# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_14

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H34 Br2 Co3 N4 O12'
_chemical_formula_weight         1051.28

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'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   12.9273(11)
_cell_length_b                   9.3874(9)
_cell_length_c                   18.2110(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.861(4)
_cell_angle_gamma                90.00
_cell_volume                     2103.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    14181
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      25.03

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.030
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1050
_exptl_absorpt_coefficient_mu    3.131
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.694
_exptl_absorpt_correction_T_max  0.910
_exptl_absorpt_process_details   
; 
 SADABS (Sheldrick, 1998) 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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  'Bruker X8 Kappa CCD APEX II'
_diffrn_measurement_method       '/w / /f scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14181
_diffrn_reflns_av_R_equivalents  0.0739
_diffrn_reflns_av_sigmaI/netI    0.1434
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.40
_diffrn_reflns_theta_max         25.03
_reflns_number_total             3644
_reflns_number_gt                2262
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_cell_refinement       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT+ (Bruker, 2005)'
_computing_structure_solution    'Siemens SHELXTLTM 5'
_computing_structure_refinement  'Siemens SHELXTLTM 5'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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)+(0.1008P)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         3644
_refine_ls_number_parameters     259
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1120
_refine_ls_R_factor_gt           0.0774
_refine_ls_wR_factor_ref         0.2066
_refine_ls_wR_factor_gt          0.1950
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.004
_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 -0.19989(5) 0.02992(7) 0.07094(4) 0.01195(18) Uani 1 1 d . . .
Co2 Co 0.0000 0.0000 0.0000 0.0103(3) Uani 1 2 d S . .
Br1 Br -0.35085(4) 0.15138(7) 0.09248(3) 0.03027(17) Uani 1 1 d . . .
C11 C 0.0590(4) -0.1624(6) 0.2345(3) 0.0168(14) Uani 1 1 d . . .
C12 C 0.0229(4) -0.2076(6) 0.2953(3) 0.0215(15) Uani 1 1 d . . .
H12A H -0.0501 -0.1978 0.2916 0.026 Uiso 1 1 calc R . .
C13 C 0.0929(4) -0.2660(6) 0.3602(3) 0.0185(15) Uani 1 1 d . . .
H13A H 0.0675 -0.2938 0.4006 0.022 Uiso 1 1 calc R . .
C14 C 0.2025(4) -0.2840(6) 0.3663(3) 0.0153(14) Uani 1 1 d . . .
C15 C 0.2402(4) -0.2403(6) 0.3065(3) 0.0247(16) Uani 1 1 d . . .
H15A H 0.3131 -0.2517 0.3101 0.030 Uiso 1 1 calc R . .
C16 C 0.1695(4) -0.1801(6) 0.2417(3) 0.0214(12) Uani 1 1 d U . .
H16A H 0.1953 -0.1504 0.2018 0.026 Uiso 1 1 calc R . .
C17 C -0.0173(4) -0.1059(5) 0.1624(3) 0.0165(14) Uani 1 1 d . . .
C18 C 0.2767(4) -0.3584(5) 0.4344(3) 0.0181(15) Uani 1 1 d . . .
O11 O 0.0116(3) -0.0977(4) 0.1040(2) 0.0250(11) Uani 1 1 d . . .
O12 O -0.1126(3) -0.0695(4) 0.16429(19) 0.0210(11) Uani 1 1 d . . .
O13 O 0.3736(3) -0.3765(4) 0.4370(2) 0.0225(11) Uani 1 1 d . . .
O14 O 0.2361(3) -0.3957(4) 0.48652(18) 0.0207(10) Uani 1 1 d . . .
C21 C -0.0342(4) 0.3827(5) 0.0344(3) 0.0164(15) Uani 1 1 d . . .
C22 C 0.0281(4) 0.4933(6) 0.0792(4) 0.0269(18) Uani 1 1 d . . .
H22A H 0.0466 0.4884 0.1327 0.032 Uiso 1 1 calc R . .
C23 C 0.0623(5) 0.6088(6) 0.0455(3) 0.0246(17) Uani 1 1 d . . .
H23A H 0.1038 0.6803 0.0761 0.029 Uiso 1 1 calc R . .
C24 C -0.0710(4) 0.2604(5) 0.0719(3) 0.0165(14) Uani 1 1 d . . .
O21 O -0.1094(3) 0.1520(4) 0.02624(19) 0.0159(10) Uani 1 1 d . . .
O22 O -0.0650(3) 0.2617(4) 0.1402(2) 0.0275(11) Uani 1 1 d . . .
N1 N -0.2992(4) 0.5981(6) 0.1729(3) 0.0361(16) Uani 1 1 d . . .
C1 C -0.2160(6) 0.4943(8) 0.2093(5) 0.062(3) Uani 1 1 d . . .
H1A H -0.2228 0.4677 0.2585 0.094 Uiso 1 1 calc R . .
H1B H -0.1455 0.5351 0.2164 0.094 Uiso 1 1 calc R . .
H1C H -0.2246 0.4114 0.1770 0.094 Uiso 1 1 calc R . .
N2 N -0.4360(4) 0.7396(5) 0.1502(3) 0.0321(15) Uani 1 1 d . . .
C2 C -0.6344(6) 0.7301(11) 0.1216(5) 0.080(3) Uani 1 1 d . . .
H2A H -0.6950 0.7819 0.1282 0.121 Uiso 1 1 calc R . .
H2B H -0.6296 0.6387 0.1460 0.121 Uiso 1 1 calc R . .
H2C H -0.6443 0.7174 0.0675 0.121 Uiso 1 1 calc R . .
C3 C -0.5323(6) 0.8115(10) 0.1573(5) 0.069(3) Uani 1 1 d . . .
H3A H -0.5382 0.9043 0.1329 0.083 Uiso 1 1 calc R . .
H3B H -0.5239 0.8263 0.2115 0.083 Uiso 1 1 calc R . .
C4 C -0.3965(6) 0.7474(7) 0.0899(4) 0.044(2) Uani 1 1 d . . .
H4A H -0.4232 0.8053 0.0468 0.053 Uiso 1 1 calc R . .
C5 C -0.3134(5) 0.6587(7) 0.1024(4) 0.040(2) Uani 1 1 d . . .
H5A H -0.2724 0.6410 0.0694 0.048 Uiso 1 1 calc R . .
C6 C -0.3728(5) 0.6487(7) 0.2007(3) 0.0338(19) Uani 1 1 d . . .
H6A H -0.3804 0.6253 0.2484 0.041 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 O14 1.963(3) 4 ?
Co1 O12 1.964(3) . ?
Co1 O21 1.982(4) . ?
Co1 Br1 2.3942(9) . ?
Co2 O13 2.044(3) 4 ?
Co2 O13 2.044(3) 2 ?
Co2 O11 2.067(4) 3 ?
Co2 O11 2.067(4) . ?
Co2 O21 2.163(3) . ?
Co2 O21 2.163(3) 3 ?
C11 C12 1.393(8) . ?
C11 C16 1.404(7) . ?
C11 C17 1.478(6) . ?
C12 C13 1.364(7) . ?
C12 H12A 0.9300 . ?
C13 C14 1.398(7) . ?
C13 H13A 0.9300 . ?
C14 C15 1.385(8) . ?
C14 C18 1.488(6) . ?
C15 C16 1.373(7) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 O11 1.234(7) . ?
C17 O12 1.289(6) . ?
C18 O13 1.250(6) . ?
C18 O14 1.268(7) . ?
O13 Co2 2.044(3) 2_545 ?
O14 Co1 1.963(3) 4_656 ?
C21 C23 1.390(7) 3_565 ?
C21 C22 1.410(7) . ?
C21 C24 1.487(7) . ?
C22 C23 1.384(8) . ?
C22 H22A 0.9300 . ?
C23 C21 1.390(7) 3_565 ?
C23 H23A 0.9300 . ?
C24 O22 1.223(6) . ?
C24 O21 1.312(6) . ?
N1 C6 1.298(8) . ?
N1 C5 1.364(8) . ?
N1 C1 1.452(8) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
N2 C6 1.335(7) . ?
N2 C4 1.347(9) . ?
N2 C3 1.456(9) . ?
C2 C3 1.491(11) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.323(9) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?

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
O14 Co1 O12 111.41(15) 4 . ?
O14 Co1 O21 102.08(15) 4 . ?
O12 Co1 O21 112.07(14) . . ?
O14 Co1 Br1 105.37(11) 4 . ?
O12 Co1 Br1 111.43(12) . . ?
O21 Co1 Br1 113.90(10) . . ?
O13 Co2 O13 180.0(3) 4 2 ?
O13 Co2 O11 85.22(15) 4 3 ?
O13 Co2 O11 94.78(15) 2 3 ?
O13 Co2 O11 94.78(15) 4 . ?
O13 Co2 O11 85.22(15) 2 . ?
O11 Co2 O11 180.0(2) 3 . ?
O13 Co2 O21 91.95(13) 4 . ?
O13 Co2 O21 88.05(13) 2 . ?
O11 Co2 O21 92.34(14) 3 . ?
O11 Co2 O21 87.66(14) . . ?
O13 Co2 O21 88.05(13) 4 3 ?
O13 Co2 O21 91.95(13) 2 3 ?
O11 Co2 O21 87.66(14) 3 3 ?
O11 Co2 O21 92.34(14) . 3 ?
O21 Co2 O21 180.0(2) . 3 ?
C12 C11 C16 118.0(4) . . ?
C12 C11 C17 121.4(5) . . ?
C16 C11 C17 120.6(5) . . ?
C13 C12 C11 121.1(5) . . ?
C13 C12 H12A 119.4 . . ?
C11 C12 H12A 119.4 . . ?
C12 C13 C14 120.3(5) . . ?
C12 C13 H13A 119.9 . . ?
C14 C13 H13A 119.9 . . ?
C15 C14 C13 119.6(4) . . ?
C15 C14 C18 120.1(5) . . ?
C13 C14 C18 120.1(5) . . ?
C16 C15 C14 119.7(5) . . ?
C16 C15 H15A 120.1 . . ?
C14 C15 H15A 120.1 . . ?
C15 C16 C11 121.3(5) . . ?
C15 C16 H16A 119.4 . . ?
C11 C16 H16A 119.4 . . ?
O11 C17 O12 123.5(4) . . ?
O11 C17 C11 119.5(5) . . ?
O12 C17 C11 117.0(5) . . ?
O13 C18 O14 125.0(4) . . ?
O13 C18 C14 118.6(5) . . ?
O14 C18 C14 116.4(5) . . ?
C17 O11 Co2 149.5(4) . . ?
C17 O12 Co1 113.7(3) . . ?
C18 O13 Co2 135.8(4) . 2_545 ?
C18 O14 Co1 126.3(3) . 4_656 ?
C23 C21 C22 118.9(5) 3_565 . ?
C23 C21 C24 120.5(4) 3_565 . ?
C22 C21 C24 120.6(5) . . ?
C23 C22 C21 121.6(6) . . ?
C23 C22 H22A 119.2 . . ?
C21 C22 H22A 119.2 . . ?
C22 C23 C21 119.5(5) . 3_565 ?
C22 C23 H23A 120.2 . . ?
C21 C23 H23A 120.2 3_565 . ?
O22 C24 O21 123.1(5) . . ?
O22 C24 C21 122.0(5) . . ?
O21 C24 C21 114.8(5) . . ?
C24 O21 Co1 110.1(3) . . ?
C24 O21 Co2 120.4(3) . . ?
Co1 O21 Co2 102.56(15) . . ?
C6 N1 C5 108.1(5) . . ?
C6 N1 C1 126.7(6) . . ?
C5 N1 C1 125.2(6) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C6 N2 C4 106.9(5) . . ?
C6 N2 C3 126.4(6) . . ?
C4 N2 C3 126.6(6) . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C3 C2 113.0(7) . . ?
N2 C3 H3A 109.0 . . ?
C2 C3 H3A 109.0 . . ?
N2 C3 H3B 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C5 C4 N2 108.5(6) . . ?
C5 C4 H4A 125.7 . . ?
N2 C4 H4A 125.7 . . ?
C4 C5 N1 107.0(6) . . ?
C4 C5 H5A 126.5 . . ?
N1 C5 H5A 126.5 . . ?
N1 C6 N2 109.4(5) . . ?
N1 C6 H6A 125.3 . . ?
N2 C6 H6A 125.3 . . ?

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
C16 C11 C12 C13 0.6(8) . . . . ?
C17 C11 C12 C13 176.8(5) . . . . ?
C11 C12 C13 C14 -1.2(8) . . . . ?
C12 C13 C14 C15 1.0(8) . . . . ?
C12 C13 C14 C18 -175.0(5) . . . . ?
C13 C14 C15 C16 -0.2(8) . . . . ?
C18 C14 C15 C16 175.8(5) . . . . ?
C14 C15 C16 C11 -0.4(8) . . . . ?
C12 C11 C16 C15 0.2(8) . . . . ?
C17 C11 C16 C15 -176.1(5) . . . . ?
C12 C11 C17 O11 -163.4(5) . . . . ?
C16 C11 C17 O11 12.7(8) . . . . ?
C12 C11 C17 O12 15.5(7) . . . . ?
C16 C11 C17 O12 -168.4(5) . . . . ?
C15 C14 C18 O13 2.0(8) . . . . ?
C13 C14 C18 O13 178.0(5) . . . . ?
C15 C14 C18 O14 -179.7(5) . . . . ?
C13 C14 C18 O14 -3.7(7) . . . . ?
O12 C17 O11 Co2 29.3(10) . . . . ?
C11 C17 O11 Co2 -151.9(5) . . . . ?
O13 Co2 O11 C17 -87.2(7) 4 . . . ?
O13 Co2 O11 C17 92.8(7) 2 . . . ?
O11 Co2 O11 C17 114(30) 3 . . . ?
O21 Co2 O11 C17 4.5(7) . . . . ?
O21 Co2 O11 C17 -175.5(7) 3 . . . ?
O11 C17 O12 Co1 -9.7(6) . . . . ?
C11 C17 O12 Co1 171.5(3) . . . . ?
O14 Co1 O12 C17 79.1(4) 4 . . . ?
O21 Co1 O12 C17 -34.6(4) . . . . ?
Br1 Co1 O12 C17 -163.5(3) . . . . ?
O14 C18 O13 Co2 17.0(8) . . . 2_545 ?
C14 C18 O13 Co2 -164.8(3) . . . 2_545 ?
O13 C18 O14 Co1 -16.1(7) . . . 4_656 ?
C14 C18 O14 Co1 165.6(3) . . . 4_656 ?
C23 C21 C22 C23 -0.5(9) 3_565 . . . ?
C24 C21 C22 C23 -179.3(5) . . . . ?
C21 C22 C23 C21 0.5(9) . . . 3_565 ?
C23 C21 C24 O22 -166.5(5) 3_565 . . . ?
C22 C21 C24 O22 12.3(8) . . . . ?
C23 C21 C24 O21 13.9(7) 3_565 . . . ?
C22 C21 C24 O21 -167.3(5) . . . . ?
O22 C24 O21 Co1 19.9(6) . . . . ?
C21 C24 O21 Co1 -160.5(3) . . . . ?
O22 C24 O21 Co2 -99.0(5) . . . . ?
C21 C24 O21 Co2 80.6(4) . . . . ?
O14 Co1 O21 C24 171.9(3) 4 . . . ?
O12 Co1 O21 C24 -68.8(3) . . . . ?
Br1 Co1 O21 C24 58.8(3) . . . . ?
O14 Co1 O21 Co2 -58.79(15) 4 . . . ?
O12 Co1 O21 Co2 60.53(18) . . . . ?
Br1 Co1 O21 Co2 -171.82(7) . . . . ?
O13 Co2 O21 C24 176.5(4) 4 . . . ?
O13 Co2 O21 C24 -3.5(4) 2 . . . ?
O11 Co2 O21 C24 -98.2(4) 3 . . . ?
O11 Co2 O21 C24 81.8(4) . . . . ?
O21 Co2 O21 C24 -45(65) 3 . . . ?
O13 Co2 O21 Co1 53.85(15) 4 . . . ?
O13 Co2 O21 Co1 -126.15(15) 2 . . . ?
O11 Co2 O21 Co1 139.14(14) 3 . . . ?
O11 Co2 O21 Co1 -40.86(14) . . . . ?
O21 Co2 O21 Co1 -168(65) 3 . . . ?
C6 N2 C3 C2 -91.1(8) . . . . ?
C4 N2 C3 C2 85.8(9) . . . . ?
C6 N2 C4 C5 2.3(7) . . . . ?
C3 N2 C4 C5 -175.1(6) . . . . ?
N2 C4 C5 N1 -1.8(7) . . . . ?
C6 N1 C5 C4 0.7(7) . . . . ?
C1 N1 C5 C4 -179.7(6) . . . . ?
C5 N1 C6 N2 0.8(7) . . . . ?
C1 N1 C6 N2 -178.8(5) . . . . ?
C4 N2 C6 N1 -1.9(7) . . . . ?
C3 N2 C6 N1 175.5(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         2.828
_refine_diff_density_min         -0.730
_refine_diff_density_rms         0.213
_database_code_depnum_ccdc_archive 'CCDC 1006451'
#######################################################################
#
#                 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_14

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H38 Br2 Co3 N4 O12'
_chemical_formula_weight         1079.33

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'
Co Co 0.3494 0.9721 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   12.9773(6)
_cell_length_b                   9.4496(4)
_cell_length_c                   18.2310(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.237(2)
_cell_angle_gamma                90.00
_cell_volume                     2123.37(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            violet
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1082
_exptl_absorpt_coefficient_mu    3.104
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.7070
_exptl_absorpt_correction_T_max  0.8356
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            33494
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.81
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4865
_reflns_number_gt                3999
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0362P)²+3.6809P] 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         4865
_refine_ls_number_parameters     274
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0822
_refine_ls_wR_factor_gt          0.0742
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_restrained_S_all      1.008
_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 0.80325(3) 0.03284(4) 0.07235(2) 0.01275(9) Uani 1 1 d . . .
Co2 Co 1.0000 0.0000 0.0000 0.01060(11) Uani 1 2 d S . .
Br1 Br 0.65423(3) 0.14722(4) 0.09911(2) 0.03333(11) Uani 1 1 d . . .
O1 O 0.89181(15) -0.0709(2) 0.16322(11) 0.0201(4) Uani 1 1 d . . .
O2 O 1.02110(17) -0.0883(2) 0.10655(11) 0.0244(5) Uani 1 1 d . . .
O3 O 1.23276(16) -0.4047(2) 0.48643(11) 0.0217(4) Uani 1 1 d . . .
O4 O 1.37360(15) -0.3723(2) 0.44261(12) 0.0217(4) Uani 1 1 d . . .
O5 O 0.89090(14) 0.15323(19) 0.02546(11) 0.0149(4) Uani 1 1 d . . .
O6 O 0.93400(19) 0.2630(2) 0.13893(12) 0.0275(5) Uani 1 1 d . . .
C1 C 0.9866(2) -0.1044(3) 0.16243(15) 0.0171(6) Uani 1 1 d . . .
C2 C 1.0617(2) -0.1689(3) 0.23442(15) 0.0170(5) Uani 1 1 d . . .
C3 C 1.1717(2) -0.1807(3) 0.24350(17) 0.0223(6) Uani 1 1 d . . .
H3 H 1.1990 -0.1470 0.2041 0.027 Uiso 1 1 calc R . .
C4 C 1.2418(2) -0.2409(3) 0.30928(16) 0.0221(6) Uani 1 1 d . . .
H4 H 1.3170 -0.2487 0.3152 0.027 Uiso 1 1 calc R . .
C5 C 1.2016(2) -0.2900(3) 0.36685(15) 0.0158(5) Uani 1 1 d . . .
C6 C 1.0920(2) -0.2779(3) 0.35820(16) 0.0201(6) Uani 1 1 d . . .
H6 H 1.0648 -0.3117 0.3976 0.024 Uiso 1 1 calc R . .
C7 C 1.0221(2) -0.2170(3) 0.29250(16) 0.0201(6) Uani 1 1 d . . .
H7 H 0.9472 -0.2079 0.2871 0.024 Uiso 1 1 calc R . .
C8 C 1.2759(2) -0.3609(3) 0.43773(16) 0.0155(5) Uani 1 1 d . . .
C9 C 0.9306(2) 0.2610(3) 0.07091(16) 0.0179(6) Uani 1 1 d . . .
C10 C 0.9675(2) 0.3837(3) 0.03416(16) 0.0176(6) Uani 1 1 d . . .
C11 C 0.9446(2) 0.3895(3) -0.04556(16) 0.0192(6) Uani 1 1 d . . .
H11 H 0.9065 0.3139 -0.0768 0.023 Uiso 1 1 calc R . .
C12 C 1.0227(2) 0.4946(3) 0.07975(15) 0.0201(6) Uani 1 1 d . . .
H12 H 1.0382 0.4912 0.1342 0.024 Uiso 1 1 calc R . .
C13 C 0.7810(2) -0.5094(3) 0.20328(15) 0.0497(15) Uani 0.70 1 d PR A 1
H13A H 0.7873 -0.5275 0.2574 0.075 Uiso 0.70 1 calc PR B 1
H13B H 0.8514 -0.4787 0.1997 0.075 Uiso 0.70 1 calc PR C 1
H13C H 0.7583 -0.5962 0.1732 0.075 Uiso 0.70 1 calc PR D 1
C14 C 0.6284(3) -0.3423(4) 0.2023(2) 0.0445(10) Uani 1 1 d . . .
H14 H 0.6202 -0.3630 0.2512 0.053 Uiso 1 1 calc R E 1
C15 C 0.6870(3) -0.3436(5) 0.1039(3) 0.0560(11) Uani 0.70 1 d P A 1
H15 H 0.7277 -0.3665 0.0703 0.067 Uiso 0.70 1 calc PR A 1
C15' C 0.7008(3) -0.3990(4) 0.1729(2) 0.0438(8) Uani 0.30 1 d P A 2
H15' H 0.7536 -0.4679 0.1974 0.053 Uiso 0.30 1 calc PR A 2
C17 C 0.4762(5) -0.1706(6) 0.1575(4) 0.091(2) Uani 1 1 d U . .
H17A H 0.4879 -0.1517 0.2130 0.109 Uiso 1 1 calc R A .
H17B H 0.4733 -0.0781 0.1315 0.109 Uiso 1 1 calc R . .
C16 C 0.6070(3) -0.2509(4) 0.0896(2) 0.0496(11) Uani 1 1 d . . .
H16 H 0.5809 -0.1944 0.0445 0.059 Uiso 1 1 calc R A 1
C18 C 0.3732(3) -0.2402(4) 0.1258(2) 0.111(2) Uani 1 1 d RU A .
H18A H 0.3286 -0.2079 0.1577 0.133 Uiso 1 1 calc R . .
H18B H 0.3404 -0.1971 0.0742 0.133 Uiso 1 1 calc R . .
C19 C 0.3539(5) -0.3751(7) 0.1157(7) 0.157(4) Uani 1 1 d U . .
H19A H 0.3737 -0.4073 0.0708 0.236 Uiso 1 1 calc R A .
H19B H 0.2766 -0.3929 0.1070 0.236 Uiso 1 1 calc R . .
H19C H 0.3969 -0.4266 0.1618 0.236 Uiso 1 1 calc R . .
C13' C 0.7673(17) -0.4198(18) 0.0772(14) 0.088(7) Uani 0.30 1 d P A 2
H13D H 0.8204 -0.4654 0.1213 0.132 Uiso 0.30 1 calc PR A 2
H13E H 0.8046 -0.3529 0.0531 0.132 Uiso 0.30 1 calc PR A 2
H13F H 0.7306 -0.4919 0.0394 0.132 Uiso 0.30 1 calc PR A 2
N1 N 0.7008(3) -0.3990(4) 0.1729(2) 0.0438(8) Uani 0.70 1 d P A 1
N1' N 0.6870(3) -0.3436(5) 0.1039(3) 0.0560(11) Uani 0.30 1 d P A 2
N2 N 0.5693(3) -0.2507(3) 0.15010(18) 0.0392(7) Uani 1 1 d . A .


_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 O1 1.9584(18) . ?
Co1 O3 1.9648(19) 4 ?
Co1 O5 1.9817(19) . ?
Co1 Br1 2.3951(5) . ?
Co2 O4 2.0414(18) 2_755 ?
Co2 O4 2.0414(18) 4 ?
Co2 O2 2.0520(19) 3_755 ?
Co2 O2 2.0521(19) . ?
Co2 O5 2.1744(18) 3_755 ?
Co2 O5 2.1744(18) . ?
O1 C1 1.275(3) . ?
O2 C1 1.244(3) . ?
O3 C8 1.258(3) . ?
O3 Co1 1.9648(19) 4_656 ?
O4 C8 1.248(3) . ?
O4 Co2 2.0414(18) 2_745 ?
O5 C9 1.312(3) . ?
O6 C9 1.227(3) . ?
C1 C2 1.498(4) . ?
C2 C7 1.390(4) . ?
C2 C3 1.390(4) . ?
C3 C4 1.381(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(4) . ?
C5 C8 1.506(3) . ?
C6 C7 1.382(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C9 C10 1.491(4) . ?
C10 C12 1.390(4) . ?
C10 C11 1.391(4) . ?
C11 C12 1.390(4) 3_765 ?
C11 H11 0.9500 . ?
C12 C11 1.390(4) 3_765 ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15' 1.332(5) . ?
C14 N2 1.337(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.320(6) . ?
C15 H15 0.9500 . ?
C15' H15' 0.9500 . ?
C17 C18 1.438(7) . ?
C17 N2 1.468(6) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C16 N2 1.339(4) . ?
C16 H16 0.9500 . ?
C18 C19 1.301(8) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C13' H13D 0.9800 . ?
C13' H13E 0.9800 . ?
C13' H13F 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
O1 Co1 O3 111.67(9) . 4 ?
O1 Co1 O5 112.84(8) . . ?
O3 Co1 O5 101.35(8) 4 . ?
O1 Co1 Br1 110.56(6) . . ?
O3 Co1 Br1 103.68(6) 4 . ?
O5 Co1 Br1 115.97(5) . . ?
O4 Co2 O4 180.0 2_755 4 ?
O4 Co2 O2 95.32(9) 2_755 3_755 ?
O4 Co2 O2 84.68(9) 4 3_755 ?
O4 Co2 O2 84.68(9) 2_755 . ?
O4 Co2 O2 95.32(9) 4 . ?
O2 Co2 O2 180.00(17) 3_755 . ?
O4 Co2 O5 91.75(7) 2_755 3_755 ?
O4 Co2 O5 88.25(7) 4 3_755 ?
O2 Co2 O5 88.37(7) 3_755 3_755 ?
O2 Co2 O5 91.63(7) . 3_755 ?
O4 Co2 O5 88.25(7) 2_755 . ?
O4 Co2 O5 91.75(7) 4 . ?
O2 Co2 O5 91.63(7) 3_755 . ?
O2 Co2 O5 88.37(7) . . ?
O5 Co2 O5 180.00(7) 3_755 . ?
C1 O1 Co1 115.32(18) . . ?
C1 O2 Co2 148.17(19) . . ?
C8 O3 Co1 124.48(17) . 4_656 ?
C8 O4 Co2 136.31(18) . 2_745 ?
C9 O5 Co1 109.75(17) . . ?
C9 O5 Co2 119.89(16) . . ?
Co1 O5 Co2 102.11(8) . . ?
O2 C1 O1 125.1(2) . . ?
O2 C1 C2 117.7(2) . . ?
O1 C1 C2 117.2(2) . . ?
C7 C2 C3 119.6(2) . . ?
C7 C2 C1 120.4(2) . . ?
C3 C2 C1 120.0(3) . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.5(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.1(2) . . ?
C6 C5 C8 119.5(2) . . ?
C4 C5 C8 120.3(2) . . ?
C7 C6 C5 120.3(3) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C2 119.8(3) . . ?
C6 C7 H7 120.1 . . ?
C2 C7 H7 120.1 . . ?
O4 C8 O3 126.0(2) . . ?
O4 C8 C5 117.6(2) . . ?
O3 C8 C5 116.4(2) . . ?
O6 C9 O5 122.2(3) . . ?
O6 C9 C10 121.8(3) . . ?
O5 C9 C10 115.9(2) . . ?
C12 C10 C11 119.8(3) . . ?
C12 C10 C9 119.7(3) . . ?
C11 C10 C9 120.5(2) . . ?
C12 C11 C10 120.3(3) 3_765 . ?
C12 C11 H11 119.9 3_765 . ?
C10 C11 H11 119.9 . . ?
C11 C12 C10 119.9(3) 3_765 . ?
C11 C12 H12 120.0 3_765 . ?
C10 C12 H12 120.0 . . ?
C15' C14 N2 107.0(3) . . ?
C15' C14 H14 126.5 . . ?
N2 C14 H14 126.5 . . ?
C16 C15 H15 125.9 . . ?
C14 C15' H15' 125.6 . . ?
C18 C17 N2 114.5(5) . . ?
C18 C17 H17A 108.6 . . ?
N2 C17 H17A 108.6 . . ?
C18 C17 H17B 108.6 . . ?
N2 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
C15 C16 N2 107.8(3) . . ?
C15 C16 H16 126.1 . . ?
N2 C16 H16 126.1 . . ?
C19 C18 C17 128.2(5) . . ?
C19 C18 H18A 105.2 . . ?
C17 C18 H18A 105.2 . . ?
C19 C18 H18B 105.2 . . ?
C17 C18 H18B 105.2 . . ?
H18A C18 H18B 106.0 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
H13D C13' H13E 109.5 . . ?
H13D C13' H13F 109.5 . . ?
H13E C13' H13F 109.5 . . ?
C14 N2 C16 108.1(3) . . ?
C14 N2 C17 125.0(4) . . ?
C16 N2 C17 126.9(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 Co1 O1 C1 82.5(2) 4 . . . ?
O5 Co1 O1 C1 -30.9(2) . . . . ?
Br1 Co1 O1 C1 -162.63(17) . . . . ?
O4 Co2 O2 C1 108.8(4) 2_755 . . . ?
O4 Co2 O2 C1 -71.2(4) 4 . . . ?
O2 Co2 O2 C1 -52(100) 3_755 . . . ?
O5 Co2 O2 C1 -159.6(4) 3_755 . . . ?
O5 Co2 O2 C1 20.4(4) . . . . ?
O1 Co1 O5 C9 -70.65(18) . . . . ?
O3 Co1 O5 C9 169.79(16) 4 . . . ?
Br1 Co1 O5 C9 58.32(17) . . . . ?
O1 Co1 O5 Co2 57.57(10) . . . . ?
O3 Co1 O5 Co2 -61.99(9) 4 . . . ?
Br1 Co1 O5 Co2 -173.46(4) . . . . ?
O4 Co2 O5 C9 -6.58(19) 2_755 . . . ?
O4 Co2 O5 C9 173.42(19) 4 . . . ?
O2 Co2 O5 C9 -101.85(19) 3_755 . . . ?
O2 Co2 O5 C9 78.15(19) . . . . ?
O5 Co2 O5 C9 87(100) 3_755 . . . ?
O4 Co2 O5 Co1 -128.04(9) 2_755 . . . ?
O4 Co2 O5 Co1 51.96(9) 4 . . . ?
O2 Co2 O5 Co1 136.68(9) 3_755 . . . ?
O2 Co2 O5 Co1 -43.32(9) . . . . ?
O5 Co2 O5 Co1 -35(100) 3_755 . . . ?
Co2 O2 C1 O1 12.1(6) . . . . ?
Co2 O2 C1 C2 -168.2(3) . . . . ?
Co1 O1 C1 O2 -7.2(4) . . . . ?
Co1 O1 C1 C2 173.13(18) . . . . ?
O2 C1 C2 C7 -166.5(3) . . . . ?
O1 C1 C2 C7 13.2(4) . . . . ?
O2 C1 C2 C3 13.7(4) . . . . ?
O1 C1 C2 C3 -166.6(3) . . . . ?
C7 C2 C3 C4 0.6(5) . . . . ?
C1 C2 C3 C4 -179.5(3) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C3 C4 C5 C8 177.7(3) . . . . ?
C4 C5 C6 C7 -0.1(4) . . . . ?
C8 C5 C6 C7 -178.1(3) . . . . ?
C5 C6 C7 C2 0.7(5) . . . . ?
C3 C2 C7 C6 -1.0(5) . . . . ?
C1 C2 C7 C6 179.2(3) . . . . ?
Co2 O4 C8 O3 22.2(5) 2_745 . . . ?
Co2 O4 C8 C5 -157.1(2) 2_745 . . . ?
Co1 O3 C8 O4 -12.1(4) 4_656 . . . ?
Co1 O3 C8 C5 167.13(18) 4_656 . . . ?
C6 C5 C8 O4 178.6(3) . . . . ?
C4 C5 C8 O4 0.6(4) . . . . ?
C6 C5 C8 O3 -0.8(4) . . . . ?
C4 C5 C8 O3 -178.7(3) . . . . ?
Co1 O5 C9 O6 16.6(3) . . . . ?
Co2 O5 C9 O6 -101.0(3) . . . . ?
Co1 O5 C9 C10 -161.10(18) . . . . ?
Co2 O5 C9 C10 81.3(3) . . . . ?
O6 C9 C10 C12 10.3(4) . . . . ?
O5 C9 C10 C12 -172.0(2) . . . . ?
O6 C9 C10 C11 -168.1(3) . . . . ?
O5 C9 C10 C11 9.5(4) . . . . ?
C12 C10 C11 C12 0.3(4) . . . 3_765 ?
C9 C10 C11 C12 178.7(3) . . . 3_765 ?
C11 C10 C12 C11 -0.3(4) . . . 3_765 ?
C9 C10 C12 C11 -178.7(3) . . . 3_765 ?
N2 C17 C18 C19 25.2(10) . . . . ?
C15' C14 N2 C16 -0.8(4) . . . . ?
C15' C14 N2 C17 176.4(4) . . . . ?
C15 C16 N2 C14 1.2(5) . . . . ?
C15 C16 N2 C17 -175.9(4) . . . . ?
C18 C17 N2 C14 -90.5(6) . . . . ?
C18 C17 N2 C16 86.1(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.112
_refine_diff_density_min         -0.808
_refine_diff_density_rms         0.087




_database_code_depnum_ccdc_archive 'CCDC 1006452'
#######################################################################
#
#                 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_14

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H12 Br2 Co3 O12, 2(C8 H15 N2)'
_chemical_formula_sum            'C40 H42 Br2 Co3 N4 O12'
_chemical_formula_weight         1107.39

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'
Co Co 0.3494 0.9721 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_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                   13.0822(12)
_cell_length_b                   9.7472(8)
_cell_length_c                   18.0158(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.963(3)
_cell_angle_gamma                90.00
_cell_volume                     2172.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3099
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      28.13

_exptl_crystal_description       prism
_exptl_crystal_colour            violet
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.693
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1114
_exptl_absorpt_coefficient_mu    3.036
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.702
_exptl_absorpt_correction_T_max  0.833
_exptl_absorpt_process_details   
; 
 SADABS (Sheldrick, 1997) 
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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  'Bruker X8 Kappa CCD APEX II'
_diffrn_measurement_method       'omega/phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18735
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_av_sigmaI/netI    0.0752
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.75
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4969
_reflns_number_gt                3376
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_cell_refinement       'APEX2 '
_computing_data_reduction        'SAINT+ (Bruker, 1997-2005)'
_computing_structure_solution    'SHELXTL (Bruker 2001)'
_computing_structure_refinement  'SHELXTL '
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  '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)+(0.0463P)²+1.8712P] 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         4969
_refine_ls_number_parameters     277
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1142
_refine_ls_wR_factor_gt          0.0994
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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 0.30850(2) -0.04388(3) 1.073137(16) 0.01342(8) Uani 1 1 d . . .
Co2 Co 0.5000 0.0000 1.0000 0.01121(10) Uani 1 2 d S . .
Br1 Br 0.157520(19) -0.14621(3) 1.100893(15) 0.02977(7) Uani 1 1 d . . .
C11 C 0.20229(17) 0.2086(3) 0.86997(12) 0.0166(6) Uani 1 1 d . . .
C12 C 0.24155(18) 0.2648(3) 0.81321(13) 0.0247(7) Uani 1 1 d . . .
H12A H 0.3163 0.2589 0.8193 0.030 Uiso 1 1 calc R . .
C13 C 0.17147(18) 0.3289(3) 0.74820(14) 0.0235(7) Uani 1 1 d . . .
H13A H 0.1981 0.3657 0.7092 0.028 Uiso 1 1 calc R . .
C14 C 0.06129(17) 0.3401(2) 0.73918(12) 0.0168(6) Uani 1 1 d . . .
C15 C 0.02305(18) 0.2852(3) 0.79597(13) 0.0195(6) Uani 1 1 d . . .
H15A H -0.0514 0.2930 0.7905 0.023 Uiso 1 1 calc R . .
C16 C 0.09282(17) 0.2188(3) 0.86093(13) 0.0191(6) Uani 1 1 d . . .
H16A H 0.0658 0.1802 0.8993 0.023 Uiso 1 1 calc R . .
C17 C 0.27679(17) 0.1354(2) 0.93916(13) 0.0163(6) Uani 1 1 d . . .
C18 C -0.01296(18) 0.4070(2) 0.66740(12) 0.0155(6) Uani 1 1 d . . .
O11 O 0.37441(12) 0.12361(17) 0.94273(9) 0.0213(5) Uani 1 1 d . . .
O12 O 0.23727(12) 0.08922(18) 0.98899(8) 0.0215(4) Uani 1 1 d . . .
O13 O -0.10503(12) 0.44661(17) 0.66888(9) 0.0200(4) Uani 1 1 d . . .
O14 O 0.01876(13) 0.41953(18) 0.60935(8) 0.0223(5) Uani 1 1 d . . .
C21 C 0.46745(17) -0.3846(2) 1.03232(13) 0.0187(6) Uani 1 1 d . . .
C22 C 0.50888(19) -0.4984(3) 1.07877(14) 0.0220(6) Uani 1 1 d . . .
H22A H 0.5149 -0.4973 1.1327 0.026 Uiso 1 1 calc R . .
C23 C 0.45861(18) -0.3872(3) 0.95248(13) 0.0198(6) Uani 1 1 d . . .
H23A H 0.4303 -0.3100 0.9201 0.024 Uiso 1 1 calc R . .
C24 C 0.42918(17) -0.2626(3) 1.06669(13) 0.0190(6) Uani 1 1 d . . .
O21 O 0.39241(11) -0.15718(15) 1.02041(8) 0.0141(4) Uani 1 1 d . . .
O22 O 0.42828(14) -0.26376(18) 1.13465(9) 0.0280(5) Uani 1 1 d . . .
N1 N -0.1936(2) 0.6086(3) 0.83553(14) 0.0444(8) Uani 1 1 d . . .
N2 N -0.07448(19) 0.7663(3) 0.84255(13) 0.0405(7) Uani 1 1 d . . .
C1 C -0.2650(3) 0.4928(4) 0.8060(2) 0.0661(13) Uani 1 1 d . . .
H1A H -0.3033 0.4705 0.8431 0.099 Uiso 1 1 calc R . .
H1B H -0.2225 0.4134 0.8000 0.099 Uiso 1 1 calc R . .
H1C H -0.3176 0.5165 0.7550 0.099 Uiso 1 1 calc R . .
C2 C 0.1474(3) 0.5768(4) 0.9267(2) 0.0699(13) Uani 1 1 d . . .
H2A H 0.1715 0.4850 0.9176 0.105 Uiso 1 1 calc R . .
H2B H 0.0724 0.5722 0.9263 0.105 Uiso 1 1 calc R . .
H2C H 0.1936 0.6110 0.9777 0.105 Uiso 1 1 calc R . .
C3 C 0.1546(3) 0.6752(4) 0.8609(2) 0.0625(12) Uani 1 1 d . . .
H3A H 0.2303 0.6766 0.8609 0.075 Uiso 1 1 calc R . .
H3B H 0.1094 0.6378 0.8097 0.075 Uiso 1 1 calc R . .
C4 C 0.1193(3) 0.8220(3) 0.8679(2) 0.0549(11) Uani 1 1 d . . .
H4A H 0.1315 0.8425 0.9240 0.066 Uiso 1 1 calc R . .
H4B H 0.1651 0.8851 0.8494 0.066 Uiso 1 1 calc R . .
C5 C 0.0057(2) 0.8491(4) 0.82339(17) 0.0488(10) Uani 1 1 d . . .
H5A H -0.0094 0.9467 0.8309 0.059 Uiso 1 1 calc R . .
H5B H -0.0042 0.8362 0.7670 0.059 Uiso 1 1 calc R . .
C6 C -0.1274(3) 0.6684(3) 0.79890(17) 0.0415(9) Uani 1 1 d . . .
H6A H -0.1217 0.6418 0.7497 0.050 Uiso 1 1 calc R . .
C7 C -0.1729(3) 0.6749(4) 0.90538(18) 0.0516(10) Uani 1 1 d . . .
H7A H -0.2033 0.6528 0.9451 0.062 Uiso 1 1 calc R . .
C8 C -0.1005(2) 0.7794(3) 0.90893(15) 0.0382(8) Uani 1 1 d . . .
H8A H -0.0747 0.8461 0.9492 0.046 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 O13 1.9712(15) 4_666 ?
Co1 O12 1.9828(16) . ?
Co1 O21 2.0010(16) . ?
Co1 Br1 2.4059(4) . ?
Co2 O11 2.0283(15) . ?
Co2 O11 2.0283(15) 3_657 ?
Co2 O14 2.0596(16) 4_666 ?
Co2 O14 2.0596(16) 2_546 ?
Co2 O21 2.1910(16) 3_657 ?
Co2 O21 2.1910(16) . ?
C11 C16 1.391(3) . ?
C11 C12 1.397(4) . ?
C11 C17 1.491(3) . ?
C12 C13 1.380(3) . ?
C12 H12A 0.9500 . ?
C13 C14 1.401(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.384(3) . ?
C14 C18 1.492(3) . ?
C15 C16 1.388(3) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 O12 1.256(3) . ?
C17 O11 1.263(3) . ?
C18 O14 1.250(3) . ?
C18 O13 1.273(3) . ?
O13 Co1 1.9712(15) 4_565 ?
O14 Co2 2.0596(16) 2_556 ?
C21 C22 1.389(3) . ?
C21 C23 1.405(3) . ?
C21 C24 1.500(4) . ?
C22 C23 1.378(4) 3_647 ?
C22 H22A 0.9500 . ?
C23 C22 1.378(4) 3_647 ?
C23 H23A 0.9500 . ?
C24 O22 1.228(3) . ?
C24 O21 1.312(3) . ?
N1 C7 1.361(4) . ?
N1 C6 1.377(4) . ?
N1 C1 1.452(4) . ?
N2 C6 1.286(4) . ?
N2 C8 1.352(4) . ?
N2 C5 1.451(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.551(6) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.522(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.464(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9500 . ?
C7 C8 1.378(5) . ?
C7 H7A 0.9500 . ?
C8 H8A 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
O13 Co1 O12 110.35(7) 4_666 . ?
O13 Co1 O21 115.69(6) 4_666 . ?
O12 Co1 O21 101.08(7) . . ?
O13 Co1 Br1 107.10(5) 4_666 . ?
O12 Co1 Br1 102.51(5) . . ?
O21 Co1 Br1 118.94(5) . . ?
O11 Co2 O11 180.00(9) . 3_657 ?
O11 Co2 O14 94.90(7) . 4_666 ?
O11 Co2 O14 85.10(7) 3_657 4_666 ?
O11 Co2 O14 85.10(7) . 2_546 ?
O11 Co2 O14 94.90(7) 3_657 2_546 ?
O14 Co2 O14 180.000(1) 4_666 2_546 ?
O11 Co2 O21 87.57(6) . 3_657 ?
O11 Co2 O21 92.43(6) 3_657 3_657 ?
O14 Co2 O21 90.62(6) 4_666 3_657 ?
O14 Co2 O21 89.38(6) 2_546 3_657 ?
O11 Co2 O21 92.43(6) . . ?
O11 Co2 O21 87.57(6) 3_657 . ?
O14 Co2 O21 89.38(6) 4_666 . ?
O14 Co2 O21 90.62(6) 2_546 . ?
O21 Co2 O21 180.00(5) 3_657 . ?
C16 C11 C12 119.7(2) . . ?
C16 C11 C17 120.0(2) . . ?
C12 C11 C17 120.2(2) . . ?
C13 C12 C11 119.9(2) . . ?
C13 C12 H12A 120.1 . . ?
C11 C12 H12A 120.1 . . ?
C12 C13 C14 120.6(2) . . ?
C12 C13 H13A 119.7 . . ?
C14 C13 H13A 119.7 . . ?
C15 C14 C13 119.3(2) . . ?
C15 C14 C18 121.3(2) . . ?
C13 C14 C18 119.3(2) . . ?
C14 C15 C16 120.5(2) . . ?
C14 C15 H15A 119.8 . . ?
C16 C15 H15A 119.8 . . ?
C15 C16 C11 120.1(2) . . ?
C15 C16 H16A 119.9 . . ?
C11 C16 H16A 119.9 . . ?
O12 C17 O11 125.13(19) . . ?
O12 C17 C11 117.4(2) . . ?
O11 C17 C11 117.5(2) . . ?
O14 C18 O13 124.16(19) . . ?
O14 C18 C14 117.9(2) . . ?
O13 C18 C14 117.9(2) . . ?
C17 O11 Co2 135.93(16) . . ?
C17 O12 Co1 125.49(14) . . ?
C18 O13 Co1 113.90(15) . 4_565 ?
C18 O14 Co2 150.28(15) . 2_556 ?
C22 C21 C23 119.3(2) . . ?
C22 C21 C24 120.1(2) . . ?
C23 C21 C24 120.6(2) . . ?
C23 C22 C21 120.8(2) 3_647 . ?
C23 C22 H22A 119.6 3_647 . ?
C21 C22 H22A 119.6 . . ?
C22 C23 C21 119.9(2) 3_647 . ?
C22 C23 H23A 120.0 3_647 . ?
C21 C23 H23A 120.0 . . ?
O22 C24 O21 121.3(2) . . ?
O22 C24 C21 121.1(2) . . ?
O21 C24 C21 117.5(2) . . ?
C24 O21 Co1 105.96(14) . . ?
C24 O21 Co2 122.10(13) . . ?
Co1 O21 Co2 100.09(6) . . ?
C7 N1 C6 106.0(3) . . ?
C7 N1 C1 128.2(3) . . ?
C6 N1 C1 125.7(3) . . ?
C6 N2 C8 111.8(3) . . ?
C6 N2 C5 123.6(3) . . ?
C8 N2 C5 124.6(3) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 C2 115.0(3) . . ?
C4 C3 H3A 108.5 . . ?
C2 C3 H3A 108.5 . . ?
C4 C3 H3B 108.5 . . ?
C2 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
C5 C4 C3 113.9(3) . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
C3 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
N2 C5 C4 116.9(3) . . ?
N2 C5 H5A 108.1 . . ?
C4 C5 H5A 108.1 . . ?
N2 C5 H5B 108.1 . . ?
C4 C5 H5B 108.1 . . ?
H5A C5 H5B 107.3 . . ?
N2 C6 N1 108.5(3) . . ?
N2 C6 H6A 125.7 . . ?
N1 C6 H6A 125.7 . . ?
N1 C7 C8 108.7(3) . . ?
N1 C7 H7A 125.6 . . ?
C8 C7 H7A 125.6 . . ?
N2 C8 C7 104.8(3) . . ?
N2 C8 H8A 127.6 . . ?
C7 C8 H8A 127.6 . . ?

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
C16 C11 C12 C13 -0.6(4) . . . . ?
C17 C11 C12 C13 178.1(2) . . . . ?
C11 C12 C13 C14 1.0(4) . . . . ?
C12 C13 C14 C15 -0.5(4) . . . . ?
C12 C13 C14 C18 -178.6(2) . . . . ?
C13 C14 C15 C16 -0.5(4) . . . . ?
C18 C14 C15 C16 177.6(2) . . . . ?
C14 C15 C16 C11 0.9(4) . . . . ?
C12 C11 C16 C15 -0.4(4) . . . . ?
C17 C11 C16 C15 -179.1(2) . . . . ?
C16 C11 C17 O12 -2.6(3) . . . . ?
C12 C11 C17 O12 178.7(2) . . . . ?
C16 C11 C17 O11 176.8(2) . . . . ?
C12 C11 C17 O11 -1.9(3) . . . . ?
C15 C14 C18 O14 -160.3(2) . . . . ?
C13 C14 C18 O14 17.8(3) . . . . ?
C15 C14 C18 O13 19.0(3) . . . . ?
C13 C14 C18 O13 -162.9(2) . . . . ?
O12 C17 O11 Co2 19.5(4) . . . . ?
C11 C17 O11 Co2 -159.86(16) . . . . ?
O11 Co2 O11 C17 53(100) 3_657 . . . ?
O14 Co2 O11 C17 -69.5(2) 4_666 . . . ?
O14 Co2 O11 C17 110.5(2) 2_546 . . . ?
O21 Co2 O11 C17 -159.9(2) 3_657 . . . ?
O21 Co2 O11 C17 20.1(2) . . . . ?
O11 C17 O12 Co1 -13.1(3) . . . . ?
C11 C17 O12 Co1 166.29(15) . . . . ?
O13 Co1 O12 C17 89.91(19) 4_666 . . . ?
O21 Co1 O12 C17 -33.03(19) . . . . ?
Br1 Co1 O12 C17 -156.30(17) . . . . ?
O14 C18 O13 Co1 -4.5(3) . . . 4_565 ?
C14 C18 O13 Co1 176.28(16) . . . 4_565 ?
O13 C18 O14 Co2 11.2(5) . . . 2_556 ?
C14 C18 O14 Co2 -169.6(2) . . . 2_556 ?
C23 C21 C22 C23 0.1(4) . . . 3_647 ?
C24 C21 C22 C23 178.1(2) . . . 3_647 ?
C22 C21 C23 C22 -0.1(4) . . . 3_647 ?
C24 C21 C23 C22 -178.1(2) . . . 3_647 ?
C22 C21 C24 O22 -3.9(3) . . . . ?
C23 C21 C24 O22 174.0(2) . . . . ?
C22 C21 C24 O21 178.9(2) . . . . ?
C23 C21 C24 O21 -3.1(3) . . . . ?
O22 C24 O21 Co1 -14.3(2) . . . . ?
C21 C24 O21 Co1 162.78(16) . . . . ?
O22 C24 O21 Co2 98.9(2) . . . . ?
C21 C24 O21 Co2 -84.0(2) . . . . ?
O13 Co1 O21 C24 70.71(14) 4_666 . . . ?
O12 Co1 O21 C24 -170.11(13) . . . . ?
Br1 Co1 O21 C24 -58.98(13) . . . . ?
O13 Co1 O21 Co2 -57.04(8) 4_666 . . . ?
O12 Co1 O21 Co2 62.13(7) . . . . ?
Br1 Co1 O21 Co2 173.26(2) . . . . ?
O11 Co2 O21 C24 -170.60(17) . . . . ?
O11 Co2 O21 C24 9.40(17) 3_657 . . . ?
O14 Co2 O21 C24 -75.73(17) 4_666 . . . ?
O14 Co2 O21 C24 104.27(17) 2_546 . . . ?
O21 Co2 O21 C24 -146(72) 3_657 . . . ?
O11 Co2 O21 Co1 -54.41(7) . . . . ?
O11 Co2 O21 Co1 125.59(7) 3_657 . . . ?
O14 Co2 O21 Co1 40.46(6) 4_666 . . . ?
O14 Co2 O21 Co1 -139.54(6) 2_546 . . . ?
O21 Co2 O21 Co1 -30(72) 3_657 . . . ?
C2 C3 C4 C5 -93.8(4) . . . . ?
C6 N2 C5 C4 -105.5(3) . . . . ?
C8 N2 C5 C4 72.4(4) . . . . ?
C3 C4 C5 N2 58.7(4) . . . . ?
C8 N2 C6 N1 -0.3(3) . . . . ?
C5 N2 C6 N1 177.9(3) . . . . ?
C7 N1 C6 N2 -2.3(3) . . . . ?
C1 N1 C6 N2 -178.9(3) . . . . ?
C6 N1 C7 C8 3.9(3) . . . . ?
C1 N1 C7 C8 -179.6(3) . . . . ?
C6 N2 C8 C7 2.6(3) . . . . ?
C5 N2 C8 C7 -175.5(3) . . . . ?
N1 C7 C8 N2 -4.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.143
_refine_diff_density_min         -0.718
_refine_diff_density_rms         0.134


_database_code_depnum_ccdc_archive 'CCDC 1006453'
#######################################################################
#
#                 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_15

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C50 H50 Co3 N4 O16'
_chemical_formula_weight         1139.73

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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   33.093(3)
_cell_length_b                   9.6403(9)
_cell_length_c                   18.5130(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.954(5)
_cell_angle_gamma                90.00
_cell_volume                     5898.3(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5005
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      26.47

_exptl_crystal_description       prism
_exptl_crystal_colour            violet
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2348
_exptl_absorpt_coefficient_mu    0.898
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8551
_exptl_absorpt_correction_T_max  0.9565
_exptl_absorpt_process_details   
; 
 SADABS (Sheldrick, 1998) 
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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  'Bruker X8 Kappa CCD APEX II'
_diffrn_measurement_method       '/w / /f scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20895
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_sigmaI/netI    0.0948
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.70
_diffrn_reflns_theta_max         25.02
_reflns_number_total             5131
_reflns_number_gt                3504
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_cell_refinement       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT+ (Bruker, 2005)'
_computing_structure_solution    'Siemens SHELXTLTM 5'
_computing_structure_refinement  'Siemens SHELXTLTM 5'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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)+(0.1248P)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         5131
_refine_ls_number_parameters     276
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0680
_refine_ls_wR_factor_ref         0.2061
_refine_ls_wR_factor_gt          0.1929
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.015
_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 0.152060(10) 0.29562(3) 0.485805(18) 0.02515(9) Uani 1 1 d . . .
Co2 Co 0.2500 0.2500 0.5000 0.01960(12) Uani 1 2 d S . .
O12 O 0.22613(5) 0.18137(17) 0.40192(9) 0.0289(5) Uani 1 1 d . . .
O32 O 0.20335(5) 0.40590(17) 0.50405(9) 0.0264(5) Uani 1 1 d . . .
O11 O 0.15867(5) 0.17542(19) 0.40142(9) 0.0351(5) Uani 1 1 d . . .
O14 O 0.21623(5) -0.11685(17) 0.05945(9) 0.0287(5) Uani 1 1 d . . .
O13 O 0.15388(5) -0.1900(2) 0.07809(10) 0.0377(5) Uani 1 1 d . . .
C31 C 0.22751(8) 0.6327(2) 0.48001(14) 0.0279(7) Uani 1 1 d . . .
C18 C 0.18609(8) -0.1271(3) 0.09666(14) 0.0308(7) Uani 1 1 d . . .
C32 C 0.24738(8) 0.6409(3) 0.54838(13) 0.0319(7) Uani 1 1 d . . .
H32A H 0.2456 0.5657 0.5812 0.038 Uiso 1 1 calc R . .
O22 O 0.10718(8) 0.4359(3) 0.49823(16) 0.0897(10) Uani 1 1 d . . .
C17 C 0.19248(8) 0.1514(3) 0.37459(13) 0.0300(7) Uani 1 1 d . . .
C34 C 0.20187(8) 0.5097(3) 0.45949(15) 0.0324(7) Uani 1 1 d . . .
C14 C 0.18774(8) -0.0577(3) 0.16957(14) 0.0347(8) Uani 1 1 d . . .
C11 C 0.19147(8) 0.0774(3) 0.30308(14) 0.0344(8) Uani 1 1 d . . .
C33 C 0.23039(9) 0.7426(3) 0.43132(15) 0.0326(7) Uani 1 1 d . . .
H33A H 0.2172 0.7374 0.3846 0.039 Uiso 1 1 calc R . .
C16 C 0.22474(8) 0.0632(3) 0.26541(15) 0.0404(8) Uani 1 1 d . . .
H16A H 0.2496 0.1003 0.2849 0.048 Uiso 1 1 calc R . .
C15 C 0.22432(8) -0.0040(3) 0.19871(14) 0.0379(8) Uani 1 1 d . . .
H15A H 0.2485 -0.0131 0.1735 0.045 Uiso 1 1 calc R . .
C12 C 0.15443(9) 0.0230(4) 0.27428(16) 0.0598(11) Uani 1 1 d . . .
H12A H 0.1305 0.0316 0.3002 0.072 Uiso 1 1 calc R . .
C13 C 0.15345(9) -0.0427(4) 0.20815(17) 0.0646(11) Uani 1 1 d . . .
H13A H 0.1285 -0.0785 0.1886 0.078 Uiso 1 1 calc R . .
O31 O 0.17895(6) 0.51083(19) 0.40386(11) 0.0445(6) Uani 1 1 d . . .
O21 O 0.07901(9) 0.2387(3) 0.47331(19) 0.1076(12) Uani 1 1 d . . .
C24 C 0.07818(10) 0.3636(4) 0.4886(2) 0.0674(12) Uani 1 1 d . . .
C21 C 0.03750(10) 0.4331(4) 0.4951(2) 0.0694(12) Uani 1 1 d . . .
C23 C 0.00338(13) 0.3641(6) 0.4749(3) 0.117(2) Uani 1 1 d . . .
H23A H 0.0044 0.2714 0.4577 0.140 Uiso 1 1 calc R . .
C22 C 0.03499(13) 0.5645(5) 0.5198(3) 0.112(2) Uani 1 1 d . . .
H22A H 0.0592 0.6119 0.5344 0.134 Uiso 1 1 calc R . .
N1 N 0.0813(3) -0.2627(8) 0.3609(5) 0.240(4) Uiso 1 1 d D . .
C1 C 0.0642(4) -0.4101(14) 0.3213(8) 0.393(9) Uiso 1 1 d D . .
H1A H 0.0834 -0.4855 0.3328 0.590 Uiso 1 1 calc R . .
H1B H 0.0617 -0.3971 0.2688 0.590 Uiso 1 1 calc R . .
H1C H 0.0377 -0.4336 0.3392 0.590 Uiso 1 1 calc R . .
C7 C 0.1081(2) -0.2770(8) 0.4070(4) 0.155(3) Uiso 1 1 d . . .
H7A H 0.1245 -0.3574 0.4135 0.186 Uiso 1 1 calc R . .
C8 C 0.0830(2) -0.0744(8) 0.4194(4) 0.178(3) Uiso 1 1 d D . .
H8A H 0.0753 0.0122 0.4388 0.214 Uiso 1 1 calc R . .
C9 C 0.0690(3) -0.1284(10) 0.3624(5) 0.232(4) Uiso 1 1 d D . .
H9A H 0.0524 -0.0834 0.3262 0.278 Uiso 1 1 calc R . .
N2 N 0.11122(17) -0.1607(6) 0.4482(3) 0.1496(19) Uiso 1 1 d . . .
C6 C 0.1369(2) -0.1361(7) 0.4999(4) 0.164(3) Uiso 1 1 d D . .
H6A H 0.1277 -0.0504 0.5235 0.197 Uiso 1 1 calc R . .
H6B H 0.1625 -0.1123 0.4774 0.197 Uiso 1 1 calc R . .
C5 C 0.1477(3) -0.2337(11) 0.5584(5) 0.264(5) Uiso 1 1 d D . .
H5A H 0.1759 -0.2000 0.5656 0.316 Uiso 1 1 calc R . .
H5B H 0.1503 -0.3143 0.5259 0.316 Uiso 1 1 calc R . .
C4 C 0.1491(4) -0.3291(12) 0.6345(6) 0.328(7) Uiso 1 1 d D . .
H4A H 0.1274 -0.3938 0.6176 0.394 Uiso 1 1 calc R . .
H4B H 0.1347 -0.2602 0.6633 0.394 Uiso 1 1 calc R . .
C3 C 0.1661(3) -0.4324(9) 0.7104(5) 0.224(4) Uiso 1 1 d . . .
H3A H 0.1703 -0.3751 0.7545 0.269 Uiso 1 1 calc R . .
H3B H 0.1915 -0.4817 0.7009 0.269 Uiso 1 1 calc R . .
C2 C 0.1211(7) -0.563(2) 0.7197(14) 0.563(14) Uiso 1 1 d . . .
H2A H 0.1268 -0.6235 0.7615 0.845 Uiso 1 1 calc R . .
H2B H 0.1179 -0.6195 0.6758 0.845 Uiso 1 1 calc R . .
H2C H 0.0961 -0.5112 0.7264 0.845 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 1.9664(18) . ?
Co1 O13 1.9871(18) 6_556 ?
Co1 O32 2.0164(16) . ?
Co1 O22 2.030(3) . ?
Co2 O12 2.0520(16) 7_556 ?
Co2 O12 2.0520(16) . ?
Co2 O14 2.0578(17) 6_556 ?
Co2 O14 2.0578(17) 4 ?
Co2 O32 2.1587(16) 7_556 ?
Co2 O32 2.1587(16) . ?
O12 C17 1.233(3) . ?
O32 C34 1.296(3) . ?
O11 C17 1.269(3) . ?
O14 C18 1.245(3) . ?
O14 Co2 2.0578(17) 4_545 ?
O13 C18 1.259(3) . ?
O13 Co1 1.9871(18) 6 ?
C31 C33 1.398(4) . ?
C31 C32 1.398(4) . ?
C31 C34 1.495(4) . ?
C18 C14 1.505(4) . ?
C32 C33 1.384(4) 7_566 ?
C32 H32A 0.9500 . ?
O22 C24 1.192(4) . ?
C17 C11 1.502(4) . ?
C34 O31 1.247(3) . ?
C14 C13 1.379(4) . ?
C14 C15 1.399(4) . ?
C11 C16 1.340(4) . ?
C11 C12 1.412(4) . ?
C33 C32 1.384(4) 7_566 ?
C33 H33A 0.9500 . ?
C16 C15 1.394(4) . ?
C16 H16A 0.9500 . ?
C15 H15A 0.9500 . ?
C12 C13 1.377(4) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?
O21 C24 1.237(5) . ?
C24 C21 1.514(5) . ?
C21 C23 1.347(6) . ?
C21 C22 1.351(7) . ?
C23 C22 1.452(6) 5_566 ?
C23 H23A 0.9500 . ?
C22 C23 1.452(6) 5_566 ?
C22 H22A 0.9500 . ?
N1 C7 1.207(10) . ?
N1 C9 1.358(12) . ?
N1 C1 1.683(15) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C7 N2 1.357(9) . ?
C7 H7A 0.9500 . ?
C8 C9 1.245(10) . ?
C8 N2 1.340(9) . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9500 . ?
N2 C6 1.270(8) . ?
C6 C5 1.465(10) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C5 C4 1.681(13) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C4 C3 1.789(14) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C3 C2 1.96(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 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 O13 112.42(8) . 6_556 ?
O11 Co1 O32 108.47(7) . . ?
O13 Co1 O32 97.94(7) 6_556 . ?
O11 Co1 O22 126.47(10) . . ?
O13 Co1 O22 103.52(10) 6_556 . ?
O32 Co1 O22 104.14(9) . . ?
O12 Co2 O12 180.00(9) 7_556 . ?
O12 Co2 O14 85.57(7) 7_556 6_556 ?
O12 Co2 O14 94.43(7) . 6_556 ?
O12 Co2 O14 94.43(7) 7_556 4 ?
O12 Co2 O14 85.57(7) . 4 ?
O14 Co2 O14 180.00(8) 6_556 4 ?
O12 Co2 O32 90.68(6) 7_556 7_556 ?
O12 Co2 O32 89.32(6) . 7_556 ?
O14 Co2 O32 89.62(6) 6_556 7_556 ?
O14 Co2 O32 90.38(6) 4 7_556 ?
O12 Co2 O32 89.32(6) 7_556 . ?
O12 Co2 O32 90.68(6) . . ?
O14 Co2 O32 90.38(6) 6_556 . ?
O14 Co2 O32 89.62(6) 4 . ?
O32 Co2 O32 180.00(6) 7_556 . ?
C17 O12 Co2 137.46(17) . . ?
C34 O32 Co1 107.25(15) . . ?
C34 O32 Co2 121.25(16) . . ?
Co1 O32 Co2 102.97(7) . . ?
C17 O11 Co1 123.70(16) . . ?
C18 O14 Co2 136.00(16) . 4_545 ?
C18 O13 Co1 118.01(17) . 6 ?
C33 C31 C32 119.7(2) . . ?
C33 C31 C34 119.6(2) . . ?
C32 C31 C34 120.6(2) . . ?
O14 C18 O13 125.3(2) . . ?
O14 C18 C14 117.9(2) . . ?
O13 C18 C14 116.8(2) . . ?
C33 C32 C31 120.7(2) 7_566 . ?
C33 C32 H32A 119.7 7_566 . ?
C31 C32 H32A 119.7 . . ?
C24 O22 Co1 100.5(2) . . ?
O12 C17 O11 126.3(2) . . ?
O12 C17 C11 116.8(2) . . ?
O11 C17 C11 116.8(2) . . ?
O31 C34 O32 122.3(2) . . ?
O31 C34 C31 121.0(2) . . ?
O32 C34 C31 116.6(2) . . ?
C13 C14 C15 118.7(3) . . ?
C13 C14 C18 121.2(2) . . ?
C15 C14 C18 120.1(2) . . ?
C16 C11 C12 119.1(3) . . ?
C16 C11 C17 121.7(2) . . ?
C12 C11 C17 119.2(2) . . ?
C32 C33 C31 119.6(2) 7_566 . ?
C32 C33 H33A 120.2 7_566 . ?
C31 C33 H33A 120.2 . . ?
C11 C16 C15 122.5(3) . . ?
C11 C16 H16A 118.7 . . ?
C15 C16 H16A 118.7 . . ?
C16 C15 C14 118.8(3) . . ?
C16 C15 H15A 120.6 . . ?
C14 C15 H15A 120.6 . . ?
C13 C12 C11 119.1(3) . . ?
C13 C12 H12A 120.4 . . ?
C11 C12 H12A 120.4 . . ?
C12 C13 C14 121.8(3) . . ?
C12 C13 H13A 119.1 . . ?
C14 C13 H13A 119.1 . . ?
O22 C24 O21 125.2(3) . . ?
O22 C24 C21 116.2(4) . . ?
O21 C24 C21 118.7(3) . . ?
C23 C21 C22 119.5(4) . . ?
C23 C21 C24 119.7(4) . . ?
C22 C21 C24 120.8(3) . . ?
C21 C23 C22 118.1(5) . 5_566 ?
C21 C23 H23A 121.0 . . ?
C22 C23 H23A 121.0 5_566 . ?
C21 C22 C23 122.4(4) . 5_566 ?
C21 C22 H22A 118.8 . . ?
C23 C22 H22A 118.8 5_566 . ?
C7 N1 C9 107.8(8) . . ?
C7 N1 C1 115.4(8) . . ?
C9 N1 C1 136.0(9) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C7 N2 109.5(7) . . ?
N1 C7 H7A 125.2 . . ?
N2 C7 H7A 125.2 . . ?
C9 C8 N2 107.5(8) . . ?
C9 C8 H8A 126.3 . . ?
N2 C8 H8A 126.3 . . ?
C8 C9 N1 108.5(8) . . ?
C8 C9 H9A 125.8 . . ?
N1 C9 H9A 125.8 . . ?
C6 N2 C8 127.5(6) . . ?
C6 N2 C7 127.4(6) . . ?
C8 N2 C7 105.0(6) . . ?
N2 C6 C5 124.4(7) . . ?
N2 C6 H6A 106.2 . . ?
C5 C6 H6A 106.2 . . ?
N2 C6 H6B 106.2 . . ?
C5 C6 H6B 106.2 . . ?
H6A C6 H6B 106.4 . . ?
C6 C5 C4 165.1(9) . . ?
C6 C5 H5A 94.6 . . ?
C4 C5 H5A 94.6 . . ?
C6 C5 H5B 94.6 . . ?
C4 C5 H5B 94.6 . . ?
H5A C5 H5B 103.2 . . ?
C5 C4 C3 163.2(10) . . ?
C5 C4 H4A 95.2 . . ?
C3 C4 H4A 95.2 . . ?
C5 C4 H4B 95.2 . . ?
C3 C4 H4B 95.2 . . ?
H4A C4 H4B 103.2 . . ?
C4 C3 C2 102.6(9) . . ?
C4 C3 H3A 111.3 . . ?
C2 C3 H3A 111.3 . . ?
C4 C3 H3B 111.3 . . ?
C2 C3 H3B 111.3 . . ?
H3A C3 H3B 109.2 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 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
O12 Co2 O12 C17 -16(100) 7_556 . . . ?
O14 Co2 O12 C17 43.7(3) 6_556 . . . ?
O14 Co2 O12 C17 -136.3(3) 4 . . . ?
O32 Co2 O12 C17 133.3(2) 7_556 . . . ?
O32 Co2 O12 C17 -46.7(2) . . . . ?
O11 Co1 O32 C34 80.94(17) . . . . ?
O13 Co1 O32 C34 -162.15(16) 6_556 . . . ?
O22 Co1 O32 C34 -55.98(18) . . . . ?
O11 Co1 O32 Co2 -48.04(9) . . . . ?
O13 Co1 O32 Co2 68.87(8) 6_556 . . . ?
O22 Co1 O32 Co2 175.04(10) . . . . ?
O12 Co2 O32 C34 112.03(18) 7_556 . . . ?
O12 Co2 O32 C34 -67.97(18) . . . . ?
O14 Co2 O32 C34 -162.40(18) 6_556 . . . ?
O14 Co2 O32 C34 17.60(18) 4 . . . ?
O32 Co2 O32 C34 -128.3(8) 7_556 . . . ?
O12 Co2 O32 Co1 -128.25(8) 7_556 . . . ?
O12 Co2 O32 Co1 51.75(8) . . . . ?
O14 Co2 O32 Co1 -42.68(8) 6_556 . . . ?
O14 Co2 O32 Co1 137.32(8) 4 . . . ?
O32 Co2 O32 Co1 -8.6(7) 7_556 . . . ?
O13 Co1 O11 C17 -93.2(2) 6_556 . . . ?
O32 Co1 O11 C17 14.0(2) . . . . ?
O22 Co1 O11 C17 138.5(2) . . . . ?
Co2 O14 C18 O13 -46.9(4) 4_545 . . . ?
Co2 O14 C18 C14 133.7(2) 4_545 . . . ?
Co1 O13 C18 O14 5.5(3) 6 . . . ?
Co1 O13 C18 C14 -175.18(17) 6 . . . ?
C33 C31 C32 C33 0.6(4) . . . 7_566 ?
C34 C31 C32 C33 -177.0(3) . . . 7_566 ?
O11 Co1 O22 C24 55.3(3) . . . . ?
O13 Co1 O22 C24 -76.4(3) 6_556 . . . ?
O32 Co1 O22 C24 -178.4(2) . . . . ?
Co2 O12 C17 O11 11.0(4) . . . . ?
Co2 O12 C17 C11 -168.01(17) . . . . ?
Co1 O11 C17 O12 11.0(4) . . . . ?
Co1 O11 C17 C11 -169.92(17) . . . . ?
Co1 O32 C34 O31 -19.2(3) . . . . ?
Co2 O32 C34 O31 98.4(3) . . . . ?
Co1 O32 C34 C31 157.58(19) . . . . ?
Co2 O32 C34 C31 -84.8(3) . . . . ?
C33 C31 C34 O31 -9.3(4) . . . . ?
C32 C31 C34 O31 168.3(3) . . . . ?
C33 C31 C34 O32 173.9(2) . . . . ?
C32 C31 C34 O32 -8.5(4) . . . . ?
O14 C18 C14 C13 168.1(3) . . . . ?
O13 C18 C14 C13 -11.3(4) . . . . ?
O14 C18 C14 C15 -10.3(4) . . . . ?
O13 C18 C14 C15 170.3(2) . . . . ?
O12 C17 C11 C16 -9.9(4) . . . . ?
O11 C17 C11 C16 171.0(3) . . . . ?
O12 C17 C11 C12 171.0(3) . . . . ?
O11 C17 C11 C12 -8.1(4) . . . . ?
C32 C31 C33 C32 -0.6(4) . . . 7_566 ?
C34 C31 C33 C32 177.1(3) . . . 7_566 ?
C12 C11 C16 C15 -0.2(5) . . . . ?
C17 C11 C16 C15 -179.4(3) . . . . ?
C11 C16 C15 C14 0.5(4) . . . . ?
C13 C14 C15 C16 -0.2(4) . . . . ?
C18 C14 C15 C16 178.2(3) . . . . ?
C16 C11 C12 C13 -0.3(5) . . . . ?
C17 C11 C12 C13 178.9(3) . . . . ?
C11 C12 C13 C14 0.5(5) . . . . ?
C15 C14 C13 C12 -0.3(5) . . . . ?
C18 C14 C13 C12 -178.7(3) . . . . ?
Co1 O22 C24 O21 -1.8(5) . . . . ?
Co1 O22 C24 C21 178.9(3) . . . . ?
O22 C24 C21 C23 170.5(4) . . . . ?
O21 C24 C21 C23 -8.9(6) . . . . ?
O22 C24 C21 C22 -8.5(6) . . . . ?
O21 C24 C21 C22 172.1(5) . . . . ?
C22 C21 C23 C22 0.6(9) . . . 5_566 ?
C24 C21 C23 C22 -178.4(4) . . . 5_566 ?
C23 C21 C22 C23 -0.6(9) . . . 5_566 ?
C24 C21 C22 C23 178.4(4) . . . 5_566 ?
C9 N1 C7 N2 8.6(11) . . . . ?
C1 N1 C7 N2 -162.8(8) . . . . ?
N2 C8 C9 N1 12.8(11) . . . . ?
C7 N1 C9 C8 -13.7(12) . . . . ?
C1 N1 C9 C8 155.0(12) . . . . ?
C9 C8 N2 C6 168.6(8) . . . . ?
C9 C8 N2 C7 -7.6(9) . . . . ?
N1 C7 N2 C6 -177.2(8) . . . . ?
N1 C7 N2 C8 -1.1(9) . . . . ?
C8 N2 C6 C5 138.1(9) . . . . ?
C7 N2 C6 C5 -46.6(12) . . . . ?
N2 C6 C5 C4 -83(4) . . . . ?
C6 C5 C4 C3 -156(3) . . . . ?
C5 C4 C3 C2 -143(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         1.305
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.110


_database_code_depnum_ccdc_archive 'CCDC 1006454'
