1-Meth-oxy-2-methyl-propan-2-aminium 2,2,2-trifluoro-acetate.

In the title salt, C(5)H(14)NO(+)·C(2)F(3)O(2) (-), the cation and anion are linked by N-H⋯O and O-H⋯N hydrogen bonds, generating a three-dimensional network.

Related literature

The title compound is an inter­mediate in the synthesis of 1-meth­oxy-N,2-dimethyl­propan-2-amine. For the synthesis of the title compound, see: Maeda et al. (2004 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C5H14NO+·n class="Chemical">C2F3O2 −

M = 217.19

Orthorhombic,

a = 6.6680 (13) Å

b = 8.9900 (18) Å

c = 17.862 (4) Å

V = 1070.7 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 293 K

0.30 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.961, T max = 0.987

1861 measured reflections

1150 independent reflections

784 reflections with I > 2σ(I)

R int = 0.038

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.183

S = 1.01

1150 reflections

121 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810019100/jh2152sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810019100/jh2152Isup2.hkl

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

C5H14NO+·C2F3O2−	F(000) = 456
Mr = 217.19	Dx = 1.347 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 6.6680 (13) Å	θ = 9–12°
b = 8.9900 (18) Å	µ = 0.14 mm−1
c = 17.862 (4) Å	T = 293 K
V = 1070.7 (4) Å3	Block, colourless
Z = 4	0.30 × 0.10 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	784 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.038
graphite	θmax = 25.3°, θmin = 2.3°
ω/2θ scans	h = −7→8
Absorption correction: ψ scan (North et al., 1968)	k = 0→10
Tmin = 0.961, Tmax = 0.987	l = 0→21
1861 measured reflections	3 standard reflections every 200 reflections
1150 independent reflections	intensity decay: 1%

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.183	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.1P)2 + 0.350P] where P = (Fo2 + 2Fc2)/3
1150 reflections	(Δ/σ)max < 0.001
121 parameters	Δρmax = 0.39 e Å−3
2 restraints	Δρmin = −0.27 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
N	0.4436 (6)	0.2188 (5)	0.4225 (2)	0.0507 (10)
H0A	0.4554	0.1919	0.4702	0.076*
H0B	0.3281	0.2667	0.4159	0.076*
H0C	0.5450	0.2784	0.4102	0.076*
O1	0.2833 (6)	−0.0471 (5)	0.4723 (2)	0.0789 (13)
C1	0.1216 (11)	−0.1286 (9)	0.5000 (4)	0.093 (2)
H1A	0.1419	−0.1486	0.5522	0.139*
H1B	0.1112	−0.2209	0.4732	0.139*
H1C	0.0003	−0.0725	0.4935	0.139*
C2	0.2708 (9)	−0.0130 (8)	0.3959 (3)	0.0674 (16)
H2A	0.1465	0.0392	0.3857	0.081*
H2B	0.2719	−0.1040	0.3667	0.081*
C3	0.4477 (8)	0.0837 (6)	0.3739 (3)	0.0557 (12)
C4	0.4273 (10)	0.1332 (8)	0.2930 (3)	0.0755 (18)
H4A	0.2998	0.1808	0.2861	0.113*
H4B	0.4365	0.0482	0.2607	0.113*
H4C	0.5328	0.2020	0.2812	0.113*
C5	0.6472 (9)	0.0065 (9)	0.3891 (4)	0.084 (2)
H5A	0.6533	−0.0230	0.4407	0.126*
H5B	0.7554	0.0737	0.3784	0.126*
H5C	0.6586	−0.0799	0.3578	0.126*
F1	0.5540 (9)	0.0216 (7)	0.7374 (2)	0.139 (2)
F2	0.7402 (6)	−0.0271 (7)	0.6453 (4)	0.159 (3)
F3	0.4744 (7)	−0.1451 (5)	0.6637 (3)	0.1188 (17)
O2	0.5367 (5)	0.1809 (4)	0.5773 (2)	0.0642 (10)
O3	0.2549 (5)	0.1057 (5)	0.6350 (2)	0.0685 (11)
C6	0.5543 (12)	−0.0119 (9)	0.6655 (4)	0.088
C7	0.4376 (8)	0.1040 (6)	0.6208 (3)	0.0526 (12)

	U11	U22	U33	U12	U13	U23
N	0.0321 (18)	0.067 (2)	0.053 (2)	−0.004 (2)	−0.0039 (18)	0.008 (2)
O1	0.058 (2)	0.095 (3)	0.084 (3)	−0.028 (2)	−0.0068 (19)	0.018 (2)
C1	0.068 (4)	0.104 (5)	0.106 (4)	−0.029 (4)	0.003 (4)	0.024 (5)
C2	0.053 (3)	0.069 (4)	0.080 (4)	−0.011 (3)	−0.006 (3)	−0.009 (3)
C3	0.039 (2)	0.067 (3)	0.062 (3)	0.001 (3)	0.004 (2)	−0.004 (3)
C4	0.069 (4)	0.105 (4)	0.053 (3)	0.001 (4)	0.008 (3)	−0.011 (3)
C5	0.052 (3)	0.086 (5)	0.114 (5)	0.018 (4)	0.017 (3)	0.004 (4)
F1	0.149 (4)	0.191 (5)	0.078 (3)	0.032 (5)	−0.040 (3)	0.025 (3)
F2	0.048 (2)	0.199 (6)	0.230 (6)	0.051 (3)	0.044 (3)	0.126 (5)
F3	0.112 (4)	0.077 (2)	0.167 (4)	0.017 (3)	0.007 (3)	0.035 (3)
O2	0.0486 (19)	0.088 (3)	0.056 (2)	−0.018 (2)	−0.0095 (17)	0.021 (2)
O3	0.0305 (18)	0.090 (3)	0.085 (3)	0.0088 (19)	0.0031 (16)	0.021 (2)
C6	0.088	0.088	0.088	0.000	0.000	0.000
C7	0.049 (3)	0.060 (3)	0.049 (3)	0.002 (3)	−0.003 (2)	0.010 (3)

N—C3	1.493 (7)	C3—C5	1.525 (8)
N—H0A	0.8900	C4—H4A	0.9600
N—H0B	0.8900	C4—H4B	0.9600
N—H0C	0.8900	C4—H4C	0.9600
O1—C1	1.394 (7)	C5—H5A	0.9600
O1—C2	1.402 (7)	C5—H5B	0.9600
C1—H1A	0.9600	C5—H5C	0.9600
C1—H1B	0.9600	F1—C6	1.319 (8)
C1—H1C	0.9600	F2—C6	1.298 (9)
C2—C3	1.517 (8)	F3—C6	1.311 (9)
C2—H2A	0.9700	O2—C7	1.232 (6)
C2—H2B	0.9700	O3—C7	1.244 (6)
C3—C4	1.518 (8)	C6—C7	1.526 (9)
C3—N—H0A	109.5	C2—C3—C5	111.8 (4)
C3—N—H0B	109.5	C4—C3—C5	112.4 (5)
H0A—N—H0B	109.5	C3—C4—H4A	109.5
C3—N—H0C	109.5	C3—C4—H4B	109.5
H0A—N—H0C	109.5	H4A—C4—H4B	109.5
H0B—N—H0C	109.5	C3—C4—H4C	109.5
C1—O1—C2	114.4 (5)	H4A—C4—H4C	109.5
O1—C1—H1A	109.5	H4B—C4—H4C	109.5
O1—C1—H1B	109.5	C3—C5—H5A	109.5
H1A—C1—H1B	109.5	C3—C5—H5B	109.5
O1—C1—H1C	109.5	H5A—C5—H5B	109.5
H1A—C1—H1C	109.5	C3—C5—H5C	109.5
H1B—C1—H1C	109.5	H5A—C5—H5C	109.5
O1—C2—C3	109.3 (4)	H5B—C5—H5C	109.5
O1—C2—H2A	109.8	F2—C6—F3	106.6 (7)
C3—C2—H2A	109.8	F2—C6—F1	107.2 (7)
O1—C2—H2B	109.8	F3—C6—F1	103.4 (7)
C3—C2—H2B	109.8	F2—C6—C7	114.4 (6)
H2A—C2—H2B	108.3	F3—C6—C7	113.8 (6)
N—C3—C2	107.6 (4)	F1—C6—C7	110.6 (6)
N—C3—C4	108.2 (5)	O2—C7—O3	130.3 (5)
C2—C3—C4	110.2 (5)	O2—C7—C6	116.1 (5)
N—C3—C5	106.4 (5)	O3—C7—C6	113.6 (5)
C1—O1—C2—C3	176.4 (5)	F3—C6—C7—O2	−130.9 (6)
O1—C2—C3—N	−57.2 (6)	F1—C6—C7—O2	113.3 (7)
O1—C2—C3—C4	−175.0 (5)	F2—C6—C7—O3	172.5 (7)
O1—C2—C3—C5	59.3 (6)	F3—C6—C7—O3	49.6 (8)
F2—C6—C7—O2	−8.0 (9)	F1—C6—C7—O3	−66.3 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N—H0A···O1	0.89	2.44	2.766 (6)	102
N—H0A···O2	0.89	1.99	2.854 (5)	163
N—H0B···O2i	0.89	2.00	2.859 (5)	161
N—H0C···O3ii	0.89	1.92	2.802 (6)	169
C5—H5A···O1	0.96	2.54	2.886 (8)	101

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H0A⋯O2	0.89	1.99	2.854 (5)	163
N—H0B⋯O2i	0.89	2.00	2.859 (5)	161
N—H0C⋯O3ii	0.89	1.92	2.802 (6)	169

Symmetry codes: (i) ; (ii) .