Electricity mediated [3+2]-cycloaddition of N-sulfonylcyclopropanes with olefins via N-centered radical intermediates: access to cyclopentane analogs
Saha, Debarshi; Taily, Irshad Maajid; Banerjee, Nakshatra; Banerjee, Prabal; Chemical Communications  (2022) –; doi:10.1039/D2CC00761D

data_7129914
_publ_section_title
;
 Electricity mediated [3+2]-cycloaddition of N-sulfonylcyclopropanes with
 olefins via N-centered radical intermediates: access to cyclopentane
 analogs
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC00761D
_journal_year                    2022
_chemical_formula_moiety         'C21 H25 N O4 S'
_chemical_formula_sum            'C21 H25 N O4 S'
_chemical_formula_weight         387.48
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-01-30 deposited with the CCDC.	2022-03-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.732(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.4139(12)
_cell_length_b                   8.4945(6)
_cell_length_c                   17.2042(15)
_cell_measurement_reflns_used    28113
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.7
_cell_measurement_theta_min      2.6
_cell_volume                     2077.6(3)
_computing_cell_refinement       'APEX2 (Bruker, 2014); SAINT (Bruker, 2014)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014);XPREP(Sheldrick,2014)'
_computing_molecular_graphics    'Ortep, Platon, mercury'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 10.233
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            28113
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.733
_diffrn_reflns_theta_min         2.567
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6519
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_meas      1.23
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.280
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3962
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0503
_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^)+(0.0557P)^2^+0.9282P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1393
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2816
_reflns_number_total             3962
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00761d2.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7129914
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.946
_shelx_estimated_absorpt_t_max   0.951
_shelx_res_checksum              95614