#------------------------------------------------------------------------------
#$Date: 2023-08-03 03:00:19 +0300 (Thu, 03 Aug 2023) $
#$Revision: 285432 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/71/7247138.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7247138
loop_
_publ_author_name
'Palica, Katarzyna'
'Deufel, Fritz'
'Skagseth, Susann'
'Di Santo-Meztler, Paula'
'Thoma, Johannes'
'Andersson Rasmussen, Anna'
'Valkonen, Arto'
'Sunnerhagen, Per'
'Leiros, Hanna-Kirsti S.'
'Andersson, Hanna'
'Erdelyi, Mate'
_publ_section_title
;
 α-Aminophosphonate inhibitors of metallo-β-lactamases NDM-1 and VIM-2
;
_journal_name_full               'RSC Medicinal Chemistry'
_journal_paper_doi               10.1039/D3MD00286A
_journal_year                    2023
_chemical_formula_moiety         'C25 H37 N2 O6 P S'
_chemical_formula_sum            'C25 H37 N2 O6 P S'
_chemical_formula_weight         524.59
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-08-26 deposited with the CCDC.	2023-08-01 downloaded from the CCDC.
;
_cell_angle_alpha                86.282(2)
_cell_angle_beta                 87.202(2)
_cell_angle_gamma                79.542(3)
_cell_formula_units_Z            2
_cell_length_a                   9.0460(3)
_cell_length_b                   10.9706(4)
_cell_length_c                   13.8583(3)
_cell_measurement_reflns_used    13016
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.6710
_cell_measurement_theta_min      2.2910
_cell_volume                     1348.64(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    SHELXL-2018/3
_computing_publication_material  SHELXL-2018/3
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 16.0107
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            32817
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.921
_diffrn_reflns_theta_min         2.291
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.947
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         7198
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0493P)²+0.5621P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1105
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6021
_reflns_number_total             7198
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3md00286a2.cif
_cod_data_source_block           4k-1
_cod_database_code               7247138
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.927
_shelx_estimated_absorpt_t_max   0.963
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S13 S 0.80178(7) 0.96653(7) 0.14564(4) 0.02283(19) Uani 0.709(2) 1 d D . P A 1
S13D S 0.83786(19) 0.68363(19) 0.21305(12) 0.0250(4) Uani 0.291(2) 1 d D . P A 2
P1 P 0.35492(4) 0.82432(3) 0.56284(2) 0.02045(9) Uani 1 1 d . . . . .
O1 O 0.37123(12) 0.94104(9) 0.60471(7) 0.0260(2) Uani 1 1 d . . . . .
O10 O 0.52012(14) 0.67173(10) 0.30738(7) 0.0332(3) Uani 1 1 d . . . . .
O1A O 0.22109(11) 0.83856(9) 0.49200(7) 0.0251(2) Uani 1 1 d . . . . .
O1B O 0.32285(12) 0.71601(9) 0.63540(7) 0.0266(2) Uani 1 1 d . . . . .
O4C O 0.72425(14) 0.84095(10) 0.71884(7) 0.0324(3) Uani 1 1 d . . . . .
O5C O 0.67245(12) 0.67213(9) 0.80910(7) 0.0257(2) Uani 1 1 d . . . . .
N4 N 0.65630(14) 0.67862(10) 0.64788(8) 0.0221(2) Uani 1 1 d . . . . .
N9 N 0.53505(13) 0.82628(11) 0.40592(8) 0.0203(2) Uani 1 1 d D . . . .
H9 H 0.5550(18) 0.9022(13) 0.4101(12) 0.024 Uiso 1 1 d D U . . .
C2 C 0.52201(15) 0.75142(12) 0.49589(9) 0.0194(3) Uani 1 1 d . . . . .
H2 H 0.507998 0.666861 0.479646 0.023 Uiso 1 1 calc R U . . .
C3 C 0.66961(16) 0.73850(13) 0.55075(9) 0.0218(3) Uani 1 1 d . . . . .
H3 H 0.690635 0.823753 0.558084 0.026 Uiso 1 1 calc R U . . .
C5 C 0.64524(16) 0.54633(12) 0.65129(10) 0.0236(3) Uani 1 1 d . . . . .
H5A H 0.550646 0.536615 0.622067 0.028 Uiso 1 1 calc R U . . .
H5B H 0.642626 0.513589 0.719506 0.028 Uiso 1 1 calc R U . . .
C6 C 0.77854(17) 0.47270(14) 0.59675(11) 0.0287(3) Uani 1 1 d . . . . .
H6A H 0.764645 0.385448 0.594842 0.034 Uiso 1 1 calc R U . . .
H6B H 0.871795 0.473149 0.631167 0.034 Uiso 1 1 calc R U . . .
C7 C 0.79417(17) 0.52822(14) 0.49340(11) 0.0285(3) Uani 1 1 d . . . . .
H7A H 0.886314 0.483461 0.461077 0.034 Uiso 1 1 calc R U . . .
H7B H 0.706785 0.517976 0.456374 0.034 Uiso 1 1 calc R U . . .
C8 C 0.80262(16) 0.66589(14) 0.49403(10) 0.0261(3) Uani 1 1 d . . . . .
H8A H 0.804245 0.701445 0.426562 0.031 Uiso 1 1 calc R U . . .
H8B H 0.897488 0.674900 0.523255 0.031 Uiso 1 1 calc R U . . .
C10 C 0.53687(15) 0.77784(13) 0.31885(9) 0.0219(3) Uani 1 1 d . . . . .
C11 C 0.56576(16) 0.86621(14) 0.23362(9) 0.0242(3) Uani 1 1 d . . . . .
H11A H 0.502801 0.855548 0.179400 0.029 Uiso 1 1 calc R U . . .
H11B H 0.537479 0.952986 0.252790 0.029 Uiso 1 1 calc R U . . .
C12 C 0.72880(16) 0.84121(13) 0.20119(9) 0.0232(3) Uani 1 1 d D . . . .
C14 C 0.97546(16) 0.86906(14) 0.13133(10) 0.0252(3) Uani 1 1 d D . . . .
C15 C 1.10290(17) 0.90895(15) 0.08963(10) 0.0289(3) Uani 1 1 d . . . . .
H15 H 1.098776 0.992721 0.066049 0.035 Uiso 1 1 calc R U . . .
C16 C 1.23494(18) 0.82431(17) 0.08334(11) 0.0350(4) Uani 1 1 d . . . . .
H16 H 1.322480 0.849886 0.054313 0.042 Uiso 1 1 calc R U . . .
C17 C 1.2422(2) 0.70173(17) 0.11889(12) 0.0393(4) Uani 1 1 d . . . . .
H17 H 1.335021 0.645255 0.114975 0.047 Uiso 1 1 calc R U . . .
C18 C 1.1160(2) 0.66141(16) 0.15976(12) 0.0376(4) Uani 1 1 d . . . . .
H18 H 1.121112 0.577473 0.183165 0.045 Uiso 1 1 calc R U . . .
C19 C 0.98101(18) 0.74558(15) 0.16619(10) 0.0298(3) Uani 1 1 d D . . . .
C20 C 0.8285(3) 0.7390(3) 0.20716(19) 0.0264(6) Uani 0.709(2) 1 d D . P A 1
H20 H 0.804124 0.664006 0.236386 0.032 Uiso 0.709(2) 1 calc R U P A 1
C20D C 0.8219(8) 0.9106(8) 0.1596(5) 0.0394(19) Uani 0.291(2) 1 d D . P A 2
H20D H 0.782635 0.996336 0.147511 0.047 Uiso 0.291(2) 1 calc R U P A 2
C2A C 0.18020(17) 0.95124(13) 0.42956(10) 0.0264(3) Uani 1 1 d . . . . .
H2A1 H 0.271927 0.980047 0.402311 0.032 Uiso 1 1 calc R U . . .
H2A2 H 0.120413 1.018101 0.467160 0.032 Uiso 1 1 calc R U . . .
C3A C 0.0897(2) 0.92055(17) 0.34990(12) 0.0398(4) Uani 1 1 d . . . . .
H3A1 H 0.060641 0.994606 0.306818 0.060 Uiso 1 1 calc R U . . .
H3A2 H 0.149990 0.854527 0.313063 0.060 Uiso 1 1 calc R U . . .
H3A3 H -0.000933 0.892432 0.377660 0.060 Uiso 1 1 calc R U . . .
C2B C 0.2170(2) 0.73362(18) 0.71678(13) 0.0428(4) Uani 1 1 d . . . . .
H2B1 H 0.117463 0.719309 0.698364 0.051 Uiso 1 1 calc R U . . .
H2B2 H 0.205561 0.819745 0.737230 0.051 Uiso 1 1 calc R U . . .
C3B C 0.2739(2) 0.6445(2) 0.79748(14) 0.0582(6) Uani 1 1 d . . . . .
H3B1 H 0.202920 0.655599 0.853265 0.087 Uiso 1 1 calc R U . . .
H3B2 H 0.284304 0.559524 0.776857 0.087 Uiso 1 1 calc R U . . .
H3B3 H 0.372131 0.659651 0.815603 0.087 Uiso 1 1 calc R U . . .
C4C C 0.68854(16) 0.73891(13) 0.72453(10) 0.0227(3) Uani 1 1 d . . . . .
C6C C 0.70514(18) 0.72048(14) 0.90123(10) 0.0272(3) Uani 1 1 d . . . . .
C7C C 0.6610(2) 0.62458(17) 0.97564(11) 0.0400(4) Uani 1 1 d . . . . .
H7C1 H 0.678347 0.647830 1.040679 0.060 Uiso 1 1 calc R U . . .
H7C2 H 0.554235 0.620908 0.970390 0.060 Uiso 1 1 calc R U . . .
H7C3 H 0.721769 0.543055 0.963917 0.060 Uiso 1 1 calc R U . . .
C8C C 0.87203(19) 0.72324(17) 0.90315(12) 0.0368(4) Uani 1 1 d . . . . .
H8C1 H 0.894001 0.755307 0.964241 0.055 Uiso 1 1 calc R U . . .
H8C2 H 0.929357 0.639008 0.897521 0.055 Uiso 1 1 calc R U . . .
H8C3 H 0.900552 0.777200 0.848929 0.055 Uiso 1 1 calc R U . . .
C9C C 0.6089(2) 0.84676(15) 0.91686(11) 0.0348(4) Uani 1 1 d . . . . .
H9C1 H 0.633042 0.876407 0.978389 0.052 Uiso 1 1 calc R U . . .
H9C2 H 0.629291 0.905658 0.863802 0.052 Uiso 1 1 calc R U . . .
H9C3 H 0.502373 0.839703 0.918462 0.052 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 S13 C12 89.13(8) . . ?
C19 S13D C12 85.65(12) . . ?
O1 P1 O1B 116.87(6) . . ?
O1 P1 O1A 113.95(6) . . ?
O1B P1 O1A 102.38(6) . . ?
O1 P1 C2 113.78(6) . . ?
O1B P1 C2 102.15(6) . . ?
O1A P1 C2 106.26(6) . . ?
C2A O1A P1 121.08(9) . . ?
C2B O1B P1 123.36(10) . . ?
C4C O5C C6C 119.89(11) . . ?
C4C N4 C3 118.02(11) . . ?
C4C N4 C5 124.49(11) . . ?
C3 N4 C5 115.73(11) . . ?
C10 N9 C2 121.63(11) . . ?
N9 C2 C3 109.00(11) . . ?
N9 C2 P1 107.64(9) . . ?
C3 C2 P1 114.30(9) . . ?
N4 C3 C8 109.72(11) . . ?
N4 C3 C2 111.63(11) . . ?
C8 C3 C2 111.27(11) . . ?
N4 C5 C6 110.63(12) . . ?
C5 C6 C7 110.87(12) . . ?
C8 C7 C6 110.56(12) . . ?
C7 C8 C3 112.10(12) . . ?
O10 C10 N9 124.14(13) . . ?
O10 C10 C11 121.66(12) . . ?
N9 C10 C11 114.18(12) . . ?
C12 C11 C10 110.46(11) . . ?
C20 C12 C11 130.42(18) . . ?
C20D C12 C11 134.1(4) . . ?
C20 C12 S13 112.87(16) . . ?
C11 C12 S13 116.71(10) . . ?
C20D C12 S13D 105.7(4) . . ?
C11 C12 S13D 120.15(11) . . ?
C15 C14 C19 120.94(14) . . ?
C15 C14 C20D 143.1(4) . . ?
C19 C14 C20D 95.9(4) . . ?
C15 C14 S13 123.44(12) . . ?
C19 C14 S13 115.62(12) . . ?
C16 C15 C14 118.52(15) . . ?
C15 C16 C17 121.03(15) . . ?
C18 C17 C16 120.71(16) . . ?
C17 C18 C19 119.08(15) . . ?
C18 C19 C14 119.71(15) . . ?
C18 C19 C20 134.60(19) . . ?
C14 C19 C20 105.64(19) . . ?
C18 C19 S13D 113.93(14) . . ?
C14 C19 S13D 126.32(15) . . ?
C12 C20 C19 116.7(2) . . ?
C12 C20D C14 126.2(6) . . ?
O1A C2A C3A 107.71(12) . . ?
O1B C2B C3B 108.70(15) . . ?
O4C C4C O5C 124.03(12) . . ?
O4C C4C N4 124.61(13) . . ?
O5C C4C N4 111.34(12) . . ?
O5C C6C C8C 109.32(12) . . ?
O5C C6C C7C 102.47(12) . . ?
C8C C6C C7C 110.94(13) . . ?
O5C C6C C9C 111.32(12) . . ?
C8C C6C C9C 112.29(14) . . ?
C7C C6C C9C 110.08(13) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S13 C14 1.7431(16) . ?
S13 C12 1.7496(15) . ?
S13D C19 1.655(2) . ?
S13D C12 1.830(2) . ?
P1 O1 1.4736(10) . ?
P1 O1B 1.5649(10) . ?
P1 O1A 1.5752(10) . ?
P1 C2 1.8181(14) . ?
O10 C10 1.2221(17) . ?
O1A C2A 1.4630(16) . ?
O1B C2B 1.4426(18) . ?
O4C C4C 1.2170(17) . ?
O5C C4C 1.3572(16) . ?
O5C C6C 1.4768(16) . ?
N4 C4C 1.3573(17) . ?
N4 C3 1.4684(16) . ?
N4 C5 1.4702(17) . ?
N9 C10 1.3479(17) . ?
N9 C2 1.4598(16) . ?
C2 C3 1.5483(18) . ?
C3 C8 1.530(2) . ?
C5 C6 1.521(2) . ?
C6 C7 1.530(2) . ?
C7 C8 1.527(2) . ?
C10 C11 1.5220(18) . ?
C11 C12 1.502(2) . ?
C12 C20 1.306(4) . ?
C12 C20D 1.322(8) . ?
C14 C15 1.393(2) . ?
C14 C19 1.401(2) . ?
C14 C20D 1.426(7) . ?
C15 C16 1.376(2) . ?
C16 C17 1.393(3) . ?
C17 C18 1.381(3) . ?
C18 C19 1.394(2) . ?
C19 C20 1.479(3) . ?
C2A C3A 1.496(2) . ?
C2B C3B 1.484(3) . ?
C6C C8C 1.517(2) . ?
C6C C7C 1.517(2) . ?
C6C C9C 1.519(2) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N9 H9 O1 0.889(13) 1.950(14) 2.8250(15) 167.5(16) 2_676 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 P1 O1A C2A 34.94(12) . . . . ?
O1B P1 O1A C2A 162.08(10) . . . . ?
C2 P1 O1A C2A -91.16(11) . . . . ?
O1 P1 O1B C2B 43.26(15) . . . . ?
O1A P1 O1B C2B -81.99(14) . . . . ?
C2 P1 O1B C2B 168.11(13) . . . . ?
C10 N9 C2 C3 114.10(14) . . . . ?
C10 N9 C2 P1 -121.41(12) . . . . ?
O1 P1 C2 N9 -72.00(10) . . . . ?
O1B P1 C2 N9 161.12(9) . . . . ?
O1A P1 C2 N9 54.20(10) . . . . ?
O1 P1 C2 C3 49.22(11) . . . . ?
O1B P1 C2 C3 -77.65(10) . . . . ?
O1A P1 C2 C3 175.43(9) . . . . ?
C4C N4 C3 C8 110.95(14) . . . . ?
C5 N4 C3 C8 -54.66(15) . . . . ?
C4C N4 C3 C2 -125.23(13) . . . . ?
C5 N4 C3 C2 69.16(15) . . . . ?
N9 C2 C3 N4 172.28(10) . . . . ?
P1 C2 C3 N4 51.80(13) . . . . ?
N9 C2 C3 C8 -64.78(14) . . . . ?
P1 C2 C3 C8 174.75(9) . . . . ?
C4C N4 C5 C6 -108.59(15) . . . . ?
C3 N4 C5 C6 55.96(15) . . . . ?
N4 C5 C6 C7 -54.14(16) . . . . ?
C5 C6 C7 C8 54.42(16) . . . . ?
C6 C7 C8 C3 -54.27(15) . . . . ?
N4 C3 C8 C7 52.88(15) . . . . ?
C2 C3 C8 C7 -71.16(14) . . . . ?
C2 N9 C10 O10 4.0(2) . . . . ?
C2 N9 C10 C11 -174.58(11) . . . . ?
O10 C10 C11 C12 -81.01(17) . . . . ?
N9 C10 C11 C12 97.61(14) . . . . ?
C10 C11 C12 C20 27.8(2) . . . . ?
C10 C11 C12 C20D -150.8(4) . . . . ?
C10 C11 C12 S13 -152.45(10) . . . . ?
C10 C11 C12 S13D 31.61(16) . . . . ?
C14 S13 C12 C20 0.23(16) . . . . ?
C14 S13 C12 C11 -179.56(11) . . . . ?
C19 S13D C12 C20D 2.5(3) . . . . ?
C19 S13D C12 C11 -179.27(11) . . . . ?
C12 S13 C14 C15 -178.75(13) . . . . ?
C12 S13 C14 C19 0.31(11) . . . . ?
C19 C14 C15 C16 0.0(2) . . . . ?
C20D C14 C15 C16 176.3(5) . . . . ?
S13 C14 C15 C16 179.00(11) . . . . ?
C14 C15 C16 C17 -0.8(2) . . . . ?
C15 C16 C17 C18 1.3(2) . . . . ?
C16 C17 C18 C19 -0.8(2) . . . . ?
C17 C18 C19 C14 0.0(2) . . . . ?
C17 C18 C19 C20 -177.3(2) . . . . ?
C17 C18 C19 S13D 177.93(14) . . . . ?
C15 C14 C19 C18 0.4(2) . . . . ?
C20D C14 C19 C18 -177.3(3) . . . . ?
S13 C14 C19 C18 -178.65(11) . . . . ?
C15 C14 C19 C20 178.40(16) . . . . ?
S13 C14 C19 C20 -0.69(18) . . . . ?
C15 C14 C19 S13D -177.23(13) . . . . ?
C20D C14 C19 S13D 5.0(3) . . . . ?
C12 S13D C19 C18 177.27(12) . . . . ?
C12 S13D C19 C14 -4.95(16) . . . . ?
C11 C12 C20 C19 179.05(15) . . . . ?
S13 C12 C20 C19 -0.7(3) . . . . ?
C18 C19 C20 C12 178.41(17) . . . . ?
C14 C19 C20 C12 0.9(3) . . . . ?
C11 C12 C20D C14 -178.3(3) . . . . ?
S13D C12 C20D C14 -0.4(6) . . . . ?
C15 C14 C20D C12 -179.1(3) . . . . ?
C19 C14 C20D C12 -2.3(6) . . . . ?
P1 O1A C2A C3A 160.97(11) . . . . ?
P1 O1B C2B C3B -146.21(15) . . . . ?
C6C O5C C4C O4C -2.6(2) . . . . ?
C6C O5C C4C N4 178.82(12) . . . . ?
C3 N4 C4C O4C 1.9(2) . . . . ?
C5 N4 C4C O4C 166.16(14) . . . . ?
C3 N4 C4C O5C -179.52(11) . . . . ?
C5 N4 C4C O5C -15.29(19) . . . . ?
C4C O5C C6C C8C -66.76(16) . . . . ?
C4C O5C C6C C7C 175.50(13) . . . . ?
C4C O5C C6C C9C 57.87(17) . . . . ?
