Diastereoselective three-component 1,3-dipolar cycloaddition: concise synthesis of functionalized tetrahydrocarboline-fused spirooxindoles.
Wang, Yongchao; Zheng, Lihua; Zi, Rongmei; Niu, Yanqin; Yang, Shuyuan; Hu, Donghua; Dong, Jianwei; Organic & biomolecular chemistry 23 (2025) 2941–2953; doi:10.1039/d4ob02099e

data_7160381
_publ_section_title
;
 Diastereoselective three-component 1,3-dipolar cycloaddition: concise
 synthesis of functionalized tetrahydrocarboline-fused spirooxindoles.
;
_journal_issue                   12
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2941
_journal_page_last               2953
_journal_paper_doi               10.1039/d4ob02099e
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C36 H27 N5 O6, C H4 O'
_chemical_formula_sum            'C37 H31 N5 O7'
_chemical_formula_weight         657.69
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     direct
_audit_creation_date             2024-05-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-11-20 deposited with the CCDC.	2025-02-14 downloaded from the CCDC.
;
_cell_angle_alpha                71.410(6)
_cell_angle_beta                 81.660(5)
_cell_angle_gamma                72.117(6)
_cell_formula_units_Z            2
_cell_length_a                   11.1970(7)
_cell_length_b                   11.5741(7)
_cell_length_c                   13.8720(8)
_cell_measurement_reflns_used    11122
_cell_measurement_temperature    100
_cell_measurement_theta_max      78.2870
_cell_measurement_theta_min      3.3420
_cell_volume                     1619.40(19)
_computing_cell_refinement       'CrysAlisPro 1.171.43.118a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.118a 64-bit (release 27-03-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.118a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9659
_diffrn_measured_fraction_theta_max 0.9659
_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   -126.00 -32.00   0.50    0.20    -- -105.00 144.00 -76.80  188
  2  \w   -112.00 -35.00   0.50    0.20    -- -105.00 125.00  60.00  154
  3  \w   -126.00 -32.00   0.50    0.20    -- -105.00 144.00 109.51  188
  4  \w   -126.00 -32.00   0.50    0.20    -- -105.00 144.00 109.51  188
  5  \w   -112.00 -35.00   0.50    0.20    -- -105.00 125.00 150.00  154
  6  \w   -112.00 -35.00   0.50    0.20    -- -105.00 125.00  30.00  154
  7  \w   -112.00 -35.00   0.50    0.20    -- -105.00 125.00-180.00  154
  8  \w    -26.00  28.00   0.50    0.05    --  -47.76  19.00 -60.00  108
  9  \w    -67.00  25.00   0.50    0.05    --  -47.76  66.00 143.00  184
 10  \w    -79.00 -32.00   0.50    0.20    -- -105.00  66.00 143.00   94
 11  \w    -71.00 -32.00   0.50    0.20    -- -105.00  61.00 -30.00   78
 12  \w    -71.00 -32.00   0.50    0.20    -- -105.00  61.00-180.00   78
 13  \w   -175.00 -90.00   0.50    0.20    -- -105.00 -50.00-110.46  170
 14  \w   -121.00 -28.00   0.50    0.05    --  -47.76 -66.00   9.00  186
 15  \w   -175.00 -86.00   0.50    0.20    -- -105.00 -65.00  81.11  178
 16  \w   -175.00 -86.00   0.50    0.20    -- -105.00 -65.00  81.11  178
 17  \w   -175.00 -86.00   0.50    0.20    -- -105.00 -66.00   9.00  178
 18  \w   -175.00 -83.00   0.50    0.20    -- -105.00 -95.00-120.00  184
 19  \w   -175.00 -83.00   0.50    0.20    -- -105.00 -95.00-120.00  184
 20  \w   -118.00 -73.00   0.50    0.05    --  -47.76-125.00-180.00   90
 21  \w   -118.00 -73.00   0.50    0.05    --  -47.76-125.00 -90.00   90
 22  \w   -118.00 -73.00   0.50    0.05    --  -47.76-125.00  30.00   90
 23  \w     13.00  95.00   0.50    0.05    --   47.76-125.00-120.00  164
 24  \w     40.00 106.00   0.50    0.20    --  112.38 -95.00-150.00  132
 25  \w     43.00 111.00   0.50    0.20    --  112.38-125.00 -30.00  136
 26  \w     40.00 106.00   0.50    0.20    --  112.38 -95.00-120.00  132
 27  \w     43.00 111.00   0.50    0.20    --  112.38-125.00 -30.00  136
 28  \w     40.00 106.00   0.50    0.20    --  112.38 -95.00 -90.00  132
 29  \w     45.00  96.00   0.50    0.20    --  112.38-125.00   0.00  102
 30  \w     40.00 106.00   0.50    0.20    --  112.38 -95.00   0.00  132
 31  \w     43.00 111.00   0.50    0.20    --  112.38-125.00  90.00  136
 32  \w     40.00 106.00   0.50    0.20    --  112.38 -95.00 120.00  132
 33  \w    -24.00  67.00   0.50    0.05    --   47.76 -66.00   9.00  182
 34  \w    -28.00  26.00   0.50    0.05    --   47.76 -19.00  30.00  108
 35  \w     40.00  79.00   0.50    0.20    --  112.38 -66.00   9.00   78
 36  \w     40.00  71.00   0.50    0.20    --  112.38 -61.00 -30.00   62
 37  \w     95.00 176.00   0.50    0.20    --  112.38  15.00 -60.00  162
 38  \w     98.00 175.00   0.50    0.20    --  112.38  45.00  60.00  154
 39  \w     98.00 176.00   0.50    0.20    --  112.38  45.00  90.00  156
 40  \w     98.00 176.00   0.50    0.20    --  112.38  45.00  90.00  156
 41  \w     93.00 176.00   0.50    0.20    --  112.38  66.00 143.00  166
 42  \w     29.00 121.00   0.50    0.05    --   47.76  66.00 143.00  184
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1325042000
_diffrn_orient_matrix_UB_12      -0.0937798000
_diffrn_orient_matrix_UB_13      0.0102841000
_diffrn_orient_matrix_UB_21      -0.0535256000
_diffrn_orient_matrix_UB_22      -0.1018472000
_diffrn_orient_matrix_UB_23      0.0792211000
_diffrn_orient_matrix_UB_31      -0.0231553000
_diffrn_orient_matrix_UB_32      -0.0469785000
_diffrn_orient_matrix_UB_33      -0.0859317000
_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  0.0430
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            32346
_diffrn_reflns_theta_full        78.8690
_diffrn_reflns_theta_max         78.87
_diffrn_reflns_theta_min         3.37
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.783
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78343
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.118a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.3487
_exptl_crystal_description       block
_exptl_crystal_F_000             690.3571
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.5093
_refine_diff_density_min         -0.5923
_refine_diff_density_rms         0.0507
_refine_ls_d_res_high            0.7857
_refine_ls_d_res_low             13.1303
_refine_ls_goodness_of_fit_ref   1.0427
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    58
_refine_ls_number_parameters     444
_refine_ls_number_reflns         6751
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0427
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0591
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1035P)^2^+0.4175P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1752
_refine_ls_wR_factor_ref         0.1839
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -13
_reflns_limit_k_max              14
_reflns_limit_k_min              -13
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                5587
_reflns_number_total             6751
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4ob02099e2.cif
_cod_data_source_block           b
_cod_depositor_comments          'Adding full bibliography for 7160381.cif.'
_cod_database_code               7160381
_chemical_oxdiff_formula         chon
_diffrn_oxdiff_digest_frames
;
01717bded2eb690d9a4f63630449148f2a059927e28
;
_diffrn_oxdiff_digest_hkl
;
0173c4f472cdc8bb2f311d58dc01789ee8820c
;
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C25(H25a,H25b), C32(H32a,H32b)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C29(H29), C33(H33), C21(H21), C31(H31), C37(H37), C39(H39),
 C40(H40), C45(H45a), C49(H49), C47(H47), C46(H46), C34(H34), C44(H44a),
 C43(H43), C38(H38), N44(H44), N45(H45), C13(H13), C24(H24)
2.d Idealised Me refined as rotating group:
 C48(H48a,H48b,H48c)
2.e Idealised tetrahedral OH refined as rotating group:
 O48(H48)
;
_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 1.276
_oxdiff_exptl_absorpt_empirical_full_min 0.775