#------------------------------------------------------------------------------
#$Date: 2021-11-06 22:40:20 +0200 (Sat, 06 Nov 2021) $
#$Revision: 270492 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158330.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7158330
loop_
_publ_author_name
'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'
_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 & 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/[σ²(Fo²)+(0.0082P)²+1.2468P] where P=(Fo²+2Fc²)/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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.20870(5) 0.28554(5) 0.47510(3) 0.01671(9) Uani 1 1 d . . . . .
C1 C 0.1234(2) 0.41346(19) 0.37432(13) 0.0172(3) Uani 1 1 d . . . . .
H1 H 0.012641 0.447525 0.361761 0.021 Uiso 1 1 calc R U . . .
C2 C 0.2300(2) 0.45923(19) 0.31603(13) 0.0151(3) Uani 1 1 d . . . . .
C3 C 0.1957(2) 0.5671(2) 0.22478(13) 0.0169(3) Uani 1 1 d . . . . .
C4 C 0.2876(2) 0.5347(2) 0.13177(14) 0.0230(4) Uani 1 1 d . . . . .
H4 H 0.378800 0.443196 0.126733 0.028 Uiso 1 1 calc R U . . .
C5 C 0.2461(3) 0.6361(2) 0.04657(15) 0.0296(5) Uani 1 1 d . . . . .
H5 H 0.308360 0.613395 -0.016829 0.035 Uiso 1 1 calc R U . . .
C6 C 0.1141(3) 0.7705(2) 0.05350(16) 0.0331(5) Uani 1 1 d . . . . .
H6 H 0.086098 0.839611 -0.004997 0.040 Uiso 1 1 calc R U . . .
C7 C 0.0236(3) 0.8035(2) 0.14558(17) 0.0355(5) Uani 1 1 d . . . . .
H7 H -0.066272 0.895890 0.150509 0.043 Uiso 1 1 calc R U . . .
C8 C 0.0634(2) 0.7021(2) 0.23105(15) 0.0263(4) Uani 1 1 d . . . . .
H8 H 0.000044 0.725107 0.294089 0.032 Uiso 1 1 calc R U . . .
N9 N 0.38740(17) 0.38990(15) 0.35110(11) 0.0135(3) Uani 1 1 d . . . . .
C10 C 0.5257(2) 0.42242(19) 0.30690(12) 0.0137(3) Uani 1 1 d . . . . .
C11 C 0.5200(2) 0.5615(2) 0.30980(14) 0.0184(4) Uani 1 1 d . . . . .
H11 H 0.426776 0.635192 0.340522 0.022 Uiso 1 1 calc R U . . .
C12 C 0.6537(2) 0.5911(2) 0.26681(14) 0.0216(4) Uani 1 1 d . . . . .
H12 H 0.651903 0.685870 0.268044 0.026 Uiso 1 1 calc R U . . .
C13 C 0.7895(2) 0.4830(2) 0.22217(13) 0.0209(4) Uani 1 1 d . . . . .
H13 H 0.879721 0.504297 0.191969 0.025 Uiso 1 1 calc R U . . .
C14 C 0.7936(2) 0.3439(2) 0.22163(14) 0.0213(4) Uani 1 1 d . . . . .
H14 H 0.887724 0.269484 0.192244 0.026 Uiso 1 1 calc R U . . .
C15 C 0.6611(2) 0.3127(2) 0.26380(13) 0.0173(3) Uani 1 1 d . . . . .
H15 H 0.663210 0.217699 0.263085 0.021 Uiso 1 1 calc R U . . .
C16 C 0.3917(2) 0.29708(19) 0.43538(13) 0.0148(3) Uani 1 1 d . . . . .
N17 N 0.52456(19) 0.21804(17) 0.48458(11) 0.0170(3) Uani 1 1 d . . . . .
H17 H 0.612(3) 0.233(2) 0.4737(16) 0.020 Uiso 1 1 d . U . . .
N18 N 0.49790(18) 0.13859(16) 0.57500(11) 0.0161(3) Uani 1 1 d . . . . .
C19 C 0.6235(2) 0.0640(2) 0.62363(14) 0.0189(4) Uani 1 1 d . . . . .
H19 H 0.726990 0.060082 0.594437 0.023 Uiso 1 1 calc R U . . .
C20 C 0.6097(2) -0.01510(19) 0.72351(14) 0.0187(4) Uani 1 1 d . . . . .
C21 C 0.7463(3) -0.0798(3) 0.77823(16) 0.0338(5) Uani 1 1 d . . . . .
H21 H 0.846514 -0.076094 0.748845 0.041 Uiso 1 1 calc R U . . .
C22 C 0.7364(3) -0.1498(3) 0.87558(17) 0.0365(5) Uani 1 1 d . . . . .
H22 H 0.830803 -0.194024 0.911624 0.044 Uiso 1 1 calc R U . . .
C23 C 0.5929(3) -0.1564(2) 0.92102(14) 0.0248(4) Uani 1 1 d . . . . .
C24 C 0.4569(3) -0.0924(2) 0.86570(15) 0.0245(4) Uani 1 1 d . . . . .
H24 H 0.357072 -0.096880 0.895252 0.029 Uiso 1 1 calc R U . . .
C25 C 0.4646(2) -0.0223(2) 0.76826(14) 0.0213(4) Uani 1 1 d . . . . .
H25 H 0.370388 0.020794 0.732055 0.026 Uiso 1 1 calc R U . . .
C26 C 0.5833(3) -0.2303(2) 1.02752(15) 0.0337(5) Uani 1 1 d . . . . .
H26A H 0.590548 -0.329619 1.024635 0.051 Uiso 1 1 calc R U . . .
H26B H 0.479675 -0.172792 1.064394 0.051 Uiso 1 1 calc R U . . .
H26C H 0.673545 -0.236583 1.062672 0.051 Uiso 1 1 calc R U . . .
Br1 Br 0.84394(2) 0.28265(2) 0.49974(2) 0.02010(6) Uani 1 1 d . . . . .
O1W O 0.9152(2) 0.00954(19) 0.35171(14) 0.0412(4) Uani 1 1 d . . . . .
H1WA H 0.901(3) 0.081(3) 0.386(2) 0.049 Uiso 1 1 d . U . . .
H1WB H 0.973(4) -0.068(3) 0.388(2) 0.049 Uiso 1 1 d . U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 S1 C1 89.38(8) . . ?
C2 C1 S1 113.01(13) . . ?
C2 C1 H1 123.5 . . ?
S1 C1 H1 123.5 . . ?
C1 C2 N9 111.96(15) . . ?
C1 C2 C3 126.23(16) . . ?
N9 C2 C3 121.80(15) . . ?
C8 C3 C4 119.25(17) . . ?
C8 C3 C2 118.86(16) . . ?
C4 C3 C2 121.83(16) . . ?
C5 C4 C3 120.04(18) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C6 C5 C4 120.32(19) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C6 C5 119.86(19) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 120.2(2) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C3 120.32(19) . . ?
C7 C8 H8 119.8 . . ?
C3 C8 H8 119.8 . . ?
C16 N9 C2 112.15(14) . . ?
C16 N9 C10 122.98(14) . . ?
C2 N9 C10 124.71(14) . . ?
C15 C10 C11 121.72(17) . . ?
C15 C10 N9 118.93(15) . . ?
C11 C10 N9 119.35(15) . . ?
C10 C11 C12 118.64(17) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
C13 C12 C11 120.40(18) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 119.98(18) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.36(17) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C10 C15 C14 118.89(17) . . ?
C10 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
N17 C16 N9 124.53(16) . . ?
N17 C16 S1 121.97(13) . . ?
N9 C16 S1 113.49(12) . . ?
C16 N17 N18 114.68(15) . . ?
C16 N17 H17 124.0(15) . . ?
N18 N17 H17 118.9(15) . . ?
C19 N18 N17 115.38(15) . . ?
N18 C19 C20 120.84(17) . . ?
N18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C25 C20 C21 118.69(17) . . ?
C25 C20 C19 122.91(16) . . ?
C21 C20 C19 118.33(17) . . ?
C22 C21 C20 120.3(2) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C23 C22 C21 121.52(19) . . ?
C23 C22 H22 119.2 . . ?
C21 C22 H22 119.2 . . ?
C22 C23 C24 117.98(18) . . ?
C22 C23 C26 120.89(19) . . ?
C24 C23 C26 121.1(2) . . ?
C25 C24 C23 121.29(19) . . ?
C25 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C24 C25 C20 120.25(17) . . ?
C24 C25 H25 119.9 . . ?
C20 C25 H25 119.9 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
H1WA O1W H1WB 104(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C16 1.7149(18) . ?
S1 C1 1.7346(18) . ?
C1 C2 1.340(3) . ?
C1 H1 0.9500 . ?
C2 N9 1.419(2) . ?
C2 C3 1.477(2) . ?
C3 C8 1.391(3) . ?
C3 C4 1.395(3) . ?
C4 C5 1.388(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.380(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.389(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
N9 C16 1.341(2) . ?
N9 C10 1.449(2) . ?
C10 C15 1.384(2) . ?
C10 C11 1.385(2) . ?
C11 C12 1.391(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 N17 1.339(2) . ?
N17 N18 1.391(2) . ?
N17 H17 0.86(2) . ?
N18 C19 1.281(2) . ?
C19 C20 1.462(2) . ?
C19 H19 0.9500 . ?
C20 C25 1.391(3) . ?
C20 C21 1.395(3) . ?
C21 C22 1.390(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.379(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.395(3) . ?
C23 C26 1.509(3) . ?
C24 C25 1.389(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
O1W H1WA 0.86(3) . ?
O1W H1WB 0.86(3) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 S1 C1 C2 0.09(14) . . . . ?
S1 C1 C2 N9 0.60(19) . . . . ?
S1 C1 C2 C3 179.91(14) . . . . ?
C1 C2 C3 C8 51.3(3) . . . . ?
N9 C2 C3 C8 -129.51(19) . . . . ?
C1 C2 C3 C4 -125.9(2) . . . . ?
N9 C2 C3 C4 53.3(2) . . . . ?
C8 C3 C4 C5 -0.6(3) . . . . ?
C2 C3 C4 C5 176.59(18) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C7 0.0(3) . . . . ?
C5 C6 C7 C8 -0.6(4) . . . . ?
C6 C7 C8 C3 0.6(4) . . . . ?
C4 C3 C8 C7 0.0(3) . . . . ?
C2 C3 C8 C7 -177.3(2) . . . . ?
C1 C2 N9 C16 -1.2(2) . . . . ?
C3 C2 N9 C16 179.45(15) . . . . ?
C1 C2 N9 C10 -176.66(15) . . . . ?
C3 C2 N9 C10 4.0(2) . . . . ?
C16 N9 C10 C15 68.0(2) . . . . ?
C2 N9 C10 C15 -116.98(18) . . . . ?
C16 N9 C10 C11 -111.25(19) . . . . ?
C2 N9 C10 C11 63.7(2) . . . . ?
C15 C10 C11 C12 0.9(3) . . . . ?
N9 C10 C11 C12 -179.84(15) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
C11 C12 C13 C14 -1.0(3) . . . . ?
C12 C13 C14 C15 1.3(3) . . . . ?
C11 C10 C15 C14 -0.6(3) . . . . ?
N9 C10 C15 C14 -179.89(15) . . . . ?
C13 C14 C15 C10 -0.5(3) . . . . ?
C2 N9 C16 N17 -179.64(16) . . . . ?
C10 N9 C16 N17 -4.1(3) . . . . ?
C2 N9 C16 S1 1.29(18) . . . . ?
C10 N9 C16 S1 176.83(12) . . . . ?
C1 S1 C16 N17 -179.91(16) . . . . ?
C1 S1 C16 N9 -0.80(14) . . . . ?
N9 C16 N17 N18 174.78(15) . . . . ?
S1 C16 N17 N18 -6.2(2) . . . . ?
C16 N17 N18 C19 -179.07(16) . . . . ?
N17 N18 C19 C20 175.21(16) . . . . ?
N18 C19 C20 C25 4.2(3) . . . . ?
N18 C19 C20 C21 -172.48(19) . . . . ?
C25 C20 C21 C22 -0.1(3) . . . . ?
C19 C20 C21 C22 176.8(2) . . . . ?
C20 C21 C22 C23 -0.5(4) . . . . ?
C21 C22 C23 C24 0.9(3) . . . . ?
C21 C22 C23 C26 -178.8(2) . . . . ?
C22 C23 C24 C25 -0.8(3) . . . . ?
C26 C23 C24 C25 178.99(18) . . . . ?
C23 C24 C25 C20 0.2(3) . . . . ?
C21 C20 C25 C24 0.2(3) . . . . ?
C19 C20 C25 C24 -176.48(18) . . . . ?
