# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2095325'
loop_
_audit_author_name
_audit_author_address
'Dr. Andrew G. Sykes'
;University of South Dakota
United States of America
;
_audit_update_record             
;
2021-07-08 deposited with the CCDC.	2021-09-27 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         'C12 H18 N2 O5'
_chemical_formula_sum            'C12 H18 N2 O5'
_chemical_formula_weight         270.28

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'

_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                   7.5493(3)
_cell_length_b                   9.2659(3)
_cell_length_c                   9.8603(3)
_cell_angle_alpha                91.084(2)
_cell_angle_beta                 104.5860(10)
_cell_angle_gamma                109.5870(10)
_cell_volume                     624.83(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2534
_cell_measurement_theta_min      4.7
_cell_measurement_theta_max      74.3

_exptl_crystal_description       Plate
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_F_000             288
_exptl_transmission_factor_min   0.967
_exptl_transmission_factor_max   0.981
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.946
_shelx_estimated_absorpt_T_min   0.911
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19191
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.664
_diffrn_reflns_theta_max         74.298
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2534
_reflns_number_gt                2269
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_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)+(0.0854P)²+0.4133P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2534
_refine_ls_number_parameters     200
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1492
_refine_ls_wR_factor_gt          0.1446
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.111
_refine_ls_shift/su_max          0.000
_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
O2 O 0.48173(18) 0.34027(14) 0.79731(13) 0.0188(3) Uani 1 1 d D . . . .
H2 H 0.532926 0.309259 0.741876 0.028 Uiso 1 1 calc R U . . .
O1 O 0.33890(17) 0.69383(13) 0.40735(12) 0.0147(3) Uani 1 1 d . . . . .
N2 N 0.5192(2) 0.76273(16) 0.67406(15) 0.0125(3) Uani 1 1 d . . . . .
N1 N 0.0197(2) 0.29801(17) 0.35545(16) 0.0170(3) Uani 1 1 d . . . . .
C6 C 0.0415(3) 0.4848(2) 0.18452(19) 0.0202(4) Uani 1 1 d . . . . .
H6A H 0.137339 0.484549 0.133543 0.030 Uiso 1 1 calc R U . . .
H6B H 0.033621 0.588039 0.191079 0.030 Uiso 1 1 calc R U . . .
H6C H -0.086904 0.410262 0.133855 0.030 Uiso 1 1 calc R U . . .
C5 C 0.1034(2) 0.44132(19) 0.32997(18) 0.0151(4) Uani 1 1 d . . . . .
C4 C 0.2550(2) 0.55533(18) 0.43721(18) 0.0129(4) Uani 1 1 d . . . . .
C3 C 0.3047(2) 0.50840(19) 0.57391(18) 0.0132(4) Uani 1 1 d . . . . .
C8 C 0.4318(2) 0.62131(19) 0.69132(18) 0.0129(3) Uani 1 1 d . . . . .
C9 C 0.6220(2) 0.89489(18) 0.78371(17) 0.0130(4) Uani 1 1 d D . . . .
C10 C 0.7899(2) 1.00341(19) 0.73268(18) 0.0157(4) Uani 1 1 d . . . . .
H10A H 0.847701 1.103235 0.793276 0.019 Uiso 1 1 calc R U . . .
H10B H 0.893090 0.957932 0.741152 0.019 Uiso 1 1 calc R U . . .
C11 C 0.4745(2) 0.97365(19) 0.79188(18) 0.0163(4) Uani 1 1 d . . . . .
H11A H 0.542693 1.071224 0.855537 0.020 Uiso 1 1 calc R U . . .
H11B H 0.419774 0.999062 0.697018 0.020 Uiso 1 1 calc R U . . .
C2 C 0.2198(2) 0.35246(19) 0.59620(18) 0.0143(4) Uani 1 1 d . . . . .
C7 C 0.2765(3) 0.2927(2) 0.73626(19) 0.0181(4) Uani 1 1 d D . . . .
H7A H 0.217485 0.328827 0.802838 0.022 Uiso 1 1 calc R U . . .
H7B H 0.221180 0.178661 0.722782 0.022 Uiso 1 1 calc R U . . .
C1 C 0.0806(3) 0.2535(2) 0.48414(19) 0.0164(4) Uani 1 1 d . . . . .
H1 H 0.024178 0.148379 0.497577 0.020 Uiso 1 1 calc R U . . .
C12 C 0.712(2) 0.8372(18) 0.9231(16) 0.015(2) Uani 0.489(5) 1 d D . P A 1
H12A H 0.608006 0.774655 0.963840 0.018 Uiso 0.489(5) 1 calc R U P A 1
H12B H 0.787351 0.773114 0.904591 0.018 Uiso 0.489(5) 1 calc R U P A 1
O5 O 0.8389(3) 0.9721(3) 1.0182(2) 0.0161(8) Uani 0.489(5) 1 d D . P A 1
H5 H 0.936069 1.016925 0.988415 0.024 Uiso 0.489(5) 1 calc R U P A 1
C12' C 0.688(3) 0.853(2) 0.9312(16) 0.016(2) Uani 0.511(5) 1 d D . P A 2
H12C H 0.754367 0.948002 0.997722 0.019 Uiso 0.511(5) 1 calc R U P A 2
H12D H 0.571129 0.789906 0.959924 0.019 Uiso 0.511(5) 1 calc R U P A 2
O5' O 0.8166(4) 0.7681(3) 0.9408(3) 0.0178(7) Uani 0.511(5) 1 d D . P A 2
H5' H 0.915776 0.820678 0.916485 0.027 Uiso 0.511(5) 1 calc R U P A 2
O4 O 0.72330(18) 1.02890(14) 0.59026(13) 0.0179(3) Uani 1 1 d . . . . .
H4 H 0.636938 1.068745 0.583172 0.027 Uiso 1 1 calc R U . . .
O3 O 0.32046(18) 0.87769(16) 0.84213(14) 0.0228(3) Uani 1 1 d . . . . .
H3 H 0.241448 0.922860 0.844492 0.034 Uiso 1 1 calc R U . . .
H8 H 0.451(3) 0.592(3) 0.781(2) 0.016(5) Uiso 1 1 d . . . . .
H2' H 0.499(4) 0.780(3) 0.582(3) 0.034(7) Uiso 1 1 d . . . . .


_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
O2 C7 1.421(2) . ?
O2 H2 0.8400 . ?
O1 C4 1.303(2) . ?
N2 C8 1.291(2) . ?
N2 C9 1.470(2) . ?
N2 H2' 0.91(3) . ?
N1 C5 1.325(2) . ?
N1 C1 1.358(2) . ?
C6 C5 1.499(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C5 C4 1.443(2) . ?
C4 C3 1.422(2) . ?
C3 C2 1.417(2) . ?
C3 C8 1.441(2) . ?
C8 H8 0.92(2) . ?
C9 C12' 1.518(15) . ?
C9 C10 1.535(2) . ?
C9 C11 1.538(2) . ?
C9 C12 1.562(15) . ?
C10 O4 1.420(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 O3 1.415(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C2 C1 1.377(2) . ?
C2 C7 1.512(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C1 H1 0.9500 . ?
C12 O5 1.434(15) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
O5 H5 0.8400 . ?
C12' O5' 1.426(14) . ?
C12' H12C 0.9900 . ?
C12' H12D 0.9900 . ?
O5' H5' 0.8400 . ?
O4 H4 0.8400 . ?
O3 H3 0.8400 . ?

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
C7 O2 H2 109.5 . . ?
C8 N2 C9 127.37(14) . . ?
C8 N2 H2' 113.3(17) . . ?
C9 N2 H2' 118.9(17) . . ?
C5 N1 C1 120.02(15) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C5 C4 121.88(16) . . ?
N1 C5 C6 118.88(15) . . ?
C4 C5 C6 119.22(15) . . ?
O1 C4 C3 122.97(15) . . ?
O1 C4 C5 120.32(15) . . ?
C3 C4 C5 116.71(15) . . ?
C2 C3 C4 120.00(15) . . ?
C2 C3 C8 120.01(15) . . ?
C4 C3 C8 119.88(15) . . ?
N2 C8 C3 121.69(15) . . ?
N2 C8 H8 119.3(14) . . ?
C3 C8 H8 119.0(14) . . ?
N2 C9 C12' 114.6(7) . . ?
N2 C9 C10 106.31(13) . . ?
C12' C9 C10 113.6(7) . . ?
N2 C9 C11 106.80(13) . . ?
C12' C9 C11 105.2(6) . . ?
C10 C9 C11 110.16(13) . . ?
N2 C9 C12 108.9(6) . . ?
C10 C9 C12 108.3(7) . . ?
C11 C9 C12 116.0(6) . . ?
O4 C10 C9 111.23(13) . . ?
O4 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
O4 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
O3 C11 C9 111.44(14) . . ?
O3 C11 H11A 109.3 . . ?
C9 C11 H11A 109.3 . . ?
O3 C11 H11B 109.3 . . ?
C9 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C1 C2 C3 117.56(16) . . ?
C1 C2 C7 119.78(15) . . ?
C3 C2 C7 122.66(15) . . ?
O2 C7 C2 113.76(14) . . ?
O2 C7 H7A 108.8 . . ?
C2 C7 H7A 108.8 . . ?
O2 C7 H7B 108.8 . . ?
C2 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
N1 C1 C2 123.53(16) . . ?
N1 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
O5 C12 C9 106.7(10) . . ?
O5 C12 H12A 110.4 . . ?
C9 C12 H12A 110.4 . . ?
O5 C12 H12B 110.4 . . ?
C9 C12 H12B 110.4 . . ?
H12A C12 H12B 108.6 . . ?
C12 O5 H5 109.5 . . ?
O5' C12' C9 112.8(11) . . ?
O5' C12' H12C 109.0 . . ?
C9 C12' H12C 109.0 . . ?
O5' C12' H12D 109.0 . . ?
C9 C12' H12D 109.0 . . ?
H12C C12' H12D 107.8 . . ?
C12' O5' H5' 109.5 . . ?
C10 O4 H4 109.5 . . ?
C11 O3 H3 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
C1 N1 C5 C4 -2.1(3) . . . . ?
C1 N1 C5 C6 176.42(15) . . . . ?
N1 C5 C4 O1 177.65(14) . . . . ?
C6 C5 C4 O1 -0.9(2) . . . . ?
N1 C5 C4 C3 -2.7(2) . . . . ?
C6 C5 C4 C3 178.70(14) . . . . ?
O1 C4 C3 C2 -174.54(14) . . . . ?
C5 C4 C3 C2 5.9(2) . . . . ?
O1 C4 C3 C8 9.3(2) . . . . ?
C5 C4 C3 C8 -170.29(14) . . . . ?
C9 N2 C8 C3 167.78(15) . . . . ?
C2 C3 C8 N2 176.55(15) . . . . ?
C4 C3 C8 N2 -7.3(2) . . . . ?
C8 N2 C9 C12' 21.2(7) . . . . ?
C8 N2 C9 C10 147.58(16) . . . . ?
C8 N2 C9 C11 -94.81(19) . . . . ?
C8 N2 C9 C12 31.1(7) . . . . ?
N2 C9 C10 O4 48.08(17) . . . . ?
C12' C9 C10 O4 175.1(6) . . . . ?
C11 C9 C10 O4 -67.28(17) . . . . ?
C12 C9 C10 O4 165.0(6) . . . . ?
N2 C9 C11 O3 66.44(17) . . . . ?
C12' C9 C11 O3 -55.8(7) . . . . ?
C10 C9 C11 O3 -178.50(13) . . . . ?
C12 C9 C11 O3 -55.2(7) . . . . ?
C4 C3 C2 C1 -4.2(2) . . . . ?
C8 C3 C2 C1 171.95(15) . . . . ?
C4 C3 C2 C7 175.72(14) . . . . ?
C8 C3 C2 C7 -8.1(2) . . . . ?
C1 C2 C7 O2 133.17(16) . . . . ?
C3 C2 C7 O2 -46.7(2) . . . . ?
C5 N1 C1 C2 4.1(3) . . . . ?
C3 C2 C1 N1 -0.9(3) . . . . ?
C7 C2 C1 N1 179.21(15) . . . . ?
N2 C9 C12 O5 169.9(7) . . . . ?
C10 C9 C12 O5 54.7(11) . . . . ?
C11 C9 C12 O5 -69.6(11) . . . . ?
N2 C9 C12' O5' 59.1(13) . . . . ?
C10 C9 C12' O5' -63.4(12) . . . . ?
C11 C9 C12' O5' 176.0(9) . . . . ?

_refine_diff_density_max         0.731
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.073


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol, Diethylether'
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2095330'
loop_
_audit_author_name
_audit_author_address
'Dr. Andrew G. Sykes'
;University of South Dakota
United States of America
;
_audit_update_record             
;
2021-07-08 deposited with the CCDC.	2021-09-27 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT417_shelx               
;
PROBLEM: Short Inter D-H..H-D       H4       ..H9       .       1.20 Ang.
RESPONSE: These alerts are all related to the hydrogen atoms of lattice water.
;
_vrf_PLAT417_shelx_2             
;
PROBLEM: Short Inter D-H..H-D       H5'      ..H100     .       1.57 Ang.
RESPONSE: These alerts are all related to the hydrogen atoms of lattice water.
;
_vrf_PLAT417_shelx_3             
;
PROBLEM: Short Inter D-H..H-D       H101     ..H102     .       1.96 Ang.
RESPONSE: These alerts are all related to the hydrogen atoms of lattice water.
;
# Added during the CSD deposition process: Thursday 08 July 2021 07:22 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H34 N4 O10 Zn, 5(H2 O)'
_chemical_formula_sum            'C24 H44 N4 O15 Zn'
_chemical_formula_weight         694.00

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   20.3659(17)
_cell_length_b                   8.7855(9)
_cell_length_c                   16.9217(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3027.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    106(2)
_cell_measurement_reflns_used    23510
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      25.4

_exptl_crystal_description       Rectangle
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_F_000             1464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.070
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.889
_shelx_estimated_absorpt_T_min   0.940
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5546
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      106(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23510
_diffrn_reflns_av_unetI/netI     0.1097
_diffrn_reflns_av_R_equivalents  0.1272
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.000
_diffrn_reflns_theta_max         25.359
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             5476
_reflns_number_gt                3725
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.904
_reflns_Friedel_fraction_max     0.973
_reflns_Friedel_fraction_full    0.973

_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_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)+(0.0631P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1246 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5476
_refine_ls_number_parameters     455
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1013
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1505
_refine_ls_wR_factor_gt          0.1257
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.091
_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
Zn01 Zn 0.24767(5) 0.65303(9) 0.49748(14) 0.0122(2) Uani 1 1 d . . . . .
O6 O 0.2478(3) 0.8142(11) 0.4121(6) 0.015(2) Uani 1 1 d . . . . .
O8 O 0.2103(4) 0.5062(9) 0.5889(6) 0.0196(18) Uani 1 1 d . . . . .
O9 O 0.0561(3) 0.7944(8) 0.5310(6) 0.024(2) Uani 1 1 d . . . . .
H9 H 0.022539 0.762297 0.507492 0.036 Uiso 1 1 calc R U . . .
O10 O 0.0600(3) 0.3333(8) 0.4398(5) 0.0195(18) Uani 1 1 d . . . . .
H10 H 0.084184 0.268833 0.462121 0.029 Uiso 1 1 calc R U . . .
O3 O 0.2763(3) 0.4832(8) 0.4111(5) 0.0198(19) Uani 1 1 d . . . . .
O4 O 0.4418(3) 0.7600(8) 0.4471(5) 0.0216(19) Uani 1 1 d . . . . .
H4 H 0.476236 0.720029 0.464988 0.032 Uiso 1 1 calc R U . . .
O1 O 0.2546(3) 0.8177(11) 0.5829(6) 0.016(2) Uani 1 1 d . . . . .
O2 O 0.4777(3) 0.6090(8) 0.7260(5) 0.0178(18) Uani 1 1 d . . . . .
H2 H 0.488631 0.696640 0.740793 0.027 Uiso 1 1 calc R U . . .
O7 O 0.0275(3) 0.6200(8) 0.2546(6) 0.024(2) Uani 1 1 d . . . . .
H7 H 0.017784 0.706875 0.237372 0.036 Uiso 1 1 calc R U . . .
O104 O 0.5251(4) 0.3530(9) 0.6602(6) 0.024(2) Uani 1 1 d D . . . .
O102 O 0.1040(4) 1.0843(8) 0.5265(5) 0.0256(19) Uani 1 1 d . . . . .
O103 O 0.5243(4) 0.8446(10) 0.8110(6) 0.026(2) Uani 1 1 d D . . . .
O5 O 0.4309(3) 0.3093(8) 0.5451(5) 0.0200(18) Uani 1 1 d . . . . .
H5' H 0.406082 0.246568 0.522475 0.030 Uiso 1 1 calc R U . . .
N4 N 0.1512(4) 0.6076(9) 0.4600(6) 0.012(2) Uani 1 1 d . . . . .
O101 O 0.2370(4) 1.0717(8) 0.5037(8) 0.028(2) Uani 1 1 d D . . . .
N1 N 0.2773(4) 0.8404(10) 0.7923(6) 0.017(2) Uani 1 1 d . . . . .
N2 N 0.3448(4) 0.5941(10) 0.5295(7) 0.016(2) Uani 1 1 d . . . . .
O100 O 0.3826(4) 1.0096(11) 0.5075(7) 0.041(2) Uani 1 1 d . . . . .
N3 N 0.2313(5) 0.8482(10) 0.2030(6) 0.015(2) Uani 1 1 d . . . . .
C1 C 0.2544(4) 0.8616(14) 0.7202(9) 0.014(3) Uani 1 1 d . . . . .
C13 C 0.2225(5) 0.7941(12) 0.3428(7) 0.013(3) Uani 1 1 d . . . . .
C22 C 0.0465(4) 0.4546(10) 0.4930(9) 0.016(2) Uani 1 1 d . . . . .
H22A H 0.023102 0.412969 0.539532 0.020 Uiso 1 1 calc R U . . .
H22B H 0.016739 0.527758 0.466704 0.020 Uiso 1 1 calc R U . . .
C19 C 0.1076(5) 0.5406(11) 0.5219(8) 0.017(3) Uani 1 1 d . . . . .
C14 C 0.1667(5) 0.7003(11) 0.3262(8) 0.014(3) Uani 1 1 d . . . . .
C18 C 0.1302(5) 0.6272(11) 0.3898(8) 0.014(3) Uani 1 1 d . . . . .
C15 C 0.1461(5) 0.6817(12) 0.2476(7) 0.015(3) Uani 1 1 d . . . . .
C9 C 0.3362(5) 0.4074(11) 0.4272(8) 0.016(3) Uani 1 1 d . . . . .
H9A H 0.355814 0.369856 0.377298 0.019 Uiso 1 1 calc R U . . .
H9B H 0.328104 0.318899 0.462042 0.019 Uiso 1 1 calc R U . . .
C3 C 0.3356(5) 0.6926(11) 0.6637(8) 0.014(3) Uani 1 1 d . . . . .
C4 C 0.3599(5) 0.6705(12) 0.7422(7) 0.015(3) Uani 1 1 d . . . . .
C17 C 0.0909(5) 0.5759(13) 0.2246(8) 0.019(3) Uani 1 1 d . . . . .
H17A H 0.088533 0.570906 0.166242 0.023 Uiso 1 1 calc R U . . .
H17B H 0.101198 0.472448 0.244164 0.023 Uiso 1 1 calc R U . . .
C5 C 0.3288(5) 0.7448(12) 0.8025(8) 0.017(3) Uani 1 1 d . . . . .
H5 H 0.344284 0.728505 0.854788 0.020 Uiso 1 1 calc R U . . .
C16 C 0.1810(5) 0.7538(12) 0.1884(9) 0.018(3) Uani 1 1 d . . . . .
H16 H 0.168722 0.735788 0.135086 0.022 Uiso 1 1 calc R U . . .
C10 C 0.4033(5) 0.6477(12) 0.4097(8) 0.018(3) Uani 1 1 d . . . . .
H10A H 0.428512 0.603844 0.365075 0.021 Uiso 1 1 calc R U . . .
H10B H 0.363370 0.695871 0.387694 0.021 Uiso 1 1 calc R U . . .
C2 C 0.2813(6) 0.7892(11) 0.6531(8) 0.017(3) Uani 1 1 d . . . . .
C7 C 0.3697(5) 0.6151(12) 0.5989(7) 0.014(3) Uani 1 1 d . . . . .
C011 C 0.1977(5) 0.9706(13) 0.7097(8) 0.022(3) Uani 1 1 d . . . . .
H01A H 0.160349 0.916449 0.686264 0.033 Uiso 1 1 calc R U . . .
H01B H 0.210975 1.053984 0.674747 0.033 Uiso 1 1 calc R U . . .
H01C H 0.184846 1.011904 0.761222 0.033 Uiso 1 1 calc R U . . .
C8 C 0.3827(4) 0.5171(11) 0.4670(7) 0.013(2) Uani 1 1 d . . . . .
C6 C 0.4167(5) 0.5679(12) 0.7620(8) 0.020(3) Uani 1 1 d . . . . .
H6A H 0.422703 0.567394 0.820065 0.024 Uiso 1 1 calc R U . . .
H6B H 0.405475 0.462835 0.745700 0.024 Uiso 1 1 calc R U . . .
C20 C 0.1504(5) 0.4315(12) 0.5682(8) 0.019(3) Uani 1 1 d . . . . .
H20A H 0.127184 0.398552 0.616730 0.023 Uiso 1 1 calc R U . . .
H20B H 0.159891 0.340152 0.535957 0.023 Uiso 1 1 calc R U . . .
C11 C 0.4445(4) 0.4321(11) 0.4930(9) 0.017(2) Uani 1 1 d . . . . .
H11A H 0.467336 0.392406 0.445630 0.021 Uiso 1 1 calc R U . . .
H11B H 0.474498 0.504483 0.519633 0.021 Uiso 1 1 calc R U . . .
C016 C 0.3087(5) 0.9766(13) 0.2907(8) 0.021(3) Uani 1 1 d . . . . .
H01D H 0.348918 0.917082 0.297774 0.032 Uiso 1 1 calc R U . . .
H01E H 0.300495 1.037661 0.338128 0.032 Uiso 1 1 calc R U . . .
H01F H 0.313649 1.044144 0.244950 0.032 Uiso 1 1 calc R U . . .
C21 C 0.0860(5) 0.6714(12) 0.5742(8) 0.021(3) Uani 1 1 d . . . . .
H21A H 0.054344 0.632816 0.613768 0.025 Uiso 1 1 calc R U . . .
H21B H 0.124705 0.710964 0.603094 0.025 Uiso 1 1 calc R U . . .
C12 C 0.2526(5) 0.8724(17) 0.2772(9) 0.019(4) Uani 1 1 d . . . . .
H18' H 0.085(4) 0.614(10) 0.378(6) 0.00(2) Uiso 1 1 d . . . . .
H7' H 0.412(4) 0.563(9) 0.609(6) 0.00(2) Uiso 1 1 d . . . . .
H3' H 0.253(4) 0.422(12) 0.367(7) 0.02(3) Uiso 1 1 d . . . . .
H8' H 0.235(7) 0.435(18) 0.584(11) 0.06(6) Uiso 1 1 d . . . . .
H101 H 0.241(5) 1.003(12) 0.536(7) 0.01(3) Uiso 1 1 d . . . . .
H104 H 0.510(4) 0.432(11) 0.690(7) 0.01(3) Uiso 1 1 d . . . . .
H102 H 0.152(4) 1.085(9) 0.523(6) 0.01(2) Uiso 1 1 d . . . . .
H201 H 0.230(6) 1.020(13) 0.458(4) 0.03(3) Uiso 1 1 d D . . . .
H202 H 0.080(8) 1.01(2) 0.519(14) 0.10(7) Uiso 1 1 d . . . . .
H204 H 0.564(6) 0.33(3) 0.639(14) 0.19(12) Uiso 1 1 d D . . . .
H200 H 0.345(6) 1.004(13) 0.512(9) 0.04(4) Uiso 1 1 d . . . . .
H100 H 0.406(6) 1.078(14) 0.491(9) 0.04(4) Uiso 1 1 d . . . . .
H103 H 0.529(8) 0.937(9) 0.789(10) 0.09(6) Uiso 1 1 d D . . . .
H203 H 0.502(6) 0.803(15) 0.851(6) 0.07(5) Uiso 1 1 d D . . . .


_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
Zn01 O6 2.023(10) . ?
Zn01 O1 2.050(10) . ?
Zn01 N4 2.103(8) . ?
Zn01 N2 2.116(9) . ?
Zn01 O8 2.153(9) . ?
Zn01 O3 2.169(8) . ?
O6 C13 1.293(15) . ?
O8 C20 1.429(12) . ?
O8 H8' 0.80(15) . ?
O9 C21 1.439(13) . ?
O9 H9 0.8400 . ?
O10 C22 1.422(14) . ?
O10 H10 0.8400 . ?
O3 C9 1.417(11) . ?
O3 H3' 1.03(11) . ?
O4 C10 1.410(13) . ?
O4 H4 0.8400 . ?
O1 C2 1.331(16) . ?
O2 C6 1.430(13) . ?
O2 H2 0.8400 . ?
O7 C17 1.440(13) . ?
O7 H7 0.8400 . ?
O104 H104 0.91(10) . ?
O104 H204 0.90(3) . ?
O102 H102 0.97(9) . ?
O102 H202 0.81(18) . ?
O103 H103 0.90(3) . ?
O103 H203 0.89(3) . ?
O5 C11 1.421(13) . ?
O5 H5' 0.8400 . ?
N4 C18 1.274(16) . ?
N4 C19 1.494(14) . ?
O101 H101 0.82(11) . ?
O101 H201 0.91(3) . ?
N1 C1 1.319(18) . ?
N1 C5 1.354(14) . ?
N2 C7 1.292(16) . ?
N2 C8 1.475(14) . ?
O100 H200 0.76(11) . ?
O100 H100 0.81(13) . ?
N3 C16 1.342(14) . ?
N3 C12 1.346(19) . ?
C1 C2 1.412(18) . ?
C1 C011 1.511(15) . ?
C13 C14 1.431(15) . ?
C13 C12 1.443(19) . ?
C22 C19 1.535(14) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C19 C20 1.515(15) . ?
C19 C21 1.516(15) . ?
C14 C15 1.403(17) . ?
C14 C18 1.457(17) . ?
C18 H18' 0.94(9) . ?
C15 C16 1.382(17) . ?
C15 C17 1.510(15) . ?
C9 C8 1.510(14) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C3 C2 1.405(15) . ?
C3 C4 1.431(17) . ?
C3 C7 1.464(17) . ?
C4 C5 1.367(16) . ?
C4 C6 1.505(15) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C5 H5 0.9500 . ?
C16 H16 0.9500 . ?
C10 C8 1.560(15) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C7 H7' 0.99(8) . ?
C011 H01A 0.9800 . ?
C011 H01B 0.9800 . ?
C011 H01C 0.9800 . ?
C8 C11 1.527(13) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C016 C12 1.480(15) . ?
C016 H01D 0.9800 . ?
C016 H01E 0.9800 . ?
C016 H01F 0.9800 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?

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
O6 Zn01 O1 90.5(2) . . ?
O6 Zn01 N4 85.3(3) . . ?
O1 Zn01 N4 114.3(3) . . ?
O6 Zn01 N2 110.7(3) . . ?
O1 Zn01 N2 85.9(3) . . ?
N4 Zn01 N2 154.8(3) . . ?
O6 Zn01 O8 158.9(3) . . ?
O1 Zn01 O8 86.6(4) . . ?
N4 Zn01 O8 76.9(3) . . ?
N2 Zn01 O8 90.0(3) . . ?
O6 Zn01 O3 90.0(4) . . ?
O1 Zn01 O3 160.5(3) . . ?
N4 Zn01 O3 85.2(3) . . ?
N2 Zn01 O3 75.7(3) . . ?
O8 Zn01 O3 99.6(3) . . ?
C13 O6 Zn01 123.5(8) . . ?
C20 O8 Zn01 113.7(7) . . ?
C20 O8 H8' 99(10) . . ?
Zn01 O8 H8' 100(10) . . ?
C21 O9 H9 109.5 . . ?
C22 O10 H10 109.5 . . ?
C9 O3 Zn01 115.2(7) . . ?
C9 O3 H3' 107(5) . . ?
Zn01 O3 H3' 136(5) . . ?
C10 O4 H4 109.5 . . ?
C2 O1 Zn01 121.7(7) . . ?
C6 O2 H2 109.5 . . ?
C17 O7 H7 109.5 . . ?
H104 O104 H204 133(10) . . ?
H102 O102 H202 127(10) . . ?
H103 O103 H203 138(10) . . ?
C11 O5 H5' 109.5 . . ?
C18 N4 C19 120.6(9) . . ?
C18 N4 Zn01 124.7(7) . . ?
C19 N4 Zn01 114.7(7) . . ?
H101 O101 H201 102(9) . . ?
C1 N1 C5 118.7(11) . . ?
C7 N2 C8 120.9(8) . . ?
C7 N2 Zn01 124.3(8) . . ?
C8 N2 Zn01 114.7(7) . . ?
H200 O100 H100 131(10) . . ?
C16 N3 C12 121.0(11) . . ?
N1 C1 C2 122.8(10) . . ?
N1 C1 C011 118.0(12) . . ?
C2 C1 C011 119.2(13) . . ?
O6 C13 C14 125.0(11) . . ?
O6 C13 C12 117.6(10) . . ?
C14 C13 C12 117.5(11) . . ?
O10 C22 C19 114.5(8) . . ?
O10 C22 H22A 108.6 . . ?
C19 C22 H22A 108.6 . . ?
O10 C22 H22B 108.6 . . ?
C19 C22 H22B 108.6 . . ?
H22A C22 H22B 107.6 . . ?
N4 C19 C20 105.7(8) . . ?
N4 C19 C21 106.5(8) . . ?
C20 C19 C21 110.1(10) . . ?
N4 C19 C22 116.9(11) . . ?
C20 C19 C22 108.6(8) . . ?
C21 C19 C22 108.9(8) . . ?
C15 C14 C13 119.4(11) . . ?
C15 C14 C18 119.7(10) . . ?
C13 C14 C18 120.9(11) . . ?
N4 C18 C14 125.3(9) . . ?
N4 C18 H18' 121(6) . . ?
C14 C18 H18' 113(6) . . ?
C16 C15 C14 118.6(10) . . ?
C16 C15 C17 118.6(11) . . ?
C14 C15 C17 122.7(11) . . ?
O3 C9 C8 109.1(8) . . ?
O3 C9 H9A 109.9 . . ?
C8 C9 H9A 109.9 . . ?
O3 C9 H9B 109.9 . . ?
C8 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
C2 C3 C4 118.1(12) . . ?
C2 C3 C7 124.0(12) . . ?
C4 C3 C7 117.9(9) . . ?
C5 C4 C3 117.9(10) . . ?
C5 C4 C6 118.4(11) . . ?
C3 C4 C6 123.6(11) . . ?
O7 C17 C15 114.3(9) . . ?
O7 C17 H17A 108.7 . . ?
C15 C17 H17A 108.7 . . ?
O7 C17 H17B 108.7 . . ?
C15 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
N1 C5 C4 124.0(12) . . ?
N1 C5 H5 118.0 . . ?
C4 C5 H5 118.0 . . ?
N3 C16 C15 122.9(12) . . ?
N3 C16 H16 118.5 . . ?
C15 C16 H16 118.5 . . ?
O4 C10 C8 112.6(10) . . ?
O4 C10 H10A 109.1 . . ?
C8 C10 H10A 109.1 . . ?
O4 C10 H10B 109.1 . . ?
C8 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
O1 C2 C3 123.3(12) . . ?
O1 C2 C1 118.3(10) . . ?
C3 C2 C1 118.4(12) . . ?
N2 C7 C3 124.1(9) . . ?
N2 C7 H7' 116(6) . . ?
C3 C7 H7' 120(6) . . ?
C1 C011 H01A 109.5 . . ?
C1 C011 H01B 109.5 . . ?
H01A C011 H01B 109.5 . . ?
C1 C011 H01C 109.5 . . ?
H01A C011 H01C 109.5 . . ?
H01B C011 H01C 109.5 . . ?
N2 C8 C9 106.5(7) . . ?
N2 C8 C11 116.6(11) . . ?
C9 C8 C11 109.5(8) . . ?
N2 C8 C10 104.5(8) . . ?
C9 C8 C10 111.1(10) . . ?
C11 C8 C10 108.5(8) . . ?
O2 C6 C4 115.0(10) . . ?
O2 C6 H6A 108.5 . . ?
C4 C6 H6A 108.5 . . ?
O2 C6 H6B 108.5 . . ?
C4 C6 H6B 108.5 . . ?
H6A C6 H6B 107.5 . . ?
O8 C20 C19 109.1(9) . . ?
O8 C20 H20A 109.9 . . ?
C19 C20 H20A 109.9 . . ?
O8 C20 H20B 109.9 . . ?
C19 C20 H20B 109.9 . . ?
H20A C20 H20B 108.3 . . ?
O5 C11 C8 112.9(8) . . ?
O5 C11 H11A 109.0 . . ?
C8 C11 H11A 109.0 . . ?
O5 C11 H11B 109.0 . . ?
C8 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C12 C016 H01D 109.5 . . ?
C12 C016 H01E 109.5 . . ?
H01D C016 H01E 109.5 . . ?
C12 C016 H01F 109.5 . . ?
H01D C016 H01F 109.5 . . ?
H01E C016 H01F 109.5 . . ?
O9 C21 C19 113.3(10) . . ?
O9 C21 H21A 108.9 . . ?
C19 C21 H21A 108.9 . . ?
O9 C21 H21B 108.9 . . ?
C19 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
N3 C12 C13 120.3(11) . . ?
N3 C12 C016 119.3(13) . . ?
C13 C12 C016 120.3(13) . . ?

_refine_diff_density_max         0.795
_refine_diff_density_min         -0.611
_refine_diff_density_rms         0.105


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol, Diethylether, Water'
####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2095332'
loop_
_audit_author_name
_audit_author_address
'Dr. Andrew G. Sykes'
;University of South Dakota
United States of America
;
_audit_update_record             
;
2021-07-08 deposited with the CCDC.	2021-09-27 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         'C12 H18 Cl Cu N2 O9, Cl O4'
_chemical_formula_sum            'C12 H18 Cl2 Cu N2 O13'
_chemical_formula_weight         532.72

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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                   5.877(2)
_cell_length_b                   9.125(4)
_cell_length_c                   18.214(8)
_cell_angle_alpha                86.630(17)
_cell_angle_beta                 80.725(15)
_cell_angle_gamma                74.305(14)
_cell_volume                     927.9(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3771
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      26.4

_exptl_crystal_description       Plate
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.907
_exptl_crystal_F_000             542
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    1.540
_shelx_estimated_absorpt_T_min   0.927
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24629
_diffrn_reflns_av_unetI/netI     0.1208
_diffrn_reflns_av_R_equivalents  0.2043
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.266
_diffrn_reflns_theta_max         26.417
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3771
_reflns_number_gt                2240
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_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)+(0.0981P)²+4.4804P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3771
_refine_ls_number_parameters     292
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1388
_refine_ls_R_factor_gt           0.0793
_refine_ls_wR_factor_ref         0.2299
_refine_ls_wR_factor_gt          0.1933
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_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
Cu1 Cu 0.94766(19) 0.34643(12) 0.73032(6) 0.0299(4) Uani 1 1 d . . . . .
Cl1 Cl 0.7166(4) 0.7708(2) 0.57478(12) 0.0346(6) Uani 1 1 d . . . . .
O4 O 0.2686(10) 0.2516(7) 0.7577(3) 0.0295(13) Uani 1 1 d D . . . .
O1 O 0.8952(10) 0.4922(6) 0.8047(3) 0.0294(13) Uani 1 1 d . . . . .
O3 O 0.9917(10) 0.1882(7) 0.6568(3) 0.0311(14) Uani 1 1 d D . . . .
O2 O 0.1702(11) 0.9151(6) 0.6925(3) 0.0348(14) Uani 1 1 d . . . . .
H2 H 0.277388 0.858159 0.664813 0.052 Uiso 1 1 calc R U . . .
O5 O 0.1663(10) 0.4580(7) 0.6363(3) 0.0309(14) Uani 1 1 d D . . . .
N2 N 0.6301(12) 0.4175(8) 0.7042(4) 0.0282(16) Uani 1 1 d . . . . .
N1 N 0.5215(14) 0.8190(8) 0.8951(5) 0.0335(18) Uani 1 1 d . . . . .
Cl2 Cl 0.6392(4) 0.2258(2) 0.90705(12) 0.0345(6) Uani 1 1 d . . . . .
O12 O 0.8213(11) 0.1627(7) 0.8451(3) 0.0379(15) Uani 1 1 d . . . . .
O8 O 0.8754(11) 0.6309(7) 0.5432(4) 0.0380(15) Uani 1 1 d . . . . .
O9 O 0.7611(12) 0.7871(8) 0.6481(4) 0.0444(17) Uani 1 1 d . . . . .
O13 O 0.7250(13) 0.3049(8) 0.9558(4) 0.0461(18) Uani 1 1 d . . . . .
O7 O 0.4729(11) 0.7567(8) 0.5794(4) 0.0424(17) Uani 1 1 d . . . . .
O10 O 0.4397(12) 0.3318(8) 0.8772(4) 0.0458(17) Uani 1 1 d . . . . .
O11 O 0.5557(15) 0.1052(8) 0.9470(4) 0.052(2) Uani 1 1 d . . . . .
O6 O 0.7464(13) 0.8957(7) 0.5280(4) 0.0475(17) Uani 1 1 d . . . . .
C10 C 0.8078(14) 0.2303(9) 0.6091(5) 0.0276(18) Uani 1 1 d . . . . .
H10A H 0.791959 0.140012 0.587027 0.033 Uiso 1 1 calc R U . . .
H10B H 0.851124 0.297619 0.569246 0.033 Uiso 1 1 calc R U . . .
C5 C 0.7004(16) 0.6951(10) 0.8815(5) 0.031(2) Uani 1 1 d . . . . .
C6 C 0.8835(16) 0.6505(11) 0.9323(5) 0.035(2) Uani 1 1 d . . . . .
H6A H 1.000302 0.558820 0.914874 0.053 Uiso 1 1 calc R U . . .
H6B H 0.960683 0.730524 0.933058 0.053 Uiso 1 1 calc R U . . .
H6C H 0.807581 0.633432 0.981546 0.053 Uiso 1 1 calc R U . . .
C9 C 0.5709(15) 0.3107(9) 0.6559(5) 0.0283(19) Uani 1 1 d . . . . .
C2 C 0.3196(15) 0.7773(10) 0.7991(5) 0.0305(19) Uani 1 1 d . . . . .
C3 C 0.5069(14) 0.6404(9) 0.7819(5) 0.0287(19) Uani 1 1 d . . . . .
C12 C 0.4037(14) 0.3915(10) 0.5994(5) 0.0303(19) Uani 1 1 d . . . . .
H12A H 0.467280 0.470408 0.572565 0.036 Uiso 1 1 calc R U . . .
H12B H 0.398790 0.318400 0.563480 0.036 Uiso 1 1 calc R U . . .
C8 C 0.4758(17) 0.5394(10) 0.7267(5) 0.031(2) Uani 1 1 d . . . . .
C1 C 0.3350(16) 0.8665(10) 0.8562(5) 0.034(2) Uani 1 1 d . . . . .
H1 H 0.219314 0.957468 0.867764 0.041 Uiso 1 1 calc R U . . .
C11 C 0.4793(14) 0.1906(10) 0.7047(5) 0.0299(19) Uani 1 1 d . . . . .
H11A H 0.443955 0.120684 0.672831 0.036 Uiso 1 1 calc R U . . .
H11B H 0.605494 0.132779 0.731459 0.036 Uiso 1 1 calc R U . . .
C7 C 0.1107(15) 0.8350(10) 0.7586(5) 0.034(2) Uani 1 1 d . . . . .
H7A H 0.055288 0.749816 0.746220 0.040 Uiso 1 1 calc R U . . .
H7B H -0.018773 0.901858 0.790682 0.040 Uiso 1 1 calc R U . . .
C4 C 0.7075(16) 0.6022(10) 0.8199(5) 0.034(2) Uani 1 1 d . . . . .
H8 H 0.332(17) 0.574(10) 0.713(5) 0.03(2) Uiso 1 1 d . . . . .
H4 H 0.33(2) 0.269(17) 0.798(5) 0.10(5) Uiso 1 1 d D . . . .
H5 H 0.066(16) 0.519(10) 0.608(5) 0.06(3) Uiso 1 1 d D . . . .
H3 H 1.08(3) 0.094(9) 0.668(11) 0.18(9) Uiso 1 1 d D . . . .
H1' H 0.526(15) 0.867(10) 0.931(5) 0.02(2) Uiso 1 1 d . . . . .


_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
Cu1 O1 1.885(5) . ?
Cu1 N2 1.930(7) . ?
Cu1 O3 1.965(6) . ?
Cu1 O4 1.981(6) 1_655 ?
Cu1 O5 2.327(6) 1_655 ?
Cl1 O6 1.415(7) . ?
Cl1 O9 1.425(7) . ?
Cl1 O8 1.449(6) . ?
Cl1 O7 1.461(7) . ?
O4 C11 1.443(10) . ?
O4 H4 0.90(2) . ?
O1 C4 1.280(10) . ?
O3 C10 1.452(10) . ?
O3 H3 0.90(2) . ?
O2 C7 1.416(11) . ?
O2 H2 0.8200 . ?
O5 C12 1.434(10) . ?
O5 H5 0.90(2) . ?
N2 C8 1.271(11) . ?
N2 C9 1.494(10) . ?
N1 C5 1.324(11) . ?
N1 C1 1.359(12) . ?
N1 H1' 0.81(9) . ?
Cl2 O13 1.408(6) . ?
Cl2 O11 1.436(7) . ?
Cl2 O12 1.450(6) . ?
Cl2 O10 1.462(7) . ?
C10 C9 1.531(11) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C5 C4 1.433(11) . ?
C5 C6 1.489(12) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C9 C11 1.526(12) . ?
C9 C12 1.554(12) . ?
C2 C1 1.386(11) . ?
C2 C3 1.436(12) . ?
C2 C7 1.492(12) . ?
C3 C4 1.416(12) . ?
C3 C8 1.466(11) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C8 H8 0.89(9) . ?
C1 H1 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 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
O1 Cu1 N2 94.7(3) . . ?
O1 Cu1 O3 176.8(3) . . ?
N2 Cu1 O3 84.5(3) . . ?
O1 Cu1 O4 89.2(2) . 1_655 ?
N2 Cu1 O4 174.0(3) . 1_655 ?
O3 Cu1 O4 91.3(2) . 1_655 ?
O1 Cu1 O5 98.8(2) . 1_655 ?
N2 Cu1 O5 101.4(3) . 1_655 ?
O3 Cu1 O5 84.4(2) . 1_655 ?
O4 Cu1 O5 82.5(2) 1_655 1_655 ?
O6 Cl1 O9 111.8(4) . . ?
O6 Cl1 O8 109.8(4) . . ?
O9 Cl1 O8 109.7(4) . . ?
O6 Cl1 O7 109.9(4) . . ?
O9 Cl1 O7 108.6(4) . . ?
O8 Cl1 O7 106.9(4) . . ?
C11 O4 Cu1 124.0(5) . 1_455 ?
C11 O4 H4 103(10) . . ?
Cu1 O4 H4 128(10) 1_455 . ?
C4 O1 Cu1 126.0(6) . . ?
C10 O3 Cu1 110.9(5) . . ?
C10 O3 H3 127(10) . . ?
Cu1 O3 H3 117(10) . . ?
C7 O2 H2 109.5 . . ?
C12 O5 Cu1 126.8(5) . 1_455 ?
C12 O5 H5 116(7) . . ?
Cu1 O5 H5 109(7) 1_455 . ?
C8 N2 C9 120.8(7) . . ?
C8 N2 Cu1 125.6(6) . . ?
C9 N2 Cu1 113.5(5) . . ?
C5 N1 C1 125.5(8) . . ?
C5 N1 H1' 115(6) . . ?
C1 N1 H1' 120(6) . . ?
O13 Cl2 O11 109.6(4) . . ?
O13 Cl2 O12 112.0(4) . . ?
O11 Cl2 O12 109.4(4) . . ?
O13 Cl2 O10 108.6(4) . . ?
O11 Cl2 O10 109.0(5) . . ?
O12 Cl2 O10 108.2(4) . . ?
O3 C10 C9 108.8(6) . . ?
O3 C10 H10A 109.9 . . ?
C9 C10 H10A 109.9 . . ?
O3 C10 H10B 109.9 . . ?
C9 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
N1 C5 C4 119.0(8) . . ?
N1 C5 C6 119.7(8) . . ?
C4 C5 C6 121.2(8) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C9 C11 109.2(7) . . ?
N2 C9 C10 105.7(6) . . ?
C11 C9 C10 108.0(7) . . ?
N2 C9 C12 113.8(7) . . ?
C11 C9 C12 113.8(7) . . ?
C10 C9 C12 105.8(7) . . ?
C1 C2 C3 118.3(8) . . ?
C1 C2 C7 116.7(8) . . ?
C3 C2 C7 125.0(7) . . ?
C4 C3 C2 120.5(7) . . ?
C4 C3 C8 121.9(8) . . ?
C2 C3 C8 117.6(8) . . ?
O5 C12 C9 111.1(7) . . ?
O5 C12 H12A 109.4 . . ?
C9 C12 H12A 109.4 . . ?
O5 C12 H12B 109.4 . . ?
C9 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
N2 C8 C3 124.4(9) . . ?
N2 C8 H8 126(6) . . ?
C3 C8 H8 110(6) . . ?
N1 C1 C2 119.1(8) . . ?
N1 C1 H1 120.5 . . ?
C2 C1 H1 120.5 . . ?
O4 C11 C9 114.3(7) . . ?
O4 C11 H11A 108.7 . . ?
C9 C11 H11A 108.7 . . ?
O4 C11 H11B 108.7 . . ?
C9 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
O2 C7 C2 111.6(7) . . ?
O2 C7 H7A 109.3 . . ?
C2 C7 H7A 109.3 . . ?
O2 C7 H7B 109.3 . . ?
C2 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
O1 C4 C3 126.2(8) . . ?
O1 C4 C5 116.6(8) . . ?
C3 C4 C5 117.2(8) . . ?

_refine_diff_density_max         0.773
_refine_diff_density_min         -0.902
_refine_diff_density_rms         0.163


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile, Diethylether'
