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_1554849
_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 N3 O2, F6 P, C2 H3 N'
_chemical_formula_sum            'C21 H32 F6 N4 O2 P'
_chemical_formula_weight         517.47
_chemical_name_common            9b
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_date             2018-01-19
_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                 113.783(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3903(10)
_cell_length_b                   16.1931(10)
_cell_length_c                   13.6174(11)
_cell_measurement_reflns_used    3156
_cell_measurement_temperature    149.95(10)
_cell_measurement_theta_max      28.2540
_cell_measurement_theta_min      2.9970
_cell_volume                     2500.1(4)
_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 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  41.00   1.00   10.00    --   -0.62 -99.00  60.00   66
  2  \w     34.00 125.00   1.00   60.00    --   55.51  52.00  23.00   91
  3  \w     25.00 126.00   1.00   60.00    --   55.51  77.00 120.00  101
  4  \w    -13.00  77.00   1.00   60.00    --   55.51 -57.00  60.00   90
  5  \w     73.00 127.00   1.00   60.00    --   55.51 125.00 -60.00   54
  6  \w     73.00 127.00   1.00   60.00    --   55.51 125.00  60.00   54
  7  \w     25.00 126.00   1.00   60.00    --   55.51  77.00  60.00  101
  8  \w    -15.00  86.00   1.00   60.00    --   55.51 -77.00-120.00  101
  9  \w   -129.00-117.00   1.00   60.00    --  -56.76 -99.00   0.00   12
;
_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      -0.0060584000
_diffrn_orient_matrix_UB_12      -0.0182482000
_diffrn_orient_matrix_UB_13      0.0448381000
_diffrn_orient_matrix_UB_21      0.0511865000
_diffrn_orient_matrix_UB_22      0.0211952000
_diffrn_orient_matrix_UB_23      0.0349698000
_diffrn_orient_matrix_UB_31      -0.0354947000
_diffrn_orient_matrix_UB_32      0.0337049000
_diffrn_orient_matrix_UB_33      0.0022994000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23721
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.062
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.968
_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    1.375
_exptl_crystal_description       needle
_exptl_crystal_F_000             1084
_exptl_crystal_size_max          0.722
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.081
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     490
_refine_ls_number_reflns         5052
_refine_ls_number_restraints     66
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0580
_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^)+(0.0572P)^2^+1.8405P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1473
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3569
_reflns_number_total             5052
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00298g2.cif
_cod_data_source_block           9b
_cod_original_cell_volume        2500.2(4)
_cod_database_code               1554849
_chemical_oxdiff_formula         'Cl O2 N3 P F6 C20 H40'
_reflns_odcompleteness_completeness 98.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_olex2_refinement_description
;
1. Uiso/Uaniso restraints and constraints
F1 \\sim F4 \\sim F5 \\sim F3 \\sim F2 \\sim F6 \\sim F6B \\sim F2B \\sim F5B
\\sim F3B \\sim F4B: within 1.7A with sigma of 0.01 and sigma for terminal
atoms of 0.01
Uanis(P1) \\sim Ueq, Uanis(P1B) \\sim Ueq: with sigma of 0.002 and sigma for
terminal atoms of 0.004
2. Others
 Sof(P1B)=Sof(F2B)=Sof(F3B)=Sof(F4B)=Sof(F5B)=Sof(F6B)=1-FVAR(1)
 Sof(P1)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
;
_shelx_shelxl_version_number     2016/6
_olex2_date_sample_data_collection 2018-01-18
_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 1.253
_oxdiff_exptl_absorpt_empirical_full_min 0.855