# 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

#######################################################################
#
#                 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_epr251-r

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H27 Co N2 O9'
_chemical_formula_weight         522.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   15.959(5)
_cell_length_b                   11.194(3)
_cell_length_c                   13.281(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.678(5)
_cell_angle_gamma                90.00
_cell_volume                     2331.4(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088
_exptl_absorpt_coefficient_mu    0.791
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.7638
_exptl_absorpt_correction_T_max  0.9322
_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            23447
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.30
_diffrn_reflns_theta_max         25.97
_reflns_number_total             4563
_reflns_number_gt                3741
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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 > 2σ(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)+(0.0820P)²+1.4732P] 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         4563
_refine_ls_number_parameters     318
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.1542
_refine_ls_wR_factor_gt          0.1456
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4006(3) -0.1238(3) 0.9629(4) 0.0761(12) Uani 1 1 d . . .
C2 C 0.4434(4) -0.2007(4) 0.9079(5) 0.1057(19) Uani 1 1 d . . .
H2 H 0.4951 -0.2340 0.9392 0.127 Uiso 1 1 calc R . .
C3 C 0.4096(5) -0.2284(5) 0.8063(6) 0.127(3) Uani 1 1 d . . .
H3 H 0.4383 -0.2820 0.7714 0.153 Uiso 1 1 calc R . .
C4 C 0.3361(5) -0.1792(4) 0.7574(4) 0.110(2) Uani 1 1 d . . .
H4 H 0.3160 -0.1965 0.6886 0.132 Uiso 1 1 calc R . .
C5 C 0.2895(4) -0.1011(3) 0.8106(3) 0.0791(13) Uani 1 1 d . . .
C6 C 0.3210(3) -0.0728(3) 0.9144(3) 0.0690(11) Uani 1 1 d . . .
C7 C 0.2117(4) -0.0557(4) 0.7577(3) 0.0843(15) Uani 1 1 d . . .
H7 H 0.1946 -0.0799 0.6900 0.101 Uiso 1 1 calc R . .
C8 C 0.0783(3) 0.0529(5) 0.7361(3) 0.0995(17) Uani 1 1 d . . .
H8A H 0.0349 -0.0043 0.7462 0.119 Uiso 1 1 calc R . .
H8B H 0.0799 0.0567 0.6635 0.119 Uiso 1 1 calc R . .
C9 C 0.0584(3) 0.1731(5) 0.7744(3) 0.0906(14) Uani 1 1 d . . .
H9A H 0.0942 0.2337 0.7518 0.109 Uiso 1 1 calc R . .
H9B H -0.0009 0.1936 0.7492 0.109 Uiso 1 1 calc R . .
C10 C 0.5106(3) -0.1308(5) 1.1084(4) 0.0990(17) Uani 1 1 d . . .
H10A H 0.5083 -0.2153 1.1199 0.149 Uiso 1 1 calc R . .
H10B H 0.5274 -0.0906 1.1728 0.149 Uiso 1 1 calc R . .
H10C H 0.5514 -0.1145 1.0653 0.149 Uiso 1 1 calc R . .
C11 C 0.34039(19) 0.3639(3) 0.8993(2) 0.0494(7) Uani 1 1 d . . .
C12 C 0.3886(2) 0.4491(3) 0.9584(3) 0.0604(9) Uani 1 1 d . . .
H12 H 0.4232 0.4996 0.9284 0.072 Uiso 1 1 calc R . .
C13 C 0.3865(2) 0.4612(4) 1.0618(3) 0.0672(10) Uani 1 1 d . . .
H13 H 0.4194 0.5193 1.1005 0.081 Uiso 1 1 calc R . .
C14 C 0.3364(2) 0.3885(3) 1.1061(3) 0.0589(9) Uani 1 1 d . . .
H14 H 0.3352 0.3970 1.1755 0.071 Uiso 1 1 calc R . .
C15 C 0.28613(19) 0.3001(3) 1.0489(2) 0.0469(7) Uani 1 1 d . . .
C16 C 0.28723(18) 0.2853(3) 0.9434(2) 0.0441(6) Uani 1 1 d . . .
C17 C 0.23264(19) 0.2293(3) 1.1012(2) 0.0480(7) Uani 1 1 d . . .
H17 H 0.2299 0.2499 1.1683 0.058 Uiso 1 1 calc R . .
C18 C 0.1340(3) 0.0735(3) 1.1204(3) 0.0669(10) Uani 1 1 d . . .
H18A H 0.0767 0.1061 1.1075 0.080 Uiso 1 1 calc R . .
H18B H 0.1567 0.0786 1.1932 0.080 Uiso 1 1 calc R . .
C19 C 0.1331(3) -0.0529(4) 1.0853(3) 0.0763(11) Uani 1 1 d . . .
H19A H 0.1879 -0.0905 1.1095 0.092 Uiso 1 1 calc R . .
H19B H 0.0894 -0.0980 1.1107 0.092 Uiso 1 1 calc R . .
C20 C 0.3825(3) 0.4312(4) 0.7457(3) 0.0814(13) Uani 1 1 d . . .
H20A H 0.3611 0.5103 0.7530 0.122 Uiso 1 1 calc R . .
H20B H 0.3744 0.4109 0.6743 0.122 Uiso 1 1 calc R . .
H20C H 0.4421 0.4284 0.7750 0.122 Uiso 1 1 calc R . .
C21 C 0.1309(3) 0.6553(4) 0.9296(4) 0.0811(12) Uani 1 1 d . . .
C22 C 0.1999(6) 0.6086(9) 0.8898(8) 0.230(6) Uani 1 1 d . . .
H22A H 0.1870 0.6116 0.8163 0.345 Uiso 1 1 calc R . .
H22B H 0.2096 0.5272 0.9117 0.345 Uiso 1 1 calc R . .
H22C H 0.2501 0.6550 0.9143 0.345 Uiso 1 1 calc R . .
Co1 Co 0.18183(3) 0.07997(4) 0.92811(3) 0.04953(18) Uani 1 1 d . . .
N1 N 0.1615(2) 0.0163(3) 0.7939(2) 0.0705(9) Uani 1 1 d . . .
N2 N 0.18856(16) 0.1401(2) 1.06211(18) 0.0477(6) Uani 1 1 d . . .
O1 O 0.28226(16) -0.0041(2) 0.97149(18) 0.0616(6) Uani 1 1 d . . .
O2 O 0.07496(15) 0.1648(2) 0.88432(18) 0.0664(7) Uani 1 1 d . . .
O3 O 0.24123(14) 0.20747(19) 0.88249(15) 0.0503(5) Uani 1 1 d . . .
O4 O 0.11490(18) -0.0475(2) 0.97488(19) 0.0703(7) Uani 1 1 d . . .
O5 O 0.4290(2) -0.0896(3) 1.0598(3) 0.0840(9) Uani 1 1 d . . .
O6 O 0.33749(16) 0.3480(2) 0.79733(17) 0.0616(6) Uani 1 1 d . . .
O7 O 0.1013(3) 0.7535(3) 0.9049(4) 0.1463(19) Uani 1 1 d . . .
O8 O 0.0988(3) 0.5924(5) 0.9890(4) 0.1485(19) Uani 1 1 d . . .
O9 O 0.0535(3) 0.3586(4) 0.9678(4) 0.1166(13) Uani 1 1 d D . .
H9X H 0.0029(16) 0.360(4) 0.981(3) 0.078(14) Uiso 1 1 d D . .
H9Y H 0.073(9) 0.379(13) 0.914(7) 0.36(8) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O5 1.339(6) . ?
C1 C2 1.387(6) . ?
C1 C6 1.431(6) . ?
C2 C3 1.392(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.348(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.419(6) . ?
C4 H4 0.9300 . ?
C5 C7 1.405(7) . ?
C5 C6 1.413(6) . ?
C6 O1 1.313(4) . ?
C7 N1 1.290(6) . ?
C7 H7 0.9300 . ?
C8 N1 1.464(6) . ?
C8 C9 1.494(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O2 1.438(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 O5 1.419(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 O6 1.358(4) . ?
C11 C12 1.377(5) . ?
C11 C16 1.422(4) . ?
C12 C13 1.386(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.349(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.405(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.414(4) . ?
C15 C17 1.435(4) . ?
C16 O3 1.316(3) . ?
C17 N2 1.275(4) . ?
C17 H17 0.9300 . ?
C18 N2 1.470(4) . ?
C18 C19 1.489(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 O4 1.443(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 O6 1.426(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 O7 1.218(5) . ?
C21 O8 1.236(6) . ?
C21 C22 1.408(9) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
Co1 O1 1.856(2) . ?
Co1 O3 1.875(2) . ?
Co1 N2 1.887(3) . ?
Co1 N1 1.891(3) . ?
Co1 O2 1.945(3) . ?
Co1 O4 1.952(3) . ?
O9 H9X 0.860(19) . ?
O9 H9Y 0.85(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
O5 C1 C2 124.8(5) . . ?
O5 C1 C6 115.6(3) . . ?
C2 C1 C6 119.5(5) . . ?
C1 C2 C3 120.5(6) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 121.5(5) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 120.0(5) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C7 C5 C6 122.0(4) . . ?
C7 C5 C4 118.0(5) . . ?
C6 C5 C4 120.0(5) . . ?
O1 C6 C5 125.0(4) . . ?
O1 C6 C1 116.6(4) . . ?
C5 C6 C1 118.4(4) . . ?
N1 C7 C5 126.3(4) . . ?
N1 C7 H7 116.9 . . ?
C5 C7 H7 116.9 . . ?
N1 C8 C9 107.6(3) . . ?
N1 C8 H8A 110.2 . . ?
C9 C8 H8A 110.2 . . ?
N1 C8 H8B 110.2 . . ?
C9 C8 H8B 110.2 . . ?
H8A C8 H8B 108.5 . . ?
O2 C9 C8 106.1(4) . . ?
O2 C9 H9A 110.5 . . ?
C8 C9 H9A 110.5 . . ?
O2 C9 H9B 110.5 . . ?
C8 C9 H9B 110.5 . . ?
H9A C9 H9B 108.7 . . ?
O5 C10 H10A 109.5 . . ?
O5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O6 C11 C12 124.9(3) . . ?
O6 C11 C16 114.7(3) . . ?
C12 C11 C16 120.4(3) . . ?
C11 C12 C13 121.3(3) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C12 119.9(3) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.9(3) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C14 C15 C16 120.5(3) . . ?
C14 C15 C17 117.3(3) . . ?
C16 C15 C17 122.2(3) . . ?
O3 C16 C15 125.3(3) . . ?
O3 C16 C11 117.6(3) . . ?
C15 C16 C11 117.0(3) . . ?
N2 C17 C15 124.6(3) . . ?
N2 C17 H17 117.7 . . ?
C15 C17 H17 117.7 . . ?
N2 C18 C19 106.9(3) . . ?
N2 C18 H18A 110.3 . . ?
C19 C18 H18A 110.3 . . ?
N2 C18 H18B 110.3 . . ?
C19 C18 H18B 110.3 . . ?
H18A C18 H18B 108.6 . . ?
O4 C19 C18 105.5(3) . . ?
O4 C19 H19A 110.6 . . ?
C18 C19 H19A 110.6 . . ?
O4 C19 H19B 110.6 . . ?
C18 C19 H19B 110.6 . . ?
H19A C19 H19B 108.8 . . ?
O6 C20 H20A 109.5 . . ?
O6 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O6 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O7 C21 O8 120.0(6) . . ?
O7 C21 C22 121.7(6) . . ?
O8 C21 C22 118.2(5) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O1 Co1 O3 91.56(11) . . ?
O1 Co1 N2 89.62(10) . . ?
O3 Co1 N2 95.12(10) . . ?
O1 Co1 N1 95.11(14) . . ?
O3 Co1 N1 89.47(11) . . ?
N2 Co1 N1 173.33(13) . . ?
O1 Co1 O2 178.46(11) . . ?
O3 Co1 O2 89.97(10) . . ?
N2 Co1 O2 90.07(11) . . ?
N1 Co1 O2 85.08(14) . . ?
O1 Co1 O4 91.28(12) . . ?
O3 Co1 O4 177.08(11) . . ?
N2 Co1 O4 84.25(11) . . ?
N1 Co1 O4 90.93(12) . . ?
O2 Co1 O4 87.18(12) . . ?
C7 N1 C8 123.0(4) . . ?
C7 N1 Co1 125.2(3) . . ?
C8 N1 Co1 111.7(3) . . ?
C17 N2 C18 121.2(3) . . ?
C17 N2 Co1 126.4(2) . . ?
C18 N2 Co1 112.3(2) . . ?
C6 O1 Co1 126.2(3) . . ?
C9 O2 Co1 108.8(3) . . ?
C16 O3 Co1 124.27(19) . . ?
C19 O4 Co1 109.6(2) . . ?
C1 O5 C10 117.6(4) . . ?
C11 O6 C20 117.8(3) . . ?
H9X O9 H9Y 132(10) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.97
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.575
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.068
_database_code_depnum_ccdc_archive 'CCDC 918017'
