Direct access to thieno[3,4-b]thiophenes via elemental sulfur-promoted sulfurative tetramerization of acetophenones
Nguyen, Thanh Binh; Retailleau, Pascal; Chemical Communications  (2022) –; doi:10.1039/D2CC05539B

data_7130980
_publ_section_title
;
 Direct access to thieno[3,4-b]thiophenes via elemental sulfur-promoted
 sulfurative tetramerization of acetophenones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC05539B
_journal_year                    2022
_chemical_formula_moiety         'C32 H20 O2 S2'
_chemical_formula_sum            'C32 H20 O2 S2'
_chemical_formula_weight         500.60
_chemical_name_systematic
;
'(3,6-diphenylthieno[3,4-b]thiophene-2,4-diyl)bis(phenylmethanone)'
;
_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     other
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-08-02
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2022-08-02 deposited with the CCDC.	2022-11-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.435(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0865(6)
_cell_length_b                   12.4636(6)
_cell_length_c                   17.3007(8)
_cell_measurement_reflns_used    9144
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.0020
_cell_measurement_theta_min      2.4970
_cell_volume                     2523.9(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_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     -4.00  55.00   0.50   17.50    --    1.00  37.00  53.00  118
  2  \w      3.00  28.00   0.50   17.50    --   -1.30  37.00  53.00   50
  3  \w     47.00  73.00   0.50   17.50    --    1.00  38.00   0.00   52
  4  \w    -28.00  72.00   0.50   17.50    --    1.00  57.00 -90.00  200
  5  \w     32.00  86.00   0.50   17.50    --    1.00  57.00-180.00  108
  6  \w    -28.00  31.00   0.50   17.50    --    1.00  57.00   0.00  118
  7  \w    -33.00  20.00   0.50   17.50    --   -1.30  38.00-180.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0187004000
_diffrn_orient_matrix_UB_12      -0.0242243000
_diffrn_orient_matrix_UB_13      0.0381337000
_diffrn_orient_matrix_UB_21      0.0575208000
_diffrn_orient_matrix_UB_22      0.0110770000
_diffrn_orient_matrix_UB_23      -0.0001181000
_diffrn_orient_matrix_UB_31      -0.0036651000
_diffrn_orient_matrix_UB_32      0.0502792000
_diffrn_orient_matrix_UB_33      0.0184015000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            34392
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_min         2.387
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.406
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_description       'diamond-like tab'
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5513
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0434
_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^)+(0.0489P)^2^+0.9654P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1166
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4286
_reflns_number_total             5513
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc05539b2.cif
_cod_data_source_block           B14502
_cod_database_code               7130980
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C32 H20 O2 S2'
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.932
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C9(H9), C26(H26), C28(H28), C19(H19), C25(H25), C29(H29), C16(H16),
 C32(H32), C22(H22), C24(H24), C30(H30), C17(H17), C18(H18), C10(H10), C23(H23),
  C13(H13), C31(H31), C12(H12), C11(H11)
;
_shelx_res_checksum              62767
_shelx_hkl_checksum              10269
_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 1.221
_oxdiff_exptl_absorpt_empirical_full_min 0.635