N-Heterocyclic carbenes as chiral Brønsted base catalysts: a highly diastereo- and enantioselective 1,6-addition reaction.
Santra, Surojit; Porey, Arka; Jana, Barun; Guin, Joyram; Chemical science 9 (2018) 6446–6450; doi:10.1039/c8sc02138d

data_1549642
_publ_section_title
;
 N-Heterocyclic carbenes as chiral Br\/onsted base catalysts: a highly
 diastereo- and enantioselective 1,6-addition reaction.
;
_journal_issue                   30
_journal_name_full               'Chemical science'
_journal_page_first              6446
_journal_page_last               6450
_journal_paper_doi               10.1039/c8sc02138d
_journal_volume                  9
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C36 H43 N2 O6 S'
_chemical_formula_weight         631.78
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2018-03-21 deposited with the CCDC.
2018-07-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.571(3)
_cell_length_b                   25.090(6)
_cell_length_c                   11.915(4)
_cell_measurement_reflns_used    6658
_cell_measurement_temperature    106(2)
_cell_measurement_theta_max      24.97
_cell_measurement_theta_min      2.36
_cell_volume                     3459.1(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      106(2)
_diffrn_measured_fraction_theta_full 0.882
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1030
_diffrn_reflns_av_unetI/netI     0.1631
_diffrn_reflns_Laue_measured_fraction_full 0.882
_diffrn_reflns_Laue_measured_fraction_max 0.905
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25609
_diffrn_reflns_point_group_measured_fraction_full 0.855
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         2.357
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_description       block
_exptl_crystal_F_000             1348
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_refine_diff_density_max         1.033
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 2015 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.26(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     831
_refine_ls_number_reflns         10699
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.933
_refine_ls_R_factor_all          0.1280
_refine_ls_R_factor_gt           0.0701
_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^)+(0.0655P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1512
_refine_ls_wR_factor_ref         0.1747
_reflns_Friedel_coverage         0.892
_reflns_Friedel_fraction_full    0.827
_reflns_Friedel_fraction_max     0.849
_reflns_number_gt                6162
_reflns_number_total             10699
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc02138d2.cif
_cod_data_source_block           TEST1_a
_cod_depositor_comments
'Adding full bibliography for 1549640--1549642.cif.'
_cod_original_cell_volume        3459.0(17)
_cod_database_code               1549642
_shelx_estimated_absorpt_t_min   0.993
_shelx_estimated_absorpt_t_max   0.999
_shelxl_version_number           2014/6
_shelx_res_checksum              10597