4-(4-Hydroxybenzoyl)phenol mono­hydrate

The aromatic rings of the title compound, C₁₃H₁₀O₃·H₂O, are aligned at dihedral angles of 20.6 (1) and 40.8 (1)° with respect to the triangular C_ar­yl-C(=O)-C_ar­yl fragment. The hy­droxy groups are each hydrogen-bond donors to separate water mol­ecules, the water mol­ecule itself being hydrogen-bonded to one hy­droxy group and one carbonyl group. The water mol­ecule exists in an unusual four-coordinate environment in the resulting layer structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.040
• wR factor = 0.123
• Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          2

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          4
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

4,4'-Dihydroxbenzophenone exists as a O–H···O_hydroxy hydrogen-bonded chains that are linked by O–H···O_carbonyl hydrogen bonds into sheets. The first set of hydrogen bonds [2.785 (4), 2.791 (4) Å] is longer than the second set [2.624 (4), 2.627 (4) Å] (Ferguson & Glidewell, 1996). The monohydrated title compound C₁₃H₁₀O₃^.H₂O (Scheme I, Fig. 1) also adopts a hydrogen-bonded sheet motif. The aromatic rings are aligned at 20.6 (1) and 40.8 (1) ° with respect to the triangular-shaped C_aryl–C(═ O)–C_aryl fragment. The hydroxy groups are each hydrogen-bond donors to separate water molecules which also act as hydrogen-bond donors to an hydroxy group and a carbonyl group (Table 1). There are no hydroxy···carbonyl interactions, unlike those found in the anhydrous compound. The water molecule exists in an unusual four-coordinate environment in the resulting two-dimensional layer structure (Fig. 2).

Related literature

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

S2. Experimental

Anhydrous 4,4'-dihydroxybenzophenone (0.25 mmol, 0.054 g) and boric acid (0.50 mmol, 0.031 g) were dissolved in a water-ethanol mixture (50 ml/100 ml v/v). Trimethylamine (33% aqueous solution) was added until the solution registered a neutral pH. The mixture was then set aside for a few days after which yellow crystal blocks of the title compound were isolated.

S3. Refinement

Carbon-bound H-atoms were placed in calculated positions (C–H = 0.93 Å) and were included in the refinement in the riding model approximation, with U_iso(H) set to 1.2U_eq(C). The hydroxy and water H-atoms were located in a difference Fourier map, and were included in the refinement with a distance restraint of O–H = 0.84±0.01 Å and with their isotropic displacement parameters refined.

Computing details

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures

	Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C13H10O3^.H2O at the 50% probability level.
	Fig. 2. The layer structure of the title compound with hydrogen-bonding interactions shown as dashed lines.

4-(4-Hydroxybenzoyl)phenol monohydrate

Crystal data

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) Å^3	0.45 × 0.30 × 0.05 mm
Z = 4

Data collection

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

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0574P)^2 + 0.2426P] where P = (Fo^2 + 2Fc^2)/3
2572 reflections	(Δ/σ)max = 0.001
170 parameters	Δρmax = 0.22 e Å^−3
4 restraints	Δρmin = −0.17 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1w^i	0.85 (1)	1.95 (1)	2.774 (2)	164 (2)
O3—H3···O1w^ii	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···O1^iii	0.84 (1)	2.18 (2)	2.898 (2)	143 (2)

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, y−1/2, −z+1/2; (iii) x, y+1, z.