#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/89/2228973.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_2228973
loop_
_publ_author_name
'Jasinski, Jerry P.'
'Butcher, Ray J.'
'Siddegowda, M. S.'
'Yathirajan, H. S.'
'Siddaraju, B. P.'
_publ_section_title
;
 Enrofloxacinium picrate
;
_journal_coeditor_code           BT5451
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o432
_journal_page_last               o433
_journal_paper_doi               10.1107/S160053681100170X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C19 H23 F N3 O3 +, C6 H2 N3 O7 -'
_chemical_formula_moiety         'C19 H23 F N3 O3 +, C6 H2 N3 O7 -'
_chemical_formula_sum            'C25 H25 F N6 O10'
_chemical_formula_weight         588.51
_chemical_name_common            'Enrofloxacinium picrate'
_chemical_name_systematic
;
4-(3-carboxy-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)-1-ethylpiperazin-1-ium
2,4,6-trinitrophenolate
;
_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
_cell_angle_alpha                105.556(2)
_cell_angle_beta                 96.367(6)
_cell_angle_gamma                96.223(7)
_cell_formula_units_Z            2
_cell_length_a                   7.2111(7)
_cell_length_b                   12.5766(7)
_cell_length_c                   16.2362(4)
_cell_measurement_reflns_used    2958
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      73.4307
_cell_measurement_theta_min      5.2649
_cell_volume                     1395.04(16)
_computing_cell_refinement
'CrysAlis PRO (Oxford Diffraction, 2007)'
_computing_data_collection
'CrysAlis PRO (Oxford Diffraction, 2007)'
_computing_data_reduction
'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.5081
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Ruby Gemini'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0436
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9440
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         73.59
_diffrn_reflns_theta_min         5.27
_exptl_absorpt_coefficient_mu    0.981
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89570
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2007)
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.196
_refine_ls_extinction_coef       0.0007(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         5437
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0553
_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)+(0.0924P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1568
_refine_ls_wR_factor_ref         0.1774
_reflns_number_gt                3425
_reflns_number_total             5437
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5451.cif
_cod_data_source_block           I
_cod_database_code               2228973
_cod_database_fobs_code          2228973
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
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_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'
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_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_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
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) ?
