L-Proline catalyzed multi-component synthesis of <i>N</i>-pyridyl-tetrahydroisoquinolines and their α-C(sp<sup>3</sup>)-H oxygenation.
Boruah, Aditi; Deb, Mohit L.; Thakuria, Ranjit; Baruah, Pranjal K.; Organic & biomolecular chemistry 22 (2024) 8608–8616; doi:10.1039/d4ob01343c

data_7160161
_publ_section_title
;
 L-Proline catalyzed multi-component synthesis of
 <i>N</i>-pyridyl-tetrahydroisoquinolines and their
 &#x3b1;-C(sp<sup>3</sup>)-H oxygenation.
;
_journal_issue                   43
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8608
_journal_page_last               8616
_journal_paper_doi               10.1039/d4ob01343c
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C22 H15 N5 O'
_chemical_formula_sum            'C22 H15 N5 O'
_chemical_formula_weight         365.39
_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   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2024-09-03 deposited with the CCDC.	2024-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 119.39(2)
_cell_angle_gamma                90
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_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.36
_cell_measurement_theta_min      2.80
_cell_volume                     2046.9(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
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_computing_molecular_graphics    'Bruker SHELXTL'
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_diffrn_ambient_temperature      293(2)
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_diffrn_measured_fraction_theta_max 0.907
_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  0.2157
_diffrn_reflns_av_unetI/netI     0.2430
_diffrn_reflns_Laue_measured_fraction_full 0.916
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            58088
_diffrn_reflns_point_group_measured_fraction_full 0.916
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.666
_diffrn_reflns_theta_min         1.956
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.090
_refine_diff_density_max         1.135
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       0.061(13)
_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   0.957
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4349
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.957
_refine_ls_R_factor_all          0.1723
_refine_ls_R_factor_gt           0.1019
_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^)+(0.1093P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2213
_refine_ls_wR_factor_ref         0.2767
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2063
_reflns_number_total             4349
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01343c2.cif
_cod_data_source_block           ab_21_i_0m
_cod_depositor_comments
'Adding full bibliography for 7160161--7160162.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7160161
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.988
_shelx_estimated_absorpt_t_max   0.993
_exptl_absorpt_special_details   'Sheldrick,G.M.,2015,University of gottingen'
_shelx_res_checksum              56029