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_1554848
_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         'C19 H29 Cl N3 O2, F6 P'
_chemical_formula_sum            'C19 H29 Cl F6 N3 O2 P'
_chemical_formula_weight         511.87
_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             2018-01-18
_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                 107.133(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.59057(19)
_cell_length_b                   26.3895(7)
_cell_length_c                   12.4880(3)
_cell_measurement_reflns_used    5838
_cell_measurement_temperature    149.95(10)
_cell_measurement_theta_max      31.6930
_cell_measurement_theta_min      2.8430
_cell_volume                     2390.48(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (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      149.95(10)
_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    -25.00  74.00   1.00   30.00    --   25.72   0.00  60.00   99
  2  \w   -102.00 -61.00   1.00   30.00    --  -27.28-178.00 120.00   41
  3  \w      4.00  67.00   1.00   30.00    --   25.41 -99.00  90.00   63
  4  \w    -25.00   1.00   1.00   30.00    --   25.41 -99.00  90.00   26
  5  \w    -97.00 -72.00   1.00   30.00    --  -26.97 -77.00 150.00   25
  6  \w     -8.00  86.00   1.00   30.00    --   25.41  19.00 120.00   94
  7  \w   -104.00 -76.00   1.00   30.00    --  -26.97 178.00-120.00   28
  8  \w    -87.00 -10.00   1.00   30.00    --  -26.97 129.00 136.00   77
  9  \w    -97.00 -53.00   1.00   30.00    --  -26.97 -77.00-150.00   44
;
_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      -0.0954253000
_diffrn_orient_matrix_UB_12      0.0049202000
_diffrn_orient_matrix_UB_13      -0.0237899000
_diffrn_orient_matrix_UB_21      -0.0182289000
_diffrn_orient_matrix_UB_22      -0.0264012000
_diffrn_orient_matrix_UB_23      -0.0023716000
_diffrn_orient_matrix_UB_31      -0.0110246000
_diffrn_orient_matrix_UB_32      0.0010100000
_diffrn_orient_matrix_UB_33      0.0544348000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            28619
_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         30.505
_diffrn_reflns_theta_min         2.301
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.294
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.992
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_description       needle
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.774
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.073
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         7291
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0449
_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^)+(0.0410P)^2^+1.1724P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1058
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5933
_reflns_number_total             7291
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00298g2.cif
_cod_data_source_block           1b
_cod_original_cell_volume        2390.47(11)
_cod_database_code               1554848
_chemical_oxdiff_formula         C19H29ClF6N3O2P
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_olex2_refinement_description
;
1. Uiso/Uaniso restraints and constraints
Uanis(F5B) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F4B) \\sim Ueq, Uanis(F4)
\\sim Ueq, Uanis(F3B) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F6B) \\sim Ueq,
Uanis(F6) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
2. Others
 Sof(F3B)=Sof(F4B)=Sof(F6B)=Sof(F5B)=1-FVAR(1)
 Sof(F5)=Sof(F3)=Sof(F4)=Sof(F6)=FVAR(1)
;
_shelx_shelxl_version_number     2016/6
_olex2_date_sample_data_collection 2018-01-17
_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 1.103
_oxdiff_exptl_absorpt_empirical_full_min 0.884