Crystal structure of 4-bromo-N-(2-hydroxy-phen-yl)benzamide.

In the title compound, C13H10BrNO2, the mean plane of the non-H atoms of the central amide C-N-C(=O)-C fragment (r.m.s. deviation = 0.004 Å) forms a dihedral angle of 73.97 (12)° with the hy-droxy-substituted benzene ring and 25.42 (19)° with the bromo-substituted benzene ring. The two aromatic rings are inclined to one another by 80.7 (2)°. In the crystal, mol-ecules are linked by O-H⋯O and N-H⋯O hydrogen bonds, forming chains along [010]. The chains are linked by weak C-H⋯O hydrogen bonds, forming sheets parallel to (100), and enclosing R (3) 3(17) and R (3) 2(9) ring motifs.

Related literature

For the anti­protozoal and anti­microbial properties of phenyl­benzamides, see: Ríos Martínez et al. (2014 ▶); Şener et al. (2000 ▶). For active metabolites of benzoxazoles, see: Mobinikhaledi et al. (2006 ▶). For studies of phenyl­benzamides as inhibitors of tyrosine kinases, see: Capdeville et al. (2002 ▶). For studies of phenyl­benzamides as inducers of apoptosis in biological processes, see: Olsson et al. (2002 ▶). For related structures, see: Fun et al. (2012 ▶); Hibbert et al. (1998 ▶).

Experimental

Crystal data

C13H10BrNO2

M = 292.13

Monoclinic,

a = 23.4258 (10) Å

b = 5.6473 (1) Å

c = 9.2464 (3) Å

β = 93.008 (1)°

V = 1221.54 (7) Å3

Z = 4

Mo Kα radiation

μ = 3.35 mm−1

T = 295 K

0.20 × 0.18 × 0.13 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.537, T max = 0.662

21458 measured reflections

2490 independent reflections

1664 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.168

S = 0.99

2490 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.61 e Å−3

Δρmin = −0.68 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; 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, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814024696/su5019sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814024696/su5019Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814024696/su5019Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814024696/su5019fig1.tif

The mol­ecular structure of the title compound (I), with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.

a 3 3 3 2 . DOI: 10.1107/S1600536814024696/su5019fig2.tif

Part of the crystal packing of the title compound (I) viewed along the a axis, showing the formation of R3 3(17) and R3 2(9) ring motifs within the two-dimensional hydrogen bonded network running parallel to (100). Hydrogen bonds are shown as dashed lines; see Table 1 for details [symmetry codes: (i) x, −y-3/2, z-1/2; (ii) x, −y-1/2, z-1/2; (iii) x, y+1, z].

CCDC reference: 1033535

Additional supporting information: crystallographic information; 3D view; checkCIF report

C13H10BrNO2	F(000) = 584
Mr = 292.13	Dx = 1.588 Mg m−3
Monoclinic, P21/c	Melting point: 454(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 23.4258 (10) Å	Cell parameters from 2490 reflections
b = 5.6473 (1) Å	θ = 3.5–26.4°
c = 9.2464 (3) Å	µ = 3.35 mm−1
β = 93.008 (1)°	T = 295 K
V = 1221.54 (7) Å3	Block, black
Z = 4	0.20 × 0.18 × 0.13 mm

Nonius KappaCCD diffractometer	2490 independent reflections
Radiation source: fine-focus sealed tube	1664 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.063
CCD rotation images, thick slices scans	θmax = 26.4°, θmin = 3.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −29→29
Tmin = 0.537, Tmax = 0.662	k = −7→6
21458 measured reflections	l = −11→11

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0999P)2 + 0.5651P] where P = (Fo2 + 2Fc2)/3
2490 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.61 e Å−3
0 restraints	Δρmin = −0.68 e Å−3

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
Br1	0.46192 (2)	1.31657 (9)	0.85256 (8)	0.1081 (3)
O1	0.23094 (11)	0.5820 (4)	0.8853 (2)	0.0546 (6)
C7	0.24418 (16)	0.7116 (6)	0.7843 (3)	0.0462 (8)
C9	0.15972 (16)	0.4064 (6)	0.5411 (4)	0.0513 (8)
O2	0.20914 (13)	0.3579 (5)	0.4767 (3)	0.0700 (8)
HO2	0.2040	0.2472	0.4201	0.105*
N1	0.21228 (13)	0.7256 (5)	0.6607 (3)	0.0520 (7)
H1	0.2235	0.8168	0.5933	0.062*
C1	0.29740 (16)	0.8587 (6)	0.7961 (3)	0.0490 (8)
C6	0.30259 (17)	1.0664 (6)	0.7177 (4)	0.0565 (9)
H6	0.2728	1.1161	0.6543	0.068*
C8	0.16058 (15)	0.5964 (6)	0.6357 (3)	0.0500 (8)
C5	0.3522 (2)	1.1998 (7)	0.7340 (5)	0.0675 (11)
H5	0.3560	1.3385	0.6811	0.081*
C2	0.34181 (18)	0.7886 (7)	0.8900 (4)	0.0604 (9)
H2	0.3384	0.6499	0.9431	0.073*
C4	0.39549 (18)	1.1262 (7)	0.8281 (5)	0.0665 (10)
C13	0.1110 (2)	0.6596 (7)	0.7011 (4)	0.0683 (11)
H13	0.1113	0.7876	0.7645	0.082*
C10	0.11003 (19)	0.2786 (8)	0.5152 (5)	0.0696 (11)
H10	0.1096	0.1490	0.4532	0.083*
C11	0.0610 (2)	0.3429 (9)	0.5812 (5)	0.0816 (13)
H11	0.0275	0.2566	0.5635	0.098*
C3	0.39140 (18)	0.9208 (7)	0.9065 (5)	0.0704 (11)
H3	0.4214	0.8717	0.9694	0.084*
C12	0.06136 (19)	0.5340 (10)	0.6729 (5)	0.0851 (14)
H12	0.0280	0.5786	0.7160	0.102*

	U11	U22	U33	U12	U13	U23
Br1	0.0702 (4)	0.0749 (4)	0.1796 (7)	−0.0166 (2)	0.0112 (4)	−0.0221 (3)
O1	0.0774 (17)	0.0477 (13)	0.0385 (12)	−0.0068 (12)	0.0028 (11)	0.0028 (10)
C7	0.062 (2)	0.0424 (17)	0.0345 (16)	0.0026 (15)	0.0049 (15)	−0.0055 (13)
C9	0.059 (2)	0.0450 (18)	0.0493 (18)	0.0008 (16)	−0.0007 (16)	0.0039 (15)
O2	0.0772 (19)	0.0527 (14)	0.0812 (18)	0.0004 (13)	0.0136 (15)	−0.0171 (13)
N1	0.071 (2)	0.0511 (15)	0.0340 (14)	−0.0087 (14)	0.0044 (13)	0.0005 (12)
C1	0.064 (2)	0.0451 (17)	0.0381 (16)	−0.0018 (15)	0.0080 (15)	−0.0056 (14)
C6	0.072 (2)	0.0474 (19)	0.0498 (19)	−0.0078 (17)	−0.0011 (17)	−0.0017 (15)
C8	0.061 (2)	0.0484 (18)	0.0405 (16)	0.0038 (16)	−0.0009 (15)	0.0046 (14)
C5	0.088 (3)	0.048 (2)	0.068 (2)	−0.0111 (19)	0.019 (2)	−0.0034 (17)
C2	0.069 (2)	0.052 (2)	0.060 (2)	0.0022 (18)	−0.0012 (19)	−0.0004 (16)
C4	0.062 (2)	0.056 (2)	0.082 (3)	−0.0074 (19)	0.012 (2)	−0.014 (2)
C13	0.075 (3)	0.075 (3)	0.056 (2)	0.010 (2)	0.0069 (19)	−0.0066 (18)
C10	0.072 (3)	0.065 (2)	0.070 (2)	−0.011 (2)	−0.007 (2)	−0.005 (2)
C11	0.062 (3)	0.099 (4)	0.081 (3)	−0.015 (2)	−0.013 (2)	0.007 (3)
C3	0.062 (2)	0.062 (2)	0.086 (3)	0.001 (2)	−0.004 (2)	−0.013 (2)
C12	0.056 (3)	0.119 (4)	0.081 (3)	0.010 (3)	0.005 (2)	0.005 (3)

Br1—C4	1.895 (4)	C8—C13	1.384 (5)
O1—C7	1.239 (4)	C5—C4	1.365 (7)
C7—N1	1.334 (4)	C5—H5	0.9300
C7—C1	1.497 (5)	C2—C3	1.383 (6)
C9—O2	1.357 (4)	C2—H2	0.9300
C9—C10	1.380 (5)	C4—C3	1.374 (6)
C9—C8	1.384 (5)	C13—C12	1.375 (7)
O2—HO2	0.8200	C13—H13	0.9300
N1—C8	1.423 (5)	C10—C11	1.378 (7)
N1—H1	0.8600	C10—H10	0.9300
C1—C2	1.377 (5)	C11—C12	1.372 (7)
C1—C6	1.388 (5)	C11—H11	0.9300
C6—C5	1.387 (6)	C3—H3	0.9300
C6—H6	0.9300	C12—H12	0.9300
O1—C7—N1	122.0 (3)	C1—C2—C3	121.1 (4)
O1—C7—C1	120.9 (3)	C1—C2—H2	119.4
N1—C7—C1	117.2 (3)	C3—C2—H2	119.4
O2—C9—C10	123.4 (3)	C5—C4—C3	121.6 (4)
O2—C9—C8	116.7 (3)	C5—C4—Br1	118.7 (3)
C10—C9—C8	119.9 (4)	C3—C4—Br1	119.7 (3)
C9—O2—HO2	109.5	C12—C13—C8	120.3 (4)
C7—N1—C8	122.9 (3)	C12—C13—H13	119.9
C7—N1—H1	118.6	C8—C13—H13	119.9
C8—N1—H1	118.6	C11—C10—C9	120.1 (4)
C2—C1—C6	119.2 (3)	C11—C10—H10	120.0
C2—C1—C7	119.0 (3)	C9—C10—H10	120.0
C6—C1—C7	121.7 (3)	C12—C11—C10	120.2 (4)
C5—C6—C1	119.9 (4)	C12—C11—H11	119.9
C5—C6—H6	120.1	C10—C11—H11	119.9
C1—C6—H6	120.1	C4—C3—C2	118.6 (4)
C9—C8—C13	119.4 (4)	C4—C3—H3	120.7
C9—C8—N1	119.0 (3)	C2—C3—H3	120.7
C13—C8—N1	121.5 (3)	C11—C12—C13	120.1 (4)
C4—C5—C6	119.6 (4)	C11—C12—H12	120.0
C4—C5—H5	120.2	C13—C12—H12	120.0
C6—C5—H5	120.2
O1—C7—N1—C8	0.8 (5)	C6—C1—C2—C3	−0.3 (5)
C1—C7—N1—C8	−179.6 (3)	C7—C1—C2—C3	−178.8 (3)
O1—C7—C1—C2	24.5 (5)	C6—C5—C4—C3	0.7 (6)
N1—C7—C1—C2	−155.1 (3)	C6—C5—C4—Br1	−178.2 (3)
O1—C7—C1—C6	−153.9 (3)	C9—C8—C13—C12	0.3 (6)
N1—C7—C1—C6	26.5 (4)	N1—C8—C13—C12	178.8 (4)
C2—C1—C6—C5	0.3 (5)	O2—C9—C10—C11	−178.0 (4)
C7—C1—C6—C5	178.7 (3)	C8—C9—C10—C11	1.3 (6)
O2—C9—C8—C13	177.9 (3)	C9—C10—C11—C12	−0.1 (7)
C10—C9—C8—C13	−1.4 (5)	C5—C4—C3—C2	−0.8 (6)
O2—C9—C8—N1	−0.7 (4)	Br1—C4—C3—C2	178.1 (3)
C10—C9—C8—N1	180.0 (3)	C1—C2—C3—C4	0.6 (6)
C7—N1—C8—C9	−107.5 (4)	C10—C11—C12—C13	−1.1 (7)
C7—N1—C8—C13	73.9 (5)	C8—C13—C12—C11	1.0 (7)
C1—C6—C5—C4	−0.5 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O2—HO2···O1i	0.82	2.00	2.682 (3)	141
N1—H1···O1ii	0.86	2.02	2.824 (3)	155
C6—H6···O2iii	0.93	2.56	3.458 (5)	164

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O2HO2O1i	0.82	2.00	2.682(3)	141
N1H1O1ii	0.86	2.02	2.824(3)	155
C6H6O2iii	0.93	2.56	3.458(5)	164

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