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_7061259
_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         'C24 H24 N2 O3 S'
_chemical_formula_sum            'C24 H24 N2 O3 S'
_chemical_formula_weight         420.53
_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_date             2020-10-13
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2021-10-04 deposited with the CCDC.	2022-01-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.792(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8021(8)
_cell_length_b                   14.8362(7)
_cell_length_c                   11.9060(5)
_cell_measurement_reflns_used    5763
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.6050
_cell_measurement_theta_min      2.2010
_cell_volume                     2074.08(19)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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_temperature      293(2)
_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    -77.00  98.00   1.00    5.67    --   11.16   0.00-120.00  175
  2  \w      8.00  36.00   1.00    5.67    --   11.16 -38.00 120.00   28
  3  \w    -67.00   2.00   1.00    5.67    --  -11.24 -38.00-180.00   69
  4  \w      1.00  27.00   1.00    5.67    --  -11.24 -99.00 -30.00   26
  5  \w      2.00  30.00   1.00    5.67    --  -11.24 -99.00   0.00   28
;
_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      -0.0425460000
_diffrn_orient_matrix_UB_12      -0.0339518000
_diffrn_orient_matrix_UB_13      -0.0044108000
_diffrn_orient_matrix_UB_21      0.0350183000
_diffrn_orient_matrix_UB_22      -0.0273957000
_diffrn_orient_matrix_UB_23      -0.0309773000
_diffrn_orient_matrix_UB_31      0.0247236000
_diffrn_orient_matrix_UB_32      -0.0195696000
_diffrn_orient_matrix_UB_33      0.0510615000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15549
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.010
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_min         2.200
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.266
_exptl_crystal_description       block
_exptl_crystal_F_000             835
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3645
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0426
_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^)+(0.0670P)^2^+0.4140P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1242
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2916
_reflns_number_total             3645
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj05031a2.cif
_cod_data_source_block           a201012a
_cod_depositor_comments
;

2025-03-04
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C11 H10 Cl0 N O S0.11'
_cod_original_formula_weight         175.76
_cod_original_formula_moiety         '0.44(C24 H24 N2 O3 S)'
_cod_original_formula_units_Z            9
_cod_original_cell_volume        2074.07(19)
_cod_database_code               7061259
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B),
 C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C21(H21), C22(H22), C23(H23), C24(H24)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2020-10-12
_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 1.403
_oxdiff_exptl_absorpt_empirical_full_min 0.714