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

The conformations of the N-H and C=O bonds in the structure of the title compound, C(15)H(15)NO, are trans to each other. Furthermore, the position of the amide O atom is syn to the ortho-methyl group in the benzoyl ring. The central amide group is tilted at an angle of 59.96 (11)° to the benzoyl ring, and the benzoyl and aniline rings form a dihedral angle of 81.44 (5)°. N-H⋯O hydrogen bonds link the mol-ecules into infinite chains running along the c axis.

Related literature

For related literature, see Gowda et al. (2003 ▶, 2008 ▶,c ▶).

Experimental

Crystal data

C15H15NO

M = 225.28

Monoclinic,

a = 40.6634 (12) Å

b = 7.1770 (2) Å

c = 8.9418 (2) Å

β = 96.173 (3)°

V = 2594.45 (12) Å3

Z = 8

Mo Kα radiation

μ = 0.07 mm−1

T = 295 (2) K

0.33 × 0.13 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur System diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.985, T max = 0.994

25372 measured reflections

2486 independent reflections

1594 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.121

S = 1.02

2486 reflections

159 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.11 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, 2003 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808021235/tk2283sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021235/tk2283Isup2.hkl

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

C15H15NO	F000 = 960
Mr = 225.28	Dx = 1.153 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6446 reflections
a = 40.6634 (12) Å	θ = 3.0–29.2º
b = 7.1770 (2) Å	µ = 0.07 mm−1
c = 8.9418 (2) Å	T = 295 (2) K
β = 96.173 (3)º	Prism, colourless
V = 2594.45 (12) Å3	0.33 × 0.13 × 0.10 mm
Z = 8

Oxford Diffraction Xcalibur System diffractometer	2486 independent reflections
Monochromator: graphite	1594 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1	Rint = 0.049
T = 295(2) K	θmax = 25.9º
ω scans with κ offsets	θmin = 5.4º
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2007)	h = −49→49
Tmin = 0.985, Tmax = 0.994	k = −8→8
25372 measured reflections	l = −10→10

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)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.121	w = 1/[σ2(Fo2) + (0.0661P)2 + 0.0615P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
2486 reflections	Δρmax = 0.13 e Å−3
159 parameters	Δρmin = −0.11 e Å−3
4 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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)
C1	0.38556 (4)	0.3947 (2)	0.51508 (15)	0.0490 (4)
C2	0.41020 (4)	0.29352 (18)	0.43275 (14)	0.0460 (4)
C3	0.44366 (4)	0.2966 (2)	0.48505 (16)	0.0556 (4)
C4	0.46488 (4)	0.1922 (2)	0.4075 (2)	0.0683 (5)
H4	0.4874	0.193	0.4397	0.082*
C5	0.45356 (5)	0.0877 (2)	0.2846 (2)	0.0744 (5)
H5	0.4683	0.0168	0.236	0.089*
C6	0.42084 (5)	0.0867 (2)	0.23294 (19)	0.0712 (5)
H6	0.4132	0.0166	0.1488	0.085*
C7	0.39921 (4)	0.1908 (2)	0.30672 (15)	0.0577 (4)
H7	0.3769	0.192	0.2712	0.069*
C8	0.34387 (4)	0.6436 (2)	0.48652 (14)	0.0508 (4)
C9	0.32161 (4)	0.5851 (2)	0.58239 (17)	0.0654 (5)
H9	0.3219	0.4626	0.6163	0.078*
C10	0.29882 (4)	0.7110 (3)	0.6277 (2)	0.0785 (5)
H10	0.2839	0.6706	0.6926	0.094*
C11	0.29747 (4)	0.8930 (3)	0.5804 (2)	0.0752 (5)
C12	0.32004 (5)	0.9467 (3)	0.4855 (2)	0.0799 (5)
H12	0.3199	1.0694	0.452	0.096*
C13	0.34283 (4)	0.8252 (3)	0.43868 (18)	0.0697 (5)
H13	0.3577	0.8664	0.3739	0.084*
C14	0.45688 (5)	0.4126 (3)	0.6189 (2)	0.0896 (6)
H14A	0.4806	0.4132	0.6273	0.134*
H14B	0.4496	0.3606	0.7087	0.134*
H14C	0.4488	0.538	0.606	0.134*
C15	0.27185 (5)	1.0262 (4)	0.6292 (3)	0.1144 (9)
H15A	0.2567	0.9594	0.6848	0.172*	0.5
H15B	0.2599	1.0821	0.542	0.172*	0.5
H15C	0.2826	1.1217	0.6917	0.172*	0.5
H15D	0.2761	1.1494	0.5942	0.172*	0.5
H15E	0.2729	1.0267	0.737	0.172*	0.5
H15F	0.2502	0.9871	0.5873	0.172*	0.5
N1	0.36770 (3)	0.52332 (18)	0.43453 (13)	0.0545 (4)
H1N	0.3735 (4)	0.552 (2)	0.3467 (15)	0.065*
O1	0.38239 (3)	0.35884 (16)	0.64635 (11)	0.0718 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0637 (9)	0.0501 (9)	0.0351 (7)	−0.0025 (7)	0.0132 (6)	−0.0003 (6)
C2	0.0611 (9)	0.0411 (8)	0.0374 (7)	0.0016 (7)	0.0133 (6)	0.0030 (6)
C3	0.0646 (10)	0.0491 (9)	0.0537 (9)	0.0001 (8)	0.0091 (7)	−0.0005 (7)
C4	0.0587 (10)	0.0634 (11)	0.0843 (12)	0.0030 (9)	0.0147 (9)	0.0005 (9)
C5	0.0779 (13)	0.0625 (12)	0.0871 (12)	0.0077 (10)	0.0293 (10)	−0.0164 (10)
C6	0.0846 (13)	0.0660 (12)	0.0653 (10)	−0.0002 (10)	0.0184 (9)	−0.0243 (9)
C7	0.0645 (10)	0.0597 (10)	0.0500 (8)	−0.0019 (8)	0.0107 (7)	−0.0079 (7)
C8	0.0518 (9)	0.0636 (10)	0.0376 (7)	0.0047 (8)	0.0082 (6)	−0.0023 (7)
C9	0.0613 (10)	0.0722 (11)	0.0655 (9)	−0.0040 (8)	0.0205 (8)	−0.0039 (8)
C10	0.0576 (10)	0.1063 (15)	0.0759 (11)	−0.0022 (10)	0.0265 (8)	−0.0135 (10)
C11	0.0625 (11)	0.0948 (13)	0.0667 (11)	0.0212 (10)	−0.0003 (9)	−0.0204 (10)
C12	0.0887 (13)	0.0752 (13)	0.0761 (11)	0.0250 (11)	0.0104 (10)	0.0027 (10)
C13	0.0773 (12)	0.0708 (12)	0.0641 (10)	0.0136 (10)	0.0214 (8)	0.0106 (9)
C14	0.0823 (13)	0.0965 (15)	0.0864 (12)	−0.0020 (11)	−0.0075 (10)	−0.0278 (11)
C15	0.0884 (15)	0.146 (2)	0.1076 (15)	0.0512 (15)	0.0038 (12)	−0.0354 (15)
N1	0.0660 (8)	0.0652 (9)	0.0352 (6)	0.0115 (7)	0.0185 (6)	0.0062 (6)
O1	0.1041 (9)	0.0757 (8)	0.0394 (6)	0.0222 (7)	0.0253 (5)	0.0099 (5)

C1—O1	1.2219 (15)	C9—H9	0.93
C1—N1	1.3362 (18)	C10—C11	1.372 (3)
C1—C2	1.4941 (19)	C10—H10	0.93
C2—C7	1.380 (2)	C11—C12	1.370 (3)
C2—C3	1.390 (2)	C11—C15	1.513 (3)
C3—C4	1.384 (2)	C12—C13	1.371 (2)
C3—C14	1.509 (2)	C12—H12	0.93
C4—C5	1.369 (2)	C13—H13	0.93
C4—H4	0.93	C14—H14A	0.96
C5—C6	1.361 (2)	C14—H14B	0.96
C5—H5	0.93	C14—H14C	0.96
C6—C7	1.375 (2)	C15—H15A	0.96
C6—H6	0.93	C15—H15B	0.96
C7—H7	0.93	C15—H15C	0.96
C8—C13	1.372 (2)	C15—H15D	0.96
C8—C9	1.377 (2)	C15—H15E	0.96
C8—N1	1.4132 (19)	C15—H15F	0.96
C9—C10	1.386 (2)	N1—H1N	0.868 (13)
O1—C1—N1	123.78 (13)	C13—C12—H12	119
O1—C1—C2	121.10 (13)	C12—C13—C8	120.57 (17)
N1—C1—C2	115.12 (11)	C12—C13—H13	119.7
C7—C2—C3	120.17 (13)	C8—C13—H13	119.7
C7—C2—C1	119.10 (13)	C3—C14—H14A	109.5
C3—C2—C1	120.69 (12)	C3—C14—H14B	109.5
C4—C3—C2	117.58 (14)	H14A—C14—H14B	109.5
C4—C3—C14	120.54 (15)	C3—C14—H14C	109.5
C2—C3—C14	121.86 (14)	H14A—C14—H14C	109.5
C5—C4—C3	121.66 (16)	H14B—C14—H14C	109.5
C5—C4—H4	119.2	C11—C15—H15A	109.5
C3—C4—H4	119.2	C11—C15—H15B	109.5
C6—C5—C4	120.51 (15)	H15A—C15—H15B	109.5
C6—C5—H5	119.7	C11—C15—H15C	109.5
C4—C5—H5	119.7	H15A—C15—H15C	109.5
C5—C6—C7	119.13 (15)	H15B—C15—H15C	109.5
C5—C6—H6	120.4	C11—C15—H15D	109.5
C7—C6—H6	120.4	H15A—C15—H15D	141.1
C6—C7—C2	120.93 (15)	H15B—C15—H15D	56.3
C6—C7—H7	119.5	H15C—C15—H15D	56.3
C2—C7—H7	119.5	C11—C15—H15E	109.5
C13—C8—C9	118.91 (15)	H15A—C15—H15E	56.3
C13—C8—N1	118.50 (14)	H15B—C15—H15E	141.1
C9—C8—N1	122.59 (15)	H15C—C15—H15E	56.3
C8—C9—C10	119.25 (17)	H15D—C15—H15E	109.5
C8—C9—H9	120.4	C11—C15—H15F	109.5
C10—C9—H9	120.4	H15A—C15—H15F	56.3
C11—C10—C9	122.42 (17)	H15B—C15—H15F	56.3
C11—C10—H10	118.8	H15C—C15—H15F	141.1
C9—C10—H10	118.8	H15D—C15—H15F	109.5
C12—C11—C10	116.86 (16)	H15E—C15—H15F	109.5
C12—C11—C15	121.9 (2)	C1—N1—C8	126.63 (12)
C10—C11—C15	121.3 (2)	C1—N1—H1N	117.8 (11)
C11—C12—C13	122.00 (18)	C8—N1—H1N	114.6 (11)
C11—C12—H12	119
O1—C1—C2—C7	118.96 (16)	C13—C8—C9—C10	0.0 (2)
N1—C1—C2—C7	−60.69 (18)	N1—C8—C9—C10	−179.59 (14)
O1—C1—C2—C3	−58.66 (19)	C8—C9—C10—C11	0.1 (3)
N1—C1—C2—C3	121.68 (15)	C9—C10—C11—C12	−0.4 (3)
C7—C2—C3—C4	−0.8 (2)	C9—C10—C11—C15	178.70 (16)
C1—C2—C3—C4	176.82 (14)	C10—C11—C12—C13	0.4 (3)
C7—C2—C3—C14	177.70 (15)	C15—C11—C12—C13	−178.61 (17)
C1—C2—C3—C14	−4.7 (2)	C11—C12—C13—C8	−0.3 (3)
C2—C3—C4—C5	−0.7 (2)	C9—C8—C13—C12	0.0 (2)
C14—C3—C4—C5	−179.15 (16)	N1—C8—C13—C12	179.69 (14)
C3—C4—C5—C6	1.4 (3)	O1—C1—N1—C8	3.2 (2)
C4—C5—C6—C7	−0.6 (3)	C2—C1—N1—C8	−177.12 (14)
C5—C6—C7—C2	−0.8 (2)	C13—C8—N1—C1	139.57 (16)
C3—C2—C7—C6	1.5 (2)	C9—C8—N1—C1	−40.8 (2)
C1—C2—C7—C6	−176.10 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.868 (13)	1.973 (13)	2.8361 (15)	172.9 (15)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.868 (13)	1.973 (13)	2.8361 (15)	172.9 (15)

Symmetry code: (i) .