(5-Bromo-2-hydroxy-phen-yl)(phen-yl)methanone.

In the title compound, C(13)H(9)BrO(2), the mol-ecular conformation is stabilized by an intra-molecular O-H⋯O hydrogen bond. In the crystal structure, weak inter-molecular C-H⋯O hydrogen-bonding inter-actions link the mol-ecules into chains along the c-axis direction.

Related literature

For related literature, see: Dale et al. (1999 ▶); Sridhar & Saravanan (2001 ▶); Wiktor et al. (2000 ▶); Hester et al. (2001 ▶); Idrees et al. (2001 ▶); Zhou (2006 ▶).

Experimental

Crystal data

C13H9BrO2

M = 277.10

Monoclinic,

a = 15.938 (3) Å

b = 5.8929 (12) Å

c = 12.111 (2) Å

β = 106.15 (3)°

V = 1092.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 3.74 mm−1

T = 295 (2) K

0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.417, T max = 0.689

4878 measured reflections

2292 independent reflections

1767 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.101

S = 1.08

2292 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.61 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808027578/at2622sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027578/at2622Isup2.hkl

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

C13H9BrO2	F(000) = 552
Mr = 277.10	Dx = 1.685 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1025 reflections
a = 15.938 (3) Å	θ = 1.3–27.0°
b = 5.8929 (12) Å	µ = 3.74 mm−1
c = 12.111 (2) Å	T = 295 K
β = 106.15 (3)°	Block, yellow
V = 1092.6 (4) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Bruker SMART 1K CCD area-detector diffractometer	2292 independent reflections
Radiation source: fine-focus sealed tube	1767 reflections with I > 2σ(I)
graphite	Rint = 0.026
Thin–slice ω scans	θmax = 26.7°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −19→19
Tmin = 0.417, Tmax = 0.689	k = −7→6
4878 measured reflections	l = −14→15

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0519P)2 + 0.0875P] where P = (Fo2 + 2Fc2)/3
2292 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.61 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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	0.42247 (2)	0.27571 (6)	0.49704 (3)	0.06162 (16)
O1	0.18993 (15)	−0.6147 (4)	0.49901 (19)	0.0609 (6)
O2	0.28487 (15)	−0.5189 (4)	0.70244 (19)	0.0613 (6)
H2A	0.2498	−0.5930	0.6532	0.092*
C1	0.11815 (19)	−0.1537 (5)	0.3198 (3)	0.0457 (7)
H1A	0.1235	−0.0469	0.3779	0.055*
C2	0.06832 (19)	−0.1057 (5)	0.2101 (3)	0.0518 (7)
H2B	0.0378	0.0305	0.1950	0.062*
C3	0.0635 (2)	−0.2590 (5)	0.1225 (3)	0.0580 (9)
H3A	0.0308	−0.2246	0.0480	0.070*
C4	0.1071 (2)	−0.4629 (5)	0.1454 (3)	0.0560 (8)
H4A	0.1049	−0.5649	0.0861	0.067*
C5	0.1541 (2)	−0.5160 (5)	0.2561 (3)	0.0484 (7)
H5A	0.1816	−0.6563	0.2718	0.058*
C6	0.16053 (17)	−0.3611 (5)	0.3442 (2)	0.0398 (6)
C7	0.20826 (18)	−0.4302 (5)	0.4640 (3)	0.0432 (6)
C8	0.27492 (18)	−0.2824 (4)	0.5359 (3)	0.0387 (6)
C9	0.30999 (19)	−0.3350 (5)	0.6535 (3)	0.0469 (7)
C10	0.3733 (2)	−0.1974 (6)	0.7230 (3)	0.0554 (8)
H10A	0.3943	−0.2292	0.8011	0.066*
C11	0.4053 (2)	−0.0134 (6)	0.6774 (3)	0.0564 (8)
H11A	0.4476	0.0795	0.7245	0.068*
C12	0.37446 (18)	0.0319 (5)	0.5617 (3)	0.0453 (7)
C13	0.30905 (17)	−0.0964 (5)	0.4910 (2)	0.0408 (6)
H13A	0.2876	−0.0595	0.4136	0.049*

	U11	U22	U33	U12	U13	U23
Br1	0.0542 (2)	0.0546 (2)	0.0743 (3)	−0.01334 (14)	0.01486 (18)	0.00225 (16)
O1	0.0721 (15)	0.0486 (12)	0.0597 (14)	−0.0165 (11)	0.0143 (12)	0.0081 (10)
O2	0.0680 (15)	0.0658 (14)	0.0489 (13)	−0.0075 (11)	0.0140 (11)	0.0156 (11)
C1	0.0468 (16)	0.0418 (14)	0.0496 (18)	−0.0017 (13)	0.0151 (14)	−0.0040 (13)
C2	0.0443 (17)	0.0504 (17)	0.057 (2)	0.0004 (13)	0.0087 (14)	0.0051 (15)
C3	0.0526 (19)	0.072 (2)	0.0452 (18)	−0.0139 (16)	0.0063 (15)	0.0036 (16)
C4	0.065 (2)	0.0589 (19)	0.0454 (18)	−0.0105 (16)	0.0173 (16)	−0.0108 (15)
C5	0.0524 (18)	0.0421 (15)	0.0526 (18)	−0.0039 (13)	0.0174 (15)	−0.0071 (13)
C6	0.0377 (14)	0.0398 (14)	0.0428 (16)	−0.0044 (11)	0.0128 (12)	−0.0016 (12)
C7	0.0458 (16)	0.0391 (14)	0.0484 (17)	−0.0014 (12)	0.0194 (13)	−0.0020 (12)
C8	0.0360 (14)	0.0399 (14)	0.0414 (16)	0.0049 (11)	0.0126 (12)	−0.0018 (11)
C9	0.0442 (16)	0.0540 (16)	0.0450 (18)	0.0055 (13)	0.0165 (13)	0.0029 (13)
C10	0.0492 (18)	0.077 (2)	0.0365 (17)	0.0005 (16)	0.0067 (14)	0.0010 (15)
C11	0.0470 (18)	0.072 (2)	0.0476 (19)	−0.0087 (15)	0.0084 (14)	−0.0105 (16)
C12	0.0402 (15)	0.0461 (15)	0.0516 (18)	−0.0020 (12)	0.0160 (13)	−0.0031 (13)
C13	0.0392 (15)	0.0443 (15)	0.0387 (16)	0.0046 (11)	0.0105 (12)	−0.0001 (12)

Br1—C12	1.896 (3)	C5—C6	1.386 (4)
O1—C7	1.231 (3)	C5—H5A	0.9300
O2—C9	1.348 (4)	C6—C7	1.495 (4)
O2—H2A	0.8200	C7—C8	1.460 (4)
C1—C2	1.374 (4)	C8—C13	1.400 (4)
C1—C6	1.388 (4)	C8—C9	1.412 (4)
C1—H1A	0.9300	C9—C10	1.383 (4)
C2—C3	1.379 (5)	C10—C11	1.378 (4)
C2—H2B	0.9300	C10—H10A	0.9300
C3—C4	1.378 (4)	C11—C12	1.377 (4)
C3—H3A	0.9300	C11—H11A	0.9300
C4—C5	1.377 (4)	C12—C13	1.376 (4)
C4—H4A	0.9300	C13—H13A	0.9300
C9—O2—H2A	109.5	O1—C7—C6	118.0 (3)
C2—C1—C6	120.2 (3)	C8—C7—C6	120.4 (2)
C2—C1—H1A	119.9	C13—C8—C9	118.5 (3)
C6—C1—H1A	119.9	C13—C8—C7	122.2 (3)
C1—C2—C3	120.2 (3)	C9—C8—C7	119.3 (3)
C1—C2—H2B	119.9	O2—C9—C10	117.3 (3)
C3—C2—H2B	119.9	O2—C9—C8	122.5 (3)
C4—C3—C2	120.0 (3)	C10—C9—C8	120.2 (3)
C4—C3—H3A	120.0	C11—C10—C9	120.4 (3)
C2—C3—H3A	120.0	C11—C10—H10A	119.8
C5—C4—C3	120.1 (3)	C9—C10—H10A	119.8
C5—C4—H4A	120.0	C12—C11—C10	119.6 (3)
C3—C4—H4A	120.0	C12—C11—H11A	120.2
C4—C5—C6	120.2 (3)	C10—C11—H11A	120.2
C4—C5—H5A	119.9	C13—C12—C11	121.4 (3)
C6—C5—H5A	119.9	C13—C12—Br1	118.8 (2)
C5—C6—C1	119.2 (3)	C11—C12—Br1	119.8 (2)
C5—C6—C7	118.5 (3)	C12—C13—C8	119.8 (3)
C1—C6—C7	122.2 (3)	C12—C13—H13A	120.1
O1—C7—C8	121.6 (3)	C8—C13—H13A	120.1
C6—C1—C2—C3	−3.1 (5)	C6—C7—C8—C9	170.9 (2)
C1—C2—C3—C4	1.4 (5)	C13—C8—C9—O2	−175.9 (3)
C2—C3—C4—C5	1.4 (5)	C7—C8—C9—O2	0.6 (4)
C3—C4—C5—C6	−2.5 (5)	C13—C8—C9—C10	3.4 (4)
C4—C5—C6—C1	0.9 (4)	C7—C8—C9—C10	179.9 (3)
C4—C5—C6—C7	176.9 (3)	O2—C9—C10—C11	176.6 (3)
C2—C1—C6—C5	1.9 (4)	C8—C9—C10—C11	−2.8 (5)
C2—C1—C6—C7	−173.9 (3)	C9—C10—C11—C12	−0.5 (5)
C5—C6—C7—O1	−48.6 (4)	C10—C11—C12—C13	3.1 (5)
C1—C6—C7—O1	127.3 (3)	C10—C11—C12—Br1	−176.9 (2)
C5—C6—C7—C8	130.9 (3)	C11—C12—C13—C8	−2.4 (4)
C1—C6—C7—C8	−53.2 (4)	Br1—C12—C13—C8	177.60 (19)
O1—C7—C8—C13	166.7 (3)	C9—C8—C13—C12	−0.9 (4)
C6—C7—C8—C13	−12.8 (4)	C7—C8—C13—C12	−177.2 (2)
O1—C7—C8—C9	−9.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1	0.82	1.85	2.570 (3)	146
C13—H13A···O2i	0.93	2.59	3.475 (3)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O1	0.82	1.85	2.570 (3)	146
C13—H13A⋯O2i	0.93	2.59	3.475 (3)	160

Symmetry code: (i) .