#------------------------------------------------------------------------------
#$Date: 2023-08-03 03:00:19 +0300 (Thu, 03 Aug 2023) $
#$Revision: 285432 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/71/7247135.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_7247135
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         'C21 H35 N2 O6 P S'
_chemical_formula_sum            'C21 H35 N2 O6 P S'
_chemical_formula_weight         474.54
_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
_atom_sites_solution_primary     iterative
_audit_creation_method           SHELXL-2019/2
_audit_update_record
;
2023-03-07 deposited with the CCDC.	2023-08-01 downloaded from the CCDC.
;
_cell_angle_alpha                103.022(5)
_cell_angle_beta                 100.213(5)
_cell_angle_gamma                102.017(6)
_cell_formula_units_Z            2
_cell_length_a                   9.2861(6)
_cell_length_b                   11.2061(9)
_cell_length_c                   12.3620(6)
_cell_measurement_reflns_used    5547
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.7450
_cell_measurement_theta_min      2.9220
_cell_volume                     1191.44(15)
_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-2019/2
_computing_publication_material  SHELXL-2019/2
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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 0.904
_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  0.0728
_diffrn_reflns_av_unetI/netI     0.0649
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18917
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.949
_diffrn_reflns_theta_min         2.219
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.629
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       'stacked plate'
_exptl_crystal_F_000             508
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.812
_refine_diff_density_min         -0.853
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         6250
_refine_ls_number_restraints     128
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0702
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1179P)²+0.1893P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1820
_refine_ls_wR_factor_ref         0.2123
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4561
_reflns_number_total             6250
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3md00286a2.cif
_cod_data_source_block           4i-1
_cod_original_cell_volume        1191.44(14)
_cod_database_code               7247135
_shelx_shelxl_version_number     2019/2
_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   0.935
_shelx_estimated_absorpt_t_max   0.972
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 0.7748(3) 0.4536(3) 0.02835(16) 0.0312(4) Uani 0.612(3) 1 d D U P A 1
S13B S 0.8157(5) 0.4038(5) 0.2474(3) 0.0327(7) Uani 0.388(3) 1 d D U P A 2
P1 P 0.46607(7) 0.72096(6) 0.52148(5) 0.03078(19) Uani 1 1 d D . . . .
O1 O 0.39751(19) 0.61204(17) 0.55893(14) 0.0377(4) Uani 1 1 d . . . . .
O10 O 0.70682(19) 0.74915(15) 0.27711(13) 0.0339(4) Uani 1 1 d . . . . .
O1A O 0.36003(18) 0.74058(15) 0.41586(13) 0.0334(4) Uani 1 1 d . . . . .
O1B O 0.5221(4) 0.8595(3) 0.6084(3) 0.0343(7) Uani 0.781(7) 1 d D . P B 1
O1D O 0.4675(14) 0.8325(10) 0.6206(8) 0.028(2) Uani 0.219(7) 1 d D . P B 2
O4C O 0.68482(19) 0.66814(15) 0.77294(13) 0.0347(4) Uani 1 1 d . . . . .
O5C O 0.78070(17) 0.88031(14) 0.85753(12) 0.0286(3) Uani 1 1 d . . . . .
N4 N 0.8031(2) 0.79878(18) 0.68042(15) 0.0304(4) Uani 1 1 d . . . . .
N9 N 0.6086(2) 0.61660(18) 0.37464(15) 0.0289(4) Uani 1 1 d D . . . .
H9 H 0.575(3) 0.5373(17) 0.376(2) 0.031(6) Uiso 1 1 d D . . . .
C2 C 0.6441(3) 0.7156(2) 0.48111(17) 0.0292(5) Uani 1 1 d . . . . .
H2 H 0.685770 0.798261 0.465692 0.035 Uiso 1 1 calc R U . . .
C3 C 0.7662(3) 0.6958(2) 0.57416(17) 0.0304(5) Uani 1 1 d . . . . .
H3 H 0.725108 0.613880 0.590912 0.037 Uiso 1 1 calc R U . . .
C5 C 0.8868(3) 0.9238(2) 0.67905(19) 0.0325(5) Uani 1 1 d . . . . .
H5A H 0.910865 0.983106 0.756300 0.039 Uiso 1 1 calc R U . . .
H5B H 0.823704 0.956987 0.625732 0.039 Uiso 1 1 calc R U . . .
C6 C 1.0329(3) 0.9152(3) 0.6416(2) 0.0391(6) Uani 1 1 d . . . . .
H6A H 1.101349 0.892683 0.700283 0.047 Uiso 1 1 calc R U . . .
H6B H 1.084562 0.998856 0.634588 0.047 Uiso 1 1 calc R U . . .
C7 C 1.0006(3) 0.8158(3) 0.5272(2) 0.0423(6) Uani 1 1 d . . . . .
H7A H 0.942684 0.843565 0.466593 0.051 Uiso 1 1 calc R U . . .
H7B H 1.097496 0.807199 0.507580 0.051 Uiso 1 1 calc R U . . .
C8 C 0.9113(3) 0.6890(3) 0.53254(19) 0.0382(6) Uani 1 1 d . . . . .
H8A H 0.976140 0.655654 0.584516 0.046 Uiso 1 1 calc R U . . .
H8B H 0.883826 0.628655 0.455556 0.046 Uiso 1 1 calc R U . . .
C10 C 0.6439(2) 0.6432(2) 0.27949(18) 0.0276(4) Uani 1 1 d . . . . .
C11 C 0.5958(2) 0.5303(2) 0.17383(18) 0.0306(5) Uani 1 1 d . . . . .
H11A H 0.509870 0.466803 0.182223 0.037 Uiso 1 1 calc R U . . .
H11B H 0.559757 0.559044 0.106265 0.037 Uiso 1 1 calc R U . . .
C12 C 0.7202(2) 0.4683(2) 0.15326(17) 0.0284(4) Uani 1 1 d D U . . .
C14 C 0.9006(14) 0.3702(10) 0.0680(9) 0.0299(14) Uani 0.612(3) 1 d D U P A 1
H14 H 0.963062 0.338603 0.021641 0.036 Uiso 0.612(3) 1 calc R U P A 1
C15 C 0.9000(9) 0.3546(10) 0.1746(7) 0.0329(13) Uani 0.612(3) 1 d D U P A 1
H15 H 0.961775 0.310885 0.211555 0.039 Uiso 0.612(3) 1 calc R U P A 1
C16 C 0.7943(14) 0.4126(12) 0.2230(9) 0.041(2) Uani 0.612(3) 1 d D U P A 1
H16 H 0.777935 0.412031 0.296580 0.049 Uiso 0.612(3) 1 calc R U P A 1
C14B C 0.9296(14) 0.3603(16) 0.1576(11) 0.0317(19) Uani 0.388(3) 1 d D U P A 2
H14B H 1.008416 0.321121 0.176490 0.038 Uiso 0.388(3) 1 calc R U P A 2
C15B C 0.893(2) 0.3889(17) 0.0559(15) 0.035(2) Uani 0.388(3) 1 d D U P A 2
H15B H 0.942422 0.371890 -0.004711 0.042 Uiso 0.388(3) 1 calc R U P A 2
C16B C 0.771(2) 0.4476(17) 0.0535(10) 0.035(3) Uani 0.388(3) 1 d D U P A 2
H16B H 0.726983 0.470636 -0.011743 0.042 Uiso 0.388(3) 1 calc R U P A 2
C2A C 0.2335(3) 0.6389(2) 0.3395(2) 0.0379(5) Uani 1 1 d . . . . .
H2A H 0.168088 0.600436 0.384322 0.045 Uiso 1 1 calc R U . . .
H2B H 0.271880 0.572043 0.295570 0.045 Uiso 1 1 calc R U . . .
C3A C 0.1453(3) 0.6943(3) 0.2603(2) 0.0419(6) Uani 1 1 d . . . . .
H3A H 0.059664 0.627549 0.208170 0.063 Uiso 1 1 calc R U . . .
H3B H 0.107372 0.760065 0.304473 0.063 Uiso 1 1 calc R U . . .
H3C H 0.210797 0.731773 0.216036 0.063 Uiso 1 1 calc R U . . .
C2B C 0.4138(3) 0.9167(3) 0.6589(3) 0.0353(9) Uani 0.781(7) 1 d D . P B 1
H2C H 0.366704 0.864588 0.704595 0.042 Uiso 0.781(7) 1 calc R U P B 1
H2D H 0.332814 0.923730 0.598606 0.042 Uiso 0.781(7) 1 calc R U P B 1
C3B C 0.5010(3) 1.0448(2) 0.7333(2) 0.0373(5) Uani 1 1 d D . . . .
H3D H 0.432712 1.087332 0.769493 0.056 Uiso 0.781(7) 1 calc R U P B 1
H3E H 0.580745 1.036210 0.792411 0.056 Uiso 0.781(7) 1 calc R U P B 1
H3F H 0.547025 1.095056 0.686954 0.056 Uiso 0.781(7) 1 calc R U P B 1
H3G H 0.508365 1.132471 0.730427 0.056 Uiso 0.219(7) 1 calc R U P B 2
H3H H 0.415037 1.015726 0.765212 0.056 Uiso 0.219(7) 1 calc R U P B 2
H3I H 0.594627 1.040554 0.781642 0.056 Uiso 0.219(7) 1 calc R U P B 2
C2D C 0.4776(12) 0.9594(8) 0.6120(7) 0.027(3) Uani 0.219(7) 1 d D . P B 2
H2E H 0.383375 0.963022 0.562255 0.032 Uiso 0.219(7) 1 calc R U P B 2
H2F H 0.563716 0.987954 0.578754 0.032 Uiso 0.219(7) 1 calc R U P B 2
C4C C 0.7497(2) 0.7732(2) 0.77094(17) 0.0278(4) Uani 1 1 d . . . . .
C6C C 0.7328(3) 0.8769(2) 0.96494(17) 0.0294(5) Uani 1 1 d . . . . .
C7C C 0.8104(3) 0.7948(3) 1.0240(2) 0.0379(5) Uani 1 1 d . . . . .
H7C H 0.777723 0.793245 1.094968 0.057 Uiso 1 1 calc R U . . .
H7D H 0.783155 0.708307 0.973655 0.057 Uiso 1 1 calc R U . . .
H7E H 0.920383 0.829558 1.041649 0.057 Uiso 1 1 calc R U . . .
C8C C 0.7897(3) 1.0149(2) 1.03399(19) 0.0347(5) Uani 1 1 d . . . . .
H8C H 0.763855 1.024294 1.108423 0.052 Uiso 1 1 calc R U . . .
H8D H 0.899897 1.042364 1.045264 0.052 Uiso 1 1 calc R U . . .
H8E H 0.742025 1.067220 0.992857 0.052 Uiso 1 1 calc R U . . .
C9C C 0.5614(3) 0.8335(2) 0.9406(2) 0.0359(5) Uani 1 1 d . . . . .
H9C H 0.530435 0.831442 1.012017 0.054 Uiso 1 1 calc R U . . .
H9D H 0.517189 0.892660 0.906715 0.054 Uiso 1 1 calc R U . . .
H9E H 0.526016 0.748505 0.887219 0.054 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
C12 S13 C14 91.9(4) . . ?
C12 S13B C14B 92.9(6) . . ?
O1 P1 O1D 101.6(5) . . ?
O1 P1 O1A 113.35(10) . . ?
O1D P1 O1A 103.3(4) . . ?
O1 P1 O1B 120.28(15) . . ?
O1A P1 O1B 103.03(14) . . ?
O1 P1 C2 114.91(10) . . ?
O1D P1 C2 117.6(5) . . ?
O1A P1 C2 105.68(9) . . ?
O1B P1 C2 97.45(14) . . ?
C2A O1A P1 122.40(15) . . ?
C2B O1B P1 119.9(3) . . ?
C2D O1D P1 124.1(8) . . ?
C4C O5C C6C 120.82(17) . . ?
C4C N4 C5 124.41(18) . . ?
C4C N4 C3 118.25(19) . . ?
C5 N4 C3 117.23(17) . . ?
C10 N9 C2 120.83(19) . . ?
C10 N9 H9 120.7(17) . . ?
C2 N9 H9 118.0(17) . . ?
N9 C2 C3 111.87(17) . . ?
N9 C2 P1 106.97(15) . . ?
C3 C2 P1 114.20(14) . . ?
N9 C2 H2 107.9 . . ?
C3 C2 H2 107.9 . . ?
P1 C2 H2 107.9 . . ?
N4 C3 C8 109.34(19) . . ?
N4 C3 C2 110.97(17) . . ?
C8 C3 C2 111.03(17) . . ?
N4 C3 H3 108.5 . . ?
C8 C3 H3 108.5 . . ?
C2 C3 H3 108.5 . . ?
N4 C5 C6 110.04(19) . . ?
N4 C5 H5A 109.7 . . ?
C6 C5 H5A 109.7 . . ?
N4 C5 H5B 109.7 . . ?
C6 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
C5 C6 C7 111.0(2) . . ?
C5 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 C6 110.7(2) . . ?
C8 C7 H7A 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C7 C8 C3 113.2(2) . . ?
C7 C8 H8A 108.9 . . ?
C3 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
C3 C8 H8B 108.9 . . ?
H8A C8 H8B 107.8 . . ?
O10 C10 N9 123.2(2) . . ?
O10 C10 C11 122.09(19) . . ?
N9 C10 C11 114.7(2) . . ?
C12 C11 C10 113.38(18) . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C16 C12 C11 126.9(6) . . ?
C16B C12 C11 125.6(7) . . ?
C16 C12 S13 112.3(5) . . ?
C11 C12 S13 120.69(18) . . ?
C16B C12 S13B 109.2(7) . . ?
C11 C12 S13B 125.1(2) . . ?
C15 C14 S13 111.8(10) . . ?
C15 C14 H14 124.1 . . ?
S13 C14 H14 124.1 . . ?
C14 C15 C16 111.1(10) . . ?
C14 C15 H15 124.4 . . ?
C16 C15 H15 124.4 . . ?
C12 C16 C15 113.0(9) . . ?
C12 C16 H16 123.5 . . ?
C15 C16 H16 123.5 . . ?
C15B C14B S13B 112.0(16) . . ?
C15B C14B H14B 124.0 . . ?
S13B C14B H14B 124.0 . . ?
C14B C15B C16B 110.7(18) . . ?
C14B C15B H15B 124.6 . . ?
C16B C15B H15B 124.6 . . ?
C12 C16B C15B 114.9(13) . . ?
C12 C16B H16B 122.5 . . ?
C15B C16B H16B 122.5 . . ?
O1A C2A C3A 108.1(2) . . ?
O1A C2A H2A 110.1 . . ?
C3A C2A H2A 110.1 . . ?
O1A C2A H2B 110.1 . . ?
C3A C2A H2B 110.1 . . ?
H2A C2A H2B 108.4 . . ?
C2A C3A H3A 109.5 . . ?
C2A C3A H3B 109.5 . . ?
H3A C3A H3B 109.5 . . ?
C2A C3A H3C 109.5 . . ?
H3A C3A H3C 109.5 . . ?
H3B C3A H3C 109.5 . . ?
O1B C2B C3B 106.4(3) . . ?
O1B C2B H2C 110.5 . . ?
C3B C2B H2C 110.5 . . ?
O1B C2B H2D 110.5 . . ?
C3B C2B H2D 110.5 . . ?
H2C C2B H2D 108.6 . . ?
C2B C3B H3D 109.5 . . ?
C2B C3B H3E 109.5 . . ?
H3D C3B H3E 109.5 . . ?
C2B C3B H3F 109.5 . . ?
H3D C3B H3F 109.5 . . ?
H3E C3B H3F 109.5 . . ?
C2D C3B H3G 109.5 . . ?
C2D C3B H3H 109.5 . . ?
H3G C3B H3H 109.5 . . ?
C2D C3B H3I 109.5 . . ?
H3G C3B H3I 109.5 . . ?
H3H C3B H3I 109.5 . . ?
O1D C2D C3B 107.4(7) . . ?
O1D C2D H2E 110.2 . . ?
C3B C2D H2E 110.2 . . ?
O1D C2D H2F 110.2 . . ?
C3B C2D H2F 110.2 . . ?
H2E C2D H2F 108.5 . . ?
O4C C4C O5C 125.22(19) . . ?
O4C C4C N4 124.02(19) . . ?
O5C C4C N4 110.75(19) . . ?
O5C C6C C7C 110.26(17) . . ?
O5C C6C C9C 109.86(18) . . ?
C7C C6C C9C 112.8(2) . . ?
O5C C6C C8C 102.18(17) . . ?
C7C C6C C8C 110.5(2) . . ?
C9C C6C C8C 110.73(18) . . ?
C6C C7C H7C 109.5 . . ?
C6C C7C H7D 109.5 . . ?
H7C C7C H7D 109.5 . . ?
C6C C7C H7E 109.5 . . ?
H7C C7C H7E 109.5 . . ?
H7D C7C H7E 109.5 . . ?
C6C C8C H8C 109.5 . . ?
C6C C8C H8D 109.5 . . ?
H8C C8C H8D 109.5 . . ?
C6C C8C H8E 109.5 . . ?
H8C C8C H8E 109.5 . . ?
H8D C8C H8E 109.5 . . ?
C6C C9C H9C 109.5 . . ?
C6C C9C H9D 109.5 . . ?
H9C C9C H9D 109.5 . . ?
C6C C9C H9E 109.5 . . ?
H9C C9C H9E 109.5 . . ?
H9D C9C H9E 109.5 . . ?
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 C12 1.693(3) . ?
S13 C14 1.714(9) . ?
S13B C12 1.715(4) . ?
S13B C14B 1.725(12) . ?
P1 O1 1.4646(18) . ?
P1 O1D 1.537(8) . ?
P1 O1A 1.5768(17) . ?
P1 O1B 1.596(3) . ?
P1 C2 1.818(2) . ?
O10 C10 1.219(3) . ?
O1A C2A 1.461(3) . ?
O1B C2B 1.458(4) . ?
O1D C2D 1.435(14) . ?
O4C C4C 1.213(3) . ?
O5C C4C 1.356(2) . ?
O5C C6C 1.479(2) . ?
N4 C4C 1.364(3) . ?
N4 C5 1.459(3) . ?
N4 C3 1.472(3) . ?
N9 C10 1.354(3) . ?
N9 C2 1.452(3) . ?
N9 H9 0.884(17) . ?
C2 C3 1.554(3) . ?
C2 H2 1.0000 . ?
C3 C8 1.535(3) . ?
C3 H3 1.0000 . ?
C5 C6 1.523(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.527(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.511(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 C11 1.523(3) . ?
C11 C12 1.497(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C16 1.347(9) . ?
C12 C16B 1.384(11) . ?
C14 C15 1.368(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.430(14) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C14B C15B 1.368(12) . ?
C14B H14B 0.9500 . ?
C15B C16B 1.43(2) . ?
C15B H15B 0.9500 . ?
C16B H16B 0.9500 . ?
C2A C3A 1.489(4) . ?
C2A H2A 0.9900 . ?
C2A H2B 0.9900 . ?
C3A H3A 0.9800 . ?
C3A H3B 0.9800 . ?
C3A H3C 0.9800 . ?
C2B C3B 1.490(4) . ?
C2B H2C 0.9900 . ?
C2B H2D 0.9900 . ?
C3B C2D 1.537(9) . ?
C3B H3D 0.9800 . ?
C3B H3E 0.9800 . ?
C3B H3F 0.9800 . ?
C3B H3G 0.9800 . ?
C3B H3H 0.9800 . ?
C3B H3I 0.9800 . ?
C2D H2E 0.9900 . ?
C2D H2F 0.9900 . ?
C6C C7C 1.513(3) . ?
C6C C9C 1.517(3) . ?
C6C C8C 1.519(3) . ?
C7C H7C 0.9800 . ?
C7C H7D 0.9800 . ?
C7C H7E 0.9800 . ?
C8C H8C 0.9800 . ?
C8C H8D 0.9800 . ?
C8C H8E 0.9800 . ?
C9C H9C 0.9800 . ?
C9C H9D 0.9800 . ?
C9C H9E 0.9800 . ?
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 0.884(17) 2.06(2) 2.854(3) 150(2) 2_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 -20.31(19) . . . . ?
O1D P1 O1A C2A -129.5(5) . . . . ?
O1B P1 O1A C2A -151.9(2) . . . . ?
C2 P1 O1A C2A 106.39(17) . . . . ?
O1 P1 O1B C2B -61.2(3) . . . . ?
O1A P1 O1B C2B 66.2(3) . . . . ?
C2 P1 O1B C2B 174.2(3) . . . . ?
O1 P1 O1D C2D -159.1(10) . . . . ?
O1A P1 O1D C2D -41.4(11) . . . . ?
C2 P1 O1D C2D 74.5(11) . . . . ?
C10 N9 C2 C3 -113.4(2) . . . . ?
C10 N9 C2 P1 120.80(19) . . . . ?
O1 P1 C2 N9 70.43(17) . . . . ?
O1D P1 C2 N9 -170.0(5) . . . . ?
O1A P1 C2 N9 -55.32(16) . . . . ?
O1B P1 C2 N9 -161.15(18) . . . . ?
O1 P1 C2 C3 -53.92(19) . . . . ?
O1D P1 C2 C3 65.7(5) . . . . ?
O1A P1 C2 C3 -179.67(15) . . . . ?
O1B P1 C2 C3 74.5(2) . . . . ?
C4C N4 C3 C8 -131.2(2) . . . . ?
C5 N4 C3 C8 52.5(2) . . . . ?
C4C N4 C3 C2 106.0(2) . . . . ?
C5 N4 C3 C2 -70.3(2) . . . . ?
N9 C2 C3 N4 178.68(17) . . . . ?
P1 C2 C3 N4 -59.6(2) . . . . ?
N9 C2 C3 C8 56.9(2) . . . . ?
P1 C2 C3 C8 178.54(16) . . . . ?
C4C N4 C5 C6 128.6(2) . . . . ?
C3 N4 C5 C6 -55.4(3) . . . . ?
N4 C5 C6 C7 54.3(3) . . . . ?
C5 C6 C7 C8 -54.8(3) . . . . ?
C6 C7 C8 C3 53.4(3) . . . . ?
N4 C3 C8 C7 -50.3(3) . . . . ?
C2 C3 C8 C7 72.5(2) . . . . ?
C2 N9 C10 O10 0.4(3) . . . . ?
C2 N9 C10 C11 -178.42(18) . . . . ?
O10 C10 C11 C12 84.4(3) . . . . ?
N9 C10 C11 C12 -96.7(2) . . . . ?
C10 C11 C12 C16 61.4(7) . . . . ?
C10 C11 C12 C16B -125.0(9) . . . . ?
C10 C11 C12 S13 -122.8(2) . . . . ?
C10 C11 C12 S13B 58.9(3) . . . . ?
C14 S13 C12 C16 0.1(8) . . . . ?
C14 S13 C12 C11 -176.2(4) . . . . ?
C14B S13B C12 C16B 3.9(10) . . . . ?
C14B S13B C12 C11 -179.4(5) . . . . ?
C12 S13 C14 C15 0.0(8) . . . . ?
S13 C14 C15 C16 -0.1(11) . . . . ?
C11 C12 C16 C15 175.9(6) . . . . ?
S13 C12 C16 C15 -0.2(11) . . . . ?
C14 C15 C16 C12 0.2(13) . . . . ?
C12 S13B C14B C15B -2.5(12) . . . . ?
S13B C14B C15B C16B 0.3(19) . . . . ?
C11 C12 C16B C15B 178.8(11) . . . . ?
S13B C12 C16B C15B -4.5(17) . . . . ?
C14B C15B C16B C12 3(2) . . . . ?
P1 O1A C2A C3A 172.03(15) . . . . ?
P1 O1B C2B C3B -179.1(2) . . . . ?
P1 O1D C2D C3B -171.2(8) . . . . ?
C6C O5C C4C O4C -1.2(3) . . . . ?
C6C O5C C4C N4 179.50(17) . . . . ?
C5 N4 C4C O4C -177.3(2) . . . . ?
C3 N4 C4C O4C 6.7(3) . . . . ?
C5 N4 C4C O5C 2.0(3) . . . . ?
C3 N4 C4C O5C -173.99(17) . . . . ?
C4C O5C C6C C7C 62.9(3) . . . . ?
C4C O5C C6C C9C -62.0(2) . . . . ?
C4C O5C C6C C8C -179.63(18) . . . . ?
