# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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 1418239'
_audit_update_record             
;
2016-02-22 deposited with the CCDC.
2016-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H20 Co N6 O6 S'
_chemical_formula_weight         603.47

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           64
_space_group_name_H-M_alt        'C m c a'
_space_group_name_Hall           '-C 2bc 2'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   24.226(2)
_cell_length_b                   20.495(2)
_cell_length_c                   12.7686(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6339.8(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4244
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      24.69

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_density_meas      1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_F_000             2472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.652
_shelx_estimated_absorpt_T_min   0.828
_shelx_estimated_absorpt_T_max   0.870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8284
_exptl_absorpt_correction_T_max  0.8699
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20899
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.681
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3735
_reflns_number_gt                2764
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0909P)²+1.4249P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3735
_refine_ls_number_parameters     186
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1540
_refine_ls_wR_factor_gt          0.1453
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.098
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.2500 0.03941(2) 0.2500 0.04534(17) Uani 1 2 d S T P . .
S2 S 0.0000 0.25400(6) -0.06606(9) 0.0725(3) Uani 1 2 d S TU P . .
O1 O 0.20426(7) 0.05630(9) 0.10357(13) 0.0615(5) Uani 1 1 d . . . . .
O2 O 0.18925(9) 0.11587(9) 0.24124(13) 0.0639(5) Uani 1 1 d . . . . .
O3 O 0.0000 0.32059(15) -0.0263(3) 0.1022(10) Uani 1 2 d S TU P . .
O4 O 0.0000 0.2428(2) -0.1766(3) 0.1020(13) Uani 1 2 d S T P . .
N1 N 0.19663(8) -0.02502(9) 0.32041(16) 0.0506(5) Uani 1 1 d . . . . .
N2 N 0.12672(11) -0.09217(15) 0.3568(2) 0.0921(9) Uani 1 1 d . U . . .
N3 N 0.16793(8) -0.10019(9) 0.42927(15) 0.0497(5) Uani 1 1 d . U . . .
C1 C 0.14560(13) -0.04502(15) 0.2897(3) 0.0765(9) Uani 1 1 d . U . . .
H1 H 0.1265 -0.0291 0.2319 0.092 Uiso 1 1 calc R U . . .
C2 C 0.20849(9) -0.05935(11) 0.40357(18) 0.0483(5) Uani 1 1 d . . . . .
H2 H 0.2414 -0.0557 0.4405 0.058 Uiso 1 1 calc R U . . .
C3 C 0.16826(11) -0.14648(12) 0.51625(19) 0.0551(6) Uani 1 1 d . . . . .
H3A H 0.1321 -0.1666 0.5214 0.066 Uiso 1 1 calc R U . . .
H3B H 0.1748 -0.1228 0.5808 0.066 Uiso 1 1 calc R U . . .
C4 C 0.21106(10) -0.19945(11) 0.50611(17) 0.0467(5) Uani 1 1 d . . . . .
C5 C 0.23354(13) -0.21828(12) 0.41062(19) 0.0558(6) Uani 1 1 d . . . . .
H5 H 0.2228 -0.1968 0.3497 0.067 Uiso 1 1 calc R U . . .
C6 C 0.22851(12) -0.23169(13) 0.59501(18) 0.0553(6) Uani 1 1 d . . . . .
H6 H 0.2144 -0.2195 0.6599 0.066 Uiso 1 1 calc R U . . .
C7 C 0.17963(9) 0.10162(11) 0.14747(18) 0.0473(5) Uani 1 1 d . . . . .
C8 C 0.13727(9) 0.14164(12) 0.08974(17) 0.0475(5) Uani 1 1 d . . . . .
C9 C 0.12349(10) 0.12655(14) -0.01228(19) 0.0628(7) Uani 1 1 d . . . . .
H9 H 0.1415 0.0930 -0.0475 0.075 Uiso 1 1 calc R U . . .
C10 C 0.08189(11) 0.16255(16) -0.0620(2) 0.0692(8) Uani 1 1 d . . . . .
H10 H 0.0715 0.1527 -0.1303 0.083 Uiso 1 1 calc R U . . .
C11 C 0.05670(10) 0.21235(13) -0.0088(2) 0.0559(6) Uani 1 1 d . . . . .
C12 C 0.07105(11) 0.22826(13) 0.0915(2) 0.0608(7) Uani 1 1 d . . . . .
H12 H 0.0537 0.2626 0.1260 0.073 Uiso 1 1 calc R U . . .
C13 C 0.11183(11) 0.19234(13) 0.1406(2) 0.0576(6) Uani 1 1 d . . . . .
H13 H 0.1221 0.2027 0.2088 0.069 Uiso 1 1 calc R U . . .


_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 N1 2.055(2) 8_545 ?
Co1 N1 2.055(2) . ?
Co1 O2 2.153(2) . ?
Co1 O2 2.153(2) 8_545 ?
Co1 O1 2.2009(17) 8_545 ?
Co1 O1 2.2009(17) . ?
Co1 C7 2.499(2) 8_545 ?
S2 O4 1.430(4) . ?
S2 O3 1.456(4) . ?
S2 C11 1.775(2) . ?
S2 C11 1.775(2) 11 ?
O1 C7 1.238(3) . ?
O2 C7 1.254(3) . ?
N1 C2 1.306(3) . ?
N1 C1 1.360(3) . ?
N2 C1 1.370(4) . ?
N2 N3 1.371(3) . ?
N3 C2 1.332(3) . ?
N3 C3 1.461(3) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 C4 1.507(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C6 1.380(3) . ?
C4 C5 1.390(3) . ?
C5 C6 1.379(4) 13_546 ?
C5 H5 0.9300 . ?
C6 C5 1.379(4) 13_546 ?
C6 H6 0.9300 . ?
C7 C8 1.506(3) . ?
C8 C13 1.372(3) . ?
C8 C9 1.380(3) . ?
C9 C10 1.401(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.370(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.366(4) . ?
C12 C13 1.383(4) . ?
C12 H12 0.9300 . ?
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
N1 Co1 N1 100.03(11) 8_545 . ?
N1 Co1 O2 151.06(7) 8_545 . ?
N1 Co1 O2 93.46(8) . . ?
N1 Co1 O2 93.46(8) 8_545 8_545 ?
N1 Co1 O2 151.06(7) . 8_545 ?
O2 Co1 O2 86.58(11) . 8_545 ?
N1 Co1 O1 98.97(7) 8_545 8_545 ?
N1 Co1 O1 92.65(7) . 8_545 ?
O2 Co1 O1 105.90(7) . 8_545 ?
O2 Co1 O1 59.81(6) 8_545 8_545 ?
N1 Co1 O1 92.65(7) 8_545 . ?
N1 Co1 O1 98.97(7) . . ?
O2 Co1 O1 59.81(6) . . ?
O2 Co1 O1 105.90(7) 8_545 . ?
O1 Co1 O1 161.91(10) 8_545 . ?
N1 Co1 C7 97.35(8) 8_545 8_545 ?
N1 Co1 C7 121.86(8) . 8_545 ?
O2 Co1 C7 97.02(7) . 8_545 ?
O2 Co1 C7 30.12(7) 8_545 8_545 ?
O1 Co1 C7 29.69(7) 8_545 8_545 ?
O1 Co1 C7 135.10(8) . 8_545 ?
O4 S2 O3 119.7(2) . . ?
O4 S2 C11 109.22(15) . . ?
O3 S2 C11 107.87(14) . . ?
O4 S2 C11 109.23(15) . 11 ?
O3 S2 C11 107.87(14) . 11 ?
C11 S2 C11 101.39(15) . 11 ?
C7 O1 Co1 88.62(14) . . ?
C7 O2 Co1 90.41(15) . . ?
C2 N1 C1 105.8(2) . . ?
C2 N1 Co1 124.30(15) . . ?
C1 N1 Co1 129.73(19) . . ?
C1 N2 N3 105.3(2) . . ?
C2 N3 N2 107.2(2) . . ?
C2 N3 C3 126.3(2) . . ?
N2 N3 C3 126.5(2) . . ?
N1 C1 N2 109.6(3) . . ?
N1 C1 H1 125.2 . . ?
N2 C1 H1 125.2 . . ?
N1 C2 N3 112.1(2) . . ?
N1 C2 H2 123.9 . . ?
N3 C2 H2 123.9 . . ?
N3 C3 C4 113.98(19) . . ?
N3 C3 H3A 108.8 . . ?
C4 C3 H3A 108.8 . . ?
N3 C3 H3B 108.8 . . ?
C4 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C6 C4 C5 117.9(2) . . ?
C6 C4 C3 119.0(2) . . ?
C5 C4 C3 123.0(2) . . ?
C6 C5 C4 120.9(2) 13_546 . ?
C6 C5 H5 119.6 13_546 . ?
C4 C5 H5 119.6 . . ?
C5 C6 C4 121.2(2) 13_546 . ?
C5 C6 H6 119.4 13_546 . ?
C4 C6 H6 119.4 . . ?
O1 C7 O2 121.2(2) . . ?
O1 C7 C8 121.0(2) . . ?
O2 C7 C8 117.8(2) . . ?
C13 C8 C9 120.5(2) . . ?
C13 C8 C7 119.1(2) . . ?
C9 C8 C7 120.3(2) . . ?
C8 C9 C10 118.9(2) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C11 C10 C9 119.2(2) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C12 C11 C10 122.0(2) . . ?
C12 C11 S2 117.9(2) . . ?
C10 C11 S2 119.9(2) . . ?
C11 C12 C13 118.7(3) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C8 C13 C12 120.6(2) . . ?
C8 C13 H13 119.7 . . ?
C12 C13 H13 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
C1 N2 N3 C2 -0.3(3) . . . . ?
C1 N2 N3 C3 -178.3(3) . . . . ?
C2 N1 C1 N2 0.3(4) . . . . ?
Co1 N1 C1 N2 175.6(2) . . . . ?
N3 N2 C1 N1 0.0(4) . . . . ?
C1 N1 C2 N3 -0.5(3) . . . . ?
Co1 N1 C2 N3 -176.10(15) . . . . ?
N2 N3 C2 N1 0.5(3) . . . . ?
C3 N3 C2 N1 178.5(2) . . . . ?
C2 N3 C3 C4 -64.6(3) . . . . ?
N2 N3 C3 C4 113.1(3) . . . . ?
N3 C3 C4 C6 158.1(2) . . . . ?
N3 C3 C4 C5 -22.8(3) . . . . ?
C6 C4 C5 C6 0.9(4) . . . 13_546 ?
C3 C4 C5 C6 -178.2(2) . . . 13_546 ?
C5 C4 C6 C5 -0.9(4) . . . 13_546 ?
C3 C4 C6 C5 178.2(2) . . . 13_546 ?
Co1 O1 C7 O2 -0.6(2) . . . . ?
Co1 O1 C7 C8 179.20(19) . . . . ?
Co1 O2 C7 O1 0.6(2) . . . . ?
Co1 O2 C7 C8 -179.19(18) . . . . ?
O1 C7 C8 C13 -178.6(2) . . . . ?
O2 C7 C8 C13 1.2(3) . . . . ?
O1 C7 C8 C9 2.7(4) . . . . ?
O2 C7 C8 C9 -177.5(2) . . . . ?
C13 C8 C9 C10 -2.0(4) . . . . ?
C7 C8 C9 C10 176.7(2) . . . . ?
C8 C9 C10 C11 1.1(4) . . . . ?
C9 C10 C11 C12 0.3(4) . . . . ?
C9 C10 C11 S2 -174.7(2) . . . . ?
O4 S2 C11 C12 165.9(2) . . . . ?
O3 S2 C11 C12 34.3(3) . . . . ?
C11 S2 C11 C12 -78.9(3) 11 . . . ?
O4 S2 C11 C10 -19.0(3) . . . . ?
O3 S2 C11 C10 -150.6(2) . . . . ?
C11 S2 C11 C10 96.2(2) 11 . . . ?
C10 C11 C12 C13 -0.7(4) . . . . ?
S2 C11 C12 C13 174.3(2) . . . . ?
C9 C8 C13 C12 1.5(4) . . . . ?
C7 C8 C13 C12 -177.2(2) . . . . ?
C11 C12 C13 C8 -0.2(4) . . . . ?

_refine_diff_density_max         1.097
_refine_diff_density_min         -0.644
_refine_diff_density_rms         0.054
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 -0.009 352 70 ' '
2 0.500 0.000 -0.008 352 70 ' '
3 0.500 0.500 -0.014 352 70 ' '
4 0.000 0.500 -0.007 352 70 ' '
_platon_squeeze_details          
;
;

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1418240'
_audit_update_record             
;
2016-02-22 deposited with the CCDC.
2016-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H15 Co N2 O6 S'
_chemical_formula_weight         482.34

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0828(7)
_cell_length_b                   12.9378(13)
_cell_length_c                   12.9943(13)
_cell_angle_alpha                109.3550(10)
_cell_angle_beta                 92.9220(10)
_cell_angle_gamma                101.7330(10)
_cell_volume                     1090.90(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7157
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      27.63

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_F_000             492
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.922
_shelx_estimated_absorpt_T_min   0.721
_shelx_estimated_absorpt_T_max   0.770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7209
_exptl_absorpt_correction_T_max  0.7695
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9991
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.675
_diffrn_reflns_theta_max         27.640
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             5001
_reflns_number_gt                4706
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0800P)²+0.5762P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5001
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.1143
_refine_ls_wR_factor_gt          0.1131
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.31124(3) 0.42431(2) 0.47117(2) 0.01117(10) Uani 1 1 d . . . . .
S1 S 0.85906(7) 0.13123(4) -0.11000(3) 0.01654(12) Uani 1 1 d . . . . .
O8 O 0.7317(2) 0.01998(11) -0.14716(11) 0.0242(3) Uani 1 1 d . . . . .
O9 O 1.0665(2) 0.14313(13) -0.10551(11) 0.0226(3) Uani 1 1 d . . . . .
O4 O 0.4927(2) 0.37088(12) 0.35120(11) 0.0202(3) Uani 1 1 d . . . . .
O5 O 0.7857(2) 0.48902(11) 0.38866(11) 0.0179(3) Uani 1 1 d . . . . .
O7 O 0.73811(19) 0.46783(11) -0.39485(11) 0.0164(3) Uani 1 1 d . . . . .
O6 O 0.44174(19) 0.35068(11) -0.43646(11) 0.0179(3) Uani 1 1 d . . . . .
N1 N 0.0938(2) 0.28497(12) 0.39484(12) 0.0123(3) Uani 1 1 d . . . . .
N2 N -0.2010(2) 0.17485(12) 0.35706(12) 0.0138(3) Uani 1 1 d . . . . .
C16 C -0.0852(3) 0.27390(14) 0.42200(14) 0.0125(3) Uani 1 1 d . . . . .
H16 H -0.1255 0.3275 0.4785 0.015 Uiso 1 1 calc R U . . .
C9 C 0.7883(3) 0.20527(15) -0.19305(14) 0.0154(3) Uani 1 1 d . . . . .
C7 C 0.8047(3) 0.20708(15) 0.02148(14) 0.0165(3) Uani 1 1 d . . . . .
C5 C 0.9017(3) 0.35623(15) 0.19545(14) 0.0155(3) Uani 1 1 d . . . . .
H5 H 0.9970 0.4134 0.2461 0.019 Uiso 1 1 calc R U . . .
C2 C 0.6596(3) 0.40400(15) 0.32825(14) 0.0151(3) Uani 1 1 d . . . . .
C22 C -0.6434(3) 0.03079(15) 0.44829(16) 0.0173(3) Uani 1 1 d . . . . .
H22 H -0.7403 0.0512 0.4136 0.021 Uiso 1 1 calc R U . . .
C3 C 0.7122(3) 0.33439(15) 0.22005(14) 0.0152(3) Uani 1 1 d . . . . .
C19 C -0.4076(3) 0.13583(16) 0.36178(16) 0.0168(3) Uani 1 1 d . . . . .
H19A H -0.4712 0.0912 0.2879 0.020 Uiso 1 1 calc R U . . .
H19B H -0.4636 0.2008 0.3883 0.020 Uiso 1 1 calc R U . . .
C18 C -0.0893(3) 0.11861(15) 0.28447(15) 0.0157(3) Uani 1 1 d . . . . .
H18 H -0.1298 0.0479 0.2299 0.019 Uiso 1 1 calc R U . . .
C15 C 0.6130(3) 0.38597(15) -0.38844(14) 0.0138(3) Uani 1 1 d . . . . .
C20 C -0.4501(3) 0.06615(14) 0.43470(14) 0.0147(3) Uani 1 1 d . . . . .
C12 C 0.6761(3) 0.32225(15) -0.31931(14) 0.0143(3) Uani 1 1 d . . . . .
C6 C 0.9489(3) 0.29265(16) 0.09523(15) 0.0167(3) Uani 1 1 d . . . . .
H6 H 1.0750 0.3072 0.0779 0.020 Uiso 1 1 calc R U . . .
C14 C 0.9304(3) 0.27614(16) -0.22400(15) 0.0171(3) Uani 1 1 d . . . . .
H14 H 1.0614 0.2839 -0.2027 0.021 Uiso 1 1 calc R U . . .
C10 C 0.5906(3) 0.19108(16) -0.22446(15) 0.0189(4) Uani 1 1 d . . . . .
H10 H 0.4975 0.1434 -0.2027 0.023 Uiso 1 1 calc R U . . .
C11 C 0.5359(3) 0.24928(16) -0.28850(15) 0.0177(4) Uani 1 1 d . . . . .
H11 H 0.4049 0.2397 -0.3112 0.021 Uiso 1 1 calc R U . . .
C17 C 0.0921(3) 0.18732(15) 0.30865(14) 0.0151(3) Uani 1 1 d . . . . .
H17 H 0.1984 0.1711 0.2727 0.018 Uiso 1 1 calc R U . . .
C8 C 0.6150(3) 0.18230(17) 0.04514(16) 0.0237(4) Uani 1 1 d . . . . .
H8 H 0.5210 0.1237 -0.0049 0.028 Uiso 1 1 calc R U . . .
C4 C 0.5690(3) 0.24692(18) 0.14497(16) 0.0232(4) Uani 1 1 d . . . . .
H4 H 0.4427 0.2321 0.1621 0.028 Uiso 1 1 calc R U . . .
C13 C 0.8734(3) 0.33554(16) -0.28763(15) 0.0172(3) Uani 1 1 d . . . . .
H13 H 0.9666 0.3838 -0.3088 0.021 Uiso 1 1 calc R U . . .
C21 C -0.3068(3) 0.03468(16) 0.48683(15) 0.0173(4) Uani 1 1 d . . . . .
H21 H -0.1771 0.0575 0.4783 0.021 Uiso 1 1 calc R U . . .


_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 O5 2.0331(13) 2_666 ?
Co1 O7 2.0331(13) 2_665 ?
Co1 N1 2.0337(15) . ?
Co1 O6 2.0507(13) 1_556 ?
Co1 O4 2.1001(13) . ?
Co1 Co1 2.8706(5) 2_666 ?
S1 O9 1.4422(15) . ?
S1 O8 1.4441(15) . ?
S1 C7 1.7719(18) . ?
S1 C9 1.7773(17) . ?
O4 C2 1.259(2) . ?
O5 C2 1.257(2) . ?
O5 Co1 2.0330(13) 2_666 ?
O7 C15 1.264(2) . ?
O7 Co1 2.0330(13) 2_665 ?
O6 C15 1.256(2) . ?
O6 Co1 2.0508(13) 1_554 ?
N1 C16 1.326(2) . ?
N1 C17 1.380(2) . ?
N2 C16 1.346(2) . ?
N2 C18 1.379(2) . ?
N2 C19 1.459(2) . ?
C16 H16 0.9300 . ?
C9 C14 1.388(3) . ?
C9 C10 1.395(3) . ?
C7 C6 1.387(3) . ?
C7 C8 1.391(3) . ?
C5 C6 1.389(2) . ?
C5 C3 1.390(2) . ?
C5 H5 0.9300 . ?
C2 C3 1.509(2) . ?
C22 C21 1.391(3) 2_456 ?
C22 C20 1.392(2) . ?
C22 H22 0.9300 . ?
C3 C4 1.401(3) . ?
C19 C20 1.512(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C18 C17 1.360(2) . ?
C18 H18 0.9300 . ?
C15 C12 1.512(2) . ?
C20 C21 1.391(2) . ?
C12 C11 1.395(3) . ?
C12 C13 1.396(3) . ?
C6 H6 0.9300 . ?
C14 C13 1.397(2) . ?
C14 H14 0.9300 . ?
C10 C11 1.382(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C17 H17 0.9300 . ?
C8 C4 1.387(3) . ?
C8 H8 0.9300 . ?
C4 H4 0.9300 . ?
C13 H13 0.9300 . ?
C21 C22 1.391(3) 2_456 ?
C21 H21 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
O5 Co1 O7 92.82(5) 2_666 2_665 ?
O5 Co1 N1 105.52(6) 2_666 . ?
O7 Co1 N1 102.77(6) 2_665 . ?
O5 Co1 O6 86.91(5) 2_666 1_556 ?
O7 Co1 O6 162.34(6) 2_665 1_556 ?
N1 Co1 O6 94.28(6) . 1_556 ?
O5 Co1 O4 162.13(6) 2_666 . ?
O7 Co1 O4 86.65(5) 2_665 . ?
N1 Co1 O4 91.99(6) . . ?
O6 Co1 O4 88.25(6) 1_556 . ?
O5 Co1 Co1 92.88(4) 2_666 2_666 ?
O7 Co1 Co1 81.31(4) 2_665 2_666 ?
N1 Co1 Co1 160.80(4) . 2_666 ?
O6 Co1 Co1 81.07(4) 1_556 2_666 ?
O4 Co1 Co1 69.36(4) . 2_666 ?
O9 S1 O8 119.51(9) . . ?
O9 S1 C7 108.93(9) . . ?
O8 S1 C7 107.79(9) . . ?
O9 S1 C9 108.28(9) . . ?
O8 S1 C9 108.16(9) . . ?
C7 S1 C9 102.93(8) . . ?
C2 O4 Co1 139.44(13) . . ?
C2 O5 Co1 112.77(12) . 2_666 ?
C15 O7 Co1 125.83(12) . 2_665 ?
C15 O6 Co1 125.50(12) . 1_554 ?
C16 N1 C17 105.94(14) . . ?
C16 N1 Co1 123.26(12) . . ?
C17 N1 Co1 130.79(12) . . ?
C16 N2 C18 107.39(15) . . ?
C16 N2 C19 125.99(15) . . ?
C18 N2 C19 126.61(15) . . ?
N1 C16 N2 111.06(15) . . ?
N1 C16 H16 124.5 . . ?
N2 C16 H16 124.5 . . ?
C14 C9 C10 121.88(16) . . ?
C14 C9 S1 119.25(14) . . ?
C10 C9 S1 118.86(14) . . ?
C6 C7 C8 122.07(17) . . ?
C6 C7 S1 119.37(14) . . ?
C8 C7 S1 118.48(14) . . ?
C6 C5 C3 120.03(17) . . ?
C6 C5 H5 120.0 . . ?
C3 C5 H5 120.0 . . ?
O5 C2 O4 125.29(17) . . ?
O5 C2 C3 117.83(16) . . ?
O4 C2 C3 116.87(16) . . ?
C21 C22 C20 120.74(17) 2_456 . ?
C21 C22 H22 119.6 2_456 . ?
C20 C22 H22 119.6 . . ?
C5 C3 C4 120.23(17) . . ?
C5 C3 C2 120.27(16) . . ?
C4 C3 C2 119.49(16) . . ?
N2 C19 C20 114.15(15) . . ?
N2 C19 H19A 108.7 . . ?
C20 C19 H19A 108.7 . . ?
N2 C19 H19B 108.7 . . ?
C20 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
C17 C18 N2 106.21(15) . . ?
C17 C18 H18 126.9 . . ?
N2 C18 H18 126.9 . . ?
O6 C15 O7 126.01(16) . . ?
O6 C15 C12 116.68(16) . . ?
O7 C15 C12 117.28(15) . . ?
C21 C20 C22 118.96(16) . . ?
C21 C20 C19 123.35(16) . . ?
C22 C20 C19 117.68(16) . . ?
C11 C12 C13 120.33(16) . . ?
C11 C12 C15 119.55(16) . . ?
C13 C12 C15 120.12(16) . . ?
C7 C6 C5 118.92(17) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C9 C14 C13 118.89(17) . . ?
C9 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C11 C10 C9 118.75(17) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C10 C11 C12 120.40(17) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C18 C17 N1 109.39(15) . . ?
C18 C17 H17 125.3 . . ?
N1 C17 H17 125.3 . . ?
C4 C8 C7 118.57(18) . . ?
C4 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C8 C4 C3 120.16(18) . . ?
C8 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C12 C13 C14 119.73(17) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C22 C21 C20 120.29(16) 2_456 . ?
C22 C21 H21 119.9 2_456 . ?
C20 C21 H21 119.9 . . ?

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
C17 N1 C16 N2 -0.54(19) . . . . ?
Co1 N1 C16 N2 178.65(11) . . . . ?
C18 N2 C16 N1 0.5(2) . . . . ?
C19 N2 C16 N1 -178.40(15) . . . . ?
O9 S1 C9 C14 -10.86(17) . . . . ?
O8 S1 C9 C14 -141.72(15) . . . . ?
C7 S1 C9 C14 104.37(16) . . . . ?
O9 S1 C9 C10 169.69(14) . . . . ?
O8 S1 C9 C10 38.83(17) . . . . ?
C7 S1 C9 C10 -75.08(16) . . . . ?
O9 S1 C7 C6 21.24(17) . . . . ?
O8 S1 C7 C6 152.30(15) . . . . ?
C9 S1 C7 C6 -93.53(16) . . . . ?
O9 S1 C7 C8 -162.00(16) . . . . ?
O8 S1 C7 C8 -30.94(18) . . . . ?
C9 S1 C7 C8 83.23(17) . . . . ?
Co1 O5 C2 O4 -2.7(2) 2_666 . . . ?
Co1 O5 C2 C3 178.31(11) 2_666 . . . ?
Co1 O4 C2 O5 7.4(3) . . . . ?
Co1 O4 C2 C3 -173.57(13) . . . . ?
C6 C5 C3 C4 1.3(3) . . . . ?
C6 C5 C3 C2 -179.33(16) . . . . ?
O5 C2 C3 C5 7.9(2) . . . . ?
O4 C2 C3 C5 -171.21(16) . . . . ?
O5 C2 C3 C4 -172.68(17) . . . . ?
O4 C2 C3 C4 8.2(3) . . . . ?
C16 N2 C19 C20 -92.3(2) . . . . ?
C18 N2 C19 C20 89.0(2) . . . . ?
C16 N2 C18 C17 -0.2(2) . . . . ?
C19 N2 C18 C17 178.64(16) . . . . ?
Co1 O6 C15 O7 -5.2(3) 1_554 . . . ?
Co1 O6 C15 C12 176.63(11) 1_554 . . . ?
Co1 O7 C15 O6 7.1(3) 2_665 . . . ?
Co1 O7 C15 C12 -174.79(11) 2_665 . . . ?
C21 C22 C20 C21 0.2(3) 2_456 . . . ?
C21 C22 C20 C19 179.23(17) 2_456 . . . ?
N2 C19 C20 C21 -4.4(3) . . . . ?
N2 C19 C20 C22 176.63(16) . . . . ?
O6 C15 C12 C11 -16.4(2) . . . . ?
O7 C15 C12 C11 165.29(17) . . . . ?
O6 C15 C12 C13 162.91(16) . . . . ?
O7 C15 C12 C13 -15.4(2) . . . . ?
C8 C7 C6 C5 -0.6(3) . . . . ?
S1 C7 C6 C5 176.05(14) . . . . ?
C3 C5 C6 C7 -0.6(3) . . . . ?
C10 C9 C14 C13 0.5(3) . . . . ?
S1 C9 C14 C13 -178.88(14) . . . . ?
C14 C9 C10 C11 0.2(3) . . . . ?
S1 C9 C10 C11 179.62(14) . . . . ?
C9 C10 C11 C12 -1.1(3) . . . . ?
C13 C12 C11 C10 1.3(3) . . . . ?
C15 C12 C11 C10 -179.39(16) . . . . ?
N2 C18 C17 N1 -0.1(2) . . . . ?
C16 N1 C17 C18 0.37(19) . . . . ?
Co1 N1 C17 C18 -178.73(12) . . . . ?
C6 C7 C8 C4 1.2(3) . . . . ?
S1 C7 C8 C4 -175.49(16) . . . . ?
C7 C8 C4 C3 -0.5(3) . . . . ?
C5 C3 C4 C8 -0.7(3) . . . . ?
C2 C3 C4 C8 179.92(18) . . . . ?
C11 C12 C13 C14 -0.5(3) . . . . ?
C15 C12 C13 C14 -179.85(16) . . . . ?
C9 C14 C13 C12 -0.4(3) . . . . ?
C22 C20 C21 C22 -0.2(3) . . . 2_456 ?
C19 C20 C21 C22 -179.18(17) . . . 2_456 ?

_refine_diff_density_max         0.594
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.107
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.034 0.500 1.000 141 29 ' '
_platon_squeeze_details          
;
;
_shelxl_version_number           2014-3

