# 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 2018

####################################################################### 
# 
# 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_t
_database_code_depnum_ccdc_archive 'CCDC 1819593'
_audit_update_record             
;
2018-04-02 deposited with the CCDC.
2018-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H7 Co N O6'
_chemical_formula_weight         260.07

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'
Co Co 0.3494 0.9721 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   9.873(8)
_cell_length_b                   11.983(10)
_cell_length_c                   7.366(8)
_cell_angle_alpha                90
_cell_angle_beta                 105.172(9)
_cell_angle_gamma                90
_cell_volume                     841.1(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2392
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      30.58

_exptl_crystal_description       plates
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.054
_exptl_crystal_F_000             524
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    2.049
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.685
_exptl_absorpt_correction_T_max  0.885
_exptl_absorpt_process_details   'Face indexing'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2092
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.731
_diffrn_reflns_theta_max         25.480
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             784
_reflns_number_gt                771
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0230P)²+1.6471P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         784
_refine_ls_number_parameters     76
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0230
_refine_ls_R_factor_gt           0.0227
_refine_ls_wR_factor_ref         0.0601
_refine_ls_wR_factor_gt          0.0599
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_restrained_S_all      1.174
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 1.0000 0.66134(3) 0.2500 0.01574(15) Uani 1 2 d S T P . .
O1 O 0.86213(15) 0.52337(13) 0.2583(2) 0.0265(4) Uani 1 1 d . . . . .
O2 O 0.74787(17) 0.68053(12) 0.2009(3) 0.0288(4) Uani 1 1 d . . . . .
O3 O 0.96284(17) 0.67009(12) -0.0396(2) 0.0246(4) Uani 1 1 d D . . . .
N1 N 0.5000 0.34421(18) 0.2500 0.0162(5) Uani 1 2 d S T P . .
C1 C 0.7500(2) 0.57780(17) 0.2313(3) 0.0182(4) Uani 1 1 d . . . . .
C2 C 0.61824(19) 0.51827(16) 0.2377(3) 0.0161(4) Uani 1 1 d . . . . .
C3 C 0.61231(19) 0.40255(17) 0.2334(3) 0.0168(4) Uani 1 1 d . . . . .
H3 H 0.6900 0.3634 0.2182 0.020 Uiso 1 1 calc R U . . .
C4 C 0.5000 0.5772(2) 0.2500 0.0170(6) Uani 1 2 d S T P . .
H4 H 0.5000 0.6549 0.2500 0.020 Uiso 1 2 calc R U P . .
H3B H 0.901(2) 0.7192(16) -0.087(3) 0.020 Uiso 1 1 d D U . . .
H3A H 0.940(2) 0.6088(12) -0.096(3) 0.020 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O3 2.071(3) . ?
Co1 O3 2.071(3) 2_755 ?
Co1 O1 2.152(2) . ?
Co1 O1 2.152(2) 2_755 ?
Co1 N1 2.191(3) 3 ?
O1 C1 1.255(3) . ?
O2 C1 1.250(3) . ?
O3 H3B 0.853(10) . ?
O3 H3A 0.846(10) . ?
N1 C3 1.343(2) 2_655 ?
N1 C3 1.343(2) . ?
N1 Co1 2.191(3) 3_445 ?
C1 C2 1.495(3) . ?
C2 C4 1.388(2) . ?
C2 C3 1.388(3) . ?
C3 H3 0.9300 . ?
C4 C2 1.388(2) 2_655 ?
C4 H4 0.9300 . ?

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 Co1 O3 174.19(8) . 2_755 ?
O3 Co1 O1 97.19(6) . . ?
O3 Co1 O1 87.29(6) 2_755 . ?
O3 Co1 O1 87.29(6) . 2_755 ?
O3 Co1 O1 97.19(6) 2_755 2_755 ?
O1 Co1 O1 79.64(10) . 2_755 ?
O3 Co1 N1 87.10(4) . 3 ?
O3 Co1 N1 87.10(4) 2_755 3 ?
O1 Co1 N1 140.18(5) . 3 ?
O1 Co1 N1 140.18(5) 2_755 3 ?
C1 O1 Co1 97.74(14) . . ?
Co1 O3 H3B 112.0(17) . . ?
Co1 O3 H3A 114.7(17) . . ?
H3B O3 H3A 109(2) . . ?
C3 N1 C3 117.3(2) 2_655 . ?
C3 N1 Co1 121.36(12) 2_655 3_445 ?
C3 N1 Co1 121.36(12) . 3_445 ?
O2 C1 O1 120.82(18) . . ?
O2 C1 C2 120.11(18) . . ?
O1 C1 C2 119.06(18) . . ?
C4 C2 C3 118.62(18) . . ?
C4 C2 C1 120.85(19) . . ?
C3 C2 C1 120.53(17) . . ?
N1 C3 C2 123.28(18) . . ?
N1 C3 H3 118.4 . . ?
C2 C3 H3 118.4 . . ?
C2 C4 C2 118.8(3) 2_655 . ?
C2 C4 H4 120.6 2_655 . ?
C2 C4 H4 120.6 . . ?

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
Co1 O1 C1 O2 3.6(2) . . . . ?
Co1 O1 C1 C2 -175.84(15) . . . . ?
O2 C1 C2 C4 -13.7(3) . . . . ?
O1 C1 C2 C4 165.77(17) . . . . ?
O2 C1 C2 C3 167.01(19) . . . . ?
O1 C1 C2 C3 -13.6(3) . . . . ?
C3 N1 C3 C2 1.76(14) 2_655 . . . ?
Co1 N1 C3 C2 -178.24(14) 3_445 . . . ?
C4 C2 C3 N1 -3.5(3) . . . . ?
C1 C2 C3 N1 175.90(16) . . . . ?
C3 C2 C4 C2 1.61(13) . . . 2_655 ?
C1 C2 C4 C2 -177.7(2) . . . 2_655 ?

_refine_diff_density_max         0.296
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.085

####################################################################### 
# 
# 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_t_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1819594'
_audit_update_record             
;
2018-04-02 deposited with the CCDC.
2018-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 Co N3 O6'
_chemical_formula_weight         379.21

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'
Co Co 0.3494 0.9721 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.804(2)
_cell_length_b                   9.8015(17)
_cell_length_c                   12.078(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.057(3)
_cell_angle_gamma                90
_cell_volume                     1514.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2636
_cell_measurement_theta_min      4.2580
_cell_measurement_theta_max      48.6740

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.663
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    1.171
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.685
_exptl_absorpt_correction_T_max  0.885
_exptl_absorpt_process_details   'Face indexing'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8955
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.618
_diffrn_reflns_theta_max         28.311
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3638
_reflns_number_gt                2651
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0325P)²+0.8490P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3638
_refine_ls_number_parameters     229
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0862
_refine_ls_wR_factor_gt          0.0765
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.64298(3) 0.47974(3) 0.83789(3) 0.02324(10) Uani 1 1 d . . . . .
O1 O 0.63257(17) 0.30571(19) 0.30013(14) 0.0400(5) Uani 1 1 d . . . . .
O2 O 0.61574(15) 0.17467(16) 0.44719(15) 0.0325(4) Uani 1 1 d . . . . .
O3 O 0.64814(18) 0.81174(18) 0.36062(14) 0.0434(5) Uani 1 1 d . . . . .
O4 O 0.66258(16) 0.89199(17) 0.52914(15) 0.0372(5) Uani 1 1 d . . . . .
O5 O 0.47927(16) 0.4967(2) 0.82625(17) 0.0437(5) Uani 1 1 d D . . . .
H5A H 0.455(2) 0.570(2) 0.797(2) 0.052 Uiso 1 1 d D U . . .
H5B H 0.439(2) 0.473(3) 0.878(2) 0.052 Uiso 1 1 d D U . . .
O6 O 0.7897(2) 0.4734(4) 0.1950(2) 0.0848(10) Uani 1 1 d D . . . .
H6A H 0.753(3) 0.536(4) 0.161(3) 0.102 Uiso 1 1 d D U . . .
H6B H 0.748(3) 0.414(4) 0.223(4) 0.102 Uiso 1 1 d D U . . .
N1 N 0.80255(18) 0.4416(2) 0.84973(17) 0.0308(5) Uani 1 1 d . . . . .
N2 N 0.95084(19) 0.3666(2) 0.9239(2) 0.0382(6) Uani 1 1 d . . . . .
N3 N 0.63913(16) 0.50141(18) 0.66190(15) 0.0223(4) Uani 1 1 d . . . . .
C1 C 0.8790(2) 0.4489(3) 0.7734(2) 0.0443(7) Uani 1 1 d . . . . .
H1 H 0.8693 0.4816 0.7015 0.053 Uiso 1 1 calc R U . . .
C2 C 0.9701(3) 0.4018(3) 0.8174(3) 0.0495(8) Uani 1 1 d . . . . .
H2 H 1.0334 0.3948 0.7823 0.059 Uiso 1 1 calc R U . . .
C3 C 0.8496(2) 0.3920(3) 0.9399(2) 0.0343(6) Uani 1 1 d . . . . .
H3 H 0.8168 0.3767 1.0063 0.041 Uiso 1 1 calc R U . . .
C4 C 1.0211(3) 0.2954(3) 1.0018(3) 0.0502(9) Uani 1 1 d . . . . .
H4A H 1.0079 0.3266 1.0762 0.060 Uiso 1 1 calc R U . . .
H4B H 1.0926 0.3189 0.9859 0.060 Uiso 1 1 calc R U . . .
C5 C 1.0092(2) 0.1421(3) 0.9976(2) 0.0336(6) Uani 1 1 d . . . . .
C6 C 1.0790(2) 0.0639(3) 1.0605(2) 0.0365(6) Uani 1 1 d . . . . .
H6 H 1.1326 0.1063 1.1016 0.044 Uiso 1 1 calc R U . . .
C7 C 0.9303(2) 0.0771(3) 0.9372(2) 0.0412(7) Uani 1 1 d . . . . .
H7 H 0.8828 0.1284 0.8946 0.049 Uiso 1 1 calc R U . . .
C8 C 0.63150(19) 0.3964(2) 0.59083(18) 0.0226(5) Uani 1 1 d . . . . .
H8 H 0.6269 0.3087 0.6196 0.027 Uiso 1 1 calc R U . . .
C9 C 0.63008(19) 0.4120(2) 0.47697(18) 0.0215(5) Uani 1 1 d . . . . .
C10 C 0.63629(19) 0.5427(2) 0.43418(18) 0.0220(5) Uani 1 1 d . . . . .
H10 H 0.6349 0.5567 0.3580 0.026 Uiso 1 1 calc R U . . .
C11 C 0.64461(19) 0.6523(2) 0.50642(18) 0.0203(5) Uani 1 1 d . . . . .
C12 C 0.64540(19) 0.6277(2) 0.61865(18) 0.0227(5) Uani 1 1 d . . . . .
H12 H 0.6505 0.7016 0.6668 0.027 Uiso 1 1 calc R U . . .
C13 C 0.6250(2) 0.2890(2) 0.4019(2) 0.0255(5) Uani 1 1 d . . . . .
C14 C 0.6525(2) 0.7955(2) 0.46321(19) 0.0253(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O2 2.0463(17) 4_566 ?
Co1 O3 2.0630(18) 4_576 ?
Co1 N1 2.077(2) . ?
Co1 O5 2.102(2) . ?
Co1 N3 2.1349(19) . ?
O1 C13 1.247(3) . ?
O2 C13 1.255(3) . ?
O2 Co1 2.0463(16) 4_565 ?
O3 C14 1.249(3) . ?
O3 Co1 2.0630(18) 4_575 ?
O4 C14 1.240(3) . ?
O5 H5A 0.856(10) . ?
O5 H5B 0.851(10) . ?
O6 H6A 0.867(10) . ?
O6 H6B 0.864(10) . ?
N1 C3 1.319(3) . ?
N1 C1 1.370(3) . ?
N2 C3 1.341(4) . ?
N2 C2 1.362(4) . ?
N2 C4 1.456(4) . ?
N3 C8 1.341(3) . ?
N3 C12 1.347(3) . ?
C1 C2 1.346(4) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 C5 1.511(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C7 1.381(4) . ?
C5 C6 1.383(4) . ?
C6 C7 1.388(4) 3_757 ?
C6 H6 0.9300 . ?
C7 C6 1.388(4) 3_757 ?
C7 H7 0.9300 . ?
C8 C9 1.383(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.384(3) . ?
C9 C13 1.509(3) . ?
C10 C11 1.386(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(3) . ?
C11 C14 1.502(3) . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Co1 O3 130.71(7) 4_566 4_576 ?
O2 Co1 N1 90.72(8) 4_566 . ?
O3 Co1 N1 98.18(9) 4_576 . ?
O2 Co1 O5 84.78(8) 4_566 . ?
O3 Co1 O5 87.58(9) 4_576 . ?
N1 Co1 O5 174.16(9) . . ?
O2 Co1 N3 135.84(7) 4_566 . ?
O3 Co1 N3 91.91(7) 4_576 . ?
N1 Co1 N3 94.24(8) . . ?
O5 Co1 N3 86.46(8) . . ?
C13 O2 Co1 110.99(15) . 4_565 ?
C14 O3 Co1 104.96(15) . 4_575 ?
Co1 O5 H5A 116(2) . . ?
Co1 O5 H5B 124(2) . . ?
H5A O5 H5B 108(3) . . ?
H6A O6 H6B 110(5) . . ?
C3 N1 C1 105.0(2) . . ?
C3 N1 Co1 122.86(19) . . ?
C1 N1 Co1 131.98(19) . . ?
C3 N2 C2 107.3(2) . . ?
C3 N2 C4 125.0(3) . . ?
C2 N2 C4 127.1(3) . . ?
C8 N3 C12 117.43(19) . . ?
C8 N3 Co1 124.01(14) . . ?
C12 N3 Co1 118.56(15) . . ?
C2 C1 N1 110.2(3) . . ?
C2 C1 H1 124.9 . . ?
N1 C1 H1 124.9 . . ?
C1 C2 N2 106.0(3) . . ?
C1 C2 H2 127.0 . . ?
N2 C2 H2 127.0 . . ?
N1 C3 N2 111.4(2) . . ?
N1 C3 H3 124.3 . . ?
N2 C3 H3 124.3 . . ?
N2 C4 C5 113.3(2) . . ?
N2 C4 H4A 108.9 . . ?
C5 C4 H4A 108.9 . . ?
N2 C4 H4B 108.9 . . ?
C5 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
C7 C5 C6 118.7(3) . . ?
C7 C5 C4 123.2(3) . . ?
C6 C5 C4 118.1(2) . . ?
C5 C6 C7 120.6(3) . 3_757 ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 3_757 . ?
C5 C7 C6 120.7(3) . 3_757 ?
C5 C7 H7 119.6 . . ?
C6 C7 H7 119.6 3_757 . ?
N3 C8 C9 123.3(2) . . ?
N3 C8 H8 118.3 . . ?
C9 C8 H8 118.3 . . ?
C8 C9 C10 118.3(2) . . ?
C8 C9 C13 120.5(2) . . ?
C10 C9 C13 121.1(2) . . ?
C9 C10 C11 119.1(2) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C12 C11 C10 118.8(2) . . ?
C12 C11 C14 120.5(2) . . ?
C10 C11 C14 120.69(19) . . ?
N3 C12 C11 123.0(2) . . ?
N3 C12 H12 118.5 . . ?
C11 C12 H12 118.5 . . ?
O1 C13 O2 124.0(2) . . ?
O1 C13 C9 119.0(2) . . ?
O2 C13 C9 117.0(2) . . ?
O4 C14 O3 122.7(2) . . ?
O4 C14 C11 119.8(2) . . ?
O3 C14 C11 117.5(2) . . ?

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
C3 N1 C1 C2 1.0(3) . . . . ?
Co1 N1 C1 C2 -174.2(2) . . . . ?
N1 C1 C2 N2 -1.0(4) . . . . ?
C3 N2 C2 C1 0.6(3) . . . . ?
C4 N2 C2 C1 172.0(3) . . . . ?
C1 N1 C3 N2 -0.7(3) . . . . ?
Co1 N1 C3 N2 175.11(17) . . . . ?
C2 N2 C3 N1 0.1(3) . . . . ?
C4 N2 C3 N1 -171.6(2) . . . . ?
C3 N2 C4 C5 79.8(4) . . . . ?
C2 N2 C4 C5 -90.3(4) . . . . ?
N2 C4 C5 C7 -8.4(4) . . . . ?
N2 C4 C5 C6 173.9(3) . . . . ?
C7 C5 C6 C7 0.0(5) . . . 3_757 ?
C4 C5 C6 C7 177.9(3) . . . 3_757 ?
C6 C5 C7 C6 0.0(5) . . . 3_757 ?
C4 C5 C7 C6 -177.7(3) . . . 3_757 ?
C12 N3 C8 C9 0.2(4) . . . . ?
Co1 N3 C8 C9 -179.38(18) . . . . ?
N3 C8 C9 C10 -0.4(4) . . . . ?
N3 C8 C9 C13 178.0(2) . . . . ?
C8 C9 C10 C11 0.6(4) . . . . ?
C13 C9 C10 C11 -177.7(2) . . . . ?
C9 C10 C11 C12 -0.6(4) . . . . ?
C9 C10 C11 C14 179.4(2) . . . . ?
C8 N3 C12 C11 -0.2(4) . . . . ?
Co1 N3 C12 C11 179.36(18) . . . . ?
C10 C11 C12 N3 0.4(4) . . . . ?
C14 C11 C12 N3 -179.6(2) . . . . ?
Co1 O2 C13 O1 10.9(3) 4_565 . . . ?
Co1 O2 C13 C9 -167.27(17) 4_565 . . . ?
C8 C9 C13 O1 -174.1(2) . . . . ?
C10 C9 C13 O1 4.2(4) . . . . ?
C8 C9 C13 O2 4.2(4) . . . . ?
C10 C9 C13 O2 -177.6(2) . . . . ?
Co1 O3 C14 O4 -6.6(3) 4_575 . . . ?
Co1 O3 C14 C11 173.07(18) 4_575 . . . ?
C12 C11 C14 O4 1.9(4) . . . . ?
C10 C11 C14 O4 -178.2(2) . . . . ?
C12 C11 C14 O3 -177.8(2) . . . . ?
C10 C11 C14 O3 2.1(4) . . . . ?

_refine_diff_density_max         0.391
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.068

