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

Dileep, C.S.; Lakshmi Ranganatha, V.; Lokanath, N.K.; Shaukath, A.K.; Sridhar, M.A.

doi:10.1107/S160053681302521X

organic compounds

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ISSN: 2056-9890

Volume 69| Part 10| October 2013| Page o1550

doi:10.1107/S160053681302521X

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

C. S. Dileep,^a V. Lakshmi Ranganatha,^b N. K. Lokanath,^a A. K. Shaukath ^b and M. A. Sridhar ^a ^*

^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.

CCDC reference: 960686

Related literature

For the biological activity of benzophenone derivatives, see: Khanum et al. (2004 ); Naveen et al. (2006 ); Selvi et al. (2003 ). For a related structure, see: Mahendra et al. (2005 ).

Experimental

Crystal data

C₁₄H₁₂O₂
M_r = 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)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.129
S = 1.03
1828 reflections
147 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; 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.

Supporting information

CCDC reference: 960686

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681302521X/is5303sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681302521X/is5303Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681302521X/is5303Isup3.cml

checkCIF report

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.

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

	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.
	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

C₁₄H₁₂O₂	F(000) = 896
M_r = 212.24	D_x = 1.259 Mg m⁻³
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1828 reflections
a = 7.7043 (4) Å	θ = 5.0–64.4°
b = 16.3770 (8) Å	µ = 0.67 mm⁻¹
c = 17.7482 (9) Å	T = 293 K
V = 2239.4 (2) Å³	Block, colorless
Z = 8	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker X8 Proteum diffractometer	1518 reflections with I > 2σ(I)
Radiation source: Bruker MicroStar microfocus rotating anode	R_int = 0.037
Helios multilayer optics monochromator	θ_max = 64.4°, θ_min = 5.0°
Detector resolution: 10.7 pixels mm^-1	h = −3→8
ϕ and ω scans	k = −18→18
7657 measured reflections	l = −20→20
1828 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.129	w = 1/[σ²(F_o²) + (0.0617P)² + 0.8504P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
1828 reflections	Δρ_max = 0.14 e Å⁻³
147 parameters	Δρ_min = −0.15 e Å⁻³
0 restraints	Extinction correction: SHELXL, FC^*=KFC[1+0.001XFC²Λ³/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0023 (3)

Crystal data top

C₁₄H₁₂O₂	V = 2239.4 (2) Å³
M_r = 212.24	Z = 8
Orthorhombic, Pbca	Cu Kα radiation
a = 7.7043 (4) Å	µ = 0.67 mm⁻¹
b = 16.3770 (8) Å	T = 293 K
c = 17.7482 (9) Å	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker X8 Proteum diffractometer	1518 reflections with I > 2σ(I)
7657 measured reflections	R_int = 0.037
1828 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.03	Δρ_max = 0.14 e Å⁻³
1828 reflections	Δρ_min = −0.15 e Å⁻³
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

	x	y	z	U_iso*/U_eq
O8	0.1870 (2)	0.48369 (7)	0.06235 (8)	0.0564 (5)
O14	0.1579 (2)	0.85740 (8)	0.13455 (8)	0.0637 (6)
C1	0.1850 (3)	0.56879 (13)	−0.12119 (11)	0.0553 (7)
C2	0.2200 (4)	0.54665 (17)	−0.19461 (13)	0.0756 (9)
C3	0.3252 (4)	0.4804 (2)	−0.20900 (18)	0.0944 (11)
C4	0.3942 (4)	0.43527 (19)	−0.15054 (18)	0.0886 (11)
C5	0.3563 (3)	0.45538 (13)	−0.07775 (14)	0.0623 (8)
C6	0.2522 (3)	0.52263 (11)	−0.06186 (11)	0.0457 (6)
C7	0.2081 (2)	0.54037 (10)	0.01775 (10)	0.0407 (6)
C9	0.1909 (2)	0.62549 (10)	0.04420 (10)	0.0374 (5)
C10	0.0890 (2)	0.64224 (10)	0.10733 (10)	0.0385 (5)
C11	0.0763 (2)	0.71935 (10)	0.13776 (10)	0.0412 (6)
C12	−0.0375 (3)	0.73782 (12)	0.20447 (12)	0.0624 (8)
C13	0.1725 (2)	0.78203 (10)	0.10381 (10)	0.0426 (6)
C15	0.2755 (3)	0.76672 (11)	0.04110 (11)	0.0456 (6)
C16	0.2830 (2)	0.68939 (11)	0.01104 (10)	0.0431 (6)
H1	0.11670	0.61430	−0.11120	0.0660*
H2	0.17280	0.57630	−0.23430	0.0910*
H3	0.35000	0.46600	−0.25850	0.1130*
H4	0.46650	0.39120	−0.16080	0.1060*
H5	0.40030	0.42390	−0.03850	0.0750*
H10	0.02750	0.59980	0.12970	0.0460*
H12A	−0.09550	0.68880	0.22030	0.0940*
H12B	−0.12210	0.77820	0.19070	0.0940*
H12C	0.03250	0.75820	0.24510	0.0940*
H14	0.21640	0.88990	0.11020	0.0950*
H15	0.33940	0.80880	0.01940	0.0550*
H16	0.34990	0.67960	−0.03160	0.0520*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O8	0.0647 (10)	0.0356 (7)	0.0688 (9)	0.0039 (6)	0.0086 (7)	0.0147 (6)
O14	0.0935 (12)	0.0353 (7)	0.0622 (9)	−0.0083 (7)	0.0170 (8)	−0.0035 (6)
C1	0.0597 (13)	0.0525 (11)	0.0538 (11)	−0.0129 (10)	0.0040 (10)	0.0005 (9)
C2	0.0883 (19)	0.0862 (17)	0.0524 (12)	−0.0340 (15)	0.0057 (13)	−0.0043 (12)
C3	0.096 (2)	0.111 (2)	0.0763 (18)	−0.0373 (19)	0.0327 (17)	−0.0442 (18)
C4	0.0747 (18)	0.0860 (19)	0.105 (2)	−0.0047 (15)	0.0238 (17)	−0.0464 (18)
C5	0.0519 (13)	0.0530 (12)	0.0819 (15)	−0.0007 (10)	0.0089 (12)	−0.0169 (11)
C6	0.0397 (10)	0.0400 (10)	0.0574 (11)	−0.0072 (8)	0.0047 (9)	−0.0047 (8)
C7	0.0341 (10)	0.0342 (9)	0.0538 (10)	−0.0001 (7)	0.0016 (8)	0.0057 (8)
C9	0.0352 (9)	0.0332 (9)	0.0438 (9)	−0.0001 (7)	−0.0005 (7)	0.0061 (7)
C10	0.0381 (10)	0.0347 (9)	0.0428 (9)	−0.0014 (7)	0.0007 (8)	0.0109 (7)
C11	0.0440 (11)	0.0389 (9)	0.0407 (9)	0.0017 (7)	0.0011 (8)	0.0068 (7)
C12	0.0773 (16)	0.0518 (12)	0.0582 (12)	0.0033 (11)	0.0216 (11)	0.0039 (10)
C13	0.0496 (11)	0.0332 (9)	0.0451 (10)	0.0001 (8)	−0.0030 (8)	0.0041 (7)
C15	0.0468 (11)	0.0375 (10)	0.0526 (10)	−0.0088 (8)	0.0057 (9)	0.0097 (8)
C16	0.0419 (11)	0.0398 (9)	0.0476 (10)	−0.0025 (8)	0.0061 (8)	0.0054 (8)

Geometric parameters (Å, º) top

O8—C7	1.231 (2)	C11—C13	1.402 (2)
O14—C13	1.354 (2)	C13—C15	1.390 (3)
O14—H14	0.8200	C15—C16	1.375 (3)
C1—C6	1.396 (3)	C1—H1	0.9300
C1—C2	1.379 (3)	C2—H2	0.9300
C2—C3	1.378 (4)	C3—H3	0.9300
C3—C4	1.380 (4)	C4—H4	0.9300
C4—C5	1.365 (4)	C5—H5	0.9300
C5—C6	1.391 (3)	C10—H10	0.9300
C6—C7	1.482 (3)	C12—H12A	0.9600
C7—C9	1.477 (2)	C12—H12B	0.9600
C9—C16	1.395 (2)	C12—H12C	0.9600
C9—C10	1.395 (2)	C15—H15	0.9300
C10—C11	1.377 (2)	C16—H16	0.9300
C11—C12	1.504 (3)

O8···C6ⁱ	3.385 (3)	C13···H16^vii	2.8700
O8···C7ⁱ	3.383 (2)	C16···H1	2.8000
O8···C1ⁱ	3.169 (3)	H1···C9	2.8200
O8···O14ⁱⁱ	2.7106 (19)	H1···C16	2.8000
O14···O8ⁱⁱⁱ	2.7106 (19)	H1···H16	2.5200
O8···H10	2.5600	H2···O14^viii	2.5700
O8···H5	2.6200	H3···C10^ix	3.0100
O8···H14ⁱⁱ	1.9100	H3···H10^ix	2.4500
O14···H12B	2.7100	H5···O8	2.6200
O14···H12C	2.7200	H5···C7^v	3.1000
O14···H2^iv	2.5700	H10···O8	2.5600
C1···C16	3.159 (3)	H10···H12A	2.3700
C1···O8ⁱ	3.169 (3)	H10···H3^vi	2.4500
C5···C7^v	3.522 (3)	H12A···H10	2.3700
C6···O8ⁱ	3.385 (3)	H12B···O14	2.7100
C7···C7ⁱ	3.525 (2)	H12C···O14	2.7200
C7···C5^v	3.522 (3)	H14···H15	2.2900
C7···O8ⁱ	3.383 (2)	H14···O8ⁱⁱⁱ	1.9100
C16···C1	3.159 (3)	H14···C7ⁱⁱⁱ	3.0200
C1···H16	2.7300	H15···H14	2.2900
C6···H16	2.7300	H15···C10^x	3.0700
C7···H14ⁱⁱ	3.0200	H16···C1	2.7300
C7···H5^v	3.1000	H16···C6	2.7300
C9···H1	2.8200	H16···H1	2.5200
C10···H3^vi	3.0100	H16···C11^x	3.0500
C10···H15^vii	3.0700	H16···C13^x	2.8700
C11···H16^vii	3.0500

C13—O14—H14	109.00	C9—C16—C15	120.39 (17)
C2—C1—C6	119.9 (2)	C2—C1—H1	120.00
C1—C2—C3	119.8 (2)	C6—C1—H1	120.00
C2—C3—C4	120.6 (3)	C1—C2—H2	120.00
C3—C4—C5	120.0 (3)	C3—C2—H2	120.00
C4—C5—C6	120.4 (2)	C2—C3—H3	120.00
C1—C6—C7	121.87 (18)	C4—C3—H3	120.00
C5—C6—C7	118.73 (18)	C3—C4—H4	120.00
C1—C6—C5	119.32 (19)	C5—C4—H4	120.00
O8—C7—C9	119.71 (16)	C4—C5—H5	120.00
C6—C7—C9	120.58 (15)	C6—C5—H5	120.00
O8—C7—C6	119.71 (15)	C9—C10—H10	119.00
C7—C9—C10	119.43 (15)	C11—C10—H10	119.00
C7—C9—C16	121.90 (15)	C11—C12—H12A	109.00
C10—C9—C16	118.53 (15)	C11—C12—H12B	110.00
C9—C10—C11	122.36 (15)	C11—C12—H12C	109.00
C10—C11—C12	122.32 (15)	H12A—C12—H12B	110.00
C12—C11—C13	119.95 (15)	H12A—C12—H12C	109.00
C10—C11—C13	117.73 (15)	H12B—C12—H12C	109.00
O14—C13—C11	116.76 (15)	C13—C15—H15	120.00
O14—C13—C15	122.31 (15)	C16—C15—H15	120.00
C11—C13—C15	120.92 (16)	C9—C16—H16	120.00
C13—C15—C16	120.05 (17)	C15—C16—H16	120.00

C6—C1—C2—C3	−1.8 (4)	C6—C7—C9—C16	−28.8 (2)
C2—C1—C6—C5	1.0 (3)	C7—C9—C10—C11	175.79 (15)
C2—C1—C6—C7	−175.6 (2)	C16—C9—C10—C11	0.1 (3)
C1—C2—C3—C4	0.8 (5)	C7—C9—C16—C15	−174.39 (17)
C2—C3—C4—C5	1.0 (5)	C10—C9—C16—C15	1.2 (3)
C3—C4—C5—C6	−1.8 (4)	C9—C10—C11—C12	178.23 (17)
C4—C5—C6—C1	0.8 (3)	C9—C10—C11—C13	−1.0 (2)
C4—C5—C6—C7	177.5 (2)	C10—C11—C13—O14	179.90 (15)
C1—C6—C7—O8	142.2 (2)	C10—C11—C13—C15	0.7 (3)
C1—C6—C7—C9	−38.4 (3)	C12—C11—C13—O14	0.7 (2)
C5—C6—C7—O8	−34.4 (3)	C12—C11—C13—C15	−178.57 (18)
C5—C6—C7—C9	145.05 (18)	O14—C13—C15—C16	−178.60 (17)
O8—C7—C9—C10	−24.9 (2)	C11—C13—C15—C16	0.6 (3)
O8—C7—C9—C16	150.64 (17)	C13—C15—C16—C9	−1.5 (3)
C6—C7—C9—C10	155.66 (17)

Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1/2, y−1/2, 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) x−1/2, −y+3/2, −z; (viii) x, −y+3/2, z−1/2; (ix) −x+1/2, −y+1, z−1/2; (x) x+1/2, −y+3/2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O14—H14···O8ⁱⁱⁱ	0.82	1.91	2.7106 (19)	166
C2—H2···O14^viii	0.93	2.57	3.448 (3)	158

Symmetry codes: (iii) −x+1/2, y+1/2, z; (viii) x, −y+3/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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+1/2, y+1/2, z; (ii) x, −y+3/2, z−1/2.

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.

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