N-(2-Amino-5-chloro-phen-yl)-2-bromo-benzene-sulfonamide.

In the title compound, C12H10BrClN2O2S, the sulfonamide group adopts a staggered conformation about the N-S bond [the C-S-N-H torsion angle is 97 (3)°] with the N-atom lone pair bis-ecting the O=S=O angle. For the C(Ar)-S bond, the ortho-substituted C atom bis-ects one of O=S-N angles [the C-C-S-N torsion angle is -57.7 (3)°]. The mean planes of the aromatic rings form a dihedral angle of 75.1 (1)°. In the crystal, mol-ecules form inversion dimers through pairs of N-H⋯NH2 hydrogen bonds. The mol-ecules are further consolidated into layers along the bc plane by weaker N-H⋯O inter-actions.

Related literature

For the synthesis of the title compound, see: Altamura et al. (2009 ▶). For the biological activity of sulfa drugs, see: Chegwidden et al. (2000 ▶); Lu & Tucker (2007 ▶); Tappe et al. (2008 ▶); Purushottamachar et al. (2008 ▶). For structural studies of mol­ecules having the sulfonamide –SO2—NH group, see: Parkin et al. (2008 ▶); Perlovich et al. (2009 ▶, 2011 ▶); Vega-Hissi et al. (2011 ▶); Altamura et al. (2009 ▶, 2012 ▶).

Experimental

Crystal data

C12H10BrClN2O2S

M = 361.64

Monoclinic,

a = 13.657 (1) Å

b = 14.361 (2) Å

c = 7.0829 (9) Å

β = 100.75 (1)°

V = 1364.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 3.36 mm−1

T = 298 K

0.32 × 0.26 × 0.22 mm

Data collection

Oxford Diffraction Xcalibur3 CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.365, T max = 0.447

6647 measured reflections

2533 independent reflections

1629 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.082

S = 0.94

2533 reflections

181 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.38 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PARST (Nardelli, 1995 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681204562X/ld2080sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681204562X/ld2080Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681204562X/ld2080Isup3.cml

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

C12H10BrClN2O2S	Z = 4
Mr = 361.64	F(000) = 720
Monoclinic, P21/c	Dx = 1.760 Mg m−3
a = 13.657 (1) Å	Mo Kα radiation, λ = 0.71069 Å
b = 14.361 (2) Å	µ = 3.36 mm−1
c = 7.0829 (9) Å	T = 298 K
β = 100.75 (1)°	Prismatic, colourless
V = 1364.8 (3) Å3	0.32 × 0.26 × 0.22 mm

Oxford Diffraction Xcalibur3 CCD diffractometer	2533 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1629 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 16.4547 pixels mm-1	θmax = 27.3°, θmin = 4.5°
ω scans	h = −16→16
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −17→18
Tmin = 0.365, Tmax = 0.447	l = −8→8
6647 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	w = 1/[σ2(Fo2) + (0.0371P)2] where P = (Fo2 + 2Fc2)/3
2533 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.38 e Å−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
O1	0.09409 (17)	0.35073 (16)	0.8889 (4)	0.0597 (7)
O2	0.11627 (17)	0.51070 (16)	1.0184 (3)	0.0530 (6)
S1	0.13873 (6)	0.44073 (6)	0.88946 (13)	0.0402 (2)
Cl1	0.37936 (7)	0.67877 (7)	0.45078 (14)	0.0597 (3)
Br1	0.26467 (3)	0.30924 (3)	0.61701 (6)	0.0772 (2)
C1	0.2700 (2)	0.4257 (2)	0.9480 (5)	0.0353 (8)
C2	0.3192 (3)	0.4646 (2)	1.1197 (5)	0.0501 (9)
H2	0.2842	0.5022	1.1912	0.060*
C3	0.4190 (3)	0.4482 (3)	1.1847 (6)	0.0648 (11)
H3	0.4509	0.4743	1.3000	0.078*
C4	0.4715 (3)	0.3937 (3)	1.0807 (6)	0.0626 (11)
H4	0.5389	0.3829	1.1258	0.075*
C5	0.4252 (3)	0.3548 (2)	0.9097 (6)	0.0527 (10)
H5	0.4611	0.3183	0.8380	0.063*
C6	0.3248 (2)	0.3706 (2)	0.8458 (5)	0.0419 (8)
C7	0.1417 (2)	0.5706 (2)	0.6229 (4)	0.0313 (7)
C8	0.2332 (2)	0.5803 (2)	0.5710 (4)	0.0362 (8)
H8	0.2742	0.5286	0.5697	0.043*
C9	0.2643 (2)	0.6666 (2)	0.5209 (5)	0.0373 (8)
C10	0.2038 (3)	0.7433 (2)	0.5235 (4)	0.0398 (8)
H10	0.2252	0.8016	0.4911	0.048*
C11	0.1118 (2)	0.7335 (2)	0.5742 (4)	0.0391 (8)
H11	0.0712	0.7854	0.5745	0.047*
C12	0.0789 (2)	0.6470 (2)	0.6248 (4)	0.0292 (7)
N1	0.1089 (2)	0.48048 (18)	0.6746 (4)	0.0380 (7)
HN1	0.091 (2)	0.443 (2)	0.595 (5)	0.046*
N2	−0.0166 (2)	0.6362 (2)	0.6676 (4)	0.0428 (8)
HN2A	−0.045 (3)	0.689 (2)	0.687 (5)	0.051*
HN2B	−0.021 (3)	0.597 (2)	0.750 (5)	0.051*

	U11	U22	U33	U12	U13	U23
O1	0.0480 (14)	0.0428 (15)	0.088 (2)	−0.0138 (13)	0.0117 (13)	0.0216 (13)
O2	0.0536 (15)	0.0621 (16)	0.0470 (15)	0.0154 (13)	0.0193 (12)	−0.0013 (12)
S1	0.0373 (5)	0.0376 (5)	0.0473 (5)	−0.0003 (4)	0.0122 (4)	0.0064 (4)
Cl1	0.0463 (6)	0.0695 (7)	0.0655 (7)	−0.0078 (5)	0.0160 (5)	0.0115 (5)
Br1	0.0876 (4)	0.0665 (3)	0.0700 (3)	0.0282 (2)	−0.0049 (2)	−0.0302 (2)
C1	0.0377 (19)	0.0259 (18)	0.043 (2)	−0.0002 (15)	0.0094 (16)	0.0059 (14)
C2	0.053 (2)	0.052 (2)	0.044 (2)	0.008 (2)	0.0050 (18)	−0.0004 (17)
C3	0.062 (3)	0.071 (3)	0.054 (3)	0.001 (2)	−0.009 (2)	−0.006 (2)
C4	0.042 (2)	0.065 (3)	0.077 (3)	0.006 (2)	0.003 (2)	0.012 (2)
C5	0.048 (2)	0.051 (2)	0.062 (3)	0.009 (2)	0.016 (2)	0.0096 (19)
C6	0.044 (2)	0.033 (2)	0.049 (2)	0.0027 (17)	0.0091 (17)	0.0018 (15)
C7	0.0335 (19)	0.0278 (18)	0.0318 (18)	−0.0037 (16)	0.0040 (14)	0.0002 (13)
C8	0.040 (2)	0.0309 (19)	0.038 (2)	0.0035 (16)	0.0072 (15)	0.0028 (14)
C9	0.0369 (19)	0.043 (2)	0.0308 (19)	−0.0014 (17)	0.0046 (14)	0.0013 (14)
C10	0.052 (2)	0.032 (2)	0.034 (2)	−0.0057 (18)	0.0023 (17)	0.0065 (14)
C11	0.048 (2)	0.034 (2)	0.0329 (19)	0.0083 (18)	0.0013 (16)	−0.0009 (14)
C12	0.0305 (18)	0.0313 (18)	0.0250 (17)	0.0009 (16)	0.0029 (13)	−0.0030 (13)
N1	0.0424 (17)	0.0304 (16)	0.0391 (17)	−0.0034 (14)	0.0021 (13)	−0.0018 (12)
N2	0.0429 (19)	0.040 (2)	0.046 (2)	0.0065 (16)	0.0081 (15)	−0.0001 (14)

O1—S1	1.429 (2)	C5—H5	0.9300
O2—S1	1.429 (2)	C7—C8	1.375 (4)
S1—N1	1.605 (3)	C7—C12	1.395 (4)
S1—C1	1.776 (3)	C7—N1	1.438 (4)
Cl1—C9	1.743 (3)	C8—C9	1.377 (4)
Br1—C6	1.892 (3)	C8—H8	0.9300
C1—C6	1.383 (4)	C9—C10	1.379 (4)
C1—C2	1.392 (4)	C10—C11	1.376 (4)
C2—C3	1.375 (5)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.390 (4)
C3—C4	1.366 (5)	C11—H11	0.9300
C3—H3	0.9300	C12—N2	1.402 (4)
C4—C5	1.377 (5)	N1—HN1	0.78 (3)
C4—H4	0.9300	N2—HN2A	0.87 (3)
C5—C6	1.380 (4)	N2—HN2B	0.82 (3)
O1—S1—O2	119.70 (16)	C8—C7—C12	121.0 (3)
O1—S1—N1	106.66 (16)	C8—C7—N1	120.0 (3)
O2—S1—N1	108.00 (14)	C12—C7—N1	119.0 (3)
O1—S1—C1	107.58 (14)	C7—C8—C9	119.9 (3)
O2—S1—C1	105.30 (15)	C7—C8—H8	120.0
N1—S1—C1	109.34 (15)	C9—C8—H8	120.0
C6—C1—C2	117.8 (3)	C8—C9—C10	120.1 (3)
C6—C1—S1	124.6 (3)	C8—C9—Cl1	120.1 (3)
C2—C1—S1	117.2 (3)	C10—C9—Cl1	119.8 (3)
C3—C2—C1	120.7 (3)	C11—C10—C9	120.0 (3)
C3—C2—H2	119.7	C11—C10—H10	120.0
C1—C2—H2	119.7	C9—C10—H10	120.0
C4—C3—C2	120.4 (4)	C10—C11—C12	120.9 (3)
C4—C3—H3	119.8	C10—C11—H11	119.6
C2—C3—H3	119.8	C12—C11—H11	119.6
C3—C4—C5	120.4 (4)	C11—C12—C7	118.1 (3)
C3—C4—H4	119.8	C11—C12—N2	120.9 (3)
C5—C4—H4	119.8	C7—C12—N2	120.9 (3)
C4—C5—C6	119.1 (3)	C7—N1—S1	121.7 (2)
C4—C5—H5	120.4	C7—N1—HN1	120 (3)
C6—C5—H5	120.4	S1—N1—HN1	115 (3)
C5—C6—C1	121.6 (3)	C12—N2—HN2A	114 (2)
C5—C6—Br1	116.7 (3)	C12—N2—HN2B	116 (3)
C1—C6—Br1	121.6 (2)	HN2A—N2—HN2B	112 (3)
HN1—N1—S1—C1	97 (3)	C6—C1—S1—N1	−57.7 (3)
HN1—N1—S1—O1	−19 (3)	C6—C1—S1—O1	57.8 (3)
C7—N1—S1—O2	50.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···N2i	0.78 (3)	2.26 (3)	3.022 (4)	166 (3)
N2—HN2A···O1ii	0.87 (3)	2.45 (3)	3.258 (4)	154 (3)

Table 1

Selected torsion angles (°)

HN1—N1—S1—C1	97 (3)
HN1—N1—S1—O1	−19 (3)
C7—N1—S1—O2	50.2 (3)
C6—C1—S1—N1	−57.7 (3)
C6—C1—S1—O1	57.8 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯N2i	0.78 (3)	2.26 (3)	3.022 (4)	166 (3)
N2—HN2A⋯O1ii	0.87 (3)	2.45 (3)	3.258 (4)	154 (3)

Symmetry codes: (i) ; (ii) .