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_1575285
_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 O4'
_chemical_formula_sum            'C26 H20 O4'
_chemical_formula_weight         396.42
_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             2023-10-05
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2025-04-25 deposited with the CCDC.	2025-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                86.1432(16)
_cell_angle_beta                 75.6762(19)
_cell_angle_gamma                79.232(2)
_cell_formula_units_Z            8
_cell_length_a                   10.9983(3)
_cell_length_b                   18.9426(4)
_cell_length_c                   19.1861(3)
_cell_measurement_reflns_used    28214
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      77.1570
_cell_measurement_theta_min      3.3110
_cell_volume                     3803.78(15)
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (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 0.996
_diffrn_measured_fraction_theta_max 0.962
_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 -38.00   0.50    0.50    --  -47.91 -48.00 152.00  164
  2  \w    -56.00  24.00   0.50    0.50    --  -47.91  48.00 -58.00  160
  3  \w    -23.00  52.00   0.50    0.50    --   47.91 -48.00 152.00  150
  4  \w     38.00 120.00   0.50    0.50    --   47.91  48.00 -58.00  164
  5  \w   -169.00 -87.00   0.50    2.00    --  -97.00 -48.00 152.00  164
  6  \w    -56.00 -25.00   0.50    2.00    --  -97.00  48.00 -58.00   62
  7  \w     95.00 175.00   0.50    2.00    --  104.77  48.00 -58.00  160
  8  \w    -91.00 -23.00   0.50    0.50    --  -47.91 125.00-120.00  136
  9  \w    -91.00 -23.00   0.50    0.50    --  -47.91 125.00  60.00  136
 10  \w     40.00 120.00   0.50    0.50    --   47.91  37.00 150.00  160
 11  \w    -23.00  61.00   0.50    0.50    --   47.91 -57.00  30.00  168
 12  \w   -169.00 -76.00   0.50    2.00    --  -97.00 -77.00-134.28  186
 13  \w   -111.00 -28.00   0.50    2.00    --  -97.00 125.00   0.00  166
 14  \w   -169.00 -89.00   0.50    2.00    --  -97.00 -37.00 -60.00  160
 15  \w    -68.00 -25.00   0.50    2.00    --  -97.00  57.00 120.00   86
 16  \w    -68.00 -25.00   0.50    2.00    --  -97.00  57.00 -90.00   86
 17  \w   -167.00 -91.00   0.50    2.00    --  -97.00 -99.00 120.00  152
 18  \w    -68.00 -25.00   0.50    2.00    --  -97.00  57.00  30.00   86
 19  \w   -169.00 -89.00   0.50    2.00    --  -97.00 -37.00   0.00  160
 20  \w    -68.00 -25.00   0.50    2.00    --  -97.00  57.00 150.00   86
 21  \w   -166.00 -82.00   0.50    2.00    --  -97.00-125.00 150.00  168
 22  \w     36.00 111.00   0.50    2.00    --  104.77-125.00-180.00  150
 23  \w     33.00 105.00   0.50    2.00    --  104.77 -77.00 -90.00  144
 24  \w     97.00 175.00   0.50    2.00    --  104.77  37.00-150.00  156
 25  \w     35.00 106.00   0.50    2.00    --  104.77 -99.00  60.00  142
 26  \w     35.00 106.00   0.50    2.00    --  104.77 -99.00  90.00  142
 27  \w     35.00 107.00   0.50    2.00    --  104.77-104.00-176.35  144
 28  \w     33.00  64.00   0.50    2.00    --  104.77 -57.00-180.00   62
 29  \w     33.00  64.00   0.50    2.00    --  104.77 -57.00 150.00   62
 30  \w     36.00 111.00   0.50    2.00    --  104.77-125.00 -60.00  150
 31  \w     35.00 106.00   0.50    2.00    --  104.77 -99.00   0.00  142
 32  \w     33.00  64.00   0.50    2.00    --  104.77 -57.00 120.00   62
 33  \w     97.00 175.00   0.50    2.00    --  104.77  19.00  60.00  156
 34  \w     35.00 106.00   0.50    2.00    --  104.77 -99.00-120.00  142
 35  \w     35.00 106.00   0.50    2.00    --  104.77 -99.00 -90.00  142
 36  \w     35.00 106.00   0.50    2.00    --  104.77 -99.00 -60.00  142
 37  \w     34.00  64.00   0.50    2.00    --  104.77 -57.00 -60.00   60
 38  \w     51.00  77.00   0.50    2.00    --  104.77 -99.00 120.00   52
 39  \w     33.00  60.00   0.50    2.00    --  104.77 -57.00 -30.00   54
;
_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      -0.1228170000
_diffrn_orient_matrix_UB_12      -0.0325253000
_diffrn_orient_matrix_UB_13      0.0202640000
_diffrn_orient_matrix_UB_21      0.0366941000
_diffrn_orient_matrix_UB_22      -0.0358089000
_diffrn_orient_matrix_UB_23      -0.0738276000
_diffrn_orient_matrix_UB_31      0.0718043000
_diffrn_orient_matrix_UB_32      -0.0671737000
_diffrn_orient_matrix_UB_33      0.0317541000
_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  0.0417
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            73326
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.692
_diffrn_reflns_theta_min         2.375
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.750
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_description       prism
_exptl_crystal_F_000             1664
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1179
_refine_ls_number_reflns         15576
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0533
_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^)+(0.0743P)^2^+1.1698P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1528
_refine_ls_wR_factor_ref         0.1630
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11748
_reflns_number_total             15576
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc03215f2.cif
_cod_data_source_block           231005_mo-benzoperylene_prism_300k_auto
_cod_depositor_comments
'Adding full bibliography for 1575279--1575293.cif.'
_cod_original_cell_volume        3803.79(16)
_cod_database_code               1575285
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O'
_chemical_oxdiff_usercomment     ' '
_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: H42(0.25) H3(0.75) H79(0.4) H34(0.75) H71(0.4) H65(0.6) H62(0.6)
 H22(0.25) H49(0.75) H10(0.25) H39(0.25) H111(0.4) H94(0.6) H15(0.75) H100(0.4)
 H105(0.6) C41(0.75) H41(0.75) C40(0.75) H40(0.75) C23(0.75) H23(0.75)
 C24(0.75) H24(0.75) C92(0.75) H92A(0.75) H92B(0.75) H92C(0.75) C109(0.6)
 H109(0.6) C110(0.6) H110(0.6) C77(0.6) H77(0.6) C78(0.6) H78(0.6) C64(0.4)
 H64(0.4) C93(0.4) H93(0.4) C63(0.4) H63(0.4) C106(0.4) H106(0.4) C18(0.25)
 H18(0.25) C25(0.25) H25(0.25) C27(0.25) H27(0.25) C29(0.25) H29(0.25)
 C47(0.25) H47A(0.25) H47B(0.25) H47C(0.25)
3.a Aromatic/amide H refined with riding coordinates:
 C42(H42), C3(H3), C79(H79), C34(H34), C32(H32), C71(H71), C65(H65), C62(H62),
 C22(H22), C49(H49), C5(H5), C45(H45), C67(H67), C10(H10), C39(H39), C81(H81),
 C20(H20), C83(H83), C53(H53), C111(H111), C94(H94), C15(H15), C69(H69),
 C51(H51), C100(H100), C113(H113), C12(H12), C96(H96), C105(H105), C115(H115),
 C17(H17), C98(H98), C41(H41), C40(H40), C23(H23), C24(H24), C109(H109),
 C110(H110), C77(H77), C78(H78), C64(H64), C93(H93), C63(H63), C106(H106),
 C18(H18), C25(H25), C27(H27), C29(H29)
3.b Idealised Me refined as rotating group:
 C60(H60A,H60B,H60C), C30(H30A,H30B,H30C), C86(H86A,H86B,H86C), C48(H48A,H48B,
 H48C), C56(H56A,H56B,H56C), C58(H58A,H58B,H58C), C88(H88A,H88B,H88C), C26(H26A,
 H26B,H26C), C118(H11A,H11B,H11C), C19(H19A,H19B,H19C), C28(H28A,H28B,H28C),
 C90(H90A,H90B,H90C), C124(H12A,H12B,H12C), C120(H12D,H12E,H12F), C92(H92A,H92B,
 H92C), C122(H12G,H12H,H12I), C47(H47A,H47B,H47C)
;
_shelx_res_checksum              82696
_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 1.363
_oxdiff_exptl_absorpt_empirical_full_min 0.732