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

In the title compound, C(14)H(12)ClNO(2), the dihedral angle between the aromatic rings is 14.87 (11)° and an intra-molecular N-H⋯O hydrogen bond generates an S(6) ring. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds, generating C(6) chains propagating along the c-axis direction.

Related literature

For related structures, see: Raza et al. (2010 ▶, 2011 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H12ClNO2

M = 261.70

Monoclinic,

a = 13.8553 (12) Å

b = 7.6197 (7) Å

c = 12.0114 (11) Å

β = 104.937 (5)°

V = 1225.23 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.30 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

10366 measured reflections

2988 independent reflections

1832 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.163

S = 1.02

2988 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.21 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/S1600536812000773/hb6597sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000773/hb6597Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812000773/hb6597Isup3.cml

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

C14H12ClNO2	F(000) = 544
Mr = 261.70	Dx = 1.419 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1243 reflections
a = 13.8553 (12) Å	θ = 1.1–27.9°
b = 7.6197 (7) Å	µ = 0.30 mm−1
c = 12.0114 (11) Å	T = 296 K
β = 104.937 (5)°	Block, colorless
V = 1225.23 (19) Å3	0.34 × 0.14 × 0.12 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2988 independent reflections
Radiation source: fine-focus sealed tube	1832 reflections with I > 2σ(I)
graphite	Rint = 0.048
Detector resolution: 7.6 pixels mm-1	θmax = 28.3°, θmin = 3.0°
ω scans	h = −18→17
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −10→10
Tmin = 0.979, Tmax = 0.988	l = −15→15
10366 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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0803P)2 + 0.1504P] where P = (Fo2 + 2Fc2)/3
2988 reflections	(Δ/σ)max < 0.001
165 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.21 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 e.s.d.'s 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
Cl1	−0.34725 (5)	0.76527 (10)	−0.20816 (6)	0.0577 (3)
O1	0.02457 (12)	0.6924 (3)	−0.03254 (14)	0.0433 (6)
O2	0.00477 (12)	0.9612 (3)	0.26357 (13)	0.0429 (6)
N1	0.11035 (14)	0.8338 (3)	0.17119 (16)	0.0362 (7)
C1	−0.06586 (16)	0.8587 (3)	0.07420 (18)	0.0307 (7)
C2	−0.06343 (17)	0.7590 (3)	−0.02354 (19)	0.0309 (7)
C3	−0.15057 (17)	0.7321 (3)	−0.1100 (2)	0.0369 (8)
C4	−0.23926 (18)	0.8024 (3)	−0.1004 (2)	0.0395 (8)
C5	−0.24347 (18)	0.9064 (4)	−0.0066 (2)	0.0433 (9)
C6	−0.15738 (17)	0.9312 (3)	0.0788 (2)	0.0378 (8)
C7	0.01973 (17)	0.8882 (3)	0.17747 (19)	0.0330 (7)
C8	0.20016 (17)	0.8321 (3)	0.25990 (19)	0.0336 (7)
C9	0.21756 (18)	0.9335 (3)	0.3585 (2)	0.0398 (8)
C10	0.30691 (19)	0.9134 (4)	0.4426 (2)	0.0442 (9)
C11	0.38017 (19)	0.7971 (4)	0.4309 (2)	0.0447 (9)
C12	0.36287 (19)	0.7055 (4)	0.3288 (2)	0.0498 (9)
C13	0.27424 (19)	0.7211 (3)	0.2442 (2)	0.0440 (8)
C14	0.4741 (2)	0.7698 (4)	0.5263 (3)	0.0643 (11)
H1	0.11427	0.79538	0.10518	0.0435*
H1A	0.01808	0.65337	−0.09769	0.0649*
H3	−0.14878	0.66625	−0.17466	0.0443*
H5	−0.30317	0.95784	−0.00191	0.0519*
H6	−0.16000	0.99904	0.14229	0.0454*
H9	0.17007	1.01407	0.36852	0.0478*
H10	0.31781	0.98082	0.50924	0.0531*
H12	0.41224	0.63092	0.31648	0.0598*
H13	0.26452	0.65658	0.17647	0.0528*
H14A	0.52971	0.75280	0.49345	0.0964*
H14B	0.46641	0.66814	0.57041	0.0964*
H14C	0.48596	0.87099	0.57550	0.0964*

	U11	U22	U33	U12	U13	U23
Cl1	0.0388 (4)	0.0747 (6)	0.0499 (4)	−0.0043 (3)	−0.0061 (3)	−0.0010 (4)
O1	0.0351 (9)	0.0606 (12)	0.0338 (10)	0.0033 (8)	0.0084 (7)	−0.0120 (9)
O2	0.0414 (10)	0.0602 (12)	0.0272 (9)	0.0023 (9)	0.0092 (7)	−0.0060 (8)
N1	0.0368 (11)	0.0452 (13)	0.0260 (10)	−0.0010 (9)	0.0068 (8)	−0.0022 (9)
C1	0.0343 (12)	0.0321 (13)	0.0252 (12)	−0.0021 (10)	0.0070 (9)	0.0041 (10)
C2	0.0314 (12)	0.0324 (13)	0.0294 (12)	−0.0004 (9)	0.0089 (9)	0.0042 (10)
C3	0.0388 (13)	0.0418 (15)	0.0294 (13)	−0.0043 (11)	0.0078 (10)	−0.0026 (10)
C4	0.0348 (13)	0.0446 (15)	0.0358 (14)	−0.0041 (11)	0.0034 (10)	0.0053 (11)
C5	0.0346 (14)	0.0503 (17)	0.0444 (15)	0.0045 (11)	0.0093 (11)	0.0018 (12)
C6	0.0395 (13)	0.0400 (14)	0.0341 (13)	0.0025 (11)	0.0098 (10)	−0.0020 (11)
C7	0.0386 (13)	0.0331 (13)	0.0284 (12)	−0.0039 (10)	0.0108 (10)	0.0054 (10)
C8	0.0352 (12)	0.0374 (14)	0.0276 (12)	−0.0045 (10)	0.0071 (10)	0.0026 (10)
C9	0.0386 (14)	0.0428 (15)	0.0374 (14)	−0.0022 (11)	0.0088 (11)	−0.0047 (11)
C10	0.0453 (15)	0.0510 (17)	0.0338 (14)	−0.0094 (12)	0.0056 (11)	−0.0053 (12)
C11	0.0385 (14)	0.0516 (16)	0.0394 (15)	−0.0056 (12)	0.0017 (11)	0.0051 (12)
C12	0.0364 (14)	0.0592 (18)	0.0513 (17)	0.0051 (12)	0.0066 (12)	−0.0047 (14)
C13	0.0418 (14)	0.0518 (16)	0.0381 (14)	−0.0005 (12)	0.0098 (11)	−0.0089 (12)
C14	0.0489 (18)	0.074 (2)	0.057 (2)	−0.0018 (15)	−0.0098 (14)	0.0058 (16)

Cl1—C4	1.731 (3)	C9—C10	1.390 (4)
O1—C2	1.351 (3)	C10—C11	1.382 (4)
O2—C7	1.238 (3)	C11—C12	1.377 (4)
O1—H1A	0.8200	C11—C14	1.510 (4)
N1—C7	1.343 (3)	C12—C13	1.383 (4)
N1—C8	1.414 (3)	C3—H3	0.9300
N1—H1	0.8600	C5—H5	0.9300
C1—C7	1.496 (3)	C6—H6	0.9300
C1—C6	1.397 (3)	C9—H9	0.9300
C1—C2	1.406 (3)	C10—H10	0.9300
C2—C3	1.390 (3)	C12—H12	0.9300
C3—C4	1.372 (3)	C13—H13	0.9300
C4—C5	1.391 (3)	C14—H14A	0.9600
C5—C6	1.371 (3)	C14—H14B	0.9600
C8—C13	1.380 (3)	C14—H14C	0.9600
C8—C9	1.382 (3)
C2—O1—H1A	109.00	C10—C11—C12	116.9 (2)
C7—N1—C8	127.9 (2)	C12—C11—C14	121.6 (3)
C7—N1—H1	116.00	C11—C12—C13	121.9 (3)
C8—N1—H1	116.00	C8—C13—C12	120.2 (2)
C2—C1—C6	117.6 (2)	C2—C3—H3	120.00
C2—C1—C7	126.1 (2)	C4—C3—H3	120.00
C6—C1—C7	116.2 (2)	C4—C5—H5	121.00
C1—C2—C3	120.0 (2)	C6—C5—H5	121.00
O1—C2—C1	119.1 (2)	C1—C6—H6	119.00
O1—C2—C3	120.9 (2)	C5—C6—H6	119.00
C2—C3—C4	120.3 (2)	C8—C9—H9	120.00
Cl1—C4—C3	119.57 (18)	C10—C9—H9	120.00
Cl1—C4—C5	119.4 (2)	C9—C10—H10	119.00
C3—C4—C5	121.1 (2)	C11—C10—H10	119.00
C4—C5—C6	118.3 (2)	C11—C12—H12	119.00
C1—C6—C5	122.6 (2)	C13—C12—H12	119.00
N1—C7—C1	117.4 (2)	C8—C13—H13	120.00
O2—C7—C1	119.5 (2)	C12—C13—H13	120.00
O2—C7—N1	123.1 (2)	C11—C14—H14A	109.00
N1—C8—C9	124.5 (2)	C11—C14—H14B	109.00
N1—C8—C13	116.3 (2)	C11—C14—H14C	110.00
C9—C8—C13	119.2 (2)	H14A—C14—H14B	109.00
C8—C9—C10	119.2 (2)	H14A—C14—H14C	109.00
C9—C10—C11	122.5 (2)	H14B—C14—H14C	110.00
C10—C11—C14	121.5 (2)
C8—N1—C7—O2	6.7 (4)	C2—C3—C4—Cl1	−179.23 (18)
C8—N1—C7—C1	−173.7 (2)	C2—C3—C4—C5	2.2 (4)
C7—N1—C8—C9	−20.6 (4)	Cl1—C4—C5—C6	178.8 (2)
C7—N1—C8—C13	159.8 (2)	C3—C4—C5—C6	−2.7 (4)
C6—C1—C2—O1	177.7 (2)	C4—C5—C6—C1	1.1 (4)
C6—C1—C2—C3	−1.5 (3)	N1—C8—C9—C10	176.5 (2)
C7—C1—C2—O1	−5.5 (4)	C13—C8—C9—C10	−3.9 (4)
C7—C1—C2—C3	175.4 (2)	N1—C8—C13—C12	−177.2 (2)
C2—C1—C6—C5	1.0 (4)	C9—C8—C13—C12	3.1 (4)
C7—C1—C6—C5	−176.2 (2)	C8—C9—C10—C11	0.9 (4)
C2—C1—C7—O2	−171.4 (2)	C9—C10—C11—C12	2.7 (4)
C2—C1—C7—N1	8.9 (3)	C9—C10—C11—C14	−176.4 (3)
C6—C1—C7—O2	5.5 (3)	C10—C11—C12—C13	−3.5 (4)
C6—C1—C7—N1	−174.1 (2)	C14—C11—C12—C13	175.6 (3)
O1—C2—C3—C4	−179.2 (2)	C11—C12—C13—C8	0.7 (4)
C1—C2—C3—C4	−0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	1.96	2.658 (3)	138
O1—H1A···O2i	0.82	1.85	2.664 (2)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86	1.96	2.658 (3)	138
O1—H1A⋯O2i	0.82	1.85	2.664 (2)	173

Symmetry code: (i) .