2-Chloro-N-(2-methyl­phen­yl)benzamide

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

doi:10.1107/S1600536812023902

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1936

doi:10.1107/S1600536812023902

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2-Chloro-N-(2-methylphenyl)benzamide

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

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

(Received 24 May 2012; accepted 25 May 2012; online 31 May 2012)

In the title compound, C₁₄H₁₂ClNO, the two aromatic rings are almost coplanar, making a dihedral angle of 4.08 (18)°. In the crystal, N—H⋯O hydrogen bonds link the molecules into infinite 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 ); Rodrigues et al. (2012 ); Saeed et al. (2010 ) of N-chloroarylamides, see: Gowda & Rao (1989 ); Jyothi & Gowda (2004 ) and of N-bromoarylsulfonamides, see: Gowda & Mahadevappa (1983 ); Usha & Gowda (2006 ).

Experimental

Crystal data

C₁₄H₁₂ClNO
M_r = 245.70
Orthorhombic, P n a 2₁
a = 9.746 (3) Å
b = 6.077 (3) Å
c = 20.797 (7) Å
V = 1231.8 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 295 K
0.55 × 0.40 × 0.25 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 = 0.865, T_max = 0.921
16249 measured reflections
2173 independent reflections
1369 reflections with I > 2σ(I)
R_int = 0.097

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.147
S = 1.10
2173 reflections
158 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.14 e Å⁻³
Absolute structure: Flack (1983 ), 1054 Friedel pairs
Flack parameter: 0.37 (13)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86 (1)	2.00 (1)	2.853 (5)	171 (5)
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ .

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: DIAMOND (Brandenburg, 2002 ); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ) and WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812023902/bt5935sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812023902/bt5935Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812023902/bt5935Isup3.cml

checkCIF report

Comment top

The amide and sulfonamide moieties are the constituents of many biologically important compounds. As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Bowes et al., 2003; Gowda et al., 2000; Rodrigues et al., 2012; Saeed et al., 2010), N-chloroarylsulfonamides(Gowda & Rao, 1989; Jyothi & Gowda, 2004) and N-bromoarylsulfonamides(Gowda & Mahadevappa, 1983; Usha & Gowda, 2006), in the present work, the crystal structure of 2-chloro-N-(2-methylphenyl)benzamide has been determined (Fig.1).

In the title compound, the ortho-Cl atom in the benzoyl ring is positioned syn to the C=O bond, similar to that observed in 2-chloro-N-(3-methylphenyl)benzamide (I) (Rodrigues et al., 2012). The ortho-methyl group in the anilino ring is also positioned syn to the N—H bond, in contrast to the anti conformation observed between the meta-methyl group and the N—H bond in (I).

The central amide core –NH—C(=O)– group is twisted by 58.77 (27)° and 56.30 (28)° out of the planes of the 2-chlorophenyl and 2-methylphenyl rings, respectively, while the two aromatic rings make only a dihedral angle of 4.08 (18)°, compared to the value of 38.7 (1)° in (I)

In the crystal structure, intermolecular N—H···O 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); Rodrigues et al. (2012); Saeed et al. (2010); N-chloroarylamides, see: Gowda & Rao (1989), Jyothi & Gowda (2004) and N-bromoarylsulfonamides, see: Gowda & Mahadevappa (1983), Usha & Gowda (2006).

Experimental top

The title compound was prepared by the method similar to the one described by Gowda et al. (2000). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra.

Plate like colorless single crystals of the title compound used in X-ray diffraction studies were obtained by slow evaporation of 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 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: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), 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-methylphenyl)benzamide top

Crystal data top

C₁₄H₁₂ClNO	F(000) = 512
M_r = 245.70	D_x = 1.325 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2182 reflections
a = 9.746 (3) Å	θ = 3.5–25.0°
b = 6.077 (3) Å	µ = 0.29 mm⁻¹
c = 20.797 (7) Å	T = 295 K
V = 1231.8 (8) Å³	Plate, colourless
Z = 4	0.55 × 0.40 × 0.25 mm

Data collection top

Xcalibur, Ruby, Gemini diffractometer	2173 independent reflections
Radiation source: fine-focus sealed tube	1369 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.097
Detector resolution: 10.434 pixels mm^-1	θ_max = 25.0°, θ_min = 3.5°
ω scans	h = −11→11
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]	k = −7→7
T_min = 0.865, T_max = 0.921	l = −24→24
16249 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.068	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.147	w = 1/[σ²(F_o²) + (0.058P)²] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max < 0.001
2173 reflections	Δρ_max = 0.22 e Å⁻³
158 parameters	Δρ_min = −0.14 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 1054 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.37 (13)

Crystal data top

C₁₄H₁₂ClNO	V = 1231.8 (8) Å³
M_r = 245.70	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 9.746 (3) Å	µ = 0.29 mm⁻¹
b = 6.077 (3) Å	T = 295 K
c = 20.797 (7) Å	0.55 × 0.40 × 0.25 mm

Data collection top

Xcalibur, Ruby, Gemini diffractometer	2173 independent reflections
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]	1369 reflections with I > 2σ(I)
T_min = 0.865, T_max = 0.921	R_int = 0.097
16249 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.147	Δρ_max = 0.22 e Å⁻³
S = 1.10	Δρ_min = −0.14 e Å⁻³
2173 reflections	Absolute structure: Flack (1983), 1054 Friedel pairs
158 parameters	Absolute structure parameter: 0.37 (13)
2 restraints

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	0.5638 (4)	0.6837 (8)	0.4527 (3)	0.0506 (12)
C2	0.5037 (4)	0.5445 (10)	0.3997 (2)	0.0497 (14)
C3	0.5364 (4)	0.5696 (9)	0.3373 (3)	0.0596 (15)
C4	0.4845 (7)	0.4319 (12)	0.2916 (3)	0.0833 (19)
H4A	0.5099	0.4492	0.2488	0.100*
C5	0.3941 (6)	0.2667 (12)	0.3087 (5)	0.0850 (17)
H5A	0.3587	0.1723	0.2777	0.102*
C6	0.3578 (5)	0.2439 (10)	0.3713 (4)	0.0784 (17)
H6A	0.2968	0.1338	0.3834	0.094*
C7	0.4101 (4)	0.3811 (10)	0.4159 (3)	0.0644 (16)
H7A	0.3830	0.3660	0.4585	0.077*
C8	0.5196 (4)	0.9375 (9)	0.5395 (3)	0.0552 (14)
C9	0.4657 (5)	0.9069 (10)	0.6004 (3)	0.0646 (16)
C10	0.5118 (6)	1.0562 (13)	0.6480 (3)	0.0815 (18)
H10A	0.4756	1.0470	0.6893	0.098*
C11	0.6062 (7)	1.2098 (13)	0.6351 (4)	0.096 (3)
H11A	0.6403	1.2963	0.6684	0.115*
C12	0.6535 (5)	1.2420 (9)	0.5735 (4)	0.0813 (19)
H12A	0.7152	1.3549	0.5647	0.098*
C13	0.6101 (4)	1.1096 (10)	0.5260 (3)	0.0679 (17)
H13A	0.6402	1.1324	0.4841	0.082*
C14	0.3642 (5)	0.7289 (9)	0.6169 (3)	0.0664 (16)
H14C	0.3400	0.7395	0.6615	0.100*
H14B	0.4044	0.5875	0.6086	0.100*
H14A	0.2833	0.7461	0.5910	0.100*
N1	0.4759 (4)	0.7929 (8)	0.4882 (2)	0.0611 (12)
H1	0.3902 (14)	0.785 (9)	0.479 (3)	0.070 (17)*
O1	0.6897 (3)	0.6844 (6)	0.46020 (18)	0.0739 (11)
Cl1	0.64973 (16)	0.7710 (3)	0.31282 (10)	0.0971 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.042 (2)	0.046 (3)	0.063 (3)	0.001 (2)	−0.005 (2)	−0.001 (3)
C2	0.029 (2)	0.071 (4)	0.049 (3)	0.006 (2)	−0.002 (2)	−0.002 (2)
C3	0.044 (3)	0.076 (4)	0.059 (4)	0.006 (2)	0.000 (3)	−0.003 (3)
C4	0.088 (4)	0.102 (6)	0.060 (4)	0.024 (4)	−0.003 (3)	−0.011 (4)
C5	0.076 (4)	0.082 (4)	0.097 (5)	0.004 (3)	−0.012 (4)	−0.035 (4)
C6	0.064 (4)	0.078 (5)	0.093 (5)	−0.010 (3)	−0.004 (3)	−0.020 (4)
C7	0.042 (3)	0.081 (4)	0.070 (4)	−0.004 (2)	0.001 (2)	−0.004 (3)
C8	0.036 (2)	0.063 (4)	0.067 (4)	0.010 (3)	−0.011 (3)	−0.017 (3)
C9	0.054 (3)	0.074 (4)	0.066 (4)	0.020 (3)	−0.015 (3)	−0.011 (4)
C10	0.065 (3)	0.114 (6)	0.065 (4)	0.020 (4)	−0.002 (3)	−0.010 (4)
C11	0.090 (5)	0.104 (6)	0.094 (6)	0.015 (4)	−0.028 (4)	−0.049 (5)
C12	0.061 (3)	0.067 (4)	0.116 (6)	0.001 (3)	−0.015 (3)	−0.023 (4)
C13	0.046 (3)	0.077 (5)	0.080 (4)	0.002 (3)	−0.003 (3)	−0.006 (4)
C14	0.059 (3)	0.069 (4)	0.071 (4)	−0.001 (3)	−0.006 (2)	0.015 (3)
N1	0.039 (2)	0.082 (3)	0.062 (3)	0.002 (2)	−0.005 (2)	0.002 (3)
O1	0.0306 (15)	0.100 (3)	0.091 (2)	0.0024 (15)	−0.0065 (16)	−0.020 (2)
Cl1	0.0948 (11)	0.1063 (14)	0.0900 (10)	−0.0151 (10)	0.0021 (11)	0.0281 (10)

Geometric parameters (Å, º) top

C1—O1	1.237 (5)	C8—C13	1.396 (7)
C1—N1	1.311 (6)	C8—N1	1.446 (6)
C1—C2	1.507 (7)	C9—C10	1.416 (8)
C2—C3	1.346 (6)	C9—C14	1.506 (8)
C2—C7	1.389 (7)	C10—C11	1.337 (10)
C3—C4	1.364 (7)	C10—H10A	0.9300
C3—Cl1	1.725 (6)	C11—C12	1.377 (10)
C4—C5	1.382 (9)	C11—H11A	0.9300
C4—H4A	0.9300	C12—C13	1.342 (8)
C5—C6	1.356 (11)	C12—H12A	0.9300
C5—H5A	0.9300	C13—H13A	0.9300
C6—C7	1.347 (8)	C14—H14C	0.9600
C6—H6A	0.9300	C14—H14B	0.9600
C7—H7A	0.9300	C14—H14A	0.9600
C8—C9	1.384 (7)	N1—H1	0.861 (2)

O1—C1—N1	125.1 (4)	C8—C9—C10	115.7 (6)
O1—C1—C2	118.7 (4)	C8—C9—C14	123.7 (5)
N1—C1—C2	116.2 (4)	C10—C9—C14	120.6 (5)
C3—C2—C7	118.0 (5)	C11—C10—C9	121.7 (6)
C3—C2—C1	123.3 (5)	C11—C10—H10A	119.2
C7—C2—C1	118.7 (5)	C9—C10—H10A	119.2
C2—C3—C4	121.0 (5)	C10—C11—C12	121.1 (7)
C2—C3—Cl1	121.1 (4)	C10—C11—H11A	119.5
C4—C3—Cl1	117.9 (5)	C12—C11—H11A	119.5
C3—C4—C5	120.2 (6)	C13—C12—C11	119.6 (6)
C3—C4—H4A	119.9	C13—C12—H12A	120.2
C5—C4—H4A	119.9	C11—C12—H12A	120.2
C6—C5—C4	119.2 (7)	C12—C13—C8	120.1 (6)
C6—C5—H5A	120.4	C12—C13—H13A	120.0
C4—C5—H5A	120.4	C8—C13—H13A	120.0
C7—C6—C5	119.9 (6)	C9—C14—H14C	109.5
C7—C6—H6A	120.1	C9—C14—H14B	109.5
C5—C6—H6A	120.1	H14C—C14—H14B	109.5
C6—C7—C2	121.6 (6)	C9—C14—H14A	109.5
C6—C7—H7A	119.2	H14C—C14—H14A	109.5
C2—C7—H7A	119.2	H14B—C14—H14A	109.5
C9—C8—C13	121.6 (5)	C1—N1—C8	122.0 (4)
C9—C8—N1	118.8 (5)	C1—N1—H1	118 (4)
C13—C8—N1	119.6 (5)	C8—N1—H1	120 (4)

O1—C1—C2—C3	−59.1 (7)	C13—C8—C9—C10	−2.0 (7)
N1—C1—C2—C3	122.1 (5)	N1—C8—C9—C10	−179.2 (4)
O1—C1—C2—C7	120.7 (5)	C13—C8—C9—C14	177.8 (5)
N1—C1—C2—C7	−58.2 (6)	N1—C8—C9—C14	0.6 (7)
C7—C2—C3—C4	−3.2 (8)	C8—C9—C10—C11	−2.9 (9)
C1—C2—C3—C4	176.6 (4)	C14—C9—C10—C11	177.2 (6)
C7—C2—C3—Cl1	179.0 (4)	C9—C10—C11—C12	5.8 (10)
C1—C2—C3—Cl1	−1.2 (7)	C10—C11—C12—C13	−3.6 (10)
C2—C3—C4—C5	1.6 (8)	C11—C12—C13—C8	−1.3 (8)
Cl1—C3—C4—C5	179.5 (5)	C9—C8—C13—C12	4.2 (8)
C3—C4—C5—C6	0.2 (9)	N1—C8—C13—C12	−178.7 (4)
C4—C5—C6—C7	−0.3 (9)	O1—C1—N1—C8	3.0 (7)
C5—C6—C7—C2	−1.4 (9)	C2—C1—N1—C8	−178.3 (5)
C3—C2—C7—C6	3.1 (8)	C9—C8—N1—C1	−126.3 (5)
C1—C2—C7—C6	−176.7 (5)	C13—C8—N1—C1	56.4 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86 (1)	2.00 (1)	2.853 (5)	171 (5)

Symmetry code: (i) x−1/2, −y+3/2, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂ClNO
M_r	245.70
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	295
a, b, c (Å)	9.746 (3), 6.077 (3), 20.797 (7)
V (Å³)	1231.8 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.55 × 0.40 × 0.25

Data collection
Diffractometer	Xcalibur, Ruby, Gemini diffractometer
Absorption correction	Analytical [CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]
T_min, T_max	0.865, 0.921
No. of measured, independent and observed [I > 2σ(I)] reflections	16249, 2173, 1369
R_int	0.097
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.147, 1.10
No. of reflections	2173
No. of parameters	158
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.14
Absolute structure	Flack (1983), 1054 Friedel pairs
Absolute structure parameter	0.37 (13)

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis CCD, CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2002), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.861 (2)	2.000 (10)	2.853 (5)	171 (5)

Symmetry code: (i) x−1/2, −y+3/2, z.

Acknowledgements

VZR thanks the University Grants Commission, Government of India, New Delhi, for the award of an RFSMS research fellowship. JS, VV and JK thank the Grant Agencies for their financial support [VEGA Grant Agency of the Slovak Ministry of Education (1/0679/11) and the 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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