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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): o1488.
Published online 2009 June 6. doi:  10.1107/S1600536809020728
PMCID: PMC2969221

2-Nitro-N-propyl­benzamide

Abstract

The title compound, C10H12N2O3, contains three mol­ecules in the asymmetric unit. In the crystal structure, inter­molecular N—H(...)O inter­actions link the mol­ecules into chains along the b axis. The crystal structure is consolidated by weak C—H(...)π inter­actions.

Related literature

The title compound is an agent for treating and preventing pains, see: Goodman & Serafini (2004 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

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Object name is e-65-o1488-scheme1.jpg

Experimental

Crystal data

  • C10H12N2O3
  • M r = 208.22
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1488-efi1.jpg
  • a = 15.835 (3) Å
  • b = 9.3910 (19) Å
  • c = 23.618 (5) Å
  • β = 108.35 (3)°
  • V = 3333.6 (12) Å3
  • Z = 12
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 298 K
  • 0.30 × 0.20 × 0.10 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.973, T max = 0.991
  • 6289 measured reflections
  • 6056 independent reflections
  • 2855 reflections with I > 2σ(I)
  • R int = 0.060
  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.079
  • wR(F 2) = 0.188
  • S = 1.00
  • 6056 reflections
  • 388 parameters
  • H-atom parameters constrained
  • Δρmax = 0.29 e Å−3
  • Δρmin = −0.56 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1985 [triangle]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, Il. DOI: 10.1107/S1600536809020728/at2796sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020728/at2796Isup2.hkl

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

Acknowledgments

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

supplementary crystallographic information

Comment

The title compound is a kind of medicament for treating and preventing pains, and traumatic injuries such as traumatic brain injury and acute spinal cord injury (Goodman & Serafini, 2004). We herein report the crystal structure of the title compound (I).

In the molecule of (I), (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. The title compound crystallized in the monolinic space group P21/c, with three independent molecules (A, B and C) in the asymmetric unit.

In the crystal structure, intermolecular N—H···O interactions (Table 1) link the molecules into chains along the b axis (Fig. 2), in which they may be effective in the stabilization of the structure. The crystal structure is consolidated by C—H···π hydrogen-bonding interactions (Table 1).

Experimental

2-Nitro-N-propylbenzamide were dissolved in DMF (50 mL). The solution was then poured to ice water. The crystalline product was isolated by filtration, washed with water (600 ml), dried and give the product 1.8 g. The crystals of (I) were obtained by evaporating the acetone slowly at room temperature for about 14 d.

Refinement

H atoms were positioned geometrically, with N—H = 0.86 and C—H = 0.93-0.97 Å, and constrained to ride on their parent atoms, with Uiso(H) = 1.2 or 1.5Ueq(C,N).

Figures

Fig. 1.
The one molecule of the three independent molecules in asymmetric unit, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
A packing diagram for (I).

Crystal data

C10H12N2O3F(000) = 1320
Mr = 208.22Dx = 1.245 Mg m3
Monoclinic, P21/cMelting point: 340 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 15.835 (3) ÅCell parameters from 25 reflections
b = 9.3910 (19) Åθ = 9–12°
c = 23.618 (5) ŵ = 0.09 mm1
β = 108.35 (3)°T = 298 K
V = 3333.6 (12) Å3Needle, colourless
Z = 120.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer2855 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.060
graphiteθmax = 25.3°, θmin = 1.4°
ω/2θ scansh = 0→19
Absorption correction: ψ scan (North et al., 1968)k = 0→11
Tmin = 0.973, Tmax = 0.991l = −28→26
6289 measured reflections3 standard reflections every 200 reflections
6056 independent reflections intensity decay: 1%

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.079Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.188H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.050P)2 + 3.P] where P = (Fo2 + 2Fc2)/3
6056 reflections(Δ/σ)max < 0.001
388 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = −0.56 e Å3

Special details

Experimental. 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 > 2sigma(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.
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
O10.2163 (2)0.1794 (3)−0.09514 (14)0.0812 (10)
O20.3600 (3)0.6643 (4)−0.09104 (16)0.1093 (13)
O30.3303 (2)0.4769 (4)−0.04864 (14)0.0799 (9)
N10.1426 (2)0.3839 (4)−0.09106 (15)0.0645 (10)
H1A0.13000.4680−0.10570.077*
N20.3298 (2)0.5438 (4)−0.09270 (19)0.0652 (10)
C10.1136 (4)0.3372 (6)0.0604 (2)0.111
H1B0.15180.37040.09820.167*
H1C0.10980.23520.06110.167*
H1D0.05530.37730.05280.167*
C20.1514 (5)0.3823 (7)0.0116 (3)0.126 (2)
H2A0.15430.48550.01130.151*
H2B0.21190.34700.02160.151*
C30.1044 (4)0.3362 (6)−0.0463 (2)0.0873 (16)
H3A0.04370.3706−0.05670.105*
H3B0.10240.2330−0.04670.105*
C40.1965 (3)0.3030 (4)−0.11057 (18)0.0605 (11)
C50.2291 (3)0.3690 (4)−0.15806 (17)0.0522 (10)
C60.1972 (3)0.3081 (5)−0.2145 (2)0.0753 (13)
H6A0.15830.2313−0.22070.090*
C70.2226 (4)0.3604 (6)−0.2617 (2)0.0874 (16)
H7A0.20080.3191−0.29930.105*
C80.2800 (3)0.4730 (6)−0.2526 (2)0.0814 (14)
H8A0.29680.5083−0.28420.098*
C90.3126 (3)0.5336 (5)−0.1981 (2)0.0650 (12)
H9A0.35160.6103−0.19230.078*
C100.2881 (3)0.4819 (4)−0.15181 (17)0.0507 (10)
O40.1360 (2)−0.3230 (3)−0.12406 (13)0.0808 (10)
O5−0.0495 (3)0.1095 (5)−0.1661 (2)0.1416 (18)
O6−0.0153 (2)−0.0953 (5)−0.12712 (17)0.1127 (14)
N30.1889 (2)−0.1148 (3)−0.07927 (14)0.0598 (9)
H3C0.1982−0.0265−0.08500.072*
N4−0.0107 (3)−0.0024 (5)−0.16209 (18)0.0771 (11)
C110.1902 (4)−0.1746 (6)0.0794 (2)0.115
H11A0.1509−0.13810.09970.173*
H11B0.2500−0.14500.10010.173*
H11C0.1873−0.27670.07850.173*
C120.1632 (4)−0.1196 (6)0.0183 (2)0.106
H12A0.1651−0.01640.01980.127*
H12B0.1020−0.1475−0.00170.127*
C130.2203 (3)−0.1708 (4)−0.01861 (18)0.0720 (13)
H13A0.2813−0.14090.00030.086*
H13B0.2193−0.2741−0.02000.086*
C140.1471 (3)−0.1932 (4)−0.12538 (18)0.0560 (11)
C150.1150 (3)−0.1159 (4)−0.18493 (18)0.0531 (10)
C160.1612 (3)−0.1351 (5)−0.2252 (2)0.0692 (12)
H16A0.2118−0.1919−0.21480.083*
C170.1330 (3)−0.0707 (5)−0.2807 (2)0.0776 (14)
H17A0.1650−0.0847−0.30720.093*
C180.0584 (3)0.0135 (5)−0.29718 (19)0.0671 (12)
H18A0.03920.0549−0.33480.081*
C190.0128 (3)0.0357 (4)−0.25787 (18)0.0597 (11)
H19A−0.03740.0936−0.26820.072*
C200.0415 (3)−0.0284 (4)−0.20266 (17)0.0517 (10)
O70.4897 (2)0.9114 (3)0.26431 (12)0.0691 (9)
O80.3181 (3)0.5045 (5)0.14397 (19)0.1227 (15)
O90.3425 (2)0.6663 (4)0.21211 (18)0.0980 (12)
N50.5255 (2)0.6835 (3)0.29072 (13)0.0589 (9)
H5A0.53870.60180.27930.071*
N60.3587 (3)0.6078 (5)0.1705 (2)0.0788 (11)
C210.5982 (4)0.6457 (6)0.45860 (19)0.111 (2)
H21A0.64820.59780.48580.167*
H21B0.54400.60410.46100.167*
H21C0.59990.74480.46890.167*
C220.6022 (4)0.6307 (6)0.3953 (2)0.0946 (17)
H22A0.65770.67040.39330.114*
H22B0.60100.53050.38510.114*
C230.5289 (3)0.7021 (5)0.35266 (18)0.0764 (14)
H23A0.53270.80300.36180.092*
H23B0.47380.66700.35720.092*
C240.5028 (3)0.7884 (4)0.25144 (18)0.0520 (10)
C250.4954 (3)0.7494 (4)0.18769 (16)0.0472 (9)
C260.4311 (3)0.6667 (4)0.15025 (18)0.0594 (11)
C270.4272 (4)0.6379 (5)0.0922 (2)0.0803 (15)
H27A0.38310.57910.06820.096*
C280.4895 (4)0.6978 (7)0.0712 (2)0.0895 (17)
H28A0.48720.68160.03190.107*
C290.5551 (4)0.7811 (6)0.1067 (2)0.0786 (15)
H29A0.59780.82030.09190.094*
C300.5581 (3)0.8073 (4)0.16499 (19)0.0632 (12)
H30A0.60290.86470.18920.076*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.122 (3)0.0300 (15)0.095 (2)−0.0039 (17)0.039 (2)0.0083 (15)
O20.139 (3)0.084 (3)0.121 (3)−0.061 (2)0.064 (3)−0.040 (2)
O30.094 (2)0.079 (2)0.061 (2)−0.0115 (19)0.0156 (18)−0.0069 (18)
N10.085 (3)0.046 (2)0.073 (2)−0.0003 (19)0.039 (2)0.0162 (18)
N20.068 (2)0.051 (2)0.084 (3)−0.011 (2)0.034 (2)−0.016 (2)
C10.1110.1110.1110.0000.0350.000
C20.193 (7)0.117 (5)0.093 (4)−0.035 (5)0.080 (5)0.006 (4)
C30.108 (4)0.083 (4)0.082 (4)−0.011 (3)0.047 (3)0.014 (3)
C40.082 (3)0.036 (2)0.062 (3)−0.008 (2)0.021 (2)0.003 (2)
C50.063 (3)0.038 (2)0.056 (2)0.002 (2)0.021 (2)−0.001 (2)
C60.086 (3)0.065 (3)0.071 (3)−0.015 (3)0.020 (3)−0.014 (3)
C70.092 (4)0.111 (4)0.056 (3)−0.005 (4)0.019 (3)−0.021 (3)
C80.087 (4)0.099 (4)0.069 (3)0.005 (3)0.039 (3)0.009 (3)
C90.068 (3)0.057 (3)0.080 (3)−0.003 (2)0.036 (3)0.006 (2)
C100.055 (2)0.043 (2)0.058 (3)−0.001 (2)0.023 (2)−0.005 (2)
O40.110 (3)0.0349 (16)0.082 (2)−0.0110 (17)0.0087 (19)0.0087 (15)
O50.171 (4)0.142 (4)0.147 (4)0.089 (4)0.100 (3)0.042 (3)
O60.099 (3)0.145 (4)0.116 (3)0.027 (3)0.064 (2)0.058 (3)
N30.081 (3)0.0338 (17)0.059 (2)−0.0053 (18)0.0145 (19)0.0063 (17)
N40.069 (3)0.088 (3)0.077 (3)0.015 (2)0.028 (2)0.016 (3)
C110.1150.1150.1150.0000.0360.000
C120.1050.1050.1050.0000.0320.000
C130.098 (4)0.050 (3)0.065 (3)−0.003 (3)0.021 (3)0.004 (2)
C140.065 (3)0.037 (2)0.063 (3)−0.002 (2)0.016 (2)0.006 (2)
C150.057 (3)0.034 (2)0.067 (3)0.000 (2)0.019 (2)0.000 (2)
C160.069 (3)0.061 (3)0.081 (3)0.017 (2)0.028 (3)0.000 (3)
C170.089 (4)0.084 (3)0.073 (3)0.001 (3)0.045 (3)−0.004 (3)
C180.075 (3)0.072 (3)0.054 (3)−0.007 (3)0.019 (2)0.006 (2)
C190.055 (3)0.058 (3)0.061 (3)0.002 (2)0.012 (2)0.014 (2)
C200.057 (3)0.044 (2)0.058 (3)−0.006 (2)0.023 (2)0.002 (2)
O70.107 (2)0.0359 (15)0.073 (2)0.0053 (16)0.0406 (18)−0.0046 (14)
O80.108 (3)0.116 (3)0.138 (4)−0.048 (3)0.029 (3)−0.039 (3)
O90.083 (2)0.111 (3)0.114 (3)−0.024 (2)0.052 (2)−0.029 (2)
N50.099 (3)0.0348 (17)0.050 (2)0.0123 (18)0.0333 (19)0.0000 (16)
N60.069 (3)0.075 (3)0.088 (3)−0.003 (2)0.018 (2)−0.007 (2)
C210.165 (6)0.107 (4)0.051 (3)0.029 (4)0.018 (3)−0.005 (3)
C220.114 (4)0.094 (4)0.062 (3)0.027 (3)0.007 (3)−0.010 (3)
C230.119 (4)0.055 (3)0.060 (3)0.018 (3)0.035 (3)0.001 (2)
C240.060 (2)0.044 (2)0.056 (2)−0.003 (2)0.024 (2)0.000 (2)
C250.057 (3)0.039 (2)0.050 (2)0.012 (2)0.022 (2)0.0051 (19)
C260.062 (3)0.059 (3)0.055 (3)0.006 (2)0.017 (2)0.000 (2)
C270.094 (4)0.084 (4)0.058 (3)0.019 (3)0.016 (3)−0.008 (3)
C280.099 (4)0.111 (5)0.060 (3)0.033 (4)0.026 (3)0.009 (3)
C290.086 (4)0.088 (4)0.076 (3)0.031 (3)0.046 (3)0.034 (3)
C300.074 (3)0.053 (3)0.068 (3)0.007 (2)0.030 (2)0.013 (2)

Geometric parameters (Å, °)

O1—C41.228 (4)C13—H13A0.9700
O2—N21.223 (4)C13—H13B0.9700
O3—N21.214 (4)C14—C151.521 (5)
N1—C41.328 (5)C15—C201.377 (5)
N1—C31.444 (5)C15—C161.382 (5)
N1—H1A0.8600C16—C171.384 (6)
N2—C101.464 (5)C16—H16A0.9300
C1—C21.518 (7)C17—C181.372 (6)
C1—H1B0.9600C17—H17A0.9300
C1—H1C0.9600C18—C191.360 (5)
C1—H1D0.9600C18—H18A0.9300
C2—C31.404 (7)C19—C201.377 (5)
C2—H2A0.9700C19—H19A0.9300
C2—H2B0.9700O7—C241.228 (4)
C3—H3A0.9700O8—N61.222 (5)
C3—H3B0.9700O9—N61.221 (5)
C4—C51.508 (5)N5—C241.324 (5)
C5—C101.391 (5)N5—C231.458 (5)
C5—C61.391 (5)N5—H5A0.8600
C6—C71.389 (6)N6—C261.482 (6)
C6—H6A0.9300C21—C221.524 (6)
C7—C81.365 (7)C21—H21A0.9600
C7—H7A0.9300C21—H21B0.9600
C8—C91.352 (6)C21—H21C0.9600
C8—H8A0.9300C22—C231.440 (6)
C9—C101.359 (5)C22—H22A0.9700
C9—H9A0.9300C22—H22B0.9700
O4—C141.234 (4)C23—H23A0.9700
O5—N41.206 (5)C23—H23B0.9700
O6—N41.219 (5)C24—C251.518 (5)
N3—C141.309 (5)C25—C261.362 (5)
N3—C131.459 (5)C25—C301.380 (5)
N3—H3C0.8600C26—C271.379 (6)
N4—C201.470 (5)C27—C281.358 (7)
C11—C121.464 (7)C27—H27A0.9300
C11—H11A0.9600C28—C291.358 (7)
C11—H11B0.9600C28—H28A0.9300
C11—H11C0.9600C29—C301.385 (6)
C12—C131.518 (6)C29—H29A0.9300
C12—H12A0.9700C30—H30A0.9300
C12—H12B0.9700
C4—N1—C3122.6 (4)H13A—C13—H13B108.0
C4—N1—H1A118.7O4—C14—N3125.0 (4)
C3—N1—H1A118.7O4—C14—C15119.1 (4)
O3—N2—O2123.7 (4)N3—C14—C15115.8 (3)
O3—N2—C10119.4 (4)C20—C15—C16116.6 (4)
O2—N2—C10116.9 (4)C20—C15—C14124.8 (4)
C2—C1—H1B109.5C16—C15—C14118.6 (4)
C2—C1—H1C109.5C15—C16—C17120.8 (4)
H1B—C1—H1C109.5C15—C16—H16A119.6
C2—C1—H1D109.5C17—C16—H16A119.6
H1B—C1—H1D109.5C18—C17—C16120.8 (4)
H1C—C1—H1D109.5C18—C17—H17A119.6
C3—C2—C1116.0 (5)C16—C17—H17A119.6
C3—C2—H2A108.3C19—C18—C17119.3 (4)
C1—C2—H2A108.3C19—C18—H18A120.4
C3—C2—H2B108.3C17—C18—H18A120.4
C1—C2—H2B108.3C18—C19—C20119.5 (4)
H2A—C2—H2B107.4C18—C19—H19A120.3
C2—C3—N1113.6 (4)C20—C19—H19A120.3
C2—C3—H3A108.8C19—C20—C15123.0 (4)
N1—C3—H3A108.8C19—C20—N4117.3 (4)
C2—C3—H3B108.8C15—C20—N4119.7 (4)
N1—C3—H3B108.8C24—N5—C23122.0 (3)
H3A—C3—H3B107.7C24—N5—H5A119.0
O1—C4—N1124.7 (4)C23—N5—H5A119.0
O1—C4—C5119.6 (4)O9—N6—O8124.1 (5)
N1—C4—C5115.5 (3)O9—N6—C26118.1 (4)
C10—C5—C6116.4 (4)O8—N6—C26117.8 (5)
C10—C5—C4127.6 (4)C22—C21—H21A109.5
C6—C5—C4116.0 (4)C22—C21—H21B109.5
C7—C6—C5120.9 (4)H21A—C21—H21B109.5
C7—C6—H6A119.5C22—C21—H21C109.5
C5—C6—H6A119.5H21A—C21—H21C109.5
C8—C7—C6119.6 (5)H21B—C21—H21C109.5
C8—C7—H7A120.2C23—C22—C21111.7 (4)
C6—C7—H7A120.2C23—C22—H22A109.3
C9—C8—C7120.8 (5)C21—C22—H22A109.3
C9—C8—H8A119.6C23—C22—H22B109.3
C7—C8—H8A119.6C21—C22—H22B109.3
C8—C9—C10119.6 (4)H22A—C22—H22B107.9
C8—C9—H9A120.2C22—C23—N5114.4 (4)
C10—C9—H9A120.2C22—C23—H23A108.7
C9—C10—C5122.6 (4)N5—C23—H23A108.7
C9—C10—N2117.9 (4)C22—C23—H23B108.7
C5—C10—N2119.4 (4)N5—C23—H23B108.7
C14—N3—C13122.8 (3)H23A—C23—H23B107.6
C14—N3—H3C118.6O7—C24—N5123.8 (4)
C13—N3—H3C118.6O7—C24—C25120.4 (4)
O5—N4—O6122.6 (5)N5—C24—C25115.7 (3)
O5—N4—C20118.1 (4)C26—C25—C30117.0 (4)
O6—N4—C20119.3 (4)C26—C25—C24126.2 (4)
C12—C11—H11A109.5C30—C25—C24116.7 (4)
C12—C11—H11B109.5C25—C26—C27123.2 (4)
H11A—C11—H11B109.5C25—C26—N6119.9 (4)
C12—C11—H11C109.5C27—C26—N6116.8 (4)
H11A—C11—H11C109.5C28—C27—C26118.1 (5)
H11B—C11—H11C109.5C28—C27—H27A121.0
C11—C12—C13114.4 (5)C26—C27—H27A121.0
C11—C12—H12A108.7C27—C28—C29121.1 (5)
C13—C12—H12A108.7C27—C28—H28A119.5
C11—C12—H12B108.7C29—C28—H28A119.5
C13—C12—H12B108.7C28—C29—C30119.7 (5)
H12A—C12—H12B107.6C28—C29—H29A120.1
N3—C13—C12111.7 (4)C30—C29—H29A120.1
N3—C13—H13A109.3C25—C30—C29120.8 (4)
C12—C13—H13A109.3C25—C30—H30A119.6
N3—C13—H13B109.3C29—C30—H30A119.6
C12—C13—H13B109.3
C1—C2—C3—N1179.2 (5)C17—C18—C19—C20−1.0 (6)
C4—N1—C3—C297.2 (6)C18—C19—C20—C15−0.3 (6)
C3—N1—C4—O13.3 (7)C18—C19—C20—N4−179.3 (4)
C3—N1—C4—C5179.1 (4)C16—C15—C20—C191.3 (6)
O1—C4—C5—C10−114.7 (5)C14—C15—C20—C19−177.6 (4)
N1—C4—C5—C1069.3 (6)C16—C15—C20—N4−179.7 (4)
O1—C4—C5—C664.3 (6)C14—C15—C20—N41.3 (6)
N1—C4—C5—C6−111.7 (4)O5—N4—C20—C19−29.9 (6)
C10—C5—C6—C7−1.0 (6)O6—N4—C20—C19148.1 (4)
C4—C5—C6—C7179.9 (4)O5—N4—C20—C15151.1 (5)
C5—C6—C7—C80.2 (8)O6—N4—C20—C15−31.0 (6)
C6—C7—C8—C90.3 (8)C21—C22—C23—N5−176.0 (4)
C7—C8—C9—C100.1 (7)C24—N5—C23—C22−141.0 (5)
C8—C9—C10—C5−0.9 (7)C23—N5—C24—O76.1 (7)
C8—C9—C10—N2175.7 (4)C23—N5—C24—C25−175.4 (4)
C6—C5—C10—C91.4 (6)O7—C24—C25—C26−110.9 (5)
C4—C5—C10—C9−179.6 (4)N5—C24—C25—C2670.5 (5)
C6—C5—C10—N2−175.2 (4)O7—C24—C25—C3066.7 (5)
C4—C5—C10—N23.9 (6)N5—C24—C25—C30−111.9 (4)
O3—N2—C10—C9−158.9 (4)C30—C25—C26—C270.9 (6)
O2—N2—C10—C923.5 (6)C24—C25—C26—C27178.5 (4)
O3—N2—C10—C517.8 (6)C30—C25—C26—N6−176.6 (4)
O2—N2—C10—C5−159.8 (4)C24—C25—C26—N61.1 (6)
C14—N3—C13—C12−106.3 (5)O9—N6—C26—C2521.4 (6)
C11—C12—C13—N3178.8 (4)O8—N6—C26—C25−159.5 (4)
C13—N3—C14—O4−6.3 (7)O9—N6—C26—C27−156.2 (4)
C13—N3—C14—C15177.1 (4)O8—N6—C26—C2722.9 (6)
O4—C14—C15—C20106.6 (5)C25—C26—C27—C28−1.5 (7)
N3—C14—C15—C20−76.5 (5)N6—C26—C27—C28176.0 (4)
O4—C14—C15—C16−72.3 (5)C26—C27—C28—C291.5 (8)
N3—C14—C15—C16104.6 (5)C27—C28—C29—C30−0.9 (8)
C20—C15—C16—C17−1.1 (6)C26—C25—C30—C29−0.2 (6)
C14—C15—C16—C17177.9 (4)C24—C25—C30—C29−178.1 (4)
C15—C16—C17—C18−0.1 (7)C28—C29—C30—C250.2 (7)
C16—C17—C18—C191.2 (7)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O4i0.862.022.854 (5)163
N3—H3C···O10.861.982.840 (4)177
N5—H5A···O7ii0.862.042.843 (4)154
C6—H6A···Cg20.932.863.751 (5)162

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2796).

References

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  • Goodman, C. R. & Serafini, T. (2004). Renovis, INT., San Francisco, US. CA Patent No. 2 510 042.
  • Harms, K. & Wocadlo, S. (1995). XCAD4 University of Marburg, Germany.
  • North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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