Palladium-Catalyzed Potassium Enoxyborate Alkylation of Enantiopure Hajos-Parrish Indenone To Construct Rearranged Steroid Ring Systems
Izabella Jastrzebska; Jamie B. Scaglione; Gregory T. DeKoster; Nigam P. Rath; Douglas F. Covey; Journal of Organic Chemistry 72 (2007) 4837–4843; doi:10.1021/jo070530e

data_4023963
_publ_section_title
;
 Palladium-Catalyzed Potassium Enoxyborate Alkylation of Enantiopure
 Hajos-Parrish Indenone To Construct Rearranged Steroid Ring Systems
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4837
_journal_page_last               4843
_journal_paper_doi               10.1021/jo070530e
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C18 H26 O2'
_chemical_formula_weight         274.39
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.592(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.6990(5)
_cell_length_b                   6.4806(3)
_cell_length_c                   11.9721(5)
_cell_measurement_reflns_used    5706
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.99
_cell_volume                     739.69(6)
_computing_cell_refinement       'Bruker APEXII'
_computing_data_collection       'Bruker APEXII'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker-SHELXTL (Sheldrick, 2005)'
_computing_publication_material  'Bruker-SHELXTL (Sheldrick, 2005)'
_computing_structure_refinement  'Bruker-SHELXTL (Sheldrick, 2005)'
_computing_structure_solution    'Bruker-SHELXTL (Sheldrick, 2005)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13823
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9953
_exptl_absorpt_correction_T_min  0.9577
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'sadabs v2006/1'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.5(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         3231
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0491P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0869
_reflns_number_gt                2733
_reflns_number_total             3231
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070530esi20070314_014410.cif
_cod_data_source_block           d2106
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'no' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4023963