N-(3-Chloro­phen­yl)-2-methyl­benzamide

Gowda, B.T.; Foro, S.; Sowmya, B.P.; Fuess, H.

doi:10.1107/S1600536808010143

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o861

doi:10.1107/S1600536808010143

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N-(3-Chlorophenyl)-2-methylbenzamide

B. Thimme Gowda,^a ^* Sabine Foro,^b B. P. Sowmya ^a and Hartmut Fuess ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 8 April 2008; accepted 14 April 2008; online 16 April 2008)

The conformation of the N—H bond in the structure of the title compound, C₁₄H₁₂ClNO, is anti to the meta-chloro substituent in the aniline ring, while the C=O bond is syn to the ortho-methyl substituent in the benzoyl ring. The conformations of the N—H and C=O bonds are anti to each other, similar to those observed in 2-methyl-N-(3-methylphenyl)benzamide (N3MP2MBA). The –NHC(=O)– group makes a dihedral angle of 55.8 (7)° with the benzoyl ring, while the angle between the benzoyl and aniline rings is 37.5 (1)°; the respective values for N3MP2MBA are 55.2 (7) and 36.2 (1)°. N—H⋯O hydrogen bonds link the molecules into infinite chains running along the c axis.

Related literature

For related literature, see: Gowda et al. (2003 , 2008a ,b ).

Experimental

Crystal data

C₁₄H₁₂ClNO
M_r = 245.70
Tetragonal, P 4₃
a = 8.8237 (8) Å
c = 15.977 (2) Å
V = 1243.9 (2) Å³
Z = 4
Cu Kα radiation
μ = 2.57 mm⁻¹
T = 299 (2) K
0.60 × 0.10 × 0.07 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.308, T_max = 0.841
4144 measured reflections
2173 independent reflections
1844 reflections with I > 2σ(I)
R_int = 0.036
3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.120
S = 1.07
2173 reflections
159 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.29 e Å⁻³
Absolute structure: Flack (1983 ), 1020 Friedel pairs
Flack parameter: 0.00 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.83 (4)	2.12 (4)	2.900 (3)	157 (3)
Symmetry code: (i) $[-y+1, x, z-{\script{1\over 4}}]$ .

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808010143/om2228sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808010143/om2228Isup2.hkl

checkCIF report

Comment top

In the present work, the structure of 2-methyl-N-(3-chlorophenyl)- benzamide (N3CP2MBA) has been determined as part of substituent effect studies on the solid state structures of benzanilides (Gowda et al., 2003; Gowda et al. (2008a, 2008b). The conformation of the N—H bond in N3CP2MBA (Fig. 1) is anti to the meta-chloro substituent in the aniline ring, while the C=O bond is syn to the ortho-methyl substituent in the benzoyl ring and the conformations of the N—H and C=O bonds are anti to each other, identical to that observed in 2-methyl-N-(3-methylphenyl)-benzamide (N3MP2MBA). The bond parameters in N3CP2MBA are similar to those in 2-methyl-N-(phenyl)-benzamide (Gowda et al., 2008a), N3MP2MBA (Gowda et al., 2008b) and other benzanilides (Gowda et al., 2003). The amide group, –NHCO– makes a dihedral angle of 55.8 (7)° with the benzoyl ring, while that between benzoyl and aniline rings is 37.5 (1)°, compared to the respective values of 55.2 (7)° and 36.2 (1)° for N3MP2MBA. The packing diagram of N3CP2MBA showing the hydrogen bonds N1—H1N···O1 (Table 1) is given in Fig. 2.

Related literature top

For related literature, see: Gowda et al. (2003, 2008a,b).

Experimental top

The title compound was prepared according to the literature method (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. Single crystals of the title compound were obtained from an ethanolic solution and used for X-ray diffraction studies at room temperature.

Computing details top

Data collection: CAD-4-PC (Enraf–Nonius, 1996); cell refinement: CAD-4-PC (Enraf–Nonius, 1996); data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom labeling. Displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Molecular packing of the title compound as viewed down a and with hydrogen bonding shown as dashed lines.

N-(3-Chlorophenyl)-2-methylbenzamide top

Crystal data top

C₁₄H₁₂ClNO	D_x = 1.312 Mg m⁻³
M_r = 245.70	Cu Kα radiation, λ = 1.54180 Å
Tetragonal, P4₃	Cell parameters from 25 reflections
Hall symbol: P 4cw	θ = 5.7–21.9°
a = 8.8237 (8) Å	µ = 2.57 mm⁻¹
c = 15.977 (2) Å	T = 299 K
V = 1243.9 (2) Å³	Rod, colourless
Z = 4	0.60 × 0.10 × 0.07 mm
F(000) = 512

Data collection top

Enraf–Nonius CAD-4 diffractometer	1844 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.036
Graphite monochromator	θ_max = 66.9°, θ_min = 5.0°
ω/2θ scans	h = −10→10
Absorption correction: psi-scan (North et al., 1968)	k = −10→1
T_min = 0.308, T_max = 0.841	l = −19→16
4144 measured reflections	3 standard reflections every 120 min
2173 independent reflections	intensity decay: none

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.042	w = 1/[σ²(F_o²) + (0.0774P)² + 0.019P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.120	(Δ/σ)_max = 0.025
S = 1.07	Δρ_max = 0.19 e Å⁻³
2173 reflections	Δρ_min = −0.29 e Å⁻³
159 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0079 (12)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1020 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.00 (2)

Crystal data top

C₁₄H₁₂ClNO	Z = 4
M_r = 245.70	Cu Kα radiation
Tetragonal, P4₃	µ = 2.57 mm⁻¹
a = 8.8237 (8) Å	T = 299 K
c = 15.977 (2) Å	0.60 × 0.10 × 0.07 mm
V = 1243.9 (2) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	1844 reflections with I > 2σ(I)
Absorption correction: psi-scan (North et al., 1968)	R_int = 0.036
T_min = 0.308, T_max = 0.841	3 standard reflections every 120 min
4144 measured reflections	intensity decay: none
2173 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.120	Δρ_max = 0.19 e Å⁻³
S = 1.07	Δρ_min = −0.29 e Å⁻³
2173 reflections	Absolute structure: Flack (1983), 1020 Friedel pairs
159 parameters	Absolute structure parameter: 0.00 (2)
1 restraint

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	0.6762 (3)	0.7532 (3)	0.05087 (15)	0.0463 (6)
C2	0.7849 (3)	0.7433 (3)	0.11372 (17)	0.0528 (6)
H2	0.8336	0.6521	0.1249	0.063*
C3	0.8186 (4)	0.8716 (4)	0.15884 (17)	0.0627 (8)
C4	0.7505 (5)	1.0087 (4)	0.1436 (2)	0.0763 (10)
H4	0.7762	1.0940	0.1747	0.092*
C5	0.6440 (5)	1.0169 (4)	0.0815 (2)	0.0831 (11)
H5	0.5963	1.1088	0.0705	0.100*
C6	0.6061 (4)	0.8896 (3)	0.0346 (2)	0.0673 (8)
H6	0.5337	0.8965	−0.0075	0.081*
C7	0.6591 (3)	0.4810 (3)	0.01510 (14)	0.0452 (5)
C8	0.5994 (3)	0.3752 (3)	−0.05047 (17)	0.0516 (6)
C9	0.6935 (4)	0.2659 (3)	−0.08605 (18)	0.0644 (8)
C10	0.6279 (6)	0.1643 (4)	−0.1412 (2)	0.0887 (12)
H10	0.6885	0.0897	−0.1650	0.106*
C11	0.4808 (7)	0.1690 (4)	−0.1617 (3)	0.0992 (14)
H11	0.4415	0.0984	−0.1991	0.119*
C12	0.3864 (5)	0.2793 (5)	−0.1272 (3)	0.0955 (13)
H12	0.2841	0.2826	−0.1411	0.115*
C13	0.4472 (4)	0.3834 (4)	−0.0721 (2)	0.0695 (8)
H13	0.3863	0.4591	−0.0495	0.083*
C14	0.8575 (5)	0.2539 (5)	−0.0653 (3)	0.0923 (12)
H14A	0.8693	0.2414	−0.0059	0.111*
H14B	0.9088	0.3444	−0.0828	0.111*
H14C	0.9003	0.1680	−0.0936	0.111*
N1	0.6388 (3)	0.6279 (2)	−0.00053 (14)	0.0488 (5)
H1N	0.594 (4)	0.650 (3)	−0.045 (2)	0.059*
O1	0.7197 (2)	0.4315 (2)	0.07953 (11)	0.0598 (5)
Cl1	0.95205 (13)	0.85850 (13)	0.23813 (6)	0.0996 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0581 (14)	0.0483 (13)	0.0324 (12)	−0.0062 (11)	0.0045 (10)	0.0009 (10)
C2	0.0615 (15)	0.0546 (14)	0.0421 (13)	−0.0076 (11)	0.0013 (11)	0.0021 (11)
C3	0.0766 (18)	0.0721 (19)	0.0394 (15)	−0.0252 (15)	0.0044 (13)	−0.0071 (13)
C4	0.115 (3)	0.0605 (18)	0.0538 (19)	−0.0194 (18)	0.0127 (18)	−0.0145 (15)
C5	0.125 (3)	0.0505 (15)	0.074 (2)	0.0089 (18)	0.012 (2)	−0.0043 (16)
C6	0.092 (2)	0.0568 (16)	0.0532 (17)	0.0043 (14)	−0.0034 (16)	0.0023 (13)
C7	0.0528 (13)	0.0500 (13)	0.0327 (13)	−0.0022 (10)	0.0041 (10)	0.0020 (10)
C8	0.0721 (17)	0.0465 (13)	0.0361 (13)	−0.0069 (11)	−0.0036 (11)	0.0030 (10)
C9	0.094 (2)	0.0559 (15)	0.0434 (15)	0.0070 (15)	−0.0037 (14)	−0.0022 (12)
C10	0.149 (4)	0.0572 (18)	0.059 (2)	0.006 (2)	−0.020 (2)	−0.0159 (15)
C11	0.162 (4)	0.064 (2)	0.071 (2)	−0.034 (3)	−0.034 (3)	−0.0049 (18)
C12	0.103 (3)	0.095 (3)	0.089 (3)	−0.039 (2)	−0.039 (2)	0.009 (2)
C13	0.0712 (19)	0.0665 (17)	0.071 (2)	−0.0106 (15)	−0.0094 (15)	0.0044 (15)
C14	0.099 (3)	0.109 (3)	0.069 (2)	0.035 (2)	0.0100 (19)	−0.012 (2)
N1	0.0627 (13)	0.0512 (11)	0.0324 (10)	0.0005 (9)	−0.0063 (10)	0.0014 (9)
O1	0.0893 (13)	0.0559 (10)	0.0342 (10)	0.0054 (9)	−0.0073 (9)	0.0033 (8)
Cl1	0.1114 (7)	0.1195 (8)	0.0678 (6)	−0.0442 (6)	−0.0276 (5)	−0.0081 (5)

Geometric parameters (Å, º) top

C1—C6	1.377 (4)	C8—C13	1.388 (4)
C1—C2	1.391 (4)	C8—C9	1.394 (4)
C1—N1	1.416 (3)	C9—C10	1.384 (5)
C2—C3	1.374 (4)	C9—C14	1.488 (5)
C2—H2	0.9300	C10—C11	1.339 (7)
C3—C4	1.373 (5)	C10—H10	0.9300
C3—Cl1	1.734 (3)	C11—C12	1.394 (7)
C4—C5	1.368 (6)	C11—H11	0.9300
C4—H4	0.9300	C12—C13	1.382 (5)
C5—C6	1.392 (5)	C12—H12	0.9300
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	C14—H14A	0.9600
C7—O1	1.240 (3)	C14—H14B	0.9600
C7—N1	1.332 (3)	C14—H14C	0.9600
C7—C8	1.499 (3)	N1—H1N	0.83 (4)

C6—C1—C2	120.0 (2)	C10—C9—C8	117.3 (3)
C6—C1—N1	117.9 (2)	C10—C9—C14	120.2 (3)
C2—C1—N1	122.0 (2)	C8—C9—C14	122.5 (3)
C3—C2—C1	118.4 (3)	C11—C10—C9	122.8 (4)
C3—C2—H2	120.8	C11—C10—H10	118.6
C1—C2—H2	120.8	C9—C10—H10	118.6
C4—C3—C2	122.6 (3)	C10—C11—C12	120.3 (3)
C4—C3—Cl1	119.1 (2)	C10—C11—H11	119.9
C2—C3—Cl1	118.4 (3)	C12—C11—H11	119.9
C5—C4—C3	118.4 (3)	C13—C12—C11	118.9 (4)
C5—C4—H4	120.8	C13—C12—H12	120.5
C3—C4—H4	120.8	C11—C12—H12	120.5
C4—C5—C6	120.8 (3)	C12—C13—C8	120.0 (4)
C4—C5—H5	119.6	C12—C13—H13	120.0
C6—C5—H5	119.6	C8—C13—H13	120.0
C1—C6—C5	119.7 (3)	C9—C14—H14A	109.5
C1—C6—H6	120.1	C9—C14—H14B	109.5
C5—C6—H6	120.1	H14A—C14—H14B	109.5
O1—C7—N1	123.8 (2)	C9—C14—H14C	109.5
O1—C7—C8	120.8 (2)	H14A—C14—H14C	109.5
N1—C7—C8	115.3 (2)	H14B—C14—H14C	109.5
C13—C8—C9	120.7 (3)	C7—N1—C1	128.3 (2)
C13—C8—C7	118.8 (3)	C7—N1—H1N	117 (2)
C9—C8—C7	120.5 (3)	C1—N1—H1N	115 (2)

C6—C1—C2—C3	0.5 (4)	C7—C8—C9—C10	174.9 (3)
N1—C1—C2—C3	177.7 (2)	C13—C8—C9—C14	179.4 (3)
C1—C2—C3—C4	−0.8 (4)	C7—C8—C9—C14	−3.6 (4)
C1—C2—C3—Cl1	179.1 (2)	C8—C9—C10—C11	0.9 (5)
C2—C3—C4—C5	0.7 (5)	C14—C9—C10—C11	179.5 (4)
Cl1—C3—C4—C5	−179.2 (3)	C9—C10—C11—C12	0.0 (6)
C3—C4—C5—C6	−0.4 (5)	C10—C11—C12—C13	0.3 (6)
C2—C1—C6—C5	−0.3 (5)	C11—C12—C13—C8	−1.4 (6)
N1—C1—C6—C5	−177.5 (3)	C9—C8—C13—C12	2.3 (5)
C4—C5—C6—C1	0.2 (6)	C7—C8—C13—C12	−174.7 (3)
O1—C7—C8—C13	121.7 (3)	O1—C7—N1—C1	−1.7 (4)
N1—C7—C8—C13	−56.8 (3)	C8—C7—N1—C1	176.9 (2)
O1—C7—C8—C9	−55.2 (3)	C6—C1—N1—C7	−160.9 (3)
N1—C7—C8—C9	126.2 (3)	C2—C1—N1—C7	21.9 (4)
C13—C8—C9—C10	−2.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.83 (4)	2.12 (4)	2.900 (3)	157 (3)

Symmetry code: (i) −y+1, x, z−1/4.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₂ClNO
M_r	245.70
Crystal system, space group	Tetragonal, P4₃
Temperature (K)	299
a, c (Å)	8.8237 (8), 15.977 (2)
V (Å³)	1243.9 (2)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	2.57
Crystal size (mm)	0.60 × 0.10 × 0.07

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	Psi-scan (North et al., 1968)
T_min, T_max	0.308, 0.841
No. of measured, independent and observed [I > 2σ(I)] reflections	4144, 2173, 1844
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.120, 1.07
No. of reflections	2173
No. of parameters	159
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)	0.19, −0.29
Absolute structure	Flack (1983), 1020 Friedel pairs
Absolute structure parameter	0.00 (2)

Computer programs: CAD-4-PC (Enraf–Nonius, 1996), REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.83 (4)	2.12 (4)	2.900 (3)	157 (3)

Symmetry code: (i) −y+1, x, z−1/4.

Acknowledgements

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.

References

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