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_1569181
_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         'C84 H80 O4'
_chemical_formula_sum            'C84 H80 O4'
_chemical_formula_weight         1153.48
_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             2023-04-25
_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                94.57(2)
_cell_angle_beta                 104.856(10)
_cell_angle_gamma                96.380(13)
_cell_formula_units_Z            1
_cell_length_a                   8.553(2)
_cell_length_b                   11.731(3)
_cell_length_c                   15.988(6)
_cell_measurement_reflns_used    6089
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.137
_cell_measurement_theta_min      2.876
_cell_volume                     1531.1(8)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            28547
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.467
_diffrn_reflns_theta_min         2.878
_exptl_absorpt_coefficient_mu    0.576
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0762 before and 0.0606 after correction.
The Ratio of minimum to maximum transmission is 0.9064.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         5609
_refine_ls_number_restraints     84
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0501
_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^)+(0.0822P)^2^+0.2676P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1345
_refine_ls_wR_factor_ref         0.1509
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3995
_reflns_number_total             5609
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc01295f2.cif
_cod_data_source_block           t_a
_cod_depositor_comments
'Adding full bibliography for 1569181--1569184.cif.'
_cod_database_code               1569181
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.934
_shelx_estimated_absorpt_t_min   0.913
_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. Uiso/Uaniso restraints and constraints
Uanis(C31) \\sim Ueq, Uanis(C32A) \\sim Ueq, Uanis(C33A) \\sim Ueq, Uanis(C42A)
\\sim Ueq, Uanis(C32B) \\sim Ueq, Uanis(C33B) \\sim Ueq, Uanis(C42B) \\sim Ueq,
Uanis(C31A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Rigid body (RIGU) restrains
 C31, C31A, C32A, C32B, C33A, C33B, C42A, C42B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C31A)=Sof(C32B)=Sof(H32D)=Sof(H32E)=Sof(H32F)=Sof(C33B)=Sof(H33D)=
 Sof(H33E)=Sof(H33F)=Sof(C42B)=Sof(H42D)=Sof(H42E)=Sof(H42F)=1-FVAR(1)
 Sof(C31)=Sof(C32A)=Sof(H32A)=Sof(H32B)=Sof(H32C)=Sof(C33A)=Sof(H33A)=
 Sof(H33B)=Sof(H33C)=Sof(C42A)=Sof(H42A)=Sof(H42B)=Sof(H42C)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C34(H34A,H34B), C35(H35A,H35B), C36(H36A,H36B), C38(H38A,H38B), C39(H39A,
 H39B), C40(H40A,H40B)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C9(H9), C11(H11), C12(H12), C17(H17), C20(H20),
 C23(H23), C26(H26), C27(H27), C29(H29), C30(H30)
5.c Idealised Me refined as rotating group:
 C32A(H32A,H32B,H32C), C32B(H32D,H32E,H32F), C33A(H33A,H33B,H33C), C33B(H33D,
 H33E,H33F), C37(H37A,H37B,H37C), C41(H41A,H41B,H41C), C42A(H42A,H42B,H42C),
 C42B(H42D,H42E,H42F)
;
_shelx_res_checksum              3581
_shelx_hkl_checksum              82811
_olex2_submission_special_instructions 'No special instructions were received'