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

Zahid H Chohan; Hazoor A Shad; M Nawaz Tahir; Khalid H Thebo

doi:10.1107/S1600536809036083

. 2009 Sep 12;65(Pt 10):o2450. doi: 10.1107/S1600536809036083

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

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

PMCID: PMC2970355 PMID: 21577905

Abstract

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,
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[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 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)

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.

Supplementary Material

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

e-65-o2450-sup1.cif^{(20.4KB, cif)}

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

e-65-o2450-Isup2.hkl^{(136.8KB, hkl)}

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

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

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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.