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_7131469
_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 O2 S'
_chemical_formula_sum            'C23 H25 N3 O2 S'
_chemical_formula_weight         407.52
_space_group_crystal_system      tetragonal
_space_group_IT_number           82
_space_group_name_Hall           'I -4'
_space_group_name_H-M_alt        'I -4'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.8691(8)
_cell_length_b                   20.8691(8)
_cell_length_c                   10.3768(6)
_cell_measurement_reflns_used    4440
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.4150
_cell_measurement_theta_min      2.1970
_cell_volume                     4519.3(4)
_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  (Sheldrick, 2015)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.870
_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     49.00  76.00   1.00    2.50    --   12.05  38.00-180.00   27
  2  \w    -20.00  63.00   1.00    2.50    --   12.05  77.00-120.00   83
  3  \w     -2.00  23.00   1.00    2.50    --   11.90  77.00   0.00   25
;
_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      0.0007835000
_diffrn_orient_matrix_UB_12      0.0116515000
_diffrn_orient_matrix_UB_13      -0.0641355000
_diffrn_orient_matrix_UB_21      -0.0055058000
_diffrn_orient_matrix_UB_22      0.0315732000
_diffrn_orient_matrix_UB_23      0.0229191000
_diffrn_orient_matrix_UB_31      0.0335286000
_diffrn_orient_matrix_UB_32      0.0049006000
_diffrn_orient_matrix_UB_33      0.0052782000
_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  0.0199
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.870
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8173
_diffrn_reflns_point_group_measured_fraction_full 0.927
_diffrn_reflns_point_group_measured_fraction_max 0.758
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.499
_diffrn_reflns_theta_min         2.192
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63642
_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    1.198
_exptl_crystal_description       block
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.712
_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 1389 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4774
_refine_ls_number_restraints     77
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0649
_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^)+(0.0921P)^2^+5.6492P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1675
_refine_ls_wR_factor_ref         0.1789
_reflns_Friedel_coverage         0.653
_reflns_Friedel_fraction_full    0.845
_reflns_Friedel_fraction_max     0.632
_reflns_number_gt                4068
_reflns_number_total             4774
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc00376k2.cif
_cod_data_source_block           226
_cod_depositor_comments
'Adding full bibliography for 7131469--7131471.cif.'
_cod_database_code               7131469
_shelx_shelxl_version_number     2017/1
_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. Restrained distances
 O3-C19
 1.39 with sigma of 0.01
 O3-C19 \\sim O2-C19
 with sigma of 0.02
3. Rigid bond restraints
 O3, C19, C23B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
O3 \\sim C19 \\sim C23B: within 2A with sigma of 0.002 and sigma for terminal
atoms of 0.004 within 2A
Uanis(C23B) \\sim Ueq: with sigma of 0.0006 and sigma for terminal atoms of
0.0012
Uanis(C19) = Uanis(O3) = Uanis(C23B)
Uanis(O2) = Uanis(C23) = Uanis(C16)
Uanis(C19) = Uanis(O2) = Uanis(C23)
5. Rigid body (RIGU) restrains
 O3, C19, C23B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 O2, C19, C23
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C15, C16, C17, C18, C19, C20
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.003
6. Others
 Sof(O3)=Sof(C23B)=Sof(H23D)=Sof(H23E)=Sof(H23F)=1-FVAR(1)
 Sof(O2)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=FVAR(1)
7.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
7.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C3(H3A), C4(H4), C5(H5), C17(H17), C18(H18), C20(H20)
7.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C),
 C23(H23A,H23B,H23C), C23B(H23D,H23E,H23F)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              59157
_shelx_hkl_checksum              37305
_shelx_fab_checksum              15588
_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 1.414
_oxdiff_exptl_absorpt_empirical_full_min 0.786