# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_DG1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H22 Co N4 O10'
_chemical_formula_weight         537.35

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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   14.2985(4)
_cell_length_b                   12.5882(3)
_cell_length_c                   14.4371(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.0070(10)
_cell_angle_gamma                90.00
_cell_volume                     2409.23(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    250
_cell_measurement_theta_min      1.7
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1108
_exptl_absorpt_coefficient_mu    0.773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8476
_exptl_absorpt_correction_T_max  0.9427
_exptl_absorpt_process_details   
;
'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL 
SPACE EXPLORATION,
Bruker Analytical X-ray Systems, 1997
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(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            39620
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0183
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         27.54
_reflns_number_total             5542
_reflns_number_gt                4208
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'SMART APEX II (Bruker,2010)'
_computing_cell_refinement       'SMART APEX II'
_computing_data_reduction        'SAINT (Bruker,2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3v2 for windows (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2008)'

_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 > 2σ(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)+(0.0691P)²+1.7791P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5542
_refine_ls_number_parameters     348
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1347
_refine_ls_wR_factor_gt          0.1240
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
C1 C 1.1647(2) 0.3880(2) 0.67512(19) 0.0413(6) Uani 1 1 d . . .
H1 H 1.1181 0.3989 0.7051 0.050 Uiso 1 1 calc R . .
C2 C 1.2555(2) 0.3427(2) 0.73047(19) 0.0455(6) Uani 1 1 d . . .
H2 H 1.2700 0.3237 0.7967 0.055 Uiso 1 1 calc R . .
C3 C 1.3254(2) 0.3256(2) 0.68722(19) 0.0437(6) Uani 1 1 d . . .
H3 H 1.3870 0.2936 0.7233 0.052 Uiso 1 1 calc R . .
C4 C 1.30234(19) 0.3567(2) 0.58916(18) 0.0364(5) Uani 1 1 d . . .
C5 C 1.20766(18) 0.40149(19) 0.53774(17) 0.0342(5) Uani 1 1 d . . .
H5 H 1.1913 0.4212 0.4714 0.041 Uiso 1 1 calc R . .
C6 C 1.3762(2) 0.3467(2) 0.5420(2) 0.0428(6) Uani 1 1 d . . .
C7 C 1.4278(2) 0.4235(3) 0.3464(2) 0.0478(7) Uani 1 1 d . . .
C8 C 1.50347(19) 0.4207(2) 0.30146(19) 0.0400(6) Uani 1 1 d . . .
C9 C 1.6009(2) 0.3839(2) 0.3523(2) 0.0451(6) Uani 1 1 d . . .
H9 H 1.6207 0.3601 0.4179 0.054 Uiso 1 1 calc R . .
C10 C 1.6677(2) 0.3829(2) 0.3044(2) 0.0446(6) Uani 1 1 d . . .
H10 H 1.7337 0.3602 0.3377 0.054 Uiso 1 1 calc R . .
C11 C 1.6356(2) 0.4162(2) 0.2063(2) 0.0418(6) Uani 1 1 d . . .
H11 H 1.6809 0.4131 0.1740 0.050 Uiso 1 1 calc R . .
C12 C 1.47895(19) 0.4558(2) 0.20393(18) 0.0396(6) Uani 1 1 d . . .
H12 H 1.4146 0.4831 0.1704 0.048 Uiso 1 1 calc R . .
C13 C 0.87704(17) 0.33353(18) 0.55991(17) 0.0316(5) Uani 1 1 d . . .
C14 C 0.81709(18) 0.31022(19) 0.62435(18) 0.0343(5) Uani 1 1 d . . .
C15 C 0.7543(2) 0.2232(2) 0.6068(2) 0.0495(7) Uani 1 1 d . . .
H15 H 0.7487 0.1773 0.5546 0.059 Uiso 1 1 calc R . .
C16 C 0.6991(2) 0.2033(2) 0.6665(2) 0.0530(7) Uani 1 1 d . . .
H16 H 0.6574 0.1440 0.6540 0.064 Uiso 1 1 calc R . .
C17 C 0.7055(2) 0.2703(2) 0.7439(2) 0.0394(6) Uani 1 1 d . . .
C18 C 0.7683(2) 0.3575(2) 0.7610(2) 0.0528(8) Uani 1 1 d . . .
H18 H 0.7739 0.4034 0.8133 0.063 Uiso 1 1 calc R . .
C19 C 0.8229(2) 0.3777(2) 0.7018(2) 0.0509(7) Uani 1 1 d . . .
H19 H 0.8642 0.4373 0.7143 0.061 Uiso 1 1 calc R . .
C20 C 0.6432(2) 0.2507(2) 0.8073(2) 0.0431(6) Uani 1 1 d . . .
N1 N 1.13970(15) 0.41746(16) 0.57889(14) 0.0347(4) Uani 1 1 d . . .
N2 N 1.36017(18) 0.3880(2) 0.45806(18) 0.0533(6) Uani 1 1 d . . .
N3 N 1.44096(18) 0.3733(2) 0.42603(18) 0.0531(6) Uani 1 1 d . . .
N4 N 1.54231(16) 0.45258(17) 0.15536(15) 0.0370(5) Uani 1 1 d . . .
O1 O 0.92698(13) 0.41766(13) 0.57774(13) 0.0392(4) Uani 1 1 d . . .
O2 O 0.87297(16) 0.26928(14) 0.49160(15) 0.0453(5) Uani 1 1 d . . .
O1W O 1.64303(16) 0.55869(17) 0.03115(15) 0.0421(4) Uani 1 1 d . . .
O3 O 0.57821(17) 0.17921(19) 0.78226(16) 0.0595(6) Uani 1 1 d . . .
O2W O 1.45620(17) 0.65223(16) 0.02302(18) 0.0507(5) Uani 1 1 d . . .
O4 O 0.66094(18) 0.30928(18) 0.88211(17) 0.0614(6) Uani 1 1 d . . .
O3W O 0.95779(15) 0.38911(15) 0.38045(14) 0.0384(4) Uani 1 1 d . . .
O4W O 0.4808(2) 0.0605(3) 0.6165(3) 0.1272(13) Uani 1 1 d G . .
H4WA H 0.4176 0.0496 0.5961 0.191 Uiso 1 1 d G . .
H4WB H 0.5005 0.0912 0.6730 0.191 Uiso 1 1 d G . .
O5W O 1.7847(2) 0.4415(3) 0.0164(3) 0.154(2) Uani 1 1 d G . .
O6W O 1.51739(19) 0.1396(4) 0.4501(3) 0.181(2) Uani 1 1 d G . .
Co1 Co 1.0000 0.5000 0.5000 0.02884(13) Uani 1 2 d S . .
Co2 Co 1.5000 0.5000 0.0000 0.03149(13) Uani 1 2 d S . .
H1WA H 1.648(3) 0.621(3) 0.022(3) 0.059(10) Uiso 1 1 d . . .
H1WB H 1.692(3) 0.533(3) 0.024(3) 0.076(12) Uiso 1 1 d . . .
H2WA H 1.424(3) 0.676(3) 0.059(3) 0.067(10) Uiso 1 1 d . . .
H2WB H 1.482(3) 0.701(4) 0.006(3) 0.066(11) Uiso 1 1 d . . .
H3WA H 0.992(3) 0.370(3) 0.355(3) 0.058(10) Uiso 1 1 d . . .
H3WB H 0.931(3) 0.340(3) 0.402(2) 0.057(10) Uiso 1 1 d . . .
H6 H 1.437(2) 0.316(3) 0.577(2) 0.053(9) Uiso 1 1 d . . .
H7 H 1.371(3) 0.464(3) 0.315(3) 0.063(9) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 N1 1.350(3) . ?
C1 C2 1.369(4) . ?
C2 C3 1.380(4) . ?
C3 C4 1.384(3) . ?
C4 C5 1.396(3) . ?
C4 C6 1.461(3) . ?
C5 N1 1.331(3) . ?
C6 N2 1.258(3) . ?
C7 N3 1.262(4) . ?
C7 C8 1.456(4) . ?
C8 C9 1.389(4) . ?
C8 C12 1.389(3) . ?
C9 C10 1.372(4) . ?
C10 C11 1.380(4) . ?
C11 N4 1.340(3) . ?
C12 N4 1.338(3) . ?
C13 O1 1.249(3) . ?
C13 O2 1.260(3) . ?
C13 C14 1.511(3) . ?
C14 C15 1.379(4) . ?
C14 C19 1.382(4) . ?
C15 C16 1.391(3) . ?
C16 C17 1.374(4) . ?
C17 C18 1.381(4) . ?
C17 C20 1.519(3) . ?
C18 C19 1.379(3) . ?
C20 O3 1.246(3) . ?
C20 O4 1.253(4) . ?
N1 Co1 2.159(2) . ?
N2 N3 1.408(3) . ?
N4 Co2 2.176(2) . ?
O1 Co1 2.0742(15) . ?
O1W Co2 2.0594(19) . ?
O2W Co2 2.0811(19) . ?
O3W Co1 2.1240(18) . ?
Co1 O1 2.0742(15) 3_766 ?
Co1 O3W 2.1240(18) 3_766 ?
Co1 N1 2.159(2) 3_766 ?
Co2 O1W 2.0594(19) 3_865 ?
Co2 O2W 2.0811(19) 3_865 ?
Co2 N4 2.176(2) 3_865 ?

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
N1 C1 C2 122.8(2) . . ?
C1 C2 C3 119.4(2) . . ?
C2 C3 C4 118.9(2) . . ?
C3 C4 C5 118.1(2) . . ?
C3 C4 C6 121.0(2) . . ?
C5 C4 C6 120.9(2) . . ?
N1 C5 C4 123.3(2) . . ?
N2 C6 C4 120.7(2) . . ?
N3 C7 C8 120.8(3) . . ?
C9 C8 C12 117.6(2) . . ?
C9 C8 C7 122.6(2) . . ?
C12 C8 C7 119.8(2) . . ?
C10 C9 C8 119.1(2) . . ?
C9 C10 C11 119.2(2) . . ?
N4 C11 C10 123.1(2) . . ?
N4 C12 C8 123.9(2) . . ?
O1 C13 O2 124.1(2) . . ?
O1 C13 C14 116.8(2) . . ?
O2 C13 C14 119.1(2) . . ?
C15 C14 C19 118.3(2) . . ?
C15 C14 C13 121.5(2) . . ?
C19 C14 C13 120.2(2) . . ?
C14 C15 C16 120.7(3) . . ?
C17 C16 C15 120.8(3) . . ?
C16 C17 C18 118.3(2) . . ?
C16 C17 C20 121.0(2) . . ?
C18 C17 C20 120.7(2) . . ?
C19 C18 C17 121.1(3) . . ?
C18 C19 C14 120.8(3) . . ?
O3 C20 O4 124.3(2) . . ?
O3 C20 C17 119.0(2) . . ?
O4 C20 C17 116.7(3) . . ?
C5 N1 C1 117.5(2) . . ?
C5 N1 Co1 121.55(16) . . ?
C1 N1 Co1 120.69(16) . . ?
C6 N2 N3 112.7(2) . . ?
C7 N3 N2 111.9(2) . . ?
C12 N4 C11 116.9(2) . . ?
C12 N4 Co2 123.41(17) . . ?
C11 N4 Co2 119.65(16) . . ?
C13 O1 Co1 132.62(15) . . ?
O1 Co1 O1 180.00(8) 3_766 . ?
O1 Co1 O3W 86.34(7) 3_766 . ?
O1 Co1 O3W 93.66(7) . . ?
O1 Co1 O3W 93.66(7) 3_766 3_766 ?
O1 Co1 O3W 86.34(7) . 3_766 ?
O3W Co1 O3W 180.0 . 3_766 ?
O1 Co1 N1 91.60(7) 3_766 3_766 ?
O1 Co1 N1 88.40(7) . 3_766 ?
O3W Co1 N1 87.86(8) . 3_766 ?
O3W Co1 N1 92.14(7) 3_766 3_766 ?
O1 Co1 N1 88.40(7) 3_766 . ?
O1 Co1 N1 91.60(7) . . ?
O3W Co1 N1 92.14(7) . . ?
O3W Co1 N1 87.86(8) 3_766 . ?
N1 Co1 N1 180.0 3_766 . ?
O1W Co2 O1W 180.0 . 3_865 ?
O1W Co2 O2W 88.19(9) . . ?
O1W Co2 O2W 91.81(9) 3_865 . ?
O1W Co2 O2W 91.81(9) . 3_865 ?
O1W Co2 O2W 88.19(9) 3_865 3_865 ?
O2W Co2 O2W 180.00(13) . 3_865 ?
O1W Co2 N4 89.80(8) . 3_865 ?
O1W Co2 N4 90.20(8) 3_865 3_865 ?
O2W Co2 N4 85.87(8) . 3_865 ?
O2W Co2 N4 94.13(8) 3_865 3_865 ?
O1W Co2 N4 90.20(8) . . ?
O1W Co2 N4 89.80(8) 3_865 . ?
O2W Co2 N4 94.13(8) . . ?
O2W Co2 N4 85.87(8) 3_865 . ?
N4 Co2 N4 180.000(1) 3_865 . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.794
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.066
_database_code_depnum_ccdc_archive 'CCDC 1000608'
#######################################################################
#
#                 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_DG2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 Co N4 O6'
_chemical_formula_weight         497.37

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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7280(2)
_cell_length_b                   8.6182(2)
_cell_length_c                   10.0558(3)
_cell_angle_alpha                97.3020(10)
_cell_angle_beta                 97.1950(10)
_cell_angle_gamma                92.0550(10)
_cell_volume                     572.99(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    250
_cell_measurement_theta_min      2.06
_cell_measurement_theta_max      27.53

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             257
_exptl_absorpt_coefficient_mu    0.794
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8486
_exptl_absorpt_correction_T_max  0.9461
_exptl_absorpt_process_details   
;
'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL 
SPACE EXPLORATION,
Bruker Analytical X-ray Systems, 1997
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(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            9701
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_av_sigmaI/netI    0.0144
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         27.53
_reflns_number_total             2626
_reflns_number_gt                2532
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'SMART APEX II (Bruker,2010)'
_computing_cell_refinement       'SMART APEX II'
_computing_data_reduction        'SAINT (Bruker,2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3v2 for windows (Farrugia, 1997)'

_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 > 2σ(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)+(0.0498P)²+0.2128P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2626
_refine_ls_number_parameters     159
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0861
_refine_ls_wR_factor_gt          0.0852
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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
Co1 Co 0.5000 0.5000 0.5000 0.02510(11) Uani 1 2 d S . .
O1 O 0.0412(2) 0.37161(17) 0.33486(13) 0.0451(3) Uani 1 1 d . . .
O2 O 0.33873(17) 0.47835(14) 0.30879(11) 0.0334(3) Uani 1 1 d . . .
N1 N 0.6008(2) 0.26528(15) 0.45493(14) 0.0306(3) Uani 1 1 d . . .
N2 N 0.5076(3) 0.0344(2) 0.06792(18) 0.0644(6) Uani 1 1 d . . .
C4 C 0.6574(3) 0.04731(19) 0.29171(19) 0.0373(4) Uani 1 1 d . . .
C9 C 0.0769(2) 0.46829(19) 0.12840(15) 0.0306(3) Uani 1 1 d . . .
C11 C 0.1155(3) 0.5872(2) -0.07068(17) 0.0388(4) Uani 1 1 d . . .
H11 H 0.1937 0.6458 -0.1182 0.047 Uiso 1 1 calc R . .
C5 C 0.5887(2) 0.19546(19) 0.32760(17) 0.0333(3) Uani 1 1 d . . .
H5 H 0.5310 0.2488 0.2589 0.040 Uiso 1 1 calc R . .
C3 C 0.7440(3) -0.0302(2) 0.3954(2) 0.0423(4) Uani 1 1 d . . .
H3 H 0.7931 -0.1289 0.3761 0.051 Uiso 1 1 calc R . .
C8 C 0.1578(2) 0.43562(18) 0.26802(15) 0.0303(3) Uani 1 1 d . . .
C6 C 0.6340(3) -0.0227(2) 0.1478(2) 0.0483(5) Uani 1 1 d . . .
C2 C 0.7566(3) 0.0403(2) 0.5270(2) 0.0418(4) Uani 1 1 d . . .
H2 H 0.8135 -0.0106 0.5976 0.050 Uiso 1 1 calc R . .
C1 C 0.6842(3) 0.1868(2) 0.55327(18) 0.0363(3) Uani 1 1 d . . .
H1 H 0.6933 0.2334 0.6426 0.044 Uiso 1 1 calc R . .
C10 C 0.1909(2) 0.5558(2) 0.05642(17) 0.0385(4) Uani 1 1 d . . .
H10 H 0.3195 0.5937 0.0942 0.046 Uiso 1 1 calc R . .
C7 C 0.7581(8) -0.1553(6) 0.1089(4) 0.159(3) Uani 1 1 d . . .
H7A H 0.7282 -0.1887 0.0135 0.239 Uiso 1 1 calc R . .
H7B H 0.7291 -0.2406 0.1574 0.239 Uiso 1 1 calc R . .
H7C H 0.8976 -0.1225 0.1306 0.239 Uiso 1 1 calc R . .
O1W O 0.24556(18) 0.41216(15) 0.58011(13) 0.0343(3) Uani 1 1 d . . .
H1W H 0.193(4) 0.480(3) 0.623(3) 0.053(7) Uiso 1 1 d . . .
H2W H 0.170(4) 0.391(3) 0.509(3) 0.061(7) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
Co1 O2 2.0690(11) . ?
Co1 O2 2.0690(11) 2_666 ?
Co1 O1W 2.1355(12) 2_666 ?
Co1 O1W 2.1355(12) . ?
Co1 N1 2.1679(13) 2_666 ?
Co1 N1 2.1679(13) . ?
O1 C8 1.252(2) . ?
O2 C8 1.2608(19) . ?
N1 C5 1.335(2) . ?
N1 C1 1.345(2) . ?
N2 C6 1.254(3) . ?
N2 N2 1.408(3) 2_655 ?
C4 C3 1.388(3) . ?
C4 C5 1.393(2) . ?
C4 C6 1.482(3) . ?
C9 C10 1.385(2) . ?
C9 C11 1.392(2) 2_565 ?
C9 C8 1.506(2) . ?
C11 C10 1.378(2) . ?
C11 C9 1.392(2) 2_565 ?
C3 C2 1.375(3) . ?
C6 C7 1.481(3) . ?
C2 C1 1.376(2) . ?

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 Co1 O2 180.0 . 2_666 ?
O2 Co1 O1W 89.22(5) . 2_666 ?
O2 Co1 O1W 90.78(5) 2_666 2_666 ?
O2 Co1 O1W 90.78(5) . . ?
O2 Co1 O1W 89.22(5) 2_666 . ?
O1W Co1 O1W 180.0 2_666 . ?
O2 Co1 N1 90.45(5) . 2_666 ?
O2 Co1 N1 89.55(5) 2_666 2_666 ?
O1W Co1 N1 91.27(5) 2_666 2_666 ?
O1W Co1 N1 88.73(5) . 2_666 ?
O2 Co1 N1 89.55(5) . . ?
O2 Co1 N1 90.45(5) 2_666 . ?
O1W Co1 N1 88.73(5) 2_666 . ?
O1W Co1 N1 91.27(5) . . ?
N1 Co1 N1 180.0 2_666 . ?
C8 O2 Co1 130.86(11) . . ?
C5 N1 C1 117.50(14) . . ?
C5 N1 Co1 121.01(11) . . ?
C1 N1 Co1 121.45(11) . . ?
C6 N2 N2 115.0(2) . 2_655 ?
C3 C4 C5 117.36(16) . . ?
C3 C4 C6 122.49(16) . . ?
C5 C4 C6 120.15(16) . . ?
C10 C9 C11 119.02(15) . 2_565 ?
C10 C9 C8 120.69(14) . . ?
C11 C9 C8 120.29(15) 2_565 . ?
C10 C11 C9 120.41(16) . 2_565 ?
N1 C5 C4 123.76(16) . . ?
C2 C3 C4 119.39(16) . . ?
O1 C8 O2 125.35(14) . . ?
O1 C8 C9 118.15(14) . . ?
O2 C8 C9 116.49(15) . . ?
N2 C6 C7 124.7(2) . . ?
N2 C6 C4 116.98(17) . . ?
C7 C6 C4 118.3(2) . . ?
C3 C2 C1 119.33(17) . . ?
N1 C1 C2 122.64(16) . . ?
C11 C10 C9 120.57(15) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.759
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.052
_database_code_depnum_ccdc_archive 'CCDC 1000609'
#######################################################################
#
#                 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_DG3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H14 N4 O4 Zn'
_chemical_formula_weight         439.72

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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                   19.0040(4)
_cell_length_b                   6.60430(10)
_cell_length_c                   15.8025(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.595(2)
_cell_angle_gamma                90.00
_cell_volume                     1844.13(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    250
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    1.368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8349
_exptl_absorpt_correction_T_max  0.9437
_exptl_absorpt_process_details   
;
'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL 
SPACE EXPLORATION,
Bruker Analytical X-ray Systems, 1997
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(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            14437
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0205
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         27.51
_reflns_number_total             2112
_reflns_number_gt                1897
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'SMART APEX II (Bruker,2010)'
_computing_cell_refinement       'SMART APEX II'
_computing_data_reduction        'SAINT (Bruker,2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3v2 for windows (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2008)'

_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 > 2σ(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)+(0.0505P)²+1.3481P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2112
_refine_ls_number_parameters     132
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0316
_refine_ls_wR_factor_ref         0.0907
_refine_ls_wR_factor_gt          0.0879
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_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
Zn1 Zn 0.5000 0.11640(5) 0.2500 0.03127(13) Uani 1 2 d S . .
O2 O 0.36715(10) 0.1947(3) 0.10041(13) 0.0562(5) Uani 1 1 d . . .
O1 O 0.42085(9) -0.0737(2) 0.18264(11) 0.0447(4) Uani 1 1 d . . .
N1 N 0.44967(10) 0.3102(3) 0.31319(12) 0.0352(4) Uani 1 1 d . . .
N2 N 0.47226(13) 0.9308(3) 0.47446(15) 0.0489(5) Uani 1 1 d . . .
C10 C 0.24628(12) -0.4502(4) 0.02355(16) 0.0402(5) Uani 1 1 d . . .
H10 H 0.2438 -0.5846 0.0398 0.048 Uiso 1 1 calc R . .
C4 C 0.45447(14) 0.6144(3) 0.39764(16) 0.0397(5) Uani 1 1 d . . .
C9 C 0.30330(12) -0.3265(4) 0.07919(16) 0.0400(5) Uani 1 1 d . . .
H9 H 0.3392 -0.3785 0.1322 0.048 Uiso 1 1 calc R . .
C5 C 0.48684(13) 0.4709(3) 0.35912(14) 0.0370(5) Uani 1 1 d . . .
H5 H 0.5372 0.4877 0.3657 0.044 Uiso 1 1 calc R . .
C7 C 0.36851(12) 0.0123(3) 0.11598(15) 0.0386(5) Uani 1 1 d . . .
C8 C 0.30723(12) -0.1246(3) 0.05628(15) 0.0355(5) Uani 1 1 d . . .
C3 C 0.37931(17) 0.5864(4) 0.3883(2) 0.0571(7) Uani 1 1 d . . .
H3 H 0.3555 0.6788 0.4133 0.069 Uiso 1 1 calc R . .
C1 C 0.37745(14) 0.2859(4) 0.30486(18) 0.0491(6) Uani 1 1 d . . .
H1 H 0.3509 0.1742 0.2731 0.059 Uiso 1 1 calc R . .
C6 C 0.50091(15) 0.7806(4) 0.44931(16) 0.0436(5) Uani 1 1 d . . .
H6 H 0.5530 0.7761 0.4642 0.052 Uiso 1 1 calc R . .
C2 C 0.34105(17) 0.4205(5) 0.3417(2) 0.0644(8) Uani 1 1 d . . .
H2 H 0.2909 0.3987 0.3349 0.077 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
Zn1 O1 1.9477(15) . ?
Zn1 O1 1.9477(15) 2_655 ?
Zn1 N1 2.0624(18) . ?
Zn1 N1 2.0624(18) 2_655 ?
O2 C7 1.228(3) . ?
O1 C7 1.285(3) . ?
N1 C5 1.332(3) . ?
N1 C1 1.339(3) . ?
N2 C6 1.264(3) . ?
N2 N2 1.404(4) 5_676 ?
C10 C9 1.383(3) . ?
C10 C8 1.388(3) 7_545 ?
C4 C5 1.387(3) . ?
C4 C3 1.393(4) . ?
C4 C6 1.456(3) . ?
C9 C8 1.390(3) . ?
C7 C8 1.502(3) . ?
C8 C10 1.388(3) 7_545 ?
C3 C2 1.371(4) . ?
C1 C2 1.380(4) . ?

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
O1 Zn1 O1 99.72(10) . 2_655 ?
O1 Zn1 N1 105.20(7) . . ?
O1 Zn1 N1 122.55(7) 2_655 . ?
O1 Zn1 N1 122.55(7) . 2_655 ?
O1 Zn1 N1 105.20(7) 2_655 2_655 ?
N1 Zn1 N1 103.26(10) . 2_655 ?
C7 O1 Zn1 111.85(14) . . ?
C5 N1 C1 117.9(2) . . ?
C5 N1 Zn1 120.72(14) . . ?
C1 N1 Zn1 121.26(16) . . ?
C6 N2 N2 111.9(3) . 5_676 ?
C9 C10 C8 120.5(2) . 7_545 ?
C5 C4 C3 117.8(2) . . ?
C5 C4 C6 119.1(2) . . ?
C3 C4 C6 123.0(2) . . ?
C10 C9 C8 120.4(2) . . ?
N1 C5 C4 123.5(2) . . ?
O2 C7 O1 123.44(19) . . ?
O2 C7 C8 120.7(2) . . ?
O1 C7 C8 115.85(19) . . ?
C10 C8 C9 119.1(2) 7_545 . ?
C10 C8 C7 119.74(19) 7_545 . ?
C9 C8 C7 121.1(2) . . ?
C2 C3 C4 118.9(2) . . ?
N1 C1 C2 122.4(2) . . ?
N2 C6 C4 121.7(2) . . ?
C3 C2 C1 119.5(3) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.064
_database_code_depnum_ccdc_archive 'CCDC 1000610'
#######################################################################
#
#                 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_DG4

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H25 N6 O4 Zn'
_chemical_formula_weight         586.92

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.088(5)
_cell_length_b                   12.001(5)
_cell_length_c                   12.044(5)
_cell_angle_alpha                84.583(5)
_cell_angle_beta                 67.262(5)
_cell_angle_gamma                82.802(5)
_cell_volume                     1332.5(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    250
_cell_measurement_theta_min      1.7
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             606
_exptl_absorpt_coefficient_mu    0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8738
_exptl_absorpt_correction_T_max  0.9728
_exptl_absorpt_process_details   
;
'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL 
SPACE EXPLORATION,
Bruker Analytical X-ray Systems, 1997
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(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            22008
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0440
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         27.54
_reflns_number_total             6082
_reflns_number_gt                4680
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'SMART APEX II (Bruker,2010)'
_computing_cell_refinement       'SMART APEX II'
_computing_data_reduction        'SAINT (Bruker,2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3v2 for windows (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2008)'

_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 > 2σ(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)+(0.0438P)²+0.1365P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6082
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.0947
_refine_ls_wR_factor_gt          0.0882
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

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
C1 C 0.4496(3) 0.1163(2) 0.3274(2) 0.0525(7) Uani 1 1 d . . .
H1 H 0.3693 0.1677 0.3374 0.063 Uiso 1 1 calc R . .
C2 C 0.4440(3) 0.0074(2) 0.3058(3) 0.0636(8) Uani 1 1 d . . .
H2 H 0.3611 -0.0142 0.3008 0.076 Uiso 1 1 calc R . .
C3 C 0.5615(3) -0.0701(2) 0.2914(2) 0.0534(7) Uani 1 1 d . . .
H3 H 0.5588 -0.1441 0.2760 0.064 Uiso 1 1 calc R . .
C4 C 0.6830(2) -0.03700(17) 0.29988(19) 0.0363(5) Uani 1 1 d . . .
C5 C 0.6803(2) 0.07581(17) 0.3196(2) 0.0382(5) Uani 1 1 d . . .
H5 H 0.7630 0.1001 0.3224 0.046 Uiso 1 1 calc R . .
C6 C 0.8131(3) -0.11526(18) 0.2895(2) 0.0392(5) Uani 1 1 d . . .
C7 C 0.8374(3) -0.2235(2) 0.2292(3) 0.0590(7) Uani 1 1 d . . .
H7A H 0.9250 -0.2647 0.2300 0.088 Uiso 1 1 calc R . .
H7B H 0.8451 -0.2080 0.1474 0.088 Uiso 1 1 calc R . .
H7C H 0.7577 -0.2674 0.2715 0.088 Uiso 1 1 calc R . .
C8 C 1.0485(2) -0.17752(16) 0.4169(2) 0.0347(5) Uani 1 1 d . . .
C9 C 0.9510(3) -0.1443(2) 0.5407(2) 0.0513(6) Uani 1 1 d . . .
H9A H 0.8645 -0.1028 0.5377 0.077 Uiso 1 1 calc R . .
H9B H 0.9992 -0.0981 0.5712 0.077 Uiso 1 1 calc R . .
H9C H 0.9265 -0.2105 0.5928 0.077 Uiso 1 1 calc R . .
C10 C 1.1896(2) -0.24317(16) 0.39947(19) 0.0332(5) Uani 1 1 d . . .
C11 C 1.2420(2) -0.25299(17) 0.4903(2) 0.0361(5) Uani 1 1 d . . .
H11 H 1.1855 -0.2189 0.5620 0.043 Uiso 1 1 calc R . .
N4 N 1.36891(19) -0.30839(14) 0.48220(16) 0.0348(4) Uani 1 1 d . . .
C12 C 1.4465(2) -0.36110(17) 0.38082(19) 0.0380(5) Uani 1 1 d . . .
H13 H 1.5342 -0.4012 0.3740 0.046 Uiso 1 1 calc R . .
C14 C 1.2726(3) -0.29865(18) 0.2951(2) 0.0424(6) Uani 1 1 d . . .
H14 H 1.2414 -0.2956 0.2316 0.051 Uiso 1 1 calc R . .
C15 C 0.2917(2) 0.39340(18) 0.3976(2) 0.0411(6) Uani 1 1 d . . .
C16 C 0.1407(2) 0.44817(16) 0.45191(19) 0.0337(5) Uani 1 1 d . . .
C17 C 0.0844(2) 0.48361(17) 0.5682(2) 0.0392(5) Uani 1 1 d . . .
H17 H 0.1406 0.4730 0.6147 0.047 Uiso 1 1 calc R . .
C18 C -0.0548(2) 0.53475(18) 0.6160(2) 0.0404(5) Uani 1 1 d . . .
H18 H -0.0916 0.5581 0.6946 0.048 Uiso 1 1 calc R . .
C23 C 0.4974(3) 0.2672(3) 0.0186(3) 0.0699(8) Uani 1 1 d . . .
H23 H 0.4164 0.3190 0.0350 0.084 Uiso 1 1 calc R . .
C24 C 0.6099(4) 0.2933(3) 0.0442(3) 0.0703(9) Uani 1 1 d . . .
H24 H 0.6061 0.3624 0.0750 0.084 Uiso 1 1 calc R . .
C25 C 0.7295(3) 0.2163(2) 0.0240(2) 0.0642(8) Uani 1 1 d . . .
H25 H 0.8073 0.2332 0.0405 0.077 Uiso 1 1 calc R . .
C26 C 0.7324(3) 0.1139(2) -0.0210(2) 0.0505(6) Uani 1 1 d . . .
C27 C 0.6148(3) 0.0979(2) -0.0467(3) 0.0690(8) Uani 1 1 d . . .
H27 H 0.6168 0.0303 -0.0795 0.083 Uiso 1 1 calc R . .
C28 C 0.8543(3) 0.0255(2) -0.0391(2) 0.0519(6) Uani 1 1 d . . .
C29 C 0.8645(3) -0.0748(2) -0.1077(3) 0.0699(8) Uani 1 1 d . . .
H29A H 0.9484 -0.1242 -0.1111 0.105 Uiso 1 1 calc R . .
H29B H 0.8721 -0.0508 -0.1881 0.105 Uiso 1 1 calc R . .
H29C H 0.7797 -0.1138 -0.0681 0.105 Uiso 1 1 calc R . .
N1 N 0.56696(19) 0.15108(14) 0.33463(16) 0.0375(4) Uani 1 1 d . . .
N2 N 0.8940(2) -0.08419(15) 0.33765(17) 0.0439(5) Uani 1 1 d . . .
N3 N 1.0216(2) -0.15358(15) 0.32198(18) 0.0455(5) Uani 1 1 d . . .
C13 C 1.4018(3) -0.35826(19) 0.2867(2) 0.0447(6) Uani 1 1 d . . .
H13A H 1.4582 -0.3963 0.2176 0.054 Uiso 1 1 calc R . .
N5 N 0.4976(3) 0.1713(2) -0.0286(2) 0.0766(7) Uani 1 1 d . . .
N6 N 0.9436(3) 0.04274(18) 0.0086(2) 0.0599(6) Uani 1 1 d . . .
O1 O 0.36260(16) 0.37414(13) 0.46670(15) 0.0481(4) Uani 1 1 d . . .
O2 O 0.34251(18) 0.36834(15) 0.29152(16) 0.0604(5) Uani 1 1 d . . .
Zn1 Zn 0.56219(3) 0.315153(19) 0.37537(2) 0.03491(10) Uani 1 1 d . . .
O3 O 0.67370(16) 0.42124(13) 0.25149(14) 0.0458(4) Uani 1 1 d . . .
O4 O 0.85164(18) 0.28905(13) 0.24265(14) 0.0501(4) Uani 1 1 d . . .
C20 C 0.9061(2) 0.44343(17) 0.10054(19) 0.0367(5) Uani 1 1 d . . .
C19 C 0.8057(3) 0.37918(19) 0.2061(2) 0.0401(5) Uani 1 1 d . . .
C21 C 0.8555(2) 0.53811(19) 0.0476(2) 0.0465(6) Uani 1 1 d . . .
H21 H 0.7580 0.5640 0.0794 0.056 Uiso 1 1 calc R . .
C22 C 0.9484(3) 0.59387(19) -0.0514(2) 0.0461(6) Uani 1 1 d . . .
H22 H 0.9132 0.6574 -0.0858 0.055 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 N1 1.340(3) . ?
C1 C2 1.368(3) . ?
C2 C3 1.377(3) . ?
C3 C4 1.378(3) . ?
C4 C5 1.392(3) . ?
C4 C6 1.486(3) . ?
C5 N1 1.330(3) . ?
C6 N2 1.274(3) . ?
C6 C7 1.496(3) . ?
C8 N3 1.274(3) . ?
C8 C10 1.487(3) . ?
C8 C9 1.493(3) . ?
C10 C11 1.377(3) . ?
C10 C14 1.389(3) . ?
C11 N4 1.339(2) . ?
N4 C12 1.337(3) . ?
N4 Zn1 2.0769(19) 2_756 ?
C12 C13 1.369(3) . ?
C14 C13 1.378(3) . ?
C15 O2 1.230(3) . ?
C15 O1 1.281(3) . ?
C15 C16 1.497(3) . ?
C16 C17 1.379(3) . ?
C16 C18 1.390(3) 2_566 ?
C17 C18 1.380(3) . ?
C18 C16 1.390(3) 2_566 ?
C23 N5 1.330(4) . ?
C23 C24 1.364(4) . ?
C24 C25 1.380(4) . ?
C25 C26 1.382(4) . ?
C26 C27 1.376(4) . ?
C26 C28 1.481(4) . ?
C27 N5 1.341(4) . ?
C28 N6 1.286(3) . ?
C28 C29 1.494(4) . ?
N1 Zn1 2.0642(19) . ?
N2 N3 1.400(2) . ?
N6 N6 1.398(4) 2_755 ?
O1 Zn1 1.9603(17) . ?
Zn1 O3 1.9533(16) . ?
Zn1 N4 2.0769(19) 2_756 ?
O3 C19 1.283(3) . ?
O4 C19 1.234(3) . ?
C20 C22 1.385(3) 2_765 ?
C20 C21 1.388(3) . ?
C20 C19 1.501(3) . ?
C21 C22 1.375(3) . ?
C22 C20 1.385(3) 2_765 ?

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
N1 C1 C2 122.1(2) . . ?
C1 C2 C3 119.8(2) . . ?
C2 C3 C4 119.4(2) . . ?
C3 C4 C5 117.0(2) . . ?
C3 C4 C6 123.3(2) . . ?
C5 C4 C6 119.7(2) . . ?
N1 C5 C4 124.0(2) . . ?
N2 C6 C4 115.42(19) . . ?
N2 C6 C7 125.2(2) . . ?
C4 C6 C7 119.4(2) . . ?
N3 C8 C10 115.8(2) . . ?
N3 C8 C9 125.2(2) . . ?
C10 C8 C9 119.06(19) . . ?
C11 C10 C14 116.99(19) . . ?
C11 C10 C8 119.93(19) . . ?
C14 C10 C8 123.1(2) . . ?
N4 C11 C10 124.3(2) . . ?
C12 N4 C11 117.43(19) . . ?
C12 N4 Zn1 121.83(14) . 2_756 ?
C11 N4 Zn1 120.72(14) . 2_756 ?
N4 C12 C13 122.5(2) . . ?
C13 C14 C10 119.3(2) . . ?
O2 C15 O1 122.8(2) . . ?
O2 C15 C16 120.3(2) . . ?
O1 C15 C16 116.8(2) . . ?
C17 C16 C18 118.74(19) . 2_566 ?
C17 C16 C15 121.5(2) . . ?
C18 C16 C15 119.8(2) 2_566 . ?
C16 C17 C18 120.4(2) . . ?
C17 C18 C16 120.8(2) . 2_566 ?
N5 C23 C24 123.4(3) . . ?
C23 C24 C25 119.4(3) . . ?
C24 C25 C26 119.3(3) . . ?
C27 C26 C25 116.2(3) . . ?
C27 C26 C28 121.8(3) . . ?
C25 C26 C28 122.0(3) . . ?
N5 C27 C26 125.7(3) . . ?
N6 C28 C26 115.2(2) . . ?
N6 C28 C29 125.3(2) . . ?
C26 C28 C29 119.5(2) . . ?
C5 N1 C1 117.69(19) . . ?
C5 N1 Zn1 122.88(15) . . ?
C1 N1 Zn1 119.38(15) . . ?
C6 N2 N3 116.01(18) . . ?
C8 N3 N2 115.34(19) . . ?
C12 C13 C14 119.5(2) . . ?
C23 N5 C27 115.9(3) . . ?
C28 N6 N6 113.9(3) . 2_755 ?
C15 O1 Zn1 110.47(15) . . ?
O3 Zn1 O1 113.95(7) . . ?
O3 Zn1 N1 119.96(7) . . ?
O1 Zn1 N1 109.71(7) . . ?
O3 Zn1 N4 107.48(7) . 2_756 ?
O1 Zn1 N4 95.94(7) . 2_756 ?
N1 Zn1 N4 106.75(7) . 2_756 ?
C19 O3 Zn1 108.90(14) . . ?
C22 C20 C21 118.8(2) 2_765 . ?
C22 C20 C19 119.9(2) 2_765 . ?
C21 C20 C19 121.3(2) . . ?
O4 C19 O3 123.6(2) . . ?
O4 C19 C20 119.4(2) . . ?
O3 C19 C20 116.9(2) . . ?
C22 C21 C20 120.5(2) . . ?
C21 C22 C20 120.8(2) . 2_765 ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.053
_database_code_depnum_ccdc_archive 'CCDC 1000611'
#######################################################################
#
#                 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_DG5

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 Cd N4 O5'
_chemical_formula_weight         504.77

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           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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                   15.976(5)
_cell_length_b                   6.097(5)
_cell_length_c                   20.824(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 100.578(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1993.9(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    250
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    1.136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8782
_exptl_absorpt_correction_T_max  0.9827
_exptl_absorpt_process_details   
;
'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL 
SPACE EXPLORATION,
Bruker Analytical X-ray Systems, 1997
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(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            15976
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_sigmaI/netI    0.0271
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         27.54
_reflns_number_total             2295
_reflns_number_gt                2088
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'SMART APEX II (Bruker,2010)'
_computing_cell_refinement       'SMART APEX II'
_computing_data_reduction        'SAINT (Bruker,2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3v2 for windows (Farrugia, 1997)'

_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 > 2σ(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)+(0.0252P)²+1.7343P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2295
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0258
_refine_ls_wR_factor_ref         0.0574
_refine_ls_wR_factor_gt          0.0556
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 1.0000 0.17065(3) 0.7500 0.02986(8) Uani 1 2 d S . .
O1 O 1.03059(11) 0.1272(3) 0.63983(8) 0.0420(4) Uani 1 1 d . . .
O2 O 1.02223(12) 0.4591(3) 0.67792(7) 0.0499(5) Uani 1 1 d . . .
N1 N 1.14345(13) 0.1936(3) 0.80544(10) 0.0426(5) Uani 1 1 d . . .
N2 N 1.23208(16) -0.1989(5) 0.96999(11) 0.0626(7) Uani 1 1 d . . .
C5 C 1.17017(16) 0.0711(5) 0.85807(12) 0.0453(6) Uani 1 1 d . . .
H5 H 1.1365 -0.0466 0.8660 0.054 Uiso 1 1 calc R . .
C1 C 1.19291(18) 0.3594(5) 0.79356(14) 0.0540(7) Uani 1 1 d . . .
H1 H 1.1751 0.4461 0.7569 0.065 Uiso 1 1 calc R . .
C4 C 1.24525(15) 0.1089(5) 0.90172(13) 0.0457(6) Uani 1 1 d . . .
C6 C 1.27101(17) -0.0260(5) 0.96057(13) 0.0518(7) Uani 1 1 d . . .
C3 C 1.29476(18) 0.2815(5) 0.88821(15) 0.0620(8) Uani 1 1 d . . .
H3 H 1.3456 0.3132 0.9163 0.074 Uiso 1 1 calc R . .
C2 C 1.26912(19) 0.4070(6) 0.83338(16) 0.0681(9) Uani 1 1 d . . .
H2 H 1.3027 0.5221 0.8234 0.082 Uiso 1 1 calc R . .
C7 C 1.02336(14) 0.3293(4) 0.63146(10) 0.0335(5) Uani 1 1 d . . .
C10 C 0.98769(15) 0.6364(3) 0.55061(11) 0.0332(5) Uani 1 1 d . . .
H10 H 0.9795 0.7285 0.5845 0.040 Uiso 1 1 calc R . .
C9 C 1.02481(14) 0.2857(3) 0.51267(10) 0.0333(5) Uani 1 1 d . . .
H9 H 1.0417 0.1410 0.5211 0.040 Uiso 1 1 calc R . .
C8 C 1.01255(13) 0.4197(4) 0.56359(10) 0.0290(4) Uani 1 1 d . . .
O1W O 1.0000 -0.1931(5) 0.7500 0.0939(16) Uani 1 2 d S . .
H1W H 1.009(3) -0.268(6) 0.7210(19) 0.111(15) Uiso 1 1 d . . .
H6 H 1.3159(18) 0.032(5) 0.9904(15) 0.063(9) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 O1W 2.218(3) . ?
Cd1 N1 2.373(2) . ?
Cd1 N1 2.373(2) 2_756 ?
Cd1 O2 2.381(2) 2_756 ?
Cd1 O2 2.381(2) . ?
Cd1 O1 2.4461(17) 2_756 ?
Cd1 O1 2.4461(17) . ?
Cd1 C7 2.740(2) 2_756 ?
Cd1 C7 2.740(2) . ?
O1 C7 1.247(3) . ?
O2 C7 1.253(3) . ?
N1 C5 1.330(3) . ?
N1 C1 1.334(3) . ?
N2 C6 1.258(4) . ?
N2 N2 1.419(4) 7_747 ?
C5 C4 1.385(3) . ?
C1 C2 1.372(4) . ?
C4 C3 1.376(4) . ?
C4 C6 1.470(4) . ?
C3 C2 1.373(4) . ?
C7 C8 1.497(3) . ?
C10 C9 1.380(3) 5_766 ?
C10 C8 1.392(3) . ?
C9 C10 1.380(3) 5_766 ?
C9 C8 1.381(3) . ?

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
O1W Cd1 N1 93.38(5) . . ?
O1W Cd1 N1 93.38(5) . 2_756 ?
N1 Cd1 N1 173.24(10) . 2_756 ?
O1W Cd1 O2 137.62(5) . 2_756 ?
N1 Cd1 O2 83.81(7) . 2_756 ?
N1 Cd1 O2 91.18(7) 2_756 2_756 ?
O1W Cd1 O2 137.63(5) . . ?
N1 Cd1 O2 91.18(7) . . ?
N1 Cd1 O2 83.81(7) 2_756 . ?
O2 Cd1 O2 84.75(9) 2_756 . ?
O1W Cd1 O1 83.78(4) . 2_756 ?
N1 Cd1 O1 83.77(7) . 2_756 ?
N1 Cd1 O1 96.96(7) 2_756 2_756 ?
O2 Cd1 O1 53.85(6) 2_756 2_756 ?
O2 Cd1 O1 138.58(6) . 2_756 ?
O1W Cd1 O1 83.78(4) . . ?
N1 Cd1 O1 96.96(7) . . ?
N1 Cd1 O1 83.77(7) 2_756 . ?
O2 Cd1 O1 138.58(6) 2_756 . ?
O2 Cd1 O1 53.85(6) . . ?
O1 Cd1 O1 167.57(7) 2_756 . ?
O1W Cd1 C7 110.68(5) . 2_756 ?
N1 Cd1 C7 79.63(7) . 2_756 ?
N1 Cd1 C7 97.95(7) 2_756 2_756 ?
O2 Cd1 C7 27.18(6) 2_756 2_756 ?
O2 Cd1 C7 111.59(8) . 2_756 ?
O1 Cd1 C7 27.07(6) 2_756 2_756 ?
O1 Cd1 C7 165.22(7) . 2_756 ?
O1W Cd1 C7 110.68(5) . . ?
N1 Cd1 C7 97.95(7) . . ?
N1 Cd1 C7 79.63(7) 2_756 . ?
O2 Cd1 C7 111.59(8) 2_756 . ?
O2 Cd1 C7 27.18(6) . . ?
O1 Cd1 C7 165.22(6) 2_756 . ?
O1 Cd1 C7 27.07(6) . . ?
C7 Cd1 C7 138.65(10) 2_756 . ?
C7 O1 Cd1 89.71(14) . . ?
C7 O2 Cd1 92.59(14) . . ?
C5 N1 C1 117.8(2) . . ?
C5 N1 Cd1 120.19(17) . . ?
C1 N1 Cd1 120.44(16) . . ?
C6 N2 N2 112.0(3) . 7_747 ?
N1 C5 C4 123.8(2) . . ?
N1 C1 C2 122.6(3) . . ?
C3 C4 C5 117.0(2) . . ?
C3 C4 C6 121.0(2) . . ?
C5 C4 C6 122.0(3) . . ?
N2 C6 C4 121.9(3) . . ?
C2 C3 C4 120.1(3) . . ?
C1 C2 C3 118.7(3) . . ?
O1 C7 O2 122.0(2) . . ?
O1 C7 C8 119.2(2) . . ?
O2 C7 C8 118.8(2) . . ?
O1 C7 Cd1 63.22(12) . . ?
O2 C7 Cd1 60.23(12) . . ?
C8 C7 Cd1 165.77(16) . . ?
C9 C10 C8 119.9(2) 5_766 . ?
C10 C9 C8 120.9(2) 5_766 . ?
C9 C8 C10 119.2(2) . . ?
C9 C8 C7 119.9(2) . . ?
C10 C8 C7 120.8(2) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.065
_database_code_depnum_ccdc_archive 'CCDC 1000612'
