# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_S-2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H11 Co N Na O6'
_chemical_formula_weight         287.09
_chemical_absolute_configuration S

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'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   8.3415(3)
_cell_length_b                   9.3745(4)
_cell_length_c                   13.5440(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1059.11(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3250
_cell_measurement_theta_min      3.5979
_cell_measurement_theta_max      27.4547

_exptl_crystal_description       Prism
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.6000
_exptl_crystal_size_mid          0.4000
_exptl_crystal_size_min          0.4000
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.800
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    1.672
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8402
_exptl_absorpt_correction_T_max  1.0000
_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            6640
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.60
_diffrn_reflns_theta_max         24.96
_reflns_number_total             1818
_reflns_number_gt                1761
_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)+(0.0605P)²+0.2791P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_number_reflns         1818
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0280
_refine_ls_wR_factor_ref         0.0844
_refine_ls_wR_factor_gt          0.0837
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.92465(5) 0.41649(5) 0.17215(3) 0.01697(15) Uani 1 1 d . . .
O6 O 0.8283(3) 0.3233(3) 0.30531(17) 0.0316(6) Uani 1 1 d . . .
H6A H 0.8677 0.2441 0.3137 0.047 Uiso 1 1 calc R . .
O5 O 0.9397(3) 0.6072(3) -0.09576(17) 0.0312(6) Uani 1 1 d . . .
O4 O 0.8625(3) 0.8142(3) 0.29175(17) 0.0217(5) Uani 1 1 d . . .
O3 O 0.7943(3) 0.2622(3) 0.09398(17) 0.0263(6) Uani 1 1 d . . .
C2 C 0.9178(4) 0.5712(4) -0.0074(2) 0.0196(6) Uani 1 1 d . . .
O2 O 0.9677(3) 0.6026(3) 0.25276(18) 0.0266(6) Uani 1 1 d . . .
O1 O 1.0117(3) 0.4947(3) 0.04129(18) 0.0271(6) Uani 1 1 d . . .
N1 N 0.7205(3) 0.5461(3) 0.13067(18) 0.0158(6) Uani 1 1 d . . .
C4 C 0.6533(5) 0.3219(4) 0.0491(3) 0.0303(9) Uani 1 1 d . . .
H4A H 0.5725 0.2482 0.0421 0.036 Uiso 1 1 calc R . .
H4B H 0.6797 0.3569 -0.0163 0.036 Uiso 1 1 calc R . .
C3 C 0.5861(4) 0.4440(4) 0.1111(2) 0.0216(7) Uani 1 1 d . . .
H3A H 0.5549 0.4033 0.1749 0.026 Uiso 1 1 calc R . .
C1 C 0.7683(4) 0.6296(4) 0.0436(2) 0.0233(8) Uani 1 1 d . . .
H1A H 0.7883 0.7273 0.0637 0.028 Uiso 1 1 calc R . .
H1B H 0.6804 0.6305 -0.0032 0.028 Uiso 1 1 calc R . .
C6 C 0.6922(4) 0.6408(4) 0.2162(2) 0.0192(7) Uani 1 1 d . . .
H6B H 0.6325 0.5901 0.2667 0.023 Uiso 1 1 calc R . .
H6C H 0.6298 0.7230 0.1958 0.023 Uiso 1 1 calc R . .
C5 C 0.4370(5) 0.5067(4) 0.0658(3) 0.0354(9) Uani 1 1 d . . .
H5A H 0.3983 0.5830 0.1066 0.053 Uiso 1 1 calc R . .
H5B H 0.3561 0.4342 0.0606 0.053 Uiso 1 1 calc R . .
H5C H 0.4615 0.5429 0.0012 0.053 Uiso 1 1 calc R . .
C9 C 0.8527(4) 0.6892(4) 0.2573(2) 0.0184(7) Uani 1 1 d . . .
Na1 Na 0.6896(4) 0.0320(3) 0.1823(3) 0.1022(9) 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
Co1 0.0184(2) 0.0139(3) 0.0186(2) 0.00120(18) -0.00197(16) 0.00147(18)
O6 0.0378(15) 0.0268(15) 0.0301(13) 0.0054(12) 0.0123(11) 0.0068(12)
O5 0.0292(12) 0.0409(16) 0.0234(12) 0.0103(12) 0.0050(10) 0.0116(13)
O4 0.0192(11) 0.0185(14) 0.0276(12) -0.0069(10) -0.0041(9) -0.0030(10)
O3 0.0287(13) 0.0184(14) 0.0319(12) -0.0051(12) -0.0057(11) 0.0016(11)
C2 0.0199(14) 0.0161(17) 0.0227(15) 0.0014(13) 0.0006(13) -0.0015(16)
O2 0.0234(12) 0.0180(14) 0.0382(13) -0.0069(12) -0.0116(10) 0.0026(10)
O1 0.0201(12) 0.0323(17) 0.0289(13) 0.0106(11) 0.0028(10) 0.0069(11)
N1 0.0156(12) 0.0155(16) 0.0163(12) 0.0000(11) -0.0002(10) 0.0003(11)
C4 0.034(2) 0.025(2) 0.0315(18) -0.0099(16) -0.0099(16) 0.0004(18)
C3 0.0209(15) 0.0197(18) 0.0241(15) -0.0028(14) -0.0041(13) -0.0041(15)
C1 0.0257(18) 0.021(2) 0.0232(17) 0.0060(14) 0.0014(14) 0.0060(14)
C6 0.0184(16) 0.0166(18) 0.0225(15) -0.0026(14) 0.0023(13) -0.0001(13)
C5 0.0235(19) 0.032(2) 0.050(2) -0.0118(18) -0.0133(18) 0.0053(17)
C9 0.0191(16) 0.0164(18) 0.0196(15) -0.0004(14) -0.0022(12) -0.0034(15)
Na1 0.0897(19) 0.085(2) 0.132(2) 0.019(2) -0.0297(19) -0.0105(15)

_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 O1 2.051(2) . ?
Co1 O4 2.076(2) 3_745 ?
Co1 O2 2.089(2) . ?
Co1 O3 2.096(2) . ?
Co1 O6 2.159(2) . ?
Co1 N1 2.166(3) . ?
O5 C2 1.257(4) . ?
O5 Na1 2.724(4) 4 ?
O4 C9 1.264(4) . ?
O4 Co1 2.076(2) 3_755 ?
O4 Na1 2.906(4) 1_565 ?
O3 C4 1.437(4) . ?
O3 Na1 2.618(4) . ?
C2 O1 1.249(4) . ?
C2 C1 1.527(5) . ?
O2 C9 1.258(4) . ?
N1 C1 1.470(4) . ?
N1 C6 1.478(4) . ?
N1 C3 1.499(4) . ?
C4 C3 1.526(5) . ?
C3 C5 1.507(5) . ?
C6 C9 1.519(4) . ?
Na1 O5 2.724(4) 4_455 ?
Na1 O4 2.906(4) 1_545 ?

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
O1 Co1 O4 93.78(9) . 3_745 ?
O1 Co1 O2 95.28(10) . . ?
O4 Co1 O2 96.65(9) 3_745 . ?
O1 Co1 O3 89.65(10) . . ?
O4 Co1 O3 104.12(9) 3_745 . ?
O2 Co1 O3 158.30(9) . . ?
O1 Co1 O6 176.66(11) . . ?
O4 Co1 O6 86.26(10) 3_745 . ?
O2 Co1 O6 88.03(10) . . ?
O3 Co1 O6 87.10(10) . . ?
O1 Co1 N1 81.57(9) . . ?
O4 Co1 N1 172.93(10) 3_745 . ?
O2 Co1 N1 78.58(9) . . ?
O3 Co1 N1 81.28(10) . . ?
O6 Co1 N1 98.69(10) . . ?
C2 O5 Na1 113.1(2) . 4 ?
C9 O4 Co1 124.8(2) . 3_755 ?
C9 O4 Na1 115.5(2) . 1_565 ?
Co1 O4 Na1 102.72(11) 3_755 1_565 ?
C4 O3 Co1 111.7(2) . . ?
C4 O3 Na1 104.0(2) . . ?
Co1 O3 Na1 120.74(12) . . ?
O1 C2 O5 124.4(3) . . ?
O1 C2 C1 118.6(3) . . ?
O5 C2 C1 116.9(3) . . ?
C9 O2 Co1 115.7(2) . . ?
C2 O1 Co1 116.0(2) . . ?
C1 N1 C6 110.6(3) . . ?
C1 N1 C3 113.7(3) . . ?
C6 N1 C3 113.7(2) . . ?
C1 N1 Co1 107.1(2) . . ?
C6 N1 Co1 105.04(19) . . ?
C3 N1 Co1 106.0(2) . . ?
O3 C4 C3 111.1(3) . . ?
N1 C3 C4 107.5(3) . . ?
N1 C3 C5 116.1(3) . . ?
C4 C3 C5 111.8(3) . . ?
N1 C1 C2 113.2(3) . . ?
N1 C6 C9 109.0(3) . . ?
O2 C9 O4 124.5(3) . . ?
O2 C9 C6 117.5(3) . . ?
O4 C9 C6 118.0(3) . . ?
O3 Na1 O5 116.98(13) . 4_455 ?
O3 Na1 O4 130.28(13) . 1_545 ?
O5 Na1 O4 105.24(12) 4_455 1_545 ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        24.96
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.566
_refine_diff_density_rms         0.073
_database_code_depnum_ccdc_archive 'CCDC 1020719'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_S-1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H14 Co N Na O7'
_chemical_formula_weight         306.11
_chemical_absolute_configuration S

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'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   7.0082(5)
_cell_length_b                   12.1505(7)
_cell_length_c                   13.9281(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1186.02(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3752
_cell_measurement_theta_min      2.9066
_cell_measurement_theta_max      27.4856

_exptl_crystal_description       Prism
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.6000
_exptl_crystal_size_mid          0.4000
_exptl_crystal_size_min          0.3000
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             628
_exptl_absorpt_coefficient_mu    1.505
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8453
_exptl_absorpt_correction_T_max  1.0000
_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            7115
_diffrn_reflns_av_R_equivalents  0.0147
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2084
_reflns_number_gt                2041
_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)+(0.0543P)²+0.7524P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_number_reflns         2084
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0853
_refine_ls_wR_factor_gt          0.0849
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.34229(6) 1.13475(3) 0.64216(3) 0.01905(14) Uani 1 1 d . . .
Na1 Na -0.1460(4) 1.1549(2) 0.79618(19) 0.0897(8) Uani 1 1 d . . .
C1 C 0.3147(5) 0.8933(3) 0.6512(2) 0.0263(7) Uani 1 1 d . . .
H1A H 0.4069 0.8736 0.7002 0.032 Uiso 1 1 calc R . .
H1B H 0.2815 0.8269 0.6163 0.032 Uiso 1 1 calc R . .
C2 C 0.1379(5) 0.9389(3) 0.6989(2) 0.0282(8) Uani 1 1 d . . .
C3 C 0.3175(6) 0.9667(3) 0.4871(2) 0.0280(8) Uani 1 1 d . . .
H3A H 0.2410 0.9004 0.4830 0.034 Uiso 1 1 calc R . .
H3B H 0.4194 0.9605 0.4403 0.034 Uiso 1 1 calc R . .
C4 C 0.1926(5) 1.0652(3) 0.4604(2) 0.0222(7) Uani 1 1 d . . .
C5 C 0.6167(5) 0.9664(3) 0.5858(2) 0.0253(7) Uani 1 1 d . . .
H5A H 0.6560 0.9685 0.6533 0.030 Uiso 1 1 calc R . .
C6 C 0.6971(5) 1.0679(3) 0.5382(3) 0.0361(9) Uani 1 1 d . . .
H6A H 0.8346 1.0698 0.5462 0.043 Uiso 1 1 calc R . .
H6B H 0.6692 1.0664 0.4700 0.043 Uiso 1 1 calc R . .
C7 C 0.6978(5) 0.8606(3) 0.5426(3) 0.0363(9) Uani 1 1 d . . .
H7A H 0.6431 0.7982 0.5747 0.054 Uiso 1 1 calc R . .
H7B H 0.8338 0.8597 0.5506 0.054 Uiso 1 1 calc R . .
H7C H 0.6672 0.8575 0.4755 0.054 Uiso 1 1 calc R . .
O1 O 0.1171(3) 1.0430(2) 0.69918(18) 0.0319(6) Uani 1 1 d . . .
O2 O 0.0253(4) 0.8737(2) 0.7367(2) 0.0470(8) Uani 1 1 d . . .
O3 O 0.0889(4) 1.0562(2) 0.38842(17) 0.0316(6) Uani 1 1 d . . .
O4 O 0.2043(4) 1.15078(19) 0.51160(17) 0.0302(6) Uani 1 1 d . . .
O5 O 0.6137(4) 1.1635(2) 0.58090(19) 0.0318(6) Uani 1 1 d . . .
O6 O 0.2969(4) 1.30148(19) 0.66983(18) 0.0308(6) Uani 1 1 d . . .
H6C H 0.3113 1.3513 0.6226 0.037 Uiso 1 1 d R . .
H6D H 0.2627 1.3235 0.7291 0.037 Uiso 1 1 d R . .
O7 O 0.4765(4) 1.1203(2) 0.77354(16) 0.0331(6) Uani 1 1 d . . .
H7D H 0.5362 1.0572 0.7891 0.040 Uiso 1 1 d R . .
H7E H 0.4755 1.1769 0.8152 0.040 Uiso 1 1 d R . .
N1 N 0.4027(4) 0.9732(2) 0.58408(19) 0.0186(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
Co1 0.0214(2) 0.0153(2) 0.0204(2) 0.00097(17) 0.00140(17) 0.00017(17)
Na1 0.0799(16) 0.096(2) 0.0934(18) -0.0134(14) 0.0099(14) 0.0094(16)
C1 0.0303(17) 0.0163(15) 0.0322(17) 0.0034(13) 0.0062(16) 0.0005(13)
C2 0.0248(17) 0.0241(18) 0.0355(18) 0.0016(14) 0.0025(16) -0.0041(15)
C3 0.034(2) 0.0213(17) 0.0287(17) -0.0046(13) -0.0101(16) 0.0110(16)
C4 0.0242(17) 0.0209(17) 0.0214(15) 0.0003(13) 0.0002(14) 0.0008(13)
C5 0.0196(16) 0.0280(18) 0.0282(17) 0.0027(14) 0.0007(14) 0.0042(14)
C6 0.0277(19) 0.034(2) 0.046(2) 0.0031(17) 0.0163(17) 0.0011(15)
C7 0.034(2) 0.033(2) 0.041(2) 0.0003(17) 0.0056(16) 0.0177(18)
O1 0.0272(14) 0.0224(13) 0.0462(15) 0.0009(11) 0.0141(12) 0.0034(11)
O2 0.0349(14) 0.0300(15) 0.076(2) 0.0144(15) 0.0242(14) -0.0048(13)
O3 0.0332(13) 0.0314(14) 0.0302(13) -0.0035(11) -0.0119(11) 0.0101(11)
O4 0.0417(14) 0.0186(12) 0.0304(12) -0.0015(10) -0.0124(10) 0.0060(11)
O5 0.0316(13) 0.0243(13) 0.0394(14) 0.0040(10) 0.0123(11) -0.0015(10)
O6 0.0392(15) 0.0173(12) 0.0359(13) -0.0028(10) 0.0116(11) -0.0011(10)
O7 0.0389(14) 0.0336(15) 0.0267(13) 0.0072(12) -0.0043(11) -0.0044(12)
N1 0.0184(12) 0.0171(13) 0.0202(13) 0.0016(10) 0.0025(11) 0.0028(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
Co1 O4 2.069(2) . ?
Co1 O7 2.065(2) . ?
Co1 O1 2.089(2) . ?
Co1 O6 2.087(2) . ?
Co1 O5 2.114(2) . ?
Co1 N1 2.165(3) . ?
Na1 O1 2.659(3) . ?
Na1 O7 2.697(4) 1_455 ?
Na1 O2 2.828(4) 3_556 ?
C1 N1 1.482(4) . ?
C1 C2 1.511(5) . ?
C2 O2 1.236(4) . ?
C2 O1 1.274(5) . ?
C3 N1 1.479(4) . ?
C3 C4 1.528(4) . ?
C4 O3 1.243(4) . ?
C4 O4 1.264(4) . ?
C5 N1 1.502(4) . ?
C5 C6 1.509(5) . ?
C5 C7 1.529(5) . ?
C6 O5 1.430(5) . ?
O2 Na1 2.828(4) 3_546 ?
O7 Na1 2.697(4) 1_655 ?

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
O4 Co1 O7 179.04(11) . . ?
O4 Co1 O1 91.79(11) . . ?
O7 Co1 O1 87.81(10) . . ?
O4 Co1 O6 89.98(10) . . ?
O7 Co1 O6 89.33(11) . . ?
O1 Co1 O6 109.42(10) . . ?
O4 Co1 O5 92.88(11) . . ?
O7 Co1 O5 87.81(10) . . ?
O1 Co1 O5 157.16(10) . . ?
O6 Co1 O5 92.93(10) . . ?
O4 Co1 N1 81.29(9) . . ?
O7 Co1 N1 99.49(11) . . ?
O1 Co1 N1 78.82(10) . . ?
O6 Co1 N1 168.29(10) . . ?
O5 Co1 N1 79.83(10) . . ?
O1 Na1 O7 122.76(13) . 1_455 ?
O1 Na1 O2 101.00(12) . 3_556 ?
O7 Na1 O2 114.90(14) 1_455 3_556 ?
N1 C1 C2 112.3(3) . . ?
O2 C2 O1 124.2(3) . . ?
O2 C2 C1 118.5(3) . . ?
O1 C2 C1 117.3(3) . . ?
N1 C3 C4 114.3(3) . . ?
O3 C4 O4 124.4(3) . . ?
O3 C4 C3 117.5(3) . . ?
O4 C4 C3 118.0(3) . . ?
N1 C5 C6 108.8(3) . . ?
N1 C5 C7 114.2(3) . . ?
C6 C5 C7 112.1(3) . . ?
O5 C6 C5 109.2(3) . . ?
C2 O1 Co1 116.2(2) . . ?
C2 O1 Na1 126.1(2) . . ?
Co1 O1 Na1 116.38(13) . . ?
C2 O2 Na1 110.0(2) . 3_546 ?
C4 O4 Co1 116.7(2) . . ?
C6 O5 Co1 113.6(2) . . ?
Co1 O7 Na1 122.49(12) . 1_655 ?
C3 N1 C1 111.9(3) . . ?
C3 N1 C5 114.5(3) . . ?
C1 N1 C5 111.7(3) . . ?
C3 N1 Co1 108.06(19) . . ?
C1 N1 Co1 106.05(19) . . ?
C5 N1 Co1 103.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.551
_refine_diff_density_rms         0.074
_database_code_depnum_ccdc_archive 'CCDC 1020718'
