Enantioselective reductive multicomponent coupling reactions between isatins and aldehydes.
Horwitz, Matthew A.; Tanaka, Naoya; Yokosaka, Takuya; Uraguchi, Daisuke; Johnson, Jeffrey S.; Ooi, Takashi; Chemical science (Royal Society of Chemistry : 2010) 6 (2015) 6086–6090; doi:10.1039/C5SC02170G

data_1529313
_publ_section_title
;
 Enantioselective reductive multicomponent coupling reactions between
 isatins and aldehydes.
;
_journal_issue                   11
_journal_name_full
'Chemical science (Royal Society of Chemistry : 2010)'
_journal_page_first              6086
_journal_page_last               6090
_journal_paper_doi               10.1039/C5SC02170G
_journal_volume                  6
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H29 Br N O6 P '
_chemical_formula_sum            'C27 H29 Br N O6 P'
_chemical_formula_weight         574.38
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2015-03-23 deposited with the CCDC.
2015-07-23 downloaded from the CCDC.
;
_cell_angle_alpha                91.3040(13)
_cell_angle_beta                 98.3180(17)
_cell_angle_gamma                114.9350(14)
_cell_formula_units_Z            4
_cell_length_a                   10.2391(6)
_cell_length_b                   11.4922(6)
_cell_length_c                   24.9637(12)
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    93.(2)
_cell_measurement_theta_max      28.6816
_cell_measurement_theta_min      2.2483
_cell_volume                     2624.1(2)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker SMART APAXII ULTRA'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XSHELL V6.3.1 (Bruker AXS)'
_computing_publication_material  'Generate Report (Bruker AXS)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0812
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            17679
_diffrn_reflns_theta_full        24.96
_diffrn_reflns_theta_max         24.96
_diffrn_reflns_theta_min         2.20
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    1.670
_exptl_absorpt_correction_T_max  0.875
_exptl_absorpt_correction_T_min  0.733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.955
_refine_diff_density_min         -0.754
_refine_ls_abs_structure_details
;
Flack x determined using 3874 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.065(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1313
_refine_ls_number_reflns         13136
_refine_ls_number_restraints     1803
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0466P)^2^+1.8490P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1249
_reflns_number_gt                12143
_reflns_number_total             13136
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5sc02170g2.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 1529313.cif.'
_cod_original_formula_sum        'C27 H29 Br N O6 P '
_cod_database_code               1529313
_shelx_res_checksum              99652
_shelx_hkl_checksum              21163