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_7244742
_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, C6 H6'
_chemical_formula_sum            'C28 H22 S5'
_chemical_formula_weight         518.75
_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             2022-02-16
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-02-21 deposited with the CCDC.	2022-03-28 downloaded from the CCDC.
;
_cell_angle_alpha                76.325(2)
_cell_angle_beta                 78.743(2)
_cell_angle_gamma                88.930(2)
_cell_formula_units_Z            1
_cell_length_a                   9.6067(3)
_cell_length_b                   11.3115(2)
_cell_length_c                   11.6687(2)
_cell_measurement_reflns_used    6457
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      70.8950
_cell_measurement_theta_min      3.9760
_cell_volume                     1207.84(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.116a (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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.963
_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      2.00  33.00   0.50    0.05    --    0.00  72.00-132.00   62
  2  \w     43.00  81.00   0.50    0.05    --    0.00  72.00-132.00   76
  3  \w     11.00 132.00   0.50    0.05    --   55.92  72.00-132.00  242
  4  \w     66.00 177.00   0.50    0.05    --  111.84  72.00-132.00  222
  5  \w     76.00 178.00   0.50    0.05    --  111.84   0.00-150.00  204
  6  \w     13.00  66.00   0.50    0.05    --  111.84   0.00-150.00  106
  7  \w      2.00  47.00   0.50    0.05    --    0.00 -99.00-150.00   90
  8  \w     36.00 104.00   0.50    0.05    --   55.92-125.00 -60.00  136
  9  \w     71.00 108.00   0.50    0.05    --  111.84-111.00 -90.00   74
 10  \w     60.00 108.00   0.50    0.05    --  111.84-111.00-180.00   96
 11  \w     77.00 108.00   0.50    0.05    --  111.84-111.00   0.00   62
 12  \w     34.00  93.00   0.50    0.05    --   55.92-125.00 120.00  118
 13  \w     75.00 107.00   0.50    0.05    --  111.84-111.00  90.00   64
 14  \w     38.00 101.00   0.50    0.05    --  111.84-111.00 150.00  126
 15  \w     24.00  65.00   0.50    0.05    --  111.84-111.00  90.00   82
 16  \w     37.00  63.00   0.50    0.05    --  111.84-111.00   0.00   52
 17  \w     35.00  61.00   0.50    0.05    --  111.84-111.00-120.00   52
 18  \w     27.00  53.00   0.50    0.05    --  111.84-111.00-180.00   52
 19  \w     19.00  44.00   0.50    0.05    --    0.00 -99.00 -60.00   50
 20  \w    -42.00  17.00   0.50    0.05    --   55.92 -15.00 -30.00  118
 21  \w    -17.00   9.00   0.50    0.05    --    0.00 -72.00  96.00   52
 22  \w     20.00  45.00   0.50    0.05    --    0.00 -72.00  96.00   50
 23  \w     33.00  90.00   0.50    0.05    --   55.92 -72.00  96.00  114
 24  \w     43.00  72.00   0.50    0.05    --  111.84 -63.00 150.00   58
 25  \w     57.00  83.00   0.50    0.05    --  111.84 -72.00  96.00   52
 26  \w     32.00  57.00   0.50    0.05    --  111.84 -50.00 -90.00   50
 27  \w     28.00  53.00   0.50    0.05    --  111.84 -50.00-120.00   50
 28  \w     27.00  53.00   0.50    0.05    --  111.84 -50.00-180.00   52
 29  \w     49.00  74.00   0.50    0.05    --  111.84 -63.00-150.00   50
 30  \w     31.00  57.00   0.50    0.05    --  111.84 -50.00  90.00   52
 31  \w     27.00  57.00   0.50    0.05    --  111.84 -50.00 120.00   60
 32  \w     27.00  52.00   0.50    0.05    --  111.84 -50.00 150.00   50
 33  \w    -33.00  18.00   0.50    0.05    --   55.92 -15.00 -90.00  102
 34  \w    -79.00 -36.00   0.50    0.05    -- -106.00  72.00-132.00   86
 35  \w    -56.00 -31.00   0.50    0.05    --  -55.92  72.00-132.00   50
 36  \w    -57.00 -32.00   0.50    0.05    -- -106.00  50.00   0.00   50
 37  \w    -53.00 -27.00   0.50    0.05    -- -106.00  50.00  60.00   52
 38  \w     -2.00  27.00   0.50    0.05    --  -55.92  45.00  30.00   58
 39  \w    -51.00 -25.00   0.50    0.05    --  -55.92  45.00  30.00   52
 40  \w    -22.00  18.00   0.50    0.05    --  -55.92  15.00 -30.00   80
 41  \w    -20.00   5.00   0.50    0.05    --  -55.92  15.00 -90.00   50
 42  \w    -13.00  24.00   0.50    0.05    --  -55.92  15.00-150.00   74
 43  \w    -24.00  14.00   0.50    0.05    --  -55.92  15.00-180.00   76
 44  \w    -63.00 -24.00   0.50    0.05    -- -106.00   0.00 -60.00   78
 45  \w   -176.00 -76.00   0.50    0.05    -- -106.00   0.00 -60.00  200
 46  \w    -80.00 -23.00   0.50    0.05    -- -106.00 111.00 -60.00  114
 47  \w    -62.00 -29.00   0.50    0.05    -- -106.00 111.00 -30.00   66
 48  \w    -80.00 -23.00   0.50    0.05    -- -106.00 111.00  30.00  114
 49  \w    -86.00 -25.00   0.50    0.05    --  -55.92 125.00 -90.00  122
 50  \w    -68.00 -23.00   0.50    0.05    -- -106.00 111.00-120.00   90
 51  \w   -127.00 -13.00   0.50    0.05    --  -55.92 -72.00  96.00  228
 52  \w   -112.00 -86.00   0.50    0.05    -- -106.00 -72.00  96.00   52
 53  \w   -155.00-125.00   0.50    0.05    -- -106.00 -72.00  96.00   60
 54  \w   -143.00 -88.00   0.50    0.05    --  -55.92-125.00 -90.00  110
 55  \w     92.00 144.00   0.50    0.05    --  111.84 178.00  30.00  104
 56  \w     63.00  88.00   0.50    0.05    --  111.84 178.00 120.00   50
 57  \w     94.00 142.00   0.50    0.05    --  111.84 178.00 120.00   96
 58  \w    111.00 137.00   0.50    0.05    --  111.84 178.00-180.00   52
;
_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      0.0251294000
_diffrn_orient_matrix_UB_12      -0.1048610000
_diffrn_orient_matrix_UB_13      0.1045391000
_diffrn_orient_matrix_UB_21      0.1614375000
_diffrn_orient_matrix_UB_22      0.0248504000
_diffrn_orient_matrix_UB_23      -0.0398082000
_diffrn_orient_matrix_UB_31      -0.0079743000
_diffrn_orient_matrix_UB_32      0.0897218000
_diffrn_orient_matrix_UB_33      0.0817932000
_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  0.0311
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10752
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.050
_diffrn_reflns_theta_min         3.976
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.534
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.116a (Rigaku Oxford Diffraction, 2021)
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    1.426
_exptl_crystal_description       block
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.534
_exptl_crystal_size_mid          0.164
_exptl_crystal_size_min          0.131
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4499
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0380
_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^)+(0.0399P)^2^+1.0292P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.0942
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4392
_reflns_number_total             4499
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra00489e2.cif
_cod_data_source_block           exp_1694_auto
_cod_database_code               7244742
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C50H38S10
_chemical_oxdiff_usercomment     'phenylene 2mer -100deg'
_shelx_estimated_absorpt_t_max   0.588
_shelx_estimated_absorpt_t_min   0.196
_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), C3(H3), C4(H4), C7(H7), C13(H13), C16(H16), C17(H17), C24(H24),
 C25(H25), C23(H23), C28(H28), C27(H27), C26(H26)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_shelx_res_checksum              41491
_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 1.751
_oxdiff_exptl_absorpt_empirical_full_min 0.604