Crystal structure of N-(2-hy­droxy-5-methyl­phen­yl)benzamide

Rodolfo Moreno-Fuquen; Nory J Mariño; Alan R Kennedy

doi:10.1107/S2056989015020575

. 2015 Nov 14;71(Pt 12):o943. doi: 10.1107/S2056989015020575

Crystal structure of N-(2-hydroxy-5-methylphenyl)benzamide

Rodolfo Moreno-Fuquen ^a,^*, Nory J Mariño ^a, Alan R Kennedy ^b

PMCID: PMC4719913 PMID: 26870541

Abstract

In the title compound, C₁₄H₁₃NO₂, the mean plane of the non-H atoms of the central amide fragment C—N—C(=O)—C (r.m.s. deviation = 0.029 Å) forms dihedral angles of 5.63 (6) and 10.20 (5)° with the phenyl and hydroxyphenyl rings, respectively. A short intramolecular N—H⋯O contact is present. In the crystal, the molecules are linked by O—H⋯O hydrogen bonds to generate C(7) chains along [100]. The chains are reinforced by weak C—H⋯O contacts, which together with the O—H⋯O bonds lead to R ₂ ²(7) loops. Very weak N—H⋯O interactions link the molecules into inversion dimers.

Keywords: crystal structure, benzamide, benzanilide derivatives, biological activity

Related literature

For the biological activity of benzanilide derivatives, see Calderone et al. (2006 ▸). For related structures, see: Gowda et al. (2008 ▸); Rodrigues et al. (2011 ▸).

Experimental

Crystal data

C₁₄H₁₃NO₂
M _r = 227.25
Monoclinic,
a = 7.2263 (3) Å
b = 21.7442 (7) Å
c = 7.4747 (3) Å
β = 110.280 (5)°
V = 1101.69 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 123 K
0.40 × 0.35 × 0.25 mm

Data collection

Oxford Diffraction Gemini S CCD diffractometer
10254 measured reflections
2795 independent reflections
2332 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.109
S = 1.03
2795 reflections
163 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▸); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and Mercury (Macrae et al., 2006 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015020575/hb7532sup1.cif

e-71-0o943-sup1.cif^{(358.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015020575/hb7532Isup2.hkl

e-71-0o943-Isup2.hkl^{(223.6KB, hkl)}

Click here for additional data file.^{(4.6KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015020575/hb7532Isup3.cml

Click here for additional data file.^{(1.1MB, tif)}

. DOI: 10.1107/S2056989015020575/hb7532fig1.tif

The molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitrary radius.

Click here for additional data file.^{(1.4MB, tif)}

x y z x y z . DOI: 10.1107/S2056989015020575/hb7532fig2.tif

Part of the crystal structure of (I), showing the formation of C(7) chains of molecules along [100] [Symmetry codes: (i) x + 1, +y, +z; (ii) x − 1, +y, +z].

Click here for additional data file.^{(900.3KB, tif)}

x y z . DOI: 10.1107/S2056989015020575/hb7532fig3.tif

Part of the crystal structure of (I), showing the formation of dimers along [001]. [Symmetry codes: (iii) −x + 1, −y, −z + 1].

CCDC reference: 1434264

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.889 (18)	2.173 (16)	2.6153 (15)	110.0 (13)
N1—H1⋯O2ⁱ	0.889 (18)	2.518 (17)	3.1928 (14)	133.1 (14)
O2—H20⋯O1ⁱⁱ	0.89 (2)	1.75 (2)	2.6390 (12)	171.3 (19)
C6—H6⋯O2ⁱⁱⁱ	0.95	2.59	3.4197 (15)	146

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

Acknowledgments

RMF is grateful to the Universidad del Valle, Colombia, for partial financial support.

supplementary crystallographic information

S1. Comment

The crystal structure determination of N-(2-hydroxy-5-methylphenyl)benzamide (I), is part of a study on phenylbenzamides carried out in our research group, and it was synthesized from the reaction between of 2-amino-4-methylphenol and benzoyl chloride in acetonitrile. Benzanilide systems have a wide range of biological properties such as potassium channel activators (Calderone et al., 2006). Similar compounds to (I) have been reported in the literature: 2-Methyl-N-(m-tolyl)benzamide (II) (Gowda et al., 2008) and N-(3,5-Dimethylphenyl)-4-methylbenzamide (III) (Rodrigues et al., 2011). The molecular structure of (I) is shown in Fig. 1. The central amide moiety, C8—N1-C7(═O1)—C1, is close to planar (r.m.s. deviation for all non-H atoms = 0.0291 Å) and it forms dihedral angles of 5.63 (6)° with the C1-C6 and 10.20 (5)° with the C8-C13 rings respectively. Bond lengths and bond angles in the molecule are in a good agreement with those found in the related compounds (II) and (III). The conformation of the N—H group is syn to the –OH substituent in the benzoyl ring, which results in a short intramolecular N—H···O contact. In the crystal (Fig. 2), molecules are linked by strong O-H···O hydrogen bonds and weak C-H···O intermolecular contacts. Indeed, the O2-H20 at (x,y,z) acts as a hydrogen-bond donor to O1 atom of the carbonyl group at (x+1,+y,+z) and the C6-H6 acts as a hydrogen-bond donor to O2 atom of the hydroxyl group at (x-1,+y,+z). These interactions generate C(7) chains of molecules and R₂²(7) rings (See Fig. 2), running along [100]. Additionally, the molecules are linked by N-H···O interactions. N1-H1 acts as a hydrogen-bond donor to O2 atom of the hydroxyl group at (-x+1,-y,-z+1), forming inversion dimers (Fig. 3).

S2. Experimental

The title molecule was synthesized taking 0.100 g (0.812 mmol) of 2-amino-4-methylphenol dissolved in acetonitrile (10 mL), and then was added benzoyl chloride (0.100 mL, 0.860 mmol). The solution was placed under reflux and constant stirring for 3 hours at 150°C. The solid was filtered and recrystallized from methanol. The solvent was evaporated at room temperature and pink crystals were obtained (m.p. 448 (1)K).