Thio-phene-2-carbaldehyde azine.

The asymmetric unit of the title compound, C10H8N2S2, is composed of two independent half-mol-ecules, each residing on a center of symmetry. In the crystal, weak C-H⋯π inter-actions join the two symmetry-independent molecules together into interlinked chains parallel to [011]. The crystal structure was refined as a two-component pseudo-merohedral twin using the twin law 001 0-10 100. The refined domain fractions are 0.516 (3) and 0.484 (3).

Related literature

For the structure of pyridine-4-carbaldehyde, see: Shanmuga Sundara Raj et al. (2000 ▶) and for the structure of (E)-1-di­phenyl­methyl­idene-2-[(1H-indol-3-yl)methyl­idene]hydrazine, see: Archana et al. (2010 ▶).

Experimental

Crystal data

C10H8N2S2

M = 220.30

Monoclinic,

a = 9.681 (2) Å

b = 11.399 (3) Å

c = 9.694 (2) Å

β = 100.850 (9)°

V = 1050.6 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.47 mm−1

T = 200 K

0.50 × 0.20 × 0.20 mm

Data collection

Bruker SMART X2S CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2010 ▶) T min = 0.69, T max = 0.91

7000 measured reflections

1890 independent reflections

1349 reflections with I > 2σ(I)

R int = 0.073

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.156

S = 0.99

1890 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.61 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813013275/zp2003sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813013275/zp2003Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813013275/zp2003Isup3.mol

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813013275/zp2003Isup4.cml

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

C10H8N2S2	Dx = 1.393 Mg m−3
Mr = 220.30	Melting point: 420 K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.681 (2) Å	Cell parameters from 1222 reflections
b = 11.399 (3) Å	θ = 2.8–21.5°
c = 9.694 (2) Å	µ = 0.47 mm−1
β = 100.850 (9)°	T = 200 K
V = 1050.6 (5) Å3	Prism, yellow
Z = 4	0.50 × 0.20 × 0.20 mm
F(000) = 456

Bruker SMART X2S CCD diffractometer	1890 independent reflections
Radiation source: XOS X-beam microfocus source	1349 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.073
Detector resolution: 8.3330 pixels mm-1	θmax = 25.4°, θmin = 1.8°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2010)	k = −12→13
Tmin = 0.69, Tmax = 0.91	l = −11→11
7000 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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0825P)2] where P = (Fo2 + 2Fc2)/3
1890 reflections	(Δ/σ)max < 0.001
128 parameters	Δρmax = 0.61 e Å−3
0 restraints	Δρmin = −0.28 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	−0.15035 (15)	0.24362 (18)	−0.24483 (16)	0.0462 (4)
S2	−0.25404 (15)	0.26513 (11)	0.35231 (15)	0.0486 (5)
N1	−0.0295 (4)	0.0438 (3)	−0.0474 (4)	0.0442 (12)
N2	−0.0495 (4)	0.4567 (3)	0.4718 (4)	0.0446 (13)
C1	−0.0425 (5)	0.1418 (4)	0.0133 (5)	0.0432 (14)
H1	−0.0153	0.147	0.1125	0.052*
C2	−0.0969 (5)	0.2439 (3)	−0.0643 (6)	0.0361 (13)
C3	−0.1093 (6)	0.3536 (4)	−0.0119 (6)	0.0484 (14)
H3	−0.084	0.3726	0.085	0.058*
C4	−0.1644 (5)	0.4370 (4)	−0.1182 (6)	0.0540 (15)
H4	−0.1815	0.5171	−0.1002	0.065*
C5	−0.1889 (6)	0.3885 (4)	−0.2458 (6)	0.0519 (15)
H5	−0.2244	0.4312	−0.3291	0.062*
C6	0.0080 (5)	0.3572 (4)	0.4585 (5)	0.0395 (13)
H6	0.1073	0.35	0.4843	0.047*
C7	−0.0737 (5)	0.2566 (4)	0.4056 (5)	0.0340 (13)
C8	−0.0274 (6)	0.1447 (4)	0.3957 (6)	0.0505 (15)
H8	0.0683	0.122	0.4225	0.061*
C9	−0.1364 (6)	0.0664 (4)	0.3416 (5)	0.0572 (16)
H9	−0.1225	−0.0147	0.3265	0.069*
C10	−0.2655 (6)	0.1210 (4)	0.3131 (6)	0.0570 (16)
H10	−0.3511	0.082	0.2757	0.068*

	U11	U22	U33	U12	U13	U23
S1	0.0523 (12)	0.0503 (7)	0.0336 (10)	−0.0004 (5)	0.0017 (7)	0.0045 (5)
S2	0.0389 (11)	0.0509 (7)	0.0543 (13)	−0.0039 (6)	0.0041 (7)	0.0047 (6)
N1	0.048 (3)	0.039 (2)	0.043 (3)	−0.0068 (19)	0.002 (2)	0.0083 (19)
N2	0.040 (3)	0.040 (2)	0.053 (3)	−0.0068 (17)	0.009 (2)	0.0027 (19)
C1	0.055 (4)	0.039 (2)	0.037 (3)	−0.008 (2)	0.015 (3)	0.003 (2)
C2	0.028 (3)	0.044 (2)	0.037 (3)	−0.0046 (19)	0.007 (2)	0.004 (2)
C3	0.055 (4)	0.045 (2)	0.047 (3)	0.000 (3)	0.017 (3)	0.001 (3)
C4	0.047 (4)	0.041 (3)	0.075 (4)	−0.001 (2)	0.016 (3)	0.002 (3)
C5	0.041 (3)	0.053 (3)	0.061 (4)	0.004 (2)	0.007 (3)	0.015 (3)
C6	0.037 (3)	0.042 (3)	0.041 (3)	0.001 (2)	0.010 (2)	0.001 (2)
C7	0.030 (3)	0.041 (2)	0.032 (3)	0.0031 (19)	0.010 (2)	0.005 (2)
C8	0.045 (3)	0.046 (3)	0.065 (4)	0.002 (2)	0.022 (3)	−0.002 (3)
C9	0.083 (5)	0.040 (3)	0.054 (4)	−0.004 (3)	0.026 (3)	−0.004 (2)
C10	0.071 (4)	0.051 (3)	0.048 (4)	−0.027 (3)	0.007 (3)	0.000 (3)

S1—C5	1.693 (5)	C3—H3	0.95
S1—C2	1.729 (6)	C4—C5	1.335 (7)
S2—C10	1.685 (5)	C4—H4	0.95
S2—C7	1.728 (5)	C5—H5	0.95
N1—C1	1.280 (5)	C6—C7	1.432 (6)
N1—N1i	1.402 (7)	C6—H6	0.95
N2—C6	1.281 (5)	C7—C8	1.361 (6)
N2—N2ii	1.412 (7)	C8—C9	1.406 (7)
C1—C2	1.431 (6)	C8—H8	0.95
C1—H1	0.95	C9—C10	1.377 (7)
C2—C3	1.364 (6)	C9—H9	0.95
C3—C4	1.429 (7)	C10—H10	0.95
C5—S1—C2	91.6 (3)	C4—C5—H5	123.3
C10—S2—C7	91.9 (3)	S1—C5—H5	123.3
C1—N1—N1i	112.6 (5)	N2—C6—C7	121.6 (5)
C6—N2—N2ii	112.5 (5)	N2—C6—H6	119.2
N1—C1—C2	121.8 (5)	C7—C6—H6	119.2
N1—C1—H1	119.1	C8—C7—C6	127.5 (5)
C2—C1—H1	119.1	C8—C7—S2	111.1 (4)
C3—C2—C1	126.8 (5)	C6—C7—S2	121.4 (3)
C3—C2—S1	110.4 (4)	C7—C8—C9	112.8 (5)
C1—C2—S1	122.7 (3)	C7—C8—H8	123.6
C2—C3—C4	112.9 (5)	C9—C8—H8	123.6
C2—C3—H3	123.6	C10—C9—C8	112.2 (5)
C4—C3—H3	123.6	C10—C9—H9	123.9
C5—C4—C3	111.7 (5)	C8—C9—H9	123.9
C5—C4—H4	124.1	C9—C10—S2	112.1 (4)
C3—C4—H4	124.1	C9—C10—H10	124.0
C4—C5—S1	113.5 (4)	S2—C10—H10	124.0

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···C8	0.95	2.77	3.683 (7)	161
C1—H1···C9	0.95	2.85	3.576 (7)	134
C8—H8···C4iii	0.95	2.77	3.663 (7)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯C8	0.95	2.77	3.683 (7)	161
C1—H1⋯C9	0.95	2.85	3.576 (7)	134
C8—H8⋯C4i	0.95	2.77	3.663 (7)	156

Symmetry code: (i) .