# 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 2018

####################################################################### 
# 
# 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_xszao
_database_code_depnum_ccdc_archive 'CCDC 1550202'
_audit_update_record             
;
2017-08-03 deposited with the CCDC.
2018-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H20 Cd N4 O9'
_chemical_formula_weight         644.86

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P2(1)2(1)2(1) '

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

_cell_length_a                   8.3252(4)
_cell_length_b                   9.3565(5)
_cell_length_c                   32.4860(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2530.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6677
_cell_measurement_theta_min      3.0802
_cell_measurement_theta_max      29.3925

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.693
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1296
_exptl_absorpt_coefficient_mu    0.927
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16224
_diffrn_reflns_av_R_equivalents  0.0781
_diffrn_reflns_av_sigmaI/netI    0.0698
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         25.35
_reflns_number_total             4611
_reflns_number_gt                4234
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0528P)²+1.8665P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.55(3)
_refine_ls_number_reflns         4611
_refine_ls_number_parameters     367
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1120
_refine_ls_wR_factor_gt          0.1083
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 1.07493(5) 0.30795(5) 0.180619(12) 0.01635(13) Uani 1 1 d . . .
O4 O 1.2287(5) 0.1924(6) -0.01785(12) 0.0307(10) Uani 1 1 d . . .
O1 O 0.9024(5) 0.1781(4) 0.13866(11) 0.0207(9) Uani 1 1 d . . .
O2 O 0.8814(5) 0.0784(5) 0.07673(12) 0.0218(10) Uani 1 1 d . . .
O3 O 1.0154(5) 0.0876(5) 0.00922(13) 0.0241(10) Uani 1 1 d . . .
H3 H 0.9599 0.0976 0.0299 0.036 Uiso 1 1 calc R . .
C6 C 1.3862(8) 0.5138(6) 0.10895(19) 0.0185(14) Uani 1 1 d . . .
C1 C 0.9437(7) 0.1661(6) 0.10100(17) 0.0174(13) Uani 1 1 d . . .
C8 C 1.4579(8) 0.6965(7) 0.15760(18) 0.0249(14) Uani 1 1 d . . .
H8 H 1.4293 0.7542 0.1797 0.030 Uiso 1 1 calc R . .
C2 C 1.0762(8) 0.2587(6) 0.08656(17) 0.0171(12) Uani 1 1 d . . .
C13 C 1.8226(9) 0.6221(9) 0.0903(2) 0.0352(18) Uani 1 1 d . . .
H13A H 1.8340 0.5474 0.0703 0.053 Uiso 1 1 calc R . .
H13B H 1.9009 0.6094 0.1117 0.053 Uiso 1 1 calc R . .
H13C H 1.8387 0.7131 0.0773 0.053 Uiso 1 1 calc R . .
C12 C 1.5405(8) 0.5228(7) 0.09293(18) 0.0213(15) Uani 1 1 d . . .
H12 H 1.5685 0.4645 0.0709 0.026 Uiso 1 1 calc R . .
C5 C 1.2692(8) 0.4127(6) 0.09246(17) 0.0178(13) Uani 1 1 d . . .
C9 C 1.6124(8) 0.7066(7) 0.14171(19) 0.0257(15) Uani 1 1 d . . .
C10 C 1.7335(8) 0.8096(8) 0.1594(2) 0.0329(15) Uani 1 1 d . . .
H10A H 1.7789 0.8661 0.1377 0.049 Uiso 1 1 calc R . .
H10B H 1.8173 0.7570 0.1730 0.049 Uiso 1 1 calc R . .
H10C H 1.6814 0.8712 0.1789 0.049 Uiso 1 1 calc R . .
C4 C 1.1372(7) 0.1773(7) 0.01057(18) 0.0215(14) Uani 1 1 d . . .
C7 C 1.3457(9) 0.6032(7) 0.14156(18) 0.0223(15) Uani 1 1 d . . .
H7 H 1.2426 0.6001 0.1526 0.027 Uiso 1 1 calc R . .
C3 C 1.1567(8) 0.2590(6) 0.04971(18) 0.0192(14) Uani 1 1 d . . .
C11 C 1.6542(9) 0.6163(7) 0.1089(2) 0.0265(15) Uani 1 1 d . . .
N1 N 1.1471(6) 0.3558(5) 0.11254(15) 0.0163(11) Uani 1 1 d . . .
N2 N 1.2792(6) 0.3562(5) 0.05365(14) 0.0190(11) Uani 1 1 d . . .
O5 O 0.8561(5) 0.4401(4) 0.19125(13) 0.0205(10) Uani 1 1 d . . .
O6 O 0.6991(5) 0.5384(5) 0.23887(14) 0.0266(11) Uani 1 1 d . . .
C14 C 0.7272(8) 0.4496(7) 0.20986(18) 0.0193(13) Uani 1 1 d . . .
N5 N 0.6009(6) 0.2519(5) 0.16773(14) 0.0146(11) Uani 1 1 d . . .
C16 C 0.5899(7) 0.3594(6) 0.19714(17) 0.0169(12) Uani 1 1 d . . .
C15 C 0.4306(8) 0.3637(6) 0.20816(16) 0.0148(12) Uani 1 1 d . . .
C17 C 0.3368(8) 0.4640(7) 0.23397(18) 0.0191(14) Uani 1 1 d . . .
C19 C 0.4509(7) 0.1972(7) 0.16219(16) 0.0165(12) Uani 1 1 d . . .
N4 N 0.3468(6) 0.2632(5) 0.18649(15) 0.0168(11) Uani 1 1 d . . .
C20 C 0.4058(7) 0.0875(6) 0.13217(18) 0.0158(12) Uani 1 1 d . . .
C21 C 0.4944(8) 0.0686(7) 0.09617(19) 0.0211(14) Uani 1 1 d . . .
H21 H 0.5884 0.1204 0.0921 0.025 Uiso 1 1 calc R . .
C25 C 0.4429(8) -0.0270(6) 0.06632(18) 0.0228(14) Uani 1 1 d . . .
C22 C 0.2680(8) 0.0090(6) 0.13863(19) 0.0198(14) Uani 1 1 d . . .
H22 H 0.2094 0.0200 0.1628 0.024 Uiso 1 1 calc R . .
C23 C 0.2177(8) -0.0871(6) 0.10854(19) 0.0214(14) Uani 1 1 d . . .
H23 H 0.1248 -0.1401 0.1129 0.026 Uiso 1 1 calc R . .
C24 C 0.3030(9) -0.1054(7) 0.0723(2) 0.0251(15) Uani 1 1 d . . .
C26 C 0.5401(9) -0.0449(8) 0.0277(2) 0.0366(18) Uani 1 1 d . . .
H26A H 0.6331 0.0156 0.0289 0.055 Uiso 1 1 calc R . .
H26B H 0.4758 -0.0190 0.0043 0.055 Uiso 1 1 calc R . .
H26C H 0.5733 -0.1428 0.0251 0.055 Uiso 1 1 calc R . .
C27 C 0.2400(8) -0.2065(7) 0.04022(18) 0.0247(14) Uani 1 1 d . . .
H27A H 0.1460 -0.2538 0.0505 0.037 Uiso 1 1 calc R . .
H27B H 0.3209 -0.2762 0.0338 0.037 Uiso 1 1 calc R . .
H27C H 0.2130 -0.1540 0.0158 0.037 Uiso 1 1 calc R . .
O14 O 0.4143(5) 0.5548(5) 0.25655(13) 0.0237(10) Uani 1 1 d . . .
H14 H 0.5111 0.5433 0.2534 0.036 Uiso 1 1 calc R . .
O15 O 0.1893(5) 0.4633(5) 0.23207(12) 0.0223(10) Uani 1 1 d . . .
O17 O 1.0226(6) 0.1516(5) 0.23157(15) 0.0365(13) 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 O5 2.229(4) . ?
Cd1 O17 2.252(4) . ?
Cd1 N4 2.309(5) 1_655 ?
Cd1 O1 2.323(4) . ?
Cd1 N1 2.335(5) . ?
Cd1 O15 2.411(4) 1_655 ?
O4 C4 1.205(7) . ?
O1 C1 1.276(7) . ?
O2 C1 1.251(7) . ?
O3 C4 1.317(8) . ?
C6 C12 1.388(9) . ?
C6 C7 1.391(9) . ?
C6 C5 1.460(9) . ?
C1 C2 1.479(8) . ?
C8 C7 1.381(9) . ?
C8 C9 1.389(9) . ?
C2 C3 1.372(8) . ?
C2 N1 1.374(8) . ?
C13 C11 1.527(9) . ?
C12 C11 1.390(9) . ?
C5 N1 1.320(8) . ?
C5 N2 1.370(7) . ?
C9 C11 1.405(9) . ?
C9 C10 1.509(9) . ?
C4 C3 1.493(8) . ?
C3 N2 1.372(8) . ?
O5 C14 1.235(7) . ?
O6 C14 1.278(7) . ?
C14 C16 1.480(9) . ?
N5 C19 1.361(7) . ?
N5 C16 1.390(7) . ?
C16 C15 1.374(9) . ?
C15 N4 1.366(7) . ?
C15 C17 1.481(8) . ?
C17 O15 1.229(8) . ?
C17 O14 1.295(7) . ?
C19 N4 1.325(7) . ?
C19 C20 1.465(8) . ?
N4 Cd1 2.309(5) 1_455 ?
C20 C22 1.378(9) . ?
C20 C21 1.394(8) . ?
C21 C25 1.387(9) . ?
C25 C24 1.391(10) . ?
C25 C26 1.503(9) . ?
C22 C23 1.392(9) . ?
C23 C24 1.386(9) . ?
C24 C27 1.501(9) . ?
O15 Cd1 2.411(4) 1_455 ?

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
O5 Cd1 O17 95.08(16) . . ?
O5 Cd1 N4 152.72(16) . 1_655 ?
O17 Cd1 N4 90.64(17) . 1_655 ?
O5 Cd1 O1 82.85(15) . . ?
O17 Cd1 O1 88.40(17) . . ?
N4 Cd1 O1 124.03(16) 1_655 . ?
O5 Cd1 N1 104.52(16) . . ?
O17 Cd1 N1 150.53(18) . . ?
N4 Cd1 N1 82.00(17) 1_655 . ?
O1 Cd1 N1 72.76(15) . . ?
O5 Cd1 O15 83.17(14) . 1_655 ?
O17 Cd1 O15 87.63(17) . 1_655 ?
N4 Cd1 O15 70.42(16) 1_655 1_655 ?
O1 Cd1 O15 165.06(14) . 1_655 ?
N1 Cd1 O15 116.05(16) . 1_655 ?
C1 O1 Cd1 116.2(4) . . ?
C12 C6 C7 118.3(6) . . ?
C12 C6 C5 121.3(6) . . ?
C7 C6 C5 120.5(6) . . ?
O2 C1 O1 123.4(5) . . ?
O2 C1 C2 119.6(5) . . ?
O1 C1 C2 117.0(5) . . ?
C7 C8 C9 122.0(6) . . ?
C3 C2 N1 108.9(5) . . ?
C3 C2 C1 130.0(5) . . ?
N1 C2 C1 120.9(5) . . ?
C6 C12 C11 121.9(6) . . ?
N1 C5 N2 110.3(5) . . ?
N1 C5 C6 126.4(5) . . ?
N2 C5 C6 123.2(5) . . ?
C8 C9 C11 118.1(6) . . ?
C8 C9 C10 121.4(6) . . ?
C11 C9 C10 120.5(6) . . ?
O4 C4 O3 122.4(6) . . ?
O4 C4 C3 121.6(6) . . ?
O3 C4 C3 116.0(5) . . ?
C8 C7 C6 120.2(6) . . ?
C2 C3 N2 106.5(5) . . ?
C2 C3 C4 133.5(6) . . ?
N2 C3 C4 120.0(5) . . ?
C12 C11 C9 119.5(6) . . ?
C12 C11 C13 120.0(6) . . ?
C9 C11 C13 120.4(6) . . ?
C5 N1 C2 107.1(5) . . ?
C5 N1 Cd1 138.0(4) . . ?
C2 N1 Cd1 110.1(4) . . ?
C5 N2 C3 107.2(5) . . ?
C14 O5 Cd1 145.7(4) . . ?
O5 C14 O6 124.5(6) . . ?
O5 C14 C16 119.6(5) . . ?
O6 C14 C16 115.9(5) . . ?
C19 N5 C16 107.6(5) . . ?
C15 C16 N5 105.3(5) . . ?
C15 C16 C14 131.0(5) . . ?
N5 C16 C14 123.6(5) . . ?
N4 C15 C16 109.8(5) . . ?
N4 C15 C17 117.3(5) . . ?
C16 C15 C17 132.5(6) . . ?
O15 C17 O14 122.0(6) . . ?
O15 C17 C15 119.7(6) . . ?
O14 C17 C15 118.3(6) . . ?
N4 C19 N5 110.3(5) . . ?
N4 C19 C20 123.7(5) . . ?
N5 C19 C20 125.9(5) . . ?
C19 N4 C15 107.0(5) . . ?
C19 N4 Cd1 132.6(4) . 1_455 ?
C15 N4 Cd1 114.8(4) . 1_455 ?
C22 C20 C21 120.0(6) . . ?
C22 C20 C19 119.1(6) . . ?
C21 C20 C19 120.8(5) . . ?
C25 C21 C20 120.3(6) . . ?
C21 C25 C24 120.1(6) . . ?
C21 C25 C26 119.3(6) . . ?
C24 C25 C26 120.5(6) . . ?
C20 C22 C23 119.2(6) . . ?
C24 C23 C22 121.5(6) . . ?
C23 C24 C25 118.8(6) . . ?
C23 C24 C27 119.3(6) . . ?
C25 C24 C27 121.9(6) . . ?
C17 O15 Cd1 115.6(4) . 1_455 ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.767
_refine_diff_density_min         -0.665
_refine_diff_density_rms         0.101
