Palladium-catalyzed domino Heck/intermolecular cross-coupling: efficient synthesis of 4-alkylated isoquinoline derivatives.
Yao, Tuanli; Liu, Tao; Zhang, Changhui; Chemical communications (Cambridge, England) 53 (2017) 2386–2389; doi:10.1039/c6cc10075a

data_7119581
_publ_section_title
;
 Palladium-catalyzed domino Heck/intermolecular cross-coupling: efficient
 synthesis of 4-alkylated isoquinoline derivatives.
;
_journal_issue                   15
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2386
_journal_page_last               2389
_journal_paper_doi               10.1039/c6cc10075a
_journal_volume                  53
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_sum            'C25 H21 N O'
_chemical_formula_weight         351.43
_chemical_name_systematic
4-((3-Methyl-2,3-dihydrobenzofuran-3-yl)methyl)-3-phenylisoquinoline
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2016-12-18 deposited with the CCDC.
2017-02-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.0748(19)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.1675(4)
_cell_length_b                   13.1365(8)
_cell_length_c                   10.0074(6)
_cell_measurement_reflns_used    4014
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.72
_cell_measurement_theta_min      3.101
_cell_volume                     924.71(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_av_unetI/netI     0.0760
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14464
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.604
_diffrn_reflns_theta_min         3.101
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.207
_exptl_crystal_size_min          0.113
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 922 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.9(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4285
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.1326
_refine_ls_R_factor_gt           0.0618
_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^)+(0.0600P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1316
_reflns_Friedel_coverage         0.914
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                2516
_reflns_number_total             4285
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc10075a2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7119581.cif.'
_cod_database_code               7119581
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.991
_shelxl_version_number           2013-4
_shelx_res_checksum              21603