Thiocyanate promoted difunctionalization and cyclization of unsaturated C–C bonds to construct 1-sulfur-2-nitrogen-functionalized alkenes and 2-thiocyanate indolines
Qin, Hong; Chen, Feng; Du, Jinze; Yang, Xiaobing; Huang, Yiping; Zhu, Kai; Yue, Changhai; Fang, Zheng; Guo, Kai; Organic & Biomolecular Chemistry 22 (2024) 1213–1218; doi:10.1039/D3OB01864D

data_7159771
_publ_section_title
;
 Thiocyanate promoted difunctionalization and cyclization of unsaturated
 C--C bonds to construct 1-sulfur-2-nitrogen-functionalized alkenes and
 2-thiocyanate indolines
;
_journal_issue                   6
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              1213
_journal_page_last               1218
_journal_paper_doi               10.1039/D3OB01864D
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C26 H23 N3 O2 S3'
_chemical_formula_sum            'C26 H23 N3 O2 S3'
_chemical_formula_weight         505.65
_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             2021-04-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-11-19 deposited with the CCDC.	2024-01-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.0630(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.0220(3)
_cell_length_b                   11.6268(2)
_cell_length_c                   22.3898(3)
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.916
_cell_measurement_theta_min      3.871
_cell_volume                     4982.74(13)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      173.0
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            20255
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.954
_diffrn_reflns_theta_min         3.870
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.920
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1217 before and 0.0452 after correction. The Ratio of minimum to maximum transmission is 0.8183. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       block
_exptl_crystal_F_000             2112
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4675
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0334
_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^)+(0.0326P)^2^+5.3909P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0845
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4184
_reflns_number_total             4675
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01864d2.cif
_cod_data_source_block           2104011479_0m
_cod_depositor_comments          'Adding full bibliography for 7159771.cif.'
_cod_database_code               7159771
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.910
_shelx_estimated_absorpt_t_min   0.877
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C15(H15),
 C16(H16), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              72858
_shelx_hkl_checksum              45321
_olex2_submission_special_instructions 'No special instructions were received'