Direct (het)arylation of tetrahydroisoquinolines via a metal and oxidant free C(sp<sup>3</sup>)-H functionalization enabled three component reaction.
Haldar, Surajit; Jana, Chandan K.; Organic & biomolecular chemistry 17 (2019) 1800–1804; doi:10.1039/c8ob02309c

data_7156590
_publ_section_title
;
 Direct (het)arylation of tetrahydroisoquinolines via a metal and oxidant
 free C(sp<sup>3</sup>)-H functionalization enabled three component
 reaction.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1800
_journal_page_last               1804
_journal_paper_doi               10.1039/c8ob02309c
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C29 H23 N O3'
_chemical_formula_sum            'C29 H23 N O3'
_chemical_formula_weight         433.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-09-18 deposited with the CCDC.
2018-11-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.480(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.1652(8)
_cell_length_b                   15.1364(13)
_cell_length_c                   19.9955(13)
_cell_measurement_reflns_used    2291
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.2980
_cell_measurement_theta_min      3.3740
_cell_volume                     4401.3(5)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1058
_diffrn_reflns_av_unetI/netI     0.1436
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16211
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.998
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       block
_exptl_crystal_F_000             1824.0
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate and Hexane'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   0.980
_exptl_transmission_factor_min   0.973
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.629
_refine_diff_density_rms         0.150
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.192
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     597
_refine_ls_number_reflns         7645
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.192
_refine_ls_R_factor_all          0.1957
_refine_ls_R_factor_gt           0.0905
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+5.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1964
_refine_ls_wR_factor_ref         0.3323
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3089
_reflns_number_total             7645
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02309c2.cif
_cod_data_source_block           CKJ-SH-03-148P
_cod_depositor_comments          'Adding full bibliography for 7156590.cif.'
_cod_database_code               7156590
_shelx_shelxl_version_number     2014/7
_exptl_absorpt_special_details   SADABS
_shelx_res_checksum              1290
_shelx_hkl_checksum              31095