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

In the title compound, C(16)H(17)NO, the N-H bond is in an anti conformation with respect to the C=O bonds. The aniline and benzoyl rings are almost coplanar, making a dihedral angle of 4.9 (3)°. The plane of the amide group makes an angle of 61.3 (3)° with the aniline ring and 58.3 (3)° with the benzoyl ring. In the crystal, the mol-ecules are linked by N-H⋯O hydrogen bonds into chains running along the b axis.

Related literature

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

Experimental

Crystal data

C16H17NO

M = 239.31

Orthorhombic,

a = 6.0062 (4) Å

b = 9.8036 (6) Å

c = 44.943 (4) Å

V = 2646.4 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.53 × 0.48 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur System diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.958, T max = 0.991

20129 measured reflections

2467 independent reflections

1863 reflections with I > 2σ(I)

R int = 0.073

Refinement

R[F 2 > 2σ(F 2)] = 0.098

wR(F 2) = 0.241

S = 1.14

2467 reflections

169 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); 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/S1600536809009830/bt2892sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809009830/bt2892Isup2.hkl

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

C16H17NO	F(000) = 1024
Mr = 239.31	Dx = 1.201 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 7082 reflections
a = 6.0062 (4) Å	θ = 3.2–27.5°
b = 9.8036 (6) Å	µ = 0.08 mm−1
c = 44.943 (4) Å	T = 295 K
V = 2646.4 (3) Å3	Block, colourless
Z = 8	0.53 × 0.48 × 0.12 mm

Oxford Diffraction Xcalibur System diffractometer	2467 independent reflections
graphite	1863 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1	Rint = 0.073
ω scans with κ offsets	θmax = 25.7°, θmin = 3.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	h = −7→7
Tmin = 0.958, Tmax = 0.991	k = −11→11
20129 measured reflections	l = −54→54

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)] = 0.098	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.241	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ2(Fo2) + (0.0735P)2 + 4.7656P] where P = (Fo2 + 2Fc2)/3
2467 reflections	(Δ/σ)max < 0.001
169 parameters	Δρmax = 0.24 e Å−3
1 restraint	Δρmin = −0.20 e Å−3

Experimental. CrysAlis RED (Oxford Diffraction, 2008). Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.4332 (7)	0.5763 (4)	0.09991 (8)	0.0446 (9)
C2	0.3831 (7)	0.5294 (4)	0.07156 (9)	0.0470 (9)
C3	0.5158 (7)	0.5746 (4)	0.04829 (9)	0.0501 (10)
H3	0.4813	0.5463	0.0291	0.06*
C4	0.6975 (7)	0.6600 (5)	0.05232 (9)	0.0557 (11)
C5	0.7436 (7)	0.7029 (4)	0.08089 (9)	0.0543 (10)
H5	0.8635	0.761	0.0843	0.065*
C6	0.6148 (7)	0.6611 (4)	0.10447 (9)	0.0501 (10)
H6	0.6498	0.6898	0.1236	0.06*
C7	0.1870 (7)	0.6237 (3)	0.14167 (8)	0.0442 (9)
C8	0.0506 (6)	0.5613 (4)	0.16578 (8)	0.0442 (9)
C9	0.0815 (7)	0.5979 (4)	0.19532 (9)	0.0533 (10)
C10	−0.0551 (9)	0.5371 (5)	0.21657 (10)	0.0712 (14)
H10	−0.0356	0.5587	0.2366	0.085*
C11	−0.2191 (9)	0.4454 (5)	0.20853 (12)	0.0743 (14)
H11	−0.311	0.4081	0.2231	0.089*
C12	−0.2471 (9)	0.4092 (5)	0.17960 (11)	0.0711 (13)
H12	−0.3568	0.3468	0.1743	0.085*
C13	−0.1125 (7)	0.4655 (4)	0.15833 (10)	0.0542 (10)
H13	−0.1298	0.4396	0.1386	0.065*
C14	0.1901 (7)	0.4363 (4)	0.06628 (10)	0.0589 (11)
H14A	0.1679	0.4252	0.0453	0.088*
H14B	0.0585	0.4749	0.075	0.088*
H14C	0.2199	0.3492	0.0752	0.088*
C15	0.8378 (9)	0.7033 (5)	0.02654 (11)	0.0769 (15)
H15A	0.9908	0.7082	0.0326	0.115*
H15B	0.7899	0.7913	0.0197	0.115*
H15C	0.823	0.6381	0.0107	0.115*
C16	0.2558 (10)	0.6978 (5)	0.20471 (10)	0.0754 (14)
H16A	0.4004	0.6625	0.1999	0.113*
H16B	0.2459	0.7124	0.2258	0.113*
H16C	0.2331	0.7827	0.1945	0.113*
N1	0.3000 (6)	0.5350 (3)	0.12468 (7)	0.0491 (9)
H1N	0.287 (7)	0.445 (3)	0.1279 (8)	0.059*
O1	0.1884 (5)	0.7473 (3)	0.13756 (6)	0.0638 (9)

	U11	U22	U33	U12	U13	U23
C1	0.046 (2)	0.0306 (18)	0.057 (2)	0.0064 (17)	0.0054 (18)	0.0037 (16)
C2	0.043 (2)	0.034 (2)	0.064 (2)	0.0031 (17)	0.0023 (18)	0.0020 (17)
C3	0.052 (2)	0.042 (2)	0.057 (2)	0.001 (2)	−0.0008 (19)	−0.0006 (17)
C4	0.045 (2)	0.058 (3)	0.064 (2)	0.001 (2)	0.0058 (19)	0.010 (2)
C5	0.043 (2)	0.041 (2)	0.079 (3)	−0.0051 (19)	−0.001 (2)	0.002 (2)
C6	0.047 (2)	0.042 (2)	0.060 (2)	0.0015 (18)	−0.0027 (19)	−0.0006 (18)
C7	0.048 (2)	0.0267 (18)	0.058 (2)	0.0048 (17)	−0.0024 (18)	0.0022 (15)
C8	0.045 (2)	0.0311 (18)	0.056 (2)	0.0058 (17)	0.0021 (18)	0.0040 (16)
C9	0.055 (3)	0.041 (2)	0.063 (2)	0.013 (2)	−0.003 (2)	0.0011 (18)
C10	0.088 (4)	0.070 (3)	0.056 (2)	0.025 (3)	0.012 (3)	0.002 (2)
C11	0.073 (3)	0.059 (3)	0.091 (4)	0.006 (3)	0.033 (3)	0.012 (3)
C12	0.056 (3)	0.061 (3)	0.096 (4)	−0.004 (2)	0.014 (3)	0.004 (3)
C13	0.060 (3)	0.032 (2)	0.071 (3)	0.001 (2)	0.004 (2)	0.0011 (18)
C14	0.053 (3)	0.044 (2)	0.080 (3)	−0.013 (2)	0.004 (2)	−0.005 (2)
C15	0.069 (3)	0.077 (3)	0.085 (3)	−0.017 (3)	0.015 (3)	0.011 (3)
C16	0.082 (3)	0.076 (3)	0.068 (3)	0.010 (3)	−0.021 (3)	−0.006 (2)
N1	0.064 (2)	0.0178 (15)	0.0659 (19)	0.0033 (15)	0.0112 (17)	0.0033 (13)
O1	0.080 (2)	0.0284 (14)	0.083 (2)	0.0061 (15)	0.0167 (17)	0.0030 (13)

C1—C6	1.387 (5)	C9—C16	1.494 (7)
C1—C2	1.388 (5)	C10—C11	1.382 (7)
C1—N1	1.430 (5)	C10—H10	0.93
C2—C3	1.388 (5)	C11—C12	1.358 (7)
C2—C14	1.494 (5)	C11—H11	0.93
C3—C4	1.387 (6)	C12—C13	1.369 (6)
C3—H3	0.93	C12—H12	0.93
C4—C5	1.380 (6)	C13—H13	0.93
C4—C15	1.494 (6)	C14—H14A	0.96
C5—C6	1.375 (5)	C14—H14B	0.96
C5—H5	0.93	C14—H14C	0.96
C6—H6	0.93	C15—H15A	0.96
C7—O1	1.225 (4)	C15—H15B	0.96
C7—N1	1.342 (5)	C15—H15C	0.96
C7—C8	1.490 (5)	C16—H16A	0.96
C8—C9	1.388 (5)	C16—H16B	0.96
C8—C13	1.398 (5)	C16—H16C	0.96
C9—C10	1.393 (6)	N1—H1N	0.90 (3)
C6—C1—C2	120.3 (4)	C12—C11—C10	120.6 (5)
C6—C1—N1	119.7 (3)	C12—C11—H11	119.7
C2—C1—N1	120.0 (4)	C10—C11—H11	119.7
C3—C2—C1	117.5 (4)	C11—C12—C13	119.3 (5)
C3—C2—C14	121.4 (4)	C11—C12—H12	120.3
C1—C2—C14	121.1 (4)	C13—C12—H12	120.3
C4—C3—C2	123.1 (4)	C12—C13—C8	121.2 (4)
C4—C3—H3	118.4	C12—C13—H13	119.4
C2—C3—H3	118.4	C8—C13—H13	119.4
C5—C4—C3	117.6 (4)	C2—C14—H14A	109.5
C5—C4—C15	121.5 (4)	C2—C14—H14B	109.5
C3—C4—C15	120.9 (4)	H14A—C14—H14B	109.5
C6—C5—C4	120.9 (4)	C2—C14—H14C	109.5
C6—C5—H5	119.6	H14A—C14—H14C	109.5
C4—C5—H5	119.6	H14B—C14—H14C	109.5
C5—C6—C1	120.5 (4)	C4—C15—H15A	109.5
C5—C6—H6	119.7	C4—C15—H15B	109.5
C1—C6—H6	119.7	H15A—C15—H15B	109.5
O1—C7—N1	123.5 (4)	C4—C15—H15C	109.5
O1—C7—C8	121.3 (3)	H15A—C15—H15C	109.5
N1—C7—C8	115.2 (3)	H15B—C15—H15C	109.5
C9—C8—C13	119.8 (4)	C9—C16—H16A	109.5
C9—C8—C7	121.0 (4)	C9—C16—H16B	109.5
C13—C8—C7	119.2 (3)	H16A—C16—H16B	109.5
C8—C9—C10	117.8 (4)	C9—C16—H16C	109.5
C8—C9—C16	122.3 (4)	H16A—C16—H16C	109.5
C10—C9—C16	120.0 (4)	H16B—C16—H16C	109.5
C11—C10—C9	121.3 (4)	C7—N1—C1	122.8 (3)
C11—C10—H10	119.4	C7—N1—H1N	120 (3)
C9—C10—H10	119.4	C1—N1—H1N	117 (3)
C6—C1—C2—C3	−2.3 (5)	N1—C7—C8—C13	−57.5 (5)
N1—C1—C2—C3	179.0 (3)	C13—C8—C9—C10	−0.4 (6)
C6—C1—C2—C14	179.1 (4)	C7—C8—C9—C10	178.8 (4)
N1—C1—C2—C14	0.4 (5)	C13—C8—C9—C16	178.9 (4)
C1—C2—C3—C4	2.0 (6)	C7—C8—C9—C16	−1.9 (6)
C14—C2—C3—C4	−179.4 (4)	C8—C9—C10—C11	−1.3 (6)
C2—C3—C4—C5	−1.2 (6)	C16—C9—C10—C11	179.4 (4)
C2—C3—C4—C15	178.7 (4)	C9—C10—C11—C12	1.8 (7)
C3—C4—C5—C6	0.7 (6)	C10—C11—C12—C13	−0.6 (7)
C15—C4—C5—C6	−179.2 (4)	C11—C12—C13—C8	−1.1 (7)
C4—C5—C6—C1	−1.0 (6)	C9—C8—C13—C12	1.6 (6)
C2—C1—C6—C5	1.9 (6)	C7—C8—C13—C12	−177.6 (4)
N1—C1—C6—C5	−179.4 (3)	O1—C7—N1—C1	−0.2 (6)
O1—C7—C8—C9	−58.6 (5)	C8—C7—N1—C1	177.8 (4)
N1—C7—C8—C9	123.3 (4)	C6—C1—N1—C7	62.0 (5)
O1—C7—C8—C13	120.6 (4)	C2—C1—N1—C7	−119.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.90 (3)	1.99 (3)	2.880 (4)	170 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.90 (3)	1.99 (3)	2.880 (4)	170 (4)

Symmetry code: (i) .