Silver-Mediated Radical Cyclization of Alkynoates and α-Keto Acids Leading to Coumarins via Cascade Double C-C Bond Formation.
Yan, Kelu; Yang, Daoshan; Wei, Wei; Wang, Fen; Shuai, Yuanyuan; Li, Qiannan; Wang, Hua; The Journal of organic chemistry 80 (2015) 1550–1556; doi:10.1021/jo502474z

data_4030453
_publ_section_title
;
 Silver-Mediated Radical Cyclization of Alkynoates and \a-Keto Acids
 Leading to Coumarins via Cascade Double C-C Bond Formation.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1550
_journal_page_last               1556
_journal_paper_doi               10.1021/jo502474z
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C22 H14 O3'
_chemical_formula_sum            'C22 H14 O3'
_chemical_formula_weight         326.33
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-10-28 deposited with the CCDC.
2014-12-26 downloaded from the CCDC.
;
_cell_angle_alpha                61.424(2)
_cell_angle_beta                 78.793(2)
_cell_angle_gamma                65.588(2)
_cell_formula_units_Z            2
_cell_length_a                   9.696(2)
_cell_length_b                   10.159(2)
_cell_length_c                   10.316(2)
_cell_measurement_reflns_used    2371
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.63
_cell_measurement_theta_min      2.31
_cell_volume                     812.6(3)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker SMART APEX detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6335
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9843
_exptl_absorpt_correction_T_min  0.9740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.047
_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     226
_refine_ls_number_reflns         3137
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0590P)^2^+0.0800P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1154
_reflns_number_gt                2484
_reflns_number_total             3137
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502474z_si_002.cif
_cod_data_source_block           sad
_cod_depositor_comments          'Adding full bibliography for 4030453.cif.'
_cod_original_cell_volume        812.5(3)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4030453