N1-(Thio­phen-2-ylmeth­yl)-N3,N3-bis­[3-(thio­phen-2-yl­methyl­ammonio)­prop­yl]propane-1,3-di­ammonium hexa­fluorido­silicate methanol tris­olvate

Haque, S.A.; Cooper, D.N.; Powell, D.R.; Venkatraman, R.; Hossain, M.A.

doi:10.1107/S1600536813029565

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 12| December 2013| Pages o1739-o1740

doi:10.1107/S1600536813029565

Open

access

N¹-(Thiophen-2-ylmethyl)-N³,N³-bis[3-(thiophen-2-ylmethylammonio)propyl]propane-1,3-diammonium hexafluoridosilicate methanol trisolvate

Syed A. Haque,^a Dominique N. Cooper,^a Douglas R. Powell,^b Ramaiyer Venkatraman ^a and Md. Alamgir Hossain ^a ^*

^aDepartment of Chemistry and Biochemistry, Jackson State University, Jackson, MS 39217, USA, and ^bDepartment of Chemistry and Biochemistry, University of Oklahoma, Norman, OK 73019, USA
^*Correspondence e-mail: alamgir.hossain@jsums.edu

(Received 17 October 2013; accepted 27 October 2013; online 6 November 2013)

In the title compound, C₂₄H₄₀N₄S₃⁴⁺·2SiF₆²⁻·3CH₃OH, the central tertiary amine function is protonated and is connected to three thiophen-2-ylmethylamino-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 SiF₆²⁻ anion bonded via two N—H⋯F interactions with the protonated amine group on the middle arm, while two methanol solvent molecules 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 molecules and between the solvent molecules and the anions, respectively, are also observed. All three thiophene 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).

CCDC reference: 968755

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

C₂₄H₄₀N₄S₃⁴⁺·2SiF₆²⁻·3CH₄O
M_r = 861.09
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.044
wR(F²) = 0.125
S = 1.00
9447 reflections
604 parameters
642 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.94 e Å⁻³
Δρ_min = −0.80 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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

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.

Supporting information

CCDC reference: 968755

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813029565/wm2779sup1.cif

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

checkCIF report

Comment top

Polyamine-based synthetic molecules are known as excellent hosts for binding to a variety of anions both in solution and solid state (McKee et al., 2003). Such molecules are particularly useful for selective recognition of environmentally and biologically important polyatomic anions, forming stable host-guest complexes via hydrogen bonding and electrostatic interactions (Hossain, 2008; Mendy et al., 2010). For example, our group recently reported a tripodal host containing ethylene chains in the arms, which provides the complementary of binding sites for a C₃-symmetric nitrate anion (Işıklan et al., 2011). A related tripodal host was found to fully encapsulate a dihydrogen phosphate anion within its cavity (Hossain et al., 2011). In order to obtain the flexible cavity for polyatomic anions, we were interested in synthesizing a tripodal molecule with larger propylene chains. Herein, we report the crystal structure of the title compound, (C₂₄H₄₀N₄S₃)[SiF₆]₂^.3(CH₃OH), that contains two hexafluoridosilicate anions (SiF₆^2-) which originated from the glass container during the crystallization process of the fluoride salt of the ligand. The formation of SiF₆^2- was previously observed by us for a large macrocyclic-based receptor forming a water-fluoride cluster in a molecular box (Hossain et al., 2012).

The cation of the title compound adopts a T-shaped geometry rather than a commonly observed tripodal pocket (Pilate et al., 2010). All four nitrogen atoms in the amine groups are protonated, and the charges are balanced by two dinegatively charged hexafluoridosilicate anions. As shown in Fig. 1, the cationic unit contains two pockets and each pocket is occupied by a single anion bonded to two NH groups with N—H···F bonds in the range of 2.759 (2) to 3.029 (2) Å (Table 1). The single crystal contains three methanol solvent molecules that are also involved in hydrogen bonding interactions. Two methanol molecules (O1 and O3) are held with two side arms, each connecting with a single N—H···O bond. One (O3) of them is interconnected to the third methanol (O5) via one relatively weak O—H···O bond (OH···O = 3.226 (5) Å), and serves also as hydrogen bond donor with two fluoride atoms (F6E and F4E) of a hexafluoridosilicate anion. In the unit cell (Fig. 2), other three nitrogens (N1, N5B and N5C) are also involved in interacting anions via N—H···F bonds (NH···F = 2.758 (3) to 3.2005 (19) Å), each with one SiF₆^2-.

Related literature top

For background to polyamine-based molecules, see: McKee et al. (2003); Hossain (2008); Mendy et al. (2010). For our previous work to 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 top

Tris(3-aminopropyl)amine (0.80 g,4.24 mmol) was dissolved in 50 mL of diethyl ether in a round bottom flask. To this solution, 2-thiophenealdehyde (1.43 g m, 12.7 mmol) dissolved in 50 mL of EtOH was added and left overnight with constant stirring at room temperature. After completion of the reaction, the solvent was evaporated and the product was diluted with methanol (100 mL). Sodium borohydride (2.0 g) was added to the reaction mixture which was stirred overnight at room temperature. After the evaporation of the solvent, the residue was partitioned in water and CH₂Cl₂ (50/50, v/v). The organic layer was collected and dried with anhydrous MgSO₄. The solvent was evaporated under reduced pressure to give an oily product of the free amine. Yield 1.38 g (69%). ¹H NMR (500 MHz, CDCl₃,): δ 7.20 (d, 3H, J = 5.0 ArH), 6.94 (dd, 3H, J=5.5,ArH), δ 6.91 (d, 3H, J = 3.15 ArH), 3.95 (s, 6H, ArCH₂), 2.65 (t, J1 = 6.9 Hz,, 6H, AlphH), 2.44 (t, J1 = 7.1 Hz, 6H, AlphH), 1.82 (broad s, 3H, NH), 1.62 (m, J1 = 7.1 Hz, 6H, AlphH). ¹³C NMR (125 MHz, CDCl₃,): δ 144.19 (Ar-C), 126.52(Ar-C), δ 124.75 (Ar-C), 124.18(Ar-C), 52.24 (Alph-C), 48.47(Alph-C), 47.79 (Alph-C), 27.17 (Alph-C), ESI-MS: m/z (+) 477.8 [M + H]⁺.

The hexafluoride salt was obtained by the dropwise addition of hydrofluoric acid into a glass vial containing free amine (40 mg, 0.08 mmol) in methanol (2 mL) until the pH of the solution became to 2.0. The white precipitate obtained was redissolved in water (1:2, v/v, 1 mL) and the crystals suitable for X-ray analysis were grown after five days from slow evaporation of the solvent at room temperature.

Computing details top

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

Figures top

	Fig. 1. The molecular entities of the title compound, showing the atom-numbering scheme and hydrogen bonding interactions (only the major disordered parts of the thiophene rings are shown). Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The expanded content of the unit cell of the title compound as viewed along the b axis, showing all interacting hexafluoridosilicate anions with the cation and the methanol solvent molecules. Only major hydrogen bonding interactions are shown for clarity. A full list of hydrogen bonds is listed in Table 1.

N¹-(Thiophen-2-ylmethyl)-N³,N³-bis[3-(thiophen-2-ylmethylammonio)propyl]propane-1,3-diammonium hexafluoridosilicate methanol trisolvate top

Crystal data top

C₂₄H₄₀N₄S₃⁴⁺·2SiF₆²⁻·3CH₄O	Z = 2
M_r = 861.09	F(000) = 900
Triclinic, P1	D_x = 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

Data collection top

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

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)] = 0.044	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(F_o²) + (0.070P)² + 1.560P] where P = (F_o² + 2F_c²)/3
9447 reflections	(Δ/σ)_max = 0.006
604 parameters	Δρ_max = 0.94 e Å⁻³
642 restraints	Δρ_min = −0.80 e Å⁻³

Crystal data top

C₂₄H₄₀N₄S₃⁴⁺·2SiF₆²⁻·3CH₄O	γ = 72.206 (3)°
M_r = 861.09	V = 1908.94 (16) Å³
Triclinic, P1	Z = 2
a = 8.4854 (4) Å	Mo Kα radiation
b = 12.5107 (6) Å	µ = 0.35 mm⁻¹
c = 18.9003 (10) Å	T = 100 K
α = 89.024 (2)°	0.58 × 0.16 × 0.03 mm
β = 87.750 (2)°

Data collection top

Bruker APEX CCD diffractometer	9447 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	7815 reflections with I > 2σ(I)
T_min = 0.822, T_max = 0.990	R_int = 0.021
25975 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	642 restraints
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.94 e Å⁻³
9447 reflections	Δρ_min = −0.80 e Å⁻³
604 parameters

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

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

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

Hydrogen-bond geometry (Å, º) top

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	0.819 (16)	2.021 (18)	2.775 (2)	153 (2)
N5A—H5A1···F6D	0.819 (16)	2.44 (2)	2.985 (2)	125 (2)
N5A—H5A2···F3E	0.829 (16)	1.936 (17)	2.759 (2)	172 (2)
N5A—H5A2···F4E	0.829 (16)	2.63 (2)	3.029 (2)	111.2 (18)
N5B—H5B1···F1Eⁱⁱ	0.822 (16)	1.923 (17)	2.736 (2)	170 (2)
N5B—H5B1···F2Eⁱⁱ	0.822 (16)	2.47 (2)	2.969 (2)	120 (2)
N5B—H5B2···O1F	0.835 (16)	1.982 (17)	2.790 (2)	163 (2)
N5C—H5C1···F5Eⁱ	0.840 (16)	1.996 (17)	2.828 (2)	171 (3)
N5C—H5C1···F1Eⁱ	0.840 (16)	2.41 (2)	2.932 (2)	121 (2)
N5C—H5C2···O3F	0.855 (17)	1.916 (18)	2.758 (3)	168 (3)
O1F—H1F···F3Dⁱ	0.84	1.95	2.7374 (19)	155.7
O1F—H1F···F4Dⁱ	0.84	2.43	3.144 (2)	138.9
O3F—H3F···F6E	0.84	2.13	2.974 (3)	180.0
O3F—H3F···F4E	0.84	2.61	3.118 (3)	120.4
O5F—H5F···O3F	0.84	2.39	3.226 (5)	179.4

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

Acknowledgements

The National Science Foundation is acknowledged for a CAREER award (CHE-1056927) to MAH. The NMR core facility at Jackson State University was supported by the National Institutes of Health (G12RR013459). DNC was supported by the National Institutes of Health (NIH)-Minority Access to Research Careers/Undergraduate Student Training in Academic Research (NIH-MARC/U*STAR) Program (Grant No. 5 T34GM007672–34). The authors thank the National Science Foundation (CHE-0130835) and the University of Oklahoma for funds to acquire the diffractometer used in this work.

References

Bruker (2002). SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS, Inc., Madison, Wisconsin, USA. Google Scholar
Hossain, M. A. (2008). Curr. Org. Chem. 12, 1231–1256. Web of Science CrossRef CAS Google Scholar
Hossain, M. A., Işıklan, M., Pramanik, A., Saeed, M. A. & Fronczek, F. R. (2011). Cryst. Growth Des. 12, 567–571. Web of Science CSD CrossRef Google Scholar
Hossain, M. A., Saeed, M. A., Pramanik, A., Wong, B. M., Haque, S. A. & Powell, D. R. (2012). J. Am. Chem. Soc. 134, 11892–11895. Web of Science CSD CrossRef CAS PubMed Google Scholar
Işıklan, M., Saeed, M. A., Pramanik, A., Wong, B. M., Fronczek, F. R. & Hossain, M. A. (2011). Cryst. Growth Des. 11, 959–963. PubMed Google Scholar
McKee, V., Nelson, J. & Town, R. M. (2003). Chem. Soc. Rev., 32, 309–325. Web of Science CrossRef PubMed CAS Google Scholar
Mendy, J. S., Pilate, M. L., Horne, T., Day, V. W. & Hossain, M. A. (2010). Chem. Commun. 46, 6084–6086. Web of Science CSD CrossRef CAS Google Scholar
Pilate, M. L., Blount, H., Fronczek, F. R. & Hossain, M. A. (2010). Acta Cryst. E66, o1833–o1834. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.