Enantioselective zinc-mediated conjugate alkynylation of saccharin-derived 1-aza-butadienes.
Blay, Gonzalo; Castilla, Alvaro; Sanz, David; Sanz-Marco, Amparo; Vila, Carlos; Muñoz, M Carmen; Pedro, José R; Chemical communications (Cambridge, England) 56 (2020) 9461–9464; doi:10.1039/d0cc04221h

data_7126888
_publ_section_title
;
 Enantioselective zinc-mediated conjugate alkynylation of
 saccharin-derived 1-aza-butadienes.
;
_journal_issue                   66
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9461
_journal_page_last               9464
_journal_paper_doi               10.1039/d0cc04221h
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H16 Br N O2 S'
_chemical_formula_weight         414.31
_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   mixed
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2020-03-25 deposited with the CCDC.	2020-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.473(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.4286(4)
_cell_length_b                   7.2641(3)
_cell_length_c                   17.1612(8)
_cell_measurement_reflns_used    6139
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      27.4642
_cell_measurement_theta_min      2.7595
_cell_volume                     920.15(8)
_computing_cell_refinement       'APEX3, Bruker'
_computing_data_collection       'APEX3, Bruker'
_computing_data_reduction        'APEX3, Bruker'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    SHELXS-2014
_diffrn_ambient_temperature      250(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker S8 x-ray diffraction'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            31130
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.124
_diffrn_reflns_theta_min         2.760
_exptl_absorpt_coefficient_mu    2.360
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Empirical absorption correction'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.922
_refine_diff_density_min         -0.725
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1282 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.017(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         4915
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0451
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0710P)^2^+0.2898P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1343
_reflns_Friedel_coverage         0.857
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                3393
_reflns_number_total             4915
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc04221h2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7126888.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7126888
_shelx_estimated_absorpt_t_min   0.834
_shelx_estimated_absorpt_t_max   0.912
_shelxl_version_number           2014-1
_shelx_res_checksum              78411
_shelx_hkl_checksum              2316