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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): o894.
Published online 2008 April 23. doi:  10.1107/S1600536808010581
PMCID: PMC2961241

2-(4-Methyl­benzo­yl)benzoic acid monohydrate

Abstract

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.

Related literature

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

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Object name is e-64-0o894-scheme1.jpg

Experimental

Crystal data

  • C15H12O3·H2O
  • M r = 258.26
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o894-efi1.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

supplementary crystallographic information

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.

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.

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 Uiso(H) = xUeq(C,O), where x = 1.5 for OH and H2O H and x = 1.2 for all other H atoms.

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.

Crystal data

C15H12O3·H2OZ = 2
Mr = 258.26F000 = 272
Triclinic, P1Dx = 1.260 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 7.5410 (15) ÅCell parameters from 25 reflections
b = 8.7480 (17) Åθ = 10–13º
c = 10.728 (2) ŵ = 0.09 mm1
α = 79.96 (3)ºT = 294 (2) K
β = 77.83 (3)ºBlock, colorless
γ = 85.63 (3)º0.30 × 0.20 × 0.20 mm
V = 680.6 (2) Å3

Data collection

Enraf–Nonius CAD-4 diffractometerRint = 0.052
Radiation source: fine-focus sealed tubeθmax = 25.2º
Monochromator: graphiteθmin = 2.0º
T = 294(2) Kh = −8→9
ω/2θ scansk = −10→10
Absorption correction: ψ scan(North et al., 1968)l = 0→12
Tmin = 0.973, Tmax = 0.9823 standard reflections
2638 measured reflections every 120 min
2435 independent reflections intensity decay: none
1840 reflections with I > 2σ(I)

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.061H-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 reflectionsΔρmax = 0.39 e Å3
172 parametersΔρmin = −0.34 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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 (Å2)

xyzUiso*/Ueq
O10.3154 (3)0.5779 (3)0.2474 (3)0.0606 (7)
O20.3457 (3)0.2365 (3)0.1235 (2)0.0536 (6)
O30.1304 (3)0.0831 (3)0.1112 (3)0.0741 (9)
H3B0.21700.02180.09610.111*
OW0.3621 (4)−0.1469 (3)0.0679 (3)0.0649 (7)
HWA0.4748−0.13680.06250.078*
HWB0.3245−0.23250.05830.078*
C10.3654 (8)0.0097 (5)0.7145 (4)0.0894 (15)
H1A0.2658−0.05810.74570.134*
H1B0.37920.06460.78180.134*
H1C0.4749−0.05050.68920.134*
C20.3286 (5)0.1244 (4)0.6000 (3)0.0556 (9)
C30.4516 (5)0.2367 (4)0.5386 (3)0.0552 (9)
H3A0.55920.23960.56720.066*
C40.4163 (4)0.3448 (4)0.4351 (3)0.0483 (8)
H4A0.50050.41940.39480.058*
C50.2585 (4)0.3428 (3)0.3915 (3)0.0426 (7)
C60.1346 (5)0.2306 (4)0.4517 (3)0.0531 (8)
H6A0.02710.22760.42290.064*
C70.1713 (6)0.1227 (4)0.5550 (3)0.0599 (10)
H7A0.08760.04750.59470.072*
C80.2224 (4)0.4632 (3)0.2816 (3)0.0431 (7)
C90.0626 (4)0.4530 (3)0.2224 (3)0.0412 (7)
C10−0.0716 (4)0.5713 (4)0.2360 (3)0.0491 (8)
H10A−0.05660.65240.27800.059*
C11−0.2265 (4)0.5683 (4)0.1873 (3)0.0537 (9)
H11A−0.31560.64740.19700.064*
C12−0.2500 (4)0.4501 (4)0.1250 (3)0.0539 (9)
H12A−0.35500.44890.09280.065*
C13−0.1169 (4)0.3311 (4)0.1096 (3)0.0471 (8)
H13A−0.13380.25060.06750.056*
C140.0391 (4)0.3326 (3)0.1566 (3)0.0410 (7)
C150.1881 (4)0.2129 (3)0.1288 (3)0.0438 (7)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0532 (14)0.0482 (14)0.0769 (17)−0.0065 (11)−0.0189 (12)0.0089 (12)
O20.0396 (13)0.0515 (14)0.0682 (15)0.0127 (10)−0.0078 (11)−0.0156 (11)
O30.0535 (15)0.0465 (14)0.124 (2)0.0084 (11)−0.0124 (15)−0.0292 (15)
OW0.0646 (16)0.0387 (13)0.0809 (18)0.0083 (11)0.0040 (13)−0.0081 (12)
C10.128 (4)0.062 (3)0.071 (3)0.016 (3)−0.027 (3)0.009 (2)
C20.077 (3)0.0425 (18)0.0462 (19)0.0114 (17)−0.0147 (17)−0.0077 (15)
C30.059 (2)0.062 (2)0.0473 (19)0.0106 (17)−0.0213 (16)−0.0103 (16)
C40.0482 (19)0.0444 (18)0.0505 (18)0.0008 (14)−0.0093 (15)−0.0050 (14)
C50.0420 (17)0.0380 (16)0.0456 (17)0.0032 (13)−0.0067 (13)−0.0059 (13)
C60.058 (2)0.0505 (19)0.0506 (19)−0.0074 (16)−0.0137 (16)−0.0015 (15)
C70.082 (3)0.0445 (19)0.051 (2)−0.0144 (18)−0.0119 (18)0.0037 (15)
C80.0378 (16)0.0369 (16)0.0499 (18)0.0034 (13)−0.0020 (13)−0.0049 (13)
C90.0350 (16)0.0399 (16)0.0415 (16)0.0079 (12)−0.0010 (12)0.0007 (13)
C100.0444 (18)0.0440 (18)0.0552 (19)0.0105 (14)−0.0036 (15)−0.0114 (15)
C110.0408 (18)0.056 (2)0.058 (2)0.0182 (15)−0.0038 (15)−0.0090 (16)
C120.0344 (17)0.065 (2)0.057 (2)0.0076 (15)−0.0078 (15)−0.0010 (17)
C130.0420 (18)0.0439 (17)0.0506 (18)−0.0004 (14)−0.0039 (14)−0.0022 (14)
C140.0338 (16)0.0361 (16)0.0465 (17)0.0058 (12)−0.0004 (13)−0.0012 (13)
C150.0453 (19)0.0362 (16)0.0479 (18)0.0055 (13)−0.0072 (14)−0.0068 (13)

Geometric parameters (Å, °)

O1—C81.227 (4)C5—C81.494 (4)
O2—C151.209 (4)C6—C71.386 (5)
O3—C151.303 (4)C6—H6A0.9300
O3—H3B0.8200C7—H7A0.9300
OW—HWA0.8501C8—C91.491 (4)
OW—HWB0.8500C9—C101.396 (4)
C1—C21.505 (5)C9—C141.407 (4)
C1—H1A0.9600C10—C111.380 (5)
C1—H1B0.9600C10—H10A0.9300
C1—H1C0.9600C11—C121.366 (5)
C2—C71.374 (5)C11—H11A0.9300
C2—C31.384 (5)C12—C131.396 (5)
C3—C41.386 (5)C12—H12A0.9300
C3—H3A0.9300C13—C141.376 (4)
C4—C51.370 (4)C13—H13A0.9300
C4—H4A0.9300C14—C151.495 (4)
C5—C61.385 (4)
C15—O3—H3B109.5C6—C7—H7A119.3
HWA—OW—HWB120.0O1—C8—C9119.6 (3)
C2—C1—H1A109.5O1—C8—C5119.7 (3)
C2—C1—H1B109.5C9—C8—C5120.4 (3)
H1A—C1—H1B109.5C10—C9—C14119.1 (3)
C2—C1—H1C109.5C10—C9—C8116.5 (3)
H1A—C1—H1C109.5C14—C9—C8124.4 (3)
H1B—C1—H1C109.5C11—C10—C9120.2 (3)
C7—C2—C3118.2 (3)C11—C10—H10A119.9
C7—C2—C1121.2 (4)C9—C10—H10A119.9
C3—C2—C1120.6 (4)C12—C11—C10120.5 (3)
C2—C3—C4120.8 (3)C12—C11—H11A119.8
C2—C3—H3A119.6C10—C11—H11A119.8
C4—C3—H3A119.6C11—C12—C13120.2 (3)
C5—C4—C3120.6 (3)C11—C12—H12A119.9
C5—C4—H4A119.7C13—C12—H12A119.9
C3—C4—H4A119.7C14—C13—C12120.2 (3)
C4—C5—C6119.2 (3)C14—C13—H13A119.9
C4—C5—C8119.3 (3)C12—C13—H13A119.9
C6—C5—C8121.5 (3)C13—C14—C9119.7 (3)
C5—C6—C7119.8 (3)C13—C14—C15119.7 (3)
C5—C6—H6A120.1C9—C14—C15120.4 (3)
C7—C6—H6A120.1O2—C15—O3124.3 (3)
C2—C7—C6121.5 (3)O2—C15—C14122.5 (3)
C2—C7—H7A119.3O3—C15—C14113.3 (3)
C7—C2—C3—C40.3 (5)C5—C8—C9—C14−64.3 (4)
C1—C2—C3—C4−178.5 (3)C14—C9—C10—C111.1 (5)
C2—C3—C4—C50.1 (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—C8178.6 (3)C10—C11—C12—C13−0.2 (5)
C4—C5—C6—C70.3 (5)C11—C12—C13—C14−0.3 (5)
C8—C5—C6—C7−178.7 (3)C12—C13—C14—C91.2 (4)
C3—C2—C7—C6−0.5 (5)C12—C13—C14—C15−174.3 (3)
C1—C2—C7—C6178.3 (4)C10—C9—C14—C13−1.6 (4)
C5—C6—C7—C20.2 (5)C8—C9—C14—C13177.6 (3)
C4—C5—C8—O1−13.4 (4)C10—C9—C14—C15173.9 (3)
C6—C5—C8—O1165.5 (3)C8—C9—C14—C15−7.0 (4)
C4—C5—C8—C9172.9 (3)C13—C14—C15—O2152.2 (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—C10114.9 (3)C9—C14—C15—O3156.9 (3)
O1—C8—C9—C14122.1 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
OW—HWA···O2i0.852.422.842 (4)111
OW—HWB···O1ii0.852.382.803 (4)111
O3—H3B···OW0.821.802.601 (4)165

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2446).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Enraf–Nonius (1985). CAD-4 Software Enraf–Nonius, Delft, The Netherlands.
  • Harms, K. & Wocadlo, S. (1995). XCAD4 University of Marburg, Germany.
  • Lin, L., Yang, J. Z. & Xu, L. (2004). Ranliao Yu Ranse, 41, 289–290.
  • North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Stanescu, M. D. (1990). Chem. Mat. Sci.52, 67–72.

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