Trimethylindolenines as C–N synthons for the assembly of spiro[oxindole-thioxoimidazolidine-indoline] hybrids in formal [3+2] cycloadditions
Zhang, Wen-Hui; Chen, Zi-Yue; Liu, Ren-Ming; Liu, Xiong-Wei; Pan, Bo-Wen; Zhou, Jian; Zhou, Ying; Tian, You-Ping; Liu, Xiong-Li; New Journal of Chemistry 47 (2023) 12296–12303; doi:10.1039/D3NJ00901G

data_1569258
_publ_section_title
;
 Trimethylindolenines as C--N synthons for the assembly of
 spiro[oxindole-thioxoimidazolidine-indoline] hybrids in formal [3+2]
 cycloadditions
;
_journal_issue                   26
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              12296
_journal_page_last               12303
_journal_paper_doi               10.1039/D3NJ00901G
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C21 H20 F N3 O S'
_chemical_formula_sum            'C21 H20 F N3 O S'
_chemical_formula_weight         381.46
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-09
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-12-28 deposited with the CCDC.	2023-05-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.0518(2)
_cell_length_b                   17.6500(4)
_cell_length_c                   26.8891(6)
_cell_measurement_reflns_used    9289
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.3810
_cell_measurement_theta_min      2.4870
_cell_volume                     3821.32(15)
_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 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_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    -82.00  39.00   1.00    1.00    --  -40.73  19.00 -60.00  121
  2  \w     23.00  97.00   1.00    1.00    --   40.73-125.00-120.00   74
  3  \w     94.00 178.00   1.00    1.06    --  106.95 125.00-150.00   84
  4  \w     34.00 121.00   1.00    1.06    --  106.95-125.00-180.00   87
  5  \w     74.00 178.00   1.00    1.06    --  106.95  77.00  60.00  104
  6  \w     98.00 178.00   1.00    1.06    --  106.95  84.00 -67.00   80
  7  \w     31.00 135.00   1.00    1.06    --  106.95 -30.00 -90.00  104
  8  \w     94.00 178.00   1.00    1.06    --  106.95 125.00  60.00   84
  9  \w     79.00 137.00   1.00    1.06    --  106.95  30.00 -60.00   58
;
_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      0.1013600000
_diffrn_orient_matrix_UB_12      0.0695028000
_diffrn_orient_matrix_UB_13      -0.0166854000
_diffrn_orient_matrix_UB_21      0.1339335000
_diffrn_orient_matrix_UB_22      -0.0188543000
_diffrn_orient_matrix_UB_23      0.0390094000
_diffrn_orient_matrix_UB_31      0.0918208000
_diffrn_orient_matrix_UB_32      -0.0492359000
_diffrn_orient_matrix_UB_33      -0.0385064000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            17499
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.576
_diffrn_reflns_theta_min         3.287
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.715
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54086
_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            'light yellow'
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       block
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3807
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0512
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0930P)^2^+1.5625P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1384
_refine_ls_wR_factor_ref         0.1418
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3497
_reflns_number_total             3807
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj00901g2.cif
_cod_data_source_block           9
_cod_depositor_comments          'Adding full bibliography for 1569258.cif.'
_cod_database_code               1569258
_shelx_shelxl_version_number     2017/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C12(H12), C14(H14), C15(H15)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C)
;
_shelx_res_checksum              27384
_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 1.458
_oxdiff_exptl_absorpt_empirical_full_min 0.646