Organometallic Small Molecule Kinase Inhibitors – Direct Incorporation of Re and 99mTc into Opaganib®
Alberto, Roger; Lengacher, Raphael; Wang, Youchao; Braband, Henrik; Blacque, Olivier; Gasser, Gilles; Chemical Communications  (2021) –; doi:10.1039/D1CC03678E

data_7129275
_publ_section_title
;
 Organometallic Small Molecule Kinase Inhibitors -- Direct Incorporation
 of Re and 99mTc into Opaganib&#x00AE;
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC03678E
_journal_year                    2021
_chemical_formula_moiety         'C18 H14 Cl O5 Re'
_chemical_formula_sum            'C18 H14 Cl O5 Re'
_chemical_formula_weight         531.94
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-04-12
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-07-06 deposited with the CCDC.	2021-11-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.583(2)
_cell_angle_beta                 103.616(2)
_cell_angle_gamma                90.8300(10)
_cell_formula_units_Z            2
_cell_length_a                   9.1670(2)
_cell_length_b                   9.36020(10)
_cell_length_c                   10.2239(2)
_cell_measurement_reflns_used    17565
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      79.0920
_cell_measurement_theta_min      4.4380
_cell_volume                     852.43(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -122.00 -55.00   0.50    0.10    --  -49.87-150.00 143.00  134
  2  \w   -125.00 -75.00   0.50    0.10    --  -49.87-122.00 -54.00  100
  3  \w   -105.00 -25.00   0.50    0.10    --  -49.87 150.00-171.00  160
  4  \w    -85.00 -10.00   0.50    0.10    --  -49.87 122.00  26.00  150
  5  \w     32.00  97.00   0.50    0.10    --   49.87-122.00 -54.00  130
  6  \w     47.00 114.00   0.50    0.10    --   49.87-150.00 143.00  134
  7  \w    -85.00 -13.00   0.50    0.20    --  -88.50 122.00  26.00  144
  8  \w   -150.00 -55.00   0.50    0.20    --  -88.50-150.00 143.00  190
  9  \w     77.00 166.00   0.50    0.20    --  110.00 150.00-171.00  178
 10  \w     96.00 178.00   0.50    0.20    --  110.00 122.00  26.00  164
 11  \w     35.00 111.00   0.50    0.20    --  110.00-122.00 -54.00  152
 12  \w     47.00 130.00   0.50    0.20    --  110.00-150.00 143.00  166
 13  \w   -123.00 -34.00   0.50    0.10    --  -49.87 -57.00 -60.00  178
 14  \w   -124.00 -26.00   0.50    0.10    --  -49.87 -77.00  60.00  196
 15  \w   -125.00 -73.00   0.50    0.10    --  -49.87-125.00 -30.00  104
 16  \w   -128.00 -35.00   0.50    0.10    --  -49.87 -37.00-180.00  186
 17  \w   -162.00 -65.00   0.50    0.20    --  -88.50 -76.00  15.48  194
 18  \w   -164.00 -75.00   0.50    0.20    --  -88.50-122.00 -54.00  178
 19  \w     91.00 178.00   0.50    0.20    --  110.00  66.00   8.29  174
 20  \w     34.00 124.00   0.50    0.20    --  110.00 -45.00  90.00  180
 21  \w     36.00 134.00   0.50    0.20    --  110.00 -77.00  90.00  196
 22  \w     34.00 108.00   0.50    0.20    --  110.00-111.00  30.00  148
 23  \w     34.00 107.00   0.50    0.20    --  110.00 -94.00 120.00  146
 24  \w     34.00 108.00   0.50    0.20    --  110.00-111.00 -30.00  148
 25  \w     94.00 178.00   0.50    0.20    --  110.00  15.00  90.00  168
 26  \w    102.00 178.00   0.50    0.20    --  110.00 111.00  90.00  152
 27  \w     38.00 127.00   0.50    0.20    --  110.00 -61.00  90.00  178
 28  \w     96.00 178.00   0.50    0.20    --  110.00  45.00 120.00  164
 29  \w     62.00 146.00   0.50    0.20    --  110.00 178.00  90.00  168
 30  \w     34.00 124.00   0.50    0.20    --  110.00 -45.00-180.00  180
 31  \w     34.00 107.00   0.50    0.20    --  110.00 -94.00  60.00  146
 32  \w     94.00 178.00   0.50    0.20    --  110.00  15.00 -60.00  168
 33  \w     34.00 108.00   0.50    0.20    --  110.00-111.00-120.00  148
 34  \w     33.00 108.00   0.50    0.20    --  110.00-103.00 106.14  150
 35  \w     35.00 124.00   0.50    0.20    --  110.00 -30.00 -60.00  178
 36  \w     69.00 103.00   0.50    0.20    --  110.00 -94.00-150.00   68
 37  \w     57.00 107.00   0.50    0.20    --  110.00 -94.00  30.00  100
 38  \w     54.00  80.00   0.50    0.20    --  110.00 -94.00 -30.00   52
 39  \w    102.00 178.00   0.50    0.20    --  110.00 111.00 150.00  152
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0823467000
_diffrn_orient_matrix_UB_12      -0.0078723000
_diffrn_orient_matrix_UB_13      -0.1498247000
_diffrn_orient_matrix_UB_21      -0.1323986000
_diffrn_orient_matrix_UB_22      -0.0800189000
_diffrn_orient_matrix_UB_23      0.0370445000
_diffrn_orient_matrix_UB_31      -0.0748211000
_diffrn_orient_matrix_UB_32      0.1436483000
_diffrn_orient_matrix_UB_33      0.0149094000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16835
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.483
_diffrn_reflns_theta_min         4.450
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    15.623
_exptl_absorpt_correction_T_max  0.281
_exptl_absorpt_correction_T_min  0.033
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.68a (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    2.072
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         2.630
_refine_diff_density_min         -2.658
_refine_diff_density_rms         0.193
_refine_ls_extinction_coef       0.0065(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3480
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.184
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0312
_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/[\s^2^(Fo^2^)+(0.0532P)^2^+1.6665P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0818
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3469
_reflns_number_total             3480
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc03678e2.cif
_cod_data_source_block           4
_cod_database_code               7129275
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.236
_shelx_estimated_absorpt_t_min   0.082
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C11(H11), C12(H12), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              42974