7-Chloro-3-phenyl-benzo[4,5]thia-zolo[2,3-c][1,2,4]triazole.

In the title compound, C(14)H(8)ClN(3)S, the dihedral angle between the approximately planar triple-fused ring system (r.m.s. deviation = 0.065 Å) and the pendant phenyl ring is 62.25 (5)°. In the crystal, mol-ecules are linked into infinite chains along the c-axis direction by C-H⋯N hydrogen bonds. Aromatic π-π stacking inter-actions [centroid-centroid distances = 3.7499 (8) and 3.5644 (8) Å] and weak C-H⋯π inter-actions are also observed.

Related literature

For the biological activity of benzothio­zole derivatives, see: Yaseen et al. (2006 ▶); Kini et al. (2007 ▶); Munirajasekhar et al. (2011 ▶); Gurupadayya et al. (2008 ▶); Bowyer et al. (2007 ▶); Mittal et al. (2007 ▶); Pozas et al. (2005 ▶); Rana et al. (2008 ▶).

Experimental

Crystal data

C14H8ClN3S

M = 285.74

Monoclinic,

a = 16.9941 (13) Å

b = 5.8895 (5) Å

c = 12.0930 (9) Å

β = 91.770 (1)°

V = 1209.77 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.47 mm−1

T = 296 K

0.41 × 0.31 × 0.18 mm

Data collection

Bruker APEX DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.828, T max = 0.919

14981 measured reflections

4033 independent reflections

3342 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.101

S = 1.02

4033 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811039456/hb6414sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039456/hb6414Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811039456/hb6414Isup3.cml

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

C14H8ClN3S	F(000) = 584
Mr = 285.74	Dx = 1.569 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6868 reflections
a = 16.9941 (13) Å	θ = 2.4–31.4°
b = 5.8895 (5) Å	µ = 0.47 mm−1
c = 12.0930 (9) Å	T = 296 K
β = 91.770 (1)°	Block, colourless
V = 1209.77 (16) Å3	0.41 × 0.31 × 0.18 mm
Z = 4

Bruker APEX DUO CCD diffractometer	4033 independent reflections
Radiation source: fine-focus sealed tube	3342 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 31.7°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −23→25
Tmin = 0.828, Tmax = 0.919	k = −8→6
14981 measured reflections	l = −17→17

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.051P)2 + 0.2986P] where P = (Fo2 + 2Fc2)/3
4033 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.14776 (2)	0.26324 (6)	0.56813 (2)	0.04078 (10)
Cl1	0.03783 (2)	1.00056 (7)	0.32558 (4)	0.05570 (12)
N1	0.24962 (6)	0.23101 (16)	0.41312 (8)	0.03099 (19)
N2	0.31988 (7)	−0.07810 (19)	0.44194 (8)	0.0384 (2)
N3	0.26554 (7)	−0.06213 (19)	0.52726 (9)	0.0401 (2)
C1	0.35771 (8)	−0.0067 (2)	0.19026 (10)	0.0383 (3)
H1A	0.3299	−0.1423	0.1940	0.046*
C2	0.40171 (9)	0.0410 (3)	0.09818 (11)	0.0454 (3)
H2A	0.4029	−0.0621	0.0400	0.055*
C3	0.44371 (8)	0.2413 (3)	0.09278 (12)	0.0455 (3)
H3A	0.4736	0.2719	0.0314	0.055*
C4	0.44144 (8)	0.3969 (2)	0.17883 (11)	0.0430 (3)
H4A	0.4698	0.5316	0.1750	0.052*
C5	0.39691 (7)	0.3515 (2)	0.27057 (10)	0.0371 (2)
H5A	0.3948	0.4566	0.3278	0.045*
C6	0.35531 (6)	0.1482 (2)	0.27673 (9)	0.0309 (2)
C7	0.30952 (7)	0.0965 (2)	0.37544 (9)	0.0316 (2)
C8	0.22587 (7)	0.1233 (2)	0.50709 (9)	0.0344 (2)
C9	0.20460 (6)	0.42020 (19)	0.38183 (9)	0.0297 (2)
C10	0.21108 (7)	0.5535 (2)	0.28811 (9)	0.0340 (2)
H10A	0.2495	0.5239	0.2369	0.041*
C11	0.15893 (8)	0.7317 (2)	0.27264 (11)	0.0382 (3)
H11A	0.1620	0.8234	0.2103	0.046*
C12	0.10195 (7)	0.7744 (2)	0.34998 (11)	0.0383 (3)
C13	0.09432 (7)	0.6425 (2)	0.44419 (10)	0.0386 (3)
H13A	0.0559	0.6734	0.4952	0.046*
C14	0.14623 (7)	0.4629 (2)	0.45909 (9)	0.0334 (2)

	U11	U22	U33	U12	U13	U23
S1	0.04819 (18)	0.04410 (18)	0.03082 (15)	−0.00110 (13)	0.01342 (12)	0.00439 (12)
Cl1	0.0502 (2)	0.0465 (2)	0.0703 (3)	0.01117 (15)	−0.00102 (16)	0.00577 (17)
N1	0.0376 (5)	0.0308 (5)	0.0248 (4)	−0.0036 (4)	0.0054 (3)	0.0017 (3)
N2	0.0467 (5)	0.0359 (5)	0.0328 (5)	0.0011 (4)	0.0035 (4)	0.0031 (4)
N3	0.0516 (6)	0.0377 (5)	0.0313 (5)	−0.0006 (5)	0.0058 (4)	0.0061 (4)
C1	0.0435 (6)	0.0336 (6)	0.0379 (6)	−0.0007 (5)	0.0065 (5)	−0.0041 (5)
C2	0.0540 (7)	0.0473 (7)	0.0357 (6)	0.0068 (6)	0.0112 (5)	−0.0061 (5)
C3	0.0442 (7)	0.0528 (8)	0.0403 (6)	0.0066 (6)	0.0146 (5)	0.0078 (6)
C4	0.0399 (6)	0.0421 (7)	0.0475 (7)	−0.0046 (5)	0.0072 (5)	0.0075 (5)
C5	0.0394 (6)	0.0360 (6)	0.0362 (6)	−0.0041 (5)	0.0037 (4)	−0.0035 (5)
C6	0.0319 (5)	0.0317 (5)	0.0292 (5)	0.0004 (4)	0.0026 (4)	0.0001 (4)
C7	0.0361 (5)	0.0306 (5)	0.0283 (5)	−0.0018 (4)	0.0027 (4)	−0.0017 (4)
C8	0.0436 (6)	0.0353 (6)	0.0246 (5)	−0.0056 (5)	0.0054 (4)	0.0032 (4)
C9	0.0342 (5)	0.0289 (5)	0.0261 (4)	−0.0042 (4)	0.0022 (4)	−0.0007 (4)
C10	0.0384 (5)	0.0351 (6)	0.0288 (5)	−0.0050 (4)	0.0040 (4)	0.0021 (4)
C11	0.0412 (6)	0.0370 (6)	0.0361 (6)	−0.0036 (5)	−0.0017 (4)	0.0066 (5)
C12	0.0364 (5)	0.0334 (6)	0.0449 (6)	−0.0014 (4)	−0.0027 (5)	0.0004 (5)
C13	0.0367 (6)	0.0395 (6)	0.0398 (6)	−0.0018 (5)	0.0061 (4)	−0.0038 (5)
C14	0.0373 (5)	0.0343 (5)	0.0288 (5)	−0.0049 (4)	0.0054 (4)	−0.0003 (4)

S1—C8	1.7454 (13)	C3—H3A	0.9300
S1—C14	1.7663 (12)	C4—C5	1.3881 (17)
Cl1—C12	1.7405 (13)	C4—H4A	0.9300
N1—C8	1.3729 (13)	C5—C6	1.3935 (16)
N1—C7	1.3783 (15)	C5—H5A	0.9300
N1—C9	1.3972 (14)	C6—C7	1.4768 (15)
N2—C7	1.3140 (16)	C9—C10	1.3860 (15)
N2—N3	1.4088 (15)	C9—C14	1.4062 (15)
N3—C8	1.3026 (17)	C10—C11	1.3826 (17)
C1—C6	1.3895 (16)	C10—H10A	0.9300
C1—C2	1.3891 (18)	C11—C12	1.3898 (19)
C1—H1A	0.9300	C11—H11A	0.9300
C2—C3	1.381 (2)	C12—C13	1.3882 (18)
C2—H2A	0.9300	C13—C14	1.3856 (17)
C3—C4	1.388 (2)	C13—H13A	0.9300
C8—S1—C14	89.57 (5)	N2—C7—N1	109.50 (10)
C8—N1—C7	104.31 (10)	N2—C7—C6	126.31 (11)
C8—N1—C9	114.84 (10)	N1—C7—C6	124.17 (10)
C7—N1—C9	140.59 (9)	N3—C8—N1	112.25 (10)
C7—N2—N3	108.51 (10)	N3—C8—S1	135.45 (9)
C8—N3—N2	105.43 (10)	N1—C8—S1	112.26 (9)
C6—C1—C2	119.94 (12)	C10—C9—N1	128.07 (10)
C6—C1—H1A	120.0	C10—C9—C14	121.17 (11)
C2—C1—H1A	120.0	N1—C9—C14	110.75 (10)
C3—C2—C1	120.18 (13)	C11—C10—C9	118.29 (11)
C3—C2—H2A	119.9	C11—C10—H10A	120.9
C1—C2—H2A	119.9	C9—C10—H10A	120.9
C2—C3—C4	120.13 (12)	C10—C11—C12	120.20 (12)
C2—C3—H3A	119.9	C10—C11—H11A	119.9
C4—C3—H3A	119.9	C12—C11—H11A	119.9
C3—C4—C5	120.03 (13)	C11—C12—C13	122.41 (12)
C3—C4—H4A	120.0	C11—C12—Cl1	118.02 (10)
C5—C4—H4A	120.0	C13—C12—Cl1	119.57 (10)
C4—C5—C6	119.88 (12)	C14—C13—C12	117.30 (11)
C4—C5—H5A	120.1	C14—C13—H13A	121.3
C6—C5—H5A	120.1	C12—C13—H13A	121.3
C1—C6—C5	119.83 (10)	C13—C14—C9	120.62 (11)
C1—C6—C7	120.08 (11)	C13—C14—S1	126.87 (9)
C5—C6—C7	120.09 (10)	C9—C14—S1	112.50 (9)
C7—N2—N3—C8	−0.41 (14)	C7—N1—C8—S1	−178.75 (8)
C6—C1—C2—C3	0.6 (2)	C9—N1—C8—S1	−3.47 (13)
C1—C2—C3—C4	−0.7 (2)	C14—S1—C8—N3	−175.12 (14)
C2—C3—C4—C5	0.0 (2)	C14—S1—C8—N1	2.37 (9)
C3—C4—C5—C6	0.8 (2)	C8—N1—C9—C10	−175.66 (11)
C2—C1—C6—C5	0.19 (19)	C7—N1—C9—C10	−2.9 (2)
C2—C1—C6—C7	−179.13 (12)	C8—N1—C9—C14	2.82 (14)
C4—C5—C6—C1	−0.91 (18)	C7—N1—C9—C14	175.61 (13)
C4—C5—C6—C7	178.41 (11)	N1—C9—C10—C11	178.84 (11)
N3—N2—C7—N1	0.01 (13)	C14—C9—C10—C11	0.51 (17)
N3—N2—C7—C6	178.56 (11)	C9—C10—C11—C12	0.20 (18)
C8—N1—C7—N2	0.37 (13)	C10—C11—C12—C13	−0.4 (2)
C9—N1—C7—N2	−172.89 (13)	C10—C11—C12—Cl1	−179.79 (9)
C8—N1—C7—C6	−178.22 (10)	C11—C12—C13—C14	−0.12 (19)
C9—N1—C7—C6	8.5 (2)	Cl1—C12—C13—C14	179.26 (9)
C1—C6—C7—N2	59.23 (17)	C12—C13—C14—C9	0.83 (17)
C5—C6—C7—N2	−120.09 (14)	C12—C13—C14—S1	−177.69 (9)
C1—C6—C7—N1	−122.43 (13)	C10—C9—C14—C13	−1.05 (17)
C5—C6—C7—N1	58.25 (16)	N1—C9—C14—C13	−179.65 (10)
N2—N3—C8—N1	0.66 (14)	C10—C9—C14—S1	177.67 (9)
N2—N3—C8—S1	178.15 (11)	N1—C9—C14—S1	−0.93 (12)
C7—N1—C8—N3	−0.66 (13)	C8—S1—C14—C13	177.83 (12)
C9—N1—C8—N3	174.63 (10)	C8—S1—C14—C9	−0.79 (9)

Cg3 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···N3i	0.93	2.57	3.3135 (16)	138
C4—H4A···Cg3ii	0.93	2.92	3.5851 (15)	130

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯N3i	0.93	2.57	3.3135 (16)	138
C4—H4A⋯Cg3ii	0.93	2.92	3.5851 (15)	130

Symmetry codes: (i) ; (ii) .