2-Methyl-4-(2-methyl­benzamido)­benzoic acid

Fei-Fei He; Ya-Bin Shi; Song Xia; Hai-Bo Wang

doi:10.1107/S160053681101110X

. 2011 Apr 7;67(Pt 5):o1050. doi: 10.1107/S160053681101110X

2-Methyl-4-(2-methylbenzamido)benzoic acid

Fei-Fei He ^a,^b, Ya-Bin Shi ^a,^b, Song Xia ^a,^b, Hai-Bo Wang ^a,^*

PMCID: PMC3089156 PMID: 21754377

Abstract

In the crystal structure of the title compound, C₁₆H₁₅NO₃, intermolecular N—H⋯O hydrogen bonds link the molecules into chains parallel to the b axis and pairs of intermolecular O—H⋯O hydrogen bonds between inversion-related carboxylic acid groups link the molecules into dimers. The dihedral angle between the two benzene rings is 82.4 (2)°.

Related literature

For the use of the title compound as an intermediate in the preparation of pharmaceutically active benzazepine compounds that have vasopressin antagonistic activity, see: Yasuhiro et al. (2007 ▶). For the preparation of the title compound, see: Yasuhiro et al. (2000 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₆H₁₅NO₃
M _r = 269.29
Monoclinic,
a = 23.318 (9) Å
b = 10.230 (2) Å
c = 13.901 (3) Å
β = 125.50 (3)°
V = 2699.7 (16) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.982, T _max = 0.991
4968 measured reflections
2493 independent reflections
1641 reflections with I > 2σ(I)
R _int = 0.034
3 standard reflections every 120 min intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.138
S = 1.00
2493 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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: PLATON (Spek, 2009) ▶.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681101110X/pk2306sup1.cif

e-67-o1050-sup1.cif^{(18.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681101110X/pk2306Isup2.hkl

e-67-o1050-Isup2.hkl^{(122.6KB, 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
N—H0A⋯O1ⁱ	0.86	2.23	3.076 (3)	169
O2—H2A⋯O3ⁱⁱ	0.82	1.82	2.636 (4)	174

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

supplementary crystallographic information

Comment

The title compound, 2-methyl-4-(2-methylbenzamido)benzoic acid, or salts thereof are useful as intermediates for preparing pharmaceutically active benzazepine compounds that have vasopressin antagonistic activity. (Yasuhiro et al. 2007).

In the molecule of 2-methyl-4-(2-methylbenzamido)benzoic acid (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Intermolecular N-H···O hydrogen bonds link the molecules parallel to the b axis and pairs of intermolecular N-H···O hydrogen bonds link the molecules parallel to the b axis and pairs of intermolecular O-H···O hydrogen bonds between inversion related (x,y,z & 1-x,2-y,-z) carboxylic acid groups link the molecules into dimers. The dihedral angle between the two benzene rings is 82.39 (19) ° (Fig. 2).

Experimental

The title compound, 2-methyl-4-(2-methylbenzamido)benzoic acid was prepared by the literature method (Yasuhiro et al. 2000). Recrystallization of the of the crude crystalline product gave a yield of 81%. Crystals suitable for X-ray analysis were obtained by slow evaporation of a solution in methanol.