# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2016

####################################################################### 
# 
# 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_pp
_database_code_depnum_ccdc_archive 'CCDC 1438481'
_audit_update_record             
;
2015-11-24 deposited with the CCDC.
2016-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H15 N3 O9 Zn'
_chemical_formula_weight         470.69

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           Orthorhombic
_symmetry_space_group_name_H-M   Pbcn

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

_cell_length_a                   27.841(6)
_cell_length_b                   7.5266(15)
_cell_length_c                   17.413(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3648.9(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       green
_exptl_crystal_colour            block
_exptl_crystal_size_max          0.586
_exptl_crystal_size_mid          0.253
_exptl_crystal_size_min          0.103
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1920
_exptl_absorpt_coefficient_mu    1.407
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.674
_exptl_absorpt_correction_T_max  1.000
_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 RAXIS-RAPID'
_diffrn_measurement_method       psi-scan
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            31201
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_av_sigmaI/netI    0.0363
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4171
_reflns_number_gt                3048
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.0835P)²+6.6396P] 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         4171
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1598
_refine_ls_wR_factor_gt          0.1470
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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 0.097472(15) 0.30632(7) 0.23386(2) 0.02632(17) Uani 1 1 d . . .
O1 O 0.07865(10) 0.0977(4) 0.29679(17) 0.0351(7) Uani 1 1 d . . .
O2 O 0.06407(10) 0.5108(4) 0.27706(15) 0.0321(7) Uani 1 1 d . . .
O3 O 0.07634(10) 0.2929(4) 0.12663(15) 0.0333(7) Uani 1 1 d . . .
O4 O 0.01028(11) 0.1364(5) 0.14943(17) 0.0421(8) Uani 1 1 d . . .
O5 O 0.11345(11) 0.4671(6) 0.37450(18) 0.0520(10) Uani 1 1 d . . .
O6 O 0.1170(2) -0.0082(10) 0.9391(5) 0.152(3) Uani 1 1 d . . .
O7 O 0.1715(3) 0.0103(13) 0.8680(4) 0.147(3) Uani 1 1 d . . .
O8 O 0.1803(4) 0.0894(18) 0.9779(6) 0.245(6) Uani 1 1 d . . .
O1W O 0.7208(3) 0.0205(13) 0.0628(4) 0.157(3) Uani 1 1 d . . .
C1 C 0.35514(13) 0.3273(6) 0.1926(2) 0.0287(9) Uani 1 1 d . . .
H1 H 0.3483 0.3726 0.2411 0.034 Uiso 1 1 calc R . .
C2 C 0.20439(15) 0.3213(7) 0.2632(2) 0.0362(10) Uani 1 1 d . . .
H2 H 0.1959 0.3449 0.3139 0.043 Uiso 1 1 calc R . .
C3 C 0.25278(15) 0.3121(7) 0.2444(2) 0.0366(10) Uani 1 1 d . . .
H3 H 0.2760 0.3283 0.2822 0.044 Uiso 1 1 calc R . .
C4 C 0.26655(13) 0.2785(5) 0.1692(2) 0.0239(8) Uani 1 1 d . . .
C5 C 0.31773(12) 0.2676(5) 0.1451(2) 0.0227(7) Uani 1 1 d . . .
C6 C 0.33032(14) 0.2015(6) 0.0734(2) 0.0334(9) Uani 1 1 d . . .
H6 H 0.3064 0.1619 0.0402 0.040 Uiso 1 1 calc R . .
C7 C 0.37750(14) 0.1938(6) 0.0507(2) 0.0303(9) Uani 1 1 d . . .
H7 H 0.3852 0.1487 0.0026 0.036 Uiso 1 1 calc R . .
C8 C 0.40207(13) 0.3187(6) 0.1673(2) 0.0279(8) Uani 1 1 d . . .
H8 H 0.4266 0.3600 0.1988 0.033 Uiso 1 1 calc R . .
C9 C 0.46285(12) 0.2335(5) 0.0746(2) 0.0215(7) Uani 1 1 d . . .
C10 C 0.47528(13) 0.2753(5) 0.0001(2) 0.0241(8) Uani 1 1 d . . .
H10 H 0.4527 0.3229 -0.0335 0.029 Uiso 1 1 calc R . .
C11 C 0.49534(12) 0.1618(5) 0.1263(2) 0.0222(8) Uani 1 1 d . . .
H11 H 0.4860 0.1345 0.1762 0.027 Uiso 1 1 calc R . .
C12 C 0.54223(12) 0.1316(5) 0.1020(2) 0.0221(7) Uani 1 1 d . . .
C13 C 0.55543(13) 0.1733(5) 0.0271(2) 0.0239(8) Uani 1 1 d . . .
H13 H 0.5868 0.1531 0.0109 0.029 Uiso 1 1 calc R . .
C14 C 0.03638(13) 0.2235(5) 0.1069(2) 0.0252(8) Uani 1 1 d . . .
C15 C 0.02233(13) 0.2554(5) 0.0238(2) 0.0213(7) Uani 1 1 d . . .
C16 C 0.07699(13) 0.5322(6) 0.3471(2) 0.0276(8) Uani 1 1 d . . .
C17 C 0.23003(14) 0.2556(7) 0.1159(2) 0.0351(10) Uani 1 1 d . . .
H17 H 0.2375 0.2345 0.0647 0.042 Uiso 1 1 calc R . .
C18 C 0.18276(14) 0.2640(7) 0.1385(2) 0.0349(10) Uani 1 1 d . . .
H18 H 0.1590 0.2457 0.1019 0.042 Uiso 1 1 calc R . .
N1 N 0.16937(11) 0.2975(5) 0.2112(2) 0.0282(7) Uani 1 1 d . . .
N2 N 0.41277(10) 0.2513(4) 0.09782(18) 0.0205(6) Uani 1 1 d . . .
N3 N 0.15733(15) 0.0407(6) 0.9267(2) 0.0479(11) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O2 1.949(3) . ?
Zn1 O3 1.960(3) . ?
Zn1 O1 1.985(3) . ?
Zn1 N1 2.041(3) . ?
O2 C16 1.281(5) . ?
O3 C14 1.276(5) . ?
O4 C14 1.227(5) . ?
O5 C16 1.224(5) . ?
O6 N3 1.200(7) . ?
O7 N3 1.120(7) . ?
O8 N3 1.158(8) . ?
C1 C8 1.380(5) . ?
C1 C5 1.404(5) . ?
C1 H1 0.9300 . ?
C2 N1 1.343(5) . ?
C2 C3 1.388(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(5) . ?
C3 H3 0.9300 . ?
C4 C17 1.387(5) . ?
C4 C5 1.488(5) . ?
C5 C6 1.388(5) . ?
C6 C7 1.373(5) . ?
C6 H6 0.9300 . ?
C7 N2 1.350(5) . ?
C7 H7 0.9300 . ?
C8 N2 1.346(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.378(5) . ?
C9 C11 1.386(5) . ?
C9 N2 1.458(4) . ?
C10 C15 1.394(5) 3 ?
C10 H10 0.9300 . ?
C11 C12 1.391(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.391(5) . ?
C12 C16 1.511(5) 6_656 ?
C13 C15 1.386(5) 3 ?
C13 H13 0.9300 . ?
C14 C15 1.519(5) . ?
C15 C13 1.386(5) 3_455 ?
C15 C10 1.394(5) 3_455 ?
C16 C12 1.511(5) 6_566 ?
C17 C18 1.375(5) . ?
C17 H17 0.9300 . ?
C18 N1 1.343(5) . ?
C18 H18 0.9300 . ?

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
O2 Zn1 O3 105.37(12) . . ?
O2 Zn1 O1 106.60(12) . . ?
O3 Zn1 O1 113.93(13) . . ?
O2 Zn1 N1 124.61(14) . . ?
O3 Zn1 N1 96.24(13) . . ?
O1 Zn1 N1 109.86(13) . . ?
C16 O2 Zn1 109.4(2) . . ?
C14 O3 Zn1 122.6(3) . . ?
C8 C1 C5 119.9(4) . . ?
C8 C1 H1 120.0 . . ?
C5 C1 H1 120.0 . . ?
N1 C2 C3 122.6(4) . . ?
N1 C2 H2 118.7 . . ?
C3 C2 H2 118.7 . . ?
C2 C3 C4 120.0(4) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C17 C4 C3 116.8(3) . . ?
C17 C4 C5 120.4(3) . . ?
C3 C4 C5 122.8(4) . . ?
C6 C5 C1 117.2(3) . . ?
C6 C5 C4 121.0(3) . . ?
C1 C5 C4 121.7(3) . . ?
C7 C6 C5 121.0(4) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
N2 C7 C6 120.5(4) . . ?
N2 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
N2 C8 C1 120.9(4) . . ?
N2 C8 H8 119.5 . . ?
C1 C8 H8 119.5 . . ?
C10 C9 C11 122.4(3) . . ?
C10 C9 N2 118.7(3) . . ?
C11 C9 N2 118.7(3) . . ?
C9 C10 C15 118.6(3) . 3 ?
C9 C10 H10 120.7 . . ?
C15 C10 H10 120.7 3 . ?
C9 C11 C12 118.6(3) . . ?
C9 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
C13 C12 C11 119.7(3) . . ?
C13 C12 C16 119.5(3) . 6_656 ?
C11 C12 C16 120.2(3) . 6_656 ?
C15 C13 C12 120.7(3) 3 . ?
C15 C13 H13 119.6 3 . ?
C12 C13 H13 119.6 . . ?
O4 C14 O3 125.0(4) . . ?
O4 C14 C15 120.5(3) . . ?
O3 C14 C15 114.6(3) . . ?
C13 C15 C10 119.9(3) 3_455 3_455 ?
C13 C15 C14 119.9(3) 3_455 . ?
C10 C15 C14 120.0(3) 3_455 . ?
O5 C16 O2 123.6(4) . . ?
O5 C16 C12 120.0(3) . 6_566 ?
O2 C16 C12 116.2(3) . 6_566 ?
C18 C17 C4 120.3(4) . . ?
C18 C17 H17 119.8 . . ?
C4 C17 H17 119.8 . . ?
N1 C18 C17 122.9(4) . . ?
N1 C18 H18 118.5 . . ?
C17 C18 H18 118.5 . . ?
C2 N1 C18 117.3(3) . . ?
C2 N1 Zn1 125.3(3) . . ?
C18 N1 Zn1 117.4(3) . . ?
C8 N2 C7 120.4(3) . . ?
C8 N2 C9 119.7(3) . . ?
C7 N2 C9 119.8(3) . . ?
O7 N3 O8 125.0(9) . . ?
O7 N3 O6 115.5(7) . . ?
O8 N3 O6 118.4(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 Zn1 O2 C16 -178.2(3) . . . . ?
O1 Zn1 O2 C16 60.4(3) . . . . ?
N1 Zn1 O2 C16 -69.1(3) . . . . ?
O2 Zn1 O3 C14 -80.6(3) . . . . ?
O1 Zn1 O3 C14 35.9(4) . . . . ?
N1 Zn1 O3 C14 150.9(3) . . . . ?
N1 C2 C3 C4 0.5(8) . . . . ?
C2 C3 C4 C17 0.0(7) . . . . ?
C2 C3 C4 C5 179.8(4) . . . . ?
C8 C1 C5 C6 -0.1(6) . . . . ?
C8 C1 C5 C4 -178.5(4) . . . . ?
C17 C4 C5 C6 -12.4(6) . . . . ?
C3 C4 C5 C6 167.8(4) . . . . ?
C17 C4 C5 C1 165.9(4) . . . . ?
C3 C4 C5 C1 -13.9(6) . . . . ?
C1 C5 C6 C7 0.6(6) . . . . ?
C4 C5 C6 C7 179.1(4) . . . . ?
C5 C6 C7 N2 -0.3(7) . . . . ?
C5 C1 C8 N2 -0.9(6) . . . . ?
C11 C9 C10 C15 -0.2(6) . . . 3 ?
N2 C9 C10 C15 -174.9(3) . . . 3 ?
C10 C9 C11 C12 0.2(6) . . . . ?
N2 C9 C11 C12 174.9(3) . . . . ?
C9 C11 C12 C13 -0.1(6) . . . . ?
C9 C11 C12 C16 -172.1(4) . . . 6_656 ?
C11 C12 C13 C15 -0.1(6) . . . 3 ?
C16 C12 C13 C15 172.0(4) 6_656 . . 3 ?
Zn1 O3 C14 O4 -11.0(6) . . . . ?
Zn1 O3 C14 C15 169.4(2) . . . . ?
O4 C14 C15 C13 -168.9(4) . . . 3_455 ?
O3 C14 C15 C13 10.8(5) . . . 3_455 ?
O4 C14 C15 C10 15.7(6) . . . 3_455 ?
O3 C14 C15 C10 -164.7(4) . . . 3_455 ?
Zn1 O2 C16 O5 18.4(5) . . . . ?
Zn1 O2 C16 C12 -156.5(3) . . . 6_566 ?
C3 C4 C17 C18 -0.9(7) . . . . ?
C5 C4 C17 C18 179.3(4) . . . . ?
C4 C17 C18 N1 1.3(8) . . . . ?
C3 C2 N1 C18 -0.1(7) . . . . ?
C3 C2 N1 Zn1 179.4(4) . . . . ?
C17 C18 N1 C2 -0.8(7) . . . . ?
C17 C18 N1 Zn1 179.6(4) . . . . ?
O2 Zn1 N1 C2 58.9(4) . . . . ?
O3 Zn1 N1 C2 172.4(4) . . . . ?
O1 Zn1 N1 C2 -69.3(4) . . . . ?
O2 Zn1 N1 C18 -121.6(3) . . . . ?
O3 Zn1 N1 C18 -8.0(4) . . . . ?
O1 Zn1 N1 C18 110.2(3) . . . . ?
C1 C8 N2 C7 1.3(6) . . . . ?
C1 C8 N2 C9 -176.2(4) . . . . ?
C6 C7 N2 C8 -0.7(6) . . . . ?
C6 C7 N2 C9 176.8(4) . . . . ?
C10 C9 N2 C8 -139.3(4) . . . . ?
C11 C9 N2 C8 45.8(5) . . . . ?
C10 C9 N2 C7 43.2(5) . . . . ?
C11 C9 N2 C7 -131.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.859
_refine_diff_density_min         -0.774
_refine_diff_density_rms         0.106
####################################################################### 
# 
# 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_p
_database_code_depnum_ccdc_archive 'CCDC 1438482'
_audit_update_record             
;
2015-11-24 deposited with the CCDC.
2016-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H17 N3 O10 Zn'
_chemical_formula_weight         500.72

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6695(19)
_cell_length_b                   10.135(3)
_cell_length_c                   10.898(2)
_cell_angle_alpha                86.47(3)
_cell_angle_beta                 89.99(3)
_cell_angle_gamma                62.48(2)
_cell_volume                     944.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.564
_exptl_crystal_size_mid          0.245
_exptl_crystal_size_min          0.158
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.760
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    1.368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.712
_exptl_absorpt_correction_T_max  1.000
_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 RAXIS-RAPID'
_diffrn_measurement_method       psi-scan
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9325
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         27.49
_reflns_number_total             4291
_reflns_number_gt                3621
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.0688P)²+0.5255P] 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         4291
_refine_ls_number_parameters     284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.1144
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_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 0.33867(3) -0.21640(3) 0.04639(3) 0.02187(12) Uani 1 1 d . . .
O1 O 0.5409(2) -0.3221(2) -0.03760(18) 0.0292(4) Uani 1 1 d . . .
O2 O -0.3815(2) 0.8150(3) 1.06475(19) 0.0344(5) Uani 1 1 d . . .
O3 O 0.2803(3) 0.6439(3) 0.8403(2) 0.0405(5) Uani 1 1 d . . .
O4 O 0.1544(2) -0.2440(2) 0.00396(19) 0.0317(5) Uani 1 1 d . . .
O5 O 0.4222(2) -0.4016(2) 0.18299(19) 0.0321(5) Uani 1 1 d . . .
O6 O 0.2780(3) -0.0259(2) -0.08360(19) 0.0335(5) Uani 1 1 d . . .
N1 N 0.2510(3) -0.0739(3) 0.1878(2) 0.0232(5) Uani 1 1 d . . .
N2 N -0.0096(3) 0.3875(2) 0.68084(19) 0.0203(4) Uani 1 1 d . . .
C1 C 0.1065(3) -0.0357(3) 0.2282(2) 0.0268(6) Uani 1 1 d . . .
H1 H 0.0451 -0.0695 0.1882 0.032 Uiso 1 1 calc R . .
C2 C 0.0454(3) 0.0518(3) 0.3267(2) 0.0265(6) Uani 1 1 d . . .
H2 H -0.0550 0.0764 0.3518 0.032 Uiso 1 1 calc R . .
C3 C 0.3366(3) -0.0225(3) 0.2454(3) 0.0288(6) Uani 1 1 d . . .
H3 H 0.4357 -0.0465 0.2174 0.035 Uiso 1 1 calc R . .
C4 C 0.2843(3) 0.0643(3) 0.3443(3) 0.0297(6) Uani 1 1 d . . .
H4 H 0.3478 0.0973 0.3821 0.036 Uiso 1 1 calc R . .
C5 C 0.1363(3) 0.1022(3) 0.3874(2) 0.0224(5) Uani 1 1 d . . .
C6 C 0.0801(3) 0.1964(3) 0.4935(2) 0.0225(5) Uani 1 1 d . . .
C7 C 0.1831(3) 0.1783(3) 0.5896(2) 0.0272(6) Uani 1 1 d . . .
H7 H 0.2845 0.1009 0.5905 0.033 Uiso 1 1 calc R . .
C8 C 0.1373(3) 0.2726(3) 0.6828(2) 0.0245(5) Uani 1 1 d . . .
H8 H 0.2067 0.2580 0.7474 0.029 Uiso 1 1 calc R . .
C9 C -0.0730(3) 0.3076(3) 0.4991(2) 0.0275(6) Uani 1 1 d . . .
H9 H -0.1469 0.3171 0.4400 0.033 Uiso 1 1 calc R . .
C10 C -0.1157(3) 0.4042(3) 0.5926(3) 0.0276(6) Uani 1 1 d . . .
H10 H -0.2173 0.4805 0.5946 0.033 Uiso 1 1 calc R . .
C11 C -0.0447(3) 0.4980(3) 0.7710(2) 0.0185(5) Uani 1 1 d . . .
C12 C 0.0689(3) 0.5403(3) 0.7946(2) 0.0196(5) Uani 1 1 d . . .
H12 H 0.1612 0.5019 0.7520 0.023 Uiso 1 1 calc R . .
C13 C -0.1865(3) 0.5563(3) 0.8295(2) 0.0198(5) Uani 1 1 d . . .
H13 H -0.2621 0.5277 0.8107 0.024 Uiso 1 1 calc R . .
C14 C 0.1695(3) 0.6835(3) 0.9106(3) 0.0234(5) Uani 1 1 d . . .
C15 C -0.3612(3) 0.7226(3) 0.9872(2) 0.0204(5) Uani 1 1 d . . .
C16 C -0.2122(3) 0.6596(3) 0.9178(2) 0.0179(5) Uani 1 1 d . . .
C17 C -0.0967(3) 0.7001(3) 0.9448(2) 0.0191(5) Uani 1 1 d . . .
H17 H -0.1131 0.7669 1.0047 0.023 Uiso 1 1 calc R . .
C18 C 0.0426(3) 0.6416(3) 0.8833(2) 0.0181(5) Uani 1 1 d . . .
N3 N 0.5269(3) 0.6792(3) 0.4520(2) 0.0384(6) Uani 1 1 d . . .
O7 O 0.5719(3) 0.7234(4) 0.5408(3) 0.0588(8) Uani 1 1 d . . .
O8 O 0.3908(4) 0.6991(5) 0.4446(3) 0.0758(10) Uani 1 1 d . . .
O9 O 0.6162(4) 0.6164(5) 0.3712(3) 0.0780(10) Uani 1 1 d . . .
O1W O 0.6645(3) 0.1543(3) 0.2991(2) 0.0508(6) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O4 1.986(2) . ?
Zn1 O1 1.9983(19) . ?
Zn1 N1 2.079(2) . ?
Zn1 O5 2.156(2) . ?
Zn1 O6 2.167(2) . ?
O1 C15 1.260(3) 1_644 ?
O2 C15 1.248(3) . ?
O3 C14 1.240(4) . ?
O4 C14 1.261(3) 1_544 ?
N1 C3 1.338(3) . ?
N1 C1 1.348(4) . ?
N2 C10 1.351(3) . ?
N2 C8 1.357(3) . ?
N2 C11 1.456(3) . ?
C1 C2 1.386(4) . ?
C1 H1 0.9300 . ?
C2 C5 1.388(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.484(3) . ?
C6 C7 1.389(4) . ?
C6 C9 1.390(4) . ?
C7 C8 1.367(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.384(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.380(3) . ?
C11 C13 1.391(3) . ?
C12 C18 1.390(3) . ?
C12 H12 0.9300 . ?
C13 C16 1.402(3) . ?
C13 H13 0.9300 . ?
C14 O4 1.261(3) 1_566 ?
C14 C18 1.508(3) . ?
C15 O1 1.260(3) 1_466 ?
C15 C16 1.505(3) . ?
C16 C17 1.393(3) . ?
C17 C18 1.388(3) . ?
C17 H17 0.9300 . ?
N3 O9 1.220(4) . ?
N3 O8 1.237(4) . ?
N3 O7 1.249(4) . ?

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
O4 Zn1 O1 121.69(8) . . ?
O4 Zn1 N1 100.52(9) . . ?
O1 Zn1 N1 137.73(9) . . ?
O4 Zn1 O5 91.77(9) . . ?
O1 Zn1 O5 88.14(9) . . ?
N1 Zn1 O5 88.38(9) . . ?
O4 Zn1 O6 95.12(9) . . ?
O1 Zn1 O6 88.68(9) . . ?
N1 Zn1 O6 89.83(9) . . ?
O5 Zn1 O6 173.08(8) . . ?
C15 O1 Zn1 113.78(16) 1_644 . ?
C14 O4 Zn1 114.54(18) 1_544 . ?
C3 N1 C1 117.7(2) . . ?
C3 N1 Zn1 121.95(19) . . ?
C1 N1 Zn1 120.29(17) . . ?
C10 N2 C8 120.9(2) . . ?
C10 N2 C11 121.3(2) . . ?
C8 N2 C11 117.7(2) . . ?
N1 C1 C2 122.8(2) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C1 C2 C5 119.1(3) . . ?
C1 C2 H2 120.5 . . ?
C5 C2 H2 120.5 . . ?
N1 C3 C4 122.9(3) . . ?
N1 C3 H3 118.6 . . ?
C4 C3 H3 118.6 . . ?
C3 C4 C5 119.6(2) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C2 C5 C4 117.9(2) . . ?
C2 C5 C6 122.6(2) . . ?
C4 C5 C6 119.5(2) . . ?
C7 C6 C9 117.8(2) . . ?
C7 C6 C5 119.9(2) . . ?
C9 C6 C5 122.2(2) . . ?
C8 C7 C6 120.9(3) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
N2 C8 C7 119.9(2) . . ?
N2 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C10 C9 C6 120.1(2) . . ?
C10 C9 H9 119.9 . . ?
C6 C9 H9 119.9 . . ?
N2 C10 C9 120.0(2) . . ?
N2 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C13 122.6(2) . . ?
C12 C11 N2 116.8(2) . . ?
C13 C11 N2 120.6(2) . . ?
C11 C12 C18 118.7(2) . . ?
C11 C12 H12 120.6 . . ?
C18 C12 H12 120.6 . . ?
C11 C13 C16 118.1(2) . . ?
C11 C13 H13 120.9 . . ?
C16 C13 H13 120.9 . . ?
O3 C14 O4 125.2(2) . 1_566 ?
O3 C14 C18 117.8(2) . . ?
O4 C14 C18 117.0(2) 1_566 . ?
O2 C15 O1 123.8(2) . 1_466 ?
O2 C15 C16 119.2(2) . . ?
O1 C15 C16 117.0(2) 1_466 . ?
C17 C16 C13 119.8(2) . . ?
C17 C16 C15 119.6(2) . . ?
C13 C16 C15 120.5(2) . . ?
C18 C17 C16 120.6(2) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C12 120.1(2) . . ?
C17 C18 C14 121.8(2) . . ?
C12 C18 C14 118.1(2) . . ?
O9 N3 O8 119.1(3) . . ?
O9 N3 O7 120.4(3) . . ?
O8 N3 O7 120.4(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 Zn1 O1 C15 170.70(18) . . . 1_644 ?
N1 Zn1 O1 C15 -12.8(3) . . . 1_644 ?
O5 Zn1 O1 C15 -98.4(2) . . . 1_644 ?
O6 Zn1 O1 C15 75.5(2) . . . 1_644 ?
O1 Zn1 O4 C14 -8.8(2) . . . 1_544 ?
N1 Zn1 O4 C14 173.6(2) . . . 1_544 ?
O5 Zn1 O4 C14 -97.7(2) . . . 1_544 ?
O6 Zn1 O4 C14 82.8(2) . . . 1_544 ?
O4 Zn1 N1 C3 -179.3(2) . . . . ?
O1 Zn1 N1 C3 3.8(3) . . . . ?
O5 Zn1 N1 C3 89.2(2) . . . . ?
O6 Zn1 N1 C3 -84.1(2) . . . . ?
O4 Zn1 N1 C1 3.8(2) . . . . ?
O1 Zn1 N1 C1 -173.17(19) . . . . ?
O5 Zn1 N1 C1 -87.7(2) . . . . ?
O6 Zn1 N1 C1 99.0(2) . . . . ?
C3 N1 C1 C2 -0.9(4) . . . . ?
Zn1 N1 C1 C2 176.2(2) . . . . ?
N1 C1 C2 C5 -0.3(4) . . . . ?
C1 N1 C3 C4 1.2(5) . . . . ?
Zn1 N1 C3 C4 -175.8(2) . . . . ?
N1 C3 C4 C5 -0.3(5) . . . . ?
C1 C2 C5 C4 1.2(4) . . . . ?
C1 C2 C5 C6 179.9(3) . . . . ?
C3 C4 C5 C2 -0.9(4) . . . . ?
C3 C4 C5 C6 -179.7(3) . . . . ?
C2 C5 C6 C7 144.2(3) . . . . ?
C4 C5 C6 C7 -37.2(4) . . . . ?
C2 C5 C6 C9 -38.0(4) . . . . ?
C4 C5 C6 C9 140.7(3) . . . . ?
C9 C6 C7 C8 -3.8(4) . . . . ?
C5 C6 C7 C8 174.1(3) . . . . ?
C10 N2 C8 C7 4.9(4) . . . . ?
C11 N2 C8 C7 -170.4(3) . . . . ?
C6 C7 C8 N2 -1.3(4) . . . . ?
C7 C6 C9 C10 5.5(4) . . . . ?
C5 C6 C9 C10 -172.4(3) . . . . ?
C8 N2 C10 C9 -3.1(4) . . . . ?
C11 N2 C10 C9 172.0(3) . . . . ?
C6 C9 C10 N2 -2.2(5) . . . . ?
C10 N2 C11 C12 -135.0(3) . . . . ?
C8 N2 C11 C12 40.3(3) . . . . ?
C10 N2 C11 C13 45.2(4) . . . . ?
C8 N2 C11 C13 -139.6(3) . . . . ?
C13 C11 C12 C18 2.1(4) . . . . ?
N2 C11 C12 C18 -177.7(2) . . . . ?
C12 C11 C13 C16 -1.4(4) . . . . ?
N2 C11 C13 C16 178.4(2) . . . . ?
C11 C13 C16 C17 -0.3(4) . . . . ?
C11 C13 C16 C15 -177.9(2) . . . . ?
O2 C15 C16 C17 2.8(4) . . . . ?
O1 C15 C16 C17 -177.4(2) 1_466 . . . ?
O2 C15 C16 C13 -179.6(3) . . . . ?
O1 C15 C16 C13 0.2(4) 1_466 . . . ?
C13 C16 C17 C18 1.4(4) . . . . ?
C15 C16 C17 C18 179.0(2) . . . . ?
C16 C17 C18 C12 -0.7(4) . . . . ?
C16 C17 C18 C14 180.0(2) . . . . ?
C11 C12 C18 C17 -1.0(4) . . . . ?
C11 C12 C18 C14 178.3(2) . . . . ?
O3 C14 C18 C17 -169.8(3) . . . . ?
O4 C14 C18 C17 10.4(4) 1_566 . . . ?
O3 C14 C18 C12 10.8(4) . . . . ?
O4 C14 C18 C12 -169.0(2) 1_566 . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.108
_refine_diff_density_min         -0.686
_refine_diff_density_rms         0.102
