2,4-Dichloro-N-o-tolyl-benzamide.

In the title compound, C(14)H(11)Cl(2)NO, the central C-C(O)-N-C amide unit makes dihedral angles of 68.71 (11) and 54.92 (12)°, respectively, with the dichloro-benzene and tolyl rings. The two aromatic rings are inclined at 16.25 (17)°. In the crystal, N-H⋯O hydrogen bonds link mol-ecules 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 inter-actions [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 = 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

Δρmax = 1.36 e Å−3

Δρmin = −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 ▶).

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

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

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

C14H11Cl2NO	F(000) = 576
Mr = 280.14	Dx = 1.469 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 5253 reflections
a = 22.517 (4) Å	θ = 2.2–32.4°
b = 6.0405 (9) Å	µ = 0.50 mm−1
c = 9.6332 (17) Å	T = 92 K
β = 104.838 (9)°	Block, colourless
V = 1266.6 (4) Å3	0.46 × 0.27 × 0.19 mm
Z = 4

Bruker APEXII CCD diffractometer	3475 independent reflections
Radiation source: fine-focus sealed tube	3195 reflections with I > 2σ(I)
graphite	Rint = 0.043
ω scans	θmax = 33.1°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −34→33
Tmin = 0.615, Tmax = 0.91	k = −9→8
9889 measured reflections	l = −12→14

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)] = 0.057	H-atom parameters constrained
wR(F2) = 0.158	w = 1/[σ2(Fo2) + (0.0952P)2 + 1.0992P] where P = (Fo2 + 2Fc2)/3
S = 1.15	(Δ/σ)max < 0.001
3475 reflections	Δρmax = 1.36 e Å−3
164 parameters	Δρmin = −0.62 e Å−3
2 restraints	Absolute structure: Flack (1983), 1248 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.05 (8)

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
O1	0.16543 (13)	0.5847 (4)	0.3277 (3)	0.0250 (5)
C1	0.17020 (14)	0.5816 (5)	0.2022 (3)	0.0185 (5)
C2	0.22063 (13)	0.7094 (5)	0.1617 (3)	0.0172 (5)
C3	0.28213 (14)	0.6506 (5)	0.2168 (3)	0.0173 (5)
Cl1	0.30103 (4)	0.41955 (12)	0.32639 (7)	0.02356 (18)
C4	0.32950 (13)	0.7736 (5)	0.1848 (3)	0.0178 (5)
H4	0.3712	0.7311	0.2212	0.021*
C5	0.31386 (14)	0.9607 (5)	0.0978 (3)	0.0184 (5)
Cl2	0.37258 (4)	1.11763 (13)	0.06163 (7)	0.02513 (18)
C6	0.25310 (15)	1.0223 (5)	0.0405 (3)	0.0211 (5)
H6	0.2433	1.1492	−0.0192	0.025*
C7	0.20711 (15)	0.8956 (5)	0.0719 (3)	0.0202 (6)
H7	0.1654	0.9355	0.0319	0.024*
N1	0.13248 (12)	0.4699 (5)	0.0939 (3)	0.0197 (5)
H1	0.1365	0.4894	0.0063	0.024*
C8	0.08611 (13)	0.3210 (5)	0.1147 (3)	0.0191 (5)
C9	0.10239 (14)	0.1560 (5)	0.2194 (3)	0.0218 (6)
H9	0.1435	0.1458	0.2762	0.026*
C10	0.05858 (17)	0.0073 (6)	0.2407 (4)	0.0272 (7)
H10	0.0696	−0.1041	0.3123	0.033*
C11	−0.00132 (17)	0.0223 (6)	0.1568 (4)	0.0291 (7)
H11	−0.0316	−0.0780	0.1719	0.035*
C12	−0.01736 (15)	0.1832 (6)	0.0507 (4)	0.0261 (6)
H12	−0.0584	0.1889	−0.0075	0.031*
C13	0.02600 (14)	0.3385 (5)	0.0276 (3)	0.0203 (5)
C14	0.00831 (15)	0.5163 (6)	−0.0857 (4)	0.0261 (6)
H14A	0.0153	0.6622	−0.0401	0.039*
H14B	−0.0352	0.5007	−0.1358	0.039*
H14C	0.0333	0.5012	−0.1548	0.039*

	U11	U22	U33	U12	U13	U23
O1	0.0322 (12)	0.0350 (13)	0.0103 (10)	−0.0082 (9)	0.0100 (9)	−0.0035 (8)
C1	0.0219 (12)	0.0242 (13)	0.0107 (12)	−0.0017 (9)	0.0067 (10)	−0.0010 (9)
C2	0.0202 (11)	0.0246 (13)	0.0082 (10)	−0.0028 (9)	0.0060 (9)	−0.0016 (9)
C3	0.0242 (12)	0.0183 (11)	0.0107 (11)	−0.0014 (9)	0.0067 (9)	−0.0010 (9)
Cl1	0.0313 (4)	0.0213 (3)	0.0185 (3)	0.0008 (2)	0.0070 (3)	0.0049 (2)
C4	0.0207 (13)	0.0207 (12)	0.0125 (12)	−0.0008 (9)	0.0048 (10)	0.0008 (9)
C5	0.0230 (12)	0.0197 (11)	0.0139 (13)	−0.0038 (9)	0.0074 (10)	−0.0004 (9)
Cl2	0.0260 (3)	0.0289 (3)	0.0217 (4)	−0.0064 (3)	0.0084 (3)	0.0042 (3)
C6	0.0262 (13)	0.0243 (13)	0.0137 (12)	−0.0005 (10)	0.0068 (11)	0.0018 (10)
C7	0.0225 (13)	0.0270 (14)	0.0115 (13)	0.0012 (10)	0.0053 (10)	0.0014 (10)
N1	0.0225 (11)	0.0289 (12)	0.0092 (10)	−0.0043 (9)	0.0069 (9)	−0.0008 (9)
C8	0.0207 (12)	0.0266 (13)	0.0114 (12)	−0.0019 (10)	0.0067 (10)	−0.0032 (9)
C9	0.0256 (13)	0.0275 (14)	0.0141 (13)	0.0000 (11)	0.0085 (11)	0.0030 (11)
C10	0.0376 (17)	0.0237 (14)	0.0233 (16)	−0.0026 (12)	0.0134 (14)	0.0027 (11)
C11	0.0348 (17)	0.0288 (15)	0.0274 (18)	−0.0101 (13)	0.0149 (14)	−0.0045 (13)
C12	0.0236 (13)	0.0322 (16)	0.0231 (16)	−0.0039 (11)	0.0070 (12)	−0.0050 (13)
C13	0.0224 (13)	0.0261 (13)	0.0139 (13)	0.0008 (10)	0.0073 (10)	−0.0032 (10)
C14	0.0252 (14)	0.0351 (16)	0.0181 (15)	−0.0001 (12)	0.0060 (12)	0.0004 (12)

O1—C1	1.241 (4)	N1—H1	0.8800
C1—N1	1.346 (4)	C8—C9	1.399 (4)
C1—C2	1.505 (4)	C8—C13	1.402 (4)
C2—C3	1.396 (4)	C9—C10	1.388 (5)
C2—C7	1.404 (4)	C9—H9	0.9500
C3—C4	1.397 (4)	C10—C11	1.386 (5)
C3—Cl1	1.736 (3)	C10—H10	0.9500
C4—C5	1.398 (4)	C11—C12	1.389 (5)
C4—H4	0.9500	C11—H11	0.9500
C5—C6	1.388 (4)	C12—C13	1.412 (5)
C5—Cl2	1.733 (3)	C12—H12	0.9500
C6—C7	1.382 (5)	C13—C14	1.510 (5)
C6—H6	0.9500	C14—H14A	0.9800
C7—H7	0.9500	C14—H14B	0.9800
N1—C8	1.431 (4)	C14—H14C	0.9800
O1—C1—N1	124.6 (3)	C9—C8—C13	121.3 (3)
O1—C1—C2	120.3 (3)	C9—C8—N1	118.9 (3)
N1—C1—C2	115.1 (3)	C13—C8—N1	119.7 (3)
C3—C2—C7	118.4 (3)	C10—C9—C8	120.2 (3)
C3—C2—C1	120.8 (3)	C10—C9—H9	119.9
C7—C2—C1	120.8 (3)	C8—C9—H9	119.9
C2—C3—C4	121.3 (3)	C11—C10—C9	119.6 (3)
C2—C3—Cl1	120.0 (2)	C11—C10—H10	120.2
C4—C3—Cl1	118.7 (2)	C9—C10—H10	120.2
C3—C4—C5	118.2 (3)	C10—C11—C12	120.3 (3)
C3—C4—H4	120.9	C10—C11—H11	119.8
C5—C4—H4	120.9	C12—C11—H11	119.8
C6—C5—C4	121.8 (3)	C11—C12—C13	121.4 (3)
C6—C5—Cl2	119.9 (2)	C11—C12—H12	119.3
C4—C5—Cl2	118.3 (2)	C13—C12—H12	119.3
C7—C6—C5	118.8 (3)	C8—C13—C12	117.1 (3)
C7—C6—H6	120.6	C8—C13—C14	121.5 (3)
C5—C6—H6	120.6	C12—C13—C14	121.4 (3)
C6—C7—C2	121.5 (3)	C13—C14—H14A	109.5
C6—C7—H7	119.3	C13—C14—H14B	109.5
C2—C7—H7	119.3	H14A—C14—H14B	109.5
C1—N1—C8	123.1 (3)	C13—C14—H14C	109.5
C1—N1—H1	118.5	H14A—C14—H14C	109.5
C8—N1—H1	118.5	H14B—C14—H14C	109.5
O1—C1—C2—C3	66.1 (4)	C1—C2—C7—C6	176.2 (3)
N1—C1—C2—C3	−114.1 (3)	O1—C1—N1—C8	−7.1 (5)
O1—C1—C2—C7	−111.4 (4)	C2—C1—N1—C8	173.2 (3)
N1—C1—C2—C7	68.4 (4)	C1—N1—C8—C9	−50.9 (4)
C7—C2—C3—C4	0.3 (4)	C1—N1—C8—C13	130.9 (3)
C1—C2—C3—C4	−177.3 (3)	C13—C8—C9—C10	−1.0 (5)
C7—C2—C3—Cl1	−179.2 (2)	N1—C8—C9—C10	−179.1 (3)
C1—C2—C3—Cl1	3.2 (4)	C8—C9—C10—C11	0.4 (5)
C2—C3—C4—C5	1.2 (4)	C9—C10—C11—C12	0.8 (6)
Cl1—C3—C4—C5	−179.3 (2)	C10—C11—C12—C13	−1.6 (6)
C3—C4—C5—C6	−1.7 (5)	C9—C8—C13—C12	0.3 (5)
C3—C4—C5—Cl2	178.4 (2)	N1—C8—C13—C12	178.4 (3)
C4—C5—C6—C7	0.6 (5)	C9—C8—C13—C14	−180.0 (3)
Cl2—C5—C6—C7	−179.4 (2)	N1—C8—C13—C14	−1.8 (4)
C5—C6—C7—C2	1.0 (5)	C11—C12—C13—C8	1.0 (5)
C3—C2—C7—C6	−1.4 (5)	C11—C12—C13—C14	−178.8 (3)

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

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

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