2-Chloro-N-(3-methyl-phen-yl)benzamide.

In the structure of the title compound, C(14)H(12)ClNO, the ortho-Cl atom in the benzoyl ring is positioned syn to the C=O bond, while the meta-methyl group in the aniline ring is positioned anti to the N-H bond. The amide group forms dihedral angles of 60.1 (1) and 22.0 (1)°, respectively, with the benzoyl and aniline rings, while the angle between these rings is 38.7 (1)°. The crystal structure is stabilized by N-H⋯O hydrogen bonds, which give rise to infinite chains running along the c axis.

Related literature

For studies, including ours, on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Bowes et al. (2003 ▶); Gowda et al. (1999 ▶, 2006 ▶); Rodrigues et al. (2011 ▶); Saeed et al. (2010 ▶); for N-(ar­yl)-methane­n class="Chemical">sulfonamides, see: Gowda et al. (2007 ▶); for N-chloro­aryl­amides, see: Jyothi & Gowda (2004 ▶); and for N-bromo­aryl­sulfonamides, see: Usha & Gowda (2006 ▶).

Experimental

Crystal data

C14H12ClNO

M = 245.70

Tetragonal,

a = 8.8751 (3) Å

c = 15.9642 (5) Å

V = 1257.45 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 295 K

0.4 × 0.3 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur System diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.898, T max = 0.942

8244 measured reflections

2552 independent reflections

1757 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.069

S = 1.04

2552 reflections

158 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.08 e Å−3

Δρmin = −0.11 e Å−3

Absolute structure: Flack (1983 ▶), 1229 Friedel pairs

Flack parameter: 0.00 (6)

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis n class="Disease">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/S1600536812005739/sj5196sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005739/sj5196Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812005739/sj5196Isup3.cml

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

C14H12ClNO	Dx = 1.298 Mg m−3
Mr = 245.70	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P43	Cell parameters from 2552 reflections
a = 8.8751 (3) Å	θ = 3.4–29.3°
c = 15.9642 (5) Å	µ = 0.29 mm−1
V = 1257.45 (6) Å3	T = 295 K
Z = 4	Plate, colourless
F(000) = 512	0.4 × 0.3 × 0.2 mm

Oxford Diffraction Xcalibur System diffractometer	2552 independent reflections
Radiation source: fine-focus sealed tube	1757 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
Detector resolution: 0 pixels mm-1	θmax = 26.4°, θmin = 4.1°
ω scans with κ offsets	h = −10→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −11→10
Tmin = 0.898, Tmax = 0.942	l = −19→19
8244 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)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.069	w = 1/[σ2(Fo2) + (0.0348P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2552 reflections	Δρmax = 0.08 e Å−3
158 parameters	Δρmin = −0.11 e Å−3
2 restraints	Absolute structure: Flack (1983), ???? Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (6)

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	0.6060 (2)	0.6255 (2)	0.21616 (9)	0.0579 (4)
C2	0.6965 (2)	0.7340 (2)	0.25296 (11)	0.0731 (5)
C3	0.6388 (4)	0.8363 (2)	0.30991 (13)	0.1015 (8)
H3	0.7002	0.9103	0.3330	0.122*
C4	0.4900 (5)	0.8268 (3)	0.33167 (17)	0.1176 (10)
H4	0.4505	0.8952	0.3700	0.141*
C5	0.3986 (3)	0.7188 (4)	0.29813 (18)	0.1124 (9)
H5	0.2979	0.7131	0.3140	0.135*
C6	0.4562 (3)	0.6180 (2)	0.24059 (14)	0.0819 (6)
H6	0.3939	0.5442	0.2180	0.098*
C7	0.66413 (19)	0.52431 (19)	0.14825 (9)	0.0525 (4)
C8	0.69202 (18)	0.25396 (19)	0.11204 (9)	0.0529 (4)
C9	0.7955 (2)	0.2664 (2)	0.04811 (10)	0.0582 (4)
H9	0.8393	0.3594	0.0368	0.070*
C10	0.8357 (2)	0.1411 (2)	−0.00002 (10)	0.0678 (5)
C11	0.7689 (3)	0.0059 (3)	0.01807 (13)	0.0839 (6)
H11	0.7941	−0.0786	−0.0134	0.101*
C12	0.6663 (3)	−0.0075 (2)	0.08115 (15)	0.0927 (7)
H12	0.6228	−0.1007	0.0923	0.111*
C13	0.6264 (2)	0.1167 (2)	0.12884 (12)	0.0732 (5)
H13	0.5560	0.1075	0.1717	0.088*
C14	0.9504 (3)	0.1563 (3)	−0.06817 (13)	0.0986 (7)
H14A	0.9645	0.0605	−0.0950	0.148*
H14B	1.0442	0.1896	−0.0447	0.148*
H14C	0.9160	0.2285	−0.1086	0.148*
N1	0.65297 (16)	0.37678 (15)	0.16483 (7)	0.0541 (3)
H1	0.6216 (16)	0.3554 (18)	0.2143 (4)	0.057 (5)*
O1	0.71348 (15)	0.57708 (12)	0.08283 (6)	0.0695 (3)
Cl1	0.88575 (8)	0.74156 (9)	0.22927 (4)	0.1238 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0768 (13)	0.0532 (10)	0.0435 (9)	0.0070 (9)	0.0009 (8)	0.0051 (8)
C2	0.1011 (15)	0.0678 (12)	0.0505 (10)	−0.0026 (11)	0.0069 (10)	−0.0031 (9)
C3	0.167 (3)	0.0738 (15)	0.0636 (13)	−0.0023 (15)	0.0112 (15)	−0.0163 (12)
C4	0.184 (3)	0.0806 (18)	0.0882 (17)	0.052 (2)	0.024 (2)	−0.0110 (15)
C5	0.106 (2)	0.122 (2)	0.1091 (19)	0.0456 (19)	0.0298 (16)	−0.0028 (18)
C6	0.0827 (15)	0.0798 (14)	0.0831 (13)	0.0154 (11)	0.0071 (12)	−0.0038 (12)
C7	0.0604 (10)	0.0576 (11)	0.0397 (8)	0.0039 (8)	−0.0057 (7)	0.0000 (8)
C8	0.0618 (11)	0.0561 (11)	0.0407 (8)	0.0074 (9)	−0.0086 (8)	0.0017 (7)
C9	0.0647 (11)	0.0597 (11)	0.0503 (9)	0.0074 (8)	−0.0004 (8)	−0.0018 (8)
C10	0.0762 (13)	0.0770 (14)	0.0504 (10)	0.0228 (11)	−0.0066 (9)	−0.0098 (9)
C11	0.1158 (18)	0.0646 (14)	0.0714 (13)	0.0147 (12)	−0.0142 (13)	−0.0211 (10)
C12	0.134 (2)	0.0550 (13)	0.0897 (15)	−0.0091 (12)	−0.0063 (15)	−0.0062 (12)
C13	0.0945 (15)	0.0604 (13)	0.0647 (11)	−0.0058 (10)	0.0061 (10)	0.0001 (10)
C14	0.1021 (18)	0.118 (2)	0.0757 (13)	0.0372 (14)	0.0136 (12)	−0.0137 (13)
N1	0.0747 (10)	0.0516 (9)	0.0361 (7)	0.0009 (7)	0.0059 (6)	0.0023 (6)
O1	0.1070 (10)	0.0619 (8)	0.0397 (6)	−0.0015 (6)	0.0060 (6)	0.0053 (6)
Cl1	0.1097 (5)	0.1673 (7)	0.0943 (4)	−0.0532 (4)	0.0089 (3)	−0.0407 (4)

C1—C2	1.384 (3)	C8—C9	1.378 (2)
C1—C6	1.387 (3)	C8—N1	1.421 (2)
C1—C7	1.499 (2)	C9—C10	1.398 (2)
C2—C3	1.383 (3)	C9—H9	0.9300
C2—Cl1	1.723 (2)	C10—C11	1.369 (3)
C3—C4	1.368 (4)	C10—C14	1.496 (3)
C3—H3	0.9300	C11—C12	1.363 (3)
C4—C5	1.366 (4)	C11—H11	0.9300
C4—H4	0.9300	C12—C13	1.386 (3)
C5—C6	1.381 (3)	C12—H12	0.9300
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	C14—H14A	0.9600
C7—O1	1.2254 (19)	C14—H14B	0.9600
C7—N1	1.340 (2)	C14—H14C	0.9600
C8—C13	1.376 (2)	N1—H1	0.859 (2)
C2—C1—C6	118.06 (17)	C8—C9—C10	120.92 (17)
C2—C1—C7	121.60 (16)	C8—C9—H9	119.5
C6—C1—C7	120.25 (17)	C10—C9—H9	119.5
C3—C2—C1	121.4 (2)	C11—C10—C9	118.07 (18)
C3—C2—Cl1	118.66 (19)	C11—C10—C14	121.81 (18)
C1—C2—Cl1	119.96 (14)	C9—C10—C14	120.12 (19)
C4—C3—C2	119.0 (2)	C12—C11—C10	121.44 (18)
C4—C3—H3	120.5	C12—C11—H11	119.3
C2—C3—H3	120.5	C10—C11—H11	119.3
C5—C4—C3	121.1 (2)	C11—C12—C13	120.5 (2)
C5—C4—H4	119.4	C11—C12—H12	119.7
C3—C4—H4	119.4	C13—C12—H12	119.7
C4—C5—C6	119.7 (3)	C8—C13—C12	119.23 (18)
C4—C5—H5	120.2	C8—C13—H13	120.4
C6—C5—H5	120.2	C12—C13—H13	120.4
C5—C6—C1	120.7 (2)	C10—C14—H14A	109.5
C5—C6—H6	119.6	C10—C14—H14B	109.5
C1—C6—H6	119.6	H14A—C14—H14B	109.5
O1—C7—N1	124.64 (14)	C10—C14—H14C	109.5
O1—C7—C1	120.67 (15)	H14A—C14—H14C	109.5
N1—C7—C1	114.67 (14)	H14B—C14—H14C	109.5
C13—C8—C9	119.83 (16)	C7—N1—C8	127.93 (13)
C13—C8—N1	117.39 (15)	C7—N1—H1	115.0 (11)
C9—C8—N1	122.74 (16)	C8—N1—H1	117.1 (11)
C6—C1—C2—C3	−2.6 (3)	C13—C8—C9—C10	−0.3 (2)
C7—C1—C2—C3	173.88 (17)	N1—C8—C9—C10	177.13 (14)
C6—C1—C2—Cl1	176.38 (15)	C8—C9—C10—C11	0.2 (2)
C7—C1—C2—Cl1	−7.1 (2)	C8—C9—C10—C14	−178.91 (17)
C1—C2—C3—C4	1.8 (3)	C9—C10—C11—C12	−0.2 (3)
Cl1—C2—C3—C4	−177.27 (19)	C14—C10—C11—C12	178.9 (2)
C2—C3—C4—C5	−0.1 (4)	C10—C11—C12—C13	0.2 (3)
C3—C4—C5—C6	−0.7 (4)	C9—C8—C13—C12	0.3 (3)
C4—C5—C6—C1	−0.3 (4)	N1—C8—C13—C12	−177.23 (16)
C2—C1—C6—C5	1.9 (3)	C11—C12—C13—C8	−0.3 (3)
C7—C1—C6—C5	−174.69 (19)	O1—C7—N1—C8	−1.0 (3)
C2—C1—C7—O1	−58.9 (2)	C1—C7—N1—C8	177.16 (15)
C6—C1—C7—O1	117.55 (19)	C13—C8—N1—C7	−158.57 (16)
C2—C1—C7—N1	122.85 (17)	C9—C8—N1—C7	24.0 (2)
C6—C1—C7—N1	−60.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86 (1)	2.03 (1)	2.8790 (16)	171 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86 (1)	2.03 (1)	2.8790 (16)	171 (2)

Symmetry code: (i) .