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_7244741
_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         'C12 H16 Cl2 O2 S2'
_chemical_formula_sum            'C12 H16 Cl2 O2 S2'
_chemical_formula_weight         327.26
_chemical_name_systematic
3-butyl-2,4-dichloro-1,5-bis(methylsulfinyl)benzene
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-11
_audit_creation_method
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6380)
;
_audit_update_record
;
2022-01-12 deposited with the CCDC.	2022-03-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.171(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.1703(2)
_cell_length_b                   14.5677(3)
_cell_length_c                   22.8030(5)
_cell_measurement_reflns_used    12279
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      75.9850
_cell_measurement_theta_min      3.6690
_cell_volume                     3007.32(11)
_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 0.999
_diffrn_measured_fraction_theta_max 0.948
_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    105.00 141.00   0.50    0.38    --  105.24  93.00-120.00   72
  2  \w     92.00 123.00   0.50    0.38    --  105.24  15.00-180.00   62
  3  \w    129.00 166.00   0.50    0.38    --  105.24  15.00-180.00   74
  4  \w    -48.00 -20.00   0.50    0.38    --  -91.75  45.00  90.00   56
  5  \w    -51.00 -25.00   0.50    0.38    --  -91.75  45.00  60.00   52
  6  \w    -65.00 -40.00   0.50    0.38    --  -91.75  61.00  30.00   50
  7  \w    -47.00 -22.00   0.50    0.38    --  -91.75  45.00   0.00   50
  8  \w    -48.00 -22.00   0.50    0.38    --  -91.75  45.00 -30.00   52
  9  \w    -11.00  19.00   0.50    0.09    --  -47.20  19.00 -30.00   60
 10  \w    -49.00 -23.00   0.50    0.38    --  -91.75  45.00 -90.00   52
 11  \w    -51.00 -22.00   0.50    0.38    --  -91.75  45.00-180.00   58
 12  \w    -77.00  22.00   0.50    0.09    --  -47.20  93.00-120.00  198
 13  \w    -79.00 -22.00   0.50    0.38    --  -91.75  93.00-120.00  114
 14  \w    -83.00 -23.00   0.50    0.38    --  -91.75 125.00-120.00  120
 15  \w     31.00  75.00   0.50    0.09    --   47.20 -93.00 127.00   88
 16  \w     73.00 103.00   0.50    0.38    --  105.24 -93.00 127.00   60
 17  \w     43.00  68.00   0.50    0.38    --  105.24 -93.00 127.00   50
 18  \w     35.00  63.00   0.50    0.38    --  105.24 -61.00-180.00   56
 19  \w     34.00  77.00   0.50    0.38    --  105.24 -77.00-150.00   86
 20  \w     43.00 104.00   0.50    0.38    --  105.24 -77.00 -60.00  122
 21  \w     35.00  68.00   0.50    0.38    --  105.24 -61.00   0.00   66
 22  \w     38.00  70.00   0.50    0.38    --  105.24 -61.00  30.00   64
 23  \w     34.00  71.00   0.50    0.38    --  105.24 -61.00  60.00   74
 24  \w     37.00  98.00   0.50    0.38    --  105.24 -77.00 150.00  122
 25  \w    -22.00  27.00   0.50    0.09    --   47.20 -19.00  60.00   98
 26  \w   -116.00 -73.00   0.50    0.09    --  -47.20-125.00 -60.00   86
 27  \w   -119.00 -80.00   0.50    0.09    --  -47.20-125.00 -90.00   78
 28  \w   -132.00-106.00   0.50    0.38    --  -91.75 -93.00 127.00   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      0.0625767000
_diffrn_orient_matrix_UB_12      -0.0977946000
_diffrn_orient_matrix_UB_13      -0.0027315000
_diffrn_orient_matrix_UB_21      0.0210052000
_diffrn_orient_matrix_UB_22      -0.0061587000
_diffrn_orient_matrix_UB_23      0.0682989000
_diffrn_orient_matrix_UB_31      -0.1567597000
_diffrn_orient_matrix_UB_32      -0.0398224000
_diffrn_orient_matrix_UB_33      -0.0038039000
_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  0.0630
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            21774
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.396
_diffrn_reflns_theta_min         3.614
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.416
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24265
_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    1.446
_exptl_crystal_description       plate
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.591
_exptl_crystal_size_mid          0.311
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.782
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.139
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         5998
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0695
_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^)+(0.1484P)^2^+1.1653P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1934
_refine_ls_wR_factor_ref         0.2002
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5258
_reflns_number_total             5998
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra00489e2.cif
_cod_data_source_block           exp_1589_auto
_cod_depositor_comments
;

2024-09-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C24 H32 Cl4 O4 S4'
_cod_original_formula_weight         654.53
_cod_original_formula_moiety         '2(C12 H16 Cl2 O2 S2)'
_cod_original_formula_units_Z            4
_cod_database_code               7244741
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C12H16O2S2Cl2
_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:
 C20(H20A,H20B), C8(H8A,H8B), C7(H7A,H7B), C21(H21A,H21B), C9(H9A,H9B),
 C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C13(H13)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C12(H12A,H12B,H12C), C11(H11A,H11B,H11C), C23(H23A,H23B,
 H23C), C10(H10A,H10B,H10C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              28867
_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 2.000
_oxdiff_exptl_absorpt_empirical_full_min 0.431