organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

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.

Related literature

For the biological activities of benzo­phenone derivatives, see: Khanum et al. (2004[Khanum, S. A., Venu, T. D., Shashikanth, S. & Firdouse, A. (2004). Bioorg. Med. Chem. Lett. 12, 2093-2095.]); Naveen et al. (2006[Naveen, S., Khanum, S. A., Devaiah, V. T., Shashikanth, S., Anandalwar, S. M. & Prasad, S. (2006). Anal. Sci. 22, 183-184.]); Selvi et al. (2003[Selvi, A. T., Joseph, G. S. & Jayaprakasha, G. K. (2003). Food Microbiol. 20, 455-460.]). For related structures, see: Mahendra et al. (2005[Mahendra, M., Khanum, S. A., Singh, A. K., Shashikanth, S., Doreswamy, B. H., Sridhar, M. A. & Shashidhara Prasad, J. (2005). Acta Cryst. E61, o2990-o2991.]); Dileep, Lakshmi Ranganatha et al. (2013[Dileep, C. S., Lakshmi Ranganatha, V., Lokanath, N. K., Shaukath, A. K. & Sridhar, M. A. (2013). Acta Cryst. E69, o1550.]); Dileep, Prashanth et al. (2013[Dileep, C. S., Prashanth, T., Jeyaseelan, S., Khanum, S. A. & Sridhar, M. A. (2013). Acta Cryst. E69, o1676.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C14H11FO2

  • Mr = 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[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.804, Tmax = 0.829

  • 7047 measured reflections

  • 1769 independent reflections

  • 1317 reflections with I > 2σ(I)

  • Rint = 0.065

Refinement
  • R[F2 > 2σ(F2)] = 0.068

  • wR(F2) = 0.273

  • S = 1.16

  • 1769 reflections

  • 155 parameters

  • H-atom parameters constrained

  • Δρmax = 0.27 e Å−3

  • Δρmin = −0.36 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: SHELXL97.

Supporting information


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.

Refinement top

All H-atoms were located from difference maps and were positioned geometrically and refined using a riding model with C—H = 0.93–0.96 Å and O—H = 0.82 Å, and with Uiso(H) = 1.2Ueq(Caromatic) or 1.5Ueq(O, Cmethyl). The data collection did not yield reflections with measurable intensity range as the crystal was diffracting a bit poorly. Hence, the range is slightly less (64.45° rather than the required 65°).

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
[Figure 1] Fig. 1. An ORTEP view of the title compound with the atom-labeling scheme. The thermal ellipsoids are drawn at the 50% probability level.
[Figure 2] 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
C14H11FO2F(000) = 480
Mr = 230.23Dx = 1.362 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ynCell parameters from 1769 reflections
a = 5.9265 (10) Åθ = 4.6–64.5°
b = 13.112 (2) ŵ = 0.85 mm1
c = 14.556 (2) ÅT = 296 K
β = 96.875 (7)°Block, colorless
V = 1123.0 (3) Å30.27 × 0.25 × 0.23 mm
Z = 4
Data collection top
Bruker X8 Proteum
diffractometer
1769 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode1317 reflections with I > 2σ(I)
Helios multilayer optics monochromatorRint = 0.065
Detector resolution: 10.7 pixels mm-1θmax = 64.5°, θmin = 4.6°
ϕ and ω scansh = 36
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1515
Tmin = 0.804, Tmax = 0.829l = 1616
7047 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.273H-atom parameters constrained
S = 1.16 w = 1/[σ2(Fo2) + (0.197P)2]
where P = (Fo2 + 2Fc2)/3
1769 reflections(Δ/σ)max = 0.007
155 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.36 e Å3
Crystal data top
C14H11FO2V = 1123.0 (3) Å3
Mr = 230.23Z = 4
Monoclinic, P21/nCu Kα radiation
a = 5.9265 (10) ŵ = 0.85 mm1
b = 13.112 (2) ÅT = 296 K
c = 14.556 (2) Å0.27 × 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)
Tmin = 0.804, Tmax = 0.829Rint = 0.065
7047 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0680 restraints
wR(F2) = 0.273H-atom parameters constrained
S = 1.16Δρmax = 0.27 e Å3
1769 reflectionsΔρmin = 0.36 e Å3
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
xyzUiso*/Ueq
F10.8701 (4)0.08743 (17)0.39982 (15)0.0892 (9)
O90.0623 (4)0.14888 (15)0.71425 (13)0.0602 (8)
O140.1969 (4)0.61296 (12)0.66191 (12)0.0526 (8)
C20.6901 (6)0.1166 (2)0.4605 (2)0.0549 (10)
C30.6834 (6)0.0875 (2)0.5518 (2)0.0565 (10)
C40.4989 (5)0.11772 (18)0.61269 (17)0.0480 (10)
C50.3285 (5)0.17959 (17)0.58441 (15)0.0402 (8)
C60.3409 (5)0.20673 (18)0.49111 (16)0.0464 (9)
C70.5214 (6)0.1741 (2)0.42877 (17)0.0544 (9)
C80.1343 (5)0.21080 (19)0.65391 (15)0.0420 (8)
C100.0411 (5)0.31539 (18)0.65178 (16)0.0386 (8)
C110.1779 (5)0.3367 (2)0.69635 (17)0.0443 (9)
C120.2609 (5)0.43554 (19)0.69977 (16)0.0440 (9)
C130.1231 (5)0.51463 (17)0.65931 (14)0.0385 (8)
C150.0954 (5)0.49616 (18)0.61519 (15)0.0395 (8)
C160.2400 (5)0.5833 (2)0.57530 (19)0.0502 (10)
C170.1731 (5)0.39631 (17)0.61220 (15)0.0397 (8)
H30.799700.048800.571700.0680*
H40.487900.096300.674000.0580*
H60.227500.246900.470800.0560*
H70.528500.190700.366400.0650*
H110.267400.284100.723700.0530*
H120.406300.449400.728600.0530*
H140.325600.615800.689700.0790*
H16A0.181100.608600.521100.0750*
H16B0.238200.636900.620300.0750*
H16C0.393200.560100.559000.0750*
H170.318100.382600.582900.0480*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0791 (16)0.0866 (15)0.0952 (15)0.0148 (13)0.0165 (15)0.0221 (11)
O90.0725 (17)0.0477 (12)0.0571 (11)0.0012 (11)0.0052 (12)0.0163 (8)
O140.0604 (15)0.0388 (12)0.0564 (12)0.0082 (9)0.0018 (11)0.0009 (7)
C20.0504 (19)0.0456 (16)0.0657 (16)0.0019 (15)0.0059 (16)0.0159 (13)
C30.053 (2)0.0429 (15)0.0758 (18)0.0103 (16)0.0174 (17)0.0100 (13)
C40.056 (2)0.0390 (15)0.0514 (14)0.0040 (13)0.0167 (15)0.0008 (10)
C50.0481 (17)0.0279 (12)0.0455 (12)0.0003 (12)0.0088 (13)0.0005 (9)
C60.055 (2)0.0371 (14)0.0478 (13)0.0018 (13)0.0087 (15)0.0038 (9)
C70.072 (2)0.0454 (15)0.0437 (13)0.0038 (16)0.0011 (16)0.0018 (10)
C80.0462 (17)0.0369 (13)0.0437 (12)0.0020 (12)0.0087 (13)0.0028 (9)
C100.0408 (17)0.0354 (13)0.0393 (11)0.0018 (11)0.0038 (12)0.0004 (9)
C110.0446 (18)0.0412 (14)0.0473 (13)0.0052 (13)0.0058 (13)0.0038 (9)
C120.0443 (17)0.0438 (15)0.0435 (13)0.0000 (13)0.0034 (14)0.0001 (10)
C130.0428 (16)0.0360 (13)0.0367 (11)0.0039 (12)0.0052 (12)0.0038 (8)
C150.0451 (18)0.0356 (13)0.0380 (12)0.0042 (12)0.0064 (12)0.0029 (9)
C160.052 (2)0.0404 (15)0.0571 (15)0.0081 (14)0.0018 (16)0.0004 (10)
C170.0392 (17)0.0391 (13)0.0408 (12)0.0006 (12)0.0052 (12)0.0041 (9)
Geometric parameters (Å, º) top
F1—C21.356 (4)C12—C131.405 (4)
O9—C81.234 (3)C13—C151.396 (4)
O14—C131.361 (3)C15—C161.503 (4)
O14—H140.8200C15—C171.387 (3)
C2—C71.376 (5)C3—H30.9300
C2—C31.379 (4)C4—H40.9300
C3—C41.381 (4)C6—H60.9300
C4—C51.395 (4)C7—H70.9300
C5—C61.397 (3)C11—H110.9300
C5—C81.496 (4)C12—H120.9300
C6—C71.385 (4)C16—H16A0.9600
C8—C101.480 (4)C16—H16B0.9600
C10—C171.401 (4)C16—H16C0.9600
C10—C111.408 (4)C17—H170.9300
C11—C121.385 (4)
F1···H3i2.7200C17···H62.8300
F1···H12ii2.7200C17···H16Avii3.0200
O9···O14iii2.688 (3)H3···F1i2.7200
O14···O9iv2.688 (3)H4···O92.6100
O9···H42.6100H4···O14v2.8300
O9···H12iii2.8600H4···C13v2.8500
O9···H14iii1.9100H6···C102.8800
O9···H16Bv2.8100H6···C172.8300
O9···H112.6300H6···H172.5200
O14···H16A2.8500H6···O14vii2.6900
O14···H16B2.6000H7···C11xiii2.9100
O14···H4vi2.8300H11···O92.6300
O14···H11iv2.7900H11···O14iii2.7900
O14···H6vii2.6900H12···H142.2900
C2···C3viii3.491 (4)H12···O9iv2.8600
C2···C4viii3.481 (4)H12···F1xiv2.7200
C3···C8ix3.594 (4)H14···H122.2900
C3···C2viii3.491 (4)H14···O9iv1.9100
C4···C2viii3.481 (4)H14···C8iv3.0100
C6···C173.139 (3)H16A···O142.8500
C7···C16x3.479 (4)H16A···C15vii3.0500
C8···C3xi3.594 (4)H16A···C17vii3.0200
C16···C7x3.479 (4)H16B···O142.6000
C17···C63.139 (3)H16B···O9vi2.8100
C5···H172.6600H16B···C7x2.9000
C6···H172.6600H16C···H172.3900
C7···H16Bx2.9000H16C···H16Cx2.5500
C8···H14iii3.0100H17···C52.6600
C10···H62.8800H17···C62.6600
C11···H7xii2.9100H17···H62.5200
C13···H4vi2.8500H17···H16C2.3900
C15···H16Avii3.0500
C13—O14—H14109.00C16—C15—C17122.3 (3)
F1—C2—C7118.9 (3)C13—C15—C17117.7 (2)
C3—C2—C7122.5 (3)C10—C17—C15122.4 (3)
F1—C2—C3118.7 (3)C2—C3—H3121.00
C2—C3—C4117.9 (3)C4—C3—H3121.00
C3—C4—C5121.5 (2)C3—C4—H4119.00
C4—C5—C6118.6 (2)C5—C4—H4119.00
C4—C5—C8119.0 (2)C5—C6—H6120.00
C6—C5—C8122.3 (2)C7—C6—H6120.00
C5—C6—C7120.3 (3)C2—C7—H7120.00
C2—C7—C6119.0 (2)C6—C7—H7121.00
O9—C8—C10121.8 (2)C10—C11—H11120.00
C5—C8—C10119.9 (2)C12—C11—H11120.00
O9—C8—C5118.3 (2)C11—C12—H12120.00
C8—C10—C11120.0 (2)C13—C12—H12120.00
C8—C10—C17121.3 (3)C15—C16—H16A110.00
C11—C10—C17118.6 (2)C15—C16—H16B109.00
C10—C11—C12120.4 (2)C15—C16—H16C109.00
C11—C12—C13119.3 (3)H16A—C16—H16B109.00
O14—C13—C15117.0 (2)H16A—C16—H16C109.00
C12—C13—C15121.7 (2)H16B—C16—H16C109.00
O14—C13—C12121.3 (2)C10—C17—H17119.00
C13—C15—C16120.0 (2)C15—C17—H17119.00
F1—C2—C3—C4179.9 (2)C5—C8—C10—C11160.8 (2)
C7—C2—C3—C40.1 (4)C5—C8—C10—C1724.2 (4)
F1—C2—C7—C6178.0 (3)C8—C10—C11—C12175.9 (2)
C3—C2—C7—C62.0 (4)C17—C10—C11—C120.7 (4)
C2—C3—C4—C52.8 (4)C8—C10—C17—C15175.3 (2)
C3—C4—C5—C63.3 (4)C11—C10—C17—C150.2 (4)
C3—C4—C5—C8179.3 (2)C10—C11—C12—C130.8 (4)
C4—C5—C6—C71.2 (4)C11—C12—C13—O14179.3 (2)
C8—C5—C6—C7178.5 (2)C11—C12—C13—C150.4 (4)
C4—C5—C8—O936.2 (4)O14—C13—C15—C161.5 (3)
C4—C5—C8—C10140.9 (3)O14—C13—C15—C17179.9 (2)
C6—C5—C8—O9141.1 (3)C12—C13—C15—C16178.2 (2)
C6—C5—C8—C1041.8 (4)C12—C13—C15—C170.2 (3)
C5—C6—C7—C21.4 (4)C13—C15—C17—C100.3 (4)
O9—C8—C10—C1122.2 (4)C16—C15—C17—C10178.0 (2)
O9—C8—C10—C17152.8 (3)
Symmetry codes: (i) x2, y, z+1; (ii) x3/2, y+1/2, z1/2; (iii) x+1/2, y1/2, z+3/2; (iv) x+1/2, y+1/2, z+3/2; (v) x1/2, y1/2, z+3/2; (vi) x1/2, y+1/2, z+3/2; (vii) x, y+1, z+1; (viii) x1, y, z+1; (ix) x1, y, z; (x) x1, y+1, z+1; (xi) x+1, y, z; (xii) x+1/2, y+1/2, z+1/2; (xiii) x1/2, y+1/2, z1/2; (xiv) x+3/2, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O14—H14···O9iv0.821.912.688 (3)158
Symmetry code: (iv) x+1/2, y+1/2, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O14—H14···O9i0.821.912.688 (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)].

References

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