From closed-shell edge-extended kekulenes to open-shell carbonylated cycloarene diradicaloid.
Chang, Dongdong; Zhu, Jiangyu; Sun, Yutao; Chi, Kai; Qiao, Yanjun; Wang, Teng; Zhao, Yan; Liu, Yunqi; Lu, Xuefeng; Chemical science 14 (2023) 6087–6094; doi:10.1039/d3sc01295f

data_1569183
_publ_section_title
;
 From closed-shell edge-extended kekulenes to open-shell carbonylated
 cycloarene diradicaloid.
;
_journal_issue                   22
_journal_name_full               'Chemical science'
_journal_page_first              6087
_journal_page_last               6094
_journal_paper_doi               10.1039/d3sc01295f
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C98 H84 O4, 2[CHCl3]'
_chemical_formula_sum            'C100 H86 Cl6 O4'
_chemical_formula_weight         1564.38
_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             2023-04-26
_audit_creation_method
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_audit_update_record
;
2023-04-28 deposited with the CCDC.	2023-05-15 downloaded from the CCDC.
;
_cell_angle_alpha                87.388(4)
_cell_angle_beta                 88.255(6)
_cell_angle_gamma                79.150(7)
_cell_formula_units_Z            1
_cell_length_a                   9.5464(8)
_cell_length_b                   11.1446(7)
_cell_length_c                   19.3904(8)
_cell_measurement_reflns_used    6472
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      77.0300
_cell_measurement_theta_min      4.037
_cell_volume                     2023.5(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.85a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.85a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.85a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \f    -10.27 349.73   1.00   15.00 -19.23-110.11  31.50    --   360
  2  \f   -339.92  20.08   1.00   15.00 -69.43 -95.11 -59.25    --   360
  3  \w   -119.22 -19.22   1.00   15.00    -- -110.11  89.85-168.66  100
  4  \w   -119.22 -19.22   1.00   15.00    -- -110.11  89.85  31.34  100
  5  \w    -88.74   6.26   1.00    5.00    --  -45.19  89.85 167.34   95
  6  \w    238.80 354.80   1.00    5.00    --  -30.19 -59.25-159.92  116
  7  \w    238.80 354.80   1.00    5.00    --  -30.19 -59.25  20.08  116
  8  \w    -88.74   6.26   1.00    5.00    --  -45.19  89.85   7.34   95
  9  \w   -119.22 -19.22   1.00   15.00    -- -110.11  89.85 -32.67  100
 10  \w    223.80 339.80   1.00    5.00    --  -45.19 -59.25 100.08  116
 11  \w   -119.22 -19.22   1.00   15.00    -- -110.11  89.85 127.33  100
 12  \w    223.80 339.80   1.00    5.00    --  -45.19 -59.25 -59.92  116
 13  \f   -349.73  10.27   1.00   15.00 -93.68-110.11 -31.50    --   360
 14  \w   -113.46 -19.46   1.00   15.00    -- -110.11 114.09-148.76   94
 15  \w   -119.22 -19.22   1.00   15.00    -- -110.11  89.85  63.33  100
 16  \w   -119.22 -19.22   1.00   15.00    -- -110.11  89.85 -72.67  100
 17  \f   -339.92  20.08   1.00   15.00 -54.43 -80.11 -59.25    --   360
 18  \w    224.57 320.57   1.00    5.00    --  -65.11 -59.25 -69.92   96
 19  \w    223.57 305.57   1.00   15.00    --  -80.11 -59.25  20.08   82
 20  \w    224.57 320.57   1.00    5.00    --  -65.11 -59.25  20.08   96
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0986625000
_diffrn_orient_matrix_UB_12      -0.1247787000
_diffrn_orient_matrix_UB_13      0.0129367000
_diffrn_orient_matrix_UB_21      -0.0231987000
_diffrn_orient_matrix_UB_22      -0.0346081000
_diffrn_orient_matrix_UB_23      -0.0742587000
_diffrn_orient_matrix_UB_31      0.1293824000
_diffrn_orient_matrix_UB_32      0.0554604000
_diffrn_orient_matrix_UB_33      -0.0254323000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1013
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            38960
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.598
_diffrn_reflns_theta_max         66.598
_diffrn_reflns_theta_min         2.281
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_current           45.0
_diffrn_source_power             2.25
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.357
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.85a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       block
_exptl_crystal_F_000             820
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     465
_refine_ls_number_reflns         7134
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.948
_refine_ls_R_factor_all          0.1176
_refine_ls_R_factor_gt           0.0810
_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^)+(0.1755P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2385
_refine_ls_wR_factor_ref         0.2818
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3854
_reflns_number_total             7134
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc01295f2.cif
_cod_data_source_block           20220221cdd_1_autored_sq
_cod_depositor_comments
'Adding full bibliography for 1569181--1569184.cif.'
_cod_database_code               1569183
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.765
_shelx_estimated_absorpt_t_min   0.704
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C42(H42A,H42B), C43(H43A,H43B), C44(H44A,H44B), C46(H46A,H46B), C47(H47A,
 H47B), C48(H48A,H48B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C11(H11), C14(H14), C15(H15), C16(H16), C19(H19), C22(H22),
 C26(H26), C27(H27), C30(H30), C31(H31), C32(H32), C35(H35), C37(H37)
2.c Idealised Me refined as rotating group:
 C39(H39A,H39B,H39C), C40(H40A,H40B,H40C), C41(H41A,H41B,H41C), C45(H45A,H45B,
 H45C), C49(H49A,H49B,H49C)
;
_shelx_res_checksum              11742
_shelx_hkl_checksum              17885
_shelx_fab_checksum              93843
_platon_squeeze_special_details
;
A solvent mask was calculated and 131 electrons were 
found in a volume of 371\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 
2[CHCl3] per Asymmetric Unit 
which account for 116 electrons 
per unit cell.
;
_platon_squeeze_void_probe_radius 1.20
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.533
_oxdiff_exptl_absorpt_empirical_full_min 0.306