Bis(2-hy-droxy-phen-yl)methanone.

In the title compound, C(13)H(10)O(3), a benzophenone derivative, the least-squares planes defined by the C atoms of the 2-hy-droxy-phenyl rings inter-sect at an angle of 45.49 (3)°. The substituents on the aromatic systems are both orientated towards the central O atom. Intra- as well as inter-molecular O-H⋯O hydrogen bonds are observed, the latter giving rise to the formation of centrosymmetric dimers. The closest centroid-centroid distance between two π-systems is 3.7934 (7) Å.

Related literature

For the crystal structure of benzophenone, see: Lobanova (1968 ▶); Kutzke et al. (2000 ▶); Fleischer et al. (1968 ▶); Bernstein et al. (2002 ▶); Moncol & Coppens (2004 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶). Chelate ligands have found widespread use in coordination chemistry due to the enhanced thermodynamic stability of the resultant coordination compounds in relation to those exclusively applying comparable monodentate ligands, see: Gade (1998 ▶).

Experimental

Crystal data

C13H10O3

M = 214.21

Monoclinic,

a = 7.7371 (2) Å

b = 12.2169 (4) Å

c = 11.3419 (3) Å

β = 110.610 (2)°

V = 1003.46 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 200 K

0.24 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer

9306 measured reflections

2483 independent reflections

1939 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.106

S = 1.05

2483 reflections

147 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811025438/im2302sup1.cif

Supplementary material file. DOI: 10.1107/S1600536811025438/im2302Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811025438/im2302Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536811025438/im2302Isup4.cml

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

C13H10O3	F(000) = 448
Mr = 214.21	Dx = 1.418 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4455 reflections
a = 7.7371 (2) Å	θ = 2.5–28.3°
b = 12.2169 (4) Å	µ = 0.10 mm−1
c = 11.3419 (3) Å	T = 200 K
β = 110.610 (2)°	Platelet, colourless
V = 1003.46 (5) Å3	0.24 × 0.20 × 0.18 mm
Z = 4

Bruker APEXII CCD diffractometer	1939 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
graphite	θmax = 28.3°, θmin = 2.5°
φ and ω scans	h = −9→10
9306 measured reflections	k = −15→16
2483 independent reflections	l = −15→15

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0563P)2 + 0.1145P] where P = (Fo2 + 2Fc2)/3
2483 reflections	(Δ/σ)max < 0.001
147 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.97092 (13)	0.09617 (6)	0.08169 (7)	0.0405 (2)
O2	0.78137 (13)	0.09971 (7)	−0.15911 (8)	0.0407 (2)
H2	0.8528	0.0719	−0.0919	0.061*
O3	1.09865 (13)	0.09673 (6)	0.33247 (8)	0.0407 (2)
H3	1.0534	0.0664	0.2617	0.061*
C1	0.94988 (15)	0.19703 (8)	0.08687 (9)	0.0271 (2)
C11	0.80678 (14)	0.25299 (8)	−0.01695 (9)	0.0255 (2)
C12	0.73030 (15)	0.20048 (9)	−0.13533 (10)	0.0294 (2)
C13	0.59669 (16)	0.25366 (10)	−0.23411 (10)	0.0348 (3)
H13	0.5499	0.2199	−0.3146	0.042*
C14	0.53150 (16)	0.35473 (10)	−0.21639 (11)	0.0358 (3)
H14	0.4388	0.3896	−0.2844	0.043*
C15	0.60019 (16)	0.40645 (9)	−0.09954 (10)	0.0334 (3)
H15	0.5537	0.4759	−0.0876	0.040*
C16	0.73588 (15)	0.35604 (9)	−0.00167 (10)	0.0287 (2)
H16	0.7827	0.3915	0.0779	0.034*
C21	1.06958 (14)	0.25691 (8)	0.19946 (9)	0.0253 (2)
C22	1.13591 (15)	0.20282 (9)	0.31684 (9)	0.0283 (2)
C23	1.24280 (15)	0.25933 (10)	0.42392 (9)	0.0340 (3)
H23	1.2807	0.2242	0.5037	0.041*
C24	1.29406 (17)	0.36599 (10)	0.41490 (11)	0.0372 (3)
H24	1.3674	0.4039	0.4887	0.045*
C25	1.23981 (16)	0.41868 (9)	0.29931 (11)	0.0341 (3)
H25	1.2798	0.4913	0.2933	0.041*
C26	1.12737 (15)	0.36495 (8)	0.19308 (10)	0.0282 (2)
H26	1.0883	0.4017	0.1142	0.034*

	U11	U22	U33	U12	U13	U23
O1	0.0588 (6)	0.0236 (4)	0.0317 (4)	0.0033 (4)	0.0067 (4)	−0.0005 (3)
O2	0.0478 (5)	0.0359 (5)	0.0319 (4)	0.0011 (4)	0.0058 (4)	−0.0106 (3)
O3	0.0538 (6)	0.0312 (4)	0.0305 (4)	−0.0037 (4)	0.0068 (4)	0.0094 (3)
C1	0.0338 (6)	0.0232 (5)	0.0247 (5)	−0.0006 (4)	0.0107 (4)	0.0006 (4)
C11	0.0279 (5)	0.0258 (5)	0.0223 (5)	−0.0033 (4)	0.0081 (4)	0.0005 (4)
C12	0.0301 (5)	0.0315 (5)	0.0266 (5)	−0.0041 (4)	0.0101 (4)	−0.0028 (4)
C13	0.0319 (6)	0.0471 (7)	0.0217 (5)	−0.0048 (5)	0.0051 (4)	−0.0022 (5)
C14	0.0293 (6)	0.0478 (7)	0.0282 (5)	0.0025 (5)	0.0073 (5)	0.0099 (5)
C15	0.0340 (6)	0.0331 (6)	0.0341 (6)	0.0052 (5)	0.0131 (5)	0.0051 (5)
C16	0.0312 (5)	0.0296 (5)	0.0254 (5)	−0.0006 (4)	0.0099 (4)	0.0004 (4)
C21	0.0268 (5)	0.0258 (5)	0.0230 (5)	0.0023 (4)	0.0083 (4)	0.0012 (4)
C22	0.0290 (5)	0.0293 (5)	0.0264 (5)	0.0024 (4)	0.0097 (4)	0.0040 (4)
C23	0.0333 (6)	0.0448 (7)	0.0218 (5)	0.0014 (5)	0.0074 (5)	0.0038 (5)
C24	0.0355 (6)	0.0454 (7)	0.0279 (6)	−0.0065 (5)	0.0078 (5)	−0.0082 (5)
C25	0.0354 (6)	0.0313 (6)	0.0356 (6)	−0.0059 (5)	0.0125 (5)	−0.0042 (5)
C26	0.0304 (5)	0.0275 (5)	0.0269 (5)	0.0012 (4)	0.0101 (4)	0.0019 (4)

O1—C1	1.2470 (12)	C15—C16	1.3760 (15)
O2—C12	1.3489 (13)	C15—H15	0.9500
O2—H2	0.8400	C16—H16	0.9500
O3—C22	1.3530 (13)	C21—C26	1.4035 (14)
O3—H3	0.8400	C21—C22	1.4112 (13)
C1—C11	1.4703 (14)	C22—C23	1.3886 (15)
C1—C21	1.4802 (14)	C23—C24	1.3763 (16)
C11—C16	1.4081 (15)	C23—H23	0.9500
C11—C12	1.4161 (14)	C24—C25	1.3864 (16)
C12—C13	1.3894 (15)	C24—H24	0.9500
C13—C14	1.3750 (17)	C25—C26	1.3790 (15)
C13—H13	0.9500	C25—H25	0.9500
C14—C15	1.3936 (16)	C26—H26	0.9500
C14—H14	0.9500
C12—O2—H2	109.5	C15—C16—H16	119.3
C22—O3—H3	109.5	C11—C16—H16	119.3
O1—C1—C11	119.72 (9)	C26—C21—C22	118.19 (9)
O1—C1—C21	118.46 (9)	C26—C21—C1	122.29 (9)
C11—C1—C21	121.81 (9)	C22—C21—C1	119.46 (9)
C16—C11—C12	118.09 (9)	O3—C22—C23	116.77 (9)
C16—C11—C1	122.23 (9)	O3—C22—C21	123.28 (9)
C12—C11—C1	119.62 (9)	C23—C22—C21	119.94 (10)
O2—C12—C13	116.92 (9)	C24—C23—C22	120.28 (10)
O2—C12—C11	123.30 (10)	C24—C23—H23	119.9
C13—C12—C11	119.78 (10)	C22—C23—H23	119.9
C14—C13—C12	120.60 (10)	C23—C24—C25	120.71 (10)
C14—C13—H13	119.7	C23—C24—H24	119.6
C12—C13—H13	119.7	C25—C24—H24	119.6
C13—C14—C15	120.62 (10)	C26—C25—C24	119.54 (10)
C13—C14—H14	119.7	C26—C25—H25	120.2
C15—C14—H14	119.7	C24—C25—H25	120.2
C16—C15—C14	119.44 (11)	C25—C26—C21	121.14 (10)
C16—C15—H15	120.3	C25—C26—H26	119.4
C14—C15—H15	120.3	C21—C26—H26	119.4
C15—C16—C11	121.37 (10)
O1—C1—C11—C16	159.44 (10)	O1—C1—C21—C26	146.95 (11)
C21—C1—C11—C16	−19.72 (15)	C11—C1—C21—C26	−33.88 (15)
O1—C1—C11—C12	−17.66 (15)	O1—C1—C21—C22	−30.02 (14)
C21—C1—C11—C12	163.18 (10)	C11—C1—C21—C22	149.15 (10)
C16—C11—C12—O2	−176.94 (9)	C26—C21—C22—O3	−175.80 (10)
C1—C11—C12—O2	0.28 (16)	C1—C21—C22—O3	1.29 (16)
C16—C11—C12—C13	3.58 (15)	C26—C21—C22—C23	5.22 (15)
C1—C11—C12—C13	−179.20 (9)	C1—C21—C22—C23	−177.68 (9)
O2—C12—C13—C14	177.36 (10)	O3—C22—C23—C24	176.91 (10)
C11—C12—C13—C14	−3.13 (17)	C21—C22—C23—C24	−4.05 (17)
C12—C13—C14—C15	0.97 (17)	C22—C23—C24—C25	0.12 (18)
C13—C14—C15—C16	0.68 (17)	C23—C24—C25—C26	2.53 (18)
C14—C15—C16—C11	−0.13 (17)	C24—C25—C26—C21	−1.22 (17)
C12—C11—C16—C15	−1.98 (15)	C22—C21—C26—C25	−2.61 (16)
C1—C11—C16—C15	−179.12 (10)	C1—C21—C26—C25	−179.62 (10)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.84	1.88	2.6061 (11)	144
O2—H2···O1i	0.84	2.44	2.9976 (12)	124
O3—H3···O1	0.84	1.95	2.6623 (11)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1	0.84	1.88	2.6061 (11)	144
O2—H2⋯O1i	0.84	2.44	2.9976 (12)	124
O3—H3⋯O1	0.84	1.95	2.6623 (11)	142

Symmetry code: (i) .