#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/21/2222181.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2222181
loop_
_publ_author_name
'Wang, Gui-Yu'
'Zhang, Shi-Lu'
'Qin, Da-Bin'
_publ_section_title
;
 3-(9-Anthrylmethyl)-1-benzylperimidinium hexafluorophosphate
;
_journal_coeditor_code           XU2514
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1274
_journal_paper_doi               10.1107/S1600536809017140
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C33 H25 N2 + , F6 P -'
_chemical_formula_moiety         'C33 H25 N2 + , F6 P -'
_chemical_formula_sum            'C33 H25 F6 N2 P'
_chemical_formula_weight         594.52
_chemical_name_systematic
;
1-Benzyl-3-methylanthraceneperimidinium hexafluorophosphate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                94.436(4)
_cell_angle_beta                 95.159(3)
_cell_angle_gamma                110.399(6)
_cell_formula_units_Z            2
_cell_length_a                   9.9596(13)
_cell_length_b                   11.8644(17)
_cell_length_c                   11.8994(12)
_cell_measurement_reflns_used    3227
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.2
_cell_volume                     1303.6(3)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2004)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2004)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2004)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'CrystalStructure (Rigaku/MSC, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0484
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9272
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.20
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.486
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         4823
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0418
_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)+(0.0672P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1125
_reflns_number_gt                3619
_reflns_number_total             4823
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2514.cif
_cod_data_source_block           I
_cod_database_code               2222181
_cod_database_fobs_code          2222181
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.65525(14) 0.26739(12) 0.34502(11) 0.0171(3) Uani d . 1 . .
N N2 0.76633(15) 0.21452(12) 0.19570(11) 0.0166(3) Uani d . 1 . .
C C1 0.7929(2) 0.54158(17) 0.41449(17) 0.0318(5) Uani d . 1 . .
H H1 0.8104 0.5239 0.3391 0.038 Uiso calc R 1 . .
C C2 0.8809(2) 0.64882(17) 0.47870(18) 0.0370(5) Uani d . 1 . .
H H2 0.9593 0.7036 0.4478 0.044 Uiso calc R 1 . .
C C3 0.8547(2) 0.67608(17) 0.58745(17) 0.0313(5) Uani d . 1 . .
H H3 0.9134 0.7505 0.6308 0.038 Uiso calc R 1 . .
C C4 0.7426(2) 0.59450(16) 0.63322(16) 0.0272(4) Uani d . 1 . .
H H4 0.7254 0.6122 0.7087 0.033 Uiso calc R 1 . .
C C5 0.65546(19) 0.48705(16) 0.56896(15) 0.0243(4) Uani d . 1 . .
H H5 0.5785 0.4316 0.6007 0.029 Uiso calc R 1 . .
C C6 0.67932(18) 0.45972(15) 0.45940(15) 0.0209(4) Uani d . 1 . .
C C7 0.57901(18) 0.34585(15) 0.38640(15) 0.0209(4) Uani d . 1 . .
H H7A 0.5035 0.2998 0.4312 0.025 Uiso calc R 1 . .
H H7B 0.5306 0.3689 0.3204 0.025 Uiso calc R 1 . .
C C8 0.68755(18) 0.18549(14) 0.41469(14) 0.0182(4) Uani d . 1 . .
C C9 0.64948(18) 0.17407(15) 0.52252(14) 0.0230(4) Uani d . 1 . .
H H9 0.6024 0.2235 0.5550 0.028 Uiso calc R 1 . .
C C10 0.68127(19) 0.08799(16) 0.58429(16) 0.0264(4) Uani d . 1 . .
H H10 0.6532 0.0783 0.6582 0.032 Uiso calc R 1 . .
C C11 0.75186(19) 0.01810(16) 0.53968(16) 0.0266(4) Uani d . 1 . .
H H11 0.7727 -0.0389 0.5832 0.032 Uiso calc R 1 . .
C C12 0.79414(19) 0.02947(15) 0.43000(15) 0.0223(4) Uani d . 1 . .
C C13 0.86924(19) -0.03935(15) 0.38004(16) 0.0254(4) Uani d . 1 . .
H H13 0.8926 -0.0969 0.4213 0.030 Uiso calc R 1 . .
C C14 0.90839(19) -0.02426(15) 0.27382(16) 0.0250(4) Uani d . 1 . .
H H14 0.9593 -0.0712 0.2427 0.030 Uiso calc R 1 . .
C C15 0.87524(18) 0.05926(14) 0.20896(15) 0.0203(4) Uani d . 1 . .
H H15 0.9025 0.0684 0.1348 0.024 Uiso calc R 1 . .
C C16 0.80270(17) 0.12715(14) 0.25529(14) 0.0171(4) Uani d . 1 . .
C C17 0.69340(17) 0.27509(14) 0.24203(14) 0.0168(4) Uani d . 1 . .
H H17 0.6660 0.3287 0.1978 0.020 Uiso calc R 1 . .
C C18 0.76120(17) 0.11481(14) 0.36533(14) 0.0177(4) Uani d . 1 . .
C C19 0.81402(19) 0.23771(15) 0.08085(14) 0.0204(4) Uani d . 1 . .
H H19A 0.7622 0.1649 0.0260 0.024 Uiso calc R 1 . .
H H19B 0.9186 0.2525 0.0851 0.024 Uiso calc R 1 . .
C C20 0.78569(18) 0.34486(15) 0.03857(14) 0.0189(4) Uani d . 1 . .
C C21 0.67085(18) 0.32839(15) -0.04710(14) 0.0198(4) Uani d . 1 . .
C C22 0.58415(19) 0.21358(15) -0.10874(15) 0.0232(4) Uani d . 1 . .
H H22 0.6033 0.1432 -0.0922 0.028 Uiso calc R 1 . .
C C23 0.4749(2) 0.20365(16) -0.19052(15) 0.0276(4) Uani d . 1 . .
H H23 0.4210 0.1267 -0.2316 0.033 Uiso calc R 1 . .
C C24 0.4395(2) 0.30512(17) -0.21595(16) 0.0295(4) Uani d . 1 . .
H H24 0.3605 0.2955 -0.2716 0.035 Uiso calc R 1 . .
C C25 0.51861(19) 0.41642(17) -0.16064(15) 0.0265(4) Uani d . 1 . .
H H25 0.4944 0.4843 -0.1780 0.032 Uiso calc R 1 . .
C C26 0.63810(19) 0.43274(15) -0.07648(14) 0.0205(4) Uani d . 1 . .
C C27 0.72088(18) 0.54694(15) -0.02117(14) 0.0221(4) Uani d . 1 . .
H H27 0.6969 0.6148 -0.0393 0.026 Uiso calc R 1 . .
C C28 0.83807(18) 0.56432(15) 0.06025(14) 0.0204(4) Uani d . 1 . .
C C29 0.92430(19) 0.68278(15) 0.11489(15) 0.0244(4) Uani d . 1 . .
H H29 0.9021 0.7508 0.0948 0.029 Uiso calc R 1 . .
C C30 1.0374(2) 0.69881(16) 0.19508(16) 0.0264(4) Uani d . 1 . .
H H30 1.0940 0.7779 0.2304 0.032 Uiso calc R 1 . .
C C31 1.07145(19) 0.59810(16) 0.22627(15) 0.0249(4) Uani d . 1 . .
H H31 1.1508 0.6104 0.2825 0.030 Uiso calc R 1 . .
C C32 0.99184(18) 0.48391(15) 0.17669(14) 0.0208(4) Uani d . 1 . .
H H32 1.0161 0.4177 0.1994 0.025 Uiso calc R 1 . .
C C33 0.87223(18) 0.46190(15) 0.09092(14) 0.0192(4) Uani d . 1 . .
F F1 0.40915(11) 0.24779(9) 0.12667(9) 0.0327(3) Uani d . 1 A .
F F2 0.2510(4) 0.1531(2) 0.2443(3) 0.0547(10) Uani d P 0.645(4) A 1
F F3 0.1733(2) 0.1364(2) 0.0581(3) 0.0549(11) Uani d P 0.645(4) A 1
F F4 0.3399(3) 0.05825(18) 0.01761(18) 0.0455(8) Uani d P 0.645(4) A 1
F F5 0.4188(2) 0.07577(17) 0.2026(2) 0.0432(8) Uani d P 0.645(4) A 1
F F2' 0.3311(7) 0.1323(6) 0.2590(4) 0.075(3) Uani d P 0.355(4) A 2
F F3' 0.1746(4) 0.1825(3) 0.1473(5) 0.0555(17) Uani d P 0.355(4) A 2
F F4' 0.2570(6) 0.1275(4) -0.0041(3) 0.066(2) Uani d P 0.355(4) A 2
F F5' 0.4147(6) 0.0736(4) 0.1032(8) 0.087(3) Uani d P 0.355(4) A 2
F F6 0.18320(13) -0.02144(10) 0.13375(11) 0.0468(3) Uani d . 1 A .
P P1 0.29507(5) 0.11278(4) 0.12934(4) 0.02730(16) Uani d . 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C17 N1 C8 . . 120.62(14) ?
C17 N1 C7 . . 118.36(14) ?
C8 N1 C7 . . 121.02(14) ?
C17 N2 C16 . . 120.01(14) ?
C17 N2 C19 . . 120.46(14) ?
C16 N2 C19 . . 119.52(13) ?
C2 C1 C6 . . 120.56(18) ?
C2 C1 H1 . . 119.7 ?
C6 C1 H1 . . 119.7 ?
C3 C2 C1 . . 120.07(18) ?
C3 C2 H2 . . 120.0 ?
C1 C2 H2 . . 120.0 ?
C2 C3 C4 . . 119.72(17) ?
C2 C3 H3 . . 120.1 ?
C4 C3 H3 . . 120.1 ?
C3 C4 C5 . . 119.99(18) ?
C3 C4 H4 . . 120.0 ?
C5 C4 H4 . . 120.0 ?
C6 C5 C4 . . 120.76(17) ?
C6 C5 H5 . . 119.6 ?
C4 C5 H5 . . 119.6 ?
C5 C6 C1 . . 118.88(16) ?
C5 C6 C7 . . 120.93(16) ?
C1 C6 C7 . . 120.11(16) ?
N1 C7 C6 . . 112.65(13) ?
N1 C7 H7A . . 109.1 ?
C6 C7 H7A . . 109.1 ?
N1 C7 H7B . . 109.1 ?
C6 C7 H7B . . 109.1 ?
H7A C7 H7B . . 107.8 ?
C9 C8 C18 . . 121.59(16) ?
C9 C8 N1 . . 122.67(15) ?
C18 C8 N1 . . 115.74(15) ?
C8 C9 C10 . . 119.04(17) ?
C8 C9 H9 . . 120.5 ?
C10 C9 H9 . . 120.5 ?
C11 C10 C9 . . 121.11(17) ?
C11 C10 H10 . . 119.4 ?
C9 C10 H10 . . 119.4 ?
C10 C11 C12 . . 120.93(17) ?
C10 C11 H11 . . 119.5 ?
C12 C11 H11 . . 119.5 ?
C11 C12 C13 . . 123.40(16) ?
C11 C12 C18 . . 118.90(16) ?
C13 C12 C18 . . 117.71(16) ?
C14 C13 C12 . . 121.02(16) ?
C14 C13 H13 . . 119.5 ?
C12 C13 H13 . . 119.5 ?
C13 C14 C15 . . 121.62(17) ?
C13 C14 H14 . . 119.2 ?
C15 C14 H14 . . 119.2 ?
C16 C15 C14 . . 118.59(17) ?
C16 C15 H15 . . 120.7 ?
C14 C15 H15 . . 120.7 ?
C15 C16 C18 . . 121.50(16) ?
C15 C16 N2 . . 122.08(16) ?
C18 C16 N2 . . 116.42(15) ?
N2 C17 N1 . . 125.09(15) ?
N2 C17 H17 . . 117.5 ?
N1 C17 H17 . . 117.5 ?
C16 C18 C8 . . 122.03(15) ?
C16 C18 C12 . . 119.56(16) ?
C8 C18 C12 . . 118.41(16) ?
N2 C19 C20 . . 112.12(13) ?
N2 C19 H19A . . 109.2 ?
C20 C19 H19A . . 109.2 ?
N2 C19 H19B . . 109.2 ?
C20 C19 H19B . . 109.2 ?
H19A C19 H19B . . 107.9 ?
C21 C20 C33 . . 120.73(15) ?
C21 C20 C19 . . 120.84(15) ?
C33 C20 C19 . . 118.35(15) ?
C20 C21 C22 . . 123.91(16) ?
C20 C21 C26 . . 118.90(15) ?
C22 C21 C26 . . 117.19(16) ?
C23 C22 C21 . . 121.10(17) ?
C23 C22 H22 . . 119.5 ?
C21 C22 H22 . . 119.5 ?
C22 C23 C24 . . 121.57(17) ?
C22 C23 H23 . . 119.2 ?
C24 C23 H23 . . 119.2 ?
C25 C24 C23 . . 119.87(18) ?
C25 C24 H24 . . 120.1 ?
C23 C24 H24 . . 120.1 ?
C24 C25 C26 . . 120.87(17) ?
C24 C25 H25 . . 119.6 ?
C26 C25 H25 . . 119.6 ?
C27 C26 C25 . . 120.98(16) ?
C27 C26 C21 . . 119.68(16) ?
C25 C26 C21 . . 119.32(16) ?
C26 C27 C28 . . 121.61(16) ?
C26 C27 H27 . . 119.2 ?
C28 C27 H27 . . 119.2 ?
C27 C28 C29 . . 121.05(16) ?
C27 C28 C33 . . 119.59(15) ?
C29 C28 C33 . . 119.36(16) ?
C30 C29 C28 . . 120.69(16) ?
C30 C29 H29 . . 119.7 ?
C28 C29 H29 . . 119.7 ?
C29 C30 C31 . . 120.31(16) ?
C29 C30 H30 . . 119.8 ?
C31 C30 H30 . . 119.8 ?
C32 C31 C30 . . 120.85(17) ?
C32 C31 H31 . . 119.6 ?
C30 C31 H31 . . 119.6 ?
C31 C32 C33 . . 121.20(16) ?
C31 C32 H32 . . 119.4 ?
C33 C32 H32 . . 119.4 ?
C20 C33 C32 . . 123.01(16) ?
C20 C33 C28 . . 119.38(16) ?
C32 C33 C28 . . 117.59(15) ?
F5' P1 F2' . . 97.4(5) ?
F5' P1 F3 . . 134.8(4) ?
F2' P1 F3 . . 127.7(3) ?
F5' P1 F2 . . 132.0(4) ?
F2' P1 F2 . . 34.6(3) ?
F3 P1 F2 . . 93.12(18) ?
F5' P1 F4 . . 44.5(3) ?
F2' P1 F4 . . 141.3(4) ?
F3 P1 F4 . . 90.88(17) ?
F2 P1 F4 . . 173.66(14) ?
F5' P1 F6 . . 94.76(17) ?
F2' P1 F6 . . 91.31(19) ?
F3 P1 F6 . . 87.39(9) ?
F2 P1 F6 . . 88.91(11) ?
F4 P1 F6 . . 86.36(8) ?
F5' P1 F1 . . 84.92(17) ?
F2' P1 F1 . . 87.91(19) ?
F3 P1 F1 . . 93.42(9) ?
F2 P1 F1 . . 90.69(11) ?
F4 P1 F1 . . 93.98(8) ?
F6 P1 F1 . . 179.11(7) ?
F5' P1 F4' . . 91.6(4) ?
F2' P1 F4' . . 165.3(3) ?
F3 P1 F4' . . 43.9(2) ?
F2 P1 F4' . . 135.0(3) ?
F4 P1 F4' . . 50.3(2) ?
F6 P1 F4' . . 99.54(15) ?
F1 P1 F4' . . 81.30(15) ?
F5' P1 F5 . . 43.9(3) ?
F2' P1 F5 . . 54.1(3) ?
F3 P1 F5 . . 175.39(11) ?
F2 P1 F5 . . 88.54(16) ?
F4 P1 F5 . . 87.11(15) ?
F6 P1 F5 . . 88.35(9) ?
F1 P1 F5 . . 90.85(8) ?
F4' P1 F5 . . 135.5(3) ?
F5' P1 F3' . . 168.7(2) ?
F2' P1 F3' . . 86.9(3) ?
F3 P1 F3' . . 41.43(18) ?
F2 P1 F3' . . 52.9(2) ?
F4 P1 F3' . . 131.8(2) ?
F6 P1 F3' . . 95.57(13) ?
F1 P1 F3' . . 84.82(13) ?
F4' P1 F3' . . 82.2(3) ?
F5 P1 F3' . . 141.0(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C17 . 1.316(2) ?
N1 C8 . 1.425(2) ?
N1 C7 . 1.475(2) ?
N2 C17 . 1.312(2) ?
N2 C16 . 1.428(2) ?
N2 C19 . 1.501(2) ?
C1 C2 . 1.387(3) ?
C1 C6 . 1.390(3) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.379(3) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.385(3) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.386(2) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.380(2) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.516(2) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 C9 . 1.374(2) ?
C8 C18 . 1.420(2) ?
C9 C10 . 1.408(2) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.367(3) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.409(3) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.418(3) ?
C12 C18 . 1.425(2) ?
C13 C14 . 1.363(3) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.410(2) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.372(2) ?
C15 H15 . 0.9500 ?
C16 C18 . 1.411(2) ?
C17 H17 . 0.9500 ?
C19 C20 . 1.507(2) ?
C19 H19A . 0.9900 ?
C19 H19B . 0.9900 ?
C20 C21 . 1.410(2) ?
C20 C33 . 1.412(2) ?
C21 C22 . 1.432(2) ?
C21 C26 . 1.445(2) ?
C22 C23 . 1.359(2) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.414(3) ?
C23 H23 . 0.9500 ?
C24 C25 . 1.358(2) ?
C24 H24 . 0.9500 ?
C25 C26 . 1.432(2) ?
C25 H25 . 0.9500 ?
C26 C27 . 1.391(2) ?
C27 C28 . 1.393(2) ?
C27 H27 . 0.9500 ?
C28 C29 . 1.433(2) ?
C28 C33 . 1.435(2) ?
C29 C30 . 1.359(3) ?
C29 H29 . 0.9500 ?
C30 C31 . 1.417(2) ?
C30 H30 . 0.9500 ?
C31 C32 . 1.362(2) ?
C31 H31 . 0.9500 ?
C32 C33 . 1.433(2) ?
C32 H32 . 0.9500 ?
F1 P1 . 1.6135(11) ?
F2 P1 . 1.564(2) ?
F3 P1 . 1.5353(19) ?
F4 P1 . 1.600(2) ?
F5 P1 . 1.6477(19) ?
F2' P1 . 1.533(5) ?
F3' P1 . 1.697(4) ?
F4' P1 . 1.636(4) ?
F5' P1 . 1.471(4) ?
F6 P1 . 1.6021(12) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C10 H10 F5 2_656 0.95 2.52 3.327(3) 142
C11 H11 F2 2_656 0.95 2.53 3.393(4) 151
C19 H19A F4 2_655 0.99 2.48 3.368(3) 150
C27 H27 F1 2_665 0.95 2.47 3.401(2) 165
C29 H29 F3 2_665 0.95 2.55 3.400(3) 149
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -1.1(3) ?
C1 C2 C3 C4 . . . . 1.7(3) ?
C2 C3 C4 C5 . . . . -1.3(3) ?
C3 C4 C5 C6 . . . . 0.3(3) ?
C4 C5 C6 C1 . . . . 0.3(3) ?
C4 C5 C6 C7 . . . . -176.36(16) ?
C2 C1 C6 C5 . . . . 0.1(3) ?
C2 C1 C6 C7 . . . . 176.79(17) ?
C17 N1 C7 C6 . . . . -97.27(17) ?
C8 N1 C7 C6 . . . . 82.48(19) ?
C5 C6 C7 N1 . . . . -123.00(17) ?
C1 C6 C7 N1 . . . . 60.4(2) ?
C17 N1 C8 C9 . . . . -179.79(15) ?
C7 N1 C8 C9 . . . . 0.5(2) ?
C17 N1 C8 C18 . . . . -0.3(2) ?
C7 N1 C8 C18 . . . . 179.97(13) ?
C18 C8 C9 C10 . . . . -1.6(3) ?
N1 C8 C9 C10 . . . . 177.89(15) ?
C8 C9 C10 C11 . . . . 1.5(3) ?
C9 C10 C11 C12 . . . . -0.5(3) ?
C10 C11 C12 C13 . . . . 179.12(16) ?
C10 C11 C12 C18 . . . . -0.4(3) ?
C11 C12 C13 C14 . . . . -179.60(16) ?
C18 C12 C13 C14 . . . . 0.0(2) ?
C12 C13 C14 C15 . . . . -0.5(3) ?
C13 C14 C15 C16 . . . . 0.5(3) ?
C14 C15 C16 C18 . . . . 0.0(2) ?
C14 C15 C16 N2 . . . . 179.37(15) ?
C17 N2 C16 C15 . . . . 178.13(14) ?
C19 N2 C16 C15 . . . . -2.8(2) ?
C17 N2 C16 C18 . . . . -2.4(2) ?
C19 N2 C16 C18 . . . . 176.65(13) ?
C16 N2 C17 N1 . . . . 3.9(2) ?
C19 N2 C17 N1 . . . . -175.18(14) ?
C8 N1 C17 N2 . . . . -2.5(2) ?
C7 N1 C17 N2 . . . . 177.28(14) ?
C15 C16 C18 C8 . . . . 179.28(15) ?
N2 C16 C18 C8 . . . . -0.2(2) ?
C15 C16 C18 C12 . . . . -0.4(2) ?
N2 C16 C18 C12 . . . . -179.89(14) ?
C9 C8 C18 C16 . . . . -179.03(15) ?
N1 C8 C18 C16 . . . . 1.5(2) ?
C9 C8 C18 C12 . . . . 0.7(2) ?
N1 C8 C18 C12 . . . . -178.82(14) ?
C11 C12 C18 C16 . . . . -179.93(15) ?
C13 C12 C18 C16 . . . . 0.5(2) ?
C11 C12 C18 C8 . . . . 0.3(2) ?
C13 C12 C18 C8 . . . . -179.26(14) ?
C17 N2 C19 C20 . . . . 7.6(2) ?
C16 N2 C19 C20 . . . . -171.50(14) ?
N2 C19 C20 C21 . . . . -104.92(18) ?
N2 C19 C20 C33 . . . . 71.8(2) ?
C33 C20 C21 C22 . . . . 176.07(16) ?
C19 C20 C21 C22 . . . . -7.2(3) ?
C33 C20 C21 C26 . . . . -3.2(2) ?
C19 C20 C21 C26 . . . . 173.47(15) ?
C20 C21 C22 C23 . . . . -179.96(17) ?
C26 C21 C22 C23 . . . . -0.7(3) ?
C21 C22 C23 C24 . . . . -1.8(3) ?
C22 C23 C24 C25 . . . . 2.2(3) ?
C23 C24 C25 C26 . . . . 0.0(3) ?
C24 C25 C26 C27 . . . . 178.84(17) ?
C24 C25 C26 C21 . . . . -2.5(3) ?
C20 C21 C26 C27 . . . . 0.8(2) ?
C22 C21 C26 C27 . . . . -178.56(15) ?
C20 C21 C26 C25 . . . . -177.89(15) ?
C22 C21 C26 C25 . . . . 2.8(2) ?
C25 C26 C27 C28 . . . . -179.52(16) ?
C21 C26 C27 C28 . . . . 1.8(3) ?
C26 C27 C28 C29 . . . . 178.68(16) ?
C26 C27 C28 C33 . . . . -2.0(3) ?
C27 C28 C29 C30 . . . . 179.29(17) ?
C33 C28 C29 C30 . . . . 0.0(3) ?
C28 C29 C30 C31 . . . . -0.3(3) ?
C29 C30 C31 C32 . . . . 0.0(3) ?
C30 C31 C32 C33 . . . . 0.6(3) ?
C21 C20 C33 C32 . . . . -178.74(16) ?
C19 C20 C33 C32 . . . . 4.5(3) ?
C21 C20 C33 C28 . . . . 3.1(3) ?
C19 C20 C33 C28 . . . . -173.69(15) ?
C31 C32 C33 C20 . . . . -179.07(17) ?
C31 C32 C33 C28 . . . . -0.8(3) ?
C27 C28 C33 C20 . . . . -0.5(3) ?
C29 C28 C33 C20 . . . . 178.87(15) ?
C27 C28 C33 C32 . . . . -178.75(15) ?
C29 C28 C33 C32 . . . . 0.6(2) ?
