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_7244738
_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      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             2021-04-08
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-01-12 deposited with the CCDC.	2022-03-28 downloaded from the CCDC.
;
_cell_angle_alpha                79.588(4)
_cell_angle_beta                 76.006(4)
_cell_angle_gamma                88.447(4)
_cell_formula_units_Z            4
_cell_length_a                   9.4018(4)
_cell_length_b                   9.7068(5)
_cell_length_c                   16.7103(9)
_cell_measurement_reflns_used    6707
_cell_measurement_temperature    120.15
_cell_measurement_theta_max      70.9610
_cell_measurement_theta_min      2.7580
_cell_volume                     1455.16(13)
_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      120.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_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    -24.00   1.00   0.50    0.05    --    0.00 -78.00 112.00   50
  2  \w     17.00  76.00   0.50    0.22    --   55.92 -78.00 112.00  118
  3  \w     66.00 102.00   0.50    0.22    --  111.84 -78.00 112.00   72
  4  \w     61.00 108.00   0.50    0.22    --  111.84-111.00  90.00   94
  5  \w     40.00 103.00   0.50    0.22    --  111.84 -91.00  90.00  126
  6  \w     36.00 110.00   0.50    0.22    --   55.92-125.00   0.00  148
  7  \w     83.00 108.00   0.50    0.22    --  111.84-111.00 -30.00   50
  8  \w     63.00 104.00   0.50    0.22    --  111.84-111.00-120.00   82
  9  \w     52.00 108.00   0.50    0.22    --  111.84-111.00-150.00  112
 10  \w     27.00  57.00   0.50    0.22    --  111.84 -50.00-180.00   60
 11  \w     30.00  56.00   0.50    0.22    --  111.84 -50.00-120.00   52
 12  \w     25.00  50.00   0.50    0.22    --  111.84-111.00 -30.00   50
 13  \w     24.00 102.00   0.50    0.22    --  111.84-111.00   0.00  156
 14  \w     30.00  56.00   0.50    0.22    --  111.84 -50.00 150.00   52
 15  \w     31.00  57.00   0.50    0.22    --  111.84 -50.00  90.00   52
 16  \w     28.00  55.00   0.50    0.22    --  111.84-111.00  90.00   54
 17  \w     15.00 102.00   0.50    0.22    --  111.84 -91.00   0.00  174
 18  \w    -11.00  35.00   0.50    0.05    --    0.00  78.00-122.00   92
 19  \w    -33.00  25.00   0.50    0.22    --   55.92 -15.00   0.00  116
 20  \w    -16.00  28.00   0.50    0.22    --   55.92 -30.00 -90.00   88
 21  \w     31.00  57.00   0.50    0.05    --    0.00 -99.00 -60.00   52
 22  \w      4.00  29.00   0.50    0.05    --    0.00 -99.00 -60.00   50
 23  \w    -24.00   2.00   0.50    0.22    --  -55.92  15.00 -90.00   52
 24  \w    -48.00   4.00   0.50    0.22    --  -55.92  78.00-122.00  104
 25  \w    -24.00   2.00   0.50    0.22    --  -55.92  15.00-180.00   52
 26  \w    -56.00 -23.00   0.50    0.22    -- -106.00  50.00-120.00   66
 27  \w    -74.00 -23.00   0.50    0.22    -- -106.00  63.00 -60.00  102
 28  \w    -15.00  26.00   0.50    0.22    --  -55.92  15.00  30.00   82
 29  \w     -5.00  26.00   0.50    0.22    --  -55.92  45.00  30.00   62
 30  \w    -24.00  14.00   0.50    0.22    --  -55.92  15.00   0.00   76
 31  \w    -56.00 -24.00   0.50    0.22    -- -106.00  50.00  60.00   64
 32  \w    -65.00 -24.00   0.50    0.22    -- -106.00   0.00 120.00   82
 33  \w    -67.00 -40.00   0.50    0.22    -- -106.00  63.00  60.00   54
 34  \w    -81.00 -26.00   0.50    0.22    --  -55.92 125.00   0.00  110
 35  \w    -70.00 -40.00   0.50    0.05    --    0.00 178.00 -60.00   60
 36  \w    -86.00 -36.00   0.50    0.22    --  -55.92 125.00 -30.00  100
 37  \w    -91.00 -66.00   0.50    0.22    -- -106.00  78.00-122.00   50
 38  \w   -106.00 -27.00   0.50    0.22    -- -106.00 -12.00  30.00  158
 39  \w   -110.00 -84.00   0.50    0.22    -- -106.00   0.00 120.00   52
 40  \w   -114.00 -11.00   0.50    0.22    --  -55.92 -78.00 112.00  206
 41  \w    -91.00 -55.00   0.50    0.05    --    0.00 -78.00 112.00   72
 42  \w    -41.00  11.00   0.50    0.22    --   55.92 -15.00 150.00  104
 43  \w     73.00 176.00   0.50    0.22    --  111.84  63.00 150.00  206
 44  \w    111.00 136.00   0.50    0.22    --  111.84 178.00  30.00   50
 45  \w    148.00 177.00   0.50    0.22    --  111.84  78.00-122.00   58
 46  \w     64.00 135.00   0.50    0.22    --  111.84  78.00-122.00  142
 47  \w      8.00 134.00   0.50    0.22    --   55.92  78.00-122.00  252
 48  \w   -119.00 -92.00   0.50    0.22    -- -106.00-111.00-180.00   54
 49  \w   -176.00-138.00   0.50    0.22    -- -106.00-111.00-180.00   76
 50  \w   -177.00 -83.00   0.50    0.22    -- -106.00 -50.00  30.00  188
 51  \w   -135.00 -68.00   0.50    0.22    -- -106.00 -78.00 112.00  134
 52  \w   -164.00-139.00   0.50    0.22    -- -106.00 -78.00 112.00   50
 53  \w   -171.00-116.00   0.50    0.22    -- -106.00   0.00 120.00  110
 54  \w   -165.00-140.00   0.50    0.22    -- -106.00 -12.00  30.00   50
 55  \w   -119.00 -42.00   0.50    0.22    -- -106.00 178.00 -30.00  154
;
_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      0.0552578000
_diffrn_orient_matrix_UB_12      -0.0249589000
_diffrn_orient_matrix_UB_13      0.0809567000
_diffrn_orient_matrix_UB_21      0.0190770000
_diffrn_orient_matrix_UB_22      0.1592742000
_diffrn_orient_matrix_UB_23      -0.0073357000
_diffrn_orient_matrix_UB_31      -0.1584561000
_diffrn_orient_matrix_UB_32      0.0074798000
_diffrn_orient_matrix_UB_33      0.0521569000
_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  0.0568
_diffrn_reflns_av_unetI/netI     0.0599
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13636
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.108
_diffrn_reflns_theta_min         2.770
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.629
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35959
_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    1.494
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.386
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.636
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         5453
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0641P)^2^+0.5507P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1237
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5164
_reflns_number_total             5453
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra00489e2.cif
_cod_data_source_block           exp_1080
_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            2
_cod_database_code               7244738
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C12H16O2S2Cl2
_shelx_estimated_absorpt_t_max   0.654
_shelx_estimated_absorpt_t_min   0.184
_reflns_odcompleteness_completeness 99.90
_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:
 C8B(H8BA,H8BB), C7B(H7BA,H7BB), C9B(H9BA,H9BB), C7A(H7AA,H7AB), C8A(H8AA,
 H8AB), C9A(H9AA,H9AB)
2.b Aromatic/amide H refined with riding coordinates:
 C6A(H6A), C6B(H6B)
2.c Idealised Me refined as rotating group:
 C12B(H12A,H12B,H12C), C12A(H12D,H12E,H12F), C11B(H11A,H11B,H11C), C10B(H10A,
 H10B,H10C), C10A(H10D,H10E,H10F), C11A(H11D,H11E,H11F)
;
_shelx_res_checksum              30968
_olex2_submission_original_sample_id
3-butyl-2,4-dichloro-1,5-bis(methylsulfinyl)benzene
_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 2.438
_oxdiff_exptl_absorpt_empirical_full_min 0.529