#------------------------------------------------------------------------------
#$Date: 2024-12-06 17:29:58 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296320 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/36/7133653.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_7133653
loop_
_publ_author_name
'Juneja, Navkiran'
'Hastings, Josephine L.'
'Stoll, William B.'
'Brennessel, William W.'
'Zarrella, Salvatore'
'Sornberger, Parker'
'Catalano, Luca'
'Korter, Timothy M.'
'Ruggiero, Michael T.'
_publ_section_title
;
 Fundamentally intertwined: anharmonic intermolecular interactions dictate
 both thermal expansion and terahertz lattice dynamics in molecular
 crystals.
;
_journal_issue                   84
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12169
_journal_page_last               12172
_journal_paper_doi               10.1039/d4cc03307h
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C9 H6 O6, 2(C10 H8 N4)'
_chemical_formula_sum            'C29 H22 N8 O6'
_chemical_formula_weight         578.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-07-26
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-08-14 deposited with the CCDC.	2024-09-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.3440(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9549(2)
_cell_length_b                   12.38820(10)
_cell_length_c                   16.6141(2)
_cell_measurement_reflns_used    20818
_cell_measurement_temperature    110.02(10)
_cell_measurement_theta_max      79.4880
_cell_measurement_theta_min      3.5750
_cell_volume                     2693.02(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.101a (Rigaku OD, 2023)'
_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      110.02(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_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   -121.00 -34.00   0.50    0.28    --  -47.28 -24.00 178.00  174
  2  ω    -15.00  27.00   0.50    0.28    --  -47.28  24.00 -16.00   84
  3  ω     35.00 122.00   0.50    0.28    --   47.28  24.00 -16.00  174
  4  ω    -27.00  35.00   0.50    0.28    --   47.28 -24.00 178.00  124
  5  ω   -166.00 -78.00   0.50    1.10    --  -91.75 -24.00 178.00  176
  6  ω    101.00 178.00   0.50    1.10    --  113.25  24.00 -16.00  154
  7  ω    -31.00  26.00   0.50    0.28    --  -47.28  38.00 120.00  114
  8  ω    -10.00  28.00   0.50    0.28    --  -47.28  19.00  30.00   76
  9  ω    -31.00  26.00   0.50    0.28    --  -47.28  38.00 -60.00  114
 10  ω    -86.00 -13.00   0.50    0.28    --  -47.28 125.00-180.00  146
 11  ω    -63.00 -19.00   0.50    1.10    --  -91.75  61.00 150.00   88
 12  ω     42.00  83.00   0.50    1.10    --  113.25 -61.00-180.00   82
 13  ω     42.00  83.00   0.50    1.10    --  113.25 -61.00 -30.00   82
 14  ω     42.00  83.00   0.50    1.10    --  113.25 -61.00-150.00   82
 15  ω     42.00  83.00   0.50    1.10    --  113.25 -61.00 -60.00   82
 16  ω     44.00 111.00   0.50    1.10    --  113.25-125.00 120.00  134
 17  ω     41.00 178.00   0.50    1.10    --  113.25   0.00 120.00  274
 18  ω    101.00 178.00   0.50    1.10    --  113.25  30.00 -90.00  154
 19  ω     42.00  83.00   0.50    1.10    --  113.25 -61.00  30.00   82
 20  ω     42.00 106.00   0.50    1.10    --  113.25 -94.00 120.00  128
 21  ω     42.00  83.00   0.50    1.10    --  113.25 -61.00-120.00   82
 22  ω     44.00 111.00   0.50    1.10    --  113.25-125.00 120.00  134
 23  ω     42.00 106.00   0.50    1.10    --  113.25 -94.00  90.00  128
 24  ω     42.00  83.00   0.50    1.10    --  113.25 -61.00 150.00   82
 25  ω     42.00  83.00   0.50    1.10    --  113.25 -61.00 -90.00   82
 26  ω    101.00 178.00   0.50    1.10    --  113.25  30.00 -60.00  154
 27  ω     42.00 106.00   0.50    1.10    --  113.25 -94.00 -30.00  128
 28  ω     41.00 178.00   0.50    1.10    --  113.25   0.00 -60.00  274
 29  ω     42.00 102.00   0.50    1.10    --  113.25 -94.00-180.00  120
 30  ω     69.00  95.00   0.50    1.10    --  113.25 -94.00 -90.00   52
 31  ω     50.00  77.00   0.50    1.10    --  113.25 -61.00  60.00   54
 32  ω     50.00  83.00   0.50    1.10    --  113.25 -61.00   0.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1013162000
_diffrn_orient_matrix_UB_12      0.0066561000
_diffrn_orient_matrix_UB_13      0.0765576000
_diffrn_orient_matrix_UB_21      0.0549799000
_diffrn_orient_matrix_UB_22      0.0388483000
_diffrn_orient_matrix_UB_23      -0.0606406000
_diffrn_orient_matrix_UB_31      -0.0238386000
_diffrn_orient_matrix_UB_32      0.1179627000
_diffrn_orient_matrix_UB_33      0.0156586000
_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  0.0471
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            35109
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.223
_diffrn_reflns_theta_min         3.378
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.866
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.101a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1200
_exptl_crystal_recrystallization_method 'Crystals were grown from DMSO'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.354
_exptl_crystal_size_min          0.126
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         5808
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0490
_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)+(0.0802P)²+1.2259P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1376
_refine_ls_wR_factor_ref         0.1402
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5381
_reflns_number_total             5808
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc03307h3.cif
_cod_data_source_block           TMA_azo_2_110_00_auto
_cod_depositor_comments
'Adding full bibliography for 7133650--7133654.cif.'
_cod_database_code               7133653
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_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   0.899
_shelx_estimated_absorpt_t_min   0.723
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6A), C4(H4), C26(H26), C28(H28), C27(H27), C24(H24), C21(H21),
 C13(H13), C23(H23), C20(H20), C19(H19), C16(H16), C29(H29), C14(H14), C10(H10),
  C11(H11), C17(H17), C18(H18)
2.b Idealised tetrahedral OH refined as rotating group:
 O6(H6), O1(H1), O3(H3)
;
_olex2_exptl_crystal_mounting_method
'Crystal was mounted on a 100 um MiTeGen cryoloop'
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.353
_oxdiff_exptl_absorpt_empirical_full_min 0.727
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
O6 O 0.25044(8) 1.07062(8) 0.30864(7) 0.0284(2) Uani 1 1 d . . . . .
H6 H 0.260329 1.120809 0.278434 0.043 Uiso 1 1 calc R U . . .
O1 O 0.12965(9) 0.90833(8) 0.52188(7) 0.0297(2) Uani 1 1 d . . . . .
H1 H 0.106980 0.908612 0.562560 0.045 Uiso 1 1 calc R U . . .
O3 O 0.35921(9) 0.51833(8) 0.42258(8) 0.0307(3) Uani 1 1 d . . . . .
H3 H 0.395570 0.465386 0.419858 0.046 Uiso 1 1 calc R U . . .
O4 O 0.45477(9) 0.60546(8) 0.35929(8) 0.0342(3) Uani 1 1 d . . . . .
O2 O 0.15701(9) 0.73304(8) 0.55617(7) 0.0318(3) Uani 1 1 d . . . . .
O5 O 0.34277(10) 0.97498(9) 0.24718(8) 0.0384(3) Uani 1 1 d . . . . .
N8 N 0.70900(10) -0.26771(9) 0.27473(8) 0.0263(3) Uani 1 1 d . . . . .
N5 N 0.46322(10) 0.34847(10) 0.41090(8) 0.0271(3) Uani 1 1 d . . . . .
N2 N -0.04177(10) 0.90060(10) 0.86208(9) 0.0296(3) Uani 1 1 d . . . . .
N3 N -0.05254(10) 0.80954(10) 0.89021(8) 0.0278(3) Uani 1 1 d . . . . .
N1 N 0.07074(10) 0.91085(10) 0.65835(9) 0.0290(3) Uani 1 1 d . . . . .
N4 N -0.18542(11) 0.80767(11) 1.08288(9) 0.0339(3) Uani 1 1 d . . . . .
N6 N 0.61587(10) 0.08338(10) 0.35464(8) 0.0288(3) Uani 1 1 d . . . . .
N7 N 0.59467(10) -0.00750(10) 0.37524(9) 0.0295(3) Uani 1 1 d . . . . .
C1 C 0.22027(11) 0.80570(11) 0.45198(9) 0.0234(3) Uani 1 1 d . . . . .
C2 C 0.26790(11) 0.70896(11) 0.44495(9) 0.0236(3) Uani 1 1 d . . . . .
H2 H 0.259817 0.647039 0.475713 0.028 Uiso 1 1 calc R U . . .
C5 C 0.28527(11) 0.88854(11) 0.34967(9) 0.0243(3) Uani 1 1 d . . . . .
C7 C 0.16539(11) 0.81098(11) 0.51483(10) 0.0252(3) Uani 1 1 d . . . . .
C6 C 0.22926(11) 0.89565(11) 0.40452(9) 0.0237(3) Uani 1 1 d . . . . .
H6A H 0.197221 0.961692 0.409585 0.028 Uiso 1 1 calc R U . . .
C4 C 0.33540(11) 0.79281(11) 0.34540(9) 0.0246(3) Uani 1 1 d . . . . .
H4 H 0.375637 0.788650 0.309655 0.030 Uiso 1 1 calc R U . . .
C26 C 0.70613(12) -0.07704(11) 0.29695(10) 0.0275(3) Uani 1 1 d . . . . .
H26 H 0.728112 -0.006694 0.288592 0.033 Uiso 1 1 calc R U . . .
C3 C 0.32716(11) 0.70307(11) 0.39297(9) 0.0238(3) Uani 1 1 d . . . . .
C28 C 0.64780(12) -0.28233(11) 0.32007(10) 0.0273(3) Uani 1 1 d . . . . .
H28 H 0.627960 -0.353687 0.328236 0.033 Uiso 1 1 calc R U . . .
C12 C -0.00104(11) 0.89781(12) 0.79411(10) 0.0266(3) Uani 1 1 d . . . . .
C27 C 0.73796(12) -0.16683(11) 0.26380(10) 0.0266(3) Uani 1 1 d . . . . .
H27 H 0.782167 -0.156914 0.231955 0.032 Uiso 1 1 calc R U . . .
C22 C 0.56343(12) 0.16987(11) 0.37896(9) 0.0265(3) Uani 1 1 d . . . . .
C15 C -0.09639(11) 0.81450(12) 0.95646(10) 0.0263(3) Uani 1 1 d . . . . .
C8 C 0.38732(11) 0.60380(11) 0.38959(9) 0.0253(3) Uani 1 1 d . . . . .
C25 C 0.64057(11) -0.09292(11) 0.34318(10) 0.0263(3) Uani 1 1 d . . . . .
C9 C 0.29580(12) 0.98201(11) 0.29603(10) 0.0259(3) Uani 1 1 d . . . . .
C24 C 0.44287(12) 0.24906(12) 0.43304(10) 0.0281(3) Uani 1 1 d . . . . .
H24 H 0.392898 0.241407 0.459534 0.034 Uiso 1 1 calc R U . . .
C21 C 0.58544(12) 0.27244(12) 0.35643(10) 0.0281(3) Uani 1 1 d . . . . .
H21 H 0.634990 0.282594 0.329798 0.034 Uiso 1 1 calc R U . . .
C13 C 0.03834(13) 0.80672(12) 0.76764(10) 0.0299(3) Uani 1 1 d . . . . .
H13 H 0.041155 0.739183 0.795458 0.036 Uiso 1 1 calc R U . . .
C23 C 0.49148(12) 0.15723(12) 0.41899(10) 0.0284(3) Uani 1 1 d . . . . .
H23 H 0.476247 0.088030 0.436058 0.034 Uiso 1 1 calc R U . . .
C20 C 0.53350(12) 0.35948(12) 0.37368(10) 0.0276(3) Uani 1 1 d . . . . .
H20 H 0.548394 0.429799 0.358460 0.033 Uiso 1 1 calc R U . . .
C19 C -0.11389(12) 0.71655(12) 0.98935(10) 0.0291(3) Uani 1 1 d . . . . .
H19 H -0.095845 0.650398 0.969415 0.035 Uiso 1 1 calc R U . . .
C16 C -0.12406(13) 0.90989(12) 0.98718(11) 0.0316(3) Uani 1 1 d . . . . .
H16 H -0.113287 0.978210 0.965786 0.038 Uiso 1 1 calc R U . . .
C29 C 0.61200(12) -0.19671(12) 0.35581(10) 0.0276(3) Uani 1 1 d . . . . .
H29 H 0.568822 -0.209215 0.388216 0.033 Uiso 1 1 calc R U . . .
C14 C 0.07316(13) 0.81732(12) 0.69984(11) 0.0310(3) Uani 1 1 d . . . . .
H14 H 0.100194 0.755377 0.681598 0.037 Uiso 1 1 calc R U . . .
C10 C 0.03387(13) 0.99795(13) 0.68500(11) 0.0314(3) Uani 1 1 d . . . . .
H10 H 0.032084 1.064512 0.656116 0.038 Uiso 1 1 calc R U . . .
C11 C -0.00186(13) 0.99528(13) 0.75299(11) 0.0318(3) Uani 1 1 d . . . . .
H11 H -0.026447 1.058985 0.771073 0.038 Uiso 1 1 calc R U . . .
C17 C -0.16763(13) 0.90145(13) 1.04972(11) 0.0343(3) Uani 1 1 d . . . . .
H17 H -0.186397 0.966348 1.070872 0.041 Uiso 1 1 calc R U . . .
C18 C -0.15839(13) 0.71770(13) 1.05207(11) 0.0326(3) Uani 1 1 d . . . . .
H18 H -0.170360 0.650483 1.074434 0.039 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
C9 O6 H6 109.5 . . ?
C7 O1 H1 109.5 . . ?
C8 O3 H3 109.5 . . ?
C28 N8 C27 118.96(12) . . ?
C20 N5 C24 118.65(12) . . ?
N3 N2 C12 113.94(12) . . ?
N2 N3 C15 112.77(12) . . ?
C10 N1 C14 118.09(13) . . ?
C18 N4 C17 116.57(13) . . ?
N7 N6 C22 113.97(13) . . ?
N6 N7 C25 112.77(13) . . ?
C2 C1 C7 118.07(12) . . ?
C2 C1 C6 119.97(13) . . ?
C6 C1 C7 121.87(12) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.07(12) . . ?
C3 C2 H2 120.0 . . ?
C6 C5 C9 122.20(12) . . ?
C4 C5 C6 119.55(13) . . ?
C4 C5 C9 118.23(13) . . ?
O1 C7 C1 113.65(12) . . ?
O2 C7 O1 124.08(13) . . ?
O2 C7 C1 122.25(13) . . ?
C1 C6 H6A 120.0 . . ?
C5 C6 C1 119.99(12) . . ?
C5 C6 H6A 120.0 . . ?
C5 C4 H4 119.7 . . ?
C5 C4 C3 120.65(13) . . ?
C3 C4 H4 119.7 . . ?
C27 C26 H26 121.0 . . ?
C27 C26 C25 117.93(13) . . ?
C25 C26 H26 121.0 . . ?
C2 C3 C4 119.69(12) . . ?
C2 C3 C8 121.85(12) . . ?
C4 C3 C8 118.40(13) . . ?
N8 C28 H28 118.9 . . ?
N8 C28 C29 122.24(13) . . ?
C29 C28 H28 118.9 . . ?
C13 C12 N2 125.32(13) . . ?
C11 C12 N2 115.52(13) . . ?
C11 C12 C13 119.16(14) . . ?
N8 C27 C26 122.75(13) . . ?
N8 C27 H27 118.6 . . ?
C26 C27 H27 118.6 . . ?
C21 C22 N6 115.19(13) . . ?
C21 C22 C23 119.69(13) . . ?
C23 C22 N6 125.06(13) . . ?
C19 C15 N3 116.44(13) . . ?
C19 C15 C16 119.23(13) . . ?
C16 C15 N3 124.31(13) . . ?
O3 C8 C3 113.13(12) . . ?
O4 C8 O3 125.08(13) . . ?
O4 C8 C3 121.79(13) . . ?
C26 C25 N7 124.28(13) . . ?
C29 C25 N7 116.13(13) . . ?
C29 C25 C26 119.49(13) . . ?
O6 C9 C5 113.36(12) . . ?
O5 C9 O6 124.58(13) . . ?
O5 C9 C5 122.06(13) . . ?
N5 C24 H24 118.5 . . ?
N5 C24 C23 122.96(14) . . ?
C23 C24 H24 118.5 . . ?
C22 C21 H21 120.8 . . ?
C20 C21 C22 118.44(14) . . ?
C20 C21 H21 120.8 . . ?
C12 C13 H13 121.0 . . ?
C14 C13 C12 118.08(14) . . ?
C14 C13 H13 121.0 . . ?
C22 C23 H23 121.2 . . ?
C24 C23 C22 117.69(14) . . ?
C24 C23 H23 121.2 . . ?
N5 C20 C21 122.55(14) . . ?
N5 C20 H20 118.7 . . ?
C21 C20 H20 118.7 . . ?
C15 C19 H19 120.9 . . ?
C18 C19 C15 118.25(14) . . ?
C18 C19 H19 120.9 . . ?
C15 C16 H16 121.2 . . ?
C17 C16 C15 117.57(14) . . ?
C17 C16 H16 121.2 . . ?
C28 C29 H29 120.7 . . ?
C25 C29 C28 118.61(14) . . ?
C25 C29 H29 120.7 . . ?
N1 C14 C13 123.25(14) . . ?
N1 C14 H14 118.4 . . ?
C13 C14 H14 118.4 . . ?
N1 C10 H10 118.6 . . ?
N1 C10 C11 122.73(14) . . ?
C11 C10 H10 118.6 . . ?
C12 C11 H11 120.7 . . ?
C10 C11 C12 118.66(14) . . ?
C10 C11 H11 120.7 . . ?
N4 C17 C16 124.53(14) . . ?
N4 C17 H17 117.7 . . ?
C16 C17 H17 117.7 . . ?
N4 C18 C19 123.86(14) . . ?
N4 C18 H18 118.1 . . ?
C19 C18 H18 118.1 . . ?
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
O6 H6 0.8400 . ?
O6 C9 1.3198(17) . ?
O1 H1 0.8400 . ?
O1 C7 1.3257(17) . ?
O3 H3 0.8400 . ?
O3 C8 1.3134(17) . ?
O4 C8 1.2121(18) . ?
O2 C7 1.2139(18) . ?
O5 C9 1.2107(18) . ?
N8 C28 1.333(2) . ?
N8 C27 1.3451(18) . ?
N5 C24 1.3436(19) . ?
N5 C20 1.336(2) . ?
N2 N3 1.2501(18) . ?
N2 C12 1.4302(19) . ?
N3 C15 1.4345(18) . ?
N1 C14 1.343(2) . ?
N1 C10 1.335(2) . ?
N4 C17 1.345(2) . ?
N4 C18 1.334(2) . ?
N6 N7 1.2421(18) . ?
N6 C22 1.4328(18) . ?
N7 C25 1.4321(18) . ?
C1 C2 1.3949(19) . ?
C1 C7 1.4956(19) . ?
C1 C6 1.3956(19) . ?
C2 H2 0.9500 . ?
C2 C3 1.390(2) . ?
C5 C6 1.394(2) . ?
C5 C4 1.3913(19) . ?
C5 C9 1.4992(19) . ?
C6 H6A 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.3917(19) . ?
C26 H26 0.9500 . ?
C26 C27 1.381(2) . ?
C26 C25 1.398(2) . ?
C3 C8 1.5009(19) . ?
C28 H28 0.9500 . ?
C28 C29 1.391(2) . ?
C12 C13 1.392(2) . ?
C12 C11 1.385(2) . ?
C27 H27 0.9500 . ?
C22 C21 1.389(2) . ?
C22 C23 1.393(2) . ?
C15 C19 1.387(2) . ?
C15 C16 1.394(2) . ?
C25 C29 1.384(2) . ?
C24 H24 0.9500 . ?
C24 C23 1.385(2) . ?
C21 H21 0.9500 . ?
C21 C20 1.384(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.379(2) . ?
C23 H23 0.9500 . ?
C20 H20 0.9500 . ?
C19 H19 0.9500 . ?
C19 C18 1.386(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.378(2) . ?
C29 H29 0.9500 . ?
C14 H14 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.385(2) . ?
C11 H11 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
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
O6 H6 N8 0.84 1.77 2.6068(16) 173.7 2_665 yes
O1 H1 N1 0.84 1.83 2.6671(16) 174.3 . yes
O3 H3 N5 0.84 1.76 2.6015(16) 175.6 . 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
_geom_torsion_publ_flag
N8 C28 C29 C25 0.4(2) . . . . ?
N5 C24 C23 C22 -0.9(2) . . . . ?
N2 N3 C15 C19 178.06(14) . . . . ?
N2 N3 C15 C16 -0.3(2) . . . . ?
N2 C12 C13 C14 178.90(15) . . . . ?
N2 C12 C11 C10 -178.28(15) . . . . ?
N3 N2 C12 C13 -9.2(2) . . . . ?
N3 N2 C12 C11 171.01(14) . . . . ?
N3 C15 C19 C18 -178.52(14) . . . . ?
N3 C15 C16 C17 178.49(15) . . . . ?
N1 C10 C11 C12 -1.2(3) . . . . ?
N6 N7 C25 C26 2.8(2) . . . . ?
N6 N7 C25 C29 -173.50(14) . . . . ?
N6 C22 C21 C20 176.55(14) . . . . ?
N6 C22 C23 C24 -175.81(14) . . . . ?
N7 N6 C22 C21 -179.78(14) . . . . ?
N7 N6 C22 C23 -2.5(2) . . . . ?
N7 C25 C29 C28 174.95(14) . . . . ?
C1 C2 C3 C4 -2.6(2) . . . . ?
C1 C2 C3 C8 174.42(13) . . . . ?
C2 C1 C7 O1 174.92(13) . . . . ?
C2 C1 C7 O2 -3.7(2) . . . . ?
C2 C1 C6 C5 0.4(2) . . . . ?
C2 C3 C8 O3 15.5(2) . . . . ?
C2 C3 C8 O4 -164.25(15) . . . . ?
C5 C4 C3 C2 0.3(2) . . . . ?
C5 C4 C3 C8 -176.77(13) . . . . ?
C7 C1 C2 C3 -174.42(13) . . . . ?
C7 C1 C6 C5 176.91(13) . . . . ?
C6 C1 C2 C3 2.2(2) . . . . ?
C6 C1 C7 O1 -1.6(2) . . . . ?
C6 C1 C7 O2 179.79(15) . . . . ?
C6 C5 C4 C3 2.3(2) . . . . ?
C6 C5 C9 O6 2.3(2) . . . . ?
C6 C5 C9 O5 -178.49(15) . . . . ?
C4 C5 C6 C1 -2.7(2) . . . . ?
C4 C5 C9 O6 -176.19(13) . . . . ?
C4 C5 C9 O5 3.0(2) . . . . ?
C4 C3 C8 O3 -167.50(13) . . . . ?
C4 C3 C8 O4 12.8(2) . . . . ?
C26 C25 C29 C28 -1.5(2) . . . . ?
C28 N8 C27 C26 -0.7(2) . . . . ?
C12 N2 N3 C15 -178.21(12) . . . . ?
C12 C13 C14 N1 -0.1(3) . . . . ?
C27 N8 C28 C29 0.6(2) . . . . ?
C27 C26 C25 N7 -174.67(14) . . . . ?
C27 C26 C25 C29 1.5(2) . . . . ?
C22 N6 N7 C25 174.49(12) . . . . ?
C22 C21 C20 N5 -0.1(2) . . . . ?
C15 C19 C18 N4 -0.1(3) . . . . ?
C15 C16 C17 N4 -0.2(3) . . . . ?
C25 C26 C27 N8 -0.4(2) . . . . ?
C9 C5 C6 C1 178.86(13) . . . . ?
C9 C5 C4 C3 -179.16(13) . . . . ?
C24 N5 C20 C21 0.6(2) . . . . ?
C21 C22 C23 C24 1.3(2) . . . . ?
C13 C12 C11 C10 1.9(2) . . . . ?
C23 C22 C21 C20 -0.9(2) . . . . ?
C20 N5 C24 C23 0.0(2) . . . . ?
C19 C15 C16 C17 0.2(2) . . . . ?
C16 C15 C19 C18 -0.1(2) . . . . ?
C14 N1 C10 C11 -0.2(2) . . . . ?
C10 N1 C14 C13 0.9(2) . . . . ?
C11 C12 C13 C14 -1.3(2) . . . . ?
C17 N4 C18 C19 0.1(3) . . . . ?
C18 N4 C17 C16 0.0(3) . . . . ?
