Methyl 2-bromo-3-(4-chloro-benzene-sulfonamido)-benzoate.

In the crystal structure of the title compound, C(14)H(11)BrClNO(4)S, the mol-ecules form inversion dimers with R(2) (2)(8) motifs through pairs of N-H⋯O hydrogen bonds. The benzene rings are not coplanar and subtend a dihedral angle of 66.27 (8)°. The carbomethoxy group makes a dihedral angle of 75.1 (1)° with the ring to which it is attached.

Related literature

Depending on their substitution patterns, sulfonamides display a wide array of biological activity. For their use as anti­mitotic, anti­bacterial and anti-obesity agents, see: Hu et al. (2008 ▶); Wydysh et al. (2009 ▶). For structures related to the development of novel anti­microbial agents, see: Kulkarni et al. (2012a ▶,b ▶).

Experimental

Crystal data

C14H11BrClNO4S

M = 404.66

Monoclinic,

a = 7.9206 (2) Å

b = 9.4600 (3) Å

c = 20.0915 (6) Å

β = 94.505 (3)°

V = 1500.79 (8) Å3

Z = 4

Cu Kα radiation

μ = 6.84 mm−1

T = 123 K

1.06 × 0.88 × 0.52 mm

Data collection

Agilent Xcalibur (Ruby, Gemini) diffractometer

Absorption correction: analytical [CrysAlis PRO (Agilent, 2010 ▶), based on expressions derived by Clark & Reid (1995 ▶)] T min = 0.049, T max = 0.198

5248 measured reflections

3012 independent reflections

2873 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.093

S = 1.08

3012 reflections

205 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.48 e Å−3

Δρmin = −0.65 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812048581/ds2221sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812048581/ds2221Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812048581/ds2221Isup3.cml

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

C14H11BrClNO4S	F(000) = 808
Mr = 404.66	Dx = 1.791 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 3046 reflections
a = 7.9206 (2) Å	θ = 4.4–75.7°
b = 9.4600 (3) Å	µ = 6.84 mm−1
c = 20.0915 (6) Å	T = 123 K
β = 94.505 (3)°	Chunk, colorless
V = 1500.79 (8) Å3	1.06 × 0.88 × 0.52 mm
Z = 4

Agilent Xcalibur (Ruby, Gemini) diffractometer	3012 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2873 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
Detector resolution: 10.5081 pixels mm-1	θmax = 75.9°, θmin = 4.4°
ω scans	h = −9→9
Absorption correction: analytical [CrysAlis PRO (Agilent, 2010), based on expressions derived by Clark & Reid (1995)]	k = −11→7
Tmin = 0.049, Tmax = 0.198	l = −24→25
5248 measured reflections

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)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.093	w = 1/[σ2(Fo2) + (0.0601P)2 + 0.5274P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
3012 reflections	Δρmax = 0.48 e Å−3
205 parameters	Δρmin = −0.65 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0021 (3)

Experimental. CrysAlisPro (Agilent, 2010) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)

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	0.55830 (3)	0.29987 (2)	0.362077 (11)	0.02554 (13)
Cl1	0.01337 (10)	−0.03081 (9)	0.18862 (3)	0.0433 (2)
S1	0.23124 (6)	0.09272 (5)	0.48834 (2)	0.01812 (15)
O1	0.3147 (2)	−0.03081 (17)	0.51690 (8)	0.0235 (3)
O2	0.0901 (2)	0.15202 (17)	0.51868 (8)	0.0230 (3)
O3	0.4253 (3)	0.6005 (2)	0.27820 (9)	0.0397 (5)
O4	0.5888 (3)	0.7061 (2)	0.35913 (9)	0.0352 (5)
N1	0.3799 (3)	0.2130 (2)	0.48786 (10)	0.0193 (4)
H1A	0.466 (5)	0.177 (3)	0.4775 (17)	0.027 (8)*
C1	0.3423 (3)	0.3532 (2)	0.46643 (10)	0.0185 (4)
C2	0.4146 (3)	0.4121 (2)	0.41128 (10)	0.0186 (4)
C3	0.3853 (3)	0.5527 (2)	0.39355 (11)	0.0206 (4)
C4	0.2772 (3)	0.6340 (2)	0.42946 (12)	0.0240 (4)
H4A	0.2549	0.7294	0.4170	0.029*
C5	0.2022 (3)	0.5763 (2)	0.48325 (12)	0.0229 (4)
H5A	0.1269	0.6315	0.5070	0.027*
C6	0.2372 (3)	0.4374 (3)	0.50239 (11)	0.0208 (4)
H6A	0.1890	0.3995	0.5404	0.025*
C7	0.4666 (3)	0.6198 (2)	0.33630 (11)	0.0219 (4)
C8	0.6814 (4)	0.7813 (3)	0.31100 (14)	0.0354 (6)
H8A	0.7891	0.8150	0.3326	0.053*
H8B	0.6143	0.8621	0.2936	0.053*
H8C	0.7035	0.7177	0.2742	0.053*
C9	0.1676 (3)	0.0580 (2)	0.40362 (11)	0.0203 (4)
C10	0.2808 (3)	−0.0105 (2)	0.36475 (12)	0.0233 (4)
H10A	0.3899	−0.0373	0.3835	0.028*
C11	0.2321 (3)	−0.0390 (3)	0.29849 (12)	0.0277 (5)
H11A	0.3065	−0.0871	0.2714	0.033*
C12	0.0727 (3)	0.0038 (3)	0.27216 (12)	0.0278 (5)
C13	−0.0388 (3)	0.0736 (3)	0.31041 (13)	0.0279 (5)
H13A	−0.1467	0.1028	0.2913	0.034*
C14	0.0093 (3)	0.1003 (2)	0.37711 (12)	0.0243 (5)
H14A	−0.0659	0.1473	0.4043	0.029*

	U11	U22	U33	U12	U13	U23
Br1	0.03114 (18)	0.02542 (18)	0.02113 (17)	0.00412 (8)	0.00890 (10)	0.00167 (8)
Cl1	0.0431 (4)	0.0583 (4)	0.0263 (3)	0.0072 (3)	−0.0109 (3)	−0.0104 (3)
S1	0.0171 (3)	0.0196 (3)	0.0177 (3)	0.00109 (18)	0.00194 (18)	0.00302 (17)
O1	0.0231 (8)	0.0229 (8)	0.0248 (8)	0.0032 (6)	0.0033 (6)	0.0067 (6)
O2	0.0198 (7)	0.0256 (8)	0.0242 (8)	0.0008 (6)	0.0048 (6)	0.0020 (6)
O3	0.0456 (11)	0.0525 (12)	0.0200 (8)	−0.0195 (10)	−0.0034 (8)	0.0039 (8)
O4	0.0380 (10)	0.0442 (12)	0.0223 (9)	−0.0218 (9)	−0.0036 (7)	0.0062 (7)
N1	0.0168 (9)	0.0212 (9)	0.0197 (9)	0.0014 (7)	0.0005 (7)	0.0013 (7)
C1	0.0165 (9)	0.0217 (10)	0.0165 (9)	−0.0002 (8)	−0.0034 (7)	0.0007 (8)
C2	0.0168 (9)	0.0219 (10)	0.0167 (9)	0.0008 (8)	−0.0012 (7)	−0.0017 (8)
C3	0.0189 (10)	0.0230 (10)	0.0191 (10)	−0.0012 (8)	−0.0034 (8)	0.0013 (8)
C4	0.0238 (11)	0.0201 (10)	0.0271 (11)	0.0016 (8)	−0.0042 (9)	0.0010 (8)
C5	0.0192 (10)	0.0237 (11)	0.0257 (11)	0.0024 (8)	0.0008 (8)	−0.0030 (8)
C6	0.0175 (10)	0.0248 (10)	0.0199 (10)	0.0000 (8)	0.0003 (8)	0.0000 (8)
C7	0.0226 (10)	0.0212 (10)	0.0215 (10)	0.0010 (8)	−0.0015 (8)	0.0020 (8)
C8	0.0363 (14)	0.0401 (14)	0.0296 (13)	−0.0140 (11)	0.0019 (11)	0.0088 (11)
C9	0.0208 (10)	0.0186 (10)	0.0215 (10)	−0.0017 (8)	0.0005 (8)	0.0024 (8)
C10	0.0207 (10)	0.0244 (10)	0.0243 (11)	0.0018 (8)	−0.0008 (8)	0.0013 (8)
C11	0.0286 (12)	0.0285 (11)	0.0258 (12)	0.0039 (10)	0.0019 (9)	−0.0033 (9)
C12	0.0281 (12)	0.0307 (12)	0.0238 (11)	−0.0029 (9)	−0.0042 (9)	−0.0002 (9)
C13	0.0214 (11)	0.0315 (12)	0.0297 (12)	0.0002 (9)	−0.0054 (9)	0.0010 (9)
C14	0.0206 (10)	0.0244 (11)	0.0276 (11)	0.0017 (8)	−0.0001 (9)	0.0014 (9)

Br1—C2	1.892 (2)	C4—H4A	0.9500
Cl1—C12	1.738 (3)	C5—C6	1.391 (3)
S1—O2	1.4294 (16)	C5—H5A	0.9500
S1—O1	1.4397 (16)	C6—H6A	0.9500
S1—N1	1.638 (2)	C8—H8A	0.9800
S1—C9	1.767 (2)	C8—H8B	0.9800
O3—C7	1.201 (3)	C8—H8C	0.9800
O3—Br1i	3.4022 (19)	C9—C14	1.383 (3)
O4—C7	1.320 (3)	C9—C10	1.394 (3)
O4—C8	1.446 (3)	C10—C11	1.383 (3)
N1—C1	1.418 (3)	C10—H10A	0.9500
N1—H1A	0.80 (4)	C11—C12	1.390 (4)
C1—C6	1.394 (3)	C11—H11A	0.9500
C1—C2	1.402 (3)	C12—C13	1.383 (4)
C2—C3	1.392 (3)	C13—C14	1.387 (4)
C3—C4	1.393 (3)	C13—H13A	0.9500
C3—C7	1.502 (3)	C14—H14A	0.9500
C4—C5	1.386 (3)
O2—S1—O1	119.91 (10)	C1—C6—H6A	119.7
O2—S1—N1	108.45 (10)	O3—C7—O4	124.6 (2)
O1—S1—N1	104.97 (10)	O3—C7—C3	125.4 (2)
O2—S1—C9	108.08 (10)	O4—C7—C3	109.98 (19)
O1—S1—C9	108.68 (10)	O4—C8—H8A	109.5
N1—S1—C9	105.91 (10)	O4—C8—H8B	109.5
C7—O3—Br1i	134.06 (17)	H8A—C8—H8B	109.5
C7—O4—C8	117.9 (2)	O4—C8—H8C	109.5
C1—N1—S1	121.14 (16)	H8A—C8—H8C	109.5
C1—N1—H1A	118 (2)	H8B—C8—H8C	109.5
S1—N1—H1A	110 (2)	C14—C9—C10	121.5 (2)
C6—C1—C2	118.7 (2)	C14—C9—S1	119.90 (18)
C6—C1—N1	119.76 (19)	C10—C9—S1	118.60 (17)
C2—C1—N1	121.51 (19)	C11—C10—C9	119.1 (2)
C3—C2—C1	120.81 (19)	C11—C10—H10A	120.4
C3—C2—Br1	119.86 (16)	C9—C10—H10A	120.4
C1—C2—Br1	119.31 (16)	C10—C11—C12	119.1 (2)
C2—C3—C4	119.4 (2)	C10—C11—H11A	120.5
C2—C3—C7	121.8 (2)	C12—C11—H11A	120.5
C4—C3—C7	118.8 (2)	C13—C12—C11	121.9 (2)
C5—C4—C3	120.3 (2)	C13—C12—Cl1	119.4 (2)
C5—C4—H4A	119.8	C11—C12—Cl1	118.8 (2)
C3—C4—H4A	119.8	C12—C13—C14	119.0 (2)
C4—C5—C6	120.0 (2)	C12—C13—H13A	120.5
C4—C5—H5A	120.0	C14—C13—H13A	120.5
C6—C5—H5A	120.0	C9—C14—C13	119.4 (2)
C5—C6—C1	120.7 (2)	C9—C14—H14A	120.3
C5—C6—H6A	119.7	C13—C14—H14A	120.3
O2—S1—N1—C1	−47.0 (2)	C8—O4—C7—C3	−179.6 (2)
O1—S1—N1—C1	−176.30 (17)	C2—C3—C7—O3	75.4 (3)
C9—S1—N1—C1	68.80 (19)	C4—C3—C7—O3	−104.3 (3)
S1—N1—C1—C6	64.4 (3)	C2—C3—C7—O4	−105.9 (3)
S1—N1—C1—C2	−118.6 (2)	C4—C3—C7—O4	74.3 (3)
C6—C1—C2—C3	1.4 (3)	O2—S1—C9—C14	5.6 (2)
N1—C1—C2—C3	−175.7 (2)	O1—S1—C9—C14	137.26 (19)
C6—C1—C2—Br1	179.72 (16)	N1—S1—C9—C14	−110.4 (2)
N1—C1—C2—Br1	2.6 (3)	O2—S1—C9—C10	−175.16 (17)
C1—C2—C3—C4	−2.6 (3)	O1—S1—C9—C10	−43.5 (2)
Br1—C2—C3—C4	179.04 (17)	N1—S1—C9—C10	68.8 (2)
C1—C2—C3—C7	177.6 (2)	C14—C9—C10—C11	−1.2 (4)
Br1—C2—C3—C7	−0.7 (3)	S1—C9—C10—C11	179.62 (18)
C2—C3—C4—C5	1.3 (3)	C9—C10—C11—C12	1.2 (4)
C7—C3—C4—C5	−178.9 (2)	C10—C11—C12—C13	−0.3 (4)
C3—C4—C5—C6	1.2 (3)	C10—C11—C12—Cl1	179.35 (19)
C4—C5—C6—C1	−2.5 (3)	C11—C12—C13—C14	−0.6 (4)
C2—C1—C6—C5	1.2 (3)	Cl1—C12—C13—C14	179.75 (19)
N1—C1—C6—C5	178.3 (2)	C10—C9—C14—C13	0.3 (4)
Br1i—O3—C7—O4	−27.5 (4)	S1—C9—C14—C13	179.46 (18)
Br1i—O3—C7—C3	150.97 (18)	C12—C13—C14—C9	0.6 (4)
C8—O4—C7—O3	−1.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ii	0.80 (4)	2.22 (4)	2.978 (3)	158 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.80 (4)	2.22 (4)	2.978 (3)	158 (3)

Symmetry code: (i) .