2-Chloro-N-(2,3-dimethyl-phen-yl)benzamide.

In the title compound, C(15)H(14)ClNO, the N-H and C=O bonds in the amide group are anti to each other. The amide group is inclined at 60.3 (1)° to the chloro-substituted benzoyl ring and at 59.2 (1)° to the dimethyl-substituted aniline ring. The mean planes through the two benzene rings make a dihedral angle of 7.7 (1)°. In the crystal structure, mol-ecules are linked by inter-molecular N-H⋯O hydrogen bonds, forming chains along [010].

Related literature

For the preparation of the title compound, see: Gowda, Jyothi et al. (2003 ▶). For related structures, see: Gowda, Foro et al. (2008 ▶, 2009 ▶); Gowda, Jyothi et al. (2003 ▶); Gowda, Tokarčík et al. (2009 ▶). For a review of halogen bonding, see: Fourmigué (2009 ▶).

Experimental

Crystal data

C15H14ClNO

M = 259.72

Monoclinic,

a = 13.0108 (5) Å

b = 4.9970 (1) Å

c = 22.6241 (9) Å

β = 118.553 (4)°

V = 1292.01 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 295 K

0.54 × 0.43 × 0.05 mm

Data collection

Oxford Diffraction Gemini R CCD diffractometer

Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.861, T max = 0.985

20701 measured reflections

2293 independent reflections

1959 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.102

S = 1.06

2293 reflections

166 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.20 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 I, global. DOI: 10.1107/S1600536810024943/tk2683sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024943/tk2683Isup2.hkl

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

C15H14ClNO	F(000) = 544
Mr = 259.72	Dx = 1.335 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 11536 reflections
a = 13.0108 (5) Å	θ = 2.0–29.4°
b = 4.9970 (1) Å	µ = 0.28 mm−1
c = 22.6241 (9) Å	T = 295 K
β = 118.553 (4)°	Plate, colorless
V = 1292.01 (9) Å3	0.54 × 0.43 × 0.05 mm
Z = 4

Oxford Diffraction Gemini R CCD diffractometer	2293 independent reflections
graphite	1959 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1	Rint = 0.027
ω scans	θmax = 25.1°, θmin = 2.1°
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	h = −15→15
Tmin = 0.861, Tmax = 0.985	k = −5→5
20701 measured reflections	l = −26→26

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0467P)2 + 0.5282P] where P = (Fo2 + 2Fc2)/3
2293 reflections	(Δ/σ)max < 0.001
166 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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	0.44821 (16)	0.5493 (3)	0.33073 (9)	0.0402 (4)
C2	0.32436 (15)	0.4698 (3)	0.28284 (9)	0.0377 (4)
C3	0.22925 (17)	0.5896 (4)	0.28448 (9)	0.0422 (4)
C4	0.11586 (17)	0.5209 (4)	0.23906 (10)	0.0525 (5)
H4	0.0534	0.6029	0.2411	0.063*
C5	0.09558 (18)	0.3309 (4)	0.19085 (11)	0.0552 (5)
H5	0.0192	0.2849	0.16	0.066*
C6	0.18775 (18)	0.2085 (4)	0.18810 (10)	0.0525 (5)
H6	0.1737	0.0797	0.1554	0.063*
C7	0.30116 (17)	0.2768 (4)	0.23385 (9)	0.0449 (4)
H7	0.3631	0.1922	0.2318	0.054*
C8	0.63848 (15)	0.3676 (3)	0.41456 (9)	0.0392 (4)
C9	0.68395 (16)	0.5350 (3)	0.47093 (9)	0.0411 (4)
C10	0.80539 (17)	0.5320 (4)	0.51345 (9)	0.0463 (5)
C11	0.87516 (17)	0.3630 (4)	0.49984 (10)	0.0523 (5)
H11	0.9555	0.3622	0.5285	0.063*
C12	0.82881 (18)	0.1955 (4)	0.44484 (11)	0.0538 (5)
H12	0.8772	0.081	0.4368	0.065*
C13	0.71009 (17)	0.1991 (4)	0.40184 (10)	0.0475 (5)
H13	0.678	0.0882	0.3642	0.057*
C14	0.6071 (2)	0.7104 (4)	0.48782 (11)	0.0550 (5)
H14A	0.6218	0.895	0.4827	0.083*
H14B	0.6242	0.6781	0.5335	0.083*
H14C	0.5264	0.6697	0.458	0.083*
C15	0.8603 (2)	0.7101 (5)	0.57434 (11)	0.0662 (6)
H15A	0.8367	0.8919	0.5611	0.099*
H15B	0.9439	0.6972	0.5947	0.099*
H15C	0.8353	0.6549	0.6061	0.099*
N1	0.51508 (13)	0.3484 (3)	0.36925 (8)	0.0424 (4)
H1N	0.4817	0.1971	0.3666	0.051*
O1	0.48384 (12)	0.7779 (3)	0.33335 (7)	0.0546 (4)
Cl1	0.25124 (5)	0.82447 (11)	0.34617 (3)	0.0650 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0486 (11)	0.0274 (9)	0.0474 (10)	−0.0033 (8)	0.0252 (9)	−0.0017 (8)
C2	0.0446 (10)	0.0279 (9)	0.0409 (9)	−0.0020 (7)	0.0206 (8)	0.0043 (7)
C3	0.0518 (11)	0.0332 (9)	0.0453 (10)	0.0006 (8)	0.0262 (9)	0.0016 (8)
C4	0.0452 (12)	0.0519 (12)	0.0599 (12)	0.0072 (9)	0.0249 (10)	0.0069 (10)
C5	0.0457 (11)	0.0538 (13)	0.0517 (12)	−0.0018 (9)	0.0117 (9)	0.0014 (10)
C6	0.0592 (13)	0.0467 (11)	0.0424 (10)	−0.0030 (10)	0.0167 (10)	−0.0061 (9)
C7	0.0496 (11)	0.0388 (10)	0.0474 (11)	0.0016 (8)	0.0241 (9)	−0.0004 (8)
C8	0.0423 (10)	0.0290 (9)	0.0431 (10)	−0.0061 (7)	0.0179 (8)	0.0023 (7)
C9	0.0521 (11)	0.0304 (9)	0.0419 (10)	−0.0070 (8)	0.0233 (9)	0.0028 (7)
C10	0.0532 (12)	0.0390 (10)	0.0389 (10)	−0.0133 (9)	0.0157 (9)	0.0054 (8)
C11	0.0420 (11)	0.0554 (12)	0.0517 (12)	−0.0055 (9)	0.0161 (9)	0.0097 (10)
C12	0.0505 (12)	0.0530 (12)	0.0619 (13)	0.0040 (10)	0.0301 (11)	0.0035 (10)
C13	0.0523 (12)	0.0400 (10)	0.0489 (11)	−0.0034 (9)	0.0232 (10)	−0.0050 (8)
C14	0.0676 (13)	0.0505 (12)	0.0531 (12)	−0.0021 (10)	0.0339 (11)	−0.0029 (10)
C15	0.0742 (16)	0.0584 (14)	0.0483 (12)	−0.0178 (12)	0.0150 (11)	−0.0045 (10)
N1	0.0448 (9)	0.0248 (7)	0.0513 (9)	−0.0071 (6)	0.0178 (7)	0.0000 (6)
O1	0.0565 (8)	0.0259 (7)	0.0734 (10)	−0.0080 (6)	0.0245 (7)	0.0035 (6)
Cl1	0.0793 (4)	0.0553 (4)	0.0724 (4)	−0.0015 (3)	0.0458 (3)	−0.0180 (3)

C1—O1	1.224 (2)	C9—C10	1.403 (3)
C1—N1	1.341 (2)	C9—C14	1.510 (3)
C1—C2	1.503 (3)	C10—C11	1.378 (3)
C2—C7	1.389 (3)	C10—C15	1.503 (3)
C2—C3	1.391 (3)	C11—C12	1.377 (3)
C3—C4	1.379 (3)	C11—H11	0.93
C3—Cl1	1.7395 (19)	C12—C13	1.377 (3)
C4—C5	1.373 (3)	C12—H12	0.93
C4—H4	0.93	C13—H13	0.93
C5—C6	1.374 (3)	C14—H14A	0.96
C5—H5	0.93	C14—H14B	0.96
C6—C7	1.380 (3)	C14—H14C	0.96
C6—H6	0.93	C15—H15A	0.96
C7—H7	0.93	C15—H15B	0.96
C8—C13	1.384 (3)	C15—H15C	0.96
C8—C9	1.398 (2)	N1—H1N	0.86
C8—N1	1.437 (2)
O1—C1—N1	123.65 (17)	C11—C10—C9	119.96 (18)
O1—C1—C2	122.16 (16)	C11—C10—C15	119.49 (19)
N1—C1—C2	114.18 (14)	C9—C10—C15	120.54 (19)
C7—C2—C3	117.59 (17)	C12—C11—C10	121.59 (19)
C7—C2—C1	120.52 (16)	C12—C11—H11	119.2
C3—C2—C1	121.87 (16)	C10—C11—H11	119.2
C4—C3—C2	121.45 (17)	C11—C12—C13	119.30 (19)
C4—C3—Cl1	118.23 (15)	C11—C12—H12	120.3
C2—C3—Cl1	120.29 (14)	C13—C12—H12	120.3
C5—C4—C3	119.67 (19)	C12—C13—C8	120.01 (18)
C5—C4—H4	120.2	C12—C13—H13	120
C3—C4—H4	120.2	C8—C13—H13	120
C4—C5—C6	120.22 (19)	C9—C14—H14A	109.5
C4—C5—H5	119.9	C9—C14—H14B	109.5
C6—C5—H5	119.9	H14A—C14—H14B	109.5
C5—C6—C7	119.95 (19)	C9—C14—H14C	109.5
C5—C6—H6	120	H14A—C14—H14C	109.5
C7—C6—H6	120	H14B—C14—H14C	109.5
C6—C7—C2	121.11 (18)	C10—C15—H15A	109.5
C6—C7—H7	119.4	C10—C15—H15B	109.5
C2—C7—H7	119.4	H15A—C15—H15B	109.5
C13—C8—C9	121.34 (17)	C10—C15—H15C	109.5
C13—C8—N1	116.40 (16)	H15A—C15—H15C	109.5
C9—C8—N1	122.15 (16)	H15B—C15—H15C	109.5
C8—C9—C10	117.77 (17)	C1—N1—C8	124.77 (14)
C8—C9—C14	122.37 (17)	C1—N1—H1N	117.6
C10—C9—C14	119.85 (17)	C8—N1—H1N	117.6
O1—C1—C2—C7	118.6 (2)	C13—C8—C9—C14	−176.88 (17)
N1—C1—C2—C7	−60.8 (2)	N1—C8—C9—C14	−0.9 (3)
O1—C1—C2—C3	−59.7 (3)	C8—C9—C10—C11	−1.6 (2)
N1—C1—C2—C3	120.86 (19)	C14—C9—C10—C11	177.02 (17)
C7—C2—C3—C4	−0.3 (3)	C8—C9—C10—C15	179.05 (17)
C1—C2—C3—C4	178.06 (17)	C14—C9—C10—C15	−2.4 (3)
C7—C2—C3—Cl1	177.75 (13)	C9—C10—C11—C12	0.3 (3)
C1—C2—C3—Cl1	−3.9 (2)	C15—C10—C11—C12	179.72 (19)
C2—C3—C4—C5	−0.2 (3)	C10—C11—C12—C13	0.9 (3)
Cl1—C3—C4—C5	−178.28 (16)	C11—C12—C13—C8	−0.8 (3)
C3—C4—C5—C6	0.4 (3)	C9—C8—C13—C12	−0.5 (3)
C4—C5—C6—C7	−0.1 (3)	N1—C8—C13—C12	−176.75 (17)
C5—C6—C7—C2	−0.4 (3)	O1—C1—N1—C8	−5.1 (3)
C3—C2—C7—C6	0.6 (3)	C2—C1—N1—C8	174.31 (16)
C1—C2—C7—C6	−177.78 (17)	C13—C8—N1—C1	−119.2 (2)
C13—C8—C9—C10	1.7 (3)	C9—C8—N1—C1	64.6 (2)
N1—C8—C9—C10	177.69 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.86	2.23	2.9388 (19)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.86	2.23	2.9388 (19)	140

Symmetry code: (i) .