# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p
_database_code_depnum_ccdc_archive 'CCDC 2235394'
loop_
_audit_author_name
_audit_author_address
'Bao Li'
;Huazhong university of science and technology
China
;
_audit_update_record             
;
2023-01-10 deposited with the CCDC.	2023-07-25 downloaded from the CCDC.
;
_audit_creation_date             2022-12-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C48 H24 N4 O16 Zr3'
_chemical_formula_sum            'C48 H24 N4 O16 Zr3'
_chemical_formula_weight         1186.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zr Zr -2.9673 0.5597 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           65
_space_group_name_H-M_alt        'C m m m'
_space_group_name_Hall           '-C 2 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x, y, -z'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z'
'x, -y, z'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'

_cell_length_a                   15.655(3)
_cell_length_b                   25.772(4)
_cell_length_c                   24.876(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     10037(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    611
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      15.36
_cell_measurement_theta_min      2.81
_shelx_estimated_absorpt_T_max   0.745
_shelx_estimated_absorpt_T_min   0.509
_exptl_absorpt_coefficient_mu    0.342
_exptl_absorpt_correction_T_max  0.7440
_exptl_absorpt_correction_T_min  0.3440
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1333 before and 0.1028 after correction.
The Ratio of minimum to maximum transmission is 0.4624.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    0.785
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2352
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1496
_diffrn_reflns_av_unetI/netI     0.0960
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            27787
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        24.708
_diffrn_reflns_theta_max         24.708
_diffrn_reflns_theta_min         1.522
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3166
_reflns_number_total             4606
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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)'
_refine_diff_density_max         2.633
_refine_diff_density_min         -1.836
_refine_diff_density_rms         0.143
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         4606
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.1143
_refine_ls_R_factor_gt           0.0879
_refine_ls_restrained_S_all      1.474
_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)+(0.1303P)²+85.0822P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2368
_refine_ls_wR_factor_ref         0.2608
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C12-C10
 2.45 with sigma of 0.02
 C13-C11
 2.45 with sigma of 0.02
2. Restrained planarity
 C4, C5, C3, C2, C7, C6
 with sigma of 0.1
 C11, C11_$1, C12, C13, C13_$1, C12_$1, C10, C10_$1, C11_$2
 with sigma of 0.1
3. Rigid bond restraints
 Zr1, Zr2, O3, O4
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 Zr1, O1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Zr1 \\sim Zr2 \\sim O3 \\sim O4: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
Zr1 \\sim O1: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
within 2A
Uanis(C8) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(O2) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.002
Uanis(Zr1) \\sim Ueq: with sigma of 0.0005 and sigma for terminal atoms of 0.002
5.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C3(H3), C4(H4), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Zr1 Zr 0.500000 0.500000 0.59826(4) 0.0224(3) Uani 1 4 d S TU P . .
Zr2 Zr 0.61311(7) 0.43117(3) 0.500000 0.0330(3) Uani 1 2 d S TU P . .
O1 O 0.5835(3) 0.55114(17) 0.64360(17) 0.0375(12) Uani 1 1 d . U . . .
O2 O 0.6581(4) 0.5967(2) 0.58255(19) 0.0577(16) Uani 1 1 d . U . . .
O5 O 0.7522(6) 0.4335(3) 0.500000 0.060(2) Uani 1 2 d S T P . .
O6 O 0.6059(7) 0.3475(3) 0.500000 0.074(3) Uani 1 2 d S T P . .
O3 O 0.6172(7) 0.500000 0.5486(3) 0.076(3) Uani 1 2 d S TU P . .
N1 N 0.7218(6) 0.7101(3) 0.8543(2) 0.069(3) Uani 1 1 d . . . . .
C2 C 0.6633(6) 0.6232(3) 0.6733(3) 0.048(2) Uani 1 1 d . . . . .
C6 C 0.6448(6) 0.6549(3) 0.7637(3) 0.057(3) Uani 1 1 d . . . . .
H6 H 0.614096 0.655367 0.795734 0.068 Uiso 1 1 calc R . . . .
C10 C 0.750000 0.750000 0.9447(4) 0.065(4) Uani 1 2 d DS T P . .
C1 C 0.6342(5) 0.5873(3) 0.6296(3) 0.043(2) Uani 1 1 d . . . . .
O4 O 0.500000 0.4309(4) 0.5482(4) 0.090(4) Uani 1 2 d S TU P . .
C7 C 0.6216(6) 0.6206(3) 0.7230(3) 0.056(2) Uani 1 1 d . . . . .
H7 H 0.578809 0.596265 0.728758 0.067 Uiso 1 1 calc R . . . .
C5 C 0.7130(6) 0.6881(3) 0.7570(3) 0.058(2) Uani 1 1 d . . . . .
C8 C 0.7323(6) 0.7267(3) 0.8003(3) 0.055(2) Uani 1 1 d . U . . .
C9 C 0.750000 0.750000 0.8840(4) 0.049(3) Uani 1 2 d S TU P . .
C3 C 0.7300(7) 0.6560(3) 0.6672(3) 0.065(3) Uani 1 1 d . . . . .
H3 H 0.758396 0.656889 0.634367 0.078 Uiso 1 1 calc R . . . .
C4 C 0.7572(6) 0.6881(3) 0.7080(3) 0.063(3) Uani 1 1 d . . . . .
H4 H 0.804325 0.709559 0.703106 0.075 Uiso 1 1 calc R . . . .
C11 C 0.7034(7) 0.7879(4) 0.9720(4) 0.096(4) Uani 1 1 d D . . . .
C12 C 0.6563(8) 0.8270(4) 0.9438(4) 0.120(6) Uani 1 1 d D . . . .
H12 H 0.655180 0.826465 0.906443 0.144 Uiso 1 1 calc R . . . .
C13 C 0.6131(11) 0.8649(5) 0.9705(5) 0.152(8) Uani 1 1 d D . . . .
H13 H 0.583958 0.890493 0.951617 0.182 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
Zr1 Zr2 3.5010(10) . ?
Zr1 Zr2 3.5010(10) 3_656 ?
Zr1 Zr2 3.5010(10) 9_666 ?
Zr1 Zr2 3.5010(10) 11_565 ?
Zr1 O1 2.172(5) . ?
Zr1 O1 2.172(5) 11_565 ?
Zr1 O1 2.172(5) 2_665 ?
Zr1 O1 2.172(5) 12_655 ?
Zr1 O3 2.211(9) . ?
Zr1 O3 2.211(9) 2_665 ?
Zr1 O4 2.173(9) 2_665 ?
Zr1 O4 2.173(9) . ?
Zr2 Zr2 3.541(2) 3_656 ?
Zr2 Zr2 3.5481(18) 11_565 ?
Zr2 O2 2.287(5) 11_565 ?
Zr2 O2 2.287(5) 4_566 ?
Zr2 O5 2.178(10) . ?
Zr2 O6 2.160(9) . ?
Zr2 O3 2.148(5) 10_556 ?
Zr2 O3 2.148(5) . ?
Zr2 O4 2.138(6) 10_556 ?
Zr2 O4 2.138(6) . ?
O1 C1 1.271(8) . ?
O2 C1 1.254(8) . ?
N1 C8 1.418(9) . ?
N1 C9 1.341(8) . ?
C2 C1 1.500(9) . ?
C2 C7 1.399(11) . ?
C2 C3 1.351(11) . ?
C6 H6 0.9300 . ?
C6 C7 1.392(10) . ?
C6 C5 1.378(11) . ?
C10 C9 1.511(14) . ?
C10 C11 1.396(12) . ?
C10 C11 1.396(12) 6_665 ?
C7 H7 0.9300 . ?
C5 C8 1.496(10) . ?
C5 C4 1.402(11) . ?
C8 C8 1.324(15) 6_665 ?
C3 H3 0.9300 . ?
C3 C4 1.378(10) . ?
C4 H4 0.9300 . ?
C11 C11 1.392(18) 10_557 ?
C11 C12 1.432(15) . ?
C12 H12 0.9300 . ?
C12 C13 1.361(17) . ?
C13 C13 1.47(3) 10_557 ?
C13 H13 0.9300 . ?

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
Zr2 Zr1 Zr2 60.76(4) 9_666 11_565 ?
Zr2 Zr1 Zr2 60.76(4) . 3_656 ?
Zr2 Zr1 Zr2 91.44(3) 3_656 11_565 ?
Zr2 Zr1 Zr2 91.44(3) . 9_666 ?
Zr2 Zr1 Zr2 60.89(3) 3_656 9_666 ?
Zr2 Zr1 Zr2 60.89(3) . 11_565 ?
O1 Zr1 Zr2 111.06(12) 12_655 11_565 ?
O1 Zr1 Zr2 111.45(14) 12_655 3_656 ?
O1 Zr1 Zr2 167.01(12) 12_655 . ?
O1 Zr1 Zr2 75.57(12) 11_565 . ?
O1 Zr1 Zr2 75.57(12) 2_665 3_656 ?
O1 Zr1 Zr2 111.06(12) . 9_666 ?
O1 Zr1 Zr2 167.01(12) 11_565 9_666 ?
O1 Zr1 Zr2 75.57(12) . 11_565 ?
O1 Zr1 Zr2 111.45(14) 2_665 9_666 ?
O1 Zr1 Zr2 111.45(14) 11_565 11_565 ?
O1 Zr1 Zr2 167.01(12) 2_665 11_565 ?
O1 Zr1 Zr2 111.06(12) 11_565 3_656 ?
O1 Zr1 Zr2 111.06(12) 2_665 . ?
O1 Zr1 Zr2 167.01(12) . 3_656 ?
O1 Zr1 Zr2 75.57(12) 12_655 9_666 ?
O1 Zr1 Zr2 111.45(14) . . ?
O1 Zr1 O1 117.4(2) . 2_665 ?
O1 Zr1 O1 74.0(3) 2_665 11_565 ?
O1 Zr1 O1 74.7(2) 2_665 12_655 ?
O1 Zr1 O1 74.0(3) . 12_655 ?
O1 Zr1 O1 74.7(2) . 11_565 ?
O1 Zr1 O1 117.4(2) 12_655 11_565 ?
O1 Zr1 O3 77.9(3) 2_665 2_665 ?
O1 Zr1 O3 142.11(14) 12_655 . ?
O1 Zr1 O3 77.9(3) 11_565 . ?
O1 Zr1 O3 142.11(13) 2_665 . ?
O1 Zr1 O3 77.9(3) 12_655 2_665 ?
O1 Zr1 O3 77.9(3) . . ?
O1 Zr1 O3 142.11(13) . 2_665 ?
O1 Zr1 O3 142.11(14) 11_565 2_665 ?
O1 Zr1 O4 142.65(15) 2_665 2_665 ?
O1 Zr1 O4 142.65(15) . . ?
O1 Zr1 O4 78.5(3) 2_665 . ?
O1 Zr1 O4 78.5(3) 11_565 . ?
O1 Zr1 O4 78.5(3) . 2_665 ?
O1 Zr1 O4 78.5(3) 12_655 2_665 ?
O1 Zr1 O4 142.65(15) 12_655 . ?
O1 Zr1 O4 142.65(15) 11_565 2_665 ?
O3 Zr1 Zr2 91.7(2) 2_665 . ?
O3 Zr1 Zr2 35.95(14) . . ?
O3 Zr1 Zr2 91.7(2) . 3_656 ?
O3 Zr1 Zr2 91.7(2) . 9_666 ?
O3 Zr1 Zr2 91.7(2) 2_665 11_565 ?
O3 Zr1 Zr2 35.95(14) 2_665 9_666 ?
O3 Zr1 Zr2 35.95(14) 2_665 3_656 ?
O3 Zr1 Zr2 35.95(14) . 11_565 ?
O3 Zr1 O3 112.1(5) . 2_665 ?
O4 Zr1 Zr2 90.9(3) . 11_565 ?
O4 Zr1 Zr2 35.37(17) . 3_656 ?
O4 Zr1 Zr2 90.9(3) 2_665 . ?
O4 Zr1 Zr2 35.37(17) 2_665 9_666 ?
O4 Zr1 Zr2 35.37(17) . . ?
O4 Zr1 Zr2 90.9(3) 2_665 3_656 ?
O4 Zr1 Zr2 35.37(17) 2_665 11_565 ?
O4 Zr1 Zr2 90.9(3) . 9_666 ?
O4 Zr1 O3 71.3(2) 2_665 . ?
O4 Zr1 O3 71.3(2) . 2_665 ?
O4 Zr1 O3 71.3(2) . . ?
O4 Zr1 O3 71.3(2) 2_665 2_665 ?
O4 Zr1 O4 110.0(7) 2_665 . ?
Zr1 Zr2 Zr1 88.56(3) 9_666 . ?
Zr1 Zr2 Zr2 59.619(19) 9_666 3_656 ?
Zr1 Zr2 Zr2 59.555(16) . 11_565 ?
Zr1 Zr2 Zr2 59.619(19) . 3_656 ?
Zr1 Zr2 Zr2 59.554(16) 9_666 11_565 ?
Zr2 Zr2 Zr2 90.002(1) 3_656 11_565 ?
O2 Zr2 Zr1 71.82(13) 4_566 9_666 ?
O2 Zr2 Zr1 71.82(13) 11_565 . ?
O2 Zr2 Zr1 160.38(14) 11_565 9_666 ?
O2 Zr2 Zr1 160.38(14) 4_566 . ?
O2 Zr2 Zr2 107.93(17) 11_565 3_656 ?
O2 Zr2 Zr2 108.31(15) 11_565 11_565 ?
O2 Zr2 Zr2 107.93(17) 4_566 3_656 ?
O2 Zr2 Zr2 108.31(15) 4_566 11_565 ?
O2 Zr2 O2 127.8(3) 4_566 11_565 ?
O5 Zr2 Zr1 119.44(14) . . ?
O5 Zr2 Zr1 119.44(14) . 9_666 ?
O5 Zr2 Zr2 178.4(2) . 3_656 ?
O5 Zr2 Zr2 88.4(2) . 11_565 ?
O5 Zr2 O2 72.60(19) . 4_566 ?
O5 Zr2 O2 72.60(19) . 11_565 ?
O6 Zr2 Zr1 118.65(19) . . ?
O6 Zr2 Zr1 118.65(19) . 9_666 ?
O6 Zr2 Zr2 87.0(3) . 3_656 ?
O6 Zr2 Zr2 177.0(3) . 11_565 ?
O6 Zr2 O2 72.69(19) . 4_566 ?
O6 Zr2 O2 72.69(19) . 11_565 ?
O6 Zr2 O5 94.6(4) . . ?
O3 Zr2 Zr1 89.4(2) . 9_666 ?
O3 Zr2 Zr1 89.4(2) 10_556 . ?
O3 Zr2 Zr1 37.2(3) . . ?
O3 Zr2 Zr1 37.2(3) 10_556 9_666 ?
O3 Zr2 Zr2 91.7(3) 10_556 3_656 ?
O3 Zr2 Zr2 34.31(18) 10_556 11_565 ?
O3 Zr2 Zr2 91.7(3) . 3_656 ?
O3 Zr2 Zr2 34.31(18) . 11_565 ?
O3 Zr2 O2 75.2(3) 10_556 4_566 ?
O3 Zr2 O2 75.2(3) . 11_565 ?
O3 Zr2 O2 139.1(3) . 4_566 ?
O3 Zr2 O2 139.1(3) 10_556 11_565 ?
O3 Zr2 O5 87.0(4) 10_556 . ?
O3 Zr2 O5 87.0(4) . . ?
O3 Zr2 O6 145.74(17) 10_556 . ?
O3 Zr2 O6 145.74(17) . . ?
O3 Zr2 O3 68.5(3) 10_556 . ?
O4 Zr2 Zr1 88.5(3) 10_556 . ?
O4 Zr2 Zr1 36.0(2) 10_556 9_666 ?
O4 Zr2 Zr1 88.5(3) . 9_666 ?
O4 Zr2 Zr1 36.0(2) . . ?
O4 Zr2 Zr2 90.2(3) 10_556 11_565 ?
O4 Zr2 Zr2 34.1(2) . 3_656 ?
O4 Zr2 Zr2 34.1(2) 10_556 3_656 ?
O4 Zr2 Zr2 90.2(3) . 11_565 ?
O4 Zr2 O2 75.6(3) . 11_565 ?
O4 Zr2 O2 75.6(3) 10_556 4_566 ?
O4 Zr2 O2 139.2(3) . 4_566 ?
O4 Zr2 O2 139.2(3) 10_556 11_565 ?
O4 Zr2 O5 145.9(2) 10_556 . ?
O4 Zr2 O5 145.9(2) . . ?
O4 Zr2 O6 87.3(4) . . ?
O4 Zr2 O6 87.3(4) 10_556 . ?
O4 Zr2 O3 110.0(5) . 10_556 ?
O4 Zr2 O3 110.0(5) 10_556 . ?
O4 Zr2 O3 73.2(4) 10_556 10_556 ?
O4 Zr2 O3 73.2(4) . . ?
O4 Zr2 O4 68.2(5) . 10_556 ?
C1 O1 Zr1 132.7(4) . . ?
C1 O2 Zr2 133.3(5) . 11_565 ?
Zr2 O3 Zr1 106.9(4) 11_565 . ?
Zr2 O3 Zr1 106.9(4) . . ?
Zr2 O3 Zr2 111.4(4) . 11_565 ?
C9 N1 C8 104.6(6) . . ?
C7 C2 C1 118.0(7) . . ?
C3 C2 C1 122.6(7) . . ?
C3 C2 C7 119.3(7) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.5(7) . . ?
C11 C10 C9 119.1(6) 6_665 . ?
C11 C10 C9 119.1(6) . . ?
C11 C10 C11 121.7(12) . 6_665 ?
O1 C1 C2 116.4(6) . . ?
O2 C1 O1 125.7(6) . . ?
O2 C1 C2 117.8(6) . . ?
Zr2 O4 Zr1 108.6(4) 3_656 . ?
Zr2 O4 Zr1 108.6(4) . . ?
Zr2 O4 Zr2 111.8(5) . 3_656 ?
C2 C7 H7 120.3 . . ?
C6 C7 C2 119.4(8) . . ?
C6 C7 H7 120.3 . . ?
C6 C5 C8 118.8(7) . . ?
C6 C5 C4 119.2(7) . . ?
C4 C5 C8 121.7(7) . . ?
N1 C8 C5 117.2(6) . . ?
C8 C8 N1 108.8(4) 6_665 . ?
C8 C8 C5 133.5(4) 6_665 . ?
N1 C9 N1 113.1(8) 6_665 . ?
N1 C9 C10 123.4(4) . . ?
N1 C9 C10 123.4(4) 6_665 . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 122.1(7) . . ?
C4 C3 H3 119.0 . . ?
C5 C4 H4 120.4 . . ?
C3 C4 C5 119.2(7) . . ?
C3 C4 H4 120.4 . . ?
C10 C11 C12 121.5(9) . . ?
C11 C11 C10 119.1(6) 10_557 . ?
C11 C11 C12 119.3(6) 10_557 . ?
C11 C12 H12 119.3 . . ?
C13 C12 C11 121.4(11) . . ?
C13 C12 H12 119.3 . . ?
C12 C13 C13 119.2(8) . 10_557 ?
C12 C13 H13 120.4 . . ?
C13 C13 H13 120.4 10_557 . ?

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
Zr1 O1 C1 O2 -12.1(14) . . . . ?
Zr1 O1 C1 C2 164.1(5) . . . . ?
Zr2 O2 C1 O1 12.1(15) 11_565 . . . ?
Zr2 O2 C1 C2 -164.1(6) 11_565 . . . ?
C2 C3 C4 C5 -2.0(12) . . . . ?
C6 C5 C8 N1 38.2(14) . . . . ?
C6 C5 C8 C8 -151.2(15) . . . 6_665 ?
C6 C5 C4 C3 1.8(12) . . . . ?
C10 C11 C12 C13 -177.8(11) . . . . ?
C1 C2 C7 C6 -177.5(8) . . . . ?
C1 C2 C3 C4 -178.7(8) . . . . ?
C7 C2 C1 O1 -11.4(12) . . . . ?
C7 C2 C1 O2 165.1(9) . . . . ?
C7 C2 C3 C4 -1.7(14) . . . . ?
C7 C6 C5 C8 176.0(9) . . . . ?
C7 C6 C5 C4 1.9(14) . . . . ?
C5 C6 C7 C2 -5.5(14) . . . . ?
C8 N1 C9 N1 -0.7(5) . . . 6_665 ?
C8 N1 C9 C10 179.3(5) . . . . ?
C8 C5 C4 C3 -172.1(9) . . . . ?
C9 N1 C8 C5 174.9(8) . . . . ?
C9 N1 C8 C8 2.1(14) . . . 6_665 ?
C9 C10 C11 C11 180.000(6) . . . 10_557 ?
C9 C10 C11 C12 -0.6(8) . . . . ?
C3 C2 C1 O1 165.6(8) . . . . ?
C3 C2 C1 O2 -17.8(13) . . . . ?
C3 C2 C7 C6 5.4(14) . . . . ?
C4 C5 C8 N1 -147.8(9) . . . . ?
C4 C5 C8 C8 23(2) . . . 6_665 ?
C11 C10 C9 N1 -120.0(6) . . . . ?
C11 C10 C9 N1 -120.0(6) 6_665 . . 6_665 ?
C11 C10 C9 N1 60.0(6) 6_665 . . . ?
C11 C10 C9 N1 60.0(6) . . . 6_665 ?
C11 C10 C11 C11 0.000(9) 6_665 . . 10_557 ?
C11 C10 C11 C12 179.4(8) 6_665 . . . ?
C11 C11 C12 C13 1.5(12) 10_557 . . . ?
C11 C12 C13 C13 -1.5(12) . . . 10_557 ?

loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.230 -0.053 -0.189 5995.6 1866.4 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2235400'
loop_
_audit_author_name
_audit_author_address
'Bao Li'
;Huazhong university of science and technology
China
;
_audit_update_record             
;
2023-01-10 deposited with the CCDC.	2023-07-25 downloaded from the CCDC.
;
_audit_creation_date             2022-12-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_chemical_formula_moiety         'C5.25 H N0.25 O2.5 Zr1.5'
_chemical_formula_sum            'C48 H24 N4 O20 Zr3'
_chemical_formula_weight         1250.370
loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_radius_bond
Zr ? ?
O ? ?
C ? ?
H ? ?
N ? ?

_space_group_crystal_system      orthorhombic
_space_group_IT_number           65
_space_group_name_H-M_alt        'C m m m'
_space_group_name_Hall           -C_2_2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,z
3 x,-y,-z
4 -x,y,-z
5 -x,-y,-z
6 x,y,-z
7 -x,y,z
8 x,-y,z
9 1/2+x,1/2+y,z
10 1/2-x,1/2-y,z
11 1/2+x,1/2-y,-z
12 1/2-x,1/2+y,-z
13 1/2-x,1/2-y,-z
14 1/2+x,1/2+y,-z
15 1/2-x,1/2+y,z
16 1/2+x,1/2-y,z

_symmetry_int_tables_number      65
_cell_length_a                   11.130(5)
_cell_length_b                   27.452(10)
_cell_length_c                   24.900(9)
_cell_angle_alpha                90.000
_cell_angle_beta                 90.000
_cell_angle_gamma                90.000
_cell_volume                     7608.0(50)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    611
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      15.36
_cell_measurement_theta_min      2.81
_exptl_absorpt_correction_T_max  0.7440
_exptl_absorpt_correction_T_min  0.3440
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1333 before and 0.1028 after correction.
The Ratio of minimum to maximum transmission is 0.4624.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_description       needle
_diffrn_reflns_limit_h_max       -100
_diffrn_reflns_limit_h_min       100
_diffrn_reflns_limit_k_max       -100
_diffrn_reflns_limit_k_min       100
_diffrn_reflns_limit_l_max       -100
_diffrn_reflns_limit_l_min       100
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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)'
_refine_ls_R_factor_all          0.227
_olex2_refinement_description    
;
1. Others
 Fixed Sof: Zr1(0.25) Zr2(0.125) O4(0.125) O5(0.0625) O1(0.0625) C10(0.125)
 C9(0.125) O3(0.125) C1(0.0625) C6(0.0625) H6(0.0625) C5(0.0625) C4(0.0625)
 H4(0.0625) C3(0.0625) H3(0.0625) C2(0.0625) C7(0.0625) H7(0.0625) C8(0.0625)
 N1(0.0625) C11(0.0625) C12(0.125) C15(0.125) C13(0.125) C14(0.125) O6(0.125)
 O2(0.125)
 Fixed U12: Zr1(0) O4(-0) O3(-0) C12(0) C15(0) C13(0) C14(0)
 Fixed U13: Zr1(-0) Zr2(-0) O4(0) C10(0) C9(0) C12(0) C15(0) C13(0) C14(0)
 O6(0) O2(-0)
 Fixed U23: Zr1(-0) Zr2(-0) C10(0) C9(0) O3(0) O6(0) O2(-0)
 Fixed Uiso: H6(0.241) H4(0.282) H3(0.382) H7(0.291)
 Fixed X: Zr1(0) O4(0) C10(0.25) C9(0.25) H6(0.1428) H4(0.3424) H3(0.3203)
 H7(0.1206) C12(0.5) C15(0.5) C13(0.5) C14(0.5)
 Fixed Y: Zr1(0.5) C10(0.75) C9(0.75) O3(0.5) H6(0.6418) H4(0.7261) H3(0.6697)
 H7(0.5854)
 Fixed Z: Zr2(0.5) H6(0.2038) H4(0.3009) H3(0.3696) H7(0.2725) O6(0.5) O2(0.5)
;
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_attached_hydrogens
_atom_site_calc_flag
_atom_site_thermal_displace_type
_atom_site_u_iso_or_equiv
Zr1 Zr 0.0000 0.5000 0.5996(2) 1.000 4 l ? d Uani 0.325(10)
Zr2 Zr 0.1669(16) 0.5667(2) 0.5000 1.000 8 q ? d Uani 0.422(10)
O4 O 0.0000 0.5576(16) 0.472(4) 1.000 8 n ? d Uani 0.80(13)
O5 O 0.115(3) 0.4521(7) 0.6450(8) 1.000 16 r ? d Uani 0.32(3)
O1 O 0.228(3) 0.5912(10) 0.4167(9) 1.000 16 r ? d Uani 0.272(14)
C10 C 0.2500 0.7500 0.062(3) 1.000 8 m ? d Uani 0.197(16)
C9 C 0.2500 0.7500 0.119(3) 1.000 8 m ? d Uani 0.237(15)
O3 O 0.157(8) 0.5000 0.5535(18) 1.000 8 o ? d Uani 0.57(8)
C1 C 0.199(4) 0.5848(18) 0.3652(15) 1.000 16 r ? d Uani 0.228(13)
C6 C 0.178(3) 0.6474(10) 0.2370(7) 1.000 16 r ? d Uani 0.201(13)
H6 H 0.1428 0.6418 0.2038 1.000 16 r ? calc Uiso 0.24100
C5 C 0.245(2) 0.6896(8) 0.2455(8) 1.000 16 r ? d Uani 0.222(12)
C4 C 0.298(3) 0.6979(9) 0.2952(10) 1.000 16 r ? d Uani 0.235(15)
H4 H 0.3424 0.7261 0.3009 1.000 16 r ? calc Uiso 0.28200
C3 C 0.285(3) 0.6641(11) 0.3363(8) 1.000 16 r ? d Uani 0.32(3)
H3 H 0.3203 0.6697 0.3696 1.000 16 r ? calc Uiso 0.38200
C2 C 0.218(3) 0.6220(9) 0.3278(8) 1.000 16 r ? d Uani 0.251(16)
C7 C 0.165(3) 0.6136(8) 0.2782(10) 1.000 16 r ? d Uani 0.242(18)
H7 H 0.1206 0.5854 0.2725 1.000 16 r ? calc Uiso 0.29100
C8 C 0.258(4) 0.7227(14) 0.2043(14) 1.000 16 r ? d Uani 0.237(13)
N1 N 0.253(3) 0.7045(13) 0.1478(11) 1.000 16 r ? d Uani 0.226(12)
C11 C 0.357(2) 0.754(2) 0.037(3) 1.000 16 r ? d Uani 0.42(4)
C12 C 0.5000 0.666(2) 0.0322(4) 1.000 8 n ? d Uani 0.39(4)
C15 C 0.5000 0.843(2) 0.0300(4) 1.000 8 n ? d Uani 0.41(4)
C13 C 0.5000 0.723(2) 0.0501(4) 1.000 8 n ? d Uani 0.43(4)
C14 C 0.5000 0.788(2) 0.0503(4) 1.000 8 n ? d Uani 0.43(4)
O6 O 0.122(6) 0.6452(8) 0.5000 1.000 8 q ? d Uani 0.47(7)
O2 O 0.365(2) 0.5502(4) 0.5000 1.000 8 q ? d Uani 0.63(10)


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Zr1 Zr2 . 3_566 3.600(11) no
Zr1 Zr2 . 7 3.600(11) no
Zr1 Zr2 . . 3.600(11) no
Zr1 Zr2 . 5_566 3.600(11) no
Zr1 O4 . 6_556 2.37(5) no
Zr1 O4 . 5_566 2.37(5) no
Zr1 O5 . 2_565 2.15(3) no
Zr1 O5 . 8_565 2.15(3) no
Zr1 O5 . . 2.15(3) no
Zr1 O5 . 7 2.15(3) no
Zr1 O3 . 2_565 2.09(9) no
Zr1 O3 . . 2.09(9) no
Zr2 Zr2 . 3_566 3.664(14) no
Zr2 O4 . 6_556 2.00(3) no
Zr2 O4 . . 2.00(3) no
Zr2 O1 . . 2.28(3) no
Zr2 O1 . 6_556 2.28(3) no
Zr2 O3 . 6_556 2.27(3) no
Zr2 O3 . . 2.27(3) no
Zr2 O6 . . 2.21(2) no
Zr2 O2 . . 2.251(18) no
O4 O4 . 6_556 1.42(18) no
O5 C1 . 3_566 1.40(5) no
O1 C1 . . 1.33(4) no
C10 C9 . . 1.42(2) no
C10 C11 . 10_565 1.34(5) no
C10 C11 . . 1.34(5) no
C9 N1 . 10_565 1.45(4) no
C9 N1 . . 1.45(4) no
C1 C2 . . 1.40(5) no
C6 H6 . . 0.9300 no
C6 C5 . . 1.3900 no
C6 C7 . . 1.3900 no
C5 C4 . . 1.3900 no
C5 C8 . . 1.38(4) no
C4 H4 . . 0.9300 no
C4 C3 . . 1.3900 no
C3 H3 . . 0.9300 no
C3 C2 . . 1.3900 no
C2 C7 . . 1.3900 no
C7 H7 . . 0.9300 no
C8 C8 . 10_565 1.51(8) no
C8 N1 . . 1.49(4) no
C11 C11 . 6 1.87(13) no
C11 C13 . . 1.83(2) no
C11 C14 . . 1.88(2) no
C12 C12 . 6 1.60(2) no
C12 C13 . . 1.61(2) no
C15 C15 . 6 1.49(2) no
C15 C14 . . 1.58(2) no
C13 C14 . . 1.80(2) no

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Zr2 Zr1 Zr2 3_566 . . 61.2(3) no
Zr2 Zr1 Zr2 3_566 . 7 92.9(3) no
Zr2 Zr1 Zr2 . . 7 62.1(5) no
Zr2 Zr1 Zr2 . . 5_566 92.9(3) no
Zr2 Zr1 Zr2 5_566 . 7 61.2(3) no
Zr2 Zr1 Zr2 3_566 . 5_566 62.1(5) no
O4 Zr1 Zr2 5_566 . 5_566 31.5(4) no
O4 Zr1 Zr2 5_566 . 7 79.9(17) no
O4 Zr1 Zr2 6_556 . . 31.5(4) no
O4 Zr1 Zr2 5_566 . 3_566 31.5(4) no
O4 Zr1 Zr2 6_556 . 5_566 79.9(17) no
O4 Zr1 Zr2 5_566 . . 79.9(17) no
O4 Zr1 Zr2 6_556 . 3_566 79.9(17) no
O4 Zr1 Zr2 6_556 . 7 31.5(4) no
O4 Zr1 O4 5_566 . 6_556 83.(4) no
O5 Zr1 Zr2 . . 5_566 110.9(7) no
O5 Zr1 Zr2 2_565 . 5_566 111.5(10) no
O5 Zr1 Zr2 2_565 . 3_566 168.0(6) no
O5 Zr1 Zr2 . . . 111.5(10) no
O5 Zr1 Zr2 7 . 7 111.5(10) no
O5 Zr1 Zr2 2_565 . 7 75.2(7) no
O5 Zr1 Zr2 8_565 . . 75.2(7) no
O5 Zr1 Zr2 . . 7 168.0(6) no
O5 Zr1 Zr2 7 . 3_566 110.9(7) no
O5 Zr1 Zr2 8_565 . 7 110.9(7) no
O5 Zr1 Zr2 2_565 . . 110.9(7) no
O5 Zr1 Zr2 8_565 . 3_566 111.5(10) no
O5 Zr1 Zr2 8_565 . 5_566 168.0(7) no
O5 Zr1 Zr2 . . 3_566 75.2(7) no
O5 Zr1 Zr2 7 . 5_566 75.2(7) no
O5 Zr1 Zr2 7 . . 168.0(6) no
O5 Zr1 O4 . . 5_566 89.1(17) no
O5 Zr1 O4 7 . 5_566 89.1(18) no
O5 Zr1 O4 2_565 . 5_566 142.9(10) no
O5 Zr1 O4 7 . 6_556 142.9(10) no
O5 Zr1 O4 2_565 . 6_556 89.1(17) no
O5 Zr1 O4 . . 6_556 142.9(10) no
O5 Zr1 O4 8_565 . 6_556 89.1(18) no
O5 Zr1 O4 8_565 . 5_566 142.9(10) no
O5 Zr1 O5 8_565 . 2_565 72.8(19) no
O5 Zr1 O5 . . 7 72.8(19) no
O5 Zr1 O5 . . 2_565 116.8(13) no
O5 Zr1 O5 . . 8_565 75.3(14) no
O5 Zr1 O5 8_565 . 7 116.8(13) no
O5 Zr1 O5 7 . 2_565 75.3(14) no
O3 Zr1 Zr2 . . . 35.9(6) no
O3 Zr1 Zr2 2_565 . . 93.0(11) no
O3 Zr1 Zr2 . . 5_566 93.(1) no
O3 Zr1 Zr2 . . 7 93.(1) no
O3 Zr1 Zr2 2_565 . 3_566 93.(1) no
O3 Zr1 Zr2 . . 3_566 35.9(6) no
O3 Zr1 Zr2 2_565 . 7 35.9(6) no
O3 Zr1 Zr2 2_565 . 5_566 35.9(6) no
O3 Zr1 O4 . . 5_566 65.8(12) no
O3 Zr1 O4 . . 6_556 65.8(11) no
O3 Zr1 O4 2_565 . 6_556 65.8(12) no
O3 Zr1 O4 2_565 . 5_566 65.8(12) no
O3 Zr1 O5 2_565 . 7 78.0(12) no
O3 Zr1 O5 2_565 . 8_565 141.6(8) no
O3 Zr1 O5 . . 7 141.6(8) no
O3 Zr1 O5 . . 8_565 78.0(12) no
O3 Zr1 O5 . . 2_565 141.6(8) no
O3 Zr1 O5 2_565 . . 141.6(8) no
O3 Zr1 O5 2_565 . 2_565 78.0(12) no
O3 Zr1 O5 . . . 78.0(12) no
O3 Zr1 O3 2_565 . . 113.(2) no
Zr1 Zr2 Zr1 . . 5_566 87.1(3) no
Zr1 Zr2 Zr2 5_566 . 3_566 59.41(13) no
Zr1 Zr2 Zr2 . . 3_566 59.41(13) no
O4 Zr2 Zr1 . . 5_566 38.2(13) no
O4 Zr2 Zr1 6_556 . . 38.2(13) no
O4 Zr2 Zr1 . . . 73.(3) no
O4 Zr2 Zr1 6_556 . 5_566 73.(3) no
O4 Zr2 Zr2 6_556 . 3_566 82.8(14) no
O4 Zr2 Zr2 . . 3_566 82.8(14) no
O4 Zr2 O4 . . 6_556 41.(5) no
O4 Zr2 O1 6_556 . . 129.(2) no
O4 Zr2 O1 . . 6_556 129.(2) no
O4 Zr2 O1 . . . 90.(3) no
O4 Zr2 O1 6_556 . 6_556 90.(3) no
O4 Zr2 O3 . . . 94.(3) no
O4 Zr2 O3 6_556 . 6_556 94.(3) no
O4 Zr2 O3 6_556 . . 69.(2) no
O4 Zr2 O3 . . 6_556 69.(2) no
O4 Zr2 O6 6_556 . . 85.(2) no
O4 Zr2 O6 . . . 85.(2) no
O4 Zr2 O2 6_556 . . 152.0(13) no
O4 Zr2 O2 . . . 152.0(13) no
O1 Zr2 Zr1 6_556 . . 71.2(7) no
O1 Zr2 Zr1 . . . 158.3(9) no
O1 Zr2 Zr1 6_556 . 5_566 158.3(9) no
O1 Zr2 Zr1 . . 5_566 71.2(7) no
O1 Zr2 Zr2 6_556 . 3_566 107.1(7) no
O1 Zr2 Zr2 . . 3_566 107.1(7) no
O1 Zr2 O1 . . 6_556 130.5(16) no
O3 Zr2 Zr1 . . . 33.(2) no
O3 Zr2 Zr1 6_556 . . 88.2(10) no
O3 Zr2 Zr1 . . 5_566 88.2(10) no
O3 Zr2 Zr1 6_556 . 5_566 33.(2) no
O3 Zr2 Zr2 6_556 . 3_566 36.1(10) no
O3 Zr2 Zr2 . . 3_566 36.1(10) no
O3 Zr2 O1 . . . 141.8(18) no
O3 Zr2 O1 6_556 . 6_556 141.8(18) no
O3 Zr2 O1 . . 6_556 73.7(10) no
O3 Zr2 O1 6_556 . . 73.7(10) no
O3 Zr2 O3 . . 6_556 71.9(17) no
O6 Zr2 Zr1 . . . 112.3(14) no
O6 Zr2 Zr1 . . 5_566 112.3(14) no
O6 Zr2 Zr2 . . 3_566 167.(2) no
O6 Zr2 O1 . . 6_556 77.3(10) no
O6 Zr2 O1 . . . 77.3(10) no
O6 Zr2 O3 . . 6_556 140.9(18) no
O6 Zr2 O3 . . . 140.9(18) no
O6 Zr2 O2 . . . 115.(2) no
O2 Zr2 Zr1 . . 5_566 113.8(3) no
O2 Zr2 Zr1 . . . 113.8(3) no
O2 Zr2 Zr2 . . 3_566 78.4(3) no
O2 Zr2 O1 . . 6_556 76.5(8) no
O2 Zr2 O1 . . . 76.5(8) no
O2 Zr2 O3 . . 6_556 83.(2) no
O2 Zr2 O3 . . . 83.(2) no
Zr2 O4 Zr1 . . 5_566 110.3(12) no
Zr2 O4 Zr1 7 . 5_566 110.3(12) no
Zr2 O4 Zr2 7 . . 136.(4) no
O4 O4 Zr1 6_556 . 5_566 138.(2) no
O4 O4 Zr2 6_556 . . 69.(3) no
O4 O4 Zr2 6_556 . 7 69.(3) no
C1 O5 Zr1 3_566 . . 138.(2) no
C1 O1 Zr2 . . . 140.(3) no
C11 C10 C9 . . . 117.(3) no
C11 C10 C9 10_565 . . 117.(3) no
C11 C10 C11 10_565 . . 127.(7) no
C10 C9 N1 . . 10_565 120.(3) no
C10 C9 N1 . . . 120.(3) no
N1 C9 N1 10_565 . . 120.(5) no
Zr1 O3 Zr2 . . . 111.(3) no
Zr1 O3 Zr2 . . 3_566 111.(3) no
Zr2 O3 Zr2 3_566 . . 108.(2) no
O1 C1 O5 . . 3_566 116.(4) no
O1 C1 C2 . . . 120.(4) no
C2 C1 O5 . . 3_566 120.(3) no
C5 C6 H6 . . . 120.00 no
C5 C6 C7 . . . 120.00 no
C7 C6 H6 . . . 120.00 no
C6 C5 C4 . . . 120.00 no
C8 C5 C6 . . . 119.(3) no
C8 C5 C4 . . . 121.(3) no
C5 C4 H4 . . . 120.00 no
C5 C4 C3 . . . 120.00 no
C3 C4 H4 . . . 120.00 no
C4 C3 H3 . . . 120.00 no
C2 C3 C4 . . . 120.00 no
C2 C3 H3 . . . 120.00 no
C3 C2 C1 . . . 126.(2) no
C7 C2 C1 . . . 114.(2) no
C7 C2 C3 . . . 120.00 no
C6 C7 H7 . . . 120.00 no
C2 C7 C6 . . . 120.00 no
C2 C7 H7 . . . 120.00 no
C5 C8 C8 . . 10_565 130.1(19) no
C5 C8 N1 . . . 119.(3) no
N1 C8 C8 . . 10_565 109.(2) no
C9 N1 C8 . . . 101.(4) no
C10 C11 C11 . . 6 117.(3) no
C10 C11 C13 . . . 131.(4) no
C10 C11 C14 . . . 135.(4) no
C11 C11 C14 6 . . 100.(2) no
C13 C11 C11 . . 6 100.(2) no
C13 C11 C14 . . . 58.2(9) no
C12 C12 C13 6 . . 106.0(6) no
C15 C15 C14 6 . . 108.7(6) no
C11 C13 C11 7_655 . . 121.(2) no
C12 C13 C11 . . 7_655 113.4(11) no
C12 C13 C11 . . . 113.4(11) no
C12 C13 C14 . . . 164.1(9) no
C14 C13 C11 . . . 62.4(9) no
C14 C13 C11 . . 7_655 62.4(9) no
C11 C14 C11 . . 7_655 115.(2) no
C15 C14 C11 . . 7_655 115.3(11) no
C15 C14 C11 . . . 115.3(11) no
C15 C14 C13 . . . 161.2(10) no
C13 C14 C11 . . 7_655 59.4(9) no
C13 C14 C11 . . . 59.4(9) no

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Zr2 O1 C1 O5 . . . 3_566 -10.(7) no
Zr2 O1 C1 C2 . . . . 149.(3) no
O5 C1 C2 C3 3_566 . . . 170.(3) no
O5 C1 C2 C7 3_566 . . . -11.(4) no
O1 C1 C2 C3 . . . . 12.(5) no
O1 C1 C2 C7 . . . . -169.(3) no
C10 C9 N1 C8 . . . . 177.(2) no
C10 C11 C13 C11 . . . 7_655 -148.(3) no
C10 C11 C13 C12 . . . . 72.(5) no
C10 C11 C13 C14 . . . . -125.(6) no
C10 C11 C14 C11 . . . 7_655 140.(4) no
C10 C11 C14 C15 . . . . -82.(5) no
C10 C11 C14 C13 . . . . 119.(5) no
C9 C10 C11 C11 . . . 6 180.00 no
C9 C10 C11 C13 . . . . 45.(5) no
C9 C10 C11 C14 . . . . -39.(5) no
C1 C2 C7 C6 . . . . -179.(2) no
C6 C5 C4 C3 . . . . 0.00 no
C6 C5 C8 C8 . . . 10_565 133.(6) no
C6 C5 C8 N1 . . . . -28.(5) no
C5 C6 C7 C2 . . . . 0.00 no
C5 C4 C3 C2 . . . . 0.00 no
C5 C8 N1 C9 . . . . 171.(3) no
C4 C5 C8 C8 . . . 10_565 -48.(7) no
C4 C5 C8 N1 . . . . 152.(3) no
C4 C3 C2 C1 . . . . 179.(3) no
C4 C3 C2 C7 . . . . 0.00 no
C3 C2 C7 C6 . . . . 0.00 no
C7 C6 C5 C4 . . . . 0.00 no
C7 C6 C5 C8 . . . . 180.(2) no
C8 C5 C4 C3 . . . . -180.(2) no
C8 C8 N1 C9 10_565 . . . 7.(5) no
N1 C9 N1 C8 10_565 . . . -3.(2) no
C11 C10 C9 N1 10_565 . . . 87.(3) no
C11 C10 C9 N1 . . . 10_565 87.(3) no
C11 C10 C9 N1 10_565 . . 10_565 -93.(3) no
C11 C10 C9 N1 . . . . -93.(3) no
C11 C10 C11 C11 10_565 . . 6 0.00 no
C11 C10 C11 C13 10_565 . . . -135.(5) no
C11 C10 C11 C14 10_565 . . . 141.(5) no
C11 C11 C13 C11 6 . . 7_655 72.(3) no
C11 C11 C13 C12 6 . . . -67.6(12) no
C11 C11 C13 C14 6 . . . 95.4(12) no
C11 C11 C14 C11 6 . . 7_655 -74.(3) no
C11 C11 C14 C15 6 . . . 63.8(12) no
C11 C11 C14 C13 6 . . . -95.7(13) no
C11 C13 C14 C11 . . . 7_655 -157.(5) no
C11 C13 C14 C11 7_655 . . . 157.(5) no
C11 C13 C14 C15 7_655 . . . 79.(2) no
C11 C13 C14 C15 . . . . -79.(2) no
C12 C12 C13 C11 6 . . . 71.(2) no
C12 C12 C13 C11 6 . . 7_655 -71.(2) no
C12 C12 C13 C14 6 . . . 0.00(1) no
C12 C13 C14 C11 . . . 7_655 -79.(2) no
C12 C13 C14 C11 . . . . 79.(2) no
C12 C13 C14 C15 . . . . 0.00(7) no
C15 C15 C14 C11 6 . . . -69.(2) no
C15 C15 C14 C11 6 . . 7_655 69.(2) no
C15 C15 C14 C13 6 . . . 0.00(1) no
C13 C11 C14 C11 . . . 7_655 21.(4) no
C13 C11 C14 C15 . . . . 159.5(10) no
C14 C11 C13 C11 . . . 7_655 -23.(4) no
C14 C11 C13 C12 . . . . -163.(1) no

loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.230 -0.053 -0.189 5995.6 1866.4 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p_sx
_database_code_depnum_ccdc_archive 'CCDC 2235396'
loop_
_audit_author_name
_audit_author_address
'Bao Li'
;Huazhong university of science and technology
China
;
_audit_update_record             
;
2023-01-10 deposited with the CCDC.	2023-07-25 downloaded from the CCDC.
;
_audit_creation_date             2022-12-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C48 H24 N4 O20 Zr3'
_chemical_formula_sum            'C48 H24 N4 O20 Zr3'
_chemical_formula_weight         1250.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zr Zr -2.9673 0.5597 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           65
_space_group_name_H-M_alt        'C m m m'
_space_group_name_Hall           '-C 2 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x, y, -z'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z'
'x, -y, z'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'

_cell_length_a                   14.612(6)
_cell_length_b                   26.601(14)
_cell_length_c                   24.698(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     9600(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    358
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      13.73
_cell_measurement_theta_min      2.22
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.363
_exptl_absorpt_correction_T_max  0.7439
_exptl_absorpt_correction_T_min  0.5066
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0995 before and 0.0870 after correction.
The Ratio of minimum to maximum transmission is 0.6810.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    0.865
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2480.0
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1445
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16900
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        15.833
_diffrn_reflns_theta_max         15.833
_diffrn_reflns_theta_min         1.590
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                981
_reflns_number_total             1304
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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)'
_refine_diff_density_max         0.859
_refine_diff_density_min         -0.739
_refine_diff_density_rms         0.115
_refine_ls_extinction_coef       0.00026(17)
_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   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         1304
_refine_ls_number_restraints     259
_refine_ls_R_factor_all          0.1161
_refine_ls_R_factor_gt           0.0982
_refine_ls_restrained_S_all      1.171
_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)+(0.1950P)²+163.2322P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2734
_refine_ls_wR_factor_ref         0.2962
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C1-C2
 1.45 with sigma of 0.02
 C1-C3
 2.45 with sigma of 0.02
 C1-C7
 2.45 with sigma of 0.02
 C3-C5
 2.45 with sigma of 0.02
 C7-C5
 2.45 with sigma of 0.02
 C11-C10
 1.5 with sigma of 0.02
 C11-C11_$1
 1.5 with sigma of 0.02
 N1-N1_$2
 2.4 with sigma of 0.02
 C9-C11
 2.45 with sigma of 0.02
 C11-C11_$2
 2.45 with sigma of 0.02
 C12-C11
 1.45 with sigma of 0.02
 C13_$3-C13_$4
 1.5 with sigma of 0.02
 C13-C12
 1.45 with sigma of 0.02
2. Rigid bond restraints
 Zr02, O4, Zr01
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C2, C7, C6, C5, C4
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C9, C10
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C10, C11
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
O5 \\sim O4 \\sim Zr01 \\sim O1 \\sim O2 \\sim C1 \\sim C2 \\sim C3 \\sim C4
\\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim N1 \\sim C9: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
O5 \\sim Zr02: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 2A
C3 \\sim C2 \\sim C7 \\sim C6 \\sim C5 \\sim C4: within 2A with sigma of 0.04
and sigma for terminal atoms of 0.08 within 2A
N1 \\sim C8 \\sim C9 \\sim C10 \\sim O7 \\sim C11 \\sim C12 \\sim C13: within
2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
Zr01 \\sim Zr02 \\sim O3 \\sim O4 \\sim O6 \\sim O5 \\sim O1 \\sim O2: within
2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(C4) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C5) \\sim
Ueq, Uanis(C10) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C3)
\\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq,
Uanis(C11) \\sim Ueq, Uanis(C8) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(O4) \\sim Ueq, Uanis(O5) \\sim Ueq, Uanis(Zr01) \\sim Ueq, Uanis(O1)
\\sim Ueq, Uanis(O2) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms
of 0.2
Uanis(C9) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C5) \\sim
Ueq, Uanis(C4) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C7)
\\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(Zr01) \\sim Ueq,
Uanis(O4) \\sim Ueq, Uanis(O5) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(C3) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C6) \\sim
Ueq, Uanis(C5) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of
0.002
Uanis(O5) \\sim Ueq, Uanis(O4) \\sim Ueq, Uanis(Zr01) \\sim Ueq, Uanis(O1)
\\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C9) \\sim Ueq: with
sigma of 0.02 and sigma for terminal atoms of 0.01
Uanis(N1) \\sim Ueq, Uanis(C8) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(O6) \\sim Ueq, Uanis(O2) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(Zr01) \\sim Ueq, Uanis(Zr02) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C3(H3), C6(H6), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Zr01 Zr 0.500000 0.500000 0.59905(14) 0.0655(19) Uani 1 4 d S TU P . .
Zr02 Zr 0.3791(2) 0.43339(10) 0.500000 0.0730(17) Uani 1 2 d S TU P . .
O1 O 0.5918(8) 0.5503(4) 0.6446(4) 0.054(4) Uani 1 1 d . U . . .
O5 O 0.3897(11) 0.3496(6) 0.500000 0.065(5) Uani 1 2 d S TU P . .
O6 O 0.2272(12) 0.4378(5) 0.500000 0.064(5) Uani 1 2 d S TU P . .
O2 O 0.6694(9) 0.5935(4) 0.5839(5) 0.070(4) Uani 1 1 d . U . . .
O4 O 0.3762(13) 0.500000 0.5486(6) 0.072(5) Uani 1 2 d S TU P . .
O3 O 0.500000 0.4323(6) 0.5485(7) 0.091(7) Uani 1 2 d S T P . .
N1 N 0.7239(10) 0.7080(4) 0.8541(6) 0.073(5) Uani 1 1 d D U . . .
C4 C 0.6512(12) 0.6536(7) 0.7631(7) 0.053(5) Uani 1 1 d . U . . .
H4 H 0.620448 0.652675 0.796083 0.063 Uiso 1 1 calc R U . . .
C2 C 0.6734(12) 0.6216(7) 0.6747(8) 0.055(5) Uani 1 1 d D U . . .
C7 C 0.7387(12) 0.6552(6) 0.6669(6) 0.062(6) Uani 1 1 d D U . . .
H7 H 0.769715 0.655704 0.633982 0.075 Uiso 1 1 calc R U . . .
C5 C 0.7144(12) 0.6881(6) 0.7570(6) 0.057(5) Uani 1 1 d D U . . .
C10 C 0.750000 0.750000 0.9365(13) 0.131(11) Uani 1 2 d DS TU P . .
C1 C 0.6391(13) 0.5861(7) 0.6327(8) 0.063(6) Uani 1 1 d D U . . .
C9 C 0.750000 0.750000 0.8841(9) 0.090(9) Uani 1 2 d DS TU P . .
C3 C 0.6268(12) 0.6183(6) 0.7245(7) 0.059(6) Uani 1 1 d D U . . .
H3 H 0.582350 0.594046 0.731049 0.071 Uiso 1 1 calc R U . . .
C6 C 0.7608(13) 0.6881(7) 0.7045(7) 0.069(5) Uani 1 1 d . U . . .
H6 H 0.806510 0.711537 0.697609 0.083 Uiso 1 1 calc R U . . .
O7 O 0.823(2) 0.7641(10) 0.9625(9) 0.268(12) Uani 1 1 d . U . . .
C12 C 0.856(2) 0.6747(11) 0.9456(14) 0.246(14) Uani 1 1 d D U . . .
H12 H 0.864884 0.678330 0.908515 0.295 Uiso 1 1 calc R U . . .
C13 C 0.904(3) 0.6341(13) 0.9694(4) 0.265(16) Uani 1 1 d D U . . .
H13 H 0.933000 0.609333 0.949075 0.319 Uiso 1 1 calc R U . . .
C11 C 0.796(2) 0.7115(8) 0.9701(4) 0.204(12) Uani 1 1 d D U . . .
C8 C 0.7364(12) 0.7272(6) 0.7981(7) 0.057(6) Uani 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
Zr01 Zr02 3.499(3) . ?
Zr01 Zr02 3.499(3) 9_666 ?
Zr01 Zr02 3.499(3) 3_656 ?
Zr01 Zr02 3.499(3) 11_565 ?
Zr01 O1 2.203(11) . ?
Zr01 O1 2.203(11) 2_665 ?
Zr01 O1 2.203(11) 11_565 ?
Zr01 O1 2.203(11) 12_655 ?
Zr01 O4 2.197(17) 2_665 ?
Zr01 O4 2.196(17) . ?
Zr01 O3 2.192(16) . ?
Zr01 O3 2.192(16) 2_665 ?
Zr02 Zr02 3.544(6) 11_565 ?
Zr02 Zr02 3.532(7) 3_656 ?
Zr02 O5 2.235(17) . ?
Zr02 O6 2.223(18) . ?
Zr02 O2 2.304(12) 9_666 ?
Zr02 O2 2.304(12) 2_665 ?
Zr02 O4 2.141(9) 10_556 ?
Zr02 O4 2.141(9) . ?
Zr02 O3 2.134(10) . ?
Zr02 O3 2.134(10) 10_556 ?
O1 C1 1.214(18) . ?
O2 C1 1.300(19) . ?
N1 C9 1.394(15) . ?
N1 C8 1.486(19) . ?
C4 H4 0.9300 . ?
C4 C5 1.31(2) . ?
C4 C3 1.384(19) . ?
C2 C7 1.322(19) . ?
C2 C1 1.488(15) . ?
C2 C3 1.41(2) . ?
C7 H7 0.9300 . ?
C7 C6 1.315(19) . ?
C5 C6 1.46(2) . ?
C5 C8 1.49(2) . ?
C10 C9 1.30(3) . ?
C10 O7 1.30(3) . ?
C10 O7 1.30(3) 6_665 ?
C10 C11 1.480(17) 6_665 ?
C10 C11 1.480(17) . ?
C3 H3 0.9300 . ?
C6 H6 0.9300 . ?
O7 C11 1.47(3) . ?
O7 C11 1.87(4) 6_665 ?
C12 H12 0.9300 . ?
C12 C13 1.414(19) . ?
C12 C11 1.449(19) . ?
C13 C13 1.51(2) 10_557 ?
C13 H13 0.9300 . ?
C11 C11 1.48(2) 10_557 ?
C8 C8 1.28(3) 6_665 ?

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
Zr02 Zr01 Zr02 60.62(11) 11_565 9_666 ?
Zr02 Zr01 Zr02 91.28(11) . 9_666 ?
Zr02 Zr01 Zr02 60.85(10) 3_656 9_666 ?
Zr02 Zr01 Zr02 91.28(11) 3_656 11_565 ?
Zr02 Zr01 Zr02 60.85(10) . 11_565 ?
Zr02 Zr01 Zr02 60.63(11) . 3_656 ?
O1 Zr01 Zr02 75.1(3) 12_655 11_565 ?
O1 Zr01 Zr02 110.9(3) 11_565 . ?
O1 Zr01 Zr02 75.1(3) 2_665 . ?
O1 Zr01 Zr02 110.9(3) 2_665 11_565 ?
O1 Zr01 Zr02 110.9(3) 2_665 3_656 ?
O1 Zr01 Zr02 166.4(3) 2_665 9_666 ?
O1 Zr01 Zr02 75.1(3) . 9_666 ?
O1 Zr01 Zr02 110.9(3) 11_565 9_666 ?
O1 Zr01 Zr02 110.9(3) 12_655 9_666 ?
O1 Zr01 Zr02 110.9(3) . 11_565 ?
O1 Zr01 Zr02 75.1(3) 11_565 3_656 ?
O1 Zr01 Zr02 166.4(3) 12_655 3_656 ?
O1 Zr01 Zr02 166.4(3) 11_565 11_565 ?
O1 Zr01 Zr02 110.9(3) . 3_656 ?
O1 Zr01 Zr02 110.9(3) 12_655 . ?
O1 Zr01 Zr02 166.4(3) . . ?
O1 Zr01 O1 75.0(6) . 12_655 ?
O1 Zr01 O1 74.8(6) 2_665 12_655 ?
O1 Zr01 O1 74.8(6) . 11_565 ?
O1 Zr01 O1 118.6(6) . 2_665 ?
O1 Zr01 O1 118.6(6) 12_655 11_565 ?
O1 Zr01 O1 75.0(6) 2_665 11_565 ?
O4 Zr01 Zr02 91.1(4) 2_665 . ?
O4 Zr01 Zr02 91.1(4) 2_665 11_565 ?
O4 Zr01 Zr02 35.7(2) . 11_565 ?
O4 Zr01 Zr02 91.1(4) . 9_666 ?
O4 Zr01 Zr02 35.7(2) 2_665 9_666 ?
O4 Zr01 Zr02 91.1(4) . 3_656 ?
O4 Zr01 Zr02 35.7(2) . . ?
O4 Zr01 Zr02 35.7(2) 2_665 3_656 ?
O4 Zr01 O1 77.8(4) . 2_665 ?
O4 Zr01 O1 77.8(4) 2_665 11_565 ?
O4 Zr01 O1 142.3(3) 2_665 2_665 ?
O4 Zr01 O1 77.8(4) . 12_655 ?
O4 Zr01 O1 142.3(3) . 11_565 ?
O4 Zr01 O1 77.8(4) 2_665 . ?
O4 Zr01 O1 142.3(3) 2_665 12_655 ?
O4 Zr01 O1 142.3(3) . . ?
O4 Zr01 O4 110.9(9) . 2_665 ?
O3 Zr01 Zr02 91.0(4) 2_665 3_656 ?
O3 Zr01 Zr02 35.5(2) 2_665 11_565 ?
O3 Zr01 Zr02 35.5(2) . 3_656 ?
O3 Zr01 Zr02 91.0(4) 2_665 . ?
O3 Zr01 Zr02 35.5(2) 2_665 9_666 ?
O3 Zr01 Zr02 35.5(2) . . ?
O3 Zr01 Zr02 91.0(4) . 11_565 ?
O3 Zr01 Zr02 91.0(4) . 9_666 ?
O3 Zr01 O1 142.2(3) 2_665 11_565 ?
O3 Zr01 O1 142.2(3) 2_665 2_665 ?
O3 Zr01 O1 142.2(3) . 12_655 ?
O3 Zr01 O1 78.0(5) . 2_665 ?
O3 Zr01 O1 78.0(5) 2_665 12_655 ?
O3 Zr01 O1 78.0(5) . 11_565 ?
O3 Zr01 O1 142.2(3) . . ?
O3 Zr01 O1 78.0(5) 2_665 . ?
O3 Zr01 O4 71.1(3) 2_665 2_665 ?
O3 Zr01 O4 71.1(3) . . ?
O3 Zr01 O4 71.1(3) 2_665 . ?
O3 Zr01 O4 71.1(3) . 2_665 ?
O3 Zr01 O3 110.5(10) 2_665 . ?
Zr01 Zr02 Zr01 88.71(11) 9_666 . ?
Zr01 Zr02 Zr02 59.57(5) . 11_565 ?
Zr01 Zr02 Zr02 59.57(5) 9_666 11_565 ?
Zr01 Zr02 Zr02 59.69(6) . 3_656 ?
Zr01 Zr02 Zr02 59.69(6) 9_666 3_656 ?
Zr02 Zr02 Zr02 90.0 3_656 11_565 ?
O5 Zr02 Zr01 118.0(3) . . ?
O5 Zr02 Zr01 118.0(3) . 9_666 ?
O5 Zr02 Zr02 176.0(4) . 11_565 ?
O5 Zr02 Zr02 86.0(4) . 3_656 ?
O5 Zr02 O2 73.2(3) . 2_665 ?
O5 Zr02 O2 73.2(3) . 9_666 ?
O6 Zr02 Zr01 118.5(2) . . ?
O6 Zr02 Zr01 118.5(2) . 9_666 ?
O6 Zr02 Zr02 87.0(4) . 11_565 ?
O6 Zr02 Zr02 177.0(4) . 3_656 ?
O6 Zr02 O5 97.0(6) . . ?
O6 Zr02 O2 73.1(4) . 9_666 ?
O6 Zr02 O2 73.1(4) . 2_665 ?
O2 Zr02 Zr01 160.3(3) 9_666 . ?
O2 Zr02 Zr01 160.3(3) 2_665 9_666 ?
O2 Zr02 Zr01 71.6(3) 9_666 9_666 ?
O2 Zr02 Zr01 71.6(3) 2_665 . ?
O2 Zr02 Zr02 108.1(3) 2_665 11_565 ?
O2 Zr02 Zr02 108.1(3) 9_666 11_565 ?
O2 Zr02 Zr02 107.9(3) 9_666 3_656 ?
O2 Zr02 Zr02 107.9(3) 2_665 3_656 ?
O2 Zr02 O2 128.1(6) 9_666 2_665 ?
O4 Zr02 Zr01 89.0(4) . 9_666 ?
O4 Zr02 Zr01 36.8(5) 10_556 9_666 ?
O4 Zr02 Zr01 36.8(5) . . ?
O4 Zr02 Zr01 89.0(4) 10_556 . ?
O4 Zr02 Zr02 91.2(5) 10_556 3_656 ?
O4 Zr02 Zr02 34.1(3) . 11_565 ?
O4 Zr02 Zr02 91.2(5) . 3_656 ?
O4 Zr02 Zr02 34.1(3) 10_556 11_565 ?
O4 Zr02 O5 145.8(3) 10_556 . ?
O4 Zr02 O5 145.8(3) . . ?
O4 Zr02 O6 86.4(6) 10_556 . ?
O4 Zr02 O6 86.4(6) . . ?
O4 Zr02 O2 139.1(5) 10_556 2_665 ?
O4 Zr02 O2 75.3(5) 10_556 9_666 ?
O4 Zr02 O2 139.1(5) . 9_666 ?
O4 Zr02 O2 75.3(5) . 2_665 ?
O4 Zr02 O4 68.2(7) 10_556 . ?
O3 Zr02 Zr01 88.9(4) 10_556 . ?
O3 Zr02 Zr01 88.9(4) . 9_666 ?
O3 Zr02 Zr01 36.6(4) . . ?
O3 Zr02 Zr01 36.6(4) 10_556 9_666 ?
O3 Zr02 Zr02 90.8(5) 10_556 11_565 ?
O3 Zr02 Zr02 90.8(5) . 11_565 ?
O3 Zr02 Zr02 34.1(4) 10_556 3_656 ?
O3 Zr02 Zr02 34.1(4) . 3_656 ?
O3 Zr02 O5 85.9(6) . . ?
O3 Zr02 O5 85.9(6) 10_556 . ?
O3 Zr02 O6 145.8(4) 10_556 . ?
O3 Zr02 O6 145.8(4) . . ?
O3 Zr02 O2 139.0(5) 10_556 2_665 ?
O3 Zr02 O2 75.3(5) 10_556 9_666 ?
O3 Zr02 O2 75.3(5) . 2_665 ?
O3 Zr02 O2 139.0(5) . 9_666 ?
O3 Zr02 O4 73.3(6) 10_556 10_556 ?
O3 Zr02 O4 110.0(7) 10_556 . ?
O3 Zr02 O4 73.3(6) . . ?
O3 Zr02 O4 110.0(7) . 10_556 ?
O3 Zr02 O3 68.3(8) 10_556 . ?
C1 O1 Zr01 134.4(11) . . ?
C1 O2 Zr02 133.0(11) . 9_666 ?
Zr02 O4 Zr01 107.5(6) 11_565 . ?
Zr02 O4 Zr01 107.5(6) . . ?
Zr02 O4 Zr02 111.7(7) . 11_565 ?
Zr02 O3 Zr01 108.0(5) . . ?
Zr02 O3 Zr01 108.0(5) 3_656 . ?
Zr02 O3 Zr02 111.7(8) 3_656 . ?
C9 N1 C8 100.6(12) . . ?
C5 C4 H4 117.4 . . ?
C5 C4 C3 125.2(18) . . ?
C3 C4 H4 117.4 . . ?
C7 C2 C1 124.7(17) . . ?
C7 C2 C3 121.2(16) . . ?
C3 C2 C1 114.0(15) . . ?
C2 C7 H7 119.2 . . ?
C6 C7 C2 121.5(18) . . ?
C6 C7 H7 119.2 . . ?
C4 C5 C6 115.4(15) . . ?
C4 C5 C8 124.2(16) . . ?
C6 C5 C8 120.4(15) . . ?
C9 C10 O7 119(2) . 6_665 ?
C9 C10 O7 119(2) . . ?
C9 C10 C11 124.1(11) . . ?
C9 C10 C11 124.1(11) . 6_665 ?
O7 C10 O7 121(4) . 6_665 ?
O7 C10 C11 84(2) . 6_665 ?
O7 C10 C11 63.2(17) 6_665 6_665 ?
O7 C10 C11 63.2(17) . . ?
O7 C10 C11 84(2) 6_665 . ?
C11 C10 C11 112(2) 6_665 . ?
O1 C1 O2 122.5(15) . . ?
O1 C1 C2 121.4(17) . . ?
O2 C1 C2 115.8(16) . . ?
N1 C9 N1 115.9(19) . 6_665 ?
C10 C9 N1 122.0(9) . . ?
C10 C9 N1 122.0(9) . 6_665 ?
C4 C3 C2 115.8(16) . . ?
C4 C3 H3 122.1 . . ?
C2 C3 H3 122.1 . . ?
C7 C6 C5 120.9(17) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C10 O7 C11 51.9(15) . 6_665 ?
C10 O7 C11 64.2(16) . . ?
C11 O7 C11 93.7(18) . 6_665 ?
C13 C12 H12 115.0 . . ?
C13 C12 C11 130(3) . . ?
C11 C12 H12 115.0 . . ?
C12 C13 C13 114.6(16) . 10_557 ?
C12 C13 H13 122.7 . . ?
C13 C13 H13 122.7 10_557 . ?
C10 C11 O7 43.9(10) . 6_665 ?
O7 C11 C10 52.6(12) . . ?
O7 C11 O7 84.9(17) . 6_665 ?
O7 C11 C11 97.3(10) . 10_557 ?
C12 C11 C10 120.7(19) . . ?
C12 C11 O7 139(2) . 6_665 ?
C12 C11 O7 115(3) . . ?
C12 C11 C11 114.7(15) . 10_557 ?
C11 C11 C10 124.1(11) 10_557 . ?
C11 C11 O7 95.7(8) 10_557 6_665 ?
N1 C8 C5 111.7(12) . . ?
C8 C8 N1 111.4(7) 6_665 . ?
C8 C8 C5 136.9(9) 6_665 . ?

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
Zr01 O1 C1 O2 -24(3) . . . . ?
Zr01 O1 C1 C2 162.3(11) . . . . ?
Zr02 O2 C1 O1 23(3) 9_666 . . . ?
Zr02 O2 C1 C2 -163.1(11) 9_666 . . . ?
C4 C5 C6 C7 0(3) . . . . ?
C4 C5 C8 N1 33(2) . . . . ?
C4 C5 C8 C8 -147(3) . . . 6_665 ?
C2 C7 C6 C5 1(3) . . . . ?
C7 C2 C1 O1 166.2(18) . . . . ?
C7 C2 C1 O2 -8(3) . . . . ?
C7 C2 C3 C4 2(3) . . . . ?
C5 C4 C3 C2 -1(3) . . . . ?
C10 O7 C11 O7 -33(2) . . . 6_665 ?
C10 O7 C11 C12 111(3) . . . . ?
C10 O7 C11 C11 -127.8(16) . . . 10_557 ?
C1 C2 C7 C6 174.6(18) . . . . ?
C1 C2 C3 C4 -174.7(15) . . . . ?
C9 N1 C8 C5 178.7(13) . . . . ?
C9 N1 C8 C8 -1(2) . . . 6_665 ?
C9 C10 O7 C11 126.1(11) . . . 6_665 ?
C9 C10 O7 C11 -115.8(9) . . . . ?
C9 C10 C11 O7 -121.9(17) . . . 6_665 ?
C9 C10 C11 O7 108.9(18) . . . . ?
C9 C10 C11 C12 9(4) . . . . ?
C9 C10 C11 C11 180.000(19) . . . 10_557 ?
C3 C4 C5 C6 0(3) . . . . ?
C3 C4 C5 C8 176.9(17) . . . . ?
C3 C2 C7 C6 -2(3) . . . . ?
C3 C2 C1 O1 -17(3) . . . . ?
C3 C2 C1 O2 169.0(16) . . . . ?
C6 C5 C8 N1 -150.1(16) . . . . ?
C6 C5 C8 C8 29(4) . . . 6_665 ?
O7 C10 C9 N1 128.1(15) . . . . ?
O7 C10 C9 N1 -51.9(15) . . . 6_665 ?
O7 C10 C9 N1 -51.9(15) 6_665 . . . ?
O7 C10 C9 N1 128.1(15) 6_665 . . 6_665 ?
O7 C10 O7 C11 64.2(9) 6_665 . . . ?
O7 C10 O7 C11 -53.9(11) 6_665 . . 6_665 ?
O7 C10 C11 O7 129(3) . . . 6_665 ?
O7 C10 C11 O7 -129(3) 6_665 . . . ?
O7 C10 C11 C12 -100(4) . . . . ?
O7 C10 C11 C12 131(4) 6_665 . . . ?
O7 C10 C11 C11 71.1(18) . . . 10_557 ?
O7 C10 C11 C11 -58.1(17) 6_665 . . 10_557 ?
C13 C12 C11 C10 -178(4) . . . . ?
C13 C12 C11 O7 123(4) . . . . ?
C13 C12 C11 O7 -124(4) . . . 6_665 ?
C13 C12 C11 C11 11(5) . . . 10_557 ?
C11 C10 C9 N1 -127.9(18) . . . 6_665 ?
C11 C10 C9 N1 52.1(18) . . . . ?
C11 C10 C9 N1 -127.9(18) 6_665 . . . ?
C11 C10 C9 N1 52.1(18) 6_665 . . 6_665 ?
C11 C10 O7 C11 -118.0(16) . . . 6_665 ?
C11 C10 O7 C11 118.0(16) 6_665 . . . ?
C11 C10 C11 O7 58.1(17) 6_665 . . 6_665 ?
C11 C10 C11 O7 -71.1(18) 6_665 . . . ?
C11 C10 C11 C12 -171(4) 6_665 . . . ?
C11 C10 C11 C11 0.000(12) 6_665 . . 10_557 ?
C11 O7 C11 C10 44.1(16) 6_665 . . . ?
C11 O7 C11 O7 11.4(15) 6_665 . . 6_665 ?
C11 O7 C11 C12 155(2) 6_665 . . . ?
C11 O7 C11 C11 -83.7(8) 6_665 . . 10_557 ?
C11 C12 C13 C13 -11(5) . . . 10_557 ?
C8 N1 C9 N1 0.3(8) . . . 6_665 ?
C8 N1 C9 C10 -179.7(8) . . . . ?
C8 C5 C6 C7 -176.6(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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data_p_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2235397'
loop_
_audit_author_name
_audit_author_address
'Bao Li'
;Huazhong university of science and technology
China
;
_audit_update_record             
;
2023-01-10 deposited with the CCDC.	2023-07-25 downloaded from the CCDC.
;
_audit_creation_date             2022-12-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C48 H24 N4 O20 Zr3'
_chemical_formula_sum            'C48 H24 N4 O20 Zr3'
_chemical_formula_weight         1250.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zr Zr -2.9673 0.5597 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           65
_space_group_name_H-M_alt        'C m m m'
_space_group_name_Hall           '-C 2 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x, y, -z'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z'
'x, -y, z'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'

_cell_length_a                   14.117(3)
_cell_length_b                   26.646(6)
_cell_length_c                   24.669(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     9280(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    611
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      15.36
_cell_measurement_theta_min      2.81
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.375
_exptl_absorpt_correction_T_max  0.7440
_exptl_absorpt_correction_T_min  0.3440
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1333 before and 0.1028 after correction.
The Ratio of minimum to maximum transmission is 0.4624.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    0.895
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2480.0
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1731
_diffrn_reflns_av_unetI/netI     0.0706
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            35617
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        20.827
_diffrn_reflns_theta_max         20.827
_diffrn_reflns_theta_min         1.528
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1517
_reflns_number_total             2682
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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)'
_refine_diff_density_max         0.957
_refine_diff_density_min         -0.831
_refine_diff_density_rms         0.128
_refine_ls_extinction_coef       0.0007(3)
_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   1.244
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2682
_refine_ls_number_restraints     100
_refine_ls_R_factor_all          0.1456
_refine_ls_R_factor_gt           0.1097
_refine_ls_restrained_S_all      1.295
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3202
_refine_ls_wR_factor_ref         0.3575
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C12-C10
 2.45 with sigma of 0.02
 C12-C11
 1.45 with sigma of 0.02
 C11-C10
 1.45 with sigma of 0.02
 C12-C13
 1.45 with sigma of 0.02
 C11-C13
 2.45 with sigma of 0.02
 C13_$1-C13_$2
 1.45 with sigma of 0.02
 C11_$3-C11_$4
 1.45 with sigma of 0.02
 O7-C10 \\sim C10-C11
 with sigma of 0.02
2. Rigid bond restraints
 O7, C10, C11, C12, C13
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O7, C10, C11
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C9 \\sim C10 \\sim C11 \\sim C12 \\sim C13: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
O7 \\sim C11 \\sim C10: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
C8 \\sim C5 \\sim N1: within 2A with sigma of 0.04 and sigma for terminal atoms
of 0.08 within 2A
O7 \\sim C10 \\sim C11: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
Uanis(C9) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C8) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C1) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C10) \\sim
Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C6(H6), C13(H13), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Zr01 Zr 0.500000 0.500000 0.40079(8) 0.1060(14) Uani 1 4 d S T P . .
Zr02 Zr 0.6249(2) 0.56634(6) 0.500000 0.1126(13) Uani 1 2 d S T P . .
O1 O 0.4064(7) 0.4500(3) 0.3552(3) 0.088(3) Uani 1 1 d . . . . .
O6 O 0.6120(10) 0.6485(4) 0.500000 0.093(4) Uani 1 2 d S T P . .
O2 O 0.3253(8) 0.4064(3) 0.4172(3) 0.110(4) Uani 1 1 d . . . . .
O5 O 0.7810(11) 0.5644(4) 0.500000 0.108(5) Uani 1 2 d S T P . .
O3 O 0.6269(13) 0.500000 0.4513(4) 0.142(7) Uani 1 2 d S T P . .
N1 N 0.2729(9) 0.2901(3) 0.1451(3) 0.101(4) Uani 1 1 d . U . . .
C1 C 0.3555(10) 0.4137(4) 0.3695(4) 0.079(4) Uani 1 1 d . U . . .
O4 O 0.500000 0.5683(5) 0.4505(5) 0.110(5) Uani 1 2 d S T P . .
C10 C 0.250000 0.250000 0.0603(7) 0.156(7) Uani 1 2 d DS TU P . .
C5 C 0.2800(12) 0.3116(4) 0.2445(4) 0.094(5) Uani 1 1 d . U . . .
C3 C 0.2567(12) 0.3431(5) 0.3333(4) 0.105(5) Uani 1 1 d . . . . .
H3 H 0.224572 0.340683 0.366076 0.126 Uiso 1 1 calc R U . . .
C2 C 0.3207(14) 0.3803(5) 0.3264(4) 0.113(6) Uani 1 1 d . . . . .
C4 C 0.2384(11) 0.3097(4) 0.2940(4) 0.107(5) Uani 1 1 d . U . . .
H4 H 0.195283 0.284097 0.301003 0.128 Uiso 1 1 calc R U . . .
C7 C 0.3677(12) 0.3829(4) 0.2739(4) 0.110(6) Uani 1 1 d . . . . .
H7 H 0.411070 0.408391 0.267049 0.132 Uiso 1 1 calc R U . . .
C9 C 0.250000 0.250000 0.1149(7) 0.075(5) Uani 1 2 d S TU P . .
C6 C 0.3492(12) 0.3494(5) 0.2358(4) 0.110(6) Uani 1 1 d . . . . .
H6 H 0.381839 0.350572 0.203073 0.131 Uiso 1 1 calc R U . . .
C8 C 0.2630(11) 0.2758(5) 0.2021(4) 0.092(4) Uani 1 1 d . U . . .
C11 C 0.300(2) 0.2126(8) 0.0293(4) 0.238(9) Uani 1 1 d D U . . .
C13 C 0.415(2) 0.1425(9) 0.0296(4) 0.300(14) Uani 1 1 d D U . . .
H13 H 0.447306 0.117578 0.048577 0.360 Uiso 1 1 calc R U . . .
C12 C 0.365(2) 0.1808(10) 0.0583(9) 0.297(12) Uani 1 1 d D U . . .
H12 H 0.374916 0.185225 0.095282 0.356 Uiso 1 1 calc R U . . .
O7 O 0.3298(15) 0.2673(8) 0.0338(7) 0.292(9) Uani 1 1 d D U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
Zr01 Zr02 3.496(2) 11_565 ?
Zr01 Zr02 3.496(2) . ?
Zr01 Zr02 3.496(2) 9_666 ?
Zr01 Zr02 3.496(2) 3_656 ?
Zr01 O1 2.188(8) 11_565 ?
Zr01 O1 2.188(8) . ?
Zr01 O1 2.188(8) 2_665 ?
Zr01 O1 2.188(8) 12_655 ?
Zr01 O3 2.182(15) 2_665 ?
Zr01 O3 2.182(15) . ?
Zr01 O4 2.195(11) . ?
Zr01 O4 2.195(11) 2_665 ?
Zr02 Zr02 3.526(6) 3_656 ?
Zr02 Zr02 3.535(3) 11_565 ?
Zr02 O6 2.196(10) . ?
Zr02 O2 2.279(8) 9_666 ?
Zr02 O2 2.279(8) 2_665 ?
Zr02 O5 2.205(16) . ?
Zr02 O3 2.138(6) . ?
Zr02 O3 2.138(6) 10_556 ?
Zr02 O4 2.145(7) . ?
Zr02 O4 2.145(7) 10_556 ?
O1 C1 1.256(14) . ?
O2 C1 1.266(13) . ?
N1 C9 1.342(12) . ?
N1 C8 1.463(14) . ?
C1 C2 1.470(16) . ?
C10 C9 1.35(2) . ?
C10 C11 1.440(12) 6 ?
C10 C11 1.440(12) . ?
C10 O7 1.382(16) . ?
C10 O7 1.382(16) 6 ?
C5 C4 1.356(16) . ?
C5 C6 1.419(17) . ?
C5 C8 1.436(15) . ?
C3 H3 0.9300 . ?
C3 C2 1.350(19) . ?
C3 C4 1.343(16) . ?
C2 C7 1.459(18) . ?
C4 H4 0.9300 . ?
C7 H7 0.9300 . ?
C7 C6 1.322(15) . ?
C6 H6 0.9300 . ?
C8 C8 1.42(2) 6 ?
C11 C11 1.447(18) 10 ?
C11 C12 1.442(16) . ?
C11 O7 1.91(3) 6 ?
C11 O7 1.52(3) . ?
C13 C13 1.462(18) 10 ?
C13 H13 0.9300 . ?
C13 C12 1.427(16) . ?
C12 H12 0.9300 . ?
O7 O7 1.67(4) 10 ?

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
Zr02 Zr01 Zr02 60.56(9) 11_565 9_666 ?
Zr02 Zr01 Zr02 60.56(9) 3_656 . ?
Zr02 Zr01 Zr02 91.14(7) 9_666 . ?
Zr02 Zr01 Zr02 60.74(6) 11_565 . ?
Zr02 Zr01 Zr02 60.74(6) 3_656 9_666 ?
Zr02 Zr01 Zr02 91.13(7) 11_565 3_656 ?
O1 Zr01 Zr02 111.3(2) 11_565 9_666 ?
O1 Zr01 Zr02 110.9(2) . 11_565 ?
O1 Zr01 Zr02 75.4(2) 12_655 11_565 ?
O1 Zr01 Zr02 110.9(2) 12_655 9_666 ?
O1 Zr01 Zr02 166.5(2) 12_655 3_656 ?
O1 Zr01 Zr02 111.3(2) 12_655 . ?
O1 Zr01 Zr02 75.4(2) 2_665 . ?
O1 Zr01 Zr02 166.5(2) . . ?
O1 Zr01 Zr02 110.9(2) 11_565 . ?
O1 Zr01 Zr02 111.3(2) . 3_656 ?
O1 Zr01 Zr02 166.5(2) 2_665 9_666 ?
O1 Zr01 Zr02 75.4(2) 11_565 3_656 ?
O1 Zr01 Zr02 75.4(2) . 9_666 ?
O1 Zr01 Zr02 110.9(2) 2_665 3_656 ?
O1 Zr01 Zr02 166.5(2) 11_565 11_565 ?
O1 Zr01 Zr02 111.3(2) 2_665 11_565 ?
O1 Zr01 O1 74.3(5) 2_665 11_565 ?
O1 Zr01 O1 118.1(4) 12_655 11_565 ?
O1 Zr01 O1 74.3(5) 12_655 . ?
O1 Zr01 O1 118.1(4) 2_665 . ?
O1 Zr01 O1 75.1(4) 2_665 12_655 ?
O1 Zr01 O1 75.1(4) 11_565 . ?
O1 Zr01 O4 77.4(3) 2_665 . ?
O1 Zr01 O4 77.4(3) . 2_665 ?
O1 Zr01 O4 142.4(2) 12_655 . ?
O1 Zr01 O4 77.4(3) 12_655 2_665 ?
O1 Zr01 O4 142.4(2) 11_565 2_665 ?
O1 Zr01 O4 77.4(3) 11_565 . ?
O1 Zr01 O4 142.4(2) 2_665 2_665 ?
O1 Zr01 O4 142.4(2) . . ?
O3 Zr01 Zr02 90.8(4) 2_665 11_565 ?
O3 Zr01 Zr02 35.6(2) . 11_565 ?
O3 Zr01 Zr02 90.8(4) 2_665 . ?
O3 Zr01 Zr02 35.6(2) . . ?
O3 Zr01 Zr02 90.8(4) . 9_666 ?
O3 Zr01 Zr02 35.6(2) 2_665 9_666 ?
O3 Zr01 Zr02 35.6(2) 2_665 3_656 ?
O3 Zr01 Zr02 90.8(4) . 3_656 ?
O3 Zr01 O1 142.1(2) 2_665 2_665 ?
O3 Zr01 O1 142.1(2) . 11_565 ?
O3 Zr01 O1 142.1(2) . . ?
O3 Zr01 O1 142.1(2) 2_665 12_655 ?
O3 Zr01 O1 78.3(4) . 12_655 ?
O3 Zr01 O1 78.3(4) 2_665 . ?
O3 Zr01 O1 78.3(4) . 2_665 ?
O3 Zr01 O1 78.3(4) 2_665 11_565 ?
O3 Zr01 O3 110.4(8) 2_665 . ?
O3 Zr01 O4 71.4(3) . 2_665 ?
O3 Zr01 O4 71.4(3) . . ?
O3 Zr01 O4 71.4(3) 2_665 . ?
O3 Zr01 O4 71.4(3) 2_665 2_665 ?
O4 Zr01 Zr02 35.87(19) 2_665 11_565 ?
O4 Zr01 Zr02 91.6(3) . 11_565 ?
O4 Zr01 Zr02 35.87(19) . . ?
O4 Zr01 Zr02 91.6(3) . 9_666 ?
O4 Zr01 Zr02 35.87(19) . 3_656 ?
O4 Zr01 Zr02 91.6(3) 2_665 3_656 ?
O4 Zr01 Zr02 35.87(19) 2_665 9_666 ?
O4 Zr01 Zr02 91.6(3) 2_665 . ?
O4 Zr01 O4 112.1(7) 2_665 . ?
Zr01 Zr02 Zr01 88.87(7) . 9_666 ?
Zr01 Zr02 Zr02 59.72(4) . 3_656 ?
Zr01 Zr02 Zr02 59.72(4) 9_666 3_656 ?
Zr01 Zr02 Zr02 59.63(3) . 11_565 ?
Zr01 Zr02 Zr02 59.63(3) 9_666 11_565 ?
Zr02 Zr02 Zr02 89.999(1) 3_656 11_565 ?
O6 Zr02 Zr01 117.5(2) . . ?
O6 Zr02 Zr01 117.5(2) . 9_666 ?
O6 Zr02 Zr02 175.3(4) . 11_565 ?
O6 Zr02 Zr02 85.3(4) . 3_656 ?
O6 Zr02 O2 73.0(2) . 2_665 ?
O6 Zr02 O2 73.0(2) . 9_666 ?
O6 Zr02 O5 96.1(5) . . ?
O2 Zr02 Zr01 71.9(2) 2_665 . ?
O2 Zr02 Zr01 71.9(2) 9_666 9_666 ?
O2 Zr02 Zr01 160.7(2) 2_665 9_666 ?
O2 Zr02 Zr01 160.7(2) 9_666 . ?
O2 Zr02 Zr02 108.56(19) 9_666 11_565 ?
O2 Zr02 Zr02 108.0(3) 9_666 3_656 ?
O2 Zr02 Zr02 108.56(19) 2_665 11_565 ?
O2 Zr02 Zr02 108.0(3) 2_665 3_656 ?
O2 Zr02 O2 127.4(4) 9_666 2_665 ?
O5 Zr02 Zr01 119.48(19) . 9_666 ?
O5 Zr02 Zr01 119.48(19) . . ?
O5 Zr02 Zr02 178.6(3) . 3_656 ?
O5 Zr02 Zr02 88.6(3) . 11_565 ?
O5 Zr02 O2 72.5(3) . 2_665 ?
O5 Zr02 O2 72.5(3) . 9_666 ?
O3 Zr02 Zr01 89.0(4) 10_556 . ?
O3 Zr02 Zr01 36.4(4) . . ?
O3 Zr02 Zr01 36.4(4) 10_556 9_666 ?
O3 Zr02 Zr01 89.0(4) . 9_666 ?
O3 Zr02 Zr02 34.2(2) . 11_565 ?
O3 Zr02 Zr02 34.2(2) 10_556 11_565 ?
O3 Zr02 Zr02 90.8(5) 10_556 3_656 ?
O3 Zr02 Zr02 90.8(5) . 3_656 ?
O3 Zr02 O6 145.6(2) 10_556 . ?
O3 Zr02 O6 145.6(2) . . ?
O3 Zr02 O2 75.8(4) . 2_665 ?
O3 Zr02 O2 139.7(4) 10_556 2_665 ?
O3 Zr02 O2 139.7(4) . 9_666 ?
O3 Zr02 O2 75.8(4) 10_556 9_666 ?
O3 Zr02 O5 88.1(6) 10_556 . ?
O3 Zr02 O5 88.1(6) . . ?
O3 Zr02 O3 68.4(5) 10_556 . ?
O3 Zr02 O4 73.2(5) 10_556 10_556 ?
O3 Zr02 O4 110.6(6) 10_556 . ?
O3 Zr02 O4 110.6(6) . 10_556 ?
O3 Zr02 O4 73.2(5) . . ?
O4 Zr02 Zr01 89.8(3) 10_556 . ?
O4 Zr02 Zr01 36.8(3) 10_556 9_666 ?
O4 Zr02 Zr01 36.8(3) . . ?
O4 Zr02 Zr01 89.8(3) . 9_666 ?
O4 Zr02 Zr02 34.7(3) 10_556 3_656 ?
O4 Zr02 Zr02 34.7(3) . 3_656 ?
O4 Zr02 Zr02 91.4(4) 10_556 11_565 ?
O4 Zr02 Zr02 91.4(4) . 11_565 ?
O4 Zr02 O6 84.7(5) 10_556 . ?
O4 Zr02 O6 84.7(5) . . ?
O4 Zr02 O2 139.1(4) 10_556 2_665 ?
O4 Zr02 O2 74.6(4) . 2_665 ?
O4 Zr02 O2 74.6(4) 10_556 9_666 ?
O4 Zr02 O2 139.1(4) . 9_666 ?
O4 Zr02 O5 145.3(3) 10_556 . ?
O4 Zr02 O5 145.3(3) . . ?
O4 Zr02 O4 69.4(5) . 10_556 ?
C1 O1 Zr01 132.1(6) . . ?
C1 O2 Zr02 132.9(9) . 9_666 ?
Zr02 O3 Zr01 108.0(6) . . ?
Zr02 O3 Zr01 108.0(6) 11_565 . ?
Zr02 O3 Zr02 111.5(5) 11_565 . ?
C9 N1 C8 107.7(10) . . ?
O1 C1 O2 124.8(9) . . ?
O1 C1 C2 117.1(10) . . ?
O2 C1 C2 117.9(12) . . ?
Zr02 O4 Zr01 107.3(4) 3_656 . ?
Zr02 O4 Zr01 107.3(4) . . ?
Zr02 O4 Zr02 110.5(5) . 3_656 ?
C9 C10 C11 122.0(8) . . ?
C9 C10 C11 122.0(8) . 6 ?
C9 C10 O7 118.3(12) . 6 ?
C9 C10 O7 118.3(12) . . ?
C11 C10 C11 115.9(16) . 6 ?
O7 C10 C11 65.1(14) . . ?
O7 C10 C11 85.3(15) . 6 ?
O7 C10 C11 65.1(14) 6 6 ?
O7 C10 C11 85.3(15) 6 . ?
O7 C10 O7 123(2) . 6 ?
C4 C5 C6 117.4(10) . . ?
C4 C5 C8 124.0(12) . . ?
C6 C5 C8 118.5(11) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C4 C3 C2 121.7(12) . . ?
C3 C2 C1 125.2(11) . . ?
C3 C2 C7 116.8(11) . . ?
C7 C2 C1 117.5(15) . . ?
C5 C4 H4 118.6 . . ?
C3 C4 C5 122.8(13) . . ?
C3 C4 H4 118.6 . . ?
C2 C7 H7 119.7 . . ?
C6 C7 C2 120.6(13) . . ?
C6 C7 H7 119.7 . . ?
N1 C9 N1 112.5(14) . 6 ?
N1 C9 C10 123.8(7) . . ?
N1 C9 C10 123.8(7) 6 . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.5(12) . . ?
C7 C6 H6 119.7 . . ?
C5 C8 N1 120.7(10) . . ?
C8 C8 N1 106.0(6) 6 . ?
C8 C8 C5 133.3(7) 6 . ?
C10 C11 C11 122.0(8) . 10 ?
C10 C11 C12 117.2(12) . . ?
C10 C11 O7 46.0(8) . 6 ?
C10 C11 O7 55.6(8) . . ?
C11 C11 O7 94.1(8) 10 . ?
C11 C11 O7 93.3(6) 10 6 ?
C12 C11 C11 119.7(9) . 10 ?
C12 C11 O7 138(2) . 6 ?
C12 C11 O7 111(3) . . ?
O7 C11 O7 89.6(10) . 6 ?
C13 C13 H13 120.2 10 . ?
C12 C13 C13 119.7(10) . 10 ?
C12 C13 H13 120.2 . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.3(17) . . ?
C13 C12 H12 120.3 . . ?
C10 O7 C11 48.6(9) . 6 ?
C10 O7 C11 59.3(9) . . ?
C10 O7 O7 118.3(12) . 10 ?
C11 O7 C11 90.0(11) . 6 ?
C11 O7 O7 85.9(8) . 10 ?
O7 O7 C11 86.7(6) 10 6 ?

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
Zr01 O1 C1 O2 22(2) . . . . ?
Zr01 O1 C1 C2 -164.6(10) . . . . ?
Zr02 O2 C1 O1 -22(2) 9_666 . . . ?
Zr02 O2 C1 C2 164.9(9) 9_666 . . . ?
O1 C1 C2 C3 -171.9(14) . . . . ?
O1 C1 C2 C7 17(2) . . . . ?
O2 C1 C2 C3 2(2) . . . . ?
O2 C1 C2 C7 -169.4(12) . . . . ?
C1 C2 C7 C6 170.5(14) . . . . ?
C10 C11 C12 C13 179(3) . . . . ?
C10 C11 O7 C11 -39.8(10) . . . 6 ?
C10 C11 O7 O7 -126.5(10) . . . 10 ?
C3 C2 C7 C6 -2(2) . . . . ?
C2 C3 C4 C5 -2(3) . . . . ?
C2 C7 C6 C5 3(2) . . . . ?
C4 C5 C6 C7 -4(2) . . . . ?
C4 C5 C8 N1 152.2(15) . . . . ?
C4 C5 C8 C8 -28(3) . . . 6 ?
C4 C3 C2 C1 -170.4(14) . . . . ?
C4 C3 C2 C7 1(2) . . . . ?
C9 N1 C8 C5 -178.0(12) . . . . ?
C9 N1 C8 C8 2(2) . . . 6 ?
C9 C10 C11 C11 179.996(5) . . . 10 ?
C9 C10 C11 C12 -12(4) . . . . ?
C9 C10 C11 O7 120.7(12) . . . 6 ?
C9 C10 C11 O7 -109.0(12) . . . . ?
C9 C10 O7 C11 114.5(9) . . . . ?
C9 C10 O7 C11 -124.1(9) . . . 6 ?
C9 C10 O7 O7 180.002(2) . . . 10 ?
C6 C5 C4 C3 3(2) . . . . ?
C6 C5 C8 N1 -32(2) . . . . ?
C6 C5 C8 C8 147(2) . . . 6 ?
C8 N1 C9 N1 -0.9(7) . . . 6 ?
C8 N1 C9 C10 179.1(8) . . . . ?
C8 C5 C4 C3 178.7(15) . . . . ?
C8 C5 C6 C7 -179.4(15) . . . . ?
C11 C10 C9 N1 -52.2(18) 6 . . . ?
C11 C10 C9 N1 127.8(18) . . . . ?
C11 C10 C9 N1 127.8(18) 6 . . 6 ?
C11 C10 C9 N1 -52.2(18) . . . 6 ?
C11 C10 C11 C11 -0.004(5) 6 . . 10 ?
C11 C10 C11 C12 168(4) 6 . . . ?
C11 C10 C11 O7 71.0(12) 6 . . . ?
C11 C10 C11 O7 -59.3(12) 6 . . 6 ?
C11 C10 O7 C11 121.4(13) . . . 6 ?
C11 C10 O7 C11 -121.4(13) 6 . . . ?
C11 C10 O7 O7 -55.9(9) 6 . . 10 ?
C11 C10 O7 O7 65.5(9) . . . 10 ?
C11 C11 C12 C13 -13(4) 10 . . . ?
C11 C11 O7 C10 126.5(10) 10 . . . ?
C11 C11 O7 C11 86.7(6) 10 . . 6 ?
C11 C11 O7 O7 -0.001(2) 10 . . 10 ?
C13 C13 C12 C11 13(4) 10 . . . ?
C12 C11 O7 C10 -109.5(16) . . . . ?
C12 C11 O7 C11 -149.4(15) . . . 6 ?
C12 C11 O7 O7 123.9(15) . . . 10 ?
O7 C10 C9 N1 51.0(13) . . . . ?
O7 C10 C9 N1 -129.0(13) . . . 6 ?
O7 C10 C9 N1 50.9(13) 6 . . 6 ?
O7 C10 C9 N1 -129.1(13) 6 . . . ?
O7 C10 C11 C11 -71.0(12) . . . 10 ?
O7 C10 C11 C11 59.3(12) 6 . . 10 ?
O7 C10 C11 C12 97(3) . . . . ?
O7 C10 C11 C12 -132(3) 6 . . . ?
O7 C10 C11 O7 130(2) 6 . . . ?
O7 C10 C11 O7 -130(2) . . . 6 ?
O7 C10 O7 C11 -65.5(9) 6 . . . ?
O7 C10 O7 C11 55.9(9) 6 . . 6 ?
O7 C10 O7 O7 0.005(3) 6 . . 10 ?
O7 C11 C12 C13 -120(3) . . . . ?
O7 C11 C12 C13 125(3) 6 . . . ?
O7 C11 O7 C10 33.3(13) 6 . . . ?
O7 C11 O7 C11 -6.5(12) 6 . . 6 ?
O7 C11 O7 O7 -93.3(7) 6 . . 10 ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.230 -0.053 -0.189 5995.6 1866.4 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2235399'
loop_
_audit_author_name
_audit_author_address
'Bao Li'
;Huazhong university of science and technology
China
;
_audit_update_record             
;
2023-01-10 deposited with the CCDC.	2023-07-25 downloaded from the CCDC.
;
_audit_creation_date             2022-12-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C48 H24 N4 O20 Zr3'
_chemical_formula_sum            'C48 H24 N4 O20 Zr3'
_chemical_formula_weight         1250.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zr Zr -2.9673 0.5597 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           65
_space_group_name_H-M_alt        'C m m m'
_space_group_name_Hall           '-C 2 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x, y, -z'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z'
'x, -y, z'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'

_cell_length_a                   13.994(10)
_cell_length_b                   26.939(17)
_cell_length_c                   24.532(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     9248(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    611
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      15.36
_cell_measurement_theta_min      2.81
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.377
_exptl_absorpt_correction_T_max  0.7440
_exptl_absorpt_correction_T_min  0.3440
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1333 before and 0.1028 after correction.
The Ratio of minimum to maximum transmission is 0.4624.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
# end Validation Reply Form
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    0.898
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2480.0
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2546
_diffrn_reflns_av_unetI/netI     0.1799
_diffrn_reflns_Laue_measured_fraction_full 0.914
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            22018
_diffrn_reflns_point_group_measured_fraction_full 0.914
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        17.991
_diffrn_reflns_theta_max         17.991
_diffrn_reflns_theta_min         1.512
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.914
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                922
_reflns_number_total             1651
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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)'
_refine_diff_density_max         1.867
_refine_diff_density_min         -0.906
_refine_diff_density_rms         0.181
_refine_ls_extinction_coef       0.0004(2)
_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   1.264
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         1651
_refine_ls_number_restraints     303
_refine_ls_R_factor_all          0.2060
_refine_ls_R_factor_gt           0.1577
_refine_ls_restrained_S_all      2.077
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3470
_refine_ls_wR_factor_ref         0.4023
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 O7-C10
 1.5 with sigma of 0.02
 C9-O7
 2.45 with sigma of 0.02
 O7_$1-O7_$2
 2.45 with sigma of 0.02
 C11-O7
 1.5 with sigma of 0.02
 O2-C2
 2.45 with sigma of 0.02
 C2-O1
 2.45 with sigma of 0.02
 C7-C3
 2.45 with sigma of 0.02
 C1-C7
 2.45 with sigma of 0.02
 C7-C6
 1.45 with sigma of 0.02
 C11_$3-C11
 1.5 with sigma of 0.02
 C10_$4-C11_$3
 1.45 with sigma of 0.02
 C10-O7
 2.45 with sigma of 0.02
 C9-C10
 1.45 with sigma of 0.02
 C11-C12
 1.45 with sigma of 0.02
 C12-C13
 1.45 with sigma of 0.02
 C10-C12
 2.45 with sigma of 0.02
 O7_$3-O7
 1.4 with sigma of 0.02
 C13-C11
 2.5 with sigma of 0.02
 C12_$5-C12_$6
 2.6 with sigma of 0.02
 C11-C13 = C13_$5-C13
 1.5 with sigma of 0.02
 C11-C10
 1.5 with sigma of 0.02
 C11_$3-C10_$3
 1.45 with sigma of 0.02
 C12-O7
 2 with sigma of 0.02
 C14-C14_$5
 1.5 with sigma of 0.02
 C14-C13_$5
 2.2 with sigma of 0.02
2. Restrained planarity
 C6, C7, C2, C3, C4, C5
 with sigma of 0.1
3. Rigid bond restraints
 C1, C2, O1, O2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O7, C10, C11
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C9, C10
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C14 \\sim C13 \\sim C12 \\sim C11 \\sim O7 \\sim C10: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
C9 \\sim N1 \\sim C5 \\sim C6 \\sim C7 \\sim C2 \\sim C3 \\sim C1 \\sim O2
\\sim O1: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
within 2A
C1 \\sim O1 \\sim C2 \\sim O2: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
C9 \\sim N1 \\sim C8 \\sim C10 \\sim O7 \\sim C11 \\sim C14 \\sim C13 \\sim
C12: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C14 \\sim C13 \\sim C12 \\sim C11 \\sim O7 \\sim C10 \\sim C9 \\sim N1 \\sim C8
\\sim C5 \\sim C4 \\sim C3 \\sim C2 \\sim C7 \\sim C6: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(C14) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C11)
\\sim Ueq, Uanis(O7) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C9) \\sim Ueq,
Uanis(N1) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C4) \\sim
Ueq, Uanis(C3) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C6)
\\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(O3) \\sim Ueq,
Uanis(O1) \\sim Ueq, Uanis(O5) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(C9) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim
Ueq, Uanis(C7) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C1)
\\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(O2) \\sim Ueq: with sigma of 0.025 and
sigma for terminal atoms of 0.02
Uanis(C8) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(O1) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.002
Uanis(C4) \\sim Ueq, Uanis(N1) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.002
Uanis(C2) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(Zr01) \\sim Ueq, Uanis(O4) \\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(Zr02)
\\sim Ueq, Uanis(O5) \\sim Ueq, Uanis(O6) \\sim Ueq: with sigma of 11 and sigma
for terminal atoms of 22
5. Others
 Fixed Sof: H14A(0.5) H14B(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
6.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C4(H4), C3(H3), C6(H6), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Zr01 Zr 0.500000 0.500000 0.09983(14) 0.083(2) Uani 1 4 d S TU P . .
Zr02 Zr 0.3743(3) 0.43429(11) 0.000000 0.089(2) Uani 1 2 d S TU P . .
O5 O 0.225(2) 0.4379(8) 0.000000 0.106(10) Uani 1 2 d S TU P . .
O1 O 0.5956(10) 0.5494(5) 0.1443(5) 0.057(4) Uani 1 1 d D U . . .
O6 O 0.3875(15) 0.3545(5) 0.000000 0.073(7) Uani 1 2 d S TU P . .
O2 O 0.6777(11) 0.5922(5) 0.0827(6) 0.078(4) Uani 1 1 d D U . . .
O3 O 0.3742(18) 0.500000 0.0475(5) 0.097(9) Uani 1 2 d S TU P . .
C7 C 0.7423(12) 0.6562(6) 0.1641(7) 0.077(7) Uani 1 1 d D U . . .
H7 H 0.770979 0.656240 0.129854 0.092 Uiso 1 1 calc R U . . .
O4 O 0.500000 0.4338(8) 0.0518(8) 0.091(8) Uani 1 2 d S TU P . .
C10 C 0.750000 0.750000 0.4335(8) 0.217(13) Uani 1 2 d DS TU P . .
N1 N 0.7286(13) 0.7079(6) 0.3518(7) 0.076(5) Uani 1 1 d . U . . .
C4 C 0.6499(15) 0.6532(9) 0.2669(10) 0.074(7) Uani 1 1 d . U . . .
H4 H 0.618899 0.653505 0.300395 0.089 Uiso 1 1 calc R U . . .
C2 C 0.6769(13) 0.6222(6) 0.1762(7) 0.053(5) Uani 1 1 d D U . . .
C5 C 0.7163(16) 0.6863(8) 0.2547(9) 0.070(6) Uani 1 1 d . U . . .
C3 C 0.6282(14) 0.6179(7) 0.2273(8) 0.061(6) Uani 1 1 d D U . . .
H3 H 0.584196 0.592719 0.233737 0.074 Uiso 1 1 calc R U . . .
C6 C 0.7683(16) 0.6922(8) 0.2029(9) 0.094(7) Uani 1 1 d D U . . .
H6 H 0.813178 0.717003 0.196594 0.112 Uiso 1 1 calc R U . . .
C1 C 0.6516(16) 0.5834(8) 0.1329(10) 0.076(6) Uani 1 1 d D U . . .
C8 C 0.7375(16) 0.7264(8) 0.2968(9) 0.072(6) Uani 1 1 d . U . . .
C9 C 0.750000 0.750000 0.3812(8) 0.135(12) Uani 1 2 d DS TU P . .
C11 C 0.6544(8) 0.7481(11) 0.4678(4) 0.264(15) Uani 1 1 d D U . . .
O7 O 0.7127(17) 0.7953(5) 0.4736(4) 0.289(14) Uani 1 1 d D U . . .
C13 C 0.500000 0.7538(19) 0.4691(4) 0.25(2) Uani 1 2 d DS TU P . .
C12 C 0.5823(12) 0.7803(14) 0.4468(4) 0.297(17) Uani 1 1 d D U . . .
H12 H 0.586345 0.808856 0.425629 0.357 Uiso 1 1 calc R U . . .
C14 C 0.500000 0.6955(18) 0.4696(4) 0.20(2) Uani 1 2 d DS TU P . .
H14A H 0.442929 0.680994 0.453802 0.242 Uiso 0.5 1 calc R U P . .
H14B H 0.557071 0.680994 0.453802 0.242 Uiso 0.5 1 calc R U P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
Zr01 Zr02 3.496(4) . ?
Zr01 Zr02 3.496(4) 9_665 ?
Zr01 Zr02 3.496(4) 11_565 ?
Zr01 Zr02 3.496(4) 3_655 ?
Zr01 O1 2.179(12) 12_655 ?
Zr01 O1 2.179(12) 11_565 ?
Zr01 O1 2.179(12) . ?
Zr01 O1 2.179(12) 2_665 ?
Zr01 O3 2.18(2) . ?
Zr01 O3 2.18(2) 2_665 ?
Zr01 O4 2.137(18) . ?
Zr01 O4 2.138(18) 2_665 ?
Zr02 Zr02 3.518(10) 3_655 ?
Zr02 Zr02 3.540(6) 11_565 ?
Zr02 O5 2.09(3) . ?
Zr02 O6 2.158(15) . ?
Zr02 O2 2.271(14) 9_665 ?
Zr02 O2 2.271(14) 2_665 ?
Zr02 O3 2.119(7) 10 ?
Zr02 O3 2.119(7) . ?
Zr02 O4 2.171(12) . ?
Zr02 O4 2.171(12) 10 ?
O1 C1 1.24(2) . ?
O2 C1 1.31(3) . ?
C7 H7 0.9300 . ?
C7 C2 1.33(2) . ?
C7 C6 1.407(17) . ?
C10 C9 1.283(17) . ?
C10 C11 1.581(10) . ?
C10 C11 1.581(10) 6_665 ?
C10 O7 1.653(11) . ?
C10 O7 1.653(11) 6_665 ?
N1 C8 1.44(3) . ?
N1 C9 1.378(19) . ?
C4 H4 0.9300 . ?
C4 C5 1.32(3) . ?
C4 C3 1.39(3) . ?
C2 C3 1.43(2) . ?
C2 C1 1.53(2) . ?
C5 C6 1.47(3) . ?
C5 C8 1.53(3) . ?
C3 H3 0.9300 . ?
C6 H6 0.9300 . ?
C8 C8 1.32(4) 6_665 ?
C11 C11 1.58(2) 10_556 ?
C11 O7 1.518(19) . ?
C11 C12 1.426(18) . ?
O7 O7 1.294(19) 10_556 ?
C13 C13 1.51(2) 3_656 ?
C13 C12 1.462(19) 12_655 ?
C13 C12 1.462(19) . ?
C13 C14 1.57(3) . ?
C12 H12 0.9300 . ?
C14 C14 1.49(2) 3_656 ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?

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
Zr02 Zr01 Zr02 60.41(15) 11_565 9_665 ?
Zr02 Zr01 Zr02 60.83(11) . 11_565 ?
Zr02 Zr01 Zr02 91.08(13) 3_655 11_565 ?
Zr02 Zr01 Zr02 60.83(11) 3_655 9_665 ?
Zr02 Zr01 Zr02 60.41(15) . 3_655 ?
Zr02 Zr01 Zr02 91.08(13) . 9_665 ?
O1 Zr01 Zr02 74.5(4) . 9_665 ?
O1 Zr01 Zr02 110.6(4) 11_565 9_665 ?
O1 Zr01 Zr02 74.5(4) 11_565 3_655 ?
O1 Zr01 Zr02 165.6(4) . . ?
O1 Zr01 Zr02 74.5(4) 12_655 11_565 ?
O1 Zr01 Zr02 110.5(4) 2_665 3_655 ?
O1 Zr01 Zr02 110.5(4) 12_655 9_665 ?
O1 Zr01 Zr02 110.5(4) 11_565 . ?
O1 Zr01 Zr02 165.6(4) 11_565 11_565 ?
O1 Zr01 Zr02 110.6(4) . 3_655 ?
O1 Zr01 Zr02 110.6(4) 2_665 11_565 ?
O1 Zr01 Zr02 110.5(4) . 11_565 ?
O1 Zr01 Zr02 165.6(4) 2_665 9_665 ?
O1 Zr01 Zr02 110.6(4) 12_655 . ?
O1 Zr01 Zr02 74.5(4) 2_665 . ?
O1 Zr01 Zr02 165.6(4) 12_655 3_655 ?
O1 Zr01 O1 75.7(7) 2_665 11_565 ?
O1 Zr01 O1 119.9(7) 12_655 11_565 ?
O1 Zr01 O1 75.2(7) 2_665 12_655 ?
O1 Zr01 O1 119.9(7) . 2_665 ?
O1 Zr01 O1 75.7(7) . 12_655 ?
O1 Zr01 O1 75.2(7) . 11_565 ?
O1 Zr01 O3 78.4(5) 11_565 2_665 ?
O1 Zr01 O3 142.3(4) 11_565 . ?
O1 Zr01 O3 78.4(5) 12_655 . ?
O1 Zr01 O3 78.4(5) 2_665 . ?
O1 Zr01 O3 142.3(3) 2_665 2_665 ?
O1 Zr01 O3 78.4(5) . 2_665 ?
O1 Zr01 O3 142.3(3) . . ?
O1 Zr01 O3 142.3(4) 12_655 2_665 ?
O3 Zr01 Zr02 35.0(3) . . ?
O3 Zr01 Zr02 89.6(5) 2_665 . ?
O3 Zr01 Zr02 35.0(3) . 11_565 ?
O3 Zr01 Zr02 89.6(5) 2_665 11_565 ?
O3 Zr01 Zr02 89.6(5) . 9_665 ?
O3 Zr01 Zr02 89.6(5) . 3_655 ?
O3 Zr01 Zr02 35.0(3) 2_665 3_655 ?
O3 Zr01 Zr02 35.0(3) 2_665 9_665 ?
O3 Zr01 O3 107.8(11) . 2_665 ?
O4 Zr01 Zr02 36.1(3) 2_665 9_665 ?
O4 Zr01 Zr02 36.1(3) 2_665 11_565 ?
O4 Zr01 Zr02 92.1(5) 2_665 3_655 ?
O4 Zr01 Zr02 92.1(5) . 9_665 ?
O4 Zr01 Zr02 92.1(5) . 11_565 ?
O4 Zr01 Zr02 36.1(3) . . ?
O4 Zr01 Zr02 92.1(5) 2_665 . ?
O4 Zr01 Zr02 36.1(3) . 3_655 ?
O4 Zr01 O1 141.7(4) 2_665 2_665 ?
O4 Zr01 O1 141.7(4) . . ?
O4 Zr01 O1 76.5(6) 2_665 12_655 ?
O4 Zr01 O1 76.5(6) . 11_565 ?
O4 Zr01 O1 141.7(4) . 12_655 ?
O4 Zr01 O1 141.7(4) 2_665 11_565 ?
O4 Zr01 O1 76.5(6) 2_665 . ?
O4 Zr01 O1 76.5(6) . 2_665 ?
O4 Zr01 O3 71.1(4) . 2_665 ?
O4 Zr01 O3 71.1(4) 2_665 . ?
O4 Zr01 O3 71.1(4) . . ?
O4 Zr01 O3 71.1(4) 2_665 2_665 ?
O4 Zr01 O4 113.2(12) . 2_665 ?
Zr01 Zr02 Zr01 88.92(13) . 9_665 ?
Zr01 Zr02 Zr02 59.59(6) . 11_565 ?
Zr01 Zr02 Zr02 59.59(6) 9_665 11_565 ?
Zr01 Zr02 Zr02 59.79(8) 9_665 3_655 ?
Zr01 Zr02 Zr02 59.79(8) . 3_655 ?
Zr02 Zr02 Zr02 90.0 3_655 11_565 ?
O5 Zr02 Zr01 118.6(4) . 9_665 ?
O5 Zr02 Zr01 118.6(4) . . ?
O5 Zr02 Zr02 177.3(6) . 3_655 ?
O5 Zr02 Zr02 87.3(6) . 11_565 ?
O5 Zr02 O6 97.6(8) . . ?
O5 Zr02 O2 72.2(5) . 2_665 ?
O5 Zr02 O2 72.2(5) . 9_665 ?
O5 Zr02 O3 87.7(9) . . ?
O5 Zr02 O3 87.7(9) . 10 ?
O5 Zr02 O4 144.1(4) . . ?
O5 Zr02 O4 144.1(4) . 10 ?
O6 Zr02 Zr01 117.5(4) . . ?
O6 Zr02 Zr01 117.5(4) . 9_665 ?
O6 Zr02 Zr02 175.1(6) . 11_565 ?
O6 Zr02 Zr02 85.1(6) . 3_655 ?
O6 Zr02 O2 73.4(4) . 9_665 ?
O6 Zr02 O2 73.4(4) . 2_665 ?
O6 Zr02 O4 85.6(7) . . ?
O6 Zr02 O4 85.6(7) . 10 ?
O2 Zr02 Zr01 72.2(4) 9_665 9_665 ?
O2 Zr02 Zr01 72.2(4) 2_665 . ?
O2 Zr02 Zr01 161.1(4) 2_665 9_665 ?
O2 Zr02 Zr01 161.1(4) 9_665 . ?
O2 Zr02 Zr02 108.3(4) 2_665 11_565 ?
O2 Zr02 Zr02 108.7(4) 2_665 3_655 ?
O2 Zr02 Zr02 108.3(4) 9_665 11_565 ?
O2 Zr02 Zr02 108.7(4) 9_665 3_655 ?
O2 Zr02 O2 126.6(8) 9_665 2_665 ?
O3 Zr02 Zr01 36.2(6) 10 9_665 ?
O3 Zr02 Zr01 36.2(6) . . ?
O3 Zr02 Zr01 87.8(5) . 9_665 ?
O3 Zr02 Zr01 87.8(5) 10 . ?
O3 Zr02 Zr02 90.1(7) . 3_655 ?
O3 Zr02 Zr02 90.1(7) 10 3_655 ?
O3 Zr02 Zr02 33.3(3) 10 11_565 ?
O3 Zr02 Zr02 33.3(3) . 11_565 ?
O3 Zr02 O6 146.3(3) 10 . ?
O3 Zr02 O6 146.3(3) . . ?
O3 Zr02 O2 76.8(5) . 2_665 ?
O3 Zr02 O2 138.9(6) . 9_665 ?
O3 Zr02 O2 138.9(6) 10 2_665 ?
O3 Zr02 O2 76.8(5) 10 9_665 ?
O3 Zr02 O3 66.7(6) . 10 ?
O3 Zr02 O4 71.6(8) . . ?
O3 Zr02 O4 109.2(9) 10 . ?
O3 Zr02 O4 71.6(8) 10 10 ?
O3 Zr02 O4 109.2(9) . 10 ?
O4 Zr02 Zr01 35.4(5) 10 9_665 ?
O4 Zr02 Zr01 90.3(5) . 9_665 ?
O4 Zr02 Zr01 90.3(5) 10 . ?
O4 Zr02 Zr01 35.4(5) . . ?
O4 Zr02 Zr02 90.4(6) . 11_565 ?
O4 Zr02 Zr02 35.9(4) . 3_655 ?
O4 Zr02 Zr02 35.9(4) 10 3_655 ?
O4 Zr02 Zr02 90.4(6) 10 11_565 ?
O4 Zr02 O2 74.6(6) . 2_665 ?
O4 Zr02 O2 74.6(6) 10 9_665 ?
O4 Zr02 O2 141.4(6) 10 2_665 ?
O4 Zr02 O2 141.4(6) . 9_665 ?
O4 Zr02 O4 71.7(8) 10 . ?
C1 O1 Zr01 136.6(13) . . ?
C1 O2 Zr02 134.0(13) . 9_665 ?
Zr02 O3 Zr01 108.9(8) . . ?
Zr02 O3 Zr01 108.9(8) 11_565 . ?
Zr02 O3 Zr02 113.3(6) . 11_565 ?
C2 C7 H7 120.0 . . ?
C2 C7 C6 120.0(18) . . ?
C6 C7 H7 120.0 . . ?
Zr01 O4 Zr02 108.5(7) . 3_655 ?
Zr01 O4 Zr02 108.5(7) . . ?
Zr02 O4 Zr02 108.3(8) 3_655 . ?
C9 C10 C11 122.2(8) . . ?
C9 C10 C11 122.2(8) . 6_665 ?
C9 C10 O7 126.5(6) . 6_665 ?
C9 C10 O7 126.5(6) . . ?
C11 C10 C11 115.7(15) . 6_665 ?
C11 C10 O7 85.8(11) . 6_665 ?
C11 C10 O7 55.9(8) 6_665 6_665 ?
C11 C10 O7 85.8(11) 6_665 . ?
C11 C10 O7 55.9(8) . . ?
O7 C10 O7 106.9(12) . 6_665 ?
C9 N1 C8 100.6(16) . . ?
C5 C4 H4 121.4 . . ?
C5 C4 C3 117(2) . . ?
C3 C4 H4 121.4 . . ?
C7 C2 C3 125.5(15) . . ?
C7 C2 C1 118.2(17) . . ?
C3 C2 C1 116.3(16) . . ?
C4 C5 C6 128(2) . . ?
C4 C5 C8 117(2) . . ?
C6 C5 C8 114.3(18) . . ?
C4 C3 C2 116.9(17) . . ?
C4 C3 H3 121.6 . . ?
C2 C3 H3 121.6 . . ?
C7 C6 C5 112(2) . . ?
C7 C6 H6 123.8 . . ?
C5 C6 H6 123.8 . . ?
O1 C1 O2 121.7(18) . . ?
O1 C1 C2 120(2) . . ?
O2 C1 C2 117.7(17) . . ?
N1 C8 C5 111.8(17) . . ?
C8 C8 N1 110.9(11) 6_665 . ?
C8 C8 C5 137.3(11) 6_665 . ?
C10 C9 N1 121.5(10) . . ?
C10 C9 N1 121.5(10) . 6_665 ?
N1 C9 N1 117(2) . 6_665 ?
C11 C11 C10 122.2(8) 10_556 . ?
O7 C11 C10 64.4(7) . . ?
O7 C11 C11 84.6(5) . 10_556 ?
C12 C11 C10 112.7(11) . . ?
C12 C11 C11 111.2(6) . 10_556 ?
C12 C11 O7 84.6(14) . . ?
C11 O7 C10 59.6(5) . . ?
O7 O7 C10 126.5(6) 10_556 . ?
O7 O7 C11 95.4(5) 10_556 . ?
C13 C13 C14 89.6(5) 3_656 . ?
C12 C13 C13 112.1(7) . 3_656 ?
C12 C13 C13 112.1(7) 12_655 3_656 ?
C12 C13 C12 104(2) . 12_655 ?
C12 C13 C14 119.4(15) 12_655 . ?
C12 C13 C14 119.4(15) . . ?
C11 C12 C13 97.2(14) . . ?
C11 C12 H12 131.4 . . ?
C13 C12 H12 131.4 . . ?
C13 C14 H14A 113.6 . . ?
C13 C14 H14B 113.6 . . ?
C14 C14 C13 90.4(5) 3_656 . ?
C14 C14 H14A 113.6 3_656 . ?
C14 C14 H14B 113.6 3_656 . ?
H14A C14 H14B 110.8 . . ?

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
Zr01 O1 C1 O2 -12(4) . . . . ?
Zr01 O1 C1 C2 156.3(13) . . . . ?
Zr02 O2 C1 O1 12(4) 9_665 . . . ?
Zr02 O2 C1 C2 -156.8(13) 9_665 . . . ?
C7 C2 C3 C4 2(3) . . . . ?
C7 C2 C1 O1 175.4(18) . . . . ?
C7 C2 C1 O2 -16(3) . . . . ?
C10 C11 O7 O7 -129.6(7) . . . 10_556 ?
C10 C11 C12 C13 155.6(16) . . . . ?
C4 C5 C6 C7 -2(3) . . . . ?
C4 C5 C8 N1 35(3) . . . . ?
C4 C5 C8 C8 -146(4) . . . 6_665 ?
C2 C7 C6 C5 0.4(16) . . . . ?
C5 C4 C3 C2 -3(3) . . . . ?
C3 C4 C5 C6 3(4) . . . . ?
C3 C4 C5 C8 177(2) . . . . ?
C3 C2 C1 O1 -4(3) . . . . ?
C3 C2 C1 O2 165.2(19) . . . . ?
C6 C7 C2 C3 -0.5(18) . . . . ?
C6 C7 C2 C1 -179.4(18) . . . . ?
C6 C5 C8 N1 -150.1(18) . . . . ?
C6 C5 C8 C8 29(5) . . . 6_665 ?
C1 C2 C3 C4 -179.4(19) . . . . ?
C8 N1 C9 C10 179.7(10) . . . . ?
C8 N1 C9 N1 -0.3(10) . . . 6_665 ?
C8 C5 C6 C7 -176.4(17) . . . . ?
C9 C10 C11 C11 180.000(2) . . . 10_556 ?
C9 C10 C11 O7 -115.1(6) . . . . ?
C9 C10 C11 C12 -43.4(17) . . . . ?
C9 C10 O7 C11 107.4(8) . . . . ?
C9 C10 O7 O7 180.000(13) . . . 10_556 ?
C9 N1 C8 C5 -179.6(16) . . . . ?
C9 N1 C8 C8 1(3) . . . 6_665 ?
C11 C10 C9 N1 -73.0(16) . . . . ?
C11 C10 C9 N1 107.0(16) . . . 6_665 ?
C11 C10 C9 N1 107.0(16) 6_665 . . . ?
C11 C10 C9 N1 -73.0(16) 6_665 . . 6_665 ?
C11 C10 C11 C11 0.003(2) 6_665 . . 10_556 ?
C11 C10 C11 O7 64.9(6) 6_665 . . . ?
C11 C10 C11 C12 136.6(17) 6_665 . . . ?
C11 C10 O7 C11 -125.1(11) 6_665 . . . ?
C11 C10 O7 O7 -52.4(7) 6_665 . . 10_556 ?
C11 C10 O7 O7 72.6(8) . . . 10_556 ?
C11 C11 O7 C10 129.6(7) 10_556 . . . ?
C11 C11 O7 O7 0.000(5) 10_556 . . 10_556 ?
C11 C11 C12 C13 -63.0(13) 10_556 . . . ?
O7 C10 C9 N1 -142.0(14) . . . . ?
O7 C10 C9 N1 37.9(14) 6_665 . . . ?
O7 C10 C9 N1 -142.0(14) 6_665 . . 6_665 ?
O7 C10 C9 N1 38.0(14) . . . 6_665 ?
O7 C10 C11 C11 48.8(6) 6_665 . . 10_556 ?
O7 C10 C11 C11 -64.9(6) . . . 10_556 ?
O7 C10 C11 O7 113.7(9) 6_665 . . . ?
O7 C10 C11 C12 71.7(16) . . . . ?
O7 C10 C11 C12 -174.6(16) 6_665 . . . ?
O7 C10 O7 C11 -72.6(8) 6_665 . . . ?
O7 C10 O7 O7 0.002(6) 6_665 . . 10_556 ?
O7 C11 C12 C13 -145.0(13) . . . . ?
C13 C13 C12 C11 63.6(12) 3_656 . . . ?
C13 C13 C14 C14 0.000(16) 3_656 . . 3_656 ?
C12 C11 O7 C10 -118.4(9) . . . . ?
C12 C11 O7 O7 112.0(6) . . . 10_556 ?
C12 C13 C12 C11 -175.2(14) 12_655 . . . ?
C12 C13 C14 C14 115.3(9) . . . 3_656 ?
C12 C13 C14 C14 -115.3(9) 12_655 . . 3_656 ?
C14 C13 C12 C11 -39.1(14) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.230 -0.053 -0.189 5995.6 1866.4 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT020_p                   
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.255 Report
RESPONSE: The crystallinity of the crystals has been damaged to some extent
 after one hour at room temperature, under light conditions. This has resulted
 in poor diffraction quality, including the detection of diffraction points at
 high angles and high Ueq factors in the central clusters of Zr and O atoms. 
;
_vrf_PLAT023_p                   
;
PROBLEM: Resolution (too) Low [sin(theta)/Lambda < 0.6]..       0.43 Ang-1
RESPONSE: The crystallinity of the crystals has been damaged to some extent
 after one hour at room temperature, under light conditions. This has resulted
 in poor diffraction quality, including the detection of diffraction points at
 high angles and high Ueq factors in the central clusters of Zr and O atoms. 
;
_vrf_PLAT029_p                   
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.914 Why?
RESPONSE: The crystallinity of the crystals has been damaged to some extent
 after one hour at room temperature, under light conditions. This has resulted
 in poor diffraction quality, including the detection of diffraction points at
 high angles and high Ueq factors in the central clusters of Zr and O atoms. 
;
_vrf_PLAT211_p                   
;
PROBLEM: ADP of Atom Zr01      is N.P.D. or (nearly) 2D .     Please Check
RESPONSE: The crystallinity of the crystals has been damaged to some extent
 after one hour at room temperature, under light conditions. This has resulted
 in poor diffraction quality, including the detection of diffraction points at
 high angles and high Ueq factors in the central clusters of Zr and O atoms. 
;
_vrf_PLAT699_p                   
;
PROBLEM: Missing _exptl_crystal_description Value .......     Please Do !
RESPONSE: The crystallinity of the crystals has been damaged to some extent
 after one hour at room temperature, under light conditions. This has resulted
 in poor diffraction quality, including the detection of diffraction points at
 high angles and high Ueq factors in the central clusters of Zr and O atoms. 
;
_vrf_PLAT973_p                   
;
PROBLEM: Check Calcd Positive Resid. Density on      Zr01       2.34 eA-3
RESPONSE: The crystallinity of the crystals has been damaged to some extent
 after one hour at room temperature, under light conditions. This has resulted
 in poor diffraction quality, including the detection of diffraction points at
 high angles and high Ueq factors in the central clusters of Zr and O atoms. 
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2235395'
loop_
_audit_author_name
_audit_author_address
'Bao Li'
;Huazhong university of science and technology
China
;
_audit_update_record             
;
2023-01-10 deposited with the CCDC.	2023-07-25 downloaded from the CCDC.
;
_audit_creation_date             2022-11-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C48 H24 N4 O16 Zr3'
_chemical_formula_sum            'C48 H24 N4 O16 Zr3'
_chemical_formula_weight         1186.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zr Zr -2.9673 0.5597 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           65
_space_group_name_H-M_alt        'C m m m'
_space_group_name_Hall           '-C 2 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x, y, -z'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z'
'x, -y, z'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'

_cell_length_a                   15.726(9)
_cell_length_b                   25.601(14)
_cell_length_c                   24.817(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     9991(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    611
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      15.36
_cell_measurement_theta_min      2.81
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.343
_exptl_absorpt_correction_T_max  0.7440
_exptl_absorpt_correction_T_min  0.3440
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1333 before and 0.1028 after correction.
The Ratio of minimum to maximum transmission is 0.4624.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    0.789
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2352.0
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1850
_diffrn_reflns_av_unetI/netI     0.0843
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25605
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        17.997
_diffrn_reflns_theta_max         17.997
_diffrn_reflns_theta_min         1.520
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1152
_reflns_number_total             1905
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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)'
_refine_diff_density_max         0.960
_refine_diff_density_min         -1.342
_refine_diff_density_rms         0.128
_refine_ls_extinction_coef       0.0002(2)
_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   1.264
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1905
_refine_ls_number_restraints     212
_refine_ls_R_factor_all          0.1495
_refine_ls_R_factor_gt           0.1143
_refine_ls_restrained_S_all      1.368
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3148
_refine_ls_wR_factor_ref         0.3506
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C11_$1-C11
 1.45 with sigma of 0.02
 C7-C2
 1.45 with sigma of 0.02
 C2-C4
 2.45 with sigma of 0.02
 C7-C3
 2.45 with sigma of 0.02
 C9-C10
 1.45 with sigma of 0.02
 C11-C10
 1.45 with sigma of 0.02
 C11_$1-C12_$1
 1.45 with sigma of 0.02
 C12_$1-C13_$1
 1.45 with sigma of 0.02
 C13_$1-C13
 1.45 with sigma of 0.02
 O4-Zr01 \\sim Zr02-O3
 with sigma of 0.02
2. Rigid bond restraints
 C1, C3, C4, C5, C6, C2, C7
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C13, C12, C11, C10, C9
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O1, O2, C1, O3, O4, Zr02
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
O4 \\sim Zr01 \\sim O3 \\sim Zr02: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
C1 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C2 \\sim C7: within 2A with sigma
of 0.04 and sigma for terminal atoms of 0.08 within 2A
C13 \\sim C12 \\sim C11 \\sim C10 \\sim C9 \\sim N1 \\sim C8: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
O1 \\sim C1 \\sim O2 \\sim Zr01 \\sim O3 \\sim O4 \\sim Zr02: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(O4) \\sim Ueq, Uanis(O3) \\sim Ueq: with sigma of 0.015 and sigma for
terminal atoms of 0.02
Uanis(C1) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C4) \\sim
Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim Ueq: with sigma of 0.025 and sigma
for terminal atoms of 0.1
Uanis(C8) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C13) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C1) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C6) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O1) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(Zr01) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.1
4.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C4(H4), C7(H7), C13(H13), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Zr01 Zr 0.500000 0.500000 0.40185(10) 0.0767(16) Uani 1 4 d DS TU P . .
Zr02 Zr 0.6123(2) 0.56907(9) 0.500000 0.0877(15) Uani 1 2 d DS TU P . .
O1 O 0.4158(7) 0.4471(4) 0.3571(3) 0.063(3) Uani 1 1 d . U . . .
O2 O 0.3421(7) 0.4071(4) 0.4172(4) 0.079(3) Uani 1 1 d . U . . .
O3 O 0.6134(9) 0.500000 0.4525(4) 0.065(4) Uani 1 2 d DS TU P . .
O4 O 0.500000 0.5685(5) 0.4518(6) 0.083(5) Uani 1 2 d DS TU P . .
O6 O 0.6032(10) 0.6543(5) 0.500000 0.088(5) Uani 1 2 d S T P . .
O5 O 0.7569(15) 0.5675(8) 0.500000 0.134(8) Uani 1 2 d S T P . .
C2 C 0.3385(10) 0.3778(6) 0.3277(5) 0.071(5) Uani 1 1 d D U . . .
C1 C 0.3646(11) 0.4134(7) 0.3681(6) 0.063(4) Uani 1 1 d . U . . .
C6 C 0.3582(10) 0.3438(6) 0.2375(5) 0.057(4) Uani 1 1 d . U . . .
H6 H 0.391364 0.340697 0.206637 0.069 Uiso 1 1 calc R U . . .
C3 C 0.2676(10) 0.3482(7) 0.3315(5) 0.079(5) Uani 1 1 d D U . . .
H3 H 0.233331 0.351962 0.361773 0.094 Uiso 1 1 calc R U . . .
N1 N 0.2763(11) 0.2903(5) 0.1463(5) 0.103(5) Uani 1 1 d . U . . .
C5 C 0.2862(12) 0.3115(6) 0.2427(6) 0.072(5) Uani 1 1 d . U . . .
C4 C 0.2427(10) 0.3113(6) 0.2912(5) 0.076(5) Uani 1 1 d D U . . .
H4 H 0.198664 0.287772 0.297415 0.091 Uiso 1 1 calc R U . . .
C7 C 0.3811(10) 0.3784(6) 0.2744(5) 0.080(5) Uani 1 1 d D U . . .
H7 H 0.423363 0.402738 0.266939 0.096 Uiso 1 1 calc R U . . .
C8 C 0.2648(11) 0.2751(6) 0.1983(6) 0.072(5) Uani 1 1 d . U . . .
C10 C 0.250000 0.250000 0.0566(9) 0.124(8) Uani 1 2 d DS TU P . .
C9 C 0.250000 0.250000 0.1150(9) 0.095(7) Uani 1 2 d DS TU P . .
C11 C 0.2970(16) 0.2111(9) 0.0284(4) 0.173(9) Uani 1 1 d D U . . .
C13 C 0.3989(18) 0.1357(12) 0.0297(4) 0.222(12) Uani 1 1 d D U . . .
H13 H 0.429054 0.110551 0.048834 0.267 Uiso 1 1 calc R U . . .
C12 C 0.3511(17) 0.1757(10) 0.0576(11) 0.199(10) Uani 1 1 d . U . . .
H12 H 0.355338 0.178572 0.094906 0.239 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
Zr01 Zr02 3.489(3) 3_656 ?
Zr01 Zr02 3.489(3) 11_565 ?
Zr01 Zr02 3.489(3) 9_666 ?
Zr01 Zr02 3.489(3) . ?
Zr01 O1 2.195(10) 2_665 ?
Zr01 O1 2.195(10) 11_565 ?
Zr01 O1 2.195(10) 12_655 ?
Zr01 O1 2.195(10) . ?
Zr01 O3 2.182(12) 2_665 ?
Zr01 O3 2.182(13) . ?
Zr01 O4 2.147(11) . ?
Zr01 O4 2.147(11) 2_665 ?
Zr02 Zr02 3.531(7) 3_656 ?
Zr02 Zr02 3.536(5) 11_565 ?
Zr02 O2 2.262(10) 9_666 ?
Zr02 O2 2.262(10) 2_665 ?
Zr02 O3 2.125(6) 10_556 ?
Zr02 O3 2.125(6) . ?
Zr02 O4 2.133(8) . ?
Zr02 O4 2.133(8) 10_556 ?
Zr02 O6 2.186(13) . ?
Zr02 O5 2.28(2) . ?
O1 C1 1.212(16) . ?
O2 C1 1.278(17) . ?
C2 C1 1.42(2) . ?
C2 C3 1.353(17) . ?
C2 C7 1.482(14) . ?
C6 H6 0.9300 . ?
C6 C5 1.408(19) . ?
C6 C7 1.322(18) . ?
C3 H3 0.9300 . ?
C3 C4 1.430(19) . ?
N1 C8 1.360(17) . ?
N1 C9 1.356(16) . ?
C5 C4 1.385(19) . ?
C5 C8 1.483(19) . ?
C4 H4 0.9300 . ?
C7 H7 0.9300 . ?
C8 C8 1.36(3) 6 ?
C10 C9 1.449(18) . ?
C10 C11 1.424(15) 6 ?
C10 C11 1.424(15) . ?
C11 C11 1.410(18) 10 ?
C11 C12 1.439(17) . ?
C13 C13 1.47(2) 10 ?
C13 H13 0.9300 . ?
C13 C12 1.448(18) . ?
C12 H12 0.9300 . ?

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
Zr02 Zr01 Zr02 91.46(9) 3_656 11_565 ?
Zr02 Zr01 Zr02 91.46(9) 9_666 . ?
Zr02 Zr01 Zr02 60.78(11) 3_656 . ?
Zr02 Zr01 Zr02 60.78(11) 11_565 9_666 ?
Zr02 Zr01 Zr02 60.89(9) 3_656 9_666 ?
Zr02 Zr01 Zr02 60.89(9) 11_565 . ?
O1 Zr01 Zr02 74.6(3) 12_655 11_565 ?
O1 Zr01 Zr02 111.1(3) 11_565 9_666 ?
O1 Zr01 Zr02 111.1(3) . 3_656 ?
O1 Zr01 Zr02 111.1(3) 12_655 . ?
O1 Zr01 Zr02 166.1(3) 2_665 9_666 ?
O1 Zr01 Zr02 166.1(3) . . ?
O1 Zr01 Zr02 166.1(3) 12_655 3_656 ?
O1 Zr01 Zr02 110.2(3) . 11_565 ?
O1 Zr01 Zr02 74.6(3) 11_565 3_656 ?
O1 Zr01 Zr02 74.6(3) 2_665 . ?
O1 Zr01 Zr02 74.6(3) . 9_666 ?
O1 Zr01 Zr02 166.1(3) 11_565 11_565 ?
O1 Zr01 Zr02 110.2(3) 12_655 9_666 ?
O1 Zr01 Zr02 110.2(3) 2_665 3_656 ?
O1 Zr01 Zr02 110.2(3) 11_565 . ?
O1 Zr01 Zr02 111.1(3) 2_665 11_565 ?
O1 Zr01 O1 119.3(5) 2_665 . ?
O1 Zr01 O1 76.2(5) 11_565 . ?
O1 Zr01 O1 74.2(5) 12_655 . ?
O1 Zr01 O1 74.2(5) 2_665 11_565 ?
O1 Zr01 O1 76.2(5) 2_665 12_655 ?
O1 Zr01 O1 119.3(5) 12_655 11_565 ?
O3 Zr01 Zr02 35.34(18) . . ?
O3 Zr01 Zr02 35.34(18) . 11_565 ?
O3 Zr01 Zr02 35.34(18) 2_665 3_656 ?
O3 Zr01 Zr02 90.6(3) . 9_666 ?
O3 Zr01 Zr02 90.6(3) 2_665 11_565 ?
O3 Zr01 Zr02 90.6(3) 2_665 . ?
O3 Zr01 Zr02 90.6(3) . 3_656 ?
O3 Zr01 Zr02 35.34(18) 2_665 9_666 ?
O3 Zr01 O1 141.6(3) 2_665 12_655 ?
O3 Zr01 O1 78.4(4) 2_665 . ?
O3 Zr01 O1 78.4(4) . 12_655 ?
O3 Zr01 O1 78.4(4) 2_665 11_565 ?
O3 Zr01 O1 141.6(3) 2_665 2_665 ?
O3 Zr01 O1 141.6(3) . 11_565 ?
O3 Zr01 O1 78.4(4) . 2_665 ?
O3 Zr01 O1 141.6(3) . . ?
O3 Zr01 O3 109.6(7) . 2_665 ?
O4 Zr01 Zr02 90.6(4) 2_665 . ?
O4 Zr01 Zr02 90.6(4) 2_665 3_656 ?
O4 Zr01 Zr02 35.3(2) . . ?
O4 Zr01 Zr02 90.6(4) . 9_666 ?
O4 Zr01 Zr02 90.6(4) . 11_565 ?
O4 Zr01 Zr02 35.3(2) 2_665 9_666 ?
O4 Zr01 Zr02 35.3(2) . 3_656 ?
O4 Zr01 Zr02 35.3(2) 2_665 11_565 ?
O4 Zr01 O1 142.7(3) 2_665 2_665 ?
O4 Zr01 O1 77.7(4) 2_665 . ?
O4 Zr01 O1 142.7(3) 2_665 11_565 ?
O4 Zr01 O1 77.7(4) 2_665 12_655 ?
O4 Zr01 O1 77.7(4) . 11_565 ?
O4 Zr01 O1 142.7(3) . 12_655 ?
O4 Zr01 O1 77.7(4) . 2_665 ?
O4 Zr01 O1 142.7(3) . . ?
O4 Zr01 O3 70.6(3) . 2_665 ?
O4 Zr01 O3 70.6(3) 2_665 . ?
O4 Zr01 O3 70.6(3) 2_665 2_665 ?
O4 Zr01 O3 70.6(3) . . ?
O4 Zr01 O4 109.5(9) . 2_665 ?
Zr01 Zr02 Zr01 88.54(9) . 9_666 ?
Zr01 Zr02 Zr02 59.55(4) 9_666 11_565 ?
Zr01 Zr02 Zr02 59.55(4) . 11_565 ?
Zr01 Zr02 Zr02 59.61(5) . 3_656 ?
Zr01 Zr02 Zr02 59.61(5) 9_666 3_656 ?
Zr02 Zr02 Zr02 90.0 3_656 11_565 ?
O2 Zr02 Zr01 158.7(3) 9_666 . ?
O2 Zr02 Zr01 70.3(3) 2_665 . ?
O2 Zr02 Zr01 158.7(3) 2_665 9_666 ?
O2 Zr02 Zr01 70.3(3) 9_666 9_666 ?
O2 Zr02 Zr02 108.5(3) 2_665 3_656 ?
O2 Zr02 Zr02 105.7(3) 9_666 11_565 ?
O2 Zr02 Zr02 108.5(3) 9_666 3_656 ?
O2 Zr02 Zr02 105.7(3) 2_665 11_565 ?
O2 Zr02 O2 130.7(5) 9_666 2_665 ?
O2 Zr02 O5 71.8(3) 2_665 . ?
O2 Zr02 O5 71.8(3) 9_666 . ?
O3 Zr02 Zr01 88.3(3) . 9_666 ?
O3 Zr02 Zr01 36.4(3) 10_556 9_666 ?
O3 Zr02 Zr01 88.3(3) 10_556 . ?
O3 Zr02 Zr01 36.4(3) . . ?
O3 Zr02 Zr02 90.5(4) . 3_656 ?
O3 Zr02 Zr02 90.5(4) 10_556 3_656 ?
O3 Zr02 Zr02 33.7(3) . 11_565 ?
O3 Zr02 Zr02 33.7(3) 10_556 11_565 ?
O3 Zr02 O2 73.6(4) . 2_665 ?
O3 Zr02 O2 136.6(4) . 9_666 ?
O3 Zr02 O2 136.6(4) 10_556 2_665 ?
O3 Zr02 O2 73.6(4) 10_556 9_666 ?
O3 Zr02 O3 67.4(5) 10_556 . ?
O3 Zr02 O4 108.2(6) 10_556 . ?
O3 Zr02 O4 71.9(5) 10_556 10_556 ?
O3 Zr02 O4 71.9(5) . . ?
O3 Zr02 O4 108.2(6) . 10_556 ?
O3 Zr02 O6 146.2(2) . . ?
O3 Zr02 O6 146.2(2) 10_556 . ?
O3 Zr02 O5 88.7(6) . . ?
O3 Zr02 O5 88.7(6) 10_556 . ?
O4 Zr02 Zr01 35.5(3) . . ?
O4 Zr02 Zr01 35.5(3) 10_556 9_666 ?
O4 Zr02 Zr01 88.3(4) . 9_666 ?
O4 Zr02 Zr01 88.3(4) 10_556 . ?
O4 Zr02 Zr02 34.1(3) . 3_656 ?
O4 Zr02 Zr02 89.6(4) . 11_565 ?
O4 Zr02 Zr02 34.1(3) 10_556 3_656 ?
O4 Zr02 Zr02 89.6(4) 10_556 11_565 ?
O4 Zr02 O2 140.8(4) 10_556 2_665 ?
O4 Zr02 O2 75.8(4) . 2_665 ?
O4 Zr02 O2 140.8(4) . 9_666 ?
O4 Zr02 O2 75.8(4) 10_556 9_666 ?
O4 Zr02 O4 68.3(6) . 10_556 ?
O4 Zr02 O6 87.3(5) 10_556 . ?
O4 Zr02 O6 87.3(5) . . ?
O4 Zr02 O5 145.8(3) 10_556 . ?
O4 Zr02 O5 145.8(3) . . ?
O6 Zr02 Zr01 118.2(3) . . ?
O6 Zr02 Zr01 118.2(3) . 9_666 ?
O6 Zr02 Zr02 86.3(4) . 3_656 ?
O6 Zr02 Zr02 176.3(4) . 11_565 ?
O6 Zr02 O2 75.6(3) . 2_665 ?
O6 Zr02 O2 75.6(3) . 9_666 ?
O6 Zr02 O5 94.7(7) . . ?
O5 Zr02 Zr01 119.8(3) . . ?
O5 Zr02 Zr01 119.8(3) . 9_666 ?
O5 Zr02 Zr02 89.0(5) . 11_565 ?
O5 Zr02 Zr02 179.0(5) . 3_656 ?
C1 O1 Zr01 136.7(10) . . ?
C1 O2 Zr02 138.1(11) . 9_666 ?
Zr02 O3 Zr01 108.2(5) . . ?
Zr02 O3 Zr01 108.2(5) 11_565 . ?
Zr02 O3 Zr02 112.6(5) 11_565 . ?
Zr02 O4 Zr01 109.2(4) . . ?
Zr02 O4 Zr01 109.2(4) 3_656 . ?
Zr02 O4 Zr02 111.7(6) 3_656 . ?
C1 C2 C7 119.7(13) . . ?
C3 C2 C1 123.4(14) . . ?
C3 C2 C7 116.1(12) . . ?
O1 C1 O2 119.2(15) . . ?
O1 C1 C2 119.4(15) . . ?
O2 C1 C2 120.9(15) . . ?
C5 C6 H6 118.4 . . ?
C7 C6 H6 118.4 . . ?
C7 C6 C5 123.2(14) . . ?
C2 C3 H3 118.4 . . ?
C2 C3 C4 123.2(13) . . ?
C4 C3 H3 118.4 . . ?
C9 N1 C8 106.5(13) . . ?
C6 C5 C8 119.0(13) . . ?
C4 C5 C6 118.7(13) . . ?
C4 C5 C8 122.0(14) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 C3 118.0(13) . . ?
C5 C4 H4 121.0 . . ?
C2 C7 H7 120.4 . . ?
C6 C7 C2 119.2(13) . . ?
C6 C7 H7 120.4 . . ?
N1 C8 C5 119.6(12) . . ?
N1 C8 C8 108.4(8) . 6 ?
C8 C8 C5 132.0(8) 6 . ?
C11 C10 C9 119.5(11) . . ?
C11 C10 C9 119.5(11) 6 . ?
C11 C10 C11 121(2) . 6 ?
N1 C9 N1 110.1(18) . 6 ?
N1 C9 C10 125.0(9) . . ?
N1 C9 C10 125.0(9) 6 . ?
C10 C11 C12 119.9(15) . . ?
C11 C11 C10 119.5(11) 10 . ?
C11 C11 C12 120.3(13) 10 . ?
C13 C13 H13 120.7 10 . ?
C12 C13 C13 118.6(13) . 10 ?
C12 C13 H13 120.7 . . ?
C11 C12 C13 121(3) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?

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
Zr01 O1 C1 O2 9(3) . . . . ?
Zr01 O1 C1 C2 -163.3(11) . . . . ?
Zr02 O2 C1 O1 -15(3) 9_666 . . . ?
Zr02 O2 C1 C2 157.0(13) 9_666 . . . ?
C2 C3 C4 C5 -10(3) . . . . ?
C1 C2 C3 C4 -178.2(16) . . . . ?
C1 C2 C7 C6 177.7(16) . . . . ?
C6 C5 C4 C3 7(2) . . . . ?
C6 C5 C8 N1 -38(3) . . . . ?
C6 C5 C8 C8 141(3) . . . 6 ?
C3 C2 C1 O1 -162.5(17) . . . . ?
C3 C2 C1 O2 25(3) . . . . ?
C3 C2 C7 C6 -12(2) . . . . ?
C5 C6 C7 C2 10(3) . . . . ?
C4 C5 C8 N1 148.7(17) . . . . ?
C4 C5 C8 C8 -33(4) . . . 6 ?
C7 C2 C1 O1 7(3) . . . . ?
C7 C2 C1 O2 -165.5(16) . . . . ?
C7 C2 C3 C4 12(3) . . . . ?
C7 C6 C5 C4 -8(3) . . . . ?
C7 C6 C5 C8 178.3(16) . . . . ?
C8 N1 C9 N1 -1.0(10) . . . 6 ?
C8 N1 C9 C10 179.0(10) . . . . ?
C8 C5 C4 C3 -179.6(16) . . . . ?
C10 C11 C12 C13 180(2) . . . . ?
C9 N1 C8 C5 -178.7(14) . . . . ?
C9 N1 C8 C8 3(3) . . . 6 ?
C9 C10 C11 C11 180.000(5) . . . 10 ?
C9 C10 C11 C12 -7(3) . . . . ?
C11 C10 C9 N1 121.6(15) . . . . ?
C11 C10 C9 N1 -58.4(15) 6 . . . ?
C11 C10 C9 N1 -58.4(15) . . . 6 ?
C11 C10 C9 N1 121.6(15) 6 . . 6 ?
C11 C10 C11 C11 -0.003(5) 6 . . 10 ?
C11 C10 C11 C12 173(3) 6 . . . ?
C11 C11 C12 C13 -7(4) 10 . . . ?
C13 C13 C12 C11 7(4) 10 . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.230 -0.053 -0.189 5995.6 1866.4 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 2235398'
loop_
_audit_author_name
_audit_author_address
'Bao Li'
;Huazhong university of science and technology
China
;
_audit_update_record             
;
2023-01-10 deposited with the CCDC.	2023-07-25 downloaded from the CCDC.
;
_audit_creation_date             2022-12-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C48 H24 N4 O20 Zr3'
_chemical_formula_sum            'C48 H24 N4 O20 Zr3'
_chemical_formula_weight         1250.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zr Zr -2.9673 0.5597 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           65
_space_group_name_H-M_alt        'C m m m'
_space_group_name_Hall           '-C 2 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x, y, -z'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z'
'x, -y, z'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'

_cell_length_a                   14.118(7)
_cell_length_b                   26.830(12)
_cell_length_c                   24.693(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     9354(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    611
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      15.36
_cell_measurement_theta_min      2.81
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.372
_exptl_absorpt_correction_T_max  0.7440
_exptl_absorpt_correction_T_min  0.3440
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1333 before and 0.1028 after correction.
The Ratio of minimum to maximum transmission is 0.4624.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    0.888
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2480.0
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1764
_diffrn_reflns_av_unetI/netI     0.0839
_diffrn_reflns_Laue_measured_fraction_full 0.951
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17822
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        16.518
_diffrn_reflns_theta_max         16.518
_diffrn_reflns_theta_min         1.630
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                943
_reflns_number_total             1365
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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)'
_refine_diff_density_max         1.401
_refine_diff_density_min         -1.203
_refine_diff_density_rms         0.172
_refine_ls_extinction_coef       0.0011(4)
_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   1.372
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         1365
_refine_ls_number_restraints     184
_refine_ls_R_factor_all          0.1571
_refine_ls_R_factor_gt           0.1348
_refine_ls_restrained_S_all      1.454
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3249
_refine_ls_wR_factor_ref         0.3450
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C6-C5
 1.45 with sigma of 0.02
 C1-C2
 1.45 with sigma of 0.02
 C1-O2
 1.25 with sigma of 0.02
 C7-C2
 1.45 with sigma of 0.02
 C5-C7
 2.45 with sigma of 0.02
 C1-C7
 2.45 with sigma of 0.02
 C7-C5
 2.45 with sigma of 0.02
 C3-C5
 2.45 with sigma of 0.02
 C6-C4
 2.45 with sigma of 0.02
 C5-C8
 1.45 with sigma of 0.02
 C8-C8_$1
 1.45 with sigma of 0.02
 C9-C10
 1.45 with sigma of 0.02
 C8-N1
 1.45 with sigma of 0.02
 C11-C11_$2
 1.5 with sigma of 0.02
 C2-C6
 2.45 with sigma of 0.02
 C8-N1_$1
 2.4 with sigma of 0.02
 C8-C9
 2.4 with sigma of 0.02
 C10-C11
 1.5 with sigma of 0.02
 C11-C13
 2.5 with sigma of 0.02
 C13-C13_$4
 1.5 with sigma of 0.02
 C14-C13
 1.5 with sigma of 0.02
 C12-C13
 1.5 with sigma of 0.02
 C13-C12_$2
 2.5 with sigma of 0.02
 C12_$3-C14
 2.5 with sigma of 0.02
 C14_$4-C14
 1.45 with sigma of 0.02
 C13_$4-C14
 2.1 with sigma of 0.02
 C12-C12_$3
 2.2 with sigma of 0.02
2. Restrained planarity
 C3, C2, C1, C7
 with sigma of 0.1
 C6, C5, C8, C4
 with sigma of 0.1
 C14, C13, C13_$4, C14_$4
 with sigma of 0.1
3. Rigid bond restraints
 Zr02, O3, Zr01, O5, O6
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C1 \\sim O1 \\sim O2 \\sim C2: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
Zr02 \\sim O1 \\sim O3 \\sim O4 \\sim Zr01 \\sim O5 \\sim O6: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C11 \\sim C10: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 2A
C12 \\sim C14 \\sim C13: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
Uanis(O5) \\sim Ueq, Uanis(O6) \\sim Ueq, Uanis(Zr01) \\sim Ueq, Uanis(C1)
\\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(C2) \\sim Ueq,
Uanis(C7) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C5) \\sim
Ueq, Uanis(C4) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C10)
\\sim Ueq, Uanis(C13) \\sim Ueq: with sigma of 0.025 and sigma for terminal
atoms of 0.04
Uanis(N1) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O1) \\sim Ueq, Uanis(O6) \\sim Ueq, Uanis(O5) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(O6) \\sim Ueq, Uanis(O5) \\sim Ueq: with sigma of 0.0075 and sigma for
terminal atoms of 0.01
Uanis(C1) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.01
Uanis(O3) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.15
5. Others
 Fixed Sof: H14A(0.5) H14B(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C6(H6), C4(H4), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Zr01 Zr 0.6250(3) 0.56629(11) 0.500000 0.0866(19) Uani 1 2 d S TU P . .
Zr02 Zr 0.500000 0.500000 0.40111(13) 0.080(2) Uani 1 4 d S TU P . .
O5 O 0.7733(15) 0.5631(7) 0.500000 0.095(5) Uani 1 2 d S TU P . .
O1 O 0.4046(10) 0.4487(5) 0.3555(5) 0.069(5) Uani 1 1 d . U . . .
O6 O 0.6126(12) 0.6464(7) 0.500000 0.074(5) Uani 1 2 d S TU P . .
C10 C 0.250000 0.250000 0.0559(11) 0.099(12) Uani 1 2 d DS TU P . .
O2 O 0.3275(11) 0.4070(5) 0.4164(6) 0.091(5) Uani 1 1 d D U . . .
O3 O 0.6306(16) 0.500000 0.4520(7) 0.095(6) Uani 1 2 d S TU P . .
O4 O 0.500000 0.5656(7) 0.4527(9) 0.097(7) Uani 1 2 d S T P . .
C8 C 0.2641(15) 0.2758(4) 0.2049(7) 0.085(7) Uani 1 1 d D U . . .
C3 C 0.2568(15) 0.3446(8) 0.3362(8) 0.082(7) Uani 1 1 d D U . . .
H3 H 0.225328 0.343370 0.369209 0.099 Uiso 1 1 calc R U . . .
C2 C 0.3230(15) 0.3796(8) 0.3275(8) 0.101(8) Uani 1 1 d D U . . .
C1 C 0.3545(17) 0.4159(9) 0.3681(8) 0.073(7) Uani 1 1 d D U . . .
C9 C 0.250000 0.250000 0.1141(9) 0.110(12) Uani 1 2 d DS TU P . .
C7 C 0.3687(14) 0.3841(7) 0.2755(8) 0.087(8) Uani 1 1 d D U . . .
H7 H 0.407970 0.411105 0.268312 0.104 Uiso 1 1 calc R U . . .
C6 C 0.3534(14) 0.3472(8) 0.2355(7) 0.081(7) Uani 1 1 d D U . . .
H6 H 0.388436 0.346700 0.203658 0.097 Uiso 1 1 calc R U . . .
C4 C 0.2355(14) 0.3106(8) 0.2965(9) 0.087(7) Uani 1 1 d D U . . .
H4 H 0.188986 0.286825 0.303134 0.104 Uiso 1 1 calc R U . . .
C5 C 0.2821(14) 0.3106(6) 0.2460(7) 0.075(7) Uani 1 1 d D U . . .
C11 C 0.1634(16) 0.2313(13) 0.0303(4) 0.149(11) Uani 1 1 d D U . . .
N1 N 0.2738(11) 0.2915(5) 0.1489(6) 0.073(5) Uani 1 1 d D U . . .
C13 C 0.000000 0.1977(15) 0.0300(4) 0.25(2) Uani 1 2 d DS TU P . .
C14 C 0.000000 0.1417(14) 0.0295(4) 0.35(3) Uani 1 2 d DS TU P . .
H14A H 0.056563 0.127125 0.045150 0.420 Uiso 0.5 1 calc R U P . .
H14B H -0.056563 0.127125 0.045150 0.420 Uiso 0.5 1 calc R U P . .
O7 O 0.302(6) 0.216(2) 0.0333(18) 0.48(5) Uani 1 1 d . . . . .
C12 C 0.0783(7) 0.2217(13) 0.0573(9) 0.225(18) Uani 1 1 d D U . . .
H12 H 0.071989 0.230800 0.093501 0.269 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
Zr01 Zr01 3.557(6) 11_565 ?
Zr01 Zr01 3.528(8) 3_656 ?
Zr01 Zr02 3.498(3) . ?
Zr01 Zr02 3.499(3) 9_666 ?
Zr01 O5 2.10(2) . ?
Zr01 O6 2.157(18) . ?
Zr01 O2 2.287(14) 9_666 ?
Zr01 O2 2.287(14) 2_665 ?
Zr01 O3 2.139(10) . ?
Zr01 O3 2.139(10) 10_556 ?
Zr01 O4 2.116(13) 10_556 ?
Zr01 O4 2.116(13) . ?
Zr02 O1 2.231(14) 2_665 ?
Zr02 O1 2.231(14) . ?
Zr02 O1 2.231(14) 12_655 ?
Zr02 O1 2.231(14) 11_565 ?
Zr02 O3 2.23(2) 2_665 ?
Zr02 O3 2.23(2) . ?
Zr02 O4 2.172(18) 2_665 ?
Zr02 O4 2.172(18) . ?
O1 C1 1.17(2) . ?
C10 C9 1.438(19) . ?
C10 C11 1.465(16) 6 ?
C10 C11 1.465(16) . ?
C10 O7 1.29(6) 6 ?
C10 O7 1.29(6) . ?
O2 C1 1.275(15) . ?
C8 C8 1.439(18) 6 ?
C8 C5 1.403(14) . ?
C8 N1 1.454(14) . ?
C3 H3 0.9300 . ?
C3 C2 1.34(2) . ?
C3 C4 1.37(2) . ?
C2 C1 1.466(18) . ?
C2 C7 1.440(17) . ?
C9 N1 1.447(18) 6 ?
C9 N1 1.447(18) . ?
C7 H7 0.9300 . ?
C7 C6 1.415(19) . ?
C6 H6 0.9300 . ?
C6 C5 1.429(16) . ?
C4 H4 0.9300 . ?
C4 C5 1.41(2) . ?
C11 C11 1.49(2) 10 ?
C11 O7 1.49(5) 6 ?
C11 C12 1.40(2) . ?
C13 C13 1.484(19) 3 ?
C13 C14 1.503(17) . ?
C13 C12 1.445(13) . ?
C13 C12 1.445(13) 12 ?
C14 C14 1.45(2) 3 ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
O7 O7 1.64(9) 10 ?
C12 H12 0.9300 . ?

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
Zr01 Zr01 Zr01 90.0 3_656 11_565 ?
Zr02 Zr01 Zr01 59.72(6) . 3_656 ?
Zr02 Zr01 Zr01 59.44(5) 9_666 11_565 ?
Zr02 Zr01 Zr01 59.72(6) 9_666 3_656 ?
Zr02 Zr01 Zr01 59.44(5) . 11_565 ?
Zr02 Zr01 Zr02 88.54(11) . 9_666 ?
O5 Zr01 Zr01 87.7(5) . 11_565 ?
O5 Zr01 Zr01 177.7(5) . 3_656 ?
O5 Zr01 Zr02 118.9(3) . . ?
O5 Zr01 Zr02 118.9(3) . 9_666 ?
O5 Zr01 O6 96.9(7) . . ?
O5 Zr01 O2 73.7(5) . 2_665 ?
O5 Zr01 O2 73.7(5) . 9_666 ?
O5 Zr01 O3 85.9(7) . 10_556 ?
O5 Zr01 O3 85.9(7) . . ?
O5 Zr01 O4 146.4(5) . . ?
O5 Zr01 O4 146.4(5) . 10_556 ?
O6 Zr01 Zr01 175.4(5) . 11_565 ?
O6 Zr01 Zr01 85.4(5) . 3_656 ?
O6 Zr01 Zr02 117.8(3) . . ?
O6 Zr01 Zr02 117.8(3) . 9_666 ?
O6 Zr01 O2 73.2(4) . 9_666 ?
O6 Zr01 O2 73.2(4) . 2_665 ?
O2 Zr01 Zr01 108.3(4) 2_665 11_565 ?
O2 Zr01 Zr01 108.3(4) 9_666 11_565 ?
O2 Zr01 Zr01 107.1(4) 9_666 3_656 ?
O2 Zr01 Zr01 107.1(4) 2_665 3_656 ?
O2 Zr01 Zr02 159.7(4) 9_666 . ?
O2 Zr01 Zr02 159.7(4) 2_665 9_666 ?
O2 Zr01 Zr02 71.2(4) 9_666 9_666 ?
O2 Zr01 Zr02 71.2(4) 2_665 . ?
O2 Zr01 O2 129.1(8) 9_666 2_665 ?
O3 Zr01 Zr01 33.8(4) . 11_565 ?
O3 Zr01 Zr01 92.1(6) . 3_656 ?
O3 Zr01 Zr01 33.8(4) 10_556 11_565 ?
O3 Zr01 Zr01 92.1(6) 10_556 3_656 ?
O3 Zr01 Zr02 37.7(5) 10_556 9_666 ?
O3 Zr01 Zr02 89.0(5) 10_556 . ?
O3 Zr01 Zr02 89.0(5) . 9_666 ?
O3 Zr01 Zr02 37.7(5) . . ?
O3 Zr01 O6 146.3(4) . . ?
O3 Zr01 O6 146.3(4) 10_556 . ?
O3 Zr01 O2 138.7(6) . 9_666 ?
O3 Zr01 O2 138.6(6) 10_556 2_665 ?
O3 Zr01 O2 75.5(5) . 2_665 ?
O3 Zr01 O2 75.5(5) 10_556 9_666 ?
O3 Zr01 O3 67.3(8) 10_556 . ?
O4 Zr01 Zr01 33.5(5) . 3_656 ?
O4 Zr01 Zr01 89.5(5) . 11_565 ?
O4 Zr01 Zr01 33.5(5) 10_556 3_656 ?
O4 Zr01 Zr01 89.5(5) 10_556 11_565 ?
O4 Zr01 Zr02 87.7(6) . 9_666 ?
O4 Zr01 Zr02 87.7(6) 10_556 . ?
O4 Zr01 Zr02 35.9(5) . . ?
O4 Zr01 Zr02 35.9(5) 10_556 9_666 ?
O4 Zr01 O6 86.7(7) 10_556 . ?
O4 Zr01 O6 86.7(7) . . ?
O4 Zr01 O2 138.2(6) . 9_666 ?
O4 Zr01 O2 75.5(7) . 2_665 ?
O4 Zr01 O2 138.2(6) 10_556 2_665 ?
O4 Zr01 O2 75.5(7) 10_556 9_666 ?
O4 Zr01 O3 73.6(7) 10_556 10_556 ?
O4 Zr01 O3 109.2(8) 10_556 . ?
O4 Zr01 O3 73.6(7) . . ?
O4 Zr01 O3 109.2(8) . 10_556 ?
O4 Zr01 O4 67.0(10) 10_556 . ?
Zr01 Zr02 Zr01 60.57(12) 11_565 9_666 ?
Zr01 Zr02 Zr01 60.57(12) . 3_656 ?
Zr01 Zr02 Zr01 91.46(11) 11_565 3_656 ?
Zr01 Zr02 Zr01 61.12(11) . 11_565 ?
Zr01 Zr02 Zr01 61.12(11) 3_656 9_666 ?
Zr01 Zr02 Zr01 91.46(11) . 9_666 ?
O1 Zr02 Zr01 74.6(4) 12_655 11_565 ?
O1 Zr02 Zr01 110.1(4) . 11_565 ?
O1 Zr02 Zr01 111.2(4) 12_655 . ?
O1 Zr02 Zr01 110.1(4) 2_665 3_656 ?
O1 Zr02 Zr01 111.2(4) 2_665 11_565 ?
O1 Zr02 Zr01 74.6(4) 11_565 3_656 ?
O1 Zr02 Zr01 166.1(4) 11_565 11_565 ?
O1 Zr02 Zr01 166.1(4) 12_655 3_656 ?
O1 Zr02 Zr01 74.6(4) . 9_666 ?
O1 Zr02 Zr01 111.2(4) 11_565 9_666 ?
O1 Zr02 Zr01 111.2(4) . 3_656 ?
O1 Zr02 Zr01 110.1(4) 11_565 . ?
O1 Zr02 Zr01 166.1(4) . . ?
O1 Zr02 Zr01 166.1(4) 2_665 9_666 ?
O1 Zr02 Zr01 110.1(4) 12_655 9_666 ?
O1 Zr02 Zr01 74.6(4) 2_665 . ?
O1 Zr02 O1 76.2(7) 2_665 12_655 ?
O1 Zr02 O1 74.3(7) 12_655 . ?
O1 Zr02 O1 76.2(7) 11_565 . ?
O1 Zr02 O1 119.3(8) 2_665 . ?
O1 Zr02 O1 74.3(7) 2_665 11_565 ?
O1 Zr02 O1 119.3(8) 12_655 11_565 ?
O1 Zr02 O3 141.6(3) . . ?
O1 Zr02 O3 77.6(5) 11_565 2_665 ?
O1 Zr02 O3 77.6(5) 2_665 . ?
O1 Zr02 O3 77.6(5) 12_655 . ?
O1 Zr02 O3 141.6(3) 2_665 2_665 ?
O1 Zr02 O3 141.6(3) 12_655 2_665 ?
O1 Zr02 O3 77.6(5) . 2_665 ?
O1 Zr02 O3 141.6(3) 11_565 . ?
O3 Zr02 Zr01 35.9(3) 2_665 3_656 ?
O3 Zr02 Zr01 91.4(5) . 9_666 ?
O3 Zr02 Zr01 91.4(5) 2_665 11_565 ?
O3 Zr02 Zr01 35.9(3) . 11_565 ?
O3 Zr02 Zr01 91.4(5) . 3_656 ?
O3 Zr02 Zr01 35.9(3) 2_665 9_666 ?
O3 Zr02 Zr01 91.4(5) 2_665 . ?
O3 Zr02 Zr01 35.9(3) . . ?
O3 Zr02 O3 111.5(10) . 2_665 ?
O4 Zr02 Zr01 90.1(6) . 9_666 ?
O4 Zr02 Zr01 34.8(3) 2_665 9_666 ?
O4 Zr02 Zr01 34.8(3) . 3_656 ?
O4 Zr02 Zr01 90.1(6) . 11_565 ?
O4 Zr02 Zr01 90.1(6) 2_665 . ?
O4 Zr02 Zr01 34.8(3) . . ?
O4 Zr02 Zr01 34.8(3) 2_665 11_565 ?
O4 Zr02 Zr01 90.1(6) 2_665 3_656 ?
O4 Zr02 O1 142.7(3) 2_665 11_565 ?
O4 Zr02 O1 78.3(6) 2_665 12_655 ?
O4 Zr02 O1 142.7(3) . 12_655 ?
O4 Zr02 O1 78.3(6) . 2_665 ?
O4 Zr02 O1 142.7(3) . . ?
O4 Zr02 O1 78.3(6) . 11_565 ?
O4 Zr02 O1 142.7(3) 2_665 2_665 ?
O4 Zr02 O1 78.3(6) 2_665 . ?
O4 Zr02 O3 70.7(4) 2_665 2_665 ?
O4 Zr02 O3 70.7(4) 2_665 . ?
O4 Zr02 O3 70.7(4) . . ?
O4 Zr02 O3 70.7(4) . 2_665 ?
O4 Zr02 O4 108.2(13) 2_665 . ?
C1 O1 Zr02 133.9(13) . . ?
C9 C10 C11 115.6(12) . . ?
C9 C10 C11 115.6(12) . 6 ?
C11 C10 C11 129(2) . 6 ?
O7 C10 C9 116(3) 6 . ?
O7 C10 C9 116(3) . . ?
O7 C10 C11 65(3) . 6 ?
O7 C10 C11 93(3) 6 6 ?
O7 C10 C11 65(3) 6 . ?
O7 C10 C11 93(3) . . ?
O7 C10 O7 129(5) 6 . ?
C1 O2 Zr01 134.3(14) . 9_666 ?
Zr01 O3 Zr01 112.5(8) . 11_565 ?
Zr01 O3 Zr02 106.3(7) . . ?
Zr01 O3 Zr02 106.3(7) 11_565 . ?
Zr01 O4 Zr01 113.0(10) . 3_656 ?
Zr01 O4 Zr02 109.3(6) . . ?
Zr01 O4 Zr02 109.3(6) 3_656 . ?
C8 C8 N1 107.8(7) 6 . ?
C5 C8 C8 133.7(9) . 6 ?
C5 C8 N1 118.5(12) . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.3(18) . . ?
C4 C3 H3 119.9 . . ?
C3 C2 C1 124.5(18) . . ?
C3 C2 C7 120.8(17) . . ?
C7 C2 C1 114.7(18) . . ?
O1 C1 O2 124.8(19) . . ?
O1 C1 C2 120.0(17) . . ?
O2 C1 C2 115.1(18) . . ?
C10 C9 N1 126.4(7) . 6 ?
C10 C9 N1 126.4(7) . . ?
N1 C9 N1 107.1(15) . 6 ?
C2 C7 H7 120.2 . . ?
C6 C7 C2 119.7(14) . . ?
C6 C7 H7 120.2 . . ?
C7 C6 H6 121.3 . . ?
C7 C6 C5 117.5(13) . . ?
C5 C6 H6 121.3 . . ?
C3 C4 H4 119.0 . . ?
C3 C4 C5 121.9(17) . . ?
C5 C4 H4 119.0 . . ?
C8 C5 C6 117.0(17) . . ?
C8 C5 C4 123.7(18) . . ?
C4 C5 C6 119.3(13) . . ?
C10 C11 C11 115.6(12) . 10 ?
C10 C11 O7 52(3) . 6 ?
O7 C11 C11 92.9(18) 6 10 ?
C12 C11 C10 125.0(16) . . ?
C12 C11 C11 118.6(9) . 10 ?
C12 C11 O7 115(4) . 6 ?
C9 N1 C8 108.6(11) . . ?
C13 C13 C14 89.4(6) 3 . ?
C12 C13 C13 117.8(11) . 3 ?
C12 C13 C13 117.8(11) 12 3 ?
C12 C13 C14 116.7(13) . . ?
C12 C13 C14 116.7(13) 12 . ?
C12 C13 C12 99.8(15) . 12 ?
C13 C14 H14A 113.5 . . ?
C13 C14 H14B 113.5 . . ?
C14 C14 C13 90.6(6) 3 . ?
C14 C14 H14A 113.5 3 . ?
C14 C14 H14B 113.5 3 . ?
H14A C14 H14B 110.8 . . ?
C10 O7 C11 63(2) . 6 ?
C10 O7 O7 116(3) . 10 ?
C11 O7 O7 87.1(18) 6 10 ?
C11 C12 C13 121.1(17) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?

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
Zr01 O2 C1 O1 -14(4) 9_666 . . . ?
Zr01 O2 C1 C2 162.6(12) 9_666 . . . ?
Zr02 O1 C1 O2 15(4) . . . . ?
Zr02 O1 C1 C2 -161.3(12) . . . . ?
C10 C9 N1 C8 179.6(10) . . . . ?
C10 C11 C12 C13 -173(2) . . . . ?
C8 C8 C5 C6 147(3) 6 . . . ?
C8 C8 C5 C4 -32(4) 6 . . . ?
C8 C8 N1 C9 1(3) 6 . . . ?
C3 C2 C1 O1 -171(2) . . . . ?
C3 C2 C1 O2 12(3) . . . . ?
C3 C2 C7 C6 -9(3) . . . . ?
C3 C4 C5 C8 178.3(19) . . . . ?
C3 C4 C5 C6 0(2) . . . . ?
C2 C3 C4 C5 1(3) . . . . ?
C2 C7 C6 C5 9(3) . . . . ?
C1 C2 C7 C6 171.6(19) . . . . ?
C9 C10 C11 C11 180.000(4) . . . 10 ?
C9 C10 C11 O7 108(3) . . . 6 ?
C9 C10 C11 C12 11(4) . . . . ?
C9 C10 O7 C11 -107.7(15) . . . 6 ?
C9 C10 O7 O7 180.003(9) . . . 10 ?
C7 C2 C1 O1 8(3) . . . . ?
C7 C2 C1 O2 -168(2) . . . . ?
C7 C6 C5 C8 176.8(18) . . . . ?
C7 C6 C5 C4 -5(2) . . . . ?
C4 C3 C2 C1 -177(2) . . . . ?
C4 C3 C2 C7 4(3) . . . . ?
C5 C8 N1 C9 -178.8(14) . . . . ?
C11 C10 C9 N1 50.9(18) . . . 6 ?
C11 C10 C9 N1 -129.1(18) . . . . ?
C11 C10 C9 N1 -129.1(18) 6 . . 6 ?
C11 C10 C9 N1 50.9(18) 6 . . . ?
C11 C10 C11 C11 0.001(3) 6 . . 10 ?
C11 C10 C11 O7 -72(3) 6 . . 6 ?
C11 C10 C11 C12 -169(4) 6 . . . ?
C11 C10 O7 C11 132(2) . . . 6 ?
C11 C10 O7 O7 59.7(17) . . . 10 ?
C11 C10 O7 O7 -72.3(15) 6 . . 10 ?
C11 C11 C12 C13 19(3) 10 . . . ?
N1 C8 C5 C6 -33(2) . . . . ?
N1 C8 C5 C4 148.2(18) . . . . ?
N1 C9 N1 C8 -0.4(10) 6 . . . ?
C13 C13 C14 C14 0.000(1) 3 . . 3 ?
C13 C13 C12 C11 -18(3) 3 . . . ?
C14 C13 C12 C11 86(3) . . . . ?
O7 C10 C9 N1 124(4) . . . . ?
O7 C10 C9 N1 -56(4) 6 . . . ?
O7 C10 C9 N1 -56(4) . . . 6 ?
O7 C10 C9 N1 124(4) 6 . . 6 ?
O7 C10 C11 C11 -60(2) . . . 10 ?
O7 C10 C11 C11 72(3) 6 . . 10 ?
O7 C10 C11 O7 -132(5) . . . 6 ?
O7 C10 C11 C12 131(5) . . . . ?
O7 C10 C11 C12 -97(5) 6 . . . ?
O7 C10 O7 C11 72.3(15) 6 . . 6 ?
O7 C10 O7 O7 0.006(13) 6 . . 10 ?
O7 C11 C12 C13 127(3) 6 . . . ?
C12 C13 C14 C14 -121.1(12) . . . 3 ?
C12 C13 C14 C14 121.1(12) 12 . . 3 ?
C12 C13 C12 C11 -147(2) 12 . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.230 -0.053 -0.189 5995.6 1866.4 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
