Trisulfur Radical Anion (S3•−) Involved Sulfur Insertion Reaction of 1,3-Enynes: Sulfide Sources Control Chemoselective Synthesis of 2,3,5-trisubstituted Thiophenes and 3-thienyl Disulfides
Li, Jing-Hao; Huang, Qi; Rao, Weidong; Wang, Shun-Yi; Ji, Shun-Jun; Chemical Communications  (2019) –; doi:10.1039/C9CC03604K

data_7123634
_publ_section_title
;
 Trisulfur Radical Anion (S3&#x2022;&#x2212;) Involved Sulfur Insertion
 Reaction of 1,3-Enynes: Sulfide Sources Control Chemoselective Synthesis
 of 2,3,5-trisubstituted Thiophenes and 3-thienyl Disulfides
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC03604K
_journal_year                    2019
_chemical_formula_moiety         '0.08(C34 H26 S4)'
_chemical_formula_sum            'C2.615 H2 S0.308'
_chemical_formula_weight         43.30
_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'
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-03-06 deposited with the CCDC.    2019-06-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.737(6)
_cell_angle_gamma                90
_cell_formula_units_Z            52
_cell_length_a                   15.8519(8)
_cell_length_b                   13.5230(7)
_cell_length_c                   14.0507(7)
_cell_measurement_reflns_used    5348
_cell_measurement_temperature    213.00(10)
_cell_measurement_theta_max      29.9840
_cell_measurement_theta_min      3.4420
_cell_volume                     2797.8(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      213.00(10)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.9988
_diffrn_measured_fraction_theta_max 0.9988
_diffrn_measurement_details
;
  1 omega   67.00   95.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       15.3991  178.0000    0.0000 28

  2 omega  -98.00  -58.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3366 -178.0000    0.0000 40

  3 omega  -90.00  -56.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3366  178.0000 -150.0000 34

  4 omega  -25.00   16.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3366  -99.0000  -30.0000 41

  5 omega  -25.00   19.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3366  -99.0000  150.0000 44

  6 omega  -10.00   44.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3366   37.0000 -180.0000 54

  7 omega -101.00  -68.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3366 -178.0000  -90.0000 33
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0007616000
_diffrn_orient_matrix_UB_12      0.0113522000
_diffrn_orient_matrix_UB_13      0.0495975000
_diffrn_orient_matrix_UB_21      0.0293067000
_diffrn_orient_matrix_UB_22      0.0404919000
_diffrn_orient_matrix_UB_23      0.0030705000
_diffrn_orient_matrix_UB_31      -0.0382570000
_diffrn_orient_matrix_UB_32      0.0312809000
_diffrn_orient_matrix_UB_33      -0.0220301000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20373
_diffrn_reflns_theta_full        24.9991
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.91
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.363
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78298
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_density_diffrn    1.3361
_exptl_crystal_description       block
_exptl_crystal_F_000             1178.3444
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.3680
_refine_diff_density_min         -0.3318
_refine_diff_density_rms         0.0620
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             7.0038
_refine_ls_goodness_of_fit_ref   1.0669
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    48
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4925
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0669
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1313
_refine_ls_wR_factor_ref         0.1446
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              17
_reflns_limit_h_min              -18
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                4075
_reflns_number_total             4925
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c9cc03604k2.cif
_cod_data_source_block           G180414A
_cod_database_code               7123634
_chemical_oxdiff_formula         'C H S O'
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C34(H34), C17(H17), C30(H30), C13(H13), C31(H31), C32(H32), C33(H33),
 C23(H23), C6(H6), C16(H16), C19(H19), C15(H15), C22(H22), C14(H14), C2(H2),
 C5(H5), C21(H21), C3(H3), C4(H4), C20(H20)
2.b Idealised Me refined as rotating group:
 C28(H28a,H28b,H28c), C11(H11a,H11b,H11c)
;
_olex2_submission_special_instructions 'No special instructions were received'