The use of symmetry in enantioselective synthesis: Four pairs of chrysene enantiomers prepared from 19-nortestosterone
Stastna, Eva; Rath, Nigam P.; Covey, Douglas F.; Organic & Biomolecular Chemistry 9 (2011) 4685–; doi:10.1039/c1ob05385j

data_7151893
_publ_section_title
;
 The use of symmetry in enantioselective synthesis: Four pairs of
 chrysene enantiomers prepared from 19-nortestosterone
;
_journal_issue                   12
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              4685
_journal_paper_doi               10.1039/c1ob05385j
_journal_volume                  9
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H31 Br O3'
_chemical_formula_sum            'C25 H31 Br O3'
_chemical_formula_weight         459.41
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3869(6)
_cell_length_b                   13.1736(7)
_cell_length_c                   15.8519(8)
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.06
_cell_measurement_theta_min      2.50
_cell_volume                     2169.1(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0152
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            104988
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         31.10
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    1.919
_exptl_absorpt_correction_T_max  0.6910
_exptl_absorpt_correction_T_min  0.6518
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'sadabs v2008/1'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.007(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     386
_refine_ls_number_reflns         6969
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0236
_refine_ls_R_factor_gt           0.0205
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0308P)^2^+0.2191P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0488
_refine_ls_wR_factor_ref         0.0500
_reflns_number_gt                6568
_reflns_number_total             6969
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob05385j.txt
_cod_data_source_block           c23310
_cod_depositor_comments
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The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 1555 2011-01-17 13:19:09Z 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      P2(1)2(1)2(1)
_cod_database_code               7151893