[4 + 1] Cycloaddition Reaction of α,β-Alkynic Hydrazones and KSCN under Transition-Metal-Free Conditions: Synthesis of N-Iminoisothiazolium Ylides.
Liu, Bei-Bei; Cao, Wen-Bin; Wang, Fei; Wang, Shun-Yi; Ji, Shun-Jun; The Journal of organic chemistry 83 (2018) 11118–11124; doi:10.1021/acs.joc.8b01725

data_4035642
_publ_section_title
;
 [4 + 1] Cycloaddition Reaction of \a,\b-Alkynic Hydrazones and KSCN under
 Transition-Metal-Free Conditions: Synthesis of N-Iminoisothiazolium
 Ylides.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11118
_journal_page_last               11124
_journal_paper_doi               10.1021/acs.joc.8b01725
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C22 H18 N2 O2 S2'
_chemical_formula_weight         406.5
_space_group_crystal_system      tetragonal
_space_group_IT_number           114
_space_group_name_Hall           'P -4 2n'
_space_group_name_H-M_alt        'P -4 21 c'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.5225(4)
_cell_length_b                   17.5225(4)
_cell_length_c                   13.2022(7)
_cell_measurement_reflns_used    9900
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.64
_cell_measurement_theta_min      2.32
_cell_volume                     4053.6(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0931
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            54740
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_min         1.644
_exptl_absorpt_coefficient_mu    0.283
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       block
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Flack x determined using 1654 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.37(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4653
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0380
_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^)+(0.0491P)^2^+1.5934P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.1086
_reflns_Friedel_coverage         0.804
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3998
_reflns_number_total             4646
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01725_si_001.cif
_cod_data_source_block           1122-2
_cod_database_code               4035642
_shelxl_version_number           2013-2
_shelx_res_checksum              56853
_shelx_hkl_checksum              52711