Structural revision of the Mcl-1 inhibitor MIM1: synthesis and biological studies on ovarian cancer cells with evaluation of designed analogues.
Paysant, Hippolyte; Hedir, Siham; Justaud, Frédéric; Weiswald, Louis Bastien; El Dine, Assaad Nasr; Soulieman, Ali; Hachem, Ali; Elie, Nicolas; Brotin, Emilie; Denoyelle, Christophe; Bignon, Jérôme; Roussi, Fanny; Jouanne, Marie; Tasseau, Olivier; Roisnel, Thierry; Voisin-Chiret, Anne Sophie; Grée, René; Levoin, Nicolas; Poulain, Laurent; Organic & biomolecular chemistry 19 (2021) 8968–8987; doi:10.1039/d1ob01521d

data_7158330
_publ_section_title
;
 Structural revision of the Mcl-1 inhibitor MIM1: synthesis and biological
 studies on ovarian cancer cells with evaluation of designed analogues.
;
_journal_issue                   41
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8968
_journal_page_last               8987
_journal_paper_doi               10.1039/d1ob01521d
_journal_volume                  19
_journal_year                    2021
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C23 H20 N3 S, Br, H2 O'
_chemical_formula_sum            'C23 H22 Br N3 O S'
_chemical_formula_weight         468.40
_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
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2020-05-29 deposited with the CCDC.	2021-09-16 downloaded from the CCDC.
;
_cell_angle_alpha                80.956(4)
_cell_angle_beta                 81.422(4)
_cell_angle_gamma                65.230(4)
_cell_formula_units_Z            2
_cell_length_a                   9.0870(10)
_cell_length_b                   10.0635(13)
_cell_length_c                   13.3909(17)
_cell_measurement_reflns_used    9840
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.6809
_cell_measurement_theta_min      2.2413
_cell_measurement_wavelength     0.71073
_cell_volume                     1093.3(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 0.984
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_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  0.0365
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21379
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.539
_diffrn_reflns_theta_min         2.241
_diffrn_source_current           1.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.994
_exptl_absorpt_correction_T_max  0.772
_exptl_absorpt_correction_T_min  0.592
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_description       prism
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4926
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0264
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0082P)^2^+1.2468P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0557
_refine_ls_wR_factor_ref         0.0595
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4380
_reflns_number_total             4926
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1ob01521d2.cif
_cod_data_source_block           RG13
_cod_depositor_comments
'Adding full bibliography for 7158330--7158332.cif.'
_cod_database_code               7158330
_shelx_res_checksum              35393