Regioselective Synthesis of Benzo-fused Tetrahydroisoquinoline-based Biaryls through a Tandem One-pot Halogenation of p-Benzynes from Enediynes and Suzuki-Miyaura Coupling.
Das, Eshani; Basak, Amit; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02874

data_4037787
_publ_section_title
;
 Regioselective Synthesis of Benzo-fused Tetrahydroisoquinoline-based
 Biaryls through a Tandem One-pot Halogenation of p-Benzynes from
 Enediynes and Suzuki-Miyaura Coupling.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02874
_journal_year                    2019
_chemical_formula_sum            'C28 H24 F3 N O3 S'
_chemical_formula_weight         511.54
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   12.383(2)
_cell_length_b                   12.964(3)
_cell_length_c                   56.938(11)
_cell_measurement_reflns_used    3138
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.363
_cell_measurement_theta_min      0.715
_cell_volume                     9140(3)
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45 ( Bruker, 2003)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    SIR-97
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2171
_diffrn_reflns_av_unetI/netI     0.1221
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       62
_diffrn_reflns_limit_l_min       -63
_diffrn_reflns_number            65544
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        23.363
_diffrn_reflns_theta_max         23.363
_diffrn_reflns_theta_min         0.715
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  0.931
_exptl_absorpt_correction_T_min  0.857
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             4256
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       0.0041(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     650
_refine_ls_number_reflns         6575
_refine_ls_number_restraints     432
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.2018
_refine_ls_R_factor_gt           0.1029
_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^)+27.1854P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2018
_refine_ls_wR_factor_ref         0.2505
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3318
_reflns_number_total             6575
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02874_si_002.cif
_cod_data_source_block           Eshani
_cod_database_code               4037787
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              73561
_shelx_hkl_checksum              9091