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

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

data_1-alpha
_database_code_depnum_ccdc_archive 'CCDC 2160142'
loop_
_audit_author_name
_audit_author_address
'Ai-Xin Zhu'
;Yunnan Normal University
China
;
_audit_update_record             
;
2022-03-19 deposited with the CCDC.	2022-06-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H21 N7 O5 Zn'
_chemical_formula_weight         528.83

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.9713(6)
_cell_length_b                   12.0179(10)
_cell_length_c                   14.2464(11)
_cell_angle_alpha                72.986(2)
_cell_angle_beta                 87.232(2)
_cell_angle_gamma                83.640(2)
_cell_volume                     1134.15(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6298
_cell_measurement_theta_min      2.941
_cell_measurement_theta_max      25.066

_exptl_crystal_description       diamond
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.133
_shelx_estimated_absorpt_T_min   0.742
_shelx_estimated_absorpt_T_max   0.805
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6970
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0510 before and 0.0439 after correction.
The Ratio of minimum to maximum transmission is 0.9353.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14919
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.940
_diffrn_reflns_theta_max         25.449
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4178
_reflns_number_gt                3312
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0852P)²+1.4739P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4178
_refine_ls_number_parameters     316
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0564
_refine_ls_wR_factor_ref         0.1490
_refine_ls_wR_factor_gt          0.1384
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.76818(7) 0.18720(4) 0.21184(3) 0.02534(18) Uani 1 1 d . . . . .
N1 N 0.4326(5) -0.0766(3) 0.7872(2) 0.0256(7) Uani 1 1 d . . . . .
N2 N 0.4232(5) 0.0128(3) 0.8314(3) 0.0320(8) Uani 1 1 d . . . . .
N3 N 0.6576(5) 0.0338(3) 0.7208(2) 0.0242(7) Uani 1 1 d . . . . .
N4 N 1.0023(5) 0.8389(3) -0.1253(2) 0.0254(7) Uani 1 1 d . . . . .
N5 N 0.9733(5) 0.9153(3) -0.0685(3) 0.0286(8) Uani 1 1 d . . . . .
N6 N 0.7626(5) 0.7853(3) -0.0253(2) 0.0248(7) Uani 1 1 d . . . . .
N7 N 0.5009(14) 0.5053(7) 0.6271(5) 0.114(3) Uani 1 1 d . U . . .
O1 O 0.7825(5) 0.1463(3) 0.3548(2) 0.0383(8) Uani 1 1 d . . . . .
O2 O 1.0724(5) 0.2105(3) 0.3321(2) 0.0491(9) Uani 1 1 d . . . . .
O3 O 0.7275(5) 0.3568(3) 0.1514(2) 0.0388(8) Uani 1 1 d . . . . .
O4 O 0.4183(5) 0.3397(3) 0.1926(3) 0.0465(9) Uani 1 1 d . . . . .
O5 O 0.4565(9) 0.3224(4) 0.6903(5) 0.107(2) Uani 1 1 d . U . . .
C1 C 0.5727(6) -0.0616(4) 0.7229(3) 0.0309(10) Uani 1 1 d . . . . .
H1A H 0.609202 -0.110319 0.683652 0.037 Uiso 1 1 calc R U . . .
C2 C 0.5594(6) 0.0762(4) 0.7892(3) 0.0317(10) Uani 1 1 d . . . . .
H2A H 0.586423 0.143017 0.804322 0.038 Uiso 1 1 calc R U . . .
C3 C 0.8133(6) 0.0833(3) 0.6572(3) 0.0257(9) Uani 1 1 d . . . . .
C4 C 0.7993(6) 0.1001(4) 0.5574(3) 0.0281(9) Uani 1 1 d . . . . .
H4A H 0.692470 0.079242 0.532276 0.034 Uiso 1 1 calc R U . . .
C5 C 0.9484(6) 0.1489(3) 0.4949(3) 0.0275(9) Uani 1 1 d . . . . .
C6 C 1.1046(6) 0.1795(4) 0.5347(3) 0.0345(10) Uani 1 1 d . . . . .
H6A H 1.204147 0.211936 0.493436 0.041 Uiso 1 1 calc R U . . .
C7 C 1.1158(7) 0.1630(4) 0.6345(3) 0.0404(12) Uani 1 1 d . . . . .
H7A H 1.221196 0.184911 0.659987 0.048 Uiso 1 1 calc R U . . .
C8 C 0.9692(6) 0.1137(4) 0.6962(3) 0.0334(10) Uani 1 1 d . . . . .
H8A H 0.976054 0.101149 0.763607 0.040 Uiso 1 1 calc R U . . .
C9 C 0.9372(6) 0.1705(4) 0.3853(3) 0.0313(10) Uani 1 1 d . . . . .
C10 C 0.8755(6) 0.7627(4) -0.0985(3) 0.0280(9) Uani 1 1 d . . . . .
H10A H 0.864741 0.702153 -0.125757 0.034 Uiso 1 1 calc R U . . .
C11 C 0.8290(6) 0.8808(4) -0.0097(3) 0.0283(9) Uani 1 1 d . . . . .
H11A H 0.777807 0.916616 0.036913 0.034 Uiso 1 1 calc R U . . .
C12 C 0.6118(6) 0.7168(3) 0.0268(3) 0.0243(9) Uani 1 1 d . . . . .
C13 C 0.6548(6) 0.5971(4) 0.0653(3) 0.0276(9) Uani 1 1 d . . . . .
H13A H 0.779128 0.562524 0.059395 0.033 Uiso 1 1 calc R U . . .
C14 C 0.5096(6) 0.5287(4) 0.1133(3) 0.0262(9) Uani 1 1 d . . . . .
C15 C 0.3269(6) 0.5825(4) 0.1213(3) 0.0296(10) Uani 1 1 d . . . . .
H15A H 0.229361 0.537620 0.152739 0.036 Uiso 1 1 calc R U . . .
C16 C 0.2866(6) 0.7017(4) 0.0835(3) 0.0357(10) Uani 1 1 d . . . . .
H16A H 0.162942 0.736563 0.090654 0.043 Uiso 1 1 calc R U . . .
C17 C 0.4300(6) 0.7706(4) 0.0346(3) 0.0291(9) Uani 1 1 d . . . . .
H17A H 0.403007 0.851044 0.007983 0.035 Uiso 1 1 calc R U . . .
C18 C 0.5517(7) 0.3988(4) 0.1553(3) 0.0316(10) Uani 1 1 d . . . . .
C19 C 0.7340(11) 0.4394(10) 0.6206(7) 0.124(4) Uani 1 1 d . U . . .
H19A H 0.818320 0.498310 0.590214 0.186 Uiso 1 1 calc R U . . .
H19B H 0.777701 0.398091 0.685585 0.186 Uiso 1 1 calc R U . . .
H19C H 0.734826 0.385556 0.582340 0.186 Uiso 1 1 calc R U . . .
C20 C 0.4872(14) 0.6296(6) 0.5899(6) 0.095(3) Uani 1 1 d . U . . .
H20A H 0.610641 0.653516 0.564014 0.142 Uiso 1 1 calc R U . . .
H20B H 0.393632 0.655549 0.538787 0.142 Uiso 1 1 calc R U . . .
H20C H 0.448106 0.663438 0.641972 0.142 Uiso 1 1 calc R U . . .
C21 C 0.4277(18) 0.4260(9) 0.6630(7) 0.120(3) Uani 1 1 d . U . . .
C22 C 0.2029(11) 0.4894(10) 0.6710(7) 0.121(3) Uani 1 1 d . U . . .
H22A H 0.118987 0.430325 0.701582 0.181 Uiso 1 1 calc R U . . .
H22B H 0.203374 0.542717 0.709679 0.181 Uiso 1 1 calc R U . . .
H22C H 0.157768 0.531266 0.606416 0.181 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 1.955(3) . ?
Zn1 O3 1.960(3) . ?
Zn1 N4 2.025(3) 2_765 ?
Zn1 N1 2.031(3) 2_656 ?
N1 C1 1.297(5) . ?
N1 N2 1.390(5) . ?
N2 C2 1.296(5) . ?
N3 C1 1.340(5) . ?
N3 C2 1.352(5) . ?
N3 C3 1.444(5) . ?
N4 C10 1.307(5) . ?
N4 N5 1.385(5) . ?
N5 C11 1.302(5) . ?
N6 C10 1.350(5) . ?
N6 C11 1.362(5) . ?
N6 C12 1.447(5) . ?
N7 C21 1.107(11) . ?
N7 C20 1.426(10) . ?
N7 C19 1.738(12) . ?
O1 C9 1.276(5) . ?
O2 C9 1.230(5) . ?
O3 C18 1.278(5) . ?
O4 C18 1.236(5) . ?
O5 C21 1.188(11) . ?
C1 H1A 0.9300 . ?
C2 H2A 0.9300 . ?
C3 C8 1.374(6) . ?
C3 C4 1.383(6) . ?
C4 C5 1.399(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.384(6) . ?
C5 C9 1.509(6) . ?
C6 C7 1.382(7) . ?
C6 H6A 0.9300 . ?
C7 C8 1.382(6) . ?
C7 H7A 0.9300 . ?
C8 H8A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 C17 1.373(6) . ?
C12 C13 1.385(6) . ?
C13 C14 1.398(5) . ?
C13 H13A 0.9300 . ?
C14 C15 1.379(6) . ?
C14 C18 1.500(6) . ?
C15 C16 1.376(6) . ?
C15 H15A 0.9300 . ?
C16 C17 1.396(6) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.678(14) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 O3 112.05(14) . . ?
O1 Zn1 N4 122.79(14) . 2_765 ?
O3 Zn1 N4 95.30(13) . 2_765 ?
O1 Zn1 N1 94.72(13) . 2_656 ?
O3 Zn1 N1 123.50(14) . 2_656 ?
N4 Zn1 N1 110.87(13) 2_765 2_656 ?
C1 N1 N2 107.9(3) . . ?
C1 N1 Zn1 121.4(3) . 2_656 ?
N2 N1 Zn1 128.8(3) . 2_656 ?
C2 N2 N1 105.1(3) . . ?
C1 N3 C2 104.3(3) . . ?
C1 N3 C3 128.0(3) . . ?
C2 N3 C3 127.6(3) . . ?
C10 N4 N5 108.5(3) . . ?
C10 N4 Zn1 120.7(3) . 2_765 ?
N5 N4 Zn1 129.1(2) . 2_765 ?
C11 N5 N4 105.7(3) . . ?
C10 N6 C11 105.0(3) . . ?
C10 N6 C12 125.9(3) . . ?
C11 N6 C12 129.1(3) . . ?
C21 N7 C20 147.9(12) . . ?
C21 N7 C19 99.0(10) . . ?
C20 N7 C19 113.0(8) . . ?
C9 O1 Zn1 114.0(3) . . ?
C18 O3 Zn1 113.3(3) . . ?
N1 C1 N3 110.6(4) . . ?
N1 C1 H1A 124.7 . . ?
N3 C1 H1A 124.7 . . ?
N2 C2 N3 112.1(4) . . ?
N2 C2 H2A 123.9 . . ?
N3 C2 H2A 123.9 . . ?
C8 C3 C4 121.7(4) . . ?
C8 C3 N3 119.9(4) . . ?
C4 C3 N3 118.4(4) . . ?
C3 C4 C5 118.9(4) . . ?
C3 C4 H4A 120.5 . . ?
C5 C4 H4A 120.5 . . ?
C6 C5 C4 119.0(4) . . ?
C6 C5 C9 120.4(4) . . ?
C4 C5 C9 120.6(4) . . ?
C7 C6 C5 121.4(4) . . ?
C7 C6 H6A 119.3 . . ?
C5 C6 H6A 119.3 . . ?
C6 C7 C8 119.5(4) . . ?
C6 C7 H7A 120.3 . . ?
C8 C7 H7A 120.3 . . ?
C3 C8 C7 119.5(4) . . ?
C3 C8 H8A 120.3 . . ?
C7 C8 H8A 120.3 . . ?
O2 C9 O1 124.6(4) . . ?
O2 C9 C5 119.4(4) . . ?
O1 C9 C5 115.9(4) . . ?
N4 C10 N6 109.5(4) . . ?
N4 C10 H10A 125.2 . . ?
N6 C10 H10A 125.2 . . ?
N5 C11 N6 111.3(4) . . ?
N5 C11 H11A 124.4 . . ?
N6 C11 H11A 124.4 . . ?
C17 C12 C13 121.8(4) . . ?
C17 C12 N6 119.7(4) . . ?
C13 C12 N6 118.5(3) . . ?
C12 C13 C14 119.4(4) . . ?
C12 C13 H13A 120.3 . . ?
C14 C13 H13A 120.3 . . ?
C15 C14 C13 118.9(4) . . ?
C15 C14 C18 120.4(4) . . ?
C13 C14 C18 120.6(4) . . ?
C16 C15 C14 121.1(4) . . ?
C16 C15 H15A 119.5 . . ?
C14 C15 H15A 119.5 . . ?
C15 C16 C17 120.5(4) . . ?
C15 C16 H16A 119.8 . . ?
C17 C16 H16A 119.8 . . ?
C12 C17 C16 118.3(4) . . ?
C12 C17 H17A 120.8 . . ?
C16 C17 H17A 120.8 . . ?
O4 C18 O3 124.2(4) . . ?
O4 C18 C14 119.2(4) . . ?
O3 C18 C14 116.6(4) . . ?
N7 C19 H19A 109.5 . . ?
N7 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N7 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N7 C20 H20A 109.5 . . ?
N7 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N7 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N7 C21 O5 141.7(15) . . ?
N7 C21 C22 99.2(10) . . ?
O5 C21 C22 119.1(10) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_refine_diff_density_max         1.803
_refine_diff_density_min         -0.783
_refine_diff_density_rms         0.097

####################################################################### 
# 
# 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-beta
_database_code_depnum_ccdc_archive 'CCDC 2160143'
loop_
_audit_author_name
_audit_author_address
'Ai-Xin Zhu'
;Yunnan Normal University
China
;
_audit_update_record             
;
2022-03-19 deposited with the CCDC.	2022-06-23 downloaded from the CCDC.
;
# start Validation Reply Form: Two Alert B issues

_vrf_THETM01_1-beta              
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
Calculated sin(theta_max)/wavelength = 0.5617

RESPONSE: Because of  overall low crystal quality at high two-theta degrees,
2theta was cut-off at 120 degrees. These crystals diffracted very weakly 
and no significant diffraction was observed above this level.
;

_vrf_PLAT341_1-beta              
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............0.01829 Ang

RESPONSE: Because the crystal was obtained by the removal of DMA
 by heating,  the large associated su's on the C-C bonds,
 and many of the light atom angles, is the expected result of the 
weakly  diffracting data-set.
;

# end Validation Reply Form 
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H12 N6 O4 Zn'
_chemical_formula_weight         441.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.5102(9)
_cell_length_b                   7.7166(12)
_cell_length_c                   17.682(3)
_cell_angle_alpha                102.090(9)
_cell_angle_beta                 91.927(12)
_cell_angle_gamma                100.163(9)
_cell_volume                     852.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    302(2)
_cell_measurement_reflns_used    6899
_cell_measurement_theta_min      2.562
_cell_measurement_theta_max      71.064

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.720
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    2.386
_shelx_estimated_absorpt_T_min   0.634
_shelx_estimated_absorpt_T_max   0.701
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2903
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1747 before and 0.1149 after correction.
The Ratio of minimum to maximum transmission is 0.3854.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      302(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11143
_diffrn_reflns_av_unetI/netI     0.0742
_diffrn_reflns_av_R_equivalents  0.0993
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.562
_diffrn_reflns_theta_max         59.992
_diffrn_reflns_theta_full        59.993
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             2451
_reflns_number_gt                1826
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1334P)²+10.1078P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2451
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1447
_refine_ls_R_factor_gt           0.1173
_refine_ls_wR_factor_ref         0.3149
_refine_ls_wR_factor_gt          0.3007
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.7511(3) 0.5154(2) 0.73766(9) 0.0700(7) Uani 1 1 d . . . . .
O1 O 0.6934(15) 0.3955(13) 0.6302(5) 0.079(3) Uani 1 1 d . . . . .
O2 O 0.3541(16) 0.3273(15) 0.6496(5) 0.089(3) Uani 1 1 d . . . . .
O3 O 0.8942(14) 0.3976(13) 0.8086(5) 0.076(2) Uani 1 1 d . . . . .
O4 O 0.5751(16) 0.2798(12) 0.8354(5) 0.079(3) Uani 1 1 d . . . . .
N1 N 1.0011(16) 0.2977(15) 0.2821(6) 0.066(3) Uani 1 1 d . . . . .
N2 N 0.9470(17) 0.1176(16) 0.2490(6) 0.073(3) Uani 1 1 d . . . . .
N3 N 0.7407(16) 0.1858(14) 0.3423(5) 0.065(3) Uani 1 1 d . . . . .
N4 N 0.4473(16) 0.3453(14) 1.2008(6) 0.066(3) Uani 1 1 d . . . . .
N5 N 0.4071(18) 0.1613(15) 1.1842(6) 0.071(3) Uani 1 1 d . . . . .
N6 N 0.6642(15) 0.2602(13) 1.1164(5) 0.059(2) Uani 1 1 d . . . . .
C1 C 0.876(2) 0.3330(18) 0.3373(7) 0.067(3) Uani 1 1 d . . . . .
H1A H 0.881652 0.446422 0.369009 0.081 Uiso 1 1 calc R U . . .
C2 C 0.792(2) 0.0583(18) 0.2867(8) 0.070(3) Uani 1 1 d . . . . .
H2A H 0.723334 -0.061512 0.276049 0.084 Uiso 1 1 calc R U . . .
C3 C 0.5757(18) 0.1784(17) 0.3949(7) 0.060(3) Uani 1 1 d . . . . .
C4 C 0.6206(19) 0.2556(17) 0.4721(7) 0.063(3) Uani 1 1 d . . . . .
H4A H 0.756034 0.313355 0.490796 0.075 Uiso 1 1 calc R U . . .
C5 C 0.4623(19) 0.2462(17) 0.5217(7) 0.063(3) Uani 1 1 d . . . . .
C6 C 0.260(2) 0.1535(19) 0.4932(7) 0.071(3) Uani 1 1 d . . . . .
H6A H 0.151187 0.148171 0.525972 0.086 Uiso 1 1 calc R U . . .
C7 C 0.225(2) 0.070(2) 0.4156(8) 0.076(4) Uani 1 1 d . . . . .
H7A H 0.092403 0.005902 0.396744 0.091 Uiso 1 1 calc R U . . .
C8 C 0.381(2) 0.081(2) 0.3654(8) 0.080(4) Uani 1 1 d . . . . .
H8A H 0.356446 0.023413 0.313272 0.095 Uiso 1 1 calc R U . . .
C9 C 0.502(2) 0.3247(17) 0.6070(8) 0.064(3) Uani 1 1 d . . . . .
C10 C 0.600(2) 0.3963(19) 1.1600(8) 0.075(4) Uani 1 1 d . . . . .
H10A H 0.657731 0.516425 1.161719 0.090 Uiso 1 1 calc R U . . .
C11 C 0.541(2) 0.1130(17) 1.1335(8) 0.070(3) Uani 1 1 d . . . . .
H11A H 0.551047 -0.005859 1.112149 0.084 Uiso 1 1 calc R U . . .
C12 C 0.8047(19) 0.2576(16) 1.0556(7) 0.062(3) Uani 1 1 d . . . . .
C13 C 0.7308(19) 0.2932(17) 0.9867(7) 0.061(3) Uani 1 1 d . . . . .
H13A H 0.598373 0.321173 0.982200 0.073 Uiso 1 1 calc R U . . .
C14 C 0.856(2) 0.2864(17) 0.9254(7) 0.065(3) Uani 1 1 d . . . . .
C15 C 1.054(2) 0.2492(17) 0.9333(7) 0.067(3) Uani 1 1 d . . . . .
H15A H 1.141099 0.248061 0.892609 0.081 Uiso 1 1 calc R U . . .
C16 C 1.122(2) 0.2135(19) 1.0028(8) 0.076(4) Uani 1 1 d . . . . .
H16A H 1.253958 0.185258 1.007555 0.092 Uiso 1 1 calc R U . . .
C17 C 0.999(2) 0.2185(17) 1.0647(7) 0.064(3) Uani 1 1 d . . . . .
H17A H 1.047336 0.196027 1.111165 0.076 Uiso 1 1 calc R U . . .
C18 C 0.766(2) 0.3268(19) 0.8493(8) 0.070(3) 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 O1 1.924(9) . ?
Zn1 O3 1.991(9) . ?
Zn1 N4 2.025(10) 2_667 ?
Zn1 N1 2.058(10) 2_766 ?
O1 C9 1.282(15) . ?
O2 C9 1.245(14) . ?
O3 C18 1.247(15) . ?
O4 C18 1.234(15) . ?
N1 C1 1.306(15) . ?
N1 N2 1.368(15) . ?
N2 C2 1.297(15) . ?
N3 C1 1.331(16) . ?
N3 C2 1.334(16) . ?
N3 C3 1.446(14) . ?
N4 C10 1.302(15) . ?
N4 N5 1.364(14) . ?
N5 C11 1.317(16) . ?
N6 C10 1.307(16) . ?
N6 C11 1.364(16) . ?
N6 C12 1.434(14) . ?
C1 H1A 0.9300 . ?
C2 H2A 0.9300 . ?
C3 C4 1.369(16) . ?
C3 C8 1.378(18) . ?
C4 C5 1.377(16) . ?
C4 H4A 0.9300 . ?
C5 C6 1.406(17) . ?
C5 C9 1.498(17) . ?
C6 C7 1.379(18) . ?
C6 H6A 0.9300 . ?
C7 C8 1.374(18) . ?
C7 H7A 0.9300 . ?
C8 H8A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 C17 1.365(17) . ?
C12 C13 1.392(17) . ?
C13 C14 1.377(16) . ?
C13 H13A 0.9300 . ?
C14 C15 1.377(18) . ?
C14 C18 1.561(18) . ?
C15 C16 1.389(18) . ?
C15 H15A 0.9300 . ?
C16 C17 1.373(17) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 O3 118.8(4) . . ?
O1 Zn1 N4 123.4(4) . 2_667 ?
O3 Zn1 N4 108.1(4) . 2_667 ?
O1 Zn1 N1 94.5(4) . 2_766 ?
O3 Zn1 N1 100.2(4) . 2_766 ?
N4 Zn1 N1 107.0(4) 2_667 2_766 ?
C9 O1 Zn1 117.3(8) . . ?
C18 O3 Zn1 110.6(9) . . ?
C1 N1 N2 107.3(10) . . ?
C1 N1 Zn1 123.1(9) . 2_766 ?
N2 N1 Zn1 129.2(8) . 2_766 ?
C2 N2 N1 104.7(10) . . ?
C1 N3 C2 103.1(10) . . ?
C1 N3 C3 125.8(11) . . ?
C2 N3 C3 131.0(11) . . ?
C10 N4 N5 107.3(10) . . ?
C10 N4 Zn1 131.3(9) . 2_667 ?
N5 N4 Zn1 120.3(8) . 2_667 ?
C11 N5 N4 105.4(10) . . ?
C10 N6 C11 103.7(10) . . ?
C10 N6 C12 129.8(11) . . ?
C11 N6 C12 125.9(10) . . ?
N1 C1 N3 111.4(11) . . ?
N1 C1 H1A 124.3 . . ?
N3 C1 H1A 124.3 . . ?
N2 C2 N3 113.4(12) . . ?
N2 C2 H2A 123.3 . . ?
N3 C2 H2A 123.3 . . ?
C4 C3 C8 122.6(11) . . ?
C4 C3 N3 119.6(10) . . ?
C8 C3 N3 117.6(11) . . ?
C3 C4 C5 119.0(11) . . ?
C3 C4 H4A 120.5 . . ?
C5 C4 H4A 120.5 . . ?
C4 C5 C6 119.9(11) . . ?
C4 C5 C9 121.5(11) . . ?
C6 C5 C9 118.4(11) . . ?
C7 C6 C5 118.7(12) . . ?
C7 C6 H6A 120.6 . . ?
C5 C6 H6A 120.6 . . ?
C8 C7 C6 121.8(12) . . ?
C8 C7 H7A 119.1 . . ?
C6 C7 H7A 119.1 . . ?
C7 C8 C3 117.7(12) . . ?
C7 C8 H8A 121.1 . . ?
C3 C8 H8A 121.1 . . ?
O2 C9 O1 124.3(12) . . ?
O2 C9 C5 120.2(12) . . ?
O1 C9 C5 115.4(10) . . ?
N4 C10 N6 112.6(12) . . ?
N4 C10 H10A 123.7 . . ?
N6 C10 H10A 123.7 . . ?
N5 C11 N6 111.1(11) . . ?
N5 C11 H11A 124.4 . . ?
N6 C11 H11A 124.4 . . ?
C17 C12 C13 122.0(11) . . ?
C17 C12 N6 121.4(11) . . ?
C13 C12 N6 116.6(11) . . ?
C14 C13 C12 119.2(12) . . ?
C14 C13 H13A 120.4 . . ?
C12 C13 H13A 120.4 . . ?
C15 C14 C13 120.0(12) . . ?
C15 C14 C18 122.7(11) . . ?
C13 C14 C18 117.3(12) . . ?
C14 C15 C16 119.1(12) . . ?
C14 C15 H15A 120.5 . . ?
C16 C15 H15A 120.5 . . ?
C17 C16 C15 122.0(13) . . ?
C17 C16 H16A 119.0 . . ?
C15 C16 H16A 119.0 . . ?
C12 C17 C16 117.7(12) . . ?
C12 C17 H17A 121.2 . . ?
C16 C17 H17A 121.2 . . ?
O4 C18 O3 127.4(13) . . ?
O4 C18 C14 115.5(12) . . ?
O3 C18 C14 117.1(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 C2 0.4(14) . . . . ?
Zn1 N1 N2 C2 173.9(9) 2_766 . . . ?
C10 N4 N5 C11 0.0(14) . . . . ?
Zn1 N4 N5 C11 169.5(9) 2_667 . . . ?
N2 N1 C1 N3 -0.5(15) . . . . ?
Zn1 N1 C1 N3 -174.5(8) 2_766 . . . ?
C2 N3 C1 N1 0.4(14) . . . . ?
C3 N3 C1 N1 -177.4(11) . . . . ?
N1 N2 C2 N3 -0.2(15) . . . . ?
C1 N3 C2 N2 -0.1(15) . . . . ?
C3 N3 C2 N2 177.6(11) . . . . ?
C1 N3 C3 C4 -49.5(17) . . . . ?
C2 N3 C3 C4 133.4(14) . . . . ?
C1 N3 C3 C8 135.5(14) . . . . ?
C2 N3 C3 C8 -41.7(19) . . . . ?
C8 C3 C4 C5 -5(2) . . . . ?
N3 C3 C4 C5 -179.5(11) . . . . ?
C3 C4 C5 C6 2.0(19) . . . . ?
C3 C4 C5 C9 178.8(11) . . . . ?
C4 C5 C6 C7 1(2) . . . . ?
C9 C5 C6 C7 -175.7(12) . . . . ?
C5 C6 C7 C8 -2(2) . . . . ?
C6 C7 C8 C3 0(2) . . . . ?
C4 C3 C8 C7 4(2) . . . . ?
N3 C3 C8 C7 178.8(12) . . . . ?
Zn1 O1 C9 O2 -0.8(17) . . . . ?
Zn1 O1 C9 C5 175.2(8) . . . . ?
C4 C5 C9 O2 174.3(12) . . . . ?
C6 C5 C9 O2 -9.0(19) . . . . ?
C4 C5 C9 O1 -1.9(18) . . . . ?
C6 C5 C9 O1 174.9(12) . . . . ?
N5 N4 C10 N6 0.8(16) . . . . ?
Zn1 N4 C10 N6 -167.1(9) 2_667 . . . ?
C11 N6 C10 N4 -1.2(15) . . . . ?
C12 N6 C10 N4 169.7(12) . . . . ?
N4 N5 C11 N6 -0.8(15) . . . . ?
C10 N6 C11 N5 1.2(15) . . . . ?
C12 N6 C11 N5 -170.2(11) . . . . ?
C10 N6 C12 C17 110.0(16) . . . . ?
C11 N6 C12 C17 -80.8(16) . . . . ?
C10 N6 C12 C13 -71.3(18) . . . . ?
C11 N6 C12 C13 97.9(15) . . . . ?
C17 C12 C13 C14 0.9(19) . . . . ?
N6 C12 C13 C14 -177.8(11) . . . . ?
C12 C13 C14 C15 -1.6(19) . . . . ?
C12 C13 C14 C18 179.8(12) . . . . ?
C13 C14 C15 C16 2.0(19) . . . . ?
C18 C14 C15 C16 -179.5(12) . . . . ?
C14 C15 C16 C17 -2(2) . . . . ?
C13 C12 C17 C16 -0.6(19) . . . . ?
N6 C12 C17 C16 178.1(12) . . . . ?
C15 C16 C17 C12 1(2) . . . . ?
Zn1 O3 C18 O4 22.1(18) . . . . ?
Zn1 O3 C18 C14 -160.0(9) . . . . ?
C15 C14 C18 O4 149.0(13) . . . . ?
C13 C14 C18 O4 -32.5(17) . . . . ?
C15 C14 C18 O3 -29.2(19) . . . . ?
C13 C14 C18 O3 149.3(12) . . . . ?

_refine_diff_density_max         0.970
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.151

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2160144'
loop_
_audit_author_name
_audit_author_address
'Ai-Xin Zhu'
;Yunnan Normal University
China
;
_audit_update_record             
;
2022-03-19 deposited with the CCDC.	2022-06-23 downloaded from the CCDC.
;
# start Validation Reply Form: Three Alert B issues

_vrf_THETM01_2                   
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
Calculated sin(theta_max)/wavelength = 0.5613

RESPONSE: Because the crystal was obtained by two-step, single-crystal 
to single-crystal transformations and  the overall crystal quality is low at high
 two-theta degrees, these crystals diffracted very weakly and no significant 
diffraction was observed above this level. Thus, 2theta was cut-off at 120 degrees. 
;

_vrf_PLAT029_2                   
;
PROBLEM: diffrn_measured_fraction_theta_full value Low .      0.947 

RESPONSE: The crystal was obtained by two-step single-crystal 
to single-crystal transformations, and the overall crystal quality is low. 
Additionally, the shape of crystal is plate. Thus, no diffraction peaks
are observed  in some areas.
;

_vrf_PLAT341_2                   
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............0.01786 Ang

RESPONSE: Because the crystal was obtained by two-step single-crystal 
to single-crystal transformations and the overall crystal quality is low the
 large associated su's on the C-C bonds, and many of the light atom angles,
 is the expected result of the weakly diffracting data-set.
;

# end Validation Reply Form 
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 N6 O6 Zn'
_chemical_formula_weight         477.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.3098(10)
_cell_length_b                   7.1905(12)
_cell_length_c                   20.346(3)
_cell_angle_alpha                98.586(9)
_cell_angle_beta                 94.474(8)
_cell_angle_gamma                91.396(9)
_cell_volume                     909.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    9182
_cell_measurement_theta_min      2.204
_cell_measurement_theta_max      67.135

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.745
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.371
_shelx_estimated_absorpt_T_min   0.661
_shelx_estimated_absorpt_T_max   0.797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4467
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1691 before and 0.1096 after correction.
The Ratio of minimum to maximum transmission is 0.5934.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13605
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_av_R_equivalents  0.0748
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.204
_diffrn_reflns_theta_max         59.931
_diffrn_reflns_theta_full        59.931
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measured_fraction_theta_full 0.947
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_Laue_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_point_group_measured_fraction_full 0.947
_reflns_number_total             2544
_reflns_number_gt                2222
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0724P)²+15.0969P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2544
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1271
_refine_ls_R_factor_gt           0.1156
_refine_ls_wR_factor_ref         0.2862
_refine_ls_wR_factor_gt          0.2807
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.7580(3) 0.5773(3) 0.27618(9) 0.0691(7) Uani 1 1 d . . . . .
N1 N 1.0853(17) 0.6646(16) 0.6833(5) 0.067(3) Uani 1 1 d . . . . .
N2 N 1.0475(16) 0.8451(16) 0.7097(6) 0.071(3) Uani 1 1 d . . . . .
N3 N 0.8176(16) 0.7597(15) 0.6241(5) 0.065(3) Uani 1 1 d . . . . .
N4 N 0.5403(16) 0.4050(17) 0.2155(5) 0.068(3) Uani 1 1 d . . . . .
N5 N 0.4908(17) 0.2305(17) 0.2297(6) 0.074(3) Uani 1 1 d . . . . .
N6 N 0.2870(15) 0.2874(17) 0.1437(5) 0.068(3) Uani 1 1 d . . . . .
C1 C 0.9421(19) 0.6189(17) 0.6313(6) 0.061(3) Uani 1 1 d . . . . .
H1A H 0.931576 0.502953 0.603801 0.074 Uiso 1 1 calc R U . . .
C2 C 0.888(2) 0.898(2) 0.6735(7) 0.077(4) Uani 1 1 d . . . . .
H2A H 0.830110 1.016289 0.680726 0.092 Uiso 1 1 calc R U . . .
C3 C 0.6433(19) 0.7713(17) 0.5744(6) 0.059(3) Uani 1 1 d . . . . .
C4 C 0.6743(19) 0.7244(17) 0.5082(6) 0.059(3) Uani 1 1 d . . . . .
H4A H 0.806430 0.685553 0.495360 0.071 Uiso 1 1 calc R U . . .
C5 C 0.5055(19) 0.7352(19) 0.4600(6) 0.063(3) Uani 1 1 d . . . . .
C6 C 0.3145(19) 0.7944(17) 0.4810(6) 0.062(3) Uani 1 1 d . . . . .
H6A H 0.201717 0.802868 0.449428 0.074 Uiso 1 1 calc R U . . .
C7 C 0.285(2) 0.842(2) 0.5471(7) 0.069(4) Uani 1 1 d . . . . .
H7A H 0.153893 0.883271 0.560153 0.083 Uiso 1 1 calc R U . . .
C8 C 0.452(2) 0.827(2) 0.5948(7) 0.069(4) Uani 1 1 d . . . . .
H8A H 0.432677 0.854559 0.640037 0.083 Uiso 1 1 calc R U . . .
C9 C 0.536(2) 0.694(2) 0.3869(7) 0.070(4) Uani 1 1 d . . . . .
C10 C 0.420(2) 0.4392(17) 0.1638(6) 0.063(3) Uani 1 1 d . . . . .
H10A H 0.423980 0.548253 0.144424 0.076 Uiso 1 1 calc R U . . .
C11 C 0.335(2) 0.1650(19) 0.1857(7) 0.071(4) Uani 1 1 d . . . . .
H11A H 0.266867 0.048090 0.183685 0.085 Uiso 1 1 calc R U . . .
C12 C 0.1184(18) 0.2652(15) 0.0901(6) 0.052(3) Uani 1 1 d . . . . .
C13 C 0.1661(19) 0.2824(18) 0.0273(6) 0.065(3) Uani 1 1 d . . . . .
H13A H 0.304397 0.313202 0.018872 0.078 Uiso 1 1 calc R U . . .
C14 C 0.003(2) 0.2530(18) -0.0250(6) 0.063(3) Uani 1 1 d . . . . .
C15 C -0.198(2) 0.209(2) -0.0104(7) 0.073(4) Uani 1 1 d . . . . .
H15A H -0.307916 0.196430 -0.044092 0.088 Uiso 1 1 calc R U . . .
C16 C -0.242(2) 0.183(2) 0.0523(7) 0.082(4) Uani 1 1 d . . . . .
H16A H -0.378629 0.145289 0.060334 0.098 Uiso 1 1 calc R U . . .
C17 C -0.083(2) 0.212(2) 0.1036(7) 0.070(4) Uani 1 1 d . . . . .
H17A H -0.111538 0.195344 0.146647 0.084 Uiso 1 1 calc R U . . .
C18 C 0.055(2) 0.2635(19) -0.0950(7) 0.067(3) Uani 1 1 d . . . . .
O1 O 0.7256(15) 0.6778(15) 0.3712(4) 0.077(3) Uani 1 1 d . . . . .
O1W O 1.0490(14) 0.6359(16) 0.2489(5) 0.090(3) Uani 1 1 d . . . . .
H1WA H 1.077793 0.656645 0.210486 0.108 Uiso 1 1 d R U . . .
H1WB H 1.151133 0.648765 0.279266 0.108 Uiso 1 1 d R U . . .
O2 O 0.3765(15) 0.6795(15) 0.3470(5) 0.082(3) Uani 1 1 d . . . . .
O2W O 0.6538(14) 0.8046(13) 0.2296(4) 0.076(3) Uani 1 1 d . . . . .
H2WA H 0.687634 0.921316 0.234576 0.091 Uiso 1 1 d R U . . .
H2WB H 0.694814 0.786986 0.190366 0.091 Uiso 1 1 d R U . . .
O3 O 0.2457(15) 0.2798(16) -0.1061(5) 0.087(3) Uani 1 1 d . . . . .
O4 O -0.0980(15) 0.2440(15) -0.1399(4) 0.081(3) 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 O1 1.988(9) . ?
Zn1 O1W 2.012(9) . ?
Zn1 N4 2.035(10) . ?
Zn1 O2W 2.102(9) . ?
Zn1 N1 2.251(10) 2_766 ?
N1 C1 1.333(15) . ?
N1 N2 1.363(15) . ?
N2 C2 1.299(17) . ?
N3 C1 1.315(15) . ?
N3 C2 1.344(16) . ?
N3 C3 1.448(15) . ?
N4 C10 1.307(15) . ?
N4 N5 1.363(15) . ?
N5 C11 1.303(15) . ?
N6 C11 1.339(16) . ?
N6 C10 1.352(15) . ?
N6 C12 1.451(14) . ?
C1 H1A 0.9300 . ?
C2 H2A 0.9300 . ?
C3 C8 1.358(17) . ?
C3 C4 1.367(17) . ?
C4 C5 1.403(16) . ?
C4 H4A 0.9300 . ?
C5 C6 1.367(17) . ?
C5 C9 1.500(18) . ?
C6 C7 1.365(18) . ?
C6 H6A 0.9300 . ?
C7 C8 1.395(17) . ?
C7 H7A 0.9300 . ?
C8 H8A 0.9300 . ?
C9 O2 1.232(15) . ?
C9 O1 1.268(15) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 C13 1.358(17) . ?
C12 C17 1.381(17) . ?
C13 C14 1.410(16) . ?
C13 H13A 0.9300 . ?
C14 C15 1.363(18) . ?
C14 C18 1.499(18) . ?
C15 C16 1.366(18) . ?
C15 H15A 0.9300 . ?
C16 C17 1.378(17) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 O3 1.247(15) . ?
C18 O4 1.268(14) . ?
O1W H1WA 0.8500 . ?
O1W H1WB 0.8501 . ?
O2W H2WA 0.8500 . ?
O2W H2WB 0.8501 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 O1W 112.3(4) . . ?
O1 Zn1 N4 124.7(4) . . ?
O1W Zn1 N4 122.5(4) . . ?
O1 Zn1 O2W 100.8(4) . . ?
O1W Zn1 O2W 86.7(4) . . ?
N4 Zn1 O2W 89.4(4) . . ?
O1 Zn1 N1 85.0(4) . 2_766 ?
O1W Zn1 N1 84.6(4) . 2_766 ?
N4 Zn1 N1 92.9(4) . 2_766 ?
O2W Zn1 N1 170.9(4) . 2_766 ?
C1 N1 N2 106.1(10) . . ?
C1 N1 Zn1 116.1(9) . 2_766 ?
N2 N1 Zn1 134.2(8) . 2_766 ?
C2 N2 N1 106.8(11) . . ?
C1 N3 C2 104.9(11) . . ?
C1 N3 C3 129.3(11) . . ?
C2 N3 C3 125.8(11) . . ?
C10 N4 N5 110.0(10) . . ?
C10 N4 Zn1 129.5(9) . . ?
N5 N4 Zn1 120.3(7) . . ?
C11 N5 N4 105.0(10) . . ?
C11 N6 C10 105.9(10) . . ?
C11 N6 C12 126.8(11) . . ?
C10 N6 C12 127.2(11) . . ?
N3 C1 N1 111.0(11) . . ?
N3 C1 H1A 124.5 . . ?
N1 C1 H1A 124.5 . . ?
N2 C2 N3 111.2(13) . . ?
N2 C2 H2A 124.4 . . ?
N3 C2 H2A 124.4 . . ?
C8 C3 C4 121.7(12) . . ?
C8 C3 N3 118.8(12) . . ?
C4 C3 N3 119.5(11) . . ?
C3 C4 C5 119.6(12) . . ?
C3 C4 H4A 120.2 . . ?
C5 C4 H4A 120.2 . . ?
C6 C5 C4 118.4(12) . . ?
C6 C5 C9 120.3(11) . . ?
C4 C5 C9 121.2(12) . . ?
C7 C6 C5 121.8(12) . . ?
C7 C6 H6A 119.1 . . ?
C5 C6 H6A 119.1 . . ?
C6 C7 C8 119.5(12) . . ?
C6 C7 H7A 120.2 . . ?
C8 C7 H7A 120.2 . . ?
C3 C8 C7 119.1(13) . . ?
C3 C8 H8A 120.5 . . ?
C7 C8 H8A 120.5 . . ?
O2 C9 O1 125.2(13) . . ?
O2 C9 C5 118.3(12) . . ?
O1 C9 C5 116.5(11) . . ?
N4 C10 N6 107.6(11) . . ?
N4 C10 H10A 126.2 . . ?
N6 C10 H10A 126.2 . . ?
N5 C11 N6 111.4(12) . . ?
N5 C11 H11A 124.3 . . ?
N6 C11 H11A 124.3 . . ?
C13 C12 C17 121.8(11) . . ?
C13 C12 N6 119.4(11) . . ?
C17 C12 N6 118.6(11) . . ?
C12 C13 C14 119.0(12) . . ?
C12 C13 H13A 120.5 . . ?
C14 C13 H13A 120.5 . . ?
C15 C14 C13 118.6(12) . . ?
C15 C14 C18 121.9(11) . . ?
C13 C14 C18 119.5(12) . . ?
C14 C15 C16 121.9(12) . . ?
C14 C15 H15A 119.0 . . ?
C16 C15 H15A 119.0 . . ?
C15 C16 C17 119.7(13) . . ?
C15 C16 H16A 120.2 . . ?
C17 C16 H16A 120.2 . . ?
C16 C17 C12 118.9(13) . . ?
C16 C17 H17A 120.6 . . ?
C12 C17 H17A 120.6 . . ?
O3 C18 O4 124.0(13) . . ?
O3 C18 C14 118.6(11) . . ?
O4 C18 C14 117.3(12) . . ?
C9 O1 Zn1 115.5(8) . . ?
Zn1 O1W H1WA 125.9 . . ?
Zn1 O1W H1WB 117.0 . . ?
H1WA O1W H1WB 116.9 . . ?
Zn1 O2W H2WA 134.6 . . ?
Zn1 O2W H2WB 107.0 . . ?
H2WA O2W H2WB 91.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 C2 0.0(15) . . . . ?
Zn1 N1 N2 C2 -156.7(10) 2_766 . . . ?
C10 N4 N5 C11 -1.1(16) . . . . ?
Zn1 N4 N5 C11 174.3(9) . . . . ?
C2 N3 C1 N1 0.4(15) . . . . ?
C3 N3 C1 N1 179.5(12) . . . . ?
N2 N1 C1 N3 -0.2(15) . . . . ?
Zn1 N1 C1 N3 161.3(8) 2_766 . . . ?
N1 N2 C2 N3 0.3(16) . . . . ?
C1 N3 C2 N2 -0.4(16) . . . . ?
C3 N3 C2 N2 -179.6(12) . . . . ?
C1 N3 C3 C8 127.8(15) . . . . ?
C2 N3 C3 C8 -53.2(18) . . . . ?
C1 N3 C3 C4 -51.5(18) . . . . ?
C2 N3 C3 C4 127.5(14) . . . . ?
C8 C3 C4 C5 0.6(19) . . . . ?
N3 C3 C4 C5 179.9(11) . . . . ?
C3 C4 C5 C6 0.6(18) . . . . ?
C3 C4 C5 C9 177.1(12) . . . . ?
C4 C5 C6 C7 -0.4(19) . . . . ?
C9 C5 C6 C7 -176.9(12) . . . . ?
C5 C6 C7 C8 -1(2) . . . . ?
C4 C3 C8 C7 -2(2) . . . . ?
N3 C3 C8 C7 178.8(12) . . . . ?
C6 C7 C8 C3 2(2) . . . . ?
C6 C5 C9 O2 -14(2) . . . . ?
C4 C5 C9 O2 170.0(13) . . . . ?
C6 C5 C9 O1 165.8(13) . . . . ?
C4 C5 C9 O1 -10.6(19) . . . . ?
N5 N4 C10 N6 0.6(15) . . . . ?
Zn1 N4 C10 N6 -174.3(9) . . . . ?
C11 N6 C10 N4 0.1(15) . . . . ?
C12 N6 C10 N4 176.9(11) . . . . ?
N4 N5 C11 N6 1.2(16) . . . . ?
C10 N6 C11 N5 -0.9(16) . . . . ?
C12 N6 C11 N5 -177.7(12) . . . . ?
C11 N6 C12 C13 -125.7(14) . . . . ?
C10 N6 C12 C13 58.1(17) . . . . ?
C11 N6 C12 C17 48.9(18) . . . . ?
C10 N6 C12 C17 -127.2(14) . . . . ?
C17 C12 C13 C14 2.9(19) . . . . ?
N6 C12 C13 C14 177.4(11) . . . . ?
C12 C13 C14 C15 0(2) . . . . ?
C12 C13 C14 C18 -177.4(12) . . . . ?
C13 C14 C15 C16 -4(2) . . . . ?
C18 C14 C15 C16 174.0(14) . . . . ?
C14 C15 C16 C17 4(2) . . . . ?
C15 C16 C17 C12 -1(2) . . . . ?
C13 C12 C17 C16 -3(2) . . . . ?
N6 C12 C17 C16 -177.3(13) . . . . ?
C15 C14 C18 O3 -170.6(14) . . . . ?
C13 C14 C18 O3 7(2) . . . . ?
C15 C14 C18 O4 5(2) . . . . ?
C13 C14 C18 O4 -177.1(12) . . . . ?
O2 C9 O1 Zn1 -11.4(19) . . . . ?
C5 C9 O1 Zn1 169.2(9) . . . . ?

_refine_diff_density_max         0.958
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.112

