Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806054018/wk2041sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806054018/wk2041Isup2.hkl |
CCDC reference: 636824
Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2004); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C36H33N3O11 | Z = 2 |
Mr = 683.65 | F(000) = 716 |
Triclinic, P1 | Dx = 1.339 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.5540 (7) Å | Cell parameters from 5868 reflections |
b = 11.1363 (8) Å | θ = 4.3–27.0° |
c = 17.9894 (13) Å | µ = 0.1 mm−1 |
α = 92.746 (6)° | T = 295 K |
β = 94.278 (6)° | Rhomb, colourless |
γ = 96.246 (6)° | 0.6 × 0.4 × 0.25 mm |
V = 1696.0 (2) Å3 |
Xcalibur 2 CCD (Oxford Diffraction) diffractometer | Rint = 0.024 |
ω–2θ scans | θmax = 27.1°, θmin = 4.3° |
13313 measured reflections | h = −10→10 |
7354 independent reflections | k = −14→14 |
4422 reflections with I > 2σ(I) | l = −23→15 |
Refinement on F2 | 55 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.066 | w = 1/[σ2(Fo2) + (0.1153P)2 + 0.3795P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.224 | (Δ/σ)max = 0.001 |
S = 1.06 | Δρmax = 0.29 e Å−3 |
7354 reflections | Δρmin = −0.19 e Å−3 |
456 parameters |
Experimental. 1H NMR (500 MHz, CDCl3): δH 4.12 (3H, s, OMe); 13C NMR (125 MHz, CDCl3) δC 172.5, 171.4, 56.9 (OMe). A solution of 2,4-dichloro-6-methoxy-1,3,5-triazine (72 mg, 0.40 mmol) and methyl 4-benzyloxy-3-hydroxy-5-methoxybenzoate (58 mg, 0.20 mmol) in THF (20 ml) was stirred under nitrogen. N-Methylmorpholine (24 mg, 0.24 mmol) was added and, after stirring for 4 h, the reaction mixture was poured into water and extracted with ethyl acetate. The organic phase was washed successively with a saturated NaHCO3 solution, water, 1 N HCl, water and brine and dried over MgSO4. The crude product was purified by column chromatography on SiO2 (hexane:ethyl acetate = 7:3) to afford compound (I) as a cream white solid (92 mg, 67%). Recrystallization by slow evaporation of a methanol solution of (I) gave the compound as colourless crystals (m.p. 371–373 K). Atom numbering consistent with the crystallographic labelling scheme of Fig. 1 applies to the following characterization data where necessary. 1H NMR (500 MHz, CDCl3): δH 7.51 (2H, d, J = 1.9 Hz, H4/H24), 7.43 (2H, d, J = 1.9 Hz, H2/H22), 7.23–7.25 (10H, m, Ar—H), 5.06 (4H, s, –CH2–), 3.92 (6H, s, COOMe), 3.90 (6H, s, C9-OMe/C29-OMe), 3.77 (3H, s, C206-OMe). 13C NMR (125 MHz, CDCl3) δC 173.6 (C17/C19), 173.0 (C18), 165.9 (C=O), 153.3 (C5/C25), 144.7 (C6/C26), 144.0 (C3/C23) 136.9 (C11/C31), 128.2 (m-C, phenyl), 127.8 (p-C, phenyl), 127.6 (o-C, phenyl), 125.2 (C1/C21), 116.8 (C2/C22), 111.2 (C4/C24), 74.8 (C10/C30), 56.2 (C9/C29), 55.4 (C20), 52.2 (C8/C28). |
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. |
x | y | z | Uiso*/Ueq | ||
O9 | 0.43187 (19) | 0.97507 (17) | 0.10922 (8) | 0.0613 (5) | |
O7 | 0.50934 (19) | 1.20567 (17) | 0.07447 (8) | 0.0600 (5) | |
O5 | 0.76372 (19) | 1.36046 (19) | 0.28891 (9) | 0.0668 (5) | |
N3 | 0.5002 (2) | 1.29663 (19) | 0.29074 (10) | 0.0530 (5) | |
N2 | 0.6378 (2) | 1.28141 (19) | 0.18123 (10) | 0.0551 (5) | |
N1 | 0.3636 (2) | 1.21419 (19) | 0.17642 (10) | 0.0547 (5) | |
C21 | 0.3821 (3) | 1.1353 (2) | 0.03427 (11) | 0.0523 (6) | |
C26 | 0.3459 (3) | 1.0163 (2) | 0.05108 (11) | 0.0521 (6) | |
C19 | 0.5005 (3) | 1.2336 (2) | 0.14758 (11) | 0.0504 (5) | |
O6 | 0.2428 (2) | 1.2356 (2) | 0.28547 (10) | 0.0757 (6) | |
O4 | 0.6346 (3) | 1.56798 (19) | 0.31551 (9) | 0.0752 (6) | |
C17 | 0.6251 (3) | 1.3115 (2) | 0.25289 (12) | 0.0516 (5) | |
C23 | 0.1970 (3) | 1.1110 (3) | −0.07233 (12) | 0.0571 (6) | |
O3 | 0.6314 (3) | 1.66590 (18) | 0.45795 (10) | 0.0742 (5) | |
C25 | 0.2291 (3) | 0.9430 (2) | 0.00470 (12) | 0.0542 (6) | |
C18 | 0.3720 (3) | 1.2480 (2) | 0.24842 (12) | 0.0539 (6) | |
C3 | 0.8256 (3) | 1.3919 (3) | 0.49222 (13) | 0.0593 (6) | |
O8 | 0.1982 (2) | 0.82689 (19) | 0.02396 (10) | 0.0719 (5) | |
C2 | 0.8244 (3) | 1.3444 (3) | 0.41953 (13) | 0.0601 (6) | |
H2 | 0.868 | 1.273 | 0.4093 | 0.072* | |
C1 | 0.7573 (3) | 1.4052 (3) | 0.36288 (13) | 0.0579 (6) | |
C4 | 0.7611 (3) | 1.4979 (2) | 0.50708 (12) | 0.0569 (6) | |
H4 | 0.7623 | 1.5284 | 0.5562 | 0.068* | |
C5 | 0.6944 (3) | 1.5596 (2) | 0.44974 (13) | 0.0565 (6) | |
C22 | 0.3102 (3) | 1.1846 (2) | −0.02664 (12) | 0.0574 (6) | |
H22 | 0.337 | 1.265 | −0.0368 | 0.069* | |
C6 | 0.6920 (3) | 1.5113 (2) | 0.37585 (12) | 0.0574 (6) | |
O10 | 0.0382 (3) | 1.0929 (2) | −0.18775 (12) | 0.0909 (7) | |
C24 | 0.1578 (3) | 0.9921 (3) | −0.05680 (13) | 0.0596 (6) | |
H24 | 0.0823 | 0.9438 | −0.0881 | 0.072* | |
C27 | 0.1194 (3) | 1.1560 (3) | −0.14049 (15) | 0.0690 (8) | |
O2 | 0.9539 (3) | 1.2276 (2) | 0.53254 (12) | 0.0915 (7) | |
O1 | 0.9036 (3) | 1.3654 (3) | 0.61981 (11) | 0.0972 (7) | |
O11 | 0.1497 (3) | 1.2749 (2) | −0.14429 (12) | 0.0912 (7) | |
C30 | 0.3501 (4) | 0.9087 (3) | 0.16347 (14) | 0.0748 (8) | |
H30A | 0.3448 | 0.8226 | 0.1508 | 0.09* | |
H30B | 0.2431 | 0.93 | 0.1637 | 0.09* | |
C36 | 0.5928 (3) | 0.9801 (3) | 0.24941 (15) | 0.0713 (8) | |
H36 | 0.6507 | 0.9922 | 0.2081 | 0.086* | |
C31 | 0.4354 (3) | 0.9379 (3) | 0.23940 (13) | 0.0620 (6) | |
C9 | 0.6291 (4) | 1.7177 (3) | 0.53138 (15) | 0.0866 (9) | |
H9A | 0.5714 | 1.6615 | 0.5609 | 0.13* | |
H9B | 0.5792 | 1.7908 | 0.5295 | 0.13* | |
H9C | 0.7353 | 1.736 | 0.5534 | 0.13* | |
C11 | 0.3976 (5) | 1.5615 (3) | 0.23491 (17) | 0.0830 (9) | |
C29 | 0.1003 (4) | 0.7446 (3) | −0.02769 (17) | 0.0784 (8) | |
H29A | −0.0023 | 0.7717 | −0.0348 | 0.118* | |
H29B | 0.0907 | 0.6655 | −0.0084 | 0.118* | |
H29C | 0.1466 | 0.7415 | −0.0746 | 0.118* | |
C7 | 0.8969 (3) | 1.3297 (3) | 0.55562 (15) | 0.0702 (8) | |
C10 | 0.4734 (4) | 1.5952 (3) | 0.31184 (16) | 0.0850 (9) | |
H10A | 0.4705 | 1.6808 | 0.3236 | 0.102* | |
H10B | 0.4162 | 1.5502 | 0.3481 | 0.102* | |
C35 | 0.6653 (4) | 1.0046 (3) | 0.32016 (18) | 0.0861 (9) | |
H35 | 0.7717 | 1.0342 | 0.3262 | 0.103* | |
C20 | 0.0956 (4) | 1.1851 (5) | 0.2452 (2) | 0.1134 (15) | |
H20A | 0.0697 | 1.2359 | 0.2055 | 0.17* | |
H20B | 0.0131 | 1.1805 | 0.2787 | 0.17* | |
H20C | 0.1063 | 1.1055 | 0.2248 | 0.17* | |
C32 | 0.3533 (4) | 0.9201 (4) | 0.30148 (16) | 0.0911 (10) | |
H32 | 0.2468 | 0.8911 | 0.2958 | 0.109* | |
C14 | 0.2542 (8) | 1.4961 (4) | 0.0923 (3) | 0.1370 (19) | |
H14 | 0.206 | 1.4743 | 0.0448 | 0.164* | |
C8 | 1.0329 (5) | 1.1636 (4) | 0.5890 (2) | 0.1075 (13) | |
H8A | 1.1308 | 1.2099 | 0.6069 | 0.161* | |
H8B | 1.0534 | 1.0865 | 0.568 | 0.161* | |
H8C | 0.9672 | 1.1517 | 0.6296 | 0.161* | |
C12 | 0.2436 (5) | 1.5122 (4) | 0.2244 (2) | 0.1117 (13) | |
H12 | 0.1854 | 1.5003 | 0.2656 | 0.134* | |
C16 | 0.4774 (7) | 1.5768 (5) | 0.1725 (2) | 0.143 (2) | |
H16 | 0.5825 | 1.6099 | 0.1775 | 0.172* | |
C28 | 0.0851 (5) | 1.3247 (5) | −0.2123 (2) | 0.1219 (15) | |
H28A | 0.1289 | 1.2899 | −0.2548 | 0.183* | |
H28B | 0.1115 | 1.4109 | −0.2095 | 0.183* | |
H28C | −0.0276 | 1.3059 | −0.2171 | 0.183* | |
C13 | 0.1726 (7) | 1.4797 (5) | 0.1536 (3) | 0.143 (2) | |
H13 | 0.0677 | 1.4463 | 0.1479 | 0.172* | |
C34 | 0.5832 (5) | 0.9860 (4) | 0.38163 (17) | 0.0925 (10) | |
H34 | 0.6334 | 1.0012 | 0.4293 | 0.111* | |
C33 | 0.4278 (5) | 0.9451 (4) | 0.37229 (17) | 0.1019 (12) | |
H33 | 0.3706 | 0.9337 | 0.4139 | 0.122* | |
C15 | 0.4049 (9) | 1.5441 (5) | 0.1013 (2) | 0.159 (2) | |
H15 | 0.462 | 1.5558 | 0.0597 | 0.191* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O9 | 0.0537 (9) | 0.0918 (13) | 0.0415 (8) | 0.0190 (9) | 0.0062 (7) | 0.0072 (8) |
O7 | 0.0572 (10) | 0.0863 (12) | 0.0351 (8) | 0.0023 (8) | 0.0080 (7) | −0.0051 (7) |
O5 | 0.0518 (10) | 0.1025 (14) | 0.0440 (9) | 0.0056 (9) | 0.0056 (7) | −0.0138 (9) |
N3 | 0.0528 (11) | 0.0686 (13) | 0.0385 (9) | 0.0139 (9) | 0.0036 (8) | −0.0048 (8) |
N2 | 0.0511 (11) | 0.0744 (14) | 0.0396 (9) | 0.0062 (9) | 0.0072 (8) | −0.0027 (9) |
N1 | 0.0521 (11) | 0.0715 (13) | 0.0412 (10) | 0.0136 (9) | 0.0053 (8) | −0.0071 (9) |
C21 | 0.0467 (12) | 0.0743 (17) | 0.0365 (10) | 0.0113 (11) | 0.0071 (9) | −0.0078 (10) |
C26 | 0.0468 (12) | 0.0782 (17) | 0.0337 (10) | 0.0184 (11) | 0.0068 (8) | −0.0034 (10) |
C19 | 0.0530 (13) | 0.0634 (14) | 0.0363 (10) | 0.0148 (10) | 0.0049 (9) | −0.0007 (9) |
O6 | 0.0535 (10) | 0.1190 (16) | 0.0528 (10) | 0.0075 (10) | 0.0132 (8) | −0.0203 (10) |
O4 | 0.0914 (14) | 0.0913 (14) | 0.0434 (9) | 0.0097 (11) | 0.0055 (9) | 0.0108 (9) |
C17 | 0.0486 (12) | 0.0645 (15) | 0.0422 (11) | 0.0104 (10) | 0.0039 (9) | −0.0021 (10) |
C23 | 0.0499 (13) | 0.0804 (18) | 0.0433 (12) | 0.0181 (12) | 0.0055 (10) | −0.0009 (11) |
O3 | 0.1020 (15) | 0.0717 (12) | 0.0478 (10) | 0.0098 (11) | 0.0045 (9) | −0.0041 (8) |
C25 | 0.0524 (13) | 0.0682 (16) | 0.0434 (11) | 0.0111 (11) | 0.0104 (10) | −0.0027 (10) |
C18 | 0.0523 (13) | 0.0700 (16) | 0.0412 (11) | 0.0172 (11) | 0.0064 (9) | −0.0043 (10) |
C3 | 0.0478 (13) | 0.0799 (18) | 0.0467 (12) | −0.0044 (12) | −0.0026 (10) | 0.0049 (11) |
O8 | 0.0805 (13) | 0.0774 (13) | 0.0550 (10) | 0.0033 (10) | −0.0013 (9) | −0.0021 (9) |
C2 | 0.0483 (13) | 0.0777 (17) | 0.0524 (13) | 0.0042 (11) | 0.0008 (10) | −0.0032 (12) |
C1 | 0.0476 (12) | 0.0812 (18) | 0.0424 (12) | −0.0001 (12) | 0.0037 (9) | −0.0067 (11) |
C4 | 0.0537 (13) | 0.0733 (17) | 0.0396 (11) | −0.0068 (12) | 0.0011 (9) | −0.0025 (10) |
C5 | 0.0591 (14) | 0.0619 (15) | 0.0453 (12) | −0.0049 (11) | 0.0047 (10) | −0.0021 (10) |
C22 | 0.0610 (14) | 0.0718 (16) | 0.0412 (11) | 0.0174 (12) | 0.0067 (10) | −0.0035 (11) |
C6 | 0.0584 (14) | 0.0738 (17) | 0.0367 (11) | −0.0038 (12) | 0.0000 (10) | 0.0013 (10) |
O10 | 0.0735 (13) | 0.132 (2) | 0.0648 (12) | 0.0167 (12) | −0.0182 (10) | 0.0031 (12) |
C24 | 0.0486 (13) | 0.0853 (19) | 0.0442 (12) | 0.0097 (12) | 0.0038 (10) | −0.0084 (12) |
C27 | 0.0535 (14) | 0.103 (2) | 0.0531 (14) | 0.0220 (15) | 0.0027 (12) | 0.0042 (15) |
O2 | 0.0896 (15) | 0.1150 (19) | 0.0738 (13) | 0.0322 (13) | −0.0054 (11) | 0.0175 (12) |
O1 | 0.0969 (16) | 0.145 (2) | 0.0520 (11) | 0.0264 (14) | −0.0045 (10) | 0.0155 (12) |
O11 | 0.0956 (16) | 0.1089 (19) | 0.0720 (13) | 0.0271 (13) | −0.0077 (11) | 0.0216 (12) |
C30 | 0.0783 (19) | 0.098 (2) | 0.0466 (13) | 0.0021 (16) | 0.0043 (12) | 0.0107 (13) |
C36 | 0.0656 (17) | 0.098 (2) | 0.0543 (14) | 0.0226 (15) | 0.0036 (12) | 0.0122 (14) |
C31 | 0.0659 (16) | 0.0771 (18) | 0.0460 (12) | 0.0190 (13) | 0.0043 (11) | 0.0091 (11) |
C9 | 0.119 (3) | 0.085 (2) | 0.0542 (16) | 0.0052 (18) | 0.0163 (16) | −0.0124 (14) |
C11 | 0.117 (3) | 0.0700 (19) | 0.0608 (16) | 0.0226 (17) | −0.0187 (16) | 0.0039 (14) |
C29 | 0.0793 (19) | 0.084 (2) | 0.0671 (17) | −0.0049 (15) | 0.0026 (14) | −0.0084 (15) |
C7 | 0.0511 (14) | 0.100 (2) | 0.0583 (16) | 0.0027 (14) | 0.0004 (11) | 0.0124 (15) |
C10 | 0.101 (2) | 0.103 (2) | 0.0528 (15) | 0.0336 (19) | −0.0105 (15) | −0.0004 (15) |
C35 | 0.0730 (19) | 0.112 (3) | 0.0737 (19) | 0.0181 (17) | −0.0129 (15) | 0.0184 (18) |
C20 | 0.0517 (17) | 0.199 (5) | 0.082 (2) | −0.004 (2) | 0.0147 (15) | −0.042 (2) |
C32 | 0.081 (2) | 0.140 (3) | 0.0530 (16) | 0.009 (2) | 0.0127 (14) | 0.0110 (17) |
C14 | 0.213 (5) | 0.103 (3) | 0.086 (3) | 0.038 (3) | −0.066 (3) | −0.018 (2) |
C8 | 0.091 (2) | 0.138 (3) | 0.102 (3) | 0.038 (2) | 0.003 (2) | 0.044 (2) |
C12 | 0.105 (3) | 0.135 (4) | 0.093 (2) | 0.043 (2) | −0.021 (2) | −0.025 (2) |
C16 | 0.199 (5) | 0.159 (4) | 0.0511 (18) | −0.062 (4) | −0.015 (2) | 0.009 (2) |
C28 | 0.123 (3) | 0.154 (4) | 0.096 (3) | 0.048 (3) | −0.017 (2) | 0.046 (3) |
C13 | 0.131 (4) | 0.165 (5) | 0.127 (4) | 0.055 (3) | −0.054 (3) | −0.056 (3) |
C34 | 0.116 (3) | 0.110 (3) | 0.0515 (16) | 0.028 (2) | −0.0146 (17) | 0.0078 (16) |
C33 | 0.111 (3) | 0.150 (4) | 0.0485 (16) | 0.021 (3) | 0.0149 (17) | 0.0110 (18) |
C15 | 0.259 (6) | 0.139 (4) | 0.057 (2) | −0.052 (4) | −0.025 (3) | 0.012 (2) |
O9—C26 | 1.361 (3) | C30—C31 | 1.504 (4) |
O9—C30 | 1.431 (3) | C30—H30A | 0.97 |
O7—C19 | 1.346 (2) | C30—H30B | 0.97 |
O7—C21 | 1.401 (3) | C36—C31 | 1.373 (4) |
O5—C17 | 1.354 (3) | C36—C35 | 1.375 (4) |
O5—C1 | 1.405 (3) | C36—H36 | 0.93 |
N3—C17 | 1.309 (3) | C31—C32 | 1.374 (4) |
N3—C18 | 1.335 (3) | C9—H9A | 0.96 |
N2—C19 | 1.325 (3) | C9—H9B | 0.96 |
N2—C17 | 1.331 (3) | C9—H9C | 0.96 |
N1—C19 | 1.317 (3) | C11—C16 | 1.366 (6) |
N1—C18 | 1.326 (3) | C11—C12 | 1.367 (6) |
C21—C26 | 1.380 (4) | C11—C10 | 1.497 (4) |
C21—C22 | 1.382 (3) | C29—H29A | 0.96 |
C26—C25 | 1.412 (3) | C29—H29B | 0.96 |
O6—C18 | 1.331 (3) | C29—H29C | 0.96 |
O6—C20 | 1.448 (4) | C10—H10A | 0.97 |
O4—C6 | 1.368 (3) | C10—H10B | 0.97 |
O4—C10 | 1.441 (4) | C35—C34 | 1.366 (5) |
C23—C24 | 1.377 (4) | C35—H35 | 0.93 |
C23—C22 | 1.389 (4) | C20—H20A | 0.96 |
C23—C27 | 1.485 (4) | C20—H20B | 0.96 |
O3—C5 | 1.359 (3) | C20—H20C | 0.96 |
O3—C9 | 1.418 (3) | C32—C33 | 1.383 (4) |
C25—O8 | 1.358 (3) | C32—H32 | 0.93 |
C25—C24 | 1.387 (3) | C14—C15 | 1.336 (8) |
C3—C4 | 1.379 (4) | C14—C13 | 1.357 (8) |
C3—C2 | 1.386 (3) | C14—H14 | 0.93 |
C3—C7 | 1.489 (4) | C8—H8A | 0.96 |
O8—C29 | 1.428 (3) | C8—H8B | 0.96 |
C2—C1 | 1.375 (4) | C8—H8C | 0.96 |
C2—H2 | 0.93 | C12—C13 | 1.383 (5) |
C1—C6 | 1.379 (4) | C12—H12 | 0.93 |
C4—C5 | 1.389 (3) | C16—C15 | 1.394 (5) |
C4—H4 | 0.93 | C16—H16 | 0.93 |
C5—C6 | 1.408 (3) | C28—H28A | 0.96 |
C22—H22 | 0.93 | C28—H28B | 0.96 |
O10—C27 | 1.203 (3) | C28—H28C | 0.96 |
C24—H24 | 0.93 | C13—H13 | 0.93 |
C27—O11 | 1.328 (4) | C34—C33 | 1.352 (5) |
O2—C7 | 1.344 (4) | C34—H34 | 0.93 |
O2—C8 | 1.438 (4) | C33—H33 | 0.93 |
O1—C7 | 1.198 (3) | C15—H15 | 0.93 |
O11—C28 | 1.463 (4) | ||
C26—O9—C30 | 118.52 (19) | C32—C31—C30 | 118.8 (3) |
C19—O7—C21 | 119.18 (17) | O3—C9—H9A | 109.5 |
C17—O5—C1 | 116.27 (18) | O3—C9—H9B | 109.5 |
C17—N3—C18 | 112.43 (18) | H9A—C9—H9B | 109.5 |
C19—N2—C17 | 111.43 (19) | O3—C9—H9C | 109.5 |
C19—N1—C18 | 112.6 (2) | H9A—C9—H9C | 109.5 |
C26—C21—C22 | 122.6 (2) | H9B—C9—H9C | 109.5 |
C26—C21—O7 | 119.3 (2) | C16—C11—C12 | 116.9 (3) |
C22—C21—O7 | 117.7 (2) | C16—C11—C10 | 122.4 (4) |
O9—C26—C21 | 117.5 (2) | C12—C11—C10 | 120.7 (3) |
O9—C26—C25 | 123.9 (2) | O8—C29—H29A | 109.5 |
C21—C26—C25 | 118.5 (2) | O8—C29—H29B | 109.5 |
N1—C19—N2 | 128.26 (19) | H29A—C29—H29B | 109.5 |
N1—C19—O7 | 119.2 (2) | O8—C29—H29C | 109.5 |
N2—C19—O7 | 112.53 (19) | H29A—C29—H29C | 109.5 |
C18—O6—C20 | 118.4 (2) | H29B—C29—H29C | 109.5 |
C6—O4—C10 | 119.0 (2) | O1—C7—O2 | 123.4 (3) |
N3—C17—N2 | 128.4 (2) | O1—C7—C3 | 124.6 (3) |
N3—C17—O5 | 118.73 (19) | O2—C7—C3 | 112.0 (2) |
N2—C17—O5 | 112.86 (19) | O4—C10—C11 | 109.2 (3) |
C24—C23—C22 | 120.5 (2) | O4—C10—H10A | 109.8 |
C24—C23—C27 | 118.1 (2) | C11—C10—H10A | 109.8 |
C22—C23—C27 | 121.4 (3) | O4—C10—H10B | 109.8 |
C5—O3—C9 | 117.8 (2) | C11—C10—H10B | 109.8 |
O8—C25—C24 | 125.1 (2) | H10A—C10—H10B | 108.3 |
O8—C25—C26 | 115.9 (2) | C34—C35—C36 | 120.8 (3) |
C24—C25—C26 | 119.0 (2) | C34—C35—H35 | 119.6 |
N1—C18—O6 | 119.8 (2) | C36—C35—H35 | 119.6 |
N1—C18—N3 | 126.9 (2) | O6—C20—H20A | 109.5 |
O6—C18—N3 | 113.28 (19) | O6—C20—H20B | 109.5 |
C4—C3—C2 | 120.5 (2) | H20A—C20—H20B | 109.5 |
C4—C3—C7 | 118.8 (2) | O6—C20—H20C | 109.5 |
C2—C3—C7 | 120.6 (3) | H20A—C20—H20C | 109.5 |
C25—O8—C29 | 117.7 (2) | H20B—C20—H20C | 109.5 |
C1—C2—C3 | 118.5 (3) | C31—C32—C33 | 120.6 (3) |
C1—C2—H2 | 120.8 | C31—C32—H32 | 119.7 |
C3—C2—H2 | 120.8 | C33—C32—H32 | 119.7 |
C2—C1—C6 | 122.4 (2) | C15—C14—C13 | 118.9 (4) |
C2—C1—O5 | 118.4 (2) | C15—C14—H14 | 120.5 |
C6—C1—O5 | 119.1 (2) | C13—C14—H14 | 120.5 |
C3—C4—C5 | 120.9 (2) | O2—C8—H8A | 109.5 |
C3—C4—H4 | 119.5 | O2—C8—H8B | 109.5 |
C5—C4—H4 | 119.5 | H8A—C8—H8B | 109.5 |
O3—C5—C4 | 125.7 (2) | O2—C8—H8C | 109.5 |
O3—C5—C6 | 115.6 (2) | H8A—C8—H8C | 109.5 |
C4—C5—C6 | 118.7 (2) | H8B—C8—H8C | 109.5 |
C21—C22—C23 | 118.3 (3) | C11—C12—C13 | 121.3 (5) |
C21—C22—H22 | 120.8 | C11—C12—H12 | 119.3 |
C23—C22—H22 | 120.8 | C13—C12—H12 | 119.3 |
O4—C6—C1 | 118.0 (2) | C11—C16—C15 | 121.5 (5) |
O4—C6—C5 | 122.9 (2) | C11—C16—H16 | 119.3 |
C1—C6—C5 | 118.9 (2) | C15—C16—H16 | 119.3 |
C23—C24—C25 | 121.2 (2) | O11—C28—H28A | 109.5 |
C23—C24—H24 | 119.4 | O11—C28—H28B | 109.5 |
C25—C24—H24 | 119.4 | H28A—C28—H28B | 109.5 |
O10—C27—O11 | 122.9 (3) | O11—C28—H28C | 109.5 |
O10—C27—C23 | 124.5 (3) | H28A—C28—H28C | 109.5 |
O11—C27—C23 | 112.6 (2) | H28B—C28—H28C | 109.5 |
C7—O2—C8 | 116.6 (3) | C14—C13—C12 | 120.8 (5) |
C27—O11—C28 | 115.6 (3) | C14—C13—H13 | 119.6 |
O9—C30—C31 | 109.5 (2) | C12—C13—H13 | 119.6 |
O9—C30—H30A | 109.8 | C33—C34—C35 | 119.2 (3) |
C31—C30—H30A | 109.8 | C33—C34—H34 | 120.4 |
O9—C30—H30B | 109.8 | C35—C34—H34 | 120.4 |
C31—C30—H30B | 109.8 | C34—C33—C32 | 120.6 (3) |
H30A—C30—H30B | 108.2 | C34—C33—H33 | 119.7 |
C31—C36—C35 | 120.4 (3) | C32—C33—H33 | 119.7 |
C31—C36—H36 | 119.8 | C14—C15—C16 | 120.6 (5) |
C35—C36—H36 | 119.8 | C14—C15—H15 | 119.7 |
C36—C31—C32 | 118.5 (3) | C16—C15—H15 | 119.7 |
C36—C31—C30 | 122.7 (2) | ||
C19—O7—C21—C26 | −66.6 (3) | C10—O4—C6—C1 | 124.9 (3) |
C19—O7—C21—C22 | 121.0 (2) | C10—O4—C6—C5 | −58.4 (3) |
C30—O9—C26—C21 | 132.6 (2) | C2—C1—C6—O4 | 177.0 (2) |
C30—O9—C26—C25 | −51.3 (3) | O5—C1—C6—O4 | 0.6 (3) |
C22—C21—C26—O9 | 175.42 (19) | C2—C1—C6—C5 | 0.2 (4) |
O7—C21—C26—O9 | 3.3 (3) | O5—C1—C6—C5 | −176.2 (2) |
C22—C21—C26—C25 | −0.9 (3) | O3—C5—C6—O4 | 1.8 (4) |
O7—C21—C26—C25 | −172.99 (18) | C4—C5—C6—O4 | −177.3 (2) |
C18—N1—C19—N2 | −0.4 (4) | O3—C5—C6—C1 | 178.4 (2) |
C18—N1—C19—O7 | −178.8 (2) | C4—C5—C6—C1 | −0.7 (4) |
C17—N2—C19—N1 | −0.3 (4) | C22—C23—C24—C25 | 0.4 (3) |
C17—N2—C19—O7 | 178.2 (2) | C27—C23—C24—C25 | 178.1 (2) |
C21—O7—C19—N1 | −12.5 (3) | O8—C25—C24—C23 | −179.7 (2) |
C21—O7—C19—N2 | 168.8 (2) | C26—C25—C24—C23 | −1.2 (3) |
C18—N3—C17—N2 | −2.1 (4) | C24—C23—C27—O10 | −8.8 (4) |
C18—N3—C17—O5 | 179.8 (2) | C22—C23—C27—O10 | 168.8 (3) |
C19—N2—C17—N3 | 1.7 (4) | C24—C23—C27—O11 | 171.4 (2) |
C19—N2—C17—O5 | 179.9 (2) | C22—C23—C27—O11 | −10.9 (3) |
C1—O5—C17—N3 | −7.5 (3) | O10—C27—O11—C28 | −3.4 (4) |
C1—O5—C17—N2 | 174.1 (2) | C23—C27—O11—C28 | 176.4 (3) |
O9—C26—C25—O8 | 4.0 (3) | C26—O9—C30—C31 | −144.7 (2) |
C21—C26—C25—O8 | −179.92 (19) | C35—C36—C31—C32 | −0.4 (5) |
O9—C26—C25—C24 | −174.65 (19) | C35—C36—C31—C30 | −179.6 (3) |
C21—C26—C25—C24 | 1.4 (3) | O9—C30—C31—C36 | −23.6 (4) |
C19—N1—C18—O6 | 179.2 (2) | O9—C30—C31—C32 | 157.3 (3) |
C19—N1—C18—N3 | −0.2 (4) | C8—O2—C7—O1 | −3.1 (5) |
C20—O6—C18—N1 | −0.1 (4) | C8—O2—C7—C3 | 176.9 (3) |
C20—O6—C18—N3 | 179.3 (3) | C4—C3—C7—O1 | −0.4 (4) |
C17—N3—C18—N1 | 1.3 (4) | C2—C3—C7—O1 | 179.4 (3) |
C17—N3—C18—O6 | −178.1 (2) | C4—C3—C7—O2 | 179.6 (2) |
C24—C25—O8—C29 | 8.4 (4) | C2—C3—C7—O2 | −0.5 (3) |
C26—C25—O8—C29 | −170.1 (2) | C6—O4—C10—C11 | −135.2 (3) |
C4—C3—C2—C1 | −0.1 (4) | C16—C11—C10—O4 | −36.9 (5) |
C7—C3—C2—C1 | −179.9 (2) | C12—C11—C10—O4 | 142.4 (3) |
C3—C2—C1—C6 | 0.2 (4) | C31—C36—C35—C34 | 0.9 (5) |
C3—C2—C1—O5 | 176.6 (2) | C36—C31—C32—C33 | 0.4 (5) |
C17—O5—C1—C2 | 110.3 (3) | C30—C31—C32—C33 | 179.6 (3) |
C17—O5—C1—C6 | −73.2 (3) | C16—C11—C12—C13 | −0.1 (6) |
C2—C3—C4—C5 | −0.3 (4) | C10—C11—C12—C13 | −179.4 (4) |
C7—C3—C4—C5 | 179.5 (2) | C12—C11—C16—C15 | 0.2 (7) |
C9—O3—C5—C4 | −1.8 (4) | C10—C11—C16—C15 | 179.6 (5) |
C9—O3—C5—C6 | 179.2 (2) | C15—C14—C13—C12 | 0.1 (8) |
C3—C4—C5—O3 | −178.3 (2) | C11—C12—C13—C14 | −0.1 (7) |
C3—C4—C5—C6 | 0.7 (4) | C36—C35—C34—C33 | −1.3 (6) |
C26—C21—C22—C23 | 0.1 (3) | C35—C34—C33—C32 | 1.2 (6) |
O7—C21—C22—C23 | 172.3 (2) | C31—C32—C33—C34 | −0.8 (6) |
C24—C23—C22—C21 | 0.2 (3) | C13—C14—C15—C16 | 0.0 (9) |
C27—C23—C22—C21 | −177.4 (2) | C11—C16—C15—C14 | −0.2 (9) |
D—H···A | D—H | H···A | D···A | D—H···A |
C20—H20C···O10i | 0.96 | 2.45 | 3.272 (6) | 144 |
C30—H30B···O10i | 0.97 | 2.46 | 3.381 (4) | 157 |
Symmetry code: (i) −x, −y+2, −z. |