#------------------------------------------------------------------------------
#$Date: 2024-10-01 05:14:26 +0300 (Tue, 01 Oct 2024) $
#$Revision: 294950 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/32/2023263.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_2023263
loop_
_publ_author_name
'Uppu, Rao M.'
'Chikkula, Krishnaveni'
'Saneei, Soheil'
'Babu, Sainath'
'Fronczek, Frank R.'
_publ_section_title
;
 Structure of 2,3,5-triphenyltetrazol-3-ium chloride hemipentahydrate
;
_journal_coeditor_code           HB8107
_journal_issue                   10
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_page_first              1097
_journal_page_last               1100
_journal_paper_doi               10.1107/S205698902400940X
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C19 H15 N4 +, Cl -, 2.5H2 O'
_chemical_formula_moiety         'C19 H15 N4 +, Cl -, 2.5(H2 O)'
_chemical_formula_sum            'C19 H20 Cl N4 O2.5'
_chemical_formula_weight         379.84
_chemical_name_systematic
;
2,3,5-Triphenyltetrazol-3-ium chloride hemipentahydrate
;
_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
_audit_creation_method           SHELXL-2019/1
_cell_angle_alpha                94.808(2)
_cell_angle_beta                 104.562(2)
_cell_angle_gamma                95.408(2)
_cell_formula_units_Z            4
_cell_length_a                   9.5599(4)
_cell_length_b                   11.8056(5)
_cell_length_c                   17.5322(7)
_cell_measurement_reflns_used    9994
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      26.33
_cell_measurement_theta_min      2.62
_cell_volume                     1894.70(14)
_computing_cell_refinement
;
SAINT (Bruker, 2022)
;
_computing_data_collection
;
APEX4 (Bruker, 2022)
;
_computing_data_reduction
;
SAINT (Bruker, 2022)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2020)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2019/1 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018/2 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100.0(5)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture DUO with Photon III C14'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_source         'I\mS 3.0 microfocus'
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56086
_diffrn_reflns_av_R_equivalents  0.0835
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            125520
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         26.428
_diffrn_reflns_theta_min         2.092
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       fragment
_exptl_crystal_F_000             796
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.628
_refine_diff_density_min         -0.666
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     508
_refine_ls_number_reflns         15816
_refine_ls_number_restraints     45
_refine_ls_restrained_S_all      1.157
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0632
_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)+(0.0502P)²+1.0730P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1340
_refine_ls_wR_factor_ref         0.1413
_reflns_number_gt                13259
_reflns_number_total             15816
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb8107.cif
_cod_data_source_block           I
_cod_original_formula_sum        'C19 H20 Cl N4 O2.50'
_cod_database_code               2023263
_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   0.961
_shelx_estimated_absorpt_t_max   0.970
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
Cl Cl1 0.70828(4) 0.44966(3) 0.10654(2) 0.02287(8) Uani d 1 . .
Cl Cl2 0.36722(5) 0.81273(4) 0.47669(2) 0.03148(10) Uani d 1 . .
N N1 1.06087(12) 0.41493(9) 0.30022(7) 0.01281(18) Uani d 1 . .
N N2 1.01796(12) 0.51703(9) 0.29532(6) 0.01148(18) Uani d 1 . .
N N3 0.91361(12) 0.52776(9) 0.33271(6) 0.01127(18) Uani d 1 . .
N N4 0.88812(12) 0.43342(9) 0.36428(7) 0.01265(18) Uani d 1 . .
C C1 0.98037(13) 0.36431(10) 0.34357(7) 0.0119(2) Uani d 1 . .
C C2 0.99419(14) 0.24860(10) 0.36518(7) 0.0127(2) Uani d 1 . .
C C3 1.11278(15) 0.19497(12) 0.35379(8) 0.0168(2) Uani d 1 . .
H H3 1.184221 0.234181 0.333244 0.020 Uiso calc 1 . .
C C4 1.12526(17) 0.08350(12) 0.37282(9) 0.0207(3) Uani d 1 . .
H H4 1.206066 0.046687 0.365849 0.025 Uiso calc 1 . .
C C5 1.01958(19) 0.02616(12) 0.40200(9) 0.0226(3) Uani d 1 . .
H H5 1.027171 -0.050537 0.413628 0.027 Uiso calc 1 . .
C C6 0.90284(18) 0.08019(12) 0.41429(8) 0.0204(3) Uani d 1 . .
H H6 0.831886 0.040812 0.435081 0.025 Uiso calc 1 . .
C C7 0.88968(15) 0.19187(11) 0.39619(8) 0.0154(2) Uani d 1 . .
H H7 0.810327 0.229196 0.404859 0.019 Uiso calc 1 . .
C C8 1.08402(13) 0.60275(10) 0.25710(7) 0.0118(2) Uani d 1 . .
C C9 1.10553(15) 0.56581(12) 0.18416(8) 0.0153(2) Uani d 1 . .
H H9 1.070334 0.490211 0.159463 0.018 Uiso calc 1 . .
C C10 1.18016(16) 0.64285(13) 0.14837(8) 0.0186(2) Uani d 1 . .
H H10 1.197734 0.619924 0.098701 0.022 Uiso calc 1 . .
C C11 1.22917(15) 0.75340(13) 0.18512(9) 0.0195(3) Uani d 1 . .
H H11 1.279070 0.806102 0.160079 0.023 Uiso calc 1 . .
C C12 1.20566(15) 0.78746(12) 0.25834(9) 0.0177(2) Uani d 1 . .
H H12 1.239657 0.863305 0.282850 0.021 Uiso calc 1 . .
C C13 1.13283(14) 0.71156(11) 0.29605(8) 0.0145(2) Uani d 1 . .
H H13 1.117314 0.733548 0.346380 0.017 Uiso calc 1 . .
C C14 0.83772(14) 0.62624(10) 0.33853(7) 0.0122(2) Uani d 1 . .
C C15 0.77717(15) 0.67406(12) 0.27005(8) 0.0160(2) Uani d 1 . .
H H15 0.786806 0.643983 0.219891 0.019 Uiso calc 1 . .
C C16 0.70196(16) 0.76752(13) 0.27755(9) 0.0210(3) Uani d 1 . .
H H16 0.661365 0.803899 0.232134 0.025 Uiso calc 1 . .
C C17 0.68564(17) 0.80833(13) 0.35140(10) 0.0233(3) Uani d 1 . .
H H17 0.632602 0.871611 0.355801 0.028 Uiso calc 1 . .
C C18 0.74620(18) 0.75730(13) 0.41848(9) 0.0228(3) Uani d 1 . .
H H18 0.733652 0.785380 0.468421 0.027 Uiso calc 1 . .
C C19 0.82497(16) 0.66550(12) 0.41304(8) 0.0176(2) Uani d 1 . .
H H19 0.868633 0.630747 0.458692 0.021 Uiso calc 1 . .
N N5 0.34121(12) 0.77429(9) 0.78463(6) 0.01196(18) Uani d 1 . .
N N6 0.45974(12) 0.72436(9) 0.79383(6) 0.01103(17) Uani d 1 . .
N N7 0.54655(11) 0.75476(9) 0.86647(6) 0.01081(17) Uani d 1 . .
N N8 0.48642(12) 0.82506(9) 0.90686(6) 0.01171(18) Uani d 1 . .
C C20 0.35971(13) 0.83685(10) 0.85526(7) 0.01125(19) Uani d 1 . .
C C21 0.25809(14) 0.91367(11) 0.87263(7) 0.0126(2) Uani d 1 . .
C C22 0.16689(15) 0.95904(12) 0.81057(8) 0.0167(2) Uani d 1 . .
H H22 0.168326 0.937903 0.757308 0.020 Uiso calc 1 . .
C C23 0.07367(18) 1.03559(13) 0.82727(10) 0.0233(3) Uani d 1 . .
H H23 0.011239 1.067061 0.785300 0.028 Uiso calc 1 . .
C C24 0.07175(18) 1.06608(14) 0.90525(10) 0.0257(3) Uani d 1 . .
H H24 0.007532 1.117997 0.916441 0.031 Uiso calc 1 . .
C C25 0.16344(17) 1.02088(13) 0.96690(9) 0.0214(3) Uani d 1 . .
H H25 0.161744 1.042165 1.020099 0.026 Uiso calc 1 . .
C C26 0.25762(15) 0.94473(12) 0.95119(8) 0.0164(2) Uani d 1 . .
H H26 0.320861 0.914190 0.993332 0.020 Uiso calc 1 . .
C C27 0.49263(13) 0.64728(11) 0.73433(7) 0.0121(2) Uani d 1 . .
C C28 0.52080(14) 0.53771(11) 0.75180(8) 0.0153(2) Uani d 1 . .
H H28 0.517685 0.512997 0.801599 0.018 Uiso calc 1 . .
C C29 0.55378(15) 0.46552(13) 0.69343(9) 0.0200(3) Uani d 1 . .
H H29 0.573212 0.389835 0.703092 0.024 Uiso calc 1 . .
C C30 0.55841(16) 0.50361(15) 0.62116(9) 0.0237(3) Uani d 1 . .
H H30 0.582347 0.454021 0.582032 0.028 Uiso calc 1 . .
C C31 0.52840(17) 0.61350(15) 0.60550(8) 0.0224(3) Uani d 1 . .
H H31 0.530920 0.638198 0.555610 0.027 Uiso calc 1 . .
C C32 0.49462(15) 0.68766(13) 0.66259(8) 0.0169(2) Uani d 1 . .
H H32 0.473763 0.762990 0.652720 0.020 Uiso calc 1 . .
C C33 0.69328(13) 0.72747(11) 0.89345(7) 0.01130(19) Uani d 1 . .
C C34 0.79458(14) 0.76919(12) 0.85529(8) 0.0147(2) Uani d 1 . .
H H34 0.767638 0.812168 0.811542 0.018 Uiso calc 1 . .
C C35 0.93677(14) 0.74586(13) 0.88334(8) 0.0176(2) Uani d 1 . .
H H35 1.008994 0.772656 0.858364 0.021 Uiso calc 1 . .
C C36 0.97440(15) 0.68333(13) 0.94797(8) 0.0184(2) Uani d 1 . .
H H36 1.072249 0.668184 0.966914 0.022 Uiso calc 1 . .
C C37 0.86978(15) 0.64294(13) 0.98493(8) 0.0181(2) Uani d 1 . .
H H37 0.896309 0.600303 1.028887 0.022 Uiso calc 1 . .
C C38 0.72645(14) 0.66494(12) 0.95758(8) 0.0149(2) Uani d 1 . .
H H38 0.653676 0.637922 0.982119 0.018 Uiso calc 1 . .
O O1 0.83271(13) 0.41876(10) 0.53365(6) 0.0209(2) Uani d 1 . .
H H1W 0.780(2) 0.3554(14) 0.5308(14) 0.031 Uiso d 1 . .
H H2W 0.828(3) 0.430(2) 0.4856(9) 0.031 Uiso d 1 . .
O O2 0.53149(13) 0.99355(10) 0.61966(6) 0.0212(2) Uani d 1 . .
H H3W 0.484(2) 0.9458(17) 0.5819(11) 0.032 Uiso d 1 . .
H H4W 0.558(3) 1.0481(16) 0.5968(13) 0.032 Uiso d 1 . .
O O3 0.57974(15) 0.96751(10) 0.78259(7) 0.0254(2) Uani d 1 . .
H H5W 0.564(3) 0.980(2) 0.7343(9) 0.038 Uiso d 1 . .
H H6W 0.556(3) 1.0222(17) 0.8094(13) 0.038 Uiso d 1 . .
O O4 0.46846(15) 0.62378(11) 0.07228(8) 0.0277(2) Uani d 1 . .
H H7W 0.420(3) 0.605(2) 0.0242(9) 0.041 Uiso d 1 . .
H H8W 0.533(2) 0.5782(19) 0.0806(15) 0.041 Uiso d 1 . .
O O5 0.49505(13) 1.14221(10) 0.89204(7) 0.0219(2) Uani d 1 . .
H H9W 0.502(3) 1.2147(12) 0.9044(14) 0.033 Uiso d 1 . .
H H10W 0.435(2) 1.1154(19) 0.9169(13) 0.033 Uiso 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 0.0015 0.0009 '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'
Cl Cl 0.0998 0.0984 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 '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
N2 N1 C1 . . 103.93(10) ?
N1 N2 N3 . . 110.20(10) ?
N1 N2 C8 . . 122.11(10) ?
N3 N2 C8 . . 127.63(10) ?
N4 N3 N2 . . 109.93(10) ?
N4 N3 C14 . . 123.73(10) ?
N2 N3 C14 . . 126.34(10) ?
N3 N4 C1 . . 103.88(10) ?
N1 C1 N4 . . 112.03(11) ?
N1 C1 C2 . . 122.91(11) ?
N4 C1 C2 . . 125.05(11) ?
C7 C2 C3 . . 120.57(12) ?
C7 C2 C1 . . 120.39(11) ?
C3 C2 C1 . . 119.04(12) ?
C4 C3 C2 . . 119.40(13) ?
C4 C3 H3 . . 120.3 ?
C2 C3 H3 . . 120.3 ?
C5 C4 C3 . . 120.02(13) ?
C5 C4 H4 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
C4 C5 C6 . . 120.46(13) ?
C4 C5 H5 . . 119.8 ?
C6 C5 H5 . . 119.8 ?
C5 C6 C7 . . 120.12(14) ?
C5 C6 H6 . . 119.9 ?
C7 C6 H6 . . 119.9 ?
C6 C7 C2 . . 119.40(13) ?
C6 C7 H7 . . 120.3 ?
C2 C7 H7 . . 120.3 ?
C13 C8 C9 . . 123.75(12) ?
C13 C8 N2 . . 120.11(11) ?
C9 C8 N2 . . 115.91(11) ?
C8 C9 C10 . . 117.88(12) ?
C8 C9 H9 . . 121.1 ?
C10 C9 H9 . . 121.1 ?
C9 C10 C11 . . 120.09(13) ?
C9 C10 H10 . . 120.0 ?
C11 C10 H10 . . 120.0 ?
C10 C11 C12 . . 120.44(13) ?
C10 C11 H11 . . 119.8 ?
C12 C11 H11 . . 119.8 ?
C11 C12 C13 . . 120.70(13) ?
C11 C12 H12 . . 119.7 ?
C13 C12 H12 . . 119.7 ?
C8 C13 C12 . . 117.14(12) ?
C8 C13 H13 . . 121.4 ?
C12 C13 H13 . . 121.4 ?
C15 C14 C19 . . 123.67(12) ?
C15 C14 N3 . . 118.95(11) ?
C19 C14 N3 . . 117.34(11) ?
C14 C15 C16 . . 117.46(13) ?
C14 C15 H15 . . 121.3 ?
C16 C15 H15 . . 121.3 ?
C15 C16 C17 . . 120.35(14) ?
C15 C16 H16 . . 119.8 ?
C17 C16 H16 . . 119.8 ?
C18 C17 C16 . . 120.54(13) ?
C18 C17 H17 . . 119.7 ?
C16 C17 H17 . . 119.7 ?
C19 C18 C17 . . 120.35(14) ?
C19 C18 H18 . . 119.8 ?
C17 C18 H18 . . 119.8 ?
C18 C19 C14 . . 117.61(13) ?
C18 C19 H19 . . 121.2 ?
C14 C19 H19 . . 121.2 ?
N6 N5 C20 . . 103.54(10) ?
N5 N6 N7 . . 110.29(10) ?
N5 N6 C27 . . 125.17(10) ?
N7 N6 C27 . . 124.54(10) ?
N8 N7 N6 . . 110.23(10) ?
N8 N7 C33 . . 124.23(10) ?
N6 N7 C33 . . 125.03(10) ?
N7 N8 C20 . . 103.56(10) ?
N8 C20 N5 . . 112.38(11) ?
N8 C20 C21 . . 123.45(11) ?
N5 C20 C21 . . 124.09(11) ?
C22 C21 C26 . . 120.79(12) ?
C22 C21 C20 . . 119.33(11) ?
C26 C21 C20 . . 119.83(12) ?
C23 C22 C21 . . 119.41(13) ?
C23 C22 H22 . . 120.3 ?
C21 C22 H22 . . 120.3 ?
C24 C23 C22 . . 120.09(15) ?
C24 C23 H23 . . 120.0 ?
C22 C23 H23 . . 120.0 ?
C25 C24 C23 . . 120.21(14) ?
C25 C24 H24 . . 119.9 ?
C23 C24 H24 . . 119.9 ?
C24 C25 C26 . . 120.37(13) ?
C24 C25 H25 . . 119.8 ?
C26 C25 H25 . . 119.8 ?
C25 C26 C21 . . 119.12(13) ?
C25 C26 H26 . . 120.4 ?
C21 C26 H26 . . 120.4 ?
C32 C27 C28 . . 123.81(12) ?
C32 C27 N6 . . 117.50(12) ?
C28 C27 N6 . . 118.68(11) ?
C27 C28 C29 . . 117.38(13) ?
C27 C28 H28 . . 121.3 ?
C29 C28 H28 . . 121.3 ?
C30 C29 C28 . . 120.35(14) ?
C30 C29 H29 . . 119.8 ?
C28 C29 H29 . . 119.8 ?
C29 C30 C31 . . 120.68(13) ?
C29 C30 H30 . . 119.7 ?
C31 C30 H30 . . 119.7 ?
C30 C31 C32 . . 120.33(14) ?
C30 C31 H31 . . 119.8 ?
C32 C31 H31 . . 119.8 ?
C27 C32 C31 . . 117.43(14) ?
C27 C32 H32 . . 121.3 ?
C31 C32 H32 . . 121.3 ?
C38 C33 C34 . . 123.74(12) ?
C38 C33 N7 . . 118.40(11) ?
C34 C33 N7 . . 117.82(11) ?
C33 C34 C35 . . 117.50(12) ?
C33 C34 H34 . . 121.3 ?
C35 C34 H34 . . 121.3 ?
C34 C35 C36 . . 120.40(12) ?
C34 C35 H35 . . 119.8 ?
C36 C35 H35 . . 119.8 ?
C37 C36 C35 . . 120.51(13) ?
C37 C36 H36 . . 119.7 ?
C35 C36 H36 . . 119.7 ?
C38 C37 C36 . . 120.04(13) ?
C38 C37 H37 . . 120.0 ?
C36 C37 H37 . . 120.0 ?
C33 C38 C37 . . 117.80(12) ?
C33 C38 H38 . . 121.1 ?
C37 C38 H38 . . 121.1 ?
H1W O1 H2W . . 105(2) ?
H3W O2 H4W . . 103(2) ?
H5W O3 H6W . . 110(2) ?
H7W O4 H8W . . 105(2) ?
H9W O5 H10W . . 103(2) ?
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 N2 . 1.3120(15) ?
N1 C1 . 1.3455(16) ?
N2 N3 . 1.3341(14) ?
N2 C8 . 1.4415(16) ?
N3 N4 . 1.3137(15) ?
N3 C14 . 1.4370(16) ?
N4 C1 . 1.3500(16) ?
C1 C2 . 1.4569(17) ?
C2 C7 . 1.3966(18) ?
C2 C3 . 1.3979(18) ?
C3 C4 . 1.393(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.389(2) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.390(2) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.3914(19) ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
C8 C13 . 1.3835(17) ?
C8 C9 . 1.3870(18) ?
C9 C10 . 1.3886(19) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.389(2) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.391(2) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.3922(19) ?
C12 H12 . 0.9500 ?
C13 H13 . 0.9500 ?
C14 C15 . 1.3859(18) ?
C14 C19 . 1.3877(18) ?
C15 C16 . 1.387(2) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.394(2) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.387(2) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.387(2) ?
C18 H18 . 0.9500 ?
C19 H19 . 0.9500 ?
N5 N6 . 1.3066(15) ?
N5 C20 . 1.3498(16) ?
N6 N7 . 1.3324(14) ?
N6 C27 . 1.4404(16) ?
N7 N8 . 1.3103(14) ?
N7 C33 . 1.4395(16) ?
N8 C20 . 1.3442(16) ?
C20 C21 . 1.4586(17) ?
C21 C22 . 1.3927(19) ?
C21 C26 . 1.3965(18) ?
C22 C23 . 1.391(2) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.389(2) ?
C23 H23 . 0.9500 ?
C24 C25 . 1.389(2) ?
C24 H24 . 0.9500 ?
C25 C26 . 1.389(2) ?
C25 H25 . 0.9500 ?
C26 H26 . 0.9500 ?
C27 C32 . 1.3858(18) ?
C27 C28 . 1.3893(19) ?
C28 C29 . 1.3927(19) ?
C28 H28 . 0.9500 ?
C29 C30 . 1.389(2) ?
C29 H29 . 0.9500 ?
C30 C31 . 1.390(2) ?
C30 H30 . 0.9500 ?
C31 C32 . 1.3934(19) ?
C31 H31 . 0.9500 ?
C32 H32 . 0.9500 ?
C33 C38 . 1.3834(18) ?
C33 C34 . 1.3854(17) ?
C34 C35 . 1.3866(19) ?
C34 H34 . 0.9500 ?
C35 C36 . 1.394(2) ?
C35 H35 . 0.9500 ?
C36 C37 . 1.391(2) ?
C36 H36 . 0.9500 ?
C37 C38 . 1.3902(19) ?
C37 H37 . 0.9500 ?
C38 H38 . 0.9500 ?
O1 H1W . 0.851(14) ?
O1 H2W . 0.853(14) ?
O2 H3W . 0.836(14) ?
O2 H4W . 0.838(14) ?
O3 H5W . 0.849(14) ?
O3 H6W . 0.849(14) ?
O4 H7W . 0.852(14) ?
O4 H8W . 0.849(14) ?
O5 H9W . 0.857(14) ?
O5 H10W . 0.854(14) ?
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
O1 H1W Cl2 2_666 0.851(14) 2.298(14) 3.1483(12) 178(2) yes
O1 H2W N4 . 0.853(14) 2.344(15) 3.1605(15) 160(2) yes
O2 H3W Cl2 . 0.836(14) 2.295(14) 3.1302(12) 176(2) yes
O2 H4W Cl2 2_676 0.838(14) 2.339(14) 3.1740(12) 175(2) yes
O3 H5W O2 . 0.849(14) 1.978(14) 2.8246(16) 175(2) yes
O3 H6W O5 . 0.849(14) 2.164(15) 3.0040(17) 171(2) yes
O4 H7W Cl1 2_665 0.852(14) 2.317(15) 3.1687(14) 179(3) yes
O4 H8W Cl1 . 0.849(14) 2.352(15) 3.2008(14) 178(2) yes
O5 H9W O4 2_676 0.857(14) 1.896(14) 2.7503(17) 175(2) yes
O5 H10W Cg6 . 0.854(14) 2.76(2) 3.4646(14) 140.8(18) yes
C4 H4 O2 2_766 0.95 2.55 3.461(2) 160 yes
C11 H11 O5 2_776 0.95 2.59 3.429(2) 147 yes
C15 H15 Cl1 . 0.95 2.82 3.6219(14) 143 yes
C16 H16 O5 2_676 0.95 2.48 3.4084(19) 165 yes
C17 H17 O2 2_676 0.95 2.42 3.359(2) 168 yes
C26 H26 O5 2_677 0.95 2.50 3.4440(19) 173 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
C1 N1 N2 N3 . . . . -1.18(13) ?
C1 N1 N2 C8 . . . . 176.26(11) ?
N1 N2 N3 N4 . . . . 1.26(14) ?
C8 N2 N3 N4 . . . . -175.99(11) ?
N1 N2 N3 C14 . . . . -178.51(11) ?
C8 N2 N3 C14 . . . . 4.2(2) ?
N2 N3 N4 C1 . . . . -0.74(13) ?
C14 N3 N4 C1 . . . . 179.04(11) ?
N2 N1 C1 N4 . . . . 0.73(14) ?
N2 N1 C1 C2 . . . . -178.88(11) ?
N3 N4 C1 N1 . . . . 0.00(14) ?
N3 N4 C1 C2 . . . . 179.60(12) ?
N1 C1 C2 C7 . . . . -167.19(12) ?
N4 C1 C2 C7 . . . . 13.25(19) ?
N1 C1 C2 C3 . . . . 12.26(19) ?
N4 C1 C2 C3 . . . . -167.30(13) ?
C7 C2 C3 C4 . . . . 0.7(2) ?
C1 C2 C3 C4 . . . . -178.73(12) ?
C2 C3 C4 C5 . . . . 0.7(2) ?
C3 C4 C5 C6 . . . . -1.6(2) ?
C4 C5 C6 C7 . . . . 1.0(2) ?
C5 C6 C7 C2 . . . . 0.4(2) ?
C3 C2 C7 C6 . . . . -1.3(2) ?
C1 C2 C7 C6 . . . . 178.16(12) ?
N1 N2 C8 C13 . . . . -128.71(13) ?
N3 N2 C8 C13 . . . . 48.25(18) ?
N1 N2 C8 C9 . . . . 45.93(17) ?
N3 N2 C8 C9 . . . . -137.11(13) ?
C13 C8 C9 C10 . . . . -0.1(2) ?
N2 C8 C9 C10 . . . . -174.54(12) ?
C8 C9 C10 C11 . . . . -0.8(2) ?
C9 C10 C11 C12 . . . . 0.8(2) ?
C10 C11 C12 C13 . . . . 0.0(2) ?
C9 C8 C13 C12 . . . . 0.9(2) ?
N2 C8 C13 C12 . . . . 175.12(12) ?
C11 C12 C13 C8 . . . . -0.9(2) ?
N4 N3 C14 C15 . . . . -129.44(13) ?
N2 N3 C14 C15 . . . . 50.30(18) ?
N4 N3 C14 C19 . . . . 48.26(17) ?
N2 N3 C14 C19 . . . . -132.00(13) ?
C19 C14 C15 C16 . . . . 1.1(2) ?
N3 C14 C15 C16 . . . . 178.63(12) ?
C14 C15 C16 C17 . . . . -1.8(2) ?
C15 C16 C17 C18 . . . . 1.0(2) ?
C16 C17 C18 C19 . . . . 0.6(2) ?
C17 C18 C19 C14 . . . . -1.3(2) ?
C15 C14 C19 C18 . . . . 0.4(2) ?
N3 C14 C19 C18 . . . . -177.15(13) ?
C20 N5 N6 N7 . . . . 0.02(13) ?
C20 N5 N6 C27 . . . . 179.94(11) ?
N5 N6 N7 N8 . . . . 0.34(14) ?
C27 N6 N7 N8 . . . . -179.58(11) ?
N5 N6 N7 C33 . . . . -171.74(11) ?
C27 N6 N7 C33 . . . . 8.34(18) ?
N6 N7 N8 C20 . . . . -0.53(13) ?
C33 N7 N8 C20 . . . . 171.62(11) ?
N7 N8 C20 N5 . . . . 0.56(14) ?
N7 N8 C20 C21 . . . . -176.25(11) ?
N6 N5 C20 N8 . . . . -0.37(14) ?
N6 N5 C20 C21 . . . . 176.42(11) ?
N8 C20 C21 C22 . . . . 152.30(13) ?
N5 C20 C21 C22 . . . . -24.14(19) ?
N8 C20 C21 C26 . . . . -24.95(19) ?
N5 C20 C21 C26 . . . . 158.61(12) ?
C26 C21 C22 C23 . . . . -0.4(2) ?
C20 C21 C22 C23 . . . . -177.66(13) ?
C21 C22 C23 C24 . . . . -0.1(2) ?
C22 C23 C24 C25 . . . . 0.4(3) ?
C23 C24 C25 C26 . . . . -0.1(2) ?
C24 C25 C26 C21 . . . . -0.4(2) ?
C22 C21 C26 C25 . . . . 0.7(2) ?
C20 C21 C26 C25 . . . . 177.93(12) ?
N5 N6 C27 C32 . . . . 57.53(17) ?
N7 N6 C27 C32 . . . . -122.57(13) ?
N5 N6 C27 C28 . . . . -122.66(14) ?
N7 N6 C27 C28 . . . . 57.24(17) ?
C32 C27 C28 C29 . . . . 0.5(2) ?
N6 C27 C28 C29 . . . . -179.33(12) ?
C27 C28 C29 C30 . . . . 0.3(2) ?
C28 C29 C30 C31 . . . . -0.9(2) ?
C29 C30 C31 C32 . . . . 0.7(2) ?
C28 C27 C32 C31 . . . . -0.6(2) ?
N6 C27 C32 C31 . . . . 179.15(12) ?
C30 C31 C32 C27 . . . . 0.1(2) ?
N8 N7 C33 C38 . . . . 68.04(16) ?
N6 N7 C33 C38 . . . . -120.96(13) ?
N8 N7 C33 C34 . . . . -109.63(14) ?
N6 N7 C33 C34 . . . . 61.37(17) ?
C38 C33 C34 C35 . . . . 0.3(2) ?
N7 C33 C34 C35 . . . . 177.85(11) ?
C33 C34 C35 C36 . . . . -0.5(2) ?
C34 C35 C36 C37 . . . . 0.4(2) ?
C35 C36 C37 C38 . . . . -0.1(2) ?
C34 C33 C38 C37 . . . . -0.1(2) ?
N7 C33 C38 C37 . . . . -177.58(12) ?
C36 C37 C38 C33 . . . . -0.1(2) ?
