Copper-Catalyzed Aerobic Oxidative [3+2] Annulation for the Synthesis of 5-Amino/Imino-Substituted 1,2,4-Thiadiazoles through C-N/N-S Bond Formation.
Yu, Wentao; Huang, Yubing; Li, Jianxiao; Tang, Xiaodong; Wu, Wanqing; Jiang, Huanfeng; The Journal of organic chemistry 83 (2018) 9334–9343; doi:10.1021/acs.joc.8b01292

data_4035312
_publ_section_title
;
 Copper-Catalyzed Aerobic Oxidative [3+2] Annulation for the Synthesis of
 5-Amino/Imino-Substituted 1,2,4-Thiadiazoles through C-N/N-S Bond
 Formation.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9334
_journal_page_last               9343
_journal_paper_doi               10.1021/acs.joc.8b01292
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C8 H9 N3 S'
_chemical_formula_sum            'C8 H9 N3 S'
_chemical_formula_weight         179.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-04-25
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.913(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.9658(3)
_cell_length_b                   17.1192(13)
_cell_length_c                   12.3386(11)
_cell_measurement_reflns_used    2622
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.8430
_cell_measurement_theta_min      4.7330
_cell_volume                     836.60(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -32.00  -4.00   1.00    3.37    --   11.90 -37.00   0.00   28
  2  \w      2.00  86.00   1.00    3.37    --   11.90  37.00 120.00   84
  3  \w    -19.00  64.00   1.00    3.37    --   11.90  77.00 -60.00   83
  4  \w     -8.00  85.00   1.00    3.37    --   11.90  37.00-150.00   93
  5  \w     41.00  80.00   1.00    3.37    --   11.90-178.00  90.00   39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0065639000
_diffrn_orient_matrix_UB_12      -0.0241644000
_diffrn_orient_matrix_UB_13      -0.0465707000
_diffrn_orient_matrix_UB_21      -0.1093557000
_diffrn_orient_matrix_UB_22      -0.0271739000
_diffrn_orient_matrix_UB_23      0.0237335000
_diffrn_orient_matrix_UB_31      -0.1415300000
_diffrn_orient_matrix_UB_32      0.0198455000
_diffrn_orient_matrix_UB_33      -0.0242122000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.875
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6675
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.593
_diffrn_reflns_theta_min         3.514
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.329
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         2060
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0421
_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^)+(0.0371P)^2^+0.4487P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.0932
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1809
_reflns_number_total             2060
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01292_si_002.cif
_cod_data_source_block           exp_420
_cod_database_code               4035312
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.934
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C1(H1), C2(H2)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_olex2_date_sample_data_collection 2017-04-24
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.352
_oxdiff_exptl_absorpt_empirical_full_min 0.728