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_1575284
_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             2025-02-21
_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                89.639(2)
_cell_angle_beta                 77.413(2)
_cell_angle_gamma                87.3650(10)
_cell_formula_units_Z            1
_cell_length_a                   5.10100(10)
_cell_length_b                   9.13620(10)
_cell_length_c                   11.3735(2)
_cell_measurement_reflns_used    27264
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      75.8620
_cell_measurement_theta_min      3.9650
_cell_volume                     516.758(15)
_computing_cell_refinement       'CrysAlisPro 1.171.44.94a (Rigaku OD, 2025)'
_computing_data_collection
'CrysAlisPro system (CCD 44.94a 64-bit (release 17-02-2025))'
_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  (Sheldrick, 2015)'
_diffrn_ambient_temperature      300(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.942
_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     -1.00  27.00   0.50    1.20    --   28.00  94.00  69.78   56
  2  \w    -91.00 -23.00   0.50    1.20    --  -48.16 125.00 120.00  136
  3  \w   -119.00 -35.00   0.50    1.20    --  -48.16 -57.00 -90.00  168
  4  \w   -120.00 -40.00   0.50    1.20    --  -48.16 -26.00  16.25  160
  5  \w   -119.00 -27.00   0.50    1.20    --  -48.16 -77.00-180.00  184
  6  \w   -119.00 -27.00   0.50    1.20    --  -48.16 -77.00 -90.00  184
  7  \w   -119.00 -27.00   0.50    1.20    --  -48.16 -77.00-120.00  184
  8  \w   -119.00 -35.00   0.50    1.20    --  -48.16 -57.00 -30.00  168
  9  \w   -119.00 -35.00   0.50    1.20    --  -48.16 -57.00  90.00  168
 10  \w   -119.00 -35.00   0.50    1.20    --  -48.16 -57.00   0.00  168
 11  \w    -23.00  96.00   0.50    1.20    --   48.16   0.00  90.00  238
 12  \w     36.00 119.00   0.50    1.20    --   48.16  57.00  30.00  166
 13  \w     17.00  92.00   0.50    1.20    --   48.16-125.00-180.00  150
 14  \w     41.00 120.00   0.50    1.20    --   48.16  37.00-180.00  158
 15  \w    -23.00  96.00   0.50    1.20    --   48.16   0.00  90.00  238
 16  \w     36.00 119.00   0.50    1.20    --   48.16  57.00-180.00  166
 17  \w     41.00 120.00   0.50    1.20    --   48.16  37.00-180.00  158
 18  \w     28.00 119.00   0.50    1.20    --   48.16  77.00 -30.00  182
 19  \w     41.00 120.00   0.50    1.20    --   48.16  37.00  60.00  158
 20  \w     33.00 124.00   0.50    1.20    --   52.00  74.00 131.36  182
 21  \w     31.00 124.00   0.50    1.20    --   52.00  78.00  82.32  186
 22  \w     31.00 124.00   0.50    1.20    --   52.00  78.00  82.32  186
 23  \w     38.00 128.00   0.50    1.20    --   56.00  72.00  64.27  180
 24  \w     39.00 131.00   0.50    1.20    --   60.00  78.00  34.40  184
 25  \w   -136.00 -48.00   0.50    1.20    --  -64.00 -64.00  79.79  176
 26  \w     44.00 136.00   0.50    1.20    --   64.00  76.00-166.48  184
 27  \w   -139.00 -53.00   0.50    1.20    --  -68.00 -63.00-115.12  172
 28  \w   -139.00 -52.00   0.50    1.20    --  -68.00 -65.00 110.66  174
 29  \w   -139.00 -53.00   0.50    1.20    --  -68.00 -63.00  41.19  172
 30  \w   -139.00 -54.00   0.50    1.20    --  -68.00 -61.00-102.87  170
 31  \w   -139.00 -53.00   0.50    1.20    --  -68.00 -63.00-127.37  172
 32  \w   -144.00 -58.00   0.50    1.20    --  -72.00 -61.00-146.67  172
 33  \w   -144.00 -59.00   0.50    1.20    --  -72.00 -58.00 -65.96  170
 34  \w   -144.00 -55.00   0.50    1.20    --  -72.00 -69.00 -16.43  178
 35  \w   -148.00 -62.00   0.50    1.20    --  -76.00 -61.00 -84.22  172
 36  \w   -148.00 -62.00   0.50    1.20    --  -76.00 -59.00-157.64  172
 37  \w   -148.00 -62.00   0.50    1.20    --  -76.00 -61.00-131.13  172
 38  \w   -148.00 -60.00   0.50    1.20    --  -76.00 -66.00 136.87  176
 39  \w   -148.00 -63.00   0.50    1.20    --  -76.00 -58.00  64.62  170
 40  \w   -148.00 -63.00   0.50    1.20    --  -76.00 -56.00-174.46  170
 41  \w   -148.00 -61.00   0.50    1.20    --  -76.00 -63.00   8.93  174
 42  \w   -152.00 -66.00   0.50    4.00    --  -80.00 -60.00  31.59  172
 43  \w   -152.00 -65.00   0.50    4.00    --  -80.00 -62.00-138.05  174
 44  \w   -152.00 -67.00   0.50    4.00    --  -80.00 -58.00  47.66  170
 45  \w   -152.00 -66.00   0.50    4.00    --  -80.00 -60.00 -73.52  172
 46  \w   -156.00 -70.00   0.50    4.00    --  -84.00 -60.00 119.53  172
 47  \w   -156.00 -64.00   0.50    4.00    --  -84.00 -75.00 -11.35  184
 48  \w   -156.00 -71.00   0.50    4.00    --  -84.00 -57.00 106.46  170
 49  \w   -156.00 -65.00   0.50    4.00    --  -84.00 -72.00  -0.02  182
 50  \w   -156.00 -68.00   0.50    4.00    --  -84.00 -65.00   2.43  176
 51  \w   -156.00 -70.00   0.50    4.00    --  -84.00 -60.00-145.57  172
 52  \w   -156.00 -70.00   0.50    4.00    --  -84.00 -60.00-145.57  172
 53  \w   -156.00 -70.00   0.50    4.00    --  -84.00 -60.00  26.78  172
 54  \w   -156.00 -70.00   0.50    4.00    --  -84.00 -60.00 119.53  172
 55  \w   -156.00 -70.00   0.50    4.00    --  -84.00 -60.00 -63.83  172
 56  \w   -160.00 -69.00   0.50    4.00    --  -88.00 -73.00 168.42  182
 57  \w   -160.00 -69.00   0.50    4.00    --  -88.00 -73.00 168.42  182
 58  \w   -160.00 -73.00   0.50    4.00    --  -88.00 -62.00 -75.77  174
 59  \w   -160.00 -75.00   0.50    4.00    --  -88.00 -58.00-163.43  170
 60  \w   -160.00 -75.00   0.50    4.00    --  -88.00 -56.00  96.85  170
 61  \w   -164.00 -76.00   0.50    4.00    --  -92.00 -65.00-109.03  176
 62  \w   -164.00 -77.00   0.50    4.00    --  -92.00 -63.00 -67.21  174
 63  \w   -164.00 -77.00   0.50    4.00    --  -92.00 -63.00 -67.21  174
 64  \w   -164.00 -72.00   0.50    4.00    --  -92.00 -74.00   8.40  184
 65  \w   -164.00 -72.00   0.50    4.00    --  -92.00 -74.00   8.40  184
 66  \w   -164.00 -76.00   0.50    4.00    --  -92.00 -65.00-109.03  176
 67  \w   -169.00 -83.00   0.50    4.00    --  -97.00 -59.00 -35.92  172
 68  \w   -169.00 -83.00   0.50    4.00    --  -97.00 -59.00 -35.92  172
 69  \w   -108.00 -25.00   0.50    4.00    --  -97.00  77.00 120.00  166
 70  \w   -169.00 -76.00   0.50    4.00    --  -97.00 -77.00-120.00  186
 71  \w   -169.00 -81.00   0.50    4.00    --  -97.00 -64.00-156.72  176
 72  \w   -169.00 -81.00   0.50    4.00    --  -97.00 -64.00-156.72  176
 73  \w   -169.00 -83.00   0.50    4.00    --  -97.00 -60.00  53.30  172
 74  \w   -169.00 -83.00   0.50    4.00    --  -97.00 -60.00  53.30  172
 75  \w   -167.00 -91.00   0.50    4.00    --  -97.00 -99.00   0.00  152
 76  \w   -169.00 -84.00   0.50    4.00    --  -97.00 -57.00  90.00  170
 77  \w   -169.00 -84.00   0.50    4.00    --  -97.00 -57.00  90.00  170
 78  \w   -169.00 -81.00   0.50    4.00    --  -97.00 -64.00  29.71  176
 79  \w   -169.00 -81.00   0.50    4.00    --  -97.00 -64.00  29.71  176
 80  \w    -68.00 -25.00   0.50    4.00    --  -97.00  57.00  30.00   86
 81  \w   -111.00 -28.00   0.50    4.00    --  -97.00 125.00-180.00  166
 82  \w   -169.00 -80.00   0.50    4.00    --  -97.00 -68.00 -77.16  178
 83  \w   -169.00 -76.00   0.50    4.00    --  -97.00 -77.00-120.00  186
 84  \w   -169.00 -80.00   0.50    4.00    --  -97.00 -68.00 -77.16  178
 85  \w   -169.00 -76.00   0.50    4.00    --  -97.00 -77.00-150.00  186
 86  \w   -169.00 -78.00   0.50    4.00    --  -97.00 -73.00 164.01  182
 87  \w   -169.00 -78.00   0.50    4.00    --  -97.00 -73.00 164.01  182
 88  \w     84.00 175.00   0.50    4.00    --  104.77  77.00  60.00  182
 89  \w     36.00 111.00   0.50    4.00    --  104.77-125.00 -60.00  150
 90  \w     36.00 111.00   0.50    4.00    --  104.77-125.00-180.00  150
 91  \w     84.00 175.00   0.50    4.00    --  104.77  77.00 120.00  182
 92  \w     35.00 106.00   0.50    4.00    --  104.77 -99.00   0.00  142
 93  \w     33.00  64.00   0.50    4.00    --  104.77 -57.00 150.00   62
 94  \w     35.00 106.00   0.50    4.00    --  104.77 -99.00 -90.00  142
 95  \w     35.00 106.00   0.50    4.00    --  104.77 -99.00  60.00  142
 96  \w     35.00 106.00   0.50    4.00    --  104.77 -99.00  60.00  142
 97  \w     33.00 104.00   0.50    4.00    --  104.77 -77.00 -90.00  142
 98  \w     33.00 104.00   0.50    4.00    --  104.77 -77.00 -90.00  142
 99  \w    -23.00  96.00   0.50    1.20    --   48.16   0.00-150.00  238
100  \w    -23.00  96.00   0.50    1.20    --   48.16   0.00-180.00  238
101  \w    -23.00  81.00   0.50    1.20    --   48.16   0.00-120.00  208
102  \w     28.00 119.00   0.50    1.20    --   48.16  77.00 -60.00  182
103  \w     37.00 128.00   0.50    1.20    --   56.00  73.00 170.18  182
104  \w     38.00 128.00   0.50    1.20    --   56.00  70.00 161.78  180
105  \w     39.00 131.00   0.50    1.20    --   60.00  78.00-168.33  184
106  \w   -136.00 -46.00   0.50    1.20    --  -64.00 -70.00 123.47  180
107  \w   -139.00 -51.00   0.50    1.20    --  -68.00 -67.00 130.86  176
108  \w   -144.00 -55.00   0.50    1.20    --  -72.00 -67.00  -3.17  178
;
_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      -0.0741617000
_diffrn_orient_matrix_UB_12      0.0011225000
_diffrn_orient_matrix_UB_13      0.1387536000
_diffrn_orient_matrix_UB_21      0.0841649000
_diffrn_orient_matrix_UB_22      -0.1640314000
_diffrn_orient_matrix_UB_23      0.0011035000
_diffrn_orient_matrix_UB_31      0.2887488000
_diffrn_orient_matrix_UB_32      0.0398250000
_diffrn_orient_matrix_UB_33      0.0028778000
_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  0.0585
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.942
_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       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            36569
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.937
_diffrn_reflns_theta_min         3.983
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.302
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33589
_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    1.480
_exptl_crystal_description       plate
_exptl_crystal_F_000             240
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2065
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0752
_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^)+(0.0723P)^2^+1.6014P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2078
_refine_ls_wR_factor_ref         0.2086
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1967
_reflns_number_total             2065
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc03215f2.cif
_cod_data_source_block           250220_mt-benzoperylene_plate_300k
_cod_depositor_comments
'Adding full bibliography for 1575279--1575293.cif.'
_cod_database_code               1575284
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHS
_diffrn_oxdiff_digest_hkl
;
43e8d28cdd56a1328f9ba05f4a45ac5f93d211
;
_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: H10(0.5) H3(0.5) C14(0.5) H14(0.5) C2(0.5) H2(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C3(H3), C8(H8), C14(H14), C2(H2)
3.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              36975
_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 2.154
_oxdiff_exptl_absorpt_empirical_full_min 0.619