# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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. 
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#######################################################################

data_Complex-7
_database_code_depnum_ccdc_archive 'CCDC 1555235'
_audit_update_record             
;
2017-06-09 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT084_Complex-7           
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.36 Report 
RESPONSE: The crystals of this complex were small sized with poor X-ray 
 diffraction and repeated recrystallization under different environments
 did not converged to better quality crystals. This alert is due to the 
 low quality of the diffraction data. The reported structure is the best
 possible solution so far achieved after refinement with some constraints. 	
;
_vrf_PLAT201_Complex-7           
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          2 Report 
RESPONSE: Among 5 disordered atoms on one morpholine ring, the displacement
 parameters of two carbon atoms (C19 and C21) became non-positive definit
 during anisotropic refinement. Therefore these were refined isotropically
 for disorder modelling.  	
;
_vrf_PLAT306_Complex-7           
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) .......         O7 Check 
RESPONSE: The hydrogen atoms associated with the solvate water molecules 
 could not be located in the difference density map. 	
;
_vrf_PLAT601_Complex-7           
;
PROBLEM: Structure Contains Solvent Accessible VOIDS of .        171 Ang3  
RESPONSE:  This may be associated to the large cavity formed by complex and
 solvate water molecules. In order to highlight the contribution of solvent 
 molecules in crystallization, the PLATON/SQUEEZE option was not invoked.     	
;

_audit_creation_date             2017-08-06
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            none
_chemical_melting_point          'not measured'
_chemical_formula_moiety         'C22 H32 N16 Ni O4, 0.269(O2), 2(Cl), 2.462(O)'
_chemical_formula_sum            'C22 H32 Cl2 N16 Ni O7'
_chemical_formula_weight         762.23

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'
Ni Ni 0.3393 1.1124 '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      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                   12.261(3)
_cell_length_b                   12.784(4)
_cell_length_c                   13.598(4)
_cell_angle_alpha                74.133(8)
_cell_angle_beta                 70.006(8)
_cell_angle_gamma                64.470(7)
_cell_volume                     1787.3(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9953
_cell_measurement_theta_min      3.053
_cell_measurement_theta_max      26.928

_exptl_crystal_description       Needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_F_000             788
_exptl_transmission_factor_min   0.968
_exptl_transmission_factor_max   0.977
_exptl_crystal_size_max          0.288
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.076
_exptl_absorpt_coefficient_mu    0.754
_shelx_estimated_absorpt_T_min   0.812
_shelx_estimated_absorpt_T_max   0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.868
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_process_details   
;
 SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1185  before and 0.0752 after correction. The Ratio of minimum to maximum transmission is  0.9073. The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   
;
 The crystal was mounted using Paratone-N oil (cryoprotectant)
 on the tip of MiTeGen MicroLoops LD?. It was placed on magnetic 
 head of goniometer directly into the cold gas stream of a 
 liquid-nitrogen based cryostat.
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focused sealed tube'
_diffrn_measurement_device_type  
;
 Bruker D8 Quest with Photon 100 CMOS Detector
;
_diffrn_measurement_method       
;
 φ and ω scans with 0.5 deg/frame and 20 seconds of
 exposure time. Detector was at 50mm from crystal.
;
_diffrn_detector                 'Photon 100 CMOS detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_radiation_monochromator  'Multi-layer X-ray mirror'
_diffrn_radiation_probe          x-ray
_diffrn_reflns_number            68001
_diffrn_reflns_av_unetI/netI     0.1003
_diffrn_reflns_av_R_equivalents  0.1408
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.796
_diffrn_reflns_theta_max         27.310
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7929
_reflns_number_gt                4657
_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       'Apex3 (Bruker AXS Inc., 2016)'
_computing_cell_refinement       'Apex3 (Bruker AXS Inc., 2016)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
 ORTEp-3 (Farrugia, 2012) and Olex2 (Dolomanov et al., 2009)
;
_computing_publication_material  'WinGX2014.1 (Farrugia, 2012)'
_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)+(0.1734P)²+12.0684P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     mixed
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7929
_refine_ls_number_parameters     462
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1972
_refine_ls_R_factor_gt           0.1218
_refine_ls_wR_factor_ref         0.3581
_refine_ls_wR_factor_gt          0.3076
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_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
Cl1A Cl 0.35(6) -0.14(2) 0.72(3) 0.28(2) Uani 0.538(7) 1 d . . P A 1
O5A O 0.372(2) -0.0764(11) 0.5007(12) 0.108(6) Uani 0.538(7) 1 d . . P A 1
O6A O 0.4843(17) -0.0070(15) 0.9725(14) 0.068(3) Uiso 0.538(7) 1 d . . P A 1
C19A C 0.9358(14) 0.3345(15) 0.4244(12) 0.031(3) Uiso 0.538(7) 1 d . . P A 1
H19A H 0.9210 0.2851 0.3894 0.037 Uiso 0.538(7) 1 calc R U P A 1
H19B H 0.8888 0.4172 0.3989 0.037 Uiso 0.538(7) 1 calc R U P A 1
C20A C 1.0587(17) 0.317(2) 0.3895(13) 0.047(4) Uani 0.538(7) 1 d . . P A 1
H20A H 1.0685 0.3754 0.3257 0.056 Uiso 0.538(7) 1 calc R U P A 1
H20B H 1.1027 0.2389 0.3658 0.056 Uiso 0.538(7) 1 calc R U P A 1
C21A C 0.9689(14) 0.2667(16) 0.6030(12) 0.028(3) Uiso 0.538(7) 1 d . . P A 1
H21A H 0.9235 0.2622 0.6789 0.033 Uiso 0.538(7) 1 calc R U P A 1
H21B H 1.0300 0.1873 0.5890 0.033 Uiso 0.538(7) 1 calc R U P A 1
C22A C 1.0323(18) 0.3478(19) 0.5756(14) 0.048(4) Uani 0.538(7) 1 d . . P A 1
H22A H 1.0807 0.3321 0.6267 0.058 Uiso 0.538(7) 1 calc R U P A 1
H22B H 0.9720 0.4301 0.5731 0.058 Uiso 0.538(7) 1 calc R U P A 1
O4A O 1.1264(14) 0.3206(16) 0.4561(16) 0.038(4) Uani 0.538(7) 1 d . . P A 1
Cl1B Cl 0.34(7) -0.14(3) 0.72(3) 0.28(2) Uani 0.462(7) 1 d . . P A 2
O5B O 0.612(2) -0.1372(13) 0.5344(14) 0.108(6) Uani 0.462(7) 1 d . . P A 2
O6B O 0.5395(19) -0.0199(17) 0.9344(16) 0.068(3) Uiso 0.462(7) 1 d . . P A 2
C19B C 0.9190(17) 0.3856(18) 0.4306(14) 0.031(3) Uiso 0.462(7) 1 d . . P A 2
H19C H 0.9337 0.3412 0.3749 0.037 Uiso 0.462(7) 1 calc R U P A 2
H19D H 0.8442 0.4577 0.4245 0.037 Uiso 0.462(7) 1 calc R U P A 2
C20B C 0.996(2) 0.413(2) 0.4083(16) 0.047(4) Uani 0.462(7) 1 d . . P A 2
H20C H 0.9594 0.4997 0.4045 0.056 Uiso 0.462(7) 1 calc R U P A 2
H20D H 1.0417 0.3969 0.3351 0.056 Uiso 0.462(7) 1 calc R U P A 2
C21B C 0.9472(16) 0.3176(19) 0.6113(14) 0.027(4) Uiso 0.462(7) 1 d . . P A 2
H21C H 0.9225 0.2755 0.6828 0.032 Uiso 0.462(7) 1 calc R U P A 2
H21D H 0.9272 0.3998 0.6170 0.032 Uiso 0.462(7) 1 calc R U P A 2
C22B C 1.089(2) 0.256(2) 0.5586(17) 0.048(4) Uani 0.462(7) 1 d . . P A 2
H22C H 1.1090 0.1845 0.5306 0.058 Uiso 0.462(7) 1 calc R U P A 2
H22D H 1.1441 0.2400 0.6047 0.058 Uiso 0.462(7) 1 calc R U P A 2
O4B O 1.0874(17) 0.3698(19) 0.467(2) 0.038(4) Uani 0.462(7) 1 d . . P A 2
Ni1 Ni 0.36485(8) 0.29947(9) 0.72063(8) 0.0278(3) Uani 1 1 d . . . . .
O1 O -0.3353(5) 0.1717(6) 0.9873(5) 0.0433(15) Uani 1 1 d . . . . .
O2 O 0.2872(5) 0.4696(5) 0.7492(4) 0.0272(12) Uani 1 1 d . . . . .
O3 O 0.3200(5) 0.3508(5) 0.5794(4) 0.0344(13) Uani 1 1 d . . . . .
N1 N -0.1160(6) 0.2164(6) 0.9042(7) 0.045(2) Uani 1 1 d . . . . .
N2 N 0.0954(6) 0.1514(6) 0.8323(5) 0.0305(15) Uani 1 1 d . . . . .
N3 N -0.0200(6) 0.3475(6) 0.8714(6) 0.0343(16) Uani 1 1 d . . . . .
N4 N 0.1987(5) 0.2830(5) 0.7960(5) 0.0215(12) Uani 1 1 d . . . . .
N5 N -0.0277(6) 0.5553(6) 0.8811(5) 0.0300(15) Uani 1 1 d . . . . .
N6 N 0.0834(6) 0.4721(5) 0.8371(5) 0.0258(13) Uani 1 1 d . . . . .
N7 N 0.3032(6) 0.0968(6) 0.7539(5) 0.0295(15) Uani 1 1 d . . . . .
N8 N 0.4113(6) 0.1255(6) 0.7060(7) 0.0417(18) Uani 1 1 d . . . . .
H8A H 0.4392 0.1168 0.6364 0.050 Uiso 1 1 calc R U . . .
H8B H 0.4732 0.0768 0.7382 0.050 Uiso 1 1 calc R U . . .
N9 N 0.4418(6) 0.2459(6) 0.8501(5) 0.0308(15) Uani 1 1 d . . . . .
H9A H 0.3968 0.2980 0.8970 0.037 Uiso 1 1 calc R U . . .
H9B H 0.4399 0.1744 0.8838 0.037 Uiso 1 1 calc R U . . .
N10 N 0.5665(6) 0.2401(7) 0.8123(6) 0.0344(16) Uani 1 1 d . . . . .
N11 N 0.5340(6) 0.3064(6) 0.6472(5) 0.0253(13) Uani 1 1 d . . . . .
N12 N 0.7278(6) 0.2722(6) 0.6786(5) 0.0322(15) Uani 1 1 d . . . . .
N13 N 0.6972(6) 0.3415(6) 0.5031(5) 0.0290(15) Uani 1 1 d . . . . .
N14 N 0.8807(6) 0.3124(7) 0.5364(6) 0.0393(18) Uani 1 1 d . . . . .
N15 N 0.5090(5) 0.3744(6) 0.4765(5) 0.0248(13) Uani 1 1 d . . . . .
N16 N 0.5578(6) 0.4014(6) 0.3696(5) 0.0275(14) Uani 1 1 d . . . . .
C1 C -0.2172(8) 0.0760(9) 0.9815(9) 0.050(3) Uani 1 1 d . . . . .
H1A H -0.2242 0.0056 0.9712 0.061 Uiso 1 1 calc R U . . .
H1B H -0.1940 0.0580 1.0488 0.061 Uiso 1 1 calc R U . . .
C2 C -0.3301(8) 0.2724(9) 1.0053(9) 0.049(2) Uani 1 1 d . . . . .
H2A H -0.3083 0.2553 1.0733 0.059 Uiso 1 1 calc R U . . .
H2B H -0.4137 0.3361 1.0114 0.059 Uiso 1 1 calc R U . . .
C3 C -0.1190(9) 0.1044(8) 0.8934(9) 0.049(2) Uani 1 1 d . . . . .
H3A H -0.1363 0.1128 0.8251 0.059 Uiso 1 1 calc R U . . .
H3B H -0.0367 0.0403 0.8945 0.059 Uiso 1 1 calc R U . . .
C4 C -0.2394(8) 0.3116(8) 0.9216(8) 0.046(2) Uani 1 1 d . . . . .
H4A H -0.2335 0.3781 0.9406 0.055 Uiso 1 1 calc R U . . .
H4B H -0.2671 0.3393 0.8555 0.055 Uiso 1 1 calc R U . . .
C5 C -0.0111(7) 0.2378(7) 0.8683(7) 0.0341(19) Uani 1 1 d . . . . .
C6 C 0.1970(6) 0.1777(6) 0.7959(6) 0.0245(16) Uani 1 1 d . . . . .
C7 C 0.0879(7) 0.3609(6) 0.8355(6) 0.0236(15) Uani 1 1 d . . . . .
C8 C -0.1136(9) 0.7616(8) 0.9072(8) 0.044(2) Uani 1 1 d . . . . .
H8C H -0.1462 0.8127 0.8471 0.067 Uiso 1 1 calc R U . . .
H8D H -0.0830 0.8028 0.9363 0.067 Uiso 1 1 calc R U . . .
H8E H -0.1804 0.7406 0.9620 0.067 Uiso 1 1 calc R U . . .
C9 C -0.0091(8) 0.6534(7) 0.8712(6) 0.0336(18) Uani 1 1 d . . . . .
C10 C 0.1142(8) 0.6367(7) 0.8225(6) 0.0332(18) Uani 1 1 d . . . . .
H10A H 0.1513 0.6928 0.8082 0.040 Uiso 1 1 calc R U . . .
C11 C 0.1756(7) 0.5226(7) 0.7978(6) 0.0268(16) Uani 1 1 d . . . . .
C12 C 0.3891(7) 0.3735(7) 0.4919(7) 0.0293(17) Uani 1 1 d . . . . .
C13 C 0.3686(7) 0.4050(8) 0.3905(6) 0.0319(18) Uani 1 1 d . . . . .
H13 H 0.2960 0.4125 0.3741 0.038 Uiso 1 1 calc R U . . .
C14 C 0.4721(6) 0.4232(7) 0.3190(6) 0.0259(16) Uani 1 1 d . . . . .
C15 C 0.4987(7) 0.4590(8) 0.2027(6) 0.0341(19) Uani 1 1 d . . . . .
H15A H 0.4851 0.5426 0.1861 0.051 Uiso 1 1 calc R U . . .
H15B H 0.4428 0.4449 0.1752 0.051 Uiso 1 1 calc R U . . .
H15C H 0.5858 0.4132 0.1699 0.051 Uiso 1 1 calc R U . . .
C16 C 0.5857(7) 0.3372(7) 0.5449(6) 0.0267(16) Uani 1 1 d . . . . .
C17 C 0.6126(7) 0.2726(7) 0.7087(7) 0.0310(18) Uani 1 1 d . . . . .
C18 C 0.7661(7) 0.3081(7) 0.5739(6) 0.0309(18) Uani 1 1 d . . . . .
Cl2 Cl -0.3090(2) 0.5947(2) 0.9630(2) 0.0513(7) Uani 1 1 d . . . . .
O7 O -0.4137(14) 0.7935(12) 0.7964(12) 0.142(5) Uani 1 1 d . . . . .
H7 H 0.300(7) 0.023(8) 0.750(7) 0.03(2) Uiso 1 1 d . . . . .
H10 H 0.605(8) 0.206(8) 0.864(7) 0.03(2) Uiso 1 1 d . . . . .
H16 H 0.615(8) 0.424(7) 0.359(6) 0.02(2) Uiso 1 1 d . . . . .
H5 H -0.101(8) 0.540(7) 0.907(7) 0.03(2) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O6A O6A 1.03(3) 2_657 ?
C19A C20A 1.35(2) . ?
C19A N14 1.443(17) . ?
C19A H19A 0.9900 . ?
C19A H19B 0.9900 . ?
C20A O4A 1.44(3) . ?
C20A H20A 0.9900 . ?
C20A H20B 0.9900 . ?
C21A C22A 1.45(2) . ?
C21A N14 1.472(16) . ?
C21A H21A 0.9900 . ?
C21A H21B 0.9900 . ?
C22A O4A 1.67(3) . ?
C22A H22A 0.9900 . ?
C22A H22B 0.9900 . ?
O6B O6B 1.81(4) 2_657 ?
C19B C20B 1.07(2) . ?
C19B N14 1.532(19) . ?
C19B H19C 0.9900 . ?
C19B H19D 0.9900 . ?
C20B O4B 1.43(3) . ?
C20B H20C 0.9900 . ?
C20B H20D 0.9900 . ?
C21B N14 1.535(18) . ?
C21B C22B 1.56(3) . ?
C21B H21C 0.9900 . ?
C21B H21D 0.9900 . ?
C22B O4B 1.63(3) . ?
C22B H22C 0.9900 . ?
C22B H22D 0.9900 . ?
Ni1 N11 2.000(6) . ?
Ni1 N4 2.017(6) . ?
Ni1 O3 2.035(6) . ?
Ni1 O2 2.052(5) . ?
Ni1 N9 2.093(7) . ?
Ni1 N8 2.094(7) . ?
O1 C2 1.406(11) . ?
O1 C1 1.430(11) . ?
O2 C11 1.263(9) . ?
O3 C12 1.246(9) . ?
N1 C5 1.331(10) . ?
N1 C4 1.467(11) . ?
N1 C3 1.495(11) . ?
N2 C6 1.326(9) . ?
N2 C5 1.334(10) . ?
N3 C7 1.313(9) . ?
N3 C5 1.371(10) . ?
N4 C7 1.324(9) . ?
N4 C6 1.356(9) . ?
N5 C9 1.333(11) . ?
N5 N6 1.373(9) . ?
N5 H5 0.94(9) . ?
N6 C7 1.405(10) . ?
N6 C11 1.417(9) . ?
N7 C6 1.322(10) . ?
N7 N8 1.419(9) . ?
N7 H7 0.98(9) . ?
N8 H8A 0.9100 . ?
N8 H8B 0.9100 . ?
N9 N10 1.412(9) . ?
N9 H9A 0.9100 . ?
N9 H9B 0.9100 . ?
N10 C17 1.347(11) . ?
N10 H10 0.89(9) . ?
N11 C16 1.343(10) . ?
N11 C17 1.345(10) . ?
N12 C17 1.328(10) . ?
N12 C18 1.352(10) . ?
N13 C16 1.308(9) . ?
N13 C18 1.358(10) . ?
N14 C18 1.340(10) . ?
N15 N16 1.378(9) . ?
N15 C16 1.395(10) . ?
N15 C12 1.418(9) . ?
N16 C14 1.339(10) . ?
N16 H16 0.83(9) . ?
C1 C3 1.473(13) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C4 1.444(14) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C8 C9 1.485(12) . ?
C8 H8C 0.9800 . ?
C8 H8D 0.9800 . ?
C8 H8E 0.9800 . ?
C9 C10 1.372(12) . ?
C10 C11 1.399(11) . ?
C10 H10A 0.9500 . ?
C12 C13 1.404(12) . ?
C13 C14 1.376(11) . ?
C13 H13 0.9500 . ?
C14 C15 1.482(11) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
C20A C19A N14 119.4(13) . . ?
C20A C19A H19A 107.5 . . ?
N14 C19A H19A 107.5 . . ?
C20A C19A H19B 107.5 . . ?
N14 C19A H19B 107.5 . . ?
H19A C19A H19B 107.0 . . ?
C19A C20A O4A 121.9(16) . . ?
C19A C20A H20A 106.8 . . ?
O4A C20A H20A 106.8 . . ?
C19A C20A H20B 106.8 . . ?
O4A C20A H20B 106.8 . . ?
H20A C20A H20B 106.7 . . ?
C22A C21A N14 106.4(13) . . ?
C22A C21A H21A 110.4 . . ?
N14 C21A H21A 110.4 . . ?
C22A C21A H21B 110.4 . . ?
N14 C21A H21B 110.4 . . ?
H21A C21A H21B 108.6 . . ?
C21A C22A O4A 102.8(16) . . ?
C21A C22A H22A 111.2 . . ?
O4A C22A H22A 111.2 . . ?
C21A C22A H22B 111.2 . . ?
O4A C22A H22B 111.2 . . ?
H22A C22A H22B 109.1 . . ?
C20A O4A C22A 110.5(13) . . ?
C20B C19B N14 124.9(19) . . ?
C20B C19B H19C 106.1 . . ?
N14 C19B H19C 106.1 . . ?
C20B C19B H19D 106.1 . . ?
N14 C19B H19D 106.1 . . ?
H19C C19B H19D 106.3 . . ?
C19B C20B O4B 123(2) . . ?
C19B C20B H20C 106.6 . . ?
O4B C20B H20C 106.6 . . ?
C19B C20B H20D 106.6 . . ?
O4B C20B H20D 106.6 . . ?
H20C C20B H20D 106.6 . . ?
N14 C21B C22B 104.3(14) . . ?
N14 C21B H21C 110.9 . . ?
C22B C21B H21C 110.9 . . ?
N14 C21B H21D 110.9 . . ?
C22B C21B H21D 110.9 . . ?
H21C C21B H21D 108.9 . . ?
C21B C22B O4B 91.1(16) . . ?
C21B C22B H22C 113.4 . . ?
O4B C22B H22C 113.4 . . ?
C21B C22B H22D 113.4 . . ?
O4B C22B H22D 113.4 . . ?
H22C C22B H22D 110.7 . . ?
C20B O4B C22B 118.1(19) . . ?
N11 Ni1 N4 176.9(3) . . ?
N11 Ni1 O3 90.0(2) . . ?
N4 Ni1 O3 91.0(2) . . ?
N11 Ni1 O2 93.4(2) . . ?
N4 Ni1 O2 89.4(2) . . ?
O3 Ni1 O2 91.4(2) . . ?
N11 Ni1 N9 80.1(2) . . ?
N4 Ni1 N9 98.8(2) . . ?
O3 Ni1 N9 170.1(2) . . ?
O2 Ni1 N9 90.2(2) . . ?
N11 Ni1 N8 97.1(3) . . ?
N4 Ni1 N8 80.0(2) . . ?
O3 Ni1 N8 88.7(3) . . ?
O2 Ni1 N8 169.5(2) . . ?
N9 Ni1 N8 91.6(3) . . ?
C2 O1 C1 111.1(7) . . ?
C11 O2 Ni1 126.5(5) . . ?
C12 O3 Ni1 125.8(5) . . ?
C5 N1 C4 121.6(7) . . ?
C5 N1 C3 121.6(7) . . ?
C4 N1 C3 113.6(7) . . ?
C6 N2 C5 115.7(7) . . ?
C7 N3 C5 113.5(6) . . ?
C7 N4 C6 114.2(6) . . ?
C7 N4 Ni1 131.1(5) . . ?
C6 N4 Ni1 114.3(5) . . ?
C9 N5 N6 108.7(6) . . ?
C9 N5 H5 131(5) . . ?
N6 N5 H5 120(5) . . ?
N5 N6 C7 119.7(6) . . ?
N5 N6 C11 108.1(6) . . ?
C7 N6 C11 132.1(6) . . ?
C6 N7 N8 119.1(6) . . ?
C6 N7 H7 117(5) . . ?
N8 N7 H7 123(5) . . ?
N7 N8 Ni1 108.7(5) . . ?
N7 N8 H8A 109.9 . . ?
Ni1 N8 H8A 109.9 . . ?
N7 N8 H8B 109.9 . . ?
Ni1 N8 H8B 109.9 . . ?
H8A N8 H8B 108.3 . . ?
N10 N9 Ni1 108.2(5) . . ?
N10 N9 H9A 110.1 . . ?
Ni1 N9 H9A 110.1 . . ?
N10 N9 H9B 110.1 . . ?
Ni1 N9 H9B 110.1 . . ?
H9A N9 H9B 108.4 . . ?
C17 N10 N9 119.9(7) . . ?
C17 N10 H10 130(6) . . ?
N9 N10 H10 110(6) . . ?
C16 N11 C17 112.8(6) . . ?
C16 N11 Ni1 131.2(5) . . ?
C17 N11 Ni1 115.9(5) . . ?
C17 N12 C18 113.6(7) . . ?
C16 N13 C18 113.9(7) . . ?
C18 N14 C19A 121.7(8) . . ?
C18 N14 C21A 121.8(9) . . ?
C19A N14 C21A 114.9(10) . . ?
C18 N14 C19B 122.3(9) . . ?
C18 N14 C21B 120.5(9) . . ?
C19B N14 C21B 106.8(11) . . ?
N16 N15 C16 119.2(6) . . ?
N16 N15 C12 108.2(6) . . ?
C16 N15 C12 131.7(7) . . ?
C14 N16 N15 108.6(6) . . ?
C14 N16 H16 135(6) . . ?
N15 N16 H16 111(6) . . ?
O1 C1 C3 111.0(8) . . ?
O1 C1 H1A 109.4 . . ?
C3 C1 H1A 109.4 . . ?
O1 C1 H1B 109.4 . . ?
C3 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
O1 C2 C4 112.2(8) . . ?
O1 C2 H2A 109.2 . . ?
C4 C2 H2A 109.2 . . ?
O1 C2 H2B 109.2 . . ?
C4 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C1 C3 N1 109.3(8) . . ?
C1 C3 H3A 109.8 . . ?
N1 C3 H3A 109.8 . . ?
C1 C3 H3B 109.8 . . ?
N1 C3 H3B 109.8 . . ?
H3A C3 H3B 108.3 . . ?
C2 C4 N1 110.9(8) . . ?
C2 C4 H4A 109.5 . . ?
N1 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
N1 C5 N2 118.1(7) . . ?
N1 C5 N3 117.4(7) . . ?
N2 C5 N3 124.5(7) . . ?
N7 C6 N2 117.6(7) . . ?
N7 C6 N4 117.8(6) . . ?
N2 C6 N4 124.6(7) . . ?
N3 C7 N4 127.5(7) . . ?
N3 C7 N6 115.6(6) . . ?
N4 C7 N6 116.9(6) . . ?
C9 C8 H8C 109.5 . . ?
C9 C8 H8D 109.5 . . ?
H8C C8 H8D 109.5 . . ?
C9 C8 H8E 109.5 . . ?
H8C C8 H8E 109.5 . . ?
H8D C8 H8E 109.5 . . ?
N5 C9 C10 109.8(7) . . ?
N5 C9 C8 121.5(8) . . ?
C10 C9 C8 128.6(8) . . ?
C9 C10 C11 108.0(7) . . ?
C9 C10 H10A 126.0 . . ?
C11 C10 H10A 126.0 . . ?
O2 C11 C10 131.0(7) . . ?
O2 C11 N6 123.6(7) . . ?
C10 C11 N6 105.3(6) . . ?
O3 C12 C13 130.0(7) . . ?
O3 C12 N15 124.7(7) . . ?
C13 C12 N15 105.3(6) . . ?
C14 C13 C12 108.1(7) . . ?
C14 C13 H13 125.9 . . ?
C12 C13 H13 125.9 . . ?
N16 C14 C13 109.6(7) . . ?
N16 C14 C15 119.9(7) . . ?
C13 C14 C15 130.5(7) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N13 C16 N11 127.5(7) . . ?
N13 C16 N15 116.4(7) . . ?
N11 C16 N15 116.0(6) . . ?
N12 C17 N11 126.8(8) . . ?
N12 C17 N10 117.3(7) . . ?
N11 C17 N10 115.8(7) . . ?
N14 C18 N12 117.9(7) . . ?
N14 C18 N13 116.9(7) . . ?
N12 C18 N13 125.2(7) . . ?

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
N8 H8A O5A 0.91 2.37 3.125(16) 139.8 2_656
N8 H8A O5B 0.91 2.52 3.33(2) 148.4 2_656
N9 H9A Cl2 0.91 2.33 3.225(7) 168.6 2_567
N9 H9B O6A 0.91 2.23 3.113(19) 164.5 .
N9 H9B O6A 0.91 2.55 3.324(19) 143.2 2_657
N9 H9B O6B 0.91 2.27 3.10(2) 150.8 .
N7 H7 Cl1A 0.98(9) 2.1(4) 3.0(4) 163(19) .
N7 H7 Cl1B 0.98(9) 2.1(5) 3.0(5) 165(21) .
N10 H10 O1 0.89(9) 1.93(10) 2.792(9) 165(8) 1_655
N16 H16 O2 0.83(9) 2.13(9) 2.844(8) 144(8) 2_666
N5 H5 Cl2 0.94(9) 2.23(9) 3.094(7) 152(7) .

_refine_diff_density_max         2.176
_refine_diff_density_min         -1.198
_refine_diff_density_rms         0.202

####################################################################### 
# 
# 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_Complex-6
_database_code_depnum_ccdc_archive 'CCDC 1555236'
_audit_update_record             
;
2017-06-09 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT420_Complex-6           
;
PROBLEM: D-H Without Acceptor       O7     --  H7A    ...     Please Check
RESPONSE: This is due to the absence of clearly	identified peripheral H-bond 
acceptors to one of the solvate water molecule present in the structure.	
;

_audit_creation_date             2017-08-06
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            none
_chemical_melting_point          'not measured'
_chemical_formula_moiety         
'C11 H17 Cl Cu N8 O3, C11 H16 Cl2 Cu N8 O2, 3(H2 O), 0.5(O2)'
_chemical_formula_sum            'C22 H39 Cl3 Cu2 N16 O9'
_chemical_formula_weight         905.14

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'
Cu Cu 0.3201 1.2651 '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'

_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                   11.3979(6)
_cell_length_b                   12.0551(7)
_cell_length_c                   13.6836(7)
_cell_angle_alpha                97.586(2)
_cell_angle_beta                 103.997(2)
_cell_angle_gamma                106.156(2)
_cell_volume                     1711.75(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9886
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      27.82

_exptl_crystal_description       Needle
_exptl_crystal_colour            Blue
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   0.956
_exptl_transmission_factor_max   0.972
_exptl_crystal_size_max          0.226
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.045
_exptl_absorpt_coefficient_mu    1.551
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.876
_exptl_absorpt_correction_T_max  0.933
_exptl_absorpt_process_details   
;
 SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0675 before and    0.0632 after correction. The Ratio of minimum to maximum transmission is 0.9303. The λ/2    correction factor is 0.00150.
;
_exptl_absorpt_special_details   
;
 The crystal was mounted using Paratone-N oil (cryoprotectant)
 on the tip of MiTeGen MicroLoops LD?. It was placed on magnetic 
 head of goniometer directly into the cold gas stream of a 
 liquid-nitrogen based cryostat.
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focused sealed tube'
_diffrn_measurement_device_type  
;
 Bruker D8 Quest with Photon 100 CMOS Detector
;
_diffrn_measurement_method       
;
 φ and ω scans with 0.5 deg/frame and 20 seconds of
 exposure time. Detector was at 45mm from crystal.
;
_diffrn_detector                 'Photon 100 CMOS detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_radiation_monochromator  'Multi-layer X-ray mirror'
_diffrn_radiation_probe          x-ray
_diffrn_reflns_number            86344
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.959
_diffrn_reflns_theta_max         27.185
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7595
_reflns_number_gt                6122
_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       'Apex3 (Bruker AXS Inc., 2016)'
_computing_cell_refinement       'Apex3 (Bruker AXS Inc., 2016)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
 ORTEp-3 (Farrugia, 2012) and Olex2 (Dolomanov et al., 2009)
;
_computing_publication_material  'WinGX2014.1 (Farrugia, 2012)'
_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)+(0.0320P)²+4.0982P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     mixed
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7595
_refine_ls_number_parameters     535
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0886
_refine_ls_wR_factor_gt          0.0815
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
O8A O -0.1048(13) 0.1486(12) 0.9637(11) 0.0220(13) Uani 0.320(13) 1 d . . P A 1
O8B O -0.1301(6) 0.1818(6) 0.9643(4) 0.0220(13) Uani 0.680(13) 1 d . . P A 2
Cu1 Cu 0.21170(3) 0.48209(3) 0.60300(3) 0.01014(9) Uani 1 1 d . . . . .
Cl1 Cl 0.01984(6) 0.37010(6) 0.61341(5) 0.01473(15) Uani 1 1 d . . . . .
O1 O 0.93604(19) 1.02761(18) 0.69562(18) 0.0217(5) Uani 1 1 d . . . . .
O2 O 0.28242(18) 0.35955(17) 0.63154(16) 0.0136(4) Uani 1 1 d . . . . .
O3 O 0.1743(3) 0.4531(2) 0.42675(18) 0.0148(4) Uani 1 1 d . . . . .
H3A H 0.227(4) 0.476(3) 0.411(3) 0.016(11) Uiso 1 1 d . . . . .
H3B H 0.123(4) 0.450(4) 0.384(3) 0.036(14) Uiso 1 1 d . . . . .
N1 N 0.6980(2) 0.8466(2) 0.62572(19) 0.0131(5) Uani 1 1 d . . . . .
N2 N 0.4832(2) 0.7933(2) 0.61380(18) 0.0117(5) Uani 1 1 d . . . . .
N3 N 0.5965(2) 0.6517(2) 0.61923(17) 0.0104(5) Uani 1 1 d . . . . .
N4 N 0.3794(2) 0.5932(2) 0.61703(17) 0.0104(5) Uani 1 1 d . . . . .
N5 N 0.2717(2) 0.7266(2) 0.60688(19) 0.0130(5) Uani 1 1 d . . . . .
H5 H 0.260(3) 0.787(3) 0.602(3) 0.012(9) Uiso 1 1 d . . . . .
N6 N 0.1645(2) 0.6317(2) 0.6065(2) 0.0118(5) Uani 1 1 d . . . . .
H6A H 0.146(3) 0.652(3) 0.661(3) 0.017(9) Uiso 1 1 d . . . . .
H6B H 0.099(3) 0.622(3) 0.548(3) 0.022(9) Uiso 1 1 d . . . . .
N7 N 0.4924(2) 0.4603(2) 0.62478(18) 0.0106(5) Uani 1 1 d . . . . .
N8 N 0.6056(2) 0.4346(2) 0.62878(18) 0.0120(5) Uani 1 1 d . . . . .
C1 C 0.8223(3) 1.0520(3) 0.7030(3) 0.0217(7) Uani 1 1 d . . . . .
H1A H 0.8308 1.1343 0.6959 0.026 Uiso 1 1 calc R U . . .
H1B H 0.8120 1.0450 0.7719 0.026 Uiso 1 1 calc R U . . .
C2 C 0.7042(3) 0.9682(2) 0.6206(2) 0.0167(6) Uani 1 1 d . . . . .
H2A H 0.6266 0.9825 0.6321 0.020 Uiso 1 1 calc R U . . .
H2B H 0.7083 0.9820 0.5516 0.020 Uiso 1 1 calc R U . . .
C3 C 0.9274(3) 0.9092(3) 0.7053(2) 0.0180(6) Uani 1 1 d . . . . .
H3C H 0.9171 0.8986 0.7736 0.022 Uiso 1 1 calc R U . . .
H3D H 1.0073 0.8946 0.7006 0.022 Uiso 1 1 calc R U . . .
C4 C 0.8154(3) 0.8215(3) 0.6214(2) 0.0159(6) Uani 1 1 d . . . . .
H4A H 0.8288 0.8273 0.5532 0.019 Uiso 1 1 calc R U . . .
H4B H 0.8082 0.7401 0.6311 0.019 Uiso 1 1 calc R U . . .
C5 C 0.5891(3) 0.7624(2) 0.6188(2) 0.0111(5) Uani 1 1 d . . . . .
C6 C 0.4904(3) 0.5730(2) 0.6198(2) 0.0099(5) Uani 1 1 d . . . . .
C7 C 0.3823(3) 0.7054(2) 0.6127(2) 0.0105(5) Uani 1 1 d . . . . .
C8 C 0.3965(3) 0.3613(2) 0.6316(2) 0.0118(6) Uani 1 1 d . . . . .
C9 C 0.4517(3) 0.2739(3) 0.6403(2) 0.0132(6) Uani 1 1 d . . . . .
H9 H 0.4123 0.1956 0.6464 0.016 Uiso 1 1 calc R U . . .
C10 C 0.5781(3) 0.3235(2) 0.6384(2) 0.0122(6) Uani 1 1 d . . . . .
C11 C 0.6780(3) 0.2647(3) 0.6473(2) 0.0170(6) Uani 1 1 d . . . . .
H11A H 0.7530 0.3158 0.6336 0.026 Uiso 1 1 calc R U . . .
H11B H 0.6442 0.1892 0.5972 0.026 Uiso 1 1 calc R U . . .
H11C H 0.7025 0.2505 0.7171 0.026 Uiso 1 1 calc R U . . .
Cu2 Cu 0.16990(3) 0.54084(3) 0.86307(3) 0.01019(9) Uani 1 1 d . . . . .
Cl2 Cl 0.04746(6) 0.65374(6) 0.80789(5) 0.01419(15) Uani 1 1 d . . . . .
Cl3 Cl 0.22168(6) 0.59455(6) 1.06032(5) 0.01359(14) Uani 1 1 d . . . . .
O4 O 0.4503(2) -0.06217(18) 0.84875(17) 0.0193(5) Uani 1 1 d . . . . .
O5 O 0.32180(18) 0.64979(17) 0.84679(15) 0.0121(4) Uani 1 1 d . . . . .
N9 N 0.3764(2) 0.1390(2) 0.89243(19) 0.0118(5) Uani 1 1 d . . . . .
N10 N 0.2101(2) 0.2151(2) 0.88459(18) 0.0111(5) Uani 1 1 d . . . . .
N11 N 0.2479(2) 0.4149(2) 0.86433(18) 0.0100(5) Uani 1 1 d . . . . .
N12 N 0.4180(2) 0.3346(2) 0.88393(18) 0.0100(5) Uani 1 1 d . . . . .
N13 N 0.0521(2) 0.3015(2) 0.86651(19) 0.0120(5) Uani 1 1 d . . . . .
H13 H 0.006(3) 0.249(3) 0.888(2) 0.011(8) Uiso 1 1 d . . . . .
N14 N 0.0157(2) 0.4027(2) 0.8513(2) 0.0120(5) Uani 1 1 d . . . . .
H14A H -0.030(3) 0.414(3) 0.891(3) 0.017(9) Uiso 1 1 d . . . . .
H14B H -0.032(4) 0.387(3) 0.787(3) 0.032(11) Uiso 1 1 d . . . . .
N15 N 0.4506(2) 0.5269(2) 0.86915(18) 0.0100(5) Uani 1 1 d . . . . .
N16 N 0.5766(2) 0.5399(2) 0.87559(18) 0.0111(5) Uani 1 1 d . . . . .
C12 C 0.5195(3) 0.0486(3) 0.8329(3) 0.0205(7) Uani 1 1 d . . . . .
H12A H 0.4847 0.0542 0.7607 0.025 Uiso 1 1 calc R U . . .
H12B H 0.6102 0.0539 0.8442 0.025 Uiso 1 1 calc R U . . .
C13 C 0.3182(3) -0.0732(3) 0.8295(3) 0.0206(7) Uani 1 1 d . . . . .
H13A H 0.2711 -0.1514 0.8392 0.025 Uiso 1 1 calc R U . . .
H13B H 0.2827 -0.0689 0.7571 0.025 Uiso 1 1 calc R U . . .
C14 C 0.5111(3) 0.1503(3) 0.9052(2) 0.0164(6) Uani 1 1 d . . . . .
H14C H 0.5533 0.1497 0.9774 0.020 Uiso 1 1 calc R U . . .
H14D H 0.5554 0.2262 0.8900 0.020 Uiso 1 1 calc R U . . .
C15 C 0.2988(3) 0.0232(2) 0.9010(2) 0.0166(6) Uani 1 1 d . . . . .
H15A H 0.2075 0.0175 0.8820 0.020 Uiso 1 1 calc R U . . .
H15B H 0.3243 0.0135 0.9730 0.020 Uiso 1 1 calc R U . . .
C16 C 0.3332(3) 0.2303(2) 0.8870(2) 0.0100(5) Uani 1 1 d . . . . .
C17 C 0.1732(2) 0.3088(2) 0.8721(2) 0.0093(5) Uani 1 1 d . . . . .
C18 C 0.3683(3) 0.4186(2) 0.8724(2) 0.0089(5) Uani 1 1 d . . . . .
C19 C 0.4297(3) 0.6341(2) 0.8578(2) 0.0094(5) Uani 1 1 d . . . . .
C20 C 0.5477(3) 0.7113(2) 0.8584(2) 0.0108(5) Uani 1 1 d . . . . .
H20 H 0.5649 0.7917 0.8531 0.013 Uiso 1 1 calc R U . . .
C21 C 0.6341(3) 0.6502(2) 0.8681(2) 0.0106(5) Uani 1 1 d . . . . .
C22 C 0.7695(3) 0.6874(3) 0.8668(2) 0.0145(6) Uani 1 1 d . . . . .
H22A H 0.8152 0.6423 0.9064 0.022 Uiso 1 1 calc R U . . .
H22B H 0.8098 0.7719 0.8976 0.022 Uiso 1 1 calc R U . . .
H22C H 0.7726 0.6724 0.7954 0.022 Uiso 1 1 calc R U . . .
O6 O 1.1399(4) 1.1222(3) 0.6213(3) 0.0469(9) Uani 1 1 d . . . . .
H6C H 1.174(4) 1.190(4) 0.629(3) 0.030(11) Uiso 1 1 d . . . . .
H6D H 1.090(5) 1.114(4) 0.641(4) 0.048(16) Uiso 1 1 d . . . . .
O7 O 1.1530(3) 0.8984(3) 0.5567(2) 0.0242(5) Uani 1 1 d . . . . .
H7A H 1.091(5) 0.873(4) 0.513(4) 0.040(14) Uiso 1 1 d . . . . .
H7B H 1.157(5) 0.960(5) 0.568(4) 0.055(17) Uiso 1 1 d . . . . .
H8AA H -0.100(5) 0.199(4) 1.018(4) 0.041(16) Uiso 1 1 d . . . . .
H8AB H -0.158(6) 0.214(5) 0.955(5) 0.05(2) Uiso 1 1 d . . . . .
O10 O 0.0361(12) 0.0404(10) 0.9652(8) 0.271(5) Uani 1 1 d . . . . .
H16 H 0.609(3) 0.488(3) 0.885(3) 0.022(10) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O8A H8AA 0.87(5) . ?
O8A H8AB 1.12(5) . ?
O8B H8AA 0.70(5) . ?
O8B H8AB 0.57(5) . ?
Cu1 O2 1.910(2) . ?
Cu1 N4 1.953(2) . ?
Cu1 N6 2.018(2) . ?
Cu1 Cl1 2.2767(7) . ?
Cu1 O3 2.306(2) . ?
O1 C3 1.429(4) . ?
O1 C1 1.430(4) . ?
O2 C8 1.294(3) . ?
O3 H3A 0.69(4) . ?
O3 H3B 0.71(5) . ?
N1 C5 1.341(4) . ?
N1 C2 1.459(4) . ?
N1 C4 1.465(3) . ?
N2 C7 1.324(4) . ?
N2 C5 1.348(4) . ?
N3 C6 1.315(4) . ?
N3 C5 1.361(4) . ?
N4 C6 1.345(3) . ?
N4 C7 1.354(4) . ?
N5 C7 1.341(4) . ?
N5 N6 1.421(3) . ?
N5 H5 0.79(3) . ?
N6 H6A 0.85(4) . ?
N6 H6B 0.92(4) . ?
N7 C6 1.376(4) . ?
N7 N8 1.398(3) . ?
N7 C8 1.408(4) . ?
N8 C10 1.319(4) . ?
C1 C2 1.521(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.512(4) . ?
C3 H3C 0.9900 . ?
C3 H3D 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C8 C9 1.374(4) . ?
C9 C10 1.407(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.489(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
Cu2 O5 1.9418(19) . ?
Cu2 N11 1.962(2) . ?
Cu2 N14 2.013(2) . ?
Cu2 Cl2 2.2778(7) . ?
Cu2 Cl3 2.5706(8) . ?
O4 C12 1.424(4) . ?
O4 C13 1.429(4) . ?
O5 C19 1.272(3) . ?
N9 C16 1.328(4) . ?
N9 C15 1.466(4) . ?
N9 C14 1.468(3) . ?
N10 C17 1.327(4) . ?
N10 C16 1.355(3) . ?
N11 C18 1.337(3) . ?
N11 C17 1.359(4) . ?
N12 C18 1.301(4) . ?
N12 C16 1.369(4) . ?
N13 C17 1.341(3) . ?
N13 N14 1.418(3) . ?
N13 H13 0.83(3) . ?
N14 H14A 0.86(4) . ?
N14 H14B 0.88(4) . ?
N15 N16 1.380(3) . ?
N15 C18 1.393(4) . ?
N15 C19 1.399(3) . ?
N16 C21 1.338(4) . ?
N16 H16 0.82(4) . ?
C12 C14 1.511(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C15 1.518(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14C 0.9900 . ?
C14 H14D 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C19 C20 1.404(4) . ?
C20 C21 1.378(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.488(4) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
O6 H6C 0.78(4) . ?
O6 H6D 0.68(5) . ?
O7 H7A 0.76(5) . ?
O7 H7B 0.72(5) . ?
O10 O10 1.646(16) 2_557 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H8AA O8A H8AB 60(4) . . ?
H8AA O8B H8AB 106(7) . . ?
O2 Cu1 N4 91.94(9) . . ?
O2 Cu1 N6 166.42(10) . . ?
N4 Cu1 N6 81.45(10) . . ?
O2 Cu1 Cl1 90.43(6) . . ?
N4 Cu1 Cl1 170.32(7) . . ?
N6 Cu1 Cl1 94.23(7) . . ?
O2 Cu1 O3 100.56(9) . . ?
N4 Cu1 O3 87.85(9) . . ?
N6 Cu1 O3 91.09(9) . . ?
Cl1 Cu1 O3 100.94(7) . . ?
C3 O1 C1 110.9(2) . . ?
C8 O2 Cu1 125.16(18) . . ?
Cu1 O3 H3A 115(3) . . ?
Cu1 O3 H3B 136(4) . . ?
H3A O3 H3B 103(5) . . ?
C5 N1 C2 122.6(2) . . ?
C5 N1 C4 123.1(2) . . ?
C2 N1 C4 113.6(2) . . ?
C7 N2 C5 114.0(2) . . ?
C6 N3 C5 114.4(2) . . ?
C6 N4 C7 114.4(2) . . ?
C6 N4 Cu1 129.78(19) . . ?
C7 N4 Cu1 115.40(18) . . ?
C7 N5 N6 118.1(2) . . ?
C7 N5 H5 126(2) . . ?
N6 N5 H5 116(2) . . ?
N5 N6 Cu1 109.22(17) . . ?
N5 N6 H6A 105(2) . . ?
Cu1 N6 H6A 113(2) . . ?
N5 N6 H6B 109(2) . . ?
Cu1 N6 H6B 109(2) . . ?
H6A N6 H6B 111(3) . . ?
C6 N7 N8 119.1(2) . . ?
C6 N7 C8 129.9(2) . . ?
N8 N7 C8 110.9(2) . . ?
C10 N8 N7 104.2(2) . . ?
O1 C1 C2 112.1(2) . . ?
O1 C1 H1A 109.2 . . ?
C2 C1 H1A 109.2 . . ?
O1 C1 H1B 109.2 . . ?
C2 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
N1 C2 C1 109.0(2) . . ?
N1 C2 H2A 109.9 . . ?
C1 C2 H2A 109.9 . . ?
N1 C2 H2B 109.9 . . ?
C1 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
O1 C3 C4 110.7(2) . . ?
O1 C3 H3C 109.5 . . ?
C4 C3 H3C 109.5 . . ?
O1 C3 H3D 109.5 . . ?
C4 C3 H3D 109.5 . . ?
H3C C3 H3D 108.1 . . ?
N1 C4 C3 109.4(2) . . ?
N1 C4 H4A 109.8 . . ?
C3 C4 H4A 109.8 . . ?
N1 C4 H4B 109.8 . . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.2 . . ?
N1 C5 N2 118.5(2) . . ?
N1 C5 N3 116.0(2) . . ?
N2 C5 N3 125.5(3) . . ?
N3 C6 N4 125.7(3) . . ?
N3 C6 N7 117.6(2) . . ?
N4 C6 N7 116.6(2) . . ?
N2 C7 N5 118.7(3) . . ?
N2 C7 N4 125.8(2) . . ?
N5 C7 N4 115.4(2) . . ?
O2 C8 C9 129.7(3) . . ?
O2 C8 N7 124.7(2) . . ?
C9 C8 N7 105.6(2) . . ?
C8 C9 C10 106.2(2) . . ?
C8 C9 H9 126.9 . . ?
C10 C9 H9 126.9 . . ?
N8 C10 C9 113.1(2) . . ?
N8 C10 C11 119.9(3) . . ?
C9 C10 C11 127.0(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O5 Cu2 N11 90.89(9) . . ?
O5 Cu2 N14 166.34(9) . . ?
N11 Cu2 N14 80.60(10) . . ?
O5 Cu2 Cl2 92.52(6) . . ?
N11 Cu2 Cl2 161.34(7) . . ?
N14 Cu2 Cl2 92.30(7) . . ?
O5 Cu2 Cl3 99.27(6) . . ?
N11 Cu2 Cl3 94.16(7) . . ?
N14 Cu2 Cl3 92.03(8) . . ?
Cl2 Cu2 Cl3 103.37(3) . . ?
C12 O4 C13 110.3(2) . . ?
C19 O5 Cu2 126.25(18) . . ?
C16 N9 C15 123.1(2) . . ?
C16 N9 C14 122.5(2) . . ?
C15 N9 C14 113.9(2) . . ?
C17 N10 C16 114.6(2) . . ?
C18 N11 C17 113.0(2) . . ?
C18 N11 Cu2 130.81(19) . . ?
C17 N11 Cu2 115.50(17) . . ?
C18 N12 C16 113.9(2) . . ?
C17 N13 N14 117.3(2) . . ?
C17 N13 H13 122(2) . . ?
N14 N13 H13 119(2) . . ?
N13 N14 Cu2 110.25(17) . . ?
N13 N14 H14A 109(2) . . ?
Cu2 N14 H14A 116(2) . . ?
N13 N14 H14B 107(3) . . ?
Cu2 N14 H14B 106(3) . . ?
H14A N14 H14B 108(3) . . ?
N16 N15 C18 120.2(2) . . ?
N16 N15 C19 108.5(2) . . ?
C18 N15 C19 131.3(2) . . ?
C21 N16 N15 108.6(2) . . ?
C21 N16 H16 127(3) . . ?
N15 N16 H16 124(3) . . ?
O4 C12 C14 111.2(2) . . ?
O4 C12 H12A 109.4 . . ?
C14 C12 H12A 109.4 . . ?
O4 C12 H12B 109.4 . . ?
C14 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
O4 C13 C15 111.6(2) . . ?
O4 C13 H13A 109.3 . . ?
C15 C13 H13A 109.3 . . ?
O4 C13 H13B 109.3 . . ?
C15 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
N9 C14 C12 109.4(2) . . ?
N9 C14 H14C 109.8 . . ?
C12 C14 H14C 109.8 . . ?
N9 C14 H14D 109.8 . . ?
C12 C14 H14D 109.8 . . ?
H14C C14 H14D 108.2 . . ?
N9 C15 C13 109.3(2) . . ?
N9 C15 H15A 109.8 . . ?
C13 C15 H15A 109.8 . . ?
N9 C15 H15B 109.8 . . ?
C13 C15 H15B 109.8 . . ?
H15A C15 H15B 108.3 . . ?
N9 C16 N10 118.9(2) . . ?
N9 C16 N12 116.7(2) . . ?
N10 C16 N12 124.4(2) . . ?
N10 C17 N13 119.0(2) . . ?
N10 C17 N11 125.8(2) . . ?
N13 C17 N11 115.2(2) . . ?
N12 C18 N11 128.2(3) . . ?
N12 C18 N15 116.3(2) . . ?
N11 C18 N15 115.5(2) . . ?
O5 C19 N15 123.8(2) . . ?
O5 C19 C20 130.6(3) . . ?
N15 C19 C20 105.6(2) . . ?
C21 C20 C19 108.1(2) . . ?
C21 C20 H20 126.0 . . ?
C19 C20 H20 126.0 . . ?
N16 C21 C20 109.2(2) . . ?
N16 C21 C22 120.4(2) . . ?
C20 C21 C22 130.3(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
H6C O6 H6D 109(5) . . ?
H7A O7 H7B 101(5) . . ?

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
O3 H3A N8 0.69(4) 2.15(4) 2.830(3) 173(4) 2_666
O3 H3B Cl2 0.71(5) 2.74(5) 3.395(3) 153(4) 2_566
N5 H5 O7 0.79(3) 2.10(4) 2.842(4) 156(3) 1_455
N6 H6A Cl2 0.85(4) 2.53(4) 3.351(3) 163(3) .
N6 H6B Cl1 0.92(4) 2.33(4) 3.220(3) 163(3) 2_566
N13 H13 O8A 0.83(3) 2.07(4) 2.887(14) 168(3) .
N13 H13 O8B 0.83(3) 2.12(3) 2.894(6) 155(3) .
N14 H14A Cl3 0.86(4) 2.41(4) 3.226(2) 158(3) 2_567
N14 H14B Cl1 0.88(4) 2.58(4) 3.240(3) 132(3) .
O6 H6C O2 0.78(4) 2.07(5) 2.835(4) 169(4) 1_665
O6 H6D O1 0.68(5) 2.13(5) 2.777(4) 160(5) .
O7 H7A Cl1 0.76(5) 2.95(5) 3.467(3) 127(4) 2_666
O7 H7B O6 0.72(5) 2.08(5) 2.783(4) 166(6) .
O8A H8AA Cl2 0.87(5) 2.61(5) 3.471(14) 171(4) 2_567
O8B H8AA Cl2 0.70(5) 2.61(5) 3.232(6) 148(5) 2_567
O8A H8AB Cl3 1.12(5) 2.63(6) 3.718(14) 165(5) 2_567
O8B H8AB Cl3 0.57(5) 2.63(6) 3.179(8) 164(7) 2_567
N16 H16 Cl3 0.82(4) 2.42(4) 3.187(2) 157(3) 2_667

_refine_diff_density_max         2.201
_refine_diff_density_min         -1.005
_refine_diff_density_rms         0.097

####################################################################### 
# 
# 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_Complex-8
_database_code_depnum_ccdc_archive 'CCDC 1555237'
_audit_update_record             
;
2017-06-09 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT430_Complex-8           
;
PROBLEM: Short Inter D...A Contact  
RESPONSE: The crystals of this complex were small sized with poor X-ray 
 diffraction and repeated recrystallization under different environments
 did not gave better quality crystals. These alerts arise 
 because of large number of disordered solvate water molecules with multiple
 occupancies. Due to poor quality of X-ray diffraction data, most of solvent
 disorders could not be modeled. 	
;
_vrf_PLAT306_Complex-8           
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) .......         O6 Check   
RESPONSE: The hydrogen atoms associated with the disordered solvate 
 water molecules with multiple occupancies could not be located 
 in the difference density map.    	
;
_vrf_PLAT430_B_Complex-8         
;
PROBLEM: Short Inter D...A Contact  
RESPONSE: These alerts arise  because of large number of disordered solvate
 water molecules with multiple occupancies. PLATON/SQUEEZE option was not used
 because the total number of  disorderd solvate molecules was not ascertained.    	
;
_vrf_PLAT431_Complex-8           
;
PROBLEM: Short Inter HL..A  Contact Cl2    ..  O13B 
RESPONSE: This is again due to the disordered solvate molecules.      	
;

_audit_creation_date             2017-08-06
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            none
_chemical_melting_point          'not measured'
_chemical_formula_moiety         
'C22 H31 N16 O4 Zn, 0.497(O3), Cl, H2 O, 6.5(O)'
_chemical_formula_sum            'C22 H33 Cl N16 O13 Zn'
_chemical_formula_weight         830.48

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                   12.4036(8)
_cell_length_b                   19.8086(13)
_cell_length_c                   14.3748(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.559(2)
_cell_angle_gamma                90
_cell_volume                     3530.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9902
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      26.40

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_F_000             1712
_exptl_transmission_factor_min   0.961
_exptl_transmission_factor_max   0.974
_exptl_crystal_size_max          0.326
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.105
_exptl_absorpt_coefficient_mu    0.855
_shelx_estimated_absorpt_T_min   0.768
_shelx_estimated_absorpt_T_max   0.916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_T_max  0.914
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0826 before and 0.0742 after correction. The Ratio of minimum to maximum transmission is 0.8679. The λ/2 correction factor is 0.00150.'
;
_exptl_absorpt_special_details   
;
 The crystal was mounted using Paratone-N oil (cryoprotectant)
 on the tip of MiTeGen MicroLoops LD?. It was placed on magnetic 
 head of goniometer directly into the cold gas stream of a 
 liquid-nitrogen based cryostat.
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focused sealed tube'
_diffrn_measurement_device_type  
;
 Bruker D8 Quest with Photon 100 CMOS Detector
;
_diffrn_measurement_method       
;
 φ and ω scans with 0.5 deg/frame and 20 seconds of
 exposure time. Detector was at 50mm from crystal.
;
_diffrn_detector                 'Photon 100 CMOS detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            123887
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_av_R_equivalents  0.1068
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.968
_diffrn_reflns_theta_max         27.167
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7821
_reflns_number_gt                5705
_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       'Apex3 (Bruker AXS Inc., 2016)'
_computing_cell_refinement       'Apex3 (Bruker AXS Inc., 2016)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
 ORTEp-3 (Farrugia, 2012) and Olex2 (Dolomanov et al., 2009)
;
_computing_publication_material  'WinGX2014.1 (Farrugia, 2012)'
_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)+(0.0145P)²+24.9549P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     mixed
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7821
_refine_ls_number_parameters     532
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1249
_refine_ls_R_factor_gt           0.0864
_refine_ls_wR_factor_ref         0.1760
_refine_ls_wR_factor_gt          0.1627
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_restrained_S_all      1.193
_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
O13A O 0.792(3) 0.2507(8) 0.9387(14) 0.160(7) Uani 0.497(7) 1 d . . P A 1
O13B O 0.817(2) 0.2731(8) 1.0269(12) 0.160(7) Uani 0.503(7) 1 d . . P A 2
Zn1 Zn 0.15124(5) 0.53094(3) 0.72352(4) 0.02037(17) Uani 1 1 d . . . . .
O1 O 0.8147(3) 0.4817(2) 0.9636(3) 0.0287(9) Uani 1 1 d . . . . .
O2 O 0.2147(3) 0.5628(2) 0.5996(3) 0.0240(9) Uani 1 1 d . . . . .
O3 O 0.1357(3) 0.43050(18) 0.6921(2) 0.0200(8) Uani 1 1 d . . . . .
O4 O -0.5234(3) 0.5966(2) 0.5149(3) 0.0338(10) Uani 1 1 d . . . . .
N1 N 0.6087(3) 0.4935(2) 0.8787(3) 0.0245(11) Uani 1 1 d . . . . .
N2 N 0.4595(3) 0.5592(2) 0.8500(3) 0.0207(10) Uani 1 1 d . . . . .
N3 N 0.3028(3) 0.5074(2) 0.7803(3) 0.0177(9) Uani 1 1 d . . . . .
N4 N 0.4575(3) 0.4406(2) 0.8159(3) 0.0198(10) Uani 1 1 d . . . . .
N5 N 0.3119(3) 0.6214(2) 0.8144(3) 0.0227(10) Uani 1 1 d . . . . .
N6 N 0.2050(4) 0.6290(3) 0.7777(4) 0.0256(11) Uani 1 1 d . . . . .
N7 N 0.3035(3) 0.3913(2) 0.7559(3) 0.0196(10) Uani 1 1 d . . . . .
N8 N 0.3562(4) 0.3289(2) 0.7675(4) 0.0288(11) Uani 1 1 d . . . . .
N9 N -0.3095(3) 0.5675(2) 0.5723(3) 0.0198(10) Uani 1 1 d . . . . .
N10 N -0.1285(3) 0.5779(2) 0.5423(3) 0.0170(9) Uani 1 1 d . . . . .
N11 N -0.1882(3) 0.5424(2) 0.6914(3) 0.0210(10) Uani 1 1 d . . . . .
N12 N -0.0002(3) 0.5512(2) 0.6622(3) 0.0172(9) Uani 1 1 d . . . . .
N13 N 0.0531(3) 0.5834(2) 0.5156(3) 0.0190(9) Uani 1 1 d . . . . .
N14 N 0.0276(3) 0.6112(2) 0.4290(3) 0.0193(10) Uani 1 1 d . . . . .
N15 N -0.0624(3) 0.5173(2) 0.8040(3) 0.0228(11) Uani 1 1 d . . . . .
N16 N 0.0455(3) 0.5168(3) 0.8399(3) 0.0221(10) Uani 1 1 d . . . . .
C1 C 0.7524(4) 0.4229(3) 0.9446(4) 0.0298(14) Uani 1 1 d . . . . .
H1A H 0.7115 0.4108 1.0003 0.036 Uiso 1 1 calc R U . . .
H1B H 0.8013 0.3848 0.9308 0.036 Uiso 1 1 calc R U . . .
C2 C 0.7457(4) 0.5372(3) 0.9852(4) 0.0290(13) Uani 1 1 d . . . . .
H2A H 0.7903 0.5773 1.0005 0.035 Uiso 1 1 calc R U . . .
H2B H 0.7035 0.5258 1.0405 0.035 Uiso 1 1 calc R U . . .
C3 C 0.6691(4) 0.5538(3) 0.9046(4) 0.0250(13) Uani 1 1 d . . . . .
H3A H 0.6189 0.5900 0.9229 0.030 Uiso 1 1 calc R U . . .
H3B H 0.7103 0.5700 0.8510 0.030 Uiso 1 1 calc R U . . .
C4 C 0.6739(4) 0.4334(3) 0.8622(4) 0.0257(13) Uani 1 1 d . . . . .
H4A H 0.7145 0.4391 0.8043 0.031 Uiso 1 1 calc R U . . .
H4B H 0.6265 0.3934 0.8547 0.031 Uiso 1 1 calc R U . . .
C5 C 0.5047(4) 0.4978(3) 0.8471(4) 0.0193(11) Uani 1 1 d . . . . .
C6 C 0.3570(4) 0.4488(3) 0.7850(4) 0.0184(11) Uani 1 1 d . . . . .
C7 C 0.3587(4) 0.5607(3) 0.8146(3) 0.0185(11) Uani 1 1 d . . . . .
C8 C 0.1996(4) 0.3822(3) 0.7143(4) 0.0213(12) Uani 1 1 d . . . . .
C9 C 0.1896(4) 0.3136(3) 0.7014(4) 0.0297(14) Uani 1 1 d . . . . .
H9 H 0.1288 0.2908 0.6750 0.036 Uiso 1 1 calc R U . . .
C10 C 0.2858(5) 0.2838(3) 0.7342(5) 0.0321(14) Uani 1 1 d . . . . .
C11 C 0.3120(6) 0.2104(3) 0.7354(6) 0.049(2) Uani 1 1 d . . . . .
H11A H 0.3895 0.2044 0.7266 0.074 Uiso 1 1 calc R U . . .
H11B H 0.2715 0.1877 0.6850 0.074 Uiso 1 1 calc R U . . .
H11C H 0.2923 0.1910 0.7952 0.074 Uiso 1 1 calc R U . . .
C12 C 0.1660(4) 0.5825(3) 0.5270(4) 0.0198(11) Uani 1 1 d . . . . .
C13 C 0.2069(4) 0.6090(3) 0.4446(4) 0.0201(11) Uani 1 1 d . . . . .
H13 H 0.2810 0.6150 0.4316 0.024 Uiso 1 1 calc R U . . .
C14 C 0.1215(4) 0.6247(3) 0.3861(4) 0.0194(11) Uani 1 1 d . . . . .
C15 C 0.1209(4) 0.6539(3) 0.2915(4) 0.0246(12) Uani 1 1 d . . . . .
H15A H 0.0831 0.6232 0.2482 0.037 Uiso 1 1 calc R U . . .
H15B H 0.1953 0.6601 0.2719 0.037 Uiso 1 1 calc R U . . .
H15C H 0.0839 0.6976 0.2917 0.037 Uiso 1 1 calc R U . . .
C16 C -0.0292(4) 0.5705(3) 0.5763(4) 0.0162(11) Uani 1 1 d . . . . .
C17 C -0.0839(4) 0.5378(3) 0.7169(4) 0.0193(11) Uani 1 1 d . . . . .
C18 C -0.2065(4) 0.5622(3) 0.6036(4) 0.0175(11) Uani 1 1 d . . . . .
C19 C -0.3372(4) 0.5807(3) 0.4744(4) 0.0263(13) Uani 1 1 d . . . . .
H19A H -0.3518 0.5376 0.4416 0.032 Uiso 1 1 calc R U . . .
H19B H -0.2759 0.6032 0.4443 0.032 Uiso 1 1 calc R U . . .
C20 C -0.4355(4) 0.6253(4) 0.4677(5) 0.0393(17) Uani 1 1 d . . . . .
H20A H -0.4181 0.6700 0.4949 0.047 Uiso 1 1 calc R U . . .
H20B H -0.4564 0.6320 0.4013 0.047 Uiso 1 1 calc R U . . .
C21 C -0.4968(4) 0.5880(4) 0.6112(4) 0.0352(15) Uani 1 1 d . . . . .
H21A H -0.5592 0.5682 0.6428 0.042 Uiso 1 1 calc R U . . .
H21B H -0.4817 0.6327 0.6395 0.042 Uiso 1 1 calc R U . . .
C22 C -0.3998(4) 0.5429(3) 0.6262(4) 0.0306(14) Uani 1 1 d . . . . .
H22A H -0.3788 0.5421 0.6931 0.037 Uiso 1 1 calc R U . . .
H22B H -0.4182 0.4963 0.6068 0.037 Uiso 1 1 calc R U . . .
Cl2 Cl 0.0088(2) 0.32187(10) 1.10412(15) 0.0662(7) Uani 1 1 d . . . . .
O5 O 0.0468(4) 0.3766(3) 0.9002(4) 0.0470(13) Uani 1 1 d D . . . .
O6 O 0.3931(5) 0.1917(3) 0.4726(4) 0.0702(18) Uani 1 1 d . . . . .
O7 O 0.5790(5) 0.2250(3) 0.5782(4) 0.0627(16) Uani 1 1 d . . . . .
O8 O 0.5773(4) 0.2872(3) 0.7541(4) 0.0533(14) Uani 1 1 d . . . . .
O9A O 0.6707(19) 0.2186(11) 0.8935(14) 0.103(9) Uani 0.497(7) 1 d . . P A 1
O9B O 0.6611(10) 0.2388(12) 0.9277(12) 0.095(8) Uani 0.503(7) 1 d . . P A 2
O10A O 0.8890(11) 0.2427(7) 0.9196(10) 0.066(2) Uani 0.497(7) 1 d . . P A 1
O10B O 0.8350(10) 0.2288(7) 0.8700(9) 0.066(2) Uani 0.503(7) 1 d . . P A 2
O11 O 1.0475(6) 0.2116(4) 0.8313(5) 0.088(2) Uani 1 1 d . . . . .
O12 O 1.1909(6) 0.2444(4) 0.9733(5) 0.095(2) Uani 1 1 d . . . . .
H5 H 0.348(5) 0.658(3) 0.835(4) 0.028(17) Uiso 1 1 d . . . . .
H6A H 0.169(4) 0.649(3) 0.819(4) 0.014(15) Uiso 1 1 d . . . . .
H6B H 0.202(5) 0.658(4) 0.730(5) 0.04(2) Uiso 1 1 d . . . . .
H15 H -0.111(4) 0.510(3) 0.839(4) 0.014(14) Uiso 1 1 d . . . . .
H16A H 0.046(4) 0.550(3) 0.886(3) 0.003(12) Uiso 1 1 d . . . . .
H16B H 0.056(4) 0.479(3) 0.861(4) 0.018(16) Uiso 1 1 d . . . . .
H5A H 0.031(4) 0.364(3) 0.965(4) 0.019(15) Uiso 1 1 d D . . . .
H14 H -0.027(6) 0.598(4) 0.403(5) 0.05(2) Uiso 1 1 d . . . . .
H5B H 0.07(3) 0.334(5) 0.871(10) 0.7(3) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O13A O10A 1.25(3) . ?
O13A O9A 1.74(3) . ?
Zn1 O3 2.048(4) . ?
Zn1 O2 2.066(4) . ?
Zn1 N3 2.082(4) . ?
Zn1 N12 2.092(4) . ?
Zn1 N16 2.172(5) . ?
Zn1 N6 2.191(5) . ?
O1 C1 1.421(7) . ?
O1 C2 1.432(7) . ?
O2 C12 1.253(6) . ?
O3 C8 1.277(6) . ?
O4 C20 1.418(7) . ?
O4 C21 1.425(7) . ?
N1 C5 1.358(6) . ?
N1 C3 1.454(7) . ?
N1 C4 1.462(7) . ?
N2 C7 1.338(6) . ?
N2 C5 1.340(7) . ?
N3 C6 1.343(7) . ?
N3 C7 1.348(7) . ?
N4 C6 1.322(6) . ?
N4 C5 1.347(7) . ?
N5 C7 1.334(7) . ?
N5 N6 1.421(6) . ?
N5 H5 0.89(6) . ?
N6 H6A 0.85(6) . ?
N6 H6B 0.90(7) . ?
N7 C6 1.378(7) . ?
N7 N8 1.405(6) . ?
N7 C8 1.417(6) . ?
N8 C10 1.331(7) . ?
N9 C18 1.346(6) . ?
N9 C22 1.463(7) . ?
N9 C19 1.463(7) . ?
N10 C16 1.321(6) . ?
N10 C18 1.363(7) . ?
N11 C18 1.336(7) . ?
N11 C17 1.338(6) . ?
N12 C16 1.332(6) . ?
N12 C17 1.345(7) . ?
N13 C16 1.385(7) . ?
N13 N14 1.390(6) . ?
N13 C12 1.406(6) . ?
N14 C14 1.360(7) . ?
N14 H14 0.81(7) . ?
N15 C17 1.336(7) . ?
N15 N16 1.422(6) . ?
N15 H15 0.81(6) . ?
N16 H16A 0.93(5) . ?
N16 H16B 0.81(6) . ?
C1 C4 1.527(7) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.514(7) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C8 C9 1.377(8) . ?
C9 C10 1.402(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.488(9) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.403(8) . ?
C13 C14 1.371(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.477(7) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C19 C20 1.507(8) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.509(8) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
O5 H5A 0.99(6) . ?
O5 H5B 0.99(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
O10A O13A O9A 134.2(17) . . ?
O3 Zn1 O2 98.17(15) . . ?
O3 Zn1 N3 87.01(15) . . ?
O2 Zn1 N3 92.59(15) . . ?
O3 Zn1 N12 90.89(15) . . ?
O2 Zn1 N12 86.38(15) . . ?
N3 Zn1 N12 177.51(18) . . ?
O3 Zn1 N16 89.43(18) . . ?
O2 Zn1 N16 162.92(16) . . ?
N3 Zn1 N16 103.11(17) . . ?
N12 Zn1 N16 78.19(16) . . ?
O3 Zn1 N6 165.00(15) . . ?
O2 Zn1 N6 85.21(19) . . ?
N3 Zn1 N6 78.21(17) . . ?
N12 Zn1 N6 103.94(17) . . ?
N16 Zn1 N6 91.4(2) . . ?
C1 O1 C2 110.3(4) . . ?
C12 O2 Zn1 128.8(3) . . ?
C8 O3 Zn1 128.2(3) . . ?
C20 O4 C21 110.6(4) . . ?
C5 N1 C3 120.8(5) . . ?
C5 N1 C4 121.5(4) . . ?
C3 N1 C4 115.3(4) . . ?
C7 N2 C5 113.4(4) . . ?
C6 N3 C7 114.0(4) . . ?
C6 N3 Zn1 131.2(3) . . ?
C7 N3 Zn1 114.7(3) . . ?
C6 N4 C5 113.9(4) . . ?
C7 N5 N6 119.9(5) . . ?
C7 N5 H5 121(4) . . ?
N6 N5 H5 119(4) . . ?
N5 N6 Zn1 108.0(3) . . ?
N5 N6 H6A 107(4) . . ?
Zn1 N6 H6A 120(4) . . ?
N5 N6 H6B 112(4) . . ?
Zn1 N6 H6B 107(4) . . ?
H6A N6 H6B 103(6) . . ?
C6 N7 N8 118.1(4) . . ?
C6 N7 C8 131.1(4) . . ?
N8 N7 C8 110.7(4) . . ?
C10 N8 N7 104.4(4) . . ?
C18 N9 C22 122.0(4) . . ?
C18 N9 C19 122.1(4) . . ?
C22 N9 C19 113.9(4) . . ?
C16 N10 C18 114.0(4) . . ?
C18 N11 C17 114.7(4) . . ?
C16 N12 C17 113.8(4) . . ?
C16 N12 Zn1 131.5(3) . . ?
C17 N12 Zn1 114.5(3) . . ?
C16 N13 N14 118.9(4) . . ?
C16 N13 C12 132.3(4) . . ?
N14 N13 C12 108.1(4) . . ?
C14 N14 N13 107.9(4) . . ?
C14 N14 H14 125(5) . . ?
N13 N14 H14 117(5) . . ?
C17 N15 N16 120.3(5) . . ?
C17 N15 H15 121(4) . . ?
N16 N15 H15 119(4) . . ?
N15 N16 Zn1 107.5(3) . . ?
N15 N16 H16A 104(3) . . ?
Zn1 N16 H16A 118(3) . . ?
N15 N16 H16B 107(4) . . ?
Zn1 N16 H16B 108(4) . . ?
H16A N16 H16B 113(5) . . ?
O1 C1 C4 111.7(5) . . ?
O1 C1 H1A 109.3 . . ?
C4 C1 H1A 109.3 . . ?
O1 C1 H1B 109.3 . . ?
C4 C1 H1B 109.3 . . ?
H1A C1 H1B 107.9 . . ?
O1 C2 C3 111.6(5) . . ?
O1 C2 H2A 109.3 . . ?
C3 C2 H2A 109.3 . . ?
O1 C2 H2B 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
N1 C3 C2 109.0(5) . . ?
N1 C3 H3A 109.9 . . ?
C2 C3 H3A 109.9 . . ?
N1 C3 H3B 109.9 . . ?
C2 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
N1 C4 C1 109.3(5) . . ?
N1 C4 H4A 109.8 . . ?
C1 C4 H4A 109.8 . . ?
N1 C4 H4B 109.8 . . ?
C1 C4 H4B 109.8 . . ?
H4A C4 H4B 108.3 . . ?
N2 C5 N4 126.5(4) . . ?
N2 C5 N1 116.2(5) . . ?
N4 C5 N1 117.3(5) . . ?
N4 C6 N3 126.1(5) . . ?
N4 C6 N7 116.3(5) . . ?
N3 C6 N7 117.6(4) . . ?
N5 C7 N2 115.0(5) . . ?
N5 C7 N3 119.0(4) . . ?
N2 C7 N3 125.9(5) . . ?
O3 C8 C9 130.7(5) . . ?
O3 C8 N7 124.2(5) . . ?
C9 C8 N7 105.0(5) . . ?
C8 C9 C10 107.4(5) . . ?
C8 C9 H9 126.3 . . ?
C10 C9 H9 126.3 . . ?
N8 C10 C9 112.4(5) . . ?
N8 C10 C11 120.7(5) . . ?
C9 C10 C11 126.8(5) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 C13 129.9(5) . . ?
O2 C12 N13 123.9(5) . . ?
C13 C12 N13 106.2(4) . . ?
C14 C13 C12 108.2(4) . . ?
C14 C13 H13 125.9 . . ?
C12 C13 H13 125.9 . . ?
N14 C14 C13 109.5(5) . . ?
N14 C14 C15 120.8(4) . . ?
C13 C14 C15 129.7(5) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N10 C16 N12 126.9(5) . . ?
N10 C16 N13 116.2(4) . . ?
N12 C16 N13 116.8(4) . . ?
N15 C17 N11 116.4(5) . . ?
N15 C17 N12 118.0(4) . . ?
N11 C17 N12 125.6(5) . . ?
N11 C18 N9 118.3(5) . . ?
N11 C18 N10 124.9(4) . . ?
N9 C18 N10 116.8(4) . . ?
N9 C19 C20 109.6(5) . . ?
N9 C19 H19A 109.8 . . ?
C20 C19 H19A 109.8 . . ?
N9 C19 H19B 109.8 . . ?
C20 C19 H19B 109.8 . . ?
H19A C19 H19B 108.2 . . ?
O4 C20 C19 111.5(5) . . ?
O4 C20 H20A 109.3 . . ?
C19 C20 H20A 109.3 . . ?
O4 C20 H20B 109.3 . . ?
C19 C20 H20B 109.3 . . ?
H20A C20 H20B 108.0 . . ?
O4 C21 C22 111.8(5) . . ?
O4 C21 H21A 109.2 . . ?
C22 C21 H21A 109.2 . . ?
O4 C21 H21B 109.2 . . ?
C22 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?
N9 C22 C21 110.3(5) . . ?
N9 C22 H22A 109.6 . . ?
C21 C22 H22A 109.6 . . ?
N9 C22 H22B 109.6 . . ?
C21 C22 H22B 109.6 . . ?
H22A C22 H22B 108.1 . . ?
H5A O5 H5B 104(6) . . ?

_refine_diff_density_max         1.216
_refine_diff_density_min         -1.062
_refine_diff_density_rms         0.112

