1,3-Diaxially Substituted trans-Decalins: Potential Nonsteroidal Human Progesterone Receptor Inhibitors
Ze Li; E. Blake Watkins; Hua Liu; Amar G. Chittiboyina; Paulo B. Carvalho; Mitchell A. Avery; Journal of Organic Chemistry 73 (2008) 7764–7767; doi:10.1021/jo800947m

data_4023700
_publ_contact_author_address
;
University of Mississippi
Department of Medicinal Chemistry
417 Faser Hall
University, MS 38677

National Center for Natural Products Research,Research Institute of
Pharmaceutical Sciences, School of Pharmacy, University of Mississippi,
University, MS 38677, USA

and

Department of Chemistry and Biochemistry
University of Mississippi
University, MS 38677
;
_publ_contact_author_email       mavery@olemiss.edu
_publ_contact_author_fax         '662-915-5638 '
_publ_contact_author_name        'Mitchell A. Avery'
_publ_contact_author_phone       662-915-5879
_publ_section_title
;
 1,3-Diaxially Substituted trans-Decalins: Potential
 Nonsteroidal Human Progesterone Receptor Inhibitors
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7764
_journal_page_last               7767
_journal_paper_doi               10.1021/jo800947m
_journal_volume                  73
_journal_year                    2008
_chemical_compound_source
'Synthesized as an intermediate for Compound 1'
_chemical_formula_moiety         'C22 H27 Br N O6 S'
_chemical_formula_sum            'C22 H27 Br N O6 S'
_chemical_formula_weight         513.42
_chemical_name_systematic
;(4aR,5aS,8S,9S,9aS,10aR)-9-(2-bromo-5-methoxycyclohexylthio)-8-
(methoxymethoxy)-4a-methyldecahydro-2H-naphtho[2,3-e][1,3]oxazine-2,4(3H)-dione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2008-02-20 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.841(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2085(4)
_cell_length_b                   19.7308(6)
_cell_length_c                   11.4516(3)
_cell_measurement_reflns_used    9082
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      69.34
_cell_measurement_theta_min      4.47
_cell_volume                     2301.42(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17567
_diffrn_reflns_theta_full        69.42
_diffrn_reflns_theta_max         69.42
_diffrn_reflns_theta_min         4.47
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Siemens KFF Cu 2 K90'
_exptl_absorpt_coefficient_mu    3.609
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Cubic
_exptl_crystal_F_000             1088
_exptl_crystal_recrystallization_method
'from a solution in Ethyl Acetate/Hexanes 1:9'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.00245(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4181
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0330
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0479P)^2^+1.0039P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.1022
_reflns_number_gt                3571
_reflns_number_total             4181
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800947m-file006.cif
_cod_data_source_block           pr_cry
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4023700