3-Dodec-yloxy-2-hydr-oxy-N,N,N-trimethyl-propan-1-aminium bromide.

In the title compound, C(18)H(40)NO(2) (+)·Br(-), the ion pairs formed by the hydrogen-bonded bromide anions and organic cations are arranged into thick layers with the alkyl groups directed to the inside and the trimethyl-aminium groups and the bromide anions situated on the layer surface. The long alkyl chain in the cation adopts an all-trans conformation. In the crystal structure, molecules are connected by intermolecular O-H⋯Br hydrogen bonds, forming ionic pairs that are further connected into an extended chain structure via C-H⋯O hydrogen-bonding interactions. The crystal is chiral but nearly 90% of atoms in the unit cell are related by a pseudo-inversion center. The crystal shows racemic twinning with a 0.33:0.67 domain ratio.

Related literature

For related structures, see: Koh et al. (1993 ▶). For applications of 3-alk­oxy-2-hydroxy­propyl-N,N,N-trimethyl­propan-1-amin­ium bromides, see: Yin et al. (2001 ▶); Zhao et al. (1997 ▶).

Experimental

Crystal data

C18H40NO2 +·Br−

M = 382.42

Monoclinic,

a = 6.0476 (11) Å

b = 7.5370 (12) Å

c = 24.870 (2) Å

β = 94.974 (1)°

V = 1129.3 (3) Å3

Z = 2

Mo Kα radiation

μ = 1.83 mm−1

T = 298 K

0.48 × 0.34 × 0.22 mm

Data collection

Bruker SMART diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.474, T max = 0.689

5077 measured reflections

3431 independent reflections

1751 reflections with I > 2σ(I)

R int = 0.081

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.158

S = 1.00

3431 reflections

204 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −0.57 e Å−3

Absolute structure: Flack (1983 ▶), 1274 Friedel pairs

Flack parameter: 0.33 (3)

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; 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/S160053680902635X/gk2214sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902635X/gk2214Isup2.hkl

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

C18H40NO2+·Br−	F(000) = 412
Mr = 382.42	Dx = 1.125 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1870 reflections
a = 6.0476 (11) Å	θ = 2.5–21.7°
b = 7.5370 (12) Å	µ = 1.83 mm−1
c = 24.870 (2) Å	T = 298 K
β = 94.974 (1)°	Block, colorless
V = 1129.3 (3) Å3	0.48 × 0.34 × 0.22 mm
Z = 2

Bruker SMART diffractometer	3431 independent reflections
Radiation source: fine-focus sealed tube	1751 reflections with I > 2σ(I)
graphite	Rint = 0.081
Detector resolution: 0 pixels mm-1	θmax = 25.0°, θmin = 3.2°
φ and ω scans	h = −5→7
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −8→8
Tmin = 0.474, Tmax = 0.689	l = −27→29
5077 measured reflections

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)] = 0.063	H-atom parameters constrained
wR(F2) = 0.158	w = 1/[σ2(Fo2) + (0.045P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.002
3431 reflections	Δρmax = 0.54 e Å−3
204 parameters	Δρmin = −0.57 e Å−3
1 restraint	Absolute structure: Flack (1983), 1274 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.33 (3)

	x	y	z	Uiso*/Ueq
Br1	0.21650 (16)	0.2943 (2)	0.08166 (3)	0.0752 (4)
N1	1.3970 (9)	0.297 (2)	0.91650 (19)	0.0510 (15)
O1	1.7912 (10)	0.1699 (9)	0.8526 (2)	0.0742 (18)
H1	1.7944	0.0836	0.8727	0.089*
O2	1.3595 (12)	0.2556 (13)	0.7440 (2)	0.095 (4)
C1	1.4538 (16)	0.337 (3)	0.8576 (3)	0.105 (8)
H1A	1.3163	0.3636	0.8362	0.126*
H1B	1.5446	0.4429	0.8585	0.126*
C2	1.5697 (15)	0.1972 (15)	0.8294 (3)	0.069 (3)
H2	1.4855	0.0860	0.8283	0.083*
C3	1.5831 (17)	0.274 (3)	0.7705 (3)	0.118 (5)
H3A	1.6280	0.3976	0.7719	0.142*
H3B	1.6888	0.2072	0.7514	0.142*
C4	1.5977 (11)	0.294 (3)	0.9561 (2)	0.063 (2)
H4A	1.6733	0.4062	0.9551	0.095*
H4B	1.6955	0.2010	0.9468	0.095*
H4C	1.5532	0.2743	0.9917	0.095*
C5	1.266 (2)	0.467 (2)	0.9240 (5)	0.070 (5)
H5A	1.3677	0.5631	0.9323	0.105*
H5B	1.1736	0.4515	0.9530	0.105*
H5C	1.1758	0.4931	0.8913	0.105*
C6	1.254 (2)	0.144 (2)	0.9272 (5)	0.081 (5)
H6A	1.2339	0.1394	0.9650	0.122*
H6B	1.3237	0.0367	0.9166	0.122*
H6C	1.1129	0.1574	0.9069	0.122*
C7	1.3494 (19)	0.260 (3)	0.6888 (3)	0.111 (6)
H7A	1.4236	0.1554	0.6767	0.133*
H7B	1.4335	0.3624	0.6784	0.133*
C8	1.1261 (17)	0.269 (3)	0.6594 (3)	0.100 (4)
H8A	1.0373	0.3478	0.6796	0.120*
H8B	1.0610	0.1518	0.6611	0.120*
C9	1.095 (2)	0.329 (3)	0.5998 (4)	0.126 (6)
H9A	1.1088	0.4571	0.5986	0.151*
H9B	1.2151	0.2794	0.5810	0.151*
C10	0.8776 (18)	0.277 (3)	0.5696 (3)	0.111 (4)
H10A	0.7585	0.3264	0.5886	0.133*
H10B	0.8645	0.1488	0.5711	0.133*
C11	0.841 (2)	0.333 (4)	0.5107 (3)	0.130 (7)
H11A	0.8769	0.4584	0.5093	0.156*
H11B	0.9503	0.2710	0.4915	0.156*
C12	0.626 (2)	0.309 (4)	0.4796 (3)	0.132 (5)
H12A	0.5771	0.1909	0.4880	0.158*
H12B	0.5251	0.3907	0.4951	0.158*
C13	0.585 (2)	0.328 (4)	0.4222 (3)	0.139 (8)
H13A	0.6986	0.2589	0.4064	0.167*
H13B	0.6144	0.4513	0.4141	0.167*
C14	0.3699 (19)	0.282 (3)	0.3913 (3)	0.121 (4)
H14A	0.3502	0.1547	0.3947	0.145*
H14B	0.2533	0.3379	0.4097	0.145*
C15	0.3272 (18)	0.326 (4)	0.3326 (3)	0.129 (7)
H15A	0.3428	0.4531	0.3290	0.155*
H15B	0.4445	0.2714	0.3140	0.155*
C16	0.1111 (19)	0.274 (3)	0.3030 (3)	0.120 (5)
H16A	0.0889	0.1491	0.3103	0.143*
H16B	−0.0043	0.3380	0.3197	0.143*
C17	0.069 (2)	0.298 (4)	0.2446 (4)	0.175 (8)
H17A	0.1065	0.4204	0.2370	0.210*
H17B	0.1744	0.2243	0.2279	0.210*
C18	−0.147 (2)	0.265 (4)	0.2162 (4)	0.171 (10)
H18A	−0.1791	0.1400	0.2171	0.257*
H18B	−0.1465	0.3027	0.1794	0.257*
H18C	−0.2589	0.3290	0.2333	0.257*

	U11	U22	U33	U12	U13	U23
Br1	0.0807 (6)	0.0495 (5)	0.0990 (6)	−0.0305 (7)	0.0278 (4)	−0.0123 (8)
N1	0.037 (3)	0.066 (4)	0.050 (3)	0.013 (7)	0.005 (3)	0.003 (8)
O1	0.068 (4)	0.069 (4)	0.086 (4)	0.001 (4)	0.005 (3)	0.006 (3)
O2	0.138 (6)	0.115 (10)	0.030 (3)	0.065 (7)	−0.003 (3)	0.010 (4)
C1	0.065 (6)	0.20 (2)	0.047 (5)	0.023 (11)	−0.010 (5)	−0.007 (9)
C2	0.052 (6)	0.088 (7)	0.067 (7)	0.006 (5)	−0.002 (5)	−0.008 (6)
C3	0.107 (8)	0.210 (16)	0.039 (5)	0.002 (16)	0.006 (5)	0.039 (12)
C4	0.047 (4)	0.085 (6)	0.054 (4)	0.023 (9)	−0.010 (4)	−0.032 (9)
C5	0.072 (9)	0.056 (9)	0.083 (10)	0.046 (7)	0.007 (8)	−0.001 (6)
C6	0.053 (9)	0.070 (10)	0.119 (13)	0.016 (7)	0.001 (8)	−0.037 (9)
C7	0.115 (8)	0.152 (18)	0.066 (6)	0.051 (12)	0.012 (6)	−0.014 (9)
C8	0.124 (9)	0.115 (12)	0.059 (6)	0.018 (11)	0.000 (5)	0.013 (9)
C9	0.157 (11)	0.166 (19)	0.053 (5)	0.010 (14)	0.003 (6)	0.010 (10)
C10	0.133 (9)	0.134 (12)	0.063 (6)	0.020 (14)	−0.006 (6)	−0.016 (11)
C11	0.145 (10)	0.20 (2)	0.046 (6)	−0.005 (14)	0.002 (6)	0.008 (10)
C12	0.162 (10)	0.178 (14)	0.048 (6)	0.035 (18)	−0.025 (6)	−0.010 (14)
C13	0.135 (10)	0.22 (2)	0.053 (6)	−0.046 (16)	−0.019 (6)	0.015 (12)
C14	0.147 (10)	0.152 (12)	0.062 (6)	−0.021 (17)	−0.002 (6)	0.022 (13)
C15	0.120 (9)	0.205 (19)	0.060 (6)	−0.046 (15)	−0.001 (6)	−0.006 (11)
C16	0.141 (10)	0.148 (14)	0.069 (6)	−0.042 (15)	−0.002 (6)	0.004 (12)
C17	0.140 (11)	0.31 (2)	0.069 (7)	0.02 (2)	−0.001 (7)	−0.118 (16)
C18	0.179 (13)	0.26 (3)	0.073 (7)	−0.12 (2)	−0.012 (8)	0.005 (15)

N1—C6	1.48 (2)	C9—C10	1.510 (16)
N1—C4	1.496 (7)	C9—H9A	0.9700
N1—C5	1.524 (18)	C9—H9B	0.9700
N1—C1	1.561 (10)	C10—C11	1.521 (14)
O1—C2	1.426 (10)	C10—H10A	0.9700
O1—H1	0.8200	C10—H10B	0.9700
O2—C7	1.369 (9)	C11—C12	1.463 (16)
O2—C3	1.459 (11)	C11—H11A	0.9700
C1—C2	1.475 (18)	C11—H11B	0.9700
C1—H1A	0.9700	C12—C13	1.435 (11)
C1—H1B	0.9700	C12—H12A	0.9700
C2—C3	1.584 (14)	C12—H12B	0.9700
C2—H2	0.9800	C13—C14	1.495 (15)
C3—H3A	0.9700	C13—H13A	0.9700
C3—H3B	0.9700	C13—H13B	0.9700
C4—H4A	0.9600	C14—C15	1.496 (13)
C4—H4B	0.9600	C14—H14A	0.9700
C4—H4C	0.9600	C14—H14B	0.9700
C5—H5A	0.9600	C15—C16	1.495 (15)
C5—H5B	0.9600	C15—H15A	0.9700
C5—H5C	0.9600	C15—H15B	0.9700
C6—H6A	0.9600	C16—C17	1.465 (13)
C6—H6B	0.9600	C16—H16A	0.9700
C6—H6C	0.9600	C16—H16B	0.9700
C7—C8	1.481 (13)	C17—C18	1.452 (15)
C7—H7A	0.9700	C17—H17A	0.9700
C7—H7B	0.9700	C17—H17B	0.9700
C8—C9	1.544 (13)	C18—H18A	0.9600
C8—H8A	0.9700	C18—H18B	0.9600
C8—H8B	0.9700	C18—H18C	0.9600
C6—N1—C4	109.0 (12)	C8—C9—H9A	108.4
C6—N1—C5	108.4 (6)	C10—C9—H9B	108.4
C4—N1—C5	109.3 (11)	C8—C9—H9B	108.4
C6—N1—C1	119.8 (11)	H9A—C9—H9B	107.5
C4—N1—C1	112.8 (6)	C9—C10—C11	117.0 (13)
C5—N1—C1	96.4 (11)	C9—C10—H10A	108.0
C2—O1—H1	109.5	C11—C10—H10A	108.0
C7—O2—C3	114.2 (8)	C9—C10—H10B	108.0
C2—C1—N1	117.5 (15)	C11—C10—H10B	108.0
C2—C1—H1A	107.9	H10A—C10—H10B	107.3
N1—C1—H1A	107.9	C12—C11—C10	121.6 (13)
C2—C1—H1B	107.9	C12—C11—H11A	106.9
N1—C1—H1B	107.9	C10—C11—H11A	106.9
H1A—C1—H1B	107.2	C12—C11—H11B	106.9
O1—C2—C1	112.3 (8)	C10—C11—H11B	106.9
O1—C2—C3	107.7 (8)	H11A—C11—H11B	106.7
C1—C2—C3	104.2 (12)	C13—C12—C11	125.7 (12)
O1—C2—H2	110.8	C13—C12—H12A	105.9
C1—C2—H2	110.8	C11—C12—H12A	105.9
C3—C2—H2	110.8	C13—C12—H12B	105.9
O2—C3—C2	105.3 (9)	C11—C12—H12B	105.9
O2—C3—H3A	110.7	H12A—C12—H12B	106.2
C2—C3—H3A	110.7	C12—C13—C14	123.8 (12)
O2—C3—H3B	110.7	C12—C13—H13A	106.4
C2—C3—H3B	110.7	C14—C13—H13A	106.4
H3A—C3—H3B	108.8	C12—C13—H13B	106.4
N1—C4—H4A	109.5	C14—C13—H13B	106.4
N1—C4—H4B	109.5	H13A—C13—H13B	106.4
H4A—C4—H4B	109.5	C15—C14—C13	121.3 (12)
N1—C4—H4C	109.5	C15—C14—H14A	107.0
H4A—C4—H4C	109.5	C13—C14—H14A	107.0
H4B—C4—H4C	109.5	C15—C14—H14B	107.0
N1—C5—H5A	109.5	C13—C14—H14B	107.0
N1—C5—H5B	109.5	H14A—C14—H14B	106.8
H5A—C5—H5B	109.5	C16—C15—C14	119.5 (13)
N1—C5—H5C	109.5	C16—C15—H15A	107.5
H5A—C5—H5C	109.5	C14—C15—H15A	107.5
H5B—C5—H5C	109.5	C16—C15—H15B	107.5
N1—C6—H6A	109.5	C14—C15—H15B	107.5
N1—C6—H6B	109.5	H15A—C15—H15B	107.0
H6A—C6—H6B	109.5	C17—C16—C15	121.7 (13)
N1—C6—H6C	109.5	C17—C16—H16A	106.9
H6A—C6—H6C	109.5	C15—C16—H16A	106.9
H6B—C6—H6C	109.5	C17—C16—H16B	106.9
O2—C7—C8	117.2 (9)	C15—C16—H16B	106.9
O2—C7—H7A	108.0	H16A—C16—H16B	106.7
C8—C7—H7A	108.0	C18—C17—C16	122.2 (14)
O2—C7—H7B	108.0	C18—C17—H17A	106.8
C8—C7—H7B	108.0	C16—C17—H17A	106.8
H7A—C7—H7B	107.3	C18—C17—H17B	106.8
C7—C8—C9	121.1 (11)	C16—C17—H17B	106.8
C7—C8—H8A	107.1	H17A—C17—H17B	106.6
C9—C8—H8A	107.0	C17—C18—H18A	109.5
C7—C8—H8B	107.1	C17—C18—H18B	109.5
C9—C8—H8B	107.1	H18A—C18—H18B	109.5
H8A—C8—H8B	106.8	C17—C18—H18C	109.5
C10—C9—C8	115.4 (13)	H18A—C18—H18C	109.5
C10—C9—H9A	108.4	H18B—C18—H18C	109.5
C6—N1—C1—C2	−59.5 (13)	C7—C8—C9—C10	161.0 (19)
C4—N1—C1—C2	70.9 (17)	C8—C9—C10—C11	−179.9 (18)
C5—N1—C1—C2	−175.0 (11)	C9—C10—C11—C12	−172 (2)
N1—C1—C2—O1	−68.1 (13)	C10—C11—C12—C13	−168 (2)
N1—C1—C2—C3	175.6 (10)	C11—C12—C13—C14	172 (3)
C7—O2—C3—C2	−160.1 (15)	C12—C13—C14—C15	172 (2)
O1—C2—C3—O2	165.6 (11)	C13—C14—C15—C16	179 (2)
C1—C2—C3—O2	−75.0 (16)	C14—C15—C16—C17	−174 (2)
C3—O2—C7—C8	−171.2 (18)	C15—C16—C17—C18	−174 (3)
O2—C7—C8—C9	162.0 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6C···O1i	0.96	2.27	3.229 (13)	174
O1—H1···Br1ii	0.82	2.46	3.272 (6)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6C⋯O1i	0.96	2.27	3.229 (13)	174
O1—H1⋯Br1ii	0.82	2.46	3.272 (6)	170

Symmetry codes: (i) ; (ii) .