#------------------------------------------------------------------------------
#$Date: 2019-07-03 13:24:39 +0300 (Wed, 03 Jul 2019) $
#$Revision: 216710 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/73/1547307.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1547307
loop_
_publ_author_name
'N.N. Golovnev'
'M.S. Molokeev'
'M.K. Lesnikov'
'I.V. Sterkhova'
'V.V. Atuchin'
_publ_section_title
;
 Thiobarbiturate and barbiturate salts of pefloxacin drug: Growth,
 structure, thermal stability and IR-spectra
;
_journal_issue                   0
_journal_name_full               'Journal of Molecular Structure'
_journal_page_first              367
_journal_page_last               372
_journal_paper_doi               10.1016/j.molstruc.2017.08.011
_journal_volume                  1149
_journal_year                    2017
_chemical_formula_moiety       'C17 H21 F N3 O3, C4 H3 N2 O3, 1.281(H2 O)'
_chemical_formula_sum            'C21 H25 F N5 O7.28'
_chemical_formula_weight         482.94
_chemical_name_systematic
;
bis(pefloxacinium 2-thiobarbiturate) hydrate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                101.2430(10)
_cell_angle_beta                 92.5140(10)
_cell_angle_gamma                109.4710(10)
_cell_formula_units_Z            4
_cell_length_a                   10.3252(3)
_cell_length_b                   13.8631(4)
_cell_length_c                   16.9586(3)
_cell_measurement_reflns_used    24769
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.511
_cell_measurement_theta_min      2.107
_cell_volume                     2229.09(10)
_computing_cell_refinement       'APEX2 (Bruker, 2003-2008)'
_computing_data_collection       'APEX2 (Bruker, 2003-2008)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2005)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            24769
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.511
_diffrn_reflns_theta_min         2.107
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2004/1. Bruker AXS Inc., Madison, Wisconsin, USA, 2004
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_description       block
_exptl_crystal_F_000             1013
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.626
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     637
_refine_ls_number_reflns         10127
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0550
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1137P)²+0.3971P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1704
_refine_ls_wR_factor_ref         0.1891
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7257
_reflns_number_total             10127
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            PefH2Hba2_2p5H2O.cif
_cod_data_source_block           p3
_cod_depositor_comments
;

2019-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C42 H50 F2 N10 O14.56'
_cod_original_formula_weight         965.88
_cod_original_formula_moiety
;
2(C17 H21 F N3 O3), 2(C4 H3 N2 O3), H2 O, 1.563(O)
;
_cod_original_formula_units_Z            2
_cod_database_code               1547307
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.57001(12) 1.09089(10) 0.10471(9) 0.0470(3) Uani 1 1 d . . . . .
O2A O 0.45190(15) 0.73730(11) 0.05409(11) 0.0580(4) Uani 1 1 d . . . . .
O3A O 0.11326(11) 0.89840(10) 0.07249(8) 0.0408(3) Uani 1 1 d . . . . .
N1A N 0.34225(13) 0.99187(11) 0.08872(9) 0.0360(3) Uani 1 1 d . . . . .
H1A H 0.3208 1.0476 0.0965 0.043 Uiso 1 1 calc R U . . .
N3A N 0.50788(14) 0.91358(11) 0.08216(9) 0.0383(3) Uani 1 1 d . . . . .
H3A H 0.5935 0.9193 0.0871 0.046 Uiso 1 1 calc R U . . .
C2A C 0.47908(16) 1.00364(13) 0.09268(10) 0.0350(4) Uani 1 1 d . . . . .
C4A C 0.40931(18) 0.81261(14) 0.06396(11) 0.0402(4) Uani 1 1 d . . . . .
C5A C 0.27069(18) 0.80658(14) 0.05965(11) 0.0394(4) Uani 1 1 d . . . . .
H5A H 0.2009 0.7410 0.0476 0.047 Uiso 1 1 calc R U . . .
C6A C 0.23555(16) 0.89549(13) 0.07285(10) 0.0339(3) Uani 1 1 d . . . . .
O1B O -0.18666(12) -0.02820(10) 0.08198(9) 0.0475(3) Uani 1 1 d . . . . .
O2B O -0.09475(16) 0.32184(12) 0.15801(11) 0.0688(5) Uani 1 1 d . . . . .
O3B O 0.26345(12) 0.18280(10) 0.11718(8) 0.0453(3) Uani 1 1 d . . . . .
N1B N 0.03767(13) 0.08009(11) 0.10036(9) 0.0365(3) Uani 1 1 d . . . . .
H1B H 0.0640 0.0268 0.0893 0.044 Uiso 1 1 calc R U . . .
N3B N -0.13710(14) 0.14796(12) 0.11903(9) 0.0388(3) Uani 1 1 d . . . . .
H3B H -0.2237 0.1382 0.1197 0.047 Uiso 1 1 calc R U . . .
C2B C -0.10098(16) 0.06165(14) 0.09880(10) 0.0352(4) Uani 1 1 d . . . . .
C4B C -0.04554(19) 0.25074(15) 0.13880(12) 0.0446(4) Uani 1 1 d . . . . .
C5B C 0.09465(19) 0.26423(14) 0.13752(12) 0.0448(4) Uani 1 1 d . . . . .
H5B H 0.1599 0.3318 0.1496 0.054 Uiso 1 1 calc R U . . .
C6B C 0.13858(16) 0.17915(14) 0.11867(10) 0.0366(4) Uani 1 1 d . . . . .
F1 F 0.01215(14) 0.89545(12) 0.43868(8) 0.0651(4) Uani 1 1 d . . . . .
O1C O 0.4260(2) 0.94188(15) 0.62845(11) 0.0772(5) Uani 1 1 d . . . . .
O2C O 0.6541(2) 0.93212(18) 0.68335(14) 0.0922(7) Uani 1 1 d D . . . .
H2C H 0.589(3) 0.960(3) 0.699(2) 0.111 Uiso 1 1 d D U . . .
O3C O 0.7640(2) 0.8488(2) 0.60421(15) 0.1064(8) Uani 1 1 d . . . . .
N1C N -0.09834(15) 0.77045(12) 0.12975(9) 0.0413(3) Uani 1 1 d . . . . .
H0C H -0.0213 0.8137 0.1059 0.050 Uiso 1 1 calc R U . . .
N2C N 0.04727(16) 0.79662(12) 0.28605(9) 0.0429(4) Uani 1 1 d . . . . .
N3C N 0.4850(2) 0.79808(17) 0.40483(12) 0.0631(5) Uani 1 1 d . . . . .
C1C C 0.0097(2) 0.88244(16) 0.26422(12) 0.0483(4) Uani 1 1 d . . . . .
H1AC H 0.0851 0.9263 0.2407 0.058 Uiso 1 1 calc R U . . .
H1BC H -0.0064 0.9256 0.3124 0.058 Uiso 1 1 calc R U . . .
C2C C -0.1190(2) 0.83742(17) 0.20425(12) 0.0486(5) Uani 1 1 d . . . . .
H2AC H -0.1950 0.7960 0.2289 0.058 Uiso 1 1 calc R U . . .
H2BC H -0.1434 0.8942 0.1902 0.058 Uiso 1 1 calc R U . . .
C3C C -0.0584(2) 0.68510(15) 0.15266(12) 0.0485(4) Uani 1 1 d . . . . .
H3AC H -0.0399 0.6429 0.1048 0.058 Uiso 1 1 calc R U . . .
H3BC H -0.1344 0.6400 0.1749 0.058 Uiso 1 1 calc R U . . .
C4C C 0.0678(2) 0.72902(16) 0.21397(12) 0.0467(4) Uani 1 1 d . . . . .
H4AC H 0.0894 0.6717 0.2293 0.056 Uiso 1 1 calc R U . . .
H4BC H 0.1458 0.7689 0.1899 0.056 Uiso 1 1 calc R U . . .
C5C C 0.2246(2) 0.89958(16) 0.49575(12) 0.0495(5) Uani 1 1 d . . . . .
H05C H 0.2088 0.9333 0.5454 0.059 Uiso 1 1 calc R U . . .
C6C C 0.1307(2) 0.87494(16) 0.42960(12) 0.0467(4) Uani 1 1 d . . . . .
C7C C 0.14927(19) 0.82534(15) 0.35236(12) 0.0427(4) Uani 1 1 d . . . . .
C8C C 0.2681(2) 0.80073(18) 0.34625(13) 0.0497(5) Uani 1 1 d . . . . .
H08C H 0.2835 0.7675 0.2962 0.060 Uiso 1 1 calc R U . . .
C9C C 0.3660(2) 0.82454(16) 0.41360(13) 0.0485(5) Uani 1 1 d . . . . .
C10C C 0.3447(2) 0.87442(15) 0.48946(13) 0.0488(5) Uani 1 1 d . . . . .
C11C C 0.4442(2) 0.89665(16) 0.55990(14) 0.0557(5) Uani 1 1 d . . . . .
C12C C 0.5601(2) 0.86446(18) 0.54554(16) 0.0614(6) Uani 1 1 d . . . . .
C13C C 0.5757(2) 0.8182(2) 0.46931(16) 0.0656(6) Uani 1 1 d . . . . .
H13C H 0.6539 0.7999 0.4622 0.079 Uiso 1 1 calc R U . . .
C14C C 0.6697(3) 0.8798(2) 0.61220(19) 0.0772(8) Uani 1 1 d . . . . .
C15C C 0.5130(3) 0.7499(3) 0.3234(2) 0.0984(11) Uani 1 1 d . . . . .
H14C H 0.5844 0.7203 0.3304 0.118 Uiso 1 1 calc R U . . .
H15C H 0.4297 0.6932 0.2964 0.118 Uiso 1 1 calc R U . . .
C16C C 0.5574(4) 0.8265(3) 0.2719(2) 0.1077(12) Uani 1 1 d . . . . .
H16C H 0.5740 0.7922 0.2205 0.129 Uiso 1 1 calc R U . . .
H17C H 0.4862 0.8550 0.2638 0.129 Uiso 1 1 calc R U . . .
H18C H 0.6408 0.8821 0.2977 0.129 Uiso 1 1 calc R U . . .
C17C C -0.2226(2) 0.72761(18) 0.06827(14) 0.0559(5) Uani 1 1 d . . . . .
H19C H -0.2075 0.6800 0.0234 0.067 Uiso 1 1 calc R U . . .
H20C H -0.2386 0.7842 0.0496 0.067 Uiso 1 1 calc R U . . .
H21C H -0.3017 0.6910 0.0922 0.067 Uiso 1 1 calc R U . . .
F2 F 0.51359(13) 0.39899(11) 0.47993(8) 0.0600(3) Uani 1 1 d . . . . .
O1D O 0.94294(17) 0.45851(12) 0.65770(8) 0.0583(4) Uani 1 1 d . . . . .
O2D O 1.17113(17) 0.45023(13) 0.70914(9) 0.0605(4) Uani 1 1 d D . . . .
H2D H 1.0919(18) 0.465(2) 0.7079(17) 0.073 Uiso 1 1 d D U . . .
O3D O 1.28263(19) 0.37253(16) 0.62642(11) 0.0770(5) Uani 1 1 d . . . . .
N1D N 0.47793(15) 0.36174(12) 0.16830(10) 0.0440(4) Uani 1 1 d . . . . .
H0D H 0.3905 0.3026 0.1520 0.053 Uiso 1 1 calc R U . . .
N2D N 0.55414(18) 0.31945(15) 0.31991(10) 0.0549(5) Uani 1 1 d . . . . .
N3D N 0.99784(15) 0.32523(12) 0.42999(9) 0.0413(3) Uani 1 1 d . . . . .
C1D C 0.4462(2) 0.3648(2) 0.31276(13) 0.0583(6) Uani 1 1 d . . . . .
H1AD H 0.4470 0.4106 0.3641 0.070 Uiso 1 1 calc R U . . .
H1BD H 0.3566 0.3090 0.3004 0.070 Uiso 1 1 calc R U . . .
C2D C 0.4667(2) 0.42620(17) 0.24768(13) 0.0527(5) Uani 1 1 d . . . . .
H2AD H 0.3894 0.4502 0.2416 0.063 Uiso 1 1 calc R U . . .
H2BD H 0.5503 0.4875 0.2636 0.063 Uiso 1 1 calc R U . . .
C3D C 0.59007(19) 0.31804(16) 0.17763(13) 0.0469(4) Uani 1 1 d . . . . .
H3AD H 0.6786 0.3747 0.1931 0.056 Uiso 1 1 calc R U . . .
H3BD H 0.5943 0.2737 0.1267 0.056 Uiso 1 1 calc R U . . .
C4D C 0.5601(2) 0.25482(16) 0.24200(12) 0.0500(5) Uani 1 1 d . . . . .
H4AD H 0.4725 0.1974 0.2254 0.060 Uiso 1 1 calc R U . . .
H4BD H 0.6317 0.2250 0.2478 0.060 Uiso 1 1 calc R U . . .
C5D C 0.7325(2) 0.41103(14) 0.52861(11) 0.0427(4) Uani 1 1 d . . . . .
H05D H 0.7165 0.4405 0.5797 0.051 Uiso 1 1 calc R U . . .
C6D C 0.63575(19) 0.38730(14) 0.46449(12) 0.0424(4) Uani 1 1 d . . . . .
C7D C 0.65477(19) 0.34679(14) 0.38408(11) 0.0394(4) Uani 1 1 d . . . . .
C8D C 0.77918(18) 0.32995(14) 0.37458(11) 0.0382(4) Uani 1 1 d . . . . .
H08D H 0.7977 0.3058 0.3227 0.046 Uiso 1 1 calc R U . . .
C9D C 0.87758(18) 0.34821(13) 0.44057(10) 0.0366(4) Uani 1 1 d . . . . .
C10D C 0.85647(19) 0.39182(13) 0.51893(11) 0.0391(4) Uani 1 1 d . . . . .
C11D C 0.9578(2) 0.41407(14) 0.58746(11) 0.0436(4) Uani 1 1 d . . . . .
C12D C 1.0746(2) 0.38399(15) 0.57138(12) 0.0447(4) Uani 1 1 d . . . . .
C13D C 1.0889(2) 0.34137(15) 0.49421(12) 0.0453(4) Uani 1 1 d . . . . .
H13D H 1.1663 0.3224 0.4856 0.054 Uiso 1 1 calc R U . . .
C14D C 1.1855(2) 0.40009(17) 0.63669(13) 0.0535(5) Uani 1 1 d . . . . .
C15D C 1.0254(2) 0.27772(17) 0.34914(12) 0.0492(5) Uani 1 1 d . . . . .
H14D H 1.1239 0.2911 0.3497 0.059 Uiso 1 1 calc R U . . .
H15D H 0.9986 0.3110 0.3091 0.059 Uiso 1 1 calc R U . . .
C16D C 0.9483(3) 0.16079(19) 0.32475(13) 0.0591(5) Uani 1 1 d . . . . .
H16D H 0.9693 0.1337 0.2723 0.071 Uiso 1 1 calc R U . . .
H17D H 0.9760 0.1273 0.3636 0.071 Uiso 1 1 calc R U . . .
H18D H 0.8506 0.1471 0.3229 0.071 Uiso 1 1 calc R U . . .
C17D C 0.4988(3) 0.42308(19) 0.10377(16) 0.0649(6) Uani 1 1 d . . . . .
H19D H 0.5859 0.4800 0.1171 0.078 Uiso 1 1 calc R U . . .
H20D H 0.4254 0.4505 0.0998 0.078 Uiso 1 1 calc R U . . .
H21D H 0.4986 0.3782 0.0529 0.078 Uiso 1 1 calc R U . . .
O1W O 0.2561(3) 0.5401(2) 0.0484(3) 0.1433(12) Uani 1 1 d D . . . .
H11W H 0.260(5) 0.555(3) 0.1056(7) 0.172 Uiso 1 1 d D U . . .
H12W H 0.315(4) 0.600(2) 0.036(2) 0.172 Uiso 1 1 d D U . . .
O2WA O -0.0163(12) 0.4750(9) 0.0995(9) 0.120(4) Uiso 0.255(3) 1 d . . . . .
O2WB O -0.0238(7) 0.4612(5) 0.0474(5) 0.120(3) Uiso 0.453(8) 1 d . . . . .
O3WA O 0.2417(6) 0.5444(4) 0.2228(3) 0.1039(16) Uiso 0.470(3) 1 d . . . . .
O3WB O 0.1378(7) 0.5043(5) 0.1935(4) 0.104(3) Uiso 0.383(7) 1 d . . . . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2A N1A C6A 123.98(14) . .
C2A N1A H1A 118.0 . .
C6A N1A H1A 118.0 . .
C2A N3A C4A 125.05(14) . .
C2A N3A H3A 117.5 . .
C4A N3A H3A 117.5 . .
O1A C2A N3A 122.57(15) . .
O1A C2A N1A 121.56(15) . .
N3A C2A N1A 115.87(15) . .
O2A C4A N3A 117.63(16) . .
O2A C4A C5A 126.55(17) . .
N3A C4A C5A 115.82(15) . .
C6A C5A C4A 121.56(16) . .
C6A C5A H5A 119.2 . .
C4A C5A H5A 119.2 . .
O3A C6A C5A 126.34(16) . .
O3A C6A N1A 116.02(15) . .
C5A C6A N1A 117.64(14) . .
C2B N1B C6B 124.20(14) . .
C2B N1B H1B 117.9 . .
C6B N1B H1B 117.9 . .
C2B N3B C4B 125.26(14) . .
C2B N3B H3B 117.4 . .
C4B N3B H3B 117.4 . .
O1B C2B N3B 122.66(15) . .
O1B C2B N1B 121.63(15) . .
N3B C2B N1B 115.68(15) . .
O2B C4B N3B 117.63(17) . .
O2B C4B C5B 126.19(19) . .
N3B C4B C5B 116.15(16) . .
C6B C5B C4B 121.45(17) . .
C6B C5B H5B 119.3 . .
C4B C5B H5B 119.3 . .
O3B C6B N1B 116.38(15) . .
O3B C6B C5B 126.38(16) . .
N1B C6B C5B 117.23(15) . .
C14C O2C H2C 132(3) . .
C2C N1C C3C 108.64(14) . .
C2C N1C C17C 112.44(15) . .
C3C N1C C17C 111.47(15) . .
C2C N1C H0C 108.0 . .
C3C N1C H0C 108.0 . .
C17C N1C H0C 108.0 . .
C7C N2C C4C 115.36(15) . .
C7C N2C C1C 116.18(16) . .
C4C N2C C1C 110.47(15) . .
C13C N3C C9C 119.6(2) . .
C13C N3C C15C 119.6(2) . .
C9C N3C C15C 120.75(18) . .
N2C C1C C2C 109.68(16) . .
N2C C1C H1AC 109.7 . .
C2C C1C H1AC 109.7 . .
N2C C1C H1BC 109.7 . .
C2C C1C H1BC 109.7 . .
H1AC C1C H1BC 108.2 . .
N1C C2C C1C 111.28(15) . .
N1C C2C H2AC 109.4 . .
C1C C2C H2AC 109.4 . .
N1C C2C H2BC 109.4 . .
C1C C2C H2BC 109.4 . .
H2AC C2C H2BC 108.0 . .
N1C C3C C4C 111.10(16) . .
N1C C3C H3AC 109.4 . .
C4C C3C H3AC 109.4 . .
N1C C3C H3BC 109.4 . .
C4C C3C H3BC 109.4 . .
H3AC C3C H3BC 108.0 . .
N2C C4C C3C 111.61(16) . .
N2C C4C H4AC 109.3 . .
C3C C4C H4AC 109.3 . .
N2C C4C H4BC 109.3 . .
C3C C4C H4BC 109.3 . .
H4AC C4C H4BC 108.0 . .
C6C C5C C10C 120.36(19) . .
C6C C5C H05C 119.8 . .
C10C C5C H05C 119.8 . .
F1 C6C C5C 118.81(18) . .
F1 C6C C7C 118.45(17) . .
C5C C6C C7C 122.70(18) . .
C8C C7C N2C 121.83(18) . .
C8C C7C C6C 116.84(17) . .
N2C C7C C6C 121.21(17) . .
C7C C8C C9C 121.63(19) . .
C7C C8C H08C 119.2 . .
C9C C8C H08C 119.2 . .
N3C C9C C10C 120.11(18) . .
N3C C9C C8C 119.82(19) . .
C10C C9C C8C 120.07(18) . .
C5C C10C C9C 118.39(18) . .
C5C C10C C11C 121.4(2) . .
C9C C10C C11C 120.2(2) . .
O1C C11C C12C 123.7(2) . .
O1C C11C C10C 120.6(2) . .
C12C C11C C10C 115.7(2) . .
C13C C12C C11C 120.9(2) . .
C13C C12C C14C 117.2(2) . .
C11C C12C C14C 122.0(3) . .
N3C C13C C12C 123.5(2) . .
N3C C13C H13C 118.2 . .
C12C C13C H13C 118.2 . .
O3C C14C O2C 121.4(3) . .
O3C C14C C12C 124.5(3) . .
O2C C14C C12C 114.1(3) . .
C16C C15C N3C 112.4(3) . .
C16C C15C H14C 109.1 . .
N3C C15C H14C 109.1 . .
C16C C15C H15C 109.1 . .
N3C C15C H15C 109.1 . .
H14C C15C H15C 107.8 . .
C15C C16C H16C 109.5 . .
C15C C16C H17C 109.5 . .
H16C C16C H17C 109.5 . .
C15C C16C H18C 109.5 . .
H16C C16C H18C 109.5 . .
H17C C16C H18C 109.5 . .
N1C C17C H19C 109.5 . .
N1C C17C H20C 109.5 . .
H19C C17C H20C 109.5 . .
N1C C17C H21C 109.5 . .
H19C C17C H21C 109.5 . .
H20C C17C H21C 109.5 . .
C14D O2D H2D 111.2(18) . .
C3D N1D C17D 111.76(17) . .
C3D N1D C2D 110.12(14) . .
C17D N1D C2D 111.56(16) . .
C3D N1D H0D 107.7 . .
C17D N1D H0D 107.7 . .
C2D N1D H0D 107.7 . .
C7D N2D C4D 122.11(15) . .
C7D N2D C1D 126.52(16) . .
C4D N2D C1D 110.29(15) . .
C13D N3D C9D 119.96(16) . .
C13D N3D C15D 118.39(16) . .
C9D N3D C15D 121.57(14) . .
N2D C1D C2D 111.57(18) . .
N2D C1D H1AD 109.3 . .
C2D C1D H1AD 109.3 . .
N2D C1D H1BD 109.3 . .
C2D C1D H1BD 109.3 . .
H1AD C1D H1BD 108.0 . .
N1D C2D C1D 111.67(17) . .
N1D C2D H2AD 109.3 . .
C1D C2D H2AD 109.3 . .
N1D C2D H2BD 109.3 . .
C1D C2D H2BD 109.3 . .
H2AD C2D H2BD 107.9 . .
N1D C3D C4D 108.77(16) . .
N1D C3D H3AD 109.9 . .
C4D C3D H3AD 109.9 . .
N1D C3D H3BD 109.9 . .
C4D C3D H3BD 109.9 . .
H3AD C3D H3BD 108.3 . .
N2D C4D C3D 111.46(17) . .
N2D C4D H4AD 109.3 . .
C3D C4D H4AD 109.3 . .
N2D C4D H4BD 109.3 . .
C3D C4D H4BD 109.3 . .
H4AD C4D H4BD 108.0 . .
C6D C5D C10D 120.87(17) . .
C6D C5D H05D 119.6 . .
C10D C5D H05D 119.6 . .
C5D C6D F2 117.26(17) . .
C5D C6D C7D 123.09(17) . .
F2 C6D C7D 119.57(16) . .
N2D C7D C8D 121.47(16) . .
N2D C7D C6D 122.65(17) . .
C8D C7D C6D 115.76(16) . .
C7D C8D C9D 122.20(16) . .
C7D C8D H08D 118.9 . .
C9D C8D H08D 118.9 . .
N3D C9D C8D 121.12(16) . .
N3D C9D C10D 118.88(15) . .
C8D C9D C10D 120.00(16) . .
C5D C10D C9D 117.91(16) . .
C5D C10D C11D 120.99(17) . .
C9D C10D C11D 121.09(17) . .
O1D C11D C12D 122.51(17) . .
O1D C11D C10D 121.46(19) . .
C12D C11D C10D 116.03(17) . .
C13D C12D C11D 120.11(17) . .
C13D C12D C14D 118.12(19) . .
C11D C12D C14D 121.75(19) . .
N3D C13D C12D 123.80(18) . .
N3D C13D H13D 118.1 . .
C12D C13D H13D 118.1 . .
O3D C14D O2D 121.07(19) . .
O3D C14D C12D 124.0(2) . .
O2D C14D C12D 115.0(2) . .
N3D C15D C16D 112.50(16) . .
N3D C15D H14D 109.1 . .
C16D C15D H14D 109.1 . .
N3D C15D H15D 109.1 . .
C16D C15D H15D 109.1 . .
H14D C15D H15D 107.8 . .
C15D C16D H16D 109.5 . .
C15D C16D H17D 109.5 . .
H16D C16D H17D 109.5 . .
C15D C16D H18D 109.5 . .
H16D C16D H18D 109.5 . .
H17D C16D H18D 109.5 . .
N1D C17D H19D 109.5 . .
N1D C17D H20D 109.5 . .
H19D C17D H20D 109.5 . .
N1D C17D H21D 109.5 . .
H19D C17D H21D 109.5 . .
H20D C17D H21D 109.5 . .
H11W O1W H12W 105.8(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1A C2A 1.231(2) .
O2A C4A 1.247(2) .
O3A C6A 1.2764(19) .
N1A C2A 1.364(2) .
N1A C6A 1.387(2) .
N1A H1A 0.8600 .
N3A C2A 1.358(2) .
N3A C4A 1.394(2) .
N3A H3A 0.8600 .
C4A C5A 1.403(2) .
C5A C6A 1.378(2) .
C5A H5A 0.9300 .
O1B C2B 1.233(2) .
O2B C4B 1.249(2) .
O3B C6B 1.275(2) .
N1B C2B 1.366(2) .
N1B C6B 1.385(2) .
N1B H1B 0.8600 .
N3B C2B 1.355(2) .
N3B C4B 1.387(2) .
N3B H3B 0.8600 .
C4B C5B 1.398(3) .
C5B C6B 1.386(3) .
C5B H5B 0.9300 .
F1 C6C 1.355(2) .
O1C C11C 1.263(3) .
O2C C14C 1.327(4) .
O2C H2C 0.906(10) .
O3C C14C 1.191(4) .
N1C C2C 1.484(3) .
N1C C3C 1.487(2) .
N1C C17C 1.489(2) .
N1C H0C 0.9800 .
N2C C7C 1.405(2) .
N2C C4C 1.458(2) .
N2C C1C 1.473(2) .
N3C C13C 1.329(3) .
N3C C9C 1.400(3) .
N3C C15C 1.497(4) .
C1C C2C 1.507(3) .
C1C H1AC 0.9700 .
C1C H1BC 0.9700 .
C2C H2AC 0.9700 .
C2C H2BC 0.9700 .
C3C C4C 1.501(3) .
C3C H3AC 0.9700 .
C3C H3BC 0.9700 .
C4C H4AC 0.9700 .
C4C H4BC 0.9700 .
C5C C6C 1.360(3) .
C5C C10C 1.400(3) .
C5C H05C 0.9300 .
C6C C7C 1.408(3) .
C7C C8C 1.382(3) .
C8C C9C 1.402(3) .
C8C H08C 0.9300 .
C9C C10C 1.400(3) .
C10C C11C 1.454(3) .
C11C C12C 1.424(4) .
C12C C13C 1.368(4) .
C12C C14C 1.496(3) .
C13C H13C 0.9300 .
C15C C16C 1.474(5) .
C15C H14C 0.9700 .
C15C H15C 0.9700 .
C16C H16C 0.9600 .
C16C H17C 0.9600 .
C16C H18C 0.9600 .
C17C H19C 0.9600 .
C17C H20C 0.9600 .
C17C H21C 0.9600 .
F2 C6D 1.354(2) .
O1D C11D 1.271(2) .
O2D C14D 1.329(3) .
O2D H2D 0.910(10) .
O3D C14D 1.195(3) .
N1D C3D 1.491(2) .
N1D C17D 1.493(3) .
N1D C2D 1.496(3) .
N1D H0D 0.9800 .
N2D C7D 1.373(2) .
N2D C4D 1.461(3) .
N2D C1D 1.462(2) .
N3D C13D 1.339(2) .
N3D C9D 1.392(2) .
N3D C15D 1.484(2) .
C1D C2D 1.501(3) .
C1D H1AD 0.9700 .
C1D H1BD 0.9700 .
C2D H2AD 0.9700 .
C2D H2BD 0.9700 .
C3D C4D 1.509(3) .
C3D H3AD 0.9700 .
C3D H3BD 0.9700 .
C4D H4AD 0.9700 .
C4D H4BD 0.9700 .
C5D C6D 1.354(3) .
C5D C10D 1.402(3) .
C5D H05D 0.9300 .
C6D C7D 1.418(3) .
C7D C8D 1.391(2) .
C8D C9D 1.403(2) .
C8D H08D 0.9300 .
C9D C10D 1.407(3) .
C10D C11D 1.442(3) .
C11D C12D 1.422(3) .
C12D C13D 1.363(3) .
C12D C14D 1.486(3) .
C13D H13D 0.9300 .
C15D C16D 1.511(3) .
C15D H14D 0.9700 .
C15D H15D 0.9700 .
C16D H16D 0.9600 .
C16D H17D 0.9600 .
C16D H18D 0.9600 .
C17D H19D 0.9600 .
C17D H20D 0.9600 .
C17D H21D 0.9600 .
O1W H11W 0.948(10) .
O1W H12W 0.919(10) .
O2WA O2WB 0.862(12) .
O3WA O3WB 1.075(7) .
