Diastereoselective dearomative bifunctionalization of isoquinolinium salts to access bridged tetrahydroisoquinolines
Pei, Jiaqi; Tang, Tiantian; Zhang, Jianing; Qin, Yunlong; Cheng, Pengfei; Wang, Qilin; New Journal of Chemistry 48 (2024) 16151–16154; doi:10.1039/D4NJ02968B

data_7063434
_publ_section_title
;
 Diastereoselective dearomative bifunctionalization of isoquinolinium
 salts to access bridged tetrahydroisoquinolines
;
_journal_issue                   37
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              16151
_journal_page_last               16154
_journal_paper_doi               10.1039/D4NJ02968B
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C41 H41 N2 O P'
_chemical_formula_sum            'C41 H41 N2 O P'
_chemical_formula_weight         608.73
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-04-16
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-06-13 deposited with the CCDC.	2024-09-02 downloaded from the CCDC.
;
_cell_angle_alpha                111.600(6)
_cell_angle_beta                 93.776(5)
_cell_angle_gamma                104.186(6)
_cell_formula_units_Z            2
_cell_length_a                   11.0596(7)
_cell_length_b                   11.2945(8)
_cell_length_c                   15.3318(9)
_cell_measurement_reflns_used    4385
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      73.1190
_cell_measurement_theta_min      3.1040
_cell_volume                     1700.3(2)
_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      air
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.956
_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    -26.00   1.00   1.00    1.00    --   41.11 -77.00   0.00   27
  2  \w      1.00  58.00   1.00    1.00    --   41.11 -99.00   0.00   57
  3  \w     66.00 109.00   1.00    1.00    --  106.95 -94.00 120.00   43
  4  \w     39.00 126.00   1.00    1.00    --  106.95 -45.00  60.00   87
  5  \w    111.00 178.00   1.00    1.00    --  106.95  30.00 120.00   67
  6  \w    122.00 169.00   1.00    1.00    --  106.95 125.00 -30.00   47
  7  \w    100.00 173.00   1.00    1.00    --  106.95 125.00  60.00   73
  8  \w     79.00 178.00   1.00    1.00    --  106.95  30.00-120.00   99
  9  \w     87.00 148.00   1.00    1.00    --  106.95  45.00-180.00   61
 10  \w     75.00 114.00   1.00    1.00    --  106.95  77.00  30.00   39
 11  \w     33.00  86.00   1.00    1.00    --  106.95 -30.00 -60.00   53
 12  \w     28.00  95.00   1.00    1.00    --  106.95 -94.00   0.00   67
 13  \w     36.00 119.00   1.00    1.00    --  106.95-125.00 -60.00   83
 14  \w     54.00  97.00   1.00    1.00    --   41.11-125.00-180.00   43
 15  \w     36.00 114.00   1.00    1.00    --  106.95-125.00 120.00   78
 16  \w    -48.00  -9.00   1.00    1.00    --  -41.11 125.00   0.00   39
 17  \w   -112.00 -13.00   1.00    1.00    --  -41.11 -57.00 120.00   99
 18  \w   -112.00 -17.00   1.00    1.00    --  -41.11 -38.00-150.00   95
;
_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      0.0244049000
_diffrn_orient_matrix_UB_12      -0.1236611000
_diffrn_orient_matrix_UB_13      -0.0742027000
_diffrn_orient_matrix_UB_21      0.1246810000
_diffrn_orient_matrix_UB_22      0.0264331000
_diffrn_orient_matrix_UB_23      0.0646313000
_diffrn_orient_matrix_UB_31      -0.0716860000
_diffrn_orient_matrix_UB_32      -0.0866563000
_diffrn_orient_matrix_UB_33      0.0485202000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11982
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.218
_diffrn_reflns_theta_min         3.148
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.970
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62417
_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            'clear light colourless'
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0020(4)
_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   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     413
_refine_ls_number_reflns         6613
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0655
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0915P)^2^+0.3471P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1714
_refine_ls_wR_factor_ref         0.1980
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4796
_reflns_number_total             6613
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj02968b3.cif
_cod_data_source_block           pqj-9
_cod_depositor_comments          'Adding full bibliography for 7063434.cif.'
_cod_database_code               7063434
_shelx_shelxl_version_number     2018/3
_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), C11(H11), C40(H40)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C12(H12A,H12B), C13(H13A,H13B), C32(H32A,H32B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C4(H4), C5(H5), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19),
 C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C27(H27), C28(H28), C29(H29),
  C30(H30), C31(H31), C34(H34), C35(H35), C36(H36), C37(H37), C38(H38)
2.d Idealised Me refined as rotating group:
 C39(H39A,H39B,H39C), C41(H41A,H41B,H41C)
;
_shelx_res_checksum              1461
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.502
_oxdiff_exptl_absorpt_empirical_full_min 0.580