2-Hy-droxy-N-(4-methyl-phen-yl)benzamide.

In the crystal structure of the title compound, C(14)H(13)NO(2), the mol-ecules 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 intra-molecular N-H⋯O and C-H⋯O hydrogen bonding, each of which completes an S(6) ring motif. The mol-ecules are stabilized in the form of supra-molecular chains extending along the crystallographic c axis due to inter-molecular 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 = 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

Δρmax = 0.19 e Å−3

Δρmin = −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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811030716/tk2771sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811030716/tk2771Isup3.cml

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

C14H13NO2	F(000) = 480
Mr = 227.25	Dx = 1.287 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1243 reflections
a = 19.4067 (17) Å	θ = 1.1–27.9°
b = 4.9122 (5) Å	µ = 0.09 mm−1
c = 12.7261 (11) Å	T = 296 K
β = 104.793 (4)°	Needle, colorless
V = 1172.96 (19) Å3	0.34 × 0.14 × 0.12 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2771 independent reflections
Radiation source: fine-focus sealed tube	1243 reflections with I > 2σ(I)
graphite	Rint = 0.060
Detector resolution: 7.6 pixels mm-1	θmax = 27.9°, θmin = 1.1°
ω scans	h = −25→25
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −4→6
Tmin = 0.979, Tmax = 0.988	l = −16→16
10416 measured reflections

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159	H-atom parameters constrained
S = 0.96	w = 1/[σ2(Fo2) + (0.0648P)2] where P = (Fo2 + 2Fc2)/3
2771 reflections	(Δ/σ)max < 0.001
156 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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
O1	0.29367 (9)	−0.2157 (4)	0.22720 (13)	0.0599 (7)
O2	0.29429 (9)	−0.0348 (3)	−0.09273 (12)	0.0598 (7)
N1	0.24804 (9)	0.0722 (4)	0.04697 (14)	0.0438 (7)
C1	0.33925 (11)	−0.2782 (5)	0.07185 (18)	0.0407 (8)
C2	0.33876 (12)	−0.3489 (5)	0.17802 (18)	0.0438 (8)
C3	0.38382 (13)	−0.5515 (5)	0.2327 (2)	0.0516 (9)
C4	0.42941 (13)	−0.6849 (5)	0.1833 (2)	0.0596 (11)
C5	0.43143 (13)	−0.6168 (6)	0.0796 (2)	0.0615 (11)
C6	0.38654 (13)	−0.4161 (5)	0.0249 (2)	0.0539 (10)
C7	0.29213 (12)	−0.0712 (5)	0.00262 (18)	0.0416 (8)
C8	0.19724 (12)	0.2725 (5)	−0.00178 (18)	0.0428 (8)
C9	0.18909 (14)	0.3743 (5)	−0.1055 (2)	0.0564 (10)
C10	0.13704 (14)	0.5697 (6)	−0.1449 (2)	0.0605 (11)
C11	0.09251 (13)	0.6670 (5)	−0.0859 (2)	0.0544 (10)
C12	0.10233 (14)	0.5654 (5)	0.0186 (2)	0.0592 (10)
C13	0.15368 (13)	0.3727 (5)	0.06023 (19)	0.0524 (9)
C14	0.03636 (15)	0.8783 (5)	−0.1313 (2)	0.0751 (11)
H1	0.29314	−0.29364	0.28396	0.0899*
H1A	0.25091	0.03812	0.11424	0.0525*
H3	0.38315	−0.59736	0.30329	0.0619*
H4	0.45896	−0.82174	0.22036	0.0714*
H5	0.46273	−0.70494	0.04648	0.0739*
H6	0.38794	−0.37165	−0.04556	0.0647*
H9	0.21810	0.31275	−0.14848	0.0677*
H10	0.13229	0.63728	−0.21461	0.0726*
H12	0.07355	0.62883	0.06158	0.0711*
H13	0.15915	0.30919	0.13074	0.0628*
H14A	0.03008	0.89281	−0.20839	0.1127*
H14B	0.05114	1.05104	−0.09782	0.1127*
H14C	−0.00787	0.82537	−0.11655	0.1127*

	U11	U22	U33	U12	U13	U23
O1	0.0753 (12)	0.0677 (13)	0.0429 (11)	0.0164 (10)	0.0262 (9)	0.0130 (9)
O2	0.0889 (13)	0.0586 (13)	0.0371 (10)	0.0035 (10)	0.0256 (9)	0.0009 (8)
N1	0.0496 (12)	0.0504 (14)	0.0318 (10)	0.0029 (10)	0.0111 (9)	0.0039 (9)
C1	0.0437 (13)	0.0379 (15)	0.0409 (14)	−0.0064 (11)	0.0117 (11)	−0.0060 (11)
C2	0.0449 (14)	0.0444 (16)	0.0438 (14)	−0.0034 (12)	0.0147 (12)	−0.0036 (12)
C3	0.0500 (14)	0.0479 (18)	0.0534 (16)	−0.0010 (13)	0.0070 (12)	0.0053 (13)
C4	0.0506 (16)	0.0481 (19)	0.077 (2)	0.0041 (13)	0.0109 (15)	0.0031 (14)
C5	0.0525 (16)	0.061 (2)	0.076 (2)	0.0033 (15)	0.0257 (15)	−0.0090 (16)
C6	0.0557 (16)	0.0571 (19)	0.0522 (16)	−0.0014 (14)	0.0197 (13)	−0.0048 (14)
C7	0.0494 (14)	0.0400 (16)	0.0365 (14)	−0.0101 (12)	0.0132 (11)	−0.0050 (11)
C8	0.0474 (14)	0.0383 (15)	0.0400 (14)	−0.0038 (12)	0.0062 (11)	0.0006 (11)
C9	0.0608 (16)	0.0616 (19)	0.0465 (16)	−0.0014 (15)	0.0130 (13)	0.0051 (14)
C10	0.0673 (18)	0.056 (2)	0.0515 (17)	−0.0024 (15)	0.0028 (14)	0.0110 (14)
C11	0.0544 (16)	0.0360 (16)	0.0628 (19)	−0.0060 (13)	−0.0031 (14)	−0.0021 (13)
C12	0.0613 (17)	0.0524 (19)	0.0615 (18)	0.0060 (14)	0.0112 (14)	−0.0038 (14)
C13	0.0599 (16)	0.0563 (18)	0.0397 (14)	0.0043 (14)	0.0105 (12)	0.0046 (12)
C14	0.0718 (19)	0.0511 (19)	0.086 (2)	0.0023 (16)	−0.0097 (16)	0.0010 (16)

O1—C2	1.366 (3)	C10—C11	1.368 (4)
O2—C7	1.238 (3)	C11—C12	1.387 (3)
O1—H1	0.8200	C11—C14	1.509 (4)
N1—C7	1.339 (3)	C12—C13	1.379 (4)
N1—C8	1.419 (3)	C3—H3	0.9300
N1—H1A	0.8600	C4—H4	0.9300
C1—C7	1.495 (3)	C5—H5	0.9300
C1—C6	1.392 (3)	C6—H6	0.9300
C1—C2	1.397 (3)	C9—H9	0.9300
C2—C3	1.389 (3)	C10—H10	0.9300
C3—C4	1.375 (4)	C12—H12	0.9300
C4—C5	1.372 (4)	C13—H13	0.9300
C5—C6	1.381 (4)	C14—H14A	0.9600
C8—C13	1.386 (3)	C14—H14B	0.9600
C8—C9	1.382 (3)	C14—H14C	0.9600
C9—C10	1.391 (4)
C2—O1—H1	109.00	C11—C12—C13	121.6 (2)
C7—N1—C8	128.90 (19)	C8—C13—C12	120.8 (2)
C8—N1—H1A	116.00	C2—C3—H3	120.00
C7—N1—H1A	116.00	C4—C3—H3	120.00
C2—C1—C6	117.5 (2)	C3—C4—H4	120.00
C2—C1—C7	125.8 (2)	C5—C4—H4	120.00
C6—C1—C7	116.7 (2)	C4—C5—H5	120.00
O1—C2—C3	120.6 (2)	C6—C5—H5	120.00
O1—C2—C1	119.2 (2)	C1—C6—H6	119.00
C1—C2—C3	120.3 (2)	C5—C6—H6	119.00
C2—C3—C4	120.6 (2)	C8—C9—H9	120.00
C3—C4—C5	120.2 (2)	C10—C9—H9	120.00
C4—C5—C6	119.3 (2)	C9—C10—H10	118.00
C1—C6—C5	122.1 (2)	C11—C10—H10	118.00
N1—C7—C1	118.03 (19)	C11—C12—H12	119.00
O2—C7—C1	120.5 (2)	C13—C12—H12	119.00
O2—C7—N1	121.5 (2)	C8—C13—H13	120.00
N1—C8—C9	124.5 (2)	C12—C13—H13	120.00
N1—C8—C13	117.0 (2)	C11—C14—H14A	109.00
C9—C8—C13	118.5 (2)	C11—C14—H14B	109.00
C8—C9—C10	119.3 (2)	C11—C14—H14C	109.00
C9—C10—C11	123.1 (2)	H14A—C14—H14B	109.00
C10—C11—C14	121.7 (2)	H14A—C14—H14C	109.00
C10—C11—C12	116.7 (2)	H14B—C14—H14C	109.00
C12—C11—C14	121.6 (2)
C8—N1—C7—O2	2.0 (4)	C1—C2—C3—C4	0.0 (4)
C8—N1—C7—C1	−178.1 (2)	C2—C3—C4—C5	0.8 (4)
C7—N1—C8—C9	−6.3 (4)	C3—C4—C5—C6	−1.0 (4)
C7—N1—C8—C13	174.3 (2)	C4—C5—C6—C1	0.4 (4)
C6—C1—C2—O1	179.2 (2)	N1—C8—C9—C10	179.6 (2)
C6—C1—C2—C3	−0.5 (4)	C13—C8—C9—C10	−1.0 (4)
C7—C1—C2—O1	−2.3 (4)	N1—C8—C13—C12	−179.2 (2)
C7—C1—C2—C3	177.9 (2)	C9—C8—C13—C12	1.4 (4)
C2—C1—C6—C5	0.3 (4)	C8—C9—C10—C11	−0.4 (4)
C7—C1—C6—C5	−178.3 (2)	C9—C10—C11—C12	1.4 (4)
C2—C1—C7—O2	−176.0 (2)	C9—C10—C11—C14	−179.7 (2)
C2—C1—C7—N1	4.1 (4)	C10—C11—C12—C13	−1.0 (4)
C6—C1—C7—O2	2.5 (3)	C14—C11—C12—C13	−179.9 (2)
C6—C1—C7—N1	−177.5 (2)	C11—C12—C13—C8	−0.4 (4)
O1—C2—C3—C4	−179.8 (2)

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

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

Symmetry code: (i) .