# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_c_sq
_database_code_depnum_ccdc_archive 'CCDC 1890023'
loop_
_audit_author_name
_audit_author_address
'Zhichao Shao'
;Zhengzhou University
China
;
_audit_update_record             
;
2019-01-10 deposited with the CCDC.	2019-10-09 downloaded from the CCDC.
;
_audit_creation_date             2019-01-07
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.33(C36 H30 N12 O12 Zn3)'
_chemical_formula_sum            'C12 H10 N4 O4 Zn'
_chemical_formula_weight         339.61
_chemical_absolute_configuration ?
_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      hexagonal
_space_group_IT_number           171
_space_group_name_H-M_alt        'P 62'
_space_group_name_Hall           'P 62'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x-y, x, z+1/3'
'-y, x-y, z+2/3'
'-x, -y, z'
'-x+y, -x, z+1/3'
'y, -x+y, z+2/3'

_cell_length_a                   15.465(3)
_cell_length_b                   15.465(3)
_cell_length_c                   6.3597(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1317.2(6)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    4472
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.8884
_cell_measurement_theta_min      2.6340
_shelx_estimated_absorpt_T_max   0.883
_shelx_estimated_absorpt_T_min   0.849
_exptl_absorpt_coefficient_mu    1.415
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7004
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            13194
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.485
_diffrn_reflns_theta_min         3.042
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.822
_reflns_Friedel_fraction_full    0.967
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                1571
_reflns_number_total             1585
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.113
_refine_diff_density_min         -0.114
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.948(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.777
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1585
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0192
_refine_ls_R_factor_gt           0.0190
_refine_ls_restrained_S_all      0.777
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0328P)²+0.4301P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0459
_refine_ls_wR_factor_ref         0.0461
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.052(18)
 0.948(18)
2. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5)
3.b X=CH2 refined with riding coordinates:
 N2(H2B,H2A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Zn1 Zn 0.500000 0.500000 0.48064(9) 0.03543(13) Uani 1 2 d S T P . .
O1 O 0.29511(18) 0.4267(2) 0.5575(4) 0.0705(8) Uani 1 1 d . . . . .
O2 O 0.39501(13) 0.48155(15) 0.2829(3) 0.0453(5) Uani 1 1 d . . . . .
N1 N 0.09808(14) 0.48235(16) -0.0041(4) 0.0391(5) Uani 1 1 d . . . . .
N2 N 0.10019(19) 0.3736(2) 0.4964(5) 0.0628(7) Uani 1 1 d . . . . .
H2B H 0.038539 0.350180 0.529682 0.075 Uiso 1 1 calc R . . . .
H2A H 0.139387 0.365666 0.580030 0.075 Uiso 1 1 calc R . . . .
C1 C 0.07109(18) 0.4352(2) 0.1782(5) 0.0423(6) Uani 1 1 d . . . . .
H1 H 0.004940 0.408564 0.219855 0.076(12) Uiso 1 1 calc R . . . .
C2 C 0.13560(18) 0.4230(2) 0.3120(5) 0.0408(5) Uani 1 1 d . . . . .
C3 C 0.23483(19) 0.4629(2) 0.2467(4) 0.0355(6) Uani 1 1 d . . . . .
C4 C 0.26181(19) 0.5117(2) 0.0551(5) 0.0432(7) Uani 1 1 d . . . . .
H4 H 0.327177 0.538491 0.007921 0.060(9) Uiso 1 1 calc R . . . .
C5 C 0.19342(19) 0.5215(2) -0.0671(5) 0.0436(6) Uani 1 1 d . . . . .
H5 H 0.213471 0.555414 -0.194466 0.067(10) Uiso 1 1 calc R . . . .
C6 C 0.3118(2) 0.4541(2) 0.3747(5) 0.0419(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O2 1.9587(19) 4_665 ?
Zn1 O2 1.9587(19) . ?
Zn1 N1 2.032(2) 3_665 ?
Zn1 N1 2.032(2) 6 ?
O1 C6 1.220(3) . ?
O2 C6 1.278(3) . ?
N1 C1 1.321(4) . ?
N1 C5 1.345(3) . ?
N2 H2B 0.8600 . ?
N2 H2A 0.8600 . ?
N2 C2 1.357(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.394(4) . ?
C2 C3 1.401(3) . ?
C3 C4 1.383(4) . ?
C3 C6 1.503(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.380(4) . ?
C5 H5 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
O2 Zn1 O2 100.10(12) 4_665 . ?
O2 Zn1 N1 120.06(9) . 6 ?
O2 Zn1 N1 103.33(8) 4_665 6 ?
O2 Zn1 N1 103.33(8) . 3_665 ?
O2 Zn1 N1 120.06(9) 4_665 3_665 ?
N1 Zn1 N1 110.56(13) 3_665 6 ?
C6 O2 Zn1 112.28(19) . . ?
C1 N1 Zn1 121.52(16) . 2_554 ?
C1 N1 C5 118.9(2) . . ?
C5 N1 Zn1 119.6(2) . 2_554 ?
H2B N2 H2A 120.0 . . ?
C2 N2 H2B 120.0 . . ?
C2 N2 H2A 120.0 . . ?
N1 C1 H1 118.0 . . ?
N1 C1 C2 124.1(2) . . ?
C2 C1 H1 118.0 . . ?
N2 C2 C1 119.3(2) . . ?
N2 C2 C3 123.3(3) . . ?
C1 C2 C3 117.4(3) . . ?
C2 C3 C6 122.8(3) . . ?
C4 C3 C2 117.8(2) . . ?
C4 C3 C6 119.4(2) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.1(2) . . ?
C5 C4 H4 119.4 . . ?
N1 C5 C4 120.7(3) . . ?
N1 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
O1 C6 O2 123.6(3) . . ?
O1 C6 C3 120.6(3) . . ?
O2 C6 C3 115.7(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O2 C6 O1 -11.3(4) . . . . ?
Zn1 O2 C6 C3 165.27(18) . . . . ?
Zn1 N1 C1 C2 -178.3(2) 2_554 . . . ?
Zn1 N1 C5 C4 179.1(2) 2_554 . . . ?
N1 C1 C2 N2 179.8(3) . . . . ?
N1 C1 C2 C3 -0.5(4) . . . . ?
N2 C2 C3 C4 -180.0(3) . . . . ?
N2 C2 C3 C6 0.4(4) . . . . ?
C1 N1 C5 C4 0.7(4) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C1 C2 C3 C6 -179.4(2) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C2 C3 C6 O1 -12.7(4) . . . . ?
C2 C3 C6 O2 170.6(3) . . . . ?
C3 C4 C5 N1 -0.9(5) . . . . ?
C4 C3 C6 O1 167.7(3) . . . . ?
C4 C3 C6 O2 -9.0(4) . . . . ?
C5 N1 C1 C2 0.0(4) . . . . ?
C6 C3 C4 C5 -180.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.052(18)
2 0.948(18)

####################################################################### 
# 
# 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_mo_190107c_0ma_sq
_database_code_depnum_ccdc_archive 'CCDC 1890024'
loop_
_audit_author_name
_audit_author_address
'Zhichao Shao'
;Zhengzhou University
China
;
_audit_update_record             
;
2019-01-10 deposited with the CCDC.	2019-10-09 downloaded from the CCDC.
;
_audit_creation_date             2019-01-10
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10 N4 O4 Zn'
_chemical_formula_sum            'C12 H10 N4 O4 Zn'
_chemical_formula_weight         339.61
_chemical_absolute_configuration ?
_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      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   14.7391(5)
_cell_length_b                   14.7855(5)
_cell_length_c                   9.8812(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2153.36(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9650
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      2.48
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.154
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0554 before and 0.0487 after correction.
The Ratio of minimum to maximum transmission is 0.9504.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.048
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0116
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            68415
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.484
_diffrn_reflns_theta_min         2.764
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3729
_reflns_number_total             3986
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.26(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3986
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0273
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0543P)²+1.0213P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0867
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.74(2)
 0.26(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
3. Rigid bond restraints
 C9, C10
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.01
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C7(H7), C10(H10), C11(H11)
4.b X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N4(H4A,H4B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.72071(2) 0.75207(2) 0.74515(3) 0.02026(13) Uani 1 1 d . . . . .
O1 O 0.52564(16) 0.7455(3) 0.7042(2) 0.0425(6) Uani 1 1 d . . . . .
O2 O 0.62103(13) 0.7555(2) 0.8762(2) 0.0305(5) Uani 1 1 d . . . . .
O3 O 0.7760(2) 1.13763(17) 0.3524(3) 0.0372(6) Uani 1 1 d . . . . .
O4 O 0.6523(2) 1.18481(18) 0.4617(3) 0.0441(7) Uani 1 1 d . . . . .
N1 N 0.32659(17) 0.7453(2) 1.1184(2) 0.0268(6) Uani 1 1 d . . . . .
N2 N 0.3509(2) 0.6960(3) 0.7598(3) 0.0443(8) Uani 1 1 d . . . . .
H2A H 0.2960 0.6796 0.7433 0.053 Uiso 1 1 calc R . . . .
H2B H 0.3906 0.6956 0.6961 0.053 Uiso 1 1 calc R . . . .
N3 N 0.7210(2) 0.87202(18) 0.6445(3) 0.0262(6) Uani 1 1 d . . . . .
N4 N 0.5927(3) 1.0792(2) 0.6661(5) 0.0607(12) Uani 1 1 d . . . . .
H4A H 0.5584 1.0655 0.7335 0.073 Uiso 1 1 calc R . . . .
H4B H 0.5879 1.1313 0.6281 0.073 Uiso 1 1 calc R . . . .
C1 C 0.4113(2) 0.7669(3) 1.1539(4) 0.0343(9) Uani 1 1 d . . . . .
H1 H 0.4237 0.7832 1.2429 0.041 Uiso 1 1 calc R . . . .
C2 C 0.4800(2) 0.7654(3) 1.0611(4) 0.0345(8) Uani 1 1 d . . . . .
H2 H 0.5388 0.7787 1.0891 0.041 Uiso 1 1 calc R . . . .
C3 C 0.4648(2) 0.7451(2) 0.9285(3) 0.0251(6) Uani 1 1 d . . . . .
C4 C 0.3750(2) 0.7229(2) 0.8880(3) 0.0291(8) Uani 1 1 d . . . . .
C5 C 0.3102(2) 0.7236(3) 0.9921(3) 0.0300(8) Uani 1 1 d . . . . .
H5 H 0.2511 0.7074 0.9697 0.036 Uiso 1 1 calc R . . . .
C6 C 0.5408(2) 0.7491(3) 0.8266(3) 0.0263(6) Uani 1 1 d . . . . .
C7 C 0.6604(3) 0.9340(2) 0.6836(4) 0.0313(8) Uani 1 1 d . . . . .
H7 H 0.6217 0.9201 0.7549 0.038 Uiso 1 1 calc R . . . .
C8 C 0.6523(3) 1.0204(2) 0.6210(4) 0.0334(8) Uani 1 1 d . . . . .
C9 C 0.7132(2) 1.0379(2) 0.5110(3) 0.0246(7) Uani 1 1 d . U . . .
C10 C 0.7717(3) 0.9714(2) 0.4725(4) 0.0349(8) Uani 1 1 d . U . . .
H10 H 0.8099 0.9811 0.3990 0.042 Uiso 1 1 calc R . . . .
C11 C 0.7755(3) 0.8887(2) 0.5410(4) 0.0333(8) Uani 1 1 d . . . . .
H11 H 0.8169 0.8450 0.5135 0.040 Uiso 1 1 calc R . . . .
C12 C 0.7122(3) 1.1267(2) 0.4390(4) 0.0295(8) 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 O2 1.959(2) . ?
Zn1 O3 1.948(2) 3_646 ?
Zn1 N1 2.063(2) 4_567 ?
Zn1 N3 2.033(3) . ?
O1 C6 1.231(4) . ?
O2 C6 1.284(4) . ?
O3 Zn1 1.948(2) 3_656 ?
O3 C12 1.281(5) . ?
O4 C12 1.252(5) . ?
N1 Zn1 2.063(2) 4_467 ?
N1 C1 1.336(4) . ?
N1 C5 1.312(4) . ?
N2 C4 1.374(4) . ?
N3 C7 1.336(4) . ?
N3 C11 1.325(5) . ?
N4 C8 1.314(5) . ?
C1 C2 1.366(5) . ?
C2 C3 1.363(5) . ?
C3 C4 1.421(5) . ?
C3 C6 1.507(4) . ?
C4 C5 1.403(5) . ?
C7 C8 1.424(5) . ?
C8 C9 1.434(5) . ?
C9 C10 1.362(5) . ?
C9 C12 1.494(5) . ?
C10 C11 1.398(5) . ?

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
O2 Zn1 N1 97.75(10) . 4_567 ?
O2 Zn1 N3 107.60(12) . . ?
O3 Zn1 O2 111.60(13) 3_646 . ?
O3 Zn1 N1 108.74(13) 3_646 4_567 ?
O3 Zn1 N3 121.02(11) 3_646 . ?
N3 Zn1 N1 107.56(13) . 4_567 ?
C6 O2 Zn1 115.9(2) . . ?
C12 O3 Zn1 117.3(2) . 3_656 ?
C1 N1 Zn1 122.1(2) . 4_467 ?
C5 N1 Zn1 119.2(2) . 4_467 ?
C5 N1 C1 118.7(3) . . ?
C7 N3 Zn1 117.1(2) . . ?
C11 N3 Zn1 122.8(2) . . ?
C11 N3 C7 120.1(3) . . ?
N1 C1 C2 120.8(3) . . ?
C3 C2 C1 121.8(3) . . ?
C2 C3 C4 118.4(3) . . ?
C2 C3 C6 120.7(3) . . ?
C4 C3 C6 120.9(3) . . ?
N2 C4 C3 124.6(3) . . ?
N2 C4 C5 120.1(3) . . ?
C5 C4 C3 115.2(3) . . ?
N1 C5 C4 125.1(3) . . ?
O1 C6 O2 123.1(3) . . ?
O1 C6 C3 121.3(3) . . ?
O2 C6 C3 115.6(3) . . ?
N3 C7 C8 123.1(3) . . ?
N4 C8 C7 120.2(3) . . ?
N4 C8 C9 123.8(3) . . ?
C7 C8 C9 116.0(3) . . ?
C8 C9 C12 120.9(3) . . ?
C10 C9 C8 118.5(3) . . ?
C10 C9 C12 120.6(3) . . ?
C9 C10 C11 121.4(3) . . ?
N3 C11 C10 120.8(3) . . ?
O3 C12 C9 114.9(3) . . ?
O4 C12 O3 123.4(3) . . ?
O4 C12 C9 121.7(3) . . ?

_platon_squeeze_details          ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.006 0.000 0.022 1063 561 ' '

_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.74(2)
2 0.26(2)

