# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_D-1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C14 H11 Cd N2 O7), O'
_chemical_formula_sum            'C28 H22 Cd2 N4 O15'
_chemical_formula_weight         879.32

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 '

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

_cell_length_a                   21.9728(11)
_cell_length_b                   8.4040(4)
_cell_length_c                   11.7030(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2161.07(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7985
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      28.45

_exptl_crystal_description       plate
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1820
_exptl_absorpt_coefficient_mu    1.042
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.652
_exptl_absorpt_correction_T_max  0.779
_exptl_absorpt_process_details   multi-scan

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10663
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         28.51
_reflns_number_total             5504
_reflns_number_gt                4957
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
loop_
  _platon_squeeze_void_nr
  _platon_squeeze_void_average_x
  _platon_squeeze_void_average_y
  _platon_squeeze_void_average_z
  _platon_squeeze_void_volume
  _platon_squeeze_void_count_electrons
  _platon_squeeze_void_content
   1  0.500 -0.010  0.551       328        91 ' '
   2  0.000 -0.051  0.449       328        91 ' '
_platon_squeeze_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)+(0.0930P)²+1.6295P] 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 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(6)
_refine_ls_number_reflns         5196
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1404
_refine_ls_wR_factor_gt          0.1388
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.135
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.208680(14) 1.11021(4) -0.02065(3) 0.02987(12) Uani 1 1 d . . .
C3 C 0.2104(3) 1.1023(9) 0.4164(5) 0.0566(16) Uani 1 1 d . . .
C4 C 0.2633(4) 1.069(2) 0.3494(8) 0.104(6) Uani 1 1 d . . .
H4 H 0.2999 1.0420 0.3842 0.125 Uiso 1 1 calc R . .
C5 C 0.2588(4) 1.077(2) 0.2367(6) 0.087(4) Uani 1 1 d . . .
H5 H 0.2941 1.0576 0.1951 0.104 Uiso 1 1 calc R . .
C2 C 0.1568(3) 1.112(3) 0.3568(5) 0.095(4) Uani 1 1 d . . .
H2 H 0.1196 1.1031 0.3943 0.114 Uiso 1 1 calc R . .
C1 C 0.1592(4) 1.136(2) 0.2394(7) 0.093(5) Uani 1 1 d . . .
H1 H 0.1245 1.1721 0.2020 0.112 Uiso 1 1 calc R . .
C6 C 0.2105(3) 1.0991(9) 0.5429(5) 0.0572(16) Uani 1 1 d . . .
C8 C 0.2601(4) 1.076(2) 0.6042(7) 0.114(6) Uani 1 1 d . . .
H8 H 0.2965 1.0551 0.5665 0.136 Uiso 1 1 calc R . .
C7 C 0.1602(4) 1.132(3) 0.6052(8) 0.154(8) Uani 1 1 d . . .
H7 H 0.1254 1.1715 0.5700 0.184 Uiso 1 1 calc R . .
N1 N 0.2095(2) 1.1087(7) 0.1782(4) 0.0484(11) Uani 1 1 d . . .
C10 C 0.1614(4) 1.107(3) -0.2761(6) 0.135(7) Uani 1 1 d . . .
H10 H 0.1246 1.0953 -0.2378 0.162 Uiso 1 1 calc R . .
C9 C 0.2602(4) 1.082(3) -0.2786(9) 0.111(6) Uani 1 1 d . . .
H9 H 0.2971 1.0717 -0.2404 0.133 Uiso 1 1 calc R . .
N2 N 0.2106(3) 1.1006(7) -0.2181(4) 0.0542(13) Uani 1 1 d . . .
O4 O 0.11241(15) 0.9739(5) -0.0198(5) 0.0464(10) Uani 1 1 d . . .
O2 O 0.21929(14) 0.8384(5) -0.0011(4) 0.0389(9) Uani 1 1 d . . .
O3 O 0.14070(19) 1.3124(5) -0.0289(6) 0.0694(17) Uani 1 1 d . . .
C11 C 0.1749(2) 0.7477(6) 0.0133(5) 0.0346(10) Uani 1 1 d . . .
O1 O 0.18192(16) 0.6010(4) 0.0317(4) 0.0435(9) Uani 1 1 d . . .
C12 C 0.1103(2) 0.8153(6) 0.0105(6) 0.0392(12) Uani 1 1 d . . .
H12 H 0.0935 0.8084 0.0879 0.047 Uiso 1 1 calc R . .
C13 C 0.0710(3) 0.7148(9) -0.0672(10) 0.075(3) Uani 1 1 d . . .
H13 H 0.0732 0.6061 -0.0372 0.090 Uiso 1 1 calc R . .
O5 O 0.0953(3) 0.7089(13) -0.1762(8) 0.127(4) Uani 1 1 d . . .
H5A H 0.1162 0.6287 -0.1829 0.190 Uiso 1 1 calc R . .
C14 C 0.0028(3) 0.7688(9) -0.0537(10) 0.078(3) Uani 1 1 d D . .
O6 O -0.0190(3) 0.818(2) 0.0185(10) 0.203(7) Uani 1 1 d . . .
O8 O 0.0000 0.0000 0.2475(15) 0.34(3) Uani 1 2 d S . .
O7 O -0.0248(5) 0.787(3) -0.1496(12) 0.295(13) Uani 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cd1 0.02026(15) 0.03154(18) 0.03780(18) -0.00061(14) -0.00073(12) -0.00242(13)
C3 0.051(3) 0.085(5) 0.033(3) 0.000(3) 0.000(2) -0.007(8)
C4 0.053(4) 0.204(17) 0.056(4) 0.023(8) -0.005(4) -0.004(7)
C5 0.054(4) 0.173(13) 0.033(3) -0.001(5) 0.003(3) 0.027(7)
C2 0.048(4) 0.209(13) 0.027(3) -0.018(7) 0.009(3) -0.017(7)
C1 0.045(4) 0.181(14) 0.053(4) 0.000(7) -0.005(3) 0.027(7)
C6 0.050(3) 0.083(5) 0.039(3) -0.002(3) -0.002(2) -0.003(7)
C8 0.058(5) 0.238(18) 0.045(4) -0.024(7) -0.006(4) 0.069(8)
C7 0.060(5) 0.36(3) 0.044(4) -0.003(11) 0.001(4) 0.083(11)
N1 0.046(2) 0.067(3) 0.032(2) 0.001(2) 0.0032(19) 0.003(6)
C10 0.053(4) 0.33(2) 0.022(3) 0.033(8) 0.003(3) 0.015(10)
C9 0.050(4) 0.211(18) 0.072(6) -0.009(9) -0.007(4) 0.042(8)
N2 0.045(3) 0.074(4) 0.044(3) 0.003(2) -0.003(2) -0.020(6)
O4 0.0209(15) 0.0347(19) 0.084(3) 0.005(2) 0.0015(19) 0.0019(13)
O2 0.0158(13) 0.0345(17) 0.066(3) -0.0011(18) 0.0002(14) 0.0003(13)
O3 0.0305(19) 0.037(2) 0.140(5) -0.008(3) -0.011(3) -0.0014(16)
C11 0.023(2) 0.032(2) 0.049(3) -0.004(2) -0.003(2) 0.0033(17)
O1 0.0267(16) 0.0359(19) 0.068(3) 0.003(2) -0.0078(17) 0.0067(15)
C12 0.021(2) 0.034(2) 0.063(3) -0.001(3) 0.004(2) 0.0025(17)
C13 0.023(3) 0.051(4) 0.151(9) -0.023(5) -0.028(4) 0.008(2)
O5 0.063(4) 0.173(9) 0.144(7) -0.095(7) -0.032(5) 0.017(5)
C14 0.024(3) 0.048(4) 0.161(10) -0.026(5) -0.024(4) 0.008(3)
O6 0.044(4) 0.386(19) 0.180(10) 0.082(13) 0.030(5) 0.095(7)
O8 0.134(14) 0.78(8) 0.102(11) 0.000 0.000 -0.02(3)
O7 0.093(7) 0.54(4) 0.257(15) -0.16(2) -0.094(9) 0.136(13)

_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 O3 2.264(4) . ?
Cd1 O2 2.308(4) . ?
Cd1 N2 2.313(5) . ?
Cd1 N1 2.328(4) . ?
Cd1 O4 2.406(4) . ?
Cd1 O1 2.409(4) 3 ?
Cd1 O2 2.499(4) 3 ?
C3 C2 1.371(10) . ?
C3 C4 1.429(12) . ?
C3 C6 1.481(8) . ?
C4 C5 1.324(12) . ?
C5 N1 1.311(9) . ?
C2 C1 1.390(11) . ?
C1 N1 1.335(9) . ?
C6 C8 1.320(10) . ?
C6 C7 1.352(11) . ?
C8 C9 1.373(14) 1_556 ?
C7 C10 1.406(12) 1_556 ?
C10 N2 1.278(9) . ?
C10 C7 1.406(12) 1_554 ?
C9 N2 1.308(11) . ?
C9 C8 1.373(14) 1_554 ?
O4 C12 1.380(7) . ?
O2 C11 1.248(6) . ?
O2 Cd1 2.499(4) 3_545 ?
C11 O1 1.261(6) . ?
C11 C12 1.530(6) . ?
O1 Cd1 2.409(4) 3_545 ?
C12 C13 1.511(9) . ?
C13 O5 1.384(14) . ?
C13 C14 1.574(9) . ?
C14 O6 1.055(15) . ?
C14 O7 1.285(13) . ?

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
O3 Cd1 O2 144.46(14) . . ?
O3 Cd1 N2 89.7(2) . . ?
O2 Cd1 N2 93.61(19) . . ?
O3 Cd1 N1 93.0(2) . . ?
O2 Cd1 N1 83.96(18) . . ?
N2 Cd1 N1 177.3(2) . . ?
O3 Cd1 O4 77.15(14) . . ?
O2 Cd1 O4 67.48(12) . . ?
N2 Cd1 O4 90.24(19) . . ?
N1 Cd1 O4 89.98(19) . . ?
O3 Cd1 O1 132.85(14) . 3 ?
O2 Cd1 O1 82.69(12) . 3 ?
N2 Cd1 O1 85.78(18) . 3 ?
N1 Cd1 O1 92.66(16) . 3 ?
O4 Cd1 O1 149.60(13) . 3 ?
O3 Cd1 O2 81.16(14) . 3 ?
O2 Cd1 O2 133.27(5) . 3 ?
N2 Cd1 O2 96.69(16) . 3 ?
N1 Cd1 O2 84.13(17) . 3 ?
O4 Cd1 O2 157.18(13) . 3 ?
O1 Cd1 O2 53.00(12) 3 3 ?
C2 C3 C4 115.5(6) . . ?
C2 C3 C6 120.6(7) . . ?
C4 C3 C6 123.0(7) . . ?
C5 C4 C3 118.5(9) . . ?
N1 C5 C4 126.3(8) . . ?
C3 C2 C1 118.6(7) . . ?
N1 C1 C2 122.4(9) . . ?
C8 C6 C7 114.3(7) . . ?
C8 C6 C3 123.1(7) . . ?
C7 C6 C3 122.3(7) . . ?
C6 C8 C9 122.6(8) . 1_556 ?
C6 C7 C10 119.1(10) . 1_556 ?
C5 N1 C1 116.1(6) . . ?
C5 N1 Cd1 122.0(4) . . ?
C1 N1 Cd1 121.9(5) . . ?
N2 C10 C7 123.2(8) . 1_554 ?
N2 C9 C8 122.9(8) . 1_554 ?
C10 N2 C9 115.1(7) . . ?
C10 N2 Cd1 120.9(5) . . ?
C9 N2 Cd1 124.0(6) . . ?
C12 O4 Cd1 119.4(3) . . ?
C11 O2 Cd1 122.6(3) . . ?
C11 O2 Cd1 90.7(3) . 3_545 ?
Cd1 O2 Cd1 146.47(14) . 3_545 ?
O2 C11 O1 121.7(4) . . ?
O2 C11 C12 119.7(5) . . ?
O1 C11 C12 118.6(4) . . ?
C11 O1 Cd1 94.6(3) . 3_545 ?
O4 C12 C13 113.9(6) . . ?
O4 C12 C11 109.4(4) . . ?
C13 C12 C11 109.6(5) . . ?
O5 C13 C12 110.8(7) . . ?
O5 C13 C14 118.0(8) . . ?
C12 C13 C14 108.8(7) . . ?
O6 C14 O7 116.1(9) . . ?
O6 C14 C13 128.7(10) . . ?
O7 C14 C13 113.4(10) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        28.51
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         1.237
_refine_diff_density_min         -0.801
_refine_diff_density_rms         0.246
_database_code_depnum_ccdc_archive 'CCDC 986613'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_L-1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C14 H11 Cd N2 O7), O'
_chemical_formula_sum            'C28 H22 Cd2 N4 O15'
_chemical_formula_weight         879.32

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 '

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

_cell_length_a                   21.9953(12)
_cell_length_b                   8.4064(5)
_cell_length_c                   11.7118(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2165.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9074
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      29.63

_exptl_crystal_description       plate
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             868
_exptl_absorpt_coefficient_mu    1.040
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.653
_exptl_absorpt_correction_T_max  0.779
_exptl_absorpt_process_details   multi-scan

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36644
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0180
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         29.82
_reflns_number_total             6225
_reflns_number_gt                5664
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
loop_
  _platon_squeeze_void_nr
  _platon_squeeze_void_average_x
  _platon_squeeze_void_average_y
  _platon_squeeze_void_average_z
  _platon_squeeze_void_volume
  _platon_squeeze_void_count_electrons
  _platon_squeeze_void_content
   1  0.000 -0.052  0.046       331        89 ' '
   2  0.500 -0.005 -0.046       331        89 ' '
_platon_squeeze_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)+(0.0965P)²+1.6580P] 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   -0.03(5)
_refine_ls_number_reflns         5983
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1318
_refine_ls_wR_factor_gt          0.1296
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.208799(11) 1.10938(3) 0.52013(3) 0.03047(9) Uani 1 1 d . . .
C3 C 0.2105(3) 1.0977(8) 0.9566(5) 0.0589(14) Uani 1 1 d . . .
C7 C 0.2107(3) 1.0994(8) 1.0831(4) 0.0568(13) Uani 1 1 d . . .
C5 C 0.2621(3) 1.095(3) 0.7776(8) 0.122(6) Uani 1 1 d . . .
H5 H 0.2994 1.1010 0.7404 0.147 Uiso 1 1 calc R . .
C8 C 0.2632(4) 1.068(2) 1.1470(7) 0.100(5) Uani 1 1 d . . .
H8 H 0.3000 1.0446 1.1115 0.121 Uiso 1 1 calc R . .
C2 C 0.1598(4) 1.122(3) 0.8945(7) 0.144(7) Uani 1 1 d . . .
H2 H 0.1243 1.1595 0.9281 0.173 Uiso 1 1 calc R . .
C4 C 0.2605(3) 1.080(2) 0.8954(7) 0.115(5) Uani 1 1 d . . .
H4 H 0.2965 1.0566 0.9335 0.138 Uiso 1 1 calc R . .
C10 C 0.2582(3) 1.0715(13) 0.2644(5) 0.078(3) Uani 1 1 d . . .
H10 H 0.2927 1.0459 0.3064 0.094 Uiso 1 1 calc R . .
C9 C 0.1596(3) 1.1381(17) 0.2586(6) 0.085(3) Uani 1 1 d . . .
H9 H 0.1254 1.1775 0.2957 0.102 Uiso 1 1 calc R . .
C6 C 0.1566(3) 1.114(2) 1.1449(5) 0.094(3) Uani 1 1 d . . .
H6 H 0.1192 1.1078 1.1082 0.112 Uiso 1 1 calc R . .
N2 N 0.2114(2) 1.0997(6) 0.7174(4) 0.0526(10) Uani 1 1 d . . .
N1 N 0.20987(19) 1.1076(6) 0.3210(3) 0.0484(9) Uani 1 1 d . . .
O1 O 0.21951(11) 0.8375(3) 0.5014(3) 0.0387(7) Uani 1 1 d . . .
O2 O 0.11243(13) 0.9727(4) 0.5200(4) 0.0484(9) Uani 1 1 d . . .
O7 O 0.14069(15) 1.3110(4) 0.5286(6) 0.0722(16) Uani 1 1 d . . .
C13 C 0.11028(16) 0.8131(4) 0.4903(5) 0.0380(10) Uani 1 1 d . . .
H13 H 0.0940 0.8066 0.4126 0.046 Uiso 1 1 calc R . .
C12 C 0.17476(16) 0.7461(4) 0.4876(5) 0.0349(8) Uani 1 1 d . . .
C14 C 0.0706(2) 0.7136(7) 0.5646(9) 0.076(2) Uani 1 1 d . . .
H14 H 0.0718 0.6046 0.5351 0.091 Uiso 1 1 calc R . .
O3 O 0.18177(13) 0.6002(3) 0.4690(3) 0.0443(7) Uani 1 1 d . . .
O4 O 0.0954(3) 0.7116(11) 0.6769(7) 0.123(3) Uani 1 1 d . . .
H4A H 0.1179 0.6345 0.6839 0.185 Uiso 1 1 calc R . .
C15 C 0.0030(2) 0.7711(7) 0.5600(9) 0.076(2) Uani 1 1 d . . .
O6 O -0.0181(3) 0.8195(17) 0.4750(9) 0.195(6) Uani 1 1 d . . .
C1 C 0.1626(3) 1.088(2) 0.7761(6) 0.125(6) Uani 1 1 d . . .
H1 H 0.1271 1.0563 0.7393 0.150 Uiso 1 1 calc R . .
O5 O -0.0252(4) 0.774(2) 0.6315(12) 0.285(11) Uani 1 1 d . . .
O8 O 0.0000 0.0000 0.2447(15) 0.40(3) Uani 1 2 d S . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cd1 0.02135(12) 0.03025(13) 0.03981(16) 0.00055(10) 0.00065(10) -0.00229(9)
C3 0.051(3) 0.084(4) 0.042(3) 0.000(2) -0.003(2) 0.003(5)
C7 0.052(3) 0.081(4) 0.037(3) 0.002(2) 0.002(2) -0.005(5)
C5 0.043(3) 0.255(17) 0.069(5) 0.015(9) 0.004(3) -0.018(7)
C8 0.058(4) 0.190(14) 0.053(4) -0.019(6) 0.006(3) 0.001(6)
C2 0.059(4) 0.32(2) 0.051(4) -0.009(10) -0.003(3) 0.062(9)
C4 0.058(4) 0.243(16) 0.045(3) 0.022(7) 0.001(3) 0.058(7)
C10 0.055(3) 0.144(9) 0.035(3) 0.002(4) -0.005(2) 0.036(5)
C9 0.044(3) 0.154(10) 0.057(4) 0.003(5) 0.003(3) 0.026(5)
C6 0.045(3) 0.197(11) 0.039(3) 0.008(6) -0.009(2) -0.013(5)
N2 0.045(2) 0.069(3) 0.044(2) -0.0005(19) 0.0011(18) -0.010(4)
N1 0.047(2) 0.063(2) 0.0355(19) 0.0005(17) -0.0070(16) 0.004(4)
O1 0.0200(10) 0.0309(12) 0.065(2) 0.0008(14) 0.0005(11) -0.0002(10)
O2 0.0218(11) 0.0342(14) 0.089(3) -0.0058(17) 0.0001(16) 0.0027(9)
O7 0.0302(14) 0.0327(15) 0.154(5) 0.006(2) 0.015(2) 0.0002(11)
C13 0.0196(14) 0.0319(17) 0.063(3) -0.0035(18) -0.0013(16) 0.0015(12)
C12 0.0245(15) 0.0279(15) 0.052(2) 0.0033(16) 0.0038(17) -0.0007(12)
C14 0.029(2) 0.047(3) 0.151(8) 0.024(4) 0.029(3) 0.0064(19)
O3 0.0275(12) 0.0307(13) 0.075(2) 0.0004(17) 0.0062(14) 0.0051(10)
O4 0.062(3) 0.175(8) 0.134(6) 0.085(6) 0.031(4) 0.020(4)
C15 0.025(2) 0.044(2) 0.161(8) 0.020(4) 0.023(4) 0.0043(17)
O6 0.043(3) 0.363(15) 0.179(9) -0.067(12) -0.028(4) 0.080(6)
C1 0.060(4) 0.286(19) 0.028(3) -0.033(7) 0.002(3) -0.043(8)
O5 0.078(5) 0.54(3) 0.238(13) 0.129(17) 0.073(7) 0.125(10)
O8 0.227(19) 0.88(9) 0.098(11) 0.000 0.000 0.04(4)

_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 O7 2.264(3) . ?
Cd1 O1 2.308(3) . ?
Cd1 N2 2.313(5) . ?
Cd1 N1 2.332(4) . ?
Cd1 O2 2.411(3) . ?
Cd1 O3 2.412(3) 3_556 ?
Cd1 O1 2.495(3) 3_556 ?
C3 C4 1.321(9) . ?
C3 C2 1.345(9) . ?
C3 C7 1.482(7) . ?
C7 C6 1.398(9) . ?
C7 C8 1.401(11) . ?
C5 N2 1.320(9) . ?
C5 C4 1.386(12) . ?
C8 C10 1.381(11) 1_556 ?
C2 C1 1.416(12) . ?
C10 N1 1.289(8) . ?
C10 C8 1.381(11) 1_554 ?
C9 C6 1.348(11) 1_554 ?
C9 N1 1.351(8) . ?
C6 C9 1.348(11) 1_556 ?
N2 C1 1.278(8) . ?
O1 C12 1.259(4) . ?
O1 Cd1 2.495(3) 3_546 ?
O2 C13 1.387(5) . ?
C13 C14 1.489(7) . ?
C13 C12 1.526(5) . ?
C12 O3 1.254(5) . ?
C14 O4 1.424(12) . ?
C14 C15 1.565(8) . ?
O3 Cd1 2.411(3) 3_546 ?
C15 O5 1.041(13) . ?
C15 O6 1.171(13) . ?

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
O7 Cd1 O1 144.37(11) . . ?
O7 Cd1 N2 89.9(2) . . ?
O1 Cd1 N2 93.32(16) . . ?
O7 Cd1 N1 93.2(2) . . ?
O1 Cd1 N1 84.11(15) . . ?
N2 Cd1 N1 176.90(17) . . ?
O7 Cd1 O2 77.00(11) . . ?
O1 Cd1 O2 67.53(9) . . ?
N2 Cd1 O2 90.31(16) . . ?
N1 Cd1 O2 90.30(16) . . ?
O7 Cd1 O3 133.00(11) . 3_556 ?
O1 Cd1 O3 82.63(9) . 3_556 ?
N2 Cd1 O3 85.51(15) . 3_556 ?
N1 Cd1 O3 92.43(14) . 3_556 ?
O2 Cd1 O3 149.58(10) . 3_556 ?
O7 Cd1 O1 81.22(11) . 3_556 ?
O1 Cd1 O1 133.38(4) . 3_556 ?
N2 Cd1 O1 96.44(14) . 3_556 ?
N1 Cd1 O1 84.13(14) . 3_556 ?
O2 Cd1 O1 157.17(10) . 3_556 ?
O3 Cd1 O1 53.06(9) 3_556 3_556 ?
C4 C3 C2 114.4(7) . . ?
C4 C3 C7 122.7(6) . . ?
C2 C3 C7 122.8(6) . . ?
C6 C7 C8 116.2(6) . . ?
C6 C7 C3 121.0(6) . . ?
C8 C7 C3 122.3(6) . . ?
N2 C5 C4 120.8(7) . . ?
C10 C8 C7 117.5(7) 1_556 . ?
C3 C2 C1 117.6(9) . . ?
C3 C4 C5 123.4(7) . . ?
N1 C10 C8 125.7(7) . 1_554 ?
C6 C9 N1 123.1(7) 1_554 . ?
C9 C6 C7 118.9(6) 1_556 . ?
C1 N2 C5 114.9(6) . . ?
C1 N2 Cd1 121.3(4) . . ?
C5 N2 Cd1 123.7(5) . . ?
C10 N1 C9 116.2(5) . . ?
C10 N1 Cd1 121.6(4) . . ?
C9 N1 Cd1 122.1(4) . . ?
C12 O1 Cd1 122.5(2) . . ?
C12 O1 Cd1 90.7(2) . 3_546 ?
Cd1 O1 Cd1 146.62(12) . 3_546 ?
C13 O2 Cd1 119.4(2) . . ?
O2 C13 C14 114.6(5) . . ?
O2 C13 C12 109.3(3) . . ?
C14 C13 C12 110.5(4) . . ?
O3 C12 O1 121.5(3) . . ?
O3 C12 C13 118.6(3) . . ?
O1 C12 C13 119.9(3) . . ?
O4 C14 C13 108.7(5) . . ?
O4 C14 C15 113.6(7) . . ?
C13 C14 C15 111.3(5) . . ?
C12 O3 Cd1 94.7(2) . 3_546 ?
O5 C15 O6 116.2(8) . . ?
O5 C15 C14 122.9(11) . . ?
O6 C15 C14 120.9(8) . . ?
N2 C1 C2 123.1(8) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        29.82
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.103
_refine_diff_density_min         -0.846
_refine_diff_density_rms         0.247
_database_code_depnum_ccdc_archive 'CCDC 986614'
