Synthesis and crystal structure of a sulphur-bridged molecular hoop consisting of 5,7,12,14-tetrathiapentacene
Ueda, Masafumi; Mazaki, Yasuhiro; RSC Advances 12 (2022) 10870–10874; doi:10.1039/D2RA00489E

data_7244740
_publ_section_title
;
 Synthesis and crystal structure of a sulphur-bridged molecular hoop
 consisting of 5,7,12,14-tetrathiapentacene
;
_journal_issue                   18
_journal_name_full               'RSC Advances'
_journal_page_first              10870
_journal_page_last               10874
_journal_paper_doi               10.1039/D2RA00489E
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C22 H16 S5'
_chemical_formula_sum            'C22 H16 S5'
_chemical_formula_weight         440.65
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-18
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6257)
;
_audit_update_record
;
2022-01-12 deposited with the CCDC.	2022-03-28 downloaded from the CCDC.
;
_cell_angle_alpha                93.809(3)
_cell_angle_beta                 104.307(4)
_cell_angle_gamma                118.489(5)
_cell_formula_units_Z            2
_cell_length_a                   10.4234(5)
_cell_length_b                   10.8106(5)
_cell_length_c                   11.3323(3)
_cell_measurement_reflns_used    3559
_cell_measurement_temperature    120
_cell_measurement_theta_max      70.0450
_cell_measurement_theta_min      5.0610
_cell_volume                     1061.75(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      120
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.966
_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    -37.00   6.00   0.50    0.21    --    0.00  48.00  85.00   86
  2  \w     47.00  82.00   0.50    0.21    --    0.00  48.00  85.00   70
  3  \w     85.00 123.00   0.50    0.86    --   55.92  48.00  85.00   76
  4  \w     69.00 176.00   0.50    0.86    --  111.84  48.00  85.00  214
  5  \w    103.00 173.00   0.50    0.86    --  111.84 111.00 -60.00  140
  6  \w    119.00 146.00   0.50    0.86    --  111.84 178.00 -30.00   54
  7  \w     64.00 112.00   0.50    0.86    --  111.84 178.00 -60.00   96
  8  \w     64.00  89.00   0.50    0.86    --  111.84 178.00 -30.00   50
  9  \w      6.00  79.00   0.50    0.86    --   55.92  48.00  85.00  146
 10  \w     26.00  51.00   0.50    0.86    --  111.84 -48.00 -63.00   50
 11  \w     37.00  96.00   0.50    0.86    --  111.84 -91.00 -60.00  118
 12  \w     64.00 106.00   0.50    0.86    --  111.84-111.00   0.00   84
 13  \w     74.00 111.00   0.50    0.86    --   55.92-125.00 -90.00   74
 14  \w     67.00 105.00   0.50    0.86    --  111.84-111.00-180.00   76
 15  \w     41.00  68.00   0.50    0.86    --  111.84 -63.00-120.00   54
 16  \w     30.00  56.00   0.50    0.86    --  111.84 -50.00-150.00   52
 17  \w     15.00  63.00   0.50    0.86    --   55.92 -61.00-120.00   96
 18  \w     60.00 108.00   0.50    0.86    --  111.84-111.00 -60.00   96
 19  \w     44.00  73.00   0.50    0.86    --  111.84 -63.00   0.00   58
 20  \w     30.00  56.00   0.50    0.86    --  111.84-111.00 -60.00   52
 21  \w     27.00  56.00   0.50    0.86    --  111.84 -50.00 -30.00   58
 22  \w     41.00 171.00   0.50    0.86    --  111.84  37.00 -60.00  260
 23  \w     65.00 104.00   0.50    0.86    --  111.84-111.00  90.00   78
 24  \w     70.00  96.00   0.50    0.86    --  111.84-111.00 150.00   52
 25  \w     47.00  87.00   0.50    0.86    --  111.84-111.00 120.00   80
 26  \w     25.00  60.00   0.50    0.86    --  111.84-111.00 150.00   70
 27  \w    -22.00  43.00   0.50    0.86    --   55.92 -48.00 -63.00  130
 28  \w      2.00  39.00   0.50    0.21    --    0.00 -99.00 -90.00   74
 29  \w    -29.00   5.00   0.50    0.86    --   55.92 -61.00-120.00   68
 30  \w    -35.00  -9.00   0.50    0.21    --    0.00 -48.00 -63.00   52
 31  \w    -64.00 -27.00   0.50    0.86    --  -55.92 -48.00 -63.00   74
 32  \w    -12.00  20.00   0.50    0.86    --  -55.92  30.00 -90.00   64
 33  \w    -24.00  27.00   0.50    0.86    --  -55.92  15.00-120.00  102
 34  \w    -48.00 -23.00   0.50    0.86    -- -106.00  50.00-120.00   50
 35  \w    -78.00 -13.00   0.50    0.86    --  -55.92 125.00-150.00  130
 36  \w    -72.00 -43.00   0.50    0.86    -- -106.00 178.00 -30.00   58
 37  \w    -86.00 -40.00   0.50    0.86    --  -55.92 125.00  60.00   92
 38  \w    -49.00  27.00   0.50    0.86    --  -55.92  48.00  85.00  152
 39  \w    -54.00 -28.00   0.50    0.86    -- -106.00  48.00  85.00   52
 40  \w    -70.00 -23.00   0.50    0.86    -- -106.00 111.00  90.00   94
 41  \w    -67.00 -42.00   0.50    0.86    -- -106.00 178.00  60.00   50
 42  \w   -112.00 -74.00   0.50    0.86    -- -106.00 178.00  60.00   76
 43  \w   -114.00 -77.00   0.50    0.86    -- -106.00 178.00 -30.00   74
 44  \w   -118.00 -43.00   0.50    0.86    -- -106.00 178.00 -90.00  150
 45  \w   -119.00 -79.00   0.50    0.86    --  -55.92 -48.00 -63.00   80
 46  \w    -91.00 -63.00   0.50    0.86    -- -106.00 -48.00 -63.00   56
 47  \w   -128.00 -74.00   0.50    0.86    --  -55.92-125.00  60.00  108
 48  \w   -116.00 -87.00   0.50    0.86    -- -106.00-111.00  90.00   58
 49  \w   -143.00 -73.00   0.50    0.86    --  -55.92-125.00  30.00  140
 50  \w      1.00  27.00   0.50    0.21    --    0.00 -99.00  60.00   52
 51  \w   -133.00 -85.00   0.50    0.86    -- -106.00-111.00-120.00   96
 52  \w   -144.00 -83.00   0.50    0.86    --  -55.92 -94.00   0.00  122
 53  \w   -159.00-133.00   0.50    0.86    -- -106.00 -48.00 -63.00   52
 54  \w   -177.00-141.00   0.50    0.86    -- -106.00-111.00-120.00   72
 55  \w   -172.00-147.00   0.50    0.86    -- -106.00-111.00  90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1618715000
_diffrn_orient_matrix_UB_12      0.0428135000
_diffrn_orient_matrix_UB_13      0.0843024000
_diffrn_orient_matrix_UB_21      -0.0606847000
_diffrn_orient_matrix_UB_22      -0.1565410000
_diffrn_orient_matrix_UB_23      0.0160214000
_diffrn_orient_matrix_UB_31      0.0396577000
_diffrn_orient_matrix_UB_32      -0.0352503000
_diffrn_orient_matrix_UB_33      -0.1152656000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8959
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.007
_diffrn_reflns_theta_min         4.124
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.055
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.067
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3960
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0326
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0366P)^2^+0.4889P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0849
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3487
_reflns_number_total             3960
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra00489e2.cif
_cod_data_source_block           exp_1062
_cod_original_cell_volume        1061.75(9)
_cod_database_code               7244740
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C44H32S10
_reflns_odcompleteness_completeness 99.42
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C7(H7), C13(H13), C16(H16), C4(H4), C17(H17), C3(H3)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_shelx_res_checksum              83127
_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 1.292
_oxdiff_exptl_absorpt_empirical_full_min 0.837