(4-Hy­droxy-3,5-di­methyl­phen­yl)(phen­yl)methanone

Dileep, C.S.; Prashanth, T.; Jeyaseelan, S.; Khanum, S.A.; Sridhar, M.A.

doi:10.1107/S1600536813028444

organic compounds

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ISSN: 2056-9890

Volume 69| Part 11| November 2013| Page o1676

doi:10.1107/S1600536813028444

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(4-Hydroxy-3,5-dimethylphenyl)(phenyl)methanone

C. S. Dileep,^a T. Prashanth,^b S. Jeyaseelan,^c S. A. Khanum ^b and M. A. Sridhar ^a ^*

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

(Received 6 September 2013; accepted 16 October 2013; online 19 October 2013)

In the molecule of the title compound, C₁₅H₁₄O₂, the dihedral angle between the benzene and phenyl rings is 61.27 (8)°. In the crystal, O—H⋯O and weak C—H⋯O hydrogen bonds link the molecules into chains extending along the c-axis direction.

CCDC reference: 966719

Related literature

For the biological activity of benzophenone derivatives, see: Naldoni et al. (2009 ); Naveen et al. (2006 ); Selvi et al. (2003 ). For bond-length and angle data in a related structure, see: Mahendra et al. (2005 ).

Experimental

Crystal data

C₁₅H₁₄O₂
M_r = 226.26
Monoclinic, P 2₁ /c
a = 4.7741 (13) Å
b = 15.198 (4) Å
c = 17.274 (5) Å
β = 95.275 (12)°
V = 1248.0 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
2238 measured reflections
2238 independent reflections
1777 reflections with I > 2σ(I)

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.140
S = 1.02
2238 reflections
157 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O11ⁱ	0.82	2.03	2.7528 (17)	147
C13—H13⋯O5ⁱⁱ	0.93	2.55	3.301 (2)	138
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); 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: 966719

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813028444/zs2279sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813028444/zs2279Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813028444/zs2279Isup3.cml

checkCIF report

Comment top

Benzophenone and its derivatives show various biological activities such as anti-fungal and anti-inflamatory (Naldoni et al., 2009 and Selvi et al., 2003). The presence of various substituents in the benzophenone nucleus is essential in determining the quantitative structure-activity relationships for 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 these compounds exhibit anti-fungal properties (Naveen et al., 2006) In view of its extensive background, the title compound, C₁₅H₁₄O₂, was prepared and characterized by single-crystal X-ray diffraction and the structure is reported herein.

In the molecular structure of this compound (Fig. 1), bond lengths and angles do not show large deviations from and are comparable with those reported for a similar structure (Mahendra et al., 2005). The dihedral angle between the two benzene rings is 61.27 (8)°. The crystal structure is stabilized by intermolecular O—H···O and weak C—H···O hydrogen bonds, forming one-dimensional chains extending along the c axis in the unit cell (Fig. 2).

Related literature top

For the biological activity of benzophenone derivatives, see: Naldoni et al. (2009); 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

(4-Hydroxy-3,5-dimethyl-phenyl)phenyl-methanone was synthesized by the Fries rearrangement. 2,6-Dimethylphenyl benzoate (0.022 mol) was mixed with anhydrous aluminium chloride (0.044 mol) and fused at 150–170 °C under dry conditions for about 2–3 h. The reaction mixture was then cooled to room temperature and quenched with 6 M HCl in the presence of ice water. The reaction mixture was stirred for about 2–3 h, then filtered and the product was recrystallized from ethanol to obtain colourless crystals.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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. Molecular conformation and atom numbering scheme for the title compound, showing 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the molecule in the unit cell viewed down the a axis.

(4-Hydroxy-3,5-dimethylphenyl)(phenyl)methanone top

Crystal data top

C₁₅H₁₄O₂	F(000) = 480
M_r = 226.26	D_x = 1.204 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2238 reflections
a = 4.7741 (13) Å	θ = 1.8–25.3°
b = 15.198 (4) Å	µ = 0.08 mm⁻¹
c = 17.274 (5) Å	T = 293 K
β = 95.275 (12)°	Block, colorless
V = 1248.0 (6) Å³	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	1777 reflections with I > 2σ(I)
Radiation source: fine focus sealed tube	R_int = 0.000
Graphite monochromator	θ_max = 25.3°, θ_min = 1.8°
ω and ϕ scans	h = −5→5
2238 measured reflections	k = 0→18
2238 independent reflections	l = 0→20

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)] = 0.041	H-atom parameters constrained
wR(F²) = 0.140	w = 1/[σ²(F_o²) + (0.0867P)² + 0.1512P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.011
2238 reflections	Δρ_max = 0.15 e Å⁻³
157 parameters	Δρ_min = −0.13 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), FC^*=KFC[1+0.001XFC²Λ³/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.020 (6)

Crystal data top

C₁₅H₁₄O₂	V = 1248.0 (6) Å³
M_r = 226.26	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 4.7741 (13) Å	µ = 0.08 mm⁻¹
b = 15.198 (4) Å	T = 293 K
c = 17.274 (5) Å	0.30 × 0.25 × 0.20 mm
β = 95.275 (12)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	1777 reflections with I > 2σ(I)
2238 measured reflections	R_int = 0.000
2238 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 1.02	Δρ_max = 0.15 e Å⁻³
2238 reflections	Δρ_min = −0.13 e Å⁻³
157 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 esds 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 > 2sigma(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
O5	0.0022 (3)	0.17634 (8)	0.08784 (6)	0.0634 (4)
O11	−0.1206 (3)	0.26574 (7)	−0.26812 (6)	0.0637 (5)
C1	−0.2554 (3)	0.31934 (9)	−0.07292 (8)	0.0450 (5)
C2	−0.2212 (3)	0.28659 (10)	0.00211 (8)	0.0454 (5)
C3	−0.3756 (4)	0.32668 (13)	0.06525 (9)	0.0641 (6)
C4	−0.0447 (3)	0.21413 (10)	0.01672 (8)	0.0454 (5)
C6	0.0962 (3)	0.17493 (10)	−0.04227 (8)	0.0466 (5)
C7	0.2852 (4)	0.09705 (12)	−0.02409 (11)	0.0663 (7)
C8	0.0532 (3)	0.20949 (10)	−0.11568 (8)	0.0463 (5)
C9	−0.1201 (3)	0.28197 (9)	−0.13271 (8)	0.0430 (5)
C10	−0.1712 (3)	0.31344 (9)	−0.21370 (8)	0.0458 (5)
C12	−0.2919 (3)	0.40255 (9)	−0.22965 (8)	0.0440 (5)
C13	−0.5127 (4)	0.41181 (11)	−0.28726 (9)	0.0551 (6)
C14	−0.6304 (4)	0.49312 (14)	−0.30321 (11)	0.0692 (7)
C15	−0.5237 (5)	0.56614 (12)	−0.26413 (11)	0.0684 (7)
C16	−0.3009 (4)	0.55860 (11)	−0.20861 (11)	0.0634 (6)
C17	−0.1870 (4)	0.47666 (10)	−0.19002 (9)	0.0535 (5)
H1	−0.37210	0.36770	−0.08360	0.0540*
H3A	−0.49780	0.37240	0.04370	0.0960*
H3B	−0.24260	0.35110	0.10450	0.0960*
H3C	−0.48500	0.28220	0.08800	0.0960*
H5	−0.08640	0.20290	0.11900	0.0950*
H7A	0.17730	0.04930	−0.00590	0.0990*
H7B	0.43120	0.11290	0.01540	0.0990*
H7C	0.36800	0.07920	−0.07020	0.0990*
H8	0.14290	0.18370	−0.15550	0.0560*
H13	−0.58120	0.36280	−0.31520	0.0660*
H14	−0.78260	0.49860	−0.34060	0.0830*
H15	−0.60310	0.62110	−0.27540	0.0820*
H16	−0.22610	0.60850	−0.18340	0.0760*
H17	−0.04030	0.47130	−0.15100	0.0640*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O5	0.0797 (8)	0.0818 (8)	0.0287 (6)	0.0183 (6)	0.0057 (5)	0.0122 (5)
O11	0.1119 (10)	0.0537 (7)	0.0258 (6)	0.0055 (6)	0.0085 (6)	−0.0042 (5)
C1	0.0549 (9)	0.0495 (8)	0.0305 (8)	0.0022 (6)	0.0031 (6)	0.0003 (6)
C2	0.0523 (9)	0.0571 (9)	0.0270 (8)	−0.0006 (7)	0.0049 (6)	−0.0013 (6)
C3	0.0787 (12)	0.0819 (12)	0.0333 (9)	0.0148 (9)	0.0137 (8)	0.0005 (8)
C4	0.0524 (9)	0.0586 (9)	0.0246 (7)	−0.0031 (7)	−0.0004 (6)	0.0037 (6)
C6	0.0520 (9)	0.0545 (8)	0.0330 (8)	0.0007 (6)	0.0016 (6)	0.0001 (6)
C7	0.0764 (12)	0.0698 (11)	0.0525 (11)	0.0179 (9)	0.0048 (9)	0.0067 (8)
C8	0.0570 (9)	0.0526 (8)	0.0302 (8)	0.0004 (7)	0.0091 (7)	−0.0040 (6)
C9	0.0565 (9)	0.0474 (8)	0.0248 (7)	−0.0036 (6)	0.0027 (6)	−0.0009 (6)
C10	0.0627 (10)	0.0481 (8)	0.0269 (8)	−0.0086 (7)	0.0057 (6)	−0.0029 (6)
C12	0.0586 (9)	0.0497 (8)	0.0244 (7)	−0.0060 (6)	0.0078 (6)	0.0018 (6)
C13	0.0649 (10)	0.0651 (10)	0.0351 (9)	−0.0031 (8)	0.0036 (8)	0.0004 (7)
C14	0.0708 (12)	0.0884 (14)	0.0481 (10)	0.0165 (10)	0.0036 (9)	0.0103 (9)
C15	0.0848 (13)	0.0628 (11)	0.0610 (12)	0.0199 (9)	0.0259 (10)	0.0163 (9)
C16	0.0850 (13)	0.0479 (9)	0.0605 (11)	−0.0057 (8)	0.0247 (10)	−0.0041 (8)
C17	0.0649 (10)	0.0534 (9)	0.0423 (9)	−0.0055 (7)	0.0050 (7)	−0.0025 (7)

Geometric parameters (Å, º) top

O5—C4	1.3560 (18)	C14—C15	1.372 (3)
O11—C10	1.2286 (18)	C15—C16	1.370 (3)
O5—H5	0.8200	C16—C17	1.385 (2)
C1—C2	1.384 (2)	C1—H1	0.9300
C1—C9	1.389 (2)	C3—H3A	0.9600
C2—C4	1.396 (2)	C3—H3B	0.9600
C2—C3	1.501 (2)	C3—H3C	0.9600
C4—C6	1.404 (2)	C7—H7A	0.9600
C6—C7	1.504 (2)	C7—H7B	0.9600
C6—C8	1.371 (2)	C7—H7C	0.9600
C8—C9	1.393 (2)	C8—H8	0.9300
C9—C10	1.477 (2)	C13—H13	0.9300
C10—C12	1.488 (2)	C14—H14	0.9300
C12—C17	1.387 (2)	C15—H15	0.9300
C12—C13	1.389 (2)	C16—H16	0.9300
C13—C14	1.375 (3)	C17—H17	0.9300

C4—O5—H5	109.00	C2—C1—H1	119.00
C2—C1—C9	121.76 (13)	C9—C1—H1	119.00
C1—C2—C3	120.74 (14)	C2—C3—H3A	109.00
C1—C2—C4	118.07 (13)	C2—C3—H3B	109.00
C3—C2—C4	121.18 (13)	C2—C3—H3C	109.00
O5—C4—C6	115.31 (13)	H3A—C3—H3B	109.00
C2—C4—C6	121.68 (13)	H3A—C3—H3C	110.00
O5—C4—C2	123.01 (13)	H3B—C3—H3C	109.00
C4—C6—C8	117.90 (14)	C6—C7—H7A	110.00
C7—C6—C8	122.06 (14)	C6—C7—H7B	109.00
C4—C6—C7	120.04 (13)	C6—C7—H7C	110.00
C6—C8—C9	122.28 (13)	H7A—C7—H7B	109.00
C1—C9—C10	121.61 (13)	H7A—C7—H7C	109.00
C8—C9—C10	119.95 (12)	H7B—C7—H7C	109.00
C1—C9—C8	118.31 (13)	C6—C8—H8	119.00
O11—C10—C9	120.44 (13)	C9—C8—H8	119.00
C9—C10—C12	119.84 (12)	C12—C13—H13	120.00
O11—C10—C12	119.71 (13)	C14—C13—H13	120.00
C10—C12—C13	118.72 (13)	C13—C14—H14	120.00
C13—C12—C17	119.15 (14)	C15—C14—H14	120.00
C10—C12—C17	122.11 (13)	C14—C15—H15	120.00
C12—C13—C14	120.27 (16)	C16—C15—H15	120.00
C13—C14—C15	120.12 (18)	C15—C16—H16	120.00
C14—C15—C16	120.39 (18)	C17—C16—H16	120.00
C15—C16—C17	120.04 (16)	C12—C17—H17	120.00
C12—C17—C16	119.96 (16)	C16—C17—H17	120.00

C9—C1—C2—C3	−178.40 (15)	C1—C9—C10—O11	−158.32 (15)
C9—C1—C2—C4	0.1 (2)	C1—C9—C10—C12	20.0 (2)
C2—C1—C9—C8	0.2 (2)	C8—C9—C10—O11	17.4 (2)
C2—C1—C9—C10	176.00 (13)	C8—C9—C10—C12	−164.22 (13)
C1—C2—C4—O5	−179.48 (14)	O11—C10—C12—C13	45.2 (2)
C1—C2—C4—C6	0.2 (2)	O11—C10—C12—C17	−133.42 (17)
C3—C2—C4—O5	−1.0 (2)	C9—C10—C12—C13	−133.19 (15)
C3—C2—C4—C6	178.64 (15)	C9—C10—C12—C17	48.2 (2)
O5—C4—C6—C7	−0.5 (2)	C10—C12—C13—C14	179.61 (15)
O5—C4—C6—C8	178.98 (14)	C17—C12—C13—C14	−1.8 (2)
C2—C4—C6—C7	179.84 (15)	C10—C12—C17—C16	178.02 (15)
C2—C4—C6—C8	−0.7 (2)	C13—C12—C17—C16	−0.6 (2)
C4—C6—C8—C9	1.0 (2)	C12—C13—C14—C15	2.3 (3)
C7—C6—C8—C9	−179.55 (15)	C13—C14—C15—C16	−0.5 (3)
C6—C8—C9—C1	−0.7 (2)	C14—C15—C16—C17	−1.8 (3)
C6—C8—C9—C10	−176.64 (14)	C15—C16—C17—C12	2.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O11ⁱ	0.82	2.03	2.7528 (17)	147
C13—H13···O5ⁱⁱ	0.93	2.55	3.301 (2)	138

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O11ⁱ	0.82	2.03	2.7528 (17)	147
C13—H13···O5ⁱⁱ	0.93	2.55	3.301 (2)	138

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

Acknowledgements

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. The authors SAK and TP acknowledge the financial support provided by the UGC, New Delhi, under the Major Research Project Scheme No. F.39/737/2010 (SR).

References

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