Characterization of Conformationally Constrained Benzanilide Scaffolds for Potent and Selective HDAC8 Targeting.
Hassan, Muhammad Murtaza; Israelian, Johan; Nawar, Nabanita; Ganda, Giovanni; Manaswiyoungkul, Pimyupa; Raouf, Yasir; Armstrong, David; Sedighi, Abootaleb; Olaoye, Olasunkanmi O.; Erdogan, Fettah; Cabral, Aaron D.; Angeles, Fabrizio; Altintas, Rabia; de Araujo, Elvin D.; Gunning, Patrick Thomas; Journal of medicinal chemistry  (2020) –; doi:10.1021/acs.jmedchem.0c01025

data_1558719
_publ_section_title
;
 Characterization of Conformationally Constrained Benzanilide Scaffolds
 for Potent and Selective HDAC8 Targeting.
;
_journal_name_full               'Journal of medicinal chemistry'
_journal_paper_doi               10.1021/acs.jmedchem.0c01025
_journal_year                    2020
_chemical_formula_moiety         'C19 H16 F6 N2 O3'
_chemical_formula_sum            'C19 H16 F6 N2 O3'
_chemical_formula_weight         434.34
_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
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 97.644(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.449(1)
_cell_length_b                   19.3720(18)
_cell_length_c                   21.3178(19)
_cell_measurement_reflns_used    2587
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      64.17
_cell_measurement_theta_min      3.10
_cell_volume                     3867.5(6)
_computing_cell_refinement       APEX3
_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015a)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.4059
_diffrn_reflns_av_unetI/netI     0.2581
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            47568
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.932
_diffrn_reflns_theta_min         3.095
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_exptl_absorpt_coefficient_mu    1.234
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.4905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_description       needle
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.573
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.149
_refine_ls_extinction_coef       0.0103(10)
_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   0.964
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     546
_refine_ls_number_reflns         6947
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.964
_refine_ls_R_factor_all          0.2092
_refine_ls_R_factor_gt           0.1136
_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^)+(0.1516P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2670
_refine_ls_wR_factor_ref         0.3501
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3129
_reflns_number_total             6947
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jm0c01025_si_004.cif
_cod_data_source_block           d19128_a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1558719
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.550
_shelx_estimated_absorpt_t_max   0.976
_shelx_res_checksum              98564
_shelx_hkl_checksum              25512