# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1545172'
_audit_update_record             
;
2017-04-20 deposited with the CCDC.
2017-06-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H52 N6 O2 Zn'
_chemical_formula_weight         738.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2840 1.4300 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/c'
_space_group_name_Hall           '-P 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, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   14.0610(8)
_cell_length_b                   8.9270(3)
_cell_length_c                   19.1620(9)
_cell_angle_alpha                90
_cell_angle_beta                 129.338(2)
_cell_angle_gamma                90
_cell_volume                     1860.28(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3550
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.705
_shelx_estimated_absorpt_T_min   0.844
_shelx_estimated_absorpt_T_max   0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.844
_exptl_absorpt_correction_T_max  0.932
_exptl_absorpt_process_details   'Scalepak (Otwinowski, Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa-CCD'
_diffrn_measurement_method       'area detector ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6104
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.664
_diffrn_reflns_theta_max         25.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3623
_reflns_number_gt                3158
_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       KappaCCD
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0380P)²+4.2066P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3623
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_ref         0.1255
_refine_ls_wR_factor_gt          0.1181
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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
C1 C 0.0166(3) 0.3806(4) 0.3778(2) 0.0300(7) Uani 1 1 d . . . . .
H1A H -0.031388 0.471042 0.365323 0.045 Uiso 1 1 calc R U . . .
H1B H 0.022946 0.319911 0.423259 0.045 Uiso 1 1 calc R U . . .
H1C H -0.024222 0.322299 0.322217 0.045 Uiso 1 1 calc R U . . .
C2 C 0.1462(3) 0.4252(4) 0.4135(2) 0.0252(6) Uani 1 1 d . . . . .
C3 C 0.2148(3) 0.5194(3) 0.4998(2) 0.0225(6) Uani 1 1 d . . . . .
C4 C 0.1781(3) 0.5356(4) 0.5519(2) 0.0312(7) Uani 1 1 d . . . . .
H4 H 0.107063 0.484034 0.534861 0.037 Uiso 1 1 calc R U . . .
C5 C 0.2432(3) 0.6257(4) 0.6284(2) 0.0333(7) Uani 1 1 d . . . . .
H5 H 0.215853 0.635925 0.662493 0.040 Uiso 1 1 calc R U . . .
C6 C 0.3472(3) 0.7004(4) 0.6549(2) 0.0303(7) Uani 1 1 d . . . . .
H6 H 0.390846 0.763431 0.706530 0.036 Uiso 1 1 calc R U . . .
C7 C 0.3876(3) 0.6826(4) 0.6056(2) 0.0306(7) Uani 1 1 d . . . . .
H7 H 0.460501 0.731386 0.624363 0.037 Uiso 1 1 calc R U . . .
C8 C 0.3217(3) 0.5940(3) 0.5289(2) 0.0269(7) Uani 1 1 d . . . . .
H8 H 0.349953 0.583558 0.495403 0.032 Uiso 1 1 calc R U . . .
C9 C 0.2197(3) 0.2803(3) 0.4350(2) 0.0229(6) Uani 1 1 d . . . . .
C10 C 0.2471(3) 0.1836(3) 0.5030(2) 0.0253(6) Uani 1 1 d . . . . .
H10 H 0.223744 0.210522 0.538220 0.030 Uiso 1 1 calc R U . . .
C11 C 0.3076(3) 0.0493(4) 0.5198(2) 0.0292(7) Uani 1 1 d . . . . .
H11 H 0.324362 -0.015680 0.565650 0.035 Uiso 1 1 calc R U . . .
C12 C 0.3436(3) 0.0096(4) 0.4697(2) 0.0333(8) Uani 1 1 d . . . . .
H12 H 0.384839 -0.082564 0.480696 0.040 Uiso 1 1 calc R U . . .
C13 C 0.3190(3) 0.1057(4) 0.4037(2) 0.0358(8) Uani 1 1 d . . . . .
H13 H 0.344604 0.079725 0.369803 0.043 Uiso 1 1 calc R U . . .
C14 C 0.2574(3) 0.2397(4) 0.3860(2) 0.0305(7) Uani 1 1 d . . . . .
H14 H 0.240861 0.304050 0.339932 0.037 Uiso 1 1 calc R U . . .
C15 C 0.0061(3) 0.8696(4) 0.3535(3) 0.0440(10) Uani 1 1 d . . . . .
H15A H 0.089367 0.825305 0.395501 0.053 Uiso 1 1 calc R U . . .
H15B H 0.010616 0.954890 0.322705 0.053 Uiso 1 1 calc R U . . .
C16 C -0.0285(4) 0.9262(5) 0.4057(3) 0.0515(11) Uani 1 1 d . . . . .
H16A H 0.022543 1.014439 0.441218 0.062 Uiso 1 1 calc R U . . .
H16B H -0.013811 0.848128 0.448287 0.062 Uiso 1 1 calc R U . . .
C17 C -0.1657(3) 0.9707(3) 0.3420(2) 0.0305(7) Uani 1 1 d . . . . .
H17A H -0.191562 0.998130 0.377796 0.037 Uiso 1 1 calc R U . . .
H17B H -0.178454 1.058653 0.305399 0.037 Uiso 1 1 calc R U . . .
C18 C -0.3693(3) 0.8457(3) 0.2403(2) 0.0258(7) Uani 1 1 d . . . . .
H18A H -0.412512 0.920572 0.191003 0.031 Uiso 1 1 calc R U . . .
H18B H -0.378933 0.875461 0.285247 0.031 Uiso 1 1 calc R U . . .
C19 C -0.4267(3) 0.6940(4) 0.2026(2) 0.0284(7) Uani 1 1 d . . . . .
H19A H -0.516717 0.699849 0.168081 0.034 Uiso 1 1 calc R U . . .
H19B H -0.392317 0.621142 0.252273 0.034 Uiso 1 1 calc R U . . .
C20 C -0.3995(3) 0.6439(4) 0.1412(2) 0.0286(7) Uani 1 1 d . . . . .
H20A H -0.430268 0.540671 0.119656 0.034 Uiso 1 1 calc R U . . .
H20B H -0.441619 0.710733 0.088044 0.034 Uiso 1 1 calc R U . . .
C21 C -0.1923(3) 0.7529(3) 0.2536(2) 0.0217(6) Uani 1 1 d . . . . .
O1 O 0.13826(19) 0.5063(2) 0.34745(14) 0.0271(5) Uani 1 1 d . . . . .
N1 N -0.0778(2) 0.7569(3) 0.28572(18) 0.0263(6) Uani 1 1 d . . . . .
N2 N -0.2391(2) 0.8448(3) 0.28281(17) 0.0244(6) Uani 1 1 d . . . . .
N3 N -0.2679(2) 0.6485(3) 0.19070(17) 0.0255(6) Uani 1 1 d . . . . .
H3 H -0.235205 0.579188 0.179063 0.031 Uiso 1 1 calc R U . . .
ZN1 Zn 0.000000 0.62179(5) 0.250000 0.02029(15) Uani 1 2 d S T P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.538(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O1 1.400(4) . ?
C2 C3 1.533(4) . ?
C2 C9 1.540(4) . ?
C3 C4 1.393(4) . ?
C3 C8 1.397(4) . ?
C4 C5 1.389(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.378(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.386(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.384(5) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C14 1.388(4) . ?
C9 C10 1.398(4) . ?
C10 C11 1.385(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.378(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.387(5) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.452(6) . ?
C15 N1 1.465(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.544(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 N2 1.460(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 N2 1.457(4) . ?
C18 C19 1.506(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.517(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 N3 1.449(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 N1 1.311(4) . ?
C21 N3 1.351(4) . ?
C21 N2 1.373(4) . ?
O1 ZN1 1.931(2) . ?
N1 ZN1 2.017(3) . ?
N3 H3 0.8800 . ?
ZN1 O1 1.931(2) 2 ?
ZN1 N1 2.017(3) 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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 109.0(2) . . ?
O1 C2 C1 109.8(2) . . ?
C3 C2 C1 112.3(3) . . ?
O1 C2 C9 109.3(2) . . ?
C3 C2 C9 108.4(2) . . ?
C1 C2 C9 107.8(3) . . ?
C4 C3 C8 117.3(3) . . ?
C4 C3 C2 124.4(3) . . ?
C8 C3 C2 118.4(3) . . ?
C5 C4 C3 121.4(3) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 119.4(3) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C8 C7 C6 120.1(3) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C3 121.6(3) . . ?
C7 C8 H8 119.2 . . ?
C3 C8 H8 119.2 . . ?
C14 C9 C10 118.1(3) . . ?
C14 C9 C2 121.2(3) . . ?
C10 C9 C2 120.6(3) . . ?
C11 C10 C9 121.1(3) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 120.1(3) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 119.1(3) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C14 121.1(3) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C13 C14 C9 120.4(3) . . ?
C13 C14 H14 119.8 . . ?
C9 C14 H14 119.8 . . ?
C16 C15 N1 114.6(3) . . ?
C16 C15 H15A 108.6 . . ?
N1 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
N1 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
C15 C16 C17 109.9(3) . . ?
C15 C16 H16A 109.7 . . ?
C17 C16 H16A 109.7 . . ?
C15 C16 H16B 109.7 . . ?
C17 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
N2 C17 C16 109.2(3) . . ?
N2 C17 H17A 109.8 . . ?
C16 C17 H17A 109.8 . . ?
N2 C17 H17B 109.8 . . ?
C16 C17 H17B 109.8 . . ?
H17A C17 H17B 108.3 . . ?
N2 C18 C19 111.4(2) . . ?
N2 C18 H18A 109.3 . . ?
C19 C18 H18A 109.3 . . ?
N2 C18 H18B 109.3 . . ?
C19 C18 H18B 109.3 . . ?
H18A C18 H18B 108.0 . . ?
C18 C19 C20 108.3(3) . . ?
C18 C19 H19A 110.0 . . ?
C20 C19 H19A 110.0 . . ?
C18 C19 H19B 110.0 . . ?
C20 C19 H19B 110.0 . . ?
H19A C19 H19B 108.4 . . ?
N3 C20 C19 109.2(3) . . ?
N3 C20 H20A 109.8 . . ?
C19 C20 H20A 109.8 . . ?
N3 C20 H20B 109.8 . . ?
C19 C20 H20B 109.8 . . ?
H20A C20 H20B 108.3 . . ?
N1 C21 N3 118.4(3) . . ?
N1 C21 N2 123.8(3) . . ?
N3 C21 N2 117.8(3) . . ?
C2 O1 ZN1 127.22(18) . . ?
C21 N1 C15 119.6(3) . . ?
C21 N1 ZN1 126.4(2) . . ?
C15 N1 ZN1 114.0(2) . . ?
C21 N2 C18 122.1(3) . . ?
C21 N2 C17 119.4(3) . . ?
C18 N2 C17 116.7(2) . . ?
C21 N3 C20 124.0(3) . . ?
C21 N3 H3 118.0 . . ?
C20 N3 H3 118.0 . . ?
O1 ZN1 O1 115.44(14) . 2 ?
O1 ZN1 N1 114.92(10) . . ?
O1 ZN1 N1 102.56(9) 2 . ?
O1 ZN1 N1 102.56(9) . 2 ?
O1 ZN1 N1 114.92(10) 2 2 ?
N1 ZN1 N1 106.53(15) . 2 ?


_refine_diff_density_max         1.482
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.075

####################################################################### 
# 
# 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_shelx_comp2
_database_code_depnum_ccdc_archive 'CCDC 1545171'
_audit_update_record             
;
2017-04-20 deposited with the CCDC.
2017-06-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C64 H116 N24 O4 Zn10'
_chemical_formula_weight         1939.50

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'
O O 0.0106 0.0060 '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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           86
_space_group_name_H-M_alt        'P 42/n'
_space_group_name_Hall           '-P 4bc'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-y, x+1/2, z+1/2'
'y+1/2, -x, z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'y, -x-1/2, -z-1/2'
'-y-1/2, x, -z-1/2'

_cell_length_a                   13.2190(4)
_cell_length_b                   13.2190(4)
_cell_length_c                   20.9750(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3665.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4184
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.757
_exptl_crystal_F_000             2000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    3.275
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.389
_exptl_absorpt_correction_T_max  0.721
_exptl_absorpt_process_details   'Scalepak (Otwinowski, Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa-CCD'
_diffrn_measurement_method       'area detector ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7994
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.179
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4194
_reflns_number_gt                2960
_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       KappaCCD
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0512P)²+15.2107P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4194
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.1522
_refine_ls_wR_factor_gt          0.1358
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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
C1 C 0.5107(5) 0.1821(5) 0.0582(3) 0.0502(16) Uani 1 1 d . . . . .
H1A H 0.486158 0.152628 0.017704 0.060 Uiso 1 1 calc R U . . .
H1B H 0.498397 0.255941 0.056424 0.060 Uiso 1 1 calc R U . . .
C2 C 0.6231(6) 0.1644(5) 0.0629(3) 0.0586(19) Uani 1 1 d . . . . .
H2A H 0.649081 0.196248 0.101808 0.088 Uiso 1 1 calc R U . . .
H2B H 0.656729 0.193831 0.025679 0.088 Uiso 1 1 calc R U . . .
H2C H 0.636477 0.091496 0.064394 0.088 Uiso 1 1 calc R U . . .
C3 C 0.4886(5) -0.0840(4) 0.1058(2) 0.0402(13) Uani 1 1 d . . . . .
H3A H 0.499092 -0.043708 0.066599 0.048 Uiso 1 1 calc R U . . .
H3B H 0.439993 -0.138818 0.096048 0.048 Uiso 1 1 calc R U . . .
C4 C 0.5868(5) -0.1285(5) 0.1270(3) 0.0448(14) Uani 1 1 d . . . . .
H4A H 0.635402 -0.073301 0.135885 0.054 Uiso 1 1 calc R U . . .
H4B H 0.614994 -0.170597 0.092265 0.054 Uiso 1 1 calc R U . . .
C5 C 0.5743(5) -0.1921(5) 0.1857(3) 0.0454(14) Uani 1 1 d . . . . .
H5A H 0.558375 -0.262627 0.173347 0.054 Uiso 1 1 calc R U . . .
H5B H 0.638324 -0.192633 0.210223 0.054 Uiso 1 1 calc R U . . .
C6 C 0.4815(5) -0.2072(5) 0.2853(3) 0.0473(15) Uani 1 1 d . . . . .
H6A H 0.542613 -0.196786 0.311771 0.057 Uiso 1 1 calc R U . . .
H6B H 0.475941 -0.280408 0.275886 0.057 Uiso 1 1 calc R U . . .
C7 C 0.3895(5) -0.1734(5) 0.3219(3) 0.0485(15) Uani 1 1 d . . . . .
H7A H 0.327231 -0.197612 0.300536 0.058 Uiso 1 1 calc R U . . .
H7B H 0.391048 -0.201556 0.365658 0.058 Uiso 1 1 calc R U . . .
C8 C 0.3902(5) -0.0610(5) 0.3243(3) 0.0473(15) Uani 1 1 d . . . . .
H8A H 0.330901 -0.036936 0.348833 0.057 Uiso 1 1 calc R U . . .
H8B H 0.452053 -0.037646 0.346542 0.057 Uiso 1 1 calc R U . . .
C9 C 0.4426(4) -0.0619(4) 0.2145(2) 0.0378(12) Uani 1 1 d . . . . .
C10 C 0.1446(5) -0.0594(5) 0.1989(3) 0.0504(16) Uani 1 1 d . . . . .
H10A H 0.070317 -0.049806 0.197307 0.060 Uiso 1 1 calc R U . . .
H10B H 0.164431 -0.069461 0.243939 0.060 Uiso 1 1 calc R U . . .
C11 C 0.1733(5) -0.1504(5) 0.1606(3) 0.0545(17) Uani 1 1 d . . . . .
H11A H 0.141468 -0.211766 0.178743 0.065 Uiso 1 1 calc R U . . .
H11B H 0.247649 -0.159641 0.161222 0.065 Uiso 1 1 calc R U . . .
C12 C 0.1372(6) -0.1341(5) 0.0928(3) 0.0565(18) Uani 1 1 d . . . . .
H12A H 0.166803 -0.186424 0.064655 0.068 Uiso 1 1 calc R U . . .
H12B H 0.062607 -0.140779 0.091112 0.068 Uiso 1 1 calc R U . . .
C13 C 0.1456(5) -0.0202(5) 0.0037(3) 0.0521(16) Uani 1 1 d . . . . .
H13A H 0.073140 -0.034014 -0.004612 0.063 Uiso 1 1 calc R U . . .
H13B H 0.185989 -0.068831 -0.021594 0.063 Uiso 1 1 calc R U . . .
C14 C 0.1704(5) 0.0865(5) -0.0176(3) 0.0521(16) Uani 1 1 d . . . . .
H14A H 0.115305 0.133520 -0.005595 0.062 Uiso 1 1 calc R U . . .
H14B H 0.179498 0.089063 -0.064408 0.062 Uiso 1 1 calc R U . . .
C15 C 0.2694(5) 0.1157(5) 0.0165(2) 0.0441(15) Uani 1 1 d . . . . .
H15A H 0.322492 0.065073 0.007218 0.053 Uiso 1 1 calc R U . . .
H15B H 0.293035 0.182498 0.001212 0.053 Uiso 1 1 calc R U . . .
C16 C 0.2037(5) 0.0379(4) 0.1104(3) 0.0410(13) Uani 1 1 d . . . . .
O1 O 0.3605(3) 0.2057(3) 0.19412(15) 0.0370(9) Uani 1 1 d . . . . .
N1 N 0.4479(4) -0.0196(4) 0.1559(2) 0.0392(11) Uani 1 1 d . . . . .
N2 N 0.4922(4) -0.1514(4) 0.2257(2) 0.0393(11) Uani 1 1 d . . . . .
N3 N 0.3874(4) -0.0176(4) 0.2597(2) 0.0416(11) Uani 1 1 d . . . . .
N4 N 0.1950(4) 0.0301(4) 0.1734(2) 0.0412(11) Uani 1 1 d . . . . .
N5 N 0.1663(4) -0.0348(4) 0.0704(2) 0.0467(12) Uani 1 1 d . . . . .
N6 N 0.2502(4) 0.1198(4) 0.0857(2) 0.0426(12) Uani 1 1 d . . . . .
ZN1 Zn 0.43001(5) 0.12455(5) 0.12938(3) 0.0398(2) Uani 1 1 d . . . . .
ZN2 Zn 0.29266(5) 0.09143(5) 0.23802(3) 0.0379(2) Uani 1 1 d . . . . .
ZN3 Zn 0.250000 0.250000 0.13661(4) 0.0376(2) Uani 1 2 d S T P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.507(10) . ?
C1 ZN1 1.986(6) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 N1 1.455(7) . ?
C3 C4 1.493(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.500(8) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N2 1.473(7) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N2 1.459(7) . ?
C6 C7 1.507(9) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.487(9) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N3 1.471(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N3 1.333(7) . ?
C9 N1 1.352(6) . ?
C9 N2 1.372(7) . ?
C10 N4 1.458(7) . ?
C10 C11 1.496(9) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.515(9) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 N5 1.446(8) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 N5 1.439(7) . ?
C13 C14 1.515(9) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.540(9) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 N6 1.473(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 N4 1.331(7) . ?
C16 N6 1.349(7) . ?
C16 N5 1.369(7) . ?
O1 ZN2 1.937(3) 8_656 ?
O1 ZN1 1.959(3) . ?
O1 ZN3 1.983(4) . ?
O1 ZN2 1.983(4) . ?
N1 ZN1 2.000(5) . ?
N3 ZN2 1.963(5) . ?
N4 ZN2 2.040(5) . ?
N6 ZN3 2.026(5) . ?
ZN1 ZN3 2.9044(7) . ?
ZN1 ZN2 2.9463(9) . ?
ZN2 O1 1.937(3) 7_566 ?
ZN2 ZN3 3.0392(8) . ?
ZN2 ZN2 3.1106(10) 8_656 ?
ZN2 ZN2 3.1106(10) 7_566 ?
ZN3 O1 1.983(4) 2 ?
ZN3 N6 2.026(5) 2 ?
ZN3 ZN1 2.9044(7) 2 ?
ZN3 ZN2 3.0392(8) 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
C2 C1 ZN1 114.9(4) . . ?
C2 C1 H1A 108.6 . . ?
ZN1 C1 H1A 108.6 . . ?
C2 C1 H1B 108.6 . . ?
ZN1 C1 H1B 108.6 . . ?
H1A C1 H1B 107.5 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C4 109.7(4) . . ?
N1 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
N1 C3 H3B 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C3 C4 C5 111.7(5) . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
N2 C5 C4 110.0(5) . . ?
N2 C5 H5A 109.7 . . ?
C4 C5 H5A 109.7 . . ?
N2 C5 H5B 109.7 . . ?
C4 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
N2 C6 C7 111.4(5) . . ?
N2 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
N2 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 C6 107.9(5) . . ?
C8 C7 H7A 110.1 . . ?
C6 C7 H7A 110.1 . . ?
C8 C7 H7B 110.1 . . ?
C6 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
N3 C8 C7 111.0(5) . . ?
N3 C8 H8A 109.4 . . ?
C7 C8 H8A 109.4 . . ?
N3 C8 H8B 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
N3 C9 N1 119.6(5) . . ?
N3 C9 N2 121.3(5) . . ?
N1 C9 N2 119.1(5) . . ?
N4 C10 C11 109.9(5) . . ?
N4 C10 H10A 109.7 . . ?
C11 C10 H10A 109.7 . . ?
N4 C10 H10B 109.7 . . ?
C11 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
C10 C11 C12 108.0(6) . . ?
C10 C11 H11A 110.1 . . ?
C12 C11 H11A 110.1 . . ?
C10 C11 H11B 110.1 . . ?
C12 C11 H11B 110.1 . . ?
H11A C11 H11B 108.4 . . ?
N5 C12 C11 110.5(5) . . ?
N5 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
N5 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
N5 C13 C14 111.7(5) . . ?
N5 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
N5 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
C13 C14 C15 106.3(5) . . ?
C13 C14 H14A 110.5 . . ?
C15 C14 H14A 110.5 . . ?
C13 C14 H14B 110.5 . . ?
C15 C14 H14B 110.5 . . ?
H14A C14 H14B 108.7 . . ?
N6 C15 C14 108.7(5) . . ?
N6 C15 H15A 110.0 . . ?
C14 C15 H15A 110.0 . . ?
N6 C15 H15B 110.0 . . ?
C14 C15 H15B 110.0 . . ?
H15A C15 H15B 108.3 . . ?
N4 C16 N6 119.0(5) . . ?
N4 C16 N5 121.6(5) . . ?
N6 C16 N5 119.5(5) . . ?
ZN2 O1 ZN1 132.9(2) 8_656 . ?
ZN2 O1 ZN3 120.90(19) 8_656 . ?
ZN1 O1 ZN3 94.91(14) . . ?
ZN2 O1 ZN2 105.02(15) 8_656 . ?
ZN1 O1 ZN2 96.71(16) . . ?
ZN3 O1 ZN2 100.06(17) . . ?
C9 N1 C3 115.7(5) . . ?
C9 N1 ZN1 129.9(4) . . ?
C3 N1 ZN1 113.6(3) . . ?
C9 N2 C6 122.4(5) . . ?
C9 N2 C5 124.8(5) . . ?
C6 N2 C5 112.0(5) . . ?
C9 N3 C8 118.1(5) . . ?
C9 N3 ZN2 120.5(4) . . ?
C8 N3 ZN2 121.0(4) . . ?
C16 N4 C10 117.8(5) . . ?
C16 N4 ZN2 125.0(4) . . ?
C10 N4 ZN2 111.6(4) . . ?
C16 N5 C13 124.8(5) . . ?
C16 N5 C12 122.3(5) . . ?
C13 N5 C12 112.8(5) . . ?
C16 N6 C15 115.3(5) . . ?
C16 N6 ZN3 118.6(4) . . ?
C15 N6 ZN3 123.4(4) . . ?
O1 ZN1 C1 124.3(2) . . ?
O1 ZN1 N1 112.60(17) . . ?
C1 ZN1 N1 120.7(2) . . ?
O1 ZN1 ZN3 42.85(11) . . ?
C1 ZN1 ZN3 105.1(2) . . ?
N1 ZN1 ZN3 128.79(14) . . ?
O1 ZN1 ZN2 41.95(11) . . ?
C1 ZN1 ZN2 165.7(2) . . ?
N1 ZN1 ZN2 73.49(13) . . ?
ZN3 ZN1 ZN2 62.59(2) . . ?
O1 ZN2 N3 116.69(16) 7_566 . ?
O1 ZN2 O1 111.1(2) 7_566 . ?
N3 ZN2 O1 112.25(18) . . ?
O1 ZN2 N4 104.04(18) 7_566 . ?
N3 ZN2 N4 105.4(2) . . ?
O1 ZN2 N4 106.30(16) . . ?
O1 ZN2 ZN1 152.29(12) 7_566 . ?
N3 ZN2 ZN1 84.00(13) . . ?
O1 ZN2 ZN1 41.34(10) . . ?
N4 ZN2 ZN1 86.31(13) . . ?
O1 ZN2 ZN3 100.24(11) 7_566 . ?
N3 ZN2 ZN3 141.93(13) . . ?
O1 ZN2 ZN3 39.97(11) . . ?
N4 ZN2 ZN3 72.06(13) . . ?
ZN1 ZN2 ZN3 58.031(19) . . ?
O1 ZN2 ZN2 83.86(11) 7_566 8_656 ?
N3 ZN2 ZN2 106.04(16) . 8_656 ?
O1 ZN2 ZN2 36.97(9) . 8_656 ?
N4 ZN2 ZN2 139.39(13) . 8_656 ?
ZN1 ZN2 ZN2 72.20(3) . 8_656 ?
ZN3 ZN2 ZN2 67.334(16) . 8_656 ?
O1 ZN2 ZN2 38.01(11) 7_566 7_566 ?
N3 ZN2 ZN2 150.43(13) . 7_566 ?
O1 ZN2 ZN2 94.96(11) . 7_566 ?
N4 ZN2 ZN2 76.21(15) . 7_566 ?
ZN1 ZN2 ZN2 125.36(3) . 7_566 ?
ZN3 ZN2 ZN2 67.334(16) . 7_566 ?
ZN2 ZN2 ZN2 88.505(7) 8_656 7_566 ?
O1 ZN3 O1 105.05(19) . 2 ?
O1 ZN3 N6 93.97(18) . . ?
O1 ZN3 N6 124.95(18) 2 . ?
O1 ZN3 N6 124.95(18) . 2 ?
O1 ZN3 N6 93.97(18) 2 2 ?
N6 ZN3 N6 116.3(2) . 2 ?
O1 ZN3 ZN1 42.23(10) . . ?
O1 ZN3 ZN1 143.50(10) 2 . ?
N6 ZN3 ZN1 59.10(15) . . ?
N6 ZN3 ZN1 117.28(15) 2 . ?
O1 ZN3 ZN1 143.50(10) . 2 ?
O1 ZN3 ZN1 42.23(10) 2 2 ?
N6 ZN3 ZN1 117.29(15) . 2 ?
N6 ZN3 ZN1 59.10(15) 2 2 ?
ZN1 ZN3 ZN1 174.02(4) . 2 ?
O1 ZN3 ZN2 85.10(10) . 2 ?
O1 ZN3 ZN2 39.98(11) 2 2 ?
N6 ZN3 ZN2 162.82(13) . 2 ?
N6 ZN3 ZN2 77.48(13) 2 2 ?
ZN1 ZN3 ZN2 125.62(3) . 2 ?
ZN1 ZN3 ZN2 59.381(18) 2 2 ?
O1 ZN3 ZN2 39.98(11) . . ?
O1 ZN3 ZN2 85.10(10) 2 . ?
N6 ZN3 ZN2 77.48(13) . . ?
N6 ZN3 ZN2 162.82(13) 2 . ?
ZN1 ZN3 ZN2 59.382(18) . . ?
ZN1 ZN3 ZN2 125.62(3) 2 . ?
ZN2 ZN3 ZN2 91.16(3) 2 . ?

_refine_diff_density_max         0.863
_refine_diff_density_min         -0.645
_refine_diff_density_rms         0.118

