2-Chloro-N-(2-methyl-phen-yl)benzamide.

In the title compound, C(14)H(12)ClNO, the two aromatic rings are almost coplanar, making a dihedral angle of 4.08 (18)°. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into infinite 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 ▶); Rodrigues et al. (2012 ▶); Saeed et al. (2010 ▶) of N-chloro­aryl­amides, see: Gowda & Rao (1989 ▶); Jyothi & Gowda (2004 ▶) and of N-bromo­aryl­sulfonamides, see: Gowda & Mahadevappa (1983 ▶); Usha & Gowda (2006 ▶).

Experimental

Crystal data

C14H12ClNO

M = 245.70

Orthorhombic,

a = 9.746 (3) Å

b = 6.077 (3) Å

c = 20.797 (7) Å

V = 1231.8 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 295 K

0.55 × 0.40 × 0.25 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 = 0.865, T max = 0.921

16249 measured reflections

2173 independent reflections

1369 reflections with I > 2σ(I)

R int = 0.097

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.147

S = 1.10

2173 reflections

158 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.14 e Å−3

Absolute structure: Flack (1983 ▶), 1054 Friedel pairs

Flack parameter: 0.37 (13)

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: DIAMOND (Brandenburg, 2002 ▶); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812023902/bt5935sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023902/bt5935Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812023902/bt5935Isup3.cml

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

C14H12ClNO	F(000) = 512
Mr = 245.70	Dx = 1.325 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2182 reflections
a = 9.746 (3) Å	θ = 3.5–25.0°
b = 6.077 (3) Å	µ = 0.29 mm−1
c = 20.797 (7) Å	T = 295 K
V = 1231.8 (8) Å3	Plate, colourless
Z = 4	0.55 × 0.40 × 0.25 mm

Xcalibur, Ruby, Gemini diffractometer	2173 independent reflections
Radiation source: fine-focus sealed tube	1369 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.097
Detector resolution: 10.434 pixels mm-1	θmax = 25.0°, θmin = 3.5°
ω scans	h = −11→11
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]	k = −7→7
Tmin = 0.865, Tmax = 0.921	l = −24→24
16249 measured reflections

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)] = 0.068	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.147	w = 1/[σ2(Fo2) + (0.058P)2] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
2173 reflections	Δρmax = 0.22 e Å−3
158 parameters	Δρmin = −0.14 e Å−3
2 restraints	Absolute structure: Flack (1983), 1054 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.37 (13)

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	0.5638 (4)	0.6837 (8)	0.4527 (3)	0.0506 (12)
C2	0.5037 (4)	0.5445 (10)	0.3997 (2)	0.0497 (14)
C3	0.5364 (4)	0.5696 (9)	0.3373 (3)	0.0596 (15)
C4	0.4845 (7)	0.4319 (12)	0.2916 (3)	0.0833 (19)
H4A	0.5099	0.4492	0.2488	0.100*
C5	0.3941 (6)	0.2667 (12)	0.3087 (5)	0.0850 (17)
H5A	0.3587	0.1723	0.2777	0.102*
C6	0.3578 (5)	0.2439 (10)	0.3713 (4)	0.0784 (17)
H6A	0.2968	0.1338	0.3834	0.094*
C7	0.4101 (4)	0.3811 (10)	0.4159 (3)	0.0644 (16)
H7A	0.3830	0.3660	0.4585	0.077*
C8	0.5196 (4)	0.9375 (9)	0.5395 (3)	0.0552 (14)
C9	0.4657 (5)	0.9069 (10)	0.6004 (3)	0.0646 (16)
C10	0.5118 (6)	1.0562 (13)	0.6480 (3)	0.0815 (18)
H10A	0.4756	1.0470	0.6893	0.098*
C11	0.6062 (7)	1.2098 (13)	0.6351 (4)	0.096 (3)
H11A	0.6403	1.2963	0.6684	0.115*
C12	0.6535 (5)	1.2420 (9)	0.5735 (4)	0.0813 (19)
H12A	0.7152	1.3549	0.5647	0.098*
C13	0.6101 (4)	1.1096 (10)	0.5260 (3)	0.0679 (17)
H13A	0.6402	1.1324	0.4841	0.082*
C14	0.3642 (5)	0.7289 (9)	0.6169 (3)	0.0664 (16)
H14C	0.3400	0.7395	0.6615	0.100*
H14B	0.4044	0.5875	0.6086	0.100*
H14A	0.2833	0.7461	0.5910	0.100*
N1	0.4759 (4)	0.7929 (8)	0.4882 (2)	0.0611 (12)
H1	0.3902 (14)	0.785 (9)	0.479 (3)	0.070 (17)*
O1	0.6897 (3)	0.6844 (6)	0.46020 (18)	0.0739 (11)
Cl1	0.64973 (16)	0.7710 (3)	0.31282 (10)	0.0971 (6)

	U11	U22	U33	U12	U13	U23
C1	0.042 (2)	0.046 (3)	0.063 (3)	0.001 (2)	−0.005 (2)	−0.001 (3)
C2	0.029 (2)	0.071 (4)	0.049 (3)	0.006 (2)	−0.002 (2)	−0.002 (2)
C3	0.044 (3)	0.076 (4)	0.059 (4)	0.006 (2)	0.000 (3)	−0.003 (3)
C4	0.088 (4)	0.102 (6)	0.060 (4)	0.024 (4)	−0.003 (3)	−0.011 (4)
C5	0.076 (4)	0.082 (4)	0.097 (5)	0.004 (3)	−0.012 (4)	−0.035 (4)
C6	0.064 (4)	0.078 (5)	0.093 (5)	−0.010 (3)	−0.004 (3)	−0.020 (4)
C7	0.042 (3)	0.081 (4)	0.070 (4)	−0.004 (2)	0.001 (2)	−0.004 (3)
C8	0.036 (2)	0.063 (4)	0.067 (4)	0.010 (3)	−0.011 (3)	−0.017 (3)
C9	0.054 (3)	0.074 (4)	0.066 (4)	0.020 (3)	−0.015 (3)	−0.011 (4)
C10	0.065 (3)	0.114 (6)	0.065 (4)	0.020 (4)	−0.002 (3)	−0.010 (4)
C11	0.090 (5)	0.104 (6)	0.094 (6)	0.015 (4)	−0.028 (4)	−0.049 (5)
C12	0.061 (3)	0.067 (4)	0.116 (6)	0.001 (3)	−0.015 (3)	−0.023 (4)
C13	0.046 (3)	0.077 (5)	0.080 (4)	0.002 (3)	−0.003 (3)	−0.006 (4)
C14	0.059 (3)	0.069 (4)	0.071 (4)	−0.001 (3)	−0.006 (2)	0.015 (3)
N1	0.039 (2)	0.082 (3)	0.062 (3)	0.002 (2)	−0.005 (2)	0.002 (3)
O1	0.0306 (15)	0.100 (3)	0.091 (2)	0.0024 (15)	−0.0065 (16)	−0.020 (2)
Cl1	0.0948 (11)	0.1063 (14)	0.0900 (10)	−0.0151 (10)	0.0021 (11)	0.0281 (10)

C1—O1	1.237 (5)	C8—C13	1.396 (7)
C1—N1	1.311 (6)	C8—N1	1.446 (6)
C1—C2	1.507 (7)	C9—C10	1.416 (8)
C2—C3	1.346 (6)	C9—C14	1.506 (8)
C2—C7	1.389 (7)	C10—C11	1.337 (10)
C3—C4	1.364 (7)	C10—H10A	0.9300
C3—Cl1	1.725 (6)	C11—C12	1.377 (10)
C4—C5	1.382 (9)	C11—H11A	0.9300
C4—H4A	0.9300	C12—C13	1.342 (8)
C5—C6	1.356 (11)	C12—H12A	0.9300
C5—H5A	0.9300	C13—H13A	0.9300
C6—C7	1.347 (8)	C14—H14C	0.9600
C6—H6A	0.9300	C14—H14B	0.9600
C7—H7A	0.9300	C14—H14A	0.9600
C8—C9	1.384 (7)	N1—H1	0.861 (2)
O1—C1—N1	125.1 (4)	C8—C9—C10	115.7 (6)
O1—C1—C2	118.7 (4)	C8—C9—C14	123.7 (5)
N1—C1—C2	116.2 (4)	C10—C9—C14	120.6 (5)
C3—C2—C7	118.0 (5)	C11—C10—C9	121.7 (6)
C3—C2—C1	123.3 (5)	C11—C10—H10A	119.2
C7—C2—C1	118.7 (5)	C9—C10—H10A	119.2
C2—C3—C4	121.0 (5)	C10—C11—C12	121.1 (7)
C2—C3—Cl1	121.1 (4)	C10—C11—H11A	119.5
C4—C3—Cl1	117.9 (5)	C12—C11—H11A	119.5
C3—C4—C5	120.2 (6)	C13—C12—C11	119.6 (6)
C3—C4—H4A	119.9	C13—C12—H12A	120.2
C5—C4—H4A	119.9	C11—C12—H12A	120.2
C6—C5—C4	119.2 (7)	C12—C13—C8	120.1 (6)
C6—C5—H5A	120.4	C12—C13—H13A	120.0
C4—C5—H5A	120.4	C8—C13—H13A	120.0
C7—C6—C5	119.9 (6)	C9—C14—H14C	109.5
C7—C6—H6A	120.1	C9—C14—H14B	109.5
C5—C6—H6A	120.1	H14C—C14—H14B	109.5
C6—C7—C2	121.6 (6)	C9—C14—H14A	109.5
C6—C7—H7A	119.2	H14C—C14—H14A	109.5
C2—C7—H7A	119.2	H14B—C14—H14A	109.5
C9—C8—C13	121.6 (5)	C1—N1—C8	122.0 (4)
C9—C8—N1	118.8 (5)	C1—N1—H1	118 (4)
C13—C8—N1	119.6 (5)	C8—N1—H1	120 (4)
O1—C1—C2—C3	−59.1 (7)	C13—C8—C9—C10	−2.0 (7)
N1—C1—C2—C3	122.1 (5)	N1—C8—C9—C10	−179.2 (4)
O1—C1—C2—C7	120.7 (5)	C13—C8—C9—C14	177.8 (5)
N1—C1—C2—C7	−58.2 (6)	N1—C8—C9—C14	0.6 (7)
C7—C2—C3—C4	−3.2 (8)	C8—C9—C10—C11	−2.9 (9)
C1—C2—C3—C4	176.6 (4)	C14—C9—C10—C11	177.2 (6)
C7—C2—C3—Cl1	179.0 (4)	C9—C10—C11—C12	5.8 (10)
C1—C2—C3—Cl1	−1.2 (7)	C10—C11—C12—C13	−3.6 (10)
C2—C3—C4—C5	1.6 (8)	C11—C12—C13—C8	−1.3 (8)
Cl1—C3—C4—C5	179.5 (5)	C9—C8—C13—C12	4.2 (8)
C3—C4—C5—C6	0.2 (9)	N1—C8—C13—C12	−178.7 (4)
C4—C5—C6—C7	−0.3 (9)	O1—C1—N1—C8	3.0 (7)
C5—C6—C7—C2	−1.4 (9)	C2—C1—N1—C8	−178.3 (5)
C3—C2—C7—C6	3.1 (8)	C9—C8—N1—C1	−126.3 (5)
C1—C2—C7—C6	−176.7 (5)	C13—C8—N1—C1	56.4 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86 (1)	2.00 (1)	2.853 (5)	171 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86 (1)	2.00 (1)	2.853 (5)	171 (5)

Symmetry code: (i) .