organic compounds
2-Nitro-N-propylbenzamide
aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
*Correspondence e-mail: wjk@njut.edu.cn
The title compound, C10H12N2O3, contains three molecules in the In the intermolecular N—H⋯O interactions link the molecules into chains along the b axis. The 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). For bond-length data, see: Allen et al. (1987).
Experimental
Crystal data
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Refinement
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Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell CAD-4 Software; 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.
Supporting information
10.1107/S1600536809020728/at2796sup1.cif
contains datablocks I, Il. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809020728/at2796Isup2.hkl
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.
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).
Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell
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).C10H12N2O3 | F(000) = 1320 |
Mr = 208.22 | Dx = 1.245 Mg m−3 |
Monoclinic, P21/c | Melting point: 340 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 15.835 (3) Å | Cell parameters from 25 reflections |
b = 9.3910 (19) Å | θ = 9–12° |
c = 23.618 (5) Å | µ = 0.09 mm−1 |
β = 108.35 (3)° | T = 298 K |
V = 3333.6 (12) Å3 | Needle, colourless |
Z = 12 | 0.30 × 0.20 × 0.10 mm |
Enraf–Nonius CAD-4 diffractometer | 2855 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.060 |
Graphite monochromator | θmax = 25.3°, θmin = 1.4° |
ω/2θ scans | h = 0→19 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→11 |
Tmin = 0.973, Tmax = 0.991 | l = −28→26 |
6289 measured reflections | 3 standard reflections every 200 reflections |
6056 independent reflections | intensity decay: 1% |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.079 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.188 | H-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 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.56 e Å−3 |
C10H12N2O3 | V = 3333.6 (12) Å3 |
Mr = 208.22 | Z = 12 |
Monoclinic, P21/c | Mo Kα radiation |
a = 15.835 (3) Å | µ = 0.09 mm−1 |
b = 9.3910 (19) Å | T = 298 K |
c = 23.618 (5) Å | 0.30 × 0.20 × 0.10 mm |
β = 108.35 (3)° |
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 = 0.991 | 3 standard reflections every 200 reflections |
6289 measured reflections | intensity decay: 1% |
6056 independent reflections |
R[F2 > 2σ(F2)] = 0.079 | 0 restraints |
wR(F2) = 0.188 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.29 e Å−3 |
6056 reflections | Δρmin = −0.56 e Å−3 |
388 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.2163 (2) | 0.1794 (3) | −0.09514 (14) | 0.0812 (10) | |
O2 | 0.3600 (3) | 0.6643 (4) | −0.09104 (16) | 0.1093 (13) | |
O3 | 0.3303 (2) | 0.4769 (4) | −0.04864 (14) | 0.0799 (9) | |
N1 | 0.1426 (2) | 0.3839 (4) | −0.09106 (15) | 0.0645 (10) | |
H1A | 0.1300 | 0.4680 | −0.1057 | 0.077* | |
N2 | 0.3298 (2) | 0.5438 (4) | −0.09270 (19) | 0.0652 (10) | |
C1 | 0.1136 (4) | 0.3372 (6) | 0.0604 (2) | 0.111 | |
H1B | 0.1518 | 0.3704 | 0.0982 | 0.167* | |
H1C | 0.1098 | 0.2352 | 0.0611 | 0.167* | |
H1D | 0.0553 | 0.3773 | 0.0528 | 0.167* | |
C2 | 0.1514 (5) | 0.3823 (7) | 0.0116 (3) | 0.126 (2) | |
H2A | 0.1543 | 0.4855 | 0.0113 | 0.151* | |
H2B | 0.2119 | 0.3470 | 0.0216 | 0.151* | |
C3 | 0.1044 (4) | 0.3362 (6) | −0.0463 (2) | 0.0873 (16) | |
H3A | 0.0437 | 0.3706 | −0.0567 | 0.105* | |
H3B | 0.1024 | 0.2330 | −0.0467 | 0.105* | |
C4 | 0.1965 (3) | 0.3030 (4) | −0.11057 (18) | 0.0605 (11) | |
C5 | 0.2291 (3) | 0.3690 (4) | −0.15806 (17) | 0.0522 (10) | |
C6 | 0.1972 (3) | 0.3081 (5) | −0.2145 (2) | 0.0753 (13) | |
H6A | 0.1583 | 0.2313 | −0.2207 | 0.090* | |
C7 | 0.2226 (4) | 0.3604 (6) | −0.2617 (2) | 0.0874 (16) | |
H7A | 0.2008 | 0.3191 | −0.2993 | 0.105* | |
C8 | 0.2800 (3) | 0.4730 (6) | −0.2526 (2) | 0.0814 (14) | |
H8A | 0.2968 | 0.5083 | −0.2842 | 0.098* | |
C9 | 0.3126 (3) | 0.5336 (5) | −0.1981 (2) | 0.0650 (12) | |
H9A | 0.3516 | 0.6103 | −0.1923 | 0.078* | |
C10 | 0.2881 (3) | 0.4819 (4) | −0.15181 (17) | 0.0507 (10) | |
O4 | 0.1360 (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) | |
N3 | 0.1889 (2) | −0.1148 (3) | −0.07927 (14) | 0.0598 (9) | |
H3C | 0.1982 | −0.0265 | −0.0850 | 0.072* | |
N4 | −0.0107 (3) | −0.0024 (5) | −0.16209 (18) | 0.0771 (11) | |
C11 | 0.1902 (4) | −0.1746 (6) | 0.0794 (2) | 0.115 | |
H11A | 0.1509 | −0.1381 | 0.0997 | 0.173* | |
H11B | 0.2500 | −0.1450 | 0.1001 | 0.173* | |
H11C | 0.1873 | −0.2767 | 0.0785 | 0.173* | |
C12 | 0.1632 (4) | −0.1196 (6) | 0.0183 (2) | 0.106 | |
H12A | 0.1651 | −0.0164 | 0.0198 | 0.127* | |
H12B | 0.1020 | −0.1475 | −0.0017 | 0.127* | |
C13 | 0.2203 (3) | −0.1708 (4) | −0.01861 (18) | 0.0720 (13) | |
H13A | 0.2813 | −0.1409 | 0.0003 | 0.086* | |
H13B | 0.2193 | −0.2741 | −0.0200 | 0.086* | |
C14 | 0.1471 (3) | −0.1932 (4) | −0.12538 (18) | 0.0560 (11) | |
C15 | 0.1150 (3) | −0.1159 (4) | −0.18493 (18) | 0.0531 (10) | |
C16 | 0.1612 (3) | −0.1351 (5) | −0.2252 (2) | 0.0692 (12) | |
H16A | 0.2118 | −0.1919 | −0.2148 | 0.083* | |
C17 | 0.1330 (3) | −0.0707 (5) | −0.2807 (2) | 0.0776 (14) | |
H17A | 0.1650 | −0.0847 | −0.3072 | 0.093* | |
C18 | 0.0584 (3) | 0.0135 (5) | −0.29718 (19) | 0.0671 (12) | |
H18A | 0.0392 | 0.0549 | −0.3348 | 0.081* | |
C19 | 0.0128 (3) | 0.0357 (4) | −0.25787 (18) | 0.0597 (11) | |
H19A | −0.0374 | 0.0936 | −0.2682 | 0.072* | |
C20 | 0.0415 (3) | −0.0284 (4) | −0.20266 (17) | 0.0517 (10) | |
O7 | 0.4897 (2) | 0.9114 (3) | 0.26431 (12) | 0.0691 (9) | |
O8 | 0.3181 (3) | 0.5045 (5) | 0.14397 (19) | 0.1227 (15) | |
O9 | 0.3425 (2) | 0.6663 (4) | 0.21211 (18) | 0.0980 (12) | |
N5 | 0.5255 (2) | 0.6835 (3) | 0.29072 (13) | 0.0589 (9) | |
H5A | 0.5387 | 0.6018 | 0.2793 | 0.071* | |
N6 | 0.3587 (3) | 0.6078 (5) | 0.1705 (2) | 0.0788 (11) | |
C21 | 0.5982 (4) | 0.6457 (6) | 0.45860 (19) | 0.111 (2) | |
H21A | 0.6482 | 0.5978 | 0.4858 | 0.167* | |
H21B | 0.5440 | 0.6041 | 0.4610 | 0.167* | |
H21C | 0.5999 | 0.7448 | 0.4689 | 0.167* | |
C22 | 0.6022 (4) | 0.6307 (6) | 0.3953 (2) | 0.0946 (17) | |
H22A | 0.6577 | 0.6704 | 0.3933 | 0.114* | |
H22B | 0.6010 | 0.5305 | 0.3851 | 0.114* | |
C23 | 0.5289 (3) | 0.7021 (5) | 0.35266 (18) | 0.0764 (14) | |
H23A | 0.5327 | 0.8030 | 0.3618 | 0.092* | |
H23B | 0.4738 | 0.6670 | 0.3572 | 0.092* | |
C24 | 0.5028 (3) | 0.7884 (4) | 0.25144 (18) | 0.0520 (10) | |
C25 | 0.4954 (3) | 0.7494 (4) | 0.18769 (16) | 0.0472 (9) | |
C26 | 0.4311 (3) | 0.6667 (4) | 0.15025 (18) | 0.0594 (11) | |
C27 | 0.4272 (4) | 0.6379 (5) | 0.0922 (2) | 0.0803 (15) | |
H27A | 0.3831 | 0.5791 | 0.0682 | 0.096* | |
C28 | 0.4895 (4) | 0.6978 (7) | 0.0712 (2) | 0.0895 (17) | |
H28A | 0.4872 | 0.6816 | 0.0319 | 0.107* | |
C29 | 0.5551 (4) | 0.7811 (6) | 0.1067 (2) | 0.0786 (15) | |
H29A | 0.5978 | 0.8203 | 0.0919 | 0.094* | |
C30 | 0.5581 (3) | 0.8073 (4) | 0.16499 (19) | 0.0632 (12) | |
H30A | 0.6029 | 0.8647 | 0.1892 | 0.076* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.122 (3) | 0.0300 (15) | 0.095 (2) | −0.0039 (17) | 0.039 (2) | 0.0083 (15) |
O2 | 0.139 (3) | 0.084 (3) | 0.121 (3) | −0.061 (2) | 0.064 (3) | −0.040 (2) |
O3 | 0.094 (2) | 0.079 (2) | 0.061 (2) | −0.0115 (19) | 0.0156 (18) | −0.0069 (18) |
N1 | 0.085 (3) | 0.046 (2) | 0.073 (2) | −0.0003 (19) | 0.039 (2) | 0.0162 (18) |
N2 | 0.068 (2) | 0.051 (2) | 0.084 (3) | −0.011 (2) | 0.034 (2) | −0.016 (2) |
C1 | 0.111 | 0.111 | 0.111 | 0.000 | 0.035 | 0.000 |
C2 | 0.193 (7) | 0.117 (5) | 0.093 (4) | −0.035 (5) | 0.080 (5) | 0.006 (4) |
C3 | 0.108 (4) | 0.083 (4) | 0.082 (4) | −0.011 (3) | 0.047 (3) | 0.014 (3) |
C4 | 0.082 (3) | 0.036 (2) | 0.062 (3) | −0.008 (2) | 0.021 (2) | 0.003 (2) |
C5 | 0.063 (3) | 0.038 (2) | 0.056 (2) | 0.002 (2) | 0.021 (2) | −0.001 (2) |
C6 | 0.086 (3) | 0.065 (3) | 0.071 (3) | −0.015 (3) | 0.020 (3) | −0.014 (3) |
C7 | 0.092 (4) | 0.111 (4) | 0.056 (3) | −0.005 (4) | 0.019 (3) | −0.021 (3) |
C8 | 0.087 (4) | 0.099 (4) | 0.069 (3) | 0.005 (3) | 0.039 (3) | 0.009 (3) |
C9 | 0.068 (3) | 0.057 (3) | 0.080 (3) | −0.003 (2) | 0.036 (3) | 0.006 (2) |
C10 | 0.055 (2) | 0.043 (2) | 0.058 (3) | −0.001 (2) | 0.023 (2) | −0.005 (2) |
O4 | 0.110 (3) | 0.0349 (16) | 0.082 (2) | −0.0110 (17) | 0.0087 (19) | 0.0087 (15) |
O5 | 0.171 (4) | 0.142 (4) | 0.147 (4) | 0.089 (4) | 0.100 (3) | 0.042 (3) |
O6 | 0.099 (3) | 0.145 (4) | 0.116 (3) | 0.027 (3) | 0.064 (2) | 0.058 (3) |
N3 | 0.081 (3) | 0.0338 (17) | 0.059 (2) | −0.0053 (18) | 0.0145 (19) | 0.0063 (17) |
N4 | 0.069 (3) | 0.088 (3) | 0.077 (3) | 0.015 (2) | 0.028 (2) | 0.016 (3) |
C11 | 0.115 | 0.115 | 0.115 | 0.000 | 0.036 | 0.000 |
C12 | 0.105 | 0.105 | 0.105 | 0.000 | 0.032 | 0.000 |
C13 | 0.098 (4) | 0.050 (3) | 0.065 (3) | −0.003 (3) | 0.021 (3) | 0.004 (2) |
C14 | 0.065 (3) | 0.037 (2) | 0.063 (3) | −0.002 (2) | 0.016 (2) | 0.006 (2) |
C15 | 0.057 (3) | 0.034 (2) | 0.067 (3) | 0.000 (2) | 0.019 (2) | 0.000 (2) |
C16 | 0.069 (3) | 0.061 (3) | 0.081 (3) | 0.017 (2) | 0.028 (3) | 0.000 (3) |
C17 | 0.089 (4) | 0.084 (3) | 0.073 (3) | 0.001 (3) | 0.045 (3) | −0.004 (3) |
C18 | 0.075 (3) | 0.072 (3) | 0.054 (3) | −0.007 (3) | 0.019 (2) | 0.006 (2) |
C19 | 0.055 (3) | 0.058 (3) | 0.061 (3) | 0.002 (2) | 0.012 (2) | 0.014 (2) |
C20 | 0.057 (3) | 0.044 (2) | 0.058 (3) | −0.006 (2) | 0.023 (2) | 0.002 (2) |
O7 | 0.107 (2) | 0.0359 (15) | 0.073 (2) | 0.0053 (16) | 0.0406 (18) | −0.0046 (14) |
O8 | 0.108 (3) | 0.116 (3) | 0.138 (4) | −0.048 (3) | 0.029 (3) | −0.039 (3) |
O9 | 0.083 (2) | 0.111 (3) | 0.114 (3) | −0.024 (2) | 0.052 (2) | −0.029 (2) |
N5 | 0.099 (3) | 0.0348 (17) | 0.050 (2) | 0.0123 (18) | 0.0333 (19) | 0.0000 (16) |
N6 | 0.069 (3) | 0.075 (3) | 0.088 (3) | −0.003 (2) | 0.018 (2) | −0.007 (2) |
C21 | 0.165 (6) | 0.107 (4) | 0.051 (3) | 0.029 (4) | 0.018 (3) | −0.005 (3) |
C22 | 0.114 (4) | 0.094 (4) | 0.062 (3) | 0.027 (3) | 0.007 (3) | −0.010 (3) |
C23 | 0.119 (4) | 0.055 (3) | 0.060 (3) | 0.018 (3) | 0.035 (3) | 0.001 (2) |
C24 | 0.060 (2) | 0.044 (2) | 0.056 (2) | −0.003 (2) | 0.024 (2) | 0.000 (2) |
C25 | 0.057 (3) | 0.039 (2) | 0.050 (2) | 0.012 (2) | 0.022 (2) | 0.0051 (19) |
C26 | 0.062 (3) | 0.059 (3) | 0.055 (3) | 0.006 (2) | 0.017 (2) | 0.000 (2) |
C27 | 0.094 (4) | 0.084 (4) | 0.058 (3) | 0.019 (3) | 0.016 (3) | −0.008 (3) |
C28 | 0.099 (4) | 0.111 (5) | 0.060 (3) | 0.033 (4) | 0.026 (3) | 0.009 (3) |
C29 | 0.086 (4) | 0.088 (4) | 0.076 (3) | 0.031 (3) | 0.046 (3) | 0.034 (3) |
C30 | 0.074 (3) | 0.053 (3) | 0.068 (3) | 0.007 (2) | 0.030 (2) | 0.013 (2) |
O1—C4 | 1.228 (4) | C13—H13A | 0.9700 |
O2—N2 | 1.223 (4) | C13—H13B | 0.9700 |
O3—N2 | 1.214 (4) | C14—C15 | 1.521 (5) |
N1—C4 | 1.328 (5) | C15—C20 | 1.377 (5) |
N1—C3 | 1.444 (5) | C15—C16 | 1.382 (5) |
N1—H1A | 0.8600 | C16—C17 | 1.384 (6) |
N2—C10 | 1.464 (5) | C16—H16A | 0.9300 |
C1—C2 | 1.518 (7) | C17—C18 | 1.372 (6) |
C1—H1B | 0.9600 | C17—H17A | 0.9300 |
C1—H1C | 0.9600 | C18—C19 | 1.360 (5) |
C1—H1D | 0.9600 | C18—H18A | 0.9300 |
C2—C3 | 1.404 (7) | C19—C20 | 1.377 (5) |
C2—H2A | 0.9700 | C19—H19A | 0.9300 |
C2—H2B | 0.9700 | O7—C24 | 1.228 (4) |
C3—H3A | 0.9700 | O8—N6 | 1.222 (5) |
C3—H3B | 0.9700 | O9—N6 | 1.221 (5) |
C4—C5 | 1.508 (5) | N5—C24 | 1.324 (5) |
C5—C10 | 1.391 (5) | N5—C23 | 1.458 (5) |
C5—C6 | 1.391 (5) | N5—H5A | 0.8600 |
C6—C7 | 1.389 (6) | N6—C26 | 1.482 (6) |
C6—H6A | 0.9300 | C21—C22 | 1.524 (6) |
C7—C8 | 1.365 (7) | C21—H21A | 0.9600 |
C7—H7A | 0.9300 | C21—H21B | 0.9600 |
C8—C9 | 1.352 (6) | C21—H21C | 0.9600 |
C8—H8A | 0.9300 | C22—C23 | 1.440 (6) |
C9—C10 | 1.359 (5) | C22—H22A | 0.9700 |
C9—H9A | 0.9300 | C22—H22B | 0.9700 |
O4—C14 | 1.234 (4) | C23—H23A | 0.9700 |
O5—N4 | 1.206 (5) | C23—H23B | 0.9700 |
O6—N4 | 1.219 (5) | C24—C25 | 1.518 (5) |
N3—C14 | 1.309 (5) | C25—C26 | 1.362 (5) |
N3—C13 | 1.459 (5) | C25—C30 | 1.380 (5) |
N3—H3C | 0.8600 | C26—C27 | 1.379 (6) |
N4—C20 | 1.470 (5) | C27—C28 | 1.358 (7) |
C11—C12 | 1.464 (7) | C27—H27A | 0.9300 |
C11—H11A | 0.9600 | C28—C29 | 1.358 (7) |
C11—H11B | 0.9600 | C28—H28A | 0.9300 |
C11—H11C | 0.9600 | C29—C30 | 1.385 (6) |
C12—C13 | 1.518 (6) | C29—H29A | 0.9300 |
C12—H12A | 0.9700 | C30—H30A | 0.9300 |
C12—H12B | 0.9700 | ||
C4—N1—C3 | 122.6 (4) | H13A—C13—H13B | 108.0 |
C4—N1—H1A | 118.7 | O4—C14—N3 | 125.0 (4) |
C3—N1—H1A | 118.7 | O4—C14—C15 | 119.1 (4) |
O3—N2—O2 | 123.7 (4) | N3—C14—C15 | 115.8 (3) |
O3—N2—C10 | 119.4 (4) | C20—C15—C16 | 116.6 (4) |
O2—N2—C10 | 116.9 (4) | C20—C15—C14 | 124.8 (4) |
C2—C1—H1B | 109.5 | C16—C15—C14 | 118.6 (4) |
C2—C1—H1C | 109.5 | C15—C16—C17 | 120.8 (4) |
H1B—C1—H1C | 109.5 | C15—C16—H16A | 119.6 |
C2—C1—H1D | 109.5 | C17—C16—H16A | 119.6 |
H1B—C1—H1D | 109.5 | C18—C17—C16 | 120.8 (4) |
H1C—C1—H1D | 109.5 | C18—C17—H17A | 119.6 |
C3—C2—C1 | 116.0 (5) | C16—C17—H17A | 119.6 |
C3—C2—H2A | 108.3 | C19—C18—C17 | 119.3 (4) |
C1—C2—H2A | 108.3 | C19—C18—H18A | 120.4 |
C3—C2—H2B | 108.3 | C17—C18—H18A | 120.4 |
C1—C2—H2B | 108.3 | C18—C19—C20 | 119.5 (4) |
H2A—C2—H2B | 107.4 | C18—C19—H19A | 120.3 |
C2—C3—N1 | 113.6 (4) | C20—C19—H19A | 120.3 |
C2—C3—H3A | 108.8 | C19—C20—C15 | 123.0 (4) |
N1—C3—H3A | 108.8 | C19—C20—N4 | 117.3 (4) |
C2—C3—H3B | 108.8 | C15—C20—N4 | 119.7 (4) |
N1—C3—H3B | 108.8 | C24—N5—C23 | 122.0 (3) |
H3A—C3—H3B | 107.7 | C24—N5—H5A | 119.0 |
O1—C4—N1 | 124.7 (4) | C23—N5—H5A | 119.0 |
O1—C4—C5 | 119.6 (4) | O9—N6—O8 | 124.1 (5) |
N1—C4—C5 | 115.5 (3) | O9—N6—C26 | 118.1 (4) |
C10—C5—C6 | 116.4 (4) | O8—N6—C26 | 117.8 (5) |
C10—C5—C4 | 127.6 (4) | C22—C21—H21A | 109.5 |
C6—C5—C4 | 116.0 (4) | C22—C21—H21B | 109.5 |
C7—C6—C5 | 120.9 (4) | H21A—C21—H21B | 109.5 |
C7—C6—H6A | 119.5 | C22—C21—H21C | 109.5 |
C5—C6—H6A | 119.5 | H21A—C21—H21C | 109.5 |
C8—C7—C6 | 119.6 (5) | H21B—C21—H21C | 109.5 |
C8—C7—H7A | 120.2 | C23—C22—C21 | 111.7 (4) |
C6—C7—H7A | 120.2 | C23—C22—H22A | 109.3 |
C9—C8—C7 | 120.8 (5) | C21—C22—H22A | 109.3 |
C9—C8—H8A | 119.6 | C23—C22—H22B | 109.3 |
C7—C8—H8A | 119.6 | C21—C22—H22B | 109.3 |
C8—C9—C10 | 119.6 (4) | H22A—C22—H22B | 107.9 |
C8—C9—H9A | 120.2 | C22—C23—N5 | 114.4 (4) |
C10—C9—H9A | 120.2 | C22—C23—H23A | 108.7 |
C9—C10—C5 | 122.6 (4) | N5—C23—H23A | 108.7 |
C9—C10—N2 | 117.9 (4) | C22—C23—H23B | 108.7 |
C5—C10—N2 | 119.4 (4) | N5—C23—H23B | 108.7 |
C14—N3—C13 | 122.8 (3) | H23A—C23—H23B | 107.6 |
C14—N3—H3C | 118.6 | O7—C24—N5 | 123.8 (4) |
C13—N3—H3C | 118.6 | O7—C24—C25 | 120.4 (4) |
O5—N4—O6 | 122.6 (5) | N5—C24—C25 | 115.7 (3) |
O5—N4—C20 | 118.1 (4) | C26—C25—C30 | 117.0 (4) |
O6—N4—C20 | 119.3 (4) | C26—C25—C24 | 126.2 (4) |
C12—C11—H11A | 109.5 | C30—C25—C24 | 116.7 (4) |
C12—C11—H11B | 109.5 | C25—C26—C27 | 123.2 (4) |
H11A—C11—H11B | 109.5 | C25—C26—N6 | 119.9 (4) |
C12—C11—H11C | 109.5 | C27—C26—N6 | 116.8 (4) |
H11A—C11—H11C | 109.5 | C28—C27—C26 | 118.1 (5) |
H11B—C11—H11C | 109.5 | C28—C27—H27A | 121.0 |
C11—C12—C13 | 114.4 (5) | C26—C27—H27A | 121.0 |
C11—C12—H12A | 108.7 | C27—C28—C29 | 121.1 (5) |
C13—C12—H12A | 108.7 | C27—C28—H28A | 119.5 |
C11—C12—H12B | 108.7 | C29—C28—H28A | 119.5 |
C13—C12—H12B | 108.7 | C28—C29—C30 | 119.7 (5) |
H12A—C12—H12B | 107.6 | C28—C29—H29A | 120.1 |
N3—C13—C12 | 111.7 (4) | C30—C29—H29A | 120.1 |
N3—C13—H13A | 109.3 | C25—C30—C29 | 120.8 (4) |
C12—C13—H13A | 109.3 | C25—C30—H30A | 119.6 |
N3—C13—H13B | 109.3 | C29—C30—H30A | 119.6 |
C12—C13—H13B | 109.3 | ||
C1—C2—C3—N1 | 179.2 (5) | C17—C18—C19—C20 | −1.0 (6) |
C4—N1—C3—C2 | 97.2 (6) | C18—C19—C20—C15 | −0.3 (6) |
C3—N1—C4—O1 | 3.3 (7) | C18—C19—C20—N4 | −179.3 (4) |
C3—N1—C4—C5 | 179.1 (4) | C16—C15—C20—C19 | 1.3 (6) |
O1—C4—C5—C10 | −114.7 (5) | C14—C15—C20—C19 | −177.6 (4) |
N1—C4—C5—C10 | 69.3 (6) | C16—C15—C20—N4 | −179.7 (4) |
O1—C4—C5—C6 | 64.3 (6) | C14—C15—C20—N4 | 1.3 (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—C19 | 148.1 (4) |
C4—C5—C6—C7 | 179.9 (4) | O5—N4—C20—C15 | 151.1 (5) |
C5—C6—C7—C8 | 0.2 (8) | O6—N4—C20—C15 | −31.0 (6) |
C6—C7—C8—C9 | 0.3 (8) | C21—C22—C23—N5 | −176.0 (4) |
C7—C8—C9—C10 | 0.1 (7) | C24—N5—C23—C22 | −141.0 (5) |
C8—C9—C10—C5 | −0.9 (7) | C23—N5—C24—O7 | 6.1 (7) |
C8—C9—C10—N2 | 175.7 (4) | C23—N5—C24—C25 | −175.4 (4) |
C6—C5—C10—C9 | 1.4 (6) | O7—C24—C25—C26 | −110.9 (5) |
C4—C5—C10—C9 | −179.6 (4) | N5—C24—C25—C26 | 70.5 (5) |
C6—C5—C10—N2 | −175.2 (4) | O7—C24—C25—C30 | 66.7 (5) |
C4—C5—C10—N2 | 3.9 (6) | N5—C24—C25—C30 | −111.9 (4) |
O3—N2—C10—C9 | −158.9 (4) | C30—C25—C26—C27 | 0.9 (6) |
O2—N2—C10—C9 | 23.5 (6) | C24—C25—C26—C27 | 178.5 (4) |
O3—N2—C10—C5 | 17.8 (6) | C30—C25—C26—N6 | −176.6 (4) |
O2—N2—C10—C5 | −159.8 (4) | C24—C25—C26—N6 | 1.1 (6) |
C14—N3—C13—C12 | −106.3 (5) | O9—N6—C26—C25 | 21.4 (6) |
C11—C12—C13—N3 | 178.8 (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—C15 | 177.1 (4) | O8—N6—C26—C27 | 22.9 (6) |
O4—C14—C15—C20 | 106.6 (5) | C25—C26—C27—C28 | −1.5 (7) |
N3—C14—C15—C20 | −76.5 (5) | N6—C26—C27—C28 | 176.0 (4) |
O4—C14—C15—C16 | −72.3 (5) | C26—C27—C28—C29 | 1.5 (8) |
N3—C14—C15—C16 | 104.6 (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—C17 | 177.9 (4) | C24—C25—C30—C29 | −178.1 (4) |
C15—C16—C17—C18 | −0.1 (7) | C28—C29—C30—C25 | 0.2 (7) |
C16—C17—C18—C19 | 1.2 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O4i | 0.86 | 2.02 | 2.854 (5) | 163 |
N3—H3C···O1 | 0.86 | 1.98 | 2.840 (4) | 177 |
N5—H5A···O7ii | 0.86 | 2.04 | 2.843 (4) | 154 |
C6—H6A···Cg2 | 0.93 | 2.86 | 3.751 (5) | 162 |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C10H12N2O3 |
Mr | 208.22 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 15.835 (3), 9.3910 (19), 23.618 (5) |
β (°) | 108.35 (3) |
V (Å3) | 3333.6 (12) |
Z | 12 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.30 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.973, 0.991 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6289, 6056, 2855 |
Rint | 0.060 |
(sin θ/λ)max (Å−1) | 0.602 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.079, 0.188, 1.00 |
No. of reflections | 6056 |
No. of parameters | 388 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.29, −0.56 |
Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O4i | 0.86 | 2.02 | 2.854 (5) | 163 |
N3—H3C···O1 | 0.86 | 1.98 | 2.840 (4) | 177 |
N5—H5A···O7ii | 0.86 | 2.04 | 2.843 (4) | 154 |
C6—H6A···Cg2 | 0.93 | 2.86 | 3.751 (5) | 162 |
Symmetry codes: (i) x, y+1, z; (ii) −x+1, y−1/2, −z+1/2. |
Acknowledgements
The authors thank the Center of Testing and Analysis, Nanjing University, for support.
References
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Enraf–Nonius (1985). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Goodman, C. R. & Serafini, T. (2004). Renovis, INT., San Francisco, US. CA Patent No. 2 510 042. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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).