#------------------------------------------------------------------------------
#$Date: 2019-11-23 18:31:42 +0200 (Sat, 23 Nov 2019) $
#$Revision: 234444 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/50/7125034.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7125034
loop_
_publ_author_name
'Regnier, Vianney'
'Molton, Florian'
'Philouze, Christian'
'Martin, David'
_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 λ/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/[σ²(Fo²)+(0.0725P)²+3.7103P] where P=(Fo²+2Fc²)/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
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.33600(3) 0.16291(8) 0.39342(3) 0.03479(17) Uani 1 1 d U . .
N2 N 0.48997(9) 0.5577(2) 0.32878(7) 0.0248(3) Uani 1 1 d . . .
O1 O 0.5000 0.1019(3) 0.2500 0.0370(4) Uani 1 2 d S . .
F3B F 0.2941(5) -0.0309(9) 0.3534(5) 0.099(2) Uani 0.385(5) 1 d PU A 2
N1 N 0.59759(9) 0.3123(2) 0.37339(7) 0.0269(3) Uani 1 1 d . . .
C6 C 0.40009(11) 0.6039(3) 0.28231(10) 0.0309(3) Uani 1 1 d . . .
H6A H 0.4013 0.7134 0.2513 0.046 Uiso 1 1 calc R . .
H6B H 0.3652 0.6386 0.3119 0.046 Uiso 1 1 calc R . .
H6C H 0.3752 0.4898 0.2535 0.046 Uiso 1 1 calc R . .
C1 C 0.53131(10) 0.3928(2) 0.32217(8) 0.0221(3) Uani 1 1 d . . .
C2 C 0.5000 0.2802(3) 0.2500 0.0234(4) Uani 1 2 d S . .
F1B F 0.2676(4) 0.2894(11) 0.3254(4) 0.115(3) Uani 0.385(5) 1 d PU A 2
C3 C 0.66091(12) 0.1728(3) 0.35979(12) 0.0373(4) Uani 1 1 d . . .
H3A H 0.6499 0.0412 0.3736 0.056 Uiso 1 1 calc R . .
H3B H 0.7193 0.2122 0.3876 0.056 Uiso 1 1 calc R . .
H3C H 0.6547 0.1744 0.3093 0.056 Uiso 1 1 calc R . .
C5 C 0.52777(15) 0.7123(3) 0.38296(11) 0.0384(4) Uani 1 1 d . . .
H5A H 0.5122 0.8409 0.3614 0.058 Uiso 1 1 calc R . .
H5B H 0.5904 0.6992 0.4004 0.058 Uiso 1 1 calc R . .
H5C H 0.5054 0.6978 0.4225 0.058 Uiso 1 1 calc R . .
C4 C 0.61442(16) 0.3484(3) 0.45091(10) 0.0437(5) Uani 1 1 d . . .
H4A H 0.6618 0.4413 0.4684 0.066 Uiso 1 1 calc R . .
H4B H 0.6298 0.2256 0.4769 0.066 Uiso 1 1 calc R . .
H4C H 0.5627 0.4019 0.4579 0.066 Uiso 1 1 calc R . .
F4B F 0.3980(5) 0.1635(9) 0.3443(5) 0.078(2) Uani 0.385(5) 1 d PU A 2
F2B F 0.4017(6) 0.0606(11) 0.4504(4) 0.121(3) Uani 0.385(5) 1 d PU A 2
F1 F 0.2737(9) 0.1828(13) 0.4357(8) 0.161(5) Uani 0.385(5) 1 d PU A 2
F5B F 0.3775(5) 0.3797(12) 0.4187(4) 0.0649(18) Uani 0.385(5) 1 d PU A 2
F2 F 0.3342(3) 0.1336(5) 0.47524(14) 0.0739(12) Uani 0.615(5) 1 d PU A 1
F1A F 0.23418(18) 0.1481(6) 0.3695(2) 0.0846(13) Uani 0.615(5) 1 d PU A 1
F2A F 0.4396(2) 0.1636(7) 0.4252(4) 0.123(2) Uani 0.615(5) 1 d PU A 1
F4A F 0.3415(5) 0.1799(7) 0.3181(2) 0.118(2) Uani 0.615(5) 1 d PU A 1
F3A F 0.3404(3) -0.0784(4) 0.3903(2) 0.0628(9) Uani 0.615(5) 1 d PU A 1
F5A F 0.3337(3) 0.3909(6) 0.4044(3) 0.0728(13) Uani 0.615(5) 1 d PU A 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_3
F3B P1 F1B 87.7(4) .
F3B P1 F4B 87.4(4) .
F3B P1 F5B 168.4(4) .
F4B P1 F1B 84.2(4) .
F4B P1 F5B 84.5(4) .
F2B P1 F3B 94.5(5) .
F2B P1 F1B 174.8(5) .
F2B P1 F4B 91.1(5) .
F2B P1 F1 94.1(7) .
F2B P1 F5B 93.9(4) .
F1 P1 F3B 95.3(5) .
F1 P1 F1B 90.4(7) .
F1 P1 F4B 173.9(5) .
F1 P1 F5B 92.1(5) .
F5B P1 F1B 83.3(4) .
F2 P1 F3A 86.02(18) .
F1A P1 F2 86.0(2) .
F1A P1 F2A 173.6(3) .
F1A P1 F3A 88.82(19) .
F2A P1 F2 88.3(3) .
F2A P1 F3A 88.0(2) .
F4A P1 F2 176.6(3) .
F4A P1 F1A 96.0(4) .
F4A P1 F2A 89.6(4) .
F4A P1 F3A 91.3(2) .
F4A P1 F5A 94.1(3) .
F5A P1 F2 88.5(2) .
F5A P1 F1A 92.0(2) .
F5A P1 F2A 90.7(3) .
F5A P1 F3A 174.4(2) .
C1 N2 C6 122.93(14) .
C1 N2 C5 124.11(15) .
C5 N2 C6 112.95(15) .
C1 N1 C3 124.18(15) .
C1 N1 C4 123.08(16) .
C4 N1 C3 112.72(16) .
N2 C6 H6A 109.5 .
N2 C6 H6B 109.5 .
N2 C6 H6C 109.5 .
H6A C6 H6B 109.5 .
H6A C6 H6C 109.5 .
H6B C6 H6C 109.5 .
N2 C1 C2 118.61(13) .
N1 C1 N2 125.43(14) .
N1 C1 C2 115.94(14) .
O1 C2 C1 119.55(9) 2_655
O1 C2 C1 119.56(9) .
C1 C2 C1 120.89(19) 2_655
N1 C3 H3A 109.5 .
N1 C3 H3B 109.5 .
N1 C3 H3C 109.5 .
H3A C3 H3B 109.5 .
H3A C3 H3C 109.5 .
H3B C3 H3C 109.5 .
N2 C5 H5A 109.5 .
N2 C5 H5B 109.5 .
N2 C5 H5C 109.5 .
H5A C5 H5B 109.5 .
H5A C5 H5C 109.5 .
H5B C5 H5C 109.5 .
N1 C4 H4A 109.5 .
N1 C4 H4B 109.5 .
N1 C4 H4C 109.5 .
H4A C4 H4B 109.5 .
H4A C4 H4C 109.5 .
H4B C4 H4C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 F3B 1.559(5) .
P1 F1B 1.661(6) .
P1 F4B 1.599(5) .
P1 F2B 1.440(6) .
P1 F1 1.505(5) .
P1 F5B 1.615(7) .
P1 F2 1.625(3) .
P1 F1A 1.559(3) .
P1 F2A 1.584(3) .
P1 F4A 1.510(3) .
P1 F3A 1.628(3) .
P1 F5A 1.552(4) .
N2 C6 1.473(2) .
N2 C1 1.324(2) .
N2 C5 1.469(2) .
O1 C2 1.201(3) .
N1 C1 1.321(2) .
N1 C3 1.475(2) .
N1 C4 1.473(2) .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
C1 C2 1.5366(19) .
C2 C1 1.5366(19) 2_655
C3 H3A 0.9600 .
C3 H3B 0.9600 .
C3 H3C 0.9600 .
C5 H5A 0.9600 .
C5 H5B 0.9600 .
C5 H5C 0.9600 .
C4 H4A 0.9600 .
C4 H4B 0.9600 .
C4 H4C 0.9600 .
