The new compound
N-(3-nitrobenzoyl)-
N′,
N′′-bis(
tert-butyl)phosphoric triamide was synthesized by reacting 3-nitrobenzoyl phosphoramidic dichloride and
tert-butyl amine, and characterized by multinuclear (
1H,
13C and
31P) NMR and FTIR spectroscopy techniques. Structural and conformational properties were analyzed using single-crystal X-ray diffraction, vibrational spectra and theoretical calculations. The crystal structure contains three symmetry-independent disordered molecules, connected
via intermolecular N—H
O=P and N—H
O=C hydrogen bonds to form a centrosymmetric hexameric chain extended along the [2,1,
] direction. The disorder is mainly caused by rotation of the
tert-butyl groups around the C—N bonds.
Supporting information
CCDC reference: 684213
Data collection: CrysAlis CCD (Oxford diffraction, 2007); cell refinement: CrysAlis RED (Oxford diffraction, 2007); data reduction: CrysAlis RED (Oxford diffraction, 2007); program(s) used to solve structure: Superflip(Palatinus L., Chapuis G., 2007); program(s) used to refine structure: Jana2006 (Petricek, Dusek & Palatinus, 2006); molecular graphics: Diamond (Brandenburg & Putz, 2005); software used to prepare material for publication: Jana2006 (Petricek, Dusek & Palatinus, 2006).
Crystal data top
C90H150N24O24P6 | Z = 1 |
Mr = 2138.16 | F(000) = 1140 |
Triclinic, P1 | Dx = 1.263 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 13.1528 (2) Å | Cell parameters from 14590 reflections |
b = 13.7179 (2) Å | θ = 2.6–39.3° |
c = 16.5876 (2) Å | µ = 0.17 mm−1 |
α = 87.8019 (12)° | T = 120 K |
β = 70.8182 (13)° | Irregular shape, pale yellow |
γ = 83.8446 (14)° | 0.67 × 0.26 × 0.22 mm |
V = 2810.41 (7) Å3 | |
Data collection top
Oxford Diffraction CCD diffractometer | 11679 independent reflections |
Radiation source: X-ray tube | 7286 reflections with I > 3σ(I) |
Graphite monochromator | Rint = 0.028 |
Detector resolution: 8.3438 pixels mm-1 | θmax = 26.5°, θmin = 2.8° |
Rotation method data acquisition using ω scans | h = −16→16 |
Absorption correction: multi-scan CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.16 (release 23-01-2008 CrysAlis171 .NET)
(compiled Jan 23 2008,18:08:03)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | k = −17→17 |
Tmin = 0.945, Tmax = 0.963 | l = −20→20 |
34749 measured reflections | |
Refinement top
Refinement on F | 300 constraints |
R[F2 > 2σ(F2)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.044 | Weighting scheme based on measured s.u.'s w = 1/(σ2(F) + 0.0001F2) |
S = 1.79 | (Δ/σ)max = 0.046 |
11679 reflections | Δρmax = 0.37 e Å−3 |
679 parameters | Δρmin = −0.35 e Å−3 |
0 restraints | |
Special details top
Refinement. The refinement was carried out against all reflections. The conventional
R-factor is always based on F. The goodness of fit as well as
the weighted R-factor are based on F and F2 for
refinement carried out on F and F2, respectively. The
threshold expression is used only for calculating R-factors etc.
and it is not relevant to the choice of reflections for refinement. The program used for refinement, Jana2006, uses the weighting scheme based on
the experimental expectations, see _refine_ls_weighting_details, that does not
force S to be one. Therefore the values of S are usually larger
then the ones from the SHELX program. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
P1 | 0.88086 (4) | 0.40917 (4) | 0.10429 (3) | 0.02764 (18) | |
P2 | 0.50902 (4) | 0.14229 (4) | 0.18806 (3) | 0.02790 (19) | |
P3 | 0.20898 (4) | 0.11482 (4) | 0.42939 (3) | 0.02812 (19) | |
O1 | 0.64239 (12) | 0.29458 (12) | −0.31107 (11) | 0.0607 (8) | |
O11 | 0.05296 (10) | −0.00015 (10) | 0.39539 (8) | 0.0370 (5) | |
O4 | 0.97334 (10) | 0.46291 (10) | 0.10079 (8) | 0.0379 (5) | |
O10 | −0.10680 (13) | −0.18281 (12) | 0.23778 (10) | 0.0554 (7) | |
O8 | 0.41323 (10) | 0.08718 (9) | 0.20723 (8) | 0.0344 (5) | |
O9 | −0.01813 (12) | −0.23171 (12) | 0.10865 (10) | 0.0592 (7) | |
O5 | 0.27968 (13) | 0.52456 (12) | 0.47006 (11) | 0.0646 (8) | |
O7 | 0.66664 (10) | 0.24902 (9) | 0.23026 (8) | 0.0337 (5) | |
N1 | 0.63704 (14) | 0.29631 (13) | −0.23609 (13) | 0.0443 (8) | |
N11 | 0.18432 (11) | 0.04104 (11) | 0.51124 (9) | 0.0278 (6) | |
N5 | 0.26939 (16) | 0.56268 (15) | 0.53776 (14) | 0.0557 (9) | |
O12 | 0.31085 (11) | 0.15909 (11) | 0.41082 (8) | 0.0484 (6) | |
O3 | 0.73101 (10) | 0.32642 (9) | 0.03265 (8) | 0.0342 (5) | |
O6 | 0.19059 (16) | 0.55881 (17) | 0.60175 (12) | 0.1027 (11) | |
N9 | −0.02620 (15) | −0.18767 (12) | 0.17387 (12) | 0.0413 (8) | |
O2 | 0.56822 (13) | 0.25917 (13) | −0.17757 (11) | 0.0630 (8) | |
N8 | 0.51104 (12) | 0.23592 (11) | 0.12389 (9) | 0.0327 (6) | |
N3 | 0.89290 (12) | 0.29342 (11) | 0.12757 (11) | 0.0414 (7) | |
N7 | 0.62500 (12) | 0.07758 (11) | 0.14506 (10) | 0.0326 (6) | |
N6 | 0.50668 (12) | 0.18549 (11) | 0.28423 (9) | 0.0285 (6) | |
N4 | 0.76491 (11) | 0.45248 (10) | 0.17169 (9) | 0.0271 (6) | |
N10 | 0.21783 (11) | 0.05329 (11) | 0.33994 (9) | 0.0278 (6) | |
N2 | 0.87127 (11) | 0.41812 (10) | 0.00427 (9) | 0.0278 (6) | |
C20 | 0.64141 (16) | 0.38284 (14) | 0.45655 (13) | 0.0353 (8) | |
C18 | 0.46852 (16) | 0.32945 (16) | 0.52213 (13) | 0.0441 (9) | |
N12 | 0.10135 (15) | 0.19181 (12) | 0.44507 (11) | 0.0473 (8) | |
C39a | 0.0732 (2) | 0.2911 (2) | 0.4804 (3) | 0.0328 (11) | 0.709 (14) |
C39b | 0.0810 (6) | 0.2788 (6) | 0.5014 (5) | 0.0328 (11) | 0.291 (14) |
C3 | 0.86794 (16) | 0.44105 (15) | −0.25575 (13) | 0.0425 (9) | |
C38 | 0.25833 (15) | −0.03726 (14) | 0.53150 (12) | 0.0359 (8) | |
C16 | 0.56882 (14) | 0.28674 (13) | 0.37565 (11) | 0.0276 (7) | |
C31 | 0.14952 (14) | −0.04617 (13) | 0.25189 (11) | 0.0276 (7) | |
C8 | 0.98429 (15) | 0.23395 (13) | 0.14361 (11) | 0.0339 (8) | |
C9a | 0.7228 (4) | 0.5575 (3) | 0.1958 (5) | 0.0293 (11) | 0.530 (17) |
C9b | 0.7163 (5) | 0.5564 (4) | 0.1746 (5) | 0.0293 (11) | 0.470 (17) |
C17 | 0.47647 (15) | 0.28345 (14) | 0.44706 (12) | 0.0362 (8) | |
C34 | 0.15470 (17) | −0.13395 (14) | 0.10106 (13) | 0.0378 (9) | |
C24 | 0.42503 (14) | 0.31796 (14) | 0.13302 (12) | 0.0327 (8) | |
C19 | 0.55164 (16) | 0.37941 (15) | 0.52804 (13) | 0.0389 (8) | |
C4 | 0.79066 (16) | 0.39602 (15) | −0.27713 (13) | 0.0398 (8) | |
C5 | 0.71873 (15) | 0.34629 (13) | −0.21364 (13) | 0.0323 (8) | |
C1 | 0.79765 (14) | 0.38574 (13) | −0.10969 (11) | 0.0271 (7) | |
C23 | 0.64395 (15) | −0.03201 (13) | 0.14509 (12) | 0.0383 (8) | |
C2 | 0.87213 (15) | 0.43590 (14) | −0.17329 (12) | 0.0344 (8) | |
C6 | 0.72022 (14) | 0.34082 (13) | −0.13113 (12) | 0.0296 (7) | |
C36 | 0.06258 (15) | −0.09452 (13) | 0.24985 (12) | 0.0278 (7) | |
C33 | 0.24160 (18) | −0.08738 (14) | 0.10364 (13) | 0.0419 (9) | |
C21 | 0.65208 (15) | 0.33799 (13) | 0.38127 (12) | 0.0332 (8) | |
C7 | 0.79748 (14) | 0.37470 (13) | −0.01909 (11) | 0.0279 (7) | |
C35 | 0.06708 (16) | −0.13687 (13) | 0.17467 (12) | 0.0313 (8) | |
C37 | 0.13701 (14) | 0.00310 (13) | 0.33431 (11) | 0.0275 (7) | |
C22 | 0.58387 (15) | 0.23881 (13) | 0.29190 (11) | 0.0281 (7) | |
C32 | 0.23946 (16) | −0.04328 (14) | 0.17842 (12) | 0.0339 (8) | |
H1c3 | 0.919147 | 0.476218 | −0.298676 | 0.051* | |
H1c4 | 0.787481 | 0.399422 | −0.334173 | 0.0478* | |
H1c6 | 0.668077 | 0.306157 | −0.088519 | 0.0355* | |
H1c2 | 0.926502 | 0.466946 | −0.159733 | 0.0413* | |
H1c17 | 0.417918 | 0.249044 | 0.444222 | 0.0435* | |
H1c18 | 0.404339 | 0.326585 | 0.570733 | 0.053* | |
H1c19 | 0.546862 | 0.410574 | 0.580181 | 0.0466* | |
H1c21 | 0.716352 | 0.341891 | 0.332919 | 0.0398* | |
H1c33 | 0.303985 | −0.085411 | 0.05343 | 0.0503* | |
H1c32 | 0.300106 | −0.010742 | 0.179441 | 0.0407* | |
H1c34 | 0.155265 | −0.163516 | 0.049374 | 0.0454* | |
H1c36 | 0.000494 | −0.098262 | 0.300043 | 0.0333* | |
H1n7 | 0.680662 | 0.109593 | 0.119933 | 0.0392* | |
H1n10 | 0.276475 | 0.054015 | 0.296068 | 0.0333* | |
H1n2 | 0.916033 | 0.452307 | −0.033747 | 0.0334* | |
H1n3 | 0.837462 | 0.262118 | 0.131054 | 0.0496* | |
H1n4 | 0.721482 | 0.408941 | 0.197183 | 0.0325* | |
H1n6 | 0.453886 | 0.172695 | 0.329888 | 0.0342* | |
H1n8 | 0.568922 | 0.237849 | 0.079502 | 0.0393* | |
H1n11 | 0.119142 | 0.048749 | 0.547731 | 0.0333* | |
H1n12 | 0.050974 | 0.169886 | 0.429522 | 0.0568* | |
C13a | 0.9597 (2) | 0.12773 (19) | 0.14475 (19) | 0.0571 (11) | |
C15a | 1.0891 (2) | 0.2489 (2) | 0.07210 (17) | 0.0537 (10) | |
C14a | 0.9930 (2) | 0.2605 (2) | 0.22893 (17) | 0.0645 (12) | |
H1c13a | 1.017164 | 0.085201 | 0.154891 | 0.0685* | |
H2c13a | 0.892892 | 0.119046 | 0.189329 | 0.0685* | |
H3c13a | 0.95351 | 0.112039 | 0.090752 | 0.0685* | |
H1c14a | 1.048792 | 0.217292 | 0.240744 | 0.0774* | |
H2c14a | 1.010403 | 0.326961 | 0.226914 | 0.0774* | |
H3c14a | 0.925195 | 0.25415 | 0.273092 | 0.0774* | |
H1c15a | 1.145949 | 0.202105 | 0.078009 | 0.0644* | |
H2c15a | 1.07959 | 0.24004 | 0.017991 | 0.0644* | |
H3c15a | 1.107855 | 0.314084 | 0.075211 | 0.0644* | |
C11a | 0.6031 (2) | 0.5591 (7) | 0.2446 (4) | 0.0478 (13) | 0.571 (3) |
C10a | 0.7786 (5) | 0.5987 (3) | 0.2520 (6) | 0.0542 (16) | 0.571 (3) |
C12a | 0.7402 (5) | 0.6177 (4) | 0.1139 (5) | 0.0519 (16) | 0.571 (3) |
H1c11a | 0.592472 | 0.514751 | 0.292176 | 0.0574* | 0.571 (3) |
H2c11a | 0.574649 | 0.624278 | 0.264999 | 0.0574* | 0.571 (3) |
H3c11a | 0.566261 | 0.539355 | 0.207598 | 0.0574* | 0.571 (3) |
H1c12a | 0.816269 | 0.616955 | 0.08376 | 0.0623* | 0.571 (3) |
H2c12a | 0.70571 | 0.590037 | 0.078602 | 0.0623* | 0.571 (3) |
H3c12a | 0.709426 | 0.6841 | 0.127927 | 0.0623* | 0.571 (3) |
H1c10a | 0.766703 | 0.560219 | 0.303253 | 0.065* | 0.571 (3) |
H2c10a | 0.854786 | 0.596534 | 0.221858 | 0.065* | 0.571 (3) |
H3c10a | 0.749442 | 0.66535 | 0.266442 | 0.065* | 0.571 (3) |
C11b | 0.6209 (4) | 0.5629 (7) | 0.2563 (4) | 0.0478 (14) | 0.429 (3) |
C10b | 0.7989 (6) | 0.6219 (4) | 0.1817 (4) | 0.0542 (18) | 0.429 (3) |
C12b | 0.6787 (6) | 0.5875 (4) | 0.0988 (4) | 0.0519 (18) | 0.429 (3) |
H1c11b | 0.643596 | 0.535657 | 0.302536 | 0.0574* | 0.429 (3) |
H2c11b | 0.593177 | 0.630326 | 0.268196 | 0.0574* | 0.429 (3) |
H3c11b | 0.565233 | 0.526842 | 0.250096 | 0.0574* | 0.429 (3) |
H1c12b | 0.739855 | 0.583888 | 0.047298 | 0.0623* | 0.429 (3) |
H2c12b | 0.627698 | 0.544605 | 0.094378 | 0.0623* | 0.429 (3) |
H3c12b | 0.644893 | 0.653604 | 0.106929 | 0.0623* | 0.429 (3) |
H1c10b | 0.821541 | 0.601561 | 0.229723 | 0.065* | 0.429 (3) |
H2c10b | 0.860385 | 0.616979 | 0.13052 | 0.065* | 0.429 (3) |
H3c10b | 0.766939 | 0.688617 | 0.189477 | 0.065* | 0.429 (3) |
C29a | 0.5900 (2) | −0.07471 (19) | 0.08806 (17) | 0.0509 (10) | |
C28a | 0.7666 (2) | −0.0570 (2) | 0.10879 (18) | 0.0511 (10) | |
C30a | 0.6013 (2) | −0.0737 (2) | 0.23590 (17) | 0.0660 (11) | |
H1c30a | 0.620379 | −0.143322 | 0.234728 | 0.0792* | |
H2c30a | 0.632925 | −0.043747 | 0.272089 | 0.0792* | |
H3c30a | 0.524046 | −0.060179 | 0.257655 | 0.0792* | |
H1c29a | 0.605168 | −0.144772 | 0.086442 | 0.0611* | |
H2c29a | 0.513197 | −0.057732 | 0.110373 | 0.0611* | |
H3c29a | 0.617508 | −0.048575 | 0.031394 | 0.0611* | |
H1c28a | 0.783187 | −0.126888 | 0.106546 | 0.0614* | |
H2c28a | 0.793057 | −0.030103 | 0.052308 | 0.0614* | |
H3c28a | 0.800356 | −0.029583 | 0.144737 | 0.0614* | |
C26a | 0.4717 (4) | 0.4036 (4) | 0.0734 (4) | 0.0578 (17) | 0.420 (2) |
C25a | 0.3379 (5) | 0.2798 (4) | 0.1096 (4) | 0.064 (2) | 0.420 (2) |
C27a | 0.3803 (6) | 0.3611 (5) | 0.2245 (3) | 0.0638 (19) | 0.420 (2) |
H1c27a | 0.335192 | 0.316481 | 0.26215 | 0.0766* | 0.420 (2) |
H2c27a | 0.439411 | 0.370841 | 0.244183 | 0.0766* | 0.420 (2) |
H3c27a | 0.338465 | 0.422818 | 0.223857 | 0.0766* | 0.420 (2) |
H1c26a | 0.414794 | 0.454922 | 0.076662 | 0.0694* | 0.420 (2) |
H2c26a | 0.52665 | 0.428535 | 0.090847 | 0.0694* | 0.420 (2) |
H3c26a | 0.502518 | 0.380429 | 0.015709 | 0.0694* | 0.420 (2) |
H1c25a | 0.313769 | 0.223958 | 0.144542 | 0.077* | 0.420 (2) |
H2c25a | 0.278463 | 0.329893 | 0.118237 | 0.077* | 0.420 (2) |
H3c25a | 0.364658 | 0.260787 | 0.050614 | 0.077* | 0.420 (2) |
C26b | 0.4355 (6) | 0.3555 (5) | 0.0442 (4) | 0.0578 (18) | 0.580 (2) |
C25b | 0.3114 (7) | 0.2849 (6) | 0.1760 (5) | 0.064 (2) | 0.580 (2) |
C27b | 0.4448 (7) | 0.3955 (6) | 0.1858 (5) | 0.064 (2) | 0.580 (2) |
H1c27b | 0.420899 | 0.379546 | 0.245466 | 0.0766* | 0.580 (2) |
H2c27b | 0.521064 | 0.401898 | 0.166836 | 0.0766* | 0.580 (2) |
H3c27b | 0.406632 | 0.456327 | 0.17655 | 0.0766* | 0.580 (2) |
H1c26b | 0.383579 | 0.411374 | 0.048268 | 0.0694* | 0.580 (2) |
H2c26b | 0.507266 | 0.374942 | 0.019296 | 0.0694* | 0.580 (2) |
H3c26b | 0.424214 | 0.306429 | 0.009172 | 0.0694* | 0.580 (2) |
H1c25b | 0.306284 | 0.254454 | 0.230065 | 0.077* | 0.580 (2) |
H2c25b | 0.260546 | 0.34237 | 0.18461 | 0.077* | 0.580 (2) |
H3c25b | 0.295324 | 0.239678 | 0.140141 | 0.077* | 0.580 (2) |
C44a | 0.2131 (6) | −0.0621 (5) | 0.6246 (3) | 0.070 (2) | 0.519 (4) |
C43a | 0.3701 (5) | −0.0051 (5) | 0.5130 (6) | 0.093 (3) | 0.519 (4) |
C45a | 0.2627 (6) | −0.1245 (4) | 0.4773 (4) | 0.084 (3) | 0.519 (4) |
H1c45a | 0.311778 | −0.176695 | 0.487496 | 0.101* | 0.519 (4) |
H2c45a | 0.191797 | −0.146176 | 0.491778 | 0.101* | 0.519 (4) |
H3c45a | 0.287193 | −0.106184 | 0.418093 | 0.101* | 0.519 (4) |
H1c44a | 0.205272 | −0.004486 | 0.658009 | 0.0844* | 0.519 (4) |
H2c44a | 0.143725 | −0.085993 | 0.636035 | 0.0844* | 0.519 (4) |
H3c44a | 0.261395 | −0.111732 | 0.639203 | 0.0844* | 0.519 (4) |
H1c43a | 0.401135 | 0.006835 | 0.452862 | 0.1122* | 0.519 (4) |
H2c43a | 0.365236 | 0.053911 | 0.54382 | 0.1122* | 0.519 (4) |
H3c43a | 0.414898 | −0.055723 | 0.53038 | 0.1122* | 0.519 (4) |
C44b | 0.1881 (7) | −0.0993 (8) | 0.6006 (6) | 0.070 (2) | 0.481 (4) |
C43b | 0.3258 (7) | 0.0161 (8) | 0.5747 (8) | 0.093 (4) | 0.481 (4) |
C45b | 0.3311 (7) | −0.0967 (8) | 0.4597 (7) | 0.084 (3) | 0.481 (4) |
H1c45b | 0.379456 | −0.142446 | 0.478244 | 0.101* | 0.481 (4) |
H2c45b | 0.287549 | −0.13178 | 0.436748 | 0.101* | 0.481 (4) |
H3c45b | 0.372213 | −0.054476 | 0.416541 | 0.101* | 0.481 (4) |
H1c44b | 0.138497 | −0.058954 | 0.645526 | 0.0844* | 0.481 (4) |
H2c44b | 0.148199 | −0.135213 | 0.57471 | 0.0844* | 0.481 (4) |
H3c44b | 0.232277 | −0.144474 | 0.623847 | 0.0844* | 0.481 (4) |
H1c43b | 0.374411 | 0.053551 | 0.531832 | 0.1122* | 0.481 (4) |
H2c43b | 0.278964 | 0.059145 | 0.618709 | 0.1122* | 0.481 (4) |
H3c43b | 0.366653 | −0.03145 | 0.598856 | 0.1122* | 0.481 (4) |
C40a | 0.1090 (4) | 0.2965 (3) | 0.5592 (4) | 0.0517 (15) | 0.756 (3) |
C41a | −0.0481 (3) | 0.3178 (3) | 0.5052 (4) | 0.0695 (17) | 0.756 (3) |
C42a | 0.1323 (4) | 0.3590 (3) | 0.4116 (4) | 0.0605 (16) | 0.756 (3) |
H1c40a | 0.093854 | 0.362455 | 0.580312 | 0.062* | 0.756 (3) |
H2c40a | 0.070231 | 0.2533 | 0.602657 | 0.062* | 0.756 (3) |
H3c40a | 0.185207 | 0.277051 | 0.54378 | 0.062* | 0.756 (3) |
H1c42a | 0.11709 | 0.425006 | 0.432666 | 0.0725* | 0.756 (3) |
H2c42a | 0.208694 | 0.340029 | 0.395365 | 0.0725* | 0.756 (3) |
H3c42a | 0.108774 | 0.35521 | 0.362923 | 0.0725* | 0.756 (3) |
H1c41a | −0.065767 | 0.383818 | 0.526146 | 0.0833* | 0.756 (3) |
H2c41a | −0.070518 | 0.312601 | 0.456066 | 0.0833* | 0.756 (3) |
H3c41a | −0.084758 | 0.273801 | 0.548879 | 0.0833* | 0.756 (3) |
C40b | 0.1495 (4) | 0.2849 (3) | 0.5598 (3) | 0.0517 (18) | 0.244 (3) |
C41b | −0.0310 (3) | 0.2526 (3) | 0.5538 (3) | 0.0695 (17) | 0.244 (3) |
C42b | 0.0733 (4) | 0.3747 (3) | 0.4556 (3) | 0.0605 (17) | 0.244 (3) |
H1c40b | 0.116947 | 0.33611 | 0.600841 | 0.062* | 0.244 (3) |
H2c40b | 0.153244 | 0.223477 | 0.588905 | 0.062* | 0.244 (3) |
H3c40b | 0.221124 | 0.298906 | 0.526088 | 0.062* | 0.244 (3) |
H1c42b | 0.040569 | 0.425971 | 0.4966 | 0.0725* | 0.244 (3) |
H2c42b | 0.144425 | 0.389378 | 0.42131 | 0.0725* | 0.244 (3) |
H3c42b | 0.029833 | 0.370015 | 0.419597 | 0.0725* | 0.244 (3) |
H1c41b | −0.065977 | 0.302907 | 0.595292 | 0.0833* | 0.244 (3) |
H2c41b | −0.072958 | 0.247076 | 0.516861 | 0.0833* | 0.244 (3) |
H3c41b | −0.024833 | 0.191205 | 0.582482 | 0.0833* | 0.244 (3) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0212 (3) | 0.0252 (3) | 0.0338 (3) | −0.0081 (2) | −0.0045 (2) | 0.0091 (2) |
P2 | 0.0264 (3) | 0.0274 (3) | 0.0264 (3) | −0.0057 (2) | −0.0029 (2) | −0.0010 (2) |
P3 | 0.0312 (3) | 0.0283 (3) | 0.0247 (3) | −0.0109 (2) | −0.0067 (2) | 0.0019 (2) |
O1 | 0.0618 (11) | 0.0792 (13) | 0.0508 (11) | −0.0141 (9) | −0.0289 (9) | −0.0041 (9) |
O11 | 0.0263 (7) | 0.0505 (9) | 0.0317 (8) | −0.0134 (7) | −0.0021 (6) | −0.0086 (6) |
O4 | 0.0284 (8) | 0.0458 (9) | 0.0429 (8) | −0.0197 (7) | −0.0137 (6) | 0.0222 (7) |
O10 | 0.0568 (11) | 0.0629 (11) | 0.0538 (11) | −0.0246 (9) | −0.0213 (9) | −0.0081 (8) |
O8 | 0.0286 (7) | 0.0398 (8) | 0.0314 (8) | −0.0118 (6) | −0.0021 (6) | −0.0054 (6) |
O9 | 0.0624 (11) | 0.0637 (11) | 0.0646 (11) | 0.0088 (9) | −0.0392 (9) | −0.0345 (9) |
O5 | 0.0749 (12) | 0.0683 (12) | 0.0643 (12) | −0.0240 (10) | −0.0343 (10) | −0.0149 (9) |
O7 | 0.0288 (7) | 0.0394 (8) | 0.0291 (7) | −0.0140 (6) | −0.0014 (6) | 0.0025 (6) |
N1 | 0.0404 (11) | 0.0449 (12) | 0.0520 (13) | −0.0046 (9) | −0.0213 (10) | 0.0030 (9) |
N11 | 0.0191 (8) | 0.0351 (9) | 0.0243 (9) | −0.0043 (7) | −0.0003 (6) | 0.0026 (7) |
N5 | 0.0576 (14) | 0.0610 (14) | 0.0562 (14) | −0.0258 (11) | −0.0220 (11) | −0.0063 (11) |
O12 | 0.0507 (9) | 0.0651 (10) | 0.0280 (8) | −0.0400 (8) | 0.0001 (7) | −0.0026 (7) |
O3 | 0.0332 (8) | 0.0334 (8) | 0.0314 (8) | −0.0169 (6) | −0.0004 (6) | 0.0026 (6) |
O6 | 0.0784 (14) | 0.157 (2) | 0.0728 (14) | −0.0808 (15) | −0.0002 (11) | −0.0302 (13) |
N9 | 0.0513 (12) | 0.0339 (10) | 0.0484 (12) | 0.0020 (9) | −0.0304 (10) | −0.0087 (9) |
O2 | 0.0560 (11) | 0.0791 (13) | 0.0667 (12) | −0.0347 (10) | −0.0306 (9) | 0.0196 (10) |
N8 | 0.0230 (9) | 0.0373 (10) | 0.0277 (9) | 0.0020 (8) | 0.0036 (7) | 0.0036 (7) |
N3 | 0.0226 (9) | 0.0280 (10) | 0.0667 (12) | −0.0071 (8) | −0.0062 (8) | 0.0189 (9) |
N7 | 0.0266 (9) | 0.0235 (9) | 0.0420 (10) | −0.0069 (7) | −0.0019 (7) | −0.0011 (7) |
N6 | 0.0284 (9) | 0.0292 (9) | 0.0240 (9) | −0.0132 (7) | −0.0005 (7) | 0.0029 (7) |
N4 | 0.0255 (9) | 0.0221 (9) | 0.0311 (9) | −0.0114 (7) | −0.0033 (7) | 0.0036 (7) |
N10 | 0.0223 (9) | 0.0340 (9) | 0.0244 (9) | −0.0089 (7) | −0.0021 (7) | −0.0012 (7) |
N2 | 0.0236 (9) | 0.0255 (9) | 0.0281 (9) | −0.0096 (7) | 0.0017 (7) | 0.0055 (7) |
C20 | 0.0382 (12) | 0.0286 (11) | 0.0434 (13) | −0.0108 (10) | −0.0172 (10) | 0.0021 (9) |
C18 | 0.0360 (13) | 0.0591 (15) | 0.0327 (13) | −0.0079 (11) | −0.0029 (10) | −0.0102 (11) |
N12 | 0.0632 (13) | 0.0326 (10) | 0.0532 (12) | 0.0095 (9) | −0.0318 (10) | −0.0106 (9) |
C39a | 0.0410 (14) | 0.0272 (15) | 0.029 (2) | 0.0005 (11) | −0.0108 (12) | −0.0005 (14) |
C39b | 0.0410 (14) | 0.0272 (15) | 0.029 (2) | 0.0005 (11) | −0.0108 (12) | −0.0005 (14) |
C3 | 0.0442 (13) | 0.0448 (14) | 0.0315 (13) | −0.0136 (11) | −0.0009 (10) | 0.0076 (10) |
C38 | 0.0310 (12) | 0.0368 (12) | 0.0385 (12) | 0.0005 (10) | −0.0113 (9) | 0.0072 (9) |
C16 | 0.0299 (11) | 0.0244 (10) | 0.0285 (11) | −0.0069 (9) | −0.0085 (8) | 0.0036 (8) |
C31 | 0.0307 (11) | 0.0231 (10) | 0.0288 (11) | −0.0002 (9) | −0.0103 (8) | −0.0005 (8) |
C8 | 0.0421 (13) | 0.0303 (11) | 0.0299 (11) | 0.0036 (10) | −0.0153 (9) | 0.0030 (9) |
C9a | 0.0310 (13) | 0.0259 (12) | 0.030 (2) | −0.0041 (10) | −0.0086 (14) | −0.0009 (13) |
C9b | 0.0310 (13) | 0.0259 (12) | 0.030 (2) | −0.0041 (10) | −0.0086 (14) | −0.0009 (13) |
C17 | 0.0312 (12) | 0.0427 (13) | 0.0334 (12) | −0.0114 (10) | −0.0058 (9) | −0.0059 (10) |
C34 | 0.0619 (15) | 0.0233 (11) | 0.0303 (12) | 0.0038 (10) | −0.0195 (11) | −0.0048 (9) |
C24 | 0.0243 (11) | 0.0332 (12) | 0.0375 (12) | 0.0016 (9) | −0.0073 (9) | 0.0010 (9) |
C19 | 0.0469 (13) | 0.0377 (12) | 0.0351 (13) | −0.0016 (11) | −0.0175 (10) | −0.0086 (10) |
C4 | 0.0438 (13) | 0.0422 (13) | 0.0318 (12) | −0.0027 (11) | −0.0107 (10) | 0.0016 (10) |
C5 | 0.0302 (11) | 0.0266 (11) | 0.0397 (13) | 0.0016 (9) | −0.0122 (9) | −0.0014 (9) |
C1 | 0.0250 (10) | 0.0202 (10) | 0.0303 (11) | −0.0011 (8) | −0.0016 (8) | −0.0007 (8) |
C23 | 0.0446 (13) | 0.0267 (11) | 0.0369 (12) | −0.0005 (10) | −0.0053 (10) | 0.0004 (9) |
C2 | 0.0345 (12) | 0.0318 (12) | 0.0332 (12) | −0.0099 (9) | −0.0042 (9) | 0.0005 (9) |
C6 | 0.0255 (11) | 0.0226 (10) | 0.0348 (12) | 0.0004 (9) | −0.0033 (9) | 0.0037 (8) |
C36 | 0.0301 (11) | 0.0236 (10) | 0.0298 (11) | 0.0016 (9) | −0.0113 (9) | −0.0005 (8) |
C33 | 0.0535 (15) | 0.0324 (12) | 0.0314 (12) | −0.0026 (11) | −0.0028 (10) | −0.0012 (9) |
C21 | 0.0322 (12) | 0.0330 (12) | 0.0341 (12) | −0.0085 (10) | −0.0092 (9) | 0.0033 (9) |
C7 | 0.0247 (10) | 0.0202 (10) | 0.0325 (11) | −0.0037 (8) | −0.0005 (8) | 0.0004 (8) |
C35 | 0.0415 (12) | 0.0200 (10) | 0.0369 (12) | 0.0026 (9) | −0.0203 (10) | −0.0019 (8) |
C37 | 0.0259 (11) | 0.0273 (11) | 0.0298 (11) | −0.0034 (9) | −0.0093 (9) | −0.0002 (8) |
C22 | 0.0297 (11) | 0.0244 (10) | 0.0288 (11) | −0.0068 (9) | −0.0069 (9) | 0.0059 (8) |
C32 | 0.0369 (12) | 0.0301 (11) | 0.0323 (12) | −0.0049 (9) | −0.0074 (9) | −0.0013 (9) |
C13a | 0.0732 (18) | 0.0323 (13) | 0.0767 (19) | 0.0063 (12) | −0.0430 (15) | −0.0002 (12) |
C15a | 0.0323 (13) | 0.0719 (18) | 0.0559 (15) | 0.0093 (12) | −0.0162 (11) | −0.0147 (13) |
C14a | 0.105 (2) | 0.0589 (17) | 0.0387 (14) | −0.0304 (15) | −0.0305 (14) | 0.0104 (12) |
C11a | 0.0423 (18) | 0.0426 (16) | 0.048 (2) | 0.0023 (16) | −0.0022 (16) | −0.008 (2) |
C10a | 0.062 (3) | 0.038 (2) | 0.065 (3) | −0.0041 (18) | −0.023 (2) | −0.0215 (19) |
C12a | 0.068 (3) | 0.0314 (19) | 0.047 (2) | 0.0073 (19) | −0.0100 (17) | 0.0069 (16) |
C11b | 0.053 (2) | 0.041 (2) | 0.0413 (18) | 0.0040 (19) | −0.0059 (15) | −0.0081 (17) |
C10b | 0.062 (3) | 0.027 (2) | 0.072 (2) | −0.010 (2) | −0.0175 (19) | −0.0073 (16) |
C12b | 0.069 (4) | 0.040 (2) | 0.0484 (19) | 0.016 (2) | −0.028 (2) | −0.0004 (16) |
C29a | 0.0527 (15) | 0.0348 (13) | 0.0572 (15) | −0.0141 (12) | −0.0031 (12) | −0.0090 (11) |
C28a | 0.0515 (14) | 0.0342 (13) | 0.0620 (16) | 0.0080 (11) | −0.0141 (12) | −0.0053 (11) |
C30a | 0.085 (2) | 0.0497 (16) | 0.0481 (15) | 0.0060 (15) | −0.0058 (13) | 0.0119 (12) |
C26a | 0.0435 (19) | 0.046 (3) | 0.076 (3) | 0.0054 (17) | −0.013 (2) | 0.019 (2) |
C25a | 0.043 (3) | 0.059 (2) | 0.106 (4) | 0.0002 (19) | −0.047 (3) | 0.000 (3) |
C27a | 0.064 (3) | 0.055 (3) | 0.063 (2) | 0.0289 (19) | −0.017 (2) | −0.015 (2) |
C26b | 0.059 (3) | 0.058 (2) | 0.048 (2) | 0.021 (2) | −0.0140 (19) | 0.0069 (17) |
C25b | 0.025 (4) | 0.066 (3) | 0.089 (3) | 0.005 (2) | −0.007 (2) | 0.0130 (19) |
C27b | 0.073 (4) | 0.036 (3) | 0.086 (2) | 0.018 (2) | −0.036 (2) | −0.0159 (18) |
C44a | 0.093 (4) | 0.068 (5) | 0.0421 (19) | 0.027 (3) | −0.023 (2) | 0.010 (2) |
C43a | 0.035 (2) | 0.082 (4) | 0.164 (7) | 0.001 (3) | −0.039 (4) | 0.033 (4) |
C45a | 0.125 (6) | 0.045 (3) | 0.096 (4) | 0.046 (4) | −0.069 (4) | −0.026 (3) |
C44b | 0.060 (3) | 0.069 (4) | 0.068 (4) | 0.007 (3) | −0.009 (2) | 0.038 (3) |
C43b | 0.094 (3) | 0.073 (5) | 0.158 (8) | −0.002 (3) | −0.104 (4) | 0.003 (5) |
C45b | 0.083 (4) | 0.087 (3) | 0.062 (7) | 0.059 (3) | −0.017 (4) | −0.001 (4) |
C40a | 0.071 (3) | 0.045 (2) | 0.0412 (16) | −0.010 (2) | −0.020 (2) | −0.0064 (14) |
C41a | 0.060 (2) | 0.052 (2) | 0.091 (3) | 0.0190 (18) | −0.021 (2) | −0.0291 (19) |
C42a | 0.101 (3) | 0.0328 (19) | 0.045 (2) | −0.0119 (19) | −0.0184 (19) | 0.0074 (15) |
C40b | 0.069 (3) | 0.048 (3) | 0.0437 (17) | −0.001 (2) | −0.0269 (19) | −0.0083 (15) |
C41b | 0.052 (3) | 0.081 (3) | 0.058 (2) | 0.0003 (19) | 0.0061 (19) | −0.0287 (18) |
C42b | 0.091 (3) | 0.038 (2) | 0.0539 (19) | 0.020 (2) | −0.0330 (18) | −0.0057 (15) |
Geometric parameters (Å, º) top
P1—O4 | 1.4727 (15) | C36—C35 | 1.377 (3) |
P1—N3 | 1.6232 (16) | C36—H1c36 | 0.96 |
P1—N4 | 1.6324 (13) | C33—C32 | 1.392 (3) |
P1—N2 | 1.7036 (17) | C33—H1c33 | 0.96 |
P2—O8 | 1.4774 (14) | C21—H1c21 | 0.96 |
P2—N8 | 1.6332 (16) | C32—H1c32 | 0.96 |
P2—N7 | 1.6330 (14) | C13a—H1c13a | 0.96 |
P2—N6 | 1.7127 (17) | C13a—H2c13a | 0.96 |
P3—N11 | 1.6275 (15) | C13a—H3c13a | 0.96 |
P3—O12 | 1.4656 (16) | C15a—H1c15a | 0.96 |
P3—N10 | 1.6996 (16) | C15a—H2c15a | 0.96 |
P3—N12 | 1.6265 (18) | C15a—H3c15a | 0.96 |
O1—N1 | 1.224 (3) | C14a—H1c14a | 0.96 |
O11—C37 | 1.2337 (19) | C14a—H2c14a | 0.96 |
O10—N9 | 1.226 (2) | C14a—H3c14a | 0.96 |
O9—N9 | 1.228 (3) | C11a—H1c11a | 0.96 |
O5—N5 | 1.218 (3) | C11a—H2c11a | 0.96 |
O7—C22 | 1.2411 (19) | C11a—H3c11a | 0.96 |
N1—O2 | 1.227 (2) | C10a—H1c10a | 0.96 |
N1—C5 | 1.485 (3) | C10a—H2c10a | 0.96 |
N11—C38 | 1.476 (3) | C10a—H3c10a | 0.96 |
N11—H1n11 | 0.87 | C12a—H1c12a | 0.96 |
N5—O6 | 1.220 (3) | C12a—H2c12a | 0.96 |
N5—C20i | 1.487 (3) | C12a—H3c12a | 0.96 |
O3—C7 | 1.236 (2) | C11b—H1c11b | 0.96 |
N9—C35 | 1.478 (3) | C11b—H2c11b | 0.96 |
N8—C24 | 1.482 (2) | C11b—H3c11b | 0.96 |
N8—H1n8 | 0.87 | C10b—H1c10b | 0.96 |
N3—C8 | 1.471 (3) | C10b—H2c10b | 0.96 |
N3—H1n3 | 0.87 | C10b—H3c10b | 0.96 |
N7—C23 | 1.497 (2) | C12b—H1c12b | 0.96 |
N7—H1n7 | 0.87 | C12b—H2c12b | 0.96 |
N6—C22 | 1.354 (3) | C12b—H3c12b | 0.96 |
N6—H1n6 | 0.87 | C29a—H1c29a | 0.96 |
N4—H1n4 | 0.87 | C29a—H2c29a | 0.96 |
N10—C37 | 1.356 (3) | C29a—H3c29a | 0.96 |
N10—H1n10 | 0.87 | C28a—H1c28a | 0.96 |
N2—C7 | 1.355 (3) | C28a—H2c28a | 0.96 |
N2—H1n2 | 0.87 | C28a—H3c28a | 0.96 |
C20—C19 | 1.375 (3) | C30a—H1c30a | 0.96 |
C20—C21 | 1.372 (3) | C30a—H2c30a | 0.96 |
C18—C17 | 1.386 (3) | C30a—H3c30a | 0.96 |
C18—C19 | 1.382 (3) | C26a—H1c26a | 0.96 |
C18—H1c18 | 0.96 | C26a—H2c26a | 0.96 |
N12—H1n12 | 0.87 | C26a—H3c26a | 0.96 |
C39a—C40a | 1.533 (8) | C25a—H1c25a | 0.96 |
C39a—C41a | 1.518 (4) | C25a—H2c25a | 0.96 |
C39a—C42a | 1.505 (6) | C25a—H3c25a | 0.96 |
C39b—C40b | 1.533 (11) | C27a—H1c27a | 0.96 |
C39b—C41b | 1.518 (8) | C27a—H2c27a | 0.96 |
C39b—C42b | 1.505 (9) | C27a—H3c27a | 0.96 |
C3—C4 | 1.389 (3) | C26b—H1c26b | 0.96 |
C3—C2 | 1.386 (3) | C26b—H2c26b | 0.96 |
C3—H1c3 | 0.96 | C26b—H3c26b | 0.96 |
C38—C44a | 1.501 (5) | C25b—H1c25b | 0.96 |
C38—C43a | 1.510 (7) | C25b—H2c25b | 0.96 |
C38—C45a | 1.510 (7) | C25b—H3c25b | 0.96 |
C38—C44b | 1.514 (10) | C27b—H1c27b | 0.96 |
C38—C43b | 1.559 (13) | C27b—H2c27b | 0.96 |
C38—C45b | 1.468 (10) | C27b—H3c27b | 0.96 |
C16—C17 | 1.394 (2) | C44a—H1c44a | 0.96 |
C16—C21 | 1.393 (3) | C44a—H2c44a | 0.96 |
C16—C22 | 1.504 (3) | C44a—H3c44a | 0.96 |
C31—C36 | 1.392 (3) | C43a—H1c43a | 0.96 |
C31—C37 | 1.501 (3) | C43a—H2c43a | 0.96 |
C31—C32 | 1.395 (2) | C43a—H3c43a | 0.96 |
C8—C13a | 1.524 (3) | C45a—H1c45a | 0.96 |
C8—C15a | 1.522 (3) | C45a—H2c45a | 0.96 |
C8—C14a | 1.518 (4) | C45a—H3c45a | 0.96 |
C9a—C11a | 1.513 (6) | C44b—H1c44b | 0.96 |
C9a—C10a | 1.518 (12) | C44b—H2c44b | 0.96 |
C9a—C12a | 1.526 (10) | C44b—H3c44b | 0.96 |
C9b—C11b | 1.513 (8) | C43b—H1c43b | 0.96 |
C9b—C10b | 1.518 (10) | C43b—H2c43b | 0.96 |
C9b—C12b | 1.526 (11) | C43b—H3c43b | 0.96 |
C17—H1c17 | 0.96 | C45b—H1c45b | 0.96 |
C34—C33 | 1.381 (3) | C45b—H2c45b | 0.96 |
C34—C35 | 1.379 (2) | C45b—H3c45b | 0.96 |
C34—H1c34 | 0.96 | C40a—H1c40a | 0.96 |
C24—C26a | 1.550 (6) | C40a—H2c40a | 0.96 |
C24—C25a | 1.475 (7) | C40a—H3c40a | 0.96 |
C24—C27a | 1.552 (5) | C41a—H1c41a | 0.96 |
C24—C26b | 1.508 (8) | C41a—H2c41a | 0.96 |
C24—C25b | 1.539 (9) | C41a—H3c41a | 0.96 |
C24—C27b | 1.499 (9) | C42a—H1c42a | 0.96 |
C19—H1c19 | 0.96 | C42a—H2c42a | 0.96 |
C4—C5 | 1.378 (3) | C42a—H3c42a | 0.96 |
C4—H1c4 | 0.96 | C40b—H1c40b | 0.96 |
C5—C6 | 1.374 (3) | C40b—H2c40b | 0.96 |
C1—C2 | 1.398 (2) | C40b—H3c40b | 0.96 |
C1—C6 | 1.390 (3) | C41b—H1c41b | 0.96 |
C1—C7 | 1.504 (3) | C41b—H2c41b | 0.96 |
C23—C29a | 1.521 (4) | C41b—H3c41b | 0.96 |
C23—C28a | 1.530 (3) | C42b—H1c42b | 0.96 |
C23—C30a | 1.536 (3) | C42b—H2c42b | 0.96 |
C2—H1c2 | 0.96 | C42b—H3c42b | 0.96 |
C6—H1c6 | 0.96 | | |
| | | |
O4—P1—N3 | 115.50 (9) | O3—C7—N2 | 121.03 (18) |
O4—P1—N4 | 115.07 (8) | O3—C7—C1 | 120.06 (18) |
O4—P1—N2 | 105.46 (8) | N2—C7—C1 | 118.91 (15) |
N3—P1—N4 | 104.82 (7) | N9—C35—C34 | 119.28 (19) |
N3—P1—N2 | 107.50 (9) | N9—C35—C36 | 118.04 (15) |
N4—P1—N2 | 108.13 (8) | C34—C35—C36 | 122.7 (2) |
O8—P2—N8 | 115.23 (9) | O11—C37—N10 | 120.59 (17) |
O8—P2—N7 | 114.93 (8) | O11—C37—C31 | 120.15 (18) |
O8—P2—N6 | 105.64 (7) | N10—C37—C31 | 119.23 (14) |
N8—P2—N7 | 104.58 (7) | O7—C22—N6 | 120.57 (17) |
N8—P2—N6 | 107.93 (8) | O7—C22—C16 | 119.70 (18) |
N7—P2—N6 | 108.23 (9) | N6—C22—C16 | 119.73 (14) |
N11—P3—O12 | 113.73 (9) | C31—C32—C33 | 120.2 (2) |
N11—P3—N10 | 110.25 (8) | C31—C32—H1c32 | 119.881 |
N11—P3—N12 | 106.55 (8) | C33—C32—H1c32 | 119.882 |
O12—P3—N10 | 106.39 (7) | C8—C13a—H1c13a | 109.471 |
O12—P3—N12 | 115.46 (9) | C8—C13a—H2c13a | 109.471 |
N10—P3—N12 | 104.01 (9) | C8—C13a—H3c13a | 109.471 |
O1—N1—O2 | 124.3 (2) | H1c13a—C13a—H2c13a | 109.471 |
O1—N1—C5 | 118.44 (16) | H1c13a—C13a—H3c13a | 109.471 |
O2—N1—C5 | 117.3 (2) | H2c13a—C13a—H3c13a | 109.471 |
P3—N11—C38 | 128.31 (11) | C8—C15a—H1c15a | 109.471 |
P3—N11—H1n11 | 115.843 | C8—C15a—H2c15a | 109.471 |
C38—N11—H1n11 | 115.842 | C8—C15a—H3c15a | 109.471 |
O5—N5—O6 | 124.3 (2) | H1c15a—C15a—H2c15a | 109.47 |
O5—N5—C20i | 118.21 (17) | H1c15a—C15a—H3c15a | 109.472 |
O6—N5—C20i | 117.5 (2) | H2c15a—C15a—H3c15a | 109.471 |
O10—N9—O9 | 124.1 (2) | C8—C14a—H1c14a | 109.471 |
O10—N9—C35 | 118.30 (19) | C8—C14a—H2c14a | 109.471 |
O9—N9—C35 | 117.62 (15) | C8—C14a—H3c14a | 109.471 |
P2—N8—C24 | 127.10 (11) | H1c14a—C14a—H2c14a | 109.471 |
P2—N8—H1n8 | 116.447 | H1c14a—C14a—H3c14a | 109.471 |
C24—N8—H1n8 | 116.448 | H2c14a—C14a—H3c14a | 109.471 |
P1—N3—C8 | 129.16 (14) | H1c11a—C11a—H2c11a | 109.472 |
P1—N3—H1n3 | 115.421 | H1c11a—C11a—H3c11a | 109.47 |
C8—N3—H1n3 | 115.421 | H2c11a—C11a—H3c11a | 109.471 |
P2—N7—C23 | 125.72 (12) | H1c10a—C10a—H2c10a | 109.471 |
P2—N7—H1n7 | 117.14 | H1c10a—C10a—H3c10a | 109.472 |
C23—N7—H1n7 | 117.14 | H1c12a—C12a—H2c12a | 109.471 |
P2—N6—C22 | 122.49 (11) | H1c12a—C12a—H3c12a | 109.471 |
P2—N6—H1n6 | 118.755 | H2c12a—C12a—H3c12a | 109.471 |
C22—N6—H1n6 | 118.755 | H1c11b—C11b—H2c11b | 109.472 |
P1—N4—H1n4 | 115.555 | H1c11b—C11b—H3c11b | 109.47 |
P3—N10—C37 | 122.55 (11) | H2c11b—C11b—H3c11b | 109.471 |
P3—N10—H1n10 | 118.725 | H1c10b—C10b—H2c10b | 109.471 |
C37—N10—H1n10 | 118.725 | H1c10b—C10b—H3c10b | 109.472 |
P1—N2—C7 | 123.35 (12) | H2c10b—C10b—H3c10b | 109.471 |
P1—N2—H1n2 | 118.327 | H1c12b—C12b—H2c12b | 109.471 |
C7—N2—H1n2 | 118.326 | H1c12b—C12b—H3c12b | 109.471 |
N5i—C20—C19 | 117.8 (2) | H2c12b—C12b—H3c12b | 109.471 |
N5i—C20—C21 | 119.17 (16) | C23—C29a—H1c29a | 109.471 |
C19—C20—C21 | 123.0 (2) | C23—C29a—H2c29a | 109.472 |
C17—C18—C19 | 120.96 (17) | C23—C29a—H3c29a | 109.471 |
C17—C18—H1c18 | 119.517 | H1c29a—C29a—H2c29a | 109.471 |
C19—C18—H1c18 | 119.518 | H1c29a—C29a—H3c29a | 109.471 |
P3—N12—H1n12 | 113.923 | H2c29a—C29a—H3c29a | 109.471 |
N12—C39a—C40a | 109.8 (3) | C23—C28a—H1c28a | 109.471 |
N12—C39a—C41a | 109.8 (3) | C23—C28a—H2c28a | 109.471 |
N12—C39a—C42a | 106.8 (3) | C23—C28a—H3c28a | 109.471 |
C40a—C39a—C41a | 109.7 (4) | H1c28a—C28a—H2c28a | 109.471 |
C40a—C39a—C42a | 110.4 (4) | H1c28a—C28a—H3c28a | 109.471 |
C41a—C39a—C42a | 110.4 (4) | H2c28a—C28a—H3c28a | 109.471 |
N12—C39b—C40b | 119.2 (5) | C23—C30a—H1c30a | 109.471 |
N12—C39b—C41b | 92.5 (5) | C23—C30a—H2c30a | 109.471 |
N12—C39b—C42b | 113.2 (6) | C23—C30a—H3c30a | 109.471 |
C40b—C39b—C41b | 109.7 (6) | H1c30a—C30a—H2c30a | 109.472 |
C40b—C39b—C42b | 110.4 (6) | H1c30a—C30a—H3c30a | 109.471 |
C41b—C39b—C42b | 110.4 (5) | H2c30a—C30a—H3c30a | 109.471 |
C4—C3—C2 | 120.89 (18) | C24—C26a—H1c26a | 109.472 |
C4—C3—H1c3 | 119.555 | C24—C26a—H2c26a | 109.471 |
C2—C3—H1c3 | 119.554 | C24—C26a—H3c26a | 109.471 |
N11—C38—C44a | 108.4 (3) | H1c26a—C26a—H2c26a | 109.471 |
N11—C38—C43a | 111.4 (3) | H1c26a—C26a—H3c26a | 109.471 |
N11—C38—C45a | 106.9 (3) | H2c26a—C26a—H3c26a | 109.471 |
N11—C38—C44b | 106.2 (4) | C24—C25a—H1c25a | 109.471 |
N11—C38—C43b | 105.1 (4) | C24—C25a—H2c25a | 109.471 |
N11—C38—C45b | 116.7 (5) | C24—C25a—H3c25a | 109.472 |
C44a—C38—C43a | 109.2 (5) | H1c25a—C25a—H2c25a | 109.472 |
C44a—C38—C45a | 110.5 (4) | H1c25a—C25a—H3c25a | 109.47 |
C43a—C38—C45a | 110.4 (4) | H2c25a—C25a—H3c25a | 109.471 |
C44b—C38—C43b | 106.0 (6) | C24—C27a—H1c27a | 109.471 |
C44b—C38—C45b | 112.1 (6) | C24—C27a—H2c27a | 109.471 |
C43b—C38—C45b | 109.9 (6) | C24—C27a—H3c27a | 109.471 |
C17—C16—C21 | 118.54 (18) | H1c27a—C27a—H2c27a | 109.471 |
C17—C16—C22 | 123.84 (18) | H1c27a—C27a—H3c27a | 109.471 |
C21—C16—C22 | 117.61 (15) | H2c27a—C27a—H3c27a | 109.472 |
C36—C31—C37 | 116.29 (14) | C24—C26b—H1c26b | 108.824 |
C36—C31—C32 | 119.33 (18) | C24—C26b—H2c26b | 107.481 |
C37—C31—C32 | 124.35 (18) | C24—C26b—H3c26b | 112.076 |
N3—C8—C13a | 105.76 (19) | H1c26b—C26b—H2c26b | 109.471 |
N3—C8—C15a | 110.14 (17) | H1c26b—C26b—H3c26b | 109.471 |
N3—C8—C14a | 110.49 (16) | H2c26b—C26b—H3c26b | 109.471 |
C13a—C8—C15a | 109.89 (17) | C24—C25b—H1c25b | 110.425 |
C13a—C8—C14a | 110.2 (2) | C24—C25b—H2c25b | 107.411 |
C15a—C8—C14a | 110.2 (2) | C24—C25b—H3c25b | 110.558 |
N4—C9a—C11a | 107.2 (4) | H1c25b—C25b—H2c25b | 109.472 |
N4—C9a—C10a | 111.7 (5) | H1c25b—C25b—H3c25b | 109.47 |
N4—C9a—C12a | 108.3 (5) | H2c25b—C25b—H3c25b | 109.471 |
C11a—C9a—C10a | 109.1 (6) | C24—C27b—H1c27b | 111.887 |
C11a—C9a—C12a | 110.1 (5) | C24—C27b—H2c27b | 108.129 |
C10a—C9a—C12a | 110.5 (5) | C24—C27b—H3c27b | 108.37 |
N4—C9b—C11b | 104.5 (5) | H1c27b—C27b—H2c27b | 109.471 |
N4—C9b—C10b | 107.9 (5) | H1c27b—C27b—H3c27b | 109.471 |
N4—C9b—C12b | 114.6 (5) | H2c27b—C27b—H3c27b | 109.472 |
C11b—C9b—C10b | 109.1 (6) | C38—C44a—H1c44a | 109.471 |
C11b—C9b—C12b | 110.1 (5) | C38—C44a—H2c44a | 109.471 |
C10b—C9b—C12b | 110.5 (5) | C38—C44a—H3c44a | 109.471 |
C18—C17—C16 | 120.5 (2) | H1c44a—C44a—H2c44a | 109.471 |
C18—C17—H1c17 | 119.741 | H1c44a—C44a—H3c44a | 109.472 |
C16—C17—H1c17 | 119.741 | H2c44a—C44a—H3c44a | 109.47 |
C33—C34—C35 | 118.3 (2) | C38—C43a—H1c43a | 109.472 |
C33—C34—H1c34 | 120.858 | C38—C43a—H2c43a | 109.471 |
C35—C34—H1c34 | 120.859 | C38—C43a—H3c43a | 109.471 |
N8—C24—C26a | 109.6 (2) | H1c43a—C43a—H2c43a | 109.47 |
N8—C24—C25a | 107.1 (3) | H1c43a—C43a—H3c43a | 109.472 |
N8—C24—C27a | 112.9 (3) | H2c43a—C43a—H3c43a | 109.471 |
N8—C24—C26b | 106.8 (3) | C38—C45a—H1c45a | 109.471 |
N8—C24—C25b | 111.9 (3) | C38—C45a—H2c45a | 109.471 |
N8—C24—C27b | 107.5 (4) | C38—C45a—H3c45a | 109.471 |
C26a—C24—C25a | 110.9 (4) | H1c45a—C45a—H2c45a | 109.472 |
C26a—C24—C27a | 105.9 (3) | H1c45a—C45a—H3c45a | 109.471 |
C25a—C24—C27a | 110.5 (4) | H2c45a—C45a—H3c45a | 109.471 |
C26b—C24—C25b | 109.7 (5) | C38—C44b—H1c44b | 110.864 |
C26b—C24—C27b | 110.8 (4) | C38—C44b—H2c44b | 107.324 |
C25b—C24—C27b | 109.9 (4) | C38—C44b—H3c44b | 110.204 |
C20—C19—C18 | 117.6 (2) | H1c44b—C44b—H2c44b | 109.471 |
C20—C19—H1c19 | 121.206 | H1c44b—C44b—H3c44b | 109.472 |
C18—C19—H1c19 | 121.207 | H2c44b—C44b—H3c44b | 109.471 |
C3—C4—C5 | 117.7 (2) | C38—C43b—H1c43b | 108.357 |
C3—C4—H1c4 | 121.148 | C38—C43b—H2c43b | 110.382 |
C5—C4—H1c4 | 121.147 | C38—C43b—H3c43b | 109.668 |
N1—C5—C4 | 118.2 (2) | H1c43b—C43b—H2c43b | 109.47 |
N1—C5—C6 | 119.11 (16) | H1c43b—C43b—H3c43b | 109.472 |
C4—C5—C6 | 122.7 (2) | H2c43b—C43b—H3c43b | 109.471 |
C2—C1—C6 | 118.66 (18) | C38—C45b—H1c45b | 110.846 |
C2—C1—C7 | 124.04 (19) | C38—C45b—H2c45b | 108.074 |
C6—C1—C7 | 117.28 (15) | C38—C45b—H3c45b | 109.482 |
N7—C23—C29a | 110.00 (18) | H1c45b—C45b—H2c45b | 109.472 |
N7—C23—C28a | 106.04 (16) | H1c45b—C45b—H3c45b | 109.471 |
N7—C23—C30a | 111.23 (16) | H2c45b—C45b—H3c45b | 109.471 |
C29a—C23—C28a | 109.70 (18) | H1c40a—C40a—H2c40a | 109.471 |
C29a—C23—C30a | 110.1 (2) | H1c40a—C40a—H3c40a | 109.471 |
C28a—C23—C30a | 109.7 (2) | H2c40a—C40a—H3c40a | 109.471 |
C3—C2—C1 | 120.4 (2) | H1c41a—C41a—H2c41a | 109.471 |
C3—C2—H1c2 | 119.799 | H1c41a—C41a—H3c41a | 109.47 |
C1—C2—H1c2 | 119.799 | H2c41a—C41a—H3c41a | 109.472 |
C5—C6—C1 | 119.65 (16) | H1c42a—C42a—H2c42a | 109.471 |
C5—C6—H1c6 | 120.174 | H1c42a—C42a—H3c42a | 109.471 |
C1—C6—H1c6 | 120.175 | H2c42a—C42a—H3c42a | 109.472 |
C31—C36—C35 | 118.93 (15) | H1c40b—C40b—H2c40b | 109.471 |
C31—C36—H1c36 | 120.536 | H1c40b—C40b—H3c40b | 109.471 |
C35—C36—H1c36 | 120.535 | H2c40b—C40b—H3c40b | 109.471 |
C34—C33—C32 | 120.53 (17) | H1c41b—C41b—H2c41b | 109.471 |
C34—C33—H1c33 | 119.734 | H1c41b—C41b—H3c41b | 109.47 |
C32—C33—H1c33 | 119.733 | H2c41b—C41b—H3c41b | 109.472 |
C20—C21—C16 | 119.39 (16) | H1c42b—C42b—H2c42b | 109.471 |
C20—C21—H1c21 | 120.304 | H1c42b—C42b—H3c42b | 109.471 |
C16—C21—H1c21 | 120.304 | H2c42b—C42b—H3c42b | 109.472 |
Symmetry code: (i) −x+1, −y+1, −z+1. |