N-(2,6-Dichloro-phen-yl)-4-methyl-benzamide.

In the title compound, C(14)H(11)Cl(2)NO, the two aromatic rings are nearly orthogonal to each other [dihedral angle 79.7 (1)°], while the central amide core -NH-C(=O)- is nearly coplanar with the benzoyl ring [N-C-C-C torsion angles = -5.5 (3) and 1772. (2)°]. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into C(4) chains propagating in [001].

Related literature

For our studies on the effects of substituents on the structures of N-(ar­yl)-amides, see: Bhat & Gowda (2000 ▶); Gowda et al. (2006 ▶, 2009 ▶), on N-(ar­yl)-methane­sulfonamides, see: Jayalakshmi & Gowda (2004 ▶) and on N-(ar­yl)-aryl­sulfonamides, see: Gowda et al. (2005 ▶).

Experimental

Crystal data

C14H11Cl2NO

M = 280.14

Tetragonal,

a = 16.4706 (8) Å

c = 19.8709 (9) Å

V = 5390.6 (4) Å3

Z = 16

Mo Kα radiation

μ = 0.47 mm−1

T = 293 K

0.48 × 0.34 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.807, T max = 0.937

5852 measured reflections

2752 independent reflections

1701 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.120

S = 1.01

2752 reflections

166 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811028935/bt6816sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028935/bt6816Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811028935/bt6816Isup3.cml

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

C14H11Cl2NO	Dx = 1.381 Mg m−3
Mr = 280.14	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/a	Cell parameters from 1773 reflections
Hall symbol: -I 4ad	θ = 2.8–27.9°
a = 16.4706 (8) Å	µ = 0.47 mm−1
c = 19.8709 (9) Å	T = 293 K
V = 5390.6 (4) Å3	Prism, colourless
Z = 16	0.48 × 0.34 × 0.14 mm
F(000) = 2304

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2752 independent reflections
Radiation source: fine-focus sealed tube	1701 reflections with I > 2σ(I)
graphite	Rint = 0.021
Rotation method data acquisition using ω scans.	θmax = 26.4°, θmin = 3.0°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −12→17
Tmin = 0.807, Tmax = 0.937	k = −17→20
5852 measured reflections	l = −10→24

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0618P)2 + 1.1095P] where P = (Fo2 + 2Fc2)/3
2752 reflections	(Δ/σ)max = 0.001
166 parameters	Δρmax = 0.23 e Å−3
1 restraint	Δρmin = −0.21 e Å−3

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
C1	0.14058 (13)	0.52556 (15)	0.06376 (10)	0.0437 (5)
C2	0.07328 (15)	0.48135 (16)	0.08354 (12)	0.0542 (6)
C3	−0.00303 (16)	0.51539 (19)	0.08617 (14)	0.0686 (8)
H3	−0.0474	0.4849	0.1002	0.082*
C4	−0.01236 (17)	0.5952 (2)	0.06771 (14)	0.0707 (8)
H4	−0.0638	0.6186	0.0686	0.085*
C5	0.05259 (16)	0.64076 (17)	0.04806 (14)	0.0630 (7)
H5	0.0455	0.6947	0.0356	0.076*
C6	0.12874 (14)	0.60634 (16)	0.04678 (11)	0.0505 (6)
C7	0.25465 (13)	0.47064 (13)	0.00212 (10)	0.0397 (5)
C8	0.33829 (13)	0.43726 (13)	0.00489 (9)	0.0388 (5)
C9	0.37543 (16)	0.4135 (2)	−0.05361 (12)	0.0726 (9)
H9	0.3472	0.4172	−0.0940	0.087*
C10	0.45324 (17)	0.3845 (2)	−0.05353 (13)	0.0792 (9)
H10	0.4766	0.3692	−0.0942	0.095*
C11	0.49760 (14)	0.37724 (14)	0.00367 (12)	0.0497 (6)
C12	0.46104 (15)	0.40214 (18)	0.06207 (12)	0.0655 (8)
H12	0.4899	0.3992	0.1022	0.079*
C13	0.38295 (15)	0.43136 (17)	0.06293 (11)	0.0600 (7)
H13	0.3600	0.4474	0.1036	0.072*
C14	0.58324 (16)	0.34561 (19)	0.00401 (16)	0.0713 (8)
H14A	0.6167	0.3796	−0.0238	0.086*
H14B	0.5839	0.2912	−0.0132	0.086*
H14C	0.6038	0.3459	0.0492	0.086*
N1	0.21884 (11)	0.49001 (12)	0.06109 (8)	0.0462 (5)
H1N	0.2409 (14)	0.4795 (15)	0.0972 (9)	0.055*
O1	0.21852 (10)	0.48106 (11)	−0.05131 (7)	0.0548 (5)
Cl1	0.08438 (5)	0.37957 (5)	0.10321 (4)	0.0777 (3)
Cl2	0.21062 (4)	0.66582 (4)	0.02405 (4)	0.0717 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0379 (13)	0.0624 (16)	0.0309 (11)	0.0084 (11)	−0.0007 (9)	−0.0048 (10)
C2	0.0483 (15)	0.0640 (16)	0.0502 (14)	0.0043 (12)	−0.0027 (11)	0.0034 (11)
C3	0.0425 (15)	0.082 (2)	0.0817 (19)	0.0023 (14)	0.0067 (13)	0.0058 (15)
C4	0.0432 (16)	0.086 (2)	0.083 (2)	0.0163 (15)	0.0036 (14)	−0.0081 (16)
C5	0.0530 (16)	0.0590 (17)	0.0770 (18)	0.0150 (13)	−0.0009 (13)	−0.0057 (14)
C6	0.0438 (14)	0.0612 (16)	0.0465 (13)	0.0046 (11)	0.0013 (10)	−0.0056 (11)
C7	0.0430 (12)	0.0448 (13)	0.0315 (11)	0.0010 (10)	−0.0003 (9)	−0.0002 (9)
C8	0.0400 (12)	0.0426 (12)	0.0337 (11)	−0.0009 (10)	0.0014 (9)	−0.0010 (9)
C9	0.0600 (18)	0.120 (3)	0.0375 (13)	0.0260 (16)	−0.0047 (12)	−0.0161 (14)
C10	0.0616 (19)	0.127 (3)	0.0485 (15)	0.0296 (18)	0.0082 (14)	−0.0186 (16)
C11	0.0414 (13)	0.0509 (14)	0.0566 (14)	0.0011 (11)	0.0053 (11)	−0.0013 (11)
C12	0.0492 (16)	0.101 (2)	0.0461 (14)	0.0154 (14)	−0.0064 (12)	0.0001 (14)
C13	0.0492 (15)	0.095 (2)	0.0355 (13)	0.0157 (14)	0.0000 (11)	−0.0048 (12)
C14	0.0482 (16)	0.081 (2)	0.0845 (19)	0.0108 (14)	0.0077 (14)	−0.0042 (16)
N1	0.0414 (11)	0.0676 (14)	0.0297 (10)	0.0122 (9)	−0.0026 (8)	−0.0012 (9)
O1	0.0541 (10)	0.0812 (12)	0.0291 (8)	0.0129 (8)	−0.0065 (7)	−0.0015 (7)
Cl1	0.0697 (5)	0.0710 (5)	0.0924 (5)	0.0008 (4)	−0.0054 (4)	0.0200 (4)
Cl2	0.0594 (5)	0.0703 (5)	0.0853 (5)	−0.0040 (3)	0.0068 (3)	0.0012 (4)

C1—C2	1.383 (3)	C8—C9	1.371 (3)
C1—C6	1.386 (3)	C8—C13	1.371 (3)
C1—N1	1.417 (3)	C9—C10	1.368 (4)
C2—C3	1.377 (3)	C9—H9	0.9300
C2—Cl1	1.731 (3)	C10—C11	1.357 (3)
C3—C4	1.374 (4)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.370 (3)
C4—C5	1.364 (4)	C11—C14	1.504 (3)
C4—H4	0.9300	C12—C13	1.373 (3)
C5—C6	1.377 (3)	C12—H12	0.9300
C5—H5	0.9300	C13—H13	0.9300
C6—Cl2	1.727 (2)	C14—H14A	0.9600
C7—O1	1.229 (2)	C14—H14B	0.9600
C7—N1	1.350 (3)	C14—H14C	0.9600
C7—C8	1.484 (3)	N1—H1N	0.823 (16)
C2—C1—C6	117.5 (2)	C10—C9—C8	121.1 (2)
C2—C1—N1	121.5 (2)	C10—C9—H9	119.4
C6—C1—N1	121.0 (2)	C8—C9—H9	119.4
C3—C2—C1	121.9 (3)	C11—C10—C9	122.4 (2)
C3—C2—Cl1	118.8 (2)	C11—C10—H10	118.8
C1—C2—Cl1	119.30 (19)	C9—C10—H10	118.8
C4—C3—C2	118.8 (3)	C10—C11—C12	116.5 (2)
C4—C3—H3	120.6	C10—C11—C14	122.7 (2)
C2—C3—H3	120.6	C12—C11—C14	120.8 (2)
C5—C4—C3	121.0 (3)	C11—C12—C13	121.8 (2)
C5—C4—H4	119.5	C11—C12—H12	119.1
C3—C4—H4	119.5	C13—C12—H12	119.1
C4—C5—C6	119.6 (3)	C8—C13—C12	121.1 (2)
C4—C5—H5	120.2	C8—C13—H13	119.4
C6—C5—H5	120.2	C12—C13—H13	119.4
C5—C6—C1	121.3 (2)	C11—C14—H14A	109.5
C5—C6—Cl2	118.9 (2)	C11—C14—H14B	109.5
C1—C6—Cl2	119.88 (17)	H14A—C14—H14B	109.5
O1—C7—N1	120.3 (2)	C11—C14—H14C	109.5
O1—C7—C8	122.21 (18)	H14A—C14—H14C	109.5
N1—C7—C8	117.44 (17)	H14B—C14—H14C	109.5
C9—C8—C13	117.0 (2)	C7—N1—C1	121.85 (17)
C9—C8—C7	119.24 (19)	C7—N1—H1N	120.9 (17)
C13—C8—C7	123.73 (19)	C1—N1—H1N	117.2 (17)
C6—C1—C2—C3	0.3 (4)	O1—C7—C8—C13	174.2 (2)
N1—C1—C2—C3	−179.9 (2)	N1—C7—C8—C13	−5.5 (3)
C6—C1—C2—Cl1	178.38 (16)	C13—C8—C9—C10	0.7 (4)
N1—C1—C2—Cl1	−1.8 (3)	C7—C8—C9—C10	178.2 (3)
C1—C2—C3—C4	0.9 (4)	C8—C9—C10—C11	0.3 (5)
Cl1—C2—C3—C4	−177.2 (2)	C9—C10—C11—C12	−1.3 (5)
C2—C3—C4—C5	−1.0 (4)	C9—C10—C11—C14	−179.8 (3)
C3—C4—C5—C6	−0.1 (4)	C10—C11—C12—C13	1.3 (4)
C4—C5—C6—C1	1.4 (4)	C14—C11—C12—C13	179.9 (3)
C4—C5—C6—Cl2	−178.2 (2)	C9—C8—C13—C12	−0.6 (4)
C2—C1—C6—C5	−1.5 (3)	C7—C8—C13—C12	−178.0 (2)
N1—C1—C6—C5	178.7 (2)	C11—C12—C13—C8	−0.4 (4)
C2—C1—C6—Cl2	178.09 (17)	O1—C7—N1—C1	−2.5 (3)
N1—C1—C6—Cl2	−1.7 (3)	C8—C7—N1—C1	177.2 (2)
O1—C7—C8—C9	−3.2 (4)	C2—C1—N1—C7	105.8 (3)
N1—C7—C8—C9	177.2 (2)	C6—C1—N1—C7	−74.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.82 (2)	2.08 (2)	2.878 (2)	164 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.82 (2)	2.08 (2)	2.878 (2)	164 (2)

Symmetry code: (i) .