N-(2,6-Dimethyl-phen-yl)-4-methyl-benzamide.

In the mol-ecular structure of the title compound, C(16)H(17)NO, the two aromatic rings are close to orthogonal to each other [dihedral angle 78.8 (1)°], while the central -NH-C(=O)- amide core is nearly coplanar with the benzoyl ring, forming a dihedral angle of 3.5 (2)°. Inter-molecular N-H⋯O hydrogen bonds in the crystal structure link the mol-ecules into infinite chains running along the c axis of the crystal, and a C-H⋯O interaction also occurs.

Related literature

For the preparation of the title compound, see: Gowda et al. (2003 ▶). For related structures, see: Gowda, Foro et al. (2008 ▶, 2009 ▶); Gowda, Tokarčík et al. (2008 ▶).

Experimental

Crystal data

C16H17NO

M = 239.31

Tetragonal,

a = 16.6224 (5) Å

c = 19.9508 (7) Å

V = 5512.5 (3) Å3

Z = 16

Mo Kα radiation

μ = 0.07 mm−1

T = 295 K

0.48 × 0.07 × 0.07 mm

Data collection

Oxford Diffraction Xcalibur diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.977, T max = 0.992

17659 measured reflections

2649 independent reflections

1250 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.108

S = 0.99

2649 reflections

169 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.09 e Å−3

Δρmin = −0.12 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/S1600536809022648/dn2462sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022648/dn2462Isup2.hkl

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

C16H17NO	Dx = 1.153 Mg m−3
Mr = 239.31	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/a	Cell parameters from 3736 reflections
Hall symbol: -I 4ad	θ = 3.2–29.6°
a = 16.6224 (5) Å	µ = 0.07 mm−1
c = 19.9508 (7) Å	T = 295 K
V = 5512.5 (3) Å3	Needle, colourless
Z = 16	0.48 × 0.07 × 0.07 mm
F(000) = 2048

Oxford Diffraction Xcalibur diffractometer	2649 independent reflections
graphite	1250 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1	Rint = 0.039
ω scans with κ offsets	θmax = 25.8°, θmin = 3.2°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	h = −19→20
Tmin = 0.977, Tmax = 0.992	k = −18→20
17659 measured reflections	l = −24→24

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = [exp(2.10(sinθ/λ)2)]/[σ2(Fo2) + (0.0579P)2], where P = 0.33333Fo2 + 0.66667Fc2
2649 reflections	(Δ/σ)max < 0.001
169 parameters	Δρmax = 0.09 e Å−3
2 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)
C1	0.27487 (9)	0.49299 (9)	0.25025 (7)	0.0506 (4)
O1	0.26537 (8)	0.52765 (7)	0.30418 (5)	0.0697 (4)
N1	0.25165 (9)	0.52730 (8)	0.19248 (6)	0.0573 (4)
H1N	0.2648 (10)	0.5037 (9)	0.1539 (7)	0.069*
C2	0.31055 (9)	0.41089 (9)	0.24642 (6)	0.0483 (4)
C3	0.33373 (14)	0.37365 (12)	0.30424 (8)	0.0900 (7)
H3	0.3289	0.4009	0.3448	0.108*
C4	0.36405 (15)	0.29691 (13)	0.30384 (9)	0.0959 (7)
H4	0.3789	0.2735	0.3443	0.115*
C5	0.37308 (10)	0.25407 (10)	0.24670 (9)	0.0606 (5)
C6	0.34988 (13)	0.29146 (12)	0.18953 (9)	0.0828 (6)
H6	0.3548	0.264	0.1491	0.099*
C7	0.31947 (13)	0.36797 (11)	0.18884 (8)	0.0769 (6)
H7	0.3046	0.3911	0.1482	0.092*
C8	0.21647 (11)	0.60581 (10)	0.18922 (7)	0.0565 (4)
C9	0.13575 (12)	0.61467 (10)	0.20521 (7)	0.0630 (5)
C10	0.10337 (13)	0.69090 (13)	0.20139 (10)	0.0801 (6)
H10	0.0496	0.6988	0.2125	0.096*
C11	0.14898 (17)	0.75510 (13)	0.18149 (11)	0.0937 (7)
H11	0.126	0.806	0.1793	0.112*
C12	0.22797 (16)	0.74490 (12)	0.16481 (10)	0.0885 (7)
H12	0.2579	0.7889	0.1505	0.106*
C13	0.26422 (12)	0.66992 (11)	0.16895 (9)	0.0700 (5)
C14	0.40544 (13)	0.16975 (11)	0.24629 (11)	0.0866 (6)
H14A	0.3916	0.1441	0.2047	0.13*	0.5
H14B	0.3825	0.1401	0.2829	0.13*	0.5
H14C	0.4629	0.1711	0.251	0.13*	0.5
H14D	0.4331	0.1594	0.2877	0.13*	0.5
H14E	0.4422	0.1635	0.2095	0.13*	0.5
H14F	0.3618	0.1324	0.2414	0.13*	0.5
C15	0.08424 (12)	0.54478 (13)	0.22548 (10)	0.0842 (6)
H15A	0.0822	0.5064	0.1895	0.126*
H15B	0.0309	0.5634	0.2353	0.126*
H15C	0.1067	0.5197	0.2646	0.126*
C16	0.35125 (14)	0.65809 (14)	0.15300 (11)	0.0971 (7)
H16A	0.3778	0.6338	0.1906	0.146*
H16B	0.3756	0.7092	0.1435	0.146*
H16C	0.3563	0.6237	0.1146	0.146*

	U11	U22	U33	U12	U13	U23
C1	0.0587 (10)	0.0565 (10)	0.0367 (8)	0.0018 (8)	0.0004 (7)	0.0000 (7)
O1	0.1009 (10)	0.0724 (8)	0.0358 (6)	0.0166 (7)	−0.0008 (5)	−0.0073 (5)
N1	0.0802 (10)	0.0571 (9)	0.0347 (6)	0.0149 (7)	−0.0026 (6)	−0.0030 (6)
C2	0.0532 (9)	0.0524 (10)	0.0391 (8)	0.0019 (8)	0.0000 (7)	0.0014 (7)
C3	0.144 (2)	0.0805 (15)	0.0451 (10)	0.0401 (14)	−0.0106 (11)	0.0004 (9)
C4	0.149 (2)	0.0801 (15)	0.0588 (12)	0.0407 (15)	−0.0138 (12)	0.0123 (10)
C5	0.0590 (11)	0.0547 (11)	0.0681 (11)	0.0028 (8)	0.0006 (8)	0.0053 (9)
C6	0.1222 (18)	0.0660 (14)	0.0603 (11)	0.0237 (12)	−0.0004 (11)	−0.0090 (9)
C7	0.1186 (17)	0.0670 (13)	0.0450 (9)	0.0233 (11)	−0.0040 (10)	0.0010 (8)
C8	0.0777 (13)	0.0525 (11)	0.0392 (8)	0.0119 (10)	−0.0078 (8)	−0.0030 (7)
C9	0.0758 (14)	0.0587 (12)	0.0546 (10)	0.0104 (10)	−0.0076 (8)	−0.0021 (8)
C10	0.0811 (14)	0.0717 (15)	0.0874 (13)	0.0192 (12)	−0.0078 (11)	−0.0007 (11)
C11	0.116 (2)	0.0634 (15)	0.1019 (16)	0.0252 (15)	−0.0078 (14)	0.0029 (11)
C12	0.116 (2)	0.0550 (13)	0.0946 (14)	−0.0017 (13)	0.0019 (13)	0.0062 (10)
C13	0.0870 (15)	0.0604 (13)	0.0625 (10)	0.0017 (11)	−0.0007 (9)	−0.0021 (9)
C14	0.0941 (16)	0.0622 (13)	0.1034 (15)	0.0131 (11)	−0.0005 (12)	0.0093 (11)
C15	0.0811 (15)	0.0787 (14)	0.0928 (14)	0.0011 (12)	0.0017 (11)	0.0046 (10)
C16	0.0926 (17)	0.0928 (16)	0.1059 (16)	−0.0052 (13)	0.0143 (13)	−0.0034 (12)

C1—O1	1.2307 (16)	C10—C11	1.368 (3)
C1—N1	1.3427 (17)	C10—H10	0.93
C1—C2	1.490 (2)	C11—C12	1.365 (3)
N1—C8	1.431 (2)	C11—H11	0.93
N1—H1N	0.892 (13)	C12—C13	1.387 (3)
C2—C7	1.360 (2)	C12—H12	0.93
C2—C3	1.365 (2)	C13—C16	1.494 (3)
C3—C4	1.372 (3)	C14—H14A	0.96
C3—H3	0.93	C14—H14B	0.96
C4—C5	1.352 (2)	C14—H14C	0.96
C4—H4	0.93	C14—H14D	0.96
C5—C6	1.355 (2)	C14—H14E	0.96
C5—C14	1.501 (2)	C14—H14F	0.96
C6—C7	1.369 (3)	C15—H15A	0.96
C6—H6	0.93	C15—H15B	0.96
C7—H7	0.93	C15—H15C	0.96
C8—C9	1.387 (2)	C16—H16A	0.96
C8—C13	1.389 (2)	C16—H16B	0.96
C9—C10	1.379 (2)	C16—H16C	0.96
C9—C15	1.499 (3)
O1—C1—N1	120.98 (15)	C13—C12—H12	119.5
O1—C1—C2	121.65 (13)	C12—C13—C8	117.29 (19)
N1—C1—C2	117.35 (13)	C12—C13—C16	121.75 (19)
C1—N1—C8	122.94 (12)	C8—C13—C16	120.95 (18)
C1—N1—H1N	119.0 (11)	C5—C14—H14A	109.5
C8—N1—H1N	117.5 (10)	C5—C14—H14B	109.5
C7—C2—C3	116.44 (15)	H14A—C14—H14B	109.5
C7—C2—C1	124.54 (14)	C5—C14—H14C	109.5
C3—C2—C1	118.98 (14)	H14A—C14—H14C	109.5
C2—C3—C4	121.38 (16)	H14B—C14—H14C	109.5
C2—C3—H3	119.3	C5—C14—H14D	109.5
C4—C3—H3	119.3	H14A—C14—H14D	141.1
C5—C4—C3	122.37 (17)	H14B—C14—H14D	56.3
C5—C4—H4	118.8	H14C—C14—H14D	56.3
C3—C4—H4	118.8	C5—C14—H14E	109.5
C4—C5—C6	115.88 (16)	H14A—C14—H14E	56.3
C4—C5—C14	122.41 (17)	H14B—C14—H14E	141.1
C6—C5—C14	121.70 (17)	H14C—C14—H14E	56.3
C5—C6—C7	122.67 (16)	H14D—C14—H14E	109.5
C5—C6—H6	118.7	C5—C14—H14F	109.5
C7—C6—H6	118.7	H14A—C14—H14F	56.3
C2—C7—C6	121.27 (15)	H14B—C14—H14F	56.3
C2—C7—H7	119.4	H14C—C14—H14F	141.1
C6—C7—H7	119.4	H14D—C14—H14F	109.5
C9—C8—C13	122.57 (16)	H14E—C14—H14F	109.5
C9—C8—N1	118.78 (16)	C9—C15—H15A	109.5
C13—C8—N1	118.63 (17)	C9—C15—H15B	109.5
C10—C9—C8	117.55 (18)	H15A—C15—H15B	109.5
C10—C9—C15	120.28 (19)	C9—C15—H15C	109.5
C8—C9—C15	122.17 (16)	H15A—C15—H15C	109.5
C11—C10—C9	121.1 (2)	H15B—C15—H15C	109.5
C11—C10—H10	119.4	C13—C16—H16A	109.5
C9—C10—H10	119.4	C13—C16—H16B	109.5
C12—C11—C10	120.47 (19)	H16A—C16—H16B	109.5
C12—C11—H11	119.8	C13—C16—H16C	109.5
C10—C11—H11	119.8	H16A—C16—H16C	109.5
C11—C12—C13	121.0 (2)	H16B—C16—H16C	109.5
C11—C12—H12	119.5
O1—C1—N1—C8	1.4 (3)	C1—N1—C8—C9	−79.3 (2)
C2—C1—N1—C8	179.93 (15)	C1—N1—C8—C13	101.84 (18)
O1—C1—C2—C7	177.04 (17)	C13—C8—C9—C10	−1.0 (2)
N1—C1—C2—C7	−1.5 (3)	N1—C8—C9—C10	−179.76 (14)
O1—C1—C2—C3	−0.5 (3)	C13—C8—C9—C15	178.53 (16)
N1—C1—C2—C3	−179.03 (17)	N1—C8—C9—C15	−0.2 (2)
C7—C2—C3—C4	−0.2 (3)	C8—C9—C10—C11	1.0 (3)
C1—C2—C3—C4	177.5 (2)	C15—C9—C10—C11	−178.47 (18)
C2—C3—C4—C5	0.3 (4)	C9—C10—C11—C12	0.1 (3)
C3—C4—C5—C6	−0.3 (3)	C10—C11—C12—C13	−1.4 (3)
C3—C4—C5—C14	−179.3 (2)	C11—C12—C13—C8	1.4 (3)
C4—C5—C6—C7	0.3 (3)	C11—C12—C13—C16	−178.01 (19)
C14—C5—C6—C7	179.3 (2)	C9—C8—C13—C12	−0.2 (2)
C3—C2—C7—C6	0.2 (3)	N1—C8—C13—C12	178.56 (15)
C1—C2—C7—C6	−177.35 (18)	C9—C8—C13—C16	179.20 (15)
C5—C6—C7—C2	−0.3 (3)	N1—C8—C13—C16	−2.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.89 (1)	2.03 (1)	2.8814 (16)	161 (2)
C7—H7···O1i	0.93	2.48	3.385 (2)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.892 (13)	2.025 (14)	2.8814 (16)	160.6 (15)
C7—H7⋯O1i	0.93	2.48	3.385 (2)	165

Symmetry code: (i) .