Organocatalytic Electrosynthesis of Cinnolines through Cascade Radical Cyclization and Migration
Cai, Chen; Lu, Yi; Yuan, Chengcheng; Fang, Zheng; Yang, Xiaobing; Liu, Chengkou; Guo, Kai; ACS Sustainable Chemistry & Engineering 9 (2021) 16989–16996; doi:10.1021/acssuschemeng.1c05810

data_4519267
_publ_section_title
;
 Organocatalytic Electrosynthesis of Cinnolines through Cascade Radical
 Cyclization and Migration
;
_journal_issue                   50
_journal_name_full               'ACS Sustainable Chemistry &amp; Engineering'
_journal_page_first              16989
_journal_page_last               16996
_journal_paper_doi               10.1021/acssuschemeng.1c05810
_journal_volume                  9
_journal_year                    2021
_chemical_formula_sum            'C22 H15 Cl N2 O'
_chemical_formula_weight         358.81
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 125.086(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   31.3976(9)
_cell_length_b                   6.9692(2)
_cell_length_c                   19.2078(5)
_cell_measurement_reflns_used    3343
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      73.1960
_cell_measurement_theta_min      3.4300
_cell_volume                     3439.25(19)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0826
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15974
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.391
_diffrn_reflns_theta_min         3.440
_exptl_absorpt_coefficient_mu    2.065
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79335
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_description       'yellow solid'
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.518
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3424
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0543
_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^)+(0.1000P)^2^+1.9000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1459
_refine_ls_wR_factor_ref         0.1602
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2757
_reflns_number_total             3424
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sc1c05810_si_002.cif
_cod_data_source_block           X
_cod_original_cell_volume        3439.25(18)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4519267
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.683
_shelx_estimated_absorpt_t_max   0.820
_shelx_res_checksum              41881
_shelx_hkl_checksum              80702