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_7129913
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-14
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_audit_update_record
;
2022-01-12 deposited with the CCDC.	2022-03-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.766(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.4901(9)
_cell_length_b                   9.8844(7)
_cell_length_c                   15.6641(11)
_cell_measurement_reflns_used    9817
_cell_measurement_temperature    298
_cell_measurement_theta_max      26.405
_cell_measurement_theta_min      2.305
_cell_volume                     2019.7(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            70148
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.413
_diffrn_reflns_theta_min         2.306
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5412
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1607 before and 0.0708 after correction.
The Ratio of minimum to maximum transmission is 0.7261.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       plank
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.356
_exptl_crystal_size_mid          0.227
_exptl_crystal_size_min          0.053
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4082
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0586P)^2^+0.4955P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1201
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3433
_reflns_number_total             4082
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00761d2.cif
_cod_data_source_block           pb_18_02_289_0m_a
_cod_database_code               7129913
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.937
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C11(H11A,H11B), C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C5(H5), C1(H1A), C2(H2), C20(H20), C16(H16), C19(H19),
 C18(H18), C17(H17)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C4(H4A,H4B,H4C)
;
_shelx_res_checksum              24490
_olex2_submission_special_instructions 'No special instructions were received'