(2S,NS)-N-Allyl-N-benzyl-1-hydr­oxy-3-(4-hydroxy­phen­yl)-N-methyl­propan-2-aminium bromide

Wu, H.-F.; Luo, Y.-G.; Yu, K.-B.; Zhang, G.-L.; Pan, X.-F.

doi:10.1107/S1600536808023210

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1621

doi:10.1107/S1600536808023210

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(2S,NS)-N-Allyl-N-benzyl-1-hydroxy-3-(4-hydroxyphenyl)-N-methylpropan-2-aminium bromide

Hua-Fang Wu,^a Ying-Gang Luo,^b Kai-Bei Yu,^c Guo-Lin Zhang ^b ^* and Xin-Fu Pan ^a ^*

^aDepartment of Chemistry, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, People's Republic of China, ^bChengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, People's Republic of China, and ^cChengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, People's Republic of China
^*Correspondence e-mail: hbwuhf@yahoo.com.cn,

(Received 30 June 2008; accepted 23 July 2008; online 31 July 2008)

The title compound, C₂₀H₂₆NO₂⁺·Br⁻, is an N-chiral quaternary ammonium salt synthesized from (2S*)-N-benzyl-N-methyltyrosine methyl ester. The dihedral angle between the phenyl ring and the benzene ring is 11.61 (19)°. In the crystal structure, the allyl group is disordered over two positions with site occupancy factors of ca 0.8 and 0.2. The bromide anion links to the quaternary ammonium cations via O—H⋯Br hydrogen bonding. An intramolecular O—H⋯Br hydrogen bond is also observed.

Related literature

For general background, see: Maruoka & Ooi (2003 ); Ooi & Maruoka (2007 ). For a related structure, see: Tayama & Tanaka (2007 ). For synthesis, see: White & Konopelski (2005 ).

Experimental

Crystal data

C₂₀H₂₆NO₂⁺·Br⁻
M_r = 392.33
Orthorhombic, P 2₁ 2₁ 2₁
a = 10.3716 (10) Å
b = 12.1566 (10) Å
c = 15.6790 (16) Å
V = 1976.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 2.09 mm⁻¹
T = 293 (2) K
0.45 × 0.43 × 0.40 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.406, T_max = 0.433
18872 measured reflections
4524 independent reflections
2606 reflections with I > 2σ(I)
R_int = 0.057

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.211
S = 1.00
4524 reflections
225 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.89 e Å⁻³
Δρ_min = −0.69 e Å⁻³
Absolute structure: Flack (1983 ), with 1949 Friedel pairs
Flack parameter: 0.009 (19)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯Br1	0.82	2.43	3.231 (4)	167
O2—H2O⋯Br1ⁱ	0.82	2.38	3.192 (5)	171
Symmetry code: (i) x, y+1, z.

Data collection: RAPID-AUTO (Rigaku, 2004 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808023210/xu2435sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808023210/xu2435Isup2.hkl

checkCIF report

Comment top

As an important class of asymmetric catalysts of phase-transfer catalysts, chiral quaternary ammonium salts show great application in asymmetric organic synthesis (Maruoka & Ooi, 2003; Ooi & Maruoka, 2007). The title compound is a N-chiral quaternary ammonium salt (N-CQAS), we present here its structure.

The molecular structure is shown in Fig. 1. The quaternary ammonium cation displays an extended structure, the C14—N1—C8—C7 torsion angle is 179.3 (5)°. The terminal C1-benzene and C15-phenyl rings are nearly parallel to each other [dihedral angle 11.61 (19)°], and approximately perpendicular to the central C7/C6/N1/C14 mean plane with dihedral angles of 85.1 (3) and 88.8 (4)°, respectively. Bond lengths and angles agree with those found in a reported N-chiral quaternary ammonium salt (Tayama & Tanaka, 2007).

In the crystal structure the Br^- anion links with the quaternary ammonium cations via O—H···Br hydrogen bonding (Table 1), to form the one dimensional supra-molecular structure along the b axis (Fig. 2).

Related literature top

For general background, see: Maruoka & Ooi (2003); Ooi & Maruoka (2007). For a related structure, see: Tayama & Tanaka (2007). For synthesis, see: White & Konopelski (2005).

Experimental top

(2S*)-N-Benzyl-N-methyltyrosine methyl ester (White & Konopelski, 2005) (1 mmol) was reduced by lithium aluminium hydride (1 mmol) to afford (2S*)-N-Benzyl-N-methyl-2-amino-3-(4-hydroxyphenyl)propan-1-ol, which was then dissolved in absolute acetonitrile (5 ml), and allyl bromide (2 mmol) was added. The mixture was heated to reflux for 42 h. After being cooled to room temperature, the excess allyl bromide and acetonitrile were removed under reduced pressure. The residue was purified by flash chromatography eluted with ethyl acetate/methanol (8:1) to afford the diastereomeric mixture of the N-CQAS with yields (90%). The mixture was recrystallized from ethanol to afford the single crystals of the title compound. Yield (41%).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO (Rigaku, 2004); data reduction: RAPID-AUTO (Rigaku, 2004); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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, displacement ellipsoids are drawn at the 30% probability level. The minor disordered component has been omitted for clarity.
	Fig. 2. The unit cell packing diagram of the title compound. Dashed lines indicate hydrogen bonding.

(2S*,NS*)-N-Allyl-N-benzyl-1-hydroxy-3- (4-hydroxyphenyl)-N-methylpropan-2-aminium bromide top

Crystal data top

C₂₀H₂₆NO₂⁺·Br⁻	D_x = 1.318 Mg m⁻³
M_r = 392.33	Melting point: 449(5) K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 10762 reflections
a = 10.3716 (10) Å	θ = 3.1–27.4°
b = 12.1566 (10) Å	µ = 2.09 mm⁻¹
c = 15.6790 (16) Å	T = 293 K
V = 1976.9 (3) Å³	Block, colourless
Z = 4	0.45 × 0.43 × 0.40 mm
F(000) = 816

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	4524 independent reflections
Radiation source: Rotating anode	2606 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −13→13
T_min = 0.406, T_max = 0.434	k = −15→15
18872 measured reflections	l = −20→20

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.054	w = 1/[σ²(F_o²) + (0.128P)² + 0.338P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.211	(Δ/σ)_max = 0.001
S = 1.00	Δρ_max = 0.89 e Å⁻³
4524 reflections	Δρ_min = −0.69 e Å⁻³
225 parameters	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
2 restraints	Extinction coefficient: 0.058 (6)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), with 1949 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.009 (19)

Crystal data top

C₂₀H₂₆NO₂⁺·Br⁻	V = 1976.9 (3) Å³
M_r = 392.33	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 10.3716 (10) Å	µ = 2.09 mm⁻¹
b = 12.1566 (10) Å	T = 293 K
c = 15.6790 (16) Å	0.45 × 0.43 × 0.40 mm

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	4524 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2606 reflections with I > 2σ(I)
T_min = 0.406, T_max = 0.434	R_int = 0.057
18872 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	H-atom parameters constrained
wR(F²) = 0.211	Δρ_max = 0.89 e Å⁻³
S = 1.00	Δρ_min = −0.69 e Å⁻³
4524 reflections	Absolute structure: Flack (1983), with 1949 Friedel pairs
225 parameters	Absolute structure parameter: 0.009 (19)
2 restraints

Special details top

Experimental. IR (KBr): 3297, 3034, 1612, 1515, 1464, 1264, 1058, 850 (cm^-1); ¹³CNMR (150 MHz, DMSO-d₆, δ, p.p.m.): 156.8, 133.7, 130.8, 129.4, 128.5, 127.4, 126.9, 126.8, 116.0, 73.9, 63.7, 62.9, 56.6, 47.0, 29.6.

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	0.63828 (7)	0.06624 (5)	0.31732 (5)	0.0766 (3)
O1	0.6728 (4)	0.3120 (4)	0.3923 (3)	0.0748 (12)
H1O	0.6764	0.2479	0.3762	0.090*
O2	0.7918 (4)	0.8588 (4)	0.3897 (4)	0.0863 (14)
H2O	0.7452	0.9091	0.3736	0.104*
N1	0.3651 (4)	0.3213 (4)	0.4017 (3)	0.0552 (10)
C1	0.7120 (6)	0.5784 (6)	0.4504 (5)	0.0739 (17)
H1	0.7557	0.5151	0.4668	0.089*
C2	0.7823 (6)	0.6731 (5)	0.4309 (5)	0.0739 (18)
H2	0.8718	0.6726	0.4334	0.089*
C3	0.7171 (6)	0.7673 (5)	0.4080 (4)	0.0680 (16)
C4	0.5853 (6)	0.7668 (5)	0.4011 (4)	0.0696 (16)
H4	0.5420	0.8296	0.3830	0.083*
C5	0.5173 (6)	0.6733 (5)	0.4210 (5)	0.0667 (16)
H5	0.4278	0.6747	0.4178	0.080*
C6	0.5784 (5)	0.5767 (5)	0.4459 (4)	0.0595 (13)
C7	0.5053 (7)	0.4747 (5)	0.4658 (4)	0.0666 (15)
H7A	0.4282	0.4936	0.4976	0.080*
H7B	0.5578	0.4271	0.5013	0.080*
C8	0.4670 (5)	0.4131 (4)	0.3849 (4)	0.0538 (12)
H8	0.4261	0.4670	0.3471	0.065*
C9	0.5867 (5)	0.3719 (5)	0.3389 (4)	0.0576 (13)
H9A	0.5603	0.3251	0.2919	0.069*
H9B	0.6322	0.4345	0.3149	0.069*
C10	0.4099 (6)	0.2377 (5)	0.4638 (4)	0.0606 (13)
H10A	0.3393	0.1905	0.4790	0.073*
H10B	0.4419	0.2738	0.5140	0.073*
H10C	0.4775	0.1947	0.4386	0.073*
C11	0.2426 (6)	0.3716 (6)	0.4391 (4)	0.0707 (16)
H11A	0.1774	0.3147	0.4435	0.085*
H11B	0.2611	0.3974	0.4964	0.085*
C12	0.1902 (7)	0.4635 (6)	0.3892 (5)	0.092 (2)	0.778 (18)
H12	0.1973	0.4594	0.3302	0.111*	0.778 (18)
C13	0.1339 (16)	0.5511 (10)	0.4216 (8)	0.132 (6)	0.778 (18)
H13A	0.1250	0.5581	0.4804	0.158*	0.778 (18)
H13B	0.1030	0.6060	0.3857	0.158*	0.778 (18)
C12'	0.1902 (7)	0.4635 (6)	0.3892 (5)	0.092 (2)	0.222 (18)
H12'	0.2394	0.5064	0.3525	0.111*	0.222 (18)
C13'	0.0657 (12)	0.479 (5)	0.402 (3)	0.132 (6)	0.222 (18)
H13C	0.0212	0.4331	0.4396	0.158*	0.222 (18)
H13D	0.0225	0.5346	0.3736	0.158*	0.222 (18)
C14	0.3330 (5)	0.2665 (5)	0.3165 (4)	0.0644 (14)
H14A	0.3090	0.3235	0.2762	0.077*
H14B	0.4106	0.2317	0.2950	0.077*
C15	0.2279 (6)	0.1823 (6)	0.3179 (5)	0.0728 (17)
C16	0.2603 (7)	0.0727 (7)	0.3287 (5)	0.086 (2)
H16	0.3459	0.0529	0.3372	0.103*
C17	0.1623 (10)	−0.0099 (9)	0.3266 (6)	0.111 (3)
H17	0.1820	−0.0839	0.3346	0.133*
C18	0.0386 (10)	0.0242 (12)	0.3125 (7)	0.121 (4)
H18	−0.0263	−0.0285	0.3114	0.145*
C19	0.0055 (9)	0.1317 (14)	0.3001 (7)	0.119 (4)
H19	−0.0799	0.1514	0.2902	0.143*
C20	0.1000 (6)	0.2092 (8)	0.3026 (5)	0.093 (2)
H20	0.0781	0.2826	0.2938	0.112*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0760 (4)	0.0657 (4)	0.0881 (5)	0.0026 (3)	−0.0014 (4)	−0.0123 (3)
O1	0.066 (2)	0.060 (2)	0.098 (3)	0.004 (2)	−0.012 (2)	−0.007 (2)
O2	0.069 (3)	0.062 (2)	0.127 (4)	−0.015 (2)	0.000 (3)	0.015 (3)
N1	0.048 (2)	0.066 (3)	0.051 (2)	−0.006 (2)	0.003 (2)	0.0028 (19)
C1	0.068 (4)	0.060 (4)	0.093 (5)	0.006 (3)	−0.008 (3)	0.002 (4)
C2	0.061 (3)	0.055 (3)	0.105 (5)	0.001 (3)	−0.007 (3)	0.008 (3)
C3	0.066 (3)	0.057 (3)	0.081 (4)	−0.014 (3)	0.001 (3)	−0.001 (3)
C4	0.068 (3)	0.057 (3)	0.083 (4)	−0.001 (3)	−0.008 (3)	0.000 (3)
C5	0.061 (3)	0.059 (3)	0.081 (4)	−0.007 (3)	0.002 (3)	−0.004 (3)
C6	0.065 (3)	0.048 (3)	0.065 (3)	−0.005 (3)	0.002 (3)	−0.004 (3)
C7	0.076 (4)	0.059 (3)	0.065 (4)	−0.007 (3)	0.002 (3)	−0.002 (3)
C8	0.055 (3)	0.053 (3)	0.054 (3)	−0.009 (2)	0.001 (2)	0.007 (2)
C9	0.055 (3)	0.054 (3)	0.064 (3)	−0.002 (2)	0.003 (2)	0.001 (2)
C10	0.067 (3)	0.055 (3)	0.060 (3)	−0.012 (3)	−0.001 (3)	0.012 (2)
C11	0.060 (3)	0.087 (4)	0.065 (4)	0.011 (3)	0.009 (3)	−0.003 (3)
C12	0.063 (4)	0.115 (7)	0.099 (5)	0.019 (4)	0.010 (4)	0.011 (5)
C13	0.178 (14)	0.128 (11)	0.089 (7)	0.077 (12)	−0.012 (8)	−0.028 (7)
C12'	0.063 (4)	0.115 (7)	0.099 (5)	0.019 (4)	0.010 (4)	0.011 (5)
C13'	0.178 (14)	0.128 (11)	0.089 (7)	0.077 (12)	−0.012 (8)	−0.028 (7)
C14	0.057 (3)	0.086 (4)	0.050 (3)	−0.013 (3)	0.000 (3)	−0.004 (3)
C15	0.059 (3)	0.097 (5)	0.062 (3)	−0.020 (3)	0.007 (3)	−0.014 (4)
C16	0.071 (4)	0.100 (5)	0.086 (5)	−0.031 (4)	0.010 (3)	−0.024 (5)
C17	0.122 (8)	0.113 (7)	0.097 (6)	−0.055 (6)	0.026 (5)	−0.032 (5)
C18	0.093 (6)	0.193 (12)	0.076 (5)	−0.070 (7)	0.017 (5)	−0.032 (7)
C19	0.066 (5)	0.203 (11)	0.089 (7)	−0.037 (6)	−0.002 (4)	−0.040 (8)
C20	0.059 (3)	0.139 (7)	0.080 (5)	−0.018 (4)	−0.012 (3)	−0.003 (5)

Geometric parameters (Å, º) top

O1—C9	1.425 (7)	C10—H10A	0.9600
O1—H1O	0.8200	C10—H10B	0.9600
O2—C3	1.385 (7)	C10—H10C	0.9600
O2—H2O	0.8200	C11—C12	1.468 (10)
N1—C10	1.482 (7)	C11—H11A	0.9700
N1—C11	1.527 (7)	C11—H11B	0.9700
N1—C14	1.531 (7)	C12—C13	1.317 (3)
N1—C8	1.560 (6)	C12—H12	0.9300
C1—C6	1.387 (9)	C13—H13A	0.9300
C1—C2	1.396 (10)	C13—H13B	0.9300
C1—H1	0.9300	C13'—H13C	0.9300
C2—C3	1.377 (9)	C13'—H13D	0.9300
C2—H2	0.9300	C14—C15	1.495 (8)
C3—C4	1.372 (9)	C14—H14A	0.9700
C4—C5	1.373 (9)	C14—H14B	0.9700
C4—H4	0.9300	C15—C16	1.384 (11)
C5—C6	1.391 (9)	C15—C20	1.388 (10)
C5—H5	0.9300	C16—C17	1.429 (10)
C6—C7	1.487 (8)	C16—H16	0.9300
C7—C8	1.525 (8)	C17—C18	1.367 (17)
C7—H7A	0.9700	C17—H17	0.9300
C7—H7B	0.9700	C18—C19	1.365 (17)
C8—C9	1.520 (8)	C18—H18	0.9300
C8—H8	0.9800	C19—C20	1.361 (13)
C9—H9A	0.9700	C19—H19	0.9300
C9—H9B	0.9700	C20—H20	0.9300

C9—O1—H1O	109.5	N1—C10—H10A	109.5
C3—O2—H2O	109.5	N1—C10—H10B	109.5
C10—N1—C11	106.5 (4)	H10A—C10—H10B	109.5
C10—N1—C14	110.1 (5)	N1—C10—H10C	109.5
C11—N1—C14	109.2 (4)	H10A—C10—H10C	109.5
C10—N1—C8	112.9 (4)	H10B—C10—H10C	109.5
C11—N1—C8	110.0 (4)	C12—C11—N1	114.1 (5)
C14—N1—C8	108.1 (4)	C12—C11—H11A	108.7
C6—C1—C2	121.5 (7)	N1—C11—H11A	108.7
C6—C1—H1	119.2	C12—C11—H11B	108.7
C2—C1—H1	119.2	N1—C11—H11B	108.7
C3—C2—C1	119.1 (6)	H11A—C11—H11B	107.6
C3—C2—H2	120.5	C13—C12—C11	125.0 (9)
C1—C2—H2	120.5	C13—C12—H12	117.5
C4—C3—C2	120.4 (6)	C11—C12—H12	117.5
C4—C3—O2	123.0 (6)	C12—C13—H13A	120.0
C2—C3—O2	116.5 (6)	C12—C13—H13B	120.0
C3—C4—C5	119.8 (6)	H13A—C13—H13B	120.0
C3—C4—H4	120.1	H13C—C13'—H13D	120.0
C5—C4—H4	120.1	C15—C14—N1	116.3 (5)
C4—C5—C6	121.9 (6)	C15—C14—H14A	108.2
C4—C5—H5	119.0	N1—C14—H14A	108.2
C6—C5—H5	119.0	C15—C14—H14B	108.2
C1—C6—C5	117.1 (6)	N1—C14—H14B	108.2
C1—C6—C7	120.8 (6)	H14A—C14—H14B	107.4
C5—C6—C7	122.1 (5)	C16—C15—C20	118.7 (7)
C6—C7—C8	111.6 (5)	C16—C15—C14	118.9 (6)
C6—C7—H7A	109.3	C20—C15—C14	122.2 (7)
C8—C7—H7A	109.3	C15—C16—C17	120.1 (8)
C6—C7—H7B	109.3	C15—C16—H16	120.0
C8—C7—H7B	109.3	C17—C16—H16	120.0
H7A—C7—H7B	108.0	C18—C17—C16	117.2 (10)
C9—C8—C7	110.1 (5)	C18—C17—H17	121.4
C9—C8—N1	113.5 (4)	C16—C17—H17	121.4
C7—C8—N1	112.8 (4)	C19—C18—C17	123.4 (9)
C9—C8—H8	106.7	C19—C18—H18	118.3
C7—C8—H8	106.7	C17—C18—H18	118.3
N1—C8—H8	106.7	C20—C19—C18	118.5 (10)
O1—C9—C8	113.6 (5)	C20—C19—H19	120.7
O1—C9—H9A	108.8	C18—C19—H19	120.7
C8—C9—H9A	108.8	C19—C20—C15	122.0 (10)
O1—C9—H9B	108.8	C19—C20—H20	119.0
C8—C9—H9B	108.8	C15—C20—H20	119.0
H9A—C9—H9B	107.7

C6—C1—C2—C3	1.0 (12)	C7—C8—C9—O1	51.2 (6)
C1—C2—C3—C4	−2.6 (12)	N1—C8—C9—O1	−76.3 (6)
C1—C2—C3—O2	179.8 (7)	C10—N1—C11—C12	175.1 (6)
C2—C3—C4—C5	3.1 (12)	C14—N1—C11—C12	−66.1 (7)
O2—C3—C4—C5	−179.5 (6)	C8—N1—C11—C12	52.5 (7)
C3—C4—C5—C6	−2.0 (11)	N1—C11—C12—C13	−144.3 (12)
C2—C1—C6—C5	0.1 (11)	C10—N1—C14—C15	61.4 (6)
C2—C1—C6—C7	179.2 (6)	C11—N1—C14—C15	−55.1 (7)
C4—C5—C6—C1	0.4 (10)	C8—N1—C14—C15	−174.8 (5)
C4—C5—C6—C7	−178.7 (6)	N1—C14—C15—C16	−93.4 (8)
C1—C6—C7—C8	−98.8 (8)	N1—C14—C15—C20	91.5 (9)
C5—C6—C7—C8	80.4 (8)	C20—C15—C16—C17	−2.0 (12)
C6—C7—C8—C9	65.0 (6)	C14—C15—C16—C17	−177.3 (7)
C6—C7—C8—N1	−167.1 (5)	C15—C16—C17—C18	1.0 (13)
C10—N1—C8—C9	67.4 (6)	C16—C17—C18—C19	0.4 (17)
C11—N1—C8—C9	−173.9 (4)	C17—C18—C19—C20	−0.6 (18)
C14—N1—C8—C9	−54.6 (6)	C18—C19—C20—C15	−0.5 (16)
C10—N1—C8—C7	−58.7 (6)	C16—C15—C20—C19	1.7 (14)
C11—N1—C8—C7	60.0 (6)	C14—C15—C20—C19	176.9 (8)
C14—N1—C8—C7	179.3 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···Br1	0.82	2.43	3.231 (4)	167
O2—H2O···Br1ⁱ	0.82	2.38	3.192 (5)	171

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

Experimental details

Crystal data
Chemical formula	C₂₀H₂₆NO₂⁺·Br⁻
M_r	392.33
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	10.3716 (10), 12.1566 (10), 15.6790 (16)
V (Å³)	1976.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.09
Crystal size (mm)	0.45 × 0.43 × 0.40

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.406, 0.434
No. of measured, independent and observed [I > 2σ(I)] reflections	18872, 4524, 2606
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.211, 1.00
No. of reflections	4524
No. of parameters	225
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.89, −0.69
Absolute structure	Flack (1983), with 1949 Friedel pairs
Absolute structure parameter	0.009 (19)

Computer programs: RAPID-AUTO (Rigaku, 2004), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···Br1	0.82	2.43	3.231 (4)	167.1
O2—H2O···Br1ⁱ	0.82	2.38	3.192 (5)	171.4

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

Acknowledgements

This work was supported financially by the National Natural Science Foundation of China (grant No. 20672108).

References

Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Maruoka, K. & Ooi, T. (2003). Chem. Rev. 103, 3013–3028. Web of Science CrossRef PubMed CAS Google Scholar
Ooi, A. & Maruoka, K. (2007). Angew. Chem. Int. Ed. 46, 4222–4266. Web of Science CrossRef CAS Google Scholar
Rigaku (2004). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tayama, E. & Tanaka, H. (2007). Tetrahedron Lett. 48, 4183–4185. Web of Science CSD CrossRef CAS Google Scholar
White, K. N. & Konopelski, J. P. (2005). Org. Lett. 7, 4111–4112. Web of Science CrossRef PubMed CAS Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(2S,NS)-N-Allyl-N-benzyl-1-hydr­­oxy-3-(4-hy­droxy­phen­yl)-N-methyl­propan-2-aminium bromide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(2S,NS)-N-Allyl-N-benzyl-1-hydroxy-3-(4-hydroxyphenyl)-N-methylpropan-2-aminium bromide