# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1917387'
_audit_update_record             
;
2019-05-20 deposited with the CCDC.	2020-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            'Cobalt-organic Compound'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 Co0.50 N2 O3 S2'
_chemical_formula_weight         349.84

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           70
_space_group_name_H-M_alt        'F d d d'
_space_group_name_Hall           '-F 2uv 2vw'

_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+3/4, -y+3/4, z'
'-x+3/4, y, -z+3/4'
'x, -y+3/4, -z+3/4'
'x, y+1/2, z+1/2'
'-x+3/4, -y+5/4, z+1/2'
'-x+3/4, y+1/2, -z+5/4'
'x, -y+5/4, -z+5/4'
'x+1/2, y, z+1/2'
'-x+5/4, -y+3/4, z+1/2'
'-x+5/4, y, -z+5/4'
'x+1/2, -y+3/4, -z+5/4'
'x+1/2, y+1/2, z'
'-x+5/4, -y+5/4, z'
'-x+5/4, y+1/2, -z+3/4'
'x+1/2, -y+5/4, -z+3/4'
'-x, -y, -z'
'x-3/4, y-3/4, -z'
'x-3/4, -y, z-3/4'
'-x, y-3/4, z-3/4'
'-x, -y+1/2, -z+1/2'
'x-3/4, y-1/4, -z+1/2'
'x-3/4, -y+1/2, z-1/4'
'-x, y-1/4, z-1/4'
'-x+1/2, -y, -z+1/2'
'x-1/4, y-3/4, -z+1/2'
'x-1/4, -y, z-1/4'
'-x+1/2, y-3/4, z-1/4'
'-x+1/2, -y+1/2, -z'
'x-1/4, y-1/4, -z'
'x-1/4, -y+1/2, z-3/4'
'-x+1/2, y-1/4, z-3/4'

_cell_length_a                   15.4094(13)
_cell_length_b                   16.5616(14)
_cell_length_c                   46.034(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     11748.0(17)
_cell_formula_units_Z            32
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    3271
_cell_measurement_theta_min      1.770
_cell_measurement_theta_max      27.182

_exptl_crystal_description       'Block Shaped'
_exptl_crystal_colour            'Pink Colored'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_F_000             5744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.919
_shelx_estimated_absorpt_T_min   0.898
_shelx_estimated_absorpt_T_max   0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            92123
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_av_R_equivalents  0.1432
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -58
_diffrn_reflns_limit_l_max       58
_diffrn_reflns_theta_min         1.770
_diffrn_reflns_theta_max         27.182
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3271
_reflns_number_gt                2707
_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       'SMART (Bruker, 2000)'
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'Ortep-3 for Windows (Farrugia, 1999) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 2003)'
_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)+(0.0646P)²+104.2606P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3271
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1227
_refine_ls_wR_factor_gt          0.1129
_refine_ls_goodness_of_fit_ref   0.896
_refine_ls_restrained_S_all      0.896
_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
Co01 Co 0.625000 0.625000 0.39886(2) 0.02165(15) Uani 1 2 d S T P . .
S1 S 0.35969(5) 0.43457(4) 0.30412(2) 0.03006(19) Uani 1 1 d . . . . .
S2 S 0.90610(8) 0.42858(6) 0.54132(2) 0.0593(3) Uani 1 1 d . . . . .
O1 O 0.53323(12) 0.71659(12) 0.40081(5) 0.0311(5) Uani 1 1 d . . . . .
O2 O 0.60268(13) 0.81688(13) 0.42318(5) 0.0375(5) Uani 1 1 d . . . . .
O3 O 0.70026(15) 0.68424(15) 0.43121(6) 0.0357(5) Uani 1 1 d . . . . .
N1 N 0.54449(14) 0.56255(14) 0.36691(5) 0.0261(5) Uani 1 1 d . . . . .
C1 C 0.53635(17) 0.78540(16) 0.41261(6) 0.0254(6) Uani 1 1 d . . . . .
C7 C 0.43226(17) 0.47991(16) 0.32944(6) 0.0240(6) Uani 1 1 d . . . . .
C2 C 0.45268(17) 0.83194(16) 0.41409(6) 0.0241(6) Uani 1 1 d . . . . .
C3 C 0.45344(19) 0.91546(17) 0.41499(8) 0.0353(7) Uani 1 1 d . . . . .
H3 H 0.505909 0.943046 0.416078 0.042 Uiso 1 1 calc R U . . .
N2 N 0.7605(3) 0.6041(2) 0.48266(7) 0.0612(9) Uani 1 1 d . . . . .
C4 C 0.3741(2) 0.79197(18) 0.41427(8) 0.0389(8) Uani 1 1 d . . . . .
H4 H 0.373094 0.735829 0.413895 0.047 Uiso 1 1 calc R U . . .
C8 C 0.4204(2) 0.5604(2) 0.33566(9) 0.0490(10) Uani 1 1 d . . . . .
H8 H 0.374570 0.588823 0.327439 0.059 Uiso 1 1 calc R U . . .
C9 C 0.4776(2) 0.5983(2) 0.35426(8) 0.0449(9) Uani 1 1 d . . . . .
H9 H 0.468493 0.652688 0.358180 0.054 Uiso 1 1 calc R U . . .
C5 C 0.5550(2) 0.4850(2) 0.36041(9) 0.0474(9) Uani 1 1 d . . . . .
H5 H 0.602051 0.458001 0.368557 0.057 Uiso 1 1 calc R U . . .
C6 C 0.5005(2) 0.44178(19) 0.34228(9) 0.0469(9) Uani 1 1 d . . . . .
H6 H 0.510336 0.387187 0.338900 0.056 Uiso 1 1 calc R U . . .
C12 C 0.8466(2) 0.4929(2) 0.51755(7) 0.0432(8) Uani 1 1 d . . . . .
C10 C 0.7470(3) 0.5253(3) 0.48065(10) 0.0675(13) Uani 1 1 d . . . . .
H10 H 0.706173 0.507636 0.467202 0.081 Uiso 1 1 calc R U . . .
C13 C 0.8584(3) 0.5745(2) 0.52136(9) 0.0578(11) Uani 1 1 d . . . . .
H13 H 0.895057 0.593756 0.535827 0.069 Uiso 1 1 calc R U . . .
C11 C 0.7888(3) 0.4678(3) 0.49696(10) 0.0645(12) Uani 1 1 d . . . . .
H11 H 0.778011 0.413184 0.494055 0.077 Uiso 1 1 calc R U . . .
C14 C 0.8148(3) 0.6275(3) 0.50336(10) 0.0636(12) Uani 1 1 d . . . . .
H14 H 0.824126 0.682582 0.505882 0.076 Uiso 1 1 calc R U . . .
H3B H 0.681(3) 0.730(3) 0.4317(9) 0.052(12) Uiso 1 1 d . . . . .
H3A H 0.709(3) 0.666(3) 0.4463(10) 0.061(15) Uiso 1 1 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
Co01 O1 2.0758(18) . ?
Co01 O1 2.0759(19) 14 ?
Co01 O3 2.127(2) . ?
Co01 O3 2.127(2) 14 ?
Co01 N1 2.185(2) . ?
Co01 N1 2.185(2) 14 ?
S1 C7 1.781(3) . ?
S1 S1 2.0287(14) 2 ?
S2 C12 1.781(4) . ?
S2 S2 2.017(2) 2_655 ?
O1 C1 1.263(3) . ?
O2 C1 1.246(3) . ?
O3 H3B 0.82(5) . ?
O3 H3A 0.77(5) . ?
N1 C9 1.323(4) . ?
N1 C5 1.329(4) . ?
C1 C2 1.504(4) . ?
C7 C6 1.361(4) . ?
C7 C8 1.375(4) . ?
C2 C4 1.380(4) . ?
C2 C3 1.384(4) . ?
C3 C4 1.388(4) 2_565 ?
C3 H3 0.9300 . ?
N2 C14 1.326(5) . ?
N2 C10 1.325(6) . ?
C4 H4 0.9300 . ?
C8 C9 1.379(5) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C5 C6 1.383(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C12 C11 1.365(5) . ?
C12 C13 1.376(5) . ?
C10 C11 1.373(6) . ?
C10 H10 0.9300 . ?
C13 C14 1.381(6) . ?
C13 H13 0.9300 . ?
C11 H11 0.9300 . ?
C14 H14 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 Co01 O1 175.04(12) . 14 ?
O1 Co01 O3 90.23(9) . . ?
O1 Co01 O3 86.29(9) 14 . ?
O1 Co01 O3 86.30(9) . 14 ?
O1 Co01 O3 90.23(9) 14 14 ?
O3 Co01 O3 91.15(15) . 14 ?
O1 Co01 N1 89.33(8) . . ?
O1 Co01 N1 94.02(9) 14 . ?
O3 Co01 N1 177.88(10) . . ?
O3 Co01 N1 86.76(10) 14 . ?
O1 Co01 N1 94.01(9) . 14 ?
O1 Co01 N1 89.33(8) 14 14 ?
O3 Co01 N1 86.76(10) . 14 ?
O3 Co01 N1 177.88(10) 14 14 ?
N1 Co01 N1 95.34(13) . 14 ?
C7 S1 S1 105.31(10) . 2 ?
C12 S2 S2 106.35(14) . 2_655 ?
C1 O1 Co01 130.68(18) . . ?
Co01 O3 H3B 105(3) . . ?
Co01 O3 H3A 123(3) . . ?
H3B O3 H3A 114(4) . . ?
C9 N1 C5 115.4(3) . . ?
C9 N1 Co01 121.8(2) . . ?
C5 N1 Co01 122.7(2) . . ?
O2 C1 O1 125.2(2) . . ?
O2 C1 C2 118.1(2) . . ?
O1 C1 C2 116.7(2) . . ?
C6 C7 C8 117.5(3) . . ?
C6 C7 S1 125.0(2) . . ?
C8 C7 S1 117.5(2) . . ?
C4 C2 C3 119.1(3) . . ?
C4 C2 C1 120.4(2) . . ?
C3 C2 C1 120.4(3) . . ?
C2 C3 C4 120.0(3) . 2_565 ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 2_565 . ?
C14 N2 C10 115.9(4) . . ?
C2 C4 C3 120.8(3) . 2_565 ?
C2 C4 H4 119.6 . . ?
C3 C4 H4 119.6 2_565 . ?
C7 C8 C9 119.1(3) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
N1 C9 C8 124.5(3) . . ?
N1 C9 H9 117.7 . . ?
C8 C9 H9 117.7 . . ?
N1 C5 C6 124.1(3) . . ?
N1 C5 H5 117.9 . . ?
C6 C5 H5 117.9 . . ?
C7 C6 C5 119.4(3) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C11 C12 C13 118.2(4) . . ?
C11 C12 S2 125.5(3) . . ?
C13 C12 S2 116.2(3) . . ?
N2 C10 C11 124.8(4) . . ?
N2 C10 H10 117.6 . . ?
C11 C10 H10 117.6 . . ?
C12 C13 C14 119.0(4) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C12 C11 C10 118.4(4) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
N2 C14 C13 123.5(4) . . ?
N2 C14 H14 118.3 . . ?
C13 C14 H14 118.3 . . ?

_refine_diff_density_max         0.427
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.065

