1-Benzyl-3-[(trimethyl­sil­yl)meth­yl]benzimidazolium chloride monohydrate

Akkurt, M.; Çelik, Í.; Küçükbay, H.; Şireci, N.; Büyükgüngör, O.

doi:10.1107/S1600536810024128

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Pages o1770-o1771

doi:10.1107/S1600536810024128

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1-Benzyl-3-[(trimethylsilyl)methyl]benzimidazolium chloride monohydrate

Mehmet Akkurt,^a ^* Ísmail Çelik,^b Hasan Küçükbay,^c Nihat Şireci ^d and Orhan Büyükgüngör ^e

^aDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bDepartment of Physics, Faculty of Arts and Sciences, Cumhuriyet University, 58140 Sivas, Turkey, ^cDepartment of Chemistry, Faculty of Arts and Sciences, Ínönü University, 44280 Malatya, Turkey, ^dDepartment of Chemistry, Faculty of Arts and Sciences, Adıyaman University, 02040 Adıyaman, Turkey, and ^eDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 14 June 2010; accepted 21 June 2010; online 26 June 2010)

The title compound, C₁₈H₂₃N₂Si⁺·Cl⁻·H₂O, was synthesized from 1-[(trimethylsilyl)methyl]benzimidazole and benzyl chloride in dimethylformamide. The benzimidazole ring system is approximately planar, with a maximum deviation of 0.022 (2) Å, and makes an angle of 74.80 (12)° with the phenyl ring. The crystal packing is stabilized by O—H⋯Cl, C—H⋯Cl, C—H⋯O and C—H⋯π interactions between symmetry-related molecules together with π–π stacking interactions between the imidazolium and benzene rings [centroid–centroid distance = 3.5690 (15) Å] and between the benzene rings [centroid–centroid distance = 3.7223 (14) Å].

Related literature

For general background to benzimidazole compounds and for the biological activity of related structures, see: Galal et al. (2009 ); Huang et al. (2006 ); Küçükbay & Durmaz (1997 ); Küçükbay et al. (1995 , 2003 , 2004 , 2010 ); Lukevics et al. (2001 ); Singh & Lown (2000 ); Tavman et al. (2005 ); Turner & Denny (1996 ); Williams et al. (2002 ); Yılmaz & Küçükbay (2009 ); Çetinkaya et al. (1996 ). For similar structures, see: Akkurt et al. (2008 , 2010 ).

Experimental

Crystal data

C₁₈H₂₃N₂Si⁺·Cl⁻·H₂O
M_r = 348.94
Triclinic, $[P \overline 1]$
a = 9.3592 (7) Å
b = 10.9500 (9) Å
c = 11.0522 (8) Å
α = 117.594 (6)°
β = 103.295 (6)°
γ = 92.094 (6)°
V = 963.39 (15) Å³
Z = 2
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 296 K
0.57 × 0.50 × 0.36 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.859, T_max = 0.909
12149 measured reflections
3987 independent reflections
3241 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.135
S = 1.07
3987 reflections
211 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯Cl1	0.86	2.45	3.257 (2)	157
O1—H1B⋯Cl1ⁱ	0.85	2.45	3.250 (3)	158
C7—H7⋯O1	0.93	2.51	3.170 (3)	128
C8—H8A⋯Cl1	0.97	2.81	3.703 (2)	153
C3—H3⋯Cg3ⁱⁱ	0.93	2.69	3.526 (2)	151
Symmetry codes: (i) -x+2, -y+1, -z+2; (ii) x-1, y, z.

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ), ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810024128/dn2582sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810024128/dn2582Isup2.hkl

checkCIF report

Comment top

Although there are different antibacterial and antifungal drugs used in the treatment of bacterial and fungal infections, some of them have undesirable side effects. In addition, some of them become less effective due to the development of resistance to these drugs (Williams et al., 2002). Therefore, many clinically effective antibacterial and antifungal drugs have become less effective due to the development of resistance to these drugs. Since, benzimidazole compounds have been found to have a broad range of pharmacological activity, many research groups as well as our group have been interested in these type of heterocyclic compounds (Singh et al., 2000; Huang et al. 2006; Turner & Denny, 1996; Lukevics et al., 2001; Galal et al. 2009; Çetinkaya et al., 1996; Küçükbay et al., 1995, 1997, 2003, 2004, 2010; Yılmaz & Küçükbay, 2009; Tavman et al., 2005). In recent years, considerable attention has been given to the synthesis of alkylsilyl substituted benzimidazole derivatives because of their properties in cancer therapy. For example, 1-(3-trimethylsilylpropyl)benzimidazole inhibits carcinoma S-180 tumour growth in dose 1 mg.kg^-1 by 62% (on ICR mice) (Lukevics et al., 2001). These properties of silylsubstituted benzimidazole compounds, triggered us to synthesis novel trimethylsilyl substituted benzimidazole compounds. The objectives of this study were to synthesize and elucidate the crystal structure of the title compound, 1-benzyl-3-trimethylsilylmethylbenzimidazolium chloride monohydrate, (I).

In the title molecule, (Fig. 1), the benzimidazole ring system (N1/N2/C1–C7) is approximately planar, with maximum deviations of -0.022 (2) Å for C6, -0.018 (2) for C1 and 0.015 (2) for C7. The benzimidazole (N1/N2/C1–C7) and phenyl (C9–C14) systems make an angle of 74.80 (12)°. The values of the geometric parameters in (I) are comparable with those observed for other similar compounds (Akkurt et al., 2008, 2010). The average value of the Si—C bond length is 1.854 (4) Å. The angles around the Si atoms with a distorted tetrahedral geometry rang from 105.86 (16)° to 111.81 (16)°.

The crystal packing of (I) is stabilized by O—H···Cl, C—H···Cl and C—H···π interactions between symmetry-related molecules (Fig. 2 and Table 1), together with π-π stacking interactions between imidazolium and benzene (Table 2).

Related literature top

For general background to benzimidazole compounds and for the biological activity of related structures, see: Galal et al. (2009); Huang et al. (2006); Küçükbay & Durmaz (1997); Küçükbay et al. (1995, 2003, 2004, 2010); Lukevics et al. (2001); Singh & Lown (2000); Tavman et al. (2005); Turner & Denny (1996); Williams et al. (2002); Yılmaz & Küçükbay (2009); Çetinkaya et al. (1996). For similar structures, see: Akkurt et al. (2008, 2010).

Experimental top

A mixture of 1-trimethylsilylmethylbenzimidazole (1.02 g, 5 mmol) and benzyl chloride (0.60 cm³, 5 mmol) in dimethylformamide (5 ml) was refluxed for 3 h. The mixture was then cooled and the volatiles were removed in vacuo. The residue was crystallized from a dimethylformamide/ethanol (1:1). White crystals of the title compound (1.36 g, 82%) were obtained, m.p. 425–426 K; ν_(CN) = 1553 cm^-1. Anal. Found: C 61.64, H 7.19, N 7.93%. Calculated for C₁₈H₂₅ClN₂OSi: C 61.96, H 7.22, N 8.03%. ¹H NMR (δ, DMSO-d₆): 10.21 (s, 1H, NCHN), 8.11 - 7.59 (m, 4H, C₆H₄), 7.56–7.33 (m, 5H, C₆H₅), 5.86 (s, 2H, CH₂ benzyl), 4.30 (s, 2H, CH₂Si) and 0.14 [s, 9H, (CH₃)₃Si]. ¹³C NMR (δ, DMSO-d₆): 141.6 (NCHN), 134.6, 132.1, 130.8, 129.1, 128.8 and 128.3 (C₆H₄), 126.8, 126.5, 114.3 and 113.9 (C₆H₅), 49.8 (CH₂ benzyl), 38.1(CH₂Si) and -2.5 [(CH₃)₃Si].

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. View of the title molecule in the asymmetric unit, with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii and H bonds are shown as dashed lines.
	Fig. 2. View of the packing and hydrogen bonding interactions of (I) down the b axis. All hydrogen atoms not involved in hydrogen bonding have been omitted for clarity.

1-Benzyl-3-[(trimethylsilyl)methyl]benzimidazolium chloride monohydrate top

Crystal data top

C₁₈H₂₃N₂Si⁺·Cl⁻·H₂O	Z = 2
M_r = 348.94	F(000) = 372
Triclinic, P1	D_x = 1.203 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3592 (7) Å	Cell parameters from 28124 reflections
b = 10.9500 (9) Å	θ = 2.1–28.0°
c = 11.0522 (8) Å	µ = 0.27 mm⁻¹
α = 117.594 (6)°	T = 296 K
β = 103.295 (6)°	Prism, colourless
γ = 92.094 (6)°	0.57 × 0.50 × 0.36 mm
V = 963.39 (15) Å³

Data collection top

Stoe IPDS 2 diffractometer	3987 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	3241 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.029
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.5°, θ_min = 2.1°
ω scans	h = −11→11
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −13→12
T_min = 0.859, T_max = 0.909	l = −13→13
12149 measured reflections

Refinement top

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0637P)² + 0.2683P] where P = (F_o² + 2F_c²)/3
3987 reflections	(Δ/σ)_max < 0.001
211 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₈H₂₃N₂Si⁺·Cl⁻·H₂O	γ = 92.094 (6)°
M_r = 348.94	V = 963.39 (15) Å³
Triclinic, P1	Z = 2
a = 9.3592 (7) Å	Mo Kα radiation
b = 10.9500 (9) Å	µ = 0.27 mm⁻¹
c = 11.0522 (8) Å	T = 296 K
α = 117.594 (6)°	0.57 × 0.50 × 0.36 mm
β = 103.295 (6)°

Data collection top

Stoe IPDS 2 diffractometer	3987 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	3241 reflections with I > 2σ(I)
T_min = 0.859, T_max = 0.909	R_int = 0.029
12149 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.07	Δρ_max = 0.32 e Å⁻³
3987 reflections	Δρ_min = −0.32 e Å⁻³
211 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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

	x	y	z	U_iso*/U_eq
Si1	0.53328 (7)	0.20172 (7)	0.79168 (6)	0.05705 (19)
N1	0.72385 (17)	0.36741 (17)	0.52896 (17)	0.0466 (4)
N2	0.59349 (17)	0.36730 (17)	0.66907 (17)	0.0466 (4)
C1	0.4923 (2)	0.33506 (19)	0.54087 (19)	0.0428 (4)
C2	0.3377 (2)	0.3101 (2)	0.4971 (2)	0.0521 (5)
H2	0.2816	0.3104	0.5566	0.063*
C3	0.2721 (2)	0.2847 (2)	0.3611 (2)	0.0587 (5)
H3	0.1688	0.2667	0.3276	0.070*
C4	0.3560 (2)	0.2853 (3)	0.2717 (2)	0.0592 (5)
H4	0.3071	0.2682	0.1806	0.071*
C5	0.5084 (2)	0.3104 (2)	0.3150 (2)	0.0532 (5)
H5	0.5641	0.3111	0.2555	0.064*
C6	0.57570 (19)	0.33479 (19)	0.4512 (2)	0.0432 (4)
C7	0.7293 (2)	0.3855 (2)	0.6574 (2)	0.0505 (5)
H7	0.8165	0.4079	0.7293	0.061*
C8	0.8534 (2)	0.3833 (2)	0.4794 (2)	0.0547 (5)
H8A	0.9413	0.4273	0.5602	0.066*
H8B	0.8371	0.4442	0.4377	0.066*
C9	0.8803 (2)	0.2461 (2)	0.3720 (2)	0.0510 (5)
C10	0.8520 (3)	0.2111 (3)	0.2308 (3)	0.0717 (7)
H10	0.8171	0.2741	0.2014	0.086*
C11	0.8748 (3)	0.0831 (4)	0.1329 (3)	0.0935 (10)
H11	0.8546	0.0600	0.0377	0.112*
C12	0.9272 (3)	−0.0100 (3)	0.1753 (4)	0.0947 (10)
H12	0.9404	−0.0970	0.1089	0.114*
C13	0.9600 (3)	0.0255 (3)	0.3158 (4)	0.0909 (10)
H13	0.9980	−0.0367	0.3451	0.109*
C14	0.9372 (3)	0.1527 (3)	0.4141 (3)	0.0700 (7)
H14	0.9602	0.1760	0.5095	0.084*
C15	0.5549 (3)	0.3754 (2)	0.7947 (2)	0.0549 (5)
H15A	0.4625	0.4122	0.8003	0.066*
H15B	0.6320	0.4406	0.8796	0.066*
C16	0.3837 (3)	0.0757 (3)	0.6328 (3)	0.0812 (8)
H16A	0.4063	0.0662	0.5487	0.122*
H16B	0.2907	0.1090	0.6377	0.122*
H16C	0.3767	−0.0135	0.6297	0.122*
C17	0.4849 (4)	0.2374 (4)	0.9569 (3)	0.1001 (10)
H17A	0.4744	0.1524	0.9619	0.150*
H17B	0.3928	0.2732	0.9569	0.150*
H17C	0.5624	0.3050	1.0376	0.150*
C18	0.7121 (3)	0.1391 (3)	0.7877 (3)	0.0899 (9)
H18A	0.7028	0.0478	0.7796	0.135*
H18B	0.7869	0.2023	0.8737	0.135*
H18C	0.7403	0.1344	0.7076	0.135*
O1	0.9113 (3)	0.6314 (2)	0.9603 (2)	0.1024 (7)
H1A	0.9910	0.6000	0.9420	0.154*
H1B	0.9090	0.6350	1.0380	0.154*
Cl1	1.14370 (9)	0.44812 (10)	0.80296 (8)	0.0961 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Si1	0.0616 (4)	0.0668 (4)	0.0477 (3)	0.0106 (3)	0.0191 (3)	0.0301 (3)
N1	0.0349 (8)	0.0565 (9)	0.0533 (9)	0.0048 (7)	0.0145 (7)	0.0295 (8)
N2	0.0448 (9)	0.0524 (9)	0.0460 (8)	0.0074 (7)	0.0162 (7)	0.0251 (7)
C1	0.0401 (9)	0.0458 (9)	0.0466 (9)	0.0086 (7)	0.0162 (8)	0.0238 (8)
C2	0.0404 (10)	0.0611 (12)	0.0632 (12)	0.0110 (9)	0.0240 (9)	0.0324 (10)
C3	0.0358 (10)	0.0717 (14)	0.0673 (13)	0.0081 (9)	0.0120 (9)	0.0339 (11)
C4	0.0471 (12)	0.0770 (14)	0.0527 (11)	0.0088 (10)	0.0087 (9)	0.0333 (11)
C5	0.0486 (11)	0.0686 (13)	0.0516 (11)	0.0106 (9)	0.0193 (9)	0.0340 (10)
C6	0.0343 (9)	0.0484 (10)	0.0507 (10)	0.0068 (7)	0.0145 (8)	0.0260 (8)
C7	0.0418 (10)	0.0554 (11)	0.0511 (11)	0.0031 (8)	0.0079 (8)	0.0260 (9)
C8	0.0360 (10)	0.0667 (13)	0.0736 (13)	0.0050 (9)	0.0216 (9)	0.0412 (11)
C9	0.0311 (9)	0.0671 (12)	0.0673 (12)	0.0090 (8)	0.0197 (9)	0.0400 (10)
C10	0.0529 (13)	0.1023 (19)	0.0737 (15)	0.0312 (13)	0.0236 (12)	0.0498 (15)
C11	0.0647 (17)	0.126 (3)	0.0702 (17)	0.0308 (17)	0.0212 (14)	0.0299 (17)
C12	0.0684 (18)	0.0793 (19)	0.120 (3)	0.0195 (15)	0.0432 (18)	0.0266 (18)
C13	0.087 (2)	0.088 (2)	0.146 (3)	0.0402 (16)	0.069 (2)	0.077 (2)
C14	0.0671 (15)	0.0864 (17)	0.0943 (18)	0.0279 (13)	0.0444 (14)	0.0631 (15)
C15	0.0599 (12)	0.0622 (12)	0.0420 (10)	0.0129 (10)	0.0203 (9)	0.0217 (9)
C16	0.0781 (18)	0.0771 (17)	0.0790 (17)	−0.0077 (13)	0.0151 (14)	0.0347 (14)
C17	0.142 (3)	0.111 (2)	0.0703 (17)	0.022 (2)	0.0513 (19)	0.0526 (17)
C18	0.0818 (19)	0.093 (2)	0.088 (2)	0.0247 (16)	0.0135 (16)	0.0423 (17)
O1	0.1114 (17)	0.0974 (15)	0.0822 (13)	0.0288 (13)	0.0144 (12)	0.0355 (12)
Cl1	0.0818 (5)	0.1278 (7)	0.0780 (5)	0.0348 (4)	0.0259 (4)	0.0465 (4)

Geometric parameters (Å, º) top

Si1—C18	1.834 (3)	C9—C10	1.378 (3)
Si1—C17	1.850 (3)	C9—C14	1.383 (3)
Si1—C16	1.852 (3)	C10—C11	1.380 (4)
Si1—C15	1.890 (2)	C10—H10	0.9300
N1—C7	1.328 (3)	C11—C12	1.368 (5)
N1—C6	1.386 (2)	C11—H11	0.9300
N1—C8	1.476 (2)	C12—C13	1.367 (5)
N2—C7	1.324 (2)	C12—H12	0.9300
N2—C1	1.387 (2)	C13—C14	1.376 (4)
N2—C15	1.478 (2)	C13—H13	0.9300
C1—C2	1.389 (3)	C14—H14	0.9300
C1—C6	1.394 (2)	C15—H15A	0.9700
C2—C3	1.374 (3)	C15—H15B	0.9700
C2—H2	0.9300	C16—H16A	0.9600
C3—C4	1.398 (3)	C16—H16B	0.9600
C3—H3	0.9300	C16—H16C	0.9600
C4—C5	1.369 (3)	C17—H17A	0.9600
C4—H4	0.9300	C17—H17B	0.9600
C5—C6	1.384 (3)	C17—H17C	0.9600
C5—H5	0.9300	C18—H18A	0.9600
C7—H7	0.9300	C18—H18B	0.9600
C8—C9	1.497 (3)	C18—H18C	0.9600
C8—H8A	0.9700	O1—H1A	0.8598
C8—H8B	0.9700	O1—H1B	0.8466

C18—Si1—C17	111.82 (16)	C14—C9—C8	120.0 (2)
C18—Si1—C16	110.58 (15)	C9—C10—C11	120.5 (3)
C17—Si1—C16	110.93 (16)	C9—C10—H10	119.8
C18—Si1—C15	107.44 (14)	C11—C10—H10	119.8
C17—Si1—C15	105.86 (13)	C12—C11—C10	120.2 (3)
C16—Si1—C15	110.04 (12)	C12—C11—H11	119.9
C7—N1—C6	108.20 (15)	C10—C11—H11	119.9
C7—N1—C8	125.70 (17)	C13—C12—C11	119.7 (3)
C6—N1—C8	126.08 (16)	C13—C12—H12	120.1
C7—N2—C1	108.16 (15)	C11—C12—H12	120.1
C7—N2—C15	126.39 (17)	C12—C13—C14	120.4 (3)
C1—N2—C15	125.43 (16)	C12—C13—H13	119.8
N2—C1—C2	131.97 (17)	C14—C13—H13	119.8
N2—C1—C6	106.56 (16)	C13—C14—C9	120.4 (3)
C2—C1—C6	121.45 (18)	C13—C14—H14	119.8
C3—C2—C1	116.40 (18)	C9—C14—H14	119.8
C3—C2—H2	121.8	N2—C15—Si1	113.64 (13)
C1—C2—H2	121.8	N2—C15—H15A	108.8
C2—C3—C4	122.03 (19)	Si1—C15—H15A	108.8
C2—C3—H3	119.0	N2—C15—H15B	108.8
C4—C3—H3	119.0	Si1—C15—H15B	108.8
C5—C4—C3	121.6 (2)	H15A—C15—H15B	107.7
C5—C4—H4	119.2	Si1—C16—H16A	109.5
C3—C4—H4	119.2	Si1—C16—H16B	109.5
C4—C5—C6	116.92 (18)	H16A—C16—H16B	109.5
C4—C5—H5	121.5	Si1—C16—H16C	109.5
C6—C5—H5	121.5	H16A—C16—H16C	109.5
C5—C6—N1	131.92 (17)	H16B—C16—H16C	109.5
C5—C6—C1	121.62 (17)	Si1—C17—H17A	109.5
N1—C6—C1	106.41 (16)	Si1—C17—H17B	109.5
N2—C7—N1	110.68 (17)	H17A—C17—H17B	109.5
N2—C7—H7	124.7	Si1—C17—H17C	109.5
N1—C7—H7	124.7	H17A—C17—H17C	109.5
N1—C8—C9	112.22 (16)	H17B—C17—H17C	109.5
N1—C8—H8A	109.2	Si1—C18—H18A	109.5
C9—C8—H8A	109.2	Si1—C18—H18B	109.5
N1—C8—H8B	109.2	H18A—C18—H18B	109.5
C9—C8—H8B	109.2	Si1—C18—H18C	109.5
H8A—C8—H8B	107.9	H18A—C18—H18C	109.5
C10—C9—C14	118.7 (2)	H18B—C18—H18C	109.5
C10—C9—C8	121.3 (2)	H1A—O1—H1B	107.0

C7—N2—C1—C2	−178.0 (2)	C15—N2—C7—N1	178.44 (17)
C15—N2—C1—C2	3.6 (3)	C6—N1—C7—N2	−0.3 (2)
C7—N2—C1—C6	0.1 (2)	C8—N1—C7—N2	178.18 (18)
C15—N2—C1—C6	−178.27 (17)	C7—N1—C8—C9	109.6 (2)
N2—C1—C2—C3	178.1 (2)	C6—N1—C8—C9	−72.2 (2)
C6—C1—C2—C3	0.2 (3)	N1—C8—C9—C10	108.7 (2)
C1—C2—C3—C4	−0.6 (3)	N1—C8—C9—C14	−72.5 (2)
C2—C3—C4—C5	0.4 (4)	C14—C9—C10—C11	2.3 (4)
C3—C4—C5—C6	0.2 (3)	C8—C9—C10—C11	−178.8 (2)
C4—C5—C6—N1	−177.7 (2)	C9—C10—C11—C12	−0.5 (4)
C4—C5—C6—C1	−0.6 (3)	C10—C11—C12—C13	−1.5 (5)
C7—N1—C6—C5	177.7 (2)	C11—C12—C13—C14	1.7 (5)
C8—N1—C6—C5	−0.7 (3)	C12—C13—C14—C9	0.2 (4)
C7—N1—C6—C1	0.3 (2)	C10—C9—C14—C13	−2.2 (3)
C8—N1—C6—C1	−178.13 (17)	C8—C9—C14—C13	179.0 (2)
N2—C1—C6—C5	−177.97 (18)	C7—N2—C15—Si1	−91.7 (2)
C2—C1—C6—C5	0.4 (3)	C1—N2—C15—Si1	86.4 (2)
N2—C1—C6—N1	−0.2 (2)	C18—Si1—C15—N2	60.61 (19)
C2—C1—C6—N1	178.10 (18)	C17—Si1—C15—N2	−179.77 (18)
C1—N2—C7—N1	0.1 (2)	C16—Si1—C15—N2	−59.84 (19)

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···Cl1	0.86	2.45	3.257 (2)	157
O1—H1B···Cl1ⁱ	0.85	2.45	3.250 (3)	158
C7—H7···O1	0.93	2.51	3.170 (3)	128
C8—H8A···Cl1	0.97	2.81	3.703 (2)	153
C3—H3···Cg3ⁱⁱ	0.93	2.69	3.526 (2)	151

Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₃N₂Si⁺·Cl⁻·H₂O
M_r	348.94
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	9.3592 (7), 10.9500 (9), 11.0522 (8)
α, β, γ (°)	117.594 (6), 103.295 (6), 92.094 (6)
V (Å³)	963.39 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.57 × 0.50 × 0.36

Data collection
Diffractometer	Stoe IPDS 2 diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.859, 0.909
No. of measured, independent and observed [I > 2σ(I)] reflections	12149, 3987, 3241
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.135, 1.07
No. of reflections	3987
No. of parameters	211
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.32

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···Cl1	0.86	2.45	3.257 (2)	157.4
O1—H1B···Cl1ⁱ	0.85	2.45	3.250 (3)	157.7
C7—H7···O1	0.93	2.51	3.170 (3)	128.1
C8—H8A···Cl1	0.97	2.81	3.703 (2)	153.2
C3—H3···Cg3ⁱⁱ	0.93	2.69	3.526 (2)	151.0

Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) x−1, y, z.

π–π stacking in the title compound (Å, °). top

Cg1 is the centroid of the N1, C6, C1, N2, C7 ring and Cg2 is the centroid of C1 to C6 ring. Offset is the angle between the centroid-to-centroid and plane-to-plane vectors.

	Centroid–centroid	plane–plane	offset
Cg1···Cg2ⁱ	3.5690 (15)	3.430 (1)	16.0
Cg2···Cg2ⁱ	3.7223 (14)	3.446 (1)	22.2

Symmetry code: (i) 1-x, 1-y, 1-z.

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund). HK & NŞ also thank the İnönü University Research Fund (BAPB-2008–60) for financial support of this study.

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Volume 66| Part 7| July 2010| Pages o1770-o1771

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