# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_TA_C
_database_code_depnum_ccdc_archive 'CCDC 1526721'
_audit_update_record             
;
2017-01-11 deposited with the CCDC.
2017-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 Cd N4 O11'
_chemical_formula_weight         652.84

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd 0.1185 4.6533 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   15.6931(4)
_cell_length_b                   10.3418(3)
_cell_length_c                   15.1640(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2461.04(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9802
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      68.22

_exptl_crystal_description       bulk
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_F_000             1312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.32
_exptl_absorpt_coefficient_mu    7.754
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4424
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26716
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.275
_diffrn_reflns_theta_max         68.244
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4473
_reflns_number_gt                4353
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.919
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0562P)²+6.3355P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4473
_refine_ls_number_parameters     379
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.1057
_refine_ls_wR_factor_gt          0.1048
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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 -0.02746(3) 1.26964(4) 0.35884(6) 0.02738(17) Uani 1 1 d . . . . .
O1 O -0.0329(4) 1.0830(6) 0.2671(5) 0.0365(18) Uani 1 1 d . . . . .
O2 O 0.0891(4) 1.1233(5) 0.3351(4) 0.0351(14) Uani 1 1 d . . . . .
O3 O 0.5538(5) -0.5397(7) -0.0507(5) 0.0467(19) Uani 1 1 d . . . . .
O4 O 0.4233(4) -0.6061(5) -0.0677(4) 0.0356(14) Uani 1 1 d . . . . .
O5 O -0.0064(5) 1.4257(6) 0.2438(5) 0.0382(15) Uani 1 1 d . . . . .
O6 O -0.1359(4) 1.3693(7) 0.2634(5) 0.0453(16) Uani 1 1 d . . . . .
O7 O -0.1090(5) 1.5302(8) 0.1768(5) 0.0552(19) Uani 1 1 d . . . . .
O8 O -0.1567(5) 1.1816(11) 0.4198(7) 0.075(3) Uani 1 1 d . . . . .
O9 O -0.0427(6) 1.1128(11) 0.4805(6) 0.056(2) Uani 1 1 d . . . . .
O10 O -0.1623(7) 1.0265(10) 0.5158(9) 0.095(4) Uani 1 1 d . . . . .
O11 O 0.6158(11) -0.2292(19) -0.1459(19) 0.044(4) Uani 0.3333 1 d . . P . .
O12 O 0.6664(11) -0.332(2) -0.1049(10) 0.035(4) Uani 0.3333 1 d . . P . .
O13 O 0.6773(14) -0.2136(18) -0.0923(13) 0.042(5) Uani 0.3333 1 d . . P . .
C1 C 0.0410(5) 1.0533(8) 0.2908(6) 0.0288(17) Uani 1 1 d . . . . .
C2 C 0.0725(5) 0.9184(7) 0.2652(6) 0.0273(16) Uani 1 1 d . . . . .
C3 C 0.0329(6) 0.8482(10) 0.1988(7) 0.033(2) Uani 1 1 d . . . . .
H3A H -0.0140 0.8847 0.1681 0.040 Uiso 1 1 calc R U . . .
C4 C 0.0612(6) 0.7252(8) 0.1767(7) 0.0334(19) Uani 1 1 d . . . . .
H4A H 0.0335 0.6765 0.1320 0.040 Uiso 1 1 calc R U . . .
C5 C 0.1305(5) 0.6754(8) 0.2211(6) 0.0278(18) Uani 1 1 d . . . . .
C6 C 0.1702(5) 0.7425(7) 0.2883(6) 0.0278(17) Uani 1 1 d . . . . .
H6A H 0.2168 0.7052 0.3189 0.033 Uiso 1 1 calc R U . . .
C7 C 0.1413(5) 0.8645(7) 0.3104(5) 0.0270(17) Uani 1 1 d . . . . .
H7A H 0.1684 0.9116 0.3563 0.032 Uiso 1 1 calc R U . . .
C8 C 0.1729(6) 0.5161(8) 0.1138(6) 0.0301(17) Uani 1 1 d . . . . .
H8A H 0.1575 0.5757 0.0688 0.036 Uiso 1 1 calc R U . . .
C9 C 0.2073(5) 0.3976(7) 0.0914(6) 0.0303(17) Uani 1 1 d . . . . .
H9A H 0.2159 0.3762 0.0311 0.036 Uiso 1 1 calc R U . . .
C10 C 0.2295(5) 0.3098(8) 0.1567(5) 0.0276(17) Uani 1 1 d . . . . .
C11 C 0.2112(6) 0.3408(8) 0.2441(6) 0.0339(19) Uani 1 1 d . . . . .
H11A H 0.2211 0.2797 0.2897 0.041 Uiso 1 1 calc R U . . .
C12 C 0.1785(5) 0.4618(8) 0.2636(6) 0.0323(18) Uani 1 1 d . . . . .
H12A H 0.1679 0.4849 0.3233 0.039 Uiso 1 1 calc R U . . .
C13 C 0.2710(5) 0.1867(8) 0.1332(5) 0.0267(16) Uani 1 1 d . . . . .
C14 C 0.2633(6) 0.0770(8) 0.1857(6) 0.0339(19) Uani 1 1 d . . . . .
H14A H 0.2311 0.0808 0.2386 0.041 Uiso 1 1 calc R U . . .
C15 C 0.3019(6) -0.0371(8) 0.1615(6) 0.0345(19) Uani 1 1 d . . . . .
H15A H 0.2960 -0.1119 0.1973 0.041 Uiso 1 1 calc R U . . .
C16 C 0.3591(5) 0.0634(8) 0.0360(5) 0.0297(17) Uani 1 1 d . . . . .
H16A H 0.3927 0.0569 -0.0160 0.036 Uiso 1 1 calc R U . . .
C17 C 0.3231(5) 0.1779(8) 0.0579(6) 0.0287(17) Uani 1 1 d . . . . .
H17A H 0.3329 0.2522 0.0225 0.034 Uiso 1 1 calc R U . . .
C18 C 0.3823(5) -0.1654(7) 0.0589(5) 0.0276(16) Uani 1 1 d . . . . .
C19 C 0.4678(6) -0.1880(11) 0.0550(8) 0.041(3) Uani 1 1 d . . . . .
H19A H 0.5069 -0.1233 0.0735 0.049 Uiso 1 1 calc R U . . .
C20 C 0.4967(7) -0.3029(10) 0.0246(7) 0.043(2) Uani 1 1 d . . . . .
H20A H 0.5564 -0.3178 0.0228 0.052 Uiso 1 1 calc R U . . .
C21 C 0.4424(6) -0.3989(9) -0.0038(6) 0.0319(18) Uani 1 1 d . . . . .
C22 C 0.3567(6) -0.3781(8) 0.0025(6) 0.033(2) Uani 1 1 d . . . . .
H22A H 0.3181 -0.4439 -0.0153 0.040 Uiso 1 1 calc R U . . .
C23 C 0.3250(6) -0.2599(7) 0.0353(7) 0.035(2) Uani 1 1 d . . . . .
H23A H 0.2654 -0.2458 0.0408 0.042 Uiso 1 1 calc R U . . .
C24 C 0.4752(6) -0.5219(8) -0.0426(6) 0.031(2) Uani 1 1 d . . . . .
N1 N 0.1614(4) 0.5474(7) 0.1985(5) 0.0267(14) Uani 1 1 d . . . . .
N2 N 0.3477(4) -0.0422(6) 0.0876(5) 0.0269(14) Uani 1 1 d . . . . .
N3 N -0.0852(5) 1.4420(7) 0.2279(5) 0.0346(17) Uani 1 1 d . . . . .
N4 N -0.1205(5) 1.1085(7) 0.4718(5) 0.0356(17) 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 O4 2.359(6) 4_575 ?
Cd1 O1 2.381(7) . ?
Cd1 O5 2.399(7) . ?
Cd1 O2 2.400(6) . ?
Cd1 O8 2.408(9) . ?
Cd1 O3 2.437(7) 4_575 ?
Cd1 O6 2.460(7) . ?
Cd1 O9 2.468(9) . ?
Cd1 C1 2.688(8) . ?
Cd1 C24 2.748(8) 4_575 ?
O1 C1 1.252(10) . ?
O2 C1 1.244(10) . ?
O3 C24 1.253(12) . ?
O3 Cd1 2.437(7) 4_534 ?
O4 C24 1.252(11) . ?
O4 Cd1 2.359(6) 4_534 ?
O5 N3 1.272(10) . ?
O6 N3 1.219(11) . ?
O7 N3 1.253(11) . ?
O8 N4 1.231(12) . ?
O9 N4 1.228(11) . ?
O10 N4 1.263(11) . ?
O11 O13 1.27(3) . ?
O11 O12 1.46(3) . ?
O12 O13 1.25(3) . ?
C1 C2 1.530(10) . ?
C2 C3 1.388(13) . ?
C2 C7 1.396(12) . ?
C3 C4 1.389(13) . ?
C4 C5 1.378(13) . ?
C5 C6 1.380(13) . ?
C5 N1 1.452(10) . ?
C6 C7 1.382(11) . ?
C8 N1 1.337(11) . ?
C8 C9 1.382(12) . ?
C9 C10 1.388(12) . ?
C10 C11 1.394(12) . ?
C10 C13 1.475(11) . ?
C11 C12 1.385(12) . ?
C12 N1 1.354(11) . ?
C13 C14 1.391(11) . ?
C13 C17 1.406(12) . ?
C14 C15 1.376(12) . ?
C15 N2 1.331(11) . ?
C16 N2 1.356(11) . ?
C16 C17 1.355(12) . ?
C18 C19 1.362(12) . ?
C18 C23 1.376(12) . ?
C18 N2 1.452(9) . ?
C19 C20 1.353(14) . ?
C20 C21 1.378(14) . ?
C21 C22 1.365(13) . ?
C21 C24 1.494(12) . ?
C22 C23 1.410(12) . ?
C24 Cd1 2.748(8) 4_534 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Cd1 O1 137.9(2) 4_575 . ?
O4 Cd1 O5 83.2(2) 4_575 . ?
O1 Cd1 O5 97.2(3) . . ?
O4 Cd1 O2 83.5(2) 4_575 . ?
O1 Cd1 O2 55.2(2) . . ?
O5 Cd1 O2 102.1(2) . . ?
O4 Cd1 O8 127.5(3) 4_575 . ?
O1 Cd1 O8 83.5(3) . . ?
O5 Cd1 O8 130.5(3) . . ?
O2 Cd1 O8 117.4(3) . . ?
O4 Cd1 O3 53.9(2) 4_575 4_575 ?
O1 Cd1 O3 168.1(2) . 4_575 ?
O5 Cd1 O3 83.6(3) . 4_575 ?
O2 Cd1 O3 136.3(2) . 4_575 ?
O8 Cd1 O3 87.0(3) . 4_575 ?
O4 Cd1 O6 121.9(2) 4_575 . ?
O1 Cd1 O6 88.3(2) . . ?
O5 Cd1 O6 52.1(2) . . ?
O2 Cd1 O6 134.6(2) . . ?
O8 Cd1 O6 78.6(3) . . ?
O3 Cd1 O6 82.8(3) 4_575 . ?
O4 Cd1 O9 94.2(3) 4_575 . ?
O1 Cd1 O9 84.3(3) . . ?
O5 Cd1 O9 177.2(3) . . ?
O2 Cd1 O9 76.8(3) . . ?
O8 Cd1 O9 51.9(3) . . ?
O3 Cd1 O9 95.4(3) 4_575 . ?
O6 Cd1 O9 130.4(3) . . ?
O4 Cd1 C1 111.0(2) 4_575 . ?
O1 Cd1 C1 27.8(2) . . ?
O5 Cd1 C1 103.0(2) . . ?
O2 Cd1 C1 27.6(2) . . ?
O8 Cd1 C1 99.7(3) . . ?
O3 Cd1 C1 163.2(3) 4_575 . ?
O6 Cd1 C1 113.5(3) . . ?
O9 Cd1 C1 77.2(3) . . ?
O4 Cd1 C24 27.0(3) 4_575 4_575 ?
O1 Cd1 C24 164.7(3) . 4_575 ?
O5 Cd1 C24 80.0(3) . 4_575 ?
O2 Cd1 C24 110.4(2) . 4_575 ?
O8 Cd1 C24 109.8(3) . 4_575 ?
O3 Cd1 C24 27.1(3) 4_575 4_575 ?
O6 Cd1 C24 101.4(3) . 4_575 ?
O9 Cd1 C24 97.9(3) . 4_575 ?
C1 Cd1 C24 138.0(3) . 4_575 ?
C1 O1 Cd1 89.9(5) . . ?
C1 O2 Cd1 89.2(5) . . ?
C24 O3 Cd1 90.4(6) . 4_534 ?
C24 O4 Cd1 94.1(5) . 4_534 ?
N3 O5 Cd1 95.3(6) . . ?
N3 O6 Cd1 93.8(5) . . ?
N4 O8 Cd1 95.1(6) . . ?
N4 O9 Cd1 92.3(6) . . ?
O13 O11 O12 53.8(14) . . ?
O13 O12 O11 55.2(15) . . ?
O12 O13 O11 71.0(16) . . ?
O2 C1 O1 125.1(8) . . ?
O2 C1 C2 118.2(7) . . ?
O1 C1 C2 116.7(8) . . ?
O2 C1 Cd1 63.3(4) . . ?
O1 C1 Cd1 62.4(5) . . ?
C2 C1 Cd1 170.2(6) . . ?
C3 C2 C7 119.5(7) . . ?
C3 C2 C1 121.1(8) . . ?
C7 C2 C1 119.3(7) . . ?
C2 C3 C4 120.8(8) . . ?
C5 C4 C3 118.4(8) . . ?
C4 C5 C6 121.9(8) . . ?
C4 C5 N1 119.2(8) . . ?
C6 C5 N1 118.9(7) . . ?
C5 C6 C7 119.4(8) . . ?
C6 C7 C2 119.9(8) . . ?
N1 C8 C9 120.3(8) . . ?
C8 C9 C10 120.2(8) . . ?
C9 C10 C11 118.5(7) . . ?
C9 C10 C13 120.2(7) . . ?
C11 C10 C13 121.3(7) . . ?
C12 C11 C10 119.2(8) . . ?
N1 C12 C11 120.6(8) . . ?
C14 C13 C17 117.6(7) . . ?
C14 C13 C10 121.8(7) . . ?
C17 C13 C10 120.6(7) . . ?
C15 C14 C13 120.5(8) . . ?
N2 C15 C14 119.7(8) . . ?
N2 C16 C17 120.5(7) . . ?
C16 C17 C13 119.9(8) . . ?
C19 C18 C23 120.7(8) . . ?
C19 C18 N2 122.2(8) . . ?
C23 C18 N2 117.1(7) . . ?
C20 C19 C18 119.7(10) . . ?
C19 C20 C21 122.2(10) . . ?
C22 C21 C20 118.3(9) . . ?
C22 C21 C24 120.1(8) . . ?
C20 C21 C24 121.6(8) . . ?
C21 C22 C23 120.6(9) . . ?
C18 C23 C22 118.5(8) . . ?
O3 C24 O4 120.6(8) . . ?
O3 C24 C21 120.2(8) . . ?
O4 C24 C21 119.1(8) . . ?
O3 C24 Cd1 62.5(5) . 4_534 ?
O4 C24 Cd1 58.9(4) . 4_534 ?
C21 C24 Cd1 170.2(6) . 4_534 ?
C8 N1 C12 121.1(7) . . ?
C8 N1 C5 119.6(7) . . ?
C12 N1 C5 119.3(7) . . ?
C15 N2 C16 121.7(7) . . ?
C15 N2 C18 119.3(7) . . ?
C16 N2 C18 118.9(7) . . ?
O6 N3 O7 121.8(8) . . ?
O6 N3 O5 118.0(8) . . ?
O7 N3 O5 120.2(8) . . ?
O8 N4 O9 120.3(9) . . ?
O8 N4 O10 120.7(10) . . ?
O9 N4 O10 118.9(10) . . ?

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
C6 H6A O6 0.95 2.58 3.278(11) 130.8 3_575
C8 H8A O3 0.95 2.46 3.127(11) 126.8 3_455
C12 H12A O4 0.95 2.38 3.095(11) 131.8 4_565
C16 H16A O2 0.95 2.38 3.212(10) 146.5 4_544
C17 H17A O4 0.95 2.46 3.330(10) 153.0 1_565
C23 H23A O8 0.95 2.59 3.270(13) 128.6 2_564

_refine_diff_density_max         0.890
_refine_diff_density_min         -1.026
_refine_diff_density_rms         0.098

_shelxl_version_number           2014-3

