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_7130605
_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_absolute_configuration ad
_chemical_formula_sum            'C12 H12 Br N O'
_chemical_formula_weight         266.14
_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
_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                 104.8590(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.1212(3)
_cell_length_b                   5.4427(2)
_cell_length_c                   11.9771(4)
_cell_measurement_reflns_used    3591
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      54.591
_cell_measurement_theta_min      6.457
_cell_volume                     574.71(3)
_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      213(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.988
_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  0.0263
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5679
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         3.244
_exptl_absorpt_coefficient_mu    3.549
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4234
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
; 
 Flack x determined using 799 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.027(8)
_refine_ls_extinction_coef       0.023(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         2216
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0246
_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^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0513
_refine_ls_wR_factor_ref         0.0536
_reflns_Friedel_coverage         0.784
_reflns_Friedel_fraction_full    0.971
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                2007
_reflns_number_total             2216
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc03984b2.cif
_cod_data_source_block           mo_d8v21878_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7130605
_shelx_estimated_absorpt_t_min   0.568
_shelx_estimated_absorpt_t_max   0.789
_shelxl_version_number           2013-4
_shelx_res_checksum              57053
_shelx_hkl_checksum              94526