supplementary materials


wm2779 scheme

Acta Cryst. (2013). E69, o1739-o1740    [ doi:10.1107/S1600536813029565 ]

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

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

Abstract top

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).

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 (SiF62-) which originated from the glass container during the crystallization process of the fluoride salt of the ligand. The formation of SiF62- 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 SiF62-.

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.

Refinement top

H atoms on C were placed in idealized positions with C—H distances 0.95 - 0.99 Å and thereafter treated as riding. The coordinates of those on N were refined; H atoms of the hydroxy function of methanol were found from difference syntheses and were refined with a distance restraint of 0.84 Å. Uiso for H was assigned as 1.2 times Ueq of the attached atom (1.5 for methyl). A torsional parameter was refined for each methyl group. The largest residual density peak was 1.50 Å from O2.

The constraints and restraints used in refinement were as follows. The geometry of 1-2 and 1-3 distances of non-hydrogen atoms in the three thiophene groups and the adjacent carbons were restrained to be similar with a standard deviation of 0.004 Å for 1-2 distances and 0.006-0.008 Å for 1-3 distances. In addition, these same atoms were restrained to be approximately in a plane within a standard deviation of 0.008 Å. The displacement parameters of these atoms were restrained to conform to a "rigid bond", i.e., the components of the displacement parameters in the directions of bonds were restrained to be equal within a standard deviation of 0.006 Å. The displacement parameters of the disordered atoms were also restrained to be similar if the atoms were within 2.0 Å of other disordered atoms with a standard deviation of 0.006. The atoms C11M, C11N, and C11O were restrained to have approximately isotropic displacement parameters with a standard deviation of 0.006. The bond lengths of the N5-H groups were all restrainted to be about 0.80Å with a standard deviation of 0.02. Finally the displacement parameters of the disordered pairs of the C7 atoms, that were very close to each other, were constrained to be equal.

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
[Figure 1] 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.
[Figure 2] 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+·2SiF62·3CH4OZ = 2
Mr = 861.09F(000) = 900
Triclinic, P1Dx = 1.498 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.4854 (4) ÅCell parameters from 9116 reflections
b = 12.5107 (6) Åθ = 2.5–28.3°
c = 18.9003 (10) ŵ = 0.35 mm1
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 tube7815 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
φ and ω scansθmax = 28.3°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 1111
Tmin = 0.822, Tmax = 0.990k = 1616
25975 measured reflectionsl = 2425
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H 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 parametersΔρmax = 0.94 e Å3
642 restraintsΔρmin = 0.80 e Å3
Crystal data top
C24H40N4S34+·2SiF62·3CH4Oγ = 72.206 (3)°
Mr = 861.09V = 1908.94 (16) Å3
Triclinic, P1Z = 2
a = 8.4854 (4) ÅMo Kα radiation
b = 12.5107 (6) ŵ = 0.35 mm1
c = 18.9003 (10) ÅT = 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)
Tmin = 0.822, Tmax = 0.990Rint = 0.021
25975 measured reflectionsθmax = 28.3°
Refinement top
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.125Δρmax = 0.94 e Å3
S = 1.00Δρmin = 0.80 e Å3
9447 reflectionsAbsolute structure: ?
604 parametersAbsolute structure parameter: ?
642 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N10.13157 (18)0.16663 (12)0.44971 (8)0.0129 (3)
H10.025 (3)0.1828 (19)0.4645 (12)0.015*
C2A0.1602 (2)0.27924 (14)0.44162 (10)0.0143 (3)
H2A10.12930.32050.48680.017*
H2A20.08760.32330.40480.017*
C3A0.3400 (2)0.26928 (15)0.42114 (10)0.0159 (3)
H3A10.41140.23990.46170.019*
H3A20.37900.21660.38110.019*
C4A0.3505 (2)0.38465 (15)0.39995 (10)0.0159 (3)
H4A10.28400.41190.35770.019*
H4A20.30440.43820.43900.019*
N5A0.52685 (19)0.37908 (13)0.38383 (9)0.0153 (3)
H5A10.570 (3)0.376 (2)0.4221 (10)0.018*
H5A20.576 (3)0.3214 (16)0.3613 (11)0.018*
C6A0.53771 (19)0.47655 (14)0.34078 (9)0.0168 (3)
H6A10.46140.54560.36230.020*
H6A20.49850.46970.29290.020*
C7A0.7067 (2)0.49026 (14)0.33317 (11)0.0174 (3)0.828 (3)
S8A0.77713 (7)0.56389 (5)0.39491 (3)0.01999 (19)0.828 (3)
C9A0.9620 (3)0.5433 (2)0.34880 (15)0.0206 (5)0.828 (3)
H9A1.04770.57190.36270.025*0.828 (3)
C10A0.9704 (3)0.4808 (2)0.28972 (15)0.0222 (5)0.828 (3)
H10A1.06360.45980.25760.027*0.828 (3)
C11A0.8239 (4)0.4505 (3)0.28160 (17)0.0210 (7)0.828 (3)
H11A0.80970.40640.24340.025*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'1.08940.47080.26080.022*0.172 (3)
C10M0.9351 (12)0.5504 (11)0.3430 (7)0.0186 (14)0.172 (3)
H10M1.00070.58980.36400.022*0.172 (3)
C11M0.7739 (10)0.5543 (9)0.3684 (5)0.0202 (13)0.172 (3)
H11M0.72010.59650.40850.024*0.172 (3)
C2B0.2348 (2)0.09184 (15)0.50512 (9)0.0154 (3)
H2B10.35070.06340.48660.018*
H2B20.19400.02630.51330.018*
C3B0.2323 (2)0.14949 (15)0.57565 (9)0.0145 (3)
H3B10.30940.19510.57310.017*
H3B20.11950.19960.58740.017*
C4B0.2852 (2)0.05860 (16)0.63168 (10)0.0192 (4)
H4B10.21070.01120.63180.023*
H4B20.39890.01020.61970.023*
N5B0.2812 (2)0.10644 (14)0.70420 (9)0.0183 (3)
H5B10.291 (3)0.0564 (17)0.7339 (11)0.022*
H5B20.186 (2)0.1499 (18)0.7114 (13)0.022*
C6B0.4083 (2)0.16507 (18)0.71464 (9)0.0241 (4)
H6B10.51630.11900.69400.029*
H6B20.37570.23790.68920.029*
C7B0.42679 (18)0.18499 (18)0.79115 (10)0.0218 (4)0.910 (2)
S8B0.36470 (9)0.31908 (5)0.82559 (4)0.03128 (19)0.910 (2)
C9B0.4257 (3)0.27031 (19)0.90860 (11)0.0291 (5)0.910 (2)
H9B0.41610.31690.94870.035*0.910 (2)
C10B0.4896 (3)0.15638 (18)0.90968 (11)0.0249 (5)0.910 (2)
H10B0.53000.11390.95090.030*0.910 (2)
C11B0.4891 (5)0.1083 (3)0.84208 (15)0.0276 (6)0.910 (2)
H11B0.52870.02980.83360.033*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'0.46220.19030.96780.037*0.090 (2)
C10N0.357 (3)0.3066 (11)0.8918 (6)0.0303 (19)0.090 (2)
H10N0.31720.37300.91930.036*0.090 (2)
C11N0.338 (2)0.3031 (9)0.8178 (6)0.0279 (18)0.090 (2)
H11N0.28460.36720.79030.033*0.090 (2)
C2C0.1575 (2)0.10067 (15)0.38197 (9)0.0153 (3)
H2C10.12390.03240.39080.018*
H2C20.27720.07620.36880.018*
C3C0.0627 (2)0.16447 (16)0.31978 (10)0.0182 (4)
H3C10.10740.22590.30440.022*
H3C20.05600.19730.33330.022*
C4C0.0845 (2)0.07987 (17)0.26041 (10)0.0215 (4)
H4C10.20370.03860.25330.026*
H4C20.02650.02470.27440.026*
N5C0.0187 (2)0.13442 (16)0.19252 (9)0.0232 (4)
H5C10.084 (2)0.168 (2)0.1948 (14)0.028*
H5C20.063 (3)0.1843 (19)0.1787 (13)0.028*
C6C0.0497 (3)0.04944 (17)0.13373 (9)0.0272 (4)
H6C10.16600.00040.13440.033*
H6C20.02330.00170.14160.033*
C7C0.0177 (3)0.10602 (15)0.06322 (10)0.0279 (4)0.890 (3)
S8C0.18115 (8)0.11894 (7)0.01032 (3)0.0321 (2)0.890 (3)
C9C0.0503 (3)0.1870 (3)0.05466 (13)0.0354 (6)0.890 (3)
H9C0.08570.21280.09820.042*0.890 (3)
C10C0.1108 (3)0.1990 (3)0.03549 (15)0.0361 (6)0.890 (3)
H10C0.20170.23510.06410.043*0.890 (3)
C11C0.1271 (4)0.1517 (3)0.03181 (16)0.0329 (7)0.890 (3)
H11C0.23080.15210.05290.039*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'0.18740.25590.07720.044*0.110 (3)
C10O0.0513 (18)0.194 (2)0.0437 (8)0.0361 (17)0.110 (3)
H10O0.11220.21530.08150.043*0.110 (3)
C11O0.1238 (15)0.1333 (18)0.0173 (7)0.0342 (16)0.110 (3)
H11O0.23970.11080.02410.041*0.110 (3)
Si1D0.73108 (6)0.23998 (4)0.55231 (3)0.01483 (11)
F1D0.57427 (13)0.35369 (9)0.52832 (6)0.0184 (2)
F2D0.60821 (13)0.15817 (9)0.54819 (7)0.0226 (2)
F3D0.67788 (14)0.26449 (10)0.63891 (6)0.0230 (2)
F4D0.89313 (13)0.12794 (9)0.57423 (7)0.0232 (2)
F5D0.85612 (13)0.32209 (9)0.55567 (6)0.0211 (2)
F6D0.78968 (14)0.21482 (10)0.46498 (6)0.0238 (3)
Si1E0.56253 (6)0.18625 (4)0.22561 (3)0.01778 (12)
F1E0.71772 (14)0.06581 (9)0.20444 (6)0.0224 (2)
F2E0.45671 (14)0.10710 (10)0.26609 (7)0.0239 (3)
F3E0.65991 (14)0.19000 (9)0.30210 (6)0.0215 (2)
F4E0.41488 (14)0.30467 (10)0.24795 (6)0.0240 (3)
F5E0.68021 (16)0.26028 (10)0.18600 (7)0.0290 (3)
F6E0.47386 (17)0.18042 (11)0.14878 (7)0.0338 (3)
O1F0.05819 (18)0.21010 (13)0.72577 (8)0.0281 (3)
H1F0.11740.21650.69040.034*
C2F0.1528 (3)0.2917 (2)0.77516 (13)0.0383 (6)
H2F10.20850.36130.74990.058*
H2F20.07930.30660.80980.058*
H2F30.23590.26320.79970.058*
O3F0.1189 (3)0.3171 (2)0.15212 (11)0.0542 (6)
H3F0.21910.27850.15120.065*
C4F0.0257 (8)0.3911 (4)0.0983 (2)0.0957 (17)
H4F10.02580.46810.10690.144*
H4F20.08860.38840.10000.144*
H4F30.07680.36690.05150.144*
O5F0.4231 (5)0.3749 (2)0.06952 (15)0.1084 (13)
H5F0.34430.35930.09110.130*
C6F0.4393 (6)0.4698 (3)0.0981 (2)0.0769 (12)
H6F10.40040.47530.14780.115*
H6F20.37330.53540.07190.115*
H6F30.55600.46710.09520.115*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0116 (7)0.0140 (7)0.0140 (7)0.0053 (5)0.0001 (5)0.0006 (5)
C2A0.0129 (8)0.0126 (8)0.0181 (8)0.0052 (6)0.0003 (6)0.0011 (6)
C3A0.0117 (8)0.0170 (8)0.0195 (9)0.0054 (6)0.0000 (6)0.0011 (7)
C4A0.0116 (8)0.0163 (8)0.0204 (9)0.0055 (6)0.0007 (6)0.0005 (7)
N5A0.0135 (7)0.0151 (7)0.0182 (8)0.0059 (6)0.0005 (6)0.0010 (6)
C6A0.0147 (8)0.0148 (8)0.0220 (9)0.0062 (6)0.0008 (7)0.0015 (7)
C7A0.0173 (8)0.0154 (8)0.0211 (9)0.0076 (6)0.0002 (7)0.0004 (6)
S8A0.0173 (3)0.0193 (3)0.0252 (4)0.0080 (2)0.0006 (2)0.0068 (2)
C9A0.0147 (11)0.0185 (11)0.0296 (12)0.0066 (9)0.0027 (9)0.0026 (9)
C10A0.0169 (10)0.0216 (11)0.0279 (12)0.0062 (9)0.0027 (9)0.0018 (10)
C11A0.0217 (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)
C10M0.014 (2)0.017 (3)0.026 (3)0.005 (2)0.006 (2)0.002 (2)
C11M0.017 (2)0.018 (2)0.024 (2)0.004 (2)0.000 (2)0.001 (2)
C2B0.0145 (8)0.0142 (8)0.0167 (8)0.0032 (6)0.0018 (6)0.0026 (6)
C3B0.0124 (8)0.0155 (8)0.0163 (8)0.0052 (6)0.0016 (6)0.0021 (6)
C4B0.0221 (9)0.0190 (9)0.0162 (9)0.0057 (7)0.0029 (7)0.0013 (7)
N5B0.0181 (8)0.0215 (8)0.0155 (8)0.0064 (6)0.0020 (6)0.0023 (6)
C6B0.0241 (9)0.0320 (10)0.0207 (9)0.0151 (8)0.0031 (7)0.0019 (8)
C7B0.0208 (9)0.0244 (9)0.0220 (9)0.0093 (7)0.0038 (7)0.0003 (7)
S8B0.0416 (4)0.0203 (3)0.0307 (3)0.0069 (2)0.0068 (3)0.0002 (2)
C9B0.0341 (13)0.0312 (13)0.0232 (11)0.0109 (10)0.0038 (9)0.0060 (9)
C10B0.0233 (11)0.0305 (12)0.0213 (10)0.0083 (9)0.0042 (8)0.0012 (9)
C11B0.0261 (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)
C10N0.037 (3)0.028 (3)0.027 (3)0.011 (3)0.006 (3)0.002 (3)
C11N0.032 (3)0.026 (3)0.026 (3)0.009 (3)0.005 (3)0.001 (2)
C2C0.0168 (8)0.0152 (8)0.0147 (8)0.0060 (6)0.0008 (6)0.0010 (6)
C3C0.0160 (8)0.0209 (9)0.0172 (9)0.0046 (7)0.0013 (7)0.0015 (7)
C4C0.0201 (9)0.0276 (10)0.0164 (9)0.0064 (8)0.0032 (7)0.0023 (7)
N5C0.0180 (8)0.0329 (10)0.0173 (8)0.0053 (7)0.0015 (6)0.0040 (7)
C6C0.0242 (10)0.0363 (11)0.0187 (9)0.0057 (8)0.0021 (7)0.0080 (8)
C7C0.0251 (9)0.0404 (11)0.0177 (9)0.0094 (8)0.0019 (7)0.0081 (8)
S8C0.0222 (3)0.0516 (4)0.0213 (3)0.0101 (3)0.0023 (2)0.0001 (3)
C9C0.0369 (13)0.0499 (15)0.0197 (12)0.0138 (11)0.0029 (10)0.0025 (12)
C10C0.0327 (12)0.0470 (15)0.0260 (12)0.0078 (11)0.0044 (10)0.0015 (10)
C11C0.0235 (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)
C10O0.034 (3)0.049 (3)0.024 (3)0.011 (3)0.001 (3)0.002 (3)
C11O0.032 (2)0.046 (3)0.024 (2)0.010 (2)0.001 (2)0.004 (2)
Si1D0.0105 (2)0.0138 (2)0.0202 (2)0.00363 (17)0.00076 (18)0.00068 (18)
F1D0.0143 (5)0.0182 (5)0.0197 (5)0.0002 (4)0.0024 (4)0.0001 (4)
F2D0.0134 (5)0.0209 (6)0.0354 (7)0.0081 (4)0.0008 (5)0.0018 (5)
F3D0.0214 (6)0.0266 (6)0.0192 (6)0.0049 (5)0.0018 (4)0.0019 (4)
F4D0.0123 (5)0.0153 (5)0.0418 (7)0.0038 (4)0.0034 (5)0.0032 (5)
F5D0.0171 (5)0.0163 (5)0.0321 (6)0.0079 (4)0.0047 (5)0.0016 (4)
F6D0.0163 (5)0.0310 (6)0.0225 (6)0.0052 (5)0.0036 (4)0.0076 (5)
Si1E0.0178 (2)0.0174 (2)0.0170 (2)0.00358 (19)0.00032 (19)0.00119 (18)
F1E0.0222 (6)0.0178 (5)0.0247 (6)0.0032 (4)0.0058 (4)0.0017 (4)
F2E0.0188 (5)0.0229 (6)0.0315 (6)0.0091 (5)0.0042 (5)0.0045 (5)
F3E0.0189 (5)0.0216 (6)0.0232 (6)0.0045 (4)0.0051 (4)0.0025 (4)
F4E0.0215 (6)0.0205 (6)0.0258 (6)0.0003 (4)0.0015 (5)0.0035 (5)
F5E0.0316 (7)0.0213 (6)0.0321 (7)0.0065 (5)0.0076 (5)0.0047 (5)
F6E0.0382 (7)0.0352 (7)0.0234 (6)0.0030 (6)0.0099 (5)0.0060 (5)
O1F0.0200 (7)0.0365 (8)0.0248 (7)0.0038 (6)0.0038 (6)0.0003 (6)
C2F0.0308 (12)0.0528 (16)0.0279 (12)0.0077 (11)0.0009 (9)0.0025 (11)
O3F0.0499 (12)0.0736 (15)0.0520 (12)0.0392 (11)0.0187 (10)0.0245 (11)
C4F0.186 (6)0.068 (3)0.047 (2)0.061 (3)0.014 (3)0.0029 (19)
O5F0.187 (4)0.0490 (15)0.0632 (17)0.0094 (18)0.056 (2)0.0066 (13)
C6F0.121 (4)0.0403 (18)0.075 (3)0.029 (2)0.036 (2)0.0161 (17)
Geometric parameters (Å, º) top
N1—C2A1.505 (2)C9B'—H9B'0.9500
N1—C2C1.507 (2)C10N—C11N1.418 (4)
N1—C2B1.509 (2)C10N—H10N0.9500
N1—H10.90 (2)C11N—H11N0.9500
C2A—C3A1.527 (2)C2C—C3C1.522 (3)
C2A—H2A10.9900C2C—H2C10.9900
C2A—H2A20.9900C2C—H2C20.9900
C3A—C4A1.519 (2)C3C—C4C1.522 (3)
C3A—H3A10.9900C3C—H3C10.9900
C3A—H3A20.9900C3C—H3C20.9900
C4A—N5A1.496 (2)C4C—N5C1.489 (3)
C4A—H4A10.9900C4C—H4C10.9900
C4A—H4A20.9900C4C—H4C20.9900
N5A—C6A1.479 (2)N5C—C6C1.510 (2)
N5A—H5A10.819 (16)N5C—H5C10.840 (16)
N5A—H5A20.829 (16)N5C—H5C20.855 (17)
C6A—C7A'1.494 (3)C6C—C7C1.493 (2)
C6A—C7A1.497 (2)C6C—C7C'1.494 (3)
C6A—H6A10.9900C6C—H6C10.9900
C6A—H6A20.9900C6C—H6C20.9900
C7A—C11A1.351 (3)C7C—C11C1.343 (3)
C7A—S8A1.731 (2)C7C—S8C1.724 (2)
S8A—C9A1.715 (2)S8C—C9C1.720 (2)
C9A—C10A1.362 (3)C9C—C10C1.364 (3)
C9A—H9A0.9500C9C—H9C0.9500
C10A—C11A1.420 (3)C10C—C11C1.414 (3)
C10A—H10A0.9500C10C—H10C0.9500
C11A—H11A0.9500C11C—H11C0.9500
C7A'—C11M1.350 (4)C7C'—C11O1.348 (4)
C7A'—S8A'1.725 (4)C7C'—S8C'1.726 (4)
S8A'—C9A'1.716 (4)S8C'—C9C'1.716 (4)
C9A'—C10M1.362 (4)C9C'—C10O1.364 (4)
C9A'—H9A'0.9500C9C'—H9C'0.9500
C10M—C11M1.419 (4)C10O—C11O1.420 (4)
C10M—H10M0.9500C10O—H10O0.9500
C11M—H11M0.9500C11O—H11O0.9500
C2B—C3B1.523 (2)Si1D—F2D1.6740 (12)
C2B—H2B10.9900Si1D—F3D1.6886 (12)
C2B—H2B20.9900Si1D—F5D1.6908 (12)
C3B—C4B1.517 (2)Si1D—F1D1.6935 (11)
C3B—H3B10.9900Si1D—F4D1.6954 (12)
C3B—H3B20.9900Si1D—F6D1.7112 (12)
C4B—N5B1.500 (2)Si1E—F4E1.6698 (12)
C4B—H4B10.9900Si1E—F6E1.6742 (13)
C4B—H4B20.9900Si1E—F2E1.6841 (13)
N5B—C6B1.499 (2)Si1E—F3E1.7013 (12)
N5B—H5B10.822 (16)Si1E—F5E1.7024 (14)
N5B—H5B20.835 (16)Si1E—F1E1.7120 (12)
C6B—C7B1.494 (2)O1F—C2F1.425 (3)
C6B—C7B'1.495 (3)O1F—H1F0.8401
C6B—H6B10.9900C2F—H2F10.9800
C6B—H6B20.9900C2F—H2F20.9800
C7B—C11B1.351 (3)C2F—H2F30.9800
C7B—S8B1.728 (2)O3F—C4F1.450 (5)
S8B—C9B1.714 (2)O3F—H3F0.8399
C9B—C10B1.362 (3)C4F—H4F10.9800
C9B—H9B0.9500C4F—H4F20.9800
C10B—C11B1.422 (3)C4F—H4F30.9800
C10B—H10B0.9500O5F—C6F1.360 (4)
C11B—H11B0.9500O5F—H5F0.8399
C7B'—C11N1.349 (4)C6F—H6F10.9800
C7B'—S8B'1.727 (4)C6F—H6F20.9800
S8B'—C9B'1.715 (4)C6F—H6F30.9800
C9B'—C10N1.362 (4)
C2A—N1—C2C113.98 (14)S8B'—C9B'—H9B'124.2
C2A—N1—C2B114.05 (13)C9B'—C10N—C11N112.3 (4)
C2C—N1—C2B107.64 (13)C9B'—C10N—H10N123.8
C2A—N1—H1104.5 (14)C11N—C10N—H10N123.8
C2C—N1—H1109.1 (14)C7B'—C11N—C10N113.3 (6)
C2B—N1—H1107.3 (14)C7B'—C11N—H11N123.4
N1—C2A—C3A112.52 (14)C10N—C11N—H11N123.4
N1—C2A—H2A1109.1N1—C2C—C3C114.61 (14)
C3A—C2A—H2A1109.1N1—C2C—H2C1108.6
N1—C2A—H2A2109.1C3C—C2C—H2C1108.6
C3A—C2A—H2A2109.1N1—C2C—H2C2108.6
H2A1—C2A—H2A2107.8C3C—C2C—H2C2108.6
C4A—C3A—C2A108.76 (14)H2C1—C2C—H2C2107.6
C4A—C3A—H3A1109.9C2C—C3C—C4C106.64 (15)
C2A—C3A—H3A1109.9C2C—C3C—H3C1110.4
C4A—C3A—H3A2109.9C4C—C3C—H3C1110.4
C2A—C3A—H3A2109.9C2C—C3C—H3C2110.4
H3A1—C3A—H3A2108.3C4C—C3C—H3C2110.4
N5A—C4A—C3A110.09 (14)H3C1—C3C—H3C2108.6
N5A—C4A—H4A1109.6N5C—C4C—C3C112.26 (16)
C3A—C4A—H4A1109.6N5C—C4C—H4C1109.2
N5A—C4A—H4A2109.6C3C—C4C—H4C1109.2
C3A—C4A—H4A2109.6N5C—C4C—H4C2109.2
H4A1—C4A—H4A2108.2C3C—C4C—H4C2109.2
C6A—N5A—C4A111.26 (14)H4C1—C4C—H4C2107.9
C6A—N5A—H5A1112.5 (17)C4C—N5C—C6C111.14 (16)
C4A—N5A—H5A1106.1 (17)C4C—N5C—H5C1113.4 (18)
C6A—N5A—H5A2107.9 (16)C6C—N5C—H5C1107.3 (18)
C4A—N5A—H5A2110.5 (16)C4C—N5C—H5C2112.8 (18)
H5A1—N5A—H5A2109 (2)C6C—N5C—H5C2106.8 (18)
N5A—C6A—C7A'117.3 (2)H5C1—N5C—H5C2105 (2)
N5A—C6A—C7A115.30 (11)C7C—C6C—N5C111.07 (13)
N5A—C6A—H6A1108.4C7C'—C6C—N5C108.7 (4)
C7A'—C6A—H6A1108.8C7C—C6C—H6C1109.4
C7A—C6A—H6A1108.4C7C'—C6C—H6C1110.8
N5A—C6A—H6A2108.4N5C—C6C—H6C1109.4
C7A'—C6A—H6A2106.0C7C—C6C—H6C2109.4
C7A—C6A—H6A2108.4C7C'—C6C—H6C2110.5
H6A1—C6A—H6A2107.5N5C—C6C—H6C2109.4
C11A—C7A—C6A128.3 (2)H6C1—C6C—H6C2108.0
C11A—C7A—S8A110.39 (17)C11C—C7C—C6C129.1 (2)
C6A—C7A—S8A121.29 (16)C11C—C7C—S8C111.06 (18)
C9A—S8A—C7A92.13 (11)C6C—C7C—S8C119.79 (17)
C10A—C9A—S8A111.36 (18)C9C—S8C—C7C91.74 (12)
C10A—C9A—H9A124.3C10C—C9C—S8C111.17 (19)
S8A—C9A—H9A124.3C10C—C9C—H9C124.4
C9A—C10A—C11A112.2 (2)S8C—C9C—H9C124.4
C9A—C10A—H10A123.9C9C—C10C—C11C112.3 (2)
C11A—C10A—H10A123.9C9C—C10C—H10C123.9
C7A—C11A—C10A113.9 (3)C11C—C10C—H10C123.9
C7A—C11A—H11A123.1C7C—C11C—C10C113.8 (3)
C10A—C11A—H11A123.1C7C—C11C—H11C123.1
C11M—C7A'—C6A127.8 (5)C10C—C11C—H11C123.1
C11M—C7A'—S8A'111.4 (4)C11O—C7C'—C6C128.5 (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'124.2C10O—C9C'—S8C'111.1 (4)
S8A'—C9A'—H9A'124.2C10O—C9C'—H9C'124.4
C9A'—C10M—C11M112.3 (4)S8C'—C9C'—H9C'124.4
C9A'—C10M—H10M123.9C9C'—C10O—C11O111.7 (4)
C11M—C10M—H10M123.9C9C'—C10O—H10O124.1
C7A'—C11M—C10M113.1 (5)C11O—C10O—H10O124.1
C7A'—C11M—H11M123.4C7C'—C11O—C10O114.8 (6)
C10M—C11M—H11M123.4C7C'—C11O—H11O122.6
N1—C2B—C3B114.10 (14)C10O—C11O—H11O122.6
N1—C2B—H2B1108.7F2D—Si1D—F3D90.44 (6)
C3B—C2B—H2B1108.7F2D—Si1D—F5D179.41 (7)
N1—C2B—H2B2108.7F3D—Si1D—F5D90.13 (6)
C3B—C2B—H2B2108.7F2D—Si1D—F1D90.85 (6)
H2B1—C2B—H2B2107.6F3D—Si1D—F1D91.33 (6)
C4B—C3B—C2B107.59 (14)F5D—Si1D—F1D89.29 (6)
C4B—C3B—H3B1110.2F2D—Si1D—F4D90.83 (6)
C2B—C3B—H3B1110.2F3D—Si1D—F4D90.12 (6)
C4B—C3B—H3B2110.2F5D—Si1D—F4D89.02 (6)
C2B—C3B—H3B2110.2F1D—Si1D—F4D177.77 (6)
H3B1—C3B—H3B2108.5F2D—Si1D—F6D90.55 (6)
N5B—C4B—C3B112.11 (15)F3D—Si1D—F6D178.66 (6)
N5B—C4B—H4B1109.2F5D—Si1D—F6D88.88 (6)
C3B—C4B—H4B1109.2F1D—Si1D—F6D89.55 (6)
N5B—C4B—H4B2109.2F4D—Si1D—F6D88.97 (6)
C3B—C4B—H4B2109.2F4E—Si1E—F6E91.42 (7)
H4B1—C4B—H4B2107.9F4E—Si1E—F2E91.77 (6)
C6B—N5B—C4B114.69 (15)F6E—Si1E—F2E91.28 (7)
C6B—N5B—H5B1110.1 (17)F4E—Si1E—F3E90.40 (6)
C4B—N5B—H5B1109.3 (17)F6E—Si1E—F3E177.79 (7)
C6B—N5B—H5B2111.0 (17)F2E—Si1E—F3E89.90 (6)
C4B—N5B—H5B2106.5 (17)F4E—Si1E—F5E91.14 (6)
H5B1—N5B—H5B2105 (2)F6E—Si1E—F5E90.48 (7)
C7B—C6B—N5B111.93 (12)F2E—Si1E—F5E176.57 (7)
C7B'—C6B—N5B110.4 (3)F3E—Si1E—F5E88.24 (7)
C7B—C6B—H6B1109.2F4E—Si1E—F1E178.29 (7)
C7B'—C6B—H6B1116.9F6E—Si1E—F1E90.17 (7)
N5B—C6B—H6B1109.2F2E—Si1E—F1E88.82 (6)
C7B—C6B—H6B2109.2F3E—Si1E—F1E88.00 (6)
C7B'—C6B—H6B2102.7F5E—Si1E—F1E88.22 (6)
N5B—C6B—H6B2109.2C2F—O1F—H1F105.7
H6B1—C6B—H6B2107.9O1F—C2F—H2F1109.5
C11B—C7B—C6B128.1 (2)O1F—C2F—H2F2109.5
C11B—C7B—S8B110.71 (19)H2F1—C2F—H2F2109.5
C6B—C7B—S8B121.15 (16)O1F—C2F—H2F3109.5
C9B—S8B—C7B92.08 (10)H2F1—C2F—H2F3109.5
C10B—C9B—S8B111.40 (16)H2F2—C2F—H2F3109.5
C10B—C9B—H9B124.3C4F—O3F—H3F129.2
S8B—C9B—H9B124.3O3F—C4F—H4F1109.5
C9B—C10B—C11B112.3 (2)O3F—C4F—H4F2109.5
C9B—C10B—H10B123.9H4F1—C4F—H4F2109.5
C11B—C10B—H10B123.9O3F—C4F—H4F3109.5
C7B—C11B—C10B113.5 (3)H4F1—C4F—H4F3109.5
C7B—C11B—H11B123.2H4F2—C4F—H4F3109.5
C10B—C11B—H11B123.2C6F—O5F—H5F108.3
C11N—C7B'—C6B127.8 (5)O5F—C6F—H6F1109.5
C11N—C7B'—S8B'111.1 (6)O5F—C6F—H6F2109.5
C6B—C7B'—S8B'121.1 (4)H6F1—C6F—H6F2109.5
C9B'—S8B'—C7B'91.7 (4)O5F—C6F—H6F3109.5
C10N—C9B'—S8B'111.6 (4)H6F1—C6F—H6F3109.5
C10N—C9B'—H9B'124.2H6F2—C6F—H6F3109.5
C2C—N1—C2A—C3A64.80 (19)C6B—C7B—C11B—C10B179.58 (16)
C2B—N1—C2A—C3A59.36 (19)S8B—C7B—C11B—C10B0.7 (3)
N1—C2A—C3A—C4A168.83 (14)C9B—C10B—C11B—C7B0.4 (3)
C2A—C3A—C4A—N5A176.53 (14)N5B—C6B—C7B'—C11N103.1 (7)
C3A—C4A—N5A—C6A160.71 (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—C7A169.09 (16)C6B—C7B'—S8B'—C9B'179.93 (12)
N5A—C6A—C7A—C11A92.3 (2)C7B'—S8B'—C9B'—C10N0.1 (3)
N5A—C6A—C7A—S8A87.28 (15)S8B'—C9B'—C10N—C11N0.1 (4)
C11A—C7A—S8A—C9A1.60 (15)C6B—C7B'—C11N—C10N180.0 (2)
C6A—C7A—S8A—C9A178.74 (9)S8B'—C7B'—C11N—C10N0.1 (3)
C7A—S8A—C9A—C10A1.32 (17)C9B'—C10N—C11N—C7B'0.0 (5)
S8A—C9A—C10A—C11A0.7 (3)C2A—N1—C2C—C3C51.9 (2)
C6A—C7A—C11A—C10A178.88 (14)C2B—N1—C2C—C3C179.49 (15)
S8A—C7A—C11A—C10A1.5 (2)N1—C2C—C3C—C4C171.96 (15)
C9A—C10A—C11A—C7A0.5 (3)C2C—C3C—C4C—N5C171.57 (15)
N5A—C6A—C7A'—C11M93.3 (4)C3C—C4C—N5C—C6C177.08 (16)
N5A—C6A—C7A'—S8A'86.7 (3)C4C—N5C—C6C—C7C167.71 (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—C11C80.6 (2)
C7A'—S8A'—C9A'—C10M0.0 (3)N5C—C6C—C7C—S8C99.45 (16)
S8A'—C9A'—C10M—C11M0.2 (4)C11C—C7C—S8C—C9C0.03 (16)
C6A—C7A'—C11M—C10M179.75 (19)C6C—C7C—S8C—C9C179.97 (9)
S8A'—C7A'—C11M—C10M0.3 (3)C7C—S8C—C9C—C10C0.36 (18)
C9A'—C10M—C11M—C7A'0.3 (4)S8C—C9C—C10C—C11C0.7 (3)
C2A—N1—C2B—C3B48.1 (2)C6C—C7C—C11C—C10C179.66 (14)
C2C—N1—C2B—C3B175.60 (14)S8C—C7C—C11C—C10C0.4 (2)
N1—C2B—C3B—C4B159.79 (14)C9C—C10C—C11C—C7C0.7 (3)
C2B—C3B—C4B—N5B177.89 (15)N5C—C6C—C7C'—C11O98.2 (6)
C3B—C4B—N5B—C6B68.1 (2)N5C—C6C—C7C'—S8C'81.8 (6)
C4B—N5B—C6B—C7B165.62 (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—C11B67.9 (2)C7C'—S8C'—C9C'—C10O0.0 (3)
N5B—C6B—C7B—S8B111.77 (16)S8C'—C9C'—C10O—C11O0.1 (4)
C11B—C7B—S8B—C9B0.61 (17)C6C—C7C'—C11O—C10O180.0 (2)
C6B—C7B—S8B—C9B179.63 (9)S8C'—C7C'—C11O—C10O0.0 (3)
C7B—S8B—C9B—C10B0.38 (16)C9C'—C10O—C11O—C7C'0.1 (5)
S8B—C9B—C10B—C11B0.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···F4Di0.90 (3)2.51 (2)3.171 (2)131.3 (18)
N1—H1···F5Di0.90 (3)2.54 (2)3.2005 (19)131.1 (19)
N1—H1···F6Di0.90 (2)1.91 (2)2.7810 (18)162 (2)
N5A—H5A1···F1D0.82 (2)2.02 (2)2.775 (2)153 (2)
N5A—H5A1···F6D0.82 (2)2.44 (2)2.985 (2)125 (2)
N5A—H5A2···F3E0.83 (2)1.94 (2)2.759 (2)172 (2)
N5A—H5A2···F4E0.83 (2)2.63 (2)3.029 (2)111 (2)
N5B—H5B1···F1Eii0.82 (2)1.92 (2)2.736 (2)170 (2)
N5B—H5B1···F2Eii0.82 (2)2.47 (2)2.969 (2)120 (2)
N5B—H5B2···O1F0.84 (2)1.98 (2)2.790 (2)163 (2)
N5C—H5C1···F5Ei0.84 (2)2.00 (2)2.828 (2)171 (3)
N5C—H5C1···F1Ei0.84 (2)2.41 (2)2.932 (2)121 (2)
N5C—H5C2···O3F0.86 (2)1.92 (2)2.758 (3)168 (3)
O1F—H1F···F3Di0.841.952.7374 (19)156
O1F—H1F···F4Di0.842.433.144 (2)139
O3F—H3F···F6E0.842.132.974 (3)180
O3F—H3F···F4E0.842.613.118 (3)120
O5F—H5F···O3F0.842.393.226 (5)179
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···F4Di0.90 (3)2.51 (2)3.171 (2)131.3 (18)
N1—H1···F5Di0.90 (3)2.54 (2)3.2005 (19)131.1 (19)
N1—H1···F6Di0.90 (2)1.91 (2)2.7810 (18)162 (2)
N5A—H5A1···F1D0.819 (16)2.021 (18)2.775 (2)153 (2)
N5A—H5A1···F6D0.819 (16)2.44 (2)2.985 (2)125 (2)
N5A—H5A2···F3E0.829 (16)1.936 (17)2.759 (2)172 (2)
N5A—H5A2···F4E0.829 (16)2.63 (2)3.029 (2)111.2 (18)
N5B—H5B1···F1Eii0.822 (16)1.923 (17)2.736 (2)170 (2)
N5B—H5B1···F2Eii0.822 (16)2.47 (2)2.969 (2)120 (2)
N5B—H5B2···O1F0.835 (16)1.982 (17)2.790 (2)163 (2)
N5C—H5C1···F5Ei0.840 (16)1.996 (17)2.828 (2)171 (3)
N5C—H5C1···F1Ei0.840 (16)2.41 (2)2.932 (2)121 (2)
N5C—H5C2···O3F0.855 (17)1.916 (18)2.758 (3)168 (3)
O1F—H1F···F3Di0.841.952.7374 (19)155.7
O1F—H1F···F4Di0.842.433.144 (2)138.9
O3F—H3F···F6E0.842.132.974 (3)180.0
O3F—H3F···F4E0.842.613.118 (3)120.4
O5F—H5F···O3F0.842.393.226 (5)179.4
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z+1.
Acknowledgements top

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
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