4-Chloro-N-(3-methyl­phen­yl)benzamide

Rodrigues, V.Z.; Fronc, M.; Gowda, B.T.; Kožíšek, J.

doi:10.1107/S1600536811040864

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2903

doi:10.1107/S1600536811040864

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4-Chloro-N-(3-methylphenyl)benzamide

Vinola Z. Rodrigues,^a Marek Fronc,^b B. Thimme Gowda ^a ^* and Jozef Kožíšek ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute 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 2 October 2011; accepted 4 October 2011; online 8 October 2011)

In the title compound, C₁₄H₁₂ClNO, the meta-methyl substituent in the aniline ring is positioned anti to the N—H bond. The dihedral angle between the rings is 12.4 (1)°. The crystal structure is stabilized by intermolecular N—H⋯O hydrogen bonds, which link the molecules into C(4) chains running along the c-axis direction.

Related literature

For the preparation of the title compound, see: Gowda et al. (2003 ). 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 ); Saeed et al. (2010 ), on N-(aryl)-methanesulfonamides, see: Gowda et al. (2007 ), on N-(aryl)-arylsulfonamides, see: Shetty & Gowda (2005 ) and on N-chloro-arylsulfonamides, see: Gowda & Shetty (2004 ).

Experimental

Crystal data

C₁₄H₁₂ClNO
M_r = 245.70
Monoclinic, P 2₁ /c
a = 13.4379 (9) Å
b = 10.2493 (11) Å
c = 9.2600 (7) Å
β = 92.893 (6)°
V = 1273.74 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 293 K
0.81 × 0.17 × 0.04 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector
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 from Clark & Reid (1995 )] T_min = 0.877, T_max = 0.988
17187 measured reflections
2156 independent reflections
1299 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.117
S = 0.94
2156 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.86	2.06	2.888 (2)	161
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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: Mercury (Macrae et al., 2008 ); software used to prepare material for publication: enCIFer (Allen et al., 2004 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811040864/bt5661sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811040864/bt5661Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811040864/bt5661Isup3.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; Saeed et al., 2010), N-(aryl)-methanesulfonamides (Gowda et al., 2007), N-(aryl)-arylsulfonamides (Shetty & Gowda, 2005) and N-chloro-arylsulfonamides (Gowda & Shetty, 2004), in the present work, the crystal structure of 4-chloro-N-(3-methylphenyl)benzamide (I) has been determined (Fig.1). In (I), the meta-methyl substituent in the anilino ring is positioned anti to the N–H bond.

The central amide group –NHCO– is tilted to the anilino ring with the C9—C8—N1—C7 and C13—C8—N1—C7 torsion angles of 30.4 (3)° and -151.2 (2)°. The C2—C1—C7—N1 and C6—C1—C7—N1 torsion angles are -15.7 (3)° and 166.8 (2)°, respectively, while the C2—C1—C7—O1 and C6—C1—C7—O1 torsion angles are 162.8 (2)° and -14.7 (3)°, respectively. But the C1—C7—N1—C8 and C8—N1—C7—O1 torsion angles are 173.6 (2)° and -4.9 (3)°, respectively.

The packing of molecules linked by N—H···O hydrogen bonds is shown in Fig. 2.

Related literature top

For the preparation of the title compound, see: Gowda et al. (2003). 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); Saeed et al. (2010), on N-(aryl)-methanesulfonamides, see: Gowda et al. (2007), on N-(aryl)-arylsulfonamides, see: Shetty & Gowda (2005) and on N-chloro-arylsulfonamides, see: Gowda & Shetty (2004).

Experimental top

The title compound was prepared according to the method described by Gowda et al. (2003). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra. Plate like colourless single crystals of the title compound 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 (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: Mercury (Macrae et al., 2008); software used to prepare material for publication: enCIFer (Allen et al., 2004).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Part of the crystal structure of the title compound generated by N—H···O hydrogen bonds which are shown by dashed lines. H atoms not involved in intermolecular bonding have been omitted.

4-Chloro-N-(3-methylphenyl)benzamide top

Crystal data top

C₁₄H₁₂ClNO	F(000) = 512
M_r = 245.70	D_x = 1.281 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2ybc	Cell parameters from 4939 reflections
a = 13.4379 (9) Å	θ = 3.4–29.4°
b = 10.2493 (11) Å	µ = 0.28 mm⁻¹
c = 9.2600 (7) Å	T = 293 K
β = 92.893 (6)°	Plate, colorless
V = 1273.74 (19) Å³	0.81 × 0.17 × 0.04 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector	2156 independent reflections
Radiation source: fine-focus sealed tube	1299 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ω scans	θ_max = 24.7°, θ_min = 4.2°
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived from Clark & Reid (1995)]	h = −15→15
T_min = 0.877, T_max = 0.988	k = −12→12
17187 measured reflections	l = −10→10

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 0.94	w = 1/[σ²(F_o²) + (0.0699P)²] where P = (F_o² + 2F_c²)/3
2156 reflections	(Δ/σ)_max < 0.001
154 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₁₄H₁₂ClNO	V = 1273.74 (19) Å³
M_r = 245.70	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.4379 (9) Å	µ = 0.28 mm⁻¹
b = 10.2493 (11) Å	T = 293 K
c = 9.2600 (7) Å	0.81 × 0.17 × 0.04 mm
β = 92.893 (6)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector	2156 independent reflections
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived from Clark & Reid (1995)]	1299 reflections with I > 2σ(I)
T_min = 0.877, T_max = 0.988	R_int = 0.040
17187 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 0.94	Δρ_max = 0.22 e Å⁻³
2156 reflections	Δρ_min = −0.13 e Å⁻³
154 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
C1	0.44789 (14)	0.3375 (2)	−0.05692 (18)	0.0570 (5)
C2	0.40134 (16)	0.2716 (2)	0.0505 (2)	0.0749 (6)
H2A	0.4350	0.2045	0.0999	0.090*
C3	0.30600 (17)	0.3031 (3)	0.0860 (3)	0.0850 (7)
H3A	0.2759	0.2590	0.1600	0.102*
C4	0.25583 (15)	0.4008 (3)	0.0105 (3)	0.0746 (6)
C5	0.30042 (16)	0.4691 (2)	−0.0950 (2)	0.0715 (6)
H5A	0.2665	0.5361	−0.1441	0.086*
C6	0.39659 (15)	0.4374 (2)	−0.1280 (2)	0.0651 (6)
H6A	0.4274	0.4841	−0.1994	0.078*
C7	0.54954 (14)	0.3041 (2)	−0.10552 (19)	0.0587 (5)
C8	0.70086 (15)	0.1721 (2)	−0.0475 (2)	0.0636 (6)
C9	0.76789 (15)	0.2328 (2)	−0.1344 (2)	0.0695 (6)
H9A	0.7512	0.3126	−0.1768	0.083*
C10	0.85939 (16)	0.1769 (3)	−0.1594 (2)	0.0806 (7)
C11	0.88194 (19)	0.0584 (3)	−0.0961 (3)	0.0932 (8)
H11A	0.9423	0.0185	−0.1139	0.112*
C12	0.8172 (2)	−0.0028 (3)	−0.0066 (3)	0.0966 (8)
H12A	0.8347	−0.0820	0.0366	0.116*
C13	0.72518 (18)	0.0546 (3)	0.0188 (2)	0.0811 (7)
H13A	0.6812	0.0144	0.0793	0.097*
C14	0.93185 (19)	0.2429 (3)	−0.2533 (3)	0.1117 (10)
H14C	0.9906	0.1900	−0.2584	0.134*
H14B	0.9496	0.3265	−0.2129	0.134*
H14A	0.9018	0.2544	−0.3487	0.134*
N1	0.60639 (12)	0.22675 (17)	−0.01846 (16)	0.0636 (5)
H1A	0.5833	0.2081	0.0640	0.076*
O1	0.57677 (10)	0.34502 (16)	−0.22211 (13)	0.0762 (5)
Cl1	0.13343 (4)	0.43547 (8)	0.04942 (9)	0.1151 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0537 (11)	0.0700 (14)	0.0472 (10)	−0.0039 (11)	0.0032 (8)	−0.0056 (10)
C2	0.0575 (13)	0.0910 (17)	0.0767 (14)	0.0007 (11)	0.0087 (11)	0.0183 (12)
C3	0.0605 (14)	0.108 (2)	0.0887 (16)	−0.0038 (14)	0.0215 (12)	0.0212 (14)
C4	0.0506 (12)	0.0875 (17)	0.0864 (14)	−0.0042 (11)	0.0101 (11)	−0.0100 (13)
C5	0.0633 (13)	0.0758 (16)	0.0751 (13)	0.0058 (11)	0.0019 (11)	−0.0011 (11)
C6	0.0650 (13)	0.0747 (15)	0.0562 (11)	−0.0025 (11)	0.0096 (10)	−0.0003 (10)
C7	0.0562 (12)	0.0761 (14)	0.0438 (10)	−0.0039 (10)	0.0031 (9)	−0.0071 (9)
C8	0.0598 (12)	0.0813 (16)	0.0498 (10)	0.0084 (11)	0.0022 (9)	−0.0116 (11)
C9	0.0598 (13)	0.0931 (17)	0.0558 (11)	0.0087 (12)	0.0043 (10)	−0.0080 (10)
C10	0.0590 (14)	0.123 (2)	0.0590 (12)	0.0198 (14)	−0.0026 (10)	−0.0145 (13)
C11	0.0670 (15)	0.131 (3)	0.0807 (15)	0.0254 (16)	−0.0042 (13)	−0.0256 (17)
C12	0.091 (2)	0.095 (2)	0.1014 (19)	0.0246 (16)	−0.0190 (16)	−0.0062 (15)
C13	0.0794 (16)	0.0897 (19)	0.0739 (14)	0.0095 (14)	0.0015 (12)	−0.0021 (13)
C14	0.0646 (15)	0.179 (3)	0.0930 (17)	0.0155 (17)	0.0231 (13)	−0.0068 (17)
N1	0.0575 (10)	0.0846 (13)	0.0494 (9)	0.0063 (9)	0.0104 (7)	−0.0001 (8)
O1	0.0624 (8)	0.1183 (13)	0.0485 (8)	0.0053 (8)	0.0093 (6)	0.0064 (8)
Cl1	0.0586 (4)	0.1374 (7)	0.1517 (7)	0.0078 (4)	0.0288 (4)	0.0031 (5)

Geometric parameters (Å, º) top

C1—C2	1.378 (3)	C8—C9	1.386 (3)
C1—C6	1.382 (3)	C8—N1	1.426 (3)
C1—C7	1.499 (3)	C9—C10	1.387 (3)
C2—C3	1.377 (3)	C9—H9A	0.9300
C2—H2A	0.9300	C10—C11	1.375 (4)
C3—C4	1.378 (3)	C10—C14	1.499 (4)
C3—H3A	0.9300	C11—C12	1.382 (4)
C4—C5	1.365 (3)	C11—H11A	0.9300
C4—Cl1	1.738 (2)	C12—C13	1.400 (4)
C5—C6	1.381 (3)	C12—H12A	0.9300
C5—H5A	0.9300	C13—H13A	0.9300
C6—H6A	0.9300	C14—H14C	0.9600
C7—O1	1.231 (2)	C14—H14B	0.9600
C7—N1	1.342 (2)	C14—H14A	0.9600
C8—C13	1.383 (3)	N1—H1A	0.8600

C2—C1—C6	118.24 (19)	C8—C9—C10	121.3 (2)
C2—C1—C7	123.92 (19)	C8—C9—H9A	119.4
C6—C1—C7	117.79 (17)	C10—C9—H9A	119.4
C3—C2—C1	121.3 (2)	C11—C10—C9	118.2 (2)
C3—C2—H2A	119.4	C11—C10—C14	120.7 (2)
C1—C2—H2A	119.4	C9—C10—C14	121.2 (3)
C2—C3—C4	119.1 (2)	C10—C11—C12	121.6 (2)
C2—C3—H3A	120.4	C10—C11—H11A	119.2
C4—C3—H3A	120.4	C12—C11—H11A	119.2
C5—C4—C3	121.0 (2)	C11—C12—C13	119.9 (3)
C5—C4—Cl1	119.86 (19)	C11—C12—H12A	120.0
C3—C4—Cl1	119.17 (18)	C13—C12—H12A	120.0
C4—C5—C6	119.1 (2)	C8—C13—C12	118.8 (2)
C4—C5—H5A	120.4	C8—C13—H13A	120.6
C6—C5—H5A	120.4	C12—C13—H13A	120.6
C5—C6—C1	121.23 (19)	C10—C14—H14C	109.5
C5—C6—H6A	119.4	C10—C14—H14B	109.5
C1—C6—H6A	119.4	H14C—C14—H14B	109.5
O1—C7—N1	122.88 (18)	C10—C14—H14A	109.5
O1—C7—C1	120.08 (17)	H14C—C14—H14A	109.5
N1—C7—C1	117.03 (16)	H14B—C14—H14A	109.5
C13—C8—C9	120.2 (2)	C7—N1—C8	127.20 (16)
C13—C8—N1	116.8 (2)	C7—N1—H1A	116.4
C9—C8—N1	123.0 (2)	C8—N1—H1A	116.4

C6—C1—C2—C3	0.4 (3)	C13—C8—C9—C10	1.3 (3)
C7—C1—C2—C3	−177.07 (19)	N1—C8—C9—C10	179.60 (17)
C1—C2—C3—C4	1.3 (4)	C8—C9—C10—C11	0.4 (3)
C2—C3—C4—C5	−2.2 (4)	C8—C9—C10—C14	−179.9 (2)
C2—C3—C4—Cl1	176.97 (18)	C9—C10—C11—C12	−1.7 (3)
C3—C4—C5—C6	1.3 (3)	C14—C10—C11—C12	178.6 (2)
Cl1—C4—C5—C6	−177.83 (15)	C10—C11—C12—C13	1.4 (4)
C4—C5—C6—C1	0.5 (3)	C9—C8—C13—C12	−1.6 (3)
C2—C1—C6—C5	−1.3 (3)	N1—C8—C13—C12	179.96 (18)
C7—C1—C6—C5	176.33 (17)	C11—C12—C13—C8	0.3 (3)
C2—C1—C7—O1	162.80 (19)	O1—C7—N1—C8	−4.9 (3)
C6—C1—C7—O1	−14.7 (3)	C1—C7—N1—C8	173.59 (17)
C2—C1—C7—N1	−15.7 (3)	C13—C8—N1—C7	−151.2 (2)
C6—C1—C7—N1	166.77 (17)	C9—C8—N1—C7	30.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	2.06	2.888 (2)	161

Symmetry code: (i) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂ClNO
M_r	245.70
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.4379 (9), 10.2493 (11), 9.2600 (7)
β (°)	92.893 (6)
V (Å³)	1273.74 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.81 × 0.17 × 0.04

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector
Absorption correction	Analytical [CrysAlis RED (Oxford Diffraction, 2009), based on expressions derived from Clark & Reid (1995)]
T_min, T_max	0.877, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	17187, 2156, 1299
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.588

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.117, 0.94
No. of reflections	2156
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.13

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008), enCIFer (Allen et al., 2004).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	2.06	2.888 (2)	161.2

Symmetry code: (i) x, −y+1/2, z+1/2.

Acknowledgements

MF 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 (Slovakia) APVV-0202–10 and the Structural Funds, Interreg IIIA, for financial support in purchasing the diffractometer. VZR thanks the University Grants Commission, Government of India, New Delhi, for the award of an RFSMS research fellowship.

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