3-Nitro-N-(8-quinol­yl)benzamide

Gang Lei; Lin-Hai Jing; Li Zhou

doi:10.1107/S1600536808037811

. 2008 Nov 20;64(Pt 12):o2393. doi: 10.1107/S1600536808037811

3-Nitro-N-(8-quinolyl)benzamide

Gang Lei ^a,^*, Lin-Hai Jing ^a, Li Zhou ^a

PMCID: PMC2960006 PMID: 21581363

Abstract

The title compound, C₁₆H₁₁N₃O₃, crystallizes with two independent molecules which are almost identical to each other in the asymmetric unit. The dihedral angle between the quinoline ring system and the nitrobenzene ring is 51.04 (9)° in one of the molecules and 48.91 (9)° in the other. The crystal packing is stabilized by C—H⋯O hydrogen bonds and π–π interactions, with a centroid–centroid distance of 3.6010 (15) Å.

Related literature

For general background, see: Oku et al. (1998 ▶, 1999 ▶). For a related structure, see: Lei et al. (2008 ▶).

Experimental

Crystal data

C₁₆H₁₁N₃O₃
M _r = 293.28
Monoclinic,
a = 7.3783 (14) Å
b = 23.878 (5) Å
c = 7.4371 (14) Å
β = 90.775 (3)°
V = 1310.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 93 (2) K
0.40 × 0.30 × 0.23 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: none
10838 measured reflections
3071 independent reflections
2860 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.075
S = 1.14
3071 reflections
397 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: RAPID-AUTO (Rigaku, 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808037811/ci2717sup1.cif

e-64-o2393-sup1.cif^{(25.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037811/ci2717Isup2.hkl

e-64-o2393-Isup2.hkl^{(150.7KB, 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
C2—H2⋯O2ⁱ	0.95	2.56	3.395 (3)	147
C2A—H2A⋯O2ⁱ	0.95	2.50	3.346 (3)	148
C4—H4⋯O2Aⁱ	0.95	2.48	3.317 (3)	146
C16—H16⋯O3Aⁱⁱ	0.95	2.46	3.147 (3)	130
C16A—H16A⋯O1ⁱⁱⁱ	0.95	2.50	3.198 (3)	130
C17—H17⋯O1A^iv	0.95	2.45	3.396 (3)	172

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

Acknowledgments

The authors thank the Centre for Testing and Analysis, Cheng Du Branch, Chinese Academy of Sciences, for analytical support.

supplementary crystallographic information

Comment

Quinoline derivatives are important compounds for the treatment of bone metabolic disorders (Oku et al., 1998) and as H⁺-ATPases inhibitors (Oku et al., 1999). Previously, we have reported the crystal structure of (2-nitrophenyl)-N-(8-quinolyl)carboxamide (Lei et al., 2008). Now, we report here the crystal structure of the title compound.

The asymmetric unit of the title compound contains two independent molecules (Fig. 1) almost identical to each other in structure. Bond lengths and angles of the two molecules agree with each other and are comparable to those observed for (2-nitrophenyl)-N-(8-quinolyl)carboxamide (Lei et al., 2008). The quinoline ring systems are planar, with a maximum deviation of 0.017 (5) Å for atom C8 and 0.008 (5) Å for atom C9A, respectively. As a result of steric effects, the amide groups are twisted away from the planes of the quinoline benzene rings and 2-nitro substituted benzene rings (Fig. 1). The C5-C10 and C12-C17 planes form dihedral angles of 18.67 (1) and 32.89 (1)°, respectively, with the O1/N2/C8/C11 plane. Similarly, the C5A—C10A and C12A—C17A planes form dihedral angles of 20.90 (1) and 28.46 (1)°, respectively, with the O1A/N2A/C8A/C11A plane. The dihedral angle between C12-C17 and O2/O3/N3/C14 planes is 1.07 (1)° and that between C12A—C17A and O2A/O3A/N3A/C14A planes is 2.28 (1)°. The dihedral angle between quinoline ring system and nitrobenzene ring is 51.04 (9)° in one of the molecules and 48.91 (9)° in the other (with suffix A).

The crystal packing is stabilized by C—H···O hydrogen bonds (Table 1) and π-π interactionS involving C5A—C10A (centroid Cg1) and C12—C17 (centroid Cg2) benzene rings, with a Cg1···Cg2 distance of 3.6010 (15) Å.

Experimental

m-Nitrobenzoic acid (2 mmol) and an excess of thionyl chloride (3 mmol) in dioxane (20 ml) were boiled under reflux for 6 h. The solution was distilled under reduced pressure and a yellow solid was obtained. 8-Aminoquinoline (2 mmol) in tetrahydrofuran (20 ml) was added to the yellow solid and boiled under reflux for 6 h. The solution was then cooled to ambient temperature and filtered to remove the tetrahydrofuran. The precipitate was dissolved in dimethyl sulfoxide and the solution was allowed to stand for one month at ambient temperature, after which time white single crystals of the title compound suitable for X-ray diffraction were obtained.