organic compounds
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
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 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 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).
Keywords: crystal structure; hydronium; crown ether; complex cation; ionic liquid.
CCDC reference: 1982024
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). The title compound crystallizes in the monoclinic P21. The contains two crystallographically independent ion-pairs (Fig. 1); each 18-crown-6 molecule complexes with a hydronium ion. One of the 18-crown-6 molecules exhibits 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). 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). 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].
Synthesis and crystallization
The polycrystalline title compound was synthesized according to a previous report (Kitada et al., 2018). 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 . The structure was refined as an 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.
details are summarized in Table 2
|
Structural data
CCDC reference: 1982024
https://doi.org/10.1107/S2414314620001625/is4042sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314620001625/is4042Isup2.hkl
Data collection: RAPID-AUTO (Rigaku, 2006); cell
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).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) Å3 | Block, colorless |
Z = 4 | 0.50 × 0.30 × 0.20 mm |
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 on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H 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 = 1.10 | 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) |
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. |
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) |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
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···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. |
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
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Kitada, 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
Rigaku (2006). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.