I2-Catalyzed Oxidative N-S Bond Formation: Metal-Free Regiospecific Synthesis of N-Fused and 3,4-Disubstituted 5-Imino-1,2,4-thiadiazoles.
Tumula, Nagaraju; Jatangi, Nagesh; Palakodety, Radha Krishna; Balasubramanian, Sridhar; Nakka, Mangarao; The Journal of organic chemistry 82 (2017) 5310–5316; doi:10.1021/acs.joc.7b00646

data_4032532
_publ_section_title
;
 I2-Catalyzed Oxidative N-S Bond Formation: Metal-Free Regiospecific
 Synthesis of N-Fused and 3,4-Disubstituted 5-Imino-1,2,4-thiadiazoles.
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_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5310
_journal_page_last               5316
_journal_paper_doi               10.1021/acs.joc.7b00646
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C18 H19 N3 S'
_chemical_formula_sum            'C18 H19 N3 S'
_chemical_formula_weight         309.42
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                92.86(4)
_cell_angle_beta                 95.13(7)
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_cell_formula_units_Z            2
_cell_length_a                   5.882(16)
_cell_length_b                   9.000(19)
_cell_length_c                   15.23(3)
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.38
_cell_measurement_theta_min      2.29
_cell_volume                     796(3)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2016)'
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_computing_structure_solution    '<i>SHELXT</i> (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
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_diffrn_reflns_limit_h_min       -7
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_diffrn_reflns_limit_l_min       -20
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_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.307
_diffrn_reflns_theta_min         2.282
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker,2016'
_exptl_crystal_colour            colorless
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_exptl_crystal_description       block
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_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.240
_refine_diff_density_max         0.643
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3949
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0401
_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^)+(0.0332P)^2^+0.5531P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.0990
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3624
_reflns_number_total             3949
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00646_si_003.cif
_cod_data_source_block           KA164_0m
_cod_database_code               4032532
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.919
_shelx_estimated_absorpt_t_max   0.953
_shelx_res_checksum              13154
_shelx_hkl_checksum              21693