N-(4-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 20.02 (6)° 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 in [010].

Related literature

For biological background, see: Samanta et al. (2010 ▶). 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

Orthorhombic,

a = 7.6832 (3) Å

b = 11.0225 (3) Å

c = 27.1427 (11) Å

V = 2298.66 (14) Å3

Z = 8

Mo Kα radiation

μ = 0.32 mm−1

T = 296 K

0.28 × 0.16 × 0.14 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.942, T max = 0.955

9244 measured reflections

2064 independent reflections

1561 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.100

S = 1.03

2064 reflections

160 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.22 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 (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/S1600536810042030/hb5690sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042030/hb5690Isup2.hkl

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

C13H10ClNO2	F(000) = 1024
Mr = 247.67	Dx = 1.431 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1561 reflections
a = 7.6832 (3) Å	θ = 3.0–25.3°
b = 11.0225 (3) Å	µ = 0.32 mm−1
c = 27.1427 (11) Å	T = 296 K
V = 2298.66 (14) Å3	Needle, colorless
Z = 8	0.28 × 0.16 × 0.14 mm

Bruker Kappa APEXII CCD diffractometer	2064 independent reflections
Radiation source: fine-focus sealed tube	1561 reflections with I > 2σ(I)
graphite	Rint = 0.027
Detector resolution: 7.5 pixels mm-1	θmax = 25.3°, θmin = 3.0°
ω scans	h = −9→6
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→11
Tmin = 0.942, Tmax = 0.955	l = −24→32
9244 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0469P)2 + 0.540P] where P = (Fo2 + 2Fc2)/3
2064 reflections	(Δ/σ)max < 0.001
160 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.22 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	0.37823 (11)	0.20751 (7)	−0.03285 (2)	0.0959 (3)
O1	0.33904 (17)	−0.07407 (10)	0.19332 (4)	0.0464 (4)
O2	0.52554 (18)	0.23574 (11)	0.26024 (5)	0.0482 (5)
N1	0.3890 (2)	0.12607 (13)	0.18202 (5)	0.0423 (5)
C1	0.3726 (2)	0.04847 (14)	0.26498 (6)	0.0355 (5)
C2	0.4477 (2)	0.14916 (14)	0.28844 (6)	0.0373 (6)
C3	0.4430 (3)	0.15880 (16)	0.33940 (6)	0.0461 (6)
C4	0.3619 (3)	0.07148 (18)	0.36719 (7)	0.0519 (7)
C5	0.2852 (3)	−0.02736 (17)	0.34495 (7)	0.0513 (7)
C6	0.2926 (2)	−0.03846 (15)	0.29454 (6)	0.0421 (6)
C7	0.3672 (2)	0.02787 (15)	0.21083 (6)	0.0369 (6)
C8	0.3852 (2)	0.13776 (15)	0.13042 (6)	0.0400 (6)
C9	0.3543 (3)	0.04338 (18)	0.09804 (7)	0.0552 (7)
C10	0.3524 (3)	0.0662 (2)	0.04786 (7)	0.0622 (8)
C11	0.3811 (3)	0.1803 (2)	0.03022 (7)	0.0569 (8)
C12	0.4125 (3)	0.27414 (19)	0.06207 (8)	0.0622 (8)
C13	0.4130 (3)	0.25274 (17)	0.11203 (7)	0.0529 (7)
H1	0.413 (2)	0.1904 (18)	0.1968 (7)	0.0508*
H2	0.565 (3)	0.291 (2)	0.2768 (8)	0.0723*
H3	0.49511	0.22482	0.35481	0.0553*
H4	0.35862	0.07910	0.40130	0.0623*
H5	0.22913	−0.08592	0.36383	0.0615*
H6	0.24253	−0.10608	0.27973	0.0505*
H9	0.33497	−0.03467	0.10984	0.0663*
H10	0.33127	0.00296	0.02596	0.0746*
H12	0.43326	0.35179	0.05002	0.0747*
H13	0.43238	0.31672	0.13369	0.0635*

	U11	U22	U33	U12	U13	U23
Cl1	0.1415 (7)	0.1043 (6)	0.0418 (3)	0.0140 (4)	−0.0015 (4)	0.0171 (3)
O1	0.0660 (9)	0.0328 (7)	0.0405 (7)	0.0004 (5)	−0.0077 (6)	−0.0046 (5)
O2	0.0679 (9)	0.0339 (7)	0.0428 (8)	−0.0089 (6)	−0.0031 (6)	−0.0018 (5)
N1	0.0591 (10)	0.0321 (8)	0.0358 (8)	0.0004 (7)	−0.0009 (7)	−0.0028 (6)
C1	0.0373 (9)	0.0326 (9)	0.0366 (9)	0.0072 (7)	0.0002 (7)	−0.0006 (7)
C2	0.0416 (10)	0.0296 (9)	0.0406 (10)	0.0064 (7)	−0.0003 (8)	0.0004 (7)
C3	0.0546 (12)	0.0406 (10)	0.0431 (10)	0.0015 (9)	−0.0044 (9)	−0.0076 (8)
C4	0.0661 (13)	0.0547 (12)	0.0349 (10)	0.0049 (10)	0.0035 (9)	−0.0031 (9)
C5	0.0592 (12)	0.0490 (12)	0.0456 (11)	−0.0030 (9)	0.0109 (9)	0.0038 (8)
C6	0.0441 (11)	0.0371 (10)	0.0450 (10)	−0.0014 (8)	0.0035 (8)	−0.0034 (8)
C7	0.0370 (10)	0.0341 (10)	0.0395 (10)	0.0058 (7)	−0.0015 (7)	−0.0010 (7)
C8	0.0425 (10)	0.0412 (10)	0.0364 (10)	0.0049 (8)	−0.0015 (8)	0.0001 (7)
C9	0.0797 (15)	0.0471 (12)	0.0389 (10)	−0.0058 (10)	0.0010 (10)	−0.0005 (8)
C10	0.0862 (16)	0.0611 (14)	0.0393 (11)	−0.0050 (11)	−0.0014 (10)	−0.0059 (9)
C11	0.0687 (14)	0.0661 (14)	0.0359 (11)	0.0103 (10)	0.0010 (10)	0.0072 (9)
C12	0.0852 (16)	0.0488 (12)	0.0527 (13)	0.0050 (10)	0.0011 (11)	0.0149 (10)
C13	0.0713 (14)	0.0409 (10)	0.0466 (12)	0.0039 (9)	−0.0017 (10)	0.0018 (8)

Cl1—C11	1.738 (2)	C8—C13	1.379 (3)
O1—C7	1.239 (2)	C8—C9	1.382 (3)
O2—C2	1.362 (2)	C9—C10	1.385 (3)
O2—H2	0.82 (2)	C10—C11	1.364 (3)
N1—C8	1.407 (2)	C11—C12	1.370 (3)
N1—C7	1.346 (2)	C12—C13	1.376 (3)
N1—H1	0.84 (2)	C3—H3	0.9300
C1—C6	1.393 (2)	C4—H4	0.9300
C1—C7	1.488 (2)	C5—H5	0.9300
C1—C2	1.404 (2)	C6—H6	0.9300
C2—C3	1.388 (2)	C9—H9	0.9300
C3—C4	1.372 (3)	C10—H10	0.9300
C4—C5	1.378 (3)	C12—H12	0.9300
C5—C6	1.375 (3)	C13—H13	0.9300
C2—O2—H2	112.1 (15)	Cl1—C11—C12	119.58 (17)
C7—N1—C8	130.51 (14)	Cl1—C11—C10	120.19 (16)
C8—N1—H1	113.9 (13)	C10—C11—C12	120.23 (18)
C7—N1—H1	115.5 (13)	C11—C12—C13	119.54 (19)
C2—C1—C6	117.65 (15)	C8—C13—C12	120.92 (18)
C2—C1—C7	125.47 (14)	C2—C3—H3	120.00
C6—C1—C7	116.86 (14)	C4—C3—H3	120.00
O2—C2—C3	121.20 (15)	C3—C4—H4	120.00
O2—C2—C1	118.67 (14)	C5—C4—H4	120.00
C1—C2—C3	120.13 (15)	C4—C5—H5	120.00
C2—C3—C4	120.39 (17)	C6—C5—H5	120.00
C3—C4—C5	120.52 (17)	C1—C6—H6	119.00
C4—C5—C6	119.25 (18)	C5—C6—H6	119.00
C1—C6—C5	122.03 (16)	C8—C9—H9	120.00
N1—C7—C1	116.60 (14)	C10—C9—H9	120.00
O1—C7—C1	121.48 (14)	C9—C10—H10	120.00
O1—C7—N1	121.89 (15)	C11—C10—H10	120.00
N1—C8—C9	124.58 (16)	C11—C12—H12	120.00
N1—C8—C13	116.19 (15)	C13—C12—H12	120.00
C9—C8—C13	119.22 (16)	C8—C13—H13	120.00
C8—C9—C10	119.36 (18)	C12—C13—H13	120.00
C9—C10—C11	120.73 (19)
C8—N1—C7—O1	0.3 (3)	C1—C2—C3—C4	−1.4 (3)
C8—N1—C7—C1	−177.67 (16)	C2—C3—C4—C5	0.5 (3)
C7—N1—C8—C9	0.8 (3)	C3—C4—C5—C6	0.8 (3)
C7—N1—C8—C13	−179.92 (18)	C4—C5—C6—C1	−1.2 (3)
C6—C1—C2—O2	−179.53 (14)	N1—C8—C9—C10	179.49 (18)
C6—C1—C2—C3	0.9 (2)	C13—C8—C9—C10	0.2 (3)
C7—C1—C2—O2	−1.1 (2)	N1—C8—C13—C12	179.81 (19)
C7—C1—C2—C3	179.34 (16)	C9—C8—C13—C12	−0.8 (3)
C2—C1—C6—C5	0.4 (2)	C8—C9—C10—C11	0.2 (3)
C7—C1—C6—C5	−178.18 (16)	C9—C10—C11—Cl1	−179.98 (19)
C2—C1—C7—O1	161.80 (16)	C9—C10—C11—C12	0.1 (4)
C2—C1—C7—N1	−20.2 (2)	Cl1—C11—C12—C13	179.35 (18)
C6—C1—C7—O1	−19.8 (2)	C10—C11—C12—C13	−0.7 (4)
C6—C1—C7—N1	158.21 (15)	C11—C12—C13—C8	1.1 (3)
O2—C2—C3—C4	179.11 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.84 (2)	1.991 (18)	2.6588 (19)	136.4 (17)
O2—H2···O1i	0.82 (2)	1.85 (2)	2.6582 (17)	173 (2)
C9—H9···O1	0.93	2.31	2.895 (2)	121

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.84 (2)	1.991 (18)	2.6588 (19)	136.4 (17)
O2—H2⋯O1i	0.82 (2)	1.85 (2)	2.6582 (17)	173 (2)
C9—H9⋯O1	0.93	2.31	2.895 (2)	121

Symmetry code: (i) .