Copper-catalyzed radical Heck type cyclization: a three-component reaction of DABCO·(SO2)2, aryldiazonium tetrafluoroborates and dienes toward sulfonated benzo- seven-membered nitrogen heterocycles
Wang, Hepan; Wang, Bingbing; Sun, Song; Cheng, Jiang; Organic Chemistry Frontiers 5 (2018) 2547–; doi:10.1039/C8QO00615F

data_1554371
_publ_section_title
;
 Copper-catalyzed radical Heck type cyclization: a three-component
 reaction of DABCO&#x00B7;(SO2)2, aryldiazonium tetrafluoroborates and
 dienes toward sulfonated benzo- seven-membered nitrogen heterocycles
;
_journal_issue                   17
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2547
_journal_paper_doi               10.1039/C8QO00615F
_journal_volume                  5
_journal_year                    2018
_chemical_formula_sum            'C25 H22 Cl N O3 S'
_chemical_formula_weight         451.94
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2018-04-10 deposited with the CCDC.
2018-07-18 downloaded from the CCDC.
;
_cell_angle_alpha                69.168(2)
_cell_angle_beta                 73.012(2)
_cell_angle_gamma                86.849(2)
_cell_formula_units_Z            2
_cell_length_a                   10.2719(7)
_cell_length_b                   10.4262(7)
_cell_length_c                   11.7012(8)
_cell_measurement_reflns_used    5562
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.30
_cell_volume                     1118.45(13)
_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-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0412
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7679
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.008
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_min         2.093
_exptl_absorpt_coefficient_mu    0.291
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.615
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3909
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0596P)^2^+0.4843P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1153
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3423
_reflns_number_total             3909
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00615f2.cif
_cod_data_source_block           20180409_0m_a
_cod_database_code               1554371
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.939
_shelx_estimated_absorpt_t_max   0.949
_shelx_res_checksum              6802
_shelx_hkl_checksum              51280