# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1403895'
_audit_update_record             
;
2015-05-29 deposited with the CCDC.
2016-10-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H28 Co N2 O6'
_chemical_formula_sum            'C28 H28 Co N2 O6'
_chemical_formula_weight         547.45

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           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2460(12)
_cell_length_b                   9.5510(19)
_cell_length_c                   11.301(2)
_cell_angle_alpha                97.11(3)
_cell_angle_beta                 96.87(3)
_cell_angle_gamma                106.95(3)
_cell_volume                     631.3(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4836
_cell_measurement_theta_min      1.84
_cell_measurement_theta_max      25.00

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             285
_exptl_absorpt_coefficient_mu    0.726
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Mar345 dtb'
_diffrn_measurement_method       'image-plate detector - phi oscillation'
_diffrn_detector_area_resol_mean 0.71
_diffrn_standards_number         .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        .
_diffrn_reflns_number            4836
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_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         1.84
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2098
_reflns_number_gt                1889
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'MAR345 dtb Program Manual(1.24-4, 2013)'
_computing_cell_refinement       'Automar software package (1.24-4, 2013)'
_computing_data_reduction        'Automar software package (1.24-4, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'PLATON (Spek, 2000)'

_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)+(0.0318P)²+0.5935P] where P=(Fo²+2Fc²)/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         2098
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1015
_refine_ls_wR_factor_gt          0.0977
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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 0.5000 0.5000 0.5000 0.0462(2) Uani 1 2 d S . .
O2 O 0.7474(3) 0.5978(2) 0.41371(18) 0.0523(5) Uani 1 1 d . . .
O1 O 0.4632(3) 0.7178(2) 0.5596(2) 0.0578(6) Uani 1 1 d . . .
O3 O 0.2760(3) 0.4757(2) 0.34401(19) 0.0545(5) Uani 1 1 d . . .
N1 N 0.2585(4) 0.8627(3) 0.6254(2) 0.0510(6) Uani 1 1 d . . .
C1 C 0.2831(5) 0.7336(3) 0.5817(3) 0.0488(7) Uani 1 1 d . . .
H1 H 0.145(6) 0.652(4) 0.569(3) 0.073 Uiso 1 1 d . . .
C5 C 0.5322(5) 0.6160(3) 0.2270(3) 0.0456(6) Uani 1 1 d . . .
C6 C 0.3198(5) 0.5289(3) 0.2509(3) 0.0529(7) Uani 1 1 d . . .
H6 H 0.179(6) 0.510(4) 0.182(3) 0.079 Uiso 1 1 d . . .
C4 C 0.7367(5) 0.6438(3) 0.3109(3) 0.0458(7) Uani 1 1 d . . .
C7 C 0.5444(5) 0.6717(3) 0.1120(3) 0.0495(7) Uani 1 1 d . . .
C8 C 0.7568(6) 0.7513(3) 0.0857(3) 0.0535(7) Uani 1 1 d . . .
C2 C 0.4477(6) 0.9990(4) 0.6533(4) 0.0746(10) Uani 1 1 d . . .
H2A H 0.5829 0.9786 0.6350 0.112 Uiso 1 1 calc R . .
H2B H 0.4687 1.0390 0.7376 0.112 Uiso 1 1 calc R . .
H2C H 0.4167 1.0696 0.6058 0.112 Uiso 1 1 calc R . .
C9 C 0.9561(5) 0.7774(4) 0.1716(3) 0.0571(8) Uani 1 1 d . . .
H9 H 1.0957 0.8304 0.1541 0.068 Uiso 1 1 calc R . .
C11 C 0.7740(7) 0.8031(4) -0.0260(3) 0.0687(9) Uani 1 1 d . . .
H11 H 0.9156 0.8541 -0.0425 0.082 Uiso 1 1 calc R . .
C10 C 0.9474(5) 0.7269(3) 0.2784(3) 0.0537(7) Uani 1 1 d . . .
H10 H 1.0814 0.7465 0.3324 0.064 Uiso 1 1 calc R . .
C12 C 0.5845(7) 0.7788(5) -0.1097(3) 0.0783(11) Uani 1 1 d . . .
H12 H 0.5966 0.8129 -0.1830 0.094 Uiso 1 1 calc R . .
C14 C 0.3523(6) 0.6504(4) 0.0237(3) 0.0622(9) Uani 1 1 d . . .
H14 H 0.2090 0.6001 0.0385 0.075 Uiso 1 1 calc R . .
C3 C 0.0393(6) 0.8730(4) 0.6497(4) 0.0783(11) Uani 1 1 d . . .
H3A H -0.0742 0.7781 0.6232 0.118 Uiso 1 1 calc R . .
H3B H -0.0001 0.9452 0.6069 0.118 Uiso 1 1 calc R . .
H3C H 0.0477 0.9026 0.7349 0.118 Uiso 1 1 calc R . .
C13 C 0.3740(7) 0.7030(4) -0.0844(3) 0.0749(10) Uani 1 1 d . . .
H13 H 0.2450 0.6872 -0.1411 0.090 Uiso 1 1 calc R . .


_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 O2 1.989(2) 2_666 ?
Co1 O2 1.989(2) . ?
Co1 O3 2.059(2) 2_666 ?
Co1 O3 2.059(2) . ?
Co1 O1 2.191(2) 2_666 ?
Co1 O1 2.191(2) . ?
O2 C4 1.293(3) . ?
O1 C1 1.228(3) . ?
O3 C6 1.250(4) . ?
N1 C1 1.329(4) . ?
N1 C2 1.450(4) . ?
N1 C3 1.457(4) . ?
C1 H1 0.96(4) . ?
C5 C6 1.422(4) . ?
C5 C4 1.431(4) . ?
C5 C7 1.466(4) . ?
C6 H6 1.06(4) . ?
C4 C10 1.441(4) . ?
C7 C8 1.410(4) . ?
C7 C14 1.413(4) . ?
C8 C11 1.416(4) . ?
C8 C9 1.423(5) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C9 C10 1.356(4) . ?
C9 H9 0.9300 . ?
C11 C12 1.367(5) . ?
C11 H11 0.9300 . ?
C10 H10 0.9300 . ?
C12 C13 1.386(5) . ?
C12 H12 0.9300 . ?
C14 C13 1.384(5) . ?
C14 H14 0.9300 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C13 H13 0.9300 . ?

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
O2 Co1 O2 180.0 2_666 . ?
O2 Co1 O3 87.71(8) 2_666 2_666 ?
O2 Co1 O3 92.29(8) . 2_666 ?
O2 Co1 O3 92.29(8) 2_666 . ?
O2 Co1 O3 87.71(8) . . ?
O3 Co1 O3 180.0 2_666 . ?
O2 Co1 O1 88.97(9) 2_666 2_666 ?
O2 Co1 O1 91.03(9) . 2_666 ?
O3 Co1 O1 89.71(9) 2_666 2_666 ?
O3 Co1 O1 90.29(9) . 2_666 ?
O2 Co1 O1 91.03(9) 2_666 . ?
O2 Co1 O1 88.97(9) . . ?
O3 Co1 O1 90.29(9) 2_666 . ?
O3 Co1 O1 89.71(9) . . ?
O1 Co1 O1 180.000(1) 2_666 . ?
C4 O2 Co1 130.02(19) . . ?
C1 O1 Co1 122.70(19) . . ?
C6 O3 Co1 126.8(2) . . ?
C1 N1 C2 122.0(3) . . ?
C1 N1 C3 121.2(3) . . ?
C2 N1 C3 116.8(3) . . ?
O1 C1 N1 124.2(3) . . ?
O1 C1 H1 122(2) . . ?
N1 C1 H1 113(2) . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 C7 119.6(3) . . ?
C4 C5 C7 119.3(3) . . ?
O3 C6 C5 128.6(3) . . ?
O3 C6 H6 115.8(19) . . ?
C5 C6 H6 115.6(19) . . ?
O2 C4 C5 124.8(3) . . ?
O2 C4 C10 117.1(3) . . ?
C5 C4 C10 118.1(3) . . ?
C8 C7 C14 116.9(3) . . ?
C8 C7 C5 119.6(3) . . ?
C14 C7 C5 123.5(3) . . ?
C7 C8 C11 120.7(3) . . ?
C7 C8 C9 119.5(3) . . ?
C11 C8 C9 119.8(3) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C10 C9 C8 121.6(3) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C12 C11 C8 120.6(4) . . ?
C12 C11 H11 119.7 . . ?
C8 C11 H11 119.7 . . ?
C9 C10 C4 121.9(3) . . ?
C9 C10 H10 119.0 . . ?
C4 C10 H10 119.0 . . ?
C11 C12 C13 119.4(4) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C13 C14 C7 121.1(3) . . ?
C13 C14 H14 119.5 . . ?
C7 C14 H14 119.5 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C14 C13 C12 121.2(4) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?

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
O2 Co1 O2 C4 -23(100) 2_666 . . . ?
O3 Co1 O2 C4 -169.1(2) 2_666 . . . ?
O3 Co1 O2 C4 10.9(2) . . . . ?
O1 Co1 O2 C4 101.2(2) 2_666 . . . ?
O1 Co1 O2 C4 -78.8(2) . . . . ?
O2 Co1 O1 C1 -28.0(2) 2_666 . . . ?
O2 Co1 O1 C1 152.0(2) . . . . ?
O3 Co1 O1 C1 -115.7(2) 2_666 . . . ?
O3 Co1 O1 C1 64.3(2) . . . . ?
O1 Co1 O1 C1 110(100) 2_666 . . . ?
O2 Co1 O3 C6 172.6(2) 2_666 . . . ?
O2 Co1 O3 C6 -7.4(2) . . . . ?
O3 Co1 O3 C6 58(100) 2_666 . . . ?
O1 Co1 O3 C6 -98.5(2) 2_666 . . . ?
O1 Co1 O3 C6 81.5(2) . . . . ?
Co1 O1 C1 N1 175.5(2) . . . . ?
C2 N1 C1 O1 -1.1(5) . . . . ?
C3 N1 C1 O1 -179.9(3) . . . . ?
Co1 O3 C6 C5 1.4(5) . . . . ?
C4 C5 C6 O3 5.3(5) . . . . ?
C7 C5 C6 O3 -177.9(3) . . . . ?
Co1 O2 C4 C5 -8.3(4) . . . . ?
Co1 O2 C4 C10 172.73(19) . . . . ?
C6 C5 C4 O2 -1.9(5) . . . . ?
C7 C5 C4 O2 -178.6(2) . . . . ?
C6 C5 C4 C10 177.1(3) . . . . ?
C7 C5 C4 C10 0.3(4) . . . . ?
C6 C5 C7 C8 -176.6(3) . . . . ?
C4 C5 C7 C8 0.2(4) . . . . ?
C6 C5 C7 C14 3.4(5) . . . . ?
C4 C5 C7 C14 -179.8(3) . . . . ?
C14 C7 C8 C11 -1.6(5) . . . . ?
C5 C7 C8 C11 178.4(3) . . . . ?
C14 C7 C8 C9 179.5(3) . . . . ?
C5 C7 C8 C9 -0.6(4) . . . . ?
C7 C8 C9 C10 0.4(5) . . . . ?
C11 C8 C9 C10 -178.6(3) . . . . ?
C7 C8 C11 C12 0.9(5) . . . . ?
C9 C8 C11 C12 179.9(3) . . . . ?
C8 C9 C10 C4 0.2(5) . . . . ?
O2 C4 C10 C9 178.5(3) . . . . ?
C5 C4 C10 C9 -0.5(4) . . . . ?
C8 C11 C12 C13 0.1(6) . . . . ?
C8 C7 C14 C13 1.2(5) . . . . ?
C5 C7 C14 C13 -178.7(3) . . . . ?
C7 C14 C13 C12 -0.2(6) . . . . ?
C11 C12 C13 C14 -0.5(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.940
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.940
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.067
