2-Chloro-4-nitro­benzoic acid–quinoline (1/1)

Kazuma Gotoh; Hiroyuki Ishida

doi:10.1107/S160053681104075X

. 2011 Oct 8;67(Pt 11):o2883. doi: 10.1107/S160053681104075X

2-Chloro-4-nitrobenzoic acid–quinoline (1/1)

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

PMCID: PMC3247614 PMID: 22219919

Abstract

In the title compound, C₇H₄ClNO₄·C₉H₇N, 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 benzoic acid is 3.15 (7)°. In the crystal, units are linked by intermolecular C—H⋯O hydrogen bonds, forming a tape along the c axis. The tapes are stacked along the b axis through a C—H⋯O hydrogen bond into a layer parallel to the bc plane.

Related literature

For related structures, see: Gotoh & Ishida (2009 ▶); Gotoh et al. (2010 ▶).

Experimental

Crystal data

C₉H₇N·C₇H₄ClNO₄
M _r = 330.73
Orthorhombic,
a = 31.125 (3) Å
b = 3.7560 (3) Å
c = 12.3615 (12) Å
V = 1445.1 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 185 K
0.35 × 0.22 × 0.06 mm

Data collection

Rigaku R-AXIS RAPID II diffractometer
Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T _min = 0.925, T _max = 0.983
17044 measured reflections
4166 independent reflections
3681 reflections with I > 2σ(I)
R _int = 0.053

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.083
S = 1.06
4166 reflections
212 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.25 e Å⁻³
Absolute structure: Flack (1983 ▶), 1989 Friedel pairs
Flack parameter: 0.01 (5)

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 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681104075X/lh5345sup1.cif

e-67-o2883-sup1.cif^{(17.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104075X/lh5345Isup2.hkl

e-67-o2883-Isup2.hkl^{(204.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681104075X/lh5345Isup3.cml

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⋯N2	0.95 (3)	1.65 (3)	2.595 (2)	177 (3)
C5—H5⋯O2ⁱ	0.95	2.44	3.251 (2)	143
C9—H9⋯O4ⁱⁱ	0.95	2.57	3.365 (3)	141
C14—H14⋯O3ⁱ	0.95	2.55	3.476 (3)	165

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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 quinoline–substituted benzoic acid systems (Gotoh & Ishida, 2009; Gotoh et al., 2010).

In the crystal structure of the title compound, no acid-base interaction involving proton transfer is observed between the two components, which 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 3.15 (7)°. The carboxyl plane makes dihedral angles of 43.0 (2) and 39.9 (2)°, 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 tape along the c axis and the tapes are stacked along the b axis through an C—H···O hydrogen bond into a layer parallel to the bc plane (Fig. 2). No significant interaction is observed between the layers.

Experimental

Single crystals were obtained by slow evaporation from an acetonitrile solution (30 ml) of 2-chloro-4-nitrobenzoic acid (233 mg) and quinoline (150 mg) at room temperature.