# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  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_test

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14.50 Cl2 Co N5.50 O'
_chemical_formula_weight         429.66

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.611(2)
_cell_length_b                   13.180(3)
_cell_length_c                   15.861(4)
_cell_angle_alpha                75.031(8)
_cell_angle_beta                 76.859(7)
_cell_angle_gamma                89.895(9)
_cell_volume                     1886.7(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2501
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      25.3

_exptl_crystal_description       Needle
_exptl_crystal_colour            Blue
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    1.208
_exptl_absorpt_correction_type   'Numerical analytical'
_exptl_absorpt_correction_T_min  0.7669
_exptl_absorpt_correction_T_max  0.8735
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14756
_diffrn_reflns_av_R_equivalents  0.2500
_diffrn_reflns_av_sigmaI/netI    0.2273
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         25.34
_reflns_number_total             6751
_reflns_number_gt                3432
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0680P)²+0.0000P] 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         6751
_refine_ls_number_parameters     463
_refine_ls_number_restraints     216
_refine_ls_R_factor_all          0.1139
_refine_ls_R_factor_gt           0.0843
_refine_ls_wR_factor_ref         0.2251
_refine_ls_wR_factor_gt          0.2078
_refine_ls_goodness_of_fit_ref   0.901
_refine_ls_restrained_S_all      0.896
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.01609(8) 0.46363(7) 0.26813(6) 0.0136(3) Uani 1 1 d . . .
Cl1 Cl 0.19139(16) 0.37183(14) 0.31539(13) 0.0230(4) Uani 1 1 d . . .
Cl2 Cl -0.09912(16) 0.39783(13) 0.18329(12) 0.0199(4) Uani 1 1 d . . .
O11 O 0.0791(4) 0.6086(4) 0.1996(3) 0.0176(10) Uani 1 1 d U . .
N11 N 0.0825(5) 0.7852(4) 0.1961(4) 0.0146(12) Uani 1 1 d U . .
N12 N 0.0962(5) 0.8341(4) 0.2581(4) 0.0136(11) Uani 1 1 d U . .
N13 N 0.1116(5) 0.7622(4) 0.3321(4) 0.0167(12) Uani 1 1 d U . .
N14 N 0.1109(5) 0.6680(4) 0.3216(4) 0.0167(12) Uani 1 1 d U . .
C11 C 0.0900(7) 0.6816(5) 0.2375(5) 0.0170(14) Uani 1 1 d U . .
C12 C 0.0961(7) 0.9454(5) 0.2448(5) 0.0155(14) Uani 1 1 d U . .
C13 C -0.0119(7) 0.9979(5) 0.2086(5) 0.0185(15) Uani 1 1 d U . .
H13A H -0.0836 0.9610 0.1937 0.022 Uiso 1 1 calc R . .
C14 C -0.0104(7) 1.1057(6) 0.1954(5) 0.0220(16) Uani 1 1 d U . .
H14B H -0.0807 1.1441 0.1692 0.026 Uiso 1 1 calc R . .
C15 C 0.0927(6) 1.1591(5) 0.2199(5) 0.0173(14) Uani 1 1 d U . .
H15A H 0.0896 1.2328 0.2131 0.021 Uiso 1 1 calc R . .
C16 C 0.1992(7) 1.1046(5) 0.2543(5) 0.0186(15) Uani 1 1 d U . .
H16A H 0.2700 1.1417 0.2699 0.022 Uiso 1 1 calc R . .
C17 C 0.2046(7) 0.9976(5) 0.2663(5) 0.0172(14) Uani 1 1 d U . .
H17A H 0.2793 0.9604 0.2885 0.021 Uiso 1 1 calc R . .
C18 C 0.1287(7) 0.7882(5) 0.4125(5) 0.0192(15) Uani 1 1 d U . .
C19 C 0.0210(7) 0.8364(6) 0.4590(5) 0.0231(16) Uani 1 1 d U . .
H19A H -0.0634 0.8541 0.4382 0.028 Uiso 1 1 calc R . .
C20 C 0.0398(8) 0.8581(7) 0.5375(6) 0.0341(19) Uani 1 1 d U . .
H20A H -0.0304 0.8941 0.5694 0.041 Uiso 1 1 calc R . .
C21 C 0.1624(8) 0.8269(6) 0.5690(6) 0.0331(19) Uani 1 1 d U . .
H21A H 0.1745 0.8397 0.6232 0.040 Uiso 1 1 calc R . .
C22 C 0.2645(8) 0.7776(6) 0.5209(6) 0.0292(18) Uani 1 1 d U . .
H22A H 0.3483 0.7581 0.5419 0.035 Uiso 1 1 calc R . .
C23 C 0.2493(7) 0.7552(6) 0.4426(5) 0.0233(16) Uani 1 1 d U . .
H23A H 0.3191 0.7187 0.4111 0.028 Uiso 1 1 calc R . .
N31 N -0.1269(6) 0.4836(5) 0.3759(4) 0.0185(13) Uani 1 1 d . . .
C31 C -0.2023(7) 0.5051(6) 0.4351(5) 0.0199(16) Uani 1 1 d . . .
C32 C -0.2955(7) 0.5332(6) 0.5094(5) 0.0263(17) Uani 1 1 d . . .
H32A H -0.3711 0.4772 0.5394 0.039 Uiso 1 1 calc R . .
H32B H -0.3388 0.5992 0.4872 0.039 Uiso 1 1 calc R . .
H32C H -0.2402 0.5422 0.5521 0.039 Uiso 1 1 calc R . .
Co2 Co 0.62962(8) 0.73123(7) 0.25889(6) 0.0148(3) Uani 1 1 d . . .
Cl3 Cl 0.72821(17) 0.79672(14) 0.35104(12) 0.0223(4) Uani 1 1 d . . .
Cl4 Cl 0.45865(17) 0.82455(15) 0.20572(13) 0.0237(4) Uani 1 1 d . . .
O41 O 0.5665(4) 0.5859(3) 0.3263(3) 0.0169(10) Uani 1 1 d U . .
N41 N 0.5595(5) 0.5155(4) 0.2051(4) 0.0141(12) Uani 1 1 d U . .
N42 N 0.5454(5) 0.4193(4) 0.2028(4) 0.0107(11) Uani 1 1 d U . .
N43 N 0.5362(5) 0.3530(4) 0.2839(4) 0.0128(11) Uani 1 1 d U . .
N44 N 0.5417(5) 0.4079(4) 0.3425(4) 0.0138(12) Uani 1 1 d U . .
C41 C 0.5570(6) 0.5086(5) 0.2929(5) 0.0150(14) Uani 1 1 d U . .
C42 C 0.5398(7) 0.3857(5) 0.1228(5) 0.0162(14) Uani 1 1 d U . .
C43 C 0.6516(7) 0.4230(5) 0.0484(5) 0.0208(15) Uani 1 1 d U . .
H43A H 0.7283 0.4676 0.0497 0.025 Uiso 1 1 calc R . .
C44 C 0.6464(7) 0.3921(6) -0.0285(5) 0.0242(16) Uani 1 1 d U . .
H44B H 0.7216 0.4154 -0.0808 0.029 Uiso 1 1 calc R . .
C45 C 0.5342(7) 0.3281(6) -0.0299(6) 0.0274(17) Uani 1 1 d U . .
H45A H 0.5331 0.3067 -0.0826 0.033 Uiso 1 1 calc R . .
C46 C 0.4231(7) 0.2952(6) 0.0455(5) 0.0220(16) Uani 1 1 d U . .
H46A H 0.3467 0.2499 0.0450 0.026 Uiso 1 1 calc R . .
C47 C 0.4229(7) 0.3280(5) 0.1217(5) 0.0177(15) Uani 1 1 d U . .
H47A H 0.3433 0.3108 0.1720 0.021 Uiso 1 1 calc R . .
C48 C 0.5208(6) 0.2409(5) 0.3091(5) 0.0148(14) Uani 1 1 d U . .
C49 C 0.5998(7) 0.1820(5) 0.2567(5) 0.0165(14) Uani 1 1 d U . .
H49A H 0.6633 0.2152 0.2009 0.020 Uiso 1 1 calc R . .
C50 C 0.5842(7) 0.0742(6) 0.2874(5) 0.0212(15) Uani 1 1 d U . .
H50A H 0.6376 0.0331 0.2518 0.025 Uiso 1 1 calc R . .
C51 C 0.4950(7) 0.0250(6) 0.3666(5) 0.0209(15) Uani 1 1 d U . .
H51A H 0.4871 -0.0496 0.3863 0.025 Uiso 1 1 calc R . .
C52 C 0.4153(7) 0.0832(5) 0.4191(5) 0.0203(15) Uani 1 1 d U . .
H52A H 0.3529 0.0482 0.4747 0.024 Uiso 1 1 calc R . .
C53 C 0.4256(7) 0.1933(5) 0.3911(5) 0.0162(14) Uani 1 1 d U . .
H53A H 0.3702 0.2341 0.4263 0.019 Uiso 1 1 calc R . .
N61 N 0.7798(6) 0.7183(5) 0.1511(4) 0.0212(14) Uani 1 1 d . . .
C61 C 0.8643(7) 0.6993(6) 0.0953(5) 0.0219(16) Uani 1 1 d . . .
C62 C 0.9689(7) 0.6721(6) 0.0239(5) 0.0270(18) Uani 1 1 d . . .
H62A H 0.9904 0.5982 0.0436 0.041 Uiso 1 1 calc R . .
H62B H 1.0569 0.7169 0.0095 0.041 Uiso 1 1 calc R . .
H62C H 0.9301 0.6828 -0.0296 0.041 Uiso 1 1 calc R . .
N1S N 0.2347(8) 0.8878(7) 0.9371(6) 0.055(2) Uani 1 1 d . . .
C1S C 0.2673(9) 0.9462(7) 0.9728(6) 0.036(2) Uani 1 1 d . . .
C2S C 0.3061(10) 1.0180(8) 1.0183(7) 0.050(3) Uani 1 1 d . . .
H2S1 H 0.2195 1.0448 1.0491 0.075 Uiso 1 1 calc R . .
H2S2 H 0.3668 1.0768 0.9747 0.075 Uiso 1 1 calc R . .
H2S3 H 0.3588 0.9817 1.0623 0.075 Uiso 1 1 calc R . .


_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 O11 1.957(5) . ?
Co1 N31 2.010(6) . ?
Co1 Cl1 2.2277(18) . ?
Co1 Cl2 2.2523(18) . ?
O11 C11 1.276(8) . ?
N11 N12 1.336(8) . ?
N11 C11 1.364(8) . ?
N12 N13 1.343(8) . ?
N12 C12 1.427(8) . ?
N13 N14 1.294(7) . ?
N13 C18 1.445(9) . ?
N14 C11 1.360(9) . ?
C12 C13 1.396(9) . ?
C12 C17 1.401(9) . ?
C13 C14 1.381(9) . ?
C13 H13A 0.9500 . ?
C14 C15 1.396(9) . ?
C14 H14B 0.9500 . ?
C15 C16 1.381(9) . ?
C15 H15A 0.9500 . ?
C16 C17 1.377(9) . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9500 . ?
C18 C23 1.380(9) . ?
C18 C19 1.383(9) . ?
C19 C20 1.397(11) . ?
C19 H19A 0.9500 . ?
C20 C21 1.403(11) . ?
C20 H20A 0.9500 . ?
C21 C22 1.372(10) . ?
C21 H21A 0.9500 . ?
C22 C23 1.386(11) . ?
C22 H22A 0.9500 . ?
C23 H23A 0.9500 . ?
N31 C31 1.147(9) . ?
C31 C32 1.439(10) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
Co2 O41 1.958(5) . ?
Co2 N61 2.015(6) . ?
Co2 Cl4 2.2385(18) . ?
Co2 Cl3 2.2501(19) . ?
O41 C41 1.276(8) . ?
N41 N42 1.287(7) . ?
N41 C41 1.365(9) . ?
N42 N43 1.340(7) . ?
N42 C42 1.459(8) . ?
N43 N44 1.326(7) . ?
N43 C48 1.426(8) . ?
N44 C41 1.345(8) . ?
C42 C47 1.363(9) . ?
C42 C43 1.383(10) . ?
C43 C44 1.393(10) . ?
C43 H43A 0.9500 . ?
C44 C45 1.378(10) . ?
C44 H44B 0.9500 . ?
C45 C46 1.382(10) . ?
C45 H45A 0.9500 . ?
C46 C47 1.385(10) . ?
C46 H46A 0.9500 . ?
C47 H47A 0.9500 . ?
C48 C49 1.383(9) . ?
C48 C53 1.400(10) . ?
C49 C50 1.373(9) . ?
C49 H49A 0.9500 . ?
C50 C51 1.352(10) . ?
C50 H50A 0.9500 . ?
C51 C52 1.380(10) . ?
C51 H51A 0.9500 . ?
C52 C53 1.400(9) . ?
C52 H52A 0.9500 . ?
C53 H53A 0.9500 . ?
N61 C61 1.137(9) . ?
C61 C62 1.454(10) . ?
C62 H62A 0.9800 . ?
C62 H62B 0.9800 . ?
C62 H62C 0.9800 . ?
N1S C1S 1.147(11) . ?
C1S C2S 1.425(12) . ?
C2S H2S1 0.9800 . ?
C2S H2S2 0.9800 . ?
C2S H2S3 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
O11 Co1 N31 102.4(2) . . ?
O11 Co1 Cl1 113.02(13) . . ?
N31 Co1 Cl1 108.39(17) . . ?
O11 Co1 Cl2 105.81(15) . . ?
N31 Co1 Cl2 109.18(16) . . ?
Cl1 Co1 Cl2 116.98(7) . . ?
C11 O11 Co1 122.3(5) . . ?
N12 N11 C11 103.5(5) . . ?
N11 N12 N13 109.1(5) . . ?
N11 N12 C12 124.1(6) . . ?
N13 N12 C12 126.9(6) . . ?
N14 N13 N12 111.5(6) . . ?
N14 N13 C18 124.9(6) . . ?
N12 N13 C18 123.6(5) . . ?
N13 N14 C11 104.2(6) . . ?
O11 C11 N14 125.8(6) . . ?
O11 C11 N11 122.5(6) . . ?
N14 C11 N11 111.6(6) . . ?
C13 C12 C17 122.8(6) . . ?
C13 C12 N12 117.8(6) . . ?
C17 C12 N12 119.3(6) . . ?
C14 C13 C12 117.3(6) . . ?
C14 C13 H13A 121.3 . . ?
C12 C13 H13A 121.3 . . ?
C13 C14 C15 121.0(6) . . ?
C13 C14 H14B 119.5 . . ?
C15 C14 H14B 119.5 . . ?
C16 C15 C14 119.9(6) . . ?
C16 C15 H15A 120.0 . . ?
C14 C15 H15A 120.0 . . ?
C17 C16 C15 121.2(6) . . ?
C17 C16 H16A 119.4 . . ?
C15 C16 H16A 119.4 . . ?
C16 C17 C12 117.6(6) . . ?
C16 C17 H17A 121.2 . . ?
C12 C17 H17A 121.2 . . ?
C23 C18 C19 123.2(7) . . ?
C23 C18 N13 117.0(6) . . ?
C19 C18 N13 119.6(6) . . ?
C18 C19 C20 118.1(7) . . ?
C18 C19 H19A 121.0 . . ?
C20 C19 H19A 121.0 . . ?
C19 C20 C21 119.9(8) . . ?
C19 C20 H20A 120.1 . . ?
C21 C20 H20A 120.1 . . ?
C22 C21 C20 119.4(8) . . ?
C22 C21 H21A 120.3 . . ?
C20 C21 H21A 120.3 . . ?
C21 C22 C23 122.1(7) . . ?
C21 C22 H22A 119.0 . . ?
C23 C22 H22A 119.0 . . ?
C18 C23 C22 117.3(7) . . ?
C18 C23 H23A 121.4 . . ?
C22 C23 H23A 121.4 . . ?
C31 N31 Co1 173.0(6) . . ?
N31 C31 C32 179.3(8) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O41 Co2 N61 104.6(2) . . ?
O41 Co2 Cl4 114.00(14) . . ?
N61 Co2 Cl4 106.47(18) . . ?
O41 Co2 Cl3 104.81(15) . . ?
N61 Co2 Cl3 110.79(16) . . ?
Cl4 Co2 Cl3 115.64(7) . . ?
C41 O41 Co2 126.1(5) . . ?
N42 N41 C41 104.2(5) . . ?
N41 N42 N43 111.1(5) . . ?
N41 N42 C42 125.0(6) . . ?
N43 N42 C42 124.0(5) . . ?
N44 N43 N42 109.3(5) . . ?
N44 N43 C48 122.3(6) . . ?
N42 N43 C48 128.4(5) . . ?
N43 N44 C41 104.0(6) . . ?
O41 C41 N44 122.6(7) . . ?
O41 C41 N41 125.9(6) . . ?
N44 C41 N41 111.5(6) . . ?
C47 C42 C43 123.4(7) . . ?
C47 C42 N42 120.0(6) . . ?
C43 C42 N42 116.5(6) . . ?
C42 C43 C44 116.8(6) . . ?
C42 C43 H43A 121.6 . . ?
C44 C43 H43A 121.6 . . ?
C45 C44 C43 121.2(7) . . ?
C45 C44 H44B 119.4 . . ?
C43 C44 H44B 119.4 . . ?
C44 C45 C46 119.8(8) . . ?
C44 C45 H45A 120.1 . . ?
C46 C45 H45A 120.1 . . ?
C45 C46 C47 120.2(7) . . ?
C45 C46 H46A 119.9 . . ?
C47 C46 H46A 119.9 . . ?
C42 C47 C46 118.3(7) . . ?
C42 C47 H47A 120.8 . . ?
C46 C47 H47A 120.8 . . ?
C49 C48 C53 121.7(6) . . ?
C49 C48 N43 121.6(6) . . ?
C53 C48 N43 116.7(6) . . ?
C50 C49 C48 118.4(7) . . ?
C50 C49 H49A 120.8 . . ?
C48 C49 H49A 120.8 . . ?
C51 C50 C49 122.0(7) . . ?
C51 C50 H50A 119.0 . . ?
C49 C50 H50A 119.0 . . ?
C50 C51 C52 120.0(7) . . ?
C50 C51 H51A 120.0 . . ?
C52 C51 H51A 120.0 . . ?
C51 C52 C53 120.7(7) . . ?
C51 C52 H52A 119.6 . . ?
C53 C52 H52A 119.6 . . ?
C52 C53 C48 117.3(6) . . ?
C52 C53 H53A 121.4 . . ?
C48 C53 H53A 121.4 . . ?
C61 N61 Co2 172.2(6) . . ?
N61 C61 C62 178.0(7) . . ?
C61 C62 H62A 109.5 . . ?
C61 C62 H62B 109.5 . . ?
H62A C62 H62B 109.5 . . ?
C61 C62 H62C 109.5 . . ?
H62A C62 H62C 109.5 . . ?
H62B C62 H62C 109.5 . . ?
N1S C1S C2S 179.1(11) . . ?
C1S C2S H2S1 109.5 . . ?
C1S C2S H2S2 109.5 . . ?
H2S1 C2S H2S2 109.5 . . ?
C1S C2S H2S3 109.5 . . ?
H2S1 C2S H2S3 109.5 . . ?
H2S2 C2S H2S3 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
N31 Co1 O11 C11 34.4(5) . . . . ?
Cl1 Co1 O11 C11 -82.0(5) . . . . ?
Cl2 Co1 O11 C11 148.7(4) . . . . ?
C11 N11 N12 N13 0.2(6) . . . . ?
C11 N11 N12 C12 179.4(5) . . . . ?
N11 N12 N13 N14 1.0(7) . . . . ?
C12 N12 N13 N14 -178.2(5) . . . . ?
N11 N12 N13 C18 -179.8(5) . . . . ?
C12 N12 N13 C18 1.0(9) . . . . ?
N12 N13 N14 C11 -1.7(7) . . . . ?
C18 N13 N14 C11 179.1(6) . . . . ?
Co1 O11 C11 N14 24.7(9) . . . . ?
Co1 O11 C11 N11 -155.7(5) . . . . ?
N13 N14 C11 O11 -178.5(6) . . . . ?
N13 N14 C11 N11 1.9(7) . . . . ?
N12 N11 C11 O11 179.1(6) . . . . ?
N12 N11 C11 N14 -1.3(7) . . . . ?
N11 N12 C12 C13 48.1(9) . . . . ?
N13 N12 C12 C13 -132.9(7) . . . . ?
N11 N12 C12 C17 -130.6(6) . . . . ?
N13 N12 C12 C17 48.5(9) . . . . ?
C17 C12 C13 C14 -1.0(11) . . . . ?
N12 C12 C13 C14 -179.5(6) . . . . ?
C12 C13 C14 C15 -1.9(11) . . . . ?
C13 C14 C15 C16 3.0(11) . . . . ?
C14 C15 C16 C17 -1.1(11) . . . . ?
C15 C16 C17 C12 -1.7(10) . . . . ?
C13 C12 C17 C16 2.8(11) . . . . ?
N12 C12 C17 C16 -178.7(6) . . . . ?
N14 N13 C18 C23 55.8(9) . . . . ?
N12 N13 C18 C23 -123.3(7) . . . . ?
N14 N13 C18 C19 -119.1(7) . . . . ?
N12 N13 C18 C19 61.8(9) . . . . ?
C23 C18 C19 C20 3.9(12) . . . . ?
N13 C18 C19 C20 178.6(7) . . . . ?
C18 C19 C20 C21 -2.9(12) . . . . ?
C19 C20 C21 C22 1.7(12) . . . . ?
C20 C21 C22 C23 -1.5(12) . . . . ?
C19 C18 C23 C22 -3.7(11) . . . . ?
N13 C18 C23 C22 -178.4(6) . . . . ?
C21 C22 C23 C18 2.4(12) . . . . ?
O11 Co1 N31 C31 -18(5) . . . . ?
Cl1 Co1 N31 C31 101(5) . . . . ?
Cl2 Co1 N31 C31 -130(4) . . . . ?
Co1 N31 C31 C32 -21(80) . . . . ?
N61 Co2 O41 C41 -34.1(5) . . . . ?
Cl4 Co2 O41 C41 81.8(5) . . . . ?
Cl3 Co2 O41 C41 -150.8(5) . . . . ?
C41 N41 N42 N43 -0.9(6) . . . . ?
C41 N41 N42 C42 179.1(5) . . . . ?
N41 N42 N43 N44 1.3(6) . . . . ?
C42 N42 N43 N44 -178.7(5) . . . . ?
N41 N42 N43 C48 -179.6(5) . . . . ?
C42 N42 N43 C48 0.4(8) . . . . ?
N42 N43 N44 C41 -1.1(6) . . . . ?
C48 N43 N44 C41 179.7(5) . . . . ?
Co2 O41 C41 N44 165.8(4) . . . . ?
Co2 O41 C41 N41 -14.7(9) . . . . ?
N43 N44 C41 O41 -179.9(5) . . . . ?
N43 N44 C41 N41 0.6(7) . . . . ?
N42 N41 C41 O41 -179.3(6) . . . . ?
N42 N41 C41 N44 0.2(7) . . . . ?
N41 N42 C42 C47 -121.0(7) . . . . ?
N43 N42 C42 C47 59.0(8) . . . . ?
N41 N42 C42 C43 53.7(8) . . . . ?
N43 N42 C42 C43 -126.3(6) . . . . ?
C47 C42 C43 C44 -4.9(10) . . . . ?
N42 C42 C43 C44 -179.5(6) . . . . ?
C42 C43 C44 C45 0.5(10) . . . . ?
C43 C44 C45 C46 1.1(11) . . . . ?
C44 C45 C46 C47 1.3(11) . . . . ?
C43 C42 C47 C46 7.4(10) . . . . ?
N42 C42 C47 C46 -178.3(6) . . . . ?
C45 C46 C47 C42 -5.4(10) . . . . ?
N44 N43 C48 C49 -137.3(6) . . . . ?
N42 N43 C48 C49 43.7(9) . . . . ?
N44 N43 C48 C53 40.6(8) . . . . ?
N42 N43 C48 C53 -138.5(6) . . . . ?
C53 C48 C49 C50 -0.7(9) . . . . ?
N43 C48 C49 C50 177.0(6) . . . . ?
C48 C49 C50 C51 -0.3(10) . . . . ?
C49 C50 C51 C52 0.6(11) . . . . ?
C50 C51 C52 C53 0.0(10) . . . . ?
C51 C52 C53 C48 -0.9(9) . . . . ?
C49 C48 C53 C52 1.3(9) . . . . ?
N43 C48 C53 C52 -176.6(5) . . . . ?
O41 Co2 N61 C61 -13(4) . . . . ?
Cl4 Co2 N61 C61 -134(4) . . . . ?
Cl3 Co2 N61 C61 99(4) . . . . ?
Co2 N61 C61 C62 55(26) . . . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        25.34
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         1.193
_refine_diff_density_min         -1.567
_refine_diff_density_rms         0.178
_database_code_depnum_ccdc_archive 'CCDC 999464'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  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.
#
data_shelxs

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14.50 Br2 Co N5.50 O'
_chemical_formula_weight         518.58

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'
Br Br -0.2901 2.4595 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.832(2)
_cell_length_b                   13.304(3)
_cell_length_c                   15.925(4)
_cell_angle_alpha                105.240(4)
_cell_angle_beta                 103.610(5)
_cell_angle_gamma                90.386(3)
_cell_volume                     1948.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3454
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      29.1

_exptl_crystal_description       Needle
_exptl_crystal_colour            Blue
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.768
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016
_exptl_absorpt_coefficient_mu    4.998
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_min  0.4200
_exptl_absorpt_correction_T_max  0.6094
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33380
_diffrn_reflns_av_R_equivalents  0.1200
_diffrn_reflns_av_sigmaI/netI    0.0790
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         29.14
_reflns_number_total             10000
_reflns_number_gt                8832
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1191P)²+9.4919P] 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         10000
_refine_ls_number_parameters     463
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0726
_refine_ls_wR_factor_ref         0.2127
_refine_ls_wR_factor_gt          0.2054
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
Co1 Co 0.02061(6) -0.02918(5) 0.72958(4) 0.01168(15) Uani 1 1 d . . .
Br1 Br -0.09220(5) -0.09884(4) 0.82034(3) 0.02059(14) Uani 1 1 d . . .
Br2 Br 0.19711(6) -0.12407(5) 0.68116(5) 0.03534(17) Uani 1 1 d . . .
O11 O 0.0799(4) 0.1161(3) 0.7971(2) 0.0164(6) Uani 1 1 d . . .
N11 N 0.0829(4) 0.2911(3) 0.7994(2) 0.0130(7) Uani 1 1 d . . .
N12 N 0.0976(4) 0.3381(3) 0.7384(2) 0.0115(6) Uani 1 1 d . . .
N13 N 0.1119(4) 0.2683(3) 0.6649(2) 0.0122(7) Uani 1 1 d . . .
N14 N 0.1101(4) 0.1727(3) 0.6747(3) 0.0151(7) Uani 1 1 d . . .
C11 C 0.0906(5) 0.1885(4) 0.7596(3) 0.0133(8) Uani 1 1 d . . .
C12 C 0.0991(4) 0.4483(3) 0.7516(3) 0.0117(7) Uani 1 1 d . . .
C13 C -0.0066(5) 0.5008(4) 0.7858(3) 0.0165(8) Uani 1 1 d . . .
H13A H -0.0786 0.4639 0.7987 0.020 Uiso 1 1 calc R . .
C14 C -0.0040(5) 0.6082(4) 0.8004(3) 0.0176(8) Uani 1 1 d . . .
H14B H -0.0733 0.6460 0.8254 0.021 Uiso 1 1 calc R . .
C15 C 0.1001(5) 0.6612(4) 0.7785(3) 0.0178(8) Uani 1 1 d . . .
H15A H 0.0997 0.7346 0.7867 0.021 Uiso 1 1 calc R . .
C16 C 0.2044(5) 0.6065(4) 0.7448(3) 0.0178(8) Uani 1 1 d . . .
H16A H 0.2758 0.6431 0.7309 0.021 Uiso 1 1 calc R . .
C17 C 0.2057(5) 0.4993(4) 0.7311(3) 0.0155(8) Uani 1 1 d . . .
H17A H 0.2773 0.4619 0.7085 0.019 Uiso 1 1 calc R . .
C18 C 0.1307(5) 0.2907(4) 0.5836(3) 0.0152(8) Uani 1 1 d . . .
C19 C 0.0276(6) 0.3405(4) 0.5377(3) 0.0241(10) Uani 1 1 d . . .
H19A H -0.0539 0.3602 0.5585 0.029 Uiso 1 1 calc R . .
C20 C 0.0484(7) 0.3604(5) 0.4598(3) 0.0298(12) Uani 1 1 d . . .
H20A H -0.0187 0.3958 0.4269 0.036 Uiso 1 1 calc R . .
C21 C 0.1683(7) 0.3282(5) 0.4299(4) 0.0337(13) Uani 1 1 d . . .
H21A H 0.1809 0.3406 0.3761 0.040 Uiso 1 1 calc R . .
C22 C 0.2671(6) 0.2790(5) 0.4773(4) 0.0293(12) Uani 1 1 d . . .
H22A H 0.3479 0.2579 0.4561 0.035 Uiso 1 1 calc R . .
C23 C 0.2508(5) 0.2594(4) 0.5566(3) 0.0223(10) Uani 1 1 d . . .
H23A H 0.3195 0.2260 0.5904 0.027 Uiso 1 1 calc R . .
N31 N -0.1241(4) -0.0153(3) 0.6220(3) 0.0185(8) Uani 1 1 d . . .
C31 C -0.2036(5) 0.0003(4) 0.5630(3) 0.0183(9) Uani 1 1 d . . .
C32 C -0.3032(6) 0.0202(5) 0.4879(3) 0.0279(11) Uani 1 1 d . . .
H32A H -0.2555 0.0239 0.4412 0.042 Uiso 1 1 calc R . .
H32B H -0.3440 0.0867 0.5078 0.042 Uiso 1 1 calc R . .
H32C H -0.3778 -0.0363 0.4637 0.042 Uiso 1 1 calc R . .
Co2 Co 0.63387(6) 1.22846(5) 0.73959(4) 0.01181(15) Uani 1 1 d . . .
Br3 Br 0.72605(5) 1.29592(4) 0.63868(3) 0.02175(14) Uani 1 1 d . . .
Br4 Br 0.45968(6) 1.32462(5) 0.79517(4) 0.02733(15) Uani 1 1 d . . .
O41 O 0.5739(3) 1.0835(2) 0.6742(2) 0.0145(6) Uani 1 1 d . . .
N41 N 0.5483(4) 0.9059(3) 0.6587(2) 0.0118(6) Uani 1 1 d . . .
N42 N 0.5409(4) 0.8541(3) 0.7176(2) 0.0095(6) Uani 1 1 d . . .
N43 N 0.5512(4) 0.9195(3) 0.7989(2) 0.0106(6) Uani 1 1 d . . .
N44 N 0.5676(4) 1.0164(3) 0.7960(2) 0.0132(7) Uani 1 1 d . . .
C41 C 0.5642(4) 1.0080(3) 0.7088(3) 0.0117(7) Uani 1 1 d . . .
C42 C 0.5245(4) 0.7417(3) 0.6923(3) 0.0121(7) Uani 1 1 d . . .
C43 C 0.4314(5) 0.6935(4) 0.6108(3) 0.0151(8) Uani 1 1 d . . .
H43A H 0.3783 0.7338 0.5754 0.018 Uiso 1 1 calc R . .
C44 C 0.4179(5) 0.5863(4) 0.5824(3) 0.0190(9) Uani 1 1 d . . .
H44B H 0.3551 0.5522 0.5266 0.023 Uiso 1 1 calc R . .
C45 C 0.4950(5) 0.5269(4) 0.6343(3) 0.0196(9) Uani 1 1 d . . .
H45A H 0.4849 0.4528 0.6141 0.024 Uiso 1 1 calc R . .
C46 C 0.5872(5) 0.5770(4) 0.7163(3) 0.0188(9) Uani 1 1 d . . .
H46A H 0.6393 0.5365 0.7519 0.023 Uiso 1 1 calc R . .
C47 C 0.6040(5) 0.6846(4) 0.7465(3) 0.0148(8) Uani 1 1 d . . .
H47A H 0.6671 0.7188 0.8022 0.018 Uiso 1 1 calc R . .
C48 C 0.5468(5) 0.8905(3) 0.8796(3) 0.0140(8) Uani 1 1 d . . .
C49 C 0.4326(6) 0.8282(4) 0.8784(3) 0.0212(9) Uani 1 1 d . . .
H49A H 0.3573 0.8061 0.8263 0.025 Uiso 1 1 calc R . .
C50 C 0.4319(7) 0.7991(4) 0.9559(4) 0.0281(12) Uani 1 1 d . . .
H50A H 0.3558 0.7554 0.9569 0.034 Uiso 1 1 calc R . .
C51 C 0.5420(7) 0.8336(5) 1.0322(3) 0.0299(12) Uani 1 1 d . . .
H51A H 0.5418 0.8125 1.0847 0.036 Uiso 1 1 calc R . .
C52 C 0.6520(6) 0.8988(5) 1.0314(3) 0.0272(11) Uani 1 1 d . . .
H52A H 0.7256 0.9240 1.0841 0.033 Uiso 1 1 calc R . .
C53 C 0.6553(5) 0.9276(4) 0.9543(3) 0.0203(9) Uani 1 1 d . . .
H53A H 0.7307 0.9719 0.9532 0.024 Uiso 1 1 calc R . .
N61 N 0.7860(4) 1.2211(3) 0.8468(3) 0.0175(7) Uani 1 1 d . . .
C61 C 0.8706(5) 1.2049(4) 0.9037(3) 0.0172(8) Uani 1 1 d . . .
C62 C 0.9761(6) 1.1833(5) 0.9758(3) 0.0251(10) Uani 1 1 d . . .
H62A H 0.9367 1.1883 1.0277 0.038 Uiso 1 1 calc R . .
H62B H 1.0570 1.2342 0.9927 0.038 Uiso 1 1 calc R . .
H62C H 1.0059 1.1127 0.9557 0.038 Uiso 1 1 calc R . .
N1S N 0.2252(8) 0.3957(7) 0.0673(4) 0.059(2) Uani 1 1 d . . .
C1S C 0.2575(7) 0.4489(6) 0.0284(4) 0.0383(14) Uani 1 1 d . . .
C2S C 0.3005(8) 0.5180(6) -0.0192(4) 0.0420(15) Uani 1 1 d . . .
H2S1 H 0.3762 0.5682 0.0215 0.063 Uiso 1 1 calc R . .
H2S2 H 0.2204 0.5556 -0.0412 0.063 Uiso 1 1 calc R . .
H2S3 H 0.3338 0.4768 -0.0702 0.063 Uiso 1 1 calc R . .


_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 O11 1.957(3) . ?
Co1 N31 2.004(4) . ?
Co1 Br2 2.3125(9) . ?
Co1 Br1 2.3713(8) . ?
O11 C11 1.276(5) . ?
N11 N12 1.319(5) . ?
N11 C11 1.357(6) . ?
N12 N13 1.327(5) . ?
N12 C12 1.425(5) . ?
N13 N14 1.322(5) . ?
N13 C18 1.453(5) . ?
N14 C11 1.372(5) . ?
C12 C17 1.391(6) . ?
C12 C13 1.393(6) . ?
C13 C14 1.385(7) . ?
C13 H13A 0.9500 . ?
C14 C15 1.398(6) . ?
C14 H14B 0.9500 . ?
C15 C16 1.391(6) . ?
C15 H15A 0.9500 . ?
C16 C17 1.385(6) . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9500 . ?
C18 C23 1.380(6) . ?
C18 C19 1.384(7) . ?
C19 C20 1.395(6) . ?
C19 H19A 0.9500 . ?
C20 C21 1.401(9) . ?
C20 H20A 0.9500 . ?
C21 C22 1.366(9) . ?
C21 H21A 0.9500 . ?
C22 C23 1.399(7) . ?
C22 H22A 0.9500 . ?
C23 H23A 0.9500 . ?
N31 C31 1.139(6) . ?
C31 C32 1.442(7) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
Co2 O41 1.948(3) . ?
Co2 N61 2.012(4) . ?
Co2 Br4 2.3455(8) . ?
Co2 Br3 2.3753(8) . ?
O41 C41 1.279(5) . ?
N41 N42 1.316(5) . ?
N41 C41 1.369(6) . ?
N42 N43 1.338(5) . ?
N42 C42 1.440(5) . ?
N43 N44 1.312(5) . ?
N43 C48 1.445(5) . ?
N44 C41 1.356(5) . ?
C42 C43 1.389(6) . ?
C42 C47 1.403(6) . ?
C43 C44 1.374(7) . ?
C43 H43A 0.9500 . ?
C44 C45 1.392(7) . ?
C44 H44B 0.9500 . ?
C45 C46 1.397(7) . ?
C45 H45A 0.9500 . ?
C46 C47 1.380(6) . ?
C46 H46A 0.9500 . ?
C47 H47A 0.9500 . ?
C48 C53 1.372(7) . ?
C48 C49 1.385(7) . ?
C49 C50 1.389(6) . ?
C49 H49A 0.9500 . ?
C50 C51 1.392(9) . ?
C50 H50A 0.9500 . ?
C51 C52 1.387(9) . ?
C51 H51A 0.9500 . ?
C52 C53 1.386(6) . ?
C52 H52A 0.9500 . ?
C53 H53A 0.9500 . ?
N61 C61 1.145(6) . ?
C61 C62 1.447(6) . ?
C62 H62A 0.9800 . ?
C62 H62B 0.9800 . ?
C62 H62C 0.9800 . ?
N1S C1S 1.142(10) . ?
C1S C2S 1.453(10) . ?
C2S H2S1 0.9800 . ?
C2S H2S2 0.9800 . ?
C2S H2S3 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
O11 Co1 N31 103.04(16) . . ?
O11 Co1 Br2 114.27(10) . . ?
N31 Co1 Br2 108.68(12) . . ?
O11 Co1 Br1 105.69(10) . . ?
N31 Co1 Br1 108.75(12) . . ?
Br2 Co1 Br1 115.58(3) . . ?
C11 O11 Co1 123.1(3) . . ?
N12 N11 C11 103.9(3) . . ?
N11 N12 N13 110.3(3) . . ?
N11 N12 C12 123.9(3) . . ?
N13 N12 C12 125.8(3) . . ?
N14 N13 N12 111.1(3) . . ?
N14 N13 C18 122.7(4) . . ?
N12 N13 C18 126.1(4) . . ?
N13 N14 C11 102.8(4) . . ?
O11 C11 N11 123.5(4) . . ?
O11 C11 N14 124.6(4) . . ?
N11 C11 N14 111.9(4) . . ?
C17 C12 C13 122.6(4) . . ?
C17 C12 N12 119.3(4) . . ?
C13 C12 N12 118.1(4) . . ?
C14 C13 C12 118.3(4) . . ?
C14 C13 H13A 120.8 . . ?
C12 C13 H13A 120.8 . . ?
C13 C14 C15 120.3(4) . . ?
C13 C14 H14B 119.9 . . ?
C15 C14 H14B 119.9 . . ?
C16 C15 C14 119.9(4) . . ?
C16 C15 H15A 120.1 . . ?
C14 C15 H15A 120.1 . . ?
C17 C16 C15 120.9(4) . . ?
C17 C16 H16A 119.5 . . ?
C15 C16 H16A 119.5 . . ?
C16 C17 C12 117.9(4) . . ?
C16 C17 H17A 121.0 . . ?
C12 C17 H17A 121.0 . . ?
C23 C18 C19 124.1(4) . . ?
C23 C18 N13 117.3(4) . . ?
C19 C18 N13 118.6(4) . . ?
C18 C19 C20 117.2(5) . . ?
C18 C19 H19A 121.4 . . ?
C20 C19 H19A 121.4 . . ?
C19 C20 C21 120.0(5) . . ?
C19 C20 H20A 120.0 . . ?
C21 C20 H20A 120.0 . . ?
C22 C21 C20 120.7(5) . . ?
C22 C21 H21A 119.6 . . ?
C20 C21 H21A 119.6 . . ?
C21 C22 C23 120.8(5) . . ?
C21 C22 H22A 119.6 . . ?
C23 C22 H22A 119.6 . . ?
C18 C23 C22 117.2(5) . . ?
C18 C23 H23A 121.4 . . ?
C22 C23 H23A 121.4 . . ?
C31 N31 Co1 174.9(4) . . ?
N31 C31 C32 179.5(5) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O41 Co2 N61 104.94(16) . . ?
O41 Co2 Br4 114.50(10) . . ?
N61 Co2 Br4 106.81(12) . . ?
O41 Co2 Br3 104.36(9) . . ?
N61 Co2 Br3 111.17(12) . . ?
Br4 Co2 Br3 114.71(3) . . ?
C41 O41 Co2 126.2(3) . . ?
N42 N41 C41 103.1(3) . . ?
N41 N42 N43 110.9(3) . . ?
N41 N42 C42 121.4(3) . . ?
N43 N42 C42 127.7(3) . . ?
N44 N43 N42 110.0(3) . . ?
N44 N43 C48 123.7(3) . . ?
N42 N43 C48 126.3(4) . . ?
N43 N44 C41 104.2(3) . . ?
O41 C41 N44 126.3(4) . . ?
O41 C41 N41 122.0(4) . . ?
N44 C41 N41 111.7(4) . . ?
C43 C42 C47 122.2(4) . . ?
C43 C42 N42 116.9(4) . . ?
C47 C42 N42 120.8(4) . . ?
C44 C43 C42 118.6(4) . . ?
C44 C43 H43A 120.7 . . ?
C42 C43 H43A 120.7 . . ?
C43 C44 C45 120.9(5) . . ?
C43 C44 H44B 119.6 . . ?
C45 C44 H44B 119.6 . . ?
C44 C45 C46 119.6(4) . . ?
C44 C45 H45A 120.2 . . ?
C46 C45 H45A 120.2 . . ?
C47 C46 C45 121.0(4) . . ?
C47 C46 H46A 119.5 . . ?
C45 C46 H46A 119.5 . . ?
C46 C47 C42 117.7(4) . . ?
C46 C47 H47A 121.1 . . ?
C42 C47 H47A 121.1 . . ?
C53 C48 C49 123.1(4) . . ?
C53 C48 N43 118.3(4) . . ?
C49 C48 N43 118.6(4) . . ?
C48 C49 C50 117.7(5) . . ?
C48 C49 H49A 121.1 . . ?
C50 C49 H49A 121.1 . . ?
C49 C50 C51 120.4(5) . . ?
C49 C50 H50A 119.8 . . ?
C51 C50 H50A 119.8 . . ?
C52 C51 C50 119.9(4) . . ?
C52 C51 H51A 120.1 . . ?
C50 C51 H51A 120.1 . . ?
C53 C52 C51 120.5(5) . . ?
C53 C52 H52A 119.8 . . ?
C51 C52 H52A 119.8 . . ?
C48 C53 C52 118.3(5) . . ?
C48 C53 H53A 120.9 . . ?
C52 C53 H53A 120.8 . . ?
C61 N61 Co2 172.2(4) . . ?
N61 C61 C62 179.1(5) . . ?
C61 C62 H62A 109.5 . . ?
C61 C62 H62B 109.5 . . ?
H62A C62 H62B 109.5 . . ?
C61 C62 H62C 109.5 . . ?
H62A C62 H62C 109.5 . . ?
H62B C62 H62C 109.5 . . ?
N1S C1S C2S 178.8(8) . . ?
C1S C2S H2S1 109.5 . . ?
C1S C2S H2S2 109.5 . . ?
H2S1 C2S H2S2 109.5 . . ?
C1S C2S H2S3 109.5 . . ?
H2S1 C2S H2S3 109.5 . . ?
H2S2 C2S H2S3 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
N31 Co1 O11 C11 -36.3(4) . . . . ?
Br2 Co1 O11 C11 81.4(3) . . . . ?
Br1 Co1 O11 C11 -150.4(3) . . . . ?
C11 N11 N12 N13 0.7(5) . . . . ?
C11 N11 N12 C12 -178.7(4) . . . . ?
N11 N12 N13 N14 -1.3(5) . . . . ?
C12 N12 N13 N14 178.1(4) . . . . ?
N11 N12 N13 C18 -179.8(4) . . . . ?
C12 N12 N13 C18 -0.4(7) . . . . ?
N12 N13 N14 C11 1.2(5) . . . . ?
C18 N13 N14 C11 179.9(4) . . . . ?
Co1 O11 C11 N11 156.2(3) . . . . ?
Co1 O11 C11 N14 -23.4(6) . . . . ?
N12 N11 C11 O11 -179.5(4) . . . . ?
N12 N11 C11 N14 0.1(5) . . . . ?
N13 N14 C11 O11 178.8(4) . . . . ?
N13 N14 C11 N11 -0.8(5) . . . . ?
N11 N12 C12 C17 130.6(4) . . . . ?
N13 N12 C12 C17 -48.7(6) . . . . ?
N11 N12 C12 C13 -48.6(6) . . . . ?
N13 N12 C12 C13 132.1(4) . . . . ?
C17 C12 C13 C14 -0.5(7) . . . . ?
N12 C12 C13 C14 178.7(4) . . . . ?
C12 C13 C14 C15 1.9(7) . . . . ?
C13 C14 C15 C16 -2.2(7) . . . . ?
C14 C15 C16 C17 1.0(7) . . . . ?
C15 C16 C17 C12 0.5(7) . . . . ?
C13 C12 C17 C16 -0.7(7) . . . . ?
N12 C12 C17 C16 -179.9(4) . . . . ?
N14 N13 C18 C23 -57.5(6) . . . . ?
N12 N13 C18 C23 120.9(5) . . . . ?
N14 N13 C18 C19 121.8(5) . . . . ?
N12 N13 C18 C19 -59.8(6) . . . . ?
C23 C18 C19 C20 -0.5(8) . . . . ?
N13 C18 C19 C20 -179.7(5) . . . . ?
C18 C19 C20 C21 1.4(9) . . . . ?
C19 C20 C21 C22 -1.3(9) . . . . ?
C20 C21 C22 C23 0.2(9) . . . . ?
C19 C18 C23 C22 -0.6(8) . . . . ?
N13 C18 C23 C22 178.6(4) . . . . ?
C21 C22 C23 C18 0.7(8) . . . . ?
O11 Co1 N31 C31 7(4) . . . . ?
Br2 Co1 N31 C31 -114(4) . . . . ?
Br1 Co1 N31 C31 119(4) . . . . ?
Co1 N31 C31 C32 70(71) . . . . ?
N61 Co2 O41 C41 36.7(4) . . . . ?
Br4 Co2 O41 C41 -80.1(4) . . . . ?
Br3 Co2 O41 C41 153.7(3) . . . . ?
C41 N41 N42 N43 0.2(4) . . . . ?
C41 N41 N42 C42 -179.6(3) . . . . ?
N41 N42 N43 N44 -0.9(5) . . . . ?
C42 N42 N43 N44 178.9(4) . . . . ?
N41 N42 N43 C48 179.7(4) . . . . ?
C42 N42 N43 C48 -0.5(6) . . . . ?
N42 N43 N44 C41 1.2(4) . . . . ?
C48 N43 N44 C41 -179.4(4) . . . . ?
Co2 O41 C41 N44 13.4(6) . . . . ?
Co2 O41 C41 N41 -166.8(3) . . . . ?
N43 N44 C41 O41 178.7(4) . . . . ?
N43 N44 C41 N41 -1.1(5) . . . . ?
N42 N41 C41 O41 -179.2(4) . . . . ?
N42 N41 C41 N44 0.6(5) . . . . ?
N41 N42 C42 C43 -41.5(5) . . . . ?
N43 N42 C42 C43 138.8(4) . . . . ?
N41 N42 C42 C47 136.0(4) . . . . ?
N43 N42 C42 C47 -43.7(6) . . . . ?
C47 C42 C43 C44 -0.4(6) . . . . ?
N42 C42 C43 C44 177.0(4) . . . . ?
C42 C43 C44 C45 0.4(6) . . . . ?
C43 C44 C45 C46 0.0(7) . . . . ?
C44 C45 C46 C47 -0.4(7) . . . . ?
C45 C46 C47 C42 0.4(6) . . . . ?
C43 C42 C47 C46 0.0(6) . . . . ?
N42 C42 C47 C46 -177.3(4) . . . . ?
N44 N43 C48 C53 -53.4(6) . . . . ?
N42 N43 C48 C53 125.8(5) . . . . ?
N44 N43 C48 C49 125.5(5) . . . . ?
N42 N43 C48 C49 -55.2(6) . . . . ?
C53 C48 C49 C50 -2.6(7) . . . . ?
N43 C48 C49 C50 178.5(4) . . . . ?
C48 C49 C50 C51 1.1(8) . . . . ?
C49 C50 C51 C52 1.1(8) . . . . ?
C50 C51 C52 C53 -1.9(8) . . . . ?
C49 C48 C53 C52 1.8(7) . . . . ?
N43 C48 C53 C52 -179.3(4) . . . . ?
C51 C52 C53 C48 0.5(7) . . . . ?
O41 Co2 N61 C61 4(3) . . . . ?
Br4 Co2 N61 C61 126(3) . . . . ?
Br3 Co2 N61 C61 -109(3) . . . . ?
Co2 N61 C61 C62 -54(40) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C15 H15A Br1 0.95 2.94 3.710(5) 138.6 1_565
C53 H53A Br1 0.95 3.02 3.599(5) 120.9 1_665
C62 H62C Br1 0.98 3.05 3.868(6) 142.0 1_665
C62 H62A Br1 0.98 3.07 3.647(5) 119.1 2_667
C32 H32A Br2 0.98 2.79 3.675(6) 150.7 2_556
C43 H43A Br2 0.95 3.06 3.509(4) 110.6 1_565
C49 H49A Br2 0.95 2.85 3.644(5) 141.7 1_565
C19 H19A Br3 0.95 2.98 3.801(5) 145.1 1_445
C32 H32B Br3 0.98 2.97 3.786(6) 141.5 1_445
C17 H17A Br4 0.95 2.94 3.578(5) 125.4 1_545
C51 H51A Br4 0.95 2.97 3.879(5) 160.3 2_677
C2S H2S1 Br4 0.98 2.95 3.837(7) 150.6 2_676
C2S H2S3 Br4 0.98 3.04 4.005(8) 169.4 1_544

_diffrn_measured_fraction_theta_max 0.950
_diffrn_reflns_theta_full        29.14
_diffrn_measured_fraction_theta_full 0.950
_refine_diff_density_max         2.428
_refine_diff_density_min         -3.123
_refine_diff_density_rms         0.227
_database_code_depnum_ccdc_archive 'CCDC 999465'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  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.
#
data_24-t-1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H13 Cl2 Co N5 S'
_chemical_formula_weight         425.19

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4790(17)
_cell_length_b                   9.0710(18)
_cell_length_c                   13.536(3)
_cell_angle_alpha                77.03(3)
_cell_angle_beta                 80.74(3)
_cell_angle_gamma                67.56(3)
_cell_volume                     934.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             430
_exptl_absorpt_coefficient_mu    1.322
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8264
_exptl_absorpt_correction_T_max  0.9131
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12443
_diffrn_reflns_av_R_equivalents  0.0754
_diffrn_reflns_av_sigmaI/netI    0.0754
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.14
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3248
_reflns_number_gt                2564
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0148P)²+1.4120P] 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         3248
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1071
_refine_ls_R_factor_gt           0.0782
_refine_ls_wR_factor_ref         0.1126
_refine_ls_wR_factor_gt          0.1029
_refine_ls_goodness_of_fit_ref   1.185
_refine_ls_restrained_S_all      1.185
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.30213(9) 0.90059(10) 0.31030(6) 0.0416(2) Uani 1 1 d . . .
S11 S 0.28608(18) 0.64865(18) 0.38125(11) 0.0447(4) Uani 1 1 d . . .
Cl1 Cl 0.11173(19) 1.1160(2) 0.36928(13) 0.0647(5) Uani 1 1 d . . .
Cl2 Cl 0.2758(2) 0.9227(2) 0.14523(11) 0.0628(5) Uani 1 1 d . . .
N11 N 0.3364(5) 0.7182(5) 0.5587(3) 0.0361(11) Uani 1 1 d . . .
N12 N 0.3031(5) 0.6672(5) 0.6555(3) 0.0352(11) Uani 1 1 d . . .
N13 N 0.2317(5) 0.5555(5) 0.6672(3) 0.0360(11) Uani 1 1 d . . .
N14 N 0.2142(5) 0.5330(5) 0.5776(3) 0.0373(11) Uani 1 1 d . . .
C11 C 0.2791(6) 0.6346(6) 0.5102(4) 0.0359(13) Uani 1 1 d . . .
C12 C 0.1772(7) 0.4716(6) 0.7621(4) 0.0404(14) Uani 1 1 d . . .
C13 C 0.0156(7) 0.4676(8) 0.7729(5) 0.0598(18) Uani 1 1 d . . .
H13 H -0.0586 0.5221 0.7220 0.072 Uiso 1 1 calc R . .
C14 C -0.0341(9) 0.3809(9) 0.8610(6) 0.080(2) Uani 1 1 d . . .
H14 H -0.1428 0.3753 0.8699 0.096 Uiso 1 1 calc R . .
C15 C 0.0760(10) 0.3030(9) 0.9353(5) 0.078(2) Uani 1 1 d . . .
H15 H 0.0406 0.2471 0.9956 0.094 Uiso 1 1 calc R . .
C16 C 0.2365(9) 0.3064(9) 0.9217(5) 0.075(2) Uani 1 1 d . . .
H16 H 0.3113 0.2504 0.9722 0.090 Uiso 1 1 calc R . .
C17 C 0.2901(8) 0.3917(7) 0.8343(4) 0.0550(17) Uani 1 1 d . . .
H17 H 0.4000 0.3946 0.8248 0.066 Uiso 1 1 calc R . .
C18 C 0.3383(6) 0.7268(7) 0.7367(4) 0.0379(13) Uani 1 1 d . . .
C19 C 0.2050(7) 0.8031(7) 0.8011(4) 0.0491(16) Uani 1 1 d . . .
H19 H 0.0934 0.8145 0.7939 0.059 Uiso 1 1 calc R . .
C20 C 0.2403(8) 0.8626(8) 0.8769(4) 0.0618(19) Uani 1 1 d . . .
H20 H 0.1520 0.9143 0.9218 0.074 Uiso 1 1 calc R . .
C21 C 0.4051(8) 0.8456(8) 0.8861(4) 0.0591(18) Uani 1 1 d . . .
H21 H 0.4281 0.8853 0.9376 0.071 Uiso 1 1 calc R . .
C22 C 0.5369(7) 0.7702(8) 0.8197(5) 0.0575(18) Uani 1 1 d . . .
H22 H 0.6484 0.7597 0.8264 0.069 Uiso 1 1 calc R . .
C23 C 0.5043(7) 0.7101(7) 0.7433(4) 0.0466(15) Uani 1 1 d . . .
H23 H 0.5922 0.6598 0.6976 0.056 Uiso 1 1 calc R . .
N31 N 0.5335(6) 0.8835(6) 0.3413(4) 0.0531(14) Uani 1 1 d . . .
C31 C 0.6610(8) 0.8660(7) 0.3660(5) 0.0486(15) Uani 1 1 d . . .
C32 C 0.8266(8) 0.8422(8) 0.3940(6) 0.084(2) Uani 1 1 d . . .
H32A H 0.8713 0.7379 0.4364 0.126 Uiso 1 1 calc R . .
H32B H 0.8163 0.9252 0.4306 0.126 Uiso 1 1 calc R . .
H32C H 0.9029 0.8478 0.3338 0.126 Uiso 1 1 calc R . .


_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 N31 2.013(5) . ?
Co1 Cl1 2.222(2) . ?
Co1 Cl2 2.2376(17) . ?
Co1 S11 2.3182(18) . ?
S11 C11 1.715(5) . ?
N11 N12 1.312(5) . ?
N11 C11 1.359(6) . ?
N12 N13 1.335(5) . ?
N12 C18 1.443(6) . ?
N13 N14 1.313(5) . ?
N13 C12 1.443(6) . ?
N14 C11 1.354(6) . ?
C12 C17 1.360(7) . ?
C12 C13 1.368(7) . ?
C13 C14 1.374(8) . ?
C14 C15 1.364(9) . ?
C15 C16 1.355(9) . ?
C16 C17 1.375(8) . ?
C18 C19 1.368(7) . ?
C18 C23 1.372(7) . ?
C19 C20 1.380(7) . ?
C20 C21 1.369(7) . ?
C21 C22 1.376(8) . ?
C22 C23 1.380(7) . ?
N31 C31 1.125(6) . ?
C31 C32 1.438(7) . ?

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
N31 Co1 Cl1 106.58(16) . . ?
N31 Co1 Cl2 114.49(15) . . ?
Cl1 Co1 Cl2 110.16(8) . . ?
N31 Co1 S11 104.50(15) . . ?
Cl1 Co1 S11 118.11(7) . . ?
Cl2 Co1 S11 103.22(7) . . ?
C11 S11 Co1 105.5(2) . . ?
N12 N11 C11 104.0(4) . . ?
N11 N12 N13 110.5(4) . . ?
N11 N12 C18 123.7(4) . . ?
N13 N12 C18 125.7(4) . . ?
N14 N13 N12 109.7(4) . . ?
N14 N13 C12 123.6(4) . . ?
N12 N13 C12 126.7(4) . . ?
N13 N14 C11 104.6(4) . . ?
N14 C11 N11 111.2(5) . . ?
N14 C11 S11 122.3(4) . . ?
N11 C11 S11 126.6(4) . . ?
C17 C12 C13 122.6(5) . . ?
C17 C12 N13 119.4(5) . . ?
C13 C12 N13 117.9(5) . . ?
C12 C13 C14 118.2(6) . . ?
C15 C14 C13 120.1(6) . . ?
C16 C15 C14 120.4(6) . . ?
C15 C16 C17 120.8(6) . . ?
C12 C17 C16 117.8(6) . . ?
C19 C18 C23 122.7(5) . . ?
C19 C18 N12 119.0(5) . . ?
C23 C18 N12 118.3(5) . . ?
C18 C19 C20 118.3(5) . . ?
C21 C20 C19 120.2(6) . . ?
C20 C21 C22 120.5(6) . . ?
C21 C22 C23 120.2(5) . . ?
C18 C23 C22 118.1(5) . . ?
C31 N31 Co1 174.3(5) . . ?
N31 C31 C32 178.0(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N31 Co1 S11 C11 67.1(2) . . . . ?
Cl1 Co1 S11 C11 -51.04(19) . . . . ?
Cl2 Co1 S11 C11 -172.83(18) . . . . ?
C11 N11 N12 N13 1.1(5) . . . . ?
C11 N11 N12 C18 -178.3(4) . . . . ?
N11 N12 N13 N14 -1.0(5) . . . . ?
C18 N12 N13 N14 178.4(4) . . . . ?
N11 N12 N13 C12 -180.0(4) . . . . ?
C18 N12 N13 C12 -0.6(8) . . . . ?
N12 N13 N14 C11 0.5(5) . . . . ?
C12 N13 N14 C11 179.4(4) . . . . ?
N13 N14 C11 N11 0.2(6) . . . . ?
N13 N14 C11 S11 179.7(3) . . . . ?
N12 N11 C11 N14 -0.8(5) . . . . ?
N12 N11 C11 S11 179.8(4) . . . . ?
Co1 S11 C11 N14 157.7(4) . . . . ?
Co1 S11 C11 N11 -23.0(5) . . . . ?
N14 N13 C12 C17 127.2(6) . . . . ?
N12 N13 C12 C17 -54.0(8) . . . . ?
N14 N13 C12 C13 -48.7(7) . . . . ?
N12 N13 C12 C13 130.1(6) . . . . ?
C17 C12 C13 C14 0.9(10) . . . . ?
N13 C12 C13 C14 176.7(6) . . . . ?
C12 C13 C14 C15 0.6(11) . . . . ?
C13 C14 C15 C16 -1.9(13) . . . . ?
C14 C15 C16 C17 1.7(12) . . . . ?
C13 C12 C17 C16 -1.1(10) . . . . ?
N13 C12 C17 C16 -176.8(6) . . . . ?
C15 C16 C17 C12 -0.2(11) . . . . ?
N11 N12 C18 C19 118.3(6) . . . . ?
N13 N12 C18 C19 -61.0(7) . . . . ?
N11 N12 C18 C23 -59.1(7) . . . . ?
N13 N12 C18 C23 121.6(5) . . . . ?
C23 C18 C19 C20 -1.3(9) . . . . ?
N12 C18 C19 C20 -178.6(5) . . . . ?
C18 C19 C20 C21 0.4(10) . . . . ?
C19 C20 C21 C22 0.4(10) . . . . ?
C20 C21 C22 C23 -0.3(10) . . . . ?
C19 C18 C23 C22 1.4(9) . . . . ?
N12 C18 C23 C22 178.7(5) . . . . ?
C21 C22 C23 C18 -0.6(9) . . . . ?
Cl1 Co1 N31 C31 92(5) . . . . ?
Cl2 Co1 N31 C31 -146(5) . . . . ?
S11 Co1 N31 C31 -34(5) . . . . ?
Co1 N31 C31 C32 131(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.070
_database_code_depnum_ccdc_archive 'CCDC 999466'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  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.
#
data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H13 Br2 Co N5 S'
_chemical_formula_weight         514.11

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.441(7)
_cell_length_b                   9.015(8)
_cell_length_c                   13.725(13)
_cell_angle_alpha                77.19(4)
_cell_angle_beta                 80.64(5)
_cell_angle_gamma                68.94(4)
_cell_volume                     946.4(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      27.50

_exptl_crystal_description       Needle
_exptl_crystal_colour            Green
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.804
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             502
_exptl_absorpt_coefficient_mu    5.245
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_min  0.4202
_exptl_absorpt_correction_T_max  0.5961
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14665
_diffrn_reflns_av_R_equivalents  0.0884
_diffrn_reflns_av_sigmaI/netI    0.0926
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4220
_reflns_number_gt                3290
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0558P)²+4.7396P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4220
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1005
_refine_ls_R_factor_gt           0.0741
_refine_ls_wR_factor_ref         0.1626
_refine_ls_wR_factor_gt          0.1484
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br11 Br 0.11937(10) 0.62258(8) -0.11794(6) 0.0249(2) Uani 1 1 d . . .
Br12 Br 0.26361(10) 0.42043(9) -0.35561(6) 0.0236(2) Uani 1 1 d . . .
Co1 Co 0.31286(13) 0.39526(11) -0.18353(8) 0.0202(3) Uani 1 1 d . . .
S11 S 0.2962(2) 0.1415(2) -0.11584(14) 0.0191(4) Uani 1 1 d . . .
N11 N 0.3448(8) 0.2162(7) 0.0589(4) 0.0176(13) Uani 1 1 d . . .
N12 N 0.3102(7) 0.1658(6) 0.1557(5) 0.0166(13) Uani 1 1 d . . .
N13 N 0.2368(8) 0.0518(7) 0.1673(5) 0.0176(13) Uani 1 1 d . . .
N14 N 0.2209(7) 0.0264(6) 0.0799(5) 0.0167(13) Uani 1 1 d . . .
C11 C 0.2864(9) 0.1290(7) 0.0122(6) 0.0166(15) Uani 1 1 d . . .
C12 C 0.3443(10) 0.2273(8) 0.2359(5) 0.0174(15) Uani 1 1 d . . .
C13 C 0.2059(10) 0.3032(8) 0.3007(6) 0.0237(17) Uani 1 1 d . . .
H13 H 0.0924 0.3124 0.2938 0.028 Uiso 1 1 calc R . .
C14 C 0.2440(10) 0.3639(9) 0.3751(6) 0.0241(17) Uani 1 1 d . . .
H14 H 0.1542 0.4175 0.4199 0.029 Uiso 1 1 calc R . .
C15 C 0.4121(10) 0.3479(9) 0.3856(6) 0.0245(17) Uani 1 1 d . . .
H15 H 0.4360 0.3883 0.4378 0.029 Uiso 1 1 calc R . .
C16 C 0.5436(11) 0.2724(9) 0.3190(6) 0.0276(18) Uani 1 1 d . . .
H16 H 0.6576 0.2614 0.3260 0.033 Uiso 1 1 calc R . .
C17 C 0.5101(10) 0.2133(8) 0.2427(6) 0.0214(16) Uani 1 1 d . . .
H17 H 0.5995 0.1642 0.1962 0.026 Uiso 1 1 calc R . .
C18 C 0.1800(10) -0.0292(8) 0.2625(6) 0.0203(16) Uani 1 1 d . . .
C19 C 0.0137(10) -0.0293(8) 0.2747(6) 0.0237(17) Uani 1 1 d . . .
H19 H -0.0605 0.0254 0.2232 0.028 Uiso 1 1 calc R . .
C20 C -0.0419(11) -0.1116(9) 0.3642(6) 0.0267(18) Uani 1 1 d . . .
H20 H -0.1550 -0.1142 0.3749 0.032 Uiso 1 1 calc R . .
C21 C 0.0716(12) -0.1907(9) 0.4384(6) 0.032(2) Uani 1 1 d . . .
H21 H 0.0340 -0.2458 0.5000 0.039 Uiso 1 1 calc R . .
C22 C 0.2387(11) -0.1899(10) 0.4233(6) 0.033(2) Uani 1 1 d . . .
H22 H 0.3141 -0.2455 0.4741 0.039 Uiso 1 1 calc R . .
C23 C 0.2946(10) -0.1095(9) 0.3356(6) 0.0236(17) Uani 1 1 d . . .
H23 H 0.4081 -0.1081 0.3247 0.028 Uiso 1 1 calc R . .
N31 N 0.5495(8) 0.3823(7) -0.1641(6) 0.0268(16) Uani 1 1 d . . .
C31 C 0.6830(11) 0.3662(8) -0.1497(6) 0.0240(17) Uani 1 1 d . . .
C32 C 0.8590(10) 0.3397(9) -0.1330(7) 0.0294(19) Uani 1 1 d . . .
H32A H 0.9100 0.2293 -0.0973 0.044 Uiso 1 1 calc R . .
H32B H 0.8597 0.4168 -0.0928 0.044 Uiso 1 1 calc R . .
H32C H 0.9251 0.3554 -0.1977 0.044 Uiso 1 1 calc R . .


_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
Br11 Co1 2.369(2) . ?
Br12 Co1 2.412(3) . ?
Co1 N31 2.017(7) . ?
Co1 S11 2.316(3) . ?
S11 C11 1.726(8) . ?
N11 N12 1.327(8) . ?
N11 C11 1.369(9) . ?
N12 N13 1.348(8) . ?
N12 C12 1.445(9) . ?
N13 N14 1.306(9) . ?
N13 C18 1.448(9) . ?
N14 C11 1.357(8) . ?
C12 C17 1.377(11) . ?
C12 C13 1.407(10) . ?
C13 C14 1.389(11) . ?
C13 H13 0.9500 . ?
C14 C15 1.401(11) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(11) . ?
C15 H15 0.9500 . ?
C16 C17 1.383(11) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.387(11) . ?
C18 C23 1.398(11) . ?
C19 C20 1.392(10) . ?
C19 H19 0.9500 . ?
C20 C21 1.403(12) . ?
C20 H20 0.9500 . ?
C21 C22 1.394(12) . ?
C21 H21 0.9500 . ?
C22 C23 1.368(10) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
N31 C31 1.128(10) . ?
C31 C32 1.466(12) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 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
N31 Co1 S11 105.73(19) . . ?
N31 Co1 Br11 107.1(2) . . ?
S11 Co1 Br11 119.30(9) . . ?
N31 Co1 Br12 114.5(2) . . ?
S11 Co1 Br12 101.24(8) . . ?
Br11 Co1 Br12 109.24(7) . . ?
C11 S11 Co1 104.6(2) . . ?
N12 N11 C11 103.7(6) . . ?
N11 N12 N13 109.8(6) . . ?
N11 N12 C12 124.4(6) . . ?
N13 N12 C12 125.7(6) . . ?
N14 N13 N12 110.3(5) . . ?
N14 N13 C18 124.4(6) . . ?
N12 N13 C18 125.3(6) . . ?
N13 N14 C11 104.8(6) . . ?
N14 C11 N11 111.4(6) . . ?
N14 C11 S11 123.1(6) . . ?
N11 C11 S11 125.6(5) . . ?
C17 C12 C13 123.4(7) . . ?
C17 C12 N12 118.1(6) . . ?
C13 C12 N12 118.4(7) . . ?
C14 C13 C12 116.5(8) . . ?
C14 C13 H13 121.7 . . ?
C12 C13 H13 121.7 . . ?
C13 C14 C15 121.4(7) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C16 C15 C14 119.6(8) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C17 C16 C15 120.7(8) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C12 C17 C16 118.4(7) . . ?
C12 C17 H17 120.8 . . ?
C16 C17 H17 120.8 . . ?
C19 C18 C23 122.9(7) . . ?
C19 C18 N13 117.3(7) . . ?
C23 C18 N13 119.7(7) . . ?
C18 C19 C20 118.4(8) . . ?
C18 C19 H19 120.8 . . ?
C20 C19 H19 120.8 . . ?
C19 C20 C21 119.0(7) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C22 C21 C20 121.1(7) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C23 C22 C21 120.3(8) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C18 118.2(8) . . ?
C22 C23 H23 120.9 . . ?
C18 C23 H23 120.9 . . ?
C31 N31 Co1 175.8(6) . . ?
N31 C31 C32 177.7(8) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 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
N31 Co1 S11 C11 72.2(3) . . . . ?
Br11 Co1 S11 C11 -48.3(3) . . . . ?
Br12 Co1 S11 C11 -168.1(2) . . . . ?
C11 N11 N12 N13 0.9(7) . . . . ?
C11 N11 N12 C12 -178.1(6) . . . . ?
N11 N12 N13 N14 -0.4(7) . . . . ?
C12 N12 N13 N14 178.5(6) . . . . ?
N11 N12 N13 C18 -179.3(6) . . . . ?
C12 N12 N13 C18 -0.3(10) . . . . ?
N12 N13 N14 C11 -0.3(7) . . . . ?
C18 N13 N14 C11 178.6(6) . . . . ?
N13 N14 C11 N11 0.8(8) . . . . ?
N13 N14 C11 S11 179.7(5) . . . . ?
N12 N11 C11 N14 -1.0(7) . . . . ?
N12 N11 C11 S11 -179.9(5) . . . . ?
Co1 S11 C11 N14 157.7(5) . . . . ?
Co1 S11 C11 N11 -23.6(6) . . . . ?
N11 N12 C12 C17 -59.4(9) . . . . ?
N13 N12 C12 C17 121.8(7) . . . . ?
N11 N12 C12 C13 118.5(7) . . . . ?
N13 N12 C12 C13 -60.3(9) . . . . ?
C17 C12 C13 C14 -0.8(11) . . . . ?
N12 C12 C13 C14 -178.5(6) . . . . ?
C12 C13 C14 C15 -0.9(11) . . . . ?
C13 C14 C15 C16 1.3(11) . . . . ?
C14 C15 C16 C17 0.0(11) . . . . ?
C13 C12 C17 C16 2.0(11) . . . . ?
N12 C12 C17 C16 179.8(6) . . . . ?
C15 C16 C17 C12 -1.6(11) . . . . ?
N14 N13 C18 C19 -51.1(9) . . . . ?
N12 N13 C18 C19 127.7(7) . . . . ?
N14 N13 C18 C23 126.0(8) . . . . ?
N12 N13 C18 C23 -55.2(9) . . . . ?
C23 C18 C19 C20 0.7(11) . . . . ?
N13 C18 C19 C20 177.7(6) . . . . ?
C18 C19 C20 C21 0.1(11) . . . . ?
C19 C20 C21 C22 -0.9(12) . . . . ?
C20 C21 C22 C23 0.9(13) . . . . ?
C21 C22 C23 C18 -0.1(12) . . . . ?
C19 C18 C23 C22 -0.7(11) . . . . ?
N13 C18 C23 C22 -177.6(7) . . . . ?
S11 Co1 N31 C31 -9(10) . . . . ?
Br11 Co1 N31 C31 119(10) . . . . ?
Br12 Co1 N31 C31 -120(10) . . . . ?
Co1 N31 C31 C32 63(29) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C13 H13 Br11 0.95 3.06 3.802(9) 135.6 2_565
C19 H19 Br11 0.95 3.08 3.697(8) 124.3 2_565
C32 H32B Br11 0.98 2.86 3.575(10) 130.3 2_665
C15 H15 Br12 0.95 2.99 3.689(8) 131.2 1_556

_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         1.942
_refine_diff_density_min         -1.305
_refine_diff_density_rms         0.180
_database_code_depnum_ccdc_archive 'CCDC 999467'
