#------------------------------------------------------------------------------
#$Date: 2023-05-23 10:43:49 +0300 (Tue, 23 May 2023) $
#$Revision: 283953 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/72/8107247.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_8107247
loop_
_publ_author_name
'Zhan, An'
'Liu, E.'
'Jian, Fangfang'
'Liang, Tongling'
_publ_section_title
;
 The crystal structure of
 N′,N″,2-tris((E)-5-chloro-2-hydroxybenzylidene)hydrazine-1-carbohydrazonhydrazide
 hydrochloride -- methanol (1/3), C25H30Cl4N6O6
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              903
_journal_page_last               905
_journal_paper_doi               10.1515/ncrs-2022-0308
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C22 H18 Cl3 N6 O3, Cl, 3(C H4 O)'
_chemical_formula_sum            'C25 H30 Cl4 N6 O6'
_chemical_formula_weight         652.35
_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   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                106.929(2)
_cell_angle_beta                 99.753(2)
_cell_angle_gamma                98.675(2)
_cell_formula_units_Z            2
_cell_length_a                   9.2652(2)
_cell_length_b                   11.7642(3)
_cell_length_c                   14.6692(4)
_cell_measurement_reflns_used    14961
_cell_measurement_temperature    170.01(11)
_cell_measurement_theta_max      76.9750
_cell_measurement_theta_min      3.1940
_cell_volume                     1473.15(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.01(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     26.00 110.00   0.50    0.08    --   47.70  74.00 -10.00  168
  2  ω     89.00 178.00   0.50    0.10    --  107.36  74.00 -10.00  178
  3  ω     94.00 175.00   0.50    0.10    --  107.36  57.00 -60.00  162
  4  ω     94.00 177.00   0.50    0.10    --  107.36  38.00 -90.00  166
  5  ω     24.00  78.00   0.50    0.08    --   47.70-125.00  90.00  108
  6  ω     24.00  62.00   0.50    0.08    --   47.70-125.00 -90.00   76
  7  ω     69.00  94.00   0.50    0.08    --   47.70-125.00 -90.00   50
  8  ω     39.00  67.00   0.50    0.08    --   47.70 -74.00-138.00   56
  9  ω    -19.00  25.00   0.50    0.08    --   47.70 -74.00-138.00   88
 10  ω    -16.00  42.00   0.50    0.08    --   47.70 -38.00-120.00  116
 11  ω     79.00 111.00   0.50    0.10    --  107.36-125.00 -30.00   64
 12  ω     36.00  90.00   0.50    0.10    --  107.36 -99.00  60.00  108
 13  ω     45.00  75.00   0.50    0.10    --  107.36-125.00 -30.00   60
 14  ω     35.00 106.00   0.50    0.10    --  107.36 -99.00 150.00  142
 15  ω     69.00 106.00   0.50    0.10    --  107.36 -99.00 -30.00   74
 16  ω     49.00 105.00   0.50    0.10    --  107.36 -99.00-120.00  112
 17  ω     36.00  70.00   0.50    0.10    --  107.36 -99.00-150.00   68
 18  ω     81.00 106.00   0.50    0.10    --  107.36 -99.00-180.00   50
 19  ω     56.00  82.00   0.50    0.10    --  107.36 -74.00-138.00   52
 20  ω     36.00  69.00   0.50    0.10    --  107.36 -57.00 -60.00   66
 21  ω     38.00  68.00   0.50    0.10    --  107.36 -57.00 150.00   60
 22  ω   -120.00 -88.00   0.50    0.08    --  -47.70-125.00 -30.00   64
 23  ω   -118.00 -27.00   0.50    0.08    --  -47.70 -74.00-138.00  182
 24  ω   -145.00 -91.00   0.50    0.10    -- -104.50 -74.00-138.00  108
 25  ω   -166.00-122.00   0.50    0.10    -- -104.50-125.00 -60.00   88
 26  ω   -105.00 -79.00   0.50    0.10    -- -104.50-125.00 -60.00   52
 27  ω   -174.00 -98.00   0.50    0.10    -- -104.50 -38.00  90.00  152
 28  ω   -171.00-142.00   0.50    0.10    -- -104.50 -19.00   0.00   58
 29  ω   -138.00 -96.00   0.50    0.10    -- -104.50 -19.00   0.00   84
 30  ω    -66.00 -37.00   0.50    0.10    -- -104.50  77.00  60.00   58
 31  ω   -102.00 -71.00   0.50    0.10    -- -104.50  77.00  60.00   62
 32  ω    -92.00 -32.00   0.50    0.10    -- -104.50  74.00 -10.00  120
 33  ω    -80.00 -54.00   0.50    0.10    -- -104.50  77.00 -60.00   52
 34  ω    -62.00 -34.00   0.50    0.10    -- -104.50  57.00-150.00   56
 35  ω    -62.00 -32.00   0.50    0.10    -- -104.50  57.00-180.00   60
 36  ω    -34.00  -8.00   0.50    0.08    --  -47.70  74.00 -10.00   52
 37  ω    -60.00 -35.00   0.50    0.10    -- -104.50  57.00  90.00   50
 38  ω    -62.00 -37.00   0.50    0.10    -- -104.50  57.00 120.00   50
 39  ω    -59.00 -33.00   0.50    0.10    -- -104.50  57.00 150.00   52
 40  ω   -129.00 -66.00   0.50    0.10    -- -104.50 149.00  42.32  126
 41  ω   -110.00 -84.00   0.50    0.10    -- -104.50 125.00   0.00   52
 42  ω    -57.00 -32.00   0.50    0.10    -- -104.50 125.00   0.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1703675000
_diffrn_orient_matrix_UB_12      -0.0504120000
_diffrn_orient_matrix_UB_13      -0.0247039000
_diffrn_orient_matrix_UB_21      0.0177337000
_diffrn_orient_matrix_UB_22      -0.0454027000
_diffrn_orient_matrix_UB_23      0.0889201000
_diffrn_orient_matrix_UB_31      -0.0216183000
_diffrn_orient_matrix_UB_32      0.1225522000
_diffrn_orient_matrix_UB_33      0.0646523000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18336
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.347
_diffrn_reflns_theta_min         3.232
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74041
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light pink'
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_description       block
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         5986
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0292
_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)+(0.0468P)²+0.4012P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0839
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5692
_reflns_number_total             5986
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0308_suppl.cif
_cod_data_source_block           tx10365_auto
_cod_database_code               8107247
_chemical_oxdiff_formula         CHNOClFMn
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
O6 \\sim C25 \\sim O6A \\sim C25A: within 1.7A with sigma of 0.02 and sigma for
terminal atoms of 0.04 within 1.7A
3. Others
 Sof(O6A)=Sof(H6AA)=Sof(C25A)=Sof(H25D)=Sof(H25E)=Sof(H25F)=1-FVAR(1)
 Sof(O6)=Sof(H6A)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(H25C)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), N3(H3A), N5(H5), C2(H2A), C4(H4), C6(H6), C7(H7), C9(H9), C11(H11),
 C13(H13), C14(H14), C16(H16), C18(H18), C20(H20), C21(H21)
4.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C25A(H25D,H25E,
 H25F)
4.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O3(H3), O4(H4A), O5(H5A), O6(H6A), O6A(H6AA)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.282
_oxdiff_exptl_absorpt_empirical_full_min 0.778
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
Cl1 Cl 0.66164(5) 0.18556(3) 0.12521(3) 0.04561(11) Uani 1 1 d . . . . .
Cl2 Cl -0.09921(4) 0.99436(3) 0.20952(3) 0.04146(10) Uani 1 1 d . . . . .
Cl3 Cl 0.77613(4) 0.96687(3) 0.94730(2) 0.04106(10) Uani 1 1 d . . . . .
O1 O 0.88354(11) 0.52448(9) 0.67899(7) 0.0360(2) Uani 1 1 d . . . . .
H1 H 0.951147 0.498117 0.707228 0.054 Uiso 1 1 calc R U . . .
O2 O 0.26637(12) 0.47623(9) -0.01314(7) 0.0367(2) Uani 1 1 d . . . . .
H2 H 0.237084 0.449433 -0.074334 0.055 Uiso 1 1 calc R U . . .
O3 O 0.23621(11) 1.17478(8) 0.61925(7) 0.0321(2) Uani 1 1 d . . . . .
H3 H 0.202833 1.231584 0.652679 0.048 Uiso 1 1 calc R U . . .
N1 N 0.54046(12) 0.65597(9) 0.46849(7) 0.0250(2) Uani 1 1 d . . . . .
H1A H 0.561322 0.588724 0.433015 0.030 Uiso 1 1 calc R U . . .
N2 N 0.59646(11) 0.70307(9) 0.56865(7) 0.0242(2) Uani 1 1 d . . . . .
N3 N 0.40530(11) 0.68274(9) 0.33138(7) 0.0238(2) Uani 1 1 d . . . . .
H3A H 0.349003 0.722790 0.303578 0.029 Uiso 1 1 calc R U . . .
N4 N 0.44751(11) 0.58122(9) 0.27617(7) 0.0242(2) Uani 1 1 d . . . . .
N5 N 0.41405(12) 0.81334(9) 0.48564(7) 0.0249(2) Uani 1 1 d . . . . .
H5 H 0.447451 0.838692 0.549540 0.030 Uiso 1 1 calc R U . . .
N6 N 0.31906(11) 0.87128(9) 0.44088(7) 0.0240(2) Uani 1 1 d . . . . .
C1 C 0.45322(13) 0.71731(10) 0.42812(8) 0.0217(2) Uani 1 1 d . . . . .
C2 C 0.68857(14) 0.64710(11) 0.60325(9) 0.0262(2) Uani 1 1 d . . . . .
H2A H 0.709754 0.576569 0.560963 0.031 Uiso 1 1 calc R U . . .
C3 C 0.76136(13) 0.69054(11) 0.70701(9) 0.0252(2) Uani 1 1 d . . . . .
C4 C 0.73543(14) 0.79538(11) 0.77063(9) 0.0272(3) Uani 1 1 d . . . . .
H4 H 0.667221 0.838575 0.747037 0.033 Uiso 1 1 calc R U . . .
C5 C 0.80885(15) 0.83617(12) 0.86769(9) 0.0302(3) Uani 1 1 d . . . . .
C6 C 0.90966(16) 0.77488(13) 0.90348(10) 0.0363(3) Uani 1 1 d . . . . .
H6 H 0.960310 0.804427 0.970474 0.044 Uiso 1 1 calc R U . . .
C7 C 0.93604(15) 0.67087(13) 0.84138(10) 0.0346(3) Uani 1 1 d . . . . .
H7 H 1.004783 0.628599 0.865735 0.041 Uiso 1 1 calc R U . . .
C8 C 0.86217(14) 0.62765(12) 0.74305(10) 0.0281(3) Uani 1 1 d . . . . .
C9 C 0.39335(14) 0.54939(11) 0.18402(9) 0.0257(2) Uani 1 1 d . . . . .
H9 H 0.332087 0.596329 0.159111 0.031 Uiso 1 1 calc R U . . .
C10 C 0.42423(14) 0.44201(11) 0.11654(9) 0.0260(2) Uani 1 1 d . . . . .
C11 C 0.51707(14) 0.37243(11) 0.14974(9) 0.0279(3) Uani 1 1 d . . . . .
H11 H 0.562633 0.394950 0.217312 0.033 Uiso 1 1 calc R U . . .
C12 C 0.54232(16) 0.27096(12) 0.08405(10) 0.0326(3) Uani 1 1 d . . . . .
C13 C 0.47444(18) 0.23478(13) -0.01452(10) 0.0381(3) Uani 1 1 d . . . . .
H13 H 0.491472 0.163695 -0.058655 0.046 Uiso 1 1 calc R U . . .
C14 C 0.38191(17) 0.30248(13) -0.04833(10) 0.0354(3) Uani 1 1 d . . . . .
H14 H 0.335284 0.277986 -0.115869 0.042 Uiso 1 1 calc R U . . .
C15 C 0.35678(15) 0.40682(12) 0.01657(9) 0.0289(3) Uani 1 1 d . . . . .
C16 C 0.28616(14) 0.96367(11) 0.49841(9) 0.0257(2) Uani 1 1 d . . . . .
H16 H 0.329460 0.989287 0.566521 0.031 Uiso 1 1 calc R U . . .
C17 C 0.18291(13) 1.03014(11) 0.46062(9) 0.0248(2) Uani 1 1 d . . . . .
C18 C 0.10420(14) 0.98776(11) 0.36259(9) 0.0277(3) Uani 1 1 d . . . . .
H18 H 0.121806 0.917093 0.318264 0.033 Uiso 1 1 calc R U . . .
C19 C 0.00126(14) 1.04895(12) 0.33078(10) 0.0295(3) Uani 1 1 d . . . . .
C20 C -0.02548(15) 1.15270(12) 0.39405(11) 0.0327(3) Uani 1 1 d . . . . .
H20 H -0.096956 1.193809 0.371023 0.039 Uiso 1 1 calc R U . . .
C21 C 0.05215(15) 1.19622(12) 0.49080(10) 0.0312(3) Uani 1 1 d . . . . .
H21 H 0.034503 1.267657 0.534124 0.037 Uiso 1 1 calc R U . . .
C22 C 0.15622(14) 1.13545(11) 0.52481(9) 0.0259(2) Uani 1 1 d . . . . .
Cl4 Cl -0.13211(3) 0.60410(3) 0.24272(2) 0.03116(9) Uani 1 1 d . . . . .
O4 O 0.72925(13) 0.50240(9) 0.39093(8) 0.0394(2) Uani 1 1 d . . . . .
H4A H 0.764360 0.524568 0.348195 0.059 Uiso 1 1 calc R U . . .
C23 C 0.7849(2) 0.40109(15) 0.40234(13) 0.0447(4) Uani 1 1 d . . . . .
H23A H 0.728822 0.327590 0.349158 0.067 Uiso 1 1 calc R U . . .
H23B H 0.773275 0.392190 0.465238 0.067 Uiso 1 1 calc R U . . .
H23C H 0.891222 0.413050 0.400547 0.067 Uiso 1 1 calc R U . . .
O5 O 0.16415(11) 0.72976(10) 0.20877(7) 0.0384(2) Uani 1 1 d . . . . .
H5A H 0.087527 0.701953 0.225399 0.058 Uiso 1 1 calc R U . . .
C24 C 0.1235(2) 0.73236(18) 0.11198(12) 0.0506(4) Uani 1 1 d . . . . .
H24A H 0.051216 0.657412 0.071530 0.076 Uiso 1 1 calc R U . . .
H24B H 0.212972 0.738943 0.084972 0.076 Uiso 1 1 calc R U . . .
H24C H 0.078095 0.802526 0.112483 0.076 Uiso 1 1 calc R U . . .
O6 O 0.44043(16) 0.91932(12) 0.69584(9) 0.0378(4) Uani 0.776(3) 1 d . U P A 1
H6A H 0.401499 0.891210 0.734590 0.057 Uiso 0.776(3) 1 calc R U P A 1
C25 C 0.5144(6) 1.0382(5) 0.7439(4) 0.0496(14) Uani 0.776(3) 1 d . U P A 1
H25A H 0.581853 1.063958 0.705485 0.074 Uiso 0.776(3) 1 calc R U P A 1
H25B H 0.572862 1.044965 0.808221 0.074 Uiso 0.776(3) 1 calc R U P A 1
H25C H 0.441286 1.090370 0.752128 0.074 Uiso 0.776(3) 1 calc R U P A 1
O6A O 0.5538(5) 0.9895(4) 0.6780(3) 0.0375(14) Uani 0.224(3) 1 d . U P A 2
H6AA H 0.610989 1.031171 0.655511 0.056 Uiso 0.224(3) 1 calc R U P A 2
C25A C 0.523(3) 1.057(2) 0.7509(19) 0.072(7) Uani 0.224(3) 1 d . U P A 2
H25D H 0.485257 1.123396 0.734595 0.108 Uiso 0.224(3) 1 calc R U P A 2
H25E H 0.613737 1.090115 0.803708 0.108 Uiso 0.224(3) 1 calc R U P A 2
H25F H 0.446680 1.010026 0.772157 0.108 Uiso 0.224(3) 1 calc R U P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C8 O1 H1 109.5 . .
C15 O2 H2 109.5 . .
C22 O3 H3 109.5 . .
N2 N1 H1A 121.5 . .
C1 N1 H1A 121.5 . .
C1 N1 N2 116.94(9) . .
C2 N2 N1 114.94(10) . .
N4 N3 H3A 121.3 . .
C1 N3 H3A 121.3 . .
C1 N3 N4 117.41(10) . .
C9 N4 N3 114.65(10) . .
N6 N5 H5 121.2 . .
C1 N5 H5 121.2 . .
C1 N5 N6 117.53(9) . .
C16 N6 N5 115.49(10) . .
N1 C1 N5 119.55(10) . .
N3 C1 N1 120.14(10) . .
N3 C1 N5 120.31(10) . .
N2 C2 H2A 119.7 . .
N2 C2 C3 120.64(11) . .
C3 C2 H2A 119.7 . .
C4 C3 C2 121.12(11) . .
C4 C3 C8 119.35(11) . .
C8 C3 C2 119.50(11) . .
C3 C4 H4 120.1 . .
C5 C4 C3 119.88(12) . .
C5 C4 H4 120.1 . .
C4 C5 Cl3 119.92(10) . .
C4 C5 C6 120.97(12) . .
C6 C5 Cl3 119.11(10) . .
C5 C6 H6 120.1 . .
C7 C6 C5 119.73(12) . .
C7 C6 H6 120.1 . .
C6 C7 H7 119.9 . .
C6 C7 C8 120.19(12) . .
C8 C7 H7 119.9 . .
O1 C8 C3 117.82(11) . .
O1 C8 C7 122.31(12) . .
C7 C8 C3 119.87(12) . .
N4 C9 H9 119.5 . .
N4 C9 C10 121.05(11) . .
C10 C9 H9 119.5 . .
C11 C10 C9 121.35(11) . .
C11 C10 C15 119.39(11) . .
C15 C10 C9 119.25(11) . .
C10 C11 H11 120.1 . .
C12 C11 C10 119.71(12) . .
C12 C11 H11 120.1 . .
C11 C12 Cl1 119.73(11) . .
C11 C12 C13 121.18(13) . .
C13 C12 Cl1 119.09(10) . .
C12 C13 H13 120.1 . .
C14 C13 C12 119.72(12) . .
C14 C13 H13 120.1 . .
C13 C14 H14 119.9 . .
C13 C14 C15 120.11(12) . .
C15 C14 H14 119.9 . .
O2 C15 C10 117.84(11) . .
O2 C15 C14 122.29(12) . .
C14 C15 C10 119.87(12) . .
N6 C16 H16 119.6 . .
N6 C16 C17 120.82(11) . .
C17 C16 H16 119.6 . .
C18 C17 C16 121.32(11) . .
C18 C17 C22 119.24(11) . .
C22 C17 C16 119.37(11) . .
C17 C18 H18 120.1 . .
C19 C18 C17 119.76(12) . .
C19 C18 H18 120.1 . .
C18 C19 Cl2 119.69(10) . .
C18 C19 C20 121.09(12) . .
C20 C19 Cl2 119.22(10) . .
C19 C20 H20 120.1 . .
C21 C20 C19 119.84(12) . .
C21 C20 H20 120.1 . .
C20 C21 H21 119.9 . .
C20 C21 C22 120.11(12) . .
C22 C21 H21 119.9 . .
O3 C22 C17 117.57(11) . .
O3 C22 C21 122.47(11) . .
C21 C22 C17 119.96(12) . .
C23 O4 H4A 109.5 . .
O4 C23 H23A 109.5 . .
O4 C23 H23B 109.5 . .
O4 C23 H23C 109.5 . .
H23A C23 H23B 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C24 O5 H5A 109.5 . .
O5 C24 H24A 109.5 . .
O5 C24 H24B 109.5 . .
O5 C24 H24C 109.5 . .
H24A C24 H24B 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
C25 O6 H6A 109.5 . .
O6 C25 H25A 109.5 . .
O6 C25 H25B 109.5 . .
O6 C25 H25C 109.5 . .
H25A C25 H25B 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
C25A O6A H6AA 109.5 . .
O6A C25A H25D 109.5 . .
O6A C25A H25E 109.5 . .
O6A C25A H25F 109.5 . .
H25D C25A H25E 109.5 . .
H25D C25A H25F 109.5 . .
H25E C25A H25F 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C12 1.7488(14) .
Cl2 C19 1.7426(13) .
Cl3 C5 1.7421(14) .
O1 H1 0.8400 .
O1 C8 1.3662(17) .
O2 H2 0.8400 .
O2 C15 1.3595(16) .
O3 H3 0.8400 .
O3 C22 1.3630(15) .
N1 H1A 0.8800 .
N1 N2 1.3841(13) .
N1 C1 1.3370(15) .
N2 C2 1.2794(16) .
N3 H3A 0.8800 .
N3 N4 1.3857(14) .
N3 C1 1.3313(15) .
N4 C9 1.2798(16) .
N5 H5 0.8800 .
N5 N6 1.3843(13) .
N5 C1 1.3388(15) .
N6 C16 1.2803(16) .
C2 H2A 0.9500 .
C2 C3 1.4587(17) .
C3 C4 1.3946(18) .
C3 C8 1.4030(17) .
C4 H4 0.9500 .
C4 C5 1.3769(17) .
C5 C6 1.3875(19) .
C6 H6 0.9500 .
C6 C7 1.380(2) .
C7 H7 0.9500 .
C7 C8 1.3932(18) .
C9 H9 0.9500 .
C9 C10 1.4609(17) .
C10 C11 1.3963(18) .
C10 C15 1.4038(17) .
C11 H11 0.9500 .
C11 C12 1.3780(18) .
C12 C13 1.386(2) .
C13 H13 0.9500 .
C13 C14 1.381(2) .
C14 H14 0.9500 .
C14 C15 1.3957(19) .
C16 H16 0.9500 .
C16 C17 1.4603(16) .
C17 C18 1.4021(18) .
C17 C22 1.4052(17) .
C18 H18 0.9500 .
C18 C19 1.3776(18) .
C19 C20 1.3863(19) .
C20 H20 0.9500 .
C20 C21 1.383(2) .
C21 H21 0.9500 .
C21 C22 1.3938(18) .
O4 H4A 0.8400 .
O4 C23 1.4093(17) .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
O5 H5A 0.8400 .
O5 C24 1.4165(18) .
C24 H24A 0.9800 .
C24 H24B 0.9800 .
C24 H24C 0.9800 .
O6 H6A 0.8400 .
O6 C25 1.377(6) .
C25 H25A 0.9800 .
C25 H25B 0.9800 .
C25 H25C 0.9800 .
O6A H6AA 0.8400 .
O6A C25A 1.23(3) .
C25A H25D 0.9800 .
C25A H25E 0.9800 .
C25A H25F 0.9800 .
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
N1 H1A O4 0.88 2.07 2.8370(14) 145.7 . yes
N3 H3A O5 0.88 2.04 2.8502(14) 151.9 . yes
N5 H5 O6 0.88 2.10 2.9215(16) 156.1 . yes
N5 H5 O6A 0.88 2.14 2.913(5) 146.6 . yes
O6A H6AA N6 0.84 2.18 2.982(5) 158.7 2_676 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
Cl1 C12 C13 C14 -178.93(12) . . . .
Cl2 C19 C20 C21 179.22(11) . . . .
Cl3 C5 C6 C7 179.64(11) . . . .
N1 N2 C2 C3 177.15(10) . . . .
N2 N1 C1 N3 174.65(11) . . . .
N2 N1 C1 N5 -5.60(17) . . . .
N2 C2 C3 C4 -1.52(19) . . . .
N2 C2 C3 C8 -179.86(12) . . . .
N3 N4 C9 C10 -178.22(10) . . . .
N4 N3 C1 N1 0.98(17) . . . .
N4 N3 C1 N5 -178.77(10) . . . .
N4 C9 C10 C11 -1.82(19) . . . .
N4 C9 C10 C15 176.92(12) . . . .
N5 N6 C16 C17 -177.88(11) . . . .
N6 N5 C1 N1 -177.63(11) . . . .
N6 N5 C1 N3 2.12(17) . . . .
N6 C16 C17 C18 7.02(19) . . . .
N6 C16 C17 C22 -176.17(12) . . . .
C1 N1 N2 C2 -174.81(11) . . . .
C1 N3 N4 C9 177.34(11) . . . .
C1 N5 N6 C16 -179.04(11) . . . .
C2 C3 C4 C5 -178.20(12) . . . .
C2 C3 C8 O1 -2.42(18) . . . .
C2 C3 C8 C7 177.82(12) . . . .
C3 C4 C5 Cl3 -179.82(10) . . . .
C3 C4 C5 C6 0.4(2) . . . .
C4 C3 C8 O1 179.20(11) . . . .
C4 C3 C8 C7 -0.56(19) . . . .
C4 C5 C6 C7 -0.6(2) . . . .
C5 C6 C7 C8 0.2(2) . . . .
C6 C7 C8 O1 -179.36(13) . . . .
C6 C7 C8 C3 0.4(2) . . . .
C8 C3 C4 C5 0.14(19) . . . .
C9 C10 C11 C12 179.29(12) . . . .
C9 C10 C15 O2 0.85(18) . . . .
C9 C10 C15 C14 -178.19(12) . . . .
C10 C11 C12 Cl1 178.69(10) . . . .
C10 C11 C12 C13 -1.5(2) . . . .
C11 C10 C15 O2 179.63(11) . . . .
C11 C10 C15 C14 0.58(19) . . . .
C11 C12 C13 C14 1.2(2) . . . .
C12 C13 C14 C15 -0.1(2) . . . .
C13 C14 C15 O2 -179.82(13) . . . .
C13 C14 C15 C10 -0.8(2) . . . .
C15 C10 C11 C12 0.55(19) . . . .
C16 C17 C18 C19 176.26(12) . . . .
C16 C17 C22 O3 3.94(17) . . . .
C16 C17 C22 C21 -176.69(12) . . . .
C17 C18 C19 Cl2 -178.70(10) . . . .
C17 C18 C19 C20 0.4(2) . . . .
C18 C17 C22 O3 -179.17(11) . . . .
C18 C17 C22 C21 0.19(18) . . . .
C18 C19 C20 C21 0.1(2) . . . .
C19 C20 C21 C22 -0.5(2) . . . .
C20 C21 C22 O3 179.66(12) . . . .
C20 C21 C22 C17 0.3(2) . . . .
C22 C17 C18 C19 -0.56(19) . . . .
