organic compounds
2-(4-Methylbenzoyl)benzoic acid monohydrate
aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
*Correspondence e-mail: zhuhj@njut.edu.cn
In the title compound, C15H12O3·H2O, the two rings are oriented at a dihedral angle of 69.12 (3)°. In the 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). For a related structure, see: Stanescu (1990). For bond-length data, see: Allen et al. (1987).
Experimental
Crystal data
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Refinement
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Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell 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.
Supporting information
10.1107/S1600536808010581/hk2446sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808010581/hk2446Isup2.hkl
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.
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.
Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell
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).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) Å3 |
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 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 |
C15H12O3·H2O | γ = 85.63 (3)° |
Mr = 258.26 | V = 680.6 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.5410 (15) Å | Mo Kα radiation |
b = 8.7480 (17) Å | µ = 0.09 mm−1 |
c = 10.728 (2) Å | T = 294 K |
α = 79.96 (3)° | 0.30 × 0.20 × 0.20 mm |
β = 77.83 (3)° |
Enraf–Nonius CAD-4 diffractometer | 1840 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.052 |
Tmin = 0.973, Tmax = 0.982 | 3 standard reflections every 120 min |
2638 measured reflections | intensity decay: none |
2435 independent reflections |
R[F2 > 2σ(F2)] = 0.061 | 172 parameters |
wR(F2) = 0.193 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.39 e Å−3 |
2435 reflections | Δρmin = −0.34 e Å−3 |
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 |
Symmetry codes: (i) −x+1, −y, −z; (ii) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C15H12O3·H2O |
Mr | 258.26 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 294 |
a, b, c (Å) | 7.5410 (15), 8.7480 (17), 10.728 (2) |
α, β, γ (°) | 79.96 (3), 77.83 (3), 85.63 (3) |
V (Å3) | 680.6 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.973, 0.982 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2638, 2435, 1840 |
Rint | 0.052 |
(sin θ/λ)max (Å−1) | 0.598 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.061, 0.193, 1.01 |
No. of reflections | 2435 |
No. of parameters | 172 |
No. of restraints | ? |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.39, −0.34 |
Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
OW—HWA···O2i | 0.85 | 2.42 | 2.842 (4) | 111.00 |
OW—HWB···O1ii | 0.85 | 2.38 | 2.803 (4) | 111.00 |
O3—H3B···OW | 0.82 | 1.80 | 2.601 (4) | 165.00 |
Symmetry codes: (i) −x+1, −y, −z; (ii) x, y−1, z. |
Acknowledgements
The authors thank the Center of Testing and Analysis, Nanjing University, for support.
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. CrossRef Web of Science Google Scholar
Enraf–Nonius (1985). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Lin, L., Yang, J. Z. & Xu, L. (2004). Ranliao Yu Ranse, 41, 289–290. CAS Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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.