Acta Cryst. (2007). E63, o3968 [ doi:10.1107/S1600536807042559 ]
In the title compound, C18H26ClN5, there are four molecules in the asymmetric unit, two of which show disorder of their tert-butyl groups in 0.58 (2):0.42 (2) and 0.753 (4):0.247 (4) ratios. A complex network of N-H
N hydrogen bonds helps to establish the packing.
The title compound was prepared according to the method of Kaiser & Thurston (1951). 2,4,6-Trichloro-1,3,5-triazine (20.0 g, 0.109 mol) was dissolved in toluene (65 ml) and then cooled to 278 K. With stirring, a solution of 2,4,4-trimethylpentan-2-amine (13.75 g, 0.107 mol) in toluene (35 ml) was then added dropwise to the mixture over a period of 30 min. Then, a solution of Na2CO3 (11.51 g, 0.109 mol) in water (30 ml) was then added dropwise for 30 min. The mixture was stirred at 273–278 K for a further 3 h and phenylmethanamine (11.61 g, 0.109 mol) and solid Na2CO3 (11.51 g, 0.109 mol) were added to the mixture, maintaining the temperature at 358 K for 4.5 h. The organic layer was washed with water and then concentrated in vacuo. The title compound (28.47 g) was obtained in powder form in a yield of 75.4%. Colourles blocks (I) were obtained by slow evaporation of a solution of methanol (m.p. 421–423 K).
The N-bound H atoms were located in a difference map and their positions and Uiso values were freely refined.
The C-bound H atoms were positioned geometrically (C—H = 0.98–0.99 Å), and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).
Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1996); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).
![[Figure 1]](./hb2528fig1thm.gif)
| Fig. 1. A view of the structure of the Cl2 molecule in (I). Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii. |
| C18H26ClN5 | Z = 8 |
| Mr = 347.89 | F000 = 1488 |
| Triclinic, P1 | Dx = 1.206 Mg m−3 |
| Hall symbol: -P 1 | Melting point: 421-423 K |
| a = 8.0987 (16) Å | Mo Kα radiation λ = 0.71073 Å |
| b = 20.811 (4) Å | Cell parameters from 8593 reflections |
| c = 23.984 (5) Å | θ = 1.8–27.9º |
| α = 105.36 (3)º | µ = 0.21 mm−1 |
| β = 96.33 (3)º | T = 113 (2) K |
| γ = 96.46 (3)º | Block, colorless |
| V = 3831.6 (13) Å3 | 0.34 × 0.32 × 0.18 mm |
| Rigaku Saturn diffractometer | 17590 independent reflections |
| Radiation source: rotating anode | 14508 reflections with I > 2σ(I) |
| Monochromator: confocal | Rint = 0.035 |
| T = 113(2) K | θmax = 27.8º |
| ω scans | θmin = 1.5º |
| Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) | h = −10→10 |
| Tmin = 0.932, Tmax = 0.963 | k = −27→27 |
| 35937 measured reflections | l = −31→31 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.056 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.134 | w = 1/[σ2(Fo2) + (0.0532P)2 + 1.4707P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.08 | (Δ/σ)max = 0.001 |
| 17590 reflections | Δρmax = 0.55 e Å−3 |
| 979 parameters | Δρmin = −0.53 e Å−3 |
| 96 restraints | Extinction correction: none |
| Primary atom site location: structure-invariant direct methods |
| C18H26ClN5 | γ = 96.46 (3)º |
| Mr = 347.89 | V = 3831.6 (13) Å3 |
| Triclinic, P1 | Z = 8 |
| a = 8.0987 (16) Å | Mo Kα |
| b = 20.811 (4) Å | µ = 0.21 mm−1 |
| c = 23.984 (5) Å | T = 113 (2) K |
| α = 105.36 (3)º | 0.34 × 0.32 × 0.18 mm |
| β = 96.33 (3)º |
| Rigaku Saturn diffractometer | 17590 independent reflections |
| Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) | 14508 reflections with I > 2σ(I) |
| Tmin = 0.932, Tmax = 0.963 | Rint = 0.035 |
| 35937 measured reflections |
| R[F2 > 2σ(F2)] = 0.056 | 96 restraints |
| wR(F2) = 0.134 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.08 | Δρmax = 0.55 e Å−3 |
| 17590 reflections | Δρmin = −0.53 e Å−3 |
| 979 parameters |
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 > 2sigma(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) | |
| Cl1 | 0.25176 (6) | 0.22828 (2) | 0.156778 (19) | 0.02256 (11) | |
| N1 | 0.51718 (18) | 0.39243 (7) | 0.10231 (6) | 0.0168 (3) | |
| N2 | 0.45024 (19) | 0.34162 (7) | 0.17781 (6) | 0.0177 (3) | |
| N3 | 0.33144 (18) | 0.28719 (7) | 0.07868 (6) | 0.0165 (3) | |
| N4 | 0.61749 (19) | 0.44332 (7) | 0.20073 (7) | 0.0180 (3) | |
| N5 | 0.3981 (2) | 0.33659 (8) | 0.00755 (7) | 0.0188 (3) | |
| C1 | 0.5267 (2) | 0.39225 (9) | 0.15850 (7) | 0.0161 (4) | |
| C2 | 0.3578 (2) | 0.29361 (9) | 0.13527 (7) | 0.0165 (4) | |
| C3 | 0.4182 (2) | 0.33940 (9) | 0.06421 (7) | 0.0160 (3) | |
| C4 | 0.7199 (2) | 0.50406 (9) | 0.19479 (8) | 0.0189 (4) | |
| C5 | 0.8540 (2) | 0.48759 (9) | 0.15411 (8) | 0.0206 (4) | |
| H5A | 0.9110 | 0.5314 | 0.1520 | 0.025* | |
| H5B | 0.7919 | 0.4646 | 0.1146 | 0.025* | |
| C6 | 0.9950 (2) | 0.44549 (10) | 0.16437 (8) | 0.0239 (4) | |
| C7 | 0.7949 (3) | 0.54427 (10) | 0.25749 (8) | 0.0265 (4) | |
| H7A | 0.7045 | 0.5594 | 0.2794 | 0.040* | |
| H7B | 0.8729 | 0.5835 | 0.2568 | 0.040* | |
| H7C | 0.8552 | 0.5156 | 0.2764 | 0.040* | |
| C8 | 0.6039 (3) | 0.54624 (10) | 0.16903 (9) | 0.0266 (4) | |
| H8A | 0.5523 | 0.5206 | 0.1293 | 0.040* | |
| H8B | 0.6699 | 0.5882 | 0.1679 | 0.040* | |
| H8C | 0.5158 | 0.5567 | 0.1935 | 0.040* | |
| C9 | 1.111 (2) | 0.4693 (7) | 0.2234 (4) | 0.056 (4) | 0.42 (2) |
| H9A | 1.0492 | 0.4596 | 0.2539 | 0.084* | 0.42 (2) |
| H9B | 1.1479 | 0.5179 | 0.2328 | 0.084* | 0.42 (2) |
| H9C | 1.2086 | 0.4455 | 0.2210 | 0.084* | 0.42 (2) |
| C10 | 0.9190 (13) | 0.3714 (4) | 0.1544 (9) | 0.043 (3) | 0.42 (2) |
| H10A | 1.0095 | 0.3439 | 0.1542 | 0.065* | 0.42 (2) |
| H10B | 0.8450 | 0.3555 | 0.1168 | 0.065* | 0.42 (2) |
| H10C | 0.8541 | 0.3679 | 0.1859 | 0.065* | 0.42 (2) |
| C11 | 1.108 (2) | 0.4471 (9) | 0.1174 (6) | 0.043 (3) | 0.42 (2) |
| H11A | 1.1943 | 0.4182 | 0.1202 | 0.064* | 0.42 (2) |
| H11B | 1.1621 | 0.4935 | 0.1233 | 0.064* | 0.42 (2) |
| H11C | 1.0401 | 0.4308 | 0.0786 | 0.064* | 0.42 (2) |
| C9' | 1.1350 (11) | 0.4899 (6) | 0.2119 (5) | 0.065 (3) | 0.58 (2) |
| H9'1 | 1.0931 | 0.5009 | 0.2495 | 0.097* | 0.58 (2) |
| H9'2 | 1.1703 | 0.5315 | 0.2018 | 0.097* | 0.58 (2) |
| H9'3 | 1.2310 | 0.4655 | 0.2145 | 0.097* | 0.58 (2) |
| C10' | 0.9370 (13) | 0.3817 (5) | 0.1808 (5) | 0.049 (2) | 0.58 (2) |
| H10D | 0.8428 | 0.3547 | 0.1517 | 0.073* | 0.58 (2) |
| H10E | 0.9008 | 0.3938 | 0.2194 | 0.073* | 0.58 (2) |
| H10F | 1.0299 | 0.3554 | 0.1817 | 0.073* | 0.58 (2) |
| C11' | 1.0693 (14) | 0.4258 (6) | 0.1073 (3) | 0.0358 (18) | 0.58 (2) |
| H11D | 1.1653 | 0.4022 | 0.1129 | 0.054* | 0.58 (2) |
| H11E | 1.1064 | 0.4665 | 0.0961 | 0.054* | 0.58 (2) |
| H11F | 0.9836 | 0.3961 | 0.0764 | 0.054* | 0.58 (2) |
| C12 | 0.4864 (2) | 0.38653 (9) | −0.01533 (8) | 0.0198 (4) | |
| H12A | 0.4994 | 0.4311 | 0.0139 | 0.024* | |
| H12B | 0.4166 | 0.3892 | −0.0510 | 0.024* | |
| C13 | 0.6584 (2) | 0.37214 (9) | −0.03011 (8) | 0.0199 (4) | |
| C14 | 0.7036 (3) | 0.30838 (11) | −0.03965 (10) | 0.0302 (5) | |
| H14A | 0.6266 | 0.2723 | −0.0359 | 0.036* | |
| C15 | 0.8611 (3) | 0.29648 (12) | −0.05476 (10) | 0.0365 (5) | |
| H15A | 0.8909 | 0.2525 | −0.0610 | 0.044* | |
| C16 | 0.9740 (3) | 0.34835 (12) | −0.06067 (9) | 0.0327 (5) | |
| H16 | 1.0815 | 0.3403 | −0.0708 | 0.039* | |
| C17 | 0.9296 (3) | 0.41180 (12) | −0.05183 (10) | 0.0348 (5) | |
| H17 | 1.0066 | 0.4475 | −0.0561 | 0.042* | |
| C18 | 0.7725 (3) | 0.42401 (11) | −0.03661 (9) | 0.0299 (5) | |
| H18 | 0.7431 | 0.4680 | −0.0306 | 0.036* | |
| Cl2 | 0.41948 (6) | 0.53961 (2) | 0.346225 (19) | 0.02303 (11) | |
| N6 | 0.60553 (19) | 0.36615 (7) | 0.39037 (6) | 0.0179 (3) | |
| N7 | 0.54407 (19) | 0.42739 (7) | 0.32025 (6) | 0.0184 (3) | |
| N8 | 0.49763 (19) | 0.47124 (7) | 0.41881 (6) | 0.0178 (3) | |
| N9 | 0.6442 (2) | 0.32725 (8) | 0.29300 (7) | 0.0194 (3) | |
| N10 | 0.5585 (2) | 0.41230 (8) | 0.48486 (7) | 0.0196 (3) | |
| C19 | 0.5968 (2) | 0.37354 (9) | 0.33635 (7) | 0.0167 (4) | |
| C20 | 0.4964 (2) | 0.47114 (9) | 0.36373 (8) | 0.0172 (4) | |
| C21 | 0.5555 (2) | 0.41615 (9) | 0.43003 (7) | 0.0166 (4) | |
| C22 | 0.6925 (2) | 0.26095 (9) | 0.29462 (8) | 0.0198 (4) | |
| C23 | 0.8450 (2) | 0.26562 (10) | 0.34155 (8) | 0.0218 (4) | |
| H23A | 0.8066 | 0.2822 | 0.3799 | 0.026* | |
| H23B | 0.8645 | 0.2187 | 0.3381 | 0.026* | |
| C24 | 1.0196 (2) | 0.30679 (11) | 0.34632 (9) | 0.0275 (4) | |
| C25 | 0.7218 (3) | 0.22687 (10) | 0.23221 (8) | 0.0276 (4) | |
| H25A | 0.6154 | 0.2173 | 0.2057 | 0.041* | |
| H25B | 0.7656 | 0.1846 | 0.2312 | 0.041* | |
| H25C | 0.8031 | 0.2569 | 0.2198 | 0.041* | |
| C26 | 0.5431 (2) | 0.21836 (10) | 0.30844 (9) | 0.0262 (4) | |
| H26A | 0.5190 | 0.2401 | 0.3476 | 0.039* | |
| H26B | 0.5707 | 0.1733 | 0.3069 | 0.039* | |
| H26C | 0.4442 | 0.2145 | 0.2796 | 0.039* | |
| C27 | 1.1306 (3) | 0.29118 (16) | 0.39577 (12) | 0.0548 (8) | |
| H27A | 1.1360 | 0.2427 | 0.3858 | 0.082* | |
| H27B | 1.0828 | 0.3048 | 0.4322 | 0.082* | |
| H27C | 1.2441 | 0.3160 | 0.4009 | 0.082* | |
| C28 | 1.0154 (3) | 0.38242 (12) | 0.36303 (14) | 0.0533 (7) | |
| H28A | 1.1303 | 0.4065 | 0.3703 | 0.080* | |
| H28B | 0.9629 | 0.3955 | 0.3985 | 0.080* | |
| H28C | 0.9503 | 0.3940 | 0.3311 | 0.080* | |
| C29 | 1.1032 (3) | 0.28702 (15) | 0.29119 (11) | 0.0500 (7) | |
| H29A | 1.0451 | 0.3026 | 0.2603 | 0.075* | |
| H29B | 1.0968 | 0.2379 | 0.2781 | 0.075* | |
| H29C | 1.2212 | 0.3079 | 0.2999 | 0.075* | |
| C30 | 0.6211 (2) | 0.35846 (9) | 0.50476 (8) | 0.0195 (4) | |
| H30A | 0.5938 | 0.3163 | 0.4724 | 0.023* | |
| H30B | 0.5615 | 0.3518 | 0.5371 | 0.023* | |
| C31 | 0.8088 (2) | 0.37065 (9) | 0.52564 (8) | 0.0204 (4) | |
| C32 | 0.8865 (3) | 0.31716 (11) | 0.53284 (11) | 0.0358 (5) | |
| H32 | 0.8220 | 0.2737 | 0.5235 | 0.043* | |
| C33 | 1.0568 (3) | 0.32539 (13) | 0.55349 (11) | 0.0403 (6) | |
| H33 | 1.1073 | 0.2878 | 0.5585 | 0.048* | |
| C34 | 1.1519 (3) | 0.38748 (13) | 0.56667 (11) | 0.0426 (6) | |
| H34 | 1.2688 | 0.3935 | 0.5802 | 0.051* | |
| C35 | 1.0751 (3) | 0.44103 (14) | 0.55990 (16) | 0.0713 (11) | |
| H35 | 1.1399 | 0.4845 | 0.5692 | 0.086* | |
| C36 | 0.9044 (3) | 0.43288 (12) | 0.53970 (14) | 0.0537 (8) | |
| H36 | 0.8537 | 0.4707 | 0.5356 | 0.064* | |
| Cl3 | 1.14070 (7) | −0.03951 (2) | 0.64751 (2) | 0.02864 (12) | |
| N11 | 0.90224 (19) | 0.12914 (7) | 0.61493 (6) | 0.0176 (3) | |
| N12 | 1.01421 (19) | 0.07117 (8) | 0.68179 (6) | 0.0197 (3) | |
| N13 | 1.01909 (19) | 0.02732 (8) | 0.57954 (6) | 0.0189 (3) | |
| N14 | 0.9165 (2) | 0.17138 (8) | 0.71538 (7) | 0.0210 (3) | |
| N15 | 0.9065 (2) | 0.08231 (8) | 0.51668 (6) | 0.0187 (3) | |
| C37 | 0.9436 (2) | 0.12389 (9) | 0.66904 (7) | 0.0176 (4) | |
| C38 | 1.0467 (2) | 0.02792 (9) | 0.63493 (8) | 0.0191 (4) | |
| C39 | 0.9421 (2) | 0.08014 (9) | 0.57184 (7) | 0.0168 (4) | |
| C40 | 0.8286 (2) | 0.23066 (9) | 0.71594 (8) | 0.0210 (4) | |
| C41 | 0.6431 (2) | 0.20115 (9) | 0.68843 (8) | 0.0206 (4) | |
| H41A | 0.6479 | 0.1647 | 0.6527 | 0.025* | |
| H41B | 0.5947 | 0.1792 | 0.7161 | 0.025* | |
| C42 | 0.5123 (2) | 0.24412 (9) | 0.67094 (8) | 0.0227 (4) | |
| C43 | 0.9193 (2) | 0.27622 (10) | 0.68524 (9) | 0.0250 (4) | |
| H43A | 1.0387 | 0.2868 | 0.7017 | 0.038* | |
| H43B | 0.8702 | 0.3180 | 0.6908 | 0.038* | |
| H43C | 0.9076 | 0.2532 | 0.6434 | 0.038* | |
| C44 | 0.8433 (3) | 0.26835 (10) | 0.78098 (8) | 0.0303 (5) | |
| H44A | 0.7858 | 0.2393 | 0.8013 | 0.045* | |
| H44B | 0.7913 | 0.3094 | 0.7852 | 0.045* | |
| H44C | 0.9621 | 0.2804 | 0.7980 | 0.045* | |
| C45 | 0.5010 (3) | 0.30788 (10) | 0.71917 (9) | 0.0318 (5) | |
| H45A | 0.6040 | 0.3400 | 0.7252 | 0.048* | |
| H45B | 0.4877 | 0.2962 | 0.7556 | 0.048* | |
| H45C | 0.4042 | 0.3283 | 0.7076 | 0.048* | |
| C46 | 0.3414 (3) | 0.19809 (11) | 0.65819 (11) | 0.0350 (5) | |
| H46A | 0.3152 | 0.1879 | 0.6941 | 0.052* | |
| H46B | 0.3469 | 0.1561 | 0.6284 | 0.052* | |
| H46C | 0.2537 | 0.2211 | 0.6439 | 0.052* | |
| C47 | 0.5413 (3) | 0.26333 (11) | 0.61505 (9) | 0.0291 (5) | |
| H47A | 0.4463 | 0.2840 | 0.6024 | 0.044* | |
| H47B | 0.5512 | 0.2228 | 0.5843 | 0.044* | |
| H47C | 0.6449 | 0.2955 | 0.6227 | 0.044* | |
| C48 | 0.8381 (2) | 0.13786 (9) | 0.50105 (8) | 0.0192 (4) | |
| H48A | 0.8927 | 0.1473 | 0.4685 | 0.023* | |
| H48B | 0.8674 | 0.1785 | 0.5349 | 0.023* | |
| C49 | 0.6487 (2) | 0.12544 (9) | 0.48282 (8) | 0.0198 (4) | |
| C50 | 0.5413 (3) | 0.08988 (10) | 0.50896 (9) | 0.0246 (4) | |
| H50 | 0.5864 | 0.0701 | 0.5376 | 0.029* | |
| C51 | 0.3679 (3) | 0.08275 (10) | 0.49370 (10) | 0.0297 (5) | |
| H51 | 0.2954 | 0.0582 | 0.5118 | 0.036* | |
| C52 | 0.3012 (3) | 0.11149 (12) | 0.45208 (11) | 0.0360 (5) | |
| H52 | 0.1829 | 0.1072 | 0.4420 | 0.043* | |
| C53 | 0.4066 (3) | 0.14630 (13) | 0.42534 (11) | 0.0400 (6) | |
| H53 | 0.3610 | 0.1656 | 0.3965 | 0.048* | |
| C54 | 0.5797 (3) | 0.15324 (11) | 0.44046 (9) | 0.0298 (5) | |
| H54 | 0.6517 | 0.1772 | 0.4217 | 0.036* | |
| Cl4 | −0.31144 (6) | 0.73479 (2) | 0.15285 (2) | 0.02536 (11) | |
| N16 | −0.04068 (19) | 0.89942 (7) | 0.10058 (6) | 0.0178 (3) | |
| N17 | −0.11611 (19) | 0.84876 (8) | 0.17520 (6) | 0.0189 (3) | |
| N18 | −0.22056 (19) | 0.79254 (7) | 0.07524 (6) | 0.0175 (3) | |
| N19 | 0.0458 (2) | 0.95158 (8) | 0.19963 (7) | 0.0206 (3) | |
| N20 | −0.1436 (2) | 0.84117 (8) | 0.00481 (6) | 0.0186 (3) | |
| C55 | −0.0378 (2) | 0.89986 (9) | 0.15664 (8) | 0.0174 (4) | |
| C56 | −0.2033 (2) | 0.80012 (9) | 0.13198 (8) | 0.0178 (4) | |
| C57 | −0.1327 (2) | 0.84514 (9) | 0.06163 (7) | 0.0166 (4) | |
| C58 | 0.1483 (3) | 1.01300 (9) | 0.19478 (8) | 0.0248 (4) | |
| C59 | 0.2904 (2) | 0.99697 (10) | 0.15752 (9) | 0.0272 (4) | |
| H59A | 0.3469 | 1.0408 | 0.1554 | 0.033* | |
| H59B | 0.2346 | 0.9726 | 0.1174 | 0.033* | |
| C60 | 0.4322 (3) | 0.95702 (12) | 0.17192 (10) | 0.0369 (5) | |
| C61 | 0.2131 (3) | 1.05436 (12) | 0.25774 (10) | 0.0443 (6) | |
| H61A | 0.1186 | 1.0697 | 0.2772 | 0.067* | |
| H61B | 0.2928 | 1.0935 | 0.2578 | 0.067* | |
| H61C | 0.2696 | 1.0264 | 0.2786 | 0.067* | |
| C62 | 0.0340 (3) | 1.05308 (10) | 0.16575 (10) | 0.0329 (5) | |
| H62A | −0.0097 | 1.0266 | 0.1255 | 0.049* | |
| H62B | 0.0990 | 1.0957 | 0.1656 | 0.049* | |
| H62C | −0.0598 | 1.0624 | 0.1877 | 0.049* | |
| C63 | 0.3762 (5) | 0.8940 (2) | 0.1873 (2) | 0.0516 (10) | 0.753 (4) |
| H63A | 0.2909 | 0.8649 | 0.1559 | 0.077* | 0.753 (4) |
| H63B | 0.3283 | 0.9053 | 0.2238 | 0.077* | 0.753 (4) |
| H63C | 0.4725 | 0.8704 | 0.1922 | 0.077* | 0.753 (4) |
| C64 | 0.5174 (5) | 0.9369 (2) | 0.11552 (16) | 0.0456 (9) | 0.753 (4) |
| H64A | 0.6142 | 0.9146 | 0.1234 | 0.068* | 0.753 (4) |
| H64B | 0.5550 | 0.9774 | 0.1042 | 0.068* | 0.753 (4) |
| H64C | 0.4363 | 0.9060 | 0.0837 | 0.068* | 0.753 (4) |
| C65 | 0.5730 (5) | 1.0033 (2) | 0.21834 (18) | 0.0660 (12) | 0.753 (4) |
| H65A | 0.5355 | 1.0126 | 0.2568 | 0.099* | 0.753 (4) |
| H65B | 0.5999 | 1.0457 | 0.2086 | 0.099* | 0.753 (4) |
| H65C | 0.6733 | 0.9810 | 0.2192 | 0.099* | 0.753 (4) |
| C63' | 0.3532 (14) | 0.8805 (4) | 0.1520 (6) | 0.0510 (15) | 0.247 (4) |
| H63D | 0.4395 | 0.8530 | 0.1592 | 0.076* | 0.247 (4) |
| H63E | 0.3095 | 0.8672 | 0.1101 | 0.076* | 0.247 (4) |
| H63F | 0.2614 | 0.8734 | 0.1741 | 0.076* | 0.247 (4) |
| C64' | 0.5729 (13) | 0.9674 (6) | 0.1397 (5) | 0.0512 (14) | 0.247 (4) |
| H64D | 0.6533 | 0.9368 | 0.1446 | 0.077* | 0.247 (4) |
| H64E | 0.6291 | 1.0141 | 0.1550 | 0.077* | 0.247 (4) |
| H64F | 0.5301 | 0.9583 | 0.0981 | 0.077* | 0.247 (4) |
| C65' | 0.4932 (16) | 0.9692 (7) | 0.2389 (3) | 0.0663 (16) | 0.247 (4) |
| H65D | 0.4008 | 0.9531 | 0.2572 | 0.099* | 0.247 (4) |
| H65E | 0.5294 | 1.0174 | 0.2574 | 0.099* | 0.247 (4) |
| H65F | 0.5876 | 0.9446 | 0.2438 | 0.099* | 0.247 (4) |
| C66 | −0.0526 (2) | 0.89078 (9) | −0.01753 (8) | 0.0189 (4) | |
| H66A | −0.0379 | 0.9352 | 0.0120 | 0.023* | |
| H66B | −0.1213 | 0.8942 | −0.0531 | 0.023* | |
| C67 | 0.1189 (2) | 0.87506 (9) | −0.03230 (8) | 0.0195 (4) | |
| C68 | 0.1535 (3) | 0.80974 (10) | −0.04905 (10) | 0.0302 (5) | |
| H68 | 0.0697 | 0.7734 | −0.0504 | 0.036* | |
| C69 | 0.3099 (3) | 0.79679 (11) | −0.06397 (11) | 0.0372 (5) | |
| H69 | 0.3322 | 0.7517 | −0.0753 | 0.045* | |
| C70 | 0.4326 (3) | 0.84886 (11) | −0.06239 (9) | 0.0323 (5) | |
| H70 | 0.5399 | 0.8399 | −0.0721 | 0.039* | |
| C71 | 0.3991 (3) | 0.91358 (12) | −0.04675 (11) | 0.0394 (6) | |
| H71 | 0.4826 | 0.9497 | −0.0464 | 0.047* | |
| C72 | 0.2429 (3) | 0.92689 (11) | −0.03128 (11) | 0.0337 (5) | |
| H72 | 0.2214 | 0.9721 | −0.0199 | 0.040* | |
| H4 | 0.605 (3) | 0.4400 (10) | 0.2346 (10) | 0.024 (6)* | |
| H5 | 0.339 (3) | 0.3010 (12) | −0.0155 (10) | 0.035 (7)* | |
| H9 | 0.611 (3) | 0.3310 (10) | 0.2585 (9) | 0.021 (5)* | |
| H10 | 0.534 (3) | 0.4500 (12) | 0.5119 (10) | 0.037 (6)* | |
| H14 | 0.963 (3) | 0.1670 (10) | 0.7469 (9) | 0.022 (6)* | |
| H15 | 0.931 (3) | 0.0484 (12) | 0.4890 (11) | 0.039 (7)* | |
| H19 | 0.033 (3) | 0.9481 (12) | 0.2344 (11) | 0.034 (7)* | |
| H20 | −0.198 (3) | 0.8040 (12) | −0.0189 (10) | 0.030 (6)* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.0266 (2) | 0.0209 (2) | 0.0187 (2) | −0.00383 (18) | 0.00524 (17) | 0.00532 (17) |
| N1 | 0.0178 (7) | 0.0168 (7) | 0.0149 (7) | 0.0020 (6) | 0.0026 (6) | 0.0031 (6) |
| N2 | 0.0189 (8) | 0.0175 (7) | 0.0151 (7) | −0.0007 (6) | 0.0026 (6) | 0.0031 (6) |
| N3 | 0.0168 (7) | 0.0171 (7) | 0.0147 (7) | 0.0007 (6) | 0.0035 (6) | 0.0030 (6) |
| N4 | 0.0217 (8) | 0.0162 (7) | 0.0142 (7) | −0.0009 (6) | 0.0035 (6) | 0.0023 (6) |
| N5 | 0.0199 (8) | 0.0183 (8) | 0.0157 (7) | −0.0026 (6) | 0.0006 (6) | 0.0038 (6) |
| C1 | 0.0158 (8) | 0.0160 (8) | 0.0157 (8) | 0.0026 (7) | 0.0020 (7) | 0.0029 (7) |
| C2 | 0.0157 (8) | 0.0170 (8) | 0.0173 (8) | 0.0033 (7) | 0.0057 (7) | 0.0038 (7) |
| C3 | 0.0141 (8) | 0.0166 (8) | 0.0167 (8) | 0.0023 (7) | 0.0023 (7) | 0.0036 (7) |
| C4 | 0.0206 (9) | 0.0130 (8) | 0.0205 (9) | −0.0016 (7) | 0.0028 (7) | 0.0018 (7) |
| C5 | 0.0203 (9) | 0.0194 (9) | 0.0217 (9) | 0.0012 (7) | 0.0035 (7) | 0.0057 (7) |
| C6 | 0.0182 (9) | 0.0296 (10) | 0.0231 (10) | 0.0044 (8) | 0.0020 (7) | 0.0063 (8) |
| C7 | 0.0290 (11) | 0.0214 (10) | 0.0228 (10) | −0.0039 (8) | 0.0045 (8) | −0.0019 (8) |
| C8 | 0.0290 (11) | 0.0205 (10) | 0.0312 (11) | 0.0065 (8) | 0.0068 (8) | 0.0069 (8) |
| C9 | 0.068 (8) | 0.051 (6) | 0.038 (5) | 0.035 (5) | −0.021 (5) | −0.004 (4) |
| C10 | 0.024 (3) | 0.033 (4) | 0.085 (8) | 0.015 (3) | 0.014 (5) | 0.029 (5) |
| C11 | 0.035 (6) | 0.052 (8) | 0.048 (5) | 0.022 (5) | 0.018 (5) | 0.014 (5) |
| C9' | 0.020 (3) | 0.093 (7) | 0.060 (5) | 0.020 (4) | −0.012 (3) | −0.011 (4) |
| C10' | 0.044 (4) | 0.061 (4) | 0.064 (5) | 0.032 (3) | 0.021 (4) | 0.041 (4) |
| C11' | 0.031 (4) | 0.048 (5) | 0.039 (3) | 0.020 (3) | 0.017 (3) | 0.019 (3) |
| C12 | 0.0228 (9) | 0.0192 (9) | 0.0168 (8) | −0.0002 (7) | 0.0016 (7) | 0.0058 (7) |
| C13 | 0.0226 (9) | 0.0224 (9) | 0.0144 (8) | 0.0018 (7) | 0.0020 (7) | 0.0053 (7) |
| C14 | 0.0273 (11) | 0.0243 (10) | 0.0393 (12) | 0.0045 (8) | 0.0091 (9) | 0.0075 (9) |
| C15 | 0.0358 (13) | 0.0325 (12) | 0.0438 (13) | 0.0132 (10) | 0.0122 (10) | 0.0091 (10) |
| C16 | 0.0247 (11) | 0.0465 (13) | 0.0271 (11) | 0.0078 (10) | 0.0068 (8) | 0.0086 (10) |
| C17 | 0.0268 (11) | 0.0407 (13) | 0.0398 (13) | −0.0001 (10) | 0.0099 (9) | 0.0162 (10) |
| C18 | 0.0295 (11) | 0.0264 (11) | 0.0370 (12) | 0.0028 (9) | 0.0081 (9) | 0.0137 (9) |
| Cl2 | 0.0296 (2) | 0.0206 (2) | 0.0194 (2) | 0.00947 (18) | 0.00033 (18) | 0.00568 (17) |
| N6 | 0.0208 (8) | 0.0187 (8) | 0.0141 (7) | 0.0046 (6) | 0.0032 (6) | 0.0033 (6) |
| N7 | 0.0218 (8) | 0.0183 (8) | 0.0146 (7) | 0.0033 (6) | 0.0019 (6) | 0.0037 (6) |
| N8 | 0.0196 (8) | 0.0182 (7) | 0.0151 (7) | 0.0050 (6) | 0.0014 (6) | 0.0033 (6) |
| N9 | 0.0264 (8) | 0.0175 (8) | 0.0145 (7) | 0.0064 (6) | 0.0025 (6) | 0.0040 (6) |
| N10 | 0.0252 (8) | 0.0208 (8) | 0.0149 (7) | 0.0081 (7) | 0.0047 (6) | 0.0058 (6) |
| C19 | 0.0170 (8) | 0.0168 (8) | 0.0149 (8) | 0.0013 (7) | 0.0012 (7) | 0.0029 (7) |
| C20 | 0.0165 (8) | 0.0156 (8) | 0.0183 (8) | 0.0020 (7) | −0.0003 (7) | 0.0040 (7) |
| C21 | 0.0163 (8) | 0.0170 (8) | 0.0149 (8) | 0.0004 (7) | 0.0004 (7) | 0.0037 (7) |
| C22 | 0.0235 (9) | 0.0169 (9) | 0.0183 (9) | 0.0051 (7) | 0.0024 (7) | 0.0033 (7) |
| C23 | 0.0235 (10) | 0.0241 (10) | 0.0191 (9) | 0.0071 (8) | 0.0042 (7) | 0.0065 (8) |
| C24 | 0.0192 (10) | 0.0355 (11) | 0.0263 (10) | 0.0056 (8) | 0.0042 (8) | 0.0051 (9) |
| C25 | 0.0372 (12) | 0.0232 (10) | 0.0199 (9) | 0.0111 (9) | 0.0027 (8) | −0.0002 (8) |
| C26 | 0.0255 (10) | 0.0202 (10) | 0.0308 (11) | 0.0007 (8) | 0.0018 (8) | 0.0059 (8) |
| C27 | 0.0255 (12) | 0.090 (2) | 0.0485 (16) | −0.0002 (13) | −0.0087 (11) | 0.0279 (15) |
| C28 | 0.0269 (12) | 0.0358 (14) | 0.086 (2) | −0.0069 (10) | 0.0103 (13) | 0.0010 (13) |
| C29 | 0.0297 (13) | 0.0741 (19) | 0.0410 (14) | −0.0010 (12) | 0.0176 (11) | 0.0059 (13) |
| C30 | 0.0246 (10) | 0.0178 (9) | 0.0163 (8) | 0.0038 (7) | 0.0031 (7) | 0.0048 (7) |
| C31 | 0.0230 (10) | 0.0217 (9) | 0.0164 (8) | 0.0053 (7) | 0.0026 (7) | 0.0043 (7) |
| C32 | 0.0278 (11) | 0.0295 (11) | 0.0550 (15) | 0.0055 (9) | 0.0019 (10) | 0.0213 (11) |
| C33 | 0.0304 (12) | 0.0454 (14) | 0.0543 (15) | 0.0130 (11) | 0.0030 (11) | 0.0278 (12) |
| C34 | 0.0259 (12) | 0.0445 (14) | 0.0484 (15) | 0.0061 (10) | −0.0071 (10) | 0.0026 (11) |
| C35 | 0.0333 (15) | 0.0303 (14) | 0.128 (3) | −0.0046 (11) | −0.0209 (17) | 0.0017 (16) |
| C36 | 0.0322 (13) | 0.0213 (11) | 0.096 (2) | 0.0017 (10) | −0.0116 (13) | 0.0069 (13) |
| Cl3 | 0.0402 (3) | 0.0260 (2) | 0.0201 (2) | 0.0180 (2) | −0.0017 (2) | 0.00425 (18) |
| N11 | 0.0196 (8) | 0.0164 (7) | 0.0154 (7) | 0.0038 (6) | 0.0024 (6) | 0.0015 (6) |
| N12 | 0.0221 (8) | 0.0192 (8) | 0.0164 (7) | 0.0048 (6) | 0.0007 (6) | 0.0028 (6) |
| N13 | 0.0211 (8) | 0.0186 (8) | 0.0160 (7) | 0.0055 (6) | 0.0007 (6) | 0.0028 (6) |
| N14 | 0.0267 (9) | 0.0209 (8) | 0.0145 (8) | 0.0077 (7) | −0.0003 (6) | 0.0028 (6) |
| N15 | 0.0250 (8) | 0.0177 (8) | 0.0139 (7) | 0.0077 (6) | 0.0019 (6) | 0.0037 (6) |
| C37 | 0.0166 (8) | 0.0185 (9) | 0.0158 (8) | 0.0019 (7) | 0.0005 (7) | 0.0028 (7) |
| C38 | 0.0202 (9) | 0.0181 (9) | 0.0176 (9) | 0.0035 (7) | −0.0004 (7) | 0.0034 (7) |
| C39 | 0.0165 (8) | 0.0172 (9) | 0.0152 (8) | 0.0011 (7) | 0.0016 (7) | 0.0029 (7) |
| C40 | 0.0268 (10) | 0.0176 (9) | 0.0172 (9) | 0.0066 (8) | 0.0034 (7) | 0.0010 (7) |
| C41 | 0.0227 (9) | 0.0184 (9) | 0.0223 (9) | 0.0045 (7) | 0.0078 (7) | 0.0060 (7) |
| C42 | 0.0226 (10) | 0.0205 (9) | 0.0268 (10) | 0.0056 (8) | 0.0089 (8) | 0.0066 (8) |
| C43 | 0.0238 (10) | 0.0200 (9) | 0.0299 (10) | 0.0022 (8) | 0.0041 (8) | 0.0048 (8) |
| C44 | 0.0431 (13) | 0.0254 (11) | 0.0196 (10) | 0.0114 (9) | 0.0026 (9) | −0.0003 (8) |
| C45 | 0.0362 (12) | 0.0264 (11) | 0.0367 (12) | 0.0141 (9) | 0.0147 (10) | 0.0077 (9) |
| C46 | 0.0236 (11) | 0.0337 (12) | 0.0494 (14) | 0.0061 (9) | 0.0093 (10) | 0.0121 (10) |
| C47 | 0.0295 (11) | 0.0308 (11) | 0.0298 (11) | 0.0086 (9) | 0.0038 (9) | 0.0116 (9) |
| C48 | 0.0232 (9) | 0.0180 (9) | 0.0179 (9) | 0.0061 (7) | 0.0022 (7) | 0.0067 (7) |
| C49 | 0.0229 (9) | 0.0165 (9) | 0.0194 (9) | 0.0058 (7) | 0.0032 (7) | 0.0025 (7) |
| C50 | 0.0270 (10) | 0.0220 (10) | 0.0254 (10) | 0.0038 (8) | 0.0037 (8) | 0.0079 (8) |
| C51 | 0.0251 (10) | 0.0256 (11) | 0.0399 (12) | 0.0004 (8) | 0.0076 (9) | 0.0118 (9) |
| C52 | 0.0215 (11) | 0.0406 (13) | 0.0487 (14) | 0.0049 (9) | 0.0002 (10) | 0.0189 (11) |
| C53 | 0.0264 (12) | 0.0508 (15) | 0.0516 (15) | 0.0071 (10) | −0.0016 (10) | 0.0319 (12) |
| C54 | 0.0254 (11) | 0.0365 (12) | 0.0333 (11) | 0.0069 (9) | 0.0040 (9) | 0.0193 (9) |
| Cl4 | 0.0315 (3) | 0.0222 (2) | 0.0201 (2) | −0.00605 (19) | 0.00489 (19) | 0.00582 (18) |
| N16 | 0.0177 (7) | 0.0193 (8) | 0.0150 (7) | 0.0001 (6) | 0.0011 (6) | 0.0041 (6) |
| N17 | 0.0204 (8) | 0.0188 (8) | 0.0152 (7) | −0.0013 (6) | 0.0006 (6) | 0.0035 (6) |
| N18 | 0.0185 (8) | 0.0182 (7) | 0.0143 (7) | −0.0005 (6) | 0.0025 (6) | 0.0036 (6) |
| N19 | 0.0239 (8) | 0.0191 (8) | 0.0154 (8) | −0.0040 (6) | 0.0014 (6) | 0.0022 (6) |
| N20 | 0.0215 (8) | 0.0185 (8) | 0.0129 (7) | −0.0019 (6) | 0.0012 (6) | 0.0023 (6) |
| C55 | 0.0157 (8) | 0.0188 (9) | 0.0163 (8) | 0.0020 (7) | 0.0016 (7) | 0.0031 (7) |
| C56 | 0.0194 (9) | 0.0163 (8) | 0.0178 (8) | 0.0011 (7) | 0.0039 (7) | 0.0050 (7) |
| C57 | 0.0144 (8) | 0.0180 (9) | 0.0172 (8) | 0.0036 (7) | 0.0029 (7) | 0.0040 (7) |
| C58 | 0.0279 (10) | 0.0185 (9) | 0.0228 (10) | −0.0068 (8) | 0.0027 (8) | 0.0017 (8) |
| C59 | 0.0216 (10) | 0.0275 (10) | 0.0321 (11) | −0.0030 (8) | 0.0028 (8) | 0.0109 (9) |
| C60 | 0.0231 (11) | 0.0446 (14) | 0.0434 (13) | 0.0027 (10) | 0.0001 (9) | 0.0160 (11) |
| C61 | 0.0544 (16) | 0.0348 (13) | 0.0290 (12) | −0.0208 (11) | 0.0066 (11) | −0.0054 (10) |
| C62 | 0.0352 (12) | 0.0207 (10) | 0.0449 (13) | 0.0040 (9) | 0.0109 (10) | 0.0110 (9) |
| C63 | 0.0415 (17) | 0.059 (2) | 0.072 (2) | 0.0204 (15) | 0.0201 (19) | 0.039 (2) |
| C64 | 0.0376 (18) | 0.056 (2) | 0.0485 (19) | 0.0175 (15) | 0.0118 (15) | 0.0174 (16) |
| C65 | 0.0374 (19) | 0.084 (3) | 0.063 (2) | 0.0076 (17) | −0.0108 (16) | 0.0044 (19) |
| C63' | 0.041 (2) | 0.057 (2) | 0.070 (3) | 0.019 (2) | 0.019 (3) | 0.034 (3) |
| C64' | 0.043 (2) | 0.058 (3) | 0.056 (3) | 0.015 (2) | 0.011 (2) | 0.016 (2) |
| C65' | 0.044 (2) | 0.080 (3) | 0.063 (3) | 0.009 (2) | −0.013 (2) | 0.009 (2) |
| C66 | 0.0221 (9) | 0.0189 (9) | 0.0171 (8) | 0.0026 (7) | 0.0037 (7) | 0.0073 (7) |
| C67 | 0.0202 (9) | 0.0220 (9) | 0.0162 (8) | 0.0039 (7) | 0.0020 (7) | 0.0054 (7) |
| C68 | 0.0258 (11) | 0.0222 (10) | 0.0408 (12) | 0.0018 (8) | 0.0078 (9) | 0.0052 (9) |
| C69 | 0.0312 (12) | 0.0275 (11) | 0.0503 (14) | 0.0106 (9) | 0.0112 (10) | 0.0016 (10) |
| C70 | 0.0243 (11) | 0.0393 (12) | 0.0343 (12) | 0.0103 (9) | 0.0079 (9) | 0.0082 (10) |
| C71 | 0.0256 (11) | 0.0326 (12) | 0.0641 (16) | 0.0034 (9) | 0.0151 (11) | 0.0175 (11) |
| C72 | 0.0263 (11) | 0.0217 (10) | 0.0554 (14) | 0.0052 (8) | 0.0117 (10) | 0.0120 (10) |
| Cl1—C2 | 1.7489 (19) | Cl3—C38 | 1.7472 (19) |
| N1—C3 | 1.342 (2) | N11—C37 | 1.340 (2) |
| N1—C1 | 1.342 (2) | N11—C39 | 1.342 (2) |
| N2—C2 | 1.313 (2) | N12—C38 | 1.314 (2) |
| N2—C1 | 1.372 (2) | N12—C37 | 1.380 (2) |
| N3—C2 | 1.319 (2) | N13—C38 | 1.319 (2) |
| N3—C3 | 1.370 (2) | N13—C39 | 1.367 (2) |
| N4—C1 | 1.336 (2) | N14—C37 | 1.334 (2) |
| N4—C4 | 1.480 (2) | N14—C40 | 1.490 (2) |
| N4—H4 | 0.85 (2) | N14—H14 | 0.84 (2) |
| N5—C3 | 1.336 (2) | N15—C39 | 1.336 (2) |
| N5—C12 | 1.454 (2) | N15—C48 | 1.453 (2) |
| N5—H5 | 0.85 (2) | N15—H15 | 0.89 (2) |
| C4—C7 | 1.532 (3) | C40—C43 | 1.521 (3) |
| C4—C8 | 1.542 (3) | C40—C44 | 1.534 (3) |
| C4—C5 | 1.546 (3) | C40—C41 | 1.558 (3) |
| C5—C6 | 1.552 (3) | C41—C42 | 1.553 (3) |
| C5—H5A | 0.9900 | C41—H41A | 0.9900 |
| C5—H5B | 0.9900 | C41—H41B | 0.9900 |
| C6—C10' | 1.522 (6) | C42—C45 | 1.531 (3) |
| C6—C11' | 1.530 (6) | C42—C47 | 1.531 (3) |
| C6—C11 | 1.533 (8) | C42—C46 | 1.542 (3) |
| C6—C9 | 1.535 (7) | C43—H43A | 0.9800 |
| C6—C9' | 1.536 (6) | C43—H43B | 0.9800 |
| C6—C10 | 1.540 (7) | C43—H43C | 0.9800 |
| C7—H7A | 0.9800 | C44—H44A | 0.9800 |
| C7—H7B | 0.9800 | C44—H44B | 0.9800 |
| C7—H7C | 0.9800 | C44—H44C | 0.9800 |
| C8—H8A | 0.9800 | C45—H45A | 0.9800 |
| C8—H8B | 0.9800 | C45—H45B | 0.9800 |
| C8—H8C | 0.9800 | C45—H45C | 0.9800 |
| C9—H9A | 0.9800 | C46—H46A | 0.9800 |
| C9—H9B | 0.9800 | C46—H46B | 0.9800 |
| C9—H9C | 0.9800 | C46—H46C | 0.9800 |
| C10—H10A | 0.9800 | C47—H47A | 0.9800 |
| C10—H10B | 0.9800 | C47—H47B | 0.9800 |
| C10—H10C | 0.9800 | C47—H47C | 0.9800 |
| C11—H11A | 0.9800 | C48—C49 | 1.522 (3) |
| C11—H11B | 0.9800 | C48—H48A | 0.9900 |
| C11—H11C | 0.9800 | C48—H48B | 0.9900 |
| C9'—H9'1 | 0.9800 | C49—C50 | 1.385 (3) |
| C9'—H9'2 | 0.9800 | C49—C54 | 1.392 (3) |
| C9'—H9'3 | 0.9800 | C50—C51 | 1.392 (3) |
| C10'—H10D | 0.9800 | C50—H50 | 0.9500 |
| C10'—H10E | 0.9800 | C51—C52 | 1.384 (3) |
| C10'—H10F | 0.9800 | C51—H51 | 0.9500 |
| C11'—H11D | 0.9800 | C52—C53 | 1.376 (3) |
| C11'—H11E | 0.9800 | C52—H52 | 0.9500 |
| C11'—H11F | 0.9800 | C53—C54 | 1.390 (3) |
| C12—C13 | 1.517 (3) | C53—H53 | 0.9500 |
| C12—H12A | 0.9900 | C54—H54 | 0.9500 |
| C12—H12B | 0.9900 | Cl4—C56 | 1.7480 (19) |
| C13—C14 | 1.384 (3) | N16—C55 | 1.340 (2) |
| C13—C18 | 1.393 (3) | N16—C57 | 1.342 (2) |
| C14—C15 | 1.395 (3) | N17—C56 | 1.311 (2) |
| C14—H14A | 0.9500 | N17—C55 | 1.376 (2) |
| C15—C16 | 1.381 (3) | N18—C56 | 1.317 (2) |
| C15—H15A | 0.9500 | N18—C57 | 1.370 (2) |
| C16—C17 | 1.376 (3) | N19—C55 | 1.332 (2) |
| C16—H16 | 0.9500 | N19—C58 | 1.483 (2) |
| C17—C18 | 1.394 (3) | N19—H19 | 0.87 (2) |
| C17—H17 | 0.9500 | N20—C57 | 1.336 (2) |
| C18—H18 | 0.9500 | N20—C66 | 1.451 (2) |
| Cl2—C20 | 1.7475 (18) | N20—H20 | 0.87 (2) |
| N6—C19 | 1.340 (2) | C58—C61 | 1.527 (3) |
| N6—C21 | 1.344 (2) | C58—C62 | 1.541 (3) |
| N7—C20 | 1.315 (2) | C58—C59 | 1.546 (3) |
| N7—C19 | 1.374 (2) | C59—C60 | 1.552 (3) |
| N8—C20 | 1.319 (2) | C59—H59A | 0.9900 |
| N8—C21 | 1.365 (2) | C59—H59B | 0.9900 |
| N9—C19 | 1.340 (2) | C60—C64' | 1.473 (7) |
| N9—C22 | 1.485 (2) | C60—C63 | 1.490 (4) |
| N9—H9 | 0.87 (2) | C60—C65 | 1.540 (4) |
| N10—C21 | 1.336 (2) | C60—C64 | 1.566 (4) |
| N10—C30 | 1.448 (2) | C60—C65' | 1.572 (7) |
| N10—H10 | 0.93 (2) | C60—C63' | 1.574 (8) |
| C22—C25 | 1.534 (3) | C61—H61A | 0.9800 |
| C22—C26 | 1.537 (3) | C61—H61B | 0.9800 |
| C22—C23 | 1.553 (3) | C61—H61C | 0.9800 |
| C23—C24 | 1.545 (3) | C62—H62A | 0.9800 |
| C23—H23A | 0.9900 | C62—H62B | 0.9800 |
| C23—H23B | 0.9900 | C62—H62C | 0.9800 |
| C24—C28 | 1.523 (3) | C63—H63A | 0.9800 |
| C24—C29 | 1.532 (3) | C63—H63B | 0.9800 |
| C24—C27 | 1.535 (3) | C63—H63C | 0.9800 |
| C25—H25A | 0.9800 | C64—H64A | 0.9800 |
| C25—H25B | 0.9800 | C64—H64B | 0.9800 |
| C25—H25C | 0.9800 | C64—H64C | 0.9800 |
| C26—H26A | 0.9800 | C65—H65A | 0.9800 |
| C26—H26B | 0.9800 | C65—H65B | 0.9800 |
| C26—H26C | 0.9800 | C65—H65C | 0.9800 |
| C27—H27A | 0.9800 | C63'—H63D | 0.9800 |
| C27—H27B | 0.9800 | C63'—H63E | 0.9800 |
| C27—H27C | 0.9800 | C63'—H63F | 0.9800 |
| C28—H28A | 0.9800 | C64'—H64D | 0.9800 |
| C28—H28B | 0.9800 | C64'—H64E | 0.9800 |
| C28—H28C | 0.9800 | C64'—H64F | 0.9800 |
| C29—H29A | 0.9800 | C65'—H65D | 0.9800 |
| C29—H29B | 0.9800 | C65'—H65E | 0.9800 |
| C29—H29C | 0.9800 | C65'—H65F | 0.9800 |
| C30—C31 | 1.518 (3) | C66—C67 | 1.520 (3) |
| C30—H30A | 0.9900 | C66—H66A | 0.9900 |
| C30—H30B | 0.9900 | C66—H66B | 0.9900 |
| C31—C36 | 1.370 (3) | C67—C68 | 1.382 (3) |
| C31—C32 | 1.378 (3) | C67—C72 | 1.382 (3) |
| C32—C33 | 1.389 (3) | C68—C69 | 1.389 (3) |
| C32—H32 | 0.9500 | C68—H68 | 0.9500 |
| C33—C34 | 1.367 (3) | C69—C70 | 1.375 (3) |
| C33—H33 | 0.9500 | C69—H69 | 0.9500 |
| C34—C35 | 1.373 (4) | C70—C71 | 1.366 (3) |
| C34—H34 | 0.9500 | C70—H70 | 0.9500 |
| C35—C36 | 1.390 (3) | C71—C72 | 1.394 (3) |
| C35—H35 | 0.9500 | C71—H71 | 0.9500 |
| C36—H36 | 0.9500 | C72—H72 | 0.9500 |
| C3—N1—C1 | 114.95 (15) | C37—N11—C39 | 115.23 (15) |
| C2—N2—C1 | 112.59 (15) | C38—N12—C37 | 112.49 (15) |
| C2—N3—C3 | 112.39 (15) | C38—N13—C39 | 112.45 (15) |
| C1—N4—C4 | 128.27 (16) | C37—N14—C40 | 127.89 (16) |
| C1—N4—H4 | 112.2 (15) | C37—N14—H14 | 112.3 (14) |
| C4—N4—H4 | 119.4 (14) | C40—N14—H14 | 119.7 (14) |
| C3—N5—C12 | 122.93 (15) | C39—N15—C48 | 123.26 (15) |
| C3—N5—H5 | 115.9 (16) | C39—N15—H15 | 116.7 (15) |
| C12—N5—H5 | 120.8 (16) | C48—N15—H15 | 120.0 (15) |
| N4—C1—N1 | 120.58 (17) | N14—C37—N11 | 120.34 (16) |
| N4—C1—N2 | 114.53 (16) | N14—C37—N12 | 115.08 (16) |
| N1—C1—N2 | 124.89 (16) | N11—C37—N12 | 124.58 (16) |
| N2—C2—N3 | 129.94 (17) | N12—C38—N13 | 129.98 (17) |
| N2—C2—Cl1 | 115.24 (14) | N12—C38—Cl3 | 115.36 (14) |
| N3—C2—Cl1 | 114.81 (13) | N13—C38—Cl3 | 114.66 (13) |
| N5—C3—N1 | 118.79 (16) | N15—C39—N11 | 118.75 (16) |
| N5—C3—N3 | 116.04 (15) | N15—C39—N13 | 116.09 (15) |
| N1—C3—N3 | 125.16 (16) | N11—C39—N13 | 125.16 (16) |
| N4—C4—C7 | 104.89 (15) | N14—C40—C43 | 110.35 (16) |
| N4—C4—C8 | 109.24 (15) | N14—C40—C44 | 104.19 (15) |
| C7—C4—C8 | 108.56 (15) | C43—C40—C44 | 108.77 (16) |
| N4—C4—C5 | 113.26 (14) | N14—C40—C41 | 105.76 (15) |
| C7—C4—C5 | 113.24 (16) | C43—C40—C41 | 115.28 (16) |
| C8—C4—C5 | 107.53 (15) | C44—C40—C41 | 111.89 (16) |
| C4—C5—C6 | 123.98 (16) | C42—C41—C40 | 123.57 (16) |
| C4—C5—H5A | 106.3 | C42—C41—H41A | 106.4 |
| C6—C5—H5A | 106.3 | C40—C41—H41A | 106.4 |
| C4—C5—H5B | 106.3 | C42—C41—H41B | 106.4 |
| C6—C5—H5B | 106.3 | C40—C41—H41B | 106.4 |
| H5A—C5—H5B | 106.4 | H41A—C41—H41B | 106.5 |
| C10'—C6—C11' | 108.6 (4) | C45—C42—C47 | 109.11 (17) |
| C10'—C6—C11 | 123.2 (7) | C45—C42—C46 | 107.95 (17) |
| C11'—C6—C11 | 18.8 (5) | C47—C42—C46 | 107.61 (17) |
| C10'—C6—C9 | 87.4 (5) | C45—C42—C41 | 114.06 (17) |
| C11'—C6—C9 | 120.3 (8) | C47—C42—C41 | 112.53 (16) |
| C11—C6—C9 | 106.5 (7) | C46—C42—C41 | 105.22 (16) |
| C10'—C6—C9' | 109.5 (4) | C40—C43—H43A | 109.5 |
| C11'—C6—C9' | 107.6 (5) | C40—C43—H43B | 109.5 |
| C11—C6—C9' | 90.5 (7) | H43A—C43—H43B | 109.5 |
| C9—C6—C9' | 22.4 (6) | C40—C43—H43C | 109.5 |
| C10'—C6—C10 | 22.8 (4) | H43A—C43—H43C | 109.5 |
| C11'—C6—C10 | 89.9 (6) | H43B—C43—H43C | 109.5 |
| C11—C6—C10 | 107.2 (5) | C40—C44—H44A | 109.5 |
| C9—C6—C10 | 108.5 (5) | C40—C44—H44B | 109.5 |
| C9'—C6—C10 | 129.4 (5) | H44A—C44—H44B | 109.5 |
| C10'—C6—C5 | 114.8 (4) | C40—C44—H44C | 109.5 |
| C11'—C6—C5 | 106.8 (5) | H44A—C44—H44C | 109.5 |
| C11—C6—C5 | 106.5 (7) | H44B—C44—H44C | 109.5 |
| C9—C6—C5 | 117.6 (6) | C42—C45—H45A | 109.5 |
| C9'—C6—C5 | 109.3 (5) | C42—C45—H45B | 109.5 |
| C10—C6—C5 | 110.0 (4) | H45A—C45—H45B | 109.5 |
| C4—C7—H7A | 109.5 | C42—C45—H45C | 109.5 |
| C4—C7—H7B | 109.5 | H45A—C45—H45C | 109.5 |
| H7A—C7—H7B | 109.5 | H45B—C45—H45C | 109.5 |
| C4—C7—H7C | 109.5 | C42—C46—H46A | 109.5 |
| H7A—C7—H7C | 109.5 | C42—C46—H46B | 109.5 |
| H7B—C7—H7C | 109.5 | H46A—C46—H46B | 109.5 |
| C4—C8—H8A | 109.5 | C42—C46—H46C | 109.5 |
| C4—C8—H8B | 109.5 | H46A—C46—H46C | 109.5 |
| H8A—C8—H8B | 109.5 | H46B—C46—H46C | 109.5 |
| C4—C8—H8C | 109.5 | C42—C47—H47A | 109.5 |
| H8A—C8—H8C | 109.5 | C42—C47—H47B | 109.5 |
| H8B—C8—H8C | 109.5 | H47A—C47—H47B | 109.5 |
| C6—C9—H9A | 109.5 | C42—C47—H47C | 109.5 |
| C6—C9—H9B | 109.5 | H47A—C47—H47C | 109.5 |
| C6—C9—H9C | 109.5 | H47B—C47—H47C | 109.5 |
| C6—C10—H10A | 109.5 | N15—C48—C49 | 114.48 (16) |
| C6—C10—H10B | 109.5 | N15—C48—H48A | 108.6 |
| C6—C10—H10C | 109.5 | C49—C48—H48A | 108.6 |
| C6—C11—H11A | 109.5 | N15—C48—H48B | 108.6 |
| C6—C11—H11B | 109.5 | C49—C48—H48B | 108.6 |
| C6—C11—H11C | 109.5 | H48A—C48—H48B | 107.6 |
| C6—C9'—H9'1 | 109.5 | C50—C49—C54 | 118.62 (18) |
| C6—C9'—H9'2 | 109.5 | C50—C49—C48 | 122.09 (17) |
| H9'1—C9'—H9'2 | 109.5 | C54—C49—C48 | 119.22 (18) |
| C6—C9'—H9'3 | 109.5 | C49—C50—C51 | 120.71 (19) |
| H9'1—C9'—H9'3 | 109.5 | C49—C50—H50 | 119.6 |
| H9'2—C9'—H9'3 | 109.5 | C51—C50—H50 | 119.6 |
| C6—C10'—H10D | 109.5 | C52—C51—C50 | 120.0 (2) |
| C6—C10'—H10E | 109.5 | C52—C51—H51 | 120.0 |
| H10D—C10'—H10E | 109.5 | C50—C51—H51 | 120.0 |
| C6—C10'—H10F | 109.5 | C53—C52—C51 | 119.8 (2) |
| H10D—C10'—H10F | 109.5 | C53—C52—H52 | 120.1 |
| H10E—C10'—H10F | 109.5 | C51—C52—H52 | 120.1 |
| C6—C11'—H11D | 109.5 | C52—C53—C54 | 120.2 (2) |
| C6—C11'—H11E | 109.5 | C52—C53—H53 | 119.9 |
| H11D—C11'—H11E | 109.5 | C54—C53—H53 | 119.9 |
| C6—C11'—H11F | 109.5 | C53—C54—C49 | 120.7 (2) |
| H11D—C11'—H11F | 109.5 | C53—C54—H54 | 119.7 |
| H11E—C11'—H11F | 109.5 | C49—C54—H54 | 119.7 |
| N5—C12—C13 | 114.27 (15) | C55—N16—C57 | 115.08 (16) |
| N5—C12—H12A | 108.7 | C56—N17—C55 | 112.68 (15) |
| C13—C12—H12A | 108.7 | C56—N18—C57 | 112.29 (15) |
| N5—C12—H12B | 108.7 | C55—N19—C58 | 128.10 (17) |
| C13—C12—H12B | 108.7 | C55—N19—H19 | 113.4 (16) |
| H12A—C12—H12B | 107.6 | C58—N19—H19 | 118.4 (16) |
| C14—C13—C18 | 118.67 (18) | C57—N20—C66 | 123.28 (16) |
| C14—C13—C12 | 122.10 (18) | C57—N20—H20 | 115.8 (15) |
| C18—C13—C12 | 119.18 (17) | C66—N20—H20 | 120.4 (15) |
| C13—C14—C15 | 120.6 (2) | N19—C55—N16 | 121.02 (17) |
| C13—C14—H14A | 119.7 | N19—C55—N17 | 114.32 (16) |
| C15—C14—H14A | 119.7 | N16—C55—N17 | 124.66 (16) |
| C16—C15—C14 | 120.3 (2) | N17—C56—N18 | 130.00 (17) |
| C16—C15—H15A | 119.9 | N17—C56—Cl4 | 114.97 (14) |
| C14—C15—H15A | 119.9 | N18—C56—Cl4 | 115.02 (14) |
| C17—C16—C15 | 119.5 (2) | N20—C57—N16 | 118.83 (17) |
| C17—C16—H16 | 120.2 | N20—C57—N18 | 115.96 (16) |
| C15—C16—H16 | 120.2 | N16—C57—N18 | 125.21 (16) |
| C16—C17—C18 | 120.4 (2) | N19—C58—C61 | 105.07 (17) |
| C16—C17—H17 | 119.8 | N19—C58—C62 | 109.08 (16) |
| C18—C17—H17 | 119.8 | C61—C58—C62 | 108.82 (18) |
| C13—C18—C17 | 120.4 (2) | N19—C58—C59 | 112.79 (16) |
| C13—C18—H18 | 119.8 | C61—C58—C59 | 113.11 (18) |
| C17—C18—H18 | 119.8 | C62—C58—C59 | 107.85 (17) |
| C19—N6—C21 | 115.00 (15) | C58—C59—C60 | 124.08 (18) |
| C20—N7—C19 | 112.49 (15) | C58—C59—H59A | 106.3 |
| C20—N8—C21 | 112.58 (15) | C60—C59—H59A | 106.3 |
| C19—N9—C22 | 127.59 (16) | C58—C59—H59B | 106.3 |
| C19—N9—H9 | 113.5 (14) | C60—C59—H59B | 106.3 |
| C22—N9—H9 | 115.6 (14) | H59A—C59—H59B | 106.4 |
| C21—N10—C30 | 123.30 (15) | C64'—C60—C63 | 125.7 (5) |
| C21—N10—H10 | 116.1 (14) | C64'—C60—C65 | 75.0 (5) |
| C30—N10—H10 | 119.9 (14) | C63—C60—C65 | 111.7 (3) |
| N6—C19—N9 | 120.68 (16) | C64'—C60—C59 | 110.6 (5) |
| N6—C19—N7 | 124.97 (15) | C63—C60—C59 | 115.5 (2) |
| N9—C19—N7 | 114.34 (16) | C65—C60—C59 | 110.8 (2) |
| N7—C20—N8 | 129.78 (17) | C64'—C60—C64 | 30.0 (5) |
| N7—C20—Cl2 | 115.44 (14) | C63—C60—C64 | 107.6 (3) |
| N8—C20—Cl2 | 114.78 (13) | C65—C60—C64 | 104.2 (3) |
| N10—C21—N6 | 118.81 (16) | C59—C60—C64 | 106.2 (2) |
| N10—C21—N8 | 116.04 (15) | C64'—C60—C65' | 112.0 (6) |
| N6—C21—N8 | 125.14 (16) | C63—C60—C65' | 72.2 (5) |
| N9—C22—C25 | 105.41 (15) | C65—C60—C65' | 43.3 (5) |
| N9—C22—C26 | 108.75 (15) | C59—C60—C65' | 115.1 (5) |
| C25—C22—C26 | 107.91 (16) | C64—C60—C65' | 134.1 (5) |
| N9—C22—C23 | 113.99 (15) | C64'—C60—C63' | 109.6 (6) |
| C25—C22—C23 | 113.25 (16) | C63—C60—C63' | 30.6 (4) |
| C26—C22—C23 | 107.34 (16) | C65—C60—C63' | 137.7 (5) |
| C24—C23—C22 | 124.97 (17) | C59—C60—C63' | 106.5 (5) |
| C24—C23—H23A | 106.1 | C64—C60—C63' | 83.4 (5) |
| C22—C23—H23A | 106.1 | C65'—C60—C63' | 102.4 (6) |
| C24—C23—H23B | 106.1 | C58—C61—H61A | 109.5 |
| C22—C23—H23B | 106.1 | C58—C61—H61B | 109.5 |
| H23A—C23—H23B | 106.3 | H61A—C61—H61B | 109.5 |
| C28—C24—C29 | 109.1 (2) | C58—C61—H61C | 109.5 |
| C28—C24—C27 | 108.0 (2) | H61A—C61—H61C | 109.5 |
| C29—C24—C27 | 107.4 (2) | H61B—C61—H61C | 109.5 |
| C28—C24—C23 | 112.44 (17) | C58—C62—H62A | 109.5 |
| C29—C24—C23 | 114.03 (18) | C58—C62—H62B | 109.5 |
| C27—C24—C23 | 105.61 (18) | H62A—C62—H62B | 109.5 |
| C22—C25—H25A | 109.5 | C58—C62—H62C | 109.5 |
| C22—C25—H25B | 109.5 | H62A—C62—H62C | 109.5 |
| H25A—C25—H25B | 109.5 | H62B—C62—H62C | 109.5 |
| C22—C25—H25C | 109.5 | C60—C63—H63A | 109.5 |
| H25A—C25—H25C | 109.5 | C60—C63—H63B | 109.5 |
| H25B—C25—H25C | 109.5 | C60—C63—H63C | 109.5 |
| C22—C26—H26A | 109.5 | C60—C64—H64A | 109.5 |
| C22—C26—H26B | 109.5 | C60—C64—H64B | 109.5 |
| H26A—C26—H26B | 109.5 | C60—C64—H64C | 109.5 |
| C22—C26—H26C | 109.5 | C60—C65—H65A | 109.5 |
| H26A—C26—H26C | 109.5 | C60—C65—H65B | 109.5 |
| H26B—C26—H26C | 109.5 | C60—C65—H65C | 109.5 |
| C24—C27—H27A | 109.5 | C60—C63'—H63D | 109.5 |
| C24—C27—H27B | 109.5 | C60—C63'—H63E | 109.5 |
| H27A—C27—H27B | 109.5 | H63D—C63'—H63E | 109.5 |
| C24—C27—H27C | 109.5 | C60—C63'—H63F | 109.5 |
| H27A—C27—H27C | 109.5 | H63D—C63'—H63F | 109.5 |
| H27B—C27—H27C | 109.5 | H63E—C63'—H63F | 109.5 |
| C24—C28—H28A | 109.5 | C60—C64'—H64D | 109.5 |
| C24—C28—H28B | 109.5 | C60—C64'—H64E | 109.5 |
| H28A—C28—H28B | 109.5 | H64D—C64'—H64E | 109.5 |
| C24—C28—H28C | 109.5 | C60—C64'—H64F | 109.5 |
| H28A—C28—H28C | 109.5 | H64D—C64'—H64F | 109.5 |
| H28B—C28—H28C | 109.5 | H64E—C64'—H64F | 109.5 |
| C24—C29—H29A | 109.5 | C60—C65'—H65D | 109.5 |
| C24—C29—H29B | 109.5 | C60—C65'—H65E | 109.5 |
| H29A—C29—H29B | 109.5 | H65D—C65'—H65E | 109.5 |
| C24—C29—H29C | 109.5 | C60—C65'—H65F | 109.5 |
| H29A—C29—H29C | 109.5 | H65D—C65'—H65F | 109.5 |
| H29B—C29—H29C | 109.5 | H65E—C65'—H65F | 109.5 |
| N10—C30—C31 | 114.48 (16) | N20—C66—C67 | 114.16 (15) |
| N10—C30—H30A | 108.6 | N20—C66—H66A | 108.7 |
| C31—C30—H30A | 108.6 | C67—C66—H66A | 108.7 |
| N10—C30—H30B | 108.6 | N20—C66—H66B | 108.7 |
| C31—C30—H30B | 108.6 | C67—C66—H66B | 108.7 |
| H30A—C30—H30B | 107.6 | H66A—C66—H66B | 107.6 |
| C36—C31—C32 | 118.1 (2) | C68—C67—C72 | 118.38 (18) |
| C36—C31—C30 | 123.17 (18) | C68—C67—C66 | 121.88 (18) |
| C32—C31—C30 | 118.71 (18) | C72—C67—C66 | 119.70 (17) |
| C31—C32—C33 | 121.5 (2) | C67—C68—C69 | 120.6 (2) |
| C31—C32—H32 | 119.2 | C67—C68—H68 | 119.7 |
| C33—C32—H32 | 119.2 | C69—C68—H68 | 119.7 |
| C34—C33—C32 | 120.0 (2) | C70—C69—C68 | 120.4 (2) |
| C34—C33—H33 | 120.0 | C70—C69—H69 | 119.8 |
| C32—C33—H33 | 120.0 | C68—C69—H69 | 119.8 |
| C33—C34—C35 | 118.7 (2) | C71—C70—C69 | 119.5 (2) |
| C33—C34—H34 | 120.6 | C71—C70—H70 | 120.2 |
| C35—C34—H34 | 120.6 | C69—C70—H70 | 120.2 |
| C34—C35—C36 | 121.2 (2) | C70—C71—C72 | 120.2 (2) |
| C34—C35—H35 | 119.4 | C70—C71—H71 | 119.9 |
| C36—C35—H35 | 119.4 | C72—C71—H71 | 119.9 |
| C31—C36—C35 | 120.4 (2) | C67—C72—C71 | 120.8 (2) |
| C31—C36—H36 | 119.8 | C67—C72—H72 | 119.6 |
| C35—C36—H36 | 119.8 | C71—C72—H72 | 119.6 |
| C4—N4—C1—N1 | −1.5 (3) | C40—N14—C37—N11 | 5.8 (3) |
| C4—N4—C1—N2 | 177.59 (16) | C40—N14—C37—N12 | −173.85 (17) |
| C3—N1—C1—N4 | −178.05 (16) | C39—N11—C37—N14 | 177.08 (17) |
| C3—N1—C1—N2 | 3.0 (2) | C39—N11—C37—N12 | −3.3 (3) |
| C2—N2—C1—N4 | 177.79 (15) | C38—N12—C37—N14 | −176.42 (17) |
| C2—N2—C1—N1 | −3.2 (2) | C38—N12—C37—N11 | 3.9 (3) |
| C1—N2—C2—N3 | 1.1 (3) | C37—N12—C38—N13 | −1.5 (3) |
| C1—N2—C2—Cl1 | −178.40 (12) | C37—N12—C38—Cl3 | 178.67 (13) |
| C3—N3—C2—N2 | 0.9 (3) | C39—N13—C38—N12 | −1.2 (3) |
| C3—N3—C2—Cl1 | −179.60 (12) | C39—N13—C38—Cl3 | 178.60 (13) |
| C12—N5—C3—N1 | 3.7 (3) | C48—N15—C39—N11 | 4.8 (3) |
| C12—N5—C3—N3 | −177.45 (15) | C48—N15—C39—N13 | −174.53 (16) |
| C1—N1—C3—N5 | 178.20 (15) | C37—N11—C39—N15 | −179.27 (16) |
| C1—N1—C3—N3 | −0.6 (2) | C37—N11—C39—N13 | 0.1 (3) |
| C2—N3—C3—N5 | 180.00 (15) | C38—N13—C39—N15 | −178.64 (16) |
| C2—N3—C3—N1 | −1.2 (2) | C38—N13—C39—N11 | 2.0 (3) |
| C1—N4—C4—C7 | −179.82 (17) | C37—N14—C40—C43 | −61.0 (2) |
| C1—N4—C4—C8 | 64.0 (2) | C37—N14—C40—C44 | −177.59 (19) |
| C1—N4—C4—C5 | −55.9 (2) | C37—N14—C40—C41 | 64.3 (2) |
| N4—C4—C5—C6 | −58.9 (2) | N14—C40—C41—C42 | −169.69 (16) |
| C7—C4—C5—C6 | 60.4 (2) | C43—C40—C41—C42 | −47.5 (2) |
| C8—C4—C5—C6 | −179.71 (16) | C44—C40—C41—C42 | 77.5 (2) |
| C4—C5—C6—C10' | 45.1 (6) | C40—C41—C42—C45 | −50.4 (2) |
| C4—C5—C6—C11' | 165.5 (5) | C40—C41—C42—C47 | 74.6 (2) |
| C4—C5—C6—C11 | −174.9 (7) | C40—C41—C42—C46 | −168.54 (17) |
| C4—C5—C6—C9 | −55.6 (9) | C39—N15—C48—C49 | −98.3 (2) |
| C4—C5—C6—C9' | −78.3 (6) | N15—C48—C49—C50 | 36.4 (2) |
| C4—C5—C6—C10 | 69.3 (8) | N15—C48—C49—C54 | −146.64 (18) |
| C3—N5—C12—C13 | 86.8 (2) | C54—C49—C50—C51 | −0.8 (3) |
| N5—C12—C13—C14 | 20.3 (2) | C48—C49—C50—C51 | 176.20 (17) |
| N5—C12—C13—C18 | −162.29 (17) | C49—C50—C51—C52 | −0.1 (3) |
| C18—C13—C14—C15 | 0.8 (3) | C50—C51—C52—C53 | 0.9 (3) |
| C12—C13—C14—C15 | 178.20 (19) | C51—C52—C53—C54 | −0.7 (4) |
| C13—C14—C15—C16 | −0.3 (3) | C52—C53—C54—C49 | −0.2 (4) |
| C14—C15—C16—C17 | −0.3 (3) | C50—C49—C54—C53 | 0.9 (3) |
| C15—C16—C17—C18 | 0.4 (3) | C48—C49—C54—C53 | −176.1 (2) |
| C14—C13—C18—C17 | −0.7 (3) | C58—N19—C55—N16 | −1.9 (3) |
| C12—C13—C18—C17 | −178.15 (19) | C58—N19—C55—N17 | 177.43 (17) |
| C16—C17—C18—C13 | 0.0 (3) | C57—N16—C55—N19 | −178.45 (16) |
| C21—N6—C19—N9 | 179.58 (16) | C57—N16—C55—N17 | 2.2 (2) |
| C21—N6—C19—N7 | 0.8 (3) | C56—N17—C55—N19 | 177.13 (16) |
| C22—N9—C19—N6 | 7.0 (3) | C56—N17—C55—N16 | −3.5 (2) |
| C22—N9—C19—N7 | −174.08 (16) | C55—N17—C56—N18 | 2.7 (3) |
| C20—N7—C19—N6 | −2.1 (3) | C55—N17—C56—Cl4 | −178.07 (12) |
| C20—N7—C19—N9 | 179.06 (16) | C57—N18—C56—N17 | −0.6 (3) |
| C19—N7—C20—N8 | 2.3 (3) | C57—N18—C56—Cl4 | −179.83 (12) |
| C19—N7—C20—Cl2 | −177.57 (12) | C66—N20—C57—N16 | 3.8 (3) |
| C21—N8—C20—N7 | −1.1 (3) | C66—N20—C57—N18 | −177.05 (15) |
| C21—N8—C20—Cl2 | 178.76 (12) | C55—N16—C57—N20 | 179.26 (16) |
| C30—N10—C21—N6 | 3.2 (3) | C55—N16—C57—N18 | 0.2 (2) |
| C30—N10—C21—N8 | −177.96 (16) | C56—N18—C57—N20 | 179.90 (15) |
| C19—N6—C21—N10 | 179.27 (16) | C56—N18—C57—N16 | −1.0 (2) |
| C19—N6—C21—N8 | 0.6 (3) | C55—N19—C58—C61 | 179.9 (2) |
| C20—N8—C21—N10 | −179.21 (16) | C55—N19—C58—C62 | 63.4 (2) |
| C20—N8—C21—N6 | −0.5 (3) | C55—N19—C58—C59 | −56.4 (3) |
| C19—N9—C22—C25 | 175.88 (18) | N19—C58—C59—C60 | −59.4 (3) |
| C19—N9—C22—C26 | 60.4 (2) | C61—C58—C59—C60 | 59.7 (3) |
| C19—N9—C22—C23 | −59.3 (2) | C62—C58—C59—C60 | −179.89 (18) |
| N9—C22—C23—C24 | −56.2 (2) | C58—C59—C60—C64' | −163.0 (6) |
| C25—C22—C23—C24 | 64.3 (2) | C58—C59—C60—C63 | 46.5 (3) |
| C26—C22—C23—C24 | −176.73 (17) | C58—C59—C60—C65 | −81.8 (3) |
| C22—C23—C24—C28 | 66.9 (3) | C58—C59—C60—C64 | 165.7 (2) |
| C22—C23—C24—C29 | −58.0 (3) | C58—C59—C60—C65' | −34.8 (6) |
| C22—C23—C24—C27 | −175.60 (19) | C58—C59—C60—C63' | 77.9 (5) |
| C21—N10—C30—C31 | 87.3 (2) | C57—N20—C66—C67 | 90.7 (2) |
| N10—C30—C31—C36 | 16.8 (3) | N20—C66—C67—C68 | 28.2 (2) |
| N10—C30—C31—C32 | −165.53 (18) | N20—C66—C67—C72 | −154.30 (18) |
| C36—C31—C32—C33 | −0.3 (4) | C72—C67—C68—C69 | 0.6 (3) |
| C30—C31—C32—C33 | −178.0 (2) | C66—C67—C68—C69 | 178.1 (2) |
| C31—C32—C33—C34 | −0.6 (4) | C67—C68—C69—C70 | −0.1 (4) |
| C32—C33—C34—C35 | 1.0 (4) | C68—C69—C70—C71 | −0.8 (4) |
| C33—C34—C35—C36 | −0.4 (5) | C69—C70—C71—C72 | 1.4 (4) |
| C32—C31—C36—C35 | 0.8 (4) | C68—C67—C72—C71 | 0.0 (3) |
| C30—C31—C36—C35 | 178.5 (3) | C66—C67—C72—C71 | −177.6 (2) |
| C34—C35—C36—C31 | −0.5 (5) | C70—C71—C72—C67 | −0.9 (4) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N20—H20···N3i | 0.87 (2) | 2.14 (2) | 3.007 (2) | 179 (2) |
| N19—H19···N12ii | 0.87 (2) | 2.22 (2) | 3.085 (2) | 174 (2) |
| N15—H15···N13iii | 0.89 (2) | 2.06 (3) | 2.953 (2) | 176 (2) |
| N14—H14···N17ii | 0.84 (2) | 2.24 (2) | 3.078 (2) | 172 (2) |
| N10—H10···N8ii | 0.93 (2) | 2.06 (2) | 2.989 (2) | 171 (2) |
| N9—H9···N2 | 0.87 (2) | 2.29 (2) | 3.127 (2) | 163.3 (19) |
| N5—H5···N18i | 0.85 (2) | 2.14 (2) | 2.984 (2) | 172 (2) |
| N4—H4···N7 | 0.85 (2) | 2.24 (2) | 3.085 (2) | 174 (2) |
| Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+1, −z+1; (iii) −x+2, −y, −z+1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N20—H20···N3i | 0.87 (2) | 2.14 (2) | 3.007 (2) | 179 (2) |
| N19—H19···N12ii | 0.87 (2) | 2.22 (2) | 3.085 (2) | 174 (2) |
| N15—H15···N13iii | 0.89 (2) | 2.06 (3) | 2.953 (2) | 176 (2) |
| N14—H14···N17ii | 0.84 (2) | 2.24 (2) | 3.078 (2) | 172 (2) |
| N10—H10···N8ii | 0.93 (2) | 2.06 (2) | 2.989 (2) | 171 (2) |
| N9—H9···N2 | 0.87 (2) | 2.29 (2) | 3.127 (2) | 163.3 (19) |
| N5—H5···N18i | 0.85 (2) | 2.14 (2) | 2.984 (2) | 172 (2) |
| N4—H4···N7 | 0.85 (2) | 2.24 (2) | 3.085 (2) | 174 (2) |
| Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+1, −z+1; (iii) −x+2, −y, −z+1. |
Borzatta, V. & Carrozza, P. (1991). Eur. Patent EP 0 462 069.
Deng, Y., Wang, X.-J., Wen, F., Wang, L. & Zhang, Y. (2006). Acta Cryst. E62, o5207–o5208.
Kaiser, D. W. & Thurston, J. T. (1951). J. Am. Chem. Soc. 73, 2984–2986.
Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA .
Sheldrick, G. M. (1996). SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.
The title compound, (I), is an important intermediate in the preparation of hindered light stabilizers (Borzatta & Carrozza, 1991; Deng et al., 2006).
There are four molecules of (I) in the asymmetic unit, with simplar conformations, although two of the molecules show disorder of their tert-butyl groupings. In each case, the triazine ring is essentially planar (Fig. 1). The molecules are linked by strong, near-linear, intermolecular N—H···N hydrogen bonds (Table 1).