Hydro­nium bis­(tri­fluoro­methane­sulfon­yl)amide–18-crown-6 (1/1)

The structure of the title compound, H₃O⁺·C₂F₆NO₄S₂⁻·C₁₂H₂₄O₆ or [H₃O⁺·C₁₂H₂₄O₆][N(SO₂CF₃)₂⁻], which is an ionic liquid with a melting point of 341–343 K, has been determined at 113 K. The asymmetric unit consists of two crystallographically independent 18-crown-6 mol­ecules, two hydro­nium ions and two bis­(tri­fluoro­methane­sulfon­yl)amide anions; each 18-crown-6 mol­ecule complexes with a hydro­nium ion. In one 18-crown-6 mol­ecule, a part of the ring exhibits conformational disorder over two sets of sites with an occupancy ratio of 0.533 (13):0.467 (13). One hydro­nium ion is complexed with the ordered 18-crown-6 mol­ecule via O—H...O hydrogen bonds with H₂OH...OC distances of 1.90 (6)–2.19 (7) Å, and the other hydro­nium ion with the disordered crown mol­ecule with distances of 1.85 (6)–2.36 (6) Å. The hydro­nium ions are also linked to the anions via O—H...F hydrogen bonds. The crystal studied was found to be a racemic twin with a component ratio of 0.55 (13):0.45 (13).

Key indicators

• Single-crystal X-ray study
• T = 113 K
• Mean [sigma](C-C) = 0.014 Å
• Disorder in main residue
• R factor = 0.062
• wR factor = 0.162
• Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level B
PLAT340_ALERT_3_B Low Bond Precision on  C-C Bonds ...............     0.0142 Ang.

Author Response: Large s.u.'s of C-C bonds are due to the disorder of 18-crown-6.

Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.450
           From the CIF: _refine_ls_abs_structure_Flack_su    0.130
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax < 18) ........       7.17 Note
PLAT234_ALERT_4_C Large Hirshfeld Difference C25A     --C26      .       0.19 Ang.
PLAT234_ALERT_4_C Large Hirshfeld Difference C26      --C25B     .       0.21 Ang.
PLAT241_ALERT_2_C High   MainMol Ueq as Compared to Neighbors of        C15 Check
PLAT241_ALERT_2_C High   MainMol Ueq as Compared to Neighbors of         C1 Check
PLAT242_ALERT_2_C Low    MainMol Ueq as Compared to Neighbors of        O13 Check
PLAT242_ALERT_2_C Low    MainMol Ueq as Compared to Neighbors of        O14 Check
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.3 Note
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.1 Note
PLAT313_ALERT_2_C Oxygen with Three Covalent Bonds (rare) ........         O1 Check
PLAT313_ALERT_2_C Oxygen with Three Covalent Bonds (rare) ........        O12 Check
PLAT355_ALERT_3_C Long   O-H (X0.82,N0.98A)  O1       - H1E      .       1.03 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  F7       ..O18A     .       2.72 Ang.
                                                      x,y,z  =      1_555 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.086 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          9 Note

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         18 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         10 Report
PLAT033_ALERT_4_G Flack x Value Deviates > 3.0 * sigma from Zero .      0.450 Note
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large       5.31 Why ?
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          7 Report
PLAT173_ALERT_4_G The CIF-Embedded .res File Contains DANG Records          7 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          3 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          1 Report
PLAT186_ALERT_4_G The CIF-Embedded .res File Contains ISOR Records          1 Report
PLAT242_ALERT_2_G Low    MainMol Ueq as Compared to Neighbors of        C13 Check
PLAT242_ALERT_2_G Low    MainMol Ueq as Compared to Neighbors of        C14 Check
PLAT242_ALERT_2_G Low    MainMol Ueq as Compared to Neighbors of        C27 Check
PLAT242_ALERT_2_G Low    MainMol Ueq as Compared to Neighbors of        C28 Check
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        22% Note
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O13            109.0 Degree
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O18B           100.9 Degree
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          9 Note
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............        217 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          9 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
  16 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  21 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  20 ALERT type 2 Indicator that the structure model may be wrong or deficient
   7 ALERT type 3 Indicator that the structure quality may be low
  10 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: RAPID-AUTO (Rigaku, 2006); cell refinement: RAPID-AUTO (Rigaku, 2006); data reduction: RAPID-AUTO (Rigaku, 2006); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b).

Hydronium bis(trifluoromethanesulfonyl)amide–18-crown-6 (1/1)

Crystal data

H3O^+·C2F6NO4S2^−·C12H24O6	F(000) = 1168
Mr = 563.48	Dx = 1.574 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 8.8341 (4) Å	Cell parameters from 22988 reflections
b = 24.3932 (9) Å	θ = 3.1–27.6°
c = 11.6111 (5) Å	µ = 0.32 mm^−1
β = 108.086 (2)°	T = 113 K
V = 2378.47 (17) Å^3	Block, colorless
Z = 4	0.50 × 0.30 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID-II diffractometer	8989 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
imaging plate scans	θmax = 26.0°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
Tmin = 0.768, Tmax = 1.000	k = −30→30
20448 measured reflections	l = −14→14
9354 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.062	w = 1/[σ^2(Fo^2) + (0.065P)^2 + 5.3126P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.162	(Δ/σ)max < 0.001
S = 1.10	Δρmax = 1.00 e Å^−3
9354 reflections	Δρmin = −0.53 e Å^−3
669 parameters	Absolute structure: Refined as an inversion twin
217 restraints	Absolute structure parameter: 0.45 (13)

Special details

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

Refinement. Refined as a 2-component inversion twin.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.0670 (10)	0.0933 (4)	−0.1013 (12)	0.066 (3)
H1A	0.057097	0.087881	−0.187835	0.079*
H1AB	−0.040231	0.101149	−0.095175	0.079*
C2	0.1339 (9)	0.0420 (4)	−0.0300 (9)	0.047 (2)
H2A	0.141282	0.046852	0.056193	0.057*
H2AB	0.064038	0.010248	−0.062655	0.057*
C3	0.3396 (10)	−0.0224 (3)	−0.0127 (10)	0.050 (2)
H3A	0.268997	−0.047567	−0.072547	0.060*
H3AB	0.333858	−0.032033	0.068611	0.060*
C4	0.5062 (11)	−0.0282 (3)	−0.0151 (10)	0.052 (2)
H4A	0.539579	−0.067114	−0.005627	0.063*
H4AB	0.516047	−0.014386	−0.092686	0.063*
C5	0.7642 (10)	0.0035 (4)	0.0872 (9)	0.050 (2)
H5A	0.774811	0.017887	0.010397	0.059*
H5AB	0.807994	−0.034182	0.099784	0.059*
C6	0.8502 (9)	0.0395 (3)	0.1906 (9)	0.049 (2)
H6A	0.829959	0.026958	0.265622	0.058*
H6AB	0.966225	0.037710	0.203504	0.058*
C7	0.8638 (10)	0.1330 (4)	0.2572 (9)	0.056 (2)
H7A	0.976004	0.123169	0.299674	0.067*
H7AB	0.804551	0.133303	0.316916	0.067*
C8	0.8551 (10)	0.1875 (4)	0.1995 (11)	0.060 (3)
H8A	0.909389	0.215113	0.260847	0.072*
H8AB	0.909252	0.186324	0.136546	0.072*
C9	0.6681 (10)	0.2461 (3)	0.0631 (8)	0.0428 (19)
H9A	0.697188	0.234582	−0.009044	0.051*
H9AB	0.736510	0.277427	0.101176	0.051*
C10	0.4992 (10)	0.2626 (3)	0.0267 (8)	0.0407 (18)
H10A	0.469132	0.272758	0.099187	0.049*
H10B	0.482402	0.294913	−0.027434	0.049*
C11	0.2374 (9)	0.2310 (3)	−0.0634 (8)	0.0420 (18)
H11A	0.214336	0.264912	−0.112523	0.050*
H11B	0.211561	0.237637	0.012539	0.050*
C12	0.1387 (9)	0.1853 (3)	−0.1316 (8)	0.0408 (18)
H12A	0.024278	0.194943	−0.154358	0.049*
H12B	0.166127	0.177644	−0.206403	0.049*
C13	0.3570 (10)	0.1603 (5)	0.2955 (8)	0.052 (2)
C14	0.5924 (8)	0.1220 (3)	0.7379 (6)	0.0290 (14)
O1	0.5005 (6)	0.1132 (2)	0.0107 (5)	0.0304 (10)
H1C	0.598 (6)	0.127 (3)	0.073 (5)	0.046*
H1D	0.431 (7)	0.142 (3)	0.028 (6)	0.046*
H1E	0.500 (9)	0.128 (3)	−0.072 (4)	0.046*
O2	0.1713 (6)	0.1382 (2)	−0.0534 (6)	0.0453 (14)
O3	0.2887 (6)	0.0330 (2)	−0.0412 (6)	0.0431 (13)
O4	0.6016 (7)	0.0036 (2)	0.0837 (6)	0.0436 (13)
O5	0.7946 (6)	0.0945 (2)	0.1632 (6)	0.0490 (15)
O6	0.6923 (6)	0.2022 (2)	0.1460 (6)	0.0497 (15)
O7	0.4007 (6)	0.2173 (2)	−0.0360 (5)	0.0367 (12)
O8	0.3018 (7)	0.0657 (2)	0.3675 (5)	0.0420 (13)
O9	0.2436 (6)	0.1455 (2)	0.4735 (5)	0.0382 (12)
O10	0.7819 (6)	0.1506 (2)	0.6270 (5)	0.0366 (11)
O11	0.5448 (6)	0.2078 (2)	0.6002 (5)	0.0420 (13)
N1	0.5279 (7)	0.1133 (3)	0.5041 (6)	0.0365 (14)
F1	0.4093 (7)	0.2104 (3)	0.3319 (6)	0.078 (2)
F2	0.2132 (7)	0.1654 (3)	0.2160 (5)	0.0706 (18)
F3	0.4538 (8)	0.1396 (4)	0.2414 (5)	0.086 (2)
F4	0.6419 (6)	0.0728 (2)	0.7592 (4)	0.0472 (12)
F5	0.6679 (6)	0.1527 (3)	0.8387 (4)	0.0525 (12)
F6	0.4344 (5)	0.1229 (3)	0.7363 (4)	0.0526 (13)
S1	0.3486 (2)	0.11734 (8)	0.42120 (16)	0.0311 (4)
S2	0.61456 (19)	0.15466 (7)	0.60634 (16)	0.0296 (4)
C15	0.0757 (19)	0.5241 (4)	0.4202 (18)	0.109 (6)
H15A	0.077681	0.512169	0.339121	0.131*
H15B	0.122820	0.561191	0.436108	0.131*
C16	−0.0919 (18)	0.5251 (5)	0.4239 (15)	0.095 (5)
H16A	−0.093031	0.531839	0.507709	0.114*
H16B	−0.152353	0.554761	0.371332	0.114*
C17	−0.3160 (12)	0.4672 (4)	0.3958 (11)	0.067 (3)
H17A	−0.388080	0.496340	0.350597	0.080*
H17B	−0.309048	0.469928	0.482380	0.080*
C18	−0.3782 (12)	0.4123 (5)	0.3473 (10)	0.064 (3)
H18A	−0.488847	0.408243	0.349433	0.077*
H18B	−0.380018	0.409422	0.261863	0.077*
C19	−0.3272 (9)	0.3177 (3)	0.3598 (8)	0.0405 (18)
H19A	−0.300690	0.315790	0.283080	0.049*
H19B	−0.443201	0.311850	0.341198	0.049*
C20	−0.2390 (10)	0.2752 (4)	0.4442 (9)	0.0459 (19)
H20A	−0.265237	0.277281	0.521009	0.055*
H20B	−0.270004	0.238405	0.408478	0.055*
C21	0.0189 (9)	0.2441 (3)	0.5509 (9)	0.0432 (19)
H21A	−0.002599	0.206788	0.515921	0.052*
H21B	−0.010505	0.244962	0.626550	0.052*
C22	0.1917 (10)	0.2577 (3)	0.5778 (8)	0.0415 (18)
H22A	0.258138	0.229553	0.631856	0.050*
H22B	0.220123	0.258542	0.501743	0.050*
C23A	0.3782 (13)	0.3235 (7)	0.7054 (12)	0.042 (4)	0.533 (13)
H23A	0.433543	0.291189	0.750923	0.051*	0.533 (13)
H23B	0.377976	0.353132	0.763601	0.051*	0.533 (13)
C23B	0.3882 (13)	0.3211 (6)	0.660 (2)	0.042 (4)	0.467 (13)
H23C	0.419774	0.313505	0.587191	0.050*	0.467 (13)
H23D	0.450638	0.296619	0.725983	0.050*	0.467 (13)
C25A	0.411 (2)	0.4465 (6)	0.6067 (16)	0.057 (3)	0.533 (13)
H25A	0.526860	0.454000	0.630793	0.068*	0.533 (13)
H25B	0.377277	0.449189	0.680189	0.068*	0.533 (13)
C25B	0.414 (3)	0.4658 (8)	0.6330 (16)	0.066 (4)	0.467 (13)
H25C	0.530931	0.467396	0.649552	0.079*	0.467 (13)
H25D	0.383820	0.480591	0.702106	0.079*	0.467 (13)
C26	0.3242 (14)	0.4894 (5)	0.5167 (12)	0.081 (3)
H26A	0.367593	0.526319	0.543631	0.098*	0.533 (13)
H26B	0.336231	0.482085	0.436116	0.098*	0.533 (13)
H26C	0.356390	0.527986	0.511347	0.098*	0.467 (13)
H26D	0.342946	0.468455	0.449385	0.098*	0.467 (13)
C27	0.1148 (9)	0.3490 (4)	0.2430 (8)	0.0421 (18)
C28	−0.0718 (9)	0.3754 (3)	−0.2055 (7)	0.0379 (17)
O12	0.0255 (6)	0.3927 (2)	0.5372 (5)	0.0325 (11)
H12C	−0.003 (9)	0.414 (3)	0.601 (5)	0.049*
H12D	0.113 (6)	0.414 (3)	0.529 (7)	0.049*
H12E	−0.066 (6)	0.398 (3)	0.467 (4)	0.049*
O13	0.1651 (10)	0.4866 (3)	0.5106 (9)	0.078 (2)
O14	−0.1628 (9)	0.4733 (3)	0.3824 (6)	0.0589 (18)
O15	−0.2840 (7)	0.3701 (2)	0.4150 (5)	0.0429 (13)
O16	−0.0720 (6)	0.2832 (2)	0.4676 (5)	0.0405 (12)
O17	0.2186 (6)	0.3097 (2)	0.6346 (6)	0.0466 (14)
O19	0.2612 (5)	0.3562 (2)	0.0831 (5)	0.0351 (11)
O20	0.2028 (7)	0.4408 (2)	0.1757 (5)	0.0431 (13)
O21	−0.0471 (6)	0.2968 (2)	−0.0511 (5)	0.0348 (11)
O22	−0.2774 (5)	0.3584 (2)	−0.0922 (5)	0.0353 (11)
C24A	0.4575 (15)	0.3420 (5)	0.6170 (12)	0.039 (3)	0.533 (13)
H24A	0.571588	0.349212	0.659214	0.047*	0.533 (13)
H24B	0.449811	0.313106	0.555715	0.047*	0.533 (13)
O18A	0.3818 (12)	0.3912 (4)	0.5588 (10)	0.042 (2)	0.533 (13)
C24B	0.4246 (19)	0.3799 (6)	0.6978 (13)	0.045 (3)	0.467 (13)
H24C	0.383639	0.389097	0.765684	0.053*	0.467 (13)
H24D	0.540929	0.386327	0.724032	0.053*	0.467 (13)
O18B	0.3470 (17)	0.4126 (6)	0.5934 (12)	0.050 (3)	0.467 (13)
N2	−0.0224 (6)	0.3950 (2)	0.0293 (5)	0.0267 (12)
F7	0.2511 (7)	0.3449 (3)	0.3368 (5)	0.075 (2)
F8	0.0674 (8)	0.2991 (2)	0.2124 (5)	0.0673 (17)
F9	0.0113 (9)	0.3734 (3)	0.2863 (6)	0.083 (2)
F10	−0.1444 (7)	0.3425 (3)	−0.2958 (4)	0.0616 (15)
F11	−0.1256 (6)	0.4256 (2)	−0.2323 (5)	0.0513 (12)
F12	0.0831 (5)	0.3750 (2)	−0.1900 (4)	0.0426 (11)
S3	0.15173 (19)	0.38867 (7)	0.12153 (15)	0.0277 (4)
S4	−0.10989 (18)	0.35095 (7)	−0.06740 (15)	0.0268 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.023 (4)	0.047 (5)	0.107 (9)	−0.009 (4)	−0.009 (5)	0.011 (5)
C2	0.019 (3)	0.044 (5)	0.076 (6)	−0.005 (3)	0.011 (4)	0.007 (4)
C3	0.039 (4)	0.021 (4)	0.091 (7)	−0.006 (3)	0.020 (4)	−0.007 (4)
C4	0.051 (5)	0.031 (4)	0.074 (6)	−0.004 (4)	0.020 (5)	−0.013 (4)
C5	0.036 (4)	0.037 (4)	0.076 (6)	0.011 (3)	0.018 (4)	0.005 (4)
C6	0.026 (4)	0.039 (4)	0.077 (6)	0.006 (3)	0.009 (4)	0.014 (4)
C7	0.029 (4)	0.058 (5)	0.064 (6)	−0.010 (4)	−0.011 (4)	−0.015 (4)
C8	0.026 (4)	0.044 (5)	0.094 (8)	−0.006 (4)	−0.003 (4)	−0.008 (5)
C9	0.049 (5)	0.035 (4)	0.046 (5)	−0.015 (3)	0.019 (4)	−0.005 (3)
C10	0.052 (5)	0.021 (4)	0.054 (5)	−0.007 (3)	0.023 (4)	−0.008 (3)
C11	0.033 (4)	0.042 (4)	0.048 (5)	0.010 (3)	0.008 (3)	0.012 (3)
C12	0.030 (4)	0.041 (4)	0.044 (4)	0.006 (3)	−0.001 (3)	0.010 (3)
C13	0.032 (4)	0.083 (7)	0.033 (4)	−0.007 (4)	0.001 (3)	0.008 (4)
C14	0.022 (3)	0.037 (4)	0.019 (3)	−0.010 (3)	−0.007 (2)	0.005 (3)
O1	0.027 (2)	0.030 (3)	0.032 (3)	0.003 (2)	0.0065 (19)	−0.002 (2)
O2	0.028 (3)	0.034 (3)	0.062 (4)	−0.002 (2)	−0.003 (2)	0.006 (3)
O3	0.032 (3)	0.031 (3)	0.069 (4)	−0.005 (2)	0.019 (3)	0.003 (3)
O4	0.033 (3)	0.034 (3)	0.067 (4)	0.003 (2)	0.020 (3)	−0.001 (3)
O5	0.027 (3)	0.040 (3)	0.066 (4)	−0.001 (2)	−0.005 (3)	−0.003 (3)
O6	0.027 (3)	0.041 (3)	0.078 (4)	−0.007 (2)	0.011 (3)	0.010 (3)
O7	0.024 (2)	0.034 (3)	0.052 (3)	0.004 (2)	0.011 (2)	−0.001 (2)
O8	0.034 (3)	0.047 (3)	0.037 (3)	−0.001 (2)	0.001 (2)	−0.009 (2)
O9	0.026 (2)	0.046 (3)	0.043 (3)	−0.003 (2)	0.012 (2)	−0.006 (2)
O10	0.024 (2)	0.042 (3)	0.043 (3)	0.005 (2)	0.009 (2)	0.007 (2)
O11	0.030 (3)	0.038 (3)	0.055 (4)	0.001 (2)	0.009 (2)	0.002 (3)
N1	0.029 (3)	0.050 (4)	0.028 (3)	0.005 (3)	0.005 (3)	−0.006 (3)
F1	0.063 (4)	0.086 (5)	0.071 (4)	−0.026 (3)	0.002 (3)	0.038 (4)
F2	0.044 (3)	0.115 (5)	0.040 (3)	0.002 (3)	−0.005 (2)	0.025 (3)
F3	0.060 (4)	0.163 (8)	0.045 (3)	0.011 (4)	0.032 (3)	0.017 (4)
F4	0.042 (3)	0.049 (3)	0.044 (3)	−0.005 (2)	0.003 (2)	0.014 (2)
F5	0.045 (3)	0.078 (4)	0.030 (2)	−0.010 (3)	0.006 (2)	−0.009 (2)
F6	0.029 (2)	0.092 (4)	0.037 (3)	−0.012 (2)	0.0116 (19)	0.001 (2)
S1	0.0234 (8)	0.0427 (10)	0.0258 (9)	−0.0008 (7)	0.0053 (6)	0.0001 (7)
S2	0.0212 (8)	0.0355 (9)	0.0309 (9)	0.0007 (7)	0.0065 (6)	0.0022 (7)
C15	0.145 (13)	0.029 (5)	0.212 (19)	0.002 (6)	0.139 (14)	0.010 (8)
C16	0.136 (12)	0.044 (6)	0.150 (13)	0.023 (7)	0.110 (11)	0.032 (7)
C17	0.047 (5)	0.064 (7)	0.085 (8)	0.033 (5)	0.014 (5)	0.004 (5)
C18	0.048 (5)	0.064 (6)	0.066 (6)	0.011 (5)	−0.002 (5)	0.000 (5)
C19	0.028 (4)	0.047 (5)	0.040 (4)	−0.004 (3)	0.002 (3)	−0.013 (3)
C20	0.035 (4)	0.045 (5)	0.056 (5)	−0.006 (3)	0.012 (4)	−0.011 (4)
C21	0.034 (4)	0.031 (4)	0.066 (6)	0.006 (3)	0.018 (4)	0.009 (4)
C22	0.037 (4)	0.035 (4)	0.052 (5)	0.006 (3)	0.012 (4)	0.006 (3)
C23A	0.029 (5)	0.051 (6)	0.038 (7)	0.005 (5)	−0.003 (5)	−0.010 (6)
C23B	0.031 (6)	0.044 (6)	0.038 (7)	0.008 (5)	−0.007 (6)	−0.005 (6)
C25A	0.040 (5)	0.070 (6)	0.064 (6)	−0.023 (5)	0.019 (5)	−0.030 (5)
C25B	0.052 (6)	0.076 (7)	0.076 (7)	−0.022 (6)	0.026 (6)	−0.024 (6)
C26	0.071 (5)	0.073 (6)	0.117 (6)	−0.030 (4)	0.054 (5)	−0.028 (5)
C27	0.034 (4)	0.052 (5)	0.042 (4)	−0.011 (4)	0.014 (3)	0.006 (4)
C28	0.031 (4)	0.046 (4)	0.040 (4)	−0.007 (3)	0.016 (3)	−0.010 (3)
O12	0.024 (2)	0.036 (3)	0.040 (3)	−0.006 (2)	0.013 (2)	−0.002 (2)
O13	0.075 (5)	0.064 (4)	0.120 (6)	−0.027 (4)	0.067 (4)	−0.022 (4)
O14	0.074 (5)	0.052 (4)	0.062 (4)	0.027 (3)	0.037 (4)	0.018 (3)
O15	0.037 (3)	0.048 (3)	0.038 (3)	0.001 (2)	0.003 (2)	−0.006 (2)
O16	0.028 (3)	0.041 (3)	0.051 (3)	0.001 (2)	0.010 (2)	0.010 (2)
O17	0.038 (3)	0.034 (3)	0.056 (4)	0.007 (2)	−0.001 (3)	−0.001 (2)
O19	0.018 (2)	0.039 (3)	0.046 (3)	0.002 (2)	0.006 (2)	−0.008 (2)
O20	0.040 (3)	0.033 (3)	0.049 (3)	−0.010 (2)	0.003 (3)	−0.010 (2)
O21	0.028 (3)	0.032 (3)	0.042 (3)	0.002 (2)	0.007 (2)	−0.004 (2)
O22	0.018 (2)	0.039 (3)	0.046 (3)	−0.004 (2)	0.005 (2)	−0.004 (2)
C24A	0.024 (5)	0.049 (5)	0.038 (5)	0.003 (4)	0.000 (4)	−0.008 (5)
O18A	0.030 (4)	0.046 (5)	0.048 (5)	−0.004 (4)	0.008 (4)	−0.002 (4)
C24B	0.031 (5)	0.053 (5)	0.045 (5)	−0.002 (5)	0.004 (4)	−0.011 (5)
O18B	0.039 (5)	0.056 (6)	0.050 (5)	−0.003 (5)	0.004 (4)	−0.015 (5)
N2	0.017 (3)	0.026 (3)	0.030 (3)	0.003 (2)	−0.002 (2)	−0.006 (2)
F7	0.064 (4)	0.093 (5)	0.041 (3)	−0.027 (3)	−0.021 (3)	0.026 (3)
F8	0.094 (4)	0.053 (3)	0.046 (3)	−0.035 (3)	0.009 (3)	0.008 (2)
F9	0.093 (5)	0.112 (6)	0.065 (4)	0.019 (4)	0.054 (4)	0.020 (4)
F10	0.072 (4)	0.080 (4)	0.030 (3)	−0.035 (3)	0.012 (2)	−0.019 (2)
F11	0.051 (3)	0.051 (3)	0.046 (3)	−0.003 (2)	0.006 (2)	0.014 (2)
F12	0.037 (2)	0.055 (3)	0.041 (3)	−0.009 (2)	0.0194 (19)	−0.005 (2)
S3	0.0204 (8)	0.0291 (8)	0.0316 (9)	−0.0015 (6)	0.0050 (6)	−0.0026 (7)
S4	0.0195 (7)	0.0288 (8)	0.0306 (8)	−0.0002 (6)	0.0056 (6)	−0.0017 (6)

Geometric parameters (Å, º)

C1—O2	1.428 (10)	C17—O14	1.418 (12)
C1—C2	1.515 (13)	C17—C18	1.489 (15)
C1—H1A	0.9900	C17—H17A	0.9900
C1—H1AB	0.9900	C17—H17B	0.9900
C2—O3	1.430 (9)	C18—O15	1.401 (11)
C2—H2A	0.9900	C18—H18A	0.9900
C2—H2AB	0.9900	C18—H18B	0.9900
C3—O3	1.431 (9)	C19—O15	1.428 (9)
C3—C4	1.487 (12)	C19—C20	1.473 (12)
C3—H3A	0.9900	C19—H19A	0.9900
C3—H3AB	0.9900	C19—H19B	0.9900
C4—O4	1.423 (11)	C20—O16	1.428 (9)
C4—H4A	0.9900	C20—H20A	0.9900
C4—H4AB	0.9900	C20—H20B	0.9900
C5—O4	1.425 (10)	C21—O16	1.418 (9)
C5—C6	1.490 (13)	C21—C22	1.497 (11)
C5—H5A	0.9900	C21—H21A	0.9900
C5—H5AB	0.9900	C21—H21B	0.9900
C6—O5	1.432 (10)	C22—O17	1.416 (10)
C6—H6A	0.9900	C22—H22A	0.9900
C6—H6AB	0.9900	C22—H22B	0.9900
C7—O5	1.426 (10)	C23A—O17	1.435 (11)
C7—C8	1.479 (14)	C23A—C24A	1.480 (11)
C7—H7A	0.9900	C23A—H23A	0.9900
C7—H7AB	0.9900	C23A—H23B	0.9900
C8—O6	1.424 (10)	C23B—O17	1.461 (11)
C8—H8A	0.9900	C23B—C24B	1.504 (13)
C8—H8AB	0.9900	C23B—H23C	0.9900
C9—O6	1.410 (10)	C23B—H23D	0.9900
C9—C10	1.475 (12)	C25A—O18A	1.451 (12)
C9—H9A	0.9900	C25A—C26	1.510 (14)
C9—H9AB	0.9900	C25A—H25A	0.9900
C10—O7	1.454 (9)	C25A—H25B	0.9900
C10—H10A	0.9900	C25B—O18B	1.440 (12)
C10—H10B	0.9900	C25B—C26	1.457 (14)
C11—O7	1.418 (9)	C25B—H25C	0.9900
C11—C12	1.483 (12)	C25B—H25D	0.9900
C11—H11A	0.9900	C26—O13	1.387 (13)
C11—H11B	0.9900	C26—H26A	0.9900
C12—O2	1.438 (9)	C26—H26B	0.9900
C12—H12A	0.9900	C26—H26C	0.9900
C12—H12B	0.9900	C26—H26D	0.9900
C13—F3	1.309 (11)	C27—F8	1.300 (10)
C13—F2	1.324 (9)	C27—F9	1.315 (11)
C13—F1	1.329 (12)	C27—F7	1.353 (9)
C13—S1	1.816 (9)	C27—S3	1.822 (8)
C14—F4	1.277 (9)	C28—F11	1.316 (10)
C14—F5	1.374 (8)	C28—F10	1.318 (9)
C14—F6	1.390 (8)	C28—F12	1.324 (9)
C14—S2	1.786 (7)	C28—S4	1.837 (8)
O1—H1C	1.00 (3)	O12—H12C	1.00 (3)
O1—H1D	1.01 (3)	O12—H12D	0.97 (3)
O1—H1E	1.03 (3)	O12—H12E	0.97 (3)
O8—S1	1.408 (6)	O19—S3	1.424 (5)
O9—S1	1.432 (5)	O20—S3	1.429 (5)
O10—S2	1.426 (5)	O21—S4	1.422 (5)
O11—S2	1.427 (6)	O22—S4	1.429 (5)
N1—S2	1.566 (7)	C24A—O18A	1.436 (11)
N1—S1	1.580 (6)	C24A—H24A	0.9900
C15—O13	1.430 (18)	C24A—H24B	0.9900
C15—C16	1.495 (18)	C24B—O18B	1.436 (12)
C15—H15A	0.9900	C24B—H24C	0.9900
C15—H15B	0.9900	C24B—H24D	0.9900
C16—O14	1.425 (15)	N2—S4	1.572 (5)
C16—H16A	0.9900	N2—S3	1.586 (5)
C16—H16B	0.9900
O2—C1—C2	108.9 (7)	O14—C17—H17A	110.1
O2—C1—H1A	109.9	C18—C17—H17A	110.1
C2—C1—H1A	109.9	O14—C17—H17B	110.1
O2—C1—H1AB	109.9	C18—C17—H17B	110.1
C2—C1—H1AB	109.9	H17A—C17—H17B	108.5
H1A—C1—H1AB	108.3	O15—C18—C17	111.3 (8)
O3—C2—C1	107.4 (7)	O15—C18—H18A	109.4
O3—C2—H2A	110.2	C17—C18—H18A	109.4
C1—C2—H2A	110.2	O15—C18—H18B	109.4
O3—C2—H2AB	110.2	C17—C18—H18B	109.4
C1—C2—H2AB	110.2	H18A—C18—H18B	108.0
H2A—C2—H2AB	108.5	O15—C19—C20	108.7 (6)
O3—C3—C4	109.1 (7)	O15—C19—H19A	110.0
O3—C3—H3A	109.9	C20—C19—H19A	110.0
C4—C3—H3A	109.9	O15—C19—H19B	110.0
O3—C3—H3AB	109.9	C20—C19—H19B	110.0
C4—C3—H3AB	109.9	H19A—C19—H19B	108.3
H3A—C3—H3AB	108.3	O16—C20—C19	109.4 (7)
O4—C4—C3	105.9 (7)	O16—C20—H20A	109.8
O4—C4—H4A	110.6	C19—C20—H20A	109.8
C3—C4—H4A	110.6	O16—C20—H20B	109.8
O4—C4—H4AB	110.6	C19—C20—H20B	109.8
C3—C4—H4AB	110.6	H20A—C20—H20B	108.3
H4A—C4—H4AB	108.7	O16—C21—C22	108.5 (6)
O4—C5—C6	106.3 (7)	O16—C21—H21A	110.0
O4—C5—H5A	110.5	C22—C21—H21A	110.0
C6—C5—H5A	110.5	O16—C21—H21B	110.0
O4—C5—H5AB	110.5	C22—C21—H21B	110.0
C6—C5—H5AB	110.5	H21A—C21—H21B	108.4
H5A—C5—H5AB	108.7	O17—C22—C21	107.9 (7)
O5—C6—C5	108.6 (7)	O17—C22—H22A	110.1
O5—C6—H6A	110.0	C21—C22—H22A	110.1
C5—C6—H6A	110.0	O17—C22—H22B	110.1
O5—C6—H6AB	110.0	C21—C22—H22B	110.1
C5—C6—H6AB	110.0	H22A—C22—H22B	108.4
H6A—C6—H6AB	108.3	O17—C23A—C24A	105.5 (10)
O5—C7—C8	107.2 (8)	O17—C23A—H23A	110.6
O5—C7—H7A	110.3	C24A—C23A—H23A	110.6
C8—C7—H7A	110.3	O17—C23A—H23B	110.6
O5—C7—H7AB	110.3	C24A—C23A—H23B	110.6
C8—C7—H7AB	110.3	H23A—C23A—H23B	108.8
H7A—C7—H7AB	108.5	O17—C23B—C24B	110.7 (11)
O6—C8—C7	109.1 (7)	O17—C23B—H23C	109.5
O6—C8—H8A	109.9	C24B—C23B—H23C	109.5
C7—C8—H8A	109.9	O17—C23B—H23D	109.5
O6—C8—H8AB	109.9	C24B—C23B—H23D	109.5
C7—C8—H8AB	109.9	H23C—C23B—H23D	108.1
H8A—C8—H8AB	108.3	O18A—C25A—C26	112.8 (12)
O6—C9—C10	109.2 (7)	O18A—C25A—H25A	109.0
O6—C9—H9A	109.8	C26—C25A—H25A	109.0
C10—C9—H9A	109.8	O18A—C25A—H25B	109.0
O6—C9—H9AB	109.8	C26—C25A—H25B	109.0
C10—C9—H9AB	109.8	H25A—C25A—H25B	107.8
H9A—C9—H9AB	108.3	O18B—C25B—C26	90.5 (12)
O7—C10—C9	109.3 (6)	O18B—C25B—H25C	113.6
O7—C10—H10A	109.8	C26—C25B—H25C	113.6
C9—C10—H10A	109.8	O18B—C25B—H25D	113.6
O7—C10—H10B	109.8	C26—C25B—H25D	113.6
C9—C10—H10B	109.8	H25C—C25B—H25D	110.8
H10A—C10—H10B	108.3	O13—C26—C25B	106.3 (14)
O7—C11—C12	109.4 (7)	O13—C26—C25A	106.9 (12)
O7—C11—H11A	109.8	O13—C26—H26A	110.3
C12—C11—H11A	109.8	C25A—C26—H26A	110.3
O7—C11—H11B	109.8	O13—C26—H26B	110.3
C12—C11—H11B	109.8	C25A—C26—H26B	110.3
H11A—C11—H11B	108.2	H26A—C26—H26B	108.6
O2—C12—C11	107.1 (6)	O13—C26—H26C	110.5
O2—C12—H12A	110.3	C25B—C26—H26C	110.5
C11—C12—H12A	110.3	O13—C26—H26D	110.5
O2—C12—H12B	110.3	C25B—C26—H26D	110.5
C11—C12—H12B	110.3	H26C—C26—H26D	108.7
H12A—C12—H12B	108.5	F8—C27—F9	109.0 (7)
F3—C13—F2	109.3 (7)	F8—C27—F7	106.4 (8)
F3—C13—F1	107.0 (8)	F9—C27—F7	106.1 (8)
F2—C13—F1	107.3 (9)	F8—C27—S3	113.9 (6)
F3—C13—S1	111.0 (7)	F9—C27—S3	111.6 (6)
F2—C13—S1	110.2 (6)	F7—C27—S3	109.5 (5)
F1—C13—S1	111.8 (6)	F11—C28—F10	109.1 (7)
F4—C14—F5	107.5 (6)	F11—C28—F12	108.8 (6)
F4—C14—F6	107.4 (6)	F10—C28—F12	109.3 (6)
F5—C14—F6	102.9 (6)	F11—C28—S4	111.0 (5)
F4—C14—S2	117.6 (6)	F10—C28—S4	108.7 (5)
F5—C14—S2	109.5 (5)	F12—C28—S4	109.9 (6)
F6—C14—S2	111.0 (4)	H12C—O12—H12D	101 (5)
H1C—O1—H1D	93 (4)	H12C—O12—H12E	103 (5)
H1C—O1—H1E	108 (5)	H12D—O12—H12E	110 (5)
H1D—O1—H1E	97 (4)	C26—O13—C15	109.0 (9)
C1—O2—C12	112.9 (6)	C17—O14—C16	113.0 (8)
C2—O3—C3	111.4 (6)	C18—O15—C19	112.1 (7)
C4—O4—C5	111.2 (7)	C21—O16—C20	111.7 (6)
C7—O5—C6	114.3 (7)	C22—O17—C23A	118.1 (9)
C9—O6—C8	114.0 (7)	C22—O17—C23B	106.2 (8)
C11—O7—C10	110.0 (6)	O18A—C24A—C23A	109.3 (10)
S2—N1—S1	125.7 (4)	O18A—C24A—H24A	109.8
O8—S1—O9	118.5 (3)	C23A—C24A—H24A	109.8
O8—S1—N1	108.3 (4)	O18A—C24A—H24B	109.8
O9—S1—N1	115.5 (3)	C23A—C24A—H24B	109.8
O8—S1—C13	103.9 (4)	H24A—C24A—H24B	108.3
O9—S1—C13	104.9 (4)	C24A—O18A—C25A	126.5 (11)
N1—S1—C13	104.1 (4)	O18B—C24B—C23B	106.5 (11)
O10—S2—O11	118.7 (3)	O18B—C24B—H24C	110.4
O10—S2—N1	108.7 (3)	C23B—C24B—H24C	110.4
O11—S2—N1	116.5 (3)	O18B—C24B—H24D	110.4
O10—S2—C14	102.1 (3)	C23B—C24B—H24D	110.4
O11—S2—C14	106.7 (4)	H24C—C24B—H24D	108.6
N1—S2—C14	101.7 (3)	C24B—O18B—C25B	101.0 (11)
O13—C15—C16	108.4 (10)	S4—N2—S3	125.1 (4)
O13—C15—H15A	110.0	O19—S3—O20	118.7 (3)
C16—C15—H15A	110.0	O19—S3—N2	116.9 (3)
O13—C15—H15B	110.0	O20—S3—N2	108.6 (3)
C16—C15—H15B	110.0	O19—S3—C27	104.5 (4)
H15A—C15—H15B	108.4	O20—S3—C27	103.9 (4)
O14—C16—C15	108.1 (9)	N2—S3—C27	101.8 (3)
O14—C16—H16A	110.1	O21—S4—O22	118.8 (3)
C15—C16—H16A	110.1	O21—S4—N2	117.0 (3)
O14—C16—H16B	110.1	O22—S4—N2	107.8 (3)
C15—C16—H16B	110.1	O21—S4—C28	104.3 (3)
H16A—C16—H16B	108.4	O22—S4—C28	104.0 (3)
O14—C17—C18	107.8 (8)	N2—S4—C28	102.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1C···O5	1.00 (3)	1.90 (6)	2.690 (7)	134 (6)
O1—H1C···O6	1.00 (3)	2.08 (6)	2.898 (8)	138 (6)
O1—H1D···O2	1.01 (3)	2.19 (7)	2.835 (7)	120 (5)
O1—H1D···O7	1.01 (3)	1.96 (7)	2.687 (7)	127 (6)
O1—H1E···F5^i	1.03 (3)	2.14 (6)	2.989 (7)	139 (6)
O1—H1E···F6^i	1.03 (3)	2.12 (4)	3.065 (7)	152 (6)
O12—H12C···F11^ii	1.00 (3)	2.50 (4)	3.436 (8)	154 (7)
O12—H12D···O13	0.97 (3)	1.85 (6)	2.666 (9)	140 (7)
O12—H12D···O18A	0.97 (3)	2.36 (6)	3.079 (12)	131 (6)
O12—H12D···O18B	0.97 (3)	1.97 (6)	2.753 (15)	137 (7)
O12—H12E···O14	0.97 (3)	2.14 (7)	2.831 (8)	128 (6)
O12—H12E···O15	0.97 (3)	1.95 (6)	2.718 (7)	135 (6)

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