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_1575291
_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 S4'
_chemical_formula_sum            'C26 H20 S4'
_chemical_formula_weight         460.66
_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             2025-02-20
_audit_creation_method
;
Olex2 1.5-ac7-013
(compiled 2025.01.02 svn.rf662f148 for Rigaku Oxford Diffraction, GUI svn.r7109)
;
_audit_update_record
;
2025-04-25 deposited with the CCDC.	2025-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                89.351(3)
_cell_angle_beta                 77.263(3)
_cell_angle_gamma                87.865(2)
_cell_formula_units_Z            1
_cell_length_a                   5.0737(2)
_cell_length_b                   9.0307(2)
_cell_length_c                   11.3090(5)
_cell_measurement_reflns_used    5310
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.0280
_cell_measurement_theta_min      3.9680
_cell_volume                     505.06(3)
_computing_cell_refinement       'CrysAlisPro 1.171.44.94a (Rigaku OD, 2025)'
_computing_data_collection
'CrysAlisPro system (CCD 44.94a 64-bit (release 17-02-2025))'
_computing_data_reduction        'CrysAlisPro 1.171.44.94a (Rigaku OD, 2025)'
_computing_molecular_graphics    'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_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 0.990
_diffrn_measured_fraction_theta_max 0.924
_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    -68.00 -25.00   0.50    0.05    --  -97.00  57.00-150.00   86
  2  \w   -108.00 -25.00   0.50    0.05    --  -97.00  77.00  30.00  166
  3  \w    -68.00 -25.00   0.50    0.05    --  -97.00  57.00   0.00   86
  4  \w   -169.00 -49.00   0.50    0.05    --  -97.00   0.00  60.00  240
  5  \w   -169.00 -49.00   0.50    0.05    --  -97.00   0.00  60.00  240
  6  \w    -29.00  26.00   0.50    0.05    --  -47.91  19.00 -30.00  110
  7  \w    -29.00  26.00   0.50    0.05    --  -47.91  19.00 -60.00  110
  8  \w    -29.00  26.00   0.50    0.05    --  -47.91  19.00-120.00  110
  9  \w     21.00  96.00   0.50    0.05    --   47.91-132.00 -35.00  150
 10  \w     35.00 117.00   0.50    0.05    --  104.77-132.00 -35.00  164
 11  \w     24.00 100.00   0.50    0.05    --   47.91-137.00 147.00  152
 12  \w     33.00 120.00   0.50    0.05    --  104.77-137.00 147.00  174
 13  \w     36.00 111.00   0.50    0.05    --  104.77-125.00 150.00  150
 14  \w     33.00 104.00   0.50    0.05    --  104.77 -77.00 150.00  142
 15  \w     33.00  64.00   0.50    0.05    --  104.77 -57.00 120.00   62
 16  \w     33.00 104.00   0.50    0.05    --  104.77 -77.00 120.00  142
 17  \w     33.00  64.00   0.50    0.05    --  104.77 -57.00  30.00   62
 18  \w     33.00  64.00   0.50    0.05    --  104.77 -57.00 -30.00   62
 19  \w     33.00  64.00   0.50    0.05    --  104.77 -57.00 -90.00   62
 20  \w     33.00  64.00   0.50    0.05    --  104.77 -57.00-150.00   62
 21  \w    -24.00  24.00   0.50    0.05    --   47.91 -19.00 -60.00   96
 22  \w    -24.00  24.00   0.50    0.05    --   47.91 -19.00-120.00   96
 23  \w     68.00 120.00   0.50    0.05    --   47.91 137.00-148.00  104
 24  \w     68.00 175.00   0.50    0.05    --  104.77 137.00-148.00  214
 25  \w     72.00 175.00   0.50    0.05    --  104.77 132.00  34.00  206
 26  \w     72.00 118.00   0.50    0.05    --   47.91 132.00  34.00   92
 27  \w   -116.00 -27.00   0.50    0.05    --  -97.00 132.00  34.00  178
 28  \w    -96.00 -27.00   0.50    0.05    --  -47.91 132.00  34.00  138
 29  \w   -100.00 -29.00   0.50    0.05    --  -47.91 137.00-148.00  142
 30  \w   -120.00 -29.00   0.50    0.05    --  -97.00 137.00-148.00  182
 31  \w   -120.00 -29.00   0.50    0.05    --  -97.00 137.00-148.00  182
 32  \w   -170.00 -89.00   0.50    0.05    --  -97.00 -19.00-180.00  162
 33  \w   -169.00 -89.00   0.50    0.05    --  -97.00 -37.00 -90.00  160
 34  \w   -169.00 -74.00   0.50    0.05    --  -97.00-137.00 147.00  190
 35  \w   -120.00 -74.00   0.50    0.05    --  -47.91-137.00 147.00   92
 36  \w   -169.00 -84.00   0.50    0.05    --  -97.00 -57.00  30.00  170
 37  \w   -167.00 -91.00   0.50    0.05    --  -97.00 -99.00 -30.00  152
 38  \w   -167.00 -91.00   0.50    0.05    --  -97.00 -99.00 -90.00  152
 39  \w   -167.00 -78.00   0.50    0.05    --  -97.00-132.00 -35.00  178
 40  \w   -120.00 -35.00   0.50    0.05    --  -47.91 -57.00-120.00  170
 41  \w   -120.00 -27.00   0.50    0.05    --  -47.91 -77.00 -30.00  186
 42  \w   -120.00 -69.00   0.50    0.05    --  -47.91 -57.00  30.00  102
 43  \w   -120.00 -27.00   0.50    0.05    --  -47.91 -77.00 120.00  186
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, SynergyCustom DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0629616000
_diffrn_orient_matrix_UB_12      -0.0016235000
_diffrn_orient_matrix_UB_13      0.1396359000
_diffrn_orient_matrix_UB_21      0.0856136000
_diffrn_orient_matrix_UB_22      -0.1655605000
_diffrn_orient_matrix_UB_23      -0.0014776000
_diffrn_orient_matrix_UB_31      0.2928025000
_diffrn_orient_matrix_UB_32      0.0415891000
_diffrn_orient_matrix_UB_33      -0.0022606000
_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  0.0620
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11239
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.642
_diffrn_reflns_theta_min         4.008
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.402
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44710
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.44.94a (Rigaku Oxford Diffraction, 2025)
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    1.515
_exptl_crystal_description       plate
_exptl_crystal_F_000             240
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.182
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1993
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.182
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0771
_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^)+3.3564P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1796
_refine_ls_wR_factor_ref         0.1814
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1821
_reflns_number_total             1993
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc03215f2.cif
_cod_data_source_block           250220_mt-benzoperylene_plate_100k
_cod_depositor_comments
'Adding full bibliography for 1575279--1575293.cif.'
_cod_database_code               1575291
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHS
_chemical_oxdiff_usercomment     'CSD: QIKNAZ'
_diffrn_oxdiff_digest_hkl
;
4399037a40736df485d4b5c3f8f5edbc4b4eee
;
_diffrn_oxdiff_digest_od_ed
;

;
_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: H003(0.5) H006(0.5) C00F(0.5) H00H(0.5) C00G(0.5) H00I(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C003(H003), C004(H004), C006(H006), C00B(H00B), C00F(H00H), C00G(H00I)
3.b Idealised Me refined as rotating group:
 C00D(H00A,H00C,H00D), C00E(H00E,H00F,H00G)
;
_shelx_res_checksum              41827
_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 1.574
_oxdiff_exptl_absorpt_empirical_full_min 0.589