(2-Hy-droxy-4-meth-oxy-phen-yl)(2-hy-droxy-phen-yl)methanone.

The title compound, C(14)H(12)O(4), is an asymmetric substitution product of benzophenone. Both hy-droxy groups are orientated towards the O atom of the keto group. Intra-molecular as well as inter-molecular O-H⋯O hydrogen bonds can be observed in the crystal structure, with the latter connecting the mol-ecules into chains along the crystallographic b axis. C-H⋯O contacts [C⋯O = 3.3297 (18) Å] are also apparent. The closest centroid-centroid distance between two aromatic systems is 4.9186 (9) 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 the crystal structure of bis­(2-hy­droxy­phen­yl)methanone, see: Betz et al. (2011 ▶). For details on graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶). For a comparison of the thermodynamic stability of coordination compounds containing chelate ligands as opposed to monodentate ligands, see: Gade (1998 ▶).

Experimental

Crystal data

C14H12O4

M = 244.24

Orthorhombic,

a = 4.8582 (2) Å

b = 14.0236 (5) Å

c = 16.8636 (5) Å

V = 1148.91 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 200 K

0.48 × 0.14 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer

6314 measured reflections

1683 independent reflections

1484 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.083

S = 1.07

1683 reflections

166 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.17 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/S1600536811030042/lw2071sup1.cif

Supplementary material file. DOI: 10.1107/S1600536811030042/lw2071Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811030042/lw2071Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536811030042/lw2071Isup4.cml

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

C14H12O4	F(000) = 512
Mr = 244.24	Dx = 1.412 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4306 reflections
a = 4.8582 (2) Å	θ = 2.8–28.2°
b = 14.0236 (5) Å	µ = 0.10 mm−1
c = 16.8636 (5) Å	T = 200 K
V = 1148.91 (7) Å3	Platelet, yellow
Z = 4	0.48 × 0.14 × 0.05 mm

Bruker APEXII CCD diffractometer	1484 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
graphite	θmax = 28.3°, θmin = 1.9°
φ and ω scans	h = −4→6
6314 measured reflections	k = −18→17
1683 independent reflections	l = −21→22

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0509P)2 + 0.0857P] where P = (Fo2 + 2Fc2)/3
1683 reflections	(Δ/σ)max < 0.001
166 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

Refinement. Due to the absence of a strong anomalous scatterer, the Flack parameter is meaningless. Thus, Friedel opposites (1966 pairs) have been merged and the item was removed from the CIF.

	x	y	z	Uiso*/Ueq
O1	1.0688 (3)	−0.07918 (7)	0.34393 (6)	0.0382 (3)
O2	0.6572 (3)	−0.06852 (7)	0.24525 (6)	0.0374 (3)
H2	0.7719	−0.0968	0.2741	0.056*
O3	1.4961 (3)	−0.08333 (8)	0.43931 (7)	0.0390 (3)
H3	1.4061	−0.1013	0.3995	0.058*
O4	0.4289 (3)	0.24323 (8)	0.15520 (6)	0.0405 (3)
C1	1.0352 (3)	0.00668 (10)	0.36067 (8)	0.0288 (3)
C2	0.2546 (5)	0.20454 (13)	0.09489 (11)	0.0447 (5)
H2A	0.3649	0.1660	0.0583	0.067*
H2B	0.1664	0.2567	0.0657	0.067*
H2C	0.1130	0.1644	0.1194	0.067*
C11	0.8770 (3)	0.06797 (10)	0.30686 (8)	0.0273 (3)
C12	0.6941 (3)	0.02686 (10)	0.25159 (8)	0.0279 (3)
C13	0.5372 (4)	0.08324 (11)	0.20056 (8)	0.0296 (3)
H13	0.4108	0.0546	0.1648	0.036*
C14	0.5676 (4)	0.18145 (10)	0.20262 (8)	0.0309 (3)
C15	0.7562 (4)	0.22409 (10)	0.25446 (8)	0.0335 (4)
H15	0.7797	0.2913	0.2545	0.040*
C16	0.9063 (4)	0.16846 (10)	0.30496 (8)	0.0309 (3)
H16	1.0341	0.1980	0.3398	0.037*
C21	1.1541 (4)	0.04328 (10)	0.43571 (8)	0.0275 (3)
C22	1.3752 (4)	−0.00534 (10)	0.47108 (9)	0.0297 (3)
C23	1.4840 (4)	0.02689 (11)	0.54312 (9)	0.0344 (4)
H23	1.6380	−0.0046	0.5659	0.041*
C24	1.3687 (4)	0.10414 (12)	0.58103 (9)	0.0373 (4)
H24	1.4441	0.1256	0.6298	0.045*
C25	1.1439 (4)	0.15086 (11)	0.54881 (9)	0.0355 (4)
H25	1.0621	0.2030	0.5760	0.043*
C26	1.0397 (4)	0.12097 (10)	0.47670 (8)	0.0310 (3)
H26	0.8872	0.1537	0.4543	0.037*

	U11	U22	U33	U12	U13	U23
O1	0.0427 (7)	0.0264 (5)	0.0456 (6)	0.0066 (6)	−0.0057 (6)	−0.0090 (4)
O2	0.0490 (7)	0.0230 (5)	0.0403 (5)	−0.0041 (5)	−0.0070 (6)	−0.0036 (4)
O3	0.0417 (7)	0.0346 (6)	0.0406 (6)	0.0111 (6)	−0.0018 (6)	−0.0034 (5)
O4	0.0549 (8)	0.0284 (5)	0.0380 (5)	−0.0066 (6)	−0.0164 (7)	0.0015 (4)
C1	0.0276 (8)	0.0267 (6)	0.0322 (6)	−0.0003 (6)	0.0032 (7)	−0.0035 (5)
C2	0.0554 (12)	0.0360 (8)	0.0428 (8)	−0.0058 (9)	−0.0199 (10)	−0.0001 (7)
C11	0.0292 (8)	0.0252 (7)	0.0275 (6)	−0.0020 (7)	0.0037 (7)	−0.0036 (5)
C12	0.0318 (8)	0.0246 (7)	0.0272 (6)	−0.0045 (6)	0.0057 (7)	−0.0044 (5)
C13	0.0323 (8)	0.0286 (7)	0.0279 (6)	−0.0055 (7)	−0.0010 (7)	−0.0035 (5)
C14	0.0367 (9)	0.0300 (7)	0.0260 (6)	−0.0027 (7)	−0.0003 (8)	0.0006 (5)
C15	0.0449 (9)	0.0231 (6)	0.0324 (7)	−0.0090 (7)	−0.0045 (9)	0.0002 (5)
C16	0.0370 (9)	0.0260 (7)	0.0298 (6)	−0.0080 (7)	−0.0016 (8)	−0.0024 (5)
C21	0.0302 (8)	0.0234 (6)	0.0289 (6)	−0.0021 (6)	0.0037 (7)	0.0008 (5)
C22	0.0324 (8)	0.0254 (7)	0.0313 (6)	−0.0024 (7)	0.0057 (7)	0.0026 (5)
C23	0.0356 (9)	0.0337 (8)	0.0338 (7)	−0.0041 (7)	−0.0028 (8)	0.0057 (6)
C24	0.0470 (10)	0.0348 (8)	0.0300 (7)	−0.0118 (8)	−0.0009 (8)	−0.0011 (6)
C25	0.0436 (10)	0.0285 (7)	0.0343 (7)	−0.0038 (7)	0.0063 (8)	−0.0059 (6)
C26	0.0343 (9)	0.0258 (7)	0.0329 (7)	−0.0011 (7)	0.0022 (7)	−0.0007 (5)

O1—C1	1.2475 (18)	C13—H13	0.9500
O2—C12	1.3537 (16)	C14—C15	1.401 (2)
O2—H2	0.8400	C15—C16	1.366 (2)
O3—C22	1.3522 (19)	C15—H15	0.9500
O3—H3	0.8400	C16—H16	0.9500
O4—C14	1.3578 (19)	C21—C26	1.405 (2)
O4—C2	1.430 (2)	C21—C22	1.405 (2)
C1—C11	1.467 (2)	C22—C23	1.400 (2)
C1—C21	1.483 (2)	C23—C24	1.377 (2)
C2—H2A	0.9800	C23—H23	0.9500
C2—H2B	0.9800	C24—C25	1.384 (3)
C2—H2C	0.9800	C24—H24	0.9500
C11—C12	1.411 (2)	C25—C26	1.382 (2)
C11—C16	1.417 (2)	C25—H25	0.9500
C12—C13	1.395 (2)	C26—H26	0.9500
C13—C14	1.386 (2)
C12—O2—H2	109.5	C16—C15—C14	119.64 (13)
C22—O3—H3	109.5	C16—C15—H15	120.2
C14—O4—C2	118.06 (12)	C14—C15—H15	120.2
O1—C1—C11	119.60 (13)	C15—C16—C11	121.91 (15)
O1—C1—C21	118.44 (14)	C15—C16—H16	119.0
C11—C1—C21	121.95 (12)	C11—C16—H16	119.0
O4—C2—H2A	109.5	C26—C21—C22	118.02 (13)
O4—C2—H2B	109.5	C26—C21—C1	122.29 (15)
H2A—C2—H2B	109.5	C22—C21—C1	119.48 (13)
O4—C2—H2C	109.5	O3—C22—C23	116.15 (15)
H2A—C2—H2C	109.5	O3—C22—C21	123.81 (13)
H2B—C2—H2C	109.5	C23—C22—C21	120.04 (14)
C12—C11—C16	117.06 (14)	C24—C23—C22	120.20 (17)
C12—C11—C1	119.94 (12)	C24—C23—H23	119.9
C16—C11—C1	122.95 (14)	C22—C23—H23	119.9
O2—C12—C13	116.03 (13)	C23—C24—C25	120.74 (15)
O2—C12—C11	122.64 (13)	C23—C24—H24	119.6
C13—C12—C11	121.33 (13)	C25—C24—H24	119.6
C14—C13—C12	119.32 (14)	C26—C25—C24	119.38 (15)
C14—C13—H13	120.3	C26—C25—H25	120.3
C12—C13—H13	120.3	C24—C25—H25	120.3
O4—C14—C13	124.52 (14)	C25—C26—C21	121.54 (16)
O4—C14—C15	114.82 (13)	C25—C26—H26	119.2
C13—C14—C15	120.64 (15)	C21—C26—H26	119.2
O1—C1—C11—C12	20.0 (2)	C12—C11—C16—C15	2.8 (2)
C21—C1—C11—C12	−159.02 (14)	C1—C11—C16—C15	−179.82 (15)
O1—C1—C11—C16	−157.31 (16)	O1—C1—C21—C26	−152.15 (16)
C21—C1—C11—C16	23.7 (2)	C11—C1—C21—C26	26.9 (2)
C16—C11—C12—O2	177.13 (15)	O1—C1—C21—C22	22.6 (2)
C1—C11—C12—O2	−0.3 (2)	C11—C1—C21—C22	−158.41 (14)
C16—C11—C12—C13	−3.7 (2)	C26—C21—C22—O3	177.31 (15)
C1—C11—C12—C13	178.86 (14)	C1—C21—C22—O3	2.4 (2)
O2—C12—C13—C14	−178.84 (15)	C26—C21—C22—C23	−3.2 (2)
C11—C12—C13—C14	1.9 (2)	C1—C21—C22—C23	−178.13 (14)
C2—O4—C14—C13	−4.9 (2)	O3—C22—C23—C24	−178.06 (15)
C2—O4—C14—C15	173.44 (16)	C21—C22—C23—C24	2.4 (2)
C12—C13—C14—O4	179.11 (14)	C22—C23—C24—C25	0.1 (3)
C12—C13—C14—C15	0.9 (2)	C23—C24—C25—C26	−1.8 (3)
O4—C14—C15—C16	179.84 (15)	C24—C25—C26—C21	0.9 (2)
C13—C14—C15—C16	−1.8 (3)	C22—C21—C26—C25	1.6 (2)
C14—C15—C16—C11	−0.1 (3)	C1—C21—C26—C25	176.35 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.84	1.88	2.6058 (17)	144
O3—H3···O1	0.84	1.91	2.6267 (17)	142
O3—H3···O4i	0.84	2.50	2.9306 (15)	113
C15—H15···O1ii	0.95	2.57	3.3297 (18)	137

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	2.6058 (17)	144
O3—H3⋯O1	0.84	1.91	2.6267 (17)	142
O3—H3⋯O4i	0.84	2.50	2.9306 (15)	113
C15—H15⋯O1ii	0.95	2.57	3.3297 (18)	137

Symmetry codes: (i) ; (ii) .