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

In the title mol-ecule, C(16)H(17)NO, the N-H and C=O groups are in the anti-periplanar conformation that has been observed in related compounds. Furthermore, the conformation of the C=O group with respect to the methyl substituent in the 2-methyl-phenyl ring is syn, as has also been observed in related structures. The amide group makes dihedral angles of 50.3 (3) and 64.6 (3)° with the 2-methyl-phenyl and 2,6-dimethyl-phenyl rings, respectively, while the angle between the planes of the two rings is 14.26 (7)°. The mol-ecules are packed into chains via N-H⋯O hydrogen bonds. An intramolecular C-H⋯O hydrogen bond is also observed.

Related literature

For related literature, see: Gowda et al. (2003 ▶); Gowda, Foro et al. (2008 ▶); Gowda, Tokarčík et al. (2008 ▶).

Experimental

Crystal data

C16H17NO

M = 239.31

Orthorhombic,

a = 11.687 (1) Å

b = 10.0187 (8) Å

c = 22.108 (2) Å

V = 2588.6 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 100 (2) K

0.36 × 0.24 × 0.04 mm

Data collection

Oxford Xcalibur diffractometer with Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.971, T max = 0.999

10773 measured reflections

2624 independent reflections

1864 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.127

S = 1.00

2624 reflections

169 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2004 ▶); 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 ▶) and JANA2000 (Petříček et al., 2000 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXS97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680802309X/fb2099sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802309X/fb2099Isup2.hkl

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

C16H17NO	Dx = 1.228 Mg m−3
Mr = 239.31	Melting point: 409 K
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4403 reflections
a = 11.687 (1) Å	θ = 2.2–28.0º
b = 10.0187 (8) Å	µ = 0.08 mm−1
c = 22.108 (2) Å	T = 100 (2) K
V = 2588.6 (4) Å3	Plate, colourless
Z = 8	0.36 × 0.24 × 0.04 mm
F000 = 1024

Oxford Xcalibur diffractometer with Sapphire CCD detector	2624 independent reflections
Radiation source: fine-focus sealed tube	1864 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.024
T = 100(2) K	θmax = 26.4º
Rotation method data acquisition using ω and φ scans	θmin = 2.8º
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2007)	h = −14→14
Tmin = 0.971, Tmax = 0.999	k = −11→12
10773 measured reflections	l = −27→27

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.127	w = 1/[σ2(Fo2) + (0.0871P)2 + 0.016P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
2624 reflections	Δρmax = 0.27 e Å−3
169 parameters	Δρmin = −0.21 e Å−3
62 constraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

Experimental. CrysAlis RED, Oxford Diffraction Ltd., 2007 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	0.66409 (12)	0.10525 (13)	0.52066 (6)	0.0192 (3)
C2	0.71926 (13)	0.06605 (13)	0.46747 (6)	0.0220 (3)
C3	0.66617 (14)	0.09420 (15)	0.41272 (7)	0.0286 (4)
H3	0.7031	0.0707	0.3760	0.034*
C4	0.56017 (15)	0.15594 (14)	0.41088 (7)	0.0311 (4)
H4	0.5253	0.1753	0.3731	0.037*
C5	0.50550 (13)	0.18914 (14)	0.46372 (7)	0.0275 (4)
H5	0.4319	0.2291	0.4620	0.033*
C6	0.55589 (12)	0.16532 (13)	0.52008 (6)	0.0214 (3)
C7	0.76049 (11)	0.17701 (13)	0.61334 (6)	0.0188 (3)
C8	0.83330 (12)	0.13044 (13)	0.66513 (6)	0.0204 (3)
C9	0.81566 (13)	0.17869 (13)	0.72420 (7)	0.0238 (3)
C10	0.88936 (13)	0.13316 (14)	0.76907 (7)	0.0302 (4)
H10	0.8775	0.1622	0.8095	0.036*
C11	0.97939 (14)	0.04706 (16)	0.75717 (7)	0.0318 (4)
H11	1.0285	0.0188	0.7889	0.038*
C12	0.99719 (13)	0.00269 (15)	0.69892 (8)	0.0298 (4)
H12	1.0596	−0.0549	0.6901	0.036*
C13	0.92333 (13)	0.04273 (14)	0.65328 (7)	0.0244 (3)
H13	0.9342	0.0100	0.6134	0.029*
C14	0.83131 (13)	−0.00795 (15)	0.46972 (7)	0.0277 (4)
H14A	0.8217	−0.0904	0.4930	0.033*
H14B	0.8893	0.0482	0.4891	0.033*
H14C	0.8558	−0.0298	0.4285	0.033*
C15	0.49430 (12)	0.20052 (15)	0.57709 (7)	0.0270 (4)
H15A	0.5274	0.2820	0.5943	0.032*
H15B	0.5019	0.1273	0.6062	0.032*
H15C	0.4131	0.2154	0.5682	0.032*
C16	0.72240 (14)	0.27522 (16)	0.73949 (7)	0.0319 (4)
H16A	0.6542	0.2545	0.7155	0.038*
H16B	0.7479	0.3662	0.7304	0.038*
H16C	0.7040	0.2682	0.7826	0.038*
O1	0.74295 (8)	0.29638 (10)	0.60380 (4)	0.0221 (3)
N1	0.71980 (10)	0.07909 (12)	0.57731 (5)	0.0198 (3)
H1N	0.7370 (13)	−0.0079 (17)	0.5864 (7)	0.024*

	U11	U22	U33	U12	U13	U23
C1	0.0241 (7)	0.0121 (7)	0.0214 (7)	−0.0040 (6)	−0.0027 (6)	0.0008 (5)
C2	0.0294 (8)	0.0141 (7)	0.0226 (8)	−0.0037 (6)	−0.0004 (6)	0.0003 (5)
C3	0.0437 (10)	0.0198 (8)	0.0223 (7)	−0.0024 (7)	−0.0011 (7)	−0.0009 (6)
C4	0.0469 (10)	0.0206 (8)	0.0259 (8)	−0.0016 (8)	−0.0131 (7)	0.0003 (6)
C5	0.0293 (8)	0.0167 (7)	0.0364 (9)	0.0004 (7)	−0.0101 (7)	−0.0005 (6)
C6	0.0247 (7)	0.0128 (7)	0.0266 (8)	−0.0047 (6)	−0.0035 (6)	0.0012 (6)
C7	0.0199 (7)	0.0159 (8)	0.0208 (7)	−0.0020 (6)	0.0058 (6)	0.0001 (6)
C8	0.0243 (7)	0.0141 (7)	0.0228 (8)	−0.0052 (6)	−0.0003 (6)	0.0029 (5)
C9	0.0284 (7)	0.0180 (7)	0.0251 (8)	−0.0050 (6)	−0.0010 (6)	−0.0009 (6)
C10	0.0403 (9)	0.0270 (8)	0.0235 (8)	−0.0038 (7)	−0.0063 (7)	−0.0011 (6)
C11	0.0337 (8)	0.0290 (8)	0.0326 (9)	−0.0019 (7)	−0.0136 (7)	0.0053 (7)
C12	0.0266 (8)	0.0256 (8)	0.0372 (10)	0.0017 (7)	−0.0050 (7)	0.0027 (7)
C13	0.0280 (8)	0.0184 (7)	0.0267 (8)	−0.0009 (7)	−0.0011 (6)	0.0009 (6)
C14	0.0339 (8)	0.0245 (8)	0.0246 (8)	0.0035 (7)	0.0050 (7)	−0.0006 (6)
C15	0.0242 (7)	0.0223 (8)	0.0346 (9)	0.0002 (7)	0.0030 (7)	0.0012 (6)
C16	0.0402 (9)	0.0327 (9)	0.0227 (8)	−0.0003 (8)	−0.0003 (7)	−0.0037 (7)
O1	0.0275 (6)	0.0139 (5)	0.0250 (6)	−0.0004 (4)	0.0020 (4)	0.0014 (4)
N1	0.0260 (6)	0.0142 (6)	0.0193 (6)	0.0019 (5)	−0.0025 (5)	0.0018 (5)

C1—C2	1.397 (2)	C9—C16	1.496 (2)
C1—C6	1.400 (2)	C10—C11	1.386 (2)
C1—N1	1.4357 (17)	C10—H10	0.9500
C2—C3	1.389 (2)	C11—C12	1.378 (2)
C2—C14	1.506 (2)	C11—H11	0.9500
C3—C4	1.385 (2)	C12—C13	1.387 (2)
C3—H3	0.9500	C12—H12	0.9500
C4—C5	1.372 (2)	C13—H13	0.9500
C4—H4	0.9500	C14—H14A	0.9800
C5—C6	1.399 (2)	C14—H14B	0.9800
C5—H5	0.9500	C14—H14C	0.9800
C6—C15	1.494 (2)	C15—H15A	0.9800
C7—O1	1.2316 (17)	C15—H15B	0.9800
C7—N1	1.3502 (18)	C15—H15C	0.9800
C7—C8	1.5009 (19)	C16—H16A	0.9800
C8—C13	1.396 (2)	C16—H16B	0.9800
C8—C9	1.408 (2)	C16—H16C	0.9800
C9—C10	1.391 (2)	N1—H1N	0.917 (17)
C2—C1—C6	121.98 (13)	C12—C11—C10	119.52 (14)
C2—C1—N1	118.27 (12)	C12—C11—H11	120.2
C6—C1—N1	119.73 (12)	C10—C11—H11	120.2
C3—C2—C1	118.04 (13)	C11—C12—C13	119.50 (15)
C3—C2—C14	121.15 (13)	C11—C12—H12	120.2
C1—C2—C14	120.78 (12)	C13—C12—H12	120.2
C4—C3—C2	121.05 (14)	C12—C13—C8	120.98 (14)
C4—C3—H3	119.5	C12—C13—H13	119.5
C2—C3—H3	119.5	C8—C13—H13	119.5
C5—C4—C3	119.97 (14)	C2—C14—H14A	109.5
C5—C4—H4	120.0	C2—C14—H14B	109.5
C3—C4—H4	120.0	H14A—C14—H14B	109.5
C4—C5—C6	121.39 (14)	C2—C14—H14C	109.5
C4—C5—H5	119.3	H14A—C14—H14C	109.5
C6—C5—H5	119.3	H14B—C14—H14C	109.5
C5—C6—C1	117.49 (13)	C6—C15—H15A	109.5
C5—C6—C15	120.57 (13)	C6—C15—H15B	109.5
C1—C6—C15	121.93 (12)	H15A—C15—H15B	109.5
O1—C7—N1	123.09 (13)	C6—C15—H15C	109.5
O1—C7—C8	121.79 (12)	H15A—C15—H15C	109.5
N1—C7—C8	115.08 (12)	H15B—C15—H15C	109.5
C13—C8—C9	120.04 (13)	C9—C16—H16A	109.5
C13—C8—C7	118.69 (12)	C9—C16—H16B	109.5
C9—C8—C7	121.19 (12)	H16A—C16—H16B	109.5
C10—C9—C8	117.28 (14)	C9—C16—H16C	109.5
C10—C9—C16	120.15 (13)	H16A—C16—H16C	109.5
C8—C9—C16	122.57 (13)	H16B—C16—H16C	109.5
C11—C10—C9	122.62 (14)	C7—N1—C1	122.80 (12)
C11—C10—H10	118.7	C7—N1—H1N	118.9 (10)
C9—C10—H10	118.7	C1—N1—H1N	117.7 (10)
C6—C1—C2—C3	3.1 (2)	N1—C7—C8—C9	−132.73 (14)
N1—C1—C2—C3	−178.62 (12)	C13—C8—C9—C10	−1.3 (2)
C6—C1—C2—C14	−175.18 (12)	C7—C8—C9—C10	−178.09 (12)
N1—C1—C2—C14	3.1 (2)	C13—C8—C9—C16	178.58 (14)
C1—C2—C3—C4	−1.8 (2)	C7—C8—C9—C16	1.8 (2)
C14—C2—C3—C4	176.51 (13)	C8—C9—C10—C11	2.0 (2)
C2—C3—C4—C5	−0.6 (2)	C16—C9—C10—C11	−177.92 (14)
C3—C4—C5—C6	1.8 (2)	C9—C10—C11—C12	−0.7 (2)
C4—C5—C6—C1	−0.5 (2)	C10—C11—C12—C13	−1.3 (2)
C4—C5—C6—C15	−179.17 (13)	C11—C12—C13—C8	1.9 (2)
C2—C1—C6—C5	−2.0 (2)	C9—C8—C13—C12	−0.6 (2)
N1—C1—C6—C5	179.75 (12)	C7—C8—C13—C12	176.27 (13)
C2—C1—C6—C15	176.66 (13)	O1—C7—N1—C1	7.7 (2)
N1—C1—C6—C15	−1.6 (2)	C8—C7—N1—C1	−169.99 (11)
O1—C7—C8—C13	−127.30 (14)	C2—C1—N1—C7	112.35 (15)
N1—C7—C8—C13	50.44 (17)	C6—C1—N1—C7	−69.34 (18)
O1—C7—C8—C9	49.54 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.917 (17)	2.012 (17)	2.9248 (15)	173.7 (14)
C15—H15A···O1	0.98	2.53	3.1170 (17)	118

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.917 (17)	2.012 (17)	2.9248 (15)	173.7 (14)
C15—H15A⋯O1	0.98	2.53	3.1170 (17)	118

Symmetry code: (i) .