2-Chloro-N-(3,4-dimethyl-phen-yl)benzamide.

In the title compound, C(15)H(14)ClNO, the conformation of the N-H bond is anti to the meta-methyl group in the aniline ring, while that of the C=O bond is anti to the ortho-chloro group in the benzoyl ring. The mean planes through the two benzene rings make a dihedral angle of 80.8 (2)°. In the crystal, mol-ecules are linked by inter-molecular N-H⋯O hydrogen bonds, forming column-like chains along the b axis.

Related literature

For the preparation of the title compound, see: Gowda et al. (2003 ▶). For our studies on the effects of substituents on the structures of N-(ar­yl)-amides, see: Bhat & Gowda (2000 ▶); Gowda et al. (2007 ▶) and on N-(ar­yl)-benzamides, see: Gowda et al. (2009 ▶); Gowda et al. (2010 ▶). For related structure, see: Bowes et al. (2003 ▶).

Experimental

Crystal data

C15H14ClNO

M = 259.72

Monoclinic,

a = 20.893 (2) Å

b = 7.259 (1) Å

c = 8.970 (1) Å

β = 91.95 (1)°

V = 1359.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 293 K

0.30 × 0.26 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.924, T max = 0.958

4865 measured reflections

2489 independent reflections

1570 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.076

wR(F 2) = 0.217

S = 1.10

2489 reflections

168 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.28 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/S1600536811027267/nc2237sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811027267/nc2237Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811027267/nc2237Isup3.cml

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

C15H14ClNO	F(000) = 544
Mr = 259.72	Dx = 1.269 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 872 reflections
a = 20.893 (2) Å	θ = 2.8–27.9°
b = 7.259 (1) Å	µ = 0.27 mm−1
c = 8.970 (1) Å	T = 293 K
β = 91.95 (1)°	Prism, light brown
V = 1359.6 (3) Å3	0.30 × 0.26 × 0.16 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2489 independent reflections
Radiation source: fine-focus sealed tube	1570 reflections with I > 2σ(I)
graphite	Rint = 0.027
Rotation method data acquisition using ω scans	θmax = 25.4°, θmin = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −25→16
Tmin = 0.924, Tmax = 0.958	k = −8→8
4865 measured reflections	l = −10→10

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)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.217	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.074P)2 + 2.1954P] where P = (Fo2 + 2Fc2)/3
2489 reflections	(Δ/σ)max < 0.001
168 parameters	Δρmax = 0.32 e Å−3
1 restraint	Δρmin = −0.28 e Å−3

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.2020 (2)	0.0975 (6)	0.1139 (4)	0.0465 (11)
C2	0.15704 (19)	0.1524 (7)	0.0060 (4)	0.0509 (11)
H2	0.1555	0.2746	−0.0251	0.061*
C3	0.11372 (19)	0.0239 (8)	−0.0568 (4)	0.0549 (13)
C4	0.1162 (2)	−0.1594 (7)	−0.0111 (5)	0.0571 (13)
C5	0.1615 (2)	−0.2089 (8)	0.0966 (5)	0.0629 (13)
H5	0.1635	−0.3308	0.1283	0.075*
C6	0.2037 (2)	−0.0836 (7)	0.1584 (5)	0.0572 (12)
H6	0.2338	−0.1215	0.2309	0.069*
C7	0.2788 (2)	0.3563 (6)	0.1115 (4)	0.0443 (10)
C8	0.3274 (2)	0.4554 (6)	0.2085 (4)	0.0446 (10)
C9	0.3914 (2)	0.4586 (6)	0.1757 (5)	0.0545 (12)
C10	0.4350 (2)	0.5547 (8)	0.2628 (6)	0.0706 (14)
H10	0.4782	0.5528	0.2414	0.085*
C11	0.4141 (3)	0.6539 (8)	0.3824 (6)	0.0832 (18)
H11	0.4433	0.7225	0.4398	0.100*
C12	0.3509 (3)	0.6532 (8)	0.4181 (6)	0.0733 (15)
H12	0.3372	0.7191	0.5000	0.088*
C13	0.3083 (2)	0.5538 (7)	0.3309 (5)	0.0566 (12)
H13	0.2653	0.5526	0.3548	0.068*
C14	0.0649 (2)	0.0927 (9)	−0.1727 (6)	0.0855 (19)
H14A	0.0722	0.2210	−0.1915	0.103*
H14B	0.0225	0.0762	−0.1365	0.103*
H14C	0.0690	0.0243	−0.2634	0.103*
C15	0.0705 (3)	−0.3013 (9)	−0.0752 (6)	0.0836 (18)
H15A	0.0740	−0.3054	−0.1816	0.100*
H15B	0.0275	−0.2691	−0.0511	0.100*
H15C	0.0810	−0.4199	−0.0337	0.100*
N1	0.24717 (17)	0.2223 (5)	0.1808 (3)	0.0506 (10)
H1N	0.260 (2)	0.189 (6)	0.270 (3)	0.061*
O1	0.26938 (16)	0.3992 (5)	−0.0198 (3)	0.0633 (9)
Cl1	0.41840 (7)	0.3313 (2)	0.02704 (17)	0.0920 (6)

	U11	U22	U33	U12	U13	U23
C1	0.047 (2)	0.061 (3)	0.031 (2)	−0.005 (2)	−0.0019 (17)	−0.0008 (19)
C2	0.047 (2)	0.064 (3)	0.042 (2)	0.003 (2)	−0.0029 (18)	−0.002 (2)
C3	0.038 (2)	0.089 (4)	0.037 (2)	0.001 (2)	−0.0061 (17)	−0.010 (2)
C4	0.052 (3)	0.076 (4)	0.044 (2)	−0.014 (3)	0.0045 (19)	−0.009 (2)
C5	0.069 (3)	0.064 (3)	0.055 (3)	−0.015 (3)	−0.002 (2)	0.002 (2)
C6	0.058 (3)	0.065 (3)	0.048 (2)	−0.011 (2)	−0.010 (2)	0.005 (2)
C7	0.051 (2)	0.049 (3)	0.032 (2)	−0.001 (2)	−0.0033 (17)	−0.0021 (19)
C8	0.055 (3)	0.040 (2)	0.037 (2)	−0.003 (2)	−0.0077 (18)	0.0038 (18)
C9	0.058 (3)	0.052 (3)	0.053 (3)	−0.003 (2)	−0.003 (2)	−0.003 (2)
C10	0.056 (3)	0.077 (4)	0.079 (4)	−0.013 (3)	−0.002 (3)	−0.001 (3)
C11	0.082 (4)	0.083 (4)	0.083 (4)	−0.029 (3)	−0.012 (3)	−0.022 (3)
C12	0.084 (4)	0.074 (4)	0.062 (3)	−0.013 (3)	0.000 (3)	−0.025 (3)
C13	0.068 (3)	0.055 (3)	0.047 (2)	−0.006 (2)	0.000 (2)	−0.010 (2)
C14	0.064 (3)	0.127 (5)	0.064 (3)	0.011 (3)	−0.024 (3)	−0.009 (3)
C15	0.079 (4)	0.107 (5)	0.064 (3)	−0.034 (4)	0.000 (3)	−0.019 (3)
N1	0.059 (2)	0.060 (2)	0.0313 (17)	−0.015 (2)	−0.0121 (16)	0.0037 (17)
O1	0.082 (2)	0.073 (2)	0.0339 (16)	−0.0139 (18)	−0.0117 (14)	0.0075 (15)
Cl1	0.0697 (9)	0.1153 (14)	0.0917 (11)	0.0070 (9)	0.0146 (7)	−0.0370 (9)

C1—C6	1.375 (6)	C9—C10	1.371 (6)
C1—C2	1.384 (6)	C9—Cl1	1.732 (5)
C1—N1	1.426 (5)	C10—C11	1.375 (7)
C2—C3	1.404 (6)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.369 (7)
C3—C4	1.393 (7)	C11—H11	0.9300
C3—C14	1.516 (6)	C12—C13	1.370 (7)
C4—C5	1.377 (7)	C12—H12	0.9300
C4—C15	1.504 (7)	C13—H13	0.9300
C5—C6	1.371 (6)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—H6	0.9300	C14—H14C	0.9600
C7—O1	1.228 (4)	C15—H15A	0.9600
C7—N1	1.340 (5)	C15—H15B	0.9600
C7—C8	1.500 (5)	C15—H15C	0.9600
C8—C9	1.379 (6)	N1—H1N	0.866 (19)
C8—C13	1.380 (6)
C6—C1—C2	119.3 (4)	C9—C10—C11	119.3 (5)
C6—C1—N1	118.3 (4)	C9—C10—H10	120.4
C2—C1—N1	122.4 (4)	C11—C10—H10	120.4
C1—C2—C3	120.1 (5)	C12—C11—C10	121.0 (5)
C1—C2—H2	119.9	C12—C11—H11	119.5
C3—C2—H2	119.9	C10—C11—H11	119.5
C4—C3—C2	120.0 (4)	C11—C12—C13	118.8 (5)
C4—C3—C14	122.2 (5)	C11—C12—H12	120.6
C2—C3—C14	117.8 (5)	C13—C12—H12	120.6
C5—C4—C3	118.2 (4)	C12—C13—C8	121.8 (5)
C5—C4—C15	120.1 (5)	C12—C13—H13	119.1
C3—C4—C15	121.7 (4)	C8—C13—H13	119.1
C6—C5—C4	121.9 (5)	C3—C14—H14A	109.5
C6—C5—H5	119.0	C3—C14—H14B	109.5
C4—C5—H5	119.0	H14A—C14—H14B	109.5
C5—C6—C1	120.4 (4)	C3—C14—H14C	109.5
C5—C6—H6	119.8	H14A—C14—H14C	109.5
C1—C6—H6	119.8	H14B—C14—H14C	109.5
O1—C7—N1	124.3 (4)	C4—C15—H15A	109.5
O1—C7—C8	121.2 (4)	C4—C15—H15B	109.5
N1—C7—C8	114.5 (3)	H15A—C15—H15B	109.5
C9—C8—C13	118.1 (4)	C4—C15—H15C	109.5
C9—C8—C7	121.8 (4)	H15A—C15—H15C	109.5
C13—C8—C7	120.1 (4)	H15B—C15—H15C	109.5
C10—C9—C8	121.1 (4)	C7—N1—C1	126.6 (3)
C10—C9—Cl1	118.9 (4)	C7—N1—H1N	119 (3)
C8—C9—Cl1	119.9 (3)	C1—N1—H1N	113 (3)
C6—C1—C2—C3	0.1 (6)	N1—C7—C8—C13	−62.7 (5)
N1—C1—C2—C3	179.8 (4)	C13—C8—C9—C10	0.8 (7)
C1—C2—C3—C4	−0.4 (6)	C7—C8—C9—C10	177.9 (4)
C1—C2—C3—C14	179.0 (4)	C13—C8—C9—Cl1	177.8 (3)
C2—C3—C4—C5	0.5 (6)	C7—C8—C9—Cl1	−5.0 (6)
C14—C3—C4—C5	−178.9 (4)	C8—C9—C10—C11	−2.0 (8)
C2—C3—C4—C15	179.8 (4)	Cl1—C9—C10—C11	−179.1 (4)
C14—C3—C4—C15	0.4 (7)	C9—C10—C11—C12	2.1 (9)
C3—C4—C5—C6	−0.3 (7)	C10—C11—C12—C13	−1.0 (9)
C15—C4—C5—C6	−179.6 (5)	C11—C12—C13—C8	−0.2 (8)
C4—C5—C6—C1	0.0 (7)	C9—C8—C13—C12	0.3 (7)
C2—C1—C6—C5	0.1 (7)	C7—C8—C13—C12	−176.9 (5)
N1—C1—C6—C5	−179.6 (4)	O1—C7—N1—C1	5.7 (7)
O1—C7—C8—C9	−60.5 (6)	C8—C7—N1—C1	−175.1 (4)
N1—C7—C8—C9	120.2 (5)	C6—C1—N1—C7	139.5 (5)
O1—C7—C8—C13	116.5 (5)	C2—C1—N1—C7	−40.1 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.87 (2)	2.00 (2)	2.850 (4)	168 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.87 (2)	2.00 (2)	2.850 (4)	168 (4)

Symmetry code: (i) .