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_1575290
_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      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             2023-10-04
_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                90
_cell_angle_beta                 91.678(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7680(4)
_cell_length_b                   10.9262(3)
_cell_length_c                   17.4458(5)
_cell_measurement_reflns_used    4289
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      77.1630
_cell_measurement_theta_min      4.0070
_cell_volume                     1861.14(11)
_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 2018/2 (Sheldrick, 2018)'
_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 0.962
_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   -118.00 -37.00   0.50    1.50    --  -47.66  -4.00-176.00  162
  2  \w    -41.00  24.00   0.50    1.50    --  -47.66   4.00   0.00  130
  3  \w    -23.00  37.00   0.50    1.50    --   47.66  -4.00-176.00  120
  4  \w     37.00 119.00   0.50    1.50    --   47.66   4.00   0.00  164
  5  \w   -169.00 -86.00   0.50    6.00    --  -97.00  -4.00-176.00  166
  6  \w     94.00 175.00   0.50    6.00    --  104.77   4.00   0.00  162
  7  \w    -91.00 -23.00   0.50    1.50    --  -47.66 125.00  90.00  136
  8  \w    -25.00  24.00   0.50    1.50    --   47.66 -19.00 -60.00   98
  9  \w   -170.00 -89.00   0.50    6.00    --  -97.00 -19.00  90.00  162
 10  \w   -109.00 -25.00   0.50    6.00    --  -97.00  77.00 150.00  168
 11  \w   -169.00 -81.00   0.50    6.00    --  -97.00 -64.00 -66.21  176
 12  \w     33.00  64.00   0.50    6.00    --  104.77 -57.00 -30.00   62
 13  \w     36.00 111.00   0.50    6.00    --  104.77-125.00  60.00  150
 14  \w     33.00  64.00   0.50    6.00    --  104.77 -57.00  30.00   62
 15  \w     35.00 106.00   0.50    6.00    --  104.77 -99.00  60.00  142
 16  \w     35.00 106.00   0.50    6.00    --  104.77 -99.00 150.00  142
 17  \w     33.00  64.00   0.50    6.00    --  104.77 -57.00   0.00   62
 18  \w     33.00 105.00   0.50    6.00    --  104.77 -77.00 -30.00  144
 19  \w     35.00 106.00   0.50    6.00    --  104.77 -99.00  90.00  142
 20  \w     35.00 106.00   0.50    6.00    --  104.77 -99.00 -90.00  142
 21  \w     27.00  71.00   0.50    1.50    --   47.66  77.00   0.00   88
;
_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      0.1358122000
_diffrn_orient_matrix_UB_12      -0.0014138000
_diffrn_orient_matrix_UB_13      -0.0427577000
_diffrn_orient_matrix_UB_21      -0.0802272000
_diffrn_orient_matrix_UB_22      0.0078280000
_diffrn_orient_matrix_UB_23      -0.0772000000
_diffrn_orient_matrix_UB_31      0.0057581000
_diffrn_orient_matrix_UB_32      0.1407310000
_diffrn_orient_matrix_UB_33      0.0038801000
_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  0.0512
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17934
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.383
_diffrn_reflns_theta_min         4.776
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.767
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52298
_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    1.415
_exptl_crystal_description       plate
_exptl_crystal_F_000             832
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3813
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.162
_refine_ls_R_factor_all          0.1206
_refine_ls_R_factor_gt           0.0888
_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^)+(0.0444P)^2^+2.0781P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1880
_refine_ls_wR_factor_ref         0.2028
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2711
_reflns_number_total             3813
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc03215f2.cif
_cod_data_source_block           231004_mo-benzoperylene_plate_300k_auto
_cod_depositor_comments
'Adding full bibliography for 1575279--1575293.cif.'
_cod_database_code               1575290
_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: H5(0.45) H8(0.45) H22(0.55) H14(0.55) C7(0.55) H7(0.55) C6(0.55)
 H6(0.55) C24(0.45) H24(0.45) C23(0.45) H23(0.45)
3.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C22(H22), C14(H14), C18(H18), C10(H10), C20(H20), C12(H12),
 C7(H7), C6(H6), C24(H24), C23(H23)
3.b Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C28(H28A,H28B,H28C), C26(H26A,H26B,H26C), C30(H30A,H30B,
 H30C)
;
_shelx_res_checksum              18091
_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 1.887
_oxdiff_exptl_absorpt_empirical_full_min 0.551