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

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ISSN: 2056-9890

(4-Hy­dr­oxy-3-methyl­phen­yl)(phen­yl)methanone

aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India, and bDepartment of Chemistry, Yuvaraja's College, University of Mysore, Mysore 570 005, India
*Correspondence e-mail: mas@physics.uni-mysore.ac.in

(Received 7 September 2013; accepted 11 September 2013; online 18 September 2013)

In the title compound, C14H12O2, the benzene rings make a dihedral angle of 58.84 (12)°. In the crystal, mol­ecules are linked into chains along the b-axis direction by O—H⋯O hydrogen bonds. These chains are further linked by C—H⋯O hydrogen bonds, forming layers parallel to the bc plane.

Related literature

For the biological activity of benzo­phenone derivatives, see: Khanum et al. (2004[Khanum, S. A., Venu, T. D., Shashikanth, S. & Firdouse, A. (2004). Bioorg. Med. Chem. Lett. 12, 2093-2095.]); Naveen et al. (2006[Naveen, S., Khanum, S. A., Devaiah, V. T., Shashikanth, S., Anandalwar, S. M. & Prasad, S. (2006). Anal. Sci. 22, 183-184.]); Selvi et al. (2003[Selvi, A. T., Joseph, G. S. & Jayaprakasha, G. K. (2003). Food Microbiol. 20, 455-460.]). For a related structure, see: Mahendra et al. (2005[Mahendra, M., Khanum, S. A., Singh, A. K., Shashikanth, S., Doreswamy, B. H., Sridhar, M. A. & Shashidhara Prasad, J. (2005). Acta Cryst. E61, o2990-o2991.]).

[Scheme 1]

Experimental

Crystal data
  • C14H12O2

  • Mr = 212.24

  • Orthorhombic, P b c a

  • a = 7.7043 (4) Å

  • b = 16.3770 (8) Å

  • c = 17.7482 (9) Å

  • V = 2239.4 (2) Å3

  • Z = 8

  • Cu Kα radiation

  • μ = 0.67 mm−1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker X8 Proteum diffractometer

  • 7657 measured reflections

  • 1828 independent reflections

  • 1518 reflections with I > 2σ(I)

  • Rint = 0.037

Refinement
  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.129

  • S = 1.03

  • 1828 reflections

  • 147 parameters

  • H-atom parameters constrained

  • Δρmax = 0.14 e Å−3

  • Δρmin = −0.15 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O14—H14⋯O8i 0.82 1.91 2.7106 (19) 166
C2—H2⋯O14ii 0.93 2.57 3.448 (3) 158
Symmetry codes: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]; (ii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Benzophenone and related compounds have a wide variety of biological activities such as anti-fungal and anti-inflammatory (Khanum et al., 2004; Selvi et al., 2003). The presence of various substituents in the benzophenone nucleus is essential to determining the quantitative structure-activity relationships of these systems. The competence of benzophenones as chemotherapeutic agents, especially as inhibitors of HIV-1 reverse transcriptase RT, cancer and inflammation, is well established and their chemistry has been studied extensively. In addition, methyl-substituted benzophenones exhibit chemotherapeutical activity against fungi. Some studies were carried out to show that methyl-substituted benzophenones exhibit anti-fungal properties (Naveen et al., 2006). In view of its extensive background, the title compound was prepared and characterized by single-crystal X-ray diffraction.

In the molecular structure of the title compound (Fig. 1), bond lengths and angles do not show large deviations and are comparable with those reported for a similar structure (Mahendra et al., 2005). The dihedral angle between the two benzene rings (C1–C6) and (C9–C16) is 58.84 (12)°. The crystal structure is stabilized by intermolecular C—H···O and O—H···O hydrogen bonds (Table 1 & Fig. 2).

Related literature top

For the biological activity of benzophenone derivatives, see: Khanum et al. (2004); Naveen et al. (2006); Selvi et al. (2003). For bond-length and angle data in a related structure, see: Mahendra et al. (2005).

Experimental top

The title compound was synthesized by Fries rearrangement. 3-Methylphenylbenzoate was treated with anhydrous aluminium chloride (0.002 mol) as a catalyst at 150–170 °C under without solvent condition for about 2–3 h. Then the reaction mixture was cooled to room temperature and quenched with 6 N HCl in the presence of ice water. The reaction mixture was stirred for about 2–4 h, and the solid was filtered and recrystallized with acetonitrile to obtain the title compound.

Refinement top

All H-atoms were located in a difference map and then were positioned geometrically (C—H = 0.93–0.96 Å and O—H = 0.82 Å). They were refined using a riding model with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(O, Cmethyl) .

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. An ORTEP view of the molecule with the atom-labeling scheme. The thermal ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. A molecular packing view of the title compound down the a-axis, showing intermolecular interactions (dashed lines).
(4-Hydroxy-3-methylphenyl)(phenyl)methanone top
Crystal data top
C14H12O2F(000) = 896
Mr = 212.24Dx = 1.259 Mg m3
Orthorhombic, PbcaCu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ac 2abCell parameters from 1828 reflections
a = 7.7043 (4) Åθ = 5.0–64.4°
b = 16.3770 (8) ŵ = 0.67 mm1
c = 17.7482 (9) ÅT = 293 K
V = 2239.4 (2) Å3Block, colorless
Z = 80.30 × 0.25 × 0.20 mm
Data collection top
Bruker X8 Proteum
diffractometer
1518 reflections with I > 2σ(I)
Radiation source: Bruker MicroStar microfocus rotating anodeRint = 0.037
Helios multilayer optics monochromatorθmax = 64.4°, θmin = 5.0°
Detector resolution: 10.7 pixels mm-1h = 38
ϕ and ω scansk = 1818
7657 measured reflectionsl = 2020
1828 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.129 w = 1/[σ2(Fo2) + (0.0617P)2 + 0.8504P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
1828 reflectionsΔρmax = 0.14 e Å3
147 parametersΔρmin = 0.15 e Å3
0 restraintsExtinction correction: SHELXL, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0023 (3)
Crystal data top
C14H12O2V = 2239.4 (2) Å3
Mr = 212.24Z = 8
Orthorhombic, PbcaCu Kα radiation
a = 7.7043 (4) ŵ = 0.67 mm1
b = 16.3770 (8) ÅT = 293 K
c = 17.7482 (9) Å0.30 × 0.25 × 0.20 mm
Data collection top
Bruker X8 Proteum
diffractometer
1518 reflections with I > 2σ(I)
7657 measured reflectionsRint = 0.037
1828 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.129H-atom parameters constrained
S = 1.03Δρmax = 0.14 e Å3
1828 reflectionsΔρmin = 0.15 e Å3
147 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
O80.1870 (2)0.48369 (7)0.06235 (8)0.0564 (5)
O140.1579 (2)0.85740 (8)0.13455 (8)0.0637 (6)
C10.1850 (3)0.56879 (13)0.12119 (11)0.0553 (7)
C20.2200 (4)0.54665 (17)0.19461 (13)0.0756 (9)
C30.3252 (4)0.4804 (2)0.20900 (18)0.0944 (11)
C40.3942 (4)0.43527 (19)0.15054 (18)0.0886 (11)
C50.3563 (3)0.45538 (13)0.07775 (14)0.0623 (8)
C60.2522 (3)0.52263 (11)0.06186 (11)0.0457 (6)
C70.2081 (2)0.54037 (10)0.01775 (10)0.0407 (6)
C90.1909 (2)0.62549 (10)0.04420 (10)0.0374 (5)
C100.0890 (2)0.64224 (10)0.10733 (10)0.0385 (5)
C110.0763 (2)0.71935 (10)0.13776 (10)0.0412 (6)
C120.0375 (3)0.73782 (12)0.20447 (12)0.0624 (8)
C130.1725 (2)0.78203 (10)0.10381 (10)0.0426 (6)
C150.2755 (3)0.76672 (11)0.04110 (11)0.0456 (6)
C160.2830 (2)0.68939 (11)0.01104 (10)0.0431 (6)
H10.116700.614300.111200.0660*
H20.172800.576300.234300.0910*
H30.350000.466000.258500.1130*
H40.466500.391200.160800.1060*
H50.400300.423900.038500.0750*
H100.027500.599800.129700.0460*
H12A0.095500.688800.220300.0940*
H12B0.122100.778200.190700.0940*
H12C0.032500.758200.245100.0940*
H140.216400.889900.110200.0950*
H150.339400.808800.019400.0550*
H160.349900.679600.031600.0520*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O80.0647 (10)0.0356 (7)0.0688 (9)0.0039 (6)0.0086 (7)0.0147 (6)
O140.0935 (12)0.0353 (7)0.0622 (9)0.0083 (7)0.0170 (8)0.0035 (6)
C10.0597 (13)0.0525 (11)0.0538 (11)0.0129 (10)0.0040 (10)0.0005 (9)
C20.0883 (19)0.0862 (17)0.0524 (12)0.0340 (15)0.0057 (13)0.0043 (12)
C30.096 (2)0.111 (2)0.0763 (18)0.0373 (19)0.0327 (17)0.0442 (18)
C40.0747 (18)0.0860 (19)0.105 (2)0.0047 (15)0.0238 (17)0.0464 (18)
C50.0519 (13)0.0530 (12)0.0819 (15)0.0007 (10)0.0089 (12)0.0169 (11)
C60.0397 (10)0.0400 (10)0.0574 (11)0.0072 (8)0.0047 (9)0.0047 (8)
C70.0341 (10)0.0342 (9)0.0538 (10)0.0001 (7)0.0016 (8)0.0057 (8)
C90.0352 (9)0.0332 (9)0.0438 (9)0.0001 (7)0.0005 (7)0.0061 (7)
C100.0381 (10)0.0347 (9)0.0428 (9)0.0014 (7)0.0007 (8)0.0109 (7)
C110.0440 (11)0.0389 (9)0.0407 (9)0.0017 (7)0.0011 (8)0.0068 (7)
C120.0773 (16)0.0518 (12)0.0582 (12)0.0033 (11)0.0216 (11)0.0039 (10)
C130.0496 (11)0.0332 (9)0.0451 (10)0.0001 (8)0.0030 (8)0.0041 (7)
C150.0468 (11)0.0375 (10)0.0526 (10)0.0088 (8)0.0057 (9)0.0097 (8)
C160.0419 (11)0.0398 (9)0.0476 (10)0.0025 (8)0.0061 (8)0.0054 (8)
Geometric parameters (Å, º) top
O8—C71.231 (2)C11—C131.402 (2)
O14—C131.354 (2)C13—C151.390 (3)
O14—H140.8200C15—C161.375 (3)
C1—C61.396 (3)C1—H10.9300
C1—C21.379 (3)C2—H20.9300
C2—C31.378 (4)C3—H30.9300
C3—C41.380 (4)C4—H40.9300
C4—C51.365 (4)C5—H50.9300
C5—C61.391 (3)C10—H100.9300
C6—C71.482 (3)C12—H12A0.9600
C7—C91.477 (2)C12—H12B0.9600
C9—C161.395 (2)C12—H12C0.9600
C9—C101.395 (2)C15—H150.9300
C10—C111.377 (2)C16—H160.9300
C11—C121.504 (3)
O8···C6i3.385 (3)C13···H16vii2.8700
O8···C7i3.383 (2)C16···H12.8000
O8···C1i3.169 (3)H1···C92.8200
O8···O14ii2.7106 (19)H1···C162.8000
O14···O8iii2.7106 (19)H1···H162.5200
O8···H102.5600H2···O14viii2.5700
O8···H52.6200H3···C10ix3.0100
O8···H14ii1.9100H3···H10ix2.4500
O14···H12B2.7100H5···O82.6200
O14···H12C2.7200H5···C7v3.1000
O14···H2iv2.5700H10···O82.5600
C1···C163.159 (3)H10···H12A2.3700
C1···O8i3.169 (3)H10···H3vi2.4500
C5···C7v3.522 (3)H12A···H102.3700
C6···O8i3.385 (3)H12B···O142.7100
C7···C7i3.525 (2)H12C···O142.7200
C7···C5v3.522 (3)H14···H152.2900
C7···O8i3.383 (2)H14···O8iii1.9100
C16···C13.159 (3)H14···C7iii3.0200
C1···H162.7300H15···H142.2900
C6···H162.7300H15···C10x3.0700
C7···H14ii3.0200H16···C12.7300
C7···H5v3.1000H16···C62.7300
C9···H12.8200H16···H12.5200
C10···H3vi3.0100H16···C11x3.0500
C10···H15vii3.0700H16···C13x2.8700
C11···H16vii3.0500
C13—O14—H14109.00C9—C16—C15120.39 (17)
C2—C1—C6119.9 (2)C2—C1—H1120.00
C1—C2—C3119.8 (2)C6—C1—H1120.00
C2—C3—C4120.6 (3)C1—C2—H2120.00
C3—C4—C5120.0 (3)C3—C2—H2120.00
C4—C5—C6120.4 (2)C2—C3—H3120.00
C1—C6—C7121.87 (18)C4—C3—H3120.00
C5—C6—C7118.73 (18)C3—C4—H4120.00
C1—C6—C5119.32 (19)C5—C4—H4120.00
O8—C7—C9119.71 (16)C4—C5—H5120.00
C6—C7—C9120.58 (15)C6—C5—H5120.00
O8—C7—C6119.71 (15)C9—C10—H10119.00
C7—C9—C10119.43 (15)C11—C10—H10119.00
C7—C9—C16121.90 (15)C11—C12—H12A109.00
C10—C9—C16118.53 (15)C11—C12—H12B110.00
C9—C10—C11122.36 (15)C11—C12—H12C109.00
C10—C11—C12122.32 (15)H12A—C12—H12B110.00
C12—C11—C13119.95 (15)H12A—C12—H12C109.00
C10—C11—C13117.73 (15)H12B—C12—H12C109.00
O14—C13—C11116.76 (15)C13—C15—H15120.00
O14—C13—C15122.31 (15)C16—C15—H15120.00
C11—C13—C15120.92 (16)C9—C16—H16120.00
C13—C15—C16120.05 (17)C15—C16—H16120.00
C6—C1—C2—C31.8 (4)C6—C7—C9—C1628.8 (2)
C2—C1—C6—C51.0 (3)C7—C9—C10—C11175.79 (15)
C2—C1—C6—C7175.6 (2)C16—C9—C10—C110.1 (3)
C1—C2—C3—C40.8 (5)C7—C9—C16—C15174.39 (17)
C2—C3—C4—C51.0 (5)C10—C9—C16—C151.2 (3)
C3—C4—C5—C61.8 (4)C9—C10—C11—C12178.23 (17)
C4—C5—C6—C10.8 (3)C9—C10—C11—C131.0 (2)
C4—C5—C6—C7177.5 (2)C10—C11—C13—O14179.90 (15)
C1—C6—C7—O8142.2 (2)C10—C11—C13—C150.7 (3)
C1—C6—C7—C938.4 (3)C12—C11—C13—O140.7 (2)
C5—C6—C7—O834.4 (3)C12—C11—C13—C15178.57 (18)
C5—C6—C7—C9145.05 (18)O14—C13—C15—C16178.60 (17)
O8—C7—C9—C1024.9 (2)C11—C13—C15—C160.6 (3)
O8—C7—C9—C16150.64 (17)C13—C15—C16—C91.5 (3)
C6—C7—C9—C10155.66 (17)
Symmetry codes: (i) x, y+1, z; (ii) x+1/2, y1/2, z; (iii) x+1/2, y+1/2, z; (iv) x, y+3/2, z+1/2; (v) x+1, y+1, z; (vi) x+1/2, y+1, z+1/2; (vii) x1/2, y+3/2, z; (viii) x, y+3/2, z1/2; (ix) x+1/2, y+1, z1/2; (x) x+1/2, y+3/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O14—H14···O8iii0.821.912.7106 (19)166
C2—H2···O14viii0.932.573.448 (3)158
Symmetry codes: (iii) x+1/2, y+1/2, z; (viii) x, y+3/2, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O14—H14···O8i0.821.912.7106 (19)166
C2—H2···O14ii0.932.573.448 (3)158
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x, y+3/2, z1/2.
 

Acknowledgements

The authors would like to thank the University of Mysore for providing the diffractometer facility under IoE. VLR acknowledges the financial support provided by the Department of Science and Technology, New Delhi, under the INSPIRE-Fellowship scheme [IF110555]. SAK gratefully acknowledges the financial assistance provided by the UGC under the major research project scheme [F.39/737/2010 (SR)]. CSD would like to thank the University of Mysore for the award of an RFSMS fellowship under the head DV5/Physics/389/RFSMS/2009–2010/10.07.2012.

References

First citationBruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationKhanum, S. A., Venu, T. D., Shashikanth, S. & Firdouse, A. (2004). Bioorg. Med. Chem. Lett. 12, 2093–2095.
First citationMahendra, M., Khanum, S. A., Singh, A. K., Shashikanth, S., Doreswamy, B. H., Sridhar, M. A. & Shashidhara Prasad, J. (2005). Acta Cryst. E61, o2990–o2991.  Web of Science CSD CrossRef CAS IUCr Journals
First citationNaveen, S., Khanum, S. A., Devaiah, V. T., Shashikanth, S., Anandalwar, S. M. & Prasad, S. (2006). Anal. Sci. 22, 183–184.  Web of Science PubMed
First citationSelvi, A. T., Joseph, G. S. & Jayaprakasha, G. K. (2003). Food Microbiol. 20, 455–460.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals

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