Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010300948X/de1210sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S010827010300948X/de1210Isup2.hkl |
CCDC reference: 214413
1,4,7-Tri(2-cyanoethyl)-1,4,7-triazacyclononane, (II), was prepared according to the method described by Bushnell et al. (1998). Compound (II) (0.1 mmol) was resolved? in methane (2 ml), and the solvent Mn(DMSO)6(ClO4)3 (0.1 mmol; DMSO is dimethyl sulfoxide) in methane (5 ml) was added dropwise. The resulting gray solid was removed by filtration. Single crystals of (I) were obtained by slow evaporation of the solvent. 1HNMR (CH3CN, p.p.m.): δ 2.75 (t, 6H, CH2—CN), 2.94 (m, 12H, N—CH2—CH2—N), 3.23 (t, 6H, N—CH2).
The positions of all H atoms were fixed geometrically, and H atoms were refined as riding, with C—H distances of 0.97 Å and N—H distances of 0.91 Å.
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C15H25N6+·ClO4− | F(000) = 2472 |
Mr = 388.86 | Dx = 1.338 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2265 reflections |
a = 12.973 (7) Å | θ = 2.4–17.2° |
b = 9.708 (6) Å | µ = 0.23 mm−1 |
c = 46.04 (3) Å | T = 293 K |
β = 92.544 (12)° | Block, colourless |
V = 5793 (6) Å3 | 0.32 × 0.22 × 0.15 mm |
Z = 12 |
CCD area detector diffractometer | 10150 independent reflections |
Radiation source: sealed tube | 5150 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
ϕ and ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: empirical (using intensity measurements) SHELXTL (Bruker, 2000)? | h = −15→15 |
Tmin = 0.941, Tmax = 0.966 | k = 0→11 |
28731 measured reflections | l = 0→54 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.091 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.03P)2] where P = (Fo2 + 2Fc2)/3 |
10150 reflections | (Δ/σ)max < 0.001 |
703 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C15H25N6+·ClO4− | V = 5793 (6) Å3 |
Mr = 388.86 | Z = 12 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.973 (7) Å | µ = 0.23 mm−1 |
b = 9.708 (6) Å | T = 293 K |
c = 46.04 (3) Å | 0.32 × 0.22 × 0.15 mm |
β = 92.544 (12)° |
CCD area detector diffractometer | 10150 independent reflections |
Absorption correction: empirical (using intensity measurements) SHELXTL (Bruker, 2000)? | 5150 reflections with I > 2σ(I) |
Tmin = 0.941, Tmax = 0.966 | Rint = 0.032 |
28731 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.091 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.32 e Å−3 |
10150 reflections | Δρmin = −0.24 e Å−3 |
703 parameters |
Experimental. The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C101 | 0.82597 (15) | 1.0969 (2) | 0.24203 (4) | 0.0555 (6) | |
H101 | 0.8343 | 1.1326 | 0.2617 | 0.067* | |
H102 | 0.8300 | 1.1734 | 0.2286 | 0.067* | |
C102 | 0.91004 (15) | 0.9938 (2) | 0.23654 (4) | 0.0516 (6) | |
H103 | 0.9735 | 1.0422 | 0.2328 | 0.062* | |
H104 | 0.9223 | 0.9370 | 0.2537 | 0.062* | |
C103 | 0.89736 (15) | 0.7571 (2) | 0.21622 (4) | 0.0537 (6) | |
H105 | 0.9674 | 0.7419 | 0.2238 | 0.064* | |
H106 | 0.8886 | 0.7086 | 0.1979 | 0.064* | |
C104 | 0.82281 (16) | 0.7012 (2) | 0.23730 (4) | 0.0562 (6) | |
H107 | 0.8278 | 0.6015 | 0.2379 | 0.067* | |
H108 | 0.8403 | 0.7362 | 0.2566 | 0.067* | |
C105 | 0.65848 (16) | 0.7995 (2) | 0.25168 (5) | 0.0590 (6) | |
H109 | 0.6576 | 0.7340 | 0.2676 | 0.071* | |
H110 | 0.5877 | 0.8145 | 0.2447 | 0.071* | |
C106 | 0.70385 (16) | 0.9355 (2) | 0.26293 (4) | 0.0588 (6) | |
H111 | 0.6557 | 0.9799 | 0.2755 | 0.071* | |
H112 | 0.7674 | 0.9181 | 0.2742 | 0.071* | |
C107 | 0.63914 (17) | 1.1216 (2) | 0.23068 (5) | 0.0624 (6) | |
H113 | 0.6419 | 1.1987 | 0.2441 | 0.075* | |
H114 | 0.5744 | 1.0737 | 0.2330 | 0.075* | |
C108 | 0.64223 (19) | 1.1746 (3) | 0.20032 (5) | 0.0762 (7) | |
H115 | 0.7094 | 1.2149 | 0.1974 | 0.091* | |
H116 | 0.6327 | 1.0986 | 0.1868 | 0.091* | |
C109 | 0.5622 (2) | 1.2783 (3) | 0.19419 (6) | 0.0784 (8) | |
C110 | 0.91763 (14) | 0.9560 (2) | 0.18372 (4) | 0.0483 (6) | |
H117 | 0.9000 | 1.0527 | 0.1817 | 0.058* | |
H118 | 0.8813 | 0.9069 | 0.1680 | 0.058* | |
C111 | 1.03173 (15) | 0.9401 (2) | 0.18020 (5) | 0.0586 (6) | |
H119 | 1.0691 | 0.9901 | 0.1956 | 0.070* | |
H120 | 1.0504 | 0.8436 | 0.1819 | 0.070* | |
C112 | 1.06091 (17) | 0.9922 (3) | 0.15208 (6) | 0.0603 (7) | |
C113 | 0.66134 (17) | 0.6404 (2) | 0.21077 (5) | 0.0648 (7) | |
H121 | 0.6236 | 0.5802 | 0.2233 | 0.078* | |
H122 | 0.7112 | 0.5845 | 0.2010 | 0.078* | |
C114 | 0.58685 (18) | 0.7017 (3) | 0.18829 (5) | 0.0719 (7) | |
H123 | 0.5513 | 0.6281 | 0.1777 | 0.086* | |
H124 | 0.5356 | 0.7558 | 0.1979 | 0.086* | |
C115 | 0.6400 (2) | 0.7887 (3) | 0.16800 (6) | 0.0717 (8) | |
N11 | 0.72487 (13) | 1.02756 (18) | 0.23801 (4) | 0.0538 (5) | |
N12 | 0.88029 (11) | 0.90584 (17) | 0.21145 (3) | 0.0452 (4) | |
N13 | 0.71624 (13) | 0.74190 (18) | 0.22855 (4) | 0.0535 (5) | |
H125 | 0.7245 | 0.8141 | 0.2163 | 0.064* | |
N14 | 0.50208 (19) | 1.3593 (3) | 0.18916 (5) | 0.0956 (8) | |
N15 | 1.08328 (15) | 1.0314 (2) | 0.13025 (5) | 0.0731 (6) | |
N16 | 0.68055 (18) | 0.8564 (3) | 0.15315 (5) | 0.0987 (8) | |
C201 | 0.74927 (17) | 0.1787 (3) | 0.11601 (5) | 0.0658 (7) | |
H201 | 0.6827 | 0.1387 | 0.1198 | 0.079* | |
H202 | 0.7787 | 0.2151 | 0.1342 | 0.079* | |
C202 | 0.81872 (19) | 0.0692 (3) | 0.10493 (5) | 0.0768 (7) | |
H203 | 0.8137 | −0.0121 | 0.1170 | 0.092* | |
H204 | 0.8895 | 0.1015 | 0.1066 | 0.092* | |
C203 | 0.6913 (2) | −0.0393 (3) | 0.06929 (6) | 0.0893 (8) | |
H205 | 0.6524 | −0.0333 | 0.0868 | 0.107* | |
H206 | 0.7006 | −0.1357 | 0.0646 | 0.107* | |
C204 | 0.6351 (2) | 0.0343 (3) | 0.04451 (6) | 0.0849 (8) | |
H207 | 0.6679 | 0.0122 | 0.0266 | 0.102* | |
H208 | 0.5647 | 0.0006 | 0.0428 | 0.102* | |
C205 | 0.56906 (17) | 0.2339 (3) | 0.07070 (5) | 0.0690 (7) | |
H209 | 0.5481 | 0.1581 | 0.0828 | 0.083* | |
H210 | 0.5075 | 0.2767 | 0.0621 | 0.083* | |
C206 | 0.62963 (17) | 0.3377 (3) | 0.08887 (5) | 0.0671 (7) | |
H211 | 0.6301 | 0.4252 | 0.0787 | 0.081* | |
H212 | 0.5964 | 0.3516 | 0.1071 | 0.081* | |
C207 | 0.80762 (16) | 0.4073 (2) | 0.09945 (5) | 0.0618 (6) | |
H213 | 0.8110 | 0.4587 | 0.0815 | 0.074* | |
H214 | 0.8758 | 0.3701 | 0.1040 | 0.074* | |
C208 | 0.77976 (17) | 0.5062 (3) | 0.12361 (5) | 0.0676 (7) | |
H215 | 0.7110 | 0.5426 | 0.1195 | 0.081* | |
H216 | 0.7794 | 0.4568 | 0.1419 | 0.081* | |
C209 | 0.8532 (2) | 0.6194 (3) | 0.12610 (6) | 0.0743 (8) | |
C210 | 0.8727 (2) | −0.0529 (3) | 0.06168 (6) | 0.1062 (10) | |
H217 | 0.8410 | −0.1145 | 0.0473 | 0.127* | |
H218 | 0.9046 | −0.1091 | 0.0770 | 0.127* | |
C211 | 0.9528 (3) | 0.0270 (4) | 0.04804 (8) | 0.1292 (12) | |
H219 | 0.9992 | 0.0614 | 0.0635 | 0.155* | |
H220 | 0.9922 | −0.0365 | 0.0366 | 0.155* | |
C212 | 0.9251 (3) | 0.1405 (4) | 0.02982 (9) | 0.1221 (13) | |
C213 | 0.62718 (17) | 0.2677 (3) | 0.02092 (5) | 0.0738 (7) | |
H221 | 0.6347 | 0.3641 | 0.0261 | 0.089* | |
H222 | 0.6843 | 0.2432 | 0.0090 | 0.089* | |
C214 | 0.52851 (19) | 0.2491 (3) | 0.00344 (5) | 0.0861 (8) | |
H223 | 0.5249 | 0.1556 | −0.0040 | 0.103* | |
H224 | 0.4709 | 0.2627 | 0.0159 | 0.103* | |
C215 | 0.5198 (2) | 0.3446 (4) | −0.02061 (7) | 0.0932 (10) | |
N21 | 0.73515 (13) | 0.2917 (2) | 0.09475 (4) | 0.0577 (5) | |
N22 | 0.79333 (18) | 0.0300 (2) | 0.07382 (5) | 0.0815 (6) | |
N23 | 0.63334 (14) | 0.1829 (2) | 0.04806 (4) | 0.0700 (6) | |
H225 | 0.6982 | 0.2012 | 0.0554 | 0.084* | |
N24 | 0.91336 (18) | 0.7030 (2) | 0.12693 (5) | 0.0932 (7) | |
N25 | 0.9094 (2) | 0.2369 (3) | 0.01851 (8) | 0.1342 (11) | |
N26 | 0.5178 (2) | 0.4254 (3) | −0.03876 (5) | 0.1155 (10) | |
C301 | 0.18364 (17) | 0.6636 (2) | 0.13726 (5) | 0.0658 (7) | |
H301 | 0.1100 | 0.6501 | 0.1338 | 0.079* | |
H302 | 0.1942 | 0.7337 | 0.1521 | 0.079* | |
C302 | 0.23461 (17) | 0.5299 (3) | 0.14700 (5) | 0.0661 (7) | |
H303 | 0.3036 | 0.5483 | 0.1551 | 0.079* | |
H304 | 0.1951 | 0.4872 | 0.1620 | 0.079* | |
C303 | 0.13751 (17) | 0.3769 (2) | 0.11166 (5) | 0.0669 (7) | |
H305 | 0.1316 | 0.2831 | 0.1186 | 0.080* | |
H306 | 0.0820 | 0.4306 | 0.1194 | 0.080* | |
C304 | 0.12883 (18) | 0.3787 (3) | 0.07916 (5) | 0.0705 (7) | |
H307 | 0.1697 | 0.3040 | 0.0717 | 0.085* | |
H308 | 0.0575 | 0.3631 | 0.0728 | 0.085* | |
C305 | 0.10003 (19) | 0.6253 (3) | 0.07286 (5) | 0.0723 (7) | |
H309 | 0.0474 | 0.5983 | 0.0861 | 0.087* | |
H310 | 0.0654 | 0.6546 | 0.0548 | 0.087* | |
C306 | 0.15841 (19) | 0.7431 (3) | 0.08559 (5) | 0.0720 (7) | |
H311 | 0.1097 | 0.8108 | 0.0922 | 0.086* | |
H312 | 0.1973 | 0.7857 | 0.0705 | 0.086* | |
C307 | 0.30984 (18) | 0.8152 (2) | 0.11578 (5) | 0.0698 (7) | |
H313 | 0.3318 | 0.8144 | 0.1362 | 0.084* | |
H314 | 0.2793 | 0.9045 | 0.1114 | 0.084* | |
C308 | 0.40249 (19) | 0.7955 (3) | 0.09765 (5) | 0.0770 (7) | |
H315 | 0.3800 | 0.7802 | 0.0775 | 0.092* | |
H316 | 0.4448 | 0.8779 | 0.0985 | 0.092* | |
C309 | 0.4624 (2) | 0.6796 (3) | 0.10810 (6) | 0.0777 (8) | |
C310 | 0.32738 (18) | 0.3346 (3) | 0.12101 (5) | 0.0749 (7) | |
H317 | 0.3264 | 0.2925 | 0.1019 | 0.090* | |
H318 | 0.3922 | 0.3837 | 0.1238 | 0.090* | |
C311 | 0.32268 (19) | 0.2233 (3) | 0.14347 (6) | 0.0830 (8) | |
H319 | 0.3255 | 0.2623 | 0.1629 | 0.100* | |
H332 | 0.2595 | 0.1705 | 0.1408 | 0.100* | |
C312 | 0.4144 (2) | 0.1348 (3) | 0.13906 (6) | 0.0824 (8) | |
C313 | 0.2085 (2) | 0.4973 (3) | 0.03850 (5) | 0.0851 (8) | |
H321 | 0.2669 | 0.4350 | 0.0398 | 0.102* | |
H322 | 0.2338 | 0.5873 | 0.0330 | 0.102* | |
C314 | 0.1328 (2) | 0.4469 (3) | 0.01528 (6) | 0.0983 (9) | |
H323 | 0.1032 | 0.3604 | 0.0214 | 0.118* | |
H324 | 0.0773 | 0.5132 | 0.0127 | 0.118* | |
C315 | 0.1819 (3) | 0.4269 (3) | −0.01234 (7) | 0.1062 (11) | |
N31 | 0.23100 (14) | 0.70652 (19) | 0.11034 (4) | 0.0617 (5) | |
N32 | 0.23999 (13) | 0.4365 (2) | 0.12196 (4) | 0.0638 (5) | |
N33 | 0.16330 (15) | 0.5074 (2) | 0.06715 (4) | 0.0685 (5) | |
H325 | 0.2202 | 0.5253 | 0.0788 | 0.082* | |
N34 | 0.50849 (19) | 0.5914 (3) | 0.11746 (5) | 0.1034 (8) | |
N35 | 0.48413 (18) | 0.0757 (3) | 0.13599 (5) | 0.0939 (8) | |
N36 | 0.2163 (3) | 0.4116 (3) | −0.03344 (6) | 0.1344 (11) | |
Cl1 | 0.97209 (5) | 0.37066 (7) | 0.186080 (14) | 0.06566 (18) | |
O11 | 0.87181 (17) | 0.3970 (3) | 0.19581 (5) | 0.1484 (9) | |
O12 | 0.95953 (15) | 0.3190 (2) | 0.15799 (4) | 0.1155 (7) | |
O13 | 1.01963 (18) | 0.2737 (2) | 0.20408 (5) | 0.1442 (9) | |
O14 | 1.02135 (15) | 0.4965 (2) | 0.18619 (4) | 0.1192 (7) | |
Cl2 | 0.27955 (6) | 0.05891 (8) | 0.039000 (16) | 0.0780 (2) | |
O21 | 0.3214 (3) | −0.0590 (3) | 0.03311 (5) | 0.1945 (14) | |
O22 | 0.2823 (3) | 0.1527 (3) | 0.01694 (6) | 0.1950 (12) | |
O23 | 0.1824 (2) | 0.0423 (4) | 0.03893 (10) | 0.2490 (19) | |
O24 | 0.2988 (3) | 0.0952 (3) | 0.06748 (6) | 0.2225 (16) | |
Cl3 | 0.31824 (5) | 0.90705 (8) | 0.208730 (15) | 0.0739 (2) | |
O31 | 0.28191 (16) | 1.0002 (3) | 0.18826 (5) | 0.1536 (9) | |
O32 | 0.32113 (16) | 0.7729 (2) | 0.19764 (4) | 0.1244 (7) | |
O33 | 0.24697 (16) | 0.9043 (2) | 0.23099 (4) | 0.1291 (7) | |
O34 | 0.41152 (16) | 0.9381 (2) | 0.22253 (5) | 0.1394 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C101 | 0.0578 (15) | 0.0500 (16) | 0.0590 (14) | −0.0102 (13) | 0.0043 (11) | −0.0113 (12) |
C102 | 0.0521 (14) | 0.0489 (15) | 0.0532 (14) | −0.0084 (12) | −0.0032 (11) | −0.0046 (12) |
C103 | 0.0550 (14) | 0.0418 (16) | 0.0643 (15) | 0.0077 (11) | 0.0033 (12) | 0.0018 (12) |
C104 | 0.0634 (16) | 0.0435 (15) | 0.0618 (14) | 0.0018 (12) | 0.0030 (12) | 0.0070 (12) |
C105 | 0.0609 (15) | 0.0550 (17) | 0.0618 (15) | −0.0060 (13) | 0.0104 (12) | 0.0037 (13) |
C106 | 0.0617 (15) | 0.0570 (17) | 0.0587 (14) | −0.0064 (12) | 0.0119 (11) | −0.0017 (13) |
C107 | 0.0616 (16) | 0.0569 (17) | 0.0688 (17) | −0.0026 (13) | 0.0046 (12) | −0.0050 (13) |
C108 | 0.0787 (19) | 0.073 (2) | 0.0772 (19) | 0.0063 (15) | 0.0004 (14) | 0.0014 (15) |
C109 | 0.084 (2) | 0.066 (2) | 0.0845 (19) | 0.0013 (17) | −0.0064 (16) | 0.0026 (17) |
C110 | 0.0474 (14) | 0.0445 (15) | 0.0535 (14) | 0.0043 (10) | 0.0060 (10) | −0.0021 (11) |
C111 | 0.0498 (14) | 0.0577 (16) | 0.0692 (16) | 0.0027 (11) | 0.0120 (12) | −0.0039 (13) |
C112 | 0.0526 (15) | 0.0558 (17) | 0.0737 (19) | −0.0004 (12) | 0.0179 (14) | −0.0095 (15) |
C113 | 0.0701 (16) | 0.0581 (18) | 0.0658 (15) | −0.0088 (13) | −0.0005 (13) | 0.0014 (14) |
C114 | 0.0703 (17) | 0.0706 (19) | 0.0740 (17) | −0.0115 (14) | −0.0074 (14) | −0.0011 (15) |
C115 | 0.0657 (19) | 0.074 (2) | 0.0741 (19) | −0.0074 (15) | −0.0082 (15) | 0.0049 (16) |
N11 | 0.0543 (12) | 0.0488 (13) | 0.0589 (12) | −0.0078 (10) | 0.0084 (9) | −0.0046 (10) |
N12 | 0.0500 (10) | 0.0387 (12) | 0.0469 (11) | 0.0024 (9) | 0.0024 (8) | −0.0003 (9) |
N13 | 0.0597 (13) | 0.0478 (13) | 0.0534 (11) | −0.0047 (10) | 0.0058 (10) | 0.0075 (10) |
N14 | 0.102 (2) | 0.0714 (19) | 0.1119 (19) | 0.0078 (14) | −0.0139 (15) | 0.0021 (15) |
N15 | 0.0796 (15) | 0.0562 (15) | 0.0854 (16) | −0.0056 (11) | 0.0272 (12) | −0.0019 (12) |
N16 | 0.0857 (18) | 0.107 (2) | 0.1031 (19) | −0.0073 (14) | −0.0049 (14) | 0.0365 (16) |
C201 | 0.0687 (17) | 0.0668 (19) | 0.0617 (15) | −0.0043 (14) | −0.0001 (13) | 0.0042 (14) |
C202 | 0.0855 (19) | 0.0685 (19) | 0.0763 (19) | 0.0093 (15) | 0.0017 (14) | 0.0168 (15) |
C203 | 0.109 (2) | 0.076 (2) | 0.083 (2) | 0.0065 (19) | 0.0042 (17) | −0.0041 (17) |
C204 | 0.099 (2) | 0.077 (2) | 0.0784 (19) | 0.0005 (17) | −0.0029 (16) | −0.0140 (17) |
C205 | 0.0619 (16) | 0.084 (2) | 0.0606 (15) | 0.0014 (14) | −0.0047 (13) | −0.0103 (14) |
C206 | 0.0606 (17) | 0.0763 (19) | 0.0637 (15) | 0.0064 (14) | −0.0054 (12) | −0.0110 (14) |
C207 | 0.0595 (15) | 0.0612 (17) | 0.0650 (15) | 0.0000 (13) | 0.0075 (12) | −0.0042 (13) |
C208 | 0.0619 (16) | 0.0630 (18) | 0.0780 (17) | −0.0002 (14) | 0.0045 (13) | −0.0112 (14) |
C209 | 0.0634 (19) | 0.063 (2) | 0.0959 (19) | 0.0021 (16) | 0.0010 (15) | −0.0118 (17) |
C210 | 0.118 (3) | 0.085 (2) | 0.117 (2) | 0.034 (2) | 0.031 (2) | 0.0158 (19) |
C211 | 0.113 (3) | 0.099 (3) | 0.178 (3) | 0.035 (2) | 0.041 (2) | 0.030 (3) |
C212 | 0.099 (3) | 0.095 (3) | 0.175 (4) | 0.024 (2) | 0.028 (2) | 0.036 (3) |
C213 | 0.0697 (17) | 0.089 (2) | 0.0622 (16) | 0.0084 (14) | −0.0042 (13) | −0.0104 (15) |
C214 | 0.080 (2) | 0.105 (2) | 0.0711 (18) | 0.0128 (16) | −0.0115 (15) | −0.0121 (18) |
C215 | 0.089 (2) | 0.117 (3) | 0.072 (2) | 0.026 (2) | −0.0087 (18) | −0.010 (2) |
N21 | 0.0538 (13) | 0.0619 (14) | 0.0572 (12) | 0.0019 (11) | −0.0012 (9) | −0.0035 (11) |
N22 | 0.0976 (18) | 0.0690 (17) | 0.0785 (16) | 0.0214 (14) | 0.0111 (13) | 0.0073 (12) |
N23 | 0.0693 (14) | 0.0773 (17) | 0.0627 (14) | 0.0052 (11) | −0.0067 (11) | −0.0152 (13) |
N24 | 0.0793 (17) | 0.0677 (18) | 0.133 (2) | −0.0077 (13) | 0.0086 (15) | −0.0144 (15) |
N25 | 0.109 (2) | 0.101 (3) | 0.193 (3) | −0.0021 (19) | 0.0037 (19) | 0.044 (2) |
N26 | 0.122 (2) | 0.146 (3) | 0.0774 (19) | 0.0350 (19) | −0.0093 (16) | 0.0058 (17) |
C301 | 0.0626 (16) | 0.0672 (19) | 0.0677 (16) | 0.0055 (13) | 0.0040 (13) | −0.0109 (14) |
C302 | 0.0596 (15) | 0.071 (2) | 0.0680 (16) | −0.0039 (14) | 0.0015 (12) | 0.0058 (15) |
C303 | 0.0633 (16) | 0.0553 (17) | 0.0817 (18) | −0.0061 (13) | −0.0035 (13) | 0.0080 (14) |
C304 | 0.0780 (17) | 0.0552 (19) | 0.0778 (19) | −0.0049 (14) | −0.0027 (13) | −0.0011 (14) |
C305 | 0.0815 (18) | 0.0603 (19) | 0.0737 (17) | 0.0121 (16) | −0.0133 (14) | 0.0003 (14) |
C306 | 0.0824 (18) | 0.0557 (18) | 0.0769 (17) | 0.0131 (14) | −0.0086 (14) | −0.0032 (14) |
C307 | 0.0726 (17) | 0.0569 (18) | 0.0801 (17) | 0.0044 (14) | 0.0041 (14) | −0.0073 (14) |
C308 | 0.0782 (19) | 0.068 (2) | 0.0851 (18) | −0.0026 (15) | 0.0104 (15) | −0.0090 (16) |
C309 | 0.070 (2) | 0.081 (3) | 0.083 (2) | 0.0036 (17) | 0.0057 (16) | −0.0136 (18) |
C310 | 0.0622 (17) | 0.0669 (19) | 0.0951 (19) | 0.0022 (14) | −0.0010 (14) | 0.0123 (16) |
C311 | 0.0679 (18) | 0.070 (2) | 0.111 (2) | 0.0019 (15) | 0.0008 (15) | 0.0165 (17) |
C312 | 0.064 (2) | 0.066 (2) | 0.116 (2) | 0.0004 (17) | −0.0125 (18) | 0.0041 (17) |
C313 | 0.110 (2) | 0.071 (2) | 0.0751 (19) | −0.0075 (16) | 0.0074 (17) | −0.0028 (15) |
C314 | 0.131 (3) | 0.085 (2) | 0.078 (2) | −0.0088 (19) | 0.0030 (19) | −0.0017 (17) |
C315 | 0.155 (3) | 0.087 (3) | 0.077 (2) | −0.011 (2) | 0.011 (2) | −0.005 (2) |
N31 | 0.0652 (13) | 0.0527 (14) | 0.0669 (13) | 0.0072 (11) | 0.0017 (11) | −0.0054 (11) |
N32 | 0.0540 (13) | 0.0553 (14) | 0.0818 (14) | −0.0008 (10) | 0.0001 (10) | 0.0019 (12) |
N33 | 0.0829 (14) | 0.0542 (15) | 0.0681 (14) | 0.0004 (12) | −0.0023 (11) | −0.0024 (11) |
N34 | 0.0929 (19) | 0.113 (2) | 0.1036 (19) | 0.0263 (16) | −0.0084 (14) | −0.0082 (17) |
N35 | 0.0695 (17) | 0.0828 (19) | 0.1283 (19) | 0.0127 (14) | −0.0077 (15) | −0.0039 (15) |
N36 | 0.209 (3) | 0.113 (2) | 0.083 (2) | −0.016 (2) | 0.030 (2) | −0.0047 (19) |
Cl1 | 0.0809 (5) | 0.0518 (4) | 0.0638 (4) | −0.0006 (4) | −0.0020 (3) | −0.0024 (4) |
O11 | 0.1226 (18) | 0.152 (2) | 0.177 (2) | −0.0022 (15) | 0.0718 (16) | −0.0020 (17) |
O12 | 0.1377 (17) | 0.1248 (18) | 0.0819 (13) | 0.0248 (13) | −0.0192 (11) | −0.0270 (12) |
O13 | 0.204 (2) | 0.0799 (16) | 0.1398 (18) | 0.0068 (15) | −0.0941 (17) | 0.0033 (14) |
O14 | 0.1395 (17) | 0.0644 (14) | 0.1568 (18) | −0.0216 (13) | 0.0413 (14) | −0.0096 (13) |
Cl2 | 0.0866 (5) | 0.0714 (6) | 0.0768 (5) | 0.0156 (4) | 0.0129 (4) | 0.0034 (4) |
O21 | 0.346 (4) | 0.134 (2) | 0.1063 (17) | 0.136 (3) | 0.047 (2) | 0.0049 (16) |
O22 | 0.291 (4) | 0.128 (2) | 0.169 (2) | 0.045 (2) | 0.053 (2) | 0.059 (2) |
O23 | 0.108 (2) | 0.227 (4) | 0.412 (6) | −0.029 (2) | 0.007 (3) | 0.033 (3) |
O24 | 0.391 (5) | 0.148 (3) | 0.123 (2) | 0.071 (3) | −0.043 (2) | −0.0540 (19) |
Cl3 | 0.0720 (5) | 0.0763 (6) | 0.0724 (4) | 0.0075 (4) | −0.0072 (4) | 0.0004 (4) |
O31 | 0.1253 (18) | 0.164 (2) | 0.171 (2) | 0.0157 (15) | −0.0060 (15) | 0.0938 (19) |
O32 | 0.1571 (19) | 0.1055 (18) | 0.1090 (15) | −0.0002 (14) | −0.0109 (13) | −0.0400 (14) |
O33 | 0.1357 (17) | 0.129 (2) | 0.1268 (17) | 0.0244 (14) | 0.0477 (14) | 0.0066 (14) |
O34 | 0.0928 (15) | 0.125 (2) | 0.195 (2) | −0.0090 (13) | −0.0504 (14) | −0.0282 (16) |
C101—N11 | 1.478 (2) | C210—N22 | 1.439 (3) |
C101—C102 | 1.509 (3) | C210—C211 | 1.461 (4) |
C101—H101 | 0.9700 | C210—H217 | 0.9700 |
C101—H102 | 0.9700 | C210—H218 | 0.9700 |
C102—N12 | 1.474 (2) | C211—C212 | 1.422 (4) |
C102—H103 | 0.9700 | C211—H219 | 0.9700 |
C102—H104 | 0.9700 | C211—H220 | 0.9700 |
C103—N12 | 1.476 (3) | C212—N25 | 1.086 (4) |
C103—C104 | 1.502 (3) | C213—C214 | 1.492 (3) |
C103—H105 | 0.9700 | C213—N23 | 1.495 (3) |
C103—H106 | 0.9700 | C213—H221 | 0.9700 |
C104—N13 | 1.477 (3) | C213—H222 | 0.9700 |
C104—H107 | 0.9700 | C214—C215 | 1.444 (4) |
C104—H108 | 0.9700 | C214—H223 | 0.9700 |
C105—N13 | 1.442 (2) | C214—H224 | 0.9700 |
C105—C106 | 1.527 (3) | C215—N26 | 1.146 (4) |
C105—H109 | 0.9700 | N23—H225 | 0.9100 |
C105—H110 | 0.9700 | C301—N31 | 1.468 (3) |
C106—N11 | 1.489 (2) | C301—C302 | 1.516 (3) |
C106—H111 | 0.9700 | C301—H301 | 0.9700 |
C106—H112 | 0.9700 | C301—H302 | 0.9700 |
C107—N11 | 1.467 (3) | C302—N32 | 1.471 (3) |
C107—C108 | 1.492 (3) | C302—H303 | 0.9700 |
C107—H113 | 0.9700 | C302—H304 | 0.9700 |
C107—H114 | 0.9700 | C303—C304 | 1.496 (3) |
C108—C109 | 1.465 (4) | C303—N32 | 1.507 (3) |
C108—H115 | 0.9700 | C303—H305 | 0.9700 |
C108—H116 | 0.9700 | C303—H306 | 0.9700 |
C109—N14 | 1.124 (3) | C304—N33 | 1.446 (3) |
C110—N12 | 1.468 (2) | C304—H307 | 0.9700 |
C110—C111 | 1.504 (3) | C304—H308 | 0.9700 |
C110—H117 | 0.9700 | C305—N33 | 1.439 (3) |
C110—H118 | 0.9700 | C305—C306 | 1.478 (3) |
C111—C112 | 1.456 (3) | C305—H309 | 0.9700 |
C111—H119 | 0.9700 | C305—H310 | 0.9700 |
C111—H120 | 0.9700 | C306—N31 | 1.489 (3) |
C112—N15 | 1.125 (3) | C306—H311 | 0.9700 |
C113—N13 | 1.448 (3) | C306—H312 | 0.9700 |
C113—C114 | 1.507 (3) | C307—N31 | 1.483 (3) |
C113—H121 | 0.9700 | C307—C308 | 1.506 (3) |
C113—H122 | 0.9700 | C307—H313 | 0.9700 |
C114—C115 | 1.455 (3) | C307—H314 | 0.9700 |
C114—H123 | 0.9700 | C308—C309 | 1.438 (4) |
C114—H124 | 0.9700 | C308—H315 | 0.9700 |
C115—N16 | 1.099 (3) | C308—H316 | 0.9700 |
N13—H125 | 0.9100 | C309—N34 | 1.120 (3) |
C201—N21 | 1.477 (3) | C310—C311 | 1.499 (3) |
C201—C202 | 1.497 (3) | C310—N32 | 1.506 (3) |
C201—H201 | 0.9700 | C310—H317 | 0.9700 |
C201—H202 | 0.9700 | C310—H318 | 0.9700 |
C202—N22 | 1.504 (3) | C311—C312 | 1.489 (4) |
C202—H203 | 0.9700 | C311—H319 | 0.9700 |
C202—H204 | 0.9700 | C311—H332 | 0.9700 |
C203—N22 | 1.491 (3) | C312—N35 | 1.086 (3) |
C203—C204 | 1.506 (3) | C313—N33 | 1.470 (3) |
C203—H205 | 0.9700 | C313—C314 | 1.501 (3) |
C203—H206 | 0.9700 | C313—H321 | 0.9700 |
C204—N23 | 1.453 (3) | C313—H322 | 0.9700 |
C204—H207 | 0.9700 | C314—C315 | 1.460 (4) |
C204—H208 | 0.9700 | C314—H323 | 0.9700 |
C205—N23 | 1.450 (3) | C314—H324 | 0.9700 |
C205—C206 | 1.509 (3) | C315—N36 | 1.097 (3) |
C205—H209 | 0.9700 | N33—H325 | 0.9100 |
C205—H210 | 0.9700 | Cl1—O14 | 1.3785 (19) |
C206—N21 | 1.454 (3) | Cl1—O13 | 1.381 (2) |
C206—H211 | 0.9700 | Cl1—O12 | 1.3899 (19) |
C206—H212 | 0.9700 | Cl1—O11 | 1.418 (2) |
C207—N21 | 1.473 (3) | Cl2—O23 | 1.271 (3) |
C207—C208 | 1.525 (3) | Cl2—O21 | 1.301 (2) |
C207—H213 | 0.9700 | Cl2—O22 | 1.366 (3) |
C207—H214 | 0.9700 | Cl2—O24 | 1.370 (3) |
C208—C209 | 1.455 (4) | Cl3—O31 | 1.374 (2) |
C208—H215 | 0.9700 | Cl3—O34 | 1.375 (2) |
C208—H216 | 0.9700 | Cl3—O32 | 1.400 (2) |
C209—N24 | 1.125 (3) | Cl3—O33 | 1.411 (2) |
N11—C101—C102 | 108.72 (18) | C211—C210—H218 | 108.8 |
N11—C101—H101 | 109.9 | H217—C210—H218 | 107.7 |
C102—C101—H101 | 109.9 | C212—C211—C210 | 119.9 (3) |
N11—C101—H102 | 109.9 | C212—C211—H219 | 107.3 |
C102—C101—H102 | 109.9 | C210—C211—H219 | 107.3 |
H101—C101—H102 | 108.3 | C212—C211—H220 | 107.3 |
N12—C102—C101 | 110.44 (16) | C210—C211—H220 | 107.3 |
N12—C102—H103 | 109.6 | H219—C211—H220 | 106.9 |
C101—C102—H103 | 109.6 | N25—C212—C211 | 171.2 (5) |
N12—C102—H104 | 109.6 | C214—C213—N23 | 113.4 (2) |
C101—C102—H104 | 109.6 | C214—C213—H221 | 108.9 |
H103—C102—H104 | 108.1 | N23—C213—H221 | 108.9 |
N12—C103—C104 | 110.68 (16) | C214—C213—H222 | 108.9 |
N12—C103—H105 | 109.5 | N23—C213—H222 | 108.9 |
C104—C103—H105 | 109.5 | H221—C213—H222 | 107.7 |
N12—C103—H106 | 109.5 | C215—C214—C213 | 111.9 (2) |
C104—C103—H106 | 109.5 | C215—C214—H223 | 109.2 |
H105—C103—H106 | 108.1 | C213—C214—H223 | 109.2 |
N13—C104—C103 | 110.42 (17) | C215—C214—H224 | 109.2 |
N13—C104—H107 | 109.6 | C213—C214—H224 | 109.2 |
C103—C104—H107 | 109.6 | H223—C214—H224 | 107.9 |
N13—C104—H108 | 109.6 | N26—C215—C214 | 175.5 (4) |
C103—C104—H108 | 109.6 | C206—N21—C207 | 112.53 (19) |
H107—C104—H108 | 108.1 | C206—N21—C201 | 116.09 (18) |
N13—C105—C106 | 112.38 (17) | C207—N21—C201 | 114.14 (17) |
N13—C105—H109 | 109.1 | C210—N22—C203 | 109.8 (2) |
C106—C105—H109 | 109.1 | C210—N22—C202 | 112.4 (2) |
N13—C105—H110 | 109.1 | C203—N22—C202 | 113.7 (2) |
C106—C105—H110 | 109.1 | C205—N23—C204 | 115.6 (2) |
H109—C105—H110 | 107.9 | C205—N23—C213 | 113.70 (19) |
N11—C106—C105 | 109.79 (17) | C204—N23—C213 | 116.94 (19) |
N11—C106—H111 | 109.7 | C205—N23—H225 | 102.6 |
C105—C106—H111 | 109.7 | C204—N23—H225 | 102.6 |
N11—C106—H112 | 109.7 | C213—N23—H225 | 102.6 |
C105—C106—H112 | 109.7 | N31—C301—C302 | 107.42 (18) |
H111—C106—H112 | 108.2 | N31—C301—H301 | 110.2 |
N11—C107—C108 | 112.26 (18) | C302—C301—H301 | 110.2 |
N11—C107—H113 | 109.2 | N31—C301—H302 | 110.2 |
C108—C107—H113 | 109.2 | C302—C301—H302 | 110.2 |
N11—C107—H114 | 109.2 | H301—C301—H302 | 108.5 |
C108—C107—H114 | 109.2 | N32—C302—C301 | 109.35 (18) |
H113—C107—H114 | 107.9 | N32—C302—H303 | 109.8 |
C109—C108—C107 | 111.7 (2) | C301—C302—H303 | 109.8 |
C109—C108—H115 | 109.3 | N32—C302—H304 | 109.8 |
C107—C108—H115 | 109.3 | C301—C302—H304 | 109.8 |
C109—C108—H116 | 109.3 | H303—C302—H304 | 108.3 |
C107—C108—H116 | 109.3 | C304—C303—N32 | 109.67 (18) |
H115—C108—H116 | 107.9 | C304—C303—H305 | 109.7 |
N14—C109—C108 | 178.6 (3) | N32—C303—H305 | 109.7 |
N12—C110—C111 | 115.09 (16) | C304—C303—H306 | 109.7 |
N12—C110—H117 | 108.5 | N32—C303—H306 | 109.7 |
C111—C110—H117 | 108.5 | H305—C303—H306 | 108.2 |
N12—C110—H118 | 108.5 | N33—C304—C303 | 112.44 (19) |
C111—C110—H118 | 108.5 | N33—C304—H307 | 109.1 |
H117—C110—H118 | 107.5 | C303—C304—H307 | 109.1 |
C112—C111—C110 | 110.88 (18) | N33—C304—H308 | 109.1 |
C112—C111—H119 | 109.5 | C303—C304—H308 | 109.1 |
C110—C111—H119 | 109.5 | H307—C304—H308 | 107.8 |
C112—C111—H120 | 109.5 | N33—C305—C306 | 113.6 (2) |
C110—C111—H120 | 109.5 | N33—C305—H309 | 108.8 |
H119—C111—H120 | 108.1 | C306—C305—H309 | 108.8 |
N15—C112—C111 | 179.4 (3) | N33—C305—H310 | 108.8 |
N13—C113—C114 | 113.9 (2) | C306—C305—H310 | 108.8 |
N13—C113—H121 | 108.8 | H309—C305—H310 | 107.7 |
C114—C113—H121 | 108.8 | C305—C306—N31 | 114.5 (2) |
N13—C113—H122 | 108.8 | C305—C306—H311 | 108.6 |
C114—C113—H122 | 108.8 | N31—C306—H311 | 108.6 |
H121—C113—H122 | 107.7 | C305—C306—H312 | 108.6 |
C115—C114—C113 | 111.3 (2) | N31—C306—H312 | 108.6 |
C115—C114—H123 | 109.4 | H311—C306—H312 | 107.6 |
C113—C114—H123 | 109.4 | N31—C307—C308 | 112.16 (19) |
C115—C114—H124 | 109.4 | N31—C307—H313 | 109.2 |
C113—C114—H124 | 109.4 | C308—C307—H313 | 109.2 |
H123—C114—H124 | 108.0 | N31—C307—H314 | 109.2 |
N16—C115—C114 | 178.5 (3) | C308—C307—H314 | 109.2 |
C107—N11—C101 | 113.89 (18) | H313—C307—H314 | 107.9 |
C107—N11—C106 | 112.83 (16) | C309—C308—C307 | 110.3 (2) |
C101—N11—C106 | 111.62 (16) | C309—C308—H315 | 109.6 |
C110—N12—C102 | 113.85 (16) | C307—C308—H315 | 109.6 |
C110—N12—C103 | 113.60 (15) | C309—C308—H316 | 109.6 |
C102—N12—C103 | 114.71 (16) | C307—C308—H316 | 109.6 |
C105—N13—C113 | 115.01 (18) | H315—C308—H316 | 108.1 |
C105—N13—C104 | 114.41 (17) | N34—C309—C308 | 176.9 (3) |
C113—N13—C104 | 113.78 (18) | C311—C310—N32 | 113.55 (19) |
C105—N13—H125 | 103.9 | C311—C310—H317 | 108.9 |
C113—N13—H125 | 103.9 | N32—C310—H317 | 108.9 |
C104—N13—H125 | 103.9 | C311—C310—H318 | 108.9 |
N21—C201—C202 | 111.14 (18) | N32—C310—H318 | 108.9 |
N21—C201—H201 | 109.4 | H317—C310—H318 | 107.7 |
C202—C201—H201 | 109.4 | C312—C311—C310 | 105.3 (2) |
N21—C201—H202 | 109.4 | C312—C311—H319 | 110.7 |
C202—C201—H202 | 109.4 | C310—C311—H319 | 110.7 |
H201—C201—H202 | 108.0 | C312—C311—H332 | 110.7 |
C201—C202—N22 | 113.21 (19) | C310—C311—H332 | 110.7 |
C201—C202—H203 | 108.9 | H319—C311—H332 | 108.8 |
N22—C202—H203 | 108.9 | N35—C312—C311 | 176.6 (3) |
C201—C202—H204 | 108.9 | N33—C313—C314 | 112.8 (2) |
N22—C202—H204 | 108.9 | N33—C313—H321 | 109.0 |
H203—C202—H204 | 107.7 | C314—C313—H321 | 109.0 |
N22—C203—C204 | 106.8 (2) | N33—C313—H322 | 109.0 |
N22—C203—H205 | 110.4 | C314—C313—H322 | 109.0 |
C204—C203—H205 | 110.4 | H321—C313—H322 | 107.8 |
N22—C203—H206 | 110.4 | C315—C314—C313 | 111.5 (3) |
C204—C203—H206 | 110.4 | C315—C314—H323 | 109.3 |
H205—C203—H206 | 108.6 | C313—C314—H323 | 109.3 |
N23—C204—C203 | 113.3 (2) | C315—C314—H324 | 109.3 |
N23—C204—H207 | 108.9 | C313—C314—H324 | 109.3 |
C203—C204—H207 | 108.9 | H323—C314—H324 | 108.0 |
N23—C204—H208 | 108.9 | N36—C315—C314 | 178.1 (4) |
C203—C204—H208 | 108.9 | C301—N31—C307 | 111.75 (18) |
H207—C204—H208 | 107.7 | C301—N31—C306 | 116.09 (18) |
N23—C205—C206 | 108.94 (19) | C307—N31—C306 | 111.58 (19) |
N23—C205—H209 | 109.9 | C302—N32—C310 | 119.30 (18) |
C206—C205—H209 | 109.9 | C302—N32—C303 | 114.29 (17) |
N23—C205—H210 | 109.9 | C310—N32—C303 | 113.17 (19) |
C206—C205—H210 | 109.9 | C305—N33—C304 | 115.39 (19) |
H209—C205—H210 | 108.3 | C305—N33—C313 | 118.1 (2) |
N21—C206—C205 | 111.16 (19) | C304—N33—C313 | 115.33 (19) |
N21—C206—H211 | 109.4 | C305—N33—H325 | 101.3 |
C205—C206—H211 | 109.4 | C304—N33—H325 | 101.3 |
N21—C206—H212 | 109.4 | C313—N33—H325 | 101.3 |
C205—C206—H212 | 109.4 | O14—Cl1—O13 | 114.01 (14) |
H211—C206—H212 | 108.0 | O14—Cl1—O12 | 110.99 (13) |
N21—C207—C208 | 114.60 (18) | O13—Cl1—O12 | 110.09 (13) |
N21—C207—H213 | 108.6 | O14—Cl1—O11 | 105.70 (14) |
C208—C207—H213 | 108.6 | O13—Cl1—O11 | 108.96 (16) |
N21—C207—H214 | 108.6 | O12—Cl1—O11 | 106.73 (14) |
C208—C207—H214 | 108.6 | O23—Cl2—O21 | 108.2 (2) |
H213—C207—H214 | 107.6 | O23—Cl2—O22 | 98.1 (2) |
C209—C208—C207 | 110.96 (19) | O21—Cl2—O22 | 114.00 (17) |
C209—C208—H215 | 109.4 | O23—Cl2—O24 | 100.0 (2) |
C207—C208—H215 | 109.4 | O21—Cl2—O24 | 111.44 (17) |
C209—C208—H216 | 109.4 | O22—Cl2—O24 | 122.1 (2) |
C207—C208—H216 | 109.4 | O31—Cl3—O34 | 116.15 (15) |
H215—C208—H216 | 108.0 | O31—Cl3—O32 | 112.09 (16) |
N24—C209—C208 | 176.0 (3) | O34—Cl3—O32 | 109.58 (13) |
N22—C210—C211 | 113.9 (3) | O31—Cl3—O33 | 107.14 (14) |
N22—C210—H217 | 108.8 | O34—Cl3—O33 | 105.08 (15) |
C211—C210—H217 | 108.8 | O32—Cl3—O33 | 106.05 (14) |
N22—C210—H218 | 108.8 |
D—H···A | D—H | H···A | D···A | D—H···A |
N13—H125···N11 | 0.91 | 2.30 | 2.809 (3) | 115 |
N13—H125···N12 | 0.91 | 2.23 | 2.798 (3) | 120 |
N23—H225···N21 | 0.91 | 2.05 | 2.689 (3) | 126 |
N23—H225···N22 | 0.91 | 2.22 | 2.775 (3) | 119 |
N33—H325···N31 | 0.91 | 2.28 | 2.882 (3) | 123 |
N33—H325···N32 | 0.91 | 2.17 | 2.758 (3) | 122 |
C102—H104···O13i | 0.97 | 2.59 | 3.557 (4) | 171 |
C104—H108···O13i | 0.97 | 2.53 | 3.386 (4) | 147 |
C107—H114···O34 | 0.97 | 2.52 | 3.455 (4) | 162 |
C207—H213···N36ii | 0.97 | 2.56 | 3.513 (4) | 169 |
C211—H220···O23iii | 0.97 | 2.58 | 3.030 (5) | 108 |
C301—H301···N24iv | 0.97 | 2.61 | 3.538 (4) | 161 |
C302—H304···O14iv | 0.97 | 2.56 | 3.385 (4) | 143 |
C303—H305···N15v | 0.97 | 2.58 | 3.540 (4) | 169 |
C308—H316···N35vi | 0.97 | 2.62 | 3.387 (4) | 136 |
C310—H317···O24 | 0.97 | 2.50 | 3.396 (4) | 153 |
C310—H318···N34 | 0.97 | 2.54 | 3.435 (4) | 153 |
Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) −x+1, −y+1, −z; (iii) x+1, y, z; (iv) x−1, y, z; (v) x−1, y−1, z; (vi) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C15H25N6+·ClO4− |
Mr | 388.86 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 12.973 (7), 9.708 (6), 46.04 (3) |
β (°) | 92.544 (12) |
V (Å3) | 5793 (6) |
Z | 12 |
Radiation type | Mo Kα |
µ (mm−1) | 0.23 |
Crystal size (mm) | 0.32 × 0.22 × 0.15 |
Data collection | |
Diffractometer | CCD area detector diffractometer |
Absorption correction | Empirical (using intensity measurements) SHELXTL (Bruker, 2000)? |
Tmin, Tmax | 0.941, 0.966 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 28731, 10150, 5150 |
Rint | 0.032 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.091, 1.05 |
No. of reflections | 10150 |
No. of parameters | 703 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.32, −0.24 |
Computer programs: SMART (Bruker, 2000), SMART, SAINT (Bruker, 2000), SHELXTL (Bruker, 2000), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
N13—H125···N11 | 0.9100 | 2.3000 | 2.809 (3) | 115.00 |
N13—H125···N12 | 0.9100 | 2.2300 | 2.798 (3) | 120.00 |
N23—H225···N21 | 0.9100 | 2.0500 | 2.689 (3) | 126.00 |
N23—H225···N22 | 0.9100 | 2.2200 | 2.775 (3) | 119.00 |
N33—H325···N31 | 0.9100 | 2.2800 | 2.882 (3) | 123.00 |
N33—H325···N32 | 0.9100 | 2.1700 | 2.758 (3) | 122.00 |
C102—H104···O13i | 0.9700 | 2.5900 | 3.557 (4) | 171.00 |
C104—H108···O13i | 0.9700 | 2.5300 | 3.386 (4) | 147.00 |
C107—H114···O34 | 0.9700 | 2.5200 | 3.455 (4) | 162.00 |
C207—H213···N36ii | 0.9700 | 2.5600 | 3.513 (4) | 169.00 |
C211—H220···O23iii | 0.9700 | 2.5800 | 3.030 (5) | 108.00 |
C301—H301···N24iv | 0.9700 | 2.6100 | 3.538 (4) | 161.00 |
C302—H304···O14iv | 0.9700 | 2.5600 | 3.385 (4) | 143.00 |
C303—H305···N15v | 0.9700 | 2.5800 | 3.540 (4) | 169.00 |
C308—H316···N35vi | 0.9700 | 2.6200 | 3.387 (4) | 136.00 |
C310—H317···O24 | 0.9700 | 2.5000 | 3.396 (4) | 153.00 |
C310—H318···N34 | 0.9700 | 2.5400 | 3.435 (4) | 153.00 |
Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) −x+1, −y+1, −z; (iii) x+1, y, z; (iv) x−1, y, z; (v) x−1, y−1, z; (vi) x, y+1, z. |
The functionalized pendant-arm derivatives of 1,4,7-triazacyclononane have been used as multidentate ligands for? enzyme simulations (Wieghardt et al., 1989), as models of myoglobin (Collman et al., 1997) and as building blocks for the construction of solid-state architectures (Tei et al., 1998; Tei et al., 2002). We chose to investigate macrocyclic frameworks with cyanoethyl groups as the pendant arms, because we believe that nitrile functionalized pendant-arms will promote the formation of multinuclear compounds that are similar to the active site in some enzymes. We report here the molecular and supramolecular structures of the ligand with C—H···N interactions. Cyano N atoms generally act as an acceptor, via an H atom, for aromatic C atoms? (Boitsov et al., 2002). However, in the supramolecular structure of the title compound, (I), the C—H···N interactions are between the methylene C—H atoms and the cyano N atoms.
The asymmetric unit of (I) consists of three unique molecules. The 1,4,7-tri(2-cyanoethyl)-1,4,7-triazacyclononane ion is protonated in the weak acidic solution of Mn3+, and the H atoms bound to atoms N3, N9 and N15, respectively. The cations and perchlorate anions are shown in Fig. 1.
The supramolecular structure of the ion is generated by a R44(30)S(10) motif and a C(10) chain. Cyano atom N36 of cation 3 (containing atoms C301 etc.) at (x, y, z) acts as an acceptor, via atom H213, for atom C207 of cation 2 (containing atoms C201 etc.) at (1 − x, 3/2 + y, 1/2 − z). Cyano atom N24 of cation 2 at (1 − x, 3/2 + y, 1/2 − z) acts as an acceptor, via atom H301, for atom C301 of cation 3 at (-x, 3/2 + y, 1/2 − z), and cyano atom N36 of cation 3 acts as an acceptor, via atom H213, for atom C207 of cation 2 at (−1 − x, −y, −z). Finally, cyano atom N24 of cation 2 at (−1 + x, y, z) acts as an acceptor, via atom H301, for atom C301 of cation 3 at (x, y, z), thus completing a centrosymmetric R44(30) ring, centered at (0, 1/2, 0). Cation 1 (containing atoms C101 etc.) at (−1 + x, −1 + y, z) and at (1/2 − x, 5/2 + y, 1/2 − z) links the rings? via C303—H305···N15 interactions. A C310—H316···N34 interaction in cation 3 generates an edge-fused S(10) ring (Fig. 2). The propogation of intermolecular C308—H316···N35 interactions between cations 3 produces a C(11) chain running parallel to the [010] direction (Fig. 3). The combination of two C(11) chains and R44(30) rings forms a `column' running parallel to the [010] direction (See Fig. 4).
There are also intermolecular C—H···O hydrogen bonds.