#------------------------------------------------------------------------------
#$Date: 2024-12-07 19:04:45 +0200 (Sat, 07 Dec 2024) $
#$Revision: 296757 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/27/2312716.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_2312716
loop_
_publ_author_name
'Kanthapazham, Rajakumar'
'Osipov, Artyom A.'
'Zherebtsov, Dmitry A.'
'Efremov, Andrey N.'
'Nayfert, Sergey A.'
'Adonin, Sergey A.'
'Spiridonova, Dar'ya V.'
'Atapin, Sergey V.'
_publ_section_title
;
 Structures of hexamethyl-[1,1'-biphenyl]-4,4'-diammonium salts.
;
_journal_coeditor_code           AW5097
_journal_issue                   6
_journal_name_full
'Acta crystallographica Section B, Structural science, crystal engineering and materials'
_journal_page_first              751
_journal_page_last               759
_journal_paper_doi               10.1107/S2052520624009818
_journal_volume                  80
_journal_year                    2024
_chemical_formula_moiety         'C24 H8 O8, 10(H2 O), 2(C18 H26 N2)'
_chemical_formula_sum            'C60 H80 N4 O18'
_chemical_formula_weight         1145.28
_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_date             2024-07-02
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_cell_angle_alpha                92.431(3)
_cell_angle_beta                 90.386(3)
_cell_angle_gamma                113.564(4)
_cell_formula_units_Z            1
_cell_length_a                   10.0218(4)
_cell_length_b                   11.3143(4)
_cell_length_c                   13.6143(4)
_cell_measurement_reflns_used    8305
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.4870
_cell_measurement_theta_min      3.2490
_cell_volume                     1413.25(10)
_computing_cell_refinement       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.115a (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 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -47.00  24.00   0.50   40.00    --  -47.13  52.00-119.00  142
  2  ω   -118.00 -53.00   0.50   40.00    --  -47.13 -52.00  95.00  130
  3  ω    -21.00  28.00   0.50   40.00    --   47.13 -52.00  95.00   98
  4  ω     72.00 100.00   0.50   40.00    --   47.13  52.00-119.00   56
  5  ω   -176.00 -94.00   0.50   40.00    -- -106.00 -52.00  95.00  164
  6  ω    -58.00 -33.00   0.50   40.00    -- -106.00  52.00-119.00   50
  7  ω    101.00 178.00   0.50   40.00    --  113.25  52.00-119.00  154
  8  ω   -119.00 -94.00   0.50   40.00    --  -47.13-125.00  30.00   50
  9  ω    -95.00 -14.00   0.50   40.00    --  -47.13 125.00   0.00  162
 10  ω    -27.00   7.00   0.50   40.00    --   47.13 -19.00 -60.00   68
 11  ω     76.00 119.00   0.50   40.00    --   47.13 125.00  90.00   86
 12  ω      2.00  70.00   0.50   40.00    --   47.13 -77.00-180.00  136
 13  ω      8.00  37.00   0.50   40.00    --   47.13 -37.00  30.00   58
 14  ω    -63.00 -35.00   0.50   40.00    -- -106.00 106.00-124.68   56
 15  ω    -98.00 -47.00   0.50   40.00    -- -106.00  77.00-180.00  102
 16  ω   -170.00 -94.00   0.50   40.00    -- -106.00 -61.00-180.00  152
 17  ω    -71.00 -35.00   0.50   40.00    -- -106.00  61.00-120.00   72
 18  ω   -126.00 -85.00   0.50   40.00    -- -106.00 145.00  57.38   82
 19  ω   -108.00 -33.00   0.50   40.00    -- -106.00 109.00 167.60  150
 20  ω   -107.00 -81.00   0.50   40.00    -- -106.00 106.00-124.68   52
 21  ω   -108.00 -61.00   0.50   40.00    -- -106.00 110.00 -71.01   94
 22  ω   -109.00 -54.00   0.50   40.00    -- -106.00 115.00 -43.04  110
 23  ω    -66.00 -33.00   0.50   40.00    -- -106.00 125.00-120.00   66
 24  ω    -76.00 -50.00   0.50   40.00    -- -106.00 143.00-140.87   52
 25  ω    -83.00 -39.00   0.50   40.00    -- -106.00 125.00   0.00   88
 26  ω   -123.00 -79.00   0.50   40.00    -- -106.00 143.00-140.87   88
 27  ω   -111.00 -64.00   0.50   40.00    -- -106.00 125.00-150.00   94
 28  ω   -101.00 -76.00   0.50   40.00    -- -106.00  77.00  60.00   50
 29  ω    -58.00 -33.00   0.50   40.00    -- -106.00 136.00  -5.57   50
 30  ω   -108.00 -47.00   0.50   40.00    -- -106.00 109.00 110.09  122
 31  ω    -69.00 -43.00   0.50   40.00    -- -106.00 145.00  57.38   52
 32  ω   -120.00 -72.00   0.50   40.00    -- -106.00 136.00  -5.57   96
 33  ω   -112.00 -86.00   0.50   40.00    -- -106.00 125.00   0.00   52
 34  ω    123.00 165.00   0.50   40.00    --  113.25  45.00 150.00   84
 35  ω     52.00 109.00   0.50   40.00    --  113.25-125.00   0.00  114
 36  ω     55.00  95.00   0.50   40.00    --  113.25 -77.00-180.00   80
 37  ω     46.00  79.00   0.50   40.00    --  113.25 -94.00  30.00   66
 38  ω     91.00 173.00   0.50   40.00    --  113.25  77.00  90.00  164
 39  ω    103.00 178.00   0.50   40.00    --  113.25  30.00   0.00  150
 40  ω     61.00 107.00   0.50   40.00    --  113.25-107.00 154.52   92
 41  ω     70.00  95.00   0.50   40.00    --  113.25 -77.00-150.00   50
 42  ω    103.00 169.00   0.50   40.00    --  113.25  30.00  30.00  132
 43  ω     46.00  86.00   0.50   40.00    --  113.25 -77.00 -30.00   80
 44  ω     42.00  67.00   0.50   40.00    --  113.25 -61.00  60.00   50
 45  ω     71.00  97.00   0.50   40.00    --  113.25-125.00 -30.00   52
 46  ω    136.00 161.00   0.50   40.00    --  113.25  45.00 -60.00   50
 47  ω    105.00 133.00   0.50   40.00    --  113.25  45.00 -60.00   56
 48  ω     44.00  69.00   0.50   40.00    --  113.25-125.00 -90.00   50
 49  ω     86.00 111.00   0.50   40.00    --  113.25-125.00 -90.00   50
 50  ω    101.00 161.00   0.50   40.00    --  113.25  45.00-180.00  120
 51  ω    100.00 139.00   0.50   40.00    --  113.25  15.00-180.00   78
 52  ω     46.00 121.00   0.50   40.00    --  113.25-137.00 119.95  150
 53  ω     73.00  99.00   0.50   40.00    --  113.25-125.00 120.00   52
 54  ω     45.00  70.00   0.50   40.00    --  113.25 -61.00   0.00   50
 55  ω     43.00  70.00   0.50   40.00    --  113.25 -61.00-120.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1381366000
_diffrn_orient_matrix_UB_12      -0.0932709000
_diffrn_orient_matrix_UB_13      -0.0566426000
_diffrn_orient_matrix_UB_21      0.0831137000
_diffrn_orient_matrix_UB_22      -0.0810398000
_diffrn_orient_matrix_UB_23      -0.0376150000
_diffrn_orient_matrix_UB_31      -0.0464137000
_diffrn_orient_matrix_UB_32      -0.0827820000
_diffrn_orient_matrix_UB_33      0.0906260000
_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  0.0430
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18105
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.000
_diffrn_reflns_theta_min         3.250
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.822
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49450
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.115a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       prism
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         5307
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0686
_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)+(0.1171P)²+1.3826P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1999
_refine_ls_wR_factor_ref         0.2100
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4336
_reflns_number_total             5307
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            aw5097sup1.cif
_cod_data_source_block           hmbc-petk
_cod_depositor_comments
'Adding full bibliography for 2312709--2312717.cif.'
_cod_original_cell_volume        1413.25(9)
_cod_database_code               2312716
_cod_database_fobs_code          2312716
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C43 H34 N2 O11 K4'
_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   0.968
_shelx_estimated_absorpt_t_min   0.945
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 H7e-H6a
 2.5 with sigma of 0.02
3.a Free rotating group:
 O5(H5a,H5b), O7(H7d,H7e), O8(H8d,H8e), O6(H6a,H6b), O9(H9d,H9e)
3.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C22(H22), C23(H23), C6(H6), C28(H28), C29(H29), C5(H5), C2(H2),
 C13(H13), C16(H16), C3(H3), C15(H15)
3.c Idealised Me refined as rotating group:
 C9(H9a,H9b,H9c), C19(H19a,H19b,H19c), C8(H8a,H8b,H8c), C7(H7a,H7b,H7c),
 C17(H17a,H17b,H17c), C18(H18a,H18b,H18c)
;
_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 2.211
_oxdiff_exptl_absorpt_empirical_full_min 0.570
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
O2 O 0.9441(2) 0.76797(19) 0.22626(15) 0.0232(5) Uani 1 1 d . . . . .
O3 O 0.6546(2) 0.74748(19) 0.13412(15) 0.0244(5) Uani 1 1 d . . . . .
O1 O 0.9350(2) 0.95273(18) 0.28416(16) 0.0250(5) Uani 1 1 d . . . . .
O5 O 1.1849(2) 1.12615(19) 0.22110(15) 0.0246(5) Uani 1 1 d G . . . .
H5A H 1.099861 1.067494 0.234048 0.037 Uiso 1 1 d G U . . .
H5B H 1.183719 1.130415 0.157485 0.037 Uiso 1 1 d G U . . .
O4 O 0.7024(2) 0.58236(19) 0.07313(15) 0.0265(5) Uani 1 1 d . . . . .
O7 O 1.0758(3) 0.8602(2) 0.05545(16) 0.0303(5) Uani 1 1 d G . . . .
H7D H 1.038542 0.841593 0.113195 0.046 Uiso 1 1 d G U . . .
H7E H 1.133538 0.941604 0.061690 0.046 Uiso 1 1 d DG U . . .
O8 O 0.6046(3) 0.3421(2) -0.01375(18) 0.0316(5) Uani 1 1 d G . . . .
H8D H 0.619747 0.416083 0.015993 0.047 Uiso 1 1 d G U . . .
H8E H 0.518520 0.317378 -0.041176 0.047 Uiso 1 1 d G U . . .
O6 O 0.8187(3) 0.8740(2) -0.01815(16) 0.0306(5) Uani 1 1 d G . . . .
H6A H 0.886913 0.845276 -0.012812 0.046 Uiso 1 1 d DG U . . .
H6B H 0.758627 0.837492 0.028009 0.046 Uiso 1 1 d G U . . .
O9 O 0.7435(3) 0.2050(2) 0.06724(17) 0.0356(6) Uani 1 1 d G . . . .
H9D H 0.703107 0.251574 0.040675 0.053 Uiso 1 1 d G U . . .
H9E H 0.796889 0.192391 0.021184 0.053 Uiso 1 1 d G U . . .
N1 N 0.5144(3) 1.0011(2) 0.24758(17) 0.0205(5) Uani 1 1 d . . . . .
N2 N -0.0793(3) 0.5187(2) 0.80467(18) 0.0228(6) Uani 1 1 d . . . . .
C26 C 0.6644(3) 0.6357(3) 0.3345(2) 0.0184(6) Uani 1 1 d . . . . .
C25 C 0.5835(3) 0.5683(3) 0.4170(2) 0.0181(6) Uani 1 1 d . . . . .
C31 C 0.8940(3) 0.8327(3) 0.2798(2) 0.0201(6) Uani 1 1 d . . . . .
C32 C 0.6687(3) 0.6421(3) 0.1412(2) 0.0212(6) Uani 1 1 d . . . . .
C30 C 0.4662(3) 0.4432(3) 0.4018(2) 0.0183(6) Uani 1 1 d . . . . .
C24 C 0.6166(3) 0.6256(3) 0.5144(2) 0.0180(6) Uani 1 1 d . . . . .
C1 C 0.4204(3) 0.9209(3) 0.3256(2) 0.0206(6) Uani 1 1 d . . . . .
C14 C 0.1523(3) 0.7040(3) 0.5528(2) 0.0202(6) Uani 1 1 d . . . . .
C12 C -0.0063(3) 0.6974(3) 0.6881(2) 0.0226(6) Uani 1 1 d . . . . .
H12 H -0.061642 0.734773 0.724307 0.027 Uiso 1 1 calc R U . . .
C21 C 0.7811(3) 0.7591(3) 0.3534(2) 0.0180(6) Uani 1 1 d . . . . .
C4 C 0.2427(3) 0.7758(3) 0.4718(2) 0.0212(6) Uani 1 1 d . . . . .
C22 C 0.8040(3) 0.8131(3) 0.4476(2) 0.0201(6) Uani 1 1 d . . . . .
H22 H 0.877087 0.897718 0.458981 0.024 Uiso 1 1 calc R U . . .
C23 C 0.7248(3) 0.7493(3) 0.5276(2) 0.0201(6) Uani 1 1 d . . . . .
H23 H 0.745085 0.790871 0.591324 0.024 Uiso 1 1 calc R U . . .
C27 C 0.6213(3) 0.5761(3) 0.2378(2) 0.0196(6) Uani 1 1 d . . . . .
C6 C 0.4678(3) 0.8454(3) 0.3821(2) 0.0240(6) Uani 1 1 d . . . . .
H6 H 0.560240 0.842809 0.371738 0.029 Uiso 1 1 calc R U . . .
C28 C 0.5111(3) 0.4546(3) 0.2273(2) 0.0216(6) Uani 1 1 d . . . . .
H28 H 0.486371 0.413654 0.163462 0.026 Uiso 1 1 calc R U . . .
C29 C 0.4348(3) 0.3896(3) 0.3074(2) 0.0219(6) Uani 1 1 d . . . . .
H29 H 0.359133 0.306169 0.296529 0.026 Uiso 1 1 calc R U . . .
C5 C 0.3775(3) 0.7734(3) 0.4541(2) 0.0233(6) Uani 1 1 d . . . . .
H5 H 0.409351 0.720883 0.492403 0.028 Uiso 1 1 calc R U . . .
C2 C 0.2849(3) 0.9235(3) 0.3399(2) 0.0225(6) Uani 1 1 d . . . . .
H2 H 0.252417 0.974301 0.300181 0.027 Uiso 1 1 calc R U . . .
C11 C 0.0000(3) 0.5834(3) 0.7161(2) 0.0205(6) Uani 1 1 d . . . . .
C13 C 0.0692(3) 0.7563(3) 0.6065(2) 0.0223(6) Uani 1 1 d . . . . .
H13 H 0.064184 0.833930 0.586694 0.027 Uiso 1 1 calc R U . . .
C16 C 0.0771(3) 0.5259(3) 0.6618(2) 0.0238(6) Uani 1 1 d . . . . .
H16 H 0.078054 0.446084 0.679973 0.029 Uiso 1 1 calc R U . . .
C3 C 0.1970(3) 0.8518(3) 0.4125(2) 0.0221(6) Uani 1 1 d . . . . .
H3 H 0.104304 0.854126 0.422278 0.026 Uiso 1 1 calc R U . . .
C15 C 0.1520(3) 0.5864(3) 0.5813(2) 0.0242(6) Uani 1 1 d . . . . .
H15 H 0.204867 0.547427 0.544164 0.029 Uiso 1 1 calc R U . . .
C9 C 0.5307(3) 1.1392(3) 0.2630(2) 0.0257(7) Uani 1 1 d . . . . .
H9A H 0.435800 1.143482 0.253298 0.039 Uiso 1 1 calc R U . . .
H9B H 0.599222 1.192781 0.215667 0.039 Uiso 1 1 calc R U . . .
H9C H 0.567735 1.170947 0.330016 0.039 Uiso 1 1 calc R U . . .
C19 C -0.1241(3) 0.6069(3) 0.8695(2) 0.0253(6) Uani 1 1 d . . . . .
H19A H -0.038256 0.685342 0.888243 0.038 Uiso 1 1 calc R U . . .
H19B H -0.168639 0.562774 0.928789 0.038 Uiso 1 1 calc R U . . .
H19C H -0.194698 0.630077 0.833727 0.038 Uiso 1 1 calc R U . . .
C8 C 0.6642(3) 1.0007(3) 0.2485(2) 0.0262(7) Uani 1 1 d . . . . .
H8A H 0.709869 1.029842 0.313886 0.039 Uiso 1 1 calc R U . . .
H8B H 0.723370 1.059070 0.199559 0.039 Uiso 1 1 calc R U . . .
H8C H 0.656957 0.913073 0.232537 0.039 Uiso 1 1 calc R U . . .
C7 C 0.4444(4) 0.9499(3) 0.1474(2) 0.0279(7) Uani 1 1 d . . . . .
H7A H 0.436374 0.861284 0.135579 0.042 Uiso 1 1 calc R U . . .
H7B H 0.504264 1.004454 0.096845 0.042 Uiso 1 1 calc R U . . .
H7C H 0.347046 0.950873 0.144856 0.042 Uiso 1 1 calc R U . . .
C17 C 0.0160(4) 0.4744(3) 0.8665(2) 0.0320(7) Uani 1 1 d . . . . .
H17A H 0.044461 0.414204 0.826955 0.048 Uiso 1 1 calc R U . . .
H17B H -0.037972 0.430950 0.923399 0.048 Uiso 1 1 calc R U . . .
H17C H 0.103358 0.549223 0.889122 0.048 Uiso 1 1 calc R U . . .
C18 C -0.2140(4) 0.4044(3) 0.7702(3) 0.0358(8) Uani 1 1 d . . . . .
H18A H -0.272039 0.432745 0.726188 0.054 Uiso 1 1 calc R U . . .
H18B H -0.271678 0.365243 0.827078 0.054 Uiso 1 1 calc R U . . .
H18C H -0.186169 0.340817 0.734870 0.054 Uiso 1 1 calc R U . . .
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'
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
_geom_angle_publ_flag
H5A O5 H5B 104.6 . . ?
H7D O7 H7E 104.5 . . ?
H8D O8 H8E 104.6 . . ?
H6A O6 H6B 104.5 . . ?
H9D O9 H9E 104.5 . . ?
C1 N1 C9 109.7(2) . . ?
C1 N1 C8 112.6(2) . . ?
C1 N1 C7 109.7(2) . . ?
C9 N1 C7 108.7(2) . . ?
C8 N1 C9 107.9(2) . . ?
C8 N1 C7 108.1(2) . . ?
C11 N2 C19 112.4(2) . . ?
C11 N2 C17 110.5(2) . . ?
C11 N2 C18 108.3(2) . . ?
C19 N2 C17 107.4(2) . . ?
C18 N2 C19 108.5(2) . . ?
C18 N2 C17 109.8(3) . . ?
C21 C26 C25 118.4(3) . . ?
C21 C26 C27 123.5(3) . . ?
C27 C26 C25 118.2(2) . . ?
C30 C25 C26 120.3(3) . . ?
C24 C25 C26 120.7(2) . . ?
C24 C25 C30 119.0(2) . . ?
O2 C31 C21 116.7(2) . . ?
O1 C31 O2 126.7(3) . . ?
O1 C31 C21 116.4(2) . . ?
O3 C32 C27 115.7(2) . . ?
O4 C32 O3 125.7(3) . . ?
O4 C32 C27 118.1(2) . . ?
C25 C30 C24 120.5(3) . 2_666 ?
C29 C30 C25 118.3(3) . . ?
C29 C30 C24 121.2(2) . 2_666 ?
C25 C24 C30 120.5(2) . 2_666 ?
C23 C24 C25 118.5(3) . . ?
C23 C24 C30 120.9(3) . 2_666 ?
C6 C1 N1 120.8(3) . . ?
C2 C1 N1 118.6(3) . . ?
C2 C1 C6 120.6(3) . . ?
C13 C14 C4 119.9(3) . . ?
C13 C14 C15 117.8(3) . . ?
C15 C14 C4 122.2(3) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C13 C12 C11 119.1(3) . . ?
C26 C21 C31 125.6(3) . . ?
C22 C21 C26 118.7(2) . . ?
C22 C21 C31 115.4(2) . . ?
C5 C4 C14 120.9(3) . . ?
C5 C4 C3 117.7(3) . . ?
C3 C4 C14 121.3(3) . . ?
C21 C22 H22 118.4 . . ?
C21 C22 C23 123.1(2) . . ?
C23 C22 H22 118.4 . . ?
C24 C23 C22 120.4(3) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C26 C27 C32 126.0(2) . . ?
C28 C27 C26 119.2(3) . . ?
C28 C27 C32 114.1(3) . . ?
C1 C6 H6 120.6 . . ?
C1 C6 C5 118.8(3) . . ?
C5 C6 H6 120.6 . . ?
C27 C28 H28 118.9 . . ?
C27 C28 C29 122.1(3) . . ?
C29 C28 H28 118.9 . . ?
C30 C29 C28 121.7(3) . . ?
C30 C29 H29 119.1 . . ?
C28 C29 H29 119.1 . . ?
C4 C5 C6 122.1(3) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.7(3) . . ?
C3 C2 H2 120.1 . . ?
C12 C11 N2 120.1(3) . . ?
C12 C11 C16 120.9(3) . . ?
C16 C11 N2 118.9(3) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 C14 121.5(3) . . ?
C12 C13 H13 119.3 . . ?
C11 C16 H16 120.5 . . ?
C15 C16 C11 119.0(3) . . ?
C15 C16 H16 120.5 . . ?
C4 C3 H3 119.5 . . ?
C2 C3 C4 121.1(3) . . ?
C2 C3 H3 119.5 . . ?
C14 C15 H15 119.2 . . ?
C16 C15 C14 121.7(3) . . ?
C16 C15 H15 119.2 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
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
O2 C31 1.256(4) . ?
O3 C32 1.262(4) . ?
O1 C31 1.250(3) . ?
O5 H5A 0.8705 . ?
O5 H5B 0.8698 . ?
O4 C32 1.250(4) . ?
O7 H7D 0.8699 . ?
O7 H7E 0.8700 . ?
O8 H8D 0.8697 . ?
O8 H8E 0.8690 . ?
O6 H6A 0.8701 . ?
O6 H6B 0.8699 . ?
O9 H9D 0.8702 . ?
O9 H9E 0.8703 . ?
N1 C1 1.500(4) . ?
N1 C9 1.509(4) . ?
N1 C8 1.503(4) . ?
N1 C7 1.511(4) . ?
N2 C11 1.499(4) . ?
N2 C19 1.506(4) . ?
N2 C17 1.510(4) . ?
N2 C18 1.502(4) . ?
C26 C25 1.446(4) . ?
C26 C21 1.430(4) . ?
C26 C27 1.435(4) . ?
C25 C30 1.438(4) . ?
C25 C24 1.427(4) . ?
C31 C21 1.519(4) . ?
C32 C27 1.523(4) . ?
C30 C24 1.473(4) 2_666 ?
C30 C29 1.376(4) . ?
C24 C23 1.389(4) . ?
C1 C6 1.387(4) . ?
C1 C2 1.385(4) . ?
C14 C4 1.483(4) . ?
C14 C13 1.394(4) . ?
C14 C15 1.400(4) . ?
C12 H12 0.9500 . ?
C12 C11 1.386(4) . ?
C12 C13 1.386(4) . ?
C21 C22 1.375(4) . ?
C4 C5 1.385(4) . ?
C4 C3 1.403(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.399(4) . ?
C23 H23 0.9500 . ?
C27 C28 1.377(4) . ?
C6 H6 0.9500 . ?
C6 C5 1.390(4) . ?
C28 H28 0.9500 . ?
C28 C29 1.394(4) . ?
C29 H29 0.9500 . ?
C5 H5 0.9500 . ?
C2 H2 0.9500 . ?
C2 C3 1.385(4) . ?
C11 C16 1.391(4) . ?
C13 H13 0.9500 . ?
C16 H16 0.9500 . ?
C16 C15 1.378(4) . ?
C3 H3 0.9500 . ?
C15 H15 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
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
O2 C31 C21 C26 -41.7(4) . . . . ?
O2 C31 C21 C22 132.2(3) . . . . ?
O3 C32 C27 C26 -50.1(4) . . . . ?
O3 C32 C27 C28 119.9(3) . . . . ?
O1 C31 C21 C26 143.4(3) . . . . ?
O1 C31 C21 C22 -42.6(4) . . . . ?
O4 C32 C27 C26 137.5(3) . . . . ?
O4 C32 C27 C28 -52.6(4) . . . . ?
N1 C1 C6 C5 179.5(3) . . . . ?
N1 C1 C2 C3 -179.0(3) . . . . ?
N2 C11 C16 C15 -179.0(3) . . . . ?
C26 C25 C30 C24 -179.9(2) . . . 2_666 ?
C26 C25 C30 C29 0.7(4) . . . . ?
C26 C25 C24 C30 179.9(2) . . . 2_666 ?
C26 C25 C24 C23 2.3(4) . . . . ?
C26 C21 C22 C23 4.5(4) . . . . ?
C26 C27 C28 C29 3.2(4) . . . . ?
C25 C26 C21 C31 168.6(3) . . . . ?
C25 C26 C21 C22 -5.2(4) . . . . ?
C25 C26 C27 C32 165.7(3) . . . . ?
C25 C26 C27 C28 -3.8(4) . . . . ?
C25 C30 C29 C28 -1.5(4) . . . . ?
C25 C24 C23 C22 -3.2(4) . . . . ?
C31 C21 C22 C23 -169.9(3) . . . . ?
C32 C27 C28 C29 -167.5(3) . . . . ?
C30 C25 C24 C30 1.1(4) . . . 2_666 ?
C30 C25 C24 C23 -176.5(3) . . . . ?
C30 C24 C23 C22 179.2(3) 2_666 . . . ?
C24 C25 C30 C24 -1.1(4) . . . 2_666 ?
C24 C25 C30 C29 179.5(3) . . . . ?
C24 C30 C29 C28 179.1(3) 2_666 . . . ?
C1 C6 C5 C4 -0.7(4) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C14 C4 C5 C6 -176.5(3) . . . . ?
C14 C4 C3 C2 176.9(3) . . . . ?
C12 C11 C16 C15 2.3(5) . . . . ?
C21 C26 C25 C30 -179.3(2) . . . . ?
C21 C26 C25 C24 1.9(4) . . . . ?
C21 C26 C27 C32 -13.1(5) . . . . ?
C21 C26 C27 C28 177.4(3) . . . . ?
C21 C22 C23 C24 -0.2(5) . . . . ?
C4 C14 C13 C12 -174.2(3) . . . . ?
C4 C14 C15 C16 174.5(3) . . . . ?
C27 C26 C25 C30 1.9(4) . . . . ?
C27 C26 C25 C24 -176.9(3) . . . . ?
C27 C26 C21 C31 -12.7(4) . . . . ?
C27 C26 C21 C22 173.6(3) . . . . ?
C27 C28 C29 C30 -0.5(5) . . . . ?
C6 C1 C2 C3 1.1(4) . . . . ?
C5 C4 C3 C2 -1.0(4) . . . . ?
C2 C1 C6 C5 -0.7(4) . . . . ?
C11 C12 C13 C14 -0.7(4) . . . . ?
C11 C16 C15 C14 -0.1(5) . . . . ?
C13 C14 C4 C5 143.4(3) . . . . ?
C13 C14 C4 C3 -34.5(4) . . . . ?
C13 C14 C15 C16 -2.4(4) . . . . ?
C13 C12 C11 N2 179.3(3) . . . . ?
C13 C12 C11 C16 -2.0(4) . . . . ?
C3 C4 C5 C6 1.5(4) . . . . ?
C15 C14 C4 C5 -33.5(4) . . . . ?
C15 C14 C4 C3 148.6(3) . . . . ?
C15 C14 C13 C12 2.8(4) . . . . ?
C9 N1 C1 C6 -127.1(3) . . . . ?
C9 N1 C1 C2 53.1(3) . . . . ?
C19 N2 C11 C12 -16.0(4) . . . . ?
C19 N2 C11 C16 165.3(3) . . . . ?
C8 N1 C1 C6 -6.9(4) . . . . ?
C8 N1 C1 C2 173.3(3) . . . . ?
C7 N1 C1 C6 113.6(3) . . . . ?
C7 N1 C1 C2 -66.3(3) . . . . ?
C17 N2 C11 C12 -135.9(3) . . . . ?
C17 N2 C11 C16 45.4(3) . . . . ?
C18 N2 C11 C12 103.9(3) . . . . ?
C18 N2 C11 C16 -74.9(3) . . . . ?
