Enantioselective direct Michael addition of cyanohydrin ether derivatives to enones catalyzed by chiral bis(guanidino)iminophosphorane organosuperbase.
Das, Saikat; Kondoh, Azusa; Terada, Masahiro; Chemical science 14 (2023) 3154–3159; doi:10.1039/d2sc07065k

data_1568381
_publ_section_title
;
 Enantioselective direct Michael addition of cyanohydrin ether derivatives
 to enones catalyzed by chiral bis(guanidino)iminophosphorane
 organosuperbase.
;
_journal_issue                   12
_journal_name_full               'Chemical science'
_journal_page_first              3154
_journal_page_last               3159
_journal_paper_doi               10.1039/d2sc07065k
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_sum            'C34 H26 Cl N O2'
_chemical_formula_weight         516.01
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-04-08 deposited with the CCDC.	2023-01-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.638(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2214(5)
_cell_length_b                   28.506(2)
_cell_length_c                   13.0812(9)
_cell_measurement_reflns_used    9888
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      26.15
_cell_measurement_theta_min      2.65
_cell_volume                     2690.0(3)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS Inc., 2017)'
_computing_data_collection
'Bruker Instrument Service V6.2.14 (Bruker AXS Inc., 2018)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle)'
_computing_publication_material
'APEX3 software package (Bruker AXS Inc., 2018)'
_computing_structure_refinement  'SHELXL-2018 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0(5)
_diffrn_detector_area_resol_mean 7.37
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Incoatec Helios multilayer confocal mirror'
_diffrn_radiation_source         'micro focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            38258
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.414
_diffrn_reflns_theta_min         2.114
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.521
_exptl_crystal_size_mid          0.282
_exptl_crystal_size_min          0.138
_refine_diff_density_max         0.933
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details
;
 Flack x determined using 3961 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     685
_refine_ls_number_reflns         10240
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0681
_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^)+(0.0899P)^2^+3.9221P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1756
_refine_ls_wR_factor_ref         0.1777
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_full    0.910
_reflns_Friedel_fraction_max     0.866
_reflns_number_gt                9767
_reflns_number_total             10240
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc07065k2.cif
_cod_data_source_block           p21_a
_cod_depositor_comments          'Adding full bibliography for 1568381.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1568381
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.915
_shelx_estimated_absorpt_t_max   0.976
_shelx_res_checksum              75627