2-(4-Hy-droxy-phen-yl)-3-(trimethyl-sil-yl)propanaminium chloride.

In the title crystal structure, C(12)H(22)NOSi(+)·Cl(-), anions and cations are linked via O-H⋯Cl, N-H⋯Cl and N-H⋯O hydrogen bonds to form a two-dimensional network parallel to (101). Within the hydrogen-bonded network, R(4) (2)(22) ring motifs are stacked along [010].

Related literature

For silicon-substituted β-phenyl­ethyl amines and their 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 the uses and applications of 3-amino-propyl­silanes in nanotechnology and self-assembled monolayers, see: Li et al. (2009 ▶). For the uses and applications in reverse ionic liquids in oil extraction, see: Blasucci et al. (2010 ▶). For a related structure, see: Hijji et al. (2011 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C12H22NOSi+·Cl−

M = 259.85

Monoclinic,

a = 14.2611 (4) Å

b = 6.7587 (2) Å

c = 16.0316 (9) Å

β = 91.252 (3)°

V = 1544.86 (11) Å3

Z = 4

Cu Kα radiation

μ = 2.79 mm−1

T = 295 K

0.44 × 0.18 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.713, T max = 1.000

5741 measured reflections

3065 independent reflections

2023 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.244

S = 1.14

3065 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.46 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/S1600536811037639/lh5328sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037639/lh5328Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811037639/lh5328Isup3.cml

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

C12H22NOSi+·Cl−	F(000) = 560
Mr = 259.85	Dx = 1.117 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 1894 reflections
a = 14.2611 (4) Å	θ = 5.5–75.6°
b = 6.7587 (2) Å	µ = 2.79 mm−1
c = 16.0316 (9) Å	T = 295 K
β = 91.252 (3)°	Needle, colorless
V = 1544.86 (11) Å3	0.44 × 0.18 × 0.06 mm
Z = 4

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	3065 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2023 reflections with I > 2σ(I)
graphite	Rint = 0.034
Detector resolution: 10.5081 pixels mm-1	θmax = 75.8°, θmin = 5.5°
ω scans	h = −17→15
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −8→5
Tmin = 0.713, Tmax = 1.000	l = −17→20
5741 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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.244	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.1021P)2 + 1.2793P] where P = (Fo2 + 2Fc2)/3
3065 reflections	(Δ/σ)max = 0.002
146 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.46 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
Cl	0.79604 (9)	−0.16189 (18)	0.66227 (8)	0.0740 (4)
Si	0.60028 (10)	0.1988 (3)	0.36494 (9)	0.0772 (5)
O1	1.0447 (2)	0.4507 (5)	0.3547 (2)	0.0716 (9)
H1	1.0773	0.3522	0.3484	0.107*
N1	0.7889 (3)	0.2955 (6)	0.6591 (2)	0.0607 (9)
H1A	0.7848	0.3526	0.7090	0.091*
H1B	0.8399	0.3391	0.6340	0.091*
H1C	0.7926	0.1649	0.6654	0.091*
C1	0.8001 (3)	0.3071 (6)	0.4778 (2)	0.0532 (9)
C2	0.8626 (3)	0.1619 (7)	0.4569 (3)	0.0631 (11)
H2A	0.8498	0.0312	0.4706	0.076*
C3	0.9446 (3)	0.2058 (7)	0.4155 (3)	0.0672 (12)
H3A	0.9856	0.1049	0.4011	0.081*
C4	0.9650 (3)	0.3994 (7)	0.3960 (3)	0.0566 (10)
C5	0.9045 (3)	0.5478 (7)	0.4181 (3)	0.0611 (10)
H5A	0.9185	0.6789	0.4060	0.073*
C6	0.8227 (3)	0.5012 (7)	0.4584 (3)	0.0627 (11)
H6A	0.7819	0.6023	0.4728	0.075*
C7	0.7046 (3)	0.3453 (7)	0.6075 (3)	0.0654 (11)
H7A	0.6992	0.4880	0.6029	0.078*
H7B	0.6491	0.2965	0.6348	0.078*
C8	0.7093 (3)	0.2553 (7)	0.5201 (3)	0.0636 (11)
H8A	0.7077	0.1111	0.5264	0.076*
C9	0.6207 (4)	0.3158 (8)	0.4699 (3)	0.0745 (13)
H9A	0.6225	0.4580	0.4622	0.089*
H9B	0.5668	0.2868	0.5037	0.089*
C10	0.6136 (6)	−0.0743 (10)	0.3729 (5)	0.119 (2)
H10A	0.6038	−0.1327	0.3188	0.179*
H10B	0.5683	−0.1257	0.4106	0.179*
H10C	0.6756	−0.1055	0.3934	0.179*
C11	0.4808 (4)	0.2622 (16)	0.3295 (6)	0.156 (4)
H11A	0.4686	0.2045	0.2756	0.234*
H11B	0.4748	0.4034	0.3257	0.234*
H11C	0.4367	0.2119	0.3685	0.234*
C12	0.6839 (5)	0.2972 (12)	0.2874 (4)	0.108 (2)
H12A	0.6725	0.2343	0.2344	0.163*
H12B	0.7471	0.2704	0.3061	0.163*
H12C	0.6753	0.4374	0.2816	0.163*

	U11	U22	U33	U12	U13	U23
Cl	0.0907 (9)	0.0624 (7)	0.0700 (7)	0.0036 (6)	0.0276 (6)	−0.0015 (5)
Si	0.0625 (8)	0.0911 (11)	0.0776 (9)	0.0034 (7)	−0.0070 (6)	−0.0219 (8)
O1	0.0607 (18)	0.075 (2)	0.080 (2)	−0.0050 (16)	0.0195 (15)	0.0089 (18)
N1	0.067 (2)	0.062 (2)	0.0531 (18)	−0.0084 (18)	0.0123 (16)	−0.0044 (16)
C1	0.053 (2)	0.061 (2)	0.0455 (19)	−0.0004 (18)	0.0028 (15)	−0.0042 (17)
C2	0.071 (3)	0.053 (2)	0.066 (3)	−0.004 (2)	0.010 (2)	0.001 (2)
C3	0.072 (3)	0.058 (2)	0.072 (3)	0.004 (2)	0.013 (2)	0.001 (2)
C4	0.054 (2)	0.066 (2)	0.050 (2)	−0.0039 (19)	0.0031 (16)	0.0018 (18)
C5	0.073 (3)	0.054 (2)	0.056 (2)	−0.002 (2)	−0.0016 (19)	0.0050 (19)
C6	0.069 (3)	0.060 (2)	0.059 (2)	0.010 (2)	0.0017 (19)	−0.002 (2)
C7	0.073 (3)	0.068 (3)	0.056 (2)	0.001 (2)	0.009 (2)	−0.006 (2)
C8	0.068 (3)	0.066 (3)	0.057 (2)	−0.005 (2)	0.0051 (19)	−0.006 (2)
C9	0.071 (3)	0.082 (3)	0.070 (3)	0.002 (3)	0.001 (2)	−0.012 (3)
C10	0.139 (6)	0.090 (5)	0.130 (6)	−0.005 (5)	0.014 (5)	−0.019 (4)
C11	0.042 (3)	0.243 (11)	0.182 (8)	0.042 (4)	−0.031 (4)	−0.097 (8)
C12	0.127 (6)	0.128 (6)	0.070 (3)	−0.010 (5)	−0.005 (3)	−0.007 (4)

Si—C11	1.835 (6)	C5—H5A	0.9300
Si—C10	1.860 (7)	C6—H6A	0.9300
Si—C12	1.865 (7)	C7—C8	1.532 (6)
Si—C9	1.876 (5)	C7—H7A	0.9700
O1—C4	1.372 (5)	C7—H7B	0.9700
O1—H1	0.8200	C8—C9	1.537 (7)
N1—C7	1.484 (6)	C8—H8A	0.9800
N1—H1A	0.8900	C9—H9A	0.9700
N1—H1B	0.8900	C9—H9B	0.9700
N1—H1C	0.8900	C10—H10A	0.9600
C1—C2	1.373 (6)	C10—H10B	0.9600
C1—C6	1.389 (6)	C10—H10C	0.9600
C1—C8	1.516 (6)	C11—H11A	0.9600
C2—C3	1.388 (6)	C11—H11B	0.9600
C2—H2A	0.9300	C11—H11C	0.9600
C3—C4	1.379 (6)	C12—H12A	0.9600
C3—H3A	0.9300	C12—H12B	0.9600
C4—C5	1.375 (6)	C12—H12C	0.9600
C5—C6	1.381 (6)
C11—Si—C10	110.2 (4)	N1—C7—H7B	109.3
C11—Si—C12	108.3 (4)	C8—C7—H7B	109.3
C10—Si—C12	109.5 (4)	H7A—C7—H7B	107.9
C11—Si—C9	107.7 (3)	C1—C8—C7	111.8 (4)
C10—Si—C9	110.1 (3)	C1—C8—C9	113.9 (4)
C12—Si—C9	111.1 (3)	C7—C8—C9	108.7 (4)
C4—O1—H1	109.5	C1—C8—H8A	107.3
C7—N1—H1A	109.5	C7—C8—H8A	107.3
C7—N1—H1B	109.5	C9—C8—H8A	107.3
H1A—N1—H1B	109.5	C8—C9—Si	117.8 (3)
C7—N1—H1C	109.5	C8—C9—H9A	107.9
H1A—N1—H1C	109.5	Si—C9—H9A	107.9
H1B—N1—H1C	109.5	C8—C9—H9B	107.9
C2—C1—C6	117.7 (4)	Si—C9—H9B	107.9
C2—C1—C8	120.7 (4)	H9A—C9—H9B	107.2
C6—C1—C8	121.6 (4)	Si—C10—H10A	109.5
C1—C2—C3	121.5 (4)	Si—C10—H10B	109.5
C1—C2—H2A	119.2	H10A—C10—H10B	109.5
C3—C2—H2A	119.2	Si—C10—H10C	109.5
C4—C3—C2	119.7 (4)	H10A—C10—H10C	109.5
C4—C3—H3A	120.2	H10B—C10—H10C	109.5
C2—C3—H3A	120.2	Si—C11—H11A	109.5
O1—C4—C5	118.1 (4)	Si—C11—H11B	109.5
O1—C4—C3	122.0 (4)	H11A—C11—H11B	109.5
C5—C4—C3	119.8 (4)	Si—C11—H11C	109.5
C4—C5—C6	119.7 (4)	H11A—C11—H11C	109.5
C4—C5—H5A	120.2	H11B—C11—H11C	109.5
C6—C5—H5A	120.2	Si—C12—H12A	109.5
C5—C6—C1	121.5 (4)	Si—C12—H12B	109.5
C5—C6—H6A	119.2	H12A—C12—H12B	109.5
C1—C6—H6A	119.2	Si—C12—H12C	109.5
N1—C7—C8	111.7 (4)	H12A—C12—H12C	109.5
N1—C7—H7A	109.3	H12B—C12—H12C	109.5
C8—C7—H7A	109.3
C6—C1—C2—C3	−1.7 (7)	C6—C1—C8—C7	−63.8 (5)
C8—C1—C2—C3	177.7 (4)	C2—C1—C8—C9	−119.4 (5)
C1—C2—C3—C4	1.0 (7)	C6—C1—C8—C9	60.0 (6)
C2—C3—C4—O1	−179.6 (4)	N1—C7—C8—C1	−52.4 (5)
C2—C3—C4—C5	0.5 (7)	N1—C7—C8—C9	−179.1 (4)
O1—C4—C5—C6	178.8 (4)	C1—C8—C9—Si	62.4 (5)
C3—C4—C5—C6	−1.3 (7)	C7—C8—C9—Si	−172.2 (4)
C4—C5—C6—C1	0.5 (7)	C11—Si—C9—C8	169.6 (5)
C2—C1—C6—C5	1.0 (7)	C10—Si—C9—C8	49.4 (5)
C8—C1—C6—C5	−178.4 (4)	C12—Si—C9—C8	−72.0 (5)
C2—C1—C8—C7	116.8 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cli	0.82	2.23	3.012 (4)	160.
N1—H1A···Clii	0.89	2.39	3.146 (3)	143.
N1—H1B···O1iii	0.89	2.18	2.941 (5)	143.
N1—H1C···Cl	0.89	2.21	3.093 (4)	172.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯Cli	0.82	2.23	3.012 (4)	160
N1—H1A⋯Clii	0.89	2.39	3.146 (3)	143
N1—H1B⋯O1iii	0.89	2.18	2.941 (5)	143
N1—H1C⋯Cl	0.89	2.21	3.093 (4)	172

Symmetry codes: (i) ; (ii) ; (iii) .