Catalytic Enantioselective Diboration of Cyclic Dienes. A Modified Ligand with General Utility
Kai Hong; James P. Morken; Journal of Organic Chemistry 76 (2011) 9102–9108; doi:10.1021/jo201321k

data_4026679
_publ_section_title
;
 Catalytic Enantioselective Diboration of Cyclic Dienes. A Modified Ligand
 with General Utility
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9102
_journal_page_last               9108
_journal_paper_doi               10.1021/jo201321k
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H20 O2'
_chemical_formula_sum            'C12 H20 O2'
_chemical_formula_weight         196.28
_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   difmap
_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            24
_cell_length_a                   10.1084(3)
_cell_length_b                   17.3007(5)
_cell_length_c                   39.0695(13)
_cell_measurement_reflns_used    13731
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      68.52
_cell_measurement_theta_min      3.41
_cell_volume                     6832.6(4)
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker Kappa DUO CCD diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_sigmaI/netI    0.0389
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            45675
_diffrn_reflns_theta_full        68.98
_diffrn_reflns_theta_max         68.98
_diffrn_reflns_theta_min         2.26
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\uS '
_exptl_absorpt_coefficient_mu    0.597
_exptl_absorpt_correction_T_max  0.9882
_exptl_absorpt_correction_T_min  0.8950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G.M. (2008). SADABS v2008/1. Bruker AXS Inc. Madison, WI USA.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_density_method    none
_exptl_crystal_description       plate
_exptl_crystal_F_000             2592
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.11(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     806
_refine_ls_number_reflns         12566
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0540
_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^)+(0.0532P)^2^+3.5178P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1383
_refine_ls_wR_factor_ref         0.1405
_reflns_number_gt                11779
_reflns_number_total             12566
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201321k_si_003.cif
_cod_data_source_block           C12H20O2
_cod_database_code               4026679