#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/90/2229046.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_2229046
loop_
_publ_author_name
'Jasinski, Jerry P.'
'Butcher, Ray J.'
'Siddegowda, M. S.'
'Yathirajan, H. S.'
'Hakim Al-arique, Q. N. M.'
_publ_section_title
;
 Lomefloxacinium picrate
;
_journal_coeditor_code           FL2332
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o483
_journal_page_last               o484
_journal_paper_doi               10.1107/S1600536811002534
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C17 H20 F2 N3 O3 +, C6 H2 N3 O7 -'
_chemical_formula_moiety         'C17 H20 F2 N3 O3 +, C6 H2 N3 O7 -'
_chemical_formula_sum            'C23 H22 F2 N6 O10'
_chemical_formula_weight         580.47
_chemical_name_systematic
;
(RS)-4-(3-carboxy-1-ethyl-6,8-difluoro-4-oxo-1,4-dihydroquinolin-7-yl)-
2-methylpiperazin-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                92.969(3)
_cell_angle_beta                 115.555(3)
_cell_angle_gamma                109.852(3)
_cell_formula_units_Z            2
_cell_length_a                   10.9314(4)
_cell_length_b                   11.6748(4)
_cell_length_c                   12.0530(4)
_cell_measurement_reflns_used    6216
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      73.8423
_cell_measurement_theta_min      4.6748
_cell_volume                     1269.14(9)
_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      123(2)
_diffrn_detector_area_resol_mean 10.5081
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_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  0.0175
_diffrn_reflns_av_sigmaI/netI    0.0151
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8890
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         74.00
_diffrn_reflns_theta_min         4.68
_exptl_absorpt_coefficient_mu    1.128
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83782
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2007)
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.588
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         5002
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0677
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0848P)²+0.7775P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1931
_refine_ls_wR_factor_ref         0.1975
_reflns_number_gt                4423
_reflns_number_total             5002
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl2332.cif
_cod_data_source_block           I
_cod_original_cell_volume        1269.14(8)
_cod_database_code               2229046
_cod_database_fobs_code          2229046
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 0.6041(2) 0.51552(14) 0.14890(17) 0.0702(5) Uani d . 1 . .
F F2 0.5633(2) 0.21345(13) 0.38653(13) 0.0626(5) Uani d . 1 . .
O O1 0.1693(3) -0.2597(2) -0.1643(2) 0.0873(8) Uani d . 1 . .
O O2 0.1665(3) -0.1195(2) -0.2795(2) 0.0762(7) Uani d . 1 . .
H H2 0.1948 -0.0413 -0.2670 0.114 Uiso calc R 1 . .
O O3 0.3100(2) 0.1106(2) -0.17445(17) 0.0677(6) Uani d . 1 . .
N N1 0.4330(2) 0.01780(17) 0.16877(19) 0.0436(5) Uani d . 1 . .
N N2 0.6695(3) 0.46292(19) 0.3820(2) 0.0533(6) Uani d . 1 . .
N N3 0.8631(2) 0.67661(19) 0.58301(19) 0.0496(5) Uani d . 1 . .
H H3A 0.9470 0.7498 0.6208 0.060 Uiso calc R 1 . .
H H3B 0.8207 0.6649 0.6352 0.060 Uiso calc R 1 . .
C C1 0.3493(3) -0.0691(2) 0.0590(2) 0.0482(6) Uani d . 1 . .
H H1A 0.3202 -0.1545 0.0631 0.058 Uiso calc R 1 . .
C C2 0.3035(3) -0.0441(2) -0.0569(2) 0.0495(6) Uani d . 1 . .
C C3 0.3465(3) 0.0821(3) -0.0690(2) 0.0485(6) Uani d . 1 . .
C C4 0.4355(2) 0.1778(2) 0.0492(2) 0.0418(5) Uani d . 1 . .
C C5 0.4789(3) 0.3043(2) 0.0451(2) 0.0478(6) Uani d . 1 . .
H H5A 0.4542 0.3271 -0.0338 0.057 Uiso calc R 1 . .
C C6 0.5558(3) 0.3938(2) 0.1536(2) 0.0484(6) Uani d . 1 . .
C C7 0.5904(3) 0.3680(2) 0.2737(2) 0.0435(5) Uani d . 1 . .
C C8 0.5437(3) 0.2414(2) 0.2746(2) 0.0430(5) Uani d . 1 . .
C C9 0.4727(2) 0.1443(2) 0.1660(2) 0.0391(5) Uani d . 1 . .
C C10 0.6250(3) 0.5649(3) 0.3947(3) 0.0626(8) Uani d . 1 . .
H H10A 0.5717 0.5482 0.4448 0.075 Uiso calc R 1 . .
H H10B 0.5562 0.5690 0.3098 0.075 Uiso calc R 1 . .
C C11 0.7563(3) 0.6884(2) 0.4582(3) 0.0592(7) Uani d . 1 . .
H H11A 0.8060 0.7051 0.4044 0.071 Uiso calc R 1 . .
C C12 0.7179(5) 0.7965(3) 0.4768(4) 0.0860(12) Uani d . 1 . .
H H12A 0.8083 0.8737 0.5171 0.129 Uiso calc R 1 . .
H H12B 0.6708 0.7830 0.5309 0.129 Uiso calc R 1 . .
H H12C 0.6495 0.8038 0.3946 0.129 Uiso calc R 1 . .
C C13 0.9051(3) 0.5702(3) 0.5682(3) 0.0572(7) Uani d . 1 . .
H H13A 0.9588 0.5861 0.5184 0.069 Uiso calc R 1 . .
H H13B 0.9723 0.5637 0.6526 0.069 Uiso calc R 1 . .
C C14 0.7718(3) 0.4506(2) 0.5035(3) 0.0604(8) Uani d . 1 . .
H H14A 0.8010 0.3818 0.4899 0.072 Uiso calc R 1 . .
H H14B 0.7229 0.4303 0.5567 0.072 Uiso calc R 1 . .
C C15 0.4738(3) -0.0307(2) 0.2860(3) 0.0547(6) Uani d . 1 . .
H H15A 0.5682 0.0326 0.3549 0.066 Uiso calc R 1 . .
H H15B 0.4897 -0.1073 0.2707 0.066 Uiso calc R 1 . .
C C16 0.3574(4) -0.0604(3) 0.3270(3) 0.0721(9) Uani d . 1 . .
H H16A 0.3826 -0.1023 0.3970 0.108 Uiso calc R 1 . .
H H16B 0.2612 -0.1157 0.2559 0.108 Uiso calc R 1 . .
H H16C 0.3522 0.0173 0.3550 0.108 Uiso calc R 1 . .
C C17 0.2083(3) -0.1516(3) -0.1695(3) 0.0635(8) Uani d . 1 . .
O O1B 0.7431(2) 0.60714(18) 0.73716(18) 0.0620(5) Uani d . 1 A .
O O2B 0.9064(3) 0.8637(2) 0.7905(2) 0.0755(7) Uani d . 1 . .
O O3B 0.8490(2) 0.94720(17) 0.9138(2) 0.0563(5) Uani d . 1 . .
O O4B 1.0085(4) 0.8183(3) 1.3141(2) 0.0968(9) Uani d . 1 . .
O O5B 0.9630(4) 0.6231(3) 1.3095(2) 0.0926(8) Uani d . 1 . .
O O6A 0.6327(5) 0.3366(3) 0.8566(5) 0.1035(10) Uani d PD 0.762(4) A 1
O O7A 0.7909(5) 0.3882(3) 0.7890(4) 0.1035(10) Uani d PD 0.762(4) A 1
O O6B 0.6273(9) 0.3566(9) 0.7639(9) 0.1035(10) Uani d PD 0.238(4) A 2
O O7B 0.8257(10) 0.3560(9) 0.9080(10) 0.1035(10) Uani d PD 0.238(4) A 2
N N1B 0.8724(2) 0.86209(18) 0.8747(2) 0.0466(5) Uani d . 1 . .
N N2B 0.9639(3) 0.7109(3) 1.2577(3) 0.0683(7) Uani d . 1 . .
N N3B 0.7447(3) 0.4116(2) 0.8604(3) 0.0675(7) Uani d D 1 . .
C C1B 0.7998(3) 0.6332(2) 0.8548(2) 0.0476(6) Uani d . 1 . .
C C2B 0.8633(3) 0.7566(2) 0.9345(2) 0.0443(5) Uani d . 1 A .
C C3B 0.9121(3) 0.7818(2) 1.0621(2) 0.0482(6) Uani d . 1 . .
H H3BA 0.9482 0.8649 1.1084 0.058 Uiso calc R 1 A .
C C4B 0.9077(3) 0.6843(3) 1.1220(3) 0.0544(6) Uani d . 1 A .
C C5B 0.8520(3) 0.5620(3) 1.0552(3) 0.0593(7) Uani d . 1 . .
H H5BA 0.8492 0.4953 1.0972 0.071 Uiso calc R 1 A .
C C6B 0.8019(3) 0.5399(2) 0.9289(3) 0.0544(6) Uani d . 1 A .
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
C17 O2 H2 . . 109.5 ?
C1 N1 C9 . . 119.0(2) ?
C1 N1 C15 . . 116.0(2) ?
C9 N1 C15 . . 125.02(19) ?
C7 N2 C10 . . 121.8(2) ?
C7 N2 C14 . . 122.7(2) ?
C10 N2 C14 . . 112.8(2) ?
C13 N3 C11 . . 112.07(19) ?
C13 N3 H3A . . 109.2 ?
C11 N3 H3A . . 109.2 ?
C13 N3 H3B . . 109.2 ?
C11 N3 H3B . . 109.2 ?
H3A N3 H3B . . 107.9 ?
N1 C1 C2 . . 124.9(2) ?
N1 C1 H1A . . 117.5 ?
C2 C1 H1A . . 117.5 ?
C1 C2 C3 . . 120.0(2) ?
C1 C2 C17 . . 118.2(3) ?
C3 C2 C17 . . 121.8(3) ?
O3 C3 C2 . . 122.7(2) ?
O3 C3 C4 . . 121.5(3) ?
C2 C3 C4 . . 115.8(2) ?
C5 C4 C9 . . 120.0(2) ?
C5 C4 C3 . . 119.2(2) ?
C9 C4 C3 . . 120.7(2) ?
C6 C5 C4 . . 119.9(2) ?
C6 C5 H5A . . 120.1 ?
C4 C5 H5A . . 120.1 ?
C5 C6 F1 . . 119.3(2) ?
C5 C6 C7 . . 123.6(2) ?
F1 C6 C7 . . 117.2(2) ?
N2 C7 C8 . . 123.3(2) ?
N2 C7 C6 . . 121.4(2) ?
C8 C7 C6 . . 115.2(2) ?
F2 C8 C7 . . 116.6(2) ?
F2 C8 C9 . . 119.6(2) ?
C7 C8 C9 . . 123.8(2) ?
N1 C9 C4 . . 119.3(2) ?
N1 C9 C8 . . 123.4(2) ?
C4 C9 C8 . . 117.2(2) ?
N2 C10 C11 . . 111.5(2) ?
N2 C10 H10A . . 109.3 ?
C11 C10 H10A . . 109.3 ?
N2 C10 H10B . . 109.3 ?
C11 C10 H10B . . 109.3 ?
H10A C10 H10B . . 108.0 ?
C12 C11 C10 . . 114.0(3) ?
C12 C11 N3 . . 110.5(2) ?
C10 C11 N3 . . 108.1(2) ?
C12 C11 H11A . . 108.0 ?
C10 C11 H11A . . 108.0 ?
N3 C11 H11A . . 108.0 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C14 C13 N3 . . 110.8(2) ?
C14 C13 H13A . . 109.5 ?
N3 C13 H13A . . 109.5 ?
C14 C13 H13B . . 109.5 ?
N3 C13 H13B . . 109.5 ?
H13A C13 H13B . . 108.1 ?
N2 C14 C13 . . 109.3(2) ?
N2 C14 H14A . . 109.8 ?
C13 C14 H14A . . 109.8 ?
N2 C14 H14B . . 109.8 ?
C13 C14 H14B . . 109.8 ?
H14A C14 H14B . . 108.3 ?
N1 C15 C16 . . 112.5(2) ?
N1 C15 H15A . . 109.1 ?
C16 C15 H15A . . 109.1 ?
N1 C15 H15B . . 109.1 ?
C16 C15 H15B . . 109.1 ?
H15A C15 H15B . . 107.8 ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
O1 C17 O2 . . 121.1(3) ?
O1 C17 C2 . . 124.3(3) ?
O2 C17 C2 . . 114.5(3) ?
O2B N1B O3B . . 122.9(2) ?
O2B N1B C2B . . 118.9(2) ?
O3B N1B C2B . . 118.1(2) ?
O4B N2B O5B . . 123.5(3) ?
O4B N2B C4B . . 118.7(3) ?
O5B N2B C4B . . 117.9(3) ?
O6A N3B O7A . . 121.6(3) ?
O6B N3B O7B . . 119.2(6) ?
O6B N3B C6B . . 126.3(5) ?
O6A N3B C6B . . 117.5(3) ?
O7A N3B C6B . . 119.2(3) ?
O7B N3B C6B . . 114.5(5) ?
O1B C1B C2B . . 125.8(2) ?
O1B C1B C6B . . 123.3(2) ?
C2B C1B C6B . . 110.8(2) ?
C3B C2B C1B . . 124.9(2) ?
C3B C2B N1B . . 117.3(2) ?
C1B C2B N1B . . 117.8(2) ?
C2B C3B C4B . . 118.7(2) ?
C2B C3B H3BA . . 120.7 ?
C4B C3B H3BA . . 120.7 ?
C3B C4B C5B . . 121.3(3) ?
C3B C4B N2B . . 119.0(3) ?
C5B C4B N2B . . 119.7(3) ?
C6B C5B C4B . . 118.5(3) ?
C6B C5B H5BA . . 120.7 ?
C4B C5B H5BA . . 120.7 ?
C5B C6B C1B . . 125.7(3) ?
C5B C6B N3B . . 117.9(3) ?
C1B C6B N3B . . 116.4(3) ?
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 C6 . 1.351(3) ?
F2 C8 . 1.348(3) ?
O1 C17 . 1.202(4) ?
O2 C17 . 1.323(4) ?
O2 H2 . 0.8400 ?
O3 C3 . 1.258(3) ?
N1 C1 . 1.343(3) ?
N1 C9 . 1.397(3) ?
N1 C15 . 1.492(3) ?
N2 C7 . 1.381(3) ?
N2 C10 . 1.455(3) ?
N2 C14 . 1.460(3) ?
N3 C13 . 1.490(3) ?
N3 C11 . 1.504(3) ?
N3 H3A . 0.9200 ?
N3 H3B . 0.9200 ?
C1 C2 . 1.351(4) ?
C1 H1A . 0.9500 ?
C2 C3 . 1.422(4) ?
C2 C17 . 1.489(3) ?
C3 C4 . 1.459(3) ?
C4 C5 . 1.400(4) ?
C4 C9 . 1.405(3) ?
C5 C6 . 1.350(4) ?
C5 H5A . 0.9500 ?
C6 C7 . 1.407(4) ?
C7 C8 . 1.392(3) ?
C8 C9 . 1.405(3) ?
C10 C11 . 1.503(4) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 C12 . 1.493(4) ?
C11 H11A . 1.0000 ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 0.9800 ?
C13 C14 . 1.485(4) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 C16 . 1.499(5) ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 0.9800 ?
O1B C1B . 1.248(3) ?
O2B N1B . 1.221(3) ?
O3B N1B . 1.226(3) ?
O4B N2B . 1.218(4) ?
O5B N2B . 1.227(4) ?
O6A N3B . 1.219(3) ?
O7A N3B . 1.2298(19) ?
O6B N3B . 1.219(5) ?
O7B N3B . 1.234(2) ?
N1B C2B . 1.455(3) ?
N2B C4B . 1.449(4) ?
N3B C6B . 1.451(3) ?
C1B C2B . 1.443(3) ?
C1B C6B . 1.444(4) ?
C2B C3B . 1.370(4) ?
C3B C4B . 1.377(4) ?
C3B H3BA . 0.9500 ?
C4B C5B . 1.388(4) ?
C5B C6B . 1.351(4) ?
C5B H5BA . 0.9500 ?
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 . 0.84 1.74 2.520(3) 153
N3 H3A O2 1_666 0.92 2.09 2.984(3) 164
N3 H3B O1B . 0.92 1.81 2.714(3) 166
N3 H3B O2B . 0.92 2.52 2.993(3) 113
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
C9 N1 C1 C2 . . . . 2.6(4) ?
C15 N1 C1 C2 . . . . -178.6(2) ?
N1 C1 C2 C3 . . . . 1.4(4) ?
N1 C1 C2 C17 . . . . -178.7(2) ?
C1 C2 C3 O3 . . . . 178.3(2) ?
C17 C2 C3 O3 . . . . -1.6(4) ?
C1 C2 C3 C4 . . . . -2.2(4) ?
C17 C2 C3 C4 . . . . 177.9(2) ?
O3 C3 C4 C5 . . . . 1.2(4) ?
C2 C3 C4 C5 . . . . -178.3(2) ?
O3 C3 C4 C9 . . . . 178.6(2) ?
C2 C3 C4 C9 . . . . -0.9(3) ?
C9 C4 C5 C6 . . . . -0.3(4) ?
C3 C4 C5 C6 . . . . 177.1(2) ?
C4 C5 C6 F1 . . . . 176.3(2) ?
C4 C5 C6 C7 . . . . -3.2(4) ?
C10 N2 C7 C8 . . . . -129.4(3) ?
C14 N2 C7 C8 . . . . 30.8(4) ?
C10 N2 C7 C6 . . . . 52.8(4) ?
C14 N2 C7 C6 . . . . -146.9(3) ?
C5 C6 C7 N2 . . . . 180.0(2) ?
F1 C6 C7 N2 . . . . 0.4(4) ?
C5 C6 C7 C8 . . . . 2.0(4) ?
F1 C6 C7 C8 . . . . -177.5(2) ?
N2 C7 C8 F2 . . . . 8.0(4) ?
C6 C7 C8 F2 . . . . -174.1(2) ?
N2 C7 C8 C9 . . . . -175.2(2) ?
C6 C7 C8 C9 . . . . 2.7(4) ?
C1 N1 C9 C4 . . . . -5.6(3) ?
C15 N1 C9 C4 . . . . 175.7(2) ?
C1 N1 C9 C8 . . . . 171.8(2) ?
C15 N1 C9 C8 . . . . -6.9(4) ?
C5 C4 C9 N1 . . . . -177.8(2) ?
C3 C4 C9 N1 . . . . 4.8(3) ?
C5 C4 C9 C8 . . . . 4.6(3) ?
C3 C4 C9 C8 . . . . -172.8(2) ?
F2 C8 C9 N1 . . . . -6.6(4) ?
C7 C8 C9 N1 . . . . 176.6(2) ?
F2 C8 C9 C4 . . . . 170.8(2) ?
C7 C8 C9 C4 . . . . -5.9(4) ?
C7 N2 C10 C11 . . . . -139.1(3) ?
C14 N2 C10 C11 . . . . 58.8(4) ?
N2 C10 C11 C12 . . . . -178.6(3) ?
N2 C10 C11 N3 . . . . -55.3(3) ?
C13 N3 C11 C12 . . . . -179.5(3) ?
C13 N3 C11 C10 . . . . 55.1(3) ?
C11 N3 C13 C14 . . . . -57.0(3) ?
C7 N2 C14 C13 . . . . 140.2(3) ?
C10 N2 C14 C13 . . . . -57.9(4) ?
N3 C13 C14 N2 . . . . 56.2(3) ?
C1 N1 C15 C16 . . . . -85.8(3) ?
C9 N1 C15 C16 . . . . 92.9(3) ?
C1 C2 C17 O1 . . . . -0.1(4) ?
C3 C2 C17 O1 . . . . 179.8(3) ?
C1 C2 C17 O2 . . . . 179.2(3) ?
C3 C2 C17 O2 . . . . -0.9(4) ?
O1B C1B C2B C3B . . . . 173.3(3) ?
C6B C1B C2B C3B . . . . -3.2(4) ?
O1B C1B C2B N1B . . . . -4.6(4) ?
C6B C1B C2B N1B . . . . 178.8(2) ?
O2B N1B C2B C3B . . . . 142.1(3) ?
O3B N1B C2B C3B . . . . -36.0(3) ?
O2B N1B C2B C1B . . . . -39.8(3) ?
O3B N1B C2B C1B . . . . 142.1(2) ?
C1B C2B C3B C4B . . . . 3.3(4) ?
N1B C2B C3B C4B . . . . -178.8(2) ?
C2B C3B C4B C5B . . . . -1.6(4) ?
C2B C3B C4B N2B . . . . 177.8(2) ?
O4B N2B C4B C3B . . . . 2.6(4) ?
O5B N2B C4B C3B . . . . -177.9(3) ?
O4B N2B C4B C5B . . . . -178.0(3) ?
O5B N2B C4B C5B . . . . 1.6(4) ?
C3B C4B C5B C6B . . . . 0.2(4) ?
N2B C4B C5B C6B . . . . -179.2(3) ?
C4B C5B C6B C1B . . . . -0.4(5) ?
C4B C5B C6B N3B . . . . 179.7(3) ?
O1B C1B C6B C5B . . . . -174.9(3) ?
C2B C1B C6B C5B . . . . 1.8(4) ?
O1B C1B C6B N3B . . . . 5.0(4) ?
C2B C1B C6B N3B . . . . -178.3(2) ?
O6B N3B C6B C5B . . . . 130.8(9) ?
O6A N3B C6B C5B . . . . 65.1(5) ?
O7A N3B C6B C5B . . . . -129.3(4) ?
O7B N3B C6B C5B . . . . -48.8(7) ?
O6B N3B C6B C1B . . . . -49.1(9) ?
O6A N3B C6B C1B . . . . -114.8(4) ?
O7A N3B C6B C1B . . . . 50.8(5) ?
O7B N3B C6B C1B . . . . 131.3(7) ?
