4-Chloro-N-m-tolyl-benzamide.

In the title compound, C(14)H(12)ClNO, the dihedral angle between the two aromatic rings is 11.29 (15)°. The crystal packing is stabilized by N-H⋯O hydrogen bonds linking the mol-ecules into chains running along the c axis.

Related literature

For the biological activity of N-substituted benzamides and benzanilide derivatives, see Calderone et al. (2006 ▶); Beccalli et al. (2005 ▶); Yoo et al. (2005 ▶); Vega-Noverola et al. (1989 ▶); Olsson et al. (2002 ▶); Lindgren et al. (2001 ▶); Zhichkin et al. (2007 ▶). For related structures see: Saeed et al. (2008 ▶); Chopra & Guru Row (2008 ▶); Donnelly et al. (2008 ▶)

Experimental

Crystal data

C14H12ClNO

M = 245.70

Monoclinic,

a = 13.9721 (14) Å

b = 10.1922 (6) Å

c = 9.0154 (8) Å

β = 105.415 (7)°

V = 1237.67 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 173 K

0.26 × 0.24 × 0.23 mm

Data collection

Stoe IPDSII two-circle diffractometer

Absorption correction: multi-scan (MULABS; Spek, 2009 ▶; Blessing, 1995 ▶) T min = 0.928, T max = 0.936

9469 measured reflections

2193 independent reflections

1787 reflections with I > 2σ(I)

R int = 0.074

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.178

S = 1.04

2193 reflections

160 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.51 e Å−3

Δρmin = −0.47 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; 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 datablocks global, I. DOI: 10.1107/S1600536809018236/ya2096sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018236/ya2096Isup2.hkl

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

C14H12ClNO	F(000) = 512
Mr = 245.70	Dx = 1.319 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10353 reflections
a = 13.9721 (14) Å	θ = 2.6–27.8°
b = 10.1922 (6) Å	µ = 0.29 mm−1
c = 9.0154 (8) Å	T = 173 K
β = 105.415 (7)°	Block, colourless
V = 1237.67 (18) Å3	0.26 × 0.24 × 0.23 mm
Z = 4

Stoe IPDSII two-circle diffractometer	2193 independent reflections
Radiation source: fine-focus sealed tube	1787 reflections with I > 2σ(I)
graphite	Rint = 0.074
ω scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	h = −16→16
Tmin = 0.928, Tmax = 0.936	k = −12→12
9469 measured reflections	l = −10→10

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)] = 0.066	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.178	w = 1/[σ2(Fo2) + (0.1231P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2193 reflections	Δρmax = 0.51 e Å−3
160 parameters	Δρmin = −0.47 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: 0.018 (5)

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
Cl1	0.86033 (5)	0.92615 (6)	0.74007 (9)	0.0588 (3)
O1	0.41731 (13)	0.85570 (16)	0.23364 (18)	0.0439 (5)
N1	0.38823 (16)	0.72470 (18)	0.4215 (2)	0.0393 (5)
H1	0.408 (2)	0.702 (2)	0.519 (3)	0.041 (7)*
C1	0.44505 (17)	0.80750 (19)	0.3639 (3)	0.0366 (5)
C11	0.54665 (18)	0.83650 (19)	0.4646 (3)	0.0371 (6)
C12	0.59229 (19)	0.7638 (2)	0.5951 (3)	0.0435 (6)
H12	0.5574	0.6930	0.6253	0.052*
C13	0.68742 (19)	0.7929 (2)	0.6814 (3)	0.0456 (6)
H13	0.7172	0.7434	0.7711	0.055*
C14	0.73903 (18)	0.8948 (2)	0.6362 (3)	0.0422 (6)
C15	0.69544 (19)	0.9691 (2)	0.5060 (3)	0.0413 (6)
H15	0.7311	1.0387	0.4753	0.050*
C16	0.6000 (2)	0.94034 (19)	0.4222 (3)	0.0398 (6)
H16	0.5697	0.9917	0.3343	0.048*
C21	0.29378 (19)	0.6714 (2)	0.3444 (3)	0.0388 (6)
C22	0.22613 (19)	0.7341 (2)	0.2241 (3)	0.0404 (6)
H22	0.2426	0.8166	0.1884	0.049*
C23	0.13421 (19)	0.6770 (2)	0.1555 (3)	0.0429 (6)
C24	0.1115 (2)	0.5552 (2)	0.2080 (3)	0.0468 (6)
H24	0.0499	0.5142	0.1605	0.056*
C25	0.1784 (2)	0.4941 (2)	0.3291 (3)	0.0488 (6)
H25	0.1618	0.4118	0.3651	0.059*
C26	0.2693 (2)	0.5508 (2)	0.3988 (3)	0.0452 (6)
H26	0.3145	0.5084	0.4826	0.054*
C27	0.0604 (2)	0.7461 (3)	0.0252 (3)	0.0561 (7)
H27A	0.0720	0.7202	−0.0732	0.084*
H27B	0.0686	0.8413	0.0383	0.084*
H27C	−0.0073	0.7216	0.0264	0.084*

	U11	U22	U33	U12	U13	U23
Cl1	0.0465 (5)	0.0523 (5)	0.0671 (6)	−0.0050 (3)	−0.0031 (4)	−0.0004 (3)
O1	0.0528 (11)	0.0441 (9)	0.0317 (9)	−0.0007 (7)	0.0059 (8)	0.0023 (7)
N1	0.0477 (12)	0.0352 (9)	0.0296 (11)	−0.0020 (8)	0.0009 (9)	0.0012 (8)
C1	0.0479 (14)	0.0276 (10)	0.0321 (12)	0.0042 (9)	0.0067 (10)	−0.0024 (8)
C11	0.0481 (14)	0.0277 (10)	0.0340 (12)	0.0040 (9)	0.0081 (11)	−0.0020 (8)
C12	0.0481 (15)	0.0363 (11)	0.0433 (14)	−0.0019 (10)	0.0070 (12)	0.0059 (10)
C13	0.0485 (15)	0.0391 (12)	0.0435 (14)	0.0040 (11)	0.0021 (12)	0.0106 (10)
C14	0.0441 (14)	0.0334 (11)	0.0458 (14)	0.0025 (10)	0.0062 (12)	−0.0051 (10)
C15	0.0522 (14)	0.0306 (11)	0.0409 (13)	−0.0014 (10)	0.0119 (12)	−0.0010 (9)
C16	0.0539 (15)	0.0283 (10)	0.0345 (13)	0.0020 (9)	0.0070 (11)	−0.0005 (9)
C21	0.0468 (13)	0.0322 (11)	0.0343 (12)	−0.0028 (9)	0.0053 (11)	−0.0059 (9)
C22	0.0487 (14)	0.0343 (11)	0.0358 (13)	−0.0011 (9)	0.0069 (11)	−0.0032 (9)
C23	0.0471 (14)	0.0448 (13)	0.0350 (13)	−0.0002 (10)	0.0080 (11)	−0.0066 (10)
C24	0.0490 (15)	0.0410 (12)	0.0478 (15)	−0.0060 (10)	0.0081 (12)	−0.0116 (10)
C25	0.0566 (15)	0.0357 (12)	0.0523 (15)	−0.0047 (11)	0.0111 (13)	−0.0041 (10)
C26	0.0546 (16)	0.0336 (11)	0.0432 (14)	−0.0011 (10)	0.0058 (12)	−0.0013 (9)
C27	0.0510 (17)	0.0587 (15)	0.0500 (16)	−0.0056 (12)	−0.0017 (13)	0.0034 (12)

Cl1—C14	1.734 (3)	C16—H16	0.9500
O1—C1	1.236 (3)	C21—C22	1.390 (3)
N1—C1	1.353 (3)	C21—C26	1.398 (3)
N1—C21	1.426 (3)	C22—C23	1.396 (3)
N1—H1	0.88 (3)	C22—H22	0.9500
C1—C11	1.497 (3)	C23—C24	1.394 (3)
C11—C12	1.393 (3)	C23—C27	1.515 (4)
C11—C16	1.404 (3)	C24—C25	1.383 (4)
C12—C13	1.382 (4)	C24—H24	0.9500
C12—H12	0.9500	C25—C26	1.385 (4)
C13—C14	1.386 (4)	C25—H25	0.9500
C13—H13	0.9500	C26—H26	0.9500
C14—C15	1.393 (3)	C27—H27A	0.9800
C15—C16	1.378 (4)	C27—H27B	0.9800
C15—H15	0.9500	C27—H27C	0.9800
C1—N1—C21	127.7 (2)	C22—C21—C26	119.9 (2)
C1—N1—H1	119.2 (18)	C22—C21—N1	123.7 (2)
C21—N1—H1	112.9 (18)	C26—C21—N1	116.4 (2)
O1—C1—N1	123.0 (2)	C21—C22—C23	120.6 (2)
O1—C1—C11	120.3 (2)	C21—C22—H22	119.7
N1—C1—C11	116.7 (2)	C23—C22—H22	119.7
C12—C11—C16	118.3 (2)	C24—C23—C22	119.1 (2)
C12—C11—C1	123.7 (2)	C24—C23—C27	120.5 (2)
C16—C11—C1	118.0 (2)	C22—C23—C27	120.4 (2)
C13—C12—C11	121.1 (2)	C25—C24—C23	120.1 (2)
C13—C12—H12	119.4	C25—C24—H24	119.9
C11—C12—H12	119.4	C23—C24—H24	119.9
C12—C13—C14	119.5 (2)	C24—C25—C26	121.1 (2)
C12—C13—H13	120.2	C24—C25—H25	119.5
C14—C13—H13	120.2	C26—C25—H25	119.5
C13—C14—C15	120.6 (2)	C25—C26—C21	119.2 (2)
C13—C14—Cl1	119.28 (19)	C25—C26—H26	120.4
C15—C14—Cl1	120.04 (19)	C21—C26—H26	120.4
C16—C15—C14	119.3 (2)	C23—C27—H27A	109.5
C16—C15—H15	120.4	C23—C27—H27B	109.5
C14—C15—H15	120.4	H27A—C27—H27B	109.5
C15—C16—C11	121.2 (2)	C23—C27—H27C	109.5
C15—C16—H16	119.4	H27A—C27—H27C	109.5
C11—C16—H16	119.4	H27B—C27—H27C	109.5
C21—N1—C1—O1	5.0 (4)	C12—C11—C16—C15	0.8 (3)
C21—N1—C1—C11	−173.24 (19)	C1—C11—C16—C15	−177.3 (2)
O1—C1—C11—C12	−164.2 (2)	C1—N1—C21—C22	−28.5 (4)
N1—C1—C11—C12	14.2 (3)	C1—N1—C21—C26	153.4 (2)
O1—C1—C11—C16	13.8 (3)	C26—C21—C22—C23	−0.9 (4)
N1—C1—C11—C16	−167.84 (19)	N1—C21—C22—C23	−179.0 (2)
C16—C11—C12—C13	0.2 (4)	C21—C22—C23—C24	−0.7 (4)
C1—C11—C12—C13	178.2 (2)	C21—C22—C23—C27	179.5 (2)
C11—C12—C13—C14	−1.0 (4)	C22—C23—C24—C25	1.6 (4)
C12—C13—C14—C15	0.9 (4)	C27—C23—C24—C25	−178.6 (3)
C12—C13—C14—Cl1	−177.17 (19)	C23—C24—C25—C26	−1.0 (4)
C13—C14—C15—C16	0.1 (4)	C24—C25—C26—C21	−0.6 (4)
Cl1—C14—C15—C16	178.14 (18)	C22—C21—C26—C25	1.5 (4)
C14—C15—C16—C11	−1.0 (4)	N1—C21—C26—C25	179.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.88 (3)	1.99 (3)	2.854 (3)	166 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.88 (3)	1.99 (3)	2.854 (3)	166 (3)

Symmetry code: (i) .