#------------------------------------------------------------------------------
#$Date: 2024-12-06 17:29:58 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296320 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/36/7133652.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_7133652
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                 110.2190(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.97610(10)
_cell_length_b                   12.38620(10)
_cell_length_c                   16.6209(2)
_cell_measurement_reflns_used    21133
_cell_measurement_temperature    130.01(10)
_cell_measurement_theta_max      79.6260
_cell_measurement_theta_min      3.3550
_cell_volume                     2699.96(5)
_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      130.01(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 0.987
_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      0.1011568000
_diffrn_orient_matrix_UB_12      0.0067799000
_diffrn_orient_matrix_UB_13      0.0762440000
_diffrn_orient_matrix_UB_21      0.0547052000
_diffrn_orient_matrix_UB_22      0.0388685000
_diffrn_orient_matrix_UB_23      -0.0608317000
_diffrn_orient_matrix_UB_31      -0.0238444000
_diffrn_orient_matrix_UB_32      0.1179601000
_diffrn_orient_matrix_UB_33      0.0156733000
_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  0.0488
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_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            35393
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.253
_diffrn_reflns_theta_min         3.370
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.864
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62201
_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    1.423
_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         0.309
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         5818
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0461
_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)+(0.0752P)²+1.0445P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1303
_refine_ls_wR_factor_ref         0.1329
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5378
_reflns_number_total             5818
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc03307h3.cif
_cod_data_source_block           TMA_azo_3_130_00_auto
_cod_depositor_comments
'Adding full bibliography for 7133650--7133654.cif.'
_cod_original_cell_volume        2699.95(5)
_cod_database_code               7133652
_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   0.724
_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 1.396
_oxdiff_exptl_absorpt_empirical_full_min 0.740
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 0.25053(8) 1.07038(7) 0.30862(7) 0.0306(2) Uani 1 1 d . . . . .
H6 H 0.261844 1.121054 0.279530 0.046 Uiso 1 1 calc R U . . .
O1 O 0.12993(8) 0.90830(8) 0.52199(7) 0.0318(2) Uani 1 1 d . . . . .
H1 H 0.108097 0.908829 0.563156 0.048 Uiso 1 1 calc R U . . .
O3 O 0.35946(8) 0.51843(7) 0.42274(7) 0.0331(2) Uani 1 1 d . . . . .
H3 H 0.396444 0.465759 0.420746 0.050 Uiso 1 1 calc R U . . .
O4 O 0.45461(9) 0.60539(8) 0.35916(8) 0.0372(3) Uani 1 1 d . . . . .
O2 O 0.15721(9) 0.73304(8) 0.55624(7) 0.0346(2) Uani 1 1 d . . . . .
O5 O 0.34264(10) 0.97483(8) 0.24711(8) 0.0420(3) Uani 1 1 d . . . . .
N8 N 0.70896(9) -0.26776(9) 0.27475(8) 0.0279(2) Uani 1 1 d . . . . .
N5 N 0.46306(9) 0.34836(9) 0.41084(8) 0.0291(3) Uani 1 1 d . . . . .
N2 N -0.04178(10) 0.90074(10) 0.86204(8) 0.0317(3) Uani 1 1 d . . . . .
N3 N -0.05259(9) 0.80969(10) 0.89012(8) 0.0297(3) Uani 1 1 d . . . . .
N1 N 0.07066(10) 0.91085(10) 0.65836(8) 0.0312(3) Uani 1 1 d . . . . .
N4 N -0.18535(11) 0.80771(11) 1.08283(9) 0.0370(3) Uani 1 1 d . . . . .
N6 N 0.61574(10) 0.08327(10) 0.35464(8) 0.0313(3) Uani 1 1 d . . . . .
N7 N 0.59441(10) -0.00739(10) 0.37505(9) 0.0323(3) Uani 1 1 d . . . . .
C1 C 0.22056(10) 0.80567(10) 0.45205(9) 0.0247(3) Uani 1 1 d . . . . .
C2 C 0.26813(10) 0.70897(10) 0.44507(9) 0.0249(3) Uani 1 1 d . . . . .
H2 H 0.260100 0.647098 0.475908 0.030 Uiso 1 1 calc R U . . .
C5 C 0.28540(10) 0.88826(10) 0.34969(9) 0.0255(3) Uani 1 1 d . . . . .
C7 C 0.16565(11) 0.81094(11) 0.51490(9) 0.0266(3) Uani 1 1 d . . . . .
C6 C 0.22937(10) 0.89547(10) 0.40459(9) 0.0251(3) Uani 1 1 d . . . . .
H6A H 0.197283 0.961486 0.409596 0.030 Uiso 1 1 calc R U . . .
C4 C 0.33540(11) 0.79272(10) 0.34539(9) 0.0260(3) Uani 1 1 d . . . . .
H4 H 0.375529 0.788544 0.309566 0.031 Uiso 1 1 calc R U . . .
C26 C 0.70599(11) -0.07699(11) 0.29683(9) 0.0294(3) Uani 1 1 d . . . . .
H26 H 0.727881 -0.006629 0.288386 0.035 Uiso 1 1 calc R U . . .
C3 C 0.32729(10) 0.70301(10) 0.39305(9) 0.0249(3) Uani 1 1 d . . . . .
C28 C 0.64777(11) -0.28218(11) 0.32004(9) 0.0292(3) Uani 1 1 d . . . . .
H28 H 0.627964 -0.353519 0.328304 0.035 Uiso 1 1 calc R U . . .
C12 C -0.00106(11) 0.89795(11) 0.79403(9) 0.0284(3) Uani 1 1 d . . . . .
C27 C 0.73798(11) -0.16696(11) 0.26377(9) 0.0285(3) Uani 1 1 d . . . . .
H27 H 0.782273 -0.157130 0.232015 0.034 Uiso 1 1 calc R U . . .
C22 C 0.56324(11) 0.16975(11) 0.37893(9) 0.0283(3) Uani 1 1 d . . . . .
C15 C -0.09634(11) 0.81457(11) 0.95636(9) 0.0280(3) Uani 1 1 d . . . . .
C8 C 0.38730(11) 0.60375(10) 0.38960(9) 0.0267(3) Uani 1 1 d . . . . .
C25 C 0.64054(11) -0.09278(11) 0.34299(9) 0.0281(3) Uani 1 1 d . . . . .
C9 C 0.29583(11) 0.98191(10) 0.29600(9) 0.0276(3) Uani 1 1 d . . . . .
C24 C 0.44277(11) 0.24905(11) 0.43306(10) 0.0304(3) Uani 1 1 d . . . . .
H24 H 0.392874 0.241409 0.459604 0.037 Uiso 1 1 calc R U . . .
C21 C 0.58534(12) 0.27224(12) 0.35654(9) 0.0303(3) Uani 1 1 d . . . . .
H21 H 0.634967 0.282424 0.330029 0.036 Uiso 1 1 calc R U . . .
C13 C 0.03851(12) 0.80694(12) 0.76774(10) 0.0318(3) Uani 1 1 d . . . . .
H13 H 0.041556 0.739481 0.795715 0.038 Uiso 1 1 calc R U . . .
C23 C 0.49135(11) 0.15723(11) 0.41902(10) 0.0306(3) Uani 1 1 d . . . . .
H23 H 0.476150 0.088043 0.436148 0.037 Uiso 1 1 calc R U . . .
C20 C 0.53338(11) 0.35928(11) 0.37375(9) 0.0296(3) Uani 1 1 d . . . . .
H20 H 0.548338 0.429603 0.358567 0.036 Uiso 1 1 calc R U . . .
C19 C -0.11372(11) 0.71676(12) 0.98930(10) 0.0314(3) Uani 1 1 d . . . . .
H19 H -0.095577 0.650611 0.969437 0.038 Uiso 1 1 calc R U . . .
C16 C -0.12424(12) 0.90992(12) 0.98698(11) 0.0344(3) Uani 1 1 d . . . . .
H16 H -0.113722 0.978262 0.965452 0.041 Uiso 1 1 calc R U . . .
C29 C 0.61189(11) -0.19650(11) 0.35562(9) 0.0298(3) Uani 1 1 d . . . . .
H29 H 0.568617 -0.208931 0.387935 0.036 Uiso 1 1 calc R U . . .
C14 C 0.07325(12) 0.81749(12) 0.69982(10) 0.0333(3) Uani 1 1 d . . . . .
H14 H 0.100305 0.755561 0.681578 0.040 Uiso 1 1 calc R U . . .
C10 C 0.03371(12) 0.99785(12) 0.68491(10) 0.0335(3) Uani 1 1 d . . . . .
H10 H 0.031917 1.064377 0.655981 0.040 Uiso 1 1 calc R U . . .
C11 C -0.00214(13) 0.99530(12) 0.75282(11) 0.0339(3) Uani 1 1 d . . . . .
H11 H -0.026941 1.058986 0.770755 0.041 Uiso 1 1 calc R U . . .
C17 C -0.16764(13) 0.90145(13) 1.04963(11) 0.0376(3) Uani 1 1 d . . . . .
H17 H -0.186343 0.966352 1.070825 0.045 Uiso 1 1 calc R U . . .
C18 C -0.15825(12) 0.71785(13) 1.05198(10) 0.0352(3) Uani 1 1 d . . . . .
H18 H -0.170188 0.650578 1.074304 0.042 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 118.94(12) . . ?
C20 N5 C24 118.62(12) . . ?
N3 N2 C12 113.94(12) . . ?
N2 N3 C15 112.80(11) . . ?
C10 N1 C14 118.14(12) . . ?
C18 N4 C17 116.46(13) . . ?
N7 N6 C22 113.91(12) . . ?
N6 N7 C25 112.65(12) . . ?
C2 C1 C7 118.04(12) . . ?
C6 C1 C2 120.05(12) . . ?
C6 C1 C7 121.83(12) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.06(12) . . ?
C3 C2 H2 120.0 . . ?
C6 C5 C9 122.07(12) . . ?
C4 C5 C6 119.62(12) . . ?
C4 C5 C9 118.29(12) . . ?
O1 C7 C1 113.67(11) . . ?
O2 C7 O1 124.03(12) . . ?
O2 C7 C1 122.29(12) . . ?
C1 C6 C5 119.89(12) . . ?
C1 C6 H6A 120.1 . . ?
C5 C6 H6A 120.1 . . ?
C5 C4 H4 119.7 . . ?
C5 C4 C3 120.64(12) . . ?
C3 C4 H4 119.7 . . ?
C27 C26 H26 121.0 . . ?
C27 C26 C25 117.94(13) . . ?
C25 C26 H26 121.0 . . ?
C2 C3 C4 119.66(12) . . ?
C2 C3 C8 121.87(12) . . ?
C4 C3 C8 118.41(12) . . ?
N8 C28 H28 118.8 . . ?
N8 C28 C29 122.30(13) . . ?
C29 C28 H28 118.8 . . ?
C13 C12 N2 125.28(13) . . ?
C11 C12 N2 115.50(12) . . ?
C11 C12 C13 119.22(13) . . ?
N8 C27 C26 122.69(13) . . ?
N8 C27 H27 118.7 . . ?
C26 C27 H27 118.7 . . ?
C21 C22 N6 115.17(13) . . ?
C21 C22 C23 119.63(12) . . ?
C23 C22 N6 125.16(13) . . ?
C19 C15 N3 116.51(12) . . ?
C19 C15 C16 119.17(13) . . ?
C16 C15 N3 124.30(13) . . ?
O3 C8 C3 113.16(11) . . ?
O4 C8 O3 125.06(12) . . ?
O4 C8 C3 121.78(12) . . ?
C26 C25 N7 124.41(13) . . ?
C29 C25 N7 115.97(13) . . ?
C29 C25 C26 119.51(12) . . ?
O6 C9 C5 113.40(12) . . ?
O5 C9 O6 124.62(12) . . ?
O5 C9 C5 121.97(12) . . ?
N5 C24 H24 118.5 . . ?
N5 C24 C23 122.92(14) . . ?
C23 C24 H24 118.5 . . ?
C22 C21 H21 120.8 . . ?
C20 C21 C22 118.43(13) . . ?
C20 C21 H21 120.8 . . ?
C12 C13 H13 121.0 . . ?
C14 C13 C12 118.07(13) . . ?
C14 C13 H13 121.0 . . ?
C22 C23 H23 121.1 . . ?
C24 C23 C22 117.77(13) . . ?
C24 C23 H23 121.1 . . ?
N5 C20 C21 122.62(13) . . ?
N5 C20 H20 118.7 . . ?
C21 C20 H20 118.7 . . ?
C15 C19 H19 120.8 . . ?
C15 C19 C18 118.31(13) . . ?
C18 C19 H19 120.8 . . ?
C15 C16 H16 121.2 . . ?
C17 C16 C15 117.58(13) . . ?
C17 C16 H16 121.2 . . ?
C28 C29 H29 120.7 . . ?
C25 C29 C28 118.60(13) . . ?
C25 C29 H29 120.7 . . ?
N1 C14 C13 123.19(13) . . ?
N1 C14 H14 118.4 . . ?
C13 C14 H14 118.4 . . ?
N1 C10 H10 118.6 . . ?
N1 C10 C11 122.80(13) . . ?
C11 C10 H10 118.6 . . ?
C12 C11 C10 118.55(13) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
N4 C17 C16 124.57(14) . . ?
N4 C17 H17 117.7 . . ?
C16 C17 H17 117.7 . . ?
N4 C18 C19 123.91(14) . . ?
N4 C18 H18 118.0 . . ?
C19 C18 H18 118.0 . . ?
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 1.3180(16) . ?
O1 H1 0.8400 . ?
O1 C7 1.3259(16) . ?
O3 H3 0.8400 . ?
O3 C8 1.3114(16) . ?
O4 C8 1.2125(17) . ?
O2 C7 1.2137(17) . ?
O5 C9 1.2098(18) . ?
N8 C28 1.3322(19) . ?
N8 C27 1.3445(18) . ?
N5 C24 1.3426(18) . ?
N5 C20 1.3353(19) . ?
N2 N3 1.2494(17) . ?
N2 C12 1.4310(18) . ?
N3 C15 1.4335(17) . ?
N1 C14 1.3401(19) . ?
N1 C10 1.3342(19) . ?
N4 C17 1.345(2) . ?
N4 C18 1.334(2) . ?
N6 N7 1.2389(18) . ?
N6 C22 1.4330(17) . ?
N7 C25 1.4337(17) . ?
C1 C2 1.3940(18) . ?
C1 C7 1.4964(18) . ?
C1 C6 1.3934(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.3895(18) . ?
C5 C6 1.3956(19) . ?
C5 C4 1.3887(18) . ?
C5 C9 1.5009(18) . ?
C6 H6A 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.3918(18) . ?
C26 H26 0.9500 . ?
C26 C27 1.3834(19) . ?
C26 C25 1.396(2) . ?
C3 C8 1.5006(17) . ?
C28 H28 0.9500 . ?
C28 C29 1.3901(19) . ?
C12 C13 1.391(2) . ?
C12 C11 1.384(2) . ?
C27 H27 0.9500 . ?
C22 C21 1.387(2) . ?
C22 C23 1.393(2) . ?
C15 C19 1.385(2) . ?
C15 C16 1.394(2) . ?
C25 C29 1.383(2) . ?
C24 H24 0.9500 . ?
C24 C23 1.3850(19) . ?
C21 H21 0.9500 . ?
C21 C20 1.3838(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.381(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 2.6082(15) 175.9 2_665 yes
O1 H1 N1 0.84 1.83 2.6688(16) 175.6 . yes
O3 H3 N5 0.84 1.76 2.6021(15) 174.4 . 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 0.3(2) . . . . ?
N5 C24 C23 C22 -0.9(2) . . . . ?
N2 N3 C15 C19 178.16(13) . . . . ?
N2 N3 C15 C16 0.0(2) . . . . ?
N2 C12 C13 C14 178.86(14) . . . . ?
N2 C12 C11 C10 -178.36(14) . . . . ?
N3 N2 C12 C13 -9.4(2) . . . . ?
N3 N2 C12 C11 170.79(14) . . . . ?
N3 C15 C19 C18 -178.45(14) . . . . ?
N3 C15 C16 C17 178.54(15) . . . . ?
N1 C10 C11 C12 -1.1(2) . . . . ?
N6 N7 C25 C26 2.6(2) . . . . ?
N6 N7 C25 C29 -173.61(13) . . . . ?
N6 C22 C21 C20 176.55(13) . . . . ?
N6 C22 C23 C24 -175.85(14) . . . . ?
N7 N6 C22 C21 -179.73(13) . . . . ?
N7 N6 C22 C23 -2.3(2) . . . . ?
N7 C25 C29 C28 174.98(13) . . . . ?
C1 C2 C3 C4 -2.6(2) . . . . ?
C1 C2 C3 C8 174.50(13) . . . . ?
C2 C1 C7 O1 174.88(12) . . . . ?
C2 C1 C7 O2 -3.7(2) . . . . ?
C2 C1 C6 C5 0.4(2) . . . . ?
C2 C3 C8 O3 15.35(19) . . . . ?
C2 C3 C8 O4 -164.28(14) . . . . ?
C5 C4 C3 C2 0.4(2) . . . . ?
C5 C4 C3 C8 -176.82(13) . . . . ?
C7 C1 C2 C3 -174.50(12) . . . . ?
C7 C1 C6 C5 176.95(12) . . . . ?
C6 C1 C2 C3 2.2(2) . . . . ?
C6 C1 C7 O1 -1.77(19) . . . . ?
C6 C1 C7 O2 179.67(14) . . . . ?
C6 C5 C4 C3 2.2(2) . . . . ?
C6 C5 C9 O6 2.3(2) . . . . ?
C6 C5 C9 O5 -178.41(15) . . . . ?
C4 C5 C6 C1 -2.6(2) . . . . ?
C4 C5 C9 O6 -176.19(13) . . . . ?
C4 C5 C9 O5 3.1(2) . . . . ?
C4 C3 C8 O3 -167.54(13) . . . . ?
C4 C3 C8 O4 12.8(2) . . . . ?
C26 C25 C29 C28 -1.4(2) . . . . ?
C28 N8 C27 C26 -0.7(2) . . . . ?
C12 N2 N3 C15 -178.22(12) . . . . ?
C12 C13 C14 N1 0.1(2) . . . . ?
C27 N8 C28 C29 0.7(2) . . . . ?
C27 C26 C25 N7 -174.67(13) . . . . ?
C27 C26 C25 C29 1.4(2) . . . . ?
C22 N6 N7 C25 174.52(12) . . . . ?
C22 C21 C20 N5 -0.1(2) . . . . ?
C15 C19 C18 N4 -0.1(2) . . . . ?
C15 C16 C17 N4 -0.4(3) . . . . ?
C25 C26 C27 N8 -0.3(2) . . . . ?
C9 C5 C6 C1 178.93(13) . . . . ?
C9 C5 C4 C3 -179.23(13) . . . . ?
C24 N5 C20 C21 0.7(2) . . . . ?
C21 C22 C23 C24 1.5(2) . . . . ?
C13 C12 C11 C10 1.9(2) . . . . ?
C23 C22 C21 C20 -1.1(2) . . . . ?
C20 N5 C24 C23 -0.2(2) . . . . ?
C19 C15 C16 C17 0.4(2) . . . . ?
C16 C15 C19 C18 -0.2(2) . . . . ?
C14 N1 C10 C11 -0.3(2) . . . . ?
C10 N1 C14 C13 0.8(2) . . . . ?
C11 C12 C13 C14 -1.4(2) . . . . ?
C17 N4 C18 C19 0.2(2) . . . . ?
C18 N4 C17 C16 0.1(3) . . . . ?
