2-(4-Bromo­benzene­sulfonamido)-2-phenyl­acetic acid monohydrate

Arshad, M.N.; Khan, I.U.; Akkurt, M.; Shafiq, M.

doi:10.1107/S160053680902830X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Pages o1953-o1954

doi:10.1107/S160053680902830X

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2-(4-Bromobenzenesulfonamido)-2-phenylacetic acid monohydrate

Muhammad Nadeem Arshad,^a Islam Ullah Khan,^a Mehmet Akkurt ^b ^* and Muhammad Shafiq ^a

^aDepartment of Chemistry, Government College University, Lahore, Pakistan, and ^bDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 17 July 2009; accepted 17 July 2009; online 22 July 2009)

In the title compound, C₁₄H₁₂BrNO₄S·H₂O, 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 interactions.

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_r = 388.23
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.057
wR(F²) = 0.180
S = 0.93
3315 reflections
206 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.40 e Å⁻³
Absolute structure: Flack (1983 ), 1246 Freidel pairs
Flack parameter: 0.02 (3)

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⋯O2^iv	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) x-1, y, z; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) x+1, y, z; (iv) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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 ).

Supporting information

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

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

checkCIF report

Comment top

The title compound was synthesized via condensation reaction between 4-bromo benzene sulfonylchloride and phenylglycine, an amino acid. The related derivative has gained interest as a ligand in complexation (Han et al., 2006) and biological activities (Dankwardt et al., 2002, Cama et al., 2003). It is the halogenated analogue of previously reported sulfonamide derivative of phenylglycine (Arshad et al., 2009) in continuation of synthesis and crystal structure studies of thiazine related heterocycles (Arshad et al., 2008).

In the title compound (Fig. 1), the Br—C and C—O distances are as expected. The S—C_benzene distance of 1.754 (8) Å is shorter than the reported values of 1.763 (2)Å (Asiri et al., 2009) and 1.763 (9) Å (Allen et al., 1987). The S1—N1 distance of 1.617 (6) is shorter than the literature values of 1.6213 (18) Å (Asiri et al., 2009) and 1.6458 (11) Å (Wijeyesakere et al., 2008). The mean S=O distance of 1.439 (5) Å is comparable with the reported value of 1.436 (2) Å (Sethu Sankar et al., 2002). The interplanar angle between the phenyl (C9–C14) and benzene (C1–C6) rings in (I) is 39.5 (5) °. These rings orient to the carbonyl group (C7/C8/O3/O4) with angles of 41.5 (5) and 77.1 (5) °, respectively.

The crystal packing is stabilized by N—H···O, C—H···O and O—H···O hydrogen bonding interactions (Table 1, Fig. 2).

Related literature top

derivative has gained interest as a ligand in complexation (Han et al., 2006) and for its biolgical activity (Cama et al., 2003; Dankwardt et al., 2002). For the synthesis, see: Deng & Mani (2006); For bond-lengths data, see: Allen et al. (1987).

Experimental top

The title compound was prepared in accordance with the literature method (Deng & Mani, 2006). Phenylglycine (1 g, 6.6 mmol) was dissolved in distilled water (10 ml) using 1M, Na₂CO₃solution at pH 8–9. 4-Bromo benzene sulfonyl chloride (1.68 g, 6.6 mmol) was then added to the solution, which was stirred at room temperature until all the 4-bromobenzene sulfonyl chloride had been consumed. On completion of the reaction the pH was adjusted to 1–2, using 1 N HCl with stirring. The precipitate obtained was filtered, washed with distilled water, dried and recrystalized in methanol for X-ray diffraction studies.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top

	Fig. 1. The molecular structure of (I), showing the atom labeling scheme and displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. View of the crystal packing and hydrogen bonding (dashed lines) of the title compound, down the a-axis. H atoms not involved in the hydrogen bonding have been omitted for clarity.

2-(4-Bromobenzenesulfonamido)-2-phenylacetic acid monohydrate top

Crystal data top

C₁₄H₁₂BrNO₄S·H₂O	F(000) = 784
M_r = 388.23	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0737P)²] where P = (F_o² + 2F_c²)/3
S = 0.93	(Δ/σ)_max < 0.001
3315 reflections	Δρ_max = 0.28 e Å⁻³
206 parameters	Δρ_min = −0.40 e Å⁻³
3 restraints	Absolute structure: Flack (1983), 1246 Freidel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (3)

Crystal data top

C₁₄H₁₂BrNO₄S·H₂O	V = 1589.5 (6) Å³
M_r = 388.23	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.5654 (13) Å	µ = 2.74 mm⁻¹
b = 16.230 (4) Å	T = 296 K
c = 17.597 (4) Å	0.32 × 0.11 × 0.09 mm

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	3315 independent reflections
Absorption correction: multi-scan (SADABS; Bruker 2007)	1227 reflections with I > 2σ(I)
T_min = 0.474, T_max = 0.791	R_int = 0.083
9588 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.180	Δρ_max = 0.28 e Å⁻³
S = 0.93	Δρ_min = −0.40 e Å⁻³
3315 reflections	Absolute structure: Flack (1983), 1246 Freidel pairs
206 parameters	Absolute structure parameter: 0.02 (3)
3 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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···H3^xii	2.9500
Br1···C8ⁱ	3.660 (10)	C13···HW1^v	2.94 (12)
O1···C7ⁱⁱ	3.377 (10)	C14···H1	2.7100
O1···O5ⁱⁱⁱ	3.027 (8)	H1···H14	2.2200
O2···O5^iv	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···Br1^v	3.477 (5)	HW1···C13ⁱ	2.94 (12)
O4···N1^vi	3.113 (9)	HW1···H12ⁱ	2.3200
O5···O3^vi	2.956 (9)	HW1···C12ⁱ	2.84 (12)
O5···O2^vii	2.868 (8)	HW1···H4	2.3600
O5···O1^viii	3.027 (8)	HW1···O2^vii	2.91 (11)
O5···O4	2.562 (8)	HW1···H13ⁱ	2.4900
O1···HW1ⁱⁱⁱ	2.56 (11)	HW1···O1^viii	2.56 (11)
O1···H6ⁱⁱ	2.7300	H2···O1	2.7400
O1···H7ⁱⁱ	2.4400	H2···O4ⁱⁱ	2.7900
O1···H2	2.7400	HW2···O3^vi	2.34 (10)
O2···H7	2.4800	HW2···O2^vii	2.28 (12)
O2···H6	2.5100	HW2···H4	2.3200
O2···HW1^iv	2.91 (11)	H3···H13^x	2.3100
O2···H12^ix	2.8300	H3···C13^x	2.9500
O2···HW2^iv	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···H2^vi	2.7900	H5···C5^xiii	2.9600
O4···H1^vi	2.4700	H5···C4^xiii	2.9900
O5···H4	1.7800	H6···O1^vi	2.7300
N1···O4ⁱⁱ	3.113 (9)	H6···O2	2.5100
N1···O3	2.770 (9)	H7···O1^vi	2.4400
N1···H14	2.6800	H7···O2	2.4800
C1···C8	3.512 (12)	H7···H10	2.3400
C7···O1^vi	3.377 (10)	H10···H1^vi	2.3700
C8···Br1^v	3.660 (10)	H10···H7	2.3400
C8···C1	3.512 (12)	H11···C9^xiv	3.0900
C10···O4	3.413 (10)	H11···C10^xiv	3.0200
C3···H13^x	3.0700	H12···HW1^v	2.3200
C4···H5^xi	2.9900	H12···O2^xiv	2.8300
C5···H5^xi	2.9600	H13···C3^xii	3.0700
C9···H11^ix	3.0900	H13···HW1^v	2.4900
C10···H1^vi	3.0300	H13···H3^xii	2.3100
C10···H11^ix	3.0200	H14···N1	2.6800
C12···HW1^v	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)

Symmetry codes: (i) −x+1/2, −y+1, z−1/2; (ii) x−1, y, z; (iii) −x, y−1/2, −z+3/2; (iv) −x+1, y−1/2, −z+3/2; (v) −x+1/2, −y+1, z+1/2; (vi) x+1, y, z; (vii) −x+1, y+1/2, −z+3/2; (viii) −x, y+1/2, −z+3/2; (ix) x−1/2, −y+1/2, −z+2; (x) −x−1/2, −y+1, z−1/2; (xi) x−1/2, −y+1/2, −z+1; (xii) −x−1/2, −y+1, z+1/2; (xiii) x+1/2, −y+1/2, −z+1; (xiv) x+1/2, −y+1/2, −z+2.

Hydrogen-bond geometry (Å, º) top

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···O1^viii	0.85 (11)	2.56 (11)	3.027 (8)	116 (10)
O5—HW2···O3^vi	0.85 (2)	2.34 (10)	2.956 (9)	131 (12)
O5—HW2···O2^vii	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···O1^vi	0.98	2.44	3.377 (10)	160
C7—H7···O2	0.98	2.48	2.958 (9)	109

Symmetry codes: (ii) x−1, y, z; (vi) x+1, y, z; (vii) −x+1, y+1/2, −z+3/2; (viii) −x, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂BrNO₄S·H₂O
M_r	388.23
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	5.5654 (13), 16.230 (4), 17.597 (4)
V (Å³)	1589.5 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.74
Crystal size (mm)	0.32 × 0.11 × 0.09

Data collection
Diffractometer	Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker 2007)
T_min, T_max	0.474, 0.791
No. of measured, independent and observed [I > 2σ(I)] reflections	9588, 3315, 1227
R_int	0.083
(sin θ/λ)_max (Å⁻¹)	0.644

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.180, 0.93
No. of reflections	3315
No. of parameters	206
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.40
Absolute structure	Flack (1983), 1246 Freidel pairs
Absolute structure parameter	0.02 (3)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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···O2^iv	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) x−1, y, z; (ii) −x, y+1/2, −z+3/2; (iii) x+1, y, z; (iv) −x+1, y+1/2, −z+3/2.

Acknowledgements

MNA acknowledges the Higher Education Commission of Pakistan for providing a PhD Scholarship under the Indiginous 5000 PhD fellowship Programme (No. 042–120607-PS2–183).

References

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