2-(4-Dimethyl­amino-2-hydroxy­benzoyl)benzoic acid methanol solvate

Jin-Chun Guo; Qing-Hao Liu; Jin-Ying Guo; Mei-Zhu Chen; Rui-Wang Zhang

doi:10.1107/S1600536808038403

. 2008 Nov 22;64(Pt 12):o2419. doi: 10.1107/S1600536808038403

2-(4-Dimethylamino-2-hydroxybenzoyl)benzoic acid methanol solvate

Jin-Chun Guo ^a, Qing-Hao Liu ^b,^*, Jin-Ying Guo ^c, Mei-Zhu Chen ^b, Rui-Wang Zhang ^b

PMCID: PMC2959920 PMID: 21581387

Abstract

In the title compound, C₁₆H₁₅NO₄·CH₄O, the dihedral angle between the benzene rings is 75.21 (5)°. The structure is stabilized by an intramolecular O—H⋯O interaction [O⋯O = 2.589 (2) Å]. The solvent molecule links symmetry-related molecules of the complex via hydrogen bonds with O⋯O separations of 2.631 (2) and 2.815 (2) Å. C—H⋯O hydrogen bonds are also present.

Related literature

For a related structure, see: Yan et al. (2006 ▶). For synthetic applications, see: Hellmut & Lamm (1977 ▶); Minru et al. (1977 ▶); Yojiro et al. (1992 ▶); Lee et al. (1998 ▶); Luo et al. (1994 ▶).

Experimental

Crystal data

C₁₆H₁₅NO₄·CH₄O
M _r = 317.33
Triclinic,
a = 7.1438 (14) Å
b = 7.3021 (15) Å
c = 16.613 (3) Å
α = 83.92 (3)°
β = 80.21 (3)°
γ = 64.94 (3)°
V = 773.0 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 113 (2) K
0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.980, T _max = 0.988
12548 measured reflections
3528 independent reflections
2679 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.109
S = 1.06
3528 reflections
220 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2005 ▶); 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.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038403/pv2121sup1.cif

e-64-o2419-sup1.cif^{(19.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038403/pv2121Isup2.hkl

e-64-o2419-Isup2.hkl^{(173KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.92 (2)	1.75 (2)	2.589 (2)	151 (1)
O4—H4⋯O5ⁱ	0.94 (2)	1.70 (2)	2.631 (2)	168 (2)
O5—H5⋯O2	0.87 (2)	1.95 (2)	2.815 (2)	178 (2)
C7—H7B⋯O3ⁱⁱ	0.98	2.54	3.463 (2)	156
C13—H13⋯O5ⁱⁱⁱ	0.95	2.53	3.331 (2)	142

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

supplementary crystallographic information

Comment

The title compound, (I), is an intermediate in the synthesis of rhodamine derivatives (Hellmut & Lamm, 1977; Minru et al., 1977; Yojiro et al., 1992; Lee et al., 1998). 2-Carboxyl-4'-diethylamino-2'-hydroxybenzophenone was synthesized (Luo et al., 1994) from 3-diethylaminophenol and phthalic anhydride in toluene with the same reaction mechanism as the title compound. In the present paper, the title compound has been synthesized and the crystal structure of (I) is reported.

The bond distances and bond angles in (I) (Fig. 1) are similar to the corresponding dimensions reported for a closely related structure, 2-[4-(diethylamino)-2-hydroxybenzoyl]-3,4,5,6-tetrafluorobenzoic acid (Yan et al., 2006). The 2-hydroxy-4-dimethylaminobenzoyl and o-benzoic acid moieties in (I) are each essentially planar and the angle between two planes is 75.21 (5)°. There are intermolecular O—H···O hydrogen bonds involving the solvent and the complex molecules stabilizing the structure (Table 1 and Fig. 2). The structure also contains an intramolecular interaction of the type O—H···O (O···O = 2.589 (2) Å) and non-classical hydrogen bonds of the type C—H···O.

Experimental

A solution of 3-dimethylamino phenol (4.11 g, 30.0 mmol) and phthalic anhydride (4.66 g, 31.5 mmol) in toluene (30 ml) was refluxed for 3 h. The solution was cooled to room temperature and the precipitate was collected to afford the title compound (yield = 75.6%). The crude product was purified by silica-gel chromatography (methanol–dichloromethane, 1:50). Crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution in methanol and dichloromethane (5:1).