# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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 
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data_shelx
_audit_block_doi                 10.5517/ccdc.csd.cc20vqrc
_database_code_depnum_ccdc_archive 'CCDC 1872733'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.poly.2018.12.039 2018
loop_
_audit_author_name
_audit_author_address
'Hannachi Anissa'
;FSB
Tunisia
;
_audit_update_record             
;
2018-10-11 deposited with the CCDC.	2024-03-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H24 Co N10 S2'
_chemical_formula_sum            'C18 H24 Co N10 S2'
_chemical_formula_weight         503.52

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'
S S 0.1246 0.1234 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2, y+1/2, z'
'-x+1/2, y+1/2, -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'

_cell_length_a                   24.6697(19)
_cell_length_b                   13.3392(10)
_cell_length_c                   15.2344(9)
_cell_angle_alpha                90
_cell_angle_beta                 115.878(4)
_cell_angle_gamma                90
_cell_volume                     4510.5(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    4721
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      27.878

_exptl_crystal_description       prism
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_F_000             2088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.974
_shelx_estimated_absorpt_T_min   0.786
_shelx_estimated_absorpt_T_max   0.876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6291
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Sadabs (Bruker, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD with APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            8370
_diffrn_reflns_av_unetI/netI     0.1014
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.781
_diffrn_reflns_theta_max         28.343
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5554
_reflns_number_gt                3494
_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_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Bruker, 2008)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    SHELXL-2016/6
_computing_publication_material  SHELXL-2016/6
_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)+(0.0001P)²+11.0786P] 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         5554
_refine_ls_number_parameters     286
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1149
_refine_ls_R_factor_gt           0.0615
_refine_ls_wR_factor_ref         0.1111
_refine_ls_wR_factor_gt          0.0966
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.26143(2) 0.51422(3) 0.34466(3) 0.02566(13) Uani 1 1 d . . . . .
S1 S 0.25996(5) 0.37172(7) 0.62851(7) 0.0367(3) Uani 1 1 d . . . . .
S2 S 0.25288(4) 0.85620(6) 0.40693(6) 0.0277(2) Uani 1 1 d . . . . .
N1 N 0.33188(13) 0.4586(2) 0.3239(2) 0.0233(6) Uani 1 1 d D . . . .
H1 H 0.3171(14) 0.458(3) 0.2592(13) 0.028 Uiso 1 1 d D U . . .
N4 N 0.44903(13) 0.3741(2) 0.3724(2) 0.0291(7) Uani 1 1 d . . . . .
N8 N 0.54739(14) 0.3940(3) 0.3925(2) 0.0368(8) Uani 1 1 d . . . . .
N12 N 0.50382(14) 0.2304(2) 0.3799(2) 0.0369(8) Uani 1 1 d . . . . .
N13 N 0.26521(15) 0.4521(2) 0.4634(2) 0.0343(8) Uani 1 1 d . . . . .
N15 N 0.26103(14) 0.6595(2) 0.3525(2) 0.0310(7) Uani 1 1 d . . . . .
N1A N 0.18316(13) 0.4651(2) 0.2336(2) 0.0260(7) Uani 1 1 d D . . . .
H1A H 0.1907(15) 0.466(3) 0.1805(18) 0.031 Uiso 1 1 d D U . . .
N4A N 0.06311(14) 0.3843(2) 0.1571(2) 0.0356(8) Uani 1 1 d . . . . .
N8A N 0.00270(14) 0.2457(2) 0.1390(2) 0.0360(8) Uani 1 1 d . . . . .
N12A N -0.03921(15) 0.4114(3) 0.1019(2) 0.0390(8) Uani 1 1 d . . . . .
C2 C 0.38697(16) 0.5208(3) 0.3632(3) 0.0325(8) Uani 1 1 d . . . . .
H2A H 0.402202 0.526263 0.434819 0.039 Uiso 1 1 calc R U . . .
H2B H 0.376795 0.589084 0.335393 0.039 Uiso 1 1 calc R U . . .
C3 C 0.43596(17) 0.4781(3) 0.3402(3) 0.0358(9) Uani 1 1 d . . . . .
H3A H 0.423173 0.481712 0.268955 0.043 Uiso 1 1 calc R U . . .
H3B H 0.472972 0.518856 0.372964 0.043 Uiso 1 1 calc R U . . .
C5 C 0.39682(16) 0.3082(3) 0.3428(3) 0.0299(8) Uani 1 1 d . . . . .
H5A H 0.409230 0.243610 0.378100 0.036 Uiso 1 1 calc R U . . .
H5B H 0.380489 0.294229 0.272054 0.036 Uiso 1 1 calc R U . . .
C6 C 0.34841(16) 0.3561(3) 0.3648(3) 0.0278(8) Uani 1 1 d . . . . .
H6A H 0.312005 0.313245 0.337759 0.033 Uiso 1 1 calc R U . . .
H6B H 0.362733 0.359192 0.436368 0.033 Uiso 1 1 calc R U . . .
C7 C 0.50241(16) 0.3315(3) 0.3822(2) 0.0304(9) Uani 1 1 d . . . . .
C9 C 0.59868(18) 0.3500(3) 0.4043(3) 0.0400(10) Uani 1 1 d . . . . .
H9 H 0.632064 0.391386 0.413511 0.048 Uiso 1 1 calc R U . . .
C10 C 0.60575(18) 0.2480(3) 0.4039(3) 0.0394(10) Uani 1 1 d . . . . .
H10 H 0.642659 0.218452 0.411875 0.047 Uiso 1 1 calc R U . . .
C11 C 0.55646(18) 0.1909(3) 0.3913(3) 0.0404(10) Uani 1 1 d . . . . .
H11 H 0.559880 0.119990 0.390555 0.049 Uiso 1 1 calc R U . . .
C14 C 0.26320(16) 0.4181(2) 0.5323(3) 0.0271(8) Uani 1 1 d . . . . .
C16 C 0.25713(15) 0.7410(3) 0.3753(2) 0.0240(8) Uani 1 1 d . . . . .
C2A C 0.17086(16) 0.3596(2) 0.2514(2) 0.0272(8) Uani 1 1 d . . . . .
H2A1 H 0.168616 0.356071 0.314649 0.033 Uiso 1 1 calc R U . . .
H2A2 H 0.204882 0.316857 0.256320 0.033 Uiso 1 1 calc R U . . .
C3A C 0.11331(16) 0.3185(3) 0.1727(3) 0.0349(9) Uani 1 1 d . . . . .
H3A1 H 0.117512 0.311902 0.111195 0.042 Uiso 1 1 calc R U . . .
H3A2 H 0.105429 0.251104 0.191678 0.042 Uiso 1 1 calc R U . . .
C5A C 0.07253(18) 0.4882(3) 0.1364(3) 0.0438(10) Uani 1 1 d . . . . .
H5A1 H 0.038234 0.529985 0.131846 0.053 Uiso 1 1 calc R U . . .
H5A2 H 0.074712 0.491790 0.073122 0.053 Uiso 1 1 calc R U . . .
C6A C 0.13025(17) 0.5274(3) 0.2165(3) 0.0371(9) Uani 1 1 d . . . . .
H6A1 H 0.137438 0.596200 0.199452 0.045 Uiso 1 1 calc R U . . .
H6A2 H 0.125548 0.531507 0.277694 0.045 Uiso 1 1 calc R U . . .
C7A C 0.00679(17) 0.3461(3) 0.1317(3) 0.0328(9) Uani 1 1 d . . . . .
C9A C -0.05189(19) 0.2118(3) 0.1193(3) 0.0430(11) Uani 1 1 d . . . . .
H9A H -0.056583 0.141863 0.125681 0.052 Uiso 1 1 calc R U . . .
C10A C -0.1022(2) 0.2716(3) 0.0901(3) 0.0439(11) Uani 1 1 d . . . . .
H10A H -0.140691 0.245186 0.077086 0.053 Uiso 1 1 calc R U . . .
C11A C -0.09309(18) 0.3721(4) 0.0809(3) 0.0442(11) Uani 1 1 d . . . . .
H11A H -0.126955 0.415629 0.058597 0.053 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 N15 1.941(3) . ?
Co1 N13 1.955(3) . ?
Co1 N1 2.037(3) . ?
Co1 N1A 2.042(3) . ?
S1 C14 1.625(4) . ?
S2 C16 1.627(4) . ?
N1 C2 1.478(4) . ?
N1 C6 1.483(4) . ?
N1 H1 0.890(17) . ?
N4 C7 1.381(4) . ?
N4 C5 1.459(4) . ?
N4 C3 1.461(5) . ?
N8 C9 1.334(5) . ?
N8 C7 1.342(5) . ?
N12 C11 1.341(5) . ?
N12 C7 1.350(5) . ?
N13 C14 1.164(4) . ?
N15 C16 1.159(4) . ?
N1A C6A 1.472(4) . ?
N1A C2A 1.489(4) . ?
N1A H1A 0.906(17) . ?
N4A C7A 1.367(5) . ?
N4A C3A 1.450(5) . ?
N4A C5A 1.463(5) . ?
N8A C9A 1.325(5) . ?
N8A C7A 1.352(5) . ?
N12A C11A 1.332(5) . ?
N12A C7A 1.343(5) . ?
C2 C3 1.509(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 C6 1.515(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C9 C10 1.372(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.375(6) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C2A C3A 1.506(5) . ?
C2A H2A1 0.9900 . ?
C2A H2A2 0.9900 . ?
C3A H3A1 0.9900 . ?
C3A H3A2 0.9900 . ?
C5A C6A 1.508(5) . ?
C5A H5A1 0.9900 . ?
C5A H5A2 0.9900 . ?
C6A H6A1 0.9900 . ?
C6A H6A2 0.9900 . ?
C9A C10A 1.375(6) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.377(6) . ?
C10A H10A 0.9500 . ?
C11A H11A 0.9500 . ?

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
N15 Co1 N13 111.44(12) . . ?
N15 Co1 N1 113.63(12) . . ?
N13 Co1 N1 106.83(12) . . ?
N15 Co1 N1A 110.06(12) . . ?
N13 Co1 N1A 106.06(12) . . ?
N1 Co1 N1A 108.47(11) . . ?
C2 N1 C6 108.2(3) . . ?
C2 N1 Co1 115.4(2) . . ?
C6 N1 Co1 111.6(2) . . ?
C2 N1 H1 108(2) . . ?
C6 N1 H1 111(2) . . ?
Co1 N1 H1 102(2) . . ?
C7 N4 C5 117.2(3) . . ?
C7 N4 C3 119.2(3) . . ?
C5 N4 C3 115.7(3) . . ?
C9 N8 C7 115.4(4) . . ?
C11 N12 C7 115.1(4) . . ?
C14 N13 Co1 174.9(3) . . ?
C16 N15 Co1 163.5(3) . . ?
C6A N1A C2A 109.3(3) . . ?
C6A N1A Co1 114.2(2) . . ?
C2A N1A Co1 110.3(2) . . ?
C6A N1A H1A 110(2) . . ?
C2A N1A H1A 109(2) . . ?
Co1 N1A H1A 104(2) . . ?
C7A N4A C3A 120.7(3) . . ?
C7A N4A C5A 121.9(3) . . ?
C3A N4A C5A 113.8(3) . . ?
C9A N8A C7A 115.1(4) . . ?
C11A N12A C7A 115.7(4) . . ?
N1 C2 C3 112.5(3) . . ?
N1 C2 H2A 109.1 . . ?
C3 C2 H2A 109.1 . . ?
N1 C2 H2B 109.1 . . ?
C3 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
N4 C3 C2 111.2(3) . . ?
N4 C3 H3A 109.4 . . ?
C2 C3 H3A 109.4 . . ?
N4 C3 H3B 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
N4 C5 C6 110.6(3) . . ?
N4 C5 H5A 109.5 . . ?
C6 C5 H5A 109.5 . . ?
N4 C5 H5B 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
N1 C6 C5 113.3(3) . . ?
N1 C6 H6A 108.9 . . ?
C5 C6 H6A 108.9 . . ?
N1 C6 H6B 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
N8 C7 N12 126.5(3) . . ?
N8 C7 N4 117.2(3) . . ?
N12 C7 N4 116.3(3) . . ?
N8 C9 C10 123.5(4) . . ?
N8 C9 H9 118.3 . . ?
C10 C9 H9 118.3 . . ?
C9 C10 C11 116.3(4) . . ?
C9 C10 H10 121.8 . . ?
C11 C10 H10 121.8 . . ?
N12 C11 C10 123.2(4) . . ?
N12 C11 H11 118.4 . . ?
C10 C11 H11 118.4 . . ?
N13 C14 S1 179.4(4) . . ?
N15 C16 S2 178.8(3) . . ?
N1A C2A C3A 113.2(3) . . ?
N1A C2A H2A1 108.9 . . ?
C3A C2A H2A1 108.9 . . ?
N1A C2A H2A2 108.9 . . ?
C3A C2A H2A2 108.9 . . ?
H2A1 C2A H2A2 107.7 . . ?
N4A C3A C2A 110.6(3) . . ?
N4A C3A H3A1 109.5 . . ?
C2A C3A H3A1 109.5 . . ?
N4A C3A H3A2 109.5 . . ?
C2A C3A H3A2 109.5 . . ?
H3A1 C3A H3A2 108.1 . . ?
N4A C5A C6A 109.7(3) . . ?
N4A C5A H5A1 109.7 . . ?
C6A C5A H5A1 109.7 . . ?
N4A C5A H5A2 109.7 . . ?
C6A C5A H5A2 109.7 . . ?
H5A1 C5A H5A2 108.2 . . ?
N1A C6A C5A 113.5(3) . . ?
N1A C6A H6A1 108.9 . . ?
C5A C6A H6A1 108.9 . . ?
N1A C6A H6A2 108.9 . . ?
C5A C6A H6A2 108.9 . . ?
H6A1 C6A H6A2 107.7 . . ?
N12A C7A N8A 126.1(4) . . ?
N12A C7A N4A 117.3(4) . . ?
N8A C7A N4A 116.6(3) . . ?
N8A C9A C10A 124.0(4) . . ?
N8A C9A H9A 118.0 . . ?
C10A C9A H9A 118.0 . . ?
C9A C10A C11A 115.7(4) . . ?
C9A C10A H10A 122.1 . . ?
C11A C10A H10A 122.1 . . ?
N12A C11A C10A 123.3(4) . . ?
N12A C11A H11A 118.4 . . ?
C10A C11A H11A 118.4 . . ?

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
C6 N1 C2 C3 57.6(4) . . . . ?
Co1 N1 C2 C3 -176.7(2) . . . . ?
C7 N4 C3 C2 -162.4(3) . . . . ?
C5 N4 C3 C2 49.4(4) . . . . ?
N1 C2 C3 N4 -53.9(4) . . . . ?
C7 N4 C5 C6 162.7(3) . . . . ?
C3 N4 C5 C6 -48.5(4) . . . . ?
C2 N1 C6 C5 -57.3(4) . . . . ?
Co1 N1 C6 C5 174.7(2) . . . . ?
N4 C5 C6 N1 52.7(4) . . . . ?
C9 N8 C7 N12 -2.1(5) . . . . ?
C9 N8 C7 N4 178.3(3) . . . . ?
C11 N12 C7 N8 1.6(5) . . . . ?
C11 N12 C7 N4 -178.9(3) . . . . ?
C5 N4 C7 N8 168.6(3) . . . . ?
C3 N4 C7 N8 21.0(5) . . . . ?
C5 N4 C7 N12 -11.0(5) . . . . ?
C3 N4 C7 N12 -158.6(3) . . . . ?
C7 N8 C9 C10 1.6(5) . . . . ?
N8 C9 C10 C11 -0.6(6) . . . . ?
C7 N12 C11 C10 -0.4(5) . . . . ?
C9 C10 C11 N12 0.0(6) . . . . ?
C6A N1A C2A C3A 53.1(4) . . . . ?
Co1 N1A C2A C3A 179.4(2) . . . . ?
C7A N4A C3A C2A -146.3(3) . . . . ?
C5A N4A C3A C2A 54.5(4) . . . . ?
N1A C2A C3A N4A -53.5(4) . . . . ?
C7A N4A C5A C6A 146.2(3) . . . . ?
C3A N4A C5A C6A -54.9(4) . . . . ?
C2A N1A C6A C5A -54.1(4) . . . . ?
Co1 N1A C6A C5A -178.1(2) . . . . ?
N4A C5A C6A N1A 54.9(4) . . . . ?
C11A N12A C7A N8A 2.3(5) . . . . ?
C11A N12A C7A N4A -177.8(3) . . . . ?
C9A N8A C7A N12A -3.8(5) . . . . ?
C9A N8A C7A N4A 176.3(3) . . . . ?
C3A N4A C7A N12A -168.5(3) . . . . ?
C5A N4A C7A N12A -11.0(5) . . . . ?
C3A N4A C7A N8A 11.4(5) . . . . ?
C5A N4A C7A N8A 168.9(3) . . . . ?
C7A N8A C9A C10A 2.2(5) . . . . ?
N8A C9A C10A C11A 0.6(6) . . . . ?
C7A N12A C11A C10A 0.9(5) . . . . ?
C9A C10A C11A N12A -2.3(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 S1 0.890(17) 2.95(3) 3.539(3) 126(3) 6_565
N1 H1 S2 0.890(17) 2.72(2) 3.491(3) 146(3) 4_545
N1A H1A S2 0.906(17) 2.74(3) 3.483(3) 140(3) 4_545

_refine_diff_density_max         0.395
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.093
####################################################################### 
# 
# 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_CCDC1
_audit_block_doi                 10.5517/ccdc.csd.cc20vqwh
_database_code_depnum_ccdc_archive 'CCDC 1872737'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.poly.2018.12.039 2018
loop_
_audit_author_name
_audit_author_address
'Hannachi Anissa'
;FSB
Tunisia
;
_audit_update_record             
;
2018-10-11 deposited with the CCDC.	2024-03-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 Co N4 S4, C8 H14 N4, H2 O'
_chemical_formula_sum            'C12 H16 Co N8 O S4'
_chemical_formula_weight         475.50

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'
S S 0.1246 0.1234 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   16.4142(3)
_cell_length_b                   16.5691(4)
_cell_length_c                   15.1392(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4117.39(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    5372
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      27.878

_exptl_crystal_description       prism
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_F_000             1944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.258
_shelx_estimated_absorpt_T_min   0.805
_shelx_estimated_absorpt_T_max   0.864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5999
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Sadabs (Bruker, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD with APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            31443
_diffrn_reflns_av_unetI/netI     0.0749
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.746
_diffrn_reflns_theta_max         28.357
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9334
_reflns_number_gt                6841
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.928
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.999

_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_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Bruker, 2008)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    SHELXL-2016/6
_computing_publication_material  SHELXL-2016/6
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+3.4804P] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.073(19)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         9334
_refine_ls_number_parameters     500
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.0859
_refine_ls_wR_factor_gt          0.0778
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 0.62506(4) 0.79964(4) 0.44170(6) 0.02854(17) Uani 1 1 d . . . . .
S1 S 0.48752(10) 0.94463(11) 0.66661(13) 0.0492(5) Uani 1 1 d . . . . .
S2 S 0.53768(10) 0.80052(10) 0.14569(11) 0.0440(4) Uani 1 1 d . . . . .
S3 S 0.90558(8) 0.78673(9) 0.39255(11) 0.0336(3) Uani 1 1 d . . . . .
S4 S 0.59631(12) 0.51920(11) 0.50131(16) 0.0624(6) Uani 1 1 d . . . . .
N13 N 0.5691(3) 0.8600(3) 0.5346(3) 0.0337(12) Uani 1 1 d . . . . .
N15 N 0.5803(3) 0.8193(3) 0.3237(3) 0.0322(12) Uani 1 1 d . . . . .
N17 N 0.7429(3) 0.8172(3) 0.4374(4) 0.0341(11) Uani 1 1 d . . . . .
N19 N 0.6108(3) 0.6839(3) 0.4641(4) 0.0403(15) Uani 1 1 d . . . . .
C14 C 0.5361(3) 0.8959(3) 0.5895(4) 0.0266(12) Uani 1 1 d . . . . .
C16 C 0.5626(3) 0.8126(3) 0.2496(4) 0.0290(13) Uani 1 1 d . . . . .
C18 C 0.8107(3) 0.8055(3) 0.4191(4) 0.0284(13) Uani 1 1 d . . . . .
C20 C 0.6044(3) 0.6149(4) 0.4783(5) 0.0399(16) Uani 1 1 d . . . . .
Co1A Co 0.60991(4) 0.29417(5) 0.43995(7) 0.03165(18) Uani 1 1 d . . . . .
S1A S 0.32424(7) 0.29050(9) 0.43609(13) 0.0370(3) Uani 1 1 d . . . . .
S2A S 0.79872(8) 0.38706(9) 0.23237(10) 0.0339(3) Uani 1 1 d . . . . .
S3A S 0.73559(11) 0.36269(10) 0.71022(12) 0.0478(5) Uani 1 1 d . . . . .
S4A S 0.63311(9) 0.01452(10) 0.38302(14) 0.0454(4) Uani 1 1 d . . . . .
N13A N 0.4926(2) 0.3129(3) 0.4422(4) 0.0385(11) Uani 1 1 d . . . . .
N15A N 0.6693(3) 0.3487(3) 0.3447(4) 0.0376(13) Uani 1 1 d . . . . .
N17A N 0.6576(3) 0.3244(3) 0.5528(4) 0.0375(13) Uani 1 1 d . . . . .
N19A N 0.6220(3) 0.1781(3) 0.4211(4) 0.0433(16) Uani 1 1 d . . . . .
C14A C 0.4229(3) 0.3029(3) 0.4401(4) 0.0273(11) Uani 1 1 d . . . . .
C16A C 0.7230(3) 0.3648(3) 0.2985(4) 0.0294(13) Uani 1 1 d . . . . .
C18A C 0.6885(3) 0.3404(3) 0.6181(4) 0.0303(13) Uani 1 1 d . . . . .
C20A C 0.6265(3) 0.1110(4) 0.4058(4) 0.0326(15) Uani 1 1 d . . . . .
N4 N 0.8262(3) 0.5297(3) 0.4986(3) 0.0261(10) Uani 1 1 d . . . . .
N1 N 0.9344(3) 0.4594(3) 0.3750(3) 0.0265(10) Uani 1 1 d D . . . .
H1A H 0.901(3) 0.432(3) 0.339(3) 0.032 Uiso 1 1 d D U . . .
H1B H 0.9879(17) 0.453(3) 0.361(4) 0.032 Uiso 1 1 d D U . . .
N8 N 0.7976(3) 0.6555(3) 0.5553(3) 0.0289(11) Uani 1 1 d . . . . .
N12 N 0.7768(3) 0.5411(3) 0.6430(3) 0.0273(11) Uani 1 1 d D . . . .
H12 H 0.774(3) 0.4881(16) 0.651(4) 0.033 Uiso 1 1 d D U . . .
C2 C 0.9252(3) 0.4245(3) 0.4649(4) 0.0266(13) Uani 1 1 d . . . . .
H2A H 0.967478 0.447140 0.504342 0.032 Uiso 1 1 calc R U . . .
H2B H 0.933004 0.365314 0.462078 0.032 Uiso 1 1 calc R U . . .
C3 C 0.8416(3) 0.4429(3) 0.5022(4) 0.0287(13) Uani 1 1 d . . . . .
H3A H 0.799523 0.413978 0.467728 0.034 Uiso 1 1 calc R U . . .
H3B H 0.838507 0.424128 0.564216 0.034 Uiso 1 1 calc R U . . .
C5 C 0.8339(3) 0.5638(3) 0.4102(4) 0.0290(13) Uani 1 1 d . . . . .
H5A H 0.824420 0.622723 0.412678 0.035 Uiso 1 1 calc R U . . .
H5B H 0.791977 0.539788 0.371121 0.035 Uiso 1 1 calc R U . . .
C6 C 0.9174(3) 0.5474(3) 0.3725(4) 0.0296(13) Uani 1 1 d . . . . .
H6A H 0.919999 0.567053 0.310841 0.036 Uiso 1 1 calc R U . . .
H6B H 0.958958 0.576706 0.407422 0.036 Uiso 1 1 calc R U . . .
C7 C 0.8005(3) 0.5753(3) 0.5662(4) 0.0245(12) Uani 1 1 d . . . . .
C9 C 0.7740(3) 0.6992(4) 0.6234(4) 0.0345(14) Uani 1 1 d . . . . .
H9 H 0.772041 0.756163 0.616270 0.041 Uiso 1 1 calc R U . . .
C10 C 0.7516(4) 0.6675(3) 0.7050(4) 0.0365(14) Uani 1 1 d . . . . .
H10 H 0.736243 0.701287 0.752897 0.044 Uiso 1 1 calc R U . . .
C11 C 0.7530(3) 0.5867(3) 0.7126(4) 0.0313(13) Uani 1 1 d . . . . .
H11 H 0.737295 0.561725 0.766470 0.038 Uiso 1 1 calc R U . . .
N4A N 0.8969(3) 0.0038(3) 0.6469(4) 0.0367(12) Uani 1 1 d . . . . .
N1A N 0.7886(3) 0.1378(3) 0.6397(4) 0.0402(13) Uani 1 1 d D . . . .
H1C H 0.811(4) 0.171(3) 0.599(3) 0.048 Uiso 1 1 d D U . . .
H1D H 0.740(2) 0.159(3) 0.655(4) 0.048 Uiso 1 1 d D U . . .
N8A N 0.9179(3) -0.1298(3) 0.6106(3) 0.0350(12) Uani 1 1 d . . . . .
N12A N 0.9973(3) -0.0694(3) 0.7217(3) 0.0302(11) Uani 1 1 d D . . . .
H12A H 1.009(3) -0.032(3) 0.760(3) 0.036 Uiso 1 1 d D U . . .
C2A C 0.8428(4) 0.1252(4) 0.7162(5) 0.0429(16) Uani 1 1 d . . . . .
H2C H 0.813809 0.093732 0.762061 0.051 Uiso 1 1 calc R U . . .
H2D H 0.857959 0.178064 0.741919 0.051 Uiso 1 1 calc R U . . .
C3A C 0.9188(4) 0.0805(3) 0.6880(5) 0.0465(18) Uani 1 1 d . . . . .
H3C H 0.949961 0.113849 0.645479 0.056 Uiso 1 1 calc R U . . .
H3D H 0.953851 0.070494 0.740077 0.056 Uiso 1 1 calc R U . . .
C5A C 0.8422(4) 0.0132(4) 0.5717(4) 0.0440(16) Uani 1 1 d . . . . .
H5C H 0.826545 -0.040764 0.549287 0.053 Uiso 1 1 calc R U . . .
H5D H 0.870927 0.042086 0.523717 0.053 Uiso 1 1 calc R U . . .
C6A C 0.7669(4) 0.0592(3) 0.5965(5) 0.0426(16) Uani 1 1 d . . . . .
H6C H 0.733561 0.026407 0.637589 0.051 Uiso 1 1 calc R U . . .
H6D H 0.733961 0.069668 0.542915 0.051 Uiso 1 1 calc R U . . .
C7A C 0.9378(3) -0.0653(3) 0.6598(4) 0.0300(13) Uani 1 1 d . . . . .
C9A C 0.9598(3) -0.1970(3) 0.6235(4) 0.0350(15) Uani 1 1 d . . . . .
H9A H 0.946376 -0.242888 0.588826 0.042 Uiso 1 1 calc R U . . .
C10A C 1.0223(3) -0.2042(4) 0.6846(4) 0.0380(15) Uani 1 1 d . . . . .
H10A H 1.051967 -0.253077 0.691186 0.046 Uiso 1 1 calc R U . . .
C11A C 1.0389(3) -0.1385(4) 0.7346(4) 0.0337(14) Uani 1 1 d . . . . .
H11A H 1.079978 -0.141038 0.778727 0.040 Uiso 1 1 calc R U . . .
O1 O 0.6461(3) 0.1729(2) 0.7191(3) 0.0386(10) Uani 1 1 d D . . . .
H1O H 0.642(4) 0.207(3) 0.759(3) 0.058 Uiso 1 1 d D U . . .
H1P H 0.605(3) 0.172(4) 0.687(4) 0.058 Uiso 1 1 d D U . . .
O2 O 1.0545(3) 0.0225(3) 0.8540(4) 0.0627(14) Uani 1 1 d D . . . .
H2O H 1.073(5) 0.0701(18) 0.850(5) 0.094 Uiso 1 1 d D U . . .
H2P H 1.019(4) 0.020(5) 0.895(4) 0.094 Uiso 1 1 d D 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 N13 1.955(5) . ?
Co1 N17 1.958(4) . ?
Co1 N15 1.959(5) . ?
Co1 N19 1.961(5) . ?
S1 C14 1.628(6) . ?
S2 C16 1.638(7) . ?
S3 C18 1.638(6) . ?
S4 C20 1.630(7) . ?
N13 C14 1.157(7) . ?
N15 C16 1.164(7) . ?
N17 C18 1.163(6) . ?
N19 C20 1.167(7) . ?
Co1A N17A 1.944(6) . ?
Co1A N13A 1.951(4) . ?
Co1A N19A 1.955(6) . ?
Co1A N15A 1.961(5) . ?
S1A C14A 1.633(5) . ?
S2A C16A 1.638(6) . ?
S3A C18A 1.637(7) . ?
S4A C20A 1.639(7) . ?
N13A C14A 1.156(6) . ?
N15A C16A 1.157(7) . ?
N17A C18A 1.142(7) . ?
N19A C20A 1.138(7) . ?
N4 C7 1.339(7) . ?
N4 C5 1.458(7) . ?
N4 C3 1.461(6) . ?
N1 C6 1.485(7) . ?
N1 C2 1.486(7) . ?
N1 H1A 0.89(2) . ?
N1 H1B 0.91(2) . ?
N8 C9 1.318(7) . ?
N8 C7 1.341(6) . ?
N12 C7 1.351(7) . ?
N12 C11 1.355(7) . ?
N12 H12 0.89(2) . ?
C2 C3 1.515(7) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 C6 1.509(7) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C9 C10 1.392(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.344(8) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
N4A C7A 1.342(6) . ?
N4A C5A 1.459(8) . ?
N4A C3A 1.460(7) . ?
N1A C2A 1.476(8) . ?
N1A C6A 1.501(8) . ?
N1A H1C 0.91(3) . ?
N1A H1D 0.90(3) . ?
N8A C9A 1.322(7) . ?
N8A C7A 1.342(7) . ?
N12A C11A 1.347(7) . ?
N12A C7A 1.355(7) . ?
N12A H12A 0.87(3) . ?
C2A C3A 1.514(8) . ?
C2A H2C 0.9900 . ?
C2A H2D 0.9900 . ?
C3A H3C 0.9900 . ?
C3A H3D 0.9900 . ?
C5A C6A 1.500(8) . ?
C5A H5C 0.9900 . ?
C5A H5D 0.9900 . ?
C6A H6C 0.9900 . ?
C6A H6D 0.9900 . ?
C9A C10A 1.386(8) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.355(8) . ?
C10A H10A 0.9500 . ?
C11A H11A 0.9500 . ?
O1 H1O 0.84(3) . ?
O1 H1P 0.83(3) . ?
O2 H2O 0.85(2) . ?
O2 H2P 0.85(2) . ?

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
N13 Co1 N17 114.3(2) . . ?
N13 Co1 N15 113.2(2) . . ?
N17 Co1 N15 108.4(2) . . ?
N13 Co1 N19 108.7(2) . . ?
N17 Co1 N19 105.59(19) . . ?
N15 Co1 N19 106.0(2) . . ?
C14 N13 Co1 179.8(6) . . ?
C16 N15 Co1 163.0(5) . . ?
C18 N17 Co1 158.2(5) . . ?
C20 N19 Co1 178.2(5) . . ?
N13 C14 S1 178.4(5) . . ?
N15 C16 S2 178.5(5) . . ?
N17 C18 S3 178.6(5) . . ?
N19 C20 S4 178.2(6) . . ?
N17A Co1A N13A 109.9(2) . . ?
N17A Co1A N19A 109.9(2) . . ?
N13A Co1A N19A 105.01(19) . . ?
N17A Co1A N15A 109.1(2) . . ?
N13A Co1A N15A 115.5(2) . . ?
N19A Co1A N15A 107.2(2) . . ?
C14A N13A Co1A 162.5(5) . . ?
C16A N15A Co1A 158.4(5) . . ?
C18A N17A Co1A 177.1(5) . . ?
C20A N19A Co1A 176.0(6) . . ?
N13A C14A S1A 178.9(6) . . ?
N15A C16A S2A 179.5(6) . . ?
N17A C18A S3A 178.2(6) . . ?
N19A C20A S4A 179.6(7) . . ?
C7 N4 C5 120.7(4) . . ?
C7 N4 C3 125.5(5) . . ?
C5 N4 C3 113.6(4) . . ?
C6 N1 C2 112.7(4) . . ?
C6 N1 H1A 112(3) . . ?
C2 N1 H1A 108(4) . . ?
C6 N1 H1B 107(3) . . ?
C2 N1 H1B 105(4) . . ?
H1A N1 H1B 112(5) . . ?
C9 N8 C7 117.3(5) . . ?
C7 N12 C11 121.2(5) . . ?
C7 N12 H12 123(4) . . ?
C11 N12 H12 115(4) . . ?
N1 C2 C3 110.8(4) . . ?
N1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
N4 C3 C2 109.9(4) . . ?
N4 C3 H3A 109.7 . . ?
C2 C3 H3A 109.7 . . ?
N4 C3 H3B 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
N4 C5 C6 110.8(5) . . ?
N4 C5 H5A 109.5 . . ?
C6 C5 H5A 109.5 . . ?
N4 C5 H5B 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
N1 C6 C5 109.7(4) . . ?
N1 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
N1 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N4 C7 N8 118.4(5) . . ?
N4 C7 N12 120.8(5) . . ?
N8 C7 N12 120.8(5) . . ?
N8 C9 C10 124.4(6) . . ?
N8 C9 H9 117.8 . . ?
C10 C9 H9 117.8 . . ?
C11 C10 C9 116.6(6) . . ?
C11 C10 H10 121.7 . . ?
C9 C10 H10 121.7 . . ?
C10 C11 N12 119.6(5) . . ?
C10 C11 H11 120.2 . . ?
N12 C11 H11 120.2 . . ?
C7A N4A C5A 120.8(5) . . ?
C7A N4A C3A 123.9(5) . . ?
C5A N4A C3A 113.0(5) . . ?
C2A N1A C6A 111.2(5) . . ?
C2A N1A H1C 112(4) . . ?
C6A N1A H1C 109(4) . . ?
C2A N1A H1D 113(4) . . ?
C6A N1A H1D 104(4) . . ?
H1C N1A H1D 108(6) . . ?
C9A N8A C7A 117.5(5) . . ?
C11A N12A C7A 120.5(5) . . ?
C11A N12A H12A 113(4) . . ?
C7A N12A H12A 126(4) . . ?
N1A C2A C3A 110.2(6) . . ?
N1A C2A H2C 109.6 . . ?
C3A C2A H2C 109.6 . . ?
N1A C2A H2D 109.6 . . ?
C3A C2A H2D 109.6 . . ?
H2C C2A H2D 108.1 . . ?
N4A C3A C2A 110.1(5) . . ?
N4A C3A H3C 109.7 . . ?
C2A C3A H3C 109.7 . . ?
N4A C3A H3D 109.7 . . ?
C2A C3A H3D 109.7 . . ?
H3C C3A H3D 108.2 . . ?
N4A C5A C6A 111.5(5) . . ?
N4A C5A H5C 109.3 . . ?
C6A C5A H5C 109.3 . . ?
N4A C5A H5D 109.3 . . ?
C6A C5A H5D 109.3 . . ?
H5C C5A H5D 108.0 . . ?
C5A C6A N1A 110.8(5) . . ?
C5A C6A H6C 109.5 . . ?
N1A C6A H6C 109.5 . . ?
C5A C6A H6D 109.5 . . ?
N1A C6A H6D 109.5 . . ?
H6C C6A H6D 108.1 . . ?
N8A C7A N4A 118.5(5) . . ?
N8A C7A N12A 121.3(5) . . ?
N4A C7A N12A 120.2(5) . . ?
N8A C9A C10A 123.8(6) . . ?
N8A C9A H9A 118.1 . . ?
C10A C9A H9A 118.1 . . ?
C11A C10A C9A 116.9(5) . . ?
C11A C10A H10A 121.5 . . ?
C9A C10A H10A 121.5 . . ?
N12A C11A C10A 120.0(5) . . ?
N12A C11A H11A 120.0 . . ?
C10A C11A H11A 120.0 . . ?
H1O O1 H1P 112(7) . . ?
H2O O2 H2P 110(8) . . ?

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
C6 N1 C2 C3 54.8(6) . . . . ?
C7 N4 C3 C2 -129.4(5) . . . . ?
C5 N4 C3 C2 56.2(6) . . . . ?
N1 C2 C3 N4 -53.6(6) . . . . ?
C7 N4 C5 C6 127.9(5) . . . . ?
C3 N4 C5 C6 -57.4(6) . . . . ?
C2 N1 C6 C5 -54.9(6) . . . . ?
N4 C5 C6 N1 54.8(6) . . . . ?
C5 N4 C7 N8 -13.0(7) . . . . ?
C3 N4 C7 N8 172.9(5) . . . . ?
C5 N4 C7 N12 165.8(5) . . . . ?
C3 N4 C7 N12 -8.3(8) . . . . ?
C9 N8 C7 N4 -178.5(5) . . . . ?
C9 N8 C7 N12 2.7(7) . . . . ?
C11 N12 C7 N4 178.1(5) . . . . ?
C11 N12 C7 N8 -3.1(8) . . . . ?
C7 N8 C9 C10 -0.4(8) . . . . ?
N8 C9 C10 C11 -1.6(9) . . . . ?
C9 C10 C11 N12 1.2(8) . . . . ?
C7 N12 C11 C10 1.0(8) . . . . ?
C6A N1A C2A C3A 57.0(7) . . . . ?
C7A N4A C3A C2A -140.2(6) . . . . ?
C5A N4A C3A C2A 56.7(7) . . . . ?
N1A C2A C3A N4A -57.2(7) . . . . ?
C7A N4A C5A C6A 141.1(6) . . . . ?
C3A N4A C5A C6A -55.2(7) . . . . ?
N4A C5A C6A N1A 53.0(7) . . . . ?
C2A N1A C6A C5A -55.0(7) . . . . ?
C9A N8A C7A N4A 179.1(5) . . . . ?
C9A N8A C7A N12A -1.6(8) . . . . ?
C5A N4A C7A N8A -10.5(8) . . . . ?
C3A N4A C7A N8A -172.3(6) . . . . ?
C5A N4A C7A N12A 170.2(6) . . . . ?
C3A N4A C7A N12A 8.3(9) . . . . ?
C11A N12A C7A N8A 1.0(8) . . . . ?
C11A N12A C7A N4A -179.6(5) . . . . ?
C7A N8A C9A C10A 0.3(9) . . . . ?
N8A C9A C10A C11A 1.5(9) . . . . ?
C7A N12A C11A C10A 0.9(9) . . . . ?
C9A C10A C11A N12A -2.1(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A S2A 0.89(2) 2.45(3) 3.326(5) 167(5) .
N1 H1B S4A 0.91(2) 2.47(3) 3.292(5) 151(5) 3
N12 H12 S3A 0.89(2) 2.35(3) 3.198(5) 160(5) .
N1A H1C S1A 0.91(3) 2.55(4) 3.354(6) 148(5) 3
N1A H1D O1 0.90(3) 1.84(4) 2.694(7) 158(6) .
N12A H12A O2 0.87(3) 1.84(3) 2.685(7) 162(5) .
O1 H1O S3 0.84(3) 2.53(3) 3.342(5) 164(6) 4_645
O1 H1P S2 0.83(3) 2.47(4) 3.244(5) 156(6) 2_665
O2 H2O S3 0.85(2) 2.48(2) 3.281(5) 157(6) 2_765
O2 H2P S4 0.85(2) 2.48(2) 3.332(6) 173(8) 4_645

_refine_diff_density_max         0.474
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.080
