Stereoselective Copper-Catalyzed Cross-Coupling of Aziridines with Benzimidazoles via Nucleophilic Ring Opening and C(sp(2))-H Functionalization.
De, Pinaki Bhusan; Pradhan, Sourav; Punniyamurthy, Tharmalingam; The Journal of organic chemistry 82 (2017) 3183–3191; doi:10.1021/acs.joc.7b00265

data_4032341
_publ_section_title
;
 Stereoselective Copper-Catalyzed Cross-Coupling of Aziridines with
 Benzimidazoles via Nucleophilic Ring Opening and C(sp(2))-H
 Functionalization.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3183
_journal_page_last               3191
_journal_paper_doi               10.1021/acs.joc.7b00265
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C22 H18 Cl N3 O2 S'
_chemical_formula_sum            'C22 H18 Cl N3 O2 S'
_chemical_formula_weight         423.90
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 100.212(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7527(6)
_cell_length_b                   8.3311(6)
_cell_length_c                   24.3083(18)
_cell_measurement_reflns_used    2657
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.7650
_cell_measurement_theta_min      3.5290
_cell_volume                     1943.8(2)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD and area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7823
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_min         2.980
_exptl_absorpt_coefficient_mu    0.329
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_description       needle
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   0.942
_exptl_transmission_factor_min   0.910
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3518
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0496
_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^)+(0.0100P)^2^+5.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1380
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2667
_reflns_number_total             3518
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00265_si_001.cif
_cod_data_source_block           pbd-4-cl-crys
_cod_depositor_comments
'Adding full bibliography for 4032341--4032342.cif.'
_cod_database_code               4032341
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              42632
_shelx_hkl_checksum              5619