# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1956330'
loop_
_audit_author_name
_audit_author_address
'Sanchari Dasgupta'
;University of calcutta
India
;
_audit_update_record             
;
2019-09-27 deposited with the CCDC.	2019-12-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H13 Cl2 N3 O2 Zn,2(H2O)'
_chemical_formula_sum            'C14 H17 Cl2 N3 O4 Zn'
_chemical_formula_weight         427.60

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.4922(15)
_cell_length_b                   9.5414(15)
_cell_length_c                   9.7672(15)
_cell_angle_alpha                96.308(3)
_cell_angle_beta                 92.175(3)
_cell_angle_gamma                95.542(3)
_cell_volume                     874.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9136
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      33.11

_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_F_000             422
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    1.727
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35787
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.158
_diffrn_reflns_theta_max         33.648
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6517
_reflns_number_gt                5221
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0391P)²+0.2616P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0234(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6517
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0301
_refine_ls_wR_factor_ref         0.0822
_refine_ls_wR_factor_gt          0.0754
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.002
_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 0.67580(2) 0.70697(2) 0.18544(2) 0.03388(6) Uani 1 1 d . . . . .
Cl1 Cl 0.86011(4) 0.74325(4) 0.33951(4) 0.04033(9) Uani 1 1 d . . . . .
Cl2 Cl 0.65511(5) 0.87550(5) 0.04743(5) 0.05166(11) Uani 1 1 d . . . . .
O3 O 0.33034(16) 0.28320(13) 0.38927(16) 0.0550(3) Uani 1 1 d G . . . .
H3B H 0.269103 0.262782 0.447152 0.082 Uiso 1 1 d G U . . .
H3C H 0.349074 0.203366 0.350603 0.082 Uiso 1 1 d G U . . .
O2 O 0.50447(12) 0.77767(11) 0.32454(12) 0.0393(2) Uani 1 1 d . . . . .
O4 O 0.4089(3) 0.0423(2) 0.25062(16) 0.0843(6) Uani 1 1 d G . . . .
H4A H 0.451609 -0.027668 0.270479 0.126 Uiso 1 1 d G U . . .
H4B H 0.412391 0.048738 0.164681 0.126 Uiso 1 1 d G U . . .
N1 N 0.73295(13) 0.53320(13) 0.04010(13) 0.0355(2) Uani 1 1 d . . . . .
N2 N 0.54830(12) 0.52695(12) 0.22894(12) 0.0314(2) Uani 1 1 d . . . . .
N3 N 0.45166(13) 0.54339(13) 0.32714(13) 0.0346(2) Uani 1 1 d . . . . .
H3 H 0.411(2) 0.474(2) 0.354(2) 0.041 Uiso 1 1 d . U . . .
O1 O 0.01030(14) 0.77971(13) 0.74542(15) 0.0548(3) Uani 1 1 d . . . . .
C1 C 0.82341(18) 0.5397(2) -0.06107(17) 0.0450(4) Uani 1 1 d . . . . .
H1 H 0.859381 0.628193 -0.082924 0.054 Uiso 1 1 calc R U . . .
C2 C 0.8655(2) 0.4202(2) -0.13437(19) 0.0521(4) Uani 1 1 d . . . . .
H2 H 0.928319 0.428396 -0.204528 0.063 Uiso 1 1 calc R U . . .
C3 C 0.8140(2) 0.2898(2) -0.1028(2) 0.0533(4) Uani 1 1 d . . . . .
H3A H 0.842370 0.208265 -0.150385 0.064 Uiso 1 1 calc R U . . .
C4 C 0.71853(19) 0.27991(18) 0.00133(19) 0.0459(4) Uani 1 1 d . . . . .
H4 H 0.681618 0.192271 0.024609 0.055 Uiso 1 1 calc R U . . .
C5 C 0.68043(15) 0.40452(15) 0.06893(15) 0.0342(3) Uani 1 1 d . . . . .
C6 C 0.57637(16) 0.40490(15) 0.17639(16) 0.0368(3) Uani 1 1 d . . . . .
H6 H 0.533650 0.321582 0.204365 0.044 Uiso 1 1 calc R U . . .
C7 C 0.43141(14) 0.68056(14) 0.37022(14) 0.0311(2) Uani 1 1 d . . . . .
C8 C 0.32111(14) 0.70519(14) 0.46912(14) 0.0312(2) Uani 1 1 d . . . . .
C9 C 0.23357(19) 0.59655(16) 0.51440(19) 0.0441(4) Uani 1 1 d . . . . .
H9 H 0.244007 0.502943 0.482008 0.053 Uiso 1 1 calc R U . . .
C10 C 0.13173(19) 0.62559(17) 0.6065(2) 0.0478(4) Uani 1 1 d . . . . .
H10 H 0.074415 0.551543 0.636548 0.057 Uiso 1 1 calc R U . . .
C11 C 0.11367(16) 0.76399(16) 0.65482(16) 0.0376(3) Uani 1 1 d . . . . .
C12 C 0.1988(2) 0.87375(17) 0.6104(2) 0.0513(4) Uani 1 1 d . . . . .
H12 H 0.186842 0.967250 0.641844 0.062 Uiso 1 1 calc R U . . .
C13 C 0.30231(19) 0.84339(17) 0.5186(2) 0.0474(4) Uani 1 1 d . . . . .
H13 H 0.360440 0.917452 0.489577 0.057 Uiso 1 1 calc R U . . .
C14 C -0.0213(3) 0.9205(2) 0.7895(3) 0.0730(7) Uani 1 1 d . . . . .
H14A H 0.059465 0.972197 0.840313 0.110 Uiso 1 1 calc R U . . .
H14B H -0.100753 0.916877 0.847492 0.110 Uiso 1 1 calc R U . . .
H14C H -0.043960 0.967102 0.710454 0.110 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N2 2.0961(12) . ?
Zn1 N1 2.1849(12) . ?
Zn1 Cl2 2.2267(5) . ?
Zn1 Cl1 2.2392(5) . ?
Zn1 O2 2.2636(11) . ?
O3 H3B 0.8501 . ?
O3 H3C 0.8500 . ?
O2 C7 1.2363(17) . ?
O4 H4A 0.8499 . ?
O4 H4B 0.8500 . ?
N1 C1 1.3361(19) . ?
N1 C5 1.3430(19) . ?
N2 C6 1.2766(18) . ?
N2 N3 1.3592(15) . ?
N3 C7 1.3640(18) . ?
N3 H3 0.81(2) . ?
O1 C11 1.3541(17) . ?
O1 C14 1.429(2) . ?
C1 C2 1.379(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.363(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(2) . ?
C3 H3A 0.9300 . ?
C4 C5 1.382(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.4684(19) . ?
C6 H6 0.9300 . ?
C7 C8 1.4694(18) . ?
C8 C13 1.384(2) . ?
C8 C9 1.387(2) . ?
C9 C10 1.372(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.382(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.379(2) . ?
C12 C13 1.385(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Zn1 N1 74.55(5) . . ?
N2 Zn1 Cl2 135.52(4) . . ?
N1 Zn1 Cl2 101.29(4) . . ?
N2 Zn1 Cl1 107.78(4) . . ?
N1 Zn1 Cl1 103.09(4) . . ?
Cl2 Zn1 Cl1 116.112(19) . . ?
N2 Zn1 O2 71.45(4) . . ?
N1 Zn1 O2 143.74(4) . . ?
Cl2 Zn1 O2 94.27(3) . . ?
Cl1 Zn1 O2 98.93(4) . . ?
H3B O3 H3C 104.5 . . ?
C7 O2 Zn1 114.87(9) . . ?
H4A O4 H4B 109.5 . . ?
C1 N1 C5 117.93(13) . . ?
C1 N1 Zn1 127.98(11) . . ?
C5 N1 Zn1 113.65(9) . . ?
C6 N2 N3 122.12(12) . . ?
C6 N2 Zn1 119.01(10) . . ?
N3 N2 Zn1 118.21(9) . . ?
C7 N3 N2 114.90(12) . . ?
C7 N3 H3 125.9(14) . . ?
N2 N3 H3 119.2(14) . . ?
C11 O1 C14 117.64(14) . . ?
N1 C1 C2 122.55(17) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C3 C2 C1 119.24(16) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 119.43(15) . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 H3A 120.3 . . ?
C5 C4 C3 117.82(16) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 H4 121.1 . . ?
N1 C5 C4 123.00(14) . . ?
N1 C5 C6 115.16(12) . . ?
C4 C5 C6 121.83(14) . . ?
N2 C6 C5 115.69(13) . . ?
N2 C6 H6 122.2 . . ?
C5 C6 H6 122.2 . . ?
O2 C7 N3 119.41(12) . . ?
O2 C7 C8 123.07(12) . . ?
N3 C7 C8 117.51(12) . . ?
C13 C8 C9 118.22(13) . . ?
C13 C8 C7 118.62(13) . . ?
C9 C8 C7 123.16(12) . . ?
C10 C9 C8 120.74(14) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 120.51(14) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
O1 C11 C12 124.97(14) . . ?
O1 C11 C10 115.28(14) . . ?
C12 C11 C10 119.75(13) . . ?
C11 C12 C13 119.34(14) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C8 C13 C12 121.43(14) . . ?
C8 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
C6 N2 N3 C7 -178.47(14) . . . . ?
Zn1 N2 N3 C7 10.92(16) . . . . ?
C5 N1 C1 C2 -1.0(3) . . . . ?
Zn1 N1 C1 C2 170.96(14) . . . . ?
N1 C1 C2 C3 -0.3(3) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C1 N1 C5 C4 1.7(2) . . . . ?
Zn1 N1 C5 C4 -171.36(13) . . . . ?
C1 N1 C5 C6 -177.10(15) . . . . ?
Zn1 N1 C5 C6 9.85(17) . . . . ?
C3 C4 C5 N1 -1.1(3) . . . . ?
C3 C4 C5 C6 177.59(16) . . . . ?
N3 N2 C6 C5 178.46(13) . . . . ?
Zn1 N2 C6 C5 -11.00(19) . . . . ?
N1 C5 C6 N2 0.2(2) . . . . ?
C4 C5 C6 N2 -178.65(15) . . . . ?
Zn1 O2 C7 N3 -4.64(18) . . . . ?
Zn1 O2 C7 C8 175.95(10) . . . . ?
N2 N3 C7 O2 -3.6(2) . . . . ?
N2 N3 C7 C8 175.81(12) . . . . ?
O2 C7 C8 C13 -3.1(2) . . . . ?
N3 C7 C8 C13 177.47(15) . . . . ?
O2 C7 C8 C9 176.17(16) . . . . ?
N3 C7 C8 C9 -3.2(2) . . . . ?
C13 C8 C9 C10 -0.4(3) . . . . ?
C7 C8 C9 C10 -179.69(17) . . . . ?
C8 C9 C10 C11 0.6(3) . . . . ?
C14 O1 C11 C12 5.6(3) . . . . ?
C14 O1 C11 C10 -174.7(2) . . . . ?
C9 C10 C11 O1 -179.84(18) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
O1 C11 C12 C13 179.14(18) . . . . ?
C10 C11 C12 C13 -0.6(3) . . . . ?
C9 C8 C13 C12 -0.3(3) . . . . ?
C7 C8 C13 C12 179.03(18) . . . . ?
C11 C12 C13 C8 0.8(3) . . . . ?

_refine_diff_density_max         0.471
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.100

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1956331'
loop_
_audit_author_name
_audit_author_address
'Sanchari Dasgupta'
;University of calcutta
India
;
_audit_update_record             
;
2019-09-27 deposited with the CCDC.	2019-12-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H17 Cl2 N3 O2 Zn'
_chemical_formula_sum            'C20 H17 Cl2 N3 O2 Zn'
_chemical_formula_weight         467.66

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'
Cl Cl 0.1484 0.1585 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   10.0765(8)
_cell_length_b                   11.2853(9)
_cell_length_c                   17.8222(14)
_cell_angle_alpha                90
_cell_angle_beta                 99.024(2)
_cell_angle_gamma                90
_cell_volume                     2001.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9041
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      26.74

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_F_000             1004
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    1.523
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            54481
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.144
_diffrn_reflns_theta_max         26.736
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4247
_reflns_number_gt                3593
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0761P)²+1.8778P] 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         4247
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.1042
_refine_ls_wR_factor_gt          0.0910
_refine_ls_goodness_of_fit_ref   0.859
_refine_ls_restrained_S_all      0.859
_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 0.73425(2) 0.60697(2) 0.58683(2) 0.03558(11) Uani 1 1 d . . . . .
Cl1 Cl 0.81376(6) 0.43019(6) 0.55559(4) 0.04560(16) Uani 1 1 d . . . . .
Cl2 Cl 0.86395(7) 0.71708(6) 0.67244(4) 0.05324(18) Uani 1 1 d . . . . .
O1 O 0.59096(16) 0.54410(19) 0.65681(10) 0.0494(5) Uani 1 1 d . . . . .
N2 N 0.43599(19) 0.63619(19) 0.57246(11) 0.0372(4) Uani 1 1 d . . . . .
H2 H 0.354574 0.658206 0.557039 0.045 Uiso 1 1 calc R U . . .
N3 N 0.54094(19) 0.66931(18) 0.53714(10) 0.0355(4) Uani 1 1 d . . . . .
N4 N 0.7609(2) 0.70183(19) 0.48682(12) 0.0407(4) Uani 1 1 d . . . . .
O2 O 0.0905(2) 0.3593(2) 0.79176(12) 0.0564(5) Uani 1 1 d . . . . .
C1 C 0.4713(2) 0.5652(2) 0.63432(12) 0.0347(5) Uani 1 1 d . . . . .
C2 C 0.5273(2) 0.7417(2) 0.48067(12) 0.0342(5) Uani 1 1 d . . . . .
C3 C 0.4052(2) 0.8097(2) 0.45112(13) 0.0361(5) Uani 1 1 d . . . . .
C4 C 0.3475(3) 0.8813(2) 0.50080(16) 0.0494(6) Uani 1 1 d . . . . .
H1 H 0.382557 0.881539 0.552284 0.059 Uiso 1 1 calc R U . . .
C5 C 0.2380(3) 0.9522(3) 0.4739(2) 0.0626(8) Uani 1 1 d . . . . .
H18 H 0.198944 0.999444 0.507231 0.075 Uiso 1 1 calc R U . . .
C6 C 0.1873(3) 0.9521(3) 0.3974(2) 0.0606(8) Uani 1 1 d . . . . .
H3 H 0.115859 1.001686 0.378903 0.073 Uiso 1 1 calc R U . . .
C7 C 0.2410(3) 0.8800(3) 0.34848(17) 0.0538(7) Uani 1 1 d . . . . .
H5 H 0.204385 0.879131 0.297231 0.065 Uiso 1 1 calc R U . . .
C8 C 0.3491(3) 0.8087(3) 0.37459(14) 0.0447(6) Uani 1 1 d . . . . .
H4 H 0.384957 0.759611 0.340954 0.054 Uiso 1 1 calc R U . . .
C9 C 0.6547(2) 0.7586(2) 0.44895(12) 0.0337(4) Uani 1 1 d . . . . .
C10 C 0.6665(3) 0.8266(2) 0.38580(15) 0.0444(6) Uani 1 1 d . . . . .
H6 H 0.592831 0.867534 0.360234 0.053 Uiso 1 1 calc R U . . .
C11 C 0.7907(3) 0.8326(2) 0.36136(15) 0.0490(6) Uani 1 1 d . . . . .
H7 H 0.800409 0.876317 0.318320 0.059 Uiso 1 1 calc R U . . .
C12 C 0.8978(3) 0.7745(2) 0.40048(16) 0.0506(6) Uani 1 1 d . . . . .
H8 H 0.981659 0.778147 0.384988 0.061 Uiso 1 1 calc R U . . .
C13 C 0.8794(3) 0.7105(3) 0.46318(17) 0.0519(7) Uani 1 1 d . . . . .
H9 H 0.952751 0.671318 0.490439 0.062 Uiso 1 1 calc R U . . .
C14 C 0.3655(2) 0.5168(2) 0.67335(12) 0.0318(4) Uani 1 1 d . . . . .
C15 C 0.4037(2) 0.4345(2) 0.73094(13) 0.0353(5) Uani 1 1 d . . . . .
H16 H 0.493560 0.412980 0.743270 0.042 Uiso 1 1 calc R U . . .
C16 C 0.3099(3) 0.3847(2) 0.76978(14) 0.0408(5) Uani 1 1 d . . . . .
H15 H 0.336816 0.330420 0.808455 0.049 Uiso 1 1 calc R U . . .
C17 C 0.1750(2) 0.4151(2) 0.75143(13) 0.0381(5) Uani 1 1 d . . . . .
C18 C -0.0504(3) 0.3847(3) 0.7734(2) 0.0636(8) Uani 1 1 d . . . . .
H10 H -0.065384 0.467426 0.781407 0.095 Uiso 1 1 calc R U . . .
H12 H -0.098787 0.338545 0.805450 0.095 Uiso 1 1 calc R U . . .
H11 H -0.081288 0.365048 0.721210 0.095 Uiso 1 1 calc R U . . .
C19 C 0.1352(2) 0.4982(2) 0.69502(13) 0.0410(5) Uani 1 1 d . . . . .
H13 H 0.045349 0.519805 0.683131 0.049 Uiso 1 1 calc R U . . .
C20 C 0.2302(2) 0.5487(2) 0.65649(13) 0.0383(5) Uani 1 1 d . . . . .
H14 H 0.203478 0.604630 0.618842 0.046 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N3 2.1289(19) . ?
Zn1 N4 2.132(2) . ?
Zn1 O1 2.1700(17) . ?
Zn1 Cl2 2.2259(7) . ?
Zn1 Cl1 2.2522(7) . ?
O1 C1 1.233(3) . ?
N2 C1 1.364(3) . ?
N2 N3 1.365(3) . ?
N2 H2 0.8600 . ?
N3 C2 1.287(3) . ?
N4 C13 1.330(3) . ?
N4 C9 1.336(3) . ?
O2 C17 1.353(3) . ?
O2 C18 1.435(4) . ?
C1 C14 1.466(3) . ?
C2 C3 1.475(3) . ?
C2 C9 1.494(3) . ?
C3 C4 1.391(4) . ?
C3 C8 1.392(3) . ?
C4 C5 1.386(4) . ?
C4 H1 0.9300 . ?
C5 C6 1.380(5) . ?
C5 H18 0.9300 . ?
C6 C7 1.365(5) . ?
C6 H3 0.9300 . ?
C7 C8 1.375(4) . ?
C7 H5 0.9300 . ?
C8 H4 0.9300 . ?
C9 C10 1.383(3) . ?
C10 C11 1.390(4) . ?
C10 H6 0.9300 . ?
C11 C12 1.359(4) . ?
C11 H7 0.9300 . ?
C12 C13 1.368(4) . ?
C12 H8 0.9300 . ?
C13 H9 0.9300 . ?
C14 C15 1.393(3) . ?
C14 C20 1.396(3) . ?
C15 C16 1.376(3) . ?
C15 H16 0.9300 . ?
C16 C17 1.390(4) . ?
C16 H15 0.9300 . ?
C17 C19 1.387(3) . ?
C18 H10 0.9600 . ?
C18 H12 0.9600 . ?
C18 H11 0.9600 . ?
C19 C20 1.385(3) . ?
C19 H13 0.9300 . ?
C20 H14 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
N3 Zn1 N4 73.35(7) . . ?
N3 Zn1 O1 72.50(7) . . ?
N4 Zn1 O1 145.81(7) . . ?
N3 Zn1 Cl2 120.08(6) . . ?
N4 Zn1 Cl2 98.93(6) . . ?
O1 Zn1 Cl2 99.24(6) . . ?
N3 Zn1 Cl1 121.85(6) . . ?
N4 Zn1 Cl1 98.15(6) . . ?
O1 Zn1 Cl1 98.45(6) . . ?
Cl2 Zn1 Cl1 118.07(3) . . ?
C1 O1 Zn1 117.07(15) . . ?
C1 N2 N3 114.26(18) . . ?
C1 N2 H2 122.9 . . ?
N3 N2 H2 122.9 . . ?
C2 N3 N2 122.64(19) . . ?
C2 N3 Zn1 120.89(15) . . ?
N2 N3 Zn1 116.25(14) . . ?
C13 N4 C9 119.5(2) . . ?
C13 N4 Zn1 122.58(18) . . ?
C9 N4 Zn1 117.85(15) . . ?
C17 O2 C18 118.0(2) . . ?
O1 C1 N2 119.6(2) . . ?
O1 C1 C14 121.4(2) . . ?
N2 C1 C14 119.02(19) . . ?
N3 C2 C3 126.1(2) . . ?
N3 C2 C9 112.6(2) . . ?
C3 C2 C9 121.13(19) . . ?
C4 C3 C8 118.8(2) . . ?
C4 C3 C2 118.9(2) . . ?
C8 C3 C2 122.2(2) . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 H1 119.8 . . ?
C3 C4 H1 119.8 . . ?
C6 C5 C4 119.5(3) . . ?
C6 C5 H18 120.2 . . ?
C4 C5 H18 120.2 . . ?
C7 C6 C5 120.6(3) . . ?
C7 C6 H3 119.7 . . ?
C5 C6 H3 119.7 . . ?
C6 C7 C8 120.4(3) . . ?
C6 C7 H5 119.8 . . ?
C8 C7 H5 119.8 . . ?
C7 C8 C3 120.3(3) . . ?
C7 C8 H4 119.8 . . ?
C3 C8 H4 119.8 . . ?
N4 C9 C10 120.9(2) . . ?
N4 C9 C2 114.56(19) . . ?
C10 C9 C2 124.5(2) . . ?
C9 C10 C11 118.6(2) . . ?
C9 C10 H6 120.7 . . ?
C11 C10 H6 120.7 . . ?
C12 C11 C10 119.9(2) . . ?
C12 C11 H7 120.1 . . ?
C10 C11 H7 120.1 . . ?
C11 C12 C13 118.4(2) . . ?
C11 C12 H8 120.8 . . ?
C13 C12 H8 120.8 . . ?
N4 C13 C12 122.7(3) . . ?
N4 C13 H9 118.6 . . ?
C12 C13 H9 118.6 . . ?
C15 C14 C20 118.5(2) . . ?
C15 C14 C1 117.40(19) . . ?
C20 C14 C1 124.1(2) . . ?
C16 C15 C14 120.7(2) . . ?
C16 C15 H16 119.6 . . ?
C14 C15 H16 119.6 . . ?
C15 C16 C17 120.2(2) . . ?
C15 C16 H15 119.9 . . ?
C17 C16 H15 119.9 . . ?
O2 C17 C19 124.4(2) . . ?
O2 C17 C16 115.7(2) . . ?
C19 C17 C16 119.9(2) . . ?
O2 C18 H10 109.5 . . ?
O2 C18 H12 109.5 . . ?
H10 C18 H12 109.5 . . ?
O2 C18 H11 109.5 . . ?
H10 C18 H11 109.5 . . ?
H12 C18 H11 109.5 . . ?
C20 C19 C17 119.6(2) . . ?
C20 C19 H13 120.2 . . ?
C17 C19 H13 120.2 . . ?
C19 C20 C14 121.0(2) . . ?
C19 C20 H14 119.5 . . ?
C14 C20 H14 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N2 N3 C2 -175.8(2) . . . . ?
C1 N2 N3 Zn1 -1.2(3) . . . . ?
Zn1 O1 C1 N2 -6.9(3) . . . . ?
Zn1 O1 C1 C14 174.01(16) . . . . ?
N3 N2 C1 O1 5.4(3) . . . . ?
N3 N2 C1 C14 -175.5(2) . . . . ?
N2 N3 C2 C3 7.4(4) . . . . ?
Zn1 N3 C2 C3 -166.92(18) . . . . ?
N2 N3 C2 C9 -176.6(2) . . . . ?
Zn1 N3 C2 C9 9.0(3) . . . . ?
N3 C2 C3 C4 54.6(3) . . . . ?
C9 C2 C3 C4 -121.1(3) . . . . ?
N3 C2 C3 C8 -128.3(3) . . . . ?
C9 C2 C3 C8 56.0(3) . . . . ?
C8 C3 C4 C5 -1.4(4) . . . . ?
C2 C3 C4 C5 175.8(3) . . . . ?
C3 C4 C5 C6 -0.6(5) . . . . ?
C4 C5 C6 C7 2.3(5) . . . . ?
C5 C6 C7 C8 -1.8(5) . . . . ?
C6 C7 C8 C3 -0.3(4) . . . . ?
C4 C3 C8 C7 1.9(4) . . . . ?
C2 C3 C8 C7 -175.2(2) . . . . ?
C13 N4 C9 C10 -0.3(4) . . . . ?
Zn1 N4 C9 C10 176.77(18) . . . . ?
C13 N4 C9 C2 179.7(2) . . . . ?
Zn1 N4 C9 C2 -3.2(3) . . . . ?
N3 C2 C9 N4 -3.6(3) . . . . ?
C3 C2 C9 N4 172.6(2) . . . . ?
N3 C2 C9 C10 176.5(2) . . . . ?
C3 C2 C9 C10 -7.4(4) . . . . ?
N4 C9 C10 C11 1.5(4) . . . . ?
C2 C9 C10 C11 -178.6(2) . . . . ?
C9 C10 C11 C12 -1.5(4) . . . . ?
C10 C11 C12 C13 0.5(4) . . . . ?
C9 N4 C13 C12 -0.8(4) . . . . ?
Zn1 N4 C13 C12 -177.8(2) . . . . ?
C11 C12 C13 N4 0.7(5) . . . . ?
O1 C1 C14 C15 -7.8(3) . . . . ?
N2 C1 C14 C15 173.1(2) . . . . ?
O1 C1 C14 C20 171.9(2) . . . . ?
N2 C1 C14 C20 -7.2(3) . . . . ?
C20 C14 C15 C16 0.7(3) . . . . ?
C1 C14 C15 C16 -179.6(2) . . . . ?
C14 C15 C16 C17 0.6(4) . . . . ?
C18 O2 C17 C19 2.1(4) . . . . ?
C18 O2 C17 C16 -178.0(3) . . . . ?
C15 C16 C17 O2 178.6(2) . . . . ?
C15 C16 C17 C19 -1.6(4) . . . . ?
O2 C17 C19 C20 -179.1(2) . . . . ?
C16 C17 C19 C20 1.1(4) . . . . ?
C17 C19 C20 C14 0.3(4) . . . . ?
C15 C14 C20 C19 -1.2(4) . . . . ?
C1 C14 C20 C19 179.1(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C19 H13 Cl2 0.93 2.87 3.660(3) 143.8 1_455
C13 H9 Cl1 0.93 2.85 3.538(3) 131.7 3_766
C13 H9 Cl1 0.93 2.85 3.538(3) 131.7 3_766
C19 H13 Cl2 0.93 2.87 3.660(3) 143.8 1_455
C13 H9 Cl1 0.93 2.85 3.538(3) 131.7 3_766
C19 H13 Cl2 0.93 2.87 3.660(3) 143.8 1_455
C13 H9 Cl1 0.93 2.85 3.538(3) 131.7 3_766
C19 H13 Cl2 0.93 2.87 3.660(3) 143.8 1_455
N2 H2 Cl1 0.86 2.61 3.209(2) 127.4 3_666
C13 H9 Cl1 0.93 2.85 3.538(3) 131.7 3_766
C19 H13 Cl2 0.93 2.87 3.660(3) 143.8 1_455

_refine_diff_density_max         0.278
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.088

