#------------------------------------------------------------------------------
#$Date: 2025-04-11 11:37:00 +0300 (Fri, 11 Apr 2025) $
#$Revision: 299263 $
#$URL: file:///home/coder/svn-repositories/cod/cif/3/00/05/3000559.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_3000559
loop_
_publ_author_name
'Gogoi, Diptajyoti'
'Sasaki, Toshiyuki'
'Kalita, Nabadeep'
'Sethi, Tapaswini'
'Ichiyanagi, Kouhei'
'Nakane, Takanori'
'Kawamoto, Akihiro'
'Das, Dinabandhu'
'Kurisu, Genji'
'Thakuria, Ranjit'
_publ_section_title
;
 Tuning of a Hydrogen-Bonded Organic Framework by Liquid-Assisted
 Mechanosynthesis between Trans-Aconitic Acid and Isonicotinamide
;
_journal_name_full               'Chemistry A European Journal'
_journal_page_first              e202403427(1)
_journal_page_last               e202403427(10)
_journal_paper_doi               10.1002/chem.202403427
_journal_volume                  31
_journal_year                    2025
_chemical_formula_moiety         'C6 H6 O6, 1.5(C6 H6 N2 O), 1.168(C2 H3 N)'
_chemical_formula_sum            'C17.34 H18.5 N4.17 O7.5'
_chemical_formula_weight         405.23
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-03-27
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_cell_angle_alpha                78.119(2)
_cell_angle_beta                 84.652(2)
_cell_angle_gamma                88.580(2)
_cell_formula_units_Z            4
_cell_length_a                   6.98750(10)
_cell_length_b                   15.1552(3)
_cell_length_c                   19.5219(4)
_cell_measurement_reflns_used    14841
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.1960
_cell_measurement_theta_min      2.1620
_cell_volume                     2014.18(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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_temperature      100(2)
_diffrn_detector                 'Dectris Eiger X 1M'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'DECTRIS EIGER X 1M'
_diffrn_measurement_method       'Shutterless ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0050608000
_diffrn_orient_matrix_UB_12      0.0154623000
_diffrn_orient_matrix_UB_13      -0.0421661000
_diffrn_orient_matrix_UB_21      0.0444486000
_diffrn_orient_matrix_UB_22      0.0486932000
_diffrn_orient_matrix_UB_23      0.0009354000
_diffrn_orient_matrix_UB_31      0.1078044000
_diffrn_orient_matrix_UB_32      -0.0196911000
_diffrn_orient_matrix_UB_33      -0.0065262000
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.812
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20365
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        29.157
_diffrn_reflns_theta_max         30.497
_diffrn_reflns_theta_min         1.569
_diffrn_source                   'Synchrotron radiation SPring-8 BL40XU'
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83307
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       plate
_exptl_crystal_F_000             847
_refine_diff_density_max         0.689
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.113
_refine_ls_extinction_coef       0.158(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     676
_refine_ls_number_reflns         8226
_refine_ls_number_restraints     63
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0667
_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)+(0.1230P)²+0.9835P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1886
_refine_ls_wR_factor_ref         0.1916
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7481
_reflns_number_total             8226
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            1TACA1INA-EtACN_fill.cif
_cod_data_source_block           1taca1ina-etacn
_cod_depositor_comments
'Releasing structure 3000559 into public domain as published material.'
_cod_original_formula_sum        'C17.34 H18.50 N4.17 O7.50'
_cod_database_code               3000559
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C68) \\sim Ueq, Uanis(N70) \\sim Ueq, Uanis(C69) \\sim Ueq, Uanis(N64)
\\sim Ueq, Uanis(C63) \\sim Ueq, Uanis(C62) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
3. Rigid body (RIGU) restrains
 N70, C69, C68, N64, C63, C62, C65, N67, C66
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(O55B)=Sof(H55B)=Sof(O56B)=Sof(C28)=Sof(C29)=Sof(H29)=Sof(C33)=Sof(H33)=
 Sof(N31)=Sof(C34)=Sof(C32)=Sof(H32)=Sof(N36)=Sof(H36A)=Sof(H36B)=Sof(O37)=
 Sof(C30)=Sof(H30)=Sof(O43B)=Sof(O44B)=Sof(H44B)=1-FVAR(1)
 Sof(O44A)=Sof(H44A)=Sof(O43A)=Sof(O27)=Sof(C19)=Sof(N26)=Sof(H26A)=Sof(H26B)=
 Sof(C21)=Sof(H21)=Sof(N22)=Sof(C23)=Sof(H23)=Sof(C20)=Sof(H20)=Sof(C24)=
 Sof(H24)=Sof(C25)=Sof(O56A)=Sof(O55A)=Sof(H55A)=FVAR(1)
 Sof(N67)=Sof(C65)=Sof(H65A)=Sof(H65B)=Sof(H65C)=Sof(C66)=FVAR(2)
 Sof(C63)=Sof(N64)=Sof(C62)=Sof(H62A)=Sof(H62B)=Sof(H62C)=FVAR(3)
 Sof(C69)=Sof(N70)=Sof(C68)=Sof(H68A)=Sof(H68B)=Sof(H68C)=FVAR(4)
5.a Secondary CH2 refined with riding coordinates:
 C51(H51A,H51B), C39(H39A,H39B)
5.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C11(H11), C14(H14), C3(H3), C53(H53), C12(H12), C5(H5), C2(H2),
 C41(H41), C15(H15), C21(H21), C23(H23), C20(H20), C24(H24), C29(H29), C33(H33),
  C32(H32), C30(H30)
5.c X=CH2 refined with riding coordinates:
 N17(H17A,H17B), N8(H8A,H8B), N26(H26A,H26B), N36(H36A,H36B)
5.d Idealised Me refined as rotating group:
 C65(H65A,H65B,H65C), C68(H68A,H68B,H68C), C62(H62A,H62B,H62C)
5.e Idealised tetrahedral OH refined as rotating group:
 O60(H60), O57(H57), O48(H48), O44A(H44A), O45(H45), O55B(H55B), O44B(H44B),
 O55A(H55A)
;
_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 1.793
_oxdiff_exptl_absorpt_empirical_full_min 0.655
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
O58 O 0.41969(18) 1.27994(8) 0.05170(7) 0.0315(3) Uani 1 1 d . . . . .
O46 O 1.08762(19) 0.80468(8) 0.94942(7) 0.0328(3) Uani 1 1 d . . . . .
O60 O 0.22032(19) 0.91066(8) 0.20037(7) 0.0315(3) Uani 1 1 d . . . . .
H60 H 0.233881 0.859356 0.190481 0.047 Uiso 1 1 calc R U . . .
O18 O 0.22779(18) 0.74723(8) 0.18165(7) 0.0307(3) Uani 1 1 d . . . . .
O9 O 1.27860(18) 0.33618(8) 0.81999(7) 0.0312(3) Uani 1 1 d . . . . .
O57 O 0.24530(18) 1.26074(8) 0.15575(7) 0.0303(3) Uani 1 1 d . . . . .
H57 H 0.256460 1.317001 0.149068 0.045 Uiso 1 1 calc R U . . .
O49 O 1.16803(19) 0.49781(8) 0.91373(7) 0.0337(3) Uani 1 1 d . . . . .
O48 O 1.29158(19) 0.50813(8) 0.80251(7) 0.0325(3) Uani 1 1 d . . . . .
H48 H 1.284628 0.451637 0.813314 0.049 Uiso 1 1 calc R U . . .
O61 O 0.33234(19) 0.95661(8) 0.08773(7) 0.0328(3) Uani 1 1 d . . . . .
O44A O 1.0446(15) 0.7031(9) 0.7290(6) 0.049(3) Uani 0.502(5) 1 d . . P A 1
H44A H 0.991082 0.719113 0.691620 0.060(18) Uiso 0.502(5) 1 calc R . P A 1
O45 O 1.24231(18) 0.83579(8) 0.84151(7) 0.0318(3) Uani 1 1 d . . . . .
H45 H 1.234427 0.888825 0.848175 0.048 Uiso 1 1 calc R U . . .
O55B O 0.4703(12) 1.0669(5) 0.2737(4) 0.0300(12) Uani 0.498(5) 1 d . . P A 2
H55B H 0.526093 1.052994 0.310747 0.045 Uiso 0.498(5) 1 calc R U P A 2
N17 N 0.3805(2) 0.77077(9) 0.07212(8) 0.0265(3) Uani 1 1 d . . . . .
H17A H 0.385419 0.829394 0.069267 0.032 Uiso 1 1 calc R U . . .
H17B H 0.429284 0.747119 0.036725 0.032 Uiso 1 1 calc R U . . .
N8 N 1.1194(2) 0.30494(9) 0.92853(8) 0.0277(3) Uani 1 1 d . . . . .
H8A H 1.116400 0.362021 0.931805 0.033 Uiso 1 1 calc R U . . .
H8B H 1.067427 0.263736 0.963339 0.033 Uiso 1 1 calc R U . . .
O56B O 0.2187(8) 1.0095(6) 0.3440(5) 0.0435(14) Uani 0.498(5) 1 d . . P A 2
N13 N 0.2606(2) 0.43285(9) 0.14368(8) 0.0269(3) Uani 1 1 d . . . . .
N4 N 1.2278(2) 0.00320(9) 0.85475(8) 0.0280(3) Uani 1 1 d . . . . .
O43A O 1.308(4) 0.7613(12) 0.6583(12) 0.075(4) Uani 0.502(5) 1 d . . P A 1
C6 C 1.1696(2) 0.11329(11) 0.92632(9) 0.0286(4) Uani 1 1 d . . . . .
H6 H 1.135466 0.126373 0.971438 0.034 Uiso 1 1 calc R U . . .
C11 C 0.3372(2) 0.57900(11) 0.07434(9) 0.0270(4) Uani 1 1 d . . . . .
H11 H 0.380787 0.615197 0.030139 0.032 Uiso 1 1 calc R U . . .
C14 C 0.2145(2) 0.47032(11) 0.19957(9) 0.0283(4) Uani 1 1 d . . . . .
H14 H 0.172355 0.432422 0.243205 0.034 Uiso 1 1 calc R U . . .
C51 C 0.1537(2) 1.07728(11) 0.22773(9) 0.0265(4) Uani 1 1 d . . . . .
H51A H 0.031703 1.043273 0.235619 0.032 Uiso 1 1 calc R U . . .
H51B H 0.121303 1.141672 0.225761 0.032 Uiso 1 1 calc R U . . .
C3 C 1.2630(3) 0.07007(12) 0.79849(10) 0.0316(4) Uani 1 1 d . . . . .
H3 H 1.294570 0.054982 0.753895 0.038 Uiso 1 1 calc R U . . .
C53 C 0.3325(2) 1.13213(11) 0.10701(9) 0.0256(4) Uani 1 1 d . . . . .
H53 H 0.393931 1.112294 0.067326 0.031 Uiso 1 1 calc R U . . .
C12 C 0.3191(2) 0.48632(11) 0.08214(9) 0.0282(4) Uani 1 1 d . . . . .
H12 H 0.349449 0.459914 0.042320 0.034 Uiso 1 1 calc R U . . .
C39 C 1.3528(3) 0.69072(11) 0.77549(9) 0.0285(4) Uani 1 1 d . . . . .
H39A H 1.449147 0.648633 0.759430 0.034 Uiso 1 1 calc R U . . .
H39B H 1.423077 0.742777 0.784040 0.034 Uiso 1 1 calc R U . . .
C1 C 1.2068(2) 0.18270(11) 0.86770(9) 0.0247(3) Uani 1 1 d . . . . .
C54 C 0.3357(2) 1.23153(11) 0.10319(9) 0.0254(4) Uani 1 1 d . . . . .
C10 C 0.2904(2) 0.61791(10) 0.13240(9) 0.0237(3) Uani 1 1 d . . . . .
C5 C 1.1835(2) 0.02444(11) 0.91742(10) 0.0290(4) Uani 1 1 d . . . . .
H5 H 1.160507 -0.022863 0.957466 0.035 Uiso 1 1 calc R U . . .
C2 C 1.2551(3) 0.16038(12) 0.80269(10) 0.0303(4) Uani 1 1 d . . . . .
H2 H 1.282225 0.206115 0.761863 0.036 Uiso 1 1 calc R U . . .
C7 C 1.2021(2) 0.28112(11) 0.87134(9) 0.0257(3) Uani 1 1 d . . . . .
C16 C 0.2995(2) 0.71810(11) 0.12975(9) 0.0245(3) Uani 1 1 d . . . . .
C42 C 1.1630(2) 0.78069(11) 0.89681(10) 0.0278(4) Uani 1 1 d . . . . .
C41 C 1.1683(2) 0.68283(11) 0.89463(10) 0.0283(4) Uani 1 1 d . . . . .
H41 H 1.106642 0.643491 0.934348 0.034 Uiso 1 1 calc R U . . .
C15 C 0.2263(2) 0.56238(11) 0.19600(9) 0.0275(4) Uani 1 1 d . . . . .
H15 H 0.191071 0.587140 0.236345 0.033 Uiso 1 1 calc R U . . .
C52 C 0.2553(2) 1.06721(11) 0.15837(9) 0.0248(3) Uani 1 1 d . . . . .
C59 C 0.2746(2) 0.97249(11) 0.14471(9) 0.0255(4) Uani 1 1 d . . . . .
C47 C 1.2313(2) 0.54225(11) 0.85731(9) 0.0279(4) Uani 1 1 d . . . . .
O27 O 0.4468(9) 0.9415(4) 0.4409(4) 0.0462(14) Uani 0.502(5) 1 d . . P A 1
C40 C 1.2494(2) 0.64390(11) 0.84353(9) 0.0272(4) Uani 1 1 d . . . . .
C38 C 1.2242(5) 0.72386(15) 0.71761(13) 0.0543(7) Uani 1 1 d . . . . .
C50 C 0.2714(5) 1.04415(15) 0.28870(11) 0.0502(6) Uani 1 1 d . . . . .
C19 C 0.7301(16) 0.8876(7) 0.4938(4) 0.0356(17) Uani 0.502(5) 1 d . . P A 1
N26 N 0.7241(8) 0.9961(4) 0.3836(3) 0.0367(11) Uani 0.502(5) 1 d . . P A 1
H26A H 0.665703 1.031056 0.349910 0.044 Uiso 0.502(5) 1 calc R U P A 1
H26B H 0.850330 0.995926 0.382148 0.044 Uiso 0.502(5) 1 calc R U P A 1
C21 C 0.7097(9) 0.7911(4) 0.6073(3) 0.0417(13) Uani 0.502(5) 1 d . . P A 1
H21 H 0.633285 0.758762 0.646845 0.050 Uiso 0.502(5) 1 calc R U P A 1
N22 N 0.8998(5) 0.7858(3) 0.6075(2) 0.0361(9) Uani 0.502(5) 1 d . . P A 1
C23 C 1.0056(19) 0.8279(11) 0.5508(7) 0.049(2) Uani 0.502(5) 1 d . . P A 1
H23 H 1.141438 0.821777 0.549374 0.059 Uiso 0.502(5) 1 calc R U P A 1
C20 C 0.6182(6) 0.8410(3) 0.5527(2) 0.0420(12) Uani 0.502(5) 1 d . . P A 1
H20 H 0.481836 0.843847 0.554968 0.050 Uiso 0.502(5) 1 calc R U P A 1
C24 C 0.9254(6) 0.8806(3) 0.4934(2) 0.0446(12) Uani 0.502(5) 1 d . . P A 1
H24 H 1.005756 0.911408 0.454241 0.054 Uiso 0.502(5) 1 calc R U P A 1
C25 C 0.6236(6) 0.9447(3) 0.4355(3) 0.0354(10) Uani 0.502(5) 1 d . . P A 1
C28 C 0.7562(16) 0.8749(8) 0.5149(4) 0.0375(18) Uani 0.498(5) 1 d . . P A 2
C29 C 0.8659(6) 0.9345(3) 0.4620(2) 0.0422(12) Uani 0.498(5) 1 d . . P A 2
H29 H 0.998833 0.942800 0.465184 0.051 Uiso 0.498(5) 1 calc R U P A 2
C33 C 0.5673(6) 0.8632(4) 0.5068(2) 0.0493(13) Uani 0.498(5) 1 d . . P A 2
H33 H 0.490233 0.823271 0.541865 0.059 Uiso 0.498(5) 1 calc R U P A 2
N31 N 0.5890(5) 0.9699(3) 0.3983(2) 0.0380(10) Uani 0.498(5) 1 d . . P A 2
C34 C 0.8617(6) 0.8236(4) 0.5758(3) 0.0346(10) Uani 0.498(5) 1 d . . P A 2
C32 C 0.4885(13) 0.9097(7) 0.4474(6) 0.051(2) Uani 0.498(5) 1 d . . P A 2
H32 H 0.358739 0.898519 0.441158 0.061 Uiso 0.498(5) 1 calc R U P A 2
N36 N 0.7578(7) 0.7819(3) 0.6317(3) 0.0343(11) Uani 0.498(5) 1 d . . P A 2
H36A H 0.814057 0.752530 0.668280 0.041 Uiso 0.498(5) 1 calc R U P A 2
H36B H 0.631553 0.783168 0.632846 0.041 Uiso 0.498(5) 1 calc R U P A 2
O37 O 1.0399(12) 0.8258(8) 0.5691(4) 0.0480(16) Uani 0.498(5) 1 d . . P A 2
C30 C 0.7748(9) 0.9813(5) 0.4047(3) 0.0425(14) Uani 0.498(5) 1 d . . P A 2
H30 H 0.847220 1.022612 0.369117 0.051 Uiso 0.498(5) 1 calc R U P A 2
N67 N 0.1324(11) 0.4956(4) 0.3694(2) 0.136(3) Uani 0.736(6) 1 d . . P . .
C65 C 0.1402(11) 0.3812(4) 0.4909(3) 0.106(2) Uani 0.736(6) 1 d . . P . .
H65A H 0.092652 0.411402 0.529012 0.159 Uiso 0.736(6) 1 calc R U P . .
H65B H 0.271465 0.359273 0.497912 0.159 Uiso 0.736(6) 1 calc R U P . .
H65C H 0.056736 0.330232 0.490792 0.159 Uiso 0.736(6) 1 calc R U P . .
C66 C 0.1398(9) 0.4472(4) 0.4214(3) 0.0937(17) Uani 0.736(6) 1 d . . P . .
C69 C 0.9478(16) 0.2411(4) 0.6449(3) 0.124(2) Uani 0.751(7) 1 d . U P . .
N70 N 1.1469(15) 0.2411(5) 0.6378(3) 0.160(3) Uani 0.751(7) 1 d . U P . .
C68 C 0.7362(13) 0.2459(5) 0.6457(3) 0.126(2) Uani 0.751(7) 1 d . U P . .
H68A H 0.683002 0.272441 0.685181 0.189 Uiso 0.751(7) 1 calc R U P . .
H68B H 0.684818 0.185013 0.651044 0.189 Uiso 0.751(7) 1 calc R U P . .
H68C H 0.700481 0.283320 0.601542 0.189 Uiso 0.751(7) 1 calc R U P . .
C63 C 0.6406(15) 0.4535(9) 0.4187(7) 0.195(4) Uani 0.850(8) 1 d . U P . .
N64 N 0.6509(14) 0.3879(8) 0.4769(6) 0.236(5) Uani 0.850(8) 1 d . U P . .
C62 C 0.6384(14) 0.5266(8) 0.3568(3) 0.194(4) Uani 0.850(8) 1 d . U P . .
H62A H 0.759185 0.525958 0.326970 0.291 Uiso 0.850(8) 1 calc R U P . .
H62B H 0.624313 0.584496 0.371681 0.291 Uiso 0.850(8) 1 calc R U P . .
H62C H 0.530382 0.518312 0.330145 0.291 Uiso 0.850(8) 1 calc R U P . .
O43B O 1.055(2) 0.7045(9) 0.7237(5) 0.052(4) Uani 0.498(5) 1 d . . P A 2
O44B O 1.298(4) 0.7806(11) 0.6653(12) 0.063(4) Uani 0.498(5) 1 d . . P A 2
H44B H 1.226798 0.786228 0.632179 0.070(19) Uiso 0.498(5) 1 calc R . P A 2
O56A O 0.4286(12) 1.0461(6) 0.2849(4) 0.0343(13) Uani 0.502(5) 1 d . . P A 1
O55A O 0.1535(7) 1.0044(5) 0.3489(4) 0.0321(11) Uani 0.502(5) 1 d . . P A 1
H55A H 0.221840 0.985733 0.382227 0.048 Uiso 0.502(5) 1 calc R U P A 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0045 0.0022 '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 0.0085 0.0045 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0147 0.0082 '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
C59 O60 H60 109.5 . .
C54 O57 H57 109.5 . .
C47 O48 H48 109.5 . .
C38 O44A H44A 109.5 . .
C42 O45 H45 109.5 . .
C50 O55B H55B 109.5 . .
H17A N17 H17B 120.0 . .
C16 N17 H17A 120.0 . .
C16 N17 H17B 120.0 . .
H8A N8 H8B 120.0 . .
C7 N8 H8A 120.0 . .
C7 N8 H8B 120.0 . .
C12 N13 C14 118.77(14) . .
C5 N4 C3 118.60(14) . .
C1 C6 H6 120.6 . .
C5 C6 H6 120.6 . .
C5 C6 C1 118.72(16) . .
C12 C11 H11 120.6 . .
C12 C11 C10 118.84(15) . .
C10 C11 H11 120.6 . .
N13 C14 H14 118.8 . .
N13 C14 C15 122.39(16) . .
C15 C14 H14 118.8 . .
H51A C51 H51B 107.8 . .
C52 C51 H51A 109.0 . .
C52 C51 H51B 109.0 . .
C52 C51 C50 113.04(16) . .
C50 C51 H51A 109.0 . .
C50 C51 H51B 109.0 . .
N4 C3 H3 118.6 . .
N4 C3 C2 122.73(17) . .
C2 C3 H3 118.6 . .
C54 C53 H53 115.5 . .
C52 C53 H53 115.5 . .
C52 C53 C54 129.10(16) . .
N13 C12 C11 122.43(16) . .
N13 C12 H12 118.8 . .
C11 C12 H12 118.8 . .
H39A C39 H39B 107.6 . .
C40 C39 H39A 108.7 . .
C40 C39 H39B 108.7 . .
C40 C39 C38 114.42(19) . .
C38 C39 H39A 108.7 . .
C38 C39 H39B 108.7 . .
C6 C1 C7 123.39(16) . .
C2 C1 C6 118.64(15) . .
C2 C1 C7 117.95(15) . .
O58 C54 O57 124.46(15) . .
O58 C54 C53 118.99(15) . .
O57 C54 C53 116.55(15) . .
C11 C10 C16 123.51(15) . .
C15 C10 C11 118.62(14) . .
C15 C10 C16 117.84(15) . .
N4 C5 C6 122.52(16) . .
N4 C5 H5 118.7 . .
C6 C5 H5 118.7 . .
C3 C2 C1 118.78(16) . .
C3 C2 H2 120.6 . .
C1 C2 H2 120.6 . .
O9 C7 N8 123.28(15) . .
O9 C7 C1 118.03(15) . .
N8 C7 C1 118.69(15) . .
O18 C16 N17 123.22(14) . .
O18 C16 C10 118.17(15) . .
N17 C16 C10 118.61(15) . .
O46 C42 O45 124.14(15) . .
O46 C42 C41 119.20(16) . .
O45 C42 C41 116.66(16) . .
C42 C41 H41 116.1 . .
C40 C41 C42 127.79(16) . .
C40 C41 H41 116.1 . .
C14 C15 C10 118.93(16) . .
C14 C15 H15 120.5 . .
C10 C15 H15 120.5 . .
C51 C52 C59 116.74(14) . .
C53 C52 C51 127.72(15) . .
C53 C52 C59 115.54(15) . .
O60 C59 C52 112.72(14) . .
O61 C59 O60 124.40(15) . .
O61 C59 C52 122.87(15) . .
O49 C47 O48 124.27(15) . .
O49 C47 C40 122.78(16) . .
O48 C47 C40 112.95(15) . .
C39 C40 C47 118.31(15) . .
C41 C40 C39 126.56(15) . .
C41 C40 C47 115.13(15) . .
O44A C38 C39 118.2(5) . .
O43A C38 O44A 125.1(13) . .
O43A C38 C39 116.2(12) . .
O43B C38 C39 121.9(5) . .
O43B C38 O44B 121.6(13) . .
O44B C38 C39 116.0(12) . .
O55B C50 C51 113.5(4) . .
O56B C50 O55B 118.6(5) . .
O56B C50 C51 127.7(4) . .
O56A C50 C51 123.9(4) . .
O56A C50 O55A 125.1(5) . .
O55A C50 C51 110.8(3) . .
C20 C19 C25 117.0(8) . .
C24 C19 C20 118.1(6) . .
C24 C19 C25 124.9(7) . .
H26A N26 H26B 120.0 . .
C25 N26 H26A 120.0 . .
C25 N26 H26B 120.0 . .
N22 C21 H21 118.3 . .
N22 C21 C20 123.3(5) . .
C20 C21 H21 118.3 . .
C23 N22 C21 118.0(7) . .
N22 C23 H23 118.7 . .
N22 C23 C24 122.6(10) . .
C24 C23 H23 118.7 . .
C19 C20 H20 120.7 . .
C21 C20 C19 118.6(5) . .
C21 C20 H20 120.7 . .
C19 C24 C23 119.3(8) . .
C19 C24 H24 120.3 . .
C23 C24 H24 120.3 . .
O27 C25 C19 118.2(7) . .
O27 C25 N26 123.6(7) . .
N26 C25 C19 118.2(6) . .
C29 C28 C34 116.8(8) . .
C33 C28 C29 118.6(6) . .
C33 C28 C34 124.6(8) . .
C28 C29 H29 120.8 . .
C30 C29 C28 118.3(6) . .
C30 C29 H29 120.8 . .
C28 C33 H33 120.1 . .
C28 C33 C32 119.8(6) . .
C32 C33 H33 120.1 . .
C30 N31 C32 118.9(7) . .
N36 C34 C28 117.6(6) . .
O37 C34 C28 117.5(7) . .
O37 C34 N36 124.9(7) . .
C33 C32 H32 118.9 . .
N31 C32 C33 122.2(8) . .
N31 C32 H32 118.9 . .
C34 N36 H36A 120.0 . .
C34 N36 H36B 120.0 . .
H36A N36 H36B 120.0 . .
C29 C30 H30 118.9 . .
N31 C30 C29 122.1(5) . .
N31 C30 H30 118.9 . .
H65A C65 H65B 109.5 . .
H65A C65 H65C 109.5 . .
H65B C65 H65C 109.5 . .
C66 C65 H65A 109.5 . .
C66 C65 H65B 109.5 . .
C66 C65 H65C 109.5 . .
N67 C66 C65 177.4(8) . .
N70 C69 C68 174.7(6) . .
C69 C68 H68A 109.5 . .
C69 C68 H68B 109.5 . .
C69 C68 H68C 109.5 . .
H68A C68 H68B 109.5 . .
H68A C68 H68C 109.5 . .
H68B C68 H68C 109.5 . .
N64 C63 C62 176.9(13) . .
C63 C62 H62A 109.5 . .
C63 C62 H62B 109.5 . .
C63 C62 H62C 109.5 . .
H62A C62 H62B 109.5 . .
H62A C62 H62C 109.5 . .
H62B C62 H62C 109.5 . .
C38 O44B H44B 109.5 . .
C50 O55A H55A 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O58 C54 1.225(2) .
O46 C42 1.228(2) .
O60 H60 0.8400 .
O60 C59 1.313(2) .
O18 C16 1.245(2) .
O9 C7 1.251(2) .
O57 H57 0.8400 .
O57 C54 1.304(2) .
O49 C47 1.217(2) .
O48 H48 0.8400 .
O48 C47 1.312(2) .
O61 C59 1.216(2) .
O44A H44A 0.8400 .
O44A C38 1.290(11) .
O45 H45 0.8400 .
O45 C42 1.308(2) .
O55B H55B 0.8400 .
O55B C50 1.429(7) .
N17 H17A 0.8800 .
N17 H17B 0.8800 .
N17 C16 1.326(2) .
N8 H8A 0.8800 .
N8 H8B 0.8800 .
N8 C7 1.321(2) .
O56B C50 1.131(8) .
N13 C14 1.341(2) .
N13 C12 1.339(2) .
N4 C3 1.341(2) .
N4 C5 1.335(2) .
O43A C38 1.27(2) .
C6 H6 0.9500 .
C6 C1 1.395(2) .
C6 C5 1.393(2) .
C11 H11 0.9500 .
C11 C12 1.389(2) .
C11 C10 1.391(2) .
C14 H14 0.9500 .
C14 C15 1.387(2) .
C51 H51A 0.9900 .
C51 H51B 0.9900 .
C51 C52 1.504(2) .
C51 C50 1.504(3) .
C3 H3 0.9500 .
C3 C2 1.387(2) .
C53 H53 0.9500 .
C53 C54 1.494(2) .
C53 C52 1.335(2) .
C12 H12 0.9500 .
C39 H39A 0.9900 .
C39 H39B 0.9900 .
C39 C40 1.500(2) .
C39 C38 1.506(3) .
C1 C2 1.389(3) .
C1 C7 1.507(2) .
C10 C16 1.511(2) .
C10 C15 1.391(2) .
C5 H5 0.9500 .
C2 H2 0.9500 .
C42 C41 1.492(2) .
C41 H41 0.9500 .
C41 C40 1.336(3) .
C15 H15 0.9500 .
C52 C59 1.514(2) .
C47 C40 1.515(2) .
O27 C25 1.231(7) .
C38 O43B 1.216(13) .
C38 O44B 1.27(2) .
C50 O56A 1.094(9) .
C50 O55A 1.406(7) .
C19 C20 1.400(10) .
C19 C24 1.366(12) .
C19 C25 1.522(9) .
N26 H26A 0.8800 .
N26 H26B 0.8800 .
N26 C25 1.303(8) .
C21 H21 0.9500 .
C21 N22 1.329(7) .
C21 C20 1.373(8) .
N22 C23 1.326(16) .
C23 H23 0.9500 .
C23 C24 1.392(12) .
C20 H20 0.9500 .
C24 H24 0.9500 .
C28 C29 1.405(11) .
C28 C33 1.364(12) .
C28 C34 1.522(9) .
C29 H29 0.9500 .
C29 C30 1.393(8) .
C33 H33 0.9500 .
C33 C32 1.381(11) .
N31 C32 1.338(11) .
N31 C30 1.334(7) .
C34 N36 1.308(7) .
C34 O37 1.240(10) .
C32 H32 0.9500 .
N36 H36A 0.8800 .
N36 H36B 0.8800 .
C30 H30 0.9500 .
N67 C66 1.128(7) .
C65 H65A 0.9800 .
C65 H65B 0.9800 .
C65 H65C 0.9800 .
C65 C66 1.511(7) .
C69 N70 1.385(12) .
C69 C68 1.477(12) .
C68 H68A 0.9800 .
C68 H68B 0.9800 .
C68 H68C 0.9800 .
C63 N64 1.354(14) .
C63 C62 1.463(14) .
C62 H62A 0.9800 .
C62 H62B 0.9800 .
C62 H62C 0.9800 .
O44B H44B 0.8400 .
O55A H55A 0.8400 .
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
O46 C42 C41 C40 -177.40(17) . . . .
O49 C47 C40 C39 172.08(15) . . . .
O49 C47 C40 C41 -8.2(2) . . . .
O48 C47 C40 C39 -7.6(2) . . . .
O48 C47 C40 C41 172.09(15) . . . .
O45 C42 C41 C40 2.0(3) . . . .
N13 C14 C15 C10 -0.8(3) . . . .
N4 C3 C2 C1 -0.7(3) . . . .
C6 C1 C2 C3 0.5(2) . . . .
C6 C1 C7 O9 164.09(16) . . . .
C6 C1 C7 N8 -15.3(2) . . . .
C11 C10 C16 O18 169.48(15) . . . .
C11 C10 C16 N17 -9.6(2) . . . .
C11 C10 C15 C14 1.1(2) . . . .
C14 N13 C12 C11 1.2(2) . . . .
C51 C52 C59 O60 -8.4(2) . . . .
C51 C52 C59 O61 170.77(15) . . . .
C3 N4 C5 C6 1.0(3) . . . .
C53 C52 C59 O60 171.17(14) . . . .
C53 C52 C59 O61 -9.7(2) . . . .
C12 N13 C14 C15 -0.3(2) . . . .
C12 C11 C10 C16 -178.33(15) . . . .
C12 C11 C10 C15 -0.3(2) . . . .
C1 C6 C5 N4 -1.2(3) . . . .
C54 C53 C52 C51 -1.6(3) . . . .
C54 C53 C52 C59 178.92(15) . . . .
C10 C11 C12 N13 -0.8(3) . . . .
C5 N4 C3 C2 0.0(3) . . . .
C5 C6 C1 C2 0.4(2) . . . .
C5 C6 C1 C7 -178.09(15) . . . .
C2 C1 C7 O9 -14.4(2) . . . .
C2 C1 C7 N8 166.25(15) . . . .
C7 C1 C2 C3 179.06(15) . . . .
C16 C10 C15 C14 179.24(14) . . . .
C42 C41 C40 C39 -0.8(3) . . . .
C42 C41 C40 C47 179.56(15) . . . .
C15 C10 C16 O18 -8.5(2) . . . .
C15 C10 C16 N17 172.44(14) . . . .
C52 C51 C50 O55B 40.2(5) . . . .
C52 C51 C50 O56B -145.0(6) . . . .
C52 C51 C50 O56A 30.6(6) . . . .
C52 C51 C50 O55A -144.8(3) . . . .
C52 C53 C54 O58 177.94(16) . . . .
C52 C53 C54 O57 -2.8(2) . . . .
C40 C39 C38 O44A -5.8(7) . . . .
C40 C39 C38 O43A -177.7(9) . . . .
C40 C39 C38 O43B -8.2(8) . . . .
C40 C39 C38 O44B 164.6(11) . . . .
C38 C39 C40 C41 -86.3(2) . . . .
C38 C39 C40 C47 93.35(19) . . . .
C50 C51 C52 C53 -106.8(2) . . . .
C50 C51 C52 C59 72.7(2) . . . .
C21 N22 C23 C24 3.4(17) . . . .
N22 C21 C20 C19 1.1(10) . . . .
N22 C23 C24 C19 -2.1(18) . . . .
C20 C19 C24 C23 0.1(14) . . . .
C20 C19 C25 O27 -5.3(11) . . . .
C20 C19 C25 N26 172.9(6) . . . .
C20 C21 N22 C23 -2.9(12) . . . .
C24 C19 C20 C21 0.4(12) . . . .
C24 C19 C25 O27 176.5(8) . . . .
C24 C19 C25 N26 -5.3(12) . . . .
C25 C19 C20 C21 -178.0(6) . . . .
C25 C19 C24 C23 178.3(10) . . . .
C28 C29 C30 N31 -1.1(10) . . . .
C28 C33 C32 N31 -3.4(14) . . . .
C29 C28 C33 C32 0.1(14) . . . .
C29 C28 C34 N36 166.8(7) . . . .
C29 C28 C34 O37 -12.0(12) . . . .
C33 C28 C29 C30 2.1(12) . . . .
C33 C28 C34 N36 -16.8(12) . . . .
C33 C28 C34 O37 164.4(10) . . . .
C34 C28 C29 C30 178.7(6) . . . .
C34 C28 C33 C32 -176.3(9) . . . .
C32 N31 C30 C29 -2.0(10) . . . .
C30 N31 C32 C33 4.3(13) . . . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
_cod_related_entry_description
1 XRDa 00269 10.51093/xrd-00269
