# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_293K
_database_code_depnum_ccdc_archive 'CCDC 1012553'
_audit_update_record             
;
2014-07-07 deposited with the CCDC.
2015-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 Co K N10'
_chemical_formula_weight         392.33

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'
K K 0.2009 0.2494 '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           Trigonal
_symmetry_space_group_name_H-M   R-3m

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

_cell_length_a                   8.7151(12)
_cell_length_b                   8.7151(12)
_cell_length_c                   19.011(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     1250.5(3)
_cell_formula_units_Z            3
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5469
_cell_measurement_theta_min      3.22
_cell_measurement_theta_max      27.55

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             594
_exptl_absorpt_coefficient_mu    1.296
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8633
_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         'Sealed Tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       
;
Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4284
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_av_sigmaI/netI    0.0330
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.21
_diffrn_reflns_theta_max         27.36
_reflns_number_total             387
_reflns_number_gt                375
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'

_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)+(0.0567P)²+0.6586P] 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         387
_refine_ls_number_parameters     29
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0969
_refine_ls_wR_factor_gt          0.0950
_refine_ls_goodness_of_fit_ref   1.327
_refine_ls_restrained_S_all      1.327
_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 0.6667 0.3333 0.3333 0.0191(3) Uani 1 12 d S . .
K1 K 1.0000 1.0000 0.5000 0.0280(4) Uani 1 12 d S . .
N1 N 0.83424(14) 0.6685(3) 0.42266(11) 0.0486(8) Uani 1 2 d S . .
C1 C 0.77042(15) 0.5408(3) 0.39003(11) 0.0281(5) Uani 1 2 d S . .
C2 C 0.1916(7) 0.5958(3) 0.4180(3) 0.084(2) Uani 0.83 2 d SP . .
H2A H 0.0685 0.5343 0.4160 0.101 Uiso 0.83 2 calc SPR . .
C3 C 0.2624(3) 0.7376(3) 0.4192(3) 0.090(2) Uani 0.83 2 d SP . .
H3A H 0.2009 0.7991 0.4211 0.108 Uiso 0.83 2 calc SPR . .

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 0.0180(3) 0.0180(3) 0.0215(4) 0.000 0.000 0.00898(17)
K1 0.0260(5) 0.0260(5) 0.0321(7) 0.000 0.000 0.0130(2)
N1 0.0572(15) 0.0339(16) 0.0470(15) -0.0132(13) -0.0066(6) 0.0169(8)
C1 0.0277(9) 0.0280(11) 0.0288(11) -0.0005(9) -0.0002(4) 0.0140(6)
C2 0.027(2) 0.121(5) 0.071(3) -0.0037(11) -0.007(2) 0.0136(11)
C3 0.138(5) 0.138(5) 0.068(3) -0.0004(11) 0.0004(11) 0.124(5)

_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 C1 1.901(2) 31_655 ?
Co1 C1 1.901(2) 32 ?
Co1 C1 1.901(2) 3_665 ?
Co1 C1 1.901(2) 33_545 ?
Co1 C1 1.901(2) . ?
Co1 C1 1.901(2) 2_655 ?
K1 N1 2.902(2) 19_776 ?
K1 N1 2.902(2) . ?
K1 N1 2.902(2) 21_656 ?
K1 N1 2.902(2) 20_566 ?
K1 N1 2.902(2) 2_765 ?
K1 N1 2.902(2) 3_675 ?
N1 C1 1.146(3) . ?
C2 C3 1.070(4) . ?
C2 C3 1.070(4) 2_665 ?
C2 C2 1.852(9) 3_565 ?
C2 C2 1.852(9) 2_665 ?
C3 C2 1.070(4) 3_565 ?
C3 C3 1.854(9) 3_565 ?
C3 C3 1.854(9) 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
C1 Co1 C1 91.02(9) 31_655 32 ?
C1 Co1 C1 88.98(9) 31_655 3_665 ?
C1 Co1 C1 88.98(9) 32 3_665 ?
C1 Co1 C1 91.02(9) 31_655 33_545 ?
C1 Co1 C1 91.02(9) 32 33_545 ?
C1 Co1 C1 180.0 3_665 33_545 ?
C1 Co1 C1 180.0 31_655 . ?
C1 Co1 C1 88.98(9) 32 . ?
C1 Co1 C1 91.02(9) 3_665 . ?
C1 Co1 C1 88.98(9) 33_545 . ?
C1 Co1 C1 88.98(9) 31_655 2_655 ?
C1 Co1 C1 180.0 32 2_655 ?
C1 Co1 C1 91.02(9) 3_665 2_655 ?
C1 Co1 C1 88.98(9) 33_545 2_655 ?
C1 Co1 C1 91.02(9) . 2_655 ?
N1 K1 N1 180.0 19_776 . ?
N1 K1 N1 96.60(6) 19_776 21_656 ?
N1 K1 N1 83.40(6) . 21_656 ?
N1 K1 N1 96.60(6) 19_776 20_566 ?
N1 K1 N1 83.40(6) . 20_566 ?
N1 K1 N1 96.60(6) 21_656 20_566 ?
N1 K1 N1 83.40(6) 19_776 2_765 ?
N1 K1 N1 96.60(6) . 2_765 ?
N1 K1 N1 83.40(6) 21_656 2_765 ?
N1 K1 N1 180.0 20_566 2_765 ?
N1 K1 N1 83.40(6) 19_776 3_675 ?
N1 K1 N1 96.60(6) . 3_675 ?
N1 K1 N1 180.0 21_656 3_675 ?
N1 K1 N1 83.40(6) 20_566 3_675 ?
N1 K1 N1 96.60(6) 2_765 3_675 ?
C1 N1 K1 177.66(19) . . ?
N1 C1 Co1 178.2(2) . . ?
C3 C2 C3 120.0(6) . 2_665 ?
C3 C2 C2 30.1(3) . 3_565 ?
C3 C2 C2 90.0(3) 2_665 3_565 ?
C3 C2 C2 90.0(3) . 2_665 ?
C3 C2 C2 30.1(3) 2_665 2_665 ?
C2 C2 C2 60.000(1) 3_565 2_665 ?
C2 C3 C2 119.9(6) . 3_565 ?
C2 C3 C3 90.0(3) . 3_565 ?
C2 C3 C3 30.0(3) 3_565 3_565 ?
C2 C3 C3 30.0(3) . 2_665 ?
C2 C3 C3 90.0(3) 3_565 2_665 ?
C3 C3 C3 60.000(2) 3_565 2_665 ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.36
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.567
_refine_diff_density_min         -0.760
_refine_diff_density_rms         0.223

# start Validation Reply Form
_vrf_PLAT773_a                   
;
PROBLEM: Suspect C-C Bond in CIF:   C2     --  C2      ..       1.85 Ang. 
RESPONSE: The imidazolium cation is disordered.
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_148K
_database_code_depnum_ccdc_archive 'CCDC 1012554'
_audit_update_record             
;
2014-07-07 deposited with the CCDC.
2015-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 Co K N10'
_chemical_formula_weight         392.33

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'
K K 0.2009 0.2494 '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           Trigonal
_symmetry_space_group_name_H-M   R-3m

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

_cell_length_a                   8.738(6)
_cell_length_b                   8.738(6)
_cell_length_c                   18.709(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     1237.0(13)
_cell_formula_units_Z            3
_cell_measurement_temperature    148(2)
_cell_measurement_reflns_used    1325
_cell_measurement_theta_min      2.9021
_cell_measurement_theta_max      27.4584

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             594
_exptl_absorpt_coefficient_mu    1.310
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8286
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      148(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            4456
_diffrn_reflns_av_R_equivalents  0.0759
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.27
_diffrn_reflns_theta_max         27.44
_reflns_number_total             381
_reflns_number_gt                369
_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)+(0.0169P)²+23.2302P] 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         381
_refine_ls_number_parameters     26
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0589
_refine_ls_wR_factor_ref         0.1399
_refine_ls_wR_factor_gt          0.1393
_refine_ls_goodness_of_fit_ref   1.255
_refine_ls_restrained_S_all      1.255
_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 1.0000 1.0000 0.5000 0.0093(5) Uani 1 12 d S . .
K1 K 0.6667 0.3333 0.3333 0.0154(6) Uani 1 12 d S . .
N1 N 0.8325(4) 0.6651(7) 0.4100(3) 0.0364(14) Uani 1 2 d S . .
C1 C 0.8962(4) 0.7923(7) 0.4427(3) 0.0190(11) Uani 1 2 d S . .
C2 C 0.2090(8) 0.6660(10) 0.4145(3) 0.081(3) Uani 1 1 d . . .
H2 H 0.1026 0.6660 0.4145 0.098 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 0.0079(6) 0.0079(6) 0.0120(8) 0.000 0.000 0.0040(3)
K1 0.0157(9) 0.0157(9) 0.0148(12) 0.000 0.000 0.0078(4)
N1 0.052(3) 0.018(3) 0.028(2) -0.006(2) -0.0032(11) 0.0089(13)
C1 0.022(2) 0.020(3) 0.014(2) 0.002(2) 0.0008(10) 0.0101(13)
C2 0.060(4) 0.175(9) 0.049(3) -0.001(3) 0.002(3) 0.089(6)

_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 C1 1.902(5) 19_776 ?
Co1 C1 1.902(5) . ?
Co1 C1 1.902(5) 2_765 ?
Co1 C1 1.902(5) 20_566 ?
Co1 C1 1.902(5) 21_656 ?
Co1 C1 1.902(5) 3_675 ?
K1 N1 2.891(5) 33_545 ?
K1 N1 2.891(5) 3_665 ?
K1 N1 2.891(5) . ?
K1 N1 2.891(5) 2_655 ?
K1 N1 2.891(5) 31_655 ?
K1 N1 2.891(5) 32 ?
N1 C1 1.141(7) . ?
C2 C2 1.075(14) 24_565 ?
C2 C2 1.092(14) 22_665 ?
C2 C2 1.877(10) 3_565 ?
C2 C2 1.877(10) 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
C1 Co1 C1 180.000(1) 19_776 . ?
C1 Co1 C1 88.6(2) 19_776 2_765 ?
C1 Co1 C1 91.4(2) . 2_765 ?
C1 Co1 C1 91.4(2) 19_776 20_566 ?
C1 Co1 C1 88.6(2) . 20_566 ?
C1 Co1 C1 180.000(1) 2_765 20_566 ?
C1 Co1 C1 91.4(2) 19_776 21_656 ?
C1 Co1 C1 88.6(2) . 21_656 ?
C1 Co1 C1 88.6(2) 2_765 21_656 ?
C1 Co1 C1 91.4(2) 20_566 21_656 ?
C1 Co1 C1 88.6(2) 19_776 3_675 ?
C1 Co1 C1 91.4(2) . 3_675 ?
C1 Co1 C1 91.4(2) 2_765 3_675 ?
C1 Co1 C1 88.6(2) 20_566 3_675 ?
C1 Co1 C1 180.0(2) 21_656 3_675 ?
N1 K1 N1 180.0 33_545 3_665 ?
N1 K1 N1 82.48(14) 33_545 . ?
N1 K1 N1 97.52(14) 3_665 . ?
N1 K1 N1 82.48(14) 33_545 2_655 ?
N1 K1 N1 97.52(14) 3_665 2_655 ?
N1 K1 N1 97.52(14) . 2_655 ?
N1 K1 N1 97.52(14) 33_545 31_655 ?
N1 K1 N1 82.48(14) 3_665 31_655 ?
N1 K1 N1 180.0 . 31_655 ?
N1 K1 N1 82.48(14) 2_655 31_655 ?
N1 K1 N1 97.52(14) 33_545 32 ?
N1 K1 N1 82.48(14) 3_665 32 ?
N1 K1 N1 82.48(14) . 32 ?
N1 K1 N1 180.0 2_655 32 ?
N1 K1 N1 97.52(14) 31_655 32 ?
C1 N1 K1 177.3(5) . . ?
N1 C1 Co1 178.2(5) . . ?
C2 C2 C2 120.000(5) 24_565 22_665 ?
C2 C2 C2 90.3(4) 24_565 3_565 ?
C2 C2 C2 29.7(4) 22_665 3_565 ?
C2 C2 C2 30.3(4) 24_565 2_665 ?
C2 C2 C2 89.7(4) 22_665 2_665 ?
C2 C2 C2 60.000(1) 3_565 2_665 ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.44
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.738
_refine_diff_density_min         -0.608
_refine_diff_density_rms         0.125

# start Validation Reply Form
_vrf_PLAT773_a                   
;
PROBLEM: Small Average Phenyl   C-C Dist. C2     -C2_*          1.08 Ang.
RESPONSE: The imidazolium cation is disordered.
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_93K
_database_code_depnum_ccdc_archive 'CCDC 1012555'
_audit_update_record             
;
2014-07-07 deposited with the CCDC.
2015-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 Co K N10'
_chemical_formula_weight         392.33

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'
K K 0.2009 0.2494 '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   C2/c

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

_cell_length_a                   13.427(3)
_cell_length_b                   8.7318(17)
_cell_length_c                   15.083(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.70(3)
_cell_angle_gamma                90.00
_cell_volume                     1643.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    2296
_cell_measurement_theta_min      2.8457
_cell_measurement_theta_max      27.5631

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    1.315
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9135
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      93(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            8543
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0166
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.85
_diffrn_reflns_theta_max         27.41
_reflns_number_total             1861
_reflns_number_gt                1649
_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)+(0.0241P)²+23.9816P] 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         1861
_refine_ls_number_parameters     111
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0614
_refine_ls_wR_factor_ref         0.1311
_refine_ls_wR_factor_gt          0.1286
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.113
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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 0.7500 0.2500 0.5000 0.00501(19) Uani 1 2 d S . .
K1 K 0.5000 0.25132(13) 0.7500 0.0108(2) Uani 1 2 d S . .
N1 N 0.6148(3) 0.2226(5) 0.6232(3) 0.0299(9) Uani 1 1 d . . .
N2 N 0.8825(3) 0.4921(5) 0.6410(3) 0.0305(9) Uani 1 1 d . . .
N3 N 0.8821(3) -0.0164(5) 0.6160(3) 0.0309(9) Uani 1 1 d . . .
N4 N 0.8782(3) 0.2114(6) 0.9467(3) 0.0395(12) Uani 1 1 d . . .
H4 H 0.8778 0.1796 1.0005 0.047 Uiso 1 1 calc R . .
N5 N 0.8816(3) 0.3565(5) 0.8379(4) 0.0420(13) Uani 1 1 d . . .
H5 H 0.8834 0.4375 0.8061 0.050 Uiso 1 1 calc R . .
C1 C 0.6639(3) 0.2354(5) 0.5753(3) 0.0161(8) Uani 1 1 d . . .
C2 C 0.8349(3) 0.4004(5) 0.5871(3) 0.0181(8) Uani 1 1 d . . .
C3 C 0.8354(3) 0.0876(5) 0.5743(3) 0.0162(8) Uani 1 1 d . . .
C6 C 0.8811(4) 0.3517(7) 0.9236(5) 0.0436(15) Uani 1 1 d . . .
H6 H 0.8826 0.4359 0.9618 0.052 Uiso 1 1 calc R . .
C7 C 0.8761(4) 0.1214(5) 0.8738(5) 0.0410(14) Uani 1 1 d . . .
H7 H 0.8731 0.0150 0.8726 0.049 Uiso 1 1 calc R . .
C8 C 0.8787(4) 0.2067(8) 0.8074(3) 0.0439(16) Uani 1 1 d . . .
H8 H 0.8787 0.1747 0.7486 0.053 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 0.0070(3) 0.0044(3) 0.0043(3) 0.0001(2) 0.0029(2) 0.0001(2)
K1 0.0113(5) 0.0111(5) 0.0103(5) 0.000 0.0043(4) 0.000
N1 0.0234(19) 0.053(3) 0.0173(17) 0.0087(17) 0.0125(15) 0.0135(18)
N2 0.0227(19) 0.0212(19) 0.041(2) -0.0155(17) 0.0047(17) -0.0015(16)
N3 0.0226(19) 0.030(2) 0.037(2) 0.0193(18) 0.0079(17) 0.0060(17)
N4 0.028(2) 0.072(4) 0.0212(19) 0.019(2) 0.0129(17) 0.009(2)
N5 0.021(2) 0.032(2) 0.071(3) 0.042(2) 0.015(2) 0.0041(17)
C1 0.0110(17) 0.023(2) 0.0122(16) 0.0025(15) 0.0024(14) 0.0055(15)
C2 0.0123(18) 0.0177(19) 0.0223(19) -0.0051(16) 0.0039(15) 0.0033(15)
C3 0.0110(17) 0.0188(19) 0.0187(18) 0.0033(15) 0.0056(15) 0.0002(15)
C6 0.021(2) 0.042(3) 0.063(4) -0.037(3) 0.010(2) 0.002(2)
C7 0.024(2) 0.010(2) 0.085(4) -0.003(2) 0.014(3) -0.0019(18)
C8 0.020(2) 0.095(5) 0.017(2) -0.027(3) 0.0054(18) 0.004(3)

_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 C1 1.902(4) 7_656 ?
Co1 C1 1.902(4) . ?
Co1 C3 1.906(4) . ?
Co1 C3 1.906(4) 7_656 ?
Co1 C2 1.908(4) 7_656 ?
Co1 C2 1.908(4) . ?
K1 N1 2.878(4) 2_656 ?
K1 N1 2.878(4) . ?
K1 N3 2.887(4) 4_656 ?
K1 N3 2.887(4) 3_455 ?
K1 N2 2.898(4) 3_445 ?
K1 N2 2.898(4) 4_646 ?
N1 C1 1.148(5) . ?
N2 C2 1.152(5) . ?
N2 K1 2.898(4) 3 ?
N3 C3 1.150(5) . ?
N3 K1 2.887(4) 3_545 ?
N4 C6 1.278(8) . ?
N4 C7 1.343(7) . ?
N5 C6 1.296(8) . ?
N5 C8 1.382(8) . ?
C7 C8 1.259(8) . ?

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
C1 Co1 C1 180.000(1) 7_656 . ?
C1 Co1 C3 91.98(16) 7_656 . ?
C1 Co1 C3 88.02(16) . . ?
C1 Co1 C3 88.02(16) 7_656 7_656 ?
C1 Co1 C3 91.98(16) . 7_656 ?
C3 Co1 C3 180.0(2) . 7_656 ?
C1 Co1 C2 88.57(17) 7_656 7_656 ?
C1 Co1 C2 91.43(17) . 7_656 ?
C3 Co1 C2 88.23(17) . 7_656 ?
C3 Co1 C2 91.77(17) 7_656 7_656 ?
C1 Co1 C2 91.43(17) 7_656 . ?
C1 Co1 C2 88.57(17) . . ?
C3 Co1 C2 91.77(17) . . ?
C3 Co1 C2 88.23(17) 7_656 . ?
C2 Co1 C2 180.000(1) 7_656 . ?
N1 K1 N1 170.02(19) 2_656 . ?
N1 K1 N3 83.44(12) 2_656 4_656 ?
N1 K1 N3 103.67(12) . 4_656 ?
N1 K1 N3 103.67(12) 2_656 3_455 ?
N1 K1 N3 83.44(12) . 3_455 ?
N3 K1 N3 90.76(18) 4_656 3_455 ?
N1 K1 N2 89.76(12) 2_656 3_445 ?
N1 K1 N2 82.43(13) . 3_445 ?
N3 K1 N2 171.23(13) 4_656 3_445 ?
N3 K1 N2 96.25(13) 3_455 3_445 ?
N1 K1 N2 82.43(13) 2_656 4_646 ?
N1 K1 N2 89.76(12) . 4_646 ?
N3 K1 N2 96.25(13) 4_656 4_646 ?
N3 K1 N2 171.23(13) 3_455 4_646 ?
N2 K1 N2 77.29(17) 3_445 4_646 ?
C1 N1 K1 169.2(4) . . ?
C2 N2 K1 170.8(4) . 3 ?
C3 N3 K1 170.0(4) . 3_545 ?
C6 N4 C7 109.4(4) . . ?
C6 N5 C8 106.9(4) . . ?
N1 C1 Co1 177.3(4) . . ?
N2 C2 Co1 177.0(4) . . ?
N3 C3 Co1 175.8(4) . . ?
N4 C6 N5 108.3(5) . . ?
C8 C7 N4 107.8(5) . . ?
C7 C8 N5 107.5(4) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.41
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         1.121
_refine_diff_density_min         -0.727
_refine_diff_density_rms         0.117

# start Validation Reply Form

_vrf_PLAT113_a                   
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New Space-group.       P2/m     
RESPONSE: A C-centering structure was suggested by XPREP. 
;

# end Validation Reply Form
# End of cif

