# 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 2015

####################################################################### 
# 
# 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_comaags
_database_code_depnum_ccdc_archive 'CCDC 917228'
_audit_update_record             
;
2012-12-27 deposited with the CCDC.
2015-10-27 downloaded from the CCDC.
;
#TrackingRef 'web_deposit_cif_file_0_R.Selvakumar_1356606571.comaags.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H22 Co N8 O10'
_chemical_formula_weight         449.27

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   6.9244(12)
_cell_length_b                   7.3583(12)
_cell_length_c                   9.5353(16)
_cell_angle_alpha                105.537(3)
_cell_angle_beta                 102.545(3)
_cell_angle_gamma                110.219(3)
_cell_volume                     412.65(12)
_cell_formula_units_Z            1
_cell_measurement_temperature    203(2)
_cell_measurement_reflns_used    2345
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      32.23

_exptl_crystal_description       chunk
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.808
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             233
_exptl_absorpt_coefficient_mu    1.114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7681
_exptl_absorpt_correction_T_max  0.8419
_exptl_absorpt_process_details   'Bruker Sadabs'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      203(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5131
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         32.26
_reflns_number_total             2679
_reflns_number_gt                2465
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0780P)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    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2679
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0925
_refine_ls_wR_factor_gt          0.0891
_refine_ls_goodness_of_fit_ref   0.885
_refine_ls_restrained_S_all      0.885
_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
Co Co 0.5000 0.5000 0.5000 0.01613(9) Uani 1 2 d S . .
O1 O 0.39677(17) 0.64354(16) 0.36047(11) 0.02146(19) Uani 1 1 d . . .
C1 C 0.3000(2) 0.76094(19) 0.38181(13) 0.0175(2) Uani 1 1 d . . .
N1 N 0.8876(2) 0.7230(3) -0.03297(16) 0.0313(3) Uani 1 1 d . . .
H1NA H 0.847(4) 0.602(4) -0.096(3) 0.045(6) Uiso 1 1 d . . .
O2 O 0.36006(16) 0.61310(16) 0.64961(11) 0.02120(19) Uani 1 1 d . . .
C2 C 0.1906(2) 0.7773(2) 0.50341(15) 0.0199(2) Uani 1 1 d . . .
H2A H 0.223(3) 0.924(3) 0.552(3) 0.037(6) Uiso 1 1 d . . .
H2B H 0.039(4) 0.689(3) 0.449(3) 0.034(5) Uiso 1 1 d . . .
N2 N 0.7051(2) 0.7710(2) -0.04768(14) 0.0260(2) Uani 1 1 d . . .
H2N H 0.621(4) 0.740(3) -0.140(3) 0.033(5) Uiso 1 1 d . . .
O3 O 0.2808(2) 0.86532(19) 0.29981(13) 0.0334(3) Uani 1 1 d . . .
C3 C 0.24360(19) 0.71227(19) 0.64026(14) 0.0170(2) Uani 1 1 d . . .
N3 N 0.7096(2) 0.7420(2) 0.18763(14) 0.0265(2) Uani 1 1 d . . .
H3NA H 0.823(3) 0.731(3) 0.191(2) 0.028(5) Uiso 1 1 d . . .
H3NB H 0.651(4) 0.716(4) 0.243(3) 0.041(6) Uiso 1 1 d . . .
O4 O 0.16259(17) 0.76090(17) 0.74192(11) 0.0233(2) Uani 1 1 d . . .
N4 N 0.4182(2) 0.7697(2) 0.03731(15) 0.0263(2) Uani 1 1 d . . .
H4NA H 0.358(3) 0.768(3) -0.043(2) 0.027(5) Uiso 1 1 d . . .
H4NB H 0.375(4) 0.785(4) 0.115(3) 0.044(6) Uiso 1 1 d . . .
C4 C 0.6085(2) 0.7586(2) 0.05980(14) 0.0207(2) Uani 1 1 d . . .
O5 O 0.21835(18) 0.21867(17) 0.37243(15) 0.0319(3) Uani 1 1 d . . .
H5OB H 0.214(4) 0.110(4) 0.352(3) 0.049(7) Uiso 1 1 d . . .
H5O H 0.110(4) 0.211(4) 0.336(3) 0.041(6) Uiso 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
Co 0.01902(13) 0.01955(13) 0.01808(13) 0.00979(9) 0.00944(9) 0.01352(10)
O1 0.0304(5) 0.0277(5) 0.0209(4) 0.0139(4) 0.0142(4) 0.0219(4)
C1 0.0212(5) 0.0197(5) 0.0153(5) 0.0068(4) 0.0065(4) 0.0125(4)
N1 0.0254(6) 0.0388(7) 0.0293(6) 0.0085(6) 0.0115(5) 0.0152(6)
O2 0.0255(4) 0.0306(5) 0.0201(4) 0.0131(4) 0.0123(4) 0.0205(4)
C2 0.0228(6) 0.0252(6) 0.0225(6) 0.0130(5) 0.0121(5) 0.0163(5)
N2 0.0255(6) 0.0378(7) 0.0183(5) 0.0113(5) 0.0097(4) 0.0154(5)
O3 0.0611(8) 0.0449(6) 0.0284(5) 0.0259(5) 0.0280(5) 0.0439(6)
C3 0.0153(5) 0.0188(5) 0.0187(5) 0.0068(4) 0.0065(4) 0.0089(4)
N3 0.0349(7) 0.0309(6) 0.0208(5) 0.0127(5) 0.0112(5) 0.0185(5)
O4 0.0266(5) 0.0353(5) 0.0204(4) 0.0126(4) 0.0131(4) 0.0223(4)
N4 0.0279(6) 0.0348(6) 0.0207(5) 0.0119(5) 0.0117(5) 0.0155(5)
C4 0.0246(6) 0.0188(5) 0.0174(5) 0.0057(4) 0.0077(4) 0.0084(4)
O5 0.0191(5) 0.0204(5) 0.0534(7) 0.0099(5) 0.0060(5) 0.0124(4)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co O2 2.0466(9) . ?
Co O2 2.0467(9) 2_666 ?
Co O1 2.0636(9) . ?
Co O1 2.0636(9) 2_666 ?
Co O5 2.0972(12) . ?
Co O5 2.0972(12) 2_666 ?
O1 C1 1.2657(15) . ?
C1 O3 1.2514(15) . ?
C1 C2 1.5175(18) . ?
N1 N2 1.4143(18) . ?
N1 H1NA 0.86(3) . ?
N1 H1NA 0.84(3) . ?
O2 C3 1.2653(14) . ?
C2 C3 1.5212(18) . ?
C2 H2A 0.97(2) . ?
C2 H2B 0.95(2) . ?
N2 C4 1.3459(17) . ?
N2 H2N 0.87(2) . ?
C3 O4 1.2535(15) . ?
N3 C4 1.3264(18) . ?
N3 H3NA 0.81(2) . ?
N3 H3NB 0.76(3) . ?
N4 C4 1.3227(19) . ?
N4 H4NA 0.79(2) . ?
N4 H4NB 0.85(2) . ?
O5 H5OB 0.76(3) . ?
O5 H5O 0.73(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 Co O2 180.000(1) . 2_666 ?
O2 Co O1 89.08(4) . . ?
O2 Co O1 90.92(4) 2_666 . ?
O2 Co O1 90.92(4) . 2_666 ?
O2 Co O1 89.08(4) 2_666 2_666 ?
O1 Co O1 180.0 . 2_666 ?
O2 Co O5 93.88(5) . . ?
O2 Co O5 86.12(5) 2_666 . ?
O1 Co O5 91.58(5) . . ?
O1 Co O5 88.42(5) 2_666 . ?
O2 Co O5 86.12(5) . 2_666 ?
O2 Co O5 93.88(5) 2_666 2_666 ?
O1 Co O5 88.42(5) . 2_666 ?
O1 Co O5 91.58(5) 2_666 2_666 ?
O5 Co O5 180.00(6) . 2_666 ?
C1 O1 Co 129.66(8) . . ?
O3 C1 O1 122.11(11) . . ?
O3 C1 C2 115.45(11) . . ?
O1 C1 C2 122.39(11) . . ?
N2 N1 H1NA 103.6(17) . . ?
N2 N1 H1NA 108.6(17) . . ?
H1NA N1 H1NA 119(2) . . ?
C3 O2 Co 131.33(8) . . ?
C1 C2 C3 123.25(11) . . ?
C1 C2 H2A 107.0(13) . . ?
C3 C2 H2A 103.7(13) . . ?
C1 C2 H2B 105.3(13) . . ?
C3 C2 H2B 104.1(13) . . ?
H2A C2 H2B 113.9(17) . . ?
C4 N2 N1 117.24(12) . . ?
C4 N2 H2N 116.8(14) . . ?
N1 N2 H2N 117.5(14) . . ?
O4 C3 O2 122.24(11) . . ?
O4 C3 C2 115.82(11) . . ?
O2 C3 C2 121.94(11) . . ?
C4 N3 H3NA 115.5(14) . . ?
C4 N3 H3NB 121.0(19) . . ?
H3NA N3 H3NB 122(2) . . ?
C4 N4 H4NA 118.7(14) . . ?
C4 N4 H4NB 115.8(16) . . ?
H4NA N4 H4NB 125(2) . . ?
N4 C4 N3 121.70(13) . . ?
N4 C4 N2 119.09(12) . . ?
N3 C4 N2 119.18(13) . . ?
Co O5 H5OB 126(2) . . ?
Co O5 H5O 124.6(19) . . ?
H5OB O5 H5O 109(3) . . ?

_diffrn_measured_fraction_theta_max 0.912
_diffrn_reflns_theta_full        32.26
_diffrn_measured_fraction_theta_full 0.912
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.071
####################################################################### 
# 
# 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_nimaags
_database_code_depnum_ccdc_archive 'CCDC 917229'
_audit_update_record             
;
2012-12-27 deposited with the CCDC.
2015-10-27 downloaded from the CCDC.
;
#TrackingRef 'web_deposit_cif_file_1_R.Selvakumar_1356606571.nimaags.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H22 N8 Ni O10'
_chemical_formula_weight         449.05

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   6.881(4)
_cell_length_b                   7.283(4)
_cell_length_c                   9.541(5)
_cell_angle_alpha                105.601(10)
_cell_angle_beta                 102.526(10)
_cell_angle_gamma                109.834(10)
_cell_volume                     407.3(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    203(2)
_cell_measurement_reflns_used    1064
_cell_measurement_theta_min      0.00
_cell_measurement_theta_max      0.00

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.831
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             234
_exptl_absorpt_coefficient_mu    1.266
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7769
_exptl_absorpt_correction_T_max  0.8629
_exptl_absorpt_process_details   'Bruker Sadabs'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      203(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5014
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_sigmaI/netI    0.0889
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         32.23
_reflns_number_total             2604
_reflns_number_gt                1932
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0780P)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    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2604
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0667
_refine_ls_wR_factor_ref         0.1637
_refine_ls_wR_factor_gt          0.1499
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_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
Ni Ni 0.5000 0.5000 0.5000 0.0183(2) Uani 1 2 d S . .
O1 O 0.4024(4) 0.6439(4) 0.3636(3) 0.0223(5) Uani 1 1 d . . .
C1 C 0.3013(5) 0.7585(5) 0.3832(3) 0.0187(6) Uani 1 1 d . . .
N1 N 0.8909(6) 0.7209(7) -0.0328(4) 0.0307(7) Uani 1 1 d . . .
H1NA H 0.986(8) 0.814(8) -0.041(5) 0.032(13) Uiso 1 1 d . . .
H1NB H 0.859(7) 0.610(7) -0.094(5) 0.021(11) Uiso 1 1 d . . .
O2 O 0.3620(4) 0.6072(4) 0.6493(3) 0.0234(5) Uani 1 1 d . . .
C2 C 0.1957(6) 0.7789(6) 0.5073(4) 0.0213(7) Uani 1 1 d . . .
H2A H 0.238(7) 0.941(7) 0.552(5) 0.030(11) Uiso 1 1 d . . .
H2B H 0.028(9) 0.687(8) 0.451(6) 0.043(13) Uiso 1 1 d . . .
N2 N 0.7084(6) 0.7687(6) -0.0467(4) 0.0276(7) Uani 1 1 d . . .
H2N H 0.638(9) 0.740(9) -0.116(6) 0.046(16) Uiso 1 1 d . . .
O3 O 0.2759(5) 0.8588(5) 0.2990(3) 0.0328(7) Uani 1 1 d . . .
C3 C 0.2444(5) 0.7074(5) 0.6413(4) 0.0189(6) Uani 1 1 d . . .
N3 N 0.7159(6) 0.7444(5) 0.1896(3) 0.0270(7) Uani 1 1 d . . .
H3NA H 0.822(7) 0.725(7) 0.190(5) 0.021(11) Uiso 1 1 d . . .
H3NB H 0.645(7) 0.708(7) 0.244(5) 0.028(11) Uiso 1 1 d . . .
O4 O 0.1606(4) 0.7523(4) 0.7412(3) 0.0258(5) Uani 1 1 d . . .
N4 N 0.4220(6) 0.7673(6) 0.0392(4) 0.0278(7) Uani 1 1 d . . .
H4NA H 0.368(9) 0.781(9) 0.094(7) 0.049(17) Uiso 1 1 d . . .
H4NB H 0.357(9) 0.775(8) -0.045(6) 0.047(14) Uiso 1 1 d . . .
C4 C 0.6122(6) 0.7584(5) 0.0611(4) 0.0216(7) Uani 1 1 d . . .
O5 O 0.2191(5) 0.2215(5) 0.3727(4) 0.0354(7) Uani 1 1 d . . .
H5OA H 0.224(9) 0.112(9) 0.360(6) 0.043(14) Uiso 1 1 d . . .
H5OB H 0.093(10) 0.229(9) 0.333(7) 0.064(18) Uiso 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
Ni 0.0218(3) 0.0231(3) 0.0132(3) 0.0112(2) 0.0043(2) 0.0107(3)
O1 0.0321(14) 0.0276(13) 0.0174(11) 0.0143(10) 0.0103(10) 0.0184(11)
C1 0.0222(16) 0.0210(16) 0.0108(13) 0.0071(12) 0.0014(12) 0.0084(14)
N1 0.0282(18) 0.038(2) 0.0228(16) 0.0082(16) 0.0076(14) 0.0130(17)
O2 0.0288(13) 0.0329(14) 0.0161(11) 0.0126(10) 0.0078(10) 0.0189(12)
C2 0.0258(17) 0.0270(18) 0.0187(15) 0.0138(14) 0.0087(14) 0.0150(15)
N2 0.0263(16) 0.043(2) 0.0133(13) 0.0135(14) 0.0051(13) 0.0129(15)
O3 0.0569(19) 0.0446(16) 0.0233(12) 0.0247(12) 0.0208(13) 0.0379(15)
C3 0.0169(15) 0.0211(16) 0.0134(13) 0.0059(12) 0.0005(12) 0.0055(13)
N3 0.0370(19) 0.0335(18) 0.0161(13) 0.0136(13) 0.0097(14) 0.0177(16)
O4 0.0317(14) 0.0404(15) 0.0172(11) 0.0156(11) 0.0119(11) 0.0228(12)
N4 0.0295(17) 0.0382(19) 0.0174(14) 0.0129(14) 0.0086(14) 0.0140(16)
C4 0.0273(17) 0.0178(15) 0.0140(14) 0.0055(12) 0.0038(13) 0.0053(14)
O5 0.0214(14) 0.0226(14) 0.0531(19) 0.0106(13) 0.0006(13) 0.0092(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
Ni O2 2.008(2) 2_666 ?
Ni O2 2.008(2) . ?
Ni O1 2.019(2) . ?
Ni O1 2.019(2) 2_666 ?
Ni O5 2.079(3) . ?
Ni O5 2.079(3) 2_666 ?
O1 C1 1.257(4) . ?
C1 O3 1.246(4) . ?
C1 C2 1.518(4) . ?
N1 N2 1.402(5) . ?
N1 H1NA 0.81(5) . ?
N1 H1NB 0.78(4) . ?
O2 C3 1.264(4) . ?
C2 C3 1.520(4) . ?
C2 H2A 1.05(4) . ?
C2 H2B 1.04(5) . ?
N2 C4 1.344(4) . ?
N2 H2N 0.66(6) . ?
C3 O4 1.244(4) . ?
N3 C4 1.326(4) . ?
N3 H3NA 0.79(4) . ?
N3 H3NB 0.83(5) . ?
N4 C4 1.306(5) . ?
N4 H4NA 0.71(6) . ?
N4 H4NB 0.85(6) . ?
O5 H5OA 0.79(6) . ?
O5 H5OB 0.89(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 Ni O2 179.999(1) 2_666 . ?
O2 Ni O1 88.99(10) 2_666 . ?
O2 Ni O1 91.01(10) . . ?
O2 Ni O1 91.01(10) 2_666 2_666 ?
O2 Ni O1 88.99(10) . 2_666 ?
O1 Ni O1 179.999(1) . 2_666 ?
O2 Ni O5 86.70(12) 2_666 . ?
O2 Ni O5 93.30(13) . . ?
O1 Ni O5 91.51(12) . . ?
O1 Ni O5 88.49(12) 2_666 . ?
O2 Ni O5 93.30(12) 2_666 2_666 ?
O2 Ni O5 86.70(12) . 2_666 ?
O1 Ni O5 88.49(12) . 2_666 ?
O1 Ni O5 91.51(12) 2_666 2_666 ?
O5 Ni O5 180.0 . 2_666 ?
C1 O1 Ni 129.2(2) . . ?
O3 C1 O1 122.1(3) . . ?
O3 C1 C2 115.3(3) . . ?
O1 C1 C2 122.6(3) . . ?
N2 N1 H1NA 107(3) . . ?
N2 N1 H1NB 111(3) . . ?
H1NA N1 H1NB 113(5) . . ?
C3 O2 Ni 130.5(2) . . ?
C1 C2 C3 123.6(3) . . ?
C1 C2 H2A 103(2) . . ?
C3 C2 H2A 109(2) . . ?
C1 C2 H2B 106(3) . . ?
C3 C2 H2B 102(3) . . ?
H2A C2 H2B 114(3) . . ?
C4 N2 N1 117.8(3) . . ?
C4 N2 H2N 113(5) . . ?
N1 N2 H2N 119(5) . . ?
O4 C3 O2 122.4(3) . . ?
O4 C3 C2 116.0(3) . . ?
O2 C3 C2 121.6(3) . . ?
C4 N3 H3NA 115(3) . . ?
C4 N3 H3NB 118(3) . . ?
H3NA N3 H3NB 121(4) . . ?
C4 N4 H4NA 128(5) . . ?
C4 N4 H4NB 120(3) . . ?
H4NA N4 H4NB 112(6) . . ?
N4 C4 N3 121.5(3) . . ?
N4 C4 N2 119.6(3) . . ?
N3 C4 N2 118.9(4) . . ?
Ni O5 H5OA 121(4) . . ?
Ni O5 H5OB 119(4) . . ?
H5OA O5 H5OB 121(6) . . ?

_diffrn_measured_fraction_theta_max 0.902
_diffrn_reflns_theta_full        32.23
_diffrn_measured_fraction_theta_full 0.902
_refine_diff_density_max         2.400
_refine_diff_density_min         -1.288
_refine_diff_density_rms         0.165


####################################################################### 
# 
# 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_conis
_database_code_depnum_ccdc_archive 'CCDC 1046628'
_audit_update_record             
;
2015-02-01 deposited with the CCDC.
2015-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H22 Co0.50 N8 Ni0.50 O10'
_chemical_formula_weight         446.13

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   6.9096(10)
_cell_length_b                   7.3355(10)
_cell_length_c                   9.5299(13)
_cell_angle_alpha                105.577(2)
_cell_angle_beta                 102.494(2)
_cell_angle_gamma                110.156(2)
_cell_volume                     410.52(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    203(2)
_cell_measurement_reflns_used    3320
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      32.22

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.805
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             231
_exptl_absorpt_coefficient_mu    1.188
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      203(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5106
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         32.24
_reflns_number_total             2655
_reflns_number_gt                2543
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0780P)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         2655
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0914
_refine_ls_wR_factor_gt          0.0888
_refine_ls_goodness_of_fit_ref   0.944
_refine_ls_restrained_S_all      0.944
_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
Co Co 0.5000 0.5000 0.5000 0.01540(9) Uani 0.50 2 d SP . .
Ni Ni 0.5000 0.5000 0.5000 0.01540(9) Uani 0.50 2 d SP . .
O1 O 0.39898(16) 0.64368(15) 0.36155(10) 0.02065(17) Uani 1 1 d . . .
N1 N 0.8889(2) 0.7224(2) -0.03317(15) 0.0295(2) Uani 1 1 d . . .
H1NB H 0.978(4) 0.820(4) -0.048(3) 0.043(6) Uiso 1 1 d . . .
H1NA H 0.850(4) 0.598(4) -0.097(3) 0.050(7) Uiso 1 1 d . . .
C1 C 0.30094(18) 0.76071(18) 0.38271(12) 0.0166(2) Uani 1 1 d . . .
C2 C 0.1924(2) 0.77773(19) 0.50500(14) 0.0190(2) Uani 1 1 d . . .
H2A H 0.227(3) 0.927(3) 0.554(3) 0.034(5) Uiso 1 1 d . . .
H2B H 0.035(3) 0.683(3) 0.449(2) 0.030(5) Uiso 1 1 d . . .
N2 N 0.70570(19) 0.7697(2) -0.04786(13) 0.0247(2) Uani 1 1 d . . .
H2N H 0.619(4) 0.740(3) -0.134(3) 0.036(5) Uiso 1 1 d . . .
O2 O 0.36045(15) 0.61061(15) 0.64972(10) 0.02105(18) Uani 1 1 d . . .
O3 O 0.2791(2) 0.86331(18) 0.29940(12) 0.0319(2) Uani 1 1 d . . .
C3 C 0.24426(17) 0.71045(17) 0.64059(13) 0.01636(19) Uani 1 1 d . . .
N3 N 0.7125(2) 0.74306(19) 0.18866(13) 0.0255(2) Uani 1 1 d . . .
H3NA H 0.825(4) 0.727(3) 0.190(2) 0.030(5) Uiso 1 1 d . . .
H3NB H 0.652(4) 0.719(4) 0.243(3) 0.041(6) Uiso 1 1 d . . .
O4 O 0.16209(16) 0.75825(16) 0.74197(11) 0.02285(18) Uani 1 1 d . . .
N4 N 0.4195(2) 0.7690(2) 0.03807(14) 0.0251(2) Uani 1 1 d . . .
H4NA H 0.359(3) 0.772(3) -0.040(2) 0.024(4) Uiso 1 1 d . . .
H4NB H 0.380(4) 0.787(4) 0.111(3) 0.039(6) Uiso 1 1 d . . .
C4 C 0.6099(2) 0.75862(18) 0.06038(13) 0.0199(2) Uani 1 1 d . . .
O5 O 0.21861(17) 0.21959(16) 0.37260(15) 0.0319(2) Uani 1 1 d . . .
H5A H 0.217(5) 0.120(5) 0.360(3) 0.055(8) Uiso 1 1 d . . .
H5B H 0.109(4) 0.206(4) 0.338(3) 0.038(6) Uiso 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
Co 0.01801(12) 0.01893(12) 0.01669(12) 0.00911(8) 0.00905(8) 0.01246(9)
Ni 0.01801(12) 0.01893(12) 0.01669(12) 0.00911(8) 0.00905(8) 0.01246(9)
O1 0.0288(4) 0.0261(4) 0.0206(4) 0.0136(3) 0.0143(3) 0.0197(4)
N1 0.0241(5) 0.0366(6) 0.0271(6) 0.0079(5) 0.0110(4) 0.0137(5)
C1 0.0198(5) 0.0195(5) 0.0133(4) 0.0062(4) 0.0062(4) 0.0111(4)
C2 0.0221(5) 0.0248(5) 0.0201(5) 0.0123(4) 0.0116(4) 0.0156(4)
N2 0.0232(5) 0.0363(6) 0.0169(5) 0.0108(4) 0.0090(4) 0.0134(4)
O2 0.0262(4) 0.0304(4) 0.0192(4) 0.0129(3) 0.0129(3) 0.0204(4)
O3 0.0579(7) 0.0440(6) 0.0261(5) 0.0247(4) 0.0264(5) 0.0418(6)
C3 0.0151(4) 0.0193(4) 0.0162(4) 0.0063(4) 0.0064(4) 0.0088(4)
N3 0.0349(6) 0.0296(5) 0.0190(5) 0.0124(4) 0.0114(4) 0.0179(5)
O4 0.0261(4) 0.0351(5) 0.0191(4) 0.0125(3) 0.0133(3) 0.0211(4)
N4 0.0258(5) 0.0347(6) 0.0191(5) 0.0109(4) 0.0112(4) 0.0147(4)
C4 0.0236(5) 0.0185(5) 0.0162(5) 0.0059(4) 0.0073(4) 0.0074(4)
O5 0.0185(4) 0.0200(4) 0.0530(7) 0.0086(4) 0.0051(4) 0.0118(4)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co O2 2.0339(9) 2_666 ?
Co O2 2.0339(9) . ?
Co O1 2.0480(9) . ?
Co O1 2.0480(9) 2_666 ?
Co O5 2.0897(11) . ?
Co O5 2.0897(11) 2_666 ?
O1 C1 1.2663(14) . ?
N1 N2 1.4125(17) . ?
N1 H1NB 0.84(3) . ?
N1 H1NA 0.86(3) . ?
C1 O3 1.2518(14) . ?
C1 C2 1.5169(16) . ?
C2 C3 1.5185(16) . ?
C2 H2A 0.98(2) . ?
C2 H2B 0.99(2) . ?
N2 C4 1.3460(16) . ?
N2 H2N 0.83(2) . ?
O2 C3 1.2640(13) . ?
C3 O4 1.2536(14) . ?
N3 C4 1.3288(16) . ?
N3 H3NA 0.82(2) . ?
N3 H3NB 0.75(3) . ?
N4 C4 1.3189(17) . ?
N4 H4NA 0.79(2) . ?
N4 H4NB 0.79(2) . ?
O5 H5A 0.70(3) . ?
O5 H5B 0.72(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 Co O2 180.0 2_666 . ?
O2 Co O1 90.20(4) 2_666 . ?
O2 Co O1 89.80(4) . . ?
O2 Co O1 89.80(4) 2_666 2_666 ?
O2 Co O1 90.20(4) . 2_666 ?
O1 Co O1 180.00(4) . 2_666 ?
O2 Co O5 86.40(4) 2_666 . ?
O2 Co O5 93.60(5) . . ?
O1 Co O5 91.62(5) . . ?
O1 Co O5 88.38(5) 2_666 . ?
O2 Co O5 93.60(4) 2_666 2_666 ?
O2 Co O5 86.40(4) . 2_666 ?
O1 Co O5 88.38(5) . 2_666 ?
O1 Co O5 91.62(5) 2_666 2_666 ?
O5 Co O5 180.00(8) . 2_666 ?
C1 O1 Co 129.46(8) . . ?
N2 N1 H1NB 102.2(17) . . ?
N2 N1 H1NA 109.5(18) . . ?
H1NB N1 H1NA 116(2) . . ?
O3 C1 O1 122.06(10) . . ?
O3 C1 C2 115.47(11) . . ?
O1 C1 C2 122.41(10) . . ?
C1 C2 C3 123.25(10) . . ?
C1 C2 H2A 106.6(13) . . ?
C3 C2 H2A 104.4(13) . . ?
C1 C2 H2B 105.3(12) . . ?
C3 C2 H2B 102.2(12) . . ?
H2A C2 H2B 115.6(17) . . ?
C4 N2 N1 117.31(11) . . ?
C4 N2 H2N 113.3(15) . . ?
N1 N2 H2N 121.0(15) . . ?
C3 O2 Co 130.80(8) . . ?
O4 C3 O2 122.19(11) . . ?
O4 C3 C2 115.59(10) . . ?
O2 C3 C2 122.21(10) . . ?
C4 N3 H3NA 115.8(14) . . ?
C4 N3 H3NB 119.7(19) . . ?
H3NA N3 H3NB 122(2) . . ?
C4 N4 H4NA 120.2(14) . . ?
C4 N4 H4NB 116.5(17) . . ?
H4NA N4 H4NB 123(2) . . ?
N3 C4 N4 121.77(12) . . ?
N3 C4 N2 119.10(12) . . ?
N4 C4 N2 119.10(11) . . ?
Co O5 H5A 123(2) . . ?
Co O5 H5B 127.7(19) . . ?
H5A O5 H5B 109(3) . . ?

_diffrn_measured_fraction_theta_max 0.911
_diffrn_reflns_theta_full        32.24
_diffrn_measured_fraction_theta_full 0.911
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.079
