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_1554850
_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         '2(F6 P), C16 H23 N3 O2'
_chemical_formula_sum            'C16 H23 F12 N3 O2 P2'
_chemical_formula_weight         579.31
_chemical_name_common            6a
_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   difmap
_audit_creation_date             2017-11-13
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2019-02-21 deposited with the CCDC.	2019-03-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.985(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5891(2)
_cell_length_b                   16.2883(4)
_cell_length_c                   13.9030(3)
_cell_measurement_reflns_used    9242
_cell_measurement_temperature    150.00(14)
_cell_measurement_theta_max      28.0140
_cell_measurement_theta_min      2.3170
_cell_volume                     2336.65(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9653
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -43.00  47.00   1.00   60.00    --   25.56 -57.00 -90.00   90
  2  \w    -25.00  67.00   1.00   60.00    --   25.56 -99.00-150.00   92
  3  \w    -25.00  67.00   1.00   60.00    --   25.56 -99.00  30.00   92
  4  \w    -47.00  51.00   1.00   60.00    --   25.56 -37.00  60.00   98
  5  \w    -97.00   3.00   1.00   60.00    --  -26.97 -77.00 150.00  100
  6  \w    -96.00  -6.00   1.00   60.00    --  -26.97 -57.00-150.00   90
  7  \w    -96.00  -6.00   1.00   60.00    --  -26.97 -57.00 -60.00   90
  8  \w    -97.00   3.00   1.00   60.00    --  -26.97 -77.00  60.00  100
  9  \w     -4.00  96.00   1.00   60.00    --   25.56  77.00 -30.00  100
 10  \w    -25.00  53.00   1.00   60.00    --   25.56 -99.00 -90.00   78
 11  \w   -104.00 -32.00   1.00   60.00    --  -26.97 178.00   0.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0343171000
_diffrn_orient_matrix_UB_12      0.0103509000
_diffrn_orient_matrix_UB_13      -0.0483756000
_diffrn_orient_matrix_UB_21      0.0553733000
_diffrn_orient_matrix_UB_22      0.0209931000
_diffrn_orient_matrix_UB_23      -0.0081229000
_diffrn_orient_matrix_UB_31      0.0219876000
_diffrn_orient_matrix_UB_32      -0.0367179000
_diffrn_orient_matrix_UB_33      -0.0182809000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            55687
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.508
_diffrn_reflns_theta_min         1.955
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93163
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent intense yellow'
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.321
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_min          0.133
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     463
_refine_ls_number_reflns         7121
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0530
_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^)+(0.0466P)^2^+1.4518P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1245
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5022
_reflns_number_total             7121
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00298g2.cif
_cod_data_source_block           6a
_cod_original_cell_volume        2336.64(9)
_cod_database_code               1554850
_chemical_oxdiff_formula         'P2 F12 O5 N3 C15 H20'
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_olex2_refinement_description
;
1. Uiso/Uaniso restraints and constraints
Uanis(F5A) \\sim Ueq, Uanis(F6A) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F3)
\\sim Ueq, Uanis(F3A) \\sim Ueq, Uanis(F4A) \\sim Ueq, Uanis(F2) \\sim Ueq,
Uanis(F6) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F1A) \\sim Ueq, Uanis(F4) \\sim
Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(F2A) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
2. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(F4A)=Sof(F5A)=Sof(F6A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
;
_shelx_shelxl_version_number     2016/6
_olex2_date_sample_data_collection 2017-11-10
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.105
_oxdiff_exptl_absorpt_empirical_full_min 0.936