Dual Gold/Photoredox-Catalyzed Bis-Arylative Cyclization of Chiral Homopropargyl Sulfonamides with Diazonium Salts: Rapid Access to Enantioenriched 2,3-Dihydropyrroles
Wang, Ze-Shu; Tan, Tong-De; Wang, Cai-Ming; Yuan, Ding-Qiang; Zhang, Te; zhu, pengfei; Zhu, Chunyin; Zhou, Jin-Mei; Ye, Long-Wu; Chem. Commun.  (2017) –; doi:10.1039/C7CC03262E

data_7120187
_publ_section_title
;
 Dual Gold/Photoredox-Catalyzed Bis-Arylative Cyclization of Chiral
 Homopropargyl Sulfonamides with Diazonium Salts: Rapid Access to
 Enantioenriched 2,3-Dihydropyrroles
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC03262E
_journal_year                    2017
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C29 H23 F2 N O2 S'
_chemical_formula_sum            'C29 H23 F2 N O2 S'
_chemical_formula_weight         487.54
_chemical_name_systematic
(R)-4,5-bis(4-fluorophenyl)-2-phenyl-1-tosyl-2,3-dihydro-1H-pyrrole
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-04-02
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2017-04-04 deposited with the CCDC.
2017-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.780(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.287(2)
_cell_length_b                   10.555(2)
_cell_length_c                   12.485(3)
_cell_measurement_reflns_used    7302
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      28.47
_cell_measurement_theta_min      2.20
_cell_volume                     1217.6(5)
_computing_cell_refinement       'SAINT v6.28A (Bruker, 2002)'
_computing_data_reduction        'SAINT v6.28A (Bruker, 2002)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10225
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.644
_diffrn_reflns_theta_min         2.204
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.759814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS v.2.03 (Bruker,200?) was used for absorption correction.
R(int) was 0.1408 before and 0.0551 after correction.
The Ratio of minimum to maximum transmission is 0.7598.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane and ethyl acetate'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.05(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         5443
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0461
_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^)+(0.0642P)^2^+0.0798P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1172
_reflns_Friedel_coverage         0.903
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.925
_reflns_number_gt                5329
_reflns_number_total             5443
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc03262e2.cif
_cod_data_source_block           y0330m_pl
_cod_database_code               7120187
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.95(9)
 0.05(9)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
3.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C21(H21), C10(H10), C29(H29), C18(H18), C12(H12), C7(H7), C19(H19),
 C22(H22), C6(H6), C20(H20), C9(H9), C15(H15), C13(H13), C28(H28), C25(H25),
 C24(H24)
3.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_olex2_submission_special_instructions 'No special instructions were received'