11-[Bis(tri­methyl­sil­yl)amino]-2,4-bis­(tri­methyl­sil­yl)-7,8,9,10-tetra­hydro-6H-cyclo­hepta­[1,2-b]quinoline

Çelik, Í.; Akkurt, M.; Ekiz, M.; Tutar, A.; Ökten, S.; Ersanlı, C.C.

doi:10.1107/S2414314617008884

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 6| June 2017| x170888

https://doi.org/10.1107/S2414314617008884

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11-[Bis(trimethylsilyl)amino]-2,4-bis(trimethylsilyl)-7,8,9,10-tetrahydro-6H-cyclohepta[1,2-b]quinoline

Ísmail Çelik,^a Mehmet Akkurt,^b ^* Makbule Ekiz,^c,^d Ahmet Tutar,^d Salih Ökten ^e and Cem Cüneyt Ersanlı ^f

^aDepartment of Physics, Faculty of Sciences, Cumhuriyet University, 58140 Sivas, Turkey, ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^cDepartment of Chemistry, Faculty of Art and Science, Düzce University, 81620 Düzce, Turkey, ^dDepartment of Chemistry, Faculty of Art and Science, Sakarya University, Serdivan, 54187 Sakarya, Turkey, ^eDepartment of Maths and Science Education, Faculty of Education, Kırıkkale University, Yahşihan, 71450 Kırıkkale, Turkey, and ^fDepartment of Physics, Faculty of Arts and Sciences, Sinop University, 57010 Sinop, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

Edited by E. R. T. Tiekink, Sunway University, Malaysia (Received 11 June 2017; accepted 14 June 2017; online 16 June 2017)

In the title compound, C₂₆H₄₈N₂Si₄, the cycloheptane ring adopts a chair conformation, while the quinolinyl ring system is almost planar [maximum deviation = 0.040 (3) Å for one of the C atoms carrying a Me₃Si group]. In the crystal, in the absence of classical hydrogen bonding, the packing is dominated by van der Waals forces. One of the N-bound trimethylsilyl groups is disordered by rotation about the C—SiMe₃ bond, and was modelled over two sets of sites in the ratio 0.873 (8):0.127 (8).

Keywords: crystal structure; cycloheptane ring; quinoline derivative.

CCDC reference: 1556094

Structure description

Tacrine (9-amino-1,2,3,4-tetrahydroacridine) inhibits acetylcholinesterase, and has been used as a drug for treating Alzheimer's disease (Recanatini et al., 2000 ; Peçanha et al., 2001 ; Katzman, 1986 ; Shutske et al., 1988 ) since 1993. However, serious side-effects have restricted its use against this disease (McKenna et al., 1997 ; da Costa et al., 2009 ). In recent years, several groups have focused upon synthesizing new tacrine derivatives and exploring their inhibitory effects on cancer cell lines and acetylcholinesterase in the desire to minimize side effects.

The Friedländer reaction is a well known method for synthesizing quinolines and hetero bicyclic aromatics with N-functionality (Peçanha et al., 2001; Zong et al., 2006 ). 9-Amino-1,2,3,4-tetrahydroacridine-1-ol, an effective anti-Alzheimer's agent, has been prepared by a copper-assisted Friedländer method (Shutske et al., 1989 ). A recent study (Ekiz et al., 2016 ) demonstrated a novel and convenient approach to prepare tacrine derivatives expanding on the restricted studies in the literature. In this study we present the structure of 11-[bis(trimethylsilyl)amino]-2,4-bis(trimethylsilyl)-7,8,9,10-tetrahydro-6H-cyclohepta[1,2-b] quinoline.

As shown in Fig. 1, the cycloheptane ring of the title molecule adopts a chair conformation with puckering parameters Q_T = 0.781 (4) Å, φ(2) 51.3 (5)° and φ(3) = 77.1 (3)°, while the quinoline ring system is almost planar with maximum deviations of 0.040 (3) Å for atom C13 and −0.037 (3) Å for atom C8. The Si3—N2—Si4 angle in the amino-di(trimethylsilyl) group is wide at 124.33 (15)°. Generally, the observed bond lengths are comparable to those reported for the similar compounds (Glöcklhofer et al., 2014 ; Sparrow et al., 2012 ; Akkurt et al., 2010 ).

Figure 1
View of the title compound, showing the atom-numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level. The minor component of the disordered Me₃Si group has been omitted.

In the crystal, in the absence of classical hydrogen bonds, the packing of the molecules is controlled by van der Waals forces (Fig. 2).

Figure 2
View of the packing of the title compound down the a axis.

Synthesis and crystallization

The title compound was prepared according to a reported procedure (Ekiz et al., 2016). Colourless crystals suitable for X-ray diffraction were obtained by slow evaporation from its hexane/chloroform (50:50) solution.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. In the title molecule, each methyl group of one the N2-bound trimethylsilyl groups is disordered over two sites, in a 0.873 (8): 0.127 (8) ratio. The Si3—methyl bond lengths were restrained to be equal with a standard uncertainty value = 0.02 Å.

Table 1
Experimental details

Crystal data
Chemical formula	C₂₆H₄₈N₂Si₄
M_r	501.02
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	13.4760 (14), 11.5597 (11), 20.883 (2)
β (°)	100.614 (5)
V (Å³)	3197.5 (5)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.20
Crystal size (mm)	0.15 × 0.12 × 0.11

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003 )
T_min, T_max	0.678, 0.740
No. of measured, independent and observed [I > 2σ(I)] reflections	56997, 6468, 4643
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.630

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.078, 0.166, 1.19
No. of reflections	6468
No. of parameters	299
No. of restraints	15
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.34
Computer programs: APEX2 and SAINT (Bruker, 2007 ), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), ORTEP-3 for Windows (Farrugia, 2012 ), PLATON (Spek, 2009 ) and PARST (Nardelli, 1995 ).

Structural data

CCDC reference: 1556094

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314617008884/tk4033sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617008884/tk4033Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617008884/tk4033Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009) and PARST (Nardelli, 1995).

11-[Bis(trimethylsilyl)amino]-2,4-bis(trimethylsilyl)-7,8,9,10-tetrahydro-6H-cyclohepta[1,2-b]quinoline top

Crystal data top

C₂₆H₄₈N₂Si₄	F(000) = 1096
M_r = 501.02	D_x = 1.041 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9086 reflections
a = 13.4760 (14) Å	θ = 2.9–26.5°
b = 11.5597 (11) Å	µ = 0.20 mm⁻¹
c = 20.883 (2) Å	T = 296 K
β = 100.614 (5)°	Prism, colourless
V = 3197.5 (5) Å³	0.15 × 0.12 × 0.11 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	4643 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.068
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	θ_max = 26.6°, θ_min = 2.9°
T_min = 0.678, T_max = 0.740	h = −16→16
56997 measured reflections	k = −14→14
6468 independent reflections	l = −26→26

Refinement top

Refinement on F²	15 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.078	w = 1/[σ²(F_o²) + (0.0279P)² + 4.8053P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.166	(Δ/σ)_max = 0.001
S = 1.19	Δρ_max = 0.27 e Å⁻³
6468 reflections	Δρ_min = −0.34 e Å⁻³
299 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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 > 2sigma(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.

All H atoms were placed in idealized positions and refined as riding atoms with C—H bond lengths fixed to 0.93–0.97 Å, and with U_iso(H) = 1.2–1.5U_eq(C).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Si1	0.20359 (9)	0.87480 (8)	0.47603 (5)	0.0498 (3)
Si2	0.11596 (8)	0.40010 (9)	0.41068 (5)	0.0504 (3)
Si3	0.46955 (9)	0.31878 (9)	0.62008 (6)	0.0565 (4)
Si4	0.29921 (9)	0.37413 (9)	0.69699 (5)	0.0537 (3)
N1	0.3448 (2)	0.7656 (2)	0.58641 (13)	0.0403 (9)
N2	0.3825 (2)	0.4130 (2)	0.64494 (13)	0.0411 (9)
C1	0.4295 (2)	0.6191 (3)	0.65948 (15)	0.0383 (10)
C2	0.5063 (3)	0.5961 (3)	0.72000 (18)	0.0540 (12)
C3	0.6139 (3)	0.6285 (4)	0.7141 (2)	0.0681 (16)
C4	0.6403 (3)	0.7561 (4)	0.7239 (2)	0.0750 (17)
C5	0.5779 (3)	0.8377 (4)	0.6755 (2)	0.0677 (17)
C6	0.4654 (3)	0.8352 (3)	0.67596 (19)	0.0535 (14)
C7	0.4103 (3)	0.7357 (3)	0.63832 (16)	0.0394 (10)
C8	0.3757 (2)	0.5318 (3)	0.62370 (15)	0.0365 (10)
C9	0.3072 (2)	0.5611 (2)	0.56529 (15)	0.0323 (9)
C10	0.2934 (2)	0.6801 (3)	0.54910 (15)	0.0344 (9)
C11	0.2246 (3)	0.7158 (3)	0.49251 (16)	0.0390 (10)
C12	0.1755 (3)	0.6304 (3)	0.45336 (16)	0.0427 (11)
C13	0.1882 (3)	0.5101 (3)	0.46656 (16)	0.0398 (10)
C14	0.2526 (2)	0.4788 (3)	0.52293 (15)	0.0375 (10)
C15	0.1850 (5)	0.2602 (4)	0.4183 (3)	0.118 (3)
C16	−0.0093 (4)	0.3801 (6)	0.4302 (3)	0.140 (3)
C17	0.1043 (5)	0.4514 (5)	0.3253 (2)	0.102 (2)
C18	0.1013 (4)	0.8889 (4)	0.4031 (2)	0.097 (2)
C19	0.1606 (4)	0.9486 (4)	0.5449 (2)	0.0740 (17)
C20	0.3197 (4)	0.9444 (4)	0.4585 (3)	0.086 (2)
C21	0.5034 (6)	0.3687 (7)	0.5443 (4)	0.121 (4)	0.873 (8)
C21A	0.450 (4)	0.307 (5)	0.5296 (8)	0.121 (4)	0.127 (8)
C22	0.5879 (4)	0.3074 (6)	0.6830 (4)	0.106 (3)	0.873 (8)
C22A	0.6023 (15)	0.371 (4)	0.631 (3)	0.106 (3)	0.127 (8)
C23	0.4138 (5)	0.1719 (4)	0.6112 (4)	0.088 (3)	0.873 (8)
C23A	0.465 (4)	0.1645 (18)	0.642 (3)	0.088 (3)	0.127 (8)
C24	0.2436 (4)	0.5072 (4)	0.7259 (3)	0.094 (2)
C25	0.3684 (4)	0.2976 (5)	0.7697 (2)	0.093 (2)
C26	0.1928 (4)	0.2838 (4)	0.6554 (3)	0.0852 (19)
H2A	0.50450	0.51450	0.73060	0.0650*
H2B	0.48760	0.63910	0.75580	0.0650*
H3A	0.66020	0.58420	0.74600	0.0810*
H3B	0.62490	0.60570	0.67130	0.0810*
H4A	0.63230	0.77820	0.76750	0.0900*
H4B	0.71090	0.76620	0.72130	0.0900*
H5A	0.60230	0.91600	0.68480	0.0820*
H5B	0.58840	0.81820	0.63210	0.0820*
H6A	0.45560	0.83090	0.72070	0.0640*
H6B	0.43570	0.90720	0.65770	0.0640*
H12	0.13110	0.65260	0.41580	0.0510*
H14	0.26030	0.40070	0.53350	0.0450*
H15A	0.25080	0.27130	0.40800	0.1760*
H15B	0.19150	0.23210	0.46220	0.1760*
H15C	0.14820	0.20490	0.38880	0.1760*
H16A	−0.00300	0.35360	0.47430	0.2100*
H16B	−0.04500	0.45240	0.42530	0.2100*
H16C	−0.04580	0.32390	0.40120	0.2100*
H17A	0.17040	0.46190	0.31520	0.1530*
H17B	0.06780	0.39530	0.29630	0.1530*
H17C	0.06860	0.52370	0.32040	0.1530*
H18A	0.12160	0.85130	0.36660	0.1460*
H18B	0.04080	0.85330	0.41180	0.1460*
H18C	0.08880	0.96930	0.39330	0.1460*
H19A	0.10060	0.91170	0.55340	0.1110*
H19B	0.21260	0.94410	0.58300	0.1110*
H19C	0.14650	1.02830	0.53390	0.1110*
H20A	0.34110	0.90530	0.42280	0.1280*
H20B	0.30610	1.02410	0.44720	0.1280*
H20C	0.37220	0.93980	0.49630	0.1280*
H21A	0.55120	0.31620	0.53130	0.1810*	0.873 (8)
H21B	0.44400	0.37200	0.51100	0.1810*	0.873 (8)
H21C	0.53290	0.44440	0.55070	0.1810*	0.873 (8)
H21D	0.49840	0.25460	0.51760	0.1810*	0.127 (8)
H21E	0.38280	0.27810	0.51350	0.1810*	0.127 (8)
H21F	0.45710	0.38170	0.51120	0.1810*	0.127 (8)
H22A	0.63400	0.25520	0.66790	0.1590*	0.873 (8)
H22B	0.61860	0.38240	0.69020	0.1590*	0.873 (8)
H22C	0.57170	0.27890	0.72300	0.1590*	0.873 (8)
H22D	0.64340	0.31240	0.61610	0.1590*	0.127 (8)
H22E	0.60500	0.44040	0.60680	0.1590*	0.127 (8)
H22F	0.62710	0.38540	0.67660	0.1590*	0.127 (8)
H23A	0.46090	0.11920	0.59760	0.1320*	0.873 (8)
H23B	0.39890	0.14710	0.65230	0.1320*	0.873 (8)
H23C	0.35270	0.17340	0.57920	0.1320*	0.873 (8)
H23D	0.51700	0.12310	0.62570	0.1320*	0.127 (8)
H23E	0.47670	0.15720	0.68890	0.1320*	0.127 (8)
H23F	0.40060	0.13300	0.62400	0.1320*	0.127 (8)
H24A	0.19810	0.48620	0.75430	0.1420*
H24B	0.29660	0.55500	0.74910	0.1420*
H24C	0.20750	0.54900	0.68910	0.1420*
H25A	0.32220	0.27690	0.79770	0.1380*
H25B	0.39900	0.22900	0.75630	0.1380*
H25C	0.41990	0.34750	0.79280	0.1380*
H26A	0.14950	0.26470	0.68560	0.1280*
H26B	0.15510	0.32590	0.61930	0.1280*
H26C	0.21880	0.21400	0.63980	0.1280*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Si1	0.0707 (7)	0.0310 (5)	0.0446 (6)	0.0121 (5)	0.0024 (5)	0.0032 (4)
Si2	0.0573 (7)	0.0422 (5)	0.0494 (6)	−0.0058 (5)	0.0038 (5)	−0.0107 (5)
Si3	0.0516 (6)	0.0393 (5)	0.0780 (8)	0.0119 (5)	0.0106 (6)	0.0113 (5)
Si4	0.0669 (7)	0.0403 (5)	0.0559 (6)	−0.0046 (5)	0.0169 (5)	0.0087 (5)
N1	0.0456 (17)	0.0303 (13)	0.0430 (16)	−0.0026 (12)	0.0031 (13)	0.0007 (12)
N2	0.0441 (16)	0.0314 (14)	0.0453 (16)	0.0024 (12)	0.0016 (13)	0.0099 (12)
C1	0.0363 (18)	0.0391 (17)	0.0376 (17)	−0.0008 (14)	0.0018 (14)	0.0055 (14)
C2	0.054 (2)	0.050 (2)	0.050 (2)	−0.0032 (18)	−0.0110 (18)	0.0057 (17)
C3	0.050 (2)	0.076 (3)	0.070 (3)	−0.003 (2)	−0.011 (2)	−0.003 (2)
C4	0.054 (3)	0.080 (3)	0.084 (3)	−0.023 (2)	−0.006 (2)	−0.006 (3)
C5	0.067 (3)	0.065 (3)	0.066 (3)	−0.029 (2)	−0.001 (2)	−0.005 (2)
C6	0.064 (3)	0.0396 (19)	0.053 (2)	−0.0100 (18)	0.0003 (19)	−0.0045 (17)
C7	0.0415 (19)	0.0363 (17)	0.0397 (18)	−0.0044 (15)	0.0056 (15)	−0.0006 (14)
C8	0.0376 (18)	0.0309 (16)	0.0403 (17)	0.0018 (14)	0.0057 (14)	0.0051 (14)
C9	0.0332 (17)	0.0271 (15)	0.0363 (16)	0.0021 (13)	0.0053 (13)	0.0045 (12)
C10	0.0370 (17)	0.0307 (15)	0.0356 (16)	0.0019 (13)	0.0072 (14)	0.0018 (13)
C11	0.0457 (19)	0.0315 (16)	0.0384 (18)	0.0050 (14)	0.0041 (15)	0.0031 (14)
C12	0.047 (2)	0.0390 (18)	0.0384 (18)	0.0078 (16)	−0.0017 (15)	0.0013 (15)
C13	0.0410 (19)	0.0351 (17)	0.0419 (18)	0.0013 (14)	0.0043 (15)	−0.0022 (14)
C14	0.0397 (18)	0.0269 (15)	0.0465 (19)	0.0019 (13)	0.0093 (15)	0.0034 (14)
C15	0.167 (6)	0.056 (3)	0.115 (5)	0.020 (3)	−0.014 (4)	−0.025 (3)
C16	0.092 (4)	0.198 (7)	0.142 (6)	−0.075 (5)	0.055 (4)	−0.099 (5)
C17	0.151 (5)	0.090 (4)	0.056 (3)	−0.024 (4)	−0.004 (3)	−0.013 (3)
C18	0.136 (5)	0.058 (3)	0.077 (3)	0.034 (3)	−0.034 (3)	0.005 (2)
C19	0.093 (3)	0.057 (3)	0.073 (3)	0.023 (2)	0.018 (3)	−0.006 (2)
C20	0.116 (4)	0.047 (2)	0.102 (4)	0.003 (3)	0.041 (3)	0.018 (2)
C21	0.128 (7)	0.114 (6)	0.148 (6)	0.064 (5)	0.099 (6)	0.067 (5)
C21A	0.128 (7)	0.114 (6)	0.148 (6)	0.064 (5)	0.099 (6)	0.067 (5)
C22	0.072 (4)	0.088 (5)	0.145 (7)	0.035 (4)	−0.015 (4)	−0.005 (4)
C22A	0.072 (4)	0.088 (5)	0.145 (7)	0.035 (4)	−0.015 (4)	−0.005 (4)
C23	0.095 (5)	0.048 (3)	0.126 (6)	0.012 (3)	0.034 (4)	−0.008 (3)
C23A	0.095 (5)	0.048 (3)	0.126 (6)	0.012 (3)	0.034 (4)	−0.008 (3)
C24	0.112 (4)	0.066 (3)	0.124 (5)	−0.002 (3)	0.071 (4)	−0.006 (3)
C25	0.123 (5)	0.092 (4)	0.062 (3)	−0.011 (3)	0.016 (3)	0.029 (3)
C26	0.081 (3)	0.081 (3)	0.097 (4)	−0.028 (3)	0.025 (3)	0.005 (3)

Geometric parameters (Å, º) top

Si1—C11	1.882 (4)	C12—H12	0.9300
Si1—C18	1.864 (5)	C14—H14	0.9300
Si1—C19	1.854 (5)	C15—H15A	0.9600
Si1—C20	1.855 (6)	C15—H15B	0.9600
Si2—C13	1.873 (4)	C15—H15C	0.9600
Si2—C15	1.858 (5)	C16—H16A	0.9600
Si2—C16	1.823 (6)	C16—H16B	0.9600
Si2—C17	1.858 (4)	C16—H16C	0.9600
Si3—N2	1.748 (3)	C17—H17A	0.9600
Si3—C21	1.820 (8)	C17—H17B	0.9600
Si3—C22	1.875 (7)	C17—H17C	0.9600
Si3—C23	1.852 (5)	C18—H18A	0.9600
Si3—C21A	1.864 (17)	C18—H18B	0.9600
Si3—C22A	1.86 (3)	C18—H18C	0.9600
Si3—C23A	1.85 (3)	C19—H19A	0.9600
Si4—N2	1.759 (3)	C19—H19B	0.9600
Si4—C24	1.860 (5)	C19—H19C	0.9600
Si4—C25	1.854 (5)	C20—H20A	0.9600
Si4—C26	1.855 (6)	C20—H20B	0.9600
N1—C7	1.312 (4)	C20—H20C	0.9600
N1—C10	1.366 (4)	C21—H21A	0.9600
N2—C8	1.441 (4)	C21—H21B	0.9600
C1—C2	1.502 (5)	C21—H21C	0.9600
C1—C7	1.427 (5)	C21A—H21D	0.9600
C1—C8	1.379 (5)	C21A—H21E	0.9700
C2—C3	1.524 (6)	C21A—H21F	0.9600
C3—C4	1.522 (6)	C22—H22C	0.9600
C4—C5	1.518 (6)	C22—H22A	0.9600
C5—C6	1.518 (6)	C22—H22B	0.9600
C6—C7	1.509 (5)	C22A—H22E	0.9500
C8—C9	1.428 (4)	C22A—H22D	0.9600
C9—C10	1.421 (4)	C22A—H22F	0.9600
C9—C14	1.410 (4)	C23—H23C	0.9600
C10—C11	1.422 (5)	C23—H23A	0.9600
C11—C12	1.372 (5)	C23—H23B	0.9600
C12—C13	1.422 (5)	C23A—H23E	0.9700
C13—C14	1.376 (5)	C23A—H23D	0.9600
C2—H2A	0.9700	C23A—H23F	0.9500
C2—H2B	0.9700	C24—H24A	0.9600
C3—H3A	0.9700	C24—H24C	0.9600
C3—H3B	0.9700	C24—H24B	0.9600
C4—H4A	0.9700	C25—H25B	0.9600
C4—H4B	0.9700	C25—H25C	0.9600
C5—H5A	0.9700	C25—H25A	0.9600
C5—H5B	0.9700	C26—H26C	0.9600
C6—H6A	0.9700	C26—H26A	0.9600
C6—H6B	0.9700	C26—H26B	0.9600

C11—Si1—C18	107.38 (19)	Si2—C15—H15A	109.00
C11—Si1—C19	111.44 (18)	Si2—C15—H15B	109.00
C11—Si1—C20	110.8 (2)	Si2—C15—H15C	109.00
C18—Si1—C19	107.7 (2)	H15A—C15—H15B	109.00
C18—Si1—C20	108.9 (2)	H15A—C15—H15C	110.00
C19—Si1—C20	110.4 (2)	H15B—C15—H15C	109.00
C13—Si2—C15	110.1 (2)	Si2—C16—H16A	109.00
C13—Si2—C16	110.1 (2)	Si2—C16—H16B	109.00
C13—Si2—C17	108.9 (2)	Si2—C16—H16C	109.00
C15—Si2—C16	109.9 (3)	H16A—C16—H16B	110.00
C15—Si2—C17	108.2 (3)	H16A—C16—H16C	110.00
C16—Si2—C17	109.7 (3)	H16B—C16—H16C	109.00
N2—Si3—C21	110.5 (3)	Si2—C17—H17A	109.00
N2—Si3—C22	111.5 (2)	Si2—C17—H17B	109.00
N2—Si3—C23	108.6 (2)	Si2—C17—H17C	109.00
N2—Si3—C21A	111.7 (17)	H17A—C17—H17B	110.00
N2—Si3—C22A	116.4 (14)	H17A—C17—H17C	109.00
N2—Si3—C23A	118.3 (17)	H17B—C17—H17C	109.00
C21—Si3—C22	108.3 (3)	Si1—C18—H18A	109.00
C21—Si3—C23	111.5 (4)	Si1—C18—H18B	110.00
C22—Si3—C23	106.4 (3)	Si1—C18—H18C	109.00
C21A—Si3—C22A	96 (3)	H18A—C18—H18B	109.00
C21A—Si3—C23A	100 (3)	H18A—C18—H18C	109.00
C22A—Si3—C23A	111 (2)	H18B—C18—H18C	109.00
N2—Si4—C24	109.30 (19)	Si1—C19—H19A	109.00
N2—Si4—C25	110.3 (2)	Si1—C19—H19B	109.00
N2—Si4—C26	112.4 (2)	Si1—C19—H19C	109.00
C24—Si4—C25	107.5 (3)	H19A—C19—H19B	110.00
C24—Si4—C26	107.1 (2)	H19A—C19—H19C	110.00
C25—Si4—C26	110.1 (2)	H19B—C19—H19C	109.00
C7—N1—C10	118.3 (3)	Si1—C20—H20A	110.00
Si3—N2—Si4	124.33 (15)	Si1—C20—H20B	110.00
Si3—N2—C8	120.7 (2)	Si1—C20—H20C	110.00
Si4—N2—C8	115.0 (2)	H20A—C20—H20B	109.00
C2—C1—C7	119.0 (3)	H20A—C20—H20C	109.00
C2—C1—C8	122.6 (3)	H20B—C20—H20C	109.00
C7—C1—C8	118.4 (3)	Si3—C21—H21A	110.00
C1—C2—C3	114.0 (3)	Si3—C21—H21B	109.00
C2—C3—C4	115.4 (3)	Si3—C21—H21C	109.00
C3—C4—C5	115.2 (4)	H21A—C21—H21B	110.00
C4—C5—C6	114.5 (3)	H21A—C21—H21C	109.00
C5—C6—C7	114.0 (3)	H21B—C21—H21C	109.00
N1—C7—C1	124.1 (3)	Si3—C21A—H21E	109.00
N1—C7—C6	114.9 (3)	Si3—C21A—H21F	110.00
C1—C7—C6	121.0 (3)	H21D—C21A—H21E	109.00
N2—C8—C1	122.2 (3)	H21D—C21A—H21F	110.00
N2—C8—C9	118.9 (3)	H21E—C21A—H21F	109.00
C1—C8—C9	118.8 (3)	Si3—C21A—H21D	110.00
C8—C9—C10	117.9 (3)	H22A—C22—H22C	110.00
C8—C9—C14	123.8 (3)	Si3—C22—H22B	109.00
C10—C9—C14	118.3 (3)	H22B—C22—H22C	110.00
N1—C10—C9	122.3 (3)	Si3—C22—H22A	109.00
N1—C10—C11	116.7 (3)	Si3—C22—H22C	109.00
C9—C10—C11	121.0 (3)	H22A—C22—H22B	109.00
Si1—C11—C10	119.2 (3)	Si3—C22A—H22F	109.00
Si1—C11—C12	123.7 (3)	Si3—C22A—H22E	110.00
C10—C11—C12	117.1 (3)	Si3—C22A—H22D	109.00
C11—C12—C13	124.1 (3)	H22D—C22A—H22E	110.00
Si2—C13—C12	120.9 (3)	H22D—C22A—H22F	109.00
Si2—C13—C14	121.9 (3)	H22E—C22A—H22F	110.00
C12—C13—C14	117.2 (3)	H23B—C23—H23C	109.00
C9—C14—C13	122.2 (3)	H23A—C23—H23C	110.00
C1—C2—H2A	109.00	Si3—C23—H23B	109.00
C1—C2—H2B	109.00	Si3—C23—H23C	109.00
C3—C2—H2A	109.00	Si3—C23—H23A	109.00
C3—C2—H2B	109.00	H23A—C23—H23B	109.00
H2A—C2—H2B	108.00	Si3—C23A—H23F	110.00
C2—C3—H3A	108.00	H23D—C23A—H23E	109.00
C2—C3—H3B	108.00	Si3—C23A—H23E	109.00
C4—C3—H3A	108.00	Si3—C23A—H23D	109.00
C4—C3—H3B	108.00	H23E—C23A—H23F	109.00
H3A—C3—H3B	108.00	H23D—C23A—H23F	110.00
C3—C4—H4A	109.00	Si4—C24—H24B	109.00
C3—C4—H4B	108.00	Si4—C24—H24A	109.00
C5—C4—H4A	109.00	H24B—C24—H24C	110.00
C5—C4—H4B	108.00	H24A—C24—H24C	110.00
H4A—C4—H4B	107.00	Si4—C24—H24C	109.00
C4—C5—H5A	109.00	H24A—C24—H24B	110.00
C4—C5—H5B	109.00	Si4—C25—H25B	110.00
C6—C5—H5A	109.00	H25A—C25—H25C	109.00
C6—C5—H5B	109.00	Si4—C25—H25C	109.00
H5A—C5—H5B	108.00	H25A—C25—H25B	109.00
C5—C6—H6A	109.00	Si4—C25—H25A	109.00
C5—C6—H6B	109.00	H25B—C25—H25C	109.00
C7—C6—H6A	109.00	Si4—C26—H26C	109.00
C7—C6—H6B	109.00	H26A—C26—H26C	109.00
H6A—C6—H6B	108.00	H26B—C26—H26C	109.00
C11—C12—H12	118.00	H26A—C26—H26B	110.00
C13—C12—H12	118.00	Si4—C26—H26A	109.00
C9—C14—H14	119.00	Si4—C26—H26B	109.00
C13—C14—H14	119.00

C18—Si1—C11—C12	3.9 (4)	C2—C1—C8—N2	5.8 (5)
C19—Si1—C11—C12	121.6 (4)	C8—C1—C7—N1	−0.5 (5)
C20—Si1—C11—C12	−115.0 (4)	C7—C1—C8—N2	−173.5 (3)
C20—Si1—C11—C10	66.3 (4)	C7—C1—C8—C9	3.3 (4)
C18—Si1—C11—C10	−174.9 (3)	C2—C1—C7—C6	−0.3 (5)
C19—Si1—C11—C10	−57.2 (4)	C2—C1—C7—N1	−179.8 (3)
C17—Si2—C13—C14	−145.5 (3)	C8—C1—C2—C3	115.4 (4)
C15—Si2—C13—C14	−27.1 (4)	C2—C1—C8—C9	−177.4 (3)
C16—Si2—C13—C14	94.2 (4)	C1—C2—C3—C4	81.3 (4)
C16—Si2—C13—C12	−83.4 (4)	C2—C3—C4—C5	−61.1 (5)
C17—Si2—C13—C12	36.8 (4)	C3—C4—C5—C6	60.7 (5)
C15—Si2—C13—C12	155.3 (4)	C4—C5—C6—C7	−80.5 (4)
C21—Si3—N2—C8	−23.8 (4)	C5—C6—C7—C1	66.4 (5)
C21—Si3—N2—Si4	157.0 (3)	C5—C6—C7—N1	−114.2 (4)
C22—Si3—N2—Si4	−82.5 (3)	N2—C8—C9—C14	−6.8 (4)
C22—Si3—N2—C8	96.7 (3)	C1—C8—C9—C10	−3.8 (4)
C23—Si3—N2—C8	−146.4 (3)	C1—C8—C9—C14	176.3 (3)
C23—Si3—N2—Si4	34.5 (3)	N2—C8—C9—C10	173.1 (3)
C26—Si4—N2—C8	106.1 (3)	C14—C9—C10—C11	1.5 (4)
C25—Si4—N2—Si3	48.5 (3)	C10—C9—C14—C13	0.9 (4)
C25—Si4—N2—C8	−130.7 (3)	C8—C9—C10—C11	−178.5 (3)
C24—Si4—N2—Si3	166.5 (2)	C8—C9—C14—C13	−179.1 (3)
C26—Si4—N2—Si3	−74.7 (3)	C8—C9—C10—N1	1.6 (4)
C24—Si4—N2—C8	−12.8 (3)	C14—C9—C10—N1	−178.5 (3)
C10—N1—C7—C1	−1.8 (5)	C9—C10—C11—Si1	176.4 (2)
C7—N1—C10—C11	−178.7 (3)	N1—C10—C11—C12	177.6 (3)
C7—N1—C10—C9	1.2 (5)	C9—C10—C11—C12	−2.4 (5)
C10—N1—C7—C6	178.7 (3)	N1—C10—C11—Si1	−3.7 (4)
Si3—N2—C8—C9	90.8 (3)	Si1—C11—C12—C13	−177.7 (3)
Si4—N2—C8—C1	86.9 (3)	C10—C11—C12—C13	1.0 (6)
Si4—N2—C8—C9	−89.9 (3)	C11—C12—C13—C14	1.3 (6)
Si3—N2—C8—C1	−92.4 (3)	C11—C12—C13—Si2	179.0 (3)
C7—C1—C2—C3	−65.3 (4)	Si2—C13—C14—C9	−180.0 (2)
C8—C1—C7—C6	179.0 (3)	C12—C13—C14—C9	−2.2 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···N2	0.97	2.49	2.959 (4)	110
C14—H14···N2	0.93	2.60	2.914 (4)	101

Acknowledgements

The authors acknowledge the Scientific and Technological Research Application and Research Center, Sinop University, Turkey, for the use of the Bruker D8 QUEST diffractometer.

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