Cycloaddition/Electrocyclic Ring Opening Sequence between Alkynyl Sulfides and Azodicarboxylates To Provide <i>N</i>,<i>N</i>-Dicarbamoyl 2-Iminothioimidates.
Narangoda, Chandima J.; Kakeshpour, Tayeb; Lex, Timothy R.; Redden, Brandon K.; Moore, Madelyn A.; Frank, Emma M.; McMillen, Colin D.; Wiskur, Sheryl L.; Kitaygorodskiy, Alex; Jackson, James E.; Whitehead, Daniel C.; The Journal of organic chemistry 84 (2019) 9734–9743; doi:10.1021/acs.joc.9b01515

data_4034384
_publ_section_title
;
 Cycloaddition/Electrocyclic Ring Opening Sequence between Alkynyl
 Sulfides and Azodicarboxylates To Provide <i>N</i>,<i>N</i>-Dicarbamoyl
 2-Iminothioimidates.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9734
_journal_page_last               9743
_journal_paper_doi               10.1021/acs.joc.9b01515
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C20 H20 N2 O4 S'
_chemical_formula_weight         384.44
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 102.063(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6872(9)
_cell_length_b                   12.2430(12)
_cell_length_c                   16.6225(15)
_cell_measurement_reflns_used    9958
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.72
_cell_volume                     1927.9(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      140(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            37901
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.499
_diffrn_reflns_theta_min         3.556
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9635
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker, SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.087
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3982
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0331
_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^)+(0.0312P)^2^+1.0025P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0800
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3491
_reflns_number_total             3982
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01515_si_006.cif
_cod_data_source_block           6g
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4034384
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.954
_shelx_estimated_absorpt_t_max   0.983
_shelx_res_checksum              44115
_shelx_hkl_checksum              31469