Sodium tris­(glycinium) bis­(hexa­fluoro­silicate) glycine trisolvate

The title compound, Na⁺·3C₂H₆NO₂⁺·2SiF₆^2-·3C₂H₅NO₂, arose from an unexpected reaction of glycine and HF with the glass container. It is an unusual hybrid organic-inorganic network built up from chains of vertex-sharing NaF₄O₂ and SiF₆ octa­hedra. A pair of glycinium/glycine mol­ecules bridges the chains into a sheet via a centrosymmetric O...H...O link. The other organic species inter­act with the network by an extensive N-H...F hydrogen-bond network, including bifurcated and trifurcated bonds. Finally, an extremely short C-H...O inter­action (H...O = 2.25 Å) is seen in the crystal structure. The Na atom has site symmetry .

S1. Comment

The title compound, (I), Na(SiF₆)₂(C₂H₆NO₂)₃(C₂H₅NO₂)₃, arose as an unexpected product during our studies of amino acid fluorides as possible non-linear optical materials. The Na and Si were presumably incorporated from the walls of the glass reaction vessel, mediated by reaction with hydrofluoric acid.

The structure of (I) (Fig. 1) is built up from trans-NaF₄O₂ octahedra (Na site symmetry 1) and SiF₆ octahedra, sharing corners via atoms F4 and F6. The geometries of the Na and Si atoms (Table 1) may be regarded as normal (Allen et al., 1995). Considered by themselves, they form chains propagating in [100] with each Na octahedron linked to its neighbour by two Si polyhedra via F atoms, with notably large Na—F—Si bond angles greater than 164°. The square formed by atoms Na1, Si1, Na1ⁱ and Si1ⁱ [symmetry code: (i) 1 - x, -y, -z] is constrained to be exactly flat by symmetry and the Na···Si1···Na1ⁱ [90.58 (3)°] and Si1···Na1···Si1ⁱ [89.42 (3)°] angles barely deviate from 90°. The NaF₄O₂ polyhedron is a rare one, with only two other examples recorded in Version 5.27 of the Cambridge Structural Database (Allen, 2002), in structures otherwise unrelated to (I).

There are three organic molecules in the asymmetric unit of (I). The C1 species is a well defined C₂H₆NO₂⁺ glycinium cation with C1—O2 [1.3018 (14) Å] much longer than C1—O1 [1.2175 (14) Å], indicating localized single and double bonds, respectively. The positive charge of the cation is localized on the N atom.

The C2 spcies is a neutral C₂H₅NO₂ glycine molecule in its normal (Marsh, 1958) zwitterionic form (i.e. nominal H-atomtransfer from O3 or O4 to N2). Consequently, the C3—O3 and C3—O4 bond lengths [1.2759 (14) and 1.2354 (14) Å, respectively] approach each other, implying a degree of delocalization. The C1 and C3 molecules are linked by an O2—H4···O3 hydrogen bond (Table 2) and it is possible that C3—O3 is lengthened relative to C3—O4 because atom O3 accepts this short strong bond, with O···O = 2.4495 (12) Å.

The C5 molecule sits close to an inversion centre, resulting in an O6···O6ⁱⁱ contact of 2.4312 (16) Å [symmetry code: (ii) -x, 1 - y, -z], whereas atom O5 makes a bond to an adjacent Na⁺ cation [C5—O5 = 1.2366 (14) and C5—O6 = 1.2796 (14) Å]. In order to achieve overall change balance in the structure and to justify the very short O···O contact, we have assumed a symmetrical (single potential well) hydrogen bond (Ichikawa, 1978), with atom H11 located on the inversion centre mid-way between the two crystallorgaphically equivalent O6 atoms. This is strongly supported by our refinements of the structure in space group P1, which resulted in a significant difference peak almost mid-way between the two non-equivalent O atoms in the non-centrosymmetric model. Even so, in the centrosymmetric model, when U_iso(H11) was allowed to refine freely, a value of 0.062 (9) Ų resulted, significantly higher than those of the other H atoms, perhaps suggesting disorder.

Thus, based on the present data, a situation of disordered asymmetric O—H···O and O···H—O bonds (double potential well) cannot be completely ruled out, as they are known to be hard to distinguish from X-ray data alone and indeed may be temperature dependent (Wilson, 2001). Either way, this ensemble in (I) has a formula of C₄H₁₁N₂O₄, i.e. equivalent to one glycinium cation and one glycine molecule (C₂H₆NO₂⁺ + C₂H₅NO₂). These glycinium/glycine pairs serve to bridge the [100] inorganic chains into (001) sheets (Fig. 2). For all three organic molecules, the N atom of the –NH₃ group and one of the O atoms of the –CO₂ group are close to being eclipsed (Table 1), which is not an uncommon conformation for glycine (Natarajan & Zangrando, 1992). The co-existence of glycine molecules and glycinium cations in the same structure is also very common (Nemec et al., 1998).

A large number of N—H···F hydrogen bonds (Table 2) help to consolidate the crystal packing of (I). It is notable that some of these are bifurcated N—H···(F,F) bonds and some are trifurcated N—H···(F,F,F) links. Finally, an exceptionally short C6–H6A···O2(x - 1, y z) interaction (Taylor & Kennard, 1982) with H···O = 2.25 Å occurs in the structure of (I), although its role in the complex crystal packing is not clear.

Together, these interactions generate a structure in which the (001) hybrid sheets sandwich the C1 and C2 organic molecules, with a dense mesh of N—H···F hydrogen bonds linking the two together (Fig. 3).

Related literature

For related literature, see: Allen (2002); Allen et al. (1995); Ichikawa (1978); Marsh (1958); Natarajan & Zangrando (1992); Nemec et al. (1998); Taylor & Kennard (1982); Wilson (2001).

S2. Experimental

An aqueous solution of glycine was mixed with excess 2 N hydrofluoric acid. This solution was allowed to undergo evaporation by heating at 313 K. The resulting solid was dried and purified by repeated crystallization in water. The experiment was conducted in glass vessels. An aqueous saturated solution of the compound synthesized as described above was prepared in water at 323 K. The solution was filtered and kept to undergo slow evaporation by cooling at a rate of 0.5 K per day. A portion of the mother solution was poured into a Petri dish and allowed to undergo evaporation at room temperature. The nucleation time was very long, but optically good tiny crystals of (I) were seen in the Petri dish after about one month. These crystals were used as seeds and suspended in the supersaturated mother solution when the temperature reached 313 K. The growth temperature was maintained at 313 K and large crystals of (I) of dimensions 10 × 6 × 3 mm were harvested after a week.

S3. Refinement

O-bound H atoms were located in difference maps and their positions were freely refined, with U_iso(H) = 1.2U_eq(O). The other H atoms were positioned geometrically, with C—H = 0.99 Å and N—H = 0.91 Å, and refined as riding atoms, with U_iso(H) = 1.2U_eq(C,N). The –NH₃ groups were allowed to rotate but not to tip, to best fit the electron density.

Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK, DENZO (Otwinowski & Minor, 1997) and SORTAV (Blessing, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The asymmetric unit of (I), with the atom-numbering scheme, expanded to show the Na coordination sphere and the organic molecules linked by the O···H···O bond. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as spheres of arbitrary radii. Hydrogen bonds are shown as double dashed lines or open bonds. [Please check added text] [Symmetry codes: (i) -x, -y, -z; (ii) -x, 1 - y, -z; (iii) 1 - x, -y, -z; (iv) x - 1, y, z.]
	Fig. 2. Part of the composite inorganic/organic (001) sheet structure in (I), with the inorganic species shown as polyhedra. The NaF2O4 and SiF6 octahedra are light and dark, respectively. The symmetric O6···H···O6^i link is indicated. C-bound H atoms have been omitted for clarity. [Symmetry codes: (i) -x, 1 - y, -z; (ii) x - 1, y, z.]
	Fig. 3. The unit-cell packing for (I), viewed down [100], with drawing conventions as in Fig. 2.

Sodium tris(glycinium) bis(hexafluorosilicate) tris(glycine)

Crystal data

Na^+·3C2H6NO2^+·2SiF6^2^−·3C2H5NO2	Z = 1
Mr = 760.61	F(000) = 390
Triclinic, P1	Dx = 1.901 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.5364 (1) Å	Cell parameters from 2981 reflections
b = 10.9918 (2) Å	θ = 1.0–27.5°
c = 11.8432 (2) Å	µ = 0.30 mm^−1
α = 107.631 (1)°	T = 120 K
β = 102.397 (1)°	Block, colourless
γ = 93.562 (1)°	0.50 × 0.50 × 0.35 mm
V = 664.56 (2) Å^3

Data collection

Nonius KappaCCD area-detector diffractometer	3041 independent reflections
Radiation source: fine-focus sealed tube	2825 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
ω and ϕ scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −7→7
Tmin = 0.863, Tmax = 0.901	k = −14→14
14359 measured reflections	l = −15→15

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difmap and geom
R[F^2 > 2σ(F^2)] = 0.024	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.061	w = 1/[σ^2(Fo^2) + (0.0238P)^2 + 0.3675P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.002
3041 reflections	Δρmax = 0.39 e Å^−3
212 parameters	Δρmin = −0.37 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.043 (3)

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Na1	0.0000	0.0000	0.0000	0.00863 (14)
Si1	0.38756 (5)	−0.03209 (3)	−0.24502 (3)	0.00795 (9)
F1	0.11609 (12)	−0.03242 (7)	−0.34021 (6)	0.01558 (16)
F2	0.52573 (12)	−0.06514 (6)	−0.36273 (6)	0.01299 (15)
F3	0.31163 (12)	−0.19241 (6)	−0.27208 (6)	0.01305 (15)
F4	0.65857 (13)	−0.03931 (7)	−0.14995 (6)	0.01677 (16)
F5	0.47129 (13)	0.12586 (6)	−0.21366 (6)	0.01395 (15)
F6	0.25299 (14)	0.00102 (7)	−0.12556 (6)	0.01775 (16)
C1	0.8232 (2)	0.71694 (11)	0.32627 (10)	0.0132 (2)
C2	1.0438 (2)	0.76669 (11)	0.28781 (10)	0.0124 (2)
H2A	1.1231	0.6936	0.2460	0.015*
H2B	0.9865	0.8141	0.2302	0.015*
N1	1.22650 (18)	0.85362 (9)	0.39816 (9)	0.0135 (2)
H1	1.3098	0.9147	0.3778	0.016*
H2	1.3372	0.8070	0.4290	0.016*
H3	1.1446	0.8925	0.4554	0.016*
O1	0.78169 (16)	0.77272 (8)	0.42448 (7)	0.01554 (18)
O2	0.69211 (18)	0.61321 (8)	0.24422 (8)	0.0194 (2)
H4	0.569 (3)	0.5640 (16)	0.2747 (15)	0.023*
C3	0.2957 (2)	0.50517 (11)	0.38101 (10)	0.0114 (2)
C4	0.1459 (2)	0.39720 (11)	0.40237 (11)	0.0128 (2)
H4A	0.1703	0.4145	0.4914	0.015*
H4B	−0.0338	0.3958	0.3670	0.015*
N2	0.21964 (18)	0.26954 (9)	0.34721 (9)	0.01177 (19)
H5	0.1301	0.2082	0.3645	0.014*
H6	0.3853	0.2708	0.3784	0.014*
H7	0.1888	0.2511	0.2648	0.014*
O3	0.40409 (17)	0.47046 (8)	0.29384 (8)	0.01905 (19)
O4	0.29796 (16)	0.61620 (8)	0.44798 (8)	0.01640 (18)
C5	−0.0559 (2)	0.32435 (11)	0.03744 (10)	0.0103 (2)
C6	−0.3257 (2)	0.34673 (11)	0.02840 (10)	0.0111 (2)
H6A	−0.3332	0.4303	0.0892	0.013*
H6B	−0.4014	0.3505	−0.0540	0.013*
N3	−0.46791 (17)	0.24179 (9)	0.05096 (9)	0.0120 (2)
H8	−0.6220	0.2626	0.0575	0.014*
H9	−0.3853	0.2307	0.1216	0.014*
H10	−0.4839	0.1675	−0.0123	0.014*
O5	0.01814 (15)	0.23100 (8)	0.06531 (8)	0.01313 (17)
O6	0.08726 (15)	0.40592 (8)	0.01570 (8)	0.01578 (18)
H11	0.0000	0.5000	0.0000	0.019*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Na1	0.0075 (3)	0.0098 (3)	0.0088 (3)	0.0008 (2)	0.0021 (2)	0.0033 (2)
Si1	0.00734 (15)	0.00913 (15)	0.00725 (15)	0.00048 (11)	0.00165 (11)	0.00271 (11)
F1	0.0102 (3)	0.0158 (3)	0.0183 (3)	0.0027 (3)	−0.0019 (3)	0.0055 (3)
F2	0.0160 (3)	0.0137 (3)	0.0112 (3)	0.0029 (3)	0.0072 (3)	0.0040 (3)
F3	0.0141 (3)	0.0098 (3)	0.0150 (3)	−0.0002 (2)	0.0025 (3)	0.0048 (3)
F4	0.0110 (3)	0.0227 (4)	0.0155 (3)	−0.0006 (3)	−0.0032 (3)	0.0095 (3)
F5	0.0171 (3)	0.0097 (3)	0.0140 (3)	−0.0008 (3)	0.0049 (3)	0.0022 (3)
F6	0.0207 (4)	0.0185 (4)	0.0156 (3)	−0.0001 (3)	0.0121 (3)	0.0029 (3)
C1	0.0184 (6)	0.0107 (5)	0.0121 (5)	0.0022 (4)	0.0040 (4)	0.0058 (4)
C2	0.0156 (5)	0.0120 (5)	0.0096 (5)	0.0010 (4)	0.0033 (4)	0.0033 (4)
N1	0.0148 (5)	0.0132 (5)	0.0123 (5)	0.0011 (4)	0.0027 (4)	0.0045 (4)
O1	0.0203 (4)	0.0149 (4)	0.0111 (4)	−0.0009 (3)	0.0058 (3)	0.0031 (3)
O2	0.0278 (5)	0.0136 (4)	0.0139 (4)	−0.0070 (4)	0.0085 (4)	−0.0001 (3)
C3	0.0097 (5)	0.0124 (5)	0.0119 (5)	0.0009 (4)	−0.0001 (4)	0.0057 (4)
C4	0.0141 (5)	0.0093 (5)	0.0164 (5)	0.0023 (4)	0.0069 (4)	0.0039 (4)
N2	0.0121 (4)	0.0105 (5)	0.0139 (5)	0.0023 (3)	0.0048 (4)	0.0044 (4)
O3	0.0266 (5)	0.0149 (4)	0.0156 (4)	−0.0044 (3)	0.0103 (4)	0.0028 (3)
O4	0.0179 (4)	0.0103 (4)	0.0216 (4)	0.0019 (3)	0.0066 (3)	0.0047 (3)
C5	0.0112 (5)	0.0101 (5)	0.0085 (5)	0.0008 (4)	0.0020 (4)	0.0019 (4)
C6	0.0106 (5)	0.0105 (5)	0.0132 (5)	0.0020 (4)	0.0034 (4)	0.0050 (4)
N3	0.0091 (4)	0.0137 (5)	0.0137 (5)	0.0006 (4)	0.0028 (3)	0.0054 (4)
O5	0.0114 (4)	0.0102 (4)	0.0193 (4)	0.0030 (3)	0.0037 (3)	0.0068 (3)
O6	0.0126 (4)	0.0159 (4)	0.0230 (4)	0.0011 (3)	0.0055 (3)	0.0118 (3)

Geometric parameters (Å, º)

Na1—F4^i	2.2150 (6)	O2—H4	1.031 (17)
Na1—F4^ii	2.2150 (6)	C3—O4	1.2353 (14)
Na1—F6^iii	2.2529 (7)	C3—O3	1.2759 (14)
Na1—F6	2.2529 (7)	C3—C4	1.5197 (15)
Na1—O5^iii	2.4085 (8)	C4—N2	1.4809 (14)
Na1—O5	2.4085 (8)	C4—H4A	0.9900
Si1—F1	1.6730 (7)	C4—H4B	0.9900
Si1—F5	1.6741 (7)	N2—H5	0.9100
Si1—F2	1.6871 (7)	N2—H6	0.9100
Si1—F6	1.6922 (7)	N2—H7	0.9100
Si1—F4	1.6938 (7)	O3—H4	1.435 (17)
Si1—F3	1.7008 (7)	C5—O5	1.2365 (14)
F4—Na1^i	2.2150 (6)	C5—O6	1.2797 (14)
C1—O1	1.2175 (14)	C5—C6	1.5152 (15)
C1—O2	1.3017 (14)	C6—N3	1.4786 (14)
C1—C2	1.5179 (16)	C6—H6A	0.9900
C2—N1	1.4833 (14)	C6—H6B	0.9900
C2—H2A	0.9900	N3—H8	0.9100
C2—H2B	0.9900	N3—H9	0.9100
N1—H1	0.9100	N3—H10	0.9100
N1—H2	0.9100	O6—H11	1.22
N1—H3	0.9100
F4^i—Na1—F4^ii	180.0	C2—N1—H1	109.5
F4^i—Na1—F6^iii	92.65 (3)	C2—N1—H2	109.5
F4^ii—Na1—F6^iii	87.35 (3)	H1—N1—H2	109.5
F4^i—Na1—F6	87.35 (3)	C2—N1—H3	109.5
F4^ii—Na1—F6	92.65 (3)	H1—N1—H3	109.5
F6^iii—Na1—F6	180.0	H2—N1—H3	109.5
F4^i—Na1—O5^iii	95.82 (3)	C1—O2—H4	115.0 (9)
F4^ii—Na1—O5^iii	84.18 (3)	O4—C3—O3	126.98 (11)
F6^iii—Na1—O5^iii	92.76 (3)	O4—C3—C4	117.35 (10)
F6—Na1—O5^iii	87.24 (3)	O3—C3—C4	115.66 (10)
F4^i—Na1—O5	84.18 (3)	N2—C4—C3	112.29 (9)
F4^ii—Na1—O5	95.82 (3)	N2—C4—H4A	109.1
F6^iii—Na1—O5	87.24 (3)	C3—C4—H4A	109.1
F6—Na1—O5	92.76 (3)	N2—C4—H4B	109.1
O5^iii—Na1—O5	180.0	C3—C4—H4B	109.1
F1—Si1—F5	92.75 (4)	H4A—C4—H4B	107.9
F1—Si1—F2	90.01 (4)	C4—N2—H5	109.5
F5—Si1—F2	90.28 (3)	C4—N2—H6	109.5
F1—Si1—F6	90.82 (4)	H5—N2—H6	109.5
F5—Si1—F6	89.69 (4)	C4—N2—H7	109.5
F2—Si1—F6	179.16 (4)	H5—N2—H7	109.5
F1—Si1—F4	177.28 (4)	H6—N2—H7	109.5
F5—Si1—F4	89.97 (4)	C3—O3—H4	119.5 (7)
F2—Si1—F4	90.02 (4)	O5—C5—O6	122.74 (10)
F6—Si1—F4	89.14 (4)	O5—C5—C6	120.26 (10)
F1—Si1—F3	89.44 (3)	O6—C5—C6	117.01 (10)
F5—Si1—F3	177.75 (4)	N3—C6—C5	110.35 (9)
F2—Si1—F3	90.26 (3)	N3—C6—H6A	109.6
F6—Si1—F3	89.74 (4)	C5—C6—H6A	109.6
F4—Si1—F3	87.84 (4)	N3—C6—H6B	109.6
Si1—F4—Na1^i	165.79 (5)	C5—C6—H6B	109.6
Si1—F6—Na1	164.78 (4)	H6A—C6—H6B	108.1
O1—C1—O2	126.18 (11)	C6—N3—H8	109.5
O1—C1—C2	120.92 (10)	C6—N3—H9	109.5
O2—C1—C2	112.90 (10)	H8—N3—H9	109.5
N1—C2—C1	108.84 (9)	C6—N3—H10	109.5
N1—C2—H2A	109.9	H8—N3—H10	109.5
C1—C2—H2A	109.9	H9—N3—H10	109.5
N1—C2—H2B	109.9	C5—O5—Na1	145.55 (7)
C1—C2—H2B	109.9	C5—O6—H11	117
H2A—C2—H2B	108.3
F5—Si1—F4—Na1^i	33.61 (17)	O1—C1—C2—N1	19.66 (15)
F2—Si1—F4—Na1^i	123.89 (17)	O2—C1—C2—N1	−160.74 (10)
F6—Si1—F4—Na1^i	−56.08 (17)	O4—C3—C4—N2	−161.49 (10)
F3—Si1—F4—Na1^i	−145.85 (17)	O3—C3—C4—N2	19.24 (14)
F1—Si1—F6—Na1	51.34 (17)	O5—C5—C6—N3	−2.66 (14)
F5—Si1—F6—Na1	144.08 (17)	O6—C5—C6—N3	177.66 (9)
F4—Si1—F6—Na1	−125.94 (17)	O6—C5—O5—Na1	−110.52 (13)
F3—Si1—F6—Na1	−38.10 (17)	C6—C5—O5—Na1	69.82 (17)
F4^i—Na1—F6—Si1	138.38 (17)	F4^i—Na1—O5—C5	163.02 (13)
F4^ii—Na1—F6—Si1	−41.62 (17)	F4^ii—Na1—O5—C5	−16.98 (13)
O5^iii—Na1—F6—Si1	42.42 (17)	F6^iii—Na1—O5—C5	−104.03 (13)
O5—Na1—F6—Si1	−137.58 (17)	F6—Na1—O5—C5	75.97 (13)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···F2^iv	0.91	1.91	2.8115 (12)	169
N1—H1···F5^iv	0.91	2.45	3.0735 (12)	126
N1—H2···O4^v	0.91	2.18	2.8769 (13)	133
N1—H2···O1^v	0.91	2.52	3.2299 (13)	135
N1—H3···F1^vi	0.91	2.35	3.1782 (12)	151
O2—H4···O3	1.031 (17)	1.435 (17)	2.4495 (12)	166.7 (16)
N2—H5···F1^iii	0.91	2.20	3.0750 (12)	161
N2—H5···O1^vii	0.91	2.38	2.8803 (13)	115
N2—H5···F3^iii	0.91	2.43	2.8760 (12)	111
N2—H6···F2^i	0.91	2.30	2.7571 (12)	110
N2—H6···O4^vii	0.91	2.34	3.0904 (13)	140
N2—H6···F3^i	0.91	2.36	3.0088 (12)	128
N2—H7···O5	0.91	2.28	3.1710 (13)	165
N2—H7···F4^i	0.91	2.61	3.1022 (12)	115
N3—H8···O5^ii	0.91	2.03	2.8840 (12)	156
N3—H8···O6^ii	0.91	2.40	3.1720 (13)	143
N3—H9···F3^iii	0.91	1.92	2.8014 (12)	163
N3—H10···F6^ii	0.91	2.15	2.9180 (12)	142
N3—H10···F5^ii	0.91	2.24	2.9383 (12)	133
O6—H11···O6^viii	1.22	1.22	2.4309 (16)	180
C6—H6A···O2^ii	0.99	2.25	3.2316 (14)	172

Symmetry codes: (i) −x+1, −y, −z; (ii) x−1, y, z; (iii) −x, −y, −z; (iv) −x+2, −y+1, −z; (v) x+1, y, z; (vi) x+1, y+1, z+1; (vii) −x+1, −y+1, −z+1; (viii) −x, −y+1, −z.