Construction of 4-spiroannulated tetrahydroisoquinoline skeletons via a sequential ring opening of aziridines and Pictet–Spengler reaction
Xing, Siyang; Wang, Chenyu; Gao, Tingxuan; Wang, Yuhan; Wang, Hongzheng; Wang, Hanfei; Wang, Kui; Zhu, Bolin; New Journal of Chemistry 46 (2022) 2553–2558; doi:10.1039/D1NJ05031A

data_7061258
_publ_section_title
;
 Construction of 4-spiroannulated tetrahydroisoquinoline skeletons via a
 sequential ring opening of aziridines and Pictet--Spengler reaction
;
_journal_issue                   5
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              2553
_journal_page_last               2558
_journal_paper_doi               10.1039/D1NJ05031A
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C22 H27 N O3 S'
_chemical_formula_sum            'C22 H27 N O3 S'
_chemical_formula_weight         385.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-11-16
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2021-10-03 deposited with the CCDC.	2022-01-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.6470(16)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.5164(3)
_cell_length_b                   10.53615(13)
_cell_length_c                   23.0730(3)
_cell_measurement_reflns_used    11092
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.7060
_cell_measurement_theta_min      2.0430
_cell_volume                     3957.93(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2740
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -87.00  -6.00   1.00    1.00    --  -41.61 125.00 150.00   81
  2  \w    -70.00  -9.00   1.00    1.00    --  -41.61 125.00 -60.00   61
  3  \w    -48.00  30.00   1.00    1.00    --  -41.61  38.00 120.00   78
  4  \w   -115.00 -17.00   1.00    1.00    --  -41.61 -38.00 150.00   98
  5  \w     69.00  96.00   1.00    1.00    --   41.61  38.00-120.00   27
  6  \w     65.00  94.00   1.00    1.00    --   41.61-125.00  30.00   29
  7  \w    114.00 177.00   1.00    3.39    --  105.20 125.00-120.00   63
  8  \w    106.00 169.00   1.00    3.39    --  105.20  77.00  30.00   63
  9  \w     82.00 108.00   1.00    3.39    --  105.20  61.00-150.00   26
 10  \w     77.00 104.00   1.00    3.39    --  105.20  30.00 120.00   27
 11  \w     26.00 105.00   1.00    3.39    --  105.20 -94.00   0.00   79
 12  \w    105.00 178.00   1.00    3.39    --  105.20  77.00 150.00   73
 13  \w     33.00  65.00   1.00    3.39    --  105.20 -94.00  60.00   32
 14  \w     76.00 112.00   1.00    3.39    --  105.20  61.00-120.00   36
 15  \w     53.00 108.00   1.00    3.39    --  105.20 -45.00-150.00   55
 16  \w     77.00 154.00   1.00    3.39    --  105.20  30.00 -60.00   77
 17  \w    133.00 163.00   1.00    3.39    --  105.20  61.00-120.00   30
 18  \w    127.00 169.00   1.00    3.39    --  105.20  61.00-150.00   42
 19  \w    112.00 150.00   1.00    3.39    --  105.20  77.00-180.00   38
 20  \w     38.00  98.00   1.00    3.39    --  105.20 -94.00  90.00   60
 21  \w    115.00 153.00   1.00    3.39    --  105.20   0.00 120.00   38
 22  \w    124.00 175.00   1.00    3.39    --  105.20  30.00 120.00   51
 23  \w     50.00  91.00   1.00    3.39    --  105.20   0.00 120.00   41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0429347000
_diffrn_orient_matrix_UB_12      -0.0601715000
_diffrn_orient_matrix_UB_13      -0.0407367000
_diffrn_orient_matrix_UB_21      -0.0669855000
_diffrn_orient_matrix_UB_22      -0.1030591000
_diffrn_orient_matrix_UB_23      -0.0213683000
_diffrn_orient_matrix_UB_31      -0.0512150000
_diffrn_orient_matrix_UB_32      0.0844976000
_diffrn_orient_matrix_UB_33      -0.0551731000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            13253
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.020
_diffrn_reflns_theta_max         67.020
_diffrn_reflns_theta_min         4.123
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.627
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.587
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3541
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0414
_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^)+(0.0662P)^2^+4.0103P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1083
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3430
_reflns_number_total             3541
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj05031a2.cif
_cod_data_source_block           a201116a
_cod_original_cell_volume        3957.93(10)
_cod_database_code               7061258
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B),
 C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C17(H17), C18(H18), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C22(H22A,H22B,H22C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2020-11-16
_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 3.582
_oxdiff_exptl_absorpt_empirical_full_min 0.606