SmI2‑Mediated Intermolecular Addition-Elimination of Piperidine and Pyrrolidine N-α-Radicals with Arylacetylene Sulfones
Liu, Chang-Hong; Guo, Jiangming; Li, Xin; Sun, Jianting; Wei, Bangguo; Si, Chang-Mei; Chemical Communications  (2022) –; doi:10.1039/D2CC03984B

data_7130606
_publ_section_title
;
 SmI2&#x2011;Mediated Intermolecular Addition-Elimination of Piperidine
 and Pyrrolidine N-\a-Radicals with Arylacetylene Sulfones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC03984B
_journal_year                    2022
_chemical_formula_sum            'C23 H24 Br N O3'
_chemical_formula_weight         442.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2022-04-01 deposited with the CCDC.	2022-08-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.392(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.352(6)
_cell_length_b                   9.238(3)
_cell_length_c                   24.982(9)
_cell_measurement_reflns_used    3724
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      42.813
_cell_measurement_theta_min      4.918
_cell_volume                     4311(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_av_unetI/netI     0.0640
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            15624
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.464
_exptl_absorpt_coefficient_mu    1.929
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.825
_refine_diff_density_min         -0.593
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3782
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.1392
_refine_ls_R_factor_gt           0.0777
_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^)+(0.1272P)^2^+15.6619P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2233
_refine_ls_wR_factor_ref         0.2676
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2057
_reflns_number_total             3782
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc03984b2.cif
_cod_data_source_block           d8v22017
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7130606
_shelx_estimated_absorpt_t_min   0.699
_shelx_estimated_absorpt_t_max   0.801
_shelxl_version_number           2013-4
_shelx_res_checksum              71473
_shelx_hkl_checksum              37361