In(OTf)<sub>3</sub>-catalyzed formal (4 + 3) cycloaddition reactions of 3-benzylideneindoline-2-thiones with 2-indolylmethanols.
Wang, Xue-Long; Yang, Yi; Jiang, Yan; Organic & biomolecular chemistry 22 (2024) 5902–5906; doi:10.1039/d4ob00897a

data_7160018
_publ_section_title
;
 In(OTf)<sub>3</sub>-catalyzed formal (4 + 3) cycloaddition reactions of
 3-benzylideneindoline-2-thiones with 2-indolylmethanols.
;
_journal_issue                   29
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5902
_journal_page_last               5906
_journal_paper_doi               10.1039/d4ob00897a
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C36 H26 N2 S'
_chemical_formula_sum            'C36 H26 N2 S'
_chemical_formula_weight         518.65
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-11-02
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-05-29 deposited with the CCDC.	2024-07-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.7160(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.11660(10)
_cell_length_b                   13.15070(10)
_cell_length_c                   14.17090(10)
_cell_measurement_reflns_used    9031
_cell_measurement_temperature    100.00(16)
_cell_measurement_theta_max      74.0380
_cell_measurement_theta_min      3.1750
_cell_volume                     2600.35(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
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_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(16)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.968
_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    -33.00  18.00   0.50    0.50    --    0.00 -82.00-120.00  102
  2  \w    -24.00  30.00   0.50    0.50    --    0.00 -82.00-180.00  108
  3  \w    -16.00  64.00   0.50    0.50    --    0.00  38.00   0.00  160
  4  \w    -45.00 -12.00   0.50    0.50    --    0.00 -77.00 -30.00   66
  5  \w      6.00 127.00   0.50    0.50    --   95.80 -82.00  90.00  242
  6  \w     80.00 170.00   0.50    0.50    --   95.80  45.00-150.00  180
  7  \w     21.00 114.00   0.50    0.50    --   95.80 -45.00 -60.00  186
  8  \w    139.00 185.00   0.50    0.50    --   95.80  45.00-180.00   92
  9  \w      8.00 109.00   0.50    0.50    --   95.80 -61.00  90.00  202
 10  \w     21.00 111.00   0.50    0.50    --   95.80 -61.00 -60.00  180
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0299614000
_diffrn_orient_matrix_UB_12      -0.0537537000
_diffrn_orient_matrix_UB_13      -0.0965234000
_diffrn_orient_matrix_UB_21      0.1001343000
_diffrn_orient_matrix_UB_22      0.0199603000
_diffrn_orient_matrix_UB_23      -0.0266756000
_diffrn_orient_matrix_UB_31      0.0354995000
_diffrn_orient_matrix_UB_32      -0.1021494000
_diffrn_orient_matrix_UB_33      0.0455263000
_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  0.0237
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13984
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.327
_diffrn_reflns_theta_min         4.119
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.318
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.627
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5136
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0391
_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^)+(0.0466P)^2^+1.7750P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1013
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4793
_reflns_number_total             5136
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00897a2.cif
_cod_data_source_block           wxl-3
_cod_depositor_comments          'Adding full bibliography for 7160018.cif.'
_cod_database_code               7160018
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N S'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13),
  C14(H14), C15(H15), C19(H19), C20(H20), C21(H21), C22(H22), C26(H26),
 C27(H27), C28(H28), C29(H29), C30(H30), C32(H32), C33(H33), C34(H34), C35(H35),
  C36(H36)
;
_shelx_res_checksum              96882
_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 1.462
_oxdiff_exptl_absorpt_empirical_full_min 0.728