# Electronic Supplementary Material (ESI) for New Journal of Chemistry
# This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2013


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#                                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. 
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#  fide research purposes only. It may contain copyright material 
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data_icpc01
_database_code_depnum_ccdc_archive 'CCDC 923815'
#TrackingRef 'ICPC01.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H16 Co O8'
_chemical_formula_weight         455.27
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'
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                   7.076(3)
_cell_length_b                   8.7129(11)
_cell_length_c                   15.6143(19)
_cell_angle_alpha                86.398(15)
_cell_angle_beta                 76.694(12)
_cell_angle_gamma                81.384(10)
_cell_volume                     925.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    15
_cell_measurement_theta_min      9.21
_cell_measurement_theta_max      13.91
_exptl_crystal_description       Prism
_exptl_crystal_colour            Brown
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             466
_exptl_absorpt_coefficient_mu    0.977
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.7716
_exptl_absorpt_correction_T_max  0.8918
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'MACH3 Enraf Nonius'
_diffrn_measurement_method       omega
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  120
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4962
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_av_sigmaI/netI    0.2279
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.68
_diffrn_reflns_theta_max         28.44
_reflns_number_total             4663
_reflns_number_gt                2099
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'CAD4-Express Software (Nonius, 1994)'
_computing_cell_refinement       'CAD4-Express Software (Nonius, 1994)'
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0356P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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         4663
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2201
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.1194
_refine_ls_wR_factor_gt          0.0890
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_restrained_S_all      0.968
_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
Co1 Co 0.79989(10) 0.29933(8) 0.23064(4) 0.02850(19) Uani 1 1 d . . .
O1 O 0.7459(4) 0.2191(3) 0.36658(18) 0.0328(8) Uani 1 1 d . . .
O2 O 0.9209(4) 0.0721(3) 0.22262(18) 0.0339(8) Uani 1 1 d . . .
O3 O 0.9716(5) -0.3919(4) 0.3916(2) 0.0481(9) Uani 1 1 d . . .
O4 O 0.5748(4) 0.2156(3) 0.17079(18) 0.0326(8) Uani 1 1 d . . .
O5 O 0.8668(4) 0.3755(3) 0.10551(18) 0.0308(8) Uani 1 1 d . . .
O6 O 0.6756(4) 0.4300(4) -0.16267(18) 0.0351(8) Uani 1 1 d . . .
O7 O 0.5644(5) 0.4675(4) 0.2733(2) 0.0412(9) Uani 1 1 d . . .
H7A H 0.487(6) 0.504(5) 0.238(3) 0.037(14) Uiso 1 1 d . . .
O8 O 1.0152(6) 0.4125(4) 0.2581(3) 0.0373(9) Uani 1 1 d . . .
H8A H 0.994(8) 0.464(7) 0.300(4) 0.08(2) Uiso 1 1 d . . .
H8B H 1.100(7) 0.463(6) 0.221(3) 0.066(19) Uiso 1 1 d . . .
C1 C 0.8017(6) 0.0805(5) 0.3753(3) 0.0259(10) Uani 1 1 d . . .
C2 C 0.8984(6) -0.0092(5) 0.2936(3) 0.0262(10) Uani 1 1 d . . .
C3 C 0.9532(7) -0.1672(5) 0.3021(3) 0.0349(12) Uani 1 1 d . . .
H3 H 1.0107 -0.2226 0.2514 0.042 Uiso 1 1 calc R . .
C4 C 0.9260(7) -0.2488(5) 0.3841(3) 0.0329(11) Uani 1 1 d . . .
C5 C 0.8139(7) -0.2373(6) 0.5478(3) 0.0376(12) Uani 1 1 d . . .
H5 H 0.8547 -0.3435 0.5520 0.045 Uiso 1 1 calc R . .
C6 C 0.7286(7) -0.1537(6) 0.6233(3) 0.0416(13) Uani 1 1 d . . .
H6 H 0.7125 -0.2053 0.6779 0.050 Uiso 1 1 calc R . .
C7 C 0.6672(7) 0.0037(6) 0.6191(3) 0.0398(13) Uani 1 1 d . . .
H7 H 0.6094 0.0581 0.6701 0.048 Uiso 1 1 calc R . .
C8 C 0.6932(6) 0.0794(5) 0.5375(3) 0.0345(11) Uani 1 1 d . . .
H8 H 0.6544 0.1860 0.5339 0.041 Uiso 1 1 calc R . .
C9 C 0.7756(6) -0.0005(5) 0.4620(3) 0.0246(10) Uani 1 1 d . . .
C10 C 0.8377(6) -0.1609(5) 0.4662(3) 0.0293(11) Uani 1 1 d . . .
C11 C 0.5944(6) 0.2569(5) 0.0928(3) 0.0237(10) Uani 1 1 d . . .
C12 C 0.7611(6) 0.3482(5) 0.0535(3) 0.0249(10) Uani 1 1 d . . .
C13 C 0.7851(6) 0.3987(5) -0.0327(3) 0.0287(11) Uani 1 1 d . . .
H13 H 0.8890 0.4533 -0.0569 0.034 Uiso 1 1 calc R . .
C14 C 0.6593(6) 0.3715(5) -0.0859(3) 0.0257(10) Uani 1 1 d . . .
C15 C 0.3831(6) 0.2343(5) -0.1032(3) 0.0318(11) Uani 1 1 d . . .
H15 H 0.4052 0.2670 -0.1621 0.038 Uiso 1 1 calc R . .
C16 C 0.2342(7) 0.1465(5) -0.0693(3) 0.0377(12) Uani 1 1 d . . .
H16 H 0.1581 0.1189 -0.1055 0.045 Uiso 1 1 calc R . .
C17 C 0.1985(7) 0.0997(5) 0.0183(3) 0.0366(12) Uani 1 1 d . . .
H17 H 0.0957 0.0433 0.0415 0.044 Uiso 1 1 calc R . .
C18 C 0.3152(6) 0.1364(5) 0.0718(3) 0.0311(11) Uani 1 1 d . . .
H18 H 0.2914 0.1040 0.1307 0.037 Uiso 1 1 calc R . .
C19 C 0.4679(6) 0.2216(5) 0.0377(3) 0.0241(10) Uani 1 1 d . . .
C20 C 0.4996(6) 0.2739(5) -0.0503(3) 0.0232(10) Uani 1 1 d . . .
C21 C 0.5094(8) 0.5540(6) 0.3504(3) 0.0532(15) Uani 1 1 d . . .
H21A H 0.3906 0.6231 0.3497 0.080 Uiso 1 1 calc R . .
H21B H 0.6117 0.6132 0.3533 0.080 Uiso 1 1 calc R . .
H21C H 0.4885 0.4846 0.4009 0.080 Uiso 1 1 calc R . .
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
Co1 0.0363(4) 0.0264(4) 0.0249(3) 0.0030(3) -0.0104(3) -0.0070(3)
O1 0.044(2) 0.0235(18) 0.0292(18) 0.0017(15) -0.0091(15) -0.0001(16)
O2 0.047(2) 0.0301(18) 0.0233(16) 0.0018(14) -0.0072(14) -0.0043(16)
O3 0.081(3) 0.0225(19) 0.039(2) 0.0020(15) -0.0188(19) 0.0046(18)
O4 0.041(2) 0.036(2) 0.0238(17) 0.0026(15) -0.0083(15) -0.0130(16)
O5 0.0369(19) 0.0323(19) 0.0276(17) 0.0032(14) -0.0118(15) -0.0135(16)
O6 0.0379(19) 0.043(2) 0.0269(17) 0.0118(15) -0.0107(14) -0.0145(16)
O7 0.047(2) 0.040(2) 0.037(2) -0.0095(16) -0.0210(18) 0.0130(18)
O8 0.045(2) 0.041(2) 0.030(2) -0.0003(18) -0.0085(17) -0.0224(19)
C1 0.027(3) 0.025(3) 0.029(2) 0.002(2) -0.014(2) -0.005(2)
C2 0.028(3) 0.026(3) 0.026(2) 0.001(2) -0.009(2) -0.007(2)
C3 0.049(3) 0.030(3) 0.025(2) -0.004(2) -0.007(2) -0.006(2)
C4 0.037(3) 0.029(3) 0.038(3) 0.000(2) -0.017(2) -0.007(2)
C5 0.042(3) 0.032(3) 0.041(3) 0.013(2) -0.016(2) -0.010(2)
C6 0.047(3) 0.049(3) 0.030(3) 0.012(3) -0.008(2) -0.016(3)
C7 0.044(3) 0.047(3) 0.026(3) -0.007(2) -0.003(2) -0.005(3)
C8 0.045(3) 0.032(3) 0.028(3) -0.001(2) -0.011(2) -0.007(2)
C9 0.029(3) 0.021(2) 0.026(2) -0.0015(19) -0.0091(19) -0.008(2)
C10 0.033(3) 0.030(3) 0.027(2) 0.002(2) -0.009(2) -0.009(2)
C11 0.027(2) 0.022(2) 0.021(2) -0.0029(19) -0.0043(19) -0.002(2)
C12 0.025(2) 0.023(2) 0.029(2) -0.001(2) -0.010(2) -0.006(2)
C13 0.027(3) 0.034(3) 0.030(2) 0.007(2) -0.010(2) -0.015(2)
C14 0.029(3) 0.022(2) 0.024(2) 0.0047(19) -0.004(2) -0.002(2)
C15 0.036(3) 0.032(3) 0.031(3) 0.000(2) -0.013(2) -0.011(2)
C16 0.037(3) 0.036(3) 0.046(3) -0.006(2) -0.019(2) -0.008(2)
C17 0.031(3) 0.036(3) 0.048(3) 0.000(2) -0.012(2) -0.013(2)
C18 0.033(3) 0.033(3) 0.028(2) 0.000(2) -0.005(2) -0.009(2)
C19 0.024(2) 0.024(2) 0.026(2) -0.0033(19) -0.0060(19) -0.006(2)
C20 0.027(2) 0.016(2) 0.027(2) -0.0021(18) -0.0069(19) -0.0032(19)
C21 0.056(4) 0.056(4) 0.048(3) -0.020(3) -0.011(3) 0.002(3)
_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
Co1 O5 1.997(3) . ?
Co1 O2 2.035(3) . ?
Co1 O7 2.061(3) . ?
Co1 O8 2.069(3) . ?
Co1 O1 2.159(3) . ?
Co1 O4 2.250(3) . ?
O1 C1 1.222(5) . ?
O2 C2 1.269(4) . ?
O3 C4 1.246(5) . ?
O4 C11 1.231(4) . ?
O5 C12 1.278(4) . ?
O6 C14 1.261(4) . ?
O7 C21 1.407(5) . ?
C1 C9 1.473(5) . ?
C1 C2 1.506(6) . ?
C2 C3 1.380(6) . ?
C3 C4 1.412(6) . ?
C4 C10 1.494(6) . ?
C5 C10 1.387(5) . ?
C5 C6 1.390(6) . ?
C6 C7 1.378(6) . ?
C7 C8 1.383(6) . ?
C8 C9 1.372(6) . ?
C9 C10 1.402(6) . ?
C11 C19 1.451(5) . ?
C11 C12 1.512(6) . ?
C12 C13 1.369(5) . ?
C13 C14 1.402(5) . ?
C14 C20 1.499(6) . ?
C15 C16 1.381(6) . ?
C15 C20 1.385(5) . ?
C16 C17 1.379(6) . ?
C17 C18 1.382(6) . ?
C18 C19 1.388(5) . ?
C19 C20 1.398(5) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 Co1 O2 102.51(12) . . ?
O5 Co1 O7 97.10(13) . . ?
O2 Co1 O7 150.31(13) . . ?
O5 Co1 O8 89.74(14) . . ?
O2 Co1 O8 104.40(14) . . ?
O7 Co1 O8 97.70(15) . . ?
O5 Co1 O1 176.37(13) . . ?
O2 Co1 O1 77.03(12) . . ?
O7 Co1 O1 84.72(12) . . ?
O8 Co1 O1 86.89(13) . . ?
O5 Co1 O4 76.59(11) . . ?
O2 Co1 O4 82.97(11) . . ?
O7 Co1 O4 80.14(13) . . ?
O8 Co1 O4 165.71(12) . . ?
O1 Co1 O4 106.86(11) . . ?
C1 O1 Co1 112.8(3) . . ?
C2 O2 Co1 117.1(3) . . ?
C11 O4 Co1 111.3(3) . . ?
C12 O5 Co1 118.7(3) . . ?
C21 O7 Co1 131.0(3) . . ?
O1 C1 C9 122.4(4) . . ?
O1 C1 C2 118.1(4) . . ?
C9 C1 C2 119.6(4) . . ?
O2 C2 C3 126.6(4) . . ?
O2 C2 C1 114.7(4) . . ?
C3 C2 C1 118.7(4) . . ?
C2 C3 C4 123.0(4) . . ?
O3 C4 C3 123.1(4) . . ?
O3 C4 C10 117.8(4) . . ?
C3 C4 C10 119.1(4) . . ?
C10 C5 C6 119.4(5) . . ?
C7 C6 C5 121.6(4) . . ?
C6 C7 C8 118.7(4) . . ?
C9 C8 C7 120.9(4) . . ?
C8 C9 C10 120.4(4) . . ?
C8 C9 C1 120.7(4) . . ?
C10 C9 C1 118.9(4) . . ?
C5 C10 C9 119.0(4) . . ?
C5 C10 C4 120.3(4) . . ?
C9 C10 C4 120.7(4) . . ?
O4 C11 C19 123.5(4) . . ?
O4 C11 C12 117.3(4) . . ?
C19 C11 C12 119.3(4) . . ?
O5 C12 C13 125.0(4) . . ?
O5 C12 C11 116.1(3) . . ?
C13 C12 C11 118.9(4) . . ?
C12 C13 C14 122.7(4) . . ?
O6 C14 C13 121.1(4) . . ?
O6 C14 C20 119.2(4) . . ?
C13 C14 C20 119.6(4) . . ?
C16 C15 C20 120.5(4) . . ?
C17 C16 C15 120.1(4) . . ?
C16 C17 C18 120.1(4) . . ?
C17 C18 C19 120.2(4) . . ?
C18 C19 C20 119.7(4) . . ?
C18 C19 C11 120.5(4) . . ?
C20 C19 C11 119.8(4) . . ?
C15 C20 C19 119.4(4) . . ?
C15 C20 C14 121.0(4) . . ?
C19 C20 C14 119.6(4) . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H7A O6 0.88(4) 1.84(4) 2.714(4) 177(4) 2_665
O8 H8A O3 0.79(5) 1.92(6) 2.709(5) 171(6) 1_565
O8 H8B O6 0.88(5) 1.97(5) 2.834(5) 165(5) 2_765
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.44
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.735
_refine_diff_density_rms         0.104


data_isa0310
_database_code_depnum_ccdc_archive 'CCDC 923816'
#TrackingRef 'ISA0310.CIF'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H18 Co N2 O6'
_chemical_formula_weight         561.39
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'
O O 0.0106 0.0060 '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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'A b a 2'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z+1/2'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z+1'
'x+1/2, -y+1/2, z+1'
_cell_length_a                   19.554(4)
_cell_length_b                   14.761(3)
_cell_length_c                   8.3825(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2419.5(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    868
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      17.84
_exptl_crystal_description       Block
_exptl_crystal_colour            'Dark red'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1148
_exptl_absorpt_coefficient_mu    0.761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8268
_exptl_absorpt_correction_T_max  0.8880
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Smart-CCD-1000 BRUKER'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6642
_diffrn_reflns_av_R_equivalents  0.1024
_diffrn_reflns_av_sigmaI/netI    0.1463
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         28.01
_reflns_number_total             2095
_reflns_number_gt                1049
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0220P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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   0.00(4)
_refine_ls_number_reflns         2095
_refine_ls_number_parameters     177
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1456
_refine_ls_R_factor_gt           0.0618
_refine_ls_wR_factor_ref         0.1084
_refine_ls_wR_factor_gt          0.0944
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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
Co1 Co 0.5000 0.5000 0.3253(2) 0.0448(3) Uani 1 2 d S . .
O1 O 0.4099(2) 0.5831(3) 0.3131(8) 0.0494(11) Uani 1 1 d . . .
O2 O 0.4389(2) 0.4277(3) 0.1798(6) 0.0571(15) Uani 1 1 d . . .
O3 O 0.2090(3) 0.4076(4) 0.0157(9) 0.085(2) Uani 1 1 d . . .
N1 N 0.4730(3) 0.4201(5) 0.5242(7) 0.0522(18) Uani 1 1 d . . .
C1 C 0.3620(3) 0.5446(5) 0.2475(8) 0.0393(17) Uani 1 1 d . . .
C2 C 0.3758(4) 0.4537(5) 0.1669(9) 0.0483(19) Uani 1 1 d . . .
C3 C 0.3239(4) 0.4161(5) 0.0901(10) 0.058(3) Uani 1 1 d . . .
H3 H 0.3336 0.3632 0.0342 0.070 Uiso 1 1 calc R . .
C4 C 0.2564(5) 0.4462(5) 0.0829(15) 0.062(2) Uani 1 1 d . . .
C5 C 0.1750(4) 0.5704(6) 0.1702(10) 0.064(2) Uani 1 1 d . . .
H5 H 0.1395 0.5388 0.1218 0.077 Uiso 1 1 calc R . .
C6 C 0.1620(4) 0.6532(6) 0.2431(10) 0.077(3) Uani 1 1 d . . .
H6 H 0.1178 0.6763 0.2443 0.093 Uiso 1 1 calc R . .
C7 C 0.2136(4) 0.7004(4) 0.3124(15) 0.065(2) Uani 1 1 d . . .
H7 H 0.2045 0.7560 0.3600 0.078 Uiso 1 1 calc R . .
C8 C 0.2780(3) 0.6677(4) 0.3132(13) 0.0534(18) Uani 1 1 d . . .
H8 H 0.3130 0.7007 0.3610 0.064 Uiso 1 1 calc R . .
C9 C 0.2923(4) 0.5832(5) 0.2413(8) 0.050(2) Uani 1 1 d . . .
C10 C 0.2397(4) 0.5352(5) 0.1694(11) 0.060(2) Uani 1 1 d . . .
C11 C 0.4849(4) 0.4528(5) 0.6710(10) 0.068(3) Uani 1 1 d . . .
C12 C 0.4750(4) 0.4049(8) 0.8073(16) 0.101(3) Uani 1 1 d . . .
H12 H 0.4853 0.4290 0.9070 0.122 Uiso 1 1 calc R . .
C13 C 0.4491(6) 0.3184(11) 0.7903(19) 0.129(6) Uani 1 1 d . . .
H13 H 0.4414 0.2830 0.8803 0.154 Uiso 1 1 calc R . .
C14 C 0.4346(6) 0.2847(8) 0.6437(18) 0.116(5) Uani 1 1 d . . .
H14 H 0.4166 0.2266 0.6343 0.140 Uiso 1 1 calc R . .
C15 C 0.4463(4) 0.3357(6) 0.5079(11) 0.080(3) Uani 1 1 d . . .
H15 H 0.4361 0.3126 0.4075 0.096 Uiso 1 1 calc R . .
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
Co1 0.0548(6) 0.0347(6) 0.0449(6) 0.000 0.000 0.0010(8)
O1 0.050(2) 0.040(2) 0.058(3) -0.011(4) -0.008(4) -0.004(2)
O2 0.067(4) 0.036(3) 0.068(4) -0.016(3) -0.013(3) 0.014(3)
O3 0.076(5) 0.053(4) 0.125(6) -0.031(4) -0.026(4) -0.014(3)
N1 0.056(4) 0.058(5) 0.042(5) 0.007(3) 0.016(3) 0.012(3)
C1 0.047(4) 0.034(4) 0.037(4) 0.002(3) -0.007(3) -0.003(4)
C2 0.068(5) 0.040(4) 0.037(4) -0.009(4) 0.006(5) 0.007(4)
C3 0.073(6) 0.037(5) 0.065(6) -0.015(4) -0.008(5) -0.011(5)
C4 0.059(6) 0.042(5) 0.085(6) 0.004(6) -0.011(5) -0.020(6)
C5 0.045(5) 0.072(6) 0.076(6) -0.012(5) 0.006(5) -0.014(5)
C6 0.054(5) 0.070(6) 0.108(8) -0.004(5) 0.010(5) 0.018(5)
C7 0.059(5) 0.041(4) 0.095(6) -0.008(6) -0.021(8) 0.009(4)
C8 0.053(4) 0.039(4) 0.069(5) 0.018(6) -0.016(6) -0.001(3)
C9 0.054(5) 0.044(5) 0.053(5) 0.006(4) -0.010(4) -0.009(4)
C10 0.050(5) 0.049(5) 0.080(6) 0.008(4) -0.004(5) -0.006(4)
C11 0.075(7) 0.087(6) 0.040(5) 0.026(4) 0.009(5) 0.033(5)
C12 0.090(8) 0.154(10) 0.060(7) 0.035(10) 0.007(8) 0.041(7)
C13 0.090(8) 0.150(13) 0.145(14) 0.105(12) 0.026(12) 0.043(9)
C14 0.108(9) 0.070(8) 0.170(13) 0.059(9) 0.048(11) 0.000(6)
C15 0.086(6) 0.060(7) 0.094(7) 0.017(5) 0.029(6) -0.007(6)
_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
Co1 O2 2.013(5) . ?
Co1 O2 2.013(5) 2_665 ?
Co1 N1 2.110(6) 2_665 ?
Co1 N1 2.110(6) . ?
Co1 O1 2.150(4) 2_665 ?
Co1 O1 2.150(4) . ?
O1 C1 1.226(7) . ?
O2 C2 1.298(8) . ?
O3 C4 1.226(10) . ?
N1 C11 1.343(9) . ?
N1 C15 1.358(9) . ?
C1 C9 1.477(10) . ?
C1 C2 1.526(9) . ?
C2 C3 1.324(9) . ?
C3 C4 1.393(11) . ?
C4 C10 1.535(11) . ?
C5 C10 1.367(10) . ?
C5 C6 1.389(11) . ?
C6 C7 1.356(10) . ?
C7 C8 1.349(7) . ?
C8 C9 1.412(9) . ?
C9 C10 1.387(9) . ?
C11 C12 1.357(13) . ?
C11 C11 1.513(16) 2_665 ?
C12 C13 1.381(15) . ?
C13 C14 1.356(18) . ?
C14 C15 1.383(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
O2 Co1 O2 105.5(3) . 2_665 ?
O2 Co1 N1 157.46(19) . 2_665 ?
O2 Co1 N1 91.9(3) 2_665 2_665 ?
O2 Co1 N1 91.9(3) . . ?
O2 Co1 N1 157.46(19) 2_665 . ?
N1 Co1 N1 75.5(4) 2_665 . ?
O2 Co1 O1 98.9(2) . 2_665 ?
O2 Co1 O1 77.71(19) 2_665 2_665 ?
N1 Co1 O1 98.7(2) 2_665 2_665 ?
N1 Co1 O1 85.6(2) . 2_665 ?
O2 Co1 O1 77.71(19) . . ?
O2 Co1 O1 98.9(2) 2_665 . ?
N1 Co1 O1 85.6(2) 2_665 . ?
N1 Co1 O1 98.7(2) . . ?
O1 Co1 O1 174.6(4) 2_665 . ?
C1 O1 Co1 112.6(4) . . ?
C2 O2 Co1 117.3(4) . . ?
C11 N1 C15 119.3(7) . . ?
C11 N1 Co1 118.7(5) . . ?
C15 N1 Co1 122.0(6) . . ?
O1 C1 C9 122.8(6) . . ?
O1 C1 C2 118.1(6) . . ?
C9 C1 C2 119.1(7) . . ?
O2 C2 C3 130.2(7) . . ?
O2 C2 C1 113.1(6) . . ?
C3 C2 C1 116.7(7) . . ?
C2 C3 C4 127.8(9) . . ?
O3 C4 C3 126.0(9) . . ?
O3 C4 C10 117.0(8) . . ?
C3 C4 C10 117.0(8) . . ?
C10 C5 C6 120.4(8) . . ?
C7 C6 C5 120.3(8) . . ?
C8 C7 C6 120.8(8) . . ?
C7 C8 C9 119.9(8) . . ?
C10 C9 C8 119.3(7) . . ?
C10 C9 C1 120.1(7) . . ?
C8 C9 C1 120.5(6) . . ?
C5 C10 C9 119.3(8) . . ?
C5 C10 C4 121.7(8) . . ?
C9 C10 C4 119.0(7) . . ?
N1 C11 C12 124.0(9) . . ?
N1 C11 C11 113.5(4) . 2_665 ?
C12 C11 C11 122.4(7) . 2_665 ?
C11 C12 C13 116.6(14) . . ?
C14 C13 C12 120.6(15) . . ?
C13 C14 C15 120.8(13) . . ?
N1 C15 C14 118.7(10) . . ?
_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        28.01
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.751
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.072


data_cdl2
_database_code_depnum_ccdc_archive 'CCDC 923817'
#TrackingRef 'cdl2.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H18 Cd N2 O6'
_chemical_formula_weight         614.86
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P b n n'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x, -y+1/2, -z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x, y-1/2, z'
'x-1/2, -y, z-1/2'
_cell_length_a                   9.2002(3)
_cell_length_b                   16.3387(5)
_cell_length_c                   16.4478(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2472.42(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_description       Plate
_exptl_crystal_colour            'Dark red'
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_absorpt_coefficient_mu    0.934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6525
_exptl_absorpt_correction_T_max  0.9124
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Smart-CCD-1000 BRUKER'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17071
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         28.27
_reflns_number_total             3063
_reflns_number_gt                2485
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'BRUKER Smart'
_computing_cell_refinement       'BRUKER Smart'
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0379P)^2^+0.7092P] where P=(Fo^2^+2Fc^2^)/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_number_reflns         3063
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0741
_refine_ls_wR_factor_gt          0.0698
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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 0.2500 0.025431(11) 0.7500 0.04115(8) Uani 1 2 d S . .
O1 O 0.47996(15) -0.02048(9) 0.69692(9) 0.0518(4) Uani 1 1 d . . .
O2 O 0.21011(14) -0.04748(9) 0.63952(9) 0.0471(3) Uani 1 1 d . . .
O3 O 0.4227(2) -0.17956(15) 0.41579(11) 0.0878(6) Uani 1 1 d . . .
N1 N 0.38797(16) 0.14058(9) 0.77713(10) 0.0386(3) Uani 1 1 d . . .
C1 C 0.46849(18) -0.05334(10) 0.63006(12) 0.0373(4) Uani 1 1 d . . .
C2 C 0.31873(18) -0.07278(11) 0.59729(12) 0.0393(4) Uani 1 1 d . . .
C3 C 0.3100(2) -0.11682(14) 0.52740(13) 0.0517(5) Uani 1 1 d . . .
H3 H 0.2181 -0.1313 0.5086 0.062 Uiso 1 1 calc R . .
C4 C 0.4337(2) -0.14230(15) 0.48079(13) 0.0546(5) Uani 1 1 d . . .
C5 C 0.7049(3) -0.14298(19) 0.46832(15) 0.0660(7) Uani 1 1 d . . .
H5 H 0.6961 -0.1736 0.4209 0.079 Uiso 1 1 calc R . .
C6 C 0.8410(3) -0.12017(19) 0.49586(16) 0.0733(7) Uani 1 1 d . . .
H6 H 0.9230 -0.1359 0.4667 0.088 Uiso 1 1 calc R . .
C7 C 0.8569(2) -0.07479(18) 0.56544(15) 0.0648(6) Uani 1 1 d . . .
H7 H 0.9489 -0.0589 0.5827 0.078 Uiso 1 1 calc R . .
C8 C 0.7354(2) -0.05289(16) 0.60967(15) 0.0514(5) Uani 1 1 d . . .
H8 H 0.7455 -0.0227 0.6572 0.062 Uiso 1 1 calc R . .
C9 C 0.59786(19) -0.07596(12) 0.58315(11) 0.0400(4) Uani 1 1 d . . .
C10 C 0.5819(2) -0.12046(13) 0.51106(12) 0.0465(4) Uani 1 1 d . . .
C11 C 0.32754(19) 0.21375(11) 0.76348(10) 0.0356(4) Uani 1 1 d . . .
C12 C 0.4063(3) 0.28493(13) 0.77428(15) 0.0552(5) Uani 1 1 d . . .
H12 H 0.3645 0.3354 0.7628 0.066 Uiso 1 1 calc R . .
C13 C 0.5476(3) 0.28041(15) 0.80227(16) 0.0636(6) Uani 1 1 d . . .
H13 H 0.6010 0.3280 0.8107 0.076 Uiso 1 1 calc R . .
C14 C 0.6081(2) 0.20586(14) 0.81739(13) 0.0537(5) Uani 1 1 d . . .
H14 H 0.7028 0.2016 0.8368 0.064 Uiso 1 1 calc R . .
C15 C 0.5259(2) 0.13721(13) 0.80324(13) 0.0488(5) Uani 1 1 d . . .
H15 H 0.5676 0.0862 0.8122 0.059 Uiso 1 1 calc R . .
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 0.03046(11) 0.02966(11) 0.06333(15) 0.000 0.00548(8) 0.000
O1 0.0333(7) 0.0600(9) 0.0622(9) -0.0176(7) 0.0007(6) 0.0003(6)
O2 0.0279(6) 0.0475(7) 0.0659(9) -0.0052(7) 0.0022(6) -0.0056(6)
O3 0.0652(11) 0.1348(18) 0.0634(10) -0.0399(12) -0.0026(9) -0.0066(12)
N1 0.0311(7) 0.0355(8) 0.0491(8) 0.0016(7) -0.0007(6) -0.0021(6)
C1 0.0302(8) 0.0310(8) 0.0506(10) 0.0030(7) 0.0011(7) -0.0009(6)
C2 0.0292(8) 0.0353(9) 0.0533(10) 0.0064(8) 0.0015(8) -0.0040(7)
C3 0.0349(9) 0.0611(13) 0.0592(12) -0.0058(10) -0.0050(9) -0.0072(9)
C4 0.0481(11) 0.0679(14) 0.0478(11) -0.0066(10) -0.0015(9) -0.0055(10)
C5 0.0517(12) 0.097(2) 0.0498(12) -0.0084(12) 0.0113(10) 0.0052(13)
C6 0.0418(12) 0.114(2) 0.0642(15) 0.0026(15) 0.0165(11) 0.0099(13)
C7 0.0320(9) 0.0959(18) 0.0664(14) 0.0076(14) 0.0041(10) 0.0011(12)
C8 0.0330(10) 0.0646(13) 0.0565(12) 0.0016(11) 0.0003(8) -0.0035(9)
C9 0.0302(8) 0.0434(10) 0.0463(10) 0.0056(8) 0.0016(7) -0.0009(7)
C10 0.0389(10) 0.0572(12) 0.0435(10) 0.0043(9) 0.0037(8) -0.0011(9)
C11 0.0352(9) 0.0336(8) 0.0379(9) -0.0012(7) 0.0020(7) -0.0026(7)
C12 0.0551(13) 0.0355(10) 0.0750(14) -0.0034(10) -0.0053(11) -0.0076(9)
C13 0.0540(13) 0.0565(13) 0.0802(17) -0.0083(12) -0.0076(12) -0.0211(11)
C14 0.0356(9) 0.0705(14) 0.0551(12) -0.0050(11) -0.0039(9) -0.0115(10)
C15 0.0342(9) 0.0500(11) 0.0624(12) 0.0039(9) -0.0033(9) 0.0023(8)
_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 O2 2.2036(15) . ?
Cd1 O2 2.2036(15) 4_556 ?
Cd1 N1 2.3130(15) . ?
Cd1 N1 2.3130(15) 4_556 ?
Cd1 O1 2.4085(14) 4_556 ?
Cd1 O1 2.4085(14) . ?
O1 C1 1.228(2) . ?
O2 C2 1.285(2) . ?
O3 C4 1.235(3) . ?
N1 C11 1.337(2) . ?
N1 C15 1.341(2) . ?
C1 C9 1.466(2) . ?
C1 C2 1.513(2) . ?
C2 C3 1.359(3) . ?
C3 C4 1.435(3) . ?
C4 C10 1.494(3) . ?
C5 C10 1.382(3) . ?
C5 C6 1.383(4) . ?
C6 C7 1.372(4) . ?
C7 C8 1.381(3) . ?
C8 C9 1.390(3) . ?
C9 C10 1.399(3) . ?
C11 C12 1.382(3) . ?
C11 C11 1.494(4) 4_556 ?
C12 C13 1.381(3) . ?
C13 C14 1.362(3) . ?
C14 C15 1.373(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
O2 Cd1 O2 114.55(8) . 4_556 ?
O2 Cd1 N1 133.64(5) . . ?
O2 Cd1 N1 100.91(6) 4_556 . ?
O2 Cd1 N1 100.91(6) . 4_556 ?
O2 Cd1 N1 133.64(5) 4_556 4_556 ?
N1 Cd1 N1 71.14(8) . 4_556 ?
O2 Cd1 O1 89.10(5) . 4_556 ?
O2 Cd1 O1 71.28(5) 4_556 4_556 ?
N1 Cd1 O1 131.72(5) . 4_556 ?
N1 Cd1 O1 80.86(5) 4_556 4_556 ?
O2 Cd1 O1 71.28(5) . . ?
O2 Cd1 O1 89.10(5) 4_556 . ?
N1 Cd1 O1 80.86(5) . . ?
N1 Cd1 O1 131.72(5) 4_556 . ?
O1 Cd1 O1 143.71(7) 4_556 . ?
C1 O1 Cd1 112.65(12) . . ?
C2 O2 Cd1 119.35(12) . . ?
C11 N1 C15 118.94(16) . . ?
C11 N1 Cd1 117.81(12) . . ?
C15 N1 Cd1 123.21(13) . . ?
O1 C1 C9 120.77(16) . . ?
O1 C1 C2 119.27(16) . . ?
C9 C1 C2 119.93(16) . . ?
O2 C2 C3 125.55(17) . . ?
O2 C2 C1 116.61(17) . . ?
C3 C2 C1 117.82(17) . . ?
C2 C3 C4 123.96(18) . . ?
O3 C4 C3 122.7(2) . . ?
O3 C4 C10 118.8(2) . . ?
C3 C4 C10 118.48(19) . . ?
C10 C5 C6 120.2(2) . . ?
C7 C6 C5 121.1(2) . . ?
C6 C7 C8 119.5(2) . . ?
C7 C8 C9 120.1(2) . . ?
C8 C9 C10 120.17(18) . . ?
C8 C9 C1 120.36(18) . . ?
C10 C9 C1 119.46(16) . . ?
C5 C10 C9 118.91(19) . . ?
C5 C10 C4 120.9(2) . . ?
C9 C10 C4 120.17(18) . . ?
N1 C11 C12 120.85(18) . . ?
N1 C11 C11 116.54(10) . 4_556 ?
C12 C11 C11 122.61(12) . 4_556 ?
C13 C12 C11 119.4(2) . . ?
C14 C13 C12 119.6(2) . . ?
C13 C14 C15 118.29(19) . . ?
N1 C15 C14 122.84(19) . . ?
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.27
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.727
_refine_diff_density_rms         0.061


data_Compound1
_database_code_depnum_ccdc_archive 'CCDC 923818'
#TrackingRef 'Compound 1.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H18 Co O9'
_chemical_formula_weight         473.28
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'
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           Tetragonal
_symmetry_space_group_name_H-M   'P 4(2)/n'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-y, x+1/2, z+1/2'
'y+1/2, -x, z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'y, -x-1/2, -z-1/2'
'-y-1/2, x, -z-1/2'
_cell_length_a                   13.6277(3)
_cell_length_b                   13.6277(3)
_cell_length_c                   21.4357(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3980.91(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_description       Plate
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1944
_exptl_absorpt_coefficient_mu    0.915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8381
_exptl_absorpt_correction_T_max  0.9731
_exptl_absorpt_process_details   
;
Sheldrick, G.M. SADABS: Program for absorption correction
using area detector data. University of G ttingen, Germany, 1996.
;
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Smart-CCD-1000 BRUKER'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23149
_diffrn_reflns_av_R_equivalents  0.1855
_diffrn_reflns_av_sigmaI/netI    0.1259
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         26.36
_reflns_number_total             4055
_reflns_number_gt                1971
_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    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
12 least-square restraints (DFIX/DANG) were used to model the water
molecules coordinated to the cobalt atom.
The Uij components of the carbon atom of the methanol solvent molecule
(C1S) were restrained to approximate to isotropic behavior (ISOR). This
restraint was necessary to prevent the atom to become non-positive-
definite.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1040P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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         4055
_refine_ls_number_parameters     296
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1682
_refine_ls_R_factor_gt           0.0748
_refine_ls_wR_factor_ref         0.2138
_refine_ls_wR_factor_gt          0.1693
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_restrained_S_all      0.975
_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 0.88980(6) 0.11684(6) 0.66284(3) 0.0341(3) Uani 1 1 d . . .
O1 O 0.9128(3) 0.1250(3) 0.7636(2) 0.0515(12) Uani 1 1 d . . .
O2 O 0.7495(3) 0.1254(3) 0.69726(19) 0.0507(12) Uani 1 1 d . . .
O3 O 0.5714(4) 0.0973(4) 0.8829(2) 0.0630(14) Uani 1 1 d . . .
O4 O 0.8812(3) -0.0505(3) 0.6767(2) 0.0493(12) Uani 1 1 d . . .
O5 O 0.8631(4) 0.0657(3) 0.5772(2) 0.0564(13) Uani 1 1 d . . .
O6 O 0.8853(4) -0.2112(4) 0.4493(2) 0.0674(15) Uani 1 1 d . . .
O7 O 1.0415(4) 0.1084(4) 0.6539(2) 0.0565(13) Uani 1 1 d D . .
O8 O 0.8945(4) 0.2644(4) 0.6456(3) 0.0647(15) Uani 1 1 d D . .
C1 C 0.8347(5) 0.1270(4) 0.7929(3) 0.0406(15) Uani 1 1 d . . .
C2 C 0.7399(5) 0.1219(4) 0.7565(3) 0.0392(15) Uani 1 1 d . . .
C3 C 0.6542(5) 0.1143(5) 0.7890(3) 0.0472(18) Uani 1 1 d . . .
H3 H 0.5957 0.1108 0.7667 0.057 Uiso 1 1 calc R . .
C4 C 0.6498(5) 0.1114(5) 0.8546(3) 0.0424(17) Uani 1 1 d . . .
C5 C 0.7383(6) 0.1262(5) 0.9567(3) 0.0495(18) Uani 1 1 d . . .
H5 H 0.6789 0.1177 0.9773 0.059 Uiso 1 1 calc R . .
C6 C 0.8219(7) 0.1409(5) 0.9900(3) 0.060(2) Uani 1 1 d . . .
H6 H 0.8191 0.1427 1.0333 0.072 Uiso 1 1 calc R . .
C7 C 0.9110(6) 0.1530(6) 0.9603(4) 0.065(2) Uani 1 1 d . . .
H7 H 0.9674 0.1650 0.9835 0.078 Uiso 1 1 calc R . .
C8 C 0.9163(5) 0.1475(5) 0.8958(3) 0.0560(19) Uani 1 1 d . . .
H8 H 0.9763 0.1533 0.8755 0.067 Uiso 1 1 calc R . .
C9 C 0.8304(5) 0.1330(4) 0.8617(3) 0.0402(15) Uani 1 1 d . . .
C10 C 0.7415(5) 0.1239(4) 0.8924(3) 0.0401(15) Uani 1 1 d . . .
C11 C 0.8749(4) -0.0910(5) 0.6255(3) 0.0385(15) Uani 1 1 d . . .
C12 C 0.8699(5) -0.0269(5) 0.5682(3) 0.0388(15) Uani 1 1 d . . .
C13 C 0.8730(5) -0.0697(5) 0.5103(3) 0.0487(18) Uani 1 1 d . . .
H13 H 0.8712 -0.0297 0.4751 0.058 Uiso 1 1 calc R . .
C14 C 0.8789(5) -0.1727(6) 0.5022(3) 0.0489(17) Uani 1 1 d . . .
C15 C 0.8808(5) -0.3404(5) 0.5516(3) 0.0538(19) Uani 1 1 d . . .
H15 H 0.8831 -0.3681 0.5120 0.065 Uiso 1 1 calc R . .
C16 C 0.8810(5) -0.4004(5) 0.6035(4) 0.058(2) Uani 1 1 d . . .
H16 H 0.8827 -0.4682 0.5986 0.070 Uiso 1 1 calc R . .
C17 C 0.8789(5) -0.3611(5) 0.6613(4) 0.0550(19) Uani 1 1 d . . .
H17 H 0.8798 -0.4023 0.6959 0.066 Uiso 1 1 calc R . .
C18 C 0.8753(5) -0.2601(5) 0.6700(3) 0.0448(16) Uani 1 1 d . . .
H18 H 0.8727 -0.2341 0.7100 0.054 Uiso 1 1 calc R . .
C19 C 0.8756(4) -0.1983(5) 0.6187(3) 0.0400(15) Uani 1 1 d . . .
C20 C 0.8771(5) -0.2380(5) 0.5580(3) 0.0428(16) Uani 1 1 d . . .
H7A H 1.070(5) 0.137(5) 0.619(2) 0.064 Uiso 1 1 d D . .
H7B H 1.072(5) 0.048(3) 0.651(3) 0.064 Uiso 1 1 d D . .
H8A H 0.947(4) 0.306(4) 0.642(3) 0.064 Uiso 1 1 d D . .
H8B H 0.857(4) 0.313(4) 0.662(3) 0.064 Uiso 1 1 d D . .
O1S O 1.0663(7) 0.3555(6) 0.6335(4) 0.130(3) Uani 1 1 d D . .
C1S C 1.1325(14) 0.3453(11) 0.6924(9) 0.208(7) Uani 1 1 d DU . .
H1S1 H 1.1190 0.3983 0.7207 0.312 Uiso 1 1 calc R . .
H1S2 H 1.2002 0.3475 0.6802 0.312 Uiso 1 1 calc R . .
H1S3 H 1.1190 0.2839 0.7126 0.312 Uiso 1 1 calc R . .
H1S H 1.093(9) 0.313(10) 0.601(3) 0.312 Uiso 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
Co1 0.0417(5) 0.0300(5) 0.0305(4) -0.0006(4) 0.0068(4) 0.0082(4)
O1 0.047(3) 0.064(3) 0.044(3) -0.006(2) 0.009(2) 0.003(3)
O2 0.057(3) 0.059(3) 0.036(3) 0.003(2) 0.004(2) 0.016(3)
O3 0.049(3) 0.077(4) 0.064(3) -0.014(3) 0.016(3) -0.024(3)
O4 0.060(3) 0.044(3) 0.044(3) 0.001(2) 0.004(2) 0.002(2)
O5 0.079(4) 0.042(3) 0.048(3) 0.002(2) 0.007(2) 0.011(3)
O6 0.099(4) 0.059(3) 0.045(3) -0.006(2) 0.008(3) -0.008(3)
O7 0.057(3) 0.050(3) 0.062(3) 0.002(3) 0.015(2) 0.011(3)
O8 0.068(4) 0.046(3) 0.080(4) 0.001(3) 0.022(3) 0.013(3)
C1 0.041(4) 0.039(4) 0.041(4) 0.003(3) 0.005(3) 0.008(3)
C2 0.045(4) 0.033(4) 0.039(4) -0.003(3) -0.002(3) 0.007(3)
C3 0.044(4) 0.051(4) 0.047(4) -0.002(3) -0.002(3) -0.004(4)
C4 0.039(4) 0.038(4) 0.050(4) -0.004(3) 0.010(3) -0.010(3)
C5 0.062(5) 0.046(4) 0.040(4) 0.001(3) 0.001(3) -0.006(4)
C6 0.077(6) 0.061(5) 0.042(4) -0.002(4) -0.002(4) 0.004(5)
C7 0.068(6) 0.077(6) 0.050(5) -0.001(4) -0.012(4) 0.005(5)
C8 0.044(4) 0.064(5) 0.060(5) -0.010(4) -0.004(4) 0.002(4)
C9 0.042(4) 0.036(4) 0.042(3) 0.000(3) 0.008(3) 0.002(3)
C10 0.041(4) 0.036(4) 0.043(4) 0.002(3) 0.003(3) -0.004(3)
C11 0.035(4) 0.045(4) 0.036(4) -0.001(3) 0.008(3) -0.003(3)
C12 0.040(4) 0.037(4) 0.039(4) 0.000(3) 0.000(3) 0.002(3)
C13 0.059(5) 0.041(4) 0.046(4) 0.006(3) 0.007(3) -0.004(4)
C14 0.052(4) 0.055(5) 0.040(4) -0.001(3) 0.009(3) -0.005(4)
C15 0.055(5) 0.048(4) 0.058(5) -0.011(4) 0.001(4) -0.009(4)
C16 0.066(5) 0.035(4) 0.074(6) -0.003(4) 0.005(4) -0.007(4)
C17 0.067(5) 0.034(4) 0.065(5) 0.011(4) 0.010(4) 0.000(4)
C18 0.040(4) 0.048(4) 0.046(4) 0.003(3) 0.001(3) 0.000(3)
C19 0.038(4) 0.040(4) 0.042(4) 0.002(3) 0.005(3) -0.004(3)
C20 0.035(4) 0.042(4) 0.052(4) -0.004(3) 0.006(3) -0.003(3)
O1S 0.150(8) 0.098(6) 0.141(7) -0.009(5) 0.020(6) -0.013(5)
C1S 0.256(17) 0.134(12) 0.233(16) 0.014(12) -0.039(15) -0.022(12)
_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
Co1 O5 1.997(5) . ?
Co1 O8 2.046(5) . ?
Co1 O2 2.053(5) . ?
Co1 O7 2.080(5) . ?
Co1 O1 2.184(4) . ?
Co1 O4 2.302(4) . ?
O1 C1 1.237(7) . ?
O2 C2 1.278(7) . ?
O3 C4 1.243(7) . ?
O4 C11 1.232(7) . ?
O5 C12 1.279(7) . ?
O6 C14 1.252(7) . ?
C1 C9 1.479(9) . ?
C1 C2 1.510(9) . ?
C2 C3 1.363(9) . ?
C3 C4 1.409(9) . ?
C4 C10 1.499(9) . ?
C5 C6 1.359(10) . ?
C5 C10 1.381(8) . ?
C6 C7 1.381(11) . ?
C7 C8 1.387(10) . ?
C8 C9 1.393(9) . ?
C9 C10 1.384(8) . ?
C11 C19 1.470(9) . ?
C11 C12 1.509(8) . ?
C12 C13 1.372(9) . ?
C13 C14 1.417(10) . ?
C14 C20 1.490(9) . ?
C15 C16 1.382(9) . ?
C15 C20 1.402(9) . ?
C16 C17 1.350(9) . ?
C17 C18 1.390(9) . ?
C18 C19 1.384(8) . ?
C19 C20 1.410(8) . ?
O1S C1S 1.559(16) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 Co1 O8 100.5(2) . . ?
O5 Co1 O2 100.39(19) . . ?
O8 Co1 O2 92.2(2) . . ?
O5 Co1 O7 94.4(2) . . ?
O8 Co1 O7 90.4(2) . . ?
O2 Co1 O7 164.24(18) . . ?
O5 Co1 O1 162.26(19) . . ?
O8 Co1 O1 97.1(2) . . ?
O2 Co1 O1 77.04(17) . . ?
O7 Co1 O1 87.21(18) . . ?
O5 Co1 O4 76.31(17) . . ?
O8 Co1 O4 176.8(2) . . ?
O2 Co1 O4 87.85(17) . . ?
O7 Co1 O4 90.44(18) . . ?
O1 Co1 O4 86.02(16) . . ?
C1 O1 Co1 112.3(4) . . ?
C2 O2 Co1 116.8(4) . . ?
C11 O4 Co1 109.4(4) . . ?
C12 O5 Co1 118.1(4) . . ?
O1 C1 C9 122.8(6) . . ?
O1 C1 C2 118.3(6) . . ?
C9 C1 C2 118.9(6) . . ?
O2 C2 C3 126.7(6) . . ?
O2 C2 C1 115.0(6) . . ?
C3 C2 C1 118.3(6) . . ?
C2 C3 C4 123.2(6) . . ?
O3 C4 C3 121.8(6) . . ?
O3 C4 C10 118.2(6) . . ?
C3 C4 C10 120.0(6) . . ?
C6 C5 C10 120.1(7) . . ?
C5 C6 C7 120.9(7) . . ?
C6 C7 C8 119.9(7) . . ?
C7 C8 C9 119.2(7) . . ?
C10 C9 C8 119.9(6) . . ?
C10 C9 C1 120.2(6) . . ?
C8 C9 C1 119.9(6) . . ?
C5 C10 C9 120.0(6) . . ?
C5 C10 C4 121.0(6) . . ?
C9 C10 C4 119.0(6) . . ?
O4 C11 C19 122.2(6) . . ?
O4 C11 C12 117.9(6) . . ?
C19 C11 C12 119.8(5) . . ?
O5 C12 C13 124.0(6) . . ?
O5 C12 C11 116.8(5) . . ?
C13 C12 C11 119.2(6) . . ?
C12 C13 C14 122.2(6) . . ?
O6 C14 C13 122.0(6) . . ?
O6 C14 C20 118.5(7) . . ?
C13 C14 C20 119.5(6) . . ?
C16 C15 C20 120.7(7) . . ?
C17 C16 C15 120.3(7) . . ?
C16 C17 C18 121.1(7) . . ?
C19 C18 C17 119.7(6) . . ?
C18 C19 C20 120.0(6) . . ?
C18 C19 C11 121.8(6) . . ?
C20 C19 C11 118.2(5) . . ?
C15 C20 C19 118.2(6) . . ?
C15 C20 C14 121.0(6) . . ?
C19 C20 C14 120.8(6) . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H7A O6 0.92(2) 1.89(2) 2.803(7) 171(6) 5_756
O7 H7B O3 0.93(2) 1.81(3) 2.683(7) 156(6) 7_667
O8 H8A O1S 0.92(2) 1.77(3) 2.663(10) 165(7) .
O8 H8B O2 0.91(2) 1.84(3) 2.707(7) 159(7) 2_655
O1S H1S O6 0.97(2) 1.78(5) 2.730(9) 164(16) 5_756
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.36
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.801
_refine_diff_density_min         -0.723
_refine_diff_density_rms         0.096


data_compound3
_database_code_depnum_ccdc_archive 'CCDC 923819'
#TrackingRef 'Compound 3.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H22 Cu N4 O6'
_chemical_formula_weight         574.04
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'
Cu Cu 0.3201 1.2651 '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                   8.23410(10)
_cell_length_b                   8.2839(2)
_cell_length_c                   11.32100(10)
_cell_angle_alpha                69.6560(10)
_cell_angle_beta                 72.1980(10)
_cell_angle_gamma                61.0840(10)
_cell_volume                     624.801(18)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_description       Block
_exptl_crystal_colour            Brown
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             295
_exptl_absorpt_coefficient_mu    0.927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8364
_exptl_absorpt_correction_T_max  0.9130
_exptl_absorpt_process_details   
;
Sheldrick, G.M. SADABS: Program for absorption correction
using area detector data. University of G ttingen, Germany, 1996.
;
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Smart-CCD-1000 BRUKER'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4677
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0694
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         28.26
_reflns_number_total             2990
_reflns_number_gt                2268
_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    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0571P)^2^+0.5253P] where P=(Fo^2^+2Fc^2^)/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_number_reflns         2990
_refine_ls_number_parameters     179
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0636
_refine_ls_wR_factor_ref         0.1507
_refine_ls_wR_factor_gt          0.1322
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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
Cu1 Cu 1.0000 0.5000 0.5000 0.0355(2) Uani 1 2 d S . .
O1 O 0.9088(4) 0.2781(4) 0.6859(2) 0.0483(7) Uani 1 1 d . . .
O2 O 0.9012(4) 0.6244(4) 0.6422(2) 0.0427(6) Uani 1 1 d . . .
O3 O 0.7075(6) 0.5848(5) 1.0807(3) 0.0850(12) Uani 1 1 d . . .
N1 N 1.2593(4) 0.3776(4) 0.5445(3) 0.0413(7) Uani 1 1 d . . .
N2 N 1.5651(5) 0.2161(5) 0.5352(4) 0.0532(9) Uani 1 1 d . . .
C1 C 0.8586(5) 0.3473(5) 0.7764(3) 0.0367(8) Uani 1 1 d . . .
C2 C 0.8573(5) 0.5381(5) 0.7578(3) 0.0377(8) Uani 1 1 d . . .
C3 C 0.8098(6) 0.6092(6) 0.8607(4) 0.0516(10) Uani 1 1 d . . .
H3 H 0.8145 0.7240 0.8481 0.062 Uiso 1 1 calc R . .
C4 C 0.7520(6) 0.5158(6) 0.9893(4) 0.0517(10) Uani 1 1 d . . .
C5 C 0.6879(7) 0.2396(7) 1.1316(4) 0.0597(12) Uani 1 1 d . . .
H5 H 0.6540 0.2926 1.2004 0.072 Uiso 1 1 calc R . .
C6 C 0.6814(7) 0.0701(7) 1.1496(5) 0.0696(14) Uani 1 1 d . . .
H6 H 0.6437 0.0087 1.2315 0.084 Uiso 1 1 calc R . .
C7 C 0.7290(7) -0.0111(7) 1.0499(5) 0.0634(12) Uani 1 1 d . . .
H7 H 0.7217 -0.1250 1.0639 0.076 Uiso 1 1 calc R . .
C8 C 0.7882(6) 0.0792(6) 0.9280(4) 0.0527(10) Uani 1 1 d . . .
H8 H 0.8221 0.0249 0.8598 0.063 Uiso 1 1 calc R . .
C9 C 0.7968(5) 0.2499(5) 0.9076(4) 0.0414(8) Uani 1 1 d . . .
C10 C 0.7457(6) 0.3316(6) 1.0092(4) 0.0453(9) Uani 1 1 d . . .
C11 C 1.4181(5) 0.2662(6) 0.4824(4) 0.0475(9) Uani 1 1 d . . .
H11 H 1.4253 0.2285 0.4118 0.057 Uiso 1 1 calc R . .
C12 C 1.5003(6) 0.2959(7) 0.6356(4) 0.0570(11) Uani 1 1 d . . .
H12 H 1.5713 0.2844 0.6905 0.068 Uiso 1 1 calc R . .
C13 C 1.3144(6) 0.3943(6) 0.6406(4) 0.0508(10) Uani 1 1 d . . .
H13 H 1.2339 0.4642 0.7008 0.061 Uiso 1 1 calc R . .
C14 C 1.7621(6) 0.0988(8) 0.4906(6) 0.0814(17) Uani 1 1 d . . .
H14A H 1.8099 -0.0132 0.5568 0.122 Uiso 1 1 calc R . .
H14B H 1.8351 0.1699 0.4696 0.122 Uiso 1 1 calc R . .
H14C H 1.7705 0.0630 0.4161 0.122 Uiso 1 1 calc R . .
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
Cu1 0.0379(4) 0.0378(4) 0.0309(3) -0.0078(3) -0.0059(3) -0.0163(3)
O1 0.0666(18) 0.0496(16) 0.0370(14) -0.0156(12) -0.0045(13) -0.0298(14)
O2 0.0551(16) 0.0390(14) 0.0352(13) -0.0056(11) -0.0073(12) -0.0230(12)
O3 0.147(4) 0.084(3) 0.0442(17) -0.0306(17) 0.005(2) -0.066(3)
N1 0.0406(18) 0.0466(18) 0.0373(16) -0.0056(14) -0.0070(14) -0.0217(15)
N2 0.0384(19) 0.047(2) 0.065(2) 0.0039(18) -0.0168(17) -0.0177(16)
C1 0.0368(19) 0.0383(19) 0.0348(18) -0.0095(15) -0.0088(15) -0.0138(16)
C2 0.0377(19) 0.039(2) 0.0380(18) -0.0101(16) -0.0065(15) -0.0165(16)
C3 0.072(3) 0.048(2) 0.046(2) -0.0166(19) -0.006(2) -0.033(2)
C4 0.071(3) 0.054(2) 0.037(2) -0.0185(19) -0.0007(19) -0.032(2)
C5 0.071(3) 0.062(3) 0.040(2) -0.011(2) 0.002(2) -0.031(2)
C6 0.079(3) 0.061(3) 0.055(3) -0.003(2) 0.006(2) -0.036(3)
C7 0.079(3) 0.047(3) 0.063(3) -0.001(2) -0.007(2) -0.036(2)
C8 0.067(3) 0.046(2) 0.050(2) -0.0079(19) -0.009(2) -0.031(2)
C9 0.041(2) 0.040(2) 0.041(2) -0.0073(17) -0.0113(16) -0.0153(17)
C10 0.043(2) 0.047(2) 0.040(2) -0.0105(17) -0.0027(17) -0.0175(18)
C11 0.039(2) 0.051(2) 0.047(2) -0.0069(19) -0.0084(18) -0.0181(19)
C12 0.055(3) 0.066(3) 0.058(3) 0.001(2) -0.023(2) -0.034(2)
C13 0.054(3) 0.059(3) 0.044(2) -0.0062(19) -0.0130(19) -0.029(2)
C14 0.039(3) 0.070(3) 0.111(5) -0.011(3) -0.011(3) -0.012(2)
_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
Cu1 O2 1.964(2) 2_766 ?
Cu1 O2 1.964(2) . ?
Cu1 N1 2.012(3) . ?
Cu1 N1 2.012(3) 2_766 ?
O1 C1 1.213(4) . ?
O2 C2 1.291(4) . ?
O3 C4 1.228(5) . ?
N1 C11 1.333(5) . ?
N1 C13 1.370(5) . ?
N2 C11 1.334(5) . ?
N2 C12 1.350(6) . ?
N2 C14 1.465(6) . ?
C1 C9 1.490(5) . ?
C1 C2 1.515(5) . ?
C2 C3 1.354(5) . ?
C3 C4 1.447(6) . ?
C4 C10 1.487(6) . ?
C5 C6 1.372(7) . ?
C5 C10 1.392(6) . ?
C6 C7 1.371(7) . ?
C7 C8 1.387(6) . ?
C8 C9 1.385(5) . ?
C9 C10 1.389(5) . ?
C12 C13 1.335(6) . ?
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 Cu1 O2 180 2_766 . ?
O2 Cu1 N1 90.44(12) 2_766 . ?
O2 Cu1 N1 89.56(12) . . ?
O2 Cu1 N1 89.56(12) 2_766 2_766 ?
O2 Cu1 N1 90.44(12) . 2_766 ?
N1 Cu1 N1 180 . 2_766 ?
C2 O2 Cu1 121.7(2) . . ?
C11 N1 C13 104.6(3) . . ?
C11 N1 Cu1 126.8(3) . . ?
C13 N1 Cu1 128.5(3) . . ?
C11 N2 C12 107.8(4) . . ?
C11 N2 C14 126.1(4) . . ?
C12 N2 C14 126.1(4) . . ?
O1 C1 C9 121.8(3) . . ?
O1 C1 C2 120.1(3) . . ?
C9 C1 C2 118.1(3) . . ?
O2 C2 C3 123.8(3) . . ?
O2 C2 C1 116.8(3) . . ?
C3 C2 C1 119.4(3) . . ?
C2 C3 C4 123.4(4) . . ?
O3 C4 C3 122.0(4) . . ?
O3 C4 C10 119.9(4) . . ?
C3 C4 C10 118.2(3) . . ?
C6 C5 C10 119.4(4) . . ?
C7 C6 C5 121.8(4) . . ?
C6 C7 C8 119.1(4) . . ?
C9 C8 C7 120.2(4) . . ?
C8 C9 C10 120.1(4) . . ?
C8 C9 C1 120.0(4) . . ?
C10 C9 C1 119.9(3) . . ?
C9 C10 C5 119.5(4) . . ?
C9 C10 C4 121.0(3) . . ?
C5 C10 C4 119.6(4) . . ?
N1 C11 N2 110.8(4) . . ?
C13 C12 N2 106.6(4) . . ?
C12 C13 N1 110.2(4) . . ?
_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        28.26
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.661
_refine_diff_density_min         -0.656
_refine_diff_density_rms         0.081


data_zn
_database_code_depnum_ccdc_archive 'CCDC 923820'
#TrackingRef 'zn.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H18 N2 O6 Zn'
_chemical_formula_weight         567.83
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           Orthorhombic
_symmetry_space_group_name_H-M   'A b a 2'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z+1/2'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z+1'
'x+1/2, -y+1/2, z+1'
_cell_length_a                   19.6716(11)
_cell_length_b                   14.8036(8)
_cell_length_c                   8.3806(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2440.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_exptl_crystal_description       Plate
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1160
_exptl_absorpt_coefficient_mu    1.057
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7421
_exptl_absorpt_correction_T_max  0.9490
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Smart-CCD-1000 BRUKER'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8661
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_sigmaI/netI    0.0557
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         28.27
_reflns_number_total             2782
_reflns_number_gt                1959
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'BRUKER Smart'
_computing_cell_refinement       'BRUKER Smart'
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0286P)^2^+1.1880P] where P=(Fo^2^+2Fc^2^)/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   0.04(2)
_refine_ls_number_reflns         2782
_refine_ls_number_parameters     177
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.0875
_refine_ls_wR_factor_gt          0.0758
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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 0.0000 1.0000 0.92096(12) 0.03840(14) Uani 1 2 d S . .
O1 O 0.09186(10) 0.91352(13) 0.9128(5) 0.0452(5) Uani 1 1 d . . .
O2 O 0.06222(13) 1.06895(17) 0.7738(3) 0.0532(7) Uani 1 1 d . . .
O3 O 0.29208(18) 1.0915(2) 0.6204(5) 0.0832(12) Uani 1 1 d . . .
N1 N 0.02757(15) 1.0809(2) 1.1211(4) 0.0463(8) Uani 1 1 d . . .
C1 C 0.13923(17) 0.9531(2) 0.8469(4) 0.0365(7) Uani 1 1 d . . .
C2 C 0.12475(18) 1.0419(2) 0.7655(5) 0.0423(8) Uani 1 1 d . . .
C3 C 0.1769(2) 1.0844(3) 0.6897(6) 0.0549(11) Uani 1 1 d . . .
H3 H 0.1676 1.1378 0.6355 0.066 Uiso 1 1 calc R . .
C4 C 0.2454(2) 1.0516(2) 0.6886(7) 0.0545(11) Uani 1 1 d . . .
C5 C 0.32599(19) 0.9290(3) 0.7748(6) 0.0620(12) Uani 1 1 d . . .
H5 H 0.3612 0.9615 0.7277 0.074 Uiso 1 1 calc R . .
C6 C 0.3397(2) 0.8468(3) 0.8459(6) 0.0663(13) Uani 1 1 d . . .
H6 H 0.3838 0.8241 0.8459 0.080 Uiso 1 1 calc R . .
C7 C 0.28790(18) 0.7983(3) 0.9167(9) 0.0644(10) Uani 1 1 d . . .
H7 H 0.2969 0.7430 0.9649 0.077 Uiso 1 1 calc R . .
C8 C 0.22243(15) 0.8326(2) 0.9156(8) 0.0501(8) Uani 1 1 d . . .
H8 H 0.1875 0.8000 0.9632 0.060 Uiso 1 1 calc R . .
C9 C 0.20841(17) 0.9153(2) 0.8438(5) 0.0402(8) Uani 1 1 d . . .
C10 C 0.26095(19) 0.9638(3) 0.7728(5) 0.0464(9) Uani 1 1 d . . .
C11 C 0.01401(17) 1.0464(3) 1.2654(5) 0.0543(10) Uani 1 1 d . . .
C12 C 0.0261(2) 1.0962(5) 1.4028(8) 0.0930(19) Uani 1 1 d . . .
H12 H 0.0172 1.0718 1.5029 0.112 Uiso 1 1 calc R . .
C13 C 0.0520(3) 1.1835(6) 1.3878(10) 0.125(3) Uani 1 1 d . . .
H13 H 0.0598 1.2188 1.4778 0.150 Uiso 1 1 calc R . .
C14 C 0.0653(3) 1.2153(4) 1.2437(11) 0.112(3) Uani 1 1 d . . .
H14 H 0.0832 1.2731 1.2329 0.135 Uiso 1 1 calc R . .
C15 C 0.0530(2) 1.1638(3) 1.1082(7) 0.0702(13) Uani 1 1 d . . .
H15 H 0.0627 1.1875 1.0079 0.084 Uiso 1 1 calc R . .
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
Zn1 0.0401(2) 0.0419(2) 0.0331(2) 0.000 0.000 0.0029(3)
O1 0.0391(11) 0.0389(10) 0.0577(15) 0.0067(18) 0.0061(18) -0.0023(9)
O2 0.0546(17) 0.0568(16) 0.0481(17) 0.0178(14) 0.0036(14) 0.0110(13)
O3 0.062(2) 0.078(2) 0.110(3) 0.037(2) 0.018(2) -0.0184(17)
N1 0.0418(16) 0.0523(19) 0.045(2) -0.0097(16) -0.0083(16) 0.0059(15)
C1 0.0437(19) 0.0323(17) 0.0336(17) -0.0028(15) 0.0034(16) -0.0039(15)
C2 0.049(2) 0.0426(18) 0.035(2) 0.0068(18) 0.0034(19) 0.0030(17)
C3 0.062(3) 0.045(2) 0.057(3) 0.016(2) 0.010(2) -0.005(2)
C4 0.050(2) 0.056(2) 0.057(3) 0.013(3) 0.001(2) -0.014(2)
C5 0.038(2) 0.083(3) 0.065(3) 0.003(3) 0.007(2) -0.014(2)
C6 0.037(2) 0.073(3) 0.089(4) 0.011(3) 0.001(2) 0.004(2)
C7 0.057(2) 0.057(2) 0.080(3) 0.007(3) -0.003(4) 0.0074(17)
C8 0.0400(17) 0.0432(17) 0.067(2) 0.000(3) 0.003(3) -0.0031(13)
C9 0.0354(18) 0.0418(18) 0.043(2) 0.0000(17) 0.0014(17) -0.0064(15)
C10 0.042(2) 0.0484(19) 0.049(2) 0.0026(18) -0.0008(19) -0.0097(17)
C11 0.039(2) 0.086(3) 0.038(2) -0.014(2) -0.0098(17) 0.0243(19)
C12 0.065(3) 0.166(5) 0.048(3) -0.036(4) -0.017(3) 0.045(3)
C13 0.074(4) 0.180(7) 0.121(7) -0.111(6) -0.042(5) 0.042(4)
C14 0.077(4) 0.089(4) 0.170(8) -0.085(5) -0.042(5) 0.009(3)
C15 0.059(3) 0.056(3) 0.096(4) -0.015(3) -0.016(3) 0.002(2)
_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
Zn1 O2 2.015(3) 2_575 ?
Zn1 O2 2.015(3) . ?
Zn1 N1 2.131(3) . ?
Zn1 N1 2.131(3) 2_575 ?
Zn1 O1 2.216(2) . ?
Zn1 O1 2.216(2) 2_575 ?
O1 C1 1.232(4) . ?
O2 C2 1.295(4) . ?
O3 C4 1.233(5) . ?
N1 C15 1.331(5) . ?
N1 C11 1.340(5) . ?
C1 C9 1.471(5) . ?
C1 C2 1.508(5) . ?
C2 C3 1.362(5) . ?
C3 C4 1.431(6) . ?
C4 C10 1.510(6) . ?
C5 C10 1.379(5) . ?
C5 C6 1.382(6) . ?
C6 C7 1.380(6) . ?
C7 C8 1.384(4) . ?
C8 C9 1.392(5) . ?
C9 C10 1.392(5) . ?
C11 C12 1.388(7) . ?
C11 C11 1.480(9) 2_575 ?
C12 C13 1.395(10) . ?
C13 C14 1.323(11) . ?
C14 C15 1.389(8) . ?
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 Zn1 O2 104.54(17) 2_575 . ?
O2 Zn1 N1 157.05(10) 2_575 . ?
O2 Zn1 N1 92.43(13) . . ?
O2 Zn1 N1 92.43(13) 2_575 2_575 ?
O2 Zn1 N1 157.05(10) . 2_575 ?
N1 Zn1 N1 76.17(19) . 2_575 ?
O2 Zn1 O1 100.60(11) 2_575 . ?
O2 Zn1 O1 77.20(10) . . ?
N1 Zn1 O1 98.12(13) . . ?
N1 Zn1 O1 84.67(12) 2_575 . ?
O2 Zn1 O1 77.20(10) 2_575 2_575 ?
O2 Zn1 O1 100.60(11) . 2_575 ?
N1 Zn1 O1 84.67(12) . 2_575 ?
N1 Zn1 O1 98.12(13) 2_575 2_575 ?
O1 Zn1 O1 176.5(2) . 2_575 ?
C1 O1 Zn1 110.9(2) . . ?
C2 O2 Zn1 116.9(2) . . ?
C15 N1 C11 120.0(4) . . ?
C15 N1 Zn1 123.4(3) . . ?
C11 N1 Zn1 116.5(3) . . ?
O1 C1 C9 121.8(3) . . ?
O1 C1 C2 118.3(3) . . ?
C9 C1 C2 119.9(3) . . ?
O2 C2 C3 126.7(4) . . ?
O2 C2 C1 115.1(3) . . ?
C3 C2 C1 118.1(3) . . ?
C2 C3 C4 123.7(4) . . ?
O3 C4 C3 122.8(4) . . ?
O3 C4 C10 118.5(4) . . ?
C3 C4 C10 118.7(3) . . ?
C10 C5 C6 121.0(4) . . ?
C7 C6 C5 119.9(4) . . ?
C6 C7 C8 119.6(4) . . ?
C7 C8 C9 120.6(4) . . ?
C8 C9 C10 119.4(3) . . ?
C8 C9 C1 120.7(3) . . ?
C10 C9 C1 119.9(3) . . ?
C5 C10 C9 119.4(4) . . ?
C5 C10 C4 121.0(4) . . ?
C9 C10 C4 119.5(3) . . ?
N1 C11 C12 120.8(5) . . ?
N1 C11 C11 115.3(2) . 2_575 ?
C12 C11 C11 123.9(4) . 2_575 ?
C11 C12 C13 118.7(7) . . ?
C14 C13 C12 118.9(6) . . ?
C13 C14 C15 121.2(7) . . ?
N1 C15 C14 120.4(6) . . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.27
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.054