# 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 2014

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H32 Co2 N8 O8 S2, 2(C2 H3 N)'
_chemical_formula_sum            'C24 H38 Co2 N10 O8 S2'
_chemical_formula_weight         776.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_space_group_IT_number           14
_symmetry_space_group_name_H-M   'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   10.9888(11)
_cell_length_b                   8.6363(9)
_cell_length_c                   17.4813(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.688(4)
_cell_angle_gamma                90.00
_cell_volume                     1653.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9676
_cell_measurement_theta_min      2.633
_cell_measurement_theta_max      26.336

_exptl_crystal_description       prismatic
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.054
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             804
_exptl_absorpt_coefficient_mu    1.190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.925
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   
;
 SADABS (Sheldrick, 1996)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  APEXII-FR591
_diffrn_measurement_method       ω+φ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            49379
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0132
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         26.42
_reflns_number_total             3393
_reflns_number_gt                3155
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX (Bruker-AXS,2012)'
_computing_cell_refinement       'SAINT (Bruker-AXS,2012)'
_computing_data_reduction        'SAINT and XPREP (Bruker-AXS,2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0630P)²+0.8196P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         3393
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0242
_refine_ls_wR_factor_ref         0.1010
_refine_ls_wR_factor_gt          0.0761
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_restrained_S_all      1.179
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N5 N 0.0329(2) 0.2955(3) 0.22867(17) 0.0533(6) Uani 1 1 d . A 1
C11 C 0.0993(3) 0.3837(3) 0.20769(15) 0.0384(6) Uani 1 1 d . A 1
C12 C 0.1845(4) 0.4970(5) 0.1829(2) 0.0643(9) Uani 1 1 d . A 1
H12A H 0.1627 0.5997 0.2012 0.096 Uiso 1 1 calc R A 1
H12B H 0.1815 0.4975 0.1268 0.096 Uiso 1 1 calc R A 1
H12C H 0.2673 0.4705 0.2041 0.096 Uiso 1 1 calc R A 1
S1 S 0.63938(4) 0.17120(5) 0.48661(3) 0.01618(13) Uani 1 1 d . . .
O3 O 0.66291(13) 0.14410(16) 0.57069(8) 0.0209(3) Uani 1 1 d . . .
O2 O 0.53004(12) 0.27100(16) 0.46980(8) 0.0209(3) Uani 1 1 d . . .
O1 O 0.60139(12) 0.01341(16) 0.45395(8) 0.0196(3) Uani 1 1 d . . .
N2 N 0.39242(16) 0.1329(2) 0.18741(9) 0.0215(4) Uani 1 1 d . . .
O4 O 0.74587(13) 0.23316(18) 0.45354(9) 0.0242(3) Uani 1 1 d . . .
N4 N 0.09609(17) 0.3710(2) 0.42092(11) 0.0296(4) Uani 1 1 d . . .
N3 N 0.24184(16) 0.1963(2) 0.43199(10) 0.0221(4) Uani 1 1 d . . .
C10 C 0.3040(2) 0.4617(3) 0.39249(14) 0.0323(5) Uani 1 1 d . . .
H10A H 0.2591 0.5526 0.3718 0.048 Uiso 1 1 calc R . .
H10B H 0.3534 0.4191 0.3533 0.048 Uiso 1 1 calc R . .
H10C H 0.3575 0.4920 0.4376 0.048 Uiso 1 1 calc R . .
N1 N 0.42677(16) 0.1190(2) 0.31295(10) 0.0194(3) Uani 1 1 d . . .
C2 C 0.4980(2) 0.2157(3) 0.20668(12) 0.0260(5) Uani 1 1 d . . .
H12 H 0.5465 0.2686 0.1725 0.031 Uiso 1 1 calc R . .
C3 C 0.35177(18) 0.0762(2) 0.25286(12) 0.0186(4) Uani 1 1 d . . .
C5 C 0.23879(19) -0.0191(3) 0.25581(12) 0.0245(4) Uani 1 1 d . . .
H15A H 0.1671 0.0488 0.2520 0.037 Uiso 1 1 calc R . .
H15B H 0.2423 -0.0762 0.3044 0.037 Uiso 1 1 calc R . .
H15C H 0.2329 -0.0925 0.2129 0.037 Uiso 1 1 calc R . .
C8 C 0.21624(19) 0.3427(2) 0.41483(12) 0.0234(4) Uani 1 1 d . . .
C4 C 0.3359(2) 0.1128(3) 0.10923(12) 0.0299(5) Uani 1 1 d . . .
H18A H 0.2583 0.1692 0.1036 0.045 Uiso 1 1 calc R . .
H18B H 0.3210 0.0025 0.0993 0.045 Uiso 1 1 calc R . .
H18C H 0.3906 0.1533 0.0725 0.045 Uiso 1 1 calc R . .
C7 C 0.0431(2) 0.2340(3) 0.44273(15) 0.0360(6) Uani 1 1 d . . .
H19 H -0.0402 0.2183 0.4513 0.043 Uiso 1 1 calc R . .
C6 C 0.1332(2) 0.1272(3) 0.44941(14) 0.0300(5) Uani 1 1 d . . .
H20 H 0.1239 0.0220 0.4637 0.036 Uiso 1 1 calc R . .
C1 C 0.5185(2) 0.2067(3) 0.28390(12) 0.0246(4) Uani 1 1 d . . .
H21 H 0.5852 0.2529 0.3136 0.029 Uiso 1 1 calc R . .
C9 C 0.0325(3) 0.5170(4) 0.40341(17) 0.0482(7) Uani 1 1 d . . .
H23A H 0.0768 0.6018 0.4306 0.072 Uiso 1 1 calc R . .
H23B H -0.0505 0.5110 0.4199 0.072 Uiso 1 1 calc R . .
H23C H 0.0286 0.5360 0.3480 0.072 Uiso 1 1 calc R . .
Co1 Co 0.40687(2) 0.08821(3) 0.427560(14) 0.01652(11) 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
N5 C11 1.136(4) . ?
C11 C12 1.445(4) . ?
S1 O4 1.4493(14) . ?
S1 O2 1.4883(14) . ?
S1 O3 1.4899(14) . ?
S1 O1 1.5226(14) . ?
S1 Co1 2.7665(6) 3_656 ?
S1 Co1 2.7706(6) . ?
O3 Co1 2.1490(14) 3_656 ?
O2 Co1 2.1693(14) . ?
O1 Co1 2.2446(14) . ?
O1 Co1 2.2582(14) 3_656 ?
N2 C3 1.354(3) . ?
N2 C2 1.381(3) . ?
N2 C4 1.465(3) . ?
N4 C8 1.355(3) . ?
N4 C7 1.385(4) . ?
N4 C9 1.462(3) . ?
N3 C8 1.324(3) . ?
N3 C6 1.390(3) . ?
N3 Co1 2.0466(18) . ?
C10 C8 1.484(3) . ?
N1 C3 1.333(3) . ?
N1 C1 1.390(3) . ?
N1 Co1 2.0504(17) . ?
C2 C1 1.353(3) . ?
C3 C5 1.494(3) . ?
C7 C6 1.351(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 C11 C12 178.6(3) . . ?
O4 S1 O2 111.87(9) . . ?
O4 S1 O3 111.77(9) . . ?
O2 S1 O3 110.98(8) . . ?
O4 S1 O1 112.73(9) . . ?
O2 S1 O1 104.60(8) . . ?
O3 S1 O1 104.45(8) . . ?
O4 S1 Co1 134.87(6) . 3_656 ?
O2 S1 Co1 113.26(6) . 3_656 ?
O3 S1 Co1 50.40(6) . 3_656 ?
O1 S1 Co1 54.67(5) . 3_656 ?
O4 S1 Co1 134.18(7) . . ?
O2 S1 Co1 51.04(6) . . ?
O3 S1 Co1 114.04(6) . . ?
O1 S1 Co1 54.02(5) . . ?
Co1 S1 Co1 77.753(14) 3_656 . ?
S1 O3 Co1 97.32(7) . 3_656 ?
S1 O2 Co1 96.72(7) . . ?
S1 O1 Co1 92.68(7) . . ?
S1 O1 Co1 91.96(7) . 3_656 ?
Co1 O1 Co1 101.03(5) . 3_656 ?
C3 N2 C2 108.05(17) . . ?
C3 N2 C4 127.00(19) . . ?
C2 N2 C4 124.95(18) . . ?
C8 N4 C7 107.53(19) . . ?
C8 N4 C9 126.2(2) . . ?
C7 N4 C9 126.1(2) . . ?
C8 N3 C6 106.79(19) . . ?
C8 N3 Co1 126.82(15) . . ?
C6 N3 Co1 126.30(15) . . ?
C3 N1 C1 106.46(17) . . ?
C3 N1 Co1 128.71(14) . . ?
C1 N1 Co1 124.48(14) . . ?
C1 C2 N2 106.39(18) . . ?
N1 C3 N2 109.88(17) . . ?
N1 C3 C5 125.98(18) . . ?
N2 C3 C5 124.13(19) . . ?
N3 C8 N4 110.2(2) . . ?
N3 C8 C10 126.2(2) . . ?
N4 C8 C10 123.6(2) . . ?
C6 C7 N4 106.6(2) . . ?
C7 C6 N3 108.9(2) . . ?
C2 C1 N1 109.21(18) . . ?
N3 Co1 N1 98.25(7) . . ?
N3 Co1 O3 96.13(7) . 3_656 ?
N1 Co1 O3 101.64(6) . 3_656 ?
N3 Co1 O2 100.69(6) . . ?
N1 Co1 O2 97.17(6) . . ?
O3 Co1 O2 152.62(5) 3_656 . ?
N3 Co1 O1 162.82(6) . . ?
N1 Co1 O1 93.58(6) . . ?
O3 Co1 O1 93.63(5) 3_656 . ?
O2 Co1 O1 65.31(5) . . ?
N3 Co1 O1 92.31(6) . 3_656 ?
N1 Co1 O1 164.19(6) . 3_656 ?
O3 Co1 O1 65.35(5) 3_656 3_656 ?
O2 Co1 O1 92.37(5) . 3_656 ?
O1 Co1 O1 78.97(5) . 3_656 ?
N3 Co1 S1 98.40(5) . 3_656 ?
N1 Co1 S1 132.37(5) . 3_656 ?
O3 Co1 S1 32.29(4) 3_656 3_656 ?
O2 Co1 S1 122.81(4) . 3_656 ?
O1 Co1 S1 82.50(4) . 3_656 ?
O1 Co1 S1 33.37(4) 3_656 3_656 ?
N3 Co1 S1 131.37(5) . . ?
N1 Co1 S1 99.31(5) . . ?
O3 Co1 S1 123.74(4) 3_656 . ?
O2 Co1 S1 32.24(4) . . ?
O1 Co1 S1 33.30(4) . . ?
O1 Co1 S1 82.17(4) 3_656 . ?
S1 Co1 S1 102.247(15) 3_656 . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.42
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.651
_refine_diff_density_min         -1.046
_refine_diff_density_rms         0.314
_database_code_depnum_ccdc_archive 'CCDC 1019336'
