2-Chloro-N-(2,6-dimethyl­phen­yl)benzamide

Rodrigues, V.Z.; Gowda, B.T.; Sivý, J.; Vrábel, V.; Kožíšek, J.

doi:10.1107/S1600536812015607

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1408

doi:10.1107/S1600536812015607

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2-Chloro-N-(2,6-dimethylphenyl)benzamide

Vinola Z. Rodrigues,^a B. Thimme Gowda,^a ^* Július Sivý,^b Viktor Vrábel ^c and Jozef Kožíšek ^c

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, ^bInstitute of Mathematics and Physics, Faculty of Mechanical Engineering STU, Námestie Slobody 17, SK-812 37 Bratislava, Slovak Republic, and ^cInstitute of Physical Chemistry and Chemical Physics, Slovak University of Technology, Radlinského 9, SK-812 37 Bratislava, Slovak Republic
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 29 March 2012; accepted 10 April 2012; online 18 April 2012)

In the title compound, C₁₅H₁₄ClNO, the dihedral angle between the benzoyl and the aniline rings is 3.30 (18)°. In the crystal, N—H⋯O hydrogen bonds link the molecules into chains running along the a axis.

Related literature

For 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 , 2007 , 2008 ); Saeed et al. (2010 ), on N-chloroarylsulfonamides, see: Jyothi & Gowda (2004 ) and on N-bromoarylsulfonamides, see: Usha & Gowda (2006 ).

Experimental

Crystal data

C₁₅H₁₄ClNO
M_r = 259.72
Monoclinic, P 2₁ /n
a = 4.8322 (3) Å
b = 12.7817 (10) Å
c = 21.8544 (12) Å
β = 90.778 (5)°
V = 1349.69 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 295 K
0.51 × 0.30 × 0.11 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ), based on expressions derived by Clark & Reid (1995 )] T_min = 0.907, T_max = 0.971
18665 measured reflections
2469 independent reflections
1735 reflections with I > 2σ(I)
R_int = 0.081

Refinement

R[F² > 2σ(F²)] = 0.092
wR(F²) = 0.248
S = 1.12
2469 reflections
168 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86 (2)	1.96 (2)	2.818 (4)	172 (4)
Symmetry code: (i) x+1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ) and WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812015607/bt5865sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812015607/bt5865Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812015607/bt5865Isup3.cml

checkCIF report

Comment top

The amide and sulfonamide moieties are the constituents of many biologically important compounds. As part of studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Bowes et al., 2003; Gowda et al., 2000, 2007, 2008; Saeed et al., 2010), N-chloroarylsulfonamides (Jyothi & Gowda, 2004) and N-bromoarylsulfonamides (Usha & Gowda, 2006), in the present work, the crystal structure of 2-chloro-N-(2,6-dimethylphenyl)benzamide has been determined (Fig. 1).

In the title compound, one of the ortho-methyl groups in the aniline ring is positioned syn to the N—H bond, while the other ortho- methyl group is positioned anti to the N—H bond, the latter and the C=O bond being anti to each other. Further, the amide oxygen is syn to the ortho-chloro group in the benzoyl ring, similar to that observed in 2-chloro-N-(2,6-dichlorophenyl)benzamide (Gowda et al., 2008). In the title compound, the amide group forms dihedral angles of 63.26 (22)° and 59.88 (23)°, respectively, with the 2-chlorobenzoyl and the 2,6-dimethyl- anilino rings, while the angle between the benzoyl and the anilino rings is 3.46 (17)°.

In the crystal structure, intermolecular N1—H1···O1 hydrogen bonds (Table 1) link the molecules into infinite chains running along the a-axis. Part of the crystal structure is shown in Fig. 2.

Related literature top

For 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, 2007, 2008); Saeed et al. (2010), on N-chloroarylsulfonamides, see: Jyothi & Gowda (2004) and on N-bromoarylsulfonamides, see: Usha & Gowda (2006).

Experimental top

The title compound was prepared by a method similar to the one described by Gowda et al. (2008). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra.

Rod like colourless single crystals of the title compound used in the X-ray diffraction studies were obtained by slow evaporation of the solvent from its 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 CCD (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: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Molecular structure of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Packing view of the title compound. Molecular links along a-axis are generated by N–H···O hydrogen bonds which are shown by dashed lines. H atoms have been omitted for clarity.

2-Chloro-N-(2,6-dimethylphenyl)benzamide top

Crystal data top

C₁₅H₁₄ClNO	F(000) = 544
M_r = 259.72	D_x = 1.278 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3462 reflections
a = 4.8322 (3) Å	θ = 3.7–29.5°
b = 12.7817 (10) Å	µ = 0.27 mm⁻¹
c = 21.8544 (12) Å	T = 295 K
β = 90.778 (5)°	Rod, colourless
V = 1349.69 (15) Å³	0.51 × 0.30 × 0.11 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2469 independent reflections
Graphite monochromator	1735 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm^-1	R_int = 0.081
ω scans	θ_max = 25.3°, θ_min = 4.2°
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]	h = −5→5
T_min = 0.907, T_max = 0.971	k = −15→15
18665 measured reflections	l = −26→26

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)] = 0.092	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.248	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ²(F_o²) + (0.080P)² + 2.4052P] where P = (F_o² + 2F_c²)/3
2469 reflections	(Δ/σ)_max < 0.001
168 parameters	Δρ_max = 0.50 e Å⁻³
1 restraint	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₅H₁₄ClNO	V = 1349.69 (15) Å³
M_r = 259.72	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 4.8322 (3) Å	µ = 0.27 mm⁻¹
b = 12.7817 (10) Å	T = 295 K
c = 21.8544 (12) Å	0.51 × 0.30 × 0.11 mm
β = 90.778 (5)°

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2469 independent reflections
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]	1735 reflections with I > 2σ(I)
T_min = 0.907, T_max = 0.971	R_int = 0.081
18665 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.092	1 restraint
wR(F²) = 0.248	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	Δρ_max = 0.50 e Å⁻³
2469 reflections	Δρ_min = −0.27 e Å⁻³
168 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	0.5223 (8)	0.2456 (4)	0.47475 (19)	0.0494 (10)
C2	0.3612 (11)	0.3360 (4)	0.4743 (2)	0.0660 (13)
C3	0.3033 (14)	0.3824 (5)	0.5300 (3)	0.0892 (19)
H3	0.1927	0.4419	0.5307	0.107*
C4	0.4038 (14)	0.3431 (5)	0.5834 (3)	0.094 (2)
H4	0.3632	0.3761	0.6202	0.113*
C5	0.5672 (11)	0.2539 (5)	0.5836 (2)	0.0720 (15)
H5	0.6349	0.2271	0.6204	0.086*
C6	0.6293 (9)	0.2050 (4)	0.5296 (2)	0.0528 (11)
C7	0.8109 (11)	0.1086 (4)	0.5297 (2)	0.0720 (15)
H7A	0.8096	0.0771	0.5696	0.108*
H7B	0.9967	0.1281	0.5197	0.108*
H7C	0.7417	0.0596	0.5	0.108*
C8	0.2532 (14)	0.3832 (4)	0.4152 (3)	0.0830 (17)
H8A	0.2349	0.4575	0.42	0.124*
H8B	0.0759	0.3534	0.4052	0.124*
H8C	0.3803	0.3685	0.3829	0.124*
C9	0.3874 (8)	0.1464 (3)	0.38474 (18)	0.0438 (10)
C10	0.4897 (8)	0.0847 (4)	0.3306 (2)	0.0533 (11)
C11	0.6640 (10)	0.0015 (4)	0.3394 (2)	0.0661 (13)
H11	0.7286	−0.0141	0.3786	0.079*
C12	0.7455 (13)	−0.0601 (5)	0.2903 (3)	0.0911 (19)
H12	0.8633	−0.1166	0.2968	0.109*
C13	0.6524 (15)	−0.0373 (6)	0.2326 (3)	0.097 (2)
H13	0.7055	−0.0789	0.1998	0.116*
C14	0.4789 (14)	0.0476 (6)	0.2226 (3)	0.0887 (19)
H14	0.4174	0.0643	0.1833	0.106*
C15	0.3997 (10)	0.1063 (4)	0.2718 (2)	0.0649 (13)
N1	0.5818 (7)	0.1927 (3)	0.41875 (15)	0.0460 (9)
H1	0.756 (4)	0.180 (4)	0.415 (2)	0.055*
O1	0.1424 (6)	0.1494 (3)	0.39531 (15)	0.0656 (10)
Cl1	0.1880 (4)	0.21406 (14)	0.25687 (7)	0.0994 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.050 (2)	0.053 (3)	0.045 (2)	0.0038 (19)	0.0043 (18)	−0.0021 (19)
C2	0.079 (3)	0.063 (3)	0.057 (3)	0.019 (3)	0.001 (2)	0.000 (2)
C3	0.119 (5)	0.076 (4)	0.073 (4)	0.039 (4)	0.007 (3)	−0.022 (3)
C4	0.127 (5)	0.096 (5)	0.061 (4)	0.029 (4)	0.013 (3)	−0.028 (3)
C5	0.086 (3)	0.089 (4)	0.041 (3)	0.002 (3)	−0.001 (2)	−0.006 (3)
C6	0.056 (2)	0.056 (3)	0.046 (2)	0.004 (2)	0.0018 (19)	−0.002 (2)
C7	0.079 (3)	0.082 (4)	0.055 (3)	0.018 (3)	−0.009 (2)	0.007 (3)
C8	0.118 (5)	0.065 (3)	0.066 (3)	0.033 (3)	−0.004 (3)	0.006 (3)
C9	0.041 (2)	0.052 (3)	0.039 (2)	0.0011 (18)	−0.0020 (16)	0.0078 (18)
C10	0.042 (2)	0.070 (3)	0.048 (2)	−0.005 (2)	0.0017 (18)	−0.005 (2)
C11	0.061 (3)	0.070 (3)	0.067 (3)	0.001 (3)	0.002 (2)	−0.016 (3)
C12	0.087 (4)	0.079 (4)	0.107 (5)	0.007 (3)	0.012 (4)	−0.036 (4)
C13	0.110 (5)	0.108 (5)	0.073 (4)	−0.019 (4)	0.020 (4)	−0.046 (4)
C14	0.101 (4)	0.112 (5)	0.053 (3)	−0.019 (4)	0.000 (3)	−0.019 (3)
C15	0.068 (3)	0.074 (3)	0.052 (3)	−0.012 (3)	0.004 (2)	−0.003 (2)
N1	0.0393 (17)	0.056 (2)	0.0428 (19)	0.0052 (16)	0.0047 (15)	−0.0015 (16)
O1	0.0413 (17)	0.093 (3)	0.062 (2)	0.0015 (16)	0.0020 (14)	−0.0100 (18)
Cl1	0.1313 (14)	0.1054 (13)	0.0612 (9)	0.0210 (10)	−0.0121 (8)	0.0189 (8)

Geometric parameters (Å, º) top

C1—C2	1.394 (6)	C8—H8C	0.96
C1—C6	1.398 (6)	C9—O1	1.210 (5)
C1—N1	1.431 (5)	C9—N1	1.329 (5)
C2—C3	1.386 (7)	C9—C10	1.511 (6)
C2—C8	1.511 (7)	C10—C11	1.369 (7)
C3—C4	1.355 (9)	C10—C15	1.379 (7)
C3—H3	0.93	C11—C12	1.392 (8)
C4—C5	1.387 (8)	C11—H11	0.93
C4—H4	0.93	C12—C13	1.365 (10)
C5—C6	1.373 (7)	C12—H12	0.93
C5—H5	0.93	C13—C14	1.387 (9)
C6—C7	1.512 (7)	C13—H13	0.93
C7—H7A	0.96	C14—C15	1.370 (8)
C7—H7B	0.96	C14—H14	0.93
C7—H7C	0.96	C15—Cl1	1.744 (6)
C8—H8A	0.96	N1—H1	0.860 (19)
C8—H8B	0.96

C2—C1—C6	120.9 (4)	C2—C8—H8C	109.5
C2—C1—N1	120.3 (4)	H8A—C8—H8C	109.5
C6—C1—N1	118.8 (4)	H8B—C8—H8C	109.5
C3—C2—C1	117.9 (5)	O1—C9—N1	124.4 (4)
C3—C2—C8	120.6 (5)	O1—C9—C10	119.8 (4)
C1—C2—C8	121.5 (4)	N1—C9—C10	115.7 (3)
C4—C3—C2	121.6 (5)	C11—C10—C15	118.2 (5)
C4—C3—H3	119.2	C11—C10—C9	120.2 (4)
C2—C3—H3	119.2	C15—C10—C9	121.6 (4)
C3—C4—C5	120.2 (5)	C10—C11—C12	120.7 (6)
C3—C4—H4	119.9	C10—C11—H11	119.6
C5—C4—H4	119.9	C12—C11—H11	119.6
C6—C5—C4	120.3 (5)	C13—C12—C11	119.9 (6)
C6—C5—H5	119.9	C13—C12—H12	120
C4—C5—H5	119.9	C11—C12—H12	120
C5—C6—C1	119.0 (4)	C12—C13—C14	120.2 (6)
C5—C6—C7	120.2 (4)	C12—C13—H13	119.9
C1—C6—C7	120.8 (4)	C14—C13—H13	119.9
C6—C7—H7A	109.5	C15—C14—C13	118.7 (6)
C6—C7—H7B	109.5	C15—C14—H14	120.7
H7A—C7—H7B	109.5	C13—C14—H14	120.7
C6—C7—H7C	109.5	C14—C15—C10	122.3 (6)
H7A—C7—H7C	109.5	C14—C15—Cl1	117.1 (5)
H7B—C7—H7C	109.5	C10—C15—Cl1	120.6 (4)
C2—C8—H8A	109.5	C9—N1—C1	122.7 (3)
C2—C8—H8B	109.5	C9—N1—H1	124 (3)
H8A—C8—H8B	109.5	C1—N1—H1	112 (3)

C6—C1—C2—C3	−2.0 (8)	N1—C9—C10—C15	−122.9 (5)
N1—C1—C2—C3	178.2 (5)	C15—C10—C11—C12	−0.6 (7)
C6—C1—C2—C8	177.6 (5)	C9—C10—C11—C12	175.8 (5)
N1—C1—C2—C8	−2.2 (8)	C10—C11—C12—C13	0.3 (9)
C1—C2—C3—C4	1.4 (10)	C11—C12—C13—C14	0.6 (10)
C8—C2—C3—C4	−178.2 (7)	C12—C13—C14—C15	−1.2 (10)
C2—C3—C4—C5	−0.6 (11)	C13—C14—C15—C10	0.9 (9)
C3—C4—C5—C6	0.3 (10)	C13—C14—C15—Cl1	178.6 (5)
C4—C5—C6—C1	−0.9 (8)	C11—C10—C15—C14	0.0 (7)
C4—C5—C6—C7	179.1 (5)	C9—C10—C15—C14	−176.4 (5)
C2—C1—C6—C5	1.8 (7)	C11—C10—C15—Cl1	−177.6 (4)
N1—C1—C6—C5	−178.4 (4)	C9—C10—C15—Cl1	6.0 (6)
C2—C1—C6—C7	−178.2 (5)	O1—C9—N1—C1	4.6 (7)
N1—C1—C6—C7	1.6 (7)	C10—C9—N1—C1	−173.9 (4)
O1—C9—C10—C11	−117.8 (5)	C2—C1—N1—C9	−65.8 (6)
N1—C9—C10—C11	60.8 (6)	C6—C1—N1—C9	114.4 (5)
O1—C9—C10—C15	58.5 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86 (2)	1.96 (2)	2.818 (4)	172 (4)

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄ClNO
M_r	259.72
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	4.8322 (3), 12.7817 (10), 21.8544 (12)
β (°)	90.778 (5)
V (Å³)	1349.69 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.51 × 0.30 × 0.11

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction	Analytical [CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]
T_min, T_max	0.907, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	18665, 2469, 1735
R_int	0.081
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.092, 0.248, 1.12
No. of reflections	2469
No. of parameters	168
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)	0.50, −0.27

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.860 (19)	1.96 (2)	2.818 (4)	172 (4)

Symmetry code: (i) x+1, y, z.

Acknowledgements

VZR thanks the University Grants Commission, Government of India, New Delhi for award of an RFSMS research fellowship. JS, VV and JK thank the Grant Agencies for their financial support (VEGA Grant Agency of Slovak Ministry of Education 1/0679/11; Research and Development Agency of Slovakia (APVV-0202–10) and the Structural Funds, Interreg IIIA, for financial support in purchasing the diffractometer.

References

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