# 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 2023

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

data_wq-2231854_auto
_database_code_depnum_ccdc_archive 'CCDC 2286914'
loop_
_audit_author_name
_audit_author_address
'Qin Wang'
;FAFU Universoity
China
;
_audit_update_record             
;
2023-11-22 deposited with the CCDC.	2023-11-28 downloaded from the CCDC.
;
_audit_creation_date             2023-11-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H11 N10 O2 Zn2, N O3'
_chemical_formula_sum            'C4 H11 N11 O5 Zn2'
_chemical_formula_weight         423.98
_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                   8.2150(3)
_cell_length_b                   17.8423(6)
_cell_length_c                   8.6996(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.560(3)
_cell_angle_gamma                90
_cell_volume                     1228.41(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7069
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      29.4100
_cell_measurement_theta_min      2.2910
_shelx_estimated_absorpt_T_max   0.743
_shelx_estimated_absorpt_T_min   0.627
_exptl_absorpt_coefficient_mu    3.957
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    2.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.827
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10364
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.827
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.289
_diffrn_reflns_theta_min         2.283
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.827
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00  36.00   0.50    0.05    --   10.52 -57.00   0.00  198
  2  ω     21.00  46.00   0.50    0.05    --   10.52-127.00 109.00   50
  3  ω     53.00  78.00   0.50    0.05    --   10.52-143.00 -60.00   50
  4  ω    -69.00  22.00   0.50    0.05    --   10.52 -19.00-120.00  182
  5  ω    -10.00  15.00   0.50    0.05    --  -11.30 -99.00 -60.00   50
  6  ω    -10.00  27.00   0.50    0.05    --  -11.30 -99.00-150.00   74
  7  ω    -72.00 -47.00   0.50    0.05    --  -11.30 127.00-174.00   50
  8  ω    -66.00 -41.00   0.50    0.05    --  -11.30 143.00  -4.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0212699000
_diffrn_orient_matrix_UB_12      0.0334497000
_diffrn_orient_matrix_UB_13      0.0449788000
_diffrn_orient_matrix_UB_21      0.0414675000
_diffrn_orient_matrix_UB_22      -0.0214047000
_diffrn_orient_matrix_UB_23      0.0679222000
_diffrn_orient_matrix_UB_31      0.0764584000
_diffrn_orient_matrix_UB_32      0.0023226000
_diffrn_orient_matrix_UB_33      -0.0229061000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2504
_reflns_number_total             2774
_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       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.685
_refine_diff_density_min         -0.796
_refine_diff_density_rms         0.144
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2774
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0433
_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)+11.6514P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.0922
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
O5: within 2A with sigma of 0.001 and sigma for terminal atoms of 0.002 within
2A
3.a Rotating group:
 N13(H13a,H13b), N25(H25a,H25b), N15(H15a), N23(H23a,H23b)
3.b X=CH2 refined with riding coordinates:
 O1W(H1Wa,H1Wb)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
Zn2 Zn 0.84866(6) 0.37677(3) 0.69865(6) 0.00683(13) Uani 1 1 d . . . . .
Zn1 Zn 0.60046(6) 0.42520(3) 0.93049(6) 0.00629(13) Uani 1 1 d . . . . .
O5 O 0.6808(4) 0.44394(19) 0.7415(4) 0.0093(7) Uani 1 1 d . . . A 1
H5 H 0.613(7) 0.452(3) 0.669(7) 0.014 Uiso 1 1 d . U . B 1
N11 N 0.3543(4) 0.4317(2) 0.8921(4) 0.0077(7) Uani 1 1 d . . . . .
N22 N 0.7044(4) 0.3245(2) 0.9728(4) 0.0075(7) Uani 1 1 d . . . . .
N12 N 0.2772(4) 0.4993(2) 0.9139(4) 0.0066(7) Uani 1 1 d . . . . .
O3 O 0.2996(5) 0.3457(2) 0.2416(5) 0.0280(9) Uani 1 1 d . . . . .
O2 O 0.5343(4) 0.4061(2) 0.2722(5) 0.0258(9) Uani 1 1 d . . . . .
O1W O 0.8351(5) 0.4517(2) 0.4744(4) 0.0252(9) Uani 1 1 d . . . . .
H1WA H 0.761245 0.493686 0.452783 0.038 Uiso 1 1 calc R U . . .
H1WB H 0.903494 0.440194 0.405190 0.038 Uiso 1 1 calc R U . . .
N21 N 0.8453(5) 0.3102(2) 0.9133(4) 0.0087(8) Uani 1 1 d . . . . .
N13 N -0.0050(5) 0.5449(2) 0.8287(5) 0.0129(8) Uani 1 1 d . . . . .
H13A H -0.103236 0.524836 0.830320 0.015 Uiso 1 1 d R U . . .
H13B H 0.025954 0.577156 0.908609 0.015 Uiso 1 1 d R U . . .
O4 O 0.4004(5) 0.4100(3) 0.4584(5) 0.0337(10) Uani 1 1 d . . . . .
N14 N 0.0777(4) 0.4210(2) 0.7818(4) 0.0081(7) Uani 1 1 d . . . . .
N25 N 1.0317(5) 0.2052(2) 0.9368(5) 0.0122(8) Uani 1 1 d . . . . .
H25A H 0.999806 0.164414 0.878420 0.015 Uiso 1 1 d R U . . .
H25B H 1.086167 0.235184 0.886291 0.015 Uiso 1 1 d R U . . .
N24 N 0.7961(5) 0.2094(2) 1.0471(5) 0.0100(8) Uani 1 1 d . . . . .
N1 N 0.4109(5) 0.3874(3) 0.3243(6) 0.0216(10) Uani 1 1 d . . . . .
C11 C 0.1141(5) 0.4907(2) 0.8444(5) 0.0055(8) Uani 1 1 d . . . . .
N15 N 0.2468(5) 0.3127(2) 0.7787(5) 0.0129(8) Uani 1 1 d . . . . .
H15A H 0.197277 0.304897 0.676828 0.015 Uiso 1 1 d R U . . .
N23 N 0.5466(5) 0.2519(2) 1.1118(5) 0.0138(8) Uani 1 1 d . . . . .
H23A H 0.574753 0.219431 1.190927 0.017 Uiso 1 1 d R U . . .
H23B H 0.520073 0.294971 1.148577 0.017 Uiso 1 1 d R U . . .
C22 C 0.8934(5) 0.2413(3) 0.9610(5) 0.0079(9) Uani 1 1 d . . . . .
C12 C 0.2306(5) 0.3868(3) 0.8148(5) 0.0076(8) Uani 1 1 d . . . . .
C21 C 0.6797(5) 0.2629(3) 1.0472(5) 0.0090(9) Uani 1 1 d . . . . .
H15B H 0.350(8) 0.295(4) 0.804(7) 0.027(17) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn2 O5 1.937(3) . ?
Zn2 O1W 2.343(4) . ?
Zn2 N21 2.219(4) . ?
Zn2 N14 1.989(4) 1_655 ?
Zn2 N24 1.996(4) 4_565 ?
Zn1 O5 1.957(3) . ?
Zn1 N11 1.963(4) . ?
Zn1 N22 1.982(4) . ?
Zn1 N12 1.982(4) 3_667 ?
O5 H5 0.73(6) . ?
N11 N12 1.399(5) . ?
N11 C12 1.326(6) . ?
N22 N21 1.412(5) . ?
N22 C21 1.319(6) . ?
N12 C11 1.322(5) . ?
O3 N1 1.247(6) . ?
O2 N1 1.261(6) . ?
O1W H1WA 0.9500 . ?
O1W H1WB 0.9500 . ?
N21 C22 1.323(6) . ?
N13 H13A 0.8866 . ?
N13 H13B 0.8856 . ?
N13 C11 1.356(6) . ?
O4 N1 1.260(6) . ?
N14 C11 1.360(6) . ?
N14 C12 1.355(6) . ?
N25 H25A 0.8858 . ?
N25 H25B 0.8858 . ?
N25 C22 1.372(6) . ?
N24 C22 1.358(6) . ?
N24 C21 1.350(6) . ?
N15 H15A 0.8816 . ?
N15 C12 1.375(6) . ?
N15 H15B 0.88(6) . ?
N23 H23A 0.8821 . ?
N23 H23B 0.8818 . ?
N23 C21 1.371(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
O5 Zn2 O1W 85.98(14) . . ?
O5 Zn2 N21 89.93(14) . . ?
O5 Zn2 N14 109.74(15) . 1_655 ?
O5 Zn2 N24 124.39(15) . 4_565 ?
N21 Zn2 O1W 175.85(14) . . ?
N14 Zn2 O1W 84.57(14) 1_655 . ?
N14 Zn2 N21 97.50(14) 1_655 . ?
N14 Zn2 N24 124.16(15) 1_655 4_565 ?
N24 Zn2 O1W 86.37(15) 4_565 . ?
N24 Zn2 N21 95.38(16) 4_565 . ?
O5 Zn1 N11 114.28(15) . . ?
O5 Zn1 N22 94.88(14) . . ?
O5 Zn1 N12 103.53(15) . 3_667 ?
N11 Zn1 N22 117.26(15) . . ?
N11 Zn1 N12 112.77(15) . 3_667 ?
N22 Zn1 N12 112.05(15) . 3_667 ?
Zn2 O5 Zn1 118.29(17) . . ?
Zn2 O5 H5 112(5) . . ?
Zn1 O5 H5 114(4) . . ?
N12 N11 Zn1 120.7(3) . . ?
C12 N11 Zn1 131.7(3) . . ?
C12 N11 N12 106.0(3) . . ?
N21 N22 Zn1 116.8(3) . . ?
C21 N22 Zn1 137.0(3) . . ?
C21 N22 N21 106.2(4) . . ?
N11 N12 Zn1 120.9(3) . 3_667 ?
C11 N12 Zn1 131.1(3) . 3_667 ?
C11 N12 N11 106.1(3) . . ?
Zn2 O1W H1WA 120.0 . . ?
Zn2 O1W H1WB 120.0 . . ?
H1WA O1W H1WB 120.0 . . ?
N22 N21 Zn2 114.1(3) . . ?
C22 N21 Zn2 133.7(3) . . ?
C22 N21 N22 104.9(3) . . ?
H13A N13 H13B 108.7 . . ?
C11 N13 H13A 110.2 . . ?
C11 N13 H13B 109.6 . . ?
C11 N14 Zn2 126.4(3) . 1_455 ?
C12 N14 Zn2 129.1(3) . 1_455 ?
C12 N14 C11 103.6(4) . . ?
H25A N25 H25B 108.8 . . ?
C22 N25 H25A 110.1 . . ?
C22 N25 H25B 110.0 . . ?
C22 N24 Zn2 129.2(3) . 4_566 ?
C21 N24 Zn2 124.9(3) . 4_566 ?
C21 N24 C22 103.1(4) . . ?
O3 N1 O2 119.1(5) . . ?
O3 N1 O4 120.2(5) . . ?
O4 N1 O2 120.6(5) . . ?
N12 C11 N13 125.4(4) . . ?
N12 C11 N14 112.1(4) . . ?
N13 C11 N14 122.5(4) . . ?
H15A N15 H15B 110.6 . . ?
C12 N15 H15A 109.5 . . ?
C12 N15 H15B 116(4) . . ?
H23A N23 H23B 109.1 . . ?
C21 N23 H23A 110.0 . . ?
C21 N23 H23B 109.0 . . ?
N21 C22 N25 125.3(4) . . ?
N21 C22 N24 113.1(4) . . ?
N24 C22 N25 121.5(4) . . ?
N11 C12 N14 112.1(4) . . ?
N11 C12 N15 126.1(4) . . ?
N14 C12 N15 121.7(4) . . ?
N22 C21 N24 112.7(4) . . ?
N22 C21 N23 124.4(4) . . ?
N24 C21 N23 122.8(4) . . ?

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
Zn2 N21 C22 N25 36.2(7) . . . . ?
Zn2 N21 C22 N24 -147.3(3) . . . . ?
Zn2 N14 C11 N12 169.2(3) 1_455 . . . ?
Zn2 N14 C11 N13 -13.7(6) 1_455 . . . ?
Zn2 N14 C12 N11 -170.0(3) 1_455 . . . ?
Zn2 N14 C12 N15 6.2(6) 1_455 . . . ?
Zn2 N24 C22 N21 -159.7(3) 4_566 . . . ?
Zn2 N24 C22 N25 16.9(6) 4_566 . . . ?
Zn2 N24 C21 N22 160.0(3) 4_566 . . . ?
Zn2 N24 C21 N23 -22.9(6) 4_566 . . . ?
Zn1 N11 N12 Zn1 -28.3(4) . . . 3_667 ?
Zn1 N11 N12 C11 165.7(3) . . . . ?
Zn1 N11 C12 N14 -164.2(3) . . . . ?
Zn1 N11 C12 N15 19.8(7) . . . . ?
Zn1 N22 N21 Zn2 -27.4(4) . . . . ?
Zn1 N22 N21 C22 178.1(3) . . . . ?
Zn1 N22 C21 N24 -176.8(3) . . . . ?
Zn1 N22 C21 N23 6.1(8) . . . . ?
Zn1 N12 C11 N13 20.5(7) 3_667 . . . ?
Zn1 N12 C11 N14 -162.4(3) 3_667 . . . ?
N11 N12 C11 N13 -175.4(4) . . . . ?
N11 N12 C11 N14 1.7(5) . . . . ?
N22 N21 C22 N25 -176.6(4) . . . . ?
N22 N21 C22 N24 -0.1(5) . . . . ?
N12 N11 C12 N14 1.2(5) . . . . ?
N12 N11 C12 N15 -174.8(4) . . . . ?
N21 N22 C21 N24 2.1(5) . . . . ?
N21 N22 C21 N23 -174.9(4) . . . . ?
C11 N14 C12 N11 -0.2(5) . . . . ?
C11 N14 C12 N15 176.0(4) . . . . ?
C22 N24 C21 N22 -2.2(5) . . . . ?
C22 N24 C21 N23 175.0(4) . . . . ?
C12 N11 N12 Zn1 164.3(3) . . . 3_667 ?
C12 N11 N12 C11 -1.7(4) . . . . ?
C12 N14 C11 N12 -1.0(5) . . . . ?
C12 N14 C11 N13 176.2(4) . . . . ?
C21 N22 N21 Zn2 153.4(3) . . . . ?
C21 N22 N21 C22 -1.2(5) . . . . ?
C21 N24 C22 N21 1.4(5) . . . . ?
C21 N24 C22 N25 178.0(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.783
_oxdiff_exptl_absorpt_empirical_full_min 0.558
