Substrate-directed stereoselectivity in vicinal diamine-catalyzed synthesis of warfarin.
Kim, Hyunwoo; Yen, Cindy; Preston, Philippa; Chin, Jik; Organic letters 8 (2006) 5239–5242; doi:10.1021/ol062000v

data_1506240
_publ_section_title
;
 Substrate-directed stereoselectivity in vicinal diamine-catalyzed
 synthesis of warfarin.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5239
_journal_page_last               5242
_journal_paper_doi               10.1021/ol062000v
_journal_volume                  8
_journal_year                    2006
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C40 H32 N2'
_chemical_formula_sum            'C40 H32 N2'
_chemical_formula_weight         540.68
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 104.949(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   36.957(3)
_cell_length_b                   9.8273(9)
_cell_length_c                   16.7524(17)
_cell_measurement_reflns_used    3830
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      57.17
_cell_measurement_theta_min      2.48
_cell_volume                     5878.3(9)
_computing_cell_refinement       'SMART (Bruker, 2003b)'
_computing_data_collection       'SMART (Bruker, 2003b)'
_computing_data_reduction        'SAINT (Bruker, 2003a)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'UdMX (local program)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.949
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'Bruker Smart 6000'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'Montel 200 optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.093
_diffrn_reflns_av_sigmaI/netI    0.1623
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            38071
_diffrn_reflns_theta_full        68.56
_diffrn_reflns_theta_max         68.56
_diffrn_reflns_theta_min         2.47
_diffrn_standards_decay_%        -0.21
_diffrn_standards_interval_time  1440
_diffrn_standards_number         84
_exptl_absorpt_coefficient_mu    0.539
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.2100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick,2004)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2288
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       0.00064(12)
_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   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         5139
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1834
_refine_ls_R_factor_gt           0.0836
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1030P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1979
_refine_ls_wR_factor_ref         0.2497
_reflns_number_gt                2243
_reflns_number_total             5139
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol062000vsi20060816_094738.cif
_cod_data_source_block           lough6
_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.

'_geom_bond_publ_flag' value 'Y' changed to 'y'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (47
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (62
times).

'_geom_torsion_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (84 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1506240