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_1575280
_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 O4'
_chemical_formula_sum            'C28 H20 O4'
_chemical_formula_weight         420.44
_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             2024-10-22
_audit_creation_method
;
Olex2 1.5-ac6-020
(compiled 2024.02.14 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6966)
;
_audit_update_record
;
2025-04-25 deposited with the CCDC.	2025-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.074(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8606(3)
_cell_length_b                   12.9849(4)
_cell_length_c                   13.7224(4)
_cell_measurement_reflns_used    3980
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.5750
_cell_measurement_theta_min      4.6610
_cell_volume                     1885.02(10)
_computing_cell_refinement       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.958
_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    -63.00  24.00   0.50    0.70    --  -47.91  65.00  53.00  174
  2  \w     32.00 120.00   0.50    0.70    --   47.91  65.00  53.00  176
  3  \w    -23.00  64.00   0.50    0.70    --   47.91 -65.00 -82.00  174
  4  \w    -23.00  64.00   0.50    0.70    --   47.91 -65.00 -82.00  174
  5  \w    -79.00 -25.00   0.50    3.00    --  -97.00  65.00  53.00  108
  6  \w   -169.00 -81.00   0.50    3.00    --  -97.00 -65.00 -82.00  176
  7  \w     89.00 175.00   0.50    3.00    --  104.77  65.00  53.00  172
  8  \w     33.00  75.00   0.50    3.00    --  104.77 -65.00 -82.00   84
  9  \w   -120.00 -32.00   0.50    0.70    --  -47.91 -65.00 -82.00  176
 10  \w    -24.00  27.00   0.50    0.70    --   47.91 -19.00 120.00  102
 11  \w    -24.00  27.00   0.50    0.70    --   47.91 -19.00 -90.00  102
 12  \w    -68.00 -25.00   0.50    3.00    --  -97.00  57.00   0.00   86
 13  \w   -104.00 -25.00   0.50    3.00    --  -97.00  77.00-120.00  158
 14  \w    -68.00 -25.00   0.50    3.00    --  -97.00  57.00-120.00   86
 15  \w     33.00 100.00   0.50    3.00    --  104.77 -77.00-180.00  134
 16  \w     33.00  63.00   0.50    3.00    --  104.77 -57.00  60.00   60
 17  \w     92.00 175.00   0.50    3.00    --  104.77  57.00 -30.00  166
 18  \w     33.00  63.00   0.50    3.00    --  104.77 -57.00 -30.00   60
 19  \w     97.00 175.00   0.50    3.00    --  104.77  37.00 -60.00  156
 20  \w     97.00 175.00   0.50    3.00    --  104.77  37.00   0.00  156
 21  \w     33.00  63.00   0.50    3.00    --  104.77 -57.00 120.00   60
 22  \w     33.00 100.00   0.50    3.00    --  104.77 -77.00 -60.00  134
 23  \w     33.00  63.00   0.50    3.00    --  104.77 -57.00 150.00   60
 24  \w     35.00  72.00   0.50    0.70    --   47.91  57.00-180.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0279121000
_diffrn_orient_matrix_UB_12      0.0861641000
_diffrn_orient_matrix_UB_13      0.0791218000
_diffrn_orient_matrix_UB_21      -0.1267526000
_diffrn_orient_matrix_UB_22      -0.0219480000
_diffrn_orient_matrix_UB_23      0.0285206000
_diffrn_orient_matrix_UB_31      0.0659310000
_diffrn_orient_matrix_UB_32      -0.0785584000
_diffrn_orient_matrix_UB_33      0.0788380000
_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     0.0476
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20299
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.518
_diffrn_reflns_theta_min         4.707
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.795
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.136a (Rigaku Oxford Diffraction, 2024)
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    1.481
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3856
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0606
_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^)+(0.0671P)^2^+0.7642P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1402
_refine_ls_wR_factor_ref         0.1535
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2731
_reflns_number_total             3856
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc03215f2.cif
_cod_data_source_block           241022_mo-coronene_block_100k_auto
_cod_depositor_comments
'Adding full bibliography for 1575279--1575293.cif.'
_cod_database_code               1575280
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHO
_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:
 C24(H24), C23(H23), C12(H12), C10(H10), C7(H7), C20(H20), C6(H6), C18(H18)
2.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C32(H32A,H32B,H32C), C30(H30A,H30B,H30C), C26(H26A,H26B,
 H26C)
;
_shelx_res_checksum              68665
_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 1.528
_oxdiff_exptl_absorpt_empirical_full_min 0.515