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

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.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.037
• wR factor = 0.101
• Data-to-parameter ratio = 7.4

checkCIF/PLATON results

No syntax errors found



Alert level C
CELLV02_ALERT_1_C  The supplied cell volume s.u. differs from that
            calculated from the cell parameter s.u.'s by > 2
            Calculated cell volume su =       5.11
            Cell volume su given      =       3.00
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.39
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C9
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           66.76
           From the CIF: _reflns_number_total               1168
           Count of symmetry unique reflns         1168
           Completeness (_total/calc)            100.00%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

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

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

S2. Experimental

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.

S3. Refinement

The NH atom was located in difference map and was refined with restrained geometry, viz. N—H distance was restrained to 0.86 (2) Å. The other H atoms were positioned with idealized geometry using a riding model with C—H = 0.93–0.96 Å A l l H atoms were refined with isotropic displacement parameters (set to 1.2 times of the U_eq of the parent atom).

In the absence of significant anomalous dispersion effects, Friedel pairs were merged and the Δf"term set to zero.

Computing details

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

	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

Crystal data

C15H15NO	Dx = 1.186 Mg m^−3
Mr = 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) Å^3	Prism, colourless
Z = 4	0.55 × 0.30 × 0.30 mm
F(000) = 480

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.016
Radiation source: fine-focus sealed tube	θmax = 66.8°, θmin = 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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.100	w = 1/[σ^2(Fo^2) + (0.0637P)^2 + 0.0805P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
1168 reflections	Δρmax = 0.12 e Å^−3
158 parameters	Δρmin = −0.10 e Å^−3
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0069 (14)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.84 (2)	2.10 (2)	2.908 (3)	163 (3)

Symmetry code: (i) −y+1, x, z−1/4.