2,4-Dichloro-N-o-tolyl­benzamide

Aamer Saeed; Rasheed Ahmad Khera; Jim Simpson; Roderick G Stanley

doi:10.1107/S1600536809022752

. 2009 Jun 20;65(Pt 7):o1642. doi: 10.1107/S1600536809022752

2,4-Dichloro-N-o-tolylbenzamide

Aamer Saeed ^a,^*, Rasheed Ahmad Khera ^a, Jim Simpson ^b, Roderick G Stanley ^b

PMCID: PMC2969429 PMID: 21582906

Abstract

In the title compound, C₁₄H₁₁Cl₂NO, the central C—C(O)—N—C amide unit makes dihedral angles of 68.71 (11) and 54.92 (12)°, respectively, with the dichlorobenzene and tolyl rings. The two aromatic rings are inclined at 16.25 (17)°. In the crystal, N—H⋯O hydrogen bonds link molecules into zigzag chains propagating in [001]. C—H⋯Cl contacts link these chains and additional C—H⋯O contacts generate stacks down b. Weak C—H⋯π and C—Cl⋯π interactions [Cl⋯centroid distance = 3.5422 (15) Å] may also stabilize the structure.

Related literature

For the biological activity of benzamide derivatives, see: Saeed et al. (2008a ▶). For related structures, see: Gowda et al. (2008 ▶); Saeed et al. (2008b ▶); Zhou & Zheng (2007 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₄H₁₁Cl₂NO
M _r = 280.14
Monoclinic,
a = 22.517 (4) Å
b = 6.0405 (9) Å
c = 9.6332 (17) Å
β = 104.838 (9)°
V = 1266.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.50 mm⁻¹
T = 92 K
0.46 × 0.27 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T _min = 0.615, T _max = 0.91
9889 measured reflections
3475 independent reflections
3195 reflections with I > 2σ(I)
R _int = 0.043

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.158
S = 1.15
3475 reflections
164 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 1.36 e Å⁻³
Δρ_min = −0.62 e Å⁻³
Absolute structure: Flack (1983 ▶), 1248 Friedel pairs
Flack parameter: 0.05 (8)

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: APEX2 and SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and TITAN2000 (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 Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809022752/tk2478sup1.cif

e-65-o1642-sup1.cif^{(17.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022752/tk2478Isup2.hkl

e-65-o1642-Isup2.hkl^{(170.4KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.88	2.04	2.865 (4)	156
C6—H6⋯O1ⁱⁱ	0.95	2.55	3.415 (4)	151
C11—H11⋯Cl2ⁱⁱⁱ	0.95	2.83	3.680 (3)	150
C14—H14C⋯Cg2ⁱ	0.98	2.87	3.528 (4)	125

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) . Cg2 is the centroid of the C8–C13 ring.

Acknowledgments

We thank the University of Otago for purchase of the diffractometer.

supplementary crystallographic information

Comment

The biological activity and applications of benzamide derivatives have been described in an earlier paper (Saeed et al. 2008a). In the title compound, (I) & Fig. 1, the central C2–C1(O1)–N1–C8 amide unit makes dihedral angles of 68.71 (11) ° and 54.92 (12) ° with the C2···C7 and C8···C13 rings, respectively. The two aromatic rings are inclined at 16.25 (17)°. Bond distances within the molecule are normal (Allen et al. 1987) and similar to those observed in comparable structures (Gowda et al. 2008; Saeed et al. 2008b; Zhou & Zheng 2007). In the crystal, N1—H1···O1 hydrogen bonds link molecules into zig-zag chains down the c axis; Table 1 & Fig. 2. C11—H11···Cl2 contacts link these chains and additional C6—H6···O1 contacts generate three-dimensional stacks down b, Fig. 3. C14—H14···π and Cl1···π interactions (Cl···Cg1 distance 3.5422 (15) Å; Cg1 is the centroid of the C2···C7 ring) may also stabilize the structure.

Experimental

2,4-Dichlorobenzoyl chloride (5.4 mmol) in CHCl₃ was treated with 2-methylaniline (21.6 mmol) under a nitrogen atmosphere at reflux for 3 h. Upon cooling, the reaction mixture was diluted with CHCl₃ and washed consecutively with aq. 1 M HCl and saturated aq. NaHCO₃. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. Crystallization of the residue in CHCl₃ afforded (I) (81%) as colourless crystals: Anal. calcd. for C₁₄H₁₁Cl₂NO: C 60.02, H 3.96, N 5.00%; found: C 60.05, H 3.97, N 4.97%.