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_7158450
_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         'C16 H12 N4 O2'
_chemical_formula_sum            'C16 H12 N4 O2'
_chemical_formula_weight         292.30
_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
_audit_block_doi                 10.5517/ccdc.csd.cc24wg4n
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_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-10-16 deposited with the CCDC.	2021-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
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_cell_angle_gamma                90
_cell_formula_units_Z            8
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_cell_length_b                   8.6862(14)
_cell_length_c                   15.721(3)
_cell_measurement_reflns_used    1844
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.108
_cell_measurement_theta_min      2.571
_cell_volume                     2640.6(8)
_computing_cell_refinement       'SAINT V8.32B (?, 2016)'
_computing_data_reduction        'SAINT V8.32B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0652
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3348
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.653
_diffrn_reflns_theta_min         2.106
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4750
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'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1117 before and 0.0699 after correction. The Ratio of minimum to maximum transmission is 0.6370. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.470
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_refine_diff_density_max         0.599
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.124
_refine_ls_extinction_coef       0.0040(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3348
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.1352
_refine_ls_R_factor_gt           0.0945
_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^)+(0.1504P)^2^+1.6362P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2506
_refine_ls_wR_factor_ref         0.2786
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2140
_reflns_number_total             3348
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02157e2.cif
_cod_data_source_block           19oct22a_0m_tw
_cod_depositor_comments
'Adding full bibliography for 7158448--7158450.cif.'
_cod_database_code               7158450
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.609(6)
 0.391(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15)
3.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              16827
_olex2_submission_special_instructions 'No special instructions were received'