Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805011414/cv6490sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805011414/cv6490Isup2.hkl |
CCDC reference: 271856
Data collection: Enraf–Nonius CAD-4; cell refinement: Enraf–Nonius CAD-4; data reduction: Enraf–Nonius CAD-4; program(s) used to solve structure: coordinates were input directly; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).
C42H54N4 | V = 1837.8 (8) Å3 |
Mr = 614.89 | Z = 2 |
Triclinic, P1 | F(000) = 668 |
Hall symbol: -P 1 | Dx = 1.111 Mg m−3 |
a = 11.915 (3) Å | Mo Kα radiation, λ = 0.71069 Å |
b = 12.050 (4) Å | Cell parameters from 25 reflections |
c = 13.544 (2) Å | µ = 0.07 mm−1 |
α = 105.67 (2)° | T = 293 K |
β = 99.141 (10)° | Prism, yellow |
γ = 93.40 (2)° | 0.45 × 0.35 × 0.32 mm |
Enraf-Nonius CAD-4 diffractometer | 3290 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.026 |
Graphite monochromator | θmax = 27.0°, θmin = 2.0° |
φ or ω scans? | h = 0→15 |
8328 measured reflections | k = −15→15 |
7957 independent reflections | l = −17→17 |
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)] = 0.080 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.270 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.1309P)2 + 0.0377P] where P = (Fo2 + 2Fc2)/3 |
7957 reflections | (Δ/σ)max < 0.001 |
453 parameters | Δρmax = 0.32 e Å−3 |
10 restraints | Δρmin = −0.23 e Å−3 |
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 | Occ. (<1) | |
N51 | 0.0709 (2) | −0.1189 (2) | −0.0652 (2) | 0.0698 (7) | |
N52 | 0.7479 (2) | 0.5612 (2) | 0.3534 (2) | 0.0824 (8) | |
C62 | 0.0593 (2) | −0.0117 (3) | −0.0086 (2) | 0.0594 (8) | |
C63 | 0.1498 (2) | 0.0739 (3) | 0.0333 (2) | 0.0613 (8) | |
H63 | 0.1372 | 0.1469 | 0.0724 | 0.074* | |
C64 | 0.2596 (3) | 0.0515 (3) | 0.0172 (2) | 0.0629 (8) | |
C65 | 0.2711 (3) | −0.0581 (3) | −0.0429 (3) | 0.0726 (9) | |
H65 | 0.3421 | −0.0773 | −0.0582 | 0.087* | |
C66 | 0.1765 (3) | −0.1386 (3) | −0.0800 (3) | 0.0767 (9) | |
H66 | 0.1872 | −0.2126 | −0.1184 | 0.092* | |
C67 | 0.3593 (3) | 0.1375 (3) | 0.0612 (3) | 0.0691 (9) | |
H67 | 0.4215 | 0.1291 | 0.0272 | 0.083* | |
C68 | 0.3681 (3) | 0.2264 (3) | 0.1456 (3) | 0.0694 (9) | |
H68 | 0.3045 | 0.2333 | 0.1778 | 0.083* | |
C69 | 0.4642 (3) | 0.3146 (3) | 0.1945 (2) | 0.0617 (8) | |
C70 | 0.4675 (3) | 0.3889 (3) | 0.2927 (3) | 0.0767 (10) | |
H70 | 0.4052 | 0.3834 | 0.3254 | 0.092* | |
C71 | 0.5586 (3) | 0.4710 (3) | 0.3450 (3) | 0.0817 (10) | |
H71 | 0.5559 | 0.5192 | 0.4108 | 0.098* | |
C72 | 0.6550 (3) | 0.4825 (3) | 0.3000 (3) | 0.0697 (9) | |
C73 | 0.6491 (3) | 0.4119 (3) | 0.1988 (3) | 0.0699 (9) | |
H73 | 0.7093 | 0.4198 | 0.1642 | 0.084* | |
C74 | 0.5579 (3) | 0.3313 (3) | 0.1485 (2) | 0.0670 (8) | |
H74 | 0.5586 | 0.2859 | 0.0811 | 0.080* | |
C75 | 0.8452 (3) | 0.5764 (3) | 0.3047 (3) | 0.0933 (12) | |
H75A | 0.8860 | 0.6527 | 0.3387 | 0.112* | |
H75B | 0.8188 | 0.5713 | 0.2320 | 0.112* | |
C76 | 0.9282 (4) | 0.4816 (4) | 0.3126 (4) | 0.1174 (15) | |
H76A | 0.9599 | 0.4923 | 0.3855 | 0.141* | |
H76B | 0.8845 | 0.4058 | 0.2861 | 0.141* | |
C77 | 1.0174 (5) | 0.4839 (6) | 0.2582 (4) | 0.158 (2) | |
H77A | 1.0625 | 0.5588 | 0.2879 | 0.190* | |
H77B | 0.9846 | 0.4792 | 0.1868 | 0.190* | |
C78 | 1.0974 (4) | 0.3917 (4) | 0.2559 (4) | 0.1320 (18) | |
H78A | 1.1551 | 0.4032 | 0.2165 | 0.198* | |
H78B | 1.0552 | 0.3168 | 0.2238 | 0.198* | |
H78C | 1.1330 | 0.3962 | 0.3258 | 0.198* | |
C79 | 0.7629 (4) | 0.6195 (3) | 0.4633 (3) | 0.1028 (13) | |
H79A | 0.8376 | 0.6045 | 0.4940 | 0.123* | 0.464 (13) |
H79B | 0.7075 | 0.5791 | 0.4902 | 0.123* | 0.464 (13) |
H79C | 0.8430 | 0.6401 | 0.4949 | 0.123* | 0.536 (13) |
H79D | 0.7265 | 0.5734 | 0.5004 | 0.123* | 0.536 (13) |
C80 | 0.7554 (10) | 0.7461 (8) | 0.5086 (10) | 0.109 (5) | 0.464 (13) |
H80A | 0.7884 | 0.7689 | 0.5823 | 0.130* | 0.464 (13) |
H80B | 0.7992 | 0.7902 | 0.4747 | 0.130* | 0.464 (13) |
C81 | 0.6367 (7) | 0.7731 (8) | 0.4953 (10) | 0.087 (4) | 0.464 (13) |
H81A | 0.5925 | 0.7303 | 0.5300 | 0.104* | 0.464 (13) |
H81B | 0.6030 | 0.7508 | 0.4218 | 0.104* | 0.464 (13) |
C80' | 0.6995 (11) | 0.7302 (8) | 0.4586 (8) | 0.118 (5) | 0.536 (13) |
H80C | 0.7350 | 0.7709 | 0.4168 | 0.141* | 0.536 (13) |
H80D | 0.6203 | 0.7059 | 0.4251 | 0.141* | 0.536 (13) |
C81' | 0.7040 (13) | 0.8101 (9) | 0.5648 (9) | 0.171 (7) | 0.536 (13) |
H81C | 0.7823 | 0.8393 | 0.5983 | 0.205* | 0.536 (13) |
H81D | 0.6692 | 0.7712 | 0.6082 | 0.205* | 0.536 (13) |
C82 | 0.6345 (5) | 0.9103 (5) | 0.5449 (5) | 0.161 (2) | |
H82A | 0.5568 | 0.9275 | 0.5440 | 0.241* | 0.464 (13) |
H82B | 0.6701 | 0.9519 | 0.5047 | 0.241* | 0.464 (13) |
H82C | 0.6754 | 0.9334 | 0.6155 | 0.241* | 0.464 (13) |
H82D | 0.6365 | 0.9683 | 0.6098 | 0.241* | 0.536 (13) |
H82E | 0.5567 | 0.8799 | 0.5142 | 0.241* | 0.536 (13) |
H82F | 0.6677 | 0.9444 | 0.4983 | 0.241* | 0.536 (13) |
N1 | 0.0696 (2) | −0.6286 (2) | −0.0418 (2) | 0.0729 (7) | |
N2 | 0.7652 (2) | 0.0539 (2) | 0.3227 (2) | 0.0769 (8) | |
C2 | 0.0599 (3) | −0.5164 (3) | 0.0012 (2) | 0.0629 (8) | |
C3 | 0.1532 (3) | −0.4341 (3) | 0.0455 (2) | 0.0676 (9) | |
H3 | 0.1424 | −0.3568 | 0.0730 | 0.081* | |
C4 | 0.2636 (3) | −0.4674 (3) | 0.0489 (2) | 0.0644 (8) | |
C5 | 0.2722 (3) | −0.5842 (3) | 0.0048 (3) | 0.0746 (9) | |
H5 | 0.3436 | −0.6115 | 0.0050 | 0.089* | |
C6 | 0.1749 (3) | −0.6588 (3) | −0.0390 (3) | 0.0782 (10) | |
H6 | 0.1833 | −0.7362 | −0.0690 | 0.094* | |
C7 | 0.3679 (3) | −0.3873 (3) | 0.0959 (3) | 0.0737 (9) | |
H7 | 0.4356 | −0.4204 | 0.1073 | 0.088* | |
C8 | 0.3753 (3) | −0.2737 (3) | 0.1234 (2) | 0.0717 (9) | |
H8 | 0.3073 | −0.2414 | 0.1110 | 0.086* | |
C9 | 0.4785 (3) | −0.1906 (3) | 0.1717 (2) | 0.0660 (8) | |
C10 | 0.5861 (3) | −0.2246 (3) | 0.1975 (3) | 0.0733 (9) | |
H10 | 0.5948 | −0.3032 | 0.1831 | 0.088* | |
C11 | 0.6801 (3) | −0.1447 (3) | 0.2438 (3) | 0.0770 (10) | |
H11 | 0.7512 | −0.1709 | 0.2577 | 0.092* | |
C12 | 0.6716 (3) | −0.0260 (3) | 0.2706 (2) | 0.0654 (8) | |
C13 | 0.5635 (3) | 0.0079 (3) | 0.2430 (3) | 0.0715 (9) | |
H13 | 0.5541 | 0.0864 | 0.2571 | 0.086* | |
C14 | 0.4716 (3) | −0.0728 (3) | 0.1956 (3) | 0.0731 (9) | |
H14 | 0.4010 | −0.0469 | 0.1787 | 0.088* | |
C15 | 0.8744 (3) | 0.0146 (3) | 0.3592 (3) | 0.0829 (10) | |
H15A | 0.8590 | −0.0528 | 0.3831 | 0.100* | |
H15B | 0.9165 | 0.0754 | 0.4184 | 0.100* | |
C16 | 0.9486 (3) | −0.0162 (3) | 0.2763 (3) | 0.0812 (10) | |
H16A | 0.9030 | −0.0675 | 0.2128 | 0.097* | |
H16B | 0.9753 | 0.0538 | 0.2609 | 0.097* | |
C17 | 1.0506 (3) | −0.0747 (4) | 0.3111 (3) | 0.0979 (12) | |
H17A | 1.0951 | −0.0238 | 0.3754 | 0.118* | |
H17B | 1.0235 | −0.1452 | 0.3256 | 0.118* | |
C18 | 1.1259 (4) | −0.1041 (4) | 0.2315 (3) | 0.1218 (15) | |
H18A | 1.1889 | −0.1411 | 0.2572 | 0.183* | |
H18B | 1.1545 | −0.0345 | 0.2181 | 0.183* | |
H18C | 1.0828 | −0.1557 | 0.1681 | 0.183* | |
C19 | 0.7611 (3) | 0.1778 (3) | 0.3464 (3) | 0.0908 (11) | |
H19A | 0.6937 | 0.1904 | 0.3020 | 0.109* | 0.551 (15) |
H19B | 0.8267 | 0.2093 | 0.3246 | 0.109* | 0.551 (15) |
H19C | 0.7148 | 0.1980 | 0.2894 | 0.109* | 0.449 (15) |
H19D | 0.8373 | 0.2184 | 0.3603 | 0.109* | 0.449 (15) |
C20 | 0.7592 (11) | 0.2505 (9) | 0.4552 (8) | 0.126 (5) | 0.551 (15) |
H20A | 0.8229 | 0.2327 | 0.5005 | 0.152* | 0.551 (15) |
H20B | 0.7755 | 0.3308 | 0.4565 | 0.152* | 0.551 (15) |
C21 | 0.6710 (10) | 0.2448 (14) | 0.4975 (9) | 0.175 (8) | 0.551 (15) |
H21A | 0.6484 | 0.1638 | 0.4898 | 0.210* | 0.551 (15) |
H21B | 0.6091 | 0.2729 | 0.4584 | 0.210* | 0.551 (15) |
C21' | 0.7539 (12) | 0.273 (2) | 0.5290 (9) | 0.255 (14) | 0.449 (15) |
H21C | 0.7875 | 0.3414 | 0.5159 | 0.306* | 0.449 (15) |
H21D | 0.8165 | 0.2351 | 0.5563 | 0.306* | 0.449 (15) |
C20' | 0.7064 (13) | 0.2067 (14) | 0.4442 (11) | 0.198 (12) | 0.449 (15) |
H20C | 0.6351 | 0.2372 | 0.4253 | 0.238* | 0.449 (15) |
H20D | 0.6860 | 0.1333 | 0.4568 | 0.238* | 0.449 (15) |
C22 | 0.6832 (5) | 0.3139 (5) | 0.6172 (4) | 0.156 (2) | |
H22A | 0.6118 | 0.3036 | 0.6396 | 0.234* | 0.551 (15) |
H22B | 0.7033 | 0.3948 | 0.6264 | 0.234* | 0.551 (15) |
H22C | 0.7417 | 0.2849 | 0.6578 | 0.234* | 0.551 (15) |
H22D | 0.7337 | 0.3562 | 0.6805 | 0.234* | 0.449 (15) |
H22E | 0.6435 | 0.2477 | 0.6281 | 0.234* | 0.449 (15) |
H22F | 0.6287 | 0.3630 | 0.5972 | 0.234* | 0.449 (15) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N51 | 0.0675 (18) | 0.0601 (17) | 0.0762 (18) | 0.0068 (13) | 0.0161 (14) | 0.0082 (14) |
N52 | 0.079 (2) | 0.076 (2) | 0.084 (2) | −0.0060 (16) | 0.0072 (16) | 0.0150 (16) |
C62 | 0.0607 (18) | 0.0594 (19) | 0.0574 (17) | 0.0051 (16) | 0.0107 (15) | 0.0158 (15) |
C63 | 0.0581 (19) | 0.062 (2) | 0.0640 (18) | 0.0078 (16) | 0.0137 (15) | 0.0157 (15) |
C64 | 0.062 (2) | 0.062 (2) | 0.067 (2) | 0.0093 (16) | 0.0119 (16) | 0.0221 (17) |
C65 | 0.062 (2) | 0.075 (2) | 0.079 (2) | 0.0145 (18) | 0.0149 (17) | 0.0161 (18) |
C66 | 0.078 (2) | 0.065 (2) | 0.080 (2) | 0.0148 (19) | 0.0171 (19) | 0.0058 (17) |
C67 | 0.0584 (19) | 0.070 (2) | 0.078 (2) | 0.0061 (17) | 0.0153 (17) | 0.0187 (18) |
C68 | 0.0574 (19) | 0.075 (2) | 0.078 (2) | 0.0047 (17) | 0.0111 (16) | 0.0268 (19) |
C69 | 0.0592 (19) | 0.061 (2) | 0.068 (2) | 0.0126 (16) | 0.0135 (16) | 0.0220 (16) |
C70 | 0.072 (2) | 0.074 (2) | 0.086 (2) | 0.0005 (19) | 0.0278 (19) | 0.021 (2) |
C71 | 0.095 (3) | 0.070 (2) | 0.075 (2) | −0.001 (2) | 0.023 (2) | 0.0092 (18) |
C72 | 0.071 (2) | 0.060 (2) | 0.078 (2) | 0.0041 (17) | 0.0116 (18) | 0.0211 (18) |
C73 | 0.0577 (19) | 0.074 (2) | 0.078 (2) | 0.0058 (17) | 0.0152 (17) | 0.0187 (18) |
C74 | 0.066 (2) | 0.074 (2) | 0.0626 (19) | 0.0104 (17) | 0.0148 (16) | 0.0183 (17) |
C75 | 0.077 (3) | 0.078 (3) | 0.112 (3) | −0.004 (2) | 0.010 (2) | 0.013 (2) |
C76 | 0.088 (3) | 0.143 (4) | 0.116 (4) | 0.015 (3) | 0.012 (3) | 0.031 (3) |
C77 | 0.136 (5) | 0.244 (7) | 0.129 (4) | 0.054 (5) | 0.048 (4) | 0.090 (4) |
C78 | 0.111 (4) | 0.143 (4) | 0.127 (4) | 0.051 (3) | 0.008 (3) | 0.013 (3) |
C79 | 0.116 (3) | 0.081 (3) | 0.092 (3) | −0.007 (2) | 0.003 (2) | 0.005 (2) |
C80 | 0.155 (12) | 0.068 (7) | 0.072 (9) | −0.022 (7) | 0.027 (7) | −0.027 (6) |
C81 | 0.092 (7) | 0.077 (8) | 0.106 (10) | 0.024 (5) | 0.028 (6) | 0.043 (7) |
C80' | 0.157 (15) | 0.073 (7) | 0.093 (8) | −0.045 (8) | 0.021 (7) | −0.014 (5) |
C81' | 0.239 (18) | 0.140 (12) | 0.116 (9) | −0.047 (12) | 0.019 (10) | 0.027 (8) |
C82 | 0.160 (5) | 0.121 (5) | 0.217 (7) | 0.027 (4) | 0.080 (5) | 0.045 (5) |
N1 | 0.078 (2) | 0.0578 (18) | 0.0829 (19) | 0.0096 (14) | 0.0091 (15) | 0.0232 (14) |
N2 | 0.0628 (17) | 0.074 (2) | 0.087 (2) | 0.0060 (15) | 0.0078 (15) | 0.0146 (16) |
C2 | 0.071 (2) | 0.059 (2) | 0.0589 (18) | 0.0041 (17) | 0.0089 (16) | 0.0185 (15) |
C3 | 0.075 (2) | 0.058 (2) | 0.068 (2) | 0.0038 (18) | 0.0135 (17) | 0.0142 (16) |
C4 | 0.066 (2) | 0.069 (2) | 0.0604 (19) | 0.0031 (17) | 0.0131 (15) | 0.0209 (16) |
C5 | 0.072 (2) | 0.072 (2) | 0.081 (2) | 0.0160 (19) | 0.0144 (18) | 0.0225 (19) |
C6 | 0.086 (3) | 0.060 (2) | 0.088 (2) | 0.011 (2) | 0.010 (2) | 0.0232 (18) |
C7 | 0.073 (2) | 0.076 (2) | 0.076 (2) | 0.0160 (19) | 0.0186 (18) | 0.0246 (19) |
C8 | 0.074 (2) | 0.077 (3) | 0.067 (2) | 0.0149 (19) | 0.0199 (17) | 0.0206 (18) |
C9 | 0.059 (2) | 0.079 (2) | 0.0615 (19) | 0.0100 (18) | 0.0165 (15) | 0.0183 (17) |
C10 | 0.079 (2) | 0.059 (2) | 0.081 (2) | 0.0086 (18) | 0.0194 (18) | 0.0155 (17) |
C11 | 0.067 (2) | 0.074 (2) | 0.087 (2) | 0.0110 (19) | 0.0130 (18) | 0.0176 (19) |
C12 | 0.065 (2) | 0.064 (2) | 0.0632 (19) | 0.0001 (17) | 0.0126 (16) | 0.0128 (16) |
C13 | 0.062 (2) | 0.070 (2) | 0.082 (2) | 0.0081 (18) | 0.0141 (17) | 0.0191 (18) |
C14 | 0.065 (2) | 0.073 (2) | 0.082 (2) | 0.0122 (19) | 0.0135 (17) | 0.0214 (18) |
C15 | 0.073 (2) | 0.092 (3) | 0.076 (2) | −0.0011 (19) | 0.0076 (18) | 0.0174 (19) |
C16 | 0.073 (2) | 0.086 (3) | 0.081 (2) | 0.0036 (19) | 0.0120 (19) | 0.0205 (19) |
C17 | 0.082 (3) | 0.116 (3) | 0.104 (3) | 0.021 (2) | 0.015 (2) | 0.043 (3) |
C18 | 0.114 (3) | 0.146 (4) | 0.110 (3) | 0.049 (3) | 0.030 (3) | 0.030 (3) |
C19 | 0.091 (3) | 0.073 (3) | 0.102 (3) | 0.002 (2) | 0.015 (2) | 0.017 (2) |
C20 | 0.171 (12) | 0.070 (7) | 0.102 (8) | −0.006 (7) | 0.025 (8) | −0.031 (5) |
C21 | 0.125 (10) | 0.29 (2) | 0.154 (14) | 0.069 (11) | 0.070 (9) | 0.108 (14) |
C21' | 0.126 (12) | 0.46 (3) | 0.077 (9) | −0.120 (16) | 0.038 (9) | −0.068 (13) |
C20' | 0.127 (13) | 0.114 (12) | 0.26 (2) | −0.097 (10) | 0.064 (14) | −0.101 (12) |
C22 | 0.167 (5) | 0.164 (5) | 0.134 (5) | 0.049 (4) | 0.051 (4) | 0.019 (4) |
N51—C66 | 1.330 (4) | N1—C6 | 1.325 (4) |
N51—C62 | 1.340 (4) | N1—C2 | 1.339 (4) |
N52—C72 | 1.378 (4) | N2—C12 | 1.387 (4) |
N52—C79 | 1.440 (4) | N2—C19 | 1.446 (4) |
N52—C75 | 1.447 (4) | N2—C15 | 1.469 (4) |
C62—C63 | 1.381 (4) | C2—C3 | 1.384 (4) |
C62—C62i | 1.498 (6) | C2—C2ii | 1.501 (6) |
C63—C64 | 1.391 (4) | C3—C4 | 1.395 (4) |
C63—H63 | 0.9300 | C3—H3 | 0.9300 |
C64—C65 | 1.378 (4) | C4—C5 | 1.389 (4) |
C64—C67 | 1.461 (4) | C4—C7 | 1.468 (4) |
C65—C66 | 1.375 (4) | C5—C6 | 1.369 (4) |
C65—H65 | 0.9300 | C5—H5 | 0.9300 |
C66—H66 | 0.9300 | C6—H6 | 0.9300 |
C67—C68 | 1.323 (4) | C7—C8 | 1.312 (4) |
C67—H67 | 0.9300 | C7—H7 | 0.9300 |
C68—C69 | 1.453 (4) | C8—C9 | 1.479 (4) |
C68—H68 | 0.9300 | C8—H8 | 0.9300 |
C69—C70 | 1.383 (4) | C9—C14 | 1.379 (4) |
C69—C74 | 1.392 (4) | C9—C10 | 1.389 (4) |
C70—C71 | 1.382 (4) | C10—C11 | 1.377 (4) |
C70—H70 | 0.9300 | C10—H10 | 0.9300 |
C71—C72 | 1.399 (4) | C11—C12 | 1.392 (4) |
C71—H71 | 0.9300 | C11—H11 | 0.9300 |
C72—C73 | 1.394 (4) | C12—C13 | 1.399 (4) |
C73—C74 | 1.368 (4) | C13—C14 | 1.367 (4) |
C73—H73 | 0.9300 | C13—H13 | 0.9300 |
C74—H74 | 0.9300 | C14—H14 | 0.9300 |
C75—C76 | 1.569 (5) | C15—C16 | 1.519 (4) |
C75—H75A | 0.9700 | C15—H15A | 0.9700 |
C75—H75B | 0.9700 | C15—H15B | 0.9700 |
C76—C77 | 1.389 (6) | C16—C17 | 1.515 (5) |
C76—H76A | 0.9700 | C16—H16A | 0.9700 |
C76—H76B | 0.9700 | C16—H16B | 0.9700 |
C77—C78 | 1.504 (6) | C17—C18 | 1.494 (5) |
C77—H77A | 0.9700 | C17—H17A | 0.9700 |
C77—H77B | 0.9700 | C17—H17B | 0.9700 |
C78—H78A | 0.9600 | C18—H18A | 0.9600 |
C78—H78B | 0.9600 | C18—H18B | 0.9600 |
C78—H78C | 0.9600 | C18—H18C | 0.9600 |
C79—C80 | 1.497 (9) | C19—C20 | 1.501 (8) |
C79—C80' | 1.582 (11) | C19—C20' | 1.534 (11) |
C79—H79A | 0.9700 | C19—H19A | 0.9700 |
C79—H79B | 0.9700 | C19—H19B | 0.9700 |
C79—H79C | 0.9700 | C19—H19C | 0.9700 |
C79—H79D | 0.9700 | C19—H19D | 0.9700 |
C80—C81 | 1.464 (11) | C20—C21 | 1.281 (13) |
C80—H80A | 0.9700 | C20—H20A | 0.9700 |
C80—H80B | 0.9700 | C20—H20B | 0.9700 |
C81—C82 | 1.611 (10) | C21—C22 | 1.589 (11) |
C81—H81A | 0.9700 | C21—H21A | 0.9700 |
C81—H81B | 0.9700 | C21—H21B | 0.9700 |
C80'—C81' | 1.490 (12) | C21'—C20' | 1.233 (12) |
C80'—H80C | 0.9700 | C21'—C22 | 1.559 (11) |
C80'—H80D | 0.9700 | C21'—H21C | 0.9700 |
C81'—C82 | 1.562 (12) | C21'—H21D | 0.9700 |
C81'—H81C | 0.9700 | C20'—H20C | 0.9700 |
C81'—H81D | 0.9700 | C20'—H20D | 0.9700 |
C82—H82A | 0.9600 | C22—H22A | 0.9600 |
C82—H82B | 0.9600 | C22—H22B | 0.9600 |
C82—H82C | 0.9600 | C22—H22C | 0.9600 |
C82—H82D | 0.9600 | C22—H22D | 0.9600 |
C82—H82E | 0.9600 | C22—H22E | 0.9600 |
C82—H82F | 0.9600 | C22—H22F | 0.9600 |
C66—N51—C62 | 115.7 (3) | C12—N2—C19 | 123.1 (3) |
C72—N52—C79 | 123.1 (3) | C12—N2—C15 | 120.4 (3) |
C72—N52—C75 | 120.7 (3) | C19—N2—C15 | 116.5 (3) |
C79—N52—C75 | 115.6 (3) | N1—C2—C3 | 123.1 (3) |
N51—C62—C63 | 123.2 (3) | N1—C2—C2ii | 115.9 (3) |
N51—C62—C62i | 116.2 (3) | C3—C2—C2ii | 121.0 (4) |
C63—C62—C62i | 120.5 (4) | C2—C3—C4 | 119.9 (3) |
C62—C63—C64 | 120.2 (3) | C2—C3—H3 | 120.1 |
C62—C63—H63 | 119.9 | C4—C3—H3 | 120.1 |
C64—C63—H63 | 119.9 | C5—C4—C3 | 116.4 (3) |
C65—C64—C63 | 116.4 (3) | C5—C4—C7 | 119.6 (3) |
C65—C64—C67 | 120.6 (3) | C3—C4—C7 | 124.0 (3) |
C63—C64—C67 | 122.9 (3) | C6—C5—C4 | 119.5 (3) |
C66—C65—C64 | 119.4 (3) | C6—C5—H5 | 120.2 |
C66—C65—H65 | 120.3 | C4—C5—H5 | 120.2 |
C64—C65—H65 | 120.3 | N1—C6—C5 | 124.7 (3) |
N51—C66—C65 | 125.0 (3) | N1—C6—H6 | 117.6 |
N51—C66—H66 | 117.5 | C5—C6—H6 | 117.6 |
C65—C66—H66 | 117.5 | C8—C7—C4 | 126.5 (3) |
C68—C67—C64 | 125.3 (3) | C8—C7—H7 | 116.7 |
C68—C67—H67 | 117.3 | C4—C7—H7 | 116.7 |
C64—C67—H67 | 117.3 | C7—C8—C9 | 127.9 (3) |
C67—C68—C69 | 128.5 (3) | C7—C8—H8 | 116.0 |
C67—C68—H68 | 115.7 | C9—C8—H8 | 116.0 |
C69—C68—H68 | 115.7 | C14—C9—C10 | 116.1 (3) |
C70—C69—C74 | 115.1 (3) | C14—C9—C8 | 120.7 (3) |
C70—C69—C68 | 120.8 (3) | C10—C9—C8 | 123.2 (3) |
C74—C69—C68 | 124.1 (3) | C11—C10—C9 | 121.6 (3) |
C71—C70—C69 | 123.4 (3) | C11—C10—H10 | 119.2 |
C71—C70—H70 | 118.3 | C9—C10—H10 | 119.2 |
C69—C70—H70 | 118.3 | C10—C11—C12 | 121.8 (3) |
C70—C71—C72 | 120.8 (3) | C10—C11—H11 | 119.1 |
C70—C71—H71 | 119.6 | C12—C11—H11 | 119.1 |
C72—C71—H71 | 119.6 | N2—C12—C11 | 121.6 (3) |
N52—C72—C73 | 123.1 (3) | N2—C12—C13 | 122.1 (3) |
N52—C72—C71 | 121.0 (3) | C11—C12—C13 | 116.3 (3) |
C73—C72—C71 | 115.9 (3) | C14—C13—C12 | 120.9 (3) |
C74—C73—C72 | 122.2 (3) | C14—C13—H13 | 119.6 |
C74—C73—H73 | 118.9 | C12—C13—H13 | 119.6 |
C72—C73—H73 | 118.9 | C13—C14—C9 | 123.2 (3) |
C73—C74—C69 | 122.4 (3) | C13—C14—H14 | 118.4 |
C73—C74—H74 | 118.8 | C9—C14—H14 | 118.4 |
C69—C74—H74 | 118.8 | N2—C15—C16 | 113.5 (3) |
N52—C75—C76 | 110.9 (3) | N2—C15—H15A | 108.9 |
N52—C75—H75A | 109.5 | C16—C15—H15A | 108.9 |
C76—C75—H75A | 109.5 | N2—C15—H15B | 108.9 |
N52—C75—H75B | 109.5 | C16—C15—H15B | 108.9 |
C76—C75—H75B | 109.5 | H15A—C15—H15B | 107.7 |
H75A—C75—H75B | 108.1 | C17—C16—C15 | 111.8 (3) |
C77—C76—C75 | 113.8 (4) | C17—C16—H16A | 109.3 |
C77—C76—H76A | 108.8 | C15—C16—H16A | 109.3 |
C75—C76—H76A | 108.8 | C17—C16—H16B | 109.3 |
C77—C76—H76B | 108.8 | C15—C16—H16B | 109.3 |
C75—C76—H76B | 108.8 | H16A—C16—H16B | 107.9 |
H76A—C76—H76B | 107.7 | C18—C17—C16 | 112.8 (3) |
C76—C77—C78 | 117.7 (5) | C18—C17—H17A | 109.0 |
C76—C77—H77A | 107.9 | C16—C17—H17A | 109.0 |
C78—C77—H77A | 107.9 | C18—C17—H17B | 109.0 |
C76—C77—H77B | 107.9 | C16—C17—H17B | 109.0 |
C78—C77—H77B | 107.9 | H17A—C17—H17B | 107.8 |
H77A—C77—H77B | 107.2 | C17—C18—H18A | 109.5 |
C77—C78—H78A | 109.5 | C17—C18—H18B | 109.5 |
C77—C78—H78B | 109.5 | H18A—C18—H18B | 109.5 |
H78A—C78—H78B | 109.5 | C17—C18—H18C | 109.5 |
C77—C78—H78C | 109.5 | H18A—C18—H18C | 109.5 |
H78A—C78—H78C | 109.5 | H18B—C18—H18C | 109.5 |
H78B—C78—H78C | 109.5 | N2—C19—C20 | 121.3 (5) |
N52—C79—C80 | 124.8 (6) | N2—C19—C20' | 103.4 (8) |
N52—C79—C80' | 99.6 (5) | N2—C19—H19A | 107.0 |
N52—C79—H79A | 106.1 | C20—C19—H19A | 107.0 |
C80—C79—H79A | 106.1 | N2—C19—H19B | 107.0 |
N52—C79—H79B | 106.1 | C20—C19—H19B | 107.0 |
C80—C79—H79B | 106.1 | H19A—C19—H19B | 106.7 |
H79A—C79—H79B | 106.3 | N2—C19—H19C | 111.1 |
N52—C79—H79C | 111.8 | C20—C19—H19C | 117.4 |
C80'—C79—H79C | 111.8 | C20'—C19—H19C | 111.1 |
N52—C79—H79D | 111.8 | N2—C19—H19D | 111.1 |
C80'—C79—H79D | 111.8 | C20'—C19—H19D | 111.1 |
H79C—C79—H79D | 109.6 | H19C—C19—H19D | 109.0 |
C81—C80—C79 | 111.3 (9) | C21—C20—C19 | 121.4 (11) |
C81—C80—H80A | 109.4 | C21—C20—H20A | 107.0 |
C79—C80—H80A | 109.4 | C19—C20—H20A | 107.0 |
C81—C80—H80B | 109.4 | C21—C20—H20B | 107.0 |
C79—C80—H80B | 109.4 | C19—C20—H20B | 107.0 |
H80A—C80—H80B | 108.0 | H20A—C20—H20B | 106.7 |
C80—C81—C82 | 108.9 (8) | C20—C21—C22 | 117.2 (11) |
C80—C81—H81A | 109.9 | C20—C21—H21A | 108.0 |
C82—C81—H81A | 109.9 | C22—C21—H21A | 108.0 |
C80—C81—H81B | 109.9 | C20—C21—H21B | 108.0 |
C82—C81—H81B | 109.9 | C22—C21—H21B | 108.0 |
H81A—C81—H81B | 108.3 | H21A—C21—H21B | 107.2 |
C81'—C80'—C79 | 111.4 (9) | C20'—C21'—C22 | 119.6 (11) |
C81'—C80'—H80C | 109.3 | C20'—C21'—H21C | 107.4 |
C79—C80'—H80C | 109.3 | C22—C21'—H21C | 107.4 |
C81'—C80'—H80D | 109.3 | C20'—C21'—H21D | 107.4 |
C79—C80'—H80D | 109.3 | C22—C21'—H21D | 107.4 |
H80C—C80'—H80D | 108.0 | H21C—C21'—H21D | 107.0 |
C80'—C81'—C82 | 104.1 (9) | C21'—C20'—C19 | 124.0 (10) |
C80'—C81'—H81C | 110.9 | C21'—C20'—H20C | 106.3 |
C82—C81'—H81C | 110.9 | C19—C20'—H20C | 106.3 |
C80'—C81'—H81D | 110.9 | C21'—C20'—H20D | 106.3 |
C82—C81'—H81D | 110.9 | C19—C20'—H20D | 106.3 |
H81C—C81'—H81D | 109.0 | H20C—C20'—H20D | 106.4 |
C81—C82—H82A | 109.5 | C21—C22—H22A | 109.5 |
C81—C82—H82B | 109.5 | C21—C22—H22B | 109.5 |
H82A—C82—H82B | 109.5 | H22A—C22—H22B | 109.5 |
C81'—C82—H82C | 70.8 | C21—C22—H22C | 109.5 |
C81'—C82—H82D | 109.5 | H22A—C22—H22C | 109.5 |
C81'—C82—H82E | 109.5 | H22B—C22—H22C | 109.5 |
C81—C82—H82E | 74.2 | C21'—C22—H22D | 109.5 |
H82D—C82—H82E | 109.5 | C21'—C22—H22E | 109.5 |
C81'—C82—H82F | 109.5 | H22D—C22—H22E | 109.5 |
H82D—C82—H82F | 109.5 | C21'—C22—H22F | 109.5 |
H82E—C82—H82F | 109.5 | H22D—C22—H22F | 109.5 |
C6—N1—C2 | 116.4 (3) | H22E—C22—H22F | 109.5 |
C66—N51—C62—C63 | −0.5 (4) | C6—N1—C2—C3 | 0.9 (4) |
C66—N51—C62—C62i | 179.9 (3) | C6—N1—C2—C2ii | −179.3 (3) |
N51—C62—C63—C64 | 0.4 (5) | N1—C2—C3—C4 | −1.6 (5) |
C62i—C62—C63—C64 | 179.9 (3) | C2ii—C2—C3—C4 | 178.5 (3) |
C62—C63—C64—C65 | 0.9 (4) | C2—C3—C4—C5 | 1.0 (4) |
C62—C63—C64—C67 | −178.6 (3) | C2—C3—C4—C7 | −178.8 (3) |
C63—C64—C65—C66 | −2.0 (5) | C3—C4—C5—C6 | 0.3 (5) |
C67—C64—C65—C66 | 177.5 (3) | C7—C4—C5—C6 | −179.9 (3) |
C62—N51—C66—C65 | −0.7 (5) | C2—N1—C6—C5 | 0.5 (5) |
C64—C65—C66—N51 | 2.1 (5) | C4—C5—C6—N1 | −1.1 (5) |
C65—C64—C67—C68 | −155.0 (3) | C5—C4—C7—C8 | 167.0 (3) |
C63—C64—C67—C68 | 24.5 (5) | C3—C4—C7—C8 | −13.3 (5) |
C64—C67—C68—C69 | 179.4 (3) | C4—C7—C8—C9 | 179.3 (3) |
C67—C68—C69—C70 | −168.0 (3) | C7—C8—C9—C14 | 179.8 (3) |
C67—C68—C69—C74 | 11.9 (5) | C7—C8—C9—C10 | −1.6 (5) |
C74—C69—C70—C71 | −2.8 (5) | C14—C9—C10—C11 | −0.3 (5) |
C68—C69—C70—C71 | 177.1 (3) | C8—C9—C10—C11 | −179.0 (3) |
C69—C70—C71—C72 | −0.5 (5) | C9—C10—C11—C12 | 2.3 (5) |
C79—N52—C72—C73 | −168.9 (3) | C19—N2—C12—C11 | 176.4 (3) |
C75—N52—C72—C73 | 1.5 (5) | C15—N2—C12—C11 | −5.3 (5) |
C79—N52—C72—C71 | 12.4 (5) | C19—N2—C12—C13 | −4.3 (5) |
C75—N52—C72—C71 | −177.2 (3) | C15—N2—C12—C13 | 174.0 (3) |
C70—C71—C72—N52 | −177.5 (3) | C10—C11—C12—N2 | 176.2 (3) |
C70—C71—C72—C73 | 3.8 (5) | C10—C11—C12—C13 | −3.1 (5) |
N52—C72—C73—C74 | 177.5 (3) | N2—C12—C13—C14 | −177.2 (3) |
C71—C72—C73—C74 | −3.8 (5) | C11—C12—C13—C14 | 2.1 (5) |
C72—C73—C74—C69 | 0.5 (5) | C12—C13—C14—C9 | −0.3 (5) |
C70—C69—C74—C73 | 2.8 (4) | C10—C9—C14—C13 | −0.7 (5) |
C68—C69—C74—C73 | −177.1 (3) | C8—C9—C14—C13 | 178.1 (3) |
C72—N52—C75—C76 | −82.7 (4) | C12—N2—C15—C16 | 84.7 (4) |
C79—N52—C75—C76 | 88.4 (4) | C19—N2—C15—C16 | −96.8 (4) |
N52—C75—C76—C77 | 173.8 (4) | N2—C15—C16—C17 | −170.5 (3) |
C75—C76—C77—C78 | −176.4 (4) | C15—C16—C17—C18 | −179.1 (3) |
C72—N52—C79—C80 | −110.7 (7) | C12—N2—C19—C20 | 105.6 (7) |
C75—N52—C79—C80 | 78.5 (7) | C15—N2—C19—C20 | −72.8 (7) |
C72—N52—C79—C80' | −89.7 (6) | C12—N2—C19—C20' | 80.6 (8) |
C75—N52—C79—C80' | 99.4 (6) | C15—N2—C19—C20' | −97.9 (8) |
N52—C79—C80—C81 | 74.5 (12) | N2—C19—C20—C21 | −70.9 (14) |
C80'—C79—C80—C81 | 32.3 (11) | C20'—C19—C20—C21 | −13 (2) |
C79—C80—C81—C82 | −179.6 (7) | C19—C20—C21—C22 | 172.9 (8) |
N52—C79—C80'—C81' | −178.7 (10) | C22—C21'—C20'—C19 | 168.7 (15) |
C80—C79—C80'—C81' | −32.7 (12) | N2—C19—C20'—C21' | 119 (3) |
C79—C80'—C81'—C82 | −178.1 (8) | C20—C19—C20'—C21' | −13.0 (18) |
C80'—C81'—C82—C81 | 31.6 (8) | C20'—C21'—C22—C21 | −7.7 (18) |
C80—C81—C82—C81' | −34.2 (10) | C20—C21—C22—C21' | −11.1 (17) |
Symmetry codes: (i) −x, −y, −z; (ii) −x, −y−1, −z. |
P1 | P1 | |
reflections | 7957 | 8401 |
parameters | 453 | 820 |
R[F2 > 2σ(F2)] | 0.0795 | 0.0776 |
wR(F2) | 0.2702 | 0.3179 |
S | 1.023 | 0.928 |
(Δ/σ)max | <0.001 | 0.851 |
N1-C2 | 1.325 (4) | 1.366 (13) |
N1-C6 | 1.325 (4) | 1.295 (14) |
N3-C32 | - | 1.311 (12) |
N3-C36 | - | 1.383 (15) |
N51-C62 | 1.340 (4) | 1.349 (12) |
N51-C66 | 1.330 (4) | 1.315 (14) |
N53-C92 | - | 1.324 (12) |
N53-C92 | - | 1.353 (14) |
C6-N1-C2 | 116.4 (3) | 114.0 (9) |
C32-N3-C36 | - | 119.4 (9) |
C66-N51-C62 | 115.7 (3) | 116.0 (8) |
C92-N53-C96 | - | 115.8 (9) |