Nickel(II)-catalyzed asymmetric thio-Claisen rearrangement of α-diazo pyrazoleamides with thioindoles.
Yang, Wei; Lin, Xiaobin; Zhang, Yongyan; Cao, Weidi; Liu, Xiaohua; Feng, Xiaoming; Chemical communications (Cambridge, England) 56 (2020) 10002–10005; doi:10.1039/d0cc04590j

data_7126954
_publ_section_title
;
 Nickel(II)-catalyzed asymmetric thio-Claisen rearrangement of \a-diazo
 pyrazoleamides with thioindoles.
;
_journal_issue                   69
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10002
_journal_page_last               10005
_journal_paper_doi               10.1039/d0cc04590j
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H27 N3 O2 S'
_chemical_formula_sum            'C26 H27 N3 O2 S'
_chemical_formula_weight         445.56
_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
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-04-21 deposited with the CCDC.	2020-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.6860(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.7950(4)
_cell_length_b                   7.6360(2)
_cell_length_c                   13.0428(4)
_cell_measurement_reflns_used    9794
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      74.41
_cell_measurement_theta_min      3.73
_cell_volume                     1157.86(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Photon II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            42444
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.403
_diffrn_reflns_theta_min         3.730
_exptl_absorpt_coefficient_mu    1.460
_exptl_absorpt_correction_T_max  0.9155
_exptl_absorpt_correction_T_min  0.7412
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       fragment
_exptl_crystal_F_000             472
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: THF, Ether, Hexane'
_exptl_crystal_size_max          0.231
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.092
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
; 
 Flack x determined using 2067 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.038(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4691
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0260
_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^)+(0.0384P)^2^+0.1865P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0687
_refine_ls_wR_factor_ref         0.0693
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                4605
_reflns_number_total             4691
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc04590j2.cif
_cod_data_source_block           yaw003
_cod_depositor_comments
'Adding full bibliography for 7126952--7126954.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7126954
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.729
_shelx_estimated_absorpt_t_max   0.877
_shelx_res_checksum              50352
_shelx_hkl_checksum              83285