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_1575281
_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                 102.816(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9191(4)
_cell_length_b                   13.1598(6)
_cell_length_c                   13.7566(5)
_cell_measurement_reflns_used    3234
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      74.9640
_cell_measurement_theta_min      4.6470
_cell_volume                     1927.48(13)
_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      300(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.957
_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   -120.00 -32.00   0.50    0.80    --  -47.91 -66.00 -80.00  176
  2  \w    -64.00  24.00   0.50    0.80    --  -47.91  66.00  53.00  176
  3  \w    -23.00  64.00   0.50    0.80    --   47.91 -66.00 -80.00  174
  4  \w    -81.00 -25.00   0.50    2.00    --  -97.00  66.00  53.00  112
  5  \w   -169.00 -81.00   0.50    2.00    --  -97.00 -66.00 -80.00  176
  6  \w     89.00 175.00   0.50    2.00    --  104.77  66.00  53.00  172
  7  \w     33.00  76.00   0.50    2.00    --  104.77 -66.00 -80.00   86
  8  \w     89.00 175.00   0.50    2.00    --  104.77  66.00  53.00  172
  9  \w    -24.00  27.00   0.50    0.80    --   47.91 -19.00 120.00  102
 10  \w     32.00 120.00   0.50    0.80    --   47.91  66.00  53.00  176
 11  \w    -24.00  27.00   0.50    0.80    --   47.91 -19.00 -90.00  102
 12  \w   -169.00 -89.00   0.50    2.00    --  -97.00 -37.00 150.00  160
 13  \w    -68.00 -25.00   0.50    2.00    --  -97.00  57.00-120.00   86
 14  \w   -104.00 -25.00   0.50    2.00    --  -97.00  77.00-120.00  158
 15  \w     33.00  63.00   0.50    2.00    --  104.77 -57.00-180.00   60
 16  \w     35.00 106.00   0.50    2.00    --  104.77 -99.00   0.00  142
 17  \w     92.00 175.00   0.50    2.00    --  104.77  57.00 -30.00  166
 18  \w     33.00  63.00   0.50    2.00    --  104.77 -57.00   0.00   60
 19  \w     97.00 175.00   0.50    2.00    --  104.77  37.00  90.00  156
 20  \w     97.00 175.00   0.50    2.00    --  104.77  37.00   0.00  156
 21  \w     33.00  63.00   0.50    2.00    --  104.77 -57.00 150.00   60
 22  \w     33.00  63.00   0.50    2.00    --  104.77 -57.00 -60.00   60
 23  \w   -120.00 -77.00   0.50    0.80    --  -47.91 -57.00-180.00   86
;
_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      0.0244663000
_diffrn_orient_matrix_UB_12      0.0884539000
_diffrn_orient_matrix_UB_13      0.0750757000
_diffrn_orient_matrix_UB_21      -0.1264019000
_diffrn_orient_matrix_UB_22      -0.0213754000
_diffrn_orient_matrix_UB_23      0.0283430000
_diffrn_orient_matrix_UB_31      0.0660754000
_diffrn_orient_matrix_UB_32      -0.0736265000
_diffrn_orient_matrix_UB_33      0.0821447000
_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  0.0704
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20840
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.915
_diffrn_reflns_theta_min         4.695
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.777
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69107
_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    1.449
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3939
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1170
_refine_ls_R_factor_gt           0.0602
_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^)+(0.0689P)^2^+0.2594P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1348
_refine_ls_wR_factor_ref         0.1585
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2253
_reflns_number_total             3939
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc03215f2.cif
_cod_data_source_block           241022_mo-coronene_block_300k_auto
_cod_depositor_comments
'Adding full bibliography for 1575279--1575293.cif.'
_cod_original_cell_volume        1927.47(13)
_cod_database_code               1575281
_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:
 C12(H12), C20(H20), C17(H17), C26(H26), C11(H11), C22(H22), C19(H19), C6(H6)
2.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C30(H30A,H30B,H30C), C28(H28A,H28B,H28C), C32(H32A,H32B,
 H32C)
;
_shelx_res_checksum              7699
_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 2.189
_oxdiff_exptl_absorpt_empirical_full_min 0.516