An air-persistent oxyallyl radical cation with simple di(methyl)amino substituents.
Regnier, Vianney; Molton, Florian; Philouze, Christian; Martin, David; Chemical communications (Cambridge, England) 52 (2016) 11422–11425; doi:10.1039/c6cc06260a

data_7125034
_publ_section_title
;
 An air-persistent oxyallyl radical cation with simple di(methyl)amino
 substituents.
;
_journal_issue                   76
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11422
_journal_page_last               11425
_journal_paper_doi               10.1039/c6cc06260a
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'F6 P, C5.5 H12 N2 O0.5'
_chemical_formula_sum            'C5.5 H12 F6 N2 O0.5 P'
_chemical_formula_weight         259.14
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-06-23
_audit_creation_method
;
  Olex2 1.1
  (compiled Sep 28 2011 20:36:17, GUI svn.r3906)
;
_audit_update_record
;
2016-07-26 deposited with the CCDC.
2016-08-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 109.09(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.155(3)
_cell_length_b                   6.7318(13)
_cell_length_c                   19.587(4)
_cell_measurement_reflns_used    22857
_cell_measurement_temperature    200.0
_cell_measurement_theta_max      30.02
_cell_measurement_theta_min      3.31
_cell_volume                     2013.0(8)
_computing_cell_refinement       EvalCCD
_computing_data_collection       Collect
_computing_data_reduction        EvalCCD
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200.0
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'APEX II'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker-AXS-enraf-nonius KappaAPEXII'
_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  0.0647
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            22857
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.017
_diffrn_reflns_theta_min         3.307
_diffrn_source                   'Incoatec ISG250'
_diffrn_source_target            Mo
_diffrn_source_type              'Microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.336
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.642018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.1192 before and 0.0806 after correction.
The Ratio of minimum to maximum transmission is 0.6420.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.710
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2935
_refine_ls_number_restraints     186
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0556
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0725P)^2^+3.7103P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1491
_refine_ls_wR_factor_ref         0.1557
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2623
_reflns_number_total             2935
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc06260a2.cif
_cod_data_source_block           nany
_cod_original_cell_volume        2013.0(7)
_cod_original_formula_sum        'C5.50 H12 F6 N2 O0.50 P'
_cod_database_code               7125034
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 P1, F2B, F1, F4A, F5A, F3B, F1A, F2A, F4B, F5B, F2, F3A, F1B
 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 F2B \\sim F1 \\sim F4A \\sim F5A \\sim F3B \\sim F1A \\sim F2A \\sim
F4B \\sim F5B \\sim F2 \\sim F3A \\sim F1B: within 1.7A with sigma of 0.04 and
sigma for terminal atoms of 0.08
4. Others
 Sof(F3B)=Sof(F1B)=Sof(F4B)=Sof(F2B)=Sof(F1)=Sof(F5B)=1-FVAR(1)
 Sof(F2)=Sof(F1A)=Sof(F2A)=Sof(F4A)=Sof(F3A)=Sof(F5A)=FVAR(1)
5.a Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C3(H3A,H3B,H3C), C5(H5A,H5B,H5C), C4(H4A,H4B,H4C)
;
_shelx_res_checksum              82956
_shelx_hkl_checksum              93572
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'