N-Ethyl-2,2-dimethyl-N-(3-methyl-phen-yl)propanamide.

In the title compound, C14H21NO, the conformation across the N-C(O) bond is syn-periplanar, the C-N-C-C torsion being -5.9 (5)°. The atoms of the ethyl group attached to the N atom are disordered over two sets of sites with occupancy ratios of 0.65 (2):0.35 (2) (CH2) and 0.689 (14):0.311 (14) (CH3)are linked by very weak C-H⋯O inter-actions forming C(8) chains along [001]. C-H⋯π inter-actions link the mol-ecules along the c-axis direction.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the biological activity of amides, see: Manojkumar et al. (2013a ▶,b ▶). Amide groups can provide structural rigidity to mol­ecules, see: Sreenivasa et al. (2013 ▶).

Experimental

Crystal data

C14H21NO

M = 219.32

Monoclinic,

a = 7.631 (4) Å

b = 10.878 (7) Å

c = 8.350 (3) Å

β = 105.60 (2)°

V = 667.6 (6) Å3

Z = 2

Cu Kα radiation

μ = 0.52 mm−1

T = 294 K

0.22 × 0.20 × 0.16 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.893, T max = 0.921

3786 measured reflections

2016 independent reflections

1883 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.160

S = 1.06

2016 reflections

172 parameters

55 restraints

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814001718/hg5371sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814001718/hg5371Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814001718/hg5371Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C14H21NO	Prism
Mr = 219.32	Dx = 1.091 Mg m−3
Monoclinic, P21	Melting point: 492 K
Hall symbol: P 2yb	Cu Kα radiation, λ = 1.54178 Å
a = 7.631 (4) Å	Cell parameters from 172 reflections
b = 10.878 (7) Å	θ = 5.5–65.5°
c = 8.350 (3) Å	µ = 0.52 mm−1
β = 105.60 (2)°	T = 294 K
V = 667.6 (6) Å3	Prism, yellow
Z = 2	0.22 × 0.20 × 0.16 mm
F(000) = 240

Bruker APEXII diffractometer	1883 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
Graphite monochromator	θmax = 65.5°, θmin = 5.5°
phi and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→12
Tmin = 0.893, Tmax = 0.921	l = −9→9
3786 measured reflections	1012 standard reflections every 2 reflections
2016 independent reflections	intensity decay: 1%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057	H-atom parameters constrained
wR(F2) = 0.160	w = 1/[σ2(Fo2) + (0.093P)2 + 0.1495P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2016 reflections	Δρmax = 0.34 e Å−3
172 parameters	Δρmin = −0.16 e Å−3
55 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraints	Extinction coefficient: 0.018 (4)
Primary atom site location: structure-invariant direct methods

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)
O	0.2284 (2)	0.7636 (3)	0.6964 (2)	0.0725 (7)
N	0.4145 (3)	0.7530 (3)	0.9461 (2)	0.0670 (8)
C11	0.5373 (3)	0.7418 (3)	0.6942 (3)	0.0489 (6)
C6	0.8300 (4)	0.8185 (3)	1.2843 (3)	0.0494 (6)
C10	0.3855 (3)	0.7522 (3)	0.7806 (3)	0.0452 (6)
C4	0.5820 (3)	0.7342 (3)	1.0730 (3)	0.0487 (7)
C5	0.6765 (4)	0.8340 (3)	1.1519 (3)	0.0520 (7)
H5	0.6374	0.9128	1.1164	0.062*
C3	0.6371 (4)	0.6191 (3)	1.1298 (3)	0.0586 (8)
H3	0.5716	0.5510	1.0789	0.070*
C2	0.7875 (4)	0.6028 (3)	1.2607 (4)	0.0602 (8)
H2	0.8249	0.5239	1.2975	0.072*
C1	0.8829 (4)	0.7029 (3)	1.3376 (3)	0.0520 (7)
H1	0.9848	0.6916	1.4271	0.062*
C7	0.9325 (5)	0.9283 (4)	1.3690 (5)	0.0834 (11)
H7A	0.9820	0.9109	1.4851	0.125*
H7B	0.8515	0.9974	1.3563	0.125*
H7C	1.0295	0.9472	1.3200	0.125*
C14	0.4518 (6)	0.7552 (8)	0.5111 (5)	0.129 (2)
H14A	0.5454	0.7608	0.4542	0.193*
H14B	0.3787	0.8283	0.4908	0.193*
H14C	0.3766	0.6849	0.4710	0.193*
C13	0.6307 (11)	0.6209 (5)	0.7262 (9)	0.136 (3)
H13A	0.5417	0.5564	0.7079	0.205*
H13B	0.7044	0.6178	0.8392	0.205*
H13C	0.7066	0.6103	0.6523	0.205*
C12	0.6785 (8)	0.8393 (6)	0.7487 (7)	0.135 (3)
H12A	0.7324	0.8325	0.8663	0.202*
H12B	0.6230	0.9187	0.7237	0.202*
H12C	0.7708	0.8293	0.6910	0.202*
C8A	0.2598 (9)	0.7879 (9)	1.0135 (7)	0.052 (2)	0.65 (2)
H8A1	0.1744	0.8395	0.9348	0.063*	0.65 (2)
H8A2	0.3035	0.8329	1.1169	0.063*	0.65 (2)
C8B	0.2459 (15)	0.7104 (19)	1.0046 (14)	0.059 (4)	0.35 (2)
H8B1	0.1529	0.6742	0.9142	0.070*	0.35 (2)
H8B2	0.2801	0.6522	1.0958	0.070*	0.35 (2)
C9A	0.1691 (10)	0.6700 (7)	1.0428 (8)	0.087 (2)	0.689 (14)
H9A1	0.1289	0.6256	0.9400	0.131*	0.689 (14)
H9A2	0.0664	0.6887	1.0843	0.131*	0.689 (14)
H9A3	0.2542	0.6207	1.1226	0.131*	0.689 (14)
C9B	0.1877 (19)	0.8243 (14)	1.0567 (15)	0.071 (4)	0.311 (14)
H9B1	0.2883	0.8636	1.1337	0.107*	0.311 (14)
H9B2	0.0925	0.8096	1.1096	0.107*	0.311 (14)
H9B3	0.1429	0.8765	0.9617	0.107*	0.311 (14)

	U11	U22	U33	U12	U13	U23
O	0.0395 (10)	0.130 (2)	0.0405 (9)	0.0096 (12)	−0.0029 (8)	−0.0003 (11)
N	0.0294 (10)	0.136 (2)	0.0338 (10)	0.0065 (14)	0.0055 (8)	0.0032 (14)
C11	0.0481 (13)	0.0608 (15)	0.0394 (12)	0.0028 (13)	0.0147 (10)	0.0013 (11)
C6	0.0429 (14)	0.0613 (17)	0.0417 (12)	−0.0053 (13)	0.0072 (10)	0.0004 (12)
C10	0.0375 (12)	0.0603 (14)	0.0343 (11)	−0.0002 (12)	0.0038 (9)	−0.0004 (11)
C4	0.0336 (12)	0.0806 (19)	0.0298 (10)	0.0034 (13)	0.0051 (9)	0.0036 (12)
C5	0.0456 (15)	0.0645 (17)	0.0427 (13)	0.0073 (13)	0.0063 (11)	0.0077 (12)
C3	0.0559 (17)	0.0689 (19)	0.0469 (15)	−0.0075 (15)	0.0067 (13)	−0.0085 (13)
C2	0.0631 (18)	0.0565 (17)	0.0542 (15)	0.0061 (14)	0.0040 (14)	0.0069 (13)
C1	0.0417 (15)	0.0677 (18)	0.0404 (12)	0.0050 (13)	0.0003 (11)	0.0069 (12)
C7	0.079 (2)	0.073 (2)	0.083 (3)	−0.0182 (19)	−0.0049 (19)	−0.0069 (18)
C14	0.086 (3)	0.254 (7)	0.0529 (18)	0.027 (4)	0.0323 (19)	0.021 (3)
C13	0.189 (6)	0.118 (4)	0.150 (5)	0.083 (4)	0.126 (5)	0.052 (3)
C12	0.134 (4)	0.178 (5)	0.125 (4)	−0.087 (4)	0.091 (4)	−0.062 (4)
C8A	0.038 (3)	0.075 (5)	0.045 (2)	0.006 (3)	0.0115 (19)	−0.008 (3)
C8B	0.037 (5)	0.083 (10)	0.054 (5)	−0.014 (6)	0.009 (4)	0.001 (5)
C9A	0.066 (4)	0.110 (5)	0.101 (4)	−0.013 (3)	0.049 (3)	0.001 (4)
C9B	0.057 (7)	0.095 (8)	0.073 (7)	0.006 (6)	0.035 (5)	0.003 (6)

O—C10	1.222 (3)	C7—H7C	0.9600
N—C10	1.339 (3)	C14—H14A	0.9600
N—C4	1.439 (3)	C14—H14B	0.9600
N—C8A	1.488 (7)	C14—H14C	0.9600
N—C8B	1.564 (12)	C13—H13A	0.9600
C11—C13	1.486 (5)	C13—H13B	0.9600
C11—C12	1.493 (5)	C13—H13C	0.9600
C11—C14	1.499 (5)	C12—H12A	0.9600
C11—C10	1.525 (3)	C12—H12B	0.9600
C6—C1	1.359 (4)	C12—H12C	0.9600
C6—C5	1.388 (4)	C8A—C9A	1.508 (13)
C6—C7	1.497 (5)	C8A—H8A1	0.9700
C4—C3	1.364 (4)	C8A—H8A2	0.9700
C4—C5	1.370 (4)	C8B—C9B	1.42 (3)
C5—H5	0.9300	C8B—H8B1	0.9700
C3—C2	1.367 (4)	C8B—H8B2	0.9700
C3—H3	0.9300	C9A—H9A1	0.9600
C2—C1	1.370 (4)	C9A—H9A2	0.9600
C2—H2	0.9300	C9A—H9A3	0.9600
C1—H1	0.9300	C9B—H9B1	0.9600
C7—H7A	0.9600	C9B—H9B2	0.9600
C7—H7B	0.9600	C9B—H9B3	0.9600
C10—N—C4	128.83 (19)	H7B—C7—H7C	109.5
C10—N—C8A	117.7 (3)	C11—C14—H14A	109.5
C4—N—C8A	113.3 (2)	C11—C14—H14B	109.5
C10—N—C8B	113.5 (5)	H14A—C14—H14B	109.5
C4—N—C8B	111.7 (4)	C11—C14—H14C	109.5
C13—C11—C12	107.6 (5)	H14A—C14—H14C	109.5
C13—C11—C14	109.0 (4)	H14B—C14—H14C	109.5
C12—C11—C14	108.8 (4)	C11—C13—H13A	109.5
C13—C11—C10	111.7 (3)	C11—C13—H13B	109.5
C12—C11—C10	112.4 (3)	H13A—C13—H13B	109.5
C14—C11—C10	107.3 (2)	C11—C13—H13C	109.5
C1—C6—C5	119.1 (3)	H13A—C13—H13C	109.5
C1—C6—C7	120.8 (3)	H13B—C13—H13C	109.5
C5—C6—C7	120.1 (3)	C11—C12—H12A	109.5
O—C10—N	117.2 (2)	C11—C12—H12B	109.5
O—C10—C11	119.2 (2)	H12A—C12—H12B	109.5
N—C10—C11	123.6 (2)	C11—C12—H12C	109.5
C3—C4—C5	119.1 (2)	H12A—C12—H12C	109.5
C3—C4—N	121.1 (3)	H12B—C12—H12C	109.5
C5—C4—N	119.3 (3)	N—C8A—C9A	106.8 (6)
C4—C5—C6	120.6 (3)	N—C8A—H8A1	110.4
C4—C5—H5	119.7	C9A—C8A—H8A1	110.4
C6—C5—H5	119.7	N—C8A—H8A2	110.4
C4—C3—C2	120.7 (3)	C9A—C8A—H8A2	110.4
C4—C3—H3	119.6	H8A1—C8A—H8A2	108.6
C2—C3—H3	119.6	C9B—C8B—N	100.9 (13)
C3—C2—C1	119.9 (3)	C9B—C8B—H8B1	111.6
C3—C2—H2	120.1	N—C8B—H8B1	111.6
C1—C2—H2	120.1	C9B—C8B—H8B2	111.6
C6—C1—C2	120.6 (2)	N—C8B—H8B2	111.6
C6—C1—H1	119.7	H8B1—C8B—H8B2	109.4
C2—C1—H1	119.7	C8A—C9A—H9A1	109.5
C6—C7—H7A	109.5	C8A—C9A—H9A2	109.5
C6—C7—H7B	109.5	H9A1—C9A—H9A2	109.5
H7A—C7—H7B	109.5	C8A—C9A—H9A3	109.5
C6—C7—H7C	109.5	H9A1—C9A—H9A3	109.5
H7A—C7—H7C	109.5	H9A2—C9A—H9A3	109.5
C4—N—C10—O	175.9 (3)	C8B—N—C4—C5	−109.8 (9)
C8A—N—C10—O	−9.8 (6)	C3—C4—C5—C6	2.2 (4)
C8B—N—C10—O	25.7 (9)	N—C4—C5—C6	174.5 (2)
C4—N—C10—C11	−5.9 (5)	C1—C6—C5—C4	−1.7 (4)
C8A—N—C10—C11	168.3 (5)	C7—C6—C5—C4	179.8 (3)
C8B—N—C10—C11	−156.1 (9)	C5—C4—C3—C2	−1.8 (4)
C13—C11—C10—O	−116.5 (5)	N—C4—C3—C2	−174.0 (3)
C12—C11—C10—O	122.5 (4)	C4—C3—C2—C1	0.9 (5)
C14—C11—C10—O	2.9 (5)	C5—C6—C1—C2	0.8 (4)
C13—C11—C10—N	65.3 (5)	C7—C6—C1—C2	179.3 (3)
C12—C11—C10—N	−55.7 (5)	C3—C2—C1—C6	−0.4 (4)
C14—C11—C10—N	−175.2 (4)	C10—N—C8A—C9A	94.8 (5)
C10—N—C4—C3	−88.2 (4)	C4—N—C8A—C9A	−90.0 (5)
C8A—N—C4—C3	97.3 (5)	C8B—N—C8A—C9A	4.1 (8)
C8B—N—C4—C3	62.4 (9)	C10—N—C8B—C9B	−107.2 (7)
C10—N—C4—C5	99.6 (4)	C4—N—C8B—C9B	97.4 (8)
C8A—N—C4—C5	−74.9 (5)	C8A—N—C8B—C9B	−2.2 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Oi	0.93	2.62	3.481 (2)	153
C14—H14A···Cgii	0.96	2.85	3.769 (8)	161

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centoid of the benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Oi	0.93	2.62	3.481 (2)	153
C14—H14A⋯Cg ii	0.96	2.85	3.769 (8)	161

Symmetry codes: (i) ; (ii) .