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

In the title compound, C(15)H(14)ClNO, the N-H bond is trans to the C=O bond. The dihedral angle between the two aromatic rings is 5.5 (2)°. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into chains running along the a axis.

Related literature

For the preparation of the title compound, see: Gowda et al. (2003 ▶). For related structures, see: Bowes et al. (2003 ▶); Gowda et al. (2008 ▶, 2009 ▶).

Experimental

Crystal data

C15H14ClNO

M = 259.72

Orthorhombic,

a = 9.550 (1) Å

b = 10.104 (2) Å

c = 28.133 (4) Å

V = 2714.6 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.27 mm−1

T = 299 K

0.38 × 0.20 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.905, T max = 0.984

9354 measured reflections

2469 independent reflections

1405 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.086

wR(F 2) = 0.193

S = 1.16

2469 reflections

166 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810014972/bt5253sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014972/bt5253Isup2.hkl

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

C15H14ClNO	F(000) = 1088
Mr = 259.72	Dx = 1.271 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2409 reflections
a = 9.550 (1) Å	θ = 2.6–27.9°
b = 10.104 (2) Å	µ = 0.27 mm−1
c = 28.133 (4) Å	T = 299 K
V = 2714.6 (7) Å3	Needle, colourless
Z = 8	0.38 × 0.20 × 0.06 mm

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2469 independent reflections
Radiation source: fine-focus sealed tube	1405 reflections with I > 2σ(I)
graphite	Rint = 0.051
Rotation method data acquisition using ω and phi scans	θmax = 25.3°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −11→10
Tmin = 0.905, Tmax = 0.984	k = −7→12
9354 measured reflections	l = −24→33

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)] = 0.086	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.193	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	w = 1/[σ2(Fo2) + (0.0485P)2 + 3.5049P] where P = (Fo2 + 2Fc2)/3
2469 reflections	(Δ/σ)max = 0.003
166 parameters	Δρmax = 0.23 e Å−3
1 restraint	Δρmin = −0.23 e Å−3

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
C1	0.3133 (4)	0.2816 (4)	0.31176 (13)	0.0477 (10)
C2	0.2436 (5)	0.2315 (5)	0.35073 (13)	0.0576 (12)
H2	0.1655	0.1782	0.3459	0.069*
C3	0.2865 (5)	0.2583 (5)	0.39707 (13)	0.0581 (12)
C4	0.4057 (5)	0.3357 (5)	0.40367 (15)	0.0602 (13)
C5	0.4728 (5)	0.3856 (4)	0.36439 (16)	0.0611 (12)
H5	0.5514	0.4386	0.3689	0.073*
C6	0.4286 (5)	0.3605 (4)	0.31838 (14)	0.0551 (12)
H6	0.4759	0.3964	0.2925	0.066*
C7	0.3374 (4)	0.2232 (4)	0.22645 (13)	0.0500 (11)
C8	0.2595 (5)	0.1668 (4)	0.18478 (12)	0.0457 (10)
C9	0.3119 (5)	0.1932 (4)	0.13955 (13)	0.0564 (12)
H9	0.3899	0.2475	0.1363	0.068*
C10	0.2503 (6)	0.1405 (5)	0.09976 (14)	0.0663 (14)
H10	0.2859	0.1590	0.0697	0.080*
C11	0.1355 (6)	0.0602 (5)	0.10495 (15)	0.0655 (14)
C12	0.0799 (5)	0.0327 (4)	0.14903 (17)	0.0664 (13)
H12	0.0014	−0.0211	0.1520	0.080*
C13	0.1436 (5)	0.0869 (4)	0.18880 (15)	0.0573 (12)
H13	0.1072	0.0688	0.2188	0.069*
C14	0.2071 (6)	0.2009 (6)	0.43859 (15)	0.0912 (18)
H14A	0.2101	0.1061	0.4371	0.109*
H14B	0.1114	0.2300	0.4374	0.109*
H14C	0.2491	0.2302	0.4678	0.109*
C15	0.4610 (6)	0.3627 (5)	0.45336 (16)	0.0898 (18)
H15A	0.4821	0.2804	0.4688	0.108*
H15B	0.3915	0.4095	0.4714	0.108*
H15C	0.5445	0.4154	0.4513	0.108*
N1	0.2614 (3)	0.2460 (4)	0.26579 (11)	0.0547 (10)
H1N	0.1728 (14)	0.233 (4)	0.2629 (14)	0.066*
O1	0.4632 (3)	0.2440 (4)	0.22403 (10)	0.0739 (10)
Cl1	0.0598 (2)	−0.01106 (17)	0.05511 (5)	0.1200 (8)

	U11	U22	U33	U12	U13	U23
C1	0.038 (2)	0.061 (3)	0.044 (2)	−0.002 (2)	−0.0062 (18)	−0.007 (2)
C2	0.045 (3)	0.077 (3)	0.051 (2)	−0.007 (3)	0.001 (2)	−0.003 (2)
C3	0.066 (3)	0.070 (3)	0.038 (2)	0.007 (3)	0.002 (2)	−0.001 (2)
C4	0.072 (4)	0.059 (3)	0.050 (3)	0.007 (3)	−0.016 (2)	−0.010 (2)
C5	0.064 (3)	0.052 (3)	0.067 (3)	−0.012 (3)	−0.014 (3)	−0.009 (2)
C6	0.057 (3)	0.062 (3)	0.046 (2)	−0.009 (3)	−0.002 (2)	−0.002 (2)
C7	0.040 (3)	0.070 (3)	0.039 (2)	0.006 (2)	−0.0009 (19)	0.000 (2)
C8	0.042 (3)	0.056 (3)	0.039 (2)	0.008 (2)	−0.0043 (19)	−0.0027 (18)
C9	0.059 (3)	0.066 (3)	0.045 (2)	0.008 (3)	0.003 (2)	0.002 (2)
C10	0.089 (4)	0.076 (3)	0.034 (2)	0.018 (3)	−0.004 (2)	−0.005 (2)
C11	0.088 (4)	0.060 (3)	0.048 (3)	0.013 (3)	−0.020 (3)	−0.014 (2)
C12	0.072 (4)	0.054 (3)	0.074 (3)	−0.004 (3)	−0.013 (3)	−0.014 (2)
C13	0.063 (3)	0.060 (3)	0.050 (2)	0.002 (3)	0.005 (2)	−0.006 (2)
C14	0.096 (5)	0.125 (5)	0.052 (3)	−0.003 (4)	0.005 (3)	0.006 (3)
C15	0.128 (5)	0.084 (4)	0.058 (3)	0.001 (4)	−0.032 (3)	−0.014 (3)
N1	0.0341 (19)	0.087 (3)	0.0428 (18)	−0.007 (2)	−0.0019 (16)	−0.0121 (17)
O1	0.0312 (16)	0.138 (3)	0.0523 (18)	−0.003 (2)	0.0006 (13)	−0.0042 (18)
Cl1	0.1683 (18)	0.1139 (13)	0.0777 (10)	0.0066 (13)	−0.0518 (10)	−0.0319 (9)

C1—C6	1.372 (5)	C9—C10	1.372 (6)
C1—C2	1.379 (5)	C9—H9	0.9300
C1—N1	1.431 (5)	C10—C11	1.372 (7)
C2—C3	1.393 (5)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.378 (6)
C3—C4	1.394 (6)	C11—Cl1	1.734 (4)
C3—C14	1.508 (6)	C12—C13	1.386 (6)
C4—C5	1.374 (6)	C12—H12	0.9300
C4—C15	1.519 (6)	C13—H13	0.9300
C5—C6	1.385 (5)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—H6	0.9300	C14—H14C	0.9600
C7—O1	1.221 (5)	C15—H15A	0.9600
C7—N1	1.344 (5)	C15—H15B	0.9600
C7—C8	1.500 (5)	C15—H15C	0.9600
C8—C13	1.376 (6)	N1—H1N	0.860 (10)
C8—C9	1.393 (5)
C6—C1—C2	119.5 (4)	C9—C10—C11	119.0 (4)
C6—C1—N1	123.2 (4)	C9—C10—H10	120.5
C2—C1—N1	117.3 (4)	C11—C10—H10	120.5
C1—C2—C3	122.1 (4)	C10—C11—C12	121.6 (4)
C1—C2—H2	118.9	C10—C11—Cl1	119.5 (4)
C3—C2—H2	118.9	C12—C11—Cl1	118.9 (4)
C2—C3—C4	118.3 (4)	C11—C12—C13	118.5 (5)
C2—C3—C14	120.2 (4)	C11—C12—H12	120.7
C4—C3—C14	121.5 (4)	C13—C12—H12	120.7
C5—C4—C3	118.7 (4)	C8—C13—C12	121.3 (4)
C5—C4—C15	120.8 (5)	C8—C13—H13	119.4
C3—C4—C15	120.5 (5)	C12—C13—H13	119.4
C4—C5—C6	122.8 (4)	C3—C14—H14A	109.5
C4—C5—H5	118.6	C3—C14—H14B	109.5
C6—C5—H5	118.6	H14A—C14—H14B	109.5
C1—C6—C5	118.6 (4)	C3—C14—H14C	109.5
C1—C6—H6	120.7	H14A—C14—H14C	109.5
C5—C6—H6	120.7	H14B—C14—H14C	109.5
O1—C7—N1	123.2 (4)	C4—C15—H15A	109.5
O1—C7—C8	120.6 (4)	C4—C15—H15B	109.5
N1—C7—C8	116.2 (4)	H15A—C15—H15B	109.5
C13—C8—C9	118.5 (4)	C4—C15—H15C	109.5
C13—C8—C7	123.9 (4)	H15A—C15—H15C	109.5
C9—C8—C7	117.6 (4)	H15B—C15—H15C	109.5
C10—C9—C8	121.1 (5)	C7—N1—C1	126.9 (3)
C10—C9—H9	119.4	C7—N1—H1N	115 (3)
C8—C9—H9	119.4	C1—N1—H1N	118 (3)
C6—C1—C2—C3	−0.1 (7)	N1—C7—C8—C9	153.1 (4)
N1—C1—C2—C3	179.0 (4)	C13—C8—C9—C10	−0.3 (6)
C1—C2—C3—C4	−1.5 (7)	C7—C8—C9—C10	177.1 (4)
C1—C2—C3—C14	−179.8 (4)	C8—C9—C10—C11	−0.2 (7)
C2—C3—C4—C5	2.1 (6)	C9—C10—C11—C12	0.7 (7)
C14—C3—C4—C5	−179.6 (5)	C9—C10—C11—Cl1	−178.1 (3)
C2—C3—C4—C15	−177.2 (4)	C10—C11—C12—C13	−0.7 (7)
C14—C3—C4—C15	1.1 (7)	Cl1—C11—C12—C13	178.1 (3)
C3—C4—C5—C6	−1.1 (7)	C9—C8—C13—C12	0.3 (6)
C15—C4—C5—C6	178.1 (4)	C7—C8—C13—C12	−176.9 (4)
C2—C1—C6—C5	1.1 (6)	C11—C12—C13—C8	0.2 (7)
N1—C1—C6—C5	−178.0 (4)	O1—C7—N1—C1	−8.0 (8)
C4—C5—C6—C1	−0.5 (7)	C8—C7—N1—C1	170.8 (4)
O1—C7—C8—C13	149.2 (5)	C6—C1—N1—C7	34.7 (7)
N1—C7—C8—C13	−29.6 (6)	C2—C1—N1—C7	−144.4 (5)
O1—C7—C8—C9	−28.1 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.86 (1)	2.04 (2)	2.862 (5)	160 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.86 (1)	2.04 (2)	2.862 (5)	160 (4)

Symmetry code: (i) .