#------------------------------------------------------------------------------
#$Date: 2025-10-06 11:00:06 +0300 (Mon, 06 Oct 2025) $
#$Revision: 302547 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/52/1575283.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1575283
loop_
_publ_author_name
'Pal, Prasanta'
'Bulgarevich, Kirill'
'Hanaki, Ryota'
'Kawabata, Kohsuke'
'Takimiya, Kazuo'
_publ_section_title
;
 Extension of the π-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                 92.011(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6782(4)
_cell_length_b                   10.8375(4)
_cell_length_c                   17.2665(6)
_cell_measurement_reflns_used    4044
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.5410
_cell_measurement_theta_min      4.0730
_cell_volume                     1809.92(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 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 0.995
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  25.00   0.50    1.00    --  -47.66  12.00  64.00  100
  2  ω   -120.00 -40.00   0.50    1.00    --  -47.66 -12.00-107.00  160
  3  ω    -24.00  21.00   0.50    1.00    --   47.66 -12.00-107.00   90
  4  ω     40.00 120.00   0.50    1.00    --   47.66  12.00  64.00  160
  5  ω   -169.00 -89.00   0.50    4.00    --  -97.00 -12.00-107.00  160
  6  ω     97.00 175.00   0.50    4.00    --  104.77  12.00  64.00  156
  7  ω    -91.00 -23.00   0.50    1.00    --  -47.66 125.00-150.00  136
  8  ω    -25.00  24.00   0.50    1.00    --   47.66 -19.00 -90.00   98
  9  ω   -166.00 -82.00   0.50    4.00    --  -97.00-125.00  60.00  168
 10  ω    -68.00 -25.00   0.50    4.00    --  -97.00  57.00  30.00   86
 11  ω    -68.00 -25.00   0.50    4.00    --  -97.00  57.00 -60.00   86
 12  ω   -170.00 -89.00   0.50    4.00    --  -97.00 -19.00 -30.00  162
 13  ω    -68.00 -25.00   0.50    4.00    --  -97.00  57.00   0.00   86
 14  ω    -68.00 -25.00   0.50    4.00    --  -97.00  57.00  60.00   86
 15  ω     33.00 105.00   0.50    4.00    --  104.77 -77.00 150.00  144
 16  ω     33.00  64.00   0.50    4.00    --  104.77 -57.00 120.00   62
 17  ω     35.00 106.00   0.50    4.00    --  104.77 -99.00 -90.00  142
 18  ω     36.00 111.00   0.50    4.00    --  104.77-125.00 -30.00  150
 19  ω     36.00 111.00   0.50    4.00    --  104.77-125.00 -90.00  150
 20  ω     27.00 119.00   0.50    1.00    --   47.66  77.00  60.00  184
 21  ω     27.00 119.00   0.50    1.00    --   47.66  77.00 150.00  184
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1349648000
_diffrn_orient_matrix_UB_12      -0.0206297000
_diffrn_orient_matrix_UB_13      -0.0427886000
_diffrn_orient_matrix_UB_21      -0.0808228000
_diffrn_orient_matrix_UB_22      0.0081149000
_diffrn_orient_matrix_UB_23      -0.0783121000
_diffrn_orient_matrix_UB_31      0.0244101000
_diffrn_orient_matrix_UB_32      0.1405178000
_diffrn_orient_matrix_UB_33      -0.0018778000
_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  0.0707
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_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            16040
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.496
_diffrn_reflns_theta_min         4.819
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.788
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66359
_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    1.455
_exptl_crystal_description       plate
_exptl_crystal_F_000             832
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.208
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3601
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.208
_refine_ls_R_factor_all          0.1205
_refine_ls_R_factor_gt           0.0993
_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/[σ²(Fo²)+(0.0471P)²+4.5017P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2067
_refine_ls_wR_factor_ref         0.2171
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2937
_reflns_number_total             3601
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5sc03215f2.cif
_cod_data_source_block           231004_mo-benzoperylene_plate_100k
_cod_depositor_comments
'Adding full bibliography for 1575279--1575293.cif.'
_cod_database_code               1575283
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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: H006(0.45) H00B(0.45) H00M(0.55) H00O(0.55) C00T(0.55) H00T(0.55)
 C00U(0.55) H00U(0.55) C00V(0.45) H00V(0.45) C00W(0.45) H00W(0.45)
3.a Aromatic/amide H refined with riding coordinates:
 C006(H006), C00B(H00B), C00E(H00E), C00G(H00G), C00L(H00L), C00M(H00M),
 C00O(H00O), C00P(H00P), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W)
3.b Idealised Me refined as rotating group:
 C00N(H00A,H00C,H00D), C00Q(H00F,H00H,H00I), C00R(H00J,H00K,H00N), C00S(H00Q,
 H00R,H00S)
;
_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 1.775
_oxdiff_exptl_absorpt_empirical_full_min 0.635
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.7699(3) 0.7173(3) 0.29664(15) 0.0288(6) Uani 1 1 d . . . . .
O002 O 0.8724(3) 0.2686(2) 0.57649(15) 0.0281(6) Uani 1 1 d . . . . .
O003 O 0.0476(3) 0.5285(3) 0.24651(16) 0.0319(7) Uani 1 1 d . . . . .
O004 O 0.1491(3) 0.0802(3) 0.52492(15) 0.0304(7) Uani 1 1 d . . . . .
C005 C 0.5734(4) 0.4774(4) 0.3905(2) 0.0239(8) Uani 1 1 d . . . . .
C006 C 0.7241(4) 0.3674(4) 0.4864(2) 0.0258(8) Uani 1 1 d . . . . .
H006 H 0.800018 0.417610 0.472779 0.031 Uiso 0.45 1 calc R U P A 2
C007 C 0.2620(4) 0.1518(4) 0.5112(2) 0.0257(8) Uani 1 1 d . . . . .
C008 C 0.6587(4) 0.6446(4) 0.3107(2) 0.0247(8) Uani 1 1 d . . . . .
C009 C 0.4212(4) 0.5778(4) 0.2926(2) 0.0246(8) Uani 1 1 d . . . . .
C00A C 0.7410(4) 0.2750(4) 0.5444(2) 0.0256(8) Uani 1 1 d . . . . .
C00B C 0.6819(4) 0.5534(4) 0.3696(2) 0.0250(8) Uani 1 1 d . . . . .
H00B H 0.770708 0.544733 0.394300 0.030 Uiso 0.45 1 calc R U P B 2
C00C C 0.3463(4) 0.3229(4) 0.4350(2) 0.0252(8) Uani 1 1 d . . . . .
C00D C 0.5934(4) 0.3836(4) 0.4492(2) 0.0240(8) Uani 1 1 d . . . . .
C00E C 0.6337(4) 0.2006(4) 0.5642(2) 0.0248(8) Uani 1 1 d . . . . .
H00E H 0.647450 0.139418 0.603155 0.030 Uiso 1 1 calc R U . . .
C00F C 0.4806(4) 0.3072(4) 0.4701(2) 0.0255(8) Uani 1 1 d . . . . .
C00G C 0.3908(4) 0.1362(4) 0.5460(2) 0.0258(8) Uani 1 1 d . . . . .
H00G H 0.405674 0.072511 0.583188 0.031 Uiso 1 1 calc R U . . .
C00H C 0.5013(4) 0.2147(4) 0.5266(2) 0.0250(8) Uani 1 1 d . . . . .
C00I C 0.1790(4) 0.5215(4) 0.2778(2) 0.0262(8) Uani 1 1 d . . . . .
C00J C 0.4395(4) 0.4886(3) 0.3524(2) 0.0240(8) Uani 1 1 d . . . . .
C00K C 0.3253(4) 0.4164(4) 0.3748(2) 0.0253(8) Uani 1 1 d . . . . .
C00L C 0.5318(4) 0.6540(4) 0.2721(2) 0.0247(8) Uani 1 1 d . . . . .
H00L H 0.519144 0.712411 0.231453 0.030 Uiso 1 1 calc R U . . .
C00M C 0.1953(4) 0.4343(4) 0.3387(2) 0.0268(9) Uani 1 1 d . . . . .
H00M H 0.118040 0.388235 0.355007 0.032 Uiso 0.55 1 calc R U P C 1
C00N C 0.1660(4) -0.0194(4) 0.5785(2) 0.0285(9) Uani 1 1 d . . . . .
H00A H 0.238088 -0.075220 0.560941 0.043 Uiso 1 1 calc R U . . .
H00C H 0.078616 -0.064514 0.581574 0.043 Uiso 1 1 calc R U . . .
H00D H 0.192832 0.013310 0.629765 0.043 Uiso 1 1 calc R U . . .
C00O C 0.2378(4) 0.2471(4) 0.4573(2) 0.0265(8) Uani 1 1 d . . . . .
H00O H 0.147197 0.260111 0.435805 0.032 Uiso 0.55 1 calc R U P D 1
C00P C 0.2883(4) 0.5899(4) 0.2548(2) 0.0264(9) Uani 1 1 d . . . . .
H00P H 0.275997 0.646325 0.212978 0.032 Uiso 1 1 calc R U . . .
C00Q C 0.0232(4) 0.6167(4) 0.1858(2) 0.0294(9) Uani 1 1 d . . . . .
H00F H 0.079870 0.595948 0.141734 0.044 Uiso 1 1 calc R U . . .
H00H H 0.047676 0.699299 0.204796 0.044 Uiso 1 1 calc R U . . .
H00I H -0.074776 0.615052 0.169387 0.044 Uiso 1 1 calc R U . . .
C00R C 0.8984(4) 0.1749(4) 0.6335(2) 0.0295(9) Uani 1 1 d . . . . .
H00J H 0.878311 0.093723 0.610683 0.044 Uiso 1 1 calc R U . . .
H00K H 0.839074 0.188471 0.677518 0.044 Uiso 1 1 calc R U . . .
H00N H 0.995591 0.178190 0.651245 0.044 Uiso 1 1 calc R U . . .
C00S C 0.7495(4) 0.8141(4) 0.2416(2) 0.0292(9) Uani 1 1 d . . . . .
H00Q H 0.723123 0.778704 0.190942 0.044 Uiso 1 1 calc R U . . .
H00R H 0.835400 0.861074 0.237441 0.044 Uiso 1 1 calc R U . . .
H00S H 0.675898 0.868939 0.258444 0.044 Uiso 1 1 calc R U . . .
C00T C 0.8302(7) 0.4420(6) 0.4620(4) 0.0213(14) Uani 0.55 1 d . . P E 1
H00T H 0.920079 0.430786 0.484750 0.026 Uiso 0.55 1 calc R U P E 1
C00U C 0.8115(7) 0.5313(6) 0.4065(4) 0.0215(14) Uani 0.55 1 d . . P E 1
H00U H 0.888434 0.579910 0.392457 0.026 Uiso 0.55 1 calc R U P E 1
C00V C 0.1062(9) 0.2828(8) 0.4286(5) 0.0280(19) Uani 0.45 1 d . . P F 2
H00V H 0.027352 0.243445 0.448699 0.034 Uiso 0.45 1 calc R U P F 2
C00W C 0.0862(9) 0.3731(8) 0.3723(5) 0.0272(19) Uani 0.45 1 d . . P F 2
H00W H -0.005703 0.393856 0.356057 0.033 Uiso 0.45 1 calc R U P F 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D5SC03215F 2025
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C008 O001 C00S 117.0(3) . . ?
C00A O002 C00R 116.9(3) . . ?
C00I O003 C00Q 117.0(3) . . ?
C007 O004 C00N 117.9(3) . . ?
C00B C005 C00D 121.0(3) . . ?
C00B C005 C00J 120.5(3) . . ?
C00J C005 C00D 118.5(4) . . ?
C00D C006 C00A 119.2(4) . . ?
C00T C006 C00A 123.9(4) . . ?
C00T C006 C00D 116.9(4) . . ?
O004 C007 C00G 124.9(3) . . ?
O004 C007 C00O 114.6(3) . . ?
C00G C007 C00O 120.5(4) . . ?
O001 C008 C00B 114.9(3) . . ?
O001 C008 C00L 124.4(3) . . ?
C00L C008 C00B 120.7(4) . . ?
C00J C009 C00P 118.9(4) . . ?
C00L C009 C00J 120.3(3) . . ?
C00L C009 C00P 120.8(3) . . ?
O002 C00A C006 113.8(3) . . ?
C00E C00A O002 124.8(3) . . ?
C00E C00A C006 121.4(4) . . ?
C005 C00B C008 119.4(3) . . ?
C005 C00B C00U 116.8(4) . . ?
C00U C00B C008 123.7(4) . . ?
C00F C00C C00K 119.2(4) . . ?
C00O C00C C00F 119.7(3) . . ?
C00O C00C C00K 121.0(4) . . ?
C006 C00D C005 120.2(4) . . ?
C006 C00D C00F 119.7(3) . . ?
C00F C00D C005 120.1(3) . . ?
C00A C00E C00H 120.1(3) . . ?
C00C C00F C00D 121.2(3) . . ?
C00H C00F C00C 119.0(4) . . ?
C00H C00F C00D 119.8(3) . . ?
C007 C00G C00H 120.2(4) . . ?
C00F C00H C00E 119.8(4) . . ?
C00F C00H C00G 120.1(4) . . ?
C00G C00H C00E 120.2(3) . . ?
O003 C00I C00M 114.1(3) . . ?
C00P C00I O003 125.2(3) . . ?
C00P C00I C00M 120.7(4) . . ?
C009 C00J C005 118.5(4) . . ?
C00K C00J C005 121.8(3) . . ?
C00K C00J C009 119.6(4) . . ?
C00J C00K C00C 119.1(4) . . ?
C00M C00K C00C 121.0(4) . . ?
C00M C00K C00J 120.0(4) . . ?
C008 C00L C009 120.4(3) . . ?
C00K C00M C00I 119.9(4) . . ?
C00W C00M C00I 124.1(5) . . ?
C00W C00M C00K 115.6(5) . . ?
C00C C00O C007 120.3(4) . . ?
C00C C00O C00V 115.0(5) . . ?
C00V C00O C007 124.3(5) . . ?
C00I C00P C009 120.8(4) . . ?
C00U C00T C006 123.0(6) . . ?
C00T C00U C00B 122.0(6) . . ?
C00W C00V C00O 122.9(8) . . ?
C00V C00W C00M 122.6(8) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C008 1.363(5) . ?
O001 C00S 1.424(5) . ?
O002 C00A 1.370(5) . ?
O002 C00R 1.430(5) . ?
O003 C00I 1.366(5) . ?
O003 C00Q 1.431(5) . ?
O004 C007 1.368(5) . ?
O004 C00N 1.427(5) . ?
C005 C00B 1.392(6) . ?
C005 C00D 1.444(5) . ?
C005 C00J 1.438(5) . ?
C006 C00A 1.422(5) . ?
C006 C00D 1.409(5) . ?
C006 C00T 1.384(8) . ?
C007 C00G 1.375(6) . ?
C007 C00O 1.405(5) . ?
C008 C00B 1.430(5) . ?
C008 C00L 1.380(5) . ?
C009 C00J 1.421(5) . ?
C009 C00L 1.408(5) . ?
C009 C00P 1.428(5) . ?
C00A C00E 1.369(5) . ?
C00B C00U 1.407(8) . ?
C00C C00F 1.425(5) . ?
C00C C00K 1.461(5) . ?
C00C C00O 1.398(6) . ?
C00D C00F 1.426(6) . ?
C00E C00H 1.424(5) . ?
C00F C00H 1.409(5) . ?
C00G C00H 1.416(6) . ?
C00I C00M 1.420(5) . ?
C00I C00P 1.362(6) . ?
C00J C00K 1.419(5) . ?
C00K C00M 1.397(5) . ?
C00M C00W 1.391(10) . ?
C00O C00V 1.404(10) . ?
C00T C00U 1.369(9) . ?
C00V C00W 1.388(13) . ?
