#------------------------------------------------------------------------------
#$Date: 2021-11-06 21:31:29 +0100 (Sat 06 de Nov de 2021) $
#$Revision: 270482 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/09/7060969.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_7060969
loop_
_publ_author_name
'Zhang, Yunan'
'Duan, Yu'
'Su, Jin'
'Liu, Lixin'
'Feng, Yanru'
'Wu, Lili'
'Zhang, Lei'
'Zhang, Yunjie'
'Zou, Dongyu'
'Liu, Yingli'
_publ_section_title
;
 Inspiration for revival of old drugs: improving solubility and avoiding
 hygroscopicity of pipemidic acid by forming two pharmaceutical salts
 based on charge-assisted hydrogen bond recognitions
;
_journal_issue                   42
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              19704
_journal_page_last               19713
_journal_paper_doi               10.1039/D1NJ03314J
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C14 H18 N5 O3, C7 H5 O3, C7 H6 O3, 2(H2 O)'
_chemical_formula_sum            'C28 H33 N5 O11'
_chemical_formula_weight         615.59
_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     direct
_audit_creation_date             2021-06-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-09-20 deposited with the CCDC.	2021-09-21 downloaded from the CCDC.
;
_cell_angle_alpha                106.133(8)
_cell_angle_beta                 103.719(7)
_cell_angle_gamma                96.363(7)
_cell_formula_units_Z            2
_cell_length_a                   8.0857(7)
_cell_length_b                   12.8969(12)
_cell_length_c                   15.2536(13)
_cell_measurement_reflns_used    2789
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.1420
_cell_measurement_theta_min      4.1350
_cell_volume                     1457.6(2)
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.819
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0608
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.819
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11385
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.819
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.533
_diffrn_reflns_theta_min         3.535
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         6655
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1090
_refine_ls_R_factor_gt           0.0610
_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)+(0.0456P)²+0.2682P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1351
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4165
_reflns_number_total             6655
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj03314j2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7060968--7060969.cif.'
_cod_database_code               7060969
_shelx_shelxl_version_number     2018/3
_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   0.988
_shelx_estimated_absorpt_t_min   0.985
_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) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O10(H10A,H10B), O11(H11A,H11B)
2.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)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C17(H17), C18(H18), C19(H19), C24(H24), C26(H26), C27(H27),
 C28(H28)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
O1 O 0.0946(2) 0.77390(13) 0.20894(12) 0.0524(5) Uani 1 1 d . . . . .
O2 O -0.1234(2) 0.68796(14) 0.08161(13) 0.0577(5) Uani 1 1 d . . . . .
H2 H -0.172668 0.624576 0.050998 0.086 Uiso 1 1 calc GR . . . .
O3 O -0.1949(2) 0.48333(13) 0.02080(11) 0.0481(4) Uani 1 1 d . . . . .
N1 N -0.0620(2) -0.03795(14) 0.26156(12) 0.0353(4) Uani 1 1 d . . . . .
H1A H 0.004737 -0.088257 0.253436 0.042 Uiso 1 1 calc R . . . .
H1B H -0.128820 -0.054181 0.296453 0.042 Uiso 1 1 calc R . . . .
N2 N 0.0456(2) 0.09991(14) 0.16300(13) 0.0385(5) Uani 1 1 d . . . . .
N3 N -0.1155(2) 0.18429(14) 0.06628(12) 0.0386(5) Uani 1 1 d . . . . .
N4 N 0.1050(2) 0.28827(14) 0.21085(12) 0.0324(4) Uani 1 1 d . . . . .
N5 N 0.1666(2) 0.47853(14) 0.25824(12) 0.0321(4) Uani 1 1 d . . . . .
C1 C -0.1736(3) -0.04259(18) 0.16731(16) 0.0396(6) Uani 1 1 d . . . . .
H1C H -0.255884 0.005991 0.175928 0.047 Uiso 1 1 calc R . . . .
H1D H -0.238216 -0.116795 0.133811 0.047 Uiso 1 1 calc R . . . .
C2 C -0.0627(3) -0.00819(17) 0.10950(16) 0.0406(6) Uani 1 1 d . . . . .
H2A H 0.010180 -0.061640 0.094591 0.049 Uiso 1 1 calc R . . . .
H2B H -0.136361 -0.005518 0.050174 0.049 Uiso 1 1 calc R . . . .
C3 C 0.0499(3) 0.07234(18) 0.31351(16) 0.0414(6) Uani 1 1 d . . . . .
H3A H 0.124310 0.071466 0.373302 0.050 Uiso 1 1 calc R . . . .
H3B H -0.021690 0.126941 0.327260 0.050 Uiso 1 1 calc R . . . .
C4 C 0.1587(3) 0.10135(19) 0.25308(17) 0.0424(6) Uani 1 1 d . . . . .
H4A H 0.230339 0.173802 0.285683 0.051 Uiso 1 1 calc R . . . .
H4B H 0.234434 0.048748 0.241916 0.051 Uiso 1 1 calc R . . . .
C5 C 0.0119(3) 0.19390(17) 0.14698(15) 0.0328(5) Uani 1 1 d . . . . .
C6 C -0.1414(3) 0.27709(18) 0.05086(15) 0.0381(5) Uani 1 1 d . . . . .
H6 H -0.225794 0.273648 -0.003747 0.046 Uiso 1 1 calc R . . . .
C7 C -0.0506(3) 0.38058(17) 0.11099(14) 0.0309(5) Uani 1 1 d . . . . .
C8 C 0.0726(3) 0.37993(16) 0.19222(14) 0.0288(5) Uani 1 1 d . . . . .
C9 C 0.1390(3) 0.57341(17) 0.24212(15) 0.0332(5) Uani 1 1 d . . . . .
H9 H 0.204335 0.638725 0.286826 0.040 Uiso 1 1 calc R . . . .
C10 C 0.0216(3) 0.57971(17) 0.16455(14) 0.0317(5) Uani 1 1 d . . . . .
C11 C -0.0826(3) 0.48109(17) 0.09336(15) 0.0334(5) Uani 1 1 d . . . . .
C12 C 0.0020(3) 0.68772(18) 0.15397(17) 0.0395(5) Uani 1 1 d . . . . .
C13 C 0.2958(3) 0.47928(19) 0.34571(16) 0.0400(6) Uani 1 1 d . . . . .
H13A H 0.377558 0.548569 0.370955 0.048 Uiso 1 1 calc R . . . .
H13B H 0.359918 0.420841 0.329711 0.048 Uiso 1 1 calc R . . . .
C14 C 0.2128(3) 0.4642(2) 0.42073(17) 0.0520(7) Uani 1 1 d . . . . .
H14A H 0.135915 0.394082 0.397150 0.078 Uiso 1 1 calc GR . . . .
H14B H 0.148513 0.521520 0.436503 0.078 Uiso 1 1 calc GR . . . .
H14C H 0.301101 0.467184 0.476493 0.078 Uiso 1 1 calc GR . . . .
O4 O 0.85519(18) 0.08965(14) 0.57304(13) 0.0489(4) Uani 1 1 d . . . . .
H4 H 0.942144 0.118675 0.563796 0.073 Uiso 1 1 calc GR . . . .
O5 O 0.29296(19) 0.09997(15) 0.65107(12) 0.0512(5) Uani 1 1 d . . . . .
O6 O 0.14563(17) 0.18123(13) 0.55580(12) 0.0438(4) Uani 1 1 d . . . . .
C15 C 0.2805(3) 0.14793(18) 0.58951(15) 0.0339(5) Uani 1 1 d . . . . .
C16 C 0.4346(2) 0.16780(16) 0.55368(14) 0.0290(5) Uani 1 1 d . . . . .
C17 C 0.4357(3) 0.23312(18) 0.49492(15) 0.0359(5) Uani 1 1 d . . . . .
H17 H 0.340850 0.265425 0.477958 0.043 Uiso 1 1 calc R . . . .
C18 C 0.5778(3) 0.24974(19) 0.46196(16) 0.0427(6) Uani 1 1 d . . . . .
H18 H 0.577691 0.292843 0.422155 0.051 Uiso 1 1 calc R . . . .
C19 C 0.7200(3) 0.20350(19) 0.48707(16) 0.0385(5) Uani 1 1 d . . . . .
H19 H 0.815197 0.215407 0.464380 0.046 Uiso 1 1 calc R . . . .
C20 C 0.7209(2) 0.13926(17) 0.54617(15) 0.0317(5) Uani 1 1 d . . . . .
C21 C 0.5776(3) 0.12143(18) 0.57887(15) 0.0322(5) Uani 1 1 d . . . . .
H21 H 0.577(2) 0.0716(17) 0.6155(14) 0.033(6) Uiso 1 1 d . . . . .
O7 O -0.5525(3) 0.18112(17) 0.11507(16) 0.0772(7) Uani 1 1 d . . . . .
H7 H -0.555(5) 0.101(4) 0.109(3) 0.131(14) Uiso 1 1 d . . . . .
O8 O -0.3295(3) 0.19727(15) 0.23818(14) 0.0710(6) Uani 1 1 d . . . . .
O9 O -0.1309(2) 0.60353(16) 0.38814(13) 0.0580(5) Uani 1 1 d . . . . .
H9A H -0.137(4) 0.675(3) 0.400(2) 0.106(13) Uiso 1 1 d . . . . .
C22 C -0.4231(3) 0.2386(2) 0.18984(19) 0.0482(6) Uani 1 1 d . . . . .
C23 C -0.4035(3) 0.35943(19) 0.20734(17) 0.0418(6) Uani 1 1 d . . . . .
C24 C -0.2801(3) 0.42771(19) 0.28844(16) 0.0404(5) Uani 1 1 d . . . . .
H24 H -0.213411 0.397654 0.330081 0.048 Uiso 1 1 calc R . . . .
C25 C -0.2556(3) 0.54051(19) 0.30773(17) 0.0405(6) Uani 1 1 d . . . . .
C26 C -0.3543(3) 0.5846(2) 0.24505(18) 0.0461(6) Uani 1 1 d . . . . .
H26 H -0.337654 0.660361 0.257236 0.055 Uiso 1 1 calc R . . . .
C27 C -0.4775(3) 0.5160(2) 0.16441(18) 0.0533(7) Uani 1 1 d . . . . .
H27 H -0.544002 0.545956 0.122612 0.064 Uiso 1 1 calc R . . . .
C28 C -0.5027(3) 0.4037(2) 0.14531(18) 0.0512(7) Uani 1 1 d . . . . .
H28 H -0.586050 0.357952 0.090950 0.061 Uiso 1 1 calc R . . . .
O10 O -0.4020(3) 0.03007(16) -0.08080(16) 0.0830(7) Uani 1 1 d . . . . .
H10A H -0.320529 0.068852 -0.032196 0.124 Uiso 1 1 d G . . . .
H10B H -0.410892 0.067875 -0.118717 0.124 Uiso 1 1 d G . . . .
O11 O -0.4288(3) 0.1639(3) -0.18928(15) 0.0979(9) Uani 1 1 d . . . . .
H11A H -0.339450 0.184507 -0.204798 0.147 Uiso 1 1 d G . . . .
H11B H -0.511141 0.146348 -0.240254 0.147 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'
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
_geom_angle_publ_flag
C12 O2 H2 109.5 . . ?
H1A N1 H1B 107.9 . . ?
C1 N1 H1A 109.2 . . ?
C1 N1 H1B 109.2 . . ?
C1 N1 C3 112.10(16) . . ?
C3 N1 H1A 109.2 . . ?
C3 N1 H1B 109.2 . . ?
C4 N2 C2 112.32(17) . . ?
C5 N2 C2 124.04(19) . . ?
C5 N2 C4 120.93(18) . . ?
C6 N3 C5 115.49(18) . . ?
C8 N4 C5 116.35(18) . . ?
C8 N5 C13 120.32(17) . . ?
C9 N5 C8 119.20(18) . . ?
C9 N5 C13 120.48(17) . . ?
N1 C1 H1C 109.7 . . ?
N1 C1 H1D 109.7 . . ?
N1 C1 C2 109.85(17) . . ?
H1C C1 H1D 108.2 . . ?
C2 C1 H1C 109.7 . . ?
C2 C1 H1D 109.7 . . ?
N2 C2 C1 109.94(18) . . ?
N2 C2 H2A 109.7 . . ?
N2 C2 H2B 109.7 . . ?
C1 C2 H2A 109.7 . . ?
C1 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
N1 C3 H3A 109.8 . . ?
N1 C3 H3B 109.8 . . ?
N1 C3 C4 109.17(18) . . ?
H3A C3 H3B 108.3 . . ?
C4 C3 H3A 109.8 . . ?
C4 C3 H3B 109.8 . . ?
N2 C4 C3 109.18(18) . . ?
N2 C4 H4A 109.8 . . ?
N2 C4 H4B 109.8 . . ?
C3 C4 H4A 109.8 . . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.3 . . ?
N2 C5 N3 116.85(19) . . ?
N4 C5 N2 117.45(19) . . ?
N4 C5 N3 125.7(2) . . ?
N3 C6 H6 117.9 . . ?
N3 C6 C7 124.3(2) . . ?
C7 C6 H6 117.9 . . ?
C6 C7 C8 114.91(19) . . ?
C6 C7 C11 123.34(19) . . ?
C8 C7 C11 121.73(18) . . ?
N4 C8 N5 117.09(18) . . ?
N4 C8 C7 123.24(18) . . ?
N5 C8 C7 119.67(19) . . ?
N5 C9 H9 118.0 . . ?
N5 C9 C10 124.04(19) . . ?
C10 C9 H9 118.0 . . ?
C9 C10 C11 120.1(2) . . ?
C9 C10 C12 119.56(19) . . ?
C11 C10 C12 120.3(2) . . ?
O3 C11 C7 122.62(19) . . ?
O3 C11 C10 122.2(2) . . ?
C7 C11 C10 115.22(19) . . ?
O1 C12 O2 120.7(2) . . ?
O1 C12 C10 123.2(2) . . ?
O2 C12 C10 116.1(2) . . ?
N5 C13 H13A 109.1 . . ?
N5 C13 H13B 109.1 . . ?
N5 C13 C14 112.30(18) . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
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 . . ?
C20 O4 H4 109.5 . . ?
O5 C15 O6 124.0(2) . . ?
O5 C15 C16 118.26(19) . . ?
O6 C15 C16 117.8(2) . . ?
C17 C16 C15 120.45(19) . . ?
C21 C16 C15 120.30(19) . . ?
C21 C16 C17 119.25(19) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.7(2) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 121.0(2) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.7(2) . . ?
C20 C19 H19 120.1 . . ?
O4 C20 C19 123.21(18) . . ?
O4 C20 C21 117.23(19) . . ?
C19 C20 C21 119.5(2) . . ?
C16 C21 C20 120.8(2) . . ?
C16 C21 H21 121.0(12) . . ?
C20 C21 H21 118.1(12) . . ?
C22 O7 H7 107(2) . . ?
C25 O9 H9A 111(2) . . ?
O7 C22 C23 113.2(2) . . ?
O8 C22 O7 123.2(2) . . ?
O8 C22 C23 123.6(2) . . ?
C24 C23 C22 117.8(2) . . ?
C28 C23 C22 122.1(2) . . ?
C28 C23 C24 120.1(2) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.2(2) . . ?
C25 C24 H24 119.9 . . ?
O9 C25 C24 117.6(2) . . ?
O9 C25 C26 122.9(2) . . ?
C24 C25 C26 119.6(2) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 C25 119.9(2) . . ?
C27 C26 H26 120.0 . . ?
C26 C27 H27 119.7 . . ?
C28 C27 C26 120.6(2) . . ?
C28 C27 H27 119.7 . . ?
C23 C28 H28 120.2 . . ?
C27 C28 C23 119.6(2) . . ?
C27 C28 H28 120.2 . . ?
H10A O10 H10B 104.5 . . ?
H11A O11 H11B 104.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C12 1.224(3) . ?
O2 H2 0.8200 . ?
O2 C12 1.311(3) . ?
O3 C11 1.264(2) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 C1 1.486(3) . ?
N1 C3 1.489(3) . ?
N2 C2 1.461(3) . ?
N2 C4 1.453(3) . ?
N2 C5 1.345(3) . ?
N3 C5 1.370(3) . ?
N3 C6 1.312(3) . ?
N4 C5 1.337(2) . ?
N4 C8 1.329(3) . ?
N5 C8 1.386(2) . ?
N5 C9 1.345(3) . ?
N5 C13 1.484(3) . ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C1 C2 1.511(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.506(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C6 H6 0.9300 . ?
C6 C7 1.394(3) . ?
C7 C8 1.396(3) . ?
C7 C11 1.433(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.358(3) . ?
C10 C11 1.438(3) . ?
C10 C12 1.468(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.502(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
O4 H4 0.8200 . ?
O4 C20 1.358(2) . ?
O5 C15 1.251(3) . ?
O6 C15 1.264(2) . ?
C15 C16 1.500(3) . ?
C16 C17 1.391(3) . ?
C16 C21 1.383(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.378(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.376(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.383(3) . ?
C20 C21 1.386(3) . ?
C21 H21 0.96(2) . ?
O7 H7 1.01(4) . ?
O7 C22 1.318(3) . ?
O8 C22 1.202(3) . ?
O9 H9A 0.90(4) . ?
O9 C25 1.364(3) . ?
C22 C23 1.489(3) . ?
C23 C24 1.384(3) . ?
C23 C28 1.381(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.383(3) . ?
C25 C26 1.384(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.381(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.377(4) . ?
C28 H28 0.9300 . ?
O10 H10A 0.8504 . ?
O10 H10B 0.8498 . ?
O11 H11A 0.8500 . ?
O11 H11B 0.8499 . ?
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
_geom_torsion_publ_flag
N1 C1 C2 N2 -54.7(2) . . . . ?
N1 C3 C4 N2 58.2(2) . . . . ?
N3 C6 C7 C8 -0.8(3) . . . . ?
N3 C6 C7 C11 -179.2(2) . . . . ?
N5 C9 C10 C11 0.0(3) . . . . ?
N5 C9 C10 C12 -179.99(19) . . . . ?
C1 N1 C3 C4 -57.0(2) . . . . ?
C2 N2 C4 C3 -60.9(2) . . . . ?
C2 N2 C5 N3 -10.7(3) . . . . ?
C2 N2 C5 N4 169.28(19) . . . . ?
C3 N1 C1 C2 55.3(2) . . . . ?
C4 N2 C2 C1 59.1(2) . . . . ?
C4 N2 C5 N3 -170.57(19) . . . . ?
C4 N2 C5 N4 9.4(3) . . . . ?
C5 N2 C2 C1 -102.3(2) . . . . ?
C5 N2 C4 C3 101.2(2) . . . . ?
C5 N3 C6 C7 -0.9(3) . . . . ?
C5 N4 C8 N5 179.27(17) . . . . ?
C5 N4 C8 C7 -0.2(3) . . . . ?
C6 N3 C5 N2 -177.78(19) . . . . ?
C6 N3 C5 N4 2.3(3) . . . . ?
C6 C7 C8 N4 1.3(3) . . . . ?
C6 C7 C8 N5 -178.09(18) . . . . ?
C6 C7 C11 O3 -0.9(3) . . . . ?
C6 C7 C11 C10 178.7(2) . . . . ?
C8 N4 C5 N2 178.28(18) . . . . ?
C8 N4 C5 N3 -1.7(3) . . . . ?
C8 N5 C9 C10 0.8(3) . . . . ?
C8 N5 C13 C14 -80.0(2) . . . . ?
C8 C7 C11 O3 -179.2(2) . . . . ?
C8 C7 C11 C10 0.4(3) . . . . ?
C9 N5 C8 N4 179.58(18) . . . . ?
C9 N5 C8 C7 -0.9(3) . . . . ?
C9 N5 C13 C14 99.9(2) . . . . ?
C9 C10 C11 O3 179.0(2) . . . . ?
C9 C10 C11 C7 -0.6(3) . . . . ?
C9 C10 C12 O1 4.9(3) . . . . ?
C9 C10 C12 O2 -174.5(2) . . . . ?
C11 C7 C8 N4 179.76(19) . . . . ?
C11 C7 C8 N5 0.3(3) . . . . ?
C11 C10 C12 O1 -175.1(2) . . . . ?
C11 C10 C12 O2 5.5(3) . . . . ?
C12 C10 C11 O3 -1.0(3) . . . . ?
C12 C10 C11 C7 179.38(19) . . . . ?
C13 N5 C8 N4 -0.5(3) . . . . ?
C13 N5 C8 C7 178.94(19) . . . . ?
C13 N5 C9 C10 -179.09(19) . . . . ?
O4 C20 C21 C16 -179.13(19) . . . . ?
O5 C15 C16 C17 -171.5(2) . . . . ?
O5 C15 C16 C21 8.4(3) . . . . ?
O6 C15 C16 C17 8.2(3) . . . . ?
O6 C15 C16 C21 -171.91(19) . . . . ?
C15 C16 C17 C18 -179.44(19) . . . . ?
C15 C16 C21 C20 -179.99(19) . . . . ?
C16 C17 C18 C19 -0.7(3) . . . . ?
C17 C16 C21 C20 -0.1(3) . . . . ?
C17 C18 C19 C20 0.1(3) . . . . ?
C18 C19 C20 O4 179.1(2) . . . . ?
C18 C19 C20 C21 0.5(3) . . . . ?
C19 C20 C21 C16 -0.5(3) . . . . ?
C21 C16 C17 C18 0.7(3) . . . . ?
O7 C22 C23 C24 175.0(2) . . . . ?
O7 C22 C23 C28 -5.5(3) . . . . ?
O8 C22 C23 C24 -5.8(4) . . . . ?
O8 C22 C23 C28 173.7(3) . . . . ?
O9 C25 C26 C27 179.4(2) . . . . ?
C22 C23 C24 C25 179.5(2) . . . . ?
C22 C23 C28 C27 -179.2(2) . . . . ?
C23 C24 C25 O9 -179.3(2) . . . . ?
C23 C24 C25 C26 -0.5(3) . . . . ?
C24 C23 C28 C27 0.3(4) . . . . ?
C24 C25 C26 C27 0.7(4) . . . . ?
C25 C26 C27 C28 -0.3(4) . . . . ?
C26 C27 C28 C23 -0.2(4) . . . . ?
C28 C23 C24 C25 0.0(3) . . . . ?
