# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © The Royal Society of Chemistry 2014

 

 
 
 
 
 
 
 
 
data_er1320 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety
 '2(C14 H21 Cl Co N5 O5), C4 H10 O'
_chemical_formula_sum 
 'C32 H52 Cl2 Co2 N10 O11' 
_chemical_formula_weight          941.60 
 
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' 
 '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' 
 
_symmetry_cell_setting            monoclinic 
_symmetry_space_group_name_H-M    P2(1)/n
_symmetry_space_group_name_Hall   '-P 2yn'
 
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                    8.0000(1) 
_cell_length_b                    13.5322(2) 
_cell_length_c                    19.2803(3) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  92.183(1) 
_cell_angle_gamma                 90.00 
_cell_volume                      2085.72(5) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     180(2) 
_cell_measurement_reflns_used     15713 
_cell_measurement_theta_min       1.00 
_cell_measurement_theta_max       33.73 
 
_exptl_crystal_description        block 
_exptl_crystal_colour             red 
_exptl_crystal_size_max           0.37 
_exptl_crystal_size_mid           0.18 
_exptl_crystal_size_min           0.10 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.499 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              980 
_exptl_absorpt_coefficient_mu     0.991 
_exptl_absorpt_correction_type 'multi-scan' 
_exptl_absorpt_correction_T_min  0.780
_exptl_absorpt_correction_T_max  0.910
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
 
_exptl_special_details 
; 
 The solvent diethylether is poorly resolved, modelled as one
 1/2 weight molecule disordered about a special position with bond length
 constraints and a common isotropic displacement parameter for the
 C and O atoms. The two -OH hydrogen atoms were placed where they appeared in
 the final difference map (but it's possible the H-bonds are symmetrical).
 JED.
; 
 
_diffrn_ambient_temperature       180(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_measurement_device_type   'Nonius Kappa CCD'
_diffrn_measurement_method        'Thin slice ω and φ scans'
_diffrn_reflns_number             21122 
_diffrn_reflns_av_R_equivalents   0.0426 
_diffrn_reflns_av_sigmaI/netI     0.0580 
_diffrn_reflns_limit_h_min        -12 
_diffrn_reflns_limit_h_max        12 
_diffrn_reflns_limit_k_min        -18 
_diffrn_reflns_limit_k_max        21 
_diffrn_reflns_limit_l_min        -22 
_diffrn_reflns_limit_l_max        30 
_diffrn_reflns_theta_min          3.58 
_diffrn_reflns_theta_max          33.73 
_reflns_number_total              8196 
_reflns_number_gt                 5666 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'Collect (Nonius B.V. 1998)'
_computing_cell_refinement        'HKL Scalepack (Otwinowski & Minor 1997)' 
_computing_data_reduction
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_solution     'SIR-92 (Altomare et al. 1994)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick 1997)' 
_computing_publication_material   'SHELXL-97 (Sheldrick 1997)' 
 
_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)+(0.0623P)²+0.0000P] 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          8196 
_refine_ls_number_parameters      259 
_refine_ls_number_restraints      7 
_refine_ls_R_factor_all           0.0584 
_refine_ls_R_factor_gt            0.0387 
_refine_ls_wR_factor_ref          0.1164 
_refine_ls_wR_factor_gt           0.1130 
_refine_ls_goodness_of_fit_ref    1.030 
_refine_ls_restrained_S_all       1.033 
_refine_ls_shift/su_max           0.004 
_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 0.26172(2) 0.069689(15) 0.171856(10) 0.01770(6) Uani 1 1 d . . . 
Cl1 Cl 0.12995(5) 0.04827(3) 0.068932(19) 0.02714(9) Uani 1 1 d . . . 
C1 C 0.38655(19) 0.00941(12) 0.30947(8) 0.0237(3) Uani 1 1 d . . . 
H1 H 0.3580 -0.0552 0.2938 0.028 Uiso 1 1 calc R . . 
O1 O 0.53163(17) 0.12487(10) 0.46854(6) 0.0366(3) Uani 1 1 d . . . 
O2 O 0.36849(15) -0.13224(9) 0.16463(6) 0.0308(3) Uani 1 1 d . . . 
H2X H 0.2778 -0.1347 0.1851 0.046 Uiso 1 1 calc R . . 
O3 O 0.42861(14) 0.24015(9) 0.11913(6) 0.0292(3) Uani 1 1 d . . . 
H3X H 0.3433 0.2632 0.1374 0.044 Uiso 1 1 calc R . . 
O4 O 0.15350(13) 0.26972(8) 0.17119(6) 0.0241(2) Uani 1 1 d . . . 
O5 O 0.09436(15) -0.10005(9) 0.21845(6) 0.0294(3) Uani 1 1 d . . . 
N1 N 0.36950(15) 0.08551(9) 0.26437(6) 0.0183(2) Uani 1 1 d . . . 
N2 N 0.40525(16) -0.03719(10) 0.15014(6) 0.0226(3) Uani 1 1 d . . . 
N3 N 0.43377(15) 0.14153(10) 0.12846(6) 0.0212(3) Uani 1 1 d . . . 
N4 N 0.11822(15) 0.17734(10) 0.18980(6) 0.0201(2) Uani 1 1 d . . . 
N5 N 0.08877(16) -0.00222(10) 0.21232(7) 0.0220(3) Uani 1 1 d . . . 
C2 C 0.4435(2) 0.02180(13) 0.37707(8) 0.0273(3) Uani 1 1 d . . . 
H2 H 0.4545 -0.0335 0.4072 0.033 Uiso 1 1 calc R . . 
C3 C 0.48518(19) 0.11635(13) 0.40112(8) 0.0253(3) Uani 1 1 d . . . 
C4 C 0.47445(19) 0.19439(12) 0.35428(8) 0.0234(3) Uani 1 1 d . . . 
H4 H 0.5061 0.2593 0.3681 0.028 Uiso 1 1 calc R . . 
C5 C 0.41658(18) 0.17537(12) 0.28707(8) 0.0214(3) Uani 1 1 d . . . 
H5 H 0.4098 0.2289 0.2552 0.026 Uiso 1 1 calc R . . 
C6 C 0.5385(2) -0.01573(13) 0.11739(8) 0.0254(3) Uani 1 1 d . . . 
C7 C 0.55502(19) 0.09059(13) 0.10396(8) 0.0249(3) Uani 1 1 d . . . 
C8 C 0.6617(2) -0.09025(15) 0.09365(10) 0.0372(4) Uani 1 1 d . . . 
H8A H 0.6345 -0.1553 0.1126 0.056 Uiso 1 1 calc R . . 
H8B H 0.7746 -0.0711 0.1100 0.056 Uiso 1 1 calc R . . 
H8C H 0.6569 -0.0933 0.0428 0.056 Uiso 1 1 calc R . . 
C9 C 0.6931(2) 0.13325(15) 0.06294(9) 0.0350(4) Uani 1 1 d . . . 
H9A H 0.6771 0.2048 0.0582 0.052 Uiso 1 1 calc R . . 
H9B H 0.6916 0.1028 0.0168 0.052 Uiso 1 1 calc R . . 
H9C H 0.8009 0.1201 0.0870 0.052 Uiso 1 1 calc R . . 
C10 C -0.03551(19) 0.05017(13) 0.23481(8) 0.0245(3) Uani 1 1 d . . . 
C11 C -0.01902(18) 0.15544(12) 0.22047(8) 0.0232(3) Uani 1 1 d . . . 
C12 C -0.1793(2) 0.00465(15) 0.27027(10) 0.0376(4) Uani 1 1 d . . . 
H12A H -0.1487 -0.0621 0.2859 0.056 Uiso 1 1 calc R . . 
H12B H -0.2764 0.0010 0.2378 0.056 Uiso 1 1 calc R . . 
H12C H -0.2072 0.0451 0.3104 0.056 Uiso 1 1 calc R . . 
C13 C -0.1470(2) 0.23165(15) 0.23687(10) 0.0349(4) Uani 1 1 d . . . 
H13A H -0.0980 0.2977 0.2329 0.052 Uiso 1 1 calc R . . 
H13B H -0.1837 0.2216 0.2843 0.052 Uiso 1 1 calc R . . 
H13C H -0.2432 0.2256 0.2041 0.052 Uiso 1 1 calc R . . 
C14 C 0.5666(3) 0.22212(15) 0.49497(9) 0.0413(5) Uani 1 1 d . . . 
H14A H 0.5742 0.2201 0.5458 0.062 Uiso 1 1 calc R . . 
H14B H 0.4766 0.2672 0.4798 0.062 Uiso 1 1 calc R . . 
H14C H 0.6729 0.2455 0.4774 0.062 Uiso 1 1 calc R . . 
C51 C 0.5402(16) -0.6419(8) -0.0560(5) 0.1123(12) Uiso 0.50 1 d PD A -1 
H51A H 0.5423 -0.6585 -0.1054 0.168 Uiso 0.50 1 calc PR A -1 
H51B H 0.4588 -0.6842 -0.0335 0.168 Uiso 0.50 1 calc PR A -1 
H51C H 0.6515 -0.6526 -0.0342 0.168 Uiso 0.50 1 calc PR A -1 
C52 C 0.4964(12) -0.5471(7) -0.0488(4) 0.1123(12) Uiso 0.50 1 d PD A -1 
H52A H 0.3755 -0.5416 -0.0611 0.135 Uiso 0.50 1 calc PR A -1 
H52B H 0.5567 -0.5082 -0.0834 0.135 Uiso 0.50 1 calc PR A -1 
O53 O 0.5254(8) -0.5011(5) 0.0175(3) 0.1123(12) Uiso 0.50 1 d PD A -1 
C54 C 0.4309(11) -0.4038(6) 0.0122(4) 0.1123(12) Uiso 0.50 1 d PD A -1 
H54A H 0.4724 -0.3628 -0.0260 0.135 Uiso 0.50 1 calc PR A -1 
H54B H 0.3096 -0.4153 0.0040 0.135 Uiso 0.50 1 calc PR A -1 
C55 C 0.4652(15) -0.3550(8) 0.0808(4) 0.1123(12) Uiso 0.50 1 d PD A -1 
H55A H 0.4147 -0.2890 0.0804 0.168 Uiso 0.50 1 calc PR A -1 
H55B H 0.5863 -0.3493 0.0895 0.168 Uiso 0.50 1 calc PR A -1 
H55C H 0.4169 -0.3948 0.1176 0.168 Uiso 0.50 1 calc PR A -1 
 
 
_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 N5 1.8847(13) . ? 
Co1 N4 1.8948(12) . ? 
Co1 N2 1.9032(13) . ? 
Co1 N3 1.9046(13) . ? 
Co1 N1 1.9630(12) . ? 
Co1 Cl1 2.2302(4) . ? 
C1 N1 1.3514(19) . ? 
C1 C2 1.375(2) . ? 
C1 H1 0.9500 . ? 
O1 C3 1.3433(19) . ? 
O1 C14 1.435(2) . ? 
O2 N2 1.3510(18) . ? 
O2 H2X 0.8400 . ? 
O3 N3 1.3470(17) . ? 
O3 H3X 0.8400 . ? 
O4 N4 1.3338(16) . ? 
O5 N5 1.3297(18) . ? 
N1 C5 1.3415(19) . ? 
N2 C6 1.292(2) . ? 
N3 C7 1.294(2) . ? 
N4 C11 1.3009(19) . ? 
N5 C10 1.308(2) . ? 
C2 C3 1.397(2) . ? 
C2 H2 0.9500 . ? 
C3 C4 1.390(2) . ? 
C4 C5 1.383(2) . ? 
C4 H4 0.9500 . ? 
C5 H5 0.9500 . ? 
C6 C7 1.469(2) . ? 
C6 C8 1.494(2) . ? 
C7 C9 1.499(2) . ? 
C8 H8A 0.9800 . ? 
C8 H8B 0.9800 . ? 
C8 H8C 0.9800 . ? 
C9 H9A 0.9800 . ? 
C9 H9B 0.9800 . ? 
C9 H9C 0.9800 . ? 
C10 C11 1.458(2) . ? 
C10 C12 1.493(2) . ? 
C11 C13 1.496(2) . ? 
C12 H12A 0.9800 . ? 
C12 H12B 0.9800 . ? 
C12 H12C 0.9800 . ? 
C13 H13A 0.9800 . ? 
C13 H13B 0.9800 . ? 
C13 H13C 0.9800 . ? 
C14 H14A 0.9800 . ? 
C14 H14B 0.9800 . ? 
C14 H14C 0.9800 . ? 
C51 C52 1.338(11) . ? 
C51 H51A 0.9800 . ? 
C51 H51B 0.9800 . ? 
C51 H51C 0.9800 . ? 
C52 O53 1.433(9) . ? 
C52 H52A 0.9900 . ? 
C52 H52B 0.9900 . ? 
O53 C54 1.520(10) . ? 
C54 C55 1.495(10) . ? 
C54 H54A 0.9900 . ? 
C54 H54B 0.9900 . ? 
C55 H55A 0.9800 . ? 
C55 H55B 0.9800 . ? 
C55 H55C 0.9800 . ? 
 
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 
N5 Co1 N4 82.06(6) . . ? 
N5 Co1 N2 99.05(6) . . ? 
N4 Co1 N2 177.80(5) . . ? 
N5 Co1 N3 178.39(5) . . ? 
N4 Co1 N3 98.10(6) . . ? 
N2 Co1 N3 80.74(6) . . ? 
N5 Co1 N1 89.09(5) . . ? 
N4 Co1 N1 89.91(5) . . ? 
N2 Co1 N1 92.00(5) . . ? 
N3 Co1 N1 92.51(5) . . ? 
N5 Co1 Cl1 88.37(4) . . ? 
N4 Co1 Cl1 89.61(4) . . ? 
N2 Co1 Cl1 88.52(4) . . ? 
N3 Co1 Cl1 90.02(4) . . ? 
N1 Co1 Cl1 177.46(4) . . ? 
N1 C1 C2 122.61(15) . . ? 
N1 C1 H1 118.7 . . ? 
C2 C1 H1 118.7 . . ? 
C3 O1 C14 117.74(14) . . ? 
N2 O2 H2X 109.5 . . ? 
N3 O3 H3X 109.5 . . ? 
C5 N1 C1 117.43(13) . . ? 
C5 N1 Co1 120.23(10) . . ? 
C1 N1 Co1 122.12(11) . . ? 
C6 N2 O2 120.34(14) . . ? 
C6 N2 Co1 116.90(12) . . ? 
O2 N2 Co1 122.69(9) . . ? 
C7 N3 O3 119.91(13) . . ? 
C7 N3 Co1 116.92(12) . . ? 
O3 N3 Co1 123.05(9) . . ? 
C11 N4 O4 121.79(13) . . ? 
C11 N4 Co1 115.82(11) . . ? 
O4 N4 Co1 122.38(9) . . ? 
C10 N5 O5 122.23(13) . . ? 
C10 N5 Co1 115.88(12) . . ? 
O5 N5 Co1 121.88(10) . . ? 
C1 C2 C3 119.52(15) . . ? 
C1 C2 H2 120.2 . . ? 
C3 C2 H2 120.2 . . ? 
O1 C3 C4 124.85(15) . . ? 
O1 C3 C2 116.97(15) . . ? 
C4 C3 C2 118.17(14) . . ? 
C5 C4 C3 118.52(15) . . ? 
C5 C4 H4 120.7 . . ? 
C3 C4 H4 120.7 . . ? 
N1 C5 C4 123.64(14) . . ? 
N1 C5 H5 118.2 . . ? 
C4 C5 H5 118.2 . . ? 
N2 C6 C7 112.82(14) . . ? 
N2 C6 C8 124.34(17) . . ? 
C7 C6 C8 122.83(15) . . ? 
N3 C7 C6 112.56(14) . . ? 
N3 C7 C9 124.42(16) . . ? 
C6 C7 C9 122.93(15) . . ? 
C6 C8 H8A 109.5 . . ? 
C6 C8 H8B 109.5 . . ? 
H8A C8 H8B 109.5 . . ? 
C6 C8 H8C 109.5 . . ? 
H8A C8 H8C 109.5 . . ? 
H8B C8 H8C 109.5 . . ? 
C7 C9 H9A 109.5 . . ? 
C7 C9 H9B 109.5 . . ? 
H9A C9 H9B 109.5 . . ? 
C7 C9 H9C 109.5 . . ? 
H9A C9 H9C 109.5 . . ? 
H9B C9 H9C 109.5 . . ? 
N5 C10 C11 113.03(14) . . ? 
N5 C10 C12 122.45(16) . . ? 
C11 C10 C12 124.51(15) . . ? 
N4 C11 C10 113.13(14) . . ? 
N4 C11 C13 122.37(16) . . ? 
C10 C11 C13 124.47(14) . . ? 
C10 C12 H12A 109.5 . . ? 
C10 C12 H12B 109.5 . . ? 
H12A C12 H12B 109.5 . . ? 
C10 C12 H12C 109.5 . . ? 
H12A C12 H12C 109.5 . . ? 
H12B C12 H12C 109.5 . . ? 
C11 C13 H13A 109.5 . . ? 
C11 C13 H13B 109.5 . . ? 
H13A C13 H13B 109.5 . . ? 
C11 C13 H13C 109.5 . . ? 
H13A C13 H13C 109.5 . . ? 
H13B C13 H13C 109.5 . . ? 
O1 C14 H14A 109.5 . . ? 
O1 C14 H14B 109.5 . . ? 
H14A C14 H14B 109.5 . . ? 
O1 C14 H14C 109.5 . . ? 
H14A C14 H14C 109.5 . . ? 
H14B C14 H14C 109.5 . . ? 
C51 C52 O53 118.3(8) . . ? 
C51 C52 H52A 107.7 . . ? 
O53 C52 H52A 107.7 . . ? 
C51 C52 H52B 107.7 . . ? 
O53 C52 H52B 107.7 . . ? 
H52A C52 H52B 107.1 . . ? 
C52 O53 C54 104.7(5) . . ? 
C55 C54 O53 104.4(7) . . ? 
C55 C54 H54A 110.9 . . ? 
O53 C54 H54A 110.9 . . ? 
C55 C54 H54B 110.9 . . ? 
O53 C54 H54B 110.9 . . ? 
H54A C54 H54B 108.9 . . ? 
 
_diffrn_measured_fraction_theta_max    0.983 
_diffrn_reflns_theta_full              33.73 
_diffrn_measured_fraction_theta_full   0.983 
_refine_diff_density_max    0.862 
_refine_diff_density_min   -0.966 
_refine_diff_density_rms    0.076 
