N-(2,6-Dichloro-phen-yl)-3-methyl-benzamide.

In the mol-ecular structure of the title compound, C(14)H(11)Cl(2)NO, the two aromatic rings form a dihedral angle of 70.9 (1)°. The central amido group -NH-C(=O)- makes a dihedral angle of 26.6 (2)° with the methyl-phenyl ring and 82.5 (1)° with the dichloro-phenyl ring. Inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into chains running along the c axis of the crystal.

Related literature

For the preparation of the title compound, see: Gowda et al. (2003 ▶). For related structures, see: Bowes et al. (2003 ▶); Gowda, Foro et al. (2008 ▶); Gowda, Tokarčík et al. (2008 ▶); Tokarčík et al., 2009 ▶).

Experimental

Crystal data

C14H11Cl2NO

M = 280.14

Monoclinic,

a = 11.9433 (8) Å

b = 12.5397 (6) Å

c = 9.5305 (5) Å

β = 111.859 (7)°

V = 1324.72 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.48 mm−1

T = 295 K

0.53 × 0.34 × 0.07 mm

Data collection

Oxford Diffraction Xcalibur2 diffractometer with a Sapphire CCD detector

Absorption correction: analytical (CrysAlis Pro; Oxford Diffraction, 2009 ▶) T min = 0.756, T max = 0.979

28271 measured reflections

2553 independent reflections

2368 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.068

S = 1.10

2553 reflections

164 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack (1983 ▶), 1273 Friedel pairs

Flack parameter: −0.02 (5)

Data collection: CrysAlis Pro (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; 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, PLATON (Spek, 2009 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809039889/bt5081sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039889/bt5081Isup2.hkl

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

C14H11Cl2NO	F(000) = 576
Mr = 280.14	Dx = 1.405 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 16815 reflections
a = 11.9433 (8) Å	θ = 2.9–29.5°
b = 12.5397 (6) Å	µ = 0.48 mm−1
c = 9.5305 (5) Å	T = 295 K
β = 111.859 (7)°	Block, colourless
V = 1324.72 (13) Å3	0.53 × 0.34 × 0.07 mm
Z = 4

Oxford Diffraction Xcalibur2 diffractometer with a Sapphire CCD detector	2553 independent reflections
graphite	2368 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1	Rint = 0.026
ω scans	θmax = 25.8°, θmin = 2.9°
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	h = −14→14
Tmin = 0.756, Tmax = 0.979	k = −15→15
28271 measured reflections	l = −11→11

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)] = 0.028	H-atom parameters constrained
wR(F2) = 0.068	w = 1/[σ2(Fo2) + (0.0314P)2 + 0.4349P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
2553 reflections	Δρmax = 0.18 e Å−3
164 parameters	Δρmin = −0.22 e Å−3
2 restraints	Absolute structure: Flack (1983), 1272 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.02 (5)

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
N1	0.47074 (14)	0.47784 (12)	0.42954 (16)	0.0406 (4)
H1N	0.4424	0.5119	0.4873	0.049*
C1	0.41176 (16)	0.48266 (14)	0.27880 (19)	0.0359 (4)
C2	0.30291 (15)	0.55238 (14)	0.22211 (19)	0.0370 (4)
C3	0.21557 (17)	0.52827 (16)	0.0820 (2)	0.0424 (4)
H3	0.226	0.469	0.0296	0.051*
C4	0.11285 (18)	0.59068 (19)	0.0182 (2)	0.0517 (5)
C5	0.1019 (2)	0.68018 (18)	0.0964 (3)	0.0579 (6)
H5	0.0352	0.7244	0.0541	0.069*
C6	0.1874 (2)	0.70552 (18)	0.2356 (2)	0.0569 (5)
H6	0.1774	0.7657	0.2868	0.068*
C7	0.28792 (18)	0.64175 (16)	0.2992 (2)	0.0452 (4)
H7	0.3454	0.6587	0.3935	0.054*
C8	0.57860 (17)	0.41798 (15)	0.49583 (19)	0.0376 (4)
C9	0.57762 (19)	0.31764 (15)	0.5562 (2)	0.0455 (4)
C10	0.6829 (2)	0.26073 (18)	0.6273 (3)	0.0598 (6)
H10	0.6806	0.1938	0.6682	0.072*
C11	0.7908 (2)	0.3044 (2)	0.6365 (2)	0.0624 (6)
H11	0.8621	0.2669	0.6848	0.075*
C12	0.79466 (19)	0.4020 (2)	0.5755 (2)	0.0564 (5)
H12	0.8679	0.4304	0.5801	0.068*
C13	0.68896 (18)	0.45856 (17)	0.5070 (2)	0.0449 (4)
C14	0.0183 (2)	0.5595 (3)	−0.1330 (3)	0.0798 (8)
H14A	−0.0283	0.5009	−0.1194	0.12*
H14B	0.0573	0.5387	−0.2006	0.12*
H14C	−0.0338	0.6191	−0.175	0.12*
O1	0.44576 (12)	0.43125 (11)	0.19225 (13)	0.0464 (3)
Cl1	0.44089 (6)	0.26275 (5)	0.54294 (8)	0.07568 (19)
Cl2	0.69514 (6)	0.58258 (5)	0.43069 (8)	0.0773 (2)

	U11	U22	U33	U12	U13	U23
N1	0.0406 (9)	0.0519 (9)	0.0281 (7)	0.0081 (7)	0.0116 (7)	0.0011 (7)
C1	0.0383 (9)	0.0381 (9)	0.0312 (8)	−0.0051 (7)	0.0128 (8)	−0.0003 (7)
C2	0.0382 (10)	0.0411 (9)	0.0307 (8)	−0.0045 (7)	0.0117 (7)	0.0038 (7)
C3	0.0436 (11)	0.0476 (11)	0.0342 (9)	−0.0031 (8)	0.0125 (8)	0.0028 (8)
C4	0.0399 (11)	0.0677 (14)	0.0398 (10)	−0.0049 (10)	0.0060 (9)	0.0083 (10)
C5	0.0473 (12)	0.0611 (13)	0.0610 (13)	0.0143 (10)	0.0152 (10)	0.0179 (11)
C6	0.0590 (13)	0.0513 (12)	0.0570 (13)	0.0061 (10)	0.0179 (11)	−0.0007 (10)
C7	0.0445 (11)	0.0470 (11)	0.0399 (10)	0.0008 (9)	0.0108 (8)	0.0001 (8)
C8	0.0415 (9)	0.0427 (9)	0.0269 (8)	0.0027 (7)	0.0106 (7)	−0.0029 (7)
C9	0.0526 (11)	0.0471 (10)	0.0384 (9)	−0.0004 (9)	0.0186 (8)	−0.0038 (9)
C10	0.0794 (17)	0.0476 (12)	0.0524 (13)	0.0205 (11)	0.0245 (12)	0.0091 (10)
C11	0.0597 (14)	0.0739 (16)	0.0461 (11)	0.0273 (12)	0.0111 (10)	0.0004 (11)
C12	0.0392 (11)	0.0774 (16)	0.0467 (11)	0.0039 (10)	0.0092 (9)	−0.0051 (11)
C13	0.0457 (11)	0.0504 (11)	0.0351 (9)	−0.0034 (9)	0.0109 (8)	−0.0042 (8)
C14	0.0539 (15)	0.117 (2)	0.0508 (14)	0.0038 (15)	−0.0015 (11)	0.0086 (14)
O1	0.0515 (8)	0.0573 (8)	0.0298 (6)	0.0054 (6)	0.0146 (6)	−0.0021 (6)
Cl1	0.0755 (4)	0.0693 (4)	0.0878 (4)	−0.0162 (3)	0.0367 (3)	0.0088 (3)
Cl2	0.0730 (4)	0.0646 (4)	0.0919 (5)	−0.0154 (3)	0.0281 (3)	0.0157 (3)

N1—C1	1.345 (2)	C7—H7	0.93
N1—C8	1.420 (2)	C8—C13	1.380 (3)
N1—H1N	0.86	C8—C9	1.385 (3)
C1—O1	1.229 (2)	C9—C10	1.384 (3)
C1—C2	1.491 (3)	C9—Cl1	1.733 (2)
C2—C7	1.388 (3)	C10—C11	1.373 (4)
C2—C3	1.388 (3)	C10—H10	0.93
C3—C4	1.390 (3)	C11—C12	1.363 (4)
C3—H3	0.93	C11—H11	0.93
C4—C5	1.380 (3)	C12—C13	1.381 (3)
C4—C14	1.514 (3)	C12—H12	0.93
C5—C6	1.376 (3)	C13—Cl2	1.730 (2)
C5—H5	0.93	C14—H14A	0.96
C6—C7	1.381 (3)	C14—H14B	0.96
C6—H6	0.93	C14—H14C	0.96
C1—N1—C8	121.77 (15)	C13—C8—C9	117.29 (18)
C1—N1—H1N	119.1	C13—C8—N1	121.45 (18)
C8—N1—H1N	119.1	C9—C8—N1	121.23 (18)
O1—C1—N1	121.38 (17)	C10—C9—C8	121.7 (2)
O1—C1—C2	121.72 (15)	C10—C9—Cl1	119.38 (16)
N1—C1—C2	116.90 (15)	C8—C9—Cl1	118.94 (16)
C7—C2—C3	119.11 (16)	C11—C10—C9	119.1 (2)
C7—C2—C1	123.28 (15)	C11—C10—H10	120.5
C3—C2—C1	117.55 (16)	C9—C10—H10	120.5
C2—C3—C4	121.54 (18)	C12—C11—C10	120.7 (2)
C2—C3—H3	119.2	C12—C11—H11	119.6
C4—C3—H3	119.2	C10—C11—H11	119.6
C5—C4—C3	117.86 (18)	C11—C12—C13	119.5 (2)
C5—C4—C14	122.5 (2)	C11—C12—H12	120.3
C3—C4—C14	119.6 (2)	C13—C12—H12	120.3
C6—C5—C4	121.51 (19)	C8—C13—C12	121.7 (2)
C6—C5—H5	119.2	C8—C13—Cl2	119.23 (15)
C4—C5—H5	119.2	C12—C13—Cl2	119.04 (17)
C5—C6—C7	120.1 (2)	C4—C14—H14A	109.5
C5—C6—H6	120	C4—C14—H14B	109.5
C7—C6—H6	120	H14A—C14—H14B	109.5
C6—C7—C2	119.84 (17)	C4—C14—H14C	109.5
C6—C7—H7	120.1	H14A—C14—H14C	109.5
C2—C7—H7	120.1	H14B—C14—H14C	109.5
C8—N1—C1—O1	3.5 (3)	C1—N1—C8—C13	81.8 (2)
C8—N1—C1—C2	−177.04 (16)	C1—N1—C8—C9	−100.2 (2)
O1—C1—C2—C7	−152.45 (18)	C13—C8—C9—C10	1.1 (3)
N1—C1—C2—C7	28.1 (2)	N1—C8—C9—C10	−176.96 (17)
O1—C1—C2—C3	24.6 (2)	C13—C8—C9—Cl1	−179.28 (13)
N1—C1—C2—C3	−154.84 (16)	N1—C8—C9—Cl1	2.7 (2)
C7—C2—C3—C4	−0.9 (3)	C8—C9—C10—C11	−0.8 (3)
C1—C2—C3—C4	−178.08 (17)	Cl1—C9—C10—C11	179.57 (17)
C2—C3—C4—C5	2.1 (3)	C9—C10—C11—C12	−0.5 (3)
C2—C3—C4—C14	−178.3 (2)	C10—C11—C12—C13	1.5 (3)
C3—C4—C5—C6	−2.2 (3)	C9—C8—C13—C12	−0.1 (3)
C14—C4—C5—C6	178.3 (2)	N1—C8—C13—C12	177.97 (17)
C4—C5—C6—C7	1.0 (4)	C9—C8—C13—Cl2	178.92 (14)
C5—C6—C7—C2	0.4 (3)	N1—C8—C13—Cl2	−3.0 (2)
C3—C2—C7—C6	−0.4 (3)	C11—C12—C13—C8	−1.2 (3)
C1—C2—C7—C6	176.62 (18)	C11—C12—C13—Cl2	179.77 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.86	2.07	2.866 (2)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.86	2.07	2.866 (2)	155

Symmetry code: (i) .