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

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

doi:10.1107/S1600536808027578

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o1873

doi:10.1107/S1600536808027578

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

Feng-Ke Yang,^a ^* Yi-Ning Ding,^a Wei Cheng ^b and Ke Xu ^b

^aCollege of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, People's Republic of China, and ^bKey Laboratory of Advanced Materials, Qingdao University of Science and Technology, Qingdao 266042, People's Republic of China
^*Correspondence e-mail: minicocorain@163.com

(Received 26 August 2008; accepted 28 August 2008; online 6 September 2008)

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, P 2₁ /c
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[F² > 2σ(F²)] = 0.035
wR(F²) = 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

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) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

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.

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

	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.

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

Crystal data top

C₁₃H₉BrO₂	F(000) = 552
M_r = 277.10	D_x = 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 top

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

Refinement top

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(F_o²) + (0.0519P)² + 0.0875P] where P = (F_o² + 2F_c²)/3
2292 reflections	(Δ/σ)_max < 0.001
145 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.61 e Å⁻³

Crystal data top

C₁₃H₉BrO₂	V = 1092.6 (4) Å³
M_r = 277.10	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.938 (3) Å	µ = 3.74 mm⁻¹
b = 5.8929 (12) Å	T = 295 K
c = 12.111 (2) Å	0.30 × 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)
T_min = 0.417, T_max = 0.689	R_int = 0.026
4878 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.08	Δρ_max = 0.36 e Å⁻³
2292 reflections	Δρ_min = −0.61 e Å⁻³
145 parameters

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

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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, º) top

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, º) top

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) x, −y−1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₉BrO₂
M_r	277.10
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	15.938 (3), 5.8929 (12), 12.111 (2)
β (°)	106.15 (3)
V (Å³)	1092.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.74
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART 1K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.417, 0.689
No. of measured, independent and observed [I > 2σ(I)] reflections	4878, 2292, 1767
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.633

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.101, 1.08
No. of reflections	2292
No. of parameters	145
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.61

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008) and local programs.

Selected bond lengths (Å) top

Br1—C12	1.896 (3)	O2—C9	1.348 (4)
O1—C7	1.231 (3)

Hydrogen-bond geometry (Å, º) top

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) x, −y−1/2, z−1/2.

Acknowledgements

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

References

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