Electrochemical oxidative cyclization of activated alkynes with diselenides or disulfides: access to functionalized coumarins or quinolinones
Hua, Jiawei; Fang, Zheng; Xu, Jia; Bian, Mixue; Liu, ChengKou; He, Wei; Zhu, Ning; Yang, Zhao; Guo, Kai; Green Chemistry 21 (2019) 4706–; doi:10.1039/C9GC02131K

data_7233311
_publ_section_title
;
 Electrochemical oxidative cyclization of activated alkynes with
 diselenides or disulfides: access to functionalized coumarins or
 quinolinones
;
_journal_issue                   17
_journal_name_full               'Green Chemistry'
_journal_page_first              4706
_journal_paper_doi               10.1039/C9GC02131K
_journal_volume                  21
_journal_year                    2019
_chemical_formula_sum            'C23 H16 O3 Se'
_chemical_formula_weight         419.32
_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_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-06-22 deposited with the CCDC.    2019-08-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.315(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9403(7)
_cell_length_b                   17.1323(14)
_cell_length_c                   14.1867(12)
_cell_measurement_reflns_used    9988
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      53.89
_cell_measurement_theta_min      3.58
_cell_volume                     1878.0(3)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13163
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         53.894
_diffrn_reflns_theta_min         3.577
_exptl_absorpt_coefficient_mu    1.890
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.596
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3414
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.173
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0383
_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^)+(0.0321P)^2^+1.8319P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1020
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3226
_reflns_number_total             3414
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9gc02131k2.cif
_cod_data_source_block           20190529ZNZ4736_0m_a
_cod_depositor_comments          'Adding full bibliography for 7233311.cif.'
_cod_database_code               7233311
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.727
_shelx_estimated_absorpt_t_max   0.819
_shelx_res_checksum              16827