# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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 1519899'








_audit_update_record             
;
2017-08-21 deposited with the CCDC.
2017-09-08 downloaded from the CCDC.
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
Compound_1
;

_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H13 Cd2 N5 O5'
_chemical_formula_weight         628.15

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                   28.5633(17)
_cell_length_b                   10.0564(6)
_cell_length_c                   18.6924(11)
_cell_angle_alpha                90
_cell_angle_beta                 129.554(2)
_cell_angle_gamma                90
_cell_volume                     4139.8(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    474
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      26.15

_exptl_crystal_description       plate
_exptl_crystal_colour            bronze
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.016
_exptl_crystal_F_000             2432
_exptl_transmission_factor_min   0.6607
_exptl_transmission_factor_max   0.7455
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    2.098
_shelx_estimated_absorpt_T_min   0.884
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADBAS

_exptl_special_details           ?

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19932
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.849
_diffrn_reflns_theta_max         27.182
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4581
_reflns_number_gt                3429
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0235P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4581
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0634
_refine_ls_wR_factor_gt          0.0563
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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
Cd1 Cd 0.08609(2) 0.90228(3) 0.33196(2) 0.02060(8) Uani 1 1 d . . . . .
Cd2 Cd 0.00448(2) 0.98706(3) 0.09793(2) 0.01941(8) Uani 1 1 d . . . . .
O1 O -0.06757(11) 0.7857(3) 0.01665(17) 0.0245(6) Uani 1 1 d . . . . .
O2 O 0.01672(11) 0.8167(3) 0.19069(16) 0.0212(6) Uani 1 1 d . . . . .
O3 O 0.16943(13) 1.2067(3) 0.2935(2) 0.0494(10) Uani 1 1 d . . . . .
O4 O 0.09607(17) 1.2787(3) 0.3796(3) 0.0613(11) Uani 1 1 d . . . . .
O5 O -0.13034(16) 1.2480(4) -0.1114(2) 0.0736(13) Uani 1 1 d . . . . .
N1 N 0.11604(13) 0.6876(3) 0.3714(2) 0.0198(7) Uani 1 1 d . . . . .
N2 N 0.18235(14) 0.9034(3) 0.4775(2) 0.0262(8) Uani 1 1 d . . . . .
N3 N 0.09378(14) 1.0444(3) 0.2410(2) 0.0224(8) Uani 1 1 d . . . . .
N4 N -0.04570(14) 1.1054(3) -0.0375(2) 0.0233(8) Uani 1 1 d . . . . .
N5 N 0.05550(14) 1.0700(3) 0.3736(2) 0.0239(8) Uani 1 1 d . . . . .
C1 C -0.10907(18) 0.7756(4) -0.0826(3) 0.0289(10) Uani 1 1 d . . . . .
H1A H -0.0875 0.7425 -0.1039 0.035 Uiso 1 1 calc R U . . .
H1B H -0.1262 0.8635 -0.1097 0.035 Uiso 1 1 calc R U . . .
H1C H -0.1419 0.7140 -0.1022 0.035 Uiso 1 1 calc R U . . .
C2 C -0.03567(16) 0.6711(4) 0.0650(3) 0.0208(9) Uani 1 1 d . . . . .
C3 C -0.04700(17) 0.5469(4) 0.0262(3) 0.0268(10) Uani 1 1 d . . . . .
H3 H -0.0785 0.5346 -0.0385 0.032 Uiso 1 1 calc R U . . .
C4 C -0.01200(18) 0.4395(4) 0.0825(3) 0.0304(10) Uani 1 1 d . . . . .
H4 H -0.0196 0.3534 0.0561 0.036 Uiso 1 1 calc R U . . .
C5 C 0.03331(18) 0.4571(4) 0.1757(3) 0.0279(10) Uani 1 1 d . . . . .
H5 H 0.0567 0.3828 0.2134 0.033 Uiso 1 1 calc R U . . .
C6 C 0.04590(16) 0.5834(4) 0.2167(3) 0.0200(9) Uani 1 1 d . . . . .
C7 C 0.01052(16) 0.6937(4) 0.1609(3) 0.0207(9) Uani 1 1 d . . . . .
C8 C 0.09596(16) 0.5870(4) 0.3157(3) 0.0220(9) Uani 1 1 d . . . . .
H8 H 0.1166 0.5053 0.3433 0.026 Uiso 1 1 calc R U . . .
C9 C 0.16566(16) 0.6670(4) 0.4675(3) 0.0226(9) Uani 1 1 d . . . . .
C10 C 0.17969(17) 0.5468(4) 0.5125(3) 0.0287(10) Uani 1 1 d . . . . .
H10 H 0.1562 0.4705 0.4781 0.034 Uiso 1 1 calc R U . . .
C11 C 0.22775(19) 0.5348(5) 0.6075(3) 0.0397(12) Uani 1 1 d . . . . .
H11 H 0.2366 0.4507 0.6367 0.048 Uiso 1 1 calc R U . . .
C12 C 0.26222(19) 0.6424(5) 0.6591(3) 0.0387(12) Uani 1 1 d . . . . .
H12 H 0.2956 0.6323 0.7233 0.046 Uiso 1 1 calc R U . . .
C13 C 0.24824(17) 0.7690(4) 0.6168(3) 0.0288(10) Uani 1 1 d . . . . .
C14 C 0.19917(16) 0.7818(4) 0.5207(3) 0.0245(10) Uani 1 1 d . . . . .
C15 C 0.27963(18) 0.8866(5) 0.6669(3) 0.0396(12) Uani 1 1 d . . . . .
H15 H 0.3127 0.8820 0.7316 0.048 Uiso 1 1 calc R U . . .
C16 C 0.26258(19) 1.0059(5) 0.6226(3) 0.0412(12) Uani 1 1 d . . . . .
H16 H 0.2836 1.0851 0.6554 0.049 Uiso 1 1 calc R U . . .
C17 C 0.21296(18) 1.0090(5) 0.5269(3) 0.0359(11) Uani 1 1 d . . . . .
H17 H 0.2010 1.0926 0.4962 0.043 Uiso 1 1 calc R U . . .
C18 C 0.13048(18) 1.1242(5) 0.2667(3) 0.0278(10) Uani 1 1 d . . . . .
C19 C -0.0877(2) 1.1745(5) -0.0746(3) 0.0317(11) Uani 1 1 d . . . . .
C20 C 0.0749(2) 1.1745(5) 0.3761(3) 0.0322(11) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 O2 2.231(2) . ?
Cd1 N5 2.253(3) . ?
Cd1 N1 2.266(3) . ?
Cd1 N2 2.331(3) . ?
Cd1 N3 2.336(3) . ?
Cd2 N5 2.253(3) 2 ?
Cd2 N4 2.285(3) 5_575 ?
Cd2 N4 2.292(3) . ?
Cd2 O2 2.300(3) . ?
Cd2 N3 2.303(3) . ?
Cd2 O1 2.581(3) . ?
O1 C2 1.388(4) . ?
O1 C1 1.434(4) . ?
O2 C7 1.322(4) . ?
O3 C18 1.211(5) . ?
O4 C20 1.191(5) . ?
O5 C19 1.198(5) . ?
N1 C8 1.293(5) . ?
N1 C9 1.428(5) . ?
N2 C17 1.310(5) . ?
N2 C14 1.373(5) . ?
N3 C18 1.154(5) . ?
N4 C19 1.160(5) . ?
N4 Cd2 2.285(3) 5_575 ?
N5 C20 1.175(5) . ?
N5 Cd2 2.253(3) 2 ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.375(5) . ?
C2 C7 1.412(5) . ?
C3 C4 1.391(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.368(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.406(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.413(5) . ?
C6 C8 1.450(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.378(5) . ?
C9 C14 1.422(5) . ?
C10 C11 1.396(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.363(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.416(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.415(5) . ?
C13 C15 1.417(6) . ?
C15 C16 1.359(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.408(6) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cd1 N5 116.74(10) . . ?
O2 Cd1 N1 83.34(10) . . ?
N5 Cd1 N1 138.61(12) . . ?
O2 Cd1 N2 151.88(11) . . ?
N5 Cd1 N2 91.25(12) . . ?
N1 Cd1 N2 72.84(11) . . ?
O2 Cd1 N3 78.39(10) . . ?
N5 Cd1 N3 91.73(12) . . ?
N1 Cd1 N3 128.93(11) . . ?
N2 Cd1 N3 105.00(11) . . ?
N5 Cd2 N4 167.50(12) 2 5_575 ?
N5 Cd2 N4 91.95(11) 2 . ?
N4 Cd2 N4 79.74(13) 5_575 . ?
N5 Cd2 O2 82.57(10) 2 . ?
N4 Cd2 O2 101.01(10) 5_575 . ?
N4 Cd2 O2 155.07(10) . . ?
N5 Cd2 N3 94.55(11) 2 . ?
N4 Cd2 N3 97.92(11) 5_575 . ?
N4 Cd2 N3 127.14(11) . . ?
O2 Cd2 N3 77.68(10) . . ?
N5 Cd2 O1 89.33(10) 2 . ?
N4 Cd2 O1 81.87(10) 5_575 . ?
N4 Cd2 O1 93.09(10) . . ?
O2 Cd2 O1 62.67(8) . . ?
N3 Cd2 O1 139.30(10) . . ?
C2 O1 C1 116.3(3) . . ?
C2 O1 Cd2 108.7(2) . . ?
C1 O1 Cd2 120.6(2) . . ?
C7 O2 Cd1 129.8(2) . . ?
C7 O2 Cd2 117.7(2) . . ?
Cd1 O2 Cd2 101.49(10) . . ?
C8 N1 C9 118.4(3) . . ?
C8 N1 Cd1 127.0(3) . . ?
C9 N1 Cd1 114.4(2) . . ?
C17 N2 C14 118.8(4) . . ?
C17 N2 Cd1 126.0(3) . . ?
C14 N2 Cd1 113.1(2) . . ?
C18 N3 Cd2 134.2(3) . . ?
C18 N3 Cd1 127.2(3) . . ?
Cd2 N3 Cd1 98.29(12) . . ?
C19 N4 Cd2 127.6(3) . 5_575 ?
C19 N4 Cd2 130.8(3) . . ?
Cd2 N4 Cd2 100.26(13) 5_575 . ?
C20 N5 Cd2 137.0(3) . 2 ?
C20 N5 Cd1 114.0(3) . . ?
Cd2 N5 Cd1 108.96(14) 2 . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 O1 125.0(3) . . ?
C3 C2 C7 122.1(4) . . ?
O1 C2 C7 112.8(3) . . ?
C2 C3 C4 119.5(4) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 120.3(4) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 121.2(4) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C7 119.5(4) . . ?
C5 C6 C8 114.9(4) . . ?
C7 C6 C8 125.6(4) . . ?
O2 C7 C2 116.9(4) . . ?
O2 C7 C6 125.7(3) . . ?
C2 C7 C6 117.5(4) . . ?
N1 C8 C6 128.2(4) . . ?
N1 C8 H8 115.9 . . ?
C6 C8 H8 115.9 . . ?
C10 C9 C14 118.8(4) . . ?
C10 C9 N1 124.4(4) . . ?
C14 C9 N1 116.7(4) . . ?
C9 C10 C11 121.3(4) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C12 C11 C10 120.9(4) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 119.9(4) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 119.3(4) . . ?
C14 C13 C15 117.5(4) . . ?
C12 C13 C15 123.1(4) . . ?
N2 C14 C13 121.3(4) . . ?
N2 C14 C9 119.0(4) . . ?
C13 C14 C9 119.7(4) . . ?
C16 C15 C13 120.2(4) . . ?
C16 C15 H15 119.9 . . ?
C13 C15 H15 119.9 . . ?
C15 C16 C17 118.3(4) . . ?
C15 C16 H16 120.8 . . ?
C17 C16 H16 120.8 . . ?
N2 C17 C16 123.9(4) . . ?
N2 C17 H17 118.1 . . ?
C16 C17 H17 118.1 . . ?
N3 C18 O3 179.2(5) . . ?
N4 C19 O5 178.6(5) . . ?
N5 C20 O4 178.2(5) . . ?

_refine_diff_density_max         0.864
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.129

_shelxl_version_number           2013-4




_publcif_funding_html            
;
;
