N-(3-Chloro-phen-yl)-2-hy-droxy-benzamide.

In the title compound, C(13)H(10)ClNO(2), the dihedral angle between the aromatic rings is 5.57 (9)° and intra-molecular N-H⋯O and C-H⋯O hydrogen bonds both generate S(6) rings. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds into C(6) chains propagating along [010]. Mol-ecules from neighbouring chains along the z axis are involved in C-H⋯π and π-π stacking inter-actions [centroid-centroid distance = 3.9340 (10) Å].

Related literature

For pharmacological background to this work, see: Coupet et al. (1979 ▶); Pae et al. (2004 ▶). For related structures, see: Raza et al. (2009 ▶, 2010a ▶,b ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H10ClNO2

M = 247.67

Monoclinic,

a = 13.4638 (5) Å

b = 11.9019 (4) Å

c = 7.1764 (2) Å

β = 98.808 (2)°

V = 1136.42 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 296 K

0.24 × 0.16 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.982, T max = 0.987

10332 measured reflections

2806 independent reflections

1827 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.115

S = 1.03

2806 reflections

161 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.34 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 datablocks global, I. DOI: 10.1107/S1600536810045046/gk2313sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045046/gk2313Isup2.hkl

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

C13H10ClNO2	F(000) = 512
Mr = 247.67	Dx = 1.448 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1827 reflections
a = 13.4638 (5) Å	θ = 1.5–28.5°
b = 11.9019 (4) Å	µ = 0.32 mm−1
c = 7.1764 (2) Å	T = 296 K
β = 98.808 (2)°	Prism, white
V = 1136.42 (7) Å3	0.24 × 0.16 × 0.15 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2806 independent reflections
Radiation source: fine-focus sealed tube	1827 reflections with I > 2σ(I)
graphite	Rint = 0.033
Detector resolution: 7.5 pixels mm-1	θmax = 28.5°, θmin = 2.3°
ω scans	h = −17→17
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −15→15
Tmin = 0.982, Tmax = 0.987	l = −5→9
10332 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0498P)2 + 0.1662P] where P = (Fo2 + 2Fc2)/3
2806 reflections	(Δ/σ)max = 0.001
161 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.34 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	0.95784 (4)	−0.09691 (5)	0.80925 (10)	0.0858 (3)
O1	0.49322 (9)	−0.04858 (10)	0.79519 (19)	0.0502 (3)
H1	0.4719 (16)	−0.1099 (18)	0.840 (3)	0.071 (7)*
O2	0.55912 (9)	0.26044 (9)	0.57224 (17)	0.0480 (3)
N1	0.61841 (11)	0.09050 (11)	0.6738 (2)	0.0414 (3)
H1A	0.5995 (13)	0.0264 (16)	0.714 (2)	0.050*
C1	0.44202 (12)	0.13109 (13)	0.6707 (2)	0.0365 (4)
C2	0.41952 (12)	0.02934 (13)	0.7532 (2)	0.0389 (4)
C3	0.32279 (13)	0.00851 (15)	0.7912 (2)	0.0461 (4)
H3	0.3090	−0.0579	0.8505	0.055*
C4	0.24770 (14)	0.08575 (16)	0.7414 (3)	0.0522 (5)
H4	0.1834	0.0714	0.7677	0.063*
C5	0.26700 (13)	0.18469 (15)	0.6526 (3)	0.0536 (5)
H5	0.2155	0.2358	0.6160	0.064*
C6	0.36320 (13)	0.20707 (14)	0.6187 (2)	0.0452 (4)
H6	0.3760	0.2741	0.5600	0.054*
C7	0.54346 (12)	0.16594 (13)	0.6345 (2)	0.0367 (4)
C8	0.72051 (13)	0.10029 (13)	0.6548 (2)	0.0390 (4)
C9	0.78234 (13)	0.01425 (15)	0.7347 (2)	0.0456 (4)
H9	0.7562	−0.0433	0.8002	0.055*
C10	0.88287 (14)	0.01472 (16)	0.7165 (3)	0.0522 (5)
C11	0.92390 (15)	0.09982 (18)	0.6235 (3)	0.0589 (5)
H11	0.9920	0.1001	0.6141	0.071*
C12	0.86155 (14)	0.18490 (16)	0.5443 (3)	0.0547 (5)
H12	0.8883	0.2427	0.4802	0.066*
C13	0.76052 (13)	0.18621 (14)	0.5579 (2)	0.0467 (4)
H13	0.7196	0.2439	0.5030	0.056*

	U11	U22	U33	U12	U13	U23
Cl1	0.0602 (4)	0.0860 (5)	0.1122 (5)	0.0296 (3)	0.0165 (3)	0.0241 (4)
O1	0.0486 (7)	0.0319 (7)	0.0723 (9)	0.0043 (6)	0.0163 (6)	0.0114 (6)
O2	0.0565 (8)	0.0283 (6)	0.0615 (8)	0.0036 (5)	0.0166 (6)	0.0055 (5)
N1	0.0423 (8)	0.0303 (7)	0.0532 (9)	0.0016 (6)	0.0123 (6)	0.0043 (6)
C1	0.0434 (9)	0.0304 (8)	0.0350 (8)	0.0017 (7)	0.0033 (7)	−0.0061 (6)
C2	0.0437 (9)	0.0322 (8)	0.0402 (9)	0.0015 (7)	0.0044 (7)	−0.0051 (7)
C3	0.0465 (10)	0.0411 (10)	0.0506 (10)	−0.0058 (8)	0.0076 (8)	−0.0008 (8)
C4	0.0391 (10)	0.0557 (12)	0.0611 (11)	−0.0035 (8)	0.0056 (8)	−0.0098 (9)
C5	0.0431 (10)	0.0474 (11)	0.0666 (12)	0.0093 (8)	−0.0040 (9)	−0.0048 (9)
C6	0.0463 (10)	0.0362 (9)	0.0507 (10)	0.0044 (8)	−0.0010 (8)	−0.0024 (7)
C7	0.0456 (9)	0.0273 (8)	0.0370 (8)	0.0027 (7)	0.0062 (7)	−0.0049 (6)
C8	0.0426 (9)	0.0351 (9)	0.0404 (9)	0.0006 (7)	0.0095 (7)	−0.0055 (7)
C9	0.0472 (10)	0.0415 (10)	0.0495 (10)	0.0040 (8)	0.0122 (8)	0.0022 (8)
C10	0.0467 (10)	0.0532 (11)	0.0563 (11)	0.0094 (9)	0.0065 (8)	−0.0018 (9)
C11	0.0426 (10)	0.0674 (13)	0.0679 (13)	−0.0031 (10)	0.0125 (9)	−0.0082 (10)
C12	0.0542 (11)	0.0509 (11)	0.0617 (12)	−0.0099 (9)	0.0174 (9)	−0.0004 (9)
C13	0.0507 (10)	0.0394 (10)	0.0508 (10)	−0.0028 (8)	0.0105 (8)	0.0000 (8)

Cl1—C10	1.7381 (19)	C4—H4	0.9300
O1—C2	1.3579 (19)	C5—C6	1.380 (2)
O1—H1	0.87 (2)	C5—H5	0.9300
O2—C7	1.2400 (19)	C6—H6	0.9300
N1—C7	1.348 (2)	C8—C9	1.387 (2)
N1—C8	1.407 (2)	C8—C13	1.391 (2)
N1—H1A	0.866 (18)	C9—C10	1.380 (2)
C1—C6	1.401 (2)	C9—H9	0.9300
C1—C2	1.401 (2)	C10—C11	1.375 (3)
C1—C7	1.488 (2)	C11—C12	1.381 (3)
C2—C3	1.393 (2)	C11—H11	0.9300
C3—C4	1.373 (2)	C12—C13	1.379 (2)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.383 (3)	C13—H13	0.9300
C2—O1—H1	112.7 (14)	O2—C7—N1	121.10 (15)
C7—N1—C8	129.47 (14)	O2—C7—C1	121.81 (14)
C7—N1—H1A	114.0 (12)	N1—C7—C1	117.09 (14)
C8—N1—H1A	116.5 (12)	C9—C8—C13	119.72 (16)
C6—C1—C2	117.81 (15)	C9—C8—N1	115.60 (14)
C6—C1—C7	116.86 (14)	C13—C8—N1	124.65 (15)
C2—C1—C7	125.34 (14)	C10—C9—C8	119.55 (17)
O1—C2—C3	120.55 (15)	C10—C9—H9	120.2
O1—C2—C1	119.08 (15)	C8—C9—H9	120.2
C3—C2—C1	120.37 (15)	C11—C10—C9	121.47 (18)
C4—C3—C2	120.22 (16)	C11—C10—Cl1	119.74 (15)
C4—C3—H3	119.9	C9—C10—Cl1	118.78 (15)
C2—C3—H3	119.9	C10—C11—C12	118.42 (18)
C3—C4—C5	120.50 (17)	C10—C11—H11	120.8
C3—C4—H4	119.7	C12—C11—H11	120.8
C5—C4—H4	119.7	C13—C12—C11	121.54 (18)
C6—C5—C4	119.56 (17)	C13—C12—H12	119.2
C6—C5—H5	120.2	C11—C12—H12	119.2
C4—C5—H5	120.2	C12—C13—C8	119.29 (17)
C5—C6—C1	121.45 (16)	C12—C13—H13	120.4
C5—C6—H6	119.3	C8—C13—H13	120.4
C1—C6—H6	119.3
C8—N1—C7—O2	−0.4 (3)	C1—C2—C3—C4	2.6 (3)
C8—N1—C7—C1	−179.66 (16)	C2—C3—C4—C5	0.2 (3)
C7—N1—C8—C9	170.31 (17)	C3—C4—C5—C6	−1.8 (3)
C7—N1—C8—C13	−11.9 (3)	C4—C5—C6—C1	0.7 (3)
C6—C1—C2—O1	176.28 (15)	N1—C8—C9—C10	177.43 (18)
C6—C1—C2—C3	−3.6 (2)	C13—C8—C9—C10	−0.4 (3)
C7—C1—C2—O1	−4.1 (2)	N1—C8—C13—C12	−178.15 (19)
C7—C1—C2—C3	176.04 (16)	C9—C8—C13—C12	−0.5 (3)
C2—C1—C6—C5	2.0 (3)	C8—C9—C10—Cl1	−177.25 (16)
C7—C1—C6—C5	−177.67 (17)	C8—C9—C10—C11	1.4 (3)
C2—C1—C7—O2	−175.16 (15)	Cl1—C10—C11—C12	177.29 (17)
C2—C1—C7—N1	4.1 (2)	C9—C10—C11—C12	−1.3 (3)
C6—C1—C7—O2	4.5 (2)	C10—C11—C12—C13	0.4 (3)
C6—C1—C7—N1	−176.25 (15)	C11—C12—C13—C8	0.5 (3)
O1—C2—C3—C4	−177.32 (17)

Cg1 is the centroid of the C1–C6 benzene ring

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.88 (2)	1.73 (2)	2.6016 (18)	173 (2)
N1—H1A···O1	0.88 (2)	1.85 (2)	2.606 (2)	143.4 (18)
C13—H13···O2	0.93	2.30	2.869 (2)	119
C6—H6···Cg1ii	0.93	2.89	3.675 (2)	143

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.88 (2)	1.73 (2)	2.6016 (18)	173 (2)
N1—H1A⋯O1	0.88 (2)	1.85 (2)	2.606 (2)	143.4 (18)
C13—H13⋯O2	0.93	2.30	2.869 (2)	119
C6—H6⋯Cg1ii	0.93	2.89	3.675 (2)	143

Symmetry codes: (i) ; (ii) .