2-Phenyl-3-(trimethyl-sil-yl)propan-1-aminium chloride.

The title compound, C(12)H(22)NSi(+)·Cl(-), contains two formula units in the asymmetric unit and is a hydro-chloride salt in which the amine N atom is protonated and the NH(3) (+) 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 ▶). For applications of β-phenyl­ethyl amine in alkaloid synthesis via the 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

Crystal data

C12H22NSi+·Cl−

M = 243.85

Monoclinic,

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 ▶) T min = 0.370, T max = 1.000

11195 measured reflections

5882 independent reflections

3078 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.076

wR(F 2) = 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

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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/S1600536811035410/hg5087sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035410/hg5087Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811035410/hg5087Isup3.cml

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

C12H22NSi+·Cl−	F(000) = 1056
Mr = 243.85	Dx = 1.078 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 3131 reflections
a = 12.3716 (4) Å	θ = 4.5–75.7°
b = 32.6920 (8) Å	µ = 2.79 mm−1
c = 7.44256 (18) Å	T = 295 K
β = 93.006 (2)°	Needle, colorless
V = 3006.01 (14) Å3	0.47 × 0.10 × 0.06 mm
Z = 8

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	5882 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3078 reflections with I > 2σ(I)
graphite	Rint = 0.049
Detector resolution: 10.5081 pixels mm-1	θmax = 76.0°, θmin = 4.5°
ω scans	h = −15→15
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −40→38
Tmin = 0.370, Tmax = 1.000	l = −9→8
11195 measured reflections

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)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.276	H-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 parameters	Δρmax = 0.72 e Å−3
0 restraints	Δρmin = −0.49 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
Cl1	0.51262 (14)	0.70004 (5)	0.46785 (17)	0.0747 (4)
Cl2	0.24050 (12)	0.70213 (4)	−0.04653 (17)	0.0658 (4)
Si1A	0.87067 (14)	0.68876 (5)	0.88371 (19)	0.0642 (4)
N1A	0.4863 (4)	0.70536 (13)	0.8840 (5)	0.0643 (11)
H1AA	0.4150	0.7050	0.8943	0.096*
H1AB	0.5008	0.7041	0.7682	0.096*
H1AC	0.5135	0.7284	0.9314	0.096*
C1A	0.6903 (5)	0.62195 (16)	1.0207 (6)	0.0592 (13)
C2A	0.7098 (6)	0.58664 (18)	0.9246 (8)	0.0757 (17)
H2AA	0.6982	0.5864	0.8001	0.091*
C3A	0.7464 (7)	0.5518 (2)	1.0127 (10)	0.099 (2)
H3AA	0.7578	0.5282	0.9467	0.118*
C4A	0.7661 (7)	0.5512 (2)	1.1946 (10)	0.103 (2)
H4AA	0.7931	0.5278	1.2518	0.123*
C5A	0.7459 (6)	0.5855 (2)	1.2916 (8)	0.089 (2)
H5AA	0.7583	0.5853	1.4159	0.107*
C6A	0.7070 (5)	0.62050 (18)	1.2066 (7)	0.0709 (15)
H6AA	0.6918	0.6434	1.2749	0.085*
C7A	0.5364 (5)	0.66953 (18)	0.9814 (7)	0.0670 (15)
H7AA	0.4916	0.6456	0.9576	0.080*
H7AB	0.5381	0.6748	1.1098	0.080*
C8A	0.6509 (4)	0.66056 (15)	0.9266 (6)	0.0553 (12)
H8AA	0.6463	0.6547	0.7972	0.066*
C9A	0.7297 (4)	0.69618 (16)	0.9563 (7)	0.0582 (12)
H9AA	0.7338	0.7027	1.0837	0.070*
H9AB	0.6992	0.7198	0.8934	0.070*
C10A	0.9367 (6)	0.73979 (18)	0.8718 (7)	0.0756 (16)
H10A	0.9543	0.7496	0.9914	0.113*
H10B	0.8882	0.7587	0.8103	0.113*
H10C	1.0017	0.7374	0.8076	0.113*
C11A	0.8624 (6)	0.6646 (2)	0.6552 (9)	0.092 (2)
H11A	0.8152	0.6805	0.5760	0.138*
H11B	0.8346	0.6373	0.6638	0.138*
H11C	0.9333	0.6637	0.6087	0.138*
C12A	0.9525 (6)	0.6562 (2)	1.0466 (9)	0.093 (2)
H12A	0.9467	0.6667	1.1662	0.140*
H12B	1.0270	0.6566	1.0162	0.140*
H12C	0.9259	0.6286	1.0409	0.140*
Si1B	0.36327 (18)	0.56463 (5)	0.3612 (3)	0.0814 (5)
N1B	0.2550 (4)	0.70271 (12)	0.3793 (6)	0.0649 (12)
H1BA	0.2379	0.7281	0.4103	0.097*
H1BB	0.2464	0.7000	0.2604	0.097*
H1BC	0.3236	0.6976	0.4142	0.097*
C1B	0.1599 (6)	0.60320 (17)	0.5886 (8)	0.0731 (16)
C2B	0.0698 (7)	0.5861 (2)	0.4979 (11)	0.097 (2)
H2BA	0.0530	0.5928	0.3783	0.116*
C3B	0.0038 (7)	0.5584 (2)	0.5886 (14)	0.113 (3)
H3BA	−0.0559	0.5466	0.5276	0.136*
C4B	0.0263 (9)	0.5491 (3)	0.7602 (14)	0.115 (3)
H4BA	−0.0173	0.5306	0.8181	0.137*
C5B	0.1124 (10)	0.5663 (3)	0.8517 (11)	0.118 (3)
H5BA	0.1265	0.5599	0.9724	0.142*
C6B	0.1802 (7)	0.5935 (2)	0.7679 (9)	0.092 (2)
H6BA	0.2388	0.6052	0.8323	0.110*
C7B	0.1835 (4)	0.67343 (15)	0.4673 (7)	0.0575 (12)
H7BA	0.1168	0.6703	0.3940	0.069*
H7BB	0.1652	0.6843	0.5831	0.069*
C8B	0.2369 (6)	0.63141 (17)	0.4947 (7)	0.0717 (16)
H8BA	0.2988	0.6357	0.5804	0.086*
C9B	0.2827 (6)	0.61330 (18)	0.3298 (8)	0.0767 (17)
H9BA	0.3288	0.6337	0.2778	0.092*
H9BB	0.2232	0.6080	0.2428	0.092*
C10B	0.4703 (9)	0.5713 (3)	0.5428 (13)	0.140 (4)
H10D	0.5253	0.5510	0.5308	0.210*
H10E	0.4392	0.5685	0.6576	0.210*
H10F	0.5017	0.5981	0.5339	0.210*
C11B	0.4268 (8)	0.5546 (2)	0.1443 (11)	0.115 (3)
H11D	0.4694	0.5300	0.1546	0.173*
H11E	0.4725	0.5771	0.1162	0.173*
H11F	0.3714	0.5513	0.0503	0.173*
C12B	0.2769 (8)	0.52048 (19)	0.4136 (12)	0.120 (3)
H12D	0.3190	0.4958	0.4123	0.181*
H12E	0.2177	0.5186	0.3252	0.181*
H12F	0.2491	0.5241	0.5306	0.181*

	U11	U22	U33	U12	U13	U23
Cl1	0.0932 (11)	0.0737 (9)	0.0567 (7)	0.0071 (8)	−0.0001 (6)	−0.0029 (6)
Cl2	0.0764 (9)	0.0589 (7)	0.0617 (7)	−0.0045 (7)	−0.0010 (6)	0.0030 (5)
Si1A	0.0727 (10)	0.0614 (9)	0.0584 (8)	−0.0013 (8)	0.0027 (7)	−0.0008 (6)
N1A	0.069 (3)	0.068 (3)	0.056 (2)	0.006 (2)	0.000 (2)	−0.001 (2)
C1A	0.071 (3)	0.058 (3)	0.050 (2)	−0.004 (3)	0.003 (2)	0.003 (2)
C2A	0.105 (5)	0.058 (3)	0.065 (3)	−0.002 (3)	0.006 (3)	−0.006 (3)
C3A	0.135 (7)	0.055 (4)	0.107 (5)	0.009 (4)	0.018 (5)	−0.006 (3)
C4A	0.140 (8)	0.072 (4)	0.097 (5)	0.015 (5)	0.008 (5)	0.026 (4)
C5A	0.108 (6)	0.092 (5)	0.067 (3)	0.021 (4)	−0.003 (3)	0.021 (3)
C6A	0.085 (4)	0.067 (3)	0.060 (3)	0.009 (3)	−0.004 (3)	0.002 (3)
C7A	0.078 (4)	0.072 (4)	0.051 (2)	0.009 (3)	0.002 (2)	0.007 (2)
C8A	0.060 (3)	0.060 (3)	0.046 (2)	0.007 (2)	0.001 (2)	−0.002 (2)
C9A	0.057 (3)	0.059 (3)	0.058 (3)	0.002 (2)	−0.004 (2)	0.000 (2)
C10A	0.092 (5)	0.071 (4)	0.064 (3)	−0.010 (3)	0.010 (3)	0.001 (3)
C11A	0.102 (5)	0.092 (5)	0.086 (4)	−0.011 (4)	0.033 (4)	−0.028 (4)
C12A	0.095 (5)	0.077 (4)	0.105 (5)	0.007 (4)	−0.017 (4)	0.018 (4)
Si1B	0.1019 (14)	0.0555 (9)	0.0882 (11)	0.0095 (10)	0.0187 (10)	0.0047 (8)
N1B	0.086 (3)	0.048 (2)	0.060 (2)	0.001 (2)	−0.010 (2)	0.0017 (18)
C1B	0.090 (5)	0.048 (3)	0.082 (4)	0.003 (3)	0.006 (3)	−0.001 (3)
C2B	0.101 (6)	0.081 (5)	0.108 (5)	0.017 (4)	0.003 (4)	0.017 (4)
C3B	0.097 (6)	0.079 (5)	0.162 (8)	0.000 (5)	−0.003 (6)	0.013 (5)
C4B	0.128 (8)	0.080 (5)	0.140 (8)	−0.004 (5)	0.043 (6)	0.017 (5)
C5B	0.180 (10)	0.089 (6)	0.091 (5)	−0.012 (6)	0.048 (6)	0.005 (4)
C6B	0.128 (6)	0.073 (4)	0.076 (4)	−0.012 (4)	0.018 (4)	−0.002 (3)
C7B	0.061 (3)	0.049 (3)	0.062 (3)	−0.005 (2)	−0.004 (2)	−0.001 (2)
C8B	0.095 (5)	0.053 (3)	0.067 (3)	0.002 (3)	0.006 (3)	0.006 (2)
C9B	0.096 (5)	0.060 (3)	0.074 (3)	0.000 (3)	0.005 (3)	0.005 (3)
C10B	0.148 (9)	0.140 (9)	0.128 (7)	0.027 (7)	−0.026 (7)	−0.006 (6)
C11B	0.154 (8)	0.082 (5)	0.114 (6)	−0.010 (5)	0.039 (6)	−0.005 (4)
C12B	0.172 (9)	0.048 (4)	0.148 (7)	0.012 (5)	0.070 (6)	0.012 (4)

Si1A—C10A	1.862 (6)	Si1B—C12B	1.850 (8)
Si1A—C9A	1.868 (6)	Si1B—C10B	1.855 (9)
Si1A—C12A	1.870 (6)	Si1B—C11B	1.861 (8)
Si1A—C11A	1.872 (6)	Si1B—C9B	1.886 (6)
N1A—C7A	1.495 (6)	N1B—C7B	1.479 (7)
N1A—H1AA	0.8900	N1B—H1BA	0.8900
N1A—H1AB	0.8900	N1B—H1BB	0.8900
N1A—H1AC	0.8900	N1B—H1BC	0.8900
C1A—C2A	1.386 (7)	C1B—C6B	1.381 (9)
C1A—C6A	1.389 (7)	C1B—C2B	1.391 (10)
C1A—C8A	1.512 (7)	C1B—C8B	1.522 (8)
C2A—C3A	1.380 (9)	C2B—C3B	1.414 (11)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.363 (10)	C3B—C4B	1.328 (12)
C3A—H3AA	0.9300	C3B—H3BA	0.9300
C4A—C5A	1.364 (10)	C4B—C5B	1.357 (13)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.381 (8)	C5B—C6B	1.393 (11)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C6A—H6AA	0.9300	C6B—H6BA	0.9300
C7A—C8A	1.523 (8)	C7B—C8B	1.534 (7)
C7A—H7AA	0.9700	C7B—H7BA	0.9700
C7A—H7AB	0.9700	C7B—H7BB	0.9700
C8A—C9A	1.527 (7)	C8B—C9B	1.500 (8)
C8A—H8AA	0.9800	C8B—H8BA	0.9800
C9A—H9AA	0.9700	C9B—H9BA	0.9700
C9A—H9AB	0.9700	C9B—H9BB	0.9700
C10A—H10A	0.9600	C10B—H10D	0.9600
C10A—H10B	0.9600	C10B—H10E	0.9600
C10A—H10C	0.9600	C10B—H10F	0.9600
C11A—H11A	0.9600	C11B—H11D	0.9600
C11A—H11B	0.9600	C11B—H11E	0.9600
C11A—H11C	0.9600	C11B—H11F	0.9600
C12A—H12A	0.9600	C12B—H12D	0.9600
C12A—H12B	0.9600	C12B—H12E	0.9600
C12A—H12C	0.9600	C12B—H12F	0.9600
C10A—Si1A—C9A	108.4 (3)	C12B—Si1B—C10B	109.7 (5)
C10A—Si1A—C12A	108.5 (3)	C12B—Si1B—C11B	108.7 (4)
C9A—Si1A—C12A	111.6 (3)	C10B—Si1B—C11B	109.6 (5)
C10A—Si1A—C11A	109.7 (3)	C12B—Si1B—C9B	112.1 (4)
C9A—Si1A—C11A	108.1 (3)	C10B—Si1B—C9B	110.1 (4)
C12A—Si1A—C11A	110.5 (4)	C11B—Si1B—C9B	106.7 (3)
C7A—N1A—H1AA	109.5	C7B—N1B—H1BA	109.5
C7A—N1A—H1AB	109.5	C7B—N1B—H1BB	109.5
H1AA—N1A—H1AB	109.5	H1BA—N1B—H1BB	109.5
C7A—N1A—H1AC	109.5	C7B—N1B—H1BC	109.5
H1AA—N1A—H1AC	109.5	H1BA—N1B—H1BC	109.5
H1AB—N1A—H1AC	109.5	H1BB—N1B—H1BC	109.5
C2A—C1A—C6A	117.7 (5)	C6B—C1B—C2B	118.5 (7)
C2A—C1A—C8A	121.1 (4)	C6B—C1B—C8B	119.7 (6)
C6A—C1A—C8A	121.2 (5)	C2B—C1B—C8B	121.8 (6)
C3A—C2A—C1A	120.3 (6)	C1B—C2B—C3B	119.6 (8)
C3A—C2A—H2AA	119.8	C1B—C2B—H2BA	120.2
C1A—C2A—H2AA	119.8	C3B—C2B—H2BA	120.2
C4A—C3A—C2A	121.3 (6)	C4B—C3B—C2B	120.6 (9)
C4A—C3A—H3AA	119.3	C4B—C3B—H3BA	119.7
C2A—C3A—H3AA	119.3	C2B—C3B—H3BA	119.7
C3A—C4A—C5A	119.1 (7)	C3B—C4B—C5B	120.4 (9)
C3A—C4A—H4AA	120.4	C3B—C4B—H4BA	119.8
C5A—C4A—H4AA	120.4	C5B—C4B—H4BA	119.8
C4A—C5A—C6A	120.5 (6)	C4B—C5B—C6B	121.1 (8)
C4A—C5A—H5AA	119.8	C4B—C5B—H5BA	119.5
C6A—C5A—H5AA	119.8	C6B—C5B—H5BA	119.5
C5A—C6A—C1A	121.0 (6)	C1B—C6B—C5B	119.7 (8)
C5A—C6A—H6AA	119.5	C1B—C6B—H6BA	120.1
C1A—C6A—H6AA	119.5	C5B—C6B—H6BA	120.1
N1A—C7A—C8A	112.8 (4)	N1B—C7B—C8B	112.0 (5)
N1A—C7A—H7AA	109.0	N1B—C7B—H7BA	109.2
C8A—C7A—H7AA	109.0	C8B—C7B—H7BA	109.2
N1A—C7A—H7AB	109.0	N1B—C7B—H7BB	109.2
C8A—C7A—H7AB	109.0	C8B—C7B—H7BB	109.2
H7AA—C7A—H7AB	107.8	H7BA—C7B—H7BB	107.9
C1A—C8A—C7A	108.5 (4)	C9B—C8B—C1B	114.1 (5)
C1A—C8A—C9A	112.4 (4)	C9B—C8B—C7B	115.0 (5)
C7A—C8A—C9A	114.2 (4)	C1B—C8B—C7B	109.1 (5)
C1A—C8A—H8AA	107.1	C9B—C8B—H8BA	105.9
C7A—C8A—H8AA	107.1	C1B—C8B—H8BA	105.9
C9A—C8A—H8AA	107.1	C7B—C8B—H8BA	105.9
C8A—C9A—Si1A	117.2 (4)	C8B—C9B—Si1B	116.8 (4)
C8A—C9A—H9AA	108.0	C8B—C9B—H9BA	108.1
Si1A—C9A—H9AA	108.0	Si1B—C9B—H9BA	108.1
C8A—C9A—H9AB	108.0	C8B—C9B—H9BB	108.1
Si1A—C9A—H9AB	108.0	Si1B—C9B—H9BB	108.1
H9AA—C9A—H9AB	107.2	H9BA—C9B—H9BB	107.3
Si1A—C10A—H10A	109.5	Si1B—C10B—H10D	109.5
Si1A—C10A—H10B	109.5	Si1B—C10B—H10E	109.5
H10A—C10A—H10B	109.5	H10D—C10B—H10E	109.5
Si1A—C10A—H10C	109.5	Si1B—C10B—H10F	109.5
H10A—C10A—H10C	109.5	H10D—C10B—H10F	109.5
H10B—C10A—H10C	109.5	H10E—C10B—H10F	109.5
Si1A—C11A—H11A	109.5	Si1B—C11B—H11D	109.5
Si1A—C11A—H11B	109.5	Si1B—C11B—H11E	109.5
H11A—C11A—H11B	109.5	H11D—C11B—H11E	109.5
Si1A—C11A—H11C	109.5	Si1B—C11B—H11F	109.5
H11A—C11A—H11C	109.5	H11D—C11B—H11F	109.5
H11B—C11A—H11C	109.5	H11E—C11B—H11F	109.5
Si1A—C12A—H12A	109.5	Si1B—C12B—H12D	109.5
Si1A—C12A—H12B	109.5	Si1B—C12B—H12E	109.5
H12A—C12A—H12B	109.5	H12D—C12B—H12E	109.5
Si1A—C12A—H12C	109.5	Si1B—C12B—H12F	109.5
H12A—C12A—H12C	109.5	H12D—C12B—H12F	109.5
H12B—C12A—H12C	109.5	H12E—C12B—H12F	109.5
C6A—C1A—C2A—C3A	−1.1 (10)	C6B—C1B—C2B—C3B	−2.1 (11)
C8A—C1A—C2A—C3A	179.6 (6)	C8B—C1B—C2B—C3B	176.7 (7)
C1A—C2A—C3A—C4A	−1.2 (12)	C1B—C2B—C3B—C4B	1.0 (13)
C2A—C3A—C4A—C5A	2.2 (14)	C2B—C3B—C4B—C5B	0.6 (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—C5B	1.7 (11)
C2A—C1A—C6A—C5A	2.5 (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—C7A	113.5 (6)	C6B—C1B—C8B—C9B	123.7 (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—C9A	61.6 (7)	C2B—C1B—C8B—C7B	75.2 (7)
N1A—C7A—C8A—C1A	−175.4 (4)	N1B—C7B—C8B—C9B	−51.3 (7)
N1A—C7A—C8A—C9A	58.3 (6)	N1B—C7B—C8B—C1B	179.0 (4)
C1A—C8A—C9A—Si1A	58.3 (5)	C1B—C8B—C9B—Si1B	−59.5 (7)
C7A—C8A—C9A—Si1A	−177.4 (3)	C7B—C8B—C9B—Si1B	173.2 (4)
C10A—Si1A—C9A—C8A	163.8 (4)	C12B—Si1B—C9B—C8B	70.1 (6)
C12A—Si1A—C9A—C8A	−76.8 (4)	C10B—Si1B—C9B—C8B	−52.3 (7)
C11A—Si1A—C9A—C8A	44.9 (5)	C11B—Si1B—C9B—C8B	−171.1 (6)

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.

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) ; (ii) .