4-Methyl-N-(4-methyl-phen-yl)benzamide.

In the title compound, C(15)H(15)NO, the amide fragment has an anti conformation. The central amide group is tilted with respect to the benzoyl ring, forming a dihedral angle of 32.3 (5)°. The benzoyl and aniline rings make a dihedral angle of 59.6 (5)°. Mol-ecules are linked into infinite supra-molecular chains via N-H⋯O hydrogen bonds. The mol-ecule is disordered so that the aromatic rings are disposed across a twofold axis with equal occupancies.

Related literature

For background to our study of the substituent effects on the structures of benzanilides, see: Gowda et al. (2003 ▶). For related structures, see Gowda et al. (2008 ▶, 2009 ▶).

Experimental

Crystal data

C15H15NO

M = 225.28

Monoclinic,

a = 13.3236 (5) Å

b = 5.3591 (2) Å

c = 17.3525 (6) Å

β = 92.248 (3)°

V = 1238.06 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.26 × 0.25 × 0.07 mm

Data collection

Oxford Diffraction Xcalibur System diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.984, T max = 0.995

8166 measured reflections

1235 independent reflections

775 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.103

S = 0.99

1235 reflections

154 parameters

59 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.12 e Å−3

Δρmin = −0.12 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; 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/S1600536809006497/tk2377sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006497/tk2377Isup2.hkl

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

C15H15NO	F(000) = 480
Mr = 225.28	Dx = 1.209 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2932 reflections
a = 13.3236 (5) Å	θ = 3.2–29.2°
b = 5.3591 (2) Å	µ = 0.08 mm−1
c = 17.3525 (6) Å	T = 295 K
β = 92.248 (3)°	Plate, colorless
V = 1238.06 (8) Å3	0.26 × 0.25 × 0.07 mm
Z = 4

Oxford Diffraction Xcalibur System diffractometer	1235 independent reflections
graphite	775 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1	Rint = 0.029
ω scans with κ offsets	θmax = 26.2°, θmin = 3.8°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	h = −16→16
Tmin = 0.984, Tmax = 0.995	k = −6→6
8166 measured reflections	l = −21→21

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = [exp(0.90(sinθ/λ)2)]/[σ2(Fo2) + (0.068P)2] where P = 0.33333Fo2 + 0.66667Fc2
1235 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.12 e Å−3
59 restraints	Δρmin = −0.12 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	Occ. (<1)
O1	0.5	−0.0539 (2)	0.25	0.0805 (4)
C8	0.52889 (16)	0.1648 (5)	0.26154 (14)	0.0581 (6)	0.5
C9	0.6171 (5)	0.2387 (10)	0.3106 (4)	0.0555 (13)	0.5
C10	0.6994 (7)	0.0833 (15)	0.3106 (7)	0.0633 (14)	0.5
H10	0.6972	−0.0616	0.2811	0.076*	0.5
C11	0.7862 (10)	0.142 (3)	0.3548 (6)	0.0640 (17)	0.5
H11	0.8413	0.0354	0.3549	0.077*	0.5
C12	0.7905 (9)	0.361 (3)	0.3989 (11)	0.061 (2)	0.5
C13	0.7076 (9)	0.522 (3)	0.3987 (9)	0.085 (3)	0.5
H13	0.7087	0.6686	0.4272	0.102*	0.5
C14	0.6229 (6)	0.4507 (13)	0.3538 (6)	0.0705 (18)	0.5
H14	0.5671	0.555	0.3533	0.085*	0.5
C15	0.8883 (6)	0.3929 (11)	0.4511 (4)	0.0850 (19)	0.5
H15A	0.8777	0.5189	0.4893	0.127*	0.5
H15B	0.9428	0.4419	0.4198	0.127*	0.5
H15C	0.9044	0.2375	0.4762	0.127*	0.5
N1	0.47296 (14)	0.3550 (4)	0.23226 (11)	0.0625 (6)	0.5
H1N	0.5	0.495 (4)	0.25	0.075*
C1	0.3832 (5)	0.3400 (10)	0.1864 (4)	0.0567 (15)	0.5
C2	0.3155 (8)	0.1540 (16)	0.1904 (7)	0.0730 (18)	0.5
H2	0.3287	0.0205	0.2235	0.088*	0.5
C3	0.2279 (10)	0.157 (3)	0.1466 (8)	0.083 (3)	0.5
H3	0.1838	0.0245	0.1517	0.099*	0.5
C4	0.2007 (11)	0.343 (3)	0.0962 (12)	0.076 (3)	0.5
C5	0.2728 (8)	0.520 (3)	0.0939 (8)	0.081 (2)	0.5
H5	0.2613	0.6482	0.0586	0.097*	0.5
C6	0.3605 (6)	0.5322 (14)	0.1370 (6)	0.0728 (17)	0.5
H6	0.4035	0.6677	0.1329	0.087*	0.5
C7	0.1050 (8)	0.3838 (19)	0.0558 (5)	0.146 (4)	0.5
H7A	0.0578	0.2603	0.0714	0.219*	0.5
H7B	0.1134	0.3716	0.0012	0.219*	0.5
H7C	0.0805	0.547	0.068	0.219*	0.5

	U11	U22	U33	U12	U13	U23
O1	0.0817 (8)	0.0553 (7)	0.1022 (9)	0	−0.0262 (7)	0
C8	0.0577 (18)	0.0537 (13)	0.0624 (16)	−0.0023 (10)	−0.0047 (12)	−0.0014 (11)
C9	0.0529 (18)	0.053 (3)	0.0602 (18)	0.001 (2)	−0.0042 (13)	−0.004 (2)
C10	0.052 (2)	0.063 (4)	0.074 (2)	0.004 (2)	−0.0032 (17)	−0.016 (3)
C11	0.046 (3)	0.078 (4)	0.067 (3)	0.003 (3)	−0.0077 (19)	−0.001 (2)
C12	0.045 (3)	0.077 (4)	0.058 (4)	−0.005 (2)	−0.016 (2)	0.000 (3)
C13	0.087 (5)	0.082 (4)	0.084 (4)	0.024 (4)	−0.023 (3)	−0.008 (3)
C14	0.056 (2)	0.070 (5)	0.084 (4)	0.011 (3)	−0.019 (2)	−0.004 (4)
C15	0.052 (2)	0.104 (3)	0.097 (5)	−0.017 (2)	−0.021 (2)	0.001 (3)
N1	0.0602 (15)	0.0521 (11)	0.0736 (15)	−0.0012 (9)	−0.0166 (9)	−0.0010 (9)
C1	0.0564 (17)	0.057 (4)	0.056 (2)	0.004 (3)	−0.0120 (15)	0.004 (3)
C2	0.075 (5)	0.064 (4)	0.080 (3)	0.000 (3)	−0.003 (3)	0.024 (3)
C3	0.058 (5)	0.085 (4)	0.104 (5)	−0.017 (3)	−0.004 (3)	0.002 (3)
C4	0.069 (5)	0.096 (5)	0.063 (4)	0.003 (3)	−0.007 (4)	−0.015 (3)
C5	0.073 (4)	0.104 (5)	0.063 (3)	0.003 (3)	−0.017 (3)	0.016 (3)
C6	0.074 (4)	0.068 (4)	0.076 (3)	−0.007 (3)	−0.007 (3)	0.013 (3)
C7	0.100 (5)	0.274 (11)	0.061 (3)	0.040 (5)	−0.025 (3)	0.001 (4)

O1—C8	1.247 (3)	N1—N1i	0.929 (3)
O1—C8i	1.247 (3)	N1—C1	1.413 (6)
C8—C8i	0.854 (4)	N1—H1N	0.883 (15)
C8—C9	1.478 (7)	C1—C2	1.348 (5)
C9—C14	1.362 (6)	C1—C6	1.366 (5)
C9—C10	1.377 (5)	C2—C3	1.368 (7)
C10—C11	1.398 (7)	C2—H2	0.93
C10—H10	0.93	C3—C4	1.363 (7)
C11—C12	1.402 (7)	C3—H3	0.93
C11—H11	0.93	C4—C5	1.352 (7)
C12—C13	1.400 (6)	C4—C7	1.447 (14)
C12—C15	1.567 (11)	C5—C6	1.363 (8)
C13—C14	1.398 (10)	C5—H5	0.93
C13—H13	0.93	C6—H6	0.93
C14—H14	0.93	C7—H7A	0.96
C15—H15A	0.96	C7—H7B	0.96
C15—H15B	0.96	C7—H7C	0.96
C15—H15C	0.96
C8i—C8—C9	162.2 (4)	C2—C1—N1	124.5 (6)
O1—C8—C9	125.3 (3)	C6—C1—N1	118.2 (6)
C14—C9—C10	118.4 (6)	C1—C2—C3	121.3 (9)
C14—C9—C8	124.6 (6)	C1—C2—H2	119.3
C10—C9—C8	117.0 (6)	C3—C2—H2	119.3
C9—C10—C11	120.4 (9)	C4—C3—C2	124.5 (12)
C9—C10—H10	119.8	C4—C3—H3	117.8
C11—C10—H10	119.8	C2—C3—H3	117.8
C10—C11—C12	120.2 (11)	C5—C4—C3	111.0 (12)
C10—C11—H11	119.9	C5—C4—C7	119.5 (11)
C12—C11—H11	119.9	C3—C4—C7	129.0 (10)
C13—C12—C11	119.9 (10)	C4—C5—C6	127.8 (13)
C13—C12—C15	124.9 (9)	C4—C5—H5	116.1
C11—C12—C15	114.9 (8)	C6—C5—H5	116.1
C14—C13—C12	116.9 (10)	C5—C6—C1	118.1 (10)
C14—C13—H13	121.5	C5—C6—H6	121
C12—C13—H13	121.5	C1—C6—H6	121
C9—C14—C13	124.1 (8)	C4—C7—H7A	109.5
C9—C14—H14	117.9	C4—C7—H7B	109.5
C13—C14—H14	117.9	H7A—C7—H7B	109.5
N1i—N1—C1	172.2 (4)	C4—C7—H7C	109.5
N1i—N1—H1N	58.3 (7)	H7A—C7—H7C	109.5
C1—N1—H1N	124.7 (6)	H7B—C7—H7C	109.5
C2—C1—C6	117.2 (6)
C8i—O1—C8—C9	169.7 (6)	C8—C9—C14—C13	−178.6 (11)
C8i—C8—C9—C14	1.0 (19)	C12—C13—C14—C9	0(2)
O1—C8—C9—C14	−145.7 (6)	C6—C1—C2—C3	0.1 (17)
C8i—C8—C9—C10	−177.5 (15)	N1—C1—C2—C3	176.9 (10)
O1—C8—C9—C10	35.8 (9)	C1—C2—C3—C4	0(3)
C14—C9—C10—C11	0.6 (15)	C2—C3—C4—C5	1(3)
C8—C9—C10—C11	179.2 (9)	C2—C3—C4—C7	−170.1 (17)
C9—C10—C11—C12	−1(2)	C3—C4—C5—C6	−3(3)
C10—C11—C12—C13	0(3)	C7—C4—C5—C6	169.1 (16)
C10—C11—C12—C15	175.0 (12)	C4—C5—C6—C1	4(3)
C11—C12—C13—C14	0(3)	C2—C1—C6—C5	−1.7 (15)
C15—C12—C13—C14	−174.0 (15)	N1—C1—C6—C5	−178.8 (10)
C10—C9—C14—C13	−0.2 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ii	0.88 (2)	2.42 (2)	3.202 (3)	148 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.883 (15)	2.416 (19)	3.202 (3)	148.3 (6)

Symmetry code: (i) .