Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803020348/cv6234sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803020348/cv6234Isup2.hkl |
CCDC reference: 226944
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
C36H28Cl4N2O5·CHCl3·0.5CH4O | Z = 2 |
Mr = 845.79 | F(000) = 866 |
Triclinic, P1 | Dx = 1.443 Mg m−3 |
Hall symbol: -P 1 | Melting point = 521–522 K |
a = 11.293 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.955 (4) Å | Cell parameters from 956 reflections |
c = 15.027 (4) Å | θ = 3.5–23.5° |
α = 114.946 (4)° | µ = 0.56 mm−1 |
β = 96.953 (5)° | T = 293 K |
γ = 96.393 (5)° | Block, colorless |
V = 1946.2 (10) Å3 | 0.38 × 0.36 × 0.28 mm |
Bruker SMART CCD area-detector diffractometer | 6824 independent reflections |
Radiation source: fine-focus sealed tube | 4415 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
φ and ω scans | θmax = 25.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −13→13 |
Tmin = 0.732, Tmax = 0.856 | k = −13→15 |
10073 measured reflections | l = −17→10 |
Refinement on F2 | 1 restraint |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.068 | w = 1/[σ2(Fo2) + (0.084P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.232 | (Δ/σ)max < 0.001 |
S = 1.03 | Δρmax = 0.64 e Å−3 |
6824 reflections | Δρmin = −0.77 e Å−3 |
480 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 | −0.22458 (14) | 0.49499 (12) | 0.11480 (12) | 0.0782 (4) | |
Cl2 | −0.36036 (14) | 0.88541 (14) | 0.11735 (12) | 0.0831 (5) | |
Cl3 | 0.31732 (16) | 1.34688 (13) | 0.46191 (11) | 0.0914 (5) | |
Cl4 | −0.09293 (14) | 1.02722 (17) | 0.35206 (14) | 0.0962 (5) | |
N1 | −0.0862 (3) | 0.7395 (3) | 0.1614 (2) | 0.0439 (8) | |
N2 | 0.1180 (3) | 1.1893 (3) | 0.2564 (3) | 0.0496 (9) | |
O1 | −0.0800 (3) | 0.9843 (2) | 0.0931 (2) | 0.0514 (7) | |
O2 | 0.0202 (2) | 0.7709 (2) | 0.1308 (2) | 0.0429 (7) | |
O3 | −0.2306 (4) | 0.3279 (3) | −0.3501 (2) | 0.0710 (10) | |
O4 | 0.1361 (3) | 1.1193 (2) | 0.1592 (2) | 0.0476 (7) | |
O5 | 0.6309 (3) | 0.9759 (4) | 0.3962 (3) | 0.0730 (10) | |
C1 | 0.0021 (3) | 0.9346 (3) | 0.0962 (3) | 0.0350 (8) | |
C2 | −0.0150 (3) | 0.8014 (3) | 0.0488 (3) | 0.0369 (8) | |
C3 | 0.0753 (4) | 0.7636 (4) | −0.0215 (3) | 0.0490 (10) | |
H3A | 0.0681 | 0.6801 | −0.0505 | 0.059* | |
H3B | 0.0570 | 0.7852 | −0.0754 | 0.059* | |
C4 | 0.2040 (4) | 0.8205 (4) | 0.0351 (3) | 0.0491 (10) | |
H4A | 0.2218 | 0.7983 | 0.0887 | 0.059* | |
H4B | 0.2605 | 0.7928 | −0.0098 | 0.059* | |
C5 | 0.2221 (4) | 0.9503 (4) | 0.0783 (3) | 0.0438 (9) | |
H5A | 0.2132 | 0.9726 | 0.0242 | 0.053* | |
H5B | 0.3041 | 0.9826 | 0.1162 | 0.053* | |
C6 | 0.1326 (3) | 1.0016 (3) | 0.1464 (3) | 0.0382 (9) | |
C7 | −0.1496 (3) | 0.7436 (3) | 0.0086 (3) | 0.0369 (8) | |
H7 | −0.1964 | 0.7991 | −0.0001 | 0.044* | |
C8 | −0.1783 (3) | 0.7262 (3) | 0.0977 (3) | 0.0394 (9) | |
C9 | −0.3001 (4) | 0.6861 (4) | 0.1111 (3) | 0.0465 (10) | |
C10 | −0.3302 (4) | 0.5837 (4) | 0.1190 (3) | 0.0582 (12) | |
C11 | −0.4454 (5) | 0.5472 (6) | 0.1301 (4) | 0.0783 (17) | |
H11 | −0.4626 | 0.4784 | 0.1354 | 0.094* | |
C12 | −0.5329 (5) | 0.6118 (7) | 0.1331 (4) | 0.088 (2) | |
H12 | −0.6105 | 0.5861 | 0.1390 | 0.105* | |
C13 | −0.5072 (5) | 0.7153 (7) | 0.1276 (4) | 0.0804 (18) | |
H13 | −0.5670 | 0.7601 | 0.1308 | 0.096* | |
C14 | −0.3919 (4) | 0.7523 (5) | 0.1172 (3) | 0.0585 (12) | |
C15 | −0.1772 (3) | 0.6322 (3) | −0.0865 (3) | 0.0369 (8) | |
C16 | −0.2437 (4) | 0.6257 (4) | −0.1719 (3) | 0.0469 (10) | |
H16 | −0.2761 | 0.6895 | −0.1697 | 0.056* | |
C17 | −0.2639 (4) | 0.5259 (4) | −0.2619 (3) | 0.0545 (11) | |
H17 | −0.3083 | 0.5237 | −0.3192 | 0.065* | |
C18 | −0.2179 (4) | 0.4305 (4) | −0.2656 (3) | 0.0484 (10) | |
C19 | −0.1537 (4) | 0.4339 (4) | −0.1808 (3) | 0.0477 (10) | |
H19 | −0.1235 | 0.3691 | −0.1830 | 0.057* | |
C20 | −0.1337 (4) | 0.5337 (4) | −0.0917 (3) | 0.0452 (10) | |
H20 | −0.0906 | 0.5349 | −0.0343 | 0.054* | |
C21 | −0.2875 (8) | 0.3205 (6) | −0.4423 (4) | 0.107 (2) | |
H21A | −0.3691 | 0.3339 | −0.4385 | 0.161* | |
H21B | −0.2889 | 0.2449 | −0.4945 | 0.161* | |
H21C | −0.2432 | 0.3778 | −0.4565 | 0.161* | |
C22 | 0.1580 (3) | 1.0144 (3) | 0.2553 (3) | 0.0373 (8) | |
H22 | 0.0980 | 0.9581 | 0.2614 | 0.045* | |
C23 | 0.1279 (4) | 1.1338 (3) | 0.3083 (3) | 0.0423 (9) | |
C24 | 0.1128 (4) | 1.1867 (4) | 0.4140 (3) | 0.0532 (11) | |
C25 | 0.1923 (6) | 1.2829 (4) | 0.4895 (4) | 0.0685 (14) | |
C26 | 0.1762 (8) | 1.3301 (6) | 0.5878 (4) | 0.091 (2) | |
H26 | 0.2300 | 1.3943 | 0.6366 | 0.110* | |
C27 | 0.0801 (9) | 1.2805 (8) | 0.6114 (5) | 0.107 (3) | |
H27 | 0.0702 | 1.3107 | 0.6776 | 0.129* | |
C28 | −0.0031 (7) | 1.1870 (7) | 0.5406 (5) | 0.093 (2) | |
H28 | −0.0695 | 1.1556 | 0.5580 | 0.111* | |
C29 | 0.0151 (5) | 1.1412 (5) | 0.4425 (4) | 0.0673 (14) | |
C30 | 0.2832 (3) | 1.0044 (3) | 0.2951 (3) | 0.0372 (9) | |
C31 | 0.2993 (4) | 0.9149 (3) | 0.3194 (3) | 0.0416 (9) | |
H31 | 0.2318 | 0.8623 | 0.3130 | 0.050* | |
C32 | 0.4139 (4) | 0.9014 (4) | 0.3534 (3) | 0.0494 (10) | |
H32 | 0.4228 | 0.8399 | 0.3687 | 0.059* | |
C33 | 0.5146 (4) | 0.9795 (4) | 0.3642 (3) | 0.0503 (11) | |
C34 | 0.4993 (4) | 1.0699 (4) | 0.3399 (3) | 0.0522 (11) | |
H34 | 0.5668 | 1.1224 | 0.3464 | 0.063* | |
C35 | 0.3862 (4) | 1.0827 (4) | 0.3065 (3) | 0.0450 (10) | |
H35 | 0.3778 | 1.1443 | 0.2911 | 0.054* | |
C36 | 0.6530 (5) | 0.8812 (5) | 0.4150 (4) | 0.0759 (16) | |
H36A | 0.6078 | 0.8777 | 0.4641 | 0.114* | |
H36B | 0.7380 | 0.8907 | 0.4394 | 0.114* | |
H36C | 0.6282 | 0.8109 | 0.3543 | 0.114* | |
C37 | 0.6634 (10) | 0.2806 (7) | 0.2190 (6) | 0.130 (3) | |
H37 | 0.7136 | 0.3337 | 0.2019 | 0.156* | |
Cl5 | 0.6127 (4) | 0.3611 (2) | 0.3255 (2) | 0.1736 (12) | |
Cl6 | 0.5396 (3) | 0.2068 (4) | 0.1217 (2) | 0.1893 (14) | |
Cl7 | 0.7472 (3) | 0.1841 (3) | 0.2289 (3) | 0.1951 (14) | |
C38 | 0.9830 (18) | 0.4317 (14) | 0.3849 (11) | 0.171 (10) | 0.50 |
H38A | 1.0697 | 0.4500 | 0.4052 | 0.257* | 0.50 |
H38B | 0.9518 | 0.3673 | 0.3964 | 0.257* | 0.50 |
H38C | 0.9485 | 0.4975 | 0.4228 | 0.257* | 0.50 |
O6 | 0.9519 (10) | 0.4021 (10) | 0.2805 (9) | 0.120 (4) | 0.50 |
H6 | 0.9972 | 0.4250 | 0.2488 | 0.144* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0866 (10) | 0.0596 (8) | 0.1011 (11) | 0.0131 (7) | 0.0337 (8) | 0.0434 (8) |
Cl2 | 0.0794 (10) | 0.0859 (10) | 0.0982 (11) | 0.0481 (8) | 0.0356 (8) | 0.0409 (9) |
Cl3 | 0.1083 (12) | 0.0645 (9) | 0.0688 (9) | −0.0088 (8) | 0.0066 (8) | 0.0073 (7) |
Cl4 | 0.0682 (9) | 0.1178 (13) | 0.1119 (13) | 0.0067 (9) | 0.0399 (9) | 0.0557 (11) |
N1 | 0.0428 (19) | 0.0419 (19) | 0.0457 (19) | 0.0044 (15) | 0.0061 (16) | 0.0193 (16) |
N2 | 0.061 (2) | 0.045 (2) | 0.042 (2) | 0.0076 (17) | 0.0098 (16) | 0.0181 (17) |
O1 | 0.0490 (17) | 0.0445 (16) | 0.0578 (19) | 0.0153 (14) | 0.0026 (14) | 0.0202 (14) |
O2 | 0.0339 (14) | 0.0442 (16) | 0.0558 (17) | 0.0065 (12) | 0.0005 (12) | 0.0293 (14) |
O3 | 0.099 (3) | 0.0472 (19) | 0.0476 (19) | −0.0015 (18) | 0.0059 (18) | 0.0089 (15) |
O4 | 0.0665 (19) | 0.0389 (15) | 0.0398 (15) | 0.0035 (13) | 0.0106 (13) | 0.0207 (13) |
O5 | 0.0445 (19) | 0.103 (3) | 0.089 (3) | 0.0165 (18) | 0.0050 (17) | 0.061 (2) |
C1 | 0.040 (2) | 0.040 (2) | 0.0284 (18) | 0.0113 (17) | 0.0082 (15) | 0.0170 (17) |
C2 | 0.035 (2) | 0.036 (2) | 0.039 (2) | 0.0071 (16) | 0.0035 (16) | 0.0164 (17) |
C3 | 0.042 (2) | 0.044 (2) | 0.052 (3) | 0.0105 (18) | 0.0139 (19) | 0.011 (2) |
C4 | 0.038 (2) | 0.058 (3) | 0.049 (2) | 0.0111 (19) | 0.0144 (18) | 0.019 (2) |
C5 | 0.039 (2) | 0.053 (2) | 0.040 (2) | 0.0000 (18) | 0.0071 (17) | 0.0223 (19) |
C6 | 0.043 (2) | 0.036 (2) | 0.037 (2) | 0.0002 (17) | 0.0025 (17) | 0.0197 (17) |
C7 | 0.0316 (19) | 0.037 (2) | 0.041 (2) | 0.0079 (16) | 0.0065 (16) | 0.0155 (17) |
C8 | 0.038 (2) | 0.039 (2) | 0.040 (2) | 0.0111 (17) | 0.0068 (17) | 0.0146 (17) |
C9 | 0.041 (2) | 0.055 (3) | 0.035 (2) | 0.0069 (19) | 0.0104 (17) | 0.0117 (19) |
C10 | 0.056 (3) | 0.066 (3) | 0.043 (2) | −0.005 (2) | 0.012 (2) | 0.018 (2) |
C11 | 0.069 (4) | 0.090 (4) | 0.065 (3) | −0.012 (3) | 0.021 (3) | 0.027 (3) |
C12 | 0.053 (3) | 0.127 (6) | 0.066 (4) | −0.007 (4) | 0.022 (3) | 0.030 (4) |
C13 | 0.044 (3) | 0.131 (6) | 0.057 (3) | 0.024 (3) | 0.017 (2) | 0.029 (3) |
C14 | 0.045 (3) | 0.079 (3) | 0.045 (3) | 0.017 (2) | 0.014 (2) | 0.019 (2) |
C15 | 0.0309 (19) | 0.039 (2) | 0.041 (2) | 0.0033 (16) | 0.0062 (16) | 0.0179 (17) |
C16 | 0.053 (3) | 0.043 (2) | 0.047 (2) | 0.0054 (19) | 0.005 (2) | 0.025 (2) |
C17 | 0.065 (3) | 0.052 (3) | 0.040 (2) | −0.003 (2) | −0.004 (2) | 0.021 (2) |
C18 | 0.059 (3) | 0.037 (2) | 0.041 (2) | −0.0041 (19) | 0.006 (2) | 0.0130 (19) |
C19 | 0.052 (3) | 0.039 (2) | 0.052 (3) | 0.0089 (19) | 0.008 (2) | 0.020 (2) |
C20 | 0.045 (2) | 0.045 (2) | 0.042 (2) | 0.0081 (19) | 0.0006 (18) | 0.019 (2) |
C21 | 0.161 (7) | 0.082 (4) | 0.045 (3) | 0.007 (4) | −0.010 (4) | 0.008 (3) |
C22 | 0.039 (2) | 0.037 (2) | 0.036 (2) | −0.0005 (16) | 0.0047 (16) | 0.0183 (17) |
C23 | 0.045 (2) | 0.044 (2) | 0.039 (2) | 0.0069 (18) | 0.0090 (18) | 0.0197 (19) |
C24 | 0.071 (3) | 0.052 (3) | 0.045 (2) | 0.027 (2) | 0.019 (2) | 0.024 (2) |
C25 | 0.104 (4) | 0.058 (3) | 0.042 (3) | 0.032 (3) | 0.013 (3) | 0.016 (2) |
C26 | 0.146 (6) | 0.081 (4) | 0.046 (3) | 0.039 (4) | 0.022 (4) | 0.020 (3) |
C27 | 0.177 (8) | 0.117 (6) | 0.053 (4) | 0.079 (6) | 0.049 (5) | 0.042 (4) |
C28 | 0.126 (6) | 0.110 (5) | 0.084 (5) | 0.062 (5) | 0.067 (4) | 0.061 (4) |
C29 | 0.077 (4) | 0.078 (4) | 0.068 (3) | 0.035 (3) | 0.033 (3) | 0.043 (3) |
C30 | 0.043 (2) | 0.037 (2) | 0.0295 (19) | 0.0026 (17) | 0.0056 (16) | 0.0144 (16) |
C31 | 0.044 (2) | 0.039 (2) | 0.042 (2) | 0.0017 (17) | 0.0086 (17) | 0.0199 (18) |
C32 | 0.056 (3) | 0.051 (3) | 0.052 (3) | 0.017 (2) | 0.013 (2) | 0.031 (2) |
C33 | 0.043 (2) | 0.067 (3) | 0.042 (2) | 0.011 (2) | 0.0090 (19) | 0.025 (2) |
C34 | 0.042 (2) | 0.059 (3) | 0.053 (3) | −0.007 (2) | 0.0043 (19) | 0.027 (2) |
C35 | 0.049 (2) | 0.042 (2) | 0.047 (2) | 0.0012 (18) | 0.0069 (19) | 0.0241 (19) |
C36 | 0.060 (3) | 0.100 (4) | 0.079 (4) | 0.027 (3) | 0.006 (3) | 0.049 (3) |
C37 | 0.191 (9) | 0.093 (5) | 0.109 (6) | 0.006 (6) | 0.048 (6) | 0.047 (5) |
Cl5 | 0.259 (4) | 0.1184 (19) | 0.137 (2) | 0.048 (2) | 0.080 (2) | 0.0351 (16) |
Cl6 | 0.145 (2) | 0.254 (4) | 0.131 (2) | 0.001 (2) | 0.0345 (18) | 0.055 (2) |
Cl7 | 0.186 (3) | 0.184 (3) | 0.252 (4) | 0.077 (3) | 0.079 (3) | 0.110 (3) |
C38 | 0.133 (16) | 0.078 (11) | 0.28 (3) | 0.045 (11) | −0.005 (17) | 0.067 (15) |
O6 | 0.108 (8) | 0.135 (9) | 0.110 (8) | −0.019 (6) | 0.030 (6) | 0.054 (7) |
Cl1—C10 | 1.734 (6) | C16—H16 | 0.9300 |
Cl2—C14 | 1.721 (6) | C17—C18 | 1.376 (6) |
Cl3—C25 | 1.738 (6) | C17—H17 | 0.9300 |
Cl4—C29 | 1.738 (6) | C18—C19 | 1.368 (6) |
N1—C8 | 1.269 (5) | C19—C20 | 1.384 (6) |
N1—O2 | 1.416 (4) | C19—H19 | 0.9300 |
N2—C23 | 1.267 (5) | C20—H20 | 0.9300 |
N2—O4 | 1.412 (4) | C21—H21A | 0.9600 |
O1—C1 | 1.193 (4) | C21—H21B | 0.9600 |
O2—C2 | 1.469 (4) | C21—H21C | 0.9600 |
O3—C18 | 1.374 (5) | C22—C30 | 1.508 (5) |
O3—C21 | 1.415 (7) | C22—C23 | 1.512 (6) |
O4—C6 | 1.450 (5) | C22—H22 | 0.9800 |
O5—C33 | 1.357 (5) | C23—C24 | 1.482 (6) |
O5—C36 | 1.410 (7) | C24—C29 | 1.391 (7) |
C1—C2 | 1.542 (5) | C24—C25 | 1.399 (7) |
C1—C6 | 1.545 (5) | C25—C26 | 1.385 (7) |
C2—C3 | 1.527 (5) | C26—C27 | 1.358 (11) |
C2—C7 | 1.542 (5) | C26—H26 | 0.9300 |
C3—C4 | 1.521 (6) | C27—C28 | 1.378 (11) |
C3—H3A | 0.9700 | C27—H27 | 0.9300 |
C3—H3B | 0.9700 | C28—C29 | 1.388 (8) |
C4—C5 | 1.503 (6) | C28—H28 | 0.9300 |
C4—H4A | 0.9700 | C30—C31 | 1.378 (5) |
C4—H4B | 0.9700 | C30—C35 | 1.398 (5) |
C5—C6 | 1.529 (6) | C31—C32 | 1.390 (6) |
C5—H5A | 0.9700 | C31—H31 | 0.9300 |
C5—H5B | 0.9700 | C32—C33 | 1.380 (6) |
C6—C22 | 1.561 (5) | C32—H32 | 0.9300 |
C7—C15 | 1.508 (5) | C33—C34 | 1.386 (6) |
C7—C8 | 1.513 (5) | C34—C35 | 1.369 (6) |
C7—H7 | 0.9800 | C34—H34 | 0.9300 |
C8—C9 | 1.482 (6) | C35—H35 | 0.9300 |
C9—C10 | 1.391 (7) | C36—H36A | 0.9600 |
C9—C14 | 1.405 (6) | C36—H36B | 0.9600 |
C10—C11 | 1.388 (7) | C36—H36C | 0.9600 |
C11—C12 | 1.357 (9) | C37—Cl7 | 1.693 (10) |
C11—H11 | 0.9300 | C37—Cl5 | 1.710 (9) |
C12—C13 | 1.379 (9) | C37—Cl6 | 1.742 (10) |
C12—H12 | 0.9300 | C37—H37 | 0.9800 |
C13—C14 | 1.387 (7) | C38—O6 | 1.435 (10) |
C13—H13 | 0.9300 | C38—H38A | 0.9600 |
C15—C16 | 1.371 (5) | C38—H38B | 0.9600 |
C15—C20 | 1.393 (6) | C38—H38C | 0.9600 |
C16—C17 | 1.392 (6) | O6—H6 | 0.8499 |
C8—N1—O2 | 109.4 (3) | O3—C18—C17 | 124.9 (4) |
C23—N2—O4 | 108.9 (3) | C18—C19—C20 | 120.1 (4) |
N1—O2—C2 | 108.5 (3) | C18—C19—H19 | 119.9 |
C18—O3—C21 | 118.6 (4) | C20—C19—H19 | 119.9 |
N2—O4—C6 | 109.1 (3) | C19—C20—C15 | 121.1 (4) |
C33—O5—C36 | 118.0 (4) | C19—C20—H20 | 119.5 |
O1—C1—C2 | 122.3 (3) | C15—C20—H20 | 119.5 |
O1—C1—C6 | 121.1 (3) | O3—C21—H21A | 109.5 |
C2—C1—C6 | 116.5 (3) | O3—C21—H21B | 109.5 |
O2—C2—C3 | 107.1 (3) | H21A—C21—H21B | 109.5 |
O2—C2—C1 | 106.3 (3) | O3—C21—H21C | 109.5 |
C3—C2—C1 | 108.1 (3) | H21A—C21—H21C | 109.5 |
O2—C2—C7 | 103.9 (3) | H21B—C21—H21C | 109.5 |
C3—C2—C7 | 118.4 (3) | C30—C22—C23 | 113.6 (3) |
C1—C2—C7 | 112.2 (3) | C30—C22—C6 | 117.5 (3) |
C4—C3—C2 | 110.2 (3) | C23—C22—C6 | 98.1 (3) |
C4—C3—H3A | 109.6 | C30—C22—H22 | 109.0 |
C2—C3—H3A | 109.6 | C23—C22—H22 | 109.0 |
C4—C3—H3B | 109.6 | C6—C22—H22 | 109.0 |
C2—C3—H3B | 109.6 | N2—C23—C24 | 120.6 (4) |
H3A—C3—H3B | 108.1 | N2—C23—C22 | 115.4 (3) |
C5—C4—C3 | 112.1 (4) | C24—C23—C22 | 124.0 (3) |
C5—C4—H4A | 109.2 | C29—C24—C25 | 116.5 (4) |
C3—C4—H4A | 109.2 | C29—C24—C23 | 120.0 (4) |
C5—C4—H4B | 109.2 | C25—C24—C23 | 123.5 (4) |
C3—C4—H4B | 109.2 | C26—C25—C24 | 122.2 (6) |
H4A—C4—H4B | 107.9 | C26—C25—Cl3 | 117.6 (5) |
C4—C5—C6 | 113.0 (3) | C24—C25—Cl3 | 120.3 (4) |
C4—C5—H5A | 109.0 | C27—C26—C25 | 118.6 (7) |
C6—C5—H5A | 109.0 | C27—C26—H26 | 120.7 |
C4—C5—H5B | 109.0 | C25—C26—H26 | 120.7 |
C6—C5—H5B | 109.0 | C26—C27—C28 | 122.3 (6) |
H5A—C5—H5B | 107.8 | C26—C27—H27 | 118.9 |
O4—C6—C5 | 106.9 (3) | C28—C27—H27 | 118.9 |
O4—C6—C1 | 107.7 (3) | C27—C28—C29 | 118.0 (7) |
C5—C6—C1 | 110.5 (3) | C27—C28—H28 | 121.0 |
O4—C6—C22 | 104.1 (3) | C29—C28—H28 | 121.0 |
C5—C6—C22 | 118.2 (3) | C28—C29—C24 | 122.4 (6) |
C1—C6—C22 | 108.8 (3) | C28—C29—Cl4 | 118.2 (5) |
C15—C7—C8 | 112.5 (3) | C24—C29—Cl4 | 119.3 (4) |
C15—C7—C2 | 116.6 (3) | C31—C30—C35 | 117.9 (4) |
C8—C7—C2 | 99.2 (3) | C31—C30—C22 | 120.2 (3) |
C15—C7—H7 | 109.3 | C35—C30—C22 | 121.9 (3) |
C8—C7—H7 | 109.3 | C30—C31—C32 | 121.6 (4) |
C2—C7—H7 | 109.3 | C30—C31—H31 | 119.2 |
N1—C8—C9 | 119.0 (4) | C32—C31—H31 | 119.2 |
N1—C8—C7 | 114.7 (3) | C33—C32—C31 | 119.7 (4) |
C9—C8—C7 | 126.1 (3) | C33—C32—H32 | 120.1 |
C10—C9—C14 | 116.3 (4) | C31—C32—H32 | 120.1 |
C10—C9—C8 | 123.1 (4) | O5—C33—C32 | 125.5 (4) |
C14—C9—C8 | 120.6 (4) | O5—C33—C34 | 115.4 (4) |
C11—C10—C9 | 122.0 (5) | C32—C33—C34 | 119.1 (4) |
C11—C10—Cl1 | 116.9 (4) | C35—C34—C33 | 120.9 (4) |
C9—C10—Cl1 | 121.1 (4) | C35—C34—H34 | 119.5 |
C12—C11—C10 | 120.1 (6) | C33—C34—H34 | 119.5 |
C12—C11—H11 | 119.9 | C34—C35—C30 | 120.8 (4) |
C10—C11—H11 | 119.9 | C34—C35—H35 | 119.6 |
C11—C12—C13 | 120.3 (5) | C30—C35—H35 | 119.6 |
C11—C12—H12 | 119.8 | O5—C36—H36A | 109.5 |
C13—C12—H12 | 119.8 | O5—C36—H36B | 109.5 |
C12—C13—C14 | 119.6 (6) | H36A—C36—H36B | 109.5 |
C12—C13—H13 | 120.2 | O5—C36—H36C | 109.5 |
C14—C13—H13 | 120.2 | H36A—C36—H36C | 109.5 |
C13—C14—C9 | 121.6 (5) | H36B—C36—H36C | 109.5 |
C13—C14—Cl2 | 118.5 (4) | Cl7—C37—Cl5 | 114.3 (5) |
C9—C14—Cl2 | 119.8 (4) | Cl7—C37—Cl6 | 109.0 (5) |
C16—C15—C20 | 117.7 (4) | Cl5—C37—Cl6 | 109.2 (6) |
C16—C15—C7 | 120.7 (4) | Cl7—C37—H37 | 108.1 |
C20—C15—C7 | 121.6 (3) | Cl5—C37—H37 | 108.1 |
C15—C16—C17 | 121.5 (4) | Cl6—C37—H37 | 108.1 |
C15—C16—H16 | 119.2 | O6—C38—H38A | 109.5 |
C17—C16—H16 | 119.2 | O6—C38—H38B | 109.5 |
C18—C17—C16 | 119.6 (4) | H38A—C38—H38B | 109.5 |
C18—C17—H17 | 120.2 | O6—C38—H38C | 109.5 |
C16—C17—H17 | 120.2 | H38A—C38—H38C | 109.5 |
C19—C18—O3 | 115.2 (4) | H38B—C38—H38C | 109.5 |
C19—C18—C17 | 119.9 (4) | C38—O6—H6 | 124.1 |
C8—N1—O2—C2 | 12.2 (4) | C8—C7—C15—C20 | −51.0 (5) |
C23—N2—O4—C6 | 12.6 (4) | C2—C7—C15—C20 | 62.7 (5) |
N1—O2—C2—C3 | −146.1 (3) | C20—C15—C16—C17 | −2.3 (6) |
N1—O2—C2—C1 | 98.5 (3) | C7—C15—C16—C17 | 176.1 (4) |
N1—O2—C2—C7 | −20.1 (3) | C15—C16—C17—C18 | 1.0 (7) |
O1—C1—C2—O2 | −118.9 (4) | C21—O3—C18—C19 | −175.1 (5) |
C6—C1—C2—O2 | 62.3 (4) | C21—O3—C18—C17 | 4.7 (7) |
O1—C1—C2—C3 | 126.4 (4) | C16—C17—C18—C19 | 0.7 (7) |
C6—C1—C2—C3 | −52.3 (4) | C16—C17—C18—O3 | −179.2 (4) |
O1—C1—C2—C7 | −5.9 (5) | O3—C18—C19—C20 | 179.0 (4) |
C6—C1—C2—C7 | 175.3 (3) | C17—C18—C19—C20 | −0.9 (7) |
O2—C2—C3—C4 | −56.9 (4) | C18—C19—C20—C15 | −0.5 (6) |
C1—C2—C3—C4 | 57.3 (4) | C16—C15—C20—C19 | 2.1 (6) |
C7—C2—C3—C4 | −173.8 (3) | C7—C15—C20—C19 | −176.3 (4) |
C2—C3—C4—C5 | −61.6 (5) | O4—C6—C22—C30 | −103.2 (4) |
C3—C4—C5—C6 | 56.1 (5) | C5—C6—C22—C30 | 15.2 (5) |
N2—O4—C6—C5 | −146.0 (3) | C1—C6—C22—C30 | 142.2 (3) |
N2—O4—C6—C1 | 95.2 (3) | O4—C6—C22—C23 | 18.8 (4) |
N2—O4—C6—C22 | −20.2 (4) | C5—C6—C22—C23 | 137.2 (3) |
C4—C5—C6—O4 | −164.0 (3) | C1—C6—C22—C23 | −95.8 (3) |
C4—C5—C6—C1 | −47.1 (4) | O4—N2—C23—C24 | −179.9 (4) |
C4—C5—C6—C22 | 79.2 (4) | O4—N2—C23—C22 | 1.4 (5) |
O1—C1—C6—O4 | −15.3 (5) | C30—C22—C23—N2 | 111.7 (4) |
C2—C1—C6—O4 | 163.5 (3) | C6—C22—C23—N2 | −13.1 (4) |
O1—C1—C6—C5 | −131.8 (4) | C30—C22—C23—C24 | −67.0 (5) |
C2—C1—C6—C5 | 47.0 (4) | C6—C22—C23—C24 | 168.1 (4) |
O1—C1—C6—C22 | 97.0 (4) | N2—C23—C24—C29 | 113.7 (5) |
C2—C1—C6—C22 | −84.3 (4) | C22—C23—C24—C29 | −67.6 (6) |
O2—C2—C7—C15 | −102.0 (3) | N2—C23—C24—C25 | −65.9 (6) |
C3—C2—C7—C15 | 16.5 (5) | C22—C23—C24—C25 | 112.8 (5) |
C1—C2—C7—C15 | 143.6 (3) | C29—C24—C25—C26 | 0.8 (7) |
O2—C2—C7—C8 | 19.0 (3) | C23—C24—C25—C26 | −179.7 (5) |
C3—C2—C7—C8 | 137.6 (3) | C29—C24—C25—Cl3 | −179.9 (4) |
C1—C2—C7—C8 | −95.4 (3) | C23—C24—C25—Cl3 | −0.3 (6) |
O2—N1—C8—C9 | 176.4 (3) | C24—C25—C26—C27 | 0.4 (9) |
O2—N1—C8—C7 | 1.6 (4) | Cl3—C25—C26—C27 | −179.1 (5) |
C15—C7—C8—N1 | 110.4 (4) | C25—C26—C27—C28 | −1.6 (10) |
C2—C7—C8—N1 | −13.6 (4) | C26—C27—C28—C29 | 1.7 (10) |
C15—C7—C8—C9 | −63.9 (5) | C27—C28—C29—C24 | −0.5 (9) |
C2—C7—C8—C9 | 172.1 (4) | C27—C28—C29—Cl4 | −177.3 (5) |
N1—C8—C9—C10 | −56.7 (6) | C25—C24—C29—C28 | −0.7 (7) |
C7—C8—C9—C10 | 117.4 (5) | C23—C24—C29—C28 | 179.7 (5) |
N1—C8—C9—C14 | 122.8 (4) | C25—C24—C29—Cl4 | 176.1 (4) |
C7—C8—C9—C14 | −63.1 (5) | C23—C24—C29—Cl4 | −3.5 (6) |
C14—C9—C10—C11 | 1.5 (7) | C23—C22—C30—C31 | 130.6 (4) |
C8—C9—C10—C11 | −179.0 (4) | C6—C22—C30—C31 | −115.8 (4) |
C14—C9—C10—Cl1 | −178.9 (3) | C23—C22—C30—C35 | −50.9 (5) |
C8—C9—C10—Cl1 | 0.6 (6) | C6—C22—C30—C35 | 62.7 (5) |
C9—C10—C11—C12 | 0.2 (8) | C35—C30—C31—C32 | −0.6 (6) |
Cl1—C10—C11—C12 | −179.4 (4) | C22—C30—C31—C32 | 178.0 (4) |
C10—C11—C12—C13 | −1.5 (9) | C30—C31—C32—C33 | 0.7 (6) |
C11—C12—C13—C14 | 1.1 (9) | C36—O5—C33—C32 | 3.8 (7) |
C12—C13—C14—C9 | 0.7 (8) | C36—O5—C33—C34 | −175.4 (4) |
C12—C13—C14—Cl2 | −176.5 (4) | C31—C32—C33—O5 | −179.9 (4) |
C10—C9—C14—C13 | −1.9 (6) | C31—C32—C33—C34 | −0.6 (6) |
C8—C9—C14—C13 | 178.6 (4) | O5—C33—C34—C35 | 179.9 (4) |
C10—C9—C14—Cl2 | 175.3 (3) | C32—C33—C34—C35 | 0.6 (7) |
C8—C9—C14—Cl2 | −4.2 (6) | C33—C34—C35—C30 | −0.5 (7) |
C8—C7—C15—C16 | 130.7 (4) | C31—C30—C35—C34 | 0.5 (6) |
C2—C7—C15—C16 | −115.6 (4) | C22—C30—C35—C34 | −178.0 (4) |