N (1)-(Thio-phen-2-ylmeth-yl)-N (3),N (3)-bis-[3-(thio-phen-2-yl-methyl-ammonio)-prop-yl]propane-1,3-di-ammonium hexa-fluorido-silicate methanol tris-olvate.

In the title compound, C24H40N4S3 (4+)·2SiF6 (2-)·3CH3OH, the central tertiary amine function is protonated and is connected to three thio-phen-2-yl-methyl-amino-n-propyl groups, forming the arms of a T-shaped cation that has two pockets. Each arm contains one protonated secondary amine function, and each pocket is occupied by one SiF6 (2-) anion bonded via two N-H⋯F inter-actions with the protonated amine group on the middle arm, while two methanol solvent mol-ecules are N-H⋯O hydrogen-bonded with the other secondary protonated amine groups on the side arms. Weak O-H⋯O and O-H⋯F hydrogen bonds between the solvent mol-ecules and between the solvent mol-ecules and the anions, respectively, are also observed. All three thio-phene groups in the arms are disordered over two sets of sites, with occupancy ratios of 0.828 (3):0.172 (3), 0.910 (2):0.090 (2) and 0.890 (3):0.110 (3).

Related literature

For background to polyamine-based mol­ecules, see: McKee et al. (2003 ▶); Hossain (2008 ▶); Mendy et al. (2010 ▶). For our previous work on this class of compound, see: Işıklan et al. (2011 ▶); Hossain et al. (2011 ▶). For related structures, see: Hossain et al. (2012 ▶); Pilate et al. (2010 ▶).

Experimental

Crystal data

C24H40N4S3 4+·2SiF6 2−·3CH4O

M = 861.09

Triclinic,

a = 8.4854 (4) Å

b = 12.5107 (6) Å

c = 18.9003 (10) Å

α = 89.024 (2)°

β = 87.750 (2)°

γ = 72.206 (3)°

V = 1908.94 (16) Å3

Z = 2

Mo Kα radiation

μ = 0.35 mm−1

T = 100 K

0.58 × 0.16 × 0.03 mm

Data collection

Bruker APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.822, T max = 0.990

25975 measured reflections

9447 independent reflections

7815 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.125

S = 1.00

9447 reflections

604 parameters

642 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.94 e Å−3

Δρmin = −0.80 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813029565/wm2779sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813029565/wm2779Isup2.hkl

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

C24H40N4S34+·2SiF62−·3CH4O	Z = 2
Mr = 861.09	F(000) = 900
Triclinic, P1	Dx = 1.498 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4854 (4) Å	Cell parameters from 9116 reflections
b = 12.5107 (6) Å	θ = 2.5–28.3°
c = 18.9003 (10) Å	µ = 0.35 mm−1
α = 89.024 (2)°	T = 100 K
β = 87.750 (2)°	Plate, colorless
γ = 72.206 (3)°	0.58 × 0.16 × 0.03 mm
V = 1908.94 (16) Å3

Bruker APEX CCD diffractometer	9447 independent reflections
Radiation source: fine-focus sealed tube	7815 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 28.3°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −11→11
Tmin = 0.822, Tmax = 0.990	k = −16→16
25975 measured reflections	l = −24→25

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.070P)2 + 1.560P] where P = (Fo2 + 2Fc2)/3
9447 reflections	(Δ/σ)max = 0.006
604 parameters	Δρmax = 0.94 e Å−3
642 restraints	Δρmin = −0.80 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.13157 (18)	0.16663 (12)	0.44971 (8)	0.0129 (3)
H1	0.025 (3)	0.1828 (19)	0.4645 (12)	0.015*
C2A	0.1602 (2)	0.27924 (14)	0.44162 (10)	0.0143 (3)
H2A1	0.1293	0.3205	0.4868	0.017*
H2A2	0.0876	0.3233	0.4048	0.017*
C3A	0.3400 (2)	0.26928 (15)	0.42114 (10)	0.0159 (3)
H3A1	0.4114	0.2399	0.4617	0.019*
H3A2	0.3790	0.2166	0.3811	0.019*
C4A	0.3505 (2)	0.38465 (15)	0.39995 (10)	0.0159 (3)
H4A1	0.2840	0.4119	0.3577	0.019*
H4A2	0.3044	0.4382	0.4390	0.019*
N5A	0.52685 (19)	0.37908 (13)	0.38383 (9)	0.0153 (3)
H5A1	0.570 (3)	0.376 (2)	0.4221 (10)	0.018*
H5A2	0.576 (3)	0.3214 (16)	0.3613 (11)	0.018*
C6A	0.53771 (19)	0.47655 (14)	0.34078 (9)	0.0168 (3)
H6A1	0.4614	0.5456	0.3623	0.020*
H6A2	0.4985	0.4697	0.2929	0.020*
C7A	0.7067 (2)	0.49026 (14)	0.33317 (11)	0.0174 (3)	0.828 (3)
S8A	0.77713 (7)	0.56389 (5)	0.39491 (3)	0.01999 (19)	0.828 (3)
C9A	0.9620 (3)	0.5433 (2)	0.34880 (15)	0.0206 (5)	0.828 (3)
H9A	1.0477	0.5719	0.3627	0.025*	0.828 (3)
C10A	0.9704 (3)	0.4808 (2)	0.28972 (15)	0.0222 (5)	0.828 (3)
H10A	1.0636	0.4598	0.2576	0.027*	0.828 (3)
C11A	0.8239 (4)	0.4505 (3)	0.28160 (17)	0.0210 (7)	0.828 (3)
H11A	0.8097	0.4064	0.2434	0.025*	0.828 (3)
C7A'	0.7048 (4)	0.4918 (4)	0.3297 (3)	0.0174 (3)	0.172 (3)
S8A'	0.8363 (4)	0.4256 (4)	0.2610 (2)	0.0204 (9)	0.172 (3)
C9A'	0.9851 (9)	0.4837 (8)	0.2850 (6)	0.0183 (15)	0.172 (3)
H9A'	1.0894	0.4708	0.2608	0.022*	0.172 (3)
C10M	0.9351 (12)	0.5504 (11)	0.3430 (7)	0.0186 (14)	0.172 (3)
H10M	1.0007	0.5898	0.3640	0.022*	0.172 (3)
C11M	0.7739 (10)	0.5543 (9)	0.3684 (5)	0.0202 (13)	0.172 (3)
H11M	0.7201	0.5965	0.4085	0.024*	0.172 (3)
C2B	0.2348 (2)	0.09184 (15)	0.50512 (9)	0.0154 (3)
H2B1	0.3507	0.0634	0.4866	0.018*
H2B2	0.1940	0.0263	0.5133	0.018*
C3B	0.2323 (2)	0.14949 (15)	0.57565 (9)	0.0145 (3)
H3B1	0.3094	0.1951	0.5731	0.017*
H3B2	0.1195	0.1996	0.5874	0.017*
C4B	0.2852 (2)	0.05860 (16)	0.63168 (10)	0.0192 (4)
H4B1	0.2107	0.0112	0.6318	0.023*
H4B2	0.3989	0.0102	0.6197	0.023*
N5B	0.2812 (2)	0.10644 (14)	0.70420 (9)	0.0183 (3)
H5B1	0.291 (3)	0.0564 (17)	0.7339 (11)	0.022*
H5B2	0.186 (2)	0.1499 (18)	0.7114 (13)	0.022*
C6B	0.4083 (2)	0.16507 (18)	0.71464 (9)	0.0241 (4)
H6B1	0.5163	0.1190	0.6940	0.029*
H6B2	0.3757	0.2379	0.6892	0.029*
C7B	0.42679 (18)	0.18499 (18)	0.79115 (10)	0.0218 (4)	0.910 (2)
S8B	0.36470 (9)	0.31908 (5)	0.82559 (4)	0.03128 (19)	0.910 (2)
C9B	0.4257 (3)	0.27031 (19)	0.90860 (11)	0.0291 (5)	0.910 (2)
H9B	0.4161	0.3169	0.9487	0.035*	0.910 (2)
C10B	0.4896 (3)	0.15638 (18)	0.90968 (11)	0.0249 (5)	0.910 (2)
H10B	0.5300	0.1139	0.9509	0.030*	0.910 (2)
C11B	0.4891 (5)	0.1083 (3)	0.84208 (15)	0.0276 (6)	0.910 (2)
H11B	0.5287	0.0298	0.8336	0.033*	0.910 (2)
C7B'	0.4050 (9)	0.1995 (7)	0.7902 (2)	0.0218 (4)	0.090 (2)
S8B'	0.4924 (16)	0.1029 (9)	0.8549 (3)	0.0307 (16)	0.090 (2)
C9B'	0.438 (2)	0.2041 (13)	0.9192 (5)	0.031 (2)	0.090 (2)
H9B'	0.4622	0.1903	0.9678	0.037*	0.090 (2)
C10N	0.357 (3)	0.3066 (11)	0.8918 (6)	0.0303 (19)	0.090 (2)
H10N	0.3172	0.3730	0.9193	0.036*	0.090 (2)
C11N	0.338 (2)	0.3031 (9)	0.8178 (6)	0.0279 (18)	0.090 (2)
H11N	0.2846	0.3672	0.7903	0.033*	0.090 (2)
C2C	0.1575 (2)	0.10067 (15)	0.38197 (9)	0.0153 (3)
H2C1	0.1239	0.0324	0.3908	0.018*
H2C2	0.2772	0.0762	0.3688	0.018*
C3C	0.0627 (2)	0.16447 (16)	0.31978 (10)	0.0182 (4)
H3C1	0.1074	0.2259	0.3044	0.022*
H3C2	−0.0560	0.1973	0.3333	0.022*
C4C	0.0845 (2)	0.07987 (17)	0.26041 (10)	0.0215 (4)
H4C1	0.2037	0.0386	0.2533	0.026*
H4C2	0.0265	0.0247	0.2744	0.026*
N5C	0.0187 (2)	0.13442 (16)	0.19252 (9)	0.0232 (4)
H5C1	−0.084 (2)	0.168 (2)	0.1948 (14)	0.028*
H5C2	0.063 (3)	0.1843 (19)	0.1787 (13)	0.028*
C6C	0.0497 (3)	0.04944 (17)	0.13373 (9)	0.0272 (4)
H6C1	0.1660	0.0004	0.1344	0.033*
H6C2	−0.0233	0.0017	0.1416	0.033*
C7C	0.0177 (3)	0.10602 (15)	0.06322 (10)	0.0279 (4)	0.890 (3)
S8C	0.18115 (8)	0.11894 (7)	0.01032 (3)	0.0321 (2)	0.890 (3)
C9C	0.0503 (3)	0.1870 (3)	−0.05466 (13)	0.0354 (6)	0.890 (3)
H9C	0.0857	0.2128	−0.0982	0.042*	0.890 (3)
C10C	−0.1108 (3)	0.1990 (3)	−0.03549 (15)	0.0361 (6)	0.890 (3)
H10C	−0.2017	0.2351	−0.0641	0.043*	0.890 (3)
C11C	−0.1271 (4)	0.1517 (3)	0.03181 (16)	0.0329 (7)	0.890 (3)
H11C	−0.2308	0.1521	0.0529	0.039*	0.890 (3)
C7C'	0.0154 (9)	0.1106 (7)	0.0647 (3)	0.0279 (4)	0.110 (3)
S8C'	−0.1832 (8)	0.1641 (9)	0.0348 (4)	0.0447 (16)	0.110 (3)
C9C'	−0.1166 (18)	0.2163 (16)	−0.0414 (6)	0.0363 (18)	0.110 (3)
H9C'	−0.1874	0.2559	−0.0772	0.044*	0.110 (3)
C10O	0.0513 (18)	0.194 (2)	−0.0437 (8)	0.0361 (17)	0.110 (3)
H10O	0.1122	0.2153	−0.0815	0.043*	0.110 (3)
C11O	0.1238 (15)	0.1333 (18)	0.0173 (7)	0.0342 (16)	0.110 (3)
H11O	0.2397	0.1108	0.0241	0.041*	0.110 (3)
Si1D	0.73108 (6)	0.23998 (4)	0.55231 (3)	0.01483 (11)
F1D	0.57427 (13)	0.35369 (9)	0.52832 (6)	0.0184 (2)
F2D	0.60821 (13)	0.15817 (9)	0.54819 (7)	0.0226 (2)
F3D	0.67788 (14)	0.26449 (10)	0.63891 (6)	0.0230 (2)
F4D	0.89313 (13)	0.12794 (9)	0.57423 (7)	0.0232 (2)
F5D	0.85612 (13)	0.32209 (9)	0.55567 (6)	0.0211 (2)
F6D	0.78968 (14)	0.21482 (10)	0.46498 (6)	0.0238 (3)
Si1E	0.56253 (6)	0.18625 (4)	0.22561 (3)	0.01778 (12)
F1E	0.71772 (14)	0.06581 (9)	0.20444 (6)	0.0224 (2)
F2E	0.45671 (14)	0.10710 (10)	0.26609 (7)	0.0239 (3)
F3E	0.65991 (14)	0.19000 (9)	0.30210 (6)	0.0215 (2)
F4E	0.41488 (14)	0.30467 (10)	0.24795 (6)	0.0240 (3)
F5E	0.68021 (16)	0.26028 (10)	0.18600 (7)	0.0290 (3)
F6E	0.47386 (17)	0.18042 (11)	0.14878 (7)	0.0338 (3)
O1F	−0.05819 (18)	0.21010 (13)	0.72577 (8)	0.0281 (3)
H1F	−0.1174	0.2165	0.6904	0.034*
C2F	−0.1528 (3)	0.2917 (2)	0.77516 (13)	0.0383 (6)
H2F1	−0.2085	0.3613	0.7499	0.058*
H2F2	−0.0793	0.3066	0.8098	0.058*
H2F3	−0.2359	0.2632	0.7997	0.058*
O3F	0.1189 (3)	0.3171 (2)	0.15212 (11)	0.0542 (6)
H3F	0.2191	0.2785	0.1512	0.065*
C4F	0.0257 (8)	0.3911 (4)	0.0983 (2)	0.0957 (17)
H4F1	0.0258	0.4681	0.1069	0.144*
H4F2	−0.0886	0.3884	0.1000	0.144*
H4F3	0.0768	0.3669	0.0515	0.144*
O5F	0.4231 (5)	0.3749 (2)	0.06952 (15)	0.1084 (13)
H5F	0.3443	0.3593	0.0911	0.130*
C6F	0.4393 (6)	0.4698 (3)	0.0981 (2)	0.0769 (12)
H6F1	0.4004	0.4753	0.1478	0.115*
H6F2	0.3733	0.5354	0.0719	0.115*
H6F3	0.5560	0.4671	0.0952	0.115*

	U11	U22	U33	U12	U13	U23
N1	0.0116 (7)	0.0140 (7)	0.0140 (7)	−0.0053 (5)	0.0001 (5)	0.0006 (5)
C2A	0.0129 (8)	0.0126 (8)	0.0181 (8)	−0.0052 (6)	−0.0003 (6)	0.0011 (6)
C3A	0.0117 (8)	0.0170 (8)	0.0195 (9)	−0.0054 (6)	0.0000 (6)	0.0011 (7)
C4A	0.0116 (8)	0.0163 (8)	0.0204 (9)	−0.0055 (6)	0.0007 (6)	−0.0005 (7)
N5A	0.0135 (7)	0.0151 (7)	0.0182 (8)	−0.0059 (6)	−0.0005 (6)	0.0010 (6)
C6A	0.0147 (8)	0.0148 (8)	0.0220 (9)	−0.0062 (6)	−0.0008 (7)	0.0015 (7)
C7A	0.0173 (8)	0.0154 (8)	0.0211 (9)	−0.0076 (6)	−0.0002 (7)	0.0004 (6)
S8A	0.0173 (3)	0.0193 (3)	0.0252 (4)	−0.0080 (2)	0.0006 (2)	−0.0068 (2)
C9A	0.0147 (11)	0.0185 (11)	0.0296 (12)	−0.0066 (9)	−0.0027 (9)	0.0026 (9)
C10A	0.0169 (10)	0.0216 (11)	0.0279 (12)	−0.0062 (9)	0.0027 (9)	0.0018 (10)
C11A	0.0217 (12)	0.0180 (15)	0.0233 (15)	−0.0061 (10)	0.0001 (11)	−0.0031 (11)
C7A'	0.0173 (8)	0.0154 (8)	0.0211 (9)	−0.0076 (6)	−0.0002 (7)	0.0004 (6)
S8A'	0.0157 (14)	0.0161 (17)	0.029 (2)	−0.0055 (12)	0.0051 (12)	−0.0014 (13)
C9A'	0.016 (3)	0.017 (3)	0.025 (3)	−0.009 (2)	−0.001 (2)	0.002 (3)
C10M	0.014 (2)	0.017 (3)	0.026 (3)	−0.005 (2)	−0.006 (2)	0.002 (2)
C11M	0.017 (2)	0.018 (2)	0.024 (2)	−0.004 (2)	0.000 (2)	−0.001 (2)
C2B	0.0145 (8)	0.0142 (8)	0.0167 (8)	−0.0032 (6)	−0.0018 (6)	0.0026 (6)
C3B	0.0124 (8)	0.0155 (8)	0.0163 (8)	−0.0052 (6)	−0.0016 (6)	0.0021 (6)
C4B	0.0221 (9)	0.0190 (9)	0.0162 (9)	−0.0057 (7)	−0.0029 (7)	0.0013 (7)
N5B	0.0181 (8)	0.0215 (8)	0.0155 (8)	−0.0064 (6)	−0.0020 (6)	0.0023 (6)
C6B	0.0241 (9)	0.0320 (10)	0.0207 (9)	−0.0151 (8)	−0.0031 (7)	0.0019 (8)
C7B	0.0208 (9)	0.0244 (9)	0.0220 (9)	−0.0093 (7)	−0.0038 (7)	−0.0003 (7)
S8B	0.0416 (4)	0.0203 (3)	0.0307 (3)	−0.0069 (2)	−0.0068 (3)	0.0002 (2)
C9B	0.0341 (13)	0.0312 (13)	0.0232 (11)	−0.0109 (10)	−0.0038 (9)	−0.0060 (9)
C10B	0.0233 (11)	0.0305 (12)	0.0213 (10)	−0.0083 (9)	−0.0042 (8)	0.0012 (9)
C11B	0.0261 (13)	0.0284 (13)	0.0284 (13)	−0.0081 (11)	−0.0024 (12)	−0.0008 (11)
C7B'	0.0208 (9)	0.0244 (9)	0.0220 (9)	−0.0093 (7)	−0.0038 (7)	−0.0003 (7)
S8B'	0.027 (3)	0.031 (2)	0.030 (3)	−0.004 (2)	−0.002 (2)	0.007 (2)
C9B'	0.033 (4)	0.033 (4)	0.024 (3)	−0.007 (4)	−0.006 (3)	0.000 (3)
C10N	0.037 (3)	0.028 (3)	0.027 (3)	−0.011 (3)	−0.006 (3)	−0.002 (3)
C11N	0.032 (3)	0.026 (3)	0.026 (3)	−0.009 (3)	−0.005 (3)	0.001 (2)
C2C	0.0168 (8)	0.0152 (8)	0.0147 (8)	−0.0060 (6)	−0.0008 (6)	−0.0010 (6)
C3C	0.0160 (8)	0.0209 (9)	0.0172 (9)	−0.0046 (7)	−0.0013 (7)	−0.0015 (7)
C4C	0.0201 (9)	0.0276 (10)	0.0164 (9)	−0.0064 (8)	−0.0032 (7)	−0.0023 (7)
N5C	0.0180 (8)	0.0329 (10)	0.0173 (8)	−0.0053 (7)	−0.0015 (6)	−0.0040 (7)
C6C	0.0242 (10)	0.0363 (11)	0.0187 (9)	−0.0057 (8)	0.0021 (7)	−0.0080 (8)
C7C	0.0251 (9)	0.0404 (11)	0.0177 (9)	−0.0094 (8)	0.0019 (7)	−0.0081 (8)
S8C	0.0222 (3)	0.0516 (4)	0.0213 (3)	−0.0101 (3)	0.0023 (2)	−0.0001 (3)
C9C	0.0369 (13)	0.0499 (15)	0.0197 (12)	−0.0138 (11)	−0.0029 (10)	0.0025 (12)
C10C	0.0327 (12)	0.0470 (15)	0.0260 (12)	−0.0078 (11)	−0.0044 (10)	−0.0015 (10)
C11C	0.0235 (13)	0.0476 (16)	0.0262 (12)	−0.0089 (14)	0.0037 (11)	−0.0081 (11)
C7C'	0.0251 (9)	0.0404 (11)	0.0177 (9)	−0.0094 (8)	0.0019 (7)	−0.0081 (8)
S8C'	0.040 (3)	0.062 (3)	0.030 (3)	−0.012 (3)	0.000 (2)	−0.002 (2)
C9C'	0.033 (3)	0.048 (3)	0.025 (3)	−0.009 (3)	−0.001 (3)	−0.003 (3)
C10O	0.034 (3)	0.049 (3)	0.024 (3)	−0.011 (3)	−0.001 (3)	−0.002 (3)
C11O	0.032 (2)	0.046 (3)	0.024 (2)	−0.010 (2)	0.001 (2)	−0.004 (2)
Si1D	0.0105 (2)	0.0138 (2)	0.0202 (2)	−0.00363 (17)	−0.00076 (18)	−0.00068 (18)
F1D	0.0143 (5)	0.0182 (5)	0.0197 (5)	−0.0002 (4)	−0.0024 (4)	0.0001 (4)
F2D	0.0134 (5)	0.0209 (6)	0.0354 (7)	−0.0081 (4)	−0.0008 (5)	−0.0018 (5)
F3D	0.0214 (6)	0.0266 (6)	0.0192 (6)	−0.0049 (5)	−0.0018 (4)	0.0019 (4)
F4D	0.0123 (5)	0.0153 (5)	0.0418 (7)	−0.0038 (4)	−0.0034 (5)	0.0032 (5)
F5D	0.0171 (5)	0.0163 (5)	0.0321 (6)	−0.0079 (4)	−0.0047 (5)	0.0016 (4)
F6D	0.0163 (5)	0.0310 (6)	0.0225 (6)	−0.0052 (5)	0.0036 (4)	−0.0076 (5)
Si1E	0.0178 (2)	0.0174 (2)	0.0170 (2)	−0.00358 (19)	−0.00032 (19)	−0.00119 (18)
F1E	0.0222 (6)	0.0178 (5)	0.0247 (6)	−0.0032 (4)	0.0058 (4)	−0.0017 (4)
F2E	0.0188 (5)	0.0229 (6)	0.0315 (6)	−0.0091 (5)	0.0042 (5)	−0.0045 (5)
F3E	0.0189 (5)	0.0216 (6)	0.0232 (6)	−0.0045 (4)	−0.0051 (4)	−0.0025 (4)
F4E	0.0215 (6)	0.0205 (6)	0.0258 (6)	0.0003 (4)	−0.0015 (5)	−0.0035 (5)
F5E	0.0316 (7)	0.0213 (6)	0.0321 (7)	−0.0065 (5)	0.0076 (5)	0.0047 (5)
F6E	0.0382 (7)	0.0352 (7)	0.0234 (6)	−0.0030 (6)	−0.0099 (5)	−0.0060 (5)
O1F	0.0200 (7)	0.0365 (8)	0.0248 (7)	−0.0038 (6)	−0.0038 (6)	−0.0003 (6)
C2F	0.0308 (12)	0.0528 (16)	0.0279 (12)	−0.0077 (11)	0.0009 (9)	−0.0025 (11)
O3F	0.0499 (12)	0.0736 (15)	0.0520 (12)	−0.0392 (11)	0.0187 (10)	−0.0245 (11)
C4F	0.186 (6)	0.068 (3)	0.047 (2)	−0.061 (3)	0.014 (3)	−0.0029 (19)
O5F	0.187 (4)	0.0490 (15)	0.0632 (17)	0.0094 (18)	−0.056 (2)	−0.0066 (13)
C6F	0.121 (4)	0.0403 (18)	0.075 (3)	−0.029 (2)	−0.036 (2)	0.0161 (17)

N1—C2A	1.505 (2)	C9B'—H9B'	0.9500
N1—C2C	1.507 (2)	C10N—C11N	1.418 (4)
N1—C2B	1.509 (2)	C10N—H10N	0.9500
N1—H1	0.90 (2)	C11N—H11N	0.9500
C2A—C3A	1.527 (2)	C2C—C3C	1.522 (3)
C2A—H2A1	0.9900	C2C—H2C1	0.9900
C2A—H2A2	0.9900	C2C—H2C2	0.9900
C3A—C4A	1.519 (2)	C3C—C4C	1.522 (3)
C3A—H3A1	0.9900	C3C—H3C1	0.9900
C3A—H3A2	0.9900	C3C—H3C2	0.9900
C4A—N5A	1.496 (2)	C4C—N5C	1.489 (3)
C4A—H4A1	0.9900	C4C—H4C1	0.9900
C4A—H4A2	0.9900	C4C—H4C2	0.9900
N5A—C6A	1.479 (2)	N5C—C6C	1.510 (2)
N5A—H5A1	0.819 (16)	N5C—H5C1	0.840 (16)
N5A—H5A2	0.829 (16)	N5C—H5C2	0.855 (17)
C6A—C7A'	1.494 (3)	C6C—C7C	1.493 (2)
C6A—C7A	1.497 (2)	C6C—C7C'	1.494 (3)
C6A—H6A1	0.9900	C6C—H6C1	0.9900
C6A—H6A2	0.9900	C6C—H6C2	0.9900
C7A—C11A	1.351 (3)	C7C—C11C	1.343 (3)
C7A—S8A	1.731 (2)	C7C—S8C	1.724 (2)
S8A—C9A	1.715 (2)	S8C—C9C	1.720 (2)
C9A—C10A	1.362 (3)	C9C—C10C	1.364 (3)
C9A—H9A	0.9500	C9C—H9C	0.9500
C10A—C11A	1.420 (3)	C10C—C11C	1.414 (3)
C10A—H10A	0.9500	C10C—H10C	0.9500
C11A—H11A	0.9500	C11C—H11C	0.9500
C7A'—C11M	1.350 (4)	C7C'—C11O	1.348 (4)
C7A'—S8A'	1.725 (4)	C7C'—S8C'	1.726 (4)
S8A'—C9A'	1.716 (4)	S8C'—C9C'	1.716 (4)
C9A'—C10M	1.362 (4)	C9C'—C10O	1.364 (4)
C9A'—H9A'	0.9500	C9C'—H9C'	0.9500
C10M—C11M	1.419 (4)	C10O—C11O	1.420 (4)
C10M—H10M	0.9500	C10O—H10O	0.9500
C11M—H11M	0.9500	C11O—H11O	0.9500
C2B—C3B	1.523 (2)	Si1D—F2D	1.6740 (12)
C2B—H2B1	0.9900	Si1D—F3D	1.6886 (12)
C2B—H2B2	0.9900	Si1D—F5D	1.6908 (12)
C3B—C4B	1.517 (2)	Si1D—F1D	1.6935 (11)
C3B—H3B1	0.9900	Si1D—F4D	1.6954 (12)
C3B—H3B2	0.9900	Si1D—F6D	1.7112 (12)
C4B—N5B	1.500 (2)	Si1E—F4E	1.6698 (12)
C4B—H4B1	0.9900	Si1E—F6E	1.6742 (13)
C4B—H4B2	0.9900	Si1E—F2E	1.6841 (13)
N5B—C6B	1.499 (2)	Si1E—F3E	1.7013 (12)
N5B—H5B1	0.822 (16)	Si1E—F5E	1.7024 (14)
N5B—H5B2	0.835 (16)	Si1E—F1E	1.7120 (12)
C6B—C7B	1.494 (2)	O1F—C2F	1.425 (3)
C6B—C7B'	1.495 (3)	O1F—H1F	0.8401
C6B—H6B1	0.9900	C2F—H2F1	0.9800
C6B—H6B2	0.9900	C2F—H2F2	0.9800
C7B—C11B	1.351 (3)	C2F—H2F3	0.9800
C7B—S8B	1.728 (2)	O3F—C4F	1.450 (5)
S8B—C9B	1.714 (2)	O3F—H3F	0.8399
C9B—C10B	1.362 (3)	C4F—H4F1	0.9800
C9B—H9B	0.9500	C4F—H4F2	0.9800
C10B—C11B	1.422 (3)	C4F—H4F3	0.9800
C10B—H10B	0.9500	O5F—C6F	1.360 (4)
C11B—H11B	0.9500	O5F—H5F	0.8399
C7B'—C11N	1.349 (4)	C6F—H6F1	0.9800
C7B'—S8B'	1.727 (4)	C6F—H6F2	0.9800
S8B'—C9B'	1.715 (4)	C6F—H6F3	0.9800
C9B'—C10N	1.362 (4)
C2A—N1—C2C	113.98 (14)	S8B'—C9B'—H9B'	124.2
C2A—N1—C2B	114.05 (13)	C9B'—C10N—C11N	112.3 (4)
C2C—N1—C2B	107.64 (13)	C9B'—C10N—H10N	123.8
C2A—N1—H1	104.5 (14)	C11N—C10N—H10N	123.8
C2C—N1—H1	109.1 (14)	C7B'—C11N—C10N	113.3 (6)
C2B—N1—H1	107.3 (14)	C7B'—C11N—H11N	123.4
N1—C2A—C3A	112.52 (14)	C10N—C11N—H11N	123.4
N1—C2A—H2A1	109.1	N1—C2C—C3C	114.61 (14)
C3A—C2A—H2A1	109.1	N1—C2C—H2C1	108.6
N1—C2A—H2A2	109.1	C3C—C2C—H2C1	108.6
C3A—C2A—H2A2	109.1	N1—C2C—H2C2	108.6
H2A1—C2A—H2A2	107.8	C3C—C2C—H2C2	108.6
C4A—C3A—C2A	108.76 (14)	H2C1—C2C—H2C2	107.6
C4A—C3A—H3A1	109.9	C2C—C3C—C4C	106.64 (15)
C2A—C3A—H3A1	109.9	C2C—C3C—H3C1	110.4
C4A—C3A—H3A2	109.9	C4C—C3C—H3C1	110.4
C2A—C3A—H3A2	109.9	C2C—C3C—H3C2	110.4
H3A1—C3A—H3A2	108.3	C4C—C3C—H3C2	110.4
N5A—C4A—C3A	110.09 (14)	H3C1—C3C—H3C2	108.6
N5A—C4A—H4A1	109.6	N5C—C4C—C3C	112.26 (16)
C3A—C4A—H4A1	109.6	N5C—C4C—H4C1	109.2
N5A—C4A—H4A2	109.6	C3C—C4C—H4C1	109.2
C3A—C4A—H4A2	109.6	N5C—C4C—H4C2	109.2
H4A1—C4A—H4A2	108.2	C3C—C4C—H4C2	109.2
C6A—N5A—C4A	111.26 (14)	H4C1—C4C—H4C2	107.9
C6A—N5A—H5A1	112.5 (17)	C4C—N5C—C6C	111.14 (16)
C4A—N5A—H5A1	106.1 (17)	C4C—N5C—H5C1	113.4 (18)
C6A—N5A—H5A2	107.9 (16)	C6C—N5C—H5C1	107.3 (18)
C4A—N5A—H5A2	110.5 (16)	C4C—N5C—H5C2	112.8 (18)
H5A1—N5A—H5A2	109 (2)	C6C—N5C—H5C2	106.8 (18)
N5A—C6A—C7A'	117.3 (2)	H5C1—N5C—H5C2	105 (2)
N5A—C6A—C7A	115.30 (11)	C7C—C6C—N5C	111.07 (13)
N5A—C6A—H6A1	108.4	C7C'—C6C—N5C	108.7 (4)
C7A'—C6A—H6A1	108.8	C7C—C6C—H6C1	109.4
C7A—C6A—H6A1	108.4	C7C'—C6C—H6C1	110.8
N5A—C6A—H6A2	108.4	N5C—C6C—H6C1	109.4
C7A'—C6A—H6A2	106.0	C7C—C6C—H6C2	109.4
C7A—C6A—H6A2	108.4	C7C'—C6C—H6C2	110.5
H6A1—C6A—H6A2	107.5	N5C—C6C—H6C2	109.4
C11A—C7A—C6A	128.3 (2)	H6C1—C6C—H6C2	108.0
C11A—C7A—S8A	110.39 (17)	C11C—C7C—C6C	129.1 (2)
C6A—C7A—S8A	121.29 (16)	C11C—C7C—S8C	111.06 (18)
C9A—S8A—C7A	92.13 (11)	C6C—C7C—S8C	119.79 (17)
C10A—C9A—S8A	111.36 (18)	C9C—S8C—C7C	91.74 (12)
C10A—C9A—H9A	124.3	C10C—C9C—S8C	111.17 (19)
S8A—C9A—H9A	124.3	C10C—C9C—H9C	124.4
C9A—C10A—C11A	112.2 (2)	S8C—C9C—H9C	124.4
C9A—C10A—H10A	123.9	C9C—C10C—C11C	112.3 (2)
C11A—C10A—H10A	123.9	C9C—C10C—H10C	123.9
C7A—C11A—C10A	113.9 (3)	C11C—C10C—H10C	123.9
C7A—C11A—H11A	123.1	C7C—C11C—C10C	113.8 (3)
C10A—C11A—H11A	123.1	C7C—C11C—H11C	123.1
C11M—C7A'—C6A	127.8 (5)	C10C—C11C—H11C	123.1
C11M—C7A'—S8A'	111.4 (4)	C11O—C7C'—C6C	128.5 (5)
C6A—C7A'—S8A'	120.8 (4)	C11O—C7C'—S8C'	109.7 (6)
C9A'—S8A'—C7A'	91.5 (4)	C6C—C7C'—S8C'	121.8 (4)
C10M—C9A'—S8A'	111.7 (4)	C9C'—S8C'—C7C'	92.7 (4)
C10M—C9A'—H9A'	124.2	C10O—C9C'—S8C'	111.1 (4)
S8A'—C9A'—H9A'	124.2	C10O—C9C'—H9C'	124.4
C9A'—C10M—C11M	112.3 (4)	S8C'—C9C'—H9C'	124.4
C9A'—C10M—H10M	123.9	C9C'—C10O—C11O	111.7 (4)
C11M—C10M—H10M	123.9	C9C'—C10O—H10O	124.1
C7A'—C11M—C10M	113.1 (5)	C11O—C10O—H10O	124.1
C7A'—C11M—H11M	123.4	C7C'—C11O—C10O	114.8 (6)
C10M—C11M—H11M	123.4	C7C'—C11O—H11O	122.6
N1—C2B—C3B	114.10 (14)	C10O—C11O—H11O	122.6
N1—C2B—H2B1	108.7	F2D—Si1D—F3D	90.44 (6)
C3B—C2B—H2B1	108.7	F2D—Si1D—F5D	179.41 (7)
N1—C2B—H2B2	108.7	F3D—Si1D—F5D	90.13 (6)
C3B—C2B—H2B2	108.7	F2D—Si1D—F1D	90.85 (6)
H2B1—C2B—H2B2	107.6	F3D—Si1D—F1D	91.33 (6)
C4B—C3B—C2B	107.59 (14)	F5D—Si1D—F1D	89.29 (6)
C4B—C3B—H3B1	110.2	F2D—Si1D—F4D	90.83 (6)
C2B—C3B—H3B1	110.2	F3D—Si1D—F4D	90.12 (6)
C4B—C3B—H3B2	110.2	F5D—Si1D—F4D	89.02 (6)
C2B—C3B—H3B2	110.2	F1D—Si1D—F4D	177.77 (6)
H3B1—C3B—H3B2	108.5	F2D—Si1D—F6D	90.55 (6)
N5B—C4B—C3B	112.11 (15)	F3D—Si1D—F6D	178.66 (6)
N5B—C4B—H4B1	109.2	F5D—Si1D—F6D	88.88 (6)
C3B—C4B—H4B1	109.2	F1D—Si1D—F6D	89.55 (6)
N5B—C4B—H4B2	109.2	F4D—Si1D—F6D	88.97 (6)
C3B—C4B—H4B2	109.2	F4E—Si1E—F6E	91.42 (7)
H4B1—C4B—H4B2	107.9	F4E—Si1E—F2E	91.77 (6)
C6B—N5B—C4B	114.69 (15)	F6E—Si1E—F2E	91.28 (7)
C6B—N5B—H5B1	110.1 (17)	F4E—Si1E—F3E	90.40 (6)
C4B—N5B—H5B1	109.3 (17)	F6E—Si1E—F3E	177.79 (7)
C6B—N5B—H5B2	111.0 (17)	F2E—Si1E—F3E	89.90 (6)
C4B—N5B—H5B2	106.5 (17)	F4E—Si1E—F5E	91.14 (6)
H5B1—N5B—H5B2	105 (2)	F6E—Si1E—F5E	90.48 (7)
C7B—C6B—N5B	111.93 (12)	F2E—Si1E—F5E	176.57 (7)
C7B'—C6B—N5B	110.4 (3)	F3E—Si1E—F5E	88.24 (7)
C7B—C6B—H6B1	109.2	F4E—Si1E—F1E	178.29 (7)
C7B'—C6B—H6B1	116.9	F6E—Si1E—F1E	90.17 (7)
N5B—C6B—H6B1	109.2	F2E—Si1E—F1E	88.82 (6)
C7B—C6B—H6B2	109.2	F3E—Si1E—F1E	88.00 (6)
C7B'—C6B—H6B2	102.7	F5E—Si1E—F1E	88.22 (6)
N5B—C6B—H6B2	109.2	C2F—O1F—H1F	105.7
H6B1—C6B—H6B2	107.9	O1F—C2F—H2F1	109.5
C11B—C7B—C6B	128.1 (2)	O1F—C2F—H2F2	109.5
C11B—C7B—S8B	110.71 (19)	H2F1—C2F—H2F2	109.5
C6B—C7B—S8B	121.15 (16)	O1F—C2F—H2F3	109.5
C9B—S8B—C7B	92.08 (10)	H2F1—C2F—H2F3	109.5
C10B—C9B—S8B	111.40 (16)	H2F2—C2F—H2F3	109.5
C10B—C9B—H9B	124.3	C4F—O3F—H3F	129.2
S8B—C9B—H9B	124.3	O3F—C4F—H4F1	109.5
C9B—C10B—C11B	112.3 (2)	O3F—C4F—H4F2	109.5
C9B—C10B—H10B	123.9	H4F1—C4F—H4F2	109.5
C11B—C10B—H10B	123.9	O3F—C4F—H4F3	109.5
C7B—C11B—C10B	113.5 (3)	H4F1—C4F—H4F3	109.5
C7B—C11B—H11B	123.2	H4F2—C4F—H4F3	109.5
C10B—C11B—H11B	123.2	C6F—O5F—H5F	108.3
C11N—C7B'—C6B	127.8 (5)	O5F—C6F—H6F1	109.5
C11N—C7B'—S8B'	111.1 (6)	O5F—C6F—H6F2	109.5
C6B—C7B'—S8B'	121.1 (4)	H6F1—C6F—H6F2	109.5
C9B'—S8B'—C7B'	91.7 (4)	O5F—C6F—H6F3	109.5
C10N—C9B'—S8B'	111.6 (4)	H6F1—C6F—H6F3	109.5
C10N—C9B'—H9B'	124.2	H6F2—C6F—H6F3	109.5
C2C—N1—C2A—C3A	−64.80 (19)	C6B—C7B—C11B—C10B	179.58 (16)
C2B—N1—C2A—C3A	59.36 (19)	S8B—C7B—C11B—C10B	−0.7 (3)
N1—C2A—C3A—C4A	168.83 (14)	C9B—C10B—C11B—C7B	0.4 (3)
C2A—C3A—C4A—N5A	176.53 (14)	N5B—C6B—C7B'—C11N	−103.1 (7)
C3A—C4A—N5A—C6A	160.71 (15)	N5B—C6B—C7B'—S8B'	76.8 (7)
C4A—N5A—C6A—C7A'	171.0 (3)	C11N—C7B'—S8B'—C9B'	−0.1 (2)
C4A—N5A—C6A—C7A	169.09 (16)	C6B—C7B'—S8B'—C9B'	179.93 (12)
N5A—C6A—C7A—C11A	92.3 (2)	C7B'—S8B'—C9B'—C10N	0.1 (3)
N5A—C6A—C7A—S8A	−87.28 (15)	S8B'—C9B'—C10N—C11N	−0.1 (4)
C11A—C7A—S8A—C9A	1.60 (15)	C6B—C7B'—C11N—C10N	−180.0 (2)
C6A—C7A—S8A—C9A	−178.74 (9)	S8B'—C7B'—C11N—C10N	0.1 (3)
C7A—S8A—C9A—C10A	−1.32 (17)	C9B'—C10N—C11N—C7B'	0.0 (5)
S8A—C9A—C10A—C11A	0.7 (3)	C2A—N1—C2C—C3C	−51.9 (2)
C6A—C7A—C11A—C10A	178.88 (14)	C2B—N1—C2C—C3C	−179.49 (15)
S8A—C7A—C11A—C10A	−1.5 (2)	N1—C2C—C3C—C4C	−171.96 (15)
C9A—C10A—C11A—C7A	0.5 (3)	C2C—C3C—C4C—N5C	−171.57 (15)
N5A—C6A—C7A'—C11M	−93.3 (4)	C3C—C4C—N5C—C6C	177.08 (16)
N5A—C6A—C7A'—S8A'	86.7 (3)	C4C—N5C—C6C—C7C	−167.71 (17)
C11M—C7A'—S8A'—C9A'	−0.2 (2)	C4C—N5C—C6C—C7C'	−167.9 (3)
C6A—C7A'—S8A'—C9A'	179.87 (12)	N5C—C6C—C7C—C11C	−80.6 (2)
C7A'—S8A'—C9A'—C10M	0.0 (3)	N5C—C6C—C7C—S8C	99.45 (16)
S8A'—C9A'—C10M—C11M	0.2 (4)	C11C—C7C—S8C—C9C	0.03 (16)
C6A—C7A'—C11M—C10M	−179.75 (19)	C6C—C7C—S8C—C9C	179.97 (9)
S8A'—C7A'—C11M—C10M	0.3 (3)	C7C—S8C—C9C—C10C	0.36 (18)
C9A'—C10M—C11M—C7A'	−0.3 (4)	S8C—C9C—C10C—C11C	−0.7 (3)
C2A—N1—C2B—C3B	48.1 (2)	C6C—C7C—C11C—C10C	179.66 (14)
C2C—N1—C2B—C3B	175.60 (14)	S8C—C7C—C11C—C10C	−0.4 (2)
N1—C2B—C3B—C4B	159.79 (14)	C9C—C10C—C11C—C7C	0.7 (3)
C2B—C3B—C4B—N5B	−177.89 (15)	N5C—C6C—C7C'—C11O	98.2 (6)
C3B—C4B—N5B—C6B	−68.1 (2)	N5C—C6C—C7C'—S8C'	−81.8 (6)
C4B—N5B—C6B—C7B	−165.62 (16)	C11O—C7C'—S8C'—C9C'	0.0 (2)
C4B—N5B—C6B—C7B'	−174.4 (3)	C6C—C7C'—S8C'—C9C'	179.98 (13)
N5B—C6B—C7B—C11B	67.9 (2)	C7C'—S8C'—C9C'—C10O	0.0 (3)
N5B—C6B—C7B—S8B	−111.77 (16)	S8C'—C9C'—C10O—C11O	−0.1 (4)
C11B—C7B—S8B—C9B	0.61 (17)	C6C—C7C'—C11O—C10O	180.0 (2)
C6B—C7B—S8B—C9B	−179.63 (9)	S8C'—C7C'—C11O—C10O	0.0 (3)
C7B—S8B—C9B—C10B	−0.38 (16)	C9C'—C10O—C11O—C7C'	0.1 (5)
S8B—C9B—C10B—C11B	0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···F4Di	0.90 (3)	2.51 (2)	3.171 (2)	131.3 (18)
N1—H1···F5Di	0.90 (3)	2.54 (2)	3.2005 (19)	131.1 (19)
N1—H1···F6Di	0.90 (2)	1.91 (2)	2.7810 (18)	162 (2)
N5A—H5A1···F1D	0.82 (2)	2.02 (2)	2.775 (2)	153 (2)
N5A—H5A1···F6D	0.82 (2)	2.44 (2)	2.985 (2)	125 (2)
N5A—H5A2···F3E	0.83 (2)	1.94 (2)	2.759 (2)	172 (2)
N5A—H5A2···F4E	0.83 (2)	2.63 (2)	3.029 (2)	111 (2)
N5B—H5B1···F1Eii	0.82 (2)	1.92 (2)	2.736 (2)	170 (2)
N5B—H5B1···F2Eii	0.82 (2)	2.47 (2)	2.969 (2)	120 (2)
N5B—H5B2···O1F	0.84 (2)	1.98 (2)	2.790 (2)	163 (2)
N5C—H5C1···F5Ei	0.84 (2)	2.00 (2)	2.828 (2)	171 (3)
N5C—H5C1···F1Ei	0.84 (2)	2.41 (2)	2.932 (2)	121 (2)
N5C—H5C2···O3F	0.86 (2)	1.92 (2)	2.758 (3)	168 (3)
O1F—H1F···F3Di	0.84	1.95	2.7374 (19)	156
O1F—H1F···F4Di	0.84	2.43	3.144 (2)	139
O3F—H3F···F6E	0.84	2.13	2.974 (3)	180
O3F—H3F···F4E	0.84	2.61	3.118 (3)	120
O5F—H5F···O3F	0.84	2.39	3.226 (5)	179

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯F4D i	0.90 (3)	2.51 (2)	3.171 (2)	131.3 (18)
N1—H1⋯F5D i	0.90 (3)	2.54 (2)	3.2005 (19)	131.1 (19)
N1—H1⋯F6D i	0.90 (2)	1.91 (2)	2.7810 (18)	162 (2)
N5A—H5A1⋯F1D	0.82 (2)	2.02 (2)	2.775 (2)	153 (2)
N5A—H5A1⋯F6D	0.82 (2)	2.44 (2)	2.985 (2)	125 (2)
N5A—H5A2⋯F3E	0.83 (2)	1.94 (2)	2.759 (2)	172 (2)
N5A—H5A2⋯F4E	0.83 (2)	2.63 (2)	3.029 (2)	111 (2)
N5B—H5B1⋯F1E ii	0.82 (2)	1.92 (2)	2.736 (2)	170 (2)
N5B—H5B1⋯F2E ii	0.82 (2)	2.47 (2)	2.969 (2)	120 (2)
N5B—H5B2⋯O1F	0.84 (2)	1.98 (2)	2.790 (2)	163 (2)
N5C—H5C1⋯F5E i	0.84 (2)	2.00 (2)	2.828 (2)	171 (3)
N5C—H5C1⋯F1E i	0.84 (2)	2.41 (2)	2.932 (2)	121 (2)
N5C—H5C2⋯O3F	0.86 (2)	1.92 (2)	2.758 (3)	168 (3)
O1F—H1F⋯F3D i	0.84	1.95	2.7374 (19)	156
O1F—H1F⋯F4D i	0.84	2.43	3.144 (2)	139
O3F—H3F⋯F6E	0.84	2.13	2.974 (3)	180
O3F—H3F⋯F4E	0.84	2.61	3.118 (3)	120
O5F—H5F⋯O3F	0.84	2.39	3.226 (5)	179

Symmetry codes: (i) ; (ii) .