4-(4-Hydroxybenzoyl)phenol mono-hydrate.

The aromatic rings of the title compound, C(13)H(10)O(3)·H(2)O, are aligned at dihedral angles of 20.6 (1) and 40.8 (1)° with respect to the triangular C(ar-yl)-C(=O)-C(ar-yl) fragment. The hy-droxy groups are each hydrogen-bond donors to separate water mol-ecules, the water mol-ecule itself being hydrogen-bonded to one hy-droxy group and one carbonyl group. The water mol-ecule exists in an unusual four-coordinate environment in the resulting layer structure.

Related literature

For the crystal structure of anhydrous 4,4′-dihy­droxy­benzophenone, see: Ferguson & Glidewell (1996 ▶).

Experimental

Crystal data

C13H10O3·H2O

M = 232.23

Monoclinic,

a = 4.9398 (1) Å

b = 9.8273 (2) Å

c = 23.1446 (4) Å

β = 94.520 (1)°

V = 1120.06 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.45 × 0.30 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer

8356 measured reflections

2572 independent reflections

2016 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.123

S = 1.05

2572 reflections

170 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810041425/zs2075sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041425/zs2075Isup2.hkl

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

C13H10O3·H2O	F(000) = 488
Mr = 232.23	Dx = 1.377 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3494 reflections
a = 4.9398 (1) Å	θ = 2.7–27.2°
b = 9.8273 (2) Å	µ = 0.10 mm−1
c = 23.1446 (4) Å	T = 293 K
β = 94.520 (1)°	Block, yellow
V = 1120.06 (4) Å3	0.45 × 0.30 × 0.05 mm
Z = 4

Bruker SMART APEX diffractometer	2016 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.017
graphite	θmax = 27.5°, θmin = 1.8°
ω scans	h = −6→6
8356 measured reflections	k = −11→12
2572 independent reflections	l = −29→29

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0574P)2 + 0.2426P] where P = (Fo2 + 2Fc2)/3
2572 reflections	(Δ/σ)max = 0.001
170 parameters	Δρmax = 0.22 e Å−3
4 restraints	Δρmin = −0.17 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.

	x	y	z	Uiso*/Ueq
O1	0.2714 (2)	0.12226 (11)	0.49586 (5)	0.0570 (3)
O2	0.5003 (3)	0.68859 (12)	0.38317 (5)	0.0671 (4)
O3	1.0143 (3)	0.54977 (14)	0.15066 (5)	0.0634 (3)
O1W	0.1638 (3)	0.86726 (12)	0.43550 (5)	0.0554 (3)
C1	0.5324 (3)	0.57501 (15)	0.36223 (6)	0.0465 (3)
C2	0.4542 (3)	0.45204 (15)	0.39381 (6)	0.0442 (3)
C3	0.2632 (4)	0.46347 (17)	0.43426 (8)	0.0676 (5)
H3A	0.1772	0.5466	0.4387	0.081*
C4	0.1979 (4)	0.35531 (17)	0.46788 (8)	0.0668 (5)
H4	0.0674	0.3653	0.4944	0.080*
C5	0.3249 (3)	0.23209 (15)	0.46244 (6)	0.0454 (3)
C6	0.5141 (3)	0.21717 (16)	0.42219 (7)	0.0536 (4)
H6	0.5993	0.1338	0.4180	0.064*
C7	0.5768 (3)	0.32592 (16)	0.38821 (6)	0.0508 (4)
H7	0.7037	0.3148	0.3610	0.061*
C8	0.6547 (3)	0.56332 (14)	0.30623 (6)	0.0426 (3)
C9	0.8488 (3)	0.65824 (16)	0.29241 (7)	0.0509 (4)
H9	0.8994	0.7271	0.3186	0.061*
C10	0.9667 (3)	0.65163 (17)	0.24064 (7)	0.0552 (4)
H10	1.1004	0.7139	0.2326	0.066*
C11	0.8866 (3)	0.55235 (15)	0.20044 (6)	0.0459 (3)
C12	0.6853 (3)	0.46052 (15)	0.21229 (6)	0.0457 (3)
H12A	0.6253	0.3962	0.1847	0.055*
C13	0.5745 (3)	0.46505 (14)	0.26519 (6)	0.0451 (3)
H13	0.4440	0.4013	0.2735	0.054*
H1	0.147 (4)	0.141 (2)	0.5179 (8)	0.091 (7)*
H3	0.946 (5)	0.4859 (19)	0.1296 (9)	0.103 (9)*
H11	0.260 (4)	0.8047 (19)	0.4233 (10)	0.101 (8)*
H12	0.262 (5)	0.921 (2)	0.4565 (10)	0.111 (9)*

	U11	U22	U33	U12	U13	U23
O1	0.0723 (7)	0.0453 (6)	0.0572 (7)	−0.0005 (5)	0.0286 (6)	0.0009 (5)
O2	0.1019 (10)	0.0421 (6)	0.0609 (7)	0.0052 (6)	0.0298 (7)	−0.0063 (5)
O3	0.0714 (8)	0.0729 (8)	0.0487 (6)	−0.0131 (6)	0.0223 (6)	−0.0028 (6)
O1W	0.0679 (7)	0.0496 (7)	0.0508 (6)	−0.0027 (6)	0.0174 (6)	−0.0040 (5)
C1	0.0537 (8)	0.0424 (8)	0.0440 (7)	0.0039 (6)	0.0080 (6)	−0.0038 (6)
C2	0.0493 (8)	0.0432 (8)	0.0413 (7)	0.0013 (6)	0.0103 (6)	−0.0042 (6)
C3	0.0859 (12)	0.0445 (9)	0.0784 (12)	0.0133 (8)	0.0452 (10)	−0.0004 (8)
C4	0.0808 (12)	0.0522 (9)	0.0741 (11)	0.0072 (8)	0.0478 (10)	−0.0008 (8)
C5	0.0519 (8)	0.0429 (8)	0.0429 (7)	−0.0032 (6)	0.0118 (6)	−0.0021 (6)
C6	0.0650 (9)	0.0450 (8)	0.0539 (9)	0.0108 (7)	0.0234 (7)	0.0010 (7)
C7	0.0582 (9)	0.0501 (8)	0.0470 (8)	0.0083 (7)	0.0223 (7)	0.0007 (6)
C8	0.0485 (7)	0.0388 (7)	0.0411 (7)	0.0031 (6)	0.0074 (6)	0.0012 (6)
C9	0.0605 (9)	0.0439 (8)	0.0486 (8)	−0.0085 (7)	0.0064 (7)	−0.0056 (6)
C10	0.0595 (9)	0.0514 (9)	0.0559 (9)	−0.0154 (7)	0.0123 (7)	−0.0002 (7)
C11	0.0505 (8)	0.0468 (8)	0.0413 (7)	0.0020 (6)	0.0089 (6)	0.0052 (6)
C12	0.0539 (8)	0.0426 (8)	0.0408 (7)	−0.0022 (6)	0.0045 (6)	−0.0030 (6)
C13	0.0497 (8)	0.0407 (7)	0.0458 (7)	−0.0041 (6)	0.0088 (6)	−0.0001 (6)

O1—C5	1.3659 (17)	C5—C6	1.3784 (19)
O1—H1	0.847 (10)	C6—C7	1.377 (2)
O2—C1	1.2322 (18)	C6—H6	0.9300
O3—C11	1.3566 (17)	C7—H7	0.9300
O3—H3	0.847 (10)	C8—C13	1.390 (2)
O1W—H11	0.841 (10)	C8—C9	1.393 (2)
O1W—H12	0.844 (10)	C9—C10	1.375 (2)
C1—C8	1.4771 (19)	C9—H9	0.9300
C1—C2	1.479 (2)	C10—C11	1.384 (2)
C2—C3	1.385 (2)	C10—H10	0.9300
C2—C7	1.390 (2)	C11—C12	1.386 (2)
C3—C4	1.371 (2)	C12—C13	1.3810 (19)
C3—H3A	0.9300	C12—H12A	0.9300
C4—C5	1.374 (2)	C13—H13	0.9300
C4—H4	0.9300
C5—O1—H1	110.4 (16)	C6—C7—C2	121.32 (13)
C11—O3—H3	108.2 (17)	C6—C7—H7	119.3
H11—O1W—H12	110 (2)	C2—C7—H7	119.3
O2—C1—C8	119.34 (13)	C13—C8—C9	118.22 (13)
O2—C1—C2	119.92 (13)	C13—C8—C1	122.62 (13)
C8—C1—C2	120.73 (12)	C9—C8—C1	119.08 (13)
C3—C2—C7	117.41 (14)	C10—C9—C8	121.01 (14)
C3—C2—C1	119.09 (13)	C10—C9—H9	119.5
C7—C2—C1	123.34 (12)	C8—C9—H9	119.5
C4—C3—C2	121.61 (15)	C9—C10—C11	120.05 (14)
C4—C3—H3A	119.2	C9—C10—H10	120.0
C2—C3—H3A	119.2	C11—C10—H10	120.0
C3—C4—C5	120.11 (14)	O3—C11—C10	117.16 (13)
C3—C4—H4	119.9	O3—C11—C12	122.99 (14)
C5—C4—H4	119.9	C10—C11—C12	119.84 (13)
O1—C5—C4	122.29 (12)	C13—C12—C11	119.68 (13)
O1—C5—C6	118.08 (13)	C13—C12—H12A	120.2
C4—C5—C6	119.64 (14)	C11—C12—H12A	120.2
C7—C6—C5	119.90 (14)	C12—C13—C8	121.10 (13)
C7—C6—H6	120.1	C12—C13—H13	119.5
C5—C6—H6	120.1	C8—C13—H13	119.5
O2—C1—C2—C3	22.9 (2)	O2—C1—C8—C13	−144.18 (16)
C8—C1—C2—C3	−158.45 (16)	C2—C1—C8—C13	37.2 (2)
O2—C1—C2—C7	−152.26 (16)	O2—C1—C8—C9	32.5 (2)
C8—C1—C2—C7	26.4 (2)	C2—C1—C8—C9	−146.10 (15)
C7—C2—C3—C4	0.4 (3)	C13—C8—C9—C10	−2.8 (2)
C1—C2—C3—C4	−175.06 (18)	C1—C8—C9—C10	−179.63 (15)
C2—C3—C4—C5	0.8 (3)	C8—C9—C10—C11	2.2 (3)
C3—C4—C5—O1	178.47 (18)	C9—C10—C11—O3	−178.83 (15)
C3—C4—C5—C6	−1.3 (3)	C9—C10—C11—C12	0.6 (2)
O1—C5—C6—C7	−179.09 (15)	O3—C11—C12—C13	176.64 (14)
C4—C5—C6—C7	0.7 (3)	C10—C11—C12—C13	−2.8 (2)
C5—C6—C7—C2	0.5 (3)	C11—C12—C13—C8	2.2 (2)
C3—C2—C7—C6	−1.0 (3)	C9—C8—C13—C12	0.6 (2)
C1—C2—C7—C6	174.23 (15)	C1—C8—C13—C12	177.31 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1wi	0.85 (1)	1.95 (1)	2.774 (2)	164 (2)
O3—H3···O1wii	0.85 (1)	1.95 (1)	2.773 (2)	164 (2)
O1w—H11···O2	0.84 (1)	1.93 (1)	2.762 (2)	168 (2)
O1w—H12···O1iii	0.84 (1)	2.18 (2)	2.898 (2)	143 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O1wi	0.85 (1)	1.95 (1)	2.774 (2)	164 (2)
O3—H3⋯O1wii	0.85 (1)	1.95 (1)	2.773 (2)	164 (2)
O1w—H11⋯O2	0.84 (1)	1.93 (1)	2.762 (2)	168 (2)
O1w—H12⋯O1iii	0.84 (1)	2.18 (2)	2.898 (2)	143 (2)

Symmetry codes: (i) ; (ii) ; (iii) .