Synthesis of sterically congested unsymmetrical 1,2-dicarbonyl radicals through a stepwise approach.
Song, Yuna; Song, Hayoung; Choi, Yunseop; Seo, Jongcheol; Lee, Eunsung; Chemical communications (Cambridge, England) 60 (2024) 8043–8046; doi:10.1039/d4cc02092h

data_7133450
_publ_section_title
;
 Synthesis of sterically congested unsymmetrical 1,2-dicarbonyl radicals
 through a stepwise approach.
;
_journal_issue                   62
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8043
_journal_page_last               8046
_journal_paper_doi               10.1039/d4cc02092h
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'Cl, H2 O, C51 H64 N4 O2'
_chemical_formula_sum            'C51 H66 Cl N4 O3'
_chemical_formula_weight         818.52
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-12-03
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6392)
;
_audit_update_record
;
2024-04-24 deposited with the CCDC.	2024-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 122.41(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.135(5)
_cell_length_b                   22.011(4)
_cell_length_c                   21.701(4)
_cell_measurement_reflns_used    24582
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.514
_cell_measurement_theta_min      1.850
_cell_volume                     9733(5)
_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      100
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.719
_diffrn_measurement_device_type  Synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.700000
_diffrn_reflns_av_R_equivalents  0.0838
_diffrn_reflns_av_unetI/netI     0.0923
_diffrn_reflns_Laue_measured_fraction_full 0.952
_diffrn_reflns_Laue_measured_fraction_max 0.719
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            24582
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.719
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.514
_diffrn_reflns_theta_min         1.850
_exptl_absorpt_coefficient_mu    0.122
_exptl_crystal_colour            'clear dark violet'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.117
_exptl_crystal_description       block
_exptl_crystal_F_000             3528
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.630
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     549
_refine_ls_number_reflns         8888
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.950
_refine_ls_R_factor_all          0.1132
_refine_ls_R_factor_gt           0.0597
_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^)+(0.0753P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1462
_refine_ls_wR_factor_ref         0.1668
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4732
_reflns_number_total             8888
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02092h2.cif
_cod_data_source_block           monoclinic-c2c
_cod_original_cell_volume        9733(4)
_cod_database_code               7133450
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.964
_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, All O(H,H) groups
2.a Free rotating group:
 O3(H3A,H3B)
2.b Ternary CH refined with riding coordinates:
 C17(H17), C20(H20), C32(H32), C29(H29)
2.c Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B)
2.d Aromatic/amide H refined with riding coordinates:
 C14(H14), C12(H12), C13(H13), C9(H9), C27(H27), C8(H8), C25(H25), C39(H39),
 C26(H26), C46(H46), C37(H37), C48(H48)
2.e Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C), C30(H30A,H30B,H30C), C41(H41A,H41B,H41C), C51(H51A,H51B,H51C), C42(H42A,
 H42B,H42C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C43(H43A,H43B,H43C),
 C31(H31A,H31B,H31C), C50(H50A,H50B,H50C), C52(H52A,H52B,H52C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'