# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_RBS2
_database_code_depnum_ccdc_archive 'CCDC 1033010'
_audit_update_record             
;
2014-11-06 deposited with the CCDC.
2015-04-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H28 Co N2 O10'
_chemical_formula_sum            'C26 H28 Co N2 O10'
_chemical_formula_weight         587.43

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   6.270(4)
_cell_length_b                   7.007(3)
_cell_length_c                   15.402(5)
_cell_angle_alpha                97.886(5)
_cell_angle_beta                 95.917(5)
_cell_angle_gamma                114.306(5)
_cell_volume                     601.2(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      3.25
_cell_measurement_theta_max      25.50

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             305
_exptl_absorpt_coefficient_mu    0.780
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8723
_exptl_absorpt_correction_T_max  0.9122
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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            3237
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.25
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2196
_reflns_number_gt                1921
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0820P)²+0.2981P] 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         2196
_refine_ls_number_parameters     194
_refine_ls_number_restraints     23
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1423
_refine_ls_wR_factor_gt          0.1123
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_restrained_S_all      1.162
_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 0.5000 1.0000 0.0126(2) Uani 1 2 d S . .
O1 O 1.1920(4) 0.3190(4) 0.97736(15) 0.0145(5) Uani 1 1 d D . .
O5 O 0.0116(4) 0.0679(4) 0.14647(14) 0.0160(5) Uani 1 1 d . . .
O4 O 0.3821(4) 0.2314(4) 0.11962(14) 0.0157(5) Uani 1 1 d . . .
O3 O 0.6043(4) 0.2663(4) 0.53479(14) 0.0159(5) Uani 1 1 d . . .
C10 C 0.3319(6) 0.1874(5) 0.2673(2) 0.0132(7) Uani 1 1 d . . .
O2 O 1.2433(4) 0.7697(4) 0.95734(15) 0.0158(5) Uani 1 1 d D . .
C2 C 0.4600(6) 0.2549(5) 0.7607(2) 0.0153(7) Uani 1 1 d . . .
H2 H 0.2956 0.2052 0.7500 0.018 Uiso 1 1 calc R . .
C9 C 0.1816(6) 0.1644(5) 0.3295(2) 0.0140(7) Uani 1 1 d . . .
H9 H 0.0223 0.1306 0.3106 0.017 Uiso 1 1 calc R . .
C7 C 0.5040(6) 0.2417(5) 0.4484(2) 0.0141(7) Uani 1 1 d . . .
C4 C 0.8286(6) 0.3471(5) 0.7096(2) 0.0146(7) Uani 1 1 d . . .
H4 H 0.9180 0.3609 0.6643 0.018 Uiso 1 1 calc R . .
C6 C 0.4499(6) 0.2443(5) 0.5987(2) 0.0152(7) Uani 1 1 d . . .
H6A H 0.3200 0.1019 0.5844 0.018 Uiso 1 1 calc R . .
H6B H 0.3829 0.3465 0.5967 0.018 Uiso 1 1 calc R . .
N1 N 0.8177(5) 0.3738(4) 0.86597(17) 0.0118(6) Uani 1 1 d . . .
C13 C 0.2337(6) 0.1582(5) 0.1697(2) 0.0130(7) Uani 1 1 d . . .
C3 C 0.5851(6) 0.2820(5) 0.6902(2) 0.0148(7) Uani 1 1 d . . .
C5 C 0.9362(6) 0.3910(5) 0.7977(2) 0.0145(7) Uani 1 1 d . . .
H5 H 1.0996 0.4349 0.8101 0.017 Uiso 1 1 calc R . .
C1 C 0.5829(6) 0.3026(5) 0.8467(2) 0.0156(7) Uani 1 1 d . . .
H1 H 0.4972 0.2840 0.8932 0.019 Uiso 1 1 calc R . .
C8 C 0.2660(6) 0.1913(5) 0.4201(2) 0.0157(7) Uani 1 1 d . . .
H8 H 0.1638 0.1757 0.4610 0.019 Uiso 1 1 calc R . .
C11 C 0.5724(6) 0.2428(5) 0.2974(2) 0.0142(7) Uani 1 1 d . . .
H11 H 0.6760 0.2615 0.2568 0.017 Uiso 1 1 calc R . .
C12 C 0.6566(6) 0.2696(5) 0.3866(2) 0.0146(7) Uani 1 1 d . . .
H12 H 0.8166 0.3066 0.4058 0.018 Uiso 1 1 calc R . .
H1O1 H 1.250(7) 0.290(7) 1.021(2) 0.033(12) Uiso 1 1 d D . .
H1O2 H 1.382(4) 0.800(7) 0.945(3) 0.032(12) Uiso 1 1 d D . .
H2O1 H 1.117(9) 0.205(5) 0.937(2) 0.064(18) Uiso 1 1 d D . .
H202 H 1.171(9) 0.802(15) 0.917(4) 0.16(4) Uiso 1 1 d 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 O1 2.098(2) 2_767 ?
Co1 O1 2.098(2) . ?
Co1 O2 2.123(3) 2_767 ?
Co1 O2 2.123(3) . ?
Co1 N1 2.129(3) 2_767 ?
Co1 N1 2.129(3) . ?
O1 H1O1 0.82(4) . ?
O1 H2O1 0.86(2) . ?
O5 C13 1.256(4) . ?
O4 C13 1.260(4) . ?
O3 C7 1.368(4) . ?
O3 C6 1.431(4) . ?
C10 C9 1.392(5) . ?
C10 C11 1.401(5) . ?
C10 C13 1.517(4) . ?
O2 H1O2 0.855(14) . ?
O2 H202 0.84(2) . ?
C2 C1 1.385(5) . ?
C2 C3 1.392(5) . ?
C2 H2 0.9300 . ?
C9 C8 1.397(4) . ?
C9 H9 0.9300 . ?
C7 C8 1.390(5) . ?
C7 C12 1.394(5) . ?
C4 C5 1.384(4) . ?
C4 C3 1.387(5) . ?
C4 H4 0.9300 . ?
C6 C3 1.497(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
N1 C1 1.330(4) . ?
N1 C5 1.340(4) . ?
C5 H5 0.9300 . ?
C1 H1 0.9300 . ?
C8 H8 0.9300 . ?
C11 C12 1.379(4) . ?
C11 H11 0.9300 . ?
C12 H12 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
O1 Co1 O1 180.000(2) 2_767 . ?
O1 Co1 O2 94.63(11) 2_767 2_767 ?
O1 Co1 O2 85.37(11) . 2_767 ?
O1 Co1 O2 85.37(11) 2_767 . ?
O1 Co1 O2 94.63(11) . . ?
O2 Co1 O2 180.00(11) 2_767 . ?
O1 Co1 N1 88.46(10) 2_767 2_767 ?
O1 Co1 N1 91.54(10) . 2_767 ?
O2 Co1 N1 88.88(10) 2_767 2_767 ?
O2 Co1 N1 91.12(10) . 2_767 ?
O1 Co1 N1 91.54(10) 2_767 . ?
O1 Co1 N1 88.46(10) . . ?
O2 Co1 N1 91.12(10) 2_767 . ?
O2 Co1 N1 88.88(10) . . ?
N1 Co1 N1 180.000(1) 2_767 . ?
Co1 O1 H1O1 117(3) . . ?
Co1 O1 H2O1 114(4) . . ?
H1O1 O1 H2O1 110(4) . . ?
C7 O3 C6 116.0(3) . . ?
C9 C10 C11 118.6(3) . . ?
C9 C10 C13 119.5(3) . . ?
C11 C10 C13 121.9(3) . . ?
Co1 O2 H1O2 131(3) . . ?
Co1 O2 H202 110(5) . . ?
H1O2 O2 H202 106(3) . . ?
C1 C2 C3 119.3(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C10 C9 C8 121.1(3) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
O3 C7 C8 124.4(3) . . ?
O3 C7 C12 115.9(3) . . ?
C8 C7 C12 119.7(3) . . ?
C5 C4 C3 118.8(3) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
O3 C6 C3 110.0(3) . . ?
O3 C6 H6A 109.7 . . ?
C3 C6 H6A 109.7 . . ?
O3 C6 H6B 109.7 . . ?
C3 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C1 N1 C5 117.4(3) . . ?
C1 N1 Co1 120.6(2) . . ?
C5 N1 Co1 121.3(2) . . ?
O5 C13 O4 125.8(3) . . ?
O5 C13 C10 117.1(3) . . ?
O4 C13 C10 117.0(3) . . ?
C4 C3 C2 117.8(3) . . ?
C4 C3 C6 124.1(3) . . ?
C2 C3 C6 118.1(3) . . ?
N1 C5 C4 123.6(3) . . ?
N1 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
N1 C1 C2 123.0(3) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C7 C8 C9 119.4(3) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?

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
C11 C10 C9 C8 -1.3(5) . . . . ?
C13 C10 C9 C8 -179.7(3) . . . . ?
C6 O3 C7 C8 -2.1(4) . . . . ?
C6 O3 C7 C12 178.1(3) . . . . ?
C7 O3 C6 C3 -178.2(2) . . . . ?
O1 Co1 N1 C1 -45.4(2) 2_767 . . . ?
O1 Co1 N1 C1 134.6(2) . . . . ?
O2 Co1 N1 C1 49.3(2) 2_767 . . . ?
O2 Co1 N1 C1 -130.7(2) . . . . ?
N1 Co1 N1 C1 -91(100) 2_767 . . . ?
O1 Co1 N1 C5 125.0(2) 2_767 . . . ?
O1 Co1 N1 C5 -55.0(2) . . . . ?
O2 Co1 N1 C5 -140.3(2) 2_767 . . . ?
O2 Co1 N1 C5 39.7(2) . . . . ?
N1 Co1 N1 C5 79(100) 2_767 . . . ?
C9 C10 C13 O5 -15.7(4) . . . . ?
C11 C10 C13 O5 166.0(3) . . . . ?
C9 C10 C13 O4 162.6(3) . . . . ?
C11 C10 C13 O4 -15.7(4) . . . . ?
C5 C4 C3 C2 -2.9(5) . . . . ?
C5 C4 C3 C6 175.5(3) . . . . ?
C1 C2 C3 C4 2.9(5) . . . . ?
C1 C2 C3 C6 -175.7(3) . . . . ?
O3 C6 C3 C4 5.2(4) . . . . ?
O3 C6 C3 C2 -176.3(3) . . . . ?
C1 N1 C5 C4 2.6(5) . . . . ?
Co1 N1 C5 C4 -168.0(2) . . . . ?
C3 C4 C5 N1 0.2(5) . . . . ?
C5 N1 C1 C2 -2.7(5) . . . . ?
Co1 N1 C1 C2 168.1(2) . . . . ?
C3 C2 C1 N1 -0.1(5) . . . . ?
O3 C7 C8 C9 -178.3(3) . . . . ?
C12 C7 C8 C9 1.5(5) . . . . ?
C10 C9 C8 C7 -0.1(5) . . . . ?
C9 C10 C11 C12 1.2(5) . . . . ?
C13 C10 C11 C12 179.6(3) . . . . ?
C10 C11 C12 C7 0.1(5) . . . . ?
O3 C7 C12 C11 178.2(3) . . . . ?
C8 C7 C12 C11 -1.5(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.132
