#------------------------------------------------------------------------------
#$Date: 2023-08-03 03:00:19 +0300 (Thu, 03 Aug 2023) $
#$Revision: 285432 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/71/7247132.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_7247132
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         'C20 H33 N2 O6 P S'
_chemical_formula_sum            'C20 H33 N2 O6 P S'
_chemical_formula_weight         460.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                 94.1990(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7772(2)
_cell_length_b                   13.5168(2)
_cell_length_c                   13.6871(2)
_cell_measurement_reflns_used    11871
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      72.2300
_cell_measurement_theta_min      3.2060
_cell_volume                     2357.51(6)
_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 5.1977
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0120
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21708
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.981
_diffrn_reflns_theta_min         4.570
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.179
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.403
_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    1.297
_exptl_crystal_description       prism
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.995
_refine_diff_density_min         -0.598
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     539
_refine_ls_number_reflns         4473
_refine_ls_number_restraints     284
_refine_ls_restrained_S_all      1.163
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0780
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1177P)²+1.9054P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2175
_refine_ls_wR_factor_ref         0.2255
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3933
_reflns_number_total             4473
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3md00286a2.cif
_cod_data_source_block           4c-2
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7247132
_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   0.561
_shelx_estimated_absorpt_t_max   0.750
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
P1 P 0.55172(17) 0.47154(12) 0.67277(11) 0.0454(4) Uani 0.5 1 d D U P A 1
O1 O 0.5675(5) 0.5596(3) 0.6111(3) 0.0647(12) Uani 0.5 1 d D . P A 1
O1A O 0.5502(10) 0.4877(10) 0.7844(7) 0.065(2) Uani 0.5 1 d D U P A 1
C2A C 0.6357(10) 0.5440(10) 0.8305(7) 0.103(3) Uani 0.5 1 d D U P A 1
H2A1 H 0.702678 0.519808 0.807383 0.124 Uiso 0.5 1 calc R U P A 1
H2A2 H 0.627579 0.614371 0.811482 0.124 Uiso 0.5 1 calc R U P A 1
C3A C 0.6389(11) 0.5361(13) 0.9329(8) 0.114(5) Uani 0.5 1 d D U P A 1
H3A1 H 0.697775 0.575066 0.962164 0.170 Uiso 0.5 1 calc R U P A 1
H3A2 H 0.573103 0.561013 0.956020 0.170 Uiso 0.5 1 calc R U P A 1
H3A3 H 0.648136 0.466533 0.951925 0.170 Uiso 0.5 1 calc R U P A 1
O1B O 0.6343(4) 0.3867(4) 0.6651(2) 0.0580(12) Uani 0.5 1 d D U P A 1
C2B C 0.6735(8) 0.3670(7) 0.5700(5) 0.081(2) Uani 0.5 1 d D U P A 1
H2B1 H 0.618589 0.379995 0.516656 0.097 Uiso 0.5 1 calc R U P A 1
H2B2 H 0.735413 0.408633 0.559595 0.097 Uiso 0.5 1 calc R U P A 1
C3B C 0.7014(11) 0.2640(9) 0.5731(8) 0.086(3) Uani 0.5 1 d D U P A 1
H3B1 H 0.728872 0.244815 0.510857 0.129 Uiso 0.5 1 calc R U P A 1
H3B2 H 0.755294 0.252639 0.626707 0.129 Uiso 0.5 1 calc R U P A 1
H3B3 H 0.639234 0.224188 0.584048 0.129 Uiso 0.5 1 calc R U P A 1
P1D P 0.50501(19) 0.45581(18) 0.65491(17) 0.0666(7) Uani 0.5 1 d D U P A 2
O1D O 0.5050(6) 0.5437(5) 0.5941(4) 0.094(2) Uani 0.5 1 d D U P A 2
O1E O 0.5295(10) 0.4820(12) 0.7670(7) 0.071(3) Uani 0.5 1 d D . P A 2
C2E C 0.5875(8) 0.5698(7) 0.8132(8) 0.088(3) Uani 0.5 1 d D . P A 2
H2E1 H 0.658618 0.573392 0.789187 0.106 Uiso 0.5 1 calc R U P A 2
H2E2 H 0.549730 0.631450 0.793657 0.106 Uiso 0.5 1 calc R U P A 2
C3E C 0.5957(8) 0.5618(10) 0.9165(8) 0.085(3) Uani 0.5 1 d D . P A 2
H3E1 H 0.633411 0.619285 0.944891 0.128 Uiso 0.5 1 calc R U P A 2
H3E2 H 0.525226 0.559226 0.940376 0.128 Uiso 0.5 1 calc R U P A 2
H3E3 H 0.633973 0.501243 0.935911 0.128 Uiso 0.5 1 calc R U P A 2
O1F O 0.5931(9) 0.3797(9) 0.6406(11) 0.195(6) Uani 0.5 1 d D U P A 2
C2F C 0.6887(11) 0.3616(15) 0.6024(15) 0.180(8) Uani 0.5 1 d D U P A 2
H2F1 H 0.744000 0.361827 0.656966 0.216 Uiso 0.5 1 calc R U P A 2
H2F2 H 0.703854 0.416884 0.558079 0.216 Uiso 0.5 1 calc R U P A 2
C3F C 0.696(2) 0.2713(17) 0.5498(19) 0.186(11) Uani 0.5 1 d D U P A 2
H3F1 H 0.766236 0.265494 0.525926 0.279 Uiso 0.5 1 calc R U P A 2
H3F2 H 0.683588 0.215581 0.593217 0.279 Uiso 0.5 1 calc R U P A 2
H3F3 H 0.643333 0.270787 0.494061 0.279 Uiso 0.5 1 calc R U P A 2
C2 C 0.4294(5) 0.4080(4) 0.6509(4) 0.0351(13) Uani 0.5 1 d D . P A 1
H2 H 0.419638 0.365574 0.709424 0.042 Uiso 0.5 1 calc R U P A 1
C3 C 0.3332(6) 0.4783(6) 0.6377(5) 0.0581(15) Uani 0.5 1 d D . P A 1
H3 H 0.340593 0.520311 0.578511 0.070 Uiso 0.5 1 calc R U P A 1
N4 N 0.2393(6) 0.4206(6) 0.6229(5) 0.0613(17) Uani 0.5 1 d D . P A 1
C5 C 0.1991(12) 0.3672(11) 0.7070(9) 0.079(4) Uani 0.5 1 d D . P A 1
H5A H 0.246835 0.311763 0.726191 0.095 Uiso 0.5 1 calc R U P A 1
H5B H 0.129074 0.339197 0.687310 0.095 Uiso 0.5 1 calc R U P A 1
C6 C 0.1907(7) 0.4366(9) 0.7944(7) 0.093(3) Uani 0.5 1 d D U P A 1
H6A H 0.133330 0.484467 0.778306 0.112 Uiso 0.5 1 calc R U P A 1
H6B H 0.171083 0.397086 0.851185 0.112 Uiso 0.5 1 calc R U P A 1
C8 C 0.3206(7) 0.5463(7) 0.7265(6) 0.078(3) Uani 0.5 1 d D U P A 1
H8A H 0.266506 0.596561 0.707511 0.093 Uiso 0.5 1 calc R U P A 1
H8B H 0.387613 0.581708 0.741622 0.093 Uiso 0.5 1 calc R U P A 1
C2D C 0.3873(5) 0.3830(4) 0.6491(4) 0.0376(13) Uani 0.5 1 d D . P A 2
H2D H 0.391669 0.337997 0.707268 0.045 Uiso 0.5 1 calc R U P A 2
C3D C 0.2846(6) 0.4405(4) 0.6500(4) 0.0383(12) Uani 0.5 1 d D . P A 2
H3D H 0.268451 0.467484 0.582541 0.046 Uiso 0.5 1 calc R U P A 2
N4D N 0.2024(7) 0.3697(5) 0.6687(5) 0.0408(14) Uani 0.5 1 d D . P A 2
C5D C 0.1994(5) 0.3323(4) 0.7692(4) 0.0499(13) Uani 0.5 1 d D . P A 2
H5D1 H 0.262247 0.291244 0.786213 0.060 Uiso 0.5 1 calc R U P A 2
H5D2 H 0.136462 0.290284 0.773958 0.060 Uiso 0.5 1 calc R U P A 2
C6D C 0.1962(6) 0.4192(6) 0.8410(5) 0.065(2) Uani 0.5 1 d D . P A 2
H6D1 H 0.203302 0.394254 0.909167 0.078 Uiso 0.5 1 calc R U P A 2
H6D2 H 0.128143 0.454041 0.830835 0.078 Uiso 0.5 1 calc R U P A 2
C8D C 0.2820(6) 0.5267(6) 0.7210(5) 0.0497(17) Uani 0.5 1 d D . P A 2
H8D1 H 0.341427 0.571758 0.711071 0.060 Uiso 0.5 1 calc R U P A 2
H8D2 H 0.216110 0.564350 0.707256 0.060 Uiso 0.5 1 calc R U P A 2
C7 C 0.2887(3) 0.4928(3) 0.8236(2) 0.0777(10) Uani 1 1 d D U . . .
H7A H 0.345073 0.447403 0.849130 0.093 Uiso 0.5 1 calc R U P A 1
H7B H 0.275896 0.542127 0.874897 0.093 Uiso 0.5 1 calc R U P A 1
H7C H 0.285023 0.550521 0.867812 0.093 Uiso 0.5 1 calc R U P A 2
H7D H 0.356822 0.459282 0.839096 0.093 Uiso 0.5 1 calc R U P A 2
N9 N 0.4324(4) 0.3430(4) 0.5669(4) 0.0400(12) Uani 0.5 1 d D . P A 1
H9 H 0.434(5) 0.370(4) 0.507(2) 0.048 Uiso 0.5 1 d D U P B 1
C10 C 0.403(2) 0.2442(9) 0.5661(10) 0.053(3) Uani 0.5 1 d D . P A 1
O10 O 0.4093(19) 0.2005(14) 0.6451(12) 0.064(3) Uani 0.5 1 d D . P A 1
C11 C 0.4093(15) 0.1867(13) 0.4724(11) 0.049(3) Uani 0.5 1 d D . P A 1
C12 C 0.4145(18) 0.2193(11) 0.3898(9) 0.070(4) Uani 0.5 1 d D . P A 1
H12 H 0.418876 0.288201 0.376903 0.085 Uiso 0.5 1 calc R U P A 1
S13 S 0.4133(4) 0.1289(2) 0.2950(3) 0.0637(7) Uani 0.5 1 d D . P A 1
C14 C 0.4303(8) 0.0333(8) 0.3886(9) 0.095(3) Uani 0.5 1 d D . P A 1
H14 H 0.448327 -0.033937 0.378491 0.114 Uiso 0.5 1 calc R U P A 1
C15 C 0.4135(10) 0.0729(8) 0.4693(11) 0.085(4) Uani 0.5 1 d D . P A 1
H15 H 0.403969 0.034166 0.525911 0.102 Uiso 0.5 1 calc R U P A 1
N9D N 0.3862(5) 0.3206(5) 0.5611(4) 0.0437(12) Uani 0.5 1 d D . P A 2
H9D H 0.374(5) 0.360(4) 0.508(3) 0.052 Uiso 0.5 1 d D U P C 2
C10D C 0.412(2) 0.2236(9) 0.5753(9) 0.051(3) Uani 0.5 1 d D . P A 2
O10D O 0.4017(18) 0.1791(13) 0.6509(12) 0.061(3) Uani 0.5 1 d D . P A 2
C11D C 0.403(2) 0.1720(16) 0.4779(13) 0.063(4) Uani 0.5 1 d D U P A 2
C12D C 0.3763(10) 0.0861(11) 0.4725(10) 0.084(3) Uani 0.5 1 d D U P A 2
H12D H 0.356671 0.048497 0.526886 0.101 Uiso 0.5 1 calc R U P A 2
S13D S 0.3778(3) 0.0401(3) 0.3566(2) 0.1064(9) Uani 0.5 1 d D U P A 2
C14D C 0.4044(14) 0.1541(8) 0.3030(11) 0.061(3) Uani 0.5 1 d D U P A 2
H14D H 0.410693 0.168049 0.235662 0.073 Uiso 0.5 1 calc R U P A 2
C15D C 0.4134(15) 0.2144(11) 0.3753(11) 0.068(3) Uani 0.5 1 d D U P A 2
H15D H 0.426167 0.282842 0.365642 0.081 Uiso 0.5 1 calc R U P A 2
C4C C 0.1959(6) 0.4088(5) 0.5265(4) 0.0530(13) Uani 0.5 1 d D . P A 1
O4C O 0.2298(4) 0.4506(3) 0.4572(3) 0.0711(12) Uani 0.5 1 d D . P A 1
O5C O 0.1157(7) 0.3487(6) 0.5216(7) 0.068(3) Uani 0.5 1 d D . P A 1
C6C C 0.0591(11) 0.330(2) 0.4258(9) 0.063(2) Uani 0.5 1 d D U P A 1
C7C C -0.0198(7) 0.2471(8) 0.4547(7) 0.107(3) Uani 0.5 1 d D U P A 1
H7C1 H 0.019742 0.190013 0.481805 0.160 Uiso 0.5 1 calc R U P A 1
H7C2 H -0.064568 0.273140 0.503802 0.160 Uiso 0.5 1 calc R U P A 1
H7C3 H -0.063511 0.226587 0.396373 0.160 Uiso 0.5 1 calc R U P A 1
C8C C 0.0056(7) 0.4161(7) 0.3852(6) 0.093(2) Uani 0.5 1 d D U P A 1
H8C1 H -0.030538 0.399321 0.321793 0.139 Uiso 0.5 1 calc R U P A 1
H8C2 H -0.045706 0.438890 0.430048 0.139 Uiso 0.5 1 calc R U P A 1
H8C3 H 0.056836 0.468714 0.376318 0.139 Uiso 0.5 1 calc R U P A 1
C9C C 0.1313(6) 0.2774(7) 0.3606(7) 0.089(2) Uani 0.5 1 d D U P A 1
H9C1 H 0.163115 0.220313 0.395406 0.134 Uiso 0.5 1 calc R U P A 1
H9C2 H 0.091115 0.254889 0.300977 0.134 Uiso 0.5 1 calc R U P A 1
H9C3 H 0.186517 0.322978 0.342999 0.134 Uiso 0.5 1 calc R U P A 1
C4G C 0.1294(4) 0.3336(3) 0.5983(3) 0.0407(10) Uani 0.5 1 d D . P A 2
O4G O 0.0643(3) 0.2729(3) 0.6144(3) 0.0645(11) Uani 0.5 1 d D . P A 2
O5G O 0.1387(7) 0.3769(6) 0.5105(5) 0.0492(17) Uani 0.5 1 d D . P A 2
C6G C 0.0776(11) 0.338(2) 0.4230(8) 0.057(2) Uani 0.5 1 d D U P A 2
C7G C -0.0402(6) 0.3536(6) 0.4346(6) 0.0782(19) Uani 0.5 1 d D U P A 2
H7G1 H -0.081042 0.327809 0.376758 0.117 Uiso 0.5 1 calc R U P A 2
H7G2 H -0.060291 0.318617 0.493134 0.117 Uiso 0.5 1 calc R U P A 2
H7G3 H -0.054386 0.424447 0.441406 0.117 Uiso 0.5 1 calc R U P A 2
C8G C 0.0992(5) 0.2304(4) 0.4085(4) 0.0537(12) Uani 0.5 1 d D U P A 2
H8G1 H 0.057745 0.206584 0.350126 0.080 Uiso 0.5 1 calc R U P A 2
H8G2 H 0.174012 0.220933 0.399941 0.080 Uiso 0.5 1 calc R U P A 2
H8G3 H 0.079953 0.193113 0.465952 0.080 Uiso 0.5 1 calc R U P A 2
C9G C 0.1178(7) 0.3995(6) 0.3418(4) 0.090(2) Uani 0.5 1 d D U P A 2
H9G1 H 0.082157 0.379697 0.278995 0.134 Uiso 0.5 1 calc R U P A 2
H9G2 H 0.103861 0.469576 0.353854 0.134 Uiso 0.5 1 calc R U P A 2
H9G3 H 0.193575 0.389309 0.339718 0.134 Uiso 0.5 1 calc R U P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
O1 P1 O1A 117.5(6) . . ?
O1 P1 O1B 115.4(3) . . ?
O1A P1 O1B 103.1(6) . . ?
O1 P1 C2 116.4(3) . . ?
O1A P1 C2 99.2(5) . . ?
O1B P1 C2 102.8(3) . . ?
C2A O1A P1 116.4(8) . . ?
C3A C2A O1A 111.4(9) . . ?
C3A C2A H2A1 109.4 . . ?
O1A C2A H2A1 109.4 . . ?
C3A C2A H2A2 109.4 . . ?
O1A C2A H2A2 109.4 . . ?
H2A1 C2A H2A2 108.0 . . ?
C2A C3A H3A1 109.5 . . ?
C2A C3A H3A2 109.5 . . ?
H3A1 C3A H3A2 109.5 . . ?
C2A C3A H3A3 109.5 . . ?
H3A1 C3A H3A3 109.5 . . ?
H3A2 C3A H3A3 109.5 . . ?
C2B O1B P1 118.1(4) . . ?
C3B C2B O1B 104.6(7) . . ?
C3B C2B H2B1 110.8 . . ?
O1B C2B H2B1 110.8 . . ?
C3B C2B H2B2 110.8 . . ?
O1B C2B H2B2 110.8 . . ?
H2B1 C2B H2B2 108.9 . . ?
C2B C3B H3B1 109.5 . . ?
C2B C3B H3B2 109.5 . . ?
H3B1 C3B H3B2 109.5 . . ?
C2B C3B H3B3 109.5 . . ?
H3B1 C3B H3B3 109.5 . . ?
H3B2 C3B H3B3 109.5 . . ?
O1D P1D O1F 116.1(6) . . ?
O1D P1D O1E 111.4(6) . . ?
O1F P1D O1E 100.2(8) . . ?
O1D P1D C2D 117.3(4) . . ?
O1F P1D C2D 104.2(5) . . ?
O1E P1D C2D 105.7(5) . . ?
C2E O1E P1D 129.5(10) . . ?
C3E C2E O1E 110.8(9) . . ?
C3E C2E H2E1 109.5 . . ?
O1E C2E H2E1 109.5 . . ?
C3E C2E H2E2 109.5 . . ?
O1E C2E H2E2 109.5 . . ?
H2E1 C2E H2E2 108.1 . . ?
C2E C3E H3E1 109.5 . . ?
C2E C3E H3E2 109.5 . . ?
H3E1 C3E H3E2 109.5 . . ?
C2E C3E H3E3 109.5 . . ?
H3E1 C3E H3E3 109.5 . . ?
H3E2 C3E H3E3 109.5 . . ?
C2F O1F P1D 146.6(13) . . ?
O1F C2F C3F 115.8(16) . . ?
O1F C2F H2F1 108.3 . . ?
C3F C2F H2F1 108.3 . . ?
O1F C2F H2F2 108.3 . . ?
C3F C2F H2F2 108.3 . . ?
H2F1 C2F H2F2 107.4 . . ?
C2F C3F H3F1 109.5 . . ?
C2F C3F H3F2 109.5 . . ?
H3F1 C3F H3F2 109.5 . . ?
C2F C3F H3F3 109.5 . . ?
H3F1 C3F H3F3 109.5 . . ?
H3F2 C3F H3F3 109.5 . . ?
N9 C2 C3 110.2(5) . . ?
N9 C2 P1 110.5(4) . . ?
C3 C2 P1 113.5(5) . . ?
N9 C2 H2 107.4 . . ?
C3 C2 H2 107.4 . . ?
P1 C2 H2 107.4 . . ?
N4 C3 C8 107.5(7) . . ?
N4 C3 C2 109.3(6) . . ?
C8 C3 C2 113.7(5) . . ?
N4 C3 H3 108.7 . . ?
C8 C3 H3 108.7 . . ?
C2 C3 H3 108.7 . . ?
C4C N4 C3 117.7(7) . . ?
C4C N4 C5 122.6(9) . . ?
C3 N4 C5 119.3(8) . . ?
N4 C5 C6 110.9(10) . . ?
N4 C5 H5A 109.5 . . ?
C6 C5 H5A 109.5 . . ?
N4 C5 H5B 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 108.0 . . ?
C7 C6 C5 114.5(8) . . ?
C7 C6 H6A 108.6 . . ?
C5 C6 H6A 108.6 . . ?
C7 C6 H6B 108.6 . . ?
C5 C6 H6B 108.6 . . ?
H6A C6 H6B 107.6 . . ?
C3 C8 C7 115.8(7) . . ?
C3 C8 H8A 108.3 . . ?
C7 C8 H8A 108.3 . . ?
C3 C8 H8B 108.3 . . ?
C7 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?
N9D C2D C3D 110.0(5) . . ?
N9D C2D P1D 108.0(4) . . ?
C3D C2D P1D 116.0(4) . . ?
N9D C2D H2D 107.5 . . ?
C3D C2D H2D 107.5 . . ?
P1D C2D H2D 107.5 . . ?
N4D C3D C8D 110.0(5) . . ?
N4D C3D C2D 107.3(5) . . ?
C8D C3D C2D 117.1(6) . . ?
N4D C3D H3D 107.4 . . ?
C8D C3D H3D 107.4 . . ?
C2D C3D H3D 107.4 . . ?
C4G N4D C3D 124.7(6) . . ?
C4G N4D C5D 118.0(6) . . ?
C3D N4D C5D 117.4(7) . . ?
N4D C5D C6D 109.9(6) . . ?
N4D C5D H5D1 109.7 . . ?
C6D C5D H5D1 109.7 . . ?
N4D C5D H5D2 109.7 . . ?
C6D C5D H5D2 109.7 . . ?
H5D1 C5D H5D2 108.2 . . ?
C5D C6D C7 109.4(5) . . ?
C5D C6D H6D1 109.8 . . ?
C7 C6D H6D1 109.8 . . ?
C5D C6D H6D2 109.8 . . ?
C7 C6D H6D2 109.8 . . ?
H6D1 C6D H6D2 108.2 . . ?
C7 C8D C3D 111.6(5) . . ?
C7 C8D H8D1 109.3 . . ?
C3D C8D H8D1 109.3 . . ?
C7 C8D H8D2 109.3 . . ?
C3D C8D H8D2 109.3 . . ?
H8D1 C8D H8D2 108.0 . . ?
C8D C7 C6D 110.4(4) . . ?
C6 C7 C8 105.5(6) . . ?
C6 C7 H7A 110.6 . . ?
C8 C7 H7A 110.6 . . ?
C6 C7 H7B 110.6 . . ?
C8 C7 H7B 110.6 . . ?
H7A C7 H7B 108.8 . . ?
C8D C7 H7C 109.6 . . ?
C6D C7 H7C 109.6 . . ?
C8D C7 H7D 109.6 . . ?
C6D C7 H7D 109.6 . . ?
H7C C7 H7D 108.1 . . ?
C10 N9 C2 124.5(7) . . ?
C10 N9 H9 114(4) . . ?
C2 N9 H9 118(4) . . ?
O10 C10 N9 117.1(14) . . ?
O10 C10 C11 119.7(13) . . ?
N9 C10 C11 118.1(13) . . ?
C12 C11 C10 127.7(15) . . ?
C12 C11 C15 109.4(8) . . ?
C10 C11 C15 122.9(14) . . ?
C11 C12 S13 115.4(12) . . ?
C11 C12 H12 122.3 . . ?
S13 C12 H12 122.3 . . ?
C12 S13 C14 88.9(7) . . ?
C15 C14 S13 107.2(9) . . ?
C15 C14 H14 126.4 . . ?
S13 C14 H14 126.4 . . ?
C14 C15 C11 117.2(12) . . ?
C14 C15 H15 121.4 . . ?
C11 C15 H15 121.4 . . ?
C10D N9D C2D 116.6(7) . . ?
C10D N9D H9D 135(4) . . ?
C2D N9D H9D 108(4) . . ?
O10D C10D N9D 123.8(15) . . ?
O10D C10D C11D 121.3(16) . . ?
N9D C10D C11D 108.5(13) . . ?
C12D C11D C10D 120.2(19) . . ?
C12D C11D C15D 110.3(11) . . ?
C10D C11D C15D 129.3(17) . . ?
C11D C12D S13D 112.6(12) . . ?
C11D C12D H12D 123.7 . . ?
S13D C12D H12D 123.7 . . ?
C12D S13D C14D 94.8(7) . . ?
C15D C14D S13D 104.2(11) . . ?
C15D C14D H14D 127.9 . . ?
S13D C14D H14D 127.9 . . ?
C14D C15D C11D 117.5(14) . . ?
C14D C15D H15D 121.3 . . ?
C11D C15D H15D 121.3 . . ?
O4C C4C O5C 125.2(7) . . ?
O4C C4C N4 122.9(8) . . ?
O5C C4C N4 112.0(8) . . ?
C4C O5C C6C 119.1(10) . . ?
C8C C6C O5C 113.0(17) . . ?
C8C C6C C9C 116.5(12) . . ?
O5C C6C C9C 109.0(13) . . ?
C8C C6C C7C 112.2(12) . . ?
O5C C6C C7C 100.4(12) . . ?
C9C C6C C7C 104.2(17) . . ?
C6C C7C H7C1 109.5 . . ?
C6C C7C H7C2 109.5 . . ?
H7C1 C7C H7C2 109.5 . . ?
C6C C7C H7C3 109.5 . . ?
H7C1 C7C H7C3 109.5 . . ?
H7C2 C7C H7C3 109.5 . . ?
C6C C8C H8C1 109.5 . . ?
C6C C8C H8C2 109.5 . . ?
H8C1 C8C H8C2 109.5 . . ?
C6C C8C H8C3 109.5 . . ?
H8C1 C8C H8C3 109.5 . . ?
H8C2 C8C H8C3 109.5 . . ?
C6C C9C H9C1 109.5 . . ?
C6C C9C H9C2 109.5 . . ?
H9C1 C9C H9C2 109.5 . . ?
C6C C9C H9C3 109.5 . . ?
H9C1 C9C H9C3 109.5 . . ?
H9C2 C9C H9C3 109.5 . . ?
O4G C4G O5G 124.5(5) . . ?
O4G C4G N4D 123.8(5) . . ?
O5G C4G N4D 111.7(5) . . ?
C4G O5G C6G 119.4(9) . . ?
O5G C6G C8G 111.3(15) . . ?
O5G C6G C9G 102.2(10) . . ?
C8G C6G C9G 111.3(11) . . ?
O5G C6G C7G 109.2(11) . . ?
C8G C6G C7G 109.8(10) . . ?
C9G C6G C7G 112.8(16) . . ?
C6G C7G H7G1 109.5 . . ?
C6G C7G H7G2 109.5 . . ?
H7G1 C7G H7G2 109.5 . . ?
C6G C7G H7G3 109.5 . . ?
H7G1 C7G H7G3 109.5 . . ?
H7G2 C7G H7G3 109.5 . . ?
C6G C8G H8G1 109.5 . . ?
C6G C8G H8G2 109.5 . . ?
H8G1 C8G H8G2 109.5 . . ?
C6G C8G H8G3 109.5 . . ?
H8G1 C8G H8G3 109.5 . . ?
H8G2 C8G H8G3 109.5 . . ?
C6G C9G H9G1 109.5 . . ?
C6G C9G H9G2 109.5 . . ?
H9G1 C9G H9G2 109.5 . . ?
C6G C9G H9G3 109.5 . . ?
H9G1 C9G H9G3 109.5 . . ?
H9G2 C9G H9G3 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
P1 O1 1.482(4) . ?
P1 O1A 1.545(8) . ?
P1 O1B 1.567(5) . ?
P1 C2 1.790(6) . ?
O1A C2A 1.438(12) . ?
C2A C3A 1.402(12) . ?
C2A H2A1 0.9900 . ?
C2A H2A2 0.9900 . ?
C3A H3A1 0.9800 . ?
C3A H3A2 0.9800 . ?
C3A H3A3 0.9800 . ?
O1B C2B 1.454(6) . ?
C2B C3B 1.437(12) . ?
C2B H2B1 0.9900 . ?
C2B H2B2 0.9900 . ?
C3B H3B1 0.9800 . ?
C3B H3B2 0.9800 . ?
C3B H3B3 0.9800 . ?
P1D O1D 1.450(6) . ?
P1D O1F 1.548(7) . ?
P1D O1E 1.583(9) . ?
P1D C2D 1.794(7) . ?
O1E C2E 1.512(12) . ?
C2E C3E 1.415(12) . ?
C2E H2E1 0.9900 . ?
C2E H2E2 0.9900 . ?
C3E H3E1 0.9800 . ?
C3E H3E2 0.9800 . ?
C3E H3E3 0.9800 . ?
O1F C2F 1.386(8) . ?
C2F C3F 1.423(15) . ?
C2F H2F1 0.9900 . ?
C2F H2F2 0.9900 . ?
C3F H3F1 0.9800 . ?
C3F H3F2 0.9800 . ?
C3F H3F3 0.9800 . ?
C2 N9 1.450(8) . ?
C2 C3 1.553(8) . ?
C2 H2 1.0000 . ?
C3 N4 1.433(9) . ?
C3 C8 1.541(9) . ?
C3 H3 1.0000 . ?
N4 C4C 1.402(9) . ?
N4 C5 1.482(11) . ?
C5 C6 1.531(12) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.495(9) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 C7 1.592(10) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C2D N9D 1.469(8) . ?
C2D C3D 1.526(8) . ?
C2D H2D 1.0000 . ?
C3D N4D 1.458(10) . ?
C3D C8D 1.520(9) . ?
C3D H3D 1.0000 . ?
N4D C4G 1.379(10) . ?
N4D C5D 1.469(6) . ?
C5D C6D 1.534(9) . ?
C5D H5D1 0.9900 . ?
C5D H5D2 0.9900 . ?
C6D C7 1.577(8) . ?
C6D H6D1 0.9900 . ?
C6D H6D2 0.9900 . ?
C8D C7 1.474(8) . ?
C8D H8D1 0.9900 . ?
C8D H8D2 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 H7C 0.9900 . ?
C7 H7D 0.9900 . ?
N9 C10 1.386(15) . ?
N9 H9 0.90(2) . ?
C10 O10 1.229(11) . ?
C10 C11 1.508(10) . ?
C11 C12 1.22(2) . ?
C11 C15 1.54(2) . ?
C12 S13 1.781(13) . ?
C12 H12 0.9500 . ?
S13 C14 1.822(10) . ?
C14 C15 1.259(17) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N9D C10D 1.363(13) . ?
N9D H9D 0.91(2) . ?
C10D O10D 1.214(12) . ?
C10D C11D 1.501(11) . ?
C11D C12D 1.21(2) . ?
C11D C15D 1.53(2) . ?
C12D S13D 1.706(13) . ?
C12D H12D 0.9500 . ?
S13D C14D 1.750(13) . ?
C14D C15D 1.281(19) . ?
C14D H14D 0.9500 . ?
C15D H15D 0.9500 . ?
C4C O4C 1.211(7) . ?
C4C O5C 1.304(9) . ?
O5C C6C 1.474(11) . ?
C6C C8C 1.44(3) . ?
C6C C9C 1.51(2) . ?
C6C C7C 1.575(19) . ?
C7C H7C1 0.9800 . ?
C7C H7C2 0.9800 . ?
C7C H7C3 0.9800 . ?
C8C H8C1 0.9800 . ?
C8C H8C2 0.9800 . ?
C8C H8C3 0.9800 . ?
C9C H9C1 0.9800 . ?
C9C H9C2 0.9800 . ?
C9C H9C3 0.9800 . ?
C4G O4G 1.201(6) . ?
C4G O5G 1.350(8) . ?
O5G C6G 1.478(10) . ?
C6G C8G 1.49(3) . ?
C6G C9G 1.510(17) . ?
C6G C7G 1.541(17) . ?
C7G H7G1 0.9800 . ?
C7G H7G2 0.9800 . ?
C7G H7G3 0.9800 . ?
C8G H8G1 0.9800 . ?
C8G H8G2 0.9800 . ?
C8G H8G3 0.9800 . ?
C9G H9G1 0.9800 . ?
C9G H9G2 0.9800 . ?
C9G H9G3 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 0.90(2) 1.87(2) 2.769(7) 174(5) 3_666 yes
N9D H9D O1D 0.91(2) 2.52(5) 3.200(8) 132(5) 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 -50.0(14) . . . . ?
O1B P1 O1A C2A 78.3(12) . . . . ?
C2 P1 O1A C2A -176.2(11) . . . . ?
P1 O1A C2A C3A -167.2(12) . . . . ?
O1 P1 O1B C2B -36.9(8) . . . . ?
O1A P1 O1B C2B -166.5(8) . . . . ?
C2 P1 O1B C2B 90.8(7) . . . . ?
P1 O1B C2B C3B -152.3(8) . . . . ?
O1D P1D O1E C2E -24.2(15) . . . . ?
O1F P1D O1E C2E 99.3(14) . . . . ?
C2D P1D O1E C2E -152.7(12) . . . . ?
P1D O1E C2E C3E -177.3(11) . . . . ?
O1D P1D O1F C2F 15(3) . . . . ?
O1E P1D O1F C2F -105(3) . . . . ?
C2D P1D O1F C2F 146(3) . . . . ?
P1D O1F C2F C3F -134(2) . . . . ?
O1 P1 C2 N9 80.9(5) . . . . ?
O1A P1 C2 N9 -152.1(7) . . . . ?
O1B P1 C2 N9 -46.3(4) . . . . ?
O1 P1 C2 C3 -43.5(5) . . . . ?
O1A P1 C2 C3 83.5(7) . . . . ?
O1B P1 C2 C3 -170.7(4) . . . . ?
N9 C2 C3 N4 56.7(7) . . . . ?
P1 C2 C3 N4 -178.7(4) . . . . ?
N9 C2 C3 C8 176.8(7) . . . . ?
P1 C2 C3 C8 -58.6(8) . . . . ?
C8 C3 N4 C4C 136.5(6) . . . . ?
C2 C3 N4 C4C -99.7(6) . . . . ?
C8 C3 N4 C5 -50.3(10) . . . . ?
C2 C3 N4 C5 73.5(9) . . . . ?
C4C N4 C5 C6 -136.2(9) . . . . ?
C3 N4 C5 C6 51.0(13) . . . . ?
N4 C5 C6 C7 -52.3(15) . . . . ?
N4 C3 C8 C7 52.6(7) . . . . ?
C2 C3 C8 C7 -68.6(9) . . . . ?
O1D P1D C2D N9D 80.3(5) . . . . ?
O1F P1D C2D N9D -49.6(7) . . . . ?
O1E P1D C2D N9D -154.8(7) . . . . ?
O1D P1D C2D C3D -43.7(6) . . . . ?
O1F P1D C2D C3D -173.6(7) . . . . ?
O1E P1D C2D C3D 81.2(8) . . . . ?
N9D C2D C3D N4D 70.6(7) . . . . ?
P1D C2D C3D N4D -166.5(5) . . . . ?
N9D C2D C3D C8D -165.3(5) . . . . ?
P1D C2D C3D C8D -42.4(6) . . . . ?
C8D C3D N4D C4G 128.2(7) . . . . ?
C2D C3D N4D C4G -103.4(8) . . . . ?
C8D C3D N4D C5D -53.6(9) . . . . ?
C2D C3D N4D C5D 74.7(8) . . . . ?
C4G N4D C5D C6D -127.9(6) . . . . ?
C3D N4D C5D C6D 53.8(9) . . . . ?
N4D C5D C6D C7 -52.3(8) . . . . ?
N4D C3D C8D C7 54.7(8) . . . . ?
C2D C3D C8D C7 -68.1(7) . . . . ?
C3D C8D C7 C6D -57.8(7) . . . . ?
C5 C6 C7 C8 53.4(11) . . . . ?
C5D C6D C7 C8D 56.7(7) . . . . ?
C3 C8 C7 C6 -55.1(8) . . . . ?
C3 C2 N9 C10 -103.5(15) . . . . ?
P1 C2 N9 C10 130.2(14) . . . . ?
C2 N9 C10 O10 -26(3) . . . . ?
C2 N9 C10 C11 179.3(13) . . . . ?
O10 C10 C11 C12 -172(3) . . . . ?
N9 C10 C11 C12 -18(4) . . . . ?
O10 C10 C11 C15 6(4) . . . . ?
N9 C10 C11 C15 159.9(16) . . . . ?
C10 C11 C12 S13 -176(2) . . . . ?
C15 C11 C12 S13 5(2) . . . . ?
C11 C12 S13 C14 -10.5(18) . . . . ?
C12 S13 C14 C15 12.8(12) . . . . ?
S13 C14 C15 C11 -13.1(15) . . . . ?
C12 C11 C15 C14 6(2) . . . . ?
C10 C11 C15 C14 -172.5(19) . . . . ?
C3D C2D N9D C10D -129.9(15) . . . . ?
P1D C2D N9D C10D 102.6(15) . . . . ?
C2D N9D C10D O10D 26(3) . . . . ?
C2D N9D C10D C11D 177.9(15) . . . . ?
O10D C10D C11D C12D 6(4) . . . . ?
N9D C10D C11D C12D -147(2) . . . . ?
O10D C10D C11D C15D 180(3) . . . . ?
N9D C10D C11D C15D 27(4) . . . . ?
C10D C11D C12D S13D -176.4(19) . . . . ?
C15D C11D C12D S13D 8(2) . . . . ?
C11D C12D S13D C14D -6.8(18) . . . . ?
C12D S13D C14D C15D 2.3(15) . . . . ?
S13D C14D C15D C11D 2(2) . . . . ?
C12D C11D C15D C14D -7(3) . . . . ?
C10D C11D C15D C14D 178(2) . . . . ?
C3 N4 C4C O4C -5.4(9) . . . . ?
C5 N4 C4C O4C -178.4(9) . . . . ?
C3 N4 C4C O5C 174.9(7) . . . . ?
C5 N4 C4C O5C 2.0(12) . . . . ?
O4C C4C O5C C6C -1.1(18) . . . . ?
N4 C4C O5C C6C 178.5(14) . . . . ?
C4C O5C C6C C8C -66.1(14) . . . . ?
C4C O5C C6C C9C 65(2) . . . . ?
C4C O5C C6C C7C 174.2(10) . . . . ?
C3D N4D C4G O4G 177.5(6) . . . . ?
C5D N4D C4G O4G -0.7(10) . . . . ?
C3D N4D C4G O5G -4.1(10) . . . . ?
C5D N4D C4G O5G 177.7(7) . . . . ?
O4G C4G O5G C6G -10.4(16) . . . . ?
N4D C4G O5G C6G 171.2(13) . . . . ?
C4G O5G C6G C8G -56.1(12) . . . . ?
C4G O5G C6G C9G -175.0(10) . . . . ?
C4G O5G C6G C7G 65(2) . . . . ?
