2-Hy-droxy-N,N,N-trimethyl-3-tetra-decyl-oxypropan-1-aminium bromide.

In the crystal structure of the title compound, C(20)H(44)NO(2) (+)·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 inter-molecular C-H⋯O inter-actions.

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 +·n class="Chemical">Br−

M = 410.47

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.154

S = 0.99

2251 reflections

171 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.42 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAIn class="Chemical">NT (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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811054651/cv5198sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811054651/cv5198Isup3.cml

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

C20H44NO2+·Br−	F(000) = 444
Mr = 410.47	Dx = 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

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

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(Fo2) + (0.0907P)2] where P = (Fo2 + 2Fc2)/3
2251 reflections	(Δ/σ)max = 0.001
171 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.42 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	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*

	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)

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)

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.

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) .