4-Chloro-N-o-tolyl-benzamide.

In the mol-ecule of the title compound, C(14)H(12)ClNO, the two benzene rings are close to coplanar [dihedral angle = 7.85 (4)°]. The amide N-C=O plane makes dihedral angles of 34.04 (4) and 39.90 (3)°, respectively, with the 4-chloro- and 2-methyl-phenyl rings. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into chains.

Related literature

For a related structure, see: Saeed et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H12ClNO

M = 245.71

Monoclinic,

a = 10.7906 (14) Å

b = 4.8793 (6) Å

c = 23.522 (3) Å

β = 98.125 (3)°

V = 1226.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 223 (1) K

0.40 × 0.18 × 0.09 mm

Data collection

Rigaku R-AXIS RAPID II diffractometer

Absorption correction: numerical (ABSCOR; Higashi, 1999 ▶) T min = 0.928, T max = 0.974

14142 measured reflections

3461 independent reflections

1685 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.166

S = 1.06

3461 reflections

159 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.28 e Å−3

Data collection: PROCESS-AUTO (Rigaku/MSC, 2004 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); 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 PLATON (Spek, 2003 ▶); software used to prepare material for publication: CrystalStructure and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808030912/hk2536sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030912/hk2536Isup2.hkl

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

C14H12ClNO	F(000) = 512.00
Mr = 245.71	Dx = 1.331 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2yn	Cell parameters from 7779 reflections
a = 10.7906 (14) Å	θ = 3.0–30.0°
b = 4.8793 (6) Å	µ = 0.29 mm−1
c = 23.522 (3) Å	T = 223 K
β = 98.125 (3)°	Block, colorless
V = 1226.0 (3) Å3	0.40 × 0.18 × 0.09 mm
Z = 4

Rigaku R-AXIS RAPID II diffractometer	1685 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm-1	Rint = 0.046
ω scans	θmax = 30.0°, θmin = 3.0°
Absorption correction: numerical (ABSCOR; Higashi, 1999)	h = −15→15
Tmin = 0.928, Tmax = 0.974	k = −6→6
14142 measured reflections	l = −33→33
3461 independent reflections

Refinement on F2	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.049	w = 1/[σ2(Fo2) + (0.0782P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.166	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.22 e Å−3
3461 reflections	Δρmin = −0.28 e Å−3
159 parameters

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)
Cl1	0.40808 (7)	0.32489 (17)	0.27042 (3)	0.1042 (3)
O1	0.31241 (13)	0.9179 (2)	0.51539 (6)	0.0709 (4)
N1	0.25683 (14)	0.4881 (3)	0.53727 (6)	0.0523 (4)
H1	0.2591 (18)	0.319 (4)	0.5268 (8)	0.067 (6)*
C1	0.32795 (16)	0.5743 (3)	0.44582 (8)	0.0509 (4)
C2	0.42185 (17)	0.7014 (4)	0.42126 (10)	0.0653 (5)
H2	0.4689	0.8416	0.4414	0.078*
C3	0.4477 (2)	0.6259 (4)	0.36758 (10)	0.0750 (6)
H3	0.5129	0.7107	0.3515	0.090*
C4	0.3762 (2)	0.4243 (4)	0.33802 (9)	0.0676 (5)
C5	0.2816 (2)	0.2953 (4)	0.36098 (9)	0.0686 (5)
H5	0.2336	0.1583	0.3402	0.082*
C6	0.25799 (18)	0.3701 (4)	0.41517 (8)	0.0600 (5)
H6	0.1940	0.2817	0.4314	0.072*
C7	0.29972 (15)	0.6742 (3)	0.50259 (8)	0.0496 (4)
C8	0.21114 (17)	0.5490 (3)	0.58983 (7)	0.0520 (4)
C9	0.10277 (18)	0.4181 (4)	0.60191 (8)	0.0579 (5)
C10	0.0587 (2)	0.4874 (5)	0.65275 (9)	0.0779 (6)
H10	−0.0138	0.4006	0.6618	0.093*
C11	0.1170 (3)	0.6773 (6)	0.68999 (10)	0.0923 (8)
H11	0.0837	0.7228	0.7236	0.111*
C12	0.2238 (3)	0.8005 (5)	0.67811 (10)	0.0905 (8)
H12	0.2645	0.9300	0.7038	0.109*
C13	0.2728 (2)	0.7363 (4)	0.62834 (9)	0.0700 (6)
H13	0.3473	0.8191	0.6207	0.084*
C14	0.03458 (18)	0.2127 (4)	0.56166 (10)	0.0674 (5)
H14A	0.0089	0.2980	0.5246	0.101*	0.80 (2)
H14B	−0.0387	0.1481	0.5772	0.101*	0.80 (2)
H14C	0.0894	0.0592	0.5571	0.101*	0.80 (2)
H14D	0.0782	0.1894	0.5287	0.101*	0.20 (2)
H14E	−0.0498	0.2772	0.5490	0.101*	0.20 (2)
H14F	0.0312	0.0386	0.5813	0.101*	0.20 (2)

	U11	U22	U33	U12	U13	U23
Cl1	0.1230 (6)	0.1310 (7)	0.0666 (4)	0.0156 (4)	0.0405 (4)	−0.0055 (3)
O1	0.0955 (10)	0.0364 (6)	0.0858 (10)	−0.0028 (6)	0.0300 (8)	−0.0084 (6)
N1	0.0646 (9)	0.0387 (7)	0.0550 (9)	0.0004 (7)	0.0135 (7)	−0.0055 (6)
C1	0.0528 (9)	0.0422 (8)	0.0589 (10)	0.0044 (7)	0.0127 (8)	0.0008 (7)
C2	0.0615 (11)	0.0564 (11)	0.0825 (14)	−0.0036 (9)	0.0262 (10)	−0.0072 (10)
C3	0.0733 (13)	0.0705 (13)	0.0893 (16)	0.0016 (11)	0.0393 (12)	0.0029 (12)
C4	0.0751 (12)	0.0740 (13)	0.0573 (11)	0.0188 (11)	0.0219 (10)	0.0049 (10)
C5	0.0737 (12)	0.0730 (13)	0.0589 (12)	−0.0012 (11)	0.0084 (10)	−0.0065 (10)
C6	0.0647 (11)	0.0613 (11)	0.0558 (11)	−0.0047 (9)	0.0148 (8)	−0.0007 (8)
C7	0.0511 (9)	0.0370 (8)	0.0618 (11)	0.0035 (7)	0.0114 (8)	−0.0008 (7)
C8	0.0647 (10)	0.0437 (9)	0.0469 (9)	0.0117 (8)	0.0061 (8)	−0.0010 (7)
C9	0.0674 (11)	0.0560 (10)	0.0516 (10)	0.0160 (9)	0.0131 (8)	0.0093 (8)
C10	0.0907 (15)	0.0869 (15)	0.0601 (13)	0.0279 (12)	0.0244 (11)	0.0179 (11)
C11	0.130 (2)	0.1023 (19)	0.0465 (12)	0.0468 (17)	0.0173 (14)	−0.0015 (12)
C12	0.127 (2)	0.0812 (15)	0.0567 (13)	0.0293 (16)	−0.0111 (14)	−0.0197 (11)
C13	0.0832 (14)	0.0610 (11)	0.0621 (13)	0.0098 (11)	−0.0027 (10)	−0.0134 (9)
C14	0.0638 (11)	0.0617 (11)	0.0782 (14)	−0.0026 (9)	0.0154 (10)	0.0057 (10)

Cl1—C4	1.742 (2)	C8—C9	1.396 (3)
O1—C7	1.2299 (19)	C9—C10	1.390 (3)
N1—C7	1.346 (2)	C9—C14	1.498 (3)
N1—C8	1.426 (2)	C10—C11	1.366 (3)
N1—H1	0.86 (2)	C10—H10	0.9400
C1—C2	1.382 (3)	C11—C12	1.363 (4)
C1—C6	1.389 (2)	C11—H11	0.9400
C1—C7	1.493 (2)	C12—C13	1.387 (3)
C2—C3	1.381 (3)	C12—H12	0.9400
C2—H2	0.9400	C13—H13	0.9400
C3—C4	1.376 (3)	C14—H14A	0.9700
C3—H3	0.9400	C14—H14B	0.9700
C4—C5	1.374 (3)	C14—H14C	0.9700
C5—C6	1.384 (3)	C14—H14D	0.9699
C5—H5	0.9400	C14—H14E	0.9700
C6—H6	0.9400	C14—H14F	0.9701
C8—C13	1.388 (3)
C7—N1—C8	125.15 (15)	C9—C10—H10	118.8
C7—N1—H1	116.5 (14)	C12—C11—C10	119.6 (2)
C8—N1—H1	118.3 (14)	C12—C11—H11	120.2
C2—C1—C6	118.81 (18)	C10—C11—H11	120.2
C2—C1—C7	118.80 (16)	C11—C12—C13	120.5 (2)
C6—C1—C7	122.26 (16)	C11—C12—H12	119.7
C3—C2—C1	121.15 (19)	C13—C12—H12	119.7
C3—C2—H2	119.4	C12—C13—C8	119.7 (2)
C1—C2—H2	119.4	C12—C13—H13	120.2
C4—C3—C2	118.77 (19)	C8—C13—H13	120.2
C4—C3—H3	120.6	C9—C14—H14A	109.5
C2—C3—H3	120.6	C9—C14—H14B	109.5
C5—C4—C3	121.57 (19)	H14A—C14—H14B	109.5
C5—C4—Cl1	118.99 (17)	C9—C14—H14C	109.5
C3—C4—Cl1	119.43 (17)	H14A—C14—H14C	109.5
C4—C5—C6	119.0 (2)	H14B—C14—H14C	109.5
C4—C5—H5	120.5	C9—C14—H14D	109.5
C6—C5—H5	120.5	H14A—C14—H14D	56.0
C5—C6—C1	120.66 (19)	H14B—C14—H14D	141.0
C5—C6—H6	119.7	H14C—C14—H14D	56.5
C1—C6—H6	119.7	C9—C14—H14E	109.5
O1—C7—N1	122.69 (17)	H14A—C14—H14E	56.5
O1—C7—C1	120.33 (15)	H14B—C14—H14E	56.0
N1—C7—C1	116.95 (14)	H14C—C14—H14E	141.1
C13—C8—C9	120.40 (18)	H14D—C14—H14E	109.5
C13—C8—N1	120.71 (18)	C9—C14—H14F	109.5
C9—C8—N1	118.89 (15)	H14A—C14—H14F	141.1
C10—C9—C8	117.52 (19)	H14B—C14—H14F	56.5
C10—C9—C14	120.6 (2)	H14C—C14—H14F	56.0
C8—C9—C14	121.86 (17)	H14D—C14—H14F	109.5
C11—C10—C9	122.3 (2)	H14E—C14—H14F	109.5
C11—C10—H10	118.8
C6—C1—C2—C3	−0.9 (3)	C6—C1—C7—N1	34.7 (2)
C7—C1—C2—C3	−176.85 (16)	C7—N1—C8—C13	−42.7 (2)
C1—C2—C3—C4	1.4 (3)	C7—N1—C8—C9	136.99 (18)
C2—C3—C4—C5	−0.8 (3)	C13—C8—C9—C10	1.4 (3)
C2—C3—C4—Cl1	−179.63 (15)	N1—C8—C9—C10	−178.29 (15)
C3—C4—C5—C6	−0.1 (3)	C13—C8—C9—C14	−179.35 (17)
Cl1—C4—C5—C6	178.64 (14)	N1—C8—C9—C14	1.0 (2)
C4—C5—C6—C1	0.6 (3)	C8—C9—C10—C11	0.5 (3)
C2—C1—C6—C5	−0.1 (3)	C14—C9—C10—C11	−178.77 (18)
C7—C1—C6—C5	175.69 (16)	C9—C10—C11—C12	−1.5 (3)
C8—N1—C7—O1	5.6 (3)	C10—C11—C12—C13	0.6 (4)
C8—N1—C7—C1	−172.29 (15)	C11—C12—C13—C8	1.3 (3)
C2—C1—C7—O1	32.5 (2)	C9—C8—C13—C12	−2.3 (3)
C6—C1—C7—O1	−143.28 (18)	N1—C8—C13—C12	177.40 (16)
C2—C1—C7—N1	−149.49 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86 (2)	2.07 (2)	2.9073 (18)	164.1 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86 (2)	2.07 (2)	2.9073 (18)	164.1 (17)

Symmetry code: (i) .