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

In the structure of the title compound (N2CP2MBA), C(14)H(12)ClNO, the conformations of the N-H and C=O bonds are trans to each other. Furthermore, the conformation of the N-H bond is syn to the ortho-chloro group in the aniline ring and the C=O bond is syn to the ortho-methyl substituent in the benzoyl ring, similar to what is observed in 2-chloro-N-(2-chloro-phen-yl)benzamide and 2-methyl-N-phenyl-benzamide. The amide group makes almost the same dihedral angles of 41.2 (14) and 42.2 (13)° with the aniline and benzoyl rings, respectively, while the dihedral angle between the benzoyl and aniline rings is only 7.4 (3)°. The mol-ecules in N2CP2MBA are packed into chains through N-H⋯O hydrogen bonds.

Related literature

For related literature, see: Gowda et al. (2003 ▶, 2008 ▶); Gowda, Foro et al. (2007 ▶); Gowda, Sowmya et al. (2007 ▶).

Experimental

Crystal data

C14H12ClNO

M = 245.70

Monoclinic,

a = 4.8881 (4) Å

b = 24.318 (2) Å

c = 10.0562 (8) Å

β = 90.373 (6)°

V = 1195.34 (17) Å3

Z = 4

Cu Kα radiation

μ = 2.67 mm−1

T = 299 (2) K

0.55 × 0.13 × 0.05 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.695, T max = 0.878

2264 measured reflections

2126 independent reflections

1695 reflections with I > 2σ(I)

R int = 0.050

3 standard reflections frequency: 120 min intensity decay: 1.5%

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.333

S = 1.49

2126 reflections

158 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.58 e Å−3

Δρmin = −0.64 e Å−3

Data collection: CAD-4-PC Software (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC Software; data reduction: REDU4 (Stoe & Cie, 1987 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808020229/bg2196sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020229/bg2196Isup2.hkl

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

C14H12ClNO	F000 = 512
Mr = 245.70	Dx = 1.365 Mg m−3
Monoclinic, P21/n	Cu Kα radiation λ = 1.54180 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 4.8881 (4) Å	θ = 7.3–21.6º
b = 24.318 (2) Å	µ = 2.67 mm−1
c = 10.0562 (8) Å	T = 299 (2) K
β = 90.373 (6)º	Rod, colourless
V = 1195.34 (17) Å3	0.55 × 0.13 × 0.05 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.050
Radiation source: fine-focus sealed tube	θmax = 66.9º
Monochromator: graphite	θmin = 3.6º
T = 299(2) K	h = −5→5
ω/2θ scans	k = −29→0
Absorption correction: ψ scan(North et al., 1968)	l = −12→1
Tmin = 0.695, Tmax = 0.878	3 standard reflections
2264 measured reflections	every 120 min
2126 independent reflections	intensity decay: 1.5%
1695 reflections with I > 2σ(I)

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)] = 0.067	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.333	w = 1/[σ2(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3
S = 1.49	(Δ/σ)max < 0.001
2126 reflections	Δρmax = 0.59 e Å−3
158 parameters	Δρmin = −0.64 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.5268 (8)	0.58356 (18)	0.9109 (4)	0.0391 (10)
C2	0.3925 (9)	0.59484 (18)	0.7921 (5)	0.0435 (10)
C3	0.4354 (12)	0.5627 (2)	0.6800 (5)	0.0561 (13)
H3	0.3425	0.5707	0.6014	0.067*
C4	0.6138 (13)	0.5193 (2)	0.6847 (5)	0.0623 (15)
H4	0.6438	0.4981	0.6092	0.075*
C5	0.7482 (11)	0.5073 (2)	0.8016 (5)	0.0576 (13)
H5	0.8674	0.4776	0.8058	0.069*
C6	0.7067 (10)	0.5393 (2)	0.9124 (5)	0.0514 (12)
H6	0.8014	0.5311	0.9904	0.062*
C7	0.6651 (8)	0.63040 (19)	1.1158 (4)	0.0392 (10)
C8	0.5627 (8)	0.66363 (17)	1.2305 (4)	0.0377 (10)
C9	0.6654 (10)	0.65413 (18)	1.3586 (5)	0.0443 (11)
C10	0.5648 (11)	0.6868 (2)	1.4611 (5)	0.0554 (13)
H10	0.6293	0.6812	1.5473	0.067*
C11	0.3720 (12)	0.7272 (2)	1.4380 (6)	0.0632 (15)
H11	0.3062	0.7481	1.5083	0.076*
C12	0.2767 (11)	0.7365 (2)	1.3106 (6)	0.0608 (14)
H12	0.1495	0.7642	1.2945	0.073*
C13	0.3710 (10)	0.7046 (2)	1.2075 (5)	0.0493 (11)
H13	0.3054	0.7106	1.1216	0.059*
C14	0.8698 (11)	0.6100 (2)	1.3901 (5)	0.0549 (13)
H14A	1.0390	0.6179	1.3461	0.066*
H14B	0.8010	0.5751	1.3599	0.066*
H14C	0.9004	0.6086	1.4844	0.066*
N1	0.4730 (7)	0.61465 (17)	1.0252 (4)	0.0439 (9)
H1N	0.306 (13)	0.623 (2)	1.050 (5)	0.053*
O1	0.9068 (6)	0.61743 (16)	1.1044 (3)	0.0565 (10)
Cl1	0.1723 (3)	0.65063 (6)	0.78357 (13)	0.0601 (6)

	U11	U22	U33	U12	U13	U23
C1	0.027 (2)	0.052 (2)	0.038 (2)	0.0007 (16)	0.0020 (16)	−0.0012 (17)
C2	0.037 (2)	0.050 (2)	0.043 (2)	0.0006 (18)	−0.0003 (18)	0.0006 (19)
C3	0.057 (3)	0.067 (3)	0.044 (2)	0.005 (2)	−0.011 (2)	−0.004 (2)
C4	0.067 (3)	0.070 (3)	0.050 (3)	0.011 (3)	0.001 (2)	−0.019 (2)
C5	0.058 (3)	0.058 (3)	0.057 (3)	0.016 (2)	0.003 (2)	−0.005 (2)
C6	0.045 (3)	0.065 (3)	0.044 (2)	0.005 (2)	−0.0031 (19)	0.001 (2)
C7	0.025 (2)	0.058 (3)	0.035 (2)	−0.0011 (17)	0.0025 (16)	0.0022 (18)
C8	0.0257 (19)	0.046 (2)	0.041 (2)	−0.0081 (16)	0.0057 (16)	−0.0031 (18)
C9	0.040 (2)	0.053 (3)	0.041 (2)	−0.0059 (18)	0.0039 (19)	−0.0012 (18)
C10	0.058 (3)	0.065 (3)	0.044 (2)	−0.014 (2)	0.004 (2)	−0.014 (2)
C11	0.058 (3)	0.064 (3)	0.067 (3)	−0.001 (2)	0.014 (3)	−0.028 (3)
C12	0.048 (3)	0.048 (3)	0.086 (4)	0.001 (2)	0.005 (3)	−0.015 (2)
C13	0.039 (2)	0.057 (3)	0.052 (3)	0.0017 (19)	0.002 (2)	0.001 (2)
C14	0.044 (3)	0.072 (3)	0.048 (3)	0.006 (2)	−0.003 (2)	0.007 (2)
N1	0.0276 (18)	0.066 (2)	0.0378 (19)	0.0020 (16)	−0.0001 (15)	−0.0057 (17)
O1	0.0251 (16)	0.092 (3)	0.0523 (19)	0.0015 (16)	0.0009 (13)	−0.0153 (18)
Cl1	0.0564 (9)	0.0687 (10)	0.0551 (9)	0.0175 (5)	−0.0062 (6)	0.0061 (5)

C1—C2	1.387 (6)	C8—C13	1.386 (7)
C1—C6	1.390 (7)	C8—C9	1.399 (6)
C1—N1	1.402 (5)	C9—C10	1.394 (6)
C2—C3	1.388 (7)	C9—C14	1.499 (7)
C2—Cl1	1.734 (5)	C10—C11	1.380 (8)
C3—C4	1.369 (7)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.379 (8)
C4—C5	1.375 (8)	C11—H11	0.9300
C4—H4	0.9300	C12—C13	1.377 (7)
C5—C6	1.374 (7)	C12—H12	0.9300
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	C14—H14A	0.9600
C7—O1	1.229 (5)	C14—H14B	0.9600
C7—N1	1.359 (5)	C14—H14C	0.9600
C7—C8	1.497 (6)	N1—H1N	0.88 (6)
C2—C1—C6	117.3 (4)	C10—C9—C8	117.4 (5)
C2—C1—N1	120.6 (4)	C10—C9—C14	119.3 (4)
C6—C1—N1	122.1 (4)	C8—C9—C14	123.2 (4)
C1—C2—C3	121.0 (4)	C11—C10—C9	121.7 (5)
C1—C2—Cl1	119.2 (3)	C11—C10—H10	119.2
C3—C2—Cl1	119.8 (4)	C9—C10—H10	119.2
C4—C3—C2	120.4 (5)	C12—C11—C10	120.0 (5)
C4—C3—H3	119.8	C12—C11—H11	120.0
C2—C3—H3	119.8	C10—C11—H11	120.0
C3—C4—C5	119.6 (5)	C13—C12—C11	119.6 (5)
C3—C4—H4	120.2	C13—C12—H12	120.2
C5—C4—H4	120.2	C11—C12—H12	120.2
C6—C5—C4	120.1 (5)	C12—C13—C8	120.6 (5)
C6—C5—H5	120.0	C12—C13—H13	119.7
C4—C5—H5	120.0	C8—C13—H13	119.7
C5—C6—C1	121.7 (4)	C9—C14—H14A	109.5
C5—C6—H6	119.1	C9—C14—H14B	109.5
C1—C6—H6	119.1	H14A—C14—H14B	109.5
O1—C7—N1	121.7 (4)	C9—C14—H14C	109.5
O1—C7—C8	122.5 (4)	H14A—C14—H14C	109.5
N1—C7—C8	115.8 (3)	H14B—C14—H14C	109.5
C13—C8—C9	120.7 (4)	C7—N1—C1	124.7 (4)
C13—C8—C7	119.2 (4)	C7—N1—H1N	113 (3)
C9—C8—C7	120.0 (4)	C1—N1—H1N	122 (3)
C6—C1—C2—C3	0.5 (7)	C13—C8—C9—C10	0.8 (6)
N1—C1—C2—C3	−177.1 (4)	C7—C8—C9—C10	179.2 (4)
C6—C1—C2—Cl1	−178.4 (3)	C13—C8—C9—C14	179.1 (4)
N1—C1—C2—Cl1	3.9 (6)	C7—C8—C9—C14	−2.5 (6)
C1—C2—C3—C4	−0.5 (8)	C8—C9—C10—C11	−0.2 (7)
Cl1—C2—C3—C4	178.5 (4)	C14—C9—C10—C11	−178.6 (5)
C2—C3—C4—C5	0.7 (9)	C9—C10—C11—C12	−0.9 (8)
C3—C4—C5—C6	−1.0 (9)	C10—C11—C12—C13	1.3 (9)
C4—C5—C6—C1	1.1 (8)	C11—C12—C13—C8	−0.7 (8)
C2—C1—C6—C5	−0.8 (7)	C9—C8—C13—C12	−0.4 (7)
N1—C1—C6—C5	176.8 (5)	C7—C8—C13—C12	−178.8 (4)
O1—C7—C8—C13	139.0 (5)	O1—C7—N1—C1	−1.0 (7)
N1—C7—C8—C13	−41.8 (6)	C8—C7—N1—C1	179.8 (4)
O1—C7—C8—C9	−39.4 (6)	C2—C1—N1—C7	−141.4 (5)
N1—C7—C8—C9	139.8 (4)	C6—C1—N1—C7	41.1 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.88 (6)	2.03 (6)	2.886 (5)	163 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.88 (6)	2.03 (6)	2.886 (5)	163 (5)

Symmetry code: (i) .