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Acta Cryst. (2009). E65, o1488    [ doi:10.1107/S1600536809020728 ]

2-Nitro-N-propylbenzamide

L.-H. Guo, H.-J. Tan, J.-K. Wang and J.-T. Wang

Abstract top

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...[pi] interactions.

Comment top

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).

Related literature top

The title compound is a medicament for treating and preventing pains, see: Goodman & Serafini (2004). For bond-length data, see: Allen et al. (1987). Cg2 is the centroid of the C15–C20 ring.

Experimental top

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 top

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).

Computing details top

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

Figures top
[Figure 1] 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.
[Figure 2] Fig. 2. A packing diagram for (I).
2-nitro-N-propylbenzamide top
Crystal data top
C10H12N2O3F(000) = 1320
Mr = 208.22Dx = 1.245 Mg m−3
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 mm−1
β = 108.35 (3)°T = 298 K
V = 3333.6 (12) Å3Needle, colourless
Z = 120.30 × 0.20 × 0.10 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer		2855 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 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)] = 0.079Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.188H-atom parameters constrained
S = 1.00 w = 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 Å−3
0 restraintsΔρmin = −0.56 e Å−3
Crystal data top
C10H12N2O3V = 3333.6 (12) Å3
Mr = 208.22Z = 12
Monoclinic, P21/cMo Kα radiation
a = 15.835 (3) ŵ = 0.09 mm−1
b = 9.3910 (19) ÅT = 298 K
c = 23.618 (5) Å0.30 × 0.20 × 0.10 mm
β = 108.35 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer		2855 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)		Rint = 0.060
Tmin = 0.973, Tmax = 0.991θmax = 25.3°
6289 measured reflections3 standard reflections every 200 reflections
6056 independent reflections intensity decay: 1%
Refinement top
R[F2 > 2σ(F2)] = 0.079H-atom parameters constrained
wR(F2) = 0.188Δρmax = 0.29 e Å−3
S = 1.00Δρmin = −0.56 e Å−3
6056 reflectionsAbsolute structure: ?
388 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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) top
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) top
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, °) top
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, °) top
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.
Table 1
Hydrogen-bond geometry (Å, °) top
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.
Acknowledgements top

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

references
References top

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