(4-Fluoro­phen­yl)(4-hy­droxy-3-methyl­phen­yl)methanone

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

doi:10.1107/S1600536813033783

organic compounds

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ISSN: 2056-9890

Volume 70| Part 1| January 2014| Page o76

https://doi.org/10.1107/S1600536813033783

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(4-Fluorophenyl)(4-hydroxy-3-methylphenyl)methanone

C. S. Dileep,^a V. Lakshmi Ranganatha,^b N. K. Lokanath,^a S. A. Khanum ^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 10 December 2013; accepted 13 December 2013; online 21 December 2013)

In the title compound, C₁₄H₁₁FO₂, the two benzene rings are not coplanar, with a dihedral angle of 57.45 (12)° between their planes. In the crystal, molecules are linked by an O—H⋯O hydrogen bond, forming a 2₁ helical chain along the b axis.

CCDC reference: 976942

Related literature

For the biological activities of benzophenone derivatives, see: Khanum et al. (2004 ); Naveen et al. (2006 ); Selvi et al. (2003 ). For related structures, see: Mahendra et al. (2005 ); Dileep, Lakshmi Ranganatha et al. (2013 ); Dileep, Prashanth et al. (2013 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₄H₁₁FO₂
M_r = 230.23
Monoclinic, P 2₁ /n
a = 5.9265 (10) Å
b = 13.112 (2) Å
c = 14.556 (2) Å
β = 96.875 (7)°
V = 1123.0 (3) Å³
Z = 4
Cu Kα radiation
μ = 0.85 mm⁻¹
T = 296 K
0.27 × 0.25 × 0.23 mm

Data collection

Bruker X8 Proteum diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.804, T_max = 0.829
7047 measured reflections
1769 independent reflections
1317 reflections with I > 2σ(I)
R_int = 0.065

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.273
S = 1.16
1769 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O14—H14⋯O9ⁱ	0.82	1.91	2.688 (3)	158
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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: Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 976942

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813033783/is5325sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813033783/is5325Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813033783/is5325Isup3.cml

checkCIF report

Comment top

The great interest in the benzophenone substances is fundamentally due to their diverse biological and chemical properties. Benzophenone and related compounds have a wide variety of biological activities such as anti-fungal and anti-inflammatory activities (Khanum et al., 2004; Selvi et al., 2003). The presence of various substituents in the benzophenone nucleus is essential in 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. 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; Dileep, Lakshmi Ranganatha et al., 2013; Dileep, Prashanth et al., 2013). The mean plane angle between the two phenyl rings (C2–C7) and (C10–C13/C15/C17) is 57.45 (12)°. The bond length between C2 and F1 is 1.357 (4) Å and is normal with the standard value (Allen et al., 1987). The conformation of the attachment of the two phenyl rings to the central carbonyl group can also be characterized by torsion angles (O9—C8—C5—C6) and (O9—C8—C10—C17) of -141.1 (3) and -152.8 (3)°, respectively. The crystal structure is stabilized by intermolecular O—H···O hydrogen bonds. The molecular packing when viewed down the a axis is shown in Fig. 2.

Related literature top

For the biological activities of benzophenone derivatives, see: Khanum et al. (2004); Naveen et al. (2006); Selvi et al. (2003). For related structures, see: Mahendra et al. (2005); Dileep, Lakshmi Ranganatha et al. (2013); Dileep, Prashanth et al. (2013). For organic bond-length data, see: Allen et al. (12987).

Experimental top

The title compound was synthesized by a mixture of anhydrous aluminium chloride (0.03 mol) and 2-methyl-phenyl-4-fluorobenzoate (0.02 mol) in dry nitrobenzene (40 ml) was protected from moisture by calcium chloride guard tube and refluxed at 80–900 °C with stirring for 45 min. At the end of this period the solution was cooled and decomposed by acidulated ice-cold water. Nitrobenzene was removed by steam distillation. The residual solid was crushed into powder, dissolved in ether and extracted with 10 percent sodium hydroxide. The basic aqueous solution was neutralized with 10 percent hydrochloric acid. The filtered solid was washed with distilled water and recrystallized from ethanol to afford pale yellow needles of (4-fluorophenyl)(4-hydroxy-3-methylphenyl)methanone.

Structure description top

For the biological activities of benzophenone derivatives, see: Khanum et al. (2004); Naveen et al. (2006); Selvi et al. (2003). For related structures, see: Mahendra et al. (2005); Dileep, Lakshmi Ranganatha et al. (2013); Dileep, Prashanth et al. (2013). For organic bond-length data, see: Allen et al. (12987).

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: Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. An ORTEP view of the title compound with the atom-labeling scheme. The thermal ellipsoids are drawn at the 50% probability level.
	Fig. 2. A molecular packing view of the title compound down the a axis, showing hydrogen bonds between the molecules.

(4-Hydroxy-3-methylphenyl)(4-fluorophenyl)methanone top

Crystal data top

C₁₄H₁₁FO₂	F(000) = 480
M_r = 230.23	D_x = 1.362 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yn	Cell parameters from 1769 reflections
a = 5.9265 (10) Å	θ = 4.6–64.5°
b = 13.112 (2) Å	µ = 0.85 mm⁻¹
c = 14.556 (2) Å	T = 296 K
β = 96.875 (7)°	Block, colorless
V = 1123.0 (3) Å³	0.27 × 0.25 × 0.23 mm
Z = 4

Data collection top

Bruker X8 Proteum diffractometer	1769 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode	1317 reflections with I > 2σ(I)
Helios multilayer optics monochromator	R_int = 0.065
Detector resolution: 10.7 pixels mm^-1	θ_max = 64.5°, θ_min = 4.6°
φ and ω scans	h = −3→6
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −15→15
T_min = 0.804, T_max = 0.829	l = −16→16
7047 measured reflections

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.273	H-atom parameters constrained
S = 1.16	w = 1/[σ²(F_o²) + (0.197P)²] where P = (F_o² + 2F_c²)/3
1769 reflections	(Δ/σ)_max = 0.007
155 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₄H₁₁FO₂	V = 1123.0 (3) Å³
M_r = 230.23	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 5.9265 (10) Å	µ = 0.85 mm⁻¹
b = 13.112 (2) Å	T = 296 K
c = 14.556 (2) Å	0.27 × 0.25 × 0.23 mm
β = 96.875 (7)°

Data collection top

Bruker X8 Proteum diffractometer	1769 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	1317 reflections with I > 2σ(I)
T_min = 0.804, T_max = 0.829	R_int = 0.065
7047 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	0 restraints
wR(F²) = 0.273	H-atom parameters constrained
S = 1.16	Δρ_max = 0.27 e Å⁻³
1769 reflections	Δρ_min = −0.36 e Å⁻³
155 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
F1	−0.8701 (4)	0.08743 (17)	0.39982 (15)	0.0892 (9)
O9	−0.0623 (4)	0.14888 (15)	0.71425 (13)	0.0602 (8)
O14	0.1969 (4)	0.61296 (12)	0.66191 (12)	0.0526 (8)
C2	−0.6901 (6)	0.1166 (2)	0.4605 (2)	0.0549 (10)
C3	−0.6834 (6)	0.0875 (2)	0.5518 (2)	0.0565 (10)
C4	−0.4989 (5)	0.11772 (18)	0.61269 (17)	0.0480 (10)
C5	−0.3285 (5)	0.17959 (17)	0.58441 (15)	0.0402 (8)
C6	−0.3409 (5)	0.20673 (18)	0.49111 (16)	0.0464 (9)
C7	−0.5214 (6)	0.1741 (2)	0.42877 (17)	0.0544 (9)
C8	−0.1343 (5)	0.21080 (19)	0.65391 (15)	0.0420 (8)
C10	−0.0411 (5)	0.31539 (18)	0.65178 (16)	0.0386 (8)
C11	0.1779 (5)	0.3367 (2)	0.69635 (17)	0.0443 (9)
C12	0.2609 (5)	0.43554 (19)	0.69977 (16)	0.0440 (9)
C13	0.1231 (5)	0.51463 (17)	0.65931 (14)	0.0385 (8)
C15	−0.0954 (5)	0.49616 (18)	0.61519 (15)	0.0395 (8)
C16	−0.2400 (5)	0.5833 (2)	0.57530 (19)	0.0502 (10)
C17	−0.1731 (5)	0.39631 (17)	0.61220 (15)	0.0397 (8)
H3	−0.79970	0.04880	0.57170	0.0680*
H4	−0.48790	0.09630	0.67400	0.0580*
H6	−0.22750	0.24690	0.47080	0.0560*
H7	−0.52850	0.19070	0.36640	0.0650*
H11	0.26740	0.28410	0.72370	0.0530*
H12	0.40630	0.44940	0.72860	0.0530*
H14	0.32560	0.61580	0.68970	0.0790*
H16A	−0.18110	0.60860	0.52110	0.0750*
H16B	−0.23820	0.63690	0.62030	0.0750*
H16C	−0.39320	0.56010	0.55900	0.0750*
H17	−0.31810	0.38260	0.58290	0.0480*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0791 (16)	0.0866 (15)	0.0952 (15)	−0.0148 (13)	−0.0165 (15)	−0.0221 (11)
O9	0.0725 (17)	0.0477 (12)	0.0571 (11)	−0.0012 (11)	−0.0052 (12)	0.0163 (8)
O14	0.0604 (15)	0.0388 (12)	0.0564 (12)	−0.0082 (9)	−0.0018 (11)	−0.0009 (7)
C2	0.0504 (19)	0.0456 (16)	0.0657 (16)	−0.0019 (15)	−0.0059 (16)	−0.0159 (13)
C3	0.053 (2)	0.0429 (15)	0.0758 (18)	−0.0103 (16)	0.0174 (17)	−0.0100 (13)
C4	0.056 (2)	0.0390 (15)	0.0514 (14)	−0.0040 (13)	0.0167 (15)	0.0008 (10)
C5	0.0481 (17)	0.0279 (12)	0.0455 (12)	0.0003 (12)	0.0088 (13)	−0.0005 (9)
C6	0.055 (2)	0.0371 (14)	0.0478 (13)	−0.0018 (13)	0.0087 (15)	0.0038 (9)
C7	0.072 (2)	0.0454 (15)	0.0437 (13)	0.0038 (16)	−0.0011 (16)	−0.0018 (10)
C8	0.0462 (17)	0.0369 (13)	0.0437 (12)	0.0020 (12)	0.0087 (13)	0.0028 (9)
C10	0.0408 (17)	0.0354 (13)	0.0393 (11)	0.0018 (11)	0.0038 (12)	0.0004 (9)
C11	0.0446 (18)	0.0412 (14)	0.0473 (13)	0.0052 (13)	0.0058 (13)	0.0038 (9)
C12	0.0443 (17)	0.0438 (15)	0.0435 (13)	0.0000 (13)	0.0034 (14)	0.0001 (10)
C13	0.0428 (16)	0.0360 (13)	0.0367 (11)	−0.0039 (12)	0.0052 (12)	−0.0038 (8)
C15	0.0451 (18)	0.0356 (13)	0.0380 (12)	0.0042 (12)	0.0064 (12)	−0.0029 (9)
C16	0.052 (2)	0.0404 (15)	0.0571 (15)	0.0081 (14)	0.0018 (16)	0.0004 (10)
C17	0.0392 (17)	0.0391 (13)	0.0408 (12)	0.0006 (12)	0.0052 (12)	−0.0041 (9)

Geometric parameters (Å, º) top

F1—C2	1.356 (4)	C12—C13	1.405 (4)
O9—C8	1.234 (3)	C13—C15	1.396 (4)
O14—C13	1.361 (3)	C15—C16	1.503 (4)
O14—H14	0.8200	C15—C17	1.387 (3)
C2—C7	1.376 (5)	C3—H3	0.9300
C2—C3	1.379 (4)	C4—H4	0.9300
C3—C4	1.381 (4)	C6—H6	0.9300
C4—C5	1.395 (4)	C7—H7	0.9300
C5—C6	1.397 (3)	C11—H11	0.9300
C5—C8	1.496 (4)	C12—H12	0.9300
C6—C7	1.385 (4)	C16—H16A	0.9600
C8—C10	1.480 (4)	C16—H16B	0.9600
C10—C17	1.401 (4)	C16—H16C	0.9600
C10—C11	1.408 (4)	C17—H17	0.9300
C11—C12	1.385 (4)

F1···H3ⁱ	2.7200	C17···H6	2.8300
F1···H12ⁱⁱ	2.7200	C17···H16A^vii	3.0200
O9···O14ⁱⁱⁱ	2.688 (3)	H3···F1ⁱ	2.7200
O14···O9^iv	2.688 (3)	H4···O9	2.6100
O9···H4	2.6100	H4···O14^v	2.8300
O9···H12ⁱⁱⁱ	2.8600	H4···C13^v	2.8500
O9···H14ⁱⁱⁱ	1.9100	H6···C10	2.8800
O9···H16B^v	2.8100	H6···C17	2.8300
O9···H11	2.6300	H6···H17	2.5200
O14···H16A	2.8500	H6···O14^vii	2.6900
O14···H16B	2.6000	H7···C11^xiii	2.9100
O14···H4^vi	2.8300	H11···O9	2.6300
O14···H11^iv	2.7900	H11···O14ⁱⁱⁱ	2.7900
O14···H6^vii	2.6900	H12···H14	2.2900
C2···C3^viii	3.491 (4)	H12···O9^iv	2.8600
C2···C4^viii	3.481 (4)	H12···F1^xiv	2.7200
C3···C8^ix	3.594 (4)	H14···H12	2.2900
C3···C2^viii	3.491 (4)	H14···O9^iv	1.9100
C4···C2^viii	3.481 (4)	H14···C8^iv	3.0100
C6···C17	3.139 (3)	H16A···O14	2.8500
C7···C16^x	3.479 (4)	H16A···C15^vii	3.0500
C8···C3^xi	3.594 (4)	H16A···C17^vii	3.0200
C16···C7^x	3.479 (4)	H16B···O14	2.6000
C17···C6	3.139 (3)	H16B···O9^vi	2.8100
C5···H17	2.6600	H16B···C7^x	2.9000
C6···H17	2.6600	H16C···H17	2.3900
C7···H16B^x	2.9000	H16C···H16C^x	2.5500
C8···H14ⁱⁱⁱ	3.0100	H17···C5	2.6600
C10···H6	2.8800	H17···C6	2.6600
C11···H7^xii	2.9100	H17···H6	2.5200
C13···H4^vi	2.8500	H17···H16C	2.3900
C15···H16A^vii	3.0500

C13—O14—H14	109.00	C16—C15—C17	122.3 (3)
F1—C2—C7	118.9 (3)	C13—C15—C17	117.7 (2)
C3—C2—C7	122.5 (3)	C10—C17—C15	122.4 (3)
F1—C2—C3	118.7 (3)	C2—C3—H3	121.00
C2—C3—C4	117.9 (3)	C4—C3—H3	121.00
C3—C4—C5	121.5 (2)	C3—C4—H4	119.00
C4—C5—C6	118.6 (2)	C5—C4—H4	119.00
C4—C5—C8	119.0 (2)	C5—C6—H6	120.00
C6—C5—C8	122.3 (2)	C7—C6—H6	120.00
C5—C6—C7	120.3 (3)	C2—C7—H7	120.00
C2—C7—C6	119.0 (2)	C6—C7—H7	121.00
O9—C8—C10	121.8 (2)	C10—C11—H11	120.00
C5—C8—C10	119.9 (2)	C12—C11—H11	120.00
O9—C8—C5	118.3 (2)	C11—C12—H12	120.00
C8—C10—C11	120.0 (2)	C13—C12—H12	120.00
C8—C10—C17	121.3 (3)	C15—C16—H16A	110.00
C11—C10—C17	118.6 (2)	C15—C16—H16B	109.00
C10—C11—C12	120.4 (2)	C15—C16—H16C	109.00
C11—C12—C13	119.3 (3)	H16A—C16—H16B	109.00
O14—C13—C15	117.0 (2)	H16A—C16—H16C	109.00
C12—C13—C15	121.7 (2)	H16B—C16—H16C	109.00
O14—C13—C12	121.3 (2)	C10—C17—H17	119.00
C13—C15—C16	120.0 (2)	C15—C17—H17	119.00

F1—C2—C3—C4	179.9 (2)	C5—C8—C10—C11	−160.8 (2)
C7—C2—C3—C4	−0.1 (4)	C5—C8—C10—C17	24.2 (4)
F1—C2—C7—C6	178.0 (3)	C8—C10—C11—C12	−175.9 (2)
C3—C2—C7—C6	−2.0 (4)	C17—C10—C11—C12	−0.7 (4)
C2—C3—C4—C5	2.8 (4)	C8—C10—C17—C15	175.3 (2)
C3—C4—C5—C6	−3.3 (4)	C11—C10—C17—C15	0.2 (4)
C3—C4—C5—C8	179.3 (2)	C10—C11—C12—C13	0.8 (4)
C4—C5—C6—C7	1.2 (4)	C11—C12—C13—O14	179.3 (2)
C8—C5—C6—C7	178.5 (2)	C11—C12—C13—C15	−0.4 (4)
C4—C5—C8—O9	36.2 (4)	O14—C13—C15—C16	−1.5 (3)
C4—C5—C8—C10	−140.9 (3)	O14—C13—C15—C17	−179.9 (2)
C6—C5—C8—O9	−141.1 (3)	C12—C13—C15—C16	178.2 (2)
C6—C5—C8—C10	41.8 (4)	C12—C13—C15—C17	−0.2 (3)
C5—C6—C7—C2	1.4 (4)	C13—C15—C17—C10	0.3 (4)
O9—C8—C10—C11	22.2 (4)	C16—C15—C17—C10	−178.0 (2)
O9—C8—C10—C17	−152.8 (3)

Symmetry codes: (i) −x−2, −y, −z+1; (ii) x−3/2, −y+1/2, z−1/2; (iii) −x+1/2, y−1/2, −z+3/2; (iv) −x+1/2, y+1/2, −z+3/2; (v) −x−1/2, y−1/2, −z+3/2; (vi) −x−1/2, y+1/2, −z+3/2; (vii) −x, −y+1, −z+1; (viii) −x−1, −y, −z+1; (ix) x−1, y, z; (x) −x−1, −y+1, −z+1; (xi) x+1, y, z; (xii) x+1/2, −y+1/2, z+1/2; (xiii) x−1/2, −y+1/2, z−1/2; (xiv) x+3/2, −y+1/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O14—H14···O9^iv	0.82	1.91	2.688 (3)	158

Symmetry code: (iv) −x+1/2, y+1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O14—H14···O9ⁱ	0.82	1.91	2.688 (3)	158

Symmetry code: (i) −x+1/2, y+1/2, −z+3/2.

Acknowledgements

The authors would like to thank the University of Mysore for providing the diffractometer facility under IoE. CSD would like to thank the University of Mysore for awarding an RFSMS fellowship under the head DV5/Physics/389/RFSMS/2009–2010/10.07.2012. 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 UGC under major research project scheme [F.39/737/2010 (SR)].

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