2-(4-Methyl-benzo-yl)benzoic acid monohydrate.

In the title compound, C(15)H(12)O(3)·H(2)O, the two rings are oriented at a dihedral angle of 69.12 (3)°. In the crystal structure, intermolecular O-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional framework.

Related literature

For a general background, see: Lin et al. (2004 ▶). For a related structure, see: Stanescu (1990 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H12O3·H2O

M = 258.26

Triclinic,

a = 7.5410 (15) Å

b = 8.7480 (17) Å

c = 10.728 (2) Å

α = 79.96 (3)°

β = 77.83 (3)°

γ = 85.63 (3)°

V = 680.6 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 294 (2) K

0.30 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.973, T max = 0.982

2638 measured reflections

2435 independent reflections

1840 reflections with I > 2σ(I)

R int = 0.052

3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.193

S = 1.01

2435 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.34 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808010581/hk2446sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010581/hk2446Isup2.hkl

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

C15H12O3·H2O	Z = 2
Mr = 258.26	F000 = 272
Triclinic, P1	Dx = 1.260 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.5410 (15) Å	Cell parameters from 25 reflections
b = 8.7480 (17) Å	θ = 10–13º
c = 10.728 (2) Å	µ = 0.09 mm−1
α = 79.96 (3)º	T = 294 (2) K
β = 77.83 (3)º	Block, colorless
γ = 85.63 (3)º	0.30 × 0.20 × 0.20 mm
V = 680.6 (2) Å3

Enraf–Nonius CAD-4 diffractometer	Rint = 0.052
Radiation source: fine-focus sealed tube	θmax = 25.2º
Monochromator: graphite	θmin = 2.0º
T = 294(2) K	h = −8→9
ω/2θ scans	k = −10→10
Absorption correction: ψ scan(North et al., 1968)	l = 0→12
Tmin = 0.973, Tmax = 0.982	3 standard reflections
2638 measured reflections	every 120 min
2435 independent reflections	intensity decay: none
1840 reflections with I > 2σ(I)

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.061	H-atom parameters constrained
wR(F2) = 0.193	w = 1/[σ2(Fo2) + (0.07P)2 + P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2435 reflections	Δρmax = 0.39 e Å−3
172 parameters	Δρmin = −0.34 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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 > 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
O1	0.3154 (3)	0.5779 (3)	0.2474 (3)	0.0606 (7)
O2	0.3457 (3)	0.2365 (3)	0.1235 (2)	0.0536 (6)
O3	0.1304 (3)	0.0831 (3)	0.1112 (3)	0.0741 (9)
H3B	0.2170	0.0218	0.0961	0.111*
OW	0.3621 (4)	−0.1469 (3)	0.0679 (3)	0.0649 (7)
HWA	0.4748	−0.1368	0.0625	0.078*
HWB	0.3245	−0.2325	0.0583	0.078*
C1	0.3654 (8)	0.0097 (5)	0.7145 (4)	0.0894 (15)
H1A	0.2658	−0.0581	0.7457	0.134*
H1B	0.3792	0.0646	0.7818	0.134*
H1C	0.4749	−0.0505	0.6892	0.134*
C2	0.3286 (5)	0.1244 (4)	0.6000 (3)	0.0556 (9)
C3	0.4516 (5)	0.2367 (4)	0.5386 (3)	0.0552 (9)
H3A	0.5592	0.2396	0.5672	0.066*
C4	0.4163 (4)	0.3448 (4)	0.4351 (3)	0.0483 (8)
H4A	0.5005	0.4194	0.3948	0.058*
C5	0.2585 (4)	0.3428 (3)	0.3915 (3)	0.0426 (7)
C6	0.1346 (5)	0.2306 (4)	0.4517 (3)	0.0531 (8)
H6A	0.0271	0.2276	0.4229	0.064*
C7	0.1713 (6)	0.1227 (4)	0.5550 (3)	0.0599 (10)
H7A	0.0876	0.0475	0.5947	0.072*
C8	0.2224 (4)	0.4632 (3)	0.2816 (3)	0.0431 (7)
C9	0.0626 (4)	0.4530 (3)	0.2224 (3)	0.0412 (7)
C10	−0.0716 (4)	0.5713 (4)	0.2360 (3)	0.0491 (8)
H10A	−0.0566	0.6524	0.2780	0.059*
C11	−0.2265 (4)	0.5683 (4)	0.1873 (3)	0.0537 (9)
H11A	−0.3156	0.6474	0.1970	0.064*
C12	−0.2500 (4)	0.4501 (4)	0.1250 (3)	0.0539 (9)
H12A	−0.3550	0.4489	0.0928	0.065*
C13	−0.1169 (4)	0.3311 (4)	0.1096 (3)	0.0471 (8)
H13A	−0.1338	0.2506	0.0675	0.056*
C14	0.0391 (4)	0.3326 (3)	0.1566 (3)	0.0410 (7)
C15	0.1881 (4)	0.2129 (3)	0.1288 (3)	0.0438 (7)

	U11	U22	U33	U12	U13	U23
O1	0.0532 (14)	0.0482 (14)	0.0769 (17)	−0.0065 (11)	−0.0189 (12)	0.0089 (12)
O2	0.0396 (13)	0.0515 (14)	0.0682 (15)	0.0127 (10)	−0.0078 (11)	−0.0156 (11)
O3	0.0535 (15)	0.0465 (14)	0.124 (2)	0.0084 (11)	−0.0124 (15)	−0.0292 (15)
OW	0.0646 (16)	0.0387 (13)	0.0809 (18)	0.0083 (11)	0.0040 (13)	−0.0081 (12)
C1	0.128 (4)	0.062 (3)	0.071 (3)	0.016 (3)	−0.027 (3)	0.009 (2)
C2	0.077 (3)	0.0425 (18)	0.0462 (19)	0.0114 (17)	−0.0147 (17)	−0.0077 (15)
C3	0.059 (2)	0.062 (2)	0.0473 (19)	0.0106 (17)	−0.0213 (16)	−0.0103 (16)
C4	0.0482 (19)	0.0444 (18)	0.0505 (18)	0.0008 (14)	−0.0093 (15)	−0.0050 (14)
C5	0.0420 (17)	0.0380 (16)	0.0456 (17)	0.0032 (13)	−0.0067 (13)	−0.0059 (13)
C6	0.058 (2)	0.0505 (19)	0.0506 (19)	−0.0074 (16)	−0.0137 (16)	−0.0015 (15)
C7	0.082 (3)	0.0445 (19)	0.051 (2)	−0.0144 (18)	−0.0119 (18)	0.0037 (15)
C8	0.0378 (16)	0.0369 (16)	0.0499 (18)	0.0034 (13)	−0.0020 (13)	−0.0049 (13)
C9	0.0350 (16)	0.0399 (16)	0.0415 (16)	0.0079 (12)	−0.0010 (12)	0.0007 (13)
C10	0.0444 (18)	0.0440 (18)	0.0552 (19)	0.0105 (14)	−0.0036 (15)	−0.0114 (15)
C11	0.0408 (18)	0.056 (2)	0.058 (2)	0.0182 (15)	−0.0038 (15)	−0.0090 (16)
C12	0.0344 (17)	0.065 (2)	0.057 (2)	0.0076 (15)	−0.0078 (15)	−0.0010 (17)
C13	0.0420 (18)	0.0439 (17)	0.0506 (18)	−0.0004 (14)	−0.0039 (14)	−0.0022 (14)
C14	0.0338 (16)	0.0361 (16)	0.0465 (17)	0.0058 (12)	−0.0004 (13)	−0.0012 (13)
C15	0.0453 (19)	0.0362 (16)	0.0479 (18)	0.0055 (13)	−0.0072 (14)	−0.0068 (13)

O1—C8	1.227 (4)	C5—C8	1.494 (4)
O2—C15	1.209 (4)	C6—C7	1.386 (5)
O3—C15	1.303 (4)	C6—H6A	0.9300
O3—H3B	0.8200	C7—H7A	0.9300
OW—HWA	0.8501	C8—C9	1.491 (4)
OW—HWB	0.8500	C9—C10	1.396 (4)
C1—C2	1.505 (5)	C9—C14	1.407 (4)
C1—H1A	0.9600	C10—C11	1.380 (5)
C1—H1B	0.9600	C10—H10A	0.9300
C1—H1C	0.9600	C11—C12	1.366 (5)
C2—C7	1.374 (5)	C11—H11A	0.9300
C2—C3	1.384 (5)	C12—C13	1.396 (5)
C3—C4	1.386 (5)	C12—H12A	0.9300
C3—H3A	0.9300	C13—C14	1.376 (4)
C4—C5	1.370 (4)	C13—H13A	0.9300
C4—H4A	0.9300	C14—C15	1.495 (4)
C5—C6	1.385 (4)
C15—O3—H3B	109.5	C6—C7—H7A	119.3
HWA—OW—HWB	120.0	O1—C8—C9	119.6 (3)
C2—C1—H1A	109.5	O1—C8—C5	119.7 (3)
C2—C1—H1B	109.5	C9—C8—C5	120.4 (3)
H1A—C1—H1B	109.5	C10—C9—C14	119.1 (3)
C2—C1—H1C	109.5	C10—C9—C8	116.5 (3)
H1A—C1—H1C	109.5	C14—C9—C8	124.4 (3)
H1B—C1—H1C	109.5	C11—C10—C9	120.2 (3)
C7—C2—C3	118.2 (3)	C11—C10—H10A	119.9
C7—C2—C1	121.2 (4)	C9—C10—H10A	119.9
C3—C2—C1	120.6 (4)	C12—C11—C10	120.5 (3)
C2—C3—C4	120.8 (3)	C12—C11—H11A	119.8
C2—C3—H3A	119.6	C10—C11—H11A	119.8
C4—C3—H3A	119.6	C11—C12—C13	120.2 (3)
C5—C4—C3	120.6 (3)	C11—C12—H12A	119.9
C5—C4—H4A	119.7	C13—C12—H12A	119.9
C3—C4—H4A	119.7	C14—C13—C12	120.2 (3)
C4—C5—C6	119.2 (3)	C14—C13—H13A	119.9
C4—C5—C8	119.3 (3)	C12—C13—H13A	119.9
C6—C5—C8	121.5 (3)	C13—C14—C9	119.7 (3)
C5—C6—C7	119.8 (3)	C13—C14—C15	119.7 (3)
C5—C6—H6A	120.1	C9—C14—C15	120.4 (3)
C7—C6—H6A	120.1	O2—C15—O3	124.3 (3)
C2—C7—C6	121.5 (3)	O2—C15—C14	122.5 (3)
C2—C7—H7A	119.3	O3—C15—C14	113.3 (3)
C7—C2—C3—C4	0.3 (5)	C5—C8—C9—C14	−64.3 (4)
C1—C2—C3—C4	−178.5 (3)	C14—C9—C10—C11	1.1 (5)
C2—C3—C4—C5	0.1 (5)	C8—C9—C10—C11	−178.1 (3)
C3—C4—C5—C6	−0.4 (5)	C9—C10—C11—C12	−0.2 (5)
C3—C4—C5—C8	178.6 (3)	C10—C11—C12—C13	−0.2 (5)
C4—C5—C6—C7	0.3 (5)	C11—C12—C13—C14	−0.3 (5)
C8—C5—C6—C7	−178.7 (3)	C12—C13—C14—C9	1.2 (4)
C3—C2—C7—C6	−0.5 (5)	C12—C13—C14—C15	−174.3 (3)
C1—C2—C7—C6	178.3 (4)	C10—C9—C14—C13	−1.6 (4)
C5—C6—C7—C2	0.2 (5)	C8—C9—C14—C13	177.6 (3)
C4—C5—C8—O1	−13.4 (4)	C10—C9—C14—C15	173.9 (3)
C6—C5—C8—O1	165.5 (3)	C8—C9—C14—C15	−7.0 (4)
C4—C5—C8—C9	172.9 (3)	C13—C14—C15—O2	152.2 (3)
C6—C5—C8—C9	−8.1 (4)	C9—C14—C15—O2	−23.2 (5)
O1—C8—C9—C10	−58.8 (4)	C13—C14—C15—O3	−27.6 (4)
C5—C8—C9—C10	114.9 (3)	C9—C14—C15—O3	156.9 (3)
O1—C8—C9—C14	122.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
OW—HWA···O2i	0.85	2.42	2.842 (4)	111
OW—HWB···O1ii	0.85	2.38	2.803 (4)	111
O3—H3B···OW	0.82	1.80	2.601 (4)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
OW—HWA⋯O2i	0.85	2.42	2.842 (4)	111
OW—HWB⋯O1ii	0.85	2.38	2.803 (4)	111
O3—H3B⋯OW	0.82	1.80	2.601 (4)	165

Symmetry codes: (i) ; (ii) .