L-Proline-catalyzed regioselective C1 arylation of tetrahydroisoquinolines through a multicomponent reaction under solvent-free conditions.
Rahman, Iftakur; Deka, Bhaskar; Thakuria, Ranjit; Deb, Mohit L.; Baruah, Pranjal K.; Organic & biomolecular chemistry 18 (2020) 6514–6518; doi:10.1039/d0ob01363c

data_7157669
_publ_section_title
;
 L-Proline-catalyzed regioselective C1 arylation of
 tetrahydroisoquinolines through a multicomponent reaction under
 solvent-free conditions.
;
_journal_issue                   33
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6514
_journal_page_last               6518
_journal_paper_doi               10.1039/d0ob01363c
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C20 H18 N6'
_chemical_formula_sum            'C20 H18 N6'
_chemical_formula_weight         342.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2020-05-17 deposited with the CCDC.	2020-08-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.8660(5)
_cell_length_b                   8.1481(8)
_cell_length_c                   18.3926(18)
_cell_measurement_reflns_used    1530
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.67
_cell_measurement_theta_min      2.73
_cell_volume                     879.11(14)
_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-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.654
_diffrn_measured_fraction_theta_max 0.719
_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  0.0404
_diffrn_reflns_av_unetI/netI     0.0728
_diffrn_reflns_Laue_measured_fraction_full 0.654
_diffrn_reflns_Laue_measured_fraction_max 0.719
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3323
_diffrn_reflns_point_group_measured_fraction_full 0.654
_diffrn_reflns_point_group_measured_fraction_max 0.719
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.163
_diffrn_reflns_theta_min         2.215
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_transmission_factor_max   0.989
_exptl_transmission_factor_min   0.985
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.168
_refine_ls_extinction_coef       0.38(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1548
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.973
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0588
_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^)+(0.0792P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1246
_refine_ls_wR_factor_ref         0.1628
_reflns_Friedel_coverage         0.000
_reflns_number_gt                937
_reflns_number_total             1548
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01363c2.cif
_cod_data_source_block           ir_35m
_cod_depositor_comments
'Adding full bibliography for 7157669--7157670.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7157669
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.986
_shelx_estimated_absorpt_t_max   0.990
_exptl_absorpt_special_details   'Sheldrick,G.M.,2015,University of gottingen'
_shelx_res_checksum              45792
_shelx_hkl_checksum              97637