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_7158331
_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_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C23 H20 N3 O S, Br'
_chemical_formula_sum            'C23 H20 Br N3 O S'
_chemical_formula_weight         466.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
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_cell_length_b                   40.014(4)
_cell_length_c                   9.3291(11)
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_cell_measurement_temperature    150
_cell_measurement_theta_max      27.4664
_cell_measurement_theta_min      2.3894
_cell_measurement_wavelength     0.71073
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_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)'
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_diffrn_detector                 '(CMOS) PHOTON 100'
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_diffrn_measured_fraction_theta_max 0.998
_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
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_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -31
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_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
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_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.503
_diffrn_reflns_theta_min         2.389
_diffrn_source_current           1.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.897
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_exptl_absorpt_correction_T_min  0.548
_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    1.348
_exptl_crystal_description       prism
_exptl_crystal_F_000             3808
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_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.780
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.026(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         5182
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0276
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0239P)^2^+15.2430P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0655
_refine_ls_wR_factor_ref         0.0664
_reflns_Friedel_coverage         0.855
_reflns_Friedel_fraction_full    0.961
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                4943
_reflns_number_total             5182
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1ob01521d2.cif
_cod_data_source_block           RG2
_cod_depositor_comments
'Adding full bibliography for 7158330--7158332.cif.'
_cod_original_cell_volume        9193.2(18)
_cod_database_code               7158331
_shelx_res_checksum              94004
_shelx_fab_checksum              7025