Cationic Co(I) Catalysts for Regiodivergent Hydroalkenylation of 1,6-Enynes: An Uncommon cis-β-C‒H Activation Leads to Z-Selective Coupling of Acrylates
Herbort, James H.; Lalisse, Remy F.; Hadad, Christopher M.; RajanBabu, T. V.; ACS Catalysis  (2021) 9605–9617; doi:10.1021/acscatal.1c02530

data_4518900
_publ_section_title
;
 Cationic Co(I) Catalysts for Regiodivergent Hydroalkenylation of
 1,6-Enynes: An Uncommon cis-\b-C--H Activation Leads to Z-Selective
 Coupling of Acrylates
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              9605
_journal_page_last               9617
_journal_paper_doi               10.1021/acscatal.1c02530
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21  H23  N1  O2  S1'
_chemical_formula_sum            'C21 H23 N O2 S'
_chemical_formula_weight         353.46
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      9
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2019-07-30T16:11:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90.194(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.1894(6)
_cell_length_b                   15.9729(6)
_cell_length_c                   15.9472(5)
_cell_measurement_reflns_used    9969
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      27.875
_cell_measurement_theta_min      2.853
_cell_measurement_wavelength     0.71073
_cell_volume                     3869.1(2)
_computing_cell_refinement       'SAINT v8.38A (Bruker, 2017)'
_computing_data_collection       'Apex3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2017)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT_2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      220(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON II CPAD'
_diffrn_radiation_monochromator  'TRIUMPH curved--crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            74424
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.898
_diffrn_reflns_theta_min         2.852
_diffrn_source                   'fine--focus tube'
_exptl_absorpt_coefficient_mu    0.18
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS )'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 4116 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.016(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     455
_refine_ls_number_reflns         9224
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.031
_refine_ls_R_factor_gt           0.0281
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0528P)^2^+0.3816P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0821
_reflns_number_gt                8706
_reflns_number_total             9224
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c02530_si_002.cif
_cod_data_source_block           RajanBabu2252a
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               4518900