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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 12| December 2008| Page o2401
doi:10.1107/S1600536808038038

4-Nitro-N-(8-quinol­yl)benzamide

Gang Lei,a* Lin-Hai Jinga and Li Zhoua

aSchool of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
*Correspondence e-mail: leigang307@yahoo.com.cn

(Received 14 November 2008; accepted 16 November 2008; online 20 November 2008)

In the title compound, C16H11N3O3, the amide group is twisted away from the plane of the quinoline benzene ring by 3.93 (5)°, but is twisted away from the nitro­benzene ring by 22.68 (4)°. A weak intra­molecular C—H⋯O hydrogen bond is observed. In the crystal structure, mol­ecules are linked into a chain along the a axis by inter­molecular C—H⋯O hydrogen bonds.

Related literature

For general background, see: Daoud et al. (2000[Daoud, R., Desneves, J., Deady, L.-W., Tilley, L., Scheper, R.-J., Gros, P. & Georges, E. (2000). Biochemistry, pp. 6094-6102.]); Westaway et al. (2006[Westaway, S.-M., Chung, Y.-K., Davis, J.-B., Holland, V., Jerman, J.-C., Medhurst, S.-J., Rami, H.-K., Stemp, G., Stevens, A.-J., Thompson, M., Winborn, K.-Y. & Wright, J. (2006). Bioorg. Med. Chem. Lett. pp. 4533-4536.]). For related structures, see: Lei et al. (2008a[Lei, G., Jing, L.-H. & Zhou, L. (2008a). Acta Cryst. E64, o2392.],b[Lei, G., Jing, L.-H. & Zhou, L. (2008b). Acta Cryst. E64, o2393.]).

[Scheme 1]

Experimental

Crystal data

  • C16H11N3O3

  • Mr = 293.28

  • Monoclinic, P 21 /c

  • a = 7.5230 (15) Å

  • b = 25.031 (5) Å

  • c = 6.9596 (15) Å

  • β = 100.081 (3)°

  • V = 1290.3 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 93 (2) K

  • 0.43 × 0.30 × 0.15 mm
Data collection

  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: none

  • 10531 measured reflections

  • 2905 independent reflections

  • 2542 reflections with I > 2σ(I)

  • Rint = 0.030
Refinement

  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.135

  • S = 1.00

  • 2905 reflections

  • 199 parameters

  • H-atom parameters constrained

  • Δρmax = 0.27 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C7—H7⋯O1 0.95 2.26 2.8672 (19) 121
C14—H14⋯O1i 0.95 2.34 3.2483 (18) 160
C17—H17⋯O3ii 0.95 2.38 3.3050 (18) 163
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z.

Data collection: RAPID-AUTO (Rigaku, 2004[Rigaku (2004). RAPID-AUTO. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038038/ci2725sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808038038/ci2725Isup2.hkl

checkCIF report


Comment top

Quinoline derivatives are a class of important compound as antagonists of TRPV1 (Westaway et al., 2006) and a sensitive and specific probe for studying MRP-drug interactions (Daoud et al., 2000). Previously, we have reported the crystal structures of (2-nitrophenyl)-N-(8-quinolyl)carboxamide (Lei et al., 2008a) and (3-nitrophenyl)-N-(8-quinolyl)carboxamide (Lei et al., 2008b). Now, we report here the crystal structure of the title compound (Fig.1).

Bond lengths and angles are normal. The quinoline ring system is planar, with a maximum deviation of 0.010 (7) Å for atom C5. As observed in related structures (Lei et al., 2008a,b), the amide group is twisted away from the planes of the quinoline benzene ring and 4-nitro substituted benzene ring. The C5—C10 and C12—C17 planes form dihedral angles of 3.93 (5)° and 22.68 (4)°, respectively, with the O1/N2/C8/C11 plane. The C12—C17 and O2/O3/N3/C15 planes are inclined at an angle of 2.58 (7)°. The dihedral angle between the N1/C2-C10 and C12-C17 planes is 26.36 (3)°. An intramolecular C7—H7···O1 hydrogen bond is observed.

The crystal packing is stabilized by C—H···O hydrogen bonds (Table 1). These hydrogen bonds link the molecules into a chain along the a axis.

Related literature top

For general background, see: Daoud et al. (2000); Westaway et al. (2006). For related structures, see: Lei et al. (2008a,b).

Experimental top

p-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 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.

Refinement top

All H atoms were placed in calculated positions, with C-H = 0.95 Å and N-H = 0.88 Å, and refined using a riding model, with Uiso(H) = 1.2Ueq(C,N).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO (Rigaku, 2004); data reduction: RAPID-AUTO (Rigaku, 2004); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering.
4-Nitro-N-(8-quinolyl)benzamide top
Crystal data top
C16H11N3O3F(000) = 608
Mr = 293.28Dx = 1.510 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3970 reflections
a = 7.5230 (15) Åθ = 3.1–27.5°
b = 25.031 (5) ŵ = 0.11 mm−1
c = 6.9596 (15) ÅT = 93 K
β = 100.081 (3)°Block, white
V = 1290.3 (5) Å30.43 × 0.30 × 0.15 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer		2542 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.030
Graphite monochromatorθmax = 27.5°, θmin = 3.1°
ω scansh = −9→9
10531 measured reflectionsk = −32→21
2905 independent reflectionsl = −9→9
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0868P)2 + 0.086P]
where P = (Fo2 + 2Fc2)/3
2905 reflections(Δ/σ)max = 0.001
199 parametersΔρmax = 0.27 e Å−3
0 restraintsΔρmin = −0.27 e Å−3
Crystal data top
C16H11N3O3V = 1290.3 (5) Å3
Mr = 293.28Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.5230 (15) ŵ = 0.11 mm−1
b = 25.031 (5) ÅT = 93 K
c = 6.9596 (15) Å0.43 × 0.30 × 0.15 mm
β = 100.081 (3)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer		2542 reflections with I > 2σ(I)
10531 measured reflectionsRint = 0.030
2905 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.135H-atom parameters constrained
S = 1.00Δρmax = 0.27 e Å−3
2905 reflectionsΔρmin = −0.27 e Å−3
199 parameters
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 > σ(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
xyzUiso*/Ueq
O10.69786 (14)0.38934 (4)0.50464 (16)0.0233 (3)
O2−0.00273 (15)0.55640 (4)0.15111 (17)0.0268 (3)
O3−0.19660 (14)0.49876 (4)0.22148 (16)0.0286 (3)
N10.38108 (16)0.21834 (5)0.42312 (18)0.0192 (3)
N20.51347 (16)0.31652 (5)0.46574 (18)0.0188 (3)
H2N0.39930.30690.43970.023*
N3−0.04073 (16)0.51288 (5)0.21646 (18)0.0202 (3)
C20.3131 (2)0.16969 (6)0.3996 (2)0.0220 (3)
H20.18600.16630.36190.026*
C30.4163 (2)0.12257 (6)0.4267 (2)0.0225 (3)
H30.36000.08860.40730.027*
C40.5990 (2)0.12671 (6)0.4816 (2)0.0212 (3)
H40.67130.09540.50170.025*
C50.8683 (2)0.18552 (6)0.5631 (2)0.0208 (3)
H50.94730.15560.58200.025*
C60.9366 (2)0.23613 (6)0.5891 (2)0.0212 (3)
H61.06310.24100.62730.025*
C70.8229 (2)0.28130 (6)0.5603 (2)0.0199 (3)
H70.87290.31610.58030.024*
C80.64030 (19)0.27499 (5)0.5036 (2)0.0170 (3)
C90.56440 (19)0.22250 (5)0.4778 (2)0.0172 (3)
C100.6807 (2)0.17763 (6)0.5084 (2)0.0187 (3)
C110.54650 (19)0.36987 (6)0.4646 (2)0.0183 (3)
C120.38470 (19)0.40539 (5)0.4061 (2)0.0176 (3)
C130.2074 (2)0.39106 (6)0.4189 (2)0.0192 (3)
H130.18330.35690.46790.023*
C140.06669 (19)0.42655 (6)0.3603 (2)0.0196 (3)
H14−0.05400.41740.36980.023*
C150.10717 (18)0.47577 (6)0.2876 (2)0.0177 (3)
C160.2814 (2)0.49139 (6)0.2769 (2)0.0197 (3)
H160.30510.52580.22950.024*
C170.4202 (2)0.45575 (6)0.3369 (2)0.0194 (3)
H170.54100.46570.33080.023*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0184 (5)0.0193 (5)0.0318 (6)−0.0021 (4)0.0033 (5)0.0004 (4)
O20.0276 (6)0.0197 (6)0.0326 (6)0.0013 (4)0.0041 (5)0.0062 (5)
O30.0170 (6)0.0307 (6)0.0390 (7)0.0022 (4)0.0079 (5)0.0071 (5)
N10.0178 (6)0.0208 (6)0.0201 (6)−0.0022 (5)0.0061 (5)−0.0010 (5)
N20.0153 (6)0.0159 (6)0.0255 (7)0.0000 (4)0.0045 (5)−0.0006 (5)
N30.0199 (6)0.0209 (6)0.0202 (6)0.0015 (5)0.0049 (5)−0.0005 (5)
C20.0219 (8)0.0245 (8)0.0201 (8)−0.0037 (6)0.0055 (6)−0.0010 (6)
C30.0285 (8)0.0194 (7)0.0201 (7)−0.0043 (6)0.0055 (6)−0.0016 (6)
C40.0275 (8)0.0183 (7)0.0190 (7)0.0024 (6)0.0073 (6)0.0004 (6)
C50.0205 (7)0.0221 (7)0.0198 (7)0.0055 (6)0.0037 (6)0.0022 (6)
C60.0181 (7)0.0252 (8)0.0207 (7)0.0023 (6)0.0044 (6)0.0013 (6)
C70.0213 (7)0.0194 (7)0.0198 (7)−0.0020 (6)0.0053 (6)−0.0009 (6)
C80.0180 (7)0.0183 (7)0.0157 (7)0.0022 (5)0.0056 (6)0.0001 (5)
C90.0179 (7)0.0195 (7)0.0150 (7)0.0011 (5)0.0051 (6)−0.0004 (5)
C100.0224 (7)0.0201 (7)0.0144 (7)0.0011 (6)0.0054 (6)0.0007 (5)
C110.0194 (7)0.0186 (7)0.0173 (7)−0.0009 (6)0.0047 (6)−0.0011 (5)
C120.0180 (7)0.0174 (7)0.0173 (7)−0.0012 (5)0.0033 (6)−0.0022 (5)
C130.0215 (7)0.0173 (7)0.0192 (7)−0.0011 (6)0.0041 (6)−0.0005 (6)
C140.0183 (7)0.0197 (7)0.0214 (7)−0.0013 (6)0.0055 (6)−0.0013 (6)
C150.0183 (7)0.0174 (7)0.0171 (7)0.0025 (5)0.0022 (6)−0.0010 (5)
C160.0224 (8)0.0173 (7)0.0196 (7)−0.0032 (6)0.0046 (6)0.0004 (6)
C170.0190 (7)0.0188 (7)0.0210 (7)−0.0024 (6)0.0047 (6)−0.0012 (6)
Geometric parameters (Å, º) top
O1—C111.2250 (17)C6—C71.411 (2)
O2—N31.2332 (15)C6—H60.95
O3—N31.2311 (16)C7—C81.370 (2)
N1—C21.3198 (18)C7—H70.95
N1—C91.3689 (18)C8—C91.4311 (19)
N2—C111.3587 (18)C9—C101.4166 (19)
N2—C81.4045 (17)C11—C121.505 (2)
N2—H2N0.88C12—C171.3921 (19)
N3—C151.4673 (18)C12—C131.399 (2)
C2—C31.406 (2)C13—C141.388 (2)
C2—H20.95C13—H130.95
C3—C41.365 (2)C14—C151.386 (2)
C3—H30.95C14—H140.95
C4—C101.413 (2)C15—C161.382 (2)
C4—H40.95C16—C171.381 (2)
C5—C61.367 (2)C16—H160.95
C5—C101.410 (2)C17—H170.95
C5—H50.95
C2—N1—C9117.02 (12)N1—C9—C10123.15 (13)
C11—N2—C8127.57 (12)N1—C9—C8117.72 (12)
C11—N2—H2N116.2C10—C9—C8119.12 (13)
C8—N2—H2N116.2C5—C10—C4123.60 (13)
O3—N3—O2123.20 (12)C5—C10—C9119.48 (13)
O3—N3—C15118.58 (12)C4—C10—C9116.93 (14)
O2—N3—C15118.20 (12)O1—C11—N2123.60 (14)
N1—C2—C3124.36 (14)O1—C11—C12120.14 (13)
N1—C2—H2117.8N2—C11—C12116.24 (12)
C3—C2—H2117.8C17—C12—C13119.82 (13)
C4—C3—C2118.62 (14)C17—C12—C11115.68 (13)
C4—C3—H3120.7C13—C12—C11124.50 (13)
C2—C3—H3120.7C14—C13—C12120.28 (13)
C3—C4—C10119.91 (14)C14—C13—H13119.9
C3—C4—H4120.0C12—C13—H13119.9
C10—C4—H4120.0C15—C14—C13118.12 (13)
C6—C5—C10120.06 (13)C15—C14—H14120.9
C6—C5—H5120.0C13—C14—H14120.9
C10—C5—H5120.0C16—C15—C14122.82 (13)
C5—C6—C7121.27 (14)C16—C15—N3118.23 (13)
C5—C6—H6119.4C14—C15—N3118.94 (12)
C7—C6—H6119.4C17—C16—C15118.37 (13)
C8—C7—C6120.06 (13)C17—C16—H16120.8
C8—C7—H7120.0C15—C16—H16120.8
C6—C7—H7120.0C16—C17—C12120.56 (13)
C7—C8—N2125.63 (13)C16—C17—H17119.7
C7—C8—C9119.99 (12)C12—C17—H17119.7
N2—C8—C9114.38 (12)
C9—N1—C2—C3−0.1 (2)C8—C9—C10—C4179.81 (12)
N1—C2—C3—C40.2 (2)C8—N2—C11—O1−2.6 (2)
C2—C3—C4—C10−0.5 (2)C8—N2—C11—C12176.13 (12)
C10—C5—C6—C7−0.6 (2)O1—C11—C12—C1721.26 (19)
C5—C6—C7—C8−0.6 (2)N2—C11—C12—C17−157.50 (13)
C6—C7—C8—N2−178.40 (13)O1—C11—C12—C13−158.21 (14)
C6—C7—C8—C91.4 (2)N2—C11—C12—C1323.0 (2)
C11—N2—C8—C74.8 (2)C17—C12—C13—C140.9 (2)
C11—N2—C8—C9−174.98 (13)C11—C12—C13—C14−179.67 (13)
C2—N1—C9—C100.3 (2)C12—C13—C14—C150.7 (2)
C2—N1—C9—C8179.93 (12)C13—C14—C15—C16−2.1 (2)
C7—C8—C9—N1179.29 (12)C13—C14—C15—N3177.21 (12)
N2—C8—C9—N1−0.91 (19)O3—N3—C15—C16178.40 (13)
C7—C8—C9—C10−1.0 (2)O2—N3—C15—C16−0.28 (19)
N2—C8—C9—C10178.77 (12)O3—N3—C15—C14−0.90 (19)
C6—C5—C10—C4−178.98 (13)O2—N3—C15—C14−179.58 (13)
C6—C5—C10—C91.0 (2)C14—C15—C16—C171.7 (2)
C3—C4—C10—C5−179.42 (13)N3—C15—C16—C17−177.59 (12)
C3—C4—C10—C90.6 (2)C15—C16—C17—C120.0 (2)
N1—C9—C10—C5179.52 (12)C13—C12—C17—C16−1.3 (2)
C8—C9—C10—C5−0.1 (2)C11—C12—C17—C16179.23 (12)
N1—C9—C10—C4−0.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O10.952.262.8672 (19)121
C14—H14···O1i0.952.343.2483 (18)160
C17—H17···O3ii0.952.383.3050 (18)163
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC16H11N3O3
Mr293.28
Crystal system, space groupMonoclinic, P21/c
Temperature (K)93
a, b, c (Å)7.5230 (15), 25.031 (5), 6.9596 (15)
β (°) 100.081 (3)
V (Å3)1290.3 (5)
Z4
Radiation typeMo Kα
µ (mm−1)0.11
Crystal size (mm)0.43 × 0.30 × 0.15
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		10531, 2905, 2542
Rint0.030
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.135, 1.00
No. of reflections2905
No. of parameters199
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.27, −0.27

Computer programs: RAPID-AUTO (Rigaku, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O10.952.262.8672 (19)121
C14—H14···O1i0.952.343.2483 (18)160
C17—H17···O3ii0.952.383.3050 (18)163
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z.
 

Acknowledgements

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

References

First citationDaoud, R., Desneves, J., Deady, L.-W., Tilley, L., Scheper, R.-J., Gros, P. & Georges, E. (2000). Biochemistry, pp. 6094–6102.  Web of Science CrossRef Google Scholar
 First citationLei, G., Jing, L.-H. & Zhou, L. (2008a). Acta Cryst. E64, o2392.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationLei, G., Jing, L.-H. & Zhou, L. (2008b). Acta Cryst. E64, o2393.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationRigaku (2004). RAPID-AUTO. Rigaku/MSC Inc., The Woodlands, Texas, USA.  Google Scholar
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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 12| December 2008| Page o2401
doi:10.1107/S1600536808038038
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