Crystal structure of N-(2-hy-droxy-5-methyl-phen-yl)benzamide.

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 hy-droxy-phenyl rings, respectively. A short intra-molecular N-H⋯O contact is present. In the crystal, the mol-ecules 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 inter-actions link the mol-ecules into inversion dimers.

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 = 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

Δρmax = 0.33 e Å−3

Δρmin = −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 ▸).

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

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

Click here for additional data file.

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

Click here for additional data file.

. 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.

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.

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

C14H13NO2	Dx = 1.370 Mg m−3
Mr = 227.25	Melting point: 448(1) K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.2263 (3) Å	Cell parameters from 10254 reflections
b = 21.7442 (7) Å	θ = 3.4–29.4°
c = 7.4747 (3) Å	µ = 0.09 mm−1
β = 110.280 (5)°	T = 123 K
V = 1101.69 (8) Å3	Block, pink
Z = 4	0.40 × 0.35 × 0.25 mm
F(000) = 480

Oxford Diffraction Gemini S CCD diffractometer	2332 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
Graphite monochromator	θmax = 29.4°, θmin = 3.4°
ω scans	h = −9→9
10254 measured reflections	k = −30→30
2795 independent reflections	l = −9→10

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043	Hydrogen site location: mixed
wR(F2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0448P)2 + 0.5141P] where P = (Fo2 + 2Fc2)/3
2795 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Experimental. The IR spectrum was recorded on a FT—IR SHIMADZU IR-Affinity-1 spectrophotometer. IR (KBr), cm-1, 3395 (amide N-H); 3073 (Hydroxyl O-H), 1643 (amide, C=O); 1593 (C=C).

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O2	0.55117 (13)	0.05937 (4)	0.41236 (14)	0.0204 (2)
O1	−0.14306 (13)	0.07692 (4)	0.30232 (14)	0.0214 (2)
N1	0.17579 (15)	0.05132 (5)	0.36397 (15)	0.0166 (2)
C1	−0.07846 (17)	−0.02289 (5)	0.20522 (16)	0.0153 (2)
C2	0.05257 (19)	−0.06486 (6)	0.17363 (18)	0.0192 (3)
H2	0.1892	−0.0554	0.2136	0.023*
C3	−0.0159 (2)	−0.12053 (6)	0.08386 (19)	0.0222 (3)
H3	0.0743	−0.1490	0.0632	0.027*
C4	−0.2145 (2)	−0.13469 (6)	0.02438 (18)	0.0217 (3)
H4	−0.2607	−0.1728	−0.0371	0.026*
C5	−0.34605 (19)	−0.09320 (6)	0.05467 (19)	0.0224 (3)
H5	−0.4827	−0.1028	0.0136	0.027*
C6	−0.27845 (18)	−0.03785 (6)	0.14471 (18)	0.0193 (3)
H6	−0.3693	−0.0097	0.1656	0.023*
C7	−0.01844 (17)	0.03897 (5)	0.29485 (17)	0.0150 (2)
C8	0.26922 (17)	0.10733 (5)	0.43855 (17)	0.0149 (2)
C13	0.17867 (18)	0.15716 (6)	0.48997 (17)	0.0172 (3)
H13	0.0430	0.1547	0.4756	0.021*
C12	0.28408 (19)	0.21075 (6)	0.56243 (18)	0.0186 (3)
C11	0.48182 (19)	0.21370 (6)	0.58174 (18)	0.0202 (3)
H11	0.5548	0.2501	0.6301	0.024*
C10	0.57479 (18)	0.16395 (6)	0.53108 (18)	0.0195 (3)
H10	0.7104	0.1666	0.5452	0.023*
C9	0.46985 (17)	0.11075 (5)	0.46028 (17)	0.0157 (2)
C14	0.1817 (2)	0.26392 (6)	0.6182 (2)	0.0258 (3)
H141	0.2788	0.2956	0.6812	0.039*
H142	0.1168	0.2495	0.7059	0.039*
H143	0.0827	0.2813	0.5038	0.039*
H1	0.258 (2)	0.0217 (8)	0.357 (2)	0.031 (4)*
H20	0.658 (3)	0.0685 (9)	0.383 (3)	0.047 (6)*

	U11	U22	U33	U12	U13	U23
O2	0.0158 (4)	0.0173 (4)	0.0316 (5)	0.0009 (3)	0.0126 (4)	−0.0013 (4)
O1	0.0150 (4)	0.0177 (4)	0.0333 (5)	0.0005 (3)	0.0108 (4)	−0.0022 (4)
N1	0.0129 (5)	0.0147 (5)	0.0224 (5)	0.0010 (4)	0.0063 (4)	−0.0027 (4)
C1	0.0170 (6)	0.0148 (5)	0.0142 (5)	−0.0004 (4)	0.0056 (4)	0.0008 (4)
C2	0.0161 (6)	0.0200 (6)	0.0210 (6)	0.0009 (5)	0.0056 (5)	−0.0008 (5)
C3	0.0235 (7)	0.0188 (6)	0.0240 (6)	0.0027 (5)	0.0078 (5)	−0.0030 (5)
C4	0.0267 (7)	0.0172 (6)	0.0190 (6)	−0.0028 (5)	0.0051 (5)	−0.0012 (5)
C5	0.0186 (6)	0.0230 (6)	0.0238 (6)	−0.0047 (5)	0.0051 (5)	−0.0013 (5)
C6	0.0162 (6)	0.0197 (6)	0.0220 (6)	0.0008 (5)	0.0065 (5)	−0.0002 (5)
C7	0.0143 (5)	0.0156 (6)	0.0164 (5)	0.0010 (4)	0.0069 (4)	0.0014 (4)
C8	0.0145 (6)	0.0150 (5)	0.0146 (5)	−0.0003 (4)	0.0043 (4)	0.0009 (4)
C13	0.0161 (6)	0.0180 (6)	0.0180 (6)	0.0012 (4)	0.0065 (5)	−0.0001 (4)
C12	0.0227 (6)	0.0155 (6)	0.0178 (6)	0.0015 (5)	0.0073 (5)	0.0006 (4)
C11	0.0230 (7)	0.0149 (6)	0.0222 (6)	−0.0034 (5)	0.0071 (5)	0.0006 (5)
C10	0.0152 (6)	0.0195 (6)	0.0238 (6)	−0.0019 (5)	0.0069 (5)	0.0027 (5)
C9	0.0153 (6)	0.0156 (5)	0.0172 (6)	0.0022 (4)	0.0070 (5)	0.0022 (4)
C14	0.0297 (7)	0.0184 (6)	0.0308 (7)	0.0023 (5)	0.0125 (6)	−0.0044 (5)

O2—C9	1.3667 (14)	C5—H5	0.9500
O2—H20	0.89 (2)	C6—H6	0.9500
O1—C7	1.2369 (14)	C8—C13	1.3871 (16)
N1—C7	1.3440 (15)	C8—C9	1.4038 (16)
N1—C8	1.4103 (15)	C13—C12	1.3949 (17)
N1—H1	0.889 (18)	C13—H13	0.9500
C1—C2	1.3929 (17)	C12—C11	1.3870 (18)
C1—C6	1.3949 (17)	C12—C14	1.5074 (17)
C1—C7	1.4984 (16)	C11—C10	1.3933 (18)
C2—C3	1.3893 (17)	C11—H11	0.9500
C2—H2	0.9500	C10—C9	1.3838 (17)
C3—C4	1.3818 (19)	C10—H10	0.9500
C3—H3	0.9500	C14—H141	0.9800
C4—C5	1.3849 (19)	C14—H142	0.9800
C4—H4	0.9500	C14—H143	0.9800
C5—C6	1.3829 (18)
C9—O2—H20	111.6 (12)	C13—C8—C9	119.61 (11)
C7—N1—C8	128.14 (10)	C13—C8—N1	125.23 (11)
C7—N1—H1	117.3 (11)	C9—C8—N1	115.16 (10)
C8—N1—H1	114.4 (11)	C8—C13—C12	120.90 (11)
C2—C1—C6	118.75 (11)	C8—C13—H13	119.5
C2—C1—C7	123.75 (11)	C12—C13—H13	119.5
C6—C1—C7	117.46 (10)	C11—C12—C13	118.90 (11)
C3—C2—C1	120.22 (12)	C11—C12—C14	121.51 (12)
C3—C2—H2	119.9	C13—C12—C14	119.59 (11)
C1—C2—H2	119.9	C12—C11—C10	120.82 (11)
C4—C3—C2	120.39 (12)	C12—C11—H11	119.6
C4—C3—H3	119.8	C10—C11—H11	119.6
C2—C3—H3	119.8	C9—C10—C11	120.07 (11)
C3—C4—C5	119.83 (12)	C9—C10—H10	120.0
C3—C4—H4	120.1	C11—C10—H10	120.0
C5—C4—H4	120.1	O2—C9—C10	123.73 (11)
C6—C5—C4	119.99 (12)	O2—C9—C8	116.55 (10)
C6—C5—H5	120.0	C10—C9—C8	119.71 (11)
C4—C5—H5	120.0	C12—C14—H141	109.5
C5—C6—C1	120.81 (12)	C12—C14—H142	109.5
C5—C6—H6	119.6	H141—C14—H142	109.5
C1—C6—H6	119.6	C12—C14—H143	109.5
O1—C7—N1	121.94 (11)	H141—C14—H143	109.5
O1—C7—C1	121.11 (11)	H142—C14—H143	109.5
N1—C7—C1	116.95 (10)
C6—C1—C2—C3	−0.16 (18)	C7—N1—C8—C9	−166.27 (11)
C7—C1—C2—C3	−177.86 (11)	C9—C8—C13—C12	0.22 (18)
C1—C2—C3—C4	0.27 (19)	N1—C8—C13—C12	−179.91 (11)
C2—C3—C4—C5	−0.10 (19)	C8—C13—C12—C11	0.28 (18)
C3—C4—C5—C6	−0.2 (2)	C8—C13—C12—C14	−179.59 (12)
C4—C5—C6—C1	0.3 (2)	C13—C12—C11—C10	−0.44 (19)
C2—C1—C6—C5	−0.12 (18)	C14—C12—C11—C10	179.44 (12)
C7—C1—C6—C5	177.72 (11)	C12—C11—C10—C9	0.08 (19)
C8—N1—C7—O1	−5.48 (19)	C11—C10—C9—O2	−178.11 (11)
C8—N1—C7—C1	173.71 (10)	C11—C10—C9—C8	0.44 (18)
C2—C1—C7—O1	172.66 (12)	C13—C8—C9—O2	178.06 (11)
C6—C1—C7—O1	−5.06 (17)	N1—C8—C9—O2	−1.82 (15)
C2—C1—C7—N1	−6.54 (17)	C13—C8—C9—C10	−0.59 (17)
C6—C1—C7—N1	175.74 (11)	N1—C8—C9—C10	179.54 (11)
C7—N1—C8—C13	13.9 (2)

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

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

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