(5-Bromo-2-hydroxy­phen­yl)(phen­yl)methanone

Abstract

In the title compound, C₁₃H₉BrO₂, the mol­ecular conformation is stabilized by an intra­molecular O—H⋯O hydrogen bond. In the crystal structure, weak inter­molecular C—H⋯O hydrogen-bonding inter­actions link the mol­ecules 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 _r = 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) ų

• 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

• Δρ_max = 0.36 e Å⁻³

• Δρ_min = −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.

Supplementary Material

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

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) .

supplementary crystallographic information

Comment

Monocondensed Schiff bases are attractive because of their intermediates in the synthesis of unsymmetrical multidentate Schiff base ligands and metal complexes, which serve as potential chelating agents and catalyst in synthesis and pharmaceutical fields (Hester et al., 2001). New examples are being tested for their antitumor, (Idrees et al., 2001). antimicroial and antiviral activities (Sridhar & Saravanan, 2001). We describe the structure of the title compound is a precursor of monocondensed Schiff bases.

In the title compound, bond lengths are slightly different from those in similar compounds. The C—Br bond length [1.896 (3) Å] is longer than others reported [1.865 (1) (Dale et al., 1999) and 1.884 (2)Å (Wiktor et al., 2000)]. Molecular conformation is stabilized by an intramolecular O—H···O hydrogen bond. In the crystal structure, weak intermolecular C—H···O hydrogen bonding interactions (Table 1) link the molecules into chains along the b-direction.

Experimental

5-Bromo-2-hydroxybenzophenone was prepared via the Fries rearrangement of p-bromophenyl benzoate at 433 K with AlCl₃ as the catalyst. The title compound was collected and washed with 10% diluted hydrochloric acid. Single crystals suitable for X-ray measurements were obtained by recrystallization from absolute ethanol and acetic ether (1:1,v/v) at room temperature.

Refinement

All H atoms were placed at calculated positions and allowed to ride on their attached atoms, with C—H distance = 0.93 Å and O—H = 0.82 Å, and with U_iso =1.2 U_eq (C) and U_iso =1.5 U_eq (O).

Figures

Fig. 1.

The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.

Fig. 2.

The packing of (I), viewed down the b axis.

Crystal data

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

Data collection

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

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

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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*

Atomic displacement parameters (Ų)

	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)

Geometric parameters (Å, °)

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)

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 codes: (i) x, −y−1/2, z−1/2.