Stable dicationic dioxoliums and fate of their dioxolyl radicals
Devillard, Marc; Regnier, Vianney; Pecaut, Jacques; Martin, David; Organic Chemistry Frontiers 6 (2019) 3184–; doi:10.1039/C9QO00298G

data_1554845
_publ_section_title
;
 Stable dicationic dioxoliums and fate of their dioxolyl radicals
;
_journal_issue                   18
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3184
_journal_paper_doi               10.1039/C9QO00298G
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'F6 P, C28 H41 N4 O2'
_chemical_formula_sum            'C28 H41 F6 N4 O2 P'
_chemical_formula_weight         610.62
_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   geom
_audit_creation_date             2017-09-22
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_audit_update_record
;
2019-02-21 deposited with the CCDC.	2019-03-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.44(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   36.485(7)
_cell_length_b                   10.158(2)
_cell_length_c                   16.856(3)
_cell_measurement_reflns_used    39100
_cell_measurement_temperature    200
_cell_measurement_theta_max      30.000
_cell_measurement_theta_min      1.117
_cell_volume                     6241(2)
_computing_cell_refinement       EvalCCD
_computing_data_collection       Collect
_computing_data_reduction        EvalCCD
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'APEX II'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  Incoatec-Bruker-AXS-enraf-noniusKappaAPEXII
_diffrn_measurement_method       'Phi and omega scans'
_diffrn_radiation_collimation    'Montel optic'
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Multilayer mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       51
_diffrn_reflns_limit_h_min       -51
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            39100
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         1.117
_diffrn_source                   'Incoatec ISG250'
_diffrn_source_target            Mo
_diffrn_source_type              'Microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.829179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.1572 before and 0.0431 after correction.
The Ratio of minimum to maximum transmission is 0.8292.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_description       block
_exptl_crystal_F_000             2576
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     438
_refine_ls_number_reflns         9050
_refine_ls_number_restraints     165
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0524
_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^)+(0.0481P)^2^+6.5955P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1496
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6317
_reflns_number_total             9050
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00298g2.cif
_cod_data_source_block           5
_cod_original_cell_volume        6242(2)
_cod_database_code               1554845
_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. Rigid bond restraints
 P1, F9, F1, F3, F10, F5, F4, F2, F7, F6, F8
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C22B, C22A, C1E, C1FB, C1FA
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
P1 \\sim F9 \\sim F1 \\sim F3 \\sim F10 \\sim F5 \\sim F4 \\sim F2 \\sim F7
\\sim F6 \\sim F8: within 1.7A with sigma of 0.04 and sigma for terminal atoms
of 0.08
C22B \\sim C22A \\sim C1E \\sim C1FB \\sim C1FA: within 1.7A with sigma of 0.04
and sigma for terminal atoms of 0.08
4. Others
 Sof(F6)=Sof(F8)=Sof(F9)=Sof(F10)=1-FVAR(1)
 Sof(F3)=Sof(F1)=Sof(F5)=Sof(F7)=FVAR(1)
 Sof(H1EA)=Sof(C1FB)=Sof(H1FA)=Sof(H1FB)=Sof(H1FC)=Sof(C22B)=Sof(H22A)=
 Sof(H22B)=Sof(H22C)=1-FVAR(2)
 Sof(H1E)=Sof(C22A)=Sof(H22D)=Sof(H22E)=Sof(H22F)=Sof(C1FA)=Sof(H1FD)=
 Sof(H1FE)=Sof(H1FF)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C2(H2), C17(H17), C1E(H1EA), C1E(H1E)
5.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C14(H14), C15(H15), C16(H16), C1A(H1A), C1B(H1B), C1C(H1C), C1D(H1D)
5.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C1FB(H1FA,H1FB,H1FC),
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22B(H22A,H22B,H22C), C22A(H22D,H22E,
 H22F), C1FA(H1FD,H1FE,H1FF)
;
_shelx_res_checksum              9299
_shelx_hkl_checksum              90530
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'