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_7133449
_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, C37 H52 N4 O2, H2 O'
_chemical_formula_sum            'C37 H54 Cl N4 O3'
_chemical_formula_weight         638.29
_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   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                87.59(3)
_cell_angle_beta                 88.68(3)
_cell_angle_gamma                81.55(3)
_cell_formula_units_Z            4
_cell_length_a                   11.704(2)
_cell_length_b                   16.986(3)
_cell_length_c                   19.521(4)
_cell_measurement_reflns_used    36993
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.344
_cell_measurement_theta_min      1.631
_cell_volume                     3834.8(13)
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_device_type  Synchrotron
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.700000
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_unetI/netI     0.0974
_diffrn_reflns_Laue_measured_fraction_full 0.941
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            36993
_diffrn_reflns_point_group_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.344
_diffrn_reflns_theta_min         1.631
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.106
_exptl_crystal_description       block
_exptl_crystal_F_000             1380
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.052
_refine_diff_density_min         -0.807
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     859
_refine_ls_number_reflns         21048
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.1329
_refine_ls_R_factor_gt           0.0733
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0972P)^2^+0.1670P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1830
_refine_ls_wR_factor_ref         0.2081
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11603
_reflns_number_total             21048
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02092h2.cif
_cod_data_source_block           p-1
_cod_original_cell_volume        3834.8(14)
_cod_database_code               7133449
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.973
_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. Others
 Fixed Sof: C76(0.8) C77(0.8) C39(0.2) C40(0.2)
3.a Free rotating group:
 O5(H5A,H5B), O6(H6A,H6B)
3.b Ternary CH refined with riding coordinates:
 C54(H54), C51(H51), C64(H64), C32(H32), C35(H35), C23(H23), C67(H67), C20(H20)
3.c Secondary CH2 refined with riding coordinates:
 C43(H43A,H43B), C42(H42A,H42B), C44(H44A,H44B), C11(H11A,H11B), C13(H13A,
 H13B), C12(H12A,H12B)
3.d Aromatic/amide H refined with riding coordinates:
 C47(H47), C49(H49), C48(H48), C28(H28), C30(H30), C16(H16), C29(H29),
 C17(H17), C62(H62), C18(H18), C60(H60), C61(H61)
3.e Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C),
 C53(H53A,H53B,H53C), C37(H37A,H37B,H37C), C74(H74A,H74B,H74C), C73(H73A,H73B,
 H73C), C52(H52A,H52B,H52C), C33(H33A,H33B,H33C), C65(H65A,H65B,H65C), C55(H55A,
 H55B,H55C), C36(H36A,H36B,H36C), C56(H56A,H56B,H56C), C72(H72A,H72B,H72C),
 C75(H75A,H75B,H75C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C66(H66A,H66B,
 H66C), C21(H21A,H21B,H21C), C34(H34A,H34B,H34C), C68(H68A,H68B,H68C), C69(H69A,
 H69B,H69C), C25(H25A,H25B,H25C)
;
_shelx_res_checksum              13395
_shelx_hkl_checksum              73884
_shelx_fab_checksum              89386
_olex2_submission_special_instructions 'No special instructions were received'