2-Hy­droxy-N-(4-methyl­phen­yl)benzamide

Abdul Rauf Raza; Bushra Nisar; M Nawaz Tahir

doi:10.1107/S1600536811030716

. 2011 Aug 6;67(Pt 9):o2253. doi: 10.1107/S1600536811030716

2-Hydroxy-N-(4-methylphenyl)benzamide

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

PMCID: PMC3200594 PMID: 22065065

Abstract

In the crystal structure of the title compound, C₁₄H₁₃NO₂, the molecules are approximately planar, the r.m.s. deviation for all non-H atoms being 0.0435 Å; the dihedral angle between the two rings is 3.45 (12)°. The planarity is accounted for in terms of the presence of intramolecular N—H⋯O and C—H⋯O hydrogen bonding, each of which completes an S(6) ring motif. The molecules are stabilized in the form of supramolecular chains extending along the crystallographic c axis due to intermolecular O—H⋯O and C—H⋯O hydrogen bonding; each type leads to an R ₂ ¹(6) ring motif.

Related literature

For related benzamide structures, see: Raza et al. (2010a ▶,b ▶,c ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₄H₁₃NO₂
M _r = 227.25
Monoclinic,
a = 19.4067 (17) Å
b = 4.9122 (5) Å
c = 12.7261 (11) Å
β = 104.793 (4)°
V = 1172.96 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.34 × 0.14 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.979, T _max = 0.988
10416 measured reflections
2771 independent reflections
1243 reflections with I > 2σ(I)
R _int = 0.060

Refinement

R[F ² > 2σ(F ²)] = 0.059
wR(F ²) = 0.159
S = 0.96
2771 reflections
156 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.16 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 datablock(s) global, I. DOI: 10.1107/S1600536811030716/tk2771sup1.cif

e-67-o2253-sup1.cif^{(20.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811030716/tk2771Isup2.hkl

e-67-o2253-Isup2.hkl^{(133.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811030716/tk2771Isup3.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
O1—H1⋯O2ⁱ	0.82	1.78	2.596 (2)	179
N1—H1A⋯O1	0.86	1.92	2.647 (2)	141
C3—H3⋯O2ⁱ	0.93	2.51	3.179 (3)	129
C9—H9⋯O2	0.93	2.25	2.840 (3)	121

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Ex-Vice Chancellor, University of Sargodha, Pakistan. ARR also acknowledges the Higher Education Commission, Government of Pakistan, for generous support of a research project (20-819).

supplementary crystallographic information

Comment

We have reported the crystal structures of (II) i.e. 2-hydroxy-N-(3-nitrophenyl)benzamide (Raza et al., 2010a), (III) i.e. N-(4-chlorophenyl)-2-hydroxybenzamide (Raza et al., 2010b) and (IV) i.e. N-(3-chlorophenyl)-2 -hydroxybenzamide (Raza et al., 2010c). In this connection, the title compound (I, Fig. 1) has been prepared as a precursor for the synthesis of symmetric as well as asymmetric benzoxazepines.

In (I), the 2-hydroxyphenyl group A (C1–C6/O1) and 4-methylanilinic group B (C8—C14/N1) are planar with r.m.s. deviations of 0.0048 and 0.0086 Å, respectively. The dihedral angle between A/B is 3.45 (12) °. There is intramolecular H-bonding of the type N—H···O and C—H···O types (Table 1, Fig. 1), each of which completes a S(6) ring motif (Bernstein et al., 1995). There is also intermolecular H-bonding of the type C—H···O and O—H···O (Table 1). These lead to the formation of two R₂¹(6) ring motifs and to supramolecular chains extending along the crystallographic c-axis (Fig. 2).

Experimental

To a well stirred solution of 2-hydroxy benzoic acid (2.76 g, 0.02 mol, 1 equiv.) and SOCl₂ (1.74 mL, 2.84 g, 0.024 mol, 1.2 equiv.) in dry CHCl₃, 4-metylaniline (2.14 g, 0.02 mol, 1 equiv.) and Et₃N (4.16 mL, 3 g, 0.03 mol, 1.5 equiv.) were added slowly at room temperature followed by 3 h reflux. After completion of reaction, the reaction mixture was cooled to room temperature, neutralized with aqueous NaHCO₃ (10 %) and extracted with CHCl₃ (3×25 mL). The organic layers were combined, dried over anhydrous Na₂SO₄, filtered and concentrated under reduced pressure to afford a brown solid. The column chromatographic purification with 1%, 2% and 3% CHCl₃ in petrol (300 mL each) over a silica gel packed column (of 25.5 cm length) afforded white needles of (I) in the 96th-280th fractions (50 mL each).