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

In the title compound, C(15)H(14)ClNO, the ortho- and meta-methyl substituents in the aniline ring are anti to the N-H bond. The dihedral angle between the benzoyl and aniline benzene rings is 95.0 (1)°. N-H⋯O hydrogen bonds and C-H⋯π inter-actions link the mol-ecules in the crystal structure.

Related literature

For the preparation of the title compound, see: Gowda et al. (1996 ▶, 2001 ▶). 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. (2001 ▶); Rodrigues et al. (2011 ▶), on N-(ar­yl)-methane­sulfonamides, see: Jayalakshmi & Gowda (2004 ▶), on N-(ar­yl)-aryl­sulfonamides, see: Gowda et al. (2005 ▶) and on N-chloro­aryl­amides, see: Gowda et al. (1996 ▶).

Experimental

Crystal data

C15H14ClNO

M = 259.72

Monoclinic,

a = 8.1082 (8) Å

b = 19.5189 (17) Å

c = 9.2943 (9) Å

β = 111.957 (11)°

V = 1364.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 293 K

0.90 × 0.15 × 0.09 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009 ▶), based on expressions derived by Clark & Reid (1995 ▶)] T min = 0.953, T max = 0.976

22574 measured reflections

2793 independent reflections

1923 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.145

S = 1.04

2793 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.30 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/S1600536811053256/bq2325sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811053256/bq2325Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811053256/bq2325Isup3.cml

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

C15H14ClNO	F(000) = 544
Mr = 259.72	Dx = 1.265 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3994 reflections
a = 8.1082 (8) Å	θ = 3.4–26.4°
b = 19.5189 (17) Å	µ = 0.27 mm−1
c = 9.2943 (9) Å	T = 293 K
β = 111.957 (11)°	Rod, colorless
V = 1364.3 (2) Å3	0.90 × 0.15 × 0.09 mm
Z = 4

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2793 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1923 reflections with I > 2σ(I)
graphite	Rint = 0.058
Detector resolution: 10.4340 pixels mm-1	θmax = 26.4°, θmin = 3.4°
ω scans	h = −10→10
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]	k = −24→24
Tmin = 0.953, Tmax = 0.976	l = −11→11
22574 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0671P)2 + 0.3246P] where P = (Fo2 + 2Fc2)/3
2793 reflections	(Δ/σ)max < 0.001
165 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.30 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	0.7781 (3)	0.70473 (10)	0.5747 (2)	0.0420 (5)
C2	0.6708 (3)	0.65266 (10)	0.6192 (2)	0.0412 (5)
C3	0.5249 (3)	0.62384 (11)	0.5034 (2)	0.0512 (6)
H3	0.4980	0.6366	0.4007	0.061*
C4	0.4194 (3)	0.57674 (12)	0.5382 (3)	0.0569 (6)
H4	0.3211	0.5579	0.4600	0.068*
C5	0.4614 (3)	0.55780 (11)	0.6907 (3)	0.0520 (6)
C6	0.6067 (3)	0.58405 (11)	0.8067 (3)	0.0527 (6)
H6	0.6348	0.5700	0.9087	0.063*
C7	0.7116 (3)	0.63166 (11)	0.7710 (2)	0.0477 (5)
H7	0.8106	0.6498	0.8496	0.057*
C8	0.9834 (3)	0.80088 (10)	0.6627 (2)	0.0409 (5)
C9	1.1274 (3)	0.78514 (11)	0.6215 (2)	0.0442 (5)
C10	1.2233 (3)	0.83941 (13)	0.5917 (3)	0.0555 (6)
C11	1.1751 (3)	0.90633 (14)	0.6085 (3)	0.0653 (7)
H11	1.2375	0.9423	0.5867	0.078*
C12	1.0378 (3)	0.92083 (12)	0.6563 (3)	0.0605 (6)
H12	1.0103	0.9660	0.6697	0.073*
C13	0.9411 (3)	0.86789 (11)	0.6842 (2)	0.0488 (5)
H13	0.8483	0.8771	0.7171	0.059*
C14	1.1822 (3)	0.71233 (12)	0.6117 (3)	0.0608 (6)
H14A	1.3083	0.7079	0.6662	0.073*
H14B	1.1521	0.7000	0.5049	0.073*
H14C	1.1214	0.6825	0.6576	0.073*
C15	1.3817 (4)	0.82577 (19)	0.5477 (3)	0.0854 (9)
H15A	1.4244	0.8683	0.5228	0.103*
H15B	1.3471	0.7959	0.4592	0.103*
H15C	1.4742	0.8045	0.6332	0.103*
N1	0.8765 (2)	0.74774 (8)	0.68807 (18)	0.0440 (4)
H1	0.8747	0.7429	0.7794	0.053*
O1	0.7749 (2)	0.70745 (8)	0.44138 (16)	0.0549 (4)
Cl1	0.32708 (12)	0.49969 (4)	0.73735 (11)	0.0947 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0504 (12)	0.0442 (11)	0.0388 (11)	0.0029 (9)	0.0251 (10)	0.0015 (8)
C2	0.0484 (12)	0.0416 (11)	0.0401 (11)	0.0007 (9)	0.0240 (9)	−0.0021 (8)
C3	0.0616 (14)	0.0523 (13)	0.0416 (12)	−0.0033 (11)	0.0214 (11)	−0.0019 (9)
C4	0.0549 (14)	0.0555 (14)	0.0572 (14)	−0.0105 (11)	0.0172 (11)	−0.0070 (11)
C5	0.0592 (14)	0.0420 (12)	0.0643 (14)	−0.0042 (10)	0.0338 (12)	0.0003 (10)
C6	0.0682 (15)	0.0497 (13)	0.0467 (12)	0.0001 (11)	0.0287 (12)	0.0061 (10)
C7	0.0559 (13)	0.0501 (13)	0.0402 (11)	−0.0053 (10)	0.0216 (10)	0.0008 (9)
C8	0.0455 (11)	0.0463 (11)	0.0326 (10)	0.0001 (9)	0.0166 (9)	0.0014 (8)
C9	0.0438 (11)	0.0568 (13)	0.0330 (10)	0.0028 (9)	0.0154 (9)	0.0018 (9)
C10	0.0445 (12)	0.0769 (17)	0.0438 (12)	−0.0080 (11)	0.0150 (10)	0.0031 (11)
C11	0.0634 (16)	0.0702 (17)	0.0576 (14)	−0.0220 (13)	0.0174 (13)	0.0082 (12)
C12	0.0665 (16)	0.0459 (13)	0.0603 (15)	−0.0044 (11)	0.0137 (13)	−0.0010 (10)
C13	0.0507 (12)	0.0474 (12)	0.0482 (12)	0.0028 (10)	0.0184 (10)	−0.0032 (9)
C14	0.0598 (14)	0.0712 (16)	0.0548 (14)	0.0188 (12)	0.0254 (12)	−0.0006 (11)
C15	0.0616 (17)	0.130 (3)	0.0768 (19)	−0.0217 (17)	0.0397 (15)	−0.0039 (17)
N1	0.0571 (11)	0.0474 (10)	0.0365 (9)	−0.0051 (8)	0.0279 (8)	−0.0030 (7)
O1	0.0729 (11)	0.0630 (10)	0.0374 (8)	−0.0119 (8)	0.0306 (8)	−0.0022 (6)
Cl1	0.1000 (6)	0.0811 (5)	0.1190 (7)	−0.0323 (4)	0.0592 (5)	0.0043 (4)

C1—O1	1.231 (2)	C9—C10	1.401 (3)
C1—N1	1.350 (3)	C9—C14	1.502 (3)
C1—C2	1.493 (3)	C10—C11	1.389 (4)
C2—C7	1.385 (3)	C10—C15	1.510 (3)
C2—C3	1.386 (3)	C11—C12	1.374 (3)
C3—C4	1.374 (3)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.379 (3)
C4—C5	1.378 (3)	C12—H12	0.9300
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.365 (3)	C14—H14A	0.9600
C5—Cl1	1.736 (2)	C14—H14B	0.9600
C6—C7	1.381 (3)	C14—H14C	0.9600
C6—H6	0.9300	C15—H15A	0.9600
C7—H7	0.9300	C15—H15B	0.9600
C8—C13	1.386 (3)	C15—H15C	0.9600
C8—C9	1.393 (3)	N1—H1	0.8600
C8—N1	1.427 (2)
O1—C1—N1	122.86 (18)	C11—C10—C9	119.2 (2)
O1—C1—C2	120.85 (18)	C11—C10—C15	120.0 (2)
N1—C1—C2	116.28 (16)	C9—C10—C15	120.7 (2)
C7—C2—C3	118.69 (19)	C12—C11—C10	121.7 (2)
C7—C2—C1	122.75 (18)	C12—C11—H11	119.1
C3—C2—C1	118.55 (17)	C10—C11—H11	119.1
C4—C3—C2	121.0 (2)	C11—C12—C13	119.5 (2)
C4—C3—H3	119.5	C11—C12—H12	120.2
C2—C3—H3	119.5	C13—C12—H12	120.2
C3—C4—C5	119.0 (2)	C12—C13—C8	119.4 (2)
C3—C4—H4	120.5	C12—C13—H13	120.3
C5—C4—H4	120.5	C8—C13—H13	120.3
C6—C5—C4	121.3 (2)	C9—C14—H14A	109.5
C6—C5—Cl1	118.99 (17)	C9—C14—H14B	109.5
C4—C5—Cl1	119.68 (18)	H14A—C14—H14B	109.5
C5—C6—C7	119.3 (2)	C9—C14—H14C	109.5
C5—C6—H6	120.3	H14A—C14—H14C	109.5
C7—C6—H6	120.3	H14B—C14—H14C	109.5
C6—C7—C2	120.6 (2)	C10—C15—H15A	109.5
C6—C7—H7	119.7	C10—C15—H15B	109.5
C2—C7—H7	119.7	H15A—C15—H15B	109.5
C13—C8—C9	121.75 (19)	C10—C15—H15C	109.5
C13—C8—N1	117.64 (18)	H15A—C15—H15C	109.5
C9—C8—N1	120.59 (18)	H15B—C15—H15C	109.5
C8—C9—C10	118.2 (2)	C1—N1—C8	122.76 (15)
C8—C9—C14	121.53 (19)	C1—N1—H1	118.6
C10—C9—C14	120.3 (2)	C8—N1—H1	118.6
O1—C1—C2—C7	157.6 (2)	C13—C8—C9—C14	174.67 (19)
N1—C1—C2—C7	−22.5 (3)	N1—C8—C9—C14	−3.7 (3)
O1—C1—C2—C3	−21.9 (3)	C8—C9—C10—C11	1.9 (3)
N1—C1—C2—C3	157.99 (19)	C14—C9—C10—C11	−177.1 (2)
C7—C2—C3—C4	1.8 (3)	C8—C9—C10—C15	179.5 (2)
C1—C2—C3—C4	−178.6 (2)	C14—C9—C10—C15	0.6 (3)
C2—C3—C4—C5	−0.6 (3)	C9—C10—C11—C12	1.2 (3)
C3—C4—C5—C6	−1.1 (4)	C15—C10—C11—C12	−176.5 (2)
C3—C4—C5—Cl1	178.69 (18)	C10—C11—C12—C13	−2.0 (3)
C4—C5—C6—C7	1.4 (3)	C11—C12—C13—C8	−0.4 (3)
Cl1—C5—C6—C7	−178.32 (17)	C9—C8—C13—C12	3.5 (3)
C5—C6—C7—C2	−0.2 (3)	N1—C8—C13—C12	−178.07 (18)
C3—C2—C7—C6	−1.4 (3)	O1—C1—N1—C8	1.0 (3)
C1—C2—C7—C6	179.04 (19)	C2—C1—N1—C8	−178.89 (17)
C13—C8—C9—C10	−4.2 (3)	C13—C8—N1—C1	117.4 (2)
N1—C8—C9—C10	177.40 (17)	C9—C8—N1—C1	−64.2 (3)

Cg1 and Cg2 are the centroids of C2–C7 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.18	2.904 (2)	141.
C14—H14A···Cg1ii	0.96	2.94	3.653 (2)	132.
C7—H7···Cg2i	0.93	2.76	3.612 (2)	154.

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of C2–C7 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.18	2.904 (2)	141
C14—H14A⋯Cg1ii	0.96	2.94	3.653 (2)	132
C7—H7⋯Cg2i	0.93	2.76	3.612 (2)	154

Symmetry codes: (i) ; (ii) .