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In the title compound, C9H10N2O3, the mean planes of the propionamide fragment and the benzene ring make a dihedral angle of 12.86 (2)°. The crystal packing exhibits inter­molecular N—H...O hydrogen bonds, which link the mol­ecules into linear chains extended along the a axis, and weak C—H...O inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807041372/cv2289sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807041372/cv2289Isup2.hkl
Contains datablock I

CCDC reference: 660362

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](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

Comment top

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.

Related literature top

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).

Experimental top

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.

Refinement top

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).

Structure description top

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).

Computing details top

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).

Figures top
[Figure 1] Fig. 1. A view of the structure of (I), showing the atom-numbering scheme. Displacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. Packing diagram showing hydrogen bonds interactions drawn as dashed lines, viewed down the b axis.
N-(4-Nitrophenyl)propionamide top
Crystal data top
C9H10N2O3F(000) = 816
Mr = 194.19Dx = 1.383 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 2057 reflections
a = 9.763 (3) Åθ = 2.9–24.5°
b = 9.278 (3) ŵ = 0.11 mm1
c = 20.586 (5) ÅT = 294 K
V = 1864.7 (9) Å3Prism, yellow
Z = 80.20 × 0.16 × 0.12 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1641 independent reflections
Radiation source: fine-focus sealed tube1017 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.081
φ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.982, Tmax = 0.991k = 1011
8729 measured reflectionsl = 1724
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H-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 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.20 e Å3
Crystal data top
C9H10N2O3V = 1864.7 (9) Å3
Mr = 194.19Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 9.763 (3) ŵ = 0.11 mm1
b = 9.278 (3) ÅT = 294 K
c = 20.586 (5) Å0.20 × 0.16 × 0.12 mm
Data collection top
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 = 0.991Rint = 0.081
8729 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.147H-atom parameters constrained
S = 1.04Δρmax = 0.15 e Å3
1641 reflectionsΔρmin = 0.20 e Å3
127 parameters
Special details top

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
N10.18357 (19)0.9563 (2)0.29421 (10)0.0490 (6)
H1A0.10120.98150.28340.059*
N20.2399 (3)0.5853 (3)0.50795 (12)0.0682 (7)
O10.39868 (18)0.9788 (2)0.25400 (9)0.0669 (6)
O20.1359 (2)0.5464 (3)0.53559 (11)0.0961 (9)
O30.3528 (3)0.5507 (3)0.52575 (13)0.1157 (11)
C10.2042 (2)0.8624 (3)0.34674 (12)0.0454 (6)
C20.3325 (3)0.8307 (3)0.37243 (13)0.0571 (8)
H20.41070.87140.35440.069*
C30.3431 (3)0.7388 (3)0.42472 (13)0.0610 (8)
H30.42860.71640.44180.073*
C40.2270 (3)0.6805 (3)0.45151 (12)0.0517 (7)
C50.0993 (3)0.7117 (3)0.42755 (14)0.0628 (8)
H50.02130.67280.44670.075*
C60.0888 (3)0.8013 (3)0.37478 (13)0.0571 (8)
H60.00280.82140.35750.069*
C70.2767 (2)1.0102 (3)0.25161 (13)0.0482 (7)
C80.2166 (3)1.1091 (3)0.20158 (13)0.0621 (8)
H8A0.16011.18020.22340.074*
H8B0.15761.05340.17320.074*
C90.3215 (4)1.1863 (4)0.16084 (15)0.0781 (10)
H9A0.38101.24120.18850.117*
H9B0.27601.24980.13100.117*
H9C0.37451.11700.13700.117*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0357 (11)0.0592 (14)0.0521 (13)0.0042 (10)0.0024 (10)0.0042 (11)
N20.0761 (18)0.0759 (18)0.0526 (15)0.0125 (15)0.0074 (15)0.0018 (13)
O10.0400 (11)0.0934 (16)0.0671 (12)0.0023 (10)0.0083 (9)0.0103 (11)
O20.0899 (17)0.125 (2)0.0737 (16)0.0340 (16)0.0031 (13)0.0328 (14)
O30.0864 (18)0.156 (3)0.105 (2)0.0068 (18)0.0091 (15)0.0637 (19)
C10.0402 (14)0.0492 (15)0.0470 (14)0.0025 (12)0.0020 (11)0.0107 (12)
C20.0388 (15)0.077 (2)0.0559 (16)0.0029 (14)0.0029 (12)0.0080 (15)
C30.0468 (16)0.082 (2)0.0541 (17)0.0034 (15)0.0014 (13)0.0003 (16)
C40.0583 (17)0.0542 (17)0.0426 (14)0.0076 (14)0.0006 (12)0.0047 (13)
C50.0494 (16)0.079 (2)0.0599 (18)0.0151 (15)0.0022 (14)0.0044 (16)
C60.0384 (14)0.075 (2)0.0584 (17)0.0057 (13)0.0009 (13)0.0062 (15)
C70.0415 (15)0.0529 (16)0.0504 (14)0.0009 (12)0.0038 (12)0.0063 (13)
C80.0606 (18)0.0648 (19)0.0608 (17)0.0031 (15)0.0014 (14)0.0095 (15)
C90.093 (2)0.073 (2)0.068 (2)0.0058 (19)0.0159 (18)0.0125 (17)
Geometric parameters (Å, º) top
N1—C71.359 (3)C3—H30.9300
N1—C11.403 (3)C4—C51.372 (4)
N1—H1A0.8670C5—C61.372 (4)
N2—O31.206 (3)C5—H50.9300
N2—O21.218 (3)C6—H60.9300
N2—C41.465 (4)C7—C81.499 (4)
O1—C71.227 (3)C8—C91.505 (4)
C1—C61.387 (3)C8—H8A0.9700
C1—C21.391 (3)C8—H8B0.9700
C2—C31.377 (4)C9—H9A0.9600
C2—H20.9300C9—H9B0.9600
C3—C41.371 (4)C9—H9C0.9600
C7—N1—C1129.1 (2)C6—C5—H5120.6
C7—N1—H1A110.8C5—C6—C1121.1 (3)
C1—N1—H1A119.9C5—C6—H6119.5
O3—N2—O2122.8 (3)C1—C6—H6119.5
O3—N2—C4118.7 (3)O1—C7—N1122.4 (2)
O2—N2—C4118.5 (3)O1—C7—C8123.6 (2)
C6—C1—C2119.1 (2)N1—C7—C8114.0 (2)
C6—C1—N1117.3 (2)C7—C8—C9114.0 (2)
C2—C1—N1123.6 (2)C7—C8—H8A108.7
C3—C2—C1119.7 (3)C9—C8—H8A108.7
C3—C2—H2120.1C7—C8—H8B108.7
C1—C2—H2120.1C9—C8—H8B108.7
C4—C3—C2119.8 (3)H8A—C8—H8B107.6
C4—C3—H3120.1C8—C9—H9A109.5
C2—C3—H3120.1C8—C9—H9B109.5
C3—C4—C5121.5 (3)H9A—C9—H9B109.5
C3—C4—N2119.1 (3)C8—C9—H9C109.5
C5—C4—N2119.3 (2)H9A—C9—H9C109.5
C4—C5—C6118.7 (3)H9B—C9—H9C109.5
C4—C5—H5120.6
C7—N1—C1—C6167.6 (2)O2—N2—C4—C56.3 (4)
C7—N1—C1—C213.8 (4)C3—C4—C5—C61.2 (4)
C6—C1—C2—C30.5 (4)N2—C4—C5—C6179.8 (3)
N1—C1—C2—C3179.0 (2)C4—C5—C6—C11.4 (4)
C1—C2—C3—C40.7 (4)C2—C1—C6—C50.6 (4)
C2—C3—C4—C50.2 (4)N1—C1—C6—C5178.1 (2)
C2—C3—C4—N2178.8 (3)C1—N1—C7—O11.1 (4)
O3—N2—C4—C36.5 (4)C1—N1—C7—C8179.6 (2)
O2—N2—C4—C3172.3 (3)O1—C7—C8—C99.5 (4)
O3—N2—C4—C5174.9 (3)N1—C7—C8—C9171.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.872.122.960 (3)163
C5—H5···O2ii0.932.573.403 (4)149
Symmetry codes: (i) x1/2, y, z+1/2; (ii) x, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC9H10N2O3
Mr194.19
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)294
a, b, c (Å)9.763 (3), 9.278 (3), 20.586 (5)
V3)1864.7 (9)
Z8
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.20 × 0.16 × 0.12
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.982, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections
8729, 1641, 1017
Rint0.081
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.147, 1.04
No. of reflections1641
No. of parameters127
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.15, 0.20

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXTL (Bruker, 2001).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.872.122.960 (3)162.7
C5—H5···O2ii0.932.573.403 (4)148.7
Symmetry codes: (i) x1/2, y, z+1/2; (ii) x, y+1, z+1.
 

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