Abstract
In the title compound, C14H11Cl2NO, the C—N—C(=O)—C amide unit is almost planar (r.m.s. deviation = 0.0317 Å) and subtends dihedral angles of 65.93 (6) and 29.45 (7)°, respectively, to the dichlorobenzene and tolyl rings. The two aromatic rings are inclined at 37.92 (6)° to one another. In the crystal structure, N—H⋯O hydrogen bonds link the molecules into chains along b. Additional weak C—H⋯Cl and C—H⋯O hydrogen bonds combine with C—H⋯π and very weak π–π contacts [Cg⋯Cg distance = 4.0217 (12) Å] to stack the molecules down b.
Highlights
In the title compound, C14H11Cl2NO, the C—N—C( O)—C amide unit is almost planar (r.m.s. deviation = 0.0317 Å) and subtends dihedral angles of 65.93 (6) and 29.45 (7), respectively, to the dichlorobenzene and tolyl rings
Cg2 is the centroid of the C8–C13 ring
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+1, −y+1, −z+2; (iii) x, −y+3/2, z−1/2; (iv) x, −y+3/2, z+1/2
Summary
Key indicators: single-crystal X-ray study; T = 89 K; mean (C–C) = 0.002 Å; R factor =. 0.041; wR factor = 0.132; data-to-parameter ratio = 26.7. Cg2 is the centroid of the C8–C13 ring. N—H O hydrogen bonds link the molecules into chains along b. Additional weak C—H Cl and C—H O hydrogen bonds combine with C—H and very weak – contacts [Cg Cg distance = 4.0217 (12) Å] to stack the molecules down b. (Hunter & Simpson, 1999); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al, 2006); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004), PLATON (Spek, 2009) and publCIF (Westrip, 2009). Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FL2252)
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