# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_zj
_audit_block_doi                 10.5517/ccdc.csd.cc25qjct
_database_code_depnum_ccdc_archive 'CCDC 2017646'
loop_
_audit_author_name
_audit_author_address
XY
;Liaoning Normal University
China
;
_audit_update_record             
;
2020-07-20 deposited with the CCDC.	2020-12-28 downloaded from the CCDC.
;
_audit_creation_date             2020-07-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C13 H9 Co N2 O4, 2(H2 O)'
_chemical_formula_sum            'C13 H15 Co N2 O6'
_chemical_formula_weight         354.20
_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'
Co Co 0.3494 0.9721 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.6083(16)
_cell_length_b                   7.6426(9)
_cell_length_c                   16.1273(19)
_cell_angle_alpha                90
_cell_angle_beta                 109.076(2)
_cell_angle_gamma                90
_cell_volume                     1468.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4337
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      30.941
_cell_measurement_theta_min      3.167
_shelx_estimated_absorpt_T_max   0.679
_shelx_estimated_absorpt_T_min   0.574
_exptl_absorpt_coefficient_mu    1.199
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6165
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1200 before and 0.0519 after correction.
The Ratio of minimum to maximum transmission is 0.8262.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.35
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6635
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        24.993
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         1.709
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_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                2252
_reflns_number_total             2555
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         3.047
_refine_diff_density_min         -1.506
_refine_diff_density_rms         0.165
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2555
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0844
_refine_ls_restrained_S_all      1.061
_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)+(0.1741P)²+5.2509P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2520
_refine_ls_wR_factor_ref         0.2571
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Riding coordinates:
 O2W(H2WA,H2WB)
2.b Free rotating group:
 O1W(H1WA,H1WB)
2.c Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B)
2.d Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C8(H8), C12(H12), C10(H10), C9(H9), C13(H13)
;
_atom_sites_solution_hydrogens   mixed
_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
Co1 Co 0.18614(7) 0.49346(8) 0.31755(4) 0.0300(4) Uani 1 1 d . . . . .
C4 C 0.0741(5) 0.2389(7) 0.4000(4) 0.0299(12) Uani 1 1 d . . . . .
N1 N 0.0437(4) 0.3771(6) 0.3364(3) 0.0353(11) Uani 1 1 d . . . . .
H1A H 0.005336 0.458368 0.354115 0.042 Uiso 1 1 calc R . . . .
H1B H -0.000655 0.334455 0.285519 0.042 Uiso 1 1 calc R . . . .
C2 C 0.1386(5) -0.0564(7) 0.4356(4) 0.0315(12) Uani 1 1 d . . . . .
C5 C 0.0857(5) 0.2703(7) 0.4881(4) 0.0317(12) Uani 1 1 d . . . . .
H5 H 0.068103 0.379411 0.505534 0.038 Uiso 1 1 calc R . . . .
C3 C 0.0992(5) 0.0762(7) 0.3743(4) 0.0328(12) Uani 1 1 d . . . . .
H3 H 0.089728 0.055087 0.315495 0.039 Uiso 1 1 calc R . . . .
C6 C 0.1235(4) 0.1381(7) 0.5487(3) 0.0305(12) Uani 1 1 d . . . . .
C8 C 0.1514(5) -0.0243(8) 0.5232(4) 0.0346(13) Uani 1 1 d . . . . .
H8 H 0.178659 -0.111761 0.564774 0.042 Uiso 1 1 calc R . . . .
N2 N 0.3139(4) 0.3316(7) 0.3853(3) 0.0396(12) Uani 1 1 d . . . . .
C11 C 0.4621(6) 0.0680(10) 0.4763(5) 0.0457(15) Uani 1 1 d . . . . .
C12 C 0.4042(8) 0.0566(13) 0.3885(5) 0.074(3) Uani 1 1 d . . . . .
H12 H 0.413103 -0.041760 0.357455 0.088 Uiso 1 1 calc R . . . .
C10 C 0.4381(9) 0.2148(13) 0.5182(6) 0.086(3) Uani 1 1 d . . . . .
H10 H 0.471378 0.227677 0.578512 0.103 Uiso 1 1 calc R . . . .
C9 C 0.3655(8) 0.3406(12) 0.4710(5) 0.076(3) Uani 1 1 d . . . . .
H9 H 0.351888 0.437456 0.500904 0.091 Uiso 1 1 calc R . . . .
C13 C 0.3329(7) 0.1887(12) 0.3453(5) 0.069(2) Uani 1 1 d . . . . .
H13 H 0.296339 0.177131 0.285305 0.083 Uiso 1 1 calc R . . . .
C1A C 0.1656(5) -0.2314(8) 0.4075(4) 0.0369(13) Uani 1 1 d . . . . .
O1 O 0.1482(4) -0.2567(5) 0.3261(3) 0.0465(11) Uani 1 1 d . . . . .
O2 O 0.2034(5) -0.3485(6) 0.4616(3) 0.0594(14) Uani 1 1 d . . . . .
C7 C 0.1339(5) 0.1704(8) 0.6438(4) 0.0324(12) Uani 1 1 d . . . . .
O3 O 0.1695(4) 0.0401(7) 0.6946(3) 0.0477(11) Uani 1 1 d . . . . .
O4 O 0.1099(4) 0.3138(7) 0.6662(3) 0.0526(12) Uani 1 1 d . . . . .
O2W O 0.508(3) -0.030(6) 0.2213(17) 0.63(4) Uani 1 1 d . . . . .
H2WA H 0.575367 -0.048014 0.254127 0.951 Uiso 1 1 d R . . . .
H2WB H 0.502737 -0.051954 0.168297 0.951 Uiso 1 1 d R . . . .
O1W O 0.7365(9) 0.0818(14) 0.8559(7) 0.119(3) Uiso 1 1 d . . . . .
H1WA H 0.688666 0.031662 0.874683 0.179 Uiso 1 1 d G . . . .
H1WB H 0.787282 0.005318 0.861363 0.179 Uiso 1 1 d G . . . .


_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
Co1 N1 2.113(5) . ?
Co1 N2 2.041(5) . ?
Co1 O1 1.984(4) 1_565 ?
Co1 O3 1.942(5) 4_565 ?
C4 N1 1.435(7) . ?
C4 C5 1.400(8) . ?
C4 C3 1.381(8) . ?
C2 C3 1.390(9) . ?
C2 C8 1.389(9) . ?
C2 C1A 1.487(8) . ?
C5 C6 1.377(8) . ?
C6 C8 1.389(8) . ?
C6 C7 1.516(7) . ?
N2 C9 1.323(9) . ?
N2 C13 1.329(9) . ?
C11 C11 1.450(14) 3_656 ?
C11 C12 1.367(11) . ?
C11 C10 1.393(11) . ?
C12 C13 1.380(11) . ?
C10 C9 1.373(11) . ?
C1A O1 1.273(7) . ?
C1A O2 1.232(8) . ?
C7 O3 1.275(7) . ?
C7 O4 1.223(7) . ?

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
N2 Co1 N1 103.1(2) . . ?
O1 Co1 N1 99.17(19) 1_565 . ?
O1 Co1 N2 135.4(2) 1_565 . ?
O3 Co1 N1 106.1(2) 4_565 . ?
O3 Co1 N2 105.6(2) 4_565 . ?
O3 Co1 O1 104.5(2) 4_565 1_565 ?
C5 C4 N1 121.0(5) . . ?
C3 C4 N1 118.8(5) . . ?
C3 C4 C5 120.1(5) . . ?
C4 N1 Co1 111.9(4) . . ?
C3 C2 C1A 120.2(5) . . ?
C8 C2 C3 119.4(5) . . ?
C8 C2 C1A 120.5(5) . . ?
C6 C5 C4 119.4(5) . . ?
C4 C3 C2 120.5(5) . . ?
C5 C6 C8 120.5(5) . . ?
C5 C6 C7 119.6(5) . . ?
C8 C6 C7 119.9(5) . . ?
C6 C8 C2 120.2(6) . . ?
C9 N2 Co1 124.1(5) . . ?
C9 N2 C13 116.4(6) . . ?
C13 N2 Co1 118.3(5) . . ?
C12 C11 C11 122.5(9) . 3_656 ?
C12 C11 C10 115.3(7) . . ?
C10 C11 C11 122.1(8) . 3_656 ?
C11 C12 C13 121.0(8) . . ?
C9 C10 C11 120.4(7) . . ?
N2 C9 C10 123.7(7) . . ?
N2 C13 C12 123.2(7) . . ?
O1 C1A C2 118.1(5) . . ?
O2 C1A C2 120.7(5) . . ?
O2 C1A O1 121.1(5) . . ?
C1A O1 Co1 104.7(4) . 1_545 ?
O3 C7 C6 114.8(5) . . ?
O4 C7 C6 119.9(5) . . ?
O4 C7 O3 125.4(5) . . ?
C7 O3 Co1 131.1(4) . 4_566 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1W H1WA O2 0.85 2.70 2.840(12) 90.3 2_656 yes
O1W H1WA O2W 0.85 2.46 2.95(4) 117.8 3_656 yes

_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_zj_sq
_audit_block_doi                 10.5517/ccdc.csd.cc25qjhy
_database_code_depnum_ccdc_archive 'CCDC 2017650'
loop_
_audit_author_name
_audit_author_address
XY 'Liaoning Normal University'
_audit_update_record             
;
2020-07-20 deposited with the CCDC.	2020-12-28 downloaded from the CCDC.
;
_audit_creation_date             2020-07-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H9 Cu N2 O4'
_chemical_formula_sum            'C13 H9 Cu N2 O4'
_chemical_formula_weight         320.76
_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'
Cu Cu 0.3201 1.2651 '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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.5486(14)
_cell_length_b                   7.6374(9)
_cell_length_c                   16.0778(18)
_cell_angle_alpha                90
_cell_angle_beta                 109.037(2)
_cell_angle_gamma                90
_cell_volume                     1456.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3955
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      29.338
_cell_measurement_theta_min      3.172
_shelx_estimated_absorpt_T_max   0.612
_shelx_estimated_absorpt_T_min   0.485
_exptl_absorpt_coefficient_mu    1.512
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.5715
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0570 before and 0.0300 after correction.
The Ratio of minimum to maximum transmission is 0.7662.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.36
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7230
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.717
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_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                2297
_reflns_number_total             2557
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2557
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0373
_refine_ls_restrained_S_all      1.158
_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)+(0.0195P)²+2.7098P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0843
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C3(H3), C12(H12), C10(H10), C9(H9), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Cu1 Cu 0.31044(4) 0.50195(5) 0.18182(2) 0.03295(14) Uani 1 1 d . . . . .
N2 N 0.4537(2) 0.6205(3) 0.16392(16) 0.0333(6) Uani 1 1 d . . . . .
H2A H 0.497349 0.663838 0.215072 0.040 Uiso 1 1 calc R . . . .
H2B H 0.493150 0.539554 0.146816 0.040 Uiso 1 1 calc R . . . .
C2 C 0.3619(3) 1.0530(4) 0.06450(19) 0.0279(7) Uani 1 1 d . . . . .
C7 C 0.4240(3) 0.7582(4) 0.09991(18) 0.0271(6) Uani 1 1 d . . . . .
C6 C 0.4125(3) 0.7265(4) 0.01316(19) 0.0292(7) Uani 1 1 d . . . . .
H6 H 0.429692 0.616654 -0.003968 0.035 Uiso 1 1 calc R . . . .
N1AA N 0.1847(2) 0.6678(3) 0.11485(17) 0.0336(6) Uani 1 1 d . . . . .
C8 C 0.3993(3) 0.9209(4) 0.12567(18) 0.0272(6) Uani 1 1 d . . . . .
H8 H 0.407924 0.941868 0.184483 0.033 Uiso 1 1 calc R . . . .
C4 C 0.3754(3) 0.8584(4) -0.04853(18) 0.0274(7) Uani 1 1 d . . . . .
C3 C 0.3496(3) 1.0223(4) -0.02290(19) 0.0307(7) Uani 1 1 d . . . . .
H3 H 0.324138 1.110968 -0.064314 0.037 Uiso 1 1 calc R . . . .
C11 C 0.0379(3) 0.9297(5) 0.0243(2) 0.0391(8) Uani 1 1 d . . . . .
C12 C 0.0944(4) 0.9410(6) 0.1119(3) 0.0651(13) Uani 1 1 d . . . . .
H12 H 0.084597 1.038527 0.143313 0.078 Uiso 1 1 calc R . . . .
C10 C 0.0608(5) 0.7846(6) -0.0166(3) 0.0819(18) Uani 1 1 d . . . . .
H10 H 0.026352 0.770954 -0.076913 0.098 Uiso 1 1 calc R . . . .
C9 C 0.1336(4) 0.6593(6) 0.0300(3) 0.0689(14) Uani 1 1 d . . . . .
H9 H 0.147599 0.562900 -0.000223 0.083 Uiso 1 1 calc R . . . .
C13 C 0.1655(4) 0.8097(6) 0.1541(2) 0.0635(13) Uani 1 1 d . . . . .
H13 H 0.202559 0.821434 0.214185 0.076 Uiso 1 1 calc R . . . .
C1 C 0.3343(3) 1.2291(4) 0.0925(2) 0.0328(7) Uani 1 1 d . . . . .
O3 O 0.3546(2) 1.2555(3) 0.17427(15) 0.0424(6) Uani 1 1 d . . . . .
O4 O 0.2946(3) 1.3441(3) 0.03756(17) 0.0575(8) Uani 1 1 d . . . . .
C5 C 0.3651(3) 0.8266(4) -0.1435(2) 0.0328(7) Uani 1 1 d . . . . .
O2 O 0.3309(2) 0.9550(3) -0.19414(14) 0.0479(7) Uani 1 1 d . . . . .
O0AA O 0.3879(2) 0.6792(3) -0.16609(15) 0.0499(7) Uani 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 N2 2.114(3) . ?
Cu1 N1AA 2.036(3) . ?
Cu1 O3 1.977(2) 1_545 ?
Cu1 O2 1.954(2) 4_576 ?
N2 C7 1.433(4) . ?
C2 C8 1.380(4) . ?
C2 C3 1.383(4) . ?
C2 C1 1.494(4) . ?
C7 C6 1.376(4) . ?
C7 C8 1.377(4) . ?
C6 C4 1.384(4) . ?
N1AA C9 1.305(4) . ?
N1AA C13 1.315(5) . ?
C4 C3 1.389(4) . ?
C4 C5 1.510(4) . ?
C11 C11 1.478(6) 3_575 ?
C11 C12 1.357(5) . ?
C11 C10 1.366(5) . ?
C12 C13 1.367(5) . ?
C10 C9 1.366(5) . ?
C1 O3 1.271(4) . ?
C1 O4 1.230(4) . ?
C5 O2 1.257(4) . ?
C5 O0AA 1.245(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1AA Cu1 N2 102.03(10) . . ?
O3 Cu1 N2 97.57(10) 1_545 . ?
O3 Cu1 N1AA 138.09(11) 1_545 . ?
O2 Cu1 N2 103.43(11) 4_576 . ?
O2 Cu1 N1AA 104.86(11) 4_576 . ?
O2 Cu1 O3 106.05(10) 4_576 1_545 ?
C7 N2 Cu1 112.3(2) . . ?
C8 C2 C3 120.0(3) . . ?
C8 C2 C1 120.1(3) . . ?
C3 C2 C1 119.9(3) . . ?
C6 C7 N2 121.0(3) . . ?
C6 C7 C8 120.3(3) . . ?
C8 C7 N2 118.5(3) . . ?
C7 C6 C4 119.9(3) . . ?
C9 N1AA Cu1 123.6(2) . . ?
C9 N1AA C13 116.0(3) . . ?
C13 N1AA Cu1 119.4(2) . . ?
C7 C8 C2 120.2(3) . . ?
C6 C4 C3 120.0(3) . . ?
C6 C4 C5 120.4(3) . . ?
C3 C4 C5 119.6(3) . . ?
C2 C3 C4 119.7(3) . . ?
C12 C11 C11 122.0(4) . 3_575 ?
C12 C11 C10 115.5(3) . . ?
C10 C11 C11 122.3(4) . 3_575 ?
C11 C12 C13 120.2(4) . . ?
C11 C10 C9 120.8(4) . . ?
N1AA C9 C10 123.4(4) . . ?
N1AA C13 C12 124.0(3) . . ?
O3 C1 C2 117.8(3) . . ?
O4 C1 C2 120.4(3) . . ?
O4 C1 O3 121.8(3) . . ?
C1 O3 Cu1 104.41(19) . 1_565 ?
O2 C5 C4 115.3(3) . . ?
O0AA C5 C4 119.2(3) . . ?
O0AA C5 O2 125.4(3) . . ?
C5 O2 Cu1 134.1(2) . 4_575 ?

_platon_squeeze_details          ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 -0.040 0.250 204 45 ' '
2 0.000 -0.008 0.750 204 45 ' '

_platon_squeeze_void_probe_radius 1.20
_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_zj_CCDC1
_audit_block_doi                 10.5517/ccdc.csd.cc25qjn3
_database_code_depnum_ccdc_archive 'CCDC 2017655'
loop_
_audit_author_name
_audit_author_address
XY 'Liaoning Normal University'
_audit_update_record             
;
2020-07-20 deposited with the CCDC.	2020-12-28 downloaded from the CCDC.
;
_audit_creation_date             2020-07-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(H2 O0.5), C13 H9 N2 O4 Zn'
_chemical_formula_sum            'C13 H13 N2 O6 Zn'
_chemical_formula_weight         358.62
_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'
Zn Zn 0.2839 1.4301 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.3235(9)
_cell_length_b                   7.6722(5)
_cell_length_c                   16.1144(12)
_cell_angle_alpha                90
_cell_angle_beta                 108.5810(10)
_cell_angle_gamma                90
_cell_volume                     1444.17(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3642
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      29.561
_cell_measurement_theta_min      2.682
_shelx_estimated_absorpt_T_max   0.537
_shelx_estimated_absorpt_T_min   0.472
_exptl_absorpt_coefficient_mu    1.732
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6539
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0385 before and 0.0315 after correction.
The Ratio of minimum to maximum transmission is 0.8767.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             732
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.41
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9382
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.599
_diffrn_reflns_theta_min         1.743
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_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                3003
_reflns_number_total             3882
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         1.322
_refine_diff_density_min         -0.874
_refine_diff_density_rms         0.132
_refine_ls_extinction_coef       0.0046(13)
_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   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3882
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0532
_refine_ls_restrained_S_all      1.114
_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)+(0.0956P)²+2.7798P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1731
_refine_ls_wR_factor_ref         0.1856
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Others
 Fixed Sof: O2W(0.5) O1W(0.5)
3.a Riding coordinates:
 O2W(H2WA,H2WB), O1W(H1WA,H1WB)
3.b Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B)
3.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C15(H15), C17(H17), C18(H18), C20(H20), C19(H19)
;
_atom_sites_solution_hydrogens   mixed
_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
O2W O 0.1308(13) 0.3418(13) 0.2175(7) 0.164(8) Uani 0.5 1 d . . P . .
H2WA H 0.076455 0.414854 0.208300 0.247 Uiso 1 1 d R . . . .
H2WB H 0.151825 0.310224 0.270850 0.247 Uiso 1 1 d R . . . .
O1W O 0.7672(6) 0.5846(8) 0.1443(4) 0.0534(18) Uani 0.5 1 d . . P . .
H1WA H 0.799822 0.485631 0.149772 0.080 Uiso 1 1 d R . . . .
H1WB H 0.760122 0.625741 0.093832 0.080 Uiso 1 1 d R . . . .
Zn1 Zn 0.31227(4) 0.50462(5) 0.18476(2) 0.03293(19) Uani 1 1 d . . . . .
N2 N 0.4575(3) 0.6226(4) 0.16413(18) 0.0290(6) Uani 1 1 d . . . . .
H2A H 0.502780 0.665813 0.214518 0.035 Uiso 1 1 calc R . . . .
H2B H 0.496888 0.542131 0.146022 0.035 Uiso 1 1 calc R . . . .
C2 C 0.3587(3) 1.0541(4) 0.0659(2) 0.0247(7) Uani 1 1 d . . . . .
C5 C 0.4249(3) 0.7597(4) 0.1004(2) 0.0240(6) Uani 1 1 d . . . . .
N1 N 0.1814(3) 0.6640(4) 0.1166(2) 0.0340(7) Uani 1 1 d . . . . .
C7 C 0.4131(3) 0.7300(4) 0.0131(2) 0.0260(7) Uani 1 1 d . . . . .
H7 H 0.431142 0.621394 -0.004484 0.031 Uiso 1 1 calc R . . . .
C8 C 0.3978(3) 0.9219(4) 0.1266(2) 0.0262(7) Uani 1 1 d . . . . .
H8 H 0.406075 0.941804 0.185236 0.031 Uiso 1 1 calc R . . . .
C10 C 0.3744(3) 0.8619(4) -0.0479(2) 0.0245(7) Uani 1 1 d . . . . .
C13 C 0.3309(3) 1.2304(4) 0.0940(2) 0.0292(7) Uani 1 1 d . . . . .
C15 C 0.3458(3) 1.0241(4) -0.0223(2) 0.0258(7) Uani 1 1 d . . . . .
H15 H 0.318355 1.111772 -0.063466 0.031 Uiso 1 1 calc R . . . .
C16 C 0.0367(4) 0.9282(5) 0.0245(3) 0.0359(8) Uani 1 1 d . . . . .
C17 C 0.0619(6) 0.7833(7) -0.0170(3) 0.0700(19) Uani 1 1 d . . . . .
H17 H 0.030490 0.772572 -0.077486 0.084 Uiso 1 1 calc R . . . .
C18 C 0.1326(5) 0.6554(7) 0.0299(3) 0.0605(15) Uani 1 1 d . . . . .
H18 H 0.147243 0.558796 0.000292 0.073 Uiso 1 1 calc R . . . .
C20 C 0.1594(5) 0.8032(7) 0.1564(3) 0.0592(15) Uani 1 1 d . . . . .
H20 H 0.191870 0.810420 0.216926 0.071 Uiso 1 1 calc R . . . .
C19 C 0.0905(5) 0.9397(8) 0.1131(3) 0.0619(16) Uani 1 1 d . . . . .
H19 H 0.080970 1.037997 0.143801 0.074 Uiso 1 1 calc R . . . .
O4 O 0.3479(3) 1.2552(3) 0.17534(17) 0.0365(6) Uani 1 1 d . . . . .
O3 O 0.2945(3) 1.3477(4) 0.0398(2) 0.0530(9) Uani 1 1 d . . . . .
C11 C 0.3631(3) 0.8312(5) -0.1430(2) 0.0282(7) Uani 1 1 d . . . . .
O2 O 0.3266(3) 0.9604(4) -0.19313(17) 0.0403(7) Uani 1 1 d . . . . .
O1 O 0.3887(3) 0.6881(4) -0.16636(18) 0.0436(7) Uani 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
Zn1 N2 2.124(3) . ?
Zn1 N1 2.043(3) . ?
Zn1 O4 1.980(3) 1_545 ?
Zn1 O2 1.937(3) 4_576 ?
N2 C5 1.436(4) . ?
C2 C8 1.385(5) . ?
C2 C13 1.500(5) . ?
C2 C15 1.398(5) . ?
C5 C7 1.385(4) . ?
C5 C8 1.389(4) . ?
N1 C18 1.334(5) . ?
N1 C20 1.318(5) . ?
C7 C10 1.386(5) . ?
C10 C15 1.391(5) . ?
C10 C11 1.513(4) . ?
C13 O4 1.274(4) . ?
C13 O3 1.235(5) . ?
C16 C16 1.483(8) 3_575 ?
C16 C17 1.384(6) . ?
C16 C19 1.372(6) . ?
C17 C18 1.369(6) . ?
C20 C19 1.388(6) . ?
C11 O2 1.267(5) . ?
C11 O1 1.234(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Zn1 N2 102.75(13) . . ?
O4 Zn1 N2 100.45(12) 1_545 . ?
O4 Zn1 N1 133.91(13) 1_545 . ?
O2 Zn1 N2 106.92(13) 4_576 . ?
O2 Zn1 N1 105.34(13) 4_576 . ?
O2 Zn1 O4 105.12(12) 4_576 1_545 ?
C5 N2 Zn1 111.5(2) . . ?
C8 C2 C13 120.6(3) . . ?
C8 C2 C15 119.9(3) . . ?
C15 C2 C13 119.6(3) . . ?
C7 C5 N2 121.4(3) . . ?
C7 C5 C8 119.9(3) . . ?
C8 C5 N2 118.6(3) . . ?
C18 N1 Zn1 123.3(3) . . ?
C20 N1 Zn1 118.2(3) . . ?
C20 N1 C18 117.1(4) . . ?
C5 C7 C10 120.1(3) . . ?
C2 C8 C5 120.3(3) . . ?
C7 C10 C15 120.3(3) . . ?
C7 C10 C11 120.4(3) . . ?
C15 C10 C11 119.3(3) . . ?
O4 C13 C2 117.9(3) . . ?
O3 C13 C2 120.6(3) . . ?
O3 C13 O4 121.5(3) . . ?
C10 C15 C2 119.5(3) . . ?
C17 C16 C16 122.2(5) . 3_575 ?
C19 C16 C16 121.1(5) . 3_575 ?
C19 C16 C17 116.5(4) . . ?
C18 C17 C16 120.7(4) . . ?
N1 C18 C17 122.6(4) . . ?
N1 C20 C19 123.6(4) . . ?
C16 C19 C20 119.4(4) . . ?
C13 O4 Zn1 104.8(2) . 1_565 ?
O2 C11 C10 115.1(3) . . ?
O1 C11 C10 119.8(3) . . ?
O1 C11 O2 125.1(3) . . ?
C11 O2 Zn1 130.9(3) . 4_575 ?

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
Zn1 N2 C5 C7 -95.5(3) . . . . ?
Zn1 N2 C5 C8 80.3(3) . . . . ?
Zn1 N1 C18 C17 -166.5(6) . . . . ?
Zn1 N1 C20 C19 165.9(5) . . . . ?
N2 C5 C7 C10 175.8(3) . . . . ?
N2 C5 C8 C2 -175.7(3) . . . . ?
C2 C13 O4 Zn1 175.9(3) . . . 1_565 ?
C5 C7 C10 C15 -0.8(5) . . . . ?
C5 C7 C10 C11 179.0(3) . . . . ?
N1 C20 C19 C16 3.5(10) . . . . ?
C7 C5 C8 C2 0.2(5) . . . . ?
C7 C10 C15 C2 1.3(5) . . . . ?
C7 C10 C11 O2 179.8(3) . . . . ?
C7 C10 C11 O1 -0.2(5) . . . . ?
C8 C2 C13 O4 2.1(5) . . . . ?
C8 C2 C13 O3 -179.0(4) . . . . ?
C8 C2 C15 C10 -1.1(5) . . . . ?
C8 C5 C7 C10 0.0(5) . . . . ?
C10 C11 O2 Zn1 172.9(3) . . . 4_575 ?
C13 C2 C8 C5 -179.1(3) . . . . ?
C13 C2 C15 C10 178.3(3) . . . . ?
C15 C2 C8 C5 0.3(6) . . . . ?
C15 C2 C13 O4 -177.3(3) . . . . ?
C15 C2 C13 O3 1.6(6) . . . . ?
C15 C10 C11 O2 -0.3(5) . . . . ?
C15 C10 C11 O1 179.7(4) . . . . ?
C16 C16 C17 C18 178.1(7) 3_575 . . . ?
C16 C16 C19 C20 -179.4(6) 3_575 . . . ?
C16 C17 C18 N1 -0.8(11) . . . . ?
C17 C16 C19 C20 -4.4(9) . . . . ?
C18 N1 C20 C19 -1.0(9) . . . . ?
C20 N1 C18 C17 -0.4(10) . . . . ?
C19 C16 C17 C18 3.2(10) . . . . ?
O3 C13 O4 Zn1 -3.0(5) . . . 1_565 ?
C11 C10 C15 C2 -178.5(3) . . . . ?
O1 C11 O2 Zn1 -7.1(6) . . . 4_575 ?

_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_zj_CCDC2
_audit_block_doi                 10.5517/ccdc.csd.cc25qjgx
_database_code_depnum_ccdc_archive 'CCDC 2017649'
loop_
_audit_author_name
_audit_author_address
XY 'Liaoning Normal University'
_audit_update_record             
;
2020-07-20 deposited with the CCDC.	2020-12-28 downloaded from the CCDC.
;
_audit_creation_date             2020-07-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C13 H9 Cr N2 O4, 2(H2 O)'
_chemical_formula_sum            'C13 H13 Cr N2 O6'
_chemical_formula_weight         345.25
_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'
Cr Cr 0.3209 0.6236 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.5435(9)
_cell_length_b                   7.6671(6)
_cell_length_c                   16.1534(11)
_cell_angle_alpha                90
_cell_angle_beta                 108.7710(10)
_cell_angle_gamma                90
_cell_volume                     1470.88(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3585
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      28.076
_cell_measurement_theta_min      3.163
_shelx_estimated_absorpt_T_max   0.760
_shelx_estimated_absorpt_T_min   0.660
_exptl_absorpt_coefficient_mu    0.808
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6515
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0477 before and 0.0303 after correction.
The Ratio of minimum to maximum transmission is 0.8737.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.36
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8911
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.105
_diffrn_reflns_theta_min         1.715
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_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                2861
_reflns_number_total             3504
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         1.817
_refine_diff_density_min         -1.360
_refine_diff_density_rms         0.167
_refine_ls_extinction_coef       0.032(5)
_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   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3504
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0966
_refine_ls_R_factor_gt           0.0835
_refine_ls_restrained_S_all      1.079
_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)+(0.1518P)²+3.8457P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2395
_refine_ls_wR_factor_ref         0.2525
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Riding coordinates:
 O2W(H2WA,H2WB), O1W(H1WA,H1WB)
2.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C6(H6), C3(H3), C10(H10), C9(H9), C13(H13), C12A(H12A)
;
_atom_sites_solution_hydrogens   mixed
_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
Cr1 Cr 0.31094(6) 0.99607(7) 0.18403(4) 0.0260(3) Uani 1 1 d . . . . .
N1 N 0.4562(4) 0.8775(5) 0.1644(3) 0.0396(9) Uani 1 1 d . . . . .
H1A H 0.494997 0.958346 0.146819 0.047 Uiso 1 1 calc R . . . .
H1B H 0.500398 0.834449 0.214999 0.047 Uiso 1 1 calc R . . . .
C2 C 0.3611(4) 0.4461(6) 0.0653(3) 0.0356(10) Uani 1 1 d . . . . .
N2 N 0.1836(4) 0.8336(6) 0.1150(3) 0.0451(10) Uani 1 1 d . . . . .
C7 C 0.4256(4) 0.7405(6) 0.1009(3) 0.0358(10) Uani 1 1 d . . . . .
C8 C 0.3999(4) 0.5773(6) 0.1260(3) 0.0374(10) Uani 1 1 d . . . . .
H8 H 0.408830 0.555837 0.184541 0.045 Uiso 1 1 calc R . . . .
C6 C 0.4138(4) 0.7718(6) 0.0131(3) 0.0366(10) Uani 1 1 d . . . . .
H6 H 0.431447 0.880851 -0.004146 0.044 Uiso 1 1 calc R . . . .
C4 C 0.3761(4) 0.6412(6) -0.0478(3) 0.0354(10) Uani 1 1 d . . . . .
C3 C 0.3486(5) 0.4774(6) -0.0230(3) 0.0364(10) Uani 1 1 d . . . . .
H3 H 0.322260 0.389951 -0.064477 0.044 Uiso 1 1 calc R . . . .
C11 C 0.0391(5) 0.5715(8) 0.0253(4) 0.0494(13) Uani 1 1 d . . . . .
C10 C 0.0595(8) 0.7168(11) -0.0164(4) 0.091(3) Uani 1 1 d . . . . .
H10 H 0.024750 0.729418 -0.076335 0.109 Uiso 1 1 calc R . . . .
O2W O 0.1433(11) 0.1553(13) 0.2174(6) 0.213(7) Uani 1 1 d . . . . .
H2WA H 0.141665 0.100376 0.171334 0.320 Uiso 1 1 d R . . . .
H2WB H 0.190485 0.107356 0.261534 0.320 Uiso 1 1 d R . . . .
C9 C 0.1319(7) 0.8460(10) 0.0305(4) 0.080(3) Uani 1 1 d . . . . .
H9 H 0.144040 0.944283 0.001019 0.097 Uiso 1 1 calc R . . . .
C13 C 0.1648(6) 0.6905(9) 0.1545(4) 0.068(2) Uani 1 1 d . . . . .
H13 H 0.200935 0.679858 0.214328 0.081 Uiso 1 1 calc R . . . .
O1W O 0.7643(7) 0.9138(10) 0.1444(5) 0.119(3) Uani 1 1 d . . . . .
H1WA H 0.803276 0.843988 0.183358 0.178 Uiso 1 1 d R . . . .
H1WB H 0.757366 0.872878 0.094058 0.178 Uiso 1 1 d R . . . .
C12A C 0.0947(6) 0.5566(10) 0.1120(4) 0.0669(19) Uani 1 1 d . . . . .
H12A H 0.085936 0.457694 0.142474 0.080 Uiso 1 1 calc R . . . .
C5 C 0.3653(4) 0.6730(7) -0.1423(3) 0.0374(10) Uani 1 1 d . . . . .
O3 O 0.3311(4) 0.5427(6) -0.1928(2) 0.0506(10) Uani 1 1 d . . . . .
O4 O 0.3882(4) 0.8178(5) -0.1657(2) 0.0546(10) Uani 1 1 d . . . . .
C1 C 0.3320(4) 0.2699(6) 0.0930(3) 0.0392(10) Uani 1 1 d . . . . .
O1 O 0.3518(4) 0.2438(5) 0.1745(2) 0.0475(9) Uani 1 1 d . . . . .
O2 O 0.2929(4) 0.1537(5) 0.0385(3) 0.0647(13) Uani 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
Cr1 N1 2.148(5) . ?
Cr1 N2 2.049(4) . ?
Cr1 O3 1.946(4) 4_576 ?
Cr1 O1 1.986(4) 1_565 ?
N1 C7 1.432(6) . ?
C2 C8 1.379(7) . ?
C2 C3 1.405(7) . ?
C2 C1 1.505(7) . ?
N2 C9 1.312(7) . ?
N2 C13 1.328(7) . ?
C7 C8 1.385(7) . ?
C7 C6 1.399(6) . ?
C6 C4 1.377(7) . ?
C4 C3 1.395(7) . ?
C4 C5 1.508(6) . ?
C11 C11 1.522(11) 3_565 ?
C11 C10 1.368(9) . ?
C11 C12A 1.353(8) . ?
C10 C9 1.392(9) . ?
C13 C12A 1.382(8) . ?
C5 O3 1.273(6) . ?
C5 O4 1.237(6) . ?
C1 O1 1.275(6) . ?
C1 O2 1.237(6) . ?

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
N2 Cr1 N1 102.21(17) . . ?
O3 Cr1 N1 104.39(17) 4_576 . ?
O3 Cr1 N2 106.61(18) 4_576 . ?
O3 Cr1 O1 105.85(17) 4_576 1_565 ?
O1 Cr1 N1 98.13(16) 1_565 . ?
O1 Cr1 N2 135.60(18) 1_565 . ?
C7 N1 Cr1 111.8(3) . . ?
C8 C2 C3 119.7(4) . . ?
C8 C2 C1 120.5(4) . . ?
C3 C2 C1 119.8(4) . . ?
C9 N2 Cr1 124.1(4) . . ?
C9 N2 C13 117.0(5) . . ?
C13 N2 Cr1 117.9(4) . . ?
C8 C7 N1 119.1(4) . . ?
C8 C7 C6 119.5(4) . . ?
C6 C7 N1 121.2(4) . . ?
C2 C8 C7 120.9(4) . . ?
C4 C6 C7 120.0(4) . . ?
C6 C4 C3 120.6(4) . . ?
C6 C4 C5 120.3(4) . . ?
C3 C4 C5 119.1(4) . . ?
C4 C3 C2 119.3(4) . . ?
C10 C11 C11 120.8(7) . 3_565 ?
C12A C11 C11 121.6(7) . 3_565 ?
C12A C11 C10 117.5(5) . . ?
C11 C10 C9 120.3(6) . . ?
N2 C9 C10 122.2(6) . . ?
N2 C13 C12A 123.9(5) . . ?
C11 C12A C13 119.0(6) . . ?
O3 C5 C4 115.1(4) . . ?
O4 C5 C4 120.0(4) . . ?
O4 C5 O3 124.9(4) . . ?
C5 O3 Cr1 132.9(4) . 4_575 ?
O1 C1 C2 117.6(4) . . ?
O2 C1 C2 120.9(4) . . ?
O2 C1 O1 121.5(5) . . ?
C1 O1 Cr1 105.1(3) . 1_545 ?

_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_zj_CCDC3
_audit_block_doi                 10.5517/ccdc.csd.cc25qjp4
_database_code_depnum_ccdc_archive 'CCDC 2017656'
loop_
_audit_author_name
_audit_author_address
XY 'Liaoning Normal University'
_audit_update_record             
;
2020-07-20 deposited with the CCDC.	2020-12-28 downloaded from the CCDC.
;
_audit_creation_date             2020-07-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C13 H9 N2 Ni O4, 2(H2 O)'
_chemical_formula_sum            'C13 H13 N2 Ni O6'
_chemical_formula_weight         351.96
_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'
Ni Ni 0.3393 1.1124 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.4092(9)
_cell_length_b                   7.6700(5)
_cell_length_c                   16.0912(12)
_cell_angle_alpha                90
_cell_angle_beta                 108.6420(10)
_cell_angle_gamma                90
_cell_volume                     1451.18(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4864
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      31.297
_cell_measurement_theta_min      2.672
_shelx_estimated_absorpt_T_max   0.625
_shelx_estimated_absorpt_T_min   0.542
_exptl_absorpt_coefficient_mu    1.368
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6537
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0650 before and 0.0299 after correction.
The Ratio of minimum to maximum transmission is 0.8760.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             724
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.38
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7163
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         1.732
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_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                2338
_reflns_number_total             2547
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         2.146
_refine_diff_density_min         -0.717
_refine_diff_density_rms         0.107
_refine_ls_extinction_coef       0.0035(13)
_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   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2547
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0583
_refine_ls_restrained_S_all      1.106
_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)+(0.0900P)²+4.5597P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1695
_refine_ls_wR_factor_ref         0.1713
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Riding coordinates:
 O1W(H1WA,H1WB), O2W(H2WA,H2WB)
2.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C5(H5), C4(H4), C2(H2), C1(H1)
;
_atom_sites_solution_hydrogens   mixed
_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
Ni1 Ni 0.31287(5) 0.50485(6) 0.18284(3) 0.0319(3) Uani 1 1 d . . . . .
N1 N 0.4559(4) 0.6218(5) 0.1632(2) 0.0353(9) Uani 1 1 d . . . . .
H1A H 0.500872 0.664127 0.213900 0.042 Uiso 1 1 calc R . . . .
H1B H 0.495011 0.541345 0.144953 0.042 Uiso 1 1 calc R . . . .
C11 C 0.3594(4) 1.0547(6) 0.0653(3) 0.0293(9) Uani 1 1 d . . . . .
C6 C 0.4248(4) 0.7602(5) 0.0997(3) 0.0292(9) Uani 1 1 d . . . . .
C7 C 0.4127(4) 0.7305(5) 0.0118(3) 0.0297(9) Uani 1 1 d . . . . .
H7 H 0.430586 0.621961 -0.005992 0.036 Uiso 1 1 calc R . . . .
C9 C 0.3741(4) 0.8628(6) -0.0490(3) 0.0293(9) Uani 1 1 d . . . . .
C8 C 0.3988(4) 0.9225(5) 0.1260(3) 0.0304(9) Uani 1 1 d . . . . .
H8 H 0.407855 0.942698 0.184793 0.036 Uiso 1 1 calc R . . . .
N2 N 0.1828(3) 0.6651(5) 0.1152(3) 0.0387(9) Uani 1 1 d . . . . .
C10 C 0.3465(4) 1.0249(6) -0.0227(3) 0.0311(10) Uani 1 1 d . . . . .
H10 H 0.319609 1.113048 -0.063814 0.037 Uiso 1 1 calc R . . . .
O1 O 0.2955(4) 1.3473(5) 0.0404(3) 0.0619(12) Uani 1 1 d . . . . .
C12 C 0.3325(4) 1.2303(6) 0.0943(3) 0.0358(10) Uani 1 1 d . . . . .
C3 C 0.0371(4) 0.9287(7) 0.0243(3) 0.0442(12) Uani 1 1 d . . . . .
C5 C 0.1338(6) 0.6576(8) 0.0299(4) 0.0669(19) Uani 1 1 d . . . . .
H5 H 0.147845 0.560807 0.000085 0.080 Uiso 1 1 calc R . . . .
C4 C 0.0629(7) 0.7853(9) -0.0176(4) 0.079(2) Uani 1 1 d . . . . .
H4 H 0.032171 0.775121 -0.078191 0.094 Uiso 1 1 calc R . . . .
C2 C 0.1615(6) 0.8062(9) 0.1556(4) 0.070(2) Uani 1 1 d . . . . .
H2 H 0.196101 0.815355 0.215940 0.084 Uiso 1 1 calc R . . . .
C1 C 0.0910(7) 0.9392(10) 0.1129(4) 0.076(2) Uani 1 1 d . . . . .
H1 H 0.080085 1.035968 0.144045 0.091 Uiso 1 1 calc R . . . .
O2 O 0.3497(3) 1.2546(4) 0.1757(2) 0.0450(9) Uani 1 1 d . . . . .
C13 C 0.3636(4) 0.8318(6) -0.1441(3) 0.0320(10) Uani 1 1 d . . . . .
O3 O 0.3265(3) 0.9612(5) -0.1950(2) 0.0453(9) Uani 1 1 d . . . . .
O4 O 0.3893(3) 0.6895(5) -0.1674(2) 0.0502(10) Uani 1 1 d . . . . .
O1W O 0.2292(8) 0.0814(11) 0.3552(5) 0.147(3) Uani 1 1 d . . . . .
H1WA H 0.256704 -0.015391 0.345886 0.221 Uiso 1 1 d R . . . .
H1WB H 0.258454 0.109259 0.408836 0.221 Uiso 1 1 d R . . . .
O2W O 0.937(3) 0.938(5) 0.2780(10) 0.87(5) Uani 1 1 d . . . . .
H2WA H 0.971263 0.934811 0.332862 1.302 Uiso 1 1 d R . . . .
H2WB H 0.920583 0.834271 0.258941 1.302 Uiso 1 1 d 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
Ni1 N1 2.101(4) . ?
Ni1 N2 2.044(4) . ?
Ni1 O2 1.985(3) 1_545 ?
Ni1 O3 1.937(3) 4_576 ?
N1 C6 1.438(5) . ?
C11 C8 1.384(6) . ?
C11 C10 1.393(6) . ?
C11 C12 1.498(6) . ?
C6 C7 1.392(6) . ?
C6 C8 1.385(6) . ?
C7 C9 1.385(6) . ?
C9 C10 1.390(6) . ?
C9 C13 1.514(6) . ?
N2 C5 1.313(7) . ?
N2 C2 1.331(7) . ?
O1 C12 1.230(6) . ?
C12 O2 1.271(6) . ?
C3 C3 1.481(10) 3_575 ?
C3 C4 1.380(8) . ?
C3 C1 1.369(8) . ?
C5 C4 1.374(8) . ?
C2 C1 1.376(8) . ?
C13 O3 1.275(6) . ?
C13 O4 1.229(6) . ?

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
N2 Ni1 N1 102.97(16) . . ?
O2 Ni1 N1 100.51(15) 1_545 . ?
O2 Ni1 N2 135.08(17) 1_545 . ?
O3 Ni1 N1 106.99(16) 4_576 . ?
O3 Ni1 N2 104.90(16) 4_576 . ?
O3 Ni1 O2 104.01(15) 4_576 1_545 ?
C6 N1 Ni1 111.9(3) . . ?
C8 C11 C10 119.8(4) . . ?
C8 C11 C12 120.2(4) . . ?
C10 C11 C12 120.0(4) . . ?
C7 C6 N1 121.2(4) . . ?
C8 C6 N1 118.9(4) . . ?
C8 C6 C7 119.8(4) . . ?
C9 C7 C6 119.9(4) . . ?
C7 C9 C10 120.3(4) . . ?
C7 C9 C13 119.9(4) . . ?
C10 C9 C13 119.8(4) . . ?
C11 C8 C6 120.5(4) . . ?
C5 N2 Ni1 123.6(4) . . ?
C5 N2 C2 116.6(5) . . ?
C2 N2 Ni1 118.4(3) . . ?
C9 C10 C11 119.8(4) . . ?
O1 C12 C11 120.5(4) . . ?
O1 C12 O2 121.4(4) . . ?
O2 C12 C11 118.1(4) . . ?
C4 C3 C3 122.1(6) . 3_575 ?
C1 C3 C3 121.4(6) . 3_575 ?
C1 C3 C4 116.3(5) . . ?
N2 C5 C4 123.4(5) . . ?
C5 C4 C3 120.3(5) . . ?
N2 C2 C1 123.5(5) . . ?
C3 C1 C2 119.9(6) . . ?
C12 O2 Ni1 103.6(3) . 1_565 ?
O3 C13 C9 115.0(4) . . ?
O4 C13 C9 120.1(4) . . ?
O4 C13 O3 124.9(4) . . ?
C13 O3 Ni1 130.7(3) . 4_575 ?

_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_zj_CCDC4
_audit_block_doi                 10.5517/ccdc.csd.cc25qjjz
_database_code_depnum_ccdc_archive 'CCDC 2017651'
loop_
_audit_author_name
_audit_author_address
XY 'Liaoning Normal University'
_audit_update_record             
;
2020-07-20 deposited with the CCDC.	2020-12-28 downloaded from the CCDC.
;
_audit_creation_date             2020-07-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(H2 O), C13 H9 Fe N2 O4'
_chemical_formula_sum            'C13 H13 Fe N2 O6'
_chemical_formula_weight         349.10
_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'
Fe Fe 0.3463 0.8444 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.228(3)
_cell_length_b                   7.6950(16)
_cell_length_c                   16.114(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.418(4)
_cell_angle_gamma                90
_cell_volume                     1438.5(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1135
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      22.532
_cell_measurement_theta_min      2.664
_shelx_estimated_absorpt_T_max   0.738
_shelx_estimated_absorpt_T_min   0.609
_exptl_absorpt_coefficient_mu    1.079
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6504
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0539 before and 0.0428 after correction.
The Ratio of minimum to maximum transmission is 0.8722.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             716
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0707
_diffrn_reflns_av_unetI/netI     0.0982
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.223
_diffrn_reflns_theta_min         1.755
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_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                1669
_reflns_number_total             3487
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         1.177
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.114
_refine_ls_extinction_coef       0.010(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   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3487
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1601
_refine_ls_R_factor_gt           0.0730
_refine_ls_restrained_S_all      1.022
_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)+(0.1317P)²+0.9128P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2046
_refine_ls_wR_factor_ref         0.2562
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Riding coordinates:
 O2W(H2WA,H2WB), O1W(H1WA,H1WB)
2.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C12(H12), C10(H10), C2(H2), C3(H3), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_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
O2W O 0.570(3) 0.095(4) 0.2190(12) 0.74(4) Uani 1 1 d . . . . .
H2WA H 0.561092 0.040983 0.171318 1.108 Uiso 1 1 d R . . . .
H2WB H 0.617282 0.039683 0.260828 1.108 Uiso 1 1 d R . . . .
O1W O 0.7240(13) 0.0786(14) 0.8573(6) 0.217(6) Uani 1 1 d . . . . .
H1WA H 0.751661 0.136947 0.904101 0.325 Uiso 1 1 d R . . . .
H1WB H 0.761391 -0.015733 0.861091 0.325 Uiso 1 1 d R . . . .
Fe1 Fe 0.81195(9) 0.99565(11) 0.18453(5) 0.0411(4) Uani 1 1 d . . . . .
N1 N 0.9574(6) 0.8757(7) 0.1634(3) 0.0554(17) Uani 1 1 d . . . . .
H1A H 0.997464 0.955415 0.145265 0.066 Uiso 1 1 calc R . . . .
H1B H 1.002800 0.832535 0.213756 0.066 Uiso 1 1 calc R . . . .
C8 C 0.8569(7) 0.4448(8) 0.0660(4) 0.0474(18) Uani 1 1 d . . . . .
C11 C 0.8735(6) 0.6382(8) -0.0484(4) 0.0454(17) Uani 1 1 d . . . . .
C6 C 0.9251(7) 0.7397(8) 0.1003(4) 0.0461(17) Uani 1 1 d . . . . .
C7 C 0.8966(6) 0.5784(8) 0.1261(4) 0.0463(17) Uani 1 1 d . . . . .
H7 H 0.904197 0.559418 0.184650 0.056 Uiso 1 1 calc R . . . .
C12 C 0.9119(7) 0.7677(8) 0.0129(4) 0.0492(18) Uani 1 1 d . . . . .
H12 H 0.929401 0.876356 -0.004857 0.059 Uiso 1 1 calc R . . . .
N2 N 0.6811(6) 0.8388(8) 0.1168(4) 0.0574(16) Uani 1 1 d . . . . .
C10 C 0.8452(7) 0.4771(8) -0.0228(4) 0.0465(17) Uani 1 1 d . . . . .
H10 H 0.818331 0.389791 -0.064148 0.056 Uiso 1 1 calc R . . . .
C2 C 0.5621(9) 0.7152(12) -0.0166(6) 0.093(4) Uani 1 1 d . . . . .
H2 H 0.531151 0.725610 -0.077063 0.112 Uiso 1 1 calc R . . . .
C1 C 0.5378(8) 0.5702(11) 0.0247(5) 0.061(2) Uani 1 1 d . . . . .
C3 C 0.6327(9) 0.8464(11) 0.0316(6) 0.084(3) Uani 1 1 d . . . . .
H3 H 0.646041 0.943852 0.002049 0.101 Uiso 1 1 calc R . . . .
C4 C 0.6562(9) 0.6982(12) 0.1561(6) 0.093(4) Uani 1 1 d . . . . .
H4 H 0.686739 0.691267 0.216656 0.112 Uiso 1 1 calc R . . . .
C5 C 0.5877(10) 0.5620(13) 0.1123(6) 0.095(4) Uani 1 1 d . . . . .
H5 H 0.576221 0.465349 0.143199 0.114 Uiso 1 1 calc R . . . .
C9 C 0.8300(7) 0.2697(9) 0.0944(5) 0.0527(19) Uani 1 1 d . . . . .
O1 O 0.8472(5) 0.2441(6) 0.1755(3) 0.0596(14) Uani 1 1 d . . . . .
O2 O 0.7929(6) 0.1539(6) 0.0397(4) 0.0804(19) Uani 1 1 d . . . . .
C13 C 0.8640(7) 0.6700(9) -0.1429(4) 0.0485(17) Uani 1 1 d . . . . .
O3 O 0.8258(6) 0.5390(7) -0.1937(3) 0.0688(17) Uani 1 1 d . . . . .
O4 O 0.8879(6) 0.8098(7) -0.1669(3) 0.0730(17) Uani 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
Fe1 N1 2.125(7) . ?
Fe1 N2 2.025(6) . ?
Fe1 O1 1.975(5) 1_565 ?
Fe1 O3 1.933(5) 4_576 ?
N1 C6 1.426(8) . ?
C8 C7 1.390(9) . ?
C8 C10 1.415(9) . ?
C8 C9 1.493(9) . ?
C11 C12 1.377(9) . ?
C11 C10 1.385(9) . ?
C11 C13 1.510(8) . ?
C6 C7 1.388(9) . ?
C6 C12 1.383(8) . ?
N2 C3 1.314(9) . ?
N2 C4 1.336(10) . ?
C2 C1 1.379(12) . ?
C2 C3 1.394(11) . ?
C1 C1 1.481(16) 3_665 ?
C1 C5 1.351(12) . ?
C4 C5 1.387(12) . ?
C9 O1 1.271(8) . ?
C9 O2 1.235(8) . ?
C13 O3 1.290(8) . ?
C13 O4 1.210(8) . ?

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
N2 Fe1 N1 102.3(2) . . ?
O1 Fe1 N1 101.3(2) 1_565 . ?
O1 Fe1 N2 133.7(3) 1_565 . ?
O3 Fe1 N1 107.1(2) 4_576 . ?
O3 Fe1 N2 105.4(2) 4_576 . ?
O3 Fe1 O1 104.9(2) 4_576 1_565 ?
C6 N1 Fe1 112.1(5) . . ?
C7 C8 C10 118.4(6) . . ?
C7 C8 C9 121.1(6) . . ?
C10 C8 C9 120.4(6) . . ?
C12 C11 C10 119.7(6) . . ?
C12 C11 C13 120.4(6) . . ?
C10 C11 C13 119.9(6) . . ?
C7 C6 N1 118.8(5) . . ?
C12 C6 N1 121.9(6) . . ?
C12 C6 C7 119.0(6) . . ?
C6 C7 C8 121.2(6) . . ?
C11 C12 C6 121.4(6) . . ?
C3 N2 Fe1 123.7(5) . . ?
C3 N2 C4 115.8(7) . . ?
C4 N2 Fe1 119.1(5) . . ?
C11 C10 C8 120.2(6) . . ?
C1 C2 C3 120.4(8) . . ?
C2 C1 C1 121.6(10) . 3_665 ?
C5 C1 C2 116.6(8) . . ?
C5 C1 C1 121.8(10) . 3_665 ?
N2 C3 C2 123.1(8) . . ?
N2 C4 C5 124.2(8) . . ?
C1 C5 C4 119.8(9) . . ?
O1 C9 C8 118.3(6) . . ?
O2 C9 C8 119.9(6) . . ?
O2 C9 O1 121.8(6) . . ?
C9 O1 Fe1 104.9(4) . 1_545 ?
O3 C13 C11 114.3(6) . . ?
O4 C13 C11 121.1(6) . . ?
O4 C13 O3 124.6(6) . . ?
C13 O3 Fe1 130.6(5) . 4_575 ?

_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_zjzj_pl
_audit_block_doi                 10.5517/ccdc.csd.cc25qjm2
_database_code_depnum_ccdc_archive 'CCDC 2017654'
loop_
_audit_author_name
_audit_author_address
XY 'Liaoning Normal University'
_audit_update_record             
;
2020-07-20 deposited with the CCDC.	2020-12-28 downloaded from the CCDC.
;
_audit_creation_date             2020-07-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 Mn N2 O10'
_chemical_formula_sum            'C16 H16 Mn N2 O10'
_chemical_formula_weight         451.25
_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'
Mn Mn 0.3368 0.7283 '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'

_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      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/n 1'
_space_group_name_Hall           '-P 2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   7.040(4)
_cell_length_b                   10.055(6)
_cell_length_c                   11.499(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.072(10)
_cell_angle_gamma                90
_cell_volume                     810.8(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    945
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      25.574
_cell_measurement_theta_min      2.696
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.883
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6714
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0553 before and 0.0421 after correction.
The Ratio of minimum to maximum transmission is 0.9002.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.848
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             462
_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  0.0450
_diffrn_reflns_av_unetI/netI     0.0612
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5173
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.920
_diffrn_reflns_theta_min         2.025
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_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                1326
_reflns_number_total             2008
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         1.021
_refine_diff_density_min         -0.694
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         2008
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0966
_refine_ls_R_factor_gt           0.0537
_refine_ls_restrained_S_all      1.044
_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)+(0.0561P)²+1.3021P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1394
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Rotating group:
 O5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C1(H1)
2.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   mixed
_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
Mn1 Mn 0.750000 0.27302(8) 0.250000 0.0200(2) Uani 1 2 d S T P . .
O4 O 0.5622(4) 1.1212(2) 0.3044(2) 0.0266(6) Uani 1 1 d . . . . .
O2 O 0.3931(4) 0.5290(3) 0.1195(2) 0.0313(7) Uani 1 1 d . . . . .
O1 O 0.5243(4) 0.4101(2) 0.2687(2) 0.0249(6) Uani 1 1 d . . . . .
N1 N 0.7387(4) 0.7382(3) 0.5865(2) 0.0218(7) Uani 1 1 d . . . . .
H1A H 0.807583 0.663980 0.594050 0.026 Uiso 1 1 calc GR . . . .
H1B H 0.646532 0.735382 0.634631 0.026 Uiso 1 1 calc GR . . . .
H1C H 0.813458 0.808044 0.603979 0.026 Uiso 1 1 calc GR . . . .
C8 C 0.5002(5) 1.0191(3) 0.2465(3) 0.0206(8) Uani 1 1 d . . . . .
C2 C 0.5350(5) 0.8855(3) 0.3042(3) 0.0177(7) Uani 1 1 d . . . . .
C3 C 0.6211(5) 0.8747(3) 0.4179(3) 0.0184(7) Uani 1 1 d . . . . .
H3 H 0.656143 0.950402 0.460997 0.022 Uiso 1 1 calc R . . . .
C4 C 0.6534(5) 0.7501(3) 0.4651(3) 0.0181(7) Uani 1 1 d . . . . .
C5 C 0.6074(5) 0.6350(3) 0.4036(3) 0.0181(7) Uani 1 1 d . . . . .
H5 H 0.632353 0.552234 0.437737 0.022 Uiso 1 1 calc R . . . .
C6 C 0.5229(5) 0.6443(3) 0.2895(3) 0.0172(7) Uani 1 1 d . . . . .
C1 C 0.4855(5) 0.7695(3) 0.2415(3) 0.0189(7) Uani 1 1 d . . . . .
H1 H 0.426369 0.776290 0.166141 0.023 Uiso 1 1 calc R . . . .
C7 C 0.4766(5) 0.5202(3) 0.2201(3) 0.0189(7) Uani 1 1 d . . . . .
O3 O 0.4134(4) 1.0231(3) 0.1472(2) 0.0344(7) Uiso 1 1 d . . . . .
O5 O 0.8302(4) 0.2752(3) 0.4455(2) 0.0344(7) Uiso 1 1 d . . . . .
H5A H 0.777344 0.209618 0.477691 0.052 Uiso 1 1 d GR . . . .
H5B H 0.781692 0.343998 0.475521 0.052 Uiso 1 1 d GR . . . .


_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
Mn1 O4 2.149(3) 2_645 ?
Mn1 O4 2.149(3) 1_545 ?
Mn1 O1 2.129(3) 2_655 ?
Mn1 O1 2.129(3) . ?
Mn1 O5 2.269(3) 2_655 ?
Mn1 O5 2.269(3) . ?
O4 C8 1.278(4) . ?
O2 C7 1.253(4) . ?
O1 C7 1.271(4) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C4 1.474(4) . ?
C8 C2 1.509(5) . ?
C8 O3 1.248(4) . ?
C2 C3 1.396(4) . ?
C2 C1 1.399(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(5) . ?
C4 C5 1.380(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.395(4) . ?
C6 C1 1.390(5) . ?
C6 C7 1.502(5) . ?
C1 H1 0.9300 . ?
O5 H5A 0.8573 . ?
O5 H5B 0.8571 . ?

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
O4 Mn1 O4 89.44(15) 1_545 2_645 ?
O4 Mn1 O5 79.87(10) 2_645 2_655 ?
O4 Mn1 O5 100.94(11) 2_645 . ?
O4 Mn1 O5 100.94(11) 1_545 2_655 ?
O4 Mn1 O5 79.87(10) 1_545 . ?
O1 Mn1 O4 86.95(11) . 1_545 ?
O1 Mn1 O4 166.79(9) . 2_645 ?
O1 Mn1 O4 86.95(11) 2_655 2_645 ?
O1 Mn1 O4 166.79(9) 2_655 1_545 ?
O1 Mn1 O1 99.28(15) . 2_655 ?
O1 Mn1 O5 88.34(10) . 2_655 ?
O1 Mn1 O5 90.93(10) 2_655 2_655 ?
O1 Mn1 O5 90.93(10) . . ?
O1 Mn1 O5 88.34(10) 2_655 . ?
O5 Mn1 O5 178.88(17) 2_655 . ?
C8 O4 Mn1 127.5(2) . 1_565 ?
C7 O1 Mn1 133.6(2) . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C4 N1 H1A 109.5 . . ?
C4 N1 H1B 109.5 . . ?
C4 N1 H1C 109.5 . . ?
O4 C8 C2 116.8(3) . . ?
O3 C8 O4 124.6(3) . . ?
O3 C8 C2 118.6(3) . . ?
C3 C2 C8 121.4(3) . . ?
C3 C2 C1 119.0(3) . . ?
C1 C2 C8 119.5(3) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 118.9(3) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 N1 119.1(3) . . ?
C3 C4 C5 122.5(3) . . ?
C5 C4 N1 118.3(3) . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.1(3) . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C7 119.9(3) . . ?
C1 C6 C5 119.0(3) . . ?
C1 C6 C7 121.1(3) . . ?
C2 C1 H1 119.3 . . ?
C6 C1 C2 121.4(3) . . ?
C6 C1 H1 119.3 . . ?
O2 C7 O1 123.5(3) . . ?
O2 C7 C6 119.6(3) . . ?
O1 C7 C6 117.0(3) . . ?
Mn1 O5 H5A 109.9 . . ?
Mn1 O5 H5B 109.5 . . ?
H5A O5 H5B 104.1 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1B O1 0.89 2.25 2.995(4) 141.2 3_666 yes
N1 H1C O3 0.89 1.89 2.758(4) 165.6 4_676 yes
O5 H5B O2 0.86 2.18 2.814(4) 130.5 4_666 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Mn1 O4 C8 C2 125.0(3) 1_565 . . . ?
Mn1 O4 C8 O3 -55.4(5) 1_565 . . . ?
Mn1 O1 C7 O2 77.2(5) . . . . ?
Mn1 O1 C7 C6 -103.4(3) . . . . ?
O4 C8 C2 C3 3.5(5) . . . . ?
O4 C8 C2 C1 -174.5(3) . . . . ?
N1 C4 C5 C6 178.7(3) . . . . ?
C8 C2 C3 C4 -178.5(3) . . . . ?
C8 C2 C1 C6 177.1(3) . . . . ?
C2 C3 C4 N1 -178.0(3) . . . . ?
C2 C3 C4 C5 1.3(5) . . . . ?
C3 C2 C1 C6 -1.0(5) . . . . ?
C3 C4 C5 C6 -0.7(5) . . . . ?
C4 C5 C6 C1 -0.7(5) . . . . ?
C4 C5 C6 C7 178.4(3) . . . . ?
C5 C6 C1 C2 1.6(5) . . . . ?
C5 C6 C7 O2 176.9(3) . . . . ?
C5 C6 C7 O1 -2.5(5) . . . . ?
C1 C2 C3 C4 -0.5(5) . . . . ?
C1 C6 C7 O2 -4.0(5) . . . . ?
C1 C6 C7 O1 176.6(3) . . . . ?
C7 C6 C1 C2 -177.5(3) . . . . ?
O3 C8 C2 C3 -176.2(3) . . . . ?
O3 C8 C2 C1 5.8(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
