2-(4-Bromo-benzene-sulfonamido)-2-phenyl-acetic acid monohydrate.

In the title compound, C(14)H(12)BrNO(4)S·H(2)O, the phenyl and benzene rings are inclined at a dihedral angle of 39.5 (5)°. The crystal packing is stabilized by N-H⋯O, C-H⋯O and O-H⋯O hydrogen-bonding inter-actions.

Related literature

For background to sulfonamide derivatives, see: Sheppard et al. (2006 ▶). For similar structures, see: Arshad et al. (2009 ▶); Asiri et al. (2009 ▶); Sethu Sankar et al. (2002 ▶); Wijeyesakere et al. (2008 ▶). For background to our study of the synthesis and structures of thia­zine-related heterocycles, see: Arshad et al. (2008 ▶). A related derivative has gained inter­est as a ligand in complex formation (Han et al., 2006 ▶) and for its biological activity (Cama et al., 2003 ▶; Dankwardt et al., 2002 ▶). For the synthesis, see: Deng & Mani (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H12BrNO4S·H2O

M = 388.23

Orthorhombic,

a = 5.5654 (13) Å

b = 16.230 (4) Å

c = 17.597 (4) Å

V = 1589.5 (6) Å3

Z = 4

Mo Kα radiation

μ = 2.74 mm−1

T = 296 K

0.32 × 0.11 × 0.09 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker 2007 ▶) T min = 0.474, T max = 0.791

9588 measured reflections

3315 independent reflections

1227 reflections with I > 2σ(I)

R int = 0.083

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.180

S = 0.93

3315 reflections

206 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.40 e Å−3

Absolute structure: Flack (1983 ▶), 1246 Freidel pairs

Flack parameter: 0.02 (3)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680902830X/bt5013sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902830X/bt5013Isup2.hkl

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

C14H12BrNO4S·H2O	F(000) = 784
Mr = 388.23	Dx = 1.622 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 868 reflections
a = 5.5654 (13) Å	θ = 2.3–16.4°
b = 16.230 (4) Å	µ = 2.74 mm−1
c = 17.597 (4) Å	T = 296 K
V = 1589.5 (6) Å3	Rod like, white
Z = 4	0.32 × 0.11 × 0.09 mm

Bruker Kappa APEXII CCD area-detector diffractometer	3315 independent reflections
Radiation source: sealed tube	1227 reflections with I > 2σ(I)
graphite	Rint = 0.083
φ and ω scans	θmax = 27.2°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker 2007)	h = −7→6
Tmin = 0.474, Tmax = 0.791	k = −20→17
9588 measured reflections	l = −21→14

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)] = 0.057	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.180	w = 1/[σ2(Fo2) + (0.0737P)2] where P = (Fo2 + 2Fc2)/3
S = 0.93	(Δ/σ)max < 0.001
3315 reflections	Δρmax = 0.28 e Å−3
206 parameters	Δρmin = −0.40 e Å−3
3 restraints	Absolute structure: Flack (1983), 1246 Freidel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.02 (3)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.1150 (4)	0.40711 (9)	0.42252 (7)	0.1257 (7)
S1	−0.1584 (4)	0.25772 (13)	0.74635 (12)	0.0429 (7)
O1	−0.4134 (9)	0.2431 (3)	0.7477 (3)	0.054 (2)
O2	0.0026 (9)	0.1905 (3)	0.7619 (3)	0.051 (2)
O3	0.0588 (12)	0.4809 (4)	0.7664 (4)	0.068 (3)
O4	0.4414 (11)	0.4403 (3)	0.7850 (3)	0.050 (2)
N1	−0.1125 (12)	0.3278 (4)	0.8100 (3)	0.042 (3)
C1	−0.0790 (16)	0.2999 (5)	0.6581 (4)	0.041 (3)
C2	−0.228 (2)	0.3582 (6)	0.6266 (6)	0.073 (5)
C3	−0.168 (3)	0.3924 (6)	0.5550 (6)	0.096 (6)
C4	0.041 (3)	0.3666 (6)	0.5191 (5)	0.068 (5)
C5	0.183 (2)	0.3106 (7)	0.5510 (5)	0.076 (5)
C6	0.1220 (18)	0.2760 (6)	0.6224 (5)	0.065 (4)
C7	0.1364 (15)	0.3510 (5)	0.8293 (4)	0.041 (3)
C8	0.2012 (18)	0.4313 (6)	0.7896 (5)	0.047 (4)
C9	0.1756 (17)	0.3609 (5)	0.9138 (4)	0.041 (3)
C10	0.3725 (17)	0.3299 (5)	0.9486 (5)	0.057 (4)
C11	0.412 (2)	0.3415 (7)	1.0241 (6)	0.074 (5)
C12	0.250 (2)	0.3862 (7)	1.0669 (6)	0.073 (5)
C13	0.046 (2)	0.4141 (7)	1.0329 (6)	0.073 (4)
C14	0.0096 (17)	0.4023 (6)	0.9574 (5)	0.060 (4)
O5	0.6162 (12)	0.5722 (4)	0.7272 (4)	0.064 (2)
H1	−0.23170	0.35130	0.83230	0.0510*
H2	−0.36690	0.37490	0.65180	0.0880*
H3	−0.26630	0.43160	0.53250	0.1150*
H4	0.47300	0.48030	0.75840	0.0750*
H5	0.32320	0.29420	0.52640	0.0920*
H6	0.22150	0.23670	0.64450	0.0770*
H7	0.24430	0.30770	0.81070	0.0490*
H10	0.48310	0.29990	0.92020	0.0680*
H11	0.54870	0.31930	1.04690	0.0890*
H12	0.27980	0.39700	1.11800	0.0870*
H13	−0.06900	0.44150	1.06170	0.0880*
H14	−0.12960	0.42250	0.93480	0.0720*
HW1	0.556 (19)	0.606 (7)	0.696 (7)	0.1890*
HW2	0.768 (2)	0.575 (9)	0.726 (7)	0.1890*

	U11	U22	U33	U12	U13	U23
Br1	0.2170 (18)	0.1032 (11)	0.0568 (7)	−0.0449 (12)	0.0187 (10)	0.0154 (7)
S1	0.0355 (11)	0.0463 (14)	0.0470 (13)	−0.0002 (12)	0.0066 (11)	0.0011 (12)
O1	0.028 (3)	0.058 (4)	0.076 (4)	−0.011 (3)	0.004 (3)	−0.002 (4)
O2	0.043 (3)	0.045 (4)	0.066 (4)	0.013 (3)	0.008 (3)	0.005 (3)
O3	0.049 (4)	0.055 (4)	0.101 (5)	0.011 (3)	−0.003 (4)	0.028 (4)
O4	0.043 (4)	0.043 (4)	0.065 (4)	−0.003 (3)	0.013 (3)	0.014 (3)
N1	0.026 (4)	0.059 (5)	0.042 (4)	−0.001 (4)	0.013 (3)	−0.014 (3)
C1	0.035 (6)	0.045 (6)	0.043 (5)	−0.003 (5)	0.004 (4)	−0.001 (4)
C2	0.101 (10)	0.060 (7)	0.059 (7)	0.034 (7)	0.007 (6)	0.007 (6)
C3	0.143 (13)	0.068 (8)	0.077 (9)	0.033 (9)	0.018 (9)	0.005 (7)
C4	0.122 (11)	0.042 (6)	0.041 (6)	−0.020 (7)	0.005 (7)	0.001 (5)
C5	0.063 (8)	0.111 (10)	0.054 (7)	0.009 (7)	0.015 (6)	0.005 (7)
C6	0.052 (7)	0.089 (8)	0.053 (6)	−0.007 (6)	−0.002 (5)	0.005 (6)
C7	0.030 (5)	0.039 (5)	0.055 (6)	−0.002 (4)	0.006 (4)	−0.003 (4)
C8	0.038 (7)	0.046 (7)	0.056 (6)	−0.010 (5)	0.011 (5)	−0.014 (5)
C9	0.043 (6)	0.042 (5)	0.037 (5)	−0.008 (5)	0.000 (5)	0.008 (4)
C10	0.044 (7)	0.068 (7)	0.059 (7)	0.021 (5)	0.003 (5)	0.007 (5)
C11	0.058 (8)	0.091 (8)	0.073 (8)	0.007 (7)	−0.015 (7)	0.034 (7)
C12	0.079 (9)	0.098 (10)	0.042 (6)	0.010 (6)	−0.010 (6)	0.014 (6)
C13	0.076 (8)	0.089 (8)	0.054 (7)	0.017 (7)	−0.002 (6)	−0.013 (6)
C14	0.057 (7)	0.077 (8)	0.045 (6)	0.012 (6)	−0.011 (5)	0.003 (6)
O5	0.055 (4)	0.054 (4)	0.083 (4)	−0.010 (3)	−0.007 (4)	0.014 (3)

Br1—C4	1.868 (10)	C7—C8	1.522 (12)
S1—O1	1.439 (5)	C7—C9	1.511 (10)
S1—O2	1.438 (5)	C9—C14	1.376 (13)
S1—N1	1.617 (6)	C9—C10	1.352 (13)
S1—C1	1.754 (8)	C10—C11	1.360 (14)
O3—C8	1.201 (12)	C11—C12	1.381 (16)
O4—C8	1.347 (12)	C12—C13	1.361 (16)
O4—H4	0.8200	C13—C14	1.358 (14)
O5—HW1	0.85 (11)	C2—H2	0.9300
O5—HW2	0.85 (2)	C3—H3	0.9300
N1—C7	1.475 (11)	C5—H5	0.9300
N1—H1	0.8600	C6—H6	0.9300
C1—C2	1.375 (13)	C7—H7	0.9800
C1—C6	1.340 (13)	C10—H10	0.9300
C2—C3	1.417 (15)	C11—H11	0.9300
C3—C4	1.39 (2)	C12—H12	0.9300
C4—C5	1.329 (17)	C13—H13	0.9300
C5—C6	1.418 (13)	C14—H14	0.9300
Br1···O4i	3.477 (5)	C13···H3xii	2.9500
Br1···C8i	3.660 (10)	C13···HW1v	2.94 (12)
O1···C7ii	3.377 (10)	C14···H1	2.7100
O1···O5iii	3.027 (8)	H1···H14	2.2200
O2···O5iv	2.868 (8)	H1···H10ii	2.3700
O3···N1	2.770 (9)	H1···O4ii	2.4700
O3···O5ii	2.956 (9)	H1···C10ii	3.0300
O4···O5	2.562 (8)	H1···O3	2.9000
O4···C10	3.413 (10)	H1···C14	2.7100
O4···Br1v	3.477 (5)	HW1···C13i	2.94 (12)
O4···N1vi	3.113 (9)	HW1···H12i	2.3200
O5···O3vi	2.956 (9)	HW1···C12i	2.84 (12)
O5···O2vii	2.868 (8)	HW1···H4	2.3600
O5···O1viii	3.027 (8)	HW1···O2vii	2.91 (11)
O5···O4	2.562 (8)	HW1···H13i	2.4900
O1···HW1iii	2.56 (11)	HW1···O1viii	2.56 (11)
O1···H6ii	2.7300	H2···O1	2.7400
O1···H7ii	2.4400	H2···O4ii	2.7900
O1···H2	2.7400	HW2···O3vi	2.34 (10)
O2···H7	2.4800	HW2···O2vii	2.28 (12)
O2···H6	2.5100	HW2···H4	2.3200
O2···HW1iv	2.91 (11)	H3···H13x	2.3100
O2···H12ix	2.8300	H3···C13x	2.9500
O2···HW2iv	2.28 (12)	H4···HW2	2.3200
O3···HW2ii	2.34 (10)	H4···O5	1.7800
O3···H1	2.9000	H4···HW1	2.3600
O4···H2vi	2.7900	H5···C5xiii	2.9600
O4···H1vi	2.4700	H5···C4xiii	2.9900
O5···H4	1.7800	H6···O1vi	2.7300
N1···O4ii	3.113 (9)	H6···O2	2.5100
N1···O3	2.770 (9)	H7···O1vi	2.4400
N1···H14	2.6800	H7···O2	2.4800
C1···C8	3.512 (12)	H7···H10	2.3400
C7···O1vi	3.377 (10)	H10···H1vi	2.3700
C8···Br1v	3.660 (10)	H10···H7	2.3400
C8···C1	3.512 (12)	H11···C9xiv	3.0900
C10···O4	3.413 (10)	H11···C10xiv	3.0200
C3···H13x	3.0700	H12···HW1v	2.3200
C4···H5xi	2.9900	H12···O2xiv	2.8300
C5···H5xi	2.9600	H13···C3xii	3.0700
C9···H11ix	3.0900	H13···HW1v	2.4900
C10···H1vi	3.0300	H13···H3xii	2.3100
C10···H11ix	3.0200	H14···N1	2.6800
C12···HW1v	2.84 (12)	H14···H1	2.2200
O1—S1—O2	119.1 (3)	C7—C9—C14	120.2 (8)
O1—S1—N1	105.1 (3)	C10—C9—C14	118.2 (7)
O1—S1—C1	109.1 (4)	C9—C10—C11	121.5 (9)
O2—S1—N1	107.7 (3)	C10—C11—C12	120.0 (10)
O2—S1—C1	107.9 (4)	C11—C12—C13	118.7 (10)
N1—S1—C1	107.4 (4)	C12—C13—C14	120.5 (10)
C8—O4—H4	109.00	C9—C14—C13	121.0 (9)
HW1—O5—HW2	110 (12)	C3—C2—H2	120.00
S1—N1—C7	119.2 (5)	C1—C2—H2	121.00
C7—N1—H1	120.00	C2—C3—H3	121.00
S1—N1—H1	120.00	C4—C3—H3	120.00
S1—C1—C6	120.8 (7)	C4—C5—H5	120.00
S1—C1—C2	118.3 (7)	C6—C5—H5	120.00
C2—C1—C6	120.9 (8)	C5—C6—H6	120.00
C1—C2—C3	119.1 (10)	C1—C6—H6	120.00
C2—C3—C4	119.0 (11)	C8—C7—H7	108.00
Br1—C4—C5	119.6 (10)	C9—C7—H7	108.00
C3—C4—C5	120.8 (9)	N1—C7—H7	108.00
Br1—C4—C3	119.5 (9)	C11—C10—H10	119.00
C4—C5—C6	120.2 (10)	C9—C10—H10	119.00
C1—C6—C5	120.1 (9)	C10—C11—H11	120.00
N1—C7—C9	112.9 (6)	C12—C11—H11	120.00
C8—C7—C9	109.1 (7)	C13—C12—H12	121.00
N1—C7—C8	109.6 (7)	C11—C12—H12	121.00
O3—C8—O4	124.2 (9)	C12—C13—H13	120.00
O3—C8—C7	125.0 (9)	C14—C13—H13	120.00
O4—C8—C7	110.8 (7)	C9—C14—H14	120.00
C7—C9—C10	121.5 (8)	C13—C14—H14	120.00
O1—S1—N1—C7	173.4 (5)	C3—C4—C5—C6	0.3 (17)
O2—S1—N1—C7	45.5 (6)	C4—C5—C6—C1	−0.2 (16)
C1—S1—N1—C7	−70.5 (6)	N1—C7—C8—O3	21.3 (12)
O1—S1—C1—C2	40.8 (8)	N1—C7—C8—O4	−159.8 (6)
O2—S1—C1—C2	171.6 (7)	C9—C7—C8—O3	−102.8 (10)
N1—S1—C1—C2	−72.6 (8)	C9—C7—C8—O4	76.1 (9)
O1—S1—C1—C6	−139.3 (7)	N1—C7—C9—C10	136.2 (8)
O2—S1—C1—C6	−8.6 (8)	N1—C7—C9—C14	−43.9 (11)
N1—S1—C1—C6	107.3 (8)	C8—C7—C9—C10	−101.7 (9)
S1—N1—C7—C8	101.1 (7)	C8—C7—C9—C14	78.2 (10)
S1—N1—C7—C9	−137.1 (6)	C7—C9—C10—C11	177.5 (9)
S1—C1—C6—C5	179.8 (7)	C14—C9—C10—C11	−2.4 (14)
S1—C1—C2—C3	−179.4 (8)	C7—C9—C14—C13	−177.8 (9)
C6—C1—C2—C3	0.7 (15)	C10—C9—C14—C13	2.1 (14)
C2—C1—C6—C5	−0.3 (14)	C9—C10—C11—C12	−0.4 (16)
C1—C2—C3—C4	−0.7 (16)	C10—C11—C12—C13	3.5 (17)
C2—C3—C4—C5	0.2 (18)	C11—C12—C13—C14	−3.8 (17)
C2—C3—C4—Br1	177.0 (8)	C12—C13—C14—C9	1.0 (16)
Br1—C4—C5—C6	−176.5 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4ii	0.86	2.47	3.113 (9)	132
O5—HW1···O1viii	0.85 (11)	2.56 (11)	3.027 (8)	116 (10)
O5—HW2···O3vi	0.85 (2)	2.34 (10)	2.956 (9)	131 (12)
O5—HW2···O2vii	0.85 (2)	2.28 (12)	2.868 (8)	127 (12)
O4—H4···O5	0.82	1.78	2.562 (8)	160
C6—H6···O2	0.93	2.51	2.897 (10)	105
C7—H7···O1vi	0.98	2.44	3.377 (10)	160
C7—H7···O2	0.98	2.48	2.958 (9)	109

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4i	0.86	2.47	3.113 (9)	132
O5—HW1⋯O1ii	0.85 (11)	2.56 (11)	3.027 (8)	116 (10)
O5—HW2⋯O3iii	0.85 (2)	2.34 (10)	2.956 (9)	131 (12)
O5—HW2⋯O2iv	0.85 (2)	2.28 (12)	2.868 (8)	127 (12)
O4—H4⋯O5	0.82	1.78	2.562 (8)	160
C6—H6⋯O2	0.93	2.51	2.897 (10)	105
C7—H7⋯O1iii	0.98	2.44	3.377 (10)	160
C7—H7⋯O2	0.98	2.48	2.958 (9)	109

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