organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2414-3146

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

aDepartment of Materials Science and Engineering, Kyoto University, 36-1, Yoshida-honmachi, Sakyo-ku, Kyoto 606-8501, Japan, bDepartment of Applied Chemistry, Faculty of Engineering, Sanyo-Onoda City University, 1-1-1, Daigakudori, Sanyo-Onoda, Yamaguchi, 756-0884, Japan, and cDepartment of Fundamental Energy Science, Graduate School of Energy Science, Kyoto University, 36-1, Yoshida-honmachi, Sakyo-ku, Kyoto 606-8501, Japan
*Correspondence e-mail: kitada.atsushi.3r@kyoto-u.ac.jp

Edited by H. Ishida, Okayama University, Japan (Received 27 January 2020; accepted 5 February 2020; online 6 February 2020)

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).

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Hydro­nium·18-crown-6 bis­(tri­fluoro­methane­sulfon­yl)amide is an ionized form of ternary equimolar mixture of 18-crown-6, imide superacid and water, the molten salt of which is known as a hydro­nium solvate ionic liquid (m.p. 341 −343 K) with very strong Brønsted acidity (Kitada et al., 2018[Kitada, A., Takeoka, S., Kintsu, K., Fukami, K., Saimura, M., Nagata, T., Katahira, M. & Murase, K. (2018). J. Electrochem. Soc. 165, H121-H127.]). The title compound crystallizes in the monoclinic space group P21. The asymmetric unit contains two crystallographically independent ion-pairs (Fig. 1[link]); each 18-crown-6 mol­ecule complexes with a hydro­nium ion. One of the 18-crown-6 mol­ecules exhibits conformational disorder. The two bis­(tri­fluoro­methane­sulfon­yl)amide anions adopt a transoid conformation. The complex cations and anions are arranged alternately along the c axis to form columns (Fig. 2[link]). 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 18-crown-6 mol­ecule with 1.85 (6)–2.36 (6) Å distances (Table 1[link]). The hydro­nium ion complexed with the ordered crown inter­acts with two anions via O—H⋯F hydrogen bonds with H2OH⋯F3C distances of 2.12 (4)–2.14 (6) Å, while the hydro­nium ion with the disordered crown exhibits a weak O—H⋯F inter­action [H⋯F = 2.50 (4) Å].

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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⋯F5i 1.03 (3) 2.14 (6) 2.989 (7) 139 (6)
O1—H1E⋯F6i 1.03 (3) 2.12 (4) 3.065 (7) 152 (6)
O12—H12C⋯F11ii 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.
[Figure 1]
Figure 1
The asymmetric unit of the title compound, showing the two crystallographically independent ion-pairs. Displacement ellipsoids are shown at the 50% probability level and hydrogen atoms of 18-crown-6 are omitted for clarity. Dashed lines represent hydrogen bonds.
[Figure 2]
Figure 2
Structure of the title compound viewed along (a) the a axis and (b) the c axis. Hydrogen atoms of 18-crown-6 are omitted for clarity.

Synthesis and crystallization

The polycrystalline title compound was synthesized according to a previous report (Kitada et al., 2018[Kitada, A., Takeoka, S., Kintsu, K., Fukami, K., Saimura, M., Nagata, T., Katahira, M. & Murase, K. (2018). J. Electrochem. Soc. 165, H121-H127.]). The powder sample was dissolved in copious amounts of water and stored in a plastic-wrapped Petri dish. Single crystals of the title compound were prepared by slow evaporation as colorless prisms.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. The structure was refined as an inversion twin. Restraints (SADI, DFIX, DANG, SIMU and ISOR) were used to correct the geometry of the disordered crown ether mol­ecule and hydro­nium ion, and the displacement parameters of the disordered crown ether mol­ecule.

Table 2
Experimental details

Crystal data
Chemical formula H3O+·C2F6NO4S2·C12H24O6
Mr 563.48
Crystal system, space group Monoclinic, P21
Temperature (K) 113
a, b, c (Å) 8.8341 (4), 24.3932 (9), 11.6111 (5)
β (°) 108.086 (2)
V3) 2378.47 (17)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.32
Crystal size (mm) 0.50 × 0.30 × 0.20
 
Data collection
Diffractometer Rigaku R-AXIS RAPID-II
Absorption correction Multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.])
Tmin, Tmax 0.768, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 20448, 9354, 8989
Rint 0.027
(sin θ/λ)max−1) 0.617
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.062, 0.162, 1.10
No. of reflections 9354
No. of parameters 669
No. of restraints 217
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 1.00, −0.54
Absolute structure Refined as an inversion twin
Absolute structure parameter 0.45 (13)
Computer programs: RAPID-AUTO (Rigaku, 2006[Rigaku (2006). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]) and SHELXL2018 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]).

Structural data


Computing details top

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) top
Crystal data top
H3O+·C2F6NO4S2·C12H24O6F(000) = 1168
Mr = 563.48Dx = 1.574 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 8.8341 (4) ÅCell parameters from 22988 reflections
b = 24.3932 (9) Åθ = 3.1–27.6°
c = 11.6111 (5) ŵ = 0.32 mm1
β = 108.086 (2)°T = 113 K
V = 2378.47 (17) Å3Block, colorless
Z = 40.50 × 0.30 × 0.20 mm
Data collection top
Rigaku R-AXIS RAPID-II
diffractometer
8989 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.027
imaging plate scansθmax = 26.0°, θmin = 3.1°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1010
Tmin = 0.768, Tmax = 1.000k = 3030
20448 measured reflectionsl = 1414
9354 independent reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.062 w = 1/[σ2(Fo2) + (0.065P)2 + 5.3126P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.162(Δ/σ)max < 0.001
S = 1.10Δρmax = 1.00 e Å3
9354 reflectionsΔρmin = 0.53 e Å3
669 parametersAbsolute structure: Refined as an inversion twin
217 restraintsAbsolute structure parameter: 0.45 (13)
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.0670 (10)0.0933 (4)0.1013 (12)0.066 (3)
H1A0.0570970.0878810.1878350.079*
H1AB0.0402310.1011490.0951750.079*
C20.1339 (9)0.0420 (4)0.0300 (9)0.047 (2)
H2A0.1412820.0468520.0561930.057*
H2AB0.0640380.0102480.0626550.057*
C30.3396 (10)0.0224 (3)0.0127 (10)0.050 (2)
H3A0.2689970.0475670.0725470.060*
H3AB0.3338580.0320330.0686110.060*
C40.5062 (11)0.0282 (3)0.0151 (10)0.052 (2)
H4A0.5395790.0671140.0056270.063*
H4AB0.5160470.0143860.0926860.063*
C50.7642 (10)0.0035 (4)0.0872 (9)0.050 (2)
H5A0.7748110.0178870.0103970.059*
H5AB0.8079940.0341820.0997840.059*
C60.8502 (9)0.0395 (3)0.1906 (9)0.049 (2)
H6A0.8299590.0269580.2656220.058*
H6AB0.9662250.0377100.2035040.058*
C70.8638 (10)0.1330 (4)0.2572 (9)0.056 (2)
H7A0.9760040.1231690.2996740.067*
H7AB0.8045510.1333030.3169160.067*
C80.8551 (10)0.1875 (4)0.1995 (11)0.060 (3)
H8A0.9093890.2151130.2608470.072*
H8AB0.9092520.1863240.1365460.072*
C90.6681 (10)0.2461 (3)0.0631 (8)0.0428 (19)
H9A0.6971880.2345820.0090440.051*
H9AB0.7365100.2774270.1011760.051*
C100.4992 (10)0.2626 (3)0.0267 (8)0.0407 (18)
H10A0.4691320.2727580.0991870.049*
H10B0.4824020.2949130.0274340.049*
C110.2374 (9)0.2310 (3)0.0634 (8)0.0420 (18)
H11A0.2143360.2649120.1125230.050*
H11B0.2115610.2376370.0125390.050*
C120.1387 (9)0.1853 (3)0.1316 (8)0.0408 (18)
H12A0.0242780.1949430.1543580.049*
H12B0.1661270.1776440.2064030.049*
C130.3570 (10)0.1603 (5)0.2955 (8)0.052 (2)
C140.5924 (8)0.1220 (3)0.7379 (6)0.0290 (14)
O10.5005 (6)0.1132 (2)0.0107 (5)0.0304 (10)
H1C0.598 (6)0.127 (3)0.073 (5)0.046*
H1D0.431 (7)0.142 (3)0.028 (6)0.046*
H1E0.500 (9)0.128 (3)0.072 (4)0.046*
O20.1713 (6)0.1382 (2)0.0534 (6)0.0453 (14)
O30.2887 (6)0.0330 (2)0.0412 (6)0.0431 (13)
O40.6016 (7)0.0036 (2)0.0837 (6)0.0436 (13)
O50.7946 (6)0.0945 (2)0.1632 (6)0.0490 (15)
O60.6923 (6)0.2022 (2)0.1460 (6)0.0497 (15)
O70.4007 (6)0.2173 (2)0.0360 (5)0.0367 (12)
O80.3018 (7)0.0657 (2)0.3675 (5)0.0420 (13)
O90.2436 (6)0.1455 (2)0.4735 (5)0.0382 (12)
O100.7819 (6)0.1506 (2)0.6270 (5)0.0366 (11)
O110.5448 (6)0.2078 (2)0.6002 (5)0.0420 (13)
N10.5279 (7)0.1133 (3)0.5041 (6)0.0365 (14)
F10.4093 (7)0.2104 (3)0.3319 (6)0.078 (2)
F20.2132 (7)0.1654 (3)0.2160 (5)0.0706 (18)
F30.4538 (8)0.1396 (4)0.2414 (5)0.086 (2)
F40.6419 (6)0.0728 (2)0.7592 (4)0.0472 (12)
F50.6679 (6)0.1527 (3)0.8387 (4)0.0525 (12)
F60.4344 (5)0.1229 (3)0.7363 (4)0.0526 (13)
S10.3486 (2)0.11734 (8)0.42120 (16)0.0311 (4)
S20.61456 (19)0.15466 (7)0.60634 (16)0.0296 (4)
C150.0757 (19)0.5241 (4)0.4202 (18)0.109 (6)
H15A0.0776810.5121690.3391210.131*
H15B0.1228200.5611910.4361080.131*
C160.0919 (18)0.5251 (5)0.4239 (15)0.095 (5)
H16A0.0930310.5318390.5077090.114*
H16B0.1523530.5547610.3713320.114*
C170.3160 (12)0.4672 (4)0.3958 (11)0.067 (3)
H17A0.3880800.4963400.3505970.080*
H17B0.3090480.4699280.4823800.080*
C180.3782 (12)0.4123 (5)0.3473 (10)0.064 (3)
H18A0.4888470.4082430.3494330.077*
H18B0.3800180.4094220.2618630.077*
C190.3272 (9)0.3177 (3)0.3598 (8)0.0405 (18)
H19A0.3006900.3157900.2830800.049*
H19B0.4432010.3118500.3411980.049*
C200.2390 (10)0.2752 (4)0.4442 (9)0.0459 (19)
H20A0.2652370.2772810.5210090.055*
H20B0.2700040.2384050.4084780.055*
C210.0189 (9)0.2441 (3)0.5509 (9)0.0432 (19)
H21A0.0025990.2067880.5159210.052*
H21B0.0105050.2449620.6265500.052*
C220.1917 (10)0.2577 (3)0.5778 (8)0.0415 (18)
H22A0.2581380.2295530.6318560.050*
H22B0.2201230.2585420.5017430.050*
C23A0.3782 (13)0.3235 (7)0.7054 (12)0.042 (4)0.533 (13)
H23A0.4335430.2911890.7509230.051*0.533 (13)
H23B0.3779760.3531320.7636010.051*0.533 (13)
C23B0.3882 (13)0.3211 (6)0.660 (2)0.042 (4)0.467 (13)
H23C0.4197740.3135050.5871910.050*0.467 (13)
H23D0.4506380.2966190.7259830.050*0.467 (13)
C25A0.411 (2)0.4465 (6)0.6067 (16)0.057 (3)0.533 (13)
H25A0.5268600.4540000.6307930.068*0.533 (13)
H25B0.3772770.4491890.6801890.068*0.533 (13)
C25B0.414 (3)0.4658 (8)0.6330 (16)0.066 (4)0.467 (13)
H25C0.5309310.4673960.6495520.079*0.467 (13)
H25D0.3838200.4805910.7021060.079*0.467 (13)
C260.3242 (14)0.4894 (5)0.5167 (12)0.081 (3)
H26A0.3675930.5263190.5436310.098*0.533 (13)
H26B0.3362310.4820850.4361160.098*0.533 (13)
H26C0.3563900.5279860.5113470.098*0.467 (13)
H26D0.3429460.4684550.4493850.098*0.467 (13)
C270.1148 (9)0.3490 (4)0.2430 (8)0.0421 (18)
C280.0718 (9)0.3754 (3)0.2055 (7)0.0379 (17)
O120.0255 (6)0.3927 (2)0.5372 (5)0.0325 (11)
H12C0.003 (9)0.414 (3)0.601 (5)0.049*
H12D0.113 (6)0.414 (3)0.529 (7)0.049*
H12E0.066 (6)0.398 (3)0.467 (4)0.049*
O130.1651 (10)0.4866 (3)0.5106 (9)0.078 (2)
O140.1628 (9)0.4733 (3)0.3824 (6)0.0589 (18)
O150.2840 (7)0.3701 (2)0.4150 (5)0.0429 (13)
O160.0720 (6)0.2832 (2)0.4676 (5)0.0405 (12)
O170.2186 (6)0.3097 (2)0.6346 (6)0.0466 (14)
O190.2612 (5)0.3562 (2)0.0831 (5)0.0351 (11)
O200.2028 (7)0.4408 (2)0.1757 (5)0.0431 (13)
O210.0471 (6)0.2968 (2)0.0511 (5)0.0348 (11)
O220.2774 (5)0.3584 (2)0.0922 (5)0.0353 (11)
C24A0.4575 (15)0.3420 (5)0.6170 (12)0.039 (3)0.533 (13)
H24A0.5715880.3492120.6592140.047*0.533 (13)
H24B0.4498110.3131060.5557150.047*0.533 (13)
O18A0.3818 (12)0.3912 (4)0.5588 (10)0.042 (2)0.533 (13)
C24B0.4246 (19)0.3799 (6)0.6978 (13)0.045 (3)0.467 (13)
H24C0.3836390.3890970.7656840.053*0.467 (13)
H24D0.5409290.3863270.7240320.053*0.467 (13)
O18B0.3470 (17)0.4126 (6)0.5934 (12)0.050 (3)0.467 (13)
N20.0224 (6)0.3950 (2)0.0293 (5)0.0267 (12)
F70.2511 (7)0.3449 (3)0.3368 (5)0.075 (2)
F80.0674 (8)0.2991 (2)0.2124 (5)0.0673 (17)
F90.0113 (9)0.3734 (3)0.2863 (6)0.083 (2)
F100.1444 (7)0.3425 (3)0.2958 (4)0.0616 (15)
F110.1256 (6)0.4256 (2)0.2323 (5)0.0513 (12)
F120.0831 (5)0.3750 (2)0.1900 (4)0.0426 (11)
S30.15173 (19)0.38867 (7)0.12153 (15)0.0277 (4)
S40.10989 (18)0.35095 (7)0.06740 (15)0.0268 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.023 (4)0.047 (5)0.107 (9)0.009 (4)0.009 (5)0.011 (5)
C20.019 (3)0.044 (5)0.076 (6)0.005 (3)0.011 (4)0.007 (4)
C30.039 (4)0.021 (4)0.091 (7)0.006 (3)0.020 (4)0.007 (4)
C40.051 (5)0.031 (4)0.074 (6)0.004 (4)0.020 (5)0.013 (4)
C50.036 (4)0.037 (4)0.076 (6)0.011 (3)0.018 (4)0.005 (4)
C60.026 (4)0.039 (4)0.077 (6)0.006 (3)0.009 (4)0.014 (4)
C70.029 (4)0.058 (5)0.064 (6)0.010 (4)0.011 (4)0.015 (4)
C80.026 (4)0.044 (5)0.094 (8)0.006 (4)0.003 (4)0.008 (5)
C90.049 (5)0.035 (4)0.046 (5)0.015 (3)0.019 (4)0.005 (3)
C100.052 (5)0.021 (4)0.054 (5)0.007 (3)0.023 (4)0.008 (3)
C110.033 (4)0.042 (4)0.048 (5)0.010 (3)0.008 (3)0.012 (3)
C120.030 (4)0.041 (4)0.044 (4)0.006 (3)0.001 (3)0.010 (3)
C130.032 (4)0.083 (7)0.033 (4)0.007 (4)0.001 (3)0.008 (4)
C140.022 (3)0.037 (4)0.019 (3)0.010 (3)0.007 (2)0.005 (3)
O10.027 (2)0.030 (3)0.032 (3)0.003 (2)0.0065 (19)0.002 (2)
O20.028 (3)0.034 (3)0.062 (4)0.002 (2)0.003 (2)0.006 (3)
O30.032 (3)0.031 (3)0.069 (4)0.005 (2)0.019 (3)0.003 (3)
O40.033 (3)0.034 (3)0.067 (4)0.003 (2)0.020 (3)0.001 (3)
O50.027 (3)0.040 (3)0.066 (4)0.001 (2)0.005 (3)0.003 (3)
O60.027 (3)0.041 (3)0.078 (4)0.007 (2)0.011 (3)0.010 (3)
O70.024 (2)0.034 (3)0.052 (3)0.004 (2)0.011 (2)0.001 (2)
O80.034 (3)0.047 (3)0.037 (3)0.001 (2)0.001 (2)0.009 (2)
O90.026 (2)0.046 (3)0.043 (3)0.003 (2)0.012 (2)0.006 (2)
O100.024 (2)0.042 (3)0.043 (3)0.005 (2)0.009 (2)0.007 (2)
O110.030 (3)0.038 (3)0.055 (4)0.001 (2)0.009 (2)0.002 (3)
N10.029 (3)0.050 (4)0.028 (3)0.005 (3)0.005 (3)0.006 (3)
F10.063 (4)0.086 (5)0.071 (4)0.026 (3)0.002 (3)0.038 (4)
F20.044 (3)0.115 (5)0.040 (3)0.002 (3)0.005 (2)0.025 (3)
F30.060 (4)0.163 (8)0.045 (3)0.011 (4)0.032 (3)0.017 (4)
F40.042 (3)0.049 (3)0.044 (3)0.005 (2)0.003 (2)0.014 (2)
F50.045 (3)0.078 (4)0.030 (2)0.010 (3)0.006 (2)0.009 (2)
F60.029 (2)0.092 (4)0.037 (3)0.012 (2)0.0116 (19)0.001 (2)
S10.0234 (8)0.0427 (10)0.0258 (9)0.0008 (7)0.0053 (6)0.0001 (7)
S20.0212 (8)0.0355 (9)0.0309 (9)0.0007 (7)0.0065 (6)0.0022 (7)
C150.145 (13)0.029 (5)0.212 (19)0.002 (6)0.139 (14)0.010 (8)
C160.136 (12)0.044 (6)0.150 (13)0.023 (7)0.110 (11)0.032 (7)
C170.047 (5)0.064 (7)0.085 (8)0.033 (5)0.014 (5)0.004 (5)
C180.048 (5)0.064 (6)0.066 (6)0.011 (5)0.002 (5)0.000 (5)
C190.028 (4)0.047 (5)0.040 (4)0.004 (3)0.002 (3)0.013 (3)
C200.035 (4)0.045 (5)0.056 (5)0.006 (3)0.012 (4)0.011 (4)
C210.034 (4)0.031 (4)0.066 (6)0.006 (3)0.018 (4)0.009 (4)
C220.037 (4)0.035 (4)0.052 (5)0.006 (3)0.012 (4)0.006 (3)
C23A0.029 (5)0.051 (6)0.038 (7)0.005 (5)0.003 (5)0.010 (6)
C23B0.031 (6)0.044 (6)0.038 (7)0.008 (5)0.007 (6)0.005 (6)
C25A0.040 (5)0.070 (6)0.064 (6)0.023 (5)0.019 (5)0.030 (5)
C25B0.052 (6)0.076 (7)0.076 (7)0.022 (6)0.026 (6)0.024 (6)
C260.071 (5)0.073 (6)0.117 (6)0.030 (4)0.054 (5)0.028 (5)
C270.034 (4)0.052 (5)0.042 (4)0.011 (4)0.014 (3)0.006 (4)
C280.031 (4)0.046 (4)0.040 (4)0.007 (3)0.016 (3)0.010 (3)
O120.024 (2)0.036 (3)0.040 (3)0.006 (2)0.013 (2)0.002 (2)
O130.075 (5)0.064 (4)0.120 (6)0.027 (4)0.067 (4)0.022 (4)
O140.074 (5)0.052 (4)0.062 (4)0.027 (3)0.037 (4)0.018 (3)
O150.037 (3)0.048 (3)0.038 (3)0.001 (2)0.003 (2)0.006 (2)
O160.028 (3)0.041 (3)0.051 (3)0.001 (2)0.010 (2)0.010 (2)
O170.038 (3)0.034 (3)0.056 (4)0.007 (2)0.001 (3)0.001 (2)
O190.018 (2)0.039 (3)0.046 (3)0.002 (2)0.006 (2)0.008 (2)
O200.040 (3)0.033 (3)0.049 (3)0.010 (2)0.003 (3)0.010 (2)
O210.028 (3)0.032 (3)0.042 (3)0.002 (2)0.007 (2)0.004 (2)
O220.018 (2)0.039 (3)0.046 (3)0.004 (2)0.005 (2)0.004 (2)
C24A0.024 (5)0.049 (5)0.038 (5)0.003 (4)0.000 (4)0.008 (5)
O18A0.030 (4)0.046 (5)0.048 (5)0.004 (4)0.008 (4)0.002 (4)
C24B0.031 (5)0.053 (5)0.045 (5)0.002 (5)0.004 (4)0.011 (5)
O18B0.039 (5)0.056 (6)0.050 (5)0.003 (5)0.004 (4)0.015 (5)
N20.017 (3)0.026 (3)0.030 (3)0.003 (2)0.002 (2)0.006 (2)
F70.064 (4)0.093 (5)0.041 (3)0.027 (3)0.021 (3)0.026 (3)
F80.094 (4)0.053 (3)0.046 (3)0.035 (3)0.009 (3)0.008 (2)
F90.093 (5)0.112 (6)0.065 (4)0.019 (4)0.054 (4)0.020 (4)
F100.072 (4)0.080 (4)0.030 (3)0.035 (3)0.012 (2)0.019 (2)
F110.051 (3)0.051 (3)0.046 (3)0.003 (2)0.006 (2)0.014 (2)
F120.037 (2)0.055 (3)0.041 (3)0.009 (2)0.0194 (19)0.005 (2)
S30.0204 (8)0.0291 (8)0.0316 (9)0.0015 (6)0.0050 (6)0.0026 (7)
S40.0195 (7)0.0288 (8)0.0306 (8)0.0002 (6)0.0056 (6)0.0017 (6)
Geometric parameters (Å, º) top
C1—O21.428 (10)C17—O141.418 (12)
C1—C21.515 (13)C17—C181.489 (15)
C1—H1A0.9900C17—H17A0.9900
C1—H1AB0.9900C17—H17B0.9900
C2—O31.430 (9)C18—O151.401 (11)
C2—H2A0.9900C18—H18A0.9900
C2—H2AB0.9900C18—H18B0.9900
C3—O31.431 (9)C19—O151.428 (9)
C3—C41.487 (12)C19—C201.473 (12)
C3—H3A0.9900C19—H19A0.9900
C3—H3AB0.9900C19—H19B0.9900
C4—O41.423 (11)C20—O161.428 (9)
C4—H4A0.9900C20—H20A0.9900
C4—H4AB0.9900C20—H20B0.9900
C5—O41.425 (10)C21—O161.418 (9)
C5—C61.490 (13)C21—C221.497 (11)
C5—H5A0.9900C21—H21A0.9900
C5—H5AB0.9900C21—H21B0.9900
C6—O51.432 (10)C22—O171.416 (10)
C6—H6A0.9900C22—H22A0.9900
C6—H6AB0.9900C22—H22B0.9900
C7—O51.426 (10)C23A—O171.435 (11)
C7—C81.479 (14)C23A—C24A1.480 (11)
C7—H7A0.9900C23A—H23A0.9900
C7—H7AB0.9900C23A—H23B0.9900
C8—O61.424 (10)C23B—O171.461 (11)
C8—H8A0.9900C23B—C24B1.504 (13)
C8—H8AB0.9900C23B—H23C0.9900
C9—O61.410 (10)C23B—H23D0.9900
C9—C101.475 (12)C25A—O18A1.451 (12)
C9—H9A0.9900C25A—C261.510 (14)
C9—H9AB0.9900C25A—H25A0.9900
C10—O71.454 (9)C25A—H25B0.9900
C10—H10A0.9900C25B—O18B1.440 (12)
C10—H10B0.9900C25B—C261.457 (14)
C11—O71.418 (9)C25B—H25C0.9900
C11—C121.483 (12)C25B—H25D0.9900
C11—H11A0.9900C26—O131.387 (13)
C11—H11B0.9900C26—H26A0.9900
C12—O21.438 (9)C26—H26B0.9900
C12—H12A0.9900C26—H26C0.9900
C12—H12B0.9900C26—H26D0.9900
C13—F31.309 (11)C27—F81.300 (10)
C13—F21.324 (9)C27—F91.315 (11)
C13—F11.329 (12)C27—F71.353 (9)
C13—S11.816 (9)C27—S31.822 (8)
C14—F41.277 (9)C28—F111.316 (10)
C14—F51.374 (8)C28—F101.318 (9)
C14—F61.390 (8)C28—F121.324 (9)
C14—S21.786 (7)C28—S41.837 (8)
O1—H1C1.00 (3)O12—H12C1.00 (3)
O1—H1D1.01 (3)O12—H12D0.97 (3)
O1—H1E1.03 (3)O12—H12E0.97 (3)
O8—S11.408 (6)O19—S31.424 (5)
O9—S11.432 (5)O20—S31.429 (5)
O10—S21.426 (5)O21—S41.422 (5)
O11—S21.427 (6)O22—S41.429 (5)
N1—S21.566 (7)C24A—O18A1.436 (11)
N1—S11.580 (6)C24A—H24A0.9900
C15—O131.430 (18)C24A—H24B0.9900
C15—C161.495 (18)C24B—O18B1.436 (12)
C15—H15A0.9900C24B—H24C0.9900
C15—H15B0.9900C24B—H24D0.9900
C16—O141.425 (15)N2—S41.572 (5)
C16—H16A0.9900N2—S31.586 (5)
C16—H16B0.9900
O2—C1—C2108.9 (7)O14—C17—H17A110.1
O2—C1—H1A109.9C18—C17—H17A110.1
C2—C1—H1A109.9O14—C17—H17B110.1
O2—C1—H1AB109.9C18—C17—H17B110.1
C2—C1—H1AB109.9H17A—C17—H17B108.5
H1A—C1—H1AB108.3O15—C18—C17111.3 (8)
O3—C2—C1107.4 (7)O15—C18—H18A109.4
O3—C2—H2A110.2C17—C18—H18A109.4
C1—C2—H2A110.2O15—C18—H18B109.4
O3—C2—H2AB110.2C17—C18—H18B109.4
C1—C2—H2AB110.2H18A—C18—H18B108.0
H2A—C2—H2AB108.5O15—C19—C20108.7 (6)
O3—C3—C4109.1 (7)O15—C19—H19A110.0
O3—C3—H3A109.9C20—C19—H19A110.0
C4—C3—H3A109.9O15—C19—H19B110.0
O3—C3—H3AB109.9C20—C19—H19B110.0
C4—C3—H3AB109.9H19A—C19—H19B108.3
H3A—C3—H3AB108.3O16—C20—C19109.4 (7)
O4—C4—C3105.9 (7)O16—C20—H20A109.8
O4—C4—H4A110.6C19—C20—H20A109.8
C3—C4—H4A110.6O16—C20—H20B109.8
O4—C4—H4AB110.6C19—C20—H20B109.8
C3—C4—H4AB110.6H20A—C20—H20B108.3
H4A—C4—H4AB108.7O16—C21—C22108.5 (6)
O4—C5—C6106.3 (7)O16—C21—H21A110.0
O4—C5—H5A110.5C22—C21—H21A110.0
C6—C5—H5A110.5O16—C21—H21B110.0
O4—C5—H5AB110.5C22—C21—H21B110.0
C6—C5—H5AB110.5H21A—C21—H21B108.4
H5A—C5—H5AB108.7O17—C22—C21107.9 (7)
O5—C6—C5108.6 (7)O17—C22—H22A110.1
O5—C6—H6A110.0C21—C22—H22A110.1
C5—C6—H6A110.0O17—C22—H22B110.1
O5—C6—H6AB110.0C21—C22—H22B110.1
C5—C6—H6AB110.0H22A—C22—H22B108.4
H6A—C6—H6AB108.3O17—C23A—C24A105.5 (10)
O5—C7—C8107.2 (8)O17—C23A—H23A110.6
O5—C7—H7A110.3C24A—C23A—H23A110.6
C8—C7—H7A110.3O17—C23A—H23B110.6
O5—C7—H7AB110.3C24A—C23A—H23B110.6
C8—C7—H7AB110.3H23A—C23A—H23B108.8
H7A—C7—H7AB108.5O17—C23B—C24B110.7 (11)
O6—C8—C7109.1 (7)O17—C23B—H23C109.5
O6—C8—H8A109.9C24B—C23B—H23C109.5
C7—C8—H8A109.9O17—C23B—H23D109.5
O6—C8—H8AB109.9C24B—C23B—H23D109.5
C7—C8—H8AB109.9H23C—C23B—H23D108.1
H8A—C8—H8AB108.3O18A—C25A—C26112.8 (12)
O6—C9—C10109.2 (7)O18A—C25A—H25A109.0
O6—C9—H9A109.8C26—C25A—H25A109.0
C10—C9—H9A109.8O18A—C25A—H25B109.0
O6—C9—H9AB109.8C26—C25A—H25B109.0
C10—C9—H9AB109.8H25A—C25A—H25B107.8
H9A—C9—H9AB108.3O18B—C25B—C2690.5 (12)
O7—C10—C9109.3 (6)O18B—C25B—H25C113.6
O7—C10—H10A109.8C26—C25B—H25C113.6
C9—C10—H10A109.8O18B—C25B—H25D113.6
O7—C10—H10B109.8C26—C25B—H25D113.6
C9—C10—H10B109.8H25C—C25B—H25D110.8
H10A—C10—H10B108.3O13—C26—C25B106.3 (14)
O7—C11—C12109.4 (7)O13—C26—C25A106.9 (12)
O7—C11—H11A109.8O13—C26—H26A110.3
C12—C11—H11A109.8C25A—C26—H26A110.3
O7—C11—H11B109.8O13—C26—H26B110.3
C12—C11—H11B109.8C25A—C26—H26B110.3
H11A—C11—H11B108.2H26A—C26—H26B108.6
O2—C12—C11107.1 (6)O13—C26—H26C110.5
O2—C12—H12A110.3C25B—C26—H26C110.5
C11—C12—H12A110.3O13—C26—H26D110.5
O2—C12—H12B110.3C25B—C26—H26D110.5
C11—C12—H12B110.3H26C—C26—H26D108.7
H12A—C12—H12B108.5F8—C27—F9109.0 (7)
F3—C13—F2109.3 (7)F8—C27—F7106.4 (8)
F3—C13—F1107.0 (8)F9—C27—F7106.1 (8)
F2—C13—F1107.3 (9)F8—C27—S3113.9 (6)
F3—C13—S1111.0 (7)F9—C27—S3111.6 (6)
F2—C13—S1110.2 (6)F7—C27—S3109.5 (5)
F1—C13—S1111.8 (6)F11—C28—F10109.1 (7)
F4—C14—F5107.5 (6)F11—C28—F12108.8 (6)
F4—C14—F6107.4 (6)F10—C28—F12109.3 (6)
F5—C14—F6102.9 (6)F11—C28—S4111.0 (5)
F4—C14—S2117.6 (6)F10—C28—S4108.7 (5)
F5—C14—S2109.5 (5)F12—C28—S4109.9 (6)
F6—C14—S2111.0 (4)H12C—O12—H12D101 (5)
H1C—O1—H1D93 (4)H12C—O12—H12E103 (5)
H1C—O1—H1E108 (5)H12D—O12—H12E110 (5)
H1D—O1—H1E97 (4)C26—O13—C15109.0 (9)
C1—O2—C12112.9 (6)C17—O14—C16113.0 (8)
C2—O3—C3111.4 (6)C18—O15—C19112.1 (7)
C4—O4—C5111.2 (7)C21—O16—C20111.7 (6)
C7—O5—C6114.3 (7)C22—O17—C23A118.1 (9)
C9—O6—C8114.0 (7)C22—O17—C23B106.2 (8)
C11—O7—C10110.0 (6)O18A—C24A—C23A109.3 (10)
S2—N1—S1125.7 (4)O18A—C24A—H24A109.8
O8—S1—O9118.5 (3)C23A—C24A—H24A109.8
O8—S1—N1108.3 (4)O18A—C24A—H24B109.8
O9—S1—N1115.5 (3)C23A—C24A—H24B109.8
O8—S1—C13103.9 (4)H24A—C24A—H24B108.3
O9—S1—C13104.9 (4)C24A—O18A—C25A126.5 (11)
N1—S1—C13104.1 (4)O18B—C24B—C23B106.5 (11)
O10—S2—O11118.7 (3)O18B—C24B—H24C110.4
O10—S2—N1108.7 (3)C23B—C24B—H24C110.4
O11—S2—N1116.5 (3)O18B—C24B—H24D110.4
O10—S2—C14102.1 (3)C23B—C24B—H24D110.4
O11—S2—C14106.7 (4)H24C—C24B—H24D108.6
N1—S2—C14101.7 (3)C24B—O18B—C25B101.0 (11)
O13—C15—C16108.4 (10)S4—N2—S3125.1 (4)
O13—C15—H15A110.0O19—S3—O20118.7 (3)
C16—C15—H15A110.0O19—S3—N2116.9 (3)
O13—C15—H15B110.0O20—S3—N2108.6 (3)
C16—C15—H15B110.0O19—S3—C27104.5 (4)
H15A—C15—H15B108.4O20—S3—C27103.9 (4)
O14—C16—C15108.1 (9)N2—S3—C27101.8 (3)
O14—C16—H16A110.1O21—S4—O22118.8 (3)
C15—C16—H16A110.1O21—S4—N2117.0 (3)
O14—C16—H16B110.1O22—S4—N2107.8 (3)
C15—C16—H16B110.1O21—S4—C28104.3 (3)
H16A—C16—H16B108.4O22—S4—C28104.0 (3)
O14—C17—C18107.8 (8)N2—S4—C28102.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1C···O51.00 (3)1.90 (6)2.690 (7)134 (6)
O1—H1C···O61.00 (3)2.08 (6)2.898 (8)138 (6)
O1—H1D···O21.01 (3)2.19 (7)2.835 (7)120 (5)
O1—H1D···O71.01 (3)1.96 (7)2.687 (7)127 (6)
O1—H1E···F5i1.03 (3)2.14 (6)2.989 (7)139 (6)
O1—H1E···F6i1.03 (3)2.12 (4)3.065 (7)152 (6)
O12—H12C···F11ii1.00 (3)2.50 (4)3.436 (8)154 (7)
O12—H12D···O130.97 (3)1.85 (6)2.666 (9)140 (7)
O12—H12D···O18A0.97 (3)2.36 (6)3.079 (12)131 (6)
O12—H12D···O18B0.97 (3)1.97 (6)2.753 (15)137 (7)
O12—H12E···O140.97 (3)2.14 (7)2.831 (8)128 (6)
O12—H12E···O150.97 (3)1.95 (6)2.718 (7)135 (6)
Symmetry codes: (i) x, y, z1; (ii) x, y, z+1.
 

Funding information

This work was supported financially by Grants-in-Aid for Scientific Research (B) (No. 19H02490: AK) from the Japan Society for the Promotion of Science (JSPS).

References

First citationHigashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationKitada, A., Takeoka, S., Kintsu, K., Fukami, K., Saimura, M., Nagata, T., Katahira, M. & Murase, K. (2018). J. Electrochem. Soc. 165, H121–H127.  Web of Science CrossRef CAS Google Scholar
First citationRigaku (2006). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar

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