# 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_Zn
_database_code_depnum_ccdc_archive 'CCDC 1402544'
_audit_update_record             
;
2015-10-07 deposited with the CCDC.
2015-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H7 N5 O6 Zn'
_chemical_formula_weight         298.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.1736(8)
_cell_length_b                   10.0387(10)
_cell_length_c                   11.0871(11)
_cell_angle_alpha                90
_cell_angle_beta                 106.5680(10)
_cell_angle_gamma                90
_cell_volume                     871.95(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1441
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      26.52

_exptl_crystal_description       prismatic
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.274
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    2.851
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.566
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   'Bruker SADABS (Bruker, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Axs APEX automatic diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5284
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.600
_diffrn_reflns_theta_max         28.106
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.925
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1978
_reflns_number_gt                1646
_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 smart'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0491P)²+0.0978P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1978
_refine_ls_number_parameters     182
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.0946
_refine_ls_wR_factor_gt          0.0897
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.071
_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
Zn1 Zn 0.23537(4) 0.13506(3) 0.25370(3) 0.00903(14) Uani 1 1 d . . . . .
C1 C 0.2348(4) -0.0376(3) 0.0381(3) 0.0106(6) Uani 1 1 d . . . . .
C2 C 0.1934(4) -0.1636(3) 0.0808(3) 0.0115(7) Uani 1 1 d . . . . .
C3 C 0.2773(4) -0.2363(3) 0.0041(3) 0.0109(7) Uani 1 1 d . . . . .
C4 C 0.3173(4) -0.1067(3) -0.0487(3) 0.0120(7) Uani 1 1 d . . . . .
C5 C 0.0318(4) -0.1411(3) 0.2327(3) 0.0078(6) Uani 1 1 d . . . . .
N1 N 0.0580(3) -0.0126(3) 0.2633(2) 0.0091(5) Uani 1 1 d . . . . .
N2 N -0.0416(3) 0.0122(3) 0.3404(3) 0.0112(6) Uani 1 1 d . . . . .
N3 N -0.1214(3) -0.0955(3) 0.3550(2) 0.0108(6) Uani 1 1 d . . . . .
N4 N -0.0785(3) -0.1956(3) 0.2876(2) 0.0096(6) Uani 1 1 d . . . . .
O1 O 0.2144(3) 0.0822(2) 0.0627(2) 0.0110(5) Uani 1 1 d . . . . .
N5 N 0.1102(3) -0.2131(3) 0.1604(3) 0.0113(6) Uani 1 1 d D . . . .
O1W O 0.2771(3) 0.1809(2) 0.4499(2) 0.0120(5) Uani 1 1 d D . . . .
O3 O 0.3053(3) -0.3568(2) -0.0086(2) 0.0116(5) Uani 1 1 d . . . . .
O2W O 0.4505(3) 0.2396(2) 0.2480(2) 0.0124(5) Uani 1 1 d D . . . .
O4 O 0.3846(3) -0.0715(2) -0.1288(2) 0.0134(5) Uani 1 1 d . . . . .
O3W O 0.4365(3) -0.0153(2) 0.3280(2) 0.0117(5) Uani 1 1 d D . . . .
H11W H 0.234(6) 0.136(4) 0.500(4) 0.054(16) Uiso 1 1 d D . . . .
H12W H 0.271(5) 0.259(3) 0.482(4) 0.042(14) Uiso 1 1 d D . . . .
H21W H 0.453(8) 0.325(2) 0.234(6) 0.08(2) Uiso 1 1 d D . . . .
H31W H 0.400(4) -0.059(3) 0.382(3) 0.018(10) Uiso 1 1 d D . . . .
H5 H 0.084(6) -0.295(2) 0.151(4) 0.045(15) Uiso 1 1 d D . . . .
H22W H 0.500(5) 0.194(4) 0.201(4) 0.035(12) Uiso 1 1 d D . . . .
H32W H 0.529(4) 0.028(4) 0.367(4) 0.035(12) Uiso 1 1 d 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
Zn1 O2W 2.065(2) . ?
Zn1 N1 2.097(3) . ?
Zn1 N4 2.100(3) 2 ?
Zn1 O1 2.142(2) . ?
Zn1 O1W 2.153(2) . ?
Zn1 O3W 2.210(2) . ?
C1 O1 1.255(4) . ?
C1 C2 1.425(4) . ?
C1 C4 1.494(4) . ?
C2 N5 1.354(4) . ?
C2 C3 1.434(4) . ?
C3 O3 1.246(4) . ?
C3 C4 1.501(4) . ?
C4 O4 1.223(4) . ?
C5 N1 1.336(4) . ?
C5 N4 1.340(4) . ?
C5 N5 1.366(4) . ?
N1 N2 1.362(3) . ?
N2 N3 1.297(4) . ?
N3 N4 1.357(4) . ?
N4 Zn1 2.100(3) 2_545 ?
N5 H5 0.851(19) . ?
O1W H11W 0.87(2) . ?
O1W H12W 0.87(2) . ?
O2W H21W 0.88(2) . ?
O2W H22W 0.88(2) . ?
O3W H31W 0.87(2) . ?
O3W H32W 0.87(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2W Zn1 N1 165.50(9) . . ?
O2W Zn1 N4 93.11(9) . 2 ?
N1 Zn1 N4 101.26(10) . 2 ?
O2W Zn1 O1 85.66(9) . . ?
N1 Zn1 O1 90.77(9) . . ?
N4 Zn1 O1 96.50(9) 2 . ?
O2W Zn1 O1W 91.79(9) . . ?
N1 Zn1 O1W 90.73(9) . . ?
N4 Zn1 O1W 87.60(10) 2 . ?
O1 Zn1 O1W 175.28(8) . . ?
O2W Zn1 O3W 79.00(9) . . ?
N1 Zn1 O3W 87.13(9) . . ?
N4 Zn1 O3W 167.71(10) 2 . ?
O1 Zn1 O3W 92.32(8) . . ?
O1W Zn1 O3W 83.29(9) . . ?
O1 C1 C2 136.1(3) . . ?
O1 C1 C4 134.2(3) . . ?
C2 C1 C4 89.7(3) . . ?
N5 C2 C1 138.9(3) . . ?
N5 C2 C3 127.9(3) . . ?
C1 C2 C3 93.2(3) . . ?
O3 C3 C2 134.0(3) . . ?
O3 C3 C4 136.9(3) . . ?
C2 C3 C4 89.1(2) . . ?
O4 C4 C1 135.5(3) . . ?
O4 C4 C3 136.6(3) . . ?
C1 C4 C3 87.9(2) . . ?
N1 C5 N4 111.0(3) . . ?
N1 C5 N5 126.3(3) . . ?
N4 C5 N5 122.6(3) . . ?
C5 N1 N2 104.8(2) . . ?
C5 N1 Zn1 137.1(2) . . ?
N2 N1 Zn1 116.62(19) . . ?
N3 N2 N1 109.7(2) . . ?
N2 N3 N4 109.3(2) . . ?
C5 N4 N3 105.2(2) . . ?
C5 N4 Zn1 132.8(2) . 2_545 ?
N3 N4 Zn1 118.80(19) . 2_545 ?
C1 O1 Zn1 118.3(2) . . ?
C2 N5 C5 126.5(3) . . ?
C2 N5 H5 116(3) . . ?
C5 N5 H5 116(3) . . ?
Zn1 O1W H11W 124(3) . . ?
Zn1 O1W H12W 127(3) . . ?
H11W O1W H12W 97(4) . . ?
Zn1 O2W H21W 125(4) . . ?
Zn1 O2W H22W 107(3) . . ?
H21W O2W H22W 112(4) . . ?
Zn1 O3W H31W 104(2) . . ?
Zn1 O3W H32W 107(3) . . ?
H31W O3W H32W 109(4) . . ?

_refine_diff_density_max         0.999
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.132

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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 1402545'
_audit_update_record             
;
2015-10-07 deposited with the CCDC.
2015-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H7 Co N5 O6'
_chemical_formula_weight         292.09

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'

_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                   8.193(2)
_cell_length_b                   10.046(3)
_cell_length_c                   10.966(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.514(4)
_cell_angle_gamma                90
_cell_volume                     865.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1095
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      24.75

_exptl_crystal_description       prismatic
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.242
_exptl_crystal_F_000             588
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    2.018
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.566
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   'Bruker SADABS (Bruker, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Axs APEX automatic diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5280
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.593
_diffrn_reflns_theta_max         28.178
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1930
_reflns_number_gt                1499
_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 smart'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0539P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1930
_refine_ls_number_parameters     182
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1045
_refine_ls_wR_factor_gt          0.0962
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.036
_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 0.23536(6) 0.13296(4) 0.25368(4) 0.00965(17) Uani 1 1 d . . . . .
C1 C 0.2355(4) -0.0384(3) 0.0384(3) 0.0116(7) Uani 1 1 d . . . . .
C2 C 0.1935(4) -0.1637(3) 0.0818(3) 0.0102(7) Uani 1 1 d . . . . .
C3 C 0.2781(4) -0.2371(3) 0.0046(3) 0.0116(7) Uani 1 1 d . . . . .
C4 C 0.3179(4) -0.1079(3) -0.0479(3) 0.0116(7) Uani 1 1 d . . . . .
C5 C 0.0309(4) -0.1406(3) 0.2352(3) 0.0106(7) Uani 1 1 d . . . . .
N1 N 0.0549(3) -0.0125(3) 0.2643(3) 0.0088(6) Uani 1 1 d . . . . .
N2 N -0.0449(3) 0.0126(3) 0.3411(3) 0.0121(6) Uani 1 1 d . . . . .
N3 N -0.1242(4) -0.0952(3) 0.3563(3) 0.0122(6) Uani 1 1 d . . . . .
N4 N -0.0806(3) -0.1960(3) 0.2889(3) 0.0110(6) Uani 1 1 d . . . . .
O1 O 0.2146(3) 0.0823(2) 0.0637(2) 0.0111(5) Uani 1 1 d . . . . .
N5 N 0.1100(4) -0.2134(3) 0.1619(3) 0.0106(6) Uani 1 1 d D . . . .
O1W O 0.2730(3) 0.1813(3) 0.4476(2) 0.0131(5) Uani 1 1 d D . . . .
O3 O 0.3065(3) -0.3571(2) -0.0073(2) 0.0122(5) Uani 1 1 d . . . . .
O2W O 0.4472(3) 0.2429(2) 0.2481(2) 0.0118(5) Uani 1 1 d D . . . .
O4 O 0.3863(3) -0.0729(2) -0.1291(2) 0.0147(5) Uani 1 1 d . . . . .
O3W O 0.4336(3) -0.0148(2) 0.3268(2) 0.0126(5) Uani 1 1 d D . . . .
H11W H 0.236(5) 0.132(3) 0.498(3) 0.024(12) Uiso 1 1 d D . . . .
H12W H 0.277(5) 0.261(2) 0.477(4) 0.029(12) Uiso 1 1 d D . . . .
H21W H 0.442(6) 0.328(2) 0.233(4) 0.048(15) Uiso 1 1 d D . . . .
H31W H 0.402(4) -0.057(3) 0.385(3) 0.014(10) Uiso 1 1 d D . . . .
H5 H 0.089(5) -0.295(2) 0.161(4) 0.017(11) Uiso 1 1 d D . . . .
H22W H 0.496(5) 0.205(4) 0.195(4) 0.046(15) Uiso 1 1 d D . . . .
H32W H 0.519(4) 0.031(3) 0.370(3) 0.024(12) Uiso 1 1 d 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 O2W 2.073(2) . ?
Co1 O1 2.104(2) . ?
Co1 N1 2.105(3) . ?
Co1 N4 2.107(3) 2 ?
Co1 O1W 2.117(3) . ?
Co1 O3W 2.179(3) . ?
C1 O1 1.266(4) . ?
C1 C2 1.422(5) . ?
C1 C4 1.484(5) . ?
C2 N5 1.353(4) . ?
C2 C3 1.441(4) . ?
C3 O3 1.241(4) . ?
C3 C4 1.494(5) . ?
C4 O4 1.230(4) . ?
C5 N1 1.327(4) . ?
C5 N4 1.341(4) . ?
C5 N5 1.377(4) . ?
N1 N2 1.354(4) . ?
N2 N3 1.298(4) . ?
N3 N4 1.360(4) . ?
N4 Co1 2.107(3) 2_545 ?
N5 H5 0.838(19) . ?
O1W H11W 0.86(2) . ?
O1W H12W 0.86(2) . ?
O2W H21W 0.87(2) . ?
O2W H22W 0.88(2) . ?
O3W H31W 0.87(2) . ?
O3W H32W 0.86(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2W Co1 O1 86.11(9) . . ?
O2W Co1 N1 168.10(10) . . ?
O1 Co1 N1 91.52(10) . . ?
O2W Co1 N4 90.86(10) . 2 ?
O1 Co1 N4 95.94(10) . 2 ?
N1 Co1 N4 100.98(11) . 2 ?
O2W Co1 O1W 91.33(10) . . ?
O1 Co1 O1W 176.35(9) . . ?
N1 Co1 O1W 90.45(10) . . ?
N4 Co1 O1W 86.69(10) 2 . ?
O2W Co1 O3W 80.27(10) . . ?
O1 Co1 O3W 92.38(9) . . ?
N1 Co1 O3W 88.19(10) . . ?
N4 Co1 O3W 167.41(10) 2 . ?
O1W Co1 O3W 84.61(10) . . ?
O1 C1 C2 135.5(3) . . ?
O1 C1 C4 134.8(3) . . ?
C2 C1 C4 89.7(3) . . ?
N5 C2 C1 139.4(3) . . ?
N5 C2 C3 127.5(3) . . ?
C1 C2 C3 93.1(3) . . ?
O3 C3 C2 134.0(3) . . ?
O3 C3 C4 137.3(3) . . ?
C2 C3 C4 88.6(3) . . ?
O4 C4 C1 135.3(3) . . ?
O4 C4 C3 136.2(3) . . ?
C1 C4 C3 88.5(3) . . ?
N1 C5 N4 111.7(3) . . ?
N1 C5 N5 126.4(3) . . ?
N4 C5 N5 121.9(3) . . ?
C5 N1 N2 104.8(3) . . ?
C5 N1 Co1 135.9(2) . . ?
N2 N1 Co1 117.6(2) . . ?
N3 N2 N1 109.7(3) . . ?
N2 N3 N4 109.4(3) . . ?
C5 N4 N3 104.3(3) . . ?
C5 N4 Co1 133.1(2) . 2_545 ?
N3 N4 Co1 119.6(2) . 2_545 ?
C1 O1 Co1 118.1(2) . . ?
C2 N5 C5 126.2(3) . . ?
C2 N5 H5 119(3) . . ?
C5 N5 H5 114(3) . . ?
Co1 O1W H11W 122(3) . . ?
Co1 O1W H12W 125(3) . . ?
H11W O1W H12W 106(4) . . ?
Co1 O2W H21W 122(3) . . ?
Co1 O2W H22W 109(3) . . ?
H21W O2W H22W 108(4) . . ?
Co1 O3W H31W 105(2) . . ?
Co1 O3W H32W 104(3) . . ?
H31W O3W H32W 103(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
O1W H11W N3 0.86(2) 2.09(3) 2.889(4) 155(4) 3_556
O1W H12W O1 0.86(2) 1.98(2) 2.799(3) 159(4) 4_566
O2W H21W N3 0.87(2) 2.62(5) 3.039(4) 110(4) 2
O2W H21W O3W 0.87(2) 2.08(3) 2.830(3) 144(4) 2_655
O3W H31W O3 0.87(2) 1.81(2) 2.670(3) 172(4) 4_556
N5 H5 N2 0.838(19) 1.96(2) 2.802(4) 179(4) 2_545
O2W H22W O4 0.88(2) 1.90(3) 2.737(3) 159(5) 3_655
O3W H32W O3 0.86(2) 2.08(2) 2.926(3) 167(4) 2_655
O1W H11W N3 0.86(2) 2.09(3) 2.889(4) 155(4) 3_556
O1W H12W O1 0.86(2) 1.98(2) 2.799(3) 159(4) 4_566
O2W H21W N3 0.87(2) 2.62(5) 3.039(4) 110(4) 2
O2W H21W O3W 0.87(2) 2.08(3) 2.830(3) 144(4) 2_655
O3W H31W O3 0.87(2) 1.81(2) 2.670(3) 172(4) 4_556
N5 H5 N2 0.838(19) 1.96(2) 2.802(4) 179(4) 2_545
O2W H22W O4 0.88(2) 1.90(3) 2.737(3) 159(5) 3_655
O3W H32W O3 0.86(2) 2.08(2) 2.926(3) 167(4) 2_655

_refine_diff_density_max         0.797
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.129

_shelxl_version_number           2014-3

