##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     'SHELXL97'
_journal_date_recd_electronic     2007-07-19
_journal_date_accepted     2007-08-06
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      9
_journal_page_first     o3785
_journal_page_last     o3785
_journal_paper_category     QO
_journal_coeditor_code     CI2422
_publ_contact_author_name     'Xiao-Na Fan'
_publ_contact_author_address
;
Department of Pharmacy
GanNan Medical University
GanZhou 341000
People's Republic of China
;
_publ_contact_author_email     fxn9918@126.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
1-Benzyl-3-(8-methoxyquinolin-2-ylmethyl)imidazolium hexafluoridophosphate
;
loop_
    _publ_author_name
    _publ_author_address
    'Xiao-Na Fan'
;
Department of Pharmacy
Gannan Medical University
Ganzhou 341000
People's Republic of China
;
    'Guo-Lun XiaHou'
;
Department of Pharmacy
Gannan Medical University
Ganzhou 341000
People's Republic of China
;
    'Zhi-Qin Huang'
;
Department of Pharmacy
Gannan Medical University
Ganzhou 341000
People's Republic of China
;
    'Ye-Chun Ding'
;
Department of Pharmacy
Gannan Medical University
Ganzhou 341000
People's Republic of China
;
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
1-Benzyl-3-(8-methoxyquinolin-2-ylmethyl)imidazolium hexafluoridophosphate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C21 H20 N3 O + , F6 P -'
_chemical_formula_sum     'C21 H20 F6 N3 O P'
_chemical_formula_iupac     'C21 H20 N3 O + , F6 P -'
_chemical_formula_weight     475.37
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     12.272(3)
_cell_length_b     12.537(3)
_cell_length_c     14.361(3)
_cell_angle_alpha     90.847(3)
_cell_angle_beta     91.539(3)
_cell_angle_gamma     93.809(3)
_cell_volume     2203.5(8)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2858
_cell_measurement_theta_min     2.65
_cell_measurement_theta_max     23.56
_cell_measurement_temperature     291(2)
_exptl_crystal_description     block
_exptl_crystal_colour     white
_exptl_crystal_size_max     0.49
_exptl_crystal_size_mid     0.45
_exptl_crystal_size_min     0.43
_exptl_crystal_density_diffrn     1.433
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     976
_exptl_absorpt_coefficient_mu     0.193
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1997)'
_exptl_absorpt_correction_T_min     0.9113
_exptl_absorpt_correction_T_max     0.9215
_exptl_special_details
;
;
_diffrn_ambient_temperature     291(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     15491
_diffrn_reflns_av_R_equivalents     0.0378
_diffrn_reflns_av_sigmaI/netI     0.0622
_diffrn_reflns_theta_min     2.40
_diffrn_reflns_theta_max     25.50
_diffrn_reflns_theta_full     25.50
_diffrn_measured_fraction_theta_max     0.970
_diffrn_measured_fraction_theta_full     0.970
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     17
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     7961
_reflns_number_gt     4602
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1175
_refine_ls_R_factor_gt     0.0653
_refine_ls_wR_factor_gt     0.1864
_refine_ls_wR_factor_ref     0.2153
_refine_ls_goodness_of_fit_ref     1.045
_refine_ls_restrained_S_all     1.092
_refine_ls_number_reflns     7961
_refine_ls_number_parameters     708
_refine_ls_number_restraints     240
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0928P)²+1.4093P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.500
_refine_diff_density_min     -0.243
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_extinction_coef     0.0057(11)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
    'O' 'O' 0.0106 0.0060
                         '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'
    'P' 'P' 0.1023 0.0942
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 1997)'
_computing_cell_refinement     'SAINT (Bruker, 1997)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 1997)'
_computing_publication_material     'SHELXL97'
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
    P P1 0.6866(3) 0.2339(3) 0.4728(3) 0.0605(19) Uani d PDU 0.742(10) A 1
    F F1 0.6701(4) 0.2242(6) 0.3625(3) 0.109(2) Uani d PDU 0.742(10) A 1
    F F2 0.7707(5) 0.1462(5) 0.4689(5) 0.124(2) Uani d PDU 0.742(10) A 1
    F F3 0.5890(6) 0.1459(6) 0.4837(5) 0.111(2) Uani d PDU 0.742(10) A 1
    F F4 0.7030(4) 0.2430(5) 0.5810(3) 0.104(2) Uani d PDU 0.742(10) A 1
    F F5 0.6003(5) 0.3196(5) 0.4755(5) 0.135(3) Uani d PDU 0.742(10) A 1
    F F6 0.7822(5) 0.3205(5) 0.4588(4) 0.109(2) Uani d PDU 0.742(10) A 1
    P P1' 0.6893(9) 0.2309(9) 0.4643(8) 0.063(6) Uani d PDU 0.258(10) A 2
    F F1' 0.7114(11) 0.1534(11) 0.3811(10) 0.090(5) Uani d PDU 0.258(10) A 2
    F F2' 0.7923(13) 0.1921(16) 0.5154(13) 0.158(9) Uani d PDU 0.258(10) A 2
    F F3' 0.6187(16) 0.1361(14) 0.5069(14) 0.124(9) Uani d PDU 0.258(10) A 2
    F F4' 0.6676(14) 0.3058(15) 0.5485(13) 0.140(7) Uani d PDU 0.258(10) A 2
    F F5' 0.5902(10) 0.2719(14) 0.4092(13) 0.128(7) Uani d PDU 0.258(10) A 2
    F F6' 0.7659(12) 0.3220(10) 0.4227(13) 0.094(6) Uani d PDU 0.258(10) A 2
    P P2 0.1795(4) 0.7468(4) 0.0546(3) 0.0571(12) Uani d PDU 0.739(19) B 1
    F F7 0.2725(6) 0.6773(5) 0.0189(7) 0.110(3) Uani d PDU 0.739(19) B 1
    F F8 0.1989(5) 0.7013(7) 0.1553(4) 0.090(2) Uani d PDU 0.739(19) B 1
    F F9 0.0912(8) 0.6513(7) 0.0333(7) 0.114(3) Uani d PDU 0.739(19) B 1
    F F10 0.0869(6) 0.8149(7) 0.0922(7) 0.130(3) Uani d PDU 0.739(19) B 1
    F F11 0.1606(9) 0.7891(6) -0.0466(4) 0.116(3) Uani d PDU 0.739(19) B 1
    F F12 0.2675(6) 0.8413(6) 0.0764(6) 0.092(2) Uani d PDU 0.739(19) B 1
    P P2' 0.1689(11) 0.7337(12) 0.0456(10) 0.067(5) Uani d PDU 0.261(19) B 2
    F F7' 0.2338(19) 0.6744(15) -0.0290(19) 0.129(8) Uani d PDU 0.261(19) B 2
    F F8' 0.2211(17) 0.6680(15) 0.1248(17) 0.101(7) Uani d PDU 0.261(19) B 2
    F F9' 0.0738(13) 0.6427(13) 0.0332(13) 0.062(5) Uani d PDU 0.261(19) B 2
    F F10' 0.1024(19) 0.7933(17) 0.1193(12) 0.113(7) Uani d PDU 0.261(19) B 2
    F F11' 0.1105(19) 0.7986(15) -0.0311(12) 0.104(7) Uani d PDU 0.261(19) B 2
    F F12' 0.2669(16) 0.8208(16) 0.0533(18) 0.109(9) Uani d PDU 0.261(19) B 2
    O O1 0.7717(3) 0.6213(3) 0.5771(3) 0.0933(11) Uani d . 1 . .
    O O2 0.7504(2) -0.1017(2) 1.0211(2) 0.0746(9) Uani d . 1 . .
    N N1 0.9222(3) 0.6509(3) 0.4472(2) 0.0546(8) Uani d . 1 . .
    N N2 1.0364(3) 0.4949(3) 0.3131(2) 0.0541(8) Uani d . 1 . .
    N N3 0.9645(3) 0.3409(3) 0.2674(2) 0.0564(9) Uani d . 1 . .
    N N4 0.5105(3) 0.1467(3) 0.7904(3) 0.0608(9) Uani d . 1 . .
    N N5 0.4442(2) -0.0133(3) 0.8162(2) 0.0520(8) Uani d . 1 . .
    N N6 0.5660(3) -0.1618(2) 0.9259(2) 0.0508(8) Uani d . 1 . .
    C C1 0.7622(4) 0.7075(4) 0.5216(4) 0.0701(12) Uani d . 1 . .
    C C2 0.6811(4) 0.7791(5) 0.5282(4) 0.0916(17) Uani d . 1 . .
    H H2 0.6277 0.7697 0.5726 0.110 Uiso calc R 1 . .
    C C3 0.6800(5) 0.8665(5) 0.4669(5) 0.103(2) Uani d . 1 . .
    H H3 0.6248 0.9136 0.4713 0.124 Uiso calc R 1 . .
    C C4 0.7548(5) 0.8831(4) 0.4037(5) 0.0972(18) Uani d . 1 . .
    H H4 0.7527 0.9422 0.3655 0.117 Uiso calc R 1 . .
    C C5 0.8392(4) 0.8110(4) 0.3936(3) 0.0713(13) Uani d . 1 . .
    C C6 0.9207(5) 0.8250(4) 0.3281(3) 0.0872(16) Uani d . 1 . .
    H H6 0.9211 0.8825 0.2879 0.105 Uiso calc R 1 . .
    C C7 1.0005(5) 0.7529(4) 0.3233(3) 0.0805(14) Uani d . 1 . .
    H H7 1.0561 0.7618 0.2808 0.097 Uiso calc R 1 . .
    C C8 0.9964(3) 0.6664(3) 0.3835(3) 0.0577(10) Uani d . 1 . .
    C C9 0.8432(3) 0.7221(3) 0.4532(3) 0.0580(10) Uani d . 1 . .
    C C10 0.6958(6) 0.6066(7) 0.6503(6) 0.170(4) Uani d . 1 . .
    H H10A 0.7016 0.6682 0.6910 0.255 Uiso calc R 1 . .
    H H10B 0.7120 0.5444 0.6850 0.255 Uiso calc R 1 . .
    H H10C 0.6230 0.5972 0.6241 0.255 Uiso calc R 1 . .
    C C11 1.0793(4) 0.5831(3) 0.3756(3) 0.0650(12) Uani d . 1 . .
    H H11A 1.1465 0.6154 0.3513 0.078 Uiso calc R 1 . .
    H H11B 1.0956 0.5554 0.4368 0.078 Uiso calc R 1 . .
    C C12 1.0219(4) 0.4975(4) 0.2186(3) 0.0746(14) Uani d . 1 . .
    H H12 1.0397 0.5553 0.1808 0.090 Uiso calc R 1 . .
    C C13 0.9773(4) 0.4018(4) 0.1901(3) 0.0714(13) Uani d . 1 . .
    H H13 0.9586 0.3808 0.1291 0.086 Uiso calc R 1 . .
    C C14 1.0005(3) 0.3990(3) 0.3407(3) 0.0561(10) Uani d . 1 . .
    H H14 1.0007 0.3761 0.4020 0.067 Uiso calc R 1 . .
    C C15 0.9222(4) 0.2273(4) 0.2682(3) 0.0706(12) Uani d . 1 . .
    H H15A 0.8832 0.2097 0.2098 0.085 Uiso calc R 1 . .
    H H15B 0.8708 0.2177 0.3181 0.085 Uiso calc R 1 . .
    C C16 1.0119(4) 0.1517(3) 0.2818(3) 0.0630(11) Uani d . 1 . .
    C C17 1.0769(5) 0.1275(4) 0.2090(4) 0.0953(18) Uani d . 1 . .
    H H17 1.0663 0.1589 0.1515 0.114 Uiso calc R 1 . .
    C C18 1.1584(6) 0.0565(5) 0.2203(6) 0.118(2) Uani d . 1 . .
    H H18 1.2016 0.0392 0.1708 0.142 Uiso calc R 1 . .
    C C19 1.1735(5) 0.0125(5) 0.3066(7) 0.114(2) Uani d . 1 . .
    H H19 1.2296 -0.0328 0.3166 0.137 Uiso calc R 1 . .
    C C20 1.1069(6) 0.0351(5) 0.3772(5) 0.1038(19) Uani d . 1 . .
    H H20 1.1157 0.0023 0.4343 0.125 Uiso calc R 1 . .
    C C21 1.0275(5) 0.1047(4) 0.3660(3) 0.0823(15) Uani d . 1 . .
    H H21 0.9838 0.1205 0.4156 0.099 Uiso calc R 1 . .
    C C22 0.7408(3) -0.2053(3) 0.9897(3) 0.0575(11) Uani d . 1 . .
    C C23 0.8181(4) -0.2779(4) 1.0050(3) 0.0728(13) Uani d . 1 . .
    H H23 0.8827 -0.2575 1.0378 0.087 Uiso calc R 1 . .
    C C24 0.7988(5) -0.3843(4) 0.9703(4) 0.0889(18) Uani d . 1 . .
    H H24 0.8512 -0.4333 0.9809 0.107 Uiso calc R 1 . .
    C C25 0.7063(5) -0.4156(4) 0.9225(4) 0.0896(17) Uani d . 1 . .
    H H25 0.6950 -0.4860 0.9010 0.108 Uiso calc R 1 . .
    C C26 0.6255(4) -0.3418(3) 0.9046(3) 0.0672(12) Uani d . 1 . .
    C C27 0.5275(5) -0.3680(4) 0.8540(4) 0.0865(16) Uani d . 1 . .
    H H27 0.5131 -0.4372 0.8304 0.104 Uiso calc R 1 . .
    C C28 0.4540(4) -0.2938(4) 0.8392(4) 0.0763(13) Uani d . 1 . .
    H H28 0.3903 -0.3106 0.8040 0.092 Uiso calc R 1 . .
    C C29 0.4759(4) -0.1903(3) 0.8782(3) 0.0554(10) Uani d . 1 . .
    C C30 0.6423(3) -0.2354(3) 0.9388(3) 0.0525(10) Uani d . 1 . .
    C C31 0.8499(5) -0.0659(5) 1.0692(5) 0.109(2) Uani d . 1 . .
    H H31A 0.8569 -0.1047 1.1259 0.164 Uiso calc R 1 . .
    H H31B 0.8490 0.0091 1.0834 0.164 Uiso calc R 1 . .
    H H31C 0.9106 -0.0780 1.0305 0.164 Uiso calc R 1 . .
    C C32 0.3959(3) -0.1062(3) 0.8645(3) 0.0663(12) Uani d . 1 . .
    H H32A 0.3329 -0.1364 0.8286 0.080 Uiso calc R 1 . .
    H H32B 0.3710 -0.0834 0.9247 0.080 Uiso calc R 1 . .
    C C33 0.4784(4) -0.0108(4) 0.7262(3) 0.0686(13) Uani d . 1 . .
    H H33 0.4739 -0.0678 0.6838 0.082 Uiso calc R 1 . .
    C C34 0.5190(4) 0.0879(4) 0.7103(3) 0.0719(13) Uani d . 1 . .
    H H34 0.5480 0.1125 0.6548 0.086 Uiso calc R 1 . .
    C C35 0.4652(3) 0.0829(3) 0.8536(3) 0.0566(10) Uani d . 1 . .
    H H35 0.4507 0.1028 0.9144 0.068 Uiso calc R 1 . .
    C C36 0.5422(4) 0.2627(4) 0.8036(4) 0.0841(15) Uani d . 1 . .
    H H36A 0.6111 0.2791 0.7736 0.101 Uiso calc R 1 . .
    H H36B 0.5534 0.2784 0.8696 0.101 Uiso calc R 1 . .
    C C37 0.4588(4) 0.3331(3) 0.7649(3) 0.0614(11) Uani d . 1 . .
    C C38 0.4690(5) 0.3775(4) 0.6792(4) 0.0932(18) Uani d . 1 . .
    H H38 0.5280 0.3625 0.6431 0.112 Uiso calc R 1 . .
    C C39 0.3919(7) 0.4451(5) 0.6449(4) 0.110(2) Uani d . 1 . .
    H H39 0.3993 0.4748 0.5863 0.132 Uiso calc R 1 . .
    C C40 0.3081(6) 0.4664(5) 0.6967(6) 0.103(2) Uani d . 1 . .
    H H40 0.2564 0.5108 0.6734 0.123 Uiso calc R 1 . .
    C C41 0.2958(5) 0.4252(5) 0.7827(6) 0.119(2) Uani d . 1 . .
    H H41 0.2375 0.4421 0.8190 0.143 Uiso calc R 1 . .
    C C42 0.3715(4) 0.3580(5) 0.8149(4) 0.0934(17) Uani d . 1 . .
    H H42 0.3626 0.3282 0.8734 0.112 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    P1 F2 . 1.559(5) ?
    P1 F5 . 1.559(5) ?
    P1 F4 . 1.563(5) ?
    P1 F6 . 1.564(5) ?
    P1 F3 . 1.586(5) ?
    P1 F1 . 1.592(5) ?
    P1' F2' . 1.554(9) ?
    P1' F5' . 1.554(9) ?
    P1' F4' . 1.559(9) ?
    P1' F6' . 1.566(9) ?
    P1' F3' . 1.566(10) ?
    P1' F1' . 1.569(9) ?
    P2 F10 . 1.569(5) ?
    P2 F12 . 1.571(6) ?
    P2 F11 . 1.572(5) ?
    P2 F7 . 1.573(5) ?
    P2 F8 . 1.580(5) ?
    P2 F9 . 1.581(6) ?
    P2' F7' . 1.561(9) ?
    P2' F8' . 1.563(9) ?
    P2' F10' . 1.565(9) ?
    P2' F11' . 1.565(9) ?
    P2' F12' . 1.570(10) ?
    P2' F9' . 1.581(10) ?
    O1 C1 . 1.361(6) ?
    O1 C10 . 1.429(6) ?
    O2 C22 . 1.365(5) ?
    O2 C31 . 1.428(6) ?
    N1 C8 . 1.316(5) ?
    N1 C9 . 1.364(5) ?
    N2 C14 . 1.323(5) ?
    N2 C12 . 1.365(5) ?
    N2 C11 . 1.474(5) ?
    N3 C14 . 1.321(5) ?
    N3 C13 . 1.362(5) ?
    N3 C15 . 1.483(5) ?
    N4 C35 . 1.326(5) ?
    N4 C34 . 1.368(6) ?
    N4 C36 . 1.489(6) ?
    N5 C35 . 1.319(5) ?
    N5 C33 . 1.370(5) ?
    N5 C32 . 1.464(5) ?
    N6 C29 . 1.312(5) ?
    N6 C30 . 1.370(5) ?
    C1 C2 . 1.388(6) ?
    C1 C9 . 1.421(6) ?
    C2 C3 . 1.417(8) ?
    C2 H2 . 0.93 ?
    C3 C4 . 1.316(8) ?
    C3 H3 . 0.93 ?
    C4 C5 . 1.427(7) ?
    C4 H4 . 0.93 ?
    C5 C6 . 1.396(7) ?
    C5 C9 . 1.419(6) ?
    C6 C7 . 1.379(7) ?
    C6 H6 . 0.93 ?
    C7 C8 . 1.396(6) ?
    C7 H7 . 0.93 ?
    C8 C11 . 1.510(5) ?
    C10 H10A . 0.96 ?
    C10 H10B . 0.96 ?
    C10 H10C . 0.96 ?
    C11 H11A . 0.97 ?
    C11 H11B . 0.97 ?
    C12 C13 . 1.339(6) ?
    C12 H12 . 0.93 ?
    C13 H13 . 0.93 ?
    C14 H14 . 0.93 ?
    C15 C16 . 1.510(6) ?
    C15 H15A . 0.97 ?
    C15 H15B . 0.97 ?
    C16 C21 . 1.367(6) ?
    C16 C17 . 1.375(6) ?
    C17 C18 . 1.389(8) ?
    C17 H17 . 0.93 ?
    C18 C19 . 1.378(10) ?
    C18 H18 . 0.93 ?
    C19 C20 . 1.358(9) ?
    C19 H19 . 0.93 ?
    C20 C21 . 1.359(8) ?
    C20 H20 . 0.93 ?
    C21 H21 . 0.93 ?
    C22 C23 . 1.373(6) ?
    C22 C30 . 1.421(6) ?
    C23 C24 . 1.420(7) ?
    C23 H23 . 0.93 ?
    C24 C25 . 1.344(8) ?
    C24 H24 . 0.93 ?
    C25 C26 . 1.422(6) ?
    C25 H25 . 0.93 ?
    C26 C27 . 1.405(7) ?
    C26 C30 . 1.415(6) ?
    C27 C28 . 1.354(7) ?
    C27 H27 . 0.93 ?
    C28 C29 . 1.411(6) ?
    C28 H28 . 0.93 ?
    C29 C32 . 1.500(5) ?
    C31 H31A . 0.96 ?
    C31 H31B . 0.96 ?
    C31 H31C . 0.96 ?
    C32 H32A . 0.97 ?
    C32 H32B . 0.97 ?
    C33 C34 . 1.328(6) ?
    C33 H33 . 0.93 ?
    C34 H34 . 0.93 ?
    C35 H35 . 0.93 ?
    C36 C37 . 1.496(6) ?
    C36 H36A . 0.97 ?
    C36 H36B . 0.97 ?
    C37 C42 . 1.357(6) ?
    C37 C38 . 1.363(7) ?
    C38 C39 . 1.396(8) ?
    C38 H38 . 0.93 ?
    C39 C40 . 1.324(9) ?
    C39 H39 . 0.93 ?
    C40 C41 . 1.355(9) ?
    C40 H40 . 0.93 ?
    C41 C42 . 1.371(7) ?
    C41 H41 . 0.93 ?
    C42 H42 . 0.93 ?
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
    F2 P1 F5 . . 178.6(5) ?
    F2 P1 F4 . . 90.3(4) ?
    F5 P1 F4 . . 90.4(4) ?
    F2 P1 F6 . . 89.0(4) ?
    F5 P1 F6 . . 92.3(4) ?
    F4 P1 F6 . . 91.1(3) ?
    F2 P1 F3 . . 91.1(4) ?
    F5 P1 F3 . . 87.6(4) ?
    F4 P1 F3 . . 90.6(4) ?
    F6 P1 F3 . . 178.3(5) ?
    F2 P1 F1 . . 89.4(4) ?
    F5 P1 F1 . . 89.9(4) ?
    F4 P1 F1 . . 179.8(5) ?
    F6 P1 F1 . . 89.0(3) ?
    F3 P1 F1 . . 89.4(4) ?
    F2' P1' F5' . . 177.1(11) ?
    F2' P1' F4' . . 90.7(9) ?
    F5' P1' F4' . . 90.7(8) ?
    F2' P1' F6' . . 87.3(8) ?
    F5' P1' F6' . . 90.1(8) ?
    F4' P1' F6' . . 89.6(8) ?
    F2' P1' F3' . . 89.6(9) ?
    F5' P1' F3' . . 92.9(9) ?
    F4' P1' F3' . . 91.5(9) ?
    F6' P1' F3' . . 176.7(10) ?
    F2' P1' F1' . . 88.5(8) ?
    F5' P1' F1' . . 90.1(8) ?
    F4' P1' F1' . . 178.7(10) ?
    F6' P1' F1' . . 91.3(8) ?
    F3' P1' F1' . . 87.5(9) ?
    F10 P2 F12 . . 90.9(4) ?
    F10 P2 F11 . . 91.0(4) ?
    F12 P2 F11 . . 90.7(4) ?
    F10 P2 F7 . . 178.8(5) ?
    F12 P2 F7 . . 89.3(4) ?
    F11 P2 F7 . . 90.2(4) ?
    F10 P2 F8 . . 90.1(4) ?
    F12 P2 F8 . . 90.3(4) ?
    F11 P2 F8 . . 178.5(5) ?
    F7 P2 F8 . . 88.7(3) ?
    F10 P2 F9 . . 89.2(4) ?
    F12 P2 F9 . . 179.6(5) ?
    F11 P2 F9 . . 89.7(4) ?
    F7 P2 F9 . . 90.6(4) ?
    F8 P2 F9 . . 89.4(4) ?
    F7' P2' F8' . . 90.6(8) ?
    F7' P2' F10' . . 179.2(10) ?
    F8' P2' F10' . . 90.1(8) ?
    F7' P2' F11' . . 91.6(8) ?
    F8' P2' F11' . . 176.9(10) ?
    F10' P2' F11' . . 87.6(8) ?
    F7' P2' F12' . . 88.1(9) ?
    F8' P2' F12' . . 90.9(9) ?
    F10' P2' F12' . . 92.3(9) ?
    F11' P2' F12' . . 91.3(9) ?
    F7' P2' F9' . . 88.6(8) ?
    F8' P2' F9' . . 89.3(8) ?
    F10' P2' F9' . . 91.0(9) ?
    F11' P2' F9' . . 88.7(9) ?
    F12' P2' F9' . . 176.7(10) ?
    C1 O1 C10 . . 117.5(4) ?
    C22 O2 C31 . . 117.4(4) ?
    C8 N1 C9 . . 118.1(4) ?
    C14 N2 C12 . . 107.8(4) ?
    C14 N2 C11 . . 124.9(3) ?
    C12 N2 C11 . . 127.3(4) ?
    C14 N3 C13 . . 108.3(4) ?
    C14 N3 C15 . . 125.9(4) ?
    C13 N3 C15 . . 125.7(4) ?
    C35 N4 C34 . . 107.9(4) ?
    C35 N4 C36 . . 125.9(4) ?
    C34 N4 C36 . . 126.2(4) ?
    C35 N5 C33 . . 107.9(4) ?
    C35 N5 C32 . . 125.4(4) ?
    C33 N5 C32 . . 126.7(4) ?
    C29 N6 C30 . . 118.8(3) ?
    O1 C1 C2 . . 124.8(5) ?
    O1 C1 C9 . . 115.4(4) ?
    C2 C1 C9 . . 119.8(5) ?
    C1 C2 C3 . . 119.7(5) ?
    C1 C2 H2 . . 120.1 ?
    C3 C2 H2 . . 120.1 ?
    C4 C3 C2 . . 121.9(5) ?
    C4 C3 H3 . . 119.1 ?
    C2 C3 H3 . . 119.1 ?
    C3 C4 C5 . . 120.5(5) ?
    C3 C4 H4 . . 119.8 ?
    C5 C4 H4 . . 119.8 ?
    C6 C5 C9 . . 117.6(4) ?
    C6 C5 C4 . . 122.8(5) ?
    C9 C5 C4 . . 119.6(5) ?
    C7 C6 C5 . . 119.5(5) ?
    C7 C6 H6 . . 120.2 ?
    C5 C6 H6 . . 120.2 ?
    C6 C7 C8 . . 118.8(5) ?
    C6 C7 H7 . . 120.6 ?
    C8 C7 H7 . . 120.6 ?
    N1 C8 C7 . . 123.7(4) ?
    N1 C8 C11 . . 116.7(4) ?
    C7 C8 C11 . . 119.6(4) ?
    N1 C9 C5 . . 122.2(4) ?
    N1 C9 C1 . . 119.2(4) ?
    C5 C9 C1 . . 118.5(4) ?
    O1 C10 H10A . . 109.5 ?
    O1 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    O1 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    N2 C11 C8 . . 110.1(3) ?
    N2 C11 H11A . . 109.6 ?
    C8 C11 H11A . . 109.6 ?
    N2 C11 H11B . . 109.6 ?
    C8 C11 H11B . . 109.6 ?
    H11A C11 H11B . . 108.1 ?
    C13 C12 N2 . . 107.7(4) ?
    C13 C12 H12 . . 126.2 ?
    N2 C12 H12 . . 126.2 ?
    C12 C13 N3 . . 107.1(4) ?
    C12 C13 H13 . . 126.4 ?
    N3 C13 H13 . . 126.4 ?
    N3 C14 N2 . . 109.2(3) ?
    N3 C14 H14 . . 125.4 ?
    N2 C14 H14 . . 125.4 ?
    N3 C15 C16 . . 112.6(4) ?
    N3 C15 H15A . . 109.1 ?
    C16 C15 H15A . . 109.1 ?
    N3 C15 H15B . . 109.1 ?
    C16 C15 H15B . . 109.1 ?
    H15A C15 H15B . . 107.8 ?
    C21 C16 C17 . . 119.4(5) ?
    C21 C16 C15 . . 120.3(4) ?
    C17 C16 C15 . . 120.3(4) ?
    C16 C17 C18 . . 120.8(5) ?
    C16 C17 H17 . . 119.6 ?
    C18 C17 H17 . . 119.6 ?
    C19 C18 C17 . . 118.4(6) ?
    C19 C18 H18 . . 120.8 ?
    C17 C18 H18 . . 120.8 ?
    C20 C19 C18 . . 120.2(6) ?
    C20 C19 H19 . . 119.9 ?
    C18 C19 H19 . . 119.9 ?
    C19 C20 C21 . . 121.2(6) ?
    C19 C20 H20 . . 119.4 ?
    C21 C20 H20 . . 119.4 ?
    C20 C21 C16 . . 120.0(5) ?
    C20 C21 H21 . . 120.0 ?
    C16 C21 H21 . . 120.0 ?
    O2 C22 C23 . . 124.3(4) ?
    O2 C22 C30 . . 115.1(3) ?
    C23 C22 C30 . . 120.6(4) ?
    C22 C23 C24 . . 119.5(5) ?
    C22 C23 H23 . . 120.2 ?
    C24 C23 H23 . . 120.2 ?
    C25 C24 C23 . . 121.3(5) ?
    C25 C24 H24 . . 119.3 ?
    C23 C24 H24 . . 119.3 ?
    C24 C25 C26 . . 120.3(5) ?
    C24 C25 H25 . . 119.8 ?
    C26 C25 H25 . . 119.8 ?
    C27 C26 C30 . . 116.8(4) ?
    C27 C26 C25 . . 123.7(5) ?
    C30 C26 C25 . . 119.5(5) ?
    C28 C27 C26 . . 120.7(5) ?
    C28 C27 H27 . . 119.6 ?
    C26 C27 H27 . . 119.6 ?
    C27 C28 C29 . . 118.7(5) ?
    C27 C28 H28 . . 120.6 ?
    C29 C28 H28 . . 120.6 ?
    N6 C29 C28 . . 122.9(4) ?
    N6 C29 C32 . . 116.6(4) ?
    C28 C29 C32 . . 120.4(4) ?
    N6 C30 C26 . . 122.0(4) ?
    N6 C30 C22 . . 119.4(4) ?
    C26 C30 C22 . . 118.6(4) ?
    O2 C31 H31A . . 109.5 ?
    O2 C31 H31B . . 109.5 ?
    H31A C31 H31B . . 109.5 ?
    O2 C31 H31C . . 109.5 ?
    H31A C31 H31C . . 109.5 ?
    H31B C31 H31C . . 109.5 ?
    N5 C32 C29 . . 111.9(3) ?
    N5 C32 H32A . . 109.2 ?
    C29 C32 H32A . . 109.2 ?
    N5 C32 H32B . . 109.2 ?
    C29 C32 H32B . . 109.2 ?
    H32A C32 H32B . . 107.9 ?
    C34 C33 N5 . . 107.6(4) ?
    C34 C33 H33 . . 126.2 ?
    N5 C33 H33 . . 126.2 ?
    C33 C34 N4 . . 107.5(4) ?
    C33 C34 H34 . . 126.3 ?
    N4 C34 H34 . . 126.3 ?
    N5 C35 N4 . . 109.0(4) ?
    N5 C35 H35 . . 125.5 ?
    N4 C35 H35 . . 125.5 ?
    N4 C36 C37 . . 113.2(4) ?
    N4 C36 H36A . . 108.9 ?
    C37 C36 H36A . . 108.9 ?
    N4 C36 H36B . . 108.9 ?
    C37 C36 H36B . . 108.9 ?
    H36A C36 H36B . . 107.8 ?
    C42 C37 C38 . . 117.2(5) ?
    C42 C37 C36 . . 121.3(5) ?
    C38 C37 C36 . . 121.5(5) ?
    C37 C38 C39 . . 120.9(5) ?
    C37 C38 H38 . . 119.5 ?
    C39 C38 H38 . . 119.5 ?
    C40 C39 C38 . . 119.4(6) ?
    C40 C39 H39 . . 120.3 ?
    C38 C39 H39 . . 120.3 ?
    C39 C40 C41 . . 121.6(6) ?
    C39 C40 H40 . . 119.2 ?
    C41 C40 H40 . . 119.2 ?
    C40 C41 C42 . . 118.3(6) ?
    C40 C41 H41 . . 120.8 ?
    C42 C41 H41 . . 120.8 ?
    C37 C42 C41 . . 122.6(5) ?
    C37 C42 H42 . . 118.7 ?
    C41 C42 H42 . . 118.7 ?
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
    C10 O1 C1 C2 . . . . -3.3(9) ?
    C10 O1 C1 C9 . . . . 176.6(6) ?
    O1 C1 C2 C3 . . . . 179.6(5) ?
    C9 C1 C2 C3 . . . . -0.3(8) ?
    C1 C2 C3 C4 . . . . -0.7(10) ?
    C2 C3 C4 C5 . . . . 1.5(10) ?
    C3 C4 C5 C6 . . . . -179.8(6) ?
    C3 C4 C5 C9 . . . . -1.1(8) ?
    C9 C5 C6 C7 . . . . 0.3(7) ?
    C4 C5 C6 C7 . . . . 179.0(5) ?
    C5 C6 C7 C8 . . . . 1.1(8) ?
    C9 N1 C8 C7 . . . . 1.6(6) ?
    C9 N1 C8 C11 . . . . -177.1(3) ?
    C6 C7 C8 N1 . . . . -2.2(7) ?
    C6 C7 C8 C11 . . . . 176.4(4) ?
    C8 N1 C9 C5 . . . . 0.0(6) ?
    C8 N1 C9 C1 . . . . -179.7(4) ?
    C6 C5 C9 N1 . . . . -0.9(7) ?
    C4 C5 C9 N1 . . . . -179.6(4) ?
    C6 C5 C9 C1 . . . . 178.8(4) ?
    C4 C5 C9 C1 . . . . 0.1(7) ?
    O1 C1 C9 N1 . . . . 0.4(6) ?
    C2 C1 C9 N1 . . . . -179.7(4) ?
    O1 C1 C9 C5 . . . . -179.3(4) ?
    C2 C1 C9 C5 . . . . 0.6(7) ?
    C14 N2 C11 C8 . . . . -105.6(4) ?
    C12 N2 C11 C8 . . . . 71.5(5) ?
    N1 C8 C11 N2 . . . . 86.3(4) ?
    C7 C8 C11 N2 . . . . -92.4(5) ?
    C14 N2 C12 C13 . . . . -0.2(5) ?
    C11 N2 C12 C13 . . . . -177.7(4) ?
    N2 C12 C13 N3 . . . . 0.1(5) ?
    C14 N3 C13 C12 . . . . 0.1(5) ?
    C15 N3 C13 C12 . . . . -177.3(4) ?
    C13 N3 C14 N2 . . . . -0.2(5) ?
    C15 N3 C14 N2 . . . . 177.1(3) ?
    C12 N2 C14 N3 . . . . 0.3(5) ?
    C11 N2 C14 N3 . . . . 177.8(3) ?
    C14 N3 C15 C16 . . . . -74.3(5) ?
    C13 N3 C15 C16 . . . . 102.6(5) ?
    N3 C15 C16 C21 . . . . 104.4(5) ?
    N3 C15 C16 C17 . . . . -77.1(6) ?
    C21 C16 C17 C18 . . . . -0.4(8) ?
    C15 C16 C17 C18 . . . . -178.9(5) ?
    C16 C17 C18 C19 . . . . -1.1(10) ?
    C17 C18 C19 C20 . . . . 2.7(11) ?
    C18 C19 C20 C21 . . . . -3.0(10) ?
    C19 C20 C21 C16 . . . . 1.5(9) ?
    C17 C16 C21 C20 . . . . 0.2(8) ?
    C15 C16 C21 C20 . . . . 178.7(5) ?
    C31 O2 C22 C23 . . . . 3.0(6) ?
    C31 O2 C22 C30 . . . . -177.4(4) ?
    O2 C22 C23 C24 . . . . 179.0(4) ?
    C30 C22 C23 C24 . . . . -0.6(6) ?
    C22 C23 C24 C25 . . . . 0.1(7) ?
    C23 C24 C25 C26 . . . . 0.7(8) ?
    C24 C25 C26 C27 . . . . 179.0(5) ?
    C24 C25 C26 C30 . . . . -1.1(7) ?
    C30 C26 C27 C28 . . . . 0.2(7) ?
    C25 C26 C27 C28 . . . . -179.9(5) ?
    C26 C27 C28 C29 . . . . -2.1(8) ?
    C30 N6 C29 C28 . . . . -0.2(6) ?
    C30 N6 C29 C32 . . . . -178.9(3) ?
    C27 C28 C29 N6 . . . . 2.1(7) ?
    C27 C28 C29 C32 . . . . -179.2(4) ?
    C29 N6 C30 C26 . . . . -1.8(5) ?
    C29 N6 C30 C22 . . . . 179.4(3) ?
    C27 C26 C30 N6 . . . . 1.8(6) ?
    C25 C26 C30 N6 . . . . -178.1(4) ?
    C27 C26 C30 C22 . . . . -179.5(4) ?
    C25 C26 C30 C22 . . . . 0.6(6) ?
    O2 C22 C30 N6 . . . . -0.6(5) ?
    C23 C22 C30 N6 . . . . 179.0(3) ?
    O2 C22 C30 C26 . . . . -179.4(3) ?
    C23 C22 C30 C26 . . . . 0.2(5) ?
    C35 N5 C32 C29 . . . . -111.9(4) ?
    C33 N5 C32 C29 . . . . 66.0(6) ?
    N6 C29 C32 N5 . . . . 59.0(5) ?
    C28 C29 C32 N5 . . . . -119.7(4) ?
    C35 N5 C33 C34 . . . . -0.5(5) ?
    C32 N5 C33 C34 . . . . -178.7(4) ?
    N5 C33 C34 N4 . . . . 0.2(5) ?
    C35 N4 C34 C33 . . . . 0.2(5) ?
    C36 N4 C34 C33 . . . . -177.6(4) ?
    C33 N5 C35 N4 . . . . 0.6(5) ?
    C32 N5 C35 N4 . . . . 178.9(3) ?
    C34 N4 C35 N5 . . . . -0.5(5) ?
    C36 N4 C35 N5 . . . . 177.3(4) ?
    C35 N4 C36 C37 . . . . -98.1(5) ?
    C34 N4 C36 C37 . . . . 79.4(6) ?
    N4 C36 C37 C42 . . . . 84.1(6) ?
    N4 C36 C37 C38 . . . . -97.9(6) ?
    C42 C37 C38 C39 . . . . -0.3(8) ?
    C36 C37 C38 C39 . . . . -178.5(5) ?
    C37 C38 C39 C40 . . . . 0.2(9) ?
    C38 C39 C40 C41 . . . . 0.7(10) ?
    C39 C40 C41 C42 . . . . -1.5(11) ?
    C38 C37 C42 C41 . . . . -0.5(9) ?
    C36 C37 C42 C41 . . . . 177.7(6) ?
    C40 C41 C42 C37 . . . . 1.4(11) ?
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
    C11 H11B F6 2_766 0.97 2.53 3.071(7) 115
    C12 H12 F9 1_655 0.93 2.53 3.403(11) 157
    C13 H13 F9 2_665 0.93 2.42 3.341(11) 173
    C14 H14 N1 2_766 0.93 2.38 3.248(5) 156
    C15 H15A F11 2_665 0.97 2.39 3.314(8) 159
    C35 H35 N6 2_657 0.93 2.42 3.343(5) 174
    C36 H36A F8 2_666 0.97 2.52 3.217(8) 129
