# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H9 Cd Cl N3 O4'
_chemical_formula_weight         455.11

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'
Cl Cl 0.1484 0.1585 '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           Tetragonal
_symmetry_space_group_name_H-M   I4(1)/a

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   22.0734(10)
_cell_length_b                   22.0734(10)
_cell_length_c                   16.1233(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     7855.8(8)
_cell_formula_units_Z            16
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8086
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      27.50

_exptl_crystal_description       cubic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3568
_exptl_absorpt_coefficient_mu    1.270
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7419
_exptl_absorpt_correction_T_max  0.7763
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24463
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4508
_reflns_number_gt                3833
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0665P)²+73.7500P] 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_number_reflns         4508
_refine_ls_number_parameters     227
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1349
_refine_ls_wR_factor_gt          0.1275
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.399
_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 0.421191(16) 0.011965(16) 0.05059(2) 0.01396(15) Uani 1 1 d . . .
N2 N 0.3672(2) 0.0632(2) -0.0467(3) 0.0171(9) Uani 1 1 d . . .
N1 N 0.4423(2) 0.1012(2) 0.1213(3) 0.0215(10) Uani 1 1 d . . .
C4 C 0.4873(3) 0.2190(2) 0.1436(4) 0.0210(11) Uani 1 1 d . . .
C12 C 0.3126(2) 0.0894(2) -0.0560(3) 0.0173(10) Uani 1 1 d . . .
C10 C 0.2098(4) 0.0267(4) 0.1082(5) 0.0440(19) Uani 1 1 d . . .
H10 H 0.2003 -0.0106 0.1318 0.053 Uiso 1 1 calc R . .
C5 C 0.4276(3) 0.2088(3) 0.1183(5) 0.0338(16) Uani 1 1 d . . .
H5 H 0.4017 0.2413 0.1086 0.041 Uiso 1 1 calc R . .
C7 C 0.2352(3) 0.1385(3) 0.0355(5) 0.0335(15) Uani 1 1 d . . .
H7 H 0.2432 0.1757 0.0107 0.040 Uiso 1 1 calc R . .
C13 C 0.3965(2) 0.0718(2) -0.1201(3) 0.0168(10) Uani 1 1 d . . .
C2 C 0.4982(3) 0.1111(3) 0.1511(4) 0.0211(11) Uani 1 1 d . . .
H2 H 0.5223 0.0778 0.1642 0.025 Uiso 1 1 calc R . .
C3 C 0.5218(3) 0.1688(3) 0.1631(4) 0.0241(12) Uani 1 1 d . . .
H3 H 0.5607 0.1735 0.1842 0.029 Uiso 1 1 calc R . .
C6 C 0.1928(4) 0.1346(4) 0.0991(6) 0.058(3) Uani 1 1 d . . .
H6 H 0.1723 0.1689 0.1173 0.070 Uiso 1 1 calc R . .
C8 C 0.2655(3) 0.0872(3) 0.0092(4) 0.0231(12) Uani 1 1 d . . .
C11 C 0.1817(4) 0.0789(5) 0.1347(6) 0.059(3) Uani 1 1 d . . .
C1 C 0.4074(3) 0.1502(3) 0.1080(5) 0.0349(16) Uani 1 1 d . . .
H1 H 0.3676 0.1442 0.0910 0.042 Uiso 1 1 calc R . .
C9 C 0.2524(3) 0.0312(3) 0.0457(4) 0.0266(13) Uani 1 1 d . . .
H9 H 0.2726 -0.0034 0.0277 0.032 Uiso 1 1 calc R . .
Cl1 Cl 0.13194(19) 0.07352(18) 0.2190(3) 0.1135(12) Uani 1 1 d U . .
O2 O 0.4128(2) 0.1047(2) -0.3000(3) 0.0283(10) Uani 1 1 d . . .
H2A H 0.4350 0.0856 -0.2689 0.042 Uiso 1 1 calc R . .
O1 O 0.48284(19) 0.0525(2) -0.2024(3) 0.0284(10) Uani 1 1 d . . .
N3 N 0.3057(2) 0.1151(2) -0.1309(3) 0.0159(9) Uani 1 1 d . . .
C14 C 0.3582(2) 0.1034(2) -0.1727(3) 0.0170(10) Uani 1 1 d . . .
C15 C 0.3638(3) 0.1206(3) -0.2602(4) 0.0205(11) Uani 1 1 d . . .
C16 C 0.4594(2) 0.0503(2) -0.1319(3) 0.0179(10) Uani 1 1 d . . .
O3 O 0.32236(19) 0.1482(2) -0.2945(3) 0.0234(9) Uani 1 1 d . . .
O4 O 0.48523(17) 0.02976(18) -0.0686(3) 0.0197(8) 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 N3 2.232(4) 8_444 ?
Cd1 N2 2.272(4) . ?
Cd1 O4 2.280(4) 9_655 ?
Cd1 N1 2.324(5) . ?
Cd1 O4 2.418(4) . ?
Cd1 O3 2.464(4) 8_444 ?
N2 C12 1.344(7) . ?
N2 C13 1.363(7) . ?
N1 C2 1.343(7) . ?
N1 C1 1.343(8) . ?
C4 C3 1.382(8) . ?
C4 C5 1.399(9) . ?
C4 C4 1.477(11) 6_554 ?
C12 N3 1.343(7) . ?
C12 C8 1.480(8) . ?
C10 C11 1.376(12) . ?
C10 C9 1.382(9) . ?
C5 C1 1.379(9) . ?
C7 C8 1.382(9) . ?
C7 C6 1.392(10) . ?
C13 C14 1.386(7) . ?
C13 C16 1.479(7) . ?
C2 C3 1.390(8) . ?
C6 C11 1.377(13) . ?
C8 C9 1.399(9) . ?
C11 Cl1 1.752(8) . ?
O2 C15 1.305(7) . ?
O1 C16 1.249(7) . ?
N3 C14 1.366(7) . ?
N3 Cd1 2.232(4) 7_444 ?
C14 C15 1.466(8) . ?
C15 O3 1.232(7) . ?
C16 O4 1.255(7) . ?
O3 Cd1 2.464(4) 7_444 ?
O4 Cd1 2.280(4) 9_655 ?

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 Cd1 N2 112.56(16) 8_444 . ?
N3 Cd1 O4 99.73(15) 8_444 9_655 ?
N2 Cd1 O4 139.87(15) . 9_655 ?
N3 Cd1 N1 115.80(17) 8_444 . ?
N2 Cd1 N1 91.25(17) . . ?
O4 Cd1 N1 95.67(16) 9_655 . ?
N3 Cd1 O4 145.73(15) 8_444 . ?
N2 Cd1 O4 71.18(15) . . ?
O4 Cd1 O4 68.73(16) 9_655 . ?
N1 Cd1 O4 97.78(16) . . ?
N3 Cd1 O3 71.87(15) 8_444 8_444 ?
N2 Cd1 O3 80.71(16) . 8_444 ?
O4 Cd1 O3 87.72(15) 9_655 8_444 ?
N1 Cd1 O3 170.77(16) . 8_444 ?
O4 Cd1 O3 75.42(14) . 8_444 ?
C12 N2 C13 105.6(4) . . ?
C12 N2 Cd1 139.6(4) . . ?
C13 N2 Cd1 114.8(3) . . ?
C2 N1 C1 117.0(5) . . ?
C2 N1 Cd1 119.7(4) . . ?
C1 N1 Cd1 119.3(4) . . ?
C3 C4 C5 117.1(5) . . ?
C3 C4 C4 122.3(7) . 6_554 ?
C5 C4 C4 120.5(6) . 6_554 ?
N2 C12 N3 112.6(5) . . ?
N2 C12 C8 122.4(5) . . ?
N3 C12 C8 124.9(5) . . ?
C11 C10 C9 118.2(7) . . ?
C1 C5 C4 119.4(6) . . ?
C8 C7 C6 120.0(7) . . ?
N2 C13 C14 108.1(5) . . ?
N2 C13 C16 120.9(5) . . ?
C14 C13 C16 131.0(5) . . ?
N1 C2 C3 122.8(5) . . ?
C4 C3 C2 119.9(5) . . ?
C11 C6 C7 118.8(7) . . ?
C7 C8 C9 119.7(6) . . ?
C7 C8 C12 122.0(6) . . ?
C9 C8 C12 118.2(5) . . ?
C10 C11 C6 122.5(7) . . ?
C10 C11 Cl1 117.8(7) . . ?
C6 C11 Cl1 119.7(7) . . ?
N1 C1 C5 123.4(6) . . ?
C10 C9 C8 120.6(6) . . ?
C12 N3 C14 105.5(4) . . ?
C12 N3 Cd1 139.1(4) . 7_444 ?
C14 N3 Cd1 115.4(3) . 7_444 ?
N3 C14 C13 108.2(5) . . ?
N3 C14 C15 119.9(5) . . ?
C13 C14 C15 131.8(5) . . ?
O3 C15 O2 121.8(5) . . ?
O3 C15 C14 119.9(5) . . ?
O2 C15 C14 118.4(5) . . ?
O1 C16 O4 124.5(5) . . ?
O1 C16 C13 119.6(5) . . ?
O4 C16 C13 115.9(5) . . ?
C15 O3 Cd1 112.5(4) . 7_444 ?
C16 O4 Cd1 131.4(4) . 9_655 ?
C16 O4 Cd1 116.1(3) . . ?
Cd1 O4 Cd1 111.27(16) 9_655 . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         3.184
_refine_diff_density_min         -2.074
_refine_diff_density_rms         0.164
_database_code_depnum_ccdc_archive 'CCDC 982162'
