In the title compound, C
22H
26F
3N
2O
3PS, there are two independent molecules in the asymmetric unit. The two molecules differ in the orientation of the benzene ring with respect to the benzothiazole group [dihedral angles 58.6 (2) and 71.6 (2)°]. In the crystal structure, symmetry-related molecules are linked by N—H
O hydrogen bonds.
Supporting information
CCDC reference: 274357
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.011 Å
- R factor = 0.062
- wR factor = 0.228
- Data-to-parameter ratio = 15.6
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 33 Perc.
PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.07 Ratio
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.73 Ratio
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.07 Ratio
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C20
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C17'
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C39
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C42
PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 11
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.46 Ratio
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S1
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C3
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C12
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C26
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C34
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C16
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C35
PLAT301_ALERT_3_C Main Residue Disorder ......................... 12.00 Perc.
PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ?
PLAT322_ALERT_2_C Check Hybridisation of S2 in Main Residue . ?
0 ALERT level A = In general: serious problem
9 ALERT level B = Potentially serious problem
15 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
19 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
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.
Diisopropyl
{(4-methylbenzothiazol-2-ylamino)[4-(trifluoromethyl)phenyl]methyl}phosphonate
top
Crystal data top
C22H26F3N2O3PS | F(000) = 2032 |
Mr = 486.49 | Dx = 1.280 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3118 reflections |
a = 13.819 (2) Å | θ = 2.3–19.3° |
b = 21.354 (3) Å | µ = 0.24 mm−1 |
c = 21.991 (3) Å | T = 293 K |
β = 128.931 (6)° | Prism, colourless |
V = 5048.1 (12) Å3 | 0.30 × 0.26 × 0.22 mm |
Z = 8 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 10401 independent reflections |
Radiation source: fine-focus sealed tube | 3429 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.083 |
φ and ω scans | θmax = 26.5°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −15→17 |
Tmin = 0.918, Tmax = 0.949 | k = −23→26 |
29353 measured reflections | l = −27→27 |
Refinement top
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)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.228 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.93 | w = 1/[σ2(Fo2) + (0.1048P)2] where P = (Fo2 + 2Fc2)/3 |
10401 reflections | (Δ/σ)max = 0.003 |
667 parameters | Δρmax = 0.34 e Å−3 |
186 restraints | Δρmin = −0.26 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
P1 | 0.26354 (13) | 0.81905 (7) | 0.16031 (8) | 0.0689 (4) | |
P2 | 0.56179 (12) | 0.82014 (7) | 0.67057 (8) | 0.0686 (4) | |
S1 | 0.73905 (13) | 0.83127 (8) | 0.36680 (9) | 0.0931 (5) | |
S2 | 0.08986 (13) | 0.80018 (7) | 0.43290 (8) | 0.0835 (5) | |
F1 | 0.152 (2) | 0.5507 (9) | 0.2761 (7) | 0.209 (9) | 0.416 (16) |
F2 | 0.1695 (16) | 0.5989 (6) | 0.3696 (11) | 0.156 (6) | 0.416 (16) |
F3 | 0.3217 (11) | 0.5483 (8) | 0.3932 (11) | 0.152 (6) | 0.416 (16) |
F1' | 0.1057 (6) | 0.5729 (5) | 0.2867 (7) | 0.143 (4) | 0.584 (16) |
F2' | 0.2547 (18) | 0.5879 (7) | 0.4092 (7) | 0.210 (6) | 0.584 (16) |
F3' | 0.2806 (11) | 0.5314 (4) | 0.3408 (10) | 0.166 (5) | 0.584 (16) |
F4 | 0.5606 (10) | 0.5567 (4) | 0.4498 (9) | 0.170 (5) | 0.689 (19) |
F5 | 0.6571 (11) | 0.6225 (5) | 0.4317 (6) | 0.145 (4) | 0.689 (19) |
F6 | 0.7501 (9) | 0.5787 (6) | 0.5424 (4) | 0.146 (4) | 0.689 (19) |
F4' | 0.598 (2) | 0.5970 (11) | 0.4121 (6) | 0.146 (8) | 0.311 (19) |
F5' | 0.7695 (10) | 0.6069 (11) | 0.5286 (12) | 0.131 (8) | 0.311 (19) |
F6' | 0.628 (3) | 0.5469 (6) | 0.5066 (16) | 0.150 (8) | 0.311 (19) |
O1 | 0.2726 (3) | 0.77682 (16) | 0.11200 (18) | 0.0803 (10) | |
O3 | 0.1367 (3) | 0.81859 (17) | 0.1434 (2) | 0.0826 (10) | |
O4 | 0.5828 (3) | 0.76527 (17) | 0.71781 (18) | 0.0911 (11) | |
O5 | 0.6809 (3) | 0.84813 (16) | 0.68845 (18) | 0.0759 (10) | |
O6 | 0.4958 (3) | 0.87014 (19) | 0.6825 (2) | 0.0934 (11) | |
N1 | 0.5914 (4) | 0.86479 (17) | 0.3963 (2) | 0.0611 (10) | |
N2 | 0.4986 (4) | 0.8015 (2) | 0.2849 (2) | 0.0718 (13) | |
H2A | 0.516 (4) | 0.780 (2) | 0.259 (3) | 0.086* | |
N3 | 0.2502 (3) | 0.85380 (17) | 0.4246 (2) | 0.0579 (10) | |
N4 | 0.3383 (4) | 0.7931 (2) | 0.5366 (2) | 0.0699 (12) | |
H4A | 0.328 (4) | 0.767 (2) | 0.564 (3) | 0.084* | |
C1 | 0.7981 (5) | 0.8789 (3) | 0.4468 (3) | 0.0818 (16) | |
C2 | 0.9177 (6) | 0.9034 (4) | 0.4990 (4) | 0.124 (2) | |
H2 | 0.9783 | 0.8953 | 0.4938 | 0.148* | |
C3 | 0.9423 (7) | 0.9403 (4) | 0.5586 (4) | 0.135 (3) | |
H3 | 1.0220 | 0.9563 | 0.5954 | 0.162* | |
C4 | 0.8524 (7) | 0.9539 (3) | 0.5649 (4) | 0.112 (2) | |
H4 | 0.8718 | 0.9801 | 0.6050 | 0.135* | |
C5 | 0.7330 (6) | 0.9299 (3) | 0.5132 (3) | 0.0834 (16) | |
C6 | 0.7066 (5) | 0.8913 (2) | 0.4531 (3) | 0.0687 (14) | |
C7 | 0.6353 (6) | 0.9460 (3) | 0.5209 (4) | 0.113 (2) | |
H7A | 0.6565 | 0.9272 | 0.5675 | 0.170* | |
H7B | 0.5562 | 0.9304 | 0.4763 | 0.170* | |
H7C | 0.6310 | 0.9906 | 0.5238 | 0.170* | |
C8 | 0.5954 (4) | 0.8323 (2) | 0.3478 (3) | 0.0576 (12) | |
C9 | 0.3757 (4) | 0.8036 (2) | 0.2636 (3) | 0.0620 (13) | |
H9 | 0.3740 | 0.8391 | 0.2911 | 0.074* | |
C10 | 0.3420 (4) | 0.7457 (2) | 0.2859 (2) | 0.0581 (12) | |
C11 | 0.3547 (6) | 0.6872 (3) | 0.2668 (3) | 0.0892 (17) | |
H11 | 0.3892 | 0.6827 | 0.2418 | 0.107* | |
C12 | 0.3174 (6) | 0.6347 (3) | 0.2837 (4) | 0.110 (2) | |
H12 | 0.3257 | 0.5951 | 0.2698 | 0.132* | |
C13 | 0.2676 (6) | 0.6414 (3) | 0.3216 (4) | 0.0932 (18) | |
C14 | 0.2562 (5) | 0.6993 (3) | 0.3417 (3) | 0.0855 (17) | |
H14 | 0.2234 | 0.7039 | 0.3676 | 0.103* | |
C15 | 0.2930 (4) | 0.7510 (3) | 0.3240 (3) | 0.0721 (14) | |
H15 | 0.2845 | 0.7904 | 0.3380 | 0.087* | |
C16 | 0.2282 (7) | 0.5858 (4) | 0.3398 (4) | 0.138 (3) | |
O2 | 0.2879 (4) | 0.88942 (17) | 0.1558 (2) | 0.1036 (13) | |
C17 | 0.2958 (14) | 0.9127 (7) | 0.0967 (7) | 0.127 (5) | 0.538 (13) |
H17A | 0.2772 | 0.8789 | 0.0606 | 0.152* | 0.538 (13) |
C18 | 0.4263 (14) | 0.9380 (6) | 0.1370 (9) | 0.138 (6) | 0.538 (13) |
H18A | 0.4866 | 0.9075 | 0.1734 | 0.206* | 0.538 (13) |
H18B | 0.4379 | 0.9759 | 0.1644 | 0.206* | 0.538 (13) |
H18C | 0.4367 | 0.9467 | 0.0985 | 0.206* | 0.538 (13) |
C19 | 0.196 (2) | 0.9629 (10) | 0.0539 (14) | 0.212 (10) | 0.538 (13) |
H19A | 0.1193 | 0.9468 | 0.0402 | 0.318* | 0.538 (13) |
H19B | 0.1828 | 0.9750 | 0.0073 | 0.318* | 0.538 (13) |
H19C | 0.2212 | 0.9988 | 0.0872 | 0.318* | 0.538 (13) |
C17' | 0.2025 (15) | 0.9199 (9) | 0.0781 (8) | 0.137 (7) | 0.462 (13) |
H17B | 0.1393 | 0.8903 | 0.0389 | 0.164* | 0.462 (13) |
C18' | 0.284 (3) | 0.9417 (14) | 0.0577 (18) | 0.212 (12) | 0.462 (13) |
H18D | 0.3541 | 0.9140 | 0.0813 | 0.317* | 0.462 (13) |
H18E | 0.3133 | 0.9834 | 0.0770 | 0.317* | 0.462 (13) |
H18F | 0.2367 | 0.9413 | 0.0020 | 0.317* | 0.462 (13) |
C19' | 0.144 (3) | 0.9769 (13) | 0.0795 (14) | 0.234 (13) | 0.462 (13) |
H19D | 0.0915 | 0.9660 | 0.0926 | 0.350* | 0.462 (13) |
H19E | 0.0946 | 0.9964 | 0.0289 | 0.350* | 0.462 (13) |
H19F | 0.2072 | 1.0055 | 0.1178 | 0.350* | 0.462 (13) |
C20 | 0.0349 (6) | 0.7764 (4) | 0.0878 (4) | 0.113 (2) | |
H20 | 0.0700 | 0.7395 | 0.0814 | 0.135* | |
C21 | −0.0224 (6) | 0.7559 (4) | 0.1235 (4) | 0.159 (3) | |
H21A | 0.0353 | 0.7299 | 0.1681 | 0.239* | |
H21B | −0.0968 | 0.7325 | 0.0859 | 0.239* | |
H21C | −0.0426 | 0.7919 | 0.1397 | 0.239* | |
C22 | −0.0508 (8) | 0.8076 (5) | 0.0111 (5) | 0.201 (5) | |
H22A | −0.0766 | 0.8471 | 0.0175 | 0.302* | |
H22B | −0.1224 | 0.7815 | −0.0236 | 0.302* | |
H22C | −0.0092 | 0.8144 | −0.0105 | 0.302* | |
C23 | 0.1322 (5) | 0.8713 (2) | 0.3573 (3) | 0.0598 (12) | |
C24 | 0.1103 (5) | 0.9091 (2) | 0.2982 (3) | 0.0700 (14) | |
C25 | −0.0138 (6) | 0.9211 (3) | 0.2356 (3) | 0.0950 (19) | |
H25 | −0.0316 | 0.9473 | 0.1959 | 0.114* | |
C26 | −0.1111 (6) | 0.8964 (4) | 0.2294 (4) | 0.122 (2) | |
H26 | −0.1924 | 0.9047 | 0.1853 | 0.146* | |
C27 | −0.0894 (6) | 0.8596 (4) | 0.2873 (4) | 0.112 (2) | |
H27 | −0.1551 | 0.8438 | 0.2843 | 0.135* | |
C28 | 0.0330 (5) | 0.8463 (3) | 0.3512 (3) | 0.0784 (15) | |
C29 | 0.2409 (4) | 0.8177 (2) | 0.4680 (3) | 0.0574 (12) | |
C30 | 0.2146 (5) | 0.9355 (2) | 0.3023 (3) | 0.0827 (16) | |
H30A | 0.2022 | 0.9251 | 0.2554 | 0.124* | |
H30B | 0.2920 | 0.9181 | 0.3466 | 0.124* | |
H30C | 0.2164 | 0.9802 | 0.3076 | 0.124* | |
C31 | 0.4652 (4) | 0.8043 (2) | 0.5669 (2) | 0.0610 (13) | |
H31 | 0.4644 | 0.8423 | 0.5416 | 0.073* | |
C32 | 0.5171 (4) | 0.7520 (2) | 0.5481 (3) | 0.0613 (12) | |
C33 | 0.5114 (6) | 0.6915 (3) | 0.5651 (3) | 0.0901 (17) | |
H33 | 0.4797 | 0.6826 | 0.5910 | 0.108* | |
C34 | 0.5518 (6) | 0.6430 (3) | 0.5446 (4) | 0.106 (2) | |
H34 | 0.5463 | 0.6019 | 0.5562 | 0.127* | |
C35 | 0.5995 (6) | 0.6550 (3) | 0.5077 (4) | 0.0910 (18) | |
C36 | 0.6091 (5) | 0.7156 (4) | 0.4912 (3) | 0.0876 (17) | |
H36 | 0.6437 | 0.7240 | 0.4670 | 0.105* | |
C37 | 0.5667 (4) | 0.7645 (3) | 0.5110 (3) | 0.0719 (14) | |
H37 | 0.5717 | 0.8055 | 0.4991 | 0.086* | |
C38 | 0.6428 (7) | 0.6040 (4) | 0.4854 (4) | 0.129 (3) | |
C39 | 0.8070 (6) | 0.8271 (3) | 0.7531 (4) | 0.1015 (19) | |
H39 | 0.8005 | 0.7877 | 0.7732 | 0.122* | |
C40 | 0.8664 (8) | 0.8729 (5) | 0.8154 (5) | 0.180 (4) | |
H40A | 0.8777 | 0.9113 | 0.7977 | 0.270* | |
H40B | 0.9459 | 0.8573 | 0.8597 | 0.270* | |
H40C | 0.8151 | 0.8806 | 0.8301 | 0.270* | |
C41 | 0.8729 (8) | 0.8145 (4) | 0.7222 (5) | 0.180 (4) | |
H41A | 0.8299 | 0.7825 | 0.6829 | 0.270* | |
H41B | 0.9560 | 0.8008 | 0.7638 | 0.270* | |
H41C | 0.8761 | 0.8521 | 0.6995 | 0.270* | |
C42 | 0.4516 (7) | 0.9288 (3) | 0.6437 (4) | 0.112 (2) | |
H42 | 0.4408 | 0.9279 | 0.5953 | 0.134* | |
C43 | 0.5400 (8) | 0.9792 (4) | 0.6964 (6) | 0.198 (4) | |
H43A | 0.6185 | 0.9723 | 0.7078 | 0.297* | 0.50 |
H43B | 0.5514 | 0.9786 | 0.7442 | 0.297* | 0.50 |
H43C | 0.5071 | 1.0191 | 0.6713 | 0.297* | 0.50 |
H43D | 0.4995 | 1.0077 | 0.7078 | 0.297* | 0.50 |
H43E | 0.5667 | 1.0014 | 0.6713 | 0.297* | 0.50 |
H43F | 0.6109 | 0.9610 | 0.7442 | 0.297* | 0.50 |
C44 | 0.3268 (7) | 0.9402 (4) | 0.6260 (5) | 0.149 (3) | |
H44A | 0.2806 | 0.9018 | 0.6094 | 0.223* | |
H44B | 0.2803 | 0.9709 | 0.5852 | 0.223* | |
H44C | 0.3412 | 0.9552 | 0.6722 | 0.223* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0876 (10) | 0.0681 (10) | 0.0719 (9) | 0.0018 (8) | 0.0602 (9) | −0.0047 (8) |
P2 | 0.0706 (9) | 0.0830 (10) | 0.0633 (8) | −0.0014 (8) | 0.0475 (8) | 0.0055 (8) |
S1 | 0.0730 (9) | 0.1239 (13) | 0.0942 (11) | −0.0067 (9) | 0.0582 (9) | −0.0351 (10) |
S2 | 0.0717 (9) | 0.1082 (12) | 0.0846 (10) | 0.0062 (8) | 0.0558 (8) | 0.0186 (9) |
F1 | 0.227 (13) | 0.182 (12) | 0.203 (11) | −0.062 (8) | 0.127 (9) | 0.024 (7) |
F2 | 0.148 (9) | 0.170 (9) | 0.159 (10) | −0.021 (7) | 0.101 (8) | 0.045 (7) |
F3 | 0.157 (9) | 0.128 (9) | 0.154 (9) | 0.008 (6) | 0.089 (7) | 0.060 (7) |
F1' | 0.109 (5) | 0.122 (6) | 0.189 (8) | −0.033 (4) | 0.089 (5) | 0.014 (5) |
F2' | 0.251 (11) | 0.209 (9) | 0.191 (8) | −0.054 (8) | 0.149 (8) | 0.042 (7) |
F3' | 0.167 (8) | 0.104 (6) | 0.190 (9) | −0.012 (5) | 0.095 (7) | 0.039 (6) |
F4 | 0.148 (6) | 0.150 (6) | 0.192 (9) | 0.008 (5) | 0.096 (6) | −0.065 (6) |
F5 | 0.161 (7) | 0.158 (7) | 0.128 (6) | 0.026 (5) | 0.096 (5) | −0.039 (5) |
F6 | 0.139 (6) | 0.146 (7) | 0.123 (5) | 0.075 (5) | 0.067 (4) | 0.011 (4) |
F4' | 0.165 (12) | 0.137 (12) | 0.111 (10) | 0.024 (8) | 0.075 (8) | −0.025 (7) |
F5' | 0.124 (10) | 0.124 (11) | 0.150 (11) | 0.028 (7) | 0.089 (8) | 0.010 (7) |
F6' | 0.171 (12) | 0.125 (11) | 0.157 (12) | 0.027 (8) | 0.104 (9) | −0.010 (7) |
O1 | 0.094 (2) | 0.091 (3) | 0.073 (2) | 0.005 (2) | 0.061 (2) | −0.017 (2) |
O3 | 0.076 (2) | 0.102 (3) | 0.082 (2) | 0.007 (2) | 0.055 (2) | −0.010 (2) |
O4 | 0.100 (3) | 0.110 (3) | 0.066 (2) | −0.016 (2) | 0.053 (2) | 0.023 (2) |
O5 | 0.068 (2) | 0.091 (3) | 0.073 (2) | −0.0028 (19) | 0.047 (2) | 0.0173 (19) |
O6 | 0.106 (3) | 0.097 (3) | 0.099 (3) | 0.013 (2) | 0.076 (3) | 0.005 (2) |
N1 | 0.078 (3) | 0.058 (2) | 0.065 (3) | −0.013 (2) | 0.053 (2) | −0.015 (2) |
N2 | 0.070 (3) | 0.091 (3) | 0.076 (3) | −0.019 (2) | 0.056 (3) | −0.036 (3) |
N3 | 0.066 (3) | 0.061 (3) | 0.056 (2) | 0.011 (2) | 0.043 (2) | 0.009 (2) |
N4 | 0.059 (3) | 0.093 (3) | 0.062 (3) | 0.006 (2) | 0.040 (2) | 0.023 (2) |
C1 | 0.067 (4) | 0.096 (4) | 0.080 (4) | −0.010 (3) | 0.045 (3) | −0.026 (3) |
C2 | 0.082 (5) | 0.163 (7) | 0.127 (6) | −0.023 (5) | 0.066 (5) | −0.052 (5) |
C3 | 0.088 (5) | 0.174 (8) | 0.119 (6) | −0.028 (5) | 0.053 (5) | −0.063 (6) |
C4 | 0.117 (6) | 0.112 (5) | 0.092 (5) | −0.020 (5) | 0.058 (5) | −0.038 (4) |
C5 | 0.095 (5) | 0.083 (4) | 0.079 (4) | −0.014 (3) | 0.058 (4) | −0.020 (3) |
C6 | 0.079 (4) | 0.063 (3) | 0.068 (3) | −0.001 (3) | 0.048 (3) | −0.007 (3) |
C7 | 0.147 (6) | 0.114 (5) | 0.119 (5) | −0.027 (4) | 0.103 (5) | −0.046 (4) |
C8 | 0.070 (3) | 0.058 (3) | 0.064 (3) | −0.002 (3) | 0.052 (3) | −0.004 (3) |
C9 | 0.076 (3) | 0.065 (3) | 0.069 (3) | −0.010 (3) | 0.057 (3) | −0.017 (3) |
C10 | 0.066 (3) | 0.066 (3) | 0.053 (3) | 0.002 (3) | 0.042 (3) | −0.007 (3) |
C11 | 0.128 (5) | 0.077 (4) | 0.093 (4) | 0.004 (4) | 0.084 (4) | −0.006 (4) |
C12 | 0.163 (7) | 0.068 (4) | 0.118 (5) | −0.007 (4) | 0.098 (5) | −0.002 (4) |
C13 | 0.102 (5) | 0.090 (5) | 0.088 (4) | −0.022 (4) | 0.060 (4) | 0.008 (4) |
C14 | 0.081 (4) | 0.112 (5) | 0.079 (4) | −0.011 (4) | 0.058 (3) | 0.002 (4) |
C15 | 0.079 (4) | 0.086 (4) | 0.064 (3) | −0.005 (3) | 0.051 (3) | −0.009 (3) |
C16 | 0.171 (10) | 0.130 (8) | 0.134 (8) | −0.019 (7) | 0.107 (8) | 0.006 (7) |
O2 | 0.169 (4) | 0.072 (3) | 0.109 (3) | −0.005 (3) | 0.107 (3) | 0.007 (2) |
C17 | 0.152 (10) | 0.124 (9) | 0.125 (9) | −0.007 (7) | 0.098 (7) | 0.013 (7) |
C18 | 0.167 (10) | 0.141 (10) | 0.151 (10) | 0.000 (7) | 0.122 (8) | −0.004 (7) |
C19 | 0.209 (13) | 0.213 (14) | 0.217 (13) | 0.002 (9) | 0.136 (10) | 0.055 (9) |
C17' | 0.147 (11) | 0.124 (11) | 0.141 (11) | −0.014 (8) | 0.091 (8) | 0.006 (8) |
C18' | 0.236 (15) | 0.219 (16) | 0.211 (15) | −0.005 (9) | 0.156 (11) | 0.030 (9) |
C19' | 0.248 (15) | 0.227 (15) | 0.223 (15) | 0.034 (10) | 0.147 (11) | 0.022 (9) |
C20 | 0.088 (5) | 0.150 (6) | 0.112 (5) | −0.006 (5) | 0.069 (5) | −0.018 (5) |
C21 | 0.104 (5) | 0.233 (10) | 0.132 (6) | −0.037 (6) | 0.070 (5) | 0.001 (6) |
C22 | 0.115 (7) | 0.332 (14) | 0.098 (6) | −0.009 (8) | 0.039 (5) | 0.009 (8) |
C23 | 0.064 (3) | 0.065 (3) | 0.053 (3) | 0.013 (3) | 0.038 (3) | 0.004 (3) |
C24 | 0.092 (4) | 0.065 (3) | 0.060 (3) | 0.016 (3) | 0.052 (3) | 0.006 (3) |
C25 | 0.099 (5) | 0.103 (5) | 0.066 (4) | 0.033 (4) | 0.043 (4) | 0.029 (3) |
C26 | 0.080 (5) | 0.171 (7) | 0.100 (5) | 0.039 (5) | 0.049 (4) | 0.049 (5) |
C27 | 0.069 (4) | 0.158 (7) | 0.104 (5) | 0.012 (4) | 0.051 (4) | 0.024 (5) |
C28 | 0.074 (4) | 0.096 (4) | 0.072 (4) | 0.015 (3) | 0.048 (3) | 0.014 (3) |
C29 | 0.066 (3) | 0.064 (3) | 0.057 (3) | 0.008 (3) | 0.046 (3) | 0.005 (3) |
C30 | 0.114 (5) | 0.073 (4) | 0.080 (4) | 0.005 (3) | 0.070 (4) | 0.010 (3) |
C31 | 0.065 (3) | 0.067 (3) | 0.060 (3) | 0.003 (3) | 0.044 (3) | 0.014 (3) |
C32 | 0.064 (3) | 0.071 (4) | 0.049 (3) | 0.002 (3) | 0.036 (3) | 0.006 (3) |
C33 | 0.117 (5) | 0.078 (4) | 0.105 (5) | 0.014 (4) | 0.084 (4) | 0.014 (4) |
C34 | 0.136 (6) | 0.076 (4) | 0.132 (6) | 0.009 (4) | 0.097 (5) | 0.015 (4) |
C35 | 0.087 (4) | 0.086 (5) | 0.081 (4) | 0.022 (4) | 0.044 (4) | −0.001 (4) |
C36 | 0.075 (4) | 0.125 (6) | 0.070 (4) | 0.011 (4) | 0.049 (3) | −0.008 (4) |
C37 | 0.076 (3) | 0.081 (4) | 0.064 (3) | −0.002 (3) | 0.047 (3) | 0.002 (3) |
C38 | 0.128 (7) | 0.122 (7) | 0.133 (8) | 0.030 (6) | 0.080 (7) | −0.007 (6) |
C39 | 0.082 (4) | 0.109 (5) | 0.119 (5) | 0.001 (4) | 0.066 (4) | 0.010 (4) |
C40 | 0.159 (6) | 0.208 (7) | 0.122 (5) | 0.010 (6) | 0.064 (5) | −0.032 (6) |
C41 | 0.133 (6) | 0.236 (8) | 0.183 (7) | 0.011 (5) | 0.106 (5) | −0.017 (6) |
C42 | 0.146 (6) | 0.078 (5) | 0.138 (6) | −0.002 (5) | 0.102 (5) | 0.021 (5) |
C43 | 0.164 (7) | 0.127 (6) | 0.231 (8) | −0.016 (5) | 0.090 (6) | −0.002 (6) |
C44 | 0.137 (5) | 0.139 (6) | 0.200 (7) | 0.026 (5) | 0.120 (5) | 0.034 (5) |
Geometric parameters (Å, º) top
P1—O1 | 1.458 (3) | C18—H18C | 0.96 |
P1—O3 | 1.547 (4) | C19—H19A | 0.96 |
P1—O2 | 1.556 (4) | C19—H19B | 0.96 |
P1—C9 | 1.802 (5) | C19—H19C | 0.96 |
P2—O4 | 1.469 (3) | C17'—C19' | 1.47 (3) |
P2—O6 | 1.530 (4) | C17'—C18' | 1.526 (7) |
P2—O5 | 1.552 (3) | C17'—H17B | 0.98 |
P2—C31 | 1.808 (4) | C18'—H18D | 0.96 |
S1—C1 | 1.730 (5) | C18'—H18E | 0.96 |
S1—C8 | 1.753 (5) | C18'—H18F | 0.96 |
S2—C28 | 1.745 (5) | C19'—H19D | 0.96 |
S2—C29 | 1.751 (5) | C19'—H19E | 0.96 |
F1—C16 | 1.333 (9) | C19'—H19F | 0.96 |
F2—C16 | 1.356 (9) | C20—C22 | 1.476 (9) |
F3—C16 | 1.336 (9) | C20—C21 | 1.491 (8) |
F1'—C16 | 1.349 (8) | C20—H20 | 0.98 |
F2'—C16 | 1.329 (8) | C21—H21A | 0.96 |
F3'—C16 | 1.362 (8) | C21—H21B | 0.96 |
F4—C38 | 1.345 (8) | C21—H21C | 0.96 |
F5—C38 | 1.374 (8) | C22—H22A | 0.96 |
F6—C38 | 1.314 (7) | C22—H22B | 0.96 |
F4'—C38 | 1.324 (9) | C22—H22C | 0.96 |
F5'—C38 | 1.372 (9) | C23—C24 | 1.393 (6) |
F6'—C38 | 1.366 (9) | C23—C28 | 1.395 (7) |
O3—C20 | 1.458 (7) | C24—C25 | 1.391 (7) |
O5—C39 | 1.464 (6) | C24—C30 | 1.497 (7) |
O6—C42 | 1.419 (6) | C25—C26 | 1.370 (8) |
N1—C8 | 1.303 (5) | C25—H25 | 0.93 |
N1—C6 | 1.384 (6) | C26—C27 | 1.360 (8) |
N2—C8 | 1.344 (6) | C26—H26 | 0.93 |
N2—C9 | 1.451 (6) | C27—C28 | 1.389 (7) |
N2—H2A | 0.87 (5) | C27—H27 | 0.93 |
N3—C29 | 1.295 (5) | C30—H30A | 0.96 |
N3—C23 | 1.398 (5) | C30—H30B | 0.96 |
N4—C29 | 1.346 (6) | C30—H30C | 0.96 |
N4—C31 | 1.453 (6) | C31—C32 | 1.517 (6) |
N4—H4A | 0.90 (5) | C31—H31 | 0.98 |
C1—C6 | 1.381 (7) | C32—C33 | 1.362 (7) |
C1—C2 | 1.392 (7) | C32—C37 | 1.383 (6) |
C2—C3 | 1.376 (8) | C33—C34 | 1.379 (8) |
C2—H2 | 0.93 | C33—H33 | 0.93 |
C3—C4 | 1.365 (8) | C34—C35 | 1.354 (8) |
C3—H3 | 0.93 | C34—H34 | 0.93 |
C4—C5 | 1.386 (8) | C35—C36 | 1.372 (8) |
C4—H4 | 0.93 | C35—C38 | 1.467 (9) |
C5—C6 | 1.398 (7) | C36—C37 | 1.392 (7) |
C5—C7 | 1.501 (7) | C36—H36 | 0.93 |
C7—H7A | 0.96 | C37—H37 | 0.93 |
C7—H7B | 0.96 | C39—C40 | 1.447 (9) |
C7—H7C | 0.96 | C39—C41 | 1.466 (9) |
C9—C10 | 1.508 (6) | C39—H39 | 0.98 |
C9—H9 | 0.98 | C40—H40A | 0.96 |
C10—C11 | 1.364 (6) | C40—H40B | 0.96 |
C10—C15 | 1.372 (6) | C40—H40C | 0.96 |
C11—C12 | 1.381 (8) | C41—H41A | 0.96 |
C11—H11 | 0.93 | C41—H41B | 0.96 |
C12—C13 | 1.381 (8) | C41—H41C | 0.96 |
C12—H12 | 0.93 | C42—C43 | 1.488 (10) |
C13—C14 | 1.354 (8) | C42—C44 | 1.529 (8) |
C13—C16 | 1.464 (9) | C42—H42 | 0.98 |
C14—C15 | 1.371 (7) | C43—H43A | 0.96 |
C14—H14 | 0.93 | C43—H43B | 0.96 |
C15—H15 | 0.93 | C43—H43C | 0.96 |
O2—C17 | 1.459 (9) | C43—H43D | 0.96 |
O2—C17' | 1.485 (10) | C43—H43E | 0.96 |
C17—C19 | 1.523 (10) | C43—H43F | 0.96 |
C17—C18 | 1.524 (9) | C44—H44A | 0.96 |
C17—H17A | 0.98 | C44—H44B | 0.96 |
C18—H18A | 0.96 | C44—H44C | 0.96 |
C18—H18B | 0.96 | | |
| | | |
O1—P1—O3 | 115.1 (2) | O3—C20—H20 | 108.3 |
O1—P1—O2 | 115.5 (2) | C22—C20—H20 | 108.3 |
O3—P1—O2 | 104.4 (2) | C21—C20—H20 | 108.3 |
O1—P1—C9 | 113.9 (2) | C20—C21—H21A | 109.5 |
O3—P1—C9 | 104.4 (2) | C20—C21—H21B | 109.5 |
O2—P1—C9 | 102.0 (2) | H21A—C21—H21B | 109.5 |
O4—P2—O6 | 108.0 (2) | C20—C21—H21C | 109.5 |
O4—P2—O5 | 114.9 (2) | H21A—C21—H21C | 109.5 |
O6—P2—O5 | 109.8 (2) | H21B—C21—H21C | 109.5 |
O4—P2—C31 | 113.8 (2) | C20—C22—H22A | 109.5 |
O6—P2—C31 | 107.4 (2) | C20—C22—H22B | 109.5 |
O5—P2—C31 | 102.5 (2) | H22A—C22—H22B | 109.5 |
C1—S1—C8 | 88.6 (3) | C20—C22—H22C | 109.5 |
C28—S2—C29 | 88.5 (3) | H22A—C22—H22C | 109.5 |
C20—O3—P1 | 123.8 (3) | H22B—C22—H22C | 109.5 |
C39—O5—P2 | 123.6 (3) | C24—C23—C28 | 120.4 (5) |
C42—O6—P2 | 126.3 (4) | C24—C23—N3 | 124.6 (5) |
C8—N1—C6 | 109.9 (4) | C28—C23—N3 | 115.0 (4) |
C8—N2—C9 | 121.6 (4) | C25—C24—C23 | 116.2 (5) |
C8—N2—H2A | 115 (3) | C25—C24—C30 | 122.1 (5) |
C9—N2—H2A | 123 (3) | C23—C24—C30 | 121.7 (5) |
C29—N3—C23 | 110.4 (4) | C26—C25—C24 | 123.3 (6) |
C29—N4—C31 | 121.3 (4) | C26—C25—H25 | 118.3 |
C29—N4—H4A | 122 (3) | C24—C25—H25 | 118.3 |
C31—N4—H4A | 117 (3) | C27—C26—C25 | 120.3 (6) |
C6—C1—C2 | 122.3 (5) | C27—C26—H26 | 119.8 |
C6—C1—S1 | 109.7 (4) | C25—C26—H26 | 119.8 |
C2—C1—S1 | 128.0 (5) | C26—C27—C28 | 118.4 (6) |
C3—C2—C1 | 117.0 (6) | C26—C27—H27 | 120.8 |
C3—C2—H2 | 121.5 | C28—C27—H27 | 120.8 |
C1—C2—H2 | 121.5 | C27—C28—C23 | 121.3 (5) |
C4—C3—C2 | 121.5 (7) | C27—C28—S2 | 129.1 (5) |
C4—C3—H3 | 119.2 | C23—C28—S2 | 109.7 (4) |
C2—C3—H3 | 119.2 | N3—C29—N4 | 124.4 (4) |
C3—C4—C5 | 121.9 (6) | N3—C29—S2 | 116.5 (4) |
C3—C4—H4 | 119.0 | N4—C29—S2 | 119.1 (4) |
C5—C4—H4 | 119.0 | C24—C30—H30A | 109.5 |
C4—C5—C6 | 117.5 (6) | C24—C30—H30B | 109.5 |
C4—C5—C7 | 121.0 (6) | H30A—C30—H30B | 109.5 |
C6—C5—C7 | 121.5 (5) | C24—C30—H30C | 109.5 |
C1—C6—N1 | 116.0 (5) | H30A—C30—H30C | 109.5 |
C1—C6—C5 | 119.7 (5) | H30B—C30—H30C | 109.5 |
N1—C6—C5 | 124.3 (5) | N4—C31—C32 | 113.3 (4) |
C5—C7—H7A | 109.5 | N4—C31—P2 | 109.3 (3) |
C5—C7—H7B | 109.5 | C32—C31—P2 | 112.3 (3) |
H7A—C7—H7B | 109.5 | N4—C31—H31 | 107.2 |
C5—C7—H7C | 109.5 | C32—C31—H31 | 107.2 |
H7A—C7—H7C | 109.5 | P2—C31—H31 | 107.2 |
H7B—C7—H7C | 109.5 | C33—C32—C37 | 118.6 (5) |
N1—C8—N2 | 125.2 (4) | C33—C32—C31 | 120.4 (4) |
N1—C8—S1 | 115.8 (4) | C37—C32—C31 | 120.9 (5) |
N2—C8—S1 | 119.0 (3) | C32—C33—C34 | 121.2 (6) |
N2—C9—C10 | 114.1 (4) | C32—C33—H33 | 119.4 |
N2—C9—P1 | 108.6 (3) | C34—C33—H33 | 119.4 |
C10—C9—P1 | 111.4 (3) | C35—C34—C33 | 120.2 (6) |
N2—C9—H9 | 107.5 | C35—C34—H34 | 119.9 |
C10—C9—H9 | 107.5 | C33—C34—H34 | 119.9 |
P1—C9—H9 | 107.5 | C34—C35—C36 | 120.1 (6) |
C11—C10—C15 | 118.2 (5) | C34—C35—C38 | 120.9 (7) |
C11—C10—C9 | 121.6 (4) | C36—C35—C38 | 119.0 (7) |
C15—C10—C9 | 120.2 (4) | C35—C36—C37 | 119.7 (5) |
C10—C11—C12 | 121.2 (5) | C35—C36—H36 | 120.2 |
C10—C11—H11 | 119.4 | C37—C36—H36 | 120.2 |
C12—C11—H11 | 119.4 | C32—C37—C36 | 120.2 (5) |
C11—C12—C13 | 119.4 (6) | C32—C37—H37 | 119.9 |
C11—C12—H12 | 120.3 | C36—C37—H37 | 119.9 |
C13—C12—H12 | 120.3 | F6—C38—F4 | 106.3 (8) |
C14—C13—C12 | 119.7 (6) | F4'—C38—F6' | 105.0 (10) |
C14—C13—C16 | 120.8 (7) | F4'—C38—F5' | 105.2 (11) |
C12—C13—C16 | 119.5 (7) | F6'—C38—F5' | 101.8 (9) |
C13—C14—C15 | 120.1 (5) | F6—C38—F5 | 104.6 (8) |
C13—C14—H14 | 119.9 | F4—C38—F5 | 103.9 (7) |
C15—C14—H14 | 119.9 | F6—C38—C35 | 116.1 (7) |
C14—C15—C10 | 121.4 (5) | F4—C38—C35 | 112.4 (7) |
C14—C15—H15 | 119.3 | F5—C38—C35 | 112.6 (7) |
C10—C15—H15 | 119.3 | C40—C39—O5 | 109.5 (6) |
F1—C16—F3 | 106.2 (10) | C40—C39—C41 | 114.5 (7) |
F2'—C16—F1' | 106.9 (9) | O5—C39—C41 | 108.2 (6) |
F1—C16—F2 | 107.6 (10) | C40—C39—H39 | 108.2 |
F3—C16—F2 | 103.9 (9) | O5—C39—H39 | 108.2 |
F2'—C16—F3' | 104.5 (9) | C41—C39—H39 | 108.2 |
F1'—C16—F3' | 101.9 (8) | C39—C40—H40A | 109.5 |
F1—C16—C13 | 110.8 (10) | C39—C40—H40B | 109.5 |
F3—C16—C13 | 113.9 (9) | H40A—C40—H40B | 109.5 |
F2—C16—C13 | 113.8 (9) | C39—C40—H40C | 109.5 |
C17—O2—P1 | 121.7 (7) | H40A—C40—H40C | 109.5 |
C17'—O2—P1 | 116.7 (8) | H40B—C40—H40C | 109.5 |
O2—C17—C19 | 104.0 (13) | C39—C41—H41A | 109.5 |
O2—C17—C18 | 109.1 (10) | C39—C41—H41B | 109.5 |
C19—C17—C18 | 113.2 (14) | H41A—C41—H41B | 109.5 |
O2—C17—H17A | 110.1 | C39—C41—H41C | 109.5 |
C19—C17—H17A | 110.1 | H41A—C41—H41C | 109.5 |
C18—C17—H17A | 110.1 | H41B—C41—H41C | 109.5 |
C17—C18—H18A | 109.5 | O6—C42—C43 | 109.7 (6) |
C17—C18—H18B | 109.5 | O6—C42—C44 | 106.6 (5) |
H18A—C18—H18B | 109.5 | C43—C42—C44 | 109.0 (7) |
C17—C18—H18C | 109.5 | O6—C42—H42 | 110.5 |
H18A—C18—H18C | 109.5 | C43—C42—H42 | 110.5 |
H18B—C18—H18C | 109.5 | C44—C42—H42 | 110.5 |
C17—C19—H19A | 109.5 | C42—C43—H43A | 109.5 |
C17—C19—H19B | 109.5 | C42—C43—H43B | 109.5 |
H19A—C19—H19B | 109.5 | H43A—C43—H43B | 109.5 |
C17—C19—H19C | 109.5 | C42—C43—H43C | 109.5 |
H19A—C19—H19C | 109.5 | H43A—C43—H43C | 109.5 |
H19B—C19—H19C | 109.5 | H43B—C43—H43C | 109.5 |
C19'—C17'—O2 | 112.9 (16) | C42—C43—H43D | 109.5 |
C19'—C17'—C18' | 105.8 (19) | H43A—C43—H43D | 141.1 |
O2—C17'—C18' | 105.8 (15) | H43B—C43—H43D | 56.3 |
C19'—C17'—H17B | 110.7 | H43C—C43—H43D | 56.3 |
O2—C17'—H17B | 110.7 | C42—C43—H43E | 109.5 |
C18'—C17'—H17B | 110.7 | H43A—C43—H43E | 56.3 |
C17'—C18'—H18D | 109.5 | H43B—C43—H43E | 141.1 |
C17'—C18'—H18E | 109.5 | H43C—C43—H43E | 56.3 |
H18D—C18'—H18E | 109.5 | H43D—C43—H43E | 109.5 |
C17'—C18'—H18F | 109.5 | C42—C43—H43F | 109.5 |
H18D—C18'—H18F | 109.5 | H43A—C43—H43F | 56.3 |
H18E—C18'—H18F | 109.5 | H43B—C43—H43F | 56.3 |
C17'—C19'—H19D | 109.5 | H43C—C43—H43F | 141.1 |
C17'—C19'—H19E | 109.5 | H43D—C43—H43F | 109.5 |
H19D—C19'—H19E | 109.5 | H43E—C43—H43F | 109.5 |
C17'—C19'—H19F | 109.5 | C42—C44—H44A | 109.5 |
H19D—C19'—H19F | 109.5 | C42—C44—H44B | 109.5 |
H19E—C19'—H19F | 109.5 | H44A—C44—H44B | 109.5 |
O3—C20—C22 | 109.8 (7) | C42—C44—H44C | 109.5 |
O3—C20—C21 | 106.9 (5) | H44A—C44—H44C | 109.5 |
C22—C20—C21 | 115.1 (6) | H44B—C44—H44C | 109.5 |
| | | |
O1—P1—O3—C20 | 4.4 (5) | C17'—O2—C17—C19 | 25.8 (16) |
O2—P1—O3—C20 | 132.0 (5) | P1—O2—C17—C19 | 122.5 (11) |
C9—P1—O3—C20 | −121.3 (5) | C17'—O2—C17—C18 | 147 (2) |
O4—P2—O5—C39 | −7.0 (5) | P1—O2—C17—C18 | −116.5 (10) |
O6—P2—O5—C39 | 115.1 (4) | C17—O2—C17'—C19' | −126 (2) |
C31—P2—O5—C39 | −130.9 (4) | P1—O2—C17'—C19' | 125.5 (16) |
O4—P2—O6—C42 | −175.8 (5) | C17—O2—C17'—C18' | −10.3 (15) |
O5—P2—O6—C42 | 58.2 (5) | P1—O2—C17'—C18' | −119.2 (15) |
C31—P2—O6—C42 | −52.6 (5) | P1—O3—C20—C22 | −94.3 (6) |
C8—S1—C1—C6 | 0.4 (4) | P1—O3—C20—C21 | 140.2 (5) |
C8—S1—C1—C2 | −178.9 (6) | C29—N3—C23—C24 | −178.9 (4) |
C6—C1—C2—C3 | 0.9 (10) | C29—N3—C23—C28 | −0.7 (6) |
S1—C1—C2—C3 | −179.9 (6) | C28—C23—C24—C25 | 1.6 (7) |
C1—C2—C3—C4 | −2.1 (12) | N3—C23—C24—C25 | 179.7 (4) |
C2—C3—C4—C5 | 2.0 (12) | C28—C23—C24—C30 | −178.8 (4) |
C3—C4—C5—C6 | −0.7 (10) | N3—C23—C24—C30 | −0.7 (7) |
C3—C4—C5—C7 | −179.5 (7) | C23—C24—C25—C26 | −2.0 (9) |
C2—C1—C6—N1 | 178.8 (5) | C30—C24—C25—C26 | 178.4 (6) |
S1—C1—C6—N1 | −0.6 (6) | C24—C25—C26—C27 | 2.3 (11) |
C2—C1—C6—C5 | 0.4 (9) | C25—C26—C27—C28 | −2.1 (11) |
S1—C1—C6—C5 | −179.0 (4) | C26—C27—C28—C23 | 1.8 (10) |
C8—N1—C6—C1 | 0.5 (6) | C26—C27—C28—S2 | −178.9 (5) |
C8—N1—C6—C5 | 178.8 (5) | C24—C23—C28—C27 | −1.6 (8) |
C4—C5—C6—C1 | −0.5 (8) | N3—C23—C28—C27 | −179.9 (5) |
C7—C5—C6—C1 | 178.3 (5) | C24—C23—C28—S2 | 178.9 (4) |
C4—C5—C6—N1 | −178.7 (5) | N3—C23—C28—S2 | 0.7 (5) |
C7—C5—C6—N1 | 0.1 (8) | C29—S2—C28—C27 | −179.7 (6) |
C6—N1—C8—N2 | −178.6 (4) | C29—S2—C28—C23 | −0.3 (4) |
C6—N1—C8—S1 | −0.2 (5) | C23—N3—C29—N4 | 179.8 (4) |
C9—N2—C8—N1 | 2.0 (7) | C23—N3—C29—S2 | 0.5 (5) |
C9—N2—C8—S1 | −176.4 (4) | C31—N4—C29—N3 | −1.6 (7) |
C1—S1—C8—N1 | −0.1 (4) | C31—N4—C29—S2 | 177.7 (3) |
C1—S1—C8—N2 | 178.4 (4) | C28—S2—C29—N3 | −0.1 (4) |
C8—N2—C9—C10 | −102.1 (5) | C28—S2—C29—N4 | −179.4 (4) |
C8—N2—C9—P1 | 133.1 (4) | C29—N4—C31—C32 | −96.5 (5) |
O1—P1—C9—N2 | 52.2 (4) | C29—N4—C31—P2 | 137.4 (4) |
O3—P1—C9—N2 | 178.6 (3) | O4—P2—C31—N4 | 70.0 (4) |
O2—P1—C9—N2 | −72.9 (3) | O6—P2—C31—N4 | −49.6 (4) |
O1—P1—C9—C10 | −74.2 (4) | O5—P2—C31—N4 | −165.3 (3) |
O3—P1—C9—C10 | 52.2 (4) | O4—P2—C31—C32 | −56.7 (4) |
O2—P1—C9—C10 | 160.7 (3) | O6—P2—C31—C32 | −176.2 (3) |
N2—C9—C10—C11 | −50.7 (6) | O5—P2—C31—C32 | 68.0 (4) |
P1—C9—C10—C11 | 72.6 (5) | N4—C31—C32—C33 | −51.7 (6) |
N2—C9—C10—C15 | 131.8 (4) | P2—C31—C32—C33 | 72.8 (5) |
P1—C9—C10—C15 | −104.9 (4) | N4—C31—C32—C37 | 125.9 (5) |
C15—C10—C11—C12 | 1.1 (8) | P2—C31—C32—C37 | −109.7 (4) |
C9—C10—C11—C12 | −176.4 (5) | C37—C32—C33—C34 | −1.2 (8) |
C10—C11—C12—C13 | −0.8 (10) | C31—C32—C33—C34 | 176.4 (5) |
C11—C12—C13—C14 | −0.1 (10) | C32—C33—C34—C35 | 0.7 (10) |
C11—C12—C13—C16 | −179.9 (6) | C33—C34—C35—C36 | 0.7 (10) |
C12—C13—C14—C15 | 0.5 (9) | C33—C34—C35—C38 | −180.0 (6) |
C16—C13—C14—C15 | −179.7 (6) | C34—C35—C36—C37 | −1.6 (9) |
C13—C14—C15—C10 | −0.1 (8) | C38—C35—C36—C37 | 179.1 (5) |
C11—C10—C15—C14 | −0.7 (7) | C33—C32—C37—C36 | 0.3 (7) |
C9—C10—C15—C14 | 176.9 (4) | C31—C32—C37—C36 | −177.3 (4) |
C14—C13—C16—F2' | −39.2 (14) | C35—C36—C37—C32 | 1.1 (8) |
C12—C13—C16—F2' | 140.6 (12) | C34—C35—C38—F6 | −75.5 (12) |
C14—C13—C16—F1 | 128.1 (14) | C36—C35—C38—F6 | 103.8 (11) |
C12—C13—C16—F1 | −52.1 (15) | C34—C35—C38—F4' | 124.3 (17) |
C14—C13—C16—F3 | −112.3 (13) | C36—C35—C38—F4' | −56.4 (18) |
C12—C13—C16—F3 | 67.5 (13) | C34—C35—C38—F4 | 47.1 (11) |
C14—C13—C16—F1' | 84.0 (10) | C36—C35—C38—F4 | −133.6 (9) |
C12—C13—C16—F1' | −96.2 (10) | C34—C35—C38—F6' | 0.0 (15) |
C14—C13—C16—F2 | 6.6 (13) | C36—C35—C38—F6' | 179.3 (14) |
C12—C13—C16—F2 | −173.6 (10) | C34—C35—C38—F5' | −112.4 (14) |
C14—C13—C16—F3' | −159.2 (9) | C36—C35—C38—F5' | 66.9 (14) |
C12—C13—C16—F3' | 20.6 (12) | C34—C35—C38—F5 | 164.0 (8) |
O1—P1—O2—C17 | 11.1 (8) | C36—C35—C38—F5 | −16.7 (11) |
O3—P1—O2—C17 | −116.3 (8) | P2—O5—C39—C40 | −104.5 (6) |
C9—P1—O2—C17 | 135.2 (8) | P2—O5—C39—C41 | 130.1 (5) |
O1—P1—O2—C17' | 61.0 (9) | P2—O6—C42—C43 | −101.6 (7) |
O3—P1—O2—C17' | −66.4 (9) | P2—O6—C42—C44 | 140.5 (5) |
C9—P1—O2—C17' | −174.9 (9) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O4i | 0.87 (5) | 1.91 (6) | 2.779 (7) | 170 (5) |
N4—H4A···O1ii | 0.90 (5) | 1.90 (6) | 2.774 (7) | 167 (6) |
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, −y+3/2, z+1/2. |