#------------------------------------------------------------------------------
#$Date: 2023-08-03 03:00:19 +0300 (Thu, 03 Aug 2023) $
#$Revision: 285432 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/71/7247142.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_7247142
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      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                90
_cell_angle_beta                 107.972(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3831(3)
_cell_length_b                   26.8231(6)
_cell_length_c                   11.5306(3)
_cell_measurement_reflns_used    4841
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.5710
_cell_measurement_theta_min      2.3930
_cell_volume                     2760.47(14)
_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 0.999
_diffrn_measured_fraction_theta_max 0.875
_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  0.0252
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.875
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13222
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.848
_diffrn_reflns_theta_min         2.006
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.948
_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    1.262
_exptl_crystal_description       prism
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         6953
_refine_ls_number_restraints     66
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0464
_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)+(0.0350P)²+1.1442P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1110
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5464
_reflns_number_total             6953
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3md00286a2.cif
_cod_data_source_block           4l-1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7247142
_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   0.921
_shelx_estimated_absorpt_t_max   0.962
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
S14 S 0.10694(7) 0.29621(2) 0.00437(6) 0.03841(19) Uani 0.8923(19) 1 d D . P A 1
S14D S 0.4759(9) 0.3752(3) 0.0351(9) 0.047(2) Uani 0.1077(19) 1 d D U P A 2
P1 P 0.24699(5) 0.53253(2) 0.51530(4) 0.02161(11) Uani 1 1 d . . . . .
O1 O 0.40093(13) 0.54233(5) 0.59353(10) 0.0261(3) Uani 1 1 d . . . . .
O10 O 0.06700(14) 0.42678(5) 0.25746(12) 0.0313(3) Uani 1 1 d . . . . .
O1A O 0.16131(13) 0.49319(5) 0.56955(10) 0.0287(3) Uani 1 1 d . . . . .
O1B O 0.13974(14) 0.57880(5) 0.48547(11) 0.0293(3) Uani 1 1 d . . . . .
O4C O 0.49100(14) 0.62559(5) 0.40327(11) 0.0309(3) Uani 1 1 d . . . . .
O5C O 0.29444(15) 0.67656(4) 0.31271(11) 0.0312(3) Uani 1 1 d . . . . .
N4 N 0.26723(16) 0.59448(5) 0.28594(12) 0.0229(3) Uani 1 1 d . . . . .
N9 N 0.28822(16) 0.45927(5) 0.37323(13) 0.0216(3) Uani 1 1 d D . . . .
H9 H 0.3840(16) 0.4561(7) 0.4014(16) 0.026 Uiso 1 1 d D U . . .
C2 C 0.23382(18) 0.51029(6) 0.36375(14) 0.0203(3) Uani 1 1 d . . . . .
H2 H 0.126056 0.510518 0.312967 0.024 Uiso 1 1 calc R U . . .
C3 C 0.32346(18) 0.54330(6) 0.30039(14) 0.0209(3) Uani 1 1 d . . . . .
H3 H 0.430198 0.544041 0.353496 0.025 Uiso 1 1 calc R U . . .
C5 C 0.1176(2) 0.60183(7) 0.19931(15) 0.0273(4) Uani 1 1 d . . . . .
H5A H 0.092397 0.637771 0.193880 0.033 Uiso 1 1 calc R U . . .
H5B H 0.042797 0.584018 0.228471 0.033 Uiso 1 1 calc R U . . .
C6 C 0.1113(2) 0.58243(7) 0.07377(16) 0.0327(4) Uani 1 1 d . . . . .
H6A H 0.174895 0.603552 0.039364 0.039 Uiso 1 1 calc R U . . .
H6B H 0.007105 0.584356 0.018591 0.039 Uiso 1 1 calc R U . . .
C7 C 0.1658(2) 0.52850(7) 0.08167(15) 0.0305(4) Uani 1 1 d . . . . .
H7A H 0.093696 0.506677 0.104500 0.037 Uiso 1 1 calc R U . . .
H7B H 0.170411 0.517696 0.000802 0.037 Uiso 1 1 calc R U . . .
C8 C 0.3201(2) 0.52301(7) 0.17541(15) 0.0266(4) Uani 1 1 d . . . . .
H8A H 0.394645 0.541160 0.146593 0.032 Uiso 1 1 calc R U . . .
H8B H 0.348579 0.487344 0.183366 0.032 Uiso 1 1 calc R U . . .
C10 C 0.20021(19) 0.42170(6) 0.31289(14) 0.0221(3) Uani 1 1 d . . . . .
C11 C 0.2792(2) 0.37185(6) 0.32025(15) 0.0267(4) Uani 1 1 d D . . . .
H11A H 0.388896 0.376973 0.352038 0.032 Uiso 0.8923(19) 1 calc R U P A 1
H11B H 0.249637 0.349742 0.377666 0.032 Uiso 0.8923(19) 1 calc R U P A 1
H11C H 0.209907 0.344463 0.323762 0.032 Uiso 0.1077(19) 1 calc R U P A 2
H11D H 0.366533 0.370464 0.395002 0.032 Uiso 0.1077(19) 1 calc R U P A 2
C12 C 0.2404(2) 0.34741(7) 0.19769(17) 0.0236(4) Uani 0.8923(19) 1 d D . P A 1
C13 C 0.1267(2) 0.31535(8) 0.1517(2) 0.0322(5) Uani 0.8923(19) 1 d D . P A 1
H13 H 0.062842 0.304204 0.196310 0.039 Uiso 0.8923(19) 1 calc R U P A 1
C15 C 0.2578(3) 0.33278(8) 0.0003(2) 0.0300(5) Uani 0.8923(19) 1 d D . P A 1
C16 C 0.3168(3) 0.33756(8) -0.09661(19) 0.0389(6) Uani 0.8923(19) 1 d . . P A 1
H16 H 0.272523 0.320840 -0.171765 0.047 Uiso 0.8923(19) 1 calc R U P A 1
C17 C 0.4410(3) 0.36722(9) -0.0796(2) 0.0435(6) Uani 0.8923(19) 1 d . . P A 1
H17 H 0.483341 0.370829 -0.144103 0.052 Uiso 0.8923(19) 1 calc R U P A 1
C18 C 0.5067(5) 0.39232(12) 0.0309(4) 0.0356(8) Uani 0.8923(19) 1 d . . P A 1
H18 H 0.593124 0.412332 0.040569 0.043 Uiso 0.8923(19) 1 calc R U P A 1
C19 C 0.4464(3) 0.38808(9) 0.1255(2) 0.0285(5) Uani 0.8923(19) 1 d . . P A 1
H19 H 0.490597 0.405348 0.199841 0.034 Uiso 0.8923(19) 1 calc R U P A 1
C20 C 0.3192(2) 0.35804(7) 0.11120(18) 0.0241(4) Uani 0.8923(19) 1 d D . P A 1
C12D C 0.3341(19) 0.3654(7) 0.2010(13) 0.043(4) Uani 0.1077(19) 1 d D U P A 2
C13D C 0.458(3) 0.3865(9) 0.1782(17) 0.041(4) Uani 0.1077(19) 1 d D U P A 2
H13D H 0.529627 0.405845 0.237553 0.049 Uiso 0.1077(19) 1 calc R U P A 2
C15D C 0.3078(14) 0.3407(6) -0.0036(15) 0.049(4) Uani 0.1077(19) 1 d DG U P A 2
C16D C 0.2364(17) 0.3160(6) -0.1119(12) 0.056(4) Uani 0.1077(19) 1 d G U P A 2
H16D H 0.278533 0.316483 -0.177004 0.067 Uiso 0.1077(19) 1 calc R U P A 2
C17D C 0.1034(16) 0.2905(6) -0.1249(12) 0.060(5) Uani 0.1077(19) 1 d G U P A 2
H17D H 0.054615 0.273567 -0.198942 0.071 Uiso 0.1077(19) 1 calc R U P A 2
C18D C 0.0418(14) 0.2897(5) -0.0297(15) 0.052(4) Uani 0.1077(19) 1 d G U P A 2
H18D H -0.049093 0.272322 -0.038619 0.062 Uiso 0.1077(19) 1 calc R U P A 2
C19D C 0.1132(16) 0.3145(5) 0.0786(12) 0.034(3) Uani 0.1077(19) 1 d G U P A 2
H19D H 0.071118 0.313994 0.143645 0.041 Uiso 0.1077(19) 1 calc R U P A 2
C20D C 0.2462(15) 0.3400(5) 0.0916(12) 0.047(4) Uani 0.1077(19) 1 d DG U P A 2
C2A C 0.2325(2) 0.46083(7) 0.67069(16) 0.0298(4) Uani 1 1 d . . . . .
H2A H 0.332025 0.450582 0.666218 0.036 Uiso 1 1 calc R U . . .
H2B H 0.171099 0.430425 0.665847 0.036 Uiso 1 1 calc R U . . .
C3A C 0.2505(2) 0.48671(8) 0.78920(17) 0.0370(5) Uani 1 1 d . . . . .
H3A H 0.299028 0.464157 0.856714 0.055 Uiso 1 1 calc R U . . .
H3B H 0.312553 0.516531 0.794465 0.055 Uiso 1 1 calc R U . . .
H3C H 0.151858 0.496403 0.794095 0.055 Uiso 1 1 calc R U . . .
C2B C 0.1402(2) 0.61545(7) 0.57801(17) 0.0333(4) Uani 1 1 d . . . . .
H2C H 0.241063 0.630431 0.611433 0.040 Uiso 1 1 calc R U . . .
H2D H 0.112597 0.599643 0.645653 0.040 Uiso 1 1 calc R U . . .
C3B C 0.0277(3) 0.65465(8) 0.5178(2) 0.0474(6) Uani 1 1 d . . . . .
H3D H 0.024742 0.680228 0.577646 0.071 Uiso 1 1 calc R U . . .
H3E H 0.056420 0.669991 0.451085 0.071 Uiso 1 1 calc R U . . .
H3F H -0.071469 0.639341 0.485151 0.071 Uiso 1 1 calc R U . . .
C4C C 0.3624(2) 0.63177(6) 0.33979(14) 0.0236(4) Uani 1 1 d . . . . .
C6C C 0.3778(2) 0.72267(7) 0.35903(17) 0.0326(4) Uani 1 1 d . . . . .
C7C C 0.5152(3) 0.72704(7) 0.31722(18) 0.0397(5) Uani 1 1 d . . . . .
H7C H 0.568675 0.757943 0.349139 0.060 Uiso 1 1 calc R U . . .
H7D H 0.581326 0.698465 0.347532 0.060 Uiso 1 1 calc R U . . .
H7E H 0.484612 0.727528 0.227920 0.060 Uiso 1 1 calc R U . . .
C8C C 0.2640(3) 0.76228(8) 0.2989(2) 0.0519(6) Uani 1 1 d . . . . .
H8C H 0.307226 0.795364 0.323187 0.078 Uiso 1 1 calc R U . . .
H8D H 0.236806 0.758917 0.210096 0.078 Uiso 1 1 calc R U . . .
H8E H 0.174324 0.758191 0.324487 0.078 Uiso 1 1 calc R U . . .
C9C C 0.4167(3) 0.72470(8) 0.49667(18) 0.0471(6) Uani 1 1 d . . . . .
H9C H 0.472091 0.755437 0.526979 0.071 Uiso 1 1 calc R U . . .
H9D H 0.324317 0.724130 0.519456 0.071 Uiso 1 1 calc R U . . .
H9E H 0.478663 0.695839 0.532559 0.071 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
C13 S14 C15 91.03(11) . . ?
C13D S14D C15D 89.6(10) . . ?
O1 P1 O1B 115.80(7) . . ?
O1 P1 O1A 113.75(7) . . ?
O1B P1 O1A 104.29(7) . . ?
O1 P1 C2 114.29(7) . . ?
O1B P1 C2 101.57(7) . . ?
O1A P1 C2 105.78(7) . . ?
C2A O1A P1 124.12(11) . . ?
C2B O1B P1 121.28(11) . . ?
C4C O5C C6C 120.20(14) . . ?
C4C N4 C3 118.47(14) . . ?
C4C N4 C5 124.77(15) . . ?
C3 N4 C5 116.15(13) . . ?
C10 N9 C2 121.26(14) . . ?
N9 C2 C3 110.14(13) . . ?
N9 C2 P1 108.62(11) . . ?
C3 C2 P1 112.36(11) . . ?
N4 C3 C8 108.94(13) . . ?
N4 C3 C2 111.15(13) . . ?
C8 C3 C2 112.57(13) . . ?
N4 C5 C6 110.53(15) . . ?
C5 C6 C7 110.68(14) . . ?
C8 C7 C6 111.18(15) . . ?
C7 C8 C3 111.87(14) . . ?
O10 C10 N9 123.32(16) . . ?
O10 C10 C11 121.99(15) . . ?
N9 C10 C11 114.69(15) . . ?
C12 C11 C10 111.13(14) . . ?
C10 C11 C12D 108.9(7) . . ?
C13 C12 C20 111.57(18) . . ?
C13 C12 C11 125.72(19) . . ?
C20 C12 C11 122.64(17) . . ?
C12 C13 S14 114.10(17) . . ?
C16 C15 C20 122.1(2) . . ?
C16 C15 S14 126.99(18) . . ?
C20 C15 S14 110.92(17) . . ?
C17 C16 C15 117.8(2) . . ?
C16 C17 C18 121.5(2) . . ?
C19 C18 C17 120.4(3) . . ?
C18 C19 C20 119.7(3) . . ?
C15 C20 C19 118.5(2) . . ?
C15 C20 C12 112.38(19) . . ?
C19 C20 C12 129.06(19) . . ?
C13D C12D C20D 108.2(14) . . ?
C13D C12D C11 128.4(13) . . ?
C20D C12D C11 123.0(13) . . ?
C12D C13D S14D 116.1(15) . . ?
C16D C15D C20D 120.0 . . ?
C16D C15D S14D 128.6(10) . . ?
C20D C15D S14D 111.4(10) . . ?
C15D C16D C17D 120.0 . . ?
C16D C17D C18D 120.0 . . ?
C19D C18D C17D 120.0 . . ?
C20D C19D C18D 120.0 . . ?
C19D C20D C15D 120.0 . . ?
C19D C20D C12D 125.3(12) . . ?
C15D C20D C12D 114.7(12) . . ?
O1A C2A C3A 110.69(16) . . ?
O1B C2B C3B 107.00(15) . . ?
O4C C4C O5C 124.84(16) . . ?
O4C C4C N4 124.51(16) . . ?
O5C C4C N4 110.65(15) . . ?
O5C C6C C7C 111.03(15) . . ?
O5C C6C C8C 101.68(16) . . ?
C7C C6C C8C 110.45(17) . . ?
O5C C6C C9C 109.82(15) . . ?
C7C C6C C9C 112.17(18) . . ?
C8C C6C C9C 111.22(17) . . ?
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
S14 C13 1.729(2) . ?
S14 C15 1.735(3) . ?
S14D C13D 1.733(16) . ?
S14D C15D 1.763(11) . ?
P1 O1 1.4714(12) . ?
P1 O1B 1.5678(13) . ?
P1 O1A 1.5689(13) . ?
P1 C2 1.8142(16) . ?
O10 C10 1.223(2) . ?
O1A C2A 1.442(2) . ?
O1B C2B 1.450(2) . ?
O4C C4C 1.214(2) . ?
O5C C4C 1.351(2) . ?
O5C C6C 1.473(2) . ?
N4 C4C 1.357(2) . ?
N4 C3 1.462(2) . ?
N4 C5 1.464(2) . ?
N9 C10 1.352(2) . ?
N9 C2 1.453(2) . ?
C2 C3 1.551(2) . ?
C3 C8 1.532(2) . ?
C5 C6 1.522(2) . ?
C6 C7 1.527(3) . ?
C7 C8 1.523(3) . ?
C10 C11 1.518(2) . ?
C11 C12 1.497(2) . ?
C11 C12D 1.620(14) . ?
C12 C13 1.345(3) . ?
C12 C20 1.441(3) . ?
C15 C16 1.397(3) . ?
C15 C20 1.404(3) . ?
C16 C17 1.374(4) . ?
C17 C18 1.405(5) . ?
C18 C19 1.379(4) . ?
C19 C20 1.407(3) . ?
C12D C13D 1.393(17) . ?
C12D C20D 1.447(15) . ?
C15D C16D 1.3900 . ?
C15D C20D 1.3900 . ?
C16D C17D 1.3900 . ?
C17D C18D 1.3900 . ?
C18D C19D 1.3900 . ?
C19D C20D 1.3900 . ?
C2A C3A 1.495(3) . ?
C2B C3B 1.500(3) . ?
C6C C7C 1.514(3) . ?
C6C C8C 1.514(3) . ?
C6C C9C 1.516(3) . ?
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 0.860(14) 2.001(15) 2.8225(18) 159.4(17) 3_666 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 -13.70(15) . . . . ?
O1B P1 O1A C2A -140.77(13) . . . . ?
C2 P1 O1A C2A 112.55(13) . . . . ?
O1 P1 O1B C2B -41.31(15) . . . . ?
O1A P1 O1B C2B 84.47(14) . . . . ?
C2 P1 O1B C2B -165.75(13) . . . . ?
C10 N9 C2 C3 -114.96(16) . . . . ?
C10 N9 C2 P1 121.60(14) . . . . ?
O1 P1 C2 N9 72.15(13) . . . . ?
O1B P1 C2 N9 -162.41(11) . . . . ?
O1A P1 C2 N9 -53.77(12) . . . . ?
O1 P1 C2 C3 -49.95(14) . . . . ?
O1B P1 C2 C3 75.49(12) . . . . ?
O1A P1 C2 C3 -175.87(11) . . . . ?
C4C N4 C3 C8 -115.45(16) . . . . ?
C5 N4 C3 C8 56.03(18) . . . . ?
C4C N4 C3 C2 119.96(15) . . . . ?
C5 N4 C3 C2 -68.56(17) . . . . ?
N9 C2 C3 N4 178.01(12) . . . . ?
P1 C2 C3 N4 -60.76(15) . . . . ?
N9 C2 C3 C8 55.49(18) . . . . ?
P1 C2 C3 C8 176.73(11) . . . . ?
C4C N4 C5 C6 114.10(18) . . . . ?
C3 N4 C5 C6 -56.78(19) . . . . ?
N4 C5 C6 C7 53.2(2) . . . . ?
C5 C6 C7 C8 -53.5(2) . . . . ?
C6 C7 C8 C3 54.3(2) . . . . ?
N4 C3 C8 C7 -53.41(19) . . . . ?
C2 C3 C8 C7 70.34(19) . . . . ?
C2 N9 C10 O10 -7.7(2) . . . . ?
C2 N9 C10 C11 173.08(14) . . . . ?
O10 C10 C11 C12 46.3(2) . . . . ?
N9 C10 C11 C12 -134.46(16) . . . . ?
O10 C10 C11 C12D 85.6(7) . . . . ?
N9 C10 C11 C12D -95.2(7) . . . . ?
C10 C11 C12 C13 -91.2(2) . . . . ?
C10 C11 C12 C20 85.5(2) . . . . ?
C20 C12 C13 S14 -0.1(2) . . . . ?
C11 C12 C13 S14 177.00(15) . . . . ?
C15 S14 C13 C12 -0.26(18) . . . . ?
C13 S14 C15 C16 179.7(2) . . . . ?
C13 S14 C15 C20 0.51(17) . . . . ?
C20 C15 C16 C17 1.5(3) . . . . ?
S14 C15 C16 C17 -177.60(19) . . . . ?
C15 C16 C17 C18 -0.4(4) . . . . ?
C16 C17 C18 C19 -0.6(5) . . . . ?
C17 C18 C19 C20 0.6(5) . . . . ?
C16 C15 C20 C19 -1.6(3) . . . . ?
S14 C15 C20 C19 177.67(17) . . . . ?
C16 C15 C20 C12 -179.9(2) . . . . ?
S14 C15 C20 C12 -0.6(2) . . . . ?
C18 C19 C20 C15 0.5(4) . . . . ?
C18 C19 C20 C12 178.5(3) . . . . ?
C13 C12 C20 C15 0.5(3) . . . . ?
C11 C12 C20 C15 -176.70(18) . . . . ?
C13 C12 C20 C19 -177.6(2) . . . . ?
C11 C12 C20 C19 5.2(3) . . . . ?
C10 C11 C12D C13D 79(2) . . . . ?
C10 C11 C12D C20D -93.8(15) . . . . ?
C20D C12D C13D S14D -2(2) . . . . ?
C11 C12D C13D S14D -175.3(13) . . . . ?
C15D S14D C13D C12D 0.7(19) . . . . ?
C13D S14D C15D C16D -179.0(13) . . . . ?
C13D S14D C15D C20D 0.9(12) . . . . ?
C20D C15D C16D C17D 0.0 . . . . ?
S14D C15D C16D C17D 179.8(15) . . . . ?
C15D C16D C17D C18D 0.0 . . . . ?
C16D C17D C18D C19D 0.0 . . . . ?
C17D C18D C19D C20D 0.0 . . . . ?
C18D C19D C20D C15D 0.0 . . . . ?
C18D C19D C20D C12D -177.4(16) . . . . ?
C16D C15D C20D C19D 0.0 . . . . ?
S14D C15D C20D C19D -179.9(13) . . . . ?
C16D C15D C20D C12D 177.6(14) . . . . ?
S14D C15D C20D C12D -2.2(13) . . . . ?
C13D C12D C20D C19D -179.8(15) . . . . ?
C11 C12D C20D C19D -6(2) . . . . ?
C13D C12D C20D C15D 3(2) . . . . ?
C11 C12D C20D C15D 176.4(11) . . . . ?
P1 O1A C2A C3A 84.55(17) . . . . ?
P1 O1B C2B C3B 178.75(14) . . . . ?
C6C O5C C4C O4C 1.3(2) . . . . ?
C6C O5C C4C N4 -178.53(14) . . . . ?
C3 N4 C4C O4C -2.6(2) . . . . ?
C5 N4 C4C O4C -173.30(16) . . . . ?
C3 N4 C4C O5C 177.22(13) . . . . ?
C5 N4 C4C O5C 6.5(2) . . . . ?
C4C O5C C6C C7C 58.2(2) . . . . ?
C4C O5C C6C C8C 175.65(16) . . . . ?
C4C O5C C6C C9C -66.5(2) . . . . ?
