##############################################################################
###                                                                        ###
###        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 2.4.    #
#                                                                            #
# 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/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2010-02-18
_journal_date_accepted     2010-02-23
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      3
_journal_page_first     o714
_journal_page_last     o715
_journal_paper_category     QO
_journal_coeditor_code     TK2633
_publ_contact_author_name     'Prof. Fun, Hoong-Kun'
_publ_contact_author_address
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      MALAYSIA
;
_publ_contact_author_email     'hkfun@usm.my'
_publ_contact_author_fax     '604 6579150'
_publ_contact_author_phone     '604 6533652'
_publ_section_title
;
4-(3-Carboxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-7-quinolyl)-1-methylpiperazinium
picrate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Hoong-Kun Fun'
;
      Thomson Reuters ResearcherID: A-3561-2009.
;
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Madhukar Hemamalini' ?
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Divya N. Shetty' ?
;
      Department of Studies in Chemistry
      Mangalore University
      Mangalagangotri 574 199
      India
;
    'B. Narayana' ?
;
      Department of Studies in Chemistry
      Mangalore University
      Mangalagangotri 574 199
      India
;
    'H. S. Yathirajan' ?
;
      Department of Studies in Chemistry
      University of Mysore
      Manasagangotri
      Mysore 570 006
      India
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
4-(3-Carboxy-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-7-quinolyl)-1-methylpiperazinium
picrate
;
_chemical_name_common     'Pefloxacinium picrate'
_chemical_formula_moiety     'C17 H21 F N3 O3 +, C6 H2 N3 O7 -'
_chemical_formula_sum     'C23 H23 F N6 O10'
_chemical_formula_iupac     'C17 H21 F N3 O3 +, C6 H2 N3 O7 -'
_chemical_formula_weight     562.47
_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     7.26450(10)
_cell_length_b     9.1987(2)
_cell_length_c     20.2253(4)
_cell_angle_alpha     77.1160(10)
_cell_angle_beta     81.3150(10)
_cell_angle_gamma     67.1240(10)
_cell_volume     1210.77(4)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     4949
_cell_measurement_theta_min     2.48
_cell_measurement_theta_max     31.75
_cell_measurement_temperature     296
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.36
_exptl_crystal_size_mid     0.13
_exptl_crystal_size_min     0.13
_exptl_crystal_density_diffrn     1.543
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     584
_exptl_absorpt_coefficient_mu     0.128
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2009)'
_exptl_absorpt_correction_T_min     0.9550
_exptl_absorpt_correction_T_max     0.9842
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     296
_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 APEXII CCD area-detector diffractometer
;
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     .
_diffrn_reflns_number     23708
_diffrn_reflns_av_R_equivalents     0.0389
_diffrn_reflns_av_sigmaI/netI     0.0351
_diffrn_reflns_theta_min     2.07
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     27.50
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -26
_diffrn_reflns_limit_l_max     26
_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     5523
_reflns_number_gt     3682
_reflns_threshold_expression     I>2s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0773
_refine_ls_R_factor_gt     0.0465
_refine_ls_wR_factor_gt     0.1067
_refine_ls_wR_factor_ref     0.1227
_refine_ls_goodness_of_fit_ref     1.027
_refine_ls_restrained_S_all     1.027
_refine_ls_number_reflns     5523
_refine_ls_number_parameters     472
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0539P)²+0.1877P] 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     0.209
_refine_diff_density_min     -0.215
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'APEX2 (Bruker, 2009)'
_computing_cell_refinement     'SAINT (Bruker, 2009)'
_computing_data_reduction     'SAINT (Bruker, 2009)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
                             'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
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
    O O1 0.4979(2) 0.79508(17) 0.88294(6) 0.0614(4) Uani d . 1 A .
    O O2 0.7151(13) 0.5178(13) 0.8445(5) 0.067(2) Uani d P 0.56(4) A 1
    O O3 0.9703(16) 0.3754(18) 0.9011(8) 0.075(3) Uani d P 0.56(4) A 1
    O O2B 0.768(5) 0.546(3) 0.8376(7) 0.120(6) Uani d P 0.44(4) A 2
    O O3B 0.934(4) 0.357(3) 0.9074(10) 0.103(5) Uani d P 0.44(4) A 2
    O O4 0.8735(3) 0.32881(19) 1.14260(8) 0.0788(5) Uani d . 1 . .
    O O5 0.6553(3) 0.5215(2) 1.18879(7) 0.0730(5) Uani d . 1 . .
    O O6 0.2844(2) 1.00907(18) 1.04797(8) 0.0663(4) Uani d . 1 . .
    O O7 0.2049(3) 0.9961(2) 0.95255(9) 0.0994(7) Uani d . 1 . .
    N N1 0.8047(2) 0.4832(2) 0.89513(8) 0.0473(4) Uani d . 1 . .
    N N2 0.7383(3) 0.4603(2) 1.13878(9) 0.0543(4) Uani d . 1 . .
    N N3 0.3077(3) 0.9389(2) 1.00085(9) 0.0531(4) Uani d . 1 . .
    C C1 0.7049(2) 0.5634(2) 0.95257(8) 0.0367(4) Uani d . 1 A .
    C C2 0.5487(2) 0.7206(2) 0.94034(8) 0.0388(4) Uani d . 1 . .
    C C3 0.4645(3) 0.7803(2) 1.00324(9) 0.0391(4) Uani d . 1 A .
    C C4 0.5270(3) 0.6985(2) 1.06618(10) 0.0422(4) Uani d . 1 . .
    C C5 0.6760(3) 0.5484(2) 1.07199(9) 0.0425(4) Uani d . 1 A .
    C C6 0.7669(3) 0.4806(2) 1.01542(9) 0.0404(4) Uani d . 1 . .
    F F1 0.63677(18) -0.03326(12) 0.57808(5) 0.0561(3) Uani d . 1 . .
    O O8 -0.0325(3) 0.9171(2) 0.40639(8) 0.0782(5) Uani d . 1 . .
    O O9 0.0924(3) 0.7207(2) 0.34701(8) 0.0711(5) Uani d . 1 . .
    O O10 0.2917(2) 0.43985(18) 0.40332(7) 0.0611(4) Uani d . 1 . .
    N N4 0.2108(2) 0.60713(17) 0.58140(7) 0.0395(3) Uani d . 1 . .
    N N5 0.5335(2) 0.06173(16) 0.70402(7) 0.0355(3) Uani d . 1 . .
    N N6 0.2153(2) 0.01715(17) 0.80261(7) 0.0381(3) Uani d . 1 . .
    C C7 0.1335(3) 0.7054(2) 0.52424(10) 0.0452(5) Uani d . 1 . .
    C C8 0.1526(3) 0.6553(2) 0.46406(9) 0.0456(5) Uani d . 1 . .
    C C9 0.2625(3) 0.4915(2) 0.45840(9) 0.0440(5) Uani d . 1 . .
    C C10 0.3409(3) 0.3855(2) 0.52080(8) 0.0375(4) Uani d . 1 . .
    C C11 0.4521(3) 0.2212(2) 0.52173(9) 0.0419(4) Uani d . 1 . .
    C C12 0.5179(3) 0.1222(2) 0.58059(9) 0.0386(4) Uani d . 1 . .
    C C13 0.4736(2) 0.1723(2) 0.64432(8) 0.0329(4) Uani d . 1 . .
    C C14 0.3771(2) 0.3363(2) 0.64216(9) 0.0341(4) Uani d . 1 . .
    C C15 0.3112(2) 0.4432(2) 0.58177(8) 0.0343(4) Uani d . 1 . .
    C C16 0.4921(3) -0.0875(2) 0.71661(10) 0.0403(4) Uani d . 1 . .
    C C17 0.2763(3) -0.0593(2) 0.74081(9) 0.0403(4) Uani d . 1 . .
    C C18 0.2690(3) 0.1625(2) 0.79291(10) 0.0409(4) Uani d . 1 . .
    C C19 0.4868(3) 0.1236(2) 0.76759(9) 0.0386(4) Uani d . 1 . .
    C C20 -0.0031(3) 0.0581(3) 0.82167(14) 0.0571(6) Uani d . 1 . .
    C C21 0.1823(3) 0.6765(3) 0.64328(11) 0.0493(5) Uani d . 1 . .
    C C22 0.0028(4) 0.6633(4) 0.68827(13) 0.0664(7) Uani d . 1 . .
    C C23 0.0618(3) 0.7773(3) 0.40435(11) 0.0563(6) Uani d . 1 . .
    H H4 0.468(3) 0.743(2) 1.1031(11) 0.055(6) Uiso d . 1 . .
    H H6 0.864(3) 0.386(2) 1.0177(9) 0.046(5) Uiso d . 1 . .
    H H7 0.066(3) 0.813(3) 0.5297(10) 0.055(6) Uiso d . 1 . .
    H H11 0.485(3) 0.181(2) 0.4813(10) 0.047(5) Uiso d . 1 . .
    H H14 0.349(2) 0.379(2) 0.6821(9) 0.036(5) Uiso d . 1 . .
    H H16A 0.526(3) -0.136(2) 0.6761(11) 0.057(6) Uiso d . 1 . .
    H H16B 0.583(3) -0.163(2) 0.7505(10) 0.053(5) Uiso d . 1 . .
    H H17A 0.193(3) 0.012(2) 0.7078(9) 0.044(5) Uiso d . 1 . .
    H H17B 0.251(3) -0.164(3) 0.7550(10) 0.059(6) Uiso d . 1 . .
    H H18A 0.245(3) 0.196(2) 0.8351(10) 0.043(5) Uiso d . 1 . .
    H H18B 0.182(3) 0.241(2) 0.7603(10) 0.045(5) Uiso d . 1 . .
    H H19A 0.569(3) 0.039(2) 0.8001(9) 0.040(5) Uiso d . 1 . .
    H H19B 0.521(2) 0.220(2) 0.7621(9) 0.040(5) Uiso d . 1 . .
    H H20A -0.038(3) 0.107(3) 0.8617(12) 0.072(7) Uiso d . 1 . .
    H H20B -0.079(4) 0.131(3) 0.7848(13) 0.081(8) Uiso d . 1 . .
    H H20C -0.033(3) -0.043(3) 0.8318(12) 0.080(8) Uiso d . 1 . .
    H H21A 0.303(3) 0.623(2) 0.6670(9) 0.046(5) Uiso d . 1 . .
    H H21B 0.161(3) 0.781(3) 0.6285(10) 0.055(6) Uiso d . 1 . .
    H H22A -0.106(4) 0.710(3) 0.6634(14) 0.096(9) Uiso d . 1 . .
    H H22B 0.022(4) 0.552(4) 0.7065(13) 0.092(9) Uiso d . 1 . .
    H H22C -0.013(4) 0.715(3) 0.7274(15) 0.103(9) Uiso d . 1 . .
    H H1O9 0.179(4) 0.610(4) 0.3556(15) 0.110(11) Uiso d . 1 . .
    H H1N6 0.284(3) -0.055(2) 0.8372(10) 0.044(5) Uiso d . 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
    O1 C2 . 1.2375(19) ?
    O2 N1 . 1.212(8) ?
    O3 N1 . 1.228(13) ?
    O2B N1 . 1.196(13) ?
    O3B N1 . 1.177(17) ?
    O4 N2 . 1.221(2) ?
    O5 N2 . 1.229(2) ?
    O6 N3 . 1.222(2) ?
    O7 N3 . 1.214(2) ?
    N1 C1 . 1.460(2) ?
    N2 C5 . 1.448(2) ?
    N3 C3 . 1.457(2) ?
    C1 C6 . 1.368(2) ?
    C1 C2 . 1.446(2) ?
    C2 C3 . 1.452(2) ?
    C3 C4 . 1.369(2) ?
    C4 C5 . 1.377(3) ?
    C4 H4 . 0.90(2) ?
    C5 C6 . 1.380(3) ?
    C6 H6 . 0.882(19) ?
    F1 C12 . 1.3609(19) ?
    O8 C23 . 1.206(3) ?
    O9 C23 . 1.329(3) ?
    O9 H1O9 . 0.96(3) ?
    O10 C9 . 1.264(2) ?
    N4 C7 . 1.343(2) ?
    N4 C15 . 1.396(2) ?
    N4 C21 . 1.480(2) ?
    N5 C13 . 1.396(2) ?
    N5 C19 . 1.462(2) ?
    N5 C16 . 1.477(2) ?
    N6 C20 . 1.491(2) ?
    N6 C17 . 1.496(2) ?
    N6 C18 . 1.498(2) ?
    N6 H1N6 . 0.905(19) ?
    C7 C8 . 1.365(3) ?
    C7 H7 . 0.94(2) ?
    C8 C9 . 1.426(3) ?
    C8 C23 . 1.488(3) ?
    C9 C10 . 1.451(2) ?
    C10 C15 . 1.404(2) ?
    C10 C11 . 1.407(3) ?
    C11 C12 . 1.351(2) ?
    C11 H11 . 0.932(19) ?
    C12 C13 . 1.415(2) ?
    C13 C14 . 1.388(2) ?
    C14 C15 . 1.401(2) ?
    C14 H14 . 0.936(17) ?
    C16 C17 . 1.508(3) ?
    C16 H16A . 0.97(2) ?
    C16 H16B . 0.98(2) ?
    C17 H17A . 0.929(19) ?
    C17 H17B . 1.02(2) ?
    C18 C19 . 1.514(3) ?
    C18 H18A . 0.942(19) ?
    C18 H18B . 0.956(19) ?
    C19 H19A . 0.959(18) ?
    C19 H19B . 0.994(18) ?
    C20 H20A . 0.97(2) ?
    C20 H20B . 0.96(3) ?
    C20 H20C . 1.01(3) ?
    C21 C22 . 1.502(3) ?
    C21 H21A . 0.964(19) ?
    C21 H21B . 0.90(2) ?
    C22 H22A . 0.91(3) ?
    C22 H22B . 0.97(3) ?
    C22 H22C . 0.98(3) ?
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
    O3B N1 O2B . . 120.7(12) ?
    O3B N1 O2 . . 119.9(11) ?
    O2B N1 O2 . . 25.4(19) ?
    O3B N1 O3 . . 17.2(18) ?
    O2B N1 O3 . . 114.2(11) ?
    O2 N1 O3 . . 121.9(8) ?
    O3B N1 C1 . . 116.8(10) ?
    O2B N1 C1 . . 122.4(7) ?
    O2 N1 C1 . . 118.6(5) ?
    O3 N1 C1 . . 119.3(7) ?
    O4 N2 O5 . . 122.98(17) ?
    O4 N2 C5 . . 118.14(18) ?
    O5 N2 C5 . . 118.87(17) ?
    O7 N3 O6 . . 122.52(18) ?
    O7 N3 C3 . . 119.07(17) ?
    O6 N3 C3 . . 118.41(17) ?
    C6 C1 C2 . . 124.48(16) ?
    C6 C1 N1 . . 116.28(16) ?
    C2 C1 N1 . . 119.24(15) ?
    O1 C2 C1 . . 123.51(16) ?
    O1 C2 C3 . . 124.90(16) ?
    C1 C2 C3 . . 111.58(14) ?
    C4 C3 C2 . . 124.16(16) ?
    C4 C3 N3 . . 116.38(16) ?
    C2 C3 N3 . . 119.44(15) ?
    C3 C4 C5 . . 119.36(18) ?
    C3 C4 H4 . . 119.3(13) ?
    C5 C4 H4 . . 121.4(13) ?
    C4 C5 C6 . . 121.23(16) ?
    C4 C5 N2 . . 119.28(18) ?
    C6 C5 N2 . . 119.49(17) ?
    C1 C6 C5 . . 119.18(17) ?
    C1 C6 H6 . . 117.8(12) ?
    C5 C6 H6 . . 123.0(12) ?
    C23 O9 H1O9 . . 108.0(18) ?
    C7 N4 C15 . . 119.85(16) ?
    C7 N4 C21 . . 118.47(16) ?
    C15 N4 C21 . . 121.66(14) ?
    C13 N5 C19 . . 117.44(14) ?
    C13 N5 C16 . . 118.83(14) ?
    C19 N5 C16 . . 108.08(14) ?
    C20 N6 C17 . . 110.80(17) ?
    C20 N6 C18 . . 110.72(16) ?
    C17 N6 C18 . . 111.68(14) ?
    C20 N6 H1N6 . . 108.7(11) ?
    C17 N6 H1N6 . . 107.7(11) ?
    C18 N6 H1N6 . . 107.1(12) ?
    N4 C7 C8 . . 123.61(19) ?
    N4 C7 H7 . . 113.1(12) ?
    C8 C7 H7 . . 123.3(12) ?
    C7 C8 C9 . . 120.63(16) ?
    C7 C8 C23 . . 118.05(19) ?
    C9 C8 C23 . . 121.28(19) ?
    O10 C9 C8 . . 123.29(16) ?
    O10 C9 C10 . . 121.36(18) ?
    C8 C9 C10 . . 115.36(17) ?
    C15 C10 C11 . . 117.85(15) ?
    C15 C10 C9 . . 121.42(17) ?
    C11 C10 C9 . . 120.73(16) ?
    C12 C11 C10 . . 120.33(17) ?
    C12 C11 H11 . . 119.8(12) ?
    C10 C11 H11 . . 119.8(12) ?
    C11 C12 F1 . . 118.09(16) ?
    C11 C12 C13 . . 123.53(16) ?
    F1 C12 C13 . . 118.36(14) ?
    C14 C13 N5 . . 123.69(15) ?
    C14 C13 C12 . . 115.50(15) ?
    N5 C13 C12 . . 120.75(15) ?
    C13 C14 C15 . . 122.18(16) ?
    C13 C14 H14 . . 120.3(11) ?
    C15 C14 H14 . . 117.5(11) ?
    N4 C15 C14 . . 120.91(15) ?
    N4 C15 C10 . . 118.98(14) ?
    C14 C15 C10 . . 120.08(16) ?
    N5 C16 C17 . . 111.86(15) ?
    N5 C16 H16A . . 111.3(12) ?
    C17 C16 H16A . . 109.6(12) ?
    N5 C16 H16B . . 106.4(11) ?
    C17 C16 H16B . . 111.3(11) ?
    H16A C16 H16B . . 106.2(16) ?
    N6 C17 C16 . . 111.76(15) ?
    N6 C17 H17A . . 105.8(11) ?
    C16 C17 H17A . . 110.2(11) ?
    N6 C17 H17B . . 105.1(11) ?
    C16 C17 H17B . . 112.0(11) ?
    H17A C17 H17B . . 111.7(16) ?
    N6 C18 C19 . . 110.49(15) ?
    N6 C18 H18A . . 107.9(11) ?
    C19 C18 H18A . . 110.3(11) ?
    N6 C18 H18B . . 105.3(11) ?
    C19 C18 H18B . . 111.5(11) ?
    H18A C18 H18B . . 111.3(16) ?
    N5 C19 C18 . . 112.19(14) ?
    N5 C19 H19A . . 105.6(10) ?
    C18 C19 H19A . . 108.9(10) ?
    N5 C19 H19B . . 110.7(10) ?
    C18 C19 H19B . . 109.8(10) ?
    H19A C19 H19B . . 109.6(14) ?
    N6 C20 H20A . . 108.9(14) ?
    N6 C20 H20B . . 109.9(14) ?
    H20A C20 H20B . . 110(2) ?
    N6 C20 H20C . . 109.0(14) ?
    H20A C20 H20C . . 110(2) ?
    H20B C20 H20C . . 109.3(19) ?
    N4 C21 C22 . . 112.15(19) ?
    N4 C21 H21A . . 108.2(11) ?
    C22 C21 H21A . . 111.4(11) ?
    N4 C21 H21B . . 105.7(13) ?
    C22 C21 H21B . . 108.4(13) ?
    H21A C21 H21B . . 110.9(17) ?
    C21 C22 H22A . . 108.4(17) ?
    C21 C22 H22B . . 110.9(15) ?
    H22A C22 H22B . . 110(2) ?
    C21 C22 H22C . . 109.2(17) ?
    H22A C22 H22C . . 112(2) ?
    H22B C22 H22C . . 107(2) ?
    O8 C23 O9 . . 121.43(19) ?
    O8 C23 C8 . . 123.9(2) ?
    O9 C23 C8 . . 114.6(2) ?
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
    O3B N1 C1 C6 . . . . -2.1(18) ?
    O2B N1 C1 C6 . . . . -177(2) ?
    O2 N1 C1 C6 . . . . 153.5(6) ?
    O3 N1 C1 C6 . . . . -21.4(8) ?
    O3B N1 C1 C2 . . . . 178.6(18) ?
    O2B N1 C1 C2 . . . . 3(2) ?
    O2 N1 C1 C2 . . . . -25.9(6) ?
    O3 N1 C1 C2 . . . . 159.2(7) ?
    C6 C1 C2 O1 . . . . 178.26(18) ?
    N1 C1 C2 O1 . . . . -2.5(3) ?
    C6 C1 C2 C3 . . . . -0.2(2) ?
    N1 C1 C2 C3 . . . . 179.05(15) ?
    O1 C2 C3 C4 . . . . -177.76(18) ?
    C1 C2 C3 C4 . . . . 0.7(2) ?
    O1 C2 C3 N3 . . . . 0.3(3) ?
    C1 C2 C3 N3 . . . . 178.69(15) ?
    O7 N3 C3 C4 . . . . -157.8(2) ?
    O6 N3 C3 C4 . . . . 21.9(2) ?
    O7 N3 C3 C2 . . . . 24.0(3) ?
    O6 N3 C3 C2 . . . . -156.28(17) ?
    C2 C3 C4 C5 . . . . -1.4(3) ?
    N3 C3 C4 C5 . . . . -179.47(16) ?
    C3 C4 C5 C6 . . . . 1.6(3) ?
    C3 C4 C5 N2 . . . . -178.45(16) ?
    O4 N2 C5 C4 . . . . -178.56(18) ?
    O5 N2 C5 C4 . . . . 0.5(3) ?
    O4 N2 C5 C6 . . . . 1.4(3) ?
    O5 N2 C5 C6 . . . . -179.54(17) ?
    C2 C1 C6 C5 . . . . 0.5(3) ?
    N1 C1 C6 C5 . . . . -178.80(15) ?
    C4 C5 C6 C1 . . . . -1.2(3) ?
    N2 C5 C6 C1 . . . . 178.90(16) ?
    C15 N4 C7 C8 . . . . -2.3(3) ?
    C21 N4 C7 C8 . . . . 179.16(17) ?
    N4 C7 C8 C9 . . . . -1.3(3) ?
    N4 C7 C8 C23 . . . . -179.19(17) ?
    C7 C8 C9 O10 . . . . -177.07(17) ?
    C23 C8 C9 O10 . . . . 0.7(3) ?
    C7 C8 C9 C10 . . . . 2.8(2) ?
    C23 C8 C9 C10 . . . . -179.41(16) ?
    O10 C9 C10 C15 . . . . 179.02(15) ?
    C8 C9 C10 C15 . . . . -0.8(2) ?
    O10 C9 C10 C11 . . . . -0.1(3) ?
    C8 C9 C10 C11 . . . . -179.94(16) ?
    C15 C10 C11 C12 . . . . 3.5(3) ?
    C9 C10 C11 C12 . . . . -177.41(16) ?
    C10 C11 C12 F1 . . . . -175.41(15) ?
    C10 C11 C12 C13 . . . . 3.1(3) ?
    C19 N5 C13 C14 . . . . 1.4(2) ?
    C16 N5 C13 C14 . . . . 134.68(17) ?
    C19 N5 C13 C12 . . . . 178.36(15) ?
    C16 N5 C13 C12 . . . . -48.4(2) ?
    C11 C12 C13 C14 . . . . -7.6(2) ?
    F1 C12 C13 C14 . . . . 170.87(14) ?
    C11 C12 C13 N5 . . . . 175.20(16) ?
    F1 C12 C13 N5 . . . . -6.3(2) ?
    N5 C13 C14 C15 . . . . -177.14(15) ?
    C12 C13 C14 C15 . . . . 5.8(2) ?
    C7 N4 C15 C14 . . . . -174.14(15) ?
    C21 N4 C15 C14 . . . . 4.4(2) ?
    C7 N4 C15 C10 . . . . 4.2(2) ?
    C21 N4 C15 C10 . . . . -177.34(16) ?
    C13 C14 C15 N4 . . . . 178.65(15) ?
    C13 C14 C15 C10 . . . . 0.4(2) ?
    C11 C10 C15 N4 . . . . 176.55(15) ?
    C9 C10 C15 N4 . . . . -2.6(2) ?
    C11 C10 C15 C14 . . . . -5.1(2) ?
    C9 C10 C15 C14 . . . . 175.75(15) ?
    C13 N5 C16 C17 . . . . -77.71(19) ?
    C19 N5 C16 C17 . . . . 59.43(18) ?
    C20 N6 C17 C16 . . . . 174.57(16) ?
    C18 N6 C17 C16 . . . . 50.64(19) ?
    N5 C16 C17 N6 . . . . -55.40(19) ?
    C20 N6 C18 C19 . . . . -175.03(17) ?
    C17 N6 C18 C19 . . . . -51.05(19) ?
    C13 N5 C19 C18 . . . . 77.00(19) ?
    C16 N5 C19 C18 . . . . -60.83(18) ?
    N6 C18 C19 N5 . . . . 57.51(19) ?
    C7 N4 C21 C22 . . . . 94.7(2) ?
    C15 N4 C21 C22 . . . . -83.8(2) ?
    C7 C8 C23 O8 . . . . -2.2(3) ?
    C9 C8 C23 O8 . . . . 179.97(19) ?
    C7 C8 C23 O9 . . . . 177.75(17) ?
    C9 C8 C23 O9 . . . . -0.1(3) ?
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
    _geom_hbond_publ_flag
    O9 H1O9 O10 . 0.96(3) 1.62(3) 2.519(2) 155(3) yes
    N6 H1N6 O1 1_545 0.91(2) 1.84(2) 2.701(2) 159(2) yes
    N6 H1N6 O7 1_545 0.91(2) 2.422(19) 2.987(2) 120.6(15) yes
    C6 H6 O3 . 0.878(19) 2.38(2) 2.706(16) 102.3(14) yes
    C11 H11 F1 2_656 0.933(19) 2.46(2) 3.209(2) 137.3(18) yes
    C16 H16A F1 . 0.97(2) 2.18(2) 2.846(2) 124.6(15) yes
    C17 H17A O8 2_566 0.928(19) 2.582(19) 3.430(3) 152.2(14) yes
    C17 H17B O4 2_657 1.02(2) 2.55(2) 3.407(3) 141.2(16) yes
    C18 H18A O3 1_455 0.940(19) 2.47(2) 3.241(16) 139.2(18) yes
    C19 H19B O5 2_667 0.990(17) 2.566(17) 3.300(2) 131.0(13) yes
    C20 H20A O7 1_545 0.97(2) 2.51(2) 3.079(3) 118.0(18) yes
    C20 H20C O4 2_657 1.01(3) 2.39(3) 3.245(3) 141.8(19) yes
    C21 H21B O8 2_576 0.90(3) 2.53(3) 3.415(3) 169(2) yes
