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Simplified models for the crystal lattice of the sesquihydrate form of the hemi-sulfate salt of (5S,6S,9R)-5-amino-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-yl 4-(2-oxo-2,3-dihydro-1H-imidazol[4,5b]pyridin-1-yl)-1-piperidine carboxylate (BMS-927711, C28H29F2N6O3+) are used to calculate diffuse diffraction features in order to develop a mechanistic understanding of the dehydration process with respect to disruption of the lattice, since a Bragg model cannot be established. The model demonstrates that what we observe when the water leaves the crystal is partial transformation from the parent form to a child form (a new form, less hydrated and structurally related to the parent). Yet this `dried' structure is not a pure phase. It consists of semi-random layers of both child, parent and an interfacial layer which has a modulated structure that represents a transitory phase. Understanding the fact that a single `dried' crystal can have the disordered layer structure described as well as understanding mechanistic relationships between the phases involved can have implications in understanding the effect of common large scale bulk drying procedures. During the development of BMS-927711, difficulties did arise during characterization of the dried bulk when using only routine solid-state analysis. The material is now better understood from this diffraction study. The diffraction experiments also reveal intermodulation satellites, which upon interpretation yield even more structural information about the crystal transformation. The model suggests the mechanism of transformation is laminar in which layers of the crystal are driven to approach a stable B-centered supercell phase of lower water content.
Supporting information
CCDC reference: 990303
Data collection: Bruker APEX2; cell refinement: Bruker SAINT; data reduction: Bruker SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Bruker SHELXTL; software used to prepare material for publication: Bruker SHELXTL.
BMS-927711–0.5H2SO4 H1.5–1 sesquihydrate CGRP
top
Crystal data top
C28H29F2N6O3+·0.5(O4S2−)·1.5(H2O) | F(000) = 1280 |
Mr = 610.63 | Dx = 1.423 Mg m−3 |
Orthorhombic, P21212 | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: P_2_2ab | Cell parameters from 7294 reflections |
a = 10.9169 (9) Å | θ = 2.7–54.0° |
b = 33.039 (3) Å | µ = 1.27 mm−1 |
c = 7.9038 (6) Å | T = 296 K |
V = 2850.8 (4) Å3 | Prism, colorless |
Z = 4 | 0.26 × 0.22 × 0.18 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 3509 independent reflections |
Radiation source: fine-focus sealed tube | 3235 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
φ and ω scans | θmax = 55.1°, θmin = 2.7° |
Absorption correction: multi-scan SADABS (Sheldrick, 1996) | h = −11→11 |
Tmin = 0.755, Tmax = 0.796 | k = −35→34 |
18471 measured reflections | l = −8→8 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.100 | w = 1/[σ2(Fo2) + (0.056P)2 + 1.0338P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
3509 reflections | Δρmax = 0.39 e Å−3 |
399 parameters | Δρmin = −0.18 e Å−3 |
5 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.01 (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) |
C1 | 0.7702 (3) | 0.86785 (9) | 0.5047 (4) | 0.0448 (8) | |
C2 | 0.7665 (3) | 0.83757 (9) | 0.6299 (4) | 0.0433 (8) | |
C3 | 0.9272 (3) | 0.87905 (9) | 0.6797 (4) | 0.0435 (8) | |
C4 | 0.6025 (4) | 0.84318 (13) | 0.3770 (5) | 0.0699 (11) | |
H4 | 0.5448 | 0.8444 | 0.2906 | 0.084* | |
C5 | 0.5920 (4) | 0.81282 (13) | 0.4927 (5) | 0.0684 (11) | |
H5 | 0.5274 | 0.7946 | 0.4840 | 0.082* | |
C6 | 0.6764 (3) | 0.80866 (11) | 0.6238 (5) | 0.0577 (9) | |
H6 | 0.6720 | 0.7877 | 0.7021 | 0.069* | |
C7 | 0.9084 (3) | 0.82233 (9) | 0.8839 (4) | 0.0456 (8) | |
H7 | 0.9727 | 0.8389 | 0.9355 | 0.055* | |
C8 | 0.9695 (3) | 0.78267 (10) | 0.8327 (5) | 0.0537 (9) | |
H8A | 0.9099 | 0.7650 | 0.7791 | 0.064* | |
H8B | 1.0345 | 0.7880 | 0.7520 | 0.064* | |
C9 | 1.0218 (3) | 0.76215 (11) | 0.9881 (5) | 0.0632 (10) | |
H9A | 1.0543 | 0.7359 | 0.9569 | 0.076* | |
H9B | 1.0887 | 0.7783 | 1.0327 | 0.076* | |
C10 | 0.8686 (4) | 0.79452 (10) | 1.1700 (4) | 0.0581 (9) | |
H10A | 0.9281 | 0.8121 | 1.2238 | 0.070* | |
H10B | 0.8047 | 0.7886 | 1.2517 | 0.070* | |
C11 | 0.8134 (3) | 0.81586 (10) | 1.0190 (4) | 0.0527 (9) | |
H11A | 0.7467 | 0.7998 | 0.9738 | 0.063* | |
H11B | 0.7803 | 0.8418 | 1.0541 | 0.063* | |
C12 | 0.8697 (3) | 0.72181 (9) | 1.1470 (4) | 0.0446 (8) | |
C13 | 0.7480 (3) | 0.68155 (12) | 0.6484 (5) | 0.0633 (10) | |
H13 | 0.7567 | 0.7029 | 0.5727 | 0.076* | |
C14 | 0.6737 (4) | 0.64982 (12) | 0.6034 (5) | 0.0665 (10) | |
H14 | 0.6353 | 0.6493 | 0.4984 | 0.080* | |
C15 | 0.6572 (3) | 0.61860 (11) | 0.7183 (5) | 0.0560 (9) | |
H15 | 0.6064 | 0.5969 | 0.6916 | 0.067* | |
C16 | 0.7163 (3) | 0.61982 (9) | 0.8726 (4) | 0.0450 (8) | |
C17 | 0.7940 (3) | 0.65271 (9) | 0.9039 (4) | 0.0465 (8) | |
C18 | 0.7080 (3) | 0.58701 (9) | 1.0058 (4) | 0.0466 (8) | |
H18 | 0.7040 | 0.6002 | 1.1167 | 0.056* | |
C19 | 0.8201 (3) | 0.55907 (9) | 1.0055 (4) | 0.0482 (8) | |
H19 | 0.8075 | 0.5406 | 0.9102 | 0.058* | |
C20 | 0.9403 (3) | 0.58149 (10) | 0.9660 (5) | 0.0539 (9) | |
H20A | 1.0071 | 0.5626 | 0.9831 | 0.065* | |
H20B | 0.9395 | 0.5884 | 0.8467 | 0.065* | |
C21 | 0.9708 (3) | 0.62003 (10) | 1.0646 (5) | 0.0544 (9) | |
H21A | 1.0450 | 0.6316 | 1.0175 | 0.065* | |
H21B | 0.9882 | 0.6126 | 1.1809 | 0.065* | |
C22 | 0.8709 (3) | 0.65265 (9) | 1.0646 (4) | 0.0467 (8) | |
H22 | 0.8173 | 0.6486 | 1.1626 | 0.056* | |
C23 | 0.8230 (3) | 0.53227 (10) | 1.1619 (4) | 0.0488 (8) | |
C24 | 0.8222 (3) | 0.49037 (11) | 1.1444 (5) | 0.0642 (10) | |
H24 | 0.8191 | 0.4792 | 1.0344 | 0.077* | |
C25 | 0.8278 (3) | 0.46539 (15) | 1.2797 (7) | 0.0846 (14) | |
H25 | 0.8243 | 0.4381 | 1.2622 | 0.101* | |
C26 | 0.8326 (4) | 0.47904 (17) | 1.4381 (7) | 0.0884 (14) | |
H26 | 0.8303 | 0.4613 | 1.5296 | 0.106* | |
C27 | 0.8409 (4) | 0.51975 (18) | 1.4617 (6) | 0.0867 (14) | |
C28 | 0.8331 (4) | 0.54614 (13) | 1.3244 (5) | 0.0716 (12) | |
N1 | 0.8644 (2) | 0.84509 (7) | 0.7370 (3) | 0.0446 (6) | |
N2 | 0.8677 (2) | 0.89196 (7) | 0.5375 (3) | 0.0476 (7) | |
H2 | 0.8891 | 0.9125 | 0.4774 | 0.057* | |
N3 | 0.6912 (3) | 0.87166 (9) | 0.3793 (4) | 0.0600 (8) | |
N4 | 0.9279 (3) | 0.75706 (8) | 1.1190 (4) | 0.0532 (7) | |
N5 | 0.8091 (3) | 0.68348 (8) | 0.7965 (4) | 0.0543 (7) | |
N6 | 0.5959 (2) | 0.56172 (8) | 0.9862 (4) | 0.0534 (7) | |
H6A | 0.6054 | 0.5449 | 0.8992 | 0.080* | |
H6B | 0.5316 | 0.5777 | 0.9675 | 0.080* | |
H6C | 0.5836 | 0.5475 | 1.0803 | 0.080* | |
O1 | 1.0190 (2) | 0.89331 (7) | 0.7438 (3) | 0.0618 (6) | |
O2 | 0.7746 (2) | 0.71789 (7) | 1.2241 (3) | 0.0616 (6) | |
O3 | 0.9356 (2) | 0.69038 (6) | 1.0833 (3) | 0.0509 (6) | |
O4 | 0.3908 (2) | 0.49846 (8) | 0.7592 (3) | 0.0659 (7) | |
O5 | 0.4930 (3) | 0.53644 (7) | 0.5467 (3) | 0.0749 (8) | |
S1 | 0.5000 | 0.5000 | 0.64941 (14) | 0.0455 (3) | |
O1S | 0.5000 | 0.5000 | 0.2134 (5) | 0.0820 (11) | |
H1SA | 0.4864 | 0.5219 | 0.2659 | 0.123* | |
O2S | 0.3401 (3) | 0.57842 (8) | 0.8737 (4) | 0.0800 (8) | |
H2SA | 0.3380 | 0.5533 | 0.8525 | 0.120* | |
H2SB | 0.2905 | 0.5909 | 0.8107 | 0.120* | |
F1 | 0.8437 (3) | 0.58440 (8) | 1.3581 (3) | 0.0868 (11) | 0.817 (5) |
F2 | 0.8604 (4) | 0.53426 (12) | 1.6124 (4) | 0.1079 (13) | 0.817 (5) |
F1A | 0.8206 (8) | 0.4781 (5) | 0.9853 (10) | 0.114 (6)* | 0.183 (5) |
F2A | 0.8316 (9) | 0.4256 (2) | 1.266 (3) | 0.159 (8)* | 0.183 (5) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.045 (2) | 0.0464 (18) | 0.0433 (19) | 0.0033 (15) | 0.0001 (18) | −0.0055 (15) |
C2 | 0.0402 (19) | 0.0449 (17) | 0.0449 (18) | −0.0008 (15) | −0.0003 (17) | −0.0031 (16) |
C3 | 0.046 (2) | 0.0419 (18) | 0.042 (2) | −0.0034 (16) | −0.0003 (17) | −0.0005 (15) |
C4 | 0.054 (2) | 0.093 (3) | 0.063 (3) | −0.010 (2) | −0.020 (2) | 0.004 (2) |
C5 | 0.052 (2) | 0.083 (3) | 0.070 (3) | −0.024 (2) | −0.008 (2) | −0.003 (2) |
C6 | 0.056 (2) | 0.064 (2) | 0.053 (2) | −0.0154 (18) | −0.005 (2) | 0.0046 (17) |
C7 | 0.0461 (19) | 0.0446 (17) | 0.046 (2) | −0.0073 (14) | −0.0118 (17) | 0.0078 (15) |
C8 | 0.050 (2) | 0.054 (2) | 0.057 (2) | −0.0021 (16) | 0.0121 (18) | 0.0117 (17) |
C9 | 0.048 (2) | 0.057 (2) | 0.084 (3) | −0.0025 (17) | 0.005 (2) | 0.020 (2) |
C10 | 0.075 (2) | 0.0475 (19) | 0.052 (2) | −0.0057 (19) | −0.004 (2) | 0.0002 (16) |
C11 | 0.064 (2) | 0.0449 (18) | 0.049 (2) | 0.0024 (16) | 0.0021 (19) | −0.0034 (15) |
C12 | 0.046 (2) | 0.051 (2) | 0.0369 (18) | −0.0023 (17) | −0.0115 (18) | 0.0056 (16) |
C13 | 0.060 (2) | 0.067 (2) | 0.062 (3) | 0.0022 (19) | 0.001 (2) | 0.010 (2) |
C14 | 0.063 (2) | 0.076 (3) | 0.060 (2) | 0.003 (2) | −0.013 (2) | 0.001 (2) |
C15 | 0.049 (2) | 0.058 (2) | 0.061 (2) | −0.0013 (17) | −0.0095 (19) | −0.0097 (19) |
C16 | 0.0386 (17) | 0.0463 (17) | 0.050 (2) | 0.0023 (15) | 0.0017 (17) | −0.0073 (16) |
C17 | 0.0385 (18) | 0.0491 (19) | 0.052 (2) | −0.0004 (15) | 0.0042 (17) | −0.0041 (16) |
C18 | 0.0412 (18) | 0.0478 (17) | 0.051 (2) | −0.0102 (15) | 0.0080 (17) | −0.0130 (15) |
C19 | 0.051 (2) | 0.0475 (18) | 0.0460 (19) | 0.0009 (15) | 0.0094 (17) | −0.0116 (15) |
C20 | 0.0462 (19) | 0.057 (2) | 0.059 (2) | 0.0048 (16) | 0.0067 (18) | 0.0009 (18) |
C21 | 0.0451 (19) | 0.0560 (19) | 0.062 (2) | −0.0024 (16) | 0.0018 (17) | 0.0081 (17) |
C22 | 0.0437 (18) | 0.0449 (18) | 0.052 (2) | −0.0085 (15) | −0.0006 (17) | −0.0011 (15) |
C23 | 0.0395 (18) | 0.058 (2) | 0.049 (2) | −0.0014 (15) | 0.0070 (17) | −0.0001 (17) |
C24 | 0.060 (2) | 0.064 (2) | 0.068 (2) | 0.0067 (18) | 0.006 (2) | 0.018 (2) |
C25 | 0.079 (3) | 0.081 (3) | 0.094 (4) | 0.014 (2) | 0.035 (3) | 0.014 (3) |
C26 | 0.079 (3) | 0.098 (4) | 0.089 (4) | −0.002 (3) | 0.014 (3) | 0.031 (3) |
C27 | 0.084 (3) | 0.133 (4) | 0.044 (3) | −0.037 (3) | 0.004 (2) | −0.002 (3) |
C28 | 0.085 (3) | 0.081 (3) | 0.049 (2) | −0.028 (2) | 0.014 (2) | −0.009 (2) |
N1 | 0.0444 (15) | 0.0418 (14) | 0.0474 (16) | −0.0098 (12) | −0.0088 (15) | 0.0067 (12) |
N2 | 0.0526 (16) | 0.0432 (14) | 0.0469 (16) | −0.0066 (13) | −0.0029 (15) | 0.0051 (12) |
N3 | 0.0532 (18) | 0.074 (2) | 0.0528 (18) | −0.0002 (16) | −0.0116 (17) | 0.0042 (15) |
N4 | 0.0537 (16) | 0.0484 (16) | 0.0575 (18) | −0.0059 (13) | −0.0013 (16) | 0.0124 (14) |
N5 | 0.0511 (17) | 0.0587 (17) | 0.0532 (18) | −0.0016 (14) | −0.0042 (15) | 0.0046 (14) |
N6 | 0.0520 (17) | 0.0488 (15) | 0.0594 (18) | −0.0053 (13) | 0.0091 (15) | −0.0119 (14) |
O1 | 0.0610 (16) | 0.0610 (14) | 0.0633 (15) | −0.0266 (12) | −0.0119 (15) | 0.0071 (12) |
O2 | 0.0555 (15) | 0.0637 (15) | 0.0657 (16) | −0.0076 (12) | 0.0118 (14) | 0.0056 (13) |
O3 | 0.0451 (12) | 0.0477 (12) | 0.0600 (15) | −0.0097 (11) | −0.0033 (11) | 0.0008 (11) |
O4 | 0.0544 (14) | 0.0680 (15) | 0.0752 (16) | 0.0066 (12) | 0.0120 (13) | 0.0230 (15) |
O5 | 0.102 (2) | 0.0499 (13) | 0.0729 (17) | 0.0152 (14) | 0.0111 (18) | 0.0209 (12) |
S1 | 0.0573 (7) | 0.0355 (6) | 0.0436 (6) | −0.0002 (5) | 0.000 | 0.000 |
O1S | 0.106 (3) | 0.079 (2) | 0.061 (2) | −0.004 (2) | 0.000 | 0.000 |
O2S | 0.0904 (19) | 0.0647 (15) | 0.0848 (19) | 0.0085 (14) | −0.0066 (17) | 0.0017 (14) |
F1 | 0.129 (3) | 0.0764 (19) | 0.0553 (16) | −0.0257 (17) | 0.0149 (18) | −0.0219 (14) |
F2 | 0.131 (3) | 0.145 (3) | 0.0477 (18) | −0.045 (2) | 0.0083 (19) | −0.0040 (18) |
Geometric parameters (Å, º) top
C1—N3 | 1.320 (4) | C16—C18 | 1.514 (5) |
C1—N2 | 1.355 (4) | C17—N5 | 1.335 (4) |
C1—C2 | 1.408 (5) | C17—C22 | 1.523 (5) |
C2—C6 | 1.372 (5) | C18—N6 | 1.491 (4) |
C2—N1 | 1.386 (4) | C18—C19 | 1.533 (5) |
C3—O1 | 1.217 (4) | C18—H18 | 0.9800 |
C3—N2 | 1.366 (4) | C19—C23 | 1.521 (5) |
C3—N1 | 1.391 (4) | C19—C20 | 1.539 (5) |
C4—N3 | 1.350 (5) | C19—H19 | 0.9800 |
C4—C5 | 1.362 (6) | C20—C21 | 1.530 (5) |
C4—H4 | 0.9300 | C20—H20A | 0.9700 |
C5—C6 | 1.394 (5) | C20—H20B | 0.9700 |
C5—H5 | 0.9300 | C21—C22 | 1.533 (4) |
C6—H6 | 0.9300 | C21—H21A | 0.9700 |
C7—N1 | 1.464 (4) | C21—H21B | 0.9700 |
C7—C11 | 1.504 (5) | C22—O3 | 1.440 (4) |
C7—C8 | 1.525 (5) | C22—H22 | 0.9800 |
C7—H7 | 0.9800 | C23—C28 | 1.368 (5) |
C8—C9 | 1.515 (5) | C23—C24 | 1.391 (5) |
C8—H8A | 0.9700 | C24—C25 | 1.352 (6) |
C8—H8B | 0.9700 | C24—H24 | 0.9451 |
C9—N4 | 1.466 (5) | C25—C26 | 1.332 (7) |
C9—H9A | 0.9700 | C25—H25 | 0.9133 |
C9—H9B | 0.9700 | C26—C27 | 1.361 (7) |
C10—N4 | 1.454 (4) | C26—H26 | 0.9300 |
C10—C11 | 1.511 (5) | C27—F2 | 1.302 (5) |
C10—H10A | 0.9700 | C27—C28 | 1.395 (6) |
C10—H10B | 0.9700 | C28—F1 | 1.297 (5) |
C11—H11A | 0.9700 | N2—H2 | 0.8600 |
C11—H11B | 0.9700 | N6—H6A | 0.8900 |
C12—O2 | 1.211 (4) | N6—H6B | 0.8900 |
C12—N4 | 1.345 (4) | N6—H6C | 0.8900 |
C12—O3 | 1.360 (4) | O4—S1 | 1.476 (2) |
C13—N5 | 1.349 (5) | O5—S1 | 1.454 (2) |
C13—C14 | 1.372 (5) | S1—O5i | 1.454 (2) |
C13—H13 | 0.9300 | S1—O4i | 1.476 (2) |
C14—C15 | 1.386 (5) | O1S—H1SA | 0.8461 |
C14—H14 | 0.9300 | O2S—H2SA | 0.8481 |
C15—C16 | 1.380 (5) | O2S—H2SB | 0.8439 |
C15—H15 | 0.9300 | F1A—H24 | 0.3905 |
C16—C17 | 1.401 (4) | F2A—H25 | 0.4225 |
| | | |
N3—C1—N2 | 127.0 (3) | C16—C18—H18 | 107.8 |
N3—C1—C2 | 125.2 (3) | C19—C18—H18 | 107.8 |
N2—C1—C2 | 107.8 (3) | C23—C19—C18 | 111.5 (3) |
C6—C2—N1 | 134.4 (3) | C23—C19—C20 | 115.3 (3) |
C6—C2—C1 | 119.4 (3) | C18—C19—C20 | 113.0 (3) |
N1—C2—C1 | 106.2 (3) | C23—C19—H19 | 105.3 |
O1—C3—N2 | 127.8 (3) | C18—C19—H19 | 105.3 |
O1—C3—N1 | 125.6 (3) | C20—C19—H19 | 105.3 |
N2—C3—N1 | 106.6 (3) | C21—C20—C19 | 118.9 (3) |
N3—C4—C5 | 124.4 (4) | C21—C20—H20A | 107.6 |
N3—C4—H4 | 117.8 | C19—C20—H20A | 107.6 |
C5—C4—H4 | 117.8 | C21—C20—H20B | 107.6 |
C4—C5—C6 | 121.1 (3) | C19—C20—H20B | 107.6 |
C4—C5—H5 | 119.5 | H20A—C20—H20B | 107.0 |
C6—C5—H5 | 119.5 | C20—C21—C22 | 115.5 (3) |
C2—C6—C5 | 115.6 (3) | C20—C21—H21A | 108.4 |
C2—C6—H6 | 122.2 | C22—C21—H21A | 108.4 |
C5—C6—H6 | 122.2 | C20—C21—H21B | 108.4 |
N1—C7—C11 | 114.2 (3) | C22—C21—H21B | 108.4 |
N1—C7—C8 | 112.0 (3) | H21A—C21—H21B | 107.5 |
C11—C7—C8 | 111.6 (3) | O3—C22—C17 | 110.8 (3) |
N1—C7—H7 | 106.1 | O3—C22—C21 | 105.0 (2) |
C11—C7—H7 | 106.1 | C17—C22—C21 | 113.1 (3) |
C8—C7—H7 | 106.1 | O3—C22—H22 | 109.3 |
C9—C8—C7 | 109.5 (3) | C17—C22—H22 | 109.3 |
C9—C8—H8A | 109.8 | C21—C22—H22 | 109.3 |
C7—C8—H8A | 109.8 | C28—C23—C24 | 115.3 (4) |
C9—C8—H8B | 109.8 | C28—C23—C19 | 124.7 (3) |
C7—C8—H8B | 109.8 | C24—C23—C19 | 119.9 (3) |
H8A—C8—H8B | 108.2 | C25—C24—C23 | 121.9 (4) |
N4—C9—C8 | 111.1 (3) | C25—C24—H24 | 119.4 |
N4—C9—H9A | 109.4 | C23—C24—H24 | 118.7 |
C8—C9—H9A | 109.4 | C26—C25—C24 | 122.6 (5) |
N4—C9—H9B | 109.4 | C26—C25—H25 | 118.6 |
C8—C9—H9B | 109.4 | C24—C25—H25 | 118.8 |
H9A—C9—H9B | 108.0 | C25—C26—C27 | 117.8 (5) |
N4—C10—C11 | 110.8 (3) | C25—C26—H26 | 121.1 |
N4—C10—H10A | 109.5 | C27—C26—H26 | 121.1 |
C11—C10—H10A | 109.5 | F2—C27—C26 | 120.0 (5) |
N4—C10—H10B | 109.5 | F2—C27—C28 | 119.5 (5) |
C11—C10—H10B | 109.5 | C26—C27—C28 | 120.5 (5) |
H10A—C10—H10B | 108.1 | F1—C28—C23 | 121.8 (4) |
C7—C11—C10 | 110.6 (3) | F1—C28—C27 | 116.3 (4) |
C7—C11—H11A | 109.5 | C23—C28—C27 | 121.7 (4) |
C10—C11—H11A | 109.5 | C2—N1—C3 | 109.0 (3) |
C7—C11—H11B | 109.5 | C2—N1—C7 | 130.2 (2) |
C10—C11—H11B | 109.5 | C3—N1—C7 | 120.7 (3) |
H11A—C11—H11B | 108.1 | C1—N2—C3 | 110.3 (3) |
O2—C12—N4 | 125.5 (3) | C1—N2—H2 | 124.8 |
O2—C12—O3 | 124.0 (3) | C3—N2—H2 | 124.8 |
N4—C12—O3 | 110.5 (3) | C1—N3—C4 | 114.3 (3) |
N5—C13—C14 | 123.6 (4) | C12—N4—C10 | 118.7 (3) |
N5—C13—H13 | 118.2 | C12—N4—C9 | 123.1 (3) |
C14—C13—H13 | 118.2 | C10—N4—C9 | 114.2 (3) |
C13—C14—C15 | 118.4 (4) | C17—N5—C13 | 117.1 (3) |
C13—C14—H14 | 120.8 | C18—N6—H6A | 109.5 |
C15—C14—H14 | 120.8 | C18—N6—H6B | 109.5 |
C16—C15—C14 | 119.7 (3) | H6A—N6—H6B | 109.5 |
C16—C15—H15 | 120.1 | C18—N6—H6C | 109.5 |
C14—C15—H15 | 120.1 | H6A—N6—H6C | 109.5 |
C15—C16—C17 | 117.5 (3) | H6B—N6—H6C | 109.5 |
C15—C16—C18 | 124.5 (3) | C12—O3—C22 | 116.0 (2) |
C17—C16—C18 | 117.9 (3) | O5—S1—O5i | 112.1 (2) |
N5—C17—C16 | 123.6 (3) | O5—S1—O4i | 110.02 (16) |
N5—C17—C22 | 117.6 (3) | O5i—S1—O4i | 108.34 (15) |
C16—C17—C22 | 118.7 (3) | O5—S1—O4 | 108.34 (15) |
N6—C18—C16 | 112.2 (3) | O5i—S1—O4 | 110.02 (16) |
N6—C18—C19 | 108.5 (2) | O4i—S1—O4 | 107.9 (2) |
C16—C18—C19 | 112.5 (3) | H2SA—O2S—H2SB | 110.2 |
N6—C18—H18 | 107.8 | | |
Symmetry code: (i) −x+1, −y+1, z. |
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