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Acta Cryst. (2008). E64, o1873    [ doi:10.1107/S1600536808027578 ]

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

F.-K. Yang, Y.-N. Ding, W. Cheng and K. Xu

Abstract top

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.

Comment top

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.

Related literature top

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 top

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 top

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 Uiso =1.2 Ueq (C) and Uiso =1.5 Ueq (O).

Computing details top

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

Figures top
[Figure 1] Fig. 1. The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] Fig. 2. The packing of (I), viewed down the b axis.
(5-Bromo-2-hydroxyphenyl)(phenyl)methanone top
Crystal data top
C13H9BrO2F(000) = 552
Mr = 277.10Dx = 1.685 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1025 reflections
a = 15.938 (3) Åθ = 1.3–27.0°
b = 5.8929 (12) ŵ = 3.74 mm−1
c = 12.111 (2) ÅT = 295 K
β = 106.15 (3)°Block, yellow
V = 1092.6 (4) Å30.30 × 0.20 × 0.10 mm
Z = 4
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer		2292 independent reflections
Radiation source: fine-focus sealed tube1767 reflections with I > 2σ(I)
graphiteRint = 0.026
Thin–slice ω scansθmax = 26.7°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		h = −19→19
Tmin = 0.417, Tmax = 0.689k = −7→6
4878 measured reflectionsl = −14→15
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H-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 parametersΔρmax = 0.36 e Å−3
0 restraintsΔρmin = −0.61 e Å−3
Crystal data top
C13H9BrO2V = 1092.6 (4) Å3
Mr = 277.10Z = 4
Monoclinic, P21/cMo Kα radiation
a = 15.938 (3) ŵ = 3.74 mm−1
b = 5.8929 (12) ÅT = 295 K
c = 12.111 (2) Å0.30 × 0.20 × 0.10 mm
β = 106.15 (3)°
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer		2292 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		1767 reflections with I > 2σ(I)
Tmin = 0.417, Tmax = 0.689Rint = 0.026
4878 measured reflectionsθmax = 26.7°
Refinement top
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.101Δρmax = 0.36 e Å−3
S = 1.08Δρmin = −0.61 e Å−3
2292 reflectionsAbsolute structure: ?
145 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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 (Å2) top
xyzUiso*/Ueq
Br10.42247 (2)0.27571 (6)0.49704 (3)0.06162 (16)
O10.18993 (15)−0.6147 (4)0.49901 (19)0.0609 (6)
O20.28487 (15)−0.5189 (4)0.70244 (19)0.0613 (6)
H2A0.2498−0.59300.65320.092*
C10.11815 (19)−0.1537 (5)0.3198 (3)0.0457 (7)
H1A0.1235−0.04690.37790.055*
C20.06832 (19)−0.1057 (5)0.2101 (3)0.0518 (7)
H2B0.03780.03050.19500.062*
C30.0635 (2)−0.2590 (5)0.1225 (3)0.0580 (9)
H3A0.0308−0.22460.04800.070*
C40.1071 (2)−0.4629 (5)0.1454 (3)0.0560 (8)
H4A0.1049−0.56490.08610.067*
C50.1541 (2)−0.5160 (5)0.2561 (3)0.0484 (7)
H5A0.1816−0.65630.27180.058*
C60.16053 (17)−0.3611 (5)0.3442 (2)0.0398 (6)
C70.20826 (18)−0.4302 (5)0.4640 (3)0.0432 (6)
C80.27492 (18)−0.2824 (4)0.5359 (3)0.0387 (6)
C90.30999 (19)−0.3350 (5)0.6535 (3)0.0469 (7)
C100.3733 (2)−0.1974 (6)0.7230 (3)0.0554 (8)
H10A0.3943−0.22920.80110.066*
C110.4053 (2)−0.0134 (6)0.6774 (3)0.0564 (8)
H11A0.44760.07950.72450.068*
C120.37446 (18)0.0319 (5)0.5617 (3)0.0453 (7)
C130.30905 (17)−0.0964 (5)0.4910 (2)0.0408 (6)
H13A0.2876−0.05950.41360.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0542 (2)0.0546 (2)0.0743 (3)−0.01334 (14)0.01486 (18)0.00225 (16)
O10.0721 (15)0.0486 (12)0.0597 (14)−0.0165 (11)0.0143 (12)0.0081 (10)
O20.0680 (15)0.0658 (14)0.0489 (13)−0.0075 (11)0.0140 (11)0.0156 (11)
C10.0468 (16)0.0418 (14)0.0496 (18)−0.0017 (13)0.0151 (14)−0.0040 (13)
C20.0443 (17)0.0504 (17)0.057 (2)0.0004 (13)0.0087 (14)0.0051 (15)
C30.0526 (19)0.072 (2)0.0452 (18)−0.0139 (16)0.0063 (15)0.0036 (16)
C40.065 (2)0.0589 (19)0.0454 (18)−0.0105 (16)0.0173 (16)−0.0108 (15)
C50.0524 (18)0.0421 (15)0.0526 (18)−0.0039 (13)0.0174 (15)−0.0071 (13)
C60.0377 (14)0.0398 (14)0.0428 (16)−0.0044 (11)0.0128 (12)−0.0016 (12)
C70.0458 (16)0.0391 (14)0.0484 (17)−0.0014 (12)0.0194 (13)−0.0020 (12)
C80.0360 (14)0.0399 (14)0.0414 (16)0.0049 (11)0.0126 (12)−0.0018 (11)
C90.0442 (16)0.0540 (16)0.0450 (18)0.0055 (13)0.0165 (13)0.0029 (13)
C100.0492 (18)0.077 (2)0.0365 (17)0.0005 (16)0.0067 (14)0.0010 (15)
C110.0470 (18)0.072 (2)0.0476 (19)−0.0087 (15)0.0084 (14)−0.0105 (16)
C120.0402 (15)0.0461 (15)0.0516 (18)−0.0020 (12)0.0160 (13)−0.0031 (13)
C130.0392 (15)0.0443 (15)0.0387 (16)0.0046 (11)0.0105 (12)−0.0001 (12)
Geometric parameters (Å, °) top
Br1—C121.896 (3)C5—C61.386 (4)
O1—C71.231 (3)C5—H5A0.9300
O2—C91.348 (4)C6—C71.495 (4)
O2—H2A0.8200C7—C81.460 (4)
C1—C21.374 (4)C8—C131.400 (4)
C1—C61.388 (4)C8—C91.412 (4)
C1—H1A0.9300C9—C101.383 (4)
C2—C31.379 (5)C10—C111.378 (4)
C2—H2B0.9300C10—H10A0.9300
C3—C41.378 (4)C11—C121.377 (4)
C3—H3A0.9300C11—H11A0.9300
C4—C51.377 (4)C12—C131.376 (4)
C4—H4A0.9300C13—H13A0.9300
C9—O2—H2A109.5O1—C7—C6118.0 (3)
C2—C1—C6120.2 (3)C8—C7—C6120.4 (2)
C2—C1—H1A119.9C13—C8—C9118.5 (3)
C6—C1—H1A119.9C13—C8—C7122.2 (3)
C1—C2—C3120.2 (3)C9—C8—C7119.3 (3)
C1—C2—H2B119.9O2—C9—C10117.3 (3)
C3—C2—H2B119.9O2—C9—C8122.5 (3)
C4—C3—C2120.0 (3)C10—C9—C8120.2 (3)
C4—C3—H3A120.0C11—C10—C9120.4 (3)
C2—C3—H3A120.0C11—C10—H10A119.8
C5—C4—C3120.1 (3)C9—C10—H10A119.8
C5—C4—H4A120.0C12—C11—C10119.6 (3)
C3—C4—H4A120.0C12—C11—H11A120.2
C4—C5—C6120.2 (3)C10—C11—H11A120.2
C4—C5—H5A119.9C13—C12—C11121.4 (3)
C6—C5—H5A119.9C13—C12—Br1118.8 (2)
C5—C6—C1119.2 (3)C11—C12—Br1119.8 (2)
C5—C6—C7118.5 (3)C12—C13—C8119.8 (3)
C1—C6—C7122.2 (3)C12—C13—H13A120.1
O1—C7—C8121.6 (3)C8—C13—H13A120.1
C6—C1—C2—C3−3.1 (5)C6—C7—C8—C9170.9 (2)
C1—C2—C3—C41.4 (5)C13—C8—C9—O2−175.9 (3)
C2—C3—C4—C51.4 (5)C7—C8—C9—O20.6 (4)
C3—C4—C5—C6−2.5 (5)C13—C8—C9—C103.4 (4)
C4—C5—C6—C10.9 (4)C7—C8—C9—C10179.9 (3)
C4—C5—C6—C7176.9 (3)O2—C9—C10—C11176.6 (3)
C2—C1—C6—C51.9 (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—C133.1 (5)
C1—C6—C7—O1127.3 (3)C10—C11—C12—Br1−176.9 (2)
C5—C6—C7—C8130.9 (3)C11—C12—C13—C8−2.4 (4)
C1—C6—C7—C8−53.2 (4)Br1—C12—C13—C8177.60 (19)
O1—C7—C8—C13166.7 (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, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···O10.821.852.570 (3)146
C13—H13A···O2i0.932.593.475 (3)160
Symmetry codes: (i) x, −y−1/2, z−1/2.
Table 1
Selected geometric parameters (Å) top
Br1—C121.896 (3)O2—C91.348 (4)
O1—C71.231 (3)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···O10.821.852.570 (3)146
C13—H13A···O2i0.932.593.475 (3)160
Symmetry codes: (i) x, −y−1/2, z−1/2.
Acknowledgements top

The authors thank the Natural Science Foundation of Shandong Province (No. Q2006B02).

references
References top

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