N-(2,6-Dichloro­phen­yl)-4-methyl­benzamide

Rodrigues, V.Z.; Foro, S.; Gowda, B.T.

doi:10.1107/S1600536811028935

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2123

doi:10.1107/S1600536811028935

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N-(2,6-Dichlorophenyl)-4-methylbenzamide

Vinola Z. Rodrigues,^a Sabine Foro ^b and B. Thimme Gowda ^a ^*

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287, Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 16 July 2011; accepted 18 July 2011; online 23 July 2011)

In the title compound, C₁₄H₁₁Cl₂NO, the two aromatic rings are nearly orthogonal to each other [dihedral angle 79.7 (1)°], while the central amide core –NH—C(=O)– is nearly coplanar with the benzoyl ring [N—C—C—C torsion angles = −5.5 (3) and 1772. (2)°]. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules into C(4) chains propagating in [001].

Related literature

For our studies on the effects of substituents on the structures of N-(aryl)-amides, see: Bhat & Gowda (2000 ); Gowda et al. (2006 , 2009 ), on N-(aryl)-methanesulfonamides, see: Jayalakshmi & Gowda (2004 ) and on N-(aryl)-arylsulfonamides, see: Gowda et al. (2005 ).

Experimental

Crystal data

C₁₄H₁₁Cl₂NO
M_r = 280.14
Tetragonal, I 4₁ /a
a = 16.4706 (8) Å
c = 19.8709 (9) Å
V = 5390.6 (4) Å³
Z = 16
Mo Kα radiation
μ = 0.47 mm⁻¹
T = 293 K
0.48 × 0.34 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.807, T_max = 0.937
5852 measured reflections
2752 independent reflections
1701 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.120
S = 1.01
2752 reflections
166 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.82 (2)	2.08 (2)	2.878 (2)	164 (2)
Symmetry code: (i) $[-y+{\script{3\over 4}}, x+{\script{1\over 4}}, z+{\script{1\over 4}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811028935/bt6816sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811028935/bt6816Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811028935/bt6816Isup3.cml

checkCIF report

Comment top

The amide moiety is an important constituent of many biologically significant compounds. As part of our studies on the effects of ring and side chain substitutions on the structures of N-(aryl)-amides (Bhat & Gowda, 2000; Gowda et al., 2006, 2009), N-(aryl)-methanesulfonamides (Jayalakshmi & Gowda, 2004) and N-(aryl)-arylsulfonamides (Gowda et al., 2005), the crystal structure of N-(2,6-dichlorophenyl)-4-methylbenzamide (I) has been determined (Fig. 1). The conformations of the N—H and C=O bonds in the amide segment of the structure are anti to each other, similar to that observed in N-(2,6-dimethylphenyl)-4-methylbenzamide (II) (Gowda et al., 2009) and other benzanilides, with similar bond parameters.

The two aromatic rings in the structure make the dihedral angle of 79.7 (1)°, compared to the value of 78.8 (1)° in (II). The central amide core –NH—C(=O)– is nearly coplanar with the benzoyl ring. The orientation of the anilino ring with respect to the amide core are given by the torsion angles, C2—C1—N1—C7 = 105.8 (3)° and C6—C1—N1—C7 = -74.5 (3)°.

Part of the crystal structure of (I), showing the formation of hydrogen- bonded layered chains (Table 1) running along b axis is shown in Fig.2.

Related literature top

For our studies on the effects of substituents on the structures of N-(aryl)-amides, see: Bhat & Gowda (2000); Gowda et al. (2006, 2009), on N-(aryl)-methanesulfonamides, see: Jayalakshmi & Gowda (2004) and on N-(aryl)-arylsulfonamides, see: Gowda et al. (2005).

Experimental top

The title compound was prepared by the method described by Gowda et al. (2009). The purity of the compound was checked and characterized by recording its infrared and NMR spectra.

Needle-like colourless single crystals of the title compound were obtained by slow evaporation from an ethanol solution of the compound (0.5 g in about 30 ml of ethanol) at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); 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: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of (I) showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.

N-(2,6-Dichlorophenyl)-4-methylbenzamide top

Crystal data top

C₁₄H₁₁Cl₂NO	D_x = 1.381 Mg m⁻³
M_r = 280.14	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4₁/a	Cell parameters from 1773 reflections
Hall symbol: -I 4ad	θ = 2.8–27.9°
a = 16.4706 (8) Å	µ = 0.47 mm⁻¹
c = 19.8709 (9) Å	T = 293 K
V = 5390.6 (4) Å³	Prism, colourless
Z = 16	0.48 × 0.34 × 0.14 mm
F(000) = 2304

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2752 independent reflections
Radiation source: fine-focus sealed tube	1701 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
Rotation method data acquisition using ω scans.	θ_max = 26.4°, θ_min = 3.0°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −12→17
T_min = 0.807, T_max = 0.937	k = −17→20
5852 measured reflections	l = −10→24

Refinement top

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0618P)² + 1.1095P] where P = (F_o² + 2F_c²)/3
2752 reflections	(Δ/σ)_max = 0.001
166 parameters	Δρ_max = 0.23 e Å⁻³
1 restraint	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₄H₁₁Cl₂NO	Z = 16
M_r = 280.14	Mo Kα radiation
Tetragonal, I4₁/a	µ = 0.47 mm⁻¹
a = 16.4706 (8) Å	T = 293 K
c = 19.8709 (9) Å	0.48 × 0.34 × 0.14 mm
V = 5390.6 (4) Å³

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2752 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	1701 reflections with I > 2σ(I)
T_min = 0.807, T_max = 0.937	R_int = 0.021
5852 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	1 restraint
wR(F²) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.23 e Å⁻³
2752 reflections	Δρ_min = −0.21 e Å⁻³
166 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.14058 (13)	0.52556 (15)	0.06376 (10)	0.0437 (5)
C2	0.07328 (15)	0.48135 (16)	0.08354 (12)	0.0542 (6)
C3	−0.00303 (16)	0.51539 (19)	0.08617 (14)	0.0686 (8)
H3	−0.0474	0.4849	0.1002	0.082*
C4	−0.01236 (17)	0.5952 (2)	0.06771 (14)	0.0707 (8)
H4	−0.0638	0.6186	0.0686	0.085*
C5	0.05259 (16)	0.64076 (17)	0.04806 (14)	0.0630 (7)
H5	0.0455	0.6947	0.0356	0.076*
C6	0.12874 (14)	0.60634 (16)	0.04678 (11)	0.0505 (6)
C7	0.25465 (13)	0.47064 (13)	0.00212 (10)	0.0397 (5)
C8	0.33829 (13)	0.43726 (13)	0.00489 (9)	0.0388 (5)
C9	0.37543 (16)	0.4135 (2)	−0.05361 (12)	0.0726 (9)
H9	0.3472	0.4172	−0.0940	0.087*
C10	0.45324 (17)	0.3845 (2)	−0.05353 (13)	0.0792 (9)
H10	0.4766	0.3692	−0.0942	0.095*
C11	0.49760 (14)	0.37724 (14)	0.00367 (12)	0.0497 (6)
C12	0.46104 (15)	0.40214 (18)	0.06207 (12)	0.0655 (8)
H12	0.4899	0.3992	0.1022	0.079*
C13	0.38295 (15)	0.43136 (17)	0.06293 (11)	0.0600 (7)
H13	0.3600	0.4474	0.1036	0.072*
C14	0.58324 (16)	0.34561 (19)	0.00401 (16)	0.0713 (8)
H14A	0.6167	0.3796	−0.0238	0.086*
H14B	0.5839	0.2912	−0.0132	0.086*
H14C	0.6038	0.3459	0.0492	0.086*
N1	0.21884 (11)	0.49001 (12)	0.06109 (8)	0.0462 (5)
H1N	0.2409 (14)	0.4795 (15)	0.0972 (9)	0.055*
O1	0.21852 (10)	0.48106 (11)	−0.05131 (7)	0.0548 (5)
Cl1	0.08438 (5)	0.37957 (5)	0.10321 (4)	0.0777 (3)
Cl2	0.21062 (4)	0.66582 (4)	0.02405 (4)	0.0717 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0379 (13)	0.0624 (16)	0.0309 (11)	0.0084 (11)	−0.0007 (9)	−0.0048 (10)
C2	0.0483 (15)	0.0640 (16)	0.0502 (14)	0.0043 (12)	−0.0027 (11)	0.0034 (11)
C3	0.0425 (15)	0.082 (2)	0.0817 (19)	0.0023 (14)	0.0067 (13)	0.0058 (15)
C4	0.0432 (16)	0.086 (2)	0.083 (2)	0.0163 (15)	0.0036 (14)	−0.0081 (16)
C5	0.0530 (16)	0.0590 (17)	0.0770 (18)	0.0150 (13)	−0.0009 (13)	−0.0057 (14)
C6	0.0438 (14)	0.0612 (16)	0.0465 (13)	0.0046 (11)	0.0013 (10)	−0.0056 (11)
C7	0.0430 (12)	0.0448 (13)	0.0315 (11)	0.0010 (10)	−0.0003 (9)	−0.0002 (9)
C8	0.0400 (12)	0.0426 (12)	0.0337 (11)	−0.0009 (10)	0.0014 (9)	−0.0010 (9)
C9	0.0600 (18)	0.120 (3)	0.0375 (13)	0.0260 (16)	−0.0047 (12)	−0.0161 (14)
C10	0.0616 (19)	0.127 (3)	0.0485 (15)	0.0296 (18)	0.0082 (14)	−0.0186 (16)
C11	0.0414 (13)	0.0509 (14)	0.0566 (14)	0.0011 (11)	0.0053 (11)	−0.0013 (11)
C12	0.0492 (16)	0.101 (2)	0.0461 (14)	0.0154 (14)	−0.0064 (12)	0.0001 (14)
C13	0.0492 (15)	0.095 (2)	0.0355 (13)	0.0157 (14)	0.0000 (11)	−0.0048 (12)
C14	0.0482 (16)	0.081 (2)	0.0845 (19)	0.0108 (14)	0.0077 (14)	−0.0042 (16)
N1	0.0414 (11)	0.0676 (14)	0.0297 (10)	0.0122 (9)	−0.0026 (8)	−0.0012 (9)
O1	0.0541 (10)	0.0812 (12)	0.0291 (8)	0.0129 (8)	−0.0065 (7)	−0.0015 (7)
Cl1	0.0697 (5)	0.0710 (5)	0.0924 (5)	0.0008 (4)	−0.0054 (4)	0.0200 (4)
Cl2	0.0594 (5)	0.0703 (5)	0.0853 (5)	−0.0040 (3)	0.0068 (3)	0.0012 (4)

Geometric parameters (Å, º) top

C1—C2	1.383 (3)	C8—C9	1.371 (3)
C1—C6	1.386 (3)	C8—C13	1.371 (3)
C1—N1	1.417 (3)	C9—C10	1.368 (4)
C2—C3	1.377 (3)	C9—H9	0.9300
C2—Cl1	1.731 (3)	C10—C11	1.357 (3)
C3—C4	1.374 (4)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.370 (3)
C4—C5	1.364 (4)	C11—C14	1.504 (3)
C4—H4	0.9300	C12—C13	1.373 (3)
C5—C6	1.377 (3)	C12—H12	0.9300
C5—H5	0.9300	C13—H13	0.9300
C6—Cl2	1.727 (2)	C14—H14A	0.9600
C7—O1	1.229 (2)	C14—H14B	0.9600
C7—N1	1.350 (3)	C14—H14C	0.9600
C7—C8	1.484 (3)	N1—H1N	0.823 (16)

C2—C1—C6	117.5 (2)	C10—C9—C8	121.1 (2)
C2—C1—N1	121.5 (2)	C10—C9—H9	119.4
C6—C1—N1	121.0 (2)	C8—C9—H9	119.4
C3—C2—C1	121.9 (3)	C11—C10—C9	122.4 (2)
C3—C2—Cl1	118.8 (2)	C11—C10—H10	118.8
C1—C2—Cl1	119.30 (19)	C9—C10—H10	118.8
C4—C3—C2	118.8 (3)	C10—C11—C12	116.5 (2)
C4—C3—H3	120.6	C10—C11—C14	122.7 (2)
C2—C3—H3	120.6	C12—C11—C14	120.8 (2)
C5—C4—C3	121.0 (3)	C11—C12—C13	121.8 (2)
C5—C4—H4	119.5	C11—C12—H12	119.1
C3—C4—H4	119.5	C13—C12—H12	119.1
C4—C5—C6	119.6 (3)	C8—C13—C12	121.1 (2)
C4—C5—H5	120.2	C8—C13—H13	119.4
C6—C5—H5	120.2	C12—C13—H13	119.4
C5—C6—C1	121.3 (2)	C11—C14—H14A	109.5
C5—C6—Cl2	118.9 (2)	C11—C14—H14B	109.5
C1—C6—Cl2	119.88 (17)	H14A—C14—H14B	109.5
O1—C7—N1	120.3 (2)	C11—C14—H14C	109.5
O1—C7—C8	122.21 (18)	H14A—C14—H14C	109.5
N1—C7—C8	117.44 (17)	H14B—C14—H14C	109.5
C9—C8—C13	117.0 (2)	C7—N1—C1	121.85 (17)
C9—C8—C7	119.24 (19)	C7—N1—H1N	120.9 (17)
C13—C8—C7	123.73 (19)	C1—N1—H1N	117.2 (17)

C6—C1—C2—C3	0.3 (4)	O1—C7—C8—C13	174.2 (2)
N1—C1—C2—C3	−179.9 (2)	N1—C7—C8—C13	−5.5 (3)
C6—C1—C2—Cl1	178.38 (16)	C13—C8—C9—C10	0.7 (4)
N1—C1—C2—Cl1	−1.8 (3)	C7—C8—C9—C10	178.2 (3)
C1—C2—C3—C4	0.9 (4)	C8—C9—C10—C11	0.3 (5)
Cl1—C2—C3—C4	−177.2 (2)	C9—C10—C11—C12	−1.3 (5)
C2—C3—C4—C5	−1.0 (4)	C9—C10—C11—C14	−179.8 (3)
C3—C4—C5—C6	−0.1 (4)	C10—C11—C12—C13	1.3 (4)
C4—C5—C6—C1	1.4 (4)	C14—C11—C12—C13	179.9 (3)
C4—C5—C6—Cl2	−178.2 (2)	C9—C8—C13—C12	−0.6 (4)
C2—C1—C6—C5	−1.5 (3)	C7—C8—C13—C12	−178.0 (2)
N1—C1—C6—C5	178.7 (2)	C11—C12—C13—C8	−0.4 (4)
C2—C1—C6—Cl2	178.09 (17)	O1—C7—N1—C1	−2.5 (3)
N1—C1—C6—Cl2	−1.7 (3)	C8—C7—N1—C1	177.2 (2)
O1—C7—C8—C9	−3.2 (4)	C2—C1—N1—C7	105.8 (3)
N1—C7—C8—C9	177.2 (2)	C6—C1—N1—C7	−74.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.82 (2)	2.08 (2)	2.878 (2)	164 (2)

Symmetry code: (i) −y+3/4, x+1/4, z+1/4.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁Cl₂NO
M_r	280.14
Crystal system, space group	Tetragonal, I4₁/a
Temperature (K)	293
a, c (Å)	16.4706 (8), 19.8709 (9)
V (Å³)	5390.6 (4)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.47
Crystal size (mm)	0.48 × 0.34 × 0.14

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.807, 0.937
No. of measured, independent and observed [I > 2σ(I)] reflections	5852, 2752, 1701
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.120, 1.01
No. of reflections	2752
No. of parameters	166
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.21

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.823 (16)	2.077 (17)	2.878 (2)	164 (2)

Symmetry code: (i) −y+3/4, x+1/4, z+1/4.

Acknowledgements

VZR thanks the University Grants Commission, Government of India, New Delhi, for award of an RFSMS research fellowship.

References

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