Literature DB >> 21589047

2-Hy-droxy-3-oct-yloxy-N,N,N-trimethyl-propan-1-aminium bromide.

Jiuqiang Liu1, Zengbin Wei, Xilian Wei, Chong Zhang.   

Abstract

In the title compound, C(14)H(32)NO(2) (+)·Br(-), organic cationsstacked parallel to the a axis andbromide anions placed between the head groups of the cations form ionic pairs via weak inter-molecular O-H⋯Br hydrogen bonds. The octyl chain in the cation adopts an all-trans conformation. The O-CH(2)-CH(-OH)-CH(2) portion of the molecule is disordered over two sets of sites with occupancy factors of 0.57 (3) and 0.47 (3).

Entities:  

Year:  2010        PMID： 21589047      PMCID： PMC3009037          DOI： 10.1107/S1600536810040705

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For uses of cationic surfacta­nts, see: Zhao et al. (1997 ▶, 2010 ▶). For bond lengths and angles, see: Koh et al. (1993 ▶).

Experimental

Crystal data

C14H32NO2 +·Br− M = 326.32 Monoclinic, a = 5.9713 (11) Å b = 7.4780 (12) Å c = 19.992 (2) Å β = 92.923 (1)° V = 891.6 (2) Å3 Z = 2 Mo Kα radiation μ = 2.30 mm−1 T = 298 K 0.42 × 0.30 × 0.04 mm

Data collection

Siemens SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.445, T max = 0.914 4642 measured reflections 2827 independent reflections 1168 reflections with I > 2σ(I) R int = 0.135

Refinement

R[F 2 > 2σ(F 2)] = 0.081 wR(F 2) = 0.199 S = 1.03 2827 reflections 211 parameters 1 restraint H-atom parameters constrained Δρmax = 0.74 e Å−3 Δρmin = −0.30 e Å−3 Absolute structure: Flack (1983 ▶), 1124 Friedel pairs Flack parameter: 0.02 (7) 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/S1600536810040705/jj2054sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040705/jj2054Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C14H32NO2+·Br−F(000) = 348
Mr = 326.32Dx = 1.216 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 889 reflections
a = 5.9713 (11) Åθ = 3.1–28.4°
b = 7.4780 (12) ŵ = 2.30 mm−1
c = 19.992 (2) ÅT = 298 K
β = 92.923 (1)°Block, colourless
V = 891.6 (2) Å30.42 × 0.30 × 0.04 mm
Z = 2
Siemens SMART CCD area-detector diffractometer2827 independent reflections
Radiation source: fine-focus sealed tube1168 reflections with I > 2σ(I)
graphiteRint = 0.135
phi and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SABABS; Sheldrick, 1996)h = −7→7
Tmin = 0.445, Tmax = 0.914k = −7→8
4642 measured reflectionsl = −19→23
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.081H-atom parameters constrained
wR(F2) = 0.199w = 1/[σ2(Fo2) + (0.0713P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
2827 reflectionsΔρmax = 0.74 e Å−3
211 parametersΔρmin = −0.30 e Å−3
1 restraintAbsolute structure: Flack (1983), 1124 FRIEDEL PAIRS
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.02 (7)
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.
xyzUiso*/UeqOcc. (<1)
Br10.66822 (19)0.4416 (9)0.40071 (6)0.0909 (6)
N10.0535 (12)0.941 (5)0.3976 (4)0.070 (2)
O1−0.02 (4)0.902 (10)0.186 (9)0.09 (2)0.57 (3)
O2−0.389 (6)1.064 (4)0.3144 (15)0.077 (10)0.57 (3)
H2−0.39151.15800.33560.116*0.57 (3)
C1−0.039 (17)0.883 (12)0.330 (5)0.08 (2)0.57 (3)
H1A−0.13820.78160.33460.099*0.57 (3)
H1B0.08320.84490.30280.099*0.57 (3)
C2−0.168 (12)1.034 (9)0.293 (3)0.079 (16)0.57 (3)
H2A−0.08111.14520.29500.094*0.57 (3)
C3−0.205 (15)0.969 (10)0.221 (4)0.08 (3)0.57 (3)
H3A−0.31760.87560.22110.100*0.57 (3)
H3B−0.26991.06780.19520.100*0.57 (3)
O1'−0.01 (5)0.970 (11)0.192 (12)0.09 (4)0.43 (3)
O2'−0.364 (7)0.801 (5)0.3282 (19)0.077 (13)0.43 (3)
H2'−0.36830.69490.33860.116*0.43 (3)
C1'−0.02 (2)0.979 (13)0.326 (6)0.08 (3)0.43 (3)
H1'10.11200.99540.30080.097*0.43 (3)
H1'2−0.10251.09120.32480.097*0.43 (3)
C2'−0.168 (16)0.834 (12)0.292 (4)0.08 (2)0.43 (3)
H2'1−0.08030.72370.29390.095*0.43 (3)
C3'−0.22 (2)0.870 (17)0.218 (6)0.09 (3)0.43 (3)
H3'1−0.35630.94510.21170.104*0.43 (3)
H3'2−0.25040.75920.19340.104*0.43 (3)
C40.190 (5)1.104 (5)0.4099 (15)0.099 (11)
H4A0.29231.11760.37470.148*
H4B0.27271.09330.45210.148*
H4C0.09321.20640.41070.148*
C50.206 (4)0.784 (5)0.4109 (15)0.096 (10)
H5A0.31870.78220.37830.144*
H5B0.12020.67590.40790.144*
H5C0.27660.79470.45490.144*
C6−0.1293 (12)0.936 (4)0.4460 (4)0.078 (3)
H6A−0.06590.95070.49070.116*
H6B−0.20450.82220.44250.116*
H6C−0.23471.02980.43580.116*
C7−0.0337 (12)0.978 (4)0.1194 (4)0.104 (8)
H7A−0.03551.10790.12190.125*0.57 (3)
H7B−0.16960.93870.09520.125*0.57 (3)
H7C−0.07051.09970.10580.125*0.43 (3)
H7D−0.15880.90230.10520.125*0.43 (3)
C80.169 (2)0.915 (5)0.0850 (6)0.103 (7)
H8A0.29190.99340.09920.123*
H8B0.20560.79730.10250.123*
C90.168 (2)0.903 (4)0.0123 (6)0.112 (9)
H9A0.04340.9736−0.00590.135*
H9B0.13800.77950.00010.135*
C100.375 (2)0.961 (5)−0.0225 (6)0.109 (5)
H10A0.50570.90830.00060.131*
H10B0.38881.0895−0.01930.131*
C110.371 (3)0.907 (5)−0.0954 (6)0.122 (10)
H11A0.33810.7804−0.09830.146*
H11B0.24890.9700−0.11880.146*
C120.581 (2)0.941 (7)−0.1320 (6)0.117 (4)
H12A0.64941.0475−0.11210.141*
H12B0.68180.8427−0.12100.141*
C130.581 (3)0.964 (7)−0.2030 (7)0.131 (8)
H13A0.54961.0895−0.21230.157*
H13B0.45620.8963−0.22260.157*
C140.781 (3)0.916 (7)−0.2394 (8)0.151 (9)
H14A0.91200.9673−0.21710.227*
H14B0.76540.9609−0.28430.227*
H14C0.79590.7882−0.24040.227*
U11U22U33U12U13U23
Br10.0819 (8)0.0684 (8)0.1204 (10)−0.001 (2)−0.0165 (6)0.005 (2)
N10.056 (4)0.076 (6)0.078 (6)0.00 (2)0.007 (5)0.011 (19)
O10.10 (4)0.10 (3)0.08 (4)0.00 (6)0.01 (3)0.01 (5)
O20.067 (18)0.078 (16)0.087 (17)−0.005 (12)0.003 (12)−0.006 (12)
C10.08 (4)0.09 (3)0.07 (5)0.00 (5)0.01 (3)0.01 (5)
C20.08 (4)0.08 (4)0.08 (4)0.00 (3)0.01 (4)0.01 (3)
C30.08 (4)0.09 (8)0.07 (4)0.00 (4)0.00 (3)0.01 (4)
O1'0.10 (6)0.10 (8)0.08 (5)0.00 (8)0.01 (4)0.01 (7)
O2'0.07 (2)0.08 (2)0.09 (2)−0.005 (15)0.003 (17)−0.006 (16)
C1'0.08 (5)0.09 (8)0.07 (6)0.00 (6)0.01 (4)0.01 (6)
C2'0.08 (5)0.09 (6)0.08 (6)0.00 (4)0.01 (5)0.01 (4)
C3'0.09 (5)0.10 (6)0.08 (5)0.00 (6)0.01 (4)0.01 (5)
C40.09 (2)0.10 (3)0.11 (3)−0.015 (18)0.00 (2)0.022 (18)
C50.08 (2)0.09 (3)0.12 (3)0.026 (17)0.010 (19)−0.003 (17)
C60.060 (6)0.103 (9)0.070 (6)0.007 (19)0.008 (5)0.020 (19)
C70.105 (10)0.12 (2)0.084 (10)−0.003 (12)0.005 (8)0.007 (13)
C80.108 (10)0.12 (2)0.078 (9)0.000 (14)0.008 (7)0.011 (14)
C90.119 (11)0.14 (3)0.080 (10)0.000 (13)0.000 (8)0.006 (12)
C100.124 (10)0.128 (15)0.074 (9)−0.01 (2)−0.001 (7)0.016 (17)
C110.127 (12)0.15 (3)0.084 (10)−0.008 (15)0.000 (9)0.004 (13)
C120.133 (11)0.134 (12)0.086 (10)0.00 (4)0.003 (8)0.01 (3)
C130.139 (13)0.16 (2)0.090 (11)0.00 (2)0.005 (9)0.01 (2)
C140.163 (15)0.19 (3)0.098 (11)0.03 (3)0.009 (11)0.01 (2)
N1—C41.48 (4)C5—H5C0.9600
N1—C61.495 (10)C6—H6A0.9600
N1—C1'1.50 (14)C6—H6B0.9600
N1—C51.50 (4)C6—H6C0.9600
N1—C11.51 (11)C7—C81.50 (2)
O1—C31.4 (2)C7—H7A0.9700
O1—C71.44 (17)C7—H7B0.9700
O2—C21.42 (6)C7—H7C0.9703
O2—H20.8200C7—H7D0.9698
C1—C21.53 (12)C8—C91.456 (16)
C1—H1A0.9700C8—H8A0.9700
C1—H1B0.9700C8—H8B0.9700
C2—C31.53 (10)C9—C101.51 (2)
C2—H2A0.9800C9—H9A0.9700
C3—H3A0.9700C9—H9B0.9700
C3—H3B0.9700C10—C111.51 (2)
O1'—C3'1.6 (3)C10—H10A0.9700
O2'—C2'1.43 (7)C10—H10B0.9700
O2'—H2'0.8200C11—C121.501 (19)
C1'—C2'1.54 (16)C11—H11A0.9700
C1'—H1'10.9700C11—H11B0.9700
C1'—H1'20.9700C12—C131.431 (18)
C2'—C3'1.53 (13)C12—H12A0.9700
C2'—H2'10.9800C12—H12B0.9700
C3'—H3'10.9700C13—C141.47 (3)
C3'—H3'20.9700C13—H13A0.9700
C4—H4A0.9600C13—H13B0.9700
C4—H4B0.9600C14—H14A0.9600
C4—H4C0.9600C14—H14B0.9600
C5—H5A0.9600C14—H14C0.9600
C5—H5B0.9600
C4—N1—C6109 (3)H6A—C6—H6C109.5
C4—N1—C1'98 (5)H6B—C6—H6C109.5
C6—N1—C1'116 (5)O1'—C7—O121 (5)
C4—N1—C5106.9 (8)O1'—C7—C8114 (10)
C6—N1—C5109 (2)O1—C7—C8107 (8)
C1'—N1—C5118 (5)O1'—C7—H7A89.5
C4—N1—C1124 (4)O1—C7—H7A110.4
C6—N1—C1109 (4)C8—C7—H7A110.4
C1'—N1—C128 (3)O1'—C7—H7B121.5
C5—N1—C197 (4)O1—C7—H7B110.4
C3—O1—C7108 (10)C8—C7—H7B110.4
C2—O2—H2109.5H7A—C7—H7B108.6
N1—C1—C2112 (7)O1'—C7—H7C109.2
N1—C1—H1A109.3O1—C7—H7C129.1
C2—C1—H1A109.3C8—C7—H7C110.0
N1—C1—H1B109.3H7A—C7—H7C22.6
C2—C1—H1B109.3H7B—C7—H7C88.5
H1A—C1—H1B108.0O1'—C7—H7D107.7
O2—C2—C3104 (6)O1—C7—H7D92.8
O2—C2—C1115 (5)C8—C7—H7D108.0
C3—C2—C1105 (6)H7A—C7—H7D126.2
O2—C2—H2A110.7H7B—C7—H7D20.3
C3—C2—H2A110.7H7C—C7—H7D107.8
C1—C2—H2A110.8C9—C8—C7121.2 (14)
O1—C3—C2120 (9)C9—C8—H8A107.0
O1—C3—H3A107.4C7—C8—H8A107.0
C2—C3—H3A107.4C9—C8—H8B107.0
O1—C3—H3B107.4C7—C8—H8B107.0
C2—C3—H3B107.4H8A—C8—H8B106.8
H3A—C3—H3B106.9C8—C9—C10118.8 (16)
C7—O1'—C3'108 (10)C8—C9—H9A107.6
C2'—O2'—H2'109.5C10—C9—H9A107.6
N1—C1'—C2'115 (8)C8—C9—H9B107.6
N1—C1'—H1'1108.4C10—C9—H9B107.6
C2'—C1'—H1'1108.4H9A—C9—H9B107.0
N1—C1'—H1'2108.4C9—C10—C11113.5 (19)
C2'—C1'—H1'2108.4C9—C10—H10A108.9
H1'1—C1'—H1'2107.5C11—C10—H10A108.9
O2'—C2'—C3'113 (8)C9—C10—H10B108.9
O2'—C2'—C1'111 (7)C11—C10—H10B108.9
C3'—C2'—C1'114 (8)H10A—C10—H10B107.7
O2'—C2'—H2'1106.3C12—C11—C10117.1 (18)
C3'—C2'—H2'1106.3C12—C11—H11A108.0
C1'—C2'—H2'1106.3C10—C11—H11A108.0
C2'—C3'—O1'105 (10)C12—C11—H11B108.0
C2'—C3'—H3'1110.7C10—C11—H11B108.0
O1'—C3'—H3'1110.7H11A—C11—H11B107.3
C2'—C3'—H3'2110.7C13—C12—C11123.2 (13)
O1'—C3'—H3'2110.7C13—C12—H12A106.5
H3'1—C3'—H3'2108.8C11—C12—H12A106.5
N1—C4—H4A109.5C13—C12—H12B106.5
N1—C4—H4B109.5C11—C12—H12B106.5
H4A—C4—H4B109.5H12A—C12—H12B106.5
N1—C4—H4C109.5C12—C13—C14120 (2)
H4A—C4—H4C109.5C12—C13—H13A107.3
H4B—C4—H4C109.5C14—C13—H13A107.3
N1—C5—H5A109.5C12—C13—H13B107.3
N1—C5—H5B109.5C14—C13—H13B107.3
H5A—C5—H5B109.5H13A—C13—H13B106.9
N1—C5—H5C109.5C13—C14—H14A109.5
H5A—C5—H5C109.5C13—C14—H14B109.5
H5B—C5—H5C109.5H14A—C14—H14B109.5
N1—C6—H6A109.5C13—C14—H14C109.5
N1—C6—H6B109.5H14A—C14—H14C109.5
H6A—C6—H6B109.5H14B—C14—H14C109.5
N1—C6—H6C109.5
C4—N1—C1—C2−52 (8)N1—C1'—C2'—C3'−175 (8)
C6—N1—C1—C280 (7)O2'—C2'—C3'—O1'160 (9)
C1'—N1—C1—C2−29 (12)C1'—C2'—C3'—O1'33 (14)
C5—N1—C1—C2−168 (6)C7—O1'—C3'—C2'169 (9)
N1—C1—C2—O2−78 (9)C3'—O1'—C7—C8−130 (11)
N1—C1—C2—C3168 (6)C3—O1—C7—C8177 (7)
C7—O1—C3—C2−136 (8)O1'—C7—C8—C9176 (6)
O2—C2—C3—O1−172 (8)O1—C7—C8—C9155 (6)
C1—C2—C3—O1−50 (11)C7—C8—C9—C10140 (3)
C4—N1—C1'—C2'179 (8)C8—C9—C10—C11168 (3)
C6—N1—C1'—C2'−66 (10)C9—C10—C11—C12−173 (3)
C5—N1—C1'—C2'65 (10)C10—C11—C12—C13−155 (4)
C1—N1—C1'—C2'17 (11)C11—C12—C13—C14−152 (4)
N1—C1'—C2'—O2'57 (12)
D—H···AD—HH···AD···AD—H···A
O2—H2···Br1i0.822.503.32 (3)171
O2'—H2'···Br1ii0.822.273.05 (4)160
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O2—H2⋯Br1i0.822.503.32 (3)171
O2′—H2′⋯Br1ii0.822.273.05 (4)160

Symmetry codes: (i) ; (ii) .

  2 in total

1.  Enhanced soil retention for o-nitroaniline by the addition of a mixture of a cationic surfactant (Cetyl Pyridinium Chloride) and a nonionic surfactant (Polyethylene Glycol Mono-4-nonylphenyl Ether).

Authors:  Qing Zhao; Kun Yang; Peijun Li
Journal:  J Hazard Mater       Date:  2010-06-30       Impact factor: 10.588

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290
  2 in total
  1 in total

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

Authors:  Xiuhong Wang; Xilian Wei; Panpan Du
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-12-23
  1 in total

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