4-{2-[(5-Bromo-2-hydroxy­benzyl­idene)amino]eth­yl}benzene­sulfonamide

Chohan, Z.H.; Shad, H.A.; Tahir, M.N.; Thebo, K.H.

doi:10.1107/S1600536809036083

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2450

doi:10.1107/S1600536809036083

Open

access

4-{2-[(5-Bromo-2-hydroxybenzylidene)amino]ethyl}benzenesulfonamide

Zahid H. Chohan,^a Hazoor A. Shad,^a M. Nawaz Tahir ^b ^* and Khalid H. Thebo ^c

^aDepartment of Chemistry, Bahauddin Zakariya University, Multan 60800, Pakistan, ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan, and ^cSchool of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, England
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 6 September 2009; accepted 7 September 2009; online 12 September 2009)

In the title compound, C₁₅H₁₅BrN₂O₃S, the dihedral angle between the benzene rings is 6.1 (2)° and an intramolecular O—H⋯N hydrogen bond helps to establish the conformation. In the crystal structure, the molecules are linked by way of N—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For related structures, see: Chohan et al. (2008 , 2009 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₅H₁₅BrN₂O₃S
M_r = 383.26
Orthorhombic, P n a 2₁
a = 50.544 (6) Å
b = 6.3146 (10) Å
c = 4.8625 (5) Å
V = 1551.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 2.80 mm⁻¹
T = 296 K
0.28 × 0.14 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.633, T_max = 0.714
8263 measured reflections
2844 independent reflections
2523 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.100
S = 1.12
2844 reflections
213 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.79 e Å⁻³
Absolute structure: Flack (1983 ), 1212 Friedel pairs
Flack parameter: 0.050 (15)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯N1	0.82	1.88	2.602 (6)	147
N2—H2A⋯O3ⁱ	0.80 (5)	2.30 (5)	3.076 (6)	163 (5)
C15—H15⋯O2ⁱⁱ	0.93	2.49	3.259 (7)	140
Symmetry codes: (i) $[-x, -y, z+{\script{1\over 2}}]$ ; (ii) x, y+1, z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809036083/hb5091sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809036083/hb5091Isup2.hkl

checkCIF report

Comment top

As part of our ongoing studies of sulfonamide derivatives (Chohan et al. 2009), we now report the preparation and crystal structure of title compound (I), (Fig. 1).

The crystal structure of (II) 4-{2-[(5-chloro-2 hydroxybenzylidene)amino]ethyl} -benzenesulfonamide (Chohan et al., 2008) has been reported which differs from (I) due to chloro substitution instead of bromo.

In (I), the benzene rings A (C1–C6) of 5-bromosalicylaldehyde and B (C10–C15) of sulfanilamide moiety are oriented at a dihedral angle of 6.1 (3)° whereas its value as observed in (II) is 23.95 (18)°. The Br1 and S1 atoms are at a distance of -0.024 (7) and -0.167 (6) Å from the mean square planes of rings A and B, respectively. There exist two intramolecular H-bondings (Table 1, Fig. 1) forming S(5) and S(6) ring motifs (Bernstein et al., 1995). Two intermolecular H-bondings (Table 1, Fig. 2) link the molecules in infinite one dimensional polymeric network extending along the c axis.

Related literature top

For related structures, see: Chohan et al. (2008, 2009). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

An ethanol solution (20 ml) of 4-(2-aminoethyl) benzene sulfonamide (0.4005 g, 2 mmol) was added to an ethanol solution (10 ml) of 5-bromosalicylaldehyde (0.402 g, 2 mmol). The reaction mixture was refluxed for 3 h. The colour of the solution gradually changed from colourless to greenish yellow. The solution was cooled to room temperature, filtered and the volume was reduced to about one-third on the rotary evaporator. The resulting mixture was allowed to stand for 10 days, after which bright yellow needles of (I) were obtained.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of (I) with displacement ellipsoids drawn at the 50% probability level. H atoms are shown by small circles of arbitrary radii. The dotted line indicate the intramolecular H-bond.
	Fig. 2. The partial packing (PLATON; Spek, 2009) which shows that molecules form polymeric chains.

4-{2-[(5-Bromo-2-hydroxybenzylidene)amino]ethyl}benzenesulfonamide top

Crystal data top

C₁₅H₁₅BrN₂O₃S	F(000) = 776
M_r = 383.26	D_x = 1.640 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2932 reflections
a = 50.544 (6) Å	θ = 2.4–28.3°
b = 6.3146 (10) Å	µ = 2.80 mm⁻¹
c = 4.8625 (5) Å	T = 296 K
V = 1551.9 (3) Å³	Needle, yellow
Z = 4	0.28 × 0.14 × 0.12 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2844 independent reflections
Radiation source: fine-focus sealed tube	2523 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 7.80 pixels mm^-1	θ_max = 25.5°, θ_min = 2.4°
ω scans	h = −52→60
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −7→6
T_min = 0.633, T_max = 0.714	l = −5→5
8263 measured reflections

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)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.100	w = 1/[σ²(F_o²) + 2.7358P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max = 0.001
2844 reflections	Δρ_max = 0.41 e Å⁻³
213 parameters	Δρ_min = −0.79 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1212 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.050 (15)

Crystal data top

C₁₅H₁₅BrN₂O₃S	V = 1551.9 (3) Å³
M_r = 383.26	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 50.544 (6) Å	µ = 2.80 mm⁻¹
b = 6.3146 (10) Å	T = 296 K
c = 4.8625 (5) Å	0.28 × 0.14 × 0.12 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2844 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2523 reflections with I > 2σ(I)
T_min = 0.633, T_max = 0.714	R_int = 0.035
8263 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.100	Δρ_max = 0.41 e Å⁻³
S = 1.12	Δρ_min = −0.79 e Å⁻³
2844 reflections	Absolute structure: Flack (1983), 1212 Friedel pairs
213 parameters	Absolute structure parameter: 0.050 (15)
1 restraint

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 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.

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

	x	y	z	U_iso*/U_eq
Br1	0.24179 (1)	0.37198 (12)	1.16449 (17)	0.0633 (2)
S1	0.03204 (2)	−0.2434 (2)	−0.5033 (3)	0.0276 (3)
O1	0.15029 (7)	0.8114 (6)	0.6129 (10)	0.0543 (16)
O2	0.04542 (7)	−0.4313 (6)	−0.5921 (8)	0.0460 (12)
O3	0.02060 (7)	−0.1032 (6)	−0.7008 (7)	0.0398 (11)
N1	0.14244 (8)	0.4653 (8)	0.3341 (10)	0.0420 (16)
N2	0.00760 (8)	−0.3200 (7)	−0.3108 (12)	0.0367 (14)
C1	0.17777 (8)	0.5013 (8)	0.6554 (13)	0.0330 (14)
C2	0.17084 (9)	0.7071 (9)	0.7344 (10)	0.0360 (17)
C3	0.18524 (10)	0.8111 (9)	0.9375 (12)	0.0437 (19)
C4	0.20599 (10)	0.7116 (9)	1.0649 (10)	0.0403 (19)
C5	0.21316 (9)	0.5108 (9)	0.9871 (12)	0.0373 (16)
C6	0.19906 (10)	0.4058 (9)	0.7859 (11)	0.0397 (17)
C7	0.16276 (10)	0.3869 (9)	0.4471 (11)	0.0390 (17)
C8	0.12783 (10)	0.3344 (9)	0.1349 (13)	0.0463 (19)
C9	0.10328 (11)	0.2403 (10)	0.2692 (11)	0.0450 (19)
C10	0.08639 (10)	0.1205 (9)	0.0700 (9)	0.0330 (16)
C11	0.09253 (10)	−0.0829 (9)	−0.0103 (12)	0.0420 (19)
C12	0.07651 (10)	−0.1935 (8)	−0.1920 (12)	0.0380 (17)
C13	0.05431 (8)	−0.0959 (7)	−0.2953 (9)	0.0263 (16)
C14	0.04792 (10)	0.1065 (8)	−0.2252 (10)	0.0323 (17)
C15	0.06412 (10)	0.2172 (9)	−0.0426 (12)	0.0403 (17)
H1O	0.14259	0.73100	0.50732	0.0815*
H2A	−0.0025 (11)	−0.224 (8)	−0.292 (14)	0.0439*
H2B	0.0123 (10)	−0.405 (9)	−0.181 (13)	0.0439*
H3	0.18077	0.94875	0.98695	0.0522*
H4	0.21522	0.78030	1.20423	0.0481*
H6	0.20392	0.26884	0.73703	0.042 (16)*
H7	0.16828	0.25207	0.39564	0.06 (2)*
H8A	0.13916	0.22125	0.06878	0.0554*
H8B	0.12268	0.42041	−0.02147	0.0554*
H9A	0.10868	0.14594	0.41624	0.0540*
H9B	0.09291	0.35359	0.35006	0.0540*
H11	0.10770	−0.14723	0.05852	0.06 (2)*
H12	0.08071	−0.33135	−0.24312	0.030 (14)*
H14	0.03291	0.17034	−0.29820	0.040 (14)*
H15	0.06003	0.35623	0.00408	0.030 (13)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0515 (3)	0.0879 (5)	0.0505 (3)	0.0203 (3)	−0.0093 (4)	−0.0043 (4)
S1	0.0311 (6)	0.0282 (6)	0.0234 (5)	−0.0029 (5)	0.0027 (5)	−0.0059 (5)
O1	0.045 (2)	0.047 (3)	0.071 (3)	0.0065 (19)	−0.013 (2)	−0.008 (2)
O2	0.047 (2)	0.036 (2)	0.055 (2)	0.0026 (18)	0.0051 (19)	−0.0254 (19)
O3	0.047 (2)	0.042 (2)	0.0305 (18)	−0.0067 (19)	−0.0041 (16)	0.0036 (17)
N1	0.030 (2)	0.052 (3)	0.044 (3)	−0.010 (2)	−0.001 (2)	−0.009 (2)
N2	0.040 (2)	0.036 (3)	0.034 (2)	−0.0072 (19)	0.005 (3)	0.002 (2)
C1	0.028 (2)	0.034 (3)	0.037 (2)	−0.007 (2)	0.010 (3)	−0.009 (3)
C2	0.028 (3)	0.037 (3)	0.043 (3)	−0.004 (2)	0.008 (2)	−0.005 (2)
C3	0.042 (3)	0.036 (3)	0.053 (4)	−0.002 (2)	−0.002 (3)	−0.008 (3)
C4	0.040 (3)	0.046 (4)	0.035 (3)	−0.011 (3)	0.004 (2)	−0.009 (2)
C5	0.025 (2)	0.052 (3)	0.035 (3)	0.003 (2)	0.008 (2)	0.003 (3)
C6	0.038 (3)	0.037 (3)	0.044 (3)	−0.003 (3)	0.008 (2)	−0.008 (3)
C7	0.036 (3)	0.040 (3)	0.041 (3)	−0.006 (2)	0.007 (2)	−0.008 (3)
C8	0.042 (3)	0.057 (4)	0.040 (3)	−0.013 (3)	−0.011 (3)	−0.011 (3)
C9	0.046 (3)	0.051 (4)	0.038 (3)	−0.013 (3)	−0.005 (2)	−0.007 (3)
C10	0.031 (2)	0.041 (3)	0.027 (3)	−0.015 (2)	0.0053 (19)	−0.004 (2)
C11	0.034 (3)	0.047 (4)	0.045 (3)	0.003 (2)	−0.010 (3)	−0.004 (3)
C12	0.042 (3)	0.025 (3)	0.047 (3)	0.004 (2)	−0.007 (3)	−0.009 (3)
C13	0.031 (2)	0.028 (3)	0.020 (3)	−0.0034 (19)	0.004 (2)	−0.003 (2)
C14	0.030 (3)	0.028 (3)	0.039 (3)	−0.002 (2)	−0.002 (2)	−0.002 (2)
C15	0.045 (3)	0.034 (3)	0.042 (3)	−0.004 (2)	0.005 (3)	−0.011 (3)

Geometric parameters (Å, º) top

Br1—C5	1.899 (5)	C9—C10	1.496 (8)
S1—O2	1.432 (4)	C10—C15	1.393 (7)
S1—O3	1.428 (4)	C10—C11	1.378 (8)
S1—N2	1.624 (5)	C11—C12	1.387 (8)
S1—C13	1.777 (4)	C12—C13	1.375 (7)
O1—C2	1.364 (6)	C13—C14	1.362 (7)
O1—H1O	0.8200	C14—C15	1.396 (7)
N1—C7	1.266 (7)	C3—H3	0.9300
N1—C8	1.472 (8)	C4—H4	0.9300
N2—H2A	0.80 (5)	C6—H6	0.9300
N2—H2B	0.86 (6)	C7—H7	0.9300
C1—C7	1.457 (8)	C8—H8A	0.9700
C1—C2	1.400 (8)	C8—H8B	0.9700
C1—C6	1.387 (7)	C9—H9A	0.9700
C2—C3	1.392 (7)	C9—H9B	0.9700
C3—C4	1.371 (7)	C11—H11	0.9300
C4—C5	1.372 (8)	C12—H12	0.9300
C5—C6	1.380 (8)	C14—H14	0.9300
C8—C9	1.523 (8)	C15—H15	0.9300

Br1···C6ⁱ	3.720 (5)	C7···C5^vi	3.479 (7)
Br1···C4ⁱⁱ	3.433 (5)	C8···C1^vi	3.594 (8)
Br1···C5ⁱⁱ	3.584 (5)	C13···O3ⁱ	3.356 (6)
Br1···H4ⁱⁱⁱ	3.1700	C14···O3ⁱ	3.188 (6)
O1···N1	2.602 (6)	C15···O2^x	3.259 (7)
O2···C15^iv	3.259 (7)	C15···O3ⁱ	3.420 (7)
O3···N2^v	3.076 (6)	C7···H1O	2.4200
O3···C14^vi	3.188 (6)	C11···H8A	3.0600
O3···C15^vi	3.420 (7)	H1O···N1	1.8800
O3···C13^vi	3.356 (6)	H1O···C7	2.4200
O2···H12	2.5400	H2A···O3^vii	2.30 (5)
O2···H15^iv	2.4900	H2B···N2^xi	2.70 (6)
O2···H9B^iv	2.7700	H4···Br1^xii	3.1700
O3···H14	2.6800	H6···H7	2.4500
O3···H2A^v	2.30 (5)	H7···H6	2.4500
O3···H14^v	2.7800	H7···H8A	2.1700
N1···O1	2.602 (6)	H8A···C11	3.0600
N2···O3^vii	3.076 (6)	H8A···H7	2.1700
N1···H1O	1.8800	H9A···H11	2.5400
N2···H2B^viii	2.70 (6)	H9B···O2^x	2.7700
C1···C4^vi	3.470 (8)	H9B···H15	2.3600
C1···C8ⁱ	3.594 (8)	H11···H9A	2.5400
C4···C1ⁱ	3.470 (8)	H12···O2	2.5400
C4···C7ⁱ	3.526 (8)	H12···H15^xiii	2.5400
C4···Br1^ix	3.433 (5)	H14···O3	2.6800
C5···C7ⁱ	3.479 (7)	H14···O3^vii	2.7800
C5···Br1^ix	3.584 (5)	H15···O2^x	2.4900
C6···Br1^vi	3.720 (5)	H15···H9B	2.3600
C7···C4^vi	3.526 (8)	H15···H12^xiv	2.5400

O2—S1—O3	120.1 (2)	S1—C13—C12	119.3 (4)
O2—S1—N2	106.6 (2)	C12—C13—C14	121.5 (4)
O2—S1—C13	107.9 (2)	S1—C13—C14	119.0 (3)
O3—S1—N2	105.3 (2)	C13—C14—C15	119.4 (5)
O3—S1—C13	108.3 (2)	C10—C15—C14	120.3 (5)
N2—S1—C13	108.1 (2)	C2—C3—H3	120.00
C2—O1—H1O	109.00	C4—C3—H3	120.00
C7—N1—C8	118.2 (5)	C3—C4—H4	120.00
S1—N2—H2A	109 (4)	C5—C4—H4	120.00
S1—N2—H2B	114 (3)	C1—C6—H6	119.00
H2A—N2—H2B	124 (6)	C5—C6—H6	119.00
C2—C1—C7	121.4 (4)	N1—C7—H7	119.00
C6—C1—C7	120.4 (5)	C1—C7—H7	119.00
C2—C1—C6	118.2 (5)	N1—C8—H8A	110.00
O1—C2—C1	121.3 (5)	N1—C8—H8B	110.00
O1—C2—C3	118.5 (5)	C9—C8—H8A	110.00
C1—C2—C3	120.1 (5)	C9—C8—H8B	110.00
C2—C3—C4	120.3 (5)	H8A—C8—H8B	108.00
C3—C4—C5	120.1 (5)	C8—C9—H9A	109.00
Br1—C5—C4	120.2 (4)	C8—C9—H9B	109.00
Br1—C5—C6	119.6 (4)	C10—C9—H9A	109.00
C4—C5—C6	120.2 (5)	C10—C9—H9B	109.00
C1—C6—C5	121.1 (5)	H9A—C9—H9B	108.00
N1—C7—C1	122.0 (5)	C10—C11—H11	119.00
N1—C8—C9	110.2 (5)	C12—C11—H11	119.00
C8—C9—C10	112.6 (4)	C11—C12—H12	121.00
C9—C10—C15	119.6 (5)	C13—C12—H12	121.00
C11—C10—C15	118.6 (5)	C13—C14—H14	120.00
C9—C10—C11	121.8 (5)	C15—C14—H14	120.00
C10—C11—C12	121.2 (5)	C10—C15—H15	120.00
C11—C12—C13	118.9 (5)	C14—C15—H15	120.00

O2—S1—C13—C12	−16.3 (5)	C2—C3—C4—C5	1.9 (8)
O2—S1—C13—C14	168.7 (4)	C3—C4—C5—Br1	−179.7 (4)
O3—S1—C13—C12	−147.7 (4)	C3—C4—C5—C6	−1.9 (8)
O3—S1—C13—C14	37.2 (4)	Br1—C5—C6—C1	178.9 (4)
N2—S1—C13—C12	98.7 (4)	C4—C5—C6—C1	1.1 (8)
N2—S1—C13—C14	−76.4 (4)	N1—C8—C9—C10	175.1 (5)
C8—N1—C7—C1	−177.3 (5)	C8—C9—C10—C11	79.5 (7)
C7—N1—C8—C9	101.1 (6)	C8—C9—C10—C15	−99.3 (6)
C6—C1—C2—O1	179.3 (5)	C9—C10—C11—C12	179.0 (5)
C6—C1—C2—C3	0.4 (8)	C15—C10—C11—C12	−2.2 (8)
C7—C1—C2—O1	−2.2 (8)	C9—C10—C15—C14	−179.0 (5)
C7—C1—C2—C3	178.8 (5)	C11—C10—C15—C14	2.3 (8)
C2—C1—C6—C5	−0.4 (8)	C10—C11—C12—C13	0.8 (8)
C7—C1—C6—C5	−178.8 (5)	C11—C12—C13—S1	−174.3 (4)
C2—C1—C7—N1	−2.0 (8)	C11—C12—C13—C14	0.6 (8)
C6—C1—C7—N1	176.4 (5)	S1—C13—C14—C15	174.4 (4)
O1—C2—C3—C4	179.9 (5)	C12—C13—C14—C15	−0.5 (7)
C1—C2—C3—C4	−1.2 (8)	C13—C14—C15—C10	−1.0 (8)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N1	0.82	1.88	2.602 (6)	147
N2—H2A···O3^vii	0.80 (5)	2.30 (5)	3.076 (6)	163 (5)
C15—H15···O2^x	0.93	2.49	3.259 (7)	140

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₅BrN₂O₃S
M_r	383.26
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	296
a, b, c (Å)	50.544 (6), 6.3146 (10), 4.8625 (5)
V (Å³)	1551.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.80
Crystal size (mm)	0.28 × 0.14 × 0.12

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.633, 0.714
No. of measured, independent and observed [I > 2σ(I)] reflections	8263, 2844, 2523
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.100, 1.12
No. of reflections	2844
No. of parameters	213
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.79
Absolute structure	Flack (1983), 1212 Friedel pairs
Absolute structure parameter	0.050 (15)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), 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
O1—H1O···N1	0.82	1.88	2.602 (6)	147
N2—H2A···O3ⁱ	0.80 (5)	2.30 (5)	3.076 (6)	163 (5)
C15—H15···O2ⁱⁱ	0.93	2.49	3.259 (7)	140

Symmetry codes: (i) −x, −y, z+1/2; (ii) x, y+1, z+1.

Acknowledgements

HAS greatfully acknowledges the Higher Education Commission, Islamabad, Pakistan, for providing a Scholarship under the Indigenous PhD Program (PIN 042-160410-PS2-117).

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chohan, Z. H., Shad, H. A. & Tahir, M. N. (2009). Acta Cryst. E65, o2426. Web of Science CSD CrossRef IUCr Journals Google Scholar
Chohan, Z. H., Shad, H. A., Tahir, M. N. & Khan, I. U. (2008). Acta Cryst. E64, o725. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar