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_1575287
_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         'C28 H20 S4'
_chemical_formula_sum            'C28 H20 S4'
_chemical_formula_weight         484.68
_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             2025-02-19
_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                88.844(3)
_cell_angle_beta                 77.845(3)
_cell_angle_gamma                86.230(3)
_cell_formula_units_Z            1
_cell_length_a                   5.2372(2)
_cell_length_b                   8.8932(3)
_cell_length_c                   11.4399(4)
_cell_measurement_reflns_used    3461
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      75.7040
_cell_measurement_theta_min      3.9230
_cell_volume                     519.74(3)
_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  (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 0.994
_diffrn_measured_fraction_theta_max 0.930
_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   -119.00 -71.00   0.50    1.00    --  -48.16-141.00 154.00   96
  2  \w   -103.00 -31.00   0.50    1.00    --  -48.16 141.00-147.00  144
  3  \w    -94.00 -25.00   0.50    1.00    --  -48.16 128.00  40.00  138
  4  \w     65.00 119.00   0.50    1.00    --   48.16 141.00-147.00  108
  5  \w     19.00  94.00   0.50    1.00    --   48.16-128.00 -33.00  150
  6  \w     25.00 103.00   0.50    1.00    --   48.16-141.00 154.00  156
  7  \w   -169.00 -71.00   0.50    4.00    --  -97.00-141.00 154.00  196
  8  \w   -124.00 -31.00   0.50    4.00    --  -97.00 141.00-147.00  186
  9  \w   -167.00 -80.00   0.50    4.00    --  -97.00-128.00 -33.00  174
 10  \w   -114.00 -27.00   0.50    4.00    --  -97.00 128.00  40.00  174
 11  \w     65.00 172.00   0.50    4.00    --  104.77 141.00-147.00  214
 12  \w     35.00 114.00   0.50    4.00    --  104.77-128.00 -33.00  158
 13  \w     33.00 124.00   0.50    4.00    --  104.77-141.00 154.00  182
 14  \w     74.00 175.00   0.50    4.00    --  104.77 128.00  40.00  202
 15  \w    -24.00  24.00   0.50    1.00    --   48.16 -19.00 -60.00   96
 16  \w     28.00 119.00   0.50    1.00    --   48.16  77.00 150.00  182
 17  \w    -24.00  24.00   0.50    1.00    --   48.16 -19.00  30.00   96
 18  \w    -24.00  24.00   0.50    1.00    --   48.16 -19.00-180.00   96
 19  \w    -68.00 -25.00   0.50    4.00    --  -97.00  57.00   0.00   86
 20  \w   -169.00 -84.00   0.50    4.00    --  -97.00 -57.00   0.00  170
 21  \w   -169.00 -84.00   0.50    4.00    --  -97.00 -57.00   0.00  170
 22  \w   -167.00 -91.00   0.50    4.00    --  -97.00 -99.00 -90.00  152
 23  \w   -167.00 -91.00   0.50    4.00    --  -97.00 -99.00 -90.00  152
 24  \w   -166.00 -82.00   0.50    4.00    --  -97.00-125.00  90.00  168
 25  \w   -169.00 -89.00   0.50    4.00    --  -97.00 -37.00-150.00  160
 26  \w   -169.00 -89.00   0.50    4.00    --  -97.00 -37.00 -90.00  160
 27  \w   -166.00 -82.00   0.50    4.00    --  -97.00-125.00  90.00  168
 28  \w     35.00 106.00   0.50    4.00    --  104.77 -99.00   0.00  142
 29  \w     36.00 111.00   0.50    4.00    --  104.77-125.00-150.00  150
 30  \w     33.00  64.00   0.50    4.00    --  104.77 -57.00 -90.00   62
 31  \w     35.00 106.00   0.50    4.00    --  104.77 -99.00 -60.00  142
 32  \w     33.00  64.00   0.50    4.00    --  104.77 -57.00 150.00   62
 33  \w     92.00 175.00   0.50    4.00    --  104.77  57.00 120.00  166
 34  \w     33.00  64.00   0.50    4.00    --  104.77 -57.00-150.00   62
 35  \w     33.00  64.00   0.50    4.00    --  104.77 -57.00-180.00   62
 36  \w     33.00  64.00   0.50    4.00    --  104.77 -57.00   0.00   62
 37  \w     33.00  64.00   0.50    4.00    --  104.77 -57.00 120.00   62
 38  \w   -119.00 -27.00   0.50    1.00    --  -48.16 -77.00  60.00  184
 39  \w   -119.00 -35.00   0.50    1.00    --  -48.16 -57.00 -30.00  168
 40  \w     36.00 119.00   0.50    1.00    --   48.16  57.00  90.00  166
 41  \w     28.00 119.00   0.50    1.00    --   48.16  77.00-150.00  182
 42  \w     28.00  86.00   0.50    1.00    --   48.16  77.00 -30.00  116
 43  \w     28.00 119.00   0.50    1.00    --   48.16  77.00 -90.00  182
;
_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      0.0575172000
_diffrn_orient_matrix_UB_12      -0.0121856000
_diffrn_orient_matrix_UB_13      -0.1373119000
_diffrn_orient_matrix_UB_21      0.2125735000
_diffrn_orient_matrix_UB_22      0.1140534000
_diffrn_orient_matrix_UB_23      -0.0094260000
_diffrn_orient_matrix_UB_31      0.2059328000
_diffrn_orient_matrix_UB_32      -0.1303209000
_diffrn_orient_matrix_UB_33      0.0057821000
_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  0.0546
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11343
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.693
_diffrn_reflns_theta_min         3.953
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.312
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79776
_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    1.549
_exptl_crystal_description       plate
_exptl_crystal_F_000             252
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2068
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0832
_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^)+(0.1178P)^2^+0.7279P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2136
_refine_ls_wR_factor_ref         0.2268
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1648
_reflns_number_total             2068
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc03215f2.cif
_cod_data_source_block           250219_mt-coronene_plate_300k_auto
_cod_depositor_comments
'Adding full bibliography for 1575279--1575293.cif.'
_cod_database_code               1575287
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHS
_chemical_oxdiff_usercomment     ' '
_diffrn_oxdiff_digest_hkl
;
43ffc817a80e8a60332f9a2e33b305698e0617
;
_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.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C8(H8), C14(H14), C2(H2)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              48280
_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 1.343
_oxdiff_exptl_absorpt_empirical_full_min 0.775