# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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 1017331'
_audit_update_record             
;
2014-07-31 deposited with the CCDC.
2015-01-05 downloaded from the CCDC.
;
_audit_creation_date             2014-03-05
_audit_creation_method           
;
Olex2 1.2-ac21
(compiled 2014.02.17 svn.r2891 for OlexSys, GUI svn.r3563)
;
_shelxl_version_number           2013-2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C6 H7 N3 O4, H2 O'
_chemical_formula_sum            'C6 H9 N3 O5'
_chemical_formula_weight         203.16
_chemical_melting_point          ?
_exptl_crystal_description       needle
_exptl_crystal_colour            'clear colourless'
_diffrn_ambient_temperature      296(2)
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.3766(8)
_cell_length_b                   6.2427(6)
_cell_length_c                   17.4768(17)
_cell_angle_alpha                90
_cell_angle_beta                 102.314(6)
_cell_angle_gamma                90
_cell_volume                     892.88(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3231
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.995
_cell_measurement_theta_min      2.386
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.6982
_exptl_absorpt_correction_T_min  0.6492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7970
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_min         2.386
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'ω scans and φ scans'
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1480
_reflns_number_total             1753
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       'Bruker Smart Apex II'
_computing_data_reduction        'Bruker SAINT (2001)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         1753
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0495
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0773P)²+0.2716P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1397
_refine_ls_wR_factor_ref         0.1490
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 N1B-C1 \\sim N1B-C1
 with sigma of 0.001
 N1B-O1B \\sim N1A-O1A
 with sigma of 0.001
 N1B-C1 \\sim N1A-C1
 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(N1A) = Uanis(N1B)
4. Others
 Uiso(H3A)=Uiso(H3B)=Uiso(H3C)=FVAR(1)
 Uiso(H5A)=Uiso(H5B)=Uiso(H5C)=FVAR(2)
 Sof(O1B)=Sof(H1B)=Sof(N1B)=1-FVAR(3)
 Sof(O1A)=Sof(H1A)=Sof(N1A)=FVAR(3)
5.a Riding coordinates:
 O1A(H1A), O1B(H1B), O5(H5D,H5E)
5.b Rotating group:
 C3(H3A,H3B,H3C), C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
O1A O 0.6137(3) 0.8615(4) 0.45664(16) 0.0720(8) Uani 0.579(3) 1 d . . P A 1
H1A H 0.6393 0.9691 0.4833 0.108 Uiso 0.579(3) 1 d R . P A 1
O1B O 0.8089(5) 0.8640(7) 0.4657(2) 0.0731(12) Uani 0.421(3) 1 d . . P A 2
H1B H 0.7815 0.9729 0.4858 0.110 Uiso 0.421(3) 1 d R . P A 2
O2 O 1.00322(18) 0.5811(3) 0.41164(11) 0.0861(5) Uani 1 1 d . . . . .
O3 O 0.72208(17) 0.0261(2) 0.28649(8) 0.0668(4) Uani 1 1 d . . . . .
O4 O 0.42775(19) 0.5521(3) 0.36618(12) 0.0962(6) Uani 1 1 d . . . . .
N1A N 0.7480(4) 0.7605(5) 0.4430(2) 0.0574(8) Uani 0.579(3) 1 d . . P A 1
N1B N 0.6699(4) 0.7588(6) 0.4326(3) 0.0574(8) Uani 0.421(3) 1 d . . P A 2
N2 N 0.86414(17) 0.2890(2) 0.35999(8) 0.0517(4) Uani 1 1 d . . . . .
N3 N 0.57438(17) 0.2866(3) 0.32840(9) 0.0542(4) Uani 1 1 d . . . . .
C1 C 0.7163(2) 0.5850(3) 0.40047(10) 0.0542(5) Uani 1 1 d . . . . .
C2 C 0.8731(2) 0.4911(3) 0.39176(10) 0.0561(5) Uani 1 1 d . . . . .
C3 C 1.0150(2) 0.1833(4) 0.35133(14) 0.0775(7) Uani 1 1 d . . . . .
H3A H 1.0067 0.0322 0.3600 0.130(6) Uiso 1 1 d GR . . . .
H3B H 1.1054 0.2410 0.3889 0.130(6) Uiso 1 1 d GR . . . .
H3C H 1.0322 0.2074 0.2994 0.130(6) Uiso 1 1 d GR . . . .
C4 C 0.7200(2) 0.1905(3) 0.32241(10) 0.0499(4) Uani 1 1 d . . . . .
C5 C 0.4237(2) 0.1759(4) 0.29011(16) 0.0814(7) Uani 1 1 d . . . . .
H5A H 0.4277 0.1406 0.2367 0.155(8) Uiso 1 1 d GR . . . .
H5B H 0.3295 0.2661 0.2896 0.155(8) Uiso 1 1 d GR . . . .
H5C H 0.4115 0.0449 0.3179 0.155(8) Uiso 1 1 d GR . . . .
C6 C 0.5606(2) 0.4775(3) 0.36518(12) 0.0609(5) Uani 1 1 d . . . . .
O5 O 0.70954(19) 1.2062(3) 0.52847(11) 0.0868(5) Uani 1 1 d . . . . .
H5D H 0.6451 1.2245 0.5594 0.130 Uiso 1 1 d R . . . .
H5E H 0.8049 1.2478 0.5505 0.130 Uiso 1 1 d R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A H1A 0.8199 . ?
O1A N1A 1.355(3) . ?
O1B H1B 0.8200 . ?
O1B N1B 1.354(3) . ?
O2 C2 1.210(2) . ?
O3 C4 1.205(2) . ?
O4 C6 1.210(2) . ?
N1A C1 1.320(3) . ?
N1B C1 1.318(3) . ?
N2 C2 1.374(2) . ?
N2 C3 1.462(2) . ?
N2 C4 1.389(2) . ?
N3 C4 1.383(2) . ?
N3 C5 1.469(2) . ?
N3 C6 1.371(2) . ?
C1 C2 1.476(3) . ?
C1 C6 1.479(3) . ?
C3 H3A 0.9602 . ?
C3 H3B 0.9602 . ?
C3 H3C 0.9600 . ?
C5 H5A 0.9668 . ?
C5 H5B 0.9673 . ?
C5 H5C 0.9673 . ?
O5 H5D 0.8496 . ?
O5 H5E 0.8499 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1A O1A H1A 110.8 . . ?
N1B O1B H1B 106.9 . . ?
C1 N1A O1A 114.2(3) . . ?
C1 N1B O1B 106.0(3) . . ?
C2 N2 C3 118.84(16) . . ?
C2 N2 C4 124.37(15) . . ?
C4 N2 C3 115.77(16) . . ?
C4 N3 C5 116.57(16) . . ?
C6 N3 C4 125.20(15) . . ?
C6 N3 C5 118.21(15) . . ?
N1A C1 C2 108.12(19) . . ?
N1A C1 C6 131.7(2) . . ?
N1B C1 C2 136.1(2) . . ?
N1B C1 C6 103.7(2) . . ?
C2 C1 C6 120.14(16) . . ?
O2 C2 N2 120.72(18) . . ?
O2 C2 C1 123.61(19) . . ?
N2 C2 C1 115.67(15) . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.4 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.4 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O3 C4 N2 121.02(16) . . ?
O3 C4 N3 121.34(16) . . ?
N3 C4 N2 117.64(16) . . ?
N3 C5 H5A 110.1 . . ?
N3 C5 H5B 110.5 . . ?
N3 C5 H5C 110.0 . . ?
H5A C5 H5B 108.6 . . ?
H5A C5 H5C 108.7 . . ?
H5B C5 H5C 108.9 . . ?
O4 C6 N3 120.73(18) . . ?
O4 C6 C1 123.46(19) . . ?
N3 C6 C1 115.79(15) . . ?
H5D O5 H5E 109.5 . . ?

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
O1A H1A O5 0.82 1.72 2.534(3) 171.1 .
O1B H1B O5 0.82 1.80 2.617(5) 176.7 .
O5 H5D O1A 0.85 2.19 2.807(3) 129.1 3_676
O5 H5D O4 0.85 2.08 2.809(2) 142.9 3_676
O5 H5E O2 0.85 1.93 2.752(2) 163.7 3_776

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
O1A N1A C1 N1B 6.0(6) . . . . ?
O1A N1A C1 C2 -179.0(3) . . . . ?
O1A N1A C1 C6 -0.4(5) . . . . ?
O1B N1B C1 N1A 5.2(5) . . . . ?
O1B N1B C1 C2 -1.8(7) . . . . ?
O1B N1B C1 C6 -179.7(3) . . . . ?
N1A C1 C2 O2 -9.4(3) . . . . ?
N1A C1 C2 N2 169.7(2) . . . . ?
N1A C1 C6 O4 6.0(4) . . . . ?
N1A C1 C6 N3 -175.8(3) . . . . ?
N1B C1 C2 O2 -5.9(5) . . . . ?
N1B C1 C2 N2 173.2(4) . . . . ?
N1B C1 C6 O4 2.9(4) . . . . ?
N1B C1 C6 N3 -178.9(3) . . . . ?
C2 N2 C4 O3 169.68(16) . . . . ?
C2 N2 C4 N3 -11.0(3) . . . . ?
C2 C1 C6 O4 -175.5(2) . . . . ?
C2 C1 C6 N3 2.8(3) . . . . ?
C3 N2 C2 O2 0.6(3) . . . . ?
C3 N2 C2 C1 -178.49(17) . . . . ?
C3 N2 C4 O3 1.3(3) . . . . ?
C3 N2 C4 N3 -179.30(16) . . . . ?
C4 N2 C2 O2 -167.37(18) . . . . ?
C4 N2 C2 C1 13.5(2) . . . . ?
C4 N3 C6 O4 178.4(2) . . . . ?
C4 N3 C6 C1 0.1(3) . . . . ?
C5 N3 C4 O3 1.1(3) . . . . ?
C5 N3 C4 N2 -178.24(17) . . . . ?
C5 N3 C6 O4 0.2(3) . . . . ?
C5 N3 C6 C1 -178.12(18) . . . . ?
C6 N3 C4 O3 -177.14(17) . . . . ?
C6 N3 C4 N2 3.5(3) . . . . ?
C6 C1 C2 O2 171.79(19) . . . . ?
C6 C1 C2 N2 -9.1(2) . . . . ?

_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_symmetry_cell_setting           ?
_symmetry_space_group_name_h-m   ?
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_r10_sq
_database_code_depnum_ccdc_archive 'CCDC 1017332'
_audit_update_record             
;
2014-12-03 deposited with the CCDC.
2015-01-05 downloaded from the CCDC.
;
_audit_creation_date             2014-11-27
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.10.24 svn.r3046 for OlexSys, GUI svn.r3563)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H24 Cd N10 O8'
_chemical_formula_sum            'C26 H28 Cd N10 O10'
_chemical_formula_weight         752.98
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8080 1.2020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           167
_space_group_name_H-M_alt        'R -3 c'
_space_group_name_Hall           '-R 3 2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'y, x, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'y+2/3, x+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'y+1/3, x+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-y, -x, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-y+2/3, -x+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'
'-y+1/3, -x+2/3, z+1/6'

_cell_length_a                   27.5068(12)
_cell_length_b                   27.5068(12)
_cell_length_c                   24.343(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     15950.9(19)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    30542
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.496
_cell_measurement_theta_min      2.392
_shelx_estimated_absorpt_T_max   0.922
_shelx_estimated_absorpt_T_min   0.711
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            pink
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             6876
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.121
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            153107
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.060
_diffrn_reflns_theta_min         2.392
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'ω scans and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3565
_reflns_number_total             5189
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       'Bruker Smart Apex II'
_computing_data_reduction        'Bruker SAINT (1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         5189
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0368
_refine_ls_restrained_S_all      1.113
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0401P)²+22.2317P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.1045
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H3(0.071) H5A(0.132) H5B(0.132) H5C(0.132) H6A(0.128) H6B(0.128)
 H6C(0.128) H8(0.074) H9(0.085) H10(0.089) H11(0.081) H13(0.071)
 Fixed X: H3(0.5646) H5A(0.8334) H5B(0.7781) H5C(0.7753) H6A(0.762)
 H6B(0.8274) H6C(0.7946) H8(0.633301) H9(0.5449) H10(0.4693) H11(0.4788)
 H13(0.661701)
 Fixed Y: Cd1(0.6667) H3(0.5778) H5A(0.527801) H5B(0.4713) H5C(0.5192)
 H6A(0.468201) H6B(0.504499) H6C(0.527801) H8(0.5992) H9(0.567101) H10(0.542)
 H11(0.5461) H13(0.6127)
 Fixed Z: Cd1(0.416699) H3(0.5315) H5A(0.434699) H5B(0.4221) H5C(0.4542)
 H6A(0.222) H6B(0.228101) H6C(0.194901) H8(0.3349) H9(0.2998) H10(0.3566)
 H11(0.451) H13(0.528701)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Cd1 Cd 0.74612(2) 0.6667 0.4167 0.04896(10) Uani 1 2 d S T P . .
O1 O 0.76966(9) 0.59453(9) 0.41960(7) 0.0630(5) Uani 1 1 d . . . . .
O2 O 0.74308(10) 0.65656(10) 0.28468(8) 0.0755(6) Uani 1 1 d . . . . .
O3 O 0.76380(10) 0.58506(9) 0.22593(8) 0.0740(6) Uani 1 1 d . . . . .
O4 O 0.80422(11) 0.47278(10) 0.32729(10) 0.0874(7) Uani 1 1 d . . . . .
N1 N 0.75143(9) 0.63517(10) 0.32710(8) 0.0564(5) Uani 1 1 d . . . . .
N2 N 0.65672(9) 0.60873(10) 0.44733(8) 0.0547(5) Uani 1 1 d . . . . .
N3 N 0.58357(9) 0.58409(10) 0.50176(9) 0.0590(6) Uani 1 1 d . . . . .
H3 H 0.5646 0.5778 0.5315 0.071 Uiso 1 1 d . . . . .
N4 N 0.78829(9) 0.53472(9) 0.37312(8) 0.0559(5) Uani 1 1 d . . . . .
N5 N 0.78608(9) 0.53049(10) 0.27647(9) 0.0578(5) Uani 1 1 d . . . . .
C1 C 0.76516(10) 0.59506(11) 0.32258(10) 0.0496(5) Uani 1 1 d . . . . .
C2 C 0.77411(10) 0.57610(11) 0.37455(10) 0.0523(6) Uani 1 1 d . . . . .
C3 C 0.79333(12) 0.51005(12) 0.32558(12) 0.0612(7) Uani 1 1 d . . . . .
C4 C 0.77087(11) 0.57153(11) 0.27123(10) 0.0543(6) Uani 1 1 d . . . . .
C5 C 0.79438(17) 0.51130(17) 0.42538(13) 0.0879(10) Uani 1 1 d . . . . .
H5A H 0.8334 0.5278 0.4347 0.132 Uiso 1 1 d . . . . .
H5B H 0.7781 0.4713 0.4221 0.132 Uiso 1 1 d . . . . .
H5C H 0.7753 0.5192 0.4542 0.132 Uiso 1 1 d . . . . .
C6 C 0.79324(16) 0.50544(16) 0.22621(13) 0.0848(10) Uani 1 1 d . . . . .
H6A H 0.7620 0.4682 0.2220 0.128 Uiso 1 1 d . . . . .
H6B H 0.8274 0.5045 0.2281 0.128 Uiso 1 1 d . . . . .
H6C H 0.7946 0.5278 0.1949 0.128 Uiso 1 1 d . . . . .
C7 C 0.60912(11) 0.59176(10) 0.41497(10) 0.0488(5) Uani 1 1 d . . . . .
C8 C 0.60271(12) 0.58869(12) 0.35808(11) 0.0610(7) Uani 1 1 d . . . . .
H8 H 0.6333 0.5992 0.3349 0.074 Uiso 1 1 d . . . . .
C9 C 0.55001(14) 0.56990(13) 0.33781(11) 0.0708(8) Uani 1 1 d . . . . .
H9 H 0.5449 0.5671 0.2998 0.085 Uiso 1 1 d . . . . .
C10 C 0.50411(13) 0.55427(14) 0.37224(12) 0.0734(8) Uani 1 1 d . . . . .
H10 H 0.4693 0.5420 0.3566 0.089 Uiso 1 1 d . . . . .
C11 C 0.50958(12) 0.55688(13) 0.42799(12) 0.0677(8) Uani 1 1 d . . . . .
H11 H 0.4788 0.5461 0.4510 0.081 Uiso 1 1 d . . . . .
C12 C 0.56289(11) 0.57631(11) 0.44882(10) 0.0531(6) Uani 1 1 d . . . . .
C13 C 0.63833(11) 0.60353(12) 0.49824(10) 0.0597(7) Uani 1 1 d . . . . .
H13 H 0.6617 0.6127 0.5287 0.071 Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 O1 2.3771(18) . ?
Cd1 O1 2.3761(18) 10_565 ?
Cd1 N1 2.379(2) . ?
Cd1 N1 2.377(2) 10_565 ?
Cd1 N2 2.285(2) 10_565 ?
Cd1 N2 2.286(2) . ?
O1 C2 1.240(3) . ?
O2 N1 1.265(3) . ?
O3 C4 1.210(3) . ?
O4 C3 1.204(3) . ?
N1 C1 1.337(3) . ?
N2 C7 1.393(3) . ?
N2 C13 1.319(3) . ?
N3 C12 1.382(3) . ?
N3 C13 1.325(3) . ?
N4 C2 1.376(3) . ?
N4 C3 1.383(3) . ?
N4 C5 1.473(4) . ?
N5 C3 1.377(3) . ?
N5 C4 1.392(3) . ?
N5 C6 1.465(3) . ?
C1 C2 1.436(3) . ?
C1 C4 1.452(3) . ?
C7 C8 1.393(3) . ?
C7 C12 1.391(4) . ?
C8 C9 1.365(4) . ?
C9 C10 1.392(4) . ?
C10 C11 1.363(4) . ?
C11 C12 1.382(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cd1 O1 92.72(10) 10_565 . ?
O1 Cd1 N1 68.32(7) . . ?
O1 Cd1 N1 68.38(7) 10_565 10_565 ?
O1 Cd1 N1 91.84(7) 10_565 . ?
N1 Cd1 O1 91.87(7) 10_565 . ?
N1 Cd1 N1 151.78(10) 10_565 . ?
N2 Cd1 O1 161.44(6) 10_565 . ?
N2 Cd1 O1 93.15(8) . . ?
N2 Cd1 O1 93.19(8) 10_565 10_565 ?
N2 Cd1 O1 161.54(7) . 10_565 ?
N2 Cd1 N1 93.91(7) 10_565 . ?
N2 Cd1 N1 106.66(7) 10_565 10_565 ?
N2 Cd1 N1 106.59(8) . . ?
N2 Cd1 N1 93.94(7) . 10_565 ?
N2 Cd1 N2 86.72(11) 10_565 . ?
C2 O1 Cd1 116.04(16) . . ?
O2 N1 Cd1 121.35(16) . . ?
O2 N1 C1 120.6(2) . . ?
C1 N1 Cd1 118.05(16) . . ?
C7 N2 Cd1 123.52(16) . . ?
C13 N2 Cd1 127.06(17) . . ?
C13 N2 C7 104.5(2) . . ?
C13 N3 C12 107.4(2) . . ?
C2 N4 C3 124.5(2) . . ?
C2 N4 C5 118.8(2) . . ?
C3 N4 C5 116.5(2) . . ?
C3 N5 C4 125.0(2) . . ?
C3 N5 C6 116.9(2) . . ?
C4 N5 C6 118.1(2) . . ?
N1 C1 C2 113.4(2) . . ?
N1 C1 C4 125.2(2) . . ?
C2 C1 C4 121.4(2) . . ?
O1 C2 N4 119.2(2) . . ?
O1 C2 C1 124.1(2) . . ?
N4 C2 C1 116.7(2) . . ?
O4 C3 N4 121.2(3) . . ?
O4 C3 N5 121.8(3) . . ?
N5 C3 N4 117.1(2) . . ?
O3 C4 N5 119.5(2) . . ?
O3 C4 C1 125.3(2) . . ?
N5 C4 C1 115.2(2) . . ?
C8 C7 N2 130.7(2) . . ?
C12 C7 N2 109.3(2) . . ?
C12 C7 C8 120.1(2) . . ?
C9 C8 C7 117.4(3) . . ?
C8 C9 C10 121.8(3) . . ?
C11 C10 C9 121.6(3) . . ?
C10 C11 C12 117.0(3) . . ?
N3 C12 C7 105.2(2) . . ?
N3 C12 C11 132.6(3) . . ?
C11 C12 C7 122.1(2) . . ?
N2 C13 N3 113.7(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
N3 H3 O2 0.858(2) 2.142(2) 2.839(3) 138.14(15) 9_565
N3 H3 O3 0.858(2) 2.116(2) 2.826(3) 139.84(16) 9_565
C13 H13 O2 0.930(2) 2.2891(19) 3.030(3) 136.29(18) 10_565

_olex2_submission_special_instructions 'No special instructions were received'
_platon_squeeze_details          
;
TITL
CELL   27.5068   27.5068   24.3430     90.00     90.00    120.00
SPGR R-3c
# Solvent Accessible Volume =    3854.1
# Electrons Found in S.A.V. =     262.5
# Note: Atoms in Void as Cxxx and Qxxx all others
C101 1.000 1.003 0.977 !       1.14 eA-3
C102 0.827 1.000 0.251 !       1.10 eA-3
Q103 0.586 1.000 0.250 !       0.81 eA-3
C104 1.000 1.000 0.250 !       0.76 eA-3
C105 1.001 1.003 0.421 !       0.70 eA-3
C106 1.000 1.002 0.875 !       0.63 eA-3
;

####################################################################### 
# 
# 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 1017333'
_audit_update_record             
;
2014-07-31 deposited with the CCDC.
2015-01-05 downloaded from the CCDC.
;
_audit_creation_date             2014-04-17
_audit_creation_method           
;
Olex2 1.2-ac21
(compiled 2014.04.04 svn.r2922, GUI svn.r3563)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C6 H6 N3 O4), C10 H18 Cd N2 O4'
_chemical_formula_sum            'C22 H30 Cd N8 O12'
_chemical_formula_weight         710.94
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4597(5)
_cell_length_b                   9.1787(5)
_cell_length_c                   10.2999(6)
_cell_angle_alpha                88.351(2)
_cell_angle_beta                 85.190(2)
_cell_angle_gamma                62.638(2)
_cell_volume                     707.75(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3341
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.998
_cell_measurement_theta_min      2.499
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.848
_exptl_absorpt_correction_T_max  25.998
_exptl_absorpt_correction_T_min  2.499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            Pink
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             362
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   0.8478
_exptl_transmission_factor_min   0.7008
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12467
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.499
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'ω scans and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2746
_reflns_number_total             2766
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       'Bruker Smart Apex II'
_computing_data_reduction        'Bruker SAINT (2001)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.126
_refine_ls_extinction_coef       0.023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.218
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2766
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0233
_refine_ls_R_factor_gt           0.0231
_refine_ls_restrained_S_all      1.217
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0439P)²+0.0695P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0644
_refine_ls_wR_factor_ref         0.0646
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H2WB-O2W = O2W-H2WA
 0.85 with sigma of 0.02
 H1WA-O1W = O1W-H1WB
 0.85 with sigma of 0.02
 H2WB-H2WA
 1.301 with sigma of 0.04
 H1WA-H1WB
 1.301 with sigma of 0.04
 O2W-H2WB \\sim O2W-H2WA \\sim O1W-H1WA \\sim O1W-H1WB
 with sigma of 0.001
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C7(H7)
3.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 -0.0592(2) 0.4942(2) 0.67036(14) 0.0518(4) Uani 1 1 d . . . . .
O2 O -0.2428(2) 0.3001(3) 0.95267(18) 0.0700(5) Uani 1 1 d . . . . .
O3 O 0.2535(2) 0.1192(3) 1.16977(16) 0.0635(4) Uani 1 1 d . . . . .
O4 O 0.2320(2) 0.4127(2) 0.80391(13) 0.0473(3) Uani 1 1 d . . . . .
N2 N -0.1145(2) 0.4286(2) 0.76294(16) 0.0443(4) Uani 1 1 d . . . . .
N3 N 0.0044(2) 0.2104(2) 1.06202(15) 0.0440(4) Uani 1 1 d . . . . .
N4 N 0.2443(2) 0.2623(2) 0.98426(14) 0.0391(3) Uani 1 1 d . . . . .
C4 C -0.0150(2) 0.3617(2) 0.86225(17) 0.0375(4) Uani 1 1 d . . . . .
C6 C -0.0967(3) 0.2916(3) 0.95904(19) 0.0446(4) Uani 1 1 d . . . . .
C8 C 0.1720(3) 0.1930(2) 1.07804(17) 0.0420(4) Uani 1 1 d . . . . .
C9 C 0.4215(3) 0.2475(3) 1.0023(2) 0.0535(5) Uani 1 1 d . . . . .
H9A H 0.4111 0.3542 1.0186 0.080 Uiso 1 1 calc GR . . . .
H9B H 0.4992 0.2009 0.9250 0.080 Uiso 1 1 calc GR . . . .
H9C H 0.4701 0.1779 1.0750 0.080 Uiso 1 1 calc GR . . . .
C10 C 0.1589(2) 0.3512(2) 0.87768(16) 0.0346(3) Uani 1 1 d . . . . .
C11 C -0.0751(4) 0.1430(4) 1.1640(2) 0.0670(7) Uani 1 1 d . . . . .
H11A H 0.0111 0.0339 1.1845 0.100 Uiso 1 1 calc GR . . . .
H11B H -0.1776 0.1400 1.1334 0.100 Uiso 1 1 calc GR . . . .
H11C H -0.1107 0.2112 1.2407 0.100 Uiso 1 1 calc GR . . . .
Cd1 Cd 0.5000 0.5000 0.5000 0.03384(10) Uani 1 2 d S T P . .
N1 N 0.6017(2) 0.22348(18) 0.46278(14) 0.0376(3) Uani 1 1 d . . . . .
C1 C 0.5374(3) 0.1701(2) 0.37123(17) 0.0407(4) Uani 1 1 d . . . . .
H1 H 0.4441 0.2467 0.3262 0.049 Uiso 1 1 calc R . . . .
C2 C 0.6037(3) 0.0058(2) 0.34060(18) 0.0449(4) Uani 1 1 d . . . . .
H2 H 0.5563 -0.0272 0.2758 0.054 Uiso 1 1 calc R . . . .
C3 C 0.7406(3) -0.1080(2) 0.4074(2) 0.0484(5) Uani 1 1 d . . . . .
H3 H 0.7876 -0.2194 0.3888 0.058 Uiso 1 1 calc R . . . .
C5 C 0.7350(3) 0.1114(2) 0.5273(2) 0.0468(4) Uani 1 1 d . . . . .
H5 H 0.7806 0.1469 0.5916 0.056 Uiso 1 1 calc R . . . .
C7 C 0.8072(3) -0.0542(3) 0.5024(2) 0.0522(5) Uani 1 1 d . . . . .
H7 H 0.8997 -0.1288 0.5492 0.063 Uiso 1 1 calc R . . . .
O1W O 0.21049(19) 0.5461(2) 0.53722(14) 0.0458(3) Uani 1 1 d D . . . .
O2W O 0.5371(2) 0.4554(2) 0.72118(14) 0.0519(4) Uani 1 1 d D . . . .
H1WA H 0.165(3) 0.522(3) 0.6022(14) 0.066(8) Uiso 1 1 d D . . . .
H2WA H 0.461(3) 0.445(4) 0.770(2) 0.088(11) Uiso 1 1 d D . . . .
H2WB H 0.624(2) 0.436(4) 0.763(2) 0.086(11) Uiso 1 1 d D . . . .
H1WB H 0.161(3) 0.531(3) 0.4775(15) 0.052(7) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N2 1.281(2) . ?
O2 C6 1.210(3) . ?
O3 C8 1.212(2) . ?
O4 C10 1.223(2) . ?
N2 C4 1.329(2) . ?
N3 C6 1.390(3) . ?
N3 C8 1.375(3) . ?
N3 C11 1.472(3) . ?
N4 C8 1.391(3) . ?
N4 C9 1.470(3) . ?
N4 C10 1.390(2) . ?
C4 C6 1.463(3) . ?
C4 C10 1.452(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
Cd1 N1 2.3071(15) . y
Cd1 N1 2.3071(15) 2_666 y
Cd1 O1W 2.2856(14) 2_666 y
Cd1 O1W 2.2856(14) . y
Cd1 O2W 2.3247(14) 2_666 y
Cd1 O2W 2.3247(14) . y
N1 C1 1.335(2) . ?
N1 C5 1.338(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.382(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.374(3) . ?
C3 H3 0.9300 . ?
C3 C7 1.376(3) . ?
C5 H5 0.9300 . ?
C5 C7 1.375(3) . ?
C7 H7 0.9300 . ?
O1W H1WA 0.822(8) . ?
O1W H1WB 0.822(8) . ?
O2W H2WA 0.822(8) . ?
O2W H2WB 0.822(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N2 C4 119.67(16) . . ?
C6 N3 C11 118.01(19) . . ?
C8 N3 C6 124.70(16) . . ?
C8 N3 C11 117.26(18) . . ?
C8 N4 C9 117.61(16) . . ?
C10 N4 C8 125.23(15) . . ?
C10 N4 C9 117.10(16) . . ?
N2 C4 C6 112.79(16) . . ?
N2 C4 C10 126.25(17) . . ?
C10 C4 C6 120.95(16) . . ?
O2 C6 N3 120.04(19) . . ?
O2 C6 C4 123.76(19) . . ?
N3 C6 C4 116.19(17) . . ?
O3 C8 N3 121.21(19) . . ?
O3 C8 N4 121.52(19) . . ?
N3 C8 N4 117.27(16) . . ?
N4 C9 H9A 109.5 . . ?
N4 C9 H9B 109.5 . . ?
N4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O4 C10 N4 119.86(16) . . ?
O4 C10 C4 124.58(16) . . ?
N4 C10 C4 115.55(16) . . ?
N3 C11 H11A 109.5 . . ?
N3 C11 H11B 109.5 . . ?
N3 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 Cd1 N1 180.0 2_666 . y
N1 Cd1 O2W 91.07(6) . . y
N1 Cd1 O2W 88.93(6) . 2_666 y
N1 Cd1 O2W 91.07(6) 2_666 2_666 y
N1 Cd1 O2W 88.93(6) 2_666 . y
O1W Cd1 N1 87.51(6) . 2_666 y
O1W Cd1 N1 92.49(6) 2_666 2_666 y
O1W Cd1 N1 87.51(6) 2_666 . y
O1W Cd1 N1 92.49(6) . . y
O1W Cd1 O1W 180.0 . 2_666 y
O1W Cd1 O2W 90.20(5) . 2_666 y
O1W Cd1 O2W 89.80(5) . . y
O1W Cd1 O2W 90.20(5) 2_666 . y
O1W Cd1 O2W 89.80(5) 2_666 2_666 y
O2W Cd1 O2W 180.0 2_666 . y
C1 N1 Cd1 121.33(12) . . ?
C1 N1 C5 117.79(16) . . ?
C5 N1 Cd1 120.76(13) . . ?
N1 C1 H1 118.6 . . ?
N1 C1 C2 122.74(18) . . ?
C2 C1 H1 118.6 . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.88(18) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 120.6 . . ?
C2 C3 C7 118.79(18) . . ?
C7 C3 H3 120.6 . . ?
N1 C5 H5 118.7 . . ?
N1 C5 C7 122.69(19) . . ?
C7 C5 H5 118.7 . . ?
C3 C7 H7 120.4 . . ?
C5 C7 C3 119.10(19) . . ?
C5 C7 H7 120.4 . . ?
Cd1 O1W H1WA 127.5(18) . . ?
Cd1 O1W H1WB 119.1(15) . . ?
H1WA O1W H1WB 103(2) . . ?
Cd1 O2W H2WA 121(2) . . ?
Cd1 O2W H2WB 130.7(19) . . ?
H2WA O2W H2WB 108(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
O1W H1WA O1 0.822(8) 2.086(17) 2.784(2) 143(2) .
O1W H1WA O4 0.822(8) 2.280(16) 2.9602(19) 140(2) .
O2W H2WA O4 0.822(8) 2.094(15) 2.843(2) 151(3) .
O2W H2WB O2 0.822(8) 2.37(2) 3.048(2) 141(3) 1_655
O2W H2WB N2 0.822(8) 2.186(16) 2.910(2) 147(3) 1_655
O1W H1WB O1 0.822(8) 1.880(8) 2.699(2) 174(2) 2_566

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
O1 N2 C4 C6 -179.70(18) . . . . ?
O1 N2 C4 C10 -1.3(3) . . . . ?
N2 C4 C6 O2 -3.2(3) . . . . ?
N2 C4 C6 N3 176.19(18) . . . . ?
N2 C4 C10 O4 4.9(3) . . . . ?
N2 C4 C10 N4 -174.37(18) . . . . ?
C6 N3 C8 O3 -179.3(2) . . . . ?
C6 N3 C8 N4 0.2(3) . . . . ?
C6 C4 C10 O4 -176.77(19) . . . . ?
C6 C4 C10 N4 3.9(2) . . . . ?
C8 N3 C6 O2 179.6(2) . . . . ?
C8 N3 C6 C4 0.2(3) . . . . ?
C8 N4 C10 O4 176.95(18) . . . . ?
C8 N4 C10 C4 -3.7(3) . . . . ?
C9 N4 C8 O3 -1.9(3) . . . . ?
C9 N4 C8 N3 178.59(19) . . . . ?
C9 N4 C10 O4 0.1(3) . . . . ?
C9 N4 C10 C4 179.41(17) . . . . ?
C10 N4 C8 O3 -178.7(2) . . . . ?
C10 N4 C8 N3 1.7(3) . . . . ?
C10 C4 C6 O2 178.3(2) . . . . ?
C10 C4 C6 N3 -2.3(3) . . . . ?
C11 N3 C6 O2 -2.7(3) . . . . ?
C11 N3 C6 C4 177.9(2) . . . . ?
C11 N3 C8 O3 2.9(3) . . . . ?
C11 N3 C8 N4 -177.6(2) . . . . ?
Cd1 N1 C1 C2 175.57(14) . . . . ?
Cd1 N1 C5 C7 -175.84(17) . . . . ?
N1 C1 C2 C3 0.4(3) . . . . ?
N1 C5 C7 C3 0.1(4) . . . . ?
C1 N1 C5 C7 0.3(3) . . . . ?
C1 C2 C3 C7 -0.1(3) . . . . ?
C2 C3 C7 C5 -0.1(3) . . . . ?
C5 N1 C1 C2 -0.5(3) . . . . ?


