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

Zheng, C.-Z.; Ji, C.-Y.; Chang, X.-L.; Zhang, L.-Q.

doi:10.1107/S160053680803969X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2486

doi:10.1107/S160053680803969X

Open

access

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

Chang-Zheng Zheng,^a Chang-You Ji,^a ^* Xiu-Li Chang ^b and Li-Qin Zhang ^a

^aCollege of Environmental and Chemical Engineering, Xi'an Polytechnic University, 710048 Xi'an, Shaanxi, People's Republic of China, and ^bDepartment of Materials Science and Chemical Engineering, Sichuan University of Science and Engineering , 643000 Zigong, Sichuan, People's Republic of China
^*Correspondence e-mail: jichangyou789456@126.com

(Received 22 November 2008; accepted 25 November 2008; online 29 November 2008)

In the title compound, C₁₃H₉BrO₂, the dihedral angle between the aromatic ring planes is 53.6 (1)°. The crystal structure is stabilized by intramolecular O—H⋯O and intermolecular C—H⋯O hydrogen bonding and C—H⋯π interactions.

Related literature

For the ability of aroylhydrazones to coordinate to metal ions and their biological activity, see: Singh et al. (1982 ); Salem (1998 ); Carcelli et al. (1995 ).

Experimental

Crystal data

C₁₃H₉BrO₂
M_r = 277.11
Monoclinic, P 2₁ /c
a = 15.9510 (18) Å
b = 5.8956 (6) Å
c = 12.1260 (14) Å
β = 106.166 (2)°
V = 1095.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 3.73 mm⁻¹
T = 298 K
0.15 × 0.10 × 0.06 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.604, T_max = 0.807
5479 measured reflections
1933 independent reflections
1578 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.072
S = 1.03
1933 reflections
146 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.82	1.85	2.569 (3)	146
C3—H3⋯O1ⁱ	0.93	2.60	3.488 (3)	160
C12—H12⋯Cg1ⁱⁱ	0.93	2.93	3.596 (3)	130
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg1 is the centroid of the C8–C13 ring.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680803969X/at2684sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680803969X/at2684Isup2.hkl

checkCIF report

Comment top

The chemistry of aroylhydrazones continues to attract much attention due to their coordination ability to metal ions (Singh et al., 1982; Salem, 1998) and their biological activity (Singh et al., 1982; Carcelli et al., 1995). As an extension of work on the structural characterization of aroylhydrazone derivatives, the title compound, (I), was synthesized and its crystal structure is reported here.

The title molecule displays a trans conformation with respect to the C7=O2 double bond (Fig. 1). The crystal structure is stabilized by intramolecular O—H···O and intermolecular C—H···O hydrogen bonding and C-H···π interactions (Table 1. and Fig. 2).

Related literature top

For the ability of aroylhydrazones to coordinate to metal ions and their biological activity, see: Singh et al. (1982); Salem (1998); Carcelli et al. (1995). Cg1 is the centroid of the C8–C13 ring.

Experimental top

The benzoyl chloride (0.01 mol, 1.4057 g) and the 4-bromophenol, heated up in the oil bath, the reaction mixture was refluxed for 6 h with stirring. Then anhydrous aluminium trichloride (3 mol, 1:3) was added, the backflow agitation responds for 4 h (yield 80%). The compound (2.0 mmol, 0.67 g) was dissolved in dimethylformamide (30 ml) and kept at room temperature for 30 d to obtain brown single crystals suitable for X-ray diffraction.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of compound (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The crystal packing of (I), viewed down the b axis. Dashed lines show intra-and intermolecular hydrogen bonds.

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

Crystal data top

C₁₃H₉BrO₂	F(000) = 552
M_r = 277.11	D_x = 1.681 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2043 reflections
a = 15.9510 (18) Å	θ = 2.7–23.4°
b = 5.8956 (6) Å	µ = 3.73 mm⁻¹
c = 12.1260 (14) Å	T = 298 K
β = 106.166 (2)°	Block, yellow
V = 1095.2 (2) Å³	0.15 × 0.10 × 0.06 mm
Z = 4

Data collection top

Siemens SMART CCD area-detector diffractometer	1933 independent reflections
Radiation source: fine-focus sealed tube	1578 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→19
T_min = 0.604, T_max = 0.807	k = −4→7
5479 measured reflections	l = −14→14

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.073	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0296P)² + 0.7566P] where P = (F_o² + 2F_c²)/3
1933 reflections	(Δ/σ)_max < 0.001
146 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

C₁₃H₉BrO₂	V = 1095.2 (2) Å³
M_r = 277.11	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.9510 (18) Å	µ = 3.73 mm⁻¹
b = 5.8956 (6) Å	T = 298 K
c = 12.1260 (14) Å	0.15 × 0.10 × 0.06 mm
β = 106.166 (2)°

Data collection top

Siemens SMART CCD area-detector diffractometer	1933 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1578 reflections with I > 2σ(I)
T_min = 0.604, T_max = 0.807	R_int = 0.027
5479 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.073	H-atom parameters constrained
S = 1.03	Δρ_max = 0.33 e Å⁻³
1933 reflections	Δρ_min = −0.52 e Å⁻³
146 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)	−0.27591 (5)	0.49702 (3)	0.05526 (14)
O1	0.28452 (15)	0.5186 (4)	0.70204 (17)	0.0548 (6)
H1	0.2528	0.5974	0.6517	0.082*
O2	0.18991 (14)	0.6145 (4)	0.49878 (17)	0.0537 (6)
C1	0.31010 (19)	0.3343 (5)	0.6540 (2)	0.0404 (7)
C2	0.27504 (17)	0.2828 (4)	0.5366 (2)	0.0330 (6)
C3	0.30905 (17)	0.0971 (4)	0.4914 (2)	0.0336 (6)
H3	0.2877	0.0616	0.4139	0.040*
C4	0.37381 (18)	−0.0324 (5)	0.5610 (2)	0.0384 (6)
C5	0.40544 (19)	0.0138 (6)	0.6778 (3)	0.0493 (8)
H5	0.4478	−0.0789	0.7248	0.059*
C6	0.37369 (19)	0.1969 (6)	0.7229 (2)	0.0485 (8)
H6	0.3952	0.2292	0.8008	0.058*
C7	0.20810 (18)	0.4294 (5)	0.4636 (2)	0.0362 (6)
C8	0.16079 (17)	0.3613 (5)	0.3442 (2)	0.0340 (6)
C9	0.15422 (19)	0.5167 (5)	0.2563 (2)	0.0415 (7)
H9	0.1816	0.6569	0.2718	0.050*
C10	0.1068 (2)	0.4626 (6)	0.1452 (3)	0.0503 (8)
H10	0.1042	0.5646	0.0858	0.060*
C11	0.0636 (2)	0.2594 (6)	0.1225 (3)	0.0510 (8)
H11	0.0310	0.2250	0.0481	0.061*
C12	0.06851 (19)	0.1062 (5)	0.2098 (3)	0.0466 (7)
H12	0.0381	−0.0300	0.1942	0.056*
C13	0.11812 (18)	0.1530 (5)	0.3204 (2)	0.0385 (6)
H13	0.1230	0.0464	0.3784	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0478 (2)	0.0490 (2)	0.0675 (2)	0.01286 (15)	0.01368 (16)	−0.00212 (16)
O1	0.0628 (15)	0.0608 (15)	0.0403 (11)	0.0066 (11)	0.0136 (11)	−0.0127 (10)
O2	0.0641 (15)	0.0420 (13)	0.0519 (13)	0.0133 (10)	0.0108 (11)	−0.0070 (10)
C1	0.0385 (16)	0.0481 (17)	0.0381 (15)	−0.0056 (13)	0.0162 (13)	−0.0043 (13)
C2	0.0326 (14)	0.0341 (15)	0.0329 (13)	−0.0019 (11)	0.0102 (11)	0.0019 (11)
C3	0.0336 (15)	0.0363 (15)	0.0309 (14)	−0.0059 (12)	0.0091 (12)	−0.0005 (12)
C4	0.0330 (15)	0.0396 (16)	0.0450 (16)	0.0014 (12)	0.0146 (13)	0.0027 (13)
C5	0.0364 (17)	0.065 (2)	0.0425 (17)	0.0083 (15)	0.0039 (13)	0.0110 (15)
C6	0.0390 (17)	0.073 (2)	0.0306 (15)	0.0016 (16)	0.0054 (13)	0.0008 (15)
C7	0.0400 (16)	0.0324 (15)	0.0399 (15)	−0.0013 (12)	0.0172 (13)	0.0024 (12)
C8	0.0312 (14)	0.0339 (15)	0.0377 (15)	0.0057 (12)	0.0109 (12)	0.0017 (12)
C9	0.0457 (18)	0.0331 (16)	0.0476 (17)	0.0047 (13)	0.0160 (14)	0.0075 (13)
C10	0.055 (2)	0.057 (2)	0.0378 (17)	0.0142 (16)	0.0116 (15)	0.0143 (15)
C11	0.0438 (17)	0.064 (2)	0.0393 (16)	0.0131 (16)	0.0013 (13)	−0.0034 (16)
C12	0.0351 (16)	0.0453 (18)	0.0565 (19)	−0.0009 (13)	0.0079 (14)	−0.0071 (15)
C13	0.0360 (15)	0.0381 (16)	0.0421 (16)	0.0035 (12)	0.0117 (13)	0.0056 (13)

Geometric parameters (Å, º) top

Br1—C4	1.898 (3)	C6—H6	0.9300
O1—C1	1.348 (3)	C7—C8	1.489 (4)
O1—H1	0.8200	C8—C9	1.388 (4)
O2—C7	1.235 (3)	C8—C13	1.395 (4)
C1—C6	1.382 (4)	C9—C10	1.386 (4)
C1—C2	1.411 (4)	C9—H9	0.9300
C2—C3	1.400 (4)	C10—C11	1.371 (4)
C2—C7	1.464 (4)	C10—H10	0.9300
C3—C4	1.370 (4)	C11—C12	1.377 (4)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.391 (4)	C12—C13	1.382 (4)
C5—C6	1.370 (4)	C12—H12	0.9300
C5—H5	0.9300	C13—H13	0.9300

C1—O1—H1	109.5	O2—C7—C8	118.0 (2)
O1—C1—C6	118.1 (3)	C2—C7—C8	121.0 (2)
O1—C1—C2	121.8 (3)	C9—C8—C13	119.6 (3)
C6—C1—C2	120.1 (3)	C9—C8—C7	118.6 (2)
C3—C2—C1	118.4 (2)	C13—C8—C7	121.6 (2)
C3—C2—C7	121.4 (2)	C10—C9—C8	120.0 (3)
C1—C2—C7	120.0 (2)	C10—C9—H9	120.0
C4—C3—C2	120.1 (2)	C8—C9—H9	120.0
C4—C3—H3	119.9	C11—C10—C9	120.3 (3)
C2—C3—H3	119.9	C11—C10—H10	119.9
C3—C4—C5	121.1 (3)	C9—C10—H10	119.9
C3—C4—Br1	119.5 (2)	C10—C11—C12	120.1 (3)
C5—C4—Br1	119.4 (2)	C10—C11—H11	120.0
C6—C5—C4	119.4 (3)	C12—C11—H11	120.0
C6—C5—H5	120.3	C11—C12—C13	120.6 (3)
C4—C5—H5	120.3	C11—C12—H12	119.7
C5—C6—C1	120.8 (3)	C13—C12—H12	119.7
C5—C6—H6	119.6	C12—C13—C8	119.4 (3)
C1—C6—H6	119.6	C12—C13—H13	120.3
O2—C7—C2	121.0 (2)	C8—C13—H13	120.3

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.85	2.569 (3)	146
C3—H3···O1ⁱ	0.93	2.60	3.488 (3)	160
C12—H12···Cg1ⁱⁱ	0.93	2.93	3.596 (3)	130

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₉BrO₂
M_r	277.11
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	15.9510 (18), 5.8956 (6), 12.1260 (14)
β (°)	106.166 (2)
V (Å³)	1095.2 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.73
Crystal size (mm)	0.15 × 0.10 × 0.06

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.604, 0.807
No. of measured, independent and observed [I > 2σ(I)] reflections	5479, 1933, 1578
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.073, 1.03
No. of reflections	1933
No. of parameters	146
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.52

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.85	2.569 (3)	146
C3—H3···O1ⁱ	0.93	2.60	3.488 (3)	160
C12—H12···Cg1ⁱⁱ	0.93	2.93	3.596 (3)	130

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x, y−1/2, −z+1/2.

Acknowledgements

This project was supported by the Postgraduate Foundation of Xi'an Polytechnic University (No. Y05–2–09)

References

Carcelli, M., Mazza, P., Pelizzi, G. & Zani, F. (1995). J. Inorg. Biochem. 57, 43–62. CrossRef CAS PubMed Web of Science Google Scholar
Salem, A. A. (1998). Microchem. J. 60, 51–66. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Singh, R. B., Jain, P. & Singh, R. P. (1982). Talanta, 29, 77–84. CrossRef PubMed CAS Web of Science Google Scholar