N-(4-Chloro-phen-yl)-3-methyl-benzamide.

In the structure of the title compound, C(14)H(12)ClNO, the conformations of the N-H and C=O bonds are anti to each other. Furthermore, the conformation of the C=O bond is syn to the meta-methyl group in the benzoyl ring. The central -NH-C(=O)- amido group makes a dihedral angle of 32.4 (1)° with the benzoyl ring and 36.1 (1)° with the anilino ring. The dihedral angle between the two benzene rings is 68.4 (1)°. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into chains running along the a axis.

Related literature

For the preparation of the title compound, see: Gowda et al. (2003 ▶). For related structures, see: Bowes et al. (2003 ▶); Gowda, Foro et al. (2008 ▶, 2009 ▶); Gowda, Tokarčík et al. (2008 ▶).

Experimental

Crystal data

C14H12ClNO

M = 245.7

Monoclinic,

a = 5.31325 (9) Å

b = 13.9256 (2) Å

c = 16.3497 (3) Å

β = 93.1799 (16)°

V = 1207.86 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 295 K

0.54 × 0.41 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur, Ruby, Gemini diffractometer

Absorption correction: analytical (CrysAlisPro; Oxford Diffraction, 2009 ▶) T min = 0.842, T max = 0.933

22561 measured reflections

2327 independent reflections

2083 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.093

S = 1.08

2327 reflections

160 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlisPro (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlisPro; data reduction: CrysAlisPro; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2002 ▶); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536809041956/om2285sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041956/om2285Isup2.hkl

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

C14H12ClNO	F(000) = 512
Mr = 245.7	Dx = 1.351 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 15854 reflections
a = 5.31325 (9) Å	θ = 2.5–29.5°
b = 13.9256 (2) Å	µ = 0.30 mm−1
c = 16.3497 (3) Å	T = 295 K
β = 93.1799 (16)°	Block, colourless
V = 1207.86 (3) Å3	0.54 × 0.41 × 0.24 mm
Z = 4

Oxford Diffraction Xcalibur, Ruby, Gemini diffractometer	2327 independent reflections
graphite	2083 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1	Rint = 0.021
ω scans	θmax = 25.8°, θmin = 2.5°
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	h = −6→6
Tmin = 0.842, Tmax = 0.933	k = −17→17
22561 measured reflections	l = −19→19

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)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.093	w = 1/[σ2(Fo2) + (0.0428P)2 + 0.3304P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
2327 reflections	Δρmax = 0.20 e Å−3
160 parameters	Δρmin = −0.25 e Å−3
1 restraint	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0092 (14)

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	Occ. (<1)
N1	0.1646 (2)	0.45549 (8)	0.39171 (8)	0.0412 (3)
H1N	0.017 (3)	0.4290 (12)	0.3885 (10)	0.049*
O1	0.58424 (19)	0.42883 (8)	0.38537 (8)	0.0557 (3)
C1	0.3719 (2)	0.39844 (10)	0.39515 (8)	0.0386 (3)
C2	0.3269 (2)	0.29460 (10)	0.41211 (8)	0.0369 (3)
C3	0.4867 (3)	0.22789 (10)	0.37862 (9)	0.0405 (3)
H3	0.6157	0.2493	0.347	0.049*
C4	0.4574 (3)	0.13000 (10)	0.39146 (9)	0.0431 (3)
C5	0.2706 (3)	0.10059 (11)	0.44192 (10)	0.0498 (4)
H5	0.2506	0.0355	0.4525	0.06*
C6	0.1136 (3)	0.16637 (12)	0.47667 (10)	0.0522 (4)
H6	−0.0093	0.1451	0.5108	0.063*
C7	0.1374 (3)	0.26343 (11)	0.46128 (9)	0.0437 (3)
H7	0.0283	0.3073	0.4835	0.052*
C8	0.1610 (2)	0.55455 (10)	0.37157 (8)	0.0366 (3)
C9	0.3518 (3)	0.61698 (11)	0.39831 (9)	0.0443 (3)
H9	0.4893	0.5941	0.4302	0.053*
C10	0.3380 (3)	0.71322 (11)	0.37762 (10)	0.0482 (4)
H10	0.4658	0.7551	0.3955	0.058*
C11	0.1347 (3)	0.74660 (11)	0.33054 (9)	0.0447 (4)
C12	−0.0573 (3)	0.68588 (11)	0.30389 (10)	0.0489 (4)
H12	−0.1946	0.7093	0.2722	0.059*
C13	−0.0436 (3)	0.58985 (11)	0.32472 (9)	0.0449 (3)
H13	−0.173	0.5485	0.3071	0.054*
C14	0.6205 (3)	0.05784 (13)	0.35038 (12)	0.0605 (4)
H14A	0.7546	0.0907	0.325	0.091*	0.5
H14B	0.5204	0.0233	0.3095	0.091*	0.5
H14C	0.6904	0.0136	0.3905	0.091*	0.5
H14D	0.5557	−0.0056	0.3583	0.091*	0.5
H14E	0.7899	0.0617	0.3738	0.091*	0.5
H14F	0.6198	0.0715	0.2928	0.091*	0.5
Cl1	0.11527 (11)	0.86780 (3)	0.30416 (3)	0.07259 (19)

	U11	U22	U33	U12	U13	U23
N1	0.0333 (6)	0.0357 (6)	0.0548 (7)	−0.0041 (5)	0.0028 (5)	0.0011 (5)
O1	0.0374 (5)	0.0426 (6)	0.0884 (9)	−0.0029 (4)	0.0141 (5)	0.0086 (6)
C1	0.0371 (7)	0.0378 (7)	0.0413 (7)	−0.0025 (6)	0.0052 (5)	0.0010 (6)
C2	0.0345 (6)	0.0381 (7)	0.0377 (7)	−0.0030 (5)	−0.0016 (5)	0.0008 (6)
C3	0.0355 (7)	0.0430 (8)	0.0429 (7)	−0.0015 (6)	0.0028 (6)	0.0010 (6)
C4	0.0418 (7)	0.0402 (8)	0.0465 (8)	0.0014 (6)	−0.0052 (6)	−0.0025 (6)
C5	0.0538 (9)	0.0363 (8)	0.0589 (9)	−0.0057 (7)	−0.0005 (7)	0.0045 (7)
C6	0.0524 (9)	0.0478 (9)	0.0577 (9)	−0.0102 (7)	0.0146 (7)	0.0050 (7)
C7	0.0409 (7)	0.0420 (8)	0.0490 (8)	−0.0025 (6)	0.0093 (6)	−0.0008 (6)
C8	0.0355 (7)	0.0354 (7)	0.0393 (7)	−0.0015 (5)	0.0068 (5)	−0.0012 (5)
C9	0.0390 (7)	0.0420 (8)	0.0511 (8)	0.0002 (6)	−0.0043 (6)	−0.0048 (6)
C10	0.0449 (8)	0.0397 (8)	0.0600 (9)	−0.0089 (6)	0.0028 (7)	−0.0082 (7)
C11	0.0532 (9)	0.0361 (7)	0.0460 (8)	−0.0013 (6)	0.0133 (7)	0.0022 (6)
C12	0.0464 (8)	0.0474 (8)	0.0523 (9)	0.0027 (7)	−0.0026 (7)	0.0074 (7)
C13	0.0373 (7)	0.0428 (8)	0.0540 (9)	−0.0059 (6)	−0.0019 (6)	0.0007 (7)
C14	0.0588 (10)	0.0486 (9)	0.0743 (12)	0.0070 (8)	0.0055 (8)	−0.0091 (8)
Cl1	0.0979 (4)	0.0399 (2)	0.0805 (3)	−0.0026 (2)	0.0090 (3)	0.0145 (2)

N1—C1	1.3565 (18)	C8—C9	1.388 (2)
N1—C8	1.4181 (18)	C9—C10	1.383 (2)
N1—H1N	0.864 (14)	C9—H9	0.93
O1—C1	1.2239 (17)	C10—C11	1.372 (2)
C1—C2	1.4942 (19)	C10—H10	0.93
C2—C3	1.391 (2)	C11—C12	1.377 (2)
C2—C7	1.3922 (19)	C11—Cl1	1.7437 (15)
C3—C4	1.389 (2)	C12—C13	1.381 (2)
C3—H3	0.93	C12—H12	0.93
C4—C5	1.387 (2)	C13—H13	0.93
C4—C14	1.509 (2)	C14—H14A	0.96
C5—C6	1.382 (2)	C14—H14B	0.96
C5—H5	0.93	C14—H14C	0.96
C6—C7	1.382 (2)	C14—H14D	0.96
C6—H6	0.93	C14—H14E	0.96
C7—H7	0.93	C14—H14F	0.96
C8—C13	1.385 (2)
C1—N1—C8	125.43 (12)	C9—C10—H10	120.2
C1—N1—H1N	118.9 (11)	C10—C11—C12	121.04 (14)
C8—N1—H1N	113.6 (11)	C10—C11—Cl1	120.05 (12)
O1—C1—N1	122.98 (13)	C12—C11—Cl1	118.91 (12)
O1—C1—C2	121.13 (12)	C11—C12—C13	119.25 (14)
N1—C1—C2	115.89 (12)	C11—C12—H12	120.4
C3—C2—C7	119.73 (13)	C13—C12—H12	120.4
C3—C2—C1	117.77 (12)	C12—C13—C8	120.61 (13)
C7—C2—C1	122.49 (13)	C12—C13—H13	119.7
C4—C3—C2	121.34 (13)	C8—C13—H13	119.7
C4—C3—H3	119.3	C4—C14—H14A	109.5
C2—C3—H3	119.3	C4—C14—H14B	109.5
C5—C4—C3	117.98 (14)	H14A—C14—H14B	109.5
C5—C4—C14	121.05 (14)	C4—C14—H14C	109.5
C3—C4—C14	120.96 (14)	H14A—C14—H14C	109.5
C6—C5—C4	121.12 (14)	H14B—C14—H14C	109.5
C6—C5—H5	119.4	C4—C14—H14D	109.5
C4—C5—H5	119.4	H14A—C14—H14D	141.1
C7—C6—C5	120.66 (14)	H14B—C14—H14D	56.3
C7—C6—H6	119.7	H14C—C14—H14D	56.3
C5—C6—H6	119.7	C4—C14—H14E	109.5
C6—C7—C2	119.11 (14)	H14A—C14—H14E	56.3
C6—C7—H7	120.4	H14B—C14—H14E	141.1
C2—C7—H7	120.4	H14C—C14—H14E	56.3
C13—C8—C9	119.29 (13)	H14D—C14—H14E	109.5
C13—C8—N1	118.28 (12)	C4—C14—H14F	109.5
C9—C8—N1	122.42 (13)	H14A—C14—H14F	56.3
C10—C9—C8	120.13 (14)	H14B—C14—H14F	56.3
C10—C9—H9	119.9	H14C—C14—H14F	141.1
C8—C9—H9	119.9	H14D—C14—H14F	109.5
C11—C10—C9	119.67 (13)	H14E—C14—H14F	109.5
C11—C10—H10	120.2
C8—N1—C1—O1	4.3 (2)	C3—C2—C7—C6	0.7 (2)
C8—N1—C1—C2	−175.93 (12)	C1—C2—C7—C6	−177.55 (14)
O1—C1—C2—C3	−31.1 (2)	C1—N1—C8—C13	142.17 (15)
N1—C1—C2—C3	149.10 (13)	C1—N1—C8—C9	−39.0 (2)
O1—C1—C2—C7	147.24 (15)	C13—C8—C9—C10	−0.6 (2)
N1—C1—C2—C7	−32.57 (19)	N1—C8—C9—C10	−179.33 (14)
C7—C2—C3—C4	1.7 (2)	C8—C9—C10—C11	0.0 (2)
C1—C2—C3—C4	−179.96 (13)	C9—C10—C11—C12	0.5 (2)
C2—C3—C4—C5	−2.9 (2)	C9—C10—C11—Cl1	179.97 (12)
C2—C3—C4—C14	175.93 (14)	C10—C11—C12—C13	−0.3 (2)
C3—C4—C5—C6	1.7 (2)	Cl1—C11—C12—C13	−179.82 (12)
C14—C4—C5—C6	−177.08 (15)	C11—C12—C13—C8	−0.3 (2)
C4—C5—C6—C7	0.6 (3)	C9—C8—C13—C12	0.7 (2)
C5—C6—C7—C2	−1.9 (2)	N1—C8—C13—C12	179.54 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.86 (1)	2.30 (1)	3.1019 (16)	155 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.864 (14)	2.298 (14)	3.1019 (16)	154.7 (15)

Symmetry code: (i) .