# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1821930'
_audit_update_record             
;
2018-03-02 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H10 N5 O8 Zn2'
_chemical_formula_weight         603.09

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      orthorhombic
_space_group_IT_number           69
_space_group_name_H-M_alt        'F m m m'
_space_group_name_Hall           '-F 2 2'

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

_cell_length_a                   28.34(3)
_cell_length_b                   34.85(3)
_cell_length_c                   17.761(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     17538(30)
_cell_formula_units_Z            16
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5679
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      28.17

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.914
_exptl_crystal_F_000             4816
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    1.126
_shelx_estimated_absorpt_T_min   0.790
_shelx_estimated_absorpt_T_max   0.823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38800
_diffrn_reflns_av_unetI/netI     0.0796
_diffrn_reflns_av_R_equivalents  0.1117
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.474
_diffrn_reflns_theta_max         28.267
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5751
_reflns_number_gt                4251
_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.
 
 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.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0746P)²+245.1236P] 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         5751
_refine_ls_number_parameters     186
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1146
_refine_ls_R_factor_gt           0.0899
_refine_ls_wR_factor_ref         0.2010
_refine_ls_wR_factor_gt          0.1905
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.089
_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 0.27787(19) 0.60928(16) 0.0653(2) 0.0382(13) Uani 1 1 d . . . . .
H1 H 0.2620 0.6053 0.1105 0.046 Uiso 1 1 calc R U . . .
C2 C 0.32384(19) 0.62181(16) 0.0683(2) 0.0367(13) Uani 1 1 d . . . . .
C3 C 0.3478(3) 0.6286(2) 0.0000 0.042(2) Uani 1 2 d S T P . .
H3 H 0.3788 0.6373 0.0000 0.050 Uiso 1 2 calc R U P . .
C4 C 0.34605(19) 0.62987(16) 0.1432(2) 0.0357(12) Uani 1 1 d . U . . .
C5 C 0.33129(19) 0.61055(17) 0.2078(2) 0.0390(14) Uani 1 1 d . . . . .
H5 H 0.3088 0.5912 0.2037 0.047 Uiso 1 1 calc R U . . .
C6 C 0.34972(18) 0.61971(16) 0.2786(2) 0.0336(12) Uani 1 1 d . . . . .
C7 C 0.38353(18) 0.64802(16) 0.2855(2) 0.0351(12) Uani 1 1 d . . . . .
H7 H 0.3957 0.6542 0.3326 0.042 Uiso 1 1 calc R U . . .
C8 C 0.39957(18) 0.66751(15) 0.2210(3) 0.0333(12) Uani 1 1 d . . . . .
C9 C 0.38066(19) 0.65848(16) 0.1505(2) 0.0383(13) Uani 1 1 d . . . . .
H9 H 0.3911 0.6716 0.1080 0.046 Uiso 1 1 calc R U . . .
C10 C 0.43619(17) 0.69857(16) 0.2281(3) 0.0333(12) Uani 1 1 d . . . . .
C11 C 0.33099(18) 0.59868(17) 0.3475(2) 0.0339(12) Uani 1 1 d . . . . .
C13 C 0.5000 0.7455(3) 0.5000 0.039(3) Uani 1 4 d S T P . .
H13 H 0.5000 0.7722 0.5000 0.047 Uiso 1 4 calc R U P . .
C14 C 0.3109(9) 0.5000 0.5000 0.115(8) Uani 1 4 d S T P . .
H14 H 0.2781 0.5000 0.5000 0.139 Uiso 1 4 calc R U P . .
N1 N 0.2544(2) 0.60244(19) 0.0000 0.0361(15) Uani 1 2 d S T P . .
N2 N 0.3311(3) 0.5316(2) 0.5000 0.0490(18) Uani 1 2 d S T P . .
N3 N 0.3692(5) 0.5196(4) 0.5470(9) 0.096(5) Uani 0.5 1 d . U P . .
N4 N 0.5000 0.72698(17) 0.4384(3) 0.0262(12) Uani 1 2 d S TU P . .
N5 N 0.5000 0.6920(4) 0.4629(6) 0.151(6) Uani 1 2 d S T P . .
O1 O 0.45028(15) 0.71444(12) 0.1689(2) 0.0467(10) Uani 1 1 d . . . . .
O2 O 0.44984(15) 0.70649(12) 0.2935(2) 0.0511(11) Uani 1 1 d . . . . .
O3 O 0.30368(14) 0.57134(12) 0.33863(19) 0.0432(10) Uani 1 1 d . . . . .
O4 O 0.34357(14) 0.61234(11) 0.41189(17) 0.0404(10) Uani 1 1 d . . . . .
Zn1 Zn 0.5000 0.74334(2) 0.33214(3) 0.0197(2) Uani 1 2 d S T P . .
Zn2 Zn 0.31565(3) 0.58623(2) 0.5000 0.0264(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 N1 1.358(5) . ?
C1 C2 1.375(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.409(6) . ?
C2 C4 1.499(6) . ?
C3 C2 1.409(6) 18 ?
C3 H3 0.9300 . ?
C4 C5 1.394(6) . ?
C4 C9 1.405(7) . ?
C5 C6 1.399(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.381(7) . ?
C6 C11 1.522(6) . ?
C7 C8 1.407(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.397(6) . ?
C8 C10 1.505(7) . ?
C9 H9 0.9300 . ?
C10 O1 1.253(6) . ?
C10 O2 1.255(6) . ?
C11 O3 1.238(6) . ?
C11 O4 1.289(6) . ?
C13 N4 1.272(8) 18_556 ?
C13 N4 1.272(8) . ?
C13 H13 0.9300 . ?
C14 N2 1.241(13) 19_565 ?
C14 N2 1.241(13) . ?
C14 H14 0.9300 . ?
N1 C1 1.358(5) 18 ?
N1 Zn2 2.064(6) 11 ?
N2 N3 1.426(15) . ?
N2 N3 1.426(15) 18_556 ?
N2 Zn2 1.954(8) . ?
N3 N3 1.37(3) 19_565 ?
N3 N3 1.67(3) 18_556 ?
N4 N5 1.294(15) . ?
N4 Zn1 1.971(5) . ?
N5 N5 1.32(2) 18_556 ?
O1 Zn1 2.037(4) 21_665 ?
O2 Zn1 2.035(4) . ?
O4 Zn2 1.976(3) . ?
Zn1 O2 2.035(4) 20_655 ?
Zn1 O1 2.037(4) 21_665 ?
Zn1 O1 2.037(4) 8_565 ?
Zn1 Zn1 2.954(3) 21_665 ?
Zn2 O4 1.975(3) 18_556 ?
Zn2 N1 2.064(6) 11 ?

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
N1 C1 C2 123.5(4) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C1 C2 C3 118.5(5) . . ?
C1 C2 C4 119.4(4) . . ?
C3 C2 C4 122.1(5) . . ?
C2 C3 C2 118.7(7) . 18 ?
C2 C3 H3 120.6 . . ?
C2 C3 H3 120.6 18 . ?
C5 C4 C9 118.4(4) . . ?
C5 C4 C2 120.9(4) . . ?
C9 C4 C2 120.6(4) . . ?
C4 C5 C6 121.2(5) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C7 C6 C5 120.1(4) . . ?
C7 C6 C11 121.0(4) . . ?
C5 C6 C11 118.9(5) . . ?
C6 C7 C8 119.8(4) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C9 C8 C7 119.8(4) . . ?
C9 C8 C10 120.1(4) . . ?
C7 C8 C10 120.2(4) . . ?
C8 C9 C4 120.7(4) . . ?
C8 C9 H9 119.6 . . ?
C4 C9 H9 119.6 . . ?
O1 C10 O2 125.5(5) . . ?
O1 C10 C8 117.9(4) . . ?
O2 C10 C8 116.6(4) . . ?
O3 C11 O4 124.7(4) . . ?
O3 C11 C6 119.1(4) . . ?
O4 C11 C6 116.1(5) . . ?
N4 C13 N4 118.8(10) 18_556 . ?
N4 C13 H13 120.6 18_556 . ?
N4 C13 H13 120.6 . . ?
N2 C14 N2 125(2) 19_565 . ?
N2 C14 H14 117.5 19_565 . ?
N2 C14 H14 117.5 . . ?
C1 N1 C1 117.4(6) 18 . ?
C1 N1 Zn2 121.2(3) 18 11 ?
C1 N1 Zn2 121.2(3) . 11 ?
C14 N2 N3 95.1(11) . . ?
C14 N2 N3 95.1(11) . 18_556 ?
N3 N2 N3 71.7(13) . 18_556 ?
C14 N2 Zn2 139.5(12) . . ?
N3 N2 Zn2 117.1(7) . . ?
N3 N2 Zn2 117.1(7) 18_556 . ?
N3 N3 N2 107.1(6) 19_565 . ?
N3 N3 N3 90.003(3) 19_565 18_556 ?
N2 N3 N3 54.2(7) . 18_556 ?
C13 N4 N5 100.9(7) . . ?
C13 N4 Zn1 132.6(6) . . ?
N5 N4 Zn1 126.5(6) . . ?
N4 N5 N5 109.7(5) . 18_556 ?
C10 O1 Zn1 123.1(3) . 21_665 ?
C10 O2 Zn1 131.8(4) . . ?
C11 O4 Zn2 115.0(3) . . ?
N4 Zn1 O2 98.07(17) . . ?
N4 Zn1 O2 98.07(17) . 20_655 ?
O2 Zn1 O2 88.6(3) . 20_655 ?
N4 Zn1 O1 102.56(16) . 21_665 ?
O2 Zn1 O1 159.37(15) . 21_665 ?
O2 Zn1 O1 88.3(2) 20_655 21_665 ?
N4 Zn1 O1 102.56(16) . 8_565 ?
O2 Zn1 O1 88.3(2) . 8_565 ?
O2 Zn1 O1 159.37(15) 20_655 8_565 ?
O1 Zn1 O1 87.5(3) 21_665 8_565 ?
N4 Zn1 Zn1 172.22(18) . 21_665 ?
O2 Zn1 Zn1 76.47(11) . 21_665 ?
O2 Zn1 Zn1 76.47(11) 20_655 21_665 ?
O1 Zn1 Zn1 82.98(10) 21_665 21_665 ?
O1 Zn1 Zn1 82.98(10) 8_565 21_665 ?
N2 Zn2 O4 111.03(18) . 18_556 ?
N2 Zn2 O4 111.03(18) . . ?
O4 Zn2 O4 104.8(2) 18_556 . ?
N2 Zn2 N1 118.9(3) . 11 ?
O4 Zn2 N1 105.02(17) 18_556 11 ?
O4 Zn2 N1 105.02(17) . 11 ?

_refine_diff_density_max         1.501
_refine_diff_density_min         -0.969
_refine_diff_density_rms         0.130



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

data_1-NH2
_database_code_depnum_ccdc_archive 'CCDC 1821931'
_audit_update_record             
;
2018-03-02 deposited with the CCDC.
2018-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H11 N6 O8 Zn2'
_chemical_formula_weight         618.11

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      orthorhombic
_space_group_IT_number           69
_space_group_name_H-M_alt        'F m m m'
_space_group_name_Hall           '-F 2 2'

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

_cell_length_a                   28.127(9)
_cell_length_b                   34.868(11)
_cell_length_c                   17.705(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     17364(9)
_cell_formula_units_Z            16
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6959
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      28.34

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.946
_exptl_crystal_F_000             4944
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    1.139
_shelx_estimated_absorpt_T_min   0.788
_shelx_estimated_absorpt_T_max   0.821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31433
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_av_R_equivalents  0.0873
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.479
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4113
_reflns_number_gt                3213
_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.
 
 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.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1111P)²+210.2163P] 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         4113
_refine_ls_number_parameters     198
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0764
_refine_ls_wR_factor_ref         0.2071
_refine_ls_wR_factor_gt          0.1942
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.113
_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
C1 C 0.2781(2) 0.60811(17) 0.5651(3) 0.0297(14) Uani 1 1 d . . . . .
H1 H 0.2622 0.6040 0.6104 0.036 Uiso 1 1 calc R U . . .
C2 C 0.3243(2) 0.62094(19) 0.5681(3) 0.0329(15) Uani 1 1 d . U . . .
C3 C 0.3478(3) 0.6269(3) 0.5000 0.038(2) Uani 1 2 d S T P . .
H3 H 0.3793 0.6350 0.5000 0.045 Uiso 1 2 calc R U P . .
C4 C 0.3463(2) 0.62947(19) 0.6431(3) 0.0356(16) Uani 1 1 d . . . . .
C5 C 0.3807(2) 0.65787(19) 0.6501(3) 0.0346(16) Uani 1 1 d . . . . .
H5 H 0.3913 0.6708 0.6073 0.041 Uiso 1 1 calc R U . . .
C6 C 0.3994(2) 0.66704(17) 0.7200(3) 0.0278(14) Uani 1 1 d . . . . .
C7 C 0.3834(2) 0.64790(18) 0.7846(3) 0.0305(14) Uani 1 1 d . . . . .
H7 H 0.3955 0.6544 0.8318 0.037 Uiso 1 1 calc R U . . .
C8 C 0.3500(2) 0.61953(18) 0.7781(3) 0.0274(14) Uani 1 1 d . . . . .
C9 C 0.3317(2) 0.61016(19) 0.7079(3) 0.0305(15) Uani 1 1 d . . . . .
H9 H 0.3094 0.5906 0.7040 0.037 Uiso 1 1 calc R U . . .
C10 C 0.3311(2) 0.59884(19) 0.8471(3) 0.0293(14) Uani 1 1 d . . . . .
C11 C 0.4361(2) 0.69822(17) 0.7275(3) 0.0272(13) Uani 1 1 d . . . . .
C12 C 0.5000 0.7490(3) 1.0000 0.031(3) Uani 1 4 d S T P . .
N6 N 0.5000 0.7886(4) 1.0000 0.085(5) Uani 1 4 d S TU P . .
H6A H 0.5000 0.8009 1.0421 0.102 Uiso 0.5 2 calc R U P . .
H6B H 0.5000 0.8009 0.9579 0.102 Uiso 0.5 2 calc R U P . .
C14 C 0.3152(6) 0.5000 1.0247(8) 0.029(4) Uani 0.5 2 d S T P . .
N7 N 0.2806(6) 0.5000 1.0817(9) 0.042(4) Uani 0.5 2 d S T P . .
H7A H 0.2509 0.5000 1.0699 0.051 Uiso 0.5 2 calc R U P . .
H7B H 0.2890 0.5000 1.1284 0.051 Uiso 0.5 2 calc R U P . .
N5 N 0.3658(4) 0.5177(3) 0.9425(7) 0.044(3) Uani 0.5 1 d . . P . .
N1 N 0.2546(2) 0.6011(2) 0.5000 0.0259(15) Uani 1 2 d S T P . .
N2 N 0.5000 0.72792(19) 0.9390(3) 0.0224(14) Uani 1 2 d S TU P . .
N3 N 0.5000 0.6910(2) 0.9635(4) 0.066(3) Uani 1 2 d S T P . .
N4 N 0.3334(2) 0.5313(2) 1.0000 0.0290(16) Uani 1 2 d S T P . .
O1 O 0.44986(16) 0.71401(14) 0.6678(2) 0.0439(13) Uani 1 1 d . . . . .
O2 O 0.44934(17) 0.70641(14) 0.7922(2) 0.0445(13) Uani 1 1 d . . . . .
O3 O 0.34397(14) 0.61231(12) 0.9113(2) 0.0296(9) Uani 1 1 d . U . . .
O4 O 0.30323(15) 0.57181(13) 0.8384(2) 0.0334(10) Uani 1 1 d . . . . .
Zn1 Zn 0.5000 0.74285(2) 0.83140(4) 0.0143(3) Uani 1 2 d S T P . .
Zn2 Zn 0.31651(3) 0.58638(3) 1.0000 0.0189(3) 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 N1 1.351(6) . ?
C1 C2 1.376(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.389(7) . ?
C2 C4 1.494(7) . ?
C3 C2 1.389(7) 18_556 ?
C3 H3 0.9300 . ?
C4 C5 1.391(8) . ?
C4 C9 1.392(8) . ?
C5 C6 1.383(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.397(8) . ?
C6 C11 1.506(8) . ?
C7 C8 1.370(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.384(7) . ?
C8 C10 1.514(7) . ?
C9 H9 0.9300 . ?
C10 O4 1.236(7) . ?
C10 O3 1.281(7) . ?
C11 O2 1.237(7) . ?
C11 O1 1.253(7) . ?
C12 N2 1.306(9) 18_557 ?
C12 N2 1.306(9) . ?
C12 N6 1.381(18) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
C14 C14 0.88(3) 18_557 ?
C14 N4 1.283(10) 19_565 ?
C14 N4 1.283(10) . ?
C14 N7 1.40(2) . ?
C14 N5 1.655(18) 18_557 ?
C14 N5 1.655(18) 4_567 ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N5 N5 1.24(2) 19_565 ?
N5 N4 1.445(12) . ?
N5 C14 1.655(18) 18_557 ?
N1 C1 1.351(6) 18_556 ?
N1 Zn2 2.064(7) 11_556 ?
N2 N3 1.358(10) . ?
N2 Zn1 1.975(6) . ?
N3 N3 1.293(15) 18_557 ?
N4 C14 1.283(10) 18_557 ?
N4 N5 1.445(12) 18_557 ?
N4 Zn2 1.978(7) . ?
O1 Zn1 2.062(4) 21_666 ?
O2 Zn1 2.032(4) . ?
O3 Zn2 1.970(4) . ?
Zn1 O2 2.032(4) 20_655 ?
Zn1 O1 2.062(4) 21_666 ?
Zn1 O1 2.062(4) 8_566 ?
Zn1 Zn1 2.9251(17) 21_666 ?
Zn2 O3 1.970(4) 18_557 ?
Zn2 N1 2.064(7) 11_556 ?

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
N1 C1 C2 123.7(5) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C1 C2 C3 117.6(5) . . ?
C1 C2 C4 119.3(5) . . ?
C3 C2 C4 123.1(6) . . ?
C2 C3 C2 120.4(8) . 18_556 ?
C2 C3 H3 119.8 . . ?
C2 C3 H3 119.8 18_556 . ?
C5 C4 C9 118.4(5) . . ?
C5 C4 C2 120.5(5) . . ?
C9 C4 C2 121.0(5) . . ?
C6 C5 C4 120.6(5) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 120.0(5) . . ?
C5 C6 C11 120.4(5) . . ?
C7 C6 C11 119.6(5) . . ?
C8 C7 C6 119.8(5) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 120.0(5) . . ?
C7 C8 C10 121.2(5) . . ?
C9 C8 C10 118.8(5) . . ?
C8 C9 C4 121.2(5) . . ?
C8 C9 H9 119.4 . . ?
C4 C9 H9 119.4 . . ?
O4 C10 O3 124.7(5) . . ?
O4 C10 C8 119.0(5) . . ?
O3 C10 C8 116.2(5) . . ?
O2 C11 O1 125.9(5) . . ?
O2 C11 C6 117.0(5) . . ?
O1 C11 C6 117.1(5) . . ?
N2 C12 N2 111.5(11) 18_557 . ?
N2 C12 N6 124.3(5) 18_557 . ?
N2 C12 N6 124.3(5) . . ?
C12 N6 H6A 120.0 . . ?
C12 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C14 C14 N4 70.1(6) 18_557 19_565 ?
C14 C14 N4 70.1(6) 18_557 . ?
N4 C14 N4 116.7(13) 19_565 . ?
C14 C14 N7 136.0(10) 18_557 . ?
N4 C14 N7 121.5(6) 19_565 . ?
N4 C14 N7 121.5(6) . . ?
C14 C14 N5 110.5(7) 18_557 18_557 ?
N4 C14 N5 95.5(11) 19_565 18_557 ?
N4 C14 N5 57.3(7) . 18_557 ?
N7 C14 N5 110.1(12) . 18_557 ?
C14 C14 N5 110.5(7) 18_557 4_567 ?
N4 C14 N5 57.3(7) 19_565 4_567 ?
N4 C14 N5 95.5(11) . 4_567 ?
N7 C14 N5 110.1(12) . 4_567 ?
N5 C14 N5 43.9(8) 18_557 4_567 ?
C14 N7 H7A 120.0 . . ?
C14 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
N5 N5 N4 109.2(5) 19_565 . ?
N5 N5 C14 68.1(4) 19_565 18_557 ?
N4 N5 C14 48.3(5) . 18_557 ?
C1 N1 C1 117.0(7) . 18_556 ?
C1 N1 Zn2 121.3(3) . 11_556 ?
C1 N1 Zn2 121.3(3) 18_556 11_556 ?
C12 N2 N3 105.7(7) . . ?
C12 N2 Zn1 130.5(6) . . ?
N3 N2 Zn1 123.9(5) . . ?
N3 N3 N2 108.6(4) 18_557 . ?
C14 N4 C14 39.9(13) 18_557 . ?
C14 N4 N5 102.2(9) 18_557 18_557 ?
C14 N4 N5 74.4(9) . 18_557 ?
C14 N4 N5 74.4(9) 18_557 . ?
C14 N4 N5 102.2(9) . . ?
N5 N4 N5 89.6(11) 18_557 . ?
C14 N4 Zn2 136.9(8) 18_557 . ?
C14 N4 Zn2 136.9(8) . . ?
N5 N4 Zn2 118.0(5) 18_557 . ?
N5 N4 Zn2 118.0(5) . . ?
C11 O1 Zn1 121.7(4) . 21_666 ?
C11 O2 Zn1 132.2(4) . . ?
C10 O3 Zn2 115.3(4) . . ?
N2 Zn1 O2 99.50(18) . . ?
N2 Zn1 O2 99.50(18) . 20_655 ?
O2 Zn1 O2 89.1(3) . 20_655 ?
N2 Zn1 O1 100.71(18) . 21_666 ?
O2 Zn1 O1 159.75(17) . 21_666 ?
O2 Zn1 O1 88.8(2) 20_655 21_666 ?
N2 Zn1 O1 100.71(18) . 8_566 ?
O2 Zn1 O1 88.8(2) . 8_566 ?
O2 Zn1 O1 159.76(17) 20_655 8_566 ?
O1 Zn1 O1 86.3(3) 21_666 8_566 ?
N2 Zn1 Zn1 174.5(2) . 21_666 ?
O2 Zn1 Zn1 76.68(12) . 21_666 ?
O2 Zn1 Zn1 76.68(12) 20_655 21_666 ?
O1 Zn1 Zn1 83.24(12) 21_666 21_666 ?
O1 Zn1 Zn1 83.24(12) 8_566 21_666 ?
O3 Zn2 O3 105.8(2) . 18_557 ?
O3 Zn2 N4 110.55(16) . . ?
O3 Zn2 N4 110.54(16) 18_557 . ?
O3 Zn2 N1 105.43(17) . 11_556 ?
O3 Zn2 N1 105.43(17) 18_557 11_556 ?
N4 Zn2 N1 118.3(3) . 11_556 ?

_refine_diff_density_max         1.096
_refine_diff_density_min         -0.941
_refine_diff_density_rms         0.154



