# Electronic Supplementary Material (ESI) for MedChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_H8QATSC
_database_code_depnum_ccdc_archive 'CCDC 1401684'
_audit_update_record             
;
2015-05-19 deposited with the CCDC.
2016-10-19 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         'C11 H10 N4 S'
_chemical_formula_sum            'C11 H10 N4 S'
_chemical_formula_weight         230.29

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

_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                   8.9464(9)
_cell_length_b                   12.8728(11)
_cell_length_c                   9.7816(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.947(8)
_cell_angle_gamma                90
_cell_volume                     1120.43(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5722
_cell_measurement_theta_min      3.1586
_cell_measurement_theta_max      29.0620

_exptl_crystal_description       tablets
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.265
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_T_min  0.69728
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.710689
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector_area_resol_mean 16.0696
_diffrn_measurement_method       'ω and φ'
_diffrn_reflns_number            16892
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.165
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2551
_reflns_number_gt                2116
_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       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis RED '
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'WinGX (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_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)+(0.0530P)²+0.2831P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2551
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1100
_refine_ls_wR_factor_gt          0.1026
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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 -0.18353(5) 0.11397(3) -0.05370(4) 0.05252(17) Uani 1 1 d . . . . .
N1 N 0.34588(14) -0.09621(10) 0.50513(14) 0.0448(3) Uani 1 1 d . . . . .
N2 N 0.03539(14) 0.10417(9) 0.31259(13) 0.0381(3) Uani 1 1 d . . . . .
N3 N -0.01663(15) 0.08137(11) 0.17884(13) 0.0426(3) Uani 1 1 d . . . . .
H3A H 0.024(2) 0.0263(17) 0.139(2) 0.062(6) Uiso 1 1 d . . . . .
N4 N -0.16830(15) 0.22464(11) 0.17567(14) 0.0440(3) Uani 1 1 d . . . . .
H4A H -0.135(2) 0.2354(15) 0.263(2) 0.060(5) Uiso 1 1 d . . . . .
H4B H -0.224(2) 0.2672(15) 0.1311(18) 0.049(5) Uiso 1 1 d . . . . .
C10 C 0.30179(15) -0.01258(11) 0.57735(15) 0.0360(3) Uani 1 1 d . . . . .
C5 C 0.36295(17) 0.00766(12) 0.71424(16) 0.0434(4) Uani 1 1 d . . . . .
C4 C 0.4769(2) -0.05906(15) 0.77288(19) 0.0565(5) Uani 1 1 d . . . . .
H4 H 0.5232 -0.0469 0.8656 0.068 Uiso 1 1 calc R U . . .
C3 C 0.5215(2) -0.14035(16) 0.6991(2) 0.0608(5) Uani 1 1 d . . . . .
H3 H 0.6006 -0.1865 0.7376 0.073 Uiso 1 1 calc R U . . .
C2 C 0.4511(2) -0.15634(14) 0.5662(2) 0.0550(4) Uani 1 1 d . . . . .
H2 H 0.4821 -0.2161 0.5157 0.066 Uiso 1 1 calc R U . . .
C11 C 0.13055(16) 0.03997(11) 0.37128(15) 0.0383(3) Uani 1 1 d . . . . .
H11 H 0.1622 -0.0198 0.3212 0.046 Uiso 1 1 calc R U . . .
C12 C -0.11986(16) 0.14341(12) 0.11039(15) 0.0375(3) Uani 1 1 d . . . . .
C9 C 0.19131(15) 0.05678(11) 0.51363(15) 0.0361(3) Uani 1 1 d . . . . .
C8 C 0.14285(18) 0.13864(13) 0.58837(17) 0.0447(4) Uani 1 1 d . . . . .
H8 H 0.0681 0.1860 0.5448 0.054 Uiso 1 1 calc R U . . .
C7 C 0.1989(2) 0.15526(14) 0.72584(18) 0.0531(4) Uani 1 1 d . . . . .
H7 H 0.1601 0.2118 0.7774 0.064 Uiso 1 1 calc R U . . .
C6 C 0.3078(2) 0.09180(14) 0.78658(18) 0.0538(4) Uani 1 1 d . . . . .
H6 H 0.3482 0.1046 0.8810 0.065 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
S1 C12 1.6897(15) . ?
N1 C2 1.314(2) . ?
N1 C10 1.368(2) . ?
N2 C11 1.2791(18) . ?
N2 N3 1.3741(18) . ?
N3 C12 1.3457(19) . ?
N3 H3A 0.90(2) . ?
N4 C12 1.321(2) . ?
N4 H4A 0.884(19) . ?
N4 H4B 0.834(19) . ?
C10 C5 1.417(2) . ?
C10 C9 1.427(2) . ?
C5 C4 1.409(2) . ?
C5 C6 1.410(2) . ?
C4 C3 1.354(3) . ?
C4 H4 0.9700 . ?
C3 C2 1.399(3) . ?
C3 H3 0.9700 . ?
C2 H2 0.9700 . ?
C11 C9 1.457(2) . ?
C11 H11 0.9700 . ?
C9 C8 1.378(2) . ?
C8 C7 1.402(2) . ?
C8 H8 0.9700 . ?
C7 C6 1.360(3) . ?
C7 H7 0.9700 . ?
C6 H6 0.9700 . ?

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
C2 N1 C10 117.39(14) . . ?
C11 N2 N3 115.68(13) . . ?
C12 N3 N2 119.62(13) . . ?
C12 N3 H3A 122.7(12) . . ?
N2 N3 H3A 117.6(12) . . ?
C12 N4 H4A 119.8(13) . . ?
C12 N4 H4B 118.5(12) . . ?
H4A N4 H4B 121.5(17) . . ?
N1 C10 C5 121.93(14) . . ?
N1 C10 C9 119.39(13) . . ?
C5 C10 C9 118.68(14) . . ?
C4 C5 C6 122.67(15) . . ?
C4 C5 C10 117.70(15) . . ?
C6 C5 C10 119.63(14) . . ?
C3 C4 C5 119.64(17) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C3 C2 118.65(16) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
N1 C2 C3 124.63(17) . . ?
N1 C2 H2 117.7 . . ?
C3 C2 H2 117.7 . . ?
N2 C11 C9 119.86(13) . . ?
N2 C11 H11 120.1 . . ?
C9 C11 H11 120.1 . . ?
N4 C12 N3 118.14(14) . . ?
N4 C12 S1 122.78(12) . . ?
N3 C12 S1 119.07(12) . . ?
C8 C9 C10 119.26(14) . . ?
C8 C9 C11 120.91(13) . . ?
C10 C9 C11 119.83(13) . . ?
C9 C8 C7 121.64(15) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C6 C7 C8 119.75(16) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C7 C6 C5 120.93(15) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?

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
C11 N2 N3 C12 178.36(13) . . . . ?
C2 N1 C10 C5 -1.8(2) . . . . ?
C2 N1 C10 C9 178.03(14) . . . . ?
N1 C10 C5 C4 2.8(2) . . . . ?
C9 C10 C5 C4 -177.10(13) . . . . ?
N1 C10 C5 C6 -176.64(14) . . . . ?
C9 C10 C5 C6 3.5(2) . . . . ?
C6 C5 C4 C3 177.98(18) . . . . ?
C10 C5 C4 C3 -1.4(3) . . . . ?
C5 C4 C3 C2 -0.7(3) . . . . ?
C10 N1 C2 C3 -0.5(3) . . . . ?
C4 C3 C2 N1 1.8(3) . . . . ?
N3 N2 C11 C9 -179.40(12) . . . . ?
N2 N3 C12 N4 -0.3(2) . . . . ?
N2 N3 C12 S1 -179.63(10) . . . . ?
N1 C10 C9 C8 177.50(14) . . . . ?
C5 C10 C9 C8 -2.6(2) . . . . ?
N1 C10 C9 C11 -2.1(2) . . . . ?
C5 C10 C9 C11 177.76(13) . . . . ?
N2 C11 C9 C8 2.8(2) . . . . ?
N2 C11 C9 C10 -177.56(13) . . . . ?
C10 C9 C8 C7 -0.3(2) . . . . ?
C11 C9 C8 C7 179.28(14) . . . . ?
C9 C8 C7 C6 2.5(3) . . . . ?
C8 C7 C6 C5 -1.6(3) . . . . ?
C4 C5 C6 C7 179.21(17) . . . . ?
C10 C5 C6 C7 -1.4(3) . . . . ?

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
N3 H3A S1 0.90(2) 2.50(2) 3.3885(15) 168.8(17) 3
N4 H4A S1 0.884(19) 2.71(2) 3.3789(14) 133.8(16) 4_566
N4 H4B N1 0.834(19) 2.398(19) 3.223(2) 170.1(16) 2

_refine_diff_density_max         0.208
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.049


####################################################################### 
# 
# 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_nfjv3s
_database_code_depnum_ccdc_archive 'CCDC 1401685'
_audit_update_record             
;
2015-05-19 deposited with the CCDC.
2016-10-19 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 N8 O2, 2 (Cl), 2 (H2 O)'
_chemical_formula_sum            'C22 H24 Cl2 Co N8 O4'
_chemical_formula_weight         594.32

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.752(3)
_cell_length_b                   10.0815(9)
_cell_length_c                   13.905(2)
_cell_angle_alpha                90
_cell_angle_beta                 124.39(2)
_cell_angle_gamma                90
_cell_volume                     2516.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5895
_cell_measurement_theta_min      2.9359
_cell_measurement_theta_max      29.1122

_exptl_crystal_description       tablets
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_F_000             1220
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.941
_shelx_estimated_absorpt_T_min   0.872
_shelx_estimated_absorpt_T_max   0.920
_exptl_absorpt_correction_T_min  0.58536
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.710689
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector_area_resol_mean 16.0696
_diffrn_measurement_method       'ω and φ'
_diffrn_reflns_number            18343
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.942
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2881
_reflns_number_gt                2365
_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       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis RED '
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'WinGX (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_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)+(0.0443P)²+2.4030P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2881
_refine_ls_number_parameters     188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1034
_refine_ls_wR_factor_gt          0.0951
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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 0.0000 0.10972(4) 0.7500 0.03239(14) Uani 1 2 d S T P . .
O1 O 0.07721(9) -0.03422(16) 0.86082(14) 0.0421(4) Uani 1 1 d . . . . .
N1 N 0.06231(10) 0.25712(19) 0.87941(16) 0.0368(4) Uani 1 1 d . . . . .
N2 N 0.06009(10) 0.07925(18) 0.67859(17) 0.0341(4) Uani 1 1 d . . . . .
N3 N 0.11252(11) -0.0184(2) 0.73613(18) 0.0424(5) Uani 1 1 d . . . . .
HN3 H 0.1393(15) -0.040(3) 0.714(2) 0.047(7) Uiso 1 1 d . . . . .
N4 N 0.16902(13) -0.1665(3) 0.8880(2) 0.0527(6) Uani 1 1 d . . . . .
H4A H 0.1764(15) -0.191(3) 0.951(3) 0.052(9) Uiso 1 1 d . . . . .
H4B H 0.1951(15) -0.191(3) 0.867(2) 0.051(8) Uiso 1 1 d . . . . .
C2 C 0.11494(14) 0.3140(3) 0.8732(2) 0.0495(6) Uani 1 1 d . . . . .
H2 H 0.1201 0.2853 0.8115 0.059 Uiso 1 1 calc R U . . .
C3 C 0.16337(17) 0.4120(3) 0.9488(3) 0.0580(8) Uani 1 1 d . . . . .
H3 H 0.2012 0.4492 0.9403 0.070 Uiso 1 1 calc R U . . .
C4 C 0.15615(15) 0.4540(3) 1.0345(2) 0.0501(6) Uani 1 1 d . . . . .
H4 H 0.1882 0.5236 1.0874 0.060 Uiso 1 1 calc R U . . .
C5 C 0.10174(13) 0.3959(2) 1.0463(2) 0.0398(5) Uani 1 1 d . . . . .
C6 C 0.09494(15) 0.4370(3) 1.1370(2) 0.0491(6) Uani 1 1 d . . . . .
H6 H 0.1269 0.5068 1.1898 0.059 Uiso 1 1 calc R U . . .
C7 C 0.04409(16) 0.3794(3) 1.1505(2) 0.0539(7) Uani 1 1 d . . . . .
H7 H 0.0394 0.4076 1.2127 0.065 Uiso 1 1 calc R U . . .
C8 C -0.00161(14) 0.2787(3) 1.0738(2) 0.0461(6) Uani 1 1 d . . . . .
H8 H -0.0375 0.2380 1.0851 0.055 Uiso 1 1 calc R U . . .
C9 C 0.00160(12) 0.2345(2) 0.98325(19) 0.0346(5) Uani 1 1 d . . . . .
C10 C 0.05541(11) 0.2954(2) 0.96734(18) 0.0333(5) Uani 1 1 d . . . . .
C11 C 0.05047(13) 0.1290(2) 0.5861(2) 0.0370(5) Uani 1 1 d . . . . .
H11 H 0.0803 0.0932 0.5604 0.044 Uiso 1 1 calc R U . . .
C12 C 0.11849(12) -0.0722(2) 0.8307(2) 0.0381(5) Uani 1 1 d . . . . .
Cl1 Cl 0.21986(4) 0.10374(7) 1.16340(6) 0.0523(2) Uani 1 1 d . . . . .
O1W O 0.21574(14) -0.2034(3) 1.1297(2) 0.0658(6) Uani 1 1 d . . . . .
H1W H 0.223(2) -0.131(4) 1.147(3) 0.074(13) Uiso 1 1 d . . . . .
H2W H 0.2209(16) -0.243(3) 1.182(3) 0.052(10) 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
Co1 N2 2.0628(18) . ?
Co1 N2 2.0629(18) 2_556 ?
Co1 O1 2.0922(16) . ?
Co1 O1 2.0922(17) 2_556 ?
Co1 N1 2.1279(19) . ?
Co1 N1 2.1279(19) 2_556 ?
O1 C12 1.246(3) . ?
N1 C2 1.326(3) . ?
N1 C10 1.369(3) . ?
N2 C11 1.283(3) . ?
N2 N3 1.371(3) . ?
N3 C12 1.360(3) . ?
N3 HN3 0.83(3) . ?
N4 C12 1.325(3) . ?
N4 H4A 0.83(3) . ?
N4 H4B 0.81(3) . ?
C2 C3 1.392(4) . ?
C2 H2 0.9700 . ?
C3 C4 1.355(4) . ?
C3 H3 0.9700 . ?
C4 C5 1.411(3) . ?
C4 H4 0.9700 . ?
C5 C6 1.412(3) . ?
C5 C10 1.414(3) . ?
C6 C7 1.353(4) . ?
C6 H6 0.9700 . ?
C7 C8 1.399(4) . ?
C7 H7 0.9700 . ?
C8 C9 1.374(3) . ?
C8 H8 0.9700 . ?
C9 C10 1.445(3) . ?
C9 C11 1.453(3) 2_556 ?
C11 C9 1.453(3) 2_556 ?
C11 H11 0.9700 . ?
O1W H1W 0.76(4) . ?
O1W H2W 0.78(3) . ?

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 Co1 N2 162.87(11) . 2_556 ?
N2 Co1 O1 77.76(7) . . ?
N2 Co1 O1 90.32(7) 2_556 . ?
N2 Co1 O1 90.31(7) . 2_556 ?
N2 Co1 O1 77.76(7) 2_556 2_556 ?
O1 Co1 O1 92.17(10) . 2_556 ?
N2 Co1 N1 103.70(7) . . ?
N2 Co1 N1 88.34(7) 2_556 . ?
O1 Co1 N1 89.92(7) . . ?
O1 Co1 N1 165.95(6) 2_556 . ?
N2 Co1 N1 88.34(7) . 2_556 ?
N2 Co1 N1 103.70(7) 2_556 2_556 ?
O1 Co1 N1 165.95(6) . 2_556 ?
O1 Co1 N1 89.93(7) 2_556 2_556 ?
N1 Co1 N1 91.41(11) . 2_556 ?
C12 O1 Co1 113.39(15) . . ?
C2 N1 C10 118.0(2) . . ?
C2 N1 Co1 114.10(16) . . ?
C10 N1 Co1 127.83(14) . . ?
C11 N2 N3 118.47(19) . . ?
C11 N2 Co1 129.47(16) . . ?
N3 N2 Co1 111.74(14) . . ?
C12 N3 N2 116.42(19) . . ?
C12 N3 HN3 123.5(19) . . ?
N2 N3 HN3 120.0(19) . . ?
C12 N4 H4A 117(2) . . ?
C12 N4 H4B 121(2) . . ?
H4A N4 H4B 122(3) . . ?
N1 C2 C3 124.8(2) . . ?
N1 C2 H2 117.6 . . ?
C3 C2 H2 117.6 . . ?
C4 C3 C2 118.1(2) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
C3 C4 C5 119.7(2) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 120.0(2) . . ?
C4 C5 C10 118.9(2) . . ?
C6 C5 C10 121.0(2) . . ?
C7 C6 C5 120.3(2) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 119.3(2) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C9 C8 C7 123.5(2) . . ?
C9 C8 H8 118.3 . . ?
C7 C8 H8 118.3 . . ?
C8 C9 C10 117.9(2) . . ?
C8 C9 C11 114.9(2) . 2_556 ?
C10 C9 C11 127.2(2) . 2_556 ?
N1 C10 C5 120.4(2) . . ?
N1 C10 C9 121.6(2) . . ?
C5 C10 C9 118.0(2) . . ?
N2 C11 C9 125.2(2) . 2_556 ?
N2 C11 H11 117.4 . . ?
C9 C11 H11 117.4 2_556 . ?
O1 C12 N4 122.0(2) . . ?
O1 C12 N3 120.6(2) . . ?
N4 C12 N3 117.5(2) . . ?
H1W O1W H2W 107(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
C11 N2 N3 C12 -177.2(2) . . . . ?
Co1 N2 N3 C12 -3.1(3) . . . . ?
C10 N1 C2 C3 -1.1(4) . . . . ?
Co1 N1 C2 C3 -179.3(2) . . . . ?
N1 C2 C3 C4 -0.7(5) . . . . ?
C2 C3 C4 C5 1.5(5) . . . . ?
C3 C4 C5 C6 178.6(3) . . . . ?
C3 C4 C5 C10 -0.5(4) . . . . ?
C4 C5 C6 C7 -178.4(3) . . . . ?
C10 C5 C6 C7 0.7(4) . . . . ?
C5 C6 C7 C8 0.0(4) . . . . ?
C6 C7 C8 C9 -0.5(4) . . . . ?
C7 C8 C9 C10 0.3(4) . . . . ?
C7 C8 C9 C11 179.8(2) . . . 2_556 ?
C2 N1 C10 C5 2.1(3) . . . . ?
Co1 N1 C10 C5 -179.96(16) . . . . ?
C2 N1 C10 C9 -177.4(2) . . . . ?
Co1 N1 C10 C9 0.6(3) . . . . ?
C4 C5 C10 N1 -1.3(3) . . . . ?
C6 C5 C10 N1 179.6(2) . . . . ?
C4 C5 C10 C9 178.2(2) . . . . ?
C6 C5 C10 C9 -0.9(3) . . . . ?
C8 C9 C10 N1 179.9(2) . . . . ?
C11 C9 C10 N1 0.4(3) 2_556 . . . ?
C8 C9 C10 C5 0.4(3) . . . . ?
C11 C9 C10 C5 -179.1(2) 2_556 . . . ?
N3 N2 C11 C9 -178.7(2) . . . 2_556 ?
Co1 N2 C11 C9 8.4(3) . . . 2_556 ?
Co1 O1 C12 N4 -177.5(2) . . . . ?
Co1 O1 C12 N3 1.9(3) . . . . ?
N2 N3 C12 O1 0.9(3) . . . . ?
N2 N3 C12 N4 -179.7(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
N3 HN3 Cl1 0.83(3) 2.31(3) 3.144(2) 176(3) 6
N4 H4A O1W 0.83(3) 2.13(3) 2.934(4) 163(3) .
N4 H4B O1W 0.81(3) 2.19(3) 2.960(3) 159(3) 7_547
O1W H1W Cl1 0.76(4) 2.38(4) 3.125(3) 167(4) .
O1W H2W Cl1 0.78(3) 2.35(3) 3.077(3) 155(3) 4_547

_refine_diff_density_max         0.398
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.057


####################################################################### 
# 
# 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_nfjv2dry
_database_code_depnum_ccdc_archive 'CCDC 1401686'
_audit_update_record             
;
2015-05-19 deposited with the CCDC.
2016-10-19 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 H18 Co N8 S2, Cl O4, C2 O S'
_chemical_formula_sum            'C24 H18 Cl Co N8 O5 S3'
_chemical_formula_weight         689.02

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'
Cl Cl 0.1484 0.1585 '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      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                   10.3016(6)
_cell_length_b                   10.5421(7)
_cell_length_c                   14.5516(10)
_cell_angle_alpha                80.662(6)
_cell_angle_beta                 89.829(5)
_cell_angle_gamma                65.733(6)
_cell_volume                     1418.02(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6995
_cell_measurement_theta_min      2.8386
_cell_measurement_theta_max      29.0731

_exptl_crystal_description       tablets
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_F_000             700
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.972
_shelx_estimated_absorpt_T_min   0.918
_shelx_estimated_absorpt_T_max   0.926
_exptl_absorpt_correction_T_min  0.95527
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.710689
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector_area_resol_mean 16.0696
_diffrn_measurement_method       'ω and φ'
_diffrn_reflns_number            20909
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.844
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6165
_reflns_number_gt                4897
_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       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis RED '
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'WinGX (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0592P)²+1.1216P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6165
_refine_ls_number_parameters     389
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1263
_refine_ls_wR_factor_gt          0.1161
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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 0.88978(4) 0.15287(4) 0.68040(3) 0.02050(12) Uani 1 1 d . . . . .
S1 S 0.92496(8) 0.16337(7) 0.52992(5) 0.02569(17) Uani 1 1 d . . . . .
S2 S 1.11829(7) 0.01694(7) 0.71902(6) 0.02771(18) Uani 1 1 d . . . . .
N1 N 0.8481(2) 0.1451(3) 0.81730(17) 0.0265(5) Uani 1 1 d . . . . .
N2 N 0.9463(2) 0.3059(2) 0.67471(16) 0.0221(5) Uani 1 1 d . . . . .
N3 N 0.9725(2) 0.3701(2) 0.59005(17) 0.0250(5) Uani 1 1 d . . . . .
N4 N 0.9947(3) 0.3576(3) 0.43487(17) 0.0312(6) Uani 1 1 d . . . . .
H41 H 1.0166 0.4289 0.4272 0.037 Uiso 1 1 calc R U . . .
H42 H 0.9911 0.3183 0.3882 0.037 Uiso 1 1 calc R U . . .
C2 C 0.7821(3) 0.0658(4) 0.8531(2) 0.0352(7) Uani 1 1 d . . . . .
H2 H 0.7489 0.0212 0.8109 0.042 Uiso 1 1 calc R U . . .
C3 C 0.7571(4) 0.0420(4) 0.9468(3) 0.0446(9) Uani 1 1 d . . . . .
H3 H 0.7080 -0.0173 0.9686 0.054 Uiso 1 1 calc R U . . .
C4 C 0.8024(4) 0.1032(4) 1.0076(3) 0.0451(9) Uani 1 1 d . . . . .
H4 H 0.7873 0.0869 1.0735 0.054 Uiso 1 1 calc R U . . .
C5 C 0.8712(4) 0.1897(4) 0.9739(2) 0.0374(7) Uani 1 1 d . . . . .
C6 C 0.9254(4) 0.2513(4) 1.0353(3) 0.0511(10) Uani 1 1 d . . . . .
H6 H 0.9130 0.2345 1.1016 0.061 Uiso 1 1 calc R U . . .
C7 C 0.9935(5) 0.3323(4) 1.0031(3) 0.0553(10) Uani 1 1 d . . . . .
H7 H 1.0328 0.3709 1.0460 0.066 Uiso 1 1 calc R U . . .
C8 C 1.0074(4) 0.3606(4) 0.9072(3) 0.0446(9) Uani 1 1 d . . . . .
H8 H 1.0532 0.4226 0.8846 0.054 Uiso 1 1 calc R U . . .
C9 C 0.9581(3) 0.3032(3) 0.8429(2) 0.0307(7) Uani 1 1 d . . . . .
C10 C 0.8916(3) 0.2119(3) 0.8767(2) 0.0289(6) Uani 1 1 d . . . . .
C11 C 0.9769(3) 0.3487(3) 0.7466(2) 0.0296(6) Uani 1 1 d . . . . .
H11 H 1.0165 0.4184 0.7347 0.036 Uiso 1 1 calc R U . . .
C12 C 0.9663(3) 0.3079(3) 0.5194(2) 0.0223(6) Uani 1 1 d . . . . .
N1A N 0.6813(2) 0.2817(2) 0.64869(17) 0.0247(5) Uani 1 1 d . . . . .
N2A N 0.8698(2) -0.0181(2) 0.67350(16) 0.0231(5) Uani 1 1 d . . . . .
N3A N 0.9854(3) -0.1490(2) 0.69421(18) 0.0269(5) Uani 1 1 d . . . . .
N4A N 1.2231(3) -0.2605(3) 0.7386(2) 0.0372(6) Uani 1 1 d . . . . .
H4A1 H 1.2201 -0.3408 0.7384 0.045 Uiso 1 1 calc R U . . .
H4A2 H 1.3023 -0.2572 0.7533 0.045 Uiso 1 1 calc R U . . .
C2A C 0.6394(3) 0.4184(3) 0.6528(2) 0.0327(7) Uani 1 1 d . . . . .
H2A H 0.7094 0.4480 0.6751 0.039 Uiso 1 1 calc R U . . .
C3A C 0.5013(3) 0.5212(3) 0.6269(2) 0.0384(8) Uani 1 1 d . . . . .
H3A H 0.4772 0.6196 0.6297 0.046 Uiso 1 1 calc R U . . .
C4A C 0.4014(3) 0.4814(4) 0.5978(2) 0.0397(8) Uani 1 1 d . . . . .
H4A H 0.3052 0.5514 0.5782 0.048 Uiso 1 1 calc R U . . .
C5A C 0.4375(3) 0.3390(4) 0.5961(2) 0.0356(7) Uani 1 1 d . . . . .
C6A C 0.3327(4) 0.2929(4) 0.5714(3) 0.0485(9) Uani 1 1 d . . . . .
H6A H 0.2362 0.3620 0.5515 0.058 Uiso 1 1 calc R U . . .
C7A C 0.3662(4) 0.1530(4) 0.5754(3) 0.0528(10) Uani 1 1 d . . . . .
H7A H 0.2930 0.1223 0.5609 0.063 Uiso 1 1 calc R U . . .
C8A C 0.5066(4) 0.0538(4) 0.6004(3) 0.0439(8) Uani 1 1 d . . . . .
H8A H 0.5289 -0.0455 0.6029 0.053 Uiso 1 1 calc R U . . .
C9A C 0.6155(3) 0.0922(3) 0.6220(2) 0.0309(7) Uani 1 1 d . . . . .
C10A C 0.5809(3) 0.2381(3) 0.6218(2) 0.0275(6) Uani 1 1 d . . . . .
C11A C 0.7533(3) -0.0241(3) 0.6457(2) 0.0295(6) Uani 1 1 d . . . . .
H11A H 0.7597 -0.1170 0.6404 0.035 Uiso 1 1 calc R U . . .
C12A C 1.1042(3) -0.1404(3) 0.7161(2) 0.0258(6) Uani 1 1 d . . . . .
Cl1 Cl 1.61882(15) -0.27731(15) 0.80863(11) 0.0804(4) Uani 1 1 d . . . . .
O2 O 1.6563(8) -0.1805(8) 0.8381(4) 0.188(3) Uani 1 1 d . . . . .
O3 O 1.6627(9) -0.2962(7) 0.7175(4) 0.185(3) Uani 1 1 d . . . . .
O4 O 1.4805(6) -0.2320(8) 0.8077(7) 0.240(4) Uani 1 1 d . . . . .
O5 O 1.6770(10) -0.4037(7) 0.8630(5) 0.264(5) Uani 1 1 d . . . . .
S3 S 1.39123(13) -0.65502(12) 0.82439(9) 0.0533(5) Uani 0.856(4) 1 d . . P . .
S3A S 1.3020(13) -0.6266(12) 0.8809(10) 0.105(5) Uani 0.144(4) 1 d . . P . .
O1 O 1.2440(3) -0.5470(3) 0.7862(2) 0.0614(8) Uani 1 1 d . . . . .
C13 C 1.3729(6) -0.8111(6) 0.8684(7) 0.163(4) Uani 1 1 d . . . . .
C14 C 1.4335(9) -0.5976(9) 0.9234(6) 0.162(4) 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
Co1 N2A 1.914(2) . ?
Co1 N2 1.917(2) . ?
Co1 N1A 2.019(2) . ?
Co1 N1 2.032(2) . ?
Co1 S2 2.2101(8) . ?
Co1 S1 2.2108(8) . ?
S1 C12 1.728(3) . ?
S2 C12A 1.730(3) . ?
N1 C2 1.326(4) . ?
N1 C10 1.379(4) . ?
N2 C11 1.292(4) . ?
N2 N3 1.388(3) . ?
N3 C12 1.320(4) . ?
N4 C12 1.338(4) . ?
N4 H41 0.8600 . ?
N4 H42 0.8600 . ?
C2 C3 1.389(5) . ?
C2 H2 0.9700 . ?
C3 C4 1.361(5) . ?
C3 H3 0.9700 . ?
C4 C5 1.400(5) . ?
C4 H4 0.9700 . ?
C5 C6 1.421(5) . ?
C5 C10 1.426(4) . ?
C6 C7 1.342(6) . ?
C6 H6 0.9700 . ?
C7 C8 1.398(5) . ?
C7 H7 0.9700 . ?
C8 C9 1.393(4) . ?
C8 H8 0.9700 . ?
C9 C10 1.422(4) . ?
C9 C11 1.445(4) . ?
C11 H11 0.9700 . ?
N1A C2A 1.336(4) . ?
N1A C10A 1.373(4) . ?
N2A C11A 1.296(4) . ?
N2A N3A 1.390(3) . ?
N3A C12A 1.308(4) . ?
N4A C12A 1.343(4) . ?
N4A H4A1 0.8600 . ?
N4A H4A2 0.8600 . ?
C2A C3A 1.395(4) . ?
C2A H2A 0.9700 . ?
C3A C4A 1.353(5) . ?
C3A H3A 0.9700 . ?
C4A C5A 1.394(5) . ?
C4A H4A 0.9700 . ?
C5A C6A 1.422(5) . ?
C5A C10A 1.427(4) . ?
C6A C7A 1.361(5) . ?
C6A H6A 0.9700 . ?
C7A C8A 1.398(5) . ?
C7A H7A 0.9700 . ?
C8A C9A 1.392(4) . ?
C8A H8A 0.9700 . ?
C9A C10A 1.429(4) . ?
C9A C11A 1.439(4) . ?
C11A H11A 0.9700 . ?
Cl1 O4 1.303(5) . ?
Cl1 O5 1.328(6) . ?
Cl1 O2 1.357(5) . ?
Cl1 O3 1.418(6) . ?
S3 S3A 1.208(12) . ?
S3 O1 1.512(3) . ?
S3 C13 1.751(6) . ?
S3 C14 1.771(8) . ?
S3A O1 1.476(14) . ?
S3A C14 1.648(16) . ?
S3A C13 1.815(14) . ?

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
N2A Co1 N2 167.90(9) . . ?
N2A Co1 N1A 95.48(9) . . ?
N2 Co1 N1A 93.85(9) . . ?
N2A Co1 N1 93.27(10) . . ?
N2 Co1 N1 94.78(10) . . ?
N1A Co1 N1 87.80(10) . . ?
N2A Co1 S2 86.26(7) . . ?
N2 Co1 S2 84.62(7) . . ?
N1A Co1 S2 177.79(7) . . ?
N1 Co1 S2 90.74(7) . . ?
N2A Co1 S1 85.83(7) . . ?
N2 Co1 S1 86.50(7) . . ?
N1A Co1 S1 89.88(7) . . ?
N1 Co1 S1 177.42(7) . . ?
S2 Co1 S1 91.62(3) . . ?
C12 S1 Co1 95.35(10) . . ?
C12A S2 Co1 95.25(10) . . ?
C2 N1 C10 117.9(3) . . ?
C2 N1 Co1 118.5(2) . . ?
C10 N1 Co1 123.55(19) . . ?
C11 N2 N3 114.2(2) . . ?
C11 N2 Co1 124.8(2) . . ?
N3 N2 Co1 120.71(17) . . ?
C12 N3 N2 113.5(2) . . ?
C12 N4 H41 120.0 . . ?
C12 N4 H42 120.0 . . ?
H41 N4 H42 120.0 . . ?
N1 C2 C3 124.5(3) . . ?
N1 C2 H2 117.8 . . ?
C3 C2 H2 117.8 . . ?
C4 C3 C2 119.0(3) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 119.2(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 121.2(3) . . ?
C4 C5 C10 119.2(3) . . ?
C6 C5 C10 119.6(3) . . ?
C7 C6 C5 121.2(3) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 119.6(4) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C9 C8 C7 122.5(3) . . ?
C9 C8 H8 118.7 . . ?
C7 C8 H8 118.7 . . ?
C8 C9 C10 118.3(3) . . ?
C8 C9 C11 114.7(3) . . ?
C10 C9 C11 126.9(3) . . ?
N1 C10 C9 121.2(3) . . ?
N1 C10 C5 120.2(3) . . ?
C9 C10 C5 118.6(3) . . ?
N2 C11 C9 126.5(3) . . ?
N2 C11 H11 116.8 . . ?
C9 C11 H11 116.8 . . ?
N3 C12 N4 118.9(2) . . ?
N3 C12 S1 123.6(2) . . ?
N4 C12 S1 117.5(2) . . ?
C2A N1A C10A 118.2(2) . . ?
C2A N1A Co1 117.6(2) . . ?
C10A N1A Co1 124.18(19) . . ?
C11A N2A N3A 113.9(2) . . ?
C11A N2A Co1 124.8(2) . . ?
N3A N2A Co1 121.27(18) . . ?
C12A N3A N2A 113.1(2) . . ?
C12A N4A H4A1 120.0 . . ?
C12A N4A H4A2 120.0 . . ?
H4A1 N4A H4A2 120.0 . . ?
N1A C2A C3A 124.0(3) . . ?
N1A C2A H2A 118.0 . . ?
C3A C2A H2A 118.0 . . ?
C4A C3A C2A 118.8(3) . . ?
C4A C3A H3A 120.6 . . ?
C2A C3A H3A 120.6 . . ?
C3A C4A C5A 119.7(3) . . ?
C3A C4A H4A 120.2 . . ?
C5A C4A H4A 120.2 . . ?
C4A C5A C6A 120.9(3) . . ?
C4A C5A C10A 119.4(3) . . ?
C6A C5A C10A 119.7(3) . . ?
C7A C6A C5A 120.8(3) . . ?
C7A C6A H6A 119.6 . . ?
C5A C6A H6A 119.6 . . ?
C6A C7A C8A 119.6(3) . . ?
C6A C7A H7A 120.2 . . ?
C8A C7A H7A 120.2 . . ?
C9A C8A C7A 122.5(3) . . ?
C9A C8A H8A 118.7 . . ?
C7A C8A H8A 118.7 . . ?
C8A C9A C10A 118.5(3) . . ?
C8A C9A C11A 114.8(3) . . ?
C10A C9A C11A 126.7(3) . . ?
N1A C10A C5A 119.8(3) . . ?
N1A C10A C9A 121.4(3) . . ?
C5A C10A C9A 118.8(3) . . ?
N2A C11A C9A 127.0(3) . . ?
N2A C11A H11A 116.5 . . ?
C9A C11A H11A 116.5 . . ?
N3A C12A N4A 118.5(3) . . ?
N3A C12A S2 124.1(2) . . ?
N4A C12A S2 117.4(2) . . ?
O4 Cl1 O5 108.2(6) . . ?
O4 Cl1 O2 108.5(5) . . ?
O5 Cl1 O2 113.1(6) . . ?
O4 Cl1 O3 109.4(5) . . ?
O5 Cl1 O3 106.9(4) . . ?
O2 Cl1 O3 110.5(3) . . ?
O1 S3 C13 106.3(2) . . ?
O1 S3 C14 106.1(3) . . ?
C13 S3 C14 105.3(5) . . ?
O1 S3A C14 114.4(8) . . ?
O1 S3A C13 104.7(9) . . ?
C14 S3A C13 107.8(7) . . ?


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
C11 N2 N3 C12 168.2(2) . . . . ?
Co1 N2 N3 C12 -5.4(3) . . . . ?
C10 N1 C2 C3 -1.8(5) . . . . ?
Co1 N1 C2 C3 174.7(3) . . . . ?
N1 C2 C3 C4 0.0(5) . . . . ?
C2 C3 C4 C5 0.9(5) . . . . ?
C3 C4 C5 C6 -177.5(3) . . . . ?
C3 C4 C5 C10 0.1(5) . . . . ?
C4 C5 C6 C7 178.8(4) . . . . ?
C10 C5 C6 C7 1.2(6) . . . . ?
C5 C6 C7 C8 2.1(6) . . . . ?
C6 C7 C8 C9 -2.6(6) . . . . ?
C7 C8 C9 C10 -0.3(5) . . . . ?
C7 C8 C9 C11 177.7(3) . . . . ?
C2 N1 C10 C9 -177.5(3) . . . . ?
Co1 N1 C10 C9 6.2(4) . . . . ?
C2 N1 C10 C5 2.8(4) . . . . ?
Co1 N1 C10 C5 -173.5(2) . . . . ?
C8 C9 C10 N1 -176.1(3) . . . . ?
C11 C9 C10 N1 6.2(5) . . . . ?
C8 C9 C10 C5 3.6(4) . . . . ?
C11 C9 C10 C5 -174.2(3) . . . . ?
C4 C5 C10 N1 -2.0(5) . . . . ?
C6 C5 C10 N1 175.6(3) . . . . ?
C4 C5 C10 C9 178.3(3) . . . . ?
C6 C5 C10 C9 -4.1(5) . . . . ?
N3 N2 C11 C9 178.6(3) . . . . ?
Co1 N2 C11 C9 -8.2(4) . . . . ?
C8 C9 C11 N2 176.6(3) . . . . ?
C10 C9 C11 N2 -5.7(5) . . . . ?
N2 N3 C12 N4 -177.7(2) . . . . ?
N2 N3 C12 S1 1.6(3) . . . . ?
Co1 S1 C12 N3 1.9(2) . . . . ?
Co1 S1 C12 N4 -178.8(2) . . . . ?
C11A N2A N3A C12A 175.7(3) . . . . ?
Co1 N2A N3A C12A -1.2(3) . . . . ?
C10A N1A C2A C3A -3.4(5) . . . . ?
Co1 N1A C2A C3A 175.6(3) . . . . ?
N1A C2A C3A C4A 1.6(5) . . . . ?
C2A C3A C4A C5A 1.3(5) . . . . ?
C3A C4A C5A C6A 176.1(3) . . . . ?
C3A C4A C5A C10A -2.4(5) . . . . ?
C4A C5A C6A C7A -175.9(4) . . . . ?
C10A C5A C6A C7A 2.5(6) . . . . ?
C5A C6A C7A C8A -2.6(6) . . . . ?
C6A C7A C8A C9A 0.1(6) . . . . ?
C7A C8A C9A C10A 2.4(5) . . . . ?
C7A C8A C9A C11A -179.7(3) . . . . ?
C2A N1A C10A C5A 2.2(4) . . . . ?
Co1 N1A C10A C5A -176.7(2) . . . . ?
C2A N1A C10A C9A -175.6(3) . . . . ?
Co1 N1A C10A C9A 5.5(4) . . . . ?
C4A C5A C10A N1A 0.6(5) . . . . ?
C6A C5A C10A N1A -177.8(3) . . . . ?
C4A C5A C10A C9A 178.5(3) . . . . ?
C6A C5A C10A C9A 0.0(5) . . . . ?
C8A C9A C10A N1A 175.5(3) . . . . ?
C11A C9A C10A N1A -2.2(5) . . . . ?
C8A C9A C10A C5A -2.4(5) . . . . ?
C11A C9A C10A C5A 180.0(3) . . . . ?
N3A N2A C11A C9A 178.0(3) . . . . ?
Co1 N2A C11A C9A -5.2(5) . . . . ?
C8A C9A C11A N2A -175.8(3) . . . . ?
C10A C9A C11A N2A 1.9(5) . . . . ?
N2A N3A C12A N4A 179.2(2) . . . . ?
N2A N3A C12A S2 -0.2(4) . . . . ?
Co1 S2 C12A N3A 1.2(3) . . . . ?
Co1 S2 C12A N4A -178.3(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
N4 H41 N3 0.86 2.14 2.990(3) 168.8 2_766
N4 H42 N3A 0.86 2.24 3.061(3) 159.9 2_756
N4A H4A1 O1 0.86 2.08 2.905(4) 159.4 .
N4A H4A2 O4 0.86 2.13 2.983(6) 170.5 .

_refine_diff_density_max         0.527
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.076


