#------------------------------------------------------------------------------
#$Date: 2024-12-06 17:29:58 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296320 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/36/7133650.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_7133650
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             2024-07-24
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-08-14 deposited with the CCDC.	2024-09-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.4010(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9468(2)
_cell_length_b                   12.38920(10)
_cell_length_c                   16.6087(2)
_cell_measurement_reflns_used    20645
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.7590
_cell_measurement_theta_min      3.5820
_cell_volume                     2689.81(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 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 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      0.1013959000
_diffrn_orient_matrix_UB_12      0.0066030000
_diffrn_orient_matrix_UB_13      0.0766955000
_diffrn_orient_matrix_UB_21      0.0550872000
_diffrn_orient_matrix_UB_22      0.0388496000
_diffrn_orient_matrix_UB_23      -0.0605667000
_diffrn_orient_matrix_UB_31      -0.0238327000
_diffrn_orient_matrix_UB_32      0.1179628000
_diffrn_orient_matrix_UB_33      0.0156483000
_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  0.0526
_diffrn_reflns_av_unetI/netI     0.0311
_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            34952
_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         80.121
_diffrn_reflns_theta_min         3.381
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.867
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.458
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.101a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
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    1.429
_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         0.374
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         5799
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0494
_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)+(0.0829P)²+1.2251P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1447
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5352
_reflns_number_total             5799
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc03307h3.cif
_cod_data_source_block           TMA_azo_1_100_00_auto
_cod_depositor_comments
'Adding full bibliography for 7133650--7133654.cif.'
_cod_original_cell_volume        2689.80(6)
_cod_database_code               7133650
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C116  H100  N32  O24  '
_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 1.817
_oxdiff_exptl_absorpt_empirical_full_min 0.692
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 0.25049(9) 1.07073(8) 0.30863(7) 0.0280(2) Uani 1 1 d . . . . .
H6 H 0.261855 1.121495 0.279644 0.042 Uiso 1 1 calc R U . . .
O1 O 0.12961(9) 0.90843(8) 0.52185(7) 0.0291(3) Uani 1 1 d . . . . .
H1 H 0.105642 0.908236 0.561756 0.044 Uiso 1 1 calc R U . . .
O3 O 0.35910(9) 0.51830(8) 0.42254(8) 0.0299(3) Uani 1 1 d . . . . .
H3 H 0.395240 0.465203 0.419691 0.045 Uiso 1 1 calc R U . . .
O4 O 0.45481(9) 0.60546(9) 0.35934(8) 0.0334(3) Uani 1 1 d . . . . .
O2 O 0.15700(9) 0.73306(9) 0.55616(8) 0.0311(3) Uani 1 1 d . . . . .
O5 O 0.34297(11) 0.97509(9) 0.24723(8) 0.0374(3) Uani 1 1 d . . . . .
N8 N 0.70892(10) -0.26765(10) 0.27473(9) 0.0260(3) Uani 1 1 d . . . . .
N5 N 0.46315(10) 0.34852(10) 0.41087(8) 0.0268(3) Uani 1 1 d . . . . .
N2 N -0.04172(11) 0.90057(10) 0.86216(9) 0.0294(3) Uani 1 1 d . . . . .
N3 N -0.05250(10) 0.80946(10) 0.89018(9) 0.0275(3) Uani 1 1 d . . . . .
N1 N 0.07073(10) 0.91086(11) 0.65828(9) 0.0286(3) Uani 1 1 d . . . . .
N4 N -0.18553(11) 0.80759(11) 1.08289(10) 0.0330(3) Uani 1 1 d . . . . .
N6 N 0.61593(10) 0.08346(10) 0.35466(9) 0.0284(3) Uani 1 1 d . . . . .
N7 N 0.59466(11) -0.00746(10) 0.37548(9) 0.0291(3) Uani 1 1 d . . . . .
C1 C 0.22016(11) 0.80574(11) 0.45188(10) 0.0233(3) Uani 1 1 d . . . . .
C2 C 0.26779(11) 0.70906(11) 0.44479(10) 0.0238(3) Uani 1 1 d . . . . .
H2 H 0.259607 0.647110 0.475485 0.029 Uiso 1 1 calc R U . . .
C5 C 0.28520(11) 0.88864(11) 0.34968(10) 0.0245(3) Uani 1 1 d . . . . .
C7 C 0.16541(11) 0.81101(11) 0.51472(10) 0.0251(3) Uani 1 1 d . . . . .
C6 C 0.22928(11) 0.89568(11) 0.40447(10) 0.0238(3) Uani 1 1 d . . . . .
H6A H 0.197312 0.961755 0.409589 0.029 Uiso 1 1 calc R U . . .
C4 C 0.33545(11) 0.79289(11) 0.34532(10) 0.0244(3) Uani 1 1 d . . . . .
H4 H 0.375699 0.788764 0.309573 0.029 Uiso 1 1 calc R U . . .
C26 C 0.70610(12) -0.07700(12) 0.29705(10) 0.0270(3) Uani 1 1 d . . . . .
H26 H 0.728019 -0.006626 0.288685 0.032 Uiso 1 1 calc R U . . .
C3 C 0.32717(11) 0.70312(11) 0.39295(10) 0.0237(3) Uani 1 1 d . . . . .
C28 C 0.64776(12) -0.28212(12) 0.31999(10) 0.0271(3) Uani 1 1 d . . . . .
H28 H 0.627810 -0.353451 0.328063 0.032 Uiso 1 1 calc R U . . .
C12 C -0.00104(12) 0.89766(12) 0.79405(10) 0.0267(3) Uani 1 1 d . . . . .
C27 C 0.73812(12) -0.16674(12) 0.26377(10) 0.0262(3) Uani 1 1 d . . . . .
H27 H 0.782387 -0.156822 0.231975 0.031 Uiso 1 1 calc R U . . .
C22 C 0.56340(12) 0.16985(12) 0.37905(10) 0.0264(3) Uani 1 1 d . . . . .
C15 C -0.09629(12) 0.81440(12) 0.95654(10) 0.0261(3) Uani 1 1 d . . . . .
C8 C 0.38738(12) 0.60376(11) 0.38939(10) 0.0249(3) Uani 1 1 d . . . . .
C25 C 0.64067(12) -0.09276(12) 0.34327(10) 0.0262(3) Uani 1 1 d . . . . .
C9 C 0.29593(12) 0.98225(11) 0.29593(10) 0.0258(3) Uani 1 1 d . . . . .
C24 C 0.44284(12) 0.24908(12) 0.43320(10) 0.0277(3) Uani 1 1 d . . . . .
H24 H 0.392999 0.241449 0.459852 0.033 Uiso 1 1 calc R U . . .
C21 C 0.58544(12) 0.27249(12) 0.35644(10) 0.0279(3) Uani 1 1 d . . . . .
H21 H 0.634971 0.282687 0.329779 0.034 Uiso 1 1 calc R U . . .
C13 C 0.03836(13) 0.80658(12) 0.76759(11) 0.0294(3) Uani 1 1 d . . . . .
H13 H 0.041198 0.739062 0.795445 0.035 Uiso 1 1 calc R U . . .
C23 C 0.49144(12) 0.15728(12) 0.41904(10) 0.0281(3) Uani 1 1 d . . . . .
H23 H 0.476167 0.088072 0.436054 0.034 Uiso 1 1 calc R U . . .
C20 C 0.53339(12) 0.35942(12) 0.37378(10) 0.0273(3) Uani 1 1 d . . . . .
H20 H 0.548315 0.429755 0.358623 0.033 Uiso 1 1 calc R U . . .
C19 C -0.11383(12) 0.71652(12) 0.98940(10) 0.0286(3) Uani 1 1 d . . . . .
H19 H -0.095783 0.650371 0.969476 0.034 Uiso 1 1 calc R U . . .
C16 C -0.12410(13) 0.90978(13) 0.98724(11) 0.0311(3) Uani 1 1 d . . . . .
H16 H -0.113378 0.978090 0.965805 0.037 Uiso 1 1 calc R U . . .
C29 C 0.61205(12) -0.19666(12) 0.35586(10) 0.0273(3) Uani 1 1 d . . . . .
H29 H 0.568930 -0.209233 0.388318 0.033 Uiso 1 1 calc R U . . .
C14 C 0.07319(13) 0.81713(13) 0.69972(11) 0.0303(3) Uani 1 1 d . . . . .
H14 H 0.100195 0.755201 0.681435 0.036 Uiso 1 1 calc R U . . .
C10 C 0.03389(13) 0.99791(13) 0.68505(11) 0.0307(3) Uani 1 1 d . . . . .
H10 H 0.032150 1.064493 0.656202 0.037 Uiso 1 1 calc R U . . .
C11 C -0.00189(13) 0.99528(13) 0.75305(11) 0.0312(3) Uani 1 1 d . . . . .
H11 H -0.026457 1.058963 0.771181 0.037 Uiso 1 1 calc R U . . .
C17 C -0.16769(14) 0.90146(13) 1.04976(12) 0.0333(4) Uani 1 1 d . . . . .
H17 H -0.186428 0.966360 1.070930 0.040 Uiso 1 1 calc R U . . .
C18 C -0.15845(13) 0.71766(13) 1.05216(11) 0.0321(3) Uani 1 1 d . . . . .
H18 H -0.170401 0.650453 1.074549 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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.1880
1 -2 -1 0.1829
2 -1 -2 0.1496
8 -2 -8 0.1364
6 6 -5 0.1844
2 8 -1 0.1469
-8 0 8 0.1782
-7 -4 7 0.1976
1 -8 0 0.1836
5 5 -8 0.2132
6 -2 -9 0.1564
-7 0 10 0.1872
5 -5 -8 0.1861
-6 1 10 0.1911
-4 -4 9 0.2175
1 -8 1 0.1852
4 -2 -10 0.1852
0 7 -4 0.1867
-3 -2 10 0.1791
-4 0 11 0.1967
6 -6 0 0.1143
7 0 3 0.0459
-7 0 -3 0.0993
-7 2 -3 0.0959
-6 6 0 0.1629
-8 -3 -1 0.1107
-8 0 0 0.0819
7 4 1 0.0906
8 2 1 0.0641
8 -2 -1 0.0457
-7 -2 -3 0.1024
-8 1 -2 0.0752
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 119.00(12) . . ?
C20 N5 C24 118.65(13) . . ?
N3 N2 C12 113.80(12) . . ?
N2 N3 C15 112.70(12) . . ?
C10 N1 C14 118.12(13) . . ?
C18 N4 C17 116.61(14) . . ?
N7 N6 C22 113.75(13) . . ?
N6 N7 C25 112.50(13) . . ?
C2 C1 C7 118.10(13) . . ?
C2 C1 C6 119.90(13) . . ?
C6 C1 C7 121.90(13) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.15(13) . . ?
C3 C2 H2 119.9 . . ?
C6 C5 C9 122.30(13) . . ?
C4 C5 C6 119.61(13) . . ?
C4 C5 C9 118.07(13) . . ?
O1 C7 C1 113.69(12) . . ?
O2 C7 O1 123.97(14) . . ?
O2 C7 C1 122.33(13) . . ?
C1 C6 H6A 120.0 . . ?
C5 C6 C1 120.04(13) . . ?
C5 C6 H6A 120.0 . . ?
C5 C4 H4 119.7 . . ?
C5 C4 C3 120.52(13) . . ?
C3 C4 H4 119.7 . . ?
C27 C26 H26 120.9 . . ?
C27 C26 C25 118.12(13) . . ?
C25 C26 H26 120.9 . . ?
C2 C3 C4 119.68(13) . . ?
C2 C3 C8 121.99(13) . . ?
C4 C3 C8 118.27(13) . . ?
N8 C28 H28 118.8 . . ?
N8 C28 C29 122.38(13) . . ?
C29 C28 H28 118.8 . . ?
C13 C12 N2 125.36(14) . . ?
C11 C12 N2 115.36(13) . . ?
C11 C12 C13 119.29(14) . . ?
N8 C27 C26 122.50(14) . . ?
N8 C27 H27 118.8 . . ?
C26 C27 H27 118.8 . . ?
C21 C22 N6 115.07(13) . . ?
C21 C22 C23 119.69(13) . . ?
C23 C22 N6 125.18(13) . . ?
C19 C15 N3 116.47(13) . . ?
C19 C15 C16 119.18(14) . . ?
C16 C15 N3 124.33(13) . . ?
O3 C8 C3 112.93(12) . . ?
O4 C8 O3 125.21(13) . . ?
O4 C8 C3 121.86(13) . . ?
C26 C25 N7 124.45(13) . . ?
C29 C25 N7 116.03(13) . . ?
C29 C25 C26 119.41(13) . . ?
O6 C9 C5 113.17(12) . . ?
O5 C9 O6 124.79(13) . . ?
O5 C9 C5 122.03(13) . . ?
N5 C24 H24 118.6 . . ?
N5 C24 C23 122.86(14) . . ?
C23 C24 H24 118.6 . . ?
C22 C21 H21 120.8 . . ?
C20 C21 C22 118.30(14) . . ?
C20 C21 H21 120.8 . . ?
C12 C13 H13 120.9 . . ?
C14 C13 C12 118.11(14) . . ?
C14 C13 H13 120.9 . . ?
C22 C23 H23 121.1 . . ?
C24 C23 C22 117.78(14) . . ?
C24 C23 H23 121.1 . . ?
N5 C20 C21 122.71(14) . . ?
N5 C20 H20 118.6 . . ?
C21 C20 H20 118.6 . . ?
C15 C19 H19 120.9 . . ?
C15 C19 C18 118.27(14) . . ?
C18 C19 H19 120.9 . . ?
C15 C16 H16 121.2 . . ?
C17 C16 C15 117.66(14) . . ?
C17 C16 H16 121.2 . . ?
C28 C29 H29 120.7 . . ?
C25 C29 C28 118.57(14) . . ?
C25 C29 H29 120.7 . . ?
N1 C14 C13 123.12(14) . . ?
N1 C14 H14 118.4 . . ?
C13 C14 H14 118.4 . . ?
N1 C10 H10 118.6 . . ?
N1 C10 C11 122.83(14) . . ?
C11 C10 H10 118.6 . . ?
C12 C11 H11 120.7 . . ?
C10 C11 C12 118.51(14) . . ?
C10 C11 H11 120.7 . . ?
N4 C17 C16 124.44(15) . . ?
N4 C17 H17 117.8 . . ?
C16 C17 H17 117.8 . . ?
N4 C18 C19 123.83(15) . . ?
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 1.3194(17) . ?
O1 H1 0.8400 . ?
O1 C7 1.3271(17) . ?
O3 H3 0.8400 . ?
O3 C8 1.3157(17) . ?
O4 C8 1.2088(19) . ?
O2 C7 1.2151(18) . ?
O5 C9 1.2094(19) . ?
N8 C28 1.331(2) . ?
N8 C27 1.3466(19) . ?
N5 C24 1.3449(19) . ?
N5 C20 1.334(2) . ?
N2 N3 1.2498(18) . ?
N2 C12 1.4320(19) . ?
N3 C15 1.4356(19) . ?
N1 C14 1.344(2) . ?
N1 C10 1.336(2) . ?
N4 C17 1.346(2) . ?
N4 C18 1.334(2) . ?
N6 N7 1.2442(19) . ?
N6 C22 1.4330(18) . ?
N7 C25 1.4331(18) . ?
C1 C2 1.3943(19) . ?
C1 C7 1.494(2) . ?
C1 C6 1.396(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.389(2) . ?
C5 C6 1.392(2) . ?
C5 C4 1.3925(19) . ?
C5 C9 1.5024(19) . ?
C6 H6A 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.393(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.383(2) . ?
C26 C25 1.396(2) . ?
C3 C8 1.5028(19) . ?
C28 H28 0.9500 . ?
C28 C29 1.390(2) . ?
C12 C13 1.392(2) . ?
C12 C11 1.386(2) . ?
C27 H27 0.9500 . ?
C22 C21 1.390(2) . ?
C22 C23 1.392(2) . ?
C15 C19 1.386(2) . ?
C15 C16 1.395(2) . ?
C25 C29 1.385(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 1.380(2) . ?
C23 H23 0.9500 . ?
C20 H20 0.9500 . ?
C19 H19 0.9500 . ?
C19 C18 1.388(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 2.6064(16) 176.1 2_665 yes
O1 H1 N1 0.84 1.83 2.6660(17) 172.4 . yes
O3 H3 N5 0.84 1.76 2.6007(16) 176.0 . 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 0.5(2) . . . . ?
N5 C24 C23 C22 -0.7(2) . . . . ?
N2 N3 C15 C19 178.07(14) . . . . ?
N2 N3 C15 C16 -0.1(2) . . . . ?
N2 C12 C13 C14 178.97(15) . . . . ?
N2 C12 C11 C10 -178.37(15) . . . . ?
N3 N2 C12 C13 -9.3(2) . . . . ?
N3 N2 C12 C11 171.02(15) . . . . ?
N3 C15 C19 C18 -178.42(14) . . . . ?
N3 C15 C16 C17 178.41(15) . . . . ?
N1 C10 C11 C12 -1.2(3) . . . . ?
N6 N7 C25 C26 2.8(2) . . . . ?
N6 N7 C25 C29 -173.41(14) . . . . ?
N6 C22 C21 C20 176.56(14) . . . . ?
N6 C22 C23 C24 -175.86(15) . . . . ?
N7 N6 C22 C21 -179.85(14) . . . . ?
N7 N6 C22 C23 -2.6(2) . . . . ?
N7 C25 C29 C28 174.90(14) . . . . ?
C1 C2 C3 C4 -2.7(2) . . . . ?
C1 C2 C3 C8 174.48(14) . . . . ?
C2 C1 C7 O1 174.92(13) . . . . ?
C2 C1 C7 O2 -3.7(2) . . . . ?
C2 C1 C6 C5 0.5(2) . . . . ?
C2 C3 C8 O3 15.3(2) . . . . ?
C2 C3 C8 O4 -164.18(15) . . . . ?
C5 C4 C3 C2 0.4(2) . . . . ?
C5 C4 C3 C8 -176.85(14) . . . . ?
C7 C1 C2 C3 -174.29(13) . . . . ?
C7 C1 C6 C5 176.87(14) . . . . ?
C6 C1 C2 C3 2.2(2) . . . . ?
C6 C1 C7 O1 -1.5(2) . . . . ?
C6 C1 C7 O2 179.89(15) . . . . ?
C6 C5 C4 C3 2.3(2) . . . . ?
C6 C5 C9 O6 2.2(2) . . . . ?
C6 C5 C9 O5 -178.57(16) . . . . ?
C4 C5 C6 C1 -2.7(2) . . . . ?
C4 C5 C9 O6 -176.20(14) . . . . ?
C4 C5 C9 O5 3.0(2) . . . . ?
C4 C3 C8 O3 -167.55(14) . . . . ?
C4 C3 C8 O4 13.0(2) . . . . ?
C26 C25 C29 C28 -1.5(2) . . . . ?
C28 N8 C27 C26 -0.7(2) . . . . ?
C12 N2 N3 C15 -178.20(13) . . . . ?
C12 C13 C14 N1 0.0(3) . . . . ?
C27 N8 C28 C29 0.6(2) . . . . ?
C27 C26 C25 N7 -174.70(15) . . . . ?
C27 C26 C25 C29 1.4(2) . . . . ?
C22 N6 N7 C25 174.48(13) . . . . ?
C22 C21 C20 N5 -0.2(2) . . . . ?
C15 C19 C18 N4 0.0(3) . . . . ?
C15 C16 C17 N4 -0.3(3) . . . . ?
C25 C26 C27 N8 -0.3(2) . . . . ?
C9 C5 C6 C1 178.85(14) . . . . ?
C9 C5 C4 C3 -179.22(14) . . . . ?
C24 N5 C20 C21 0.7(2) . . . . ?
C21 C22 C23 C24 1.2(2) . . . . ?
C13 C12 C11 C10 2.0(2) . . . . ?
C23 C22 C21 C20 -0.8(2) . . . . ?
C20 N5 C24 C23 -0.3(2) . . . . ?
C19 C15 C16 C17 0.3(2) . . . . ?
C16 C15 C19 C18 -0.2(2) . . . . ?
C14 N1 C10 C11 -0.2(3) . . . . ?
C10 N1 C14 C13 0.8(3) . . . . ?
C11 C12 C13 C14 -1.4(2) . . . . ?
C17 N4 C18 C19 0.1(3) . . . . ?
C18 N4 C17 C16 0.1(3) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0003 -0.9993 0.0002 -0.0066 -0.0388 -0.1179
0.9999 -1.9987 -0.9977 0.0117 0.0379 -0.2752
1.9990 -0.9996 -1.9960 0.0430 0.1922 -0.1968
7.9328 -1.6333 -7.7128 0.2020 0.8407 -0.5024
5.7982 5.6842 -5.4438 0.2079 0.8700 0.4472
1.5216 7.9111 -1.2478 0.1108 0.4667 0.8774
-8.1187 -0.0068 7.8463 -0.2215 -0.9227 0.3155
-7.2735 -3.6439 6.9270 -0.2303 -0.9618 -0.1481
0.9727 -7.9937 -0.3394 0.0198 -0.2364 -0.9715
4.6332 5.2743 -7.5307 -0.0730 0.9162 0.3939
6.4989 -1.9684 -9.2853 -0.0662 0.8439 -0.5324
-6.5569 -0.3049 9.6808 0.0756 -0.9594 0.2718
5.2537 -4.6600 -7.9633 -0.1088 0.5907 -0.7995
-5.9726 0.9369 9.9827 0.1662 -0.8972 0.4091
-4.4920 -4.4645 8.6101 0.1754 -0.9424 -0.2849
1.4471 -7.8722 0.6705 0.1462 -0.2667 -0.9526
3.9205 -2.4266 -10.2101 -0.4016 0.7401 -0.5395
-0.3337 7.4239 -3.7231 -0.2704 0.4955 0.8254
-2.9235 -2.3967 10.2901 0.4769 -0.8774 -0.0520
-3.6734 0.4211 10.7453 0.4544 -0.8368 0.3054
5.9074 -5.7875 -0.0574 0.5564 0.1041 -0.8244
7.0418 0.0356 3.4285 0.9772 0.1816 -0.1100
-7.0578 0.0371 -3.3996 -0.9761 -0.1815 0.1194
-7.2501 1.8677 -2.5695 -0.9199 -0.1712 0.3529
-5.9149 5.7785 0.0492 -0.5578 -0.1043 0.8234
-7.7262 -2.6255 -0.9021 -0.8699 -0.4730 -0.1397
-8.4919 0.0533 0.0180 -0.8593 -0.4668 0.2090
6.9611 3.8907 1.3366 0.8340 0.4537 0.3140
7.9386 2.1557 0.7407 0.8760 0.4762 0.0767
8.4582 -1.6634 -0.5710 0.8028 0.4359 -0.4067
-7.1696 -1.5995 -2.8590 -0.9568 -0.2839 -0.0625
-7.7271 0.8260 -1.9562 -0.9281 -0.2751 0.2510
