2173 (4) Å

b = 7.4999 (5) Å

c = 17.1289 (12) Å

β = 97.047 (3)°

V = 792.67 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.33 mm−1

T = 296 K

0.46 × 0.24 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.864, T max = 0.937

9045 measured reflections

1889 independent reflections

1590 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.089

S = 1.02

1889 reflections

127 parameters

All H-atom parameters refined

Δρmax = 0.19 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; 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: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809035545/pv2205sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809035545/pv2205Isup2.hkl

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

C16H18N2S2	F(000) = 320
Mr = 302.44	Dx = 1.267 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5365 reflections
a = 6.2173 (4) Å	θ = 2.4–28.2°
b = 7.4999 (5) Å	µ = 0.33 mm−1
c = 17.1289 (12) Å	T = 296 K
β = 97.047 (3)°	Block, colourless
V = 792.67 (9) Å3	0.46 × 0.24 × 0.20 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	1889 independent reflections
Radiation source: sealed tube	1590 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.864, Tmax = 0.937	k = −8→9
9045 measured reflections	l = −22→19

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089	All H-atom parameters refined
S = 1.02	w = 1/[σ2(Fo2) + (0.0484P)2 + 0.1406P] where P = (Fo2 + 2Fc2)/3
1889 reflections	(Δ/σ)max = 0.001
127 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Experimental. IR (KBr, cm-1): 3443 (w), 3103 (w), 2923 (m), 2852 (w), 1626 (s), 1430 (m), 1306 (w), 1210 (m), 1084 (m), 944 (m), 847 (m), 730 (s), 498 (m).

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	0.65706 (5)	0.42717 (5)	0.78995 (2)	0.04947 (14)
N1	0.78346 (18)	0.71526 (15)	0.91441 (7)	0.0458 (3)
C1	0.4495 (3)	0.2897 (2)	0.75469 (10)	0.0554 (4)
C2	0.2791 (3)	0.3032 (2)	0.79591 (10)	0.0575 (4)
C3	0.3138 (2)	0.42688 (19)	0.85814 (9)	0.0488 (3)
C4	0.51420 (19)	0.50601 (18)	0.86246 (7)	0.0396 (3)
C5	0.6024 (2)	0.64140 (18)	0.91770 (7)	0.0412 (3)
C6	0.8511 (2)	0.85271 (18)	0.97279 (8)	0.0430 (3)
C7	0.8308 (3)	1.0366 (2)	0.93470 (10)	0.0527 (4)
C8	1.0844 (2)	0.8189 (2)	1.00708 (10)	0.0516 (3)
H1	0.465 (3)	0.218 (2)	0.7107 (11)	0.069 (5)*
H2	0.157 (3)	0.239 (3)	0.7840 (10)	0.070 (5)*
H3	0.218 (2)	0.4550 (19)	0.8910 (10)	0.051 (4)*
H5	0.518 (2)	0.6691 (19)	0.9570 (9)	0.050 (4)*
H6	0.761 (2)	0.847 (2)	1.0152 (9)	0.053 (4)*
H7A	0.687 (3)	1.058 (2)	0.9140 (12)	0.074 (6)*
H7B	0.909 (3)	1.037 (2)	0.8896 (11)	0.061 (5)*
H8B	1.176 (3)	0.821 (2)	0.9662 (10)	0.056 (4)*
H8A	1.104 (3)	0.705 (2)	1.0311 (10)	0.059 (4)*

	U11	U22	U33	U12	U13	U23
S1	0.0449 (2)	0.0531 (2)	0.0512 (2)	−0.00126 (14)	0.00905 (15)	−0.00792 (15)
N1	0.0473 (6)	0.0465 (6)	0.0443 (6)	−0.0070 (5)	0.0087 (5)	−0.0088 (5)
C1	0.0617 (9)	0.0484 (8)	0.0545 (8)	−0.0023 (7)	0.0005 (7)	−0.0112 (7)
C2	0.0523 (8)	0.0552 (9)	0.0631 (9)	−0.0150 (7)	−0.0003 (7)	−0.0052 (7)
C3	0.0445 (7)	0.0532 (8)	0.0491 (7)	−0.0066 (6)	0.0077 (6)	−0.0008 (6)
C4	0.0400 (6)	0.0389 (6)	0.0393 (6)	0.0006 (5)	0.0035 (5)	0.0025 (5)
C5	0.0418 (6)	0.0428 (7)	0.0389 (6)	0.0016 (5)	0.0051 (5)	0.0000 (5)
C6	0.0450 (7)	0.0441 (7)	0.0407 (6)	−0.0041 (5)	0.0084 (5)	−0.0076 (6)
C7	0.0531 (8)	0.0492 (8)	0.0518 (8)	0.0023 (6)	−0.0091 (7)	−0.0035 (6)
C8	0.0544 (8)	0.0397 (8)	0.0584 (9)	0.0050 (6)	−0.0030 (7)	−0.0044 (6)

S1—C1	1.7038 (16)	C5—H5	0.928 (15)
S1—C4	1.7181 (13)	C6—C8	1.518 (2)
N1—C5	1.2619 (16)	C6—C7	1.524 (2)
N1—C6	1.4616 (16)	C6—H6	0.971 (16)
C1—C2	1.347 (2)	C7—C8i	1.522 (2)
C1—H1	0.941 (18)	C7—H7A	0.94 (2)
C2—C3	1.410 (2)	C7—H7B	0.960 (19)
C2—H2	0.900 (18)	C8—C7i	1.522 (2)
C3—C4	1.3736 (18)	C8—H8B	0.954 (16)
C3—H3	0.894 (15)	C8—H8A	0.951 (17)
C4—C5	1.4492 (19)
C1—S1—C4	91.62 (7)	N1—C6—C7	110.09 (11)
C5—N1—C6	117.53 (11)	C8—C6—C7	109.96 (12)
C2—C1—S1	112.26 (12)	N1—C6—H6	109.6 (9)
C2—C1—H1	129.0 (11)	C8—C6—H6	108.2 (9)
S1—C1—H1	118.7 (11)	C7—C6—H6	109.8 (9)
C1—C2—C3	112.85 (14)	C8i—C7—C6	111.09 (12)
C1—C2—H2	122.3 (11)	C8i—C7—H7A	111.4 (11)
C3—C2—H2	124.8 (11)	C6—C7—H7A	110.0 (11)
C4—C3—C2	112.27 (13)	C8i—C7—H7B	111.0 (11)
C4—C3—H3	122.4 (10)	C6—C7—H7B	108.7 (10)
C2—C3—H3	125.3 (10)	H7A—C7—H7B	104.5 (15)
C3—C4—C5	127.31 (12)	C6—C8—C7i	111.86 (12)
C3—C4—S1	110.99 (11)	C6—C8—H8B	109.9 (10)
C5—C4—S1	121.69 (9)	C7i—C8—H8B	106.4 (10)
N1—C5—C4	123.14 (12)	C6—C8—H8A	112.4 (10)
N1—C5—H5	121.5 (10)	C7i—C8—H8A	110.0 (10)
C4—C5—H5	115.3 (10)	H8B—C8—H8A	106.0 (13)
N1—C6—C8	109.16 (11)