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

The mol-ecular structure of the title compound, C(15)H(15)NO, involves an intra-molecular C-H⋯O hydrogen bond. The central amide group -NH-C(=O)- is twisted by 37.95 (12)° out of the meta-substituted benzoyl ring and by 37.88 (12)° out of the ortho-substituted aniline ring. The two benzene rings are inclined to one another at only 4.2 (1)° having an inter-planar spacing of ca 0.90 Å. The crystal structure is stabilized by inter-molecular N-H⋯O hydrogen bonds, which link the mol-ecules into chains running along the b axis. A weak inter-molecular C-H⋯π inter-action is also present.

Related literature

For the preparation of the title compound, see: Gowda et al. (2003 ▶). For related structures, see: Bowes et al. (2003 ▶); Gowda et al. (2008 ▶); Rodrigues et al. (2010 ▶).

Experimental

Crystal data

C15H15NO

M = 225.28

Monoclinic,

a = 11.1896 (3) Å

b = 4.95027 (14) Å

c = 24.1164 (5) Å

β = 116.512 (2)°

V = 1195.37 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.55 × 0.13 × 0.08 mm

Data collection

Oxford Diffraction Gemini R CCD diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.954, T max = 0.993

13694 measured reflections

2124 independent reflections

1553 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.126

S = 1.02

2124 reflections

156 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2002 ▶); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810024578/vm2033sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024578/vm2033Isup2.hkl

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

C15H15NO	F(000) = 480
Mr = 225.28	Dx = 1.252 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6151 reflections
a = 11.1896 (3) Å	θ = 3.4–29.4°
b = 4.95027 (14) Å	µ = 0.08 mm−1
c = 24.1164 (5) Å	T = 295 K
β = 116.512 (2)°	Rod, colorless
V = 1195.37 (5) Å3	0.55 × 0.13 × 0.08 mm
Z = 4

Oxford Diffraction Gemini R CCD diffractometer	2124 independent reflections
graphite	1553 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1	Rint = 0.036
ω scans	θmax = 25.1°, θmin = 2.1°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −13→13
Tmin = 0.954, Tmax = 0.993	k = −5→5
13694 measured reflections	l = −28→28

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.085P)2] where P = (Fo2 + 2Fc2)/3
2124 reflections	(Δ/σ)max < 0.001
156 parameters	Δρmax = 0.18 e Å−3
1 restraint	Δρmin = −0.16 e Å−3

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	0.60977 (14)	0.5878 (3)	0.45102 (7)	0.0380 (4)
C2	0.62846 (15)	0.3929 (3)	0.41406 (7)	0.0400 (4)
H2	0.7127	0.3169	0.4269	0.048*
C3	0.52474 (15)	0.3091 (3)	0.35868 (7)	0.0421 (4)
C4	0.40013 (16)	0.4216 (3)	0.34128 (8)	0.0485 (4)
H4	0.3288	0.3659	0.3046	0.058*
C5	0.37946 (16)	0.6155 (3)	0.37739 (8)	0.0496 (4)
H5	0.2947	0.6884	0.3649	0.06*
C6	0.48384 (15)	0.7010 (3)	0.43174 (7)	0.0445 (4)
H6	0.4701	0.8342	0.4555	0.053*
C7	0.72176 (14)	0.6863 (3)	0.50986 (7)	0.0386 (4)
C8	0.92671 (14)	0.5441 (3)	0.60094 (7)	0.0366 (4)
C9	1.04382 (15)	0.4018 (3)	0.61249 (7)	0.0398 (4)
C10	1.15481 (17)	0.4475 (3)	0.66806 (8)	0.0529 (5)
H10	1.233	0.353	0.6767	0.064*
C11	1.15358 (18)	0.6281 (4)	0.71109 (8)	0.0587 (5)
H11	1.2302	0.6558	0.748	0.07*
C12	1.03848 (18)	0.7672 (3)	0.69924 (8)	0.0543 (5)
H12	1.0372	0.89	0.7282	0.065*
C13	0.92508 (16)	0.7255 (3)	0.64467 (7)	0.0453 (4)
H13	0.8471	0.8189	0.637	0.054*
C14	0.54820 (18)	0.1002 (3)	0.31908 (8)	0.0551 (5)
H14A	0.6314	0.1368	0.318	0.083*
H14B	0.4767	0.107	0.2778	0.083*
H14C	0.5514	−0.0761	0.3363	0.083*
C15	1.04971 (16)	0.2057 (3)	0.56617 (8)	0.0499 (4)
H15A	1.0146	0.2898	0.5261	0.075*
H15B	0.9975	0.0487	0.5641	0.075*
H15C	1.1407	0.1533	0.5787	0.075*
N1	0.81081 (12)	0.4968 (2)	0.54447 (6)	0.0394 (3)
H1N	0.796	0.3332	0.5311	0.047*
O1	0.73096 (11)	0.92511 (18)	0.52470 (5)	0.0555 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0434 (9)	0.0277 (7)	0.0421 (9)	0.0000 (6)	0.0184 (7)	0.0039 (6)
C2	0.0405 (9)	0.0322 (8)	0.0451 (9)	0.0024 (6)	0.0172 (8)	0.0041 (6)
C3	0.0503 (10)	0.0331 (8)	0.0414 (9)	−0.0044 (7)	0.0190 (8)	0.0033 (7)
C4	0.0452 (10)	0.0472 (9)	0.0439 (10)	−0.0068 (7)	0.0116 (8)	0.0023 (7)
C5	0.0404 (9)	0.0523 (10)	0.0530 (10)	0.0054 (7)	0.0180 (8)	0.0063 (8)
C6	0.0477 (10)	0.0391 (8)	0.0476 (9)	0.0036 (7)	0.0222 (8)	0.0013 (7)
C7	0.0415 (9)	0.0288 (8)	0.0462 (9)	−0.0012 (6)	0.0202 (7)	0.0015 (6)
C8	0.0420 (9)	0.0272 (7)	0.0388 (8)	−0.0049 (6)	0.0164 (7)	−0.0007 (6)
C9	0.0437 (9)	0.0309 (8)	0.0450 (9)	−0.0030 (6)	0.0199 (8)	−0.0003 (6)
C10	0.0439 (9)	0.0513 (10)	0.0548 (11)	0.0004 (7)	0.0141 (8)	−0.0028 (8)
C11	0.0535 (11)	0.0618 (11)	0.0454 (10)	−0.0098 (9)	0.0084 (9)	−0.0104 (9)
C12	0.0686 (12)	0.0491 (10)	0.0450 (10)	−0.0097 (8)	0.0252 (9)	−0.0135 (8)
C13	0.0505 (10)	0.0387 (8)	0.0486 (10)	−0.0018 (7)	0.0237 (8)	−0.0057 (7)
C14	0.0655 (12)	0.0476 (10)	0.0492 (10)	−0.0023 (8)	0.0228 (9)	−0.0065 (8)
C15	0.0497 (10)	0.0452 (9)	0.0545 (10)	0.0031 (7)	0.0230 (8)	−0.0056 (8)
N1	0.0435 (8)	0.0259 (6)	0.0423 (7)	−0.0005 (5)	0.0134 (6)	−0.0039 (5)
O1	0.0611 (8)	0.0243 (6)	0.0653 (8)	0.0002 (5)	0.0141 (6)	−0.0038 (5)

C1—C6	1.390 (2)	C9—C10	1.380 (2)
C1—C2	1.391 (2)	C9—C15	1.504 (2)
C1—C7	1.495 (2)	C10—C11	1.374 (2)
C2—C3	1.385 (2)	C10—H10	0.93
C2—H2	0.93	C11—C12	1.373 (2)
C3—C4	1.381 (2)	C11—H11	0.93
C3—C14	1.508 (2)	C12—C13	1.376 (2)
C4—C5	1.383 (2)	C12—H12	0.93
C4—H4	0.93	C13—H13	0.93
C5—C6	1.376 (2)	C14—H14A	0.96
C5—H5	0.93	C14—H14B	0.96
C6—H6	0.93	C14—H14C	0.96
C7—O1	1.2262 (16)	C15—H15A	0.96
C7—N1	1.3517 (18)	C15—H15B	0.96
C8—C13	1.391 (2)	C15—H15C	0.96
C8—C9	1.402 (2)	N1—H1N	0.86
C8—N1	1.4194 (19)
C6—C1—C2	119.03 (14)	C11—C10—C9	122.13 (16)
C6—C1—C7	118.77 (13)	C11—C10—H10	118.9
C2—C1—C7	122.16 (13)	C9—C10—H10	118.9
C3—C2—C1	121.63 (14)	C12—C11—C10	119.58 (16)
C3—C2—H2	119.2	C12—C11—H11	120.2
C1—C2—H2	119.2	C10—C11—H11	120.2
C4—C3—C2	118.03 (14)	C11—C12—C13	120.16 (15)
C4—C3—C14	121.44 (14)	C11—C12—H12	119.9
C2—C3—C14	120.54 (14)	C13—C12—H12	119.9
C3—C4—C5	121.22 (15)	C12—C13—C8	120.21 (15)
C3—C4—H4	119.4	C12—C13—H13	119.9
C5—C4—H4	119.4	C8—C13—H13	119.9
C6—C5—C4	120.25 (15)	C3—C14—H14A	109.5
C6—C5—H5	119.9	C3—C14—H14B	109.5
C4—C5—H5	119.9	H14A—C14—H14B	109.5
C5—C6—C1	119.82 (15)	C3—C14—H14C	109.5
C5—C6—H6	120.1	H14A—C14—H14C	109.5
C1—C6—H6	120.1	H14B—C14—H14C	109.5
O1—C7—N1	123.11 (14)	C9—C15—H15A	109.5
O1—C7—C1	121.14 (13)	C9—C15—H15B	109.5
N1—C7—C1	115.75 (12)	H15A—C15—H15B	109.5
C13—C8—C9	120.07 (14)	C9—C15—H15C	109.5
C13—C8—N1	121.22 (13)	H15A—C15—H15C	109.5
C9—C8—N1	118.71 (13)	H15B—C15—H15C	109.5
C10—C9—C8	117.84 (14)	C7—N1—C8	125.73 (12)
C10—C9—C15	120.56 (14)	C7—N1—H1N	117.1
C8—C9—C15	121.60 (14)	C8—N1—H1N	117.1
C6—C1—C2—C3	0.0 (2)	N1—C8—C9—C10	−179.00 (13)
C7—C1—C2—C3	−178.03 (13)	C13—C8—C9—C15	−179.54 (14)
C1—C2—C3—C4	−1.1 (2)	N1—C8—C9—C15	1.1 (2)
C1—C2—C3—C14	179.15 (13)	C8—C9—C10—C11	−0.8 (2)
C2—C3—C4—C5	1.1 (2)	C15—C9—C10—C11	179.06 (15)
C14—C3—C4—C5	−179.21 (15)	C9—C10—C11—C12	0.6 (3)
C3—C4—C5—C6	0.2 (2)	C10—C11—C12—C13	0.1 (3)
C4—C5—C6—C1	−1.4 (2)	C11—C12—C13—C8	−0.6 (2)
C2—C1—C6—C5	1.3 (2)	C9—C8—C13—C12	0.4 (2)
C7—C1—C6—C5	179.36 (14)	N1—C8—C13—C12	179.69 (14)
C6—C1—C7—O1	−36.9 (2)	O1—C7—N1—C8	−1.3 (2)
C2—C1—C7—O1	141.04 (15)	C1—C7—N1—C8	178.10 (13)
C6—C1—C7—N1	143.59 (14)	C13—C8—N1—C7	39.2 (2)
C2—C1—C7—N1	−38.4 (2)	C9—C8—N1—C7	−141.47 (15)
C13—C8—C9—C10	0.4 (2)

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.86	2.13	2.9417 (14)	157
C13—H13···O1	0.93	2.48	2.908 (2)	108
C14—H14c···Cg1i	0.96	2.70	3.627 (2)	161

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.86	2.13	2.9417 (14)	157
C13—H13⋯O1	0.93	2.48	2.908 (2)	108
C14—H14c⋯Cg1i	0.96	2.70	3.627 (2)	161

Symmetry code: (i) .