Methyl 2-(4-hy­droxy­benzo­yl)benzoate

Abstract

In the title compound, C₁₅H₁₂O₄, the dihedral angle between the benzene rings is 64.0 (6)°. In the crystal, mol­ecules are linked by O—H⋯O hydrogen bonds, forming C(8) chains propagating in [10] and the packing is reinforced by weak C—H⋯O inter­actions.

Related literature

For background to benzophenone derivatives, see: Sieroń et al. (2004) ▶. For related structures, see: Cox et al. (2008 ▶); Jasinski et al. (2009 ▶). For reference bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

• C₁₅H₁₂O₄

• M _r = 256.25

• Monoclinic,

• a = 8.9017 (12) Å

• b = 13.9940 (17) Å

• c = 10.0473 (12) Å

• β = 94.687 (12)°

• V = 1247.4 (3) ų

• Z = 4

• Mo Kα radiation

• μ = 0.10 mm⁻¹

• T = 173 K

• 0.38 × 0.32 × 0.24 mm

Data collection

• Oxford Diffraction Xcalibur Eos Gemini diffractometer

• Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T _min = 0.963, T _max = 0.977

• 11331 measured reflections

• 3231 independent reflections

• 2722 reflections with I > 2σ(I)

• R _int = 0.020

Refinement

• R[F ² > 2σ(F ²)] = 0.042

• wR(F ²) = 0.117

• S = 1.02

• 3231 reflections

• 177 parameters

• 1 restraint

• H atoms treated by a mixture of independent and constrained refinement

• Δρ_max = 0.25 e Å⁻³

• Δρ_min = −0.18 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Supplementary material file. DOI: 10.1107/S1600536811026651/hb5942Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4O⋯O3i	0.85 (1)	1.88 (2)	2.7310 (14)	173 (2)
C12—H12A⋯O2i	0.95	2.50	3.4333 (15)	167

Symmetry code: (i) .

supplementary crystallographic information

Comment

The title compound is a starting material for the synthesis of pitofenone, which is an antispasmodic. More generally, benzophenone derivatives have many applications in organic chemistry (Sieroń et al., 2004). The crystal structures of some substituted benzophenones (Cox et al., 2008) and 2-amino-5-nitrophenyl 2-chlorophenyl ketone (Jasinski et al., 2009) have been reported. In view of the importance of the title compound, this paper reports the crystal structure of (I), C₁₅H₁₂O₄.

In the title compound, C₁₅H₁₂O₄, the dihedral angle between the mean planes of the two benzene rings is 64.0 (6)° (Fig. 1). Bond distances are in normal ranges (Allen et al., 1987). Crystal packing is stabilized by O—H···O hydrogen bonds and weak C—H···O intermolecular interactions (Table 1, Fig. 2).

Experimental

The title compound was obtained as a gift sample from R. L. Fine Chem, Bengaluru, india. Colourless blocks were grown from methanol solution (430-433 K).

Refinement

The O–H atom was located by Fourier analysis and refined isotropically with DFIX = 0.84Å. All of the remaining H atoms were placed in their calculated positions and then refined using the riding model with Atom–H lengths of 0.95Å (CH) or 0.98Å (CH₃). Isotropic displacement parameters for these atoms were set to 1.18-1.20 (CH) or 1.51 (CH₃) times U_eq of the parent atom.

Figures

Fig. 1.

Molecular structure of the title compound showing 50% probability displacement ellipsoids.

Fig. 2.

Packing diagram of the title compound viewed down the c axis. Dashed lines represent O—H···O hydrogen bonds.

Crystal data

C15H12O4	F(000) = 536
Mr = 256.25	Dx = 1.364 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4807 reflections
a = 8.9017 (12) Å	θ = 3.3–32.3°
b = 13.9940 (17) Å	µ = 0.10 mm−1
c = 10.0473 (12) Å	T = 173 K
β = 94.687 (12)°	Block, colorless
V = 1247.4 (3) Å3	0.38 × 0.32 × 0.24 mm
Z = 4

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer	3231 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2722 reflections with I > 2σ(I)
graphite	Rint = 0.020
Detector resolution: 16.1500 pixels mm-1	θmax = 28.7°, θmin = 3.3°
ω scans	h = −11→12
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −18→18
Tmin = 0.963, Tmax = 0.977	l = −12→13
11331 measured reflections

Refinement

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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.117	w = 1/[σ2(Fo2) + (0.0567P)2 + 0.3281P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
3231 reflections	Δρmax = 0.25 e Å−3
177 parameters	Δρmin = −0.18 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.059 (4)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.67772 (14)	0.53971 (7)	1.02990 (9)	0.0554 (3)
O2	0.65842 (11)	0.66691 (6)	0.89536 (10)	0.0444 (2)
O3	0.46662 (10)	0.59366 (8)	0.66899 (10)	0.0467 (3)
O4	0.67624 (12)	0.86689 (8)	0.21951 (11)	0.0538 (3)
H4O	0.7691 (17)	0.8749 (14)	0.2078 (19)	0.065*
C1	0.6277 (3)	0.59825 (13)	1.13629 (15)	0.0679 (5)
H1A	0.6325	0.5611	1.2192	0.102*
H1B	0.5236	0.6189	1.1131	0.102*
H1C	0.6930	0.6545	1.1487	0.102*
C2	0.68941 (13)	0.58440 (9)	0.91453 (12)	0.0353 (3)
C3	0.75070 (13)	0.52066 (8)	0.81331 (12)	0.0339 (3)
C4	0.85127 (16)	0.44807 (10)	0.85257 (14)	0.0452 (3)
H4A	0.8748	0.4357	0.9449	0.054*
C5	0.91727 (18)	0.39370 (11)	0.75845 (17)	0.0531 (4)
H5A	0.9850	0.3437	0.7862	0.064*
C6	0.88503 (17)	0.41180 (10)	0.62450 (16)	0.0494 (3)
H6A	0.9308	0.3745	0.5599	0.059*
C7	0.78597 (15)	0.48435 (9)	0.58380 (13)	0.0404 (3)
H7A	0.7654	0.4972	0.4913	0.048*
C8	0.71643 (12)	0.53855 (8)	0.67704 (11)	0.0322 (2)
C9	0.59158 (13)	0.60509 (8)	0.62820 (11)	0.0326 (2)
C10	0.61847 (12)	0.67596 (8)	0.52514 (11)	0.0308 (2)
C11	0.76378 (12)	0.70441 (8)	0.49875 (12)	0.0331 (3)
H11A	0.8483	0.6784	0.5502	0.040*
C12	0.78631 (13)	0.76950 (9)	0.39946 (12)	0.0353 (3)
H12A	0.8855	0.7890	0.3835	0.042*
C13	0.66243 (14)	0.80656 (9)	0.32274 (12)	0.0359 (3)
C14	0.51685 (13)	0.78068 (9)	0.34968 (13)	0.0384 (3)
H14A	0.4325	0.8073	0.2987	0.046*
C15	0.49546 (13)	0.71679 (9)	0.44985 (12)	0.0352 (3)
H15A	0.3959	0.7000	0.4684	0.042*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
O1	0.0885 (8)	0.0476 (6)	0.0317 (5)	0.0005 (5)	0.0142 (5)	0.0028 (4)
O2	0.0508 (5)	0.0381 (5)	0.0459 (5)	0.0019 (4)	0.0124 (4)	0.0004 (4)
O3	0.0334 (5)	0.0645 (6)	0.0436 (5)	0.0006 (4)	0.0112 (4)	0.0083 (4)
O4	0.0446 (5)	0.0645 (7)	0.0533 (6)	0.0042 (5)	0.0097 (5)	0.0255 (5)
C1	0.1059 (15)	0.0657 (10)	0.0344 (7)	−0.0035 (10)	0.0198 (8)	−0.0063 (7)
C2	0.0359 (6)	0.0384 (6)	0.0315 (6)	−0.0050 (5)	0.0029 (4)	0.0014 (4)
C3	0.0351 (6)	0.0321 (5)	0.0349 (6)	−0.0029 (4)	0.0046 (4)	0.0023 (4)
C4	0.0487 (7)	0.0425 (7)	0.0443 (7)	0.0041 (5)	0.0037 (6)	0.0103 (5)
C5	0.0536 (8)	0.0420 (7)	0.0647 (9)	0.0140 (6)	0.0101 (7)	0.0088 (6)
C6	0.0512 (8)	0.0415 (7)	0.0572 (9)	0.0084 (6)	0.0144 (6)	−0.0060 (6)
C7	0.0430 (7)	0.0410 (6)	0.0379 (6)	0.0008 (5)	0.0081 (5)	−0.0042 (5)
C8	0.0318 (5)	0.0317 (5)	0.0337 (6)	−0.0026 (4)	0.0054 (4)	0.0004 (4)
C9	0.0308 (5)	0.0383 (6)	0.0289 (5)	−0.0003 (4)	0.0041 (4)	−0.0033 (4)
C10	0.0287 (5)	0.0350 (6)	0.0289 (5)	0.0018 (4)	0.0036 (4)	−0.0028 (4)
C11	0.0274 (5)	0.0398 (6)	0.0317 (5)	0.0021 (4)	0.0005 (4)	−0.0015 (4)
C12	0.0286 (5)	0.0408 (6)	0.0368 (6)	−0.0018 (4)	0.0056 (4)	−0.0004 (5)
C13	0.0376 (6)	0.0374 (6)	0.0335 (6)	0.0036 (5)	0.0066 (5)	0.0019 (5)
C14	0.0305 (5)	0.0470 (7)	0.0375 (6)	0.0081 (5)	0.0015 (4)	0.0045 (5)
C15	0.0257 (5)	0.0438 (6)	0.0365 (6)	0.0019 (4)	0.0043 (4)	−0.0001 (5)

Geometric parameters (Å, °)

O1—C2	1.3286 (15)	C6—C7	1.3844 (19)
O1—C1	1.4458 (18)	C6—H6A	0.9500
O2—C2	1.1991 (15)	C7—C8	1.3895 (17)
O3—C9	1.2270 (14)	C7—H7A	0.9500
O4—C13	1.3508 (15)	C8—C9	1.5013 (16)
O4—H4O	0.852 (14)	C9—C10	1.4675 (16)
C1—H1A	0.9800	C10—C11	1.3993 (15)
C1—H1B	0.9800	C10—C15	1.4009 (16)
C1—H1C	0.9800	C11—C12	1.3777 (17)
C2—C3	1.4894 (17)	C11—H11A	0.9500
C3—C4	1.3896 (18)	C12—C13	1.3930 (17)
C3—C8	1.4007 (16)	C12—H12A	0.9500
C4—C5	1.382 (2)	C13—C14	1.3932 (17)
C4—H4A	0.9500	C14—C15	1.3711 (17)
C5—C6	1.377 (2)	C14—H14A	0.9500
C5—H5A	0.9500	C15—H15A	0.9500
C2—O1—C1	115.42 (12)	C8—C7—H7A	119.7
C13—O4—H4O	109.8 (13)	C7—C8—C3	119.21 (11)
O1—C1—H1A	109.5	C7—C8—C9	118.48 (10)
O1—C1—H1B	109.5	C3—C8—C9	121.78 (10)
H1A—C1—H1B	109.5	O3—C9—C10	121.90 (11)
O1—C1—H1C	109.5	O3—C9—C8	118.49 (11)
H1A—C1—H1C	109.5	C10—C9—C8	119.39 (10)
H1B—C1—H1C	109.5	C11—C10—C15	118.39 (10)
O2—C2—O1	124.05 (12)	C11—C10—C9	122.18 (10)
O2—C2—C3	124.01 (11)	C15—C10—C9	119.43 (10)
O1—C2—C3	111.90 (10)	C12—C11—C10	121.12 (10)
C4—C3—C8	119.47 (11)	C12—C11—H11A	119.4
C4—C3—C2	120.49 (11)	C10—C11—H11A	119.4
C8—C3—C2	119.85 (10)	C11—C12—C13	119.43 (11)
C5—C4—C3	120.55 (13)	C11—C12—H12A	120.3
C5—C4—H4A	119.7	C13—C12—H12A	120.3
C3—C4—H4A	119.7	O4—C13—C12	122.68 (11)
C6—C5—C4	120.09 (13)	O4—C13—C14	117.13 (11)
C6—C5—H5A	120.0	C12—C13—C14	120.18 (11)
C4—C5—H5A	120.0	C15—C14—C13	119.95 (11)
C5—C6—C7	120.04 (13)	C15—C14—H14A	120.0
C5—C6—H6A	120.0	C13—C14—H14A	120.0
C7—C6—H6A	120.0	C14—C15—C10	120.87 (10)
C6—C7—C8	120.61 (12)	C14—C15—H15A	119.6
C6—C7—H7A	119.7	C10—C15—H15A	119.6
C1—O1—C2—O2	−1.6 (2)	C3—C8—C9—O3	−51.01 (16)
C1—O1—C2—C3	176.40 (13)	C7—C8—C9—C10	−54.18 (15)
O2—C2—C3—C4	147.15 (13)	C3—C8—C9—C10	134.26 (12)
O1—C2—C3—C4	−30.85 (16)	O3—C9—C10—C11	165.69 (12)
O2—C2—C3—C8	−27.74 (18)	C8—C9—C10—C11	−19.76 (16)
O1—C2—C3—C8	154.27 (11)	O3—C9—C10—C15	−14.46 (17)
C8—C3—C4—C5	0.0 (2)	C8—C9—C10—C15	160.09 (11)
C2—C3—C4—C5	−174.93 (12)	C15—C10—C11—C12	−1.31 (17)
C3—C4—C5—C6	0.7 (2)	C9—C10—C11—C12	178.54 (11)
C4—C5—C6—C7	−0.2 (2)	C10—C11—C12—C13	−0.95 (18)
C5—C6—C7—C8	−1.0 (2)	C11—C12—C13—O4	−176.60 (12)
C6—C7—C8—C3	1.68 (19)	C11—C12—C13—C14	2.41 (18)
C6—C7—C8—C9	−170.10 (12)	O4—C13—C14—C15	177.49 (12)
C4—C3—C8—C7	−1.16 (17)	C12—C13—C14—C15	−1.58 (19)
C2—C3—C8—C7	173.77 (11)	C13—C14—C15—C10	−0.74 (19)
C4—C3—C8—C9	170.33 (11)	C11—C10—C15—C14	2.16 (17)
C2—C3—C8—C9	−14.73 (16)	C9—C10—C15—C14	−177.69 (11)
C7—C8—C9—O3	120.55 (13)

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4O···O3i	0.85 (1)	1.88 (2)	2.7310 (14)	173.(2)
C12—H12A···O2i	0.95	2.50	3.4333 (15)	167

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