# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1523010'
_audit_update_record             
;
2017-02-24 deposited with the CCDC.
2017-03-02 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         'C25 H36 N2 O5 S2'
_chemical_formula_sum            'C25 H36 N2 O5 S2'
_chemical_formula_weight         508.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   9.8222(5)
_cell_length_b                   11.7774(6)
_cell_length_c                   13.4213(7)
_cell_angle_alpha                66.426(2)
_cell_angle_beta                 72.546(2)
_cell_angle_gamma                70.537(2)
_cell_volume                     1316.50(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9955
_cell_measurement_theta_min      3.66
_cell_measurement_theta_max      68.94

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    2.139
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.631
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   
; 
SADABS, Bruker AXS Inc., Madison, 
Wisconsin, USA. 
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro focus sealed tube'
_diffrn_radiation_monochromator  'multi layer miror'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27977
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.662
_diffrn_reflns_theta_max         69.323
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4817
_reflns_number_gt                4488
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR-2014 (Burla et al., 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'CAMERON (Betteridge et al., 2003)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_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)+(0.0643P)²+0.5035P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0078(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4817
_refine_ls_number_parameters     317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0940
_refine_ls_wR_factor_gt          0.0920
_refine_ls_goodness_of_fit_ref   0.912
_refine_ls_restrained_S_all      0.912
_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 -0.04282(4) 0.32240(3) 0.25456(4) 0.04154(13) Uani 1 1 d . . . . .
S2 S 0.14708(4) 0.01906(3) 0.37714(3) 0.02999(12) Uani 1 1 d . . . . .
N1 N 0.39550(12) 0.27995(10) 0.20217(9) 0.0245(2) Uani 1 1 d . . . . .
N2 N 0.51602(12) 0.06203(11) 0.35204(9) 0.0274(2) Uani 1 1 d . . . . .
H2 H 0.566(2) 0.0098(18) 0.4016(15) 0.036(4) Uiso 1 1 d . . . . .
O1 O 0.32167(10) 0.10899(10) 0.48373(7) 0.0323(2) Uani 1 1 d . . . . .
O2 O -0.37169(15) 0.48403(14) 0.15525(11) 0.0595(4) Uani 1 1 d . . . . .
O3 O -0.45217(15) 0.54048(11) 0.30723(10) 0.0502(3) Uani 1 1 d . . . . .
O4 O 0.03150(15) -0.24167(11) 0.25217(10) 0.0504(3) Uani 1 1 d . . . . .
O5 O -0.07182(13) -0.33302(10) 0.42769(9) 0.0405(3) Uani 1 1 d . . . . .
C1 C 0.10995(15) 0.22861(13) 0.18612(12) 0.0307(3) Uani 1 1 d . . . . .
C2 C 0.22416(14) 0.13901(12) 0.25548(10) 0.0247(3) Uani 1 1 d . . . . .
H2A H 0.3044 0.0930 0.2087 0.030 Uiso 1 1 calc R U . . .
C3 C 0.29384(13) 0.21224(12) 0.29297(10) 0.0225(3) Uani 1 1 d . . . . .
H3 H 0.2128 0.2765 0.3215 0.027 Uiso 1 1 calc R U . . .
C4 C 0.52512(14) 0.20268(12) 0.16231(11) 0.0247(3) Uani 1 1 d . . . . .
C5 C 0.60151(16) 0.23315(14) 0.05230(11) 0.0309(3) Uani 1 1 d . . . . .
H5 H 0.5614 0.3087 -0.0024 0.037 Uiso 1 1 calc R U . . .
C6 C 0.73530(17) 0.15373(15) 0.02264(12) 0.0369(3) Uani 1 1 d . . . . .
H6 H 0.7865 0.1760 -0.0521 0.044 Uiso 1 1 calc R U . . .
C7 C 0.79514(16) 0.04226(15) 0.10068(13) 0.0375(3) Uani 1 1 d . . . . .
H7 H 0.8871 -0.0112 0.0797 0.045 Uiso 1 1 calc R U . . .
C8 C 0.71960(15) 0.00930(14) 0.20981(12) 0.0322(3) Uani 1 1 d . . . . .
H8 H 0.7590 -0.0677 0.2635 0.039 Uiso 1 1 calc R U . . .
C9 C 0.58678(14) 0.08891(13) 0.24017(11) 0.0254(3) Uani 1 1 d . . . . .
C10 C 0.37797(14) 0.12311(12) 0.38524(10) 0.0247(3) Uani 1 1 d . . . . .
C11 C 0.33981(15) 0.40896(12) 0.12841(11) 0.0285(3) Uani 1 1 d . . . . .
H11A H 0.2862 0.4033 0.0794 0.034 Uiso 1 1 calc R U . . .
H11B H 0.4241 0.4456 0.0810 0.034 Uiso 1 1 calc R U . . .
C12 C 0.23858(17) 0.49695(14) 0.19084(13) 0.0364(3) Uani 1 1 d . . . . .
H12A H 0.1458 0.4709 0.2259 0.055 Uiso 1 1 calc R U . . .
H12B H 0.2190 0.5848 0.1393 0.055 Uiso 1 1 calc R U . . .
H12C H 0.2852 0.4924 0.2479 0.055 Uiso 1 1 calc R U . . .
C13 C 0.1229(2) 0.23964(16) 0.08039(13) 0.0436(4) Uani 1 1 d . . . . .
C14 C 0.2527(3) 0.1608(2) 0.02257(15) 0.0642(6) Uani 1 1 d . . . . .
H14A H 0.3436 0.1799 0.0203 0.096 Uiso 1 1 calc R U . . .
H14B H 0.2408 0.1814 -0.0532 0.096 Uiso 1 1 calc R U . . .
H14C H 0.2580 0.0698 0.0631 0.096 Uiso 1 1 calc R U . . .
C15 C 0.0119(3) 0.3312(2) 0.00954(18) 0.0711(7) Uani 1 1 d . . . . .
H15A H -0.0685 0.3781 0.0531 0.107 Uiso 1 1 calc R U . . .
H15B H -0.0276 0.2834 -0.0157 0.107 Uiso 1 1 calc R U . . .
H15C H 0.0597 0.3917 -0.0548 0.107 Uiso 1 1 calc R U . . .
C16 C -0.19172(17) 0.24779(16) 0.28145(17) 0.0468(4) Uani 1 1 d . . . . .
H16A H -0.2028 0.2452 0.2115 0.056 Uiso 1 1 calc R U . . .
H16B H -0.1695 0.1591 0.3332 0.056 Uiso 1 1 calc R U . . .
C17 C -0.33297(18) 0.32566(16) 0.33182(15) 0.0427(4) Uani 1 1 d . . . . .
H17A H -0.4111 0.2792 0.3567 0.051 Uiso 1 1 calc R U . . .
H17B H -0.3171 0.3337 0.3979 0.051 Uiso 1 1 calc R U . . .
C18 C -0.38465(16) 0.45706(16) 0.25296(14) 0.0381(3) Uani 1 1 d . . . . .
C19 C -0.5154(3) 0.67045(19) 0.2411(2) 0.0668(6) Uani 1 1 d . . . . .
H19A H -0.4631 0.6880 0.1630 0.080 Uiso 1 1 calc R U . . .
H19B H -0.6204 0.6806 0.2435 0.080 Uiso 1 1 calc R U . . .
C20 C -0.5019(3) 0.7598(2) 0.2853(3) 0.0778(7) Uani 1 1 d . . . . .
H20A H -0.5514 0.7404 0.3632 0.117 Uiso 1 1 calc R U . . .
H20B H -0.5476 0.8471 0.2428 0.117 Uiso 1 1 calc R U . . .
H20C H -0.3975 0.7521 0.2795 0.117 Uiso 1 1 calc R U . . .
C21 C 0.10217(16) -0.06409(13) 0.30806(12) 0.0322(3) Uani 1 1 d . . . . .
H21A H 0.0282 -0.0052 0.2621 0.039 Uiso 1 1 calc R U . . .
H21B H 0.1914 -0.0970 0.2592 0.039 Uiso 1 1 calc R U . . .
C22 C 0.04115(18) -0.17364(15) 0.39610(13) 0.0377(3) Uani 1 1 d . . . . .
H22A H 0.1149 -0.2297 0.4431 0.045 Uiso 1 1 calc R U . . .
H22B H -0.0480 -0.1391 0.4440 0.045 Uiso 1 1 calc R U . . .
C23 C 0.00263(15) -0.25161(13) 0.34818(12) 0.0308(3) Uani 1 1 d . . . . .
C24 C -0.12611(19) -0.41100(16) 0.39554(14) 0.0409(4) Uani 1 1 d . . . . .
H24A H -0.0475 -0.4869 0.3866 0.049 Uiso 1 1 calc R U . . .
H24B H -0.1606 -0.3615 0.3246 0.049 Uiso 1 1 calc R U . . .
C25 C -0.2511(2) -0.4507(2) 0.48680(16) 0.0520(4) Uani 1 1 d . . . . .
H25A H -0.2147 -0.5012 0.5560 0.078 Uiso 1 1 calc R U . . .
H25B H -0.2935 -0.5023 0.4680 0.078 Uiso 1 1 calc R U . . .
H25C H -0.3266 -0.3746 0.4960 0.078 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 C1 1.7876(16) . ?
S1 C16 1.8241(16) . ?
S2 C21 1.8090(15) . ?
S2 C2 1.8334(13) . ?
N1 C4 1.3943(17) . ?
N1 C3 1.4635(15) . ?
N1 C11 1.4682(16) . ?
N2 C10 1.3411(17) . ?
N2 C9 1.4065(17) . ?
N2 H2 0.852(19) . ?
O1 C10 1.2360(16) . ?
O2 C18 1.196(2) . ?
O3 C18 1.336(2) . ?
O3 C19 1.458(2) . ?
O4 C23 1.1986(18) . ?
O5 C23 1.3318(17) . ?
O5 C24 1.4476(18) . ?
C1 C13 1.342(2) . ?
C1 C2 1.5133(18) . ?
C2 C3 1.5532(17) . ?
C2 H2A 1.0000 . ?
C3 C10 1.5213(17) . ?
C3 H3 1.0000 . ?
C4 C5 1.4009(18) . ?
C4 C9 1.4047(19) . ?
C5 C6 1.387(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.386(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.390(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.3851(19) . ?
C8 H8 0.9500 . ?
C11 C12 1.508(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C15 1.508(3) . ?
C13 C14 1.512(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.519(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.504(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C19 C20 1.455(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.5136(19) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.500(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C24 C25 1.499(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C16 102.89(7) . . ?
C21 S2 C2 99.32(6) . . ?
C4 N1 C3 115.56(10) . . ?
C4 N1 C11 119.05(10) . . ?
C3 N1 C11 120.15(10) . . ?
C10 N2 C9 123.18(11) . . ?
C10 N2 H2 118.0(12) . . ?
C9 N2 H2 118.6(12) . . ?
C18 O3 C19 116.40(15) . . ?
C23 O5 C24 117.88(12) . . ?
C13 C1 C2 123.00(14) . . ?
C13 C1 S1 122.07(12) . . ?
C2 C1 S1 114.91(10) . . ?
C1 C2 C3 111.91(10) . . ?
C1 C2 S2 111.63(9) . . ?
C3 C2 S2 109.59(8) . . ?
C1 C2 H2A 107.8 . . ?
C3 C2 H2A 107.8 . . ?
S2 C2 H2A 107.8 . . ?
N1 C3 C10 107.66(10) . . ?
N1 C3 C2 112.43(10) . . ?
C10 C3 C2 111.77(10) . . ?
N1 C3 H3 108.3 . . ?
C10 C3 H3 108.3 . . ?
C2 C3 H3 108.3 . . ?
N1 C4 C5 124.98(12) . . ?
N1 C4 C9 116.95(11) . . ?
C5 C4 C9 117.99(12) . . ?
C6 C5 C4 120.45(13) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C6 C5 120.81(13) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 119.53(13) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C9 C8 C7 119.91(14) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C4 121.29(12) . . ?
C8 C9 N2 120.24(12) . . ?
C4 C9 N2 118.30(12) . . ?
O1 C10 N2 122.92(12) . . ?
O1 C10 C3 121.67(11) . . ?
N2 C10 C3 115.41(11) . . ?
N1 C11 C12 112.68(11) . . ?
N1 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
N1 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 C13 C15 123.45(19) . . ?
C1 C13 C14 121.92(16) . . ?
C15 C13 C14 114.63(17) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 S1 108.39(11) . . ?
C17 C16 H16A 110.0 . . ?
S1 C16 H16A 110.0 . . ?
C17 C16 H16B 110.0 . . ?
S1 C16 H16B 110.0 . . ?
H16A C16 H16B 108.4 . . ?
C18 C17 C16 113.34(15) . . ?
C18 C17 H17A 108.9 . . ?
C16 C17 H17A 108.9 . . ?
C18 C17 H17B 108.9 . . ?
C16 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
O2 C18 O3 123.87(16) . . ?
O2 C18 C17 125.32(16) . . ?
O3 C18 C17 110.78(14) . . ?
C20 C19 O3 109.16(18) . . ?
C20 C19 H19A 109.8 . . ?
O3 C19 H19A 109.8 . . ?
C20 C19 H19B 109.8 . . ?
O3 C19 H19B 109.8 . . ?
H19A C19 H19B 108.3 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 S2 107.94(10) . . ?
C22 C21 H21A 110.1 . . ?
S2 C21 H21A 110.1 . . ?
C22 C21 H21B 110.1 . . ?
S2 C21 H21B 110.1 . . ?
H21A C21 H21B 108.4 . . ?
C23 C22 C21 112.73(12) . . ?
C23 C22 H22A 109.0 . . ?
C21 C22 H22A 109.0 . . ?
C23 C22 H22B 109.0 . . ?
C21 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
O4 C23 O5 124.16(14) . . ?
O4 C23 C22 125.62(13) . . ?
O5 C23 C22 110.21(12) . . ?
O5 C24 C25 106.27(13) . . ?
O5 C24 H24A 110.5 . . ?
C25 C24 H24A 110.5 . . ?
O5 C24 H24B 110.5 . . ?
C25 C24 H24B 110.5 . . ?
H24A C24 H24B 108.7 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

_refine_diff_density_max         0.272
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_TF369
_database_code_depnum_ccdc_archive 'CCDC 1522380'
_audit_update_record             
;
2016-12-13 deposited with the CCDC.
2017-03-02 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         'C18 H19 Co N2 O S2'
_chemical_formula_sum            'C18 H19 Co N2 O S2'
_chemical_formula_weight         402.40

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'
S S 0.1246 0.1234 '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'
N N 0.0061 0.0033 '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/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   17.498(4)
_cell_length_b                   5.5628(14)
_cell_length_c                   17.846(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.08(2)
_cell_angle_gamma                90
_cell_volume                     1719.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1883
_cell_measurement_theta_min      3.8090
_cell_measurement_theta_max      26.6070

_exptl_crystal_description       plate
_exptl_crystal_colour            'dark brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.248
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.7b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.740
_exptl_absorpt_correction_T_max  1.689
_exptl_special_details           
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  mirrors
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku mm003 XtaLAB Pro: Kappa '
_diffrn_detector                 'Dectris HPAD Pilatus 200K'
_diffrn_reflns_number            13572
_diffrn_reflns_av_unetI/netI     0.1068
_diffrn_reflns_av_R_equivalents  0.1247
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.518
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_full        25.349
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0410118000
_diffrn_orient_matrix_UB_12      -0.0068884000
_diffrn_orient_matrix_UB_13      -0.0050919000
_diffrn_orient_matrix_UB_21      -0.0013696000
_diffrn_orient_matrix_UB_22      0.0485326000
_diffrn_orient_matrix_UB_23      -0.0370605000
_diffrn_orient_matrix_UB_31      0.0017909000
_diffrn_orient_matrix_UB_32      -0.1182084000
_diffrn_orient_matrix_UB_33      -0.0149071000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      7.00  80.00   0.50   45.00    --    4.40  38.00 -60.00  146
  2  ω    -63.00 -37.00   0.50   45.00    --    4.40 -57.00-180.00   52
  3  ω    -31.00  -5.00   0.50   45.00    --    4.40  57.00 -90.00   52
  4  ω    -75.00 -24.00   0.50   45.00    --   -5.10 -77.00 -30.00  102
  5  ω    -94.00 -45.00   0.50   45.00    --   -5.10 -38.00 -60.00   98
  6  ω    -42.00  83.00   0.50   45.00    --   -5.10 -19.00 120.00  250
;
_diffrn_measurement_method       'ω scans'
_reflns_number_total             3131
_reflns_number_gt                2033
_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       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXLT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3131
_refine_ls_number_parameters     225
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.1189
_refine_ls_wR_factor_gt          0.1048
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_restrained_S_all      0.987
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.40666(4) 0.34623(11) 0.85385(3) 0.0294(2) Uani 1 1 d . . . . .
S1 S 0.38272(7) 0.5526(2) 0.75376(6) 0.0337(3) Uani 1 1 d . . . . .
S2 S 0.52480(7) 0.4338(2) 0.86163(6) 0.0343(3) Uani 1 1 d . . . . .
O1 O 0.52025(19) 0.4901(6) 0.60456(16) 0.0403(8) Uani 1 1 d . . . . .
N2 N 0.4407(2) 0.7376(7) 0.52993(19) 0.0313(9) Uani 1 1 d D . . . .
H2N H 0.448(3) 0.660(7) 0.4898(17) 0.038 Uiso 1 1 d D U . . .
N1 N 0.3994(2) 0.9744(7) 0.65300(19) 0.0346(9) Uani 1 1 d D . . . .
H1N H 0.398(3) 1.085(6) 0.6876(19) 0.042 Uiso 1 1 d D U . . .
C3 C 0.3911(3) 0.9379(8) 0.5173(2) 0.0280(10) Uani 1 1 d . . . . .
C8 C 0.3727(3) 1.0630(8) 0.5802(2) 0.0292(10) Uani 1 1 d . . . . .
C2' C 0.3967(3) 0.0176(8) 0.9021(3) 0.0371(12) Uani 1 1 d . . . . .
H2' H 0.4300 -0.1149 0.8977 0.045 Uiso 1 1 calc R U . . .
C10 C 0.5353(3) 0.6217(8) 0.7858(2) 0.0331(11) Uani 1 1 d . . . . .
C2 C 0.4772(3) 0.6688(8) 0.5973(2) 0.0310(10) Uani 1 1 d . . . . .
C1 C 0.4689(3) 0.8268(8) 0.6657(2) 0.0355(11) Uani 1 1 d . . . . .
H1 H 0.5144 0.9373 0.6737 0.043 Uiso 1 1 calc R U . . .
C4 C 0.3604(3) 1.0062(9) 0.4453(2) 0.0401(12) Uani 1 1 d . . . . .
H4 H 0.3730 0.9188 0.4029 0.048 Uiso 1 1 calc R U . . .
C9 C 0.4698(3) 0.6742(8) 0.7372(2) 0.0325(11) Uani 1 1 d . . . . .
C6 C 0.2926(3) 1.3294(8) 0.4963(3) 0.0373(11) Uani 1 1 d . . . . .
H6 H 0.2591 1.4643 0.4891 0.045 Uiso 1 1 calc R U . . .
C1' C 0.3283(3) 0.0713(8) 0.8526(3) 0.0404(12) Uani 1 1 d . . . . .
H1' H 0.3074 -0.0211 0.8098 0.048 Uiso 1 1 calc R U . . .
C11 C 0.6171(3) 0.7038(9) 0.7791(3) 0.0407(13) Uani 1 1 d . . . . .
H11 H 0.6140 0.8259 0.7377 0.049 Uiso 1 1 calc R U . . .
C7 C 0.3231(3) 1.2590(8) 0.5688(3) 0.0365(12) Uani 1 1 d . . . . .
H7 H 0.3099 1.3452 0.6112 0.044 Uiso 1 1 calc R U . . .
C5' C 0.2961(3) 0.2852(8) 0.8775(3) 0.0401(12) Uani 1 1 d . . . . .
H5' H 0.2504 0.3631 0.8544 0.048 Uiso 1 1 calc R U . . .
C4' C 0.3453(3) 0.3621(9) 0.9438(3) 0.0395(12) Uani 1 1 d . . . . .
H4' H 0.3382 0.5014 0.9729 0.047 Uiso 1 1 calc R U . . .
C5 C 0.3109(3) 1.2034(8) 0.4341(3) 0.0411(13) Uani 1 1 d . . . . .
H5 H 0.2899 1.2509 0.3844 0.049 Uiso 1 1 calc R U . . .
C3' C 0.4068(3) 0.1948(8) 0.9590(2) 0.0384(12) Uani 1 1 d . . . . .
H3' H 0.4475 0.2013 1.0002 0.046 Uiso 1 1 calc R U . . .
C13 C 0.6567(3) 0.8214(9) 0.8518(3) 0.0473(14) Uani 1 1 d . . . . .
H13A H 0.6258 0.9581 0.8648 0.071 Uiso 1 1 calc R U . . .
H13B H 0.7081 0.8776 0.8441 0.071 Uiso 1 1 calc R U . . .
H13C H 0.6616 0.7037 0.8931 0.071 Uiso 1 1 calc R U . . .
C12 C 0.6652(3) 0.4888(9) 0.7566(3) 0.0442(13) Uani 1 1 d . . . . .
H12A H 0.6660 0.3614 0.7946 0.066 Uiso 1 1 calc R U . . .
H12B H 0.7181 0.5419 0.7537 0.066 Uiso 1 1 calc R U . . .
H12C H 0.6421 0.4269 0.7071 0.066 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 C2' 2.039(5) . ?
Co1 C1' 2.053(5) . ?
Co1 C4' 2.055(4) . ?
Co1 C3' 2.057(4) . ?
Co1 C5' 2.065(5) . ?
Co1 S2 2.1093(14) . ?
Co1 S1 2.1149(13) . ?
S1 C9 1.731(5) . ?
S2 C10 1.740(4) . ?
O1 C2 1.242(5) . ?
N2 C2 1.336(5) . ?
N2 C3 1.410(6) . ?
N2 H2N 0.860(19) . ?
N1 C8 1.407(5) . ?
N1 C1 1.458(6) . ?
N1 H1N 0.874(19) . ?
C3 C4 1.375(6) . ?
C3 C8 1.397(6) . ?
C8 C7 1.391(6) . ?
C2' C3' 1.408(6) . ?
C2' C1' 1.417(7) . ?
C2' H2' 0.9500 . ?
C10 C9 1.367(6) . ?
C10 C11 1.523(7) . ?
C2 C1 1.526(6) . ?
C1 C9 1.532(6) . ?
C1 H1 1.0000 . ?
C4 C5 1.395(7) . ?
C4 H4 0.9500 . ?
C6 C7 1.386(6) . ?
C6 C5 1.387(6) . ?
C6 H6 0.9500 . ?
C1' C5' 1.414(6) . ?
C1' H1' 0.9500 . ?
C11 C13 1.530(7) . ?
C11 C12 1.548(7) . ?
C11 H11 1.0000 . ?
C7 H7 0.9500 . ?
C5' C4' 1.429(7) . ?
C5' H5' 0.9500 . ?
C4' C3' 1.419(7) . ?
C4' H4' 0.9500 . ?
C5 H5 0.9500 . ?
C3' H3' 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2' Co1 C1' 40.53(19) . . ?
C2' Co1 C4' 67.87(19) . . ?
C1' Co1 C4' 67.6(2) . . ?
C2' Co1 C3' 40.21(18) . . ?
C1' Co1 C3' 67.6(2) . . ?
C4' Co1 C3' 40.37(19) . . ?
C2' Co1 C5' 68.18(19) . . ?
C1' Co1 C5' 40.17(18) . . ?
C4' Co1 C5' 40.58(19) . . ?
C3' Co1 C5' 68.1(2) . . ?
C2' Co1 S2 108.68(15) . . ?
C1' Co1 S2 145.10(15) . . ?
C4' Co1 S2 123.58(15) . . ?
C3' Co1 S2 99.16(15) . . ?
C5' Co1 S2 164.16(14) . . ?
C2' Co1 S1 145.60(14) . . ?
C1' Co1 S1 110.03(15) . . ?
C4' Co1 S1 124.99(15) . . ?
C3' Co1 S1 165.35(15) . . ?
C5' Co1 S1 100.46(14) . . ?
S2 Co1 S1 90.36(5) . . ?
C9 S1 Co1 106.35(16) . . ?
C10 S2 Co1 107.27(17) . . ?
C2 N2 C3 125.2(4) . . ?
C2 N2 H2N 120(3) . . ?
C3 N2 H2N 115(3) . . ?
C8 N1 C1 120.1(3) . . ?
C8 N1 H1N 112(3) . . ?
C1 N1 H1N 113(3) . . ?
C4 C3 C8 120.6(4) . . ?
C4 C3 N2 121.3(4) . . ?
C8 C3 N2 118.1(4) . . ?
C7 C8 C3 118.9(4) . . ?
C7 C8 N1 121.9(4) . . ?
C3 C8 N1 118.9(4) . . ?
C3' C2' C1' 108.1(4) . . ?
C3' C2' Co1 70.6(2) . . ?
C1' C2' Co1 70.3(3) . . ?
C3' C2' H2' 125.9 . . ?
C1' C2' H2' 125.9 . . ?
Co1 C2' H2' 124.8 . . ?
C9 C10 C11 126.8(4) . . ?
C9 C10 S2 116.8(4) . . ?
C11 C10 S2 116.4(3) . . ?
O1 C2 N2 121.9(4) . . ?
O1 C2 C1 120.1(4) . . ?
N2 C2 C1 117.8(4) . . ?
N1 C1 C2 111.8(4) . . ?
N1 C1 C9 110.6(4) . . ?
C2 C1 C9 110.8(4) . . ?
N1 C1 H1 107.8 . . ?
C2 C1 H1 107.8 . . ?
C9 C1 H1 107.8 . . ?
C3 C4 C5 120.3(4) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C10 C9 C1 123.8(4) . . ?
C10 C9 S1 119.2(3) . . ?
C1 C9 S1 116.9(3) . . ?
C7 C6 C5 120.1(4) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C5' C1' C2' 108.7(4) . . ?
C5' C1' Co1 70.4(3) . . ?
C2' C1' Co1 69.2(3) . . ?
C5' C1' H1' 125.7 . . ?
C2' C1' H1' 125.7 . . ?
Co1 C1' H1' 126.3 . . ?
C10 C11 C13 112.4(4) . . ?
C10 C11 C12 109.9(4) . . ?
C13 C11 C12 110.6(4) . . ?
C10 C11 H11 107.9 . . ?
C13 C11 H11 107.9 . . ?
C12 C11 H11 107.9 . . ?
C6 C7 C8 120.5(4) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C1' C5' C4' 107.0(5) . . ?
C1' C5' Co1 69.4(3) . . ?
C4' C5' Co1 69.3(3) . . ?
C1' C5' H5' 126.5 . . ?
C4' C5' H5' 126.5 . . ?
Co1 C5' H5' 126.3 . . ?
C3' C4' C5' 108.3(4) . . ?
C3' C4' Co1 69.9(3) . . ?
C5' C4' Co1 70.1(3) . . ?
C3' C4' H4' 125.8 . . ?
C5' C4' H4' 125.8 . . ?
Co1 C4' H4' 125.8 . . ?
C6 C5 C4 119.5(4) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C2' C3' C4' 107.9(4) . . ?
C2' C3' Co1 69.2(3) . . ?
C4' C3' Co1 69.7(2) . . ?
C2' C3' H3' 126.1 . . ?
C4' C3' H3' 126.1 . . ?
Co1 C3' H3' 126.6 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N2 C3 C4 175.1(4) . . . . ?
C2 N2 C3 C8 -6.1(6) . . . . ?
C4 C3 C8 C7 -0.3(7) . . . . ?
N2 C3 C8 C7 -179.1(4) . . . . ?
C4 C3 C8 N1 174.1(4) . . . . ?
N2 C3 C8 N1 -4.7(6) . . . . ?
C1 N1 C8 C7 -159.7(4) . . . . ?
C1 N1 C8 C3 26.0(6) . . . . ?
Co1 S2 C10 C9 -0.7(4) . . . . ?
Co1 S2 C10 C11 -178.7(3) . . . . ?
C3 N2 C2 O1 -179.9(4) . . . . ?
C3 N2 C2 C1 -4.0(7) . . . . ?
C8 N1 C1 C2 -34.0(6) . . . . ?
C8 N1 C1 C9 -158.0(4) . . . . ?
O1 C2 C1 N1 -161.2(4) . . . . ?
N2 C2 C1 N1 22.8(6) . . . . ?
O1 C2 C1 C9 -37.3(6) . . . . ?
N2 C2 C1 C9 146.7(4) . . . . ?
C8 C3 C4 C5 0.6(7) . . . . ?
N2 C3 C4 C5 179.3(4) . . . . ?
C11 C10 C9 C1 0.6(7) . . . . ?
S2 C10 C9 C1 -177.1(3) . . . . ?
C11 C10 C9 S1 177.7(4) . . . . ?
S2 C10 C9 S1 -0.1(5) . . . . ?
N1 C1 C9 C10 -143.9(4) . . . . ?
C2 C1 C9 C10 91.5(5) . . . . ?
N1 C1 C9 S1 39.0(5) . . . . ?
C2 C1 C9 S1 -85.5(4) . . . . ?
Co1 S1 C9 C10 0.8(4) . . . . ?
Co1 S1 C9 C1 178.1(3) . . . . ?
C3' C2' C1' C5' 1.2(5) . . . . ?
Co1 C2' C1' C5' -59.5(3) . . . . ?
C3' C2' C1' Co1 60.7(3) . . . . ?
C9 C10 C11 C13 128.3(5) . . . . ?
S2 C10 C11 C13 -54.0(5) . . . . ?
C9 C10 C11 C12 -108.1(5) . . . . ?
S2 C10 C11 C12 69.7(4) . . . . ?
C5 C6 C7 C8 0.5(7) . . . . ?
C3 C8 C7 C6 -0.2(7) . . . . ?
N1 C8 C7 C6 -174.5(4) . . . . ?
C2' C1' C5' C4' -0.6(5) . . . . ?
Co1 C1' C5' C4' -59.4(3) . . . . ?
C2' C1' C5' Co1 58.8(3) . . . . ?
C1' C5' C4' C3' -0.2(5) . . . . ?
Co1 C5' C4' C3' -59.7(3) . . . . ?
C1' C5' C4' Co1 59.5(3) . . . . ?
C7 C6 C5 C4 -0.3(7) . . . . ?
C3 C4 C5 C6 -0.3(7) . . . . ?
C1' C2' C3' C4' -1.3(5) . . . . ?
Co1 C2' C3' C4' 59.2(3) . . . . ?
C1' C2' C3' Co1 -60.5(3) . . . . ?
C5' C4' C3' C2' 0.9(5) . . . . ?
Co1 C4' C3' C2' -58.9(3) . . . . ?
C5' C4' C3' Co1 59.8(3) . . . . ?

_refine_diff_density_max         0.517
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.097




_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile / water'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1523011'
_audit_update_record             
;
2016-12-15 deposited with the CCDC.
2017-03-02 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         'C42 H50 Co2 N4 O2 S4, 1.5 (C5 H12)'
_chemical_formula_sum            'C43.67 H54 Co2 N4 O2 S4'
_chemical_formula_weight         913.01

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

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   32.4643(17)
_cell_length_b                   32.4643(17)
_cell_length_c                   10.4380(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     9527.1(11)
_cell_formula_units_Z            9
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5920
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      29.8

_exptl_crystal_description       needle
_exptl_crystal_colour            dark
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_F_000             4302
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    1.023
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.691
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   
;
SADABS, Bruker AXS Inc., Madison, 
Wisconsin, USA. or Sheldrick, G. M. (1996)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23401
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.430
_diffrn_reflns_theta_max         29.984
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6170
_reflns_number_gt                4543
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'Bruker APEX2'
_computing_cell_refinement       'Bruke SAINT'
_computing_data_reduction        'Bruke SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_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)+(0.0570P)²+3.7884P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6170
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.1020
_refine_ls_wR_factor_gt          0.0909
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_restrained_S_all      0.980
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.11289(2) 0.31701(2) 0.27601(2) 0.02613(8) Uani 1 1 d . . . . .
S1 S 0.15406(2) 0.34996(2) 0.45454(4) 0.02461(10) Uani 1 1 d . . . . .
S2 S 0.14197(2) 0.38918(2) 0.18694(4) 0.03263(12) Uani 1 1 d . . . . .
O1 O 0.06295(5) 0.34208(5) 0.62705(14) 0.0407(4) Uani 1 1 d . . . . .
N1 N 0.12441(6) 0.40787(6) 0.71880(14) 0.0309(4) Uani 1 1 d . . . . .
N2 N 0.12008(6) 0.45476(6) 0.50549(14) 0.0311(4) Uani 1 1 d . . . . .
C1 C 0.16157(6) 0.41010(6) 0.44329(16) 0.0249(4) Uani 1 1 d . . . . .
H1 H 0.1877 0.4315 0.5030 0.030 Uiso 1 1 calc R U . . .
C2 C 0.17544(7) 0.42974(7) 0.30976(16) 0.0269(4) Uani 1 1 d . . . . .
C3 C 0.20911(7) 0.47452(7) 0.28130(19) 0.0338(4) Uani 1 1 d . . . . .
C4 C 0.23975(8) 0.51208(8) 0.3768(2) 0.0432(5) Uani 1 1 d . . . . .
H4A H 0.2318 0.4988 0.4635 0.065 Uiso 1 1 calc R U . . .
H4B H 0.2342 0.5390 0.3699 0.065 Uiso 1 1 calc R U . . .
H4C H 0.2733 0.5229 0.3592 0.065 Uiso 1 1 calc R U . . .
C5 C 0.21944(10) 0.49186(9) 0.1437(2) 0.0540(7) Uani 1 1 d . . . . .
H5A H 0.2141 0.4655 0.0874 0.081 Uiso 1 1 calc R U . . .
H5B H 0.2526 0.5174 0.1364 0.081 Uiso 1 1 calc R U . . .
H5C H 0.1983 0.5039 0.1185 0.081 Uiso 1 1 calc R U . . .
C6 C 0.11459(7) 0.40784(7) 0.48853(17) 0.0274(4) Uani 1 1 d . . . . .
H6 H 0.0895 0.3903 0.4225 0.033 Uiso 1 1 calc R U . . .
C7 C 0.09725(7) 0.38183(7) 0.61645(17) 0.0301(4) Uani 1 1 d . . . . .
C8 C 0.15590(7) 0.45741(7) 0.70759(17) 0.0291(4) Uani 1 1 d . . . . .
C9 C 0.18849(8) 0.48256(8) 0.8038(2) 0.0392(5) Uani 1 1 d . . . . .
H9 H 0.1925 0.4658 0.8728 0.047 Uiso 1 1 calc R U . . .
C10 C 0.21513(9) 0.53159(9) 0.8003(2) 0.0472(6) Uani 1 1 d . . . . .
H10 H 0.2378 0.5484 0.8657 0.057 Uiso 1 1 calc R U . . .
C11 C 0.20875(8) 0.55612(8) 0.7012(2) 0.0436(5) Uani 1 1 d . . . . .
H11 H 0.2261 0.5899 0.7002 0.052 Uiso 1 1 calc R U . . .
C12 C 0.17683(8) 0.53129(8) 0.6028(2) 0.0371(5) Uani 1 1 d . . . . .
H12 H 0.1727 0.5484 0.5350 0.045 Uiso 1 1 calc R U . . .
C13 C 0.15096(7) 0.48174(7) 0.60255(17) 0.0292(4) Uani 1 1 d . . . . .
C14 C 0.11576(9) 0.38492(9) 0.84403(18) 0.0414(5) Uani 1 1 d . . . . .
H14A H 0.0846 0.3558 0.8438 0.062 Uiso 1 1 calc R U . . .
H14B H 0.1162 0.4066 0.9101 0.062 Uiso 1 1 calc R U . . .
H14C H 0.1406 0.3770 0.8622 0.062 Uiso 1 1 calc R U . . .
C15 C 0.10952(8) 0.47701(8) 0.3977(2) 0.0401(5) Uani 1 1 d . . . . .
H15A H 0.0953 0.4537 0.3271 0.048 Uiso 1 1 calc R U . . .
H15B H 0.1396 0.5042 0.3658 0.048 Uiso 1 1 calc R U . . .
C16 C 0.07581(8) 0.49436(9) 0.4350(3) 0.0507(6) Uani 1 1 d . . . . .
H16A H 0.0461 0.4676 0.4673 0.076 Uiso 1 1 calc R U . . .
H16B H 0.0690 0.5081 0.3599 0.076 Uiso 1 1 calc R U . . .
H16C H 0.0904 0.5186 0.5020 0.076 Uiso 1 1 calc R U . . .
C17 C 0.04405(7) 0.30520(8) 0.2548(2) 0.0429(5) Uani 1 1 d . . . . .
H17 H 0.0356 0.3292 0.2490 0.052 Uiso 1 1 calc R U . . .
C18 C 0.04672(7) 0.28345(8) 0.3678(2) 0.0417(5) Uani 1 1 d . . . . .
H18 H 0.0404 0.2901 0.4518 0.050 Uiso 1 1 calc R U . . .
C19 C 0.06033(8) 0.25013(8) 0.3353(2) 0.0451(6) Uani 1 1 d . . . . .
H19 H 0.0652 0.2305 0.3937 0.054 Uiso 1 1 calc R U . . .
C20 C 0.06551(8) 0.25069(8) 0.2017(2) 0.0476(6) Uani 1 1 d . . . . .
H20 H 0.0739 0.2311 0.1539 0.057 Uiso 1 1 calc R U . . .
C21 C 0.05615(8) 0.28528(9) 0.1508(2) 0.0471(6) Uani 1 1 d . . . . .
H21 H 0.0577 0.2937 0.0630 0.056 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 C21 2.066(2) . ?
Co1 C20 2.072(2) . ?
Co1 C19 2.075(2) . ?
Co1 C17 2.082(2) . ?
Co1 C18 2.092(2) . ?
Co1 S1 2.2301(5) . ?
Co1 S2 2.2435(6) . ?
Co1 S1 2.2606(5) 16 ?
S1 C1 1.8465(18) . ?
S1 Co1 2.2606(5) 16 ?
S2 C2 1.7685(18) . ?
O1 C7 1.217(2) . ?
N1 C7 1.374(2) . ?
N1 C8 1.415(3) . ?
N1 C14 1.461(2) . ?
N2 C13 1.386(2) . ?
N2 C6 1.453(2) . ?
N2 C15 1.467(2) . ?
C1 C2 1.505(2) . ?
C1 C6 1.563(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.344(3) . ?
C3 C4 1.502(3) . ?
C3 C5 1.517(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.529(3) . ?
C6 H6 1.0000 . ?
C8 C9 1.390(3) . ?
C8 C13 1.407(3) . ?
C9 C10 1.381(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.394(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.393(3) . ?
C12 H12 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.511(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.399(3) . ?
C17 C21 1.417(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.399(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.404(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.406(4) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 Co1 C20 39.75(10) . . ?
C21 Co1 C19 66.75(10) . . ?
C20 Co1 C19 39.58(10) . . ?
C21 Co1 C17 39.95(9) . . ?
C20 Co1 C17 66.30(9) . . ?
C19 Co1 C17 66.02(9) . . ?
C21 Co1 C18 66.59(9) . . ?
C20 Co1 C18 66.09(9) . . ?
C19 Co1 C18 39.24(9) . . ?
C17 Co1 C18 39.15(9) . . ?
C21 Co1 S1 159.94(7) . . ?
C20 Co1 S1 140.07(8) . . ?
C19 Co1 S1 103.57(7) . . ?
C17 Co1 S1 120.51(7) . . ?
C18 Co1 S1 94.61(6) . . ?
C21 Co1 S2 93.62(8) . . ?
C20 Co1 S2 129.53(8) . . ?
C19 Co1 S2 155.94(7) . . ?
C17 Co1 S2 90.04(7) . . ?
C18 Co1 S2 121.32(7) . . ?
S1 Co1 S2 90.401(19) . . ?
C21 Co1 S1 115.18(7) . 16 ?
C20 Co1 S1 95.68(7) . 16 ?
C19 Co1 S1 111.74(7) . 16 ?
C17 Co1 S1 154.95(7) . 16 ?
C18 Co1 S1 149.94(7) . 16 ?
S1 Co1 S1 84.522(18) . 16 ?
S2 Co1 S1 88.74(2) . 16 ?
C1 S1 Co1 100.64(6) . . ?
C1 S1 Co1 111.33(6) . 16 ?
Co1 S1 Co1 95.478(18) . 16 ?
C2 S2 Co1 104.97(6) . . ?
C7 N1 C8 120.78(16) . . ?
C7 N1 C14 118.78(18) . . ?
C8 N1 C14 119.95(16) . . ?
C13 N2 C6 114.98(15) . . ?
C13 N2 C15 121.51(17) . . ?
C6 N2 C15 119.09(15) . . ?
C2 C1 C6 112.22(15) . . ?
C2 C1 S1 111.11(12) . . ?
C6 C1 S1 108.74(12) . . ?
C2 C1 H1 108.2 . . ?
C6 C1 H1 108.2 . . ?
S1 C1 H1 108.2 . . ?
C3 C2 C1 124.89(17) . . ?
C3 C2 S2 120.64(15) . . ?
C1 C2 S2 114.43(13) . . ?
C2 C3 C4 125.56(18) . . ?
C2 C3 C5 121.31(19) . . ?
C4 C3 C5 113.12(18) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 C7 106.91(14) . . ?
N2 C6 C1 112.48(15) . . ?
C7 C6 C1 111.78(15) . . ?
N2 C6 H6 108.5 . . ?
C7 C6 H6 108.5 . . ?
C1 C6 H6 108.5 . . ?
O1 C7 N1 123.18(18) . . ?
O1 C7 C6 123.65(18) . . ?
N1 C7 C6 113.16(17) . . ?
C9 C8 C13 120.04(19) . . ?
C9 C8 N1 120.88(18) . . ?
C13 C8 N1 118.85(17) . . ?
C10 C9 C8 120.8(2) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 119.8(2) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C10 C11 C12 120.0(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 120.9(2) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
N2 C13 C12 123.99(18) . . ?
N2 C13 C8 117.67(17) . . ?
C12 C13 C8 118.34(18) . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 C16 112.14(18) . . ?
N2 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
N2 C15 H15B 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C21 108.3(2) . . ?
C18 C17 Co1 70.83(12) . . ?
C21 C17 Co1 69.41(12) . . ?
C18 C17 H17 125.8 . . ?
C21 C17 H17 125.8 . . ?
Co1 C17 H17 125.5 . . ?
C17 C18 C19 108.1(2) . . ?
C17 C18 Co1 70.02(13) . . ?
C19 C18 Co1 69.70(13) . . ?
C17 C18 H18 126.0 . . ?
C19 C18 H18 126.0 . . ?
Co1 C18 H18 125.9 . . ?
C18 C19 C20 108.2(2) . . ?
C18 C19 Co1 71.06(13) . . ?
C20 C19 Co1 70.09(13) . . ?
C18 C19 H19 125.9 . . ?
C20 C19 H19 125.9 . . ?
Co1 C19 H19 124.6 . . ?
C21 C20 C19 108.3(2) . . ?
C21 C20 Co1 69.90(12) . . ?
C19 C20 Co1 70.33(12) . . ?
C21 C20 H20 125.9 . . ?
C19 C20 H20 125.9 . . ?
Co1 C20 H20 125.5 . . ?
C20 C21 C17 107.1(2) . . ?
C20 C21 Co1 70.35(12) . . ?
C17 C21 Co1 70.64(12) . . ?
C20 C21 H21 126.4 . . ?
C17 C21 H21 126.4 . . ?
Co1 C21 H21 124.2 . . ?

_refine_diff_density_max         0.453
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.067



####################################################################### 
# 
# 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_TF343
_database_code_depnum_ccdc_archive 'CCDC 1522379'
_audit_update_record             
;
2016-12-13 deposited with the CCDC.
2017-03-02 downloaded from the CCDC.
;
_audit_creation_date             2016-12-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3368 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H15 Co N2 O S2'
_chemical_formula_sum            'C18 H15 Co N2 O S2'
_chemical_formula_weight         398.37
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.1653(2)
_cell_length_b                   19.6347(6)
_cell_length_c                   16.9400(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.169(2)
_cell_angle_gamma                90
_cell_volume                     3367.36(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    20591
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.8350
_cell_measurement_theta_min      3.8590
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.274
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.7b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark brown'
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            54264
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.742
_diffrn_reflns_theta_min         3.649
_diffrn_ambient_temperature      173.15
_diffrn_detector                 'HPAD Dectris Pilatus200K'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.9964
_diffrn_measured_fraction_theta_max 0.9202
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     56.00  88.00   0.50    9.09    --   -0.30  38.00-150.00   64
  2  ω    -23.00  28.00   0.50    9.09    --   -0.30  38.00 -90.00  102
  3  ω    -19.00  89.00   0.50    9.09    --   -0.30  19.00 120.00  216
  4  ω     -7.00  73.00   0.50    9.09    --   -0.30  38.00 -60.00  160
  5  ω     27.00  87.00   0.50    9.09    --   -0.30  38.00-180.00  120
  6  ω     37.00  74.00   0.50    9.09    --   -0.30  38.00 -30.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0346479000
_diffrn_orient_matrix_UB_12      -0.0270376000
_diffrn_orient_matrix_UB_13      0.0166315000
_diffrn_orient_matrix_UB_21      -0.0608417000
_diffrn_orient_matrix_UB_22      0.0151042000
_diffrn_orient_matrix_UB_23      -0.0143856000
_diffrn_orient_matrix_UB_31      0.0009964000
_diffrn_orient_matrix_UB_32      -0.0186253000
_diffrn_orient_matrix_UB_33      -0.0358370000
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Rigaku mm003 (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8636
_reflns_number_total             9670
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         9665
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0242
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0344P)²+1.0027P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0634
_refine_ls_wR_factor_ref         0.0652
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C3'B(H3'B), C1'B(H1'B), C2'B(H2'B), C4(H4), C4'B(H4'B), C6(H6),
 C5'B(H5'B), C5'(H5'), C5(H5), C4B(H4B), C3'(H3'), C5B(H5B), C2'(H2'), C1'(H1'),
  C4'(H4'), C7B(H7B), C6B(H6B)
2.b Idealised Me refined as rotating group:
 C13B(H13D,H13E,H13F), C12B(H12D,H12E,H12F), C13(H13A,H13B,H13C), C12(H12A,
 H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.19806(2) 0.71812(2) 0.25068(2) 0.01759(4) Uani 1 1 d . . . . .
Co1B Co 0.24723(2) 0.43718(2) 0.82101(2) 0.01994(4) Uani 1 1 d . . . . .
S1 S 0.35063(3) 0.65645(2) 0.30538(2) 0.01850(6) Uani 1 1 d . . . . .
S2 S 0.10474(3) 0.72677(2) 0.35708(2) 0.02216(6) Uani 1 1 d . . . . .
S1B S 0.42452(3) 0.40246(2) 0.88289(2) 0.02115(6) Uani 1 1 d . . . . .
S2B S 0.16911(3) 0.46699(2) 0.92768(2) 0.03012(8) Uani 1 1 d . . . . .
O1 O 0.23535(9) 0.62555(5) 0.55380(5) 0.02497(18) Uani 1 1 d . . . . .
O1B O 0.37655(10) 0.44896(6) 1.14188(6) 0.0330(2) Uani 1 1 d . . . . .
N1 N 0.53089(10) 0.60540(5) 0.45114(6) 0.02055(19) Uani 1 1 d . . . . .
N2 N 0.43013(10) 0.57937(5) 0.59907(6) 0.02110(19) Uani 1 1 d . . . . .
N1B N 0.60201(10) 0.35584(6) 1.02782(6) 0.0241(2) Uani 1 1 d . . . . .
N2B N 0.55760(10) 0.39084(6) 1.18556(6) 0.0227(2) Uani 1 1 d . . . . .
C1B C 0.49964(11) 0.39258(6) 1.04401(7) 0.0187(2) Uani 1 1 d . . . . .
C9 C 0.31791(11) 0.65320(6) 0.40355(6) 0.01659(19) Uani 1 1 d . . . . .
C1 C 0.40912(11) 0.62159(5) 0.46438(6) 0.01703(19) Uani 1 1 d . . . . .
C10 C 0.20497(11) 0.68312(6) 0.42596(6) 0.0179(2) Uani 1 1 d . . . . .
C8 C 0.60773(11) 0.57545(6) 0.51251(7) 0.0205(2) Uani 1 1 d . . . . .
C9B C 0.40228(11) 0.41581(6) 0.98164(7) 0.0185(2) Uani 1 1 d . . . . .
C3 C 0.55679(12) 0.56106(5) 0.58581(7) 0.0192(2) Uani 1 1 d . . . . .
C2B C 0.47874(11) 0.40942(6) 1.12503(7) 0.0210(2) Uani 1 1 d . . . . .
C2 C 0.36115(11) 0.60906(6) 0.54095(7) 0.0186(2) Uani 1 1 d . . . . .
C10B C 0.28754(11) 0.44533(6) 1.00182(7) 0.0215(2) Uani 1 1 d . . . . .
C8B C 0.68674(12) 0.33495(7) 1.09088(7) 0.0252(2) Uani 1 1 d . . . . .
C7 C 0.74034(13) 0.55802(8) 0.50224(8) 0.0301(3) Uani 1 1 d . . . . .
H7 H 0.7758 0.5673 0.4534 0.036 Uiso 1 1 calc R . . . .
C3B C 0.66505(12) 0.35274(6) 1.16963(7) 0.0212(2) Uani 1 1 d . . . . .
C11B C 0.25745(12) 0.45540(7) 1.08720(7) 0.0249(2) Uani 1 1 d . . . . .
C3'B C 0.13203(13) 0.49232(7) 0.73807(8) 0.0289(3) Uani 1 1 d . . . . .
H3'B H 0.0855 0.5331 0.7474 0.035 Uiso 1 1 calc R . . . .
C1'B C 0.18306(14) 0.37897(8) 0.72455(8) 0.0315(3) Uani 1 1 d . . . . .
H1'B H 0.1765 0.3307 0.7234 0.038 Uiso 1 1 calc R . . . .
C2'B C 0.08209(13) 0.42510(7) 0.74302(8) 0.0290(3) Uani 1 1 d . . . . .
H2'B H -0.0037 0.4130 0.7563 0.035 Uiso 1 1 calc R . . . .
C4 C 0.63753(13) 0.52901(6) 0.64707(7) 0.0256(2) Uani 1 1 d . . . . .
H4 H 0.6033 0.5188 0.6961 0.031 Uiso 1 1 calc R . . . .
C11 C 0.17727(12) 0.68535(7) 0.51234(7) 0.0247(2) Uani 1 1 d . . . . .
C4'B C 0.26392(14) 0.48793(8) 0.71673(8) 0.0310(3) Uani 1 1 d . . . . .
H4'B H 0.3210 0.5253 0.7095 0.037 Uiso 1 1 calc R . . . .
C6 C 0.81762(13) 0.52759(8) 0.56310(9) 0.0326(3) Uani 1 1 d . . . . .
H6 H 0.9068 0.5165 0.5563 0.039 Uiso 1 1 calc R . . . .
C13B C 0.21033(14) 0.52767(8) 1.10197(9) 0.0326(3) Uani 1 1 d . . . . .
H13D H 0.2018 0.5339 1.1587 0.049 Uiso 1 1 calc GR . . . .
H13E H 0.1244 0.5351 1.0722 0.049 Uiso 1 1 calc GR . . . .
H13F H 0.2745 0.5604 1.0846 0.049 Uiso 1 1 calc GR . . . .
C5'B C 0.29546(14) 0.41792(8) 0.70806(7) 0.0314(3) Uani 1 1 d . . . . .
H5'B H 0.3771 0.4003 0.6938 0.038 Uiso 1 1 calc R . . . .
C5' C 0.25503(16) 0.72207(8) 0.13741(8) 0.0337(3) Uani 1 1 d . . . . .
H5' H 0.3256 0.6976 0.1176 0.040 Uiso 1 1 calc R . . . .
C5 C 0.76562(13) 0.51276(7) 0.63547(8) 0.0293(3) Uani 1 1 d . . . . .
H5 H 0.8199 0.4912 0.6767 0.035 Uiso 1 1 calc R . . . .
C4B C 0.75400(13) 0.32967(7) 1.23297(7) 0.0272(3) Uani 1 1 d . . . . .
H4B H 0.7406 0.3417 1.2860 0.033 Uiso 1 1 calc R . . . .
C3' C 0.13649(19) 0.80541(8) 0.19380(9) 0.0421(4) Uani 1 1 d . . . . .
H3' H 0.1138 0.8466 0.2188 0.050 Uiso 1 1 calc R . . . .
C5B C 0.85954(15) 0.28993(8) 1.21774(9) 0.0355(3) Uani 1 1 d . . . . .
H5B H 0.9190 0.2745 1.2605 0.043 Uiso 1 1 calc R . . . .
C2' C 0.04973(16) 0.75193(10) 0.17097(8) 0.0440(4) Uani 1 1 d . . . . .
H2' H -0.0421 0.7508 0.1775 0.053 Uiso 1 1 calc R . . . .
C1' C 0.12221(17) 0.70014(9) 0.13656(8) 0.0392(3) Uani 1 1 d . . . . .
H1' H 0.0879 0.6580 0.1164 0.047 Uiso 1 1 calc R . . . .
C12B C 0.15949(16) 0.40191(9) 1.11128(9) 0.0369(3) Uani 1 1 d . . . . .
H12D H 0.1958 0.3563 1.1041 0.055 Uiso 1 1 calc GR . . . .
H12E H 0.0759 0.4067 1.0781 0.055 Uiso 1 1 calc GR . . . .
H12F H 0.1439 0.4084 1.1670 0.055 Uiso 1 1 calc GR . . . .
C13 C 0.24124(18) 0.74908(8) 0.55091(8) 0.0376(3) Uani 1 1 d . . . . .
H13A H 0.2251 0.7503 0.6071 0.056 Uiso 1 1 calc GR . . . .
H13B H 0.2030 0.7897 0.5242 0.056 Uiso 1 1 calc GR . . . .
H13C H 0.3366 0.7480 0.5462 0.056 Uiso 1 1 calc GR . . . .
C4' C 0.26318(17) 0.78737(8) 0.17320(8) 0.0370(3) Uani 1 1 d . . . . .
H4' H 0.3407 0.8143 0.1818 0.044 Uiso 1 1 calc R . . . .
C7B C 0.79588(16) 0.29380(10) 1.07711(9) 0.0429(4) Uani 1 1 d . . . . .
H7B H 0.8108 0.2812 1.0245 0.051 Uiso 1 1 calc R . . . .
C6B C 0.88102(17) 0.27175(10) 1.13979(9) 0.0467(4) Uani 1 1 d . . . . .
H6B H 0.9546 0.2441 1.1302 0.056 Uiso 1 1 calc R . . . .
C12 C 0.03153(15) 0.68053(11) 0.52435(10) 0.0485(5) Uani 1 1 d . . . . .
H12A H -0.0067 0.6407 0.4960 0.073 Uiso 1 1 calc GR . . . .
H12B H -0.0137 0.7218 0.5038 0.073 Uiso 1 1 calc GR . . . .
H12C H 0.0208 0.6760 0.5810 0.073 Uiso 1 1 calc GR . . . .


_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 S1 2.1145(3) . ?
Co1 S2 2.1179(3) . ?
Co1 C5' 2.0553(13) . ?
Co1 C3' 2.0370(14) . ?
Co1 C2' 2.0422(14) . ?
Co1 C1' 2.0465(13) . ?
Co1 C4' 2.0413(14) . ?
Co1B S1B 2.1145(3) . ?
Co1B S2B 2.1206(3) . ?
Co1B C3'B 2.0545(13) . ?
Co1B C1'B 2.0517(14) . ?
Co1B C2'B 2.0543(13) . ?
Co1B C4'B 2.0484(13) . ?
Co1B C5'B 2.0526(13) . ?
S1 C9 1.7263(11) . ?
S2 C10 1.7086(11) . ?
S1B C9B 1.7282(11) . ?
S2B C10B 1.7133(12) . ?
O1 C2 1.3556(14) . ?
O1 C11 1.4650(14) . ?
O1B C2B 1.3479(15) . ?
O1B C11B 1.4620(15) . ?
N1 C1 1.3167(14) . ?
N1 C8 1.3750(15) . ?
N2 C3 1.3746(16) . ?
N2 C2 1.2948(15) . ?
N1B C1B 1.3153(15) . ?
N1B C8B 1.3731(15) . ?
N2B C2B 1.2957(15) . ?
N2B C3B 1.3707(16) . ?
C1B C9B 1.4545(15) . ?
C1B C2B 1.4458(16) . ?
C9 C1 1.4609(15) . ?
C9 C10 1.3734(15) . ?
C1 C2 1.4473(15) . ?
C10 C11 1.5155(16) . ?
C8 C3 1.4162(17) . ?
C8 C7 1.4166(17) . ?
C9B C10B 1.3729(16) . ?
C3 C4 1.4117(16) . ?
C10B C11B 1.5180(16) . ?
C8B C3B 1.4154(17) . ?
C8B C7B 1.4087(19) . ?
C7 H7 0.9500 . ?
C7 C6 1.3751(18) . ?
C3B C4B 1.4139(17) . ?
C11B C13B 1.5254(19) . ?
C11B C12B 1.528(2) . ?
C3'B H3'B 0.9500 . ?
C3'B C2'B 1.419(2) . ?
C3'B C4'B 1.4222(19) . ?
C1'B H1'B 0.9500 . ?
C1'B C2'B 1.425(2) . ?
C1'B C5'B 1.423(2) . ?
C2'B H2'B 0.9500 . ?
C4 H4 0.9500 . ?
C4 C5 1.3719(19) . ?
C11 C13 1.529(2) . ?
C11 C12 1.5165(19) . ?
C4'B H4'B 0.9500 . ?
C4'B C5'B 1.422(2) . ?
C6 H6 0.9500 . ?
C6 C5 1.409(2) . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 0.9800 . ?
C5'B H5'B 0.9500 . ?
C5' H5' 0.9500 . ?
C5' C1' 1.416(2) . ?
C5' C4' 1.417(2) . ?
C5 H5 0.9500 . ?
C4B H4B 0.9500 . ?
C4B C5B 1.370(2) . ?
C3' H3' 0.9500 . ?
C3' C2' 1.403(3) . ?
C3' C4' 1.410(2) . ?
C5B H5B 0.9500 . ?
C5B C6B 1.404(2) . ?
C2' H2' 0.9500 . ?
C2' C1' 1.412(2) . ?
C1' H1' 0.9500 . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C4' H4' 0.9500 . ?
C7B H7B 0.9500 . ?
C7B C6B 1.378(2) . ?
C6B H6B 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
S1 Co1 S2 92.298(12) . . ?
C5' Co1 S1 99.99(4) . . ?
C5' Co1 S2 167.71(4) . . ?
C3' Co1 S1 150.58(6) . . ?
C3' Co1 S2 101.13(4) . . ?
C3' Co1 C5' 68.10(6) . . ?
C3' Co1 C2' 40.24(8) . . ?
C3' Co1 C1' 67.96(7) . . ?
C3' Co1 C4' 40.44(7) . . ?
C2' Co1 S1 160.83(6) . . ?
C2' Co1 S2 100.14(4) . . ?
C2' Co1 C5' 67.89(6) . . ?
C2' Co1 C1' 40.41(7) . . ?
C1' Co1 S1 120.94(5) . . ?
C1' Co1 S2 131.17(5) . . ?
C1' Co1 C5' 40.39(7) . . ?
C4' Co1 S1 113.31(5) . . ?
C4' Co1 S2 133.62(5) . . ?
C4' Co1 C5' 40.49(6) . . ?
C4' Co1 C2' 67.74(7) . . ?
C4' Co1 C1' 67.90(7) . . ?
S1B Co1B S2B 91.973(13) . . ?
C3'B Co1B S1B 156.45(4) . . ?
C3'B Co1B S2B 101.72(4) . . ?
C1'B Co1B S1B 114.26(4) . . ?
C1'B Co1B S2B 135.70(4) . . ?
C1'B Co1B C3'B 68.18(6) . . ?
C1'B Co1B C2'B 40.61(6) . . ?
C1'B Co1B C5'B 40.58(6) . . ?
C2'B Co1B S1B 153.15(4) . . ?
C2'B Co1B S2B 103.46(4) . . ?
C2'B Co1B C3'B 40.42(6) . . ?
C4'B Co1B S1B 116.82(4) . . ?
C4'B Co1B S2B 131.84(5) . . ?
C4'B Co1B C3'B 40.56(5) . . ?
C4'B Co1B C1'B 68.24(6) . . ?
C4'B Co1B C2'B 68.15(5) . . ?
C4'B Co1B C5'B 40.58(6) . . ?
C5'B Co1B S1B 97.95(4) . . ?
C5'B Co1B S2B 169.85(4) . . ?
C5'B Co1B C3'B 68.22(6) . . ?
C5'B Co1B C2'B 68.24(6) . . ?
C9 S1 Co1 104.24(4) . . ?
C10 S2 Co1 104.81(4) . . ?
C9B S1B Co1B 104.53(4) . . ?
C10B S2B Co1B 105.30(4) . . ?
C2 O1 C11 117.36(9) . . ?
C2B O1B C11B 121.71(10) . . ?
C1 N1 C8 116.96(10) . . ?
C2 N2 C3 116.39(10) . . ?
C1B N1B C8B 117.01(10) . . ?
C2B N2B C3B 116.42(10) . . ?
N1B C1B C9B 121.32(10) . . ?
N1B C1B C2B 120.67(10) . . ?
C2B C1B C9B 117.99(10) . . ?
C1 C9 S1 122.02(8) . . ?
C10 C9 S1 119.26(8) . . ?
C10 C9 C1 118.69(10) . . ?
N1 C1 C9 121.94(10) . . ?
N1 C1 C2 120.62(10) . . ?
C2 C1 C9 117.43(10) . . ?
C9 C10 S2 119.20(8) . . ?
C9 C10 C11 120.79(10) . . ?
C11 C10 S2 119.58(8) . . ?
N1 C8 C3 121.37(10) . . ?
N1 C8 C7 119.51(11) . . ?
C3 C8 C7 119.12(11) . . ?
C1B C9B S1B 121.05(8) . . ?
C10B C9B S1B 119.56(9) . . ?
C10B C9B C1B 119.29(10) . . ?
N2 C3 C8 120.86(10) . . ?
N2 C3 C4 119.17(11) . . ?
C4 C3 C8 119.94(11) . . ?
O1B C2B C1B 120.98(10) . . ?
N2B C2B O1B 115.35(10) . . ?
N2B C2B C1B 123.60(11) . . ?
O1 C2 C1 120.15(10) . . ?
N2 C2 O1 116.07(10) . . ?
N2 C2 C1 123.71(11) . . ?
C9B C10B S2B 118.61(9) . . ?
C9B C10B C11B 122.75(10) . . ?
C11B C10B S2B 118.53(8) . . ?
N1B C8B C3B 121.30(11) . . ?
N1B C8B C7B 119.38(12) . . ?
C7B C8B C3B 119.30(11) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 C8 119.90(13) . . ?
C6 C7 H7 120.1 . . ?
N2B C3B C8B 120.98(11) . . ?
N2B C3B C4B 119.47(11) . . ?
C4B C3B C8B 119.54(11) . . ?
O1B C11B C10B 111.47(9) . . ?
O1B C11B C13B 103.35(11) . . ?
O1B C11B C12B 107.09(11) . . ?
C10B C11B C13B 111.76(11) . . ?
C10B C11B C12B 110.91(11) . . ?
C13B C11B C12B 111.95(11) . . ?
Co1B C3'B H3'B 126.3 . . ?
C2'B C3'B Co1B 69.78(7) . . ?
C2'B C3'B H3'B 126.0 . . ?
C2'B C3'B C4'B 107.99(12) . . ?
C4'B C3'B Co1B 69.49(7) . . ?
C4'B C3'B H3'B 126.0 . . ?
Co1B C1'B H1'B 126.0 . . ?
C2'B C1'B Co1B 69.79(8) . . ?
C2'B C1'B H1'B 126.0 . . ?
C5'B C1'B Co1B 69.74(8) . . ?
C5'B C1'B H1'B 126.0 . . ?
C5'B C1'B C2'B 107.96(13) . . ?
Co1B C2'B H2'B 126.2 . . ?
C3'B C2'B Co1B 69.80(7) . . ?
C3'B C2'B C1'B 108.04(12) . . ?
C3'B C2'B H2'B 126.0 . . ?
C1'B C2'B Co1B 69.60(7) . . ?
C1'B C2'B H2'B 126.0 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.66(12) . . ?
C5 C4 H4 120.2 . . ?
O1 C11 C10 109.75(9) . . ?
O1 C11 C13 108.27(10) . . ?
O1 C11 C12 104.01(11) . . ?
C10 C11 C13 109.11(11) . . ?
C10 C11 C12 113.36(11) . . ?
C12 C11 C13 112.13(13) . . ?
Co1B C4'B H4'B 125.8 . . ?
C3'B C4'B Co1B 69.95(7) . . ?
C3'B C4'B H4'B 125.9 . . ?
C5'B C4'B Co1B 69.87(8) . . ?
C5'B C4'B C3'B 108.15(12) . . ?
C5'B C4'B H4'B 125.9 . . ?
C7 C6 H6 119.7 . . ?
C7 C6 C5 120.57(13) . . ?
C5 C6 H6 119.7 . . ?
C11B C13B H13D 109.5 . . ?
C11B C13B H13E 109.5 . . ?
C11B C13B H13F 109.5 . . ?
H13D C13B H13E 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
Co1B C5'B H5'B 126.3 . . ?
C1'B C5'B Co1B 69.67(8) . . ?
C1'B C5'B H5'B 126.1 . . ?
C4'B C5'B Co1B 69.55(7) . . ?
C4'B C5'B C1'B 107.86(12) . . ?
C4'B C5'B H5'B 126.1 . . ?
Co1 C5' H5' 126.5 . . ?
C1' C5' Co1 69.47(8) . . ?
C1' C5' H5' 126.3 . . ?
C1' C5' C4' 107.36(13) . . ?
C4' C5' Co1 69.23(8) . . ?
C4' C5' H5' 126.3 . . ?
C4 C5 C6 120.80(12) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C3B C4B H4B 120.1 . . ?
C5B C4B C3B 119.85(12) . . ?
C5B C4B H4B 120.1 . . ?
Co1 C3' H3' 125.6 . . ?
C2' C3' Co1 70.08(8) . . ?
C2' C3' H3' 126.0 . . ?
C2' C3' C4' 108.01(14) . . ?
C4' C3' Co1 69.94(8) . . ?
C4' C3' H3' 126.0 . . ?
C4B C5B H5B 119.6 . . ?
C4B C5B C6B 120.86(12) . . ?
C6B C5B H5B 119.6 . . ?
Co1 C2' H2' 126.1 . . ?
C3' C2' Co1 69.68(9) . . ?
C3' C2' H2' 125.8 . . ?
C3' C2' C1' 108.32(14) . . ?
C1' C2' Co1 69.96(8) . . ?
C1' C2' H2' 125.8 . . ?
Co1 C1' H1' 125.8 . . ?
C5' C1' Co1 70.14(8) . . ?
C5' C1' H1' 126.0 . . ?
C2' C1' Co1 69.63(8) . . ?
C2' C1' C5' 108.02(15) . . ?
C2' C1' H1' 126.0 . . ?
C11B C12B H12D 109.5 . . ?
C11B C12B H12E 109.5 . . ?
C11B C12B H12F 109.5 . . ?
H12D C12B H12E 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
Co1 C4' H4' 125.8 . . ?
C5' C4' Co1 70.29(8) . . ?
C5' C4' H4' 125.9 . . ?
C3' C4' Co1 69.62(8) . . ?
C3' C4' C5' 108.29(15) . . ?
C3' C4' H4' 125.9 . . ?
C8B C7B H7B 119.9 . . ?
C6B C7B C8B 120.14(14) . . ?
C6B C7B H7B 119.9 . . ?
C5B C6B H6B 119.8 . . ?
C7B C6B C5B 120.31(14) . . ?
C7B C6B H6B 119.8 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Co1 S1 C9 C1 -172.99(8) . . . . ?
Co1 S1 C9 C10 4.81(10) . . . . ?
Co1 S2 C10 C9 0.39(10) . . . . ?
Co1 S2 C10 C11 172.87(9) . . . . ?
Co1 C5' C1' C2' 59.56(9) . . . . ?
Co1 C5' C4' C3' -59.46(9) . . . . ?
Co1 C3' C2' C1' -59.50(10) . . . . ?
Co1 C3' C4' C5' 59.88(10) . . . . ?
Co1 C2' C1' C5' -59.88(10) . . . . ?
Co1B S1B C9B C1B 174.57(9) . . . . ?
Co1B S1B C9B C10B -1.69(11) . . . . ?
Co1B S2B C10B C9B 0.54(11) . . . . ?
Co1B S2B C10B C11B -175.56(9) . . . . ?
Co1B C3'B C2'B C1'B -59.31(9) . . . . ?
Co1B C3'B C4'B C5'B 59.66(9) . . . . ?
Co1B C1'B C2'B C3'B 59.43(9) . . . . ?
Co1B C1'B C5'B C4'B -59.29(9) . . . . ?
Co1B C4'B C5'B C1'B 59.36(9) . . . . ?
S1 C9 C1 N1 12.94(16) . . . . ?
S1 C9 C1 C2 -167.64(8) . . . . ?
S1 C9 C10 S2 -3.59(14) . . . . ?
S1 C9 C10 C11 -175.98(9) . . . . ?
S2 C10 C11 O1 156.81(8) . . . . ?
S2 C10 C11 C13 -84.71(12) . . . . ?
S2 C10 C11 C12 41.01(16) . . . . ?
S1B C9B C10B S2B 0.79(15) . . . . ?
S1B C9B C10B C11B 176.72(10) . . . . ?
S2B C10B C11B O1B -167.49(9) . . . . ?
S2B C10B C11B C13B -52.39(14) . . . . ?
S2B C10B C11B C12B 73.29(14) . . . . ?
N1 C1 C2 O1 -179.60(11) . . . . ?
N1 C1 C2 N2 -2.98(18) . . . . ?
N1 C8 C3 N2 -2.85(17) . . . . ?
N1 C8 C3 C4 178.72(11) . . . . ?
N1 C8 C7 C6 -179.53(13) . . . . ?
N2 C3 C4 C5 -177.64(11) . . . . ?
N1B C1B C9B S1B -5.71(16) . . . . ?
N1B C1B C9B C10B 170.56(12) . . . . ?
N1B C1B C2B O1B 177.75(12) . . . . ?
N1B C1B C2B N2B 0.83(19) . . . . ?
N1B C8B C3B N2B 0.76(19) . . . . ?
N1B C8B C3B C4B 179.42(12) . . . . ?
N1B C8B C7B C6B -179.26(17) . . . . ?
N2B C3B C4B C5B 178.14(13) . . . . ?
C1B N1B C8B C3B -0.48(19) . . . . ?
C1B N1B C8B C7B 178.16(14) . . . . ?
C1B C9B C10B S2B -175.54(9) . . . . ?
C1B C9B C10B C11B 0.40(18) . . . . ?
C9 C1 C2 O1 0.98(16) . . . . ?
C9 C1 C2 N2 177.60(11) . . . . ?
C9 C10 C11 O1 -30.83(16) . . . . ?
C9 C10 C11 C13 87.65(14) . . . . ?
C9 C10 C11 C12 -146.63(13) . . . . ?
C1 N1 C8 C3 1.65(17) . . . . ?
C1 N1 C8 C7 -178.87(12) . . . . ?
C1 C9 C10 S2 174.27(8) . . . . ?
C1 C9 C10 C11 1.88(17) . . . . ?
C10 C9 C1 N1 -164.86(11) . . . . ?
C10 C9 C1 C2 14.55(16) . . . . ?
C8 N1 C1 C9 -179.54(10) . . . . ?
C8 N1 C1 C2 1.06(16) . . . . ?
C8 C3 C4 C5 0.81(18) . . . . ?
C8 C7 C6 C5 0.8(2) . . . . ?
C9B C1B C2B O1B -3.99(17) . . . . ?
C9B C1B C2B N2B 179.10(11) . . . . ?
C9B C10B C11B O1B 16.58(18) . . . . ?
C9B C10B C11B C13B 131.67(13) . . . . ?
C9B C10B C11B C12B -102.65(14) . . . . ?
C3 N2 C2 O1 178.52(10) . . . . ?
C3 N2 C2 C1 1.77(17) . . . . ?
C3 C8 C7 C6 0.0(2) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
C2B O1B C11B C10B -28.69(17) . . . . ?
C2B O1B C11B C13B -148.86(12) . . . . ?
C2B O1B C11B C12B 92.78(14) . . . . ?
C2B N2B C3B C8B -0.21(18) . . . . ?
C2B N2B C3B C4B -178.87(12) . . . . ?
C2B C1B C9B S1B 176.04(9) . . . . ?
C2B C1B C9B C10B -7.70(17) . . . . ?
C2 O1 C11 C10 46.32(14) . . . . ?
C2 O1 C11 C13 -72.68(13) . . . . ?
C2 O1 C11 C12 167.90(12) . . . . ?
C2 N2 C3 C8 1.02(16) . . . . ?
C2 N2 C3 C4 179.46(11) . . . . ?
C8B N1B C1B C9B -178.47(11) . . . . ?
C8B N1B C1B C2B -0.26(18) . . . . ?
C8B C3B C4B C5B -0.5(2) . . . . ?
C8B C7B C6B C5B 0.2(3) . . . . ?
C7 C8 C3 N2 177.67(11) . . . . ?
C7 C8 C3 C4 -0.76(17) . . . . ?
C7 C6 C5 C4 -0.7(2) . . . . ?
C3B N2B C2B O1B -177.62(11) . . . . ?
C3B N2B C2B C1B -0.55(18) . . . . ?
C3B C8B C7B C6B -0.6(3) . . . . ?
C3B C4B C5B C6B 0.1(2) . . . . ?
C11B O1B C2B N2B -159.18(12) . . . . ?
C11B O1B C2B C1B 23.66(18) . . . . ?
C3'B C4'B C5'B Co1B -59.71(9) . . . . ?
C3'B C4'B C5'B C1'B -0.35(15) . . . . ?
C2'B C3'B C4'B Co1B -59.37(9) . . . . ?
C2'B C3'B C4'B C5'B 0.29(14) . . . . ?
C2'B C1'B C5'B Co1B 59.56(9) . . . . ?
C2'B C1'B C5'B C4'B 0.27(15) . . . . ?
C11 O1 C2 N2 149.98(11) . . . . ?
C11 O1 C2 C1 -33.14(15) . . . . ?
C4'B C3'B C2'B Co1B 59.18(9) . . . . ?
C4'B C3'B C2'B C1'B -0.12(15) . . . . ?
C5'B C1'B C2'B Co1B -59.52(9) . . . . ?
C5'B C1'B C2'B C3'B -0.09(15) . . . . ?
C4B C5B C6B C7B 0.1(3) . . . . ?
C3' C2' C1' Co1 59.32(10) . . . . ?
C3' C2' C1' C5' -0.56(16) . . . . ?
C2' C3' C4' Co1 -60.00(10) . . . . ?
C2' C3' C4' C5' -0.11(16) . . . . ?
C1' C5' C4' Co1 59.24(9) . . . . ?
C1' C5' C4' C3' -0.23(15) . . . . ?
C4' C5' C1' Co1 -59.08(9) . . . . ?
C4' C5' C1' C2' 0.48(15) . . . . ?
C4' C3' C2' Co1 59.91(10) . . . . ?
C4' C3' C2' C1' 0.41(16) . . . . ?
C7B C8B C3B N2B -177.88(14) . . . . ?
C7B C8B C3B C4B 0.8(2) . . . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.138
_oxdiff_exptl_absorpt_empirical_full_min 0.706
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile / water'
