# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_compound-2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H6 Co N10'
_chemical_formula_weight         349.20

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           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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'
'-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                   13.9353(14)
_cell_length_b                   8.9922(9)
_cell_length_c                   20.379(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2553.6(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.816
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1400
_exptl_absorpt_coefficient_mu    1.362
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6878
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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            20111
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         29.60
_reflns_number_total             3582
_reflns_number_gt                2562
_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)+(0.0661P)²+1.2267P] where P=(Fo²+2Fc²)/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         3582
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1303
_refine_ls_wR_factor_gt          0.1178
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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 0.59595(3) 0.16446(4) 0.331702(18) 0.02645(13) Uani 1 1 d . . .
N1 N 0.47284(17) 0.0409(2) 0.35749(11) 0.0260(5) Uani 1 1 d . . .
C9 C 0.5890(2) 0.3838(4) 0.52106(15) 0.0346(7) Uani 1 1 d . . .
H9 H 0.6264 0.4551 0.5421 0.042 Uiso 1 1 calc R . .
N2 N 0.55854(18) 0.2303(2) 0.42836(10) 0.0276(5) Uani 1 1 d . . .
C6 C 0.4810(2) 0.1732(3) 0.45710(13) 0.0281(6) Uani 1 1 d . . .
C10 C 0.6116(2) 0.3359(3) 0.45768(14) 0.0299(6) Uani 1 1 d . . .
C1 C 0.4355(2) -0.0537(3) 0.31330(13) 0.0277(6) Uani 1 1 d . . .
C4 C 0.3445(2) -0.0091(3) 0.43051(13) 0.0328(6) Uani 1 1 d . . .
H4 H 0.3147 0.0060 0.4708 0.039 Uiso 1 1 calc R . .
C2 C 0.3505(2) -0.1287(3) 0.32483(14) 0.0328(6) Uani 1 1 d . . .
H2 H 0.3246 -0.1927 0.2936 0.039 Uiso 1 1 calc R . .
C3 C 0.3053(2) -0.1053(4) 0.38456(14) 0.0341(6) Uani 1 1 d . . .
H3 H 0.2482 -0.1544 0.3939 0.041 Uiso 1 1 calc R . .
C5 C 0.4289(2) 0.0638(3) 0.41518(13) 0.0263(5) Uani 1 1 d . . .
C8 C 0.5109(2) 0.3236(3) 0.55147(14) 0.0379(7) Uani 1 1 d . . .
H8 H 0.4957 0.3532 0.5940 0.045 Uiso 1 1 calc R . .
C7 C 0.4533(2) 0.2185(3) 0.51997(13) 0.0331(6) Uani 1 1 d . . .
H7 H 0.3987 0.1801 0.5400 0.040 Uiso 1 1 calc R . .
N7 N 0.69855(18) 0.3254(3) 0.35501(13) 0.0327(5) Uani 1 1 d . . .
C11 C 0.4966(2) -0.0608(3) 0.25355(13) 0.0275(5) Uani 1 1 d . . .
N3 N 0.56781(18) 0.0361(2) 0.24750(11) 0.0281(5) Uani 1 1 d . . .
C12 C 0.6881(2) 0.3900(3) 0.41389(14) 0.0306(6) Uani 1 1 d . . .
N6 N 0.49261(17) -0.1546(2) 0.20367(11) 0.0274(5) Uani 1 1 d . . .
N10 N 0.75039(19) 0.5017(3) 0.42100(12) 0.0356(6) Uani 1 1 d . . .
N5 N 0.5676(2) -0.1115(3) 0.16444(12) 0.0344(5) Uani 1 1 d . . .
N8 N 0.7714(2) 0.3957(3) 0.32441(13) 0.0370(6) Uani 1 1 d . . .
N9 N 0.80270(19) 0.5009(3) 0.36375(12) 0.0343(6) Uani 1 1 d . . .
N4 N 0.61186(19) 0.0017(3) 0.19050(13) 0.0370(6) Uani 1 1 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 N7 2.089(2) . ?
Co1 N3 2.105(2) . ?
Co1 N1 2.111(2) . ?
Co1 N2 2.122(2) . ?
Co1 N9 2.141(3) 8_755 ?
Co1 N6 2.165(2) 3_655 ?
N1 C5 1.341(3) . ?
N1 C1 1.344(4) . ?
C9 C8 1.364(4) . ?
C9 C10 1.398(4) . ?
N2 C6 1.333(4) . ?
N2 C10 1.344(4) . ?
C6 C7 1.398(4) . ?
C6 C5 1.491(4) . ?
C10 C12 1.473(4) . ?
C1 C2 1.383(4) . ?
C1 C11 1.487(4) . ?
C4 C5 1.382(4) . ?
C4 C3 1.387(4) . ?
C2 C3 1.387(4) . ?
C8 C7 1.397(4) . ?
N7 C12 1.341(4) . ?
N7 N8 1.349(3) . ?
C11 N6 1.322(3) . ?
C11 N3 1.326(4) . ?
N3 N4 1.350(3) . ?
C12 N10 1.335(4) . ?
N6 N5 1.371(3) . ?
N6 Co1 2.165(2) 3_645 ?
N10 N9 1.376(3) . ?
N5 N4 1.303(4) . ?
N8 N9 1.315(3) . ?
N9 Co1 2.141(3) 8_765 ?

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
N7 Co1 N3 133.85(10) . . ?
N7 Co1 N1 149.82(9) . . ?
N3 Co1 N1 76.28(9) . . ?
N7 Co1 N2 76.34(10) . . ?
N3 Co1 N2 149.77(10) . . ?
N1 Co1 N2 73.50(9) . . ?
N7 Co1 N9 87.42(10) . 8_755 ?
N3 Co1 N9 89.70(9) . 8_755 ?
N1 Co1 N9 95.66(9) . 8_755 ?
N2 Co1 N9 94.05(9) . 8_755 ?
N7 Co1 N6 86.87(10) . 3_655 ?
N3 Co1 N6 91.98(9) . 3_655 ?
N1 Co1 N6 90.87(9) . 3_655 ?
N2 Co1 N6 87.67(8) . 3_655 ?
N9 Co1 N6 173.47(9) 8_755 3_655 ?
C5 N1 C1 120.5(3) . . ?
C5 N1 Co1 120.55(19) . . ?
C1 N1 Co1 118.78(18) . . ?
C8 C9 C10 118.5(3) . . ?
C6 N2 C10 121.6(2) . . ?
C6 N2 Co1 119.99(18) . . ?
C10 N2 Co1 118.3(2) . . ?
N2 C6 C7 120.9(3) . . ?
N2 C6 C5 113.4(2) . . ?
C7 C6 C5 125.7(3) . . ?
N2 C10 C9 120.3(3) . . ?
N2 C10 C12 111.2(2) . . ?
C9 C10 C12 128.4(3) . . ?
N1 C1 C2 121.8(3) . . ?
N1 C1 C11 110.7(2) . . ?
C2 C1 C11 127.5(3) . . ?
C5 C4 C3 118.6(3) . . ?
C1 C2 C3 117.6(3) . . ?
C2 C3 C4 120.6(3) . . ?
N1 C5 C4 120.9(3) . . ?
N1 C5 C6 112.4(2) . . ?
C4 C5 C6 126.7(2) . . ?
C9 C8 C7 121.2(3) . . ?
C8 C7 C6 117.4(3) . . ?
C12 N7 N8 107.0(2) . . ?
C12 N7 Co1 115.4(2) . . ?
N8 N7 Co1 137.3(2) . . ?
N6 C11 N3 112.3(2) . . ?
N6 C11 C1 129.3(3) . . ?
N3 C11 C1 118.4(2) . . ?
C11 N3 N4 105.7(2) . . ?
C11 N3 Co1 115.08(18) . . ?
N4 N3 Co1 137.94(19) . . ?
N10 C12 N7 110.7(3) . . ?
N10 C12 C10 130.7(3) . . ?
N7 C12 C10 118.5(3) . . ?
C11 N6 N5 103.6(2) . . ?
C11 N6 Co1 139.38(19) . 3_645 ?
N5 N6 Co1 116.91(16) . 3_645 ?
C12 N10 N9 104.4(2) . . ?
N4 N5 N6 110.1(2) . . ?
N9 N8 N7 107.8(2) . . ?
N8 N9 N10 110.2(2) . . ?
N8 N9 Co1 121.8(2) . 8_765 ?
N10 N9 Co1 127.22(18) . 8_765 ?
N5 N4 N3 108.3(2) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        29.60
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.649
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.089
_database_code_depnum_ccdc_archive 'CCDC 1008389'
