2-(4-Methyl­benzo­yl)benzoic acid monohydrate

In the title compound, C₁₅H₁₂O₃·H₂O, 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 mol­ecules into a three-dimensional framework.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.061
• wR factor = 0.194
• Data-to-parameter ratio = 14.2

checkCIF/PLATON results

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Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)       3000 Deg.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          3
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              H2 O

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 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
   1 ALERT type 3 Indicator that the structure quality may be low
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S1. Comment

2-(4-methylbenzoyl)benzoic acid (MBBA) is an important dye intermediate used for the synthesis of 2-methylanthraquinone (Lin et al., 2004). We report herein the crystal structure of the title compound, (I).

The asymmetric unit of the title compound, (I), (Fig. 1), contains one MBBA and one water molecules. The bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C2-C7) and B (C9-C14) are, of course, planar, and they are oriented at a dihedral angle of 69.12 (3)°.

In the crystal structure, intra- and intermolecular O-H···O hydrogen bonds (Table 1) link the molecules to form a three-dimensional framework (Fig. 2), in which they may be effective in the stabilization of the structure.

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).

S2. Experimental

The title compound was prepared according to the method described by Stanescu (1990). Crystals of (I) suitable for X-ray analysis were obtained by dissolving MBBA (2.0 g) in water (100 ml) and evaporating water slowly at room temperature for about 15 d.

S3. Refinement

H atoms were positioned geometrically, with O-H = 0.82 Å (for OH) and 0.85 Å (for H₂O) and C-H = 0.93 and 0.96 Å for aromatic and methyl H, respectively, and constrained to ride on their parent atoms with U_iso(H) = xU_eq(C,O), where x = 1.5 for OH and H₂O H and x = 1.2 for all other H atoms.

Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); 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 (Sheldrick, 2008).

Figures

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen bond is shown as dashed line.
	Fig. 2. A packing diagram of (I). Hydrogen bonds are shown as dashed lines.

2-(4-Methylbenzoyl)benzoic acid monohydrate

Crystal data

C15H12O3·H2O	Z = 2
Mr = 258.26	F(000) = 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 = 10–13°
c = 10.728 (2) Å	µ = 0.09 mm^−1
α = 79.96 (3)°	T = 294 K
β = 77.83 (3)°	Block, colorless
γ = 85.63 (3)°	0.30 × 0.20 × 0.20 mm
V = 680.6 (2) Å^3

Data collection

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

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.061	H-atom parameters constrained
wR(F^2) = 0.193	w = 1/[σ^2(Fo^2) + (0.07P)^2 + P] where P = (Fo^2 + 2Fc^2)/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

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.

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.

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

	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)

Atomic displacement parameters (Ų)

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

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
OW—HWA···O2^i	0.85	2.42	2.842 (4)	111
OW—HWB···O1^ii	0.85	2.38	2.803 (4)	111
O3—H3B···OW	0.82	1.80	2.601 (4)	165

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