N,N'-Bis(2-thienylmethyl-ene)benzene-1,4-diamine.

The Schiff base, C(16)H(12)N(2)S(2), has been synthesized by refluxing an ethano-lic solution of thio-phene-2-carbaldehyde and benzene-1,4-diamine. The center of the benzene ring is located on a crystallographic center of inversion. The dihedral angle between the benzene and thio-phene rings is 63.6 (1)°.

Related literature

For general background to Schiff base complexes, see: Andersen et al. (2005 ▶); Koizumi et al. (2005 ▶); Boskovic et al. (2003 ▶); Oshio et al. (2005 ▶). For the synthesis, see: Kannappan et al. (2005 ▶).

Experimental

Crystal data

C16H12N2S2

M = 296.40

Monoclinic,

a = 6.1882 (7) Å

b = 7.2371 (9) Å

c = 16.375 (2) Å

β = 95.860 (2)°

V = 729.5 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.36 mm−1

T = 294 K

0.15 × 0.11 × 0.09 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.949, T max = 0.969

3380 measured reflections

1252 independent reflections

1021 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.196

S = 1.00

1252 reflections

91 parameters

H-atom parameters not refined

Δρmax = 1.07 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2002 ▶); cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809031869/im2135sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809031869/im2135Isup2.hkl

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

C16H12N2S2	F(000) = 308
Mr = 296.40	Dx = 1.349 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1252 reflections
a = 6.1882 (7) Å	θ = 3.1–25.0°
b = 7.2371 (9) Å	µ = 0.36 mm−1
c = 16.375 (2) Å	T = 294 K
β = 95.860 (2)°	Block, yellow
V = 729.5 (2) Å3	0.15 × 0.11 × 0.09 mm
Z = 2

Bruker APEXII CCD area-detector diffractometer	1252 independent reflections
Radiation source: fine-focus sealed tube	1021 reflections with I > 2σ(I)
graphite	Rint = 0.019
φ and ω scans	θmax = 25.0°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −7→7
Tmin = 0.949, Tmax = 0.969	k = −8→8
3380 measured reflections	l = −19→10

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.196	H-atom parameters not refined
S = 1.00	w = 1/[σ2(Fo2) + (0.141P)2 + 0.3146P] where P = (Fo2 + 2Fc2)/3
1252 reflections	(Δ/σ)max < 0.001
91 parameters	Δρmax = 1.07 e Å−3
0 restraints	Δρmin = −0.21 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	0.15131 (14)	−0.10612 (13)	0.29041 (6)	0.0619 (5)
N1	0.3196 (4)	0.1917 (4)	0.41314 (16)	0.0486 (7)
C1	0.0201 (5)	0.0013 (4)	0.36497 (18)	0.0462 (7)
C2	−0.1804 (5)	−0.0755 (5)	0.3705 (2)	0.0565 (9)
H2	−0.2774	−0.0333	0.4061	0.068*
C3	−0.2234 (6)	−0.2258 (5)	0.3163 (3)	0.0664 (10)
H3	−0.3489	−0.2972	0.3136	0.080*
C4	−0.0594 (6)	−0.2534 (6)	0.2685 (3)	0.0707 (11)
H4	−0.0624	−0.3437	0.2280	0.085*
C5	0.1188 (5)	0.1553 (4)	0.41151 (18)	0.0456 (7)
H5	0.0321	0.2297	0.4411	0.055*
C6	0.4043 (5)	0.3492 (4)	0.45720 (17)	0.0422 (7)
C7	0.3093 (5)	0.5209 (5)	0.4490 (2)	0.0564 (9)
H7	0.1820	0.5361	0.4142	0.068*
C8	0.6000 (6)	0.3299 (5)	0.5086 (2)	0.0576 (9)
H8	0.6681	0.2153	0.5138	0.069*

	U11	U22	U33	U12	U13	U23
S1	0.0552 (6)	0.0657 (7)	0.0656 (7)	−0.0030 (4)	0.0105 (4)	−0.0170 (4)
N1	0.0464 (15)	0.0470 (15)	0.0525 (15)	−0.0058 (11)	0.0059 (11)	−0.0114 (12)
C1	0.0453 (16)	0.0484 (17)	0.0436 (15)	0.0007 (12)	−0.0013 (12)	−0.0027 (13)
C2	0.0483 (18)	0.062 (2)	0.059 (2)	−0.0059 (15)	0.0054 (15)	−0.0085 (16)
C3	0.0528 (19)	0.061 (2)	0.083 (3)	−0.0100 (16)	−0.0059 (18)	−0.0154 (19)
C4	0.068 (2)	0.063 (2)	0.079 (2)	−0.0017 (18)	−0.0038 (19)	−0.0248 (19)
C5	0.0500 (17)	0.0447 (16)	0.0424 (16)	0.0006 (13)	0.0052 (13)	−0.0041 (12)
C6	0.0422 (16)	0.0427 (15)	0.0417 (15)	−0.0024 (11)	0.0046 (12)	−0.0051 (12)
C7	0.0480 (17)	0.0531 (19)	0.065 (2)	0.0017 (14)	−0.0066 (15)	−0.0032 (16)
C8	0.055 (2)	0.0484 (18)	0.068 (2)	0.0073 (14)	−0.0004 (16)	−0.0039 (16)

S1—C4	1.694 (4)	C3—H3	0.9300
S1—C1	1.719 (3)	C4—H4	0.9300
N1—C5	1.268 (4)	C5—H5	0.9300
N1—C6	1.421 (4)	C6—C7	1.375 (4)
C1—C2	1.371 (4)	C6—C8	1.410 (4)
C1—C5	1.449 (4)	C7—C8i	1.373 (5)
C2—C3	1.412 (5)	C7—H7	0.9300
C2—H2	0.9300	C8—C7i	1.373 (5)
C3—C4	1.358 (6)	C8—H8	0.9300
C4—S1—C1	91.48 (17)	S1—C4—H4	123.5
C5—N1—C6	119.1 (3)	N1—C5—C1	122.0 (3)
C2—C1—C5	127.8 (3)	N1—C5—H5	119.0
C2—C1—S1	111.1 (2)	C1—C5—H5	119.0
C5—C1—S1	121.1 (2)	C7—C6—C8	118.8 (3)
C1—C2—C3	112.6 (3)	C7—C6—N1	122.9 (3)
C1—C2—H2	123.7	C8—C6—N1	118.2 (3)
C3—C2—H2	123.7	C8i—C7—C6	120.8 (3)
C4—C3—C2	111.8 (3)	C8i—C7—H7	119.6
C4—C3—H3	124.1	C6—C7—H7	119.6
C2—C3—H3	124.1	C7i—C8—C6	120.4 (3)
C3—C4—S1	113.0 (3)	C7i—C8—H8	119.8
C3—C4—H4	123.5	C6—C8—H8	119.8