N-(2-Chloro-phen-yl)-3-methyl-benzamide.

In the title compound, C(14)H(12)ClNO, the N-H bond is anti to the carbonyl bond and the two aromatic rings make a dihedral angle of 5.4 (2)°. In the crystal, inter-molecular N-H⋯O hydrogen bonds connect the mol-ecules into chains running along the b axis. The chains are inter-connected through short Cl⋯Cl contacts [3.279 (1) Å].

Related literature

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

Experimental

Crystal data

C14H12ClNO

M = 245.7

Monoclinic,

a = 9.9972 (3) Å

b = 4.9124 (1) Å

c = 24.6662 (7) Å

β = 100.248 (3)°

V = 1192.04 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 295 K

0.55 × 0.35 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Ruby Gemini detector

Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.897, T max = 0.978

25420 measured reflections

2119 independent reflections

1884 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.108

S = 1.05

2119 reflections

157 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 global. DOI: 10.1107/S160053681000992X/bt5219sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681000992X/bt5219Isup2.hkl

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

C14H12ClNO	F(000) = 512
Mr = 245.7	Dx = 1.369 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 16100 reflections
a = 9.9972 (3) Å	θ = 2.1–29.5°
b = 4.9124 (1) Å	µ = 0.30 mm−1
c = 24.6662 (7) Å	T = 295 K
β = 100.248 (3)°	Block, colourless
V = 1192.04 (5) Å3	0.55 × 0.35 × 0.08 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Ruby Gemini detector	2119 independent reflections
graphite	1884 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1	Rint = 0.050
ω scans	θmax = 25.1°, θmin = 2.1°
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	h = −11→11
Tmin = 0.897, Tmax = 0.978	k = −5→5
25420 measured reflections	l = −29→29

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0534P)2 + 0.5999P] where P = (Fo2 + 2Fc2)/3
2119 reflections	(Δ/σ)max < 0.001
157 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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)
C1	0.29838 (18)	−0.1699 (3)	0.57259 (7)	0.0361 (4)
C2	0.28794 (18)	−0.0729 (3)	0.62913 (7)	0.0351 (4)
C3	0.19358 (19)	0.1212 (4)	0.63886 (8)	0.0379 (4)
H3	0.1363	0.1997	0.6091	0.045*
C4	0.18309 (19)	0.2001 (4)	0.69191 (8)	0.0396 (4)
C5	0.2713 (2)	0.0838 (4)	0.73564 (8)	0.0459 (5)
H5	0.2666	0.1359	0.7715	0.055*
C6	0.3659 (2)	−0.1087 (4)	0.72660 (8)	0.0479 (5)
H6	0.4246	−0.1841	0.7563	0.057*
C7	0.3737 (2)	−0.1891 (4)	0.67377 (8)	0.0425 (5)
H7	0.4362	−0.3211	0.6679	0.051*
C8	0.27931 (18)	−0.0271 (3)	0.47628 (7)	0.0349 (4)
C9	0.18735 (19)	0.1059 (4)	0.43608 (8)	0.0385 (4)
C10	0.1894 (2)	0.0693 (5)	0.38088 (8)	0.0523 (5)
H10	0.1269	0.1598	0.3546	0.063*
C11	0.2843 (3)	−0.1017 (5)	0.36470 (9)	0.0583 (6)
H11	0.2861	−0.1271	0.3275	0.07*
C12	0.3762 (2)	−0.2344 (5)	0.40389 (9)	0.0539 (5)
H12	0.4401	−0.3504	0.393	0.065*
C13	0.3748 (2)	−0.1975 (4)	0.45914 (8)	0.0437 (5)
H13	0.4382	−0.2873	0.4852	0.052*
C14	0.0792 (2)	0.4081 (4)	0.70160 (9)	0.0534 (5)
H14A	0.0666	0.3986	0.7392	0.08*	0.66 (3)
H14B	−0.0056	0.3716	0.6776	0.08*	0.66 (3)
H14C	0.1103	0.5868	0.6941	0.08*	0.66 (3)
H14D	0.0476	0.506	0.6681	0.08*	0.34 (3)
H14E	0.1198	0.5331	0.7297	0.08*	0.34 (3)
H14F	0.0039	0.3179	0.7132	0.08*	0.34 (3)
N1	0.27660 (16)	0.0202 (3)	0.53244 (6)	0.0373 (4)
H1N	0.2597	0.1834	0.5419	0.045*
O1	0.32539 (16)	−0.4076 (3)	0.56431 (6)	0.0511 (4)
Cl1	0.06537 (6)	0.31991 (12)	0.45519 (2)	0.0569 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0421 (10)	0.0259 (9)	0.0396 (10)	0.0012 (7)	0.0058 (8)	0.0004 (7)
C2	0.0404 (10)	0.0263 (9)	0.0390 (10)	−0.0015 (7)	0.0081 (8)	0.0021 (7)
C3	0.0458 (10)	0.0287 (9)	0.0389 (10)	0.0016 (8)	0.0067 (8)	0.0041 (7)
C4	0.0465 (11)	0.0300 (9)	0.0447 (10)	−0.0042 (8)	0.0149 (8)	−0.0015 (8)
C5	0.0594 (13)	0.0444 (11)	0.0355 (10)	−0.0052 (9)	0.0129 (9)	−0.0041 (8)
C6	0.0527 (12)	0.0505 (12)	0.0384 (10)	0.0024 (10)	0.0025 (9)	0.0049 (9)
C7	0.0457 (11)	0.0378 (10)	0.0441 (11)	0.0067 (8)	0.0079 (8)	0.0029 (8)
C8	0.0412 (10)	0.0264 (9)	0.0381 (9)	−0.0006 (7)	0.0096 (7)	−0.0024 (7)
C9	0.0423 (10)	0.0330 (9)	0.0410 (10)	0.0054 (8)	0.0097 (8)	−0.0023 (8)
C10	0.0593 (13)	0.0581 (13)	0.0383 (10)	0.0138 (11)	0.0052 (9)	0.0003 (9)
C11	0.0753 (15)	0.0626 (14)	0.0405 (11)	0.0123 (12)	0.0195 (10)	−0.0065 (10)
C12	0.0595 (13)	0.0512 (12)	0.0556 (13)	0.0149 (10)	0.0227 (10)	−0.0088 (10)
C13	0.0469 (11)	0.0386 (10)	0.0464 (11)	0.0100 (9)	0.0099 (9)	−0.0013 (9)
C14	0.0628 (14)	0.0444 (11)	0.0571 (13)	0.0064 (10)	0.0222 (10)	−0.0039 (10)
N1	0.0514 (9)	0.0248 (7)	0.0361 (8)	0.0072 (7)	0.0091 (7)	−0.0016 (6)
O1	0.0801 (10)	0.0252 (7)	0.0494 (8)	0.0073 (6)	0.0152 (7)	−0.0007 (6)
Cl1	0.0570 (3)	0.0622 (4)	0.0510 (3)	0.0279 (3)	0.0085 (2)	−0.0044 (2)

C1—O1	1.224 (2)	C9—C10	1.377 (3)
C1—N1	1.350 (2)	C9—Cl1	1.7375 (18)
C1—C2	1.495 (3)	C10—C11	1.378 (3)
C2—C7	1.392 (3)	C10—H10	0.93
C2—C3	1.392 (3)	C11—C12	1.374 (3)
C3—C4	1.386 (3)	C11—H11	0.93
C3—H3	0.93	C12—C13	1.377 (3)
C4—C5	1.389 (3)	C12—H12	0.93
C4—C14	1.507 (3)	C13—H13	0.93
C5—C6	1.384 (3)	C14—H14A	0.96
C5—H5	0.93	C14—H14B	0.96
C6—C7	1.377 (3)	C14—H14C	0.96
C6—H6	0.93	C14—H14D	0.96
C7—H7	0.93	C14—H14E	0.96
C8—C9	1.390 (3)	C14—H14F	0.96
C8—C13	1.391 (3)	N1—H1N	0.86
C8—N1	1.410 (2)
O1—C1—N1	123.31 (17)	C8—C9—Cl1	119.86 (14)
O1—C1—C2	120.91 (16)	C9—C10—C11	119.87 (19)
N1—C1—C2	115.78 (15)	C9—C10—H10	120.1
C7—C2—C3	119.03 (17)	C11—C10—H10	120.1
C7—C2—C1	118.18 (16)	C12—C11—C10	119.63 (19)
C3—C2—C1	122.76 (16)	C12—C11—H11	120.2
C4—C3—C2	121.43 (17)	C10—C11—H11	120.2
C4—C3—H3	119.3	C11—C12—C13	120.66 (19)
C2—C3—H3	119.3	C11—C12—H12	119.7
C3—C4—C5	118.30 (17)	C13—C12—H12	119.7
C3—C4—C14	120.62 (18)	C12—C13—C8	120.58 (19)
C5—C4—C14	121.08 (18)	C12—C13—H13	119.7
C6—C5—C4	120.91 (18)	C8—C13—H13	119.7
C6—C5—H5	119.5	C4—C14—H14A	109.5
C4—C5—H5	119.5	C4—C14—H14B	109.5
C7—C6—C5	120.24 (18)	C4—C14—H14C	109.5
C7—C6—H6	119.9	C4—C14—H14D	109.5
C5—C6—H6	119.9	C4—C14—H14E	109.5
C6—C7—C2	120.07 (18)	H14D—C14—H14E	109.5
C6—C7—H7	120	C4—C14—H14F	109.5
C2—C7—H7	120	H14D—C14—H14F	109.5
C9—C8—C13	117.94 (17)	H14E—C14—H14F	109.5
C9—C8—N1	119.86 (16)	C1—N1—C8	125.30 (15)
C13—C8—N1	122.16 (17)	C1—N1—H1N	117.3
C10—C9—C8	121.32 (17)	C8—N1—H1N	117.3
C10—C9—Cl1	118.82 (15)
O1—C1—C2—C7	34.3 (3)	N1—C8—C9—C10	178.40 (18)
N1—C1—C2—C7	−145.58 (18)	C13—C8—C9—Cl1	179.69 (14)
O1—C1—C2—C3	−143.6 (2)	N1—C8—C9—Cl1	−2.4 (2)
N1—C1—C2—C3	36.5 (2)	C8—C9—C10—C11	−0.1 (3)
C7—C2—C3—C4	−0.2 (3)	Cl1—C9—C10—C11	−179.31 (18)
C1—C2—C3—C4	177.67 (17)	C9—C10—C11—C12	0.0 (4)
C2—C3—C4—C5	1.1 (3)	C10—C11—C12—C13	−0.2 (4)
C2—C3—C4—C14	−179.28 (17)	C11—C12—C13—C8	0.6 (3)
C3—C4—C5—C6	−0.9 (3)	C9—C8—C13—C12	−0.8 (3)
C14—C4—C5—C6	179.54 (19)	N1—C8—C13—C12	−178.60 (18)
C4—C5—C6—C7	−0.3 (3)	O1—C1—N1—C8	1.2 (3)
C5—C6—C7—C2	1.3 (3)	C2—C1—N1—C8	−178.98 (16)
C3—C2—C7—C6	−1.0 (3)	C9—C8—N1—C1	142.39 (19)
C1—C2—C7—C6	−178.99 (18)	C13—C8—N1—C1	−39.8 (3)
C13—C8—C9—C10	0.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.86	2.16	2.936 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.86	2.16	2.936 (2)	151

Symmetry code: (i) .