2-Methyl-N-(3-methyl­phen­yl)benzamide

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

doi:10.1107/S1600536808003103

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o541

doi:10.1107/S1600536808003103

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2-Methyl-N-(3-methylphenyl)benzamide

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 18 January 2008; accepted 28 January 2008; online 30 January 2008)

In the structure of the title compound (N3MP2MBA), C₁₅H₁₅NO, the conformation of the N—H bond is anti to the meta-methyl substituent in the aniline ring and that of the C=O bond is syn to the ortho-methyl substituent in the benzoyl ring, while the conformations of the N—H and C=O bonds are anti to each other. The bond parameters in N3MP2MBA are similar to those in 2-methyl-N-phenylbenzamide, N-(3,4-dimethylphenyl)benzamide and other benzanilides. The amide group, –NHCO–, makes a dihedral angle of 55.2 (7)° with the benzoyl ring, while the dihedral angle between the two benzene rings (benzoyl and aniline) is 36.2 (1)°. N—H⋯O hydrogen bonds give rise to infinite chains running along the b axis of the crystal structure.

Related literature

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

Experimental

Crystal data

C₁₅H₁₅NO
M_r = 225.28
Tetragonal, P 4₃
a = 8.931 (2) Å
c = 15.816 (4) Å
V = 1261.5 (3) Å³
Z = 4
Cu Kα radiation
μ = 0.58 mm⁻¹
T = 299 (2) K
0.55 × 0.30 × 0.30 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
1606 measured reflections
1168 independent reflections
1096 reflections with I > 2σ(I)
R_int = 0.016
3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.100
S = 1.07
1168 reflections
158 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.10 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.837 (18)	2.10 (2)	2.908 (3)	163 (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/S1600536808003103/om2212sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808003103/om2212Isup2.hkl

checkCIF report

Comment top

As part of a study of the substituent effects on the structures of N-aromatic amides, in the present work, the structure of N-(3-methylphenyl)-2-methylbenzamide (N3MP2MBA) has been determined (Gowda et al., 2003; 2008a; 2008b). In the structure of N3MP2MBA (Fig. 1), the conformation of the N—H bond is anti to the meta-methyl substituent in the aniline ring and that of the C=O bond is syn to the ortho-methyl substituent in the benzoyl ring, while the conformations of the N—H and C=O bonds are anti to each other. The bond parameters in N2MP2MBA are similar to those in N-(phenyl)-2-methylbenzamide (Gowda et al., 2008a), N-(3,4-dimethylphenyl)-benzamide (Gowda et al., 2008b) and other benzanilides (Gowda et al., 2003). The amide group –NHCO– has the dihedral angle of 55.2 (7)° with the benzoyl ring, while the dihedral angle between the two benzene rings (benzoyl and aniline) is 36.2 (1)°. The packing diagram of N3MP2MBA molecules showing the hydrogen bonds N1—H1N···O1 (Table 1) involved in the formation of molecular chain 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 Version (Enraf–Nonius, 1996); cell refinement: CAD-4-PC Version (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 scheme. The displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.

2-Methyl-N-(3-methylphenyl)benzamide top

Crystal data top

C₁₅H₁₅NO	D_x = 1.186 Mg m⁻³
M_r = 225.28	Cu Kα radiation, λ = 1.54180 Å
Tetragonal, P4₃	Cell parameters from 25 reflections
Hall symbol: P 4cw	θ = 4.9–19.0°
a = 8.931 (2) Å	µ = 0.58 mm⁻¹
c = 15.816 (4) Å	T = 299 K
V = 1261.5 (3) Å³	Prism, colourless
Z = 4	0.55 × 0.30 × 0.30 mm
F(000) = 480

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.016
Radiation source: fine-focus sealed tube	θ_max = 66.8°, θ_min = 5.0°
Graphite monochromator	h = −10→0
ω/2θ scans	k = −10→0
1606 measured reflections	l = −18→3
1168 independent reflections	3 standard reflections every 120 min
1096 reflections with I > 2σ(I)	intensity decay: 1.0%

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)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.100	w = 1/[σ²(F_o²) + (0.0637P)² + 0.0805P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
1168 reflections	Δρ_max = 0.12 e Å⁻³
158 parameters	Δρ_min = −0.10 e Å⁻³
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0069 (14)

Crystal data top

C₁₅H₁₅NO	Z = 4
M_r = 225.28	Cu Kα radiation
Tetragonal, P4₃	µ = 0.58 mm⁻¹
a = 8.931 (2) Å	T = 299 K
c = 15.816 (4) Å	0.55 × 0.30 × 0.30 mm
V = 1261.5 (3) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.016
1606 measured reflections	3 standard reflections every 120 min
1168 independent reflections	intensity decay: 1.0%
1096 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.036	2 restraints
wR(F²) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.12 e Å⁻³
1168 reflections	Δρ_min = −0.10 e Å⁻³
158 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	0.3124 (3)	0.2503 (2)	0.05561 (14)	0.0534 (5)
C2	0.2079 (3)	0.2607 (3)	0.12012 (15)	0.0601 (6)
H2	0.1629	0.3523	0.1317	0.072*
C3	0.1696 (3)	0.1353 (3)	0.16775 (15)	0.0681 (7)
C4	0.2385 (4)	0.0013 (3)	0.1499 (2)	0.0827 (9)
H4	0.2142	−0.0833	0.1813	0.099*
C5	0.3424 (4)	−0.0095 (3)	0.0865 (2)	0.0874 (9)
H5	0.3877	−0.1011	0.0752	0.105*
C6	0.3802 (3)	0.1149 (3)	0.03921 (17)	0.0718 (7)
H6	0.4512	0.1072	−0.0036	0.086*
C7	0.3347 (2)	0.5195 (2)	0.01949 (14)	0.0521 (5)
C8	0.3969 (3)	0.6215 (3)	−0.04697 (15)	0.0576 (6)
C9	0.3085 (4)	0.7335 (3)	−0.08194 (17)	0.0729 (7)
C10	0.3766 (6)	0.8318 (4)	−0.1386 (2)	0.1034 (12)
H10	0.3200	0.9078	−0.1630	0.124*
C11	0.5257 (7)	0.8189 (4)	−0.1590 (3)	0.1172 (16)
H11A	0.5692	0.8874	−0.1958	0.141*
C12	0.6101 (5)	0.7064 (5)	−0.1257 (3)	0.1091 (13)
H12A	0.7102	0.6964	−0.1408	0.131*
C13	0.5459 (4)	0.6074 (3)	−0.0694 (2)	0.0774 (8)
H13	0.6033	0.5307	−0.0463	0.093*
C14	0.0560 (4)	0.1486 (5)	0.2363 (2)	0.0956 (10)
H14A	−0.0376	0.1807	0.2127	0.115*
H14B	0.0894	0.2206	0.2773	0.115*
H14C	0.0431	0.0531	0.2632	0.115*
C15	0.1464 (4)	0.7517 (5)	−0.0604 (3)	0.1053 (12)
H15A	0.1361	0.7678	−0.0007	0.126*
H15B	0.0928	0.6629	−0.0763	0.126*
H15C	0.1064	0.8361	−0.0904	0.126*
N1	0.3505 (2)	0.3731 (2)	0.00353 (13)	0.0561 (5)
H1N	0.392 (3)	0.350 (3)	−0.0422 (14)	0.067*
O1	0.2763 (2)	0.56893 (19)	0.08395 (11)	0.0681 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0613 (12)	0.0547 (12)	0.0444 (11)	−0.0074 (9)	−0.0062 (10)	−0.0018 (9)
C2	0.0662 (13)	0.0625 (13)	0.0515 (13)	−0.0094 (10)	−0.0007 (11)	0.0011 (11)
C3	0.0790 (16)	0.0749 (16)	0.0504 (14)	−0.0251 (13)	−0.0092 (12)	0.0083 (12)
C4	0.112 (2)	0.0683 (16)	0.0680 (17)	−0.0192 (15)	−0.0136 (17)	0.0189 (14)
C5	0.123 (2)	0.0562 (14)	0.083 (2)	0.0044 (15)	−0.007 (2)	0.0070 (15)
C6	0.0897 (18)	0.0639 (14)	0.0619 (16)	0.0042 (12)	0.0023 (14)	−0.0021 (12)
C7	0.0558 (11)	0.0558 (11)	0.0447 (11)	−0.0033 (9)	−0.0023 (9)	−0.0026 (9)
C8	0.0721 (14)	0.0517 (12)	0.0490 (12)	−0.0063 (10)	0.0031 (11)	−0.0049 (10)
C9	0.102 (2)	0.0610 (14)	0.0560 (15)	0.0059 (13)	−0.0007 (14)	0.0014 (12)
C10	0.173 (4)	0.0676 (17)	0.070 (2)	0.008 (2)	0.016 (2)	0.0166 (15)
C11	0.180 (4)	0.078 (2)	0.093 (3)	−0.043 (3)	0.047 (3)	0.003 (2)
C12	0.111 (3)	0.093 (2)	0.123 (3)	−0.033 (2)	0.047 (3)	−0.007 (2)
C13	0.0777 (17)	0.0716 (16)	0.0828 (19)	−0.0131 (13)	0.0141 (15)	−0.0023 (14)
C14	0.107 (2)	0.112 (2)	0.0678 (18)	−0.0414 (19)	0.0137 (18)	0.0095 (18)
C15	0.105 (3)	0.125 (3)	0.086 (2)	0.038 (2)	−0.011 (2)	0.012 (2)
N1	0.0679 (12)	0.0564 (10)	0.0440 (9)	−0.0042 (8)	0.0088 (9)	−0.0027 (8)
O1	0.0946 (12)	0.0628 (10)	0.0468 (9)	0.0015 (9)	0.0096 (9)	−0.0054 (8)

Geometric parameters (Å, º) top

C1—C6	1.377 (4)	C9—C10	1.394 (5)
C1—C2	1.386 (3)	C9—C15	1.496 (5)
C1—N1	1.414 (3)	C10—C11	1.375 (7)
C2—C3	1.392 (3)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.361 (7)
C3—C4	1.375 (5)	C11—H11A	0.9300
C3—C14	1.490 (5)	C12—C13	1.380 (5)
C4—C5	1.369 (5)	C12—H12A	0.9300
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.381 (4)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—H6	0.9300	C14—H14C	0.9600
C7—O1	1.227 (3)	C15—H15A	0.9600
C7—N1	1.339 (3)	C15—H15B	0.9600
C7—C8	1.498 (3)	C15—H15C	0.9600
C8—C13	1.382 (4)	N1—H1N	0.837 (18)
C8—C9	1.389 (4)

C6—C1—C2	119.6 (2)	C11—C10—C9	121.4 (4)
C6—C1—N1	117.8 (2)	C11—C10—H10	119.3
C2—C1—N1	122.6 (2)	C9—C10—H10	119.3
C1—C2—C3	120.6 (2)	C12—C11—C10	120.5 (3)
C1—C2—H2	119.7	C12—C11—H11A	119.8
C3—C2—H2	119.7	C10—C11—H11A	119.8
C4—C3—C2	118.6 (3)	C11—C12—C13	119.5 (4)
C4—C3—C14	121.6 (3)	C11—C12—H12A	120.2
C2—C3—C14	119.8 (3)	C13—C12—H12A	120.2
C5—C4—C3	121.0 (3)	C12—C13—C8	120.4 (3)
C5—C4—H4	119.5	C12—C13—H13	119.8
C3—C4—H4	119.5	C8—C13—H13	119.8
C4—C5—C6	120.4 (3)	C3—C14—H14A	109.5
C4—C5—H5	119.8	C3—C14—H14B	109.5
C6—C5—H5	119.8	H14A—C14—H14B	109.5
C1—C6—C5	119.8 (3)	C3—C14—H14C	109.5
C1—C6—H6	120.1	H14A—C14—H14C	109.5
C5—C6—H6	120.1	H14B—C14—H14C	109.5
O1—C7—N1	123.5 (2)	C9—C15—H15A	109.5
O1—C7—C8	121.5 (2)	C9—C15—H15B	109.5
N1—C7—C8	114.97 (19)	H15A—C15—H15B	109.5
C13—C8—C9	120.7 (3)	C9—C15—H15C	109.5
C13—C8—C7	118.8 (2)	H15A—C15—H15C	109.5
C9—C8—C7	120.4 (2)	H15B—C15—H15C	109.5
C8—C9—C10	117.5 (3)	C7—N1—C1	128.5 (2)
C8—C9—C15	122.5 (3)	C7—N1—H1N	117 (2)
C10—C9—C15	120.0 (3)	C1—N1—H1N	115 (2)

C6—C1—C2—C3	−0.7 (3)	C7—C8—C9—C10	175.1 (3)
N1—C1—C2—C3	177.5 (2)	C13—C8—C9—C15	179.2 (3)
C1—C2—C3—C4	0.5 (4)	C7—C8—C9—C15	−4.4 (4)
C1—C2—C3—C14	−179.5 (3)	C8—C9—C10—C11	−0.1 (5)
C2—C3—C4—C5	−0.2 (4)	C15—C9—C10—C11	179.4 (4)
C14—C3—C4—C5	179.8 (3)	C9—C10—C11—C12	1.7 (6)
C3—C4—C5—C6	0.1 (5)	C10—C11—C12—C13	−1.7 (7)
C2—C1—C6—C5	0.7 (4)	C11—C12—C13—C8	0.3 (6)
N1—C1—C6—C5	−177.7 (3)	C9—C8—C13—C12	1.3 (5)
C4—C5—C6—C1	−0.4 (5)	C7—C8—C13—C12	−175.2 (3)
O1—C7—C8—C13	122.6 (3)	O1—C7—N1—C1	−3.0 (4)
N1—C7—C8—C13	−56.2 (3)	C8—C7—N1—C1	175.7 (2)
O1—C7—C8—C9	−53.9 (3)	C6—C1—N1—C7	−159.7 (2)
N1—C7—C8—C9	127.4 (2)	C2—C1—N1—C7	22.0 (4)
C13—C8—C9—C10	−1.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.84 (2)	2.10 (2)	2.908 (3)	163 (3)

Symmetry code: (i) −y+1, x, z−1/4.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₅NO
M_r	225.28
Crystal system, space group	Tetragonal, P4₃
Temperature (K)	299
a, c (Å)	8.931 (2), 15.816 (4)
V (Å³)	1261.5 (3)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.58
Crystal size (mm)	0.55 × 0.30 × 0.30

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	1606, 1168, 1096
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.100, 1.07
No. of reflections	1168
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)	0.12, −0.10

Computer programs: CAD-4-PC Version (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	0.837 (18)	2.10 (2)	2.908 (3)	163 (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

Enraf–Nonius (1996). CAD-4-PC. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Gowda, B. T., Foro, S., Sowmya, B. P. & Fuess, H. (2008a). Acta Cryst. E64, o383. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Jyothi, K., Paulus, H. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 225–230. CAS Google Scholar
Gowda, B. T., Tokarčík, M., Kožíšek, J., Sowmya, B. P. & Fuess, H. (2008b). Acta Cryst. E64, o340. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (1987). REDU4. Stoe & Cie GmbH, Darmstadt, Germany. Google Scholar