Synthesis and biological evaluation of FJ-809, a compound originally described as MIM1 and an inhibitor of the anti-apoptotic protein Mcl-1
Justaud, Frédéric; Paysant, Hippolyte; Weiswald, Louis Bastien; Jebahi, Abdelghani; Jouanne, Marie; Elie, Nicolas; Voisin-Chiret, Anne Sophie; Roisnel, Thierry; Orione, Clément; Levoin, Nicolas; Poulain, Laurent; Grée, René; New Journal of Chemistry 46 (2022) 9119–9127; doi:10.1039/D1NJ05987D

data_7061459
_publ_section_title
;
 Synthesis and biological evaluation of FJ-809, a compound originally
 described as MIM1 and an inhibitor of the anti-apoptotic protein Mcl-1
;
_journal_issue                   19
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              9119
_journal_page_last               9127
_journal_paper_doi               10.1039/D1NJ05987D
_journal_volume                  46
_journal_year                    2022
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C17 H20 N4 O2 S'
_chemical_formula_sum            'C17 H20 N4 O2 S'
_chemical_formula_weight         344.43
_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   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2021-11-22 deposited with the CCDC.	2022-04-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.538(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1420(5)
_cell_length_b                   22.7420(18)
_cell_length_c                   12.2786(8)
_cell_measurement_reflns_used    9951
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.5079
_cell_measurement_theta_min      3.1639
_cell_measurement_wavelength     0.71073
_cell_volume                     1703.9(2)
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics
'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2019)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (G. Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_orient_matrix_UB_11      -0.1270089
_diffrn_orient_matrix_UB_12      0.0212730
_diffrn_orient_matrix_UB_13      0.0258783
_diffrn_orient_matrix_UB_21      -0.0842260
_diffrn_orient_matrix_UB_22      -0.0376788
_diffrn_orient_matrix_UB_23      -0.0015452
_diffrn_orient_matrix_UB_31      0.0602580
_diffrn_orient_matrix_UB_32      -0.0078275
_diffrn_orient_matrix_UB_33      0.0777684
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0775
_diffrn_reflns_av_unetI/netI     0.0634
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17354
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.515
_diffrn_reflns_theta_min         1.894
_diffrn_source_current           1.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.422
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       stick
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.070
_refine_diff_density_max         1.179
_refine_diff_density_min         -1.014
_refine_diff_density_rms         0.143
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3887
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.156
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0829
_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^)+(0.1403P)^2^+0.4782P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2065
_refine_ls_wR_factor_ref         0.2163
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3311
_reflns_number_total             3887
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1nj05987d2.cif
_cod_data_source_block           JF766
_cod_depositor_comments          'Adding full bibliography for 7061459.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7061459
_shelx_res_checksum              89044