BINOL derivatives-catalysed enantioselective allylboration of isatins: application to the synthesis of (R)-chimonamidine.
Braire, Julien; Dorcet, Vincent; Vidal, Joëlle; Lalli, Claudia; Carreaux, François; Organic & biomolecular chemistry 18 (2020) 6042–6046; doi:10.1039/d0ob01386b

data_7157630
_publ_section_title
;
 BINOL derivatives-catalysed enantioselective allylboration of isatins:
 application to the synthesis of (R)-chimonamidine.
;
_journal_issue                   31
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6042
_journal_page_last               6046
_journal_paper_doi               10.1039/d0ob01386b
_journal_volume                  18
_journal_year                    2020
_chemical_absolute_configuration rm/ad/rmad/syn/unk/.
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C12 H13 N O2'
_chemical_formula_sum            'C12 H13 N O2'
_chemical_formula_weight         203.23
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2020-02-17 deposited with the CCDC.	2020-07-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3607(8)
_cell_length_b                   8.0406(11)
_cell_length_c                   17.598(2)
_cell_measurement_reflns_used    2143
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      74.4807
_cell_measurement_theta_min      5.0265
_cell_measurement_wavelength     1.54184
_cell_volume                     1041.5(2)
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics
'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2019)'
_computing_structure_refinement  'SHELXL-2017_1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_orient_matrix_UB_11      0.0216660
_diffrn_orient_matrix_UB_12      0.0739528
_diffrn_orient_matrix_UB_13      -0.0447802
_diffrn_orient_matrix_UB_21      0.0210248
_diffrn_orient_matrix_UB_22      -0.0999229
_diffrn_orient_matrix_UB_23      -0.0326705
_diffrn_orient_matrix_UB_31      -0.1324593
_diffrn_orient_matrix_UB_32      -0.0037641
_diffrn_orient_matrix_UB_33      -0.0125102
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_unetI/netI     0.0766
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4737
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.603
_diffrn_reflns_theta_min         6.519
_diffrn_source_current           1.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.718
_exptl_absorpt_correction_T_max  0.854
_exptl_absorpt_correction_T_min  0.693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       prism
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details
;
Flack x determined using 415 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_extinction_coef       0.023(4)
_refine_ls_extinction_method     'SHELXL-2017_1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         1990
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1305
_refine_ls_R_factor_gt           0.0830
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0636P)^2^+4.4547P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2006
_refine_ls_wR_factor_ref         0.2428
_reflns_Friedel_coverage         0.635
_reflns_Friedel_fraction_full    0.923
_reflns_Friedel_fraction_max     0.885
_reflns_number_gt                1408
_reflns_number_total             1990
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0ob01386b2.cif
_cod_data_source_block           JBR49P01
_cod_depositor_comments
'Adding full bibliography for 7157629--7157630.cif.'
_cod_database_code               7157630
_shelx_res_checksum              51614
_shelx_hkl_checksum              44844