1-(2-Hydr­oxy-5-methyl­phen­yl)-2-phenyl­ethanone

In the title compound, C₁₅H₁₄O₂, the dihedral angle between the two aromatic rings is 87.98 (13)°. The primary inter­action is an intra­molecular O—H...O=C inter­action [O...O = 2.559 (3) Å]. Inter­molecular inter­actions/contacts are weak and are of the O—H...C, C—H...π(arene) and π–π(arene) types [Cg...Cg() = 3.927 (1) Å; Cg is the centroid of the phenyl ring].

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.064
• wR factor = 0.242
• Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT031_ALERT_4_C Refined Extinction Parameter within Range ......       2.50 Sigma
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.47
PLAT334_ALERT_2_C Small Average Benzene C-C Dist.  C1     -C6            1.34 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

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

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S1. Comment

Benzophenones and related compounds have a wide variety of applications, in particular as biologically active compounds, which exhibit anti-inflammatory (Khanum et al., 2004), antifungal, antibacterial and anticancer activities·As an extension of work on the structural characterization of Benzophenone derivatives,the title compound, (I), was synthesized and its crystal structure is reported here.

The molecule of (I) is non-planar (Fig. 1). The dihedral angle between the two aromatic rings is 87.98 (13)°. The crystal structure is stabilized by intramolecular O—H···O hydrogen bonds and intermolecular O—H···C contacts together with C—H···π(arene) contacts and π···π stacking interactions, (Table 1, Fig. 2).

Related literature

For related literature, see: Khanum et al. (2004).

S2. Experimental

Phenylacetyl chloride (7.73 g, 0.05 mol) was added dropwise to p-cresol (5.41 g, 0.05 mol) and the mixture was reacted at room temperature for 1 h, then heated to 373 K for 2 h. After cooled to the ambient temperature, the CHCl₃ diluted mixture was washed with sodium carbonate solution and water for several times. The organic layer was dried with anhydrous sodium sulfate, filtered, and the solvent was removed. Further purification was carried out by vacuum distillation, 4-methylphenyl phenylacetate was obtained (yield 81.2%). Then the mixture of 4-methylphenyl phenylacetate (9.19 g, 0.041 mol) and anhydrous aluminium chloride (17.20 g, 0.129 mol) gradually heated to 373 K in 0.5 h, then heated to 423 K and kept for 30 min. The reaction mixture was cooled to room temperature, hydrolyzed, and extracted with 60 ml CHCl₃. The organic layer washed with water, dried with anhydrous sodium sulfate. Filtered, CHCl₃ was removed under reduced pressure. The residue was distilled under vacuum to obtain the title compound (I) (yield 76.1%)·The compound was recrystallized from ethyl acetate to obtain colourless single crystals suitable for X-ray diffraction.

S3. Refinement

All H atoms,were positioned geometrically and treated as riding on their parent atoms,with C—H(methyl) = 0.96 Å, C—H(methylene) = 0.97 Å, C—H(aromatic) = 0.93 Å, O—H = 0.82 Å, and with U_iso(H)=1.5U_eq(C_methyl,O) and 1.2U_eq(C_aromatic,C_methylene).

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. The molecular structure of compound (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Packing diagram of (I), showing intramolecular O—H···O and intermolecular O—H···C hydrogen bonds.(dashed lines).

1-(2-Hydroxy-5-methylphenyl)-2-phenylethanone

Crystal data

C15H14O2	F(000) = 480
Mr = 226.26	Dx = 1.236 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3447 reflections
a = 8.2951 (10) Å	θ = 2.3–25.1°
b = 18.010 (2) Å	µ = 0.08 mm^−1
c = 8.9186 (10) Å	T = 273 K
β = 114.103 (4)°	Plate, colourless
V = 1216.2 (2) Å^3	0.35 × 0.24 × 0.18 mm
Z = 4

Data collection

Bruker APEX II CCD diffractometer	2115 independent reflections
Radiation source: fine-focus sealed tube	1303 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
φ and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −9→9
Tmin = 0.975, Tmax = 0.986	k = −21→21
12849 measured reflections	l = −10→10

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)] = 0.064	H-atom parameters constrained
wR(F^2) = 0.242	w = 1/[σ^2(Fo^2) + (0.12P)^2 + 0.7798P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
2115 reflections	Δρmax = 0.21 e Å^−3
157 parameters	Δρmin = −0.20 e Å^−3
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.010 (4)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) 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
O1	0.7193 (3)	0.17283 (14)	1.0078 (4)	0.0955 (10)
H1	0.6678	0.2127	0.9949	0.143*
O2	0.6970 (3)	0.31456 (13)	0.9929 (4)	0.0975 (11)
C1	0.8678 (4)	0.18261 (17)	1.0027 (5)	0.0675 (10)
C2	0.9580 (5)	0.12019 (19)	1.0045 (5)	0.0812 (11)
H2	0.9105	0.0737	1.0069	0.097*
C3	1.1103 (5)	0.1267 (2)	1.0029 (5)	0.0811 (11)
H3	1.1754	0.0844	1.0044	0.097*
C4	1.1785 (4)	0.1956 (2)	0.9990 (5)	0.0738 (11)
C5	1.0873 (4)	0.25743 (18)	0.9949 (5)	0.0677 (10)
H5	1.1355	0.3036	0.9909	0.081*
C6	0.9320 (4)	0.25309 (16)	0.9965 (4)	0.0578 (8)
C7	1.3490 (5)	0.2031 (3)	1.0001 (7)	0.1133 (18)
H7A	1.4366	0.1904	1.1068	0.170*
H7B	1.3663	0.2535	0.9749	0.170*
H7C	1.3596	0.1706	0.9194	0.170*
C8	0.8332 (4)	0.31987 (17)	0.9903 (5)	0.0662 (10)
C9	0.9037 (4)	0.39513 (18)	0.9815 (5)	0.0758 (11)
H9A	1.0025	0.4045	1.0857	0.091*
H9B	0.9504	0.3937	0.8980	0.091*
C10	0.7835 (4)	0.45875 (17)	0.9461 (5)	0.0658 (10)
C11	0.6748 (5)	0.4736 (2)	0.7773 (6)	0.0851 (12)
H11	0.6796	0.4434	0.6947	0.102*
C12	0.5657 (6)	0.5323 (2)	0.7409 (6)	0.0960 (13)
H12	0.4928	0.5438	0.6326	0.115*
C13	0.5649 (5)	0.5762 (2)	0.8734 (6)	0.0826 (12)
H13	0.4887	0.6167	0.8477	0.099*
C14	0.6721 (5)	0.5627 (2)	1.0419 (6)	0.0808 (12)
H14	0.6672	0.5932	1.1241	0.097*
C15	0.7813 (4)	0.50376 (19)	1.0775 (5)	0.0755 (11)
H15	0.8542	0.4924	1.1859	0.091*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0523 (14)	0.0696 (16)	0.172 (3)	−0.0098 (11)	0.0535 (18)	0.0088 (17)
O2	0.0493 (14)	0.0712 (16)	0.189 (3)	0.0004 (11)	0.0659 (18)	0.0089 (16)
C1	0.0467 (17)	0.0606 (19)	0.094 (3)	−0.0052 (14)	0.0273 (17)	0.0027 (17)
C2	0.063 (2)	0.057 (2)	0.126 (3)	−0.0018 (16)	0.040 (2)	0.0014 (19)
C3	0.061 (2)	0.064 (2)	0.120 (3)	0.0118 (16)	0.038 (2)	0.000 (2)
C4	0.0425 (17)	0.075 (2)	0.108 (3)	0.0081 (15)	0.0350 (19)	0.0017 (19)
C5	0.0421 (17)	0.0597 (19)	0.103 (3)	−0.0007 (13)	0.0312 (18)	0.0020 (17)
C6	0.0377 (15)	0.0555 (18)	0.081 (2)	−0.0021 (12)	0.0249 (15)	0.0018 (15)
C7	0.052 (2)	0.103 (3)	0.197 (5)	0.012 (2)	0.063 (3)	0.002 (3)
C8	0.0439 (17)	0.0604 (19)	0.099 (3)	−0.0028 (13)	0.0338 (18)	0.0030 (17)
C9	0.0464 (17)	0.060 (2)	0.125 (3)	0.0004 (14)	0.0383 (19)	0.0051 (19)
C10	0.0431 (16)	0.0513 (17)	0.104 (3)	−0.0018 (13)	0.0312 (18)	0.0016 (17)
C11	0.080 (3)	0.074 (2)	0.102 (3)	0.0155 (19)	0.038 (2)	−0.007 (2)
C12	0.083 (3)	0.083 (3)	0.106 (3)	0.024 (2)	0.022 (2)	0.003 (2)
C13	0.060 (2)	0.060 (2)	0.132 (4)	0.0069 (15)	0.044 (2)	0.005 (2)
C14	0.078 (3)	0.066 (2)	0.112 (3)	−0.0015 (18)	0.052 (3)	−0.010 (2)
C15	0.059 (2)	0.069 (2)	0.095 (3)	0.0006 (16)	0.0286 (19)	0.003 (2)

Geometric parameters (Å, º)

O1—C1	1.263 (4)	C7—H7C	0.9600
O1—H1	0.8200	C8—C9	1.491 (4)
O2—C8	1.144 (4)	C9—C10	1.466 (4)
C1—C2	1.347 (5)	C9—H9A	0.9700
C1—C6	1.386 (4)	C9—H9B	0.9700
C2—C3	1.274 (5)	C10—C11	1.429 (5)
C2—H2	0.9300	C10—C15	1.431 (5)
C3—C4	1.371 (5)	C11—C12	1.342 (5)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.338 (4)	C12—C13	1.425 (6)
C4—C7	1.417 (5)	C12—H12	0.9300
C5—C6	1.297 (4)	C13—C14	1.420 (6)
C5—H5	0.9300	C13—H13	0.9300
C6—C8	1.443 (4)	C14—C15	1.346 (5)
C7—H7A	0.9600	C14—H14	0.9300
C7—H7B	0.9600	C15—H15	0.9300
C1—O1—H1	109.5	O2—C8—C9	119.3 (3)
O1—C1—C2	115.4 (3)	C6—C8—C9	122.1 (3)
O1—C1—C6	121.7 (3)	C10—C9—C8	118.4 (3)
C2—C1—C6	123.0 (3)	C10—C9—H9A	107.7
C3—C2—C1	118.2 (3)	C8—C9—H9A	107.7
C3—C2—H2	120.9	C10—C9—H9B	107.7
C1—C2—H2	120.9	C8—C9—H9B	107.7
C2—C3—C4	120.3 (3)	H9A—C9—H9B	107.1
C2—C3—H3	119.9	C11—C10—C15	122.9 (3)
C4—C3—H3	119.9	C11—C10—C9	117.0 (3)
C5—C4—C3	121.3 (3)	C15—C10—C9	120.1 (3)
C5—C4—C7	118.2 (3)	C12—C11—C10	118.4 (4)
C3—C4—C7	120.5 (3)	C12—C11—H11	120.8
C6—C5—C4	120.2 (3)	C10—C11—H11	120.8
C6—C5—H5	119.9	C11—C12—C13	117.9 (4)
C4—C5—H5	119.9	C11—C12—H12	121.0
C5—C6—C1	117.1 (3)	C13—C12—H12	121.0
C5—C6—C8	120.0 (3)	C14—C13—C12	124.7 (3)
C1—C6—C8	122.9 (3)	C14—C13—H13	117.6
C4—C7—H7A	109.5	C12—C13—H13	117.6
C4—C7—H7B	109.5	C15—C14—C13	117.0 (4)
H7A—C7—H7B	109.5	C15—C14—H14	121.5
C4—C7—H7C	109.5	C13—C14—H14	121.5
H7A—C7—H7C	109.5	C14—C15—C10	119.1 (4)
H7B—C7—H7C	109.5	C14—C15—H15	120.5
O2—C8—C6	118.6 (3)	C10—C15—H15	120.5
O1—C1—C2—C3	−178.7 (4)	C5—C6—C8—C9	0.1 (6)
C6—C1—C2—C3	1.1 (7)	C1—C6—C8—C9	−179.2 (3)
C1—C2—C3—C4	−0.2 (7)	O2—C8—C9—C10	−11.1 (6)
C2—C3—C4—C5	−0.8 (7)	C6—C8—C9—C10	169.2 (3)
C2—C3—C4—C7	178.9 (4)	C8—C9—C10—C11	−83.9 (4)
C3—C4—C5—C6	0.8 (6)	C8—C9—C10—C15	97.4 (4)
C7—C4—C5—C6	−178.9 (4)	C15—C10—C11—C12	−0.2 (6)
C4—C5—C6—C1	0.1 (6)	C9—C10—C11—C12	−178.9 (4)
C4—C5—C6—C8	−179.3 (4)	C10—C11—C12—C13	0.0 (6)
O1—C1—C6—C5	178.7 (4)	C11—C12—C13—C14	0.3 (7)
C2—C1—C6—C5	−1.1 (6)	C12—C13—C14—C15	−0.3 (6)
O1—C1—C6—C8	−1.9 (6)	C13—C14—C15—C10	0.1 (5)
C2—C1—C6—C8	178.3 (4)	C11—C10—C15—C14	0.2 (5)
C5—C6—C8—O2	−179.5 (4)	C9—C10—C15—C14	178.8 (3)
C1—C6—C8—O2	1.1 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.85	2.559 (3)	144
O1—H1···C7^i	0.82	2.67	3.093 (4)	114

Symmetry code: (i) x−1, y, z.