#------------------------------------------------------------------------------
#$Date: 2023-07-06 21:18:41 +0300 (Thu, 06 Jul 2023) $
#$Revision: 285053 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/27/2022772.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_2022772
loop_
_publ_author_name
'Palacios Rodríguez, José Carlos'
'Mendoza, Angel'
'Sosa Rivadeneyra, Martha'
'Bernès, Sylvain'
_publ_section_title
;
 2-[3-(1H-Benzimidazol-2-yl)prop-yl]-1H-benzimidazol-3-ium
 3,4,5-tri-hydroxy-benzoate-1,3-bis-(1H-benzimidazol-2-yl)propane-ethyl
 acetate (2/1/2.94): co-crystallization between a salt, a neutral
 mol-ecule and a solvent.
;
_journal_coeditor_code           WM5683
_journal_issue                   'Pt 6'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              562
_journal_page_last               566
_journal_paper_doi               10.1107/S2056989023004279
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          '2C17 H17 N4 +, 2C7 H5 O5 -, C17 H16 N4'
_chemical_formula_moiety         '2(C17 H17 N4 +), 2(C7 H5 O5 -), C17 H16 N4'
_chemical_formula_sum            'C65 H60 N12 O10'
_chemical_formula_weight         1169.25
_chemical_name_systematic
;
2-[3-(1H-Benzimidazol-2-yl)propyl]-1H-benzimidazol-3-ium
3,4,5-trihydroxybenzoate--1,3-bis(1H-benzimidazol-2-yl)propane--ethyl
acetate (2/1/2.94)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 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                 105.2162(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.82625(15)
_cell_length_b                   16.73298(17)
_cell_length_c                   26.7833(3)
_cell_measurement_reflns_used    53060
_cell_measurement_temperature    295.0(10)
_cell_measurement_theta_max      33.6450
_cell_measurement_theta_min      1.5200
_cell_volume                     7276.56(13)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2022)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2022)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2022)
;
_computing_molecular_graphics
;
XP in SHELXTL-Plus (Sheldrick, 2008), Mercury (Macrae et al.,
2020) and
CrystalExplorer (Spackman et al.,  2021)
;
_computing_publication_material
;
PublCif (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018/2 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      295.0(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5564
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            188774
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.507
_diffrn_reflns_theta_min         1.576
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.761
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2022)
;
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.067
_exptl_crystal_description       block
_exptl_crystal_F_000             2456
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.480
_exptl_crystal_size_min          0.370
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.181
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     414
_refine_ls_number_reflns         11088
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0494
_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)+(0.0782P)²+1.8337P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1373
_refine_ls_wR_factor_ref         0.1493
_reflns_number_gt                8064
_reflns_number_total             11088
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wm5683sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2022772.cif.'
_cod_original_cell_volume        7276.57(14)
_cod_original_sg_symbol_H-M      'I 2/a'
_cod_database_code               2022772
_cod_database_fobs_code          2022772
_shelx_estimated_absorpt_t_min   0.956
_shelx_estimated_absorpt_t_max   0.973
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -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 0.62719(6) 0.20714(6) 0.69126(4) 0.0409(2) Uani d 1 . .
N N2 0.70426(6) 0.31366(7) 0.68709(4) 0.0415(2) Uani d 1 . .
H H2 0.7153(9) 0.3686(10) 0.6889(6) 0.050 Uiso d 1 . .
N N3 0.29155(6) 0.28875(6) 0.65905(4) 0.0410(2) Uani d 1 . .
H H3 0.2821(9) 0.3375(10) 0.6465(6) 0.049 Uiso d 1 . .
N N4 0.35419(6) 0.17996(6) 0.69126(5) 0.0456(3) Uani d 1 . .
H H4 0.3956(10) 0.1491(10) 0.7050(6) 0.055 Uiso d 1 . .
C C1 0.63565(6) 0.28528(7) 0.69822(4) 0.0369(2) Uani d 1 . .
C C2 0.69506(7) 0.18377(8) 0.67405(5) 0.0417(3) Uani d 1 . .
C C3 0.71780(10) 0.10890(10) 0.66007(7) 0.0588(4) Uani d 1 . .
H H3A 0.686161 0.063838 0.661591 0.071 Uiso calc 1 . .
C C4 0.78909(12) 0.10380(12) 0.64384(8) 0.0715(5) Uani d 1 . .
H H4A 0.805713 0.054293 0.634429 0.086 Uiso calc 1 . .
C C5 0.83663(11) 0.17096(12) 0.64124(7) 0.0710(5) Uani d 1 . .
H H5 0.884062 0.165163 0.629939 0.085 Uiso calc 1 . .
C C6 0.81553(9) 0.24544(11) 0.65486(6) 0.0586(4) Uani d 1 . .
H H6 0.847519 0.290187 0.653195 0.070 Uiso calc 1 . .
C C7 0.74379(7) 0.25066(8) 0.67130(5) 0.0420(3) Uani d 1 . .
C C8 0.58072(7) 0.34195(8) 0.71577(6) 0.0454(3) Uani d 1 . .
H H8A 0.570693 0.387335 0.692415 0.055 Uiso calc 1 . .
H H8B 0.609617 0.361623 0.749748 0.055 Uiso calc 1 . .
C C9 0.49824(7) 0.30894(8) 0.71883(5) 0.0458(3) Uani d 1 . .
H H9A 0.469890 0.349272 0.733691 0.055 Uiso calc 1 . .
H H9B 0.507561 0.263106 0.741808 0.055 Uiso calc 1 . .
C C10 0.44301(7) 0.28374(8) 0.66621(6) 0.0454(3) Uani d 1 . .
H H10A 0.432614 0.329527 0.643194 0.055 Uiso calc 1 . .
H H10B 0.471005 0.243466 0.651070 0.055 Uiso calc 1 . .
C C11 0.36365(7) 0.25125(7) 0.67136(5) 0.0410(3) Uani d 1 . .
C C12 0.23293(7) 0.24029(7) 0.67147(5) 0.0403(3) Uani d 1 . .
C C13 0.14945(8) 0.25199(9) 0.66602(6) 0.0542(4) Uani d 1 . .
H H13 0.123234 0.299434 0.653072 0.065 Uiso calc 1 . .
C C14 0.10775(9) 0.18973(11) 0.68079(7) 0.0650(4) Uani d 1 . .
H H14 0.051424 0.194600 0.677015 0.078 Uiso calc 1 . .
C C15 0.14755(9) 0.11917(10) 0.70137(7) 0.0637(4) Uani d 1 . .
H H15 0.116961 0.078516 0.711040 0.076 Uiso calc 1 . .
C C16 0.23059(8) 0.10804(9) 0.70774(6) 0.0536(3) Uani d 1 . .
H H16 0.257062 0.061314 0.721899 0.064 Uiso calc 1 . .
C C17 0.27263(7) 0.17010(8) 0.69195(5) 0.0422(3) Uani d 1 . .
N N5 0.45349(6) 0.41770(7) 0.53870(4) 0.0448(3) Uani d 1 . .
N N6 0.41648(6) 0.41115(7) 0.45294(4) 0.0386(2) Uani d 1 . .
H H6A 0.3833(9) 0.4196(9) 0.4214(6) 0.046 Uiso d 1 . .
C C18 0.39799(6) 0.43829(7) 0.49600(4) 0.0363(2) Uani d 1 . .
C C19 0.51184(7) 0.37344(8) 0.52212(5) 0.0427(3) Uani d 1 . .
C C20 0.58383(9) 0.33716(11) 0.55080(6) 0.0620(4) Uani d 1 . .
H H20 0.599317 0.339769 0.586743 0.074 Uiso calc 1 . .
C C21 0.63136(10) 0.29722(12) 0.52407(7) 0.0707(5) Uani d 1 . .
H H21 0.679105 0.271436 0.542360 0.085 Uiso calc 1 . .
C C22 0.60934(9) 0.29471(11) 0.47023(7) 0.0655(4) Uani d 1 . .
H H22 0.643155 0.267777 0.453395 0.079 Uiso calc 1 . .
C C23 0.53885(8) 0.33102(10) 0.44121(6) 0.0533(3) Uani d 1 . .
H H23 0.524628 0.329751 0.405239 0.064 Uiso calc 1 . .
C C24 0.48992(6) 0.36969(8) 0.46827(5) 0.0392(3) Uani d 1 . .
C C25 0.32225(6) 0.48543(8) 0.49463(5) 0.0398(3) Uani d 1 . .
H H25A 0.306067 0.514498 0.462208 0.048 Uiso calc 1 . .
H H25B 0.334742 0.524315 0.522463 0.048 Uiso calc 1 . .
C C26 0.250000 0.43372(11) 0.500000 0.0390(3) Uani d 1 . .
H H26A 0.232262 0.399658 0.469816 0.047 Uiso calc 0.5 . .
H H26B 0.267739 0.399662 0.530185 0.047 Uiso calc 0.5 . .
C C27 0.24259(6) 0.48453(6) 0.66505(4) 0.0286(2) Uani d 1 . .
O O1 0.22012(4) 0.42873(5) 0.63255(3) 0.03592(18) Uani d 1 . .
O O2 0.19661(4) 0.51802(5) 0.68876(4) 0.0406(2) Uani d 1 . .
C C28 0.33088(5) 0.51107(6) 0.67702(4) 0.0279(2) Uani d 1 . .
C C29 0.36507(6) 0.55315(6) 0.72219(4) 0.0301(2) Uani d 1 . .
H H29 0.332142 0.568311 0.743553 0.036 Uiso calc 1 . .
C C30 0.44827(6) 0.57278(6) 0.73570(4) 0.0304(2) Uani d 1 . .
O O30 0.48495(5) 0.61169(5) 0.78071(4) 0.0434(2) Uani d 1 . .
H H30 0.4435(11) 0.6401(11) 0.7912(6) 0.065 Uiso d 1 . .
C C31 0.49785(6) 0.55062(6) 0.70354(4) 0.0305(2) Uani d 1 . .
O O31 0.57953(4) 0.56927(6) 0.71834(4) 0.0422(2) Uani d 1 . .
H H31 0.6076(11) 0.5401(10) 0.7008(7) 0.063 Uiso d 1 . .
C C32 0.46247(6) 0.51162(7) 0.65697(4) 0.0307(2) Uani d 1 . .
O O32 0.51369(5) 0.49489(6) 0.62700(3) 0.0442(2) Uani d 1 . .
H H32 0.4854(11) 0.4668(11) 0.5968(7) 0.066 Uiso d 1 . .
C C33 0.37932(6) 0.49074(7) 0.64409(4) 0.0307(2) Uani d 1 . .
H H33 0.356292 0.463270 0.613533 0.037 Uiso calc 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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -19 23 0.1472
7 -17 20 0.1344
22 -3 3 0.2578
21 10 -13 0.2800
6 19 -23 0.2319
1 19 -23 0.2162
-7 17 -20 0.2426
-19 9 -10 0.2770
-23 1 0 0.2954
-23 -5 7 0.3051
-5 -16 -23 0.1994
-22 -2 21 0.2512
20 -3 -27 0.3538
15 -18 -8 0.2158
-1 -24 -1 0.2024
7 23 -2 0.2016
-11 21 6 0.2865
-21 11 11 0.2911
10 20 -14 0.1820
-11 2 -28 0.2295
-8 -8 35 0.1914
-1 -7 35 0.2091
-2 6 -34 0.2770
-17 1 33 0.1983
1 9 33 0.2246
0 20 18 0.1842
-15 14 25 0.2473
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 C2 . . 104.86(10) ?
C1 N2 C7 . . 108.02(10) ?
C1 N2 H2 . . 120.2(9) ?
C7 N2 H2 . . 131.7(9) ?
C11 N3 C12 . . 109.02(10) ?
C11 N3 H3 . . 126.4(10) ?
C12 N3 H3 . . 124.5(10) ?
C11 N4 C17 . . 109.51(10) ?
C11 N4 H4 . . 122.3(11) ?
C17 N4 H4 . . 127.7(11) ?
N1 C1 N2 . . 112.50(11) ?
N1 C1 C8 . . 128.54(10) ?
N2 C1 C8 . . 118.96(11) ?
C3 C2 N1 . . 130.46(12) ?
C3 C2 C7 . . 119.99(12) ?
N1 C2 C7 . . 109.55(11) ?
C4 C3 C2 . . 117.62(15) ?
C4 C3 H3A . . 121.2 ?
C2 C3 H3A . . 121.2 ?
C3 C4 C5 . . 121.58(16) ?
C3 C4 H4A . . 119.2 ?
C5 C4 H4A . . 119.2 ?
C6 C5 C4 . . 121.89(14) ?
C6 C5 H5 . . 119.1 ?
C4 C5 H5 . . 119.1 ?
C5 C6 C7 . . 116.60(15) ?
C5 C6 H6 . . 121.7 ?
C7 C6 H6 . . 121.7 ?
N2 C7 C6 . . 132.60(13) ?
N2 C7 C2 . . 105.08(10) ?
C6 C7 C2 . . 122.32(13) ?
C1 C8 C9 . . 116.07(11) ?
C1 C8 H8A . . 108.3 ?
C9 C8 H8A . . 108.3 ?
C1 C8 H8B . . 108.3 ?
C9 C8 H8B . . 108.3 ?
H8A C8 H8B . . 107.4 ?
C8 C9 C10 . . 113.20(11) ?
C8 C9 H9A . . 108.9 ?
C10 C9 H9A . . 108.9 ?
C8 C9 H9B . . 108.9 ?
C10 C9 H9B . . 108.9 ?
H9A C9 H9B . . 107.8 ?
C11 C10 C9 . . 111.09(11) ?
C11 C10 H10A . . 109.4 ?
C9 C10 H10A . . 109.4 ?
C11 C10 H10B . . 109.4 ?
C9 C10 H10B . . 109.4 ?
H10A C10 H10B . . 108.0 ?
N3 C11 N4 . . 108.96(10) ?
N3 C11 C10 . . 126.19(11) ?
N4 C11 C10 . . 124.80(10) ?
N3 C12 C13 . . 131.16(12) ?
N3 C12 C17 . . 106.91(10) ?
C13 C12 C17 . . 121.92(12) ?
C14 C13 C12 . . 116.31(13) ?
C14 C13 H13 . . 121.8 ?
C12 C13 H13 . . 121.8 ?
C13 C14 C15 . . 121.82(13) ?
C13 C14 H14 . . 119.1 ?
C15 C14 H14 . . 119.1 ?
C16 C15 C14 . . 121.98(14) ?
C16 C15 H15 . . 119.0 ?
C14 C15 H15 . . 119.0 ?
C15 C16 C17 . . 116.41(13) ?
C15 C16 H16 . . 121.8 ?
C17 C16 H16 . . 121.8 ?
C16 C17 N4 . . 132.87(11) ?
C16 C17 C12 . . 121.54(11) ?
N4 C17 C12 . . 105.59(10) ?
C18 N5 C19 . . 105.11(10) ?
C18 N6 C24 . . 107.69(10) ?
C18 N6 H6A . . 121.8(9) ?
C24 N6 H6A . . 130.4(9) ?
N5 C18 N6 . . 112.55(10) ?
N5 C18 C25 . . 124.47(10) ?
N6 C18 C25 . . 122.98(10) ?
C20 C19 N5 . . 129.82(12) ?
C20 C19 C24 . . 120.47(12) ?
N5 C19 C24 . . 109.69(10) ?
C21 C20 C19 . . 117.68(13) ?
C21 C20 H20 . . 121.2 ?
C19 C20 H20 . . 121.2 ?
C20 C21 C22 . . 121.31(14) ?
C20 C21 H21 . . 119.3 ?
C22 C21 H21 . . 119.3 ?
C23 C22 C21 . . 121.81(14) ?
C23 C22 H22 . . 119.1 ?
C21 C22 H22 . . 119.1 ?
C22 C23 C24 . . 116.82(13) ?
C22 C23 H23 . . 121.6 ?
C24 C23 H23 . . 121.6 ?
N6 C24 C23 . . 133.16(11) ?
N6 C24 C19 . . 104.94(10) ?
C23 C24 C19 . . 121.89(11) ?
C18 C25 C26 . . 113.19(11) ?
C18 C25 H25A . . 108.9 ?
C26 C25 H25A . . 108.9 ?
C18 C25 H25B . . 108.9 ?
C26 C25 H25B . . 108.9 ?
H25A C25 H25B . . 107.8 ?
C25 C26 C25 2_556 . 111.10(14) ?
C25 C26 H26A 2_556 . 109.4 ?
C25 C26 H26A . . 109.4 ?
C25 C26 H26B 2_556 . 109.4 ?
C25 C26 H26B . . 109.4 ?
H26A C26 H26B . . 108.0 ?
O2 C27 O1 . . 124.43(9) ?
O2 C27 C28 . . 117.82(9) ?
O1 C27 C28 . . 117.73(9) ?
C29 C28 C33 . . 119.94(9) ?
C29 C28 C27 . . 119.76(9) ?
C33 C28 C27 . . 120.24(9) ?
C28 C29 C30 . . 120.36(9) ?
C28 C29 H29 . . 119.8 ?
C30 C29 H29 . . 119.8 ?
O30 C30 C29 . . 122.21(9) ?
O30 C30 C31 . . 117.75(8) ?
C29 C30 C31 . . 120.02(9) ?
C30 O30 H30 . . 107.7(11) ?
O31 C31 C32 . . 121.88(9) ?
O31 C31 C30 . . 118.67(9) ?
C32 C31 C30 . . 119.44(9) ?
C31 O31 H31 . . 110.8(11) ?
O32 C32 C33 . . 123.76(10) ?
O32 C32 C31 . . 116.02(9) ?
C33 C32 C31 . . 120.21(9) ?
C32 O32 H32 . . 110.7(11) ?
C28 C33 C32 . . 119.91(10) ?
C28 C33 H33 . . 120.0 ?
C32 C33 H33 . . 120.0 ?
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 . 1.3230(16) ?
N1 C2 . 1.3950(15) ?
N2 C1 . 1.3520(14) ?
N2 C7 . 1.3712(17) ?
N2 H2 . 0.936(16) ?
N3 C11 . 1.3282(14) ?
N3 C12 . 1.3831(15) ?
N3 H3 . 0.880(16) ?
N4 C11 . 1.3330(16) ?
N4 C17 . 1.3872(15) ?
N4 H4 . 0.867(16) ?
C1 C8 . 1.4841(18) ?
C2 C3 . 1.390(2) ?
C2 C7 . 1.4007(17) ?
C3 C4 . 1.382(2) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.392(3) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.371(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.3921(18) ?
C6 H6 . 0.9300 ?
C8 C9 . 1.5158(16) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.5298(19) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C11 . 1.4814(16) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C12 C13 . 1.3874(16) ?
C12 C17 . 1.3909(16) ?
C13 C14 . 1.371(2) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.397(2) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.375(2) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.3838(18) ?
C16 H16 . 0.9300 ?
N5 C18 . 1.3184(15) ?
N5 C19 . 1.3922(15) ?
N6 C18 . 1.3496(15) ?
N6 C24 . 1.3822(14) ?
N6 H6A . 0.893(15) ?
C18 C25 . 1.4910(15) ?
C19 C20 . 1.3920(18) ?
C19 C24 . 1.3933(17) ?
C20 C21 . 1.378(2) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.392(2) ?
C21 H21 . 0.9300 ?
C22 C23 . 1.377(2) ?
C22 H22 . 0.9300 ?
C23 C24 . 1.3909(17) ?
C23 H23 . 0.9300 ?
C25 C26 . 1.5293(15) ?
C25 H25A . 0.9700 ?
C25 H25B . 0.9700 ?
C26 H26A . 0.9700 ?
C26 H26B . 0.9700 ?
C27 O2 . 1.2545(12) ?
C27 O1 . 1.2648(13) ?
C27 C28 . 1.5024(13) ?
C28 C29 . 1.3876(14) ?
C28 C33 . 1.3910(14) ?
C29 C30 . 1.3903(13) ?
C29 H29 . 0.9300 ?
C30 O30 . 1.3665(13) ?
C30 C31 . 1.3973(14) ?
O30 H30 . 0.946(18) ?
C31 O31 . 1.3629(11) ?
C31 C32 . 1.3953(15) ?
O31 H31 . 0.894(18) ?
C32 O32 . 1.3521(12) ?
C32 C33 . 1.3946(13) ?
O32 H32 . 0.948(19) ?
C33 H33 . 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 H2 O2 6_665 0.936(16) 1.924(17) 2.8204(14) 159.7(13) yes
N3 H3 O1 . 0.880(16) 1.832(16) 2.6433(13) 152.4(14) yes
N4 H4 O30 4_546 0.867(16) 2.043(16) 2.8509(12) 154.6(14) yes
N4 H4 O31 4_546 0.867(16) 2.394(16) 3.0199(14) 129.5(13) yes
N6 H6A O1 2_556 0.893(15) 1.955(16) 2.8018(12) 157.9(13) yes
O30 H30 N1 4_556 0.946(18) 1.785(18) 2.7238(12) 171.3(16) yes
O31 H31 O2 6_665 0.894(18) 1.882(18) 2.7314(11) 157.8(16) yes
O32 H32 N5 . 0.948(19) 1.717(19) 2.6515(14) 167.9(16) yes
C8 H8A O32 . 0.97 2.52 3.4736(17) 167.9 no
C10 H10B N1 . 0.97 2.64 3.2566(16) 122.1 no
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
C2 N1 C1 N2 . . . . -0.44(14) ?
C2 N1 C1 C8 . . . . 179.31(12) ?
C7 N2 C1 N1 . . . . 0.51(14) ?
C7 N2 C1 C8 . . . . -179.26(11) ?
C1 N1 C2 C3 . . . . -179.18(15) ?
C1 N1 C2 C7 . . . . 0.21(14) ?
N1 C2 C3 C4 . . . . 179.44(15) ?
C7 C2 C3 C4 . . . . 0.1(2) ?
C2 C3 C4 C5 . . . . -0.3(3) ?
C3 C4 C5 C6 . . . . 0.3(3) ?
C4 C5 C6 C7 . . . . -0.2(3) ?
C1 N2 C7 C6 . . . . 179.15(14) ?
C1 N2 C7 C2 . . . . -0.35(13) ?
C5 C6 C7 N2 . . . . -179.35(15) ?
C5 C6 C7 C2 . . . . 0.1(2) ?
C3 C2 C7 N2 . . . . 179.55(13) ?
N1 C2 C7 N2 . . . . 0.09(14) ?
C3 C2 C7 C6 . . . . 0.0(2) ?
N1 C2 C7 C6 . . . . -179.47(12) ?
N1 C1 C8 C9 . . . . -9.7(2) ?
N2 C1 C8 C9 . . . . 170.03(11) ?
C1 C8 C9 C10 . . . . -63.93(16) ?
C8 C9 C10 C11 . . . . 179.45(11) ?
C12 N3 C11 N4 . . . . 0.14(15) ?
C12 N3 C11 C10 . . . . -177.42(13) ?
C17 N4 C11 N3 . . . . 0.16(16) ?
C17 N4 C11 C10 . . . . 177.76(13) ?
C9 C10 C11 N3 . . . . 103.86(15) ?
C9 C10 C11 N4 . . . . -73.33(17) ?
C11 N3 C12 C13 . . . . -179.73(15) ?
C11 N3 C12 C17 . . . . -0.38(15) ?
N3 C12 C13 C14 . . . . 177.75(15) ?
C17 C12 C13 C14 . . . . -1.5(2) ?
C12 C13 C14 C15 . . . . 1.5(3) ?
C13 C14 C15 C16 . . . . -0.3(3) ?
C14 C15 C16 C17 . . . . -0.9(3) ?
C15 C16 C17 N4 . . . . -178.51(16) ?
C15 C16 C17 C12 . . . . 0.9(2) ?
C11 N4 C17 C16 . . . . 179.11(16) ?
C11 N4 C17 C12 . . . . -0.39(15) ?
N3 C12 C17 C16 . . . . -179.11(13) ?
C13 C12 C17 C16 . . . . 0.3(2) ?
N3 C12 C17 N4 . . . . 0.46(15) ?
C13 C12 C17 N4 . . . . 179.89(13) ?
C19 N5 C18 N6 . . . . -0.52(15) ?
C19 N5 C18 C25 . . . . 178.77(11) ?
C24 N6 C18 N5 . . . . -0.21(14) ?
C24 N6 C18 C25 . . . . -179.51(11) ?
C18 N5 C19 C20 . . . . 179.82(16) ?
C18 N5 C19 C24 . . . . 1.06(15) ?
N5 C19 C20 C21 . . . . -179.31(16) ?
C24 C19 C20 C21 . . . . -0.7(2) ?
C19 C20 C21 C22 . . . . 1.5(3) ?
C20 C21 C22 C23 . . . . -0.8(3) ?
C21 C22 C23 C24 . . . . -0.7(3) ?
C18 N6 C24 C23 . . . . -178.24(15) ?
C18 N6 C24 C19 . . . . 0.84(14) ?
C22 C23 C24 N6 . . . . -179.50(15) ?
C22 C23 C24 C19 . . . . 1.5(2) ?
C20 C19 C24 N6 . . . . 179.93(14) ?
N5 C19 C24 N6 . . . . -1.18(15) ?
C20 C19 C24 C23 . . . . -0.9(2) ?
N5 C19 C24 C23 . . . . 178.03(13) ?
N5 C18 C25 C26 . . . . -86.02(14) ?
N6 C18 C25 C26 . . . . 93.19(13) ?
C18 C25 C26 C25 . . . 2_556 172.70(12) ?
O2 C27 C28 C29 . . . . 18.00(15) ?
O1 C27 C28 C29 . . . . -160.52(10) ?
O2 C27 C28 C33 . . . . -164.68(10) ?
O1 C27 C28 C33 . . . . 16.80(15) ?
C33 C28 C29 C30 . . . . -2.24(16) ?
C27 C28 C29 C30 . . . . 175.09(9) ?
C28 C29 C30 O30 . . . . -177.66(10) ?
C28 C29 C30 C31 . . . . 0.45(16) ?
O30 C30 C31 O31 . . . . -0.48(16) ?
C29 C30 C31 O31 . . . . -178.67(10) ?
O30 C30 C31 C32 . . . . -179.25(10) ?
C29 C30 C31 C32 . . . . 2.55(16) ?
O31 C31 C32 O32 . . . . -1.24(16) ?
C30 C31 C32 O32 . . . . 177.49(10) ?
O31 C31 C32 C33 . . . . 177.48(10) ?
C30 C31 C32 C33 . . . . -3.78(16) ?
C29 C28 C33 C32 . . . . 1.01(16) ?
C27 C28 C33 C32 . . . . -176.32(9) ?
O32 C32 C33 C28 . . . . -179.36(10) ?
C31 C32 C33 C28 . . . . 2.02(16) ?
