Synthesis and Biological Evaluations of Electrophilic Steroids Inspired by the Taccalonolides
Clanton, Nicholas A.; Hastings, Shayne D.; Foultz, Griffin B.; Contreras, Julie A.; Yee, Samantha S.; Arman, Hadi D.; Risinger, April L.; Frantz, Doug E.; ACS Medicinal Chemistry Letters  (2020) –; doi:10.1021/acsmedchemlett.0c00534

data_4518257
_publ_section_title
;
 Synthesis and Biological Evaluations of Electrophilic Steroids Inspired
 by the Taccalonolides
;
_journal_name_full               'ACS Medicinal Chemistry Letters'
_journal_paper_doi               10.1021/acsmedchemlett.0c00534
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C19 H26 O2'
_chemical_formula_sum            'C19 H26 O2'
_chemical_formula_weight         286.40
_space_group_crystal_system      tetragonal
_space_group_IT_number           76
_space_group_name_Hall           'P 4w'
_space_group_name_H-M_alt        'P 41'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1412(2)
_cell_length_b                   9.1412(2)
_cell_length_c                   18.5205(6)
_cell_measurement_reflns_used    4956
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      28.8380
_cell_measurement_theta_min      3.1090
_cell_volume                     1547.60(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      98(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -97.00  20.00   1.00   25.00    --   -7.70 -30.00 -36.00  117
  2  \w    -85.00  26.00   1.00   25.00    --    4.20 -38.00  90.00  111
  3  \w    -32.00  82.00   1.00   25.00    --   -7.70  38.00-120.00  114
  4  \w    -45.00 -20.00   1.00   25.00    --   -7.70  19.00  30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0072655000
_diffrn_orient_matrix_UB_12      0.0740227000
_diffrn_orient_matrix_UB_13      0.0108797000
_diffrn_orient_matrix_UB_21      0.0734001000
_diffrn_orient_matrix_UB_22      -0.0134686000
_diffrn_orient_matrix_UB_23      0.0105328000
_diffrn_orient_matrix_UB_31      0.0241842000
_diffrn_orient_matrix_UB_32      0.0188382000
_diffrn_orient_matrix_UB_33      -0.0351789000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16652
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_min         2.485
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;

;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3010
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0446
_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^)+(0.0380P)^2^+1.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.0990
_reflns_Friedel_coverage         0.927
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                2975
_reflns_number_total             3010
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ml0c00534_si_004.cif
_cod_data_source_block           cd1830
_cod_original_cell_volume        1547.60(8)
_cod_database_code               4518257
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C19H26O2
_chemical_oxdiff_usercomment     NAC-224-90
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.975
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15), C6(H6), C17(H17), C1(H1), C16(H16), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C4(H4A,H4B), C13(H13A,H13B), C5(H5A,H5B), C8(H8A,H8B),
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C18(H18A,H18B,H18C)
;
_olex2_exptl_crystal_mounting_method 'nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.073
_oxdiff_exptl_absorpt_empirical_full_min 0.966