4-Chloro­benzoic acid–quinoline (1/1)

Kazuma Gotoh; Kaori Katagiri; Hiroyuki Ishida

doi:10.1107/S1600536810046416

. 2010 Nov 17;66(Pt 12):o3190. doi: 10.1107/S1600536810046416

4-Chlorobenzoic acid–quinoline (1/1)

Kazuma Gotoh ^a, Kaori Katagiri ^a, Hiroyuki Ishida ^a,^*

PMCID: PMC3011561 PMID: 21589484

Abstract

In the title compound, C₇H₅ClO₂·C₉H₇N, the 4-chlorobenzoic acid molecule is almost planar, with a dihedral angle of 2.9 (14)° between the carboxy group and the benzene ring. In the crystal, the two components are connected by an O—H⋯N hydrogen bond. In the hydrogen-bonded unit, the dihedral angle between the quinoline ring system and the benzene ring of the benzoic acid is 44.75 (4)°. The two components are further linked by intermolecular C—H⋯O hydrogen bonds, forming a layer parallel to the ab plane.

Related literature

For related structures, see, for example: Gotoh & Ishida (2007 ▶, 2009 ▶); Ishida & Fukunaga (2004 ▶).

Experimental

Crystal data

C₇H₅ClO₂·C₉H₇N
M _r = 285.73
Orthorhombic,
a = 13.2385 (5) Å
b = 3.8307 (2) Å
c = 26.2464 (9) Å
V = 1331.03 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 185 K
0.30 × 0.26 × 0.18 mm

Data collection

Rigaku R-AXIS RAPID II diffractometer
Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T _min = 0.933, T _max = 0.950
21775 measured reflections
3907 independent reflections
3777 reflections with I > 2σ(I)
R _int = 0.017

Refinement

R[F ² > 2σ(F ²)] = 0.027
wR(F ²) = 0.071
S = 1.07
3907 reflections
185 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.15 e Å⁻³
Absolute structure: Flack (1983 ▶), 1909 Friedel pairs
Flack parameter: 0.03 (4)

Data collection: PROCESS-AUTO (Rigaku/MSC, 2004 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997) ▶; software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810046416/im2244sup1.cif

e-66-o3190-sup1.cif^{(17.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046416/im2244Isup2.hkl

e-66-o3190-Isup2.hkl^{(191.5KB, 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⋯N1	0.84 (2)	1.82 (2)	2.659 (1)	176 (2)
C5—H5⋯O2ⁱ	0.95	2.46	3.159 (1)	130
C8—H8⋯O2ⁱⁱ	0.95	2.57	3.252 (2)	129

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

Acknowledgments

This work was supported by a Grant-in-Aid for Scientific Research (C) (No. 22550013) from the Japan Society for the Promotion of Science.

supplementary crystallographic information

Comment

The title compound was prepared in order to extend our study on D—H···A hydrogen bonding (D = N, O, or C; A = N, O or Cl) in amine–benzoic acid systems (Gotoh & Ishida, 2007, 2009; Ishida & Fukunaga, 2004).

In the crystal structure of the title compound, no acid-base interaction involving proton transfer is observed between the two components, which are are linked by an O—H···N hydrogen bond (Table 1 and Fig. 1). In the hydrogen-bonded unit, the dihedral angle between the quinoline ring system and the benzene ring of the benzoic acid is 44.75 (4)°. The carboxy plane makes dihedral angles of 42.2 (1) and 2.9 (14)°, respectively, with the quinoline ring system and the benzene ring. The two components are further linked by intermolecular C—H···O hydrogen bonds (Table 1), forming a layer parallel to the ab plane (Fig. 2). No significant interaction is observed between the layers.

Experimental

Single crystals were obtained by slow evaporation from an acetonitrile solution (65 ml) of 4-chlorobenzoic acid (156 mg) and quinoline (167 mg) at room temperature.