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TRANSCRIPT
Comprehensive study on the impact of the cation alkyl side chain
length on the solubility of water in ionic liquids
Kiki A. Kurnia,1 Catarina M. S. S. Neves,1 Mara G. Freire,1 Luís M. N. B. F. Santos,2 and João A.
P. Coutinho1,*
1 Departamento de Química, CICECO, Universidade de Aveiro, 3810-193 Aveiro, Portugal.
2 Centro de Investigação em Química, Departamento de Química e Bioquímica, Faculdade de
Ciências da Universidade do Porto, R. Campo Alegre 687, P-4169-007 Porto, Portugal.
Supplementary data
*Corresponding Author: Tel.:+351 234 370200; Fax: +351 234 370084; E-mail: [email protected]
(J.A.P. Coutinho).
Figure S1. Logarithm of mole fraction solubility of water, xw, as function of (1/T) in the studied
ILs. Symbols: (♦,─), [C6C6im][NTf2]; (■,─), [C7C7im][NTf2]; (▲,─), [C8C8im][NTf2]; (●,─),
[C9C9im][NTf2]; (◊,---), [C9C1im][NTf2]; (□,---), [C10C1im][NTf2]; and (∆,---), [C11C1im][NTf2]. The
symbols and lines represent experimental and the correlation of the experimental data using
Equation (1).
Figure S2. Solubility of water in ILs, xw, at T = 313.15 K and p = 0.1 MPa as function of the total
number of carbon atoms at the alkyl chains, N: (♦) symmetric ILs and (■) asymmetric ILs. The lines
are only presented to facilitate the reading and to better follow the trend shifts.
Figure S3. Solubility of water in ILs, xw, at T = 318.15 K and p = 0.1 MPa as function of the total
number of carbon atoms at the alkyl chains, N: (♦) symmetric ILs and (■) asymmetric ILs. The lines
are only presented to facilitate the reading and to better follow the trend shifts.
Figure S4. COSMO-RS prediction of solubility of water in ILs, xw, at T = 308.15 K and p = 0.1
MPa as function of the total number of carbon atoms at the alkyl chains, N: (♦) symmetric ILs and
(■) asymmetric ILs.
Figure S5. Sigma profile (a) and potential (b) of water estimated using COSMO-RS at BP_TZVP
level.
Table S1. Mole fraction solubility of water (xw) in ILs and ILs in water (xIL) as function of
temperature and at 0.1 MPa predicted using COSMO-RS at BP_TZVP_C20_0111 parameter file
T/K xw xIL
[C6C6im][NTf2]288.15 0.1500 2.29 × 10-5
293.15 0.1631 2.30 × 10-5
298.15 0.1770 2.33 × 10-5
303.15 0.1915 2.38 × 10-5
308.15 0.2068 2.46 × 10-5
313.15 0.2229 2.57 × 10-5
318.15 0.2397 2.69 × 10-5
[C7C7im][NTf2]288.15 0.1344 7.41 × 10-6
293.15 0.1461 7.46 × 10-6
298.15 0.1589 7.61 × 10-6
303.15 0.1726 7.48 × 10-6
308.15 0.1872 8.12 × 10-6
313.15 0.2023 8.48 × 10-6
318.15 0.2181 8.96 × 10-6
[C8C8im][NTf2]288.15 0.1222 2.51 × 10-6
293.15 0.1333 2.54 × 10-6
298.15 0.1452 2.59 × 10-6
303.15 0.1581 2.68 × 10-6
308.15 0.1717 2.79 × 10-6
313.15 0.1857 2.94 × 10-6
318.15 0.2008 3.12 × 10-6
[C9C9im][NTf2]288.15 0.1116 8.01 × 10-7
293.15 0.1222 8.10 × 10-7
298.15 0.1335 8.29 × 10-7
303.15 0.1455 8.60 × 10-7
308.15 0.1584 9.01 × 10-7
313.15 0.1720 9.60 × 10-7
318.15 0.1861 1.02 × 10-6
[C10C10im][NTf2]288.15 0.1027 2.50 × 10-7
293.15 0.1125 2.60 × 10-7
298.15 0.1232 2.69 × 10-7
303.15 0.1346 2.81 × 10-7
308.15 0.1467 2.91 × 10-7
313.15 0.1597 3.11 × 10-7
318.15 0.1734 3.40 × 10-7
[C11C11im][NTf2]288.15 0.0943 8.01 × 10-8
293.15 0.1038 8.28 × 10-8
298.15 0.1138 8.71 × 10-8
303.15 0.1246 9.00 × 10-8
308.15 0.1362 9.51 × 10-8
313.15 0.1485 1.01 × 10-7
318.15 0.1616 1.10 × 10-7
[C9C1im][NTf2]288.15 0.1740 6.95 × 10-5
293.15 0.1881 6.99 × 10-5
298.15 0.2037 7.11 × 10-5
303.15 0.2199 7.27 × 10-5
308.15 0.2370 7.50 × 10-5
313.15 0.2551 7.79 × 10-5
318.15 0.2735 8.15 × 10-5
[C10C1im][NTf2]288.15 0.1619 3.93 × 10-5
293.15 0.1758 3.95 × 10-5
298.15 0.1904 4.01 × 10-5
303.15 0.2059 4.11 × 10-5
308.15 0.2217 4.23 × 10-5
313.15 0.2388 4.40 × 10-5
318.15 0.2569 4.61 × 10-5
[C11C1im][NTf2]288.15 0.1546 2.31 × 10-5
293.15 0.1678 2.33 × 10-5
298.15 0.1818 2.37 × 10-5
303.15 0.1973 2.43 × 10-5
308.15 0.2132 2.51 × 10-5
313.15 0.2298 2.62 × 10-5
318.15 0.2470 2.76 × 10-5
Table S2. Atom coordinates, electrostatic potential-derived CHelpG charges, and sigma moment for
water calculated at the BP_TZVP level of theory.
Centre Number
Atomic Number Atom Coordinate/Å CHelpG HB_acc3 HB_don3X Y X
1 1 H 0.6391 -0.0279 0.4947 0.3952 0 1.92552 8 O 0.1598 0.0324 -0.3698 -0.7904 5.6933 03 1 H -0.7990 -0.0045 -0.1249 0.3952 0 1.9252
Table S3. Atom coordinates, electrostatic potential-derived CHelpG charges, and sigma moment for
[NTf2]- calculated at the BP_TZVP level of theory.
Centre Number
Atomic Number Atom Coordinate/Å CHelpG HB_acc3 HB_don3X Y X
1 6 C -0.3638 -0.0445 2.6363 0.3708 0 02 9 F -1.4434 -0.7669 2.2879 -0.1098 0 03 16 S 0.8690 0.0948 1.1568 0.8521 0 04 8 O 1.8978 1.0554 1.6514 -0.5000 0.5086 05 7 N -0.0011 0.8858 0.0003 -0.6267 0.6511 06 16 S -0.8696 0.0948 -1.1573 0.8556 0 07 8 O -1.2738 -1.3118 -0.8670 -0.4981 0.2948 08 8 O 1.2734 -1.3116 0.8663 -0.4972 0.3072 09 9 F 0.2600 -0.6546 3.6631 -0.1620 0 010 9 F -0.7620 1.1790 3.0295 -0.1412 0 011 6 C 0.3643 -0.0445 -2.6359 0.3707 0 012 9 F 1.4455 -0.7635 -2.2855 -0.1097 0 013 8 O -1.8983 1.0550 -1.6525 -0.5010 0.5305 014 9 F -0.2575 -0.6581 -3.6618 -0.1622 0 015 9 F 0.7596 1.1792 -3.0314 -0.1414 0 0
Table S4. Atom coordinates, electrostatic potential-derived CHelpG charges, and sigma moment for
[C1C1im]+ cation calculated at the BP_TZVP level of theory.
Centre Number
Atomic Numbe
rAtom
Coordinate/ÅCHelpG HB_acc3 HB_don3X Y X
1 7 N -0.6396 -0.8234 -0.0533 0.1457 0 02 6 C 0.6958 -0.9957 -0.0881 -0.0458 0 03 7 N 1.3262 0.1737 -0.3108 0.1457 0 04 6 C 0.3632 1.1106 -0.4196 -0.1350 0 05 6 C -0.8594 0.4906 -0.2595 -0.1350 0 06 6 C 2.7657 0.3766 -0.4124 -0.1767 0 07 6 C -1.6416 -1.8587 0.1649 -0.1767 0 08 1 H -1.4769 -2.3351 1.1541 0.1246 0 09 1 H -1.5615 -2.6292 -0.6305 0.1246 0 0.014610 1 H -2.6637 -1.4238 0.1416 0.1415 0 011 1 H 2.9967 1.4470 -0.5998 0.1415 0 012 1 H 3.1699 -0.2296 -1.2502 0.1246 0 0.023613 1 H 3.2544 0.0646 0.5344 0.1246 0 014 1 H 1.1959 -1.9473 0.0450 0.2020 0 0.257415 1 H -1.8336 0.9612 -0.2909 0.2020 0 0.254216 1 H 0.5368 2.1634 -0.6014 0.1923 0 1.4407
Table S5. Atom coordinates, electrostatic potential-derived CHelpG charges, and sigma moment for
[C2C1im]+ cation calculated at the BP_TZVP level of theory.
Centre Number
Atomic Numbe
rAtom
Coordinate/ÅCHelpG HB_acc3 HB_don3X Y X
1 6 C 0.4610 -0.9873 -0.1202 -0.1325 0 0
2 7 N 1.5868 -0.0974 0.0452 0.1723 0 0
3 6 C 1.1380 1.2354 -0.0172 -0.1220 0 0
4 6 C -0.2179 1.2356 -0.2130 -0.1351 0 0
5 7 N -0.6681 -0.0992 -0.2781 0.0592 0 0
6 6 C 2.9564 -0.5035 0.2411 -0.2198 0 0
7 6 C -2.0369 -0.5178 -0.4882 0.0903 0 0
8 6 C -2.9324 -0.0348 0.6483 -0.0947 0 0
9 1 H -3.9743 -0.3757 0.4721 0.0769 0 0
10 1 H 1.7678 2.1107 0.0734 0.2109 0 0.2577
11 1 H -0.8454 2.1123 -0.3050 0.2286 0 0.2366
12 1 H 0.4628 -2.0974 -0.1252 0.2565 0 1.4627
13 1 H -2.0887 -1.6275 -0.5329 0.0641 0 0.0066
14 1 H -2.4035 -0.1099 -1.4545 0.0554 0 0
15 1 H -2.9281 1.0740 0.7046 0.0394 0 0
16 1 H -2.5774 -0.4506 1.6152 0.0439 0 0
17 1 H 3.5852 -0.1047 -0.5824 0.1330 0 0
18 1 H 3.0347 -1.6114 0.2496 0.1375 0 0.0172
19 1 H 3.3274 -0.1092 1.2102 0.1361 0 0
Table S6. Atom coordinates, electrostatic potential-derived CHelpG charges, and sigma moment for
[C3C1im]+ cation calculated at the BP_TZVP level of theory.
Centre Number
Atomic Numbe
rAtom
Coordinate/ÅCHelpG HB_acc3 HB_don3X Y X
1 6 C 0.9480 -0.9701 -0.1609 -0.1231 0 0
2 7 N 2.1095 -0.1436 0.0720 0.1396 0 0
36 C 1.7306 1.2115 0.0316 -0.0973 0 0
4 6 C 0.3850 1.2861 -0.2144 -0.1760 0 0
5 7 N -0.1285 -0.0217 -0.3349 0.1226 0 0
6 6 C 3.4486 -0.6242 0.3068 -0.1970 0 0
7 6 C -1.5075 -0.3642 -0.6077 -0.1396 0 0
8 6 C -2.4219 0.1356 0.5159 0.2573 0 0
9 6 C -3.8780 -0.2314 0.2457 -0.2232 0 0
10 1 H 2.3994 2.0507 0.1709 0.2063 0 0.2416
11 1 H -0.1938 2.1959 -0.3043 0.2368 0 0.2368
12 1 H 0.8946 -2.0784 -0.1979 0.2535 0 1.4463
13 1 H -1.6061 -1.4691 -0.6902 0.1046 0 0
14 1 H -1.8100 0.0885 -1.5769 0.1039 0 0.0032
15 1 H -2.3433 1.2405 0.6040 -0.0344 0 0
16 1 H -2.1063 -0.3221 1.4787 -0.0339 0 0
17 1 H 4.1278 -0.2359 -0.4807 0.1297 0 0
18 1 H 3.4711 -1.7345 0.2861 0.1331 0 0.0158
19 1 H 3.8011 -0.2758 1.3002 0.1294 0 0
20 1 H -4.2228 0.2320 -0.7033 0.0626 0 0
21 1 H -4.5157 0.1403 1.0752 0.0823 0 0
22 1 H -3.9922 -1.3342 0.1762 0.0629 0 0
Table S7. Atom coordinates, electrostatic potential-derived CHelpG charges, and sigma moment for
[C4C1im]+ cation calculated at the BP_TZVP level of theory.
Centre Number
Atomic Numbe
rAtom
Coordinate/ÅCHelpG HB_acc3 HB_don3X Y X
1 6 C 1.5038 -0.9812 -0.0962 -0.1577 0 0
2 7 N 2.6194 -0.1064 0.1806 0.1357 0 0
36 C 2.2175 1.2303 -0.0023 -0.0996 0 0
4 6 C 0.9009 1.2473 -0.3804 -0.2088 0 0
5 7 N 0.4294 -0.0800 -0.4458 0.2167 0 0
6 6 C 3.9391 -0.5290 0.5791 -0.1694 0 0
7 6 C -0.9091 -0.4819 -0.8206 -0.2188 0 0
8 6 C -1.9388 0.0751 0.1686 0.1246 0 0
9 6 C -3.3587 -0.3576 -0.2139 0.1783 0 0
10 1 H 2.8517 2.0965 0.1335 0.2086 0 0.2411
11 1 H 0.3145 2.1307 -0.5963 0.2484 0 0.2355
12 1 H 1.4776 -2.0901 -0.0504 0.2638 0 1.439
13 1 H -0.9754 -1.5922 -0.8252 0.1116 0 0
14 1 H -1.1258 -0.1132 -1.8466 0.1103 0 0.0032
15 1 H -1.8852 1.1856 0.1744 -0.0160 0 0
16 1 H -1.7000 -0.2996 1.1884 -0.0124 0 0
17 1 H 4.6834 -0.1826 -0.1682 0.1224 0 0.0166
18 1 H 3.9870 -1.6365 0.6481 0.1256 0 0
19 1 H 4.1859 -0.0958 1.5710 0.1223 0 0
20 1 H -3.6016 0.0168 -1.2323 -0.0178 0 0
21 6 C -4.3862 0.1921 0.7712 -0.2750 0 0
22 1 H -3.4234 -1.4677 -0.2169 -0.0187 0 0
23 1 H -4.3587 1.3027 0.7783 0.0685 0 0
24 1 H -4.1793 -0.1848 1.7955 0.0697 0 0
25 1 H -5.4033 -0.1363 0.4702 0.0878 0 0
Table S8. Atom coordinates, electrostatic potential-derived CHelpG charges, and sigma moment for
[C5C1im]+ cation calculated at the BP_TZVP level of theory.
Centre Number
Atomic Numbe
rAtom
Coordinate/ÅCHelpG HB_acc3 HB_don3X Y X
1 6 C 2.0542 -0.9842 -0.1106 -0.1593 0 0
2 7 N 3.1770 -0.1330 0.2078 0.1510 0 0
3 6 C 2.7993 1.2133 0.0463 -0.0910 0 0
4 6 C 1.4911 1.2591 -0.3577 -0.2052 0 0
57 N 1.0010 -0.0590 -0.4618 0.1638 0 0
6 6 C 4.4818 -0.5847 0.6235 -0.1957 0 0
7 6 C -0.3355 -0.4317 -0.8720 -0.0701 0 0
8 6 C -1.3766 0.1197 0.1086 0.1106 0 0
9 6 C -2.7953 -0.2823 -0.3110 -0.0277 0 0
10 1 H 3.4436 2.0665 0.2140 0.2034 0 0.256
11 1 H 0.9227 2.1559 -0.5659 0.2480 0 0.2324
12 1 H 2.0103 -2.0932 -0.0896 0.2641 0 1.4327
13 1 H -0.4185 -1.5406 -0.9024 0.0783 0 0
14 1 H -0.5257 -0.0376 -1.8938 0.0756 0 0.0037
15 1 H -1.3061 1.2287 0.1397 -0.0230 0 0
16 1 H -1.1638 -0.2807 1.1243 -0.0186 0 0.0119
17 1 H 5.2464 -0.2338 -0.1008 0.1269 0 0
18 1 H 4.5115 -1.6941 0.6691 0.1321 0 0
19 1 H 4.7147 -0.1770 1.6295 0.1284 0 0
20 1 H -3.0043 0.1180 -1.3277 0.0224 0 0
21 6 C -3.8352 0.2665 0.6725 0.1240 0 0
22 1 H -2.8690 -1.3920 -0.3411 0.0206 0 0
23 1 H -3.7700 1.3761 0.7050 -0.0103 0 0
24 1 H -3.6340 -0.1326 1.6906 -0.0093 0
25 6 C -5.2490 -0.1314 0.2586 -0.2108 0 0
26 1 H -5.4851 0.2741 -0.7484 0.0527 0 0
27 1 H -5.9796 0.2788 0.9872 0.0670 0 0
28 1 H -5.3488 -1.2376 0.2393 0.0524 0 0
Table S9. Atom coordinates, electrostatic potential-derived CHelpG charges, and sigma moment for
[C6C1im]+ cation calculated at the BP_TZVP level of theory.
Centre Number
Atomic Numbe
rAtom
Coordinate/ÅCHelpG HB_acc3 HB_don3X Y X
1 6 C 2.6365 -0.9694 0.0937 -0.1466 0 0
2 7 N 3.7217 -0.0429 0.3181 0.1385 0 0
3 6 C 3.3263 1.2436 -0.0943 -0.0852 0 0
46 C 2.0427 1.1798 -0.5685 -0.2110 0 0
5 7 N 1.5864 -0.1507 -0.4679 0.1675 0 0
6 6 C 5.0096 -0.3769 0.8739 -0.1851 0 0
7 6 C 0.2834 -0.6284 -0.8771 -0.1537 0 0
8 6 C -0.8231 0.0522 -0.0636 0.2145 0 0
9 6 C -2.2070 -0.4584 -0.4816 -0.0400 0 0
10 1 H 3.9424 2.1318 -0.0437 0.2025 0 0.2558
11 1 H 1.4688 2.0099 -0.9589 0.2505 0 0.2292
12 1 H 2.6142 -2.0592 0.3044 0.2611 0 1.4147
13 1 H 0.2250 -1.7279 -0.7188 0.0984 0 0
14 1 H 0.1440 -0.4220 -1.9604 0.0995 0 0.0029
15 1 H -0.7770 1.1516 -0.2218 -0.0416 0 0
16 1 H -0.6608 -0.1608 1.0160 -0.0349 0 0
17 1 H 5.8069 -0.1332 0.1408 0.1258 0 0.0144
18 1 H 5.0594 -1.4604 1.1128 0.1292 0 0
19 1 H 5.1765 0.2047 1.8046 0.1258 0 0
20 1 H -2.3652 -0.2457 -1.5620 0.0130 0 0
21 6 C -3.3133 0.2200 0.3350 -0.0607 0 0
22 1 H -2.2560 -1.5584 -0.3224 0.0124 0 0
23 1 H -3.2649 1.3200 0.1760 0.0223 0 0
24 1 H -3.1549 0.0072 1.4154 0.0223 0 0
25 6 C -4.6969 -0.2907 -0.0833 0.1907 0 0
26 1 H -4.8636 -0.0780 -1.1618 -0.0266 0 0
27 6 C -5.8008 0.3821 0.7274 -0.2250 0 0
28 1 H -4.7537 -1.3897 0.0766 -0.0275 0 0
29 1 H -5.7811 1.4815 0.5686 0.0512 0 0
30 1 H -5.6710 0.1671 1.8095 0.0515 0 0
31 1 H -6.7896 -0.0061 0.4039 0.0612 0 0
Table S10. Atom coordinates, electrostatic potential-derived CHelpG charges, and sigma moment
for [C7C1im]+ cation calculated at the BP_TZVP level of theory.
Centre Number
Atomic Number Atom
Coordinate/ÅCHelpG HB_acc3 HB_don3
X Y X
1 6 C 3.2124 -0.9771 0.0864 -0.1533 0 0
2 7 N 4.3007 -0.0618 0.3397 0.1309 0 0
3 6 C 3.9176 1.2347 -0.0525 -0.0776 0 0
46 C 2.6387 1.1878 -0.5413 -0.2187 0 0
5 7 N 2.1733 -0.1414 -0.4706 0.1925 0 0
6 6 C 5.5805 -0.4142 0.9028 -0.1836 0 0
7 6 C 0.8718 -0.6032 -0.9023 -0.1741 0 0
8 6 C -0.2390 0.0689 -0.0876 0.1620 0 0
9 6 C -1.6215 -0.4251 -0.5292 0.0905 0 0
10 1 H 4.5384 2.1179 0.0214 0.2005 0 0.2362
11 1 H 2.0740 2.0287 -0.9220 0.2515 0 0.2501
12 1 H 3.1812 -2.0705 0.2764 0.2632 0 1.4391
13 1 H 0.8050 -1.7050 -0.7654 0.1009 0 0
14 1 H 0.7449 -0.3756 -1.9829 0.1006 0 0.0043
15 1 H -0.1847 1.1708 -0.2245 -0.0302 0 0
16 1 H -0.0892 -0.1653 0.9895 -0.0241 0 0
17 1 H 6.3871 -0.1618 0.1830 0.1257 0 0.0153
18 1 H 5.6211 -1.5023 1.1218 0.1300 0 0
19 1 H 5.7408 0.1488 1.8461 0.1257 0 0
20 1 H -1.7673 -0.1912 -1.6070 -0.0090 0 0
21 6 C -2.7321 0.2447 0.2888 -0.1291 0 0
22 1 H -1.6787 -1.5276 -0.3914 -0.0114 0 0
23 1 H -2.6752 1.3471 0.1510 0.0274 0 0
24 1 H -2.5857 0.0107 1.3665 0.0270 0 0
25 6 C -4.1149 -0.2493 -0.1525 0.0302 0
26 1 H -4.2616 -0.0152 -1.2301 0.0019 0 0
27 6 C -5.2247 0.4207 0.6659 0.1759 0 0
28 1 H -4.1721 -1.3517 -0.0146 0.0026 0 0
29 1 H -5.1759 1.5232 0.5299 -0.0293 0 0
30 1 H -5.0863 0.1878 1.7444 -0.0290 0 0
31 6 C -6.6027 -0.0685 0.2298 -0.2286 0 0
32 1 H -6.7767 0.1716 -0.8408 0.0495 0 0
33 1 H -7.3852 0.4323 0.8381 0.0604 0 0
34 1 H -6.6869 -1.1664 0.3762 0.0491 0 0
Table S11. Atom coordinates, electrostatic potential-derived CHelpG charges, and sigma moment
for [C8C1im]+ cation calculated at the BP_TZVP level of theory.
Centre Number
Atomic Numbe
rAtom
Coordinate/ÅCHelpG HB_acc3 HB_don3X Y X
1 6 C 3.8067 -0.8797 0.3827 -0.1543 0 0
2 7 N 4.8676 0.1003 0.4087 0.1463 0 0
36 C 4.4722 1.2320 -0.3291 -0.1027 0 0
4 6 C 3.2115 1.0194 -0.8213 -0.1960 0 0
5 7 N 2.7705 -0.2543 -0.4070 0.1856 0 0
6 6 C 6.1346 -0.0515 1.0801 -0.1904 0 0
7 6 C 1.4936 -0.8517 -0.7330 -0.1593 0 0
8 6 C 0.3430 -0.0167 -0.1601 0.1314 0 0
9 6 C -1.0138 -0.6502 -0.4892 0.0521 0 0
10 1 H 5.0726 2.1196 -0.4796 0.2065 0 0.2228
11 1 H 2.6434 1.7105 -1.4299 0.2459 0 0.2305
12 1 H 3.7909 -1.8820 0.8598 0.2615 0 1.4663
13 1 H 1.4442 -1.8775 -0.3056 0.1012 0 0
14 1 H 1.3987 -0.9270 -1.8379 0.0965 0 0.0032
15 1 H 0.3800 1.0088 -0.5879 -0.0254 00
16 1 H 0.4612 0.0519 0.9438 -0.0193 00
17 1 H 6.9596 0.0205 0.3409 0.1261 0 0.024
18 1 H 6.1894 -1.0389 1.5857 0.1310 0 0
19 1 H 6.2521 0.7489 1.8404 0.1273 0 0
20 1 H -1.1279 -0.7191 -1.5937 0.0003 0 0
21 6 C -2.1643 0.1834 0.0873 0.0089 0 0
22 1 H -1.0537 -1.6760 -0.0606 -0.0032 0 0
23 1 H -2.1248 1.2093 -0.3412 0.0007 0 0
24 1 H -2.0497 0.2523 1.1918 -0.0003 0 0
25 6 C -3.5215 -0.4500 -0.2415 -0.0301 0 0
26 1 H -3.6362 -0.5189 -1.3460 0.0017 0 0
27 6 C -4.6720 0.3835 0.3353 0.0150 0 0
28 1 H -3.5610 -1.4759 0.1870 0.0033 0 0
29 1 H -4.6328 1.4094 -0.0933 -0.0006 0 0
30 1 H -4.5575 0.4523 1.4397 0.0006 0 0
31 6 C -6.0285 -0.2504 0.0062 0.1701 0 0
32 1 H -6.1513 -0.3190 -1.0968 -0.0288 0 0
33 6 C -7.1762 0.5762 0.5787 -0.2158 0 0
34 1 H -6.0760 -1.2752 0.4349 -0.0305 0 0
35 1 H -7.1658 1.6008 0.1495 0.0450 0 0
36 1 H -7.0904 0.6426 1.6843 0.0453 0 0
37 1 H -8.1442 0.0946 0.3257 0.0545 0 0
Table S12. Atom coordinates, electrostatic potential-derived CHelpG charges, and sigma moment
for [C9C1im]+ cation calculated at the BP_TZVP level of theory.
Centre Number
Atomic Numbe
rAtom
Coordinate/ÅCHelpG HB_acc3 HB_don3X Y X
1 6 C 4.3973 -0.8891 0.3814 -0.1626 0 0
2 7 N 5.4604 0.0877 0.4270 0.1517 0 0
36 C 5.0723 1.2303 -0.2979 -0.1073 0 0
4 6 C 3.8141 1.0275 -0.8004 -0.1902 0 0
5 7 N 3.3674 -0.2505 -0.4059 0.1691 0 0
6 6 C 6.7229 -0.0762 1.1039 -0.1893 0 0
7 6 C 2.0910 -0.8401 -0.7475 -0.1258 0 0
8 6 C 0.9391 -0.0099 -0.1703 0.1771 0 0
9 6 C -0.4174 -0.6351 -0.5159 -0.0042 0 0
10 1 H 5.6758 2.1183 -0.4329 0.2079 0 0.2544
11 1 H 3.2513 1.7283 -1.4031 0.2436 0 0.2291
12 1 H 4.3761 -1.8976 0.8449 0.2657 0 1.387
13 1 H 2.0364 -1.8714 -0.3342 0.0905 0 0
14 1 H 2.0024 -0.9003 -1.8539 0.0893 0 0.0205
15 1 H 0.9813 1.0212 -0.5840 -0.0353 0 0
16 1 H 1.0509 0.0436 0.9351 -0.0307 0 0
17 1 H 7.5526 0.0035 0.3707 0.1262 0 0.0087
18 1 H 6.7723 -1.0705 1.5965 0.1299 0 0
19 1 H 6.8378 0.7136 1.8756 0.1270 0 0
20 1 H -0.5251 -0.6889 -1.6219 0.0064 0 0
21 6 C -1.5690 0.1938 0.0650 -0.0229 0 0
22 1 H -0.4625 -1.6665 -0.1014 0.0064 0 0
23 1 H -1.5242 1.2252 -0.3494 0.0080 0 0
24 1 H -1.4607 0.2475 1.1709 0.0082 0 0
25 6 C -2.9259 -0.4313 -0.2803 0.1046 0 0
26 1 H -3.0342 -0.4849 -1.3862 -0.0211 0 0
27 6 C -4.0775 0.3977 0.3009 -0.0532 0 0
28 1 H -2.9708 -1.4627 0.1341 -0.0211 0 0
29 1 H -4.0327 1.4291 -0.1135 0.0041 0 0
30 1 H -3.9690 0.4514 1.4069 0.0036 0 0
31 6 C -5.4344 -0.2273 -0.0442 -0.0041 0 0
32 1 H -5.5432 -0.2809 -1.1501 0.0022 00
33 6 C -6.5852 0.6019 0.5374 0.1945 00
34 1 H -5.4795 -1.2587 0.3703 0.0023 0 0
35 1 H -6.5485 1.6336 0.1244 -0.0364 0 0
36 1 H -6.4848 0.6566 1.6435 -0.0359 0 0
37 6 C -7.9376 -0.0169 0.1961 -0.2235 0 0
38 1 H -8.0740 -0.0635 -0.9054 0.0468 0 0
39 1 H -8.7506 0.6032 0.6291 0.0526 0 0
40 1 H -8.0101 -1.0425 0.6167 0.0459 0 0
Table S13. Atom coordinates, electrostatic potential-derived CHelpG charges, and sigma moment
for [C10C1im]+ cation calculated at the BP_TZVP level of theory.
Centre Number
Atomic Numbe
rAtom
Coordinate/ÅCHelpG HB_acc3 HB_don3X Y X
1 6 C -4.9996 0.7208 0.6134 -0.1515 0 0
2 7 N -6.0427 -0.2618 0.4325 0.1349 0 0
3 6 C -5.6456 -1.1842 -0.5539 -0.0964 0 0
4 6 C -4.4007 -0.8362 -1.0076 -0.2041 0 0
5 7 N -3.9717 0.3172 -0.3189 0.1889 0 0
6 6 C -7.2960 -0.2967 1.1447 -0.1791 0 0
7 6 C -2.7134 1.0016 -0.5225 -0.1698 0 0
8 6 C -1.5354 0.0828 -0.1801 0.1602 0 0
9 6 C -0.1978 0.8048 -0.3802 0.0515 0 0
10 1 H -6.2342 -2.0262 -0.8939 0.2061 0 0.2441
11 1 H -3.8354 -1.3558 -1.7699 0.2481 0 0.2316
12 1 H -4.9896 1.5864 1.3084 0.2619 0 1.4361
13 1 H -2.6713 1.9021 0.1291 0.1017 0 0
14 1 H -2.6459 1.3316 -1.5818 0.0991 0 0.0024
15 1 H -1.5650 -0.8171 -0.8323 -0.0303 00
16 1 H -1.6260 -0.2410 0.8802 -0.0239 00
17 1 H -8.1368 -0.2144 0.4245 0.1243 0 0.0148
18 1 H -7.3558 0.5462 1.8654 0.1281 0 0
19 1 H -7.3821 -1.2531 1.7017 0.1253 0 0
20 1 H -0.1113 1.1290 -1.4409 0.0000 0 0
21 6 C 0.9803 -0.1135 -0.0341 -0.0814 0 0
22 1 H -0.1652 1.7049 0.2729 -0.0026 0 0
23 1 H 0.9480 -1.0136 -0.6871 0.0197 0 0
24 1 H 0.8933 -0.4377 1.0266 0.0187 0 0
25 6 C 2.3181 0.6085 -0.2341 0.0462 0 0
26 1 H 2.4050 0.9327 -1.2947 -0.0072 0 0
27 6 C 3.4962 -0.3097 0.1121 0.0917 0 0
28 1 H 2.3503 1.5086 0.4189 -0.0071 0 0
29 1 H 3.4640 -1.2098 -0.5409 -0.0215 0 0
30 1 H 3.4093 -0.6339 1.1728 -0.0202 0 0
31 6 C 4.8340 0.4125 -0.0878 -0.0667 0 0
32 1 H 4.9210 0.7366 -1.1485 0.0050 0 0
33 6 C 6.0122 -0.5056 0.2585 0.0188 0 0
34 1 H 4.8661 1.3126 0.5652 0.0052 0 0
35 1 H 5.9804 -1.4057 -0.3946 -0.0045 0 0
36 1 H 5.9256 -0.8297 1.3192 -0.0055 0 0
37 6 C 7.3493 0.2171 0.0584 0.1927 0 0
38 1 H 7.4444 0.5409 -1.0011 -0.0371 0 0
39 6 C 8.5246 -0.6934 0.4021 -0.2235 0 0
40 1 H 7.3895 1.1163 0.7112 -0.0375 0 0
41 1 H 8.5215 -1.5914 -0.2519 0.0449 0 0
42 1 H 8.4665 -1.0147 1.4639 0.0455 0 0
43 1 H 9.4777 -0.1450 0.2483 0.0514 0 0
Table S14. Atom coordinates, electrostatic potential-derived CHelpG charges, and sigma moment
for [C11C1im]+ cation calculated at the BP_TZVP level of theory.
Centre Number
Atomic Number Atom
Coordinate/ÅCHelpG HB_acc3 HB_don3
X Y X
1 6 C 5.5995 -0.7276 0.6185 -0.1481 0 0
2 7 N 6.6444 0.2550 0.4475 0.1317 0 0
3 6 C 6.2522 1.1833 -0.5353 -0.0910 0 0
4 6 C 5.0087 0.8393 -0.9959 -0.2105 0 0
5 7 N 4.5758 -0.3175 -0.3154 0.1902 0 0
6 6 C 7.8948 0.2845 1.1649 -0.1790 0 0
7 6 C 3.3174 -0.9992 -0.5277 -0.1630 0 0
8 6 C 2.1393 -0.0807 -0.1845 0.1476 0 0
9 6 C 0.8014 -0.7998 -0.3937 0.0517 0 0
10 1 H 6.8430 2.0266 -0.8682 0.2048 0 0.2364
11 1 H 4.4470 1.3639 -1.7575 0.2502 0 0.2299
12 1 H 5.5858 -1.5969 1.3088 0.2602 0 1.4504
13 1 H 3.2717 -1.9033 0.1186 0.1003 0 0
14 1 H 3.2535 -1.3231 -1.5892 0.0975 0 0.0024
15 1 H 2.1726 0.8228 -0.8314 -0.0291 00
16 1 H 2.2264 0.2369 0.8779 -0.0220 00
17 1 H 8.7385 0.2055 0.4477 0.1243 0 0.0154
18 1 H 7.9508 -0.5625 1.8812 0.1283 0 0
19 1 H 7.9796 1.2377 1.7277 0.1253 0 0
20 1 H 0.7184 -1.1177 -1.4565 -0.0011 0 0
21 6 C -0.3765 0.1184 -0.0466 -0.0347 0 0
22 1 H 0.7651 -1.7035 0.2541 -0.0029 0 0
23 1 H -0.3404 1.0222 -0.6943 0.0104 0 0
24 1 H -0.2929 0.4363 1.0162 0.0085 0 0
25 6 C -1.7147 -0.6002 -0.2556 0.0122 0 0
26 1 H -1.7983 -0.9181 -1.3184 -0.0029 0 0
27 6 C -2.8924 0.3181 0.0917 0.0383 0 0
28 1 H -1.7508 -1.5040 0.3921 -0.0035 0 0
29 1 H -2.8563 1.2219 -0.5559 -0.0097 0 0
30 1 H -2.8087 0.6360 1.1546 -0.0081 0 0
31 6 C -4.2308 -0.4003 -0.1171 0.0731 0 0
32 1 H -4.3146 -0.7181 -1.1799 -0.0195 0 0
33 6 C -5.4084 0.5182 0.2304 -0.0585 0 0
34 1 H -4.2670 -1.3041 0.5306 -0.0187 0 0
35 1 H -5.3723 1.4220 -0.4172 0.0025 0 0
36 1 H -5.3246 0.8360 1.2932 0.0026 0 0
37 6 C -6.7469 -0.2001 0.0217 0.0204 0 0
38 1 H -6.8311 -0.5179 -1.0412 -0.0026 0 0
39 6 C -7.9237 0.7187 0.3694 0.1780 0 0
40 1 H -6.7834 -1.1039 0.6694 -0.0044 0 0
41 1 H -7.8957 1.6230 -0.2771 -0.0334 0 0
42 1 H -7.8479 1.0374 1.4320 -0.0339 0 0
43 6 C -9.2578 0.0074 0.1630 -0.2212 0 0
44 1 H -9.3698 -0.3031 -0.8978 0.0439 0 0
45 1 H -10.0903 0.6951 0.4218 0.0505 0 0
46 1 H -9.3220 -0.8898 0.8148 0.0454 0 0
Table S15. Atom coordinates, electrostatic potential-derived CHelpG charges, and sigma moment
for [C2C2im]+ cation calculated at the BP_TZVP level of theory.
Centre Number
Atomic Numbe
rAtom
Coordinate/ÅCHelpG HB_acc3 HB_don3X Y X
1 6 C 0.0000 -0.9887 -0.0005 -0.1140 0 0
2 7 N 1.1107 -0.1005 0.2547 0.0830 0 0
3 6 C 0.6671 1.2340 0.1544 -0.1298 0 0
4 6 C -0.6672 1.2340 -0.1546 -0.1295 0 0
57 N -1.1108 -0.1004 -0.2553 0.0826 0 0
6 6 C 2.4574 -0.5190 0.5777 0.0509 0 0
7 6 C -2.4577 -0.5188 -0.5776 0.0511 0 0
8 6 C -3.4444 -0.0329 0.4794 -0.1038 0 0
9 1 H -4.4682 -0.3738 0.2179 0.0829 0 0
10 1 H 1.2847 2.1106 0.2987 0.2228 0 0.2471
11 1 H -1.2848 2.1108 -0.2986 0.2227 0 0.2422
12 1 H -0.0001 -2.0989 -0.0004 0.2486 0 1.4753
13 1 H -2.5063 -1.6285 -0.6241 0.0734 0 0.0067
14 1 H -2.7424 -0.1128 -1.5719 0.0651 0 0
15 1 H -3.4442 1.0760 0.5335 0.0436 0 0
16 1 H -3.1713 -0.4467 1.4733 0.0445 0 0
17 6 C 3.4448 -0.0327 -0.4785 -0.1032 0 0
18 1 H 2.5060 -1.6288 0.6237 0.0735 0 0.0056
19 1 H 2.7415 -0.1135 1.5723 0.0650 0 0
20 1 H 3.1724 -0.4461 -1.4728 0.0444 0 0
21 1 H 4.4685 -0.3737 -0.2164 0.0828 0 0
22 1 H 3.4447 1.0762 -0.5322 0.0435 0 0
Table S16. Atom coordinates, electrostatic potential-derived CHelpG charges, and sigma moment
for [C3C3im]+ cation calculated at the BP_TZVP level of theory.
Centre Number
Atomic Numbe
rAtom
Coordinate/ÅCHelpG HB_acc3 HB_don3X Y X
1 6 C 0.0000 -0.8893 -0.0001 -0.0921 0 0
2 7 N 1.1068 -0.0010 0.2719 0.1049 0 0
3 6 C 0.6647 1.3334 0.1647 -0.1491 0 0
4 6 C -0.6647 1.3334 -0.1647 -0.1491 0 0
57 N -1.1068 -0.0010 -0.2720 0.1049 0 0
6 6 C 2.4485 -0.4196 0.6152 -0.1375 0 0
7 6 C -2.4486 -0.4195 -0.6153 -0.1375 0 0
8 6 C -3.4532 0.0691 0.4337 0.2549 0 0
9 6 C -4.8708 -0.3777 0.0892 -0.2235 0 0
10 1 H 1.2799 2.2101 0.3185 0.2288 0 0.2403
11 1 H -1.2799 2.2102 -0.3184 0.2288 0 0.2345
12 1 H 0.0000 -1.9994 -0.0001 0.2426 0 1.4794
13 1 H -2.4894 -1.5300 -0.6658 0.1029 0 0.003
14 1 H -2.7118 -0.0129 -1.6158 0.1026 0 0
15 1 H -3.4328 1.1788 0.4884 -0.0323 0 0
16 1 H -3.1761 -0.3420 1.4288 -0.0336 0 0
17 6 C 3.4532 0.0692 -0.4336 0.2549 0 0
18 1 H 2.4893 -1.5301 0.6656 0.1029 0 0.0024
19 1 H 2.7117 -0.0130 1.6158 0.1026 0 0
20 1 H 3.1762 -0.3419 -1.4287 -0.0336 0 0
21 6 C 4.8708 -0.3777 -0.0890 -0.2235 0 0
22 1 H 3.4328 1.1789 -0.4883 -0.0323 0 0
23 1 H 4.9279 -1.4865 -0.0507 0.0632 0 0
24 1 H 5.1780 0.0380 0.8943 0.0624 0 0
25 1 H 5.5754 -0.0123 -0.8655 0.0811 0 0
26 1 H -5.1781 0.0381 -0.8941 0.0624 0 0
27 1 H -5.5753 -0.0124 0.8658 0.0811 0 0
28 1 H -4.9279 -1.4865 0.0508 0.0632 0 0
Table S17. Atom coordinates, electrostatic potential-derived CHelpG charges, and sigma moment
for [C4C4im]+ cation calculated at the BP_TZVP level of theory.
Centre Number
Atomic Numbe
rAtom
Coordinate/ÅCHelpG HB_acc3 HB_don3X Y X
1 6 C -0.0001 -0.9129 -0.0014 -0.1568 0 0
2 7 N -1.0775 -0.0244 -0.3724 0.1800 0 0
3 6 C -0.6470 1.3099 -0.2247 -0.1675 0 0
46 C 0.6469 1.3096 0.2245 -0.1667 0 0
5 7 N 1.0773 -0.0249 0.3709 0.1794 0 0
6 6 C -2.3826 -0.4428 -0.8362 -0.1707 0 0
7 6 C 2.3821 -0.4438 0.8350 -0.1714 0 0
8 6 C 3.4788 0.0448 -0.1178 0.1134 0 0
9 6 C 4.8634 -0.4069 0.3601 0.1904 0 0
10 1 H -1.2455 2.1868 -0.4332 0.2326 0 0.2555
11 1 H 1.2455 2.1863 0.4341 0.2326 0 0.2494
12 1 H -0.0002 -2.0230 -0.0016 0.2621 0 1.4914
13 1 H 2.4177 -1.5543 0.8886 0.0990 0 0.005
14 1 H 2.5529 -0.0377 1.8555 0.0973 0 0
15 1 H 3.4560 1.1550 -0.1718 -0.0141 0 0
16 1 H 3.2854 -0.3666 -1.1330 -0.0148 0 0
17 6 C -3.4786 0.0448 0.1179 0.1143 0 0
18 1 H -2.4183 -1.5532 -0.8910 0.0988 0 0.0056
19 1 H -2.5541 -0.0355 -1.8562 0.0969 0 0
20 1 H -3.2844 -0.3678 1.1325 -0.0153 0 0
21 6 C -4.8636 -0.4065 -0.3593 0.1891 0 0
22 1 H -3.4558 1.1549 0.1732 -0.0142 0 0
23 1 H -4.8976 -1.5166 -0.4125 -0.0223 0 0
24 1 H -5.0619 0.0057 -1.3728 -0.0225 0 0
25 6 C -5.9569 0.0741 0.5905 -0.2780 0 0
26 1 H 5.0609 0.0041 1.3743 -0.0228 0 0
27 6 C 5.9576 0.0748 -0.5881 -0.2781 0 0
28 1 H 4.8974 -1.5171 0.4121 -0.0227 0 0
29 1 H -5.7947 -0.3417 1.6078 0.0702 0 0
30 1 H -6.9471 -0.2664 0.2210 0.0871 0 0
31 1 H -5.9602 1.1836 0.6458 0.0687 0 0
32 1 H 5.9609 1.1844 -0.6421 0.0687 0 0
33 1 H 5.7964 -0.3398 -1.6060 0.0700 0 0
34 1 H 6.9475 -0.2660 -0.2181 0.0871 0 0
Table S18. Atom coordinates, electrostatic potential-derived CHelpG charges, and sigma moment
for [C5C5im]+ cation calculated at the BP_TZVP level of theory.
Centre Number
Atomic Numbe
rAtom
Coordinate/ÅCHelpG HB_acc3 HB_don3X Y X
1 6 C 0.0001 -0.8566 0.0013 -0.1514 0 0
2 7 N 1.0757 0.0319 0.3773 0.1486 0 0
3 6 C 0.6459 1.3662 0.2274 -0.1574 0 0
4 6 C -0.6458 1.3659 -0.2277 -0.1573 0 0
5 7 N -1.0756 0.0314 -0.3759 0.1483 0 0
6 6 C 2.3787 -0.3864 0.8472 -0.0834 0 0
7 6 C -2.3783 -0.3876 -0.8458 -0.0833 0 0
8 6 C -3.4792 0.1015 0.1020 0.0996 0 0
9 6 C -4.8623 -0.3497 -0.3815 -0.0117 0 0
10 1 H 1.2435 2.2431 0.4387 0.2296 0 0.2505
11 1 H -1.2434 2.2425 -0.4402 0.2296 0 0.2513
12 1 H 0.0002 -1.9668 0.0018 0.2598 0 1.4868
13 1 H -2.4138 -1.4981 -0.8994 0.0831 0 0.0046
14 1 H -2.5445 0.0184 -1.8672 0.0789 0 0
15 1 H -3.4562 1.2117 0.1559 -0.0190 0 0
16 1 H -3.2902 -0.3098 1.1181 -0.0183 0 0
17 6 C 3.4791 0.1014 -0.1018 0.1004 0 0
18 1 H 2.4142 -1.4968 0.9021 0.0830 0 0.005
19 1 H 2.5453 0.0210 1.8679 0.0787 0 0
20 1 H 3.2895 -0.3111 -1.1173 -0.0188 0 0
21 6 C 4.8625 -0.3491 0.3814 -0.0117 0 0
22 1 H 3.4560 1.2116 -0.1571 -0.0191 0 0
23 1 H 4.8888 -1.4600 0.4358 0.0166 0 0
24 1 H 5.0482 0.0635 1.3978 0.0177 0 0
25 6 C 5.9618 0.1363 -0.5703 0.1203 0 0
26 1 H -5.0474 0.0616 -1.3985 0.0177 0 0
27 6 C -5.9622 0.1371 0.5689 0.1206 0 0
28 1 H -4.8887 -1.4606 -0.4344 0.0165 0 0
29 1 H 5.7840 -0.2755 -1.5877 -0.0081 0 0
30 6 C 7.3407 -0.3099 -0.0928 -0.2158 0 0
31 1 H 5.9439 1.2467 -0.6267 -0.0096 0 0
32 1 H -5.9444 1.2475 0.6239 -0.0096 0 0
33 1 H -5.7851 -0.2734 1.5870 -0.0083 0 0
34 6 C -7.3408 -0.3097 0.0911 -0.2158 0 0
35 1 H 7.3937 -1.4187 -0.0483 0.0534 0 0
36 1 H 7.5539 0.1066 0.9147 0.0537 0 0
37 1 H 8.1155 0.0549 -0.7996 0.0678 0 0
38 1 H -7.5533 0.1055 -0.9171 0.0537 0 0
39 1 H -8.1161 0.0561 0.7968 0.0677 0 0
40 1 H -7.3939 -1.4185 0.0479 0.0534 0 0
Table S19. Atom coordinates, electrostatic potential-derived CHelpG charges, and sigma moment
for [C6C6im]+ cation calculated at the BP_TZVP level of theory.
Centre Number
Atomic Numbe
rAtom
Coordinate/ÅCHelpG HB_acc3 HB_don3X Y X
1 6 C 0.0000 -0.8820 0.0004 -0.1224 0 0
2 7 N 1.0572 0.0064 0.4257 0.1386 0 0
3 6 C 0.6348 1.3407 0.2569 -0.1586 0 0
4 6 C -0.6347 1.3406 -0.2571 -0.1586 0 0
5 7 N -1.0572 0.0062 -0.4254 0.1386 0 0
6 6 C 2.3371 -0.4122 0.9550 -0.1478 0 0
7 6 C -2.3371 -0.4126 -0.9546 -0.1478 0 0
8 6 C -3.4801 0.0756 -0.0577 0.1871 0 0
9 6 C -4.8396 -0.3758 -0.6039 -0.0191 0 0
10 1 H 1.2220 2.2176 0.4957 0.2316 0 0.2451
11 1 H -1.2220 2.2174 -0.4963 0.2316 0 0.2361
12 1 H 0.0000 -1.9921 0.0005 0.2517 0 1.4966
13 1 H -2.3698 -1.5231 -1.0103 0.0989 0 0.0025
14 1 H -2.4565 -0.0060 -1.9822 0.0974 0 0
15 1 H -3.4599 1.1858 -0.0021 -0.0317 0 0
16 1 H -3.3374 -0.3361 0.9658 -0.0306 0 0
17 6 C 3.4801 0.0757 0.0578 0.1871 0 0
18 1 H 2.3699 -1.5226 1.0112 0.0989 0 0.004
19 1 H 2.4567 -0.0052 1.9824 0.0974 0 0
20 1 H 3.3373 -0.3365 -0.9655 -0.0306 0 0
21 6 C 4.8397 -0.3756 0.6040 -0.0190 0 0
22 1 H 3.4598 1.1858 0.0018 -0.0316 0 0
23 1 H 4.8628 -1.4864 0.6593 0.0082 0 0
24 1 H 4.9784 0.0367 1.6280 0.0085 0 0
25 6 C 5.9825 0.1094 -0.2958 -0.0716 0 0
26 1 H -4.9783 0.0360 -1.6280 0.0085 0 0
27 6 C -5.9826 0.1095 0.2956 -0.0715 0 0
28 1 H -4.8627 -1.4867 -0.6587 0.0082 0 0
29 1 H 5.8436 -0.3029 -1.3198 0.0251 0 0
30 6 C 7.3417 -0.3421 0.2508 0.1914 0 0
31 1 H 5.9601 1.2203 -0.3512 0.0236 0 0
32 1 H -5.9601 1.2204 0.3506 0.0236 0 0
33 1 H -5.8438 -0.3024 1.3197 0.0251 0 0
34 6 C -7.3417 -0.3422 -0.2510 0.1913 0 0
35 1 H 7.3727 -1.4522 0.3054 -0.0272 0 0
36 1 H 7.4890 0.0697 1.2731 -0.0264 0 0
37 6 C 8.4819 0.1385 -0.6423 -0.2284 0 0
38 1 H -7.4888 0.0692 -1.2735 -0.0264 0 0
39 6 C -8.4820 0.1388 0.6417 -0.2284 0 0
40 1 H -7.3726 -1.4524 -0.3051 -0.0272 0 0
41 1 H 8.3715 -0.2770 -1.6666 0.0523 0 0
42 1 H 9.4521 -0.2022 -0.2231 0.0615 0 0
43 1 H 8.4881 1.2481 -0.6970 0.0524 0 0
44 1 H -8.4882 1.2484 0.6960 0.0524 0 0
45 1 H -8.3718 -0.2762 1.6662 0.0523 0 0
46 1 H -9.4521 -0.2020 0.2226 0.0615 0 0
Table S20. Atom coordinates, electrostatic potential-derived CHelpG charges, and sigma moment
for [C7C7im]+ cation calculated at the BP_TZVP level of theory.
Centre Numbe
r
Atomic Numbe
rAtom
Coordinate/ÅCHelpG HB_acc
3HB_don
3X Y X
1 6 C 0.0000 -0.8463 0.0007 -0.1382 0 0
2 7 N 1.0565 0.0422 0.4278 0.1662 0 0
3 6 C 0.6343 1.3765 0.2578 -0.1660 0 0
4 6 C -0.6343 1.3762 -0.2585 -0.1654 0 0
5 7 N -1.0564 0.0418 -0.4272 0.1655 0 0
6 6 C 2.3355 -0.3761 0.9594 -0.1829 0 0
7 6 C -2.3354 -0.3771 -0.9586 -0.1819 0 0
8 6 C -3.4799 0.1119 -0.0641 0.1332 0 0
9 6 C -4.8386 -0.3390 -0.6127 0.1171 0 0
10 1 H 1.2211 2.2534 0.4975 0.2340 0 0.2445
11 1 H -1.2211 2.2529 -0.4990 0.2339 0 0.2316
12 1 H 0.0001 -1.9564 0.0011 0.2568 0 1.469
13 1 H -2.3683 -1.4875 -1.0139 0.1044 0 0.0029
14 1 H -2.4528 0.0291 -1.9866 0.1035 0 0
15 1 H -3.4593 1.2221 -0.0089 -0.0199 0 0
16 1 H -3.3394 -0.2995 0.9598 -0.0186 0 0
17 6 C 3.4799 0.1120 0.0643 0.1337 0 0
18 1 H 2.3684 -1.4865 1.0157 0.1047 0 0.004
19 1 H 2.4530 0.0310 1.9870 0.1036 0 0
20 1 H 3.3392 -0.3003 -0.9592 -0.0187 0 0
21 6 C 4.8387 -0.3384 0.6131 0.1172 0 0
22 1 H 3.4593 1.2222 0.0081 -0.0200 0 0
23 1 H 4.8624 -1.4492 0.6685 -0.0156 0 0
24 1 H 4.9752 0.0740 1.6373 -0.0156 0 0
25 6 C 5.9829 0.1474 -0.2846 -0.1373 0 0
26 1 H -4.9749 0.0725 -1.6373 -0.0157 0 0
27 6 C -5.9830 0.1477 0.2843 -0.1372 0 0
28 1 H -4.8623 -1.4499 -0.6671 -0.0155 0 0
29 1 H 5.8460 -0.2649 -1.3087 0.0286 0 0
30 6 C 7.3421 -0.3026 0.2642 0.0300 0 0
31 1 H 5.9594 1.2583 -0.3400 0.0270 0 0
32 1 H -5.9595 1.2586 0.3388 0.0270 0 0
33 1 H -5.8463 -0.2638 1.3089 0.0285 0 0
34 6 C -7.3421 -0.3028 -0.2643 0.0298 0 0
35 1 H 7.3660 -1.4134 0.3195 0.0002 0 0
36 1 H 7.4792 0.1098 1.2883 0.0017 0 0
37 6 C 8.4855 0.1836 -0.6338 0.1827 0 0
38 1 H -7.4790 0.1087 -1.2888 0.0017 0 0
39 6 C -8.4856 0.1842 0.6331 0.1829 0 0
40 1 H -7.3660 -1.4137 -0.3186 0.0002 0 0
41 1 H 8.3568 -0.2280 -1.6587 -0.0317 0 0
42 6 C 9.8401 -0.2622 -0.0910 -0.2206 0 0
43 1 H 8.4698 1.2940 -0.6907 -0.0313 0 0
44 1 H -8.4700 1.2946 0.6889 -0.0313 0 0
45 1 H -8.3571 -0.2265 1.6583 -0.0318 0 0
46 6 C -9.8401 -0.2621 0.0903 -0.2207 0 0
47 1 H 9.8914 -1.3710 -0.0442 0.0472 0 0
48 1 H 10.0047 0.1541 0.9257 0.0465 0 0
49 1 H 10.6477 0.1031 -0.7598 0.0570 0 0
50 1 H -10.0045 0.1534 -0.9268 0.0466 0 0
51 1 H -10.6479 0.1039 0.7586 0.0570 0 0
52 1 H -9.8915 -1.3709 0.0446 0.0473 0 0
Table S21. Atom coordinates, electrostatic potential-derived CHelpG charges, and sigma moment
for [C8C8im]+ cation calculated at the BP_TZVP level of theory.
Centre Numbe
r
Atomic Numbe
rAtom
Coordinate/ÅCHelpG HB_acc
3HB_don
3X Y X
1 6 C 0.0001 -0.8687 0.0110 -0.1574 0 0
2 7 N 1.0443 0.0248 0.4570 0.1752 0 0
3 6 C 0.6270 1.3570 0.2605 -0.1745 0 0
4 6 C -0.6269 1.3506 -0.2904 -0.1556 0 0
5 7 N -1.0442 0.0141 -0.4558 0.1576 0 0
6 6 C 2.3082 -0.3872 1.0282 -0.1534 0 0
7 6 C -2.3079 -0.4112 -1.0175 -0.1170 0 0
8 6 C -3.4768 0.0868 -0.1602 0.1151 0 0
9 6 C -4.8197 -0.3716 -0.7410 0.0502 0 0
10 1 H 1.2070 2.2367 0.5065 0.2350 0 0.2507
11 1 H -1.2069 2.2243 -0.5568 0.2302 0 0.229
12 1 H 0.0002 -1.9788 0.0238 0.2608 0 1.4836
13 1 H -2.3390 -1.5222 -1.0615 0.0904 0 0.0025
14 1 H -2.3972 -0.0164 -2.0528 0.0854 0 0
15 1 H -3.4584 1.1975 -0.1168 -0.0219 0 0
16 1 H -3.3642 -0.3132 0.8716 -0.0203 0 0
17 6 C 3.4768 0.0906 0.1592 0.1281 0 0
18 1 H 2.3393 -1.4969 1.0981 0.0985 0 0.0048
19 1 H 2.3977 0.0316 2.0540 0.0946 0 0
20 1 H 3.3639 -0.3333 -0.8630 -0.0213 0 0
21 6 C 4.8199 -0.3541 0.7499 0.0532 0 0
22 1 H 3.4584 1.2001 0.0899 -0.0228 0 0
23 1 H 4.8411 -1.4642 0.8186 -0.0033 0 0
24 1 H 4.9288 0.0700 1.7727 -0.0016 0 0
25 6 C 5.9885 0.1206 -0.1219 0.0056 0 0
26 1 H -4.9282 0.0285 -1.7733 -0.0014 0 0
27 6 C -5.9886 0.1233 0.1191 0.0208 0 0
28 1 H -4.8409 -1.4831 -0.7838 -0.0031 0 0
29 1 H 5.8789 -0.3034 -1.1446 0.0013 0 0
30 6 C 7.3318 -0.3243 0.4686 -0.0164 0 0
31 1 H 5.9676 1.2308 -0.1907 0.0001 0 0
32 1 H -5.9677 1.2348 0.1619 -0.0010 0 0
33 1 H -5.8795 -0.2767 1.1514 -0.0001 0 0
34 6 C -7.3317 -0.3352 -0.4615 -0.0441 0 0
35 1 H 7.3526 -1.4344 0.5374 -0.0008 0 0
36 1 H 7.4414 0.0998 1.4913 0.0004 0 0
37 6 C 8.5004 0.1501 -0.4034 -0.0018 0 0
38 1 H -7.4408 0.0649 -1.4939 0.0068 0 0
39 6 C -8.5007 0.1594 0.3986 0.0007 0 0
40 1 H -7.3525 -1.4466 -0.5045 0.0066 0 0
41 1 H 8.3910 -0.2740 -1.4261 0.0041 0 0
42 6 C 9.8430 -0.2952 0.1874 0.1679 0 0
43 1 H 8.4800 1.2603 -0.4722 0.0039 0 0
44 1 H -8.4803 1.2709 0.4415 0.0038 0 0
45 1 H -8.3918 -0.2407 1.4309 0.0039 0 0
46 6 C -9.8430 -0.2995 -0.1824 0.1782 0 0
47 1 H 9.8718 -1.4046 0.2558 -0.0287 0 0
48 1 H 9.9609 0.1284 1.2088 -0.0289 0 0
49 6 C 11.0087 0.1749 -0.6777 -0.2121 0 0
50 1 H -9.9603 0.1001 -1.2134 -0.0308 0 0
51 6 C -11.0092 0.1908 0.6709 -0.2188 0 0
52 1 H -9.8719 -1.4102 -0.2248 -0.0309 0 0
53 1 H 10.9278 -0.2524 -1.7000 0.0447 0 0
54 1 H 11.9662 -0.1610 -0.2268 0.0536 0 0
55 1 H 11.0171 1.2838 -0.7451 0.0449 0 0
56 1 H -11.0175 1.3009 0.7124 0.0460 0 0
57 1 H -10.9288 -0.2125 1.7029 0.0460 0 0
58 1 H -11.9664 -0.1556 0.2275 0.0546 0 0
Table S22. Atom coordinates, electrostatic potential-derived CHelpG charges, and sigma moment
for [C9C9im]+ cation calculated at the BP_TZVP level of theory.
Centre Numbe
r
Atomic Number Atom
Coordinate/ÅCHelpG HB_acc3 HB_don3X Y X
1 6 C 0.0000 -0.8455 0.0045 -0.1497 0 0
2 7 N 1.0439 0.0450 0.4578 0.1641 0 0
3 6 C 0.6266 1.3785 0.2702 -0.1686 0 0
4 6 C -0.6266 1.3759 -0.2821 -0.1605 0 0
5 7 N -1.0438 0.0406 -0.4571 0.1604 0 0
6 6 C 2.3072 -0.3709 1.0274 -0.1560 0 0
7 6 C -2.3070 -0.3807 -1.0229 -0.1504 0 0
8 6 C -3.4766 0.1119 -0.1633 0.1623 0 0
9 6 C -4.8191 -0.3416 -0.7484 0.0178 0 0
10 1 H 1.2063 2.2565 0.5228 0.2341 0 0.2538
11 1 H -1.2064 2.2514 -0.5429 0.2316 0 0.2334
12 1 H 0.0001 -1.9556 0.0097 0.2583 0 1.4677
13 1 H -2.3383 -1.4913 -1.0745 0.0987 0 0.0025
14 1 H -2.3952 0.0212 -2.0556 0.0941 0 0
15 1 H -3.4576 1.2223 -0.1124 -0.0294 0 0
16 1 H -3.3651 -0.2951 0.8658 -0.0279 0 0
17 6 C 3.4766 0.1136 0.1630 0.1668 0 0
18 1 H 2.3386 -1.4810 1.0894 0.0999 0 0.0048
19 1 H 2.3955 0.0406 2.0562 0.0952 0 0
20 1 H 3.3650 -0.3031 -0.8622 -0.0288 0 0
21 6 C 4.8193 -0.3344 0.7521 0.0176 0 0
22 1 H 3.4576 1.2235 0.1016 -0.0304 0 0
23 1 H 4.8413 -1.4450 0.8128 0.0012 0 0
24 1 H 4.9267 0.0824 1.7780 0.0035 0 0
25 6 C 5.9884 0.1477 -0.1150 -0.0394 0 0
26 1 H -4.9264 0.0655 -1.7782 0.0035 0 0
27 6 C -5.9884 0.1486 0.1138 -0.0378 0 0
28 1 H -4.8412 -1.4527 -0.7987 0.0014 0 0
29 1 H 5.8803 -0.2690 -1.1409 0.0130 0 0
30 6 C 7.3315 -0.3000 0.4737 0.0979 0 0
31 1 H 5.9665 1.2583 -0.1758 0.0116 0 0
32 1 H -5.9665 1.2597 0.1642 0.0114 0 0
33 1 H -5.8807 -0.2584 1.1435 0.0125 0 0
34 6 C -7.3314 -0.3045 -0.4711 0.0962 0 0
35 1 H 7.3535 -1.4106 0.5345 -0.0185 0 0
36 1 H 7.4395 0.1167 1.4996 -0.0179 0 0
37 6 C 8.5004 0.1822 -0.3936 -0.0604 0 0
38 1 H -7.4391 0.1025 -1.5008 -0.0183 0 0
39 6 C -8.5006 0.1858 0.3914 -0.0550 0 0
40 1 H -7.3534 -1.4157 -0.5214 -0.0186 0 0
41 1 H 8.3924 -0.2345 -1.4194 0.0067 0 0
42 6 C 9.8437 -0.2654 0.1949 0.0020 0 0
43 1 H 8.4784 1.2928 -0.4544 0.0066 0 0
44 1 H -8.4786 1.2970 0.4417 0.0051 0 0
45 1 H -8.3928 -0.2212 1.4211 0.0052 0 0
46 6 C -9.8437 -0.2672 -0.1933 0.0021 0 0
47 1 H 9.8661 -1.3760 0.2556 0.0009 0 0
48 1 H 9.9521 0.1514 1.2207 0.0010 0 0
49 6 C 11.0118 0.2171 -0.6728 0.1914 0 0
50 1 H -9.9518 0.1399 -1.2230 0.0009 0 0
51 6 C -11.0120 0.2235 0.6695 0.1908 0 0
52 1 H -9.8661 -1.3783 -0.2435 0.0006 0 0
53 1 H 10.9118 -0.1989 -1.6991 -0.0353 0 0
54 6 C 12.3507 -0.2264 -0.0904 -0.2259 0 0
55 1 H 10.9978 1.3272 -0.7348 -0.0353 0 0
56 1 H -10.9980 1.3341 0.7210 -0.0358 0 0
57 1 H -10.9124 -0.1829 1.6997 -0.0356 0 0
58 6 C -12.3508 -0.2254 0.0908 -0.2215 0 0
59 1 H 12.4006 -1.3349 -0.0375 0.0471 0 0
60 1 H 12.4868 0.1942 0.9287 0.0472 0 0
61 1 H 13.1767 0.1361 -0.7379 0.0530 0 0
62 1 H -12.4865 0.1857 -0.9322 0.0459 0 0
63 1 H -13.1769 0.1433 0.7346 0.0518 0 0
64 1 H -12.4007 -1.3343 0.0484 0.0459 0 0
Table S23. Atom coordinates, electrostatic potential-derived CHelpG charges, and sigma moment
for [C10C10im]+ cation calculated at the BP_TZVP level of theory.
Centre Numbe
r
Atomic Numbe
rAtom
Coordinate/ÅCHelpG HB_acc
3HB_don
3X Y X
1 6 C 0.0001 -0.0006 -0.8655 -0.1569 0 0
2 7 N 1.0354 -0.4778 0.0223 0.1634 0 0
3 6 C 0.6216 -0.2904 1.3568 -0.1716 0 0
4 6 C -0.6215 0.2845 1.3574 -0.1719 0 0
5 7 N -1.0352 0.4749 0.0233 0.1632 0 0
6 6 C 2.2882 -1.0679 -0.3970 -0.1365 0 0
7 6 C -2.2878 1.0662 -0.3948 -0.1362 0 0
8 6 C -3.4731 0.2253 0.0923 0.1294 0 0
9 6 C -4.8044 0.8375 -0.3586 0.0667 0 0
10 1 H 1.1966 -0.5586 2.2334 0.2372 0 0
11 1 H -1.1964 0.5509 2.2345 0.2373 0 0
12 1 H 0.0002 0.0008 -1.9756 0.2628 0 0
13 1 H -2.3178 1.1249 -1.5052 0.0930 0 0
14 1 H -2.3572 2.0980 0.0131 0.0926 0 0
15 1 H -3.4557 0.1675 1.2024 -0.0233 0 0.2326
16 1 H -3.3803 -0.8033 -0.3208 -0.0180 0 0.2448
17 6 C 3.4731 -0.2275 0.0918 0.1305 0 1.4541
18 1 H 2.3182 -1.1241 -1.5076 0.0932 0 0.0014
19 1 H 2.3579 -2.1004 0.0086 0.0924 0 0
20 1 H 3.3799 0.8019 -0.3190 -0.0186 0 0
21 6 C 4.8047 -0.8382 -0.3603 0.0670 0 0
22 1 H 3.4557 -0.1721 1.2021 -0.0236 0 0
23 1 H 4.8250 -0.8931 -1.4713 -0.0065 0 0
24 1 H 4.8940 -1.8681 0.0506 -0.0063 0 0
25 6 C 5.9896 0.0051 0.1255 -0.0673 0 0
26 1 H -4.8932 1.8667 0.0546 -0.0062 0 0.0023
27 6 C -5.9897 -0.0061 0.1255 -0.0671 0 0
28 1 H -4.8246 0.8949 -1.4694 -0.0063 0 0
29 1 H 5.8997 1.0350 -0.2854 0.0147 0 0
30 6 C 7.3215 -0.6052 -0.3269 0.0334 0 0
31 1 H 5.9698 0.0601 1.2365 0.0160 0 0
32 1 H -5.9699 -0.0635 1.2363 0.0159 0 0
33 1 H -5.9004 -1.0352 -0.2876 0.0146 0 0
34 6 C -7.3213 0.6059 -0.3256 0.0333 0 0
35 1 H 7.3412 -0.6602 -1.4378 -0.0055 0 0
36 1 H 7.4115 -1.6351 0.0841 -0.0050 0 0
37 6 C 8.5064 0.2384 0.1586 0.0964 0 0
38 1 H -7.4107 1.6350 0.0875 -0.0050 0 0
39 6 C -8.5066 -0.2379 0.1581 0.0983 0 0
40 1 H -7.3410 0.6633 -1.4364 -0.0055 0 0
41 1 H 8.4162 1.2682 -0.2524 -0.0218 0 0
42 6 C 9.8383 -0.3717 -0.2941 -0.0671 0 0
43 1 H 8.4868 0.2934 1.2695 -0.0226 0 0
44 1 H -8.4871 -0.2953 1.2689 -0.0231 0 0
45 1 H -8.4171 -1.2670 -0.2550 -0.0225 0 0
46 6 C -9.8382 0.3740 -0.2933 -0.0676 0 0
47 1 H 9.8578 -0.4268 -1.4050 0.0061 0 0
48 1 H 9.9286 -1.4016 0.1169 0.0058 0 0
49 6 C 11.0231 0.4720 0.1911 0.0100 0 0
50 1 H -9.9278 1.4030 0.1199 0.0055 0 0
51 6 C -11.0236 -0.4699 0.1901 0.0121 0 0
52 1 H -9.8577 0.4314 -1.4041 0.0060 0 0
53 1 H 10.9331 1.5018 -0.2199 -0.0015 0 0
54 6 C 12.3544 -0.1384 -0.2619 0.1843 0 0
55 1 H 11.0040 0.5271 1.3021 -0.0014 0 0
56 1 H -11.0045 -0.5273 1.3010 -0.0019 0 0
57 1 H -10.9342 -1.4990 -0.2231 -0.0018 0 0
58 6 C -12.3545 0.1423 -0.2616 0.1824 0 0
59 1 H 12.3820 -0.1932 -1.3722 -0.0346 0 0
60 1 H 12.4529 -1.1671 0.1486 -0.0338 0 0
61 6 C 13.5362 0.6986 0.2190 -0.2184 0 0
62 1 H -12.4523 1.1702 0.1510 -0.0333 0 0
63 6 C -13.5368 -0.6949 0.2175 -0.2176 0 0
64 1 H -12.3820 0.1993 -1.3718 -0.0344 0 0
65 1 H 13.4747 1.7275 -0.1953 0.0445 0 0
66 1 H 14.4851 0.2339 -0.1229 0.0503 0 0
67 1 H 13.5458 0.7516 1.3285 0.0442 0 0
68 1 H -13.5464 -0.7503 1.3269 0.0440 0 0
69 1 H -13.4760 -1.7230 -0.1989 0.0442 0 0
70 1 H -14.4853 -0.2289 -0.1234 0.0503 0 0
Table S24. Atom coordinates, electrostatic potential-derived CHelpG charges, and sigma moment
for [C11C11im]+ cation calculated at the BP_TZVP level of theory.
Centre Numbe
r
Atomic Numbe
rAtom
Coordinate/ÅCHelpG HB_acc
3HB_don
3X Y X
1 6 C 0.0001 0.0008 -0.8491 -0.1585 0 0
2 7 N 1.0352 -0.4785 0.0379 0.1634 0 0
3 6 C 0.6214 -0.2932 1.3727 -0.1745 0 0
4 6 C -0.6213 0.2823 1.3743 -0.1692 0 0
5 7 N -1.0350 0.4752 0.0404 0.1607 0 0
6 6 C 2.2878 -1.0684 -0.3824 -0.1252 0 0
7 6 C -2.2874 1.0677 -0.3766 -0.1238 0 0
8 6 C -3.4729 0.2266 0.1094 0.1174 0 0
9 6 C -4.8041 0.8403 -0.3398 0.0536 0 0
10 1 H 1.1962 -0.5631 2.2488 0.2382 0 0.2366
11 1 H -1.1962 0.5474 2.2518 0.2369 0 0.243
12 1 H 0.0002 0.0040 -1.9593 0.2632 0 1.458
13 1 H -2.3175 1.1282 -1.4868 0.0906 0 0.0027
14 1 H -2.3562 2.0988 0.0330 0.0899 0 0
15 1 H -3.4552 0.1669 1.2194 -0.0218 0 0
16 1 H -3.3808 -0.8014 -0.3054 -0.0161 0 0
17 6 C 3.4730 -0.2296 0.1084 0.1194 0 0
18 1 H 2.3180 -1.1226 -1.4930 0.0909 0 0.0032
19 1 H 2.3569 -2.1017 0.0214 0.0899 0 0
20 1 H 3.3805 0.8007 -0.3006 -0.0169 0 0
21 6 C 4.8045 -0.8401 -0.3443 0.0542 0 0
22 1 H 3.4552 -0.1761 1.2187 -0.0223 0 0
23 1 H 4.8253 -0.8930 -1.4553 -0.0038 0 0
24 1 H 4.8929 -1.8709 0.0648 -0.0032 0 0
25 6 C 5.9896 0.0015 0.1439 -0.0164 0 0
26 1 H -4.8921 1.8688 0.0750 -0.0030 0 0
27 6 C -5.9896 -0.0034 0.1436 -0.0163 0 0
28 1 H -4.8249 0.8993 -1.4506 -0.0033 0 0
29 1 H 5.9006 1.0322 -0.2651 0.0055 0 0
30 6 C 7.3214 -0.6088 -0.3085 -0.0092 0 0
31 1 H 5.9690 0.0544 1.2550 0.0067 0 0
32 1 H -5.9691 -0.0626 1.2544 0.0066 0 0
33 1 H -5.9012 -1.0319 -0.2711 0.0050 0 0
34 6 C -7.3212 0.6101 -0.3053 -0.0082 0 0
35 1 H 7.3421 -0.6618 -1.4196 0.0014 0 0
36 1 H 7.4104 -1.6396 0.1005 0.0015 0 0
37 6 C 8.5064 0.2329 0.1797 0.0395 0 0
38 1 H -7.4095 1.6386 0.1095 0.0006 0 0
39 6 C -8.5066 -0.2337 0.1782 0.0452 0 0
40 1 H -7.3418 0.6692 -1.4161 0.0010 0 0
41 1 H 8.4173 1.2637 -0.2294 -0.0090 0 0
42 6 C 9.8383 -0.3772 -0.2728 0.0763 0 0
43 1 H 8.4857 0.2858 1.2907 -0.0092 0 0
44 1 H -8.4859 -0.2928 1.2889 -0.0104 0 0
45 1 H -8.4182 -1.2621 -0.2366 -0.0102 0 0
46 6 C -9.8382 0.3798 -0.2708 0.0696 0 0
47 1 H 9.8590 -0.4301 -1.3838 -0.0196 0 0
48 1 H 9.9274 -1.4079 0.1362 -0.0195 0 0
49 6 C 11.0232 0.4647 0.2154 -0.0520 0 0
50 1 H -9.9266 1.4083 0.1440 -0.0180 0 0
51 6 C -11.0237 -0.4640 0.2128 -0.0512 0 0
52 1 H -9.8589 0.4390 -1.3815 -0.0185 0 0
53 1 H 10.9341 1.4955 -0.1936 0.0014 0 0
54 6 C 12.3552 -0.1452 -0.2370 0.0102 0 0
55 1 H 11.0026 0.5176 1.3265 0.0004 0 0
56 1 H -11.0030 -0.5231 1.3235 0.0006 0 0
57 1 H -10.9353 -1.4924 -0.2020 0.0014 0 0
58 6 C -12.3553 0.1495 -0.2361 0.0123 0 0
59 1 H 12.3762 -0.1981 -1.3481 -0.0020 0 0
60 1 H 12.4447 -1.1760 0.1721 -0.0010 0 0
61 6 C 13.5394 0.6970 0.2514 0.1792 0 0
62 1 H -12.4440 1.1779 0.1787 -0.0015 0 0
63 6 C -13.5400 -0.6947 0.2477 0.1780 0 0
64 1 H -12.3763 0.2085 -1.3469 -0.0020 0 0
65 1 H 13.4584 1.7281 -0.1569 -0.0329 0 0
66 6 C 14.8671 0.0931 -0.1969 -0.2284 0 0
67 1 H 13.5269 0.7510 1.3620 -0.0325 0 0
68 1 H -13.5274 -0.7549 1.3579 -0.0322 0 0
69 1 H -13.4597 -1.7235 -0.1664 -0.0327 0 0
70 6 C -14.8673 -0.0874 -0.1972 -0.2309 0 0
71 1 H 14.9158 0.0476 -1.3058 0.0474 0 0
72 1 H 14.9844 -0.9314 0.2161 0.0468 0 0
73 1 H 15.7051 0.7224 0.1701 0.0520 0 0
74 1 H -14.9838 0.9350 0.2216 0.0476 0 0
75 1 H -15.7057 -0.7181 0.1664 0.0529 0 0
76 1 H -14.9160 -0.0356 -1.3058 0.0479 0 0