# Electronic Supplementary Material (ESI) for RSC Advances.
# 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 1490728'
_audit_update_record             
;
2016-07-05 deposited with the CCDC.
2016-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H15 N3 O7 Zn'
_chemical_formula_weight         390.65

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7775(9)
_cell_length_b                   9.6775(10)
_cell_length_c                   9.8961(10)
_cell_angle_alpha                81.460(4)
_cell_angle_beta                 69.986(5)
_cell_angle_gamma                78.630(4)
_cell_volume                     771.35(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5944
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      28.14

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    1.635
_shelx_estimated_absorpt_T_min   0.623
_shelx_estimated_absorpt_T_max   0.746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6
_exptl_absorpt_correction_T_max  0.7
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11962
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.199
_diffrn_reflns_theta_max         28.288
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3778
_reflns_number_gt                3142
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1999)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury CSD 3.5.1, 2008'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0602P)²+0.3263P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3778
_refine_ls_number_parameters     233
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1046
_refine_ls_wR_factor_gt          0.0978
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.53235(4) 0.61905(3) 0.62539(3) 0.02393(11) Uani 1 1 d . . . . .
O1 O 0.3730(2) 0.48359(18) 0.70262(19) 0.0286(4) Uani 1 1 d . . . . .
O2 O 0.3973(2) 0.30204(19) 0.57829(18) 0.0306(4) Uani 1 1 d . . . . .
O3 O 0.0841(3) -0.1432(2) 1.1892(2) 0.0376(5) Uani 1 1 d . . . . .
O4 O 0.4489(3) 0.3375(2) 1.1931(2) 0.0366(5) Uani 1 1 d . . . . .
O5 O 0.2760(3) 0.1968(2) 1.3316(2) 0.0418(5) Uani 1 1 d . . . . .
O6 O 0.7194(3) 0.4457(2) 0.6072(2) 0.0414(5) Uani 1 1 d . . . . .
O7 O 0.3184(3) 0.7935(2) 0.6588(2) 0.0383(5) Uani 1 1 d . . . . .
N1 N 0.2311(3) -0.0952(2) 0.9540(2) 0.0297(5) Uani 1 1 d D . . . .
N2 N 0.9591(4) 0.3046(3) 0.5267(3) 0.0436(6) Uani 1 1 d D . . . .
N3 N 0.1794(5) 0.9872(3) 0.5727(4) 0.0636(9) Uani 1 1 d D . . . .
C1 C 0.3783(3) 0.3554(2) 0.6928(2) 0.0217(5) Uani 1 1 d . . . . .
C2 C 0.3535(3) 0.2568(2) 0.8276(2) 0.0206(5) Uani 1 1 d . . . . .
C3 C 0.3080(3) 0.1263(3) 0.8321(2) 0.0233(5) Uani 1 1 d . . . . .
H3 H 0.3005 0.0983 0.7490 0.028 Uiso 1 1 calc R U . . .
C4 C 0.2734(3) 0.0364(2) 0.9591(2) 0.0233(5) Uani 1 1 d . . . . .
C5 C 0.2872(3) 0.0788(3) 1.0827(2) 0.0255(5) Uani 1 1 d . . . . .
H5 H 0.2622 0.0210 1.1687 0.031 Uiso 1 1 calc R U . . .
C6 C 0.3378(3) 0.2068(3) 1.0775(2) 0.0237(5) Uani 1 1 d . . . . .
C7 C 0.3710(3) 0.2970(2) 0.9506(2) 0.0223(5) Uani 1 1 d . . . . .
H7 H 0.4044 0.3831 0.9480 0.027 Uiso 1 1 calc R U . . .
C8 C 0.1439(3) -0.1777(3) 1.0661(3) 0.0294(5) Uani 1 1 d . . . . .
C9 C 0.1184(5) -0.3118(3) 1.0197(3) 0.0464(8) Uani 1 1 d . . . . .
H9A H 0.0356 -0.2878 0.9720 0.056 Uiso 1 1 calc R U . . .
H9B H 0.2200 -0.3518 0.9502 0.056 Uiso 1 1 calc R U . . .
C10 C 0.0661(4) -0.4212(3) 1.1435(3) 0.0414(7) Uani 1 1 d . . . . .
H10A H -0.0299 -0.3802 1.2161 0.062 Uiso 1 1 calc R U . . .
H10B H 0.1532 -0.4538 1.1840 0.062 Uiso 1 1 calc R U . . .
H10C H 0.0415 -0.4994 1.1096 0.062 Uiso 1 1 calc R U . . .
C11 C 0.3542(3) 0.2495(3) 1.2115(3) 0.0261(5) Uani 1 1 d . . . . .
C12 C 0.8437(4) 0.4052(3) 0.5086(3) 0.0350(6) Uani 1 1 d . . . . .
H12 H 0.8558 0.4488 0.4160 0.042 Uiso 1 1 calc R U . . .
C13 C 0.2968(5) 0.8861(3) 0.5634(4) 0.0469(8) Uani 1 1 d . . . . .
H13 H 0.3775 0.8805 0.4735 0.056 Uiso 1 1 calc R U . . .
H3A H 0.103(4) 1.004(4) 0.657(3) 0.070 Uiso 1 1 d D U . . .
H3B H 0.176(5) 1.058(3) 0.504(3) 0.070 Uiso 1 1 d D U . . .
H1 H 0.268(5) -0.135(4) 0.873(3) 0.070 Uiso 1 1 d D U . . .
H2A H 0.949(5) 0.253(4) 0.613(3) 0.070 Uiso 1 1 d D U . . .
H2B H 1.050(3) 0.283(4) 0.456(3) 0.070 Uiso 1 1 d D U . . .


_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 1.9713(18) 2_667 ?
Zn1 O2 1.9758(17) 2_666 ?
Zn1 O1 1.9882(17) . ?
Zn1 O6 2.084(2) . ?
Zn1 O7 2.231(2) . ?
O1 C1 1.249(3) . ?
O2 C1 1.261(3) . ?
O2 Zn1 1.9758(17) 2_666 ?
O3 C8 1.218(3) . ?
O4 C11 1.256(3) . ?
O4 Zn1 1.9713(17) 2_667 ?
O5 C11 1.242(3) . ?
O6 C12 1.230(4) . ?
O7 C13 1.238(4) . ?
N1 C8 1.360(3) . ?
N1 C4 1.408(3) . ?
N1 H1 0.877(19) . ?
N2 C12 1.300(4) . ?
N2 H2A 0.910(19) . ?
N2 H2B 0.876(19) . ?
N3 C13 1.262(5) . ?
N3 H3A 0.888(18) . ?
N3 H3B 0.891(14) . ?
C1 C2 1.498(3) . ?
C2 C3 1.388(3) . ?
C2 C7 1.396(3) . ?
C3 C4 1.396(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.396(3) . ?
C5 C6 1.384(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.395(3) . ?
C6 C11 1.506(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.519(4) . ?
C9 C10 1.502(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C12 H12 0.9300 . ?
C13 H13 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
O4 Zn1 O2 135.49(8) 2_667 2_666 ?
O4 Zn1 O1 100.09(8) 2_667 . ?
O2 Zn1 O1 123.54(7) 2_666 . ?
O4 Zn1 O6 91.91(9) 2_667 . ?
O2 Zn1 O6 97.67(8) 2_666 . ?
O1 Zn1 O6 87.73(8) . . ?
O4 Zn1 O7 87.01(8) 2_667 . ?
O2 Zn1 O7 86.32(8) 2_666 . ?
O1 Zn1 O7 87.90(8) . . ?
O6 Zn1 O7 175.24(8) . . ?
C1 O1 Zn1 134.91(17) . . ?
C1 O2 Zn1 130.75(16) . 2_666 ?
C11 O4 Zn1 113.34(16) . 2_667 ?
C12 O6 Zn1 133.8(2) . . ?
C13 O7 Zn1 124.2(2) . . ?
C8 N1 C4 127.4(2) . . ?
C8 N1 H1 113(3) . . ?
C4 N1 H1 120(3) . . ?
C12 N2 H2A 122(3) . . ?
C12 N2 H2B 122(3) . . ?
H2A N2 H2B 117(4) . . ?
C13 N3 H3A 120(3) . . ?
C13 N3 H3B 125(3) . . ?
H3A N3 H3B 114(3) . . ?
O1 C1 O2 125.1(2) . . ?
O1 C1 C2 118.3(2) . . ?
O2 C1 C2 116.6(2) . . ?
C3 C2 C7 119.6(2) . . ?
C3 C2 C1 119.99(19) . . ?
C7 C2 C1 120.4(2) . . ?
C2 C3 C4 121.1(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 118.9(2) . . ?
C3 C4 N1 117.6(2) . . ?
C5 C4 N1 123.4(2) . . ?
C6 C5 C4 120.1(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 120.8(2) . . ?
C5 C6 C11 119.2(2) . . ?
C7 C6 C11 119.9(2) . . ?
C6 C7 C2 119.3(2) . . ?
C6 C7 H7 120.3 . . ?
C2 C7 H7 120.3 . . ?
O3 C8 N1 123.3(2) . . ?
O3 C8 C9 123.6(2) . . ?
N1 C8 C9 112.9(2) . . ?
C10 C9 C8 113.0(2) . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O5 C11 O4 124.1(2) . . ?
O5 C11 C6 119.3(2) . . ?
O4 C11 C6 116.6(2) . . ?
O6 C12 N2 123.6(3) . . ?
O6 C12 H12 118.2 . . ?
N2 C12 H12 118.2 . . ?
O7 C13 N3 128.3(4) . . ?
O7 C13 H13 115.8 . . ?
N3 C13 H13 115.8 . . ?

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
Zn1 O1 C1 O2 -66.0(3) . . . . ?
Zn1 O1 C1 C2 116.8(2) . . . . ?
Zn1 O2 C1 O1 13.8(4) 2_666 . . . ?
Zn1 O2 C1 C2 -168.94(16) 2_666 . . . ?
O1 C1 C2 C3 160.1(2) . . . . ?
O2 C1 C2 C3 -17.4(3) . . . . ?
O1 C1 C2 C7 -18.0(3) . . . . ?
O2 C1 C2 C7 164.5(2) . . . . ?
C7 C2 C3 C4 2.4(4) . . . . ?
C1 C2 C3 C4 -175.7(2) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C2 C3 C4 N1 -178.9(2) . . . . ?
C8 N1 C4 C3 -156.9(3) . . . . ?
C8 N1 C4 C5 25.1(4) . . . . ?
C3 C4 C5 C6 -1.4(4) . . . . ?
N1 C4 C5 C6 176.6(2) . . . . ?
C4 C5 C6 C7 2.0(4) . . . . ?
C4 C5 C6 C11 -179.1(2) . . . . ?
C5 C6 C7 C2 -0.3(4) . . . . ?
C11 C6 C7 C2 -179.3(2) . . . . ?
C3 C2 C7 C6 -1.8(4) . . . . ?
C1 C2 C7 C6 176.2(2) . . . . ?
C4 N1 C8 O3 3.0(5) . . . . ?
C4 N1 C8 C9 178.8(3) . . . . ?
O3 C8 C9 C10 -20.5(5) . . . . ?
N1 C8 C9 C10 163.7(3) . . . . ?
Zn1 O4 C11 O5 1.7(4) 2_667 . . . ?
Zn1 O4 C11 C6 -177.92(17) 2_667 . . . ?
C5 C6 C11 O5 -22.7(4) . . . . ?
C7 C6 C11 O5 156.2(3) . . . . ?
C5 C6 C11 O4 156.9(2) . . . . ?
C7 C6 C11 O4 -24.2(4) . . . . ?
Zn1 O6 C12 N2 168.6(2) . . . . ?
Zn1 O7 C13 N3 179.3(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3B O5 0.891(14) 2.06(2) 2.896(4) 155(4) 1_564
N3 H3A O3 0.888(18) 2.20(3) 3.021(4) 153(4) 2_567
N2 H2B O5 0.876(19) 2.03(2) 2.886(4) 165(4) 1_654
N2 H2A O3 0.910(19) 2.038(19) 2.948(3) 177(4) 2_657
N1 H1 O7 0.877(19) 2.19(2) 3.059(3) 168(4) 1_545
C12 H12 O1 0.93 2.59 3.223(3) 125.8 2_666
C13 H13 O2 0.93 2.34 2.958(4) 123.3 2_666
C5 H5 O3 0.93 2.38 2.908(3) 115.6 .

_refine_diff_density_max         1.172
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.102

_shelxl_version_number           2014/6

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

data_2
_database_code_depnum_ccdc_archive 'CCDC 1490729'
_audit_update_record             
;
2016-07-05 deposited with the CCDC.
2016-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H58 N8 O18 Zn2'
_chemical_formula_weight         1165.76

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.777(2)
_cell_length_b                   15.197(3)
_cell_length_c                   17.163(3)
_cell_angle_alpha                115.964(6)
_cell_angle_beta                 103.286(7)
_cell_angle_gamma                90.579(7)
_cell_volume                     2666.3(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9867
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      28.21

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_F_000             1212
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.979
_shelx_estimated_absorpt_T_min   0.738
_shelx_estimated_absorpt_T_max   0.836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7
_exptl_absorpt_correction_T_max  0.8
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            52466
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.188
_diffrn_reflns_theta_max         28.333
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             13182
_reflns_number_gt                10717
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1999)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury CSD 3.5.1, 2008'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0593P)²+0.7178P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         13182
_refine_ls_number_parameters     711
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1062
_refine_ls_wR_factor_gt          0.0986
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.091
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.67588(2) 0.71953(2) 0.66757(2) 0.02455(6) Uani 1 1 d . . . . .
Zn2 Zn 1.13218(2) 1.20585(2) 0.62667(2) 0.02650(6) Uani 1 1 d . . . . .
O1 O 0.50938(11) 0.67087(10) 0.63034(10) 0.0351(3) Uani 1 1 d . . . . .
O15 O 0.14176(18) 0.55000(18) 0.24925(15) 0.0729(6) Uani 1 1 d . . . . .
O2 O 0.54849(13) 0.53466(12) 0.64215(14) 0.0521(4) Uani 1 1 d . . . . .
O5 O 0.0495(3) 0.75394(19) 0.8260(2) 0.1232(13) Uani 1 1 d . . . . .
O17 O 0.36918(19) 0.74327(16) 0.51987(14) 0.0697(6) Uani 1 1 d . . . . .
O18 O 0.3487(2) 0.9450(2) 0.73867(17) 0.0896(8) Uani 1 1 d . . . . .
O4 O 0.20457(12) 0.33587(9) 0.64823(10) 0.0340(3) Uani 1 1 d . . . . .
O6 O 0.71919(13) 0.84218(10) 0.66641(10) 0.0362(3) Uani 1 1 d . . . . .
O10 O 0.5520(3) 1.25029(18) 0.86247(18) 0.0970(9) Uani 1 1 d . . . . .
O8 O 0.97287(12) 1.19786(10) 0.64629(10) 0.0384(3) Uani 1 1 d . . . . .
O11 O 1.04760(12) 1.15560(10) 0.48329(10) 0.0370(3) Uani 1 1 d . . . . .
O9 O 1.00442(13) 1.04443(11) 0.61590(11) 0.0425(3) Uani 1 1 d . . . . .
O16 O 0.36541(18) 0.62445(13) 0.34392(14) 0.0612(5) Uani 1 1 d . . . . .
N1 N 0.14727(16) 0.76124(12) 0.73173(13) 0.0409(4) Uani 1 1 d . . . . .
H1 H 0.1606 0.7964 0.7061 0.049 Uiso 1 1 calc R U . . .
N5 N 0.78166(13) 0.63328(11) 0.59598(10) 0.0265(3) Uani 1 1 d . . . . .
N2 N 0.60558(16) 1.25612(12) 0.74757(12) 0.0379(4) Uani 1 1 d . . . . .
H2 H 0.6007 1.2881 0.7164 0.045 Uiso 1 1 calc R U . . .
N4 N 0.80085(16) 0.77351(13) 1.23306(11) 0.0365(4) Uani 1 1 d . . . . .
N6 N 1.26543(13) 1.12384(11) 0.58015(10) 0.0269(3) Uani 1 1 d . . . . .
N3 N 0.72384(15) 0.73592(12) 0.79651(11) 0.0341(4) Uani 1 1 d . . . . .
N8 N 0.6084(2) 0.15343(19) 0.04205(18) 0.0700(7) Uani 1 1 d . . . . .
C46 C 0.6080(3) 0.1167(2) 0.0987(2) 0.0668(8) Uani 1 1 d . . . . .
H46 H 0.5852 0.1562 0.1503 0.080 Uiso 1 1 calc R U . . .
O13 O 0.6343(2) 0.03694(17) 0.09068(15) 0.0778(6) Uani 1 1 d . . . . .
O12 O 0.8723(2) 0.45767(19) 0.91790(16) 0.0821(7) Uani 1 1 d . . . . .
C43 C 0.8901(3) 0.3768(3) 0.9098(2) 0.0711(8) Uani 1 1 d . . . . .
H43 H 0.9081 0.3336 0.8570 0.085 Uiso 1 1 calc R U . . .
N7 N 0.8867(2) 0.3427(2) 0.9691(2) 0.0763(7) Uani 1 1 d . . . . .
C1 C 0.48170(16) 0.59616(14) 0.64191(13) 0.0308(4) Uani 1 1 d . . . . .
C2 C 0.36529(15) 0.59087(13) 0.66149(12) 0.0261(3) Uani 1 1 d . . . . .
C8 C 0.30608(16) 0.67386(13) 0.68441(13) 0.0295(4) Uani 1 1 d . . . . .
H8 H 0.3362 0.7295 0.6825 0.035 Uiso 1 1 calc R U . . .
C7 C 0.20212(16) 0.67419(13) 0.71007(13) 0.0300(4) Uani 1 1 d . . . . .
C9 C 0.0770(2) 0.79599(18) 0.7873(2) 0.0549(6) Uani 1 1 d . . . . .
C10 C 0.0345(3) 0.8931(2) 0.7947(3) 0.0825(10) Uani 1 1 d . . . . .
H10A H 0.0956 0.9314 0.7890 0.099 Uiso 1 1 calc R U . . .
H10B H -0.0339 0.8789 0.7451 0.099 Uiso 1 1 calc R U . . .
C6 C 0.15592(16) 0.59016(13) 0.71123(13) 0.0290(4) Uani 1 1 d . . . . .
H6 H 0.0871 0.5903 0.7291 0.035 Uiso 1 1 calc R U . . .
C4 C 0.21289(15) 0.50595(13) 0.68556(12) 0.0256(3) Uani 1 1 d . . . . .
C5 C 0.15573(16) 0.41341(13) 0.68033(13) 0.0294(4) Uani 1 1 d . . . . .
O3 O 0.06608(16) 0.41706(13) 0.70610(16) 0.0660(6) Uani 1 1 d . . . . .
C3 C 0.31798(15) 0.50653(13) 0.66168(12) 0.0263(3) Uani 1 1 d . . . . .
H3 H 0.3567 0.4507 0.6458 0.032 Uiso 1 1 calc R U . . .
C33 C 0.85962(17) 0.67451(14) 0.57175(13) 0.0309(4) Uani 1 1 d . . . . .
H33 H 0.8559 0.7393 0.5809 0.037 Uiso 1 1 calc R U . . .
C34 C 0.94498(17) 0.62433(14) 0.53375(13) 0.0318(4) Uani 1 1 d . . . . .
H34 H 0.9972 0.6554 0.5176 0.038 Uiso 1 1 calc R U . . .
C35 C 0.95342(15) 0.52761(13) 0.51951(11) 0.0248(3) Uani 1 1 d . . . . .
C36 C 0.87055(17) 0.48469(14) 0.54290(14) 0.0335(4) Uani 1 1 d . . . . .
H36 H 0.8716 0.4196 0.5335 0.040 Uiso 1 1 calc R U . . .
C37 C 0.78697(18) 0.53887(14) 0.58006(14) 0.0340(4) Uani 1 1 d . . . . .
H37 H 0.7318 0.5087 0.5948 0.041 Uiso 1 1 calc R U . . .
C12 C 0.66180(16) 0.91486(13) 0.70005(12) 0.0273(4) Uani 1 1 d . . . . .
C13 C 0.70165(15) 1.00901(12) 0.69967(12) 0.0249(3) Uani 1 1 d . . . . .
C14 C 0.80129(15) 1.01633(13) 0.67102(12) 0.0260(3) Uani 1 1 d . . . . .
H14A H 0.8451 0.9637 0.6539 0.031 Uiso 1 1 calc R U . . .
C15 C 0.83507(15) 1.10265(13) 0.66814(12) 0.0260(3) Uani 1 1 d . . . . .
C17 C 0.76899(17) 1.18101(13) 0.69361(12) 0.0290(4) Uani 1 1 d . . . . .
H17 H 0.7909 1.2383 0.6907 0.035 Uiso 1 1 calc R U . . .
C18 C 0.67012(16) 1.17444(13) 0.72342(12) 0.0280(4) Uani 1 1 d . . . . .
C20 C 0.5511(2) 1.28889(18) 0.81414(19) 0.0525(6) Uani 1 1 d . . . . .
C21 C 0.4877(3) 1.3782(2) 0.8234(2) 0.0752(9) Uani 1 1 d D . . . .
H21A H 0.4513 1.3713 0.7639 0.090 Uiso 0.630(4) 1 calc R U P A 1
H21B H 0.4255 1.3793 0.8522 0.090 Uiso 0.630(4) 1 calc R U P A 1
H21C H 0.5257 1.4146 0.8000 0.090 Uiso 0.370(4) 1 calc R U P A 2
H21D H 0.4076 1.3551 0.7862 0.090 Uiso 0.370(4) 1 calc R U P A 2
C19 C 0.63638(16) 1.08827(13) 0.72651(12) 0.0271(4) Uani 1 1 d . . . . .
H19 H 0.5706 1.0835 0.7464 0.033 Uiso 1 1 calc R U . . .
C16 C 0.94501(16) 1.11355(14) 0.64040(12) 0.0294(4) Uani 1 1 d . . . . .
C42 C 1.27538(17) 1.03141(14) 0.56764(13) 0.0308(4) Uani 1 1 d . . . . .
H42 H 1.2190 0.9995 0.5797 0.037 Uiso 1 1 calc R U . . .
C41 C 1.36628(17) 0.98098(14) 0.53742(13) 0.0310(4) Uani 1 1 d . . . . .
H41 H 1.3709 0.9172 0.5311 0.037 Uiso 1 1 calc R U . . .
C40 C 1.45034(15) 1.02577(13) 0.51664(11) 0.0246(3) Uani 1 1 d . . . . .
C39 C 1.43765(17) 1.12110(14) 0.52800(14) 0.0338(4) Uani 1 1 d . . . . .
H39 H 1.4910 1.1539 0.5142 0.041 Uiso 1 1 calc R U . . .
C38 C 1.34588(17) 1.16718(14) 0.55977(14) 0.0340(4) Uani 1 1 d . . . . .
H38 H 1.3396 1.2312 0.5674 0.041 Uiso 1 1 calc R U . . .
O7 O 0.57999(14) 0.91032(11) 0.73205(12) 0.0461(4) Uani 1 1 d . . . . .
C27 C 0.7730(2) 0.66842(18) 0.81744(15) 0.0464(6) Uani 1 1 d . . . . .
H27 H 0.7983 0.6162 0.7738 0.056 Uiso 1 1 calc R U . . .
C26 C 0.7886(2) 0.67208(18) 0.90155(15) 0.0490(6) Uani 1 1 d . . . . .
H26 H 0.8220 0.6223 0.9128 0.059 Uiso 1 1 calc R U . . .
C25 C 0.75439(19) 0.74969(15) 0.96842(13) 0.0369(4) Uani 1 1 d . . . . .
C24 C 0.7075(3) 0.82218(19) 0.94696(16) 0.0589(7) Uani 1 1 d . . . . .
H24 H 0.6860 0.8773 0.9903 0.071 Uiso 1 1 calc R U . . .
C23 C 0.6930(3) 0.81224(19) 0.86128(16) 0.0554(7) Uani 1 1 d . . . . .
H23 H 0.6602 0.8611 0.8481 0.066 Uiso 1 1 calc R U . . .
C28 C 0.76831(19) 0.75665(16) 1.05952(13) 0.0366(4) Uani 1 1 d . . . . .
C32 C 0.8140(3) 0.68433(18) 1.08167(16) 0.0536(7) Uani 1 1 d . . . . .
H32 H 0.8342 0.6282 1.0385 0.064 Uiso 1 1 calc R U . . .
C31 C 0.8293(3) 0.69619(18) 1.16806(16) 0.0529(6) Uani 1 1 d . . . . .
H31 H 0.8613 0.6473 1.1816 0.064 Uiso 1 1 calc R U . . .
C30 C 0.7536(3) 0.84052(19) 1.21078(15) 0.0549(7) Uani 1 1 d . . . . .
H30 H 0.7302 0.8941 1.2543 0.066 Uiso 1 1 calc R U . . .
C29 C 0.7371(3) 0.8356(2) 1.12648(16) 0.0578(7) Uani 1 1 d . . . . .
H29 H 0.7049 0.8858 1.1151 0.069 Uiso 1 1 calc R U . . .
C47 C 0.5837(4) 0.2540(3) 0.0621(3) 0.0993(13) Uani 1 1 d . . . . .
H47A H 0.5445 0.2778 0.1094 0.149 Uiso 1 1 calc R U . . .
H47B H 0.5342 0.2545 0.0094 0.149 Uiso 1 1 calc R U . . .
H47C H 0.6562 0.2959 0.0808 0.149 Uiso 1 1 calc R U . . .
C44 C 0.9001(4) 0.2403(3) 0.9472(3) 0.1112(15) Uani 1 1 d . . . . .
H44A H 0.8249 0.2046 0.9341 0.167 Uiso 1 1 calc R U . . .
H44B H 0.9529 0.2369 0.9973 0.167 Uiso 1 1 calc R U . . .
H44C H 0.9315 0.2116 0.8958 0.167 Uiso 1 1 calc R U . . .
C48 C 0.6388(5) 0.0938(3) -0.0421(3) 0.1167(17) Uani 1 1 d . . . . .
H48A H 0.7216 0.0890 -0.0299 0.175 Uiso 1 1 calc R U . . .
H48B H 0.6191 0.1243 -0.0812 0.175 Uiso 1 1 calc R U . . .
H48C H 0.5957 0.0290 -0.0704 0.175 Uiso 1 1 calc R U . . .
C45 C 0.8591(5) 0.4063(4) 1.0518(3) 0.1174(16) Uani 1 1 d . . . . .
H45A H 0.8915 0.4730 1.0714 0.176 Uiso 1 1 calc R U . . .
H45B H 0.8920 0.3856 1.0968 0.176 Uiso 1 1 calc R U . . .
H45C H 0.7752 0.4027 1.0424 0.176 Uiso 1 1 calc R U . . .
C11 C 0.0038(5) 0.9524(3) 0.8788(4) 0.135(2) Uani 1 1 d . . . . .
H11A H 0.0742 0.9807 0.9268 0.203 Uiso 1 1 calc R U . . .
H11B H -0.0447 0.9114 0.8910 0.203 Uiso 1 1 calc R U . . .
H11C H -0.0384 1.0042 0.8738 0.203 Uiso 1 1 calc R U . . .
C22A C 0.5629(7) 1.4703(4) 0.8741(6) 0.120(3) Uani 0.630(4) 1 d . . P A 1
H22A H 0.6016 1.4767 0.9324 0.180 Uiso 0.630(4) 1 calc R U P A 1
H22B H 0.5168 1.5236 0.8805 0.180 Uiso 0.630(4) 1 calc R U P A 1
H22C H 0.6208 1.4722 0.8433 0.180 Uiso 0.630(4) 1 calc R U P A 1
C22B C 0.4840(15) 1.4456(9) 0.9144(7) 0.127(6) Uani 0.370(4) 1 d D . P A 2
H22D H 0.4376 1.4131 0.9356 0.190 Uiso 0.370(4) 1 calc R U P A 2
H22E H 0.4496 1.5027 0.9145 0.190 Uiso 0.370(4) 1 calc R U P A 2
H22F H 0.5625 1.4656 0.9529 0.190 Uiso 0.370(4) 1 calc R U P A 2
O14A O 0.8158(2) 1.1769(2) 0.4094(2) 0.0608(10) Uani 0.630(4) 1 d . . P A 1
O14B O 0.8547(4) 1.2481(4) 0.5089(4) 0.0600(17) Uani 0.370(4) 1 d . . P A 2
H12O H 1.0404 1.0934 0.4502 0.090 Uiso 1 1 d . U . . .
H16A H 0.3000 0.5936 0.3104 0.090 Uiso 1 1 d . U . . .
H15B H 0.0757 0.5653 0.2645 0.090 Uiso 1 1 d . U . . .
H15A H 0.1239 0.5405 0.1939 0.090 Uiso 1 1 d . U . . .
H17B H 0.3709 0.6995 0.4617 0.090 Uiso 1 1 d . U . . .
H16B H 0.4002 0.5749 0.3364 0.090 Uiso 1 1 d . U . . .
H17O H 0.4073 0.7221 0.5556 0.090 Uiso 1 1 d . U . . .
H18A H 0.4221 0.9373 0.7310 0.090 Uiso 1 1 d . U . . .
H18B H 0.2847 0.9165 0.7058 0.090 Uiso 1 1 d . U . . .
H11O H 0.9787 1.1692 0.4687 0.090 Uiso 1 1 d . U . . .


_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 O6 1.9373(13) . ?
Zn1 O1 1.9446(14) . ?
Zn1 N5 2.0264(15) . ?
Zn1 N3 2.0539(17) . ?
Zn2 O4 1.9871(13) 1_665 ?
Zn2 O8 1.9925(14) . ?
Zn2 N6 2.0970(15) . ?
Zn2 O11 2.2007(15) . ?
Zn2 N4 2.2311(17) 2_777 ?
O1 C1 1.286(2) . ?
O15 H15B 0.88000 . ?
O15 H15A 0.87000 . ?
O2 C1 1.228(2) . ?
O5 C9 1.192(4) . ?
O17 H17B 0.93000 . ?
O17 H17O 0.85000 . ?
O18 H18A 0.91000 . ?
O18 H18B 0.81000 . ?
O4 C5 1.270(2) . ?
O4 Zn2 1.9871(13) 1_445 ?
O6 C12 1.283(2) . ?
O10 C20 1.206(3) . ?
O8 C16 1.274(2) . ?
O11 H12O 0.85000 . ?
O11 H11O 0.85000 . ?
O9 C16 1.238(2) . ?
O16 H16A 0.83000 . ?
O16 H16B 0.83000 . ?
N1 C9 1.344(3) . ?
N1 C7 1.415(2) . ?
N1 H1 0.8600 . ?
N5 C33 1.342(2) . ?
N5 C37 1.343(2) . ?
N2 C20 1.345(3) . ?
N2 C18 1.415(2) . ?
N2 H2 0.8600 . ?
N4 C30 1.322(3) . ?
N4 C31 1.330(3) . ?
N4 Zn2 2.2311(17) 2_777 ?
N6 C42 1.336(2) . ?
N6 C38 1.340(2) . ?
N3 C27 1.325(3) . ?
N3 C23 1.333(3) . ?
N8 C46 1.317(4) . ?
N8 C47 1.460(4) . ?
N8 C48 1.461(5) . ?
C46 O13 1.210(4) . ?
C46 H46 0.9300 . ?
O12 C43 1.201(4) . ?
C43 N7 1.336(4) . ?
C43 H43 0.9300 . ?
N7 C45 1.440(5) . ?
N7 C44 1.453(5) . ?
C1 C2 1.494(2) . ?
C2 C8 1.393(2) . ?
C2 C3 1.394(2) . ?
C8 C7 1.393(3) . ?
C8 H8 0.9300 . ?
C7 C6 1.393(3) . ?
C9 C10 1.524(4) . ?
C10 C11 1.461(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C6 C4 1.393(2) . ?
C6 H6 0.9300 . ?
C4 C3 1.391(2) . ?
C4 C5 1.511(2) . ?
C5 O3 1.228(2) . ?
C3 H3 0.9300 . ?
C33 C34 1.378(3) . ?
C33 H33 0.9300 . ?
C34 C35 1.389(2) . ?
C34 H34 0.9300 . ?
C35 C36 1.391(2) . ?
C35 C35 1.490(3) 2_766 ?
C36 C37 1.378(3) . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?
C12 O7 1.229(2) . ?
C12 C13 1.504(2) . ?
C13 C14 1.393(2) . ?
C13 C19 1.396(2) . ?
C14 C15 1.392(2) . ?
C14 H14A 0.9300 . ?
C15 C17 1.391(3) . ?
C15 C16 1.510(2) . ?
C17 C18 1.394(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.391(2) . ?
C20 C21 1.520(3) . ?
C21 C22A 1.434(7) . ?
C21 C22B 1.456(9) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 H21C 0.9700 . ?
C21 H21D 0.9700 . ?
C19 H19 0.9300 . ?
C42 C41 1.388(3) . ?
C42 H42 0.9300 . ?
C41 C40 1.390(3) . ?
C41 H41 0.9300 . ?
C40 C39 1.389(3) . ?
C40 C40 1.497(3) 2_876 ?
C39 C38 1.381(3) . ?
C39 H39 0.9300 . ?
C38 H38 0.9300 . ?
C27 C26 1.389(3) . ?
C27 H27 0.9300 . ?
C26 C25 1.381(3) . ?
C26 H26 0.9300 . ?
C25 C24 1.389(3) . ?
C25 C28 1.490(3) . ?
C24 C23 1.380(3) . ?
C24 H24 0.9300 . ?
C23 H23 0.9300 . ?
C28 C29 1.375(3) . ?
C28 C32 1.388(3) . ?
C32 C31 1.381(3) . ?
C32 H32 0.9300 . ?
C31 H31 0.9300 . ?
C30 C29 1.383(3) . ?
C30 H30 0.9300 . ?
C29 H29 0.9300 . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
C45 H45A 0.9600 . ?
C45 H45B 0.9600 . ?
C45 H45C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C22A H22A 0.9600 . ?
C22A H22B 0.9600 . ?
C22A H22C 0.9600 . ?
C22B H22D 0.9600 . ?
C22B H22E 0.9600 . ?
C22B H22F 0.9600 . ?

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
O6 Zn1 O1 117.58(6) . . ?
O6 Zn1 N5 99.66(6) . . ?
O1 Zn1 N5 117.85(6) . . ?
O6 Zn1 N3 110.05(7) . . ?
O1 Zn1 N3 102.00(7) . . ?
N5 Zn1 N3 109.77(7) . . ?
O4 Zn2 O8 117.93(6) 1_665 . ?
O4 Zn2 N6 97.24(6) 1_665 . ?
O8 Zn2 N6 144.65(6) . . ?
O4 Zn2 O11 95.56(6) 1_665 . ?
O8 Zn2 O11 88.50(6) . . ?
N6 Zn2 O11 84.43(6) . . ?
O4 Zn2 N4 96.57(6) 1_665 2_777 ?
O8 Zn2 N4 85.37(7) . 2_777 ?
N6 Zn2 N4 94.54(6) . 2_777 ?
O11 Zn2 N4 167.86(6) . 2_777 ?
C1 O1 Zn1 116.48(12) . . ?
H15B O15 H15A 102.00 . . ?
H17B O17 H17O 108.00 . . ?
H18A O18 H18B 132.00 . . ?
C5 O4 Zn2 121.43(12) . 1_445 ?
C12 O6 Zn1 118.26(12) . . ?
C16 O8 Zn2 110.24(12) . . ?
Zn2 O11 H12O 115.00 . . ?
Zn2 O11 H11O 118.00 . . ?
H12O O11 H11O 102.00 . . ?
H16A O16 H16B 96.00 . . ?
C9 N1 C7 128.2(2) . . ?
C9 N1 H1 115.9 . . ?
C7 N1 H1 115.9 . . ?
C33 N5 C37 117.70(15) . . ?
C33 N5 Zn1 118.91(12) . . ?
C37 N5 Zn1 122.95(12) . . ?
C20 N2 C18 126.80(18) . . ?
C20 N2 H2 116.6 . . ?
C18 N2 H2 116.6 . . ?
C30 N4 C31 116.28(18) . . ?
C30 N4 Zn2 124.97(15) . 2_777 ?
C31 N4 Zn2 117.57(14) . 2_777 ?
C42 N6 C38 117.39(16) . . ?
C42 N6 Zn2 125.36(13) . . ?
C38 N6 Zn2 117.24(12) . . ?
C27 N3 C23 117.37(18) . . ?
C27 N3 Zn1 123.06(14) . . ?
C23 N3 Zn1 119.14(14) . . ?
C46 N8 C47 122.0(3) . . ?
C46 N8 C48 119.5(3) . . ?
C47 N8 C48 118.5(3) . . ?
O13 C46 N8 126.9(3) . . ?
O13 C46 H46 116.5 . . ?
N8 C46 H46 116.5 . . ?
O12 C43 N7 126.4(3) . . ?
O12 C43 H43 116.8 . . ?
N7 C43 H43 116.8 . . ?
C43 N7 C45 119.2(3) . . ?
C43 N7 C44 120.5(3) . . ?
C45 N7 C44 120.1(4) . . ?
O2 C1 O1 122.94(17) . . ?
O2 C1 C2 120.66(16) . . ?
O1 C1 C2 116.27(16) . . ?
C8 C2 C3 119.58(16) . . ?
C8 C2 C1 119.02(16) . . ?
C3 C2 C1 121.32(16) . . ?
C7 C8 C2 120.55(16) . . ?
C7 C8 H8 119.7 . . ?
C2 C8 H8 119.7 . . ?
C8 C7 C6 119.66(16) . . ?
C8 C7 N1 116.90(17) . . ?
C6 C7 N1 123.43(17) . . ?
O5 C9 N1 122.9(2) . . ?
O5 C9 C10 123.5(3) . . ?
N1 C9 C10 113.5(3) . . ?
C11 C10 C9 113.8(4) . . ?
C11 C10 H10A 108.8 . . ?
C9 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C7 C6 C4 119.94(16) . . ?
C7 C6 H6 120.0 . . ?
C4 C6 H6 120.0 . . ?
C3 C4 C6 120.23(16) . . ?
C3 C4 C5 120.96(15) . . ?
C6 C4 C5 118.75(16) . . ?
O3 C5 O4 124.34(17) . . ?
O3 C5 C4 119.02(17) . . ?
O4 C5 C4 116.64(16) . . ?
C4 C3 C2 119.99(16) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
N5 C33 C34 122.40(17) . . ?
N5 C33 H33 118.8 . . ?
C34 C33 H33 118.8 . . ?
C33 C34 C35 120.32(17) . . ?
C33 C34 H34 119.8 . . ?
C35 C34 H34 119.8 . . ?
C34 C35 C36 116.89(16) . . ?
C34 C35 C35 121.4(2) . 2_766 ?
C36 C35 C35 121.7(2) . 2_766 ?
C37 C36 C35 119.80(17) . . ?
C37 C36 H36 120.1 . . ?
C35 C36 H36 120.1 . . ?
N5 C37 C36 122.85(17) . . ?
N5 C37 H37 118.6 . . ?
C36 C37 H37 118.6 . . ?
O7 C12 O6 123.39(17) . . ?
O7 C12 C13 120.75(16) . . ?
O6 C12 C13 115.86(15) . . ?
C14 C13 C19 120.32(16) . . ?
C14 C13 C12 120.34(15) . . ?
C19 C13 C12 119.33(15) . . ?
C15 C14 C13 119.81(16) . . ?
C15 C14 H14A 120.1 . . ?
C13 C14 H14A 120.1 . . ?
C17 C15 C14 119.82(16) . . ?
C17 C15 C16 119.43(16) . . ?
C14 C15 C16 120.72(16) . . ?
C15 C17 C18 120.54(16) . . ?
C15 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 119.70(16) . . ?
C19 C18 N2 122.24(17) . . ?
C17 C18 N2 118.04(16) . . ?
O10 C20 N2 122.7(2) . . ?
O10 C20 C21 122.6(2) . . ?
N2 C20 C21 114.7(2) . . ?
C22A C21 C20 113.7(4) . . ?
C22B C21 C20 115.4(6) . . ?
C22A C21 H21A 108.8 . . ?
C20 C21 H21A 108.8 . . ?
C22A C21 H21B 108.8 . . ?
C20 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
C22B C21 H21C 108.4 . . ?
C20 C21 H21C 108.4 . . ?
C22B C21 H21D 108.4 . . ?
C20 C21 H21D 108.4 . . ?
H21C C21 H21D 107.5 . . ?
C18 C19 C13 119.79(16) . . ?
C18 C19 H19 120.1 . . ?
C13 C19 H19 120.1 . . ?
O9 C16 O8 123.33(17) . . ?
O9 C16 C15 120.84(17) . . ?
O8 C16 C15 115.81(16) . . ?
N6 C42 C41 122.85(17) . . ?
N6 C42 H42 118.6 . . ?
C41 C42 H42 118.6 . . ?
C42 C41 C40 119.98(17) . . ?
C42 C41 H41 120.0 . . ?
C40 C41 H41 120.0 . . ?
C39 C40 C41 116.67(16) . . ?
C39 C40 C40 121.3(2) . 2_876 ?
C41 C40 C40 122.0(2) . 2_876 ?
C38 C39 C40 120.05(17) . . ?
C38 C39 H39 120.0 . . ?
C40 C39 H39 120.0 . . ?
N6 C38 C39 123.02(17) . . ?
N6 C38 H38 118.5 . . ?
C39 C38 H38 118.5 . . ?
N3 C27 C26 123.0(2) . . ?
N3 C27 H27 118.5 . . ?
C26 C27 H27 118.5 . . ?
C25 C26 C27 120.0(2) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C26 C25 C24 116.57(19) . . ?
C26 C25 C28 122.09(19) . . ?
C24 C25 C28 121.33(19) . . ?
C23 C24 C25 119.9(2) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
N3 C23 C24 123.1(2) . . ?
N3 C23 H23 118.4 . . ?
C24 C23 H23 118.4 . . ?
C29 C28 C32 116.4(2) . . ?
C29 C28 C25 121.7(2) . . ?
C32 C28 C25 121.96(19) . . ?
C31 C32 C28 119.6(2) . . ?
C31 C32 H32 120.2 . . ?
C28 C32 H32 120.2 . . ?
N4 C31 C32 123.8(2) . . ?
N4 C31 H31 118.1 . . ?
C32 C31 H31 118.1 . . ?
N4 C30 C29 123.8(2) . . ?
N4 C30 H30 118.1 . . ?
C29 C30 H30 118.1 . . ?
C28 C29 C30 120.0(2) . . ?
C28 C29 H29 120.0 . . ?
C30 C29 H29 120.0 . . ?
N8 C47 H47A 109.5 . . ?
N8 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
N8 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
N7 C44 H44A 109.5 . . ?
N7 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
N7 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
N8 C48 H48A 109.5 . . ?
N8 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
N8 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
N7 C45 H45A 109.5 . . ?
N7 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
N7 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C21 C22A H22A 109.5 . . ?
C21 C22A H22B 109.5 . . ?
H22A C22A H22B 109.5 . . ?
C21 C22A H22C 109.5 . . ?
H22A C22A H22C 109.5 . . ?
H22B C22A H22C 109.5 . . ?
C21 C22B H22D 109.5 . . ?
C21 C22B H22E 109.5 . . ?
H22D C22B H22E 109.5 . . ?
C21 C22B H22F 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 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
C47 N8 C46 O13 -175.1(3) . . . . ?
C48 N8 C46 O13 2.4(6) . . . . ?
O12 C43 N7 C45 0.1(6) . . . . ?
O12 C43 N7 C44 174.7(4) . . . . ?
Zn1 O1 C1 O2 -27.7(3) . . . . ?
Zn1 O1 C1 C2 148.31(13) . . . . ?
O2 C1 C2 C8 162.9(2) . . . . ?
O1 C1 C2 C8 -13.2(3) . . . . ?
O2 C1 C2 C3 -13.8(3) . . . . ?
O1 C1 C2 C3 170.08(17) . . . . ?
C3 C2 C8 C7 2.0(3) . . . . ?
C1 C2 C8 C7 -174.82(17) . . . . ?
C2 C8 C7 C6 -1.2(3) . . . . ?
C2 C8 C7 N1 -179.63(17) . . . . ?
C9 N1 C7 C8 -153.0(2) . . . . ?
C9 N1 C7 C6 28.6(3) . . . . ?
C7 N1 C9 O5 -1.3(5) . . . . ?
C7 N1 C9 C10 179.6(2) . . . . ?
O5 C9 C10 C11 26.2(6) . . . . ?
N1 C9 C10 C11 -154.8(4) . . . . ?
C8 C7 C6 C4 -0.9(3) . . . . ?
N1 C7 C6 C4 177.44(18) . . . . ?
C7 C6 C4 C3 2.2(3) . . . . ?
C7 C6 C4 C5 -175.15(17) . . . . ?
Zn2 O4 C5 O3 5.0(3) 1_445 . . . ?
Zn2 O4 C5 C4 -174.37(12) 1_445 . . . ?
C3 C4 C5 O3 176.5(2) . . . . ?
C6 C4 C5 O3 -6.2(3) . . . . ?
C3 C4 C5 O4 -4.1(3) . . . . ?
C6 C4 C5 O4 173.25(17) . . . . ?
C6 C4 C3 C2 -1.4(3) . . . . ?
C5 C4 C3 C2 175.88(16) . . . . ?
C8 C2 C3 C4 -0.7(3) . . . . ?
C1 C2 C3 C4 176.04(17) . . . . ?
C37 N5 C33 C34 -1.6(3) . . . . ?
Zn1 N5 C33 C34 171.10(15) . . . . ?
N5 C33 C34 C35 -0.3(3) . . . . ?
C33 C34 C35 C36 1.8(3) . . . . ?
C33 C34 C35 C35 -178.6(2) . . . 2_766 ?
C34 C35 C36 C37 -1.3(3) . . . . ?
C35 C35 C36 C37 179.0(2) 2_766 . . . ?
C33 N5 C37 C36 2.0(3) . . . . ?
Zn1 N5 C37 C36 -170.32(16) . . . . ?
C35 C36 C37 N5 -0.6(3) . . . . ?
Zn1 O6 C12 O7 -0.8(3) . . . . ?
Zn1 O6 C12 C13 178.30(12) . . . . ?
O7 C12 C13 C14 173.96(19) . . . . ?
O6 C12 C13 C14 -5.2(3) . . . . ?
O7 C12 C13 C19 -7.4(3) . . . . ?
O6 C12 C13 C19 173.46(17) . . . . ?
C19 C13 C14 C15 -0.8(3) . . . . ?
C12 C13 C14 C15 177.88(16) . . . . ?
C13 C14 C15 C17 -0.2(3) . . . . ?
C13 C14 C15 C16 177.87(16) . . . . ?
C14 C15 C17 C18 1.0(3) . . . . ?
C16 C15 C17 C18 -177.06(17) . . . . ?
C15 C17 C18 C19 -0.9(3) . . . . ?
C15 C17 C18 N2 -179.36(17) . . . . ?
C20 N2 C18 C19 37.1(3) . . . . ?
C20 N2 C18 C17 -144.4(2) . . . . ?
C18 N2 C20 O10 0.2(5) . . . . ?
C18 N2 C20 C21 -179.5(2) . . . . ?
O10 C20 C21 C22A 97.1(6) . . . . ?
N2 C20 C21 C22A -83.2(6) . . . . ?
O10 C20 C21 C22B 32.1(9) . . . . ?
N2 C20 C21 C22B -148.2(8) . . . . ?
C17 C18 C19 C13 -0.1(3) . . . . ?
N2 C18 C19 C13 178.32(17) . . . . ?
C14 C13 C19 C18 0.9(3) . . . . ?
C12 C13 C19 C18 -177.75(16) . . . . ?
Zn2 O8 C16 O9 -7.4(2) . . . . ?
Zn2 O8 C16 C15 170.73(12) . . . . ?
C17 C15 C16 O9 -178.73(18) . . . . ?
C14 C15 C16 O9 3.2(3) . . . . ?
C17 C15 C16 O8 3.0(3) . . . . ?
C14 C15 C16 O8 -175.03(17) . . . . ?
C38 N6 C42 C41 1.9(3) . . . . ?
Zn2 N6 C42 C41 -179.38(14) . . . . ?
N6 C42 C41 C40 -1.6(3) . . . . ?
C42 C41 C40 C39 0.1(3) . . . . ?
C42 C41 C40 C40 -179.7(2) . . . 2_876 ?
C41 C40 C39 C38 0.9(3) . . . . ?
C40 C40 C39 C38 -179.3(2) 2_876 . . . ?
C42 N6 C38 C39 -0.8(3) . . . . ?
Zn2 N6 C38 C39 -179.61(16) . . . . ?
C40 C39 C38 N6 -0.6(3) . . . . ?
C23 N3 C27 C26 2.8(4) . . . . ?
Zn1 N3 C27 C26 -169.6(2) . . . . ?
N3 C27 C26 C25 -1.4(4) . . . . ?
C27 C26 C25 C24 -1.3(4) . . . . ?
C27 C26 C25 C28 179.5(2) . . . . ?
C26 C25 C24 C23 2.5(4) . . . . ?
C28 C25 C24 C23 -178.3(3) . . . . ?
C27 N3 C23 C24 -1.6(4) . . . . ?
Zn1 N3 C23 C24 171.2(2) . . . . ?
C25 C24 C23 N3 -1.1(5) . . . . ?
C26 C25 C28 C29 178.1(2) . . . . ?
C24 C25 C28 C29 -1.0(4) . . . . ?
C26 C25 C28 C32 -1.5(4) . . . . ?
C24 C25 C28 C32 179.4(3) . . . . ?
C29 C28 C32 C31 -2.1(4) . . . . ?
C25 C28 C32 C31 177.5(3) . . . . ?
C30 N4 C31 C32 1.2(4) . . . . ?
Zn2 N4 C31 C32 -167.0(2) 2_777 . . . ?
C28 C32 C31 N4 1.1(5) . . . . ?
C31 N4 C30 C29 -2.4(4) . . . . ?
Zn2 N4 C30 C29 164.8(2) 2_777 . . . ?
C32 C28 C29 C30 1.0(4) . . . . ?
C25 C28 C29 C30 -178.6(3) . . . . ?
N4 C30 C29 C28 1.3(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O14A 0.86 2.26 3.068(4) 155.6 2_676
N2 H2 O16 0.86 2.09 2.934(2) 165.4 2_676
C6 H6 O5 0.93 2.43 2.924(3) 113.5 .
O11 H12O O9 0.85000 1.89000 2.732(2) 168.00 2_776
O16 H16A O15 0.83000 1.87000 2.687(3) 168.00 .
O15 H15B O3 0.88000 1.84000 2.717(2) 173.00 2_566
O15 H15A O12 0.87000 1.94000 2.785(3) 163.40(17) 2_666
O17 H17B O16 0.93000 1.82000 2.747(3) 173.00 .
O16 H16B O2 0.83000 1.93000 2.716(2) 156.28(14) 2_666
O17 H17O O1 0.85000 1.97000 2.821(2) 173.00 .
O18 H18A O7 0.91000 1.91000 2.798(3) 168.00 .
O18 H18B O14A 0.81000 1.939(4) 2.681(4) 151.70(18) 2_676
O11 H11O O14A 0.85000 1.985(3) 2.820(3) 167.79(14) .
O11 H11O O14B 0.85000 1.954(5) 2.704(5) 146.8(2) .

_refine_diff_density_max         0.976
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.090

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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 1490730'
_audit_update_record             
;
2016-07-05 deposited with the CCDC.
2016-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 Cd N2 O6'
_chemical_formula_weight         420.69

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'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           110
_space_group_name_H-M_alt        'I 41 c d'
_space_group_name_Hall           'I 4bw -2c'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+1/2, x, z+3/4'
'y+1/2, -x, z+3/4'
'-x, -y, z'
'-x, y, z+1/2'
'x, -y, z+1/2'
'-y+1/2, -x, z+1/4'
'y+1/2, x, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-y+1, x+1/2, z+5/4'
'y+1, -x+1/2, z+5/4'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z+1'
'x+1/2, -y+1/2, z+1'
'-y+1, -x+1/2, z+3/4'
'y+1, x+1/2, z+3/4'

_cell_length_a                   24.9839(7)
_cell_length_b                   24.9839(7)
_cell_length_c                   10.2525(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6399.6(4)
_cell_formula_units_Z            16
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9601
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      25.36

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.747
_exptl_crystal_F_000             3360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    1.396
_shelx_estimated_absorpt_T_min   0.641
_shelx_estimated_absorpt_T_max   0.777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6
_exptl_absorpt_correction_T_max  0.7
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35966
_diffrn_reflns_av_unetI/netI     0.0109
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_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         2.306
_diffrn_reflns_theta_max         25.363
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2916
_reflns_number_gt                2839
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.868
_reflns_Friedel_fraction_max     0.985
_reflns_Friedel_fraction_full    0.985

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1999)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury CSD 3.5.1, 2008'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0449P)²+8.2789P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1310 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.048(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2916
_refine_ls_number_parameters     214
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0262
_refine_ls_wR_factor_ref         0.0639
_refine_ls_wR_factor_gt          0.0628
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.067
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.8493(2) 0.1679(2) 0.9726(4) 0.0564(13) Uani 1 1 d . . . . .
C7 C 0.8234(2) 0.1741(2) 0.8685(6) 0.0335(11) Uani 1 1 d . . . . .
C6 C 0.8515(2) 0.1602(2) 0.7431(5) 0.0275(10) Uani 1 1 d . . . . .
Cd1 Cd 0.81325(2) 0.29496(2) 0.38441(6) 0.02663(12) Uani 1 1 d . . . . .
O2 O 0.85567(18) 0.14767(18) 0.2806(4) 0.0438(10) Uani 1 1 d . . . . .
O4 O 0.77614(19) 0.19091(18) 0.8641(5) 0.0519(11) Uani 1 1 d . . . . .
O5 O 1.00592(17) 0.08105(19) 0.4485(4) 0.0502(10) Uani 1 1 d . . . . .
O1 O 0.79910(13) 0.20527(14) 0.3653(4) 0.0290(8) Uani 1 1 d . . . . .
N1 N 0.97751(18) 0.0915(2) 0.6569(4) 0.0401(11) Uani 1 1 d D . . . .
C1 C 0.83666(18) 0.17089(18) 0.3775(6) 0.0286(9) Uani 1 1 d . . . . .
O6 O 0.90300(16) 0.26431(17) 0.3782(7) 0.0680(13) Uani 1 1 d . . . . .
N2 N 0.9902(2) 0.2603(3) 0.4221(12) 0.109(4) Uani 1 1 d . . . . .
C8 C 0.83011(17) 0.17312(17) 0.6225(5) 0.0276(8) Uani 1 1 d . . . . .
H8 H 0.7980 0.1918 0.6166 0.033 Uiso 1 1 calc R U . . .
C5 C 0.9000(2) 0.1330(2) 0.7512(5) 0.0297(11) Uani 1 1 d . . . . .
H5 H 0.9142 0.1248 0.8327 0.036 Uiso 1 1 calc R U . . .
C2 C 0.8573(2) 0.1578(2) 0.5109(5) 0.0276(11) Uani 1 1 d . . . . .
C4 C 0.92764(16) 0.11787(17) 0.6392(6) 0.0288(8) Uani 1 1 d . . . . .
C9 C 1.0138(2) 0.0767(2) 0.5644(5) 0.0361(11) Uani 1 1 d . . . . .
C10 C 1.0640(2) 0.0520(3) 0.6212(8) 0.0532(15) Uani 1 1 d . . . . .
H10A H 1.0852 0.0798 0.6622 0.064 Uiso 1 1 calc R U . . .
H10B H 1.0539 0.0265 0.6883 0.064 Uiso 1 1 calc R U . . .
C3 C 0.9058(2) 0.1305(2) 0.5179(5) 0.0301(11) Uani 1 1 d . . . . .
H3 H 0.9235 0.1206 0.4419 0.036 Uiso 1 1 calc R U . . .
C11 C 1.0976(3) 0.0241(3) 0.5221(8) 0.0623(18) Uani 1 1 d . . . . .
H11A H 1.0751 0.0033 0.4657 0.094 Uiso 1 1 calc R U . . .
H11B H 1.1227 0.0010 0.5653 0.094 Uiso 1 1 calc R U . . .
H11C H 1.1168 0.0501 0.4714 0.094 Uiso 1 1 calc R U . . .
C12 C 0.9418(3) 0.2784(4) 0.4356(11) 0.080(3) Uani 1 1 d . . . . .
H12 H 0.9369 0.3053 0.4971 0.096 Uiso 1 1 calc R U . . .
C13 C 1.0004(6) 0.2187(7) 0.332(2) 0.194(11) Uani 1 1 d . . . . .
H13A H 0.9888 0.2295 0.2469 0.290 Uiso 1 1 calc R U . . .
H13B H 0.9812 0.1872 0.3583 0.290 Uiso 1 1 calc R U . . .
H13C H 1.0380 0.2111 0.3306 0.290 Uiso 1 1 calc R U . . .
C14 C 1.0366(6) 0.2812(10) 0.491(3) 0.240(13) Uani 1 1 d . . . . .
H14A H 1.0328 0.3192 0.5028 0.360 Uiso 1 1 calc R U . . .
H14B H 1.0684 0.2739 0.4420 0.360 Uiso 1 1 calc R U . . .
H14C H 1.0392 0.2643 0.5753 0.360 Uiso 1 1 calc R U . . .
H1N H 0.988(11) 0.079(9) 0.735(11) 0.360 Uiso 1 1 d D U . . .


_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
O3 C7 1.257(8) . ?
O3 Cd1 2.195(4) 3_565 ?
C7 O4 1.255(8) . ?
C7 C6 1.506(8) . ?
C6 C8 1.385(8) . ?
C6 C5 1.392(7) . ?
Cd1 O3 2.195(4) 10_543 ?
Cd1 O4 2.270(5) 12_654 ?
Cd1 O1 2.277(4) . ?
Cd1 O2 2.346(4) 10_544 ?
Cd1 O6 2.370(4) . ?
Cd1 O1 2.414(4) 10_544 ?
Cd1 C1 2.730(6) 10_544 ?
O2 C1 1.244(7) . ?
O2 Cd1 2.346(4) 3_564 ?
O4 Cd1 2.270(5) 12_655 ?
O5 C9 1.209(7) . ?
O1 C1 1.278(6) . ?
O1 Cd1 2.414(4) 3_564 ?
N1 C9 1.362(6) . ?
N1 C4 1.421(6) . ?
N1 H1N 0.90(3) . ?
C1 C2 1.498(8) . ?
C1 Cd1 2.730(6) 3_564 ?
O6 C12 1.187(9) . ?
N2 C12 1.298(10) . ?
N2 C14 1.457(18) . ?
N2 C13 1.413(19) . ?
C8 C2 1.384(8) . ?
C8 H8 0.9300 . ?
C5 C4 1.392(8) . ?
C5 H5 0.9300 . ?
C2 C3 1.393(7) . ?
C4 C3 1.394(8) . ?
C9 C10 1.516(7) . ?
C10 C11 1.490(10) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C3 H3 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
C7 O3 Cd1 107.3(4) . 3_565 ?
O4 C7 O3 123.8(5) . . ?
O4 C7 C6 119.0(5) . . ?
O3 C7 C6 117.2(4) . . ?
C8 C6 C5 120.2(5) . . ?
C8 C6 C7 121.9(5) . . ?
C5 C6 C7 117.9(5) . . ?
O3 Cd1 O4 92.58(19) 10_543 12_654 ?
O3 Cd1 O1 125.25(16) 10_543 . ?
O4 Cd1 O1 89.56(13) 12_654 . ?
O3 Cd1 O2 89.65(16) 10_543 10_544 ?
O4 Cd1 O2 111.57(17) 12_654 10_544 ?
O1 Cd1 O2 139.11(15) . 10_544 ?
O3 Cd1 O6 88.7(2) 10_543 . ?
O4 Cd1 O6 168.02(18) 12_654 . ?
O1 Cd1 O6 80.02(13) . . ?
O2 Cd1 O6 80.34(17) 10_544 . ?
O3 Cd1 O1 139.08(15) 10_543 10_544 ?
O4 Cd1 O1 83.96(17) 12_654 10_544 ?
O1 Cd1 O1 95.55(15) . 10_544 ?
O2 Cd1 O1 54.92(13) 10_544 10_544 ?
O6 Cd1 O1 102.8(2) . 10_544 ?
O3 Cd1 C1 115.00(17) 10_543 10_544 ?
O4 Cd1 C1 99.63(17) 12_654 10_544 ?
O1 Cd1 C1 118.47(15) . 10_544 ?
O2 Cd1 C1 27.04(15) 10_544 10_544 ?
O6 Cd1 C1 90.60(19) . 10_544 ?
O1 Cd1 C1 27.92(13) 10_544 10_544 ?
C1 O2 Cd1 94.0(3) . 3_564 ?
C7 O4 Cd1 167.1(4) . 12_655 ?
C1 O1 Cd1 122.6(3) . . ?
C1 O1 Cd1 89.9(3) . 3_564 ?
Cd1 O1 Cd1 106.23(16) . 3_564 ?
C9 N1 C4 128.3(5) . . ?
C9 N1 H1N 109(10) . . ?
C4 N1 H1N 122(10) . . ?
O2 C1 O1 121.1(5) . . ?
O2 C1 C2 119.7(4) . . ?
O1 C1 C2 119.2(5) . . ?
O2 C1 Cd1 59.0(3) . 3_564 ?
O1 C1 Cd1 62.2(3) . 3_564 ?
C2 C1 Cd1 175.3(3) . 3_564 ?
C12 O6 Cd1 131.6(6) . . ?
C12 N2 C14 124.5(13) . . ?
C12 N2 C13 119.5(11) . . ?
C14 N2 C13 116.0(13) . . ?
C6 C8 C2 118.9(4) . . ?
C6 C8 H8 120.5 . . ?
C2 C8 H8 120.5 . . ?
C4 C5 C6 121.0(5) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C3 C2 C8 121.3(5) . . ?
C3 C2 C1 116.9(5) . . ?
C8 C2 C1 121.8(5) . . ?
C5 C4 C3 118.7(4) . . ?
C5 C4 N1 117.1(5) . . ?
C3 C4 N1 124.2(5) . . ?
O5 C9 N1 123.5(5) . . ?
O5 C9 C10 123.2(5) . . ?
N1 C9 C10 113.2(5) . . ?
C11 C10 C9 113.3(6) . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C2 C3 C4 119.9(5) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O6 C12 N2 127.3(10) . . ?
O6 C12 H12 116.4 . . ?
N2 C12 H12 116.4 . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
Cd1 O3 C7 O4 3.6(7) 3_565 . . . ?
Cd1 O3 C7 C6 -176.4(4) 3_565 . . . ?
O4 C7 C6 C8 10.2(8) . . . . ?
O3 C7 C6 C8 -169.8(5) . . . . ?
O4 C7 C6 C5 -169.0(5) . . . . ?
O3 C7 C6 C5 11.0(8) . . . . ?
O3 C7 O4 Cd1 -59(2) . . . 12_655 ?
C6 C7 O4 Cd1 120.7(17) . . . 12_655 ?
Cd1 O2 C1 O1 -4.1(5) 3_564 . . . ?
Cd1 O2 C1 C2 174.7(4) 3_564 . . . ?
Cd1 O1 C1 O2 -105.3(5) . . . . ?
Cd1 O1 C1 O2 4.0(5) 3_564 . . . ?
Cd1 O1 C1 C2 75.8(5) . . . . ?
Cd1 O1 C1 C2 -174.9(4) 3_564 . . . ?
Cd1 O1 C1 Cd1 -109.3(4) . . . 3_564 ?
C5 C6 C8 C2 1.0(7) . . . . ?
C7 C6 C8 C2 -178.1(5) . . . . ?
C8 C6 C5 C4 -0.6(8) . . . . ?
C7 C6 C5 C4 178.6(5) . . . . ?
C6 C8 C2 C3 -0.9(7) . . . . ?
C6 C8 C2 C1 -179.4(5) . . . . ?
O2 C1 C2 C3 15.9(7) . . . . ?
O1 C1 C2 C3 -165.2(5) . . . . ?
O2 C1 C2 C8 -165.4(5) . . . . ?
O1 C1 C2 C8 13.5(7) . . . . ?
C6 C5 C4 C3 0.0(7) . . . . ?
C6 C5 C4 N1 178.4(5) . . . . ?
C9 N1 C4 C5 -174.2(6) . . . . ?
C9 N1 C4 C3 4.1(9) . . . . ?
C4 N1 C9 O5 -5.8(10) . . . . ?
C4 N1 C9 C10 176.9(5) . . . . ?
O5 C9 C10 C11 -11.2(9) . . . . ?
N1 C9 C10 C11 166.1(6) . . . . ?
C8 C2 C3 C4 0.3(8) . . . . ?
C1 C2 C3 C4 178.9(4) . . . . ?
C5 C4 C3 C2 0.2(7) . . . . ?
N1 C4 C3 C2 -178.1(5) . . . . ?
Cd1 O6 C12 N2 -177.2(7) . . . . ?
C14 N2 C12 O6 176.9(15) . . . . ?
C13 N2 C12 O6 -1.2(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C5 H5 O5 0.93 2.57 3.361(7) 143.6 5_755
C10 H10A O2 0.97 2.56 3.523(8) 175.6 5_755
C3 H3 O5 0.93 2.29 2.880(6) 121.3 .
C12 H12 O2 0.93 2.48 3.111(10) 124.8 10_544
C5 H5 O5 0.93 2.57 3.361(7) 143.6 5_755
C10 H10A O2 0.97 2.56 3.523(8) 175.6 5_755
C3 H3 O5 0.93 2.29 2.880(6) 121.3 .
C12 H12 O2 0.93 2.48 3.111(10) 124.8 10_544

_refine_diff_density_max         1.412
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.113

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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 1490731'
_audit_update_record             
;
2016-08-23 deposited with the CCDC.
2016-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H19 N3 O7 Zn'
_chemical_formula_sum            'C25 H19 N3 O7 Zn'
_chemical_formula_weight         538.80

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+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                   15.439(11)
_cell_length_b                   10.758(7)
_cell_length_c                   28.81(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.73(3)
_cell_angle_gamma                90
_cell_volume                     4785(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9841
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      26.27

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_F_000             2208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.078
_shelx_estimated_absorpt_T_min   0.711
_shelx_estimated_absorpt_T_max   0.900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7
_exptl_absorpt_correction_T_max  0.8
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26406
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.307
_diffrn_reflns_theta_max         25.442
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4408
_reflns_number_gt                3267
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury CSD 3.5.1, 2008'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1398P)²+45.7862P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4408
_refine_ls_number_parameters     380
_refine_ls_number_restraints     124
_refine_ls_R_factor_all          0.1224
_refine_ls_R_factor_gt           0.0956
_refine_ls_wR_factor_ref         0.2761
_refine_ls_wR_factor_gt          0.2488
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6345(6) 0.4311(10) 0.3272(3) 0.081(3) Uani 1 1 d . . . . .
H1 H 0.6914 0.4566 0.3320 0.097 Uiso 1 1 calc R U . . .
C2 C 0.6024(6) 0.4279(10) 0.2824(3) 0.077(3) Uani 1 1 d . . . . .
H2 H 0.6379 0.4490 0.2578 0.092 Uiso 1 1 calc R U . . .
C3 C 0.5192(5) 0.3941(8) 0.2742(3) 0.0597(18) Uani 1 1 d . . . . .
C4 C 0.4710(6) 0.3592(10) 0.3113(3) 0.082(3) Uani 1 1 d . . . . .
H4 H 0.4138 0.3339 0.3073 0.099 Uiso 1 1 calc R U . . .
C5 C 0.5090(6) 0.3621(11) 0.3552(3) 0.083(3) Uani 1 1 d . . . . .
H5 H 0.4761 0.3359 0.3802 0.100 Uiso 1 1 calc R U . . .
C6 C 0.5028(5) 0.2720(8) 0.4715(3) 0.065(2) Uani 1 1 d . . . . .
H6 H 0.4671 0.3414 0.4692 0.078 Uiso 1 1 calc R U . . .
C7 C 0.4686(5) 0.1661(8) 0.4876(3) 0.064(2) Uani 1 1 d . . . . .
H7 H 0.4110 0.1642 0.4968 0.077 Uiso 1 1 calc R U . . .
C8 C 0.5185(4) 0.0598(7) 0.4907(2) 0.0510(17) Uani 1 1 d . . . . .
C9 C 0.6028(5) 0.0703(8) 0.4772(3) 0.064(2) Uani 1 1 d . . . . .
H9 H 0.6391 0.0013 0.4787 0.077 Uiso 1 1 calc R U . . .
C10 C 0.6339(5) 0.1798(8) 0.4619(3) 0.067(2) Uani 1 1 d . . . . .
H10 H 0.6916 0.1838 0.4531 0.081 Uiso 1 1 calc R U . . .
C11 C 0.5245(5) 0.6367(8) 0.4202(3) 0.0629(19) Uani 1 1 d . U . . .
C12 C 0.5000(5) 0.7598(8) 0.4000(2) 0.0580(19) Uani 1 1 d . . . . .
C13 C 0.5585(5) 0.8279(8) 0.3747(3) 0.065(2) Uani 1 1 d . . . . .
H13 H 0.6131 0.7951 0.3690 0.077 Uiso 1 1 calc R U . . .
C14 C 0.5373(5) 0.9436(8) 0.3577(3) 0.0605(19) Uani 1 1 d . . . . .
C15 C 0.4576(5) 0.9939(8) 0.3673(3) 0.0593(19) Uani 1 1 d . . . . .
H15 H 0.4440 1.0738 0.3572 0.071 Uiso 1 1 calc R U . . .
C16 C 0.3973(4) 0.9256(7) 0.3919(2) 0.0516(17) Uani 1 1 d . . . . .
C17 C 0.4182(4) 0.8068(7) 0.4074(2) 0.0516(17) Uani 1 1 d . . . . .
H17 H 0.3771 0.7591 0.4226 0.062 Uiso 1 1 calc R U . . .
C18 C 0.6737(10) 1.0320(15) 0.3365(5) 0.064(5) Uani 0.519(18) 1 d D . P A 1
C19 C 0.7193(10) 1.1063(13) 0.3017(5) 0.064(5) Uani 0.519(18) 1 d DG U P A 1
C20 C 0.7940(12) 1.1660(17) 0.3174(4) 0.080(6) Uani 0.519(18) 1 d G U P A 1
H20 H 0.8115 1.1584 0.3483 0.096 Uiso 0.519(18) 1 calc R U P A 1
C21 C 0.8424(11) 1.237(2) 0.2869(6) 0.107(9) Uani 0.519(18) 1 d G U P A 1
H21 H 0.8924 1.2770 0.2974 0.128 Uiso 0.519(18) 1 calc R U P A 1
C22 C 0.8162(12) 1.248(2) 0.2408(6) 0.089(10) Uani 0.519(18) 1 d G U P A 1
H22 H 0.8487 1.2959 0.2204 0.107 Uiso 0.519(18) 1 calc R U P A 1
C23 C 0.7416(11) 1.1887(19) 0.2251(5) 0.077(6) Uani 0.519(18) 1 d G U P A 1
H23 H 0.7240 1.1962 0.1942 0.093 Uiso 0.519(18) 1 calc R U P A 1
C24 C 0.6931(8) 1.1176(14) 0.2556(6) 0.068(6) Uani 0.519(18) 1 d G U P A 1
H24 H 0.6432 1.0776 0.2451 0.082 Uiso 0.519(18) 1 calc R U P A 1
N1 N 0.5883(4) 0.3996(7) 0.3635(2) 0.0644(17) Uani 1 1 d . . . . .
N2 N 0.5854(4) 0.2835(6) 0.45860(19) 0.0540(15) Uani 1 1 d . . . . .
N3 N 0.5983(6) 1.0124(9) 0.3313(3) 0.086(2) Uani 1 1 d . . . . .
C25 C 0.8103(5) 0.4793(7) 0.4044(3) 0.0577(18) Uani 1 1 d . U . . .
O1 O 0.6662(5) 0.4843(7) 0.5084(2) 0.079(2) Uani 1 1 d . . . . .
O6 O 0.7575(3) 0.4061(5) 0.42009(18) 0.0602(13) Uani 1 1 d . U . . .
O3 O 0.6050(4) 0.6159(6) 0.4226(2) 0.0807(17) Uani 1 1 d . U . . .
O4 O 0.4703(5) 0.5647(6) 0.4330(2) 0.0836(18) Uani 1 1 d . U . . .
O5 O 0.7117(9) 0.9867(14) 0.3696(5) 0.091(4) Uani 0.5 1 d D U P . .
O7 O 0.7994(5) 0.5918(7) 0.3965(3) 0.098(2) Uani 1 1 d . U . . .
Zn1 Zn 0.63857(5) 0.44552(8) 0.43449(3) 0.0566(4) Uani 1 1 d . . . . .
O5B O 0.5345(8) 1.0551(14) 0.2683(5) 0.088(4) Uani 0.5 1 d D . P B -1
C18B C 0.6010(11) 1.0579(18) 0.2918(6) 0.065(5) Uani 0.481(18) 1 d . . P A 2
O1S O 0.7399(8) 0.6934(12) 0.5542(4) 0.169(4) Uani 1 1 d . U . . .
C19B C 0.6810(10) 1.1216(17) 0.2743(7) 0.067(6) Uani 0.481(18) 1 d DG U P A 2
C24B C 0.6909(10) 1.1329(18) 0.2266(6) 0.076(6) Uani 0.481(18) 1 d G U P A 2
H24B H 0.6497 1.0991 0.2064 0.091 Uiso 0.481(18) 1 calc R U P A 2
C23B C 0.7624(13) 1.195(2) 0.2090(5) 0.082(7) Uani 0.481(18) 1 d G U P A 2
H23B H 0.7690 1.2022 0.1771 0.099 Uiso 0.481(18) 1 calc R U P A 2
C22B C 0.8240(12) 1.245(3) 0.2391(7) 0.101(12) Uani 0.481(18) 1 d G U P A 2
H22B H 0.8719 1.2865 0.2274 0.121 Uiso 0.481(18) 1 calc R U P A 2
C21B C 0.8141(12) 1.234(3) 0.2868(7) 0.104(9) Uani 0.481(18) 1 d G U P A 2
H21B H 0.8554 1.2677 0.3070 0.125 Uiso 0.481(18) 1 calc R U P A 2
C20B C 0.7426(14) 1.1721(19) 0.3044(5) 0.083(7) Uani 0.481(18) 1 d G U P A 2
H20B H 0.7360 1.1646 0.3363 0.100 Uiso 0.481(18) 1 calc R U P A 2
H1B H 0.646(9) 0.452(13) 0.530(5) 0.125 Uiso 1 1 d . U . C 2
H1C H 0.679(10) 0.543(13) 0.508(6) 0.125 Uiso 1 1 d . U . D 2
H3N H 0.5764 1.0472 0.3062 0.125 Uiso 0.5 1 d . U P E 2
H3B H 0.6449 1.0283 0.3466 0.125 Uiso 0.5 1 d . U P F -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 N1 1.318(11) . ?
C1 C2 1.376(12) . ?
C1 H1 0.9300 . ?
C2 C3 1.352(12) . ?
C2 H2 0.9300 . ?
C3 C4 1.363(11) . ?
C3 C3 1.509(15) 2_655 ?
C4 C5 1.388(12) . ?
C4 H4 0.9300 . ?
C5 N1 1.308(11) . ?
C5 H5 0.9300 . ?
C6 C7 1.342(12) . ?
C6 N2 1.339(10) . ?
C6 H6 0.9300 . ?
C7 C8 1.381(9) . ?
C7 H7 0.9300 . ?
C8 C9 1.368(11) . ?
C8 C8 1.508(15) 5_656 ?
C9 C10 1.349(12) . ?
C9 H9 0.9300 . ?
C10 N2 1.346(9) . ?
C10 H10 0.9300 . ?
C11 O4 1.203(10) . ?
C11 O3 1.264(10) . ?
C11 C12 1.493(11) . ?
C12 C17 1.380(9) . ?
C12 C13 1.380(11) . ?
C13 C14 1.375(11) . ?
C13 H13 0.9300 . ?
C14 C15 1.376(11) . ?
C14 N3 1.426(11) . ?
C15 C16 1.389(11) . ?
C15 H15 0.9300 . ?
C16 C17 1.390(10) . ?
C16 C25 1.510(10) 3_455 ?
C17 H17 0.9300 . ?
C18 N3 1.190(16) . ?
C18 O5 1.214(14) . ?
C18 C19 1.469(14) . ?
C19 C20 1.3900 . ?
C19 C24 1.3900 . ?
C20 C21 1.3900 . ?
C20 H20 0.9300 . ?
C21 C22 1.3900 . ?
C21 H21 0.9300 . ?
C22 C23 1.3900 . ?
C22 H22 0.9300 . ?
C23 C24 1.3900 . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
N1 Zn1 2.234(6) . ?
N2 Zn1 2.051(7) . ?
N3 C18B 1.240(19) . ?
N3 H3N 0.878(9) . ?
N3 H3B 0.856(10) . ?
C25 O6 1.224(9) . ?
C25 O7 1.242(11) . ?
C25 C16 1.510(10) 3_545 ?
O1 Zn1 2.206(7) . ?
O1 H1B 0.79(13) . ?
O1 H1C 0.66(14) . ?
O6 Zn1 1.936(5) . ?
O3 Zn1 1.934(7) . ?
O5 H3B 1.298(14) . ?
C18B C19B 1.51(2) . ?
C18B H3N 0.578(17) . ?
C19B C24B 1.3900 . ?
C19B C20B 1.3900 . ?
C24B C23B 1.3900 . ?
C24B H24B 0.9300 . ?
C23B C22B 1.3900 . ?
C23B H23B 0.9300 . ?
C22B C21B 1.3900 . ?
C22B H22B 0.9300 . ?
C21B C20B 1.3900 . ?
C21B H21B 0.9300 . ?
C20B H20B 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
N1 C1 C2 123.0(9) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C3 C2 C1 120.1(8) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 117.6(7) . . ?
C2 C3 C3 121.6(9) . 2_655 ?
C4 C3 C3 120.8(9) . 2_655 ?
C3 C4 C5 118.7(8) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
N1 C5 C4 123.8(8) . . ?
N1 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
C7 C6 N2 123.8(7) . . ?
C7 C6 H6 118.1 . . ?
N2 C6 H6 118.1 . . ?
C6 C7 C8 120.2(7) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 116.5(7) . . ?
C9 C8 C8 122.5(7) . 5_656 ?
C7 C8 C8 121.0(8) . 5_656 ?
C10 C9 C8 120.6(7) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
N2 C10 C9 123.1(7) . . ?
N2 C10 H10 118.4 . . ?
C9 C10 H10 118.4 . . ?
O4 C11 O3 123.8(8) . . ?
O4 C11 C12 121.1(8) . . ?
O3 C11 C12 115.1(8) . . ?
C17 C12 C13 119.6(7) . . ?
C17 C12 C11 119.6(7) . . ?
C13 C12 C11 120.8(7) . . ?
C14 C13 C12 120.9(7) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C15 C14 C13 119.7(8) . . ?
C15 C14 N3 120.0(8) . . ?
C13 C14 N3 120.3(7) . . ?
C14 C15 C16 120.1(7) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C17 119.8(6) . . ?
C15 C16 C25 121.5(7) . 3_455 ?
C17 C16 C25 118.6(7) . 3_455 ?
C12 C17 C16 119.8(7) . . ?
C12 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
N3 C18 O5 119.4(14) . . ?
N3 C18 C19 119.1(13) . . ?
O5 C18 C19 121.5(15) . . ?
C20 C19 C24 120.0 . . ?
C20 C19 C18 115.6(13) . . ?
C24 C19 C18 124.4(13) . . ?
C19 C20 C21 120.0 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C22 120.0 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C23 C22 C21 120.0 . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C24 120.0 . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C24 C19 120.0 . . ?
C23 C24 H24 120.0 . . ?
C19 C24 H24 120.0 . . ?
C5 N1 C1 116.7(7) . . ?
C5 N1 Zn1 123.3(5) . . ?
C1 N1 Zn1 119.0(6) . . ?
C6 N2 C10 115.8(7) . . ?
C6 N2 Zn1 124.0(5) . . ?
C10 N2 Zn1 120.2(5) . . ?
C18 N3 C14 132.4(10) . . ?
C18B N3 C14 136.5(12) . . ?
C14 N3 H3N 114.2(9) . . ?
C14 N3 H3B 112.6(8) . . ?
O6 C25 O7 127.3(8) . . ?
O6 C25 C16 116.1(7) . 3_545 ?
O7 C25 C16 116.6(8) . 3_545 ?
Zn1 O1 H1B 128(10) . . ?
Zn1 O1 H1C 102(10) . . ?
H1B O1 H1C 124(10) . . ?
C25 O6 Zn1 125.2(5) . . ?
C11 O3 Zn1 116.0(6) . . ?
O3 Zn1 O6 115.0(3) . . ?
O3 Zn1 N2 139.3(2) . . ?
O6 Zn1 N2 105.7(2) . . ?
O3 Zn1 O1 92.2(3) . . ?
O6 Zn1 O1 94.4(2) . . ?
N2 Zn1 O1 84.7(3) . . ?
O3 Zn1 N1 87.7(3) . . ?
O6 Zn1 N1 94.3(2) . . ?
N2 Zn1 N1 89.2(3) . . ?
O1 Zn1 N1 170.5(3) . . ?
N3 C18B C19B 121.6(16) . . ?
C19B C18B H3N 152(2) . . ?
C24B C19B C20B 120.0 . . ?
C24B C19B C18B 118.1(15) . . ?
C20B C19B C18B 121.8(15) . . ?
C23B C24B C19B 120.0 . . ?
C23B C24B H24B 120.0 . . ?
C19B C24B H24B 120.0 . . ?
C24B C23B C22B 120.0 . . ?
C24B C23B H23B 120.0 . . ?
C22B C23B H23B 120.0 . . ?
C23B C22B C21B 120.0 . . ?
C23B C22B H22B 120.0 . . ?
C21B C22B H22B 120.0 . . ?
C20B C21B C22B 120.0 . . ?
C20B C21B H21B 120.0 . . ?
C22B C21B H21B 120.0 . . ?
C21B C20B C19B 120.0 . . ?
C21B C20B H20B 120.0 . . ?
C19B C20B H20B 120.0 . . ?

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 C3 1.6(17) . . . . ?
C1 C2 C3 C4 -2.6(15) . . . . ?
C1 C2 C3 C3 177.7(8) . . . 2_655 ?
C2 C3 C4 C5 1.0(15) . . . . ?
C3 C3 C4 C5 -179.3(8) 2_655 . . . ?
C3 C4 C5 N1 1.8(18) . . . . ?
N2 C6 C7 C8 -1.5(13) . . . . ?
C6 C7 C8 C9 1.0(11) . . . . ?
C6 C7 C8 C8 179.1(8) . . . 5_656 ?
C7 C8 C9 C10 -0.2(12) . . . . ?
C8 C8 C9 C10 -178.3(8) 5_656 . . . ?
C8 C9 C10 N2 -0.2(13) . . . . ?
O4 C11 C12 C17 18.0(12) . . . . ?
O3 C11 C12 C17 -161.8(8) . . . . ?
O4 C11 C12 C13 -163.1(8) . . . . ?
O3 C11 C12 C13 17.1(11) . . . . ?
C17 C12 C13 C14 1.7(12) . . . . ?
C11 C12 C13 C14 -177.2(7) . . . . ?
C12 C13 C14 C15 1.9(12) . . . . ?
C12 C13 C14 N3 -179.4(8) . . . . ?
C13 C14 C15 C16 -3.2(12) . . . . ?
N3 C14 C15 C16 178.2(8) . . . . ?
C14 C15 C16 C17 0.7(11) . . . . ?
C14 C15 C16 C25 178.0(7) . . . 3_455 ?
C13 C12 C17 C16 -4.2(11) . . . . ?
C11 C12 C17 C16 174.7(7) . . . . ?
C15 C16 C17 C12 3.0(11) . . . . ?
C25 C16 C17 C12 -174.4(7) 3_455 . . . ?
N3 C18 C19 C20 155.7(14) . . . . ?
O5 C18 C19 C20 -27(2) . . . . ?
N3 C18 C19 C24 -25(2) . . . . ?
O5 C18 C19 C24 152.1(16) . . . . ?
C24 C19 C20 C21 0.0 . . . . ?
C18 C19 C20 C21 179.1(15) . . . . ?
C19 C20 C21 C22 0.0 . . . . ?
C20 C21 C22 C23 0.0 . . . . ?
C21 C22 C23 C24 0.0 . . . . ?
C22 C23 C24 C19 0.0 . . . . ?
C20 C19 C24 C23 0.0 . . . . ?
C18 C19 C24 C23 -179.0(17) . . . . ?
C4 C5 N1 C1 -2.8(16) . . . . ?
C4 C5 N1 Zn1 165.4(9) . . . . ?
C2 C1 N1 C5 1.1(16) . . . . ?
C2 C1 N1 Zn1 -167.6(8) . . . . ?
C7 C6 N2 C10 1.2(12) . . . . ?
C7 C6 N2 Zn1 -179.4(6) . . . . ?
C9 C10 N2 C6 -0.3(12) . . . . ?
C9 C10 N2 Zn1 -179.7(6) . . . . ?
O5 C18 N3 C14 1(3) . . . . ?
C19 C18 N3 C14 178.7(11) . . . . ?
C15 C14 N3 C18 133.9(15) . . . . ?
C13 C14 N3 C18 -44.7(18) . . . . ?
C15 C14 N3 C18B -60.3(19) . . . . ?
C13 C14 N3 C18B 121.1(17) . . . . ?
O7 C25 O6 Zn1 3.1(12) . . . . ?
C16 C25 O6 Zn1 -175.0(4) 3_545 . . . ?
O4 C11 O3 Zn1 14.3(11) . . . . ?
C12 C11 O3 Zn1 -165.9(5) . . . . ?
C14 N3 C18B C19B -176.9(13) . . . . ?
N3 C18B C19B C24B 158.8(15) . . . . ?
N3 C18B C19B C20B -23(2) . . . . ?
C20B C19B C24B C23B 0.0 . . . . ?
C18B C19B C24B C23B 178(2) . . . . ?
C19B C24B C23B C22B 0.0 . . . . ?
C24B C23B C22B C21B 0.0 . . . . ?
C23B C22B C21B C20B 0.0 . . . . ?
C22B C21B C20B C19B 0.0 . . . . ?
C24B C19B C20B C21B 0.0 . . . . ?
C18B C19B C20B C21B -178(2) . . . . ?

_refine_diff_density_max         1.975
_refine_diff_density_min         -0.794
_refine_diff_density_rms         0.130

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

data_5
_database_code_depnum_ccdc_archive 'CCDC 1490732'
_audit_update_record             
;
2016-07-05 deposited with the CCDC.
2016-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H23 Cd N5 O7'
_chemical_formula_weight         641.90

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'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   13.0001(6)
_cell_length_b                   10.0706(5)
_cell_length_c                   20.0881(10)
_cell_angle_alpha                90
_cell_angle_beta                 105.006(2)
_cell_angle_gamma                90
_cell_volume                     2540.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9927
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      26.35

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.918
_shelx_estimated_absorpt_T_min   0.739
_shelx_estimated_absorpt_T_max   0.852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7
_exptl_absorpt_correction_T_max  0.8
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            51716
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.279
_diffrn_reflns_theta_max         26.423
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5210
_reflns_number_gt                4528
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1999)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury CSD 3.5.1, 2008'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0431P)²+1.7917P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5210
_refine_ls_number_parameters     376
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0835
_refine_ls_wR_factor_gt          0.0794
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_restrained_S_all      1.123
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.46381(17) 0.7016(2) -0.11558(11) 0.0428(5) Uani 1 1 d . . . . .
Cd1 Cd 0.52851(2) 0.55710(2) 0.09085(2) 0.02819(8) Uani 1 1 d . . . . .
N2 N 0.70761(19) 0.5415(2) 0.13179(12) 0.0324(5) Uani 1 1 d . . . . .
N3 N 1.2647(2) 0.4663(4) 0.26172(19) 0.0640(9) Uani 1 1 d . . . . .
O1 O 0.56750(17) 0.60349(18) -0.02504(10) 0.0366(5) Uani 1 1 d . . . . .
O5 O 0.38052(17) 0.69525(18) 0.04739(12) 0.0447(5) Uani 1 1 d . . . . .
O6 O 0.52925(16) 0.79101(19) 0.10443(11) 0.0389(5) Uani 1 1 d . . . . .
N1 N 0.8739(2) 0.9216(2) 0.04623(14) 0.0383(6) Uani 1 1 d . . . . .
O7 O 0.92569(18) 1.1353(2) 0.06916(13) 0.0509(6) Uani 1 1 d . . . . .
C4 C 0.6138(2) 1.0692(2) -0.04739(14) 0.0278(5) Uani 1 1 d . . . . .
O3 O 0.4900(2) 0.5363(2) 0.19705(12) 0.0522(6) Uani 1 1 d . . . . .
O8 O 0.9034(2) 0.6240(3) 1.00760(17) 0.0699(8) Uani 1 1 d . . . . .
C21 C 0.7575(3) 0.4279(3) 0.12546(18) 0.0420(7) Uani 1 1 d . . . . .
H21 H 0.7173 0.3562 0.1039 0.050 Uiso 1 1 calc R U . . .
C20 C 0.8662(3) 0.4127(3) 0.14962(18) 0.0427(7) Uani 1 1 d . . . . .
H20 H 0.8981 0.3325 0.1436 0.051 Uiso 1 1 calc R U . . .
C19 C 0.9273(2) 0.5166(3) 0.18271(15) 0.0354(6) Uani 1 1 d . . . . .
C18 C 0.8754(2) 0.6345(3) 0.18928(16) 0.0413(7) Uani 1 1 d . . . . .
H18 H 0.9136 0.7069 0.2117 0.050 Uiso 1 1 calc R U . . .
C17 C 0.7672(2) 0.6432(3) 0.16247(16) 0.0390(7) Uani 1 1 d . . . . .
H17 H 0.7339 0.7237 0.1658 0.047 Uiso 1 1 calc R U . . .
C22 C 1.0447(2) 0.5013(3) 0.20976(16) 0.0388(7) Uani 1 1 d . . . . .
C26 C 1.0987(3) 0.5550(4) 0.27227(18) 0.0521(9) Uani 1 1 d . . . . .
H26 H 1.0626 0.6048 0.2980 0.062 Uiso 1 1 calc R U . . .
C25 C 1.2071(3) 0.5337(5) 0.2960(2) 0.0646(11) Uani 1 1 d . . . . .
H25 H 1.2419 0.5689 0.3387 0.077 Uiso 1 1 calc R U . . .
C24 C 1.2121(3) 0.4171(4) 0.2013(2) 0.0583(10) Uani 1 1 d . . . . .
H24 H 1.2509 0.3707 0.1760 0.070 Uiso 1 1 calc R U . . .
C23 C 1.1039(3) 0.4296(3) 0.1733(2) 0.0488(8) Uani 1 1 d . . . . .
H23 H 1.0712 0.3911 0.1311 0.059 Uiso 1 1 calc R U . . .
C16 C 0.4347(2) 0.7975(2) 0.06795(14) 0.0299(6) Uani 1 1 d . . . . .
C1 C 0.5372(2) 0.7062(3) -0.06310(14) 0.0307(6) Uani 1 1 d . . . . .
C15 C 0.4867(3) 0.6168(4) 0.24312(17) 0.0516(9) Uani 1 1 d . . . . .
H15 H 0.4593 0.5858 0.2786 0.062 Uiso 1 1 calc R U . . .
N4 N 0.5172(3) 0.7396(4) 0.24701(17) 0.0572(9) Uani 1 1 d . . . . .
C2 C 0.5992(2) 0.8327(2) -0.04368(13) 0.0289(5) Uani 1 1 d . . . . .
C7 C 0.7033(2) 0.8261(2) -0.00432(14) 0.0328(6) Uani 1 1 d . . . . .
H7 H 0.7321 0.7443 0.0122 0.039 Uiso 1 1 calc R U . . .
C6 C 0.7659(2) 0.9399(2) 0.01109(15) 0.0322(6) Uani 1 1 d . . . . .
C8 C 0.9471(2) 1.0164(3) 0.07269(15) 0.0349(6) Uani 1 1 d . . . . .
C9 C 1.0560(2) 0.9702(3) 0.11018(16) 0.0367(6) Uani 1 1 d . . . . .
C10 C 1.0823(3) 0.8386(3) 0.1271(2) 0.0524(9) Uani 1 1 d . . . . .
H10 H 1.0316 0.7723 0.1127 0.063 Uiso 1 1 calc R U . . .
C11 C 1.1832(3) 0.8064(4) 0.1652(2) 0.0643(11) Uani 1 1 d . . . . .
H11 H 1.2007 0.7181 0.1761 0.077 Uiso 1 1 calc R U . . .
C12 C 1.2585(3) 0.9040(4) 0.1872(2) 0.0598(10) Uani 1 1 d . . . . .
H12 H 1.3257 0.8819 0.2144 0.072 Uiso 1 1 calc R U . . .
C13 C 1.2342(3) 1.0330(4) 0.1691(2) 0.0619(11) Uani 1 1 d . . . . .
H13 H 1.2856 1.0987 0.1830 0.074 Uiso 1 1 calc R U . . .
C14 C 1.1334(3) 1.0663(3) 0.1299(2) 0.0516(9) Uani 1 1 d . . . . .
H14 H 1.1177 1.1541 0.1169 0.062 Uiso 1 1 calc R U . . .
C5 C 0.7194(2) 1.0621(2) -0.00956(15) 0.0321(6) Uani 1 1 d . . . . .
H5 H 0.7591 1.1395 0.0020 0.039 Uiso 1 1 calc R U . . .
C3 C 0.5542(2) 0.9552(2) -0.06577(14) 0.0282(5) Uani 1 1 d . . . . .
H3 H 0.4844 0.9604 -0.0927 0.034 Uiso 1 1 calc R U . . .
N5 N 0.8600(4) 0.4122(4) 0.9778(2) 0.0728(10) Uani 1 1 d D . . . .
C27 C 0.8384(4) 0.5299(4) 0.9886(2) 0.0674(11) Uani 1 1 d . . . . .
H27 H 0.7666 0.5503 0.9818 0.081 Uiso 1 1 calc R U . . .
H4A H 0.922(2) 0.364(4) 0.976(3) 0.101 Uiso 1 1 d D U . . .
H4B H 0.801(2) 0.360(4) 0.969(3) 0.101 Uiso 1 1 d D U . . .
H5A H 0.537(4) 0.770(5) 0.212(3) 0.101 Uiso 1 1 d . U . . .
H5B H 0.507(4) 0.778(5) 0.279(3) 0.101 Uiso 1 1 d . U . . .
H1N H 0.898(4) 0.840(5) 0.047(3) 0.101 Uiso 1 1 d . U . . .


_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
O2 C1 1.226(4) . ?
O2 Cd1 2.649(2) 3_665 ?
Cd1 O1 2.2509(19) 3_665 ?
Cd1 N2 2.265(2) . ?
Cd1 O3 2.324(2) . ?
Cd1 O5 2.352(2) . ?
Cd1 O6 2.3711(19) . ?
Cd1 O1 2.551(2) . ?
Cd1 O2 2.649(2) 3_665 ?
Cd1 C16 2.696(3) . ?
N2 C17 1.335(4) . ?
N2 C21 1.337(4) . ?
N3 C24 1.325(5) . ?
N3 C25 1.328(6) . ?
O1 C1 1.286(3) . ?
O1 Cd1 2.2509(19) 3_665 ?
O5 C16 1.255(3) . ?
O6 C16 1.259(3) . ?
N1 C8 1.356(4) . ?
N1 C6 1.411(4) . ?
N1 H1N 0.88(5) . ?
O7 C8 1.227(4) . ?
C4 C3 1.382(4) . ?
C4 C5 1.388(4) . ?
C4 C16 1.495(3) 3_675 ?
O3 C15 1.240(4) . ?
O8 C27 1.261(5) . ?
C21 C20 1.378(4) . ?
C21 H21 0.9300 . ?
C20 C19 1.377(4) . ?
C20 H20 0.9300 . ?
C19 C18 1.389(4) . ?
C19 C22 1.489(4) . ?
C18 C17 1.372(4) . ?
C18 H18 0.9300 . ?
C17 H17 0.9300 . ?
C22 C26 1.380(5) . ?
C22 C23 1.393(5) . ?
C26 C25 1.383(5) . ?
C26 H26 0.9300 . ?
C25 H25 0.9300 . ?
C24 C23 1.378(5) . ?
C24 H24 0.9300 . ?
C23 H23 0.9300 . ?
C16 C4 1.495(3) 3_675 ?
C1 C2 1.504(4) . ?
C15 N4 1.295(6) . ?
C15 H15 0.9300 . ?
N4 H5A 0.87(5) . ?
N4 H5B 0.78(5) . ?
C2 C7 1.380(4) . ?
C2 C3 1.388(4) . ?
C7 C6 1.393(4) . ?
C7 H7 0.9300 . ?
C6 C5 1.387(4) . ?
C8 C9 1.495(4) . ?
C9 C14 1.377(5) . ?
C9 C10 1.388(4) . ?
C10 C11 1.375(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.364(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C5 H5 0.9300 . ?
C3 H3 0.9300 . ?
N5 C27 1.249(5) . ?
N5 H4A 0.952(19) . ?
N5 H4B 0.907(19) . ?
C27 H27 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
C1 O2 Cd1 83.89(16) . 3_665 ?
O1 Cd1 N2 121.66(8) 3_665 . ?
O1 Cd1 O3 104.82(8) 3_665 . ?
N2 Cd1 O3 96.09(9) . . ?
O1 Cd1 O5 86.05(7) 3_665 . ?
N2 Cd1 O5 147.27(8) . . ?
O3 Cd1 O5 92.52(9) . . ?
O1 Cd1 O6 140.04(7) 3_665 . ?
N2 Cd1 O6 93.10(7) . . ?
O3 Cd1 O6 88.81(8) . . ?
O5 Cd1 O6 55.49(7) . . ?
O1 Cd1 O1 78.85(7) 3_665 . ?
N2 Cd1 O1 85.16(8) . . ?
O3 Cd1 O1 174.56(7) . . ?
O5 Cd1 O1 83.66(7) . . ?
O6 Cd1 O1 85.83(7) . . ?
O1 Cd1 O2 52.54(7) 3_665 3_665 ?
N2 Cd1 O2 83.01(7) . 3_665 ?
O3 Cd1 O2 75.27(8) . 3_665 ?
O5 Cd1 O2 129.71(7) . 3_665 ?
O6 Cd1 O2 163.05(7) . 3_665 ?
O1 Cd1 O2 110.16(6) . 3_665 ?
O1 Cd1 C16 112.79(8) 3_665 . ?
N2 Cd1 C16 120.09(8) . . ?
O3 Cd1 C16 92.41(8) . . ?
O5 Cd1 C16 27.74(8) . . ?
O6 Cd1 C16 27.84(8) . . ?
O1 Cd1 C16 82.41(7) . . ?
O2 Cd1 C16 155.28(8) 3_665 . ?
C17 N2 C21 117.5(3) . . ?
C17 N2 Cd1 122.24(19) . . ?
C21 N2 Cd1 120.23(19) . . ?
C24 N3 C25 116.1(3) . . ?
C1 O1 Cd1 101.01(17) . 3_665 ?
C1 O1 Cd1 125.96(17) . . ?
Cd1 O1 Cd1 101.15(7) 3_665 . ?
C16 O5 Cd1 91.59(17) . . ?
C16 O6 Cd1 90.59(15) . . ?
C8 N1 C6 127.6(2) . . ?
C8 N1 H1N 116(3) . . ?
C6 N1 H1N 116(3) . . ?
C3 C4 C5 120.7(2) . . ?
C3 C4 C16 120.3(2) . 3_675 ?
C5 C4 C16 119.0(2) . 3_675 ?
C15 O3 Cd1 133.2(3) . . ?
N2 C21 C20 122.7(3) . . ?
N2 C21 H21 118.7 . . ?
C20 C21 H21 118.7 . . ?
C19 C20 C21 119.8(3) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C19 C18 117.5(3) . . ?
C20 C19 C22 120.4(3) . . ?
C18 C19 C22 122.1(3) . . ?
C17 C18 C19 119.5(3) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
N2 C17 C18 123.0(3) . . ?
N2 C17 H17 118.5 . . ?
C18 C17 H17 118.5 . . ?
C26 C22 C23 117.5(3) . . ?
C26 C22 C19 121.5(3) . . ?
C23 C22 C19 121.0(3) . . ?
C22 C26 C25 119.1(4) . . ?
C22 C26 H26 120.5 . . ?
C25 C26 H26 120.5 . . ?
N3 C25 C26 124.1(4) . . ?
N3 C25 H25 117.9 . . ?
C26 C25 H25 117.9 . . ?
N3 C24 C23 124.8(4) . . ?
N3 C24 H24 117.6 . . ?
C23 C24 H24 117.6 . . ?
C24 C23 C22 118.5(3) . . ?
C24 C23 H23 120.8 . . ?
C22 C23 H23 120.8 . . ?
O5 C16 O6 121.9(2) . . ?
O5 C16 C4 119.0(2) . 3_675 ?
O6 C16 C4 119.1(2) . 3_675 ?
O5 C16 Cd1 60.67(14) . . ?
O6 C16 Cd1 61.57(13) . . ?
C4 C16 Cd1 173.27(19) 3_675 . ?
O2 C1 O1 122.0(2) . . ?
O2 C1 C2 120.1(2) . . ?
O1 C1 C2 117.8(2) . . ?
O3 C15 N4 126.9(4) . . ?
O3 C15 H15 116.6 . . ?
N4 C15 H15 116.6 . . ?
C15 N4 H5A 116(4) . . ?
C15 N4 H5B 114(4) . . ?
H5A N4 H5B 129(5) . . ?
C7 C2 C3 119.7(2) . . ?
C7 C2 C1 119.2(2) . . ?
C3 C2 C1 121.1(2) . . ?
C2 C7 C6 121.2(2) . . ?
C2 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C5 C6 C7 118.6(3) . . ?
C5 C6 N1 124.5(2) . . ?
C7 C6 N1 116.9(2) . . ?
O7 C8 N1 122.6(3) . . ?
O7 C8 C9 120.3(3) . . ?
N1 C8 C9 117.1(3) . . ?
C14 C9 C10 119.0(3) . . ?
C14 C9 C8 116.9(3) . . ?
C10 C9 C8 124.1(3) . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.5(4) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 119.9(3) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.1(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 120.0 . . ?
C9 C14 C13 120.5(3) . . ?
C9 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C4 C3 C2 119.5(3) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C27 N5 H4A 136(3) . . ?
C27 N5 H4B 112(3) . . ?
H4A N5 H4B 112(4) . . ?
N5 C27 O8 127.0(5) . . ?
N5 C27 H27 116.5 . . ?
O8 C27 H27 116.5 . . ?

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
C17 N2 C21 C20 0.5(5) . . . . ?
Cd1 N2 C21 C20 -179.8(3) . . . . ?
N2 C21 C20 C19 1.0(5) . . . . ?
C21 C20 C19 C18 -0.9(5) . . . . ?
C21 C20 C19 C22 179.4(3) . . . . ?
C20 C19 C18 C17 -0.6(5) . . . . ?
C22 C19 C18 C17 179.1(3) . . . . ?
C21 N2 C17 C18 -2.2(5) . . . . ?
Cd1 N2 C17 C18 178.1(2) . . . . ?
C19 C18 C17 N2 2.3(5) . . . . ?
C20 C19 C22 C26 -140.4(3) . . . . ?
C18 C19 C22 C26 39.9(4) . . . . ?
C20 C19 C22 C23 38.3(4) . . . . ?
C18 C19 C22 C23 -141.4(3) . . . . ?
C23 C22 C26 C25 -1.0(5) . . . . ?
C19 C22 C26 C25 177.7(3) . . . . ?
C24 N3 C25 C26 -0.5(6) . . . . ?
C22 C26 C25 N3 1.5(6) . . . . ?
C25 N3 C24 C23 -1.0(6) . . . . ?
N3 C24 C23 C22 1.4(6) . . . . ?
C26 C22 C23 C24 -0.3(5) . . . . ?
C19 C22 C23 C24 -179.0(3) . . . . ?
Cd1 O5 C16 O6 -6.5(3) . . . . ?
Cd1 O5 C16 C4 172.3(2) . . . 3_675 ?
Cd1 O6 C16 O5 6.5(3) . . . . ?
Cd1 O6 C16 C4 -172.4(2) . . . 3_675 ?
Cd1 O2 C1 O1 -6.8(3) 3_665 . . . ?
Cd1 O2 C1 C2 169.5(2) 3_665 . . . ?
Cd1 O1 C1 O2 8.1(3) 3_665 . . . ?
Cd1 O1 C1 O2 -104.5(3) . . . . ?
Cd1 O1 C1 C2 -168.27(19) 3_665 . . . ?
Cd1 O1 C1 C2 79.1(3) . . . . ?
Cd1 O3 C15 N4 -8.6(6) . . . . ?
O2 C1 C2 C7 -153.4(3) . . . . ?
O1 C1 C2 C7 23.1(4) . . . . ?
O2 C1 C2 C3 25.4(4) . . . . ?
O1 C1 C2 C3 -158.1(3) . . . . ?
C3 C2 C7 C6 -3.0(4) . . . . ?
C1 C2 C7 C6 175.8(3) . . . . ?
C2 C7 C6 C5 4.7(4) . . . . ?
C2 C7 C6 N1 -174.4(3) . . . . ?
C8 N1 C6 C5 8.2(5) . . . . ?
C8 N1 C6 C7 -172.8(3) . . . . ?
C6 N1 C8 O7 0.6(5) . . . . ?
C6 N1 C8 C9 177.7(3) . . . . ?
O7 C8 C9 C14 -10.2(4) . . . . ?
N1 C8 C9 C14 172.7(3) . . . . ?
O7 C8 C9 C10 168.3(3) . . . . ?
N1 C8 C9 C10 -8.8(5) . . . . ?
C14 C9 C10 C11 2.3(5) . . . . ?
C8 C9 C10 C11 -176.3(3) . . . . ?
C9 C10 C11 C12 0.5(6) . . . . ?
C10 C11 C12 C13 -2.5(6) . . . . ?
C11 C12 C13 C14 1.6(6) . . . . ?
C10 C9 C14 C13 -3.2(6) . . . . ?
C8 C9 C14 C13 175.5(3) . . . . ?
C12 C13 C14 C9 1.3(6) . . . . ?
C7 C6 C5 C4 -2.8(4) . . . . ?
N1 C6 C5 C4 176.3(3) . . . . ?
C3 C4 C5 C6 -0.9(4) . . . . ?
C16 C4 C5 C6 179.0(3) 3_675 . . . ?
C5 C4 C3 C2 2.7(4) . . . . ?
C16 C4 C3 C2 -177.2(2) 3_675 . . . ?
C7 C2 C3 C4 -0.7(4) . . . . ?
C1 C2 C3 C4 -179.5(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C21 H21 O2 0.93 2.49 3.118(4) 124.6 3_665
C20 H20 O7 0.93 2.57 3.415(4) 151.9 1_545
C7 H7 O8 0.93 2.56 3.262(4) 132.9 1_554
C5 H5 O7 0.93 2.24 2.835(4) 121.5 .
N5 H4A O8 0.952(19) 2.21(3) 3.036(5) 145(4) 3_767
N5 H4B O5 0.907(19) 2.36(2) 3.222(5) 158(4) 3_666
N4 H5A O6 0.87(5) 2.14(5) 2.954(4) 155(5) .
N4 H5B O2 0.78(5) 2.34(5) 3.073(4) 155(5) 4_576
N1 H1N O8 0.88(5) 2.32(5) 3.144(3) 155(4) 1_554

_refine_diff_density_max         0.877
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.105

_shelxl_version_number           2014/6

