2-[(3-Bromo-anilino)meth-yl]-1,2-benzo-thia-zol-3(2H)-one.

The title compound, C(14)H(11)BrN(2)OS, was synthesized by the reaction of 1,2-benzothia-zol-3(2H)-one with formalin and 3-bromo-aniline in ethanol. The 1,2-benzothia-zolone ring system is approximately planar [maximum deviation = 0.0142 (s.u.?) Å] and forms a dihedral angle of 79.19 (5)° with the benzene ring. In the crystal, molecules are linked by N-H⋯O, C-H⋯O and C-H⋯Br interactions.

Related literature

For background to the synthesis of benzoisothia­zolone deriv­atives, see: Davis (1972 ▶); Elgazwy & Abdel-Sattar (2003 ▶). For the biological activity of 1,2-benzoisothia­zolone derivatives, see: Taubert et al. (2002 ▶). For structural studies of related alkyl 3-oxo-2,3-dihydro-1,2-benzothia­zole-2-carboxyl­ate derivatives, see: Wang et al. (2011 ▶); Wang, Yang et al. (2011a ▶,b ▶)

Experimental

Crystal data

C14H11BrN2OS

M = 335.22

Monoclinic,

a = 7.351 (2) Å

b = 22.781 (7) Å

c = 8.559 (3) Å

β = 109.580 (4)°

V = 1350.5 (7) Å3

Z = 4

Mo Kα radiation

μ = 3.19 mm−1

T = 153 K

0.38 × 0.37 × 0.31 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.374, T max = 0.436

11631 measured reflections

3587 independent reflections

2709 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.069

S = 1.00

3587 reflections

176 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.52 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812012263/rz2723sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012263/rz2723Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812012263/rz2723Isup3.cml

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

C14H11BrN2OS	F(000) = 672
Mr = 335.22	Dx = 1.649 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4184 reflections
a = 7.351 (2) Å	θ = 2.7–29.1°
b = 22.781 (7) Å	µ = 3.19 mm−1
c = 8.559 (3) Å	T = 153 K
β = 109.580 (4)°	Block, colourless
V = 1350.5 (7) Å3	0.38 × 0.37 × 0.31 mm
Z = 4

Rigaku AFC10/Saturn724+ diffractometer	3587 independent reflections
Radiation source: Rotating Anode	2709 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
Detector resolution: 28.5714 pixels mm-1	θmax = 29.1°, θmin = 2.7°
phi and ω scans	h = −10→9
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −31→30
Tmin = 0.374, Tmax = 0.436	l = −11→11
11631 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0289P)2 + 0.160P] where P = (Fo2 + 2Fc2)/3
3587 reflections	(Δ/σ)max < 0.001
176 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.52 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
Br1	0.37553 (3)	0.693276 (11)	0.83530 (3)	0.03101 (8)
O1	1.1959 (2)	0.47887 (6)	1.16801 (16)	0.0223 (3)
S1	1.30876 (8)	0.60263 (2)	1.48237 (6)	0.02068 (12)
N1	1.2660 (2)	0.56804 (7)	1.29651 (19)	0.0181 (4)
C13	0.6410 (3)	0.69583 (9)	0.9710 (3)	0.0220 (4)
C7	1.2302 (3)	0.50892 (9)	1.2939 (2)	0.0174 (4)
N2	1.0771 (2)	0.60956 (8)	1.0275 (2)	0.0184 (4)
C5	1.2107 (3)	0.43397 (10)	1.5099 (3)	0.0218 (4)
H5	1.1821	0.4025	1.4327	0.026*
C3	1.2648 (3)	0.47107 (10)	1.7852 (3)	0.0253 (5)
H3	1.2716	0.4638	1.8963	0.030*
C1	1.2822 (3)	0.53648 (9)	1.5741 (2)	0.0181 (4)
C9	0.9559 (3)	0.65290 (9)	1.0506 (2)	0.0172 (4)
C10	1.0203 (3)	0.69745 (9)	1.1676 (3)	0.0261 (5)
H10	1.1519	0.6985	1.2368	0.031*
C14	0.7614 (3)	0.65249 (9)	0.9498 (2)	0.0182 (4)
H14	0.7134	0.6229	0.8682	0.022*
C6	1.2401 (3)	0.49047 (9)	1.4604 (2)	0.0168 (4)
C8	1.2648 (3)	0.59860 (9)	1.1440 (2)	0.0184 (4)
H8A	1.3328	0.6366	1.1755	0.022*
H8B	1.3384	0.5747	1.0891	0.022*
C2	1.2955 (3)	0.52715 (10)	1.7396 (3)	0.0237 (5)
H2	1.3246	0.5584	1.8174	0.028*
C4	1.2239 (3)	0.42447 (10)	1.6723 (3)	0.0259 (5)
H4	1.2051	0.3861	1.7078	0.031*
C12	0.7015 (3)	0.74034 (11)	1.0860 (3)	0.0324 (5)
H12	0.6149	0.7697	1.0973	0.039*
C11	0.8935 (4)	0.74030 (11)	1.1840 (3)	0.0349 (6)
H11	0.9402	0.7703	1.2645	0.042*
H2N	1.017 (3)	0.5816 (10)	0.975 (3)	0.023 (6)*

	U11	U22	U33	U12	U13	U23
Br1	0.02204 (12)	0.03134 (14)	0.03771 (15)	0.00613 (10)	0.00744 (9)	0.00158 (11)
O1	0.0263 (8)	0.0235 (8)	0.0165 (8)	−0.0016 (7)	0.0064 (6)	−0.0054 (6)
S1	0.0272 (3)	0.0200 (3)	0.0155 (3)	−0.0026 (2)	0.0080 (2)	−0.0035 (2)
N1	0.0253 (9)	0.0177 (9)	0.0124 (9)	−0.0007 (7)	0.0076 (7)	−0.0009 (7)
C13	0.0227 (10)	0.0203 (11)	0.0235 (12)	0.0014 (9)	0.0083 (9)	0.0035 (9)
C7	0.0150 (9)	0.0194 (11)	0.0166 (11)	0.0010 (8)	0.0038 (8)	−0.0013 (8)
N2	0.0189 (9)	0.0179 (9)	0.0162 (9)	0.0000 (7)	0.0029 (7)	−0.0024 (7)
C5	0.0182 (10)	0.0234 (11)	0.0229 (12)	0.0000 (9)	0.0059 (8)	0.0005 (9)
C3	0.0220 (11)	0.0365 (13)	0.0191 (12)	0.0016 (10)	0.0092 (9)	0.0068 (10)
C1	0.0137 (9)	0.0231 (11)	0.0178 (11)	−0.0009 (8)	0.0054 (8)	0.0001 (8)
C9	0.0207 (10)	0.0151 (10)	0.0164 (10)	0.0000 (8)	0.0071 (8)	0.0024 (8)
C10	0.0239 (11)	0.0211 (11)	0.0289 (13)	−0.0026 (10)	0.0032 (9)	−0.0066 (9)
C14	0.0228 (11)	0.0176 (10)	0.0150 (11)	−0.0001 (8)	0.0073 (8)	0.0006 (8)
C6	0.0128 (9)	0.0212 (10)	0.0155 (10)	0.0019 (8)	0.0038 (7)	0.0014 (8)
C8	0.0208 (10)	0.0215 (11)	0.0154 (10)	−0.0010 (9)	0.0095 (8)	0.0005 (8)
C2	0.0229 (11)	0.0314 (13)	0.0177 (11)	0.0002 (9)	0.0079 (9)	−0.0016 (9)
C4	0.0232 (11)	0.0277 (12)	0.0279 (13)	0.0004 (10)	0.0098 (9)	0.0081 (10)
C12	0.0337 (13)	0.0256 (12)	0.0389 (14)	0.0061 (11)	0.0134 (11)	−0.0091 (11)
C11	0.0392 (14)	0.0251 (13)	0.0382 (14)	−0.0003 (11)	0.0100 (11)	−0.0165 (11)

Br1—C13	1.908 (2)	C3—C4	1.398 (3)
O1—C7	1.229 (2)	C3—H3	0.9500
S1—N1	1.7074 (17)	C1—C6	1.393 (3)
S1—C1	1.740 (2)	C1—C2	1.403 (3)
N1—C7	1.371 (3)	C9—C10	1.393 (3)
N1—C8	1.476 (2)	C9—C14	1.401 (3)
C13—C14	1.378 (3)	C10—C11	1.389 (3)
C13—C12	1.379 (3)	C10—H10	0.9500
C7—C6	1.464 (3)	C14—H14	0.9500
N2—C9	1.388 (3)	C8—H8A	0.9900
N2—C8	1.427 (2)	C8—H8B	0.9900
N2—H2N	0.82 (2)	C2—H2	0.9500
C5—C4	1.378 (3)	C4—H4	0.9500
C5—C6	1.394 (3)	C12—C11	1.379 (3)
C5—H5	0.9500	C12—H12	0.9500
C3—C2	1.376 (3)	C11—H11	0.9500
N1—S1—C1	90.41 (9)	C11—C10—H10	119.8
C7—N1—C8	120.30 (16)	C9—C10—H10	119.8
C7—N1—S1	116.28 (13)	C13—C14—C9	118.83 (19)
C8—N1—S1	123.42 (13)	C13—C14—H14	120.6
C14—C13—C12	123.6 (2)	C9—C14—H14	120.6
C14—C13—Br1	117.97 (16)	C1—C6—C5	120.22 (18)
C12—C13—Br1	118.46 (17)	C1—C6—C7	113.01 (18)
O1—C7—N1	122.90 (18)	C5—C6—C7	126.76 (18)
O1—C7—C6	128.46 (19)	N2—C8—N1	114.72 (16)
N1—C7—C6	108.64 (17)	N2—C8—H8A	108.6
C9—N2—C8	122.78 (18)	N1—C8—H8A	108.6
C9—N2—H2N	112.0 (16)	N2—C8—H8B	108.6
C8—N2—H2N	117.8 (16)	N1—C8—H8B	108.6
C4—C5—C6	119.1 (2)	H8A—C8—H8B	107.6
C4—C5—H5	120.5	C3—C2—C1	117.7 (2)
C6—C5—H5	120.5	C3—C2—H2	121.2
C2—C3—C4	121.8 (2)	C1—C2—H2	121.2
C2—C3—H3	119.1	C5—C4—C3	120.3 (2)
C4—C3—H3	119.1	C5—C4—H4	119.9
C6—C1—C2	121.0 (2)	C3—C4—H4	119.9
C6—C1—S1	111.65 (15)	C13—C12—C11	116.9 (2)
C2—C1—S1	127.33 (17)	C13—C12—H12	121.5
N2—C9—C10	122.76 (19)	C11—C12—H12	121.5
N2—C9—C14	118.63 (19)	C12—C11—C10	121.6 (2)
C10—C9—C14	118.60 (19)	C12—C11—H11	119.2
C11—C10—C9	120.5 (2)	C10—C11—H11	119.2
C1—S1—N1—C7	0.55 (16)	S1—C1—C6—C7	0.5 (2)
C1—S1—N1—C8	−179.97 (16)	C4—C5—C6—C1	0.1 (3)
C8—N1—C7—O1	0.0 (3)	C4—C5—C6—C7	−179.39 (19)
S1—N1—C7—O1	179.45 (15)	O1—C7—C6—C1	−179.89 (19)
C8—N1—C7—C6	−179.87 (16)	N1—C7—C6—C1	−0.1 (2)
S1—N1—C7—C6	−0.4 (2)	O1—C7—C6—C5	−0.4 (3)
N1—S1—C1—C6	−0.57 (15)	N1—C7—C6—C5	179.41 (18)
N1—S1—C1—C2	−179.34 (19)	C9—N2—C8—N1	74.6 (2)
C8—N2—C9—C10	14.7 (3)	C7—N1—C8—N2	76.3 (2)
C8—N2—C9—C14	−166.54 (18)	S1—N1—C8—N2	−103.16 (19)
N2—C9—C10—C11	179.0 (2)	C4—C3—C2—C1	0.7 (3)
C14—C9—C10—C11	0.3 (3)	C6—C1—C2—C3	−0.2 (3)
C12—C13—C14—C9	0.5 (3)	S1—C1—C2—C3	178.47 (16)
Br1—C13—C14—C9	−178.70 (15)	C6—C5—C4—C3	0.4 (3)
N2—C9—C14—C13	−179.28 (18)	C2—C3—C4—C5	−0.9 (3)
C10—C9—C14—C13	−0.5 (3)	C14—C13—C12—C11	−0.3 (4)
C2—C1—C6—C5	−0.2 (3)	Br1—C13—C12—C11	178.94 (18)
S1—C1—C6—C5	−179.05 (15)	C13—C12—C11—C10	0.0 (4)
C2—C1—C6—C7	179.34 (18)	C9—C10—C11—C12	0.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1i	0.82 (2)	2.14 (2)	2.939 (2)	167 (2)
C3—H3···O1ii	0.95	2.59	3.484 (3)	157
C10—H10···Br1iii	0.95	2.93	3.545 (3)	124
C14—H14···O1i	0.95	2.46	3.207 (3)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O1i	0.82 (2)	2.14 (2)	2.939 (2)	167 (2)
C3—H3⋯O1ii	0.95	2.59	3.484 (3)	157
C10—H10⋯Br1iii	0.95	2.93	3.545 (3)	124
C14—H14⋯O1i	0.95	2.46	3.207 (3)	135

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