N-(3-Chloro­phen­yl)-2-hy­droxy­benzamide

Abdul Rauf Raza; Bushra Nisar; M Nawaz Tahir; Sumaira Shamshad

doi:10.1107/S1600536810045046

. 2010 Nov 6;66(Pt 12):o3100. doi: 10.1107/S1600536810045046

N-(3-Chlorophenyl)-2-hydroxybenzamide

Abdul Rauf Raza ^a, Bushra Nisar ^a, M Nawaz Tahir ^b,^*, Sumaira Shamshad ^a

PMCID: PMC3011749 PMID: 21589406

Abstract

In the title compound, C₁₃H₁₀ClNO₂, the dihedral angle between the aromatic rings is 5.57 (9)° and intramolecular N—H⋯O and C—H⋯O hydrogen bonds both generate S(6) rings. In the crystal, molecules are linked by O—H⋯O hydrogen bonds into C(6) chains propagating along [010]. Molecules from neighbouring chains along the z axis are involved in C—H⋯π and π–π stacking interactions [centroid–centroid distance = 3.9340 (10) Å].

Related literature

For pharmacological background to this work, see: Coupet et al. (1979 ▶); Pae et al. (2004 ▶). For related structures, see: Raza et al. (2009 ▶, 2010a ▶,b ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₃H₁₀ClNO₂
M _r = 247.67
Monoclinic,
a = 13.4638 (5) Å
b = 11.9019 (4) Å
c = 7.1764 (2) Å
β = 98.808 (2)°
V = 1136.42 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 296 K
0.24 × 0.16 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.982, T _max = 0.987
10332 measured reflections
2806 independent reflections
1827 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.115
S = 1.03
2806 reflections
161 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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/S1600536810045046/gk2313sup1.cif

e-66-o3100-sup1.cif^{(16.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045046/gk2313Isup2.hkl

e-66-o3100-Isup2.hkl^{(137.8KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.88 (2)	1.73 (2)	2.6016 (18)	173 (2)
N1—H1A⋯O1	0.88 (2)	1.85 (2)	2.606 (2)	143.4 (18)
C13—H13⋯O2	0.93	2.30	2.869 (2)	119
C6—H6⋯Cg1ⁱⁱ	0.93	2.89	3.675 (2)	143

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

Acknowledgments

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

supplementary crystallographic information

Comment

Benzoxazepines are known for their mild tranquilizing activities. Different synthetic derivatives of benzoxazepine are potential biological candidates and exhibit a wide range of biological activities, e.g., anti-inflammatory activity (Pae et al., 2004), anti-depressant and anti-psychotic activity (Coupet et al., 1979). The title compound (I, Fig. 1) has been prepared as a precursor for the asymmetric synthesis of benzoxazepines.

We have reported the crystal structures of (II) i.e., N-(4-chlorophenyl) -2-hydroxybenzamide (Raza et al., 2010a), (III) 2-hydroxy-5-nitro -N-phenylbenzamide (Raza et al., 2010b) and (IV) 2-hydroxy-3-nitro-N-phenylbenzamide (Raza et al., 2009) which are related to the title compound. The title compound differs from (II) due to attachment of chloro group at position-3 instead of position-4.

In (I), the phenyl rings A (C1–C6) of 2-hydroxyphenyl is planar with r. m. s. deviation of 0.012 Å and the O-atom of hydroxy group [O1] is at a distance of -0.078 (2) Å. Similary the phenyl ring B (C8—C13) of 3-chloroanilinic group is planar with r. m. s. deviation of 0.004 Å and the chloro group [CL1] is at a distance of -0.076 (2) Å. The dihedral angle between A/B is 5.57 (9)°. There exist intramolecular H-bonds of N—H···O and C—H···O types (Table 1, Fig. 1) completing S(6) ring motifs (Bernstein et al., 1995). The molecules are arranged to form one dimensional polymeric chains extending along the crystallographic b axis due to intermolecular H-bonds of O—H···O type (Table 1, Fig. 2). The C—H···π interactions (Table 1) and π–π interactions [the centroids of both aromatic rings at a distance of 3.934 (10) Å (symmetry: 1 - x, - y, 1 - z)] play an important role in stabilization of the crystal.

Experimental

To a well stirred solution of 2-hydroxybenzoic acid (1.38 g, 0.01 mol, 1 eq) and SOCl₂ (0.87 ml, 1.42 g, 0.012 mol, 1.2 eq) in dry CHCl₃, 3-chloroaniline (1.05 ml, 1.27 g, 0.01 mol, 1 eq) and Et₃N (2.08 ml, 1.5 g, 0.015 mol, 1.5 eq) was added slowly at room temperature, followed by reflux for three hours. After the completion of the reaction, the reaction mixture was cooled to room temperature, neutralized with aqueous NaHCO₃ (10%) and the title compound was obtained as a white solid. The crude solid was filtered off and recrystallized from CHCl₃ to afford white prisms.