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_7133447
_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         'Cl1, C50 H60 N4 O2, C H2 Cl2'
_chemical_formula_sum            'C51 H62 Cl3 N4 O2'
_chemical_formula_weight         869.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_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                 97.33(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.837(2)
_cell_length_b                   21.536(4)
_cell_length_c                   22.074(4)
_cell_measurement_reflns_used    10632
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      28.201
_cell_measurement_theta_min      1.326
_cell_volume                     5109.7(17)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.845
_diffrn_measurement_device_type  Synchrotron
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.70000
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.845
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            20010
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.201
_diffrn_reflns_theta_min         1.326
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.130
_exptl_crystal_description       block
_exptl_crystal_F_000             1852
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.021
_refine_diff_density_min         -0.923
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     593
_refine_ls_number_reflns         10632
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.141
_refine_ls_R_factor_all          0.1447
_refine_ls_R_factor_gt           0.0999
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2906
_refine_ls_wR_factor_ref         0.3294
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6068
_reflns_number_total             10632
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02092h2.cif
_cod_data_source_block           p21n
_cod_original_cell_volume        5109.7(18)
_cod_database_code               7133447
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.978
_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. Restrained distances
 Cl3-C51 \\sim Cl4-C52
 with sigma of 0.02
 C51-Cl5 \\sim C52-Cl6
 with sigma of 0.02
 Cl3-Cl5 \\sim Cl4-Cl6
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C52) \\sim Ueq: with sigma of 0.03 and sigma for terminal atoms of 0.06
4. Others
 Sof(Cl6)=Sof(C52)=Sof(H53A)=Sof(H53B)=Sof(Cl4)=1-FVAR(1)
 Sof(Cl3)=Sof(C51)=Sof(H52A)=Sof(H52B)=Sof(Cl5)=FVAR(1)
 Sof(Cl1)=1-FVAR(2)
 Sof(Cl2)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C30(H18), C27(H15), C18(H31), C15(H28)
5.b Secondary CH2 refined with riding coordinates:
 C51(H52A,H52B), C52(H53A,H53B)
5.c Aromatic/amide H refined with riding coordinates:
 C5(H4), C6(H5), C37(H45), C35(H47), C7(H7), C8(H8), C44(H38), C25(H13),
 C46(H36), C23(H11), C24(H12), C13(H25), C12(H24), C11(H23)
5.d Idealised Me refined as rotating group:
 C39(H49A,H49B,H49C), C50(H41A,H41B,H41C), C41(H51A,H51B,H51C), C40(H50A,H50B,
 H50C), C32(H20A,H20B,H20C), C29(H16A,H16B,H16C), C48(H40A,H40B,H40C), C28(H17A,
 H17B,H17C), C16(H29A,H29B,H29C), C31(H19A,H19B,H19C), C49(H42A,H42B,H42C),
 C19(H32A,H32B,H32C), C20(H33A,H33B,H33C), C17(H30A,H30B,H30C)
;
_shelx_res_checksum              50909
_shelx_hkl_checksum              37197
_olex2_submission_special_instructions 'No special instructions were received'