1-(3,4-Dihydroxy-phen-yl)-2-(4-hydroxy-phen-yl)ethanone.

The title compound, C(14)H(12)O(4), is a deoxy-benzoin derivative in which the dihedral between the carbonyl group and the catechol unit is 5.99 (3)°. The dihedral angle between the two benzene rings is 60.26 (13)°. In the crystal structure, inter-molecular O-H⋯O hydrogen bonds connect mol-ecules, forming a two-dimensional network. In addition, weak inter-molecular C-H⋯O hydrogen bonds and C-H⋯π contacts further stabilize the crystal structure.

Related literature

For synthetic applications of deoxy­benzoin compounds, see: Xiao et al. (2007a ▶, 2008a ▶). For natural occurences of these compounds. see: Kiuchi et al. (1990 ▶); Niwa et al. (1999 ▶); Sanduja et al. (1985 ▶). For their biological activity, see: Papoutsi et al. (2007 ▶); Xiao et al. (2007b ▶, 2008b ▶); Parmar et al. (1996 ▶). For a related structure, see: Xiao & Xiao (2008c ▶).

Experimental

Crystal data

C14H12O4

M = 244.24

Triclinic,

a = 5.7073 (11) Å

b = 9.3464 (19) Å

c = 11.202 (2) Å

α = 100.112 (9)°

β = 94.792 (9)°

γ = 100.625 (9)°

V = 573.99 (19) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.970, T max = 0.980

3179 measured reflections

2214 independent reflections

1756 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.172

S = 1.06

2214 reflections

166 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.32 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809049393/lh2957sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049393/lh2957Isup2.hkl

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

C14H12O4	Z = 2
Mr = 244.24	F(000) = 256
Triclinic, P1	Dx = 1.413 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.7073 (11) Å	Cell parameters from 1785 reflections
b = 9.3464 (19) Å	θ = 2.0–26.0°
c = 11.202 (2) Å	µ = 0.10 mm−1
α = 100.112 (9)°	T = 296 K
β = 94.792 (9)°	Block, colorless
γ = 100.625 (9)°	0.30 × 0.20 × 0.20 mm
V = 573.99 (19) Å3

Bruker SMART APEX CCD diffractometer	2214 independent reflections
Radiation source: fine-focus sealed tube	1756 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→6
Tmin = 0.970, Tmax = 0.980	k = −11→6
3179 measured reflections	l = −13→13

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.172	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.1062P)2 + 0.1004P] where P = (Fo2 + 2Fc2)/3
2214 reflections	(Δ/σ)max < 0.001
166 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.0231 (3)	0.4370 (2)	0.17089 (17)	0.0357 (4)
C2	0.2221 (3)	0.4285 (2)	0.24884 (17)	0.0342 (4)
C3	0.2784 (3)	0.5201 (2)	0.36129 (17)	0.0357 (5)
H3	0.4123	0.5140	0.4120	0.043*
C4	0.1374 (3)	0.62287 (19)	0.40118 (17)	0.0335 (4)
C5	−0.0606 (3)	0.6309 (2)	0.32327 (18)	0.0364 (5)
H5	−0.1561	0.6986	0.3480	0.044*
C6	−0.1164 (3)	0.5392 (2)	0.20949 (18)	0.0382 (5)
H6	−0.2490	0.5460	0.1582	0.046*
C7	0.2107 (4)	0.7192 (2)	0.52317 (18)	0.0377 (5)
C8	0.0779 (4)	0.8423 (2)	0.56251 (19)	0.0434 (5)
H8A	0.0603	0.8942	0.4956	0.052*
H8B	−0.0821	0.7977	0.5769	0.052*
C9	0.1937 (3)	0.9545 (2)	0.67514 (18)	0.0376 (5)
C10	0.4194 (4)	1.0415 (2)	0.67929 (19)	0.0464 (5)
H10	0.5049	1.0265	0.6126	0.056*
C11	0.5210 (4)	1.1498 (2)	0.77965 (19)	0.0466 (5)
H11	0.6730	1.2070	0.7802	0.056*
C12	0.3970 (3)	1.1730 (2)	0.87899 (17)	0.0375 (5)
C13	0.1733 (4)	1.0874 (2)	0.8778 (2)	0.0497 (6)
H13	0.0887	1.1019	0.9449	0.060*
C14	0.0751 (4)	0.9795 (2)	0.7761 (2)	0.0497 (6)
H14	−0.0763	0.9220	0.7760	0.060*
O1	−0.0188 (3)	0.34464 (17)	0.06112 (13)	0.0505 (4)
H1	−0.1572	0.3388	0.0313	0.076*
O2	0.3534 (2)	0.32578 (15)	0.20545 (12)	0.0420 (4)
H2	0.4435	0.3133	0.2620	0.063*
O3	0.3760 (3)	0.70119 (18)	0.59031 (14)	0.0609 (5)
O4	0.5023 (3)	1.28604 (17)	0.97474 (14)	0.0507 (4)
H4	0.4249	1.2818	1.0329	0.076*

	U11	U22	U33	U12	U13	U23
C1	0.0337 (10)	0.0355 (9)	0.0340 (10)	0.0061 (7)	−0.0017 (7)	0.0002 (8)
C2	0.0314 (10)	0.0336 (9)	0.0374 (10)	0.0096 (7)	0.0032 (7)	0.0034 (8)
C3	0.0340 (10)	0.0344 (9)	0.0373 (10)	0.0113 (8)	−0.0047 (8)	0.0028 (8)
C4	0.0343 (10)	0.0291 (9)	0.0366 (10)	0.0096 (7)	−0.0001 (8)	0.0036 (7)
C5	0.0319 (10)	0.0337 (9)	0.0433 (11)	0.0123 (7)	0.0005 (8)	0.0028 (8)
C6	0.0317 (10)	0.0392 (10)	0.0412 (11)	0.0101 (8)	−0.0056 (8)	0.0027 (8)
C7	0.0404 (11)	0.0330 (9)	0.0402 (11)	0.0141 (8)	−0.0016 (8)	0.0045 (8)
C8	0.0404 (11)	0.0383 (10)	0.0479 (12)	0.0162 (8)	−0.0047 (9)	−0.0052 (9)
C9	0.0377 (11)	0.0328 (9)	0.0413 (11)	0.0149 (8)	−0.0002 (8)	−0.0011 (8)
C10	0.0429 (12)	0.0534 (12)	0.0379 (11)	0.0079 (9)	0.0099 (9)	−0.0047 (9)
C11	0.0358 (11)	0.0521 (12)	0.0443 (12)	0.0021 (9)	0.0057 (9)	−0.0040 (9)
C12	0.0379 (11)	0.0371 (10)	0.0345 (10)	0.0116 (8)	−0.0008 (8)	−0.0030 (8)
C13	0.0486 (13)	0.0489 (12)	0.0470 (13)	0.0061 (10)	0.0174 (10)	−0.0046 (10)
C14	0.0391 (12)	0.0420 (11)	0.0610 (14)	0.0010 (9)	0.0114 (10)	−0.0039 (10)
O1	0.0472 (9)	0.0560 (9)	0.0417 (9)	0.0205 (7)	−0.0100 (7)	−0.0116 (7)
O2	0.0402 (8)	0.0456 (8)	0.0390 (8)	0.0206 (6)	−0.0024 (6)	−0.0043 (6)
O3	0.0755 (12)	0.0577 (10)	0.0467 (9)	0.0401 (8)	−0.0243 (8)	−0.0110 (7)
O4	0.0450 (9)	0.0559 (9)	0.0415 (8)	0.0076 (7)	0.0011 (6)	−0.0119 (7)

C1—O1	1.348 (2)	C8—H8B	0.9700
C1—C6	1.388 (3)	C9—C14	1.373 (3)
C1—C2	1.396 (3)	C9—C10	1.383 (3)
C2—C3	1.369 (3)	C10—C11	1.378 (3)
C2—O2	1.372 (2)	C10—H10	0.9300
C3—C4	1.402 (3)	C11—C12	1.375 (3)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.390 (2)	C12—C13	1.374 (3)
C4—C7	1.479 (3)	C12—O4	1.374 (2)
C5—C6	1.382 (3)	C13—C14	1.382 (3)
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	C14—H14	0.9300
C7—O3	1.212 (2)	O1—H1	0.8200
C7—C8	1.514 (3)	O2—H2	0.8200
C8—C9	1.506 (3)	O4—H4	0.8200
C8—H8A	0.9700
O1—C1—C6	124.22 (17)	C9—C8—H8B	108.4
O1—C1—C2	116.86 (17)	C7—C8—H8B	108.4
C6—C1—C2	118.92 (17)	H8A—C8—H8B	107.4
C3—C2—O2	123.43 (16)	C14—C9—C10	117.12 (19)
C3—C2—C1	120.35 (17)	C14—C9—C8	121.34 (19)
O2—C2—C1	116.22 (16)	C10—C9—C8	121.47 (19)
C2—C3—C4	121.03 (16)	C11—C10—C9	121.7 (2)
C2—C3—H3	119.5	C11—C10—H10	119.1
C4—C3—H3	119.5	C9—C10—H10	119.1
C5—C4—C3	118.43 (17)	C12—C11—C10	119.8 (2)
C5—C4—C7	123.56 (16)	C12—C11—H11	120.1
C3—C4—C7	118.00 (16)	C10—C11—H11	120.1
C6—C5—C4	120.53 (17)	C13—C12—O4	122.75 (18)
C6—C5—H5	119.7	C13—C12—C11	119.75 (19)
C4—C5—H5	119.7	O4—C12—C11	117.47 (18)
C5—C6—C1	120.75 (17)	C12—C13—C14	119.4 (2)
C5—C6—H6	119.6	C12—C13—H13	120.3
C1—C6—H6	119.6	C14—C13—H13	120.3
O3—C7—C4	120.71 (17)	C9—C14—C13	122.2 (2)
O3—C7—C8	120.36 (18)	C9—C14—H14	118.9
C4—C7—C8	118.93 (15)	C13—C14—H14	118.9
C9—C8—C7	115.66 (16)	C1—O1—H1	109.5
C9—C8—H8A	108.4	C2—O2—H2	109.5
C7—C8—H8A	108.4	C12—O4—H4	109.5
O1—C1—C2—C3	179.11 (17)	C3—C4—C7—C8	173.33 (18)
C6—C1—C2—C3	−0.2 (3)	O3—C7—C8—C9	11.5 (3)
O1—C1—C2—O2	−0.5 (3)	C4—C7—C8—C9	−167.73 (17)
C6—C1—C2—O2	−179.76 (17)	C7—C8—C9—C14	−121.6 (2)
O2—C2—C3—C4	−179.83 (17)	C7—C8—C9—C10	61.4 (3)
C1—C2—C3—C4	0.6 (3)	C14—C9—C10—C11	−0.6 (3)
C2—C3—C4—C5	−0.6 (3)	C8—C9—C10—C11	176.50 (18)
C2—C3—C4—C7	−179.35 (16)	C9—C10—C11—C12	0.1 (3)
C3—C4—C5—C6	0.2 (3)	C10—C11—C12—C13	0.4 (3)
C7—C4—C5—C6	178.83 (17)	C10—C11—C12—O4	−177.56 (18)
C4—C5—C6—C1	0.3 (3)	O4—C12—C13—C14	177.42 (18)
O1—C1—C6—C5	−179.49 (18)	C11—C12—C13—C14	−0.5 (3)
C2—C1—C6—C5	−0.3 (3)	C10—C9—C14—C13	0.6 (3)
C5—C4—C7—O3	175.4 (2)	C8—C9—C14—C13	−176.54 (19)
C3—C4—C7—O3	−5.9 (3)	C12—C13—C14—C9	−0.1 (3)
C5—C4—C7—C8	−5.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4i	0.82	1.94	2.744 (2)	168
O2—H2···O3ii	0.82	1.91	2.7274 (19)	171
O4—H4···O2iii	0.82	2.00	2.772 (2)	158
C3—H3···O3ii	0.93	2.53	3.191 (2)	129
C11—H11···Cg1iv	0.93	2.85	3.635 (2)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4i	0.82	1.94	2.744 (2)	168
O2—H2⋯O3ii	0.82	1.91	2.7274 (19)	171
O4—H4⋯O2iii	0.82	2.00	2.772 (2)	158
C3—H3⋯O3ii	0.93	2.53	3.191 (2)	129
C11—H11⋯Cg1iv	0.93	2.85	3.635 (2)	143

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1 is the centroid of the C1–C6 ring.