Modular synthesis of 3-substituted isocoumarins <i>via</i> silver-catalyzed aerobic oxidation/<i>6-endo</i> heterocyclization of <i>ortho</i>-alkynylbenzaldehydes.
Wu, Hao; Wang, Yi-Chun; Shatskiy, Andrey; Li, Qiu-Yan; Liu, Jian-Quan; Kärkäs, Markus D; Wang, Xiang-Shan; Organic & biomolecular chemistry 19 (2021) 6657–6664; doi:10.1039/d1ob01065d

data_7158167
_publ_section_title
;
 Modular synthesis of 3-substituted isocoumarins <i>via</i>
 silver-catalyzed aerobic oxidation/<i>6-endo</i> heterocyclization of
 <i>ortho</i>-alkynylbenzaldehydes.
;
_journal_issue                   30
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6657
_journal_page_last               6664
_journal_paper_doi               10.1039/d1ob01065d
_journal_volume                  19
_journal_year                    2021
_chemical_formula_sum            'C16 H12 O3'
_chemical_formula_weight         252.26
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc26x0x2
_audit_creation_method           SHELXL-97
_audit_update_record
;
2020-12-28 deposited with the CCDC.	2021-07-09 downloaded from the CCDC.
;
_cell_angle_alpha                76.201(3)
_cell_angle_beta                 81.124(3)
_cell_angle_gamma                73.395(3)
_cell_formula_units_Z            2
_cell_length_a                   7.0451(17)
_cell_length_b                   7.3918(17)
_cell_length_c                   12.782(3)
_cell_measurement_temperature    296(2)
_cell_volume                     616.8(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0195
_diffrn_reflns_av_sigmaI/netI    0.0167
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6292
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.94
_exptl_absorpt_coefficient_mu    0.094
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             264
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.30(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2159
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0454
_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^)+(0.0703P)^2^+0.1220P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1317
_reflns_number_gt                1918
_reflns_number_total             2159
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1ob01065d2.cif
_cod_data_source_block           a
_cod_depositor_comments          'Adding full bibliography for 7158167.cif.'
_cod_database_code               7158167