Acta Cryst. (2008). E64, o987 [ doi:10.1107/S160053680801266X ]
In the title compound, C8H8ClNO, the conformations of the N-H and C=O bonds are anti to each other, but the C-Cl and C=O bonds in the side chain are syn. The molecules are linked by N-H
O hydrogen bonds into infinite chains running in the [101] direction.
The title compound was prepared according to the literature method (Gowda et al., 2003) and colourless prisms of (I) were recrystallised from an ethanol solution.
The H atoms were placed in calculated positions (C-H = 0.93Å, N-H = 0.86Å) and refined as riding with Uiso(H) = 1.2Ueq(C,N).
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003) and WinGX (Farrugia, 1999).
![[Figure 1]](./hb2728fig1thm.gif)
| Fig. 1. Molecular structure of (I) with displacement ellipsoids for the non-hydrogen atoms drawn at the 50% probability level. |
![[Figure 2]](./hb2728fig2thm.gif)
| Fig. 2. Part of the packing for (I) viewed down the b axis showing the chains arising from N-H···O hydrogen bonds Symmetry code (i): x - 1/2,-y + 1/2,z - 1/2. |
| C8H8ClNO | F000 = 352 |
| Mr = 169.6 | Dx = 1.36 Mg m−3 |
| Monoclinic, Cc | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: C -2yc | Cell parameters from 159 reflections |
| a = 5.0623 (15) Å | θ = 4.9–25.1º |
| b = 18.361 (6) Å | µ = 0.40 mm−1 |
| c = 9.115 (2) Å | T = 297 (2) K |
| β = 102.13 (3)º | Prism, colorless |
| V = 828.3 (4) Å3 | 0.41 × 0.24 × 0.17 mm |
| Z = 4 |
| Oxford Diffraction Xcalibur System diffractometer | 1067 independent reflections |
| Radiation source: Enhance (Mo) X-ray Source | 385 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.046 |
| Detector resolution: 10.4340 pixels mm-1 | θmax = 26º |
| T = 297(2) K | θmin = 4.3º |
| ω scans | h = −6→6 |
| Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2006), using a multifaceted crystal model based on expressions derived by Clark & Reid (1995)] | k = −22→22 |
| Tmin = 0.905, Tmax = 0.938 | l = −9→11 |
| 2388 measured reflections |
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.036 |
[exp(3.70(sinθ/λ)2)]/[σ2(Fo2) + (0.035P)2]
where P = 0.33333Fo2 + 0.66667Fc2 |
| wR(F2) = 0.086 | (Δ/σ)max < 0.001 |
| S = 0.96 | Δρmax = 0.1 e Å−3 |
| 1067 reflections | Δρmin = −0.11 e Å−3 |
| 106 parameters | Extinction correction: none |
| 2 restraints | Absolute structure: Flack (1983), 254 Friedel pairs |
| Primary atom site location: structure-invariant direct methods | Flack parameter: 0.04 (11) |
| Secondary atom site location: difference Fourier map |
| C8H8ClNO | V = 828.3 (4) Å3 |
| Mr = 169.6 | Z = 4 |
| Monoclinic, Cc | Mo Kα |
| a = 5.0623 (15) Å | µ = 0.40 mm−1 |
| b = 18.361 (6) Å | T = 297 (2) K |
| c = 9.115 (2) Å | 0.41 × 0.24 × 0.17 mm |
| β = 102.13 (3)º |
| Oxford Diffraction Xcalibur System diffractometer | 1067 independent reflections |
| Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2006), using a multifaceted crystal model based on expressions derived by Clark & Reid (1995)] | 385 reflections with I > 2σ(I) |
| Tmin = 0.905, Tmax = 0.938 | Rint = 0.046 |
| 2388 measured reflections |
| R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
| wR(F2) = 0.086 | Δρmax = 0.1 e Å−3 |
| S = 0.96 | Δρmin = −0.11 e Å−3 |
| 1067 reflections | Absolute structure: Flack (1983), 254 Friedel pairs |
| 106 parameters | Flack parameter: 0.04 (11) |
| 2 restraints |
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 | ||
| Cl1 | 1.3492 (4) | 0.15000 (9) | 0.9151 (2) | 0.1082 (7) | |
| C1 | 1.0871 (11) | 0.1998 (3) | 0.8076 (6) | 0.0824 (18) | |
| H1A | 1.1488 | 0.2215 | 0.7237 | 0.099* | |
| H1B | 0.939 | 0.1671 | 0.7672 | 0.099* | |
| C2 | 0.9849 (11) | 0.2595 (3) | 0.8961 (6) | 0.0629 (17) | |
| N1 | 0.7939 (8) | 0.3008 (2) | 0.8086 (4) | 0.0642 (13) | |
| H1N | 0.7565 | 0.2897 | 0.7149 | 0.077* | |
| O1 | 1.0653 (7) | 0.26846 (19) | 1.0314 (3) | 0.0833 (13) | |
| C3 | 0.6481 (10) | 0.3597 (3) | 0.8507 (6) | 0.0517 (13) | |
| C4 | 0.7302 (11) | 0.3975 (3) | 0.9862 (6) | 0.0670 (17) | |
| H4 | 0.888 | 0.3845 | 1.0536 | 0.08* | |
| C5 | 0.5727 (15) | 0.4542 (3) | 1.0177 (7) | 0.082 (2) | |
| H5 | 0.6222 | 0.478 | 1.1094 | 0.099* | |
| C6 | 0.3490 (16) | 0.4762 (3) | 0.9197 (10) | 0.0824 (18) | |
| H6 | 0.2513 | 0.516 | 0.9428 | 0.099* | |
| C7 | 0.2640 (13) | 0.4399 (4) | 0.7850 (7) | 0.082 (2) | |
| H7 | 0.1068 | 0.4538 | 0.7183 | 0.099* | |
| C8 | 0.4153 (10) | 0.3835 (4) | 0.7525 (6) | 0.0676 (16) | |
| H8 | 0.3614 | 0.3598 | 0.6609 | 0.081* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.1120 (13) | 0.1207 (13) | 0.0829 (10) | 0.0402 (13) | −0.0004 (9) | 0.0083 (13) |
| C1 | 0.079 (4) | 0.091 (4) | 0.067 (4) | 0.022 (4) | −0.006 (3) | 0.006 (4) |
| C2 | 0.070 (4) | 0.071 (4) | 0.045 (3) | −0.003 (3) | 0.005 (3) | 0.004 (4) |
| N1 | 0.066 (3) | 0.084 (3) | 0.035 (3) | 0.012 (3) | −0.006 (2) | 0.003 (3) |
| O1 | 0.102 (3) | 0.097 (3) | 0.039 (2) | 0.010 (2) | −0.013 (2) | −0.005 (2) |
| C3 | 0.051 (4) | 0.062 (4) | 0.041 (3) | −0.001 (3) | 0.008 (3) | 0.002 (3) |
| C4 | 0.055 (4) | 0.084 (4) | 0.059 (4) | 0.005 (4) | 0.007 (3) | −0.004 (3) |
| C5 | 0.083 (5) | 0.097 (5) | 0.073 (5) | −0.005 (5) | 0.029 (4) | −0.014 (4) |
| C6 | 0.078 (5) | 0.071 (4) | 0.101 (5) | 0.002 (5) | 0.027 (4) | 0.005 (5) |
| C7 | 0.066 (5) | 0.094 (5) | 0.081 (5) | 0.019 (5) | 0.005 (4) | 0.020 (5) |
| C8 | 0.053 (4) | 0.090 (5) | 0.058 (4) | 0.003 (3) | 0.006 (3) | 0.014 (3) |
| Cl1—C1 | 1.735 (5) | C4—C5 | 1.378 (7) |
| C1—C2 | 1.515 (6) | C4—H4 | 0.93 |
| C1—H1A | 0.97 | C5—C6 | 1.349 (8) |
| C1—H1B | 0.97 | C5—H5 | 0.93 |
| C2—O1 | 1.226 (6) | C6—C7 | 1.384 (9) |
| C2—N1 | 1.350 (6) | C6—H6 | 0.93 |
| N1—C3 | 1.407 (6) | C7—C8 | 1.357 (7) |
| N1—H1N | 0.86 | C7—H7 | 0.93 |
| C3—C8 | 1.392 (6) | C8—H8 | 0.93 |
| C3—C4 | 1.401 (7) | ||
| C2—C1—Cl1 | 112.8 (4) | C5—C4—C3 | 118.7 (6) |
| C2—C1—H1A | 109 | C5—C4—H4 | 120.7 |
| Cl1—C1—H1A | 109 | C3—C4—H4 | 120.7 |
| C2—C1—H1B | 109 | C6—C5—C4 | 122.0 (6) |
| Cl1—C1—H1B | 109 | C6—C5—H5 | 119 |
| H1A—C1—H1B | 107.8 | C4—C5—H5 | 119 |
| O1—C2—N1 | 124.3 (6) | C5—C6—C7 | 120.3 (6) |
| O1—C2—C1 | 123.7 (6) | C5—C6—H6 | 119.8 |
| N1—C2—C1 | 112.0 (5) | C7—C6—H6 | 119.8 |
| C2—N1—C3 | 128.5 (5) | C8—C7—C6 | 118.5 (6) |
| C2—N1—H1N | 115.7 | C8—C7—H7 | 120.8 |
| C3—N1—H1N | 115.7 | C6—C7—H7 | 120.8 |
| C8—C3—C4 | 117.8 (5) | C7—C8—C3 | 122.6 (6) |
| C8—C3—N1 | 119.2 (5) | C7—C8—H8 | 118.7 |
| C4—C3—N1 | 123.0 (5) | C3—C8—H8 | 118.7 |
| Cl1—C1—C2—O1 | −4.8 (7) | N1—C3—C4—C5 | −179.6 (5) |
| Cl1—C1—C2—N1 | 175.8 (4) | C3—C4—C5—C6 | −2.8 (9) |
| O1—C2—N1—C3 | −1.1 (9) | C4—C5—C6—C7 | 2.7 (9) |
| C1—C2—N1—C3 | 178.3 (5) | C5—C6—C7—C8 | −2.0 (9) |
| C2—N1—C3—C8 | −164.2 (5) | C6—C7—C8—C3 | 1.7 (8) |
| C2—N1—C3—C4 | 17.8 (8) | C4—C3—C8—C7 | −1.8 (8) |
| C8—C3—C4—C5 | 2.3 (8) | N1—C3—C8—C7 | −180.0 (5) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1N···O1i | 0.86 | 2.05 | 2.848 (5) | 155 |
| Symmetry codes: (i) x−1/2, −y+1/2, z−1/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1N···O1i | 0.86 | 2.05 | 2.848 (5) | 155 |
| Symmetry codes: (i) x−1/2, −y+1/2, z−1/2. |
BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for resumptions of his research fellowship. JK and MT thank the Grant Agency of the Slovak Republic (grant No. VEGA 1/0817/08) and the Structural Funds, Interreg IIIA, for financial support for the purchase of the diffractometer.
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In the present work, the structure of the title compoud, (I), 2-chloro-N-(phenyl)-acetamide (NPCA) has been determined, as part of a study of the effect of ring and side chain substitutions on the solid state geometry of aromatic amides (Gowda et al., 2007; 2008). The conformations of the N—H and C=O bonds are anti to each other, but the C—Cl and C=O bonds in the side chain are syn to each other (Fig. 1), similar to that observed in 2-chloro-N-(2-chlorophenyl)-acetamide (Gowda et al., 2007)and 2-chloro-N-(3-methylphenyl)-acetamide (Gowda et al., 2008) with similar bond parameters. Further, the amide group –NHCO– in (I) makes a dihedral angle of 16.0 (8)° with the phenyl ring.
Part of the packing for (I) viewed down the b axis is shown in Fig. 2. Infinite chains running along the base vector [101] are formed by N-H···O hydrogen bonds (Table 1).