organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

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[Singh, R. B., Jain, P. & Singh, R. P. (1982). Talanta, 29, 77-84.]); Salem (1998[Salem, A. A. (1998). Microchem. J. 60, 51-66.]); Carcelli et al. (1995[Carcelli, M., Mazza, P., Pelizzi, G. & Zani, F. (1995). J. Inorg. Biochem. 57, 43-62.]).

[Scheme 1]

Experimental

Crystal data
  • C13H9BrO2

  • Mr = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.604, Tmax = 0.807

  • 5479 measured reflections

  • 1933 independent reflections

  • 1578 reflections with I > 2σ(I)

  • Rint = 0.027

Refinement
  • R[F2 > 2σ(F2)] = 0.029

  • wR(F2) = 0.072

  • S = 1.03

  • 1933 reflections

  • 146 parameters

  • H-atom parameters constrained

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.52 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); data reduction: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


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.

Refinement top

All H atoms were positioned geometrically and treated as riding on their parent atoms,with C—H(aromatic) = 0.93 Å, O—H = 0.82 Å, and with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O).

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
[Figure 1] Fig. 1. The molecular structure of compound (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] 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
C13H9BrO2F(000) = 552
Mr = 277.11Dx = 1.681 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2043 reflections
a = 15.9510 (18) Åθ = 2.7–23.4°
b = 5.8956 (6) ŵ = 3.73 mm1
c = 12.1260 (14) ÅT = 298 K
β = 106.166 (2)°Block, yellow
V = 1095.2 (2) Å30.15 × 0.10 × 0.06 mm
Z = 4
Data collection top
Siemens SMART CCD area-detector
diffractometer
1933 independent reflections
Radiation source: fine-focus sealed tube1578 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ϕ and ω scansθmax = 25.1°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1819
Tmin = 0.604, Tmax = 0.807k = 47
5479 measured reflectionsl = 1414
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)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0296P)2 + 0.7566P]
where P = (Fo2 + 2Fc2)/3
1933 reflections(Δ/σ)max < 0.001
146 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.52 e Å3
Crystal data top
C13H9BrO2V = 1095.2 (2) Å3
Mr = 277.11Z = 4
Monoclinic, P21/cMo Kα radiation
a = 15.9510 (18) ŵ = 3.73 mm1
b = 5.8956 (6) ÅT = 298 K
c = 12.1260 (14) Å0.15 × 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)
Tmin = 0.604, Tmax = 0.807Rint = 0.027
5479 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0290 restraints
wR(F2) = 0.073H-atom parameters constrained
S = 1.03Δρmax = 0.33 e Å3
1933 reflectionsΔρmin = 0.52 e Å3
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
xyzUiso*/Ueq
Br10.42247 (2)0.27591 (5)0.49702 (3)0.05526 (14)
O10.28452 (15)0.5186 (4)0.70204 (17)0.0548 (6)
H10.25280.59740.65170.082*
O20.18991 (14)0.6145 (4)0.49878 (17)0.0537 (6)
C10.31010 (19)0.3343 (5)0.6540 (2)0.0404 (7)
C20.27504 (17)0.2828 (4)0.5366 (2)0.0330 (6)
C30.30905 (17)0.0971 (4)0.4914 (2)0.0336 (6)
H30.28770.06160.41390.040*
C40.37381 (18)0.0324 (5)0.5610 (2)0.0384 (6)
C50.40544 (19)0.0138 (6)0.6778 (3)0.0493 (8)
H50.44780.07890.72480.059*
C60.37369 (19)0.1969 (6)0.7229 (2)0.0485 (8)
H60.39520.22920.80080.058*
C70.20810 (18)0.4294 (5)0.4636 (2)0.0362 (6)
C80.16079 (17)0.3613 (5)0.3442 (2)0.0340 (6)
C90.15422 (19)0.5167 (5)0.2563 (2)0.0415 (7)
H90.18160.65690.27180.050*
C100.1068 (2)0.4626 (6)0.1452 (3)0.0503 (8)
H100.10420.56460.08580.060*
C110.0636 (2)0.2594 (6)0.1225 (3)0.0510 (8)
H110.03100.22500.04810.061*
C120.06851 (19)0.1062 (5)0.2098 (3)0.0466 (7)
H120.03810.03000.19420.056*
C130.11812 (18)0.1530 (5)0.3204 (2)0.0385 (6)
H130.12300.04640.37840.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0478 (2)0.0490 (2)0.0675 (2)0.01286 (15)0.01368 (16)0.00212 (16)
O10.0628 (15)0.0608 (15)0.0403 (11)0.0066 (11)0.0136 (11)0.0127 (10)
O20.0641 (15)0.0420 (13)0.0519 (13)0.0133 (10)0.0108 (11)0.0070 (10)
C10.0385 (16)0.0481 (17)0.0381 (15)0.0056 (13)0.0162 (13)0.0043 (13)
C20.0326 (14)0.0341 (15)0.0329 (13)0.0019 (11)0.0102 (11)0.0019 (11)
C30.0336 (15)0.0363 (15)0.0309 (14)0.0059 (12)0.0091 (12)0.0005 (12)
C40.0330 (15)0.0396 (16)0.0450 (16)0.0014 (12)0.0146 (13)0.0027 (13)
C50.0364 (17)0.065 (2)0.0425 (17)0.0083 (15)0.0039 (13)0.0110 (15)
C60.0390 (17)0.073 (2)0.0306 (15)0.0016 (16)0.0054 (13)0.0008 (15)
C70.0400 (16)0.0324 (15)0.0399 (15)0.0013 (12)0.0172 (13)0.0024 (12)
C80.0312 (14)0.0339 (15)0.0377 (15)0.0057 (12)0.0109 (12)0.0017 (12)
C90.0457 (18)0.0331 (16)0.0476 (17)0.0047 (13)0.0160 (14)0.0075 (13)
C100.055 (2)0.057 (2)0.0378 (17)0.0142 (16)0.0116 (15)0.0143 (15)
C110.0438 (17)0.064 (2)0.0393 (16)0.0131 (16)0.0013 (13)0.0034 (16)
C120.0351 (16)0.0453 (18)0.0565 (19)0.0009 (13)0.0079 (14)0.0071 (15)
C130.0360 (15)0.0381 (16)0.0421 (16)0.0035 (12)0.0117 (13)0.0056 (13)
Geometric parameters (Å, º) top
Br1—C41.898 (3)C6—H60.9300
O1—C11.348 (3)C7—C81.489 (4)
O1—H10.8200C8—C91.388 (4)
O2—C71.235 (3)C8—C131.395 (4)
C1—C61.382 (4)C9—C101.386 (4)
C1—C21.411 (4)C9—H90.9300
C2—C31.400 (4)C10—C111.371 (4)
C2—C71.464 (4)C10—H100.9300
C3—C41.370 (4)C11—C121.377 (4)
C3—H30.9300C11—H110.9300
C4—C51.391 (4)C12—C131.382 (4)
C5—C61.370 (4)C12—H120.9300
C5—H50.9300C13—H130.9300
C1—O1—H1109.5O2—C7—C8118.0 (2)
O1—C1—C6118.1 (3)C2—C7—C8121.0 (2)
O1—C1—C2121.8 (3)C9—C8—C13119.6 (3)
C6—C1—C2120.1 (3)C9—C8—C7118.6 (2)
C3—C2—C1118.4 (2)C13—C8—C7121.6 (2)
C3—C2—C7121.4 (2)C10—C9—C8120.0 (3)
C1—C2—C7120.0 (2)C10—C9—H9120.0
C4—C3—C2120.1 (2)C8—C9—H9120.0
C4—C3—H3119.9C11—C10—C9120.3 (3)
C2—C3—H3119.9C11—C10—H10119.9
C3—C4—C5121.1 (3)C9—C10—H10119.9
C3—C4—Br1119.5 (2)C10—C11—C12120.1 (3)
C5—C4—Br1119.4 (2)C10—C11—H11120.0
C6—C5—C4119.4 (3)C12—C11—H11120.0
C6—C5—H5120.3C11—C12—C13120.6 (3)
C4—C5—H5120.3C11—C12—H12119.7
C5—C6—C1120.8 (3)C13—C12—H12119.7
C5—C6—H6119.6C12—C13—C8119.4 (3)
C1—C6—H6119.6C12—C13—H13120.3
O2—C7—C2121.0 (2)C8—C13—H13120.3
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.821.852.569 (3)146
C3—H3···O1i0.932.603.488 (3)160
C12—H12···Cg1ii0.932.933.596 (3)130
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC13H9BrO2
Mr277.11
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)15.9510 (18), 5.8956 (6), 12.1260 (14)
β (°) 106.166 (2)
V3)1095.2 (2)
Z4
Radiation typeMo Kα
µ (mm1)3.73
Crystal size (mm)0.15 × 0.10 × 0.06
Data collection
DiffractometerSiemens SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.604, 0.807
No. of measured, independent and
observed [I > 2σ(I)] reflections
5479, 1933, 1578
Rint0.027
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.029, 0.073, 1.03
No. of reflections1933
No. of parameters146
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
O1—H1···O20.821.852.569 (3)146
C3—H3···O1i0.932.603.488 (3)160
C12—H12···Cg1ii0.932.933.596 (3)130
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x, y1/2, z+1/2.
 

Acknowledgements

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

References

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

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ISSN: 2056-9890
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