Acta Cryst. (2007). E63, o3364 [ doi:10.1107/S1600536807031649 ]
The conformation of the N-H bond in the structure of the title compound, C8H7ClN2O3, is anti to the meta-nitro group, in contrast with the syn conformation observed with respect to the ortho-nitro substituent in 2-chloro-N-(2-nitrophenyl)acetamide. The geometric parameters of the title compound are similar to those of 2-chloro-N-(4-nitrophenyl)acetamide and other acetanilides. Intermolecular N-H
O hydrogen bonds link the molecules into zigzag chains running along the a and b axes.
The title compound was prepared according to the literature method (Gowda & Weiss, 1994). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NQR spectra (Gowda & Weiss, 1994). Single crystals of the title compound were obtained from an ethanolic solution and used for X-ray diffraction studies at room temperature.
The H atoms were positioned with idealized geometry using a riding model with N—H = 0.86 Å and C—H = 0.93–0.97 Å]. Uiso(H) values were set equal to 1.2Ueq of the parent atom.
Data collection: CAD-4-PC Software (Enraf–Nonius, 1996); cell refinement: CAD-4-PC Software; data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
![[Figure 1]](./bt2406fig1thm.gif)
| Fig. 1. Molecular structure of the title compound showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii. |
![[Figure 2]](./bt2406fig2thm.gif)
| Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines. |
| C8H7ClN2O3 | Dx = 1.590 Mg m−3 |
| Mr = 214.61 | Cu Kα radiation, λ = 1.54180 Å |
| Tetragonal, P43 | Cell parameters from 25 reflections |
| Hall symbol: P 4cw | θ = 9.0–25.8° |
| a = 4.999 (2) Å | µ = 3.67 mm−1 |
| c = 35.876 (6) Å | T = 299 K |
| V = 896.5 (5) Å3 | Prism, dark orange |
| Z = 4 | 0.60 × 0.60 × 0.45 mm |
| F(000) = 440 |
| Enraf–Nonius CAD-4 diffractometer | 686 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.162 |
| graphite | θmax = 67.1°, θmin = 4.9° |
| ω/2θ scans | h = 0→5 |
| Absorption correction: ψ scan (North et al., 1968) | k = −5→5 |
| Tmin = 0.220, Tmax = 0.276 | l = −42→0 |
| 1784 measured reflections | 3 standard reflections every 120 min |
| 810 independent reflections | intensity decay: 1.0% |
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.066 | w = 1/[σ2(Fo2) + (0.078P)2 + 0.1695P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.188 | (Δ/σ)max < 0.001 |
| S = 1.13 | Δρmax = 0.31 e Å−3 |
| 810 reflections | Δρmin = −0.40 e Å−3 |
| 128 parameters | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| 1 restraint | Extinction coefficient: 0.022 (5) |
| Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), with no Friedel pairs |
| Secondary atom site location: difference Fourier map | Flack parameter: 0.03 (4) |
| C8H7ClN2O3 | Z = 4 |
| Mr = 214.61 | Cu Kα radiation |
| Tetragonal, P43 | µ = 3.67 mm−1 |
| a = 4.999 (2) Å | T = 299 K |
| c = 35.876 (6) Å | 0.60 × 0.60 × 0.45 mm |
| V = 896.5 (5) Å3 |
| Enraf–Nonius CAD-4 diffractometer | 686 reflections with I > 2σ(I) |
| Absorption correction: ψ scan (North et al., 1968) | Rint = 0.162 |
| Tmin = 0.220, Tmax = 0.276 | θmax = 67.1° |
| 1784 measured reflections | 3 standard reflections every 120 min |
| 810 independent reflections | intensity decay: 1.0% |
| R[F2 > 2σ(F2)] = 0.066 | H-atom parameters constrained |
| wR(F2) = 0.188 | Δρmax = 0.31 e Å−3 |
| S = 1.13 | Δρmin = −0.40 e Å−3 |
| 810 reflections | Absolute structure: Flack (1983), with no Friedel pairs |
| 128 parameters | Flack parameter: 0.03 (4) |
| 1 restraint |
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 | ||
| C2 | −0.3115 (17) | 0.3054 (16) | 0.15620 (18) | 0.058 (2) | |
| H2B | −0.3817 | 0.4858 | 0.1543 | 0.070* | |
| H2A | −0.1869 | 0.3003 | 0.1769 | 0.070* | |
| C3 | −0.1668 (14) | 0.2336 (13) | 0.12061 (17) | 0.0444 (16) | |
| C6 | 0.1238 (13) | 0.4335 (12) | 0.07257 (17) | 0.0414 (14) | |
| C7 | 0.0760 (14) | 0.2529 (14) | 0.04397 (18) | 0.0487 (16) | |
| H7 | −0.0619 | 0.1287 | 0.0457 | 0.058* | |
| C8 | 0.2381 (14) | 0.2624 (15) | 0.01301 (17) | 0.0484 (16) | |
| C9 | 0.4455 (15) | 0.4393 (16) | 0.0093 (3) | 0.062 (2) | |
| H9 | 0.5530 | 0.4392 | −0.0118 | 0.074* | |
| C10 | 0.4895 (17) | 0.6160 (16) | 0.0377 (2) | 0.061 (2) | |
| H10 | 0.6290 | 0.7382 | 0.0358 | 0.073* | |
| C11 | 0.3318 (14) | 0.6165 (12) | 0.0690 (2) | 0.0505 (16) | |
| H11 | 0.3641 | 0.7397 | 0.0879 | 0.061* | |
| Cl1 | −0.5750 (3) | 0.0811 (4) | 0.16453 (4) | 0.0687 (8) | |
| N5 | −0.0402 (12) | 0.4416 (10) | 0.10456 (15) | 0.0455 (14) | |
| H5N | −0.0616 | 0.5954 | 0.1149 | 0.055* | |
| N12 | 0.1788 (14) | 0.0720 (13) | −0.01703 (17) | 0.0581 (16) | |
| O4 | −0.1610 (12) | 0.0095 (10) | 0.10761 (15) | 0.0587 (14) | |
| O13 | −0.0164 (16) | −0.0715 (14) | −0.01436 (19) | 0.083 (2) | |
| O14 | 0.3341 (15) | 0.0670 (15) | −0.04350 (16) | 0.084 (2) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C2 | 0.065 (5) | 0.049 (4) | 0.061 (4) | −0.003 (4) | 0.008 (3) | −0.008 (3) |
| C3 | 0.045 (4) | 0.031 (3) | 0.058 (3) | −0.001 (2) | −0.003 (3) | −0.007 (3) |
| C6 | 0.039 (3) | 0.030 (3) | 0.055 (3) | 0.003 (2) | 0.000 (3) | 0.002 (3) |
| C7 | 0.043 (4) | 0.043 (3) | 0.060 (3) | 0.006 (3) | 0.000 (3) | −0.001 (3) |
| C8 | 0.047 (4) | 0.044 (3) | 0.054 (3) | 0.012 (3) | −0.001 (3) | 0.000 (3) |
| C9 | 0.040 (4) | 0.062 (5) | 0.082 (4) | 0.012 (4) | 0.008 (3) | 0.021 (4) |
| C10 | 0.049 (4) | 0.048 (4) | 0.086 (5) | −0.003 (4) | 0.002 (4) | 0.010 (4) |
| C11 | 0.045 (4) | 0.027 (3) | 0.079 (4) | 0.002 (3) | −0.006 (3) | −0.001 (3) |
| Cl1 | 0.0534 (13) | 0.0763 (15) | 0.0765 (11) | −0.0104 (8) | 0.0105 (8) | −0.0069 (9) |
| N5 | 0.053 (3) | 0.028 (3) | 0.055 (3) | −0.001 (2) | 0.001 (3) | −0.008 (2) |
| N12 | 0.061 (4) | 0.054 (4) | 0.059 (3) | 0.019 (3) | −0.006 (3) | −0.002 (3) |
| O4 | 0.067 (3) | 0.035 (3) | 0.074 (3) | 0.000 (2) | 0.011 (3) | −0.004 (2) |
| O13 | 0.084 (4) | 0.077 (5) | 0.086 (4) | −0.012 (4) | −0.007 (4) | −0.022 (3) |
| O14 | 0.083 (4) | 0.103 (5) | 0.067 (3) | 0.029 (4) | 0.022 (3) | −0.014 (3) |
| C2—C3 | 1.510 (9) | C8—C9 | 1.369 (11) |
| C2—Cl1 | 1.756 (8) | C8—N12 | 1.468 (10) |
| C2—H2B | 0.9700 | C9—C10 | 1.365 (13) |
| C2—H2A | 0.9700 | C9—H9 | 0.9300 |
| C3—O4 | 1.214 (8) | C10—C11 | 1.372 (12) |
| C3—N5 | 1.347 (9) | C10—H10 | 0.9300 |
| C6—C7 | 1.388 (9) | C11—H11 | 0.9300 |
| C6—C11 | 1.391 (9) | N5—H5N | 0.8600 |
| C6—N5 | 1.411 (9) | N12—O13 | 1.215 (10) |
| C7—C8 | 1.376 (9) | N12—O14 | 1.227 (9) |
| C7—H7 | 0.9300 | ||
| C3—C2—Cl1 | 110.6 (5) | C7—C8—N12 | 116.8 (7) |
| C3—C2—H2B | 109.5 | C10—C9—C8 | 117.9 (8) |
| Cl1—C2—H2B | 109.5 | C10—C9—H9 | 121.1 |
| C3—C2—H2A | 109.5 | C8—C9—H9 | 121.1 |
| Cl1—C2—H2A | 109.5 | C9—C10—C11 | 121.3 (8) |
| H2B—C2—H2A | 108.1 | C9—C10—H10 | 119.4 |
| O4—C3—N5 | 122.5 (6) | C11—C10—H10 | 119.4 |
| O4—C3—C2 | 123.7 (6) | C10—C11—C6 | 120.3 (7) |
| N5—C3—C2 | 113.8 (6) | C10—C11—H11 | 119.9 |
| C7—C6—C11 | 119.2 (6) | C6—C11—H11 | 119.9 |
| C7—C6—N5 | 121.3 (6) | C3—N5—C6 | 126.8 (5) |
| C11—C6—N5 | 119.4 (6) | C3—N5—H5N | 116.6 |
| C8—C7—C6 | 118.2 (6) | C6—N5—H5N | 116.6 |
| C8—C7—H7 | 120.9 | O13—N12—O14 | 123.9 (7) |
| C6—C7—H7 | 120.9 | O13—N12—C8 | 119.1 (6) |
| C9—C8—C7 | 123.1 (7) | O14—N12—C8 | 117.0 (7) |
| C9—C8—N12 | 120.0 (7) | ||
| Cl1—C2—C3—O4 | −25.7 (9) | C7—C6—C11—C10 | −0.7 (10) |
| Cl1—C2—C3—N5 | 155.1 (5) | N5—C6—C11—C10 | −178.4 (6) |
| C11—C6—C7—C8 | 0.1 (9) | O4—C3—N5—C6 | −3.3 (11) |
| N5—C6—C7—C8 | 177.7 (6) | C2—C3—N5—C6 | 175.9 (7) |
| C6—C7—C8—C9 | 0.8 (10) | C7—C6—N5—C3 | 32.2 (10) |
| C6—C7—C8—N12 | −178.9 (6) | C11—C6—N5—C3 | −150.1 (6) |
| C7—C8—C9—C10 | −0.9 (11) | C9—C8—N12—O13 | −175.2 (8) |
| N12—C8—C9—C10 | 178.8 (7) | C7—C8—N12—O13 | 4.4 (10) |
| C8—C9—C10—C11 | 0.1 (11) | C9—C8—N12—O14 | 5.4 (9) |
| C9—C10—C11—C6 | 0.6 (11) | C7—C8—N12—O14 | −175.0 (6) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N5—H5N···O4i | 0.86 | 2.14 | 2.904 (7) | 147 |
| Symmetry codes: (i) x, y+1, z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N5—H5N···O4i | 0.86 | 2.14 | 2.904 (7) | 147 |
| Symmetry codes: (i) x, y+1, z. |
BTG gratefully thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.
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The amide moiety is an important constituent of many biologically significant compounds. The structural studies of amides are therefore of interest. As part of a study of the effect of ring and side chain substitutions on the solid state structures of this class of compounds (Gowda et al., 2007a,b,c,d), the crystal structure of N-(3-nitrophenyl)-2-chloroacetamide has been determined to explore the effects of polar substituent groups on the structures of N-aromatic amides. The conformation of the N—H bond (Fig. 1) is anti to the meta nitro group, in contrast to the syn conformation observed with respect to ortho nitro substituent in N-(2-nitrophenyl)-2-chloroacetamide (Gowda et al., 2007a). The geometric parameters of are similar to those of N-(2-nitrophenyl)-2-chloroacetamide (Gowda et al., 2007a), N-(4-nitrophenyl)-2-chloroacetamide (Gowda et al., 2007c) and other acetanilides (Gowda et al., 2007b, Gowda et al., 2007). The molecular skeleton is essentially planar. Intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into zigzag chains running along the a and b axis (Fig. 2).