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_7119129
_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            'C30 H25 N O4 S'
_chemical_formula_weight         495.57
_chemical_name_systematic
N-benzyl-4-methyl-N-(1-oxo-4-(p-tolyl)-1H-isochromen-3-yl)benzenesulfonamide
_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
;
2016-02-20 deposited with the CCDC.
2016-04-18 downloaded from the CCDC.
;
_cell_angle_alpha                71.7040(10)
_cell_angle_beta                 82.1800(10)
_cell_angle_gamma                66.1200(10)
_cell_formula_units_Z            4
_cell_length_a                   12.2963(4)
_cell_length_b                   13.8393(4)
_cell_length_c                   16.8203(4)
_cell_measurement_reflns_used    9971
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      24.14
_cell_measurement_theta_min      2.38
_cell_volume                     2484.87(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        "'Bruker SAINT"
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            61154
_diffrn_reflns_theta_full        25.44
_diffrn_reflns_theta_max         25.44
_diffrn_reflns_theta_min         1.28
_exptl_absorpt_coefficient_mu    0.168
_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            colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane/ethyl acetate'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.624
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.160
_refine_ls_extinction_coef       0.049(3)
_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   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     650
_refine_ls_number_reflns         9162
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0550
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0956P)^2^+0.4412P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1665
_reflns_number_gt                6646
_reflns_number_total             9162
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc01565d2.cif
_cod_data_source_block           a
_cod_original_cell_volume        2484.87(12)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7119129