COS-triggered oxygen/sulfur exchange of isatins: chemoselective synthesis of functionalized isoindigos and spirothiopyrans <i>via</i> self-condensation and the thio-Diels-Alder reaction.
Chen, Wei; Zhou, Hui; Ren, Bai-Hao; Ren, Wei-Min; Lu, Xiao-Bing; Organic & biomolecular chemistry 20 (2022) 678–685; doi:10.1039/d1ob02157e

data_7158449
_publ_section_title
;
 COS-triggered oxygen/sulfur exchange of isatins: chemoselective synthesis
 of functionalized isoindigos and spirothiopyrans <i>via</i>
 self-condensation and the thio-Diels-Alder reaction.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              678
_journal_page_last               685
_journal_paper_doi               10.1039/d1ob02157e
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C24 H30 N2 O2 Si2'
_chemical_formula_sum            'C24 H30 N2 O2 Si2'
_chemical_formula_weight         434.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc24wg3m
_audit_creation_date             2019-07-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-10-15 deposited with the CCDC.	2021-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.701(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.0825(8)
_cell_length_b                   6.2924(4)
_cell_length_c                   15.8782(10)
_cell_measurement_reflns_used    845
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      19.773
_cell_measurement_theta_min      3.087
_cell_volume                     1207.10(13)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_unetI/netI     0.0765
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5625
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.461
_diffrn_reflns_theta_min         1.686
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/3 (Bruker,2014/3) was used for absorption correction. wR2(int) was 0.0647 before and 0.0410 after correction. The Ratio of minimum to maximum transmission is 0.8218. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
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_exptl_crystal_description       block
_exptl_crystal_F_000             464
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.204
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_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2703
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.970
_refine_ls_R_factor_all          0.1250
_refine_ls_R_factor_gt           0.0537
_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^)+(0.0567P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1466
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1314
_reflns_number_total             2703
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02157e2.cif
_cod_data_source_block           19jul16a_0m
_cod_depositor_comments
'Adding full bibliography for 7158448--7158450.cif.'
_cod_database_code               7158449
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              64669
_olex2_submission_special_instructions 'No special instructions were received'