Structure–Activity Relationships for the Marine Natural Product Sintokamides: Androgen Receptor N-Terminus Antagonists of Interest for Treatment of Metastatic Castration-Resistant Prostate Cancer
Yan, Luping; Banuelos, Carmen A.; Mawji, Nasrin R.; Patrick, Brian O.; Sadar, Marianne D.; Andersen, Raymond J.; Journal of Natural Products  (2020) –; doi:10.1021/acs.jnatprod.0c00921

data_1559434
_publ_section_title
;
 Structure--Activity Relationships for the Marine Natural Product
 Sintokamides: Androgen Receptor N-Terminus Antagonists of Interest for
 Treatment of Metastatic Castration-Resistant Prostate Cancer
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.0c00921
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C9 H15 Cl3 N2 O S'
_chemical_formula_weight         305.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.123(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.8041(9)
_cell_length_b                   9.6514(14)
_cell_length_c                   12.3924(18)
_cell_measurement_reflns_used    9969
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      30.03
_cell_measurement_theta_min      2.70
_cell_volume                     678.71(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    Olex2
_computing_publication_material  Olex2
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    XT
_diffrn_ambient_temperature      90(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker-Nonius APEXII CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'TRIUMPH curved-crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_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            13540
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.026
_diffrn_reflns_theta_min         2.698
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.811
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_correction_T_min  0.750
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_description       plate
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1784 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.021(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         3946
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0201
_refine_ls_R_factor_gt           0.0191
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0221P)^2^+0.1040P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0465
_refine_ls_wR_factor_ref         0.0471
_reflns_Friedel_coverage         0.892
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                3852
_reflns_number_total             3946
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00921_si_004.cif
_cod_data_source_block           ra098
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1559434
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              80034
_shelx_hkl_checksum              5108