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#$Date: 2023-08-03 03:00:19 +0300 (Thu, 03 Aug 2023) $
#$Revision: 285432 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/71/7247141.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_7247141
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_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
_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                109.022(5)
_cell_angle_beta                 90.103(4)
_cell_angle_gamma                99.548(4)
_cell_formula_units_Z            2
_cell_length_a                   8.8287(4)
_cell_length_b                   10.6334(6)
_cell_length_c                   14.2157(7)
_cell_measurement_reflns_used    3282
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.5290
_cell_measurement_theta_min      2.7070
_cell_volume                     1241.97(12)
_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 0.875
_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  0.0208
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.875
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10578
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.787
_diffrn_reflns_theta_min         2.058
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.968
_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    1.269
_exptl_crystal_description       prism
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         6223
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0431
_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)+(0.0348P)²+0.5856P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.1023
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4935
_reflns_number_total             6223
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3md00286a2.cif
_cod_data_source_block           4j-1
_cod_database_code               7247141
_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   0.959
_shelx_estimated_absorpt_t_max   0.979
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
S14 S 0.14100(6) 0.01995(5) 0.24541(3) 0.02859(12) Uani 1 1 d . . . . .
P1 P 0.52756(5) 0.38977(4) 0.63131(3) 0.01727(10) Uani 1 1 d . . . . .
O1 O 0.62789(14) 0.46535(13) 0.57780(9) 0.0245(3) Uani 1 1 d . . . . .
O10 O 0.05971(14) 0.31109(12) 0.62197(9) 0.0243(3) Uani 1 1 d . . . . .
O1A O 0.47141(14) 0.23633(12) 0.56848(9) 0.0231(3) Uani 1 1 d . . . . .
O1B O 0.59898(14) 0.38220(12) 0.72992(8) 0.0213(3) Uani 1 1 d . . . . .
O4C O 0.65304(17) 0.76488(15) 0.84550(10) 0.0418(4) Uani 1 1 d . . . . .
O5C O 0.56393(14) 0.73715(12) 0.98824(9) 0.0251(3) Uani 1 1 d . . . . .
N4 N 0.43392(16) 0.61725(14) 0.84229(10) 0.0186(3) Uani 1 1 d . . . . .
N9 N 0.26301(16) 0.43936(14) 0.58050(10) 0.0165(3) Uani 1 1 d D . . . .
H9 H 0.300(2) 0.4707(18) 0.5338(12) 0.020 Uiso 1 1 d D U . . .
C2 C 0.35491(19) 0.45911(16) 0.67118(11) 0.0160(3) Uani 1 1 d . . . . .
H2 H 0.296086 0.403815 0.708500 0.019 Uiso 1 1 calc R U . . .
C3 C 0.3864(2) 0.60913(16) 0.74084(12) 0.0195(3) Uani 1 1 d . . . . .
H3 H 0.473167 0.658907 0.714688 0.023 Uiso 1 1 calc R U . . .
C5 C 0.3133(2) 0.56623(17) 0.89812(12) 0.0198(3) Uani 1 1 d . . . . .
H5A H 0.356343 0.577602 0.965346 0.024 Uiso 1 1 calc R U . . .
H5B H 0.276881 0.468561 0.863423 0.024 Uiso 1 1 calc R U . . .
C6 C 0.1788(2) 0.64104(19) 0.90782(13) 0.0266(4) Uani 1 1 d . . . . .
H6A H 0.212257 0.736901 0.949100 0.032 Uiso 1 1 calc R U . . .
H6B H 0.095570 0.600640 0.941233 0.032 Uiso 1 1 calc R U . . .
C7 C 0.1189(2) 0.6325(2) 0.80469(14) 0.0304(4) Uani 1 1 d . . . . .
H7A H 0.072429 0.537792 0.766905 0.037 Uiso 1 1 calc R U . . .
H7B H 0.037774 0.688527 0.811865 0.037 Uiso 1 1 calc R U . . .
C8 C 0.2481(2) 0.68127(18) 0.74711(13) 0.0278(4) Uani 1 1 d . . . . .
H8A H 0.283095 0.779598 0.779792 0.033 Uiso 1 1 calc R U . . .
H8B H 0.207404 0.666703 0.678728 0.033 Uiso 1 1 calc R U . . .
C10 C 0.12066(19) 0.36262(16) 0.56264(12) 0.0176(3) Uani 1 1 d . . . . .
C11 C 0.0404(2) 0.34096(17) 0.46258(12) 0.0204(3) Uani 1 1 d . . . . .
H11A H -0.069673 0.347100 0.471229 0.024 Uiso 1 1 calc R U . . .
H11B H 0.087342 0.412242 0.435552 0.024 Uiso 1 1 calc R U . . .
C12 C 0.05490(19) 0.20372(16) 0.39049(12) 0.0185(3) Uani 1 1 d . . . . .
C13 C 0.1366(2) 0.18698(17) 0.30777(13) 0.0230(4) Uani 1 1 d . . . . .
H13 H 0.185391 0.259211 0.286925 0.028 Uiso 1 1 calc R U . . .
C15 C 0.0312(2) -0.02956(18) 0.33087(14) 0.0270(4) Uani 1 1 d . . . . .
H15 H 0.000582 -0.120854 0.327778 0.032 Uiso 1 1 calc R U . . .
C16 C -0.0067(2) 0.07850(17) 0.40372(13) 0.0232(4) Uani 1 1 d . . . . .
H16 H -0.067384 0.071096 0.457401 0.028 Uiso 1 1 calc R U . . .
C2A C 0.4474(2) 0.18952(19) 0.46046(13) 0.0283(4) Uani 1 1 d . . . . .
H2A1 H 0.446245 0.267793 0.437457 0.034 Uiso 1 1 calc R U . . .
H2A2 H 0.346519 0.128785 0.440302 0.034 Uiso 1 1 calc R U . . .
C3A C 0.5723(3) 0.1157(2) 0.41269(17) 0.0412(5) Uani 1 1 d . . . . .
H3A1 H 0.554411 0.084877 0.340047 0.062 Uiso 1 1 calc R U . . .
H3A2 H 0.671977 0.176266 0.431937 0.062 Uiso 1 1 calc R U . . .
H3A3 H 0.572406 0.037474 0.434777 0.062 Uiso 1 1 calc R U . . .
C2B C 0.7384(2) 0.3249(2) 0.72622(14) 0.0350(5) Uani 1 1 d . . . . .
H2B1 H 0.816850 0.366955 0.690666 0.042 Uiso 1 1 calc R U . . .
H2B2 H 0.715825 0.226429 0.690144 0.042 Uiso 1 1 calc R U . . .
C3B C 0.7972(2) 0.3516(2) 0.83078(14) 0.0316(4) Uani 1 1 d . . . . .
H3B1 H 0.891359 0.313719 0.829890 0.047 Uiso 1 1 calc R U . . .
H3B2 H 0.819812 0.449283 0.865767 0.047 Uiso 1 1 calc R U . . .
H3B3 H 0.719140 0.309247 0.865247 0.047 Uiso 1 1 calc R U . . .
C4C C 0.5591(2) 0.71169(18) 0.88905(13) 0.0244(4) Uani 1 1 d . . . . .
C6C C 0.6980(2) 0.82761(18) 1.05178(13) 0.0253(4) Uani 1 1 d . . . . .
C7C C 0.7179(3) 0.96821(19) 1.04305(16) 0.0366(5) Uani 1 1 d . . . . .
H7C1 H 0.807139 1.025924 1.085714 0.055 Uiso 1 1 calc R U . . .
H7C2 H 0.734065 0.962194 0.973645 0.055 Uiso 1 1 calc R U . . .
H7C3 H 0.625357 1.007053 1.064175 0.055 Uiso 1 1 calc R U . . .
C8C C 0.6515(2) 0.8320(2) 1.15550(14) 0.0333(5) Uani 1 1 d . . . . .
H8C1 H 0.733091 0.890092 1.204869 0.050 Uiso 1 1 calc R U . . .
H8C2 H 0.555842 0.868305 1.169106 0.050 Uiso 1 1 calc R U . . .
H8C3 H 0.635770 0.740479 1.159434 0.050 Uiso 1 1 calc R U . . .
C9C C 0.8408(2) 0.7646(2) 1.02499(15) 0.0332(4) Uani 1 1 d . . . . .
H9C1 H 0.929471 0.824449 1.067039 0.050 Uiso 1 1 calc R U . . .
H9C2 H 0.825774 0.677040 1.035834 0.050 Uiso 1 1 calc R U . . .
H9C3 H 0.859458 0.751507 0.954777 0.050 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 91.70(9) . . ?
O1 P1 O1B 116.56(7) . . ?
O1 P1 O1A 113.71(7) . . ?
O1B P1 O1A 102.74(6) . . ?
O1 P1 C2 113.40(7) . . ?
O1B P1 C2 103.06(7) . . ?
O1A P1 C2 106.06(7) . . ?
C2A O1A P1 122.35(11) . . ?
C2B O1B P1 118.99(11) . . ?
C4C O5C C6C 120.11(14) . . ?
C4C N4 C5 121.95(14) . . ?
C4C N4 C3 117.51(13) . . ?
C5 N4 C3 115.78(13) . . ?
C10 N9 C2 120.47(13) . . ?
N9 C2 C3 112.60(12) . . ?
N9 C2 P1 106.32(10) . . ?
C3 C2 P1 114.08(12) . . ?
N4 C3 C8 108.41(13) . . ?
N4 C3 C2 110.11(12) . . ?
C8 C3 C2 113.91(14) . . ?
N4 C5 C6 110.96(13) . . ?
C5 C6 C7 109.86(14) . . ?
C8 C7 C6 111.07(16) . . ?
C7 C8 C3 113.18(14) . . ?
O10 C10 N9 122.91(15) . . ?
O10 C10 C11 121.29(15) . . ?
N9 C10 C11 115.79(14) . . ?
C12 C11 C10 109.92(13) . . ?
C13 C12 C16 112.31(15) . . ?
C13 C12 C11 123.03(15) . . ?
C16 C12 C11 124.58(15) . . ?
C12 C13 S14 111.93(13) . . ?
C16 C15 S14 111.52(14) . . ?
C15 C16 C12 112.53(16) . . ?
O1A C2A C3A 110.53(16) . . ?
O1B C2B C3B 108.21(15) . . ?
O4C C4C O5C 124.95(16) . . ?
O4C C4C N4 123.46(16) . . ?
O5C C4C N4 111.59(15) . . ?
O5C C6C C9C 109.49(14) . . ?
O5C C6C C8C 102.05(15) . . ?
C9C C6C C8C 111.40(16) . . ?
O5C C6C C7C 111.11(15) . . ?
C9C C6C C7C 112.06(17) . . ?
C8C C6C C7C 110.30(16) . . ?
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 1.7143(18) . ?
S14 C15 1.7161(19) . ?
P1 O1 1.4744(12) . ?
P1 O1B 1.5673(12) . ?
P1 O1A 1.5767(13) . ?
P1 C2 1.8143(16) . ?
O10 C10 1.2272(19) . ?
O1A C2A 1.455(2) . ?
O1B C2B 1.455(2) . ?
O4C C4C 1.210(2) . ?
O5C C4C 1.346(2) . ?
O5C C6C 1.481(2) . ?
N4 C4C 1.366(2) . ?
N4 C5 1.466(2) . ?
N4 C3 1.472(2) . ?
N9 C10 1.354(2) . ?
N9 C2 1.458(2) . ?
C2 C3 1.557(2) . ?
C3 C8 1.534(2) . ?
C5 C6 1.518(2) . ?
C6 C7 1.527(2) . ?
C7 C8 1.525(3) . ?
C10 C11 1.519(2) . ?
C11 C12 1.511(2) . ?
C12 C13 1.358(2) . ?
C12 C16 1.424(2) . ?
C15 C16 1.363(2) . ?
C2A C3A 1.495(3) . ?
C2B C3B 1.494(3) . ?
C6C C9C 1.517(3) . ?
C6C C8C 1.519(3) . ?
C6C C7C 1.522(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 0.876(14) 1.987(14) 2.8617(18) 176.1(18) 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 -30.85(15) . . . . ?
O1B P1 O1A C2A -157.72(13) . . . . ?
C2 P1 O1A C2A 94.45(14) . . . . ?
O1 P1 O1B C2B -57.72(16) . . . . ?
O1A P1 O1B C2B 67.30(15) . . . . ?
C2 P1 O1B C2B 177.40(14) . . . . ?
C10 N9 C2 C3 -115.56(16) . . . . ?
C10 N9 C2 P1 118.83(14) . . . . ?
O1 P1 C2 N9 66.39(12) . . . . ?
O1B P1 C2 N9 -166.70(10) . . . . ?
O1A P1 C2 N9 -59.10(11) . . . . ?
O1 P1 C2 C3 -58.32(13) . . . . ?
O1B P1 C2 C3 68.59(12) . . . . ?
O1A P1 C2 C3 176.19(10) . . . . ?
C4C N4 C3 C8 -101.30(18) . . . . ?
C5 N4 C3 C8 54.78(18) . . . . ?
C4C N4 C3 C2 133.48(16) . . . . ?
C5 N4 C3 C2 -70.45(17) . . . . ?
N9 C2 C3 N4 161.89(13) . . . . ?
P1 C2 C3 N4 -76.83(15) . . . . ?
N9 C2 C3 C8 39.86(19) . . . . ?
P1 C2 C3 C8 161.15(12) . . . . ?
C4C N4 C5 C6 96.77(19) . . . . ?
C3 N4 C5 C6 -58.15(18) . . . . ?
N4 C5 C6 C7 55.1(2) . . . . ?
C5 C6 C7 C8 -53.8(2) . . . . ?
C6 C7 C8 C3 53.6(2) . . . . ?
N4 C3 C8 C7 -51.78(19) . . . . ?
C2 C3 C8 C7 71.18(18) . . . . ?
C2 N9 C10 O10 3.0(2) . . . . ?
C2 N9 C10 C11 -175.77(13) . . . . ?
O10 C10 C11 C12 -78.66(19) . . . . ?
N9 C10 C11 C12 100.12(16) . . . . ?
C10 C11 C12 C13 -113.80(18) . . . . ?
C10 C11 C12 C16 62.4(2) . . . . ?
C16 C12 C13 S14 -0.38(19) . . . . ?
C11 C12 C13 S14 176.24(12) . . . . ?
C15 S14 C13 C12 0.19(14) . . . . ?
C13 S14 C15 C16 0.06(15) . . . . ?
S14 C15 C16 C12 -0.3(2) . . . . ?
C13 C12 C16 C15 0.4(2) . . . . ?
C11 C12 C16 C15 -176.12(16) . . . . ?
P1 O1A C2A C3A 106.95(16) . . . . ?
P1 O1B C2B C3B 170.15(13) . . . . ?
C6C O5C C4C O4C -5.4(3) . . . . ?
C6C O5C C4C N4 174.57(14) . . . . ?
C5 N4 C4C O4C -172.93(17) . . . . ?
C3 N4 C4C O4C -18.4(3) . . . . ?
C5 N4 C4C O5C 7.1(2) . . . . ?
C3 N4 C4C O5C 161.61(14) . . . . ?
C4C O5C C6C C9C -64.4(2) . . . . ?
C4C O5C C6C C8C 177.51(15) . . . . ?
C4C O5C C6C C7C 59.9(2) . . . . ?
