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

In the mol-ecular structure of the title compound, C(14)H(12)ClNO, the meta-Cl atom in the benzoyl ring is positioned anti to the C=O bond, while the ortho-methyl group in the aniline ring is positioned syn to the N-H bond. The two benzene rings are nearly coplanar [dihedral angle = 3.48 (5)°]. The crystal structure is stabilized by N-H⋯O hydrogen bonds, which link the mol-ecules into chains along the b axis.

Related literature

For the preparation of the title compound, see: Gowda et al. (2003 ▶). For our studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Bowes et al. (2003 ▶); Gowda et al. (2000 ▶); Rodrigues et al. (2011 ▶); Saeed et al. (2010 ▶), on N-(ar­yl)-methane­sulfonamides, see: Jayalakshmi & Gowda (2004 ▶) on N-(ar­yl)-aryl­sulfonamides, see: Shetty & Gowda (2005 ▶) and on N-chloro­aryl­amides, see: Gowda et al. (1996 ▶).

Experimental

Crystal data

C14H12ClNO

M = 245.70

Monoclinic,

a = 11.1699 (5) Å

b = 4.9171 (2) Å

c = 21.4778 (8) Å

β = 90.339 (3)°

V = 1179.63 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 293 K

0.83 × 0.55 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009 ▶), based on expressions derived from Clark & Reid (1995 ▶)] T min = 0.818, T max = 0.970

22104 measured reflections

2411 independent reflections

2154 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.098

S = 1.04

2411 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2002 ▶); software used to prepare material for publication: enCIFer (Allen et al., 2004 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811048756/bq2320sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048756/bq2320Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811048756/bq2320Isup3.cml

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

C14H12ClNO	F(000) = 512
Mr = 245.70	Dx = 1.383 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7179 reflections
a = 11.1699 (5) Å	θ = 3.4–26.4°
b = 4.9171 (2) Å	µ = 0.31 mm−1
c = 21.4778 (8) Å	T = 293 K
β = 90.339 (3)°	Rod, colorless
V = 1179.63 (8) Å3	0.83 × 0.55 × 0.10 mm
Z = 4

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2411 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2154 reflections with I > 2σ(I)
graphite	Rint = 0.050
Detector resolution: 10.4340 pixels mm-1	θmax = 26.4°, θmin = 3.4°
ω scans	h = −13→13
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived from Clark & Reid (1995)]	k = −6→6
Tmin = 0.818, Tmax = 0.970	l = −26→26
22104 measured reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0481P)2 + 0.4496P] where P = (Fo2 + 2Fc2)/3
2411 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived (Clark & Reid, 1995).

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	0.78713 (15)	0.6810 (3)	0.51026 (8)	0.0347 (4)
C2	0.84225 (16)	0.5801 (3)	0.45112 (8)	0.0342 (4)
C3	0.78692 (16)	0.3823 (3)	0.41438 (8)	0.0357 (4)
H3A	0.7150	0.3041	0.4267	0.043*
C4	0.84060 (17)	0.3043 (3)	0.35942 (8)	0.0380 (4)
C5	0.94821 (18)	0.4136 (4)	0.34075 (9)	0.0434 (4)
H5A	0.9839	0.3563	0.3040	0.052*
C6	1.00224 (17)	0.6092 (4)	0.37740 (9)	0.0452 (4)
H6A	1.0750	0.6837	0.3652	0.054*
C7	0.94945 (17)	0.6957 (4)	0.43205 (8)	0.0395 (4)
H7A	0.9856	0.8308	0.4559	0.047*
C8	0.66916 (16)	0.5439 (3)	0.60171 (8)	0.0333 (4)
C9	0.56240 (16)	0.4044 (3)	0.61282 (8)	0.0362 (4)
C10	0.50367 (19)	0.4563 (4)	0.66843 (9)	0.0483 (5)
H10A	0.4327	0.3650	0.6769	0.058*
C11	0.5475 (2)	0.6388 (5)	0.71132 (9)	0.0547 (5)
H11A	0.5059	0.6712	0.7479	0.066*
C12	0.6531 (2)	0.7737 (4)	0.69999 (9)	0.0513 (5)
H12A	0.6831	0.8967	0.7290	0.062*
C13	0.71473 (18)	0.7262 (4)	0.64539 (8)	0.0418 (4)
H13A	0.7865	0.8159	0.6379	0.050*
C14	0.51064 (18)	0.2054 (4)	0.56700 (9)	0.0446 (4)
H14C	0.4336	0.1460	0.5811	0.053*
H14B	0.5630	0.0515	0.5635	0.053*
H14A	0.5022	0.2914	0.5271	0.053*
N1	0.73102 (13)	0.4923 (3)	0.54513 (6)	0.0348 (3)
H1A	0.7328	0.3269	0.5321	0.042*
O1	0.79372 (14)	0.9221 (2)	0.52456 (7)	0.0504 (4)
Cl1	0.77036 (5)	0.06380 (10)	0.31224 (2)	0.05338 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0383 (9)	0.0273 (8)	0.0386 (9)	0.0012 (7)	0.0004 (7)	−0.0005 (7)
C2	0.0385 (9)	0.0286 (8)	0.0356 (8)	0.0035 (7)	0.0020 (7)	0.0037 (6)
C3	0.0392 (9)	0.0319 (8)	0.0361 (8)	−0.0009 (7)	0.0040 (7)	0.0026 (7)
C4	0.0462 (10)	0.0328 (9)	0.0348 (9)	0.0036 (7)	−0.0019 (7)	0.0011 (7)
C5	0.0481 (10)	0.0468 (11)	0.0353 (9)	0.0062 (8)	0.0088 (8)	0.0017 (8)
C6	0.0383 (10)	0.0503 (11)	0.0469 (10)	−0.0025 (8)	0.0074 (8)	0.0069 (9)
C7	0.0415 (9)	0.0370 (9)	0.0401 (9)	−0.0023 (7)	0.0002 (7)	0.0013 (7)
C8	0.0386 (9)	0.0278 (8)	0.0336 (8)	0.0039 (7)	0.0019 (7)	−0.0005 (6)
C9	0.0406 (9)	0.0313 (8)	0.0369 (9)	0.0024 (7)	0.0002 (7)	−0.0004 (7)
C10	0.0485 (11)	0.0481 (11)	0.0484 (11)	−0.0019 (9)	0.0127 (9)	−0.0004 (9)
C11	0.0669 (14)	0.0582 (12)	0.0393 (10)	0.0033 (11)	0.0142 (9)	−0.0078 (9)
C12	0.0666 (13)	0.0481 (11)	0.0392 (10)	0.0016 (10)	−0.0026 (9)	−0.0138 (8)
C13	0.0449 (10)	0.0374 (9)	0.0429 (10)	−0.0016 (8)	−0.0011 (8)	−0.0074 (8)
C14	0.0440 (10)	0.0418 (10)	0.0479 (10)	−0.0062 (8)	0.0002 (8)	−0.0041 (8)
N1	0.0439 (8)	0.0258 (6)	0.0348 (7)	0.0000 (6)	0.0058 (6)	−0.0047 (5)
O1	0.0717 (10)	0.0252 (6)	0.0547 (8)	−0.0019 (6)	0.0158 (7)	−0.0037 (5)
Cl1	0.0666 (3)	0.0502 (3)	0.0434 (3)	−0.0055 (2)	−0.0005 (2)	−0.0113 (2)

C1—O1	1.227 (2)	C8—C9	1.398 (3)
C1—N1	1.349 (2)	C8—N1	1.424 (2)
C1—C2	1.499 (2)	C9—C10	1.390 (3)
C2—C7	1.389 (3)	C9—C14	1.501 (2)
C2—C3	1.395 (2)	C10—C11	1.374 (3)
C3—C4	1.381 (2)	C10—H10A	0.9300
C3—H3A	0.9300	C11—C12	1.376 (3)
C4—C5	1.378 (3)	C11—H11A	0.9300
C4—Cl1	1.7412 (18)	C12—C13	1.383 (3)
C5—C6	1.380 (3)	C12—H12A	0.9300
C5—H5A	0.9300	C13—H13A	0.9300
C6—C7	1.384 (3)	C14—H14C	0.9600
C6—H6A	0.9300	C14—H14B	0.9600
C7—H7A	0.9300	C14—H14A	0.9600
C8—C13	1.392 (2)	N1—H1A	0.8600
O1—C1—N1	123.60 (16)	C10—C9—C8	117.66 (17)
O1—C1—C2	120.50 (16)	C10—C9—C14	120.08 (17)
N1—C1—C2	115.91 (14)	C8—C9—C14	122.26 (16)
C7—C2—C3	119.89 (16)	C11—C10—C9	121.86 (19)
C7—C2—C1	118.25 (16)	C11—C10—H10A	119.1
C3—C2—C1	121.82 (16)	C9—C10—H10A	119.1
C4—C3—C2	118.93 (17)	C10—C11—C12	119.91 (18)
C4—C3—H3A	120.5	C10—C11—H11A	120.0
C2—C3—H3A	120.5	C12—C11—H11A	120.0
C5—C4—C3	121.61 (17)	C11—C12—C13	119.99 (18)
C5—C4—Cl1	119.08 (14)	C11—C12—H12A	120.0
C3—C4—Cl1	119.31 (14)	C13—C12—H12A	120.0
C4—C5—C6	119.01 (17)	C12—C13—C8	119.91 (18)
C4—C5—H5A	120.5	C12—C13—H13A	120.0
C6—C5—H5A	120.5	C8—C13—H13A	120.0
C5—C6—C7	120.75 (18)	C9—C14—H14C	109.5
C5—C6—H6A	119.6	C9—C14—H14B	109.5
C7—C6—H6A	119.6	H14C—C14—H14B	109.5
C6—C7—C2	119.78 (17)	C9—C14—H14A	109.5
C6—C7—H7A	120.1	H14C—C14—H14A	109.5
C2—C7—H7A	120.1	H14B—C14—H14A	109.5
C13—C8—C9	120.67 (16)	C1—N1—C8	125.45 (14)
C13—C8—N1	120.84 (16)	C1—N1—H1A	117.3
C9—C8—N1	118.48 (15)	C8—N1—H1A	117.3
O1—C1—C2—C7	36.2 (2)	N1—C8—C9—C10	179.64 (16)
N1—C1—C2—C7	−144.13 (16)	C13—C8—C9—C14	−179.74 (17)
O1—C1—C2—C3	−141.61 (19)	N1—C8—C9—C14	−0.6 (3)
N1—C1—C2—C3	38.0 (2)	C8—C9—C10—C11	0.3 (3)
C7—C2—C3—C4	0.2 (3)	C14—C9—C10—C11	−179.4 (2)
C1—C2—C3—C4	177.98 (15)	C9—C10—C11—C12	−0.7 (3)
C2—C3—C4—C5	1.2 (3)	C10—C11—C12—C13	0.3 (3)
C2—C3—C4—Cl1	−178.37 (13)	C11—C12—C13—C8	0.6 (3)
C3—C4—C5—C6	−1.2 (3)	C9—C8—C13—C12	−1.0 (3)
Cl1—C4—C5—C6	178.37 (15)	N1—C8—C13—C12	179.91 (17)
C4—C5—C6—C7	−0.2 (3)	O1—C1—N1—C8	1.9 (3)
C5—C6—C7—C2	1.6 (3)	C2—C1—N1—C8	−177.71 (15)
C3—C2—C7—C6	−1.5 (3)	C13—C8—N1—C1	−40.0 (3)
C1—C2—C7—C6	−179.42 (16)	C9—C8—N1—C1	140.87 (17)
C13—C8—C9—C10	0.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.86	2.11	2.9237 (18)	158.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.86	2.11	2.9237 (18)	158

Symmetry code: (i) .