(E)-5-Phenyl-N-(2-thienylmethyl-ene)-1,3,4-thia-diazole-2-amine.

In the title compound, C(13)H(9)N(3)S(2), the thio-phene and phenyl rings are oriented at dihedral angles of 8.00 (7) and 6.31 (7)°, respectively, with respect to the central thia-diazole ring. No significant C-H⋯S and π-π inter-actions exist in the crystal structure.

Related literature

For the biological activity of [1,3,4]-thia­diazole-containing compounds, see: Foroumadi, Soltani et al. (2003 ▶); Foroumadi, Mansouri et al. (2003 ▶); Holla et al. (2002 ▶); Genc & Servi (2005 ▶); Servi et al. (2005 ▶). For a related structure, see: Dege et al. (2006 ▶).

Experimental

Crystal data

C13H9N3S2

M = 271.35

Monoclinic,

a = 6.2238 (3) Å

b = 7.7393 (3) Å

c = 25.6959 (13) Å

β = 94.701 (4)°

V = 1233.55 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.41 mm−1

T = 293 K

0.74 × 0.48 × 0.16 mm

Data collection

Stoe IPDS-2 diffractometer

Absorption correction: integration (X-RED; Stoe & Cie, 2002 ▶) T min = 0.815, T max = 0.943

10930 measured reflections

2619 independent reflections

2275 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.080

S = 1.05

2619 reflections

176 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.17 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809023447/ci2829sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809023447/ci2829Isup2.hkl

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

C13H9N3S2	F(000) = 560
Mr = 271.35	Dx = 1.461 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 17067 reflections
a = 6.2238 (3) Å	θ = 1.6–26.8°
b = 7.7393 (3) Å	µ = 0.41 mm−1
c = 25.6959 (13) Å	T = 293 K
β = 94.701 (4)°	Plate, yellow
V = 1233.55 (10) Å3	0.74 × 0.48 × 0.16 mm
Z = 4

Stoe IPDS-2 diffractometer	2619 independent reflections
Radiation source: fine-focus sealed tube	2275 reflections with I > 2σ(I)
plane graphite	Rint = 0.020
Detector resolution: 6.67 pixels mm-1	θmax = 26.8°, θmin = 1.6°
ω scans	h = −7→7
Absorption correction: integration (X-RED; Stoe & Cie, 2002)	k = −9→9
Tmin = 0.815, Tmax = 0.943	l = −32→32
10930 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.080	w = 1/[σ2(Fo2) + (0.0481P)2 + 0.1148P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
2619 reflections	Δρmax = 0.18 e Å−3
176 parameters	Δρmin = −0.17 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.002634 (11)

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
C1	0.0290 (2)	0.1603 (2)	0.57838 (6)	0.0543 (3)
C2	0.0105 (3)	0.0893 (2)	0.62710 (6)	0.0615 (4)
H2	0.1311	0.0817	0.6509	0.074*
C3	−0.1859 (3)	0.0297 (2)	0.64059 (6)	0.0621 (4)
H3	−0.1976	−0.0190	0.6733	0.075*
C4	−0.3643 (2)	0.0422 (2)	0.60563 (6)	0.0627 (4)
H4	−0.4967	0.0014	0.6147	0.075*
C5	−0.3479 (2)	0.1152 (2)	0.55709 (6)	0.0565 (3)
H5	−0.4698	0.1247	0.5338	0.068*
C6	−0.1503 (2)	0.17452 (16)	0.54281 (5)	0.0461 (3)
C7	−0.13539 (19)	0.24791 (17)	0.49053 (5)	0.0466 (3)
C8	−0.0473 (2)	0.36506 (18)	0.40911 (5)	0.0500 (3)
C9	0.2276 (2)	0.46866 (18)	0.36247 (5)	0.0500 (3)
C10	0.3030 (2)	0.55163 (17)	0.31753 (5)	0.0480 (3)
C11	0.3279 (3)	0.7018 (2)	0.23422 (6)	0.0643 (4)
H11	0.3078	0.7541	0.2016	0.077*
C12	0.5205 (3)	0.6920 (2)	0.26256 (7)	0.0631 (4)
C13	0.5080 (2)	0.60554 (18)	0.31021 (6)	0.0547 (3)
H13	0.6259	0.5869	0.3342	0.066*
N1	−0.30366 (19)	0.27346 (19)	0.45777 (5)	0.0656 (4)
N2	−0.25288 (19)	0.3405 (2)	0.41099 (5)	0.0674 (4)
N3	0.02776 (18)	0.43483 (15)	0.36467 (4)	0.0530 (3)
S1	0.10458 (5)	0.30465 (5)	0.466131 (13)	0.04910 (12)
S2	0.12673 (6)	0.60757 (5)	0.265024 (14)	0.06061 (14)
H9	0.333 (3)	0.444 (2)	0.3905 (6)	0.065 (4)*
H1	0.158 (3)	0.206 (2)	0.5694 (7)	0.071 (5)*
H12	0.645 (3)	0.736 (3)	0.2497 (8)	0.086 (6)*

	U11	U22	U33	U12	U13	U23
C1	0.0472 (7)	0.0616 (8)	0.0537 (7)	−0.0008 (6)	0.0013 (6)	−0.0007 (6)
C2	0.0579 (8)	0.0733 (10)	0.0520 (8)	0.0033 (7)	−0.0038 (6)	0.0016 (7)
C3	0.0714 (9)	0.0656 (9)	0.0502 (8)	0.0040 (7)	0.0103 (7)	0.0006 (7)
C4	0.0557 (8)	0.0725 (10)	0.0617 (9)	−0.0027 (7)	0.0151 (7)	−0.0015 (7)
C5	0.0455 (7)	0.0690 (9)	0.0549 (8)	0.0005 (6)	0.0033 (6)	−0.0047 (7)
C6	0.0460 (6)	0.0435 (7)	0.0486 (6)	0.0036 (5)	0.0032 (5)	−0.0061 (5)
C7	0.0425 (6)	0.0452 (6)	0.0516 (7)	0.0016 (5)	0.0007 (5)	−0.0035 (5)
C8	0.0466 (7)	0.0514 (7)	0.0509 (7)	0.0011 (5)	−0.0026 (5)	0.0001 (6)
C9	0.0513 (7)	0.0494 (7)	0.0483 (7)	0.0046 (6)	−0.0021 (5)	−0.0003 (6)
C10	0.0496 (7)	0.0469 (7)	0.0467 (7)	0.0051 (5)	−0.0010 (5)	−0.0019 (5)
C11	0.0729 (10)	0.0655 (9)	0.0537 (8)	−0.0013 (7)	0.0004 (7)	0.0108 (7)
C12	0.0590 (8)	0.0636 (10)	0.0670 (9)	−0.0037 (7)	0.0073 (7)	0.0085 (7)
C13	0.0503 (7)	0.0552 (8)	0.0576 (8)	0.0031 (6)	−0.0020 (6)	0.0031 (6)
N1	0.0443 (6)	0.0864 (9)	0.0647 (8)	−0.0049 (6)	−0.0039 (5)	0.0167 (7)
N2	0.0479 (6)	0.0901 (10)	0.0622 (7)	−0.0051 (6)	−0.0068 (5)	0.0208 (7)
N3	0.0518 (6)	0.0564 (7)	0.0499 (6)	−0.0003 (5)	−0.0009 (5)	0.0045 (5)
S1	0.04071 (18)	0.0581 (2)	0.04783 (19)	0.00331 (13)	−0.00016 (12)	0.00054 (14)
S2	0.0538 (2)	0.0724 (3)	0.0536 (2)	−0.00062 (16)	−0.00781 (15)	0.00514 (17)

C1—C2	1.381 (2)	C8—N3	1.3787 (18)
C1—C6	1.3875 (19)	C8—S1	1.7411 (13)
C1—H1	0.923 (18)	C9—N3	1.2770 (18)
C2—C3	1.377 (2)	C9—C10	1.4335 (19)
C2—H2	0.93	C9—H9	0.952 (16)
C3—C4	1.374 (2)	C10—C13	1.3697 (19)
C3—H3	0.93	C10—S2	1.7229 (13)
C4—C5	1.380 (2)	C11—C12	1.353 (2)
C4—H4	0.93	C11—S2	1.6993 (17)
C5—C6	1.3900 (19)	C11—H11	0.93
C5—H5	0.93	C12—C13	1.403 (2)
C6—C7	1.4684 (19)	C12—H12	0.929 (19)
C7—N1	1.3039 (17)	C13—H13	0.93
C7—S1	1.7234 (13)	N1—N2	1.3696 (19)
C8—N2	1.2987 (18)
C2—C1—C6	120.44 (14)	N2—C8—S1	113.44 (11)
C2—C1—H1	121.1 (12)	N3—C8—S1	127.22 (10)
C6—C1—H1	118.3 (11)	N3—C9—C10	120.78 (12)
C3—C2—C1	120.20 (14)	N3—C9—H9	122.7 (10)
C3—C2—H2	119.9	C10—C9—H9	116.5 (10)
C1—C2—H2	119.9	C13—C10—C9	128.09 (12)
C4—C3—C2	119.90 (14)	C13—C10—S2	110.88 (10)
C4—C3—H3	120.0	C9—C10—S2	120.94 (10)
C2—C3—H3	120.0	C12—C11—S2	112.30 (12)
C3—C4—C5	120.28 (14)	C12—C11—H11	123.9
C3—C4—H4	119.9	S2—C11—H11	123.9
C5—C4—H4	119.9	C11—C12—C13	112.73 (14)
C4—C5—C6	120.40 (14)	C11—C12—H12	121.0 (13)
C4—C5—H5	119.8	C13—C12—H12	126.3 (13)
C6—C5—H5	119.8	C10—C13—C12	112.57 (13)
C1—C6—C5	118.77 (13)	C10—C13—H13	123.7
C1—C6—C7	121.70 (12)	C12—C13—H13	123.7
C5—C6—C7	119.53 (12)	C7—N1—N2	113.15 (12)
N1—C7—C6	122.79 (12)	C8—N2—N1	112.78 (12)
N1—C7—S1	113.62 (11)	C9—N3—C8	120.94 (12)
C6—C7—S1	123.58 (9)	C7—S1—C8	87.01 (6)
N2—C8—N3	119.33 (12)	C11—S2—C10	91.51 (7)
C6—C1—C2—C3	0.9 (2)	C11—C12—C13—C10	−0.5 (2)
C1—C2—C3—C4	−0.5 (2)	C6—C7—N1—N2	−179.04 (13)
C2—C3—C4—C5	−0.3 (2)	S1—C7—N1—N2	−0.15 (18)
C3—C4—C5—C6	0.9 (2)	N3—C8—N2—N1	−178.89 (13)
C2—C1—C6—C5	−0.3 (2)	S1—C8—N2—N1	0.45 (19)
C2—C1—C6—C7	−179.40 (13)	C7—N1—N2—C8	−0.2 (2)
C4—C5—C6—C1	−0.6 (2)	C10—C9—N3—C8	−175.86 (12)
C4—C5—C6—C7	178.55 (14)	N2—C8—N3—C9	176.50 (15)
C1—C6—C7—N1	−175.17 (14)	S1—C8—N3—C9	−2.7 (2)
C5—C6—C7—N1	5.7 (2)	N1—C7—S1—C8	0.32 (12)
C1—C6—C7—S1	6.05 (19)	C6—C7—S1—C8	179.20 (12)
C5—C6—C7—S1	−173.02 (11)	N2—C8—S1—C7	−0.44 (13)
N3—C9—C10—C13	175.89 (14)	N3—C8—S1—C7	178.84 (13)
N3—C9—C10—S2	−0.24 (19)	C12—C11—S2—C10	−0.24 (14)
S2—C11—C12—C13	0.5 (2)	C13—C10—S2—C11	−0.04 (12)
C9—C10—C13—C12	−176.14 (14)	C9—C10—S2—C11	176.70 (12)
S2—C10—C13—C12	0.30 (17)