N-(2,6-Dimethyl-phen-yl)-3-methyl-benzamide.

In the mol-ecular structure of the title compound, C(16)H(17)NO, the N-H and C=O bonds are anti to each other. The two aromatic rings make a dihedral angle of 73.3 (1)°. In the crystal, inter-molecular N-H⋯O hydrogen bonds connect the mol-ecules into C(4) chains running along the c axis.

Related literature

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

Experimental

Crystal data

C16H17NO

M = 239.31

Monoclinic,

a = 12.0715 (4) Å

b = 12.4966 (3) Å

c = 9.7027 (3) Å

β = 112.123 (4)°

V = 1355.92 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 295 K

0.55 × 0.30 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.972, T max = 0.989

11288 measured reflections

1371 independent reflections

1260 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.084

S = 1.08

1371 reflections

169 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.09 e Å−3

Δρmin = −0.11 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/S1600536810011530/bt5228sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011530/bt5228Isup2.hkl

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

C16H17NO	F(000) = 512
Mr = 239.31	Dx = 1.172 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 6791 reflections
a = 12.0715 (4) Å	θ = 2.3–29.5°
b = 12.4966 (3) Å	µ = 0.07 mm−1
c = 9.7027 (3) Å	T = 295 K
β = 112.123 (4)°	Block, colourless
V = 1355.92 (7) Å3	0.55 × 0.30 × 0.18 mm
Z = 4

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	1371 independent reflections
graphite	1260 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1	Rint = 0.030
ω scans	θmax = 26.2°, θmin = 2.4°
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	h = −14→14
Tmin = 0.972, Tmax = 0.989	k = −15→15
11288 measured reflections	l = −12→12

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0513P)2 + 0.1381P] where P = (Fo2 + 2Fc2)/3
1371 reflections	(Δ/σ)max < 0.001
169 parameters	Δρmax = 0.09 e Å−3
3 restraints	Δρmin = −0.11 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	0.78435 (17)	0.48438 (15)	0.42193 (19)	0.0400 (4)
C2	0.67477 (16)	0.55392 (15)	0.3679 (2)	0.0411 (4)
C3	0.58869 (18)	0.53174 (18)	0.2278 (2)	0.0482 (5)
H3	0.6004	0.4745	0.1736	0.058*
C4	0.48627 (19)	0.5928 (2)	0.1676 (2)	0.0558 (5)
C5	0.4723 (2)	0.6792 (2)	0.2490 (3)	0.0622 (6)
H5	0.4047	0.7221	0.2095	0.075*
C6	0.5568 (2)	0.7029 (2)	0.3876 (3)	0.0602 (5)
H6	0.5457	0.7612	0.4407	0.072*
C7	0.65776 (19)	0.64009 (17)	0.4474 (2)	0.0486 (5)
H7	0.7144	0.6556	0.5413	0.058*
C8	0.95159 (17)	0.41695 (16)	0.63591 (19)	0.0422 (4)
C9	1.05908 (18)	0.46294 (17)	0.6440 (2)	0.0494 (5)
C10	1.1631 (2)	0.4041 (2)	0.7137 (3)	0.0621 (6)
H10	1.236	0.4327	0.7202	0.074*
C11	1.1606 (2)	0.3050 (2)	0.7730 (3)	0.0677 (7)
H11	1.2314	0.2674	0.8199	0.081*
C12	1.0537 (3)	0.2613 (2)	0.7630 (3)	0.0631 (6)
H12	1.0529	0.1939	0.8032	0.076*
C13	0.9464 (2)	0.31583 (16)	0.6939 (2)	0.0496 (5)
C14	0.3930 (3)	0.5643 (3)	0.0162 (3)	0.0890 (9)
H14A	0.3383	0.6229	−0.0201	0.134*
H14B	0.35	0.5018	0.0251	0.134*
H14C	0.4318	0.5502	−0.052	0.134*
C15	1.0634 (3)	0.5708 (2)	0.5791 (4)	0.0742 (7)
H15A	1.1447	0.5955	0.6142	0.111*
H15B	1.0159	0.6203	0.609	0.111*
H15C	1.0326	0.5658	0.4726	0.111*
C16	0.8297 (3)	0.2675 (2)	0.6825 (3)	0.0724 (7)
H16A	0.8367	0.191	0.687	0.109*
H16B	0.7684	0.2881	0.5898	0.109*
H16C	0.8091	0.2926	0.7633	0.109*
N1	0.84288 (14)	0.47696 (14)	0.56895 (16)	0.0447 (4)
H1N	0.813 (2)	0.5097 (19)	0.627 (3)	0.054*
O1	0.81747 (13)	0.43660 (12)	0.33310 (16)	0.0518 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0423 (9)	0.0448 (9)	0.0324 (9)	−0.0060 (8)	0.0137 (7)	−0.0005 (8)
C2	0.0397 (9)	0.0481 (10)	0.0340 (9)	−0.0046 (8)	0.0120 (7)	0.0050 (8)
C3	0.0482 (11)	0.0587 (12)	0.0359 (10)	−0.0064 (9)	0.0138 (9)	0.0009 (9)
C4	0.0458 (11)	0.0759 (14)	0.0402 (11)	−0.0028 (10)	0.0099 (9)	0.0115 (10)
C5	0.0512 (12)	0.0728 (15)	0.0604 (14)	0.0135 (11)	0.0185 (11)	0.0195 (12)
C6	0.0631 (13)	0.0576 (12)	0.0598 (14)	0.0085 (11)	0.0229 (11)	0.0032 (10)
C7	0.0487 (10)	0.0525 (11)	0.0408 (10)	−0.0012 (9)	0.0125 (8)	−0.0009 (9)
C8	0.0453 (10)	0.0484 (10)	0.0304 (8)	0.0037 (8)	0.0114 (8)	−0.0028 (7)
C9	0.0473 (11)	0.0570 (12)	0.0418 (11)	−0.0009 (9)	0.0146 (9)	−0.0057 (9)
C10	0.0456 (12)	0.0837 (16)	0.0536 (13)	0.0025 (11)	0.0149 (10)	−0.0075 (12)
C11	0.0613 (15)	0.0842 (18)	0.0515 (12)	0.0281 (13)	0.0141 (11)	0.0041 (12)
C12	0.0868 (17)	0.0527 (13)	0.0523 (13)	0.0181 (12)	0.0291 (12)	0.0080 (10)
C13	0.0605 (11)	0.0510 (11)	0.0376 (9)	0.0016 (10)	0.0187 (9)	−0.0024 (8)
C14	0.0626 (16)	0.133 (3)	0.0529 (15)	0.0034 (17)	0.0006 (13)	0.0060 (16)
C15	0.0653 (15)	0.0700 (15)	0.0866 (19)	−0.0104 (13)	0.0280 (14)	0.0054 (14)
C16	0.0841 (17)	0.0659 (15)	0.0730 (16)	−0.0121 (13)	0.0361 (14)	0.0059 (13)
N1	0.0446 (9)	0.0578 (10)	0.0314 (8)	0.0074 (7)	0.0141 (7)	0.0007 (7)
O1	0.0549 (8)	0.0638 (9)	0.0357 (7)	0.0053 (7)	0.0161 (6)	−0.0030 (6)

C1—O1	1.232 (2)	C9—C15	1.496 (3)
C1—N1	1.336 (2)	C10—C11	1.371 (4)
C1—C2	1.502 (3)	C10—H10	0.93
C2—C7	1.385 (3)	C11—C12	1.370 (4)
C2—C3	1.392 (3)	C11—H11	0.93
C3—C4	1.381 (3)	C12—C13	1.392 (3)
C3—H3	0.93	C12—H12	0.93
C4—C5	1.386 (4)	C13—C16	1.498 (4)
C4—C14	1.518 (3)	C14—H14A	0.96
C5—C6	1.380 (3)	C14—H14B	0.96
C5—H5	0.93	C14—H14C	0.96
C6—C7	1.381 (3)	C15—H15A	0.96
C6—H6	0.93	C15—H15B	0.96
C7—H7	0.93	C15—H15C	0.96
C8—C13	1.394 (3)	C16—H16A	0.96
C8—C9	1.394 (3)	C16—H16B	0.96
C8—N1	1.437 (3)	C16—H16C	0.96
C9—C10	1.391 (3)	N1—H1N	0.875 (17)
O1—C1—N1	122.20 (18)	C12—C11—C10	119.9 (2)
O1—C1—C2	120.72 (16)	C12—C11—H11	120
N1—C1—C2	117.08 (16)	C10—C11—H11	120
C7—C2—C3	119.08 (17)	C11—C12—C13	121.3 (2)
C7—C2—C1	123.44 (16)	C11—C12—H12	119.3
C3—C2—C1	117.45 (17)	C13—C12—H12	119.3
C4—C3—C2	121.5 (2)	C12—C13—C8	117.6 (2)
C4—C3—H3	119.2	C12—C13—C16	121.1 (2)
C2—C3—H3	119.2	C8—C13—C16	121.3 (2)
C3—C4—C5	118.1 (2)	C4—C14—H14A	109.5
C3—C4—C14	120.0 (2)	C4—C14—H14B	109.5
C5—C4—C14	121.9 (2)	H14A—C14—H14B	109.5
C6—C5—C4	121.3 (2)	C4—C14—H14C	109.5
C6—C5—H5	119.4	H14A—C14—H14C	109.5
C4—C5—H5	119.4	H14B—C14—H14C	109.5
C5—C6—C7	119.9 (2)	C9—C15—H15A	109.5
C5—C6—H6	120	C9—C15—H15B	109.5
C7—C6—H6	120	H15A—C15—H15B	109.5
C6—C7—C2	120.05 (19)	C9—C15—H15C	109.5
C6—C7—H7	120	H15A—C15—H15C	109.5
C2—C7—H7	120	H15B—C15—H15C	109.5
C13—C8—C9	122.22 (18)	C13—C16—H16A	109.5
C13—C8—N1	118.92 (18)	C13—C16—H16B	109.5
C9—C8—N1	118.84 (18)	H16A—C16—H16B	109.5
C10—C9—C8	117.4 (2)	C13—C16—H16C	109.5
C10—C9—C15	120.8 (2)	H16A—C16—H16C	109.5
C8—C9—C15	121.80 (19)	H16B—C16—H16C	109.5
C11—C10—C9	121.6 (2)	C1—N1—C8	123.02 (16)
C11—C10—H10	119.2	C1—N1—H1N	118.3 (17)
C9—C10—H10	119.2	C8—N1—H1N	118.7 (17)
O1—C1—C2—C7	−153.25 (19)	C13—C8—C9—C15	179.0 (2)
N1—C1—C2—C7	26.9 (3)	N1—C8—C9—C15	−2.6 (3)
O1—C1—C2—C3	24.4 (3)	C8—C9—C10—C11	−0.3 (3)
N1—C1—C2—C3	−155.44 (17)	C15—C9—C10—C11	−179.7 (2)
C7—C2—C3—C4	−0.8 (3)	C9—C10—C11—C12	0.6 (4)
C1—C2—C3—C4	−178.60 (18)	C10—C11—C12—C13	−0.2 (3)
C2—C3—C4—C5	1.6 (3)	C11—C12—C13—C8	−0.4 (3)
C2—C3—C4—C14	−178.4 (2)	C11—C12—C13—C16	179.6 (2)
C3—C4—C5—C6	−1.2 (3)	C9—C8—C13—C12	0.7 (3)
C14—C4—C5—C6	178.8 (3)	N1—C8—C13—C12	−177.66 (18)
C4—C5—C6—C7	0.1 (3)	C9—C8—C13—C16	−179.3 (2)
C5—C6—C7—C2	0.6 (3)	N1—C8—C13—C16	2.3 (3)
C3—C2—C7—C6	−0.3 (3)	O1—C1—N1—C8	2.8 (3)
C1—C2—C7—C6	177.36 (19)	C2—C1—N1—C8	−177.37 (17)
C13—C8—C9—C10	−0.4 (3)	C13—C8—N1—C1	−101.4 (2)
N1—C8—C9—C10	177.99 (18)	C9—C8—N1—C1	80.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.88 (2)	2.09 (2)	2.902 (2)	154 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.88 (2)	2.09 (2)	2.902 (2)	154 (2)

Symmetry code: (i) .