Enantioselective synthesis of biphenols from 1,4-diketones by traceless central-to-axial chirality exchange.
Guo, Fenghai; Konkol, Leah C.; Thomson, Regan J.; Journal of the American Chemical Society 133 (2011) 18–20; doi:10.1021/ja108717r

data_4101609
_publ_section_title
;
 Enantioselective synthesis of biphenols from 1,4-diketones by traceless
 central-to-axial chirality exchange.
;
_journal_issue                   1
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              18
_journal_page_last               20
_journal_paper_doi               10.1021/ja108717r
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C17 H18 Cl2 O4'
_chemical_formula_weight         359.24
_chemical_name_systematic
; 
 ? 
;
_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                   8.1103(3)
_cell_length_b                   12.5967(5)
_cell_length_c                   16.9792(6)
_cell_measurement_reflns_used    5043
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      64.10
_cell_measurement_theta_min      4.37
_cell_volume                     1734.65(11)
_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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0849
_diffrn_reflns_av_sigmaI/netI    0.0648
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11346
_diffrn_reflns_theta_full        64.55
_diffrn_reflns_theta_max         64.55
_diffrn_reflns_theta_min         4.37
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.493
_exptl_absorpt_correction_T_max  0.8178
_exptl_absorpt_correction_T_min  0.2099
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   face-indexed
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.583
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         2858
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0492
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0794P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1242
_refine_ls_wR_factor_ref         0.1298
_reflns_number_gt                2391
_reflns_number_total             2858
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja108717r_si_005.cif
_cod_data_source_block           n0735abs
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1673 2011-04-08 12:14:43Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4101609