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#$Date: 2023-12-01 17:04:59 +0200 (Fri, 01 Dec 2023) $
#$Revision: 287935 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/72/8107201.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_8107201
loop_
_publ_author_name
'Jiang, Cheng-Jun'
'Xia, Ying-Fan'
_publ_section_title
;
 The crystal structure of
 bis(4-(6-carboxy-8-ethyl-3-fluoro-5-oxo-5,8-dihydro-1,8-naphthyridin-2-
 yl)piperazin-1-ium) adipate tetrahydrate, C36H52F2N8O14
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              729
_journal_page_last               731
_journal_paper_doi               10.1515/ncrs-2022-0162
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         '2(C15 H18 F N4 O3), 4(H2 O), C6 H8 O4'
_chemical_formula_sum            'C36 H52 F2 N8 O14'
_chemical_formula_weight         858.85
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                103.688(2)
_cell_angle_beta                 92.778(2)
_cell_angle_gamma                106.206(2)
_cell_formula_units_Z            1
_cell_length_a                   6.9775(4)
_cell_length_b                   9.0785(6)
_cell_length_c                   16.8942(10)
_cell_measurement_reflns_used    5213
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.05
_cell_measurement_theta_min      2.42
_cell_volume                     990.91(11)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16926
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.148
_diffrn_reflns_theta_min         2.417
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7157
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1278 before and 0.0812 after correction.
The Ratio of minimum to maximum transmission is 0.9600.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_description       needle
_exptl_crystal_F_000             454
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4372
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0533P)²+0.3002P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1088
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3462
_reflns_number_total             4372
_reflns_threshold_expression     'I > 2φ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0162_suppl.cif
_cod_data_source_block           mo
_cod_database_code               8107201
_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.
;
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.963
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 O6-H6A
 0.87 with sigma of 0.02
3.a Free rotating group:
 O6(H6B), O7(H7A,H7B)
3.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C1(H1C,H1D), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C13(H13A,
 H13B), C17(H17A,H17B), C18(H18A,H18B)
3.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10)
3.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
3.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
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
F1 F 0.54391(18) 0.08485(10) 0.08471(6) 0.0433(3) Uani 1 1 d . . . . .
O1 O 0.78452(16) 0.38446(12) -0.12696(6) 0.0286(2) Uani 1 1 d . . . . .
O2 O 0.9589(2) 0.86045(14) -0.11739(8) 0.0439(3) Uani 1 1 d . . . . .
O3 O 0.91400(18) 0.61436(14) -0.19045(7) 0.0349(3) Uani 1 1 d . . . . .
H3 H 0.869493 0.522204 -0.184385 0.052 Uiso 1 1 calc GR . . . .
N1 N 0.76033(17) 0.35227(14) 0.37883(7) 0.0213(3) Uani 1 1 d . . . . .
H1A H 0.665036 0.333659 0.413165 0.026 Uiso 1 1 calc R . . . .
H1B H 0.882142 0.369992 0.407378 0.026 Uiso 1 1 calc R . . . .
N2 N 0.54156(19) 0.33030(14) 0.22750(7) 0.0238(3) Uani 1 1 d . . . . .
N3 N 0.66426(17) 0.51109(13) 0.15404(7) 0.0199(2) Uani 1 1 d . . . . .
N4 N 0.77448(17) 0.70845(13) 0.08743(7) 0.0209(3) Uani 1 1 d . . . . .
C1 C 0.5295(2) 0.18633(17) 0.25458(9) 0.0261(3) Uani 1 1 d . . . . .
H1C H 0.509316 0.094903 0.206168 0.031 Uiso 1 1 calc R . . . .
H1D H 0.413130 0.163290 0.285818 0.031 Uiso 1 1 calc R . . . .
C2 C 0.7214(2) 0.20890(17) 0.30832(9) 0.0244(3) Uani 1 1 d . . . . .
H2A H 0.709065 0.113885 0.329137 0.029 Uiso 1 1 calc R . . . .
H2B H 0.835791 0.221342 0.275473 0.029 Uiso 1 1 calc R . . . .
C3 C 0.7582(2) 0.49702(17) 0.35203(9) 0.0244(3) Uani 1 1 d . . . . .
H3A H 0.872950 0.526568 0.320767 0.029 Uiso 1 1 calc R . . . .
H3B H 0.772422 0.586740 0.400732 0.029 Uiso 1 1 calc R . . . .
C4 C 0.5625(2) 0.46521(18) 0.29861(9) 0.0254(3) Uani 1 1 d . . . . .
H4A H 0.447922 0.440893 0.330597 0.030 Uiso 1 1 calc R . . . .
H4B H 0.562315 0.560574 0.279870 0.030 Uiso 1 1 calc R . . . .
C5 C 0.6047(2) 0.35929(16) 0.15643(8) 0.0202(3) Uani 1 1 d . . . . .
C6 C 0.6043(2) 0.23981(16) 0.08407(9) 0.0244(3) Uani 1 1 d . . . . .
C7 C 0.6601(2) 0.27632(17) 0.01412(9) 0.0234(3) Uani 1 1 d . . . . .
H7 H 0.659342 0.194720 -0.033083 0.028 Uiso 1 1 calc R . . . .
C8 C 0.7197(2) 0.43658(16) 0.01162(8) 0.0202(3) Uani 1 1 d . . . . .
C9 C 0.7176(2) 0.54752(16) 0.08445(8) 0.0193(3) Uani 1 1 d . . . . .
C10 C 0.8334(2) 0.75503(17) 0.02061(9) 0.0233(3) Uani 1 1 d . . . . .
H10 H 0.874117 0.865640 0.024276 0.028 Uiso 1 1 calc R . . . .
C11 C 0.8383(2) 0.65234(17) -0.05282(9) 0.0229(3) Uani 1 1 d . . . . .
C12 C 0.7808(2) 0.48434(17) -0.06104(9) 0.0215(3) Uani 1 1 d . . . . .
C13 C 0.7742(2) 0.82801(17) 0.16431(9) 0.0250(3) Uani 1 1 d . . . . .
H13A H 0.653363 0.787528 0.190421 0.030 Uiso 1 1 calc R . . . .
H13B H 0.766842 0.926942 0.150991 0.030 Uiso 1 1 calc R . . . .
C14 C 0.9600(3) 0.86489(19) 0.22403(10) 0.0333(4) Uani 1 1 d . . . . .
H14A H 1.079962 0.904474 0.198286 0.050 Uiso 1 1 calc GR . . . .
H14B H 0.964654 0.768135 0.239229 0.050 Uiso 1 1 calc GR . . . .
H14C H 0.955917 0.945997 0.273334 0.050 Uiso 1 1 calc GR . . . .
H6A H 0.613(3) 0.199(2) 0.6641(11) 0.050 Uiso 1 1 d DR . . . .
C15 C 0.9083(2) 0.71961(19) -0.12192(10) 0.0293(3) Uani 1 1 d . . . . .
O4 O 0.43462(15) 0.27607(12) 0.45897(6) 0.0269(2) Uani 1 1 d . . . . .
O5 O 0.62103(16) 0.27011(13) 0.56760(7) 0.0312(3) Uani 1 1 d . . . . .
C16 C 0.4586(2) 0.22506(16) 0.52098(9) 0.0209(3) Uani 1 1 d . . . . .
C17 C 0.2825(2) 0.10104(17) 0.54002(9) 0.0241(3) Uani 1 1 d . . . . .
H17A H 0.318657 0.001184 0.533308 0.029 Uiso 1 1 calc R . . . .
H17B H 0.264444 0.137634 0.598421 0.029 Uiso 1 1 calc R . . . .
C18 C 0.0825(2) 0.06374(17) 0.48852(9) 0.0263(3) Uani 1 1 d . . . . .
H18A H 0.098142 0.027198 0.429838 0.032 Uiso 1 1 calc R . . . .
H18B H 0.041942 0.161861 0.496040 0.032 Uiso 1 1 calc R . . . .
O6 O 0.5790(2) 0.15812(16) 0.70852(8) 0.0443(3) Uani 1 1 d D . . . .
H6B H 0.664408 0.219882 0.750489 0.066 Uiso 1 1 d G . . . .
O7 O 1.15544(15) 0.43331(13) 0.43775(7) 0.0312(3) Uani 1 1 d . . . . .
H7A H 1.238263 0.378885 0.442282 0.047 Uiso 1 1 d G . . . .
H7B H 1.222447 0.527083 0.433637 0.047 Uiso 1 1 d G . . . .
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'
F F 0.0171 0.0103 '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'
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
C15 O3 H3 109.5 . .
H1A N1 H1B 107.8 . .
C2 N1 H1A 109.1 . .
C2 N1 H1B 109.1 . .
C3 N1 H1A 109.1 . .
C3 N1 H1B 109.1 . .
C3 N1 C2 112.43(11) . .
C1 N2 C4 110.15(11) . .
C5 N2 C1 126.32(12) . .
C5 N2 C4 118.87(12) . .
C5 N3 C9 119.82(12) . .
C9 N4 C13 120.41(11) . .
C10 N4 C9 119.42(12) . .
C10 N4 C13 120.15(12) . .
N2 C1 H1C 109.7 . .
N2 C1 H1D 109.7 . .
N2 C1 C2 110.00(11) . .
H1C C1 H1D 108.2 . .
C2 C1 H1C 109.7 . .
C2 C1 H1D 109.7 . .
N1 C2 C1 110.26(12) . .
N1 C2 H2A 109.6 . .
N1 C2 H2B 109.6 . .
C1 C2 H2A 109.6 . .
C1 C2 H2B 109.6 . .
H2A C2 H2B 108.1 . .
N1 C3 H3A 109.7 . .
N1 C3 H3B 109.7 . .
N1 C3 C4 109.86(11) . .
H3A C3 H3B 108.2 . .
C4 C3 H3A 109.7 . .
C4 C3 H3B 109.7 . .
N2 C4 C3 109.15(12) . .
N2 C4 H4A 109.9 . .
N2 C4 H4B 109.9 . .
C3 C4 H4A 109.9 . .
C3 C4 H4B 109.9 . .
H4A C4 H4B 108.3 . .
N2 C5 C6 124.87(13) . .
N3 C5 N2 116.70(12) . .
N3 C5 C6 118.38(12) . .
F1 C6 C5 119.61(13) . .
C7 C6 F1 118.48(13) . .
C7 C6 C5 121.91(13) . .
C6 C7 H7 120.3 . .
C6 C7 C8 119.41(13) . .
C8 C7 H7 120.3 . .
C7 C8 C12 122.45(13) . .
C9 C8 C7 115.84(12) . .
C9 C8 C12 121.71(13) . .
N3 C9 N4 115.74(12) . .
N3 C9 C8 124.62(12) . .
N4 C9 C8 119.64(12) . .
N4 C10 H10 118.1 . .
N4 C10 C11 123.86(13) . .
C11 C10 H10 118.1 . .
C10 C11 C12 120.12(13) . .
C10 C11 C15 118.44(13) . .
C12 C11 C15 121.42(13) . .
O1 C12 C8 121.96(13) . .
O1 C12 C11 122.80(13) . .
C11 C12 C8 115.24(12) . .
N4 C13 H13A 109.2 . .
N4 C13 H13B 109.2 . .
N4 C13 C14 111.88(12) . .
H13A C13 H13B 107.9 . .
C14 C13 H13A 109.2 . .
C14 C13 H13B 109.2 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14B 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
O2 C15 O3 121.12(14) . .
O2 C15 C11 123.46(15) . .
O3 C15 C11 115.42(13) . .
O4 C16 C17 118.59(12) . .
O5 C16 O4 123.46(13) . .
O5 C16 C17 117.95(13) . .
C16 C17 H17A 108.2 . .
C16 C17 H17B 108.2 . .
H17A C17 H17B 107.3 . .
C18 C17 C16 116.38(12) . .
C18 C17 H17A 108.2 . .
C18 C17 H17B 108.2 . .
C17 C18 C18 112.15(16) . 2_556
C17 C18 H18A 109.2 . .
C17 C18 H18B 109.2 . .
C18 C18 H18A 109.2 2_556 .
C18 C18 H18B 109.2 2_556 .
H18A C18 H18B 107.9 . .
H6A O6 H6B 106.8 . .
H7A O7 H7B 109.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C6 1.3541(16) .
O1 C12 1.2654(17) .
O2 C15 1.210(2) .
O3 H3 0.8400 .
O3 C15 1.3257(19) .
N1 H1A 0.9100 .
N1 H1B 0.9100 .
N1 C2 1.4915(18) .
N1 C3 1.4912(18) .
N2 C1 1.4662(18) .
N2 C4 1.4667(18) .
N2 C5 1.3568(18) .
N3 C5 1.3348(18) .
N3 C9 1.3370(18) .
N4 C9 1.3908(17) .
N4 C10 1.3402(18) .
N4 C13 1.4830(18) .
C1 H1C 0.9900 .
C1 H1D 0.9900 .
C1 C2 1.517(2) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C3 C4 1.516(2) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.429(2) .
C6 C7 1.348(2) .
C7 H7 0.9500 .
C7 C8 1.409(2) .
C8 C9 1.3972(19) .
C8 C12 1.4408(19) .
C10 H10 0.9500 .
C10 C11 1.373(2) .
C11 C12 1.435(2) .
C11 C15 1.483(2) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C13 C14 1.511(2) .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
O4 C16 1.2633(17) .
O5 C16 1.2547(18) .
C16 C17 1.5227(18) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C17 C18 1.516(2) .
C18 C18 1.525(3) 2_556
C18 H18A 0.9900 .
C18 H18B 0.9900 .
O6 H6A 0.924(15) .
O6 H6B 0.8700 .
O7 H7A 0.8700 .
O7 H7B 0.8701 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3 O1 0.84 1.75 2.5346(16) 154.0 . yes
N1 H1A O4 0.91 1.82 2.7093(15) 166.3 . yes
N1 H1B O7 0.91 1.84 2.7180(16) 161.5 . yes
C1 H1C F1 0.99 2.06 2.8148(17) 131.3 . yes
O6 H6A O5 0.924(15) 1.890(16) 2.7989(17) 167(2) . yes
O7 H7A O4 0.87 1.90 2.7726(15) 174.9 1_655 yes
O7 H7B O5 0.87 1.87 2.7340(15) 175.5 2_766 yes
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
F1 C6 C7 C8 178.75(13) . . . .
N1 C3 C4 N2 -58.33(15) . . . .
N2 C1 C2 N1 55.86(15) . . . .
N2 C5 C6 F1 -2.3(2) . . . .
N2 C5 C6 C7 176.78(14) . . . .
N3 C5 C6 F1 -179.78(13) . . . .
N3 C5 C6 C7 -0.7(2) . . . .
N4 C10 C11 C12 -0.8(2) . . . .
N4 C10 C11 C15 -179.53(13) . . . .
C1 N2 C4 C3 62.92(15) . . . .
C1 N2 C5 N3 -159.64(13) . . . .
C1 N2 C5 C6 22.9(2) . . . .
C2 N1 C3 C4 54.31(15) . . . .
C3 N1 C2 C1 -52.97(15) . . . .
C4 N2 C1 C2 -61.80(15) . . . .
C4 N2 C5 N3 -6.34(19) . . . .
C4 N2 C5 C6 176.16(13) . . . .
C5 N2 C1 C2 93.43(16) . . . .
C5 N2 C4 C3 -94.40(15) . . . .
C5 N3 C9 N4 179.02(12) . . . .
C5 N3 C9 C8 -1.2(2) . . . .
C5 C6 C7 C8 -0.4(2) . . . .
C6 C7 C8 C9 0.6(2) . . . .
C6 C7 C8 C12 -179.87(14) . . . .
C7 C8 C9 N3 0.1(2) . . . .
C7 C8 C9 N4 179.91(12) . . . .
C7 C8 C12 O1 0.0(2) . . . .
C7 C8 C12 C11 -179.52(13) . . . .
C9 N3 C5 N2 -176.27(12) . . . .
C9 N3 C5 C6 1.40(19) . . . .
C9 N4 C10 C11 1.2(2) . . . .
C9 N4 C13 C14 80.31(16) . . . .
C9 C8 C12 O1 179.42(13) . . . .
C9 C8 C12 C11 -0.07(19) . . . .
C10 N4 C9 N3 178.87(12) . . . .
C10 N4 C9 C8 -0.97(19) . . . .
C10 N4 C13 C14 -98.41(16) . . . .
C10 C11 C12 O1 -179.24(13) . . . .
C10 C11 C12 C8 0.2(2) . . . .
C10 C11 C15 O2 -1.0(2) . . . .
C10 C11 C15 O3 178.45(13) . . . .
C12 C8 C9 N3 -179.39(13) . . . .
C12 C8 C9 N4 0.4(2) . . . .
C12 C11 C15 O2 -179.68(15) . . . .
C12 C11 C15 O3 -0.2(2) . . . .
C13 N4 C9 N3 0.13(18) . . . .
C13 N4 C9 C8 -179.71(12) . . . .
C13 N4 C10 C11 179.95(13) . . . .
C15 C11 C12 O1 -0.6(2) . . . .
C15 C11 C12 C8 178.89(13) . . . .
O4 C16 C17 C18 -7.5(2) . . . .
O5 C16 C17 C18 173.10(13) . . . .
C16 C17 C18 C18 178.98(15) . . . 2_556
