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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

3-Dodec­yl­oxy-2-hydr­­oxy-N,N,N-tri­methyl­propan-1-aminium bromide

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

(Received 23 May 2009; accepted 7 July 2009; online 11 July 2009)

In the title compound, C18H40NO2+·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 trimethyl­aminium 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[Koh, L. L., Xu, Y., Gan, L. M., Chew, C. H. & Lee, K. C. (1993). Acta Cryst. C49, 1032-1035.]). For applications of 3-alk­oxy-2-hydroxy­propyl-N,N,N-trimethyl­propan-1-amin­ium bromides, see: Yin et al. (2001[Yin, B., Sun, D., Wei, X., Wang, Y., Zhao, S. & Zheng, X. (2001). J. Solution Chem. 30, 895-908.]); Zhao et al. (1997[Zhao, S. Y., Zhang, G. Y., Zheng, G. X. & Niu, C. Z. (1997). China Surfact. Deterg. Cosmet. 5, 7-9.]).

[Scheme 1]

Experimental

Crystal data
  • C18H40NO2+·Br

  • Mr = 382.42

  • Monoclinic, P 21

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.474, Tmax = 0.689

  • 5077 measured reflections

  • 3431 independent reflections

  • 1751 reflections with I > 2σ(I)

  • Rint = 0.081

Refinement
  • R[F2 > 2σ(F2)] = 0.063

  • wR(F2) = 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[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1274 Friedel pairs

  • Flack parameter: 0.33 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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) x-1, y, z; (ii) [-x+2, y-{\script{1\over 2}}, -z+1].

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

3-Alkoxy-2-hydroxypropyl-N,N,N-trimethylpropan-1-aminium bromides (RTABs) are a new type of cationic surfactants (Yin et al., 2001).They are used as bacteriocides, emulgents, antistatic agents and pigment-dispersing agents in a variety of industries, such as in the production of cosmetics, pharmaceuticals, and textiles (Zhao et al., 1997). As a contribution to the chemistry of surfactants, we report here the synthesis and crystal structure of the title compound. The asymmetric unit of the title compound (Fig. 1), consists of a 3-dodecyloxy-2-hydroxypropyl-N,N,N- trimethylpropan-1-aminium cations, and a bromide anion. The dodecyl chains of the cations are arranged parallel in one layer and antiparallel in alternate layers, and the C—C—C angles tend to be larger towards the end of the chain. The bond lengths of C3—O2 and C7—O2 are 1.459 (11) and 1.369 (9) Å, respectively. All N—C bond lengths and C—N—C angles are within the usual ranges (Koh et al., 1993). In the crystal, the cations are stacked parallel along the a axis (Fig. 2). 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 interactions (Table 1).

Related literature top

For related crystal 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 top

The reaction was carried out under nitrogen atmosphere. Trimethylammonium bromide (0.12 mol) and dodecyl glycidyl 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. Colourless crystals suitable for X-ray analysis were obtained by slow evaporation of a ethyl acetate solution over a period of two weeks. (yield 81%, m.p. 342Kk) Anal. Calcd (%) for C18H40Br1N1O2 (Mr = 382.42): C, 56.48; H, 10.46; N, 3.66. Found (%): C, 56.43; H, 10.50; N, 3.63.

Refinement top

All H atoms were placed geometrically and treated as riding on their parent atoms with O—H = 0.82 Å, C—H = 0.97 (methylene) Å [Uiso(H) = 1.2Ueq(C)], and C—H = 0.96 (methyl) Å [Uiso(H) = 1.5Ueq(C)]. The crystal was refined as a racemic twin with the 0.33 (3)/0.67 (3) ratio of the twin domains.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom labels and 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. Crystal packing of the title compound, showing one extended chain structure, linked by O—H···Br and C—H···O hydrogen bonds (dashed lines).
3-Dodecyloxy-2-hydroxy-N,N,N-trimethylpropan-1-aminium bromide top
Crystal data top
C18H40NO2+·BrF(000) = 412
Mr = 382.42Dx = 1.125 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 1870 reflections
a = 6.0476 (11) Åθ = 2.5–21.7°
b = 7.5370 (12) ŵ = 1.83 mm1
c = 24.870 (2) ÅT = 298 K
β = 94.974 (1)°Block, colorless
V = 1129.3 (3) Å30.48 × 0.34 × 0.22 mm
Z = 2
Data collection top
Bruker SMART
diffractometer
3431 independent reflections
Radiation source: fine-focus sealed tube1751 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.081
Detector resolution: 0 pixels mm-1θmax = 25.0°, θmin = 3.2°
ϕ and ω scansh = 57
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 88
Tmin = 0.474, Tmax = 0.689l = 2729
5077 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.063H-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 reflectionsΔρmax = 0.54 e Å3
204 parametersΔρmin = 0.57 e Å3
1 restraintAbsolute structure: Flack (1983), 1274 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.33 (3)
Crystal data top
C18H40NO2+·BrV = 1129.3 (3) Å3
Mr = 382.42Z = 2
Monoclinic, P21Mo Kα radiation
a = 6.0476 (11) ŵ = 1.83 mm1
b = 7.5370 (12) ÅT = 298 K
c = 24.870 (2) Å0.48 × 0.34 × 0.22 mm
β = 94.974 (1)°
Data collection top
Bruker SMART
diffractometer
3431 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1751 reflections with I > 2σ(I)
Tmin = 0.474, Tmax = 0.689Rint = 0.081
5077 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.063H-atom parameters constrained
wR(F2) = 0.158Δρmax = 0.54 e Å3
S = 1.00Δρmin = 0.57 e Å3
3431 reflectionsAbsolute structure: Flack (1983), 1274 Friedel pairs
204 parametersAbsolute structure parameter: 0.33 (3)
1 restraint
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.21650 (16)0.2943 (2)0.08166 (3)0.0752 (4)
N11.3970 (9)0.297 (2)0.91650 (19)0.0510 (15)
O11.7912 (10)0.1699 (9)0.8526 (2)0.0742 (18)
H11.79440.08360.87270.089*
O21.3595 (12)0.2556 (13)0.7440 (2)0.095 (4)
C11.4538 (16)0.337 (3)0.8576 (3)0.105 (8)
H1A1.31630.36360.83620.126*
H1B1.54460.44290.85850.126*
C21.5697 (15)0.1972 (15)0.8294 (3)0.069 (3)
H21.48550.08600.82830.083*
C31.5831 (17)0.274 (3)0.7705 (3)0.118 (5)
H3A1.62800.39760.77190.142*
H3B1.68880.20720.75140.142*
C41.5977 (11)0.294 (3)0.9561 (2)0.063 (2)
H4A1.67330.40620.95510.095*
H4B1.69550.20100.94680.095*
H4C1.55320.27430.99170.095*
C51.266 (2)0.467 (2)0.9240 (5)0.070 (5)
H5A1.36770.56310.93230.105*
H5B1.17360.45150.95300.105*
H5C1.17580.49310.89130.105*
C61.254 (2)0.144 (2)0.9272 (5)0.081 (5)
H6A1.23390.13940.96500.122*
H6B1.32370.03670.91660.122*
H6C1.11290.15740.90690.122*
C71.3494 (19)0.260 (3)0.6888 (3)0.111 (6)
H7A1.42360.15540.67670.133*
H7B1.43350.36240.67840.133*
C81.1261 (17)0.269 (3)0.6594 (3)0.100 (4)
H8A1.03730.34780.67960.120*
H8B1.06100.15180.66110.120*
C91.095 (2)0.329 (3)0.5998 (4)0.126 (6)
H9A1.10880.45710.59860.151*
H9B1.21510.27940.58100.151*
C100.8776 (18)0.277 (3)0.5696 (3)0.111 (4)
H10A0.75850.32640.58860.133*
H10B0.86450.14880.57110.133*
C110.841 (2)0.333 (4)0.5107 (3)0.130 (7)
H11A0.87690.45840.50930.156*
H11B0.95030.27100.49150.156*
C120.626 (2)0.309 (4)0.4796 (3)0.132 (5)
H12A0.57710.19090.48800.158*
H12B0.52510.39070.49510.158*
C130.585 (2)0.328 (4)0.4222 (3)0.139 (8)
H13A0.69860.25890.40640.167*
H13B0.61440.45130.41410.167*
C140.3699 (19)0.282 (3)0.3913 (3)0.121 (4)
H14A0.35020.15470.39470.145*
H14B0.25330.33790.40970.145*
C150.3272 (18)0.326 (4)0.3326 (3)0.129 (7)
H15A0.34280.45310.32900.155*
H15B0.44450.27140.31400.155*
C160.1111 (19)0.274 (3)0.3030 (3)0.120 (5)
H16A0.08890.14910.31030.143*
H16B0.00430.33800.31970.143*
C170.069 (2)0.298 (4)0.2446 (4)0.175 (8)
H17A0.10650.42040.23700.210*
H17B0.17440.22430.22790.210*
C180.147 (2)0.265 (4)0.2162 (4)0.171 (10)
H18A0.17910.14000.21710.257*
H18B0.14650.30270.17940.257*
H18C0.25890.32900.23330.257*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0807 (6)0.0495 (5)0.0990 (6)0.0305 (7)0.0278 (4)0.0123 (8)
N10.037 (3)0.066 (4)0.050 (3)0.013 (7)0.005 (3)0.003 (8)
O10.068 (4)0.069 (4)0.086 (4)0.001 (4)0.005 (3)0.006 (3)
O20.138 (6)0.115 (10)0.030 (3)0.065 (7)0.003 (3)0.010 (4)
C10.065 (6)0.20 (2)0.047 (5)0.023 (11)0.010 (5)0.007 (9)
C20.052 (6)0.088 (7)0.067 (7)0.006 (5)0.002 (5)0.008 (6)
C30.107 (8)0.210 (16)0.039 (5)0.002 (16)0.006 (5)0.039 (12)
C40.047 (4)0.085 (6)0.054 (4)0.023 (9)0.010 (4)0.032 (9)
C50.072 (9)0.056 (9)0.083 (10)0.046 (7)0.007 (8)0.001 (6)
C60.053 (9)0.070 (10)0.119 (13)0.016 (7)0.001 (8)0.037 (9)
C70.115 (8)0.152 (18)0.066 (6)0.051 (12)0.012 (6)0.014 (9)
C80.124 (9)0.115 (12)0.059 (6)0.018 (11)0.000 (5)0.013 (9)
C90.157 (11)0.166 (19)0.053 (5)0.010 (14)0.003 (6)0.010 (10)
C100.133 (9)0.134 (12)0.063 (6)0.020 (14)0.006 (6)0.016 (11)
C110.145 (10)0.20 (2)0.046 (6)0.005 (14)0.002 (6)0.008 (10)
C120.162 (10)0.178 (14)0.048 (6)0.035 (18)0.025 (6)0.010 (14)
C130.135 (10)0.22 (2)0.053 (6)0.046 (16)0.019 (6)0.015 (12)
C140.147 (10)0.152 (12)0.062 (6)0.021 (17)0.002 (6)0.022 (13)
C150.120 (9)0.205 (19)0.060 (6)0.046 (15)0.001 (6)0.006 (11)
C160.141 (10)0.148 (14)0.069 (6)0.042 (15)0.002 (6)0.004 (12)
C170.140 (11)0.31 (2)0.069 (7)0.02 (2)0.001 (7)0.118 (16)
C180.179 (13)0.26 (3)0.073 (7)0.12 (2)0.012 (8)0.005 (15)
Geometric parameters (Å, º) top
N1—C61.48 (2)C9—C101.510 (16)
N1—C41.496 (7)C9—H9A0.9700
N1—C51.524 (18)C9—H9B0.9700
N1—C11.561 (10)C10—C111.521 (14)
O1—C21.426 (10)C10—H10A0.9700
O1—H10.8200C10—H10B0.9700
O2—C71.369 (9)C11—C121.463 (16)
O2—C31.459 (11)C11—H11A0.9700
C1—C21.475 (18)C11—H11B0.9700
C1—H1A0.9700C12—C131.435 (11)
C1—H1B0.9700C12—H12A0.9700
C2—C31.584 (14)C12—H12B0.9700
C2—H20.9800C13—C141.495 (15)
C3—H3A0.9700C13—H13A0.9700
C3—H3B0.9700C13—H13B0.9700
C4—H4A0.9600C14—C151.496 (13)
C4—H4B0.9600C14—H14A0.9700
C4—H4C0.9600C14—H14B0.9700
C5—H5A0.9600C15—C161.495 (15)
C5—H5B0.9600C15—H15A0.9700
C5—H5C0.9600C15—H15B0.9700
C6—H6A0.9600C16—C171.465 (13)
C6—H6B0.9600C16—H16A0.9700
C6—H6C0.9600C16—H16B0.9700
C7—C81.481 (13)C17—C181.452 (15)
C7—H7A0.9700C17—H17A0.9700
C7—H7B0.9700C17—H17B0.9700
C8—C91.544 (13)C18—H18A0.9600
C8—H8A0.9700C18—H18B0.9600
C8—H8B0.9700C18—H18C0.9600
C6—N1—C4109.0 (12)C8—C9—H9A108.4
C6—N1—C5108.4 (6)C10—C9—H9B108.4
C4—N1—C5109.3 (11)C8—C9—H9B108.4
C6—N1—C1119.8 (11)H9A—C9—H9B107.5
C4—N1—C1112.8 (6)C9—C10—C11117.0 (13)
C5—N1—C196.4 (11)C9—C10—H10A108.0
C2—O1—H1109.5C11—C10—H10A108.0
C7—O2—C3114.2 (8)C9—C10—H10B108.0
C2—C1—N1117.5 (15)C11—C10—H10B108.0
C2—C1—H1A107.9H10A—C10—H10B107.3
N1—C1—H1A107.9C12—C11—C10121.6 (13)
C2—C1—H1B107.9C12—C11—H11A106.9
N1—C1—H1B107.9C10—C11—H11A106.9
H1A—C1—H1B107.2C12—C11—H11B106.9
O1—C2—C1112.3 (8)C10—C11—H11B106.9
O1—C2—C3107.7 (8)H11A—C11—H11B106.7
C1—C2—C3104.2 (12)C13—C12—C11125.7 (12)
O1—C2—H2110.8C13—C12—H12A105.9
C1—C2—H2110.8C11—C12—H12A105.9
C3—C2—H2110.8C13—C12—H12B105.9
O2—C3—C2105.3 (9)C11—C12—H12B105.9
O2—C3—H3A110.7H12A—C12—H12B106.2
C2—C3—H3A110.7C12—C13—C14123.8 (12)
O2—C3—H3B110.7C12—C13—H13A106.4
C2—C3—H3B110.7C14—C13—H13A106.4
H3A—C3—H3B108.8C12—C13—H13B106.4
N1—C4—H4A109.5C14—C13—H13B106.4
N1—C4—H4B109.5H13A—C13—H13B106.4
H4A—C4—H4B109.5C15—C14—C13121.3 (12)
N1—C4—H4C109.5C15—C14—H14A107.0
H4A—C4—H4C109.5C13—C14—H14A107.0
H4B—C4—H4C109.5C15—C14—H14B107.0
N1—C5—H5A109.5C13—C14—H14B107.0
N1—C5—H5B109.5H14A—C14—H14B106.8
H5A—C5—H5B109.5C16—C15—C14119.5 (13)
N1—C5—H5C109.5C16—C15—H15A107.5
H5A—C5—H5C109.5C14—C15—H15A107.5
H5B—C5—H5C109.5C16—C15—H15B107.5
N1—C6—H6A109.5C14—C15—H15B107.5
N1—C6—H6B109.5H15A—C15—H15B107.0
H6A—C6—H6B109.5C17—C16—C15121.7 (13)
N1—C6—H6C109.5C17—C16—H16A106.9
H6A—C6—H6C109.5C15—C16—H16A106.9
H6B—C6—H6C109.5C17—C16—H16B106.9
O2—C7—C8117.2 (9)C15—C16—H16B106.9
O2—C7—H7A108.0H16A—C16—H16B106.7
C8—C7—H7A108.0C18—C17—C16122.2 (14)
O2—C7—H7B108.0C18—C17—H17A106.8
C8—C7—H7B108.0C16—C17—H17A106.8
H7A—C7—H7B107.3C18—C17—H17B106.8
C7—C8—C9121.1 (11)C16—C17—H17B106.8
C7—C8—H8A107.1H17A—C17—H17B106.6
C9—C8—H8A107.0C17—C18—H18A109.5
C7—C8—H8B107.1C17—C18—H18B109.5
C9—C8—H8B107.1H18A—C18—H18B109.5
H8A—C8—H8B106.8C17—C18—H18C109.5
C10—C9—C8115.4 (13)H18A—C18—H18C109.5
C10—C9—H9A108.4H18B—C18—H18C109.5
C6—N1—C1—C259.5 (13)C7—C8—C9—C10161.0 (19)
C4—N1—C1—C270.9 (17)C8—C9—C10—C11179.9 (18)
C5—N1—C1—C2175.0 (11)C9—C10—C11—C12172 (2)
N1—C1—C2—O168.1 (13)C10—C11—C12—C13168 (2)
N1—C1—C2—C3175.6 (10)C11—C12—C13—C14172 (3)
C7—O2—C3—C2160.1 (15)C12—C13—C14—C15172 (2)
O1—C2—C3—O2165.6 (11)C13—C14—C15—C16179 (2)
C1—C2—C3—O275.0 (16)C14—C15—C16—C17174 (2)
C3—O2—C7—C8171.2 (18)C15—C16—C17—C18174 (3)
O2—C7—C8—C9162.0 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6C···O1i0.962.273.229 (13)174
O1—H1···Br1ii0.822.463.272 (6)170
Symmetry codes: (i) x1, y, z; (ii) x+2, y1/2, z+1.

Experimental details

Crystal data
Chemical formulaC18H40NO2+·Br
Mr382.42
Crystal system, space groupMonoclinic, P21
Temperature (K)298
a, b, c (Å)6.0476 (11), 7.5370 (12), 24.870 (2)
β (°) 94.974 (1)
V3)1129.3 (3)
Z2
Radiation typeMo Kα
µ (mm1)1.83
Crystal size (mm)0.48 × 0.34 × 0.22
Data collection
DiffractometerBruker SMART
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.474, 0.689
No. of measured, independent and
observed [I > 2σ(I)] reflections
5077, 3431, 1751
Rint0.081
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.158, 1.00
No. of reflections3431
No. of parameters204
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.54, 0.57
Absolute structureFlack (1983), 1274 Friedel pairs
Absolute structure parameter0.33 (3)

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6C···O1i0.962.273.229 (13)174
O1—H1···Br1ii0.822.463.272 (6)170
Symmetry codes: (i) x1, y, z; (ii) x+2, y1/2, z+1.
 

Acknowledgements

We acknowledge financial support by the National Natural Science Foundation of China (20673050) and the Shandong Province Science Foundation (2006B05).

References

First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationKoh, 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
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar
First citationYin, B., Sun, D., Wei, X., Wang, Y., Zhao, S. & Zheng, X. (2001). J. Solution Chem. 30, 895–908.  Web of Science CrossRef CAS Google Scholar
First citationZhao, S. Y., Zhang, G. Y., Zheng, G. X. & Niu, C. Z. (1997). China Surfact. Deterg. Cosmet. 5, 7–9.  Google Scholar

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