Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807041372/cv2289sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807041372/cv2289Isup2.hkl |
CCDC reference: 660362
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.004 Å
- R factor = 0.050
- wR factor = 0.147
- Data-to-parameter ratio = 12.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For crystal structures of related amides, see: Guo (2004); Gowda et al. (2007). For normal ranges of molecular bond lengths and angles, see: Allen et al. (1987).
The title compound was prepared by the following procedure. The mixture of concentrated sulfuric acid (1.9 ml) and nitric acid (1.4 ml) was added dropwise into a solution of concentrated sulfuric acid (8 ml) and N-phenylpropionamid (3.5 g) with stirring at 0° C temperature. After the acid was added out, intermittently shake the mixture system for 30 min at the room temperature. The mixture was dispersed in ice water (50 ml), after which 4.3 g of the yellow powder product was separated by filtration. The product (0.3 g) was heated and dissolved in ethanol (15 ml). Single crystals were obtained by slow concentration over a period of 3 d at room temperature.
The H atom of the NH group was found in a difference Fourier map, but placed in idealized position with N—H = 0.86 Å, and its Uiso value was set at 1.2Ueq(N). The C-bound H atoms were included in the refinement in the riding model approximation, with C–H = 0.93–0.97 Å and Uiso (H) = 1.2 Ueq (C) or 1.5Ueq(Cmethyl).
The structural studies of amides are of interest (Gowda et al., 2007). As a part of our study of new possible drugs (Guo, 2004), the crystal structure of the title compound (I) is reported herein.
The atom-numbering scheme of the title compound, (I), is illustrated in Fig. 1. The bond distances and angles are normal, within experimental error (Allen et al., 1987).
The intermolecular N1—H1A···O1i hydrogen bond (Table 1) link the molecules into chains (Fig. 2) in the a direction. Further, C5—H5···O2ii controls the packing in the structure.
For crystal structures of related amides, see: Guo (2004); Gowda et al. (2007). For normal ranges of molecular bond lengths and angles, see: Allen et al. (1987).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL (Bruker, 2001); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).
C9H10N2O3 | F(000) = 816 |
Mr = 194.19 | Dx = 1.383 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 2057 reflections |
a = 9.763 (3) Å | θ = 2.9–24.5° |
b = 9.278 (3) Å | µ = 0.11 mm−1 |
c = 20.586 (5) Å | T = 294 K |
V = 1864.7 (9) Å3 | Prism, yellow |
Z = 8 | 0.20 × 0.16 × 0.12 mm |
Bruker SMART CCD area-detector diffractometer | 1641 independent reflections |
Radiation source: fine-focus sealed tube | 1017 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.081 |
φ and ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.982, Tmax = 0.991 | k = −10→11 |
8729 measured reflections | l = −17→24 |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.147 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0529P)2 + 0.9116P] where P = (Fo2 + 2Fc2)/3 |
1641 reflections | (Δ/σ)max < 0.001 |
127 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C9H10N2O3 | V = 1864.7 (9) Å3 |
Mr = 194.19 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 9.763 (3) Å | µ = 0.11 mm−1 |
b = 9.278 (3) Å | T = 294 K |
c = 20.586 (5) Å | 0.20 × 0.16 × 0.12 mm |
Bruker SMART CCD area-detector diffractometer | 1641 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1017 reflections with I > 2σ(I) |
Tmin = 0.982, Tmax = 0.991 | Rint = 0.081 |
8729 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.147 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.15 e Å−3 |
1641 reflections | Δρmin = −0.20 e Å−3 |
127 parameters |
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 | ||
N1 | 0.18357 (19) | 0.9563 (2) | 0.29421 (10) | 0.0490 (6) | |
H1A | 0.1012 | 0.9815 | 0.2834 | 0.059* | |
N2 | 0.2399 (3) | 0.5853 (3) | 0.50795 (12) | 0.0682 (7) | |
O1 | 0.39868 (18) | 0.9788 (2) | 0.25400 (9) | 0.0669 (6) | |
O2 | 0.1359 (2) | 0.5464 (3) | 0.53559 (11) | 0.0961 (9) | |
O3 | 0.3528 (3) | 0.5507 (3) | 0.52575 (13) | 0.1157 (11) | |
C1 | 0.2042 (2) | 0.8624 (3) | 0.34674 (12) | 0.0454 (6) | |
C2 | 0.3325 (3) | 0.8307 (3) | 0.37243 (13) | 0.0571 (8) | |
H2 | 0.4107 | 0.8714 | 0.3544 | 0.069* | |
C3 | 0.3431 (3) | 0.7388 (3) | 0.42472 (13) | 0.0610 (8) | |
H3 | 0.4286 | 0.7164 | 0.4418 | 0.073* | |
C4 | 0.2270 (3) | 0.6805 (3) | 0.45151 (12) | 0.0517 (7) | |
C5 | 0.0993 (3) | 0.7117 (3) | 0.42755 (14) | 0.0628 (8) | |
H5 | 0.0213 | 0.6728 | 0.4467 | 0.075* | |
C6 | 0.0888 (3) | 0.8013 (3) | 0.37478 (13) | 0.0571 (8) | |
H6 | 0.0028 | 0.8214 | 0.3575 | 0.069* | |
C7 | 0.2767 (2) | 1.0102 (3) | 0.25161 (13) | 0.0482 (7) | |
C8 | 0.2166 (3) | 1.1091 (3) | 0.20158 (13) | 0.0621 (8) | |
H8A | 0.1601 | 1.1802 | 0.2234 | 0.074* | |
H8B | 0.1576 | 1.0534 | 0.1732 | 0.074* | |
C9 | 0.3215 (4) | 1.1863 (4) | 0.16084 (15) | 0.0781 (10) | |
H9A | 0.3810 | 1.2412 | 0.1885 | 0.117* | |
H9B | 0.2760 | 1.2498 | 0.1310 | 0.117* | |
H9C | 0.3745 | 1.1170 | 0.1370 | 0.117* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0357 (11) | 0.0592 (14) | 0.0521 (13) | 0.0042 (10) | 0.0024 (10) | 0.0042 (11) |
N2 | 0.0761 (18) | 0.0759 (18) | 0.0526 (15) | −0.0125 (15) | −0.0074 (15) | 0.0018 (13) |
O1 | 0.0400 (11) | 0.0934 (16) | 0.0671 (12) | 0.0023 (10) | 0.0083 (9) | 0.0103 (11) |
O2 | 0.0899 (17) | 0.125 (2) | 0.0737 (16) | −0.0340 (16) | −0.0031 (13) | 0.0328 (14) |
O3 | 0.0864 (18) | 0.156 (3) | 0.105 (2) | 0.0068 (18) | −0.0091 (15) | 0.0637 (19) |
C1 | 0.0402 (14) | 0.0492 (15) | 0.0470 (14) | −0.0025 (12) | 0.0020 (11) | −0.0107 (12) |
C2 | 0.0388 (15) | 0.077 (2) | 0.0559 (16) | −0.0029 (14) | 0.0029 (12) | 0.0080 (15) |
C3 | 0.0468 (16) | 0.082 (2) | 0.0541 (17) | 0.0034 (15) | −0.0014 (13) | −0.0003 (16) |
C4 | 0.0583 (17) | 0.0542 (17) | 0.0426 (14) | −0.0076 (14) | −0.0006 (12) | −0.0047 (13) |
C5 | 0.0494 (16) | 0.079 (2) | 0.0599 (18) | −0.0151 (15) | 0.0022 (14) | 0.0044 (16) |
C6 | 0.0384 (14) | 0.075 (2) | 0.0584 (17) | −0.0057 (13) | 0.0009 (13) | 0.0062 (15) |
C7 | 0.0415 (15) | 0.0529 (16) | 0.0504 (14) | −0.0009 (12) | 0.0038 (12) | −0.0063 (13) |
C8 | 0.0606 (18) | 0.0648 (19) | 0.0608 (17) | −0.0031 (15) | 0.0014 (14) | 0.0095 (15) |
C9 | 0.093 (2) | 0.073 (2) | 0.068 (2) | −0.0058 (19) | 0.0159 (18) | 0.0125 (17) |
N1—C7 | 1.359 (3) | C3—H3 | 0.9300 |
N1—C1 | 1.403 (3) | C4—C5 | 1.372 (4) |
N1—H1A | 0.8670 | C5—C6 | 1.372 (4) |
N2—O3 | 1.206 (3) | C5—H5 | 0.9300 |
N2—O2 | 1.218 (3) | C6—H6 | 0.9300 |
N2—C4 | 1.465 (4) | C7—C8 | 1.499 (4) |
O1—C7 | 1.227 (3) | C8—C9 | 1.505 (4) |
C1—C6 | 1.387 (3) | C8—H8A | 0.9700 |
C1—C2 | 1.391 (3) | C8—H8B | 0.9700 |
C2—C3 | 1.377 (4) | C9—H9A | 0.9600 |
C2—H2 | 0.9300 | C9—H9B | 0.9600 |
C3—C4 | 1.371 (4) | C9—H9C | 0.9600 |
C7—N1—C1 | 129.1 (2) | C6—C5—H5 | 120.6 |
C7—N1—H1A | 110.8 | C5—C6—C1 | 121.1 (3) |
C1—N1—H1A | 119.9 | C5—C6—H6 | 119.5 |
O3—N2—O2 | 122.8 (3) | C1—C6—H6 | 119.5 |
O3—N2—C4 | 118.7 (3) | O1—C7—N1 | 122.4 (2) |
O2—N2—C4 | 118.5 (3) | O1—C7—C8 | 123.6 (2) |
C6—C1—C2 | 119.1 (2) | N1—C7—C8 | 114.0 (2) |
C6—C1—N1 | 117.3 (2) | C7—C8—C9 | 114.0 (2) |
C2—C1—N1 | 123.6 (2) | C7—C8—H8A | 108.7 |
C3—C2—C1 | 119.7 (3) | C9—C8—H8A | 108.7 |
C3—C2—H2 | 120.1 | C7—C8—H8B | 108.7 |
C1—C2—H2 | 120.1 | C9—C8—H8B | 108.7 |
C4—C3—C2 | 119.8 (3) | H8A—C8—H8B | 107.6 |
C4—C3—H3 | 120.1 | C8—C9—H9A | 109.5 |
C2—C3—H3 | 120.1 | C8—C9—H9B | 109.5 |
C3—C4—C5 | 121.5 (3) | H9A—C9—H9B | 109.5 |
C3—C4—N2 | 119.1 (3) | C8—C9—H9C | 109.5 |
C5—C4—N2 | 119.3 (2) | H9A—C9—H9C | 109.5 |
C4—C5—C6 | 118.7 (3) | H9B—C9—H9C | 109.5 |
C4—C5—H5 | 120.6 | ||
C7—N1—C1—C6 | −167.6 (2) | O2—N2—C4—C5 | −6.3 (4) |
C7—N1—C1—C2 | 13.8 (4) | C3—C4—C5—C6 | 1.2 (4) |
C6—C1—C2—C3 | 0.5 (4) | N2—C4—C5—C6 | 179.8 (3) |
N1—C1—C2—C3 | 179.0 (2) | C4—C5—C6—C1 | −1.4 (4) |
C1—C2—C3—C4 | −0.7 (4) | C2—C1—C6—C5 | 0.6 (4) |
C2—C3—C4—C5 | −0.2 (4) | N1—C1—C6—C5 | −178.1 (2) |
C2—C3—C4—N2 | −178.8 (3) | C1—N1—C7—O1 | 1.1 (4) |
O3—N2—C4—C3 | −6.5 (4) | C1—N1—C7—C8 | −179.6 (2) |
O2—N2—C4—C3 | 172.3 (3) | O1—C7—C8—C9 | −9.5 (4) |
O3—N2—C4—C5 | 174.9 (3) | N1—C7—C8—C9 | 171.3 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.87 | 2.12 | 2.960 (3) | 163 |
C5—H5···O2ii | 0.93 | 2.57 | 3.403 (4) | 149 |
Symmetry codes: (i) x−1/2, y, −z+1/2; (ii) −x, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C9H10N2O3 |
Mr | 194.19 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 294 |
a, b, c (Å) | 9.763 (3), 9.278 (3), 20.586 (5) |
V (Å3) | 1864.7 (9) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.20 × 0.16 × 0.12 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.982, 0.991 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8729, 1641, 1017 |
Rint | 0.081 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.147, 1.04 |
No. of reflections | 1641 |
No. of parameters | 127 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.15, −0.20 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXTL (Bruker, 2001).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.87 | 2.12 | 2.960 (3) | 162.7 |
C5—H5···O2ii | 0.93 | 2.57 | 3.403 (4) | 148.7 |
Symmetry codes: (i) x−1/2, y, −z+1/2; (ii) −x, −y+1, −z+1. |
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The structural studies of amides are of interest (Gowda et al., 2007). As a part of our study of new possible drugs (Guo, 2004), the crystal structure of the title compound (I) is reported herein.
The atom-numbering scheme of the title compound, (I), is illustrated in Fig. 1. The bond distances and angles are normal, within experimental error (Allen et al., 1987).
The intermolecular N1—H1A···O1i hydrogen bond (Table 1) link the molecules into chains (Fig. 2) in the a direction. Further, C5—H5···O2ii controls the packing in the structure.