N-(2,4-Dimethyl-phen-yl)-4-methyl-benzamide.

In the mol-ecule of the title compound, C(16)H(17)NO, the N-H and C=O bonds are anti to each other and the two benzene rings form a dihedral angle of 75.8 (1)°. The amide group is twisted by 28.1 (3) and 76.3 (2)° out of the planes of the 4-methyl-phenyl and 2,4-dimethyl-phenyl rings, respectively. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into chains running along the c axis. The crystal studied was hemihedrally twinned with a twin law resulting from a twofold rotation about the a axis.

Related literature

For the preparation, see: Gowda et al. (2003 ▶). For related structures, see: Bowes et al. (2003 ▶); Gowda et al. (2003 ▶, 2009 ▶, 2010 ▶).

Experimental

Crystal data

C16H17NO

M = 239.31

Monoclinic,

a = 22.4974 (17) Å

b = 6.6033 (2) Å

c = 9.2474 (6) Å

β = 100.209 (6)°

V = 1352.02 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 295 K

0.33 × 0.22 × 0.03 mm

Data collection

Oxford Diffraction Xcalibur, Ruby, Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.983, T max = 0.998

12970 measured reflections

3430 independent reflections

2107 reflections with I > 2σ(I)

R int = 0.079

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.192

S = 1.03

3430 reflections

167 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.18 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/S1600536810013413/tk2655sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013413/tk2655Isup2.hkl

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

C16H17NO	F(000) = 512
Mr = 239.31	Dx = 1.176 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3071 reflections
a = 22.4974 (17) Å	θ = 1.8–29.6°
b = 6.6033 (2) Å	µ = 0.07 mm−1
c = 9.2474 (6) Å	T = 295 K
β = 100.209 (6)°	Plate, colourless
V = 1352.02 (14) Å3	0.33 × 0.22 × 0.03 mm
Z = 4

Oxford Diffraction Xcalibur, Ruby, Gemini diffractometer	3430 independent reflections
graphite	2107 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1	Rint = 0.079
ω scans	θmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −26→26
Tmin = 0.983, Tmax = 0.998	k = −7→7
12970 measured reflections	l = −9→11

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.192	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0864P)2] where P = (Fo2 + 2Fc2)/3
3430 reflections	(Δ/σ)max < 0.001
167 parameters	Δρmax = 0.21 e Å−3
1 restraint	Δρmin = −0.17 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.19951 (16)	0.4402 (5)	−0.0180 (3)	0.0468 (9)
C2	0.14244 (17)	0.3963 (5)	0.0076 (4)	0.0515 (9)
C3	0.09535 (16)	0.5225 (6)	−0.0511 (4)	0.0567 (10)
H3	0.0565	0.4918	−0.0368	0.068*
C4	0.10472 (18)	0.6947 (6)	−0.1314 (4)	0.0600 (10)
C5	0.16235 (19)	0.7348 (7)	−0.1540 (4)	0.0645 (11)
H5	0.1695	0.8486	−0.2077	0.077*
C6	0.20935 (17)	0.6099 (6)	−0.0986 (4)	0.0545 (10)
H6	0.248	0.6389	−0.1151	0.065*
C7	0.27622 (16)	0.2919 (5)	0.1727 (4)	0.0492 (9)
C8	0.32400 (15)	0.1339 (5)	0.2078 (4)	0.0465 (9)
C9	0.32238 (18)	−0.0436 (6)	0.1290 (4)	0.0679 (11)
H9	0.2925	−0.0637	0.0469	0.081*
C10	0.3653 (2)	−0.1920 (6)	0.1721 (5)	0.0699 (12)
H10	0.363	−0.3127	0.1195	0.084*
C11	0.41057 (18)	−0.1669 (6)	0.2888 (5)	0.0674 (12)
C12	0.41121 (17)	0.0115 (7)	0.3662 (4)	0.0702 (11)
H12	0.4417	0.0333	0.4467	0.084*
C13	0.36811 (16)	0.1577 (6)	0.3279 (4)	0.0596 (11)
H13	0.369	0.2745	0.3844	0.072*
C14	0.13012 (19)	0.2119 (6)	0.0952 (5)	0.0733 (12)
H14A	0.1481	0.2305	0.1965	0.11*
H14B	0.1472	0.0942	0.0573	0.11*
H14C	0.0873	0.1942	0.0872	0.11*
C15	0.0514 (2)	0.8274 (7)	−0.1942 (5)	0.0921 (16)
H15A	0.0653	0.9622	−0.2082	0.138*
H15B	0.0233	0.8306	−0.1274	0.138*
H15C	0.0319	0.7733	−0.2869	0.138*
C16	0.4581 (2)	−0.3282 (7)	0.3361 (6)	0.1064 (17)
H16A	0.4485	−0.4471	0.2769	0.16*
H16B	0.459	−0.3615	0.4375	0.16*
H16C	0.497	−0.2779	0.3239	0.16*
N1	0.24865 (13)	0.3076 (4)	0.0336 (3)	0.0561 (8)
H1N	0.2615	0.232	−0.0301	0.067*
O1	0.26376 (11)	0.4035 (4)	0.2695 (3)	0.0578 (7)

	U11	U22	U33	U12	U13	U23
C1	0.056 (2)	0.056 (2)	0.0281 (19)	0.0081 (18)	0.0065 (16)	−0.0041 (17)
C2	0.069 (3)	0.055 (2)	0.029 (2)	0.0028 (19)	0.0041 (17)	−0.0007 (17)
C3	0.058 (2)	0.066 (3)	0.043 (2)	−0.005 (2)	0.0023 (17)	−0.005 (2)
C4	0.067 (3)	0.052 (3)	0.056 (3)	0.007 (2)	−0.0004 (19)	0.000 (2)
C5	0.080 (3)	0.056 (2)	0.057 (3)	−0.003 (2)	0.010 (2)	0.008 (2)
C6	0.063 (2)	0.056 (2)	0.044 (2)	−0.013 (2)	0.0079 (17)	−0.0021 (19)
C7	0.067 (2)	0.056 (2)	0.026 (2)	−0.0060 (17)	0.0125 (17)	−0.0031 (18)
C8	0.056 (2)	0.050 (2)	0.035 (2)	−0.0034 (15)	0.0135 (17)	0.0004 (17)
C9	0.087 (3)	0.059 (3)	0.053 (3)	0.005 (2)	0.002 (2)	−0.003 (2)
C10	0.090 (3)	0.051 (3)	0.068 (3)	0.008 (2)	0.011 (2)	−0.009 (2)
C11	0.068 (3)	0.049 (3)	0.087 (3)	0.006 (2)	0.016 (2)	0.013 (2)
C12	0.055 (2)	0.083 (3)	0.066 (3)	0.005 (2)	−0.0048 (19)	−0.001 (2)
C13	0.056 (2)	0.064 (3)	0.054 (2)	−0.003 (2)	−0.002 (2)	−0.012 (2)
C14	0.094 (3)	0.064 (3)	0.066 (3)	−0.003 (2)	0.025 (2)	0.014 (2)
C15	0.089 (3)	0.091 (4)	0.094 (4)	0.021 (3)	0.010 (3)	0.018 (3)
C16	0.099 (4)	0.093 (4)	0.124 (5)	0.021 (3)	0.011 (3)	0.013 (3)
N1	0.073 (2)	0.063 (2)	0.0321 (18)	0.0104 (17)	0.0092 (15)	0.0008 (15)
O1	0.0831 (18)	0.0566 (14)	0.0335 (13)	0.0090 (13)	0.0096 (12)	−0.0010 (13)

C1—C2	1.377 (5)	C9—H9	0.93
C1—C6	1.385 (5)	C10—C11	1.357 (6)
C1—N1	1.424 (4)	C10—H10	0.93
C2—C3	1.381 (5)	C11—C12	1.377 (5)
C2—C14	1.514 (5)	C11—C16	1.518 (5)
C3—C4	1.394 (5)	C12—C13	1.370 (5)
C3—H3	0.93	C12—H12	0.93
C4—C5	1.375 (5)	C13—H13	0.93
C4—C15	1.515 (5)	C14—H14A	0.96
C5—C6	1.367 (5)	C14—H14B	0.96
C5—H5	0.93	C14—H14C	0.96
C6—H6	0.93	C15—H15A	0.96
C7—O1	1.230 (4)	C15—H15B	0.96
C7—N1	1.329 (4)	C15—H15C	0.96
C7—C8	1.492 (5)	C16—H16A	0.96
C8—C13	1.360 (5)	C16—H16B	0.96
C8—C9	1.377 (5)	C16—H16C	0.96
C9—C10	1.384 (5)	N1—H1N	0.86
C2—C1—C6	120.4 (3)	C10—C11—C12	117.1 (4)
C2—C1—N1	120.3 (3)	C10—C11—C16	122.4 (4)
C6—C1—N1	119.3 (3)	C12—C11—C16	120.6 (4)
C1—C2—C3	118.6 (3)	C13—C12—C11	121.8 (4)
C1—C2—C14	121.7 (3)	C13—C12—H12	119.1
C3—C2—C14	119.7 (4)	C11—C12—H12	119.1
C2—C3—C4	121.6 (4)	C8—C13—C12	120.7 (4)
C2—C3—H3	119.2	C8—C13—H13	119.7
C4—C3—H3	119.2	C12—C13—H13	119.7
C5—C4—C3	118.3 (3)	C2—C14—H14A	109.5
C5—C4—C15	122.2 (4)	C2—C14—H14B	109.5
C3—C4—C15	119.5 (4)	H14A—C14—H14B	109.5
C6—C5—C4	120.9 (4)	C2—C14—H14C	109.5
C6—C5—H5	119.5	H14A—C14—H14C	109.5
C4—C5—H5	119.5	H14B—C14—H14C	109.5
C5—C6—C1	120.2 (4)	C4—C15—H15A	109.5
C5—C6—H6	119.9	C4—C15—H15B	109.5
C1—C6—H6	119.9	H15A—C15—H15B	109.5
O1—C7—N1	122.0 (3)	C4—C15—H15C	109.5
O1—C7—C8	120.6 (3)	H15A—C15—H15C	109.5
N1—C7—C8	117.4 (3)	H15B—C15—H15C	109.5
C13—C8—C9	118.5 (3)	C11—C16—H16A	109.5
C13—C8—C7	119.3 (3)	C11—C16—H16B	109.5
C9—C8—C7	122.0 (3)	H16A—C16—H16B	109.5
C8—C9—C10	119.9 (4)	C11—C16—H16C	109.5
C8—C9—H9	120.1	H16A—C16—H16C	109.5
C10—C9—H9	120.1	H16B—C16—H16C	109.5
C11—C10—C9	122.0 (4)	C7—N1—C1	125.0 (3)
C11—C10—H10	119	C7—N1—H1N	117.5
C9—C10—H10	119	C1—N1—H1N	117.5
C6—C1—C2—C3	1.3 (5)	N1—C7—C8—C9	−29.8 (5)
N1—C1—C2—C3	−176.4 (3)	C13—C8—C9—C10	−0.4 (6)
C6—C1—C2—C14	179.9 (3)	C7—C8—C9—C10	−175.4 (4)
N1—C1—C2—C14	2.2 (5)	C8—C9—C10—C11	−1.8 (7)
C1—C2—C3—C4	−1.9 (5)	C9—C10—C11—C12	1.9 (6)
C14—C2—C3—C4	179.5 (3)	C9—C10—C11—C16	−179.4 (4)
C2—C3—C4—C5	1.4 (5)	C10—C11—C12—C13	0.1 (6)
C2—C3—C4—C15	179.7 (4)	C16—C11—C12—C13	−178.6 (4)
C3—C4—C5—C6	−0.3 (6)	C9—C8—C13—C12	2.3 (6)
C15—C4—C5—C6	−178.6 (4)	C7—C8—C13—C12	177.4 (3)
C4—C5—C6—C1	−0.2 (6)	C11—C12—C13—C8	−2.2 (6)
C2—C1—C6—C5	−0.3 (5)	O1—C7—N1—C1	−5.1 (6)
N1—C1—C6—C5	177.5 (3)	C8—C7—N1—C1	175.7 (3)
O1—C7—C8—C13	−24.1 (5)	C2—C1—N1—C7	−75.0 (4)
N1—C7—C8—C13	155.2 (3)	C6—C1—N1—C7	107.3 (4)
O1—C7—C8—C9	150.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O1i	0.86	2.07	2.884 (4)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯O1i	0.86	2.07	2.884 (4)	159

Symmetry code: (i) .