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

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.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.047
• wR factor = 0.135
• Data-to-parameter ratio = 11.7

checkCIF/PLATON results

No syntax errors found



Alert level C
THETM01_ALERT_3_C  The value of sine(theta_max)/wavelength is less than 0.590
            Calculated sin(theta_max)/wavelength =    0.5851
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......      0.971
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.551 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.585         54

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Why ?
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still          43 %
PLAT910_ALERT_3_G Missing # of FCF Reflections Below Th(Min) .....          1 Why ?

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

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S1. Comment

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

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

S2. Experimental

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.

S3. Refinement

All H-atoms were positioned geometrically and refined using a riding model with C–H= 0.93–0.9600 Å and U_iso(H)=1.2Ueq(C).

Computing details

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

	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

Crystal data

C14H11FO2	F(000) = 960
Mr = 230.23	Dx = 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) Å^3	Block, pale yellow
Z = 8	0.28 × 0.25 × 0.22 mm

Data collection

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	Rint = 0.030
Detector resolution: 10.7 pixels mm^-1	θmax = 64.4°, θmin = 5.8°
φ and ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −14→8
Tmin = 0.798, Tmax = 0.836	l = −34→35
8509 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H-atom parameters constrained
wR(F^2) = 0.135	w = 1/[σ^2(Fo^2) + (0.0857P)^2 + 0.3925P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
1822 reflections	Δρmax = 0.18 e Å^−3
156 parameters	Δρmin = −0.21 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), FC^*=KFC[1+0.001XFC^2Λ^3/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0018 (4)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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