##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
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# of the IUCr Commission on Journals.                                        #
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#                                                                            #
# 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  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-12-27
_journal_date_accepted     2011-01-11
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue      2
_journal_page_first     o432
_journal_page_last     o433
_journal_paper_category     QO
_journal_coeditor_code     BT5451
_publ_contact_author_name     'Jasinski, Jerry P.'
_publ_contact_author_address
;
Department of Chemistry
Keene State College
229 Main Street
Keene, New Hampshire 03435, USA
;
_publ_contact_author_email     jjasinski@keene.edu
_publ_contact_author_fax     ?
_publ_contact_author_phone     '603 358-2563'
_publ_section_title
;
Enrofloxacinium picrate
;
loop_
    _publ_author_name
    _publ_author_address
    'Jasinski, Jerry P.'
;
Department of Chemistry
Keene State College
229 Main Street
Keene, NH 03435-2001, USA
;
    'Butcher, Ray J.'
;
Department of Chemistry
Howard University
525 College Street NW
Washington
DC 20059, USA
;
    'Siddegowda, M. S.'
;
Department of Studies in Chemistry
University of Mysore
Manasagangotri, Mysore 570 006, India
;
    'Yathirajan, H. S.'
;
Department of Studies in Chemistry
University of Mysore
Manasagangotri, Mysore 570 006, India
;
    'Siddaraju, B. P.'
;
Department of Studies in Chemistry
University of Mysore
Manasagangotri, Mysore 570 006, India
;
data_I
_chemical_name_systematic
;
4-(3-carboxy-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)-1-ethylpiperazin-1-ium
2,4,6-trinitrophenolate
;
_chemical_name_common     'Enrofloxacinium picrate'
_chemical_formula_moiety     'C19 H23 F N3 O3 +, C6 H2 N3 O7 -'
_chemical_formula_sum     'C25 H25 F N6 O10'
_chemical_formula_iupac     'C19 H23 F N3 O3 +, C6 H2 N3 O7 -'
_chemical_formula_weight     588.51
_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     7.2111(7)
_cell_length_b     12.5766(7)
_cell_length_c     16.2362(4)
_cell_angle_alpha     105.556(2)
_cell_angle_beta     96.367(6)
_cell_angle_gamma     96.223(7)
_cell_volume     1395.04(16)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2958
_cell_measurement_theta_min     5.2649
_cell_measurement_theta_max     73.4307
_cell_measurement_temperature     295(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     'pale yellow'
_exptl_crystal_size_max     0.44
_exptl_crystal_size_mid     0.31
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.401
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     612
_exptl_absorpt_coefficient_mu     0.981
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2007)
;
_exptl_absorpt_correction_T_min     0.89570
_exptl_absorpt_correction_T_max     1.00000
_exptl_special_details
;
;
_diffrn_ambient_temperature     295(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_source     'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Oxford Diffraction Xcalibur Ruby Gemini'
_diffrn_measurement_method     \w
_diffrn_detector_area_resol_mean     10.5081
_diffrn_reflns_number     9440
_diffrn_reflns_av_R_equivalents     0.0321
_diffrn_reflns_av_sigmaI/netI     0.0436
_diffrn_reflns_theta_min     5.27
_diffrn_reflns_theta_max     73.59
_diffrn_reflns_theta_full     67.50
_diffrn_measured_fraction_theta_max     0.967
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -5
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     20
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted <i>R</i>-factor
<i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i>^2^, conventional
<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
negative <i>F</i>^2^. The threshold expression of <i>F</i>^2^ >
\s(<i>F</i>^2^) is used only for calculating <i>R</i>-factors(gt) <i>etc</i>.
and is not relevant to the choice of reflections for refinement.
<i>R</i>-factors based on <i>F</i>^2^ are statistically about twice as large
as those based on <i>F</i>, and <i>R</i>- factors based on ALL data will be
even larger.
;
_reflns_number_total     5437
_reflns_number_gt     3425
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0817
_refine_ls_R_factor_gt     0.0553
_refine_ls_wR_factor_gt     0.1568
_refine_ls_wR_factor_ref     0.1774
_refine_ls_goodness_of_fit_ref     0.996
_refine_ls_restrained_S_all     0.996
_refine_ls_number_reflns     5437
_refine_ls_number_parameters     382
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[\s^2^(Fo^2^)+(0.0924P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.204
_refine_diff_density_min     -0.196
_refine_ls_extinction_method     '<i>SHELXL97</i> (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0007(4)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-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' 0.0181 0.0091
                         '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' 0.0311 0.0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'F' 'F' 0.0727 0.0534
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     '<i>CrysAlis PRO</i> (Oxford Diffraction, 2007)'
_computing_cell_refinement     '<i>CrysAlis PRO</i> (Oxford Diffraction, 2007)'
_computing_data_reduction     '<i>CrysAlis RED</i> (Oxford Diffraction, 2007)'
_computing_structure_solution     '<i>SHELXS97</i> (Sheldrick, 2008)'
_computing_structure_refinement     '<i>SHELXL97</i> (Sheldrick, 2008)'
_computing_molecular_graphics     '<i>SHELXTL</i> (Sheldrick, 2008)'
_computing_publication_material     '<i>SHELXTL</i> (Sheldrick, 2008)'
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
    F F1 0.0392(3) 0.14397(14) 0.02905(11) 0.0785(5) Uani d . 1 . .
    O O1 0.4038(4) 0.7253(2) -0.10088(16) 0.0920(8) Uani d . 1 . .
    O O2 0.3085(3) 0.5648(2) -0.19916(12) 0.0747(6) Uani d . 1 . .
    H H2 0.2552 0.5031 -0.2008 0.112 Uiso calc R 1 . .
    O O3 0.2077(3) 0.39341(17) -0.15203(11) 0.0611(5) Uani d . 1 . .
    N N1 0.2699(3) 0.59410(17) 0.09706(12) 0.0456(5) Uani d . 1 . .
    N N2 0.0978(3) 0.27232(19) 0.20117(14) 0.0580(6) Uani d . 1 . .
    N N3 0.3999(3) 0.2675(2) 0.33307(14) 0.0591(6) Uani d . 1 . .
    H H3A 0.3366 0.2332 0.3665 0.071 Uiso calc R 1 . .
    C C1 0.1315(3) 0.3205(2) 0.13528(16) 0.0490(6) Uani d . 1 . .
    C C2 0.1818(3) 0.4344(2) 0.14892(15) 0.0460(5) Uani d . 1 . .
    H H2A 0.1934 0.4819 0.2046 0.055 Uiso calc R 1 . .
    C C3 0.2153(3) 0.47948(19) 0.08107(13) 0.0405(5) Uani d . 1 . .
    C C4 0.3062(3) 0.6357(2) 0.03193(15) 0.0465(5) Uani d . 1 . .
    H H4A 0.3420 0.7123 0.0444 0.056 Uiso calc R 1 . .
    C C5 0.2938(3) 0.5723(2) -0.05229(15) 0.0469(5) Uani d . 1 . .
    C C6 0.3401(4) 0.6293(3) -0.11816(18) 0.0617(7) Uani d . 1 . .
    C C7 0.2321(3) 0.4553(2) -0.07435(14) 0.0465(5) Uani d . 1 . .
    C C8 0.1951(3) 0.4099(2) -0.00384(14) 0.0448(5) Uani d . 1 . .
    C C9 0.1368(3) 0.2958(2) -0.01881(16) 0.0510(6) Uani d . 1 . .
    H H9A 0.1199 0.2484 -0.0748 0.061 Uiso calc R 1 . .
    C C10 0.1051(4) 0.2543(2) 0.04762(17) 0.0553(6) Uani d . 1 . .
    C C11 0.2678(4) 0.6702(2) 0.18217(16) 0.0519(6) Uani d . 1 . .
    H H11A 0.1420 0.6815 0.1971 0.062 Uiso calc R 1 . .
    C C12 0.4138(4) 0.6777(3) 0.25637(18) 0.0645(7) Uani d . 1 . .
    H H12A 0.3750 0.6903 0.3131 0.077 Uiso calc R 1 . .
    H H12B 0.5118 0.6306 0.2463 0.077 Uiso calc R 1 . .
    C C13 0.4137(5) 0.7695(3) 0.2158(2) 0.0735(8) Uani d . 1 . .
    H H13A 0.5119 0.7788 0.1810 0.088 Uiso calc R 1 . .
    H H13B 0.3752 0.8384 0.2478 0.088 Uiso calc R 1 . .
    C C14 0.1708(5) 0.1684(3) 0.2041(2) 0.0691(8) Uani d . 1 . .
    H H14A 0.1588 0.1193 0.1458 0.083 Uiso calc R 1 . .
    H H14B 0.0958 0.1309 0.2368 0.083 Uiso calc R 1 . .
    C C15 0.3727(4) 0.1898(3) 0.24448(18) 0.0639(7) Uani d . 1 . .
    H H15A 0.4143 0.1198 0.2470 0.077 Uiso calc R 1 . .
    H H15B 0.4494 0.2213 0.2090 0.077 Uiso calc R 1 . .
    C C16 0.3177(5) 0.3719(2) 0.33310(18) 0.0650(7) Uani d . 1 . .
    H H16A 0.3916 0.4147 0.3034 0.078 Uiso calc R 1 . .
    H H16B 0.3222 0.4172 0.3921 0.078 Uiso calc R 1 . .
    C C17 0.1147(4) 0.3434(3) 0.28845(17) 0.0612(7) Uani d . 1 . .
    H H17A 0.0393 0.3063 0.3213 0.073 Uiso calc R 1 . .
    H H17B 0.0651 0.4118 0.2874 0.073 Uiso calc R 1 . .
    C C18 0.6053(5) 0.2905(4) 0.3705(3) 0.0917(11) Uani d . 1 . .
    H H18A 0.6582 0.2213 0.3560 0.110 Uiso calc R 1 . .
    H H18B 0.6707 0.3413 0.3441 0.110 Uiso calc R 1 . .
    C C19 0.6391(7) 0.3390(4) 0.4650(3) 0.1301(18) Uani d . 1 . .
    H H19A 0.7709 0.3660 0.4836 0.195 Uiso calc R 1 . .
    H H19B 0.6006 0.2830 0.4923 0.195 Uiso calc R 1 . .
    H H19C 0.5677 0.3997 0.4807 0.195 Uiso calc R 1 . .
    O O1A 0.1749(3) 0.2238(2) 0.44767(13) 0.0791(7) Uani d . 1 . .
    O O2A 0.1956(6) 0.4178(2) 0.5795(2) 0.1384(15) Uani d . 1 . .
    O O3A -0.0251(4) 0.3840(2) 0.64871(17) 0.0934(8) Uani d . 1 . .
    O O4A 0.0864(4) 0.0906(2) 0.78322(15) 0.0947(8) Uani d . 1 . .
    O O5A 0.2090(4) -0.0501(2) 0.71552(16) 0.0919(8) Uani d . 1 . .
    O O6A 0.3078(3) -0.09139(19) 0.42732(14) 0.0761(6) Uani d . 1 . .
    O O7A 0.3468(4) 0.0487(2) 0.37754(15) 0.0939(8) Uani d . 1 . .
    N N1A 0.0996(4) 0.3558(2) 0.60751(17) 0.0724(7) Uani d . 1 . .
    N N2A 0.1542(4) 0.0399(2) 0.72150(14) 0.0640(6) Uani d . 1 . .
    N N3A 0.2989(3) 0.0068(2) 0.43254(14) 0.0594(6) Uani d . 1 . .
    C C1A 0.1855(3) 0.1834(2) 0.50984(16) 0.0528(6) Uani d . 1 . .
    C C2A 0.1375(4) 0.2406(2) 0.59322(17) 0.0531(6) Uani d . 1 . .
    C C3A 0.1247(4) 0.1958(2) 0.65942(16) 0.0526(6) Uani d . 1 . .
    H H3AA 0.0879 0.2362 0.7103 0.063 Uiso calc R 1 . .
    C C4A 0.1673(3) 0.0878(2) 0.65059(15) 0.0494(6) Uani d . 1 . .
    C C5A 0.2252(3) 0.0292(2) 0.57639(16) 0.0489(5) Uani d . 1 . .
    H H5AA 0.2573 -0.0416 0.5717 0.059 Uiso calc R 1 . .
    C C6A 0.2361(3) 0.0748(2) 0.50884(15) 0.0486(6) Uani d . 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    F1 0.1083(14) 0.0580(10) 0.0638(11) -0.0030(9) 0.0032(9) 0.0181(8)
    O1 0.129(2) 0.0800(16) 0.0781(15) -0.0007(15) 0.0328(14) 0.0403(13)
    O2 0.0854(14) 0.1032(17) 0.0458(11) 0.0184(12) 0.0220(9) 0.0319(10)
    O3 0.0700(11) 0.0758(12) 0.0350(9) 0.0115(9) 0.0124(8) 0.0093(8)
    N1 0.0441(10) 0.0565(12) 0.0375(10) 0.0120(9) 0.0084(8) 0.0128(8)
    N2 0.0635(13) 0.0660(14) 0.0527(12) 0.0125(11) 0.0111(10) 0.0286(11)
    N3 0.0636(13) 0.0714(15) 0.0543(13) 0.0129(11) 0.0117(10) 0.0358(11)
    C1 0.0479(12) 0.0589(15) 0.0458(13) 0.0112(11) 0.0087(10) 0.0224(11)
    C2 0.0479(12) 0.0560(14) 0.0356(11) 0.0150(10) 0.0049(9) 0.0130(10)
    C3 0.0372(10) 0.0521(13) 0.0344(10) 0.0139(9) 0.0058(8) 0.0131(9)
    C4 0.0425(11) 0.0555(14) 0.0456(13) 0.0111(10) 0.0099(9) 0.0182(10)
    C5 0.0433(12) 0.0630(15) 0.0403(12) 0.0147(11) 0.0100(9) 0.0200(11)
    C6 0.0618(16) 0.084(2) 0.0526(15) 0.0217(15) 0.0219(12) 0.0319(14)
    C7 0.0368(11) 0.0665(15) 0.0392(12) 0.0155(10) 0.0083(9) 0.0157(11)
    C8 0.0400(11) 0.0586(14) 0.0383(11) 0.0161(10) 0.0055(9) 0.0147(10)
    C9 0.0544(13) 0.0554(14) 0.0408(12) 0.0149(11) 0.0044(10) 0.0077(10)
    C10 0.0579(14) 0.0553(15) 0.0515(14) 0.0071(12) 0.0039(11) 0.0156(11)
    C11 0.0520(13) 0.0588(15) 0.0439(13) 0.0149(11) 0.0109(10) 0.0087(11)
    C12 0.0591(15) 0.0800(19) 0.0465(14) 0.0117(14) 0.0044(11) 0.0053(13)
    C13 0.087(2) 0.0675(19) 0.0558(17) -0.0051(16) 0.0171(15) 0.0045(13)
    C14 0.094(2) 0.0607(17) 0.0593(17) 0.0093(15) 0.0109(15) 0.0299(14)
    C15 0.085(2) 0.0666(17) 0.0584(16) 0.0319(15) 0.0293(14) 0.0329(13)
    C16 0.092(2) 0.0609(17) 0.0481(15) 0.0189(15) 0.0131(13) 0.0205(12)
    C17 0.0722(17) 0.0759(18) 0.0541(15) 0.0292(14) 0.0270(13) 0.0352(13)
    C18 0.073(2) 0.114(3) 0.100(3) 0.014(2) -0.0005(19) 0.054(2)
    C19 0.124(4) 0.145(4) 0.107(4) -0.007(3) -0.042(3) 0.045(3)
    O1A 0.0990(15) 0.1074(17) 0.0575(12) 0.0444(13) 0.0295(11) 0.0493(12)
    O2A 0.217(4) 0.0739(18) 0.162(3) 0.035(2) 0.101(3) 0.061(2)
    O3A 0.1141(19) 0.0871(17) 0.0886(17) 0.0479(15) 0.0326(15) 0.0208(13)
    O4A 0.158(2) 0.0823(16) 0.0574(13) 0.0197(15) 0.0483(15) 0.0295(11)
    O5A 0.137(2) 0.0827(16) 0.0819(16) 0.0374(15) 0.0402(15) 0.0491(13)
    O6A 0.0938(15) 0.0690(14) 0.0653(13) 0.0195(11) 0.0230(11) 0.0112(10)
    O7A 0.143(2) 0.0989(17) 0.0629(14) 0.0416(16) 0.0566(15) 0.0364(12)
    N1A 0.0965(19) 0.0661(16) 0.0625(15) 0.0235(14) 0.0164(14) 0.0250(12)
    N2A 0.0870(16) 0.0625(15) 0.0475(12) 0.0052(12) 0.0192(11) 0.0224(11)
    N3A 0.0624(13) 0.0688(16) 0.0470(12) 0.0137(11) 0.0110(10) 0.0136(11)
    C1A 0.0504(13) 0.0682(16) 0.0464(13) 0.0124(12) 0.0100(10) 0.0250(12)
    C2A 0.0553(14) 0.0580(15) 0.0505(14) 0.0104(11) 0.0113(11) 0.0206(11)
    C3A 0.0556(14) 0.0602(15) 0.0410(12) 0.0048(11) 0.0099(10) 0.0130(11)
    C4A 0.0541(13) 0.0545(14) 0.0415(12) 0.0022(11) 0.0105(10) 0.0180(10)
    C5A 0.0489(12) 0.0482(13) 0.0495(13) 0.0036(10) 0.0071(10) 0.0151(10)
    C6A 0.0468(12) 0.0622(15) 0.0360(11) 0.0056(11) 0.0072(9) 0.0128(10)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    F1 C10 . 1.358(3) ?
    O1 C6 . 1.191(4) ?
    O2 C6 . 1.327(4) ?
    O2 H2 . 0.8200 ?
    O3 C7 . 1.274(3) ?
    N1 C4 . 1.337(3) ?
    N1 C3 . 1.398(3) ?
    N1 C11 . 1.457(3) ?
    N2 C1 . 1.394(3) ?
    N2 C17 . 1.443(4) ?
    N2 C14 . 1.472(4) ?
    N3 C15 . 1.485(4) ?
    N3 C16 . 1.497(4) ?
    N3 C18 . 1.503(4) ?
    N3 H3A . 0.9100 ?
    C1 C2 . 1.390(3) ?
    C1 C10 . 1.423(4) ?
    C2 C3 . 1.399(3) ?
    C2 H2A . 0.9300 ?
    C3 C8 . 1.403(3) ?
    C4 C5 . 1.373(3) ?
    C4 H4A . 0.9300 ?
    C5 C7 . 1.425(4) ?
    C5 C6 . 1.486(3) ?
    C7 C8 . 1.447(3) ?
    C8 C9 . 1.398(4) ?
    C9 C10 . 1.349(4) ?
    C9 H9A . 0.9300 ?
    C11 C13 . 1.479(4) ?
    C11 C12 . 1.485(4) ?
    C11 H11A . 0.9800 ?
    C12 C13 . 1.475(5) ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
    C13 H13A . 0.9700 ?
    C13 H13B . 0.9700 ?
    C14 C15 . 1.493(4) ?
    C14 H14A . 0.9700 ?
    C14 H14B . 0.9700 ?
    C15 H15A . 0.9700 ?
    C15 H15B . 0.9700 ?
    C16 C17 . 1.519(4) ?
    C16 H16A . 0.9700 ?
    C16 H16B . 0.9700 ?
    C17 H17A . 0.9700 ?
    C17 H17B . 0.9700 ?
    C18 C19 . 1.473(6) ?
    C18 H18A . 0.9700 ?
    C18 H18B . 0.9700 ?
    C19 H19A . 0.9600 ?
    C19 H19B . 0.9600 ?
    C19 H19C . 0.9600 ?
    O1A C1A . 1.245(3) ?
    O2A N1A . 1.199(4) ?
    O3A N1A . 1.207(3) ?
    O4A N2A . 1.218(3) ?
    O5A N2A . 1.222(3) ?
    O6A N3A . 1.224(3) ?
    O7A N3A . 1.215(3) ?
    N1A C2A . 1.465(4) ?
    N2A C4A . 1.443(3) ?
    N3A C6A . 1.453(3) ?
    C1A C6A . 1.447(4) ?
    C1A C2A . 1.451(4) ?
    C2A C3A . 1.348(3) ?
    C3A C4A . 1.399(4) ?
    C3A H3AA . 0.9300 ?
    C4A C5A . 1.368(3) ?
    C5A C6A . 1.373(3) ?
    C5A H5AA . 0.9300 ?
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
    C6 O2 H2 . . 109.5 ?
    C4 N1 C3 . . 119.8(2) ?
    C4 N1 C11 . . 119.3(2) ?
    C3 N1 C11 . . 120.48(19) ?
    C1 N2 C17 . . 118.9(2) ?
    C1 N2 C14 . . 120.3(2) ?
    C17 N2 C14 . . 108.4(2) ?
    C15 N3 C16 . . 110.8(2) ?
    C15 N3 C18 . . 110.0(3) ?
    C16 N3 C18 . . 112.6(3) ?
    C15 N3 H3A . . 107.7 ?
    C16 N3 H3A . . 107.7 ?
    C18 N3 H3A . . 107.7 ?
    C2 C1 N2 . . 123.5(2) ?
    C2 C1 C10 . . 115.7(2) ?
    N2 C1 C10 . . 120.7(2) ?
    C1 C2 C3 . . 121.8(2) ?
    C1 C2 H2A . . 119.1 ?
    C3 C2 H2A . . 119.1 ?
    N1 C3 C2 . . 120.5(2) ?
    N1 C3 C8 . . 119.3(2) ?
    C2 C3 C8 . . 120.3(2) ?
    N1 C4 C5 . . 124.0(2) ?
    N1 C4 H4A . . 118.0 ?
    C5 C4 H4A . . 118.0 ?
    C4 C5 C7 . . 119.5(2) ?
    C4 C5 C6 . . 118.4(2) ?
    C7 C5 C6 . . 122.1(2) ?
    O1 C6 O2 . . 121.3(3) ?
    O1 C6 C5 . . 123.5(3) ?
    O2 C6 C5 . . 115.2(3) ?
    O3 C7 C5 . . 122.2(2) ?
    O3 C7 C8 . . 121.2(2) ?
    C5 C7 C8 . . 116.6(2) ?
    C9 C8 C3 . . 118.4(2) ?
    C9 C8 C7 . . 120.8(2) ?
    C3 C8 C7 . . 120.8(2) ?
    C10 C9 C8 . . 120.2(2) ?
    C10 C9 H9A . . 119.9 ?
    C8 C9 H9A . . 119.9 ?
    C9 C10 F1 . . 117.8(2) ?
    C9 C10 C1 . . 123.5(3) ?
    F1 C10 C1 . . 118.6(2) ?
    N1 C11 C13 . . 119.6(2) ?
    N1 C11 C12 . . 121.4(2) ?
    C13 C11 C12 . . 59.7(2) ?
    N1 C11 H11A . . 115.0 ?
    C13 C11 H11A . . 115.0 ?
    C12 C11 H11A . . 115.0 ?
    C13 C12 C11 . . 60.0(2) ?
    C13 C12 H12A . . 117.8 ?
    C11 C12 H12A . . 117.8 ?
    C13 C12 H12B . . 117.8 ?
    C11 C12 H12B . . 117.8 ?
    H12A C12 H12B . . 114.9 ?
    C12 C13 C11 . . 60.36(19) ?
    C12 C13 H13A . . 117.7 ?
    C11 C13 H13A . . 117.7 ?
    C12 C13 H13B . . 117.7 ?
    C11 C13 H13B . . 117.7 ?
    H13A C13 H13B . . 114.9 ?
    N2 C14 C15 . . 111.8(2) ?
    N2 C14 H14A . . 109.3 ?
    C15 C14 H14A . . 109.3 ?
    N2 C14 H14B . . 109.3 ?
    C15 C14 H14B . . 109.3 ?
    H14A C14 H14B . . 107.9 ?
    N3 C15 C14 . . 111.4(2) ?
    N3 C15 H15A . . 109.3 ?
    C14 C15 H15A . . 109.3 ?
    N3 C15 H15B . . 109.3 ?
    C14 C15 H15B . . 109.3 ?
    H15A C15 H15B . . 108.0 ?
    N3 C16 C17 . . 110.3(2) ?
    N3 C16 H16A . . 109.6 ?
    C17 C16 H16A . . 109.6 ?
    N3 C16 H16B . . 109.6 ?
    C17 C16 H16B . . 109.6 ?
    H16A C16 H16B . . 108.1 ?
    N2 C17 C16 . . 112.2(2) ?
    N2 C17 H17A . . 109.2 ?
    C16 C17 H17A . . 109.2 ?
    N2 C17 H17B . . 109.2 ?
    C16 C17 H17B . . 109.2 ?
    H17A C17 H17B . . 107.9 ?
    C19 C18 N3 . . 113.3(3) ?
    C19 C18 H18A . . 108.9 ?
    N3 C18 H18A . . 108.9 ?
    C19 C18 H18B . . 108.9 ?
    N3 C18 H18B . . 108.9 ?
    H18A C18 H18B . . 107.7 ?
    C18 C19 H19A . . 109.5 ?
    C18 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    C18 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 109.5 ?
    O2A N1A O3A . . 123.2(3) ?
    O2A N1A C2A . . 118.8(3) ?
    O3A N1A C2A . . 118.0(3) ?
    O4A N2A O5A . . 123.8(2) ?
    O4A N2A C4A . . 118.1(2) ?
    O5A N2A C4A . . 118.1(2) ?
    O7A N3A O6A . . 121.8(2) ?
    O7A N3A C6A . . 119.9(2) ?
    O6A N3A C6A . . 118.2(2) ?
    O1A C1A C6A . . 126.2(2) ?
    O1A C1A C2A . . 122.3(3) ?
    C6A C1A C2A . . 111.4(2) ?
    C3A C2A C1A . . 124.9(2) ?
    C3A C2A N1A . . 116.8(2) ?
    C1A C2A N1A . . 118.3(2) ?
    C2A C3A C4A . . 119.2(2) ?
    C2A C3A H3AA . . 120.4 ?
    C4A C3A H3AA . . 120.4 ?
    C5A C4A C3A . . 120.4(2) ?
    C5A C4A N2A . . 120.3(2) ?
    C3A C4A N2A . . 119.3(2) ?
    C4A C5A C6A . . 120.1(2) ?
    C4A C5A H5AA . . 120.0 ?
    C6A C5A H5AA . . 120.0 ?
    C5A C6A C1A . . 123.7(2) ?
    C5A C6A N3A . . 116.4(2) ?
    C1A C6A N3A . . 119.9(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
    C17 N2 C1 C2 . . . . 0.3(4) ?
    C14 N2 C1 C2 . . . . -137.6(3) ?
    C17 N2 C1 C10 . . . . -176.1(2) ?
    C14 N2 C1 C10 . . . . 46.0(3) ?
    N2 C1 C2 C3 . . . . 179.7(2) ?
    C10 C1 C2 C3 . . . . -3.8(3) ?
    C4 N1 C3 C2 . . . . 178.3(2) ?
    C11 N1 C3 C2 . . . . -8.4(3) ?
    C4 N1 C3 C8 . . . . -1.5(3) ?
    C11 N1 C3 C8 . . . . 171.75(19) ?
    C1 C2 C3 N1 . . . . -178.5(2) ?
    C1 C2 C3 C8 . . . . 1.3(3) ?
    C3 N1 C4 C5 . . . . -0.1(3) ?
    C11 N1 C4 C5 . . . . -173.4(2) ?
    N1 C4 C5 C7 . . . . 2.5(3) ?
    N1 C4 C5 C6 . . . . -179.3(2) ?
    C4 C5 C6 O1 . . . . 7.0(4) ?
    C7 C5 C6 O1 . . . . -174.8(3) ?
    C4 C5 C6 O2 . . . . -174.1(2) ?
    C7 C5 C6 O2 . . . . 4.1(4) ?
    C4 C5 C7 O3 . . . . 176.0(2) ?
    C6 C5 C7 O3 . . . . -2.2(3) ?
    C4 C5 C7 C8 . . . . -3.0(3) ?
    C6 C5 C7 C8 . . . . 178.8(2) ?
    N1 C3 C8 C9 . . . . -178.78(19) ?
    C2 C3 C8 C9 . . . . 1.4(3) ?
    N1 C3 C8 C7 . . . . 0.7(3) ?
    C2 C3 C8 C7 . . . . -179.07(19) ?
    O3 C7 C8 C9 . . . . 2.0(3) ?
    C5 C7 C8 C9 . . . . -179.0(2) ?
    O3 C7 C8 C3 . . . . -177.5(2) ?
    C5 C7 C8 C3 . . . . 1.5(3) ?
    C3 C8 C9 C10 . . . . -1.4(3) ?
    C7 C8 C9 C10 . . . . 179.1(2) ?
    C8 C9 C10 F1 . . . . 176.6(2) ?
    C8 C9 C10 C1 . . . . -1.4(4) ?
    C2 C1 C10 C9 . . . . 3.9(4) ?
    N2 C1 C10 C9 . . . . -179.4(2) ?
    C2 C1 C10 F1 . . . . -174.0(2) ?
    N2 C1 C10 F1 . . . . 2.6(4) ?
    C4 N1 C11 C13 . . . . -41.8(3) ?
    C3 N1 C11 C13 . . . . 145.0(2) ?
    C4 N1 C11 C12 . . . . -112.3(3) ?
    C3 N1 C11 C12 . . . . 74.5(3) ?
    N1 C11 C12 C13 . . . . 108.3(3) ?
    N1 C11 C13 C12 . . . . -111.2(3) ?
    C1 N2 C14 C15 . . . . 82.1(3) ?
    C17 N2 C14 C15 . . . . -59.7(3) ?
    C16 N3 C15 C14 . . . . -52.8(3) ?
    C18 N3 C15 C14 . . . . -177.9(2) ?
    N2 C14 C15 N3 . . . . 57.1(3) ?
    C15 N3 C16 C17 . . . . 52.0(3) ?
    C18 N3 C16 C17 . . . . 175.7(2) ?
    C1 N2 C17 C16 . . . . -82.7(3) ?
    C14 N2 C17 C16 . . . . 59.7(3) ?
    N3 C16 C17 N2 . . . . -57.0(3) ?
    C15 N3 C18 C19 . . . . -163.2(3) ?
    C16 N3 C18 C19 . . . . 72.6(4) ?
    O1A C1A C2A C3A . . . . 171.7(3) ?
    C6A C1A C2A C3A . . . . -5.5(4) ?
    O1A C1A C2A N1A . . . . -8.2(4) ?
    C6A C1A C2A N1A . . . . 174.5(2) ?
    O2A N1A C2A C3A . . . . 140.3(3) ?
    O3A N1A C2A C3A . . . . -38.2(4) ?
    O2A N1A C2A C1A . . . . -39.8(4) ?
    O3A N1A C2A C1A . . . . 141.7(3) ?
    C1A C2A C3A C4A . . . . 2.8(4) ?
    N1A C2A C3A C4A . . . . -177.3(2) ?
    C2A C3A C4A C5A . . . . 1.4(4) ?
    C2A C3A C4A N2A . . . . 179.8(2) ?
    O4A N2A C4A C5A . . . . -173.7(3) ?
    O5A N2A C4A C5A . . . . 5.2(4) ?
    O4A N2A C4A C3A . . . . 7.9(4) ?
    O5A N2A C4A C3A . . . . -173.2(3) ?
    C3A C4A C5A C6A . . . . -2.1(4) ?
    N2A C4A C5A C6A . . . . 179.5(2) ?
    C4A C5A C6A C1A . . . . -1.3(4) ?
    C4A C5A C6A N3A . . . . -180.0(2) ?
    O1A C1A C6A C5A . . . . -172.4(3) ?
    C2A C1A C6A C5A . . . . 4.7(3) ?
    O1A C1A C6A N3A . . . . 6.3(4) ?
    C2A C1A C6A N3A . . . . -176.6(2) ?
    O7A N3A C6A C5A . . . . -165.8(3) ?
    O6A N3A C6A C5A . . . . 11.8(3) ?
    O7A N3A C6A C1A . . . . 15.4(4) ?
    O6A N3A C6A C1A . . . . -167.0(2) ?
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
    O2 H2 O3 . 0.82 1.78 2.536(3) 151
    N3 H3A O1A . 0.91 1.87 2.724(3) 155
    N3 H3A O7A . 0.91 2.38 3.024(3) 128
    C11 H11A O3 2_565 0.98 2.55 3.385(3) 144
    C15 H15B O1 2_665 0.97 2.35 3.312(3) 169
    C17 H17B O3A 2_566 0.97 2.56 3.458(4) 154
    C3A H3AA O3 1_556 0.93 2.55 3.331(3) 142
    C9 H9A O4A 1_554 0.93 2.58 3.495(3) 170
    C14 H14B O5A 2_556 0.97 2.60 3.517(4) 157
    C18 H18A O5A 2_656 0.97 2.50 3.451(5) 167