# 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 1871006'
_audit_update_record             
;
2018-11-05 deposited with the CCDC.
2018-11-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H15 N3 O4 Zn'
_chemical_formula_weight         462.77

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/m


loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.000 0.000 0.000 188.5 32.0
2 0.500 0.500 0.000 188.5 32.0
_platon_squeeze_details          
;
;

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

_cell_length_a                   20.1904(17)
_cell_length_b                   10.0161(9)
_cell_length_c                   11.4086(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.609(9)
_cell_angle_gamma                90.00
_cell_volume                     2267.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1729
_cell_measurement_theta_min      3.6990
_cell_measurement_theta_max      30.7220

_exptl_crystal_description       colorless
_exptl_crystal_colour            block
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    1.115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89442
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4131
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.79
_diffrn_reflns_theta_max         25.20
_reflns_number_total             2172
_reflns_number_gt                1962
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1068P)²+16.0016P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2172
_refine_ls_number_parameters     178
_refine_ls_number_restraints     85
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0690
_refine_ls_wR_factor_ref         0.2002
_refine_ls_wR_factor_gt          0.1953
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_restrained_S_all      1.272
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.14164(4) 0.5000 0.32253(7) 0.0268(4) Uani 1 2 d S . .
O1 O 0.0677(3) 0.3545(5) 0.3114(4) 0.0577(14) Uani 1 1 d . . .
O2 O 0.1605(3) 0.2435(7) 0.3193(6) 0.0832(19) Uani 1 1 d U . .
N1 N -0.2506(3) 0.0000 0.3426(6) 0.0312(14) Uani 1 2 d S . .
N2 N 0.1388(4) 0.5000 0.1297(6) 0.0387(16) Uani 1 2 d SU . .
C13 C 0.0976(6) 0.4313(15) 0.0535(11) 0.048(3) Uani 0.50 1 d PU . .
C10 C 0.1827(7) 0.5923(15) -0.0338(12) 0.050(3) Uani 0.50 1 d PU . .
C12 C 0.0957(7) 0.4320(16) -0.0688(12) 0.051(3) Uani 0.50 1 d P . .
C2 C -0.1471(4) 0.1078(9) 0.3510(12) 0.093(3) Uani 1 1 d U . .
H2A H -0.1248 0.1892 0.3638 0.111 Uiso 1 1 calc R . .
C8 C 0.0995(3) 0.2482(8) 0.3166(5) 0.0490(18) Uani 1 1 d . . .
C5 C -0.0054(3) 0.1194(5) 0.3291(5) 0.0299(11) Uani 1 1 d . . .
H5A H -0.0279 0.2000 0.3316 0.036 Uiso 1 1 calc R . .
C6 C 0.0622(3) 0.1195(6) 0.3219(5) 0.0339(13) Uani 1 1 d . . .
C7 C 0.0952(4) 0.0000 0.3184(7) 0.038(2) Uani 1 2 d S . .
H7A H 0.1407 0.0000 0.3137 0.046 Uiso 1 2 calc SR . .
C3 C -0.1127(4) 0.0000 0.3380(8) 0.0336(17) Uani 1 2 d SU . .
C11 C 0.1402(5) 0.5000 -0.1138(8) 0.0417(18) Uani 1 2 d SU . .
C4 C -0.0400(4) 0.0000 0.3326(7) 0.0288(16) Uani 1 2 d S . .
C9 C 0.1801(7) 0.5859(15) 0.0830(11) 0.050(3) Uani 0.50 1 d PU . .
C1 C -0.2150(4) 0.1032(9) 0.3463(13) 0.103(3) Uani 1 1 d U . .
H1A H -0.2372 0.1846 0.3457 0.123 Uiso 1 1 calc R . .
C14 C 0.1432(4) 0.5000 -0.2426(8) 0.0382(19) Uani 1 2 d S . .
C15 C 0.2028(5) 0.5000 -0.2822(9) 0.099(6) Uani 1 2 d S . .
H15A H 0.2433 0.5000 -0.2280 0.119 Uiso 1 2 calc SR . .
C18 C 0.0864(4) 0.5000 -0.3253(8) 0.052(3) Uani 1 2 d S . .
H18A H 0.0445 0.5000 -0.3027 0.063 Uiso 1 2 calc SR . .
C16 C 0.2028(5) 0.5000 -0.4031(9) 0.083(5) Uani 1 2 d S . .
H16A H 0.2441 0.5000 -0.4281 0.099 Uiso 1 2 calc SR . .
C17 C 0.0915(4) 0.5000 -0.4444(8) 0.060(3) Uani 1 2 d S . .
H17A H 0.0518 0.5000 -0.5005 0.072 Uiso 1 2 calc SR . .
N3 N 0.1486(3) 0.5000 -0.4837(6) 0.0302(14) Uani 1 2 d S . .


_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 2.073(5) . ?
Zn1 O1 2.073(5) 6_565 ?
Zn1 N1 2.146(6) 3 ?
Zn1 N3 2.189(6) 1_556 ?
Zn1 N2 2.190(7) . ?
Zn1 O2 2.598(8) 6_565 ?
Zn1 O2 2.598(8) . ?
O1 C8 1.238(9) . ?
O2 C8 1.229(9) . ?
N1 C1 1.254(10) . ?
N1 C1 1.254(10) 6 ?
N1 Zn1 2.146(6) 3_445 ?
N2 C13 1.287(14) . ?
N2 C13 1.287(14) 6_565 ?
N2 C9 1.372(14) . ?
N2 C9 1.372(14) 6_565 ?
C13 C13 1.38(3) 6_565 ?
C13 C12 1.388(19) . ?
C13 C9 1.647(18) 6_565 ?
C10 C9 1.345(19) . ?
C10 C11 1.461(15) . ?
C10 C12 1.745(19) 6_565 ?
C10 C10 1.85(3) 6_565 ?
C12 C11 1.305(15) . ?
C12 C12 1.36(3) 6_565 ?
C12 C10 1.745(19) 6_565 ?
C2 C3 1.307(10) . ?
C2 C1 1.362(12) . ?
C2 H2A 0.9300 . ?
C8 C6 1.500(8) . ?
C5 C6 1.382(8) . ?
C5 C4 1.389(6) . ?
C5 H5A 0.9300 . ?
C6 C7 1.374(7) . ?
C7 C6 1.374(7) 6 ?
C7 H7A 0.9300 . ?
C3 C2 1.307(10) 6 ?
C3 C4 1.480(10) . ?
C11 C12 1.305(15) 6_565 ?
C11 C10 1.461(15) 6_565 ?
C11 C14 1.482(13) . ?
C4 C5 1.389(6) 6 ?
C9 C13 1.647(18) 6_565 ?
C9 C9 1.72(3) 6_565 ?
C1 H1A 0.9300 . ?
C14 C18 1.344(12) . ?
C14 C15 1.361(13) . ?
C15 C16 1.380(14) . ?
C15 H15A 0.9300 . ?
C18 C17 1.381(13) . ?
C18 H18A 0.9300 . ?
C16 N3 1.294(11) . ?
C16 H16A 0.9300 . ?
C17 N3 1.311(11) . ?
C17 H17A 0.9300 . ?
N3 Zn1 2.189(6) 1_554 ?

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 O1 89.3(4) . 6_565 ?
O1 Zn1 N1 135.33(18) . 3 ?
O1 Zn1 N1 135.33(18) 6_565 3 ?
O1 Zn1 N3 88.47(18) . 1_556 ?
O1 Zn1 N3 88.47(18) 6_565 1_556 ?
N1 Zn1 N3 91.0(2) 3 1_556 ?
O1 Zn1 N2 93.05(19) . . ?
O1 Zn1 N2 93.05(19) 6_565 . ?
N1 Zn1 N2 86.9(3) 3 . ?
N3 Zn1 N2 177.9(2) 1_556 . ?
O1 Zn1 O2 143.1(2) . 6_565 ?
O1 Zn1 O2 53.9(2) 6_565 6_565 ?
N1 Zn1 O2 81.53(13) 3 6_565 ?
N3 Zn1 O2 91.84(15) 1_556 6_565 ?
N2 Zn1 O2 87.85(15) . 6_565 ?
O1 Zn1 O2 53.9(2) . . ?
O1 Zn1 O2 143.1(2) 6_565 . ?
N1 Zn1 O2 81.53(13) 3 . ?
N3 Zn1 O2 91.84(15) 1_556 . ?
N2 Zn1 O2 87.85(15) . . ?
O2 Zn1 O2 162.7(3) 6_565 . ?
C8 O1 Zn1 103.9(4) . . ?
C8 O2 Zn1 79.2(5) . . ?
C1 N1 C1 110.9(9) . 6 ?
C1 N1 Zn1 124.5(4) . 3_445 ?
C1 N1 Zn1 124.5(4) 6 3_445 ?
C13 N2 C13 64.6(14) . 6_565 ?
C13 N2 C9 115.9(9) . . ?
C13 N2 C9 76.5(9) 6_565 . ?
C13 N2 C9 76.5(9) . 6_565 ?
C13 N2 C9 115.9(9) 6_565 6_565 ?
C9 N2 C9 77.7(14) . 6_565 ?
C13 N2 Zn1 124.9(7) . . ?
C13 N2 Zn1 124.9(7) 6_565 . ?
C9 N2 Zn1 119.0(6) . . ?
C9 N2 Zn1 119.0(6) 6_565 . ?
N2 C13 C13 57.7(7) . 6_565 ?
N2 C13 C12 124.9(11) . . ?
C13 C13 C12 89.7(9) 6_565 . ?
N2 C13 C9 54.1(7) . 6_565 ?
C13 C13 C9 96.0(8) 6_565 6_565 ?
C12 C13 C9 92.7(10) . 6_565 ?
C9 C10 C11 117.6(12) . . ?
C9 C10 C12 89.9(11) . 6_565 ?
C11 C10 C12 47.0(7) . 6_565 ?
C9 C10 C10 87.3(9) . 6_565 ?
C11 C10 C10 50.7(6) . 6_565 ?
C12 C10 C10 82.0(7) 6_565 6_565 ?
C11 C12 C12 58.5(7) . 6_565 ?
C11 C12 C13 120.2(12) . . ?
C12 C12 C13 90.3(9) 6_565 . ?
C11 C12 C10 55.0(8) . 6_565 ?
C12 C12 C10 98.0(7) 6_565 6_565 ?
C13 C12 C10 85.9(10) . 6_565 ?
C3 C2 C1 121.3(8) . . ?
C3 C2 H2A 119.4 . . ?
C1 C2 H2A 119.4 . . ?
O2 C8 O1 122.8(7) . . ?
O2 C8 C6 118.3(7) . . ?
O1 C8 C6 118.8(6) . . ?
C6 C5 C4 120.7(5) . . ?
C6 C5 H5A 119.7 . . ?
C4 C5 H5A 119.7 . . ?
C7 C6 C5 119.4(5) . . ?
C7 C6 C8 119.9(5) . . ?
C5 C6 C8 120.8(6) . . ?
C6 C7 C6 121.1(7) 6 . ?
C6 C7 H7A 119.4 6 . ?
C6 C7 H7A 119.4 . . ?
C2 C3 C2 111.4(9) 6 . ?
C2 C3 C4 123.8(5) 6 . ?
C2 C3 C4 123.8(5) . . ?
C12 C11 C12 62.9(15) . 6_565 ?
C12 C11 C10 116.9(10) . . ?
C12 C11 C10 78.0(9) 6_565 . ?
C12 C11 C10 78.0(9) . 6_565 ?
C12 C11 C10 116.9(10) 6_565 6_565 ?
C10 C11 C10 78.5(13) . 6_565 ?
C12 C11 C14 123.1(9) . . ?
C12 C11 C14 123.1(9) 6_565 . ?
C10 C11 C14 119.5(8) . . ?
C10 C11 C14 119.5(8) 6_565 . ?
C5 C4 C5 118.8(7) . 6 ?
C5 C4 C3 120.6(3) . . ?
C5 C4 C3 120.6(3) 6 . ?
C10 C9 N2 123.5(12) . . ?
C10 C9 C13 91.4(10) . 6_565 ?
N2 C9 C13 49.4(7) . 6_565 ?
C10 C9 C9 92.7(9) . 6_565 ?
N2 C9 C9 51.1(7) . 6_565 ?
C13 C9 C9 84.0(8) 6_565 6_565 ?
N1 C1 C2 126.5(8) . . ?
N1 C1 H1A 116.8 . . ?
C2 C1 H1A 116.8 . . ?
C18 C14 C15 117.3(9) . . ?
C18 C14 C11 120.7(8) . . ?
C15 C14 C11 122.0(9) . . ?
C14 C15 C16 119.6(9) . . ?
C14 C15 H15A 120.2 . . ?
C16 C15 H15A 120.2 . . ?
C14 C18 C17 118.9(8) . . ?
C14 C18 H18A 120.6 . . ?
C17 C18 H18A 120.6 . . ?
N3 C16 C15 123.7(9) . . ?
N3 C16 H16A 118.1 . . ?
C15 C16 H16A 118.1 . . ?
N3 C17 C18 124.5(8) . . ?
N3 C17 H17A 117.8 . . ?
C18 C17 H17A 117.8 . . ?
C16 N3 C17 116.0(8) . . ?
C16 N3 Zn1 127.3(6) . 1_554 ?
C17 N3 Zn1 116.7(5) . 1_554 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.20
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.609
_refine_diff_density_min         -1.261
_refine_diff_density_rms         0.116
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1871007'
_audit_update_record             
;
2018-11-05 deposited with the CCDC.
2018-11-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H19 N3 O4 Zn'
_chemical_formula_weight         538.86

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/m

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.225 -0.103 0.500 1040.7 17.9
_platon_squeeze_details          
;
;



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

_cell_length_a                   20.2829(15)
_cell_length_b                   10.0000(9)
_cell_length_c                   15.6976(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.012(9)
_cell_angle_gamma                90.00
_cell_volume                     3102.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1350
_cell_measurement_theta_min      2.6760
_cell_measurement_theta_max      23.4520

_exptl_crystal_description       colorless
_exptl_crystal_colour            block
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.154
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    0.824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98470
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6173
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_av_sigmaI/netI    0.0928
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.66
_diffrn_reflns_theta_max         25.20
_reflns_number_total             2968
_reflns_number_gt                2022
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1269P)²+2.3697P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2968
_refine_ls_number_parameters     209
_refine_ls_number_restraints     67
_refine_ls_R_factor_all          0.1110
_refine_ls_R_factor_gt           0.0796
_refine_ls_wR_factor_ref         0.2395
_refine_ls_wR_factor_gt          0.2197
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.164
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.14079(5) 0.0000 -0.13111(6) 0.0314(4) Uani 1 2 d S . .
O1 O 0.0645(3) 0.1440(5) -0.1423(3) 0.0586(14) Uani 1 1 d . . .
O2 O 0.1588(3) 0.2545(7) -0.1302(5) 0.092(2) Uani 1 1 d U . .
N1 N 0.1488(4) 0.0000 0.0089(5) 0.0350(17) Uani 1 2 d S . .
N3 N -0.2508(4) 0.5000 -0.1137(5) 0.0371(18) Uani 1 2 d S . .
C1 C 0.2032(6) 0.0000 0.0701(8) 0.090(5) Uani 1 2 d S . .
H1A H 0.2447 0.0000 0.0542 0.108 Uiso 1 2 calc SR . .
C2 C 0.2029(7) 0.0000 0.1580(9) 0.093(4) Uani 1 2 d SU . .
H2A H 0.2437 0.0000 0.1993 0.112 Uiso 1 2 calc SR . .
C3 C 0.1442(5) 0.0000 0.1850(6) 0.049(3) Uani 1 2 d S . .
C4 C 0.0884(5) 0.0000 0.1237(6) 0.053(3) Uani 1 2 d S . .
H4A H 0.0466 0.0000 0.1387 0.064 Uiso 1 2 calc SR . .
C5 C 0.0920(5) 0.0000 0.0361(7) 0.068(4) Uani 1 2 d S . .
H5A H 0.0515 0.0000 -0.0059 0.081 Uiso 1 2 calc SR . .
C6 C 0.1455(3) 0.0000 0.2816(4) 0.075(4) Uani 1 2 d SG . .
C7 C 0.1990(3) -0.05274(14) 0.3439(4) 0.090(6) Uani 0.50 1 d PGU . .
C8 C 0.1946(3) -0.0605(4) 0.4309(4) 0.095(7) Uani 0.50 1 d PGU . .
C9 C 0.1367(3) -0.0155(9) 0.4555(4) 0.094(7) Uani 0.50 1 d PG . .
C10 C 0.0833(3) 0.0372(9) 0.3932(4) 0.080(8) Uani 0.50 1 d PG . .
C11 C 0.0877(3) 0.0449(5) 0.3062(3) 0.088(10) Uani 0.50 1 d PG . .
C12 C 0.1368(4) 0.0000(13) 0.5479(4) 0.082(4) Uani 1 2 d SG . .
C16 C 0.1723(6) 0.1104(14) 0.6165(4) 0.110(8) Uani 0.50 1 d PGU . .
C18 C -0.1476(4) 0.3929(8) -0.1092(5) 0.087(2) Uani 1 1 d GU . .
H18A H -0.1253 0.3110 -0.1034 0.105 Uiso 1 1 calc R . .
C19 C -0.1133(4) 0.5000 -0.1171(7) 0.044(2) Uani 1 2 d SU . .
C17 C -0.2151(4) 0.3947(9) -0.1089(9) 0.094(3) Uani 1 1 d U . .
H17A H -0.2362 0.3132 -0.1049 0.113 Uiso 1 1 calc R . .
C20 C -0.0415(4) 0.5000 -0.1225(6) 0.038(2) Uani 1 2 d S . .
C21 C -0.0069(3) 0.3797(6) -0.1264(5) 0.0402(16) Uani 1 1 d . . .
H21A H -0.0293 0.2989 -0.1253 0.048 Uiso 1 1 calc R . .
C22 C 0.0604(3) 0.3797(6) -0.1319(4) 0.0385(15) Uani 1 1 d . . .
C23 C 0.0938(4) 0.5000 -0.1343(6) 0.040(2) Uani 1 2 d S . .
H23A H 0.1389 0.5000 -0.1377 0.047 Uiso 1 2 calc SR . .
C24 C 0.0974(4) 0.2507(9) -0.1357(5) 0.054(2) Uani 1 1 d . . .
C13 C 0.1004(11) 0.073(2) 0.5864(13) 0.098(7) Uani 0.50 1 d PU . .
C14 C 0.1033(10) 0.076(2) 0.6714(11) 0.082(6) Uani 0.50 1 d P . .
C15 C 0.1713(13) 0.102(2) 0.6963(10) 0.087(7) Uani 0.50 1 d P . .
N2 N 0.1362(4) 0.0000 0.7268(6) 0.051(2) Uani 1 2 d SU . .


_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 2.091(5) 6 ?
Zn1 O1 2.091(5) . ?
Zn1 N3 2.154(7) 3_545 ?
Zn1 N1 2.166(7) . ?
Zn1 N2 2.211(8) 1_554 ?
Zn1 O2 2.570(7) 6 ?
Zn1 O2 2.570(7) . ?
O1 C24 1.250(10) . ?
O2 C24 1.230(10) . ?
N1 C1 1.290(13) . ?
N1 C5 1.316(12) . ?
N3 C17 1.270(9) 6_565 ?
N3 C17 1.270(9) . ?
N3 Zn1 2.154(7) 3_455 ?
C1 C2 1.382(17) . ?
C1 H1A 0.9300 . ?
C2 C3 1.349(16) . ?
C2 H2A 0.9300 . ?
C3 C4 1.310(14) . ?
C3 C6 1.511(11) . ?
C4 C5 1.393(13) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 C11 1.390(3) 6 ?
C6 C7 1.3901 . ?
C6 C11 1.3899 . ?
C6 C7 1.3901(11) 6 ?
C7 C7 1.055(3) 6 ?
C7 C8 1.3900 . ?
C7 C8 1.791(5) 6 ?
C8 C8 1.210(8) 6 ?
C8 C9 1.3900 . ?
C8 C9 1.519(9) 6 ?
C8 C7 1.7911(18) 6 ?
C9 C9 0.310(17) 6 ?
C9 C10 1.304(3) 6 ?
C9 C10 1.3900 . ?
C9 C12 1.4587 . ?
C9 C8 1.519(4) 6 ?
C10 C10 0.744(18) 6 ?
C10 C9 1.304(3) 6 ?
C10 C11 1.3900 . ?
C10 C11 1.612(5) 6 ?
C11 C11 0.898(10) 6 ?
C11 C10 1.612(9) 6 ?
C12 C13 1.28(2) . ?
C12 C13 1.28(2) 6 ?
C12 C9 1.4587(19) 6 ?
C12 C16 1.5954 . ?
C12 C16 1.595(19) 6 ?
C16 C15 1.261(16) . ?
C16 C13 1.48(3) . ?
C16 C14 1.83(2) . ?
C18 C19 1.299(9) . ?
C18 C17 1.370(11) . ?
C18 H18A 0.9300 . ?
C19 C18 1.299(11) 6_565 ?
C19 C20 1.477(12) . ?
C17 H17A 0.9300 . ?
C20 C21 1.401(7) 6_565 ?
C20 C21 1.401(7) . ?
C21 C22 1.387(8) . ?
C21 H21A 0.9300 . ?
C22 C23 1.385(7) . ?
C22 C24 1.500(9) . ?
C23 C22 1.385(7) 6_565 ?
C23 H23A 0.9300 . ?
C13 C14 1.32(3) . ?
C13 C13 1.46(5) 6 ?
C14 N2 1.235(17) . ?
C14 C15 1.37(3) . ?
C14 C14 1.53(4) 6 ?
C15 N2 1.386(19) . ?
N2 C14 1.235(18) 6 ?
N2 C15 1.386(19) 6 ?
N2 Zn1 2.211(8) 1_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
O1 Zn1 O1 87.0(3) 6 . ?
O1 Zn1 N3 136.49(17) 6 3_545 ?
O1 Zn1 N3 136.49(17) . 3_545 ?
O1 Zn1 N1 88.3(2) 6 . ?
O1 Zn1 N1 88.3(2) . . ?
N3 Zn1 N1 91.7(3) 3_545 . ?
O1 Zn1 N2 93.0(2) 6 1_554 ?
O1 Zn1 N2 93.0(2) . 1_554 ?
N3 Zn1 N2 86.4(3) 3_545 1_554 ?
N1 Zn1 N2 178.2(3) . 1_554 ?
O1 Zn1 O2 54.6(2) 6 6 ?
O1 Zn1 O2 141.6(2) . 6 ?
N3 Zn1 O2 81.93(13) 3_545 6 ?
N1 Zn1 O2 90.94(16) . 6 ?
N2 Zn1 O2 88.80(16) 1_554 6 ?
O1 Zn1 O2 141.6(2) 6 . ?
O1 Zn1 O2 54.6(2) . . ?
N3 Zn1 O2 81.93(13) 3_545 . ?
N1 Zn1 O2 90.94(16) . . ?
N2 Zn1 O2 88.80(16) 1_554 . ?
O2 Zn1 O2 163.8(2) 6 . ?
C24 O1 Zn1 102.2(5) . . ?
C24 O2 Zn1 80.2(5) . . ?
C1 N1 C5 115.0(9) . . ?
C1 N1 Zn1 127.7(7) . . ?
C5 N1 Zn1 117.3(6) . . ?
C17 N3 C17 111.9(9) 6_565 . ?
C17 N3 Zn1 124.0(5) 6_565 3_455 ?
C17 N3 Zn1 124.0(5) . 3_455 ?
N1 C1 C2 123.2(11) . . ?
N1 C1 H1A 118.4 . . ?
C2 C1 H1A 118.4 . . ?
C3 C2 C1 121.1(13) . . ?
C3 C2 H2A 119.5 . . ?
C1 C2 H2A 119.5 . . ?
C4 C3 C2 116.5(10) . . ?
C4 C3 C6 123.6(8) . . ?
C2 C3 C6 119.9(10) . . ?
C3 C4 C5 119.8(9) . . ?
C3 C4 H4A 120.1 . . ?
C5 C4 H4A 120.1 . . ?
N1 C5 C4 124.3(10) . . ?
N1 C5 H5A 117.8 . . ?
C4 C5 H5A 117.8 . . ?
C11 C6 C7 104.76(19) 6 . ?
C11 C6 C11 37.7(4) 6 . ?
C7 C6 C11 120.0 . . ?
C11 C6 C7 120.00(11) 6 6 ?
C7 C6 C7 44.59(11) . 6 ?
C11 C6 C7 104.76(5) . 6 ?
C11 C6 C3 117.0(4) 6 . ?
C7 C6 C3 122.7(4) . . ?
C11 C6 C3 117.0(4) . . ?
C7 C6 C3 122.7(5) 6 . ?
C7 C7 C6 67.7 6 . ?
C7 C7 C8 93.2 6 . ?
C6 C7 C8 120.0 . . ?
C7 C7 C8 50.8(2) 6 6 ?
C6 C7 C8 97.57(13) . 6 ?
C8 C7 C8 42.4(2) . 6 ?
C8 C8 C9 71.1 6 . ?
C8 C8 C7 86.8 6 . ?
C9 C8 C7 120.0 . . ?
C8 C8 C9 60.0(6) 6 6 ?
C9 C8 C9 11.1(6) . 6 ?
C7 C8 C9 116.5(2) . 6 ?
C8 C8 C7 50.79(7) 6 6 ?
C9 C8 C7 101.4 . 6 ?
C7 C8 C7 36.02(7) . 6 ?
C9 C8 C7 93.0(4) 6 6 ?
C9 C9 C10 99.6(8) 6 6 ?
C9 C9 C8 108.9 6 . ?
C10 C9 C8 110.4(3) 6 . ?
C9 C9 C10 67.7 6 . ?
C10 C9 C10 31.8(8) 6 . ?
C8 C9 C10 120.0 . . ?
C9 C9 C12 83.9 6 . ?
C10 C9 C12 125.3 6 . ?
C8 C9 C12 119.9 . . ?
C10 C9 C12 119.1 . . ?
C9 C9 C8 60.0(3) 6 6 ?
C10 C9 C8 116.8(4) 6 6 ?
C8 C9 C8 48.9(3) . 6 ?
C10 C9 C8 98.95(15) . 6 ?
C12 C9 C8 111.84(10) . 6 ?
C10 C10 C9 80.4(7) 6 6 ?
C10 C10 C9 67.7 6 . ?
C9 C10 C9 12.7(7) 6 . ?
C10 C10 C11 93.2 6 . ?
C9 C10 C11 121.3 6 . ?
C9 C10 C11 120.0 . . ?
C10 C10 C11 59.4(3) 6 6 ?
C9 C10 C11 110.8(6) 6 6 ?
C9 C10 C11 102.70(17) . 6 ?
C11 C10 C11 33.8(3) . 6 ?
C11 C11 C10 86.8 6 . ?
C11 C11 C6 71.1 6 . ?
C10 C11 C6 120.0 . . ?
C11 C11 C10 59.4(6) 6 6 ?
C10 C11 C10 27.4(6) . 6 ?
C6 C11 C10 106.4(3) . 6 ?
C13 C12 C13 70(2) . 6 ?
C13 C12 C9 122.4(12) . 6 ?
C13 C12 C9 131.1(12) 6 6 ?
C13 C12 C9 131.1(9) . . ?
C13 C12 C9 122.4(10) 6 . ?
C9 C12 C9 12.2(7) 6 . ?
C13 C12 C16 60.6(12) . . ?
C13 C12 C16 107.3(10) 6 . ?
C9 C12 C16 119.8(6) 6 . ?
C9 C12 C16 130.1 . . ?
C13 C12 C16 107.3(9) . 6 ?
C13 C12 C16 60.6(12) 6 6 ?
C9 C12 C16 130.1(10) 6 6 ?
C9 C12 C16 119.8(5) . 6 ?
C16 C12 C16 87.5(7) . 6 ?
C15 C16 C13 93.7(15) . . ?
C15 C16 C12 121.1(13) . . ?
C13 C16 C12 49.2(9) . . ?
C15 C16 C14 48.3(12) . . ?
C13 C16 C14 45.6(10) . . ?
C12 C16 C14 85.0(9) . . ?
C19 C18 C17 123.2(7) . . ?
C19 C18 H18A 118.4 . . ?
C17 C18 H18A 118.4 . . ?
C18 C19 C18 111.1(10) . 6_565 ?
C18 C19 C20 124.2(5) . . ?
C18 C19 C20 124.2(5) 6_565 . ?
N3 C17 C18 124.6(8) . . ?
N3 C17 H17A 117.7 . . ?
C18 C17 H17A 117.7 . . ?
C21 C20 C21 118.3(8) 6_565 . ?
C21 C20 C19 120.8(4) 6_565 . ?
C21 C20 C19 120.8(4) . . ?
C22 C21 C20 120.8(6) . . ?
C22 C21 H21A 119.6 . . ?
C20 C21 H21A 119.6 . . ?
C23 C22 C21 119.7(6) . . ?
C23 C22 C24 119.6(6) . . ?
C21 C22 C24 120.7(6) . . ?
C22 C23 C22 120.6(8) . 6_565 ?
C22 C23 H23A 119.7 . . ?
C22 C23 H23A 119.7 6_565 . ?
O2 C24 O1 122.9(7) . . ?
O2 C24 C22 118.6(8) . . ?
O1 C24 C22 118.4(6) . . ?
C12 C13 C14 126.1(16) . . ?
C12 C13 C13 55.2(12) . 6 ?
C14 C13 C13 91.4(14) . 6 ?
C12 C13 C16 70.2(11) . . ?
C14 C13 C16 81.6(15) . . ?
C13 C13 C16 104.6(10) 6 . ?
N2 C14 C13 126.1(16) . . ?
N2 C14 C15 64.1(12) . . ?
C13 C14 C15 96.1(17) . . ?
N2 C14 C14 51.7(11) . 6 ?
C13 C14 C14 88.6(14) . 6 ?
C15 C14 C14 100.6(13) . 6 ?
N2 C14 C16 95.6(12) . . ?
C13 C14 C16 52.8(12) . . ?
C15 C14 C16 43.4(9) . . ?
C14 C14 C16 100.6(7) 6 . ?
C16 C15 C14 88.2(16) . . ?
C16 C15 N2 121.2(18) . . ?
C14 C15 N2 53.2(12) . . ?
C14 N2 C14 77(2) . 6 ?
C14 N2 C15 116.7(12) . 6 ?
C14 N2 C15 62.7(13) 6 6 ?
C14 N2 C15 62.7(13) . . ?
C14 N2 C15 116.7(12) 6 . ?
C15 N2 C15 94(2) 6 . ?
C14 N2 Zn1 127.1(9) . 1_556 ?
C14 N2 Zn1 127.1(9) 6 1_556 ?
C15 N2 Zn1 116.1(8) 6 1_556 ?
C15 N2 Zn1 116.1(8) . 1_556 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.20
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.017
_refine_diff_density_min         -0.729
_refine_diff_density_rms         0.103
