2-Hy­droxy-N,N,N-trimethyl-3-tetra­decyl­oxypropan-1-aminium bromide

Wang, X.; Wei, X.; Du, P.

doi:10.1107/S1600536811054651

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o246

doi:10.1107/S1600536811054651

Open

access

2-Hydroxy-N,N,N-trimethyl-3-tetradecyloxypropan-1-aminium bromide

Xiuhong Wang,^a Xilian Wei ^a ^* and Panpan Du ^a

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: weixilian@126.com

(Received 9 November 2011; accepted 19 December 2011; online 23 December 2011)

In the crystal structure of the title compound, C₂₀H₄₄NO₂⁺·Br⁻, the cation and anion are connected via an O—H⋯Br hydrogen bond, forming an ionic pair. The cation is disordered over two conformations related by a mirror plane, and the anion is situated on a mirror plane so that the asymmetric unit contains half of the ionic pair. The long alkyl chain in the cation adopts an all-trans conformation. The crystal packing exhibits weak intermolecular C—H⋯O interactions.

Related literature

For related structures, see: Koh et al. (1993 ); Fu et al. (2009 ); Liu et al. (2010 ). For details of the synthesis, see: Yin et al. (1998 ).

Experimental

Crystal data

C₂₀H₄₄NO₂⁺·Br⁻
M_r = 410.47
Monoclinic, P 2₁ /m
a = 5.9470 (4) Å
b = 7.4331 (5) Å
c = 26.720 (2) Å
β = 92.185 (1)°
V = 1180.30 (15) Å³
Z = 2
Mo Kα radiation
μ = 1.75 mm⁻¹
T = 293 K
0.39 × 0.32 × 0.30 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.548, T_max = 0.621
5657 measured reflections
2251 independent reflections
1430 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.154
S = 0.99
2251 reflections
171 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1D⋯Br1	0.85	2.41	3.207 (6)	157
C19—H19B⋯O1ⁱ	0.96	2.23	3.190 (6)	176
Symmetry code: (i) x+1, y, z.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811054651/cv5198sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811054651/cv5198Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811054651/cv5198Isup3.cml

checkCIF report

Comment top

Cationic surfactants have various applications serving as fabric softeners, disinfectants, demulsifiers, emulsifiers, wetting agents and processing aids. Quaternary ammonium based surfactants are molecules with at least one hydrophobic long alkyl chain attached to a positively charged nitrogen atom. Synthesis of 3-alkoxy-2-hydroxypropyl-N,N,N-trimethylpropan- 1-aminium bromides (RTABs) was described by Yin et al. (1998). As a part of the studies on the chemistry of surfactants, we report here the crystal structure of the title compound (I).

In (I) (Fig. 1), all bond lengths and angles are normal and correspond to those observed in the related compounds (Koh et al., 1993; Fu et al., 2009; Liu et al., 2010). The C3—O2 and C4—O2 bond lengths are 1.411 (10) and 1.373 (7) Å, respectively. The cation and anion are connected by O—H···Br hydrogen bond (Table 1) forming an ionic pair. The cation is disordered over two conformations related by the mirror plane, and anion is situated on a mirror plane so asymmetric unit contains a half of the ionic pair.

The crystal packing exhibits weak intermolecular C—H···O interactions (Table 1).

Related literature top

For related structures, see: Koh et al. (1993); Fu et al. (2009); Liu et al. (2010). For details of the synthesis, see: Yin et al. (1998).

Experimental top

The reaction was carried out under nitrogen atmosphere. Trimethylammonium bromide (0.12 mol) and tetradecyl glcidyl ether (0.1 mol) were added to a stirred solution of ethanol (100 ml) and stirred at 320 K for 24 h. The resulting clear solution was evaporated under vacuum. Colorless crystals suitable for X-ray analysis were obtained by slow evaporation of a ethyl acetate solution over a period of two weeks. (yield 78%,m.p. 342 K) Anal. Calcd(%) for C₂₀H₄₄NO₂⁺Br^- (410.47): C, 57.87; H, 10.72; N, 3.41. Found (%): C, 58.48, H, 10.82 N, 3.48.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, with atom labeling scheme and 50% probability displacement ellipsoids [symmetry code: (A) x, 1/2-y, z]. Only one conformation of the cation is shown. Dashed line denotes hydrogen bond. C-bound H-atoms omitted for clarity.

2-Hydroxy-N,N,N-trimethyl-3-tetradecyloxypropan-1-aminium bromide top

Crystal data top

C₂₀H₄₄NO₂⁺·Br⁻	F(000) = 444
M_r = 410.47	D_x = 1.155 Mg m⁻³
Monoclinic, P2₁/m	Mo Kα radiation, λ = 0.71073 Å
a = 5.9470 (4) Å	Cell parameters from 1899 reflections
b = 7.4331 (5) Å	θ = 2.7–20.7°
c = 26.720 (2) Å	µ = 1.75 mm⁻¹
β = 92.185 (1)°	T = 293 K
V = 1180.30 (15) Å³	Block, colourless
Z = 2	0.39 × 0.32 × 0.30 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2251 independent reflections
Radiation source: fine-focus sealed tube	1430 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
phi and ω scans	θ_max = 25.0°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→6
T_min = 0.548, T_max = 0.621	k = −6→8
5657 measured reflections	l = −30→31

Refinement top

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.154	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0907P)²] where P = (F_o² + 2F_c²)/3
2251 reflections	(Δ/σ)_max = 0.001
171 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₂₀H₄₄NO₂⁺·Br⁻	V = 1180.30 (15) Å³
M_r = 410.47	Z = 2
Monoclinic, P2₁/m	Mo Kα radiation
a = 5.9470 (4) Å	µ = 1.75 mm⁻¹
b = 7.4331 (5) Å	T = 293 K
c = 26.720 (2) Å	0.39 × 0.32 × 0.30 mm
β = 92.185 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2251 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1430 reflections with I > 2σ(I)
T_min = 0.548, T_max = 0.621	R_int = 0.048
5657 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.154	H-atom parameters constrained
S = 0.99	Δρ_max = 0.36 e Å⁻³
2251 reflections	Δρ_min = −0.42 e Å⁻³
171 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Br1	−0.29860 (11)	0.7500	0.07517 (2)	0.0781 (3)
O1	−0.3202 (8)	0.3776 (8)	0.13541 (18)	0.0719 (15)	0.50
H1D	−0.2738	0.4655	0.1183	0.086*	0.50
O2	0.0819 (8)	0.2500	0.23481 (14)	0.1043 (17)
N1	0.0902 (7)	0.2500	0.07672 (15)	0.0570 (11)
C1	0.0206 (14)	0.1957 (11)	0.1295 (3)	0.070 (3)	0.50
H1A	−0.0773	0.0914	0.1269	0.084*	0.50
H1B	0.1538	0.1618	0.1494	0.084*	0.50
C2	−0.1016 (13)	0.3479 (12)	0.1561 (3)	0.064 (2)	0.50
H2	−0.0133	0.4590	0.1549	0.077*	0.50
C3	−0.1261 (14)	0.290 (4)	0.2101 (2)	0.087 (8)	0.50
H3A	−0.1997	0.3853	0.2282	0.104*	0.50
H3B	−0.2218	0.1843	0.2108	0.104*	0.50
C4	0.0878 (14)	0.2500	0.2862 (2)	0.113 (3)
H4A	0.0049	0.1452	0.2968	0.135*	0.50
H4B	0.0049	0.3548	0.2968	0.135*	0.50
C5	0.2932 (11)	0.2500	0.3127 (2)	0.091 (2)
H5A	0.3553	0.3698	0.3092	0.109*	0.50
H5B	0.3907	0.1694	0.2950	0.109*	0.50
C6	0.3204 (15)	0.203 (3)	0.3659 (3)	0.096 (8)	0.50
H6A	0.1945	0.2500	0.3826	0.116*
H6B	0.3032	0.0739	0.3683	0.116*	0.50
C7	0.5191 (12)	0.2500	0.3947 (2)	0.090 (2)
H7A	0.5322	0.3800	0.3935	0.108*	0.50
H7B	0.6454	0.2018	0.3771	0.108*	0.50
C8	0.5521 (14)	0.1965 (14)	0.4480 (3)	0.086 (4)	0.50
H8A	0.4234	0.2500	0.4655	0.103*
H8B	0.5452	0.0662	0.4492	0.103*	0.50
C9	0.7504 (12)	0.2500	0.4770 (2)	0.087 (2)
H9A	0.7576	0.3803	0.4760	0.104*	0.50
H9B	0.8796	0.2057	0.4596	0.104*	0.50
C10	0.7807 (16)	0.1948 (14)	0.5305 (3)	0.089 (4)	0.50
H10A	0.6513	0.2500	0.5479	0.107*
H10B	0.7751	0.0645	0.5315	0.107*	0.50
C11	0.9785 (12)	0.2500	0.5590 (2)	0.090 (2)
H11A	0.9839	0.3803	0.5577	0.108*	0.50
H11B	1.1074	0.2063	0.5414	0.108*	0.50
C12	1.0140 (15)	0.1975 (15)	0.6127 (3)	0.089 (5)	0.50
H12A	0.8865	0.2500	0.6304	0.107*
H12B	1.0059	0.0672	0.6141	0.107*	0.50
C13	1.2124 (13)	0.2500	0.6409 (2)	0.096 (2)
H13A	1.2690	0.3530	0.6229	0.116*	0.50
H13B	1.3187	0.1536	0.6355	0.116*	0.50
C14	1.2474 (15)	0.297 (2)	0.6938 (3)	0.098 (7)	0.50
H14A	1.2309	0.4267	0.6963	0.118*	0.50
H14B	1.1238	0.2500	0.7115	0.118*
C15	1.4523 (14)	0.2500	0.7218 (2)	0.112 (3)
H15A	1.4903	0.1295	0.7110	0.135*	0.50
H15B	1.5678	0.3286	0.7094	0.135*	0.50
C16	1.4849 (15)	0.2500	0.7756 (3)	0.130 (3)
H16A	1.4050	0.3544	0.7875	0.155*	0.50
H16B	1.4050	0.1456	0.7875	0.155*	0.50
C17	1.6923 (17)	0.2500	0.8012 (3)	0.157 (4)
H17A	1.6703	0.2500	0.8366	0.235*
H17B	1.7751	0.3555	0.7923	0.235*	0.50
H17C	1.7751	0.1445	0.7923	0.235*	0.50
C18	−0.1067 (9)	0.2500	0.04103 (18)	0.0646 (15)
H18A	−0.1988	0.3532	0.0471	0.097*	0.50
H18B	−0.1930	0.1424	0.0455	0.097*	0.50
H18C	−0.0558	0.2544	0.0074	0.097*	0.50
C19	0.2289 (7)	0.4126 (7)	0.06755 (16)	0.0844 (13)
H19A	0.2678	0.4158	0.0330	0.127*
H19B	0.3638	0.4084	0.0885	0.127*
H19C	0.1447	0.5186	0.0753	0.127*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0846 (5)	0.0628 (4)	0.0888 (5)	0.000	0.0271 (3)	0.000
O1	0.060 (3)	0.087 (4)	0.069 (3)	0.000 (3)	0.000 (3)	−0.004 (3)
O2	0.089 (3)	0.183 (5)	0.041 (2)	0.000	0.005 (2)	0.000
N1	0.047 (2)	0.074 (3)	0.050 (3)	0.000	0.0014 (19)	0.000
C1	0.071 (5)	0.088 (10)	0.052 (4)	0.015 (4)	−0.003 (4)	0.002 (4)
C2	0.059 (5)	0.087 (5)	0.045 (5)	0.008 (4)	0.003 (4)	−0.002 (4)
C3	0.082 (5)	0.13 (3)	0.052 (4)	−0.001 (6)	0.008 (4)	0.006 (6)
C4	0.108 (6)	0.173 (9)	0.058 (5)	0.000	0.007 (4)	0.000
C5	0.095 (5)	0.139 (6)	0.039 (3)	0.000	0.003 (3)	0.000
C6	0.103 (6)	0.14 (2)	0.047 (4)	0.009 (7)	0.000 (4)	0.000 (5)
C7	0.104 (5)	0.125 (6)	0.042 (4)	0.000	0.009 (3)	0.000
C8	0.100 (6)	0.109 (13)	0.047 (4)	0.000 (5)	0.001 (4)	0.000 (4)
C9	0.105 (5)	0.112 (6)	0.044 (3)	0.000	0.008 (3)	0.000
C10	0.107 (6)	0.114 (13)	0.047 (4)	0.005 (5)	−0.001 (4)	−0.002 (4)
C11	0.103 (5)	0.122 (6)	0.046 (4)	0.000	0.007 (3)	0.000
C12	0.110 (6)	0.110 (14)	0.047 (4)	−0.003 (6)	−0.003 (4)	−0.005 (4)
C13	0.115 (6)	0.127 (6)	0.048 (4)	0.000	0.007 (4)	0.000
C14	0.117 (7)	0.13 (2)	0.043 (4)	0.025 (8)	−0.002 (4)	0.000 (5)
C15	0.113 (6)	0.169 (9)	0.055 (4)	0.000	0.010 (4)	0.000
C16	0.137 (8)	0.197 (10)	0.053 (5)	0.000	−0.017 (5)	0.000
C17	0.132 (8)	0.273 (15)	0.065 (5)	0.000	0.000 (5)	0.000
C18	0.064 (3)	0.087 (4)	0.042 (3)	0.000	0.000 (3)	0.000
C19	0.079 (3)	0.081 (3)	0.094 (3)	−0.015 (2)	0.004 (2)	−0.007 (2)

Geometric parameters (Å, º) top

O1—C2	1.411 (8)	C9—C8ⁱ	1.441 (9)
O1—H1D	0.8500	C9—C10	1.493 (9)
O2—C4	1.373 (7)	C9—C10ⁱ	1.493 (9)
O2—C3ⁱ	1.411 (10)	C9—H9A	0.9700
O2—C3	1.411 (10)	C9—H9B	0.9700
N1—C18	1.482 (6)	C10—C10ⁱ	0.82 (2)
N1—C19	1.489 (5)	C10—C11	1.437 (10)
N1—C19ⁱ	1.489 (5)	C10—H10A	1.0021
N1—C1	1.538 (8)	C10—H10B	0.9700
N1—C1ⁱ	1.538 (8)	C11—C10ⁱ	1.437 (10)
C1—C1ⁱ	0.808 (16)	C11—C12	1.493 (9)
C1—C2ⁱ	1.087 (9)	C11—C12ⁱ	1.493 (9)
C1—C2	1.535 (10)	C11—H11A	0.9700
C1—H1A	0.9700	C11—H11B	0.9701
C1—H1B	0.9699	C12—C12ⁱ	0.78 (2)
C2—C1ⁱ	1.087 (9)	C12—C13	1.430 (10)
C2—C2ⁱ	1.455 (17)	C12—H12A	0.9892
C2—C3	1.518 (12)	C12—H12B	0.9700
C2—C3ⁱ	1.780 (19)	C13—C12ⁱ	1.430 (10)
C2—H2	0.9800	C13—C14	1.465 (10)
C3—C3ⁱ	0.59 (6)	C13—C14ⁱ	1.465 (10)
C3—C2ⁱ	1.780 (19)	C13—H13A	0.9700
C3—H3A	0.9700	C13—H13B	0.9700
C3—H3B	0.9700	C14—C14ⁱ	0.70 (4)
C4—C5	1.389 (9)	C14—C15	1.448 (11)
C4—H4A	0.9700	C14—H14A	0.9701
C4—H4B	0.9700	C14—H14B	0.9543
C5—C6	1.465 (10)	C15—C16	1.443 (9)
C5—C6ⁱ	1.465 (10)	C15—C14ⁱ	1.448 (11)
C5—H5A	0.9700	C15—H15A	0.9701
C5—H5B	0.9700	C15—H15B	0.9701
C6—C6ⁱ	0.69 (4)	C16—C17	1.387 (11)
C6—C7	1.428 (10)	C16—H16A	0.9700
C6—H6A	0.9514	C16—H16B	0.9700
C6—H6B	0.9699	C17—H17A	0.9600
C7—C6ⁱ	1.428 (10)	C17—H17B	0.9600
C7—C8	1.486 (8)	C17—H17C	0.9600
C7—C8ⁱ	1.486 (8)	C18—H18A	0.9600
C7—H7A	0.9700	C18—H18B	0.9600
C7—H7B	0.9698	C18—H18C	0.9600
C8—C8ⁱ	0.80 (2)	C19—H19A	0.9600
C8—C9	1.441 (9)	C19—H19B	0.9600
C8—H8A	0.9952	C19—H19C	0.9600
C8—H8B	0.9700

C2—O1—H1D	91.1	C9—C8—H8A	105.5
C4—O2—C3ⁱ	117.1 (6)	C7—C8—H8A	105.5
C4—O2—C3	117.1 (6)	C8ⁱ—C8—H8B	176.9
C3ⁱ—O2—C3	24 (2)	C9—C8—H8B	107.1
C18—N1—C19	108.9 (3)	C7—C8—H8B	107.1
C18—N1—C19ⁱ	108.9 (3)	H8A—C8—H8B	110.4
C19—N1—C19ⁱ	108.5 (5)	C8ⁱ—C9—C8	32.0 (8)
C18—N1—C1	110.9 (4)	C8ⁱ—C9—C10	131.0 (7)
C19—N1—C1	122.3 (4)	C8—C9—C10	120.3 (6)
C19ⁱ—N1—C1	96.2 (4)	C8ⁱ—C9—C10ⁱ	120.3 (6)
C18—N1—C1ⁱ	110.9 (4)	C8—C9—C10ⁱ	131.0 (7)
C19—N1—C1ⁱ	96.2 (4)	C10—C9—C10ⁱ	31.9 (8)
C19ⁱ—N1—C1ⁱ	122.3 (4)	C8ⁱ—C9—H9A	75.3
C1—N1—C1ⁱ	30.5 (6)	C8—C9—H9A	107.3
C18—N1—Br1	65.78 (10)	C10—C9—H9A	107.2
C19—N1—Br1	66.7 (2)	C10ⁱ—C9—H9A	75.4
C19ⁱ—N1—Br1	169.6 (3)	C8ⁱ—C9—H9B	119.0
C1—N1—Br1	94.1 (3)	C8—C9—H9B	107.3
C1ⁱ—N1—Br1	68.0 (3)	C10—C9—H9B	107.2
C1ⁱ—C1—C2ⁱ	107.3 (6)	C10ⁱ—C9—H9B	118.9
C1ⁱ—C1—C2	42.5 (4)	H9A—C9—H9B	106.9
C2ⁱ—C1—C2	64.8 (8)	C10ⁱ—C10—C11	73.4 (4)
C1ⁱ—C1—N1	74.8 (3)	C10ⁱ—C10—C9	74.0 (4)
C2ⁱ—C1—N1	152.8 (8)	C11—C10—C9	119.8 (7)
C2—C1—N1	112.4 (6)	C10ⁱ—C10—H10A	65.8
C1ⁱ—C1—H1A	143.0	C11—C10—H10A	105.3
C2ⁱ—C1—H1A	52.6	C9—C10—H10A	105.4
C2—C1—H1A	109.1	C10ⁱ—C10—H10B	177.4
N1—C1—H1A	109.1	C11—C10—H10B	107.4
C1ⁱ—C1—H1B	105.0	C9—C10—H10B	107.4
C2ⁱ—C1—H1B	96.7	H10A—C10—H10B	111.6
C2—C1—H1B	109.1	C10ⁱ—C11—C10	33.2 (9)
N1—C1—H1B	109.1	C10ⁱ—C11—C12	131.8 (7)
H1A—C1—H1B	107.9	C10—C11—C12	121.2 (6)
C1ⁱ—C2—O1	114.8 (7)	C10ⁱ—C11—C12ⁱ	121.2 (6)
C1ⁱ—C2—C2ⁱ	72.7 (6)	C10—C11—C12ⁱ	131.8 (7)
O1—C2—C2ⁱ	99.0 (4)	C12—C11—C12ⁱ	30.3 (8)
C1ⁱ—C2—C3	129.0 (11)	C10ⁱ—C11—H11A	73.9
O1—C2—C3	107.3 (6)	C10—C11—H11A	107.0
C2ⁱ—C2—C3	73.5 (11)	C12—C11—H11A	107.0
C1ⁱ—C2—C1	30.2 (7)	C12ⁱ—C11—H11A	76.7
O1—C2—C1	112.3 (6)	C10ⁱ—C11—H11B	118.9
C2ⁱ—C2—C1	42.5 (4)	C10—C11—H11B	107.0
C3—C2—C1	107.3 (11)	C12—C11—H11B	107.0
C1ⁱ—C2—C3ⁱ	116.0 (9)	C12ⁱ—C11—H11B	117.9
O1—C2—C3ⁱ	107.8 (6)	H11A—C11—H11B	106.8
C2ⁱ—C2—C3ⁱ	54.9 (8)	C12ⁱ—C12—C13	74.1 (4)
C3—C2—C3ⁱ	18.7 (18)	C12ⁱ—C12—C11	74.8 (4)
C1—C2—C3ⁱ	90.4 (8)	C13—C12—C11	121.2 (7)
C1ⁱ—C2—H2	81.7	C12ⁱ—C12—H12A	66.7
O1—C2—H2	110.0	C13—C12—H12A	105.8
C2ⁱ—C2—H2	147.4	C11—C12—H12A	105.8
C3—C2—H2	110.0	C12ⁱ—C12—H12B	176.3
C1—C2—H2	110.0	C13—C12—H12B	107.1
C3ⁱ—C2—H2	124.9	C11—C12—H12B	107.0
C3ⁱ—C3—O2	77.9 (11)	H12A—C12—H12B	109.6
C3ⁱ—C3—C2	106.5 (11)	C12ⁱ—C13—C12	31.7 (9)
O2—C3—C2	112.9 (6)	C12ⁱ—C13—C14	121.8 (7)
C3ⁱ—C3—C2ⁱ	54.9 (8)	C12—C13—C14	131.1 (7)
O2—C3—C2ⁱ	99.2 (11)	C12ⁱ—C13—C14ⁱ	131.1 (7)
C2—C3—C2ⁱ	51.6 (7)	C12—C13—C14ⁱ	121.8 (7)
C3ⁱ—C3—H3A	136.9	C14—C13—C14ⁱ	27.7 (14)
O2—C3—H3A	109.0	C12ⁱ—C13—H13A	79.6
C2—C3—H3A	109.0	C12—C13—H13A	104.5
C2ⁱ—C3—H3A	151.0	C14—C13—H13A	104.4
C3ⁱ—C3—H3B	36.0	C14ⁱ—C13—H13A	128.8
O2—C3—H3B	109.0	C12ⁱ—C13—H13B	130.8
C2—C3—H3B	109.0	C12—C13—H13B	104.5
C2ⁱ—C3—H3B	67.4	C14—C13—H13B	104.5
H3A—C3—H3B	107.8	C14ⁱ—C13—H13B	84.1
O2—C4—C5	119.9 (6)	H13A—C13—H13B	105.6
O2—C4—H4A	107.3	C14ⁱ—C14—C15	76.0 (7)
C5—C4—H4A	107.3	C14ⁱ—C14—C13	76.2 (7)
O2—C4—H4B	107.3	C15—C14—C13	121.8 (9)
C5—C4—H4B	107.3	C14ⁱ—C14—H14A	172.9
H4A—C4—H4B	106.9	C15—C14—H14A	106.9
C4—C5—C6	123.9 (7)	C13—C14—H14A	106.9
C4—C5—C6ⁱ	123.9 (6)	C14ⁱ—C14—H14B	68.5
C6—C5—C6ⁱ	27.4 (16)	C15—C14—H14B	107.8
C4—C5—H5A	106.4	C13—C14—H14B	107.8
C6—C5—H5A	106.4	H14A—C14—H14B	104.4
C6ⁱ—C5—H5A	81.3	C16—C15—C14ⁱ	126.3 (7)
C4—C5—H5B	106.3	C16—C15—C14	126.3 (7)
C6—C5—H5B	106.3	C14ⁱ—C15—C14	28.0 (14)
C6ⁱ—C5—H5B	125.0	C16—C15—H15A	105.7
H5A—C5—H5B	106.4	C14ⁱ—C15—H15A	79.9
C6ⁱ—C6—C7	75.9 (8)	C14—C15—H15A	105.8
C6ⁱ—C6—C5	76.3 (8)	C16—C15—H15B	105.7
C7—C6—C5	121.6 (9)	C14ⁱ—C15—H15B	124.2
C6ⁱ—C6—H6A	68.6	C14—C15—H15B	105.7
C7—C6—H6A	108.0	H15A—C15—H15B	106.2
C5—C6—H6A	108.0	C17—C16—C15	125.0 (8)
C6ⁱ—C6—H6B	172.7	C17—C16—H16A	106.1
C7—C6—H6B	107.0	C15—C16—H16A	106.1
C5—C6—H6B	107.0	C17—C16—H16B	106.1
H6A—C6—H6B	104.1	C15—C16—H16B	106.1
C6ⁱ—C7—C6	28.1 (16)	H16A—C16—H16B	106.3
C6ⁱ—C7—C8	131.2 (7)	C16—C17—H17A	109.5
C6—C7—C8	121.9 (7)	C16—C17—H17B	109.5
C6ⁱ—C7—C8ⁱ	121.9 (7)	H17A—C17—H17B	109.5
C6—C7—C8ⁱ	131.2 (7)	C16—C17—H17C	109.5
C8—C7—C8ⁱ	31.0 (8)	H17A—C17—H17C	109.5
C6ⁱ—C7—H7A	78.9	H17B—C17—H17C	109.5
C6—C7—H7A	106.9	N1—C18—H18A	109.5
C8—C7—H7A	106.8	N1—C18—H18B	109.5
C8ⁱ—C7—H7A	75.9	H18A—C18—H18B	109.5
C6ⁱ—C7—H7B	118.0	N1—C18—H18C	109.5
C6—C7—H7B	106.8	H18A—C18—H18C	109.5
C8—C7—H7B	106.8	H18B—C18—H18C	109.5
C8ⁱ—C7—H7B	119.2	N1—C19—H19A	109.5
H7A—C7—H7B	106.7	N1—C19—H19B	109.5
C8ⁱ—C8—C9	74.0 (4)	H19A—C19—H19B	109.5
C8ⁱ—C8—C7	74.5 (4)	N1—C19—H19C	109.5
C9—C8—C7	121.1 (7)	H19A—C19—H19C	109.5
C8ⁱ—C8—H8A	66.5	H19B—C19—H19C	109.5

C18—N1—C1—C1ⁱ	−95.96 (18)	C4—C5—C6—C6ⁱ	−99.4 (6)
C19—N1—C1—C1ⁱ	34.6 (3)	C4—C5—C6—C7	−163.1 (8)
C19ⁱ—N1—C1—C1ⁱ	151.1 (3)	C6ⁱ—C5—C6—C7	−63.7 (13)
Br1—N1—C1—C1ⁱ	−30.35 (7)	C5—C6—C7—C6ⁱ	63.9 (13)
C18—N1—C1—C2ⁱ	2.4 (19)	C6ⁱ—C6—C7—C8	118.7 (7)
C19—N1—C1—C2ⁱ	132.9 (17)	C5—C6—C7—C8	−177.4 (10)
C19ⁱ—N1—C1—C2ⁱ	−110.5 (18)	C6ⁱ—C6—C7—C8ⁱ	81.5 (9)
C1ⁱ—N1—C1—C2ⁱ	98.3 (18)	C5—C6—C7—C8ⁱ	145.4 (9)
Br1—N1—C1—C2ⁱ	68.0 (18)	C6ⁱ—C7—C8—C8ⁱ	−84.7 (11)
C18—N1—C1—C2	−75.7 (6)	C6—C7—C8—C8ⁱ	−118.0 (10)
C19—N1—C1—C2	54.9 (8)	C6ⁱ—C7—C8—C9	−144.6 (12)
C19ⁱ—N1—C1—C2	171.4 (6)	C6—C7—C8—C9	−177.9 (10)
C1ⁱ—N1—C1—C2	20.3 (6)	C8ⁱ—C7—C8—C9	−59.9 (8)
Br1—N1—C1—C2	−10.1 (6)	C7—C8—C9—C8ⁱ	60.1 (8)
C2ⁱ—C1—C2—C1ⁱ	180.000 (4)	C8ⁱ—C8—C9—C10	119.9 (6)
N1—C1—C2—C1ⁱ	−29.6 (9)	C7—C8—C9—C10	−179.9 (7)
C1ⁱ—C1—C2—O1	101.3 (7)	C8ⁱ—C8—C9—C10ⁱ	82.6 (6)
C2ⁱ—C1—C2—O1	−78.7 (7)	C7—C8—C9—C10ⁱ	142.7 (7)
N1—C1—C2—O1	71.7 (8)	C8ⁱ—C9—C10—C10ⁱ	−82.4 (6)
C1ⁱ—C1—C2—C2ⁱ	180.000 (3)	C8—C9—C10—C10ⁱ	−120.0 (7)
N1—C1—C2—C2ⁱ	150.4 (9)	C8ⁱ—C9—C10—C11	−142.0 (8)
C1ⁱ—C1—C2—C3	−141.1 (10)	C8—C9—C10—C11	−179.6 (7)
C2ⁱ—C1—C2—C3	38.9 (10)	C10ⁱ—C9—C10—C11	−59.6 (8)
N1—C1—C2—C3	−170.7 (7)	C9—C10—C11—C10ⁱ	59.9 (8)
C1ⁱ—C1—C2—C3ⁱ	−149.2 (8)	C10ⁱ—C10—C11—C12	120.0 (7)
C2ⁱ—C1—C2—C3ⁱ	30.8 (8)	C9—C10—C11—C12	179.9 (7)
N1—C1—C2—C3ⁱ	−178.9 (6)	C10ⁱ—C10—C11—C12ⁱ	84.3 (7)
C4—O2—C3—C3ⁱ	−96.3 (6)	C9—C10—C11—C12ⁱ	144.2 (7)
C4—O2—C3—C2	160.7 (11)	C10ⁱ—C11—C12—C12ⁱ	−81.1 (7)
C3ⁱ—O2—C3—C2	−102.9 (16)	C10—C11—C12—C12ⁱ	−120.6 (7)
C4—O2—C3—C2ⁱ	−147.2 (4)	C10ⁱ—C11—C12—C13	−141.5 (8)
C3ⁱ—O2—C3—C2ⁱ	−50.9 (9)	C10—C11—C12—C13	179.0 (7)
C1ⁱ—C2—C3—C3ⁱ	−50.3 (13)	C12ⁱ—C11—C12—C13	−60.4 (8)
O1—C2—C3—C3ⁱ	94.5 (6)	C11—C12—C13—C12ⁱ	60.7 (8)
C2ⁱ—C2—C3—C3ⁱ	0.000 (9)	C12ⁱ—C12—C13—C14	85.3 (10)
C1—C2—C3—C3ⁱ	−26.3 (6)	C11—C12—C13—C14	146.0 (10)
C1ⁱ—C2—C3—O2	33 (3)	C12ⁱ—C12—C13—C14ⁱ	118.0 (9)
O1—C2—C3—O2	178.0 (14)	C11—C12—C13—C14ⁱ	178.6 (9)
C2ⁱ—C2—C3—O2	83.5 (17)	C12ⁱ—C13—C14—C14ⁱ	118.9 (7)
C1—C2—C3—O2	57.2 (19)	C12—C13—C14—C14ⁱ	80.9 (8)
C3ⁱ—C2—C3—O2	83.5 (17)	C12ⁱ—C13—C14—C15	−177.5 (9)
C1ⁱ—C2—C3—C2ⁱ	−50.3 (13)	C12—C13—C14—C15	144.4 (9)
O1—C2—C3—C2ⁱ	94.5 (6)	C14ⁱ—C13—C14—C15	63.5 (12)
C1—C2—C3—C2ⁱ	−26.3 (6)	C14ⁱ—C14—C15—C16	−100.6 (6)
C3ⁱ—C2—C3—C2ⁱ	0.000 (15)	C13—C14—C15—C16	−164.2 (7)
C3ⁱ—O2—C4—C5	166.3 (13)	C13—C14—C15—C14ⁱ	−63.6 (12)
C3—O2—C4—C5	−166.3 (13)	C14ⁱ—C15—C16—C17	162.5 (9)
O2—C4—C5—C6	−163.4 (9)	C14—C15—C16—C17	−162.5 (9)
O2—C4—C5—C6ⁱ	163.4 (9)

Symmetry code: (i) x, −y+1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1D···Br1	0.85	2.41	3.207 (6)	157
C19—H19B···O1ⁱⁱ	0.96	2.23	3.190 (6)	176

Symmetry code: (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₀H₄₄NO₂⁺·Br⁻
M_r	410.47
Crystal system, space group	Monoclinic, P2₁/m
Temperature (K)	293
a, b, c (Å)	5.9470 (4), 7.4331 (5), 26.720 (2)
β (°)	92.185 (1)
V (Å³)	1180.30 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.75
Crystal size (mm)	0.39 × 0.32 × 0.30

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.548, 0.621
No. of measured, independent and observed [I > 2σ(I)] reflections	5657, 2251, 1430
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.154, 0.99
No. of reflections	2251
No. of parameters	171
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.42

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1D···Br1	0.85	2.41	3.207 (6)	156.5
C19—H19B···O1ⁱ	0.96	2.23	3.190 (6)	175.8

Symmetry code: (i) x+1, y, z.

Acknowledgements

We acknowledge the National Natural Science Foundation of China (grant No. 21073081) for financial support.

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fu, S., Wei, Z., Wei, X. & Wu, T. (2009). Acta Cryst. E65, o1836. Web of Science CSD CrossRef IUCr Journals Google Scholar
Koh, L. L., Xu, Y., Gan, L. M., Chew, C. H. & Lee, K. C. (1993). Acta Cryst. C49, 1032–1035. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Liu, J., Wei, Z., Wei, X. & Zhang, C. (2010). Acta Cryst. E66, o2865. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yin, B. L., Zhang, G. Y. & Wei, X. L. (1998). China Surfact. Deterg. Cosmet. 4, 18–22. Google Scholar