I2/CuCl2-Promoted One-Pot Three-Component Synthesis of Aliphatic or Aromatic Substituted 1,2,3-Thiadiazoles
Wang, Can; Geng, Xiao; Zhao, Peng; Zhou, You; Wu, Yan-Dong; Cui, Yan-Fang; Wu, An-Xin; Chemical Communications  (2019) –; doi:10.1039/C9CC04254G

data_7123685
_publ_section_title
;
 I2/CuCl2-Promoted One-Pot Three-Component Synthesis of Aliphatic or
 Aromatic Substituted 1,2,3-Thiadiazoles
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC04254G
_journal_year                    2019
_chemical_formula_moiety         'C23 H32 N2 O2 S'
_chemical_formula_sum            'C23 H32 N2 O2 S'
_chemical_formula_weight         400.56
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-04-26
_audit_creation_method
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_audit_update_record
;
2019-05-31 deposited with the CCDC.    2019-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.334(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6526(5)
_cell_length_b                   7.4265(4)
_cell_length_c                   30.2283(16)
_cell_measurement_reflns_used    9993
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      70.94
_cell_measurement_theta_min      2.94
_cell_volume                     2157.5(2)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            11111
_diffrn_reflns_point_group_measured_fraction_full 0.937
_diffrn_reflns_point_group_measured_fraction_max 0.893
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.385
_diffrn_reflns_theta_min         2.936
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.486
_exptl_absorpt_correction_T_max  0.7534
_exptl_absorpt_correction_T_min  0.3234
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
; 
 Flack x determined using 1552 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.086(8)
_refine_ls_extinction_coef       0.0080(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3764
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0408
_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^)+(0.0679P)^2^+0.5479P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1140
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_full    0.886
_reflns_Friedel_fraction_max     0.832
_reflns_number_gt                3729
_reflns_number_total             3764
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc04254g2.cif
_cod_data_source_block           cu_190425_0m
_cod_database_code               7123685
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.842
_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. Restrained distances 
 C22-C23 = C22'-C23' 
 1.51 with sigma of 0.01 
 C22-O2 = C22'-O2' 
 1.25 with sigma of 0.01 
3. Restrained planarity 
 C22, C23, O1, O2 
 with sigma of 0.1 
4. Uiso/Uaniso restraints and constraints 
Uanis(C22) = Uanis(C22') 
Uanis(O2) = Uanis(O2') 
Uanis(C23) = Uanis(C23') 
5. Others 
 Sof(C22')=Sof(C23')=Sof(H23D)=Sof(H23E)=Sof(H23F)=Sof(O2')=1-FVAR(1) 
 Sof(C22)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=Sof(O2)=FVAR(1) 
6.a Ternary CH refined with riding coordinates: 
 C3(H3), C8(H8), C9(H9), C14(H14), C17(H17) 
6.b Secondary CH2 refined with riding coordinates: 
 C1(H1A,H1B), C2(H2A,H2B), C4(H4A,H4B), C7(H7A,H7B), C11(H11A,H11B), C12(H12A, 
 H12B), C15(H15A,H15B), C16(H16A,H16B) 
6.c Aromatic/amide H refined with riding coordinates: 
 C6(H6), C19(H19) 
6.d Idealised Me refined as rotating group: 
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C23'(H23D,H23E, 
 H23F) 
;
_shelx_res_checksum              63261
_olex2_submission_special_instructions 'No special instructions were received'