# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_HNU-25
_database_code_depnum_ccdc_archive 'CCDC 1884335'
loop_
_audit_author_name
_audit_author_address
'Meiling Li'
;Hainan University
China
;
_audit_update_record             
;
2018-12-11 deposited with the CCDC.	2019-02-18 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            'C26 H17 N9 O8 Zn2'
_chemical_formula_weight         714.27

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      trigonal
_space_group_IT_number           167
_space_group_name_H-M_alt        'R -3 c :H'
_space_group_name_Hall           '-R 3 2"c'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+5/6'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+7/6'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z-1/6'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+1/6'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'

_cell_length_a                   21.5586(3)
_cell_length_b                   21.5586(3)
_cell_length_c                   62.2218(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     25044.6(9)
_cell_formula_units_Z            18
_cell_measurement_temperature    120.00(10)
_cell_measurement_reflns_used    13911
_cell_measurement_theta_min      4.1250
_cell_measurement_theta_max      71.9360

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.850
_exptl_crystal_F_000             6480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_absorpt_coefficient_mu    1.348
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.35225
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120.00(10)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18315
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -69
_diffrn_reflns_limit_l_max       74
_diffrn_reflns_theta_min         4.263
_diffrn_reflns_theta_max         74.337
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measured_fraction_theta_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_point_group_measured_fraction_full 0.964
_reflns_number_total             5324
_reflns_number_gt                3962
_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.
 
 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.
;

_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1668P)²+52.8027P] 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         5324
_refine_ls_number_parameters     205
_refine_ls_number_restraints     225
_refine_ls_R_factor_all          0.1086
_refine_ls_R_factor_gt           0.0961
_refine_ls_wR_factor_ref         0.3234
_refine_ls_wR_factor_gt          0.3077
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.127
_refine_ls_shift/su_max          0.001
_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
C1 C 0.2536(6) 0.5263(5) 0.38388(17) 0.175(3) Uani 1 1 d . U . . .
C2 C 0.2716(5) 0.5500(4) 0.36263(16) 0.162(3) Uani 1 1 d . U . . .
H2 H 0.258194 0.581461 0.356893 0.194 Uiso 1 1 calc R U . . .
C3 C 0.3084(5) 0.5273(5) 0.35036(16) 0.160(3) Uani 1 1 d . U . . .
H3 H 0.319810 0.543099 0.336243 0.192 Uiso 1 1 calc R U . . .
C4 C 0.3283(4) 0.4832(4) 0.35817(17) 0.151(3) Uani 1 1 d . U . . .
C5 C 0.3104(5) 0.4576(4) 0.37922(17) 0.166(3) Uani 1 1 d . U . . .
H5 H 0.322749 0.424778 0.384410 0.200 Uiso 1 1 calc R U . . .
C6 C 0.2744(6) 0.4808(5) 0.39232(16) 0.177(3) Uani 1 1 d . U . . .
H6 H 0.264429 0.465884 0.406554 0.212 Uiso 1 1 calc R U . . .
C7 C 0.3696(5) 0.4618(5) 0.3440(2) 0.171(4) Uani 1 1 d . U . . .
C9 C 0.2139(7) 0.5556(6) 0.3965(2) 0.222(5) Uani 1 1 d . U . . .
H9A H 0.246189 0.605991 0.399375 0.266 Uiso 1 1 calc R U . . .
H9B H 0.174834 0.551872 0.387752 0.266 Uiso 1 1 calc R U . . .
C11 C 0.1203(7) 0.4536(7) 0.416667 0.142(3) Uani 1 2 d S TU P . .
C12 C 0.0890(6) 0.4191(6) 0.43576(10) 0.140(2) Uani 1 1 d . U . . .
H12 H 0.111192 0.440263 0.448679 0.168 Uiso 1 1 calc R U . . .
C13 C 0.0264(7) 0.3551(7) 0.43619(13) 0.156(3) Uani 1 1 d . U . . .
C14 C -0.0102(7) 0.3231(7) 0.416667 0.158(4) Uani 1 2 d S TU P . .
H14 H -0.053370 0.279959 0.416666 0.189 Uiso 1 2 calc R U P . .
C15 C 0.0043(8) 0.3253(8) 0.4583(2) 0.181(4) Uani 1 1 d . U . . .
N2 N 0.5739(5) 0.4481(5) 0.3120(2) 0.216(5) Uani 1 1 d . U . . .
N5 N 0.6372(4) 0.5040(5) 0.3138(2) 0.204(5) Uani 1 1 d . U . . .
N1 N 0.5272(3) 0.4593(3) 0.32292(10) 0.1312(19) Uani 1 1 d . U . . .
C21 C 0.5664(3) 0.5159(3) 0.33346(9) 0.1189(15) Uani 1 1 d . U . . .
H21 H 0.549623 0.533423 0.342682 0.143 Uiso 1 1 calc R U . . .
N3 N 0.6353(3) 0.5456(3) 0.32902(11) 0.1302(18) Uani 1 1 d . U . . .
N4 N 0.1852(7) 0.5185(7) 0.416667 0.196(4) Uani 1 2 d S TU P . .
O1 O 0.3772(3) 0.4152(3) 0.34797(12) 0.168(2) Uani 1 1 d . U . . .
O2 O 0.3932(5) 0.4915(6) 0.32631(13) 0.218(3) Uani 1 1 d . U . . .
O3 O 0.0365(5) 0.3605(5) 0.47452(9) 0.201(3) Uani 1 1 d . U . . .
O4 O -0.0436(6) 0.2694(6) 0.45812(18) 0.245(5) Uani 1 1 d . U . . .
Zn01 Zn 0.42283(4) 0.38810(3) 0.32489(2) 0.1046(4) Uani 1 1 d . 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
C1 C6 1.371(13) . ?
C1 C2 1.401(13) . ?
C1 C9 1.511(10) . ?
C2 C3 1.358(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.314(14) . ?
C3 H3 0.9300 . ?
C4 C5 1.399(14) . ?
C4 C7 1.482(11) . ?
C5 C6 1.380(10) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.123(13) . ?
C7 O2 1.249(13) . ?
C9 N4 1.452(13) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 C12 1.385(11) 10_455 ?
C11 C12 1.385(11) . ?
C11 N4 1.398(17) . ?
C12 C13 1.366(13) . ?
C12 H12 0.9300 . ?
C13 C14 1.424(13) . ?
C13 C15 1.493(15) . ?
C14 H14 0.9300 . ?
C15 O4 1.129(15) . ?
C15 O3 1.243(16) . ?
N2 N5 1.296(11) . ?
N2 N1 1.332(8) . ?
N5 N3 1.318(9) . ?
N1 C21 1.266(7) . ?
N1 Zn01 1.995(5) . ?
C21 N3 1.320(7) . ?
C21 H21 0.8600 . ?
N3 Zn01 2.021(6) 32 ?
O1 Zn01 1.985(5) . ?
O4 Zn01 2.135(11) 34 ?

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
C6 C1 C2 119.5(7) . . ?
C6 C1 C9 123.8(9) . . ?
C2 C1 C9 116.6(10) . . ?
C3 C2 C1 120.3(10) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 120.9(10) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 120.4(7) . . ?
C3 C4 C7 118.0(11) . . ?
C5 C4 C7 121.5(10) . . ?
C6 C5 C4 120.3(9) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C1 C6 C5 118.5(9) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
O1 C7 O2 116.6(9) . . ?
O1 C7 C4 122.0(11) . . ?
O2 C7 C4 121.2(12) . . ?
N4 C9 C1 113.1(8) . . ?
N4 C9 H9A 109.0 . . ?
C1 C9 H9A 109.0 . . ?
N4 C9 H9B 109.0 . . ?
C1 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C12 C11 C12 118.4(14) 10_455 . ?
C12 C11 N4 120.8(7) 10_455 . ?
C12 C11 N4 120.8(7) . . ?
C13 C12 C11 122.0(9) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C12 C13 C14 120.1(9) . . ?
C12 C13 C15 113.2(11) . . ?
C14 C13 C15 126.7(13) . . ?
C13 C14 C13 117.5(15) 10_455 . ?
C13 C14 H14 121.3 10_455 . ?
C13 C14 H14 121.3 . . ?
O4 C15 O3 126.4(15) . . ?
O4 C15 C13 111.9(15) . . ?
O3 C15 C13 121.7(14) . . ?
N5 N2 N1 109.1(7) . . ?
N2 N5 N3 108.6(6) . . ?
C21 N1 N2 103.7(6) . . ?
C21 N1 Zn01 131.5(4) . . ?
N2 N1 Zn01 123.8(5) . . ?
N1 C21 N3 114.0(5) . . ?
N1 C21 H21 123.0 . . ?
N3 C21 H21 123.0 . . ?
N5 N3 C21 103.3(6) . . ?
N5 N3 Zn01 125.6(5) . 32 ?
C21 N3 Zn01 131.1(5) . 32 ?
C11 N4 C9 119.3(8) . . ?
C11 N4 C9 119.2(8) . 10_455 ?
C9 N4 C9 121.5(17) . 10_455 ?
C7 O1 Zn01 114.9(8) . . ?
C15 O4 Zn01 100.9(12) . 34 ?
O1 Zn01 N1 110.6(2) . . ?
O1 Zn01 N3 102.4(3) . 33_545 ?
N1 Zn01 N3 102.2(3) . 33_545 ?
O1 Zn01 O4 126.9(3) . 28 ?
N1 Zn01 O4 98.9(4) . 28 ?
N3 Zn01 O4 113.5(3) 33_545 28 ?

_refine_diff_density_max         0.771
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.071




####################################################################### 
# 
# 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_HNU-26
_database_code_depnum_ccdc_archive 'CCDC 1884348'
loop_
_audit_author_name
_audit_author_address
'Meiling Li'
;Hainan University
China
;
_audit_update_record             
;
2018-12-11 deposited with the CCDC.	2019-02-18 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            'C28 H21 N9 O8 Zn2'
_chemical_formula_weight         742.32

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      orthorhombic
_space_group_IT_number           63
_space_group_name_H-M_alt        'C m c m'
_space_group_name_Hall           '-C 2c 2'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, -z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, y, -z-1/2'
'-x, y, z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, -z-1/2'
'-x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   27.5369(9)
_cell_length_b                   24.6251(5)
_cell_length_c                   20.1958(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     13694.8(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    100.01(10)
_cell_measurement_reflns_used    8040
_cell_measurement_theta_min      2.4720
_cell_measurement_theta_max      71.9200

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.699
_exptl_crystal_F_000             2840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_absorpt_coefficient_mu    1.115
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.83781
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.9d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.01(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23641
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.407
_diffrn_reflns_theta_max         74.385
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7136
_reflns_number_gt                4504
_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.
 
 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.
;

_computing_data_collection       'CrysAlisPro 1.171.39.9d (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.9d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.9d (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] 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         7136
_refine_ls_number_parameters     222
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_gt           0.0723
_refine_ls_wR_factor_ref         0.2949
_refine_ls_wR_factor_gt          0.2650
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.115
_refine_ls_shift/su_max          0.001
_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 0.11037(2) 0.85468(2) 0.90183(3) 0.0859(3) Uani 1 1 d . . . . .
O1 O 0.11688(11) 0.79928(15) 1.0161(2) 0.1268(12) Uani 1 1 d . . . . .
O2 O 0.12280(12) 0.77619(15) 0.9116(2) 0.1120(10) Uani 1 1 d . . . . .
O3 O 0.28911(11) 0.38308(13) 0.89442(18) 0.1235(12) Uani 1 1 d . . . . .
O4 O 0.35550(8) 0.41321(9) 0.94618(16) 0.0922(8) Uani 1 1 d . . . . .
N1 N 0.03931(11) 0.86747(13) 0.9250(2) 0.0929(9) Uani 1 1 d . . . . .
N2 N 0.02355(12) 0.9024(2) 0.9693(3) 0.155(2) Uani 1 1 d . . . . .
N3 N 0.0807(3) 0.91165(19) 0.7819(2) 0.171(2) Uani 1 1 d . . . . .
N4 N 0.10920(11) 0.87052(14) 0.8043(2) 0.0982(11) Uani 1 1 d . . . . .
N5 N 0.15636(15) 0.500000 1.000000 0.126(2) Uani 1 2 d S T P . .
C1 C 0.30807(15) 0.500000 1.000000 0.0816(13) Uani 1 2 d S T P . .
H1 H 0.341847 0.500001 0.999997 0.098 Uiso 1 2 calc R U P . .
C2 C 0.12195(15) 0.7654(2) 0.9712(4) 0.1135(17) Uani 1 1 d . . . . .
C3 C 0.12469(13) 0.70470(19) 0.9888(3) 0.0999(13) Uani 1 1 d . . . . .
C4 C 0.12229(17) 0.6892(2) 1.0519(4) 0.1268(19) Uani 1 1 d . . . . .
H4 H 0.119662 0.715279 1.085065 0.152 Uiso 1 1 calc R U . . .
C5 C 0.12367(18) 0.6358(2) 1.0682(4) 0.1260(18) Uani 1 1 d . . . . .
H5 H 0.121296 0.626302 1.112693 0.151 Uiso 1 1 calc R U . . .
C6 C 0.12837(13) 0.59518(18) 1.0224(4) 0.1115(17) Uani 1 1 d . . . . .
C7 C 0.13151(17) 0.6104(2) 0.9585(4) 0.133(2) Uani 1 1 d . . . . .
H7 H 0.135068 0.584468 0.925377 0.160 Uiso 1 1 calc R U . . .
C8 C 0.12930(16) 0.6679(2) 0.9415(3) 0.1155(15) Uani 1 1 d . . . . .
H8 H 0.131138 0.678692 0.897476 0.139 Uiso 1 1 calc R U . . .
C9 C 0.12931(14) 0.53648(16) 1.0437(3) 0.127(2) Uani 1 1 d . . . . .
H91 H 0.143384 0.534456 1.087666 0.152 Uiso 1 1 calc R U . . .
H92 H 0.096112 0.523542 1.046802 0.152 Uiso 1 1 calc R U . . .
C10 C 0.20599(16) 0.500000 1.000000 0.0962(17) Uani 1 2 d S T P . .
C11 C 0.23221(12) 0.45980(13) 0.9667(2) 0.0929(12) Uani 1 1 d . . . . .
H11 H 0.215486 0.432621 0.944299 0.111 Uiso 1 1 calc R U . . .
C12 C 0.28295(12) 0.45948(12) 0.9663(2) 0.0859(10) Uani 1 1 d . . . . .
C13 C 0.30988(13) 0.41506(14) 0.9329(2) 0.0919(10) Uani 1 1 d . . . . .
C14 C 0.000000 0.8455(2) 0.9004(3) 0.099(2) Uani 1 2 d S T P . .
C15 C 0.000000 0.8031(4) 0.8457(5) 0.175(4) Uani 1 2 d S TU P . .
H15A H 0.008810 0.819888 0.804489 0.263 Uiso 0.5 1 calc R U P . .
H15B H -0.031828 0.787495 0.841839 0.263 Uiso 0.5 1 calc R U P . .
H15C H 0.023018 0.775096 0.856135 0.263 Uiso 0.5 1 calc R U P . .
C16 C 0.1229(3) 0.8462(3) 0.750000 0.117(2) Uani 1 2 d S T P . .
C17 C 0.1594(4) 0.7999(5) 0.750000 0.200(4) Uani 1 2 d S TU P . .
H17A H 0.171320 0.794279 0.794154 0.301 Uiso 0.5 1 calc R U P . .
H17B H 0.186025 0.808776 0.721278 0.301 Uiso 0.5 1 calc R U P . .
H17C H 0.143952 0.767298 0.734567 0.301 Uiso 0.5 1 calc R U P . .


_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 O4 1.940(2) 15 ?
Zn1 O2 1.973(4) . ?
Zn1 N4 2.008(4) . ?
Zn1 N1 2.036(3) . ?
O1 C2 1.240(6) . ?
O2 C2 1.232(7) . ?
O3 C13 1.245(4) . ?
O4 C13 1.286(4) . ?
N1 C14 1.308(4) . ?
N1 N2 1.316(5) . ?
N2 N2 1.297(7) 11 ?
N3 N3 1.290(10) 10_557 ?
N3 N4 1.359(6) . ?
N4 C16 1.305(5) . ?
N5 C10 1.367(6) . ?
N5 C9 1.463(5) . ?
N5 C9 1.463(5) 3_567 ?
C1 C12 1.392(4) 3_567 ?
C1 C12 1.392(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.537(7) . ?
C3 C8 1.322(7) . ?
C3 C4 1.332(8) . ?
C4 C5 1.357(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.369(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.348(8) . ?
C6 C9 1.508(6) . ?
C7 C8 1.457(7) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 H91 0.9700 . ?
C9 H92 0.9700 . ?
C10 C11 1.397(4) 3_567 ?
C10 C11 1.397(4) . ?
C11 C12 1.397(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.484(5) . ?
C14 C15 1.521(10) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C15 H15A 0.96(6) 11 ?
C15 H15B 0.96(6) 11 ?
C15 H15C 0.96(12) 11 ?
C16 C17 1.521(11) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C17 H17A 0.96(4) 10_557 ?
C17 H17B 0.96(11) 10_557 ?
C17 H17C 0.96(7) 10_557 ?

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 Zn1 O2 126.68(15) 15 . ?
O4 Zn1 N4 108.45(14) 15 . ?
O2 Zn1 N4 106.96(17) . . ?
O4 Zn1 N1 104.17(12) 15 . ?
O2 Zn1 N1 107.17(14) . . ?
N4 Zn1 N1 100.35(15) . . ?
C2 O2 Zn1 107.9(4) . . ?
C13 O4 Zn1 113.8(2) . 15_545 ?
C14 N1 N2 104.8(3) . . ?
C14 N1 Zn1 130.1(3) . . ?
N2 N1 Zn1 125.1(3) . . ?
N2 N2 N1 109.3(2) 11 . ?
N3 N3 N4 109.4(3) 10_557 . ?
C16 N4 N3 103.3(5) . . ?
C16 N4 Zn1 136.9(4) . . ?
N3 N4 Zn1 118.7(3) . . ?
C10 N5 C9 120.6(2) . . ?
C10 N5 C9 120.6(2) . 3_567 ?
C9 N5 C9 118.8(5) . 3_567 ?
C12 C1 C12 120.4(4) 3_567 . ?
C12 C1 H1 119.8 3_567 . ?
C12 C1 H1 119.8 . . ?
O2 C2 O1 124.7(6) . . ?
O2 C2 C3 115.8(5) . . ?
O1 C2 C3 119.4(7) . . ?
C8 C3 C4 120.0(5) . . ?
C8 C3 C2 120.3(6) . . ?
C4 C3 C2 119.8(5) . . ?
C3 C4 C5 120.5(6) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 123.1(7) . . ?
C4 C5 H5 118.4 . . ?
C6 C5 H5 118.4 . . ?
C7 C6 C5 116.8(5) . . ?
C7 C6 C9 122.6(6) . . ?
C5 C6 C9 120.6(6) . . ?
C6 C7 C8 119.5(6) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C3 C8 C7 120.0(6) . . ?
C3 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
N5 C9 C6 115.1(4) . . ?
N5 C9 H91 108.5 . . ?
C6 C9 H91 108.5 . . ?
N5 C9 H92 108.5 . . ?
C6 C9 H92 108.5 . . ?
H91 C9 H92 107.5 . . ?
N5 C10 C11 121.1(2) . 3_567 ?
N5 C10 C11 121.1(2) . . ?
C11 C10 C11 117.8(4) 3_567 . ?
C12 C11 C10 121.6(3) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C1 C12 C11 119.3(3) . . ?
C1 C12 C13 120.2(3) . . ?
C11 C12 C13 120.4(3) . . ?
O3 C13 O4 123.9(4) . . ?
O3 C13 C12 121.4(3) . . ?
O4 C13 C12 114.8(3) . . ?
N1 C14 N1 111.7(5) . 11 ?
N1 C14 C15 124.0(3) . . ?
N1 C14 C15 124.0(3) 11 . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C15 H15A 109.5(13) . 11 ?
H15A C15 H15A 29.3 . 11 ?
H15B C15 H15A 82.6 . 11 ?
H15C C15 H15A 131.8 . 11 ?
C14 C15 H15B 109.5(12) . 11 ?
H15A C15 H15B 82.6 . 11 ?
H15B C15 H15B 131.8 . 11 ?
H15C C15 H15B 29.3 . 11 ?
H15A C15 H15B 109.5 11 11 ?
C14 C15 H15C 109(2) . 11 ?
H15A C15 H15C 131.8 . 11 ?
H15B C15 H15C 29.3 . 11 ?
H15C C15 H15C 82.6 . 11 ?
H15A C15 H15C 109.5 11 11 ?
H15B C15 H15C 109.5 11 11 ?
N4 C16 N4 114.4(6) 10_557 . ?
N4 C16 C17 122.3(3) 10_557 . ?
N4 C16 C17 122.3(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C17 H17A 109.5(8) . 10_557 ?
H17A C17 H17A 136.5 . 10_557 ?
H17B C17 H17A 37.9 . 10_557 ?
H17C C17 H17A 74.3 . 10_557 ?
C16 C17 H17B 109(2) . 10_557 ?
H17A C17 H17B 37.9 . 10_557 ?
H17B C17 H17B 74.3 . 10_557 ?
H17C C17 H17B 136.5 . 10_557 ?
H17A C17 H17B 109.5 10_557 10_557 ?
C16 C17 H17C 109.5(16) . 10_557 ?
H17A C17 H17C 74.3 . 10_557 ?
H17B C17 H17C 136.5 . 10_557 ?
H17C C17 H17C 37.9 . 10_557 ?
H17A C17 H17C 109.5 10_557 10_557 ?
H17B C17 H17C 109.5 10_557 10_557 ?

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
C14 N1 N2 N2 -2.1(5) . . . 11 ?
Zn1 N1 N2 N2 176.7(2) . . . 11 ?
N3 N3 N4 C16 -3.1(5) 10_557 . . . ?
N3 N3 N4 Zn1 -173.04(15) 10_557 . . . ?
Zn1 O2 C2 O1 -3.7(6) . . . . ?
Zn1 O2 C2 C3 172.8(3) . . . . ?
O2 C2 C3 C8 2.2(6) . . . . ?
O1 C2 C3 C8 178.9(4) . . . . ?
O2 C2 C3 C4 -177.7(4) . . . . ?
O1 C2 C3 C4 -1.0(6) . . . . ?
C8 C3 C4 C5 -1.2(7) . . . . ?
C2 C3 C4 C5 178.7(4) . . . . ?
C3 C4 C5 C6 1.2(8) . . . . ?
C4 C5 C6 C7 -0.3(7) . . . . ?
C4 C5 C6 C9 -179.6(4) . . . . ?
C5 C6 C7 C8 -0.6(7) . . . . ?
C9 C6 C7 C8 178.7(4) . . . . ?
C4 C3 C8 C7 0.3(7) . . . . ?
C2 C3 C8 C7 -179.5(4) . . . . ?
C6 C7 C8 C3 0.6(7) . . . . ?
C10 N5 C9 C6 75.2(5) . . . . ?
C9 N5 C9 C6 -104.8(5) 3_567 . . . ?
C7 C6 C9 N5 28.7(7) . . . . ?
C5 C6 C9 N5 -152.1(5) . . . . ?
C9 N5 C10 C11 -10.3(3) . . . 3_567 ?
C9 N5 C10 C11 169.7(3) 3_567 . . 3_567 ?
C9 N5 C10 C11 169.7(3) . . . . ?
C9 N5 C10 C11 -10.3(3) 3_567 . . . ?
N5 C10 C11 C12 179.9(3) . . . . ?
C11 C10 C11 C12 -0.1(3) 3_567 . . . ?
C12 C1 C12 C11 -0.1(2) 3_567 . . . ?
C12 C1 C12 C13 -177.4(4) 3_567 . . . ?
C10 C11 C12 C1 0.2(5) . . . . ?
C10 C11 C12 C13 177.5(3) . . . . ?
Zn1 O4 C13 O3 -1.0(6) 15_545 . . . ?
Zn1 O4 C13 C12 179.9(3) 15_545 . . . ?
C1 C12 C13 O3 -169.2(4) . . . . ?
C11 C12 C13 O3 13.5(6) . . . . ?
C1 C12 C13 O4 9.9(5) . . . . ?
C11 C12 C13 O4 -167.4(4) . . . . ?
N2 N1 C14 N1 3.5(8) . . . 11 ?
Zn1 N1 C14 N1 -175.2(2) . . . 11 ?
N2 N1 C14 C15 178.6(7) . . . . ?
Zn1 N1 C14 C15 0.0(10) . . . . ?
N3 N4 C16 N4 5.4(8) . . . 10_557 ?
Zn1 N4 C16 N4 172.44(18) . . . 10_557 ?
N3 N4 C16 C17 174.5(8) . . . . ?
Zn1 N4 C16 C17 -18.5(12) . . . . ?

_refine_diff_density_max         0.651
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.068




