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


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#                 Cambridge Crystallographic Data Centre
#                                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. 
# 
#  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 
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#  data retrieval see:
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data_cmap027a
_database_code_depnum_ccdc_archive 'CCDC 883590'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H15 Cl2 Co N4 O'
_chemical_formula_weight         361.11
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'
Cl Cl 0.1484 0.1585 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a                   8.5370(10)
_cell_length_b                   8.9420(10)
_cell_length_c                   10.680(2)
_cell_angle_alpha                70.914(6)
_cell_angle_beta                 75.052(6)
_cell_angle_gamma                75.559(7)
_cell_volume                     732.14(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    11267
_cell_measurement_theta_min      1.0
_cell_measurement_theta_max      27.48
_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_absorpt_coefficient_mu    1.536
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8615
_exptl_absorpt_correction_T_max  0.9554
_exptl_absorpt_process_details   scalepack
_exptl_special_details           
;
?
;
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_detector_area_resol_mean 9
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_method       CCD
_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_reflns_number            4893
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_sigmaI/netI    0.0787
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.12
_diffrn_reflns_theta_max         26.37
_reflns_number_total             2970
_reflns_number_gt                2046
_reflns_threshold_expression     >2\s(I)
_computing_data_collection       'KappaCCD Server Software (Nonius, 1997)'
_computing_structure_solution    'Shelxs-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997) and Mercury (CCDC)'
_computing_publication_material  'shelxl-97 (Sheldrick, 1997)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_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^ > 2\s(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^)+(0.0535P)^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    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2970
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1187
_refine_ls_wR_factor_gt          0.1046
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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 0.44341(6) 0.15667(6) 0.41013(6) 0.03041(18) Uani 1 1 d . . .
Cl1 Cl 0.44539(11) 0.28717(11) 0.55902(11) 0.0376(3) Uani 1 1 d . . .
N2 N 0.4426(4) 0.0609(4) 0.2708(4) 0.0369(8) Uani 1 1 d . . .
H2A H 0.4552 -0.0480 0.3054 0.044 Uiso 1 1 calc R . .
H2B H 0.3439 0.0970 0.2435 0.044 Uiso 1 1 calc R . .
N1 N 0.5484(4) 0.3148(4) 0.2529(4) 0.0341(8) Uani 1 1 d . . .
N3 N 0.2119(4) 0.2558(4) 0.4139(4) 0.0334(7) Uani 1 1 d . . .
N4 N 0.3584(4) -0.0110(4) 0.5515(3) 0.0310(7) Uani 1 1 d . . .
C6 C 0.1440(5) 0.3973(5) 0.3406(5) 0.0384(10) Uani 1 1 d . . .
H6 H 0.2128 0.4628 0.2733 0.046 Uiso 1 1 calc R . .
C5 C -0.0247(5) 0.4510(5) 0.3604(5) 0.0451(11) Uani 1 1 d . . .
H5 H -0.0698 0.5509 0.3066 0.054 Uiso 1 1 calc R . .
C1 C 0.2035(5) 0.0104(5) 0.5878(4) 0.0334(9) Uani 1 1 d . . .
H1 H 0.1499 -0.0661 0.6581 0.040 Uiso 1 1 calc R . .
C8 C 0.6651(6) 0.5511(6) 0.1388(5) 0.0533(12) Uani 1 1 d . . .
H8 H 0.6800 0.6516 0.1392 0.064 Uiso 1 1 calc R . .
C2 C 0.1112(5) 0.1626(5) 0.5134(4) 0.0337(9) Uani 1 1 d . . .
C4 C -0.1253(5) 0.3567(5) 0.4595(5) 0.0455(11) Uani 1 1 d . . .
H4 H -0.2402 0.3912 0.4738 0.055 Uiso 1 1 calc R . .
C10 C 0.7060(6) 0.3498(6) 0.0294(5) 0.0515(12) Uani 1 1 d . . .
H10 H 0.7503 0.3105 -0.0464 0.062 Uiso 1 1 calc R . .
C7 C 0.5728(5) 0.4601(5) 0.2482(5) 0.0429(10) Uani 1 1 d . . .
H7 H 0.5244 0.5004 0.3231 0.052 Uiso 1 1 calc R . .
C9 C 0.7353(6) 0.4946(7) 0.0293(5) 0.0597(14) Uani 1 1 d . . .
H9 H 0.8027 0.5536 -0.0452 0.072 Uiso 1 1 calc R . .
C12 C 0.5768(6) 0.1019(5) 0.1535(5) 0.0457(11) Uani 1 1 d . . .
H12A H 0.5444 0.1053 0.0709 0.055 Uiso 1 1 calc R . .
H12B H 0.6764 0.0199 0.1653 0.055 Uiso 1 1 calc R . .
C11 C 0.6109(5) 0.2632(5) 0.1419(4) 0.0399(10) Uani 1 1 d . . .
Cl2 Cl -0.13733(17) -0.11303(19) 0.86519(15) 0.0718(4) Uani 1 1 d . . .
C3 C -0.0569(5) 0.2106(5) 0.5383(5) 0.0407(10) Uani 1 1 d . . .
H3 H -0.1241 0.1454 0.6077 0.049 Uiso 1 1 calc R . .
O1 O 0.0448(5) 0.1724(5) 0.8465(4) 0.0777(12) Uani 1 1 d . . .
H1O H 0.0571 0.1477 0.9364 0.070 Uiso 1 1 d . . .
H2O H -0.0181 0.0907 0.8491 0.070 Uiso 1 1 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 0.0266(3) 0.0261(3) 0.0393(3) -0.0090(2) -0.0103(2) -0.00228(19)
Cl1 0.0388(5) 0.0309(5) 0.0461(7) -0.0140(5) -0.0119(5) -0.0039(4)
N2 0.0376(18) 0.0336(18) 0.041(2) -0.0085(16) -0.0155(16) -0.0033(15)
N1 0.0324(17) 0.0302(17) 0.040(2) -0.0072(15) -0.0115(15) -0.0047(13)
N3 0.0326(17) 0.0303(17) 0.040(2) -0.0115(15) -0.0134(15) -0.0009(14)
N4 0.0313(17) 0.0296(16) 0.035(2) -0.0131(15) -0.0079(14) -0.0043(13)
C6 0.038(2) 0.032(2) 0.044(3) -0.0059(19) -0.0156(19) -0.0016(17)
C5 0.043(2) 0.038(2) 0.053(3) -0.011(2) -0.020(2) 0.0046(19)
C1 0.033(2) 0.030(2) 0.042(2) -0.0096(18) -0.0143(18) -0.0062(16)
C8 0.060(3) 0.048(3) 0.054(3) -0.005(2) -0.013(2) -0.025(2)
C2 0.0300(19) 0.034(2) 0.042(3) -0.0136(19) -0.0130(18) -0.0030(16)
C4 0.031(2) 0.046(3) 0.064(3) -0.018(2) -0.020(2) 0.0007(19)
C10 0.054(3) 0.059(3) 0.034(3) -0.009(2) -0.004(2) -0.007(2)
C7 0.049(2) 0.035(2) 0.048(3) -0.009(2) -0.014(2) -0.0112(19)
C9 0.060(3) 0.069(3) 0.047(3) -0.001(3) -0.005(2) -0.031(3)
C12 0.050(3) 0.050(3) 0.038(3) -0.017(2) -0.009(2) -0.004(2)
C11 0.034(2) 0.039(2) 0.040(3) -0.006(2) -0.0081(19) -0.0024(18)
Cl2 0.0679(8) 0.0877(10) 0.0660(9) 0.0003(8) -0.0309(7) -0.0359(8)
C3 0.030(2) 0.040(2) 0.055(3) -0.016(2) -0.0095(19) -0.0063(18)
O1 0.103(3) 0.066(2) 0.062(3) -0.009(2) -0.018(2) -0.023(2)
_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
Co1 N4 1.884(3) . ?
Co1 N4 1.907(3) 2_656 ?
Co1 N2 1.947(3) . ?
Co1 N3 1.950(3) . ?
Co1 N1 1.981(3) . ?
Co1 Cl1 2.2645(11) . ?
Co1 Co1 2.9255(11) 2_656 ?
N2 C12 1.478(5) . ?
N1 C11 1.345(5) . ?
N1 C7 1.350(5) . ?
N3 C6 1.331(5) . ?
N3 C2 1.367(5) . ?
N4 C1 1.263(5) . ?
N4 Co1 1.907(3) 2_656 ?
C6 C5 1.383(6) . ?
C5 C4 1.370(6) . ?
C1 C2 1.479(6) . ?
C8 C9 1.362(7) . ?
C8 C7 1.368(6) . ?
C2 C3 1.372(5) . ?
C4 C3 1.382(6) . ?
C10 C9 1.378(7) . ?
C10 C11 1.380(6) . ?
C12 C11 1.501(6) . ?
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
N4 Co1 N4 79.00(14) . 2_656 ?
N4 Co1 N2 93.40(13) . . ?
N4 Co1 N2 89.93(13) 2_656 . ?
N4 Co1 N3 83.98(14) . . ?
N4 Co1 N3 162.98(14) 2_656 . ?
N2 Co1 N3 91.04(14) . . ?
N4 Co1 N1 173.84(13) . . ?
N4 Co1 N1 96.72(13) 2_656 . ?
N2 Co1 N1 82.10(14) . . ?
N3 Co1 N1 100.25(14) . . ?
N4 Co1 Cl1 90.97(10) . . ?
N4 Co1 Cl1 92.37(10) 2_656 . ?
N2 Co1 Cl1 175.38(10) . . ?
N3 Co1 Cl1 87.93(10) . . ?
N1 Co1 Cl1 93.64(10) . . ?
N4 Co1 Co1 39.78(10) . 2_656 ?
N4 Co1 Co1 39.22(9) 2_656 2_656 ?
N2 Co1 Co1 92.15(10) . 2_656 ?
N3 Co1 Co1 123.76(10) . 2_656 ?
N1 Co1 Co1 135.78(10) . 2_656 ?
Cl1 Co1 Co1 92.17(4) . 2_656 ?
C12 N2 Co1 111.0(2) . . ?
C11 N1 C7 117.8(4) . . ?
C11 N1 Co1 114.4(3) . . ?
C7 N1 Co1 127.6(3) . . ?
C6 N3 C2 118.6(3) . . ?
C6 N3 Co1 130.0(3) . . ?
C2 N3 Co1 111.4(3) . . ?
C1 N4 Co1 115.8(3) . . ?
C1 N4 Co1 143.2(3) . 2_656 ?
Co1 N4 Co1 101.00(14) . 2_656 ?
N3 C6 C5 122.0(4) . . ?
C4 C5 C6 119.2(4) . . ?
N4 C1 C2 116.2(4) . . ?
C9 C8 C7 119.4(4) . . ?
N3 C2 C3 121.8(4) . . ?
N3 C2 C1 112.7(3) . . ?
C3 C2 C1 125.5(4) . . ?
C5 C4 C3 119.6(4) . . ?
C9 C10 C11 119.3(4) . . ?
N1 C7 C8 122.6(4) . . ?
C8 C9 C10 119.1(4) . . ?
N2 C12 C11 108.9(3) . . ?
N1 C11 C10 121.8(4) . . ?
N1 C11 C12 114.9(4) . . ?
C10 C11 C12 123.2(4) . . ?
C2 C3 C4 118.7(4) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 Co1 N2 C12 -149.3(3) . . . . ?
N4 Co1 N2 C12 -70.3(3) 2_656 . . . ?
N3 Co1 N2 C12 126.7(3) . . . . ?
N1 Co1 N2 C12 26.4(3) . . . . ?
Cl1 Co1 N2 C12 49.5(14) . . . . ?
Co1 Co1 N2 C12 -109.5(3) 2_656 . . . ?
N4 Co1 N1 C11 25.3(14) . . . . ?
N4 Co1 N1 C11 70.9(3) 2_656 . . . ?
N2 Co1 N1 C11 -18.1(3) . . . . ?
N3 Co1 N1 C11 -107.7(3) . . . . ?
Cl1 Co1 N1 C11 163.8(3) . . . . ?
Co1 Co1 N1 C11 66.9(3) 2_656 . . . ?
N4 Co1 N1 C7 -150.0(12) . . . . ?
N4 Co1 N1 C7 -104.3(3) 2_656 . . . ?
N2 Co1 N1 C7 166.7(4) . . . . ?
N3 Co1 N1 C7 77.0(4) . . . . ?
Cl1 Co1 N1 C7 -11.5(3) . . . . ?
Co1 Co1 N1 C7 -108.4(3) 2_656 . . . ?
N4 Co1 N3 C6 178.5(4) . . . . ?
N4 Co1 N3 C6 178.7(4) 2_656 . . . ?
N2 Co1 N3 C6 -88.1(4) . . . . ?
N1 Co1 N3 C6 -6.0(4) . . . . ?
Cl1 Co1 N3 C6 87.3(4) . . . . ?
Co1 Co1 N3 C6 178.6(3) 2_656 . . . ?
N4 Co1 N3 C2 1.8(3) . . . . ?
N4 Co1 N3 C2 2.0(6) 2_656 . . . ?
N2 Co1 N3 C2 95.2(3) . . . . ?
N1 Co1 N3 C2 177.3(2) . . . . ?
Cl1 Co1 N3 C2 -89.4(2) . . . . ?
Co1 Co1 N3 C2 1.9(3) 2_656 . . . ?
N4 Co1 N4 C1 178.7(4) 2_656 . . . ?
N2 Co1 N4 C1 -92.1(3) . . . . ?
N3 Co1 N4 C1 -1.4(3) . . . . ?
N1 Co1 N4 C1 -135.0(12) . . . . ?
Cl1 Co1 N4 C1 86.4(3) . . . . ?
Co1 Co1 N4 C1 178.7(4) 2_656 . . . ?
N4 Co1 N4 Co1 0.0 2_656 . . 2_656 ?
N2 Co1 N4 Co1 89.27(15) . . . 2_656 ?
N3 Co1 N4 Co1 179.96(16) . . . 2_656 ?
N1 Co1 N4 Co1 46.4(13) . . . 2_656 ?
Cl1 Co1 N4 Co1 -92.22(11) . . . 2_656 ?
C2 N3 C6 C5 -1.3(6) . . . . ?
Co1 N3 C6 C5 -177.8(3) . . . . ?
N3 C6 C5 C4 0.8(7) . . . . ?
Co1 N4 C1 C2 0.6(4) . . . . ?
Co1 N4 C1 C2 178.4(3) 2_656 . . . ?
C6 N3 C2 C3 0.6(6) . . . . ?
Co1 N3 C2 C3 177.7(3) . . . . ?
C6 N3 C2 C1 -179.1(4) . . . . ?
Co1 N3 C2 C1 -1.9(4) . . . . ?
N4 C1 C2 N3 0.9(5) . . . . ?
N4 C1 C2 C3 -178.7(4) . . . . ?
C6 C5 C4 C3 0.4(7) . . . . ?
C11 N1 C7 C8 -3.6(6) . . . . ?
Co1 N1 C7 C8 171.5(4) . . . . ?
C9 C8 C7 N1 0.3(7) . . . . ?
C7 C8 C9 C10 2.6(8) . . . . ?
C11 C10 C9 C8 -2.1(8) . . . . ?
Co1 N2 C12 C11 -29.9(4) . . . . ?
C7 N1 C11 C10 4.0(6) . . . . ?
Co1 N1 C11 C10 -171.7(4) . . . . ?
C7 N1 C11 C12 -179.0(4) . . . . ?
Co1 N1 C11 C12 5.2(5) . . . . ?
C9 C10 C11 N1 -1.3(7) . . . . ?
C9 C10 C11 C12 -177.9(5) . . . . ?
N2 C12 C11 N1 16.0(5) . . . . ?
N2 C12 C11 C10 -167.1(4) . . . . ?
N3 C2 C3 C4 0.6(6) . . . . ?
C1 C2 C3 C4 -179.8(4) . . . . ?
C5 C4 C3 C2 -1.0(7) . . . . ?
_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.937
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.088