Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807042559/hb2528sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807042559/hb2528Isup2.hkl |
CCDC reference: 664195
Key indicators
- Single-crystal X-ray study
- T = 113 K
- Mean (C-C) = 0.003 Å
- Disorder in main residue
- R factor = 0.056
- wR factor = 0.134
- Data-to-parameter ratio = 18.0
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.00 Ratio PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.99 Ratio PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.32 Ratio PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.04 Ratio PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.30 Ratio PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.09 Ratio
Alert level C CELLV02_ALERT_1_C The supplied cell volume s.u. differs from that calculated from the cell parameter s.u.'s by > 2 Calculated cell volume su = 15.18 Cell volume su given = 13.00 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 3000 Deg. PLAT213_ALERT_2_C Atom C9' has ADP max/min Ratio ............. 3.10 prola PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C35 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C6 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C24 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C31 PLAT301_ALERT_3_C Main Residue Disorder ......................... 6.00 Perc. PLAT411_ALERT_2_C Short Inter H...H Contact H32 .. H48B .. 2.14 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 18.80 Deg. C11' -C6 -C11 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 22.40 Deg. C9 -C6 -C9' 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 22.80 Deg. C10' -C6 -C10 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 30.00 Deg. C64' -C60 -C64 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 43.30 Deg. C65 -C60 -C65' 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 30.60 Deg. C63 -C60 -C63' 1.555 1.555 1.555
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 96
0 ALERT level A = In general: serious problem 6 ALERT level B = Potentially serious problem 18 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 15 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
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).
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).
For related literature, see: Borzatta & Carrozza (1991); Deng et al. (2006). For synthesis, see: Kaiser & Thurston (1951).
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).
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 | F(000) = 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 = 1.8–27.9° |
α = 105.36 (3)° | µ = 0.21 mm−1 |
β = 96.33 (3)° | T = 113 K |
γ = 96.46 (3)° | 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) |
Confocal monochromator | Rint = 0.035 |
Detector resolution: 7.31 pixels mm-1 | θmax = 27.8°, θmin = 1.5° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) | k = −27→27 |
Tmin = 0.932, Tmax = 0.963 | l = −31→31 |
35937 measured reflections |
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.134 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0532P)2 + 1.4707P] where P = (Fo2 + 2Fc2)/3 |
17590 reflections | (Δ/σ)max = 0.001 |
979 parameters | Δρmax = 0.55 e Å−3 |
96 restraints | Δρmin = −0.53 e Å−3 |
C18H26ClN5 | γ = 96.46 (3)° |
Mr = 347.89 | V = 3831.6 (13) Å3 |
Triclinic, P1 | Z = 8 |
a = 8.0987 (16) Å | Mo Kα radiation |
b = 20.811 (4) Å | µ = 0.21 mm−1 |
c = 23.984 (5) Å | T = 113 K |
α = 105.36 (3)° | 0.34 × 0.32 × 0.18 mm |
β = 96.33 (3)° |
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 > 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) | |
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. |
Experimental details
Crystal data | |
Chemical formula | C18H26ClN5 |
Mr | 347.89 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 113 |
a, b, c (Å) | 8.0987 (16), 20.811 (4), 23.984 (5) |
α, β, γ (°) | 105.36 (3), 96.33 (3), 96.46 (3) |
V (Å3) | 3831.6 (13) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.21 |
Crystal size (mm) | 0.34 × 0.32 × 0.18 |
Data collection | |
Diffractometer | Rigaku Saturn |
Absorption correction | Multi-scan (CrystalClear; Rigaku/MSC, 2005) |
Tmin, Tmax | 0.932, 0.963 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 35937, 17590, 14508 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.656 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.134, 1.08 |
No. of reflections | 17590 |
No. of parameters | 979 |
No. of restraints | 96 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.55, −0.53 |
Computer programs: CrystalClear (Rigaku/MSC, 2005), CrystalClear, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 1996), CrystalStructure (Rigaku/MSC, 2005).
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. |
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).