# 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_JTM772_5
_database_code_depnum_ccdc_archive 'CCDC 1920804'
loop_
_audit_author_name
_audit_author_address
'Joel T. Mague'
;Tulane University
United States of America
;
_audit_update_record             
;
2020-04-21 deposited with the CCDC.	2020-04-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 N6 O2 S4 Zn'
_chemical_formula_sum            'C22 H20 N6 O2 S4 Zn'
_chemical_formula_weight         594.05

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 '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                   17.0306(6)
_cell_length_b                   15.5145(6)
_cell_length_c                   10.2986(4)
_cell_angle_alpha                90
_cell_angle_beta                 113.411(2)
_cell_angle_gamma                90
_cell_volume                     2497.10(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9617
_cell_measurement_theta_min      4.0150
_cell_measurement_theta_max      72.3601
_cell_measurement_temperature    150(2)

_exptl_crystal_description       column
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   0.506
_exptl_transmission_factor_max   0.806
_exptl_crystal_size_max          0.106
_exptl_crystal_size_mid          0.037
_exptl_crystal_size_min          0.028
_exptl_absorpt_coefficient_mu    4.775
_shelx_estimated_absorpt_T_min   0.632
_shelx_estimated_absorpt_T_max   0.878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS (Sheldrick, 2009)'
_exptl_absorpt_correction_T_min  0.63
_exptl_absorpt_correction_T_max  0.88

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'INCOATEC I\mS micro--focus source'
_diffrn_radiation_monochromator  mirror

_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            17812
_diffrn_reflns_av_unetI/netI     0.0934
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.015
_diffrn_reflns_theta_max         72.413
_diffrn_reflns_theta_full        69.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             17812
_reflns_number_gt                12355
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT  (Bruker, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  
'SHELXL 2014/7 (Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2012)'
_computing_publication_material  'SHELXTL (Bruker, 2016)'

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. H-atoms attached to carbon
were placed in calculated positions (C---H = 0.95 - 0.99 Å) while those
attached to nitrogen were placed in locations derived from a difference
map and their parameters adjusted to give N---H = 0.91 Å. All were 
included as riding contributions with isotropic displacement parameters 
1.2 - 1.5 times those of the attached atoms. Refined as a 2-component 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)+(0.0803P)²+4.8474P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         17812
_refine_ls_number_parameters     161
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.0757
_refine_ls_wR_factor_ref         0.2018
_refine_ls_wR_factor_gt          0.1783
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
Zn1 Zn 0.500000 0.28108(7) 0.250000 0.0347(4) Uani 1 2 d S T P . .
S1 S 0.54247(10) 0.19810(10) 0.09815(17) 0.0353(4) Uani 1 1 d . . . . .
S2 S 0.71607(10) 0.17126(10) 0.12609(17) 0.0355(4) Uani 1 1 d . . . . .
O1 O 0.5064(3) 0.4110(3) 0.4024(5) 0.0384(11) Uani 1 1 d . . . . .
N1 N 0.6226(3) 0.4934(3) 0.5432(6) 0.0324(11) Uani 1 1 d . . . . .
H1 H 0.590710 0.527381 0.575630 0.039 Uiso 1 1 d R U . . .
N2 N 0.6259(3) 0.3206(3) 0.3325(5) 0.0275(10) Uani 1 1 d . . . . .
N3 N 0.6840(3) 0.2807(3) 0.2917(5) 0.0270(10) Uani 1 1 d . . . . .
C1 C 0.5830(4) 0.4291(4) 0.4539(7) 0.0313(13) Uani 1 1 d . . . . .
C2 C 0.7116(4) 0.4929(4) 0.5764(7) 0.0304(13) Uani 1 1 d . . . . .
C3 C 0.7728(4) 0.5462(4) 0.6668(7) 0.0351(13) Uani 1 1 d . . . . .
H3 H 0.758282 0.591308 0.715628 0.042 Uiso 1 1 calc R U . . .
C4 C 0.8569(4) 0.5319(4) 0.6845(7) 0.0383(14) Uani 1 1 d . . . . .
H4 H 0.900774 0.568241 0.746348 0.046 Uiso 1 1 calc R U . . .
C5 C 0.8784(4) 0.4653(4) 0.6134(7) 0.0367(14) Uani 1 1 d . . . . .
H5 H 0.936466 0.457083 0.627247 0.044 Uiso 1 1 calc R U . . .
C6 C 0.8160(4) 0.4113(4) 0.5230(6) 0.0317(13) Uani 1 1 d . . . . .
H6 H 0.830700 0.365615 0.475417 0.038 Uiso 1 1 calc R U . . .
C7 C 0.7315(4) 0.4250(4) 0.5030(6) 0.0290(12) Uani 1 1 d . . . . .
C8 C 0.6511(4) 0.3830(4) 0.4219(6) 0.0297(12) Uani 1 1 d . . . . .
C9 C 0.6484(4) 0.2252(4) 0.1870(6) 0.0281(12) Uani 1 1 d . . . . .
C10 C 0.8205(4) 0.2113(4) 0.2380(8) 0.0384(14) Uani 1 1 d . . . . .
H10A H 0.825081 0.273254 0.218987 0.046 Uiso 1 1 calc R U . . .
H10B H 0.830061 0.204617 0.338755 0.046 Uiso 1 1 calc R U . . .
C11 C 0.8869(5) 0.1599(6) 0.2063(9) 0.059(2) Uani 1 1 d . . . . .
H11A H 0.878983 0.169496 0.107822 0.088 Uiso 1 1 calc R U . . .
H11B H 0.880154 0.098399 0.221161 0.088 Uiso 1 1 calc R U . . .
H11C H 0.944410 0.178608 0.269556 0.088 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
Zn1 N2 2.061(5) . ?
Zn1 N2 2.061(5) 2_655 ?
Zn1 S1 2.3505(16) . ?
Zn1 S1 2.3505(16) 2_655 ?
S1 C9 1.719(6) . ?
S2 C9 1.731(6) . ?
S2 C10 1.803(7) . ?
O1 C1 1.229(7) . ?
N1 C1 1.343(8) . ?
N1 C2 1.416(8) . ?
N1 H1 0.9099 . ?
N2 C8 1.286(8) . ?
N2 N3 1.366(6) . ?
N3 C9 1.325(8) . ?
C1 C8 1.507(8) . ?
C2 C3 1.365(9) . ?
C2 C7 1.414(8) . ?
C3 C4 1.388(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.397(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.387(8) . ?
C6 H6 0.9500 . ?
C7 C8 1.445(9) . ?
C10 C11 1.522(9) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

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
S1 Zn1 O1 154.19(13) . . ?
S1 Zn1 O1 154.19(13) 2_655 2_655 ?
S1 Zn1 O1 88.42(12) . 2_655 ?
O1 Zn1 S1 88.42(12) . 2_655 ?
O1 Zn1 O1 74.38(16) . 2_655 ?
O1 Zn1 N2 74.09(18) . . ?
O1 Zn1 N2 74.09(18) 2_655 2_655 ?
O1 Zn1 N2 78.47(18) . 2_655 ?
N2 Zn1 O1 78.47(18) . 2_655 ?
N2 Zn1 N2 145.4(3) 2_655 . ?
N2 Zn1 S1 115.69(14) 2_655 . ?
N2 Zn1 S1 83.82(13) . . ?
N2 Zn1 S1 83.82(13) 2_655 2_655 ?
N2 Zn1 S1 115.69(14) . 2_655 ?
S1 Zn1 S1 113.58(9) . 2_655 ?
C9 S1 Zn1 92.71(19) . . ?
C9 S2 C10 103.4(3) . . ?
C1 N1 C2 111.1(5) . . ?
C1 N1 H1 118.1 . . ?
C2 N1 H1 130.7 . . ?
C8 N2 N3 118.9(5) . . ?
C8 N2 Zn1 121.0(4) . . ?
N3 N2 Zn1 120.0(4) . . ?
C9 N3 N2 113.0(5) . . ?
O1 C1 N1 128.5(5) . . ?
O1 C1 C8 125.1(5) . . ?
N1 C1 C8 106.4(5) . . ?
C3 C2 C7 122.4(6) . . ?
C3 C2 N1 128.0(5) . . ?
C7 C2 N1 109.6(5) . . ?
C2 C3 C4 117.5(6) . . ?
C2 C3 H3 121.3 . . ?
C4 C3 H3 121.3 . . ?
C3 C4 C5 121.4(6) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 120.7(6) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 118.8(6) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C6 C7 C2 119.3(6) . . ?
C6 C7 C8 134.8(5) . . ?
C2 C7 C8 105.8(5) . . ?
N2 C8 C7 136.3(5) . . ?
N2 C8 C1 116.5(5) . . ?
C7 C8 C1 107.1(5) . . ?
N3 C9 S1 129.6(4) . . ?
N3 C9 S2 117.0(4) . . ?
S1 C9 S2 113.5(3) . . ?
C11 C10 S2 108.1(6) . . ?
C11 C10 H10A 110.1 . . ?
S2 C10 H10A 110.1 . . ?
C11 C10 H10B 110.1 . . ?
S2 C10 H10B 110.1 . . ?
H10A C10 H10B 108.4 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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
C8 N2 N3 C9 -172.1(5) . . . . ?
Zn1 N2 N3 C9 7.5(6) . . . . ?
C2 N1 C1 O1 -179.3(6) . . . . ?
C2 N1 C1 C8 -1.4(7) . . . . ?
C1 N1 C2 C3 -177.6(6) . . . . ?
C1 N1 C2 C7 0.8(7) . . . . ?
C7 C2 C3 C4 0.4(9) . . . . ?
N1 C2 C3 C4 178.6(6) . . . . ?
C2 C3 C4 C5 -0.4(10) . . . . ?
C3 C4 C5 C6 -0.2(10) . . . . ?
C4 C5 C6 C7 0.7(9) . . . . ?
C5 C6 C7 C2 -0.7(9) . . . . ?
C5 C6 C7 C8 -178.8(6) . . . . ?
C3 C2 C7 C6 0.1(9) . . . . ?
N1 C2 C7 C6 -178.4(5) . . . . ?
C3 C2 C7 C8 178.7(6) . . . . ?
N1 C2 C7 C8 0.2(6) . . . . ?
N3 N2 C8 C7 -3.0(10) . . . . ?
Zn1 N2 C8 C7 177.4(6) . . . . ?
N3 N2 C8 C1 175.2(5) . . . . ?
Zn1 N2 C8 C1 -4.4(7) . . . . ?
C6 C7 C8 N2 -4.4(13) . . . . ?
C2 C7 C8 N2 177.3(7) . . . . ?
C6 C7 C8 C1 177.2(6) . . . . ?
C2 C7 C8 C1 -1.0(6) . . . . ?
O1 C1 C8 N2 0.8(9) . . . . ?
N1 C1 C8 N2 -177.2(5) . . . . ?
O1 C1 C8 C7 179.5(6) . . . . ?
N1 C1 C8 C7 1.5(7) . . . . ?
N2 N3 C9 S1 0.4(8) . . . . ?
N2 N3 C9 S2 179.7(4) . . . . ?
Zn1 S1 C9 N3 -6.2(5) . . . . ?
Zn1 S1 C9 S2 174.5(3) . . . . ?
C10 S2 C9 N3 1.2(5) . . . . ?
C10 S2 C9 S1 -179.5(3) . . . . ?
C9 S2 C10 C11 173.0(5) . . . . ?

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
_geom_hbond_publ_flag
N1 H1 O1 0.91 2.00 2.883(6) 163.6 5_666 yes
C3 H3 N3 0.95 2.64 3.563(8) 165.7 6_566 yes

_refine_diff_density_max         0.906
_refine_diff_density_min         -0.706
_refine_diff_density_rms         0.139

####################################################################### 
# 
# 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_JTM771_0m
_audit_block_doi                 10.5517/ccdc.csd.cc22grkw
_database_code_depnum_ccdc_archive 'CCDC 1920808'
loop_
_audit_author_name
_audit_author_address
'Joel T. Mague'
;Tulane University
United States of America
;
_audit_update_record             
;
2019-06-04 deposited with the CCDC.	2020-04-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 N6 O2 Pd S4'
_chemical_formula_sum            'C22 H20 N6 O2 Pd S4'
_chemical_formula_weight         635.08

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'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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'

_cell_length_a                   8.555(2)
_cell_length_b                   21.607(6)
_cell_length_c                   13.272(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.413(4)
_cell_angle_gamma                90
_cell_volume                     2427.1(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5120
_cell_measurement_theta_min      2.4414
_cell_measurement_theta_max      27.8976
_cell_measurement_temperature    100(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.738
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   0.352
_exptl_transmission_factor_max   0.694
_exptl_crystal_size_max          0.199
_exptl_crystal_size_mid          0.093
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    1.143
_shelx_estimated_absorpt_T_min   0.804
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_correction_T_min  0.49
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
The diffraction data were collected in three sets of 
363 frames (0.5° width in ω) at φ = 0, 120 
and 240°. A scan time of 80 sec/frame was used. 
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker Smart APEX CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            22752
_diffrn_reflns_av_unetI/netI     0.1027
_diffrn_reflns_av_R_equivalents  0.0919
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.815
_diffrn_reflns_theta_max         28.750
_diffrn_reflns_theta_full        28.250
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             6141
_reflns_number_gt                4372
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2012)'
_computing_publication_material  'SHELXTL (Bruker, 2016)'

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. H-atoms attached to carbon 
were placed in calculated positions (C---H = 0.95 - 0.99 Å) while those 
attached to nitrogen were placed in locations derived from a difference 
map and their coordinates adjusted to give N---H = 0.91 %A. All were included 
as riding contributions with isotropic displacement parameters 1.2 - 1.5 
times those of the attached atoms.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0967P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6141
_refine_ls_number_parameters     318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0630
_refine_ls_wR_factor_ref         0.1693
_refine_ls_wR_factor_gt          0.1537
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_restrained_S_all      0.982
_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
Pd1 Pd 0.25003(4) 0.70320(2) 0.55898(3) 0.01822(13) Uani 1 1 d . . . . .
S1 S 0.33493(15) 0.76656(5) 0.68854(9) 0.0222(3) Uani 1 1 d . . . . .
S2 S 0.54431(16) 0.74432(6) 0.87539(10) 0.0269(3) Uani 1 1 d . . . . .
S3 S 0.16397(15) 0.78809(5) 0.47013(10) 0.0229(3) Uani 1 1 d . . . . .
S4 S -0.05041(16) 0.79961(5) 0.28382(10) 0.0269(3) Uani 1 1 d . . . . .
O1 O 0.0442(4) 0.57941(14) 0.5398(3) 0.0247(7) Uani 1 1 d . . . . .
O2 O 0.4534(4) 0.58496(14) 0.5113(3) 0.0241(7) Uani 1 1 d . . . . .
N1 N 0.1577(5) 0.48835(17) 0.6067(3) 0.0252(9) Uani 1 1 d . . . . .
H1 H 0.0882 0.4657 0.5630 0.030 Uiso 1 1 d R U . . .
N2 N 0.3080(4) 0.63503(17) 0.6757(3) 0.0198(8) Uani 1 1 d . . . . .
N3 N 0.4157(5) 0.65198(18) 0.7597(3) 0.0230(9) Uani 1 1 d . . . . .
N4 N 0.3420(4) 0.51209(17) 0.3958(3) 0.0222(9) Uani 1 1 d . . . . .
H4A H 0.4075 0.4802 0.4183 0.027 Uiso 1 1 d R U . . .
N5 N 0.1875(4) 0.66054(17) 0.4136(3) 0.0193(8) Uani 1 1 d . . . . .
N6 N 0.0732(5) 0.69128(17) 0.3452(3) 0.0203(8) Uani 1 1 d . . . . .
C1 C 0.1429(6) 0.5511(2) 0.5978(4) 0.0220(10) Uani 1 1 d . . . . .
C2 C 0.2723(5) 0.4720(2) 0.6877(4) 0.0231(10) Uani 1 1 d . . . . .
C3 C 0.3222(6) 0.4134(2) 0.7166(4) 0.0299(12) Uani 1 1 d . . . . .
H3 H 0.2798 0.3778 0.6803 0.036 Uiso 1 1 calc R U . . .
C4 C 0.4382(7) 0.4085(2) 0.8018(4) 0.0362(13) Uani 1 1 d . . . . .
H4 H 0.4749 0.3687 0.8245 0.043 Uiso 1 1 calc R U . . .
C5 C 0.5011(6) 0.4604(2) 0.8543(4) 0.0344(13) Uani 1 1 d . . . . .
H5 H 0.5788 0.4555 0.9127 0.041 Uiso 1 1 calc R U . . .
C6 C 0.4516(6) 0.5197(2) 0.8223(4) 0.0278(11) Uani 1 1 d . . . . .
H6 H 0.4955 0.5553 0.8577 0.033 Uiso 1 1 calc R U . . .
C7 C 0.3376(6) 0.5253(2) 0.7380(4) 0.0235(10) Uani 1 1 d . . . . .
C8 C 0.2676(5) 0.5776(2) 0.6768(3) 0.0192(9) Uani 1 1 d . . . . .
C9 C 0.5667(6) 0.6811(2) 0.9670(4) 0.0269(11) Uani 1 1 d . . . . .
H9A H 0.5685 0.6985 1.0361 0.032 Uiso 1 1 calc R U . . .
H9B H 0.4731 0.6538 0.9531 0.032 Uiso 1 1 calc R U . . .
C10 C 0.4292(6) 0.7115(2) 0.7696(4) 0.0210(10) Uani 1 1 d . . . . .
C11 C 0.7126(6) 0.6426(2) 0.9660(4) 0.0309(11) Uani 1 1 d . . . . .
H11A H 0.7173 0.6105 1.0186 0.046 Uiso 1 1 calc R U . . .
H11B H 0.8063 0.6691 0.9797 0.046 Uiso 1 1 calc R U . . .
H11C H 0.7094 0.6231 0.8991 0.046 Uiso 1 1 calc R U . . .
C12 C 0.3568(5) 0.5691(2) 0.4397(4) 0.0207(9) Uani 1 1 d . . . . .
C13 C 0.2269(5) 0.5117(2) 0.3088(4) 0.0201(9) Uani 1 1 d . . . . .
C14 C 0.1782(5) 0.4621(2) 0.2474(4) 0.0229(10) Uani 1 1 d . . . . .
H14 H 0.2218 0.4221 0.2613 0.027 Uiso 1 1 calc R U . . .
C15 C 0.0639(6) 0.4728(2) 0.1651(4) 0.0259(11) Uani 1 1 d . . . . .
H15 H 0.0279 0.4393 0.1214 0.031 Uiso 1 1 calc R U . . .
C16 C -0.0009(6) 0.5316(2) 0.1440(4) 0.0275(11) Uani 1 1 d . . . . .
H16 H -0.0782 0.5377 0.0857 0.033 Uiso 1 1 calc R U . . .
C17 C 0.0468(6) 0.5813(2) 0.2075(4) 0.0236(10) Uani 1 1 d . . . . .
H17 H 0.0030 0.6213 0.1936 0.028 Uiso 1 1 calc R U . . .
C18 C 0.1607(5) 0.5709(2) 0.2923(3) 0.0185(9) Uani 1 1 d . . . . .
C19 C 0.2285(5) 0.6079(2) 0.3789(3) 0.0193(9) Uani 1 1 d . . . . .
C20 C 0.0639(6) 0.7497(2) 0.3659(4) 0.0223(10) Uani 1 1 d . . . . .
C21 C -0.1196(6) 0.7540(2) 0.1718(4) 0.0256(11) Uani 1 1 d . . . . .
H21A H -0.0306 0.7314 0.1487 0.031 Uiso 1 1 calc R U . . .
H21B H -0.1994 0.7235 0.1869 0.031 Uiso 1 1 calc R U . . .
C22 C -0.1915(7) 0.7986(2) 0.0912(5) 0.0386(14) Uani 1 1 d . . . . .
H22A H -0.2147 0.7769 0.0258 0.058 Uiso 1 1 calc R U . . .
H22B H -0.1171 0.8324 0.0851 0.058 Uiso 1 1 calc R U . . .
H22C H -0.2895 0.8155 0.1100 0.058 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
Pd1 N5 2.135(4) . ?
Pd1 N2 2.143(4) . ?
Pd1 S1 2.2347(13) . ?
Pd1 S3 2.2458(13) . ?
S1 C10 1.724(5) . ?
S2 C10 1.743(5) . ?
S2 C9 1.820(5) . ?
S3 C20 1.728(5) . ?
S4 C20 1.731(5) . ?
S4 C21 1.809(5) . ?
O1 C1 1.221(6) . ?
O2 C12 1.214(6) . ?
N1 C1 1.365(6) . ?
N1 C2 1.391(6) . ?
N1 H1 0.9100 . ?
N2 C8 1.288(5) . ?
N2 N3 1.387(5) . ?
N3 C10 1.296(6) . ?
N4 C12 1.361(6) . ?
N4 C13 1.404(6) . ?
N4 H4A 0.9101 . ?
N5 C19 1.295(6) . ?
N5 N6 1.400(5) . ?
N6 C20 1.297(6) . ?
C1 C8 1.496(6) . ?
C2 C3 1.374(6) . ?
C2 C7 1.404(6) . ?
C3 C4 1.395(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.396(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.378(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.468(6) . ?
C9 C11 1.501(7) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C19 1.516(6) . ?
C13 C14 1.374(6) . ?
C13 C18 1.402(6) . ?
C14 C15 1.375(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.398(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(7) . ?
C16 H16 0.9500 . ?
C17 C18 1.394(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.450(6) . ?
C21 C22 1.503(7) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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
N5 Pd1 N2 110.97(14) . . ?
N5 Pd1 S1 166.01(10) . . ?
N2 Pd1 S1 81.37(11) . . ?
N5 Pd1 S3 81.86(11) . . ?
N2 Pd1 S3 164.70(11) . . ?
S1 Pd1 S3 87.03(5) . . ?
C10 S1 Pd1 97.30(16) . . ?
C10 S2 C9 103.0(2) . . ?
C20 S3 Pd1 96.55(16) . . ?
C20 S4 C21 105.4(2) . . ?
C1 N1 C2 111.3(4) . . ?
C1 N1 H1 115.8 . . ?
C2 N1 H1 132.7 . . ?
C8 N2 N3 113.2(4) . . ?
C8 N2 Pd1 129.5(3) . . ?
N3 N2 Pd1 117.1(3) . . ?
C10 N3 N2 112.5(4) . . ?
C12 N4 C13 111.5(4) . . ?
C12 N4 H4A 122.0 . . ?
C13 N4 H4A 126.2 . . ?
C19 N5 N6 112.7(4) . . ?
C19 N5 Pd1 131.0(3) . . ?
N6 N5 Pd1 116.1(3) . . ?
C20 N6 N5 112.5(4) . . ?
O1 C1 N1 126.7(4) . . ?
O1 C1 C8 127.4(4) . . ?
N1 C1 C8 105.8(4) . . ?
C3 C2 N1 127.2(5) . . ?
C3 C2 C7 122.6(5) . . ?
N1 C2 C7 110.2(4) . . ?
C2 C3 C4 116.8(5) . . ?
C2 C3 H3 121.6 . . ?
C4 C3 H3 121.6 . . ?
C5 C4 C3 121.6(5) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 120.7(5) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 118.4(5) . . ?
C7 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
C6 C7 C2 119.9(4) . . ?
C6 C7 C8 134.4(4) . . ?
C2 C7 C8 105.5(4) . . ?
N2 C8 C7 131.2(4) . . ?
N2 C8 C1 121.7(4) . . ?
C7 C8 C1 106.5(4) . . ?
C11 C9 S2 114.6(4) . . ?
C11 C9 H9A 108.6 . . ?
S2 C9 H9A 108.6 . . ?
C11 C9 H9B 108.6 . . ?
S2 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
N3 C10 S1 126.5(4) . . ?
N3 C10 S2 121.1(4) . . ?
S1 C10 S2 112.3(3) . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 N4 126.9(4) . . ?
O2 C12 C19 128.2(4) . . ?
N4 C12 C19 104.9(4) . . ?
C14 C13 C18 122.5(4) . . ?
C14 C13 N4 127.4(4) . . ?
C18 C13 N4 110.0(4) . . ?
C13 C14 C15 117.3(4) . . ?
C13 C14 H14 121.3 . . ?
C15 C14 H14 121.3 . . ?
C14 C15 C16 121.8(4) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C17 C16 C15 120.5(5) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 118.3(4) . . ?
C16 C17 H17 120.8 . . ?
C18 C17 H17 120.8 . . ?
C17 C18 C13 119.5(4) . . ?
C17 C18 C19 134.6(4) . . ?
C13 C18 C19 105.8(4) . . ?
N5 C19 C18 132.0(4) . . ?
N5 C19 C12 120.6(4) . . ?
C18 C19 C12 107.0(4) . . ?
N6 C20 S3 126.7(4) . . ?
N6 C20 S4 121.3(4) . . ?
S3 C20 S4 111.9(3) . . ?
C22 C21 S4 106.7(3) . . ?
C22 C21 H21A 110.4 . . ?
S4 C21 H21A 110.4 . . ?
C22 C21 H21B 110.4 . . ?
S4 C21 H21B 110.4 . . ?
H21A C21 H21B 108.6 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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
C8 N2 N3 C10 -165.9(4) . . . . ?
Pd1 N2 N3 C10 19.6(5) . . . . ?
C19 N5 N6 C20 -162.1(4) . . . . ?
Pd1 N5 N6 C20 22.8(5) . . . . ?
C2 N1 C1 O1 -173.6(5) . . . . ?
C2 N1 C1 C8 3.9(5) . . . . ?
C1 N1 C2 C3 -177.5(5) . . . . ?
C1 N1 C2 C7 1.0(5) . . . . ?
N1 C2 C3 C4 -179.2(5) . . . . ?
C7 C2 C3 C4 2.5(7) . . . . ?
C2 C3 C4 C5 -0.6(8) . . . . ?
C3 C4 C5 C6 -0.9(8) . . . . ?
C4 C5 C6 C7 0.7(8) . . . . ?
C5 C6 C7 C2 1.1(7) . . . . ?
C5 C6 C7 C8 -173.2(5) . . . . ?
C3 C2 C7 C6 -2.8(7) . . . . ?
N1 C2 C7 C6 178.6(4) . . . . ?
C3 C2 C7 C8 173.0(5) . . . . ?
N1 C2 C7 C8 -5.5(5) . . . . ?
N3 N2 C8 C7 -14.4(7) . . . . ?
Pd1 N2 C8 C7 159.3(4) . . . . ?
N3 N2 C8 C1 175.0(4) . . . . ?
Pd1 N2 C8 C1 -11.3(6) . . . . ?
C6 C7 C8 N2 10.9(9) . . . . ?
C2 C7 C8 N2 -164.0(5) . . . . ?
C6 C7 C8 C1 -177.4(5) . . . . ?
C2 C7 C8 C1 7.7(5) . . . . ?
O1 C1 C8 N2 -17.0(7) . . . . ?
N1 C1 C8 N2 165.5(4) . . . . ?
O1 C1 C8 C7 170.3(5) . . . . ?
N1 C1 C8 C7 -7.2(5) . . . . ?
C10 S2 C9 C11 93.0(4) . . . . ?
N2 N3 C10 S1 -2.6(6) . . . . ?
N2 N3 C10 S2 174.3(3) . . . . ?
Pd1 S1 C10 N3 -13.3(5) . . . . ?
Pd1 S1 C10 S2 169.6(2) . . . . ?
C9 S2 C10 N3 -17.9(5) . . . . ?
C9 S2 C10 S1 159.4(3) . . . . ?
C13 N4 C12 O2 -174.5(4) . . . . ?
C13 N4 C12 C19 4.8(5) . . . . ?
C12 N4 C13 C14 -178.2(4) . . . . ?
C12 N4 C13 C18 0.2(5) . . . . ?
C18 C13 C14 C15 2.4(7) . . . . ?
N4 C13 C14 C15 -179.4(4) . . . . ?
C13 C14 C15 C16 0.1(7) . . . . ?
C14 C15 C16 C17 -1.3(8) . . . . ?
C15 C16 C17 C18 0.1(7) . . . . ?
C16 C17 C18 C13 2.2(7) . . . . ?
C16 C17 C18 C19 -173.3(5) . . . . ?
C14 C13 C18 C17 -3.5(7) . . . . ?
N4 C13 C18 C17 178.0(4) . . . . ?
C14 C13 C18 C19 173.1(4) . . . . ?
N4 C13 C18 C19 -5.4(5) . . . . ?
N6 N5 C19 C18 -12.0(7) . . . . ?
Pd1 N5 C19 C18 162.2(4) . . . . ?
N6 N5 C19 C12 177.0(4) . . . . ?
Pd1 N5 C19 C12 -8.8(6) . . . . ?
C17 C18 C19 N5 12.0(9) . . . . ?
C13 C18 C19 N5 -163.9(5) . . . . ?
C17 C18 C19 C12 -176.0(5) . . . . ?
C13 C18 C19 C12 8.1(5) . . . . ?
O2 C12 C19 N5 -15.6(7) . . . . ?
N4 C12 C19 N5 165.1(4) . . . . ?
O2 C12 C19 C18 171.3(5) . . . . ?
N4 C12 C19 C18 -8.0(5) . . . . ?
N5 N6 C20 S3 -5.3(6) . . . . ?
N5 N6 C20 S4 171.8(3) . . . . ?
Pd1 S3 C20 N6 -12.3(4) . . . . ?
Pd1 S3 C20 S4 170.3(2) . . . . ?
C21 S4 C20 N6 -6.3(5) . . . . ?
C21 S4 C20 S3 171.2(2) . . . . ?
C20 S4 C21 C22 -168.9(4) . . . . ?

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 O1 0.91 1.91 2.814(5) 174 3_566
N4 H4A O2 0.91 1.99 2.889(5) 171 3_666
C22 H22A S2 0.98 2.74 3.576(6) 143 1_454
C22 H22B O1 0.98 2.48 3.447(7) 170 4_575

_refine_diff_density_max         3.075
_refine_diff_density_min         -1.803
_refine_diff_density_rms         0.202

####################################################################### 
# 
# 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_JTM776_0m
_audit_block_doi                 10.5517/ccdc.csd.cc22grht
_database_code_depnum_ccdc_archive 'CCDC 1920806'
loop_
_audit_author_name
_audit_author_address
'Joel T. Mague'
;Tulane University
United States of America
;
_audit_update_record             
;
2019-06-04 deposited with the CCDC.	2020-04-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 N6 Ni O2 S4'
_chemical_formula_sum            'C22 H20 N6 Ni O2 S4'
_chemical_formula_weight         587.39

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'
Ni Ni 0.3393 1.1124 '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                   16.812(2)
_cell_length_b                   15.539(2)
_cell_length_c                   10.2873(14)
_cell_angle_alpha                90
_cell_angle_beta                 112.258(2)
_cell_angle_gamma                90
_cell_volume                     2487.2(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3665
_cell_measurement_theta_min      2.4262
_cell_measurement_theta_max      28.4591
_cell_measurement_temperature    100(2)

_exptl_crystal_description       column
_exptl_crystal_colour            'dark orange'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_F_000             1208
_exptl_transmission_factor_min   0.688
_exptl_transmission_factor_max   0.914
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    1.149
_shelx_estimated_absorpt_T_min   0.829
_shelx_estimated_absorpt_T_max   0.904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_T_max  0.90

_exptl_special_details           
;
The diffraction data were collected in three sets of 
363 frames (0.5° width in ω) at φ = 0, 120 
and 240°. A scan time of 120 sec/frame was used. 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker Smart APEX CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            11535
_diffrn_reflns_av_unetI/netI     0.0571
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.852
_diffrn_reflns_theta_max         28.676
_diffrn_reflns_theta_full        28.000
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3136
_reflns_number_gt                2294
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2012)'
_computing_publication_material  'SHELXTL (Bruker, 2016)'

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. H-atoms attached to carbon 
were placed in calculated positions (C---H = 0.95 - 0.99 Å) while those 
attached to nitrogen were placed in locations derived from a difference 
map and their coordinates adjusted to give N---H = 0.91 %A. All were included 
as riding contributions with isotropic displacement parameters 1.2 - 1.5 
times those of the attached atoms.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0638P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3136
_refine_ls_number_parameters     160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1093
_refine_ls_wR_factor_gt          0.1003
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_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
Ni1 Ni 0.5000 0.30817(3) 0.2500 0.01899(14) Uani 1 2 d S T P . .
S1 S 0.53513(4) 0.21118(4) 0.10360(7) 0.02261(17) Uani 1 1 d . . . . .
S2 S 0.70750(4) 0.17006(4) 0.11817(7) 0.02425(18) Uani 1 1 d . . . . .
O1 O 0.50799(11) 0.41520(11) 0.39709(19) 0.0237(4) Uani 1 1 d . . . . .
N1 N 0.62442(13) 0.49335(14) 0.5494(2) 0.0209(5) Uani 1 1 d . . . . .
H1 H 0.5938 0.5312 0.5794 0.025 Uiso 1 1 d R U . . .
N2 N 0.62743(13) 0.32432(13) 0.3329(2) 0.0181(4) Uani 1 1 d . . . . .
N3 N 0.68395(13) 0.28192(13) 0.2909(2) 0.0180(4) Uani 1 1 d . . . . .
C1 C 0.58523(16) 0.43156(16) 0.4547(3) 0.0196(5) Uani 1 1 d . . . . .
C2 C 0.71480(15) 0.49179(17) 0.5852(3) 0.0191(5) Uani 1 1 d . . . . .
C3 C 0.77595(17) 0.54451(16) 0.6764(3) 0.0226(5) Uani 1 1 d . . . . .
H3 H 0.7610 0.5897 0.7251 0.027 Uiso 1 1 calc R U . . .
C4 C 0.86112(17) 0.52869(17) 0.6943(3) 0.0255(6) Uani 1 1 d . . . . .
H4 H 0.9051 0.5641 0.7568 0.031 Uiso 1 1 calc R U . . .
C5 C 0.88354(16) 0.46315(17) 0.6239(3) 0.0238(6) Uani 1 1 d . . . . .
H5 H 0.9423 0.4544 0.6386 0.029 Uiso 1 1 calc R U . . .
C6 C 0.82077(15) 0.40960(16) 0.5313(3) 0.0207(5) Uani 1 1 d . . . . .
H6 H 0.8360 0.3642 0.4834 0.025 Uiso 1 1 calc R U . . .
C7 C 0.73563(15) 0.42460(16) 0.5113(3) 0.0189(5) Uani 1 1 d . . . . .
C8 C 0.65471(15) 0.38486(16) 0.4262(3) 0.0184(5) Uani 1 1 d . . . . .
C9 C 0.64296(16) 0.22823(16) 0.1838(3) 0.0200(5) Uani 1 1 d . . . . .
C10 C 0.81515(16) 0.20498(18) 0.2266(3) 0.0264(6) Uani 1 1 d . . . . .
H10A H 0.8222 0.2668 0.2102 0.032 Uiso 1 1 calc R U . . .
H10B H 0.8253 0.1970 0.3271 0.032 Uiso 1 1 calc R U . . .
C11 C 0.87891(18) 0.1520(2) 0.1888(3) 0.0380(8) Uani 1 1 d . . . . .
H11A H 0.9373 0.1648 0.2549 0.057 Uiso 1 1 calc R U . . .
H11B H 0.8739 0.1664 0.0933 0.057 Uiso 1 1 calc R U . . .
H11C H 0.8668 0.0907 0.1939 0.057 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
Ni1 N2 1.999(2) 2_655 ?
Ni1 N2 1.999(2) . ?
Ni1 O1 2.2180(18) . ?
Ni1 O1 2.2180(18) 2_655 ?
Ni1 S1 2.3584(7) 2_655 ?
Ni1 S1 2.3585(7) . ?
S1 C9 1.704(3) . ?
S2 C9 1.734(3) . ?
S2 C10 1.812(3) . ?
O1 C1 1.233(3) . ?
N1 C1 1.349(3) . ?
N1 C2 1.422(3) . ?
N1 H1 0.9099 . ?
N2 C8 1.297(3) . ?
N2 N3 1.354(3) . ?
N3 C9 1.345(3) . ?
C1 C8 1.495(3) . ?
C2 C3 1.370(4) . ?
C2 C7 1.412(4) . ?
C3 C4 1.395(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.397(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.387(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.448(3) . ?
C10 C11 1.514(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

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
N2 Ni1 N2 165.58(12) 2_655 . ?
N2 Ni1 O1 88.58(7) 2_655 . ?
N2 Ni1 O1 80.60(7) . . ?
N2 Ni1 O1 80.60(7) 2_655 2_655 ?
N2 Ni1 O1 88.58(7) . 2_655 ?
O1 Ni1 O1 82.86(10) . 2_655 ?
N2 Ni1 S1 82.28(6) 2_655 2_655 ?
N2 Ni1 S1 107.15(6) . 2_655 ?
O1 Ni1 S1 90.49(5) . 2_655 ?
O1 Ni1 S1 161.75(5) 2_655 2_655 ?
N2 Ni1 S1 107.15(6) 2_655 . ?
N2 Ni1 S1 82.28(6) . . ?
O1 Ni1 S1 161.75(5) . . ?
O1 Ni1 S1 90.49(5) 2_655 . ?
S1 Ni1 S1 100.56(4) 2_655 . ?
C9 S1 Ni1 93.96(9) . . ?
C9 S2 C10 103.34(13) . . ?
C1 O1 Ni1 105.25(15) . . ?
C1 N1 C2 110.9(2) . . ?
C1 N1 H1 121.4 . . ?
C2 N1 H1 127.6 . . ?
C8 N2 N3 119.6(2) . . ?
C8 N2 Ni1 115.35(16) . . ?
N3 N2 Ni1 124.81(16) . . ?
C9 N3 N2 111.1(2) . . ?
O1 C1 N1 129.1(2) . . ?
O1 C1 C8 124.4(2) . . ?
N1 C1 C8 106.4(2) . . ?
C3 C2 C7 122.4(2) . . ?
C3 C2 N1 128.2(2) . . ?
C7 C2 N1 109.4(2) . . ?
C2 C3 C4 116.8(2) . . ?
C2 C3 H3 121.6 . . ?
C4 C3 H3 121.6 . . ?
C5 C4 C3 122.1(2) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 118.2(2) . . ?
C7 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
C6 C7 C2 119.8(2) . . ?
C6 C7 C8 134.3(2) . . ?
C2 C7 C8 105.9(2) . . ?
N2 C8 C7 138.1(2) . . ?
N2 C8 C1 114.4(2) . . ?
C7 C8 C1 107.4(2) . . ?
N3 C9 S1 127.88(19) . . ?
N3 C9 S2 116.13(19) . . ?
S1 C9 S2 115.99(15) . . ?
C11 C10 S2 108.6(2) . . ?
C11 C10 H10A 110.0 . . ?
S2 C10 H10A 110.0 . . ?
C11 C10 H10B 110.0 . . ?
S2 C10 H10B 110.0 . . ?
H10A C10 H10B 108.4 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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
C8 N2 N3 C9 -173.4(2) . . . . ?
Ni1 N2 N3 C9 1.1(3) . . . . ?
Ni1 O1 C1 N1 177.4(2) . . . . ?
Ni1 O1 C1 C8 -0.7(3) . . . . ?
C2 N1 C1 O1 -177.9(3) . . . . ?
C2 N1 C1 C8 0.6(3) . . . . ?
C1 N1 C2 C3 179.5(3) . . . . ?
C1 N1 C2 C7 -0.9(3) . . . . ?
C7 C2 C3 C4 -0.3(4) . . . . ?
N1 C2 C3 C4 179.2(2) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C4 C5 C6 C7 0.6(4) . . . . ?
C5 C6 C7 C2 -0.9(4) . . . . ?
C5 C6 C7 C8 179.5(3) . . . . ?
C3 C2 C7 C6 0.8(4) . . . . ?
N1 C2 C7 C6 -178.9(2) . . . . ?
C3 C2 C7 C8 -179.5(2) . . . . ?
N1 C2 C7 C8 0.8(3) . . . . ?
N3 N2 C8 C7 -2.0(5) . . . . ?
Ni1 N2 C8 C7 -177.0(3) . . . . ?
N3 N2 C8 C1 175.1(2) . . . . ?
Ni1 N2 C8 C1 0.1(3) . . . . ?
C6 C7 C8 N2 -3.6(5) . . . . ?
C2 C7 C8 N2 176.7(3) . . . . ?
C6 C7 C8 C1 179.2(3) . . . . ?
C2 C7 C8 C1 -0.5(3) . . . . ?
O1 C1 C8 N2 0.5(4) . . . . ?
N1 C1 C8 N2 -178.0(2) . . . . ?
O1 C1 C8 C7 178.5(2) . . . . ?
N1 C1 C8 C7 0.0(3) . . . . ?
N2 N3 C9 S1 0.2(3) . . . . ?
N2 N3 C9 S2 179.53(16) . . . . ?
Ni1 S1 C9 N3 -1.0(2) . . . . ?
Ni1 S1 C9 S2 179.66(13) . . . . ?
C10 S2 C9 N3 0.3(2) . . . . ?
C10 S2 C9 S1 179.68(15) . . . . ?
C9 S2 C10 C11 174.6(2) . . . . ?

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 O1 0.91 2.00 2.864(3) 159 5_666
C3 H3 N3 0.95 2.60 3.526(3) 164 6_566

_refine_diff_density_max         0.744
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.111

####################################################################### 
# 
# 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_jtm769
_audit_block_doi                 10.5517/ccdc.csd.cc22grjv
_database_code_depnum_ccdc_archive 'CCDC 1920807'
loop_
_audit_author_name
_audit_author_address
'Joel T. Mague'
;Tulane University
United States of America
;
_audit_update_record             
;
2019-06-04 deposited with the CCDC.	2020-04-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 N6 O2 Pt S4'
_chemical_formula_sum            'C22 H20 N6 O2 Pt S4'
_chemical_formula_weight         723.77

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'
Pt Pt -1.7033 8.3905 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   22.002(5)
_cell_length_b                   10.401(3)
_cell_length_c                   22.111(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5060(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7405
_cell_measurement_theta_min      2.3536
_cell_measurement_theta_max      26.4860
_cell_measurement_temperature    100(2)

_exptl_crystal_description       column
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.900
_exptl_crystal_F_000             2816
_exptl_transmission_factor_min   0.617
_exptl_transmission_factor_max   0.862
_exptl_crystal_size_max          0.149
_exptl_crystal_size_mid          0.022
_exptl_crystal_size_min          0.016
_exptl_absorpt_coefficient_mu    5.909
_shelx_estimated_absorpt_T_min   0.473
_shelx_estimated_absorpt_T_max   0.911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_T_max  0.91

_exptl_special_details           
;
The diffraction data were collected in three sets of 
363 frames (0.5° width in ω) at φ = 0, 120 
and 240°. A scan time of 120 sec/frame was used. 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker Smart APEX CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            45382
_diffrn_reflns_av_unetI/netI     0.0769
_diffrn_reflns_av_R_equivalents  0.0980
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.842
_diffrn_reflns_theta_max         28.363
_diffrn_reflns_theta_full        28.350
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             6285
_reflns_number_gt                4192
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2012)'
_computing_publication_material  'SHELXTL (Bruker, 2016)'

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. H-atoms attached to carbon 
were placed in calculated positions (C---H = 0.95 - 0.99 Å) while those 
attached to nitrogen were placed in locations derived from a difference 
map and their coordinates adjusted to give N---H = 0.91 %A. All were included 
as riding contributions with isotropic displacement parameters 1.2 - 1.5 
times those of the attached atoms.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0295P)²+4.4960P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6285
_refine_ls_number_parameters     318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.0915
_refine_ls_wR_factor_gt          0.0799
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.003
_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
Pt1 Pt 0.56282(2) 0.41864(2) 0.59456(2) 0.01712(7) Uani 1 1 d . . . . .
S1 S 0.49590(6) 0.49105(14) 0.66428(6) 0.0222(3) Uani 1 1 d . . . . .
S2 S 0.52915(7) 0.67521(17) 0.76642(7) 0.0313(4) Uani 1 1 d . . . . .
S3 S 0.49179(7) 0.33562(14) 0.53212(7) 0.0232(3) Uani 1 1 d . . . . .
S4 S 0.52089(7) 0.14454(16) 0.43301(7) 0.0297(4) Uani 1 1 d . . . . .
O1 O 0.67209(18) 0.2200(4) 0.60355(17) 0.0248(10) Uani 1 1 d . . . . .
O2 O 0.67042(18) 0.6192(4) 0.57710(17) 0.0226(9) Uani 1 1 d . . . . .
N1 N 0.7593(2) 0.2773(4) 0.6542(2) 0.0232(11) Uani 1 1 d . . . . .
H1 H 0.7856 0.2270 0.6331 0.028 Uiso 1 1 d R U . . .
N2 N 0.6242(2) 0.4593(4) 0.6625(2) 0.0174(10) Uani 1 1 d . . . . .
N3 N 0.6079(2) 0.5526(4) 0.7044(2) 0.0223(11) Uani 1 1 d . . . . .
N4 N 0.7572(2) 0.5515(4) 0.5282(2) 0.0219(11) Uani 1 1 d . . . . .
H4A H 0.7814 0.6161 0.5419 0.026 Uiso 1 1 d R U . . .
N5 N 0.6192(2) 0.3789(4) 0.5227(2) 0.0213(11) Uani 1 1 d . . . . .
N6 N 0.6022(2) 0.2846(4) 0.4827(2) 0.0250(11) Uani 1 1 d . . . . .
C1 C 0.7004(3) 0.2911(5) 0.6379(2) 0.0202(12) Uani 1 1 d . . . . .
C2 C 0.7734(3) 0.3616(6) 0.7019(2) 0.0206(12) Uani 1 1 d . . . . .
C3 C 0.8283(3) 0.3661(6) 0.7329(3) 0.0234(13) Uani 1 1 d . . . . .
H3 H 0.8615 0.3117 0.7229 0.028 Uiso 1 1 calc R U . . .
C4 C 0.8316(3) 0.4556(6) 0.7798(3) 0.0248(13) Uani 1 1 d . . . . .
H4 H 0.8678 0.4613 0.8030 0.030 Uiso 1 1 calc R U . . .
C5 C 0.7834(3) 0.5362(6) 0.7933(3) 0.0242(13) Uani 1 1 d . . . . .
H5 H 0.7880 0.5974 0.8249 0.029 Uiso 1 1 calc R U . . .
C6 C 0.7285(3) 0.5302(6) 0.7622(2) 0.0216(13) Uani 1 1 d . . . . .
H6 H 0.6954 0.5848 0.7723 0.026 Uiso 1 1 calc R U . . .
C7 C 0.7243(2) 0.4412(5) 0.7157(2) 0.0179(12) Uani 1 1 d . . . . .
C8 C 0.6767(2) 0.4059(5) 0.6728(2) 0.0172(12) Uani 1 1 d . . . . .
C9 C 0.5493(2) 0.5690(5) 0.7084(2) 0.0182(12) Uani 1 1 d . . . . .
C10 C 0.4470(2) 0.6779(6) 0.7658(3) 0.0273(14) Uani 1 1 d . . . . .
H10A H 0.4322 0.5887 0.7608 0.033 Uiso 1 1 calc R U . . .
H10B H 0.4327 0.7090 0.8056 0.033 Uiso 1 1 calc R U . . .
C11 C 0.4185(3) 0.7609(6) 0.7169(3) 0.0371(16) Uani 1 1 d . . . . .
H11A H 0.4299 0.7276 0.6770 0.056 Uiso 1 1 calc R U . . .
H11B H 0.4330 0.8496 0.7210 0.056 Uiso 1 1 calc R U . . .
H11C H 0.3742 0.7592 0.7210 0.056 Uiso 1 1 calc R U . . .
C12 C 0.6977(3) 0.5437(5) 0.5445(3) 0.0201(12) Uani 1 1 d . . . . .
C13 C 0.7722(3) 0.4588(6) 0.4846(3) 0.0220(13) Uani 1 1 d . . . . .
C14 C 0.8274(3) 0.4407(6) 0.4560(3) 0.0291(15) Uani 1 1 d . . . . .
H14 H 0.8609 0.4959 0.4637 0.035 Uiso 1 1 calc R U . . .
C15 C 0.8322(3) 0.3383(6) 0.4153(3) 0.0305(15) Uani 1 1 d . . . . .
H15 H 0.8696 0.3231 0.3950 0.037 Uiso 1 1 calc R U . . .
C16 C 0.7831(3) 0.2592(6) 0.4045(3) 0.0289(14) Uani 1 1 d . . . . .
H16 H 0.7878 0.1884 0.3778 0.035 Uiso 1 1 calc R U . . .
C17 C 0.7267(3) 0.2800(5) 0.4316(3) 0.0233(13) Uani 1 1 d . . . . .
H17 H 0.6930 0.2264 0.4224 0.028 Uiso 1 1 calc R U . . .
C18 C 0.7212(3) 0.3812(5) 0.4722(2) 0.0182(12) Uani 1 1 d . . . . .
C19 C 0.6731(2) 0.4273(5) 0.5124(2) 0.0192(12) Uani 1 1 d . . . . .
C20 C 0.5432(3) 0.2612(5) 0.4846(2) 0.0217(13) Uani 1 1 d . . . . .
C21 C 0.4397(3) 0.1462(7) 0.4383(3) 0.0381(16) Uani 1 1 d . . . . .
H21A H 0.4269 0.1348 0.4809 0.046 Uiso 1 1 calc R U . . .
H21B H 0.4236 0.2294 0.4236 0.046 Uiso 1 1 calc R U . . .
C22 C 0.4150(4) 0.0363(8) 0.3996(3) 0.0459(19) Uani 1 1 d . . . . .
H22A H 0.4289 0.0468 0.3578 0.069 Uiso 1 1 calc R U . . .
H22B H 0.3704 0.0374 0.4006 0.069 Uiso 1 1 calc R U . . .
H22C H 0.4297 -0.0459 0.4155 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
Pt1 N5 2.058(5) . ?
Pt1 N2 2.063(4) . ?
Pt1 S3 2.2569(15) . ?
Pt1 S1 2.2609(14) . ?
S1 C9 1.729(6) . ?
S2 C9 1.750(6) . ?
S2 C10 1.807(6) . ?
S3 C20 1.727(6) . ?
S4 C20 1.736(6) . ?
S4 C21 1.791(6) . ?
O1 C1 1.230(6) . ?
O2 C12 1.223(6) . ?
N1 C1 1.351(7) . ?
N1 C2 1.406(7) . ?
N1 H1 0.9099 . ?
N2 C8 1.302(7) . ?
N2 N3 1.389(6) . ?
N3 C9 1.303(7) . ?
N4 C12 1.359(7) . ?
N4 C13 1.403(7) . ?
N4 H4A 0.9100 . ?
N5 C19 1.308(7) . ?
N5 N6 1.373(6) . ?
N6 C20 1.321(7) . ?
C1 C8 1.514(7) . ?
C2 C3 1.390(8) . ?
C2 C7 1.396(7) . ?
C3 C4 1.395(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.386(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.461(7) . ?
C10 C11 1.520(9) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C19 1.505(7) . ?
C13 C14 1.381(8) . ?
C13 C18 1.409(8) . ?
C14 C15 1.398(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.379(9) . ?
C15 H15 0.9500 . ?
C16 C17 1.393(8) . ?
C16 H16 0.9500 . ?
C17 C18 1.389(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.463(7) . ?
C21 C22 1.528(10) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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
N5 Pt1 N2 102.04(18) . . ?
N5 Pt1 S3 82.45(14) . . ?
N2 Pt1 S3 167.61(13) . . ?
N5 Pt1 S1 170.42(13) . . ?
N2 Pt1 S1 82.04(13) . . ?
S3 Pt1 S1 95.37(6) . . ?
C9 S1 Pt1 95.66(19) . . ?
C9 S2 C10 104.9(3) . . ?
C20 S3 Pt1 95.19(19) . . ?
C20 S4 C21 103.4(3) . . ?
C1 N1 C2 110.2(5) . . ?
C1 N1 H1 122.4 . . ?
C2 N1 H1 127.0 . . ?
C8 N2 N3 114.2(4) . . ?
C8 N2 Pt1 128.4(4) . . ?
N3 N2 Pt1 117.4(3) . . ?
C9 N3 N2 113.1(4) . . ?
C12 N4 C13 111.6(5) . . ?
C12 N4 H4A 121.2 . . ?
C13 N4 H4A 126.8 . . ?
C19 N5 N6 114.3(5) . . ?
C19 N5 Pt1 127.1(4) . . ?
N6 N5 Pt1 118.4(3) . . ?
C20 N6 N5 112.3(5) . . ?
O1 C1 N1 125.9(5) . . ?
O1 C1 C8 127.8(5) . . ?
N1 C1 C8 106.2(5) . . ?
C3 C2 C7 123.0(5) . . ?
C3 C2 N1 125.7(5) . . ?
C7 C2 N1 111.3(5) . . ?
C2 C3 C4 115.7(5) . . ?
C2 C3 H3 122.1 . . ?
C4 C3 H3 122.1 . . ?
C5 C4 C3 121.7(5) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 122.0(5) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C7 C6 C5 117.0(5) . . ?
C7 C6 H6 121.5 . . ?
C5 C6 H6 121.5 . . ?
C6 C7 C2 120.5(5) . . ?
C6 C7 C8 134.2(5) . . ?
C2 C7 C8 105.3(5) . . ?
N2 C8 C7 130.0(5) . . ?
N2 C8 C1 123.6(5) . . ?
C7 C8 C1 106.3(5) . . ?
N3 C9 S1 124.9(4) . . ?
N3 C9 S2 112.5(4) . . ?
S1 C9 S2 122.5(3) . . ?
C11 C10 S2 115.3(5) . . ?
C11 C10 H10A 108.4 . . ?
S2 C10 H10A 108.4 . . ?
C11 C10 H10B 108.4 . . ?
S2 C10 H10B 108.4 . . ?
H10A C10 H10B 107.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 N4 126.2(5) . . ?
O2 C12 C19 128.1(5) . . ?
N4 C12 C19 105.6(5) . . ?
C14 C13 N4 127.9(5) . . ?
C14 C13 C18 122.2(5) . . ?
N4 C13 C18 109.9(5) . . ?
C13 C14 C15 117.7(6) . . ?
C13 C14 H14 121.1 . . ?
C15 C14 H14 121.1 . . ?
C16 C15 C14 120.4(6) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 122.1(6) . . ?
C15 C16 H16 119.0 . . ?
C17 C16 H16 119.0 . . ?
C18 C17 C16 118.2(6) . . ?
C18 C17 H17 120.9 . . ?
C16 C17 H17 120.9 . . ?
C17 C18 C13 119.4(5) . . ?
C17 C18 C19 134.8(5) . . ?
C13 C18 C19 105.7(5) . . ?
N5 C19 C18 129.4(5) . . ?
N5 C19 C12 123.6(5) . . ?
C18 C19 C12 106.9(5) . . ?
N6 C20 S3 125.4(4) . . ?
N6 C20 S4 112.6(4) . . ?
S3 C20 S4 121.9(3) . . ?
C22 C21 S4 108.1(5) . . ?
C22 C21 H21A 110.1 . . ?
S4 C21 H21A 110.1 . . ?
C22 C21 H21B 110.1 . . ?
S4 C21 H21B 110.1 . . ?
H21A C21 H21B 108.4 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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
C8 N2 N3 C9 -155.1(5) . . . . ?
Pt1 N2 N3 C9 23.1(6) . . . . ?
C19 N5 N6 C20 -164.0(5) . . . . ?
Pt1 N5 N6 C20 20.7(6) . . . . ?
C2 N1 C1 O1 -169.6(5) . . . . ?
C2 N1 C1 C8 7.5(6) . . . . ?
C1 N1 C2 C3 174.7(5) . . . . ?
C1 N1 C2 C7 -4.2(6) . . . . ?
C7 C2 C3 C4 0.4(8) . . . . ?
N1 C2 C3 C4 -178.3(5) . . . . ?
C2 C3 C4 C5 -1.3(9) . . . . ?
C3 C4 C5 C6 1.8(9) . . . . ?
C4 C5 C6 C7 -1.3(9) . . . . ?
C5 C6 C7 C2 0.4(8) . . . . ?
C5 C6 C7 C8 -179.3(6) . . . . ?
C3 C2 C7 C6 0.0(9) . . . . ?
N1 C2 C7 C6 179.0(5) . . . . ?
C3 C2 C7 C8 179.8(5) . . . . ?
N1 C2 C7 C8 -1.3(6) . . . . ?
N3 N2 C8 C7 -9.9(8) . . . . ?
Pt1 N2 C8 C7 172.1(4) . . . . ?
N3 N2 C8 C1 172.2(5) . . . . ?
Pt1 N2 C8 C1 -5.8(8) . . . . ?
C6 C7 C8 N2 7.2(10) . . . . ?
C2 C7 C8 N2 -172.5(5) . . . . ?
C6 C7 C8 C1 -174.7(6) . . . . ?
C2 C7 C8 C1 5.6(6) . . . . ?
O1 C1 C8 N2 -12.9(9) . . . . ?
N1 C1 C8 N2 170.1(5) . . . . ?
O1 C1 C8 C7 168.8(5) . . . . ?
N1 C1 C8 C7 -8.2(6) . . . . ?
N2 N3 C9 S1 -3.2(7) . . . . ?
N2 N3 C9 S2 174.2(4) . . . . ?
Pt1 S1 C9 N3 -14.4(5) . . . . ?
Pt1 S1 C9 S2 168.4(3) . . . . ?
C10 S2 C9 N3 -177.6(4) . . . . ?
C10 S2 C9 S1 -0.1(4) . . . . ?
C9 S2 C10 C11 -78.9(5) . . . . ?
C13 N4 C12 O2 -172.6(5) . . . . ?
C13 N4 C12 C19 5.3(6) . . . . ?
C12 N4 C13 C14 177.6(6) . . . . ?
C12 N4 C13 C18 -2.2(7) . . . . ?
N4 C13 C14 C15 177.8(6) . . . . ?
C18 C13 C14 C15 -2.4(9) . . . . ?
C13 C14 C15 C16 0.1(9) . . . . ?
C14 C15 C16 C17 2.3(9) . . . . ?
C15 C16 C17 C18 -2.3(9) . . . . ?
C16 C17 C18 C13 0.1(8) . . . . ?
C16 C17 C18 C19 -174.3(6) . . . . ?
C14 C13 C18 C17 2.3(9) . . . . ?
N4 C13 C18 C17 -177.8(5) . . . . ?
C14 C13 C18 C19 178.2(5) . . . . ?
N4 C13 C18 C19 -2.0(6) . . . . ?
N6 N5 C19 C18 -12.2(8) . . . . ?
Pt1 N5 C19 C18 162.6(4) . . . . ?
N6 N5 C19 C12 171.1(5) . . . . ?
Pt1 N5 C19 C12 -14.1(8) . . . . ?
C17 C18 C19 N5 2.8(11) . . . . ?
C13 C18 C19 N5 -172.2(6) . . . . ?
C17 C18 C19 C12 179.9(6) . . . . ?
C13 C18 C19 C12 5.0(6) . . . . ?
O2 C12 C19 N5 -11.2(9) . . . . ?
N4 C12 C19 N5 171.1(5) . . . . ?
O2 C12 C19 C18 171.5(6) . . . . ?
N4 C12 C19 C18 -6.3(6) . . . . ?
N5 N6 C20 S3 -1.1(7) . . . . ?
N5 N6 C20 S4 178.7(4) . . . . ?
Pt1 S3 C20 N6 -15.1(5) . . . . ?
Pt1 S3 C20 S4 165.1(3) . . . . ?
C21 S4 C20 N6 -173.0(5) . . . . ?
C21 S4 C20 S3 6.8(5) . . . . ?
C20 S4 C21 C22 -173.9(5) . . . . ?

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 O2 0.91 1.93 2.829(6) 169 8_755
N4 H4A O1 0.91 2.02 2.876(6) 157 8_765
C3 H3 S2 0.95 2.95 3.785(6) 147 8_755
C11 H11A S1 0.98 2.87 3.483(6) 121 .
C11 H11A S4 0.98 2.98 3.705(7) 132 5_666
C21 H21B O2 0.99 2.60 3.455(8) 145 5_666

_refine_diff_density_max         2.293
_refine_diff_density_min         -0.769
_refine_diff_density_rms         0.187

####################################################################### 
# 
# 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_JTM818_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc22grcp
_database_code_depnum_ccdc_archive 'CCDC 1920802'
loop_
_audit_author_name
_audit_author_address
'Joel T. Mague'
;Tulane University
United States of America
;
_audit_update_record             
;
2019-06-04 deposited with the CCDC.	2020-04-23 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         '2(C22 H20 N6 O2 S4), C2 H6 O'
_chemical_formula_sum            'C46 H46 N12 O5 S8'
_chemical_formula_weight         1103.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   8.4393(16)
_cell_length_b                   11.765(2)
_cell_length_c                   14.287(3)
_cell_angle_alpha                86.938(3)
_cell_angle_beta                 81.286(3)
_cell_angle_gamma                74.585(2)
_cell_volume                     1351.6(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3424
_cell_measurement_theta_min      2.2878
_cell_measurement_theta_max      28.0467
_cell_measurement_temperature    100(2)

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_F_000             574
_exptl_transmission_factor_min   0.573
_exptl_transmission_factor_max   0.862
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.386
_shelx_estimated_absorpt_T_min   0.930
_shelx_estimated_absorpt_T_max   0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_correction_T_min  0.63
_exptl_absorpt_correction_T_max  0.95

_exptl_special_details           
; 
The diffraction data were collected in three sets of 
363 frames (0.5° width in ω) at φ = 0, 120 
and 240°. A scan time of 60 sec/frame was used. 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker Smart APEX CCD'
_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            12852
_diffrn_reflns_av_unetI/netI     0.1153
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.442
_diffrn_reflns_theta_max         28.385
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             6523
_reflns_number_gt                4072
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2012)'
_computing_publication_material  'SHELXTL (Bruker, 2016)'

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. H-atoms attached to the 
methyl carbon atoms and those of the lattice solvent were placed in 
calculated positions (C---H = 0.98 - 0.99 Å) while that attached to oxygen 
was placed using an AFIX 147 instruction. All were included as riding 
contributions with isotropic displacement parameters 1.2 - 1.5 times those 
of the attached atoms.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0693P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6523
_refine_ls_number_parameters     394
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1036
_refine_ls_R_factor_gt           0.0624
_refine_ls_wR_factor_ref         0.1702
_refine_ls_wR_factor_gt          0.1506
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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
S1 S 0.64480(10) 0.29601(7) 0.13349(6) 0.0279(2) Uani 1 1 d . . . . .
S2 S 0.42541(10) 0.52360(7) 0.21976(6) 0.0275(2) Uani 1 1 d . . . . .
S3 S 0.35026(10) 0.38940(7) 0.29484(6) 0.0278(2) Uani 1 1 d . . . . .
S4 S 0.63228(10) 0.42943(7) 0.38632(6) 0.0278(2) Uani 1 1 d . . . . .
O1 O 0.4480(3) 0.87960(18) 0.07739(16) 0.0279(5) Uani 1 1 d . . . . .
O2 O 0.0688(3) 0.1186(2) 0.42285(16) 0.0336(6) Uani 1 1 d . . . . .
N1 N 0.6445(3) 0.8721(2) -0.05440(19) 0.0242(6) Uani 1 1 d . . . . .
H1A H 0.627(5) 0.943(4) -0.063(3) 0.047(12) Uiso 1 1 d . . . . .
N2 N 0.5782(3) 0.6280(2) 0.07856(18) 0.0242(6) Uani 1 1 d . . . . .
N3 N 0.6520(3) 0.5077(2) 0.06562(18) 0.0246(6) Uani 1 1 d . . . . .
N4 N 0.1646(4) 0.0154(2) 0.5532(2) 0.0298(7) Uani 1 1 d . . . . .
H4A H 0.092(5) -0.031(3) 0.567(3) 0.045(11) Uiso 1 1 d . . . . .
N5 N 0.3254(3) 0.2362(2) 0.43436(19) 0.0283(6) Uani 1 1 d . . . . .
N6 N 0.4541(3) 0.2813(2) 0.45079(19) 0.0274(6) Uani 1 1 d . . . . .
C1 C 0.6395(4) 0.6937(3) 0.0166(2) 0.0219(7) Uani 1 1 d . . . . .
C2 C 0.7685(4) 0.6737(3) -0.0650(2) 0.0228(7) Uani 1 1 d . . . . .
C3 C 0.8838(4) 0.5734(3) -0.1054(2) 0.0264(7) Uani 1 1 d . . . . .
H3 H 0.888(4) 0.508(3) -0.077(2) 0.024(9) Uiso 1 1 d . . . . .
C4 C 0.9900(4) 0.5879(3) -0.1859(2) 0.0271(7) Uani 1 1 d . . . . .
H4 H 1.067(4) 0.527(3) -0.215(2) 0.029(9) Uiso 1 1 d . . . . .
C5 C 0.9829(4) 0.6980(3) -0.2271(2) 0.0276(7) Uani 1 1 d . . . . .
H5 H 1.055(4) 0.708(3) -0.282(2) 0.020(8) Uiso 1 1 d . . . . .
C6 C 0.8703(4) 0.7988(3) -0.1887(2) 0.0266(7) Uani 1 1 d . . . . .
H6 H 0.871(4) 0.874(3) -0.213(2) 0.036(10) Uiso 1 1 d . . . . .
C7 C 0.7673(4) 0.7845(3) -0.1069(2) 0.0221(7) Uani 1 1 d . . . . .
C8 C 0.5627(4) 0.8255(3) 0.0201(2) 0.0257(7) Uani 1 1 d . . . . .
C9 C 0.5836(4) 0.4476(3) 0.1308(2) 0.0240(7) Uani 1 1 d . . . . .
C10 C 0.8041(4) 0.2678(3) 0.0319(3) 0.0292(8) Uani 1 1 d . . . . .
H10A H 0.881(4) 0.307(3) 0.039(2) 0.025(9) Uiso 1 1 d . . . . .
H10B H 0.754(4) 0.295(3) -0.025(2) 0.027(9) Uiso 1 1 d . . . . .
C11 C 0.8816(5) 0.1356(3) 0.0272(3) 0.0418(10) Uani 1 1 d . . . . .
H11A H 0.926934 0.107905 0.085999 0.063 Uiso 1 1 calc R U . . .
H11B H 0.971146 0.118222 -0.026552 0.063 Uiso 1 1 calc R U . . .
H11C H 0.796883 0.095341 0.019041 0.063 Uiso 1 1 calc R U . . .
C12 C 0.2977(4) 0.1557(3) 0.4937(2) 0.0267(7) Uani 1 1 d . . . . .
C13 C 0.3710(4) 0.1010(3) 0.5773(2) 0.0265(7) Uani 1 1 d . . . . .
C14 C 0.4937(4) 0.1173(3) 0.6238(2) 0.0314(8) Uani 1 1 d . . . . .
H14 H 0.562(4) 0.169(3) 0.604(2) 0.034(10) Uiso 1 1 d . . . . .
C15 C 0.5309(5) 0.0487(4) 0.7042(3) 0.0411(9) Uani 1 1 d . . . . .
H15 H 0.622(5) 0.060(3) 0.734(2) 0.041(11) Uiso 1 1 d . . . . .
C16 C 0.4462(5) -0.0349(3) 0.7355(3) 0.0402(9) Uani 1 1 d . . . . .
H16 H 0.469(5) -0.081(3) 0.791(3) 0.050(11) Uiso 1 1 d . . . . .
C17 C 0.3208(4) -0.0522(3) 0.6894(3) 0.0333(8) Uani 1 1 d . . . . .
H17 H 0.268(4) -0.107(3) 0.709(2) 0.030(9) Uiso 1 1 d . . . . .
C18 C 0.2848(4) 0.0165(3) 0.6107(2) 0.0264(7) Uani 1 1 d . . . . .
C19 C 0.1625(4) 0.0974(3) 0.4825(2) 0.0294(8) Uani 1 1 d . . . . .
C20 C 0.4790(4) 0.3577(3) 0.3860(2) 0.0236(7) Uani 1 1 d . . . . .
C21 C 0.7331(4) 0.3548(3) 0.4844(3) 0.0315(8) Uani 1 1 d . . . . .
H21A H 0.654(4) 0.364(3) 0.538(2) 0.032(10) Uiso 1 1 d . . . . .
H21B H 0.777(4) 0.267(3) 0.470(2) 0.029(9) Uiso 1 1 d . . . . .
C22 C 0.8767(4) 0.4056(3) 0.4930(3) 0.0371(9) Uani 1 1 d . . . . .
H22A H 0.959211 0.387234 0.436035 0.056 Uiso 1 1 calc R U . . .
H22B H 0.927839 0.371151 0.548683 0.056 Uiso 1 1 calc R U . . .
H22C H 0.836311 0.491293 0.499745 0.056 Uiso 1 1 calc R U . . .
O3 O -0.1388(7) 0.1022(5) 0.8006(4) 0.0497(14) Uani 0.5 1 d . . P . .
H3A H -0.222514 0.130950 0.840176 0.075 Uiso 0.5 1 calc R U P . .
C23 C -0.1083(10) 0.1890(6) 0.7368(6) 0.0431(19) Uani 0.5 1 d . . P . .
H23A H -0.214945 0.247408 0.730306 0.052 Uiso 0.5 1 calc R U P . .
H23B H -0.062761 0.152845 0.674136 0.052 Uiso 0.5 1 calc R U P . .
C24 C 0.0103(12) 0.2522(7) 0.7644(7) 0.065(3) Uani 0.5 1 d . . P . .
H24A H 0.102411 0.195021 0.789020 0.097 Uiso 0.5 1 calc R U P . .
H24B H -0.047877 0.309885 0.813339 0.097 Uiso 0.5 1 calc R U P . .
H24C H 0.053790 0.292950 0.708751 0.097 Uiso 0.5 1 calc R U 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
S1 C9 1.720(3) . ?
S1 C10 1.802(4) . ?
S2 C9 1.781(3) . ?
S2 S3 2.0471(11) . ?
S3 C20 1.783(3) . ?
S4 C20 1.722(3) . ?
S4 C21 1.815(4) . ?
O1 C8 1.225(4) . ?
O2 C19 1.221(4) . ?
N1 C8 1.352(4) . ?
N1 C7 1.407(4) . ?
N1 H1A 0.81(4) . ?
N2 C1 1.284(4) . ?
N2 N3 1.396(3) . ?
N3 C9 1.297(4) . ?
N4 C19 1.358(4) . ?
N4 C18 1.401(4) . ?
N4 H4A 0.92(4) . ?
N5 C12 1.281(4) . ?
N5 N6 1.384(4) . ?
N6 C20 1.289(4) . ?
C1 C2 1.451(4) . ?
C1 C8 1.514(4) . ?
C2 C3 1.402(4) . ?
C2 C7 1.403(4) . ?
C3 C4 1.380(5) . ?
C3 H3 0.84(3) . ?
C4 C5 1.385(4) . ?
C4 H4 0.90(3) . ?
C5 C6 1.387(5) . ?
C5 H5 0.94(3) . ?
C6 C7 1.378(4) . ?
C6 H6 0.93(3) . ?
C10 C11 1.519(4) . ?
C10 H10A 0.91(3) . ?
C10 H10B 0.97(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.467(4) . ?
C12 C19 1.511(4) . ?
C13 C14 1.371(5) . ?
C13 C18 1.405(4) . ?
C14 C15 1.394(5) . ?
C14 H14 0.96(3) . ?
C15 C16 1.382(5) . ?
C15 H15 0.97(4) . ?
C16 C17 1.390(5) . ?
C16 H16 0.96(4) . ?
C17 C18 1.374(4) . ?
C17 H17 0.88(3) . ?
C21 C22 1.509(5) . ?
C21 H21A 0.93(3) . ?
C21 H21B 1.02(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
O3 C23 1.381(9) . ?
O3 H3A 0.8400 . ?
C23 C24 1.502(12) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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
C9 S1 C10 100.78(16) . . ?
C9 S2 S3 102.89(11) . . ?
C20 S3 S2 103.04(11) . . ?
C20 S4 C21 100.94(16) . . ?
C8 N1 C7 111.7(3) . . ?
C8 N1 H1A 122(3) . . ?
C7 N1 H1A 127(3) . . ?
C1 N2 N3 113.5(2) . . ?
C9 N3 N2 109.7(3) . . ?
C19 N4 C18 111.3(3) . . ?
C19 N4 H4A 126(2) . . ?
C18 N4 H4A 122(2) . . ?
C12 N5 N6 113.9(3) . . ?
C20 N6 N5 110.3(3) . . ?
N2 C1 C2 135.5(3) . . ?
N2 C1 C8 118.2(3) . . ?
C2 C1 C8 106.2(2) . . ?
C3 C2 C7 119.0(3) . . ?
C3 C2 C1 134.3(3) . . ?
C7 C2 C1 106.8(3) . . ?
C4 C3 C2 118.3(3) . . ?
C4 C3 H3 124(2) . . ?
C2 C3 H3 118(2) . . ?
C3 C4 C5 121.4(3) . . ?
C3 C4 H4 122(2) . . ?
C5 C4 H4 116(2) . . ?
C4 C5 C6 121.5(3) . . ?
C4 C5 H5 121.3(19) . . ?
C6 C5 H5 117.2(19) . . ?
C7 C6 C5 116.9(3) . . ?
C7 C6 H6 121(2) . . ?
C5 C6 H6 122(2) . . ?
C6 C7 C2 122.8(3) . . ?
C6 C7 N1 127.8(3) . . ?
C2 C7 N1 109.4(3) . . ?
O1 C8 N1 126.5(3) . . ?
O1 C8 C1 127.5(3) . . ?
N1 C8 C1 105.9(3) . . ?
N3 C9 S1 121.2(2) . . ?
N3 C9 S2 119.3(2) . . ?
S1 C9 S2 119.47(18) . . ?
C11 C10 S1 108.0(3) . . ?
C11 C10 H10A 111(2) . . ?
S1 C10 H10A 108(2) . . ?
C11 C10 H10B 110.1(19) . . ?
S1 C10 H10B 109.0(19) . . ?
H10A C10 H10B 111(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N5 C12 C13 134.2(3) . . ?
N5 C12 C19 119.2(3) . . ?
C13 C12 C19 106.6(3) . . ?
C14 C13 C18 120.2(3) . . ?
C14 C13 C12 134.2(3) . . ?
C18 C13 C12 105.6(3) . . ?
C13 C14 C15 118.8(3) . . ?
C13 C14 H14 126(2) . . ?
C15 C14 H14 116(2) . . ?
C16 C15 C14 120.3(4) . . ?
C16 C15 H15 123(2) . . ?
C14 C15 H15 117(2) . . ?
C15 C16 C17 121.6(3) . . ?
C15 C16 H16 121(2) . . ?
C17 C16 H16 117(2) . . ?
C18 C17 C16 117.5(3) . . ?
C18 C17 H17 121(2) . . ?
C16 C17 H17 121(2) . . ?
C17 C18 N4 127.8(3) . . ?
C17 C18 C13 121.6(3) . . ?
N4 C18 C13 110.5(3) . . ?
O2 C19 N4 126.1(3) . . ?
O2 C19 C12 127.9(3) . . ?
N4 C19 C12 106.0(3) . . ?
N6 C20 S4 121.5(2) . . ?
N6 C20 S3 118.7(2) . . ?
S4 C20 S3 119.83(18) . . ?
C22 C21 S4 107.9(3) . . ?
C22 C21 H21A 114(2) . . ?
S4 C21 H21A 108(2) . . ?
C22 C21 H21B 109.2(19) . . ?
S4 C21 H21B 108.6(18) . . ?
H21A C21 H21B 109(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C23 O3 H3A 109.5 . . ?
O3 C23 C24 113.9(7) . . ?
O3 C23 H23A 108.8 . . ?
C24 C23 H23A 108.8 . . ?
O3 C23 H23B 108.8 . . ?
C24 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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 C9 179.9(3) . . . . ?
C12 N5 N6 C20 177.2(3) . . . . ?
N3 N2 C1 C2 0.0(5) . . . . ?
N3 N2 C1 C8 176.6(2) . . . . ?
N2 C1 C2 C3 -4.1(6) . . . . ?
C8 C1 C2 C3 179.1(3) . . . . ?
N2 C1 C2 C7 176.4(3) . . . . ?
C8 C1 C2 C7 -0.5(3) . . . . ?
C7 C2 C3 C4 -1.0(5) . . . . ?
C1 C2 C3 C4 179.5(3) . . . . ?
C2 C3 C4 C5 -0.7(5) . . . . ?
C3 C4 C5 C6 0.8(5) . . . . ?
C4 C5 C6 C7 0.8(5) . . . . ?
C5 C6 C7 C2 -2.6(5) . . . . ?
C5 C6 C7 N1 179.6(3) . . . . ?
C3 C2 C7 C6 2.7(5) . . . . ?
C1 C2 C7 C6 -177.6(3) . . . . ?
C3 C2 C7 N1 -179.1(3) . . . . ?
C1 C2 C7 N1 0.6(3) . . . . ?
C8 N1 C7 C6 177.6(3) . . . . ?
C8 N1 C7 C2 -0.4(4) . . . . ?
C7 N1 C8 O1 -178.7(3) . . . . ?
C7 N1 C8 C1 0.1(3) . . . . ?
N2 C1 C8 O1 1.6(5) . . . . ?
C2 C1 C8 O1 179.0(3) . . . . ?
N2 C1 C8 N1 -177.3(3) . . . . ?
C2 C1 C8 N1 0.2(3) . . . . ?
N2 N3 C9 S1 179.0(2) . . . . ?
N2 N3 C9 S2 -1.8(3) . . . . ?
C10 S1 C9 N3 0.1(3) . . . . ?
C10 S1 C9 S2 -179.2(2) . . . . ?
S3 S2 C9 N3 175.4(2) . . . . ?
S3 S2 C9 S1 -5.3(2) . . . . ?
C9 S1 C10 C11 176.2(2) . . . . ?
N6 N5 C12 C13 1.2(5) . . . . ?
N6 N5 C12 C19 -178.8(3) . . . . ?
N5 C12 C13 C14 1.5(7) . . . . ?
C19 C12 C13 C14 -178.5(4) . . . . ?
N5 C12 C13 C18 -179.4(4) . . . . ?
C19 C12 C13 C18 0.6(4) . . . . ?
C18 C13 C14 C15 0.1(5) . . . . ?
C12 C13 C14 C15 179.1(4) . . . . ?
C13 C14 C15 C16 0.6(6) . . . . ?
C14 C15 C16 C17 -1.0(7) . . . . ?
C15 C16 C17 C18 0.6(6) . . . . ?
C16 C17 C18 N4 -179.9(3) . . . . ?
C16 C17 C18 C13 0.1(5) . . . . ?
C19 N4 C18 C17 178.9(3) . . . . ?
C19 N4 C18 C13 -1.1(4) . . . . ?
C14 C13 C18 C17 -0.5(5) . . . . ?
C12 C13 C18 C17 -179.8(3) . . . . ?
C14 C13 C18 N4 179.5(3) . . . . ?
C12 C13 C18 N4 0.2(4) . . . . ?
C18 N4 C19 O2 -178.3(3) . . . . ?
C18 N4 C19 C12 1.5(4) . . . . ?
N5 C12 C19 O2 -1.5(6) . . . . ?
C13 C12 C19 O2 178.5(3) . . . . ?
N5 C12 C19 N4 178.7(3) . . . . ?
C13 C12 C19 N4 -1.3(4) . . . . ?
N5 N6 C20 S4 -179.7(2) . . . . ?
N5 N6 C20 S3 0.6(4) . . . . ?
C21 S4 C20 N6 5.5(3) . . . . ?
C21 S4 C20 S3 -174.81(19) . . . . ?
S2 S3 C20 N6 175.1(2) . . . . ?
S2 S3 C20 S4 -4.7(2) . . . . ?
C20 S4 C21 C22 178.4(2) . . . . ?

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 O1 0.81(4) 2.03(4) 2.831(3) 172(4) 2_675
N4 H4A O2 0.92(4) 1.90(4) 2.805(3) 171(3) 2_556
C11 H11C O1 0.98 2.60 3.400(4) 139 2_665
C21 H21B O2 1.02(3) 2.63(3) 3.442(4) 137(2) 1_655
O3 H3A O1 0.84 2.11 2.874(6) 151 2_566
C23 H23A S2 0.99 2.86 3.727(7) 146 2_566
C23 H23B N4 0.99 2.63 3.549(8) 154 .

_refine_diff_density_max         0.676
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.095

####################################################################### 
# 
# 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_JTM770_0m
_audit_block_doi                 10.5517/ccdc.csd.cc22grdq
_database_code_depnum_ccdc_archive 'CCDC 1920803'
loop_
_audit_author_name
_audit_author_address
'Joel T. Mague'
;Tulane University
United States of America
;
_audit_update_record             
;
2019-06-04 deposited with the CCDC.	2020-04-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(3Z)-3-({[(ethylsulfanyl)methanethioyl]amino}imino)-2,3-dihydro-1H-indole-2-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H11 N3 O S2'
_chemical_formula_sum            'C11 H11 N3 O S2'
_chemical_formula_weight         265.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   4.5172(2)
_cell_length_b                   13.5286(5)
_cell_length_c                   19.8833(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1215.10(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8771
_cell_measurement_theta_min      3.9522
_cell_measurement_theta_max      72.3440
_cell_measurement_temperature    150(2)

_exptl_crystal_description       column
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   0.673
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.208
_exptl_crystal_size_mid          0.093
_exptl_crystal_size_min          0.056
_exptl_absorpt_coefficient_mu    3.871
_shelx_estimated_absorpt_T_min   0.500
_shelx_estimated_absorpt_T_max   0.812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_correction_T_min  0.63
_exptl_absorpt_correction_T_max  0.81

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'INCOATEC I\mS micro--focus source'
_diffrn_radiation_monochromator  mirror

_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            9302
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.952
_diffrn_reflns_theta_max         72.337
_diffrn_reflns_theta_full        72.300
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2384
_reflns_number_gt                2302
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.667
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.995

_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT  (Bruker, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  
'SHELXL 2014/7 (Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2012)'
_computing_publication_material  'SHELXTL (Bruker, 2016)'

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. 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)+(0.0813P)²+0.5441P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.40(3)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2384
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1173
_refine_ls_wR_factor_gt          0.1162
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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
S1 S 1.2259(2) 0.51658(7) 0.72127(5) 0.0320(3) Uani 1 1 d . . . . .
S2 S 0.9829(2) 0.32410(6) 0.66424(4) 0.0242(3) Uani 1 1 d . . . . .
O1 O 0.6734(7) 0.67193(19) 0.56100(13) 0.0286(6) Uani 1 1 d . . . . .
N1 N 0.3252(8) 0.6329(2) 0.47979(16) 0.0241(7) Uani 1 1 d . . . . .
H1 H 0.278(10) 0.698(3) 0.468(2) 0.022(11) Uiso 1 1 d . . . . .
N2 N 0.6783(7) 0.4496(2) 0.57894(15) 0.0212(6) Uani 1 1 d . . . . .
N3 N 0.8577(8) 0.5004(2) 0.62085(16) 0.0235(7) Uani 1 1 d . . . . .
H3A H 0.846(13) 0.567(4) 0.618(3) 0.040(15) Uiso 1 1 d . . . . .
C1 C 0.5203(9) 0.6124(2) 0.52858(16) 0.0214(7) Uani 1 1 d . . . . .
C2 C 0.1968(8) 0.5457(3) 0.45414(17) 0.0197(7) Uani 1 1 d . . . . .
C3 C -0.0110(9) 0.5367(3) 0.40332(18) 0.0247(7) Uani 1 1 d . . . . .
H3 H -0.083(14) 0.596(4) 0.383(3) 0.055(18) Uiso 1 1 d . . . . .
C4 C -0.0994(9) 0.4414(3) 0.3862(2) 0.0281(9) Uani 1 1 d . . . . .
H4 H -0.249(13) 0.435(4) 0.347(3) 0.041(14) Uiso 1 1 d . . . . .
C5 C 0.0134(10) 0.3592(3) 0.41890(19) 0.0276(8) Uani 1 1 d . . . . .
H5 H -0.051(15) 0.293(5) 0.404(3) 0.062(19) Uiso 1 1 d . . . . .
C6 C 0.2219(9) 0.3690(3) 0.46984(19) 0.0238(8) Uani 1 1 d . . . . .
H6 H 0.306(11) 0.310(3) 0.490(2) 0.028(12) Uiso 1 1 d . . . . .
C7 C 0.3130(8) 0.4634(3) 0.48755(17) 0.0203(7) Uani 1 1 d . . . . .
C8 C 0.5205(9) 0.5014(2) 0.53673(16) 0.0197(7) Uani 1 1 d . . . . .
C9 C 1.0174(9) 0.4525(3) 0.66852(16) 0.0229(7) Uani 1 1 d . . . . .
C10 C 1.2007(10) 0.2847(3) 0.7357(2) 0.0304(9) Uani 1 1 d . . . . .
H10A H 1.194(16) 0.216(5) 0.726(3) 0.07(2) Uiso 1 1 d . . . . .
H10B H 1.397(11) 0.324(4) 0.734(2) 0.027(11) Uiso 1 1 d . . . . .
C11 C 1.0354(13) 0.2923(3) 0.8017(2) 0.0365(10) Uani 1 1 d . . . . .
H11A H 0.961(12) 0.361(4) 0.812(2) 0.034(13) Uiso 1 1 d . . . . .
H11B H 1.189(13) 0.269(4) 0.836(3) 0.043(15) Uiso 1 1 d . . . . .
H11C H 0.854(14) 0.254(4) 0.799(3) 0.041(14) 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
S1 C9 1.655(4) . ?
S2 C9 1.747(4) . ?
S2 C10 1.808(4) . ?
O1 C1 1.242(5) . ?
N1 C1 1.340(5) . ?
N1 C2 1.410(5) . ?
N1 H1 0.94(5) . ?
N2 C8 1.305(5) . ?
N2 N3 1.351(5) . ?
N3 C9 1.356(5) . ?
N3 H3A 0.90(5) . ?
C1 C8 1.511(4) . ?
C2 C3 1.384(5) . ?
C2 C7 1.398(5) . ?
C3 C4 1.391(6) . ?
C3 H3 0.96(6) . ?
C4 C5 1.385(6) . ?
C4 H4 1.03(6) . ?
C5 C6 1.390(6) . ?
C5 H5 0.99(6) . ?
C6 C7 1.388(5) . ?
C6 H6 0.97(5) . ?
C7 C8 1.448(5) . ?
C10 C11 1.513(6) . ?
C10 H10A 0.95(7) . ?
C10 H10B 1.03(5) . ?
C11 H11A 1.00(6) . ?
C11 H11B 1.02(6) . ?
C11 H11C 0.97(6) . ?

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
C9 S2 C10 101.92(19) . . ?
C1 N1 C2 111.0(3) . . ?
C1 N1 H1 122(3) . . ?
C2 N1 H1 127(3) . . ?
C8 N2 N3 116.8(3) . . ?
N2 N3 C9 120.5(3) . . ?
N2 N3 H3A 116(4) . . ?
C9 N3 H3A 123(4) . . ?
O1 C1 N1 127.4(3) . . ?
O1 C1 C8 126.1(3) . . ?
N1 C1 C8 106.5(3) . . ?
C3 C2 C7 122.1(3) . . ?
C3 C2 N1 128.1(3) . . ?
C7 C2 N1 109.8(3) . . ?
C2 C3 C4 117.0(3) . . ?
C2 C3 H3 118(4) . . ?
C4 C3 H3 125(4) . . ?
C5 C4 C3 121.6(4) . . ?
C5 C4 H4 121(3) . . ?
C3 C4 H4 117(3) . . ?
C4 C5 C6 121.0(4) . . ?
C4 C5 H5 119(4) . . ?
C6 C5 H5 120(4) . . ?
C7 C6 C5 118.3(4) . . ?
C7 C6 H6 123(3) . . ?
C5 C6 H6 119(3) . . ?
C6 C7 C2 120.0(3) . . ?
C6 C7 C8 133.6(3) . . ?
C2 C7 C8 106.4(3) . . ?
N2 C8 C7 126.7(3) . . ?
N2 C8 C1 127.1(3) . . ?
C7 C8 C1 106.2(3) . . ?
N3 C9 S1 119.7(3) . . ?
N3 C9 S2 113.2(3) . . ?
S1 C9 S2 127.1(2) . . ?
C11 C10 S2 113.1(3) . . ?
C11 C10 H10A 104(4) . . ?
S2 C10 H10A 96(4) . . ?
C11 C10 H10B 115(3) . . ?
S2 C10 H10B 107(3) . . ?
H10A C10 H10B 121(5) . . ?
C10 C11 H11A 113(3) . . ?
C10 C11 H11B 103(3) . . ?
H11A C11 H11B 112(4) . . ?
C10 C11 H11C 110(3) . . ?
H11A C11 H11C 103(5) . . ?
H11B C11 H11C 116(5) . . ?

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
C8 N2 N3 C9 176.6(3) . . . . ?
C2 N1 C1 O1 179.2(4) . . . . ?
C2 N1 C1 C8 -0.5(4) . . . . ?
C1 N1 C2 C3 -179.4(4) . . . . ?
C1 N1 C2 C7 -0.1(4) . . . . ?
C7 C2 C3 C4 -0.4(6) . . . . ?
N1 C2 C3 C4 178.8(4) . . . . ?
C2 C3 C4 C5 0.5(6) . . . . ?
C3 C4 C5 C6 -0.6(6) . . . . ?
C4 C5 C6 C7 0.5(6) . . . . ?
C5 C6 C7 C2 -0.4(6) . . . . ?
C5 C6 C7 C8 -179.9(4) . . . . ?
C3 C2 C7 C6 0.4(6) . . . . ?
N1 C2 C7 C6 -179.0(4) . . . . ?
C3 C2 C7 C8 -180.0(3) . . . . ?
N1 C2 C7 C8 0.7(4) . . . . ?
N3 N2 C8 C7 -179.7(3) . . . . ?
N3 N2 C8 C1 1.3(5) . . . . ?
C6 C7 C8 N2 -0.6(7) . . . . ?
C2 C7 C8 N2 179.8(4) . . . . ?
C6 C7 C8 C1 178.6(4) . . . . ?
C2 C7 C8 C1 -1.0(4) . . . . ?
O1 C1 C8 N2 0.4(6) . . . . ?
N1 C1 C8 N2 -179.9(4) . . . . ?
O1 C1 C8 C7 -178.8(4) . . . . ?
N1 C1 C8 C7 0.9(4) . . . . ?
N2 N3 C9 S1 -177.7(3) . . . . ?
N2 N3 C9 S2 4.3(4) . . . . ?
C10 S2 C9 N3 -177.0(3) . . . . ?
C10 S2 C9 S1 5.2(3) . . . . ?
C9 S2 C10 C11 80.6(4) . . . . ?

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 O1 0.94(5) 1.91(5) 2.846(4) 177(4) 4_466
N3 H3A O1 0.90(5) 1.98(5) 2.737(4) 140(5) .
C11 H11B O1 1.02(6) 2.51(5) 3.440(5) 151(4) 3_746

_refine_diff_density_max         1.406
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.101

####################################################################### 
# 
# 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_JTM773_0ma
_audit_block_doi                 10.5517/ccdc.csd.cc22grgs
_database_code_depnum_ccdc_archive 'CCDC 1920805'
loop_
_audit_author_name
_audit_author_address
'Joel T. Mague'
;Tulane University
United States of America
;
_audit_update_record             
;
2019-06-04 deposited with the CCDC.	2020-04-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 Co N6 O2 S4'
_chemical_formula_sum            'C22 H20 Co N6 O2 S4'
_chemical_formula_weight         587.61

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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'

_cell_length_a                   15.820(4)
_cell_length_b                   15.920(4)
_cell_length_c                   10.324(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.978(3)
_cell_angle_gamma                90
_cell_volume                     2459.0(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6145
_cell_measurement_theta_min      2.4472
_cell_measurement_theta_max      28.0080
_cell_measurement_temperature    100(2)

_exptl_crystal_description       column
_exptl_crystal_colour            'dark orange'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_F_000             1204
_exptl_transmission_factor_min   0.758
_exptl_transmission_factor_max   0.928
_exptl_crystal_size_max          0.157
_exptl_crystal_size_mid          0.088
_exptl_crystal_size_min          0.075
_exptl_absorpt_coefficient_mu    1.071
_shelx_estimated_absorpt_T_min   0.850
_shelx_estimated_absorpt_T_max   0.924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_T_max  0.92

_exptl_special_details           
;
The diffraction data were collected in three sets of 
363 frames (0.5° width in ω) at φ = 0, 120 
and 240°. A scan time of 60 sec/frame was used. 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker Smart APEX CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            23075
_diffrn_reflns_av_unetI/netI     0.0625
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.361
_diffrn_reflns_theta_max         28.879
_diffrn_reflns_theta_full        28.000
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             6183
_reflns_number_gt                4490
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2012)'
_computing_publication_material  'SHELXTL (Bruker, 2016)'

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. H-atoms attached to carbon 
were placed in calculated positions (C---H = 0.95 - 0.99 Å) while those 
attached to nitrogen were placed in locations derived from a difference 
map and their coordinates adjusted to give N---H = 0.91 %A. All were included 
as riding contributions with isotropic displacement parameters 1.2 - 1.5 
times those of the attached atoms.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0525P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6183
_refine_ls_number_parameters     318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1018
_refine_ls_wR_factor_gt          0.0942
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_restrained_S_all      0.987
_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 0.74322(2) 0.55427(2) 0.72081(3) 0.01636(9) Uani 1 1 d . . . . .
S1 S 0.70172(4) 0.46787(4) 0.87576(6) 0.02076(14) Uani 1 1 d . . . . .
S2 S 0.52348(4) 0.42324(4) 0.87199(6) 0.02162(14) Uani 1 1 d . . . . .
S3 S 0.79687(4) 0.45554(4) 0.59424(6) 0.02043(14) Uani 1 1 d . . . . .
S4 S 0.97987(4) 0.39787(4) 0.65119(6) 0.02341(14) Uani 1 1 d . . . . .
O1 O 0.73250(10) 0.65448(9) 0.56376(16) 0.0208(3) Uani 1 1 d . . . . .
O2 O 0.74645(9) 0.67333(9) 0.84915(16) 0.0202(3) Uani 1 1 d . . . . .
N1 N 0.61385(12) 0.73712(11) 0.43112(19) 0.0181(4) Uani 1 1 d . . . . .
H1 H 0.6442 0.7725 0.3927 0.022 Uiso 1 1 d R U . . .
N2 N 0.60665(12) 0.57182(11) 0.64529(18) 0.0160(4) Uani 1 1 d . . . . .
N3 N 0.54670(12) 0.53162(11) 0.69303(19) 0.0155(4) Uani 1 1 d . . . . .
N4 N 0.86397(12) 0.74898(11) 1.00036(19) 0.0182(4) Uani 1 1 d . . . . .
H4A H 0.8289 0.7852 1.0284 0.022 Uiso 1 1 d R U . . .
N5 N 0.87837(12) 0.57396(11) 0.80890(18) 0.0153(4) Uani 1 1 d . . . . .
N6 N 0.94300(12) 0.52544(11) 0.78655(19) 0.0154(4) Uani 1 1 d . . . . .
C1 C 0.65206(15) 0.67451(13) 0.5183(2) 0.0173(5) Uani 1 1 d . . . . .
C2 C 0.52055(14) 0.74009(13) 0.4085(2) 0.0165(5) Uani 1 1 d . . . . .
C3 C 0.45916(15) 0.79569(14) 0.3285(2) 0.0203(5) Uani 1 1 d . . . . .
H3 H 0.4761 0.8392 0.2789 0.024 Uiso 1 1 calc R U . . .
C4 C 0.37035(15) 0.78511(14) 0.3236(2) 0.0229(5) Uani 1 1 d . . . . .
H4 H 0.3262 0.8228 0.2701 0.028 Uiso 1 1 calc R U . . .
C5 C 0.34483(15) 0.72151(14) 0.3943(2) 0.0228(5) Uani 1 1 d . . . . .
H5 H 0.2837 0.7160 0.3875 0.027 Uiso 1 1 calc R U . . .
C6 C 0.40791(14) 0.66499(14) 0.4759(2) 0.0182(5) Uani 1 1 d . . . . .
H6 H 0.3905 0.6212 0.5245 0.022 Uiso 1 1 calc R U . . .
C7 C 0.49685(14) 0.67510(13) 0.4834(2) 0.0163(4) Uani 1 1 d . . . . .
C8 C 0.57934(14) 0.63181(13) 0.5558(2) 0.0164(4) Uani 1 1 d . . . . .
C9 C 0.58838(14) 0.48195(13) 0.7981(2) 0.0168(4) Uani 1 1 d . . . . .
C10 C 0.40925(15) 0.45260(14) 0.7750(3) 0.0230(5) Uani 1 1 d . . . . .
H10A H 0.3977 0.5115 0.7951 0.028 Uiso 1 1 calc R U . . .
H10B H 0.3991 0.4474 0.6756 0.028 Uiso 1 1 calc R U . . .
C11 C 0.34720(16) 0.39343(15) 0.8177(3) 0.0292(6) Uani 1 1 d . . . . .
H11A H 0.2858 0.4007 0.7559 0.044 Uiso 1 1 calc R U . . .
H11B H 0.3498 0.4063 0.9118 0.044 Uiso 1 1 calc R U . . .
H11C H 0.3661 0.3352 0.8129 0.044 Uiso 1 1 calc R U . . .
C12 C 0.82705(14) 0.68733(13) 0.9093(2) 0.0177(5) Uani 1 1 d . . . . .
C13 C 0.95821(14) 0.74220(13) 1.0466(2) 0.0162(4) Uani 1 1 d . . . . .
C14 C 1.01940(14) 0.79122(13) 1.1429(2) 0.0177(5) Uani 1 1 d . . . . .
H14 H 1.0012 0.8365 1.1876 0.021 Uiso 1 1 calc R U . . .
C15 C 1.10970(15) 0.77071(14) 1.1713(2) 0.0202(5) Uani 1 1 d . . . . .
H15 H 1.1536 0.8031 1.2369 0.024 Uiso 1 1 calc R U . . .
C16 C 1.13724(15) 0.70502(14) 1.1072(2) 0.0204(5) Uani 1 1 d . . . . .
H16 H 1.1993 0.6937 1.1287 0.024 Uiso 1 1 calc R U . . .
C17 C 1.07485(14) 0.65503(14) 1.0108(2) 0.0179(5) Uani 1 1 d . . . . .
H17 H 1.0935 0.6095 0.9672 0.022 Uiso 1 1 calc R U . . .
C18 C 0.98466(14) 0.67400(13) 0.9808(2) 0.0151(4) Uani 1 1 d . . . . .
C19 C 0.90237(14) 0.63751(13) 0.8925(2) 0.0159(4) Uani 1 1 d . . . . .
C20 C 0.90744(15) 0.46836(13) 0.6894(2) 0.0172(5) Uani 1 1 d . . . . .
C21 C 1.08899(15) 0.42649(15) 0.7686(2) 0.0236(5) Uani 1 1 d . . . . .
H21A H 1.0829 0.4404 0.8587 0.028 Uiso 1 1 calc R U . . .
H21B H 1.1292 0.3773 0.7817 0.028 Uiso 1 1 calc R U . . .
C22 C 1.13166(17) 0.50001(16) 0.7211(3) 0.0324(6) Uani 1 1 d . . . . .
H22A H 1.1436 0.4848 0.6367 0.049 Uiso 1 1 calc R U . . .
H22B H 1.1880 0.5146 0.7922 0.049 Uiso 1 1 calc R U . . .
H22C H 1.0911 0.5483 0.7037 0.049 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 N5 2.0573(18) . ?
Co1 N2 2.0635(19) . ?
Co1 O1 2.2414(16) . ?
Co1 O2 2.3037(15) . ?
Co1 S1 2.3591(7) . ?
Co1 S3 2.3707(7) . ?
S1 C9 1.724(2) . ?
S2 C9 1.737(2) . ?
S2 C10 1.819(2) . ?
S3 C20 1.717(2) . ?
S4 C20 1.739(2) . ?
S4 C21 1.816(2) . ?
O1 C1 1.246(3) . ?
O2 C12 1.244(3) . ?
N1 C1 1.347(3) . ?
N1 C2 1.418(3) . ?
N1 H1 0.9099 . ?
N2 C8 1.301(3) . ?
N2 N3 1.362(2) . ?
N3 C9 1.331(3) . ?
N4 C12 1.353(3) . ?
N4 C13 1.414(3) . ?
N4 H4A 0.9098 . ?
N5 C19 1.304(3) . ?
N5 N6 1.360(2) . ?
N6 C20 1.334(3) . ?
C1 C8 1.492(3) . ?
C2 C3 1.374(3) . ?
C2 C7 1.413(3) . ?
C3 C4 1.400(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.403(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.393(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.450(3) . ?
C10 C11 1.525(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C19 1.488(3) . ?
C13 C14 1.381(3) . ?
C13 C18 1.414(3) . ?
C14 C15 1.400(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.399(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.391(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.446(3) . ?
C21 C22 1.511(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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
N5 Co1 N2 163.01(7) . . ?
N5 Co1 O1 91.98(6) . . ?
N2 Co1 O1 78.85(6) . . ?
N5 Co1 O2 78.16(6) . . ?
N2 Co1 O2 86.02(6) . . ?
O1 Co1 O2 79.21(6) . . ?
N5 Co1 S1 105.52(5) . . ?
N2 Co1 S1 81.21(5) . . ?
O1 Co1 S1 158.95(4) . . ?
O2 Co1 S1 92.79(5) . . ?
N5 Co1 S3 80.66(5) . . ?
N2 Co1 S3 113.58(5) . . ?
O1 Co1 S3 91.69(5) . . ?
O2 Co1 S3 156.58(4) . . ?
S1 Co1 S3 102.46(3) . . ?
C9 S1 Co1 94.91(8) . . ?
C9 S2 C10 104.08(11) . . ?
C20 S3 Co1 94.96(8) . . ?
C20 S4 C21 103.89(11) . . ?
C1 O1 Co1 106.42(13) . . ?
C12 O2 Co1 105.20(13) . . ?
C1 N1 C2 110.60(17) . . ?
C1 N1 H1 124.2 . . ?
C2 N1 H1 125.2 . . ?
C8 N2 N3 119.49(18) . . ?
C8 N2 Co1 115.65(14) . . ?
N3 N2 Co1 124.48(14) . . ?
C9 N3 N2 110.82(17) . . ?
C12 N4 C13 110.41(17) . . ?
C12 N4 H4A 120.7 . . ?
C13 N4 H4A 128.7 . . ?
C19 N5 N6 118.69(18) . . ?
C19 N5 Co1 116.61(14) . . ?
N6 N5 Co1 124.69(14) . . ?
C20 N6 N5 110.97(18) . . ?
O1 C1 N1 128.5(2) . . ?
O1 C1 C8 124.4(2) . . ?
N1 C1 C8 107.11(18) . . ?
C3 C2 C7 122.6(2) . . ?
C3 C2 N1 128.0(2) . . ?
C7 C2 N1 109.41(18) . . ?
C2 C3 C4 116.7(2) . . ?
C2 C3 H3 121.6 . . ?
C4 C3 H3 121.6 . . ?
C5 C4 C3 122.1(2) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C4 C5 C6 120.9(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 117.9(2) . . ?
C7 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?
C6 C7 C2 119.8(2) . . ?
C6 C7 C8 134.2(2) . . ?
C2 C7 C8 106.01(18) . . ?
N2 C8 C7 138.6(2) . . ?
N2 C8 C1 114.39(19) . . ?
C7 C8 C1 106.85(18) . . ?
N3 C9 S1 128.37(17) . . ?
N3 C9 S2 118.07(16) . . ?
S1 C9 S2 113.55(13) . . ?
C11 C10 S2 107.44(17) . . ?
C11 C10 H10A 110.2 . . ?
S2 C10 H10A 110.2 . . ?
C11 C10 H10B 110.2 . . ?
S2 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O2 C12 N4 128.16(19) . . ?
O2 C12 C19 125.18(19) . . ?
N4 C12 C19 106.65(18) . . ?
C14 C13 N4 127.95(19) . . ?
C14 C13 C18 122.1(2) . . ?
N4 C13 C18 109.92(18) . . ?
C13 C14 C15 116.6(2) . . ?
C13 C14 H14 121.7 . . ?
C15 C14 H14 121.7 . . ?
C16 C15 C14 122.4(2) . . ?
C16 C15 H15 118.8 . . ?
C14 C15 H15 118.8 . . ?
C15 C16 C17 120.8(2) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 118.0(2) . . ?
C18 C17 H17 121.0 . . ?
C16 C17 H17 121.0 . . ?
C17 C18 C13 120.14(19) . . ?
C17 C18 C19 134.5(2) . . ?
C13 C18 C19 105.36(18) . . ?
N5 C19 C18 137.5(2) . . ?
N5 C19 C12 114.78(18) . . ?
C18 C19 C12 107.65(18) . . ?
N6 C20 S3 127.80(17) . . ?
N6 C20 S4 117.53(17) . . ?
S3 C20 S4 114.66(13) . . ?
C22 C21 S4 113.95(17) . . ?
C22 C21 H21A 108.8 . . ?
S4 C21 H21A 108.8 . . ?
C22 C21 H21B 108.8 . . ?
S4 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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
C8 N2 N3 C9 -170.29(19) . . . . ?
Co1 N2 N3 C9 2.3(2) . . . . ?
C19 N5 N6 C20 -174.22(19) . . . . ?
Co1 N5 N6 C20 6.3(2) . . . . ?
Co1 O1 C1 N1 173.46(19) . . . . ?
Co1 O1 C1 C8 -5.2(2) . . . . ?
C2 N1 C1 O1 -178.2(2) . . . . ?
C2 N1 C1 C8 0.6(2) . . . . ?
C1 N1 C2 C3 178.8(2) . . . . ?
C1 N1 C2 C7 -0.9(2) . . . . ?
C7 C2 C3 C4 -0.2(3) . . . . ?
N1 C2 C3 C4 -179.8(2) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C4 C5 C6 C7 0.0(3) . . . . ?
C5 C6 C7 C2 -0.8(3) . . . . ?
C5 C6 C7 C8 178.9(2) . . . . ?
C3 C2 C7 C6 1.0(3) . . . . ?
N1 C2 C7 C6 -179.34(19) . . . . ?
C3 C2 C7 C8 -178.9(2) . . . . ?
N1 C2 C7 C8 0.8(2) . . . . ?
N3 N2 C8 C7 0.8(4) . . . . ?
Co1 N2 C8 C7 -172.4(2) . . . . ?
N3 N2 C8 C1 176.31(17) . . . . ?
Co1 N2 C8 C1 3.1(2) . . . . ?
C6 C7 C8 N2 -4.6(5) . . . . ?
C2 C7 C8 N2 175.2(3) . . . . ?
C6 C7 C8 C1 179.7(2) . . . . ?
C2 C7 C8 C1 -0.5(2) . . . . ?
O1 C1 C8 N2 1.9(3) . . . . ?
N1 C1 C8 N2 -176.93(18) . . . . ?
O1 C1 C8 C7 178.8(2) . . . . ?
N1 C1 C8 C7 0.0(2) . . . . ?
N2 N3 C9 S1 2.1(3) . . . . ?
N2 N3 C9 S2 -178.77(14) . . . . ?
Co1 S1 C9 N3 -4.4(2) . . . . ?
Co1 S1 C9 S2 176.51(10) . . . . ?
C10 S2 C9 N3 -1.0(2) . . . . ?
C10 S2 C9 S1 178.20(12) . . . . ?
C9 S2 C10 C11 170.95(16) . . . . ?
Co1 O2 C12 N4 -177.83(19) . . . . ?
Co1 O2 C12 C19 2.5(3) . . . . ?
C13 N4 C12 O2 179.1(2) . . . . ?
C13 N4 C12 C19 -1.2(2) . . . . ?
C12 N4 C13 C14 -177.5(2) . . . . ?
C12 N4 C13 C18 1.3(2) . . . . ?
N4 C13 C14 C15 179.5(2) . . . . ?
C18 C13 C14 C15 0.8(3) . . . . ?
C13 C14 C15 C16 0.0(3) . . . . ?
C14 C15 C16 C17 -0.7(3) . . . . ?
C15 C16 C17 C18 0.6(3) . . . . ?
C16 C17 C18 C13 0.2(3) . . . . ?
C16 C17 C18 C19 -178.4(2) . . . . ?
C14 C13 C18 C17 -0.9(3) . . . . ?
N4 C13 C18 C17 -179.79(19) . . . . ?
C14 C13 C18 C19 178.1(2) . . . . ?
N4 C13 C18 C19 -0.8(2) . . . . ?
N6 N5 C19 C18 -3.0(4) . . . . ?
Co1 N5 C19 C18 176.6(2) . . . . ?
N6 N5 C19 C12 179.43(17) . . . . ?
Co1 N5 C19 C12 -1.0(2) . . . . ?
C17 C18 C19 N5 1.2(5) . . . . ?
C13 C18 C19 N5 -177.6(3) . . . . ?
C17 C18 C19 C12 178.9(2) . . . . ?
C13 C18 C19 C12 0.1(2) . . . . ?
O2 C12 C19 N5 -1.3(3) . . . . ?
N4 C12 C19 N5 178.94(19) . . . . ?
O2 C12 C19 C18 -179.6(2) . . . . ?
N4 C12 C19 C18 0.6(2) . . . . ?
N5 N6 C20 S3 2.7(3) . . . . ?
N5 N6 C20 S4 -177.71(14) . . . . ?
Co1 S3 C20 N6 -7.9(2) . . . . ?
Co1 S3 C20 S4 172.51(11) . . . . ?
C21 S4 C20 N6 1.2(2) . . . . ?
C21 S4 C20 S3 -179.19(12) . . . . ?
C20 S4 C21 C22 -81.79(19) . . . . ?

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 O2 0.91 2.01 2.882(2) 160 4_575
N4 H4A O1 0.91 1.94 2.829(2) 167 4_576
C3 H3 N3 0.95 2.63 3.563(3) 168 4_575
C10 H10B Cg5 0.99 2.85 3.571(3) 130 3_666

_refine_diff_density_max         0.912
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.099

