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_4033193
_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 unk
_chemical_formula_moiety         'C25 H24 Cl N O2 S'
_chemical_formula_sum            'C25 H24 Cl N O2 S'
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_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
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_cell_angle_alpha                90
_cell_angle_beta                 90.3950(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.3211(2)
_cell_length_b                   8.5298(2)
_cell_length_c                   20.3965(8)
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_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1099.71(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL
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_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
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_diffrn_measured_fraction_theta_max 0.965
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_diffrn_measurement_method       '\w and \f-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       8
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_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9027
_diffrn_reflns_point_group_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.468
_diffrn_reflns_theta_min         3.804
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_T_max  0.937
_exptl_absorpt_correction_T_min  0.875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'
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_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.280
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_exptl_crystal_size_min          0.230
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
Flack x determined using 1547 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.14(4)
_refine_ls_extinction_coef       0.025(4)
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4530
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0391
_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^)+(0.0420P)^2^+0.1523P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0891
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_full    0.908
_reflns_Friedel_fraction_max     0.826
_reflns_number_gt                3979
_reflns_number_total             4530
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02146_si_002.cif
_cod_data_source_block           sl_k3_0012
_cod_depositor_comments
'Adding full bibliography for 4033193--4033194.cif.'
_cod_database_code               4033193
_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             LC639.1
_cambridge_data_id               SL_K3_0012
_ccdc_publ_extra_info
;
_cambridge_sample_id LC639.1
_cambridge_data_id SL_K3_0012
;
_shelx_estimated_absorpt_t_min   0.923
_shelx_estimated_absorpt_t_max   0.936
_shelx_res_checksum              9848
_shelx_hkl_checksum              81369