Acta Cryst. (2008). E64, o382 [ doi:10.1107/S160053680706881X ]
The conformation of the N-H bond in the structure of the title compound (3NPDCA), C8H6Cl2N2O3, is anti to the meta-nitro group, similar to that in the structures of 2-chloro-N-(3-nitrophenyl)acetamide (3NPCA) and 2,2,2-trichloro-N-(3-nitrophenyl)acetamide (3NPTCA), and the meta-chloro group in 2,2-dichloro-N-(3-chlorophenyl)acetamide (3CPDCA). The geometric parameters of 3NPDCA are similar to those of 2,2-dichloro-N-phenylacetamide, 3CPDCA, 3NPCA, 3NPTCA and other acetanilides. Intermolecular N-H
O hydrogen bonds link the molecules into chains running along the b axis.
The title compound was prepared similar to the literature method (Gowda and 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 and 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 located in difference map with C—H = 0.89 (3)–0.96 (3) Å and N—H distance was restrained to 0.86 (2) %A. All H atoms were refined with isotropic displacement parameters (set to 1.2 times of the Ueq of the parent atom).
Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXS97 (Sheldrick, 2008).
![[Figure 1]](./dn2307fig1thm.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]](./dn2307fig2thm.gif)
| Fig. 2. Partial packing view showing the hydrogen bonding as dashed lines.H atoms not involved in hydrogen bonding have been omitted for clarity. [Symmetry code: (i) x - 1/2, 1/2 - y,1 - z] |
| C8H6Cl2N2O3 | F000 = 1008 |
| Mr = 249.05 | Dx = 1.627 Mg m−3 |
| Orthorhombic, Pbca | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -P 2ac 2ab | Cell parameters from 4893 reflections |
| a = 9.6092 (6) Å | θ = 2.8–27.8º |
| b = 10.6487 (7) Å | µ = 0.63 mm−1 |
| c = 19.868 (1) Å | T = 299 (2) K |
| V = 2033.0 (2) Å3 | Prism, yellow |
| Z = 8 | 0.60 × 0.52 × 0.24 mm |
| Oxford Diffraction Xcalibur diffractometer with Sapphire CCD Detector | 2072 independent reflections |
| Radiation source: fine-focus sealed tube | 1614 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.022 |
| T = 299(2) K | θmax = 26.4º |
| Rotation method data acquisition using ω and φ scans. | θmin = 3.0º |
| Absorption correction: multi-scan (SCALE3 ABSPACK; Oxford Diffraction, 2007) | h = −12→11 |
| Tmin = 0.706, Tmax = 0.865 | k = −11→13 |
| 11267 measured reflections | l = −24→20 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.032 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.098 | w = 1/[σ2(Fo2) + (0.0385P)2 + 1.4567P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.10 | (Δ/σ)max = 0.044 |
| 2072 reflections | Δρmax = 0.35 e Å−3 |
| 155 parameters | Δρmin = −0.36 e Å−3 |
| 1 restraint | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0230 (13) |
| C8H6Cl2N2O3 | V = 2033.0 (2) Å3 |
| Mr = 249.05 | Z = 8 |
| Orthorhombic, Pbca | Mo Kα |
| a = 9.6092 (6) Å | µ = 0.63 mm−1 |
| b = 10.6487 (7) Å | T = 299 (2) K |
| c = 19.868 (1) Å | 0.60 × 0.52 × 0.24 mm |
| Oxford Diffraction Xcalibur diffractometer with Sapphire CCD Detector | 2072 independent reflections |
| Absorption correction: multi-scan (SCALE3 ABSPACK; Oxford Diffraction, 2007) | 1614 reflections with I > 2σ(I) |
| Tmin = 0.706, Tmax = 0.865 | Rint = 0.022 |
| 11267 measured reflections |
| R[F2 > 2σ(F2)] = 0.032 | 1 restraint |
| wR(F2) = 0.098 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.10 | Δρmax = 0.35 e Å−3 |
| 2072 reflections | Δρmin = −0.36 e Å−3 |
| 155 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 | ||
| C1 | 0.03253 (19) | 0.14098 (18) | 0.60262 (10) | 0.0344 (4) | |
| C2 | 0.1408 (2) | 0.05696 (19) | 0.61012 (11) | 0.0365 (4) | |
| H2 | 0.204 (2) | 0.043 (2) | 0.5757 (12) | 0.044* | |
| C3 | 0.1543 (2) | −0.00244 (19) | 0.67144 (11) | 0.0380 (5) | |
| C4 | 0.0653 (2) | 0.0166 (2) | 0.72466 (11) | 0.0453 (5) | |
| H4 | 0.075 (3) | −0.025 (2) | 0.7632 (14) | 0.054* | |
| C5 | −0.0418 (2) | 0.1009 (2) | 0.71576 (12) | 0.0490 (6) | |
| H5 | −0.103 (3) | 0.122 (2) | 0.7521 (14) | 0.059* | |
| C6 | −0.0584 (2) | 0.1632 (2) | 0.65542 (11) | 0.0426 (5) | |
| H6 | −0.131 (3) | 0.220 (2) | 0.6503 (13) | 0.051* | |
| C7 | 0.1102 (2) | 0.24984 (19) | 0.50064 (11) | 0.0357 (4) | |
| C8 | 0.0552 (2) | 0.3297 (2) | 0.44287 (11) | 0.0398 (5) | |
| H8 | −0.034 (3) | 0.352 (2) | 0.4488 (11) | 0.048* | |
| N1 | 0.01034 (17) | 0.20745 (17) | 0.54149 (9) | 0.0381 (4) | |
| H1N | −0.0711 (18) | 0.227 (2) | 0.5320 (12) | 0.046* | |
| N2 | 0.2700 (2) | −0.09083 (18) | 0.67926 (10) | 0.0491 (5) | |
| O1 | 0.23372 (15) | 0.22854 (16) | 0.50684 (9) | 0.0532 (5) | |
| O2 | 0.3669 (2) | −0.08426 (19) | 0.63930 (10) | 0.0664 (5) | |
| O3 | 0.2672 (2) | −0.16436 (19) | 0.72637 (10) | 0.0759 (6) | |
| Cl1 | 0.15452 (6) | 0.46874 (5) | 0.43763 (3) | 0.0529 (2) | |
| Cl2 | 0.06927 (8) | 0.24208 (7) | 0.36778 (3) | 0.0661 (2) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0270 (9) | 0.0403 (10) | 0.0360 (10) | −0.0056 (8) | −0.0003 (8) | 0.0025 (8) |
| C2 | 0.0334 (10) | 0.0388 (10) | 0.0374 (10) | −0.0034 (8) | −0.0001 (8) | 0.0008 (8) |
| C3 | 0.0363 (10) | 0.0346 (10) | 0.0430 (11) | −0.0033 (8) | −0.0046 (9) | 0.0017 (8) |
| C4 | 0.0494 (13) | 0.0483 (12) | 0.0382 (11) | −0.0071 (10) | −0.0014 (10) | 0.0065 (10) |
| C5 | 0.0460 (13) | 0.0583 (14) | 0.0428 (12) | −0.0043 (11) | 0.0103 (10) | −0.0006 (10) |
| C6 | 0.0311 (10) | 0.0487 (12) | 0.0479 (12) | −0.0012 (9) | 0.0036 (9) | 0.0014 (10) |
| C7 | 0.0272 (9) | 0.0389 (10) | 0.0409 (10) | 0.0013 (8) | −0.0009 (8) | 0.0020 (8) |
| C8 | 0.0307 (10) | 0.0479 (12) | 0.0409 (11) | 0.0006 (9) | −0.0001 (9) | 0.0045 (9) |
| N1 | 0.0239 (8) | 0.0503 (10) | 0.0401 (9) | 0.0018 (7) | −0.0002 (7) | 0.0076 (8) |
| N2 | 0.0507 (11) | 0.0446 (10) | 0.0521 (11) | 0.0028 (9) | −0.0091 (10) | 0.0056 (9) |
| O1 | 0.0258 (7) | 0.0698 (11) | 0.0641 (10) | 0.0050 (7) | 0.0044 (7) | 0.0272 (8) |
| O2 | 0.0606 (11) | 0.0718 (12) | 0.0668 (12) | 0.0250 (10) | 0.0086 (10) | 0.0109 (10) |
| O3 | 0.0786 (13) | 0.0713 (12) | 0.0778 (13) | 0.0122 (11) | −0.0056 (11) | 0.0361 (11) |
| Cl1 | 0.0558 (4) | 0.0395 (3) | 0.0635 (4) | −0.0031 (2) | −0.0001 (3) | 0.0064 (2) |
| Cl2 | 0.0740 (5) | 0.0778 (5) | 0.0467 (4) | −0.0200 (4) | −0.0084 (3) | −0.0116 (3) |
| C1—C2 | 1.380 (3) | C6—H6 | 0.93 (3) |
| C1—C6 | 1.386 (3) | C7—O1 | 1.215 (2) |
| C1—N1 | 1.422 (2) | C7—N1 | 1.335 (3) |
| C2—C3 | 1.379 (3) | C7—C8 | 1.523 (3) |
| C2—H2 | 0.93 (2) | C8—Cl1 | 1.764 (2) |
| C3—C4 | 1.376 (3) | C8—Cl2 | 1.765 (2) |
| C3—N2 | 1.464 (3) | C8—H8 | 0.90 (3) |
| C4—C5 | 1.377 (3) | N1—H1N | 0.833 (16) |
| C4—H4 | 0.89 (3) | N2—O3 | 1.220 (3) |
| C5—C6 | 1.380 (3) | N2—O2 | 1.226 (3) |
| C5—H5 | 0.96 (3) | ||
| C2—C1—C6 | 120.30 (19) | C1—C6—H6 | 120.0 (16) |
| C2—C1—N1 | 121.86 (17) | O1—C7—N1 | 125.26 (19) |
| C6—C1—N1 | 117.83 (18) | O1—C7—C8 | 121.32 (19) |
| C3—C2—C1 | 117.65 (19) | N1—C7—C8 | 113.42 (17) |
| C3—C2—H2 | 120.9 (15) | C7—C8—Cl1 | 108.99 (14) |
| C1—C2—H2 | 121.5 (15) | C7—C8—Cl2 | 108.35 (15) |
| C4—C3—C2 | 123.5 (2) | Cl1—C8—Cl2 | 110.62 (12) |
| C4—C3—N2 | 119.03 (19) | C7—C8—H8 | 112.2 (15) |
| C2—C3—N2 | 117.42 (19) | Cl1—C8—H8 | 107.9 (16) |
| C3—C4—C5 | 117.6 (2) | Cl2—C8—H8 | 108.8 (15) |
| C3—C4—H4 | 121.6 (17) | C7—N1—C1 | 125.44 (17) |
| C5—C4—H4 | 120.8 (17) | C7—N1—H1N | 116.8 (17) |
| C4—C5—C6 | 120.8 (2) | C1—N1—H1N | 117.5 (17) |
| C4—C5—H5 | 120.9 (16) | O3—N2—O2 | 123.4 (2) |
| C6—C5—H5 | 118.2 (16) | O3—N2—C3 | 118.5 (2) |
| C5—C6—C1 | 120.2 (2) | O2—N2—C3 | 118.10 (18) |
| C5—C6—H6 | 119.8 (16) | ||
| C6—C1—C2—C3 | −0.2 (3) | N1—C7—C8—Cl1 | 131.85 (17) |
| N1—C1—C2—C3 | 179.62 (18) | O1—C7—C8—Cl2 | 71.9 (2) |
| C1—C2—C3—C4 | 0.8 (3) | N1—C7—C8—Cl2 | −107.71 (18) |
| C1—C2—C3—N2 | −179.58 (18) | O1—C7—N1—C1 | 6.6 (4) |
| C2—C3—C4—C5 | −0.8 (3) | C8—C7—N1—C1 | −173.76 (18) |
| N2—C3—C4—C5 | 179.6 (2) | C2—C1—N1—C7 | −35.6 (3) |
| C3—C4—C5—C6 | 0.1 (3) | C6—C1—N1—C7 | 144.2 (2) |
| C4—C5—C6—C1 | 0.5 (3) | C4—C3—N2—O3 | 15.6 (3) |
| C2—C1—C6—C5 | −0.4 (3) | C2—C3—N2—O3 | −164.0 (2) |
| N1—C1—C6—C5 | 179.8 (2) | C4—C3—N2—O2 | −162.0 (2) |
| O1—C7—C8—Cl1 | −48.5 (3) | C2—C3—N2—O2 | 18.3 (3) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1N···O1i | 0.833 (16) | 2.081 (17) | 2.907 (2) | 171 (2) |
| Symmetry codes: (i) x−1/2, −y+1/2, −z+1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1N···O1i | 0.833 (16) | 2.081 (17) | 2.907 (2) | 171 (2) |
| Symmetry codes: (i) x−1/2, −y+1/2, −z+1. |
BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.
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As part of a study of the effect of ring and side chain substitutions on the solid state structures of acetanilides (Gowda et al., 2000, 2006, 2007), in the present work, the crystal structure of 2,2-dichloro-N- (3-nitrophenyl)-acetamide (3NPDCA) 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 in the structure of 3NPDCA (Fig.1) is anti to the meta nitro group, similar to that in the structure of 2-chloro-N-(3-nitrophenyl)-acetamide (3NPCA) (Gowda et al., 2007) and 2,2,2-trichloro-N-(3-nitrophenyl)-acetamide (3NPTCA)(Gowda et al., 2000) and meta chloro group in 2,2-dichloro-N-(3-chlorophenyl)-acetamide (3CPDCA)(Gowda et al., 2006). The geometric parameters in 3NPDCA are similar to those of 2,2-dichloro-N-(phenyl)-acetamide, 3CPDCA, 3NPCA, 3NPTCA and other acetanilides. The intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into chains running along the b axis (Fig. 2).