Literature DB >> 21581362

2-Nitro-N-(8-quinolyl)benzamide.

Gang Lei1, Lin-Hai Jing, Li Zhou.   

Abstract

In the title compound, C(16)H(11)N(3)O(3), the amide group is twisted away from the quinoline ring system and nitro-benzene ring by 8.02 (1)° and 54.92 (1)°, respectively. The crystal packing is stabilized by inter-molecular C-H⋯O hydrogen bonds, and π-π inter-actions between the quinoline ring systems of inversion-related mol-ecules, with a centroid-centroid distance of 3.4802 (13) Å.

Entities:  

Year:  2008        PMID： 21581362      PMCID： PMC2959943          DOI： 10.1107/S160053680803777X

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the biological activities of quinoline derivatives, see: Oku et al. (1998 ▶, 1999 ▶).

Experimental

Crystal data

C16H11N3O3 M = 293.28 Monoclinic, a = 12.430 (3) Å b = 10.144 (3) Å c = 11.528 (3) Å β = 116.449 (3)° V = 1301.4 (6) Å3 Z = 4 Mo Kα radiation μ = 0.11 mm−1 T = 93 (2) K 0.50 × 0.40 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID diffractometer Absorption correction: none 10410 measured reflections 2949 independent reflections 2679 reflections with I > 2σ(I) R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.051 wR(F 2) = 0.145 S = 1.00 2949 reflections 199 parameters H-atom parameters constrained Δρmax = 0.22 e Å−3 Δρmin = −0.28 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. Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680803777X/ci2716sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S160053680803777X/ci2716Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C16H11N3O3F000 = 608
Mr = 293.28Dx = 1.497 Mg m−3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3984 reflections
a = 12.430 (3) Åθ = 3.2–27.5º
b = 10.144 (3) ŵ = 0.11 mm−1
c = 11.528 (3) ÅT = 93 (2) K
β = 116.449 (3)ºBlock, white
V = 1301.4 (6) Å30.50 × 0.40 × 0.15 mm
Z = 4
Rigaku R-AXIS RAPID diffractometer2679 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.029
Monochromator: graphiteθmax = 27.5º
T = 93(2) Kθmin = 3.5º
ω scansh = −16→16
Absorption correction: nonek = −12→13
10410 measured reflectionsl = −14→11
2949 independent reflections
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.145  w = 1/[σ2(Fo2) + (0.089P)2 + 0.36P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.005
2949 reflectionsΔρmax = 0.22 e Å−3
199 parametersΔρmin = −0.28 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
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.
xyzUiso*/Ueq
O10.33297 (10)0.27884 (13)0.71053 (11)0.0283 (3)
O20.42529 (10)0.55360 (12)0.75700 (12)0.0290 (3)
O30.60516 (11)0.50766 (12)0.90418 (11)0.0291 (3)
N10.07416 (11)0.46239 (13)0.28513 (13)0.0202 (3)
N20.23340 (11)0.35402 (13)0.50283 (13)0.0201 (3)
H2N0.24600.38350.43810.024*
N30.52329 (11)0.49852 (13)0.79419 (13)0.0213 (3)
C2−0.00265 (14)0.52243 (15)0.17885 (15)0.0212 (3)
H20.02840.56710.12780.025*
C3−0.12782 (14)0.52428 (15)0.13644 (16)0.0223 (4)
H3−0.17910.56910.05900.027*
C4−0.17449 (14)0.46062 (15)0.20824 (16)0.0221 (4)
H4−0.25880.45910.18030.027*
C5−0.13518 (14)0.33419 (15)0.40878 (16)0.0210 (3)
H5−0.21840.32980.38650.025*
C6−0.05278 (14)0.27986 (15)0.52209 (16)0.0215 (3)
H6−0.08000.23880.57830.026*
C70.07210 (14)0.28306 (15)0.55819 (16)0.0205 (3)
H70.12750.24410.63730.025*
C80.11263 (13)0.34276 (14)0.47822 (15)0.0187 (3)
C90.02839 (13)0.40129 (14)0.35897 (15)0.0181 (3)
C10−0.09602 (13)0.39701 (15)0.32465 (15)0.0194 (3)
C110.33334 (13)0.32539 (15)0.61325 (15)0.0197 (3)
C120.44935 (13)0.34895 (15)0.60488 (14)0.0184 (3)
C130.54399 (13)0.41992 (15)0.69958 (15)0.0189 (3)
C140.65666 (14)0.42618 (15)0.70338 (16)0.0220 (3)
H140.71980.47410.76980.026*
C150.67563 (14)0.36117 (15)0.60838 (17)0.0243 (4)
H150.75270.36290.61000.029*
C160.58228 (15)0.29374 (16)0.51112 (16)0.0239 (4)
H160.59510.25180.44470.029*
C170.47000 (14)0.28663 (15)0.50942 (15)0.0216 (3)
H170.40700.23890.44260.026*
U11U22U33U12U13U23
O10.0213 (6)0.0419 (7)0.0199 (6)−0.0011 (5)0.0074 (5)0.0064 (5)
O20.0197 (6)0.0347 (7)0.0308 (7)0.0053 (5)0.0098 (5)−0.0042 (5)
O30.0255 (6)0.0327 (7)0.0207 (6)−0.0014 (5)0.0026 (5)−0.0051 (5)
N10.0183 (6)0.0203 (6)0.0204 (7)−0.0013 (5)0.0073 (5)0.0005 (5)
N20.0168 (6)0.0242 (7)0.0187 (7)−0.0022 (5)0.0074 (5)0.0018 (5)
N30.0191 (6)0.0210 (7)0.0213 (7)−0.0014 (5)0.0067 (6)−0.0016 (5)
C20.0218 (8)0.0205 (7)0.0200 (8)−0.0014 (6)0.0081 (6)0.0023 (6)
C30.0201 (7)0.0195 (7)0.0229 (8)0.0002 (6)0.0056 (6)0.0004 (6)
C40.0174 (7)0.0197 (7)0.0267 (9)0.0012 (6)0.0076 (6)−0.0010 (6)
C50.0181 (7)0.0197 (7)0.0271 (8)−0.0013 (6)0.0118 (6)−0.0031 (6)
C60.0244 (8)0.0186 (7)0.0259 (9)−0.0027 (6)0.0151 (7)−0.0014 (6)
C70.0213 (8)0.0188 (7)0.0211 (8)−0.0005 (6)0.0092 (6)−0.0016 (6)
C80.0169 (7)0.0167 (7)0.0216 (8)−0.0023 (5)0.0079 (6)−0.0034 (6)
C90.0184 (7)0.0156 (7)0.0196 (8)−0.0014 (5)0.0078 (6)−0.0024 (6)
C100.0184 (7)0.0165 (7)0.0219 (8)−0.0010 (5)0.0077 (6)−0.0039 (6)
C110.0193 (7)0.0199 (7)0.0188 (8)−0.0008 (6)0.0076 (6)−0.0015 (6)
C120.0171 (7)0.0189 (7)0.0165 (7)0.0014 (5)0.0050 (6)0.0040 (5)
C130.0188 (7)0.0181 (7)0.0180 (8)0.0014 (5)0.0066 (6)0.0013 (6)
C140.0165 (7)0.0205 (7)0.0259 (8)−0.0006 (6)0.0065 (6)0.0007 (6)
C150.0216 (8)0.0207 (7)0.0328 (9)0.0030 (6)0.0140 (7)0.0049 (7)
C160.0281 (8)0.0219 (8)0.0249 (9)0.0015 (6)0.0148 (7)0.0021 (6)
C170.0225 (8)0.0223 (8)0.0189 (8)−0.0012 (6)0.0081 (6)0.0009 (6)
O1—C111.219 (2)C6—C71.417 (2)
O2—N31.2307 (17)C6—H60.95
O3—N31.2257 (17)C7—C81.373 (2)
N1—C21.320 (2)C7—H70.95
N1—C91.365 (2)C8—C91.434 (2)
N2—C111.3562 (19)C9—C101.416 (2)
N2—C81.4028 (19)C11—C121.507 (2)
N2—H2N0.88C12—C171.389 (2)
N3—C131.463 (2)C12—C131.396 (2)
C2—C31.408 (2)C13—C141.383 (2)
C2—H20.95C14—C151.386 (2)
C3—C41.366 (2)C14—H140.95
C3—H30.95C15—C161.383 (2)
C4—C101.415 (2)C15—H150.95
C4—H40.95C16—C171.389 (2)
C5—C61.366 (2)C16—H160.95
C5—C101.416 (2)C17—H170.95
C5—H50.95
C2—N1—C9117.28 (13)N1—C9—C10123.11 (14)
C11—N2—C8128.52 (13)N1—C9—C8117.16 (13)
C11—N2—H2N115.7C10—C9—C8119.70 (14)
C8—N2—H2N115.7C4—C10—C5123.56 (14)
O3—N3—O2124.26 (14)C4—C10—C9117.17 (14)
O3—N3—C13118.14 (13)C5—C10—C9119.23 (14)
O2—N3—C13117.59 (13)O1—C11—N2124.71 (14)
N1—C2—C3123.99 (15)O1—C11—C12121.09 (14)
N1—C2—H2118.0N2—C11—C12114.12 (13)
C3—C2—H2118.0C17—C12—C13117.75 (14)
C4—C3—C2119.02 (15)C17—C12—C11119.90 (13)
C4—C3—H3120.5C13—C12—C11121.93 (14)
C2—C3—H3120.5C14—C13—C12122.48 (15)
C3—C4—C10119.39 (14)C14—C13—N3117.59 (13)
C3—C4—H4120.3C12—C13—N3119.80 (13)
C10—C4—H4120.3C13—C14—C15118.66 (14)
C6—C5—C10119.76 (14)C13—C14—H14120.7
C6—C5—H5120.1C15—C14—H14120.7
C10—C5—H5120.1C16—C15—C14119.96 (15)
C5—C6—C7121.88 (15)C16—C15—H15120.0
C5—C6—H6119.1C14—C15—H15120.0
C7—C6—H6119.1C15—C16—C17120.81 (15)
C8—C7—C6119.64 (15)C15—C16—H16119.6
C8—C7—H7120.2C17—C16—H16119.6
C6—C7—H7120.2C12—C17—C16120.29 (15)
C7—C8—N2125.45 (14)C12—C17—H17119.9
C7—C8—C9119.78 (14)C16—C17—H17119.9
N2—C8—C9114.76 (13)
C9—N1—C2—C3−1.5 (2)C8—C9—C10—C5−0.3 (2)
N1—C2—C3—C40.0 (2)C8—N2—C11—O13.0 (3)
C2—C3—C4—C101.4 (2)C8—N2—C11—C12179.71 (14)
C10—C5—C6—C7−0.7 (2)O1—C11—C12—C17120.18 (17)
C5—C6—C7—C80.4 (2)N2—C11—C12—C17−56.67 (19)
C6—C7—C8—N2179.31 (14)O1—C11—C12—C13−52.2 (2)
C6—C7—C8—C90.0 (2)N2—C11—C12—C13130.96 (15)
C11—N2—C8—C7−9.2 (3)C17—C12—C13—C14−2.1 (2)
C11—N2—C8—C9170.17 (14)C11—C12—C13—C14170.39 (14)
C2—N1—C9—C101.7 (2)C17—C12—C13—N3173.65 (13)
C2—N1—C9—C8−176.46 (14)C11—C12—C13—N3−13.8 (2)
C7—C8—C9—N1178.25 (13)O3—N3—C13—C14−37.9 (2)
N2—C8—C9—N1−1.14 (19)O2—N3—C13—C14140.59 (15)
C7—C8—C9—C100.0 (2)O3—N3—C13—C12146.16 (15)
N2—C8—C9—C10−179.40 (13)O2—N3—C13—C12−35.4 (2)
C3—C4—C10—C5176.77 (14)C12—C13—C14—C151.0 (2)
C3—C4—C10—C9−1.2 (2)N3—C13—C14—C15−174.87 (13)
C6—C5—C10—C4−177.25 (15)C13—C14—C15—C161.1 (2)
C6—C5—C10—C90.6 (2)C14—C15—C16—C17−2.0 (2)
N1—C9—C10—C4−0.4 (2)C13—C12—C17—C161.2 (2)
C8—C9—C10—C4177.72 (13)C11—C12—C17—C16−171.51 (14)
N1—C9—C10—C5−178.44 (13)C15—C16—C17—C120.9 (2)
D—H···AD—HH···AD···AD—H···A
C3—H3···O3i0.952.553.209 (2)127
C4—H4···O2ii0.952.483.319 (2)147
C17—H17···O1iii0.952.423.160 (2)135
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C3—H3⋯O3i0.952.553.209 (2)127
C4—H4⋯O2ii0.952.483.319 (2)147
C17—H17⋯O1iii0.952.423.160 (2)135

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

  1 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290
  1 in total
  2 in total

1.  4-Nitro-N-(8-quinol-yl)benzamide.

Authors:  Gang Lei; Lin-Hai Jing; Li Zhou
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-11-20

2.  3-Nitro-N-(8-quinol-yl)benzamide.

Authors:  Gang Lei; Lin-Hai Jing; Li Zhou
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-11-20
  2 in total

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