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_4101608
_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            'C32 H34 O8'
_chemical_formula_weight         546.59
_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            8
_cell_length_a                   8.0008(2)
_cell_length_b                   19.2436(4)
_cell_length_c                   36.6855(8)
_cell_measurement_reflns_used    9968
_cell_measurement_temperature    84(2)
_cell_measurement_theta_max      64.34
_cell_measurement_theta_min      3.33
_cell_volume                     5648.3(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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      84(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_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  0.1064
_diffrn_reflns_av_sigmaI/netI    0.0549
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            61040
_diffrn_reflns_theta_full        64.87
_diffrn_reflns_theta_max         64.87
_diffrn_reflns_theta_min         2.41
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.755
_exptl_absorpt_correction_T_max  0.8198
_exptl_absorpt_correction_T_min  0.6806
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   face-indexed
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2320
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.105
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     737
_refine_ls_number_reflns         9275
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.1094
_refine_ls_R_factor_gt           0.0971
_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^)+(0.1257P)^2^+10.7230P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2532
_refine_ls_wR_factor_ref         0.2642
_reflns_number_gt                7948
_reflns_number_total             9275
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja108717r_si_004.cif
_cod_data_source_block           n0590cabs
_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               4101608