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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 10| October 2011| Page o2553
https://doi.org/10.1107/S1600536811035410

2-Phenyl-3-(tri­methyl­sil­yl)propan-1-aminium chloride

Yousef M. Hijji,a Ray J. Butcher,b* Jerry P. Jasinski,c Zachary Whiteb and Robert C. Rosenbergb

aChemistry Department, Morgan State University, 1700 East Cold Spring Lane, Baltimore, MD 21251, USA, bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, and cDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
*Correspondence e-mail: rbutcher99@yahoo.com

(Received 26 August 2011; accepted 30 August 2011; online 3 September 2011)

The title compound, C12H22NSi+·Cl−, contains two formula units in the asymmetric unit and is a hydro­chloride salt in which the amine N atom is protonated and the NH3+ group forms hydrogen bonds with the Cl− anion, forming a ribbon in the c-axis direction.

Related literature

For silicon-substituted β-phenyl­ethyl amine and its biological activity, see: Frankel et al. (1968[Frankel, M., Broze, M., Gertner, D., Rotman, A., Shenhar, A. & Zilkha, A. (1968). J. Med. Chem. 11, 857-860.]). For applications of β-phenyl­ethyl amine in alkaloid synthesis via the Pictet–Spengler reaction, see: Lorenz et al. (2010[Lorenz, M., Linn, M. L. V. & Cook, J. M. (2010). Curr. Org. Synth. 7, 189-223.]). For uses and applications of 3-amino-propyl­silanes in nano technology and self-assembled monolayers, see: Li et al. (2009[Li, J.-R., Lusker, K. L., Yu, J.-J. & Garno, J. C. (2009). ACS Nano, 3, 2023-2035.]) and in reverse ionic liquids in oil extraction, see: Blasucci et al. (2010[Blasucci, V., Hart, R., Mestre, V. L., Hahne, D. J., Burlager, M., Huttenhower, H., Thio, B. J. R., Pollet, P., Liotta, C. L. & Eckert, C. A. (2010). Fuel, 89, 1315-1319.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data

  • C12H22NSi+·Cl−

  • Mr = 243.85

  • Monoclinic, P 21 /c

  • a = 12.3716 (4) Å

  • b = 32.6920 (8) Å

  • c = 7.44256 (18) Å

  • β = 93.006 (2)°

  • V = 3006.01 (14) Å3

  • Z = 8

  • Cu Kα radiation

  • μ = 2.79 mm−1

  • T = 295 K

  • 0.47 × 0.10 × 0.06 mm
Data collection

  • Oxford Diffraction Xcalibur Ruby Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.370, Tmax = 1.000

  • 11195 measured reflections

  • 5882 independent reflections

  • 3078 reflections with I > 2σ(I)

  • Rint = 0.049
Refinement

  • R[F2 > 2σ(F2)] = 0.076

  • wR(F2) = 0.276

  • S = 1.14

  • 5882 reflections

  • 279 parameters

  • H-atom parameters constrained

  • Δρmax = 0.72 e Å−3

  • Δρmin = −0.49 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1A—H1AA⋯Cl2i 0.89 2.23 3.114 (5) 173
N1A—H1AB⋯Cl1 0.89 2.25 3.136 (4) 172
N1A—H1AC⋯Cl1ii 0.89 2.36 3.168 (5) 152
N1B—H1BA⋯Cl2ii 0.89 2.30 3.166 (4) 163
N1B—H1BB⋯Cl2 0.89 2.28 3.165 (4) 171
N1B—H1BC⋯Cl1 0.89 2.35 3.222 (5) 165
Symmetry codes: (i) x, y, z+1; (ii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811035410/hg5087sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811035410/hg5087Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811035410/hg5087Isup3.cml

checkCIF report


Comment top

The title compound is a substituted α-phenyethylaminium chloride. Phenylethyl amines are substrates for dopamine-β-hydroxylase and are of biological importance. Silicon substituted phenylethyl amines have been investigated for biological activity and use as insecticide and applications in pharmaceuticals (Frankel et al. 1968). Viewing these compounds as substituted 3-silylpropylamine where they have application in monolayer construction and nanotechnology (Li et al. 2009) and use in oil recovery via reverse ionic liquids (Blasucci et al., 2010). Phenylethyl amines are important building blocks in isoquinoline alkaloid synthesis via Pictet–Spengler (Lorenz et al. 2010).

In view of the importance of these compounds the structure of 2-phenyl-3-(trimethylsilyl)-propan-l-aminium chloride, C12H22ClNSi is reported. The title compound contains two formula units in the asymmetric unit and is a hydrochloride salt where the amine N is protonated and the NH3+ group forms hydrogen bonds with the Cl- anion. These hydrogen bonds form a ribbon in the c direction. The metrical parameters for the salt are in the normal range (Allen, 2002).

Related literature top

For silicon-substituted β-phenylethyl amine and its biological activity, see: Frankel et al. (1968). For applications of β-phenylethyl amine in alkaloid synthesis via Pictet–Spengler reaction, see: Lorenz et al. (2010). For uses and applications of 3-amino-propylsilanes in nano technology and self-assembled monolayers, see: Li et al. (2009) and in reverse ionic liquids in oil extraction, see: Blasucci et al. (2010). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental top

To 5.20 g (44.4 mmol) benzylnitrile in 40 ml of dry THF under nitrogen atmosphere, cooled in an ice bath was added 28.0 ml of n-Bu Li (1.6 M) (44.8 mmol) dropwise. After the addition was complete the solution turned to a creamy slurry. The mixture was stirred for 10 minutes then the ice bath was removed and 5.54 g of chloromethyltrimethyl silane (6.3 ml) was added dropwise. After the addition was complete the mixture was stirred for 2 h at room temperature. The reaction was worked up by water addition and extraction with ether twice (25 ml). The organic layers were combined and washed with saturated NaCl solution, dried (MgSO4). The solvent was removed to give 3-trimethylsilyl-2-phenyl-propionitrile, as yellowish liquid 7.5 g (78%). 2.0 g of 3-trimethylsilyl-2-phenyl-propionitrile were dissolved in 5 ml of dry THF and heated to 343 K in a distillation set up. 3.0 ml of BH3.DMS (10 M) was added dropwise over a period of 10 minutes. Dimethylsulfide (DMS) distilled off the reaction mixture and was collected in the receiver. The mixture was heated for 15 minutes then cooled to room temperature. A reflux condenser was connected to the reaction flask and 10 ml of 6 M HCl was added carefully and slowly. After the addition was complete and no more gas evolved the mixture was heated for 30 minutes at reflux. The reaction mixture was cooled to room temperature, transferred to a beaker. KOH pellets were added slowly to the solution to neutralize the acid. The mixture was extracted with 2x25 ml of ether. The organic layers were combined and 5 ml of concentrated HCl was added. The aqueous layer was allowed to evaporate to give white solid. The solid was washed with ether and filtered to give 0.98 g (41%) of the title compound. A sample was dissolved in water and allowed to evaporate slowly to give clear crystals of the title compound used for x-ray crystallography.

1H NMR (DMSO-d6, 400 MHz): δ (p.p.m.) = 7.85 (br, 3H), 7.31 (m, 5H), 2.94 (m,3H), 1.00 (dd,1H, J= 14.5, 3.5 Hz), 0.92 (dd, 1 H, J = 14.5, 11 Hz), -0.28 (s, 9H). 13C NMR (DMSO-d6,, 100 MHz): δ (p.p.m.) 142.24, 128.65, 127.91, 127.16, 46.89, 39.78, 21.01, -1.21. Exact Mass = 207.084401 (M+ - HCl) Mass Spec (EI) direct probe M/z: 208 (M—Cl), 192 (M+ –NH2Cl), 177 (M—CH2NH3Cl), 147, 121, 104, 91, 73 (base).

Refinement top

H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with a C—H distances of 0.93 to 0.97 Å and N—H distances of 0.89 Å and Uiso(H) = 1.2Ueq(C, N).

Structure description top

The title compound is a substituted α-phenyethylaminium chloride. Phenylethyl amines are substrates for dopamine-β-hydroxylase and are of biological importance. Silicon substituted phenylethyl amines have been investigated for biological activity and use as insecticide and applications in pharmaceuticals (Frankel et al. 1968). Viewing these compounds as substituted 3-silylpropylamine where they have application in monolayer construction and nanotechnology (Li et al. 2009) and use in oil recovery via reverse ionic liquids (Blasucci et al., 2010). Phenylethyl amines are important building blocks in isoquinoline alkaloid synthesis via Pictet–Spengler (Lorenz et al. 2010).

In view of the importance of these compounds the structure of 2-phenyl-3-(trimethylsilyl)-propan-l-aminium chloride, C12H22ClNSi is reported. The title compound contains two formula units in the asymmetric unit and is a hydrochloride salt where the amine N is protonated and the NH3+ group forms hydrogen bonds with the Cl- anion. These hydrogen bonds form a ribbon in the c direction. The metrical parameters for the salt are in the normal range (Allen, 2002).

For silicon-substituted β-phenylethyl amine and its biological activity, see: Frankel et al. (1968). For applications of β-phenylethyl amine in alkaloid synthesis via Pictet–Spengler reaction, see: Lorenz et al. (2010). For uses and applications of 3-amino-propylsilanes in nano technology and self-assembled monolayers, see: Li et al. (2009) and in reverse ionic liquids in oil extraction, see: Blasucci et al. (2010). For a description of the Cambridge Structural Database, see: Allen (2002).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); 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. Diagram of C12H22ClNSi, showing the contents of the asymmetric unit. Hydrogen bonds are shown by dashed lines (30% atomic displacement parameters).
[Figure 2] Fig. 2. The molecular packing for C12H22ClNSi, viewed down the a axis showing the hydogen bonded ribbons in the c direction. Hydrogen bonds are shown by dashed lines.
2-Phenyl-3-(trimethylsilyl)propan-1-aminium chloride top
Crystal data top
C12H22NSi+·Cl−F(000) = 1056
Mr = 243.85Dx = 1.078 Mg m−3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybcCell parameters from 3131 reflections
a = 12.3716 (4) Åθ = 4.5–75.7°
b = 32.6920 (8) ŵ = 2.79 mm−1
c = 7.44256 (18) ÅT = 295 K
β = 93.006 (2)°Needle, colorless
V = 3006.01 (14) Å30.47 × 0.10 × 0.06 mm
Z = 8
Data collection top
Oxford Diffraction Xcalibur Ruby Gemini
diffractometer		5882 independent reflections
Radiation source: Enhance (Cu) X-ray Source3078 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
Detector resolution: 10.5081 pixels mm-1θmax = 76.0°, θmin = 4.5°
ω scansh = −15→15
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)		k = −40→38
Tmin = 0.370, Tmax = 1.000l = −9→8
11195 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.076Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.276H-atom parameters constrained
S = 1.14 w = 1/[σ2(Fo2) + (0.1129P)2 + 1.1585P]
where P = (Fo2 + 2Fc2)/3
5882 reflections(Δ/σ)max = 0.001
279 parametersΔρmax = 0.72 e Å−3
0 restraintsΔρmin = −0.49 e Å−3
Crystal data top
C12H22NSi+·Cl−V = 3006.01 (14) Å3
Mr = 243.85Z = 8
Monoclinic, P21/cCu Kα radiation
a = 12.3716 (4) ŵ = 2.79 mm−1
b = 32.6920 (8) ÅT = 295 K
c = 7.44256 (18) Å0.47 × 0.10 × 0.06 mm
β = 93.006 (2)°
Data collection top
Oxford Diffraction Xcalibur Ruby Gemini
diffractometer		5882 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)		3078 reflections with I > 2σ(I)
Tmin = 0.370, Tmax = 1.000Rint = 0.049
11195 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0760 restraints
wR(F2) = 0.276H-atom parameters constrained
S = 1.14Δρmax = 0.72 e Å−3
5882 reflectionsΔρmin = −0.49 e Å−3
279 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
xyzUiso*/Ueq
Cl10.51262 (14)0.70004 (5)0.46785 (17)0.0747 (4)
Cl20.24050 (12)0.70213 (4)−0.04653 (17)0.0658 (4)
Si1A0.87067 (14)0.68876 (5)0.88371 (19)0.0642 (4)
N1A0.4863 (4)0.70536 (13)0.8840 (5)0.0643 (11)
H1AA0.41500.70500.89430.096*
H1AB0.50080.70410.76820.096*
H1AC0.51350.72840.93140.096*
C1A0.6903 (5)0.62195 (16)1.0207 (6)0.0592 (13)
C2A0.7098 (6)0.58664 (18)0.9246 (8)0.0757 (17)
H2AA0.69820.58640.80010.091*
C3A0.7464 (7)0.5518 (2)1.0127 (10)0.099 (2)
H3AA0.75780.52820.94670.118*
C4A0.7661 (7)0.5512 (2)1.1946 (10)0.103 (2)
H4AA0.79310.52781.25180.123*
C5A0.7459 (6)0.5855 (2)1.2916 (8)0.089 (2)
H5AA0.75830.58531.41590.107*
C6A0.7070 (5)0.62050 (18)1.2066 (7)0.0709 (15)
H6AA0.69180.64341.27490.085*
C7A0.5364 (5)0.66953 (18)0.9814 (7)0.0670 (15)
H7AA0.49160.64560.95760.080*
H7AB0.53810.67481.10980.080*
C8A0.6509 (4)0.66056 (15)0.9266 (6)0.0553 (12)
H8AA0.64630.65470.79720.066*
C9A0.7297 (4)0.69618 (16)0.9563 (7)0.0582 (12)
H9AA0.73380.70271.08370.070*
H9AB0.69920.71980.89340.070*
C10A0.9367 (6)0.73979 (18)0.8718 (7)0.0756 (16)
H10A0.95430.74960.99140.113*
H10B0.88820.75870.81030.113*
H10C1.00170.73740.80760.113*
C11A0.8624 (6)0.6646 (2)0.6552 (9)0.092 (2)
H11A0.81520.68050.57600.138*
H11B0.83460.63730.66380.138*
H11C0.93330.66370.60870.138*
C12A0.9525 (6)0.6562 (2)1.0466 (9)0.093 (2)
H12A0.94670.66671.16620.140*
H12B1.02700.65661.01620.140*
H12C0.92590.62861.04090.140*
Si1B0.36327 (18)0.56463 (5)0.3612 (3)0.0814 (5)
N1B0.2550 (4)0.70271 (12)0.3793 (6)0.0649 (12)
H1BA0.23790.72810.41030.097*
H1BB0.24640.70000.26040.097*
H1BC0.32360.69760.41420.097*
C1B0.1599 (6)0.60320 (17)0.5886 (8)0.0731 (16)
C2B0.0698 (7)0.5861 (2)0.4979 (11)0.097 (2)
H2BA0.05300.59280.37830.116*
C3B0.0038 (7)0.5584 (2)0.5886 (14)0.113 (3)
H3BA−0.05590.54660.52760.136*
C4B0.0263 (9)0.5491 (3)0.7602 (14)0.115 (3)
H4BA−0.01730.53060.81810.137*
C5B0.1124 (10)0.5663 (3)0.8517 (11)0.118 (3)
H5BA0.12650.55990.97240.142*
C6B0.1802 (7)0.5935 (2)0.7679 (9)0.092 (2)
H6BA0.23880.60520.83230.110*
C7B0.1835 (4)0.67343 (15)0.4673 (7)0.0575 (12)
H7BA0.11680.67030.39400.069*
H7BB0.16520.68430.58310.069*
C8B0.2369 (6)0.63141 (17)0.4947 (7)0.0717 (16)
H8BA0.29880.63570.58040.086*
C9B0.2827 (6)0.61330 (18)0.3298 (8)0.0767 (17)
H9BA0.32880.63370.27780.092*
H9BB0.22320.60800.24280.092*
C10B0.4703 (9)0.5713 (3)0.5428 (13)0.140 (4)
H10D0.52530.55100.53080.210*
H10E0.43920.56850.65760.210*
H10F0.50170.59810.53390.210*
C11B0.4268 (8)0.5546 (2)0.1443 (11)0.115 (3)
H11D0.46940.53000.15460.173*
H11E0.47250.57710.11620.173*
H11F0.37140.55130.05030.173*
C12B0.2769 (8)0.52048 (19)0.4136 (12)0.120 (3)
H12D0.31900.49580.41230.181*
H12E0.21770.51860.32520.181*
H12F0.24910.52410.53060.181*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0932 (11)0.0737 (9)0.0567 (7)0.0071 (8)−0.0001 (6)−0.0029 (6)
Cl20.0764 (9)0.0589 (7)0.0617 (7)−0.0045 (7)−0.0010 (6)0.0030 (5)
Si1A0.0727 (10)0.0614 (9)0.0584 (8)−0.0013 (8)0.0027 (7)−0.0008 (6)
N1A0.069 (3)0.068 (3)0.056 (2)0.006 (2)0.000 (2)−0.001 (2)
C1A0.071 (3)0.058 (3)0.050 (2)−0.004 (3)0.003 (2)0.003 (2)
C2A0.105 (5)0.058 (3)0.065 (3)−0.002 (3)0.006 (3)−0.006 (3)
C3A0.135 (7)0.055 (4)0.107 (5)0.009 (4)0.018 (5)−0.006 (3)
C4A0.140 (8)0.072 (4)0.097 (5)0.015 (5)0.008 (5)0.026 (4)
C5A0.108 (6)0.092 (5)0.067 (3)0.021 (4)−0.003 (3)0.021 (3)
C6A0.085 (4)0.067 (3)0.060 (3)0.009 (3)−0.004 (3)0.002 (3)
C7A0.078 (4)0.072 (4)0.051 (2)0.009 (3)0.002 (2)0.007 (2)
C8A0.060 (3)0.060 (3)0.046 (2)0.007 (2)0.001 (2)−0.002 (2)
C9A0.057 (3)0.059 (3)0.058 (3)0.002 (2)−0.004 (2)0.000 (2)
C10A0.092 (5)0.071 (4)0.064 (3)−0.010 (3)0.010 (3)0.001 (3)
C11A0.102 (5)0.092 (5)0.086 (4)−0.011 (4)0.033 (4)−0.028 (4)
C12A0.095 (5)0.077 (4)0.105 (5)0.007 (4)−0.017 (4)0.018 (4)
Si1B0.1019 (14)0.0555 (9)0.0882 (11)0.0095 (10)0.0187 (10)0.0047 (8)
N1B0.086 (3)0.048 (2)0.060 (2)0.001 (2)−0.010 (2)0.0017 (18)
C1B0.090 (5)0.048 (3)0.082 (4)0.003 (3)0.006 (3)−0.001 (3)
C2B0.101 (6)0.081 (5)0.108 (5)0.017 (4)0.003 (4)0.017 (4)
C3B0.097 (6)0.079 (5)0.162 (8)0.000 (5)−0.003 (6)0.013 (5)
C4B0.128 (8)0.080 (5)0.140 (8)−0.004 (5)0.043 (6)0.017 (5)
C5B0.180 (10)0.089 (6)0.091 (5)−0.012 (6)0.048 (6)0.005 (4)
C6B0.128 (6)0.073 (4)0.076 (4)−0.012 (4)0.018 (4)−0.002 (3)
C7B0.061 (3)0.049 (3)0.062 (3)−0.005 (2)−0.004 (2)−0.001 (2)
C8B0.095 (5)0.053 (3)0.067 (3)0.002 (3)0.006 (3)0.006 (2)
C9B0.096 (5)0.060 (3)0.074 (3)0.000 (3)0.005 (3)0.005 (3)
C10B0.148 (9)0.140 (9)0.128 (7)0.027 (7)−0.026 (7)−0.006 (6)
C11B0.154 (8)0.082 (5)0.114 (6)−0.010 (5)0.039 (6)−0.005 (4)
C12B0.172 (9)0.048 (4)0.148 (7)0.012 (5)0.070 (6)0.012 (4)
Geometric parameters (Å, º) top
Si1A—C10A1.862 (6)Si1B—C12B1.850 (8)
Si1A—C9A1.868 (6)Si1B—C10B1.855 (9)
Si1A—C12A1.870 (6)Si1B—C11B1.861 (8)
Si1A—C11A1.872 (6)Si1B—C9B1.886 (6)
N1A—C7A1.495 (6)N1B—C7B1.479 (7)
N1A—H1AA0.8900N1B—H1BA0.8900
N1A—H1AB0.8900N1B—H1BB0.8900
N1A—H1AC0.8900N1B—H1BC0.8900
C1A—C2A1.386 (7)C1B—C6B1.381 (9)
C1A—C6A1.389 (7)C1B—C2B1.391 (10)
C1A—C8A1.512 (7)C1B—C8B1.522 (8)
C2A—C3A1.380 (9)C2B—C3B1.414 (11)
C2A—H2AA0.9300C2B—H2BA0.9300
C3A—C4A1.363 (10)C3B—C4B1.328 (12)
C3A—H3AA0.9300C3B—H3BA0.9300
C4A—C5A1.364 (10)C4B—C5B1.357 (13)
C4A—H4AA0.9300C4B—H4BA0.9300
C5A—C6A1.381 (8)C5B—C6B1.393 (11)
C5A—H5AA0.9300C5B—H5BA0.9300
C6A—H6AA0.9300C6B—H6BA0.9300
C7A—C8A1.523 (8)C7B—C8B1.534 (7)
C7A—H7AA0.9700C7B—H7BA0.9700
C7A—H7AB0.9700C7B—H7BB0.9700
C8A—C9A1.527 (7)C8B—C9B1.500 (8)
C8A—H8AA0.9800C8B—H8BA0.9800
C9A—H9AA0.9700C9B—H9BA0.9700
C9A—H9AB0.9700C9B—H9BB0.9700
C10A—H10A0.9600C10B—H10D0.9600
C10A—H10B0.9600C10B—H10E0.9600
C10A—H10C0.9600C10B—H10F0.9600
C11A—H11A0.9600C11B—H11D0.9600
C11A—H11B0.9600C11B—H11E0.9600
C11A—H11C0.9600C11B—H11F0.9600
C12A—H12A0.9600C12B—H12D0.9600
C12A—H12B0.9600C12B—H12E0.9600
C12A—H12C0.9600C12B—H12F0.9600
C10A—Si1A—C9A108.4 (3)C12B—Si1B—C10B109.7 (5)
C10A—Si1A—C12A108.5 (3)C12B—Si1B—C11B108.7 (4)
C9A—Si1A—C12A111.6 (3)C10B—Si1B—C11B109.6 (5)
C10A—Si1A—C11A109.7 (3)C12B—Si1B—C9B112.1 (4)
C9A—Si1A—C11A108.1 (3)C10B—Si1B—C9B110.1 (4)
C12A—Si1A—C11A110.5 (4)C11B—Si1B—C9B106.7 (3)
C7A—N1A—H1AA109.5C7B—N1B—H1BA109.5
C7A—N1A—H1AB109.5C7B—N1B—H1BB109.5
H1AA—N1A—H1AB109.5H1BA—N1B—H1BB109.5
C7A—N1A—H1AC109.5C7B—N1B—H1BC109.5
H1AA—N1A—H1AC109.5H1BA—N1B—H1BC109.5
H1AB—N1A—H1AC109.5H1BB—N1B—H1BC109.5
C2A—C1A—C6A117.7 (5)C6B—C1B—C2B118.5 (7)
C2A—C1A—C8A121.1 (4)C6B—C1B—C8B119.7 (6)
C6A—C1A—C8A121.2 (5)C2B—C1B—C8B121.8 (6)
C3A—C2A—C1A120.3 (6)C1B—C2B—C3B119.6 (8)
C3A—C2A—H2AA119.8C1B—C2B—H2BA120.2
C1A—C2A—H2AA119.8C3B—C2B—H2BA120.2
C4A—C3A—C2A121.3 (6)C4B—C3B—C2B120.6 (9)
C4A—C3A—H3AA119.3C4B—C3B—H3BA119.7
C2A—C3A—H3AA119.3C2B—C3B—H3BA119.7
C3A—C4A—C5A119.1 (7)C3B—C4B—C5B120.4 (9)
C3A—C4A—H4AA120.4C3B—C4B—H4BA119.8
C5A—C4A—H4AA120.4C5B—C4B—H4BA119.8
C4A—C5A—C6A120.5 (6)C4B—C5B—C6B121.1 (8)
C4A—C5A—H5AA119.8C4B—C5B—H5BA119.5
C6A—C5A—H5AA119.8C6B—C5B—H5BA119.5
C5A—C6A—C1A121.0 (6)C1B—C6B—C5B119.7 (8)
C5A—C6A—H6AA119.5C1B—C6B—H6BA120.1
C1A—C6A—H6AA119.5C5B—C6B—H6BA120.1
N1A—C7A—C8A112.8 (4)N1B—C7B—C8B112.0 (5)
N1A—C7A—H7AA109.0N1B—C7B—H7BA109.2
C8A—C7A—H7AA109.0C8B—C7B—H7BA109.2
N1A—C7A—H7AB109.0N1B—C7B—H7BB109.2
C8A—C7A—H7AB109.0C8B—C7B—H7BB109.2
H7AA—C7A—H7AB107.8H7BA—C7B—H7BB107.9
C1A—C8A—C7A108.5 (4)C9B—C8B—C1B114.1 (5)
C1A—C8A—C9A112.4 (4)C9B—C8B—C7B115.0 (5)
C7A—C8A—C9A114.2 (4)C1B—C8B—C7B109.1 (5)
C1A—C8A—H8AA107.1C9B—C8B—H8BA105.9
C7A—C8A—H8AA107.1C1B—C8B—H8BA105.9
C9A—C8A—H8AA107.1C7B—C8B—H8BA105.9
C8A—C9A—Si1A117.2 (4)C8B—C9B—Si1B116.8 (4)
C8A—C9A—H9AA108.0C8B—C9B—H9BA108.1
Si1A—C9A—H9AA108.0Si1B—C9B—H9BA108.1
C8A—C9A—H9AB108.0C8B—C9B—H9BB108.1
Si1A—C9A—H9AB108.0Si1B—C9B—H9BB108.1
H9AA—C9A—H9AB107.2H9BA—C9B—H9BB107.3
Si1A—C10A—H10A109.5Si1B—C10B—H10D109.5
Si1A—C10A—H10B109.5Si1B—C10B—H10E109.5
H10A—C10A—H10B109.5H10D—C10B—H10E109.5
Si1A—C10A—H10C109.5Si1B—C10B—H10F109.5
H10A—C10A—H10C109.5H10D—C10B—H10F109.5
H10B—C10A—H10C109.5H10E—C10B—H10F109.5
Si1A—C11A—H11A109.5Si1B—C11B—H11D109.5
Si1A—C11A—H11B109.5Si1B—C11B—H11E109.5
H11A—C11A—H11B109.5H11D—C11B—H11E109.5
Si1A—C11A—H11C109.5Si1B—C11B—H11F109.5
H11A—C11A—H11C109.5H11D—C11B—H11F109.5
H11B—C11A—H11C109.5H11E—C11B—H11F109.5
Si1A—C12A—H12A109.5Si1B—C12B—H12D109.5
Si1A—C12A—H12B109.5Si1B—C12B—H12E109.5
H12A—C12A—H12B109.5H12D—C12B—H12E109.5
Si1A—C12A—H12C109.5Si1B—C12B—H12F109.5
H12A—C12A—H12C109.5H12D—C12B—H12F109.5
H12B—C12A—H12C109.5H12E—C12B—H12F109.5
C6A—C1A—C2A—C3A−1.1 (10)C6B—C1B—C2B—C3B−2.1 (11)
C8A—C1A—C2A—C3A179.6 (6)C8B—C1B—C2B—C3B176.7 (7)
C1A—C2A—C3A—C4A−1.2 (12)C1B—C2B—C3B—C4B1.0 (13)
C2A—C3A—C4A—C5A2.2 (14)C2B—C3B—C4B—C5B0.6 (15)
C3A—C4A—C5A—C6A−0.7 (13)C3B—C4B—C5B—C6B−1.1 (15)
C4A—C5A—C6A—C1A−1.6 (12)C2B—C1B—C6B—C5B1.7 (11)
C2A—C1A—C6A—C5A2.5 (10)C8B—C1B—C6B—C5B−177.2 (7)
C8A—C1A—C6A—C5A−178.2 (6)C4B—C5B—C6B—C1B−0.1 (13)
C2A—C1A—C8A—C7A113.5 (6)C6B—C1B—C8B—C9B123.7 (7)
C6A—C1A—C8A—C7A−65.8 (7)C2B—C1B—C8B—C9B−55.1 (9)
C2A—C1A—C8A—C9A−119.2 (6)C6B—C1B—C8B—C7B−106.0 (7)
C6A—C1A—C8A—C9A61.6 (7)C2B—C1B—C8B—C7B75.2 (7)
N1A—C7A—C8A—C1A−175.4 (4)N1B—C7B—C8B—C9B−51.3 (7)
N1A—C7A—C8A—C9A58.3 (6)N1B—C7B—C8B—C1B179.0 (4)
C1A—C8A—C9A—Si1A58.3 (5)C1B—C8B—C9B—Si1B−59.5 (7)
C7A—C8A—C9A—Si1A−177.4 (3)C7B—C8B—C9B—Si1B173.2 (4)
C10A—Si1A—C9A—C8A163.8 (4)C12B—Si1B—C9B—C8B70.1 (6)
C12A—Si1A—C9A—C8A−76.8 (4)C10B—Si1B—C9B—C8B−52.3 (7)
C11A—Si1A—C9A—C8A44.9 (5)C11B—Si1B—C9B—C8B−171.1 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1AA···Cl2i0.892.233.114 (5)173
N1A—H1AB···Cl10.892.253.136 (4)172
N1A—H1AC···Cl1ii0.892.363.168 (5)152
N1B—H1BA···Cl2ii0.892.303.166 (4)163
N1B—H1BB···Cl20.892.283.165 (4)171
N1B—H1BC···Cl10.892.353.222 (5)165
Symmetry codes: (i) x, y, z+1; (ii) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC12H22NSi+·Cl−
Mr243.85
Crystal system, space groupMonoclinic, P21/c
Temperature (K)295
a, b, c (Å)12.3716 (4), 32.6920 (8), 7.44256 (18)
β (°) 93.006 (2)
V (Å3)3006.01 (14)
Z8
Radiation typeCu Kα
µ (mm−1)2.79
Crystal size (mm)0.47 × 0.10 × 0.06
Data collection
DiffractometerOxford Diffraction Xcalibur Ruby Gemini
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
Tmin, Tmax0.370, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		11195, 5882, 3078
Rint0.049
(sin θ/λ)max (Å−1)0.629
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.076, 0.276, 1.14
No. of reflections5882
No. of parameters279
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.72, −0.49

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1AA···Cl2i0.892.233.114 (5)173.4
N1A—H1AB···Cl10.892.253.136 (4)172.1
N1A—H1AC···Cl1ii0.892.363.168 (5)152.0
N1B—H1BA···Cl2ii0.892.303.166 (4)163.4
N1B—H1BB···Cl20.892.283.165 (4)171.0
N1B—H1BC···Cl10.892.353.222 (5)165.3
Symmetry codes: (i) x, y, z+1; (ii) x, −y+3/2, z+1/2.
 

Acknowledgements

RJB wishes to acknowledge the NSF–MRI program (grant CHE-0619278) for funds to purchase the diffractometer. YMH acknowledges partial support from NSF-Rise award # HRD 0627276.

References

First citationAllen, F. H. (2002). Acta Cryst. B58, 380–388.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationBlasucci, V., Hart, R., Mestre, V. L., Hahne, D. J., Burlager, M., Huttenhower, H., Thio, B. J. R., Pollet, P., Liotta, C. L. & Eckert, C. A. (2010). Fuel, 89, 1315–1319.  Web of Science CrossRef CAS Google Scholar
 First citationFrankel, M., Broze, M., Gertner, D., Rotman, A., Shenhar, A. & Zilkha, A. (1968). J. Med. Chem. 11, 857–860.  CrossRef CAS PubMed Web of Science Google Scholar
 First citationLi, J.-R., Lusker, K. L., Yu, J.-J. & Garno, J. C. (2009). ACS Nano, 3, 2023–2035.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationLorenz, M., Linn, M. L. V. & Cook, J. M. (2010). Curr. Org. Synth. 7, 189–223.  CrossRef CAS Google Scholar
 First citationOxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 67| Part 10| October 2011| Page o2553
https://doi.org/10.1107/S1600536811035410
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