Visible-Light-Mediated Annulation of Electron-Rich Alkenes and Nitrogen-Centered Radicals from N-Sulfonylallylamines: Construction of Chloromethylated Pyrrolidine Derivatives.
Crespin, Lorène N S; Greb, Andreas; Blakemore, David C.; Ley, Steven V.; The Journal of organic chemistry 82 (2017) 13093–13108; doi:10.1021/acs.joc.7b02146

data_4033194
_publ_section_title
;
 Visible-Light-Mediated Annulation of Electron-Rich Alkenes and
 Nitrogen-Centered Radicals from N-Sulfonylallylamines: Construction of
 Chloromethylated Pyrrolidine Derivatives.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13093
_journal_page_last               13108
_journal_paper_doi               10.1021/acs.joc.7b02146
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H24 Cl N O3 S'
_chemical_formula_sum            'C20 H24 Cl N O3 S'
_chemical_formula_weight         393.91
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.1684(3)
_cell_length_b                   9.6090(2)
_cell_length_c                   14.3695(3)
_cell_measurement_reflns_used    7972
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      66.68
_cell_measurement_theta_min      4.60
_cell_volume                     1956.32(7)
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-100'
_diffrn_measurement_method       '\w and \f-scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9433
_diffrn_reflns_point_group_measured_fraction_full 0.917
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_theta_full        66.678
_diffrn_reflns_theta_max         66.678
_diffrn_reflns_theta_min         4.602
_diffrn_source                   'Incoatec I\mS Cu microsource'
_exptl_absorpt_coefficient_mu    2.885
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6674
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
Flack x determined using 1245 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.039(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3190
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0259
_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^)+(0.0312P)^2^+0.1448P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0632
_refine_ls_wR_factor_ref         0.0645
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    0.828
_reflns_Friedel_fraction_max     0.828
_reflns_number_gt                3043
_reflns_number_total             3190
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02146_si_001.cif
_cod_data_source_block           sl_b2_0016
_cod_depositor_comments
'Adding full bibliography for 4033193--4033194.cif.'
_cod_database_code               4033194
_cambridge_user_name             'Lorene Crespin'
_cambridge_user_crsid            lc667
_cambridge_supervisor_name       'Steven Ley'
_cambridge_supervisor_crsid      svl1000
_cambridge_crystallographer_name 'Andrew Bond'
_cambridge_crystallographer_crsid adb29
_cambridge_sample_id             lc565.2.2.2
_cambridge_data_id               SL_B2_0016
_ccdc_publ_extra_info
;
_cambridge_sample_id lc565.2.2.2
_cambridge_data_id SL_B2_0016
;
_shelx_estimated_absorpt_t_min   0.688
_shelx_estimated_absorpt_t_max   0.688
_shelx_res_checksum              27080
_shelx_hkl_checksum              91646