2,4-Dichloro-N-p-tolyl­benzamide

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

doi:10.1107/S1600536809034710

. 2009 Sep 26;65(Pt 10):o2527. doi: 10.1107/S1600536809034710

2,4-Dichloro-N-p-tolylbenzamide

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

PMCID: PMC2970402 PMID: 21577972

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.

Related literature

For background to our work on benzamide derivatives, see: Saeed et al. (2008 ▶). For related structures see: Zhou & Zheng (2007 ▶); Gowda et al. (2008a ▶,b ▶,c ▶, 2009 ▶); Chopra & Guru Row (2005 ▶).

Experimental

Crystal data

C₁₄H₁₁Cl₂NO
M _r = 280.14
Monoclinic,
a = 9.0884 (18) Å
b = 9.825 (2) Å
c = 14.167 (3) Å
β = 94.208 (9)°
V = 1261.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.50 mm⁻¹
T = 89 K
0.33 × 0.26 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T _min = 0.753, T _max = 0.970
20982 measured reflections
4465 independent reflections
3463 reflections with I > 2σ(I)
R _int = 0.044

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.132
S = 1.15
4465 reflections
167 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.49 e Å⁻³

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/S1600536809034710/fl2252sup1.cif

e-65-o2527-sup1.cif^{(17KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034710/fl2252Isup2.hkl

e-65-o2527-Isup2.hkl^{(223.2KB, 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—H1N⋯O1ⁱ	0.86 (2)	2.14 (2)	2.9867 (17)	168 (2)
C12—H12⋯Cl1ⁱⁱ	0.95	2.91	3.7372 (17)	146
C6—H6⋯O1ⁱⁱⁱ	0.95	2.67	3.619 (2)	175
C7—H7⋯Cg2^iv	0.95	2.65	3.4865 (17)	147

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) . 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 background to our work on benzamide derivatives has been described in a previous paper (Saeed et al., 2008). In the title compound (I), Fig. 1, the C8–N1–C1(O1)–C2 amide unit is planar, r.m.s. deviation 0.0317 Å, and subtends dihedral angles of 65.93 (6)° and 29.45 (7)° respectively to the C2···C7 dichlorobenzene and C8···C13 tolyl rings. The two aromatic rings are inclined at 37.92 (6)° to one another. Bond distances within the molecule are normal and similar to those observed in comparable structures (Zhou & Zheng, 2007; Gowda et al. 2008a,b,c 2009; Chopra & Guru Row, 2005).

In the crystal structure N—H···O hydrogen bonds link molecules in a head to tail fashion into rows along b. C7—H7···π and weak, inversion related π–π contacts involving adjacent dichlorobenene rings [Cg···Cg distance 4.0217 (12), symmetry operation 1 - x, 1 - y, 1 - z] are also observed, Table 1, Fig 2. These together with additional C—H···Cl and C—H···O hydrogen bonds link the stacks of molecules alternately head to head and head to tail down the b axis, Fig. 3.

Experimental

2,4-Dichlorobenzoyl chloride (5.4 mmol) in CHCl₃ was treated with p-toluidine(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 magnesium sulfate and concentrated under reduced pressure. Crystallization of the residue by evaporation from CHCl₃ afforded the title compound (84%) as colourless needles: Anal. calcd. for C₁₄H₁₁Cl₂NO,: C, 60.02; H, 3.96; N, 5.00%; found: C, 60.06; H, 3.92; N, 5.10%