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_7130985
_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 H16 Br4 O2 S2'
_chemical_formula_sum            'C32 H16 Br4 O2 S2'
_chemical_formula_weight         816.229
_chemical_name_systematic
;
'(3,6-bis(3-bromophenyl)thieno[3,4-b]thiophene-2,4-diyl)bis
((3-bromophenyl)methanone)'
;
_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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-04-15
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-08-02 deposited with the CCDC.	2022-11-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.769(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9600(9)
_cell_length_b                   15.6784(9)
_cell_length_c                   15.0197(9)
_cell_measurement_reflns_used    11359
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.6400
_cell_measurement_theta_min      2.5810
_cell_volume                     2853.6(3)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.9969
_diffrn_measured_fraction_theta_max 0.9972
_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    -28.00  90.00   0.50   45.00    --    1.00  57.00  90.00  236
  2  \w    -28.00  81.00   0.50   45.00    --    1.00  57.00-180.00  218
  3  \w     48.00  82.00   0.50   45.00    --    1.00  57.00 -30.00   68
  4  \w      5.00  89.00   0.50   45.00    --    1.00  38.00 -90.00  168
  5  \w    -31.00  88.00   0.50   45.00    --   -1.30  57.00 150.00  238
  6  \w      2.00  28.00   0.50   45.00    --   -1.30  57.00-120.00   52
;
_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      0.0189946000
_diffrn_orient_matrix_UB_12      0.0410517000
_diffrn_orient_matrix_UB_13      -0.0067932000
_diffrn_orient_matrix_UB_21      0.0425395000
_diffrn_orient_matrix_UB_22      -0.0189948000
_diffrn_orient_matrix_UB_23      -0.0127123000
_diffrn_orient_matrix_UB_31      -0.0354551000
_diffrn_orient_matrix_UB_32      -0.0008339000
_diffrn_orient_matrix_UB_33      -0.0483859000
_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  0.0554
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 0.9969
_diffrn_reflns_Laue_measured_fraction_max 0.9972
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            52554
_diffrn_reflns_point_group_measured_fraction_full 0.9969
_diffrn_reflns_point_group_measured_fraction_max 0.9972
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.89
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    5.818
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.321
_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    1.900
_exptl_crystal_description       pinnacoid
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.3030
_refine_diff_density_min         -0.7358
_refine_diff_density_rms         0.0974
_refine_ls_d_res_high            0.8100
_refine_ls_d_res_low             7.0507
_refine_ls_goodness_of_fit_ref   1.0836
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    41
_refine_ls_number_parameters     500
_refine_ls_number_reflns         5603
_refine_ls_number_restraints     260
_refine_ls_restrained_S_all      1.0570
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0372
_refine_ls_shift/su_max          -0.0009
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0261P)^2^+5.7477P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.0961
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -15
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              -9
_reflns_number_gt                4568
_reflns_number_total             5603
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d2cc05539b2.cif
_cod_data_source_block           B14572
_cod_original_sg_symbol_Hall     '-P 2yn '
_cod_database_code               7130985
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C5-C20 \\sim C5-C20B
 with sigma of 0.02
3. Rigid bond restraints
 Br3, C20, C21, C22, C23, C24, C25
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 Br3B, C20B, C21B, C22B, C23B, C24B, C25B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Br3 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25 \\sim Br3B
\\sim C20B \\sim C21B \\sim C22B \\sim C23B \\sim C24B \\sim C25B: within 2A
with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
5. Others
 Sof(Br3B)=Sof(C20B)=Sof(C21B)=Sof(H21B)=Sof(C22B)=Sof(H22B)=Sof(C23B)=
 Sof(H23B)=Sof(C24B)=Sof(C25B)=Sof(H25B)=1-FVAR(1)
 Sof(Br3)=Sof(C20)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(C23)=Sof(H23)=Sof(C24)=
 Sof(H24)=Sof(C25)=Sof(H25)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C11(H11), C12(H12), C15(H15), C17(H17), C18(H18), C19(H19),
 C21(H21), C23(H23), C24(H24), C25(H25), C21B(H21B), C22B(H22B), C23B(H23B),
 C25B(H25B), C28(H28), C30(H30), C31(H31), C32(H32)
;
_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 2.085
_oxdiff_exptl_absorpt_empirical_full_min 0.737