N-(4-Chloro-phen-yl)-2-methyl-benzamide.

In the structure of the title compound, C(14)H(12)ClNO, the N-H and C=O bonds are trans to each other. Furthermore, the C=O bond is syn to the ortho-methyl group in the benzoyl ring, similar to what is observed in 2-methyl-N-(4-methyl-phen-yl)benzamide and 2-methyl-N-phenyl-benzamide. The amide linkage (-NHCO-) makes dihedral angles of 36.9 (7) and 46.4 (5)° with the aniline and benzoyl rings, respectively, while the dihedral angle between the benzoyl and aniline rings is 83.1 (1)°. In the crystal structure, mol-ecules form chains running along the b axis through N-H⋯O hydrogen bonds.

Related literature

For related structures, see: Gowda et al. (2003 ▶, 2008a ▶,b ▶); Gowda, Tokarčík et al. (2008 ▶).

Experimental

Crystal data

C14H12ClNO

M = 245.70

Monoclinic,

a = 22.345 (2) Å

b = 5.1092 (4) Å

c = 22.222 (1) Å

β = 109.593 (6)°

V = 2390.1 (3) Å3

Z = 8

Cu Kα radiation

μ = 2.67 mm−1

T = 299 (2) K

0.50 × 0.13 × 0.13 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

2213 measured reflections

2085 independent reflections

1741 reflections with I > 2σ(I)

R int = 0.074

3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.159

S = 1.08

2085 reflections

182 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.39 e Å−3

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC; 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/S1600536809002633/bt2857sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002633/bt2857Isup2.hkl

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

C14H12ClNO	F(000) = 1024
Mr = 245.70	Dx = 1.366 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 22.345 (2) Å	θ = 8.1–22.2°
b = 5.1092 (4) Å	µ = 2.67 mm−1
c = 22.222 (1) Å	T = 299 K
β = 109.593 (6)°	Rod, colourless
V = 2390.1 (3) Å3	0.50 × 0.13 × 0.13 mm
Z = 8

Enraf–Nonius CAD-4 diffractometer	Rint = 0.074
Radiation source: fine-focus sealed tube	θmax = 66.9°, θmin = 4.2°
graphite	h = −25→26
ω/2θ scans	k = −6→0
2213 measured reflections	l = −26→1
2085 independent reflections	3 standard reflections every 120 min
1741 reflections with I > 2σ(I)	intensity decay: 1.0%

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)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.159	w = 1/[σ2(Fo2) + (0.1089P)2 + 0.7738P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.002
2085 reflections	Δρmax = 0.27 e Å−3
182 parameters	Δρmin = −0.39 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0012 (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	0.38579 (10)	−0.0174 (4)	0.97284 (10)	0.0427 (5)
C2	0.43053 (12)	−0.1978 (5)	0.96925 (11)	0.0531 (6)
H2	0.4467 (13)	−0.343 (6)	1.0021 (12)	0.064*
C3	0.45905 (12)	−0.1751 (6)	0.92298 (12)	0.0582 (6)
H3	0.4906 (14)	−0.296 (6)	0.9225 (13)	0.070*
C4	0.44190 (11)	0.0270 (5)	0.88024 (10)	0.0501 (6)
C5	0.39547 (13)	0.2001 (5)	0.88127 (11)	0.0556 (6)
H5	0.3833 (13)	0.344 (7)	0.8502 (13)	0.067*
C6	0.36711 (12)	0.1774 (5)	0.92743 (10)	0.0541 (6)
H6	0.3328 (14)	0.277 (6)	0.9283 (12)	0.065*
C7	0.34840 (11)	0.1669 (4)	1.05601 (10)	0.0464 (5)
C8	0.32646 (10)	0.0953 (4)	1.11029 (10)	0.0422 (5)
C9	0.35181 (9)	0.2246 (4)	1.16938 (9)	0.0437 (5)
C10	0.32915 (11)	0.1468 (5)	1.21792 (11)	0.0529 (6)
H10	0.3491 (12)	0.242 (6)	1.2606 (13)	0.063*
C11	0.28353 (12)	−0.0416 (5)	1.20908 (12)	0.0573 (6)
H11	0.2695 (14)	−0.099 (6)	1.2430 (14)	0.069*
C12	0.25847 (11)	−0.1652 (5)	1.15110 (12)	0.0567 (6)
H12	0.2257 (13)	−0.308 (6)	1.1438 (12)	0.068*
C13	0.28029 (11)	−0.0955 (5)	1.10188 (11)	0.0497 (5)
H13	0.2621 (12)	−0.182 (6)	1.0597 (12)	0.060*
C14	0.40270 (12)	0.4269 (5)	1.18350 (12)	0.0570 (6)
H14A	0.4283	0.4180	1.2278	0.068*
H14B	0.3837	0.5973	1.1741	0.068*
H14C	0.4288	0.3958	1.1576	0.068*
N1	0.36006 (10)	−0.0392 (4)	1.02268 (8)	0.0461 (5)
H1N	0.3609 (12)	−0.189 (6)	1.0382 (12)	0.055*
O1	0.35554 (12)	0.3935 (3)	1.04201 (9)	0.0740 (6)
Cl1	0.48134 (3)	0.07146 (16)	0.82524 (3)	0.0760 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0526 (11)	0.0351 (10)	0.0411 (10)	−0.0047 (9)	0.0164 (9)	−0.0033 (8)
C2	0.0640 (13)	0.0443 (13)	0.0541 (12)	0.0073 (10)	0.0240 (10)	0.0077 (10)
C3	0.0597 (13)	0.0582 (15)	0.0617 (14)	0.0086 (11)	0.0270 (11)	0.0013 (12)
C4	0.0588 (12)	0.0507 (13)	0.0445 (11)	−0.0110 (10)	0.0220 (10)	−0.0055 (9)
C5	0.0773 (15)	0.0458 (14)	0.0448 (11)	0.0035 (11)	0.0220 (10)	0.0053 (10)
C6	0.0688 (14)	0.0485 (14)	0.0479 (12)	0.0123 (11)	0.0233 (10)	0.0040 (10)
C7	0.0638 (12)	0.0334 (11)	0.0459 (11)	0.0005 (9)	0.0234 (9)	0.0011 (8)
C8	0.0485 (10)	0.0354 (11)	0.0447 (10)	0.0052 (8)	0.0185 (8)	0.0017 (8)
C9	0.0458 (10)	0.0394 (11)	0.0479 (11)	0.0053 (8)	0.0184 (8)	0.0003 (8)
C10	0.0592 (13)	0.0557 (14)	0.0485 (11)	0.0053 (11)	0.0245 (10)	−0.0031 (10)
C11	0.0628 (14)	0.0616 (15)	0.0590 (13)	0.0013 (11)	0.0358 (12)	0.0055 (11)
C12	0.0522 (12)	0.0537 (14)	0.0695 (15)	−0.0074 (11)	0.0274 (11)	0.0023 (12)
C13	0.0513 (11)	0.0461 (13)	0.0505 (11)	−0.0004 (10)	0.0155 (9)	0.0001 (10)
C14	0.0600 (13)	0.0505 (15)	0.0621 (13)	−0.0057 (10)	0.0226 (11)	−0.0080 (10)
N1	0.0669 (11)	0.0315 (9)	0.0455 (10)	0.0002 (8)	0.0262 (8)	0.0018 (7)
O1	0.1407 (18)	0.0319 (9)	0.0708 (11)	−0.0004 (10)	0.0636 (12)	0.0022 (7)
Cl1	0.0838 (5)	0.0892 (6)	0.0706 (5)	−0.0083 (4)	0.0465 (4)	0.0039 (4)

C1—C6	1.378 (3)	C8—C13	1.386 (3)
C1—C2	1.382 (3)	C8—C9	1.408 (3)
C1—N1	1.413 (3)	C9—C10	1.394 (3)
C2—C3	1.384 (3)	C9—C14	1.490 (3)
C2—H2	1.02 (3)	C10—C11	1.368 (4)
C3—C4	1.368 (4)	C10—H10	1.03 (3)
C3—H3	0.94 (3)	C11—C12	1.374 (4)
C4—C5	1.369 (4)	C11—H11	0.95 (3)
C4—Cl1	1.745 (2)	C12—C13	1.385 (3)
C5—C6	1.380 (3)	C12—H12	1.01 (3)
C5—H5	0.98 (3)	C13—H13	0.99 (3)
C6—H6	0.93 (3)	C14—H14A	0.9600
C7—O1	1.223 (3)	C14—H14B	0.9600
C7—N1	1.362 (3)	C14—H14C	0.9600
C7—C8	1.492 (3)	N1—H1N	0.84 (3)
C6—C1—C2	119.1 (2)	C10—C9—C8	116.8 (2)
C6—C1—N1	121.9 (2)	C10—C9—C14	119.0 (2)
C2—C1—N1	119.03 (19)	C8—C9—C14	124.18 (19)
C1—C2—C3	120.6 (2)	C11—C10—C9	122.4 (2)
C1—C2—H2	122.3 (15)	C11—C10—H10	122.6 (16)
C3—C2—H2	116.9 (15)	C9—C10—H10	115.0 (16)
C4—C3—C2	119.2 (2)	C10—C11—C12	120.5 (2)
C4—C3—H3	121.7 (17)	C10—C11—H11	122.0 (18)
C2—C3—H3	119.1 (17)	C12—C11—H11	117.4 (19)
C3—C4—C5	120.9 (2)	C11—C12—C13	118.8 (2)
C3—C4—Cl1	119.67 (19)	C11—C12—H12	122.0 (15)
C5—C4—Cl1	119.40 (19)	C13—C12—H12	119.2 (15)
C4—C5—C6	119.8 (2)	C12—C13—C8	121.2 (2)
C4—C5—H5	120.3 (17)	C12—C13—H13	119.4 (16)
C6—C5—H5	119.8 (17)	C8—C13—H13	119.4 (16)
C1—C6—C5	120.2 (2)	C9—C14—H14A	109.5
C1—C6—H6	115.6 (17)	C9—C14—H14B	109.5
C5—C6—H6	124.0 (17)	H14A—C14—H14B	109.5
O1—C7—N1	121.9 (2)	C9—C14—H14C	109.5
O1—C7—C8	122.95 (19)	H14A—C14—H14C	109.5
N1—C7—C8	115.14 (19)	H14B—C14—H14C	109.5
C13—C8—C9	120.3 (2)	C7—N1—C1	124.59 (19)
C13—C8—C7	119.68 (19)	C7—N1—H1N	117.7 (18)
C9—C8—C7	120.03 (19)	C1—N1—H1N	115.8 (18)
C6—C1—C2—C3	3.7 (4)	C7—C8—C9—C10	−179.84 (19)
N1—C1—C2—C3	−176.8 (2)	C13—C8—C9—C14	178.3 (2)
C1—C2—C3—C4	−0.7 (4)	C7—C8—C9—C14	−2.8 (3)
C2—C3—C4—C5	−2.4 (4)	C8—C9—C10—C11	−1.4 (3)
C2—C3—C4—Cl1	175.54 (19)	C14—C9—C10—C11	−178.6 (2)
C3—C4—C5—C6	2.5 (4)	C9—C10—C11—C12	0.7 (4)
Cl1—C4—C5—C6	−175.48 (19)	C10—C11—C12—C13	0.0 (4)
C2—C1—C6—C5	−3.7 (4)	C11—C12—C13—C8	−0.1 (4)
N1—C1—C6—C5	176.9 (2)	C9—C8—C13—C12	−0.6 (3)
C4—C5—C6—C1	0.6 (4)	C7—C8—C13—C12	−179.5 (2)
O1—C7—C8—C13	135.1 (3)	O1—C7—N1—C1	5.2 (4)
N1—C7—C8—C13	−44.8 (3)	C8—C7—N1—C1	−174.86 (18)
O1—C7—C8—C9	−43.7 (3)	C6—C1—N1—C7	−41.2 (3)
N1—C7—C8—C9	136.3 (2)	C2—C1—N1—C7	139.3 (2)
C13—C8—C9—C10	1.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.84 (3)	2.14 (3)	2.937 (3)	159 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.84 (3)	2.14 (3)	2.937 (3)	159 (2)

Symmetry code: (i) .