# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_Co-2PPA
_database_code_depnum_ccdc_archive 'CCDC 2257024'
loop_
_audit_author_name
_audit_author_address
'Xiaoqiang Liang'
;Xian Polytechnic University
China
;
_audit_update_record             
;
2023-04-18 deposited with the CCDC.	2023-07-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 Co N10 O2 S2,2(H2 O)'
_chemical_formula_sum            'C20 H24 Co N10 O4 S2'
_chemical_formula_weight         591.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.703(7)
_cell_length_b                   9.477(9)
_cell_length_c                   10.206(10)
_cell_angle_alpha                112.963(12)
_cell_angle_beta                 102.917(13)
_cell_angle_gamma                95.919(13)
_cell_volume                     653.4(11)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5503
_cell_measurement_theta_min      2.269
_cell_measurement_theta_max      28.28

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_F_000             305
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.864
_shelx_estimated_absorpt_T_min   0.819
_shelx_estimated_absorpt_T_max   0.846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_T_max  0.84
_exptl_absorpt_process_details   SADABS;Bruker,2008

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ' phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7731
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.263
_diffrn_reflns_theta_max         25.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2566
_reflns_number_gt                2392
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'SMART (Brucker, 2008)'
_computing_cell_refinement       'SMART '
_computing_data_reduction        'SANIT (Brucker, 2008) '
_computing_structure_solution    'SHELXTL(Brucker, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL(Brucker, 2008)'
_computing_publication_material  'SHELXTL(Brucker, 2008)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0629P)²+0.2897P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2566
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0977
_refine_ls_wR_factor_gt          0.0944
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_restrained_S_all      0.978
_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
C1 C 0.7014(3) 0.2157(2) 0.5198(2) 0.0338(4) Uani 1 1 d . . . . .
C2 C 0.9190(3) -0.2340(2) 0.1598(2) 0.0396(5) Uani 1 1 d . . . . .
H2 H 0.9665 -0.3008 0.1982 0.048 Uiso 1 1 calc R U . . .
C3 C 0.8360(2) 0.0018(2) 0.1962(2) 0.0299(4) Uani 1 1 d . . . . .
H3 H 0.8230 0.0988 0.2607 0.036 Uiso 1 1 calc R U . . .
C4 C 0.8650(3) -0.2845(3) 0.0071(3) 0.0478(6) Uani 1 1 d . . . . .
H4 H 0.8745 -0.3839 -0.0551 0.057 Uiso 1 1 calc R U . . .
C5 C 0.7966(3) -0.1857(3) -0.0524(2) 0.0420(5) Uani 1 1 d . . . . .
H5 H 0.7610 -0.2175 -0.1546 0.050 Uiso 1 1 calc R U . . .
C6 C 0.7820(2) -0.0371(2) 0.0441(2) 0.0291(4) Uani 1 1 d . . . . .
C7 C 0.7089(2) 0.0787(2) -0.0070(2) 0.0290(4) Uani 1 1 d . . . . .
C8 C 0.6390(3) 0.0453(2) -0.1564(2) 0.0370(4) Uani 1 1 d . . . . .
H8 H 0.6357 -0.0513 -0.2314 0.044 Uiso 1 1 calc R U . . .
C9 C 0.6381(3) 0.3232(2) 0.0584(2) 0.0388(5) Uani 1 1 d . . . . .
C10 C 0.5744(3) 0.1632(3) -0.1879(2) 0.0402(5) Uani 1 1 d . . . . .
H10 H 0.5304 0.1444 -0.2871 0.048 Uiso 1 1 calc R U . . .
Co1 Co 1.0000 0.0000 0.5000 0.02937(14) Uani 1 2 d S . P . .
N1 N 0.7876(2) 0.1213(2) 0.5154(2) 0.0412(4) Uani 1 1 d . . . . .
N2 N 0.9055(2) -0.09139(19) 0.25561(18) 0.0324(4) Uani 1 1 d . . . . .
N3 N 0.7116(2) 0.2192(2) 0.10125(18) 0.0372(4) Uani 1 1 d . . . . .
N4 N 0.5717(2) 0.3027(2) -0.08386(19) 0.0397(4) Uani 1 1 d . . . . .
N5 N 0.6338(3) 0.4613(2) 0.1675(2) 0.0634(7) Uani 1 1 d . . . . .
H5A H 0.6543 0.4703 0.2553 0.076 Uiso 1 1 d R U . . .
H5B H 0.5826 0.5205 0.1482 0.076 Uiso 1 1 d R U . . .
O1 O 1.1615(2) 0.20256(18) 0.51364(18) 0.0472(4) Uani 1 1 d . . . . .
H1A H 1.2680 0.2135 0.5169 0.057 Uiso 1 1 d R U . . .
H1B H 1.1272 0.2513 0.4671 0.057 Uiso 1 1 d R U . . .
O2 O 0.0316(3) 0.3738(2) 0.3676(2) 0.0775(6) Uani 1 1 d . . . . .
H2A H 0.1194 0.4597 0.3838 0.093 Uiso 1 1 d R U . . .
H2B H -0.0624 0.3362 0.2738 0.093 Uiso 1 1 d R U . . .
S1 S 0.57958(9) 0.34881(8) 0.52326(9) 0.0600(2) Uani 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
C1 N1 1.161(3) . ?
C1 S1 1.642(2) . ?
C2 N2 1.355(3) . ?
C2 C4 1.385(4) . ?
C2 H2 0.9300 . ?
C3 N2 1.343(3) . ?
C3 C6 1.397(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.402(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.495(3) . ?
C7 N3 1.353(3) . ?
C7 C8 1.392(3) . ?
C8 C10 1.386(3) . ?
C8 H8 0.9300 . ?
C9 N3 1.350(3) . ?
C9 N4 1.355(3) . ?
C9 N5 1.357(3) . ?
C10 N4 1.340(3) . ?
C10 H10 0.9300 . ?
Co1 N1 2.094(2) 2_756 ?
Co1 N1 2.094(2) . ?
Co1 O1 2.115(2) . ?
Co1 O1 2.115(2) 2_756 ?
Co1 N2 2.208(3) . ?
Co1 N2 2.208(3) 2_756 ?
N5 H5A 0.8420 . ?
N5 H5B 0.7792 . ?
O1 H1A 0.8072 . ?
O1 H1B 0.8051 . ?
O2 H2A 0.9375 . ?
O2 H2B 0.9692 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 S1 179.07(19) . . ?
N2 C2 C4 122.75(19) . . ?
N2 C2 H2 118.6 . . ?
C4 C2 H2 118.6 . . ?
N2 C3 C6 124.46(18) . . ?
N2 C3 H3 117.8 . . ?
C6 C3 H3 117.8 . . ?
C2 C4 C5 119.5(2) . . ?
C2 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 119.0(2) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C3 C6 C5 117.28(18) . . ?
C3 C6 C7 118.93(17) . . ?
C5 C6 C7 123.78(18) . . ?
N3 C7 C8 121.11(18) . . ?
N3 C7 C6 116.05(17) . . ?
C8 C7 C6 122.83(18) . . ?
C10 C8 C7 116.72(19) . . ?
C10 C8 H8 121.6 . . ?
C7 C8 H8 121.6 . . ?
N3 C9 N4 125.60(19) . . ?
N3 C9 N5 117.1(2) . . ?
N4 C9 N5 117.30(19) . . ?
N4 C10 C8 123.90(19) . . ?
N4 C10 H10 118.0 . . ?
C8 C10 H10 118.0 . . ?
N1 Co1 N1 180.0 2_756 . ?
N1 Co1 O1 92.53(10) 2_756 . ?
N1 Co1 O1 87.47(10) . . ?
N1 Co1 O1 87.47(10) 2_756 2_756 ?
N1 Co1 O1 92.53(10) . 2_756 ?
O1 Co1 O1 180.0 . 2_756 ?
N1 Co1 N2 90.36(7) 2_756 . ?
N1 Co1 N2 89.64(7) . . ?
O1 Co1 N2 90.36(7) . . ?
O1 Co1 N2 89.64(7) 2_756 . ?
N1 Co1 N2 89.64(7) 2_756 2_756 ?
N1 Co1 N2 90.36(7) . 2_756 ?
O1 Co1 N2 89.64(7) . 2_756 ?
O1 Co1 N2 90.36(7) 2_756 2_756 ?
N2 Co1 N2 180.0 . 2_756 ?
C1 N1 Co1 162.29(18) . . ?
C3 N2 C2 116.98(18) . . ?
C3 N2 Co1 118.47(13) . . ?
C2 N2 Co1 124.50(13) . . ?
C7 N3 C9 117.30(18) . . ?
C10 N4 C9 115.24(18) . . ?
C9 N5 H5A 119.1 . . ?
C9 N5 H5B 120.5 . . ?
H5A N5 H5B 117.3 . . ?
Co1 O1 H1A 125.2 . . ?
Co1 O1 H1B 124.1 . . ?
H1A O1 H1B 100.5 . . ?
H2A O2 H2B 112.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C2 C4 C5 1.1(4) . . . . ?
C2 C4 C5 C6 -0.7(4) . . . . ?
N2 C3 C6 C5 2.1(3) . . . . ?
N2 C3 C6 C7 -179.23(17) . . . . ?
C4 C5 C6 C3 -0.8(3) . . . . ?
C4 C5 C6 C7 -179.4(2) . . . . ?
C3 C6 C7 N3 4.1(3) . . . . ?
C5 C6 C7 N3 -177.29(19) . . . . ?
C3 C6 C7 C8 -174.90(18) . . . . ?
C5 C6 C7 C8 3.7(3) . . . . ?
N3 C7 C8 C10 0.5(3) . . . . ?
C6 C7 C8 C10 179.51(18) . . . . ?
C7 C8 C10 N4 -1.9(3) . . . . ?
C6 C3 N2 C2 -1.7(3) . . . . ?
C6 C3 N2 Co1 175.74(14) . . . . ?
C4 C2 N2 C3 0.1(3) . . . . ?
C4 C2 N2 Co1 -177.20(17) . . . . ?
C8 C7 N3 C9 2.3(3) . . . . ?
C6 C7 N3 C9 -176.77(18) . . . . ?
N4 C9 N3 C7 -4.3(3) . . . . ?
N5 C9 N3 C7 177.1(2) . . . . ?
C8 C10 N4 C9 0.2(3) . . . . ?
N3 C9 N4 C10 3.0(3) . . . . ?
N5 C9 N4 C10 -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
C3 H3 N1 0.93 2.60 3.128(4) 116.3 .
C3 H3 O2 0.93 2.59 3.267(4) 130.2 1_655
N5 H5B N4 0.78 2.36 3.139(3) 178.7 2_665
O1 H1A S1 0.81 2.58 3.337(3) 157.4 1_655
O1 H1B O2 0.81 1.92 2.722(3) 174.9 1_655
O2 H2A S1 0.94 2.52 3.424(3) 160.7 2_666
O2 H2B N3 0.97 2.02 2.961(3) 164.0 1_455

_refine_diff_density_max         0.550
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.068

_shelxl_version_number           2014-3

_exptl_crystal_preparation       'proton conduction'
####################################################################### 
# 
# 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_Co-4PPA
_database_code_depnum_ccdc_archive 'CCDC 2257025'
loop_
_audit_author_name
_audit_author_address
'Xiaoqiang Liang'
;Xian Polytechnic University
China
;
_audit_update_record             
;
2023-04-18 deposited with the CCDC.	2023-07-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H32 Co N18 S2'
_chemical_formula_sum            'C38 H32 Co N18 S2'
_chemical_formula_weight         863.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.8166(16)
_cell_length_b                   11.069(2)
_cell_length_c                   11.929(2)
_cell_angle_alpha                72.386(3)
_cell_angle_beta                 78.707(3)
_cell_angle_gamma                80.019(3)
_cell_volume                     957.5(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6011
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      28.25

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_F_000             445
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.615
_shelx_estimated_absorpt_T_min   0.867
_shelx_estimated_absorpt_T_max   0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_process_details   SADABS;Bruker,2008

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ' phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13527
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.260
_diffrn_reflns_theta_max         28.339
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4777
_reflns_number_gt                4190
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'SMART (Brucker, 2008)'
_computing_cell_refinement       'SMART '
_computing_data_reduction        'SANIT (Brucker, 2008) '
_computing_structure_solution    'SHELXTL(Brucker, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL(Brucker, 2008)'
_computing_publication_material  'SHELXTL(Brucker, 2008)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0743P)²+0.0895P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4777
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.1047
_refine_ls_wR_factor_gt          0.1016
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
C1 C 0.21626(17) 0.31341(13) 0.57150(12) 0.0305(3) Uani 1 1 d . . . . .
C2 C 0.63579(19) 0.21947(14) 0.48253(15) 0.0396(3) Uani 1 1 d . . . . .
H2 H 0.5227 0.2074 0.5227 0.047 Uiso 1 1 calc R U . . .
C3 C 0.84848(17) 0.35121(13) 0.39326(12) 0.0300(3) Uani 1 1 d . . . . .
H3 H 0.8862 0.4313 0.3735 0.036 Uiso 1 1 calc R U . . .
C4 C 0.7451(2) 0.11556(14) 0.45792(15) 0.0415(4) Uani 1 1 d . . . . .
H4 H 0.7073 0.0351 0.4834 0.050 Uiso 1 1 calc R U . . .
C5 C 0.91146(19) 0.13269(13) 0.39484(13) 0.0351(3) Uani 1 1 d . . . . .
H5 H 0.9861 0.0644 0.3755 0.042 Uiso 1 1 calc R U . . .
C6 C 0.96559(17) 0.25332(13) 0.36078(11) 0.0286(3) Uani 1 1 d . . . . .
C7 C 1.14417(17) 0.27637(13) 0.29344(12) 0.0296(3) Uani 1 1 d . . . . .
C8 C 1.18294(19) 0.39810(14) 0.22731(14) 0.0359(3) Uani 1 1 d . . . . .
H8 H 1.0981 0.4690 0.2216 0.043 Uiso 1 1 calc R U . . .
C9 C 1.35359(19) 0.40849(14) 0.17056(14) 0.0385(3) Uani 1 1 d . . . . .
H9 H 1.3835 0.4891 0.1271 0.046 Uiso 1 1 calc R U . . .
C10 C 1.42557(18) 0.19486(15) 0.23652(13) 0.0359(3) Uani 1 1 d . . . . .
C11 C 0.38827(17) 0.36513(13) 0.77123(12) 0.0300(3) Uani 1 1 d . . . . .
H11 H 0.2763 0.4011 0.7544 0.036 Uiso 1 1 calc R U . . .
C12 C 0.68791(18) 0.34831(14) 0.71363(13) 0.0335(3) Uani 1 1 d . . . . .
H12 H 0.7850 0.3699 0.6560 0.040 Uiso 1 1 calc R U . . .
C13 C 0.71589(19) 0.26736(14) 0.82373(13) 0.0373(3) Uani 1 1 d . . . . .
H13 H 0.8295 0.2369 0.8401 0.045 Uiso 1 1 calc R U . . .
C14 C 0.57228(19) 0.23226(14) 0.90943(13) 0.0361(3) Uani 1 1 d . . . . .
H14 H 0.5882 0.1768 0.9837 0.043 Uiso 1 1 calc R U . . .
C15 C 0.40367(18) 0.28100(12) 0.88309(12) 0.0302(3) Uani 1 1 d . . . . .
C16 C 0.24207(18) 0.24128(13) 0.96596(12) 0.0306(3) Uani 1 1 d . . . . .
C17 C 0.2276(2) 0.11303(15) 1.02224(16) 0.0475(4) Uani 1 1 d . . . . .
H17 H 0.3219 0.0499 1.0168 0.057 Uiso 1 1 calc R U . . .
C18 C 0.0647(2) 0.08429(14) 1.08703(16) 0.0460(4) Uani 1 1 d . . . . .
H18 H 0.0502 -0.0012 1.1227 0.055 Uiso 1 1 calc R U . . .
C19 C -0.04038(18) 0.29391(13) 1.04968(12) 0.0310(3) Uani 1 1 d . . . . .
Co1 Co 0.5000 0.5000 0.5000 0.02636(9) Uani 1 2 d S . P . .
N1 N 0.28208(16) 0.40521(12) 0.51836(11) 0.0350(3) Uani 1 1 d . . . . .
N2 N 0.68455(15) 0.33763(11) 0.45132(10) 0.0313(2) Uani 1 1 d . . . . .
N3 N 1.26392(16) 0.17381(11) 0.29765(11) 0.0355(3) Uani 1 1 d . . . . .
N4 N 1.47696(16) 0.30930(13) 0.17489(12) 0.0390(3) Uani 1 1 d . . . . .
N5 N 1.54711(18) 0.09208(14) 0.23300(14) 0.0509(4) Uani 1 1 d . . . . .
H5A H 1.5221 0.0180 0.2722 0.061 Uiso 1 1 d R U . . .
H5B H 1.6548 0.1056 0.2069 0.061 Uiso 1 1 d R U . . .
N6 N 0.52628(15) 0.39733(11) 0.68605(10) 0.0301(2) Uani 1 1 d . . . . .
N7 N 0.11017(15) 0.33227(11) 0.97923(10) 0.0305(2) Uani 1 1 d . . . . .
N8 N -0.07085(17) 0.17069(12) 1.10121(12) 0.0376(3) Uani 1 1 d . . . . .
N9 N -0.17011(17) 0.38383(13) 1.07032(13) 0.0443(3) Uani 1 1 d . . . . .
H9A H -0.2663 0.3640 1.1063 0.053 Uiso 1 1 d R U . . .
H9B H -0.1519 0.4581 1.0446 0.053 Uiso 1 1 d R U . . .
S1 S 0.13307(6) 0.18289(4) 0.64836(4) 0.05108(13) Uani 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
C1 N1 1.1674(18) . ?
C1 S1 1.6251(14) . ?
C2 N2 1.3480(18) . ?
C2 C4 1.380(2) . ?
C2 H2 0.9300 . ?
C3 N2 1.3418(17) . ?
C3 C6 1.3906(18) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.3882(19) . ?
C5 H5 0.9300 . ?
C6 C7 1.4896(18) . ?
C7 N3 1.3353(17) . ?
C7 C8 1.3908(19) . ?
C8 C9 1.3795(19) . ?
C8 H8 0.9300 . ?
C9 N4 1.325(2) . ?
C9 H9 0.9300 . ?
C10 N4 1.343(2) . ?
C10 N3 1.3494(18) . ?
C10 N5 1.3554(19) . ?
C11 N6 1.3447(16) . ?
C11 C15 1.3908(19) . ?
C11 H11 0.9300 . ?
C12 N6 1.3476(18) . ?
C12 C13 1.381(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.385(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.393(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.4854(18) . ?
C16 N7 1.3324(17) . ?
C16 C17 1.388(2) . ?
C17 C18 1.388(2) . ?
C17 H17 0.9300 . ?
C18 N8 1.320(2) . ?
C18 H18 0.9300 . ?
C19 N9 1.3342(19) . ?
C19 N7 1.3570(17) . ?
C19 N8 1.3575(18) . ?
Co1 N1 2.0940(13) 2_666 ?
Co1 N1 2.0940(13) . ?
Co1 N6 2.1978(12) 2_666 ?
Co1 N6 2.1978(12) . ?
Co1 N2 2.2479(11) . ?
Co1 N2 2.2479(11) 2_666 ?
N5 H5A 0.8468 . ?
N5 H5B 0.8604 . ?
N9 H9A 0.8191 . ?
N9 H9B 0.8134 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 S1 177.26(13) . . ?
N2 C2 C4 123.34(13) . . ?
N2 C2 H2 118.3 . . ?
C4 C2 H2 118.3 . . ?
N2 C3 C6 124.24(12) . . ?
N2 C3 H3 117.9 . . ?
C6 C3 H3 117.9 . . ?
C2 C4 C5 119.09(13) . . ?
C2 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C4 C5 C6 119.03(13) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C3 117.72(12) . . ?
C5 C6 C7 121.03(12) . . ?
C3 C6 C7 121.25(12) . . ?
N3 C7 C8 121.73(12) . . ?
N3 C7 C6 116.57(12) . . ?
C8 C7 C6 121.68(12) . . ?
C9 C8 C7 116.67(13) . . ?
C9 C8 H8 121.7 . . ?
C7 C8 H8 121.7 . . ?
N4 C9 C8 123.27(14) . . ?
N4 C9 H9 118.4 . . ?
C8 C9 H9 118.4 . . ?
N4 C10 N3 125.86(13) . . ?
N4 C10 N5 116.16(13) . . ?
N3 C10 N5 117.95(14) . . ?
N6 C11 C15 123.65(13) . . ?
N6 C11 H11 118.2 . . ?
C15 C11 H11 118.2 . . ?
N6 C12 C13 122.93(13) . . ?
N6 C12 H12 118.5 . . ?
C13 C12 H12 118.5 . . ?
C12 C13 C14 119.03(13) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C13 C14 C15 119.22(13) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C11 C15 C14 117.74(12) . . ?
C11 C15 C16 119.21(12) . . ?
C14 C15 C16 122.95(12) . . ?
N7 C16 C17 121.83(12) . . ?
N7 C16 C15 117.56(11) . . ?
C17 C16 C15 120.54(12) . . ?
C18 C17 C16 116.26(14) . . ?
C18 C17 H17 121.9 . . ?
C16 C17 H17 121.9 . . ?
N8 C18 C17 124.14(13) . . ?
N8 C18 H18 117.9 . . ?
C17 C18 H18 117.9 . . ?
N9 C19 N7 117.90(12) . . ?
N9 C19 N8 116.78(13) . . ?
N7 C19 N8 125.32(13) . . ?
N1 Co1 N1 180.0 2_666 . ?
N1 Co1 N6 88.57(5) 2_666 2_666 ?
N1 Co1 N6 91.43(5) . 2_666 ?
N1 Co1 N6 91.43(5) 2_666 . ?
N1 Co1 N6 88.57(5) . . ?
N6 Co1 N6 180.0 2_666 . ?
N1 Co1 N2 88.67(5) 2_666 . ?
N1 Co1 N2 91.33(5) . . ?
N6 Co1 N2 93.46(4) 2_666 . ?
N6 Co1 N2 86.54(4) . . ?
N1 Co1 N2 91.33(5) 2_666 2_666 ?
N1 Co1 N2 88.67(5) . 2_666 ?
N6 Co1 N2 86.54(4) 2_666 2_666 ?
N6 Co1 N2 93.46(4) . 2_666 ?
N2 Co1 N2 180.0 . 2_666 ?
C1 N1 Co1 143.81(11) . . ?
C3 N2 C2 116.50(12) . . ?
C3 N2 Co1 122.66(9) . . ?
C2 N2 Co1 120.82(9) . . ?
C7 N3 C10 116.49(12) . . ?
C9 N4 C10 115.88(13) . . ?
C10 N5 H5A 119.7 . . ?
C10 N5 H5B 117.7 . . ?
H5A N5 H5B 120.5 . . ?
C11 N6 C12 117.34(12) . . ?
C11 N6 Co1 123.28(9) . . ?
C12 N6 Co1 118.72(9) . . ?
C16 N7 C19 116.93(11) . . ?
C18 N8 C19 115.25(13) . . ?
C19 N9 H9A 120.2 . . ?
C19 N9 H9B 118.3 . . ?
H9A N9 H9B 121.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C2 C4 C5 -2.1(3) . . . . ?
C2 C4 C5 C6 1.7(2) . . . . ?
C4 C5 C6 C3 0.5(2) . . . . ?
C4 C5 C6 C7 179.55(14) . . . . ?
N2 C3 C6 C5 -2.6(2) . . . . ?
N2 C3 C6 C7 178.33(13) . . . . ?
C5 C6 C7 N3 -18.8(2) . . . . ?
C3 C6 C7 N3 160.15(13) . . . . ?
C5 C6 C7 C8 159.67(14) . . . . ?
C3 C6 C7 C8 -21.3(2) . . . . ?
N3 C7 C8 C9 -2.9(2) . . . . ?
C6 C7 C8 C9 178.70(14) . . . . ?
C7 C8 C9 N4 1.3(2) . . . . ?
N6 C12 C13 C14 1.4(2) . . . . ?
C12 C13 C14 C15 -1.0(2) . . . . ?
N6 C11 C15 C14 3.0(2) . . . . ?
N6 C11 C15 C16 -173.51(12) . . . . ?
C13 C14 C15 C11 -1.0(2) . . . . ?
C13 C14 C15 C16 175.30(14) . . . . ?
C11 C15 C16 N7 -46.59(19) . . . . ?
C14 C15 C16 N7 137.13(15) . . . . ?
C11 C15 C16 C17 130.25(16) . . . . ?
C14 C15 C16 C17 -46.0(2) . . . . ?
N7 C16 C17 C18 3.9(3) . . . . ?
C15 C16 C17 C18 -172.82(16) . . . . ?
C16 C17 C18 N8 -2.7(3) . . . . ?
C6 C3 N2 C2 2.3(2) . . . . ?
C6 C3 N2 Co1 -179.40(10) . . . . ?
C4 C2 N2 C3 0.2(2) . . . . ?
C4 C2 N2 Co1 -178.18(13) . . . . ?
C8 C7 N3 C10 1.4(2) . . . . ?
C6 C7 N3 C10 179.95(12) . . . . ?
N4 C10 N3 C7 1.7(2) . . . . ?
N5 C10 N3 C7 -176.07(14) . . . . ?
C8 C9 N4 C10 1.5(2) . . . . ?
N3 C10 N4 C9 -3.2(2) . . . . ?
N5 C10 N4 C9 174.66(15) . . . . ?
C15 C11 N6 C12 -2.6(2) . . . . ?
C15 C11 N6 Co1 167.89(11) . . . . ?
C13 C12 N6 C11 0.4(2) . . . . ?
C13 C12 N6 Co1 -170.59(12) . . . . ?
C17 C16 N7 C19 -0.6(2) . . . . ?
C15 C16 N7 C19 176.21(12) . . . . ?
N9 C19 N7 C16 175.80(14) . . . . ?
N8 C19 N7 C16 -4.4(2) . . . . ?
C17 C18 N8 C19 -1.6(3) . . . . ?
N9 C19 N8 C18 -174.76(15) . . . . ?
N7 C19 N8 C18 5.4(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
N9 H9B N7 0.81 2.32 3.1180(19) 165.8 2_567
N9 H9A N4 0.82 2.13 2.9437(18) 171.2 1_356
N5 H5B N8 0.86 2.37 3.222(2) 168.7 1_754
C3 H3 N1 0.93 2.57 3.1253(19) 118.9 2_666
C2 H2 N1 0.93 2.62 3.1863(19) 119.6 .
N9 H9A N4 0.82 2.13 2.9437(18) 171.2 1_356
N9 H9B N7 0.81 2.32 3.1180(19) 165.8 2_567
N5 H5B N8 0.86 2.37 3.222(2) 168.7 1_754
C2 H2 N1 0.93 2.62 3.1863(19) 119.6 .
C3 H3 N1 0.93 2.57 3.1253(19) 118.9 2_666

_refine_diff_density_max         0.398
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.064

_shelxl_version_number           2014-3

