# 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_CP1
_database_code_depnum_ccdc_archive 'CCDC 1560856'
_audit_update_record             
;
2017-11-17 deposited with the CCDC.
2017-12-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H40 N4 O17 Zn2'
_chemical_formula_weight         931.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   7.9461(12)
_cell_length_b                   9.0703(13)
_cell_length_c                   14.198(2)
_cell_angle_alpha                77.108(2)
_cell_angle_beta                 75.211(2)
_cell_angle_gamma                68.670(2)
_cell_volume                     911.9(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5394
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      28.25
_exptl_crystal_description       Plates
_exptl_crystal_colour            'Pale Yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.696
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    1.403
_shelx_estimated_absorpt_T_min   0.695
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6964
_exptl_absorpt_correction_T_max  0.9594
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA_PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6481
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.499
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             3170
_reflns_number_gt                3054
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'BRUKER SMART'
_computing_cell_refinement       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0415P)²+0.7674P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3170
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_ref         0.0784
_refine_ls_wR_factor_gt          0.0778
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn -0.06595(3) 0.84313(3) 0.48646(2) 0.01864(10) Uani 1 1 d . . . . .
O9 O 0.4555(6) 0.9553(5) 0.1485(3) 0.0366(10) Uani 0.42 1 d . . P A 1
H9 H 0.373084 0.923362 0.187989 0.055 Uiso 0.42 1 d R U P A 1
O1 O 0.16794(19) 0.68128(17) 0.44487(10) 0.0184(3) Uani 1 1 d . . . . .
O2 O 0.2258(2) 0.82885(19) 0.29957(12) 0.0290(4) Uani 1 1 d . . . . .
O3 O 0.8141(2) 0.6167(2) 0.07389(13) 0.0389(5) Uani 1 1 d . . . . .
H3 H 0.881808 0.610518 0.017839 0.058 Uiso 0.5 1 d R U P . .
O4 O 0.9691(2) 0.3546(2) 0.09621(12) 0.0334(4) Uani 1 1 d . . . . .
H4 H 1.025982 0.353683 0.036766 0.050 Uiso 0.5 1 d R U P . .
O5 O 0.87593(19) 0.07026(17) 0.43446(11) 0.0187(3) Uani 1 1 d . . . . .
O6 O 0.5875(2) 0.11894(18) 0.51722(11) 0.0220(3) Uani 1 1 d . . . . .
O7 O -0.2250(2) 0.78858(18) 0.41234(11) 0.0233(3) Uani 1 1 d . . . . .
H7A H -0.216419 0.828999 0.351935 0.035 Uiso 1 1 d R U . . .
H7B H -0.337089 0.819919 0.441135 0.035 Uiso 1 1 d R U . . .
O8B O -0.0989(7) 0.9178(7) 0.2337(3) 0.0562(14) Uani 0.43 1 d . . P B 2
H8B H 0.010183 0.883570 0.242534 0.084 Uiso 0.43 1 d R U P B 2
O8A O -0.2243(6) 0.8919(5) 0.2156(3) 0.0529(10) Uani 0.57 1 d . . P B 1
H8A H -0.310101 0.893274 0.190618 0.079 Uiso 0.57 1 calc R U P B 1
N1 N -0.1590(2) 0.7366(2) 0.62154(13) 0.0202(4) Uani 1 1 d . . . . .
N2 N -0.4846(3) 0.5529(3) 0.95653(15) 0.0341(5) Uani 1 1 d . . . . .
O10 O 0.149(6) 0.882(5) 0.127(3) 0.086(11) Uiso 0.08 1 d . . P C 4
C1 C 0.4452(3) 0.5735(2) 0.33691(15) 0.0168(4) Uani 1 1 d . . . . .
C18 C 0.4273(7) 0.9749(6) 0.0390(4) 0.0773(15) Uani 0.84 1 d . . P A 1
H18A H 0.426094 0.871790 0.027190 0.093 Uiso 0.84 1 calc R U P A 1
H18B H 0.305536 1.055344 0.032365 0.093 Uiso 0.84 1 calc R U P A 1
C2 C 0.5622(3) 0.5886(3) 0.24672(16) 0.0201(4) Uani 1 1 d . . . . .
H2 H 0.533552 0.685376 0.202193 0.024 Uiso 1 1 calc R U . . .
C17B C -0.202(5) 1.079(4) 0.056(3) 0.094(10) Uiso 0.15 1 d . . P B .
C3 C 0.7214(3) 0.4624(3) 0.22135(15) 0.0201(4) Uani 1 1 d . . . . .
C20 C 0.317(14) 0.985(12) -0.050(7) 0.18(3) Uiso 0.1 1 d . . P C 4
C4 C 0.7676(3) 0.3214(3) 0.28730(15) 0.0185(4) Uani 1 1 d . . . . .
H4A H 0.876732 0.235756 0.270024 0.022 Uiso 1 1 calc R U . . .
C5 C 0.6530(3) 0.3072(2) 0.37825(15) 0.0156(4) Uani 1 1 d . . . . .
C6 C 0.4900(3) 0.4320(2) 0.40245(15) 0.0158(4) Uani 1 1 d . . . . .
H6 H 0.409557 0.420290 0.463795 0.019 Uiso 1 1 calc R U . . .
C7 C 0.2672(3) 0.7072(2) 0.36079(15) 0.0183(4) Uani 1 1 d . . . . .
C8 C 0.8432(3) 0.4781(3) 0.12410(16) 0.0237(5) Uani 1 1 d . . . . .
C9 C 0.7043(3) 0.1558(2) 0.44950(15) 0.0170(4) Uani 1 1 d . . . . .
C10 C -0.0691(3) 0.5811(3) 0.64876(17) 0.0227(5) Uani 1 1 d . . . . .
H10 H 0.034150 0.526057 0.604078 0.027 Uiso 1 1 calc R U . . .
C11 C -0.1214(3) 0.4989(3) 0.73893(17) 0.0256(5) Uani 1 1 d . . . . .
H11 H -0.053647 0.389695 0.756303 0.031 Uiso 1 1 calc R U . . .
C12 C -0.2743(3) 0.5771(3) 0.80433(17) 0.0268(5) Uani 1 1 d . . . . .
C13 C -0.3678(3) 0.7372(3) 0.77597(18) 0.0309(5) Uani 1 1 d . . . . .
H13 H -0.473545 0.793946 0.818636 0.037 Uiso 1 1 calc R U . . .
C14 C -0.3057(3) 0.8129(3) 0.68534(17) 0.0275(5) Uani 1 1 d . . . . .
H14 H -0.368698 0.923103 0.667207 0.033 Uiso 1 1 calc R U . . .
C15 C -0.3342(4) 0.4883(3) 0.89953(17) 0.0320(6) Uani 1 1 d . . . . .
H15 H -0.260306 0.381966 0.918812 0.038 Uiso 1 1 calc R U . . .
C16 C -0.0995(7) 0.9658(6) 0.1408(4) 0.0874(13) Uani 1 1 d . . . . .
C17A C 0.076(2) 1.001(2) 0.1414(12) 0.098(4) Uiso 0.35 1 d . . P B 1
C19 C 0.246(9) 0.968(7) 0.055(5) 0.107(17) Uiso 0.1 1 d . . P C 4


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 1.9493(14) . ?
Zn1 O5 1.9508(14) 1_465 ?
Zn1 N1 2.0316(18) . ?
Zn1 O7 2.0777(16) . ?
O9 C18 1.588(7) . ?
O9 H9 0.8400 . ?
O1 C7 1.277(3) . ?
O2 C7 1.239(3) . ?
O3 C8 1.271(3) . ?
O3 H3 0.8398 . ?
O4 C8 1.262(3) . ?
O4 H4 0.8499 . ?
O5 C9 1.290(3) . ?
O6 C9 1.235(3) . ?
O7 H7A 0.8501 . ?
O7 H7B 0.8500 . ?
O8B C16 1.295(7) . ?
O8B H8B 0.8401 . ?
O8A C16 1.479(6) . ?
O8A H8A 0.8400 . ?
N1 C14 1.346(3) . ?
N1 C10 1.347(3) . ?
N2 C15 1.279(3) . ?
N2 N2 1.411(4) 2_467 ?
O10 C19 1.39(7) . ?
C1 C2 1.389(3) . ?
C1 C6 1.394(3) . ?
C1 C7 1.509(3) . ?
C18 C18 1.508(11) 2_675 ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C2 C3 1.392(3) . ?
C2 H2 0.9500 . ?
C17B C20 1.28(10) 2_575 ?
C17B C16 1.58(4) . ?
C17B C19 1.87(7) 2_575 ?
C3 C4 1.395(3) . ?
C3 C8 1.481(3) . ?
C20 C19 1.44(11) . ?
C4 C5 1.387(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.399(3) . ?
C5 C9 1.503(3) . ?
C6 H6 0.9500 . ?
C10 C11 1.377(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.390(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(4) . ?
C12 C15 1.472(3) . ?
C13 C14 1.378(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17A 1.541(16) . ?

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
O1 Zn1 O5 123.84(6) . 1_465 ?
O1 Zn1 N1 102.03(7) . . ?
O5 Zn1 N1 129.17(7) 1_465 . ?
O1 Zn1 O7 97.95(6) . . ?
O5 Zn1 O7 97.98(6) 1_465 . ?
N1 Zn1 O7 95.89(7) . . ?
C18 O9 H9 109.5 . . ?
C7 O1 Zn1 119.81(13) . . ?
C8 O3 H3 109.6 . . ?
C8 O4 H4 121.4 . . ?
C9 O5 Zn1 116.46(13) . 1_645 ?
Zn1 O7 H7A 114.1 . . ?
Zn1 O7 H7B 109.2 . . ?
H7A O7 H7B 109.2 . . ?
C16 O8B H8B 109.1 . . ?
C16 O8A H8A 109.5 . . ?
C14 N1 C10 118.19(19) . . ?
C14 N1 Zn1 123.57(15) . . ?
C10 N1 Zn1 118.24(15) . . ?
C15 N2 N2 111.3(3) . 2_467 ?
C2 C1 C6 119.46(19) . . ?
C2 C1 C7 119.65(19) . . ?
C6 C1 C7 120.83(18) . . ?
C18 C18 O9 114.3(5) 2_675 . ?
C18 C18 H18A 108.7 2_675 . ?
O9 C18 H18A 108.7 . . ?
C18 C18 H18B 108.7 2_675 . ?
O9 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C1 C2 C3 120.24(19) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C20 C17B C16 105(5) 2_575 . ?
C20 C17B C19 50(5) 2_575 2_575 ?
C16 C17B C19 131(3) . 2_575 ?
C2 C3 C4 120.35(19) . . ?
C2 C3 C8 119.90(19) . . ?
C4 C3 C8 119.75(19) . . ?
C17B C20 C19 87(7) 2_575 . ?
C5 C4 C3 119.56(19) . . ?
C5 C4 H4A 120.2 . . ?
C3 C4 H4A 120.2 . . ?
C4 C5 C6 120.06(19) . . ?
C4 C5 C9 119.39(18) . . ?
C6 C5 C9 120.54(18) . . ?
C1 C6 C5 120.27(19) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
O2 C7 O1 125.20(19) . . ?
O2 C7 C1 119.81(19) . . ?
O1 C7 C1 114.97(18) . . ?
O4 C8 O3 124.0(2) . . ?
O4 C8 C3 118.6(2) . . ?
O3 C8 C3 117.4(2) . . ?
O6 C9 O5 123.57(19) . . ?
O6 C9 C5 121.09(18) . . ?
O5 C9 C5 115.34(17) . . ?
N1 C10 C11 122.4(2) . . ?
N1 C10 H10 118.8 . . ?
C11 C10 H10 118.8 . . ?
C10 C11 C12 119.4(2) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C13 C12 C11 118.2(2) . . ?
C13 C12 C15 122.3(2) . . ?
C11 C12 C15 119.6(2) . . ?
C14 C13 C12 119.4(2) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
N1 C14 C13 122.4(2) . . ?
N1 C14 H14 118.8 . . ?
C13 C14 H14 118.8 . . ?
N2 C15 C12 120.7(2) . . ?
N2 C15 H15 119.7 . . ?
C12 C15 H15 119.7 . . ?
O8A C16 C17A 134.3(7) . . ?
O8B C16 C17B 149.3(15) . . ?
O8A C16 C17B 110.6(14) . . ?
C17A C16 C17B 111.7(16) . . ?
O10 C19 C20 140(7) . . ?

_refine_diff_density_max         0.454
_refine_diff_density_min         -0.394
_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_cp2_sq
_database_code_depnum_ccdc_archive 'CCDC 1560857'
_audit_update_record             
;
2017-11-30 deposited with the CCDC.
2017-12-06 downloaded from the CCDC.
;

_audit_creation_date             2017-11-28
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C54 H44 N12 O18 Zn5, 11(C H4 O), 4(H2 O)'
_chemical_formula_sum            'C65 H96 N12 O33 Zn5'
_chemical_formula_weight         1900.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.3241(17)
_cell_length_b                   11.0585(18)
_cell_length_c                   19.221(3)
_cell_angle_alpha                85.079(3)
_cell_angle_beta                 83.258(3)
_cell_angle_gamma                64.713(3)
_cell_volume                     1968.9(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2644
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.38
_cell_measurement_theta_min      2.19
_shelx_estimated_absorpt_T_max   0.939
_shelx_estimated_absorpt_T_min   0.741
_exptl_absorpt_coefficient_mu    1.596
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.7437
_exptl_absorpt_correction_T_max  0.9397
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plates
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0996
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14187
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.038
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD DIFFARCTOMETER'
_diffrn_measurement_method       OMEGA-PHISCAN
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_number_gt                5337
_reflns_number_total             6892
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'BRUKER SMART'
_computing_cell_refinement       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS (Sheldrick, 2015)'
_refine_diff_density_max         1.518
_refine_diff_density_min         -1.932
_refine_diff_density_rms         0.162
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     450
_refine_ls_number_reflns         6892
_refine_ls_number_restraints     334
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0877
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0860P)²+12.6170P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1998
_refine_ls_wR_factor_ref         0.2101
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups, All O(H,H,H) groups
2. Restrained distances
 O1AA-C1AA
 1.4 with sigma of 0.02
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4. Others
 Fixed Sof: H7A(0.5) H7C(0.5) O1AA(0.5) H1AA(0.5) C1AA(0.5) H1AB(0.5)
 H1AC(0.5) H1AD(0.5)
5.a Riding coordinates:
 O8(H8), O9(H9), O1AA(H1AA), C1AA(H1AB,H1AC,H1AD), O10(H10A,H10B), O11(H11A,
 H11B)
5.b Rotating group:
 O7(H7A,H7B,H7C)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C24(H24), C25(H25),
  C26(H26), C27(H27)
5.d Idealised Me refined as rotating group:
 C0AA(H0AB,H0AC,H0AD)
5.e Idealised tetrahedral OH refined as rotating group:
 O0AA(H0AA)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.44599(9) 0.76706(8) 0.89351(5) 0.0106(2) Uani 1 1 d . U . . .
Zn2 Zn 0.77240(9) 0.49802(8) 0.91037(5) 0.0108(2) Uani 1 1 d . U . . .
Zn3 Zn 0.500000 0.500000 1.000000 0.0106(3) Uani 1 2 d S TU P . .
O1 O 0.5513(5) 0.8676(5) 0.9202(3) 0.0135(12) Uani 1 1 d . U . . .
O2 O 0.7552(6) 0.6844(5) 0.9235(3) 0.0189(13) Uani 1 1 d . U . . .
O3 O 0.6061(5) 1.2980(5) 0.9792(3) 0.0135(12) Uani 1 1 d . U . . .
O4 O 0.7996(6) 1.3049(5) 0.9153(3) 0.0135(12) Uani 1 1 d . U . . .
O5 O 1.2202(5) 0.7037(5) 0.8817(3) 0.0159(12) Uani 1 1 d . U . . .
O6 O 1.2362(5) 0.8876(5) 0.9054(3) 0.0136(12) Uani 1 1 d . U . . .
O7 O 0.9857(6) 0.4314(6) 0.9376(3) 0.0235(14) Uani 1 1 d . U . . .
H7A H 0.984855 0.458683 0.979103 0.035 Uiso 0.5 1 d GR . . . .
H7B H 1.032716 0.465082 0.907153 0.035 Uiso 1 1 d GR . . . .
H7C H 1.032685 0.345542 0.930084 0.035 Uiso 0.5 1 d GR . . . .
O8 O 0.5504(5) 0.5709(5) 0.9027(3) 0.0090(11) Uani 1 1 d . U . . .
H8 H 0.520983 0.547043 0.869046 0.013 Uiso 1 1 d R . . . .
O9 O 0.6938(5) 0.5062(5) 1.0244(3) 0.0130(12) Uani 1 1 d . U . . .
H9 H 0.732964 0.431003 1.046167 0.019 Uiso 1 1 d R . . . .
N1 N 0.4709(7) 0.8068(7) 0.7834(4) 0.0164(14) Uani 1 1 d . U . . .
N2 N 0.5015(11) 0.9958(9) 0.5371(4) 0.045(2) Uani 1 1 d . U . . .
N3 N 0.8204(7) 0.5036(6) 0.8011(4) 0.0176(15) Uani 1 1 d . U . . .
N4 N 0.8364(11) 0.6664(9) 0.5508(4) 0.049(3) Uani 1 1 d . U . . .
N5 N 0.8320(11) 0.6712(9) 0.4759(4) 0.049(3) Uani 1 1 d . U . . .
N6 N 0.8440(10) 0.8381(9) 0.2258(4) 0.041(2) Uani 1 1 d . U . . .
C1 C 0.6845(8) 0.8088(7) 0.9234(4) 0.0108(15) Uani 1 1 d . U . . .
C2 C 0.7690(8) 0.8910(7) 0.9237(4) 0.0095(15) Uani 1 1 d . U . . .
C3 C 0.7027(8) 1.0274(7) 0.9350(4) 0.0118(16) Uani 1 1 d . U . . .
H3 H 0.601422 1.071661 0.945278 0.014 Uiso 1 1 calc R . . . .
C4 C 0.7866(8) 1.0976(7) 0.9311(4) 0.0078(15) Uiso 1 1 d . U . . .
C5 C 0.9350(8) 1.0319(7) 0.9173(4) 0.0102(16) Uani 1 1 d . U . . .
H5 H 0.991386 1.081542 0.913841 0.012 Uiso 1 1 calc R . . . .
C6 C 1.0011(8) 0.8967(7) 0.9084(4) 0.0101(15) Uani 1 1 d . U . . .
C7 C 0.9189(8) 0.8248(8) 0.9119(4) 0.0113(16) Uani 1 1 d . U . . .
H7 H 0.964014 0.730785 0.906426 0.014 Uiso 1 1 calc R . . . .
C8 C 0.7243(8) 1.2464(7) 0.9420(4) 0.0105(16) Uiso 1 1 d . U . . .
C9 C 1.1628(8) 0.8229(8) 0.8974(4) 0.0124(16) Uani 1 1 d . U . . .
C10 C 0.4993(9) 0.9108(9) 0.7576(5) 0.0244(19) Uani 1 1 d . U . . .
H10 H 0.514665 0.964103 0.789139 0.029 Uiso 1 1 calc R . . . .
C11 C 0.5065(10) 0.9421(9) 0.6870(5) 0.031(2) Uani 1 1 d . U . . .
H11 H 0.525411 1.016793 0.670191 0.037 Uiso 1 1 calc R . . . .
C12 C 0.4859(11) 0.8631(10) 0.6397(5) 0.031(2) Uani 1 1 d . U . . .
C13 C 0.4600(10) 0.7566(9) 0.6669(5) 0.030(2) Uani 1 1 d . U . . .
H13 H 0.445443 0.700780 0.636618 0.036 Uiso 1 1 calc R . . . .
C14 C 0.4551(10) 0.7300(9) 0.7383(5) 0.025(2) Uani 1 1 d . U . . .
H14 H 0.439850 0.653896 0.756166 0.030 Uiso 1 1 calc R . . . .
C15 C 0.4906(11) 0.8920(10) 0.5644(5) 0.033(2) Uani 1 1 d . U . . .
H15 H 0.485183 0.830479 0.534528 0.040 Uiso 1 1 calc R . . . .
C16 C 0.8432(10) 0.6054(9) 0.7680(5) 0.028(2) Uani 1 1 d . U . . .
H16 H 0.855665 0.666463 0.795490 0.034 Uiso 1 1 calc R . . . .
C17 C 0.8497(11) 0.6262(10) 0.6965(5) 0.035(2) Uani 1 1 d . U . . .
H17 H 0.865713 0.700156 0.675555 0.042 Uiso 1 1 calc R . . . .
C18 C 0.8326(10) 0.5383(10) 0.6550(5) 0.029(2) Uani 1 1 d . U . . .
C19 C 0.8134(11) 0.4305(10) 0.6887(5) 0.035(2) Uani 1 1 d . U . . .
H19 H 0.803089 0.366990 0.662252 0.042 Uiso 1 1 calc R . . . .
C20 C 0.8092(10) 0.4156(9) 0.7608(5) 0.028(2) Uani 1 1 d . U . . .
H20 H 0.798021 0.339954 0.782851 0.034 Uiso 1 1 calc R . . . .
C21 C 0.8322(11) 0.5600(10) 0.5790(5) 0.039(3) Uani 1 1 d . U . . .
H21 H 0.828870 0.494915 0.550915 0.046 Uiso 1 1 calc R . . . .
C22 C 0.8413(12) 0.7759(11) 0.4479(5) 0.041(3) Uani 1 1 d . U . . .
H22 H 0.848702 0.838857 0.475959 0.049 Uiso 1 1 calc R . . . .
C23 C 0.8403(11) 0.7981(10) 0.3720(5) 0.035(2) Uani 1 1 d . U . . .
C24 C 0.8727(12) 0.8992(10) 0.3378(5) 0.038(2) Uani 1 1 d . U . . .
H24 H 0.893032 0.957597 0.363619 0.046 Uiso 1 1 calc R . . . .
C25 C 0.8749(12) 0.9131(11) 0.2656(5) 0.042(3) Uani 1 1 d . U . . .
H25 H 0.900240 0.980729 0.242865 0.051 Uiso 1 1 calc R . . . .
C26 C 0.8096(13) 0.7426(12) 0.2589(6) 0.047(3) Uani 1 1 d . U . . .
H26 H 0.785917 0.688775 0.231440 0.056 Uiso 1 1 calc R . . . .
C27 C 0.8066(12) 0.7176(11) 0.3309(6) 0.042(3) Uani 1 1 d . U . . .
H27 H 0.782468 0.648158 0.351902 0.050 Uiso 1 1 calc R . . . .
O1AA O 1.1303(15) 0.5389(14) 0.8221(8) 0.041(4) Uani 0.5 1 d D U . . .
H1AA H 1.157972 0.557003 0.857634 0.061 Uiso 0.5 1 d R . . . .
C1AA C 1.173(4) 0.605(3) 0.7598(11) 0.087(11) Uani 0.5 1 d D U . . .
H1AB H 1.163627 0.566131 0.717570 0.131 Uiso 0.5 1 d R . . . .
H1AC H 1.107067 0.700231 0.760010 0.131 Uiso 0.5 1 d R . . . .
H1AD H 1.271727 0.594231 0.760010 0.131 Uiso 0.5 1 d R . . . .
O0AA O 0.5005(14) 0.5965(12) 1.1966(5) 0.088(3) Uani 1 1 d . U . . .
H0AA H 0.564819 0.519466 1.204055 0.131 Uiso 1 1 calc GR . . . .
C0AA C 0.4819(13) 0.6760(13) 1.2525(6) 0.053(3) Uani 1 1 d . U . . .
H0AB H 0.491840 0.757728 1.234863 0.079 Uiso 1 1 calc GR . . . .
H0AC H 0.554976 0.626536 1.285084 0.079 Uiso 1 1 calc GR . . . .
H0AD H 0.385963 0.699716 1.276860 0.079 Uiso 1 1 calc GR . . . .
O10 O 0.8216(6) 0.8310(5) 0.0878(3) 0.0191(13) Uani 1 1 d . U . . .
H10A H 0.832507 0.842417 0.130621 0.029 Uiso 1 1 d R . . . .
H10B H 0.754687 0.802047 0.092161 0.029 Uiso 1 1 d R . . . .
O11 O 0.6320(7) 0.7220(6) 1.0899(4) 0.0355(17) Uani 1 1 d . U . . .
H11A H 0.568488 0.696056 1.111122 0.053 Uiso 1 1 d R . . . .
H11B H 0.705568 0.648156 1.078172 0.053 Uiso 1 1 d R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 1.986(5) . ?
Zn1 O6 1.997(5) 1_455 ?
Zn1 O8 1.970(5) . ?
Zn1 N1 2.133(7) . ?
Zn2 O2 2.027(5) . ?
Zn2 O4 2.027(5) 1_545 ?
Zn2 O7 2.118(5) . ?
Zn2 O8 2.099(5) . ?
Zn2 O9 2.242(5) . ?
Zn2 N3 2.102(7) . ?
Zn3 O3 2.075(5) 2_677 ?
Zn3 O3 2.075(5) 1_545 ?
Zn3 O8 2.062(5) . ?
Zn3 O8 2.062(5) 2_667 ?
Zn3 O9 2.138(5) 2_667 ?
Zn3 O9 2.138(5) . ?
O1 C1 1.252(9) . ?
O2 C1 1.252(9) . ?
O3 C8 1.263(9) . ?
O4 C8 1.251(9) . ?
O5 C9 1.240(9) . ?
O6 C9 1.274(9) . ?
N1 C10 1.345(11) . ?
N1 C14 1.332(11) . ?
N2 N2 1.426(16) 2_676 ?
N2 C15 1.264(12) . ?
N3 C16 1.341(11) . ?
N3 C20 1.345(11) . ?
N4 N5 1.443(12) . ?
N4 C21 1.268(13) . ?
N5 C22 1.271(13) . ?
N6 C25 1.329(14) . ?
N6 C26 1.342(14) . ?
C1 C2 1.505(10) . ?
C2 C3 1.390(10) . ?
C2 C7 1.401(10) . ?
C3 C4 1.380(10) . ?
C4 C5 1.391(10) . ?
C4 C8 1.512(10) . ?
C5 C6 1.369(10) . ?
C6 C7 1.382(11) . ?
C6 C9 1.510(10) . ?
C10 C11 1.373(13) . ?
C11 C12 1.405(14) . ?
C12 C13 1.365(13) . ?
C12 C15 1.456(13) . ?
C13 C14 1.379(13) . ?
C16 C17 1.373(13) . ?
C17 C18 1.387(14) . ?
C18 C19 1.386(14) . ?
C18 C21 1.459(13) . ?
C19 C20 1.378(13) . ?
C22 C23 1.458(14) . ?
C23 C24 1.391(14) . ?
C23 C27 1.410(15) . ?
C24 C25 1.382(14) . ?
C26 C27 1.386(15) . ?
O1AA C1AA 1.469(17) . ?
O0AA C0AA 1.391(14) . ?

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
O1 Zn1 O6 107.4(2) . 1_455 ?
O1 Zn1 N1 95.8(2) . . ?
O6 Zn1 N1 95.5(2) 1_455 . ?
O8 Zn1 O1 114.7(2) . . ?
O8 Zn1 O6 131.4(2) . 1_455 ?
O8 Zn1 N1 103.0(2) . . ?
O2 Zn2 O4 169.6(2) . 1_545 ?
O2 Zn2 O7 85.4(2) . . ?
O2 Zn2 O8 91.7(2) . . ?
O2 Zn2 O9 83.9(2) . . ?
O2 Zn2 N3 95.0(2) . . ?
O4 Zn2 O7 88.9(2) 1_545 . ?
O4 Zn2 O8 92.5(2) 1_545 . ?
O4 Zn2 O9 87.5(2) 1_545 . ?
O4 Zn2 N3 94.2(2) 1_545 . ?
O7 Zn2 O9 89.8(2) . . ?
O8 Zn2 O7 169.7(2) . . ?
O8 Zn2 O9 80.03(19) . . ?
O8 Zn2 N3 93.3(2) . . ?
N3 Zn2 O7 96.8(3) . . ?
N3 Zn2 O9 173.2(2) . . ?
O3 Zn3 Zn2 80.17(14) 2_677 2_667 ?
O3 Zn3 Zn2 99.83(14) 1_545 2_667 ?
O3 Zn3 O3 180.0(3) 2_677 1_545 ?
O3 Zn3 O9 91.9(2) 2_677 2_667 ?
O3 Zn3 O9 91.9(2) 1_545 . ?
O3 Zn3 O9 88.1(2) 1_545 2_667 ?
O3 Zn3 O9 88.1(2) 2_677 . ?
O8 Zn3 Zn2 137.97(14) . 2_667 ?
O8 Zn3 Zn2 42.03(14) 2_667 2_667 ?
O8 Zn3 O3 96.6(2) 2_667 2_677 ?
O8 Zn3 O3 96.6(2) . 1_545 ?
O8 Zn3 O3 83.4(2) . 2_677 ?
O8 Zn3 O3 83.4(2) 2_667 1_545 ?
O8 Zn3 O8 180.0 . 2_667 ?
O8 Zn3 O9 96.6(2) . 2_667 ?
O8 Zn3 O9 83.4(2) . . ?
O8 Zn3 O9 96.6(2) 2_667 . ?
O8 Zn3 O9 83.4(2) 2_667 2_667 ?
O9 Zn3 Zn2 133.94(15) . 2_667 ?
O9 Zn3 Zn2 46.06(15) 2_667 2_667 ?
O9 Zn3 O9 180.0(3) 2_667 . ?
C1 O1 Zn1 119.5(5) . . ?
C1 O2 Zn2 151.3(5) . . ?
C8 O3 Zn3 124.2(5) . 1_565 ?
C8 O4 Zn2 133.7(5) . 1_565 ?
C9 O6 Zn1 110.0(5) . 1_655 ?
Zn1 O8 Zn2 115.4(2) . . ?
Zn1 O8 Zn3 111.0(2) . . ?
Zn3 O8 Zn2 96.8(2) . . ?
Zn3 O9 Zn2 90.6(2) . . ?
C10 N1 Zn1 121.4(6) . . ?
C14 N1 Zn1 120.2(6) . . ?
C14 N1 C10 118.4(8) . . ?
C15 N2 N2 112.1(12) . 2_676 ?
C16 N3 Zn2 121.3(6) . . ?
C16 N3 C20 117.0(8) . . ?
C20 N3 Zn2 121.0(6) . . ?
C21 N4 N5 111.4(9) . . ?
C22 N5 N4 110.9(10) . . ?
C25 N6 C26 116.8(9) . . ?
O1 C1 O2 124.4(7) . . ?
O1 C1 C2 119.0(7) . . ?
O2 C1 C2 116.6(6) . . ?
C3 C2 C1 122.1(7) . . ?
C3 C2 C7 120.5(7) . . ?
C7 C2 C1 117.4(6) . . ?
C4 C3 C2 118.8(7) . . ?
C3 C4 C5 120.3(7) . . ?
C3 C4 C8 122.8(7) . . ?
C5 C4 C8 116.9(6) . . ?
C6 C5 C4 121.0(7) . . ?
C5 C6 C7 119.6(7) . . ?
C5 C6 C9 121.5(7) . . ?
C7 C6 C9 118.9(7) . . ?
C6 C7 C2 119.7(7) . . ?
O3 C8 C4 117.7(6) . . ?
O4 C8 O3 126.5(7) . . ?
O4 C8 C4 115.8(6) . . ?
O5 C9 O6 122.1(7) . . ?
O5 C9 C6 120.7(7) . . ?
O6 C9 C6 117.3(7) . . ?
N1 C10 C11 121.7(9) . . ?
C10 C11 C12 119.8(9) . . ?
C11 C12 C15 122.3(9) . . ?
C13 C12 C11 117.6(9) . . ?
C13 C12 C15 120.1(10) . . ?
C12 C13 C14 119.8(9) . . ?
N1 C14 C13 122.7(8) . . ?
N2 C15 C12 122.6(10) . . ?
N3 C16 C17 123.5(9) . . ?
C16 C17 C18 119.6(9) . . ?
C17 C18 C21 121.3(10) . . ?
C19 C18 C17 117.2(9) . . ?
C19 C18 C21 121.4(10) . . ?
C20 C19 C18 120.0(10) . . ?
N3 C20 C19 122.7(9) . . ?
N4 C21 C18 119.4(10) . . ?
N5 C22 C23 119.1(11) . . ?
C24 C23 C22 121.2(10) . . ?
C24 C23 C27 117.8(9) . . ?
C27 C23 C22 121.0(10) . . ?
C25 C24 C23 118.8(10) . . ?
N6 C25 C24 124.4(11) . . ?
N6 C26 C27 124.0(11) . . ?
C26 C27 C23 118.2(10) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
