N-[(E)-Thio-phen-2-yl-methyl-idene]-1,3-benzothia-zol-2-amine.

In the title thio-phene-derived Schiff base compound, C(12)H(8)N(2)S(2), the thio-phene ring is slighty rotated from the benzothia-zole group mean plane, giving a dihedral angle of 12.87 (6)°. The largest displacement of an atom in the mol-ecule from the nine-atom mean plane defined by the non-H atoms of the benzothia-zole ring system is 0.572 (1) Å, exhibited by the C atom at the 3-position of the thio-phene ring. In the crystal, weak C-H⋯S hydrogen bonds involving the thio-phene group S atom and the 4-position thio-phene C-H group of a symmetry-related mol-ecule lead to an infinite one-dimensional chain colinear with the c axis. The structure is further stabilized by π-π inter-actions; the distance between the thia-zole ring centroid and the centroid of an adjacent benzene ring is 3.686 (1) Å. The crystal studied was an inversion twin with the ratio of components 0.73 (3):0.27 (3).

Related literature

For the synthesis and crystal structure of 2-amino­benzothia­zole, see: Ding et al. (2009 ▶). For crystal structures containing 2-amino­benzothia­zole derivatives, see: Garcia-Hernandez et al. (2006 ▶). For inhibitory properties against human cancer cell lines and general anti­tumor properties of benzothia­zole derivatives, see: Racane et al. (2001 ▶); O’Brien et al. (2003 ▶). For anti­bacterial, anti­fungal, anti­tumor and anti­viral activites of benzthia­zoles, see: Yadav & Malipatil (2011 ▶); Singh & Seghal (1988 ▶); Pattan et al. (2005 ▶).

Experimental

Crystal data

C12H8N2S2

M = 244.32

Monoclinic,

a = 10.7244 (5) Å

b = 4.6021 (2) Å

c = 11.1280 (5) Å

β = 100.367 (2)°

V = 540.25 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.46 mm−1

T = 100 K

0.45 × 0.20 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2010 ▶) T min = 0.625, T max = 0.749

14476 measured reflections

7768 independent reflections

7126 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.085

S = 1.04

7768 reflections

145 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.62 e Å−3

Δρmin = −0.36 e Å−3

Absolute structure: Flack (1983 ▶), 2974 Friedel pairs

Flack parameter: 0.27 (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: WinGX (Farrugia, 1999 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812030498/lh5495sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030498/lh5495Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812030498/lh5495Isup3.cml

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

C12H8N2S2	F(000) = 252
Mr = 244.32	Dx = 1.502 Mg m−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 7126 reflections
a = 10.7244 (5) Å	θ = 1.9–46.7°
b = 4.6021 (2) Å	µ = 0.46 mm−1
c = 11.1280 (5) Å	T = 100 K
β = 100.367 (2)°	Neelde, yellow
V = 540.25 (4) Å3	0.45 × 0.20 × 0.12 mm
Z = 2

Bruker APEXII CCD diffractometer	7768 independent reflections
Radiation source: fine-focus sealed tube	7126 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
φ and ω scans	θmax = 46.7°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2010)	h = −21→21
Tmin = 0.625, Tmax = 0.749	k = −9→9
14476 measured reflections	l = −21→22

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)] = 0.033	H-atom parameters constrained
wR(F2) = 0.085	w = 1/[σ2(Fo2) + (0.0462P)2 + 0.0113P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
7768 reflections	Δρmax = 0.62 e Å−3
145 parameters	Δρmin = −0.36 e Å−3
2 restraints	Absolute structure: Flack (1983), 2974 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.27 (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	0.784499 (18)	0.45575 (5)	0.332022 (16)	0.01350 (4)
S2	0.443816 (19)	−0.29395 (6)	0.120085 (18)	0.01726 (4)
N1	0.84951 (6)	0.36879 (17)	0.11966 (6)	0.01280 (9)
N2	0.66346 (7)	0.11200 (17)	0.15758 (6)	0.01375 (10)
C4	1.11614 (8)	0.8815 (2)	0.21064 (8)	0.01636 (12)
H4	1.1852	0.9670	0.1808	0.020*
C5	1.03822 (8)	0.68618 (19)	0.13798 (7)	0.01428 (11)
H5	1.0537	0.6364	0.0591	0.017*
C6	0.93578 (7)	0.56279 (17)	0.18281 (7)	0.01178 (10)
C7	0.76580 (7)	0.29951 (17)	0.18671 (7)	0.01226 (10)
C8	0.63195 (8)	0.02760 (18)	0.04564 (7)	0.01376 (11)
H8	0.6783	0.0935	−0.0142	0.017*
C9	0.52640 (7)	−0.16652 (18)	0.01185 (7)	0.01283 (10)
C10	0.47648 (8)	−0.2709 (2)	−0.10331 (8)	0.01632 (12)
H10	0.5091	−0.2242	−0.1749	0.020*
C11	0.37091 (9)	−0.4557 (2)	−0.10202 (9)	0.01923 (14)
H11	0.3248	−0.5476	−0.1727	0.023*
C3	1.09458 (8)	0.9554 (2)	0.32807 (9)	0.01656 (12)
H3	1.1494	1.0901	0.3761	0.020*
C2	0.99466 (8)	0.83477 (19)	0.37474 (7)	0.01491 (11)
H2	0.9803	0.8841	0.4540	0.018*
C1	0.91594 (7)	0.63843 (17)	0.30119 (7)	0.01210 (10)
C12	0.34282 (9)	−0.4870 (2)	0.01255 (10)	0.01891 (14)
H12	0.2750	−0.6026	0.0303	0.023*

	U11	U22	U33	U12	U13	U23
S1	0.01409 (7)	0.01617 (8)	0.01111 (6)	−0.00243 (6)	0.00462 (5)	−0.00251 (6)
S2	0.01686 (8)	0.02164 (9)	0.01432 (7)	−0.00281 (7)	0.00559 (6)	0.00148 (6)
N1	0.0128 (2)	0.0148 (2)	0.0111 (2)	−0.00094 (18)	0.00313 (16)	−0.00076 (18)
N2	0.0137 (2)	0.0151 (3)	0.0127 (2)	−0.00233 (19)	0.00298 (17)	−0.00149 (18)
C4	0.0137 (3)	0.0163 (3)	0.0195 (3)	−0.0015 (2)	0.0040 (2)	0.0025 (2)
C5	0.0129 (2)	0.0164 (3)	0.0143 (2)	−0.0002 (2)	0.0044 (2)	0.0016 (2)
C6	0.0117 (2)	0.0121 (3)	0.0117 (2)	0.00034 (18)	0.00274 (18)	0.00046 (18)
C7	0.0132 (2)	0.0131 (3)	0.0107 (2)	−0.0009 (2)	0.00263 (18)	−0.00112 (19)
C8	0.0142 (3)	0.0150 (3)	0.0125 (2)	−0.0025 (2)	0.0037 (2)	−0.0016 (2)
C9	0.0126 (2)	0.0142 (3)	0.0122 (2)	−0.0008 (2)	0.00370 (19)	−0.00131 (19)
C10	0.0152 (3)	0.0208 (3)	0.0138 (3)	−0.0033 (2)	0.0047 (2)	−0.0044 (2)
C11	0.0140 (3)	0.0229 (4)	0.0211 (3)	−0.0032 (3)	0.0041 (2)	−0.0073 (3)
C3	0.0140 (3)	0.0156 (3)	0.0195 (3)	−0.0028 (2)	0.0012 (2)	−0.0005 (2)
C2	0.0147 (3)	0.0147 (3)	0.0151 (3)	−0.0013 (2)	0.0020 (2)	−0.0022 (2)
C1	0.0119 (2)	0.0123 (3)	0.0122 (2)	−0.00014 (19)	0.00249 (18)	−0.00036 (19)
C12	0.0143 (3)	0.0185 (3)	0.0249 (4)	−0.0031 (2)	0.0062 (3)	−0.0015 (3)

S1—C1	1.7279 (8)	C6—C1	1.4152 (10)
S1—C7	1.7480 (7)	C8—C9	1.4379 (11)
S2—C12	1.7111 (10)	C8—H8	0.9500
S2—C9	1.7213 (8)	C9—C10	1.3830 (11)
N1—C7	1.3058 (10)	C10—C11	1.4183 (13)
N1—C6	1.3831 (10)	C10—H10	0.9500
N2—C8	1.2904 (10)	C11—C12	1.3694 (15)
N2—C7	1.3879 (10)	C11—H11	0.9500
C4—C5	1.3844 (12)	C3—C2	1.3880 (12)
C4—C3	1.4091 (13)	C3—H3	0.9500
C4—H4	0.9500	C2—C1	1.3966 (11)
C5—C6	1.4055 (11)	C2—H2	0.9500
C5—H5	0.9500	C12—H12	0.9500
C1—S1—C7	88.76 (4)	C10—C9—S2	111.59 (6)
C12—S2—C9	91.61 (4)	C8—C9—S2	120.57 (6)
C7—N1—C6	109.46 (6)	C9—C10—C11	112.06 (8)
C8—N2—C7	118.12 (7)	C9—C10—H10	124.0
C5—C4—C3	121.06 (8)	C11—C10—H10	124.0
C5—C4—H4	119.5	C12—C11—C10	112.47 (8)
C3—C4—H4	119.5	C12—C11—H11	123.8
C4—C5—C6	118.89 (7)	C10—C11—H11	123.8
C4—C5—H5	120.6	C2—C3—C4	121.13 (8)
C6—C5—H5	120.6	C2—C3—H3	119.4
N1—C6—C5	125.08 (7)	C4—C3—H3	119.4
N1—C6—C1	115.64 (7)	C3—C2—C1	117.74 (8)
C5—C6—C1	119.28 (7)	C3—C2—H2	121.1
N1—C7—N2	127.91 (7)	C1—C2—H2	121.1
N1—C7—S1	116.87 (6)	C2—C1—C6	121.90 (7)
N2—C7—S1	115.22 (6)	C2—C1—S1	128.84 (6)
N2—C8—C9	119.77 (7)	C6—C1—S1	109.26 (6)
N2—C8—H8	120.1	C11—C12—S2	112.27 (7)
C9—C8—H8	120.1	C11—C12—H12	123.9
C10—C9—C8	127.83 (7)	S2—C12—H12	123.9
C3—C4—C5—C6	0.46 (13)	C8—C9—C10—C11	−179.24 (9)
C7—N1—C6—C5	−179.28 (8)	S2—C9—C10—C11	−0.19 (11)
C7—N1—C6—C1	0.46 (10)	C9—C10—C11—C12	0.20 (13)
C4—C5—C6—N1	178.98 (8)	C5—C4—C3—C2	0.04 (14)
C4—C5—C6—C1	−0.76 (12)	C4—C3—C2—C1	−0.22 (13)
C6—N1—C7—N2	179.97 (8)	C3—C2—C1—C6	−0.10 (12)
C6—N1—C7—S1	−1.01 (9)	C3—C2—C1—S1	−179.40 (7)
C8—N2—C7—N1	−12.23 (13)	N1—C6—C1—C2	−179.17 (7)
C8—N2—C7—S1	168.73 (7)	C5—C6—C1—C2	0.60 (12)
C1—S1—C7—N1	1.00 (7)	N1—C6—C1—S1	0.26 (9)
C1—S1—C7—N2	−179.84 (6)	C5—C6—C1—S1	−179.98 (6)
C7—N2—C8—C9	−179.96 (7)	C7—S1—C1—C2	178.73 (8)
N2—C8—C9—C10	177.50 (9)	C7—S1—C1—C6	−0.64 (6)
N2—C8—C9—S2	−1.47 (12)	C10—C11—C12—S2	−0.12 (12)
C12—S2—C9—C10	0.10 (8)	C9—S2—C12—C11	0.01 (8)
C12—S2—C9—C8	179.23 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···S2i	0.95	2.92	3.517 (1)	122 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯S2i	0.95	2.92	3.517 (1)	122 (1)

Symmetry code: (i) .