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_7244739
_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         'C44 H32 S10, 1.038(C7 H8)'
_chemical_formula_sum            'C51.26 H40.3 S10'
_chemical_formula_weight         976.91
_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     dual
_audit_creation_date             2022-02-18
_audit_creation_method
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6380)
;
_audit_update_record
;
2022-02-21 deposited with the CCDC.	2022-03-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.973(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.2924(3)
_cell_length_b                   6.26750(10)
_cell_length_c                   27.5289(7)
_cell_measurement_reflns_used    5353
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      70.8430
_cell_measurement_theta_min      3.3830
_cell_volume                     2258.78(9)
_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 0.998
_diffrn_measured_fraction_theta_max 0.970
_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     41.00  77.00   0.50    0.13    --    0.00  22.00  69.00   72
  2  \w    -16.00  36.00   0.50    0.13    --    0.00  22.00  69.00  104
  3  \w    -23.00 129.00   0.50    0.50    --   55.92  22.00  69.00  304
  4  \w     38.00 173.00   0.50    0.50    --  111.84  22.00  69.00  270
  5  \w     12.00  39.00   0.50    0.13    --    0.00 -99.00-180.00   54
  6  \w    -57.00 -25.00   0.50    0.50    -- -106.00  50.00-180.00   64
  7  \w    -53.00 -23.00   0.50    0.50    -- -106.00  50.00-120.00   60
  8  \w    -54.00 -23.00   0.50    0.50    -- -106.00  50.00 -90.00   62
  9  \w    -54.00 -28.00   0.50    0.50    -- -106.00  50.00 -60.00   52
 10  \w    -73.00 -26.00   0.50    0.50    -- -106.00  63.00 150.00   94
 11  \w    -53.00 -24.00   0.50    0.50    -- -106.00  50.00 150.00   58
 12  \w    -77.00 -23.00   0.50    0.50    --  -55.92 125.00  60.00  108
 13  \w    -86.00 -20.00   0.50    0.50    --  -55.92 125.00 150.00  132
 14  \w    -59.00 -33.00   0.50    0.50    --  -55.92 125.00  90.00   52
 15  \w   -121.00 -48.00   0.50    0.50    -- -106.00 -22.00 -96.00  146
 16  \w    -39.00  -8.00   0.50    0.50    --   55.92 -22.00 -96.00   62
 17  \w     45.00  70.00   0.50    0.50    --  111.84 -63.00-150.00   50
 18  \w     28.00  53.00   0.50    0.50    --  111.84 -50.00 -90.00   50
 19  \w     27.00  52.00   0.50    0.50    --  111.84 -50.00 -60.00   50
 20  \w     27.00  54.00   0.50    0.50    --  111.84 -50.00  30.00   54
 21  \w     33.00  71.00   0.50    0.50    --  111.84 -63.00 150.00   76
 22  \w    -32.00  27.00   0.50    0.50    --   55.92 -30.00 150.00  118
 23  \w    -76.00  -8.00   0.50    0.13    --    0.00 -22.00 -96.00  136
 24  \w    109.00 139.00   0.50    0.50    --  111.84 111.00 -60.00   60
 25  \w    150.00 177.00   0.50    0.50    --  111.84 111.00 -60.00   54
 26  \w    117.00 146.00   0.50    0.50    --  111.84 178.00 -90.00   58
 27  \w     68.00 116.00   0.50    0.50    --  111.84 178.00 -60.00   96
 28  \w     68.00 108.00   0.50    0.50    --  111.84 178.00 -90.00   80
 29  \w    120.00 145.00   0.50    0.50    --  111.84 178.00-150.00   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      0.1089741000
_diffrn_orient_matrix_UB_12      0.0689797000
_diffrn_orient_matrix_UB_13      -0.0049748000
_diffrn_orient_matrix_UB_21      0.0329839000
_diffrn_orient_matrix_UB_22      -0.0161283000
_diffrn_orient_matrix_UB_23      0.0563285000
_diffrn_orient_matrix_UB_31      0.0297737000
_diffrn_orient_matrix_UB_32      -0.2354614000
_diffrn_orient_matrix_UB_33      -0.0053087000
_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  0.0278
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            9764
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.954
_diffrn_reflns_theta_min         3.260
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.811
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62700
_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    1.436
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.576
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.042
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4234
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0332
_refine_ls_shift/su_max          8.528
_refine_ls_shift/su_mean         0.028
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0418P)^2^+1.2090P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0883
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3786
_reflns_number_total             4234
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra00489e2.cif
_cod_data_source_block           exp_1702_auto
_cod_original_formula_sum        'C51.26 H40.30 S10'
_cod_database_code               7244739
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C58H48S10
_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. Others
 Sof(C29)=Sof(C23)=Sof(C28)=Sof(C27)=Sof(C26)=Sof(C25)=Sof(C24)=Sof(H29A)=
 Sof(H29B)=Sof(H29C)=Sof(H28)=Sof(H27)=Sof(H26)=Sof(H25)=Sof(H24)=FVAR(1)
3.a Free rotating group:
 C29(C23,C28,C27,C26,C25,C24,H29A,H29B,H29C,H28,H27,H26,H25,H24)
3.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C19(H19A,H19B), C21(H21A,H21B)
3.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C16(H16), C4(H4), C13(H13), C17(H17), C3(H3), C1(H1)
3.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_shelx_res_checksum              42936
_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 1.298
_oxdiff_exptl_absorpt_empirical_full_min 0.509