(2-Decan-amido-eth-yl)dimethyl-amine N-oxide.

In the title compound, C(14)H(30)N(2)O(2), the almost planar nonyl chains are fully extended: the N-C-C-N torsion angle of -161.95 (8)° indicates an anti conformation. The crystal structure features N-H⋯O hydrogen bonds and C-H⋯O inter-actions.

Related literature

For the bond lengths and angles of nonyl chains, see: Low et al. (1999 ▶); Kato & Ikemori (2003 ▶); Ulrich et al. (1990 ▶). For related structures containing the amide group, see: Belicchi-Ferrari et al. (2007 ▶); Jeffrey & Maluszynska (1989 ▶). For N—O bond lengths, see: Katrusiak et al. (1987 ▶); Kemmitt et al. (2002 ▶); Maia et al. (1984 ▶); Boese et al. (1999 ▶); Palatinus & Damay (2009 ▶). For a related structure, see: Sauer et al. (2003 ▶). For the synthesis, see: Piłakowska-Pietras et al. (2008 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶); Rospenk et al. (1989 ▶).

Experimental

Crystal data

C14H30N2O2

M = 258.40

Triclinic,

a = 5.378 (2) Å

b = 8.113 (4) Å

c = 17.801 (5) Å

α = 79.55 (4)°

β = 86.38 (3)°

γ = 86.36 (4)°

V = 761.2 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.23 × 0.19 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur Sapphire2 diffractometer

10305 measured reflections

3149 independent reflections

2746 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.094

S = 1.06

3149 reflections

169 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810022270/ds2034sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022270/ds2034Isup2.hkl

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

C14H30N2O2	Z = 2
Mr = 258.40	F(000) = 288
Triclinic, P1	Dx = 1.127 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.378 (2) Å	Cell parameters from 9030 reflections
b = 8.113 (4) Å	θ = 3–36°
c = 17.801 (5) Å	µ = 0.08 mm−1
α = 79.55 (4)°	T = 100 K
β = 86.38 (3)°	Block, colorless
γ = 86.36 (4)°	0.23 × 0.19 × 0.08 mm
V = 761.2 (5) Å3

Oxford Diffraction Xcalibur Sapphire2 (large Be window) diffractometer	2746 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.018
graphite	θmax = 26.5°, θmin = 3.0°
ω scans	h = −6→6
10305 measured reflections	k = −8→10
3149 independent reflections	l = −22→22

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0535P)2 + 0.1328P] where P = (Fo2 + 2Fc2)/3
3149 reflections	(Δ/σ)max = 0.001
169 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.15 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
O1	−0.14655 (12)	0.29531 (8)	0.63607 (4)	0.01841 (17)
O2	0.61547 (12)	0.19768 (8)	0.42458 (4)	0.01908 (17)
N1	−0.00050 (14)	0.15787 (9)	0.61997 (4)	0.01399 (18)
N2	0.31670 (14)	0.39834 (10)	0.44253 (4)	0.01548 (18)
C1	0.11161 (17)	0.19110 (11)	0.53929 (5)	0.0149 (2)
H1A	−0.0245	0.2133	0.5033	0.018*
H1B	0.2102	0.0895	0.5291	0.018*
C2	0.27914 (17)	0.33925 (11)	0.52434 (5)	0.01533 (19)
H2A	0.2015	0.4313	0.5490	0.018*
H2B	0.4422	0.3047	0.5468	0.018*
C3	0.48478 (16)	0.32380 (11)	0.39906 (5)	0.01460 (19)
C4	0.49927 (17)	0.40400 (12)	0.31534 (5)	0.0169 (2)
H4A	0.4090	0.5154	0.3094	0.020*
H4B	0.4129	0.3340	0.2861	0.020*
C5	0.76504 (17)	0.42604 (12)	0.28085 (5)	0.0175 (2)
H5A	0.8587	0.4857	0.3128	0.021*
H5B	0.8504	0.3144	0.2805	0.021*
C6	0.76453 (18)	0.52507 (12)	0.19949 (5)	0.0187 (2)
H6A	0.6695	0.6335	0.2000	0.022*
H6B	0.6765	0.4620	0.1675	0.022*
C7	1.02383 (18)	0.55974 (13)	0.16275 (6)	0.0210 (2)
H7A	1.1189	0.4515	0.1617	0.025*
H7B	1.1125	0.6227	0.1946	0.025*
C8	1.01841 (18)	0.65973 (13)	0.08150 (5)	0.0217 (2)
H8A	0.9321	0.5957	0.0496	0.026*
H8B	0.9202	0.7668	0.0825	0.026*
C9	1.27600 (19)	0.69820 (13)	0.04450 (6)	0.0218 (2)
H9A	1.3607	0.7643	0.0759	0.026*
H9B	1.3753	0.5911	0.0446	0.026*
C10	1.27329 (19)	0.79467 (13)	−0.03721 (6)	0.0218 (2)
H10A	1.1736	0.9017	−0.0377	0.026*
H10B	1.1907	0.7284	−0.0690	0.026*
C11	1.5337 (2)	0.83259 (13)	−0.07251 (6)	0.0246 (2)
H11A	1.6154	0.8998	−0.0409	0.030*
H11B	1.6338	0.7256	−0.0714	0.030*
C12	1.5335 (2)	0.92734 (15)	−0.15446 (6)	0.0327 (3)
H12A	1.7055	0.9478	−0.1738	0.049*
H12B	1.4383	1.0348	−0.1559	0.049*
H12C	1.4566	0.8605	−0.1865	0.049*
C13	0.19656 (17)	0.11555 (12)	0.67652 (5)	0.0181 (2)
H13A	0.1186	0.0964	0.7284	0.027*
H13B	0.3077	0.2087	0.6709	0.027*
H13C	0.2931	0.0138	0.6675	0.027*
C14	−0.15989 (17)	0.01185 (11)	0.62702 (5)	0.0180 (2)
H14A	−0.2401	−0.0103	0.6786	0.027*
H14B	−0.0565	−0.0872	0.6179	0.027*
H14C	−0.2881	0.0369	0.5892	0.027*
H2	0.246 (2)	0.4950 (17)	0.4221 (7)	0.027 (3)*

	U11	U22	U33	U12	U13	U23
O1	0.0201 (3)	0.0152 (3)	0.0181 (3)	0.0071 (3)	0.0033 (3)	−0.0022 (3)
O2	0.0176 (3)	0.0169 (3)	0.0207 (4)	0.0037 (3)	0.0009 (3)	−0.0003 (3)
N1	0.0136 (4)	0.0137 (4)	0.0135 (4)	0.0021 (3)	0.0010 (3)	−0.0008 (3)
N2	0.0151 (4)	0.0140 (4)	0.0154 (4)	0.0010 (3)	0.0015 (3)	0.0013 (3)
C1	0.0156 (4)	0.0163 (4)	0.0119 (4)	−0.0004 (3)	0.0012 (3)	−0.0013 (3)
C2	0.0149 (4)	0.0163 (4)	0.0139 (4)	−0.0006 (3)	0.0010 (3)	−0.0007 (3)
C3	0.0124 (4)	0.0136 (4)	0.0174 (4)	−0.0024 (3)	0.0002 (3)	−0.0017 (3)
C4	0.0153 (4)	0.0182 (5)	0.0160 (5)	0.0009 (3)	0.0010 (3)	−0.0015 (3)
C5	0.0158 (4)	0.0186 (5)	0.0163 (5)	0.0011 (3)	0.0026 (3)	−0.0002 (4)
C6	0.0180 (5)	0.0206 (5)	0.0159 (5)	−0.0002 (4)	0.0019 (4)	−0.0005 (4)
C7	0.0189 (5)	0.0248 (5)	0.0170 (5)	−0.0003 (4)	0.0024 (4)	0.0012 (4)
C8	0.0209 (5)	0.0260 (5)	0.0161 (5)	−0.0018 (4)	0.0018 (4)	0.0013 (4)
C9	0.0217 (5)	0.0244 (5)	0.0171 (5)	−0.0020 (4)	0.0021 (4)	0.0012 (4)
C10	0.0239 (5)	0.0236 (5)	0.0165 (5)	−0.0029 (4)	0.0015 (4)	0.0001 (4)
C11	0.0267 (5)	0.0266 (5)	0.0183 (5)	−0.0032 (4)	0.0038 (4)	0.0007 (4)
C12	0.0408 (7)	0.0354 (6)	0.0193 (5)	−0.0086 (5)	0.0057 (5)	0.0016 (4)
C13	0.0177 (4)	0.0208 (5)	0.0145 (4)	0.0018 (4)	−0.0030 (3)	0.0001 (4)
C14	0.0157 (4)	0.0168 (5)	0.0201 (5)	−0.0021 (3)	0.0027 (4)	−0.0008 (4)

O1—N1	1.385 (2)	C5—H5A	0.9900
O2—C3	1.237 (2)	C5—H5B	0.9900
N1—C1	1.506 (2)	C6—H6A	0.9900
N1—C13	1.489 (2)	C6—H6B	0.9900
N1—C14	1.489 (2)	C7—H7A	0.9900
N2—C2	1.454 (2)	C7—H7B	0.9900
N2—C3	1.340 (2)	C8—H8A	0.9900
N2—H2	0.87 (2)	C8—H8B	0.9900
C1—C2	1.523 (2)	C9—H9A	0.9900
C3—C4	1.514 (2)	C9—H9B	0.9900
C4—C5	1.528 (2)	C10—H10A	0.9900
C5—C6	1.523 (2)	C10—H10B	0.9900
C6—C7	1.524 (2)	C11—H11A	0.9900
C7—C8	1.525 (2)	C11—H11B	0.9900
C8—C9	1.522 (2)	C12—H12A	0.9800
C9—C10	1.522 (2)	C12—H12B	0.9800
C10—C11	1.524 (2)	C12—H12C	0.9800
C11—C12	1.520 (2)	C13—H13A	0.9800
C1—H1A	0.9900	C13—H13B	0.9800
C1—H1B	0.9900	C13—H13C	0.9800
C2—H2A	0.9900	C14—H14A	0.9800
C2—H2B	0.9900	C14—H14B	0.9800
C4—H4A	0.9900	C14—H14C	0.9800
C4—H4B	0.9900
O1—N1—C1	111.04 (7)	C7—C6—H6B	109.00
O1—N1—C13	109.25 (7)	H6A—C6—H6B	108.00
O1—N1—C14	108.99 (7)	C6—C7—H7A	109.00
C1—N1—C13	111.29 (7)	C6—C7—H7B	109.00
C1—N1—C14	107.63 (7)	C8—C7—H7A	109.00
C13—N1—C14	108.58 (8)	C8—C7—H7B	109.00
C2—N2—C3	122.22 (8)	H7A—C7—H7B	108.00
C3—N2—H2	117.9 (8)	C7—C8—H8A	109.00
C2—N2—H2	119.1 (8)	C7—C8—H8B	109.00
N1—C1—C2	112.89 (8)	C9—C8—H8A	109.00
N2—C2—C1	110.07 (8)	C9—C8—H8B	109.00
O2—C3—N2	123.01 (9)	H8A—C8—H8B	108.00
O2—C3—C4	122.25 (9)	C8—C9—H9A	109.00
N2—C3—C4	114.73 (8)	C8—C9—H9B	109.00
C3—C4—C5	114.08 (8)	C10—C9—H9A	109.00
C4—C5—C6	110.99 (8)	C10—C9—H9B	109.00
C5—C6—C7	113.98 (8)	H9A—C9—H9B	108.00
C6—C7—C8	112.97 (8)	C9—C10—H10A	109.00
C7—C8—C9	113.64 (8)	C9—C10—H10B	109.00
C8—C9—C10	114.14 (9)	C11—C10—H10A	109.00
C9—C10—C11	112.91 (8)	C11—C10—H10B	109.00
C10—C11—C12	113.41 (9)	H10A—C10—H10B	108.00
N1—C1—H1A	109.00	C10—C11—H11A	109.00
N1—C1—H1B	109.00	C10—C11—H11B	109.00
C2—C1—H1A	109.00	C12—C11—H11A	109.00
C2—C1—H1B	109.00	C12—C11—H11B	109.00
H1A—C1—H1B	108.00	H11A—C11—H11B	108.00
N2—C2—H2A	110.00	C11—C12—H12A	109.00
N2—C2—H2B	110.00	C11—C12—H12B	109.00
C1—C2—H2A	110.00	C11—C12—H12C	109.00
C1—C2—H2B	110.00	H12A—C12—H12B	110.00
H2A—C2—H2B	108.00	H12A—C12—H12C	109.00
C3—C4—H4A	109.00	H12B—C12—H12C	109.00
C3—C4—H4B	109.00	N1—C13—H13A	109.00
C5—C4—H4A	109.00	N1—C13—H13B	109.00
C5—C4—H4B	109.00	N1—C13—H13C	110.00
H4A—C4—H4B	108.00	H13A—C13—H13B	109.00
C4—C5—H5A	109.00	H13A—C13—H13C	109.00
C4—C5—H5B	109.00	H13B—C13—H13C	109.00
C6—C5—H5A	109.00	N1—C14—H14A	109.00
C6—C5—H5B	109.00	N1—C14—H14B	109.00
H5A—C5—H5B	108.00	N1—C14—H14C	109.00
C5—C6—H6A	109.00	H14A—C14—H14B	110.00
C5—C6—H6B	109.00	H14A—C14—H14C	109.00
C7—C6—H6A	109.00	H14B—C14—H14C	109.00
O1—N1—C1—C2	60.52 (9)	N2—C3—C4—C5	135.19 (9)
C13—N1—C1—C2	−61.41 (9)	C3—C4—C5—C6	−173.49 (8)
C14—N1—C1—C2	179.74 (8)	C4—C5—C6—C7	177.04 (8)
C3—N2—C2—C1	−81.38 (10)	C5—C6—C7—C8	−179.74 (9)
C2—N2—C3—O2	1.92 (13)	C6—C7—C8—C9	178.94 (9)
C2—N2—C3—C4	−179.36 (8)	C7—C8—C9—C10	178.76 (9)
N1—C1—C2—N2	−161.95 (8)	C8—C9—C10—C11	179.52 (9)
O2—C3—C4—C5	−46.08 (12)	C9—C10—C11—C12	179.38 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.87 (2)	1.89 (2)	2.753 (2)	168.9 (2)
C1—H1A···O2ii	0.99	2.48	3.453 (2)	166
C1—H1B···O2iii	0.99	2.47	3.363 (2)	150
C4—H4A···O1i	0.99	2.32	3.204 (2)	148
C13—H13C···O2iii	0.98	2.58	3.438 (2)	146
C14—H14B···O2iii	0.98	2.60	3.449 (2)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.87 (2)	1.89 (2)	2.753 (2)	168.9 (2)
C1—H1A⋯O2ii	0.99	2.48	3.453 (2)	166
C1—H1B⋯O2iii	0.99	2.47	3.363 (2)	150
C4—H4A⋯O1i	0.99	2.32	3.204 (2)	148
C13—H13C⋯O2iii	0.98	2.58	3.438 (2)	146
C14—H14B⋯O2iii	0.98	2.60	3.449 (2)	145

Symmetry codes: (i) ; (ii) ; (iii) .