{2-[(3-Bromo­benzyl­idene)amino]-5-chloro­phen­yl}(phen­yl)methanone

M Aslam; I Anis; N Afza; M Safder; S Yousuf

doi:10.1107/S1600536812004667

. 2012 Feb 10;68(Pt 3):o645. doi: 10.1107/S1600536812004667

{2-[(3-Bromobenzylidene)amino]-5-chlorophenyl}(phenyl)methanone

M Aslam ^a,^b,^‡, I Anis ^b, N Afza ^a, M Safder ^c, S Yousuf ^c,^*

PMCID: PMC3295437 PMID: 22412548

Abstract

In the title compound, C₂₀H₁₃BrClNO, the azomethine double bond [C=N = 1.246 (4) Å] adopts an E conformation. The bromo- and chlorophenyl rings are inclined to one another by 13.70 (11)°, and form dihedral angles of 76.68 (10) and 74.24 (7)°, respectively, with the phenyl ring. In the crystal, molecules are linked by C—H⋯O hydrogen bonds to form double stranded chains propagating along the b-axis direction.

Related literature

For background information and preparation of Schiff bases, see: Khan et al. (2009 ▶); Aslam et al. (2011a ▶,b ▶); Zeb & Yousuf (2011 ▶). For the crystal structures of related Schiff bases, see: Aslam et al. (2011a ▶,b ▶); Cox et al. (2008 ▶).

Experimental

Crystal data

C₂₀H₁₃BrClNO
M _r = 398.67
Orthorhombic,
a = 16.2068 (12) Å
b = 7.8839 (6) Å
c = 27.262 (2) Å
V = 3483.4 (5) Å³
Z = 8
Mo Kα radiation
μ = 2.52 mm⁻¹
T = 273 K
0.52 × 0.21 × 0.15 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.354, T _max = 0.704
19261 measured reflections
3243 independent reflections
1931 reflections with I > 2σ(I)
R _int = 0.056

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.115
S = 1.01
3243 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.64 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; 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, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812004667/pv2506sup1.cif

e-68-0o645-sup1.cif^{(19.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004667/pv2506Isup2.hkl

e-68-0o645-Isup2.hkl^{(159.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812004667/pv2506Isup3.cml

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
C12—H12A⋯O1ⁱ	0.93	2.44	3.346 (4)	166
C17—H17A⋯O1ⁱⁱ	0.93	2.51	3.428 (5)	168

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

Acknowledgments

MA express his gratitude to the Pakistan Council of Scientific and Industrial Research Laboratories, Karachi, the Department of Chemistry, University of Karachi, and the HEJ Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, for providing financial support, research facilities and X-ray diffraction facilities, respectively.

supplementary crystallographic information

Comment

The title compound was prepared as a part of our ongoing reasearch on schiff bases (Khan et al., 2009; Aslam et al., 2011a,b; Zeb & Yousuf, 2011).

In the title compound (Fig. 1), the azomethine double bond (C═N, 1.246 (4) Å) adopts an E configuration with torsion angle C6—C7—N1—C8 174.9 (3)°. The bond lengths and angle are similar as in other structurally realted compounds (Aslam et al., 2011a,b; Cox et al., 2008). In the crystal structure the molecules are arranged in parallel sheets along the b-axis via C—H···O type intermolecular hydrogen bonds (Fig. 2).

Experimental

A mixture of 3-bromobenzaldehyde (1 mol) and 2-amino-5-chlorobenzophenone (1 mol) in ethanol (50 ml) along with 3 drops of conc. H₂SO₄ was refluxed for 5 h at 343 K. After cooling, the mixture was concentrated to one third under reduced pressure. The concentrated reaction mixture was kept at room temperature and orange red crystals were obtained after five days. The crystalline product was collected, washed with methanol and dried to afford the title compound in 87% yield. Slow evaporation of a methanol solution afforded yellow crystals suitable for single-crystal X-ray diffraction studies. All chemicals were purchased from Sigma-Aldrich.