Cyclic(alkyl)(amino)carbene (CAAC)- and bicyclic (alkyl)(amino)carbene (BICAAC)-derived glyoxal radical cations with excellent stability.
Das, Bindusagar; Yadav, Ritu; Sharma, Ankita; Karmakar, Tarak; Kundu, Subrata; Chemical communications (Cambridge, England) 59 (2023) 5285–5288; doi:10.1039/d3cc00200d

data_7131511
_publ_section_title
;
 Cyclic(alkyl)(amino)carbene (CAAC)- and bicyclic (alkyl)(amino)carbene
 (BICAAC)-derived glyoxal radical cations with excellent stability.
;
_journal_issue                   35
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5285
_journal_page_last               5288
_journal_paper_doi               10.1039/d3cc00200d
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C46 H66 N2 O2, B F4'
_chemical_formula_sum            'C46 H66 B F4 N2 O2'
_chemical_formula_weight         765.867
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_Int_Tables_number      15
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-12-24
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-12-27 deposited with the CCDC.	2023-04-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 122.108(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.147(3)
_cell_length_b                   19.542(3)
_cell_length_c                   12.709(2)
_cell_measurement_reflns_used    5585
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      24.32
_cell_measurement_theta_min      2.273
_cell_volume                     4448.7(12)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      299.00
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0743
_diffrn_reflns_av_unetI/netI     0.0697
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 0.9980
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            49315
_diffrn_reflns_point_group_measured_fraction_full 1.0000
_diffrn_reflns_point_group_measured_fraction_max 0.9980
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         1.54
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0988 before and 0.0556 after correction.
The Ratio of minimum to maximum transmission is 0.9038.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.143
_exptl_crystal_description       block
_exptl_crystal_F_000             1652.844
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.8537
_refine_diff_density_min         -0.4691
_refine_diff_density_rms         0.0977
_refine_ls_d_res_high            0.7481
_refine_ls_d_res_low             13.2047
_refine_ls_goodness_of_fit_ref   1.0410
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    49
_refine_ls_number_parameters     279
_refine_ls_number_reflns         5549
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0410
_refine_ls_R_factor_all          0.1881
_refine_ls_R_factor_gt           0.0998
_refine_ls_shift/su_max          -0.0010
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1641P)^2^+3.6224P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2815
_refine_ls_wR_factor_ref         0.3430
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              23
_reflns_limit_h_min              -28
_reflns_limit_k_max              26
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                2562
_reflns_number_total             5549
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3cc00200d2.cif
_cod_data_source_block           BICAACRADICAL_0m_a
_cod_depositor_comments
'Adding full bibliography for 7131511--7131512.cif.'
_cod_database_code               7131511
_olex2_refinement_description
;
1. Others
 Fixed Sof: F4(0.5) F3(0.33333) F5(0.33333) F6(0.33333)
2.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20a,H20b), C16(H16a,H16b), C19(H19a,H19b)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C4(H4)
2.d Idealised Me refined as rotating group:
 C21(H21a,H21b,H21c), C22(H22a,H22b,H22c), C9(H9a,H9b,H9c), C12(H12a,H12b,
 H12c), C11(H11a,H11b,H11c), C8(H8a,H8b,H8c), C23(H23a,H23b,H23c)
;
_olex2_submission_special_instructions 'No special instructions were received'