2-Methyl-N-(3-methyl-phen-yl)benzamide.

In the structure of the title compound (N3MP2MBA), C(15)H(15)NO, 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-phenyl-benzamide, N-(3,4-dimethyl-phen-yl)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 = 225.28

Tetragonal,

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[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.100

S = 1.07

1168 reflections

158 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.12 e Å−3

Δρmin = −0.10 e Å−3

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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808003103/om2212sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H15NO	Z = 4
Mr = 225.28	F000 = 480
Tetragonal, P43	Dx = 1.186 Mg m−3
Hall symbol: P 4cw	Cu Kα radiation λ = 1.54180 Å
a = 8.931 (2) Å	Cell parameters from 25 reflections
b = 8.931 (2) Å	θ = 4.9–19.0º
c = 15.816 (4) Å	µ = 0.58 mm−1
α = 90º	T = 299 (2) K
β = 90º	Prism, colourless
γ = 90º	0.55 × 0.30 × 0.30 mm
V = 1261.5 (3) Å3

Enraf–Nonius CAD-4 diffractometer	Rint = 0.016
Radiation source: fine-focus sealed tube	θmax = 66.8º
Monochromator: graphite	θmin = 5.0º
T = 299(2) K	h = −10→0
ω/2θ scans	k = −10→0
Absorption correction: none	l = −18→3
1606 measured reflections	3 standard reflections
1168 independent reflections	every 120 min
1096 reflections with I > 2σ(I)	intensity decay: 1.0%

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(Fo2) + (0.0637P)2 + 0.0805P] where P = (Fo2 + 2Fc2)/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+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0069 (14)

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.

	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)

	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)

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)

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)

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) .