Enantioselective rhodium-catalyzed addition of arylboronic acids to aldehydes using chiral spiro monophosphite ligands.
Duan, Hai-Feng; Xie, Jian-Hua; Shi, Wen-Jian; Zhang, Qi; Zhou, Qi-Lin; Organic letters 8 (2006) 1479–1481; doi:10.1021/ol060360c

data_1505933
_publ_section_title
;
 Enantioselective rhodium-catalyzed addition of arylboronic acids to
 aldehydes using chiral spiro monophosphite ligands.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1479
_journal_page_last               1481
_journal_paper_doi               10.1021/ol060360c
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C55.5 H53 B Cl3 F4 O6 P2 Rh'
_chemical_formula_weight         1173.99
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 92.150(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   15.362(2)
_cell_length_b                   10.6888(14)
_cell_length_c                   16.338(2)
_cell_measurement_reflns_used    4450
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      23.02
_cell_measurement_theta_min      2.32
_cell_volume                     2680.8(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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      294(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0821
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15197
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    0.591
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.771606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1202
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.713
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     667
_refine_ls_number_reflns         10282
_refine_ls_number_restraints     65
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0880
_refine_ls_R_factor_gt           0.0494
_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^)+(0.0650P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1320
_reflns_number_gt                7279
_reflns_number_total             10282
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol060360csi20060224_104709.cif
_cod_data_source_block           050428c
_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.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN'
changed to 'multi-scan' 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_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' 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_cell_volume        2680.7(6)
_cod_original_sg_symbol_H-M      P2(1)
_cod_original_formula_sum        'C55.50 H53 B Cl3 F4 O6 P2 Rh'
_cod_database_code               1505933