#------------------------------------------------------------------------------
#$Date: 2023-05-06 13:45:19 +0300 (Sat, 06 May 2023) $
#$Revision: 283579 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/27/2022719.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_2022719
loop_
_publ_author_name
'Archana, Sreeramapura D.'
'Foro, Sabine'
'Yathirajan, Hemmige S.'
'Kiran Kumar, Haruvegowda'
'Balerao, Rishik'
'Butcher, Ray J.'
_publ_section_title
;
 Syntheses, crystal structures and Hirshfeld surface analysis of three
 salts of 1-(4-nitro-phenyl)-piperazine.
;
_journal_issue                   'Pt 4'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              373
_journal_page_last               379
_journal_paper_doi               10.1107/S2056989023002517
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C10 H14 N3 O2 +, C7 H3 N2 O6 -'
_chemical_formula_moiety         'C10 H14 N3 O2 +, C7 H3 N2 O6 -'
_chemical_formula_sum            'C17 H17 N5 O8'
_chemical_formula_weight         419.35
_chemical_name_systematic
;
4-(4-Nitrophenyl)piperazin-1-ium 3,5-dinitrobenzoate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 136.55(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.953(6)
_cell_length_b                   8.1422(6)
_cell_length_c                   24.657(5)
_cell_measurement_reflns_used    4154
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.70
_cell_measurement_theta_min      2.63
_cell_volume                     3859(3)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis CCD  (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur with Sapphire CCD
;
_diffrn_measurement_method
;
Rotation method data acquisition using omega scans.
;
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0153
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            8107
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.743
_diffrn_reflns_theta_min         2.641
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62057
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_description       prism
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.480
_exptl_crystal_size_min          0.400
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.236
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4119
_refine_ls_number_restraints     262
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0440
_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)+(0.0543P)²+1.7099P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1189
_reflns_number_gt                2838
_reflns_number_total             4119
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            vm2276sup1.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 2022717--2022719.cif.'
_cod_original_cell_volume        3859(2)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2022719
_cod_database_fobs_code          2022719
_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_min   0.946
_shelx_estimated_absorpt_t_max   0.955
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.02612(8) 0.1284(2) 0.33993(9) 0.0580(4) Uani d 1 . .
N N2 0.02315(7) -0.0150(2) 0.44281(9) 0.0452(4) Uani d 1 . .
H H21 -0.0246(11) -0.041(2) 0.4078(11) 0.054(5) Uiso d 1 . .
H H22 0.0488(10) -0.044(2) 0.4941(13) 0.060(6) Uiso d 1 . .
O O1 0.29131(19) 0.2691(7) 0.4152(3) 0.0936(12) Uani d 0.806(10) A 1
O O2 0.28193(17) 0.5004(6) 0.4502(2) 0.0809(12) Uani d 0.806(10) A 1
N N3 0.26170(14) 0.3612(7) 0.42375(18) 0.0631(11) Uani d 0.806(10) A 1
C C1 0.08449(14) 0.1834(4) 0.3603(2) 0.0484(8) Uani d 0.806(10) A 1
C C2 0.12478(14) 0.0767(5) 0.36260(19) 0.0547(7) Uani d 0.806(10) A 1
H H2A 0.112973 -0.033824 0.350722 0.066 Uiso calc 0.806(10) A 1
C C3 0.18272(12) 0.1354(5) 0.38267(16) 0.0554(8) Uani d 0.806(10) A 1
H H3A 0.209682 0.064018 0.384227 0.067 Uiso calc 0.806(10) A 1
C C4 0.20037(11) 0.3006(5) 0.40042(16) 0.0508(8) Uani d 0.806(10) A 1
C C5 0.16008(13) 0.4073(4) 0.3981(2) 0.0621(8) Uani d 0.806(10) A 1
H H5A 0.171890 0.517846 0.409976 0.075 Uiso calc 0.806(10) A 1
C C6 0.10214(14) 0.3487(4) 0.3780(2) 0.0613(8) Uani d 0.806(10) A 1
H H6A 0.075181 0.420007 0.376471 0.074 Uiso calc 0.806(10) A 1
O O1A 0.2969(7) 0.342(2) 0.4346(10) 0.082(3) Uani d 0.194(10) A 2
O O2A 0.2788(8) 0.575(2) 0.4647(10) 0.092(4) Uani d 0.194(10) A 2
N N3A 0.2640(8) 0.436(2) 0.4386(12) 0.067(2) Uani d 0.194(10) A 2
C C1A 0.0900(6) 0.2138(18) 0.3708(9) 0.0517(19) Uani d 0.194(10) A 2
C C2A 0.1283(6) 0.1262(16) 0.3643(9) 0.0519(18) Uani d 0.194(10) A 2
H H2AA 0.116265 0.018417 0.346160 0.062 Uiso calc 0.194(10) A 2
C C3A 0.1845(6) 0.1997(19) 0.3848(7) 0.0519(17) Uani d 0.194(10) A 2
H H3AA 0.210172 0.141125 0.380427 0.062 Uiso calc 0.194(10) A 2
C C4A 0.2025(5) 0.3609(18) 0.4119(7) 0.0608(19) Uani d 0.194(10) A 2
C C5A 0.1642(6) 0.4485(14) 0.4184(8) 0.064(2) Uani d 0.194(10) A 2
H H5AA 0.176195 0.556282 0.436505 0.077 Uiso calc 0.194(10) A 2
C C6A 0.1079(6) 0.3750(17) 0.3979(9) 0.062(2) Uani d 0.194(10) A 2
H H6AA 0.082288 0.433576 0.402238 0.075 Uiso calc 0.194(10) A 2
C C7 0.01491(10) -0.0473(3) 0.33759(11) 0.0549(5) Uani d 1 . .
H H7A 0.033495 -0.105603 0.321795 0.066 Uiso calc 1 . .
H H7B -0.034605 -0.069484 0.298825 0.066 Uiso calc 1 . .
C C8 0.04986(8) -0.1082(2) 0.41735(9) 0.0453(4) Uani d 1 . .
H H8A 0.040452 -0.224338 0.414378 0.054 Uiso calc 1 . .
H H8B 0.099796 -0.093615 0.455510 0.054 Uiso calc 1 . .
C C9 0.02899(9) 0.1652(3) 0.44076(12) 0.0566(5) Uani d 1 . .
H H9A 0.077636 0.196839 0.480671 0.068 Uiso calc 1 . .
H H9B 0.006349 0.220270 0.452198 0.068 Uiso calc 1 . .
C C10 -0.00458(10) 0.2165(3) 0.36060(13) 0.0665(6) Uani d 1 . .
H H10A -0.054078 0.193843 0.321442 0.080 Uiso calc 1 . .
H H10B 0.001467 0.333748 0.360480 0.080 Uiso calc 1 . .
O O3 -0.34048(7) 0.22513(19) 0.30638(8) 0.0637(4) Uani d 1 . .
O O4 -0.43333(6) 0.11002(19) 0.19876(9) 0.0728(4) Uani d 1 . .
O O5 -0.43221(7) -0.0409(2) 0.00913(7) 0.0831(5) Uani d 1 . .
O O6 -0.33493(8) -0.1049(2) 0.05113(8) 0.0724(4) Uani d 1 . .
O O7 -0.11517(5) 0.10834(17) 0.40386(6) 0.0513(3) Uani d 1 . .
O O8 -0.11592(5) -0.06375(17) 0.33293(7) 0.0543(3) Uani d 1 . .
N N4 -0.37128(7) 0.14524(19) 0.24700(10) 0.0500(4) Uani d 1 . .
N N5 -0.36882(8) -0.05526(19) 0.06164(8) 0.0563(4) Uani d 1 . .
C C11 -0.22389(7) 0.03229(19) 0.27718(9) 0.0358(4) Uani d 1 . .
C C12 -0.26050(8) 0.0878(2) 0.29183(9) 0.0379(4) Uani d 1 . .
H H12 -0.237068 0.124431 0.341817 0.046 Uiso calc 1 . .
C C13 -0.33255(8) 0.0880(2) 0.23089(10) 0.0411(4) Uani d 1 . .
C C14 -0.36957(8) 0.0396(2) 0.15541(10) 0.0457(4) Uani d 1 . .
H H14 -0.417939 0.040358 0.115159 0.055 Uiso calc 1 . .
C C15 -0.33151(8) -0.0098(2) 0.14243(9) 0.0432(4) Uani d 1 . .
C C16 -0.25940(8) -0.0165(2) 0.20176(9) 0.0398(4) Uani d 1 . .
H H16 -0.235352 -0.053046 0.191140 0.048 Uiso calc 1 . .
C C17 -0.14489(7) 0.0247(2) 0.34377(9) 0.0376(4) 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 0.0033 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'
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
C1 N1 C7 . . 119.6(2) ?
C1 N1 C10 . . 123.3(2) ?
C7 N1 C10 . . 109.32(15) ?
C7 N1 C1A . . 127.9(6) ?
C10 N1 C1A . . 112.1(6) ?
C9 N2 C8 . . 112.95(14) ?
C9 N2 H21 . . 108.0(12) ?
C8 N2 H21 . . 107.8(11) ?
C9 N2 H22 . . 108.0(12) ?
C8 N2 H22 . . 108.5(12) ?
H21 N2 H22 . . 111.6(17) ?
O2 N3 O1 . . 122.9(3) ?
O2 N3 C4 . . 119.0(3) ?
O1 N3 C4 . . 118.1(3) ?
N1 C1 C2 . . 121.22(19) ?
N1 C1 C6 . . 118.78(19) ?
C2 C1 C6 . . 120.0 ?
C3 C2 C1 . . 120.0 ?
C3 C2 H2A . . 120.0 ?
C1 C2 H2A . . 120.0 ?
C2 C3 C4 . . 120.0 ?
C2 C3 H3A . . 120.0 ?
C4 C3 H3A . . 120.0 ?
C5 C4 C3 . . 120.0 ?
C5 C4 N3 . . 119.7(2) ?
C3 C4 N3 . . 120.3(2) ?
C4 C5 C6 . . 120.0 ?
C4 C5 H5A . . 120.0 ?
C6 C5 H5A . . 120.0 ?
C5 C6 C1 . . 120.0 ?
C5 C6 H6A . . 120.0 ?
C1 C6 H6A . . 120.0 ?
O2A N3A O1A . . 128.2(14) ?
O2A N3A C4A . . 117.8(13) ?
O1A N3A C4A . . 114.0(13) ?
C2A C1A C6A . . 120.0 ?
C2A C1A N1 . . 115.7(8) ?
C6A C1A N1 . . 124.0(8) ?
C1A C2A C3A . . 120.0 ?
C1A C2A H2AA . . 120.0 ?
C3A C2A H2AA . . 120.0 ?
C4A C3A C2A . . 120.0 ?
C4A C3A H3AA . . 120.0 ?
C2A C3A H3AA . . 120.0 ?
C3A C4A C5A . . 120.0 ?
C3A C4A N3A . . 120.6(8) ?
C5A C4A N3A . . 119.3(8) ?
C6A C5A C4A . . 120.0 ?
C6A C5A H5AA . . 120.0 ?
C4A C5A H5AA . . 120.0 ?
C5A C6A C1A . . 120.0 ?
C5A C6A H6AA . . 120.0 ?
C1A C6A H6AA . . 120.0 ?
N1 C7 C8 . . 110.72(15) ?
N1 C7 H7A . . 109.5 ?
C8 C7 H7A . . 109.5 ?
N1 C7 H7B . . 109.5 ?
C8 C7 H7B . . 109.5 ?
H7A C7 H7B . . 108.1 ?
N2 C8 C7 . . 109.52(15) ?
N2 C8 H8A . . 109.8 ?
C7 C8 H8A . . 109.8 ?
N2 C8 H8B . . 109.8 ?
C7 C8 H8B . . 109.8 ?
H8A C8 H8B . . 108.2 ?
N2 C9 C10 . . 109.91(17) ?
N2 C9 H9A . . 109.7 ?
C10 C9 H9A . . 109.7 ?
N2 C9 H9B . . 109.7 ?
C10 C9 H9B . . 109.7 ?
H9A C9 H9B . . 108.2 ?
N1 C10 C9 . . 110.88(16) ?
N1 C10 H10A . . 109.5 ?
C9 C10 H10A . . 109.5 ?
N1 C10 H10B . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 108.1 ?
O3 N4 O4 . . 123.95(17) ?
O3 N4 C13 . . 118.51(14) ?
O4 N4 C13 . . 117.53(17) ?
O6 N5 O5 . . 123.96(17) ?
O6 N5 C15 . . 118.28(15) ?
O5 N5 C15 . . 117.76(19) ?
C12 C11 C16 . . 119.88(14) ?
C12 C11 C17 . . 120.03(14) ?
C16 C11 C17 . . 120.08(15) ?
C11 C12 C13 . . 119.02(15) ?
C11 C12 H12 . . 120.5 ?
C13 C12 H12 . . 120.5 ?
C14 C13 C12 . . 122.68(17) ?
C14 C13 N4 . . 118.49(15) ?
C12 C13 N4 . . 118.82(16) ?
C15 C14 C13 . . 116.72(15) ?
C15 C14 H14 . . 121.6 ?
C13 C14 H14 . . 121.6 ?
C14 C15 C16 . . 122.91(16) ?
C14 C15 N5 . . 118.67(15) ?
C16 C15 N5 . . 118.41(17) ?
C11 C16 C15 . . 118.74(16) ?
C11 C16 H16 . . 120.6 ?
C15 C16 H16 . . 120.6 ?
O8 C17 O7 . . 126.27(14) ?
O8 C17 C11 . . 116.84(14) ?
O7 C17 C11 . . 116.90(15) ?
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
N1 C1 . 1.388(3) ?
N1 C7 . 1.457(3) ?
N1 C10 . 1.465(3) ?
N1 C1A . 1.508(9) ?
N2 C9 . 1.481(3) ?
N2 C8 . 1.486(2) ?
N2 H21 . 0.95(2) ?
N2 H22 . 0.92(2) ?
O1 N3 . 1.243(4) ?
O2 N3 . 1.222(4) ?
N3 C4 . 1.443(3) ?
C1 C2 . 1.3900 ?
C1 C6 . 1.3900 ?
C2 C3 . 1.3900 ?
C2 H2A . 0.9300 ?
C3 C4 . 1.3900 ?
C3 H3A . 0.9300 ?
C4 C5 . 1.3900 ?
C5 C6 . 1.3900 ?
C5 H5A . 0.9300 ?
C6 H6A . 0.9300 ?
O1A N3A . 1.251(16) ?
O2A N3A . 1.217(15) ?
N3A C4A . 1.455(12) ?
C1A C2A . 1.3900 ?
C1A C6A . 1.3900 ?
C2A C3A . 1.3900 ?
C2A H2AA . 0.9300 ?
C3A C4A . 1.3900 ?
C3A H3AA . 0.9300 ?
C4A C5A . 1.3900 ?
C5A C6A . 1.3900 ?
C5A H5AA . 0.9300 ?
C6A H6AA . 0.9300 ?
C7 C8 . 1.509(3) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.506(3) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
O3 N4 . 1.216(2) ?
O4 N4 . 1.229(2) ?
O5 N5 . 1.224(2) ?
O6 N5 . 1.219(2) ?
O7 C17 . 1.250(2) ?
O8 C17 . 1.2491(19) ?
N4 C13 . 1.473(2) ?
N5 C15 . 1.475(2) ?
C11 C12 . 1.385(2) ?
C11 C16 . 1.386(2) ?
C11 C17 . 1.520(2) ?
C12 C13 . 1.386(2) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.376(2) ?
C14 C15 . 1.375(3) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.387(2) ?
C16 H16 . 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
_geom_hbond_publ_flag
N2 H21 O8 . 0.95(2) 1.77(2) 2.705(3) 170.7(17) yes
N2 H22 O7 5_556 0.92(2) 1.81(2) 2.715(3) 166.4(18) yes
C8 H8A O4 4_445 0.97 2.54 3.245(3) 130 yes
C8 H8B O2 7_556 0.97 2.40 3.354(4) 168 yes
C8 H8B O2A 7_556 0.97 2.39 3.353(16) 172 yes
C9 H9A O1 7_556 0.97 2.54 3.497(5) 171 yes
C9 H9A O1A 7_556 0.97 2.47 3.378(14) 155 yes
C10 H10B O4 4_455 0.97 2.60 3.425(3) 143 yes
C12 H12 O2 3_445 0.93 2.53 3.231(4) 133 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 N1 C1 C2 . . . . 13.5(3) ?
C10 N1 C1 C2 . . . . 159.33(19) ?
C7 N1 C1 C6 . . . . -166.94(18) ?
C10 N1 C1 C6 . . . . -21.1(3) ?
N1 C1 C2 C3 . . . . 179.6(3) ?
C6 C1 C2 C3 . . . . 0.0 ?
C1 C2 C3 C4 . . . . 0.0 ?
C2 C3 C4 C5 . . . . 0.0 ?
C2 C3 C4 N3 . . . . 178.0(2) ?
O2 N3 C4 C5 . . . . 8.8(4) ?
O1 N3 C4 C5 . . . . -170.6(3) ?
O2 N3 C4 C3 . . . . -169.2(3) ?
O1 N3 C4 C3 . . . . 11.4(4) ?
C3 C4 C5 C6 . . . . 0.0 ?
N3 C4 C5 C6 . . . . -178.0(2) ?
C4 C5 C6 C1 . . . . 0.0 ?
N1 C1 C6 C5 . . . . -179.6(3) ?
C2 C1 C6 C5 . . . . 0.0 ?
C7 N1 C1A C2A . . . . 30.4(11) ?
C10 N1 C1A C2A . . . . 170.6(5) ?
C7 N1 C1A C6A . . . . -155.4(6) ?
C10 N1 C1A C6A . . . . -15.1(10) ?
C6A C1A C2A C3A . . . . 0.0 ?
N1 C1A C2A C3A . . . . 174.5(11) ?
C1A C2A C3A C4A . . . . 0.0 ?
C2A C3A C4A C5A . . . . 0.0 ?
C2A C3A C4A N3A . . . . 175.8(13) ?
O2A N3A C4A C3A . . . . -177.1(15) ?
O1A N3A C4A C3A . . . . 0(2) ?
O2A N3A C4A C5A . . . . -1(2) ?
O1A N3A C4A C5A . . . . 175.8(13) ?
C3A C4A C5A C6A . . . . 0.0 ?
N3A C4A C5A C6A . . . . -175.9(13) ?
C4A C5A C6A C1A . . . . 0.0 ?
C2A C1A C6A C5A . . . . 0.0 ?
N1 C1A C6A C5A . . . . -174.0(12) ?
C1 N1 C7 C8 . . . . 88.7(2) ?
C10 N1 C7 C8 . . . . -61.5(2) ?
C1A N1 C7 C8 . . . . 79.6(8) ?
C9 N2 C8 C7 . . . . -53.44(19) ?
N1 C7 C8 N2 . . . . 57.24(19) ?
C8 N2 C9 C10 . . . . 53.10(19) ?
C1 N1 C10 C9 . . . . -87.8(3) ?
C7 N1 C10 C9 . . . . 61.0(2) ?
C1A N1 C10 C9 . . . . -86.7(7) ?
N2 C9 C10 N1 . . . . -56.3(2) ?
C16 C11 C12 C13 . . . . 2.3(2) ?
C17 C11 C12 C13 . . . . -177.66(15) ?
C11 C12 C13 C14 . . . . -2.0(3) ?
C11 C12 C13 N4 . . . . 179.25(15) ?
O3 N4 C13 C14 . . . . -161.90(16) ?
O4 N4 C13 C14 . . . . 17.5(2) ?
O3 N4 C13 C12 . . . . 16.9(2) ?
O4 N4 C13 C12 . . . . -163.67(16) ?
C12 C13 C14 C15 . . . . -0.1(3) ?
N4 C13 C14 C15 . . . . 178.72(15) ?
C13 C14 C15 C16 . . . . 1.9(3) ?
C13 C14 C15 N5 . . . . -177.15(15) ?
O6 N5 C15 C14 . . . . -177.23(17) ?
O5 N5 C15 C14 . . . . 2.7(3) ?
O6 N5 C15 C16 . . . . 3.7(3) ?
O5 N5 C15 C16 . . . . -176.40(17) ?
C12 C11 C16 C15 . . . . -0.6(2) ?
C17 C11 C16 C15 . . . . 179.33(15) ?
C14 C15 C16 C11 . . . . -1.5(3) ?
N5 C15 C16 C11 . . . . 177.46(15) ?
C12 C11 C17 O8 . . . . 161.97(15) ?
C16 C11 C17 O8 . . . . -18.0(2) ?
C12 C11 C17 O7 . . . . -18.5(2) ?
C16 C11 C17 O7 . . . . 161.58(15) ?
