# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_YSH-Jiang-Zr
_audit_block_doi                 10.5517/ccdc.csd.cc296bd8
_database_code_depnum_ccdc_archive 'CCDC 2121249'
loop_
_audit_author_name
_audit_author_address
'Jihyun Choi'
;ChungAng University
South Korea
;
_audit_update_record             
;
2021-11-10 deposited with the CCDC.	2022-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H42 N4 O2 Zr'
_chemical_formula_weight         413.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zr Zr -0.1862 2.2449 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8032(2)
_cell_length_b                   9.05680(10)
_cell_length_c                   15.4925(2)
_cell_angle_alpha                75.6210(10)
_cell_angle_beta                 86.3200(10)
_cell_angle_gamma                65.266(2)
_cell_volume                     1085.63(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    10944
_cell_measurement_theta_min      5.5340
_cell_measurement_theta_max      79.0560

_exptl_crystal_description       cube
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_F_000             444
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.235
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.108
_exptl_absorpt_coefficient_mu    4.249
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.57654
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'SCALE3 ABSPACK'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'

_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14033
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         5.539
_diffrn_reflns_theta_max         79.130
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4560
_reflns_number_gt                4357
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+0.3306P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4560
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0786
_refine_ls_wR_factor_gt          0.0783
_refine_ls_goodness_of_fit_ref   1.701
_refine_ls_restrained_S_all      1.701
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.33059(2) 0.37449(2) 0.73267(2) 0.01412(7) Uani 1 1 d . . . . .
O2 O 0.2001(2) 0.2389(2) 0.79134(11) 0.0210(4) Uani 1 1 d . . . . .
O10 O 0.5713(2) 0.2038(2) 0.76339(11) 0.0216(4) Uani 1 1 d . . . . .
N19 N 0.1227(2) 0.5447(3) 0.64499(13) 0.0166(4) Uani 1 1 d . . . . .
N22 N 0.4102(2) 0.5712(3) 0.71535(14) 0.0188(4) Uani 1 1 d . . . . .
N5 N 0.2920(3) 0.3928(3) 0.88593(14) 0.0212(4) Uani 1 1 d . . . . .
N13 N 0.4149(3) 0.2117(3) 0.62185(13) 0.0182(4) Uani 1 1 d . . . . .
C18 C -0.0420(3) 0.5418(4) 0.64988(17) 0.0233(5) Uani 1 1 d . . . . .
H18A H -0.064263 0.512586 0.598059 0.035 Uiso 1 1 calc R U . . .
H18B H -0.125694 0.650499 0.652333 0.035 Uiso 1 1 calc R U . . .
H18C H -0.044586 0.460312 0.702467 0.035 Uiso 1 1 calc R U . . .
C20 C 0.1253(3) 0.6650(3) 0.56366(17) 0.0226(5) Uani 1 1 d . . . . .
H20A H 0.232637 0.669477 0.559908 0.034 Uiso 1 1 calc R U . . .
H20B H 0.039646 0.773796 0.564310 0.034 Uiso 1 1 calc R U . . .
H20C H 0.105307 0.631276 0.513024 0.034 Uiso 1 1 calc R U . . .
C11 C 0.6681(3) 0.0665(3) 0.72772(17) 0.0245(6) Uani 1 1 d . . . . .
C21 C 0.3017(3) 0.7465(3) 0.70737(19) 0.0261(6) Uani 1 1 d . . . . .
H21A H 0.186986 0.763094 0.703649 0.039 Uiso 1 1 calc R U . . .
H21B H 0.326024 0.813230 0.654512 0.039 Uiso 1 1 calc R U . . .
H21C H 0.320060 0.779492 0.758668 0.039 Uiso 1 1 calc R U . . .
C14 C 0.4757(3) 0.3008(3) 0.54434(17) 0.0232(5) Uani 1 1 d . . . . .
H14A H 0.382231 0.394763 0.510717 0.035 Uiso 1 1 calc R U . . .
H14B H 0.534661 0.225885 0.507189 0.035 Uiso 1 1 calc R U . . .
H14C H 0.549737 0.339625 0.564687 0.035 Uiso 1 1 calc R U . . .
C17 C 0.2760(3) 0.1832(4) 0.59132(18) 0.0250(6) Uani 1 1 d . . . . .
H17A H 0.228737 0.134723 0.641963 0.038 Uiso 1 1 calc R U . . .
H17B H 0.317629 0.108299 0.552542 0.038 Uiso 1 1 calc R U . . .
H17C H 0.191447 0.288132 0.559611 0.038 Uiso 1 1 calc R U . . .
C3 C 0.1722(3) 0.1864(3) 0.88174(16) 0.0224(5) Uani 1 1 d . . . . .
C12 C 0.5495(3) 0.0475(3) 0.66649(17) 0.0224(5) Uani 1 1 d . . . . .
H12A H 0.613870 -0.007301 0.621446 0.027 Uiso 1 1 calc R U . . .
H12B H 0.498948 -0.023401 0.701599 0.027 Uiso 1 1 calc R U . . .
C6 C 0.1390(4) 0.5447(4) 0.8882(2) 0.0315(7) Uani 1 1 d . . . . .
H6A H 0.159038 0.642338 0.862005 0.047 Uiso 1 1 calc R U . . .
H6B H 0.108880 0.544008 0.948897 0.047 Uiso 1 1 calc R U . . .
H6C H 0.049401 0.546457 0.855114 0.047 Uiso 1 1 calc R U . . .
C4 C 0.2747(3) 0.2385(4) 0.93546(17) 0.0247(6) Uani 1 1 d . . . . .
H4A H 0.220665 0.256778 0.990795 0.030 Uiso 1 1 calc R U . . .
H4B H 0.385284 0.147858 0.950439 0.030 Uiso 1 1 calc R U . . .
C15 C 0.8174(4) 0.0921(5) 0.6804(2) 0.0373(7) Uani 1 1 d . . . . .
H15A H 0.777086 0.195495 0.635124 0.056 Uiso 1 1 calc R U . . .
H15B H 0.879120 0.000717 0.653374 0.056 Uiso 1 1 calc R U . . .
H15C H 0.889124 0.096144 0.723012 0.056 Uiso 1 1 calc R U . . .
C23 C 0.5826(3) 0.5493(4) 0.72198(19) 0.0283(6) Uani 1 1 d . . . . .
H23A H 0.596927 0.589493 0.771307 0.042 Uiso 1 1 calc R U . . .
H23B H 0.608789 0.611306 0.667846 0.042 Uiso 1 1 calc R U . . .
H23C H 0.656052 0.432497 0.731170 0.042 Uiso 1 1 calc R U . . .
C9 C 0.4339(4) 0.4027(5) 0.92576(19) 0.0377(7) Uani 1 1 d . . . . .
H9A H 0.536247 0.312545 0.916869 0.057 Uiso 1 1 calc R U . . .
H9B H 0.419499 0.393993 0.988497 0.057 Uiso 1 1 calc R U . . .
H9C H 0.438424 0.507903 0.897875 0.057 Uiso 1 1 calc R U . . .
C7 C -0.0165(4) 0.2593(4) 0.89781(19) 0.0315(6) Uani 1 1 d . . . . .
H7A H -0.061489 0.379514 0.881023 0.047 Uiso 1 1 calc R U . . .
H7B H -0.033661 0.222472 0.959818 0.047 Uiso 1 1 calc R U . . .
H7C H -0.071969 0.221400 0.862598 0.047 Uiso 1 1 calc R U . . .
C16 C 0.7368(4) -0.0933(4) 0.8036(2) 0.0388(8) Uani 1 1 d . . . . .
H16A H 0.811627 -0.084378 0.842485 0.058 Uiso 1 1 calc R U . . .
H16B H 0.796134 -0.188515 0.779091 0.058 Uiso 1 1 calc R U . . .
H16C H 0.645709 -0.106927 0.836844 0.058 Uiso 1 1 calc R U . . .
C8 C 0.2383(4) -0.0052(4) 0.9088(2) 0.0357(7) Uani 1 1 d . . . . .
H8A H 0.173321 -0.039851 0.877546 0.054 Uiso 1 1 calc R U . . .
H8B H 0.229502 -0.041471 0.971898 0.054 Uiso 1 1 calc R U . . .
H8C H 0.353385 -0.054109 0.893903 0.054 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
Zr1 O10 2.0322(17) . ?
Zr1 O2 2.0367(17) . ?
Zr1 N19 2.119(2) . ?
Zr1 N22 2.126(2) . ?
Zr1 N5 2.414(2) . ?
Zr1 N13 2.419(2) . ?
O2 C3 1.404(3) . ?
O10 C11 1.404(3) . ?
N19 C20 1.453(3) . ?
N19 C18 1.459(3) . ?
N22 C21 1.448(3) . ?
N22 C23 1.453(3) . ?
N5 C9 1.472(4) . ?
N5 C6 1.475(3) . ?
N5 C4 1.482(3) . ?
N13 C14 1.476(3) . ?
N13 C17 1.477(3) . ?
N13 C12 1.487(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C11 C16 1.535(4) . ?
C11 C15 1.538(4) . ?
C11 C12 1.542(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C3 C8 1.533(4) . ?
C3 C7 1.538(4) . ?
C3 C4 1.542(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

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
O10 Zr1 O2 101.92(7) . . ?
O10 Zr1 N19 154.75(7) . . ?
O2 Zr1 N19 90.94(7) . . ?
O10 Zr1 N22 89.62(8) . . ?
O2 Zr1 N22 154.54(8) . . ?
N19 Zr1 N22 87.66(8) . . ?
O10 Zr1 N5 90.68(7) . . ?
O2 Zr1 N5 71.53(7) . . ?
N19 Zr1 N5 114.13(7) . . ?
N22 Zr1 N5 85.88(8) . . ?
O10 Zr1 N13 71.98(7) . . ?
O2 Zr1 N13 88.99(7) . . ?
N19 Zr1 N13 86.80(7) . . ?
N22 Zr1 N13 116.29(8) . . ?
N5 Zr1 N13 150.91(7) . . ?
C3 O2 Zr1 130.09(16) . . ?
C11 O10 Zr1 129.81(15) . . ?
C20 N19 C18 108.50(19) . . ?
C20 N19 Zr1 126.41(15) . . ?
C18 N19 Zr1 124.50(16) . . ?
C21 N22 C23 108.4(2) . . ?
C21 N22 Zr1 125.69(16) . . ?
C23 N22 Zr1 125.45(17) . . ?
C9 N5 C6 109.1(2) . . ?
C9 N5 C4 109.2(2) . . ?
C6 N5 C4 111.6(2) . . ?
C9 N5 Zr1 112.94(16) . . ?
C6 N5 Zr1 107.76(16) . . ?
C4 N5 Zr1 106.19(15) . . ?
C14 N13 C17 108.9(2) . . ?
C14 N13 C12 111.78(19) . . ?
C17 N13 C12 109.1(2) . . ?
C14 N13 Zr1 109.11(15) . . ?
C17 N13 Zr1 112.27(15) . . ?
C12 N13 Zr1 105.70(14) . . ?
N19 C18 H18A 109.5 . . ?
N19 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N19 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N19 C20 H20A 109.5 . . ?
N19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O10 C11 C16 109.3(2) . . ?
O10 C11 C15 110.1(2) . . ?
C16 C11 C15 108.2(2) . . ?
O10 C11 C12 107.0(2) . . ?
C16 C11 C12 108.1(2) . . ?
C15 C11 C12 114.0(2) . . ?
N22 C21 H21A 109.5 . . ?
N22 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N22 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N13 C14 H14A 109.5 . . ?
N13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N13 C17 H17A 109.5 . . ?
N13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O2 C3 C8 109.7(2) . . ?
O2 C3 C7 110.4(2) . . ?
C8 C3 C7 107.6(2) . . ?
O2 C3 C4 106.8(2) . . ?
C8 C3 C4 108.2(2) . . ?
C7 C3 C4 114.1(2) . . ?
N13 C12 C11 112.3(2) . . ?
N13 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
N13 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
N5 C6 H6A 109.5 . . ?
N5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N5 C4 C3 112.6(2) . . ?
N5 C4 H4A 109.1 . . ?
C3 C4 H4A 109.1 . . ?
N5 C4 H4B 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N22 C23 H23A 109.5 . . ?
N22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N5 C9 H9A 109.5 . . ?
N5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

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
Zr1 O10 C11 C16 -125.1(2) . . . . ?
Zr1 O10 C11 C15 116.1(2) . . . . ?
Zr1 O10 C11 C12 -8.3(3) . . . . ?
Zr1 O2 C3 C8 -121.8(2) . . . . ?
Zr1 O2 C3 C7 119.7(2) . . . . ?
Zr1 O2 C3 C4 -4.8(3) . . . . ?
C14 N13 C12 C11 79.3(3) . . . . ?
C17 N13 C12 C11 -160.2(2) . . . . ?
Zr1 N13 C12 C11 -39.3(2) . . . . ?
O10 C11 C12 N13 33.2(3) . . . . ?
C16 C11 C12 N13 150.7(2) . . . . ?
C15 C11 C12 N13 -88.8(3) . . . . ?
C9 N5 C4 C3 -160.8(2) . . . . ?
C6 N5 C4 C3 78.5(3) . . . . ?
Zr1 N5 C4 C3 -38.7(2) . . . . ?
O2 C3 C4 N5 30.8(3) . . . . ?
C8 C3 C4 N5 148.8(2) . . . . ?
C7 C3 C4 N5 -91.4(3) . . . . ?

_refine_diff_density_max         0.723
_refine_diff_density_min         -0.886
_refine_diff_density_rms         0.087


_chemical_properties_physical    Air-sensitive,Oxygen-sensitive
####################################################################### 
# 
# 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_ysh-j-1
_database_code_depnum_ccdc_archive 'CCDC 2036183'
loop_
_audit_author_name
_audit_author_address
'Jianwei Jiang'
;Chung Ang University
South Korea
;
_audit_update_record             
;
2020-10-09 deposited with the CCDC.	2022-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H48 N4 O2 Zr'
_chemical_formula_sum            'C22 H48 N4 O2 Zr'
_chemical_formula_weight         491.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zr Zr -0.1862 2.2449 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.9734(3)
_cell_length_b                   9.57200(19)
_cell_length_c                   16.6128(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.5782(16)
_cell_angle_gamma                90
_cell_volume                     2539.09(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    20701
_cell_measurement_theta_min      5.327
_cell_measurement_theta_max      79.037

_exptl_crystal_description       cube
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.133
_exptl_crystal_size_mid          0.067
_exptl_crystal_size_min          0.054
_exptl_absorpt_coefficient_mu    3.719
_shelx_estimated_absorpt_T_min   0.638
_shelx_estimated_absorpt_T_max   0.824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.70240
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'SCALE3 ABSPACK'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20701
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         5.327
_diffrn_reflns_theta_max         79.037
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5328
_reflns_number_gt                4797
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _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.
;

_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0519P)²+12.1914P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5328
_refine_ls_number_parameters     270
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1322
_refine_ls_wR_factor_gt          0.1307
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.111
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.79322(2) 0.82741(3) 0.12109(2) 0.01312(11) Uani 1 1 d . . . . .
O1 O 0.76198(17) 0.9626(3) 0.21055(14) 0.0168(5) Uani 1 1 d . . . . .
C7 C 0.8313(3) 0.8252(4) 0.3100(2) 0.0187(8) Uani 1 1 d . . . . .
H7A H 0.8712 0.8375 0.3561 0.022 Uiso 1 1 calc R U . . .
H7B H 0.7889 0.7557 0.3257 0.022 Uiso 1 1 calc R U . . .
C1 C 0.7877(2) 0.9650(4) 0.2918(2) 0.0141(7) Uani 1 1 d . . . . .
C6 C 0.8426(2) 1.0940(4) 0.3096(2) 0.0196(8) Uani 1 1 d . . . . .
H6A H 0.8670 1.0863 0.3649 0.024 Uiso 1 1 calc R U . . .
H6B H 0.8893 1.0957 0.2717 0.024 Uiso 1 1 calc R U . . .
C2 C 0.7112(2) 0.9708(4) 0.3463(2) 0.0185(7) Uani 1 1 d . . . . .
H2A H 0.6727 0.8933 0.3315 0.022 Uiso 1 1 calc R U . . .
H2B H 0.7303 0.9564 0.4029 0.022 Uiso 1 1 calc R U . . .
C3 C 0.6632(3) 1.1081(5) 0.3403(2) 0.0260(9) Uani 1 1 d . . . . .
H3A H 0.6169 1.1071 0.3788 0.031 Uiso 1 1 calc R U . . .
H3B H 0.6384 1.1183 0.2854 0.031 Uiso 1 1 calc R U . . .
C4 C 0.7206(3) 1.2318(5) 0.3589(3) 0.0274(9) Uani 1 1 d . . . . .
H4A H 0.6889 1.3201 0.3524 0.033 Uiso 1 1 calc R U . . .
H4B H 0.7419 1.2261 0.4153 0.033 Uiso 1 1 calc R U . . .
C5 C 0.7937(3) 1.2309(4) 0.3021(2) 0.0255(9) Uani 1 1 d . . . . .
H5A H 0.8315 1.3103 0.3151 0.031 Uiso 1 1 calc R U . . .
H5B H 0.7725 1.2425 0.2460 0.031 Uiso 1 1 calc R U . . .
N1 N 0.8773(2) 0.7708(3) 0.23963(18) 0.0181(6) Uani 1 1 d . . . . .
C9 C 0.9609(3) 0.8345(5) 0.2339(3) 0.0263(9) Uani 1 1 d . . . . .
H9A H 0.9913 0.8251 0.2856 0.039 Uiso 1 1 calc R U . . .
H9B H 0.9550 0.9336 0.2202 0.039 Uiso 1 1 calc R U . . .
H9C H 0.9921 0.7869 0.1919 0.039 Uiso 1 1 calc R U . . .
C8 C 0.8883(3) 0.6178(4) 0.2501(2) 0.0251(9) Uani 1 1 d . . . . .
H8A H 0.9223 0.5811 0.2066 0.038 Uiso 1 1 calc R U . . .
H8B H 0.8334 0.5722 0.2485 0.038 Uiso 1 1 calc R U . . .
H8C H 0.9166 0.5991 0.3021 0.038 Uiso 1 1 calc R U . . .
O2 O 0.70638(16) 0.6746(3) 0.13711(16) 0.0176(5) Uani 1 1 d . . . . .
C10 C 0.6197(2) 0.6806(4) 0.1275(2) 0.0167(7) Uani 1 1 d . . . . .
C16 C 0.5959(2) 0.8317(4) 0.1029(2) 0.0184(8) Uani 1 1 d . . . . .
H16A H 0.5432 0.8298 0.0700 0.022 Uiso 1 1 calc R U . . .
H16B H 0.5856 0.8870 0.1520 0.022 Uiso 1 1 calc R U . . .
C13 C 0.5633(3) 0.3942(5) 0.1752(3) 0.0339(10) Uani 1 1 d . . . . .
H13A H 0.5767 0.2984 0.1940 0.041 Uiso 1 1 calc R U . . .
H13B H 0.5017 0.4019 0.1683 0.041 Uiso 1 1 calc R U . . .
C11 C 0.5880(3) 0.5701(4) 0.0664(2) 0.0227(8) Uani 1 1 d . . . . .
H11A H 0.5271 0.5831 0.0565 0.027 Uiso 1 1 calc R U . . .
H11B H 0.6162 0.5844 0.0148 0.027 Uiso 1 1 calc R U . . .
C15 C 0.5790(3) 0.6501(5) 0.2087(2) 0.0231(8) Uani 1 1 d . . . . .
H15A H 0.6016 0.7163 0.2496 0.028 Uiso 1 1 calc R U . . .
H15B H 0.5179 0.6661 0.2031 0.028 Uiso 1 1 calc R U . . .
C12 C 0.6041(3) 0.4207(4) 0.0954(3) 0.0270(9) Uani 1 1 d . . . . .
H12A H 0.5815 0.3541 0.0547 0.032 Uiso 1 1 calc R U . . .
H12B H 0.6652 0.4047 0.1014 0.032 Uiso 1 1 calc R U . . .
C14 C 0.5947(3) 0.5003(5) 0.2380(3) 0.0315(10) Uani 1 1 d . . . . .
H14A H 0.6555 0.4864 0.2487 0.038 Uiso 1 1 calc R U . . .
H14B H 0.5655 0.4851 0.2891 0.038 Uiso 1 1 calc R U . . .
N2 N 0.6616(2) 0.9006(3) 0.05659(19) 0.0189(7) Uani 1 1 d . . . . .
C18 C 0.6482(3) 1.0534(4) 0.0596(3) 0.0253(9) Uani 1 1 d . . . . .
H18A H 0.5929 1.0759 0.0361 0.038 Uiso 1 1 calc R U . . .
H18B H 0.6915 1.1005 0.0289 0.038 Uiso 1 1 calc R U . . .
H18C H 0.6514 1.0850 0.1157 0.038 Uiso 1 1 calc R U . . .
C17 C 0.6597(3) 0.8556(5) -0.0285(2) 0.0253(9) Uani 1 1 d . . . . .
H17A H 0.6759 0.7570 -0.0317 0.038 Uiso 1 1 calc R U . . .
H17B H 0.6990 0.9124 -0.0589 0.038 Uiso 1 1 calc R U . . .
H17C H 0.6030 0.8674 -0.0515 0.038 Uiso 1 1 calc R U . . .
N3 N 0.8678(2) 0.6754(3) 0.06169(19) 0.0168(6) Uani 1 1 d . . . . .
C20 C 0.8480(3) 0.5276(4) 0.0536(2) 0.0225(8) Uani 1 1 d . . . . .
H20A H 0.8569 0.4978 -0.0019 0.034 Uiso 1 1 calc R U . . .
H20B H 0.7893 0.5121 0.0669 0.034 Uiso 1 1 calc R U . . .
H20C H 0.8844 0.4735 0.0904 0.034 Uiso 1 1 calc R U . . .
C19 C 0.9543(2) 0.6944(4) 0.0389(2) 0.0219(8) Uani 1 1 d . . . . .
H19A H 0.9911 0.6382 0.0743 0.033 Uiso 1 1 calc R U . . .
H19B H 0.9695 0.7932 0.0441 0.033 Uiso 1 1 calc R U . . .
H19C H 0.9606 0.6644 -0.0170 0.033 Uiso 1 1 calc R U . . .
N4 N 0.8497(2) 0.9868(3) 0.05291(18) 0.0182(6) Uani 1 1 d . . . . .
C21 C 0.8639(3) 1.1302(4) 0.0791(2) 0.0230(8) Uani 1 1 d . . . . .
H21A H 0.9234 1.1533 0.0745 0.035 Uiso 1 1 calc R U . . .
H21B H 0.8478 1.1401 0.1353 0.035 Uiso 1 1 calc R U . . .
H21C H 0.8302 1.1936 0.0451 0.035 Uiso 1 1 calc R U . . .
C22 C 0.8698(3) 0.9759(4) -0.0320(2) 0.0231(8) Uani 1 1 d . . . . .
H22A H 0.8342 1.0400 -0.0636 0.035 Uiso 1 1 calc R U . . .
H22B H 0.8601 0.8799 -0.0505 0.035 Uiso 1 1 calc R U . . .
H22C H 0.9288 1.0005 -0.0388 0.035 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
Zr1 O2 2.038(3) . ?
Zr1 O1 2.043(2) . ?
Zr1 N4 2.117(3) . ?
Zr1 N3 2.139(3) . ?
Zr1 N1 2.415(3) . ?
Zr1 N2 2.437(3) . ?
O1 C1 1.401(4) . ?
C7 N1 1.491(5) . ?
C7 C1 1.535(5) . ?
C1 C6 1.539(5) . ?
C1 C2 1.542(5) . ?
C6 C5 1.529(6) . ?
C2 C3 1.523(6) . ?
C3 C4 1.525(6) . ?
C4 C5 1.521(6) . ?
N1 C9 1.473(5) . ?
N1 C8 1.485(5) . ?
O2 C10 1.391(4) . ?
C10 C15 1.541(5) . ?
C10 C11 1.541(5) . ?
C10 C16 1.547(5) . ?
C16 N2 1.473(5) . ?
C13 C12 1.515(6) . ?
C13 C14 1.531(7) . ?
C11 C12 1.529(6) . ?
C15 C14 1.533(6) . ?
N2 C17 1.478(5) . ?
N2 C18 1.479(5) . ?
N3 C19 1.454(5) . ?
N3 C20 1.455(5) . ?
N4 C21 1.456(5) . ?
N4 C22 1.458(5) . ?

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
O2 Zr1 O1 100.30(11) . . ?
O2 Zr1 N4 152.71(12) . . ?
O1 Zr1 N4 92.81(11) . . ?
O2 Zr1 N3 87.81(11) . . ?
O1 Zr1 N3 156.48(11) . . ?
N4 Zr1 N3 89.56(12) . . ?
O2 Zr1 N1 95.62(11) . . ?
O1 Zr1 N1 71.97(10) . . ?
N4 Zr1 N1 111.23(12) . . ?
N3 Zr1 N1 85.37(11) . . ?
O2 Zr1 N2 71.43(11) . . ?
O1 Zr1 N2 84.98(10) . . ?
N4 Zr1 N2 86.15(12) . . ?
N3 Zr1 N2 118.53(11) . . ?
N1 Zr1 N2 151.31(11) . . ?
C1 O1 Zr1 129.8(2) . . ?
N1 C7 C1 112.4(3) . . ?
O1 C1 C7 107.2(3) . . ?
O1 C1 C6 110.4(3) . . ?
C7 C1 C6 114.1(3) . . ?
O1 C1 C2 110.5(3) . . ?
C7 C1 C2 106.2(3) . . ?
C6 C1 C2 108.3(3) . . ?
C5 C6 C1 112.7(3) . . ?
C3 C2 C1 113.5(3) . . ?
C2 C3 C4 111.0(3) . . ?
C5 C4 C3 109.8(3) . . ?
C4 C5 C6 110.7(3) . . ?
C9 N1 C8 108.1(3) . . ?
C9 N1 C7 111.9(3) . . ?
C8 N1 C7 108.2(3) . . ?
C9 N1 Zr1 109.8(2) . . ?
C8 N1 Zr1 112.2(2) . . ?
C7 N1 Zr1 106.6(2) . . ?
C10 O2 Zr1 129.4(2) . . ?
O2 C10 C15 109.5(3) . . ?
O2 C10 C11 110.8(3) . . ?
C15 C10 C11 107.9(3) . . ?
O2 C10 C16 107.8(3) . . ?
C15 C10 C16 107.6(3) . . ?
C11 C10 C16 113.2(3) . . ?
N2 C16 C10 112.5(3) . . ?
C12 C13 C14 110.2(4) . . ?
C12 C11 C10 112.7(3) . . ?
C14 C15 C10 112.7(3) . . ?
C13 C12 C11 111.1(4) . . ?
C13 C14 C15 110.9(4) . . ?
C16 N2 C17 111.9(3) . . ?
C16 N2 C18 108.6(3) . . ?
C17 N2 C18 108.7(3) . . ?
C16 N2 Zr1 105.1(2) . . ?
C17 N2 Zr1 109.3(2) . . ?
C18 N2 Zr1 113.2(2) . . ?
C19 N3 C20 107.6(3) . . ?
C19 N3 Zr1 125.5(2) . . ?
C20 N3 Zr1 125.6(3) . . ?
C21 N4 C22 108.7(3) . . ?
C21 N4 Zr1 125.8(2) . . ?
C22 N4 Zr1 125.0(2) . . ?

_refine_diff_density_max         0.861
_refine_diff_density_min         -1.531
_refine_diff_density_rms         0.117

_shelxl_version_number           2013-4

