# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_1
_database_code_depnum_ccdc_archive 'CCDC 1479965'
_audit_update_record             
;
2016-07-20 deposited with the CCDC.
2016-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H14 N4 O9 Zn2'
_chemical_formula_weight         609.11

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'

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

_cell_length_a                   17.3383(7)
_cell_length_b                   7.7724(3)
_cell_length_c                   15.5015(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2088.99(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9825
_cell_measurement_theta_min      3.159
_cell_measurement_theta_max      27.534

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.498
_exptl_crystal_size_mid          0.392
_exptl_crystal_size_min          0.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.937
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1224
_exptl_absorpt_coefficient_mu    2.365
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3855
_exptl_absorpt_correction_T_max  0.5276
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25054
_diffrn_reflns_av_R_equivalents  0.1020
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.16
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1841
_reflns_number_gt                1763
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0572P)²+1.2317P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1841
_refine_ls_number_parameters     180
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0852
_refine_ls_wR_factor_gt          0.0838
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.071
_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
C1 C 0.82769(12) 0.6102(3) 0.71086(14) 0.0241(4) Uani 1 1 d . . .
H1 H 0.8714 0.5815 0.7424 0.029 Uiso 1 1 calc R . .
C2 C 0.75281(12) 0.6939(3) 0.60481(15) 0.0291(5) Uani 1 1 d . . .
H2 H 0.7349 0.7325 0.5517 0.035 Uiso 1 1 calc R . .
C3 C 0.71008(12) 0.6536(3) 0.67454(15) 0.0301(5) Uani 1 1 d . . .
H3 H 0.6566 0.6602 0.6773 0.036 Uiso 1 1 calc R . .
C4 C 0.89693(11) 0.6992(3) 0.57815(13) 0.0198(4) Uani 1 1 d . . .
C5 C 0.89971(11) 0.6615(3) 0.49071(13) 0.0192(4) Uani 1 1 d . . .
C6 C 0.96722(11) 0.6962(3) 0.44517(14) 0.0250(5) Uani 1 1 d . . .
H6 H 0.9699 0.6708 0.3866 0.030 Uiso 1 1 calc R . .
C7 C 1.03017(11) 0.7678(3) 0.48601(15) 0.0262(5) Uani 1 1 d . . .
H7 H 1.0754 0.7874 0.4553 0.031 Uiso 1 1 calc R . .
C8 C 1.02627(11) 0.8103(3) 0.57234(14) 0.0229(4) Uani 1 1 d . A .
C9 C 0.95970(12) 0.7752(3) 0.61880(14) 0.0240(5) Uani 1 1 d . . .
H9 H 0.9571 0.8025 0.6771 0.029 Uiso 1 1 calc R . .
C10 C 1.09265(13) 0.9026(3) 0.61407(17) 0.0282(5) Uani 1 1 d U . .
C11 C 0.83448(11) 0.5885(3) 0.43842(13) 0.0175(4) Uani 1 1 d U . .
N1 N 0.82861(10) 0.6661(3) 0.62836(11) 0.0208(4) Uani 1 1 d . . .
N2 N 0.75682(11) 0.6017(2) 0.74059(11) 0.0225(4) Uani 1 1 d . . .
O1 O 1.09250(12) 0.9346(3) 0.69201(13) 0.0517(6) Uani 1 1 d U A .
O2B O 1.147(5) 0.954(10) 0.557(3) 0.028(4) Uani 0.50(9) 1 d P A 2
O3 O 0.81176(9) 0.43852(17) 0.45081(11) 0.0252(4) Uani 1 1 d U . .
O4 O 0.80656(9) 0.6794(2) 0.37839(10) 0.0252(3) Uani 1 1 d . . .
O5 O 1.0000 1.2098(7) 0.7500 0.130(2) Uani 1 2 d SDU . .
Zn1 Zn 1.221710(13) 1.06764(3) 0.638230(15) 0.01918(15) Uani 1 1 d . . .
H5B H 1.02(15) 1.11(16) 0.7(3) 2(3) Uiso 1 1 d D . .
H5A H 1.03(11) 1.3(2) 0.750(17) 2(3) Uiso 1 1 d D . .
O2A O 1.148(5) 0.943(10) 0.573(4) 0.028(4) Uani 0.50(9) 1 d P A 1


_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 N2 1.314(3) . ?
C1 N1 1.351(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.347(3) . ?
C2 N1 1.381(3) . ?
C2 H2 0.9300 . ?
C3 N2 1.367(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(3) . ?
C4 C9 1.389(3) . ?
C4 N1 1.441(3) . ?
C5 C6 1.393(3) . ?
C5 C11 1.503(3) . ?
C6 C7 1.379(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.380(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.388(3) . ?
C8 C10 1.502(3) . ?
C9 H9 0.9300 . ?
C10 O2A 1.19(7) . ?
C10 O1 1.234(3) . ?
C10 O2B 1.35(7) . ?
C11 O3 1.246(2) . ?
C11 O4 1.265(3) . ?
C11 Zn1 2.590(2) 4_466 ?
N2 Zn1 1.9923(17) 6_557 ?
O2B Zn1 2.01(7) . ?
O3 Zn1 2.0845(16) 4_466 ?
O4 Zn1 2.0423(16) 5_776 ?
O4 Zn1 2.4328(16) 4_466 ?
O5 H5B 0.86(2) . ?
O5 H5A 0.85(2) . ?
Zn1 O2A 1.90(8) . ?
Zn1 N2 1.9923(18) 6_667 ?
Zn1 O4 2.0423(16) 5_776 ?
Zn1 O3 2.0845(16) 4_566 ?
Zn1 O4 2.4328(16) 4_566 ?
Zn1 C11 2.590(2) 4_566 ?

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
N2 C1 N1 111.05(18) . . ?
N2 C1 H1 124.5 . . ?
N1 C1 H1 124.5 . . ?
C3 C2 N1 105.96(19) . . ?
C3 C2 H2 127.0 . . ?
N1 C2 H2 127.0 . . ?
C2 C3 N2 110.1(2) . . ?
C2 C3 H3 125.0 . . ?
N2 C3 H3 125.0 . . ?
C5 C4 C9 120.37(19) . . ?
C5 C4 N1 121.24(18) . . ?
C9 C4 N1 118.36(19) . . ?
C4 C5 C6 118.90(19) . . ?
C4 C5 C11 125.49(18) . . ?
C6 C5 C11 115.60(18) . . ?
C7 C6 C5 120.7(2) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 120.20(19) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C9 119.79(19) . . ?
C7 C8 C10 119.6(2) . . ?
C9 C8 C10 120.5(2) . . ?
C8 C9 C4 120.0(2) . . ?
C8 C9 H9 120.0 . . ?
C4 C9 H9 120.0 . . ?
O2A C10 O1 118(3) . . ?
O2A C10 O2B 9(5) . . ?
O1 C10 O2B 126(3) . . ?
O2A C10 C8 121(3) . . ?
O1 C10 C8 121.1(2) . . ?
O2B C10 C8 113(3) . . ?
O3 C11 O4 121.02(19) . . ?
O3 C11 C5 120.54(18) . . ?
O4 C11 C5 118.31(18) . . ?
O3 C11 Zn1 52.65(10) . 4_466 ?
O4 C11 Zn1 68.61(11) . 4_466 ?
C5 C11 Zn1 173.02(15) . 4_466 ?
C1 N1 C2 106.82(17) . . ?
C1 N1 C4 125.36(18) . . ?
C2 N1 C4 127.72(18) . . ?
C1 N2 C3 106.08(18) . . ?
C1 N2 Zn1 128.54(15) . 6_557 ?
C3 N2 Zn1 124.36(15) . 6_557 ?
C10 O2B Zn1 100(3) . . ?
C11 O3 Zn1 98.99(13) . 4_466 ?
C11 O4 Zn1 136.25(13) . 5_776 ?
C11 O4 Zn1 82.44(12) . 4_466 ?
Zn1 O4 Zn1 126.96(7) 5_776 4_466 ?
H5B O5 H5A 111(5) . . ?
O2A Zn1 N2 140.9(17) . 6_667 ?
O2A Zn1 O2B 7(3) . . ?
N2 Zn1 O2B 147.8(17) 6_667 . ?
O2A Zn1 O4 105(2) . 5_776 ?
N2 Zn1 O4 93.69(7) 6_667 5_776 ?
O2B Zn1 O4 101(2) . 5_776 ?
O2A Zn1 O3 98(2) . 4_566 ?
N2 Zn1 O3 113.49(7) 6_667 4_566 ?
O2B Zn1 O3 93(2) . 4_566 ?
O4 Zn1 O3 96.80(6) 5_776 4_566 ?
O2A Zn1 O4 87(2) . 4_566 ?
N2 Zn1 O4 91.14(7) 6_667 4_566 ?
O2B Zn1 O4 89(2) . 4_566 ?
O4 Zn1 O4 153.07(5) 5_776 4_566 ?
O3 Zn1 O4 57.24(5) 4_566 4_566 ?
O2A Zn1 C11 92(2) . 4_566 ?
N2 Zn1 C11 105.32(7) 6_667 4_566 ?
O2B Zn1 C11 90(2) . 4_566 ?
O4 Zn1 C11 125.06(7) 5_776 4_566 ?
O3 Zn1 C11 28.36(6) 4_566 4_566 ?
O4 Zn1 C11 28.95(6) 4_566 4_566 ?
C10 O2A Zn1 113(4) . . ?

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
N1 C2 C3 N2 0.0(3) . . . . ?
C9 C4 C5 C6 2.0(3) . . . . ?
N1 C4 C5 C6 179.96(18) . . . . ?
C9 C4 C5 C11 -176.5(2) . . . . ?
N1 C4 C5 C11 1.5(3) . . . . ?
C4 C5 C6 C7 -0.4(3) . . . . ?
C11 C5 C6 C7 178.23(19) . . . . ?
C5 C6 C7 C8 -1.8(3) . . . . ?
C6 C7 C8 C9 2.3(3) . . . . ?
C6 C7 C8 C10 -174.5(2) . . . . ?
C7 C8 C9 C4 -0.7(3) . . . . ?
C10 C8 C9 C4 176.1(2) . . . . ?
C5 C4 C9 C8 -1.4(3) . . . . ?
N1 C4 C9 C8 -179.48(19) . . . . ?
C7 C8 C10 O2A 2(4) . . . . ?
C9 C8 C10 O2A -175(4) . . . . ?
C7 C8 C10 O1 -176.3(2) . . . . ?
C9 C8 C10 O1 6.8(3) . . . . ?
C7 C8 C10 O2B 8(4) . . . . ?
C9 C8 C10 O2B -169(4) . . . . ?
C4 C5 C11 O3 -68.3(3) . . . . ?
C6 C5 C11 O3 113.2(2) . . . . ?
C4 C5 C11 O4 115.8(2) . . . . ?
C6 C5 C11 O4 -62.7(3) . . . . ?
C4 C5 C11 Zn1 -56.0(12) . . . 4_466 ?
C6 C5 C11 Zn1 125.5(11) . . . 4_466 ?
N2 C1 N1 C2 -0.2(3) . . . . ?
N2 C1 N1 C4 176.3(2) . . . . ?
C3 C2 N1 C1 0.2(3) . . . . ?
C3 C2 N1 C4 -176.3(2) . . . . ?
C5 C4 N1 C1 143.0(2) . . . . ?
C9 C4 N1 C1 -38.9(3) . . . . ?
C5 C4 N1 C2 -41.1(3) . . . . ?
C9 C4 N1 C2 136.9(2) . . . . ?
N1 C1 N2 C3 0.2(3) . . . . ?
N1 C1 N2 Zn1 -168.46(15) . . . 6_557 ?
C2 C3 N2 C1 -0.1(3) . . . . ?
C2 C3 N2 Zn1 169.17(17) . . . 6_557 ?
O2A C10 O2B Zn1 -36(42) . . . . ?
O1 C10 O2B Zn1 5(5) . . . . ?
C8 C10 O2B Zn1 179.9(14) . . . . ?
O4 C11 O3 Zn1 -6.1(2) . . . 4_466 ?
C5 C11 O3 Zn1 178.13(15) . . . 4_466 ?
O3 C11 O4 Zn1 142.84(17) . . . 5_776 ?
C5 C11 O4 Zn1 -41.3(3) . . . 5_776 ?
Zn1 C11 O4 Zn1 137.61(19) 4_466 . . 5_776 ?
O3 C11 O4 Zn1 5.23(18) . . . 4_466 ?
C5 C11 O4 Zn1 -178.94(17) . . . 4_466 ?
C10 O2B Zn1 O2A 29(35) . . . . ?
C10 O2B Zn1 N2 15(7) . . . 6_667 ?
C10 O2B Zn1 O4 -100(3) . . . 5_776 ?
C10 O2B Zn1 O3 162(4) . . . 4_566 ?
C10 O2B Zn1 O4 105(4) . . . 4_566 ?
C10 O2B Zn1 C11 134(4) . . . 4_566 ?
O1 C10 O2A Zn1 -5(6) . . . . ?
O2B C10 O2A Zn1 138(47) . . . . ?
C8 C10 O2A Zn1 177.1(18) . . . . ?
N2 Zn1 O2A C10 24(8) 6_667 . . . ?
O2B Zn1 O2A C10 -143(43) . . . . ?
O4 Zn1 O2A C10 -92(4) 5_776 . . . ?
O3 Zn1 O2A C10 169(4) 4_566 . . . ?
O4 Zn1 O2A C10 113(5) 4_566 . . . ?
C11 Zn1 O2A C10 141(5) 4_566 . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.087
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1479967'
_audit_update_record             
;
2016-07-20 deposited with the CCDC.
2016-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H28 N8 O11 Zn2'
_chemical_formula_weight         855.38

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   P2/n

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

_cell_length_a                   15.2246(8)
_cell_length_b                   7.3657(4)
_cell_length_c                   16.7773(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.831(2)
_cell_angle_gamma                90.00
_cell_volume                     1800.81(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8526
_cell_measurement_theta_min      3.043
_cell_measurement_theta_max      23.393

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.157
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.093
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    1.404
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8097
_exptl_absorpt_correction_T_max  0.8805
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            30952
_diffrn_reflns_av_R_equivalents  0.0811
_diffrn_reflns_av_sigmaI/netI    0.0414
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3168
_reflns_number_gt                2433
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0765P)²+0.9332P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3168
_refine_ls_number_parameters     255
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1245
_refine_ls_wR_factor_gt          0.1152
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.057
_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
C1 C 0.9238(4) 1.1364(6) 0.3616(3) 0.0596(13) Uani 1 1 d U . .
H1 H 0.9346 1.2607 0.3663 0.072 Uiso 1 1 calc R . .
C2 C 0.8770(3) 0.8782(5) 0.3802(2) 0.0375(9) Uani 1 1 d . . .
H2 H 0.8502 0.7798 0.3990 0.045 Uiso 1 1 calc R . .
C4 C 0.9381(3) 0.7136(5) 0.2792(2) 0.0346(9) Uani 1 1 d . . .
C5 C 1.0251(3) 0.6398(5) 0.2934(2) 0.0332(9) Uani 1 1 d . . .
C6 C 1.0340(3) 0.4942(6) 0.2446(2) 0.0398(10) Uani 1 1 d . . .
H6 H 1.0920 0.4453 0.2509 0.048 Uiso 1 1 calc R . .
C7 C 0.9597(3) 0.4193(6) 0.1868(2) 0.0406(10) Uani 1 1 d . . .
H7 H 0.9678 0.3198 0.1555 0.049 Uiso 1 1 calc R . .
C8 C 0.8733(3) 0.4908(5) 0.1750(2) 0.0354(9) Uani 1 1 d . . .
C10 C 0.8634(3) 0.6422(6) 0.2205(2) 0.0396(10) Uani 1 1 d . . .
H10 H 0.8060 0.6958 0.2114 0.047 Uiso 1 1 calc R . .
C9 C 0.7894(3) 0.4101(6) 0.1146(3) 0.0425(10) Uani 1 1 d . . .
C11 C 1.1068(3) 0.7074(5) 0.3610(3) 0.0378(10) Uani 1 1 d . . .
C12 C 0.7958(3) 0.8213(6) 0.5919(3) 0.0561(13) Uani 1 1 d . . .
H12 H 0.8550 0.8368 0.6269 0.067 Uiso 1 1 calc R . .
C13 C 0.7370(3) 0.6916(6) 0.5997(3) 0.0548(13) Uani 1 1 d . . .
H13 H 0.7476 0.6025 0.6407 0.066 Uiso 1 1 calc R . .
C14 C 0.6728(3) 0.8601(5) 0.4924(3) 0.0395(10) Uani 1 1 d . . .
H14 H 0.6299 0.9067 0.4456 0.047 Uiso 1 1 calc R . .
C15 C 0.5774(3) 0.6059(5) 0.5178(2) 0.0355(9) Uani 1 1 d . . .
C17 C 0.5843(3) 0.4254(6) 0.5397(2) 0.0392(9) Uani 1 1 d . . .
H17 H 0.6414 0.3756 0.5666 0.047 Uiso 1 1 calc R . .
C16 C 0.4932(3) 0.6819(5) 0.4780(3) 0.0395(10) Uani 1 1 d . . .
H16 H 0.4888 0.8041 0.4633 0.047 Uiso 1 1 calc R . .
N1 N 0.8750(2) 1.0484(4) 0.4054(2) 0.0394(8) Uani 1 1 d . . .
N2 N 0.9226(2) 0.8698(4) 0.3244(2) 0.0376(8) Uani 1 1 d . . .
N3 N 0.7551(2) 0.9267(5) 0.5246(2) 0.0399(8) Uani 1 1 d . . .
N4 N 0.6584(2) 0.7159(4) 0.5358(2) 0.0368(8) Uani 1 1 d . . .
C3 C 0.9541(3) 1.0346(5) 0.3127(3) 0.0414(10) Uani 1 1 d U . .
H3 H 0.9892 1.0675 0.2780 0.050 Uiso 1 1 calc RD . .
O1 O 0.7139(2) 0.4828(5) 0.1027(2) 0.0691(10) Uani 1 1 d . . .
O2 O 0.80250(19) 0.2632(4) 0.08061(18) 0.0493(8) Uani 1 1 d . . .
O3 O 1.09027(19) 0.7585(4) 0.42711(17) 0.0475(7) Uani 1 1 d . . .
O4 O 1.1838(2) 0.7047(5) 0.3509(2) 0.0568(8) Uani 1 1 d . . .
Zn1 Zn 0.80803(3) 1.14766(6) 0.48505(3) 0.03184(19) Uani 1 1 d . . .
O5 O 1.0569(6) 1.0268(10) 0.1669(4) 0.182(3) Uani 1 1 d GU . .
H5A H 1.0762 1.1214 0.1957 0.273 Uiso 1 1 d GD . .
H5B H 1.1004 0.9504 0.1742 0.273 Uiso 1 1 d G . .
O6 O 1.2500 0.9150(15) 0.2500 0.209(5) Uani 1 2 d SGU . .
H6A H 1.2558 0.8096 0.2315 0.313 Uiso 0.50 1 d PG . .
H6B H 1.2187 0.9082 0.2844 0.313 Uiso 0.50 1 d PG . .


_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 C3 1.291(6) . ?
C1 N1 1.351(5) . ?
C1 H1 0.9300 . ?
C2 N2 1.318(5) . ?
C2 N1 1.326(5) . ?
C2 H2 0.9300 . ?
C4 C10 1.375(5) . ?
C4 C5 1.387(5) . ?
C4 N2 1.436(5) . ?
C5 C6 1.380(5) . ?
C5 C11 1.505(5) . ?
C6 C7 1.375(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.376(5) . ?
C7 H7 0.9300 . ?
C8 C10 1.384(5) . ?
C8 C9 1.505(5) . ?
C10 H10 0.9300 . ?
C9 O1 1.230(5) . ?
C9 O2 1.266(5) . ?
C11 O4 1.232(5) . ?
C11 O3 1.263(5) . ?
C12 C13 1.342(6) . ?
C12 N3 1.362(5) . ?
C12 H12 0.9300 . ?
C13 N4 1.367(5) . ?
C13 H13 0.9300 . ?
C14 N3 1.308(5) . ?
C14 N4 1.341(5) . ?
C14 H14 0.9300 . ?
C15 C17 1.375(6) . ?
C15 C16 1.382(6) . ?
C15 N4 1.433(5) . ?
C17 C16 1.379(6) 3_666 ?
C17 H17 0.9300 . ?
C16 C17 1.379(6) 3_666 ?
C16 H16 0.9300 . ?
N1 Zn1 2.038(3) . ?
N2 C3 1.340(5) . ?
N3 Zn1 2.012(3) . ?
C3 H3 0.9300 . ?
O2 Zn1 1.922(3) 2_645 ?
O3 Zn1 1.930(3) 3_776 ?
Zn1 O2 1.922(3) 2_665 ?
Zn1 O3 1.930(3) 3_776 ?
O5 H5A 0.8499 . ?
O5 H5B 0.8500 . ?
O6 H6A 0.8500 . ?
O6 H6B 0.8499 . ?

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
C3 C1 N1 114.9(4) . . ?
C3 C1 H1 122.6 . . ?
N1 C1 H1 122.6 . . ?
N2 C2 N1 109.6(4) . . ?
N2 C2 H2 125.2 . . ?
N1 C2 H2 125.2 . . ?
C10 C4 C5 121.6(4) . . ?
C10 C4 N2 117.2(3) . . ?
C5 C4 N2 121.2(3) . . ?
C6 C5 C4 117.1(3) . . ?
C6 C5 C11 120.2(3) . . ?
C4 C5 C11 122.7(3) . . ?
C7 C6 C5 121.9(4) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C6 C7 C8 120.4(4) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C10 118.7(4) . . ?
C7 C8 C9 122.4(4) . . ?
C10 C8 C9 118.9(4) . . ?
C4 C10 C8 120.2(4) . . ?
C4 C10 H10 119.9 . . ?
C8 C10 H10 119.9 . . ?
O1 C9 O2 124.1(4) . . ?
O1 C9 C8 120.6(4) . . ?
O2 C9 C8 115.3(4) . . ?
O4 C11 O3 124.4(4) . . ?
O4 C11 C5 120.1(4) . . ?
O3 C11 C5 115.4(3) . . ?
C13 C12 N3 109.3(4) . . ?
C13 C12 H12 125.3 . . ?
N3 C12 H12 125.3 . . ?
C12 C13 N4 106.7(4) . . ?
C12 C13 H13 126.6 . . ?
N4 C13 H13 126.6 . . ?
N3 C14 N4 111.2(4) . . ?
N3 C14 H14 124.4 . . ?
N4 C14 H14 124.4 . . ?
C17 C15 C16 120.7(4) . . ?
C17 C15 N4 119.7(4) . . ?
C16 C15 N4 119.6(4) . . ?
C15 C17 C16 120.1(4) . 3_666 ?
C15 C17 H17 119.9 . . ?
C16 C17 H17 119.9 3_666 . ?
C17 C16 C15 119.2(4) 3_666 . ?
C17 C16 H16 120.4 3_666 . ?
C15 C16 H16 120.4 . . ?
C2 N1 C1 102.3(4) . . ?
C2 N1 Zn1 127.6(3) . . ?
C1 N1 Zn1 130.0(3) . . ?
C2 N2 C3 110.2(3) . . ?
C2 N2 C4 127.9(3) . . ?
C3 N2 C4 121.9(3) . . ?
C14 N3 C12 106.2(3) . . ?
C14 N3 Zn1 126.5(3) . . ?
C12 N3 Zn1 127.2(3) . . ?
C14 N4 C13 106.6(3) . . ?
C14 N4 C15 126.9(3) . . ?
C13 N4 C15 126.5(3) . . ?
C1 C3 N2 102.9(3) . . ?
C1 C3 H3 128.5 . . ?
N2 C3 H3 128.5 . . ?
C9 O2 Zn1 114.2(3) . 2_645 ?
C11 O3 Zn1 117.2(3) . 3_776 ?
O2 Zn1 O3 130.90(15) 2_665 3_776 ?
O2 Zn1 N3 100.33(13) 2_665 . ?
O3 Zn1 N3 110.32(13) 3_776 . ?
O2 Zn1 N1 107.72(13) 2_665 . ?
O3 Zn1 N1 100.72(13) 3_776 . ?
N3 Zn1 N1 104.49(13) . . ?
H5A O5 H5B 109.5 . . ?
H6A O6 H6B 109.5 . . ?

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
C10 C4 C5 C6 1.6(6) . . . . ?
N2 C4 C5 C6 -177.4(3) . . . . ?
C10 C4 C5 C11 -175.8(4) . . . . ?
N2 C4 C5 C11 5.1(6) . . . . ?
C4 C5 C6 C7 -2.9(6) . . . . ?
C11 C5 C6 C7 174.6(4) . . . . ?
C5 C6 C7 C8 1.1(6) . . . . ?
C6 C7 C8 C10 1.9(6) . . . . ?
C6 C7 C8 C9 -178.0(4) . . . . ?
C5 C4 C10 C8 1.4(6) . . . . ?
N2 C4 C10 C8 -179.6(4) . . . . ?
C7 C8 C10 C4 -3.1(6) . . . . ?
C9 C8 C10 C4 176.7(4) . . . . ?
C7 C8 C9 O1 -176.4(4) . . . . ?
C10 C8 C9 O1 3.7(6) . . . . ?
C7 C8 C9 O2 5.7(6) . . . . ?
C10 C8 C9 O2 -174.1(4) . . . . ?
C6 C5 C11 O4 35.6(6) . . . . ?
C4 C5 C11 O4 -147.0(4) . . . . ?
C6 C5 C11 O3 -142.0(4) . . . . ?
C4 C5 C11 O3 35.3(5) . . . . ?
N3 C12 C13 N4 0.4(6) . . . . ?
C16 C15 C17 C16 0.1(7) . . . 3_666 ?
N4 C15 C17 C16 -179.4(4) . . . 3_666 ?
C17 C15 C16 C17 -0.1(7) . . . 3_666 ?
N4 C15 C16 C17 179.4(4) . . . 3_666 ?
N2 C2 N1 C1 -1.0(5) . . . . ?
N2 C2 N1 Zn1 175.8(3) . . . . ?
C3 C1 N1 C2 0.2(6) . . . . ?
C3 C1 N1 Zn1 -176.5(3) . . . . ?
N1 C2 N2 C3 1.5(5) . . . . ?
N1 C2 N2 C4 -177.5(4) . . . . ?
C10 C4 N2 C2 69.0(5) . . . . ?
C5 C4 N2 C2 -111.9(5) . . . . ?
C10 C4 N2 C3 -109.9(4) . . . . ?
C5 C4 N2 C3 69.2(5) . . . . ?
N4 C14 N3 C12 -0.2(5) . . . . ?
N4 C14 N3 Zn1 -177.6(3) . . . . ?
C13 C12 N3 C14 -0.1(6) . . . . ?
C13 C12 N3 Zn1 177.2(3) . . . . ?
N3 C14 N4 C13 0.4(5) . . . . ?
N3 C14 N4 C15 -178.3(4) . . . . ?
C12 C13 N4 C14 -0.5(5) . . . . ?
C12 C13 N4 C15 178.2(4) . . . . ?
C17 C15 N4 C14 150.0(4) . . . . ?
C16 C15 N4 C14 -29.5(6) . . . . ?
C17 C15 N4 C13 -28.5(6) . . . . ?
C16 C15 N4 C13 152.0(4) . . . . ?
N1 C1 C3 N2 0.7(6) . . . . ?
C2 N2 C3 C1 -1.3(5) . . . . ?
C4 N2 C3 C1 177.8(4) . . . . ?
O1 C9 O2 Zn1 -5.3(6) . . . 2_645 ?
C8 C9 O2 Zn1 172.5(3) . . . 2_645 ?
O4 C11 O3 Zn1 4.0(6) . . . 3_776 ?
C5 C11 O3 Zn1 -178.5(2) . . . 3_776 ?
C14 N3 Zn1 O2 18.0(4) . . . 2_665 ?
C12 N3 Zn1 O2 -158.9(4) . . . 2_665 ?
C14 N3 Zn1 O3 158.9(3) . . . 3_776 ?
C12 N3 Zn1 O3 -17.9(4) . . . 3_776 ?
C14 N3 Zn1 N1 -93.6(4) . . . . ?
C12 N3 Zn1 N1 89.6(4) . . . . ?
C2 N1 Zn1 O2 -101.2(3) . . . 2_665 ?
C1 N1 Zn1 O2 74.7(4) . . . 2_665 ?
C2 N1 Zn1 O3 119.3(3) . . . 3_776 ?
C1 N1 Zn1 O3 -64.7(4) . . . 3_776 ?
C2 N1 Zn1 N3 4.9(4) . . . . ?
C1 N1 Zn1 N3 -179.2(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.276
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.086
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1479968'
_audit_update_record             
;
2016-07-20 deposited with the CCDC.
2016-08-17 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 H19 N4 Ni O8'
_chemical_formula_weight         466.07

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'
Ni Ni 0.3393 1.1124 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   7.3222(3)
_cell_length_b                   25.5967(10)
_cell_length_c                   10.3654(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.3200(10)
_cell_angle_gamma                90.00
_cell_volume                     1917.08(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9523
_cell_measurement_theta_min      3.109
_cell_measurement_theta_max      27.484

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.498
_exptl_crystal_size_mid          0.465
_exptl_crystal_size_min          0.401
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             964
_exptl_absorpt_coefficient_mu    1.067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7832
_exptl_absorpt_correction_T_max  0.9721
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24801
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_av_sigmaI/netI    0.0190
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3374
_reflns_number_gt                3190
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0377P)²+1.8005P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3374
_refine_ls_number_parameters     295
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_ref         0.0785
_refine_ls_wR_factor_gt          0.0773
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.002
_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
C1 C 0.5111(3) 0.79527(9) 0.4946(2) 0.0349(5) Uani 1 1 d . . .
H1 H 0.5909 0.8221 0.5273 0.042 Uiso 1 1 calc R . .
C2 C 0.5581(3) 0.74450(9) 0.4917(2) 0.0365(5) Uani 1 1 d . . .
H2 H 0.6735 0.7299 0.5215 0.044 Uiso 1 1 calc R . .
C3 C 0.2667(3) 0.75455(8) 0.4082(2) 0.0296(5) Uani 1 1 d . . .
H3 H 0.1457 0.7471 0.3699 0.036 Uiso 1 1 calc R . .
C4 C 0.3827(3) 0.66311(8) 0.42065(19) 0.0254(4) Uani 1 1 d . . .
C5 C 0.3357(3) 0.64198(8) 0.2971(2) 0.0265(4) Uani 1 1 d . . .
H5 H 0.3097 0.6638 0.2247 0.032 Uiso 1 1 calc R . .
C6 C 0.3274(3) 0.58792(8) 0.2814(2) 0.0275(4) Uani 1 1 d . . .
C7 C 0.3736(3) 0.55636(8) 0.3907(2) 0.0356(5) Uani 1 1 d . . .
H7 H 0.3715 0.5202 0.3810 0.043 Uiso 1 1 calc R . .
C8 C 0.4226(3) 0.57780(9) 0.5133(2) 0.0370(5) Uani 1 1 d . . .
H8 H 0.4551 0.5560 0.5851 0.044 Uiso 1 1 calc R . .
C9 C 0.4239(3) 0.63173(8) 0.5311(2) 0.0283(5) Uani 1 1 d . . .
C10 C 0.4638(3) 0.65278(9) 0.6685(2) 0.0311(5) Uani 1 1 d . . .
C11 C 0.2714(3) 0.56381(8) 0.1485(2) 0.0307(5) Uani 1 1 d . . .
C12 C 0.2816(3) 0.84656(9) 0.7286(2) 0.0383(5) Uani 1 1 d . . .
H12 H 0.2594 0.8110 0.7169 0.046 Uiso 1 1 calc R . .
C13 C 0.3445(4) 0.86965(9) 0.8439(2) 0.0387(6) Uani 1 1 d . . .
H13 H 0.3738 0.8533 0.9247 0.046 Uiso 1 1 calc R . .
C14 C 0.3014(3) 0.92831(9) 0.6884(2) 0.0357(5) Uani 1 1 d . . .
H14 H 0.2967 0.9603 0.6453 0.043 Uiso 1 1 calc R . .
C15 C 0.4264(3) 0.96214(9) 0.9110(2) 0.0329(5) Uani 1 1 d . . .
C16 C 0.4574(4) 0.95113(10) 1.0429(2) 0.0428(6) Uani 1 1 d . . .
H16 H 0.4281 0.9184 1.0725 0.051 Uiso 1 1 calc R . .
C17 C 0.4677(4) 1.01095(10) 0.8687(2) 0.0434(6) Uani 1 1 d . . .
H17 H 0.4453 1.0186 0.7798 0.052 Uiso 1 1 calc R . .
N1 N 0.3284(2) 0.80158(7) 0.44216(16) 0.0272(4) Uani 1 1 d . . .
N2 N 0.4004(2) 0.71868(6) 0.43573(16) 0.0263(4) Uani 1 1 d . . .
N3 N 0.2549(3) 0.88344(7) 0.63052(17) 0.0325(4) Uani 1 1 d . . .
N4 N 0.3568(3) 0.92221(7) 0.81857(17) 0.0321(4) Uani 1 1 d . . .
Ni1 Ni 0.18030(3) 0.869303(9) 0.43210(2) 0.02411(10) Uani 1 1 d . . .
O1 O 0.2647(3) 0.51505(6) 0.14098(19) 0.0528(5) Uani 1 1 d . . .
O2 O 0.2341(2) 0.59354(6) 0.05137(15) 0.0356(4) Uani 1 1 d . . .
O3 O 0.6132(2) 0.63735(7) 0.73407(15) 0.0389(4) Uani 1 1 d . . .
O4 O 0.3484(2) 0.68183(8) 0.70723(16) 0.0480(5) Uani 1 1 d . . .
O5 O -0.0511(2) 0.82781(6) 0.46508(15) 0.0334(3) Uani 1 1 d D . .
O6 O 0.0102(3) 0.93686(7) 0.4053(2) 0.0586(5) Uani 1 1 d D . .
O7 O 0.3993(2) 0.91610(6) 0.38950(16) 0.0352(4) Uani 1 1 d D . .
O8 O -0.0481(4) 0.68234(12) 0.6317(2) 0.0809(7) Uani 1 1 d D . .
H8A H -0.004(5) 0.7110(6) 0.619(3) 0.080 Uiso 1 1 d D . .
H6A H -0.076(3) 0.9384(10) 0.447(3) 0.080 Uiso 1 1 d D . .
H7A H 0.360(3) 0.9459(4) 0.375(3) 0.080 Uiso 1 1 d D . .
H7B H 0.500(2) 0.9142(10) 0.437(3) 0.080 Uiso 1 1 d D . .
H5A H -0.117(3) 0.8466(11) 0.502(2) 0.080 Uiso 1 1 d D . .
H5B H -0.095(4) 0.8200(13) 0.3898(12) 0.080 Uiso 1 1 d D . .
H6B H 0.059(4) 0.9650(5) 0.395(3) 0.080 Uiso 1 1 d D . .
H8B H -0.080(5) 0.6788(11) 0.7036(16) 0.080 Uiso 1 1 d 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
C1 C2 1.346(3) . ?
C1 N1 1.370(3) . ?
C1 H1 0.9300 . ?
C2 N2 1.374(3) . ?
C2 H2 0.9300 . ?
C3 N1 1.314(3) . ?
C3 N2 1.339(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(3) . ?
C4 C9 1.391(3) . ?
C4 N2 1.434(3) . ?
C5 C6 1.393(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.388(3) . ?
C6 C11 1.505(3) . ?
C7 C8 1.378(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.393(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.506(3) . ?
C10 O4 1.240(3) . ?
C10 O3 1.255(3) . ?
C11 O1 1.251(3) . ?
C11 O2 1.256(3) . ?
C12 C13 1.345(3) . ?
C12 N3 1.378(3) . ?
C12 H12 0.9300 . ?
C13 N4 1.376(3) . ?
C13 H13 0.9300 . ?
C14 N3 1.315(3) . ?
C14 N4 1.353(3) . ?
C14 H14 0.9300 . ?
C15 C17 1.374(3) . ?
C15 C16 1.379(3) . ?
C15 N4 1.436(3) . ?
C16 C17 1.385(3) 3_677 ?
C16 H16 0.9300 . ?
C17 C16 1.385(3) 3_677 ?
C17 H17 0.9300 . ?
N1 Ni1 2.0382(17) . ?
N3 Ni1 2.0726(17) . ?
Ni1 O3 2.0389(15) 4_575 ?
Ni1 O5 2.0746(15) . ?
Ni1 O7 2.1051(16) . ?
Ni1 O6 2.1228(18) . ?
O3 Ni1 2.0389(15) 4_676 ?
O5 H5A 0.8200(11) . ?
O5 H5B 0.8201(11) . ?
O6 H6A 0.8200(11) . ?
O6 H6B 0.8200(11) . ?
O7 H7A 0.8200(10) . ?
O7 H7B 0.8200(11) . ?
O8 H8A 0.8203(11) . ?
O8 H8B 0.8200(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
C2 C1 N1 110.00(19) . . ?
C2 C1 H1 125.0 . . ?
N1 C1 H1 125.0 . . ?
C1 C2 N2 105.87(19) . . ?
C1 C2 H2 127.1 . . ?
N2 C2 H2 127.1 . . ?
N1 C3 N2 111.32(18) . . ?
N1 C3 H3 124.3 . . ?
N2 C3 H3 124.3 . . ?
C5 C4 C9 121.68(19) . . ?
C5 C4 N2 119.60(18) . . ?
C9 C4 N2 118.62(18) . . ?
C4 C5 C6 119.81(19) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C7 C6 C5 118.82(19) . . ?
C7 C6 C11 120.19(19) . . ?
C5 C6 C11 120.99(19) . . ?
C8 C7 C6 120.9(2) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 120.8(2) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C4 C9 C8 117.9(2) . . ?
C4 C9 C10 123.68(19) . . ?
C8 C9 C10 118.43(19) . . ?
O4 C10 O3 126.4(2) . . ?
O4 C10 C9 118.85(18) . . ?
O3 C10 C9 114.72(19) . . ?
O1 C11 O2 123.6(2) . . ?
O1 C11 C6 117.9(2) . . ?
O2 C11 C6 118.47(18) . . ?
C13 C12 N3 110.0(2) . . ?
C13 C12 H12 125.0 . . ?
N3 C12 H12 125.0 . . ?
C12 C13 N4 106.5(2) . . ?
C12 C13 H13 126.8 . . ?
N4 C13 H13 126.8 . . ?
N3 C14 N4 111.6(2) . . ?
N3 C14 H14 124.2 . . ?
N4 C14 H14 124.2 . . ?
C17 C15 C16 119.5(2) . . ?
C17 C15 N4 120.5(2) . . ?
C16 C15 N4 120.0(2) . . ?
C15 C16 C17 119.8(2) . 3_677 ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 3_677 . ?
C15 C17 C16 120.7(2) . 3_677 ?
C15 C17 H17 119.7 . . ?
C16 C17 H17 119.7 3_677 . ?
C3 N1 C1 105.63(17) . . ?
C3 N1 Ni1 127.50(14) . . ?
C1 N1 Ni1 126.73(14) . . ?
C3 N2 C2 107.18(17) . . ?
C3 N2 C4 127.33(17) . . ?
C2 N2 C4 125.31(17) . . ?
C14 N3 C12 105.43(18) . . ?
C14 N3 Ni1 127.79(16) . . ?
C12 N3 Ni1 126.57(15) . . ?
C14 N4 C13 106.52(18) . . ?
C14 N4 C15 126.8(2) . . ?
C13 N4 C15 126.56(19) . . ?
N1 Ni1 O3 91.14(7) . 4_575 ?
N1 Ni1 N3 92.58(7) . . ?
O3 Ni1 N3 174.52(7) 4_575 . ?
N1 Ni1 O5 89.89(7) . . ?
O3 Ni1 O5 93.04(6) 4_575 . ?
N3 Ni1 O5 90.98(7) . . ?
N1 Ni1 O7 94.45(7) . . ?
O3 Ni1 O7 84.48(6) 4_575 . ?
N3 Ni1 O7 91.22(7) . . ?
O5 Ni1 O7 175.03(6) . . ?
N1 Ni1 O6 174.50(8) . . ?
O3 Ni1 O6 84.02(8) 4_575 . ?
N3 Ni1 O6 92.43(9) . . ?
O5 Ni1 O6 87.76(7) . . ?
O7 Ni1 O6 87.69(7) . . ?
C10 O3 Ni1 128.20(15) . 4_676 ?
Ni1 O5 H5A 110(2) . . ?
Ni1 O5 H5B 100(2) . . ?
H5A O5 H5B 114.6(2) . . ?
Ni1 O6 H6A 117(2) . . ?
Ni1 O6 H6B 118(2) . . ?
H6A O6 H6B 114.6(2) . . ?
Ni1 O7 H7A 108(2) . . ?
Ni1 O7 H7B 119(2) . . ?
H7A O7 H7B 114.6(2) . . ?
H8A O8 H8B 114.6(2) . . ?

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
N1 C1 C2 N2 0.2(3) . . . . ?
C9 C4 C5 C6 0.5(3) . . . . ?
N2 C4 C5 C6 176.77(19) . . . . ?
C4 C5 C6 C7 -2.4(3) . . . . ?
C4 C5 C6 C11 178.23(19) . . . . ?
C5 C6 C7 C8 1.6(3) . . . . ?
C11 C6 C7 C8 -179.0(2) . . . . ?
C6 C7 C8 C9 1.1(4) . . . . ?
C5 C4 C9 C8 2.1(3) . . . . ?
N2 C4 C9 C8 -174.2(2) . . . . ?
C5 C4 C9 C10 -175.91(19) . . . . ?
N2 C4 C9 C10 7.8(3) . . . . ?
C7 C8 C9 C4 -2.9(3) . . . . ?
C7 C8 C9 C10 175.2(2) . . . . ?
C4 C9 C10 O4 55.2(3) . . . . ?
C8 C9 C10 O4 -122.8(2) . . . . ?
C4 C9 C10 O3 -126.5(2) . . . . ?
C8 C9 C10 O3 55.5(3) . . . . ?
C7 C6 C11 O1 1.3(3) . . . . ?
C5 C6 C11 O1 -179.3(2) . . . . ?
C7 C6 C11 O2 -178.6(2) . . . . ?
C5 C6 C11 O2 0.8(3) . . . . ?
N3 C12 C13 N4 0.4(3) . . . . ?
C17 C15 C16 C17 -0.9(4) . . . 3_677 ?
N4 C15 C16 C17 177.1(2) . . . 3_677 ?
C16 C15 C17 C16 0.9(4) . . . 3_677 ?
N4 C15 C17 C16 -177.1(2) . . . 3_677 ?
N2 C3 N1 C1 -0.2(2) . . . . ?
N2 C3 N1 Ni1 -176.09(14) . . . . ?
C2 C1 N1 C3 0.0(3) . . . . ?
C2 C1 N1 Ni1 175.95(16) . . . . ?
N1 C3 N2 C2 0.3(3) . . . . ?
N1 C3 N2 C4 175.61(19) . . . . ?
C1 C2 N2 C3 -0.3(3) . . . . ?
C1 C2 N2 C4 -175.7(2) . . . . ?
C5 C4 N2 C3 65.0(3) . . . . ?
C9 C4 N2 C3 -118.7(2) . . . . ?
C5 C4 N2 C2 -120.5(2) . . . . ?
C9 C4 N2 C2 55.8(3) . . . . ?
N4 C14 N3 C12 0.1(3) . . . . ?
N4 C14 N3 Ni1 -174.83(15) . . . . ?
C13 C12 N3 C14 -0.3(3) . . . . ?
C13 C12 N3 Ni1 174.71(17) . . . . ?
N3 C14 N4 C13 0.1(3) . . . . ?
N3 C14 N4 C15 176.4(2) . . . . ?
C12 C13 N4 C14 -0.3(3) . . . . ?
C12 C13 N4 C15 -176.6(2) . . . . ?
C17 C15 N4 C14 -9.5(4) . . . . ?
C16 C15 N4 C14 172.5(2) . . . . ?
C17 C15 N4 C13 166.1(2) . . . . ?
C16 C15 N4 C13 -11.9(4) . . . . ?
C3 N1 Ni1 O3 -61.79(19) . . . 4_575 ?
C1 N1 Ni1 O3 123.15(18) . . . 4_575 ?
C3 N1 Ni1 N3 122.23(19) . . . . ?
C1 N1 Ni1 N3 -52.83(19) . . . . ?
C3 N1 Ni1 O5 31.25(19) . . . . ?
C1 N1 Ni1 O5 -143.80(18) . . . . ?
C3 N1 Ni1 O7 -146.34(18) . . . . ?
C1 N1 Ni1 O7 38.60(19) . . . . ?
C3 N1 Ni1 O6 -33.5(8) . . . . ?
C1 N1 Ni1 O6 151.4(7) . . . . ?
C14 N3 Ni1 N1 139.0(2) . . . . ?
C12 N3 Ni1 N1 -34.9(2) . . . . ?
C14 N3 Ni1 O3 6.2(8) . . . 4_575 ?
C12 N3 Ni1 O3 -167.7(7) . . . 4_575 ?
C14 N3 Ni1 O5 -131.1(2) . . . . ?
C12 N3 Ni1 O5 55.00(19) . . . . ?
C14 N3 Ni1 O7 44.5(2) . . . . ?
C12 N3 Ni1 O7 -129.45(19) . . . . ?
C14 N3 Ni1 O6 -43.3(2) . . . . ?
C12 N3 Ni1 O6 142.81(19) . . . . ?
O4 C10 O3 Ni1 24.1(4) . . . 4_676 ?
C9 C10 O3 Ni1 -153.99(15) . . . 4_676 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.351
_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_5
_database_code_depnum_ccdc_archive 'CCDC 1479969'
_audit_update_record             
;
2016-07-20 deposited with the CCDC.
2016-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H27 N8 O9 Zn2'
_chemical_formula_weight         846.40

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   P2/n

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

_cell_length_a                   15.566(3)
_cell_length_b                   6.9981(14)
_cell_length_c                   17.643(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.99(3)
_cell_angle_gamma                90.00
_cell_volume                     1827.9(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9908
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      27.24

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             862
_exptl_absorpt_coefficient_mu    1.379
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7606
_exptl_absorpt_correction_T_max  0.7994
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27098
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_sigmaI/netI    0.0221
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         27.59
_reflns_number_total             4211
_reflns_number_gt                3437
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0559P)²+1.8020P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4211
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1115
_refine_ls_wR_factor_gt          0.1039
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.513812(19) 0.34045(4) 0.344061(16) 0.03333(12) Uani 1 1 d . . .
C16 C 0.5513(3) 0.6218(6) 0.0592(2) 0.0655(10) Uani 1 1 d . . .
O1 O 0.59731(13) 0.2302(4) 0.43747(12) 0.0511(5) Uani 1 1 d . . .
O2 O 0.70352(16) 0.1892(4) 0.37929(12) 0.0629(7) Uani 1 1 d . . .
C2 C 0.74002(17) 0.1308(4) 0.51734(15) 0.0338(5) Uani 1 1 d . . .
C1 C 0.67693(19) 0.1901(4) 0.43744(15) 0.0387(6) Uani 1 1 d . . .
N1 N 0.55864(17) 0.5657(4) 0.29688(13) 0.0423(5) Uani 1 1 d . . .
C3 C 0.79616(18) -0.0246(4) 0.52212(15) 0.0405(6) Uani 1 1 d . . .
H3A H 0.7964 -0.0864 0.4755 0.049 Uiso 1 1 calc R . .
N2 N 0.5913(2) 0.7148(4) 0.20104(16) 0.0610(8) Uani 1 1 d . . .
C17 C 0.4625(4) 0.6543(7) 0.0217(3) 0.0894(15) Uani 1 1 d . . .
H17 H 0.4352 0.7608 0.0359 0.107 Uiso 1 1 calc R . .
C15 C 0.6069(4) 0.7500(9) 0.1239(2) 0.1065(19) Uani 1 1 d . . .
H15A H 0.6704 0.7303 0.1299 0.128 Uiso 1 1 calc R . .
H15B H 0.5924 0.8820 0.1084 0.128 Uiso 1 1 calc R . .
C13 C 0.6197(3) 0.8271(5) 0.2660(2) 0.0656(10) Uani 1 1 d . . .
H13A H 0.6480 0.9453 0.2694 0.079 Uiso 1 1 calc R . .
C12 C 0.5553(3) 0.5591(5) 0.22188(18) 0.0598(9) Uani 1 1 d . . .
H12A H 0.5309 0.4584 0.1876 0.072 Uiso 1 1 calc R . .
C14 C 0.5991(3) 0.7352(5) 0.3246(2) 0.0620(9) Uani 1 1 d . . .
H14A H 0.6107 0.7803 0.3764 0.074 Uiso 1 1 calc R . .
C18 C 0.5880(3) 0.4647(8) 0.0363(3) 0.0888(15) Uani 1 1 d . . .
H18 H 0.6488 0.4375 0.0607 0.107 Uiso 1 1 calc R . .
O1W O 0.7500 0.3508(18) 0.2500 0.288(7) Uani 1 2 d S . .
H1W1 H 0.7376 0.2800 0.2844 0.345 Uiso 0.50 1 d PR . .
C8 C 0.90941(18) -0.0725(4) 0.74476(15) 0.0371(6) Uani 1 1 d . . .
C6 C 0.79921(18) 0.1604(4) 0.66025(15) 0.0364(6) Uani 1 1 d . . .
H6A H 0.8009 0.2259 0.7065 0.044 Uiso 1 1 calc R . .
C5 C 0.85336(17) 0.0014(4) 0.66461(15) 0.0345(5) Uani 1 1 d . . .
C4 C 0.85197(18) -0.0908(4) 0.59444(15) 0.0385(6) Uani 1 1 d . . .
H4A H 0.8885 -0.1968 0.5961 0.046 Uiso 1 1 calc R . .
O3 O 0.96034(14) -0.2128(3) 0.74302(11) 0.0450(5) Uani 1 1 d . . .
O4 O 0.90210(15) -0.0001(3) 0.80584(11) 0.0529(5) Uani 1 1 d . . .
N4 N 0.68561(14) 0.3821(3) 0.58861(13) 0.0345(5) Uani 1 1 d . . .
N3 N 0.58385(15) 0.5621(3) 0.61202(13) 0.0375(5) Uani 1 1 d . . .
C9 C 0.61898(17) 0.3897(4) 0.62032(15) 0.0348(6) Uani 1 1 d . . .
H9A H 0.5998 0.2879 0.6449 0.042 Uiso 1 1 calc R . .
C7 C 0.74285(16) 0.2222(4) 0.58791(14) 0.0323(5) Uani 1 1 d . . .
C10 C 0.6939(2) 0.5535(4) 0.5560(2) 0.0474(7) Uani 1 1 d . . .
H10A H 0.7341 0.5889 0.5289 0.057 Uiso 1 1 calc R . .
C11 C 0.6325(3) 0.6559(4) 0.5716(2) 0.0588(9) Uani 1 1 d . . .
H11A H 0.6224 0.7832 0.5564 0.071 Uiso 1 1 calc 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 1.918(2) . ?
Zn1 O3 1.9369(19) 4 ?
Zn1 N1 2.006(2) . ?
Zn1 N3 2.026(2) 3_666 ?
C16 C17 1.355(6) . ?
C16 C18 1.356(6) . ?
C16 C15 1.498(6) . ?
O1 C1 1.271(3) . ?
O2 C1 1.219(3) . ?
C2 C3 1.381(4) . ?
C2 C7 1.388(4) . ?
C2 C1 1.506(4) . ?
N1 C12 1.309(4) . ?
N1 C14 1.362(4) . ?
C3 C4 1.383(4) . ?
C3 H3A 0.9300 . ?
N2 C12 1.328(4) . ?
N2 C13 1.347(4) . ?
N2 C15 1.476(4) . ?
C17 C18 1.365(7) 3_665 ?
C17 H17 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C13 C14 1.337(5) . ?
C13 H13A 0.9300 . ?
C12 H12A 0.9300 . ?
C14 H14A 0.9300 . ?
C18 C17 1.365(7) 3_665 ?
C18 H18 0.9300 . ?
O1W H1W1 0.8499 . ?
C8 O4 1.228(3) . ?
C8 O3 1.268(3) . ?
C8 C5 1.505(3) . ?
C6 C7 1.376(4) . ?
C6 C5 1.383(4) . ?
C6 H6A 0.9300 . ?
C5 C4 1.390(4) . ?
C4 H4A 0.9300 . ?
O3 Zn1 1.9369(19) 4_656 ?
N4 C9 1.323(3) . ?
N4 C10 1.354(3) . ?
N4 C7 1.433(3) . ?
N3 C9 1.314(3) . ?
N3 C11 1.360(4) . ?
N3 Zn1 2.026(2) 3_666 ?
C9 H9A 0.9300 . ?
C10 C11 1.290(4) . ?
C10 H10A 0.9300 . ?
C11 H11A 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
O1 Zn1 O3 126.16(11) . 4 ?
O1 Zn1 N1 116.26(10) . . ?
O3 Zn1 N1 94.93(9) 4 . ?
O1 Zn1 N3 101.31(9) . 3_666 ?
O3 Zn1 N3 110.32(10) 4 3_666 ?
N1 Zn1 N3 107.01(10) . 3_666 ?
C17 C16 C18 116.8(4) . . ?
C17 C16 C15 122.2(5) . . ?
C18 C16 C15 121.0(5) . . ?
C1 O1 Zn1 119.38(18) . . ?
C3 C2 C7 117.6(2) . . ?
C3 C2 C1 119.4(2) . . ?
C7 C2 C1 122.9(2) . . ?
O2 C1 O1 125.9(3) . . ?
O2 C1 C2 119.6(3) . . ?
O1 C1 C2 114.5(2) . . ?
C12 N1 C14 105.2(3) . . ?
C12 N1 Zn1 118.8(2) . . ?
C14 N1 Zn1 135.9(2) . . ?
C2 C3 C4 121.7(2) . . ?
C2 C3 H3A 119.2 . . ?
C4 C3 H3A 119.2 . . ?
C12 N2 C13 107.4(3) . . ?
C12 N2 C15 126.6(3) . . ?
C13 N2 C15 125.7(3) . . ?
C16 C17 C18 121.9(4) . 3_665 ?
C16 C17 H17 119.1 . . ?
C18 C17 H17 119.1 3_665 . ?
N2 C15 C16 112.4(3) . . ?
N2 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
N2 C15 H15B 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.9 . . ?
C14 C13 N2 106.4(3) . . ?
C14 C13 H13A 126.8 . . ?
N2 C13 H13A 126.8 . . ?
N1 C12 N2 111.3(3) . . ?
N1 C12 H12A 124.4 . . ?
N2 C12 H12A 124.4 . . ?
C13 C14 N1 109.7(3) . . ?
C13 C14 H14A 125.2 . . ?
N1 C14 H14A 125.2 . . ?
C16 C18 C17 121.3(4) . 3_665 ?
C16 C18 H18 119.3 . . ?
C17 C18 H18 119.3 3_665 . ?
O4 C8 O3 124.7(2) . . ?
O4 C8 C5 119.9(2) . . ?
O3 C8 C5 115.4(2) . . ?
C7 C6 C5 120.5(2) . . ?
C7 C6 H6A 119.8 . . ?
C5 C6 H6A 119.8 . . ?
C6 C5 C4 118.8(2) . . ?
C6 C5 C8 119.7(2) . . ?
C4 C5 C8 121.5(2) . . ?
C3 C4 C5 119.9(3) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C8 O3 Zn1 115.39(17) . 4_656 ?
C9 N4 C10 109.5(2) . . ?
C9 N4 C7 127.3(2) . . ?
C10 N4 C7 123.2(2) . . ?
C9 N3 C11 102.8(2) . . ?
C9 N3 Zn1 127.03(18) . 3_666 ?
C11 N3 Zn1 130.1(2) . 3_666 ?
N3 C9 N4 110.1(2) . . ?
N3 C9 H9A 124.9 . . ?
N4 C9 H9A 124.9 . . ?
C6 C7 C2 121.4(2) . . ?
C6 C7 N4 117.2(2) . . ?
C2 C7 N4 121.3(2) . . ?
C11 C10 N4 103.1(2) . . ?
C11 C10 H10A 128.4 . . ?
N4 C10 H10A 128.4 . . ?
C10 C11 N3 114.4(3) . . ?
C10 C11 H11A 122.8 . . ?
N3 C11 H11A 122.8 . . ?

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 O1 C1 69.2(3) 4 . . . ?
N1 Zn1 O1 C1 -49.5(3) . . . . ?
N3 Zn1 O1 C1 -165.0(2) 3_666 . . . ?
Zn1 O1 C1 O2 -11.2(4) . . . . ?
Zn1 O1 C1 C2 171.74(18) . . . . ?
C3 C2 C1 O2 -41.4(4) . . . . ?
C7 C2 C1 O2 140.6(3) . . . . ?
C3 C2 C1 O1 135.9(3) . . . . ?
C7 C2 C1 O1 -42.2(4) . . . . ?
O1 Zn1 N1 C12 124.6(3) . . . . ?
O3 Zn1 N1 C12 -10.1(3) 4 . . . ?
N3 Zn1 N1 C12 -123.1(3) 3_666 . . . ?
O1 Zn1 N1 C14 -51.2(4) . . . . ?
O3 Zn1 N1 C14 174.1(3) 4 . . . ?
N3 Zn1 N1 C14 61.1(4) 3_666 . . . ?
C7 C2 C3 C4 1.4(4) . . . . ?
C1 C2 C3 C4 -176.7(3) . . . . ?
C18 C16 C17 C18 0.0(8) . . . 3_665 ?
C15 C16 C17 C18 -179.0(4) . . . 3_665 ?
C12 N2 C15 C16 19.0(8) . . . . ?
C13 N2 C15 C16 -168.4(4) . . . . ?
C17 C16 C15 N2 78.3(6) . . . . ?
C18 C16 C15 N2 -100.7(6) . . . . ?
C12 N2 C13 C14 -0.4(5) . . . . ?
C15 N2 C13 C14 -174.2(5) . . . . ?
C14 N1 C12 N2 -0.1(4) . . . . ?
Zn1 N1 C12 N2 -177.1(2) . . . . ?
C13 N2 C12 N1 0.3(5) . . . . ?
C15 N2 C12 N1 174.0(4) . . . . ?
N2 C13 C14 N1 0.4(5) . . . . ?
C12 N1 C14 C13 -0.2(5) . . . . ?
Zn1 N1 C14 C13 176.0(3) . . . . ?
C17 C16 C18 C17 0.0(8) . . . 3_665 ?
C15 C16 C18 C17 179.0(4) . . . 3_665 ?
C7 C6 C5 C4 2.1(4) . . . . ?
C7 C6 C5 C8 -175.5(2) . . . . ?
O4 C8 C5 C6 5.1(4) . . . . ?
O3 C8 C5 C6 -176.7(3) . . . . ?
O4 C8 C5 C4 -172.4(3) . . . . ?
O3 C8 C5 C4 5.8(4) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
C6 C5 C4 C3 -0.9(4) . . . . ?
C8 C5 C4 C3 176.7(3) . . . . ?
O4 C8 O3 Zn1 10.0(4) . . . 4_656 ?
C5 C8 O3 Zn1 -168.14(18) . . . 4_656 ?
C11 N3 C9 N4 1.4(3) . . . . ?
Zn1 N3 C9 N4 -175.44(17) 3_666 . . . ?
C10 N4 C9 N3 -1.7(3) . . . . ?
C7 N4 C9 N3 177.6(2) . . . . ?
C5 C6 C7 C2 -1.5(4) . . . . ?
C5 C6 C7 N4 177.0(2) . . . . ?
C3 C2 C7 C6 -0.2(4) . . . . ?
C1 C2 C7 C6 177.8(3) . . . . ?
C3 C2 C7 N4 -178.7(2) . . . . ?
C1 C2 C7 N4 -0.7(4) . . . . ?
C9 N4 C7 C6 -65.0(4) . . . . ?
C10 N4 C7 C6 114.2(3) . . . . ?
C9 N4 C7 C2 113.5(3) . . . . ?
C10 N4 C7 C2 -67.2(4) . . . . ?
C9 N4 C10 C11 1.3(4) . . . . ?
C7 N4 C10 C11 -178.1(3) . . . . ?
N4 C10 C11 N3 -0.4(4) . . . . ?
C9 N3 C11 C10 -0.6(4) . . . . ?
Zn1 N3 C11 C10 176.1(2) 3_666 . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.59
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.028
_refine_diff_density_min         -0.654
_refine_diff_density_rms         0.071
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1479970'
_audit_update_record             
;
2016-07-20 deposited with the CCDC.
2016-08-17 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 Cd N4 O6'
_chemical_formula_weight         497.76

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'
Cd Cd -0.8075 1.2024 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   29.9762(12)
_cell_length_b                   6.7809(3)
_cell_length_c                   21.3475(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 121.7340(10)
_cell_angle_gamma                90.00
_cell_volume                     3690.5(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9910
_cell_measurement_theta_min      3.108
_cell_measurement_theta_max      27.535

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.501
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.138
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.792
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1992
_exptl_absorpt_coefficient_mu    1.229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8783
_exptl_absorpt_correction_T_max  0.9534
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20718
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.60
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3244
_reflns_number_gt                3043
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0578P)²+4.1751P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3244
_refine_ls_number_parameters     269
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0256
_refine_ls_wR_factor_ref         0.0839
_refine_ls_wR_factor_gt          0.0728
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.003
_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
C1 C 0.99918(11) 1.1083(4) 1.11907(16) 0.0309(6) Uani 1 1 d . . .
H1 H 1.0119 1.0088 1.1026 0.037 Uiso 1 1 calc R . .
C2 C 0.95259(13) 1.2642(5) 1.1542(2) 0.0500(9) Uani 1 1 d . . .
H2 H 0.9281 1.2945 1.1669 0.060 Uiso 1 1 calc R . .
C3 C 0.98875(15) 1.3865(4) 1.1563(2) 0.0516(10) Uani 1 1 d . . .
H3 H 0.9929 1.5185 1.1702 0.062 Uiso 1 1 calc R . .
C4 C 0.92703(10) 0.9171(4) 1.11621(14) 0.0247(5) Uani 1 1 d . . .
C5 C 0.92085(10) 0.8501(4) 1.17252(14) 0.0265(5) Uani 1 1 d . . .
H5 H 0.9379 0.9137 1.2179 0.032 Uiso 1 1 calc R . .
C6 C 0.88919(10) 0.6879(4) 1.16117(14) 0.0273(5) Uani 1 1 d . . .
C7 C 0.86282(13) 0.5992(4) 1.09208(17) 0.0375(7) Uani 1 1 d . . .
H7 H 0.8402 0.4944 1.0830 0.045 Uiso 1 1 calc R . .
C8 C 0.86995(12) 0.6653(5) 1.03714(16) 0.0409(7) Uani 1 1 d . . .
H8 H 0.8525 0.6026 0.9916 0.049 Uiso 1 1 calc R . .
C9 C 0.90262(10) 0.8234(4) 1.04818(14) 0.0295(5) Uani 1 1 d . . .
C10 C 0.91005(12) 0.8868(4) 0.98603(15) 0.0321(7) Uani 1 1 d . . .
C11 C 0.88791(11) 0.5979(4) 1.22443(16) 0.0296(6) Uani 1 1 d . . .
C12 C 0.79099(11) 0.6994(5) 0.82469(16) 0.0386(7) Uani 1 1 d . . .
H12 H 0.7923 0.8306 0.8132 0.046 Uiso 1 1 calc R . .
C13 C 0.75101(13) 0.6151(5) 0.8261(2) 0.0446(8) Uani 1 1 d . . .
H13 H 0.7201 0.6761 0.8158 0.053 Uiso 1 1 calc R . .
C14 C 0.81175(12) 0.3984(4) 0.85501(17) 0.0348(7) Uani 1 1 d . . .
H14 H 0.8299 0.2795 0.8686 0.042 Uiso 1 1 calc R . .
C15 C 0.73251(13) 0.2728(6) 0.85291(17) 0.0483(8) Uani 1 1 d . . .
H15A H 0.7403 0.1455 0.8401 0.058 Uiso 1 1 calc R . .
H15B H 0.6957 0.3007 0.8184 0.058 Uiso 1 1 calc R . .
C16 C 0.74201(10) 0.2619(4) 0.92943(15) 0.0369(6) Uani 1 1 d . . .
C17 C 0.71433(15) 0.3800(5) 0.9495(2) 0.0490(9) Uani 1 1 d . . .
H17 H 0.6899 0.4690 0.9157 0.059 Uiso 1 1 calc R . .
C18 C 0.77770(15) 0.1317(5) 0.9804(2) 0.0507(8) Uani 1 1 d . . .
H18 H 0.7968 0.0504 0.9678 0.061 Uiso 1 1 calc R . .
Cd1 Cd 0.906598(7) 0.60593(3) 0.851059(10) 0.02753(11) Uani 1 1 d . . .
N1 N 1.01822(8) 1.2882(3) 1.13524(12) 0.0313(5) Uani 1 1 d . . .
N2 N 0.95893(9) 1.0867(3) 1.12946(13) 0.0269(5) Uani 1 1 d . . .
N3 N 0.82943(9) 0.5624(4) 0.84278(12) 0.0304(5) Uani 1 1 d . . .
N4 N 0.76440(10) 0.4244(4) 0.84538(13) 0.0350(6) Uani 1 1 d . . .
O1 O 0.90399(11) 0.6975(3) 1.28188(12) 0.0534(6) Uani 1 1 d . . .
O2 O 0.87518(9) 0.4219(3) 1.22036(12) 0.0424(5) Uani 1 1 d . . .
O3 O 0.89061(11) 1.0460(4) 0.95511(13) 0.0528(6) Uani 1 1 d . . .
O4 O 0.93502(9) 0.7707(4) 0.97022(11) 0.0455(5) Uani 1 1 d . . .
O5 O 0.95326(11) 0.3546(4) 0.94332(14) 0.0654(8) Uani 1 1 d . . .
H5A H 0.9845 0.3446 0.9524 0.098 Uiso 1 1 d R . .
H5B H 0.9375 0.2443 0.9272 0.098 Uiso 1 1 d R . .
O6 O 0.87530(8) 0.9534(3) 0.81761(11) 0.0388(4) Uani 1 1 d D . .
H6A H 0.8641(11) 0.980(6) 0.8444(16) 0.800 Uiso 1 1 d D . .
H6B H 0.8813(17) 1.050(4) 0.800(2) 0.080 Uiso 1 1 d 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
C1 N1 1.314(3) . ?
C1 N2 1.344(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.346(5) . ?
C2 N2 1.367(4) . ?
C2 H2 0.9300 . ?
C3 N1 1.359(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(4) . ?
C4 C9 1.389(4) . ?
C4 N2 1.426(3) . ?
C5 C6 1.388(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.391(4) . ?
C6 C11 1.501(4) . ?
C7 C8 1.373(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.386(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.518(4) . ?
C10 O3 1.240(4) . ?
C10 O4 1.249(4) . ?
C11 O2 1.242(3) . ?
C11 O1 1.253(4) . ?
C12 C13 1.342(5) . ?
C12 N3 1.368(4) . ?
C12 H12 0.9300 . ?
C13 N4 1.352(4) . ?
C13 H13 0.9300 . ?
C14 N3 1.316(4) . ?
C14 N4 1.334(4) . ?
C14 H14 0.9300 . ?
C15 N4 1.469(4) . ?
C15 C16 1.505(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C18 1.372(5) . ?
C16 C17 1.374(5) . ?
C17 C18 1.387(5) 7_657 ?
C17 H17 0.9300 . ?
C18 C17 1.387(5) 7_657 ?
C18 H18 0.9300 . ?
Cd1 N1 2.233(2) 5_777 ?
Cd1 N3 2.245(2) . ?
Cd1 O5 2.417(2) . ?
Cd1 O2 2.438(2) 6_565 ?
Cd1 O4 2.483(2) . ?
Cd1 O6 2.497(2) . ?
Cd1 O1 2.510(2) 6_565 ?
N1 Cd1 2.233(2) 5_777 ?
O1 Cd1 2.510(2) 6_566 ?
O2 Cd1 2.438(2) 6_566 ?
O5 H5A 0.8542 . ?
O5 H5B 0.8542 . ?
O6 H6A 0.8200(11) . ?
O6 H6B 0.8200(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 N2 111.2(2) . . ?
N1 C1 H1 124.4 . . ?
N2 C1 H1 124.4 . . ?
C3 C2 N2 106.4(3) . . ?
C3 C2 H2 126.8 . . ?
N2 C2 H2 126.8 . . ?
C2 C3 N1 109.8(3) . . ?
C2 C3 H3 125.1 . . ?
N1 C3 H3 125.1 . . ?
C5 C4 C9 121.3(2) . . ?
C5 C4 N2 118.3(2) . . ?
C9 C4 N2 120.4(2) . . ?
C4 C5 C6 120.0(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C7 118.9(2) . . ?
C5 C6 C11 120.3(2) . . ?
C7 C6 C11 120.6(2) . . ?
C8 C7 C6 120.5(3) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 121.4(3) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C8 C9 C4 117.9(2) . . ?
C8 C9 C10 119.1(2) . . ?
C4 C9 C10 123.1(2) . . ?
O3 C10 O4 125.9(3) . . ?
O3 C10 C9 117.9(3) . . ?
O4 C10 C9 116.2(2) . . ?
O2 C11 O1 122.1(3) . . ?
O2 C11 C6 118.7(3) . . ?
O1 C11 C6 118.9(2) . . ?
C13 C12 N3 109.5(3) . . ?
C13 C12 H12 125.2 . . ?
N3 C12 H12 125.2 . . ?
C12 C13 N4 106.7(3) . . ?
C12 C13 H13 126.6 . . ?
N4 C13 H13 126.6 . . ?
N3 C14 N4 111.4(3) . . ?
N3 C14 H14 124.3 . . ?
N4 C14 H14 124.3 . . ?
N4 C15 C16 113.0(2) . . ?
N4 C15 H15A 109.0 . . ?
C16 C15 H15A 109.0 . . ?
N4 C15 H15B 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C18 C16 C17 118.3(3) . . ?
C18 C16 C15 121.0(3) . . ?
C17 C16 C15 120.6(3) . . ?
C16 C17 C18 120.9(3) . 7_657 ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 7_657 . ?
C16 C18 C17 120.8(3) . 7_657 ?
C16 C18 H18 119.6 . . ?
C17 C18 H18 119.6 7_657 . ?
N1 Cd1 N3 168.46(8) 5_777 . ?
N1 Cd1 O5 90.47(9) 5_777 . ?
N3 Cd1 O5 95.87(9) . . ?
N1 Cd1 O2 86.01(8) 5_777 6_565 ?
N3 Cd1 O2 97.93(8) . 6_565 ?
O5 Cd1 O2 125.99(9) . 6_565 ?
N1 Cd1 O4 86.70(8) 5_777 . ?
N3 Cd1 O4 85.63(8) . . ?
O5 Cd1 O4 75.10(9) . . ?
O2 Cd1 O4 157.70(7) 6_565 . ?
N1 Cd1 O6 86.32(8) 5_777 . ?
N3 Cd1 O6 83.39(8) . . ?
O5 Cd1 O6 150.18(9) . . ?
O2 Cd1 O6 83.39(7) 6_565 . ?
O4 Cd1 O6 75.12(7) . . ?
N1 Cd1 O1 93.30(8) 5_777 6_565 ?
N3 Cd1 O1 97.71(9) . 6_565 ?
O5 Cd1 O1 74.16(9) . 6_565 ?
O2 Cd1 O1 52.36(7) 6_565 6_565 ?
O4 Cd1 O1 149.26(7) . 6_565 ?
O6 Cd1 O1 135.60(7) . 6_565 ?
C1 N1 C3 105.9(2) . . ?
C1 N1 Cd1 127.01(19) . 5_777 ?
C3 N1 Cd1 125.90(19) . 5_777 ?
C1 N2 C2 106.7(2) . . ?
C1 N2 C4 128.4(2) . . ?
C2 N2 C4 124.9(2) . . ?
C14 N3 C12 105.2(2) . . ?
C14 N3 Cd1 127.0(2) . . ?
C12 N3 Cd1 127.83(19) . . ?
C14 N4 C13 107.1(2) . . ?
C14 N4 C15 126.2(3) . . ?
C13 N4 C15 126.6(3) . . ?
C11 O1 Cd1 90.63(17) . 6_566 ?
C11 O2 Cd1 94.29(19) . 6_566 ?
C10 O4 Cd1 128.98(19) . . ?
Cd1 O5 H5A 109.6 . . ?
Cd1 O5 H5B 109.2 . . ?
H5A O5 H5B 109.3 . . ?
Cd1 O6 H6A 104(3) . . ?
Cd1 O6 H6B 138(3) . . ?
H6A O6 H6B 114.6(2) . . ?

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
N2 C2 C3 N1 -1.4(5) . . . . ?
C9 C4 C5 C6 -0.9(4) . . . . ?
N2 C4 C5 C6 178.6(2) . . . . ?
C4 C5 C6 C7 -2.0(4) . . . . ?
C4 C5 C6 C11 171.8(2) . . . . ?
C5 C6 C7 C8 3.0(5) . . . . ?
C11 C6 C7 C8 -170.8(3) . . . . ?
C6 C7 C8 C9 -1.2(5) . . . . ?
C7 C8 C9 C4 -1.7(5) . . . . ?
C7 C8 C9 C10 178.5(3) . . . . ?
C5 C4 C9 C8 2.7(4) . . . . ?
N2 C4 C9 C8 -176.8(3) . . . . ?
C5 C4 C9 C10 -177.5(3) . . . . ?
N2 C4 C9 C10 3.1(4) . . . . ?
C8 C9 C10 O3 110.0(3) . . . . ?
C4 C9 C10 O3 -69.9(4) . . . . ?
C8 C9 C10 O4 -69.2(4) . . . . ?
C4 C9 C10 O4 110.9(3) . . . . ?
C5 C6 C11 O2 -155.3(3) . . . . ?
C7 C6 C11 O2 18.4(4) . . . . ?
C5 C6 C11 O1 18.7(4) . . . . ?
C7 C6 C11 O1 -167.6(3) . . . . ?
N3 C12 C13 N4 0.2(4) . . . . ?
N4 C15 C16 C18 -94.0(4) . . . . ?
N4 C15 C16 C17 87.2(4) . . . . ?
C18 C16 C17 C18 0.1(6) . . . 7_657 ?
C15 C16 C17 C18 178.9(3) . . . 7_657 ?
C17 C16 C18 C17 -0.1(6) . . . 7_657 ?
C15 C16 C18 C17 -178.9(3) . . . 7_657 ?
N2 C1 N1 C3 -0.5(4) . . . . ?
N2 C1 N1 Cd1 167.62(17) . . . 5_777 ?
C2 C3 N1 C1 1.2(4) . . . . ?
C2 C3 N1 Cd1 -167.1(3) . . . 5_777 ?
N1 C1 N2 C2 -0.4(4) . . . . ?
N1 C1 N2 C4 178.0(2) . . . . ?
C3 C2 N2 C1 1.1(4) . . . . ?
C3 C2 N2 C4 -177.4(3) . . . . ?
C5 C4 N2 C1 128.0(3) . . . . ?
C9 C4 N2 C1 -52.4(4) . . . . ?
C5 C4 N2 C2 -53.8(4) . . . . ?
C9 C4 N2 C2 125.7(3) . . . . ?
N4 C14 N3 C12 0.2(3) . . . . ?
N4 C14 N3 Cd1 179.76(18) . . . . ?
C13 C12 N3 C14 -0.2(4) . . . . ?
C13 C12 N3 Cd1 -179.8(2) . . . . ?
N1 Cd1 N3 C14 -151.5(4) 5_777 . . . ?
O5 Cd1 N3 C14 -28.5(3) . . . . ?
O2 Cd1 N3 C14 99.1(2) 6_565 . . . ?
O4 Cd1 N3 C14 -103.0(2) . . . . ?
O6 Cd1 N3 C14 -178.5(2) . . . . ?
O1 Cd1 N3 C14 46.2(2) 6_565 . . . ?
N1 Cd1 N3 C12 27.9(5) 5_777 . . . ?
O5 Cd1 N3 C12 150.9(2) . . . . ?
O2 Cd1 N3 C12 -81.5(2) 6_565 . . . ?
O4 Cd1 N3 C12 76.4(2) . . . . ?
O6 Cd1 N3 C12 0.9(2) . . . . ?
O1 Cd1 N3 C12 -134.4(2) 6_565 . . . ?
N3 C14 N4 C13 -0.1(4) . . . . ?
N3 C14 N4 C15 178.8(3) . . . . ?
C12 C13 N4 C14 0.0(4) . . . . ?
C12 C13 N4 C15 -178.9(3) . . . . ?
C16 C15 N4 C14 91.3(4) . . . . ?
C16 C15 N4 C13 -90.0(4) . . . . ?
O2 C11 O1 Cd1 7.7(3) . . . 6_566 ?
C6 C11 O1 Cd1 -166.1(2) . . . 6_566 ?
O1 C11 O2 Cd1 -7.9(3) . . . 6_566 ?
C6 C11 O2 Cd1 165.8(2) . . . 6_566 ?
O3 C10 O4 Cd1 -58.0(4) . . . . ?
C9 C10 O4 Cd1 121.2(2) . . . . ?
N1 Cd1 O4 C10 130.6(3) 5_777 . . . ?
N3 Cd1 O4 C10 -40.7(3) . . . . ?
O5 Cd1 O4 C10 -138.0(3) . . . . ?
O2 Cd1 O4 C10 59.5(3) 6_565 . . . ?
O6 Cd1 O4 C10 43.6(2) . . . . ?
O1 Cd1 O4 C10 -138.5(2) 6_565 . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.619
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.182
