# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_1cp
_database_code_depnum_ccdc_archive 'CCDC 1944820'
loop_
_audit_author_name
_audit_author_address
'Arpan Hazra'
;Stellenbosch University
South Africa
;
_audit_update_record             
;
2019-08-01 deposited with the CCDC.	2019-09-06 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            'C18 H10 N O4 Zn'
_chemical_formula_weight         369.64

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      orthorhombic
_space_group_IT_number           69
_space_group_name_H-M_alt        'F m m m'
_space_group_name_Hall           '-F 2 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'
'x, -y, -z'
'-x, y, -z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x, -y+1/2, -z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+1/2, -y, -z+1/2'
'-x+1/2, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, y, -z'
'-x, y, z'
'x, -y, z'
'-x, -y+1/2, -z+1/2'
'x, y+1/2, -z+1/2'
'-x, y+1/2, z+1/2'
'x, -y+1/2, z+1/2'
'-x+1/2, -y, -z+1/2'
'x+1/2, y, -z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z+1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, -z'
'-x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z'

_cell_length_a                   10.7494(11)
_cell_length_b                   16.2516(15)
_cell_length_c                   18.7137(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3269.2(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6042
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      25.37

_exptl_crystal_description       block
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_F_000             1496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.012
_exptl_crystal_size_mid          0.007
_exptl_crystal_size_min          0.005
_exptl_absorpt_coefficient_mu    1.523
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   EMPIRICAL
_exptl_absorpt_correction_T_min  0.9142
_exptl_absorpt_correction_T_max  0.9876
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11630
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_av_R_equivalents  0.0750
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.519
_diffrn_reflns_theta_max         25.370
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             852
_reflns_number_gt                712
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT  A'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0900P)²+79.5747P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   NOREF
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         852
_refine_ls_number_parameters     73
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0719
_refine_ls_wR_factor_ref         0.1945
_refine_ls_wR_factor_gt          0.1782
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.094
_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 0.500000 0.40863(8) 0.500000 0.0350(5) Uani 1 4 d S T P B .
O1 O 0.6285(6) 0.4325(3) 0.5774(3) 0.0609(14) Uani 1 1 d . . . . .
N1 N 0.500000 0.2834(6) 0.500000 0.044(3) Uani 1 4 d S T P . .
C1 C 0.6510(10) 0.500000 0.6056(4) 0.047(2) Uani 1 2 d S T P A .
C2 C 0.7044(13) 0.500000 0.6800(5) 0.066(3) Uani 1 2 d S TU P . .
C3 C 0.6752(15) 0.5703(7) 0.7254(5) 0.069(4) Uani 0.5 1 d G U P A -1
C4 C 0.600(2) 0.6345(10) 0.7023(8) 0.095(7) Uani 0.25 1 d G . P A -1
H4 H 0.570258 0.635087 0.655594 0.114 Uiso 0.25 1 calc R U P A -1
C5 C 0.569(2) 0.6977(10) 0.7490(11) 0.095(7) Uani 0.25 1 d G . P A -1
H5 H 0.518158 0.740662 0.733488 0.114 Uiso 0.25 1 calc R U P A -1
C6 C 0.613(2) 0.6968(11) 0.8188(10) 0.095(7) Uani 0.25 1 d G . P A -1
H6 H 0.591900 0.739121 0.849993 0.114 Uiso 0.25 1 calc R U P A -1
C7 C 0.688(2) 0.6326(11) 0.8419(6) 0.095(7) Uani 0.25 1 d G . P A -1
H7 H 0.717740 0.632004 0.888604 0.114 Uiso 0.25 1 calc R U P A -1
C8 C 0.7194(13) 0.5694(7) 0.7952(6) 0.083(7) Uani 0.5 1 d G . P A -1
C9 C 0.4115(18) 0.2426(13) 0.4656(9) 0.091(3) Uani 0.5 1 d . U P B -1
H9 H 0.349604 0.272031 0.442128 0.110 Uiso 0.5 1 calc R U P B -1
C10 C 0.408(2) 0.1574(12) 0.4637(10) 0.091(3) Uani 0.5 1 d . U P B -1
H10 H 0.346632 0.129572 0.438704 0.110 Uiso 0.5 1 calc R U P B -1
C11 C 0.500000 0.1151(14) 0.500000 0.091(3) Uani 1 4 d S TU P . .
C12 C 0.500690 0.027230 0.469200 0.131(15) Uani 0.25 1 d S U P B -1
H12A H 0.545750 0.022160 0.442780 0.196 Uiso 0.25 1 d R U P B -1
H12B H 0.454250 0.022160 0.442780 0.196 Uiso 0.25 1 d R U P B -1


_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 N1 2.036(10) . ?
Zn1 O1 2.039(5) 4_656 ?
Zn1 O1 2.039(5) 18_556 ?
Zn1 O1 2.039(5) 19_655 ?
Zn1 O1 2.039(5) . ?
Zn1 Zn1 2.970(3) 17_666 ?
O1 C1 1.241(6) . ?
N1 C9 1.326(19) . ?
C1 C2 1.505(12) . ?
C2 C3 1.458(12) . ?
C3 C4 1.3900 . ?
C3 C8 1.3900 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C6 C7 1.3900 . ?
C7 C8 1.3900 . ?
C9 C10 1.39(3) . ?
C10 C11 1.38(2) . ?
C11 C12 1.54(2) . ?

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
N1 Zn1 O1 100.97(14) . 4_656 ?
N1 Zn1 O1 100.97(14) . 18_556 ?
O1 Zn1 O1 85.3(3) 4_656 18_556 ?
N1 Zn1 O1 100.97(14) . 19_655 ?
O1 Zn1 O1 90.5(3) 4_656 19_655 ?
O1 Zn1 O1 158.1(3) 18_556 19_655 ?
N1 Zn1 O1 100.97(14) . . ?
O1 Zn1 O1 158.1(3) 4_656 . ?
O1 Zn1 O1 90.5(3) 18_556 . ?
O1 Zn1 O1 85.3(3) 19_655 . ?
N1 Zn1 Zn1 180.0 . 17_666 ?
O1 Zn1 Zn1 79.03(14) 4_656 17_666 ?
O1 Zn1 Zn1 79.03(14) 18_556 17_666 ?
O1 Zn1 Zn1 79.03(14) 19_655 17_666 ?
O1 Zn1 Zn1 79.03(14) . 17_666 ?
C1 O1 Zn1 127.1(5) . . ?
C9 N1 Zn1 120.0(10) . . ?
O1 C1 O1 124.2(8) . 20_565 ?
O1 C1 C2 117.9(4) . . ?
O1 C1 C2 117.9(4) 20_565 . ?
C3 C2 C1 117.2(7) . . ?
C4 C3 C8 120.0 . . ?
C4 C3 C2 122.1(9) . . ?
C8 C3 C2 117.8(9) . . ?
C3 C4 C5 120.0 . . ?
C6 C5 C4 120.0 . . ?
C5 C6 C7 120.0 . . ?
C6 C7 C8 120.0 . . ?
C7 C8 C3 120.0 . . ?
N1 C9 C10 121.9(19) . . ?
C11 C10 C9 118(2) . . ?
C10 C11 C12 106.3(10) . . ?

_refine_diff_density_max         0.871
_refine_diff_density_min         -1.696
_refine_diff_density_rms         0.131


_exptl_crystal_recrystallization_method Hydrothermal
_chemical_properties_physical    Heat-sensitive
####################################################################### 
# 
# 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_1cp(des)
_database_code_depnum_ccdc_archive 'CCDC 1944823'
loop_
_audit_author_name
_audit_author_address
'Arpan Hazra'
;Stellenbosch University
South Africa
;
_audit_update_record             
;
2019-08-07 deposited with the CCDC.	2019-09-06 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            'C18 H10 N O4 Zn'
_chemical_formula_weight         369.64

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      orthorhombic
_space_group_IT_number           69
_space_group_name_H-M_alt        'F m m m'
_space_group_name_Hall           '-F 2 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'
'x, -y, -z'
'-x, y, -z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x, -y+1/2, -z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+1/2, -y, -z+1/2'
'-x+1/2, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, y, -z'
'-x, y, z'
'x, -y, z'
'-x, -y+1/2, -z+1/2'
'x, y+1/2, -z+1/2'
'-x, y+1/2, z+1/2'
'x, -y+1/2, z+1/2'
'-x+1/2, -y, -z+1/2'
'x+1/2, y, -z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z+1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, -z'
'-x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z'

_cell_length_a                   10.7054(7)
_cell_length_b                   16.2225(11)
_cell_length_c                   18.7784(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3261.2(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    8637
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      26.25

_exptl_crystal_description       block
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_F_000             1496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.012
_exptl_crystal_size_mid          0.007
_exptl_crystal_size_min          0.005
_exptl_absorpt_coefficient_mu    1.527
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   EMPIRICAL
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19461
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.0737
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.169
_diffrn_reflns_theta_max         26.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             956
_reflns_number_gt                731
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT  A'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1097P)²+43.3569P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   NOREF
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         956
_refine_ls_number_parameters     82
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0713
_refine_ls_wR_factor_ref         0.2070
_refine_ls_wR_factor_gt          0.1882
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.085
_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 0.500000 0.40935(6) 0.500000 0.0520(6) Uani 1 4 d S T P B .
O1 O 0.6287(5) 0.4331(3) 0.5774(2) 0.0718(13) Uani 1 1 d . . . . .
N1 N 0.500000 0.2838(6) 0.500000 0.059(3) Uani 1 4 d S T P . .
C1 C 0.6520(8) 0.500000 0.6056(4) 0.054(2) Uani 1 2 d S T P A .
C2 C 0.7062(10) 0.500000 0.6794(5) 0.071(2) Uani 1 2 d S TU P . .
C3 C 0.6839(13) 0.4251(7) 0.7247(5) 0.079(3) Uani 0.5 1 d G U P A -1
C4 C 0.7252(11) 0.4281(7) 0.7948(6) 0.094(6) Uani 0.5 1 d G . P A -1
C5 C 0.702(2) 0.3625(10) 0.8405(5) 0.108(6) Uani 0.25 1 d G . P A -1
H5 H 0.729178 0.364451 0.887419 0.130 Uiso 0.25 1 calc R U P A -1
C6 C 0.637(2) 0.2939(10) 0.8160(9) 0.108(6) Uani 0.25 1 d G . P A -1
H6 H 0.620826 0.249989 0.846551 0.130 Uiso 0.25 1 calc R U P A -1
C7 C 0.595(2) 0.2909(9) 0.7459(10) 0.108(6) Uani 0.25 1 d G . P A -1
H7 H 0.551944 0.245047 0.729490 0.130 Uiso 0.25 1 calc R U P A -1
C8 C 0.619(2) 0.3565(9) 0.7002(7) 0.108(6) Uani 0.25 1 d G . P A -1
H8 H 0.591414 0.354567 0.653296 0.130 Uiso 0.25 1 calc R U P A -1
C9 C 0.5862(14) 0.2427(8) 0.4643(7) 0.079(4) Uani 0.5 1 d . U P B -1
H9 H 0.646474 0.272043 0.439253 0.095 Uiso 0.5 1 calc R U P B -1
C10 C 0.590(2) 0.1576(11) 0.4629(11) 0.120(7) Uani 0.5 1 d . U P B -1
H10 H 0.651254 0.129661 0.437561 0.144 Uiso 0.5 1 calc R U P B -1
C11 C 0.500000 0.1158(16) 0.500000 0.128(7) Uani 1 4 d S TU P . .
C12 C 0.500000 0.027640 0.467950 0.116(8) Uani 0.25 1 d S U P B -1
H12A H 0.442150 0.017600 0.436540 0.140 Uiso 0.25 1 d R U P B -1
H12B H 0.557850 0.017600 0.436540 0.140 Uiso 0.25 1 d R U P B -1


_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 N1 2.037(9) . ?
Zn1 O1 2.039(5) 4_656 ?
Zn1 O1 2.039(5) 19_655 ?
Zn1 O1 2.039(5) 18_556 ?
Zn1 O1 2.039(5) . ?
Zn1 Zn1 2.941(2) 17_666 ?
O1 C1 1.234(5) . ?
N1 C9 1.321(14) . ?
C1 C2 1.502(10) . ?
C2 C3 1.502(11) . ?
C3 C4 1.3900 . ?
C3 C8 1.3900 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C6 C7 1.3900 . ?
C7 C8 1.3900 . ?
C9 C10 1.38(2) . ?
C10 C11 1.37(2) . ?
C11 C12 1.55(2) . ?

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
N1 Zn1 O1 100.87(13) . 4_656 ?
N1 Zn1 O1 100.87(13) . 19_655 ?
O1 Zn1 O1 90.9(3) 4_656 19_655 ?
N1 Zn1 O1 100.87(13) . 18_556 ?
O1 Zn1 O1 85.0(3) 4_656 18_556 ?
O1 Zn1 O1 158.3(3) 19_655 18_556 ?
N1 Zn1 O1 100.87(13) . . ?
O1 Zn1 O1 158.3(3) 4_656 . ?
O1 Zn1 O1 85.0(3) 19_655 . ?
O1 Zn1 O1 90.9(3) 18_556 . ?
N1 Zn1 Zn1 180.0 . 17_666 ?
O1 Zn1 Zn1 79.13(13) 4_656 17_666 ?
O1 Zn1 Zn1 79.13(13) 19_655 17_666 ?
O1 Zn1 Zn1 79.13(13) 18_556 17_666 ?
O1 Zn1 Zn1 79.13(13) . 17_666 ?
C1 O1 Zn1 127.5(5) . . ?
C9 N1 Zn1 120.3(7) . . ?
O1 C1 O1 123.3(7) 20_565 . ?
O1 C1 C2 118.3(4) 20_565 . ?
O1 C1 C2 118.3(4) . . ?
C1 C2 C3 117.5(6) . . ?
C4 C3 C8 120.0 . . ?
C4 C3 C2 117.3(8) . . ?
C8 C3 C2 122.6(8) . . ?
C5 C4 C3 120.0 . . ?
C4 C5 C6 120.0 . . ?
C7 C6 C5 120.0 . . ?
C6 C7 C8 120.0 . . ?
C7 C8 C3 120.0 . . ?
N1 C9 C10 122.2(15) . . ?
C11 C10 C9 118(2) . . ?
C10 C11 C12 105.0(10) . . ?

_refine_diff_density_max         0.984
_refine_diff_density_min         -1.022
_refine_diff_density_rms         0.111


_chemical_properties_physical    Heat-sensitive
####################################################################### 
# 
# 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_1lp
_database_code_depnum_ccdc_archive 'CCDC 1944821'
loop_
_audit_author_name
_audit_author_address
'Arpan Hazra'
;Stellenbosch University
South Africa
;
_audit_update_record             
;
2019-08-07 deposited with the CCDC.	2019-09-06 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            'C19 H12 N O6 Zn'
_chemical_formula_weight         415.67

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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2, y+1/2, z'
'-x+1/2, y+1/2, -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'

_cell_length_a                   16.556(8)
_cell_length_b                   14.296(7)
_cell_length_c                   16.325(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.679(12)
_cell_angle_gamma                90
_cell_volume                     3829(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    4785
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      25.35

_exptl_crystal_description       block
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_F_000             1688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.012
_exptl_crystal_size_mid          0.007
_exptl_crystal_size_min          0.005
_exptl_absorpt_coefficient_mu    1.316
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   EMPIRICAL
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14165
_diffrn_reflns_av_unetI/netI     0.1512
_diffrn_reflns_av_R_equivalents  0.1154
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.176
_diffrn_reflns_theta_max         25.003
_diffrn_reflns_theta_full        25.003
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             3329
_reflns_number_gt                1795
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT  A'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1948P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   NOREF
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3329
_refine_ls_number_parameters     205
_refine_ls_number_restraints     55
_refine_ls_R_factor_all          0.1820
_refine_ls_R_factor_gt           0.1048
_refine_ls_wR_factor_ref         0.3259
_refine_ls_wR_factor_gt          0.2707
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.048
_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 0.48788(10) -0.19960(9) 0.65767(8) 0.0338(5) Uani 1 1 d . . . . .
O1 O 0.6022(6) -0.1053(6) 0.8329(5) 0.048(2) Uani 1 1 d . . . . .
O2 O 0.5724(6) -0.1003(7) 0.6961(5) 0.048(2) Uani 1 1 d . . . . .
O3 O 0.9208(6) 0.2036(6) 0.8161(6) 0.056(3) Uani 1 1 d . . . . .
O4 O 0.9096(7) 0.2006(7) 0.6792(6) 0.058(3) Uani 1 1 d . . . . .
O5 O 0.972799 -0.001300 0.915600 0.23(2) Uiso 0.5 1 d . . P A -1
O6 O 0.997300 -0.032500 0.779300 0.44(5) Uiso 0.5 1 d . . P A -1
O7 O 0.808970 -0.201290 0.823991 0.29(3) Uiso 0.5 1 d . . P . .
O8 O 0.752890 -0.169580 0.941730 0.41(4) Uiso 0.5 1 d . . P . .
N1 N 0.4908(8) -0.1934(8) 0.5364(6) 0.048(2) Uani 1 1 d . U . . .
C1 C 0.6187(8) -0.0809(8) 0.7605(8) 0.036(3) Uani 1 1 d . . . . .
C2 C 0.6924(9) -0.0239(9) 0.7554(7) 0.042(3) Uani 1 1 d . . . . .
C3 C 0.7146(9) 0.0380(11) 0.8181(8) 0.055(4) Uani 1 1 d . . . . .
H3 H 0.686153 0.039397 0.863565 0.066 Uiso 1 1 calc R U . . .
C4 C 0.7806(10) 0.0999(10) 0.8144(9) 0.055(4) Uani 1 1 d . . . . .
H4 H 0.796567 0.139886 0.858500 0.066 Uiso 1 1 calc R U . . .
C5 C 0.8224(8) 0.1019(10) 0.7449(7) 0.041(3) Uani 1 1 d . . . . .
C6 C 0.8004(11) 0.0363(11) 0.6812(10) 0.061(5) Uani 1 1 d . . . . .
C7 C 0.7343(8) -0.0281(10) 0.6858(8) 0.047(3) Uani 1 1 d . . . . .
C8 C 0.7196(9) -0.0965(11) 0.6237(9) 0.056(4) Uani 1 1 d . . . . .
H8 H 0.681212 -0.142551 0.630169 0.067 Uiso 1 1 calc R U . . .
C9 C 0.7573(13) -0.1001(13) 0.5550(12) 0.090(6) Uani 1 1 d . . . . .
H9 H 0.740864 -0.141638 0.512159 0.108 Uiso 1 1 calc R U . . .
C10 C 0.8276(15) -0.0332(15) 0.5515(13) 0.117(9) Uani 1 1 d . . . . .
H10 H 0.859002 -0.036833 0.508464 0.141 Uiso 1 1 calc R U . . .
C11 C 0.8442(13) 0.0308(11) 0.6104(9) 0.075(6) Uani 1 1 d . . . . .
H11 H 0.885590 0.073779 0.605865 0.090 Uiso 1 1 calc R U . . .
C12 C 0.8888(8) 0.1720(9) 0.7431(9) 0.043(3) Uani 1 1 d . . . . .
C13 C 0.5407(12) -0.2530(14) 0.4976(10) 0.077(2) Uani 1 1 d . U . . .
H13 H 0.569693 -0.298359 0.530126 0.093 Uiso 1 1 calc R U . . .
C14 C 0.5506(12) -0.2501(14) 0.4146(10) 0.077(2) Uani 1 1 d . U . . .
H14 H 0.580368 -0.295437 0.390907 0.093 Uiso 1 1 calc R U . . .
C15 C 0.5128(16) -0.1742(18) 0.3672(7) 0.112(6) Uani 1 1 d D U . . .
C16 C 0.4686(11) -0.1151(13) 0.4039(10) 0.077(2) Uani 1 1 d . U . . .
H16 H 0.441791 -0.066636 0.373462 0.093 Uiso 1 1 calc R U . . .
C17 C 0.4607(11) -0.1240(12) 0.4911(10) 0.077(2) Uani 1 1 d . U . . .
H17 H 0.432733 -0.077581 0.515599 0.093 Uiso 1 1 calc R U . . .
C18 C 0.534160 -0.162340 0.283529 0.128(6) Uani 1 1 d D U . . .
H18A H 0.571251 -0.212189 0.273220 0.153 Uiso 1 1 calc R U . . .
H18B H 0.563365 -0.103735 0.281568 0.153 Uiso 1 1 calc R U . . .
C19 C 0.973049 -0.029191 0.850101 0.17(3) Uiso 0.5 1 d . . P A -1
C20 C 0.783360 -0.182500 0.883770 0.20(3) Uiso 0.5 1 d . . 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 N1 1.988(10) . ?
Zn1 O4 1.991(9) 3_445 ?
Zn1 O1 2.031(9) 2_656 ?
Zn1 O2 2.032(9) . ?
Zn1 O3 2.052(9) 4_646 ?
Zn1 Zn1 2.988(3) 2_656 ?
O1 C1 1.296(15) . ?
O2 C1 1.247(15) . ?
O3 C12 1.317(16) . ?
O4 C12 1.211(16) . ?
O5 C19 1.1418(5) . ?
O6 C19 1.2741(5) . ?
O7 C20 1.1467(4) . ?
O8 C20 1.1452(5) . ?
N1 C17 1.298(19) . ?
N1 C13 1.40(2) . ?
C1 C2 1.479(17) . ?
C2 C3 1.366(17) . ?
C2 C7 1.409(18) . ?
C3 C4 1.414(19) . ?
C3 H3 0.9300 . ?
C4 C5 1.406(18) . ?
C4 H4 0.9300 . ?
C5 C6 1.412(19) . ?
C5 C12 1.490(17) . ?
C6 C7 1.44(2) . ?
C6 C11 1.447(19) . ?
C7 C8 1.407(19) . ?
C8 C9 1.36(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.51(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.33(2) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C13 C14 1.39(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.43(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.31(3) . ?
C15 C18 1.466(5) . ?
C16 C17 1.45(2) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C18 1.4652(5) 2_655 ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?

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
N1 Zn1 O4 108.1(5) . 3_445 ?
N1 Zn1 O1 99.3(4) . 2_656 ?
O4 Zn1 O1 87.7(4) 3_445 2_656 ?
N1 Zn1 O2 99.7(4) . . ?
O4 Zn1 O2 152.1(4) 3_445 . ?
O1 Zn1 O2 89.7(4) 2_656 . ?
N1 Zn1 O3 97.0(4) . 4_646 ?
O4 Zn1 O3 87.6(4) 3_445 4_646 ?
O1 Zn1 O3 163.6(4) 2_656 4_646 ?
O2 Zn1 O3 87.1(4) . 4_646 ?
N1 Zn1 Zn1 170.6(4) . 2_656 ?
O4 Zn1 Zn1 79.9(3) 3_445 2_656 ?
O1 Zn1 Zn1 85.7(3) 2_656 2_656 ?
O2 Zn1 Zn1 72.2(3) . 2_656 ?
O3 Zn1 Zn1 78.1(3) 4_646 2_656 ?
C1 O1 Zn1 119.6(8) . 2_656 ?
C1 O2 Zn1 137.4(9) . . ?
C12 O3 Zn1 128.1(9) . 4_656 ?
C12 O4 Zn1 131.3(10) . 3 ?
C17 N1 C13 114.4(13) . . ?
C17 N1 Zn1 122.9(10) . . ?
C13 N1 Zn1 121.3(10) . . ?
O2 C1 O1 121.9(12) . . ?
O2 C1 C2 119.6(11) . . ?
O1 C1 C2 118.4(11) . . ?
C3 C2 C7 121.3(12) . . ?
C3 C2 C1 117.1(11) . . ?
C7 C2 C1 121.4(12) . . ?
C2 C3 C4 120.3(13) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 121.0(13) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 118.3(13) . . ?
C4 C5 C12 118.3(12) . . ?
C6 C5 C12 123.4(12) . . ?
C5 C6 C7 120.7(13) . . ?
C5 C6 C11 121.1(14) . . ?
C7 C6 C11 118.2(14) . . ?
C8 C7 C2 123.7(12) . . ?
C8 C7 C6 117.8(13) . . ?
C2 C7 C6 118.3(13) . . ?
C9 C8 C7 124.6(15) . . ?
C9 C8 H8 117.7 . . ?
C7 C8 H8 117.7 . . ?
C8 C9 C10 116.7(16) . . ?
C8 C9 H9 121.7 . . ?
C10 C9 H9 121.7 . . ?
C11 C10 C9 119.6(17) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C6 122.5(16) . . ?
C10 C11 H11 118.7 . . ?
C6 C11 H11 118.7 . . ?
O4 C12 O3 122.4(12) . . ?
O4 C12 C5 122.6(13) . . ?
O3 C12 C5 114.9(12) . . ?
C14 C13 N1 125.4(17) . . ?
C14 C13 H13 117.3 . . ?
N1 C13 H13 117.3 . . ?
C13 C14 C15 116.9(16) . . ?
C13 C14 H14 121.6 . . ?
C15 C14 H14 121.6 . . ?
C16 C15 C14 118.2(12) . . ?
C16 C15 C18 124.7(19) . . ?
C14 C15 C18 116.8(17) . . ?
C15 C16 C17 121.3(16) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
N1 C17 C16 123.3(16) . . ?
N1 C17 H17 118.4 . . ?
C16 C17 H17 118.4 . . ?
C15 C18 C18 116.0(11) . 2_655 ?
C15 C18 H18A 108.3 . . ?
C18 C18 H18A 108.3 2_655 . ?
C15 C18 H18B 108.3 . . ?
C18 C18 H18B 108.3 2_655 . ?
H18A C18 H18B 107.4 . . ?
O5 C19 O6 154.632(12) . . ?
O8 C20 O7 174.132(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 C1 O1 -26(2) . . . . ?
Zn1 O2 C1 C2 157.3(10) . . . . ?
Zn1 O1 C1 O2 12.8(17) 2_656 . . . ?
Zn1 O1 C1 C2 -170.6(8) 2_656 . . . ?
O2 C1 C2 C3 143.9(14) . . . . ?
O1 C1 C2 C3 -32.8(19) . . . . ?
O2 C1 C2 C7 -31.5(19) . . . . ?
O1 C1 C2 C7 151.9(13) . . . . ?
C7 C2 C3 C4 0(2) . . . . ?
C1 C2 C3 C4 -175.1(13) . . . . ?
C2 C3 C4 C5 3(2) . . . . ?
C3 C4 C5 C6 -4(2) . . . . ?
C3 C4 C5 C12 177.1(13) . . . . ?
C4 C5 C6 C7 3(2) . . . . ?
C12 C5 C6 C7 -178.5(14) . . . . ?
C4 C5 C6 C11 -176.3(17) . . . . ?
C12 C5 C6 C11 2(2) . . . . ?
C3 C2 C7 C8 173.2(15) . . . . ?
C1 C2 C7 C8 -12(2) . . . . ?
C3 C2 C7 C6 -2(2) . . . . ?
C1 C2 C7 C6 173.6(13) . . . . ?
C5 C6 C7 C8 -175.1(14) . . . . ?
C11 C6 C7 C8 4(2) . . . . ?
C5 C6 C7 C2 0(2) . . . . ?
C11 C6 C7 C2 179.0(16) . . . . ?
C2 C7 C8 C9 177.8(18) . . . . ?
C6 C7 C8 C9 -7(3) . . . . ?
C7 C8 C9 C10 8(3) . . . . ?
C8 C9 C10 C11 -6(3) . . . . ?
C9 C10 C11 C6 4(3) . . . . ?
C5 C6 C11 C10 177(2) . . . . ?
C7 C6 C11 C10 -2(3) . . . . ?
Zn1 O4 C12 O3 -3(2) 3 . . . ?
Zn1 O4 C12 C5 173.9(9) 3 . . . ?
Zn1 O3 C12 O4 -2(2) 4_656 . . . ?
Zn1 O3 C12 C5 -179.5(8) 4_656 . . . ?
C4 C5 C12 O4 -155.1(15) . . . . ?
C6 C5 C12 O4 26(2) . . . . ?
C4 C5 C12 O3 22.1(19) . . . . ?
C6 C5 C12 O3 -156.6(14) . . . . ?
C17 N1 C13 C14 -9(3) . . . . ?
Zn1 N1 C13 C14 -175.8(15) . . . . ?
N1 C13 C14 C15 7(3) . . . . ?
C13 C14 C15 C16 -3(3) . . . . ?
C13 C14 C15 C18 170.3(17) . . . . ?
C14 C15 C16 C17 3(3) . . . . ?
C18 C15 C16 C17 -170.2(18) . . . . ?
C13 N1 C17 C16 8(3) . . . . ?
Zn1 N1 C17 C16 174.7(13) . . . . ?
C15 C16 C17 N1 -5(3) . . . . ?
C16 C15 C18 C18 -63(3) . . . 2_655 ?
C14 C15 C18 C18 123.7(18) . . . 2_655 ?

_refine_diff_density_max         1.677
_refine_diff_density_min         -1.044
_refine_diff_density_rms         0.178


_chemical_properties_physical    Heat-sensitive
####################################################################### 
# 
# 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_1np
_database_code_depnum_ccdc_archive 'CCDC 1944822'
loop_
_audit_author_name
_audit_author_address
'Arpan Hazra'
;Stellenbosch University
South Africa
;
_audit_update_record             
;
2019-08-01 deposited with the CCDC.	2019-09-06 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            'C37 H24 N2 O10 Zn2'
_chemical_formula_weight         787.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'

_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+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   10.899(3)
_cell_length_b                   16.264(5)
_cell_length_c                   10.897(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.332(7)
_cell_angle_gamma                90
_cell_volume                     1871.5(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1960
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      25.33

_exptl_crystal_description       block
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.012
_exptl_crystal_size_mid          0.007
_exptl_crystal_size_min          0.005
_exptl_absorpt_coefficient_mu    1.338
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   EMPIRICAL
_exptl_absorpt_correction_T_min  0.9587
_exptl_absorpt_correction_T_max  0.9835
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16299
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.300
_diffrn_reflns_theta_max         25.454
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3589
_reflns_number_gt                2731
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT  A'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0682P)²+2.1383P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   NOREF
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3589
_refine_ls_number_parameters     366
_refine_ls_number_restraints     66
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1331
_refine_ls_wR_factor_gt          0.1170
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.036
_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 0.30859(8) 0.34134(3) 0.27607(8) 0.03061(18) Uani 1 1 d . . . . .
O1 O 0.4956(5) 0.3178(3) 0.2937(7) 0.0620(18) Uani 1 1 d . . . . .
O2 O 1.1223(6) 0.3171(3) 0.2562(7) 0.057(2) Uani 1 1 d . . . . .
O3 O 0.3264(6) 0.3181(4) 0.4629(5) 0.080(2) Uani 1 1 d . . . . .
O4 O 0.2836(7) 0.3174(3) 1.0883(6) 0.064(2) Uani 1 1 d . . . . .
C1 C 0.5450(10) 0.250000 0.2839(10) 0.035(2) Uani 1 2 d S T P A .
C2 C 0.6761(9) 0.250000 0.2645(10) 0.038(2) Uani 1 2 d S T P . .
C3 C 0.7577(17) 0.1929(11) 0.3215(19) 0.049(5) Uani 0.5 1 d . . P A -1
H3 H 0.730958 0.152048 0.368763 0.059 Uiso 0.5 1 calc R U P A -1
C4 C 0.8812(16) 0.1933(9) 0.3117(17) 0.053(4) Uani 0.5 1 d . . P A -1
H4 H 0.935344 0.152316 0.353207 0.063 Uiso 0.5 1 calc R U P A -1
C5 C 0.9277(10) 0.250000 0.2451(11) 0.042(3) Uani 1 2 d S T P . .
C6 C 0.8420(14) 0.3110(9) 0.1765(15) 0.044(4) Uani 0.5 1 d . . P A -1
C7 C 0.7162(11) 0.3113(16) 0.1892(12) 0.036(5) Uani 0.5 1 d . . P A -1
C8 C 0.6213(16) 0.3681(13) 0.107(2) 0.081(6) Uani 0.5 1 d . . P A -1
H8 H 0.535787 0.364688 0.105327 0.097 Uiso 0.5 1 calc R U P A -1
C9 C 0.6608(16) 0.4217(13) 0.0373(19) 0.095(8) Uani 0.5 1 d . . P A -1
H9 H 0.603703 0.460999 -0.004883 0.114 Uiso 0.5 1 calc R U P A -1
C10 C 0.7830(19) 0.4238(13) 0.023(2) 0.098(8) Uani 0.5 1 d . . P A -1
H10 H 0.803542 0.460697 -0.034441 0.118 Uiso 0.5 1 calc R U P A -1
C11 C 0.8773(15) 0.3709(11) 0.0928(17) 0.066(5) Uani 0.5 1 d . . P A -1
H11 H 0.960339 0.374362 0.085492 0.080 Uiso 0.5 1 calc R U P A -1
C12 C 1.0689(9) 0.250000 0.2524(9) 0.038(2) Uani 1 2 d S T P A .
C13 C 0.3176(10) 0.250000 0.5126(10) 0.046(3) Uani 1 2 d S T P B .
C14 C 0.2964(10) 0.250000 0.6421(9) 0.035(2) Uani 1 2 d S T P . .
C15 C 0.335(2) 0.1817(11) 0.724(2) 0.052(5) Uani 0.5 1 d . . P B -1
H15 H 0.366927 0.134481 0.695503 0.062 Uiso 0.5 1 calc R U P B -1
C16 C 0.323(2) 0.1868(12) 0.8497(19) 0.053(5) Uani 0.5 1 d . . P B -1
H16 H 0.349977 0.142003 0.902609 0.064 Uiso 0.5 1 calc R U P B -1
C17 C 0.2774(9) 0.250000 0.8966(9) 0.035(2) Uani 1 2 d S T P . .
C18 C 0.237(2) 0.3219(9) 0.8133(16) 0.037(4) Uani 0.5 1 d . . P B -1
C19 C 0.250(2) 0.3183(13) 0.689(2) 0.045(5) Uani 0.5 1 d . U P B -1
C20 C 0.1925(16) 0.3870(9) 0.6066(16) 0.056(4) Uani 0.5 1 d . . P B -1
H20 H 0.188143 0.382219 0.520556 0.067 Uiso 0.5 1 calc R U P B -1
C21 C 0.1459(15) 0.4554(9) 0.6452(14) 0.053(4) Uani 0.5 1 d . . P B -1
H21 H 0.122303 0.500148 0.591501 0.064 Uiso 0.5 1 calc R U P B -1
C22 C 0.1346(16) 0.4567(9) 0.7649(18) 0.070(5) Uani 0.5 1 d . . P B -1
H22 H 0.095516 0.502128 0.790631 0.083 Uiso 0.5 1 calc R U P B -1
C23 C 0.1776(14) 0.3947(9) 0.8537(13) 0.045(4) Uani 0.5 1 d . . P B -1
H23 H 0.168912 0.399387 0.936177 0.054 Uiso 0.5 1 calc R U P B -1
C24 C 0.2777(10) 0.250000 1.0336(10) 0.039(2) Uani 1 2 d S T P B .
C25 C 0.3299(16) 0.5154(6) 0.3820(8) 0.063(5) Uani 0.5 1 d G U P C -1
H25 H 0.329049 0.488414 0.457092 0.075 Uiso 0.5 1 calc R U P C -1
C26 C 0.3383(16) 0.6006(6) 0.3799(9) 0.074(9) Uani 0.5 1 d G U P C -1
H26 H 0.343056 0.630693 0.453540 0.088 Uiso 0.5 1 calc R U P C -1
C27 C 0.3395(14) 0.6409(4) 0.2678(12) 0.052(5) Uani 0.5 1 d G U P C -1
C28 C 0.3324(13) 0.5960(5) 0.1577(10) 0.071(6) Uani 0.5 1 d G U P C -1
H28 H 0.333246 0.622940 0.082665 0.085 Uiso 0.5 1 calc R U P C -1
C29 C 0.3240(13) 0.5107(5) 0.1598(9) 0.071(6) Uani 0.5 1 d G U P C -1
H29 H 0.319240 0.480662 0.086215 0.085 Uiso 0.5 1 calc R U P C -1
N1 N 0.3228(14) 0.4704(4) 0.2720(10) 0.030(5) Uani 0.5 1 d G . P C -1
C30 C 0.3371(16) 0.7336(6) 0.2482(16) 0.065(3) Uani 0.5 1 d . . P C -1
H30A H 0.265619 0.748124 0.178962 0.078 Uiso 0.5 1 calc R U P C -1
H30B H 0.413891 0.750631 0.225353 0.078 Uiso 0.5 1 calc R U P C -1
C32 C 0.4144(15) 0.9993(8) 0.3242(19) 0.056(4) Uani 0.5 1 d . . P C -1
H32 H 0.487927 1.028688 0.325448 0.067 Uiso 0.5 1 calc R U P C -1
C33 C 0.4227(19) 0.9146(9) 0.3462(19) 0.064(5) Uani 0.5 1 d . U P C -1
H33 H 0.500871 0.888167 0.364850 0.077 Uiso 0.5 1 calc R U P C -1
C35 C 0.2066(17) 0.9143(8) 0.3203(17) 0.062(5) Uani 0.5 1 d . . P C -1
H35 H 0.131696 0.887191 0.321209 0.074 Uiso 0.5 1 calc R U P C -1
C36 C 0.2098(15) 0.9966(9) 0.2993(16) 0.051(5) Uani 0.5 1 d . . P C -1
H36 H 0.132888 1.024469 0.281100 0.061 Uiso 0.5 1 calc R U P C -1
C31 C 0.3268(16) 0.7790(6) 0.3683(16) 0.065(3) Uani 0.5 1 d . . P C -1
H31A H 0.399971 0.766821 0.437083 0.078 Uiso 0.5 1 calc R U P C -1
H31B H 0.251413 0.761252 0.393118 0.078 Uiso 0.5 1 calc R U P C -1
C34 C 0.320(2) 0.8736(12) 0.340(2) 0.056(5) Uani 0.5 1 d . . P C -1
N2 N 0.3072(19) 1.0383(8) 0.3021(17) 0.035(4) Uani 0.5 1 d . U P C -1
O5 O 1.007679 0.066460 0.008420 0.175(8) Uani 0.5 1 d . U P D -1
O6 O 0.979109 0.196140 -0.076779 0.189(9) Uani 0.5 1 d . U P D -1
C37 C 0.985459 0.129890 -0.036039 0.138(10) Uani 0.5 1 d . U P D -1


_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 2.027(6) 1_455 ?
Zn1 O3 2.032(5) . ?
Zn1 O4 2.034(6) 1_554 ?
Zn1 O1 2.035(5) . ?
Zn1 N1 2.107(6) . ?
Zn1 Zn1 2.9710(13) 4_565 ?
O1 C1 1.243(6) . ?
O2 C12 1.233(6) . ?
O3 C13 1.247(7) . ?
O4 C24 1.243(7) . ?
C1 C2 1.495(13) . ?
C2 C3 1.329(18) . ?
C2 C7 1.43(2) . ?
C3 C4 1.38(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.348(17) . ?
C4 H4 0.9300 . ?
C5 C6 1.440(17) . ?
C5 C12 1.521(13) . ?
C6 C7 1.411(17) . ?
C6 C11 1.45(2) . ?
C7 C8 1.51(2) . ?
C8 C9 1.29(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.38(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.41(2) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C13 C14 1.486(13) . ?
C14 C19 1.37(2) . ?
C14 C15 1.424(19) . ?
C15 C16 1.41(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.301(19) . ?
C16 H16 0.9300 . ?
C17 C18 1.479(18) . ?
C17 C24 1.492(13) . ?
C18 C19 1.40(3) . ?
C18 C23 1.47(2) . ?
C19 C20 1.48(2) . ?
C20 C21 1.33(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.34(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.40(2) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C25 C26 1.3900 . ?
C25 N1 1.3900 . ?
C25 H25 0.9300 . ?
C26 C27 1.3900 . ?
C26 H26 0.9300 . ?
C27 C28 1.3900 . ?
C27 C30 1.522(11) . ?
C28 C29 1.3900 . ?
C28 H28 0.9300 . ?
C29 N1 1.3900 . ?
C29 H29 0.9300 . ?
C30 C31 1.531(19) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C32 N2 1.30(2) . ?
C32 C33 1.40(2) . ?
C32 H32 0.9300 . ?
C33 C34 1.29(3) . ?
C33 H33 0.9300 . ?
C35 C36 1.360(19) . ?
C35 C34 1.37(3) . ?
C35 H35 0.9300 . ?
C36 N2 1.25(2) . ?
C36 H36 0.9300 . ?
C31 C34 1.57(2) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
O5 C37 1.1400(3) . ?
O6 C37 1.1609(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Zn1 O3 85.1(2) 1_455 . ?
O2 Zn1 O4 88.5(2) 1_455 1_554 ?
O3 Zn1 O4 158.2(2) . 1_554 ?
O2 Zn1 O1 157.94(19) 1_455 . ?
O3 Zn1 O1 91.5(2) . . ?
O4 Zn1 O1 86.6(2) 1_554 . ?
O2 Zn1 N1 105.6(4) 1_455 . ?
O3 Zn1 N1 102.5(3) . . ?
O4 Zn1 N1 99.3(3) 1_554 . ?
O1 Zn1 N1 96.5(4) . . ?
O2 Zn1 Zn1 78.79(14) 1_455 4_565 ?
O3 Zn1 Zn1 79.3(2) . 4_565 ?
O4 Zn1 Zn1 78.98(14) 1_554 4_565 ?
O1 Zn1 Zn1 79.15(14) . 4_565 ?
N1 Zn1 Zn1 175.3(4) . 4_565 ?
C1 O1 Zn1 127.1(6) . . ?
C12 O2 Zn1 128.9(6) . 1_655 ?
C13 O3 Zn1 127.0(6) . . ?
C24 O4 Zn1 129.0(6) . 1_556 ?
O1 C1 O1 124.9(9) . 4_565 ?
O1 C1 C2 117.5(5) . . ?
O1 C1 C2 117.5(5) 4_565 . ?
C3 C2 C7 119.5(12) . . ?
C3 C2 C1 119.1(10) . . ?
C7 C2 C1 121.4(8) . . ?
C2 C3 C4 121.0(15) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 123.4(14) . . ?
C5 C4 H4 118.3 . . ?
C3 C4 H4 118.3 . . ?
C4 C5 C6 118.0(12) . . ?
C4 C5 C12 118.8(10) . . ?
C6 C5 C12 123.0(8) . . ?
C7 C6 C5 118.2(14) . . ?
C7 C6 C11 118.4(15) . . ?
C5 C6 C11 123.4(13) . . ?
C6 C7 C2 119.8(15) . . ?
C6 C7 C8 118.9(15) . . ?
C2 C7 C8 120.6(11) . . ?
C9 C8 C7 118.8(15) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 123.6(17) . . ?
C8 C9 H9 118.2 . . ?
C10 C9 H9 118.2 . . ?
C9 C10 C11 121.0(15) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C10 C11 C6 118.7(14) . . ?
C10 C11 H11 120.7 . . ?
C6 C11 H11 120.7 . . ?
O2 C12 O2 124.6(10) . 4_565 ?
O2 C12 C5 117.7(5) . . ?
O2 C12 C5 117.7(5) 4_565 . ?
O3 C13 O3 125.3(10) 4_565 . ?
O3 C13 C14 117.3(5) 4_565 . ?
O3 C13 C14 117.3(5) . . ?
C19 C14 C15 118.3(11) . . ?
C19 C14 C13 121.0(9) . . ?
C15 C14 C13 120.5(9) . . ?
C16 C15 C14 118.9(16) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C17 C16 C15 124.3(17) . . ?
C17 C16 H16 117.8 . . ?
C15 C16 H16 117.8 . . ?
C16 C17 C18 118.0(12) . . ?
C16 C17 C24 119.1(10) . . ?
C18 C17 C24 122.6(8) . . ?
C19 C18 C23 119.0(16) . . ?
C19 C18 C17 118.2(15) . . ?
C23 C18 C17 122.8(14) . . ?
C14 C19 C18 122.3(16) . . ?
C14 C19 C20 121.6(16) . . ?
C18 C19 C20 115.3(18) . . ?
C21 C20 C19 125.2(16) . . ?
C21 C20 H20 117.4 . . ?
C19 C20 H20 117.4 . . ?
C20 C21 C22 117.1(14) . . ?
C20 C21 H21 121.5 . . ?
C22 C21 H21 121.5 . . ?
C21 C22 C23 124.5(13) . . ?
C21 C22 H22 117.7 . . ?
C23 C22 H22 117.7 . . ?
C22 C23 C18 118.2(13) . . ?
C22 C23 H23 120.9 . . ?
C18 C23 H23 120.9 . . ?
O4 C24 O4 124.0(10) 4_565 . ?
O4 C24 C17 117.9(5) 4_565 . ?
O4 C24 C17 117.9(5) . . ?
C26 C25 N1 120.0 . . ?
C26 C25 H25 120.0 . . ?
N1 C25 H25 120.0 . . ?
C25 C26 C27 120.0 . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C28 C27 C26 120.0 . . ?
C28 C27 C30 113.9(10) . . ?
C26 C27 C30 125.9(10) . . ?
C27 C28 C29 120.0 . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C28 C29 N1 120.0 . . ?
C28 C29 H29 120.0 . . ?
N1 C29 H29 120.0 . . ?
C29 N1 C25 120.0 . . ?
C29 N1 Zn1 120.3(5) . . ?
C25 N1 Zn1 119.7(5) . . ?
C27 C30 C31 111.1(10) . . ?
C27 C30 H30A 109.4 . . ?
C31 C30 H30A 109.4 . . ?
C27 C30 H30B 109.4 . . ?
C31 C30 H30B 109.4 . . ?
H30A C30 H30B 108.0 . . ?
N2 C32 C33 122.0(17) . . ?
N2 C32 H32 119.0 . . ?
C33 C32 H32 119.0 . . ?
C34 C33 C32 118.7(18) . . ?
C34 C33 H33 120.6 . . ?
C32 C33 H33 120.6 . . ?
C36 C35 C34 116.3(16) . . ?
C36 C35 H35 121.9 . . ?
C34 C35 H35 121.9 . . ?
N2 C36 C35 125.8(16) . . ?
N2 C36 H36 117.1 . . ?
C35 C36 H36 117.1 . . ?
C30 C31 C34 108.4(12) . . ?
C30 C31 H31A 110.0 . . ?
C34 C31 H31A 110.0 . . ?
C30 C31 H31B 110.0 . . ?
C34 C31 H31B 110.0 . . ?
H31A C31 H31B 108.4 . . ?
C33 C34 C35 119.7(19) . . ?
C33 C34 C31 119.7(19) . . ?
C35 C34 C31 120.3(18) . . ?
C36 N2 C32 117.3(13) . . ?
O5 C37 O6 171.401(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 O1 C1 O1 -19.5(17) . . . 4_565 ?
Zn1 O1 C1 C2 163.4(7) . . . . ?
O1 C1 C2 C3 141.8(13) . . . . ?
O1 C1 C2 C3 -35.6(17) 4_565 . . . ?
O1 C1 C2 C7 -36.4(17) . . . . ?
O1 C1 C2 C7 146.2(12) 4_565 . . . ?
C7 C2 C3 C4 2(3) . . . . ?
C1 C2 C3 C4 -176.5(15) . . . . ?
C2 C3 C4 C5 0(3) . . . . ?
C3 C4 C5 C6 -3(3) . . . . ?
C3 C4 C5 C12 173.5(16) . . . . ?
C4 C5 C6 C7 4(2) . . . . ?
C12 C5 C6 C7 -172.1(13) . . . . ?
C4 C5 C6 C11 -174.5(16) . . . . ?
C12 C5 C6 C11 9(2) . . . . ?
C5 C6 C7 C2 -2(3) . . . . ?
C11 C6 C7 C2 176.1(16) . . . . ?
C5 C6 C7 C8 -172.9(17) . . . . ?
C11 C6 C7 C8 6(3) . . . . ?
C3 C2 C7 C6 0(3) . . . . ?
C1 C2 C7 C6 177.9(13) . . . . ?
C3 C2 C7 C8 169.9(17) . . . . ?
C1 C2 C7 C8 -12(2) . . . . ?
C6 C7 C8 C9 -8(3) . . . . ?
C2 C7 C8 C9 -178(2) . . . . ?
C7 C8 C9 C10 8(4) . . . . ?
C8 C9 C10 C11 -6(4) . . . . ?
C9 C10 C11 C6 3(3) . . . . ?
C7 C6 C11 C10 -3(3) . . . . ?
C5 C6 C11 C10 175.1(18) . . . . ?
Zn1 O2 C12 O2 -2.6(16) 1_655 . . 4_565 ?
Zn1 O2 C12 C5 176.2(7) 1_655 . . . ?
C4 C5 C12 O2 -140.8(12) . . . . ?
C6 C5 C12 O2 35.2(16) . . . . ?
C4 C5 C12 O2 38.1(15) . . . 4_565 ?
C6 C5 C12 O2 -145.9(11) . . . 4_565 ?
Zn1 O3 C13 O3 18.2(18) . . . 4_565 ?
Zn1 O3 C13 C14 -162.5(7) . . . . ?
O3 C13 C14 C19 -161.3(16) 4_565 . . . ?
O3 C13 C14 C19 19(2) . . . . ?
O3 C13 C14 C15 24.8(18) 4_565 . . . ?
O3 C13 C14 C15 -154.6(13) . . . . ?
C19 C14 C15 C16 0(3) . . . . ?
C13 C14 C15 C16 174.6(15) . . . . ?
C14 C15 C16 C17 1(3) . . . . ?
C15 C16 C17 C18 -1(3) . . . . ?
C15 C16 C17 C24 -176.1(16) . . . . ?
C16 C17 C18 C19 -1(3) . . . . ?
C24 C17 C18 C19 174.4(17) . . . . ?
C16 C17 C18 C23 176.7(17) . . . . ?
C24 C17 C18 C23 -8(2) . . . . ?
C15 C14 C19 C18 -2(4) . . . . ?
C13 C14 C19 C18 -176.1(19) . . . . ?
C15 C14 C19 C20 -171.4(15) . . . . ?
C13 C14 C19 C20 15(3) . . . . ?
C23 C18 C19 C14 -175.2(17) . . . . ?
C17 C18 C19 C14 2(4) . . . . ?
C23 C18 C19 C20 -5(3) . . . . ?
C17 C18 C19 C20 172.1(15) . . . . ?
C14 C19 C20 C21 -179.9(19) . . . . ?
C18 C19 C20 C21 10(3) . . . . ?
C19 C20 C21 C22 -10(3) . . . . ?
C20 C21 C22 C23 5(3) . . . . ?
C21 C22 C23 C18 -1(3) . . . . ?
C19 C18 C23 C22 2(3) . . . . ?
C17 C18 C23 C22 -175.7(16) . . . . ?
Zn1 O4 C24 O4 1.8(18) 1_556 . . 4_565 ?
Zn1 O4 C24 C17 -171.4(6) 1_556 . . . ?
C16 C17 C24 O4 -22.0(18) . . . 4_565 ?
C18 C17 C24 O4 163.0(13) . . . 4_565 ?
C16 C17 C24 O4 151.6(14) . . . . ?
C18 C17 C24 O4 -23.4(17) . . . . ?
N1 C25 C26 C27 0.0 . . . . ?
C25 C26 C27 C28 0.0 . . . . ?
C25 C26 C27 C30 174.5(14) . . . . ?
C26 C27 C28 C29 0.0 . . . . ?
C30 C27 C28 C29 -175.2(13) . . . . ?
C27 C28 C29 N1 0.0 . . . . ?
C28 C29 N1 C25 0.0 . . . . ?
C28 C29 N1 Zn1 179.5(10) . . . . ?
C26 C25 N1 C29 0.0 . . . . ?
C26 C25 N1 Zn1 -179.5(10) . . . . ?
C28 C27 C30 C31 172.2(11) . . . . ?
C26 C27 C30 C31 -2.7(18) . . . . ?
N2 C32 C33 C34 2(3) . . . . ?
C34 C35 C36 N2 -3(3) . . . . ?
C27 C30 C31 C34 -177.9(14) . . . . ?
C32 C33 C34 C35 -4(3) . . . . ?
C32 C33 C34 C31 -178.2(18) . . . . ?
C36 C35 C34 C33 4(3) . . . . ?
C36 C35 C34 C31 178.6(16) . . . . ?
C30 C31 C34 C33 -82(2) . . . . ?
C30 C31 C34 C35 104(2) . . . . ?
C35 C36 N2 C32 2(3) . . . . ?
C33 C32 N2 C36 -1(3) . . . . ?

_refine_diff_density_max         0.696
_refine_diff_density_min         -0.782
_refine_diff_density_rms         0.100


_chemical_properties_physical    Heat-sensitive
