# 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 2017

####################################################################### 
# 
# 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_203K
_database_code_depnum_ccdc_archive 'CCDC 1487305'
_audit_update_record             
;
2017-03-17 deposited with the CCDC.
2017-03-19 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         'C6 Co N6, 2(C3 H4 N S), H3 O'
_chemical_formula_sum            'C12 H11 Co N8 O S2'
_chemical_formula_weight         406.34

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   15.71(6)
_cell_length_b                   8.70(3)
_cell_length_c                   13.25(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1811(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    203(2)
_cell_measurement_reflns_used    488
_cell_measurement_theta_min      1.5369
_cell_measurement_theta_max      27.4855

_exptl_crystal_description       block
_exptl_crystal_colour            light-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_F_000             756
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3500
_exptl_crystal_size_mid          0.2300
_exptl_crystal_size_min          0.2000
_exptl_absorpt_coefficient_mu    1.195
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan

_exptl_absorpt_process_details   
;   Higashi, T.(1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan. 
;
_exptl_absorpt_correction_T_min  0.6782
_exptl_absorpt_correction_T_max  1.0000

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      203(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            12170
_diffrn_reflns_av_unetI/netI     0.1304
_diffrn_reflns_av_R_equivalents  0.1349
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.341
_diffrn_reflns_theta_max         27.523
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4109
_reflns_number_gt                2945
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.914
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1805P)²] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.04(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4109
_refine_ls_number_parameters     218
_refine_ls_number_restraints     133
_refine_ls_R_factor_all          0.1365
_refine_ls_R_factor_gt           0.1198
_refine_ls_wR_factor_ref         0.3222
_refine_ls_wR_factor_gt          0.3049
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.094
_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 0.1950(11) 0.7395(17) 0.4367(13) 0.033(3) Uani 1 1 d . U . . .
C2 C 0.0301(9) 0.8753(16) 0.4291(11) 0.027(3) Uani 1 1 d . U . . .
C3 C -0.0097(10) 0.7255(15) 0.5947(11) 0.026(3) Uani 1 1 d . U . . .
C4 C 0.1232(7) 0.9031(16) 0.5936(9) 0.022(2) Uani 1 1 d . U . . .
C5 C 0.1418(8) 0.5912(18) 0.6061(11) 0.030(3) Uani 1 1 d . U . . .
C6 C 0.0438(9) 0.5672(18) 0.4377(11) 0.029(3) Uani 1 1 d . U . . .
C7 C 0.0316(13) 0.668(2) 0.1641(14) 0.050(4) Uani 1 1 d . U . . .
H7A H -0.0114 0.5944 0.1644 0.060 Uiso 1 1 calc R U . . .
C8 C 0.1618(8) 0.8266(19) 0.1619(12) 0.033(3) Uani 1 1 d . U . . .
H8A H 0.2162 0.8687 0.1600 0.040 Uiso 1 1 calc R U . . .
C9 C 0.0957(7) 0.8966(19) 0.1619(12) 0.032(3) Uani 1 1 d . U . . .
H9A H 0.0943 1.0035 0.1619 0.038 Uiso 1 1 calc R U . . .
C10 C 0.3215(13) 0.319(3) 0.4222(15) 0.052(4) Uani 1 1 d . U . . .
H10A H 0.3745 0.3623 0.4348 0.063 Uiso 1 1 calc R U . . .
C11 C 0.2030(13) 0.2563(19) 0.3282(15) 0.046(4) Uani 1 1 d . U . . .
H11A H 0.1680 0.2539 0.2716 0.056 Uiso 1 1 calc R U . . .
C12 C 0.1865(12) 0.178(2) 0.4216(13) 0.048(4) Uani 1 1 d . U . . .
H12A H 0.1386 0.1189 0.4351 0.057 Uiso 1 1 calc R U . . .
Co1 Co 0.08914(11) 0.73226(17) 0.51524(18) 0.0241(5) Uani 1 1 d . U . . .
N1 N 0.2581(10) 0.7464(14) 0.4012(13) 0.039(3) Uani 1 1 d . U . . .
N2 N -0.0060(9) 0.9692(17) 0.3846(11) 0.039(3) Uani 1 1 d . U . . .
N3 N -0.0733(8) 0.7118(17) 0.6431(12) 0.037(3) Uani 1 1 d . U . . .
N4 N 0.1428(8) 1.0105(16) 0.6407(10) 0.035(3) Uani 1 1 d . U . . .
N5 N 0.1702(9) 0.5099(16) 0.6654(12) 0.043(3) Uani 1 1 d . U . . .
N6 N 0.0094(10) 0.4646(16) 0.3973(11) 0.040(3) Uani 1 1 d . U . . .
N7 N 0.0182(8) 0.8060(19) 0.1620(11) 0.040(3) Uani 1 1 d . U . . .
H7B H -0.0319 0.8455 0.1608 0.048 Uiso 1 1 calc R U . . .
N8 N 0.2783(10) 0.3348(19) 0.3352(11) 0.049(3) Uani 1 1 d . U . . .
H8B H 0.2969 0.3913 0.2867 0.058 Uiso 1 1 calc R U . . .
O1 O 0.4162(7) 0.7730(11) 0.3372(10) 0.033(3) Uani 1 1 d . . . . .
H1A H 0.4463 0.6988 0.3589 0.040 Uiso 1 1 d R U . . .
H1B H 0.3661 0.7644 0.3607 0.040 Uiso 1 1 d R U . . .
H1C H 0.4379 0.8571 0.3572 0.040 Uiso 1 1 d R U . . .
S1 S 0.1356(2) 0.6244(5) 0.1661(4) 0.0459(11) Uani 1 1 d . U . . .
S2 S 0.2681(3) 0.2115(6) 0.5043(4) 0.0552(14) Uani 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.10(2) . ?
C1 Co1 1.962(18) . ?
C2 N2 1.16(2) . ?
C2 Co1 1.926(16) . ?
C3 N3 1.19(2) . ?
C3 Co1 1.877(16) . ?
C4 N4 1.165(19) . ?
C4 Co1 1.891(15) . ?
C5 N5 1.148(19) . ?
C5 Co1 1.907(15) . ?
C6 N6 1.17(2) . ?
C6 Co1 1.904(16) . ?
C7 N7 1.22(3) . ?
C7 S1 1.68(2) . ?
C7 H7A 0.9300 . ?
C8 C9 1.20(2) . ?
C8 S1 1.808(18) . ?
C8 H8A 0.9300 . ?
C9 N7 1.45(2) . ?
C9 H9A 0.9300 . ?
C10 N8 1.34(2) . ?
C10 S2 1.66(2) . ?
C10 H10A 0.9300 . ?
C11 N8 1.37(2) . ?
C11 C12 1.43(2) . ?
C11 H11A 0.9300 . ?
C12 S2 1.711(18) . ?
C12 H12A 0.9300 . ?
N7 H7B 0.8600 . ?
N8 H8B 0.8600 . ?
O1 H1A 0.8499 . ?
O1 H1B 0.8500 . ?
O1 H1C 0.8500 . ?

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 Co1 173.3(17) . . ?
N2 C2 Co1 174.2(14) . . ?
N3 C3 Co1 175.8(13) . . ?
N4 C4 Co1 178.5(12) . . ?
N5 C5 Co1 175.7(14) . . ?
N6 C6 Co1 173.1(14) . . ?
N7 C7 S1 112.9(15) . . ?
N7 C7 H7A 123.5 . . ?
S1 C7 H7A 123.5 . . ?
C9 C8 S1 107.1(12) . . ?
C9 C8 H8A 126.4 . . ?
S1 C8 H8A 126.4 . . ?
C8 C9 N7 116.7(16) . . ?
C8 C9 H9A 121.6 . . ?
N7 C9 H9A 121.6 . . ?
N8 C10 S2 111.4(15) . . ?
N8 C10 H10A 124.3 . . ?
S2 C10 H10A 124.3 . . ?
N8 C11 C12 109.5(16) . . ?
N8 C11 H11A 125.2 . . ?
C12 C11 H11A 125.2 . . ?
C11 C12 S2 109.7(14) . . ?
C11 C12 H12A 125.2 . . ?
S2 C12 H12A 125.2 . . ?
C3 Co1 C4 87.2(6) . . ?
C3 Co1 C6 88.3(6) . . ?
C4 Co1 C6 174.4(6) . . ?
C3 Co1 C5 89.1(6) . . ?
C4 Co1 C5 92.1(7) . . ?
C6 Co1 C5 91.0(7) . . ?
C3 Co1 C2 87.4(6) . . ?
C4 Co1 C2 87.3(6) . . ?
C6 Co1 C2 89.3(7) . . ?
C5 Co1 C2 176.5(6) . . ?
C3 Co1 C1 177.9(7) . . ?
C4 Co1 C1 91.5(6) . . ?
C6 Co1 C1 93.2(7) . . ?
C5 Co1 C1 89.3(7) . . ?
C2 Co1 C1 94.2(7) . . ?
C7 N7 C9 113.0(15) . . ?
C7 N7 H7B 123.5 . . ?
C9 N7 H7B 123.5 . . ?
C10 N8 C11 116.2(15) . . ?
C10 N8 H8B 121.9 . . ?
C11 N8 H8B 121.9 . . ?
H1A O1 H1B 109.0 . . ?
H1A O1 H1C 109.0 . . ?
H1B O1 H1C 109.5 . . ?
C7 S1 C8 90.1(8) . . ?
C10 S2 C12 93.1(10) . . ?

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
S1 C8 C9 N7 -1.9(19) . . . . ?
N8 C11 C12 S2 -1(2) . . . . ?
S1 C7 N7 C9 0.0(19) . . . . ?
C8 C9 N7 C7 1(2) . . . . ?
S2 C10 N8 C11 -3(3) . . . . ?
C12 C11 N8 C10 3(3) . . . . ?
N7 C7 S1 C8 -0.8(14) . . . . ?
C9 C8 S1 C7 1.6(14) . . . . ?
N8 C10 S2 C12 2.1(19) . . . . ?
C11 C12 S2 C10 -0.6(18) . . . . ?

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
N7 H7B N4 0.86 2.16 3.01(2) 166.5 2_574
N8 H8B N5 0.86 1.98 2.83(2) 173.5 3_554
O1 H1A N6 0.85 1.81 2.655(19) 176.4 4_565
O1 H1B N1 0.85 1.79 2.63(2) 176.0 .
O1 H1C N2 0.85 1.79 2.631(19) 171.8 4_575

_refine_diff_density_max         2.700
_refine_diff_density_min         -1.121
_refine_diff_density_rms         0.242

# start Validation Reply Form
_vrf_PLAT341_203K                
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0245 Ang.  
RESPONSE: We have made several attempts to obtain a better full set of data,
however,there is basically no diffraction in the high angles, so the quality 
of the data was poor. 
;
# end Validation Reply Form

####################################################################### 
# 
# 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_293K
_database_code_depnum_ccdc_archive 'CCDC 1487306'
_audit_update_record             
;
2017-03-17 deposited with the CCDC.
2017-03-19 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         'C6 Co N6, 2(C3 H4 N S), H3 O'
_chemical_formula_sum            'C12 H11 Co N8 O S2'
_chemical_formula_weight         406.34


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'
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'
K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mg Mg 0.0486 0.0363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   15.033(14)
_cell_length_b                   8.920(10)
_cell_length_c                   13.208(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1771(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    480
_cell_measurement_theta_min      1.5415
_cell_measurement_theta_max      27.4855

_exptl_crystal_description       block
_exptl_crystal_colour            light-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_F_000             692
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3500
_exptl_crystal_size_mid          0.2300
_exptl_crystal_size_min          0.2000
_exptl_absorpt_coefficient_mu    1.221
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan

_exptl_absorpt_process_details   
;   Higashi, T.(1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan. 
;
_exptl_absorpt_correction_T_min  0.8242
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean 28.6533
_diffrn_reflns_number            12203
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.655
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_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             4032
_reflns_number_gt                3233
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.917
_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.09(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4032
_refine_ls_number_parameters     249
_refine_ls_number_restraints     163
_refine_ls_R_factor_all          0.1095
_refine_ls_R_factor_gt           0.0955
_refine_ls_wR_factor_ref         0.2975
_refine_ls_wR_factor_gt          0.2817
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_restrained_S_all      1.238
_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 0.6100(7) 0.1725(13) 0.2780(10) 0.053(2) Uani 1 1 d . . . . .
C3 C 0.6202(8) -0.1224(13) 0.2752(11) 0.057(3) Uani 1 1 d . . . . .
C4 C 0.7267(7) -0.1211(12) 0.1134(11) 0.052(2) Uani 1 1 d . . . . .
C5 C 0.7713(7) 0.0360(12) 0.2780(10) 0.049(2) Uani 1 1 d . . . . .
C6 C 0.7168(6) 0.1898(12) 0.1142(9) 0.047(2) Uani 1 1 d . . . . .
N7 N 0.496(2) 0.402(5) 0.009(4) 0.093(4) Uani 0.37 1 d . U P A 1
H7A H 0.4889 0.3336 -0.0364 0.111 Uiso 0.37 1 calc R U P A 1
C7 C 0.442(3) 0.415(4) 0.099(3) 0.081(4) Uani 0.37 1 d D U P A 1
H7 H 0.3955 0.3514 0.1168 0.097 Uiso 0.37 1 calc R U P A 1
S1 S 0.4775(14) 0.562(2) 0.1662(16) 0.121(3) Uani 0.37 1 d D U P A 1
C8 C 0.555(3) 0.593(7) 0.077(4) 0.105(4) Uani 0.37 1 d D U P A 1
H8 H 0.5941 0.6729 0.0842 0.126 Uiso 0.37 1 calc R U P A 1
C9 C 0.561(3) 0.514(5) 0.003(4) 0.095(5) Uani 0.37 1 d . U P A 1
H9 H 0.6022 0.5256 -0.0494 0.114 Uiso 0.37 1 calc R U P A 1
N7' N 0.4567(13) 0.413(3) 0.019(2) 0.093(4) Uani 0.63 1 d D U P B 2
H7A' H 0.4298 0.3558 -0.0234 0.111 Uiso 0.63 1 calc R U P B 2
C7' C 0.4638(15) 0.383(2) 0.120(2) 0.081(4) Uani 0.63 1 d D U P B 2
H7' H 0.4411 0.2996 0.1533 0.097 Uiso 0.63 1 calc R U P B 2
S1' S 0.5200(8) 0.5209(13) 0.1718(11) 0.121(3) Uani 0.63 1 d D U P B 2
C8' C 0.5373(17) 0.622(3) 0.070(2) 0.105(4) Uani 0.63 1 d D U P B 2
H8' H 0.5681 0.7127 0.0667 0.126 Uiso 0.63 1 calc R U P B 2
C9' C 0.4985(15) 0.550(3) -0.009(2) 0.095(5) Uani 0.63 1 d D U P B 2
H9' H 0.4991 0.5871 -0.0746 0.114 Uiso 0.63 1 calc R U P B 2
N8 N 0.866(2) 0.668(4) 0.336(2) 0.058(3) Uani 0.37 1 d D U P C 1
H8A H 0.8823 0.7598 0.3337 0.070 Uiso 0.37 1 calc R U P C 1
C10 C 0.776(3) 0.608(3) 0.335(2) 0.086(4) Uani 0.37 1 d D U P C 1
H10 H 0.7238 0.6647 0.3323 0.104 Uiso 0.37 1 calc R U P C 1
S2 S 0.7807(11) 0.414(2) 0.3395(12) 0.111(2) Uani 0.37 1 d D U P C 1
C11 C 0.8862(18) 0.399(4) 0.342(2) 0.071(4) Uani 0.37 1 d D U P C 1
H11 H 0.9204 0.3121 0.3449 0.085 Uiso 0.37 1 calc R U P C 1
C12 C 0.915(3) 0.548(3) 0.340(2) 0.065(4) Uani 0.37 1 d D U P C 1
H12 H 0.9765 0.5631 0.3413 0.078 Uiso 0.37 1 calc R U P C 1
N8' N 0.8872(12) 0.641(2) 0.3363(15) 0.058(3) Uani 0.63 1 d D U P D 2
H8A' H 0.9282 0.7079 0.3359 0.070 Uiso 0.63 1 calc R U P D 2
C10' C 0.8022(14) 0.671(3) 0.3362(13) 0.086(4) Uani 0.63 1 d D U P D 2
H10' H 0.7797 0.7685 0.3357 0.104 Uiso 0.63 1 calc R U P D 2
S2' S 0.7399(7) 0.5221(11) 0.3370(9) 0.111(2) Uani 0.63 1 d D U P D 2
C11' C 0.8383(14) 0.389(2) 0.3376(16) 0.071(4) Uani 0.63 1 d D U P D 2
H11' H 0.8373 0.2850 0.3381 0.085 Uiso 0.63 1 calc R U P D 2
C12' C 0.9059(15) 0.475(2) 0.3373(15) 0.065(4) Uani 0.63 1 d D U P D 2
H12' H 0.9636 0.4369 0.3377 0.078 Uiso 0.63 1 calc R U P D 2
Co1 Co 0.66854(7) 0.02898(12) 0.1934(5) 0.0435(5) Uani 1 1 d . . . . .
N1 N 0.5750(8) 0.2600(13) 0.3251(10) 0.076(4) Uani 1 1 d . . . . .
N2 N 0.4972(8) 0.0049(14) 0.0687(14) 0.070(3) Uani 1 1 d . . . . .
N3 N 0.5906(8) -0.2172(16) 0.3236(11) 0.079(3) Uani 1 1 d . . . . .
N4 N 0.7608(7) -0.2165(12) 0.0714(10) 0.063(2) Uani 1 1 d . . . . .
N5 N 0.8335(6) 0.0387(16) 0.3279(12) 0.073(4) Uani 1 1 d . . . . .
N6 N 0.7468(7) 0.2883(12) 0.0737(11) 0.064(2) Uani 1 1 d . . . . .
O1 O 0.8325(5) 0.5290(9) 0.0151(9) 0.054(2) Uani 1 1 d . . . . .
H1A H 0.8092 0.6106 0.0359 0.064 Uiso 1 1 d R U . . .
H1B H 0.8029 0.4548 0.0379 0.064 Uiso 1 1 d R U . . .
H1C H 0.8853 0.5230 0.0373 0.064 Uiso 1 1 d R U . . .
C2 C 0.5635(9) 0.0191(13) 0.1120(12) 0.060(3) 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 1.128(15) . ?
C1 Co1 1.914(12) . ?
C3 N3 1.150(18) . ?
C3 Co1 1.875(12) . ?
C4 N4 1.138(15) . ?
C4 Co1 1.917(12) . ?
C5 N5 1.144(15) . ?
C5 Co1 1.908(11) . ?
C6 N6 1.124(15) . ?
C6 Co1 1.917(11) . ?
N7 C9 1.40(5) . ?
N7 C7 1.45(7) . ?
N7 H7A 0.8600 . ?
C7 S1 1.67(2) . ?
C7 H7 0.9300 . ?
S1 C8 1.68(3) . ?
C8 C9 1.21(8) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
N7' C7' 1.37(4) . ?
N7' C9' 1.42(2) . ?
N7' H7A' 0.8600 . ?
C7' S1' 1.641(18) . ?
C7' H7' 0.9300 . ?
S1' C8' 1.64(2) . ?
C8' C9' 1.35(3) . ?
C8' H8' 0.9300 . ?
C9' H9' 0.9300 . ?
N8 C12 1.30(2) . ?
N8 C10 1.46(3) . ?
N8 H8A 0.8600 . ?
C10 S2 1.74(3) . ?
C10 H10 0.9300 . ?
S2 C11 1.59(2) . ?
C11 C12 1.40(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
N8' C10' 1.31(2) . ?
N8' C12' 1.51(2) . ?
N8' H8A' 0.8600 . ?
C10' S2' 1.63(2) . ?
C10' H10' 0.9300 . ?
S2' C11' 1.896(19) . ?
C11' C12' 1.27(2) . ?
C11' H11' 0.9300 . ?
C12' H12' 0.9300 . ?
Co1 C2 1.913(13) . ?
N2 C2 1.155(17) . ?
O1 H1A 0.8532 . ?
O1 H1B 0.8525 . ?
O1 H1C 0.8477 . ?

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 Co1 177.7(11) . . ?
N3 C3 Co1 178.6(11) . . ?
N4 C4 Co1 175.4(12) . . ?
N5 C5 Co1 179.0(12) . . ?
N6 C6 Co1 175.3(11) . . ?
C9 N7 C7 112(4) . . ?
C9 N7 H7A 123.8 . . ?
C7 N7 H7A 123.8 . . ?
N7 C7 S1 109(3) . . ?
N7 C7 H7 125.6 . . ?
S1 C7 H7 125.6 . . ?
C7 S1 C8 89(3) . . ?
C9 C8 S1 122(5) . . ?
C9 C8 H8 119.1 . . ?
S1 C8 H8 119.1 . . ?
C8 C9 N7 108(5) . . ?
C8 C9 H9 125.8 . . ?
N7 C9 H9 125.8 . . ?
C7' N7' C9' 113(2) . . ?
C7' N7' H7A' 123.7 . . ?
C9' N7' H7A' 123.7 . . ?
N7' C7' S1' 107.5(18) . . ?
N7' C7' H7' 126.3 . . ?
S1' C7' H7' 126.3 . . ?
C7' S1' C8' 98.7(16) . . ?
C9' C8' S1' 107(2) . . ?
C9' C8' H8' 126.3 . . ?
S1' C8' H8' 126.3 . . ?
C8' C9' N7' 114(3) . . ?
C8' C9' H9' 123.1 . . ?
N7' C9' H9' 123.1 . . ?
C12 N8 C10 103(4) . . ?
C12 N8 H8A 128.3 . . ?
C10 N8 H8A 128.3 . . ?
N8 C10 S2 109(3) . . ?
N8 C10 H10 125.5 . . ?
S2 C10 H10 125.5 . . ?
C11 S2 C10 97.2(18) . . ?
C12 C11 S2 103(3) . . ?
C12 C11 H11 128.3 . . ?
S2 C11 H11 128.3 . . ?
N8 C12 C11 127(4) . . ?
N8 C12 H12 116.5 . . ?
C11 C12 H12 116.5 . . ?
C10' N8' C12' 113(2) . . ?
C10' N8' H8A' 123.6 . . ?
C12' N8' H8A' 123.6 . . ?
N8' C10' S2' 113(2) . . ?
N8' C10' H10' 123.5 . . ?
S2' C10' H10' 123.5 . . ?
C10' S2' C11' 93.5(12) . . ?
C12' C11' S2' 104.5(16) . . ?
C12' C11' H11' 127.8 . . ?
S2' C11' H11' 127.8 . . ?
C11' C12' N8' 116.1(19) . . ?
C11' C12' H12' 121.9 . . ?
N8' C12' H12' 121.9 . . ?
C3 Co1 C5 90.0(5) . . ?
C3 Co1 C2 88.3(6) . . ?
C5 Co1 C2 178.2(6) . . ?
C3 Co1 C1 88.1(5) . . ?
C5 Co1 C1 90.5(5) . . ?
C2 Co1 C1 88.8(5) . . ?
C3 Co1 C4 89.5(5) . . ?
C5 Co1 C4 88.7(5) . . ?
C2 Co1 C4 92.0(5) . . ?
C1 Co1 C4 177.5(5) . . ?
C3 Co1 C6 177.6(5) . . ?
C5 Co1 C6 89.3(4) . . ?
C2 Co1 C6 92.3(5) . . ?
C1 Co1 C6 89.6(4) . . ?
C4 Co1 C6 92.8(5) . . ?
H1A O1 H1B 109.6 . . ?
H1A O1 H1C 109.0 . . ?
H1B O1 H1C 108.5 . . ?
N2 C2 Co1 174.3(14) . . ?

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
C9 N7 C7 S1 0.0(3) . . . . ?
N7 C7 S1 C8 -0.1(2) . . . . ?
C7 S1 C8 C9 0.3(6) . . . . ?
S1 C8 C9 N7 -0.3(8) . . . . ?
C7 N7 C9 C8 0.2(6) . . . . ?
C9' N7' C7' S1' -0.1(3) . . . . ?
N7' C7' S1' C8' -0.2(2) . . . . ?
C7' S1' C8' C9' 0.4(5) . . . . ?
S1' C8' C9' N7' -0.5(7) . . . . ?
C7' N7' C9' C8' 0.4(6) . . . . ?
C12 N8 C10 S2 -0.1(3) . . . . ?
N8 C10 S2 C11 -0.1(2) . . . . ?
C10 S2 C11 C12 0.2(4) . . . . ?
C10 N8 C12 C11 0.4(7) . . . . ?
S2 C11 C12 N8 -0.4(8) . . . . ?
C12' N8' C10' S2' -0.1(3) . . . . ?
N8' C10' S2' C11' 0.0(2) . . . . ?
C10' S2' C11' C12' 0.1(5) . . . . ?
S2' C11' C12' N8' -0.1(7) . . . . ?
C10' N8' C12' C11' 0.2(7) . . . . ?

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
N7 H7A N3 0.86 2.43 3.22(5) 152.9 2_654
N7' H7A' N3 0.86 2.39 3.20(3) 156.8 2_654
N8 H8A N5 0.86 2.59 3.35(4) 146.7 1_565
N8' H8A' N3 0.86 2.45 3.14(2) 137.6 3
O1 H1A N4 0.85 1.77 2.620(14) 176.5 1_565
O1 H1B N6 0.85 1.77 2.621(13) 173.4 .
O1 H1C N2 0.85 1.75 2.594(14) 172.2 3

_refine_diff_density_max         1.249
_refine_diff_density_min         -1.126
_refine_diff_density_rms         0.141

