# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015

####################################################################### 
# 
# 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 1422595'
_audit_update_record             
;
2015-11-16 deposited with the CCDC.
2015-11-30 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            'C12 H10 N4 O9 Zn'
_chemical_formula_weight         419.61

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                   7.7271(7)
_cell_length_b                   9.6737(8)
_cell_length_c                   10.9425(10)
_cell_angle_alpha                69.740(3)
_cell_angle_beta                 87.236(2)
_cell_angle_gamma                67.112(3)
_cell_volume                     703.38(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2982
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      25.32

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.981
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.813
_shelx_estimated_absorpt_T_min   0.569
_shelx_estimated_absorpt_T_max   0.713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5
_exptl_absorpt_correction_T_max  0.6
_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 PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6693
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.445
_diffrn_reflns_theta_max         25.344
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             2528
_reflns_number_gt                2148
_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)+(0.0639P)²] 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         2528
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1013
_refine_ls_wR_factor_gt          0.0972
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_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
O4 O 1.1769(4) -0.3567(3) 0.4170(3) 0.0387(6) Uani 1 1 d . . . . .
O3 O 1.3894(3) -0.2981(3) 0.4940(3) 0.0393(6) Uani 1 1 d . . . . .
C5 C 1.2365(4) -0.2603(4) 0.4354(3) 0.0222(7) Uani 1 1 d . . . . .
C4 C 1.1094(4) -0.0865(3) 0.3774(3) 0.0178(6) Uani 1 1 d . . . . .
C6 C 0.9326(4) -0.0394(4) 0.3145(3) 0.0206(6) Uani 1 1 d . . . . .
H6 H 0.8894 -0.1159 0.3122 0.025 Uiso 1 1 calc R U . . .
Zn1 Zn 1.34266(5) 0.42052(4) 0.43990(4) 0.02769(16) Uani 1 1 d . . . . .
O8 O 1.4195(4) 0.5180(3) 0.2400(2) 0.0398(6) Uani 1 1 d . . . . .
H8A H 1.4581 0.6028 0.2348 0.060 Uiso 1 1 d R U . . .
H8B H 1.3120 0.5595 0.1777 0.060 Uiso 1 1 d R U . . .
O1 O 1.2815(4) 0.2639(3) 0.3943(3) 0.0431(7) Uani 1 1 d . . . . .
O2 O 1.0300(3) 0.4602(3) 0.2677(2) 0.0368(6) Uani 1 1 d . . . . .
O5 O 0.3381(4) 0.3977(3) 0.0236(3) 0.0427(7) Uani 1 1 d . . . . .
N4 N 0.1934(4) 0.0326(3) 0.0557(2) 0.0243(6) Uani 1 1 d . . . . .
H4N H 0.1568 -0.0426 0.0615 0.029 Uiso 1 1 calc R U . . .
O7 O 0.4601(3) -0.1559(3) 0.1768(2) 0.0313(5) Uani 1 1 d . . . . .
O6 O -0.0775(3) 0.2159(3) -0.0721(2) 0.0344(6) Uani 1 1 d . . . . .
O9 O 1.2579(4) 0.3455(4) 0.6278(3) 0.0586(8) Uani 1 1 d . . . . .
H9A H 1.1411 0.4274 0.6340 0.088 Uiso 1 1 d R U . . .
H9B H 1.3531 0.3277 0.6914 0.088 Uiso 1 1 d R U . . .
C3 C 1.1726(4) 0.0285(4) 0.3822(3) 0.0188(6) Uani 1 1 d . . . . .
H3 H 1.2897 -0.0036 0.4260 0.023 Uiso 1 1 calc R U . . .
N1 N 0.6429(4) 0.1759(3) 0.1876(3) 0.0242(6) Uani 1 1 d . . . . .
H1N H 0.5764 0.2769 0.1500 0.029 Uiso 1 1 calc R U . . .
N2 N 0.5799(3) 0.0728(3) 0.1825(2) 0.0226(6) Uani 1 1 d . . . . .
C7 C 0.8214(4) 0.1234(4) 0.2550(3) 0.0215(6) Uani 1 1 d . . . . .
C1 C 1.1281(4) 0.3154(4) 0.3267(3) 0.0230(7) Uani 1 1 d . . . . .
C2 C 1.0602(4) 0.1919(4) 0.3211(3) 0.0187(6) Uani 1 1 d . . . . .
C8 C 0.8843(4) 0.2384(4) 0.2572(3) 0.0217(6) Uani 1 1 d . . . . .
H8 H 0.8090 0.3468 0.2159 0.026 Uiso 1 1 calc R U . . .
C9 C 0.4177(4) 0.1181(4) 0.1163(3) 0.0210(6) Uani 1 1 d . . . . .
C10 C 0.2982(4) 0.2831(4) 0.0359(3) 0.0259(7) Uani 1 1 d . . . . .
N3 N 0.1355(4) 0.3040(3) -0.0273(3) 0.0286(6) Uani 1 1 d . . . . .
H3N H 0.0661 0.4000 -0.0776 0.034 Uiso 1 1 calc R U . . .
C11 C 0.0738(4) 0.1866(4) -0.0178(3) 0.0255(7) Uani 1 1 d . . . . .
C12 C 0.3647(4) -0.0129(4) 0.1204(3) 0.0222(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 C5 1.263(4) . ?
O4 Zn1 1.964(2) 1_545 ?
O3 C5 1.231(4) . ?
O3 Zn1 1.964(2) 2_856 ?
C5 C4 1.494(4) . ?
C4 C6 1.393(4) . ?
C4 C3 1.393(4) . ?
C6 C7 1.390(4) . ?
C6 H6 0.9300 . ?
Zn1 O4 1.964(2) 1_565 ?
Zn1 O3 1.964(2) 2_856 ?
Zn1 O1 1.968(2) . ?
Zn1 O9 2.095(3) . ?
Zn1 O8 2.215(3) . ?
O8 H8A 0.9600 . ?
O8 H8B 0.9600 . ?
O1 C1 1.253(4) . ?
O2 C1 1.244(4) . ?
O5 C10 1.226(4) . ?
N4 C12 1.367(4) . ?
N4 C11 1.375(4) . ?
N4 H4N 0.8600 . ?
O7 C12 1.223(4) . ?
O6 C11 1.222(4) . ?
O9 H9A 0.9600 . ?
O9 H9B 0.9600 . ?
C3 C2 1.399(4) . ?
C3 H3 0.9300 . ?
N1 N2 1.285(3) . ?
N1 C7 1.414(4) . ?
N1 H1N 0.8600 . ?
N2 C9 1.315(4) . ?
C7 C8 1.384(4) . ?
C1 C2 1.499(4) . ?
C2 C8 1.392(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.461(4) . ?
C9 C12 1.463(4) . ?
C10 N3 1.374(4) . ?
N3 C11 1.365(4) . ?
N3 H3N 0.8600 . ?

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
C5 O4 Zn1 122.7(2) . 1_545 ?
C5 O3 Zn1 158.8(2) . 2_856 ?
O3 C5 O4 125.5(3) . . ?
O3 C5 C4 118.6(3) . . ?
O4 C5 C4 115.9(3) . . ?
C6 C4 C3 120.3(3) . . ?
C6 C4 C5 120.3(3) . . ?
C3 C4 C5 119.4(3) . . ?
C7 C6 C4 119.1(3) . . ?
C7 C6 H6 120.4 . . ?
C4 C6 H6 120.4 . . ?
O4 Zn1 O3 130.17(10) 1_565 2_856 ?
O4 Zn1 O1 128.01(10) 1_565 . ?
O3 Zn1 O1 101.77(10) 2_856 . ?
O4 Zn1 O9 89.29(12) 1_565 . ?
O3 Zn1 O9 91.89(11) 2_856 . ?
O1 Zn1 O9 91.15(13) . . ?
O4 Zn1 O8 86.55(10) 1_565 . ?
O3 Zn1 O8 90.61(10) 2_856 . ?
O1 Zn1 O8 91.59(11) . . ?
O9 Zn1 O8 175.84(10) . . ?
Zn1 O8 H8A 109.3 . . ?
Zn1 O8 H8B 109.4 . . ?
H8A O8 H8B 109.5 . . ?
C1 O1 Zn1 117.2(2) . . ?
C12 N4 C11 126.5(3) . . ?
C12 N4 H4N 116.7 . . ?
C11 N4 H4N 116.7 . . ?
Zn1 O9 H9A 109.3 . . ?
Zn1 O9 H9B 109.2 . . ?
H9A O9 H9B 109.5 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
N2 N1 C7 120.1(3) . . ?
N2 N1 H1N 120.0 . . ?
C7 N1 H1N 120.0 . . ?
N1 N2 C9 121.3(3) . . ?
C8 C7 C6 121.0(3) . . ?
C8 C7 N1 118.1(3) . . ?
C6 C7 N1 120.8(3) . . ?
O2 C1 O1 124.2(3) . . ?
O2 C1 C2 119.3(3) . . ?
O1 C1 C2 116.5(3) . . ?
C8 C2 C3 119.4(3) . . ?
C8 C2 C1 120.5(3) . . ?
C3 C2 C1 120.0(3) . . ?
C7 C8 C2 120.0(3) . . ?
C7 C8 H8 120.0 . . ?
C2 C8 H8 120.0 . . ?
N2 C9 C10 125.3(3) . . ?
N2 C9 C12 114.9(3) . . ?
C10 C9 C12 119.6(3) . . ?
O5 C10 N3 120.9(3) . . ?
O5 C10 C9 123.1(3) . . ?
N3 C10 C9 116.0(3) . . ?
C11 N3 C10 126.0(3) . . ?
C11 N3 H3N 117.0 . . ?
C10 N3 H3N 117.0 . . ?
O6 C11 N3 122.2(3) . . ?
O6 C11 N4 121.9(3) . . ?
N3 C11 N4 115.9(3) . . ?
O7 C12 N4 119.1(3) . . ?
O7 C12 C9 125.2(3) . . ?
N4 C12 C9 115.6(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O3 C5 O4 31.4(9) 2_856 . . . ?
Zn1 O3 C5 C4 -147.3(6) 2_856 . . . ?
Zn1 O4 C5 O3 -15.9(5) 1_545 . . . ?
Zn1 O4 C5 C4 162.7(2) 1_545 . . . ?
O3 C5 C4 C6 -177.7(3) . . . . ?
O4 C5 C4 C6 3.6(4) . . . . ?
O3 C5 C4 C3 5.0(4) . . . . ?
O4 C5 C4 C3 -173.7(3) . . . . ?
C3 C4 C6 C7 0.9(4) . . . . ?
C5 C4 C6 C7 -176.4(3) . . . . ?
C6 C4 C3 C2 -1.4(4) . . . . ?
C5 C4 C3 C2 175.9(2) . . . . ?
C7 N1 N2 C9 -177.3(3) . . . . ?
C4 C6 C7 C8 0.3(4) . . . . ?
C4 C6 C7 N1 178.6(3) . . . . ?
N2 N1 C7 C8 179.5(3) . . . . ?
N2 N1 C7 C6 1.2(4) . . . . ?
Zn1 O1 C1 O2 13.5(4) . . . . ?
Zn1 O1 C1 C2 -165.04(19) . . . . ?
C4 C3 C2 C8 0.8(4) . . . . ?
C4 C3 C2 C1 179.8(2) . . . . ?
O2 C1 C2 C8 -3.8(4) . . . . ?
O1 C1 C2 C8 174.9(3) . . . . ?
O2 C1 C2 C3 177.2(3) . . . . ?
O1 C1 C2 C3 -4.1(4) . . . . ?
C6 C7 C8 C2 -0.9(4) . . . . ?
N1 C7 C8 C2 -179.2(3) . . . . ?
C3 C2 C8 C7 0.4(4) . . . . ?
C1 C2 C8 C7 -178.6(3) . . . . ?
N1 N2 C9 C10 4.2(5) . . . . ?
N1 N2 C9 C12 -179.7(2) . . . . ?
N2 C9 C10 O5 -0.9(5) . . . . ?
C12 C9 C10 O5 -176.9(3) . . . . ?
N2 C9 C10 N3 178.8(3) . . . . ?
C12 C9 C10 N3 2.8(4) . . . . ?
O5 C10 N3 C11 -177.8(3) . . . . ?
C9 C10 N3 C11 2.5(5) . . . . ?
C10 N3 C11 O6 176.3(3) . . . . ?
C10 N3 C11 N4 -4.4(5) . . . . ?
C12 N4 C11 O6 -179.9(3) . . . . ?
C12 N4 C11 N3 0.9(4) . . . . ?
C11 N4 C12 O7 -176.4(3) . . . . ?
C11 N4 C12 C9 4.0(4) . . . . ?
N2 C9 C12 O7 -1.7(4) . . . . ?
C10 C9 C12 O7 174.7(3) . . . . ?
N2 C9 C12 N4 177.9(3) . . . . ?
C10 C9 C12 N4 -5.7(4) . . . . ?

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
O8 H8A O7 0.96 2.20 3.125(3) 160.7 1_665
O8 H8B O5 0.96 2.62 3.159(4) 115.6 1_655
O8 H8B O6 0.96 2.18 2.981(3) 140.5 2_665
N4 H4N O6 0.86 1.96 2.824(3) 178.7 2
O9 H9A O2 0.96 1.91 2.789(4) 151.4 2_766
O9 H9B O7 0.96 1.90 2.703(4) 139.8 2_756
N1 H1N O5 0.86 2.03 2.680(4) 131.7 .
N3 H3N O2 0.86 2.03 2.767(4) 143.0 2_665

_refine_diff_density_max         0.588
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.111

_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 1422596'
_audit_update_record             
;
2015-11-16 deposited with the CCDC.
2015-11-30 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            'C12 H10 Cd N4 O9'
_chemical_formula_weight         466.64

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      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                   7.8701(5)
_cell_length_b                   10.0231(6)
_cell_length_c                   10.5151(7)
_cell_angle_alpha                107.894(2)
_cell_angle_beta                 91.326(3)
_cell_angle_gamma                113.088(2)
_cell_volume                     716.27(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9657
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      26.40

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.164
_exptl_crystal_F_000             460
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    1.590
_shelx_estimated_absorpt_T_min   0.664
_shelx_estimated_absorpt_T_max   0.785
_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 PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11614
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_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         2.835
_diffrn_reflns_theta_max         26.394
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             2899
_reflns_number_gt                2808
_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)+(0.0526P)²+0.4349P] 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         2899
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0775
_refine_ls_wR_factor_gt          0.0768
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_restrained_S_all      1.132
_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
O4 O 1.1179(3) 0.8289(2) 0.4012(2) 0.0431(5) Uani 1 1 d . . . . .
O3 O 1.3693(3) 0.8124(3) 0.4702(3) 0.0483(6) Uani 1 1 d . . . . .
C8 C 1.2045(4) 0.7526(3) 0.4190(3) 0.0294(5) Uani 1 1 d . . . . .
C4 C 1.0958(3) 0.5799(3) 0.3695(3) 0.0269(5) Uani 1 1 d . . . . .
Cd1 Cd 1.32751(2) 0.06618(2) 0.43514(2) 0.02909(10) Uani 1 1 d . . . . .
O1 O 1.0681(3) 0.0750(2) 0.2968(2) 0.0413(5) Uani 1 1 d . . . . .
N1 N 0.6237(3) 0.2967(3) 0.1822(2) 0.0331(5) Uani 1 1 d . . . . .
H1N H 0.5561 0.1987 0.1492 0.040 Uiso 1 1 calc R U . . .
N2 N 0.5610(3) 0.3949(3) 0.1713(2) 0.0304(5) Uani 1 1 d . . . . .
O6 O -0.1090(3) 0.2827(2) -0.0719(2) 0.0380(5) Uani 1 1 d . . . . .
O7 O 0.4648(3) 0.6229(2) 0.1605(2) 0.0443(5) Uani 1 1 d . . . . .
O8 O 1.2823(3) 0.1098(3) 0.6616(2) 0.0485(6) Uani 1 1 d . . . . .
H8A H 1.2931 0.2133 0.7019 0.073 Uiso 1 1 d R U . . .
H8B H 1.1598 0.0378 0.6647 0.073 Uiso 1 1 d R U . . .
O9 O 1.4402(3) -0.0219(2) 0.2351(2) 0.0404(5) Uani 1 1 d . . . . .
H9A H 1.5338 -0.0549 0.2549 0.061 Uiso 1 1 d R U . . .
H9B H 1.3385 -0.1071 0.1696 0.061 Uiso 1 1 d R U . . .
C1 C 1.1556(4) 0.2180(3) 0.3515(3) 0.0305(5) Uani 1 1 d . . . . .
N3 N 0.0952(3) 0.1858(3) -0.0320(3) 0.0377(5) Uani 1 1 d . . . . .
H3N H 0.0163 0.0945 -0.0816 0.045 Uiso 1 1 calc R U . . .
N4 N 0.1818(3) 0.4499(3) 0.0448(2) 0.0333(5) Uani 1 1 d . . . . .
H4N H 0.1544 0.5256 0.0472 0.040 Uiso 1 1 calc R U . . .
O2 O 1.3128(3) 0.2806(3) 0.4251(3) 0.0511(6) Uani 1 1 d . . . . .
C2 C 1.0711(4) 0.3230(3) 0.3318(3) 0.0274(5) Uani 1 1 d . . . . .
C3 C 1.1760(4) 0.4833(3) 0.3851(3) 0.0276(5) Uani 1 1 d . . . . .
H3 H 1.2978 0.5247 0.4305 0.033 Uiso 1 1 calc R U . . .
C5 C 0.9115(4) 0.5180(3) 0.3040(3) 0.0284(5) Uani 1 1 d . . . . .
H5 H 0.8573 0.5830 0.2955 0.034 Uiso 1 1 calc R U . . .
C6 C 0.8091(4) 0.3583(3) 0.2513(3) 0.0273(5) Uani 1 1 d . . . . .
C9 C 0.3945(4) 0.3551(3) 0.1073(3) 0.0296(5) Uani 1 1 d . . . . .
C12 C 0.2602(4) 0.1987(3) 0.0309(3) 0.0325(6) Uani 1 1 d . . . . .
C11 C 0.0460(4) 0.3040(3) -0.0228(3) 0.0325(5) Uani 1 1 d . . . . .
C10 C 0.3552(4) 0.4873(3) 0.1085(3) 0.0311(5) Uani 1 1 d . . . . .
O5 O 0.2886(3) 0.0848(3) 0.0216(3) 0.0546(7) Uani 1 1 d . . . . .
C7 C 0.8874(4) 0.2602(3) 0.2636(3) 0.0285(5) Uani 1 1 d . . . . .
H7 H 0.8188 0.1537 0.2270 0.034 Uiso 1 1 calc R 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
O4 C8 1.255(3) . ?
O4 Cd1 2.209(2) 1_565 ?
O3 C8 1.221(4) . ?
O3 Cd1 2.244(2) 2_866 ?
C8 C4 1.504(3) . ?
C4 C3 1.391(4) . ?
C4 C5 1.396(4) . ?
Cd1 O4 2.209(2) 1_545 ?
Cd1 O2 2.231(2) . ?
Cd1 O3 2.244(2) 2_866 ?
Cd1 O8 2.347(2) . ?
Cd1 O9 2.356(2) . ?
Cd1 O1 2.525(2) . ?
Cd1 C1 2.702(3) . ?
O1 C1 1.249(3) . ?
N1 N2 1.294(3) . ?
N1 C6 1.416(3) . ?
N1 H1N 0.8600 . ?
N2 C9 1.309(4) . ?
O6 C11 1.225(4) . ?
O7 C10 1.221(3) . ?
O8 H8A 0.9600 . ?
O8 H8B 0.9600 . ?
O9 H9A 0.9600 . ?
O9 H9B 0.9600 . ?
C1 O2 1.254(4) . ?
C1 C2 1.507(4) . ?
N3 C11 1.362(4) . ?
N3 C12 1.385(3) . ?
N3 H3N 0.8600 . ?
N4 C10 1.362(4) . ?
N4 C11 1.373(3) . ?
N4 H4N 0.8600 . ?
C2 C3 1.401(4) . ?
C2 C7 1.400(4) . ?
C3 H3 0.9300 . ?
C5 C6 1.393(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.383(4) . ?
C9 C12 1.452(4) . ?
C9 C10 1.470(4) . ?
C12 O5 1.222(4) . ?
C7 H7 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
C8 O4 Cd1 107.52(17) . 1_565 ?
C8 O3 Cd1 177.2(2) . 2_866 ?
O3 C8 O4 122.9(3) . . ?
O3 C8 C4 120.7(3) . . ?
O4 C8 C4 116.4(2) . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 C8 121.7(2) . . ?
C5 C4 C8 117.9(2) . . ?
O4 Cd1 O2 134.38(8) 1_545 . ?
O4 Cd1 O3 131.04(9) 1_545 2_866 ?
O2 Cd1 O3 93.80(9) . 2_866 ?
O4 Cd1 O8 84.19(9) 1_545 . ?
O2 Cd1 O8 95.51(10) . . ?
O3 Cd1 O8 82.72(9) 2_866 . ?
O4 Cd1 O9 90.71(8) 1_545 . ?
O2 Cd1 O9 103.30(9) . . ?
O3 Cd1 O9 84.54(8) 2_866 . ?
O8 Cd1 O9 157.90(9) . . ?
O4 Cd1 O1 82.74(7) 1_545 . ?
O2 Cd1 O1 54.66(8) . . ?
O3 Cd1 O1 145.66(8) 2_866 . ?
O8 Cd1 O1 110.80(8) . . ?
O9 Cd1 O1 89.76(8) . . ?
O4 Cd1 C1 108.27(8) 1_545 . ?
O2 Cd1 C1 27.38(9) . . ?
O3 Cd1 C1 120.63(9) 2_866 . ?
O8 Cd1 C1 103.03(9) . . ?
O9 Cd1 C1 98.99(8) . . ?
O1 Cd1 C1 27.38(8) . . ?
C1 O1 Cd1 84.24(16) . . ?
N2 N1 C6 116.7(2) . . ?
N2 N1 H1N 121.6 . . ?
C6 N1 H1N 121.6 . . ?
N1 N2 C9 123.6(2) . . ?
Cd1 O8 H8A 109.4 . . ?
Cd1 O8 H8B 109.4 . . ?
H8A O8 H8B 109.5 . . ?
Cd1 O9 H9A 109.4 . . ?
Cd1 O9 H9B 109.3 . . ?
H9A O9 H9B 109.5 . . ?
O1 C1 O2 122.9(3) . . ?
O1 C1 C2 119.9(2) . . ?
O2 C1 C2 117.1(2) . . ?
O1 C1 Cd1 68.38(15) . . ?
O2 C1 Cd1 54.92(14) . . ?
C2 C1 Cd1 169.3(2) . . ?
C11 N3 C12 126.1(2) . . ?
C11 N3 H3N 117.0 . . ?
C12 N3 H3N 117.0 . . ?
C10 N4 C11 126.8(2) . . ?
C10 N4 H4N 116.6 . . ?
C11 N4 H4N 116.6 . . ?
C1 O2 Cd1 97.70(18) . . ?
C3 C2 C7 120.5(2) . . ?
C3 C2 C1 119.5(2) . . ?
C7 C2 C1 120.0(2) . . ?
C4 C3 C2 119.3(2) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C6 C5 C4 119.6(2) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C7 C6 C5 120.9(2) . . ?
C7 C6 N1 120.0(2) . . ?
C5 C6 N1 119.1(2) . . ?
N2 C9 C12 126.0(3) . . ?
N2 C9 C10 113.6(2) . . ?
C12 C9 C10 120.2(2) . . ?
O5 C12 N3 121.4(2) . . ?
O5 C12 C9 123.1(3) . . ?
N3 C12 C9 115.4(2) . . ?
O6 C11 N3 122.5(3) . . ?
O6 C11 N4 121.6(3) . . ?
N3 C11 N4 115.9(2) . . ?
O7 C10 N4 119.7(3) . . ?
O7 C10 C9 125.1(3) . . ?
N4 C10 C9 115.1(2) . . ?
C6 C7 C2 119.3(2) . . ?
C6 C7 H7 120.4 . . ?
C2 C7 H7 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cd1 O4 C8 O3 12.2(4) 1_565 . . . ?
Cd1 O4 C8 C4 -166.00(17) 1_565 . . . ?
O3 C8 C4 C3 2.7(4) . . . . ?
O4 C8 C4 C3 -179.1(3) . . . . ?
O3 C8 C4 C5 -175.9(3) . . . . ?
O4 C8 C4 C5 2.3(4) . . . . ?
C6 N1 N2 C9 178.2(2) . . . . ?
Cd1 O1 C1 O2 6.6(3) . . . . ?
Cd1 O1 C1 C2 -172.5(2) . . . . ?
O1 C1 O2 Cd1 -7.5(3) . . . . ?
C2 C1 O2 Cd1 171.6(2) . . . . ?
O1 C1 C2 C3 -175.3(3) . . . . ?
O2 C1 C2 C3 5.5(4) . . . . ?
Cd1 C1 C2 C3 45.4(11) . . . . ?
O1 C1 C2 C7 6.3(4) . . . . ?
O2 C1 C2 C7 -172.8(3) . . . . ?
Cd1 C1 C2 C7 -132.9(9) . . . . ?
C5 C4 C3 C2 1.4(4) . . . . ?
C8 C4 C3 C2 -177.1(2) . . . . ?
C7 C2 C3 C4 -0.1(4) . . . . ?
C1 C2 C3 C4 -178.5(2) . . . . ?
C3 C4 C5 C6 -1.5(4) . . . . ?
C8 C4 C5 C6 177.1(2) . . . . ?
C4 C5 C6 C7 0.3(4) . . . . ?
C4 C5 C6 N1 -178.6(2) . . . . ?
N2 N1 C6 C7 -178.2(2) . . . . ?
N2 N1 C6 C5 0.7(4) . . . . ?
N1 N2 C9 C12 -4.9(4) . . . . ?
N1 N2 C9 C10 -179.9(2) . . . . ?
C11 N3 C12 O5 176.7(3) . . . . ?
C11 N3 C12 C9 -3.4(4) . . . . ?
N2 C9 C12 O5 2.1(5) . . . . ?
C10 C9 C12 O5 176.8(3) . . . . ?
N2 C9 C12 N3 -177.9(3) . . . . ?
C10 C9 C12 N3 -3.1(4) . . . . ?
C12 N3 C11 O6 -173.6(3) . . . . ?
C12 N3 C11 N4 6.7(4) . . . . ?
C10 N4 C11 O6 176.8(3) . . . . ?
C10 N4 C11 N3 -3.5(4) . . . . ?
C11 N4 C10 O7 177.2(3) . . . . ?
C11 N4 C10 C9 -2.4(4) . . . . ?
N2 C9 C10 O7 1.5(4) . . . . ?
C12 C9 C10 O7 -173.9(3) . . . . ?
N2 C9 C10 N4 -178.9(2) . . . . ?
C12 C9 C10 N4 5.7(4) . . . . ?
C5 C6 C7 C2 0.9(4) . . . . ?
N1 C6 C7 C2 179.8(2) . . . . ?
C3 C2 C7 C6 -1.0(4) . . . . ?
C1 C2 C7 C6 177.3(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
N1 H1N O9 0.86 2.49 3.178(3) 137.0 1_455
N1 H1N O5 0.86 2.14 2.742(3) 126.7 .
O8 H8A O7 0.96 2.09 2.684(3) 118.3 2_766
O8 H8B O1 0.96 1.84 2.788(3) 169.2 2_756
O9 H9A O8 0.96 2.01 2.952(4) 167.2 2_856
O9 H9B O6 0.96 1.93 2.875(3) 167.6 2_655
N3 H3N O1 0.86 2.27 2.994(3) 142.4 2_655
N3 H3N O5 0.86 2.60 3.203(4) 127.9 2
N4 H4N O6 0.86 2.03 2.887(3) 173.8 2_565

_refine_diff_density_max         1.259
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.125

_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 1422597'
_audit_update_record             
;
2015-11-16 deposited with the CCDC.
2015-11-30 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            'C12 H18 N4 O13 Zn'
_chemical_formula_weight         491.67

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           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                   7.5088(5)
_cell_length_b                   13.6816(9)
_cell_length_c                   18.8063(12)
_cell_angle_alpha                90
_cell_angle_beta                 96.493(3)
_cell_angle_gamma                90
_cell_volume                     1919.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4235
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      25.35

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    1.357
_shelx_estimated_absorpt_T_min   0.671
_shelx_estimated_absorpt_T_max   0.764
_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 PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32059
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_av_R_equivalents  0.0798
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.180
_diffrn_reflns_theta_max         26.408
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3947
_reflns_number_gt                2844
_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)+(0.0498P)²+2.7467P] 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         3947
_refine_ls_number_parameters     289
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1156
_refine_ls_wR_factor_gt          0.1015
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.38131(6) 0.22507(3) 0.24614(2) 0.03244(15) Uani 1 1 d . . . . .
O6 O 0.3292(4) 0.37555(19) 0.34994(14) 0.0505(8) Uani 1 1 d . . . . .
O11 O 0.6823(4) 0.52920(19) 0.45723(15) 0.0416(7) Uani 1 1 d D . . . .
O12 O 0.8008(5) 0.4383(2) 0.61268(16) 0.0589(9) Uani 1 1 d D . . . .
O3 O 1.1499(4) -0.13348(18) 0.74930(12) 0.0376(6) Uani 1 1 d . . . . .
H3O H 1.2541 -0.1219 0.7551 0.056 Uiso 1 1 d R U . . .
O4 O 1.0994(5) 0.0226(2) 0.72454(16) 0.0568(9) Uani 1 1 d . . . . .
O13 O 0.8352(5) 0.0803(3) 0.80877(18) 0.0612(9) Uani 1 1 d D . . . .
O2 O 1.0971(4) -0.36473(19) 0.54526(14) 0.0486(8) Uani 1 1 d . . . . .
O1 O 0.9310(4) -0.32513(17) 0.44404(12) 0.0341(6) Uani 1 1 d . . . . .
O5 O 0.5420(3) 0.06721(16) 0.36278(12) 0.0298(6) Uani 1 1 d . . . . .
N3 N 0.4382(4) 0.22254(19) 0.35316(14) 0.0242(6) Uani 1 1 d . . . . .
N4 N 0.4548(4) 0.32142(19) 0.45697(14) 0.0259(6) Uani 1 1 d . . . . .
H4N H 0.4301 0.3768 0.4751 0.031 Uiso 1 1 calc R U . . .
N2 N 0.6692(4) 0.09871(18) 0.51025(14) 0.0209(6) Uani 1 1 d . . . . .
N1 N 0.7114(4) 0.01469(18) 0.48439(14) 0.0221(6) Uani 1 1 d . . . . .
H1N H 0.6722 -0.0008 0.4411 0.026 Uiso 1 1 calc R U . . .
C11 C 0.4049(5) 0.3088(2) 0.38462(17) 0.0280(8) Uani 1 1 d . . . . .
C10 C 0.5393(5) 0.2545(2) 0.50220(17) 0.0222(7) Uani 1 1 d . . . . .
C9 C 0.5767(4) 0.1616(2) 0.46811(16) 0.0199(7) Uani 1 1 d . . . . .
C7 C 0.8212(4) -0.0509(2) 0.52709(16) 0.0199(7) Uani 1 1 d . . . . .
C8 C 0.8535(4) -0.1417(2) 0.49829(16) 0.0211(7) Uani 1 1 d . . . . .
H8 H 0.8034 -0.1575 0.4522 0.025 Uiso 1 1 calc R U . . .
C2 C 0.9609(4) -0.2091(2) 0.53840(17) 0.0209(7) Uani 1 1 d . . . . .
C3 C 1.0343(4) -0.1846(2) 0.60701(16) 0.0213(7) Uani 1 1 d . . . . .
H3 H 1.1035 -0.2301 0.6346 0.026 Uiso 1 1 calc R U . . .
C4 C 1.0052(4) -0.0922(2) 0.63501(16) 0.0215(7) Uani 1 1 d . . . . .
C6 C 0.8969(4) -0.0257(2) 0.59518(17) 0.0225(7) Uani 1 1 d . . . . .
H6 H 0.8751 0.0354 0.6140 0.027 Uiso 1 1 calc R U . . .
C5 C 1.0913(5) -0.0654(3) 0.70855(17) 0.0288(8) Uani 1 1 d . . . . .
C1 C 1.0001(5) -0.3071(2) 0.50700(18) 0.0262(7) Uani 1 1 d . . . . .
C12 C 0.5179(4) 0.1471(2) 0.39175(16) 0.0208(7) Uani 1 1 d . . . . .
O7 O 0.5756(4) 0.27316(17) 0.56587(12) 0.0349(6) Uani 1 1 d . . . . .
O9 O 0.5431(6) 0.3269(3) 0.20654(19) 0.0868(13) Uani 1 1 d . . . . .
H9A H 0.5796 0.3035 0.1623 0.130 Uiso 1 1 d R U . . .
H9B H 0.6470 0.3371 0.2404 0.130 Uiso 1 1 d R U . . .
O10 O 0.1311(4) 0.2643(2) 0.20573(16) 0.0541(8) Uani 1 1 d . . . . .
H10A H 0.0456 0.2273 0.2289 0.081 Uiso 1 1 d R U . . .
H10B H 0.1143 0.3327 0.2140 0.081 Uiso 1 1 d R U . . .
O8 O 0.4332(5) 0.0926(2) 0.20568(18) 0.0645(9) Uani 1 1 d . . . . .
H8A H 0.4337 0.0980 0.1548 0.097 Uiso 1 1 d R U . . .
H8B H 0.3420 0.0472 0.2159 0.097 Uiso 1 1 d R U . . .
H13A H 0.932(5) 0.070(5) 0.787(3) 0.097 Uiso 1 1 d D U . . .
H13B H 0.869(8) 0.102(4) 0.8530(16) 0.097 Uiso 1 1 d D U . . .
H12B H 0.769(8) 0.5041(19) 0.614(3) 0.097 Uiso 1 1 d D U . . .
H12A H 0.817(8) 0.413(4) 0.6587(16) 0.097 Uiso 1 1 d D U . . .
H11A H 0.742(7) 0.474(3) 0.460(3) 0.097 Uiso 1 1 d D U . . .
H11B H 0.765(6) 0.574(3) 0.454(3) 0.097 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 N3 2.010(3) . ?
Zn1 O10 2.018(3) . ?
Zn1 O8 2.021(3) . ?
Zn1 O9 2.043(4) . ?
O6 C11 1.224(4) . ?
O11 H11A 0.88(2) . ?
O11 H11B 0.88(2) . ?
O12 H12B 0.93(2) . ?
O12 H12A 0.93(2) . ?
O3 C5 1.254(4) . ?
O3 H3O 0.7934 . ?
O4 C5 1.240(4) . ?
O13 H13A 0.89(2) . ?
O13 H13B 0.89(2) . ?
O2 C1 1.245(4) . ?
O5 C12 1.243(4) . ?
N3 C11 1.356(4) . ?
N3 C12 1.361(4) . ?
N4 C10 1.358(4) . ?
N4 C11 1.381(4) . ?
N4 H4N 0.8600 . ?
N2 N1 1.301(4) . ?
N2 C9 1.314(4) . ?
N1 C7 1.407(4) . ?
N1 H1N 0.8600 . ?
C10 O7 1.225(4) . ?
C10 C9 1.465(4) . ?
C9 C12 1.467(4) . ?
C7 C6 1.385(4) . ?
C7 C8 1.387(4) . ?
C8 C2 1.390(4) . ?
C8 H8 0.9300 . ?
C2 C3 1.386(4) . ?
C2 C1 1.508(4) . ?
C3 C4 1.397(4) . ?
C3 H3 0.9300 . ?
C4 C6 1.382(4) . ?
C4 C5 1.504(4) . ?
C6 H6 0.9300 . ?
O9 H9A 0.9600 . ?
O9 H9B 0.9600 . ?
O10 H10A 0.9600 . ?
O10 H10B 0.9600 . ?
O8 H8A 0.9600 . ?
O8 H8B 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
N3 Zn1 O10 117.72(12) . . ?
N3 Zn1 O8 109.47(12) . . ?
O10 Zn1 O8 107.91(13) . . ?
N3 Zn1 O9 107.99(13) . . ?
O10 Zn1 O9 104.37(16) . . ?
O8 Zn1 O9 109.04(17) . . ?
H11A O11 H11B 105(5) . . ?
H12B O12 H12A 110(5) . . ?
C5 O3 H3O 102.0 . . ?
H13A O13 H13B 109(6) . . ?
C11 N3 C12 121.3(3) . . ?
C11 N3 Zn1 113.1(2) . . ?
C12 N3 Zn1 125.3(2) . . ?
C10 N4 C11 126.1(3) . . ?
C10 N4 H4N 117.0 . . ?
C11 N4 H4N 117.0 . . ?
N1 N2 C9 119.2(3) . . ?
N2 N1 C7 120.1(3) . . ?
N2 N1 H1N 119.9 . . ?
C7 N1 H1N 119.9 . . ?
O6 C11 N3 121.0(3) . . ?
O6 C11 N4 119.3(3) . . ?
N3 C11 N4 119.7(3) . . ?
O7 C10 N4 120.5(3) . . ?
O7 C10 C9 125.2(3) . . ?
N4 C10 C9 114.2(3) . . ?
N2 C9 C10 114.8(3) . . ?
N2 C9 C12 125.6(3) . . ?
C10 C9 C12 119.6(3) . . ?
C6 C7 C8 120.8(3) . . ?
C6 C7 N1 121.5(3) . . ?
C8 C7 N1 117.7(3) . . ?
C7 C8 C2 119.9(3) . . ?
C7 C8 H8 120.1 . . ?
C2 C8 H8 120.1 . . ?
C3 C2 C8 119.4(3) . . ?
C3 C2 C1 120.3(3) . . ?
C8 C2 C1 120.3(3) . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C6 C4 C3 119.9(3) . . ?
C6 C4 C5 120.2(3) . . ?
C3 C4 C5 119.9(3) . . ?
C4 C6 C7 119.5(3) . . ?
C4 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
O4 C5 O3 124.7(3) . . ?
O4 C5 C4 117.6(3) . . ?
O3 C5 C4 117.7(3) . . ?
O2 C1 C2 117.6(3) . . ?
O5 C12 N3 120.7(3) . . ?
O5 C12 C9 120.4(3) . . ?
N3 C12 C9 119.0(3) . . ?
Zn1 O9 H9A 109.2 . . ?
Zn1 O9 H9B 109.2 . . ?
H9A O9 H9B 109.5 . . ?
Zn1 O10 H10A 109.3 . . ?
Zn1 O10 H10B 109.4 . . ?
H10A O10 H10B 109.5 . . ?
Zn1 O8 H8A 109.2 . . ?
Zn1 O8 H8B 109.4 . . ?
H8A O8 H8B 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
C9 N2 N1 C7 175.5(3) . . . . ?
C12 N3 C11 O6 -178.2(4) . . . . ?
Zn1 N3 C11 O6 7.5(5) . . . . ?
C12 N3 C11 N4 1.0(5) . . . . ?
Zn1 N3 C11 N4 -173.3(3) . . . . ?
C10 N4 C11 O6 -180.0(4) . . . . ?
C10 N4 C11 N3 0.8(6) . . . . ?
C11 N4 C10 O7 -179.2(3) . . . . ?
C11 N4 C10 C9 -0.3(5) . . . . ?
N1 N2 C9 C10 -178.9(3) . . . . ?
N1 N2 C9 C12 -1.6(5) . . . . ?
O7 C10 C9 N2 -5.6(5) . . . . ?
N4 C10 C9 N2 175.6(3) . . . . ?
O7 C10 C9 C12 177.0(3) . . . . ?
N4 C10 C9 C12 -1.9(4) . . . . ?
N2 N1 C7 C6 -4.6(5) . . . . ?
N2 N1 C7 C8 176.4(3) . . . . ?
C6 C7 C8 C2 1.0(5) . . . . ?
N1 C7 C8 C2 -179.9(3) . . . . ?
C7 C8 C2 C3 0.1(5) . . . . ?
C7 C8 C2 C1 -178.7(3) . . . . ?
C8 C2 C3 C4 -1.8(5) . . . . ?
C1 C2 C3 C4 177.0(3) . . . . ?
C2 C3 C4 C6 2.5(5) . . . . ?
C2 C3 C4 C5 -177.8(3) . . . . ?
C3 C4 C6 C7 -1.3(5) . . . . ?
C5 C4 C6 C7 178.9(3) . . . . ?
C8 C7 C6 C4 -0.4(5) . . . . ?
N1 C7 C6 C4 -179.4(3) . . . . ?
C6 C4 C5 O4 -17.5(5) . . . . ?
C3 C4 C5 O4 162.7(4) . . . . ?
C6 C4 C5 O3 162.6(3) . . . . ?
C3 C4 C5 O3 -17.2(5) . . . . ?
C3 C2 C1 O2 1.2(5) . . . . ?
C8 C2 C1 O2 180.0(3) . . . . ?
C11 N3 C12 O5 177.4(3) . . . . ?
Zn1 N3 C12 O5 -9.1(5) . . . . ?
C11 N3 C12 C9 -3.1(5) . . . . ?
Zn1 N3 C12 C9 170.4(2) . . . . ?
N2 C9 C12 O5 5.9(5) . . . . ?
C10 C9 C12 O5 -176.9(3) . . . . ?
N2 C9 C12 N3 -173.6(3) . . . . ?
C10 C9 C12 N3 3.6(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
O11 H11B O1 0.88(2) 1.88(2) 2.762(4) 176(6) 1_565
O11 H11A O2 0.88(2) 1.93(2) 2.798(4) 169(6) 3_756
O12 H12A O3 0.93(2) 1.83(2) 2.761(4) 178(6) 2_756
O12 H12B O6 0.93(2) 1.95(3) 2.844(4) 159(5) 3_666
O13 H13B O2 0.89(2) 1.96(2) 2.836(4) 169(6) 2_756
O13 H13A O4 0.89(2) 1.92(3) 2.789(5) 164(6) .
O8 H8B O13 0.96 2.21 3.100(5) 153.4 3_656
O8 H8A O11 0.96 2.38 3.208(4) 144.0 2_645
O10 H10B O4 0.96 1.99 2.951(4) 174.0 4_465
O10 H10A O3 0.96 2.03 2.962(4) 164.3 3_656
O9 H9B O13 0.96 2.13 3.027(5) 156.0 4_565
O9 H9A O7 0.96 2.09 3.013(4) 160.2 4_565
N1 H1N O5 0.86 1.91 2.590(3) 134.4 .
N4 H4N O11 0.86 2.06 2.866(4) 156.7 3_666
O3 H3O O8 0.79 2.41 3.198(4) 170.0 3_756
O11 H11B O1 0.88(2) 1.88(2) 2.762(4) 176(6) 1_565
O11 H11A O2 0.88(2) 1.93(2) 2.798(4) 169(6) 3_756
O12 H12A O3 0.93(2) 1.83(2) 2.761(4) 178(6) 2_756
O12 H12B O6 0.93(2) 1.95(3) 2.844(4) 159(5) 3_666
O13 H13B O2 0.89(2) 1.96(2) 2.836(4) 169(6) 2_756
O13 H13A O4 0.89(2) 1.92(3) 2.789(5) 164(6) .
O8 H8B O13 0.96 2.21 3.100(5) 153.4 3_656
O8 H8A O11 0.96 2.38 3.208(4) 144.0 2_645
O10 H10B O4 0.96 1.99 2.951(4) 174.0 4_465
O10 H10A O3 0.96 2.03 2.962(4) 164.3 3_656
O9 H9B O13 0.96 2.13 3.027(5) 156.0 4_565
O9 H9A O7 0.96 2.09 3.013(4) 160.2 4_565
N1 H1N O5 0.86 1.91 2.590(3) 134.4 .
N4 H4N O11 0.86 2.06 2.866(4) 156.7 3_666
O3 H3O O8 0.79 2.41 3.198(4) 170.0 3_756

_refine_diff_density_max         0.635
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.097

_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 1422598'
_audit_update_record             
;
2015-11-16 deposited with the CCDC.
2015-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 Cd N4 O10, 4(H2 O)'
_chemical_formula_sum            'C12 H20 Cd N4 O14'
_chemical_formula_weight         556.72

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           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                   22.127(4)
_cell_length_b                   15.583(4)
_cell_length_c                   14.931(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.340(10)
_cell_angle_gamma                90
_cell_volume                     4940.4(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9994
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      25.78

_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_F_000             2240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.950
_shelx_estimated_absorpt_T_min   0.770
_shelx_estimated_absorpt_T_max   0.848
_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 PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34149
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.327
_diffrn_reflns_theta_max         25.909
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             4726
_reflns_number_gt                3054
_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)+(0.1025P)²] 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         4726
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0580
_refine_ls_wR_factor_ref         0.1734
_refine_ls_wR_factor_gt          0.1601
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.000 0.013 845 121 ' '
2 1.000 0.500 -0.004 845 121 ' '
_platon_squeeze_details          
;
 The Platon SQUEEZE procedure was applied to recover 242 electrons per
 unit cell in a void (total volume 1690 A^3), that is, 30.2 electrons
 per formula unit. On the basis of microanalytical data, the void content
 may include 3 water molecules, i.e., a total of 30 electrons not
 far from the values estimated by SQUEEZE. 
 PLATON Reference : Spek, A.L. (2003), J.Appl.Cryst. 36, 7-13.
;

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
O1 O 0.3162(2) 0.3087(2) 0.4236(3) 0.0752(11) Uani 1 1 d . . . . .
O2 O 0.26033(19) 0.4163(2) 0.3489(3) 0.0721(10) Uani 1 1 d . . . . .
C8 C 0.3077(3) 0.3884(3) 0.4080(3) 0.0560(13) Uani 1 1 d . . . . .
Cd1 Cd 0.71444(2) 0.22518(2) 0.81226(3) 0.0692(2) Uani 1 1 d . . . . .
O5 O 0.77544(19) 0.4048(3) 0.9083(3) 0.0790(11) Uani 1 1 d . . . . .
O6 O 0.63922(17) 0.61757(19) 0.7855(3) 0.0644(9) Uani 1 1 d . . . . .
O7 O 0.58697(18) 0.3265(2) 0.7147(3) 0.0725(11) Uani 1 1 d . . . . .
N1 N 0.51143(17) 0.4495(2) 0.6375(2) 0.0480(9) Uani 1 1 d . . . . .
H1 H 0.5182 0.3952 0.6437 0.058 Uiso 1 1 calc R U . . .
O4 O 0.3200(2) 0.7130(2) 0.4560(3) 0.0871(13) Uani 1 1 d . . . . .
H4O H 0.3177 0.7655 0.4524 0.131 Uiso 1 1 calc R U . . .
O3 O 0.4209(2) 0.7408(3) 0.5173(5) 0.1111(18) Uani 1 1 d . . . . .
O8 O 0.7770(2) 0.2587(3) 0.7135(3) 0.0849(12) Uani 1 1 d . . . . .
H8A H 0.7505 0.2777 0.6543 0.127 Uiso 1 1 d R U . . .
H8B H 0.7998 0.2085 0.7046 0.127 Uiso 1 1 d R U . . .
N3 N 0.6828(2) 0.3623(2) 0.8092(3) 0.0519(10) Uani 1 1 d . . . . .
N4 N 0.70484(18) 0.5086(2) 0.8475(3) 0.0522(10) Uani 1 1 d . . . . .
H4 H 0.7311 0.5452 0.8800 0.063 Uiso 1 1 calc R U . . .
C4 C 0.3559(2) 0.4502(3) 0.4634(3) 0.0439(10) Uani 1 1 d . . . . .
O10 O 0.6414(2) 0.1544(3) 0.6973(3) 0.1056(15) Uani 1 1 d . . . . .
H10A H 0.6008 0.1790 0.6922 0.158 Uiso 1 1 d R U . . .
H10B H 0.6511 0.1603 0.6388 0.158 Uiso 1 1 d R U . . .
O9 O 0.6640(2) 0.1931(3) 0.9260(3) 0.0932(14) Uani 1 1 d . . . . .
H9A H 0.6933 0.1663 0.9785 0.140 Uiso 1 1 d R U . . .
H9B H 0.6485 0.2452 0.9459 0.140 Uiso 1 1 d R U . . .
C11 C 0.7224(3) 0.4240(3) 0.8566(4) 0.0572(13) Uani 1 1 d . . . . .
C12 C 0.6499(2) 0.5400(3) 0.7918(3) 0.0487(11) Uani 1 1 d . . . . .
C9 C 0.6057(2) 0.4739(3) 0.7419(3) 0.0433(10) Uani 1 1 d . . . . .
C10 C 0.6240(2) 0.3841(3) 0.7552(3) 0.0510(12) Uani 1 1 d . . . . .
N2 N 0.55283(18) 0.5031(2) 0.6857(3) 0.0446(9) Uani 1 1 d . . . . .
C6 C 0.4554(2) 0.4804(3) 0.5751(3) 0.0419(10) Uani 1 1 d . . . . .
C5 C 0.4111(2) 0.4212(3) 0.5251(3) 0.0456(11) Uani 1 1 d . . . . .
H5 H 0.4187 0.3627 0.5334 0.055 Uiso 1 1 calc R U . . .
C3 C 0.3450(2) 0.5371(3) 0.4520(3) 0.0491(11) Uani 1 1 d . . . . .
H3 H 0.3076 0.5562 0.4108 0.059 Uiso 1 1 calc R U . . .
C2 C 0.3889(2) 0.5971(3) 0.5009(3) 0.0494(11) Uani 1 1 d . . . . .
C7 C 0.4451(2) 0.5678(3) 0.5618(3) 0.0481(11) Uani 1 1 d . . . . .
H7 H 0.4755 0.6067 0.5934 0.058 Uiso 1 1 calc R U . . .
C1 C 0.3761(3) 0.6913(3) 0.4899(4) 0.0655(15) Uani 1 1 d . . . . .
O11 O 0.2778(2) 0.8719(3) 0.4847(3) 0.0955(14) Uani 1 1 d . . . . .
H11A H 0.2852 0.9345 0.4946 0.143 Uiso 1 1 d . U . . .
H11B H 0.2599 0.8409 0.5192 0.143 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
O1 C8 1.268(7) . ?
O1 Cd1 2.450(4) 8_455 ?
O2 C8 1.244(6) . ?
O2 Cd1 2.425(4) 8_455 ?
C8 C4 1.500(7) . ?
Cd1 N3 2.246(4) . ?
Cd1 O10 2.284(5) . ?
Cd1 O9 2.334(4) . ?
Cd1 O8 2.348(5) . ?
Cd1 O2 2.425(4) 8_556 ?
Cd1 O1 2.450(4) 8_556 ?
O5 C11 1.246(6) . ?
O6 C12 1.229(5) . ?
O7 C10 1.250(6) . ?
N1 N2 1.297(5) . ?
N1 C6 1.410(6) . ?
N1 H1 0.8600 . ?
O4 C1 1.249(7) . ?
O4 H4O 0.8200 . ?
O3 C1 1.232(7) . ?
O8 H8A 0.9600 . ?
O8 H8B 0.9600 . ?
N3 C10 1.366(6) . ?
N3 C11 1.358(7) . ?
N4 C12 1.357(6) . ?
N4 C11 1.371(6) . ?
N4 H4 0.8600 . ?
C4 C3 1.377(6) . ?
C4 C5 1.382(6) . ?
O10 H10A 0.9600 . ?
O10 H10B 0.9600 . ?
O9 H9A 0.9600 . ?
O9 H9B 0.9600 . ?
C12 C9 1.471(7) . ?
C9 N2 1.314(6) . ?
C9 C10 1.455(6) . ?
C6 C7 1.385(6) . ?
C6 C5 1.399(6) . ?
C5 H5 0.9300 . ?
C3 C2 1.398(7) . ?
C3 H3 0.9300 . ?
C2 C7 1.396(7) . ?
C2 C1 1.495(7) . ?
C7 H7 0.9300 . ?
O11 H11A 0.99000 . ?
O11 H11B 0.88000 . ?

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
C8 O1 Cd1 91.5(3) . 8_455 ?
C8 O2 Cd1 93.3(3) . 8_455 ?
O2 C8 O1 121.6(5) . . ?
O2 C8 C4 119.6(5) . . ?
O1 C8 C4 118.8(5) . . ?
N3 Cd1 O10 107.07(17) . . ?
N3 Cd1 O9 90.48(15) . . ?
O10 Cd1 O9 93.5(2) . . ?
N3 Cd1 O8 90.67(15) . . ?
O10 Cd1 O8 93.04(19) . . ?
O9 Cd1 O8 172.72(17) . . ?
N3 Cd1 O2 168.10(14) . 8_556 ?
O10 Cd1 O2 83.87(15) . 8_556 ?
O9 Cd1 O2 84.06(15) . 8_556 ?
O8 Cd1 O2 93.45(15) . 8_556 ?
N3 Cd1 O1 116.15(14) . 8_556 ?
O10 Cd1 O1 136.62(16) . 8_556 ?
O9 Cd1 O1 89.77(16) . 8_556 ?
O8 Cd1 O1 83.26(15) . 8_556 ?
O2 Cd1 O1 53.46(13) 8_556 8_556 ?
N2 N1 C6 120.0(4) . . ?
N2 N1 H1 120.0 . . ?
C6 N1 H1 120.0 . . ?
C1 O4 H4O 109.5 . . ?
Cd1 O8 H8A 109.3 . . ?
Cd1 O8 H8B 109.4 . . ?
H8A O8 H8B 109.5 . . ?
C10 N3 C11 120.0(4) . . ?
C10 N3 Cd1 119.2(3) . . ?
C11 N3 Cd1 120.7(3) . . ?
C12 N4 C11 126.0(4) . . ?
C12 N4 H4 117.0 . . ?
C11 N4 H4 117.0 . . ?
C3 C4 C5 119.7(4) . . ?
C3 C4 C8 119.3(4) . . ?
C5 C4 C8 121.0(4) . . ?
Cd1 O10 H10A 108.4 . . ?
Cd1 O10 H10B 110.2 . . ?
H10A O10 H10B 109.5 . . ?
Cd1 O9 H9A 109.6 . . ?
Cd1 O9 H9B 109.2 . . ?
H9A O9 H9B 109.5 . . ?
O5 C11 N3 120.7(5) . . ?
O5 C11 N4 118.9(5) . . ?
N3 C11 N4 120.4(5) . . ?
O6 C12 N4 121.4(5) . . ?
O6 C12 C9 124.4(5) . . ?
N4 C12 C9 114.3(4) . . ?
N2 C9 C10 125.8(4) . . ?
N2 C9 C12 115.2(4) . . ?
C10 C9 C12 119.0(4) . . ?
O7 C10 N3 119.5(4) . . ?
O7 C10 C9 120.3(4) . . ?
N3 C10 C9 120.1(4) . . ?
C9 N2 N1 119.6(4) . . ?
C7 C6 C5 120.6(4) . . ?
C7 C6 N1 120.6(4) . . ?
C5 C6 N1 118.8(4) . . ?
C4 C5 C6 119.7(4) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C4 C3 C2 121.4(4) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C2 C7 118.8(4) . . ?
C3 C2 C1 121.2(5) . . ?
C7 C2 C1 119.9(4) . . ?
C6 C7 C2 119.7(4) . . ?
C6 C7 H7 120.1 . . ?
C2 C7 H7 120.1 . . ?
O3 C1 O4 125.4(5) . . ?
O3 C1 C2 118.0(5) . . ?
O4 C1 C2 116.5(5) . . ?
H11A O11 H11B 122.00 . . ?

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 O2 C8 O1 2.8(5) 8_455 . . . ?
Cd1 O2 C8 C4 -176.4(4) 8_455 . . . ?
Cd1 O1 C8 O2 -2.8(5) 8_455 . . . ?
Cd1 O1 C8 C4 176.4(4) 8_455 . . . ?
O2 C8 C4 C3 4.0(7) . . . . ?
O1 C8 C4 C3 -175.2(4) . . . . ?
O2 C8 C4 C5 -175.7(4) . . . . ?
O1 C8 C4 C5 5.1(7) . . . . ?
C10 N3 C11 O5 177.9(5) . . . . ?
Cd1 N3 C11 O5 -5.4(7) . . . . ?
C10 N3 C11 N4 -2.8(7) . . . . ?
Cd1 N3 C11 N4 173.9(3) . . . . ?
C12 N4 C11 O5 177.6(5) . . . . ?
C12 N4 C11 N3 -1.6(8) . . . . ?
C11 N4 C12 O6 -177.2(5) . . . . ?
C11 N4 C12 C9 3.1(7) . . . . ?
O6 C12 C9 N2 2.2(7) . . . . ?
N4 C12 C9 N2 -178.2(4) . . . . ?
O6 C12 C9 C10 179.8(4) . . . . ?
N4 C12 C9 C10 -0.6(6) . . . . ?
C11 N3 C10 O7 -177.2(5) . . . . ?
Cd1 N3 C10 O7 6.1(6) . . . . ?
C11 N3 C10 C9 5.2(7) . . . . ?
Cd1 N3 C10 C9 -171.5(3) . . . . ?
N2 C9 C10 O7 -3.7(7) . . . . ?
C12 C9 C10 O7 178.9(4) . . . . ?
N2 C9 C10 N3 173.9(4) . . . . ?
C12 C9 C10 N3 -3.5(6) . . . . ?
C10 C9 N2 N1 1.4(7) . . . . ?
C12 C9 N2 N1 178.8(4) . . . . ?
C6 N1 N2 C9 -178.3(4) . . . . ?
N2 N1 C6 C7 2.6(6) . . . . ?
N2 N1 C6 C5 -179.0(4) . . . . ?
C3 C4 C5 C6 -0.2(6) . . . . ?
C8 C4 C5 C6 179.4(4) . . . . ?
C7 C6 C5 C4 -1.4(6) . . . . ?
N1 C6 C5 C4 -179.8(4) . . . . ?
C5 C4 C3 C2 0.6(7) . . . . ?
C8 C4 C3 C2 -179.1(4) . . . . ?
C4 C3 C2 C7 0.6(7) . . . . ?
C4 C3 C2 C1 -178.6(5) . . . . ?
C5 C6 C7 C2 2.7(7) . . . . ?
N1 C6 C7 C2 -178.9(4) . . . . ?
C3 C2 C7 C6 -2.3(7) . . . . ?
C1 C2 C7 C6 177.0(4) . . . . ?
C3 C2 C1 O3 -164.0(6) . . . . ?
C7 C2 C1 O3 16.8(8) . . . . ?
C3 C2 C1 O4 18.2(8) . . . . ?
C7 C2 C1 O4 -161.0(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 O7 0.86 1.92 2.591(5) 134.0 .
O4 H4O O11 0.82 2.00 2.722(6) 146.6 .
O8 H8A O4 0.96 1.93 2.855(7) 161.3 5_666
O8 H8B O6 0.96 1.93 2.873(5) 165.7 4_646
N4 H4 O11 0.86 2.07 2.899(6) 163.0 8_566
O10 H10A O7 0.96 2.36 2.982(6) 122.3 .
O10 H10B O4 0.96 2.61 3.367(7) 135.8 5_666
O9 H9A O5 0.96 1.98 2.894(6) 159.2 7_657
O9 H9B O1 0.96 2.13 2.815(6) 127.2 2_656

_refine_diff_density_max         1.007
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.105

_shelxl_version_number           2014/6

