2-(4-Methyl­benzo­yl)benzoic acid monohydrate

Song, G.-L.; Deng, S.-P.; Liu, S.; Zhu, H.-J.

doi:10.1107/S1600536808010581

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o894

doi:10.1107/S1600536808010581

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2-(4-Methylbenzoyl)benzoic acid monohydrate

Guang-Liang Song,^a Shui-Ping Deng,^a Shan Liu ^a and Hong-Jun Zhu ^a ^*

^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

(Received 31 March 2008; accepted 17 April 2008; online 23 April 2008)

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

Experimental

Crystal data

C₁₅H₁₂O₃·H₂O
M_r = 258.26
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.061
wR(F²) = 0.193
S = 1.01
2435 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.34 e Å⁻³

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) -x+1, -y, -z; (ii) x, y-1, z.

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.

Supporting information

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

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

checkCIF report

Comment top

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 top

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 top

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.

Computing details top

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 top

	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 top

Crystal data top

C₁₅H₁₂O₃·H₂O	Z = 2
M_r = 258.26	F(000) = 272
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.07P)² + P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
2435 reflections	Δρ_max = 0.39 e Å⁻³
172 parameters	Δρ_min = −0.34 e Å⁻³
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₅H₁₂O₃·H₂O	γ = 85.63 (3)°
M_r = 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)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1840 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.052
T_min = 0.973, T_max = 0.982	3 standard reflections every 120 min
2638 measured reflections	intensity decay: none
2435 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	172 parameters
wR(F²) = 0.193	H-atom parameters constrained
S = 1.01	Δρ_max = 0.39 e Å⁻³
2435 reflections	Δρ_min = −0.34 e Å⁻³

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.

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) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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)

Geometric parameters (Å, º) top

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) top

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
M_r	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)
T_min, T_max	0.973, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	2638, 2435, 1840
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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
Stanescu, M. D. (1990). Chem. Mat. Sci. 52, 67–72. CAS Google Scholar