(4-Fluoro­phen­yl)(2-hy­droxy-5-methyl­phen­yl)methanone

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

doi:10.1107/S1600536814001883

organic compounds

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Volume 70| Part 3| March 2014| Page o286

doi:10.1107/S1600536814001883

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(4-Fluorophenyl)(2-hydroxy-5-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 26 January 2014; accepted 27 January 2014; online 12 February 2014)

In the title compound, C₁₄H₁₁FO₂, the dihedral angles beteen the central C₃O ketone residue and the fluoro- and hydroxy-substituted benzene rings are 50.44 (9) and 12.63 (10)°, respectively. The planes of the benzene rings subtend a dihedral angle of 58.88 (9)° and an intramolecular O—H⋯O hydrogen bond closes an S(6) ring. No directional interactions beyond van der Waals packing contacts were identified in the crystal structure.

CCDC reference: 983671

Related literature

For related structures, see: Dileep et al. (2013 ); Mahendra et al. (2005 ).

Experimental

Crystal data

C₁₄H₁₁FO₂
M_r = 230.23
Orthorhombic, P b c a
a = 5.9396 (6) Å
b = 12.3808 (15) Å
c = 30.522 (3) Å
V = 2244.5 (4) Å³
Z = 8
Cu Kα radiation
μ = 0.85 mm⁻¹
T = 296 K
0.28 × 0.25 × 0.22 mm

Data collection

Bruker X8 Proteum CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2013 ) T_min = 0.798, T_max = 0.836
8509 measured reflections
1822 independent reflections
1535 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.135
S = 1.06
1822 reflections
156 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.82	1.86	2.574 (2)	146

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); 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., 2008 ); software used to prepare material for publication: Mercury.

Supporting information

CCDC reference: 983671

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814001883/hb7191sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814001883/hb7191Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814001883/hb7191Isup3.cml

checkCIF report

Comment top

As part of our structural studies of benzophenone derivatives (Dileep et al., 2013), the title compound was prepared and characterized by single-crystal X-ray diffraction.

The mean plane angle between the phenyl rings (/C1C2/C3/C4/C5/C6) and (C9/C10/C11/C12/C13/C14) is 58.88°.

The position of C8 atom is distorted trigonal planar geometry as indicated by bond angle values (O2—C8—C6)=121.05°, (O2—C8—C9) =118.37°, (N6—C8—C9)= 120.56°.

The conformation of the attachment of the two phenyl rings to the central carbonyl group can also be characterized by torsion angles (O2—C8—C6—C5) and (O2—C8—C9—C10) of -165.31° and -129.32°, respectively.

The crystal structure exhibits intramolecular O(1)—H(1)···O(2) hydrogen bonds. The bond angle between (O1—C1—C2) and(O1—C1—C6) is 118.61° and 122.22°. The bond length between (O1—C2) and (O2—C8) is 1.351 Å and 1.238 Å. The molecular packing when viewed down the a axis is shown in Fig. 2.

Related literature top

For related structures, see: Dileep et al. (2013); Mahendra et al. (2005).

Experimental top

A mixture of anhydrous aluminium chloride (0.03 mol) and 4-fluoro-benzoic acid p-tolyl ester (0.02 mol) in dry nitrobenzene (40 ml) was protected from moisture by calcium chloride guard tube and refluxed 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% sodium hydroxide. The basic aqueous solution was neutralized with 10% hydrochloric acid. The filtered solid was washed with distilled water and recrystallized from ethanol solution to afford pale yellow blocks of the title compound.

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: Mercury (Macrae et al., 2008).

Figures top

	Fig. 1. ORTEP view of the molecule with dispalcement ellipsoids drawn at the 50% probability level.
	Fig. 2. A molecular packing view of the title compound down the a-axis.

(4-Fluorophenyl)(2-hydroxy-5-methylphenyl)methanone top

Crystal data top

C₁₄H₁₁FO₂	F(000) = 960
M_r = 230.23	D_x = 1.363 Mg m⁻³
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 8509 reflections
a = 5.9396 (6) Å	θ = 5.8–64.4°
b = 12.3808 (15) Å	µ = 0.85 mm⁻¹
c = 30.522 (3) Å	T = 296 K
V = 2244.5 (4) Å³	Block, pale yellow
Z = 8	0.28 × 0.25 × 0.22 mm

Data collection top

Bruker X8 Proteum CCD diffractometer	1822 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode	1535 reflections with I > 2σ(I)
Helios multilayer optics monochromator	R_int = 0.030
Detector resolution: 10.7 pixels mm^-1	θ_max = 64.4°, θ_min = 5.8°
φ and ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −14→8
T_min = 0.798, T_max = 0.836	l = −34→35
8509 measured 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)] = 0.047	H-atom parameters constrained
wR(F²) = 0.135	w = 1/[σ²(F_o²) + (0.0857P)² + 0.3925P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
1822 reflections	Δρ_max = 0.18 e Å⁻³
156 parameters	Δρ_min = −0.21 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: 0.0018 (4)

Crystal data top

C₁₄H₁₁FO₂	V = 2244.5 (4) Å³
M_r = 230.23	Z = 8
Orthorhombic, Pbca	Cu Kα radiation
a = 5.9396 (6) Å	µ = 0.85 mm⁻¹
b = 12.3808 (15) Å	T = 296 K
c = 30.522 (3) Å	0.28 × 0.25 × 0.22 mm

Data collection top

Bruker X8 Proteum CCD diffractometer	1822 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2013)	1535 reflections with I > 2σ(I)
T_min = 0.798, T_max = 0.836	R_int = 0.030
8509 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.06	Δρ_max = 0.18 e Å⁻³
1822 reflections	Δρ_min = −0.21 e Å⁻³
156 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	0.2531 (2)	0.47588 (9)	0.01429 (4)	0.0737 (5)
O1	−0.0006 (3)	−0.11052 (11)	0.14523 (5)	0.0738 (6)
O2	−0.1159 (2)	0.05347 (12)	0.09849 (5)	0.0682 (5)
C1	0.1798 (4)	−0.05074 (14)	0.15707 (6)	0.0552 (6)
C2	0.3280 (4)	−0.09271 (16)	0.18766 (7)	0.0692 (8)
C3	0.5047 (4)	−0.0321 (2)	0.20256 (6)	0.0699 (8)
C4	0.5444 (3)	0.07352 (18)	0.18787 (6)	0.0576 (6)
C5	0.4015 (3)	0.11264 (14)	0.15595 (5)	0.0471 (6)
C6	0.2213 (3)	0.05270 (13)	0.13940 (5)	0.0453 (5)
C7	0.7297 (4)	0.1418 (2)	0.20654 (7)	0.0776 (9)
C8	0.0668 (3)	0.09745 (15)	0.10646 (6)	0.0469 (6)
C9	0.1246 (3)	0.19838 (13)	0.08253 (5)	0.0414 (5)
C10	0.3293 (3)	0.21172 (14)	0.06101 (5)	0.0455 (5)
C11	0.3715 (3)	0.30463 (15)	0.03721 (6)	0.0481 (6)
C12	0.2094 (3)	0.38360 (14)	0.03669 (5)	0.0482 (6)
C13	0.0073 (3)	0.37430 (16)	0.05775 (6)	0.0537 (6)
C14	−0.0356 (3)	0.27965 (15)	0.08026 (6)	0.0492 (6)
H1	−0.07480	−0.07740	0.12700	0.1110*
H2	0.30740	−0.16250	0.19810	0.0830*
H3	0.60200	−0.06200	0.22310	0.0840*
H5	0.42620	0.18170	0.14500	0.0560*
H7A	0.73900	0.20840	0.19050	0.1160*
H7B	0.87010	0.10380	0.20420	0.1160*
H7C	0.69850	0.15690	0.23680	0.1160*
H10	0.43820	0.15790	0.06260	0.0550*
H11	0.50590	0.31330	0.02200	0.0580*
H13	−0.09800	0.42990	0.05700	0.0640*
H14	−0.17390	0.27030	0.09410	0.0590*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0800 (9)	0.0591 (7)	0.0819 (8)	−0.0030 (6)	−0.0052 (6)	0.0248 (6)
O1	0.0938 (12)	0.0487 (8)	0.0789 (10)	−0.0156 (8)	0.0071 (8)	0.0023 (7)
O2	0.0575 (9)	0.0700 (9)	0.0770 (10)	−0.0208 (7)	−0.0081 (7)	0.0058 (7)
C1	0.0713 (13)	0.0429 (9)	0.0513 (10)	0.0047 (9)	0.0138 (9)	−0.0033 (8)
C2	0.1017 (18)	0.0495 (11)	0.0564 (11)	0.0150 (12)	0.0105 (12)	0.0081 (9)
C3	0.0838 (16)	0.0755 (15)	0.0504 (11)	0.0266 (13)	−0.0023 (10)	0.0123 (10)
C4	0.0560 (11)	0.0728 (12)	0.0440 (9)	0.0156 (10)	0.0005 (8)	−0.0009 (9)
C5	0.0489 (10)	0.0486 (10)	0.0437 (9)	0.0066 (8)	0.0050 (7)	0.0007 (7)
C6	0.0500 (10)	0.0418 (9)	0.0441 (9)	0.0054 (8)	0.0074 (7)	−0.0017 (7)
C7	0.0625 (13)	0.1073 (19)	0.0630 (13)	0.0040 (13)	−0.0148 (10)	−0.0016 (12)
C8	0.0427 (10)	0.0482 (10)	0.0499 (10)	−0.0023 (8)	0.0017 (7)	−0.0052 (7)
C9	0.0385 (9)	0.0446 (9)	0.0410 (8)	0.0014 (7)	−0.0049 (6)	−0.0032 (6)
C10	0.0397 (9)	0.0460 (9)	0.0507 (9)	0.0049 (7)	−0.0016 (7)	−0.0032 (7)
C11	0.0431 (10)	0.0555 (10)	0.0458 (9)	−0.0032 (8)	0.0002 (7)	−0.0001 (7)
C12	0.0533 (11)	0.0448 (9)	0.0464 (9)	−0.0029 (8)	−0.0095 (8)	0.0055 (7)
C13	0.0511 (11)	0.0516 (10)	0.0584 (11)	0.0127 (9)	−0.0062 (8)	0.0022 (8)
C14	0.0375 (9)	0.0591 (11)	0.0510 (10)	0.0048 (8)	−0.0015 (7)	−0.0009 (8)

Geometric parameters (Å, º) top

F1—C12	1.357 (2)	C10—C11	1.383 (3)
O1—C1	1.352 (3)	C11—C12	1.372 (3)
O2—C8	1.238 (2)	C12—C13	1.367 (2)
O1—H1	0.8200	C13—C14	1.382 (3)
C1—C6	1.411 (2)	C2—H2	0.9300
C1—C2	1.384 (3)	C3—H3	0.9300
C2—C3	1.368 (3)	C5—H5	0.9300
C3—C4	1.402 (3)	C7—H7A	0.9600
C4—C5	1.380 (2)	C7—H7B	0.9600
C4—C7	1.500 (3)	C7—H7C	0.9600
C5—C6	1.397 (2)	C10—H10	0.9300
C6—C8	1.470 (2)	C11—H11	0.9300
C8—C9	1.488 (2)	C13—H13	0.9300
C9—C14	1.387 (2)	C14—H14	0.9300
C9—C10	1.392 (2)

C1—O1—H1	110.00	C11—C12—C13	123.43 (17)
O1—C1—C6	122.23 (18)	C12—C13—C14	117.85 (17)
C2—C1—C6	119.16 (19)	C9—C14—C13	120.90 (16)
O1—C1—C2	118.61 (17)	C1—C2—H2	120.00
C1—C2—C3	120.41 (19)	C3—C2—H2	120.00
C2—C3—C4	122.29 (19)	C2—C3—H3	119.00
C3—C4—C5	116.72 (18)	C4—C3—H3	119.00
C3—C4—C7	121.83 (18)	C4—C5—H5	119.00
C5—C4—C7	121.44 (19)	C6—C5—H5	119.00
C4—C5—C6	122.69 (17)	C4—C7—H7A	109.00
C1—C6—C5	118.54 (16)	C4—C7—H7B	109.00
C5—C6—C8	121.70 (15)	C4—C7—H7C	109.00
C1—C6—C8	119.63 (16)	H7A—C7—H7B	109.00
O2—C8—C9	118.37 (16)	H7A—C7—H7C	110.00
C6—C8—C9	120.56 (15)	H7B—C7—H7C	110.00
O2—C8—C6	121.05 (17)	C9—C10—H10	120.00
C8—C9—C14	118.41 (16)	C11—C10—H10	120.00
C10—C9—C14	119.33 (15)	C10—C11—H11	121.00
C8—C9—C10	122.21 (15)	C12—C11—H11	121.00
C9—C10—C11	120.32 (16)	C12—C13—H13	121.00
C10—C11—C12	118.12 (16)	C14—C13—H13	121.00
F1—C12—C11	118.14 (15)	C9—C14—H14	120.00
F1—C12—C13	118.43 (16)	C13—C14—H14	120.00

O1—C1—C2—C3	−175.88 (19)	C5—C6—C8—C9	13.4 (3)
C6—C1—C2—C3	4.0 (3)	O2—C8—C9—C10	−129.33 (19)
O1—C1—C6—C5	174.98 (17)	O2—C8—C9—C14	48.0 (2)
O1—C1—C6—C8	−1.0 (3)	C6—C8—C9—C10	52.0 (2)
C2—C1—C6—C5	−4.9 (3)	C6—C8—C9—C14	−130.74 (18)
C2—C1—C6—C8	179.17 (18)	C8—C9—C10—C11	176.58 (16)
C1—C2—C3—C4	−0.1 (3)	C14—C9—C10—C11	−0.7 (2)
C2—C3—C4—C5	−2.7 (3)	C8—C9—C14—C13	−178.76 (17)
C2—C3—C4—C7	176.0 (2)	C10—C9—C14—C13	−1.4 (3)
C3—C4—C5—C6	1.7 (3)	C9—C10—C11—C12	2.0 (3)
C7—C4—C5—C6	−177.01 (17)	C10—C11—C12—F1	178.33 (15)
C4—C5—C6—C1	2.0 (3)	C10—C11—C12—C13	−1.3 (3)
C4—C5—C6—C8	177.92 (17)	F1—C12—C13—C14	179.67 (16)
C1—C6—C8—O2	10.5 (3)	C11—C12—C13—C14	−0.7 (3)
C1—C6—C8—C9	−170.79 (16)	C12—C13—C14—C9	2.1 (3)
C5—C6—C8—O2	−165.31 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.86	2.574 (2)	146

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.86	2.574 (2)	146

Acknowledgements

The authors thank the University of Mysore for providing the diffractometer facility under IoE. 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. 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 the Major Research Project scheme [F.39/737/2010 (SR)].

References

Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 3| March 2014| Page o286

doi:10.1107/S1600536814001883

Open

access