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_1575293
_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                85.8831(14)
_cell_angle_beta                 76.1584(16)
_cell_angle_gamma                79.9947(18)
_cell_formula_units_Z            8
_cell_length_a                   10.8935(2)
_cell_length_b                   18.7430(4)
_cell_length_c                   18.9847(3)
_cell_measurement_reflns_used    36601
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.3760
_cell_measurement_theta_min      3.2990
_cell_volume                     3704.58(12)
_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      100(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 0.959
_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    -23.00  54.00   0.50    0.30    --   47.91 -50.00 150.00  154
  2  \w     37.00 120.00   0.50    0.30    --   47.91  50.00 -62.00  166
  3  \w    -59.00 -25.00   0.50    1.50    --  -97.00  50.00 -62.00   68
  4  \w   -169.00 -86.00   0.50    1.50    --  -97.00 -50.00 150.00  166
  5  \w     94.00 175.00   0.50    1.50    --  104.77  50.00 -62.00  162
  6  \w    -91.00 -23.00   0.50    0.30    --  -47.91 125.00  60.00  136
  7  \w    -28.00  26.00   0.50    0.30    --  -47.91  19.00-120.00  108
  8  \w    -58.00  24.00   0.50    0.30    --  -47.91  50.00 -62.00  164
  9  \w   -120.00 -37.00   0.50    0.30    --  -47.91 -50.00 150.00  166
 10  \w    -23.00  61.00   0.50    0.30    --   47.91 -57.00-180.00  168
 11  \w    -24.00  24.00   0.50    0.30    --   47.91 -19.00-150.00   96
 12  \w    -24.00  24.00   0.50    0.30    --   47.91 -19.00   0.00   96
 13  \w    -68.00 -25.00   0.50    1.50    --  -97.00  57.00 120.00   86
 14  \w   -169.00 -84.00   0.50    1.50    --  -97.00 -58.00  -9.17  170
 15  \w    -68.00 -25.00   0.50    1.50    --  -97.00  57.00  90.00   86
 16  \w   -169.00 -85.00   0.50    1.50    --  -97.00 -54.00-127.13  168
 17  \w   -111.00 -28.00   0.50    1.50    --  -97.00 125.00 120.00  166
 18  \w   -111.00 -28.00   0.50    1.50    --  -97.00 125.00 -60.00  166
 19  \w    -68.00 -25.00   0.50    1.50    --  -97.00  57.00   0.00   86
 20  \w   -169.00 -87.00   0.50    1.50    --  -97.00 -47.00-145.84  164
 21  \w   -109.00 -25.00   0.50    1.50    --  -97.00  77.00 120.00  168
 22  \w     35.00 106.00   0.50    1.50    --  104.77 -99.00-180.00  142
 23  \w     35.00 106.00   0.50    1.50    --  104.77 -99.00 -90.00  142
 24  \w     36.00 111.00   0.50    1.50    --  104.77-125.00  90.00  150
 25  \w     97.00 175.00   0.50    1.50    --  104.77  19.00  90.00  156
 26  \w     36.00 111.00   0.50    1.50    --  104.77-125.00  60.00  150
 27  \w     36.00 111.00   0.50    1.50    --  104.77-125.00-120.00  150
 28  \w     97.00 175.00   0.50    1.50    --  104.77  37.00  60.00  156
 29  \w     35.00 106.00   0.50    1.50    --  104.77 -99.00  90.00  142
 30  \w     33.00  64.00   0.50    1.50    --  104.77 -57.00  90.00   62
 31  \w     35.00 106.00   0.50    1.50    --  104.77 -99.00 -60.00  142
 32  \w     35.00 106.00   0.50    1.50    --  104.77 -99.00-120.00  142
 33  \w     35.00 106.00   0.50    1.50    --  104.77 -99.00   0.00  142
 34  \w     33.00  64.00   0.50    1.50    --  104.77 -57.00 -60.00   62
 35  \w   -120.00 -27.00   0.50    0.30    --  -47.91 -77.00 -90.00  186
 36  \w     35.00  86.00   0.50    0.30    --   47.91  57.00 120.00  102
 37  \w     27.00 120.00   0.50    0.30    --   47.91  77.00  30.00  186
;
_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      -0.1199502000
_diffrn_orient_matrix_UB_12      -0.0369854000
_diffrn_orient_matrix_UB_13      0.0215361000
_diffrn_orient_matrix_UB_21      0.0366807000
_diffrn_orient_matrix_UB_22      -0.0357783000
_diffrn_orient_matrix_UB_23      -0.0743400000
_diffrn_orient_matrix_UB_31      0.0777957000
_diffrn_orient_matrix_UB_32      -0.0657980000
_diffrn_orient_matrix_UB_33      0.0316377000
_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  0.0414
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.959
_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            71047
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.607
_diffrn_reflns_theta_min         2.395
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.770
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63150
_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    1.422
_exptl_crystal_description       prism
_exptl_crystal_F_000             1664
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1169
_refine_ls_number_reflns         15119
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0482
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0552P)^2^+2.9869P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1364
_refine_ls_wR_factor_ref         0.1406
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12803
_reflns_number_total             15119
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc03215f2.cif
_cod_data_source_block           231005_mo-benzoperylene_prism_100k_auto
_cod_depositor_comments
'Adding full bibliography for 1575279--1575293.cif.'
_cod_original_cell_volume        3704.58(13)
_cod_database_code               1575293
_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: H11(0.25) H17(0.75) H44(0.4) H41(0.4) H35(0.6) H52(0.6) H65(0.75)
 H84(0.25) H5(0.75) H72(0.25) H20(0.25) H79(0.75) H95(0.6) H102(0.4) C19(0.75)
 H19(0.75) H115(0.4) H107(0.6) C18(0.75) H18(0.75) C86(0.75) H86(0.75)
 C85(0.75) H85(0.75) C42(0.6) H42(0.6) C117(0.6) H117(0.6) C43(0.6) H43(0.6)
 C116(0.6) H116(0.6) C53(0.4) H53(0.4) C54(0.4) H54(0.4) C23(0.4) H23(0.4)
 C25(0.4) H25(0.4) C27(0.25) H27(0.25) C29(0.25) H29(0.25) C55(0.25) H55(0.25)
 C57(0.25) H57(0.25)
3.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C15(H15), C17(H17), C44(H44), C41(H41), C37(H37), C35(H35),
 C39(H39), C52(H52), C65(H65), C82(H82), C84(H84), C67(H67), C5(H5), C72(H72),
 C20(H20), C50(H50), C48(H48), C79(H79), C13(H13), C22(H22), C77(H77), C7(H7),
 C74(H74), C104(H104), C95(H95), C109(H109), C97(H97), C102(H102), C19(H19),
 C115(H115), C107(H107), C113(H113), C18(H18), C86(H86), C85(H85), C42(H42),
 C117(H117), C43(H43), C116(H116), C53(H53), C54(H54), C23(H23), C25(H25),
 C27(H27), C29(H29), C55(H55), C57(H57)
3.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C30(H30A,H30B,H30C), C92(H92A,H92B,H92C), C24(H24A,H24B,
 H24C), C26(H26A,H26B,H26C), C56(H56A,H56B,H56C), C62(H62A,H62B,H62C), C81(H81A,
 H81B,H81C), C58(H58A,H58B,H58C), C60(H60A,H60B,H60C), C90(H90A,H90B,H90C),
 C88(H88A,H88B,H88C), C121(H12A,H12B,H12C), C123(H12D,H12E,H12F), C111(H11A,
 H11B,H11C), C119(H11D,H11E,H11F)
;
_shelx_res_checksum              60726
_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 1.456
_oxdiff_exptl_absorpt_empirical_full_min 0.662