4-(4-Hydroxybenzoyl)phenol mono­hydrate

Li, H.-P.; Yang, Y.-X.; Ng, S.W.

doi:10.1107/S1600536810041425

organic compounds

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Volume 66| Part 11| November 2010| Page o2867

https://doi.org/10.1107/S1600536810041425

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4-(4-Hydroxybenzoyl)phenol monohydrate

He-Ping Li,^a Yun-Xia Yang ^a and Seik Weng Ng ^b ^*

^aKey Laboratory of Polymer Materials of Gansu Province Ministry of Education, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, Gansu, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 12 October 2010; accepted 14 October 2010; online 20 October 2010)

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.

Related literature

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

Experimental

Crystal data

C₁₃H₁₀O₃·H₂O
M_r = 232.23
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.040
wR(F²) = 0.123
S = 1.05
2572 reflections
170 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.17 e Å⁻³

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) -x, -y+1, -z+1; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x, y+1, z.

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 ).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810041425/zs2075Isup2.hkl

checkCIF report

Comment top

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 top

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

Experimental top

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.

Structure description top

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

Computing details top

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 top

	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 top

Crystal data top

C₁₃H₁₀O₃·H₂O	F(000) = 488
M_r = 232.23	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0574P)² + 0.2426P] where P = (F_o² + 2F_c²)/3
2572 reflections	(Δ/σ)_max = 0.001
170 parameters	Δρ_max = 0.22 e Å⁻³
4 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₃H₁₀O₃·H₂O	V = 1120.06 (4) Å³
M_r = 232.23	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 4.9398 (1) Å	µ = 0.10 mm⁻¹
b = 9.8273 (2) Å	T = 293 K
c = 23.1446 (4) Å	0.45 × 0.30 × 0.05 mm
β = 94.520 (1)°

Data collection top

Bruker SMART APEX diffractometer	2016 reflections with I > 2σ(I)
8356 measured reflections	R_int = 0.017
2572 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	4 restraints
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.22 e Å⁻³
2572 reflections	Δρ_min = −0.17 e Å⁻³
170 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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)

Geometric parameters (Å, º) top

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) top

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) −x, −y+1, −z+1; (ii) −x+1, y−1/2, −z+1/2; (iii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₀O₃·H₂O
M_r	232.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	4.9398 (1), 9.8273 (2), 23.1446 (4)
β (°)	94.520 (1)
V (Å³)	1120.06 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.45 × 0.30 × 0.05

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8356, 2572, 2016
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.123, 1.05
No. of reflections	2572
No. of parameters	170
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.17

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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) −x, −y+1, −z+1; (ii) −x+1, y−1/2, −z+1/2; (iii) x, y+1, z.

Acknowledgements

We thank Northeast Normal University and the University of Malaya for supporting this study.

References

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