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_7130984
_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         'C11 H11 O S2, C6 H13 N2'
_chemical_formula_sum            'C17 H24 N2 O S2'
_chemical_formula_weight         336.50
_chemical_name_systematic
;
'1,4-diazabicyclo[2.2.2]octan-1-ium 2-(4-isopropylphenyl)-2-oxoethanedithioate'
;
_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   mixed
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-08-09
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-08-09 deposited with the CCDC.	2022-11-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.827(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.9171(10)
_cell_length_b                   11.5193(10)
_cell_length_c                   10.7037(8)
_cell_measurement_reflns_used    7425
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.8040
_cell_measurement_theta_min      2.3300
_cell_volume                     1817.5(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_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   30.00    --    1.00  57.00 -60.00  236
  2  \w    -30.00  90.00   0.50   30.00    --    1.00  38.00-180.00  240
  3  \w     44.00  90.00   0.50   30.00    --    1.00  38.00-180.00   92
  4  \w    -30.00   3.00   0.50   30.00    --    1.00  38.00-180.00   66
  5  \w     -3.00  86.00   0.50   30.00    --   -1.30  57.00-120.00  178
  6  \w     42.00  82.00   0.50   30.00    --   -1.30  38.00 150.00   80
;
_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      0.0114851000
_diffrn_orient_matrix_UB_12      0.0445454000
_diffrn_orient_matrix_UB_13      -0.0404950000
_diffrn_orient_matrix_UB_21      0.0467301000
_diffrn_orient_matrix_UB_22      -0.0113474000
_diffrn_orient_matrix_UB_23      0.0200726000
_diffrn_orient_matrix_UB_31      -0.0004439000
_diffrn_orient_matrix_UB_32      -0.0410109000
_diffrn_orient_matrix_UB_33      -0.0494819000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7441
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.732
_diffrn_reflns_theta_min         2.244
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.943
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.64a (Rigaku Oxford Diffraction, 2022)
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    1.230
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.287
_exptl_crystal_size_mid          0.225
_exptl_crystal_size_min          0.022
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         7441
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0415
_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^)+(0.0695P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1173
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5260
_reflns_number_total             7441
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 179.9816\% 
around [-0.21 0.00 0.98] (reciprocal) or [0.00 -0.00 1.00] (direct)
;
_cod_data_source_file            d2cc05539b2.cif
_cod_data_source_block           B14515_twin_hklf5
_cod_database_code               7130984
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.6281(11)
 0.3719(11)
2. 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
3. Restrained distances
 S1-C1 \\sim S1A-C1
 with sigma of 0.02
 S2-C1 \\sim S2A-C1
 with sigma of 0.02
 O1-C2 \\sim O1A-C2
 with sigma of 0.02
4. Others
 Sof(S1A)=Sof(S2A)=Sof(O1A)=1-FVAR(1)
 Sof(S1)=Sof(S2)=Sof(O1)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C9(H9)
5.b Secondary CH2 refined with riding coordinates:
 C5'(H5'A,H5'B), C6'(H6'A,H6'B), C1'(H1'A,H1'B), C7'(H7'A,H7'B), C2'(H2'A,
 H2'B), C4'(H4'A,H4'B)
5.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C7(H7), C4(H4), C5(H5)
5.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_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 1.452
_oxdiff_exptl_absorpt_empirical_full_min 0.490
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2