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_7131471
_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         'C24 H25 N2 O S'
_chemical_formula_sum            'C24 H25 N2 O S'
_chemical_formula_weight         389.52
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                78.299(5)
_cell_angle_beta                 84.219(5)
_cell_angle_gamma                85.023(5)
_cell_formula_units_Z            2
_cell_length_a                   7.4539(5)
_cell_length_b                   9.8480(6)
_cell_length_c                   14.0220(9)
_cell_measurement_reflns_used    3576
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.4720
_cell_measurement_theta_min      3.1960
_cell_volume                     1000.46(11)
_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 0.997
_diffrn_measured_fraction_theta_max 0.966
_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     14.00 114.00   1.00    1.00    --   40.73  57.00 -60.00  100
  2  \w     92.00 177.00   1.00    1.00    --  106.95  30.00 -30.00   85
  3  \w    143.00 178.00   1.00    1.00    --  106.95  15.00 -90.00   35
  4  \w    109.00 161.00   1.00    1.00    --  106.95 125.00 -90.00   52
  5  \w     90.00 117.00   1.00    1.00    --  106.95  15.00 -90.00   27
  6  \w     61.00  89.00   1.00    1.00    --  106.95  15.00 -90.00   28
  7  \w     40.00 135.00   1.00    1.00    --  106.95 -61.00-120.00   95
  8  \w     83.00 113.00   1.00    1.00    --  106.95-125.00-180.00   30
  9  \w     41.00  68.00   1.00    1.00    --  106.95-125.00-180.00   27
 10  \w     28.00 109.00   1.00    1.00    --  106.95 -95.00-150.00   81
 11  \w     32.00 140.00   1.00    1.00    --  106.95 -77.00   0.00  108
 12  \w     80.00 120.00   1.00    1.00    --  106.95-125.00  30.00   40
 13  \w     56.00 118.00   1.00    1.00    --  106.95 -30.00 150.00   62
 14  \w     32.00 133.00   1.00    1.00    --  106.95 -30.00 -30.00  101
 15  \w    -64.00  22.00   1.00    1.00    --  -40.73  57.00  90.00   86
 16  \w    -64.00  35.00   1.00    1.00    --  -40.73  77.00-180.00   99
 17  \w    -82.00 -38.00   1.00    1.00    --  -40.73 125.00 -30.00   44
;
_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      0.1451477000
_diffrn_orient_matrix_UB_12      0.0492890000
_diffrn_orient_matrix_UB_13      -0.0831618000
_diffrn_orient_matrix_UB_21      -0.0895487000
_diffrn_orient_matrix_UB_22      0.1488079000
_diffrn_orient_matrix_UB_23      -0.0126116000
_diffrn_orient_matrix_UB_31      0.1194471000
_diffrn_orient_matrix_UB_32      0.0326610000
_diffrn_orient_matrix_UB_33      0.0748711000
_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  0.0329
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6641
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.657
_diffrn_reflns_theta_min         3.230
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.558
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70759
_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    1.293
_exptl_crystal_description       block
_exptl_crystal_F_000             414
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.739
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3903
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0530
_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^)+(0.0709P)^2^+0.9513P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1462
_refine_ls_wR_factor_ref         0.1523
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3371
_reflns_number_total             3903
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc00376k2.cif
_cod_data_source_block           d151
_cod_depositor_comments
'Adding full bibliography for 7131469--7131471.cif.'
_cod_database_code               7131471
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.835
_shelx_estimated_absorpt_t_min   0.800
_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. Rigid body (RIGU) restrains
 C12, C13, C14
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
3.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C4(H4), C5(H5), C16(H16), C17(H17), C18(H18), C19(H19)
3.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              13008
_shelx_hkl_checksum              11207
_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 1.676
_oxdiff_exptl_absorpt_empirical_full_min 0.538