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_7129277
_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         'C22 H16 Cl N2 O4 Re'
_chemical_formula_sum            'C22 H16 Cl N2 O4 Re'
_chemical_formula_weight         594.02
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-04-09
_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
_cell_angle_beta                 95.3950(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.39430(10)
_cell_length_b                   10.47450(10)
_cell_length_c                   23.0911(3)
_cell_measurement_reflns_used    16650
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      76.1410
_cell_measurement_theta_min      3.8250
_cell_volume                     2021.32(4)
_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                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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   -115.00 -20.60   0.80    1.00    --  -42.49 -37.00 150.00  118
  2  \w   -115.00 -20.60   0.80    1.00    --  -42.49 -37.00-120.00  118
  3  \w    -69.00  27.00   0.80    1.00    --  -42.49  57.00  30.00  120
  4  \w    -30.00  64.40   0.80    1.00    --   42.49 -37.00  90.00  118
  5  \w     40.00 136.00   0.80    1.00    --  111.00 -51.00-149.98  120
  6  \w     87.00 177.40   0.80    1.00    --  111.00  30.00-120.00  113
  7  \w     36.00 134.40   0.80    1.00    --  111.00 -30.00   0.00  123
  8  \w     84.00 178.40   0.80    1.00    --  111.00  60.00 -63.09  118
  9  \w     36.00 134.40   0.80    1.00    --  111.00 -30.00-150.00  123
 10  \w     41.00 137.00   0.80    1.00    --  111.00 -54.00  62.12  120
 11  \w     87.00 177.40   0.80    1.00    --  111.00  45.00  90.00  113
 12  \w     87.00 177.40   0.80    1.00    --  111.00  45.00 150.00  113
 13  \w     41.00 137.80   0.80    1.00    --  111.00 -58.00 144.37  121
 14  \w   -113.00 -17.00   0.80    1.00    --  -42.49 -57.00   0.00  120
 15  \w   -113.00 -17.00   0.80    1.00    --  -42.49 -57.00  60.00  120
 16  \w    -28.00  68.00   0.80    1.00    --   42.49 -57.00-150.00  120
 17  \w     85.00 134.60   0.80    1.00    --  111.00  55.00-179.55   62
 18  \w     41.00 138.60   0.80    1.00    --  111.00 -60.00 -35.45  122
 19  \w     87.00 177.40   0.80    1.00    --  111.00  30.00  30.00  113
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1386085000
_diffrn_orient_matrix_UB_12      0.0794592000
_diffrn_orient_matrix_UB_13      0.0300423000
_diffrn_orient_matrix_UB_21      0.1207745000
_diffrn_orient_matrix_UB_22      -0.0800142000
_diffrn_orient_matrix_UB_23      -0.0308688000
_diffrn_orient_matrix_UB_31      -0.0142638000
_diffrn_orient_matrix_UB_32      0.0943919000
_diffrn_orient_matrix_UB_33      -0.0513234000
_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  0.0282
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            20066
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.491
_diffrn_reflns_theta_min         3.846
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    13.257
_exptl_absorpt_correction_T_max  0.397
_exptl_absorpt_correction_T_min  0.026
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.68a (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    1.952
_exptl_crystal_description       prism
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.870
_refine_diff_density_min         -0.608
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       0.00237(5)
_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   1.223
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4135
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.223
_refine_ls_R_factor_all          0.0211
_refine_ls_R_factor_gt           0.0210
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0238P)^2^+2.5431P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0534
_refine_ls_wR_factor_ref         0.0534
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4129
_reflns_number_total             4135
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc03678e2.cif
_cod_data_source_block           6
_cod_database_code               7129277
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.258
_shelx_estimated_absorpt_t_min   0.059
_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), C19(H19), C20(H20),
 C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_shelx_res_checksum              99994