Fischer's base-triggered formal (3+2) cycloadditions with 3-isothiocyanato oxindoles as acceptor-donor synthons.
Liu, Xiong-Wei; Chen, Zi-Yue; Liu, Ren-Ming; Zhang, Wen-Hui; Pan, Bo-Wen; Zhou, Jian; Tian, You-Ping; Zhou, Ying; Liu, Xiong-Li; Chemical communications (Cambridge, England) 59 (2023) 4652–4655; doi:10.1039/d3cc00376k

data_7131470
_publ_section_title
;
 Fischer's base-triggered formal (3+2) cycloadditions with
 3-isothiocyanato oxindoles as acceptor-donor synthons.
;
_journal_issue                   31
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4652
_journal_page_last               4655
_journal_paper_doi               10.1039/d3cc00376k
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C23 H25 N3 O S'
_chemical_formula_sum            'C23 H25 N3 O S'
_chemical_formula_weight         391.52
_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
_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
;
2022-12-21 deposited with the CCDC.	2023-03-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.552(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.8625(12)
_cell_length_b                   8.7470(7)
_cell_length_c                   25.549(2)
_cell_measurement_reflns_used    4351
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      29.1320
_cell_measurement_theta_min      2.5700
_cell_volume                     4207.2(5)
_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      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.991
_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    -39.00  60.00   1.00    2.00    --  -11.27  57.00  90.00   99
  2  \w     43.00  69.00   1.00    2.00    --   11.90 178.00  90.00   26
  3  \w    -17.00  75.00   1.00    2.00    --   11.90  77.00-150.00   92
  4  \w    -79.00 -51.00   1.00    2.00    --  -11.27 -57.00 -60.00   28
;
_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      -0.0329818500
_diffrn_orient_matrix_UB_12      -0.0294217500
_diffrn_orient_matrix_UB_13      0.0073327000
_diffrn_orient_matrix_UB_21      -0.0170883500
_diffrn_orient_matrix_UB_22      0.0317132500
_diffrn_orient_matrix_UB_23      -0.0230225000
_diffrn_orient_matrix_UB_31      0.0063040000
_diffrn_orient_matrix_UB_32      -0.0685399000
_diffrn_orient_matrix_UB_33      -0.0137721000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            11218
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.164
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77799
_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    1.236
_exptl_crystal_description       block
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3688
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0399
_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^)+(0.0409P)^2^+3.4865P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.0971
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3137
_reflns_number_total             3688
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc00376k2.cif
_cod_data_source_block           b10
_cod_depositor_comments
'Adding full bibliography for 7131469--7131471.cif.'
_cod_original_cell_volume        4207.3(5)
_cod_database_code               7131470
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.975
_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
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C17(H17), C18(H18), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              6504
_shelx_hkl_checksum              76404
_shelx_fab_checksum              19476
_olex2_date_sample_data_collection 2022-10-08
_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 1.413
_oxdiff_exptl_absorpt_empirical_full_min 0.791