#------------------------------------------------------------------------------
#$Date: 2020-03-10 01:39:55 +0200 (Tue, 10 Mar 2020) $
#$Revision: 249207 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/43/4134369.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_4134369
loop_
_publ_author_name
'Gosset, Alexis'
'Wilbraham, Liam'
'Lachmanova, Stepanka Novakova'
'Sokolova, Romana'
'Dupeyre, Grégory'
'Tuyèras, Fabien'
'Ochsenbein, Philippe'
'Perruchot, Christian'
'Jacquot de Rouville, Henri-Pierre'
'Randriamahazaka, Hyacinthe'
'Pospisil, Lubomir'
'Ciofini, Ilaria'
'Hromadová, Magdaléna'
'Lainé, Philippe P'
_publ_section_title
;
 Electron Storage System Based on a Two-Way Inversion of Redox Potentials.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b12762
_journal_year                    2020
_chemical_compound_source        'see text'
_chemical_formula_moiety         '(C22 H18 N), (F6 P)'
_chemical_formula_sum            'C22 H18 F6 N P'
_chemical_formula_weight         441.35
_chemical_name_common
'1-phenyl-8-(N-methylpyrid-4-ylium)naphthalene hexafluorophosphate'
_chemical_name_systematic
'1-phenyl-8-(N-methylpyrid-4-ylium)naphthalene hexafluorophosphate'
_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   geom
_audit_creation_date             'Aug 14 15:19:25 2016'
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 99.9723(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6866(5)
_cell_length_b                   8.5079(4)
_cell_length_c                   18.5222(8)
_cell_measurement_reflns_used    344
_cell_measurement_temperature    113(1)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      4.5
_cell_volume                     1969.01(15)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'SHELXP-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      113(1)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Instrument Service v2011.8.1.0'
_diffrn_measurement_method       'π and ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            66719
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.410
_diffrn_reflns_theta_min         1.630
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_description       Block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.649
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.262
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         9607
_refine_ls_number_restraints     228
_refine_ls_restrained_S_all      1.247
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0532
_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/[σ²(Fo²)+(0.0600P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1439
_refine_ls_wR_factor_ref         0.1593
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7985
_reflns_number_total             9607
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja9b12762_si_002.cif
_cod_data_source_block           xea
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4134369
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.960
_shelx_estimated_absorpt_t_max   0.970
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.46602(2) 0.16742(3) 0.13753(2) 0.01933(7) Uani 1 1 d . U . . .
F1 F 0.42982(8) 0.05526(11) 0.19865(5) 0.03219(18) Uani 1 1 d . U . . .
N1 N 0.63571(7) 0.72584(12) 0.12825(5) 0.01883(15) Uani 1 1 d . U . . .
F2 F 0.58152(7) 0.08834(14) 0.15199(6) 0.0416(2) Uani 1 1 d . U . . .
C2 C 0.65726(9) 0.80919(15) 0.07082(6) 0.02174(19) Uani 1 1 d . U . . .
H2A H 0.6001 0.8433 0.0341 0.026 Uiso 1 1 calc R U . . .
F3 F 0.42558(8) 0.03443(10) 0.07716(4) 0.03212(18) Uani 1 1 d . U . . .
C3 C 0.76114(9) 0.84585(15) 0.06445(6) 0.0232(2) Uani 1 1 d . U . . .
H3A H 0.7749 0.9040 0.0233 0.028 Uiso 1 1 calc R U . . .
F4 F 0.49956(7) 0.27823(12) 0.07531(5) 0.03500(19) Uani 1 1 d . U . . .
C4 C 0.84654(8) 0.79790(13) 0.11834(6) 0.01903(17) Uani 1 1 d . U . . .
C5 C 0.82056(8) 0.71724(15) 0.17897(5) 0.02020(18) Uani 1 1 d . U . . .
H5A H 0.8758 0.6870 0.2179 0.024 Uiso 1 1 calc R U . . .
F5 F 0.34862(8) 0.24257(12) 0.12144(8) 0.0466(3) Uani 1 1 d . U . . .
C6 C 0.71566(8) 0.68151(14) 0.18258(6) 0.02063(18) Uani 1 1 d . U . . .
H6A H 0.6993 0.6253 0.2236 0.025 Uiso 1 1 calc R U . . .
F6 F 0.50532(12) 0.29763(13) 0.19755(6) 0.0538(3) Uani 1 1 d . U . . .
C7 C 0.52382(9) 0.68246(16) 0.13187(7) 0.0255(2) Uani 1 1 d . U . . .
H7A H 0.5216 0.5742 0.1496 0.038 Uiso 1 1 calc R U . . .
H7B H 0.4801 0.6908 0.0829 0.038 Uiso 1 1 calc R U . . .
H7C H 0.4956 0.7536 0.1655 0.038 Uiso 1 1 calc R U . . .
C8 C 0.95829(9) 0.84018(14) 0.11335(6) 0.02111(18) Uani 1 1 d . U . . .
C9 C 0.97452(11) 0.99446(16) 0.09441(9) 0.0301(2) Uani 1 1 d . U . . .
H9A H 0.9142 1.0590 0.0775 0.036 Uiso 1 1 calc R U . . .
C10 C 1.07802(13) 1.05883(18) 0.09941(10) 0.0358(3) Uani 1 1 d . U . . .
H10A H 1.0871 1.1634 0.0836 0.043 Uiso 1 1 calc R U . . .
C11 C 1.16490(11) 0.96973(19) 0.12716(9) 0.0327(3) Uani 1 1 d . U . . .
H11A H 1.2342 1.0156 0.1345 0.039 Uiso 1 1 calc R U . . .
C12 C 1.15309(9) 0.80905(16) 0.14527(7) 0.0246(2) Uani 1 1 d . U . . .
C13 C 1.24535(9) 0.7191(2) 0.17384(7) 0.0313(3) Uani 1 1 d . U . . .
H13A H 1.3135 0.7686 0.1832 0.038 Uiso 1 1 calc R U . . .
C14 C 1.23715(10) 0.5624(2) 0.18795(8) 0.0325(3) Uani 1 1 d . U . . .
H14A H 1.2985 0.5042 0.2095 0.039 Uiso 1 1 calc R U . . .
C15 C 1.13658(10) 0.48773(17) 0.17018(7) 0.0270(2) Uani 1 1 d . U . . .
H15A H 1.1322 0.3775 0.1773 0.032 Uiso 1 1 calc R U . . .
C16 C 1.04384(8) 0.57001(14) 0.14263(6) 0.01939(17) Uani 1 1 d . U . . .
C17 C 1.04927(8) 0.73748(14) 0.13387(6) 0.01930(17) Uani 1 1 d . U . . .
C18 C 0.94448(8) 0.47820(13) 0.11758(6) 0.01845(17) Uani 1 1 d . U . . .
C19 C 0.90530(10) 0.37222(16) 0.16446(7) 0.0260(2) Uani 1 1 d . U . . .
H19A H 0.9439 0.3557 0.2126 0.031 Uiso 1 1 calc R U . . .
C20 C 0.81021(11) 0.29080(17) 0.14117(9) 0.0316(3) Uani 1 1 d . U . . .
H20A H 0.7834 0.2214 0.1739 0.038 Uiso 1 1 calc R U . . .
C21 C 0.75449(11) 0.31049(18) 0.07049(9) 0.0322(3) Uani 1 1 d . U . . .
H21A H 0.6896 0.2549 0.0548 0.039 Uiso 1 1 calc R U . . .
C22 C 0.79392(9) 0.41211(17) 0.02254(7) 0.0271(2) Uani 1 1 d . U . . .
H22A H 0.7565 0.4246 -0.0262 0.033 Uiso 1 1 calc R U . . .
C23 C 0.88831(8) 0.49557(14) 0.04606(6) 0.02011(18) Uani 1 1 d . U . . .
H23A H 0.9147 0.5649 0.0132 0.024 Uiso 1 1 calc R U . . .
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'
N N 0.0061 0.0033 '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'
F F 0.0171 0.0103 '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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F6 P1 F2 90.50(7) . . ?
F6 P1 F5 91.20(7) . . ?
F2 P1 F5 178.29(7) . . ?
F6 P1 F4 90.16(6) . . ?
F2 P1 F4 91.06(5) . . ?
F5 P1 F4 89.17(6) . . ?
F6 P1 F1 90.83(6) . . ?
F2 P1 F1 89.86(5) . . ?
F5 P1 F1 89.89(6) . . ?
F4 P1 F1 178.65(5) . . ?
F6 P1 F3 179.46(6) . . ?
F2 P1 F3 89.61(6) . . ?
F5 P1 F3 88.69(6) . . ?
F4 P1 F3 90.37(5) . . ?
F1 P1 F3 88.64(5) . . ?
C2 N1 C6 120.41(9) . . ?
C2 N1 C7 119.69(9) . . ?
C6 N1 C7 119.90(9) . . ?
N1 C2 C3 120.99(10) . . ?
N1 C2 H2A 119.5 . . ?
C3 C2 H2A 119.5 . . ?
C2 C3 C4 120.39(10) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 H3A 119.8 . . ?
C3 C4 C5 116.92(9) . . ?
C3 C4 C8 121.04(10) . . ?
C5 C4 C8 121.92(10) . . ?
C6 C5 C4 120.62(10) . . ?
C6 C5 H5A 119.7 . . ?
C4 C5 H5A 119.7 . . ?
N1 C6 C5 120.56(10) . . ?
N1 C6 H6A 119.7 . . ?
C5 C6 H6A 119.7 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C17 119.55(10) . . ?
C9 C8 C4 115.63(10) . . ?
C17 C8 C4 124.50(10) . . ?
C8 C9 C10 121.97(13) . . ?
C8 C9 H9A 119.0 . . ?
C10 C9 H9A 119.0 . . ?
C11 C10 C9 119.44(14) . . ?
C11 C10 H10A 120.3 . . ?
C9 C10 H10A 120.3 . . ?
C10 C11 C12 120.83(12) . . ?
C10 C11 H11A 119.6 . . ?
C12 C11 H11A 119.6 . . ?
C13 C12 C11 119.45(12) . . ?
C13 C12 C17 120.18(12) . . ?
C11 C12 C17 120.37(12) . . ?
C14 C13 C12 120.76(12) . . ?
C14 C13 H13A 119.6 . . ?
C12 C13 H13A 119.6 . . ?
C13 C14 C15 119.33(12) . . ?
C13 C14 H14A 120.3 . . ?
C15 C14 H14A 120.3 . . ?
C16 C15 C14 122.22(13) . . ?
C16 C15 H15A 118.9 . . ?
C14 C15 H15A 118.9 . . ?
C15 C16 C17 119.17(11) . . ?
C15 C16 C18 117.93(11) . . ?
C17 C16 C18 122.70(9) . . ?
C12 C17 C16 117.74(10) . . ?
C12 C17 C8 116.98(11) . . ?
C16 C17 C8 125.27(9) . . ?
C23 C18 C19 118.52(10) . . ?
C23 C18 C16 120.34(9) . . ?
C19 C18 C16 121.13(10) . . ?
C20 C19 C18 120.61(12) . . ?
C20 C19 H19A 119.7 . . ?
C18 C19 H19A 119.7 . . ?
C21 C20 C19 120.33(12) . . ?
C21 C20 H20A 119.8 . . ?
C19 C20 H20A 119.8 . . ?
C20 C21 C22 119.76(12) . . ?
C20 C21 H21A 120.1 . . ?
C22 C21 H21A 120.1 . . ?
C21 C22 C23 120.02(12) . . ?
C21 C22 H22A 120.0 . . ?
C23 C22 H22A 120.0 . . ?
C22 C23 C18 120.71(11) . . ?
C22 C23 H23A 119.6 . . ?
C18 C23 H23A 119.6 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 F6 1.5874(10) . ?
P1 F2 1.5923(9) . ?
P1 F5 1.6007(9) . ?
P1 F4 1.6024(9) . ?
P1 F1 1.6072(8) . ?
P1 F3 1.6108(9) . ?
N1 C2 1.3453(14) . ?
N1 C6 1.3528(14) . ?
N1 C7 1.4794(14) . ?
C2 C3 1.3790(16) . ?
C2 H2A 0.9500 . ?
C3 C4 1.4007(16) . ?
C3 H3A 0.9500 . ?
C4 C5 1.4033(15) . ?
C4 C8 1.4809(15) . ?
C5 C6 1.3779(15) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.3833(18) . ?
C8 C17 1.4451(16) . ?
C9 C10 1.4109(19) . ?
C9 H9A 0.9500 . ?
C10 C11 1.363(2) . ?
C10 H10A 0.9500 . ?
C11 C12 1.422(2) . ?
C11 H11A 0.9500 . ?
C12 C13 1.4216(19) . ?
C12 C17 1.4331(15) . ?
C13 C14 1.367(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.4121(19) . ?
C14 H14A 0.9500 . ?
C15 C16 1.3881(16) . ?
C15 H15A 0.9500 . ?
C16 C17 1.4370(17) . ?
C16 C18 1.4872(15) . ?
C18 C23 1.3990(15) . ?
C18 C19 1.4013(16) . ?
C19 C20 1.393(2) . ?
C19 H19A 0.9500 . ?
C20 C21 1.386(2) . ?
C20 H20A 0.9500 . ?
C21 C22 1.393(2) . ?
C21 H21A 0.9500 . ?
C22 C23 1.3955(16) . ?
C22 H22A 0.9500 . ?
C23 H23A 0.9500 . ?
