# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2013

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#                                CCDC 
# 
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# 
#  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.
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#  fide research purposes only. It may contain copyright material
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data_SKComplex1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H30 Co3 N2 O14'
_chemical_formula_sum            'C28 H30 Co3 N2 O14'
_chemical_formula_weight         795.33

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           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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

_cell_length_a                   11.6092(7)
_cell_length_b                   9.0436(5)
_cell_length_c                   14.3380(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.713(3)
_cell_angle_gamma                90.00
_cell_volume                     1449.08(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7383
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      29.61

_exptl_crystal_description       Block
_exptl_crystal_colour            Pink
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.823
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             810.0
_exptl_absorpt_coefficient_mu    1.776
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.479
_exptl_absorpt_correction_T_max  0.608
_exptl_absorpt_process_details   Empirical

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            4599
_diffrn_reflns_av_R_equivalents  0.0106
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.20
_diffrn_reflns_theta_max         29.49
_reflns_number_total             4041
_reflns_number_gt                3091
_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 F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ 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/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4041
_refine_ls_number_parameters     215
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.1113
_refine_ls_wR_factor_gt          0.1090
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_restrained_S_all      0.951
_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 0.78068(2) 1.09122(3) 0.072270(19) 0.01543(12) Uani 1 1 d . . .
Co2 Co 1.0000 1.0000 0.0000 0.01219(12) Uani 1 2 d S . .
N1 N 0.64702(17) 1.24582(19) 0.00257(14) 0.0225(4) Uani 1 1 d . . .
C1 C 0.5304(2) 1.2175(2) -0.01154(19) 0.0281(5) Uani 1 1 d . . .
H1 H 0.5080 1.1381 0.0209 0.034 Uiso 1 1 calc R . .
C2 C 0.4420(3) 1.3019(3) -0.0725(2) 0.0436(7) Uani 1 1 d . . .
H2 H 0.3617 1.2811 -0.0795 0.052 Uiso 1 1 calc R . .
C3 C 0.4744(3) 1.4161(4) -0.1224(3) 0.0636(11) Uani 1 1 d . . .
H3 H 0.4167 1.4747 -0.1637 0.076 Uiso 1 1 calc R . .
C6 C 0.6770(3) 1.3591(3) -0.0467(2) 0.0437(7) Uani 1 1 d . . .
H6 H 0.7576 1.3813 -0.0370 0.052 Uiso 1 1 calc R . .
O1 O 0.84455(14) 0.80081(15) 0.21397(11) 0.0235(4) Uani 1 1 d . . .
O2 O 0.92108(13) 0.93468(14) 0.11526(10) 0.0156(3) Uani 1 1 d . . .
C8 C 1.01918(18) 0.70356(19) 0.17637(15) 0.0161(4) Uani 1 1 d . . .
H8 H 1.0744 0.7371 0.1398 0.019 Uiso 1 1 calc R . .
C11 C 1.1160(2) 0.40991(18) 0.25178(16) 0.0187(4) Uani 1 1 d . . .
H11A H 1.1750 0.3320 0.2581 0.022 Uiso 1 1 calc R . .
H11B H 1.0587 0.3791 0.2862 0.022 Uiso 1 1 calc R . .
C13 C 1.0889(2) 0.6813(2) 0.28258(16) 0.0209(4) Uani 1 1 d . . .
H13A H 1.1315 0.7719 0.3066 0.025 Uiso 1 1 calc R . .
H13B H 1.0326 0.6626 0.3204 0.025 Uiso 1 1 calc R . .
C10 C 1.05145(18) 0.43232(19) 0.14480(14) 0.0164(4) Uani 1 1 d . . .
H10 H 1.1105 0.4574 0.1098 0.020 Uiso 1 1 calc R . .
C12 C 1.17872(17) 0.5538(2) 0.29798(14) 0.0158(4) Uani 1 1 d . . .
H12 H 1.2424 0.5788 0.2677 0.019 Uiso 1 1 calc R . .
C9 C 0.96001(19) 0.55836(19) 0.13194(14) 0.0174(4) Uani 1 1 d . . .
H9A H 0.8981 0.5312 0.1626 0.021 Uiso 1 1 calc R . .
H9B H 0.9224 0.5731 0.0634 0.021 Uiso 1 1 calc R . .
O3 O 0.68545(14) 0.93633(16) -0.03289(11) 0.0217(3) Uani 1 1 d . . .
O4 O 0.82448(13) 1.06717(14) -0.07212(11) 0.0179(3) Uani 1 1 d . . .
C14 C 0.73383(18) 0.97934(19) -0.09581(15) 0.0164(4) Uani 1 1 d . . .
O7 O 0.70286(15) 1.05379(17) 0.18177(12) 0.0246(3) Uani 1 1 d . . .
H7 H 0.7368 0.9847 0.2152 0.037 Uiso 1 1 calc R . .
C7 C 0.92099(18) 0.82036(19) 0.16833(14) 0.0151(4) Uani 1 1 d . . .
O6 O 1.04441(13) 1.20419(14) 0.05991(11) 0.0196(3) Uani 1 1 d . . .
O5 O 0.89317(14) 1.25869(15) 0.12288(12) 0.0239(3) Uani 1 1 d . . .
C15 C 0.99134(18) 1.28678(19) 0.10543(14) 0.0168(4) Uani 1 1 d . . .
C5 C 0.5942(4) 1.4425(4) -0.1102(3) 0.0656(11) Uani 1 1 d . . .
H5 H 0.6185 1.5171 -0.1452 0.079 Uiso 1 1 calc R . .

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 0.0120(2) 0.01663(16) 0.0177(2) -0.00072(8) 0.00410(16) -0.00092(8)
Co2 0.0086(2) 0.01277(18) 0.0146(2) -0.00148(11) 0.00217(19) -0.00048(10)
N1 0.0166(10) 0.0232(8) 0.0266(10) 0.0041(6) 0.0042(9) 0.0015(6)
C1 0.0227(13) 0.0272(10) 0.0359(14) 0.0055(8) 0.0104(12) 0.0029(8)
C2 0.0209(16) 0.0460(15) 0.058(2) 0.0089(13) -0.0004(16) 0.0039(10)
C3 0.042(2) 0.055(2) 0.082(3) 0.0317(17) -0.004(2) 0.0135(14)
C6 0.0374(17) 0.0318(12) 0.063(2) 0.0186(12) 0.0155(16) 0.0015(10)
O1 0.0227(9) 0.0243(7) 0.0269(9) 0.0082(6) 0.0124(8) 0.0059(6)
O2 0.0143(8) 0.0154(6) 0.0172(7) 0.0020(5) 0.0045(6) 0.0020(5)
C8 0.0159(11) 0.0153(7) 0.0170(10) 0.0008(6) 0.0043(9) 0.0009(6)
C11 0.0177(12) 0.0158(8) 0.0204(11) -0.0010(6) 0.0016(10) 0.0004(6)
C13 0.0209(12) 0.0180(8) 0.0201(11) -0.0027(6) -0.0009(10) 0.0051(7)
C10 0.0156(11) 0.0159(7) 0.0172(10) -0.0031(6) 0.0036(9) -0.0019(6)
C12 0.0107(10) 0.0171(8) 0.0179(10) -0.0010(6) 0.0009(9) 0.0010(6)
C9 0.0170(11) 0.0175(8) 0.0150(10) 0.0004(6) -0.0003(9) 0.0008(7)
O3 0.0190(9) 0.0262(7) 0.0196(8) 0.0002(5) 0.0047(7) -0.0056(5)
O4 0.0125(8) 0.0171(6) 0.0216(8) 0.0018(5) 0.0006(7) -0.0012(5)
C14 0.0126(11) 0.0158(7) 0.0188(10) 0.0012(6) 0.0010(9) 0.0013(6)
O7 0.0261(9) 0.0278(7) 0.0229(8) 0.0046(6) 0.0115(8) 0.0062(6)
C7 0.0148(11) 0.0166(8) 0.0118(9) -0.0014(6) 0.0000(9) 0.0003(6)
O6 0.0187(8) 0.0169(6) 0.0241(8) -0.0063(5) 0.0071(7) -0.0032(5)
O5 0.0168(8) 0.0219(7) 0.0343(9) -0.0083(6) 0.0091(8) -0.0043(5)
C15 0.0169(11) 0.0147(8) 0.0169(10) -0.0014(6) 0.0013(9) -0.0006(6)
C5 0.060(3) 0.0461(16) 0.087(3) 0.0400(18) 0.015(2) 0.0023(16)

_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 O5 2.0031(14) . ?
Co1 O7 2.0406(14) . ?
Co1 O2 2.1205(14) . ?
Co1 N1 2.1263(18) . ?
Co1 O3 2.1342(15) . ?
Co1 O4 2.2720(14) . ?
Co2 O6 2.0430(13) 3_775 ?
Co2 O6 2.0430(13) . ?
Co2 O4 2.1092(15) 3_775 ?
Co2 O4 2.1092(15) . ?
Co2 O2 2.1770(12) 3_775 ?
Co2 O2 2.1770(12) . ?
N1 C1 1.338(3) . ?
N1 C6 1.342(3) . ?
C1 C2 1.384(3) . ?
C2 C3 1.366(4) . ?
C3 C5 1.375(5) . ?
C6 C5 1.360(4) . ?
O1 C7 1.250(2) . ?
O2 C7 1.284(2) . ?
C8 C13 1.532(3) . ?
C8 C7 1.535(3) . ?
C8 C9 1.538(3) . ?
C11 C10 1.527(3) . ?
C11 C12 1.550(3) . ?
C13 C12 1.530(3) . ?
C10 C15 1.525(3) 1_545 ?
C10 C9 1.534(3) . ?
C12 C14 1.513(3) 4_676 ?
O3 C14 1.247(2) . ?
O4 C14 1.289(2) . ?
C14 C12 1.513(3) 4_575 ?
O6 C15 1.257(2) . ?
O5 C15 1.257(2) . ?
C15 C10 1.525(3) 1_565 ?

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 Co1 O7 103.16(7) . . ?
O5 Co1 O2 91.44(6) . . ?
O7 Co1 O2 97.54(6) . . ?
O5 Co1 N1 89.67(7) . . ?
O7 Co1 N1 92.98(6) . . ?
O2 Co1 N1 168.88(6) . . ?
O5 Co1 O3 156.11(6) . . ?
O7 Co1 O3 100.49(6) . . ?
O2 Co1 O3 88.71(6) . . ?
N1 Co1 O3 85.82(7) . . ?
O5 Co1 O4 96.76(5) . . ?
O7 Co1 O4 160.08(6) . . ?
O2 Co1 O4 81.77(5) . . ?
N1 Co1 O4 87.11(6) . . ?
O3 Co1 O4 59.63(5) . . ?
O6 Co2 O6 180.00(8) 3_775 . ?
O6 Co2 O4 92.64(6) 3_775 3_775 ?
O6 Co2 O4 87.36(6) . 3_775 ?
O6 Co2 O4 87.36(6) 3_775 . ?
O6 Co2 O4 92.64(6) . . ?
O4 Co2 O4 180.0 3_775 . ?
O6 Co2 O2 92.08(5) 3_775 3_775 ?
O6 Co2 O2 87.92(5) . 3_775 ?
O4 Co2 O2 84.32(5) 3_775 3_775 ?
O4 Co2 O2 95.68(5) . 3_775 ?
O6 Co2 O2 87.92(5) 3_775 . ?
O6 Co2 O2 92.08(5) . . ?
O4 Co2 O2 95.68(5) 3_775 . ?
O4 Co2 O2 84.32(5) . . ?
O2 Co2 O2 180.0 3_775 . ?
C1 N1 C6 117.5(2) . . ?
C1 N1 Co1 121.66(14) . . ?
C6 N1 Co1 119.25(17) . . ?
N1 C1 C2 122.5(2) . . ?
C3 C2 C1 119.1(3) . . ?
C2 C3 C5 118.5(3) . . ?
N1 C6 C5 122.6(3) . . ?
C7 O2 Co1 125.87(12) . . ?
C7 O2 Co2 137.43(11) . . ?
Co1 O2 Co2 92.67(5) . . ?
C13 C8 C7 110.28(15) . . ?
C13 C8 C9 110.88(15) . . ?
C7 C8 C9 108.48(17) . . ?
C10 C11 C12 111.33(15) . . ?
C12 C13 C8 113.48(15) . . ?
C15 C10 C11 107.94(15) 1_545 . ?
C15 C10 C9 111.38(17) 1_545 . ?
C11 C10 C9 110.76(15) . . ?
C14 C12 C13 112.36(15) 4_676 . ?
C14 C12 C11 106.59(15) 4_676 . ?
C13 C12 C11 110.38(17) . . ?
C10 C9 C8 111.57(17) . . ?
C14 O3 Co1 93.32(12) . . ?
C14 O4 Co2 124.29(12) . . ?
C14 O4 Co1 86.04(11) . . ?
Co2 O4 Co1 90.33(6) . . ?
O3 C14 O4 119.81(19) . . ?
O3 C14 C12 121.05(18) . 4_575 ?
O4 C14 C12 118.68(16) . 4_575 ?
O1 C7 O2 122.61(17) . . ?
O1 C7 C8 118.78(16) . . ?
O2 C7 C8 118.61(15) . . ?
C15 O6 Co2 130.68(12) . . ?
C15 O5 Co1 128.16(12) . . ?
O5 C15 O6 125.54(17) . . ?
O5 C15 C10 116.71(15) . 1_565 ?
O6 C15 C10 117.74(16) . 1_565 ?
C6 C5 C3 119.8(3) . . ?

_diffrn_measured_fraction_theta_max 1.00
_diffrn_reflns_theta_full        29.49
_diffrn_measured_fraction_theta_full 1.00
_refine_diff_density_max         0.669
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.074
_database_code_depnum_ccdc_archive 'CCDC 941541'