Regioselective synthesis of 3,4-disubstituted isocoumarins through the Pd-catalyzed annulation of 2-iodoaromatic acids with ynamides
Hongxu Liu; Yanyan Yang; Jie Wu; Xiao-Na Wang; Junbiao Chang; Chem.Commun. 52 (2016) 6801–; doi:

data_7119128
_publ_section_title
;
 Regioselective synthesis of 3,4-disubstituted isocoumarins through the
 Pd-catalyzed annulation of 2-iodoaromatic acids with ynamides
;
_journal_name_full               Chem.Commun.
_journal_page_first              6801
_journal_volume                  52
_journal_year                    2016
_chemical_formula_sum            'C24 H21 N O4 S'
_chemical_formula_weight         419.48
_chemical_name_systematic
N-benzyl-4-methyl-N-(4-methyl-1-oxo-1H-isochromen-3-yl)benzenesulfonamide
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-02-20 deposited with the CCDC.
2016-04-18 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 102.6900(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.2840(3)
_cell_length_b                   26.1213(7)
_cell_length_c                   15.8601(4)
_cell_measurement_reflns_used    9996
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      68.5518
_cell_measurement_theta_min      3.3198
_cell_volume                     4156.4(2)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      170(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            29434
_diffrn_reflns_theta_full        68.55
_diffrn_reflns_theta_max         68.55
_diffrn_reflns_theta_min         3.32
_diffrn_standards_number         29434
_exptl_absorpt_coefficient_mu    1.642
_exptl_absorpt_correction_T_max  0.9753
_exptl_absorpt_correction_T_min  0.9624
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS(Bruker 2000)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1760
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane/ethyl acetate'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     545
_refine_ls_number_reflns         7605
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0485P)^2^+1.4505P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0924
_reflns_number_gt                6658
_reflns_number_total             7605
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc01565d2.cif
_cod_data_source_block           a-auto
_cod_database_code               7119128