# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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. 
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data_120kR
_database_code_depnum_ccdc_archive 'CCDC 1832566'
_audit_update_record             
;
2018-04-25 deposited with the CCDC.
2018-04-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        MS001
_chemical_name_common            1-pink
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H8 Co0.25 N1.50 O0.50 S0.50'
_chemical_formula_weight         115.88

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           63
_space_group_name_H-M_alt        'C m c m'
_space_group_name_Hall           '-C 2c 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, z+1/2'
'x, -y, -z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, y, -z-1/2'
'-x, y, z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, -z-1/2'
'-x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   7.2068(7)
_cell_length_b                   14.2130(10)
_cell_length_c                   21.8914(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2242.3(3)
_cell_formula_units_Z            16
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3185
_cell_measurement_theta_min      3.0132
_cell_measurement_theta_max      27.4835

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_F_000             980
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.670
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.974
_shelx_estimated_absorpt_T_min   0.561
_shelx_estimated_absorpt_T_max   0.852
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_min  0.7397
_exptl_absorpt_correction_T_max  0.8802
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
;
Mercury (2x2 bin mode)
;
_diffrn_measurement_method       dtintegrate.ref
_diffrn_detector_area_resol_mean 14.7275
_diffrn_reflns_number            7051
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.014
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_full        25.241
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             1371
_reflns_number_gt                1241
_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       Crystalclear
_computing_cell_refinement       Crystalclear
_computing_data_reduction        Crystalclear
_computing_structure_solution    Yadokari
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    pymol
_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)+(0.0764P)²+5.4572P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1371
_refine_ls_number_parameters     130
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1340
_refine_ls_wR_factor_gt          0.1296
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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
N1 N 0.000000 0.1029(2) 0.43271(13) 0.0266(6) Uani 1 2 d S T P . .
C1 C 0.000000 0.1620(2) 0.39631(15) 0.0262(7) Uani 1 2 d S T P . .
S1 S 0.000000 0.24367(8) 0.34407(5) 0.0485(3) Uani 1 2 d S T P . .
N2 N -0.3177(4) 0.000000 0.500000 0.0173(6) Uani 1 2 d S T P . .
C2 C -0.3931(8) -0.0142(5) 0.5619(2) 0.0399(15) Uani 0.5 1 d . . P . .
H8 H -0.349(10) 0.036(6) 0.587(3) 0.041(18) Uiso 0.5 1 d . . P . .
H9 H -0.337(10) -0.041(5) 0.585(4) 0.04(2) Uiso 0.5 1 d . . P . .
C3 C -0.3932(7) -0.0851(4) 0.5251(3) 0.0405(15) Uani 0.5 1 d . . P . .
H10 H -0.347(6) -0.099(3) 0.570(2) 0.003(9) Uiso 0.5 1 d . . P . .
H11 H -0.341(9) -0.134(5) 0.514(3) 0.038(18) Uiso 0.5 1 d . . P . .
C4 C -0.3924(7) -0.0811(4) 0.4626(3) 0.0355(12) Uani 0.5 1 d . . P . .
H12 H -0.351(7) -0.138(4) 0.482(3) 0.014(12) Uiso 0.5 1 d . . P . .
H13 H -0.346(9) -0.089(5) 0.424(3) 0.041(18) Uiso 0.5 1 d . . P . .
O1 O 0.000000 0.09944(17) 0.56958(11) 0.0255(5) Uani 1 2 d S T P . .
H1 H 0.000000 0.085(3) 0.606(2) 0.040(12) Uiso 1 2 d S . P . .
C5 C 0.000000 0.1996(3) 0.56461(17) 0.0355(8) Uani 1 2 d S T P . .
H5 H 0.109(4) 0.225(2) 0.5859(16) 0.042(8) Uiso 1 1 d . . . . .
H5A H 0.000000 0.208(3) 0.517(2) 0.046(13) Uiso 1 2 d S . P . .
N3 N 0.000000 0.0728(3) 0.69119(14) 0.0413(8) Uani 1 2 d S T P . .
C6 C 0.1666(5) 0.0239(3) 0.71452(12) 0.0460(7) Uani 1 1 d . . . . .
H6 H 0.275(5) 0.058(2) 0.6995(15) 0.047(9) Uiso 1 1 d . . . . .
H6A H 0.166(4) -0.037(2) 0.7001(15) 0.038(8) Uiso 1 1 d . . . . .
C7 C 0.000000 0.1704(3) 0.71485(18) 0.0486(10) Uani 1 2 d S T P . .
H7 H -0.111208 0.203951 0.699716 0.058 Uiso 0.5 1 calc R U P . .
H7A H 0.111208 0.203951 0.699716 0.058 Uiso 0.5 1 calc R U P . .
Co1 Co 0.000000 0.000000 0.500000 0.0204(2) Uani 1 4 d S T P . .


_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
N1 C1 1.157(4) . ?
N1 Co1 2.076(3) . ?
C1 S1 1.629(3) . ?
N2 C3 1.436(5) . ?
N2 C3 1.436(5) 3_556 ?
N2 C2 1.474(5) . ?
N2 C2 1.474(5) 3_556 ?
N2 C4 1.513(5) 3_556 ?
N2 C4 1.513(5) . ?
N2 Co1 2.290(3) . ?
C2 C2 1.541(11) 11_455 ?
C2 H8 0.95(8) . ?
C2 H9 0.76(7) . ?
C3 C3 1.539(9) 11_455 ?
C3 H10 1.05(5) . ?
C3 H11 0.83(7) . ?
C4 C4 1.551(9) 11_455 ?
C4 H12 0.96(5) . ?
C4 H13 0.92(7) . ?
O1 C5 1.427(4) . ?
O1 Co1 2.078(2) . ?
O1 H1 0.82(5) . ?
C5 H5 0.98(3) . ?
C5 H5A 1.05(5) . ?
C5 H5 0.98(3) 11 ?
N3 C6 1.478(4) 11 ?
N3 C6 1.478(4) . ?
N3 C7 1.481(6) . ?
C6 C6 1.554(5) 10_557 ?
C6 H6 0.98(4) . ?
C6 H6A 0.92(3) . ?
C7 C7 1.539(8) 10_557 ?
C7 H7 0.9900 . ?
C7 H7A 0.9900 . ?

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
C1 N1 Co1 178.3(3) . . ?
N1 C1 S1 178.9(3) . . ?
C3 N2 C3 135.4(4) . 3_556 ?
C3 N2 C2 52.6(4) . . ?
C3 N2 C2 109.1(4) 3_556 . ?
C3 N2 C2 109.1(4) . 3_556 ?
C3 N2 C2 52.6(4) 3_556 3_556 ?
C2 N2 C2 136.7(5) . 3_556 ?
C3 N2 C4 107.4(4) . 3_556 ?
C3 N2 C4 55.3(4) 3_556 3_556 ?
C2 N2 C4 58.4(4) . 3_556 ?
C2 N2 C4 105.2(4) 3_556 3_556 ?
C3 N2 C4 55.3(4) . . ?
C3 N2 C4 107.4(4) 3_556 . ?
C2 N2 C4 105.2(4) . . ?
C2 N2 C4 58.4(4) 3_556 . ?
C4 N2 C4 138.3(4) 3_556 . ?
C3 N2 Co1 112.3(2) . . ?
C3 N2 Co1 112.3(2) 3_556 . ?
C2 N2 Co1 111.6(2) . . ?
C2 N2 Co1 111.6(2) 3_556 . ?
C4 N2 Co1 110.8(2) 3_556 . ?
C4 N2 Co1 110.8(2) . . ?
C4 C2 N2 62.1(3) 3_556 . ?
C4 C2 C2 90.2(3) 3_556 11_455 ?
N2 C2 C2 111.6(2) . 11_455 ?
C4 C2 C3 108.7(4) 3_556 11_455 ?
N2 C2 C3 89.0(3) . 11_455 ?
C2 C2 C3 39.9(3) 11_455 11_455 ?
C4 C2 H8 61(5) 3_556 . ?
N2 C2 H8 108(5) . . ?
C2 C2 H8 109(4) 11_455 . ?
C3 C2 H8 149(4) 11_455 . ?
C4 C2 H9 136(6) 3_556 . ?
N2 C2 H9 120(6) . . ?
C2 C2 H9 122(5) 11_455 . ?
C3 C2 H9 115(6) 11_455 . ?
H8 C2 H9 80(7) . . ?
C4 C2 H10 159(2) 3_556 . ?
N2 C2 H10 99(2) . . ?
C2 C2 H10 105(2) 11_455 . ?
C3 C2 H10 77(2) 11_455 . ?
H8 C2 H10 124(5) . . ?
H9 C2 H10 44(6) . . ?
N2 C3 C3 112.3(2) . 11_455 ?
N2 C3 C2 91.3(3) . 11_455 ?
C3 C3 C2 39.9(3) 11_455 11_455 ?
N2 C3 H9 83(3) . . ?
C3 C3 H9 106(3) 11_455 . ?
C2 C3 H9 70(3) 11_455 . ?
N2 C3 H10 113(3) . . ?
C3 C3 H10 109(2) 11_455 . ?
C2 C3 H10 88(2) 11_455 . ?
H9 C3 H10 35(3) . . ?
N2 C3 H11 115(5) . . ?
C3 C3 H11 117(5) 11_455 . ?
C2 C3 H11 152(5) 11_455 . ?
H9 C3 H11 118(6) . . ?
H10 C3 H11 88(5) . . ?
N2 C3 H12 97(2) . . ?
C3 C3 H12 104(2) 11_455 . ?
C2 C3 H12 142(3) 11_455 . ?
H9 C3 H12 148(4) . . ?
H10 C3 H12 121(4) . . ?
H11 C3 H12 33(5) . . ?
C2 C4 N2 59.5(3) 3_556 . ?
C2 C4 C4 89.8(3) 3_556 11_455 ?
N2 C4 C4 110.8(2) . 11_455 ?
C2 C4 H11 143(3) 3_556 . ?
N2 C4 H11 83(3) . . ?
C4 C4 H11 105(3) 11_455 . ?
C2 C4 H12 161(3) 3_556 . ?
N2 C4 H12 107(3) . . ?
C4 C4 H12 108(3) 11_455 . ?
H11 C4 H12 28(4) . . ?
C2 C4 H13 77(5) 3_556 . ?
N2 C4 H13 117(5) . . ?
C4 C4 H13 111(4) 11_455 . ?
H11 C4 H13 126(5) . . ?
H12 C4 H13 101(6) . . ?
C5 O1 Co1 128.5(2) . . ?
C5 O1 H1 109(3) . . ?
Co1 O1 H1 123(3) . . ?
O1 C5 H5 109.0(19) . . ?
O1 C5 H5A 101(3) . . ?
H5 C5 H5A 116(2) . . ?
O1 C5 H5 109.0(19) . 11 ?
H5 C5 H5 106(4) . 11 ?
H5A C5 H5 116(2) . 11 ?
C6 N3 C6 108.7(4) 11 . ?
C6 N3 C7 108.6(2) 11 . ?
C6 N3 C7 108.6(2) . . ?
N3 C6 C6 110.21(16) . 10_557 ?
N3 C6 H6 107(2) . . ?
C6 C6 H6 109.6(19) 10_557 . ?
N3 C6 H6A 109(2) . . ?
C6 C6 H6A 110(2) 10_557 . ?
H6 C6 H6A 111(3) . . ?
N3 C7 C7 110.5(2) . 10_557 ?
N3 C7 H7 109.6 . . ?
C7 C7 H7 109.6 10_557 . ?
N3 C7 H7A 109.6 . . ?
C7 C7 H7A 109.6 10_557 . ?
H7 C7 H7A 108.1 . . ?
N1 Co1 N1 180.0 9_556 . ?
N1 Co1 O1 92.34(11) 9_556 9_556 ?
N1 Co1 O1 87.66(11) . 9_556 ?
N1 Co1 O1 87.66(11) 9_556 . ?
N1 Co1 O1 92.34(11) . . ?
O1 Co1 O1 180.0 9_556 . ?
N1 Co1 N2 90.000(1) 9_556 . ?
N1 Co1 N2 90.0 . . ?
O1 Co1 N2 90.000(1) 9_556 . ?
O1 Co1 N2 90.0 . . ?
N1 Co1 N2 90.0 9_556 9_556 ?
N1 Co1 N2 90.000(1) . 9_556 ?
O1 Co1 N2 90.0 9_556 9_556 ?
O1 Co1 N2 90.000(1) . 9_556 ?
N2 Co1 N2 180.0 . 9_556 ?

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
C3 N2 C2 C4 -156.0(4) . . . 3_556 ?
C3 N2 C2 C4 -22.9(4) 3_556 . . 3_556 ?
C2 N2 C2 C4 -78.2(3) 3_556 . . 3_556 ?
C4 N2 C2 C4 -137.9(4) . . . 3_556 ?
Co1 N2 C2 C4 101.9(3) . . . 3_556 ?
C3 N2 C2 C2 -77.9(3) . . . 11_455 ?
C3 N2 C2 C2 55.3(3) 3_556 . . 11_455 ?
C2 N2 C2 C2 -0.001(3) 3_556 . . 11_455 ?
C4 N2 C2 C2 78.1(3) 3_556 . . 11_455 ?
C4 N2 C2 C2 -59.7(3) . . . 11_455 ?
Co1 N2 C2 C2 179.999(2) . . . 11_455 ?
C3 N2 C2 C3 -44.1(3) . . . 11_455 ?
C3 N2 C2 C3 89.0(4) 3_556 . . 11_455 ?
C2 N2 C2 C3 33.73(19) 3_556 . . 11_455 ?
C4 N2 C2 C3 111.9(4) 3_556 . . 11_455 ?
C4 N2 C2 C3 -26.0(4) . . . 11_455 ?
Co1 N2 C2 C3 -146.27(19) . . . 11_455 ?
C3 N2 C3 C3 -0.004(1) 3_556 . . 11_455 ?
C2 N2 C3 C3 79.2(3) . . . 11_455 ?
C2 N2 C3 C3 -55.7(3) 3_556 . . 11_455 ?
C4 N2 C3 C3 57.9(3) 3_556 . . 11_455 ?
C4 N2 C3 C3 -79.4(3) . . . 11_455 ?
Co1 N2 C3 C3 179.999(1) . . . 11_455 ?
C3 N2 C3 C2 -34.94(19) 3_556 . . 11_455 ?
C2 N2 C3 C2 44.2(4) . . . 11_455 ?
C2 N2 C3 C2 -90.6(4) 3_556 . . 11_455 ?
C4 N2 C3 C2 22.9(4) 3_556 . . 11_455 ?
C4 N2 C3 C2 -114.3(4) . . . 11_455 ?
Co1 N2 C3 C2 145.06(19) . . . 11_455 ?
C3 N2 C4 C2 153.5(4) . . . 3_556 ?
C3 N2 C4 C2 19.8(4) 3_556 . . 3_556 ?
C2 N2 C4 C2 136.0(5) . . . 3_556 ?
C4 N2 C4 C2 76.8(3) 3_556 . . 3_556 ?
Co1 N2 C4 C2 -103.2(3) . . . 3_556 ?
C3 N2 C4 C4 76.7(3) . . . 11_455 ?
C3 N2 C4 C4 -57.0(3) 3_556 . . 11_455 ?
C2 N2 C4 C4 59.2(3) . . . 11_455 ?
C2 N2 C4 C4 -76.8(3) 3_556 . . 11_455 ?
C4 N2 C4 C4 -0.004(1) 3_556 . . 11_455 ?
Co1 N2 C4 C4 179.998(1) . . . 11_455 ?
C6 N3 C6 C6 -59.1(3) 11 . . 10_557 ?
C7 N3 C6 C6 58.9(2) . . . 10_557 ?
C6 N3 C7 C7 59.0(2) 11 . . 10_557 ?
C6 N3 C7 C7 -59.0(2) . . . 10_557 ?

_refine_diff_density_max         1.312
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.089


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
