(2,4-Dihy-droxy-6-meth-oxy-phen-yl)(3,5-dihy-droxy-phen-yl)methanone monohydrate.

The title benzophenone compound, C(14)H(12)O(6)·H(2)O, was isolated from the bark of Garcinia hombroniana Pierre (Guttiferae). The mol-ecule is twisted, the dihedral angle between the two benzene rings being 59.13 (7)°. The meth-oxy group is approximately coplanar with the attached benzene ring, with a C-O-C-C torsion angle of 1.91 (18)°. The water mol-ecule is disordered over two positions in a 0.555 (19):0.445 (19) ratio. An intra-molecular O-H⋯O hydrogen bond generates an S(6) ring motif. The crystal structure is stabilized by inter-molecular O-H⋯O hydrogen bonds. These inter-actions link the mol-ecules into sheets parallel to the ac plane. The sheets are stacked along the b axis by π-π inter-actions, with centroid-centroid distances of 3.6219 (7) Å. A weak O-H⋯π inter-action was also noted.

Related literature

For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For background to benzophenones and their bioactivity, see: Khanum et al. (2009 ▶); Pereira et al. (2010 ▶); Tzanova et al. (2009 ▶). For background to Guttiferae plants, see: Jayaprakasha et al. (2006 ▶); Mahabusarakum et al. (1983 ▶); Ngoupayo et al. (2009 ▶); Pereira et al. (2010 ▶); Phongpaichit et al. (1994 ▶); Smitinand (2001 ▶); Zadernowski et al. (2009 ▶); Zhang et al. (2010 ▶). For related structures, see: Betz et al. (2011 ▶); Li et al. (2010 ▶). For stability of the temperature controller used in the data collection, see Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C14H12O6·H2O

M = 294.25

Triclinic,

a = 7.7087 (1) Å

b = 8.4050 (1) Å

c = 11.2380 (1) Å

α = 82.401 (1)°

β = 75.570 (1)°

γ = 67.842 (1)°

V = 652.49 (1) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 100 K

0.42 × 0.33 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.951, T max = 0.988

19157 measured reflections

4696 independent reflections

4220 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.131

S = 1.17

4696 reflections

217 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.51 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811037913/tk2790sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037913/tk2790Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811037913/tk2790Isup3.cml

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

C14H12O6·H2O	Z = 2
Mr = 294.25	F(000) = 308
Triclinic, P1	Dx = 1.498 Mg m−3
Hall symbol: -P 1	Melting point = 516–519 K
a = 7.7087 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.4050 (1) Å	Cell parameters from 4696 reflections
c = 11.2380 (1) Å	θ = 1.9–32.5°
α = 82.401 (1)°	µ = 0.12 mm−1
β = 75.570 (1)°	T = 100 K
γ = 67.842 (1)°	Plate, yellow
V = 652.49 (1) Å3	0.42 × 0.33 × 0.10 mm

Bruker APEXII CCD area-detector diffractometer	4696 independent reflections
Radiation source: sealed tube	4220 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 32.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→11
Tmin = 0.951, Tmax = 0.988	k = −12→12
19157 measured reflections	l = −16→16

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	w = 1/[σ2(Fo2) + (0.038P)2 + 0.633P] where P = (Fo2 + 2Fc2)/3
4696 reflections	(Δ/σ)max = 0.001
217 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 120.0 (1) K.

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 > 2sigma(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	Occ. (<1)
O1	0.02024 (14)	0.10822 (14)	0.58801 (9)	0.01558 (19)
O2	0.18999 (14)	0.13186 (13)	0.36467 (9)	0.01292 (18)
H1O2	0.114 (4)	0.106 (4)	0.432 (3)	0.044 (7)*
O3	0.74976 (15)	0.27372 (15)	0.28766 (10)	0.0168 (2)
H1O3	0.757 (4)	0.250 (3)	0.215 (2)	0.032 (6)*
O4	0.40238 (14)	0.24500 (14)	0.69771 (9)	0.01396 (19)
O5	−0.23219 (17)	0.21024 (15)	1.05072 (9)	0.0191 (2)
H1O5	−0.247 (4)	0.123 (3)	1.035 (2)	0.036 (7)*
O6	−0.12705 (15)	0.70856 (13)	0.85592 (10)	0.01557 (19)
H1O6	−0.114 (4)	0.751 (4)	0.789 (3)	0.040 (7)*
C1	0.27991 (17)	0.20544 (16)	0.53565 (11)	0.0104 (2)
C2	0.31206 (17)	0.17912 (16)	0.40884 (11)	0.0106 (2)
C3	0.46478 (18)	0.20447 (17)	0.32314 (12)	0.0125 (2)
H3A	0.4796	0.1921	0.2380	0.015*
C4	0.59587 (18)	0.24845 (17)	0.36499 (12)	0.0121 (2)
C5	0.57783 (18)	0.26523 (17)	0.49021 (12)	0.0128 (2)
H5A	0.6706	0.2921	0.5172	0.015*
C6	0.42273 (17)	0.24217 (16)	0.57445 (11)	0.0110 (2)
C7	0.10655 (17)	0.19008 (16)	0.61790 (12)	0.0110 (2)
C8	0.01674 (17)	0.28193 (16)	0.73582 (11)	0.0107 (2)
C9	−0.06148 (18)	0.19737 (17)	0.83798 (12)	0.0126 (2)
H9A	−0.0505	0.0816	0.8341	0.015*
C10	−0.15600 (19)	0.28606 (17)	0.94574 (12)	0.0131 (2)
C11	−0.17726 (19)	0.45713 (17)	0.95104 (12)	0.0137 (2)
H11A	−0.2429	0.5169	1.0247	0.016*
C12	−0.10135 (18)	0.53944 (16)	0.84732 (12)	0.0117 (2)
C13	−0.00183 (18)	0.45267 (17)	0.73944 (12)	0.0120 (2)
H13A	0.0524	0.5089	0.6696	0.014*
C14	0.54604 (19)	0.27856 (19)	0.73956 (13)	0.0159 (2)
H14A	0.5188	0.2715	0.8297	0.024*
H14B	0.5450	0.3939	0.7101	0.024*
H14C	0.6725	0.1932	0.7076	0.024*
O1W	0.6637 (7)	0.9646 (10)	0.0189 (7)	0.0211 (11)	0.555 (19)
H1W1	0.7461	0.8666	−0.0151	0.032*	0.555 (19)
H2W1	0.5642	0.9957	−0.0002	0.032*	0.555 (19)
O1WX	0.6960 (8)	0.9169 (9)	0.0518 (6)	0.0125 (9)	0.445 (19)
H1WX	0.6896	0.8759	0.1225	0.019*	0.445 (19)
H2WX	0.7964	0.8353	0.0173	0.019*	0.445 (19)

	U11	U22	U33	U12	U13	U23
O1	0.0153 (4)	0.0209 (5)	0.0142 (4)	−0.0110 (4)	−0.0001 (3)	−0.0048 (4)
O2	0.0146 (4)	0.0173 (4)	0.0104 (4)	−0.0096 (4)	−0.0028 (3)	−0.0006 (3)
O3	0.0162 (4)	0.0256 (5)	0.0107 (4)	−0.0129 (4)	0.0013 (3)	0.0001 (4)
O4	0.0120 (4)	0.0231 (5)	0.0088 (4)	−0.0084 (4)	−0.0019 (3)	−0.0021 (3)
O5	0.0306 (6)	0.0212 (5)	0.0093 (4)	−0.0173 (4)	0.0021 (4)	−0.0008 (4)
O6	0.0230 (5)	0.0115 (4)	0.0118 (4)	−0.0067 (4)	−0.0022 (4)	−0.0006 (3)
C1	0.0097 (5)	0.0119 (5)	0.0097 (5)	−0.0046 (4)	−0.0009 (4)	−0.0013 (4)
C2	0.0112 (5)	0.0110 (5)	0.0102 (5)	−0.0041 (4)	−0.0029 (4)	−0.0013 (4)
C3	0.0134 (5)	0.0154 (5)	0.0096 (5)	−0.0068 (4)	−0.0012 (4)	−0.0005 (4)
C4	0.0114 (5)	0.0142 (5)	0.0110 (5)	−0.0063 (4)	−0.0007 (4)	0.0002 (4)
C5	0.0122 (5)	0.0161 (5)	0.0113 (5)	−0.0071 (4)	−0.0015 (4)	−0.0011 (4)
C6	0.0110 (5)	0.0131 (5)	0.0095 (5)	−0.0050 (4)	−0.0020 (4)	−0.0013 (4)
C7	0.0103 (5)	0.0121 (5)	0.0104 (5)	−0.0041 (4)	−0.0017 (4)	−0.0013 (4)
C8	0.0098 (5)	0.0133 (5)	0.0091 (5)	−0.0045 (4)	−0.0015 (4)	−0.0014 (4)
C9	0.0132 (5)	0.0137 (5)	0.0117 (5)	−0.0062 (4)	−0.0011 (4)	−0.0015 (4)
C10	0.0148 (5)	0.0166 (6)	0.0093 (5)	−0.0082 (5)	−0.0014 (4)	0.0002 (4)
C11	0.0159 (5)	0.0156 (6)	0.0098 (5)	−0.0066 (5)	−0.0006 (4)	−0.0019 (4)
C12	0.0122 (5)	0.0117 (5)	0.0114 (5)	−0.0038 (4)	−0.0029 (4)	−0.0017 (4)
C13	0.0124 (5)	0.0129 (5)	0.0105 (5)	−0.0053 (4)	−0.0008 (4)	−0.0008 (4)
C14	0.0139 (5)	0.0225 (6)	0.0136 (6)	−0.0070 (5)	−0.0043 (4)	−0.0046 (5)
O1W	0.0180 (11)	0.0201 (19)	0.026 (2)	−0.0063 (12)	−0.0030 (12)	−0.0079 (18)
O1WX	0.0132 (13)	0.0121 (16)	0.0115 (15)	−0.0032 (12)	−0.0041 (10)	0.0009 (12)

O1—C7	1.2437 (16)	C5—H5A	0.9500
O2—C2	1.3626 (15)	C7—C8	1.4972 (18)
O2—H1O2	0.89 (3)	C8—C13	1.3925 (18)
O3—C4	1.3546 (15)	C8—C9	1.3961 (17)
O3—H1O3	0.85 (3)	C9—C10	1.3937 (18)
O4—C6	1.3570 (15)	C9—H9A	0.9500
O4—C14	1.4344 (16)	C10—C11	1.3920 (19)
O5—C10	1.3715 (16)	C11—C12	1.3900 (18)
O5—H1O5	0.83 (3)	C11—H11A	0.9500
O6—C12	1.3724 (16)	C12—C13	1.3923 (17)
O6—H1O6	0.79 (3)	C13—H13A	0.9500
C1—C2	1.4168 (17)	C14—H14A	0.9800
C1—C6	1.4244 (17)	C14—H14B	0.9800
C1—C7	1.4628 (17)	C14—H14C	0.9800
C2—C3	1.3888 (17)	O1W—H1W1	0.8916
C3—C4	1.3942 (18)	O1W—H2W1	0.7867
C3—H3A	0.9500	O1WX—H1WX	0.8209
C4—C5	1.3998 (18)	O1WX—H2WX	0.8602
C5—C6	1.3876 (17)
C2—O2—H1O2	104.3 (18)	C13—C8—C9	121.23 (12)
C4—O3—H1O3	109.9 (16)	C13—C8—C7	120.11 (11)
C6—O4—C14	117.37 (10)	C9—C8—C7	118.45 (11)
C10—O5—H1O5	110.8 (18)	C10—C9—C8	118.71 (12)
C12—O6—H1O6	109 (2)	C10—C9—H9A	120.6
C2—C1—C6	116.96 (11)	C8—C9—H9A	120.6
C2—C1—C7	118.58 (11)	O5—C10—C11	116.99 (12)
C6—C1—C7	124.45 (11)	O5—C10—C9	122.05 (12)
O2—C2—C3	116.67 (11)	C11—C10—C9	120.96 (12)
O2—C2—C1	121.07 (11)	C12—C11—C10	119.21 (12)
C3—C2—C1	122.23 (11)	C12—C11—H11A	120.4
C2—C3—C4	118.45 (12)	C10—C11—H11A	120.4
C2—C3—H3A	120.8	O6—C12—C11	117.41 (11)
C4—C3—H3A	120.8	O6—C12—C13	121.52 (12)
O3—C4—C3	122.18 (12)	C11—C12—C13	121.06 (12)
O3—C4—C5	116.18 (11)	C12—C13—C8	118.81 (12)
C3—C4—C5	121.63 (12)	C12—C13—H13A	120.6
C6—C5—C4	119.19 (12)	C8—C13—H13A	120.6
C6—C5—H5A	120.4	O4—C14—H14A	109.5
C4—C5—H5A	120.4	O4—C14—H14B	109.5
O4—C6—C5	122.54 (11)	H14A—C14—H14B	109.5
O4—C6—C1	116.13 (11)	O4—C14—H14C	109.5
C5—C6—C1	121.26 (12)	H14A—C14—H14C	109.5
O1—C7—C1	120.63 (11)	H14B—C14—H14C	109.5
O1—C7—C8	117.04 (11)	H1W1—O1W—H2W1	112.7
C1—C7—C8	122.17 (11)	H1WX—O1WX—H2WX	97.6
C6—C1—C2—O2	175.50 (11)	C6—C1—C7—O1	−157.57 (13)
C7—C1—C2—O2	−3.32 (18)	C2—C1—C7—C8	−154.00 (12)
C6—C1—C2—C3	−6.35 (19)	C6—C1—C7—C8	27.27 (19)
C7—C1—C2—C3	174.83 (12)	O1—C7—C8—C13	−132.18 (13)
O2—C2—C3—C4	−178.32 (11)	C1—C7—C8—C13	43.14 (18)
C1—C2—C3—C4	3.46 (19)	O1—C7—C8—C9	42.51 (17)
C2—C3—C4—O3	179.32 (12)	C1—C7—C8—C9	−142.18 (13)
C2—C3—C4—C5	0.8 (2)	C13—C8—C9—C10	−1.36 (19)
O3—C4—C5—C6	179.57 (12)	C7—C8—C9—C10	−175.99 (11)
C3—C4—C5—C6	−1.8 (2)	C8—C9—C10—O5	−178.31 (12)
C14—O4—C6—C5	1.91 (18)	C8—C9—C10—C11	1.8 (2)
C14—O4—C6—C1	178.89 (11)	O5—C10—C11—C12	179.54 (12)
C4—C5—C6—O4	175.49 (12)	C9—C10—C11—C12	−0.5 (2)
C4—C5—C6—C1	−1.3 (2)	C10—C11—C12—O6	179.35 (12)
C2—C1—C6—O4	−171.78 (11)	C10—C11—C12—C13	−1.2 (2)
C7—C1—C6—O4	6.96 (19)	O6—C12—C13—C8	−178.96 (12)
C2—C1—C6—C5	5.23 (19)	C11—C12—C13—C8	1.58 (19)
C7—C1—C6—C5	−176.02 (12)	C9—C8—C13—C12	−0.30 (19)
C2—C1—C7—O1	21.15 (19)	C7—C8—C13—C12	174.24 (11)

Cg2 is the centroid of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O1	0.89 (3)	1.72 (3)	2.5453 (14)	152 (3)
O2—H1O2···O1i	0.89 (3)	2.45 (3)	2.9554 (16)	117 (3)
O3—H1O3···O5ii	0.85 (2)	1.90 (2)	2.7440 (15)	177 (3)
O5—H1O5···O1Wiii	0.83 (3)	1.76 (3)	2.574 (7)	166 (3)
O6—H1O6···O2iv	0.79 (3)	1.98 (3)	2.7220 (15)	157 (3)
O1W—H1W1···O6ii	0.89	1.91	2.746 (8)	156
C14—H14C···O1v	0.98	2.55	3.4507 (19)	152
O1WX—H2WX···Cg2vi	0.86	2.89	3.402 (7)	120

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯O1	0.89 (3)	1.72 (3)	2.5453 (14)	152 (3)
O2—H1O2⋯O1i	0.89 (3)	2.45 (3)	2.9554 (16)	117 (3)
O3—H1O3⋯O5ii	0.85 (2)	1.90 (2)	2.7440 (15)	177 (3)
O5—H1O5⋯O1Wiii	0.83 (3)	1.76 (3)	2.574 (7)	166 (3)
O6—H1O6⋯O2iv	0.79 (3)	1.98 (3)	2.7220 (15)	157 (3)
O1W—H1W1⋯O6ii	0.89	1.91	2.746 (8)	156
C14—H14C⋯O1v	0.98	2.55	3.4507 (19)	152
O1WX—H2WX⋯Cg2vi	0.86	2.89	3.402 (7)	120

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .