External oxidant-free oxidation/[3+2] cycloaddition/ aromatization cascade: electrochemical synthesis of polycyclic N-heterocycles
Qiang, Wang; Yuan, Ting; Liu, Qiang; Xu, Yong; Xie, Guanqun; Lv, Xin; Ding, Shujiang; Li, Chen; Wang, Xiaoxia; Chemical Communications  (2019) –; doi:10.1039/C9CC04336E

data_7123693
_publ_section_title
;
 External oxidant-free oxidation/[3+2] cycloaddition/ aromatization
 cascade: electrochemical synthesis of polycyclic N-heterocycles
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC04336E
_journal_year                    2019
_chemical_formula_sum            'C22 H18 Cl N O3'
_chemical_formula_weight         379.82
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc229zky
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-05-15 deposited with the CCDC.    2019-06-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.623(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7422(7)
_cell_length_b                   8.7533(5)
_cell_length_c                   21.6004(14)
_cell_measurement_reflns_used    7898
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.51
_cell_volume                     1829.7(2)
_computing_cell_refinement       'Siemens SMART & SAINT'
_computing_data_collection       'Siemens SMART'
_computing_data_reduction        'Siemens XPREP'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'S'Siemens SHELXTL'
_computing_structure_solution    'Siemens SHELXTL'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_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  0.0284
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            13175
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.519
_diffrn_reflns_theta_min         2.513
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  .0000
_exptl_absorpt_correction_T_min  .0000
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          .32
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .12
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4168
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_gt           0.0431
_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^)+(0.0641P)^2^+0.6389P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1281
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3694
_reflns_number_total             4168
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc04336e2.cif
_cod_data_source_block           a
_cod_database_code               7123693
_shelx_shelxl_version_number     2014/7
_refine_ls_r_factor_ref          0.0474
_shelx_res_checksum              99503
_shelx_hkl_checksum              62824