# 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_1
_audit_block_doi                 10.5517/ccdc.csd.cc28my40
_database_code_depnum_ccdc_archive 'CCDC 2104532'
loop_
_audit_author_name
_audit_author_address
'Lishan Gong'
;College of Chemistry and Chemical Engineering, Central South University, Changsha, Hunan, China
China
;
_audit_update_record             
;
2021-08-20 deposited with the CCDC.	2021-11-02 downloaded from the CCDC.
;
_audit_creation_date             2021-04-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 H13 N4 O5 Zn, 2(N O3)'
_chemical_formula_sum            'C2 H13 N6 O11 Zn'
_chemical_formula_weight         362.55
_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.5599(2)
_cell_length_b                   8.4029(2)
_cell_length_c                   13.1796(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.3160(10)
_cell_angle_gamma                90
_cell_volume                     1266.76(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8465
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      30.86
_cell_measurement_theta_min      3.01
_shelx_estimated_absorpt_T_max   0.433
_shelx_estimated_absorpt_T_min   0.433
_exptl_absorpt_coefficient_mu    2.010
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.5637
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0967 before and 0.0348 after correction.
The Ratio of minimum to maximum transmission is 0.7553.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dull whiteish colourless'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.901
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             740
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0145
_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       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14447
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.099
_diffrn_reflns_theta_min         2.533
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2311
_reflns_number_total             2520
_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 v8.27A (Bruker, 2012)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.844
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2520
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0231
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0333P)²+0.7717P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0619
_refine_ls_wR_factor_ref         0.0634
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All O(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 Zn01-H00G \\sim Zn01-H00H
 with sigma of 0.02
 O00C-N00F \\sim O2-N00F
 with sigma of 0.02
 N00F-O00K \\sim N00F-O00L
 with sigma of 0.02
3. Rigid bond restraints
 O1, N00A, N009
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
4. Uiso/Uaniso restraints and constraints
N009 \\sim O1 \\sim N00A: within 2A with sigma of 0.001 and sigma for terminal
atoms of 0.002 within 2A
5. Others
 Sof(O2)=Sof(O00L)=1-FVAR(1)
 Sof(O00C)=Sof(O00K)=FVAR(1)
6.a Free rotating group:
 O008(H00G,H00H)
6.b Rotating group:
 O003(H00A,H00B), O004(H00C,H00D), O006(H00E,H00F)
6.c Aromatic/amide H refined with riding coordinates:
 O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_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
Zn01 Zn 0.39962(2) 0.80701(2) 0.66748(2) 0.02286(9) Uani 1 1 d D . . . .
O1 O 0.26955(11) 0.53092(15) 0.74531(10) 0.0267(3) Uani 1 1 d . U . . .
H1 H 0.203365 0.572660 0.705742 0.032 Uiso 1 1 calc R U . . .
O003 O 0.48830(12) 0.90648(18) 0.80244(11) 0.0343(3) Uani 1 1 d . . . . .
H00A H 0.513801 0.998557 0.789706 0.051 Uiso 1 1 d R U . . .
H00B H 0.440118 0.924051 0.844455 0.051 Uiso 1 1 d R U . . .
O004 O 0.32188(14) 0.69144(16) 0.53723(11) 0.0343(3) Uani 1 1 d . . . . .
H00C H 0.351489 0.724756 0.485583 0.051 Uiso 1 1 d R U . . .
H00D H 0.339626 0.593043 0.541312 0.051 Uiso 1 1 d R U . . .
O005 O 0.32023(13) 0.36526(19) 0.52985(14) 0.0424(4) Uani 1 1 d . . . . .
O006 O 0.40998(13) 1.00855(17) 0.58146(12) 0.0401(4) Uani 1 1 d . . . . .
H00E H 0.464947 1.068999 0.610299 0.060 Uiso 1 1 d R U . . .
H00F H 0.347864 1.064678 0.581114 0.060 Uiso 1 1 d R U . . .
O007 O 0.13561(13) 0.41267(19) 0.52455(12) 0.0393(4) Uani 1 1 d . . . . .
O008 O 0.56687(13) 0.7438(2) 0.63843(13) 0.0443(4) Uani 1 1 d G . . . .
H00G H 0.630969 0.766308 0.675813 0.066 Uiso 1 1 d DG U . . .
H00H H 0.587053 0.706119 0.583801 0.066 Uiso 1 1 d DG U . . .
N009 N 0.38148(13) 0.59537(18) 0.75445(12) 0.0257(3) Uani 1 1 d . U . . .
N00A N 0.27272(13) 0.39350(18) 0.80515(12) 0.0255(3) Uani 1 1 d . U . . .
O00B O 0.19733(16) 0.17139(18) 0.51566(14) 0.0463(4) Uani 1 1 d . . . . .
O00C O 0.7397(11) 0.779(2) 0.7942(18) 0.053(3) Uani 0.46(4) 1 d D . P A 1
O00D O 0.85952(19) 0.6650(2) 0.70521(13) 0.0580(5) Uani 1 1 d . . . . .
N00E N 0.21708(15) 0.31667(19) 0.52344(13) 0.0301(4) Uani 1 1 d . . . . .
N00F N 0.83352(17) 0.7152(2) 0.78577(14) 0.0392(4) Uani 1 1 d D . . . .
N00G N 0.56287(17) 0.5303(3) 0.84895(18) 0.0450(5) Uani 1 1 d . . . . .
C00H C 0.44937(16) 0.5053(2) 0.81705(14) 0.0251(4) Uani 1 1 d . . . . .
N00I N 0.41871(19) 0.2601(3) 0.91444(17) 0.0403(5) Uani 1 1 d . . . . .
C00J C 0.37992(16) 0.3763(2) 0.84971(14) 0.0238(4) Uani 1 1 d . . . . .
O00K O 0.9127(15) 0.720(3) 0.8629(11) 0.060(4) Uani 0.46(4) 1 d D . P A 1
H00K H 0.371(2) 0.196(3) 0.934(2) 0.037(7) Uiso 1 1 d . . . . .
H00L H 0.477(2) 0.259(3) 0.941(2) 0.036(7) Uiso 1 1 d . . . . .
H00I H 0.592(2) 0.611(4) 0.831(2) 0.050(8) Uiso 1 1 d . . . . .
H00J H 0.602(3) 0.467(4) 0.883(2) 0.054(8) Uiso 1 1 d . . . . .
O2 O 0.7543(15) 0.815(3) 0.7850(14) 0.059(4) Uani 0.54(4) 1 d D . P A 2
O00L O 0.8739(18) 0.648(3) 0.8674(6) 0.064(4) Uani 0.54(4) 1 d D . P A 2


_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 O003 2.0942(14) . ?
Zn01 O004 2.0618(14) . ?
Zn01 O006 2.0511(14) . ?
Zn01 O008 2.0930(15) . ?
Zn01 N009 2.1424(15) . ?
Zn01 N00A 2.1990(15) 2_556 ?
O1 H1 0.9300 . ?
O1 N009 1.3917(19) . ?
O1 N00A 1.3959(19) . ?
O003 H00A 0.8532 . ?
O003 H00B 0.8532 . ?
O004 H00C 0.8522 . ?
O004 H00D 0.8517 . ?
O005 N00E 1.252(2) . ?
O006 H00E 0.8582 . ?
O006 H00F 0.8586 . ?
O007 N00E 1.242(2) . ?
O008 H00G 0.8498 . ?
O008 H00H 0.8494 . ?
N009 C00H 1.297(2) . ?
N00A C00J 1.300(2) . ?
O00B N00E 1.243(2) . ?
O00C N00F 1.230(11) . ?
O00D N00F 1.220(3) . ?
N00F O00K 1.266(7) . ?
N00F O2 1.243(9) . ?
N00F O00L 1.243(6) . ?
N00G C00H 1.335(3) . ?
N00G H00I 0.81(3) . ?
N00G H00J 0.80(3) . ?
C00H C00J 1.451(3) . ?
N00I C00J 1.331(3) . ?
N00I H00K 0.84(3) . ?
N00I H00L 0.72(3) . ?

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
O003 Zn01 N009 87.17(6) . . ?
O003 Zn01 N00A 94.16(6) . 2_556 ?
O004 Zn01 O003 174.85(6) . . ?
O004 Zn01 O008 91.78(7) . . ?
O004 Zn01 N009 89.42(6) . . ?
O004 Zn01 N00A 89.78(6) . 2_556 ?
O006 Zn01 O003 94.56(6) . . ?
O006 Zn01 O004 88.96(6) . . ?
O006 Zn01 O008 88.81(7) . . ?
O006 Zn01 N009 177.64(6) . . ?
O006 Zn01 N00A 86.82(6) . 2_556 ?
O008 Zn01 O003 84.55(6) . . ?
O008 Zn01 N009 92.96(7) . . ?
O008 Zn01 N00A 175.33(7) . 2_556 ?
N009 Zn01 N00A 91.46(6) . 2_556 ?
N009 O1 H1 125.5 . . ?
N009 O1 N00A 108.96(12) . . ?
N00A O1 H1 125.5 . . ?
Zn01 O003 H00A 109.6 . . ?
Zn01 O003 H00B 109.6 . . ?
H00A O003 H00B 104.3 . . ?
Zn01 O004 H00C 109.5 . . ?
Zn01 O004 H00D 109.4 . . ?
H00C O004 H00D 104.4 . . ?
Zn01 O006 H00E 110.0 . . ?
Zn01 O006 H00F 109.9 . . ?
H00E O006 H00F 104.0 . . ?
Zn01 O008 H00G 126.0 . . ?
Zn01 O008 H00H 128.6 . . ?
H00G O008 H00H 104.5 . . ?
O1 N009 Zn01 116.00(10) . . ?
C00H N009 Zn01 136.70(13) . . ?
C00H N009 O1 107.30(14) . . ?
O1 N00A Zn01 114.56(10) . 2_546 ?
C00J N00A Zn01 135.73(13) . 2_546 ?
C00J N00A O1 107.00(14) . . ?
O007 N00E O005 120.27(17) . . ?
O007 N00E O00B 120.55(18) . . ?
O00B N00E O005 119.18(18) . . ?
O00C N00F O00K 117.3(12) . . ?
O00D N00F O00C 124.1(11) . . ?
O00D N00F O00K 118.0(6) . . ?
O00D N00F O2 120.0(9) . . ?
O00D N00F O00L 119.2(5) . . ?
O2 N00F O00L 119.9(10) . . ?
C00H N00G H00I 118.1(19) . . ?
C00H N00G H00J 122(2) . . ?
H00I N00G H00J 120(3) . . ?
N009 C00H N00G 125.81(18) . . ?
N009 C00H C00J 108.35(16) . . ?
N00G C00H C00J 125.79(18) . . ?
C00J N00I H00K 119.3(17) . . ?
C00J N00I H00L 122(2) . . ?
H00K N00I H00L 118(3) . . ?
N00A C00J C00H 108.38(16) . . ?
N00A C00J N00I 125.56(18) . . ?
N00I C00J C00H 126.06(18) . . ?

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
Zn01 N009 C00H N00G 2.5(3) . . . . ?
Zn01 N009 C00H C00J -179.75(14) . . . . ?
Zn01 N00A C00J C00H -160.20(14) 2_546 . . . ?
Zn01 N00A C00J N00I 19.6(3) 2_546 . . . ?
O1 N009 C00H N00G -177.3(2) . . . . ?
O1 N009 C00H C00J 0.4(2) . . . . ?
O1 N00A C00J C00H -0.7(2) . . . . ?
O1 N00A C00J N00I 179.1(2) . . . . ?
N009 O1 N00A Zn01 165.40(11) . . . 2_546 ?
N009 O1 N00A C00J 1.02(19) . . . . ?
N009 C00H C00J N00A 0.2(2) . . . . ?
N009 C00H C00J N00I -179.6(2) . . . . ?
N00A O1 N009 Zn01 179.24(11) . . . . ?
N00A O1 N009 C00H -0.90(19) . . . . ?
N00G C00H C00J N00A 177.9(2) . . . . ?
N00G C00H C00J N00I -1.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: ????'
