Extension of the π-conjugated core of methylchalcogenolated polycyclic aromatic hydrocarbons: synthesis and characterization of 1,4,7,10-tetrakis(methylthio)- and tetramethoxy-coronene.
Pal, Prasanta; Bulgarevich, Kirill; Hanaki, Ryota; Kawabata, Kohsuke; Takimiya, Kazuo; Chemical science 16 (2025) 15368–15377; doi:10.1039/d5sc03215f

data_1575292
_publ_section_title
;
 Extension of the &#x3c0;-conjugated core of methylchalcogenolated
 polycyclic aromatic hydrocarbons: synthesis and characterization of
 1,4,7,10-tetrakis(methylthio)- and tetramethoxy-coronene.
;
_journal_issue                   34
_journal_name_full               'Chemical science'
_journal_page_first              15368
_journal_page_last               15377
_journal_paper_doi               10.1039/d5sc03215f
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C26 H20 S4'
_chemical_formula_sum            'C26 H20 S4'
_chemical_formula_weight         460.66
_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             2025-02-20
_audit_creation_method
;
Olex2 1.5-ac7-013
(compiled 2025.01.02 svn.rf662f148 for Rigaku Oxford Diffraction, GUI svn.r7109)
;
_audit_update_record
;
2025-04-25 deposited with the CCDC.	2025-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                89.4690(10)
_cell_angle_beta                 77.308(2)
_cell_angle_gamma                87.6390(10)
_cell_formula_units_Z            1
_cell_length_a                   5.09140(10)
_cell_length_b                   9.07180(10)
_cell_length_c                   11.3386(2)
_cell_measurement_reflns_used    14965
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      75.6860
_cell_measurement_theta_min      3.9380
_cell_volume                     510.479(15)
_computing_cell_refinement       'CrysAlisPro 1.171.44.94a (Rigaku OD, 2025)'
_computing_data_collection       'CrysAlisPro 1.171.44.94a (Rigaku OD, 2025)'
_computing_data_reduction        'CrysAlisPro 1.171.44.94a (Rigaku OD, 2025)'
_computing_molecular_graphics    'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      200(2)
_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 0.937
_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    -65.00 -26.00   0.50    0.05    --  -97.00  57.00-180.00   78
  2  \w    -72.00 -36.00   0.50    0.05    --  -97.00 125.00 -90.00   72
  3  \w   -108.00 -80.00   0.50    0.05    --  -97.00 125.00 -90.00   56
  4  \w    -58.00 -27.00   0.50    0.05    --  -97.00  57.00 -60.00   62
  5  \w    -69.00  24.00   0.50    0.05    --  -48.04  77.00  60.00  186
  6  \w     27.00 119.00   0.50    0.05    --   48.04  77.00 150.00  184
  7  \w     35.00 119.00   0.50    0.05    --   48.04  57.00  30.00  168
  8  \w     27.00 119.00   0.50    0.05    --   48.04  77.00 -30.00  184
  9  \w     27.00 119.00   0.50    0.05    --   48.04  77.00 -90.00  184
 10  \w     27.00 119.00   0.50    0.05    --   48.04  77.00-150.00  184
 11  \w     35.00 119.00   0.50    0.05    --   48.04  57.00-180.00  168
 12  \w     40.00 120.00   0.50    0.05    --   48.04  37.00  30.00  160
 13  \w     31.00 124.00   0.50    0.05    --   52.00  78.00  79.00  186
 14  \w     33.00 124.00   0.50    0.05    --   52.00  74.00 127.98  182
 15  \w     35.00 128.00   0.50    0.05    --   56.00  77.00  57.81  186
 16  \w     39.00 131.00   0.50    0.05    --   60.00  77.00  32.08  184
 17  \w     44.00 136.00   0.50    0.05    --   64.00  75.00  27.61  184
 18  \w     48.00 139.00   0.50    0.05    --   68.00  75.00-172.87  182
 19  \w     42.00 131.00   0.50    0.05    --   60.00  71.00 177.21  178
 20  \w      0.00  27.00   0.50    0.05    --   28.00  93.00  51.84   54
 21  \w     35.00  91.00   0.50    0.05    --  104.77 -77.00 -90.00  112
 22  \w     36.00 101.00   0.50    0.05    --  104.77 -77.00  90.00  130
 23  \w     34.00  62.00   0.50    0.05    --  104.77 -57.00 150.00   56
 24  \w     37.00  72.00   0.50    0.05    --  104.77 -99.00  90.00   70
 25  \w     66.00 106.00   0.50    0.05    --  104.77 -99.00  30.00   80
 26  \w     17.00  92.00   0.50    0.05    --   48.04-125.00   0.00  150
 27  \w     42.00  70.00   0.50    0.05    --  104.77-125.00 -90.00   56
 28  \w     39.00  99.00   0.50    0.05    --  104.77-125.00-120.00  120
 29  \w     79.00 105.00   0.50    0.05    --  104.77-125.00 -90.00   52
 30  \w     36.00  80.00   0.50    0.05    --  104.77 -99.00   0.00   88
 31  \w     36.00  62.00   0.50    0.05    --  104.77 -99.00  30.00   52
 32  \w     51.00 101.00   0.50    0.05    --  104.77 -99.00  60.00  100
 33  \w     81.00 106.00   0.50    0.05    --  104.77 -99.00  90.00   50
 34  \w   -119.00 -27.00   0.50    0.05    --  -48.04 -77.00 -60.00  184
 35  \w   -119.00 -27.00   0.50    0.05    --  -48.04 -77.00-120.00  184
 36  \w   -119.00 -35.00   0.50    0.05    --  -48.04 -57.00-180.00  168
 37  \w   -120.00 -41.00   0.50    0.05    --  -48.04 -19.00-150.00  158
 38  \w   -119.00 -35.00   0.50    0.05    --  -48.04 -57.00 -90.00  168
 39  \w   -119.00 -35.00   0.50    0.05    --  -48.04 -57.00 -30.00  168
 40  \w   -120.00 -40.00   0.50    0.05    --  -48.04 -26.00   0.13  160
 41  \w   -119.00 -35.00   0.50    0.05    --  -48.04 -57.00  60.00  168
 42  \w   -120.00 -41.00   0.50    0.05    --  -48.04 -19.00 120.00  158
 43  \w   -160.00 -77.00   0.50    0.05    --  -88.00 -51.00 155.95  166
 44  \w   -169.00 -76.00   0.50    0.05    --  -97.00 -77.00  90.00  186
 45  \w   -169.00 -76.00   0.50    0.05    --  -97.00 -77.00  90.00  186
 46  \w   -125.00 -77.00   0.50    0.05    --  -97.00 -77.00   0.00   96
 47  \w   -111.00 -80.00   0.50    0.05    --  -97.00 -74.00 -68.79   62
 48  \w   -117.00 -80.00   0.50    0.05    --  -97.00 -76.00-107.63   74
 49  \w   -165.00-125.00   0.50    0.05    --  -97.00 -76.00-107.63   80
 50  \w   -156.00 -82.00   0.50    0.05    --  -97.00 -77.00-150.00  148
 51  \w   -162.00-117.00   0.50    0.05    --  -97.00 -74.00 -68.79   90
 52  \w   -164.00 -76.00   0.50    0.05    --  -92.00 -66.00-100.82  176
 53  \w   -144.00 -55.00   0.50    0.05    --  -72.00 -69.00 -17.60  178
 54  \w   -164.00 -76.00   0.50    0.05    --  -92.00 -66.00-100.82  176
 55  \w   -156.00 -66.00   0.50    0.05    --  -84.00 -71.00  -0.94  180
 56  \w   -156.00 -68.00   0.50    0.05    --  -84.00 -65.00   1.41  176
 57  \w   -156.00 -68.00   0.50    0.05    --  -84.00 -65.00   1.41  176
 58  \w   -139.00 -53.00   0.50    0.05    --  -68.00 -63.00  38.72  172
 59  \w   -139.00 -52.00   0.50    0.05    --  -68.00 -66.00 109.06  174
 60  \w   -156.00 -68.00   0.50    0.05    --  -84.00 -64.00 133.13  176
 61  \w   -128.00 -79.00   0.50    0.05    --  -97.00 -71.00 149.43   98
 62  \w   -139.00 -52.00   0.50    0.05    --  -68.00 -66.00 109.06  174
 63  \w   -136.00 -49.00   0.50    0.05    --  -64.00 -63.00  77.52  174
 64  \w   -148.00 -61.00   0.50    0.05    --  -76.00 -62.00   7.46  174
 65  \w   -160.00 -73.00   0.50    0.05    --  -88.00 -62.00 -75.48  174
 66  \w   -160.00 -73.00   0.50    0.05    --  -88.00 -62.00 -75.48  174
 67  \w   -139.00 -53.00   0.50    0.05    --  -68.00 -62.00-102.60  172
 68  \w   -144.00 -58.00   0.50    0.05    --  -72.00 -61.00 -90.89  172
 69  \w   -152.00 -66.00   0.50    0.05    --  -80.00 -61.00 -91.91  172
 70  \w   -139.00 -54.00   0.50    0.05    --  -68.00 -60.00 -75.68  170
 71  \w   -139.00 -53.00   0.50    0.05    --  -68.00 -63.00-114.72  172
 72  \w   -139.00 -53.00   0.50    0.05    --  -68.00 -63.00-126.81  172
 73  \w   -139.00 -53.00   0.50    0.05    --  -68.00 -62.00-137.38  172
 74  \w   -144.00 -58.00   0.50    0.05    --  -72.00 -61.00-146.08  172
 75  \w   -139.00 -54.00   0.50    0.05    --  -68.00 -60.00 -75.68  170
 76  \w   -144.00 -58.00   0.50    0.05    --  -72.00 -60.00 -80.68  172
 77  \w   -122.00 -87.00   0.50    0.05    --  -97.00 -59.00 -34.25   70
 78  \w   -153.00-125.00   0.50    0.05    --  -97.00 -59.00 -34.25   56
 79  \w   -156.00 -70.00   0.50    0.05    --  -84.00 -59.00 -63.67  172
 80  \w   -144.00 -58.00   0.50    0.05    --  -72.00 -60.00  22.71  172
 81  \w   -156.00 -70.00   0.50    0.05    --  -84.00 -59.00  25.51  172
 82  \w   -160.00 -74.00   0.50    0.05    --  -88.00 -59.00 113.32  172
 83  \w   -160.00 -74.00   0.50    0.05    --  -88.00 -59.00 113.32  172
 84  \w   -168.00 -83.00   0.50    0.05    --  -96.00 -58.00 102.77  170
 85  \w   -152.00 -67.00   0.50    0.05    --  -80.00 -58.00  94.79  170
 86  \w   -120.00 -88.00   0.50    0.05    --  -97.00 -58.00  56.77   64
 87  \w   -154.00-129.00   0.50    0.05    --  -97.00 -58.00  56.77   50
 88  \w   -168.00 -83.00   0.50    0.05    --  -96.00 -58.00 102.77  170
 89  \w   -148.00 -63.00   0.50    0.05    --  -76.00 -58.00  62.44  170
 90  \w   -144.00 -59.00   0.50    0.05    --  -72.00 -58.00 178.68  170
 91  \w   -144.00 -59.00   0.50    0.05    --  -72.00 -58.00 178.68  170
 92  \w   -148.00 -90.00   0.50    0.05    --  -97.00 -60.00  29.94  116
 93  \w   -158.00 -86.00   0.50    0.05    --  -97.00 -57.00  16.59  144
 94  \w   -144.00 -59.00   0.50    0.05    --  -72.00 -58.00 -65.98  170
 95  \w   -148.00 -62.00   0.50    0.05    --  -76.00 -59.00-156.94  172
 96  \w   -148.00 -63.00   0.50    0.05    --  -76.00 -58.00-168.48  170
 97  \w   -156.00 -71.00   0.50    0.05    --  -84.00 -56.00-174.41  170
 98  \w   -156.00 -71.00   0.50    0.05    --  -84.00 -56.00-174.41  170
 99  \w   -160.00 -76.00   0.50    0.05    --  -88.00 -55.00  77.21  168
100  \w   -160.00 -77.00   0.50    0.05    --  -88.00 -51.00 155.95  166
101  \w   -166.00 -82.00   0.50    0.05    --  -97.00-125.00   0.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, SynergyCustom DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0642227000
_diffrn_orient_matrix_UB_12      0.0018631000
_diffrn_orient_matrix_UB_13      0.1392498000
_diffrn_orient_matrix_UB_21      0.0845268000
_diffrn_orient_matrix_UB_22      -0.1649468000
_diffrn_orient_matrix_UB_23      0.0010621000
_diffrn_orient_matrix_UB_31      0.2916954000
_diffrn_orient_matrix_UB_32      0.0409481000
_diffrn_orient_matrix_UB_33      -0.0021831000
_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  0.0671
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            29297
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.257
_diffrn_reflns_theta_min         3.996
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.355
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.44.94a (Rigaku Oxford Diffraction, 2025)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_description       plate
_exptl_crystal_F_000             240
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.228
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2035
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.228
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0808
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0343P)^2^+3.4579P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2223
_refine_ls_wR_factor_ref         0.2241
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1803
_reflns_number_total             2035
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc03215f2.cif
_cod_data_source_block           250220_mt-benzoperylene_plate_200k_auto
_cod_depositor_comments
'Adding full bibliography for 1575279--1575293.cif.'
_cod_database_code               1575292
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHS
_chemical_oxdiff_usercomment     ' '
_diffrn_oxdiff_digest_hkl
;
4348c4eb7556bc06169b09688d97d90ecf2277
;
_diffrn_oxdiff_digest_od_ed
;

;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H003(0.5) H005(0.5) C00F(0.5) H00H(0.5) C00G(0.5) H00I(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C003(H003), C005(H005), C007(H007), C00B(H00B), C00F(H00H), C00G(H00I)
3.b Idealised Me refined as rotating group:
 C00D(H00A,H00C,H00D), C00E(H00E,H00F,H00G)
;
_shelx_res_checksum              92781
_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 1.823
_oxdiff_exptl_absorpt_empirical_full_min 0.646