Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616010676/qs3057sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229616010676/qs3057Isup2.hkl | |
MDL mol file https://doi.org/10.1107/S2053229616010676/qs3057Isup3.mol |
CCDC reference: 1489496
Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
C54H90N6O18·[Mg(H2O)6](CF3O3S)2·3H2O | Dx = 1.284 Mg m−3 |
Mr = 1595.91 | Mo Kα radiation, λ = 0.71073 Å |
Trigonal, P3 | Cell parameters from 9973 reflections |
a = 16.4188 (5) Å | θ = 2.5–31.5° |
c = 8.8395 (3) Å | µ = 0.16 mm−1 |
V = 2063.67 (14) Å3 | T = 100 K |
Z = 1 | Prism, colourless |
F(000) = 848 | 0.66 × 0.46 × 0.24 mm |
Bruker APEXII CCD diffractometer | 8681 independent reflections |
Radiation source: fine-focus sealed tube | 7479 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
Detector resolution: 512 pixels mm-1 | θmax = 31.5°, θmin = 1.4° |
φ and ω scans | h = −23→19 |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | k = −23→24 |
Tmin = 0.642, Tmax = 0.746 | l = −12→12 |
19702 measured 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)] = 0.047 | w = 1/[σ2(Fo2) + (0.0586P)2 + 0.5419P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.120 | (Δ/σ)max = 0.006 |
S = 1.04 | Δρmax = 0.42 e Å−3 |
8681 reflections | Δρmin = −0.28 e Å−3 |
324 parameters | Absolute structure: Flack x determined using 3081 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013); Hooft y determined using 4154 Bijvoet pairs (Hooft et al., 2008) |
10 restraints | Absolute structure parameter: 0.08 (4) |
Experimental. SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1337 before and 0.0601 after correction. The Ratio of minimum to maximum transmission is 0.8598. The λ/2 correction factor is 0.00150. |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.6667 | 0.3333 | 0.66117 (12) | 0.0184 (2) | |
F1 | 0.60558 (17) | 0.35704 (17) | 0.9207 (2) | 0.0438 (5) | |
O1 | 0.69848 (16) | 0.43012 (16) | 0.6250 (3) | 0.0285 (5) | |
C1 | 0.6667 | 0.3333 | 0.8658 (6) | 0.0265 (10) | |
S2 | 1.0000 | 1.0000 | 0.30056 (11) | 0.01403 (19) | |
F2 | 0.91560 (14) | 0.93744 (14) | 0.0403 (2) | 0.0336 (4) | |
O2 | 0.93719 (14) | 1.03489 (14) | 0.3376 (2) | 0.0204 (4) | |
C2 | 1.0000 | 1.0000 | 0.0944 (5) | 0.0222 (9) | |
Mg1 | 0.3333 | 0.6667 | 0.44311 (17) | 0.0187 (3) | |
H4A | 0.2937 (14) | 0.5084 (13) | 0.587 (5) | 0.060 (10)* | |
H4B | 0.4026 (16) | 0.567 (2) | 0.559 (4) | 0.060 (10)* | |
O3 | 0.44327 (15) | 0.67964 (16) | 0.3086 (3) | 0.0282 (5) | |
H3A | 0.5057 (11) | 0.725 (2) | 0.333 (3) | 0.042* | |
H3B | 0.4351 (19) | 0.671 (3) | 0.2020 (16) | 0.042* | |
O4 | 0.34675 (16) | 0.57098 (16) | 0.5779 (3) | 0.0319 (5) | |
O5 | 0.39800 (13) | 0.41075 (14) | 0.6719 (2) | 0.0205 (4) | |
O6 | 0.40520 (14) | 0.34550 (14) | 0.4513 (2) | 0.0222 (4) | |
O7 | 0.50107 (16) | 0.56902 (15) | 0.4816 (3) | 0.0287 (5) | |
O8 | 0.67291 (13) | 0.73269 (13) | 0.2606 (2) | 0.0192 (4) | |
O9 | 0.59991 (15) | 0.82266 (16) | 0.4373 (3) | 0.0352 (6) | |
O10 | 0.72909 (15) | 0.73641 (14) | 0.4949 (2) | 0.0261 (5) | |
N1 | 0.61651 (16) | 0.53350 (16) | 0.4809 (3) | 0.0195 (4) | |
H1 | 0.6406 | 0.5019 | 0.5236 | 0.023* | |
N2 | 0.74635 (16) | 0.94657 (16) | 0.4611 (3) | 0.0186 (4) | |
H2 | 0.8033 | 0.9777 | 0.4228 | 0.022* | |
C3 | 0.36146 (19) | 0.34741 (19) | 0.5583 (3) | 0.0174 (5) | |
C4 | 0.49917 (19) | 0.4676 (2) | 0.6805 (3) | 0.0211 (5) | |
H4 | 0.5273 | 0.4264 | 0.6949 | 0.025* | |
C5 | 0.53817 (19) | 0.52612 (19) | 0.5368 (3) | 0.0204 (5) | |
C6 | 0.66311 (19) | 0.59238 (18) | 0.3489 (3) | 0.0185 (5) | |
H6 | 0.6192 | 0.5691 | 0.2606 | 0.022* | |
C7 | 0.69074 (19) | 0.69393 (19) | 0.3818 (3) | 0.0188 (5) | |
C8 | 0.71813 (19) | 0.83473 (18) | 0.2629 (3) | 0.0202 (5) | |
H8 | 0.7878 | 0.8625 | 0.2702 | 0.024* | |
C9 | 0.68318 (19) | 0.86665 (19) | 0.3973 (3) | 0.0210 (5) | |
C10 | 0.72384 (18) | 0.98310 (19) | 0.5948 (3) | 0.0173 (5) | |
H10 | 0.6964 | 0.9324 | 0.6731 | 0.021* | |
C11 | 0.8147 (2) | 1.0665 (2) | 0.6580 (3) | 0.0223 (5) | |
H11 | 0.8483 | 1.1113 | 0.5733 | 0.027* | |
C12 | 0.8787 (2) | 1.0314 (3) | 0.7201 (4) | 0.0329 (7) | |
H12A | 0.8472 | 0.9880 | 0.8043 | 0.049* | |
H12B | 0.9377 | 1.0850 | 0.7558 | 0.049* | |
H12C | 0.8922 | 0.9986 | 0.6399 | 0.049* | |
C13 | 0.7937 (2) | 1.1190 (2) | 0.7812 (4) | 0.0336 (7) | |
H13A | 0.7593 | 1.1476 | 0.7370 | 0.050* | |
H13B | 0.8530 | 1.1682 | 0.8247 | 0.050* | |
H13C | 0.7555 | 1.0747 | 0.8607 | 0.050* | |
C14 | 0.6938 (2) | 0.8632 (2) | 0.1151 (4) | 0.0301 (6) | |
H14A | 0.7150 | 0.8396 | 0.0309 | 0.045* | |
H14B | 0.7250 | 0.9320 | 0.1096 | 0.045* | |
H14C | 0.6255 | 0.8366 | 0.1087 | 0.045* | |
C15 | 0.75134 (19) | 0.58643 (18) | 0.3117 (3) | 0.0191 (5) | |
H15 | 0.7868 | 0.5952 | 0.4080 | 0.023* | |
C16 | 0.7239 (2) | 0.4894 (2) | 0.2484 (4) | 0.0280 (6) | |
H16A | 0.7806 | 0.4846 | 0.2343 | 0.042* | |
H16B | 0.6921 | 0.4806 | 0.1509 | 0.042* | |
H16C | 0.6814 | 0.4408 | 0.3194 | 0.042* | |
C17 | 0.8166 (2) | 0.6631 (2) | 0.2011 (3) | 0.0271 (6) | |
H17A | 0.8720 | 0.6570 | 0.1813 | 0.041* | |
H17B | 0.8364 | 0.7251 | 0.2451 | 0.041* | |
H17C | 0.7831 | 0.6564 | 0.1060 | 0.041* | |
C18 | 0.5194 (2) | 0.5312 (2) | 0.8198 (3) | 0.0296 (6) | |
H18 | 0.4914 | 0.5721 | 0.8010 | 0.035* | |
C19 | 0.6254 (2) | 0.5952 (3) | 0.8420 (4) | 0.0375 (7) | |
H19A | 0.6550 | 0.5566 | 0.8559 | 0.056* | |
H19B | 0.6368 | 0.6346 | 0.9316 | 0.056* | |
H19C | 0.6522 | 0.6353 | 0.7527 | 0.056* | |
C20 | 0.4742 (3) | 0.4738 (3) | 0.9613 (4) | 0.0430 (9) | |
H20A | 0.4061 | 0.4351 | 0.9459 | 0.064* | |
H20B | 0.4866 | 0.5163 | 1.0471 | 0.064* | |
H20C | 0.5006 | 0.4331 | 0.9823 | 0.064* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0195 (3) | 0.0195 (3) | 0.0164 (5) | 0.00973 (16) | 0.000 | 0.000 |
F1 | 0.0497 (14) | 0.0575 (14) | 0.0289 (10) | 0.0304 (12) | 0.0095 (9) | −0.0088 (9) |
O1 | 0.0300 (12) | 0.0229 (10) | 0.0316 (11) | 0.0126 (9) | −0.0047 (9) | 0.0055 (8) |
C1 | 0.0315 (16) | 0.0315 (16) | 0.016 (2) | 0.0158 (8) | 0.000 | 0.000 |
S2 | 0.0134 (3) | 0.0134 (3) | 0.0152 (4) | 0.00671 (14) | 0.000 | 0.000 |
F2 | 0.0307 (10) | 0.0400 (11) | 0.0225 (9) | 0.0120 (9) | −0.0100 (7) | −0.0052 (8) |
O2 | 0.0173 (9) | 0.0204 (9) | 0.0250 (9) | 0.0107 (8) | 0.0037 (7) | 0.0002 (7) |
C2 | 0.0248 (15) | 0.0248 (15) | 0.017 (2) | 0.0124 (7) | 0.000 | 0.000 |
Mg1 | 0.0130 (4) | 0.0130 (4) | 0.0301 (9) | 0.00652 (19) | 0.000 | 0.000 |
O3 | 0.0173 (9) | 0.0309 (11) | 0.0354 (11) | 0.0112 (9) | 0.0015 (8) | −0.0006 (9) |
O4 | 0.0283 (11) | 0.0263 (11) | 0.0436 (13) | 0.0156 (9) | −0.0039 (9) | 0.0054 (9) |
O5 | 0.0134 (8) | 0.0220 (9) | 0.0239 (9) | 0.0074 (7) | −0.0026 (7) | −0.0050 (7) |
O6 | 0.0174 (9) | 0.0208 (10) | 0.0261 (10) | 0.0078 (8) | 0.0010 (7) | −0.0023 (8) |
O7 | 0.0243 (10) | 0.0237 (11) | 0.0420 (12) | 0.0149 (9) | −0.0021 (9) | 0.0035 (9) |
O8 | 0.0184 (9) | 0.0117 (8) | 0.0250 (9) | 0.0056 (7) | −0.0027 (7) | −0.0009 (7) |
O9 | 0.0151 (10) | 0.0256 (11) | 0.0528 (14) | 0.0010 (9) | 0.0104 (9) | −0.0101 (10) |
O10 | 0.0284 (11) | 0.0183 (10) | 0.0266 (10) | 0.0080 (9) | −0.0070 (8) | −0.0060 (8) |
N1 | 0.0157 (10) | 0.0170 (11) | 0.0252 (11) | 0.0078 (9) | −0.0033 (8) | 0.0003 (8) |
N2 | 0.0130 (10) | 0.0139 (10) | 0.0280 (11) | 0.0059 (8) | 0.0052 (8) | 0.0003 (8) |
C3 | 0.0153 (11) | 0.0168 (11) | 0.0219 (12) | 0.0094 (9) | −0.0028 (9) | −0.0001 (9) |
C4 | 0.0126 (11) | 0.0237 (13) | 0.0245 (12) | 0.0071 (10) | −0.0034 (9) | −0.0015 (10) |
C5 | 0.0180 (12) | 0.0145 (12) | 0.0267 (13) | 0.0066 (10) | −0.0058 (10) | −0.0030 (9) |
C6 | 0.0189 (12) | 0.0129 (11) | 0.0206 (12) | 0.0056 (10) | −0.0079 (9) | −0.0026 (9) |
C7 | 0.0160 (12) | 0.0139 (11) | 0.0237 (12) | 0.0054 (9) | −0.0008 (9) | 0.0001 (9) |
C8 | 0.0170 (12) | 0.0106 (11) | 0.0294 (13) | 0.0042 (9) | 0.0023 (9) | 0.0000 (9) |
C9 | 0.0132 (11) | 0.0140 (12) | 0.0343 (14) | 0.0057 (10) | 0.0038 (10) | 0.0005 (9) |
C10 | 0.0159 (11) | 0.0158 (11) | 0.0215 (12) | 0.0090 (10) | 0.0027 (9) | 0.0023 (9) |
C11 | 0.0215 (13) | 0.0216 (13) | 0.0223 (13) | 0.0096 (11) | −0.0033 (9) | 0.0003 (10) |
C12 | 0.0295 (16) | 0.049 (2) | 0.0270 (14) | 0.0249 (15) | −0.0061 (12) | 0.0040 (13) |
C13 | 0.0300 (16) | 0.0324 (16) | 0.0358 (16) | 0.0137 (13) | −0.0094 (12) | −0.0139 (13) |
C14 | 0.0334 (16) | 0.0236 (14) | 0.0327 (15) | 0.0139 (13) | 0.0036 (12) | 0.0064 (11) |
C15 | 0.0213 (12) | 0.0170 (12) | 0.0191 (11) | 0.0096 (10) | −0.0019 (9) | −0.0023 (9) |
C16 | 0.0343 (16) | 0.0226 (14) | 0.0283 (14) | 0.0151 (12) | −0.0006 (12) | −0.0049 (11) |
C17 | 0.0266 (15) | 0.0256 (14) | 0.0282 (14) | 0.0124 (12) | 0.0042 (11) | 0.0047 (11) |
C18 | 0.0231 (14) | 0.0355 (16) | 0.0282 (14) | 0.0132 (13) | −0.0077 (11) | −0.0131 (12) |
C19 | 0.0256 (15) | 0.0432 (19) | 0.0356 (16) | 0.0111 (14) | −0.0109 (12) | −0.0128 (14) |
C20 | 0.0320 (17) | 0.064 (2) | 0.0268 (15) | 0.0199 (17) | −0.0032 (12) | −0.0098 (15) |
S1—O1i | 1.439 (2) | C4—C18 | 1.539 (4) |
S1—O1 | 1.439 (2) | C6—H6 | 1.0000 |
S1—O1ii | 1.439 (2) | C6—C7 | 1.521 (4) |
S1—C1 | 1.809 (5) | C6—C15 | 1.535 (4) |
F1—C1 | 1.336 (3) | C8—H8 | 1.0000 |
C1—F1ii | 1.336 (3) | C8—C9 | 1.522 (4) |
C1—F1i | 1.336 (3) | C8—C14 | 1.507 (4) |
S2—O2iii | 1.446 (2) | C10—C3vi | 1.525 (4) |
S2—O2iv | 1.446 (2) | C10—H10 | 1.0000 |
S2—O2 | 1.446 (2) | C10—C11 | 1.540 (4) |
S2—C2 | 1.822 (5) | C11—H11 | 1.0000 |
F2—C2 | 1.334 (2) | C11—C12 | 1.532 (4) |
C2—F2iv | 1.334 (2) | C11—C13 | 1.531 (4) |
C2—F2iii | 1.334 (2) | C12—H12A | 0.9800 |
Mg1—O3v | 2.082 (2) | C12—H12B | 0.9800 |
Mg1—O3vi | 2.082 (2) | C12—H12C | 0.9800 |
Mg1—O3 | 2.082 (2) | C13—H13A | 0.9800 |
Mg1—O4vi | 2.070 (2) | C13—H13B | 0.9800 |
Mg1—O4 | 2.070 (2) | C13—H13C | 0.9800 |
Mg1—O4v | 2.070 (2) | C14—H14A | 0.9800 |
O3—H3A | 0.944 (13) | C14—H14B | 0.9800 |
O3—H3B | 0.953 (13) | C14—H14C | 0.9800 |
O4—H4A | 0.962 (13) | C15—H15 | 1.0000 |
O4—H4B | 0.966 (10) | C15—C16 | 1.529 (4) |
O5—C3 | 1.351 (3) | C15—C17 | 1.530 (4) |
O5—C4 | 1.444 (3) | C16—H16A | 0.9800 |
O6—C3 | 1.197 (3) | C16—H16B | 0.9800 |
O7—C5 | 1.239 (3) | C16—H16C | 0.9800 |
O8—C7 | 1.351 (3) | C17—H17A | 0.9800 |
O8—C8 | 1.454 (3) | C17—H17B | 0.9800 |
O9—C9 | 1.236 (3) | C17—H17C | 0.9800 |
O10—C7 | 1.201 (3) | C18—H18 | 1.0000 |
N1—H1 | 0.8791 | C18—C19 | 1.531 (4) |
N1—C5 | 1.326 (4) | C18—C20 | 1.517 (5) |
N1—C6 | 1.463 (4) | C19—H19A | 0.9800 |
N2—H2 | 0.8790 | C19—H19B | 0.9800 |
N2—C9 | 1.325 (4) | C19—H19C | 0.9800 |
N2—C10 | 1.454 (3) | C20—H20A | 0.9800 |
C3—C10v | 1.525 (4) | C20—H20B | 0.9800 |
C4—H4 | 1.0000 | C20—H20C | 0.9800 |
C4—C5 | 1.527 (4) | ||
O1i—S1—O1ii | 115.20 (7) | O8—C8—C9 | 110.1 (2) |
O1i—S1—O1 | 115.20 (7) | O8—C8—C14 | 106.5 (2) |
O1ii—S1—O1 | 115.20 (7) | C9—C8—H8 | 109.6 |
O1i—S1—C1 | 102.85 (10) | C14—C8—H8 | 109.6 |
O1ii—S1—C1 | 102.85 (10) | C14—C8—C9 | 111.4 (2) |
O1—S1—C1 | 102.85 (10) | O9—C9—N2 | 123.1 (3) |
F1—C1—S1 | 111.3 (2) | O9—C9—C8 | 121.3 (3) |
F1i—C1—S1 | 111.3 (2) | N2—C9—C8 | 115.5 (2) |
F1ii—C1—S1 | 111.3 (2) | N2—C10—C3vi | 111.2 (2) |
F1i—C1—F1 | 107.6 (2) | N2—C10—H10 | 108.8 |
F1ii—C1—F1 | 107.6 (2) | N2—C10—C11 | 109.2 (2) |
F1ii—C1—F1i | 107.6 (2) | C3vi—C10—H10 | 108.8 |
O2iii—S2—O2 | 115.01 (7) | C3vi—C10—C11 | 110.1 (2) |
O2iv—S2—O2 | 115.01 (7) | C11—C10—H10 | 108.8 |
O2iii—S2—O2iv | 115.01 (7) | C10—C11—H11 | 108.4 |
O2iii—S2—C2 | 103.11 (9) | C12—C11—C10 | 109.7 (2) |
O2iv—S2—C2 | 103.11 (9) | C12—C11—H11 | 108.4 |
O2—S2—C2 | 103.11 (9) | C13—C11—C10 | 111.6 (2) |
F2iv—C2—S2 | 111.01 (19) | C13—C11—H11 | 108.4 |
F2iii—C2—S2 | 111.01 (19) | C13—C11—C12 | 110.3 (3) |
F2—C2—S2 | 111.01 (19) | C11—C12—H12A | 109.5 |
F2iii—C2—F2 | 107.9 (2) | C11—C12—H12B | 109.5 |
F2iii—C2—F2iv | 107.9 (2) | C11—C12—H12C | 109.5 |
F2iv—C2—F2 | 107.9 (2) | H12A—C12—H12B | 109.5 |
O3vi—Mg1—O3v | 90.60 (10) | H12A—C12—H12C | 109.5 |
O3v—Mg1—O3 | 90.60 (10) | H12B—C12—H12C | 109.5 |
O3vi—Mg1—O3 | 90.60 (10) | C11—C13—H13A | 109.5 |
O4v—Mg1—O3vi | 89.78 (9) | C11—C13—H13B | 109.5 |
O4vi—Mg1—O3v | 179.61 (11) | C11—C13—H13C | 109.5 |
O4vi—Mg1—O3 | 89.78 (9) | H13A—C13—H13B | 109.5 |
O4vi—Mg1—O3vi | 89.46 (10) | H13A—C13—H13C | 109.5 |
O4v—Mg1—O3 | 179.61 (11) | H13B—C13—H13C | 109.5 |
O4—Mg1—O3vi | 179.61 (12) | C8—C14—H14A | 109.5 |
O4—Mg1—O3 | 89.46 (10) | C8—C14—H14B | 109.5 |
O4v—Mg1—O3v | 89.46 (10) | C8—C14—H14C | 109.5 |
O4—Mg1—O3v | 89.78 (9) | H14A—C14—H14B | 109.5 |
O4vi—Mg1—O4 | 90.15 (11) | H14A—C14—H14C | 109.5 |
O4v—Mg1—O4vi | 90.15 (11) | H14B—C14—H14C | 109.5 |
O4v—Mg1—O4 | 90.15 (11) | C6—C15—H15 | 108.0 |
Mg1—O3—H3A | 119.3 (17) | C16—C15—C6 | 110.4 (2) |
Mg1—O3—H3B | 120.1 (17) | C16—C15—H15 | 108.0 |
H3A—O3—H3B | 112 (2) | C16—C15—C17 | 110.1 (2) |
Mg1—O4—H4A | 118 (2) | C17—C15—C6 | 112.3 (2) |
Mg1—O4—H4B | 114.4 (18) | C17—C15—H15 | 108.0 |
H4A—O4—H4B | 109.0 (19) | C15—C16—H16A | 109.5 |
C3—O5—C4 | 117.5 (2) | C15—C16—H16B | 109.5 |
C7—O8—C8 | 115.2 (2) | C15—C16—H16C | 109.5 |
C5—N1—H1 | 119.2 | H16A—C16—H16B | 109.5 |
C5—N1—C6 | 121.4 (2) | H16A—C16—H16C | 109.5 |
C6—N1—H1 | 119.4 | H16B—C16—H16C | 109.5 |
C9—N2—H2 | 119.3 | C15—C17—H17A | 109.5 |
C9—N2—C10 | 121.4 (2) | C15—C17—H17B | 109.5 |
C10—N2—H2 | 119.3 | C15—C17—H17C | 109.5 |
O5—C3—C10v | 109.2 (2) | H17A—C17—H17B | 109.5 |
O6—C3—O5 | 124.4 (2) | H17A—C17—H17C | 109.5 |
O6—C3—C10v | 126.3 (2) | H17B—C17—H17C | 109.5 |
O5—C4—H4 | 110.0 | C4—C18—H18 | 107.9 |
O5—C4—C5 | 110.3 (2) | C19—C18—C4 | 110.7 (2) |
O5—C4—C18 | 105.6 (2) | C19—C18—H18 | 107.9 |
C5—C4—H4 | 110.0 | C20—C18—C4 | 111.4 (3) |
C5—C4—C18 | 111.0 (2) | C20—C18—H18 | 107.9 |
C18—C4—H4 | 110.0 | C20—C18—C19 | 110.8 (3) |
O7—C5—N1 | 122.1 (3) | C18—C19—H19A | 109.5 |
O7—C5—C4 | 121.0 (3) | C18—C19—H19B | 109.5 |
N1—C5—C4 | 116.7 (2) | C18—C19—H19C | 109.5 |
N1—C6—H6 | 109.3 | H19A—C19—H19B | 109.5 |
N1—C6—C7 | 110.0 (2) | H19A—C19—H19C | 109.5 |
N1—C6—C15 | 109.1 (2) | H19B—C19—H19C | 109.5 |
C7—C6—H6 | 109.3 | C18—C20—H20A | 109.5 |
C7—C6—C15 | 109.7 (2) | C18—C20—H20B | 109.5 |
C15—C6—H6 | 109.3 | C18—C20—H20C | 109.5 |
O8—C7—C6 | 110.4 (2) | H20A—C20—H20B | 109.5 |
O10—C7—O8 | 124.1 (2) | H20A—C20—H20C | 109.5 |
O10—C7—C6 | 125.3 (2) | H20B—C20—H20C | 109.5 |
O8—C8—H8 | 109.6 | ||
O1i—S1—C1—F1ii | −56.91 (15) | N2—C10—C11—C13 | 169.9 (2) |
O1ii—S1—C1—F1i | −176.91 (15) | C3—O5—C4—C5 | 60.6 (3) |
O1i—S1—C1—F1 | −176.91 (15) | C3—O5—C4—C18 | −179.4 (2) |
O1ii—S1—C1—F1ii | 63.09 (15) | C3vi—C10—C11—C12 | 170.1 (2) |
O1—S1—C1—F1i | −56.91 (15) | C3vi—C10—C11—C13 | 47.5 (3) |
O1—S1—C1—F1ii | −176.91 (15) | C4—O5—C3—O6 | −12.8 (4) |
O1ii—S1—C1—F1 | −56.91 (15) | C4—O5—C3—C10v | 163.1 (2) |
O1i—S1—C1—F1i | 63.09 (15) | C5—N1—C6—C7 | 59.6 (3) |
O1—S1—C1—F1 | 63.09 (15) | C5—N1—C6—C15 | −180.0 (2) |
O2iii—S2—C2—F2iii | −66.20 (12) | C5—C4—C18—C19 | −60.7 (3) |
O2iv—S2—C2—F2iv | −66.20 (13) | C5—C4—C18—C20 | 175.4 (3) |
O2iv—S2—C2—F2 | 53.80 (12) | C6—N1—C5—O7 | −0.7 (4) |
O2iv—S2—C2—F2iii | 173.80 (12) | C6—N1—C5—C4 | −176.3 (2) |
O2iii—S2—C2—F2 | 173.80 (12) | C7—O8—C8—C9 | −62.2 (3) |
O2—S2—C2—F2iii | 53.80 (13) | C7—O8—C8—C14 | 176.8 (2) |
O2—S2—C2—F2 | −66.20 (12) | C7—C6—C15—C16 | −168.9 (2) |
O2iii—S2—C2—F2iv | 53.80 (13) | C7—C6—C15—C17 | −45.6 (3) |
O2—S2—C2—F2iv | 173.80 (13) | C8—O8—C7—O10 | 10.6 (4) |
O5—C4—C5—O7 | 45.2 (4) | C8—O8—C7—C6 | −164.6 (2) |
O5—C4—C5—N1 | −139.1 (2) | C9—N2—C10—C3vi | −67.9 (3) |
O5—C4—C18—C19 | 179.7 (3) | C9—N2—C10—C11 | 170.4 (2) |
O5—C4—C18—C20 | 55.9 (3) | C10—N2—C9—O9 | 6.7 (5) |
O8—C8—C9—O9 | −38.7 (4) | C10—N2—C9—C8 | −177.1 (2) |
O8—C8—C9—N2 | 145.1 (2) | C14—C8—C9—O9 | 79.3 (3) |
N1—C6—C7—O8 | −138.5 (2) | C14—C8—C9—N2 | −97.0 (3) |
N1—C6—C7—O10 | 46.4 (4) | C15—C6—C7—O8 | 101.5 (2) |
N1—C6—C15—C16 | 70.5 (3) | C15—C6—C7—O10 | −73.6 (3) |
N1—C6—C15—C17 | −166.2 (2) | C18—C4—C5—O7 | −71.5 (3) |
N2—C10—C11—C12 | −67.6 (3) | C18—C4—C5—N1 | 104.2 (3) |
Symmetry codes: (i) −x+y+1, −x+1, z; (ii) −y+1, x−y, z; (iii) −x+y+1, −x+2, z; (iv) −y+2, x−y+1, z; (v) −x+y, −x+1, z; (vi) −y+1, x−y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4A···O9v | 0.96 (1) | 2.05 (3) | 2.802 (3) | 134 (4) |
O4—H4B···O7 | 0.97 (1) | 1.74 (1) | 2.688 (3) | 167 (3) |
O3—H3A···O9 | 0.94 (1) | 1.82 (2) | 2.717 (3) | 157 (3) |
N1—H1···O1 | 0.88 | 2.05 | 2.933 (4) | 179 |
N2—H2···O2 | 0.88 | 2.05 | 2.927 (4) | 173 |
Symmetry code: (v) −x+y, −x+1, z. |