2-(2-Nitro-phen-yl)-1,3-benzothia-zole.

In the title compound, C(13)H(8)N(2)O(2)S, the essentially planar benzothia-zole system [maximum deviation = -0.012 (1) Å for the S atom] is oriented at a dihedral angle of 48.3 (1)° with respect to the benzene ring. The nitro group is substanti-ally twisted from the plane of its attached benzene ring [dihedral angle = 52.0 (1)°]. The crystal packing features C-H⋯O hydrogen bonds, which generate C(6) helical chains propagating along [010]. Weak C-H⋯π inter-actions also occur in the crystal.

Related literature

For the pharmacological activity of benzothia­zole derivatives, see: Repiĉ et al. (2001 ▶); Schwartz et al. (1992 ▶). For related structures, see: Lakshmanan et al. (2011 ▶); Zhang et al. (2008 ▶).

Experimental

Crystal data

C13H8N2O2S

M = 256.27

Monoclinic,

a = 7.6092 (2) Å

b = 12.7854 (3) Å

c = 11.9938 (3) Å

β = 90.556 (2)°

V = 1166.78 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 293 K

0.24 × 0.22 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.937, T max = 0.958

14037 measured reflections

3258 independent reflections

2559 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.113

S = 1.05

3258 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia (1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812029844/hb6879sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029844/hb6879Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812029844/hb6879Isup3.cml

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

C13H8N2O2S	F(000) = 528
Mr = 256.27	Dx = 1.459 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3261 reflections
a = 7.6092 (2) Å	θ = 2.3–29.5°
b = 12.7854 (3) Å	µ = 0.27 mm−1
c = 11.9938 (3) Å	T = 293 K
β = 90.556 (2)°	Block, yellow
V = 1166.78 (5) Å3	0.24 × 0.22 × 0.16 mm
Z = 4

Bruker APEXII CCD diffractometer	3258 independent reflections
Radiation source: fine-focus sealed tube	2559 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 10.0 pixels mm-1	θmax = 29.5°, θmin = 2.3°
ω scans	h = −6→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −17→17
Tmin = 0.937, Tmax = 0.958	l = −16→16
14037 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0565P)2 + 0.2357P] where P = (Fo2 + 2Fc2)/3
3258 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.32 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
C1	0.23422 (17)	0.05259 (10)	0.59828 (11)	0.0353 (3)
C2	0.16130 (18)	0.21138 (10)	0.64971 (11)	0.0363 (3)
C3	0.0966 (2)	0.29175 (12)	0.71628 (13)	0.0480 (3)
H3	0.0530	0.2776	0.7869	0.058*
C4	0.0984 (2)	0.39208 (12)	0.67587 (16)	0.0548 (4)
H4	0.0561	0.4462	0.7199	0.066*
C5	0.1620 (2)	0.41411 (12)	0.57096 (16)	0.0560 (4)
H5	0.1621	0.4830	0.5460	0.067*
C6	0.2249 (2)	0.33699 (12)	0.50273 (15)	0.0531 (4)
H6	0.2667	0.3523	0.4320	0.064*
C7	0.22399 (19)	0.23476 (11)	0.54327 (12)	0.0404 (3)
C8	0.26409 (17)	−0.06135 (10)	0.60273 (11)	0.0362 (3)
C9	0.2087 (2)	−0.12556 (11)	0.51565 (13)	0.0465 (3)
H9	0.1533	−0.0963	0.4536	0.056*
C10	0.2349 (2)	−0.23238 (12)	0.52027 (15)	0.0542 (4)
H10	0.1979	−0.2743	0.4612	0.065*
C11	0.3152 (2)	−0.27701 (11)	0.61136 (16)	0.0546 (4)
H11	0.3325	−0.3490	0.6137	0.065*
C12	0.3705 (2)	−0.21558 (11)	0.69957 (14)	0.0470 (3)
H12	0.4235	−0.2455	0.7621	0.056*
C13	0.34560 (18)	−0.10908 (10)	0.69301 (11)	0.0376 (3)
N1	0.16909 (16)	0.10658 (8)	0.67886 (9)	0.0385 (3)
N2	0.42054 (19)	−0.04475 (10)	0.78230 (11)	0.0482 (3)
O1	0.51720 (18)	0.02623 (10)	0.75526 (12)	0.0675 (4)
O2	0.3857 (2)	−0.06687 (13)	0.87769 (10)	0.0812 (4)
S1	0.29145 (6)	0.12103 (3)	0.47927 (3)	0.04852 (13)

	U11	U22	U33	U12	U13	U23
C1	0.0351 (6)	0.0335 (6)	0.0372 (6)	0.0036 (5)	−0.0008 (5)	0.0019 (5)
C2	0.0360 (7)	0.0340 (6)	0.0389 (6)	0.0019 (5)	−0.0033 (5)	−0.0014 (5)
C3	0.0543 (9)	0.0430 (7)	0.0469 (8)	0.0053 (6)	0.0005 (7)	−0.0092 (6)
C4	0.0577 (10)	0.0379 (7)	0.0687 (10)	0.0062 (7)	−0.0064 (8)	−0.0153 (7)
C5	0.0586 (10)	0.0316 (7)	0.0776 (11)	−0.0010 (7)	−0.0063 (8)	0.0036 (7)
C6	0.0607 (10)	0.0383 (8)	0.0605 (9)	−0.0017 (7)	0.0062 (8)	0.0109 (7)
C7	0.0416 (7)	0.0338 (6)	0.0459 (7)	0.0012 (5)	0.0020 (6)	0.0019 (5)
C8	0.0339 (6)	0.0326 (6)	0.0422 (7)	0.0034 (5)	−0.0006 (5)	−0.0012 (5)
C9	0.0464 (8)	0.0423 (7)	0.0506 (8)	0.0074 (6)	−0.0117 (7)	−0.0064 (6)
C10	0.0537 (9)	0.0404 (8)	0.0681 (11)	0.0038 (7)	−0.0123 (8)	−0.0167 (7)
C11	0.0561 (9)	0.0309 (7)	0.0766 (11)	0.0033 (6)	−0.0052 (8)	−0.0038 (7)
C12	0.0489 (8)	0.0362 (7)	0.0559 (8)	0.0048 (6)	−0.0032 (7)	0.0064 (6)
C13	0.0373 (7)	0.0336 (6)	0.0417 (7)	0.0013 (5)	−0.0006 (5)	−0.0005 (5)
N1	0.0442 (6)	0.0345 (5)	0.0368 (5)	0.0048 (4)	0.0009 (5)	0.0007 (4)
N2	0.0552 (8)	0.0416 (6)	0.0476 (7)	0.0074 (6)	−0.0130 (6)	−0.0025 (5)
O1	0.0702 (8)	0.0496 (7)	0.0822 (9)	−0.0119 (6)	−0.0263 (7)	−0.0049 (6)
O2	0.1183 (13)	0.0836 (10)	0.0414 (6)	0.0026 (9)	−0.0075 (7)	−0.0013 (6)
S1	0.0620 (3)	0.0411 (2)	0.0428 (2)	0.00900 (16)	0.01624 (17)	0.00421 (14)

C1—N1	1.2906 (17)	C7—S1	1.7247 (14)
C1—C8	1.4752 (18)	C8—C13	1.3844 (19)
C1—S1	1.7335 (13)	C8—C9	1.391 (2)
C2—N1	1.3858 (17)	C9—C10	1.381 (2)
C2—C3	1.3940 (19)	C9—H9	0.9300
C2—C7	1.400 (2)	C10—C11	1.371 (2)
C3—C4	1.371 (2)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.380 (2)
C4—C5	1.381 (3)	C11—H11	0.9300
C4—H4	0.9300	C12—C13	1.3770 (18)
C5—C6	1.371 (3)	C12—H12	0.9300
C5—H5	0.9300	C13—N2	1.4617 (18)
C6—C7	1.395 (2)	N2—O2	1.2103 (18)
C6—H6	0.9300	N2—O1	1.2142 (19)
N1—C1—C8	124.15 (12)	C13—C8—C1	122.09 (12)
N1—C1—S1	116.61 (10)	C9—C8—C1	120.68 (12)
C8—C1—S1	119.24 (10)	C10—C9—C8	120.72 (14)
N1—C2—C3	125.64 (13)	C10—C9—H9	119.6
N1—C2—C7	115.00 (11)	C8—C9—H9	119.6
C3—C2—C7	119.36 (13)	C11—C10—C9	120.44 (15)
C4—C3—C2	118.84 (15)	C11—C10—H10	119.8
C4—C3—H3	120.6	C9—C10—H10	119.8
C2—C3—H3	120.6	C10—C11—C12	120.29 (14)
C3—C4—C5	121.16 (15)	C10—C11—H11	119.9
C3—C4—H4	119.4	C12—C11—H11	119.9
C5—C4—H4	119.4	C13—C12—C11	118.56 (14)
C6—C5—C4	121.63 (15)	C13—C12—H12	120.7
C6—C5—H5	119.2	C11—C12—H12	120.7
C4—C5—H5	119.2	C12—C13—C8	122.75 (13)
C5—C6—C7	117.59 (16)	C12—C13—N2	117.52 (13)
C5—C6—H6	121.2	C8—C13—N2	119.58 (11)
C7—C6—H6	121.2	C1—N1—C2	110.13 (11)
C6—C7—C2	121.41 (14)	O2—N2—O1	124.46 (15)
C6—C7—S1	129.23 (12)	O2—N2—C13	118.28 (14)
C2—C7—S1	109.36 (10)	O1—N2—C13	117.25 (13)
C13—C8—C9	117.22 (12)	C7—S1—C1	88.91 (6)
N1—C2—C3—C4	179.67 (15)	C10—C11—C12—C13	−1.0 (3)
C7—C2—C3—C4	−0.8 (2)	C11—C12—C13—C8	1.4 (2)
C2—C3—C4—C5	0.3 (3)	C11—C12—C13—N2	−174.13 (15)
C3—C4—C5—C6	0.4 (3)	C9—C8—C13—C12	−0.9 (2)
C4—C5—C6—C7	−0.5 (3)	C1—C8—C13—C12	178.36 (14)
C5—C6—C7—C2	0.0 (2)	C9—C8—C13—N2	174.55 (14)
C5—C6—C7—S1	179.49 (13)	C1—C8—C13—N2	−6.2 (2)
N1—C2—C7—C6	−179.77 (14)	C8—C1—N1—C2	178.70 (12)
C3—C2—C7—C6	0.7 (2)	S1—C1—N1—C2	−0.41 (15)
N1—C2—C7—S1	0.64 (16)	C3—C2—N1—C1	179.35 (14)
C3—C2—C7—S1	−178.90 (11)	C7—C2—N1—C1	−0.16 (17)
N1—C1—C8—C13	−47.3 (2)	C12—C13—N2—O2	−52.8 (2)
S1—C1—C8—C13	131.81 (12)	C8—C13—N2—O2	131.55 (16)
N1—C1—C8—C9	131.96 (15)	C12—C13—N2—O1	125.64 (16)
S1—C1—C8—C9	−48.95 (18)	C8—C13—N2—O1	−50.05 (19)
C13—C8—C9—C10	0.0 (2)	C6—C7—S1—C1	179.76 (16)
C1—C8—C9—C10	−179.32 (14)	C2—C7—S1—C1	−0.69 (11)
C8—C9—C10—C11	0.4 (3)	N1—C1—S1—C7	0.67 (12)
C9—C10—C11—C12	0.1 (3)	C8—C1—S1—C7	−178.49 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1i	0.93	2.51	3.236 (2)	135
C9—H9···Cg1ii	0.93	2.92	3.468 (2)	119
C10—H10···Cg2ii	0.93	2.90	3.536 (2)	127
C3—H3···Cg3iii	0.93	2.99	3.673 (2)	132

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the S1/N1/C1/C2/C7 thiazole ring, the C2–C7 benzene ring and the C8–C13 benzene ring, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O1i	0.93	2.51	3.236 (2)	135
C9—H9⋯Cg1ii	0.93	2.92	3.468 (2)	119
C10—H10⋯Cg2ii	0.93	2.90	3.536 (2)	127
C3—H3⋯Cg3iii	0.93	2.99	3.673 (2)	132

Symmetry codes: (i) ; (ii) ; (iii) .