A facile one-pot synthesis of N-acyl-1-cyano-1,2,3,4-tetrahydroisoquinoline via a photoredox and Reissert-type reaction from 1,2,3,4-tetrahydroisoquinolines
Yuan, Zi-Yi; Zhang, Zheng-Qian; Liang, Jun-Rong; Lin, Chu-Yan; Peng, Dan-Li; Cui, Bao-Dong; Mou, Xue-Qing; Zhang, Yun; Chen, Yong-Zheng; New Journal of Chemistry 47 (2023) 15847–15851; doi:10.1039/D3NJ02600K

data_7062630
_publ_section_title
;
 A facile one-pot synthesis of
 N-acyl-1-cyano-1,2,3,4-tetrahydroisoquinoline via a photoredox and
 Reissert-type reaction from 1,2,3,4-tetrahydroisoquinolines
;
_journal_issue                   34
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              15847
_journal_page_last               15851
_journal_paper_doi               10.1039/D3NJ02600K
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C12 H12 N2 O'
_chemical_formula_sum            'C12 H12 N2 O'
_chemical_formula_weight         200.24
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-02-21
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-05-17 deposited with the CCDC.	2023-08-01 downloaded from the CCDC.
;
_cell_angle_alpha                102.299(15)
_cell_angle_beta                 97.775(15)
_cell_angle_gamma                99.273(14)
_cell_formula_units_Z            2
_cell_length_a                   7.1562(12)
_cell_length_b                   8.1948(14)
_cell_length_c                   9.4259(17)
_cell_measurement_reflns_used    1166
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      26.7510
_cell_measurement_theta_min      2.9030
_cell_volume                     524.71(17)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -77.00  18.00   1.00    1.99    --  -11.27 -77.00-150.00   95
  2  \w    -54.00  35.00   1.00    1.99    --   11.90 -57.00 -30.00   89
  3  \w    -16.00  84.00   1.00    1.99    --   11.90  57.00 120.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0267095000
_diffrn_orient_matrix_UB_12      0.0528986000
_diffrn_orient_matrix_UB_13      0.0724910000
_diffrn_orient_matrix_UB_21      0.0549462000
_diffrn_orient_matrix_UB_22      0.0629253000
_diffrn_orient_matrix_UB_23      -0.0270227000
_diffrn_orient_matrix_UB_31      -0.0817050000
_diffrn_orient_matrix_UB_32      0.0374738000
_diffrn_orient_matrix_UB_33      -0.0116588000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0899
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3302
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.246
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.01029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_description       block
_exptl_crystal_F_000             212
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.115(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1845
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.965
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0566
_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^)+(0.0599P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1435
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1239
_reflns_number_total             1845
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj02600k2.cif
_cod_data_source_block           c1
_cod_depositor_comments
'Adding full bibliography for 7062629--7062630.cif.'
_cod_original_cell_volume        524.71(16)
_cod_database_code               7062630
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.989
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_shelx_res_checksum              5186
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 20.718
_oxdiff_exptl_absorpt_empirical_full_min 0.357