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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2393.
Published online 2008 November 20. doi:  10.1107/S1600536808037811
PMCID: PMC2960006

3-Nitro-N-(8-quinol­yl)benzamide

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 [triangle], 1999 [triangle]). For a related structure, see: Lei et al. (2008 [triangle]).

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Object name is e-64-o2393-scheme1.jpg

Experimental

Crystal data

  • C16H11N3O3
  • M r = 293.28
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2393-efi1.jpg
  • 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
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.19 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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.

Refinement

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). In the absence of significant anomalous scattering, Friedel pairs were merged prior to the final refinement.

Figures

Fig. 1.
The asymmetric unit of the title compound, showing two independent molecules. Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted for clarity.

Crystal data

C16H11N3O3F000 = 608
Mr = 293.28Dx = 1.487 Mg m3
Monoclinic, P21Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 4482 reflections
a = 7.3783 (14) Åθ = 3.2–27.5º
b = 23.878 (5) ŵ = 0.11 mm1
c = 7.4371 (14) ÅT = 93 (2) K
β = 90.775 (3)ºBlock, white
V = 1310.2 (4) Å30.40 × 0.30 × 0.23 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer2860 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.030
Monochromator: graphiteθmax = 27.5º
T = 93(2) Kθmin = 3.2º
ω scansh = −9→9
Absorption correction: nonek = −31→30
10838 measured reflectionsl = −9→9
3071 independent reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.075  w = 1/[σ2(Fo2) + (0.0354P)2] where P = (Fo2 + 2Fc2)/3
S = 1.14(Δ/σ)max = 0.001
3071 reflectionsΔρmax = 0.19 e Å3
397 parametersΔρmin = −0.19 e Å3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

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)

xyzUiso*/Ueq
O10.3802 (2)0.19096 (7)0.4467 (2)0.0229 (4)
O20.1871 (3)0.35241 (8)0.0594 (2)0.0334 (4)
O30.1573 (2)0.43422 (7)0.1784 (2)0.0308 (4)
N10.9400 (3)0.22508 (8)0.7724 (3)0.0202 (4)
N20.6102 (3)0.21775 (8)0.6364 (3)0.0195 (4)
H2N0.66000.24770.68500.023*
N30.2028 (3)0.38491 (8)0.1864 (3)0.0220 (4)
C21.1064 (3)0.23028 (11)0.8387 (3)0.0233 (5)
H21.15370.26700.85460.028*
C31.2169 (3)0.18492 (11)0.8868 (3)0.0263 (5)
H31.33650.19100.93150.032*
C41.1508 (3)0.13180 (11)0.8688 (3)0.0255 (5)
H41.22370.10060.90240.031*
C50.8918 (3)0.07037 (10)0.7766 (3)0.0224 (5)
H50.95670.03740.80820.027*
C60.7193 (3)0.06662 (10)0.7085 (3)0.0237 (5)
H60.66550.03070.69490.028*
C70.6189 (3)0.11439 (10)0.6579 (3)0.0218 (5)
H70.49970.11050.60970.026*
C80.6946 (3)0.16665 (9)0.6785 (3)0.0181 (5)
C90.8739 (3)0.17209 (9)0.7526 (3)0.0181 (5)
C100.9734 (3)0.12345 (10)0.7999 (3)0.0206 (5)
C110.4622 (3)0.22707 (10)0.5310 (3)0.0184 (5)
C120.4060 (3)0.28758 (9)0.5227 (3)0.0165 (5)
C130.3286 (3)0.30764 (9)0.3644 (3)0.0178 (5)
H130.31020.28360.26400.021*
C140.2792 (3)0.36325 (9)0.3560 (3)0.0169 (4)
C150.3002 (3)0.39973 (10)0.4987 (3)0.0205 (5)
H150.26540.43790.48830.025*
C160.3735 (3)0.37886 (10)0.6575 (3)0.0207 (5)
H160.38690.40270.75910.025*
C170.4276 (3)0.32341 (10)0.6691 (3)0.0188 (5)
H170.47980.30970.77790.023*
O1A0.6075 (2)0.26160 (7)0.0420 (2)0.0221 (4)
O2A0.4490 (2)0.06211 (8)0.1206 (3)0.0371 (5)
O3A0.6518 (3)0.00459 (8)0.2183 (3)0.0488 (6)
N1A0.8655 (3)0.35147 (8)0.5612 (2)0.0213 (4)
N2A0.7920 (3)0.29510 (8)0.2650 (3)0.0189 (4)
H2NA0.87550.28490.34400.023*
N3A0.6014 (3)0.05199 (8)0.1811 (3)0.0268 (5)
C2A0.9074 (3)0.37849 (11)0.7114 (3)0.0267 (6)
H2A0.95860.35780.80860.032*
C3A0.8798 (3)0.43636 (12)0.7346 (3)0.0299 (6)
H3A0.91320.45400.84460.036*
C4A0.8049 (3)0.46662 (11)0.5980 (3)0.0273 (6)
H4A0.78310.50550.61300.033*
C5A0.6826 (3)0.46776 (10)0.2831 (3)0.0241 (5)
H5A0.66030.50690.28810.029*
C6A0.6403 (3)0.43863 (10)0.1308 (3)0.0235 (5)
H6A0.58800.45780.03090.028*
C7A0.6729 (3)0.38034 (10)0.1186 (3)0.0217 (5)
H7A0.64200.36060.01150.026*
C8A0.7486 (3)0.35259 (9)0.2608 (3)0.0174 (5)
C9A0.7935 (3)0.38198 (10)0.4228 (3)0.0185 (5)
C10A0.7595 (3)0.44004 (10)0.4334 (3)0.0211 (5)
C11A0.7202 (3)0.25366 (10)0.1617 (3)0.0185 (5)
C12A0.7870 (3)0.19612 (10)0.2061 (3)0.0174 (5)
C13A0.6706 (3)0.15156 (10)0.1700 (3)0.0189 (5)
H13A0.55440.15780.11740.023*
C14A0.7274 (3)0.09834 (10)0.2121 (3)0.0194 (5)
C15A0.8969 (3)0.08665 (10)0.2844 (3)0.0231 (5)
H15A0.93260.04920.30990.028*
C16A1.0131 (3)0.13095 (10)0.3186 (3)0.0226 (5)
H16A1.13070.12420.36740.027*
C17A0.9574 (3)0.18545 (10)0.2814 (3)0.0204 (5)
H17A1.03660.21580.30770.025*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0230 (9)0.0215 (9)0.0242 (9)0.0012 (7)−0.0047 (7)−0.0039 (7)
O20.0457 (11)0.0319 (10)0.0223 (9)0.0074 (9)−0.0102 (8)−0.0034 (8)
O30.0382 (11)0.0207 (9)0.0333 (10)0.0058 (8)−0.0072 (8)0.0065 (8)
N10.0173 (10)0.0224 (10)0.0209 (10)−0.0028 (8)0.0014 (8)0.0017 (9)
N20.0215 (10)0.0154 (10)0.0214 (10)0.0025 (8)−0.0044 (8)−0.0030 (8)
N30.0189 (10)0.0249 (11)0.0222 (10)0.0011 (8)−0.0008 (8)0.0029 (9)
C20.0187 (11)0.0264 (14)0.0247 (13)−0.0039 (10)0.0010 (10)0.0014 (11)
C30.0187 (12)0.0359 (14)0.0242 (13)−0.0010 (11)−0.0007 (10)0.0016 (11)
C40.0209 (12)0.0329 (14)0.0228 (12)0.0065 (11)0.0003 (10)0.0021 (11)
C50.0242 (12)0.0197 (12)0.0233 (12)0.0043 (10)0.0008 (10)0.0020 (10)
C60.0298 (13)0.0166 (12)0.0248 (12)−0.0005 (10)0.0026 (10)−0.0013 (10)
C70.0222 (12)0.0198 (12)0.0233 (12)−0.0008 (9)−0.0003 (10)−0.0022 (10)
C80.0201 (11)0.0178 (11)0.0165 (11)0.0016 (9)0.0027 (9)0.0005 (9)
C90.0206 (11)0.0185 (12)0.0152 (11)0.0017 (9)0.0038 (9)0.0004 (9)
C100.0212 (12)0.0233 (12)0.0175 (12)0.0029 (10)0.0023 (9)0.0014 (10)
C110.0191 (11)0.0190 (11)0.0170 (11)−0.0009 (9)0.0010 (9)−0.0002 (10)
C120.0125 (10)0.0180 (11)0.0188 (11)−0.0009 (9)−0.0006 (9)−0.0001 (9)
C130.0144 (10)0.0196 (11)0.0195 (11)−0.0028 (9)0.0003 (9)−0.0022 (9)
C140.0135 (10)0.0207 (11)0.0166 (11)−0.0022 (8)−0.0011 (8)0.0043 (9)
C150.0185 (11)0.0177 (12)0.0252 (13)0.0001 (9)0.0023 (10)0.0009 (10)
C160.0224 (12)0.0186 (12)0.0212 (12)−0.0022 (9)0.0009 (10)−0.0022 (10)
C170.0164 (11)0.0219 (12)0.0181 (12)−0.0006 (9)0.0000 (9)0.0002 (9)
O1A0.0235 (8)0.0199 (8)0.0229 (9)0.0015 (7)−0.0048 (7)0.0002 (7)
O2A0.0302 (11)0.0256 (10)0.0551 (12)−0.0065 (8)−0.0173 (9)0.0057 (9)
O3A0.0509 (14)0.0158 (9)0.0787 (15)−0.0034 (9)−0.0272 (12)0.0107 (10)
N1A0.0175 (10)0.0261 (11)0.0203 (10)−0.0014 (8)−0.0005 (8)0.0019 (8)
N2A0.0182 (10)0.0166 (10)0.0216 (10)0.0010 (8)−0.0046 (8)0.0015 (8)
N3A0.0304 (12)0.0208 (11)0.0290 (12)−0.0007 (9)−0.0063 (10)0.0023 (9)
C2A0.0210 (12)0.0384 (15)0.0206 (12)−0.0023 (11)−0.0020 (10)−0.0013 (11)
C3A0.0277 (14)0.0364 (15)0.0257 (13)−0.0091 (12)0.0030 (11)−0.0106 (12)
C4A0.0229 (13)0.0242 (13)0.0347 (14)−0.0054 (10)0.0047 (11)−0.0061 (11)
C5A0.0189 (11)0.0170 (12)0.0365 (14)−0.0011 (9)0.0040 (10)0.0045 (10)
C6A0.0217 (12)0.0204 (12)0.0284 (13)0.0013 (10)−0.0020 (10)0.0076 (11)
C7A0.0214 (11)0.0214 (12)0.0224 (12)−0.0009 (9)0.0001 (10)0.0022 (10)
C8A0.0158 (10)0.0154 (11)0.0210 (12)−0.0009 (9)0.0019 (9)0.0012 (9)
C9A0.0144 (10)0.0198 (11)0.0214 (11)−0.0024 (9)0.0027 (9)0.0017 (9)
C10A0.0171 (11)0.0203 (12)0.0260 (12)−0.0032 (9)0.0029 (9)−0.0026 (10)
C11A0.0173 (11)0.0199 (12)0.0183 (12)0.0005 (9)0.0012 (10)−0.0001 (10)
C12A0.0192 (11)0.0165 (11)0.0164 (11)0.0001 (9)0.0015 (9)0.0005 (9)
C13A0.0224 (12)0.0203 (12)0.0138 (11)0.0016 (9)−0.0022 (9)0.0010 (9)
C14A0.0206 (11)0.0188 (12)0.0188 (11)−0.0016 (9)−0.0018 (9)0.0003 (9)
C15A0.0258 (12)0.0196 (12)0.0236 (13)0.0023 (10)−0.0026 (10)−0.0004 (10)
C16A0.0184 (12)0.0242 (13)0.0251 (12)0.0030 (10)−0.0038 (10)0.0006 (10)
C17A0.0184 (11)0.0218 (12)0.0211 (11)−0.0010 (9)0.0001 (9)−0.0006 (10)

Geometric parameters (Å, °)

O1—C111.222 (3)O1A—C11A1.224 (3)
O2—N31.227 (2)O2A—N3A1.230 (3)
O3—N31.225 (3)O3A—N3A1.222 (3)
N1—C21.323 (3)N1A—C2A1.323 (3)
N1—C91.363 (3)N1A—C9A1.363 (3)
N2—C111.354 (3)N2A—C11A1.356 (3)
N2—C81.403 (3)N2A—C8A1.410 (3)
N2—H2N0.88N2A—H2NA0.88
N3—C141.469 (3)N3A—C14A1.462 (3)
C2—C31.399 (3)C2A—C3A1.408 (4)
C2—H20.95C2A—H2A0.95
C3—C41.365 (3)C3A—C4A1.358 (4)
C3—H30.95C3A—H3A0.95
C4—C101.414 (3)C4A—C10A1.415 (3)
C4—H40.95C4A—H4A0.95
C5—C61.366 (3)C5A—C6A1.362 (3)
C5—C101.413 (3)C5A—C10A1.412 (3)
C5—H50.95C5A—H5A0.95
C6—C71.409 (3)C6A—C7A1.416 (3)
C6—H60.95C6A—H6A0.95
C7—C81.375 (3)C7A—C8A1.361 (3)
C7—H70.95C7A—H7A0.95
C8—C91.432 (3)C8A—C9A1.429 (3)
C9—C101.416 (3)C9A—C10A1.411 (3)
C11—C121.504 (3)C11A—C12A1.495 (3)
C12—C131.387 (3)C12A—C13A1.391 (3)
C12—C171.392 (3)C12A—C17A1.393 (3)
C13—C141.378 (3)C13A—C14A1.373 (3)
C13—H130.95C13A—H13A0.95
C14—C151.380 (3)C14A—C15A1.383 (3)
C15—C161.385 (3)C15A—C16A1.383 (3)
C15—H150.95C15A—H15A0.95
C16—C171.385 (3)C16A—C17A1.391 (3)
C16—H160.95C16A—H16A0.95
C17—H170.95C17A—H17A0.95
C2—N1—C9117.2 (2)C2A—N1A—C9A117.5 (2)
C11—N2—C8128.63 (19)C11A—N2A—C8A127.67 (18)
C11—N2—H2N115.7C11A—N2A—H2NA116.2
C8—N2—H2N115.7C8A—N2A—H2NA116.2
O3—N3—O2123.2 (2)O3A—N3A—O2A122.6 (2)
O3—N3—C14118.80 (19)O3A—N3A—C14A118.3 (2)
O2—N3—C14118.03 (19)O2A—N3A—C14A119.05 (19)
N1—C2—C3123.9 (2)N1A—C2A—C3A123.3 (2)
N1—C2—H2118.1N1A—C2A—H2A118.3
C3—C2—H2118.1C3A—C2A—H2A118.3
C4—C3—C2119.2 (2)C4A—C3A—C2A119.2 (2)
C4—C3—H3120.4C4A—C3A—H3A120.4
C2—C3—H3120.4C2A—C3A—H3A120.4
C3—C4—C10119.6 (2)C3A—C4A—C10A119.8 (2)
C3—C4—H4120.2C3A—C4A—H4A120.1
C10—C4—H4120.2C10A—C4A—H4A120.1
C6—C5—C10119.8 (2)C6A—C5A—C10A120.3 (2)
C6—C5—H5120.1C6A—C5A—H5A119.9
C10—C5—H5120.1C10A—C5A—H5A119.9
C5—C6—C7122.0 (2)C5A—C6A—C7A121.2 (2)
C5—C6—H6119.0C5A—C6A—H6A119.4
C7—C6—H6119.0C7A—C6A—H6A119.4
C8—C7—C6119.6 (2)C8A—C7A—C6A119.8 (2)
C8—C7—H7120.2C8A—C7A—H7A120.1
C6—C7—H7120.2C6A—C7A—H7A120.1
C7—C8—N2125.8 (2)C7A—C8A—N2A125.6 (2)
C7—C8—C9119.8 (2)C7A—C8A—C9A120.2 (2)
N2—C8—C9114.33 (19)N2A—C8A—C9A114.17 (18)
N1—C9—C10123.4 (2)N1A—C9A—C10A123.4 (2)
N1—C9—C8116.94 (19)N1A—C9A—C8A117.2 (2)
C10—C9—C8119.6 (2)C10A—C9A—C8A119.3 (2)
C5—C10—C4124.2 (2)C9A—C10A—C5A119.1 (2)
C5—C10—C9119.1 (2)C9A—C10A—C4A116.7 (2)
C4—C10—C9116.7 (2)C5A—C10A—C4A124.3 (2)
O1—C11—N2124.8 (2)O1A—C11A—N2A123.7 (2)
O1—C11—C12121.5 (2)O1A—C11A—C12A121.4 (2)
N2—C11—C12113.66 (19)N2A—C11A—C12A114.84 (19)
C13—C12—C17119.5 (2)C13A—C12A—C17A119.3 (2)
C13—C12—C11118.46 (19)C13A—C12A—C11A117.4 (2)
C17—C12—C11122.01 (19)C17A—C12A—C11A123.4 (2)
C14—C13—C12118.5 (2)C14A—C13A—C12A118.6 (2)
C14—C13—H13120.8C14A—C13A—H13A120.7
C12—C13—H13120.8C12A—C13A—H13A120.7
C15—C14—C13123.1 (2)C13A—C14A—C15A123.2 (2)
C15—C14—N3118.4 (2)C13A—C14A—N3A118.3 (2)
C13—C14—N3118.4 (2)C15A—C14A—N3A118.6 (2)
C14—C15—C16117.8 (2)C14A—C15A—C16A118.2 (2)
C14—C15—H15121.1C14A—C15A—H15A120.9
C16—C15—H15121.1C16A—C15A—H15A120.9
C17—C16—C15120.4 (2)C15A—C16A—C17A119.9 (2)
C17—C16—H16119.8C15A—C16A—H16A120.1
C15—C16—H16119.8C17A—C16A—H16A120.1
C16—C17—C12120.6 (2)C16A—C17A—C12A120.9 (2)
C16—C17—H17119.7C16A—C17A—H17A119.5
C12—C17—H17119.7C12A—C17A—H17A119.5
C9—N1—C2—C30.7 (3)C9A—N1A—C2A—C3A0.5 (3)
N1—C2—C3—C4−1.3 (4)N1A—C2A—C3A—C4A0.7 (4)
C2—C3—C4—C100.8 (3)C2A—C3A—C4A—C10A−1.4 (4)
C10—C5—C6—C70.8 (4)C10A—C5A—C6A—C7A−0.4 (4)
C5—C6—C7—C8−0.6 (4)C5A—C6A—C7A—C8A−0.3 (4)
C6—C7—C8—N2−179.1 (2)C6A—C7A—C8A—N2A−178.4 (2)
C6—C7—C8—C9−0.5 (3)C6A—C7A—C8A—C9A0.7 (3)
C11—N2—C8—C7−17.4 (4)C11A—N2A—C8A—C7A−22.8 (4)
C11—N2—C8—C9164.0 (2)C11A—N2A—C8A—C9A158.1 (2)
C2—N1—C9—C100.4 (3)C2A—N1A—C9A—C10A−1.0 (3)
C2—N1—C9—C8−179.2 (2)C2A—N1A—C9A—C8A180.0 (2)
C7—C8—C9—N1−178.9 (2)C7A—C8A—C9A—N1A178.7 (2)
N2—C8—C9—N1−0.2 (3)N2A—C8A—C9A—N1A−2.1 (3)
C7—C8—C9—C101.5 (3)C7A—C8A—C9A—C10A−0.4 (3)
N2—C8—C9—C10−179.8 (2)N2A—C8A—C9A—C10A178.8 (2)
C6—C5—C10—C4−179.9 (2)N1A—C9A—C10A—C5A−179.3 (2)
C6—C5—C10—C90.2 (3)C8A—C9A—C10A—C5A−0.3 (3)
C3—C4—C10—C5−179.7 (2)N1A—C9A—C10A—C4A0.3 (3)
C3—C4—C10—C90.2 (3)C8A—C9A—C10A—C4A179.3 (2)
N1—C9—C10—C5179.1 (2)C6A—C5A—C10A—C9A0.7 (3)
C8—C9—C10—C5−1.4 (3)C6A—C5A—C10A—C4A−178.9 (2)
N1—C9—C10—C4−0.8 (3)C3A—C4A—C10A—C9A1.0 (3)
C8—C9—C10—C4178.7 (2)C3A—C4A—C10A—C5A−179.5 (2)
C8—N2—C11—O1−3.3 (4)C8A—N2A—C11A—O1A2.6 (4)
C8—N2—C11—C12177.7 (2)C8A—N2A—C11A—C12A−176.5 (2)
O1—C11—C12—C13−31.9 (3)O1A—C11A—C12A—C13A−27.5 (3)
N2—C11—C12—C13147.2 (2)N2A—C11A—C12A—C13A151.7 (2)
O1—C11—C12—C17147.3 (2)O1A—C11A—C12A—C17A152.8 (2)
N2—C11—C12—C17−33.6 (3)N2A—C11A—C12A—C17A−28.0 (3)
C17—C12—C13—C141.5 (3)C17A—C12A—C13A—C14A0.7 (3)
C11—C12—C13—C14−179.2 (2)C11A—C12A—C13A—C14A−179.0 (2)
C12—C13—C14—C15−1.1 (3)C12A—C13A—C14A—C15A−1.8 (3)
C12—C13—C14—N3178.03 (19)C12A—C13A—C14A—N3A177.4 (2)
O3—N3—C14—C15−1.3 (3)O3A—N3A—C14A—C13A179.9 (2)
O2—N3—C14—C15178.9 (2)O2A—N3A—C14A—C13A−0.8 (3)
O3—N3—C14—C13179.5 (2)O3A—N3A—C14A—C15A−0.9 (3)
O2—N3—C14—C13−0.2 (3)O2A—N3A—C14A—C15A178.4 (2)
C13—C14—C15—C16−0.4 (3)C13A—C14A—C15A—C16A1.2 (4)
N3—C14—C15—C16−179.57 (19)N3A—C14A—C15A—C16A−178.0 (2)
C14—C15—C16—C171.6 (3)C14A—C15A—C16A—C17A0.4 (3)
C15—C16—C17—C12−1.2 (3)C15A—C16A—C17A—C12A−1.4 (3)
C13—C12—C17—C16−0.4 (3)C13A—C12A—C17A—C16A0.8 (3)
C11—C12—C17—C16−179.7 (2)C11A—C12A—C17A—C16A−179.5 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C2—H2···O2i0.952.563.395 (3)147
C2A—H2A···O2i0.952.503.346 (3)148
C4—H4···O2Ai0.952.483.317 (3)146
C16—H16···O3Aii0.952.463.147 (3)130
C16A—H16A···O1iii0.952.503.198 (3)130
C17—H17···O1Aiv0.952.453.396 (3)172

Symmetry codes: (i) x+1, y, z+1; (ii) −x+1, y+1/2, −z+1; (iii) x+1, y, z; (iv) x, y, z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2717).

References

  • Lei, G., Jing, L.-H. & Zhou, L. (2008). Acta Cryst. E64, o2392. [PMC free article] [PubMed]
  • Oku, T., Kawai, Y., Satoh, S., Yamazaki, H., Kayakiri, N., Urano, Y., Yoshihara, K. & Yoshida, N. (1999). US Patent 6008230.
  • Oku, T., Sato, S., Inoue, T., Urano, Y., Yoshimitsu, T. & Yoshida, N. (1998). Jpn Patent 10 291 988.
  • Rigaku (2004). RAPID-AUTO Rigaku/MSC Inc., The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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