Asymmetric hydrogenation of unsaturated ureas with the BIPI ligands.
Busacca, Carl A.; Lorenz, Jon C.; Grinberg, Nelu; Haddad, Nizar; Lee, Heewon; Li, Zhibin; Liang, Mary; Reeves, Diana; Saha, Anjan; Varsolona, Rich; Senanayake, Chris H.; Organic letters 10 (2008) 341–344; doi:10.1021/ol7028542

data_1504519
_publ_section_title
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 Asymmetric hydrogenation of unsaturated ureas with the BIPI ligands.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              341
_journal_page_last               344
_journal_paper_doi               10.1021/ol7028542
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C33 H43 B N2 P, Cl, C2 H3 N'
_chemical_formula_sum            'C35 H46 B Cl N3 P'
_chemical_formula_weight         585.98
_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                 98.6390(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1636(2)
_cell_length_b                   12.5300(2)
_cell_length_c                   26.5187(5)
_cell_measurement_reflns_used    16746
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      71.9
_cell_measurement_theta_min      6.75
_cell_volume                     3338.84(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 0.10
_diffrn_measured_fraction_theta_full 0.905
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measurement_device_type  'Rigaku RAXIS SPIDER'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0144
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            17515
_diffrn_reflns_theta_full        71.96
_diffrn_reflns_theta_max         71.96
_diffrn_reflns_theta_min         6.75
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    1.660
_exptl_absorpt_correction_T_max  0.8257
_exptl_absorpt_correction_T_min  0.7115
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.003(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     743
_refine_ls_number_reflns         9096
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0304
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0584P)^2^+0.2380P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0824
_reflns_number_gt                8734
_reflns_number_total             9096
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7028542-file003.cif
_cod_data_source_block           shelxl
_cod_database_code               1504519