# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_smspzn_a
_database_code_depnum_ccdc_archive 'CCDC 2209945'
loop_
_audit_author_name
_audit_author_address
'Samit Pramanik'
;Jadavpur University
India
;
_audit_update_record             
;
2022-09-28 deposited with the CCDC.	2022-12-19 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         'C22 H20 N10 O2 Zn, 4(H2 O)'
_chemical_formula_sum            'C22 H28 N10 O6 Zn'
_chemical_formula_weight         593.93

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                   23.393(5)
_cell_length_b                   8.6036(19)
_cell_length_c                   13.597(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.497(7)
_cell_angle_gamma                90
_cell_volume                     2610.0(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296
_cell_measurement_reflns_used    2933
_cell_measurement_theta_min      1.826
_cell_measurement_theta_max      27.292

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_F_000             1232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.999
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.845
_exptl_absorpt_correction_T_max  0.923
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38455
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_av_R_equivalents  0.1199
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.826
_diffrn_reflns_theta_max         27.292
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2905
_reflns_number_gt                2274
_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       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'APEX2(Bruker,2007)and SAINT (Bruker,2007)'
_computing_data_reduction        'SAINT(Bruker,2007)and XPREP(Bruker,2007)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    
;    
ORTEP-3 for Windows (Farrugia, 1997), DIAMOND (Brandenburg,
1999) and Mercury (Macrae et al., 2006)
;
_computing_publication_material  'PLATON (Spek, 2009)'
_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)+(0.0511P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2933
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0880
_refine_ls_wR_factor_gt          0.0842
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_restrained_S_all      0.972
_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 0.92055(4) 0.750000 0.03330(12) Uani 1 2 d S T P . .
O1 O 0.44880(6) 0.75313(16) 0.63630(10) 0.0398(3) Uani 1 1 d . . . . .
N3 N 0.54187(7) 0.90161(17) 0.63409(12) 0.0319(3) Uani 1 1 d . . . . .
O2 O 0.32797(7) 0.2355(2) 0.14348(12) 0.0522(4) Uani 1 1 d G . . . .
H2A H 0.338194 0.288638 0.198747 0.078 Uiso 1 1 d G U . . .
H2B H 0.360788 0.215182 0.131439 0.078 Uiso 1 1 d G U . . .
N4 N 0.51801(7) 0.80864(19) 0.54960(11) 0.0349(4) Uani 1 1 d . . . . .
N2 N 0.57461(7) 1.08334(18) 0.79959(12) 0.0347(4) Uani 1 1 d . . . . .
N1 N 0.65861(7) 1.1594(2) 0.77214(13) 0.0384(4) Uani 1 1 d . . . . .
C6 C 0.46994(9) 0.7388(2) 0.56034(13) 0.0314(4) Uani 1 1 d . . . . .
N5 N 0.37499(9) 0.4296(2) 0.31732(14) 0.0487(5) Uani 1 1 d . . . . .
C7 C 0.43777(9) 0.6314(2) 0.47445(14) 0.0339(4) Uani 1 1 d . . . . .
C4 C 0.60799(8) 1.0740(2) 0.73623(14) 0.0330(4) Uani 1 1 d . . . . .
C5 C 0.58951(9) 0.9802(2) 0.64383(14) 0.0358(4) Uani 1 1 d . . . . .
H5 H 0.610517 0.977435 0.595649 0.043 Uiso 1 1 calc R U . . .
O3 O 0.24835(11) 0.4720(2) 0.02066(19) 0.0851(7) Uani 1 1 d G . . . .
H3B H 0.268166 0.398179 0.056770 0.128 Uiso 1 1 d G U . . .
H3A H 0.227840 0.428752 -0.034951 0.128 Uiso 1 1 d G U . . .
C3 C 0.60551(10) 1.1780(2) 0.87891(15) 0.0413(5) Uani 1 1 d . . . . .
H3 H 0.592934 1.205209 0.935293 0.050 Uiso 1 1 calc R U . . .
C8 C 0.45441(10) 0.6134(2) 0.38493(14) 0.0392(5) Uani 1 1 d . . . . .
H8 H 0.486533 0.668866 0.375712 0.047 Uiso 1 1 calc R U . . .
C11 C 0.39011(10) 0.5436(2) 0.48356(16) 0.0447(5) Uani 1 1 d . . . . .
H11 H 0.378251 0.549735 0.542885 0.054 Uiso 1 1 calc R U . . .
C9 C 0.42212(11) 0.5111(3) 0.30983(15) 0.0459(5) Uani 1 1 d . . . . .
H9 H 0.433966 0.498518 0.250860 0.055 Uiso 1 1 calc R U . . .
C2 C 0.65683(10) 1.2256(2) 0.86287(16) 0.0436(5) Uani 1 1 d . . . . .
H2 H 0.685546 1.290770 0.905215 0.052 Uiso 1 1 calc R U . . .
C10 C 0.36021(11) 0.4463(3) 0.40328(17) 0.0501(6) Uani 1 1 d . . . . .
H10 H 0.327845 0.389405 0.410285 0.060 Uiso 1 1 calc R U . . .
C1 C 0.70643(10) 1.1762(3) 0.7245(2) 0.0590(6) Uani 1 1 d . . . . .
H1A H 0.729417 1.081973 0.733692 0.089 Uiso 1 1 calc R U . . .
H1B H 0.732047 1.260913 0.756369 0.089 Uiso 1 1 calc R U . . .
H1C H 0.689312 1.196771 0.652232 0.089 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 2.0971(16) 2_656 ?
Zn1 N3 2.0971(16) . ?
Zn1 N2 2.1806(16) . ?
Zn1 N2 2.1807(16) 2_656 ?
Zn1 O1 2.1877(13) 2_656 ?
Zn1 O1 2.1877(13) . ?
O1 C6 1.278(2) . ?
N3 C5 1.276(3) . ?
N3 N4 1.373(2) . ?
O2 H2A 0.8501 . ?
O2 H2B 0.8500 . ?
N4 C6 1.321(3) . ?
N2 C4 1.328(3) . ?
N2 C3 1.371(2) . ?
N1 C4 1.354(2) . ?
N1 C2 1.370(3) . ?
N1 C1 1.458(3) . ?
C6 C7 1.502(2) . ?
N5 C10 1.323(3) . ?
N5 C9 1.336(3) . ?
C7 C11 1.383(3) . ?
C7 C8 1.394(3) . ?
C4 C5 1.446(3) . ?
C5 H5 0.9300 . ?
O3 H3B 0.8500 . ?
O3 H3A 0.8499 . ?
C3 C2 1.347(3) . ?
C3 H3 0.9300 . ?
C8 C9 1.387(3) . ?
C8 H8 0.9300 . ?
C11 C10 1.387(3) . ?
C11 H11 0.9300 . ?
C9 H9 0.9300 . ?
C2 H2 0.9300 . ?
C10 H10 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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
N3 Zn1 N3 171.09(8) 2_656 . ?
N3 Zn1 N2 109.19(6) 2_656 . ?
N3 Zn1 N2 76.76(6) . . ?
N3 Zn1 N2 76.76(6) 2_656 2_656 ?
N3 Zn1 N2 109.20(6) . 2_656 ?
N2 Zn1 N2 100.07(9) . 2_656 ?
N3 Zn1 O1 72.42(6) 2_656 2_656 ?
N3 Zn1 O1 101.52(6) . 2_656 ?
N2 Zn1 O1 89.26(6) . 2_656 ?
N2 Zn1 O1 149.17(6) 2_656 2_656 ?
N3 Zn1 O1 101.52(6) 2_656 . ?
N3 Zn1 O1 72.42(6) . . ?
N2 Zn1 O1 149.17(6) . . ?
N2 Zn1 O1 89.26(6) 2_656 . ?
O1 Zn1 O1 97.64(8) 2_656 . ?
C6 O1 Zn1 111.83(12) . . ?
C5 N3 N4 121.22(16) . . ?
C5 N3 Zn1 118.13(13) . . ?
N4 N3 Zn1 120.65(12) . . ?
H2A O2 H2B 104.5 . . ?
C6 N4 N3 108.53(15) . . ?
C4 N2 C3 105.80(17) . . ?
C4 N2 Zn1 109.44(12) . . ?
C3 N2 Zn1 143.94(14) . . ?
C4 N1 C2 106.85(17) . . ?
C4 N1 C1 126.75(18) . . ?
C2 N1 C1 126.39(19) . . ?
O1 C6 N4 126.47(17) . . ?
O1 C6 C7 117.55(17) . . ?
N4 C6 C7 115.97(16) . . ?
C10 N5 C9 116.82(18) . . ?
C11 C7 C8 117.50(18) . . ?
C11 C7 C6 119.70(17) . . ?
C8 C7 C6 122.79(19) . . ?
N2 C4 N1 110.77(17) . . ?
N2 C4 C5 121.12(17) . . ?
N1 C4 C5 128.10(18) . . ?
N3 C5 C4 114.20(17) . . ?
N3 C5 H5 122.9 . . ?
C4 C5 H5 122.9 . . ?
H3B O3 H3A 104.5 . . ?
C2 C3 N2 109.75(18) . . ?
C2 C3 H3 125.1 . . ?
N2 C3 H3 125.1 . . ?
C9 C8 C7 118.7(2) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C7 C11 C10 119.3(2) . . ?
C7 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
N5 C9 C8 123.8(2) . . ?
N5 C9 H9 118.1 . . ?
C8 C9 H9 118.1 . . ?
C3 C2 N1 106.82(18) . . ?
C3 C2 H2 126.6 . . ?
N1 C2 H2 126.6 . . ?
N5 C10 C11 123.9(2) . . ?
N5 C10 H10 118.1 . . ?
C11 C10 H10 118.1 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
C5 N3 N4 C6 178.68(18) . . . . ?
Zn1 N3 N4 C6 -2.21(19) . . . . ?
Zn1 O1 C6 N4 2.6(2) . . . . ?
Zn1 O1 C6 C7 -177.92(12) . . . . ?
N3 N4 C6 O1 -0.4(3) . . . . ?
N3 N4 C6 C7 -179.95(14) . . . . ?
O1 C6 C7 C11 -5.1(3) . . . . ?
N4 C6 C7 C11 174.50(18) . . . . ?
O1 C6 C7 C8 176.06(18) . . . . ?
N4 C6 C7 C8 -4.4(3) . . . . ?
C3 N2 C4 N1 -0.2(2) . . . . ?
Zn1 N2 C4 N1 -172.45(12) . . . . ?
C3 N2 C4 C5 178.87(17) . . . . ?
Zn1 N2 C4 C5 6.6(2) . . . . ?
C2 N1 C4 N2 0.0(2) . . . . ?
C1 N1 C4 N2 179.19(19) . . . . ?
C2 N1 C4 C5 -178.95(19) . . . . ?
C1 N1 C4 C5 0.2(3) . . . . ?
N4 N3 C5 C4 178.95(15) . . . . ?
Zn1 N3 C5 C4 -0.2(2) . . . . ?
N2 C4 C5 N3 -4.7(3) . . . . ?
N1 C4 C5 N3 174.20(18) . . . . ?
C4 N2 C3 C2 0.3(2) . . . . ?
Zn1 N2 C3 C2 167.80(17) . . . . ?
C11 C7 C8 C9 0.9(3) . . . . ?
C6 C7 C8 C9 179.80(18) . . . . ?
C8 C7 C11 C10 -1.9(3) . . . . ?
C6 C7 C11 C10 179.19(18) . . . . ?
C10 N5 C9 C8 -1.9(3) . . . . ?
C7 C8 C9 N5 1.0(3) . . . . ?
N2 C3 C2 N1 -0.3(2) . . . . ?
C4 N1 C2 C3 0.1(2) . . . . ?
C1 N1 C2 C3 -179.0(2) . . . . ?
C9 N5 C10 C11 0.8(3) . . . . ?
C7 C11 C10 N5 1.1(4) . . . . ?

_refine_diff_density_max         0.387
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.083



####################################################################### 
# 
# 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_SMSPZn_a
_database_code_depnum_ccdc_archive 'CCDC 2209946'
loop_
_audit_author_name
_audit_author_address
'Samit Pramanik'
;Jadavpur University
India
;
_audit_update_record             
;
2022-09-28 deposited with the CCDC.	2022-12-19 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         'C11 H12 Cl3 N5 O Zn, H2 O'
_chemical_formula_sum            'C11 H14 Cl3 N5 O2 Zn'
_chemical_formula_weight         420.01

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'
Cl Cl 0.1484 0.1585 '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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   9.473(4)
_cell_length_b                   13.927(6)
_cell_length_c                   13.293(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.063(5)
_cell_angle_gamma                90
_cell_volume                     1693.5(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296
_cell_measurement_reflns_used    4022
_cell_measurement_theta_min      2.158
_cell_measurement_theta_max      27.842

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    1.935
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.747
_exptl_absorpt_correction_T_max  0.840
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23619
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.158
_diffrn_reflns_theta_max         27.842
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3861
_reflns_number_gt                2754
_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       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'APEX2(Bruker,2007)and SAINT (Bruker,2007)'
_computing_data_reduction        'SAINT(Bruker,2007)and XPREP(Bruker,2007)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    
;    
ORTEP-3 for Windows (Farrugia, 1997), DIAMOND (Brandenburg,
1999) and Mercury (Macrae et al., 2006)
;
_computing_publication_material  'PLATON (Spek, 2009)'
_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)+(0.0339P)²+0.6250P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4022
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0804
_refine_ls_wR_factor_gt          0.0715
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_restrained_S_all      0.971
_refine_ls_shift/su_max          0.019
_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 0.41269(3) 0.99652(2) 0.68273(2) 0.03827(11) Uani 1 1 d . . . . .
Cl2 Cl 0.47090(8) 0.96233(5) 0.85697(5) 0.04675(18) Uani 1 1 d . . . . .
Cl3 Cl 0.51167(8) 1.13953(5) 0.65896(5) 0.04618(18) Uani 1 1 d . . . . .
Cl1 Cl 0.17676(9) 0.97151(6) 0.61151(7) 0.0653(2) Uani 1 1 d . . . . .
O1 O 0.9774(2) 0.70584(13) 0.62434(16) 0.0482(5) Uani 1 1 d . . . . .
N2 N 1.1432(2) 0.38954(14) 0.62571(15) 0.0355(5) Uani 1 1 d . . . . .
H2C H 1.176110 0.447259 0.627677 0.043 Uiso 1 1 calc R U . . .
N4 N 0.8117(2) 0.58701(14) 0.61256(17) 0.0390(5) Uani 1 1 d . . . . .
H4C H 0.722890 0.570028 0.607583 0.047 Uiso 1 1 calc R U . . .
N5 N 0.5367(2) 0.89679(14) 0.62818(15) 0.0357(5) Uani 1 1 d . . . . .
N3 N 0.9208(2) 0.52067(14) 0.61761(17) 0.0385(5) Uani 1 1 d . . . . .
N1 N 0.9968(2) 0.26910(15) 0.61758(16) 0.0394(5) Uani 1 1 d . . . . .
O2 O 0.2246(2) 0.58450(16) 0.62750(19) 0.0634(6) Uani 1 1 d G . . . .
H2A H 0.147418 0.613040 0.632578 0.095 Uiso 1 1 d G U . . .
H2B H 0.289929 0.602482 0.680962 0.095 Uiso 1 1 d G U . . .
C4 C 1.0044(3) 0.36541(17) 0.61921(18) 0.0326(6) Uani 1 1 d . . . . .
C7 C 0.7328(3) 0.75365(17) 0.61162(18) 0.0326(6) Uani 1 1 d . . . . .
C11 C 0.7713(3) 0.84950(18) 0.60989(19) 0.0375(6) Uani 1 1 d . . . . .
H11 H 0.863393 0.866939 0.603675 0.045 Uiso 1 1 calc R U . . .
C6 C 0.8518(3) 0.68070(18) 0.61586(19) 0.0339(6) Uani 1 1 d . . . . .
C3 C 1.2246(3) 0.30803(19) 0.62873(19) 0.0398(6) Uani 1 1 d . . . . .
H3 H 1.324267 0.305157 0.633858 0.048 Uiso 1 1 calc R U . . .
C9 C 0.4983(3) 0.80432(18) 0.6239(2) 0.0403(6) Uani 1 1 d . . . . .
H9 H 0.404195 0.788796 0.627376 0.048 Uiso 1 1 calc R U . . .
C8 C 0.5916(3) 0.73072(18) 0.6147(2) 0.0385(6) Uani 1 1 d . . . . .
H8 H 0.560454 0.667167 0.610624 0.046 Uiso 1 1 calc R U . . .
C2 C 1.1343(3) 0.23305(19) 0.6229(2) 0.0421(7) Uani 1 1 d . . . . .
H2 H 1.159590 0.168547 0.622600 0.051 Uiso 1 1 calc R U . . .
C5 C 0.8866(3) 0.43243(18) 0.6152(2) 0.0410(6) Uani 1 1 d . . . . .
H5 H 0.791728 0.412180 0.611023 0.049 Uiso 1 1 calc R U . . .
C10 C 0.6699(3) 0.91868(18) 0.6176(2) 0.0394(6) Uani 1 1 d . . . . .
H10 H 0.695202 0.983025 0.615377 0.047 Uiso 1 1 calc R U . . .
C1 C 0.8648(4) 0.2113(2) 0.6093(3) 0.0632(9) Uani 1 1 d . . . . .
H1A H 0.844579 0.207456 0.676356 0.095 Uiso 1 1 calc R U . . .
H1C H 0.879705 0.147936 0.585729 0.095 Uiso 1 1 calc R U . . .
H1B H 0.783608 0.240871 0.560558 0.095 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 N5 2.068(2) . ?
Zn1 Cl1 2.2166(12) . ?
Zn1 Cl3 2.2583(10) . ?
Zn1 Cl2 2.2873(12) . ?
O1 C6 1.217(3) . ?
N2 C4 1.338(3) . ?
N2 C3 1.367(3) . ?
N2 H2C 0.8600 . ?
N4 C6 1.356(3) . ?
N4 N3 1.375(3) . ?
N4 H4C 0.8600 . ?
N5 C9 1.335(3) . ?
N5 C10 1.341(3) . ?
N3 C5 1.269(3) . ?
N1 C4 1.343(3) . ?
N1 C2 1.380(3) . ?
N1 C1 1.467(4) . ?
O2 H2A 0.8500 . ?
O2 H2B 0.8500 . ?
C4 C5 1.445(3) . ?
C7 C11 1.386(3) . ?
C7 C8 1.386(4) . ?
C7 C6 1.508(3) . ?
C11 C10 1.383(3) . ?
C11 H11 0.9300 . ?
C3 C2 1.339(4) . ?
C3 H3 0.9300 . ?
C9 C8 1.380(3) . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?
C2 H2 0.9300 . ?
C5 H5 0.9300 . ?
C10 H10 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1C 0.9600 . ?
C1 H1B 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
N5 Zn1 Cl1 110.26(7) . . ?
N5 Zn1 Cl3 104.41(7) . . ?
Cl1 Zn1 Cl3 119.21(3) . . ?
N5 Zn1 Cl2 101.87(6) . . ?
Cl1 Zn1 Cl2 110.54(3) . . ?
Cl3 Zn1 Cl2 109.01(3) . . ?
C4 N2 C3 109.3(2) . . ?
C4 N2 H2C 125.4 . . ?
C3 N2 H2C 125.4 . . ?
C6 N4 N3 116.4(2) . . ?
C6 N4 H4C 121.8 . . ?
N3 N4 H4C 121.8 . . ?
C9 N5 C10 117.9(2) . . ?
C9 N5 Zn1 119.28(18) . . ?
C10 N5 Zn1 121.33(17) . . ?
C5 N3 N4 117.8(2) . . ?
C4 N1 C2 108.5(2) . . ?
C4 N1 C1 126.1(2) . . ?
C2 N1 C1 125.4(2) . . ?
H2A O2 H2B 104.5 . . ?
N2 C4 N1 107.4(2) . . ?
N2 C4 C5 125.2(2) . . ?
N1 C4 C5 127.4(2) . . ?
C11 C7 C8 118.9(2) . . ?
C11 C7 C6 116.9(2) . . ?
C8 C7 C6 124.2(2) . . ?
C10 C11 C7 118.6(2) . . ?
C10 C11 H11 120.7 . . ?
C7 C11 H11 120.7 . . ?
O1 C6 N4 122.6(2) . . ?
O1 C6 C7 120.9(2) . . ?
N4 C6 C7 116.5(2) . . ?
C2 C3 N2 107.4(2) . . ?
C2 C3 H3 126.3 . . ?
N2 C3 H3 126.3 . . ?
N5 C9 C8 123.1(3) . . ?
N5 C9 H9 118.4 . . ?
C8 C9 H9 118.4 . . ?
C9 C8 C7 118.5(2) . . ?
C9 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
C3 C2 N1 107.4(2) . . ?
C3 C2 H2 126.3 . . ?
N1 C2 H2 126.3 . . ?
N3 C5 C4 115.8(2) . . ?
N3 C5 H5 122.1 . . ?
C4 C5 H5 122.1 . . ?
N5 C10 C11 122.7(2) . . ?
N5 C10 H10 118.7 . . ?
C11 C10 H10 118.7 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1C C1 H1B 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 N4 N3 C5 179.7(2) . . . . ?
C3 N2 C4 N1 -0.3(3) . . . . ?
C3 N2 C4 C5 179.5(2) . . . . ?
C2 N1 C4 N2 -0.2(3) . . . . ?
C1 N1 C4 N2 -179.0(2) . . . . ?
C2 N1 C4 C5 -180.0(2) . . . . ?
C1 N1 C4 C5 1.2(4) . . . . ?
C8 C7 C11 C10 3.8(4) . . . . ?
C6 C7 C11 C10 -173.0(2) . . . . ?
N3 N4 C6 O1 -1.0(4) . . . . ?
N3 N4 C6 C7 -179.3(2) . . . . ?
C11 C7 C6 O1 4.7(3) . . . . ?
C8 C7 C6 O1 -171.9(2) . . . . ?
C11 C7 C6 N4 -177.0(2) . . . . ?
C8 C7 C6 N4 6.4(4) . . . . ?
C4 N2 C3 C2 0.6(3) . . . . ?
C10 N5 C9 C8 3.5(4) . . . . ?
Zn1 N5 C9 C8 -162.9(2) . . . . ?
N5 C9 C8 C7 1.2(4) . . . . ?
C11 C7 C8 C9 -4.9(4) . . . . ?
C6 C7 C8 C9 171.7(2) . . . . ?
N2 C3 C2 N1 -0.7(3) . . . . ?
C4 N1 C2 C3 0.5(3) . . . . ?
C1 N1 C2 C3 179.4(3) . . . . ?
N4 N3 C5 C4 179.2(2) . . . . ?
N2 C4 C5 N3 0.3(4) . . . . ?
N1 C4 C5 N3 -179.9(2) . . . . ?
C9 N5 C10 C11 -4.6(4) . . . . ?
Zn1 N5 C10 C11 161.5(2) . . . . ?
C7 C11 C10 N5 1.0(4) . . . . ?

_refine_diff_density_max         0.273
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.062



