2-Chloro-N-(2,6-dimethyl-phen-yl)benzamide.

In the title compound, C(15)H(14)ClNO, the dihedral angle between the benzoyl and the aniline rings is 3.30 (18)°. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into chains running along the a axis.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Bowes et al. (2003 ▶); Gowda et al. (2000 ▶, 2007 ▶, 2008 ▶); Saeed et al. (2010 ▶), on N-chloro­aryl­sulfonamides, see: Jyothi & Gowda (2004 ▶) and on N-bromo­aryl­sulfonamides, see: Usha & Gowda (2006 ▶).

Experimental

Crystal data

C15H14ClNO

M = 259.72

Monoclinic,

a = 4.8322 (3) Å

b = 12.7817 (10) Å

c = 21.8544 (12) Å

β = 90.778 (5)°

V = 1349.69 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 295 K

0.51 × 0.30 × 0.11 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009 ▶), based on expressions derived by Clark & Reid (1995 ▶)] T min = 0.907, T max = 0.971

18665 measured reflections

2469 independent reflections

1735 reflections with I > 2σ(I)

R int = 0.081

Refinement

R[F 2 > 2σ(F 2)] = 0.092

wR(F 2) = 0.248

S = 1.12

2469 reflections

168 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.50 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812015607/bt5865sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015607/bt5865Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812015607/bt5865Isup3.cml

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

C15H14ClNO	F(000) = 544
Mr = 259.72	Dx = 1.278 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3462 reflections
a = 4.8322 (3) Å	θ = 3.7–29.5°
b = 12.7817 (10) Å	µ = 0.27 mm−1
c = 21.8544 (12) Å	T = 295 K
β = 90.778 (5)°	Rod, colourless
V = 1349.69 (15) Å3	0.51 × 0.30 × 0.11 mm
Z = 4

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2469 independent reflections
Graphite monochromator	1735 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1	Rint = 0.081
ω scans	θmax = 25.3°, θmin = 4.2°
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]	h = −5→5
Tmin = 0.907, Tmax = 0.971	k = −15→15
18665 measured reflections	l = −26→26

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)] = 0.092	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.248	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ2(Fo2) + (0.080P)2 + 2.4052P] where P = (Fo2 + 2Fc2)/3
2469 reflections	(Δ/σ)max < 0.001
168 parameters	Δρmax = 0.50 e Å−3
1 restraint	Δρmin = −0.27 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	0.5223 (8)	0.2456 (4)	0.47475 (19)	0.0494 (10)
C2	0.3612 (11)	0.3360 (4)	0.4743 (2)	0.0660 (13)
C3	0.3033 (14)	0.3824 (5)	0.5300 (3)	0.0892 (19)
H3	0.1927	0.4419	0.5307	0.107*
C4	0.4038 (14)	0.3431 (5)	0.5834 (3)	0.094 (2)
H4	0.3632	0.3761	0.6202	0.113*
C5	0.5672 (11)	0.2539 (5)	0.5836 (2)	0.0720 (15)
H5	0.6349	0.2271	0.6204	0.086*
C6	0.6293 (9)	0.2050 (4)	0.5296 (2)	0.0528 (11)
C7	0.8109 (11)	0.1086 (4)	0.5297 (2)	0.0720 (15)
H7A	0.8096	0.0771	0.5696	0.108*
H7B	0.9967	0.1281	0.5197	0.108*
H7C	0.7417	0.0596	0.5	0.108*
C8	0.2532 (14)	0.3832 (4)	0.4152 (3)	0.0830 (17)
H8A	0.2349	0.4575	0.42	0.124*
H8B	0.0759	0.3534	0.4052	0.124*
H8C	0.3803	0.3685	0.3829	0.124*
C9	0.3874 (8)	0.1464 (3)	0.38474 (18)	0.0438 (10)
C10	0.4897 (8)	0.0847 (4)	0.3306 (2)	0.0533 (11)
C11	0.6640 (10)	0.0015 (4)	0.3394 (2)	0.0661 (13)
H11	0.7286	−0.0141	0.3786	0.079*
C12	0.7455 (13)	−0.0601 (5)	0.2903 (3)	0.0911 (19)
H12	0.8633	−0.1166	0.2968	0.109*
C13	0.6524 (15)	−0.0373 (6)	0.2326 (3)	0.097 (2)
H13	0.7055	−0.0789	0.1998	0.116*
C14	0.4789 (14)	0.0476 (6)	0.2226 (3)	0.0887 (19)
H14	0.4174	0.0643	0.1833	0.106*
C15	0.3997 (10)	0.1063 (4)	0.2718 (2)	0.0649 (13)
N1	0.5818 (7)	0.1927 (3)	0.41875 (15)	0.0460 (9)
H1	0.756 (4)	0.180 (4)	0.415 (2)	0.055*
O1	0.1424 (6)	0.1494 (3)	0.39531 (15)	0.0656 (10)
Cl1	0.1880 (4)	0.21406 (14)	0.25687 (7)	0.0994 (7)

	U11	U22	U33	U12	U13	U23
C1	0.050 (2)	0.053 (3)	0.045 (2)	0.0038 (19)	0.0043 (18)	−0.0021 (19)
C2	0.079 (3)	0.063 (3)	0.057 (3)	0.019 (3)	0.001 (2)	0.000 (2)
C3	0.119 (5)	0.076 (4)	0.073 (4)	0.039 (4)	0.007 (3)	−0.022 (3)
C4	0.127 (5)	0.096 (5)	0.061 (4)	0.029 (4)	0.013 (3)	−0.028 (3)
C5	0.086 (3)	0.089 (4)	0.041 (3)	0.002 (3)	−0.001 (2)	−0.006 (3)
C6	0.056 (2)	0.056 (3)	0.046 (2)	0.004 (2)	0.0018 (19)	−0.002 (2)
C7	0.079 (3)	0.082 (4)	0.055 (3)	0.018 (3)	−0.009 (2)	0.007 (3)
C8	0.118 (5)	0.065 (3)	0.066 (3)	0.033 (3)	−0.004 (3)	0.006 (3)
C9	0.041 (2)	0.052 (3)	0.039 (2)	0.0011 (18)	−0.0020 (16)	0.0078 (18)
C10	0.042 (2)	0.070 (3)	0.048 (2)	−0.005 (2)	0.0017 (18)	−0.005 (2)
C11	0.061 (3)	0.070 (3)	0.067 (3)	0.001 (3)	0.002 (2)	−0.016 (3)
C12	0.087 (4)	0.079 (4)	0.107 (5)	0.007 (3)	0.012 (4)	−0.036 (4)
C13	0.110 (5)	0.108 (5)	0.073 (4)	−0.019 (4)	0.020 (4)	−0.046 (4)
C14	0.101 (4)	0.112 (5)	0.053 (3)	−0.019 (4)	0.000 (3)	−0.019 (3)
C15	0.068 (3)	0.074 (3)	0.052 (3)	−0.012 (3)	0.004 (2)	−0.003 (2)
N1	0.0393 (17)	0.056 (2)	0.0428 (19)	0.0052 (16)	0.0047 (15)	−0.0015 (16)
O1	0.0413 (17)	0.093 (3)	0.062 (2)	0.0015 (16)	0.0020 (14)	−0.0100 (18)
Cl1	0.1313 (14)	0.1054 (13)	0.0612 (9)	0.0210 (10)	−0.0121 (8)	0.0189 (8)

C1—C2	1.394 (6)	C8—H8C	0.96
C1—C6	1.398 (6)	C9—O1	1.210 (5)
C1—N1	1.431 (5)	C9—N1	1.329 (5)
C2—C3	1.386 (7)	C9—C10	1.511 (6)
C2—C8	1.511 (7)	C10—C11	1.369 (7)
C3—C4	1.355 (9)	C10—C15	1.379 (7)
C3—H3	0.93	C11—C12	1.392 (8)
C4—C5	1.387 (8)	C11—H11	0.93
C4—H4	0.93	C12—C13	1.365 (10)
C5—C6	1.373 (7)	C12—H12	0.93
C5—H5	0.93	C13—C14	1.387 (9)
C6—C7	1.512 (7)	C13—H13	0.93
C7—H7A	0.96	C14—C15	1.370 (8)
C7—H7B	0.96	C14—H14	0.93
C7—H7C	0.96	C15—Cl1	1.744 (6)
C8—H8A	0.96	N1—H1	0.860 (19)
C8—H8B	0.96
C2—C1—C6	120.9 (4)	C2—C8—H8C	109.5
C2—C1—N1	120.3 (4)	H8A—C8—H8C	109.5
C6—C1—N1	118.8 (4)	H8B—C8—H8C	109.5
C3—C2—C1	117.9 (5)	O1—C9—N1	124.4 (4)
C3—C2—C8	120.6 (5)	O1—C9—C10	119.8 (4)
C1—C2—C8	121.5 (4)	N1—C9—C10	115.7 (3)
C4—C3—C2	121.6 (5)	C11—C10—C15	118.2 (5)
C4—C3—H3	119.2	C11—C10—C9	120.2 (4)
C2—C3—H3	119.2	C15—C10—C9	121.6 (4)
C3—C4—C5	120.2 (5)	C10—C11—C12	120.7 (6)
C3—C4—H4	119.9	C10—C11—H11	119.6
C5—C4—H4	119.9	C12—C11—H11	119.6
C6—C5—C4	120.3 (5)	C13—C12—C11	119.9 (6)
C6—C5—H5	119.9	C13—C12—H12	120
C4—C5—H5	119.9	C11—C12—H12	120
C5—C6—C1	119.0 (4)	C12—C13—C14	120.2 (6)
C5—C6—C7	120.2 (4)	C12—C13—H13	119.9
C1—C6—C7	120.8 (4)	C14—C13—H13	119.9
C6—C7—H7A	109.5	C15—C14—C13	118.7 (6)
C6—C7—H7B	109.5	C15—C14—H14	120.7
H7A—C7—H7B	109.5	C13—C14—H14	120.7
C6—C7—H7C	109.5	C14—C15—C10	122.3 (6)
H7A—C7—H7C	109.5	C14—C15—Cl1	117.1 (5)
H7B—C7—H7C	109.5	C10—C15—Cl1	120.6 (4)
C2—C8—H8A	109.5	C9—N1—C1	122.7 (3)
C2—C8—H8B	109.5	C9—N1—H1	124 (3)
H8A—C8—H8B	109.5	C1—N1—H1	112 (3)
C6—C1—C2—C3	−2.0 (8)	N1—C9—C10—C15	−122.9 (5)
N1—C1—C2—C3	178.2 (5)	C15—C10—C11—C12	−0.6 (7)
C6—C1—C2—C8	177.6 (5)	C9—C10—C11—C12	175.8 (5)
N1—C1—C2—C8	−2.2 (8)	C10—C11—C12—C13	0.3 (9)
C1—C2—C3—C4	1.4 (10)	C11—C12—C13—C14	0.6 (10)
C8—C2—C3—C4	−178.2 (7)	C12—C13—C14—C15	−1.2 (10)
C2—C3—C4—C5	−0.6 (11)	C13—C14—C15—C10	0.9 (9)
C3—C4—C5—C6	0.3 (10)	C13—C14—C15—Cl1	178.6 (5)
C4—C5—C6—C1	−0.9 (8)	C11—C10—C15—C14	0.0 (7)
C4—C5—C6—C7	179.1 (5)	C9—C10—C15—C14	−176.4 (5)
C2—C1—C6—C5	1.8 (7)	C11—C10—C15—Cl1	−177.6 (4)
N1—C1—C6—C5	−178.4 (4)	C9—C10—C15—Cl1	6.0 (6)
C2—C1—C6—C7	−178.2 (5)	O1—C9—N1—C1	4.6 (7)
N1—C1—C6—C7	1.6 (7)	C10—C9—N1—C1	−173.9 (4)
O1—C9—C10—C11	−117.8 (5)	C2—C1—N1—C9	−65.8 (6)
N1—C9—C10—C11	60.8 (6)	C6—C1—N1—C9	114.4 (5)
O1—C9—C10—C15	58.5 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86 (2)	1.96 (2)	2.818 (4)	172 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86 (2)	1.96 (2)	2.818 (4)	172 (4)

Symmetry code: (i) .