# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_lk
_database_code_depnum_ccdc_archive 'CCDC 1021427'
#Added by publCIF



_audit_update_record             
;
2014-08-27 deposited with the CCDC.
2016-02-05 downloaded from the CCDC.
;


_symmetry_space_group_name_hall  '-C 2yc'
#Added by publCIF




_cell_special_details            ?

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H4 Cu2 N4 O4'
_chemical_formula_weight         347.23

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           monoclinic
_symmetry_space_group_name_H-M   'C 2/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                   15.4753(9)
_cell_length_b                   4.9036(2)
_cell_length_c                   12.9752(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.423(5)
_cell_angle_gamma                90.00
_cell_volume                     961.56(8)
_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       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    4.436
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.48236
_exptl_absorpt_correction_T_max  1.00000
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2019
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         28.85
_reflns_number_total             1104
_reflns_number_gt                934
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0558P)²+2.5270P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1104
_refine_ls_number_parameters     82
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1097
_refine_ls_wR_factor_gt          0.0994
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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 0.25926(3) 0.17010(10) 0.14846(3) 0.0262(2) Uani 1 1 d . . .
C1 C 0.3508(3) 0.2077(9) 0.3569(3) 0.0306(9) Uani 1 1 d . . .
C2 C 0.1357(3) -0.1883(8) 0.0345(3) 0.0272(9) Uani 1 1 d . . .
C3 C 0.0831(3) -0.2725(11) -0.0611(4) 0.0366(10) Uani 1 1 d . . .
H3 H 0.0407 -0.4097 -0.0732 0.044 Uiso 1 1 calc R . .
C4 C 0.1093(3) -0.1031(10) -0.1336(3) 0.0332(10) Uani 1 1 d . . .
H4 H 0.0860 -0.1080 -0.2059 0.040 Uiso 1 1 calc R . .
N1 N 0.1734(2) 0.0717(7) -0.0857(3) 0.0269(7) Uani 1 1 d . . .
N2 N 0.1888(2) 0.0156(7) 0.0190(2) 0.0243(7) Uani 1 1 d . . .
O1 O 0.3850(2) 0.0001(8) 0.3317(3) 0.0482(9) Uani 1 1 d . . .
O2 O 0.29370(19) 0.3536(6) 0.2883(2) 0.0274(6) Uani 1 1 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
Cu1 0.0326(3) 0.0294(3) 0.0142(3) -0.00021(18) -0.0005(2) -0.0037(2)
C1 0.028(2) 0.039(2) 0.023(2) -0.0045(18) 0.0032(17) -0.0007(19)
C2 0.026(2) 0.031(2) 0.022(2) 0.0023(16) -0.0016(16) 0.0000(17)
C3 0.031(2) 0.048(3) 0.027(2) -0.001(2) -0.0029(18) -0.009(2)
C4 0.031(2) 0.046(2) 0.019(2) -0.0012(19) -0.0030(16) -0.011(2)
N1 0.0296(17) 0.0333(18) 0.0151(15) 0.0025(14) -0.0011(13) -0.0007(15)
N2 0.0304(17) 0.0263(17) 0.0141(14) 0.0010(13) 0.0002(12) 0.0003(14)
O1 0.049(2) 0.057(2) 0.0332(18) -0.0149(17) -0.0032(15) 0.0234(18)
O2 0.0320(15) 0.0313(15) 0.0168(13) -0.0010(11) 0.0005(11) 0.0003(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
Cu1 N1 1.929(3) 7 ?
Cu1 N2 1.948(3) . ?
Cu1 O2 1.993(3) . ?
Cu1 O2 2.010(3) 4_545 ?
C1 O1 1.224(5) . ?
C1 O2 1.321(5) . ?
C1 C2 1.470(6) 4 ?
C2 N2 1.336(5) . ?
C2 C3 1.392(6) . ?
C2 C1 1.470(6) 4_545 ?
C3 C4 1.379(7) . ?
C3 H3 0.9300 . ?
C4 N1 1.356(5) . ?
C4 H4 0.9300 . ?
N1 N2 1.356(4) . ?
N1 Cu1 1.929(3) 7 ?
O2 Cu1 2.010(3) 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
N1 Cu1 N2 98.30(13) 7 . ?
N1 Cu1 O2 91.44(13) 7 . ?
N2 Cu1 O2 162.00(13) . . ?
N1 Cu1 O2 169.73(14) 7 4_545 ?
N2 Cu1 O2 81.36(12) . 4_545 ?
O2 Cu1 O2 91.70(7) . 4_545 ?
O1 C1 O2 122.3(4) . . ?
O1 C1 C2 124.3(4) . 4 ?
O2 C1 C2 113.2(4) . 4 ?
N2 C2 C3 110.4(4) . . ?
N2 C2 C1 116.0(4) . 4_545 ?
C3 C2 C1 133.3(4) . 4_545 ?
C4 C3 C2 103.1(4) . . ?
C4 C3 H3 128.4 . . ?
C2 C3 H3 128.4 . . ?
N1 C4 C3 111.2(4) . . ?
N1 C4 H4 124.4 . . ?
C3 C4 H4 124.4 . . ?
N2 N1 C4 106.6(3) . . ?
N2 N1 Cu1 124.2(3) . 7 ?
C4 N1 Cu1 129.0(3) . 7 ?
C2 N2 N1 108.7(3) . . ?
C2 N2 Cu1 114.2(3) . . ?
N1 N2 Cu1 136.9(3) . . ?
C1 O2 Cu1 112.2(3) . . ?
C1 O2 Cu1 114.5(3) . 4 ?
Cu1 O2 Cu1 131.87(15) . 4 ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        28.85
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.735
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.130

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a-82
_database_code_depnum_ccdc_archive 'CCDC 1021428'
#Added by publCIF



_audit_update_record             
;
2014-08-27 deposited with the CCDC.
2016-02-05 downloaded from the CCDC.
;


_symmetry_space_group_name_hall  '-P 2yn'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H20 N4 Ni2 O12'
_chemical_formula_weight         481.70

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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/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                   8.2122(4)
_cell_length_b                   9.1298(4)
_cell_length_c                   12.1575(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.134(5)
_cell_angle_gamma                90.00
_cell_volume                     871.06(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.837
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    2.230
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           ?

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4036
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.42
_diffrn_reflns_theta_max         26.36
_reflns_number_total             1780
_reflns_number_gt                1488
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0431P)²+0.8402P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1780
_refine_ls_number_parameters     124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1019
_refine_ls_wR_factor_gt          0.0948
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_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
Ni1 Ni 0.82653(5) 0.35814(5) 0.40832(4) 0.02124(17) Uani 1 1 d . . .
O1 O 0.8795(3) 0.1466(3) 0.3568(2) 0.0269(6) Uani 1 1 d . . .
O3 O 0.8458(5) 0.4195(4) 0.7471(3) 0.0528(8) Uani 1 1 d G . .
H3A H 0.8299 0.4846 0.6950 0.079 Uiso 1 1 d G . .
H3B H 0.7900 0.4417 0.7936 0.079 Uiso 1 1 d G . .
O2 O 1.0959(3) -0.0002(3) 0.3573(2) 0.0317(6) Uani 1 1 d . . .
O5 O 0.8483(3) 0.4343(3) 0.2452(2) 0.0292(6) Uani 1 1 d . . .
H5A H 0.9460 0.4747 0.2543 0.044 Uiso 1 1 d R . .
H5B H 0.7700 0.4979 0.2166 0.044 Uiso 1 1 d R . .
N2 N 1.0842(4) 0.3498(3) 0.4799(2) 0.0217(6) Uani 1 1 d . . .
N1 N 1.2119(3) 0.4367(3) 0.5414(2) 0.0226(6) Uani 1 1 d . . .
C1 C 1.1541(4) 0.2247(4) 0.4567(3) 0.0223(7) Uani 1 1 d . . .
C2 C 1.3290(4) 0.2288(4) 0.5033(3) 0.0266(8) Uani 1 1 d . . .
H2 H 1.4078 0.1570 0.5002 0.032 Uiso 1 1 calc R . .
C3 C 1.0356(5) 0.1153(4) 0.3859(3) 0.0236(8) Uani 1 1 d . . .
C4 C 1.3596(5) 0.3642(4) 0.5554(3) 0.0268(8) Uani 1 1 d . . .
H4 H 1.4668 0.4005 0.5946 0.032 Uiso 1 1 calc R . .
O4 O 0.5726(3) 0.3296(3) 0.3191(2) 0.0365(7) Uani 1 1 d . . .
H4A H 0.5500 0.2379 0.3079 0.055 Uiso 1 1 d R . .
H4B H 0.5507 0.3726 0.2535 0.055 Uiso 1 1 d R . .
O6 O 0.7660(3) 0.2606(3) 0.5456(2) 0.0319(6) Uani 1 1 d . . .
H6A H 0.6575 0.2480 0.5289 0.048 Uiso 1 1 d R . .
H6B H 0.7987 0.3158 0.6054 0.048 Uiso 1 1 d 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
Ni1 0.0212(3) 0.0171(3) 0.0227(3) -0.00147(18) 0.00228(19) 0.00028(17)
O1 0.0262(14) 0.0202(13) 0.0313(14) -0.0072(11) 0.0036(11) -0.0008(10)
O3 0.067(2) 0.049(2) 0.053(2) -0.0060(17) 0.0353(18) -0.0073(17)
O2 0.0357(15) 0.0185(13) 0.0363(15) -0.0077(12) 0.0036(11) 0.0061(11)
O5 0.0267(13) 0.0304(15) 0.0286(13) 0.0017(12) 0.0054(11) 0.0024(11)
N2 0.0215(15) 0.0162(15) 0.0246(15) -0.0025(12) 0.0024(12) 0.0013(11)
N1 0.0191(14) 0.0198(15) 0.0261(15) -0.0016(13) 0.0024(12) -0.0007(12)
C1 0.0279(19) 0.0182(17) 0.0206(17) -0.0006(15) 0.0069(14) 0.0040(14)
C2 0.0251(19) 0.0248(19) 0.0283(19) -0.0024(16) 0.0054(15) 0.0060(15)
C3 0.0274(19) 0.0216(18) 0.0196(17) 0.0011(15) 0.0033(14) 0.0016(14)
C4 0.0205(18) 0.027(2) 0.0302(19) -0.0017(16) 0.0030(15) 0.0012(14)
O4 0.0281(14) 0.0313(16) 0.0391(16) 0.0098(13) -0.0073(12) -0.0073(11)
O6 0.0323(15) 0.0321(15) 0.0309(14) 0.0023(12) 0.0089(12) 0.0001(11)

_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
Ni1 N1 2.024(3) 3_766 ?
Ni1 N2 2.038(3) . ?
Ni1 O4 2.064(2) . ?
Ni1 O6 2.077(3) . ?
Ni1 O1 2.115(2) . ?
Ni1 O5 2.158(3) . ?
O1 C3 1.258(4) . ?
O3 H3A 0.8500 . ?
O3 H3B 0.8502 . ?
O2 C3 1.257(4) . ?
O5 H5A 0.8600 . ?
O5 H5B 0.8597 . ?
N2 C1 1.345(4) . ?
N2 N1 1.351(4) . ?
N1 C4 1.348(4) . ?
N1 Ni1 2.024(3) 3_766 ?
C1 C2 1.381(5) . ?
C1 C3 1.480(5) . ?
C2 C4 1.378(5) . ?
C2 H2 0.9300 . ?
C4 H4 0.9300 . ?
O4 H4A 0.8591 . ?
O4 H4B 0.8589 . ?
O6 H6A 0.8607 . ?
O6 H6B 0.8605 . ?

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 Ni1 N2 98.05(11) 3_766 . ?
N1 Ni1 O4 93.02(11) 3_766 . ?
N2 Ni1 O4 168.68(12) . . ?
N1 Ni1 O6 93.36(11) 3_766 . ?
N2 Ni1 O6 96.04(11) . . ?
O4 Ni1 O6 85.64(11) . . ?
N1 Ni1 O1 177.13(10) 3_766 . ?
N2 Ni1 O1 79.29(10) . . ?
O4 Ni1 O1 89.60(10) . . ?
O6 Ni1 O1 88.01(10) . . ?
N1 Ni1 O5 92.39(11) 3_766 . ?
N2 Ni1 O5 92.75(11) . . ?
O4 Ni1 O5 84.38(10) . . ?
O6 Ni1 O5 168.72(10) . . ?
O1 Ni1 O5 86.68(10) . . ?
C3 O1 Ni1 113.9(2) . . ?
H3A O3 H3B 109.5 . . ?
Ni1 O5 H5A 110.2 . . ?
Ni1 O5 H5B 109.5 . . ?
H5A O5 H5B 108.7 . . ?
C1 N2 N1 107.7(3) . . ?
C1 N2 Ni1 113.3(2) . . ?
N1 N2 Ni1 138.9(2) . . ?
C4 N1 N2 107.8(3) . . ?
C4 N1 Ni1 129.1(2) . 3_766 ?
N2 N1 Ni1 123.1(2) . 3_766 ?
N2 C1 C2 110.4(3) . . ?
N2 C1 C3 116.5(3) . . ?
C2 C1 C3 133.1(3) . . ?
C4 C2 C1 103.9(3) . . ?
C4 C2 H2 128.1 . . ?
C1 C2 H2 128.1 . . ?
O2 C3 O1 124.4(3) . . ?
O2 C3 C1 118.8(3) . . ?
O1 C3 C1 116.8(3) . . ?
N1 C4 C2 110.3(3) . . ?
N1 C4 H4 124.9 . . ?
C2 C4 H4 124.9 . . ?
Ni1 O4 H4A 110.1 . . ?
Ni1 O4 H4B 109.4 . . ?
H4A O4 H4B 108.8 . . ?
Ni1 O6 H6A 110.1 . . ?
Ni1 O6 H6B 109.8 . . ?
H6A O6 H6B 108.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Ni1 O1 C3 19(2) 3_766 . . . ?
N2 Ni1 O1 C3 -3.3(2) . . . . ?
O4 Ni1 O1 C3 174.5(2) . . . . ?
O6 Ni1 O1 C3 -99.8(2) . . . . ?
O5 Ni1 O1 C3 90.1(2) . . . . ?
N1 Ni1 N2 C1 -176.9(2) 3_766 . . . ?
O4 Ni1 N2 C1 -9.2(7) . . . . ?
O6 Ni1 N2 C1 88.8(2) . . . . ?
O1 Ni1 N2 C1 2.0(2) . . . . ?
O5 Ni1 N2 C1 -84.1(2) . . . . ?
N1 Ni1 N2 N1 -0.9(4) 3_766 . . . ?
O4 Ni1 N2 N1 166.9(5) . . . . ?
O6 Ni1 N2 N1 -95.2(3) . . . . ?
O1 Ni1 N2 N1 178.0(4) . . . . ?
O5 Ni1 N2 N1 91.9(3) . . . . ?
C1 N2 N1 C4 0.1(4) . . . . ?
Ni1 N2 N1 C4 -176.1(3) . . . . ?
C1 N2 N1 Ni1 177.2(2) . . . 3_766 ?
Ni1 N2 N1 Ni1 1.0(5) . . . 3_766 ?
N1 N2 C1 C2 0.1(4) . . . . ?
Ni1 N2 C1 C2 177.4(2) . . . . ?
N1 N2 C1 C3 -178.0(3) . . . . ?
Ni1 N2 C1 C3 -0.7(4) . . . . ?
N2 C1 C2 C4 -0.3(4) . . . . ?
C3 C1 C2 C4 177.4(4) . . . . ?
Ni1 O1 C3 O2 -174.9(3) . . . . ?
Ni1 O1 C3 C1 3.9(4) . . . . ?
N2 C1 C3 O2 176.6(3) . . . . ?
C2 C1 C3 O2 -1.0(6) . . . . ?
N2 C1 C3 O1 -2.2(5) . . . . ?
C2 C1 C3 O1 -179.8(4) . . . . ?
N2 N1 C4 C2 -0.2(4) . . . . ?
Ni1 N1 C4 C2 -177.2(2) 3_766 . . . ?
C1 C2 C4 N1 0.3(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
O4 H4B O2 0.86 1.91 2.680(4) 148.0 2_655
O4 H4A O3 0.86 2.17 2.906(4) 144.0 4_565
O5 H5B O1 0.86 1.87 2.725(3) 171.8 2_655
O5 H5A O3 0.86 1.97 2.822(4) 171.5 3_766
O3 H3B O2 0.85 2.04 2.858(4) 161.8 4_566
O6 H6B O3 0.86 1.90 2.756(4) 170.5 .

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.36
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.652
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.092

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_co
_database_code_depnum_ccdc_archive 'CCDC 1021429'
#Added by publCIF



_audit_update_record             
;
2014-08-27 deposited with the CCDC.
2016-02-05 downloaded from the CCDC.
;


_symmetry_space_group_name_hall  '-P 2ybc'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H10 Co N4 O6'
_chemical_formula_weight         317.13

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   'P 21/c'

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

_cell_length_a                   5.1082(3)
_cell_length_b                   11.3902(7)
_cell_length_c                   9.3932(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.020(7)
_cell_angle_gamma                90.00
_cell_volume                     543.51(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.938
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             322
_exptl_absorpt_coefficient_mu    1.612
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           ?

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2211
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0455
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         3.58
_diffrn_reflns_theta_max         28.97
_reflns_number_total             1253
_reflns_number_gt                1008
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0297P)²+0.3399P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1253
_refine_ls_number_parameters     88
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0849
_refine_ls_wR_factor_gt          0.0767
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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 -0.0104(5) 0.7447(2) 0.5861(3) 0.0184(6) Uani 1 1 d . . .
Co1 Co 0.0000 0.5000 0.5000 0.01803(17) Uani 1 2 d S . .
N1 N 0.2710(4) 0.7541(2) 0.4349(2) 0.0231(5) Uani 1 1 d . . .
O1 O 0.2413(4) 0.42362(15) 0.3585(2) 0.0221(4) Uani 1 1 d . . .
C2 C 0.0733(6) 0.8612(2) 0.5832(3) 0.0259(6) Uani 1 1 d . . .
H2 H 0.0187 0.9239 0.6364 0.031 Uiso 1 1 calc R . .
N2 N 0.1134(4) 0.67935(18) 0.4951(2) 0.0192(5) Uani 1 1 d . . .
H1 H 0.3563 0.7346 0.3684 0.023 Uiso 1 1 d R . .
O2 O 0.3377(4) 0.25539(16) 0.2541(2) 0.0258(5) Uani 1 1 d . . .
C3 C 0.2541(6) 0.8632(2) 0.4847(3) 0.0272(7) Uani 1 1 d . . .
H3 H 0.3471 0.9283 0.4578 0.033 Uiso 1 1 calc R . .
O3 O 0.2876(4) 0.47418(16) 0.6719(2) 0.0246(4) Uani 1 1 d . . .
H3B H 0.3241 0.4009 0.7086 0.037 Uiso 1 1 d R . .
H3A H 0.4447 0.4977 0.6757 0.037 Uiso 1 1 d R . .
C4 C 0.2112(5) 0.3141(2) 0.3350(3) 0.0181(6) Uani 1 1 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
C1 0.0179(13) 0.0171(12) 0.0212(14) -0.0016(11) 0.0062(11) -0.0003(10)
Co1 0.0187(3) 0.0145(3) 0.0223(3) -0.0022(2) 0.0089(2) -0.0009(2)
N1 0.0240(12) 0.0258(12) 0.0219(12) 0.0001(10) 0.0133(10) -0.0028(10)
O1 0.0218(10) 0.0151(9) 0.0315(11) -0.0019(8) 0.0121(8) -0.0015(7)
C2 0.0322(16) 0.0168(13) 0.0304(16) -0.0034(12) 0.0105(12) -0.0002(12)
N2 0.0186(11) 0.0187(11) 0.0218(12) -0.0010(10) 0.0090(9) -0.0013(9)
O2 0.0270(11) 0.0231(10) 0.0300(11) -0.0076(9) 0.0162(9) -0.0016(8)
C3 0.0321(16) 0.0182(13) 0.0334(16) 0.0021(13) 0.0132(13) -0.0076(12)
O3 0.0192(10) 0.0245(10) 0.0302(11) 0.0070(9) 0.0032(8) -0.0037(8)
C4 0.0172(13) 0.0204(13) 0.0171(13) -0.0001(11) 0.0036(10) 0.0005(11)

_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
C1 N2 1.341(3) . ?
C1 C2 1.396(4) . ?
C1 C4 1.487(3) 3_566 ?
Co1 O3 2.0866(19) 3_566 ?
Co1 O3 2.0866(19) . ?
Co1 O1 2.0946(17) 3_566 ?
Co1 O1 2.0946(17) . ?
Co1 N2 2.125(2) . ?
Co1 N2 2.125(2) 3_566 ?
N1 C3 1.333(3) . ?
N1 N2 1.337(3) . ?
N1 H1 0.8288 . ?
O1 C4 1.273(3) . ?
C2 C3 1.375(4) . ?
C2 H2 0.9300 . ?
O2 C4 1.243(3) . ?
C3 H3 0.9300 . ?
O3 H3B 0.9147 . ?
O3 H3A 0.8434 . ?
C4 C1 1.487(3) 3_566 ?

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
N2 C1 C2 110.5(2) . . ?
N2 C1 C4 117.6(2) . 3_566 ?
C2 C1 C4 131.8(2) . 3_566 ?
O3 Co1 O3 180.0 3_566 . ?
O3 Co1 O1 91.10(7) 3_566 3_566 ?
O3 Co1 O1 88.90(7) . 3_566 ?
O3 Co1 O1 88.90(7) 3_566 . ?
O3 Co1 O1 91.10(7) . . ?
O1 Co1 O1 180.0 3_566 . ?
O3 Co1 N2 91.09(8) 3_566 . ?
O3 Co1 N2 88.91(8) . . ?
O1 Co1 N2 78.13(7) 3_566 . ?
O1 Co1 N2 101.87(7) . . ?
O3 Co1 N2 88.91(8) 3_566 3_566 ?
O3 Co1 N2 91.09(8) . 3_566 ?
O1 Co1 N2 101.87(7) 3_566 3_566 ?
O1 Co1 N2 78.13(7) . 3_566 ?
N2 Co1 N2 180.00(12) . 3_566 ?
C3 N1 N2 112.4(2) . . ?
C3 N1 H1 125.0 . . ?
N2 N1 H1 122.3 . . ?
C4 O1 Co1 116.65(15) . . ?
C3 C2 C1 104.9(2) . . ?
C3 C2 H2 127.6 . . ?
C1 C2 H2 127.6 . . ?
N1 N2 C1 105.1(2) . . ?
N1 N2 Co1 143.03(16) . . ?
C1 N2 Co1 111.83(16) . . ?
N1 C3 C2 107.1(2) . . ?
N1 C3 H3 126.5 . . ?
C2 C3 H3 126.5 . . ?
Co1 O3 H3B 121.3 . . ?
Co1 O3 H3A 125.3 . . ?
H3B O3 H3A 96.8 . . ?
O2 C4 O1 124.9(2) . . ?
O2 C4 C1 119.5(2) . 3_566 ?
O1 C4 C1 115.6(2) . 3_566 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 Co1 O1 C4 -86.81(19) 3_566 . . . ?
O3 Co1 O1 C4 93.19(19) . . . . ?
O1 Co1 O1 C4 61(100) 3_566 . . . ?
N2 Co1 O1 C4 -177.69(19) . . . . ?
N2 Co1 O1 C4 2.31(19) 3_566 . . . ?
N2 C1 C2 C3 0.3(3) . . . . ?
C4 C1 C2 C3 -177.0(3) 3_566 . . . ?
C3 N1 N2 C1 0.6(3) . . . . ?
C3 N1 N2 Co1 -177.8(2) . . . . ?
C2 C1 N2 N1 -0.5(3) . . . . ?
C4 C1 N2 N1 177.2(2) 3_566 . . . ?
C2 C1 N2 Co1 178.4(2) . . . . ?
C4 C1 N2 Co1 -3.9(3) 3_566 . . . ?
O3 Co1 N2 N1 -87.5(3) 3_566 . . . ?
O3 Co1 N2 N1 92.5(3) . . . . ?
O1 Co1 N2 N1 -178.4(3) 3_566 . . . ?
O1 Co1 N2 N1 1.6(3) . . . . ?
N2 Co1 N2 N1 -131(87) 3_566 . . . ?
O3 Co1 N2 C1 94.15(18) 3_566 . . . ?
O3 Co1 N2 C1 -85.85(18) . . . . ?
O1 Co1 N2 C1 3.25(18) 3_566 . . . ?
O1 Co1 N2 C1 -176.75(18) . . . . ?
N2 Co1 N2 C1 50(87) 3_566 . . . ?
N2 N1 C3 C2 -0.4(3) . . . . ?
C1 C2 C3 N1 0.0(3) . . . . ?
Co1 O1 C4 O2 179.9(2) . . . . ?
Co1 O1 C4 C1 -1.0(3) . . . 3_566 ?

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
O3 H3A O1 0.84 1.89 2.715(3) 164.3 3_666
N1 H1 O2 0.83 2.05 2.809(3) 152.2 2_655
O3 H3B O2 0.91 1.83 2.731(3) 167.6 4_566

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        28.97
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.083

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ni
_database_code_depnum_ccdc_archive 'CCDC 1032278'
#Added by publCIF



_audit_update_record             
;
2014-11-02 deposited with the CCDC.
2016-02-05 downloaded from the CCDC.
;


_symmetry_space_group_name_hall  '-P 2ybc'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H12 N2 Ni O8'
_chemical_formula_weight         298.89

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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   12.5491(8)
_cell_length_b                   7.1794(5)
_cell_length_c                   11.6227(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.091(6)
_cell_angle_gamma                90.00
_cell_volume                     1036.72(11)
_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       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.915
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    1.908
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           ?

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3718
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_sigmaI/netI    0.0719
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.28
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1821
_reflns_number_gt                1440
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0923P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1821
_refine_ls_number_parameters     154
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0607
_refine_ls_wR_factor_ref         0.1646
_refine_ls_wR_factor_gt          0.1528
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.017
_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
C1 C 0.8626(4) -0.0205(7) 0.7050(4) 0.0323(11) Uani 1 1 d . . .
C2 C 0.9463(4) -0.1446(8) 0.6933(4) 0.0390(12) Uani 1 1 d . . .
H2 H 0.9970 -0.1925 0.7519 0.047 Uiso 1 1 calc R . .
C3 C 0.9370(4) -0.1803(7) 0.5757(4) 0.0386(13) Uani 1 1 d . . .
H3 H 0.9814 -0.2577 0.5392 0.046 Uiso 1 1 calc R . .
C4 C 0.8112(4) -0.0725(8) 0.3988(3) 0.0351(12) Uani 1 1 d . . .
H4A H 0.8646 -0.1256 0.3558 0.042 Uiso 1 1 calc R . .
H4B H 0.8032 0.0578 0.3773 0.042 Uiso 1 1 calc R . .
C5 C 0.7034(4) -0.1711(6) 0.3606(4) 0.0337(12) Uani 1 1 d . . .
C6 C 0.8195(4) 0.0562(6) 0.8088(4) 0.0302(11) Uani 1 1 d . . .
N1 N 0.8522(3) -0.0833(6) 0.5231(3) 0.0342(10) Uani 1 1 d . . .
N2 N 0.8065(3) 0.0174(6) 0.6012(3) 0.0319(10) Uani 1 1 d . . .
Ni1 Ni 0.67582(5) 0.19056(8) 0.61421(5) 0.0311(3) Uani 1 1 d . . .
O1 O 0.6523(3) -0.2411(6) 0.4339(3) 0.0432(9) Uani 1 1 d . . .
O2 O 0.6781(3) -0.1733(5) 0.2522(3) 0.0430(10) Uani 1 1 d . . .
O3 O 0.8663(3) 0.0209(5) 0.9077(2) 0.0414(9) Uani 1 1 d . . .
O4 O 0.7340(3) 0.1514(5) 0.7851(3) 0.0365(8) Uani 1 1 d . . .
O5 O 0.5826(3) -0.0553(4) 0.6134(2) 0.0356(8) Uani 1 1 d D . .
H5A H 0.6108 -0.1009 0.5591 0.053 Uiso 1 1 d RD . .
H5B H 0.6063 -0.1244 0.6679 0.053 Uiso 1 1 d RD . .
O6 O 0.5512(3) 0.3438(5) 0.6662(3) 0.0447(9) Uani 1 1 d D . .
H6A H 0.5839 0.4456 0.6621 0.067 Uiso 1 1 d RD . .
H6B H 0.4875 0.3288 0.6323 0.067 Uiso 1 1 d RD . .
O7 O 0.7727(3) 0.4210(5) 0.6096(3) 0.0409(9) Uani 1 1 d D . .
H7A H 0.7536 0.5145 0.6445 0.061 Uiso 1 1 d RD . .
H7B H 0.7902 0.4496 0.5450 0.061 Uiso 1 1 d RD . .
O8 O 0.6169(3) 0.2221(6) 0.4441(3) 0.0486(11) Uani 1 1 d D . .
H8A H 0.6479 0.2944 0.4028 0.073 Uiso 1 1 d RD . .
H8B H 0.5590 0.1624 0.4233 0.073 Uiso 1 1 d RD . .

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
C1 0.032(2) 0.046(3) 0.021(2) 0.003(2) 0.0109(19) -0.007(2)
C2 0.038(3) 0.049(3) 0.030(3) 0.002(2) 0.005(2) 0.002(3)
C3 0.037(3) 0.046(3) 0.034(3) -0.002(2) 0.013(2) 0.006(2)
C4 0.037(3) 0.050(3) 0.022(2) -0.009(2) 0.0162(19) -0.004(2)
C5 0.038(3) 0.036(3) 0.028(3) -0.004(2) 0.008(2) 0.003(2)
C6 0.038(3) 0.030(3) 0.025(2) 0.0032(19) 0.0109(19) -0.005(2)
N1 0.034(2) 0.044(3) 0.0269(19) -0.0006(19) 0.0122(16) -0.0015(19)
N2 0.032(2) 0.041(2) 0.0254(19) -0.0037(18) 0.0126(16) 0.0034(19)
Ni1 0.0342(4) 0.0422(6) 0.0193(4) -0.0007(2) 0.0119(3) 0.0001(2)
O1 0.041(2) 0.065(2) 0.0279(19) -0.0074(18) 0.0182(15) -0.0111(19)
O2 0.052(2) 0.052(2) 0.0254(19) -0.0005(15) 0.0081(17) -0.0077(18)
O3 0.043(2) 0.058(2) 0.0239(17) -0.0009(16) 0.0071(14) 0.0022(18)
O4 0.040(2) 0.053(2) 0.0198(16) 0.0003(15) 0.0136(14) 0.0058(17)
O5 0.0399(19) 0.045(2) 0.0240(15) -0.0004(14) 0.0125(13) -0.0008(16)
O6 0.0359(19) 0.057(2) 0.043(2) -0.0106(18) 0.0112(16) 0.0011(18)
O7 0.051(2) 0.043(2) 0.0328(17) -0.0002(16) 0.0198(15) -0.0081(17)
O8 0.042(2) 0.082(3) 0.0224(18) 0.0062(18) 0.0075(15) -0.018(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
C1 N2 1.336(5) . ?
C1 C2 1.398(7) . ?
C1 C6 1.495(6) . ?
C2 C3 1.380(7) . ?
C2 H2 0.9300 . ?
C3 N1 1.344(6) . ?
C3 H3 0.9300 . ?
C4 N1 1.466(5) . ?
C4 C5 1.536(7) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 O1 1.242(6) . ?
C5 O2 1.255(6) . ?
C6 O3 1.242(5) . ?
C6 O4 1.269(6) . ?
N1 N2 1.350(5) . ?
N2 Ni1 2.080(4) . ?
Ni1 O8 2.024(3) . ?
Ni1 O4 2.037(3) . ?
Ni1 O7 2.058(3) . ?
Ni1 O6 2.070(4) . ?
Ni1 O5 2.117(3) . ?
O5 H5A 0.8338 . ?
O5 H5B 0.8256 . ?
O6 H6A 0.8433 . ?
O6 H6B 0.8463 . ?
O7 H7A 0.8362 . ?
O7 H7B 0.8375 . ?
O8 H8A 0.8394 . ?
O8 H8B 0.8492 . ?

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
N2 C1 C2 110.5(4) . . ?
N2 C1 C6 116.7(4) . . ?
C2 C1 C6 132.5(4) . . ?
C3 C2 C1 104.8(4) . . ?
C3 C2 H2 127.6 . . ?
C1 C2 H2 127.6 . . ?
N1 C3 C2 107.7(5) . . ?
N1 C3 H3 126.1 . . ?
C2 C3 H3 126.1 . . ?
N1 C4 C5 115.7(4) . . ?
N1 C4 H4A 108.4 . . ?
C5 C4 H4A 108.4 . . ?
N1 C4 H4B 108.4 . . ?
C5 C4 H4B 108.4 . . ?
H4A C4 H4B 107.4 . . ?
O1 C5 O2 127.0(5) . . ?
O1 C5 C4 120.4(4) . . ?
O2 C5 C4 112.6(4) . . ?
O3 C6 O4 125.9(4) . . ?
O3 C6 C1 119.6(4) . . ?
O4 C6 C1 114.5(4) . . ?
C3 N1 N2 110.9(4) . . ?
C3 N1 C4 128.4(4) . . ?
N2 N1 C4 120.7(4) . . ?
C1 N2 N1 106.1(4) . . ?
C1 N2 Ni1 112.1(3) . . ?
N1 N2 Ni1 141.5(3) . . ?
O8 Ni1 O4 178.46(15) . . ?
O8 Ni1 O7 91.18(14) . . ?
O4 Ni1 O7 90.24(13) . . ?
O8 Ni1 O6 92.19(15) . . ?
O4 Ni1 O6 88.32(14) . . ?
O7 Ni1 O6 93.08(14) . . ?
O8 Ni1 N2 100.33(15) . . ?
O4 Ni1 N2 79.07(14) . . ?
O7 Ni1 N2 90.23(15) . . ?
O6 Ni1 N2 166.98(14) . . ?
O8 Ni1 O5 87.91(13) . . ?
O4 Ni1 O5 90.64(13) . . ?
O7 Ni1 O5 176.58(13) . . ?
O6 Ni1 O5 90.25(13) . . ?
N2 Ni1 O5 86.70(14) . . ?
C6 O4 Ni1 117.5(3) . . ?
Ni1 O5 H5A 92.1 . . ?
Ni1 O5 H5B 111.0 . . ?
H5A O5 H5B 101.5 . . ?
Ni1 O6 H6A 92.9 . . ?
Ni1 O6 H6B 120.0 . . ?
H6A O6 H6B 121.3 . . ?
Ni1 O7 H7A 115.0 . . ?
Ni1 O7 H7B 116.8 . . ?
H7A O7 H7B 111.5 . . ?
Ni1 O8 H8A 119.6 . . ?
Ni1 O8 H8B 113.7 . . ?
H8A O8 H8B 126.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C1 C2 C3 -0.3(6) . . . . ?
C6 C1 C2 C3 172.0(5) . . . . ?
C1 C2 C3 N1 -0.5(6) . . . . ?
N1 C4 C5 O1 5.5(7) . . . . ?
N1 C4 C5 O2 -173.1(4) . . . . ?
N2 C1 C6 O3 177.8(4) . . . . ?
C2 C1 C6 O3 5.9(8) . . . . ?
N2 C1 C6 O4 -0.7(6) . . . . ?
C2 C1 C6 O4 -172.6(5) . . . . ?
C2 C3 N1 N2 1.1(6) . . . . ?
C2 C3 N1 C4 178.7(4) . . . . ?
C5 C4 N1 C3 109.1(5) . . . . ?
C5 C4 N1 N2 -73.4(6) . . . . ?
C2 C1 N2 N1 0.9(5) . . . . ?
C6 C1 N2 N1 -172.7(4) . . . . ?
C2 C1 N2 Ni1 176.9(3) . . . . ?
C6 C1 N2 Ni1 3.3(5) . . . . ?
C3 N1 N2 C1 -1.2(5) . . . . ?
C4 N1 N2 C1 -179.1(4) . . . . ?
C3 N1 N2 Ni1 -175.3(4) . . . . ?
C4 N1 N2 Ni1 6.9(7) . . . . ?
C1 N2 Ni1 O8 178.0(3) . . . . ?
N1 N2 Ni1 O8 -8.1(5) . . . . ?
C1 N2 Ni1 O4 -3.4(3) . . . . ?
N1 N2 Ni1 O4 170.4(5) . . . . ?
C1 N2 Ni1 O7 86.8(3) . . . . ?
N1 N2 Ni1 O7 -99.4(5) . . . . ?
C1 N2 Ni1 O6 -18.1(9) . . . . ?
N1 N2 Ni1 O6 155.8(6) . . . . ?
C1 N2 Ni1 O5 -94.7(3) . . . . ?
N1 N2 Ni1 O5 79.1(5) . . . . ?
O3 C6 O4 Ni1 179.1(4) . . . . ?
C1 C6 O4 Ni1 -2.4(5) . . . . ?
O8 Ni1 O4 C6 71(5) . . . . ?
O7 Ni1 O4 C6 -86.9(3) . . . . ?
O6 Ni1 O4 C6 -180.0(3) . . . . ?
N2 Ni1 O4 C6 3.3(3) . . . . ?
O5 Ni1 O4 C6 89.8(3) . . . . ?

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
O5 H5B O2 0.83 1.91 2.700(5) 160.9 4_556
O6 H6A O2 0.84 2.19 2.947(5) 148.5 4_566
O6 H6B O1 0.85 1.92 2.753(5) 167.8 3_656
O7 H7A O2 0.84 2.02 2.826(5) 160.4 4_566
O7 H7B O3 0.84 1.98 2.800(4) 164.8 4_565
O8 H8A O4 0.84 1.90 2.677(5) 153.6 4_565
O8 H8B O5 0.85 1.93 2.770(5) 171.7 3_656

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.987
_refine_diff_density_min         -1.147
_refine_diff_density_rms         0.132

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu
_database_code_depnum_ccdc_archive 'CCDC 1032279'
_audit_update_record             
;
2014-11-02 deposited with the CCDC.
2016-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H16 Cu2 N4 O12'
_chemical_formula_weight         535.37

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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                   13.0966(16)
_cell_length_b                   8.4245(10)
_cell_length_c                   16.766(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.2400(10)
_cell_angle_gamma                90.00
_cell_volume                     1756.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.024
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1080
_exptl_absorpt_coefficient_mu    2.499
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5992
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0173
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         24.99
_reflns_number_total             1542
_reflns_number_gt                1428
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0393P)²+2.2063P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1542
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0248
_refine_ls_R_factor_gt           0.0228
_refine_ls_wR_factor_ref         0.0626
_refine_ls_wR_factor_gt          0.0611
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_refine_ls_shift/su_max          0.002
_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 0.635098(19) 0.20763(3) 0.639022(16) 0.02411(12) Uani 1 1 d . . .
C1 C 0.57442(18) 0.3054(2) 0.47289(14) 0.0235(5) Uani 1 1 d . . .
C2 C 0.47690(17) 0.2254(3) 0.48243(14) 0.0225(5) Uani 1 1 d . . .
C3 C 0.37481(18) 0.1910(3) 0.42831(15) 0.0281(5) Uani 1 1 d . . .
H3 H 0.3468 0.2162 0.3716 0.034 Uiso 1 1 calc R . .
C4 C 0.32444(17) 0.1115(3) 0.47700(13) 0.0249(5) Uani 1 1 d . . .
H4 H 0.2544 0.0727 0.4592 0.030 Uiso 1 1 calc R . .
C5 C 0.37788(16) 0.0293(2) 0.62962(13) 0.0229(5) Uani 1 1 d . . .
H5A H 0.4335 -0.0490 0.6531 0.027 Uiso 1 1 calc R . .
H5B H 0.3091 -0.0249 0.6135 0.027 Uiso 1 1 calc R . .
N1 N 0.39463(13) 0.0997(2) 0.55537(11) 0.0209(4) Uani 1 1 d . . .
N2 N 0.48831(13) 0.1695(2) 0.55925(11) 0.0208(4) Uani 1 1 d . . .
O1 O 0.65579(13) 0.30414(19) 0.53913(10) 0.0299(4) Uani 1 1 d . . .
O2 O 0.57213(12) 0.3647(2) 0.40500(10) 0.0334(4) Uani 1 1 d . . .
O5 O 0.79127(12) 0.18700(19) 0.68708(10) 0.0307(4) Uani 1 1 d . . .
O6 O 0.61243(12) 0.46685(19) 0.68922(10) 0.0313(4) Uani 1 1 d . . .
C6 C 0.38002(15) 0.1529(3) 0.69625(13) 0.0218(4) Uani 1 1 d . . .
O3 O 0.38059(12) 0.09242(18) 0.76588(9) 0.0264(3) Uani 1 1 d . . .
O4 O 0.38114(14) 0.29494(18) 0.67936(11) 0.0335(4) Uani 1 1 d . . .
H6D H 0.5640 0.4975 0.6693 0.050 Uiso 1 1 d R . .
H6C H 0.6063 0.4287 0.7220 0.050 Uiso 1 1 d R . .
H5C H 0.8079 0.1351 0.7180 0.050 Uiso 1 1 d R . .
H5D H 0.8178 0.1692 0.6607 0.050 Uiso 1 1 d 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 0.01812(17) 0.03575(19) 0.01928(18) 0.00402(10) 0.00706(12) -0.00275(10)
C1 0.0235(11) 0.0246(11) 0.0256(12) 0.0028(8) 0.0124(9) 0.0041(8)
C2 0.0210(11) 0.0260(11) 0.0219(12) 0.0014(8) 0.0090(9) 0.0031(8)
C3 0.0250(12) 0.0387(13) 0.0196(12) 0.0006(9) 0.0053(9) 0.0026(9)
C4 0.0191(10) 0.0321(12) 0.0222(11) -0.0051(9) 0.0046(9) -0.0007(9)
C5 0.0263(11) 0.0246(11) 0.0207(11) -0.0029(9) 0.0117(9) -0.0070(9)
N1 0.0200(9) 0.0244(9) 0.0208(9) -0.0033(7) 0.0101(7) -0.0034(7)
N2 0.0190(9) 0.0246(9) 0.0203(9) -0.0002(7) 0.0084(7) -0.0015(7)
O1 0.0219(8) 0.0442(10) 0.0233(9) 0.0057(7) 0.0069(7) -0.0062(7)
O2 0.0284(8) 0.0473(10) 0.0287(9) 0.0151(8) 0.0149(7) 0.0063(7)
O5 0.0222(8) 0.0431(9) 0.0291(9) 0.0105(7) 0.0111(7) 0.0046(7)
O6 0.0315(8) 0.0334(9) 0.0280(9) 0.0052(7) 0.0076(7) 0.0025(7)
C6 0.0122(9) 0.0310(12) 0.0221(11) -0.0056(9) 0.0052(8) -0.0009(8)
O3 0.0269(8) 0.0351(8) 0.0204(8) -0.0040(6) 0.0123(6) -0.0019(7)
O4 0.0443(10) 0.0271(9) 0.0266(9) -0.0034(6) 0.0075(8) 0.0029(7)

_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 O3 1.9317(15) 2_656 ?
Cu1 O1 1.9555(16) . ?
Cu1 O5 1.9573(16) . ?
Cu1 N2 1.9946(17) . ?
Cu1 O6 2.3920(17) . ?
C1 O2 1.235(3) . ?
C1 O1 1.276(3) . ?
C1 C2 1.496(3) . ?
C2 N2 1.335(3) . ?
C2 C3 1.391(3) . ?
C3 C4 1.374(3) . ?
C3 H3 0.9300 . ?
C4 N1 1.351(3) . ?
C4 H4 0.9300 . ?
C5 N1 1.456(3) . ?
C5 C6 1.521(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
N1 N2 1.344(2) . ?
O5 H5C 0.6615 . ?
O5 H5D 0.6601 . ?
O6 H6D 0.6692 . ?
O6 H6C 0.6628 . ?
C6 O4 1.230(3) . ?
C6 O3 1.272(3) . ?
O3 Cu1 1.9317(15) 2_656 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Cu1 O1 174.22(7) 2_656 . ?
O3 Cu1 O5 89.02(6) 2_656 . ?
O1 Cu1 O5 88.99(7) . . ?
O3 Cu1 N2 98.24(7) 2_656 . ?
O1 Cu1 N2 81.69(7) . . ?
O5 Cu1 N2 157.73(7) . . ?
O3 Cu1 O6 96.39(6) 2_656 . ?
O1 Cu1 O6 89.29(6) . . ?
O5 Cu1 O6 99.50(6) . . ?
N2 Cu1 O6 100.56(6) . . ?
O2 C1 O1 125.3(2) . . ?
O2 C1 C2 120.4(2) . . ?
O1 C1 C2 114.30(19) . . ?
N2 C2 C3 110.48(19) . . ?
N2 C2 C1 114.87(18) . . ?
C3 C2 C1 134.6(2) . . ?
C4 C3 C2 104.9(2) . . ?
C4 C3 H3 127.6 . . ?
C2 C3 H3 127.6 . . ?
N1 C4 C3 107.86(19) . . ?
N1 C4 H4 126.1 . . ?
C3 C4 H4 126.1 . . ?
N1 C5 C6 112.09(17) . . ?
N1 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
N1 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
N2 N1 C4 110.35(17) . . ?
N2 N1 C5 121.10(17) . . ?
C4 N1 C5 128.51(17) . . ?
C2 N2 N1 106.44(17) . . ?
C2 N2 Cu1 112.54(14) . . ?
N1 N2 Cu1 140.96(14) . . ?
C1 O1 Cu1 116.55(14) . . ?
Cu1 O5 H5C 115.3 . . ?
Cu1 O5 H5D 116.5 . . ?
H5C O5 H5D 105.2 . . ?
Cu1 O6 H6D 112.3 . . ?
Cu1 O6 H6C 84.9 . . ?
H6D O6 H6C 105.1 . . ?
O4 C6 O3 127.2(2) . . ?
O4 C6 C5 119.69(19) . . ?
O3 C6 C5 113.15(18) . . ?
C6 O3 Cu1 125.77(14) . 2_656 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 N2 -178.34(19) . . . . ?
O1 C1 C2 N2 2.1(3) . . . . ?
O2 C1 C2 C3 3.6(4) . . . . ?
O1 C1 C2 C3 -176.0(2) . . . . ?
N2 C2 C3 C4 0.4(3) . . . . ?
C1 C2 C3 C4 178.5(2) . . . . ?
C2 C3 C4 N1 -0.5(2) . . . . ?
C3 C4 N1 N2 0.4(2) . . . . ?
C3 C4 N1 C5 178.25(19) . . . . ?
C6 C5 N1 N2 64.9(2) . . . . ?
C6 C5 N1 C4 -112.7(2) . . . . ?
C3 C2 N2 N1 -0.2(2) . . . . ?
C1 C2 N2 N1 -178.70(17) . . . . ?
C3 C2 N2 Cu1 177.78(14) . . . . ?
C1 C2 N2 Cu1 -0.8(2) . . . . ?
C4 N1 N2 C2 -0.2(2) . . . . ?
C5 N1 N2 C2 -178.19(18) . . . . ?
C4 N1 N2 Cu1 -177.12(17) . . . . ?
C5 N1 N2 Cu1 4.8(3) . . . . ?
O3 Cu1 N2 C2 -174.51(14) 2_656 . . . ?
O1 Cu1 N2 C2 -0.34(15) . . . . ?
O5 Cu1 N2 C2 -66.6(2) . . . . ?
O6 Cu1 N2 C2 87.36(15) . . . . ?
O3 Cu1 N2 N1 2.3(2) 2_656 . . . ?
O1 Cu1 N2 N1 176.5(2) . . . . ?
O5 Cu1 N2 N1 110.3(2) . . . . ?
O6 Cu1 N2 N1 -95.8(2) . . . . ?
O2 C1 O1 Cu1 178.06(17) . . . . ?
C2 C1 O1 Cu1 -2.4(2) . . . . ?
O3 Cu1 O1 C1 91.4(6) 2_656 . . . ?
O5 Cu1 O1 C1 161.32(16) . . . . ?
N2 Cu1 O1 C1 1.61(15) . . . . ?
O6 Cu1 O1 C1 -99.17(16) . . . . ?
N1 C5 C6 O4 9.1(3) . . . . ?
N1 C5 C6 O3 -170.78(16) . . . . ?
O4 C6 O3 Cu1 8.4(3) . . . 2_656 ?
C5 C6 O3 Cu1 -171.66(12) . . . 2_656 ?

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
O6 H6D O2 0.67 2.16 2.821(2) 167.3 5_666
O5 H5D O2 0.66 2.09 2.739(2) 168.4 7_656
O5 H5C O6 0.66 2.12 2.774(2) 169.4 4_646

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.072
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_co1
_database_code_depnum_ccdc_archive 'CCDC 1032280'
_audit_update_record             
;
2014-11-02 deposited with the CCDC.
2016-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H16 Co2 N4 O12'
_chemical_formula_weight         526.15

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           ?
_symmetry_space_group_name_H-M   ?

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                   14.7287(7)
_cell_length_b                   7.2556(4)
_cell_length_c                   16.8674(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.253(4)
_cell_angle_gamma                90.00
_cell_volume                     1794.97(15)
_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       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.947
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1064
_exptl_absorpt_coefficient_mu    1.925
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3344
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.13
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1584
_reflns_number_gt                1305
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0404P)²+0.3696P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1584
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0806
_refine_ls_wR_factor_gt          0.0745
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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 0.60942(15) 0.8391(3) 0.49310(12) 0.0209(5) Uani 1 1 d . . .
C2 C 0.67759(18) 0.9593(4) 0.52376(15) 0.0297(6) Uani 1 1 d . . .
H2 H 0.6935 1.0723 0.5030 0.036 Uiso 1 1 calc R . .
C3 C 0.71601(16) 0.8740(4) 0.59128(14) 0.0299(6) Uani 1 1 d . . .
H3 H 0.7629 0.9202 0.6263 0.036 Uiso 1 1 calc R . .
C4 C 0.68317(16) 0.5844(4) 0.66443(13) 0.0253(6) Uani 1 1 d . . .
H4A H 0.7468 0.5781 0.6849 0.030 Uiso 1 1 calc R . .
H4B H 0.6644 0.4622 0.6463 0.030 Uiso 1 1 calc R . .
C5 C 0.62622(16) 0.6431(4) 0.73141(13) 0.0244(6) Uani 1 1 d . . .
C6 C 0.54247(16) 0.8481(3) 0.42226(13) 0.0223(5) Uani 1 1 d . . .
Co1 Co 0.5000 1.00873(6) 0.2500 0.02224(17) Uani 1 2 d S . .
Co2 Co 0.5000 0.5000 0.5000 0.01841(16) Uani 1 2 d S . .
N1 N 0.67348(12) 0.7112(3) 0.59755(10) 0.0226(5) Uani 1 1 d . . .
N2 N 0.60693(12) 0.6871(3) 0.53810(10) 0.0203(5) Uani 1 1 d . . .
O1 O 0.61858(14) 0.5270(2) 0.78532(11) 0.0352(5) Uani 1 1 d . . .
O2 O 0.54447(13) 0.9854(2) 0.37663(10) 0.0284(5) Uani 1 1 d . . .
O3 O 0.48700(11) 0.7151(2) 0.41255(9) 0.0250(4) Uani 1 1 d . . .
O5 O 0.39975(13) 0.8166(3) 0.26914(10) 0.0366(5) Uani 1 1 d . . .
H5 H 0.4066 0.7808 0.3154 0.055 Uiso 1 1 calc R . .
O6 O 0.41786(12) 0.6475(2) 0.57141(10) 0.0284(4) Uani 1 1 d . . .
H6 H 0.4377 0.7526 0.5776 0.043 Uiso 1 1 calc R . .
H5W H 0.394(2) 0.694(5) 0.242(2) 0.085(13) Uiso 1 1 d . . .
H6W H 0.404(2) 0.597(5) 0.617(2) 0.073(11) Uiso 1 1 d . . .
O4 O 0.59498(14) 0.8006(3) 0.72765(11) 0.0442(5) Uani 1 1 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
C1 0.0269(13) 0.0206(14) 0.0160(11) 0.0000(10) 0.0060(10) -0.0013(11)
C2 0.0360(15) 0.0232(14) 0.0300(14) 0.0009(12) 0.0044(12) -0.0111(12)
C3 0.0313(14) 0.0300(15) 0.0275(12) -0.0041(12) -0.0017(11) -0.0123(12)
C4 0.0270(13) 0.0267(14) 0.0217(12) 0.0027(12) -0.0002(10) 0.0038(11)
C5 0.0280(13) 0.0226(14) 0.0220(12) -0.0016(11) -0.0010(10) 0.0005(11)
C6 0.0300(13) 0.0193(13) 0.0183(11) -0.0027(11) 0.0058(10) 0.0014(11)
Co1 0.0330(3) 0.0158(3) 0.0179(3) 0.000 0.0024(2) 0.000
Co2 0.0247(3) 0.0161(3) 0.0142(3) 0.00092(17) 0.00049(19) -0.00470(18)
N1 0.0255(11) 0.0249(12) 0.0171(9) 0.0012(9) -0.0003(8) -0.0049(9)
N2 0.0231(10) 0.0228(11) 0.0148(9) -0.0012(9) 0.0006(8) -0.0027(9)
O1 0.0547(13) 0.0319(11) 0.0201(9) 0.0052(8) 0.0087(9) 0.0045(9)
O2 0.0469(12) 0.0199(10) 0.0178(9) 0.0035(7) -0.0006(8) -0.0079(8)
O3 0.0335(9) 0.0218(9) 0.0187(8) 0.0029(7) -0.0031(7) -0.0083(8)
O5 0.0492(11) 0.0330(12) 0.0266(10) 0.0050(9) -0.0022(8) -0.0120(10)
O6 0.0389(10) 0.0202(10) 0.0273(9) -0.0018(9) 0.0091(8) -0.0069(8)
O4 0.0644(13) 0.0284(11) 0.0428(11) 0.0033(9) 0.0215(10) 0.0188(10)

_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
C1 N2 1.341(3) . ?
C1 C2 1.393(3) . ?
C1 C6 1.479(3) . ?
C2 C3 1.372(3) . ?
C2 H2 0.9300 . ?
C3 N1 1.346(3) . ?
C3 H3 0.9300 . ?
C4 N1 1.452(3) . ?
C4 C5 1.528(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 O4 1.231(3) . ?
C5 O1 1.252(3) . ?
C6 O2 1.260(3) . ?
C6 O3 1.266(3) . ?
Co1 O4 2.0271(19) 6_575 ?
Co1 O4 2.0271(19) 5_676 ?
Co1 O5 2.0772(18) . ?
Co1 O5 2.0772(18) 2_655 ?
Co1 O2 2.1827(17) 2_655 ?
Co1 O2 2.1827(17) . ?
Co2 O6 2.0799(16) 5_666 ?
Co2 O6 2.0799(16) . ?
Co2 N2 2.1334(18) . ?
Co2 N2 2.1334(18) 5_666 ?
Co2 O3 2.1437(15) . ?
Co2 O3 2.1437(15) 5_666 ?
N1 N2 1.348(2) . ?
O5 H5 0.8200 . ?
O5 H5W 1.00(4) . ?
O6 H6 0.8200 . ?
O6 H6W 0.89(4) . ?
O4 Co1 2.0271(19) 5_676 ?

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
N2 C1 C2 111.1(2) . . ?
N2 C1 C6 116.3(2) . . ?
C2 C1 C6 132.6(2) . . ?
C3 C2 C1 104.7(2) . . ?
C3 C2 H2 127.6 . . ?
C1 C2 H2 127.6 . . ?
N1 C3 C2 107.6(2) . . ?
N1 C3 H3 126.2 . . ?
C2 C3 H3 126.2 . . ?
N1 C4 C5 112.1(2) . . ?
N1 C4 H4A 109.2 . . ?
C5 C4 H4A 109.2 . . ?
N1 C4 H4B 109.2 . . ?
C5 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
O4 C5 O1 127.1(2) . . ?
O4 C5 C4 116.6(2) . . ?
O1 C5 C4 116.2(2) . . ?
O2 C6 O3 125.1(2) . . ?
O2 C6 C1 118.5(2) . . ?
O3 C6 C1 116.4(2) . . ?
O4 Co1 O4 93.94(12) 6_575 5_676 ?
O4 Co1 O5 177.87(7) 6_575 . ?
O4 Co1 O5 85.21(9) 5_676 . ?
O4 Co1 O5 85.21(9) 6_575 2_655 ?
O4 Co1 O5 177.87(7) 5_676 2_655 ?
O5 Co1 O5 95.70(12) . 2_655 ?
O4 Co1 O2 91.22(7) 6_575 2_655 ?
O4 Co1 O2 94.85(7) 5_676 2_655 ?
O5 Co1 O2 86.91(7) . 2_655 ?
O5 Co1 O2 87.12(7) 2_655 2_655 ?
O4 Co1 O2 94.85(7) 6_575 . ?
O4 Co1 O2 91.22(7) 5_676 . ?
O5 Co1 O2 87.12(7) . . ?
O5 Co1 O2 86.91(7) 2_655 . ?
O2 Co1 O2 171.10(8) 2_655 . ?
O6 Co2 O6 180.00(8) 5_666 . ?
O6 Co2 N2 92.82(7) 5_666 . ?
O6 Co2 N2 87.18(7) . . ?
O6 Co2 N2 87.18(7) 5_666 5_666 ?
O6 Co2 N2 92.82(7) . 5_666 ?
N2 Co2 N2 180.00(8) . 5_666 ?
O6 Co2 O3 89.77(7) 5_666 . ?
O6 Co2 O3 90.23(7) . . ?
N2 Co2 O3 76.17(6) . . ?
N2 Co2 O3 103.83(6) 5_666 . ?
O6 Co2 O3 90.23(7) 5_666 5_666 ?
O6 Co2 O3 89.77(7) . 5_666 ?
N2 Co2 O3 103.83(6) . 5_666 ?
N2 Co2 O3 76.17(6) 5_666 5_666 ?
O3 Co2 O3 180.000(1) . 5_666 ?
C3 N1 N2 111.55(18) . . ?
C3 N1 C4 127.12(19) . . ?
N2 N1 C4 120.60(19) . . ?
C1 N2 N1 105.00(18) . . ?
C1 N2 Co2 114.24(14) . . ?
N1 N2 Co2 140.63(15) . . ?
C6 O2 Co1 129.58(14) . . ?
C6 O3 Co2 116.77(14) . . ?
Co1 O5 H5 109.5 . . ?
Co1 O5 H5W 124(2) . . ?
H5 O5 H5W 98.8 . . ?
Co2 O6 H6 109.5 . . ?
Co2 O6 H6W 118(2) . . ?
H6 O6 H6W 112.1 . . ?
C5 O4 Co1 152.22(18) . 5_676 ?

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
O5 H5 O3 0.82 1.99 2.734(2) 150.7 .
O6 H6 O2 0.82 2.06 2.843(2) 159.8 5_676
O5 H5W O1 1.00(4) 1.67(4) 2.662(3) 169(3) 5_666
O6 H6W O1 0.89(4) 1.78(4) 2.670(2) 172(3) 2_656
C3 H3 O1 0.93 2.32 3.252(3) 178.3 4_656

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.066
