# Electronic Supplementary Material (ESI) for Chemical Communications
# 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_p110526e

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H19 Co3 N10 O12.50'
_chemical_formula_weight         680.14

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Fddd

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/4, -y+1/4, z'
'x, -y+1/4, -z+1/4'
'-x+1/4, y, -z+1/4'
'x, y+1/2, z+1/2'
'-x+1/4, -y+3/4, z+1/2'
'x, -y+3/4, -z+3/4'
'-x+1/4, y+1/2, -z+3/4'
'x+1/2, y, z+1/2'
'-x+3/4, -y+1/4, z+1/2'
'x+1/2, -y+1/4, -z+3/4'
'-x+3/4, y, -z+3/4'
'x+1/2, y+1/2, z'
'-x+3/4, -y+3/4, z'
'x+1/2, -y+3/4, -z+1/4'
'-x+3/4, y+1/2, -z+1/4'
'-x, -y, -z'
'x-1/4, y-1/4, -z'
'-x, y-1/4, z-1/4'
'x-1/4, -y, z-1/4'
'-x, -y+1/2, -z+1/2'
'x-1/4, y+1/4, -z+1/2'
'-x, y+1/4, z+1/4'
'x-1/4, -y+1/2, z+1/4'
'-x+1/2, -y, -z+1/2'
'x+1/4, y-1/4, -z+1/2'
'-x+1/2, y-1/4, z+1/4'
'x+1/4, -y, z+1/4'
'-x+1/2, -y+1/2, -z'
'x+1/4, y+1/4, -z'
'-x+1/2, y+1/4, z-1/4'
'x+1/4, -y+1/2, z-1/4'

_cell_length_a                   15.6139(8)
_cell_length_b                   18.3439(11)
_cell_length_c                   34.336(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     9834.5(11)
_cell_formula_units_Z            16
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2894
_cell_measurement_theta_min      2.6037
_cell_measurement_theta_max      29.1633

_exptl_crystal_description       rhombic
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.824
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             5392
_exptl_absorpt_coefficient_mu    2.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.64385
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   CRYSALISPRO

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6638
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_sigmaI/netI    0.0597
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2174
_reflns_number_gt                1675
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CRYSALISPRO
_computing_cell_refinement       CRYSALISPRO
_computing_data_reduction        CRYSALISPRO
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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. 
DFIX 0.85 O5 H6
The distance between O5 and H6 is bundled in the normal range by 
the DFIX instruction.
;

_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^)+(0.0766P)^2^+80.6320P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2174
_refine_ls_number_parameters     188
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1574
_refine_ls_wR_factor_gt          0.1473
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_restrained_S_all      1.127
_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 0.50379(5) 0.61040(4) 0.48158(2) 0.0171(3) Uani 1 1 d . . .
Co2 Co 0.8750 0.3750 0.56079(3) 0.0193(3) Uani 1 2 d S . .
N3 N 0.6760(3) 0.5568(3) 0.50860(15) 0.0207(12) Uani 1 1 d . . .
O4 O 0.8323(3) 0.5892(2) 0.52589(14) 0.0277(11) Uani 1 1 d . . .
C3 C 0.7201(4) 0.5055(3) 0.52759(18) 0.0192(13) Uani 1 1 d . . .
C4 C 0.8093(4) 0.5272(3) 0.53810(19) 0.0222(14) Uani 1 1 d . . .
O1 O 0.7407(2) 0.3483(2) 0.56220(13) 0.0251(10) Uani 1 1 d . . .
O2 O 0.6002(3) 0.3416(2) 0.55570(13) 0.0256(10) Uani 1 1 d . . .
N1 N 0.5880(3) 0.4692(2) 0.52115(15) 0.0184(11) Uani 1 1 d . . .
O3 O 0.8543(3) 0.4873(2) 0.55976(14) 0.0306(11) Uani 1 1 d . . .
C1 C 0.6700(4) 0.3738(3) 0.55281(17) 0.0172(12) Uani 1 1 d . . .
N2 N 0.5957(3) 0.5348(2) 0.50529(15) 0.0209(12) Uani 1 1 d . . .
C2 C 0.6645(3) 0.4488(3) 0.53534(18) 0.0185(13) Uani 1 1 d . . .
N5 N 0.8750 0.3750 0.6209(2) 0.0218(16) Uani 1 2 d S . .
O5 O 0.8750 0.3750 0.5007(2) 0.053(2) Uani 1 2 d SD . .
N4 N 0.8310(3) 0.3802(3) 0.68250(15) 0.0239(12) Uani 1 1 d . . .
C5 C 0.8093(4) 0.3834(3) 0.64594(17) 0.0226(14) Uani 1 1 d . . .
H5A H 0.7531 0.3909 0.6378 0.027 Uiso 1 1 calc R . .
O6 O 0.7677(4) 0.3076(3) 0.45192(19) 0.0513(15) Uani 1 1 d G . .
H6A H 0.7900 0.2670 0.4458 0.077 Uiso 1 1 d G . .
H6B H 0.7251 0.3004 0.4669 0.077 Uiso 1 1 d G . .
O7 O 0.3750 0.7590(4) 0.3750 0.074(3) Uani 1 2 d S . .
N6 N 0.7380(8) 0.3750 0.3750 0.077(4) Uani 1 2 d S . .
H6C H 0.7718 0.3533 0.3928 0.092 Uiso 0.50 1 calc PR . .
H6D H 0.7718 0.3967 0.3572 0.092 Uiso 0.50 1 calc PR . .
C6 C 0.6830(8) 0.4309(8) 0.3945(4) 0.114(5) Uani 1 1 d . . .
H6E H 0.6566 0.4612 0.3751 0.171 Uiso 1 1 calc R . .
H6F H 0.7176 0.4604 0.4114 0.171 Uiso 1 1 calc R . .
H6G H 0.6395 0.4069 0.4095 0.171 Uiso 1 1 calc R . .
O8 O 0.6250 0.4722(15) 0.6250 0.030(6) Uani 0.25 2 d SP . .
O9 O 0.6250 0.5988(14) 0.6250 0.071(13) Uani 0.25 2 d SP . .
H6 H 0.843(4) 0.353(4) 0.4841(16) 0.05(2) Uiso 1 1 d 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 0.0133(4) 0.0139(4) 0.0243(5) 0.0002(3) 0.0000(3) -0.0022(3)
Co2 0.0171(6) 0.0187(6) 0.0221(6) 0.000 0.000 -0.0015(5)
N3 0.014(2) 0.015(2) 0.033(3) 0.005(2) -0.006(2) -0.004(2)
O4 0.023(2) 0.018(2) 0.042(3) 0.008(2) -0.007(2) -0.0075(18)
C3 0.019(3) 0.011(3) 0.028(3) 0.002(3) 0.000(3) -0.002(2)
C4 0.020(3) 0.017(3) 0.029(3) -0.001(3) 0.000(3) 0.001(3)
O1 0.017(2) 0.019(2) 0.039(3) 0.006(2) 0.001(2) 0.0028(18)
O2 0.020(2) 0.019(2) 0.038(3) 0.009(2) 0.001(2) -0.0030(18)
N1 0.016(2) 0.011(2) 0.028(3) 0.002(2) -0.002(2) -0.0010(19)
O3 0.024(2) 0.020(2) 0.048(3) 0.008(2) -0.014(2) -0.0002(19)
C1 0.016(3) 0.015(3) 0.020(3) 0.001(3) -0.006(3) -0.002(2)
N2 0.014(2) 0.014(2) 0.035(3) 0.006(2) -0.005(2) -0.003(2)
C2 0.014(3) 0.019(3) 0.023(3) 0.002(3) 0.001(3) -0.002(2)
N5 0.020(4) 0.028(4) 0.018(4) 0.000 0.000 0.001(3)
O5 0.056(5) 0.081(6) 0.021(4) 0.000 0.000 -0.044(5)
N4 0.015(2) 0.031(3) 0.026(3) -0.002(3) 0.000(2) 0.003(2)
C5 0.016(3) 0.028(3) 0.023(3) -0.001(3) -0.003(3) 0.004(3)
O6 0.043(3) 0.047(3) 0.064(4) -0.002(3) -0.005(3) -0.015(3)
O7 0.099(7) 0.044(5) 0.078(6) 0.000 0.026(6) 0.000
N6 0.073(8) 0.074(8) 0.082(9) 0.029(8) 0.000 0.000
C6 0.121(11) 0.112(11) 0.110(11) 0.038(9) 0.029(10) 0.030(9)
O8 0.028(13) 0.050(16) 0.011(11) 0.000 -0.004(11) 0.000
O9 0.18(4) 0.021(14) 0.017(13) 0.000 0.02(2) 0.000

_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 N1 2.048(5) 17_666 ?
Co1 N4 2.079(5) 20_565 ?
Co1 N3 2.091(5) 2_665 ?
Co1 N2 2.156(5) . ?
Co1 O4 2.230(4) 2_665 ?
Co1 O2 2.247(4) 17_666 ?
Co2 N5 2.063(7) . ?
Co2 O5 2.063(7) . ?
Co2 O3 2.085(4) 14_655 ?
Co2 O3 2.085(4) . ?
Co2 O1 2.155(4) . ?
Co2 O1 2.155(4) 14_655 ?
N3 N2 1.321(6) . ?
N3 C3 1.336(7) . ?
N3 Co1 2.091(5) 2_665 ?
O4 C4 1.264(7) . ?
O4 Co1 2.230(4) 2_665 ?
C3 C2 1.381(8) . ?
C3 C4 1.492(8) . ?
C4 O3 1.258(7) . ?
O1 C1 1.241(7) . ?
O2 C1 1.244(7) . ?
O2 Co1 2.247(4) 17_666 ?
N1 N2 1.327(6) . ?
N1 C2 1.343(7) . ?
N1 Co1 2.048(5) 17_666 ?
C1 C2 1.503(8) . ?
N5 C5 1.348(7) . ?
N5 C5 1.348(7) 14_655 ?
O5 H6 0.86(2) . ?
N4 C5 1.302(8) . ?
N4 N4 1.387(10) 14_655 ?
N4 Co1 2.079(5) 28_565 ?
C5 H5A 0.9300 . ?
O6 H6A 0.8498 . ?
O6 H6B 0.8505 . ?
N6 C6 1.496(13) . ?
N6 C6 1.496(13) 7 ?
N6 H6C 0.9000 . ?
N6 H6D 0.9000 . ?
C6 H6E 0.9600 . ?
C6 H6F 0.9600 . ?
C6 H6G 0.9600 . ?
O9 O9 0.96(5) 2_665 ?

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
N1 Co1 N4 115.3(2) 17_666 20_565 ?
N1 Co1 N3 154.9(2) 17_666 2_665 ?
N4 Co1 N3 89.7(2) 20_565 2_665 ?
N1 Co1 N2 91.41(18) 17_666 . ?
N4 Co1 N2 88.5(2) 20_565 . ?
N3 Co1 N2 87.17(18) 2_665 . ?
N1 Co1 O4 84.57(17) 17_666 2_665 ?
N4 Co1 O4 150.20(19) 20_565 2_665 ?
N3 Co1 O4 73.26(17) 2_665 2_665 ?
N2 Co1 O4 114.23(19) . 2_665 ?
N1 Co1 O2 75.40(17) 17_666 17_666 ?
N4 Co1 O2 85.68(18) 20_565 17_666 ?
N3 Co1 O2 110.29(17) 2_665 17_666 ?
N2 Co1 O2 161.51(18) . 17_666 ?
O4 Co1 O2 77.93(17) 2_665 17_666 ?
N5 Co2 O5 180.000(1) . . ?
N5 Co2 O3 90.98(13) . 14_655 ?
O5 Co2 O3 89.02(13) . 14_655 ?
N5 Co2 O3 90.98(13) . . ?
O5 Co2 O3 89.02(13) . . ?
O3 Co2 O3 178.0(3) 14_655 . ?
N5 Co2 O1 88.72(12) . . ?
O5 Co2 O1 91.28(12) . . ?
O3 Co2 O1 85.80(16) 14_655 . ?
O3 Co2 O1 94.25(16) . . ?
N5 Co2 O1 88.72(12) . 14_655 ?
O5 Co2 O1 91.28(12) . 14_655 ?
O3 Co2 O1 94.25(16) 14_655 14_655 ?
O3 Co2 O1 85.80(16) . 14_655 ?
O1 Co2 O1 177.4(2) . 14_655 ?
N2 N3 C3 108.5(5) . . ?
N2 N3 Co1 132.9(4) . 2_665 ?
C3 N3 Co1 117.2(4) . 2_665 ?
C4 O4 Co1 115.4(4) . 2_665 ?
N3 C3 C2 107.4(5) . . ?
N3 C3 C4 114.3(5) . . ?
C2 C3 C4 137.8(6) . . ?
O3 C4 O4 124.2(6) . . ?
O3 C4 C3 120.6(5) . . ?
O4 C4 C3 115.1(5) . . ?
C1 O1 Co2 140.7(4) . . ?
C1 O2 Co1 113.7(4) . 17_666 ?
N2 N1 C2 108.7(4) . . ?
N2 N1 Co1 133.8(4) . 17_666 ?
C2 N1 Co1 116.1(4) . 17_666 ?
C4 O3 Co2 132.2(4) . . ?
O1 C1 O2 125.4(5) . . ?
O1 C1 C2 120.0(5) . . ?
O2 C1 C2 114.6(5) . . ?
N3 N2 N1 109.1(4) . . ?
N3 N2 Co1 117.9(3) . . ?
N1 N2 Co1 132.7(4) . . ?
N1 C2 C3 106.2(5) . . ?
N1 C2 C1 116.8(5) . . ?
C3 C2 C1 136.9(5) . . ?
C5 N5 C5 100.7(7) . 14_655 ?
C5 N5 Co2 129.7(3) . . ?
C5 N5 Co2 129.7(3) 14_655 . ?
Co2 O5 H6 132(5) . . ?
C5 N4 N4 105.3(3) . 14_655 ?
C5 N4 Co1 128.8(4) . 28_565 ?
N4 N4 Co1 125.84(14) 14_655 28_565 ?
N4 C5 N5 114.3(5) . . ?
N4 C5 H5A 122.8 . . ?
N5 C5 H5A 122.8 . . ?
H6A O6 H6B 109.5 . . ?
C6 N6 C6 109.9(14) . 7 ?
C6 N6 H6C 109.7 . . ?
C6 N6 H6C 109.7 7 . ?
C6 N6 H6D 109.7 . . ?
C6 N6 H6D 109.7 7 . ?
H6C N6 H6D 108.2 . . ?
N6 C6 H6E 109.5 . . ?
N6 C6 H6F 109.5 . . ?
H6E C6 H6F 109.5 . . ?
N6 C6 H6G 109.5 . . ?
H6E C6 H6G 109.5 . . ?
H6F C6 H6G 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.263
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.148
_database_code_depnum_ccdc_archive 'CCDC 909522'