# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 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.
# 
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#  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 
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#
data_sm025
#TrackingRef 'sm025.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H48 Co2 N32 O8'
_chemical_formula_weight         1198.94

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   'P 21/c'

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

_cell_length_a                   18.5537(5)
_cell_length_b                   20.4481(7)
_cell_length_c                   14.4208(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.001(3)
_cell_angle_gamma                90.00
_cell_volume                     5470.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5425
_cell_measurement_theta_min      2.9899
_cell_measurement_theta_max      32.1731

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            'golden yellow'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2472
_exptl_absorpt_coefficient_mu    0.685
_exptl_absorpt_correction_T_min  0.8105
_exptl_absorpt_correction_T_max  0.8528
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            31738
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_av_sigmaI/netI    0.0742
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         25.00
_reflns_number_total             9616
_reflns_number_gt                5964
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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)+(0.0682P)²+2.3552P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9616
_refine_ls_number_parameters     721
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1020
_refine_ls_R_factor_gt           0.0589
_refine_ls_wR_factor_ref         0.1721
_refine_ls_wR_factor_gt          0.1390
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.001

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 0.63556(3) 0.12440(3) 0.60355(4) 0.0463(2) Uani 1 1 d . . .
Co2 Co 0.13319(3) 0.14799(3) 0.55415(4) 0.04402(19) Uani 1 1 d . . .
N1 N 0.56801(18) 0.07348(18) 0.6769(3) 0.0529(10) Uani 1 1 d . . .
H1A H 0.5735 0.0839 0.7373 0.063 Uiso 1 1 calc R . .
H1B H 0.5225 0.0833 0.6592 0.063 Uiso 1 1 calc R . .
N2 N 0.68638(18) 0.04141(17) 0.5870(2) 0.0485(9) Uani 1 1 d . . .
H2A H 0.6779 0.0260 0.5294 0.058 Uiso 1 1 calc R . .
H2B H 0.7342 0.0476 0.5943 0.058 Uiso 1 1 calc R . .
N3 N 0.58102(19) 0.11273(18) 0.4873(3) 0.0530(10) Uani 1 1 d . . .
H3A H 0.5668 0.0708 0.4817 0.064 Uiso 1 1 calc R . .
H3B H 0.5415 0.1382 0.4872 0.064 Uiso 1 1 calc R . .
N4 N 0.70398(18) 0.17306(18) 0.5289(2) 0.0521(9) Uani 1 1 d . . .
H4A H 0.7169 0.2101 0.5586 0.063 Uiso 1 1 calc R . .
H4B H 0.7439 0.1489 0.5207 0.063 Uiso 1 1 calc R . .
N5 N 0.69613(18) 0.13930(18) 0.7094(3) 0.0499(9) Uani 1 1 d . . .
N6 N 0.7667(2) 0.1275(2) 0.7055(3) 0.0561(10) Uani 1 1 d . . .
N7 N 0.6778(2) 0.1667(2) 0.7873(3) 0.0726(13) Uani 1 1 d . . .
N8 N 0.7379(2) 0.1733(2) 0.8396(3) 0.0763(13) Uani 1 1 d . . .
N9 N 0.9889(2) 0.1194(2) 0.7842(3) 0.0766(13) Uani 1 1 d . . .
N10 N 0.58155(18) 0.20191(18) 0.6264(3) 0.0514(9) Uani 1 1 d . . .
N11 N 0.6066(2) 0.2616(2) 0.6352(4) 0.0866(16) Uani 1 1 d . . .
N12 N 0.5507(2) 0.3012(2) 0.6500(4) 0.0852(15) Uani 1 1 d . . .
N13 N 0.50976(18) 0.20040(18) 0.6343(2) 0.0487(9) Uani 1 1 d . . .
N14 N 0.2946(2) 0.2586(2) 0.6836(3) 0.0629(11) Uani 1 1 d . . .
N15 N 0.08134(19) 0.07993(18) 0.6203(2) 0.0501(9) Uani 1 1 d . . .
H15A H 0.0437 0.0976 0.6498 0.060 Uiso 1 1 calc R . .
H15B H 0.0642 0.0500 0.5798 0.060 Uiso 1 1 calc R . .
N16 N 0.20544(18) 0.13995(18) 0.6536(2) 0.0498(9) Uani 1 1 d . . .
H16A H 0.2449 0.1200 0.6319 0.060 Uiso 1 1 calc R . .
H16B H 0.2183 0.1800 0.6737 0.060 Uiso 1 1 calc R . .
N17 N 0.18134(18) 0.08288(18) 0.4780(2) 0.0470(9) Uani 1 1 d . . .
H17A H 0.2293 0.0897 0.4800 0.056 Uiso 1 1 calc R . .
H17B H 0.1727 0.0426 0.5003 0.056 Uiso 1 1 calc R . .
N18 N 0.06228(18) 0.15194(18) 0.4520(2) 0.0487(9) Uani 1 1 d . . .
H18A H 0.0176 0.1488 0.4748 0.058 Uiso 1 1 calc R . .
H18B H 0.0659 0.1907 0.4228 0.058 Uiso 1 1 calc R . .
N19 N 0.19111(18) 0.21215(18) 0.4950(3) 0.0492(9) Uani 1 1 d . . .
N20 N 0.26110(19) 0.20017(19) 0.4807(3) 0.0544(10) Uani 1 1 d . . .
N21 N 0.1722(2) 0.2703(2) 0.4655(3) 0.0678(12) Uani 1 1 d . . .
N22 N 0.2312(2) 0.2991(2) 0.4317(3) 0.0704(12) Uani 1 1 d . . .
N23 N 0.4801(2) 0.2237(2) 0.4113(3) 0.0699(12) Uani 1 1 d . . .
N24 N 0.08084(18) 0.21273(18) 0.6228(2) 0.0478(9) Uani 1 1 d . . .
N25 N 0.01041(18) 0.22084(19) 0.6096(2) 0.0487(9) Uani 1 1 d . . .
N26 N 0.1056(2) 0.2497(2) 0.6912(3) 0.0721(13) Uani 1 1 d . . .
N27 N 0.0494(2) 0.2835(2) 0.7236(3) 0.0712(13) Uani 1 1 d . . .
N28 N -0.2062(2) 0.2768(2) 0.6342(3) 0.0606(11) Uani 1 1 d . . .
C1 C 0.5807(3) 0.0020(2) 0.6644(4) 0.0632(13) Uani 1 1 d . . .
H1C H 0.5560 -0.0137 0.6089 0.076 Uiso 1 1 calc R . .
H1D H 0.5632 -0.0222 0.7173 0.076 Uiso 1 1 calc R . .
C2 C 0.6611(2) -0.0063(2) 0.6560(4) 0.0610(13) Uani 1 1 d . . .
H2C H 0.6849 0.0014 0.7155 0.073 Uiso 1 1 calc R . .
H2D H 0.6723 -0.0504 0.6361 0.073 Uiso 1 1 calc R . .
C3 C 0.6272(3) 0.1305(3) 0.4088(3) 0.0658(14) Uani 1 1 d . . .
H3C H 0.5977 0.1411 0.3546 0.079 Uiso 1 1 calc R . .
H3D H 0.6586 0.0944 0.3934 0.079 Uiso 1 1 calc R . .
C4 C 0.6712(3) 0.1892(3) 0.4387(4) 0.0667(14) Uani 1 1 d . . .
H4C H 0.7083 0.1983 0.3939 0.080 Uiso 1 1 calc R . .
H4D H 0.6407 0.2275 0.4439 0.080 Uiso 1 1 calc R . .
C5 C 0.7903(3) 0.1492(2) 0.7879(3) 0.0548(12) Uani 1 1 d . . .
C6 C 0.8665(3) 0.1492(3) 0.8170(3) 0.0561(12) Uani 1 1 d . . .
C7 C 0.8887(3) 0.1802(3) 0.8967(4) 0.0776(17) Uani 1 1 d . . .
H7 H 0.8555 0.2002 0.9350 0.093 Uiso 1 1 calc R . .
C8 C 0.9617(3) 0.1810(3) 0.9192(4) 0.089(2) Uani 1 1 d . . .
H8 H 0.9783 0.2023 0.9725 0.107 Uiso 1 1 calc R . .
C9 C 1.0089(3) 0.1505(3) 0.8624(4) 0.0858(19) Uani 1 1 d . . .
H9 H 1.0576 0.1512 0.8787 0.103 Uiso 1 1 calc R . .
C10 C 0.9181(3) 0.1193(3) 0.7640(4) 0.0652(14) Uani 1 1 d . . .
H10 H 0.9028 0.0976 0.7106 0.078 Uiso 1 1 calc R . .
C11 C 0.4927(2) 0.2629(2) 0.6487(3) 0.0512(11) Uani 1 1 d . . .
C12 C 0.4185(2) 0.2856(2) 0.6615(3) 0.0500(11) Uani 1 1 d . . .
C13 C 0.4019(3) 0.3511(3) 0.6608(4) 0.0698(15) Uani 1 1 d . . .
H13 H 0.4377 0.3825 0.6539 0.084 Uiso 1 1 calc R . .
C14 C 0.3305(3) 0.3691(3) 0.6706(4) 0.0776(17) Uani 1 1 d . . .
H14 H 0.3172 0.4130 0.6688 0.093 Uiso 1 1 calc R . .
C15 C 0.2796(3) 0.3214(3) 0.6830(4) 0.0713(15) Uani 1 1 d . . .
H15 H 0.2320 0.3342 0.6914 0.086 Uiso 1 1 calc R . .
C16 C 0.3631(2) 0.2420(2) 0.6722(3) 0.0539(12) Uani 1 1 d . . .
H16 H 0.3743 0.1976 0.6713 0.065 Uiso 1 1 calc R . .
C17 C 0.1304(3) 0.0480(2) 0.6883(3) 0.0626(13) Uani 1 1 d . . .
H17C H 0.1604 0.0160 0.6579 0.075 Uiso 1 1 calc R . .
H17D H 0.1031 0.0261 0.7359 0.075 Uiso 1 1 calc R . .
C18 C 0.1765(3) 0.1020(3) 0.7307(3) 0.0631(13) Uani 1 1 d . . .
H18C H 0.1476 0.1298 0.7700 0.076 Uiso 1 1 calc R . .
H18D H 0.2155 0.0835 0.7679 0.076 Uiso 1 1 calc R . .
C19 C 0.1543(2) 0.0876(3) 0.3807(3) 0.0573(13) Uani 1 1 d . . .
H19A H 0.1646 0.0476 0.3473 0.069 Uiso 1 1 calc R . .
H19B H 0.1772 0.1238 0.3492 0.069 Uiso 1 1 calc R . .
C20 C 0.0741(2) 0.0985(3) 0.3851(3) 0.0569(12) Uani 1 1 d . . .
H20A H 0.0549 0.1104 0.3244 0.068 Uiso 1 1 calc R . .
H20B H 0.0502 0.0589 0.4054 0.068 Uiso 1 1 calc R . .
C21 C 0.2842(2) 0.2551(2) 0.4425(3) 0.0508(11) Uani 1 1 d . . .
C22 C 0.3598(2) 0.2662(3) 0.4178(3) 0.0550(12) Uani 1 1 d . . .
C23 C 0.3828(3) 0.3246(3) 0.3825(4) 0.0755(16) Uani 1 1 d . . .
H23 H 0.3503 0.3585 0.3716 0.091 Uiso 1 1 calc R . .
C24 C 0.4551(3) 0.3324(3) 0.3634(4) 0.0781(17) Uani 1 1 d . . .
H24 H 0.4722 0.3719 0.3409 0.094 Uiso 1 1 calc R . .
C25 C 0.5002(3) 0.2816(3) 0.3779(4) 0.0757(17) Uani 1 1 d . . .
H25 H 0.5485 0.2874 0.3637 0.091 Uiso 1 1 calc R . .
C26 C 0.4110(3) 0.2175(3) 0.4310(3) 0.0638(14) Uani 1 1 d . . .
H26 H 0.3958 0.1779 0.4554 0.077 Uiso 1 1 calc R . .
C27 C -0.0078(2) 0.2647(2) 0.6723(3) 0.0490(11) Uani 1 1 d . . .
C28 C -0.0819(2) 0.2875(2) 0.6833(3) 0.0503(11) Uani 1 1 d . . .
C29 C -0.1017(3) 0.3326(3) 0.7481(4) 0.0754(16) Uani 1 1 d . . .
H29 H -0.0672 0.3521 0.7867 0.090 Uiso 1 1 calc R . .
C30 C -0.1739(3) 0.3489(3) 0.7555(4) 0.0817(18) Uani 1 1 d . . .
H30 H -0.1885 0.3793 0.7995 0.098 Uiso 1 1 calc R . .
C31 C -0.2229(3) 0.3204(3) 0.6985(4) 0.0665(14) Uani 1 1 d . . .
H31 H -0.2711 0.3319 0.7045 0.080 Uiso 1 1 calc R . .
C32 C -0.1366(2) 0.2609(2) 0.6284(3) 0.0531(12) Uani 1 1 d . . .
H32 H -0.1240 0.2299 0.5845 0.064 Uiso 1 1 calc R . .
N111 N 0.3759(2) 0.0488(2) 0.6157(4) 0.0672(12) Uani 1 1 d . . .
N222 N 0.8810(2) 0.0843(2) 0.4860(3) 0.0537(10) Uani 1 1 d . . .
O007 O 0.8925(2) 0.14270(19) 0.4734(3) 0.0794(11) Uani 1 1 d . . .
O011 O 0.31401(19) 0.0401(2) 0.5836(3) 0.0857(12) Uani 1 1 d . . .
O111 O 0.4286(2) 0.0325(2) 0.5676(3) 0.0969(14) Uani 1 1 d . . .
O222 O 0.3853(2) 0.0735(2) 0.6920(3) 0.1038(15) Uani 1 1 d . . .
O555 O 0.81762(17) 0.06285(17) 0.4836(2) 0.0678(10) Uani 1 1 d . . .
O666 O 0.93210(19) 0.04581(18) 0.4999(3) 0.0848(12) Uani 1 1 d . . .
N333 N 0.6182(5) 0.4587(4) 0.5266(5) 0.140(3) Uani 1 1 d . . .
O888 O 0.5849(4) 0.4727(3) 0.3783(4) 0.164(3) Uani 1 1 d . . .
O777 O 0.1974(5) 0.0149(5) 0.1692(10) 0.274(5) Uani 1 1 d . . .
N444 N 0.1353(16) 0.0264(10) 0.0393(15) 0.359(15) Uani 1 1 d . . .
C333 C 0.147(3) 0.034(3) 0.082(2) 0.65(5) Uani 1 1 d . . .
C111 C 0.073(3) 0.0664(16) 0.107(2) 0.65(4) Uani 1 1 d . . .
C555 C 0.6183(10) 0.4632(8) 0.6263(8) 0.277(9) Uani 1 1 d . . .
C666 C 0.5970(10) 0.4746(15) 0.4583(15) 0.41(2) Uani 1 1 d . . .
C444 C 0.6527(12) 0.3975(9) 0.5099(16) 0.350(13) Uani 1 1 d . . .
C222 C 0.1374(19) 0.0019(16) -0.0476(12) 0.50(2) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N5 1.904(4) . ?
Co1 N10 1.907(4) . ?
Co1 N4 1.952(4) . ?
Co1 N1 1.955(4) . ?
Co1 N3 1.958(4) . ?
Co1 N2 1.958(3) . ?
Co2 N19 1.907(4) . ?
Co2 N24 1.926(4) . ?
Co2 N15 1.951(3) . ?
Co2 N16 1.953(3) . ?
Co2 N17 1.952(3) . ?
Co2 N18 1.960(3) . ?
N1 C1 1.491(6) . ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?
N2 C2 1.475(6) . ?
N2 H2A 0.9000 . ?
N2 H2B 0.9000 . ?
N3 C3 1.476(6) . ?
N3 H3A 0.9000 . ?
N3 H3B 0.9000 . ?
N4 C4 1.463(6) . ?
N4 H4A 0.9000 . ?
N4 H4B 0.9000 . ?
N5 N7 1.305(5) . ?
N5 N6 1.333(5) . ?
N6 C5 1.334(6) . ?
N7 N8 1.341(5) . ?
N8 C5 1.332(6) . ?
N9 C9 1.341(7) . ?
N9 C10 1.340(6) . ?
N10 N11 1.311(5) . ?
N10 N13 1.339(4) . ?
N11 N12 1.336(5) . ?
N12 C11 1.331(6) . ?
N13 C11 1.334(5) . ?
N14 C15 1.315(7) . ?
N14 C16 1.330(5) . ?
N15 C17 1.478(6) . ?
N15 H15A 0.9000 . ?
N15 H15B 0.9000 . ?
N16 C18 1.465(6) . ?
N16 H16A 0.9000 . ?
N16 H16B 0.9000 . ?
N17 C19 1.485(5) . ?
N17 H17A 0.9000 . ?
N17 H17B 0.9000 . ?
N18 C20 1.477(6) . ?
N18 H18A 0.9000 . ?
N18 H18B 0.9000 . ?
N19 N21 1.308(5) . ?
N19 N20 1.341(5) . ?
N20 C21 1.325(5) . ?
N21 N22 1.341(5) . ?
N22 C21 1.341(6) . ?
N23 C26 1.325(6) . ?
N23 C25 1.334(7) . ?
N24 N26 1.318(5) . ?
N24 N25 1.328(4) . ?
N25 C27 1.322(5) . ?
N26 N27 1.342(5) . ?
N27 C27 1.340(5) . ?
N28 C31 1.327(6) . ?
N28 C32 1.335(5) . ?
C1 C2 1.510(6) . ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C2 H2C 0.9700 . ?
C2 H2D 0.9700 . ?
C3 C4 1.511(7) . ?
C3 H3C 0.9700 . ?
C3 H3D 0.9700 . ?
C4 H4C 0.9700 . ?
C4 H4D 0.9700 . ?
C5 C6 1.467(6) . ?
C6 C7 1.369(6) . ?
C6 C10 1.378(6) . ?
C7 C8 1.388(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.361(8) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.467(6) . ?
C12 C16 1.371(6) . ?
C12 C13 1.375(6) . ?
C13 C14 1.385(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.372(8) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.518(7) . ?
C17 H17C 0.9700 . ?
C17 H17D 0.9700 . ?
C18 H18C 0.9700 . ?
C18 H18D 0.9700 . ?
C19 C20 1.507(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.470(6) . ?
C22 C23 1.370(7) . ?
C22 C26 1.386(7) . ?
C23 C24 1.384(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.347(8) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C28 1.463(6) . ?
C28 C29 1.369(6) . ?
C28 C32 1.387(6) . ?
C29 C30 1.387(6) . ?
C29 H29 0.9300 . ?
C30 C31 1.348(7) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
N111 O222 1.220(5) . ?
N111 O011 1.243(5) . ?
N111 O111 1.253(5) . ?
N222 O007 1.226(5) . ?
N222 O666 1.246(5) . ?
N222 O555 1.256(4) . ?
N333 C666 1.104(15) . ?
N333 C444 1.428(16) . ?
N333 C555 1.440(12) . ?
O888 C666 1.171(19) . ?
O777 C333 1.60(4) . ?
N444 C333 0.67(3) . ?
N444 C222 1.35(3) . ?
N444 C111 1.73(4) . ?
C333 C111 1.58(7) . ?
C333 C222 1.99(4) . ?
C666 C444 2.02(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 Co1 N10 91.90(16) . . ?
N5 Co1 N4 88.87(16) . . ?
N10 Co1 N4 91.17(16) . . ?
N5 Co1 N1 91.51(16) . . ?
N10 Co1 N1 90.31(16) . . ?
N4 Co1 N1 178.46(16) . . ?
N5 Co1 N3 174.28(16) . . ?
N10 Co1 N3 89.08(15) . . ?
N4 Co1 N3 85.48(15) . . ?
N1 Co1 N3 94.13(15) . . ?
N5 Co1 N2 87.56(15) . . ?
N10 Co1 N2 175.61(16) . . ?
N4 Co1 N2 93.18(15) . . ?
N1 Co1 N2 85.35(15) . . ?
N3 Co1 N2 91.88(15) . . ?
N19 Co2 N24 92.88(15) . . ?
N19 Co2 N15 175.11(15) . . ?
N24 Co2 N15 88.94(15) . . ?
N19 Co2 N16 90.08(15) . . ?
N24 Co2 N16 91.51(15) . . ?
N15 Co2 N16 85.34(15) . . ?
N19 Co2 N17 87.17(15) . . ?
N24 Co2 N17 176.16(15) . . ?
N15 Co2 N17 91.32(15) . . ?
N16 Co2 N17 92.33(15) . . ?
N19 Co2 N18 90.66(15) . . ?
N24 Co2 N18 91.16(15) . . ?
N15 Co2 N18 93.84(15) . . ?
N16 Co2 N18 177.19(15) . . ?
N17 Co2 N18 85.00(14) . . ?
C1 N1 Co1 110.7(3) . . ?
C1 N1 H1A 109.5 . . ?
Co1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
Co1 N1 H1B 109.5 . . ?
H1A N1 H1B 108.1 . . ?
C2 N2 Co1 109.4(3) . . ?
C2 N2 H2A 109.8 . . ?
Co1 N2 H2A 109.8 . . ?
C2 N2 H2B 109.8 . . ?
Co1 N2 H2B 109.8 . . ?
H2A N2 H2B 108.2 . . ?
C3 N3 Co1 109.2(3) . . ?
C3 N3 H3A 109.8 . . ?
Co1 N3 H3A 109.8 . . ?
C3 N3 H3B 109.8 . . ?
Co1 N3 H3B 109.8 . . ?
H3A N3 H3B 108.3 . . ?
C4 N4 Co1 110.0(3) . . ?
C4 N4 H4A 109.7 . . ?
Co1 N4 H4A 109.7 . . ?
C4 N4 H4B 109.7 . . ?
Co1 N4 H4B 109.7 . . ?
H4A N4 H4B 108.2 . . ?
N7 N5 N6 112.6(4) . . ?
N7 N5 Co1 126.9(3) . . ?
N6 N5 Co1 120.3(3) . . ?
N5 N6 C5 102.2(4) . . ?
N5 N7 N8 107.6(4) . . ?
C5 N8 N7 104.8(4) . . ?
C9 N9 C10 116.0(5) . . ?
N11 N10 N13 111.4(4) . . ?
N11 N10 Co1 127.1(3) . . ?
N13 N10 Co1 121.5(3) . . ?
N10 N11 N12 107.8(4) . . ?
C11 N12 N11 105.7(4) . . ?
C11 N13 N10 103.3(3) . . ?
C15 N14 C16 116.8(4) . . ?
C17 N15 Co2 109.6(3) . . ?
C17 N15 H15A 109.7 . . ?
Co2 N15 H15A 109.7 . . ?
C17 N15 H15B 109.7 . . ?
Co2 N15 H15B 109.7 . . ?
H15A N15 H15B 108.2 . . ?
C18 N16 Co2 110.2(3) . . ?
C18 N16 H16A 109.6 . . ?
Co2 N16 H16A 109.6 . . ?
C18 N16 H16B 109.6 . . ?
Co2 N16 H16B 109.6 . . ?
H16A N16 H16B 108.1 . . ?
C19 N17 Co2 109.7(3) . . ?
C19 N17 H17A 109.7 . . ?
Co2 N17 H17A 109.7 . . ?
C19 N17 H17B 109.7 . . ?
Co2 N17 H17B 109.7 . . ?
H17A N17 H17B 108.2 . . ?
C20 N18 Co2 110.8(3) . . ?
C20 N18 H18A 109.5 . . ?
Co2 N18 H18A 109.5 . . ?
C20 N18 H18B 109.5 . . ?
Co2 N18 H18B 109.5 . . ?
H18A N18 H18B 108.1 . . ?
N21 N19 N20 111.8(4) . . ?
N21 N19 Co2 128.4(3) . . ?
N20 N19 Co2 119.9(3) . . ?
C21 N20 N19 103.3(4) . . ?
N19 N21 N22 107.5(4) . . ?
C21 N22 N21 105.4(4) . . ?
C26 N23 C25 116.2(5) . . ?
N26 N24 N25 111.4(3) . . ?
N26 N24 Co2 127.3(3) . . ?
N25 N24 Co2 121.1(3) . . ?
C27 N25 N24 104.4(3) . . ?
N24 N26 N27 107.1(4) . . ?
C27 N27 N26 105.8(4) . . ?
C31 N28 C32 116.3(4) . . ?
N1 C1 C2 106.1(4) . . ?
N1 C1 H1C 110.5 . . ?
C2 C1 H1C 110.5 . . ?
N1 C1 H1D 110.5 . . ?
C2 C1 H1D 110.5 . . ?
H1C C1 H1D 108.7 . . ?
N2 C2 C1 107.8(4) . . ?
N2 C2 H2C 110.1 . . ?
C1 C2 H2C 110.1 . . ?
N2 C2 H2D 110.1 . . ?
C1 C2 H2D 110.1 . . ?
H2C C2 H2D 108.5 . . ?
N3 C3 C4 107.2(4) . . ?
N3 C3 H3C 110.3 . . ?
C4 C3 H3C 110.3 . . ?
N3 C3 H3D 110.3 . . ?
C4 C3 H3D 110.3 . . ?
H3C C3 H3D 108.5 . . ?
N4 C4 C3 106.8(4) . . ?
N4 C4 H4C 110.4 . . ?
C3 C4 H4C 110.4 . . ?
N4 C4 H4D 110.4 . . ?
C3 C4 H4D 110.4 . . ?
H4C C4 H4D 108.6 . . ?
N8 C5 N6 112.9(4) . . ?
N8 C5 C6 123.3(4) . . ?
N6 C5 C6 123.7(4) . . ?
C7 C6 C10 118.0(5) . . ?
C7 C6 C5 120.9(5) . . ?
C10 C6 C5 121.1(4) . . ?
C6 C7 C8 118.7(5) . . ?
C6 C7 H7 120.7 . . ?
C8 C7 H7 120.7 . . ?
C9 C8 C7 119.2(5) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
N9 C9 C8 123.6(5) . . ?
N9 C9 H9 118.2 . . ?
C8 C9 H9 118.2 . . ?
N9 C10 C6 124.5(5) . . ?
N9 C10 H10 117.7 . . ?
C6 C10 H10 117.7 . . ?
N12 C11 N13 111.8(4) . . ?
N12 C11 C12 124.9(4) . . ?
N13 C11 C12 123.2(4) . . ?
C16 C12 C13 117.8(4) . . ?
C16 C12 C11 121.0(4) . . ?
C13 C12 C11 121.2(4) . . ?
C12 C13 C14 118.2(5) . . ?
C12 C13 H13 120.9 . . ?
C14 C13 H13 120.9 . . ?
C15 C14 C13 119.1(5) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
N14 C15 C14 123.4(5) . . ?
N14 C15 H15 118.3 . . ?
C14 C15 H15 118.3 . . ?
N14 C16 C12 124.6(5) . . ?
N14 C16 H16 117.7 . . ?
C12 C16 H16 117.7 . . ?
N15 C17 C18 106.4(4) . . ?
N15 C17 H17C 110.4 . . ?
C18 C17 H17C 110.4 . . ?
N15 C17 H17D 110.4 . . ?
C18 C17 H17D 110.4 . . ?
H17C C17 H17D 108.6 . . ?
N16 C18 C17 106.9(4) . . ?
N16 C18 H18C 110.3 . . ?
C17 C18 H18C 110.3 . . ?
N16 C18 H18D 110.3 . . ?
C17 C18 H18D 110.3 . . ?
H18C C18 H18D 108.6 . . ?
N17 C19 C20 106.7(3) . . ?
N17 C19 H19A 110.4 . . ?
C20 C19 H19A 110.4 . . ?
N17 C19 H19B 110.4 . . ?
C20 C19 H19B 110.4 . . ?
H19A C19 H19B 108.6 . . ?
N18 C20 C19 107.2(4) . . ?
N18 C20 H20A 110.3 . . ?
C19 C20 H20A 110.3 . . ?
N18 C20 H20B 110.3 . . ?
C19 C20 H20B 110.3 . . ?
H20A C20 H20B 108.5 . . ?
N20 C21 N22 112.0(4) . . ?
N20 C21 C22 123.3(4) . . ?
N22 C21 C22 124.7(4) . . ?
C23 C22 C26 117.3(5) . . ?
C23 C22 C21 122.0(5) . . ?
C26 C22 C21 120.7(5) . . ?
C22 C23 C24 118.9(5) . . ?
C22 C23 H23 120.5 . . ?
C24 C23 H23 120.5 . . ?
C25 C24 C23 118.9(6) . . ?
C25 C24 H24 120.6 . . ?
C23 C24 H24 120.6 . . ?
N23 C25 C24 124.2(5) . . ?
N23 C25 H25 117.9 . . ?
C24 C25 H25 117.9 . . ?
N23 C26 C22 124.4(5) . . ?
N23 C26 H26 117.8 . . ?
C22 C26 H26 117.8 . . ?
N25 C27 N27 111.3(4) . . ?
N25 C27 C28 122.9(4) . . ?
N27 C27 C28 125.9(4) . . ?
C29 C28 C32 116.8(4) . . ?
C29 C28 C27 123.6(4) . . ?
C32 C28 C27 119.6(4) . . ?
C28 C29 C30 119.1(5) . . ?
C28 C29 H29 120.5 . . ?
C30 C29 H29 120.5 . . ?
C31 C30 C29 119.4(5) . . ?
C31 C30 H30 120.3 . . ?
C29 C30 H30 120.3 . . ?
N28 C31 C30 123.7(5) . . ?
N28 C31 H31 118.1 . . ?
C30 C31 H31 118.1 . . ?
N28 C32 C28 124.7(4) . . ?
N28 C32 H32 117.7 . . ?
C28 C32 H32 117.7 . . ?
O222 N111 O011 120.8(5) . . ?
O222 N111 O111 120.5(5) . . ?
O011 N111 O111 118.7(5) . . ?
O007 N222 O666 120.4(4) . . ?
O007 N222 O555 120.1(4) . . ?
O666 N222 O555 119.5(4) . . ?
C666 N333 C444 105.1(19) . . ?
C666 N333 C555 150(2) . . ?
C444 N333 C555 103.4(13) . . ?
C333 N444 C222 158(8) . . ?
C333 N444 C111 66(7) . . ?
C222 N444 C111 137(3) . . ?
N444 C333 O777 148(9) . . ?
N444 C333 C111 92(7) . . ?
O777 C333 C111 115(3) . . ?
N444 C333 C222 15(5) . . ?
O777 C333 C222 135(4) . . ?
C111 C333 C222 107(3) . . ?
C333 C111 N444 22.8(13) . . ?
N333 C666 O888 158(3) . . ?
N333 C666 C444 43.0(12) . . ?
O888 C666 C444 115(3) . . ?
N333 C444 C666 31.8(9) . . ?
N444 C222 C333 7(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
N5 Co1 N1 C1 -99.4(3) . . . . ?
N10 Co1 N1 C1 168.7(3) . . . . ?
N4 Co1 N1 C1 5(6) . . . . ?
N3 Co1 N1 C1 79.6(3) . . . . ?
N2 Co1 N1 C1 -11.9(3) . . . . ?
N5 Co1 N2 C2 75.8(3) . . . . ?
N10 Co1 N2 C2 -7(2) . . . . ?
N4 Co1 N2 C2 164.6(3) . . . . ?
N1 Co1 N2 C2 -15.9(3) . . . . ?
N3 Co1 N2 C2 -109.9(3) . . . . ?
N5 Co1 N3 C3 5.2(17) . . . . ?
N10 Co1 N3 C3 105.1(3) . . . . ?
N4 Co1 N3 C3 13.9(3) . . . . ?
N1 Co1 N3 C3 -164.6(3) . . . . ?
N2 Co1 N3 C3 -79.2(3) . . . . ?
N5 Co1 N4 C4 -166.3(3) . . . . ?
N10 Co1 N4 C4 -74.4(3) . . . . ?
N1 Co1 N4 C4 90(6) . . . . ?
N3 Co1 N4 C4 14.6(3) . . . . ?
N2 Co1 N4 C4 106.2(3) . . . . ?
N10 Co1 N5 N7 33.1(4) . . . . ?
N4 Co1 N5 N7 124.2(4) . . . . ?
N1 Co1 N5 N7 -57.3(4) . . . . ?
N3 Co1 N5 N7 132.9(15) . . . . ?
N2 Co1 N5 N7 -142.6(4) . . . . ?
N10 Co1 N5 N6 -139.9(3) . . . . ?
N4 Co1 N5 N6 -48.7(3) . . . . ?
N1 Co1 N5 N6 129.8(3) . . . . ?
N3 Co1 N5 N6 -40.1(17) . . . . ?
N2 Co1 N5 N6 44.5(3) . . . . ?
N7 N5 N6 C5 0.6(5) . . . . ?
Co1 N5 N6 C5 174.5(3) . . . . ?
N6 N5 N7 N8 -0.8(6) . . . . ?
Co1 N5 N7 N8 -174.2(3) . . . . ?
N5 N7 N8 C5 0.5(6) . . . . ?
N5 Co1 N10 N11 55.6(5) . . . . ?
N4 Co1 N10 N11 -33.3(5) . . . . ?
N1 Co1 N10 N11 147.2(5) . . . . ?
N3 Co1 N10 N11 -118.7(5) . . . . ?
N2 Co1 N10 N11 138.5(19) . . . . ?
N5 Co1 N10 N13 -125.3(3) . . . . ?
N4 Co1 N10 N13 145.8(3) . . . . ?
N1 Co1 N10 N13 -33.8(3) . . . . ?
N3 Co1 N10 N13 60.4(3) . . . . ?
N2 Co1 N10 N13 -42(2) . . . . ?
N13 N10 N11 N12 0.5(6) . . . . ?
Co1 N10 N11 N12 179.6(4) . . . . ?
N10 N11 N12 C11 -0.6(7) . . . . ?
N11 N10 N13 C11 -0.2(5) . . . . ?
Co1 N10 N13 C11 -179.4(3) . . . . ?
N19 Co2 N15 C17 5(2) . . . . ?
N24 Co2 N15 C17 -107.2(3) . . . . ?
N16 Co2 N15 C17 -15.6(3) . . . . ?
N17 Co2 N15 C17 76.6(3) . . . . ?
N18 Co2 N15 C17 161.7(3) . . . . ?
N19 Co2 N16 C18 168.7(3) . . . . ?
N24 Co2 N16 C18 75.8(3) . . . . ?
N15 Co2 N16 C18 -13.0(3) . . . . ?
N17 Co2 N16 C18 -104.2(3) . . . . ?
N18 Co2 N16 C18 -86(3) . . . . ?
N19 Co2 N17 C19 -73.5(3) . . . . ?
N24 Co2 N17 C19 17(2) . . . . ?
N15 Co2 N17 C19 111.1(3) . . . . ?
N16 Co2 N17 C19 -163.5(3) . . . . ?
N18 Co2 N17 C19 17.4(3) . . . . ?
N19 Co2 N18 C20 97.5(3) . . . . ?
N24 Co2 N18 C20 -169.6(3) . . . . ?
N15 Co2 N18 C20 -80.6(3) . . . . ?
N16 Co2 N18 C20 -8(3) . . . . ?
N17 Co2 N18 C20 10.4(3) . . . . ?
N24 Co2 N19 N21 -37.3(4) . . . . ?
N15 Co2 N19 N21 -149.0(17) . . . . ?
N16 Co2 N19 N21 -128.8(4) . . . . ?
N17 Co2 N19 N21 138.9(4) . . . . ?
N18 Co2 N19 N21 53.9(4) . . . . ?
N24 Co2 N19 N20 141.5(3) . . . . ?
N15 Co2 N19 N20 30(2) . . . . ?
N16 Co2 N19 N20 50.0(3) . . . . ?
N17 Co2 N19 N20 -42.3(3) . . . . ?
N18 Co2 N19 N20 -127.3(3) . . . . ?
N21 N19 N20 C21 1.3(5) . . . . ?
Co2 N19 N20 C21 -177.7(3) . . . . ?
N20 N19 N21 N22 -1.1(5) . . . . ?
Co2 N19 N21 N22 177.8(3) . . . . ?
N19 N21 N22 C21 0.4(6) . . . . ?
N19 Co2 N24 N26 -69.2(4) . . . . ?
N15 Co2 N24 N26 106.3(4) . . . . ?
N16 Co2 N24 N26 20.9(4) . . . . ?
N17 Co2 N24 N26 -160(2) . . . . ?
N18 Co2 N24 N26 -159.9(4) . . . . ?
N19 Co2 N24 N25 116.7(3) . . . . ?
N15 Co2 N24 N25 -67.8(3) . . . . ?
N16 Co2 N24 N25 -153.1(3) . . . . ?
N17 Co2 N24 N25 26(2) . . . . ?
N18 Co2 N24 N25 26.0(3) . . . . ?
N26 N24 N25 C27 0.2(5) . . . . ?
Co2 N24 N25 C27 175.2(3) . . . . ?
N25 N24 N26 N27 -0.3(5) . . . . ?
Co2 N24 N26 N27 -174.8(3) . . . . ?
N24 N26 N27 C27 0.2(6) . . . . ?
Co1 N1 C1 C2 36.1(4) . . . . ?
Co1 N2 C2 C1 40.0(4) . . . . ?
N1 C1 C2 N2 -49.1(5) . . . . ?
Co1 N3 C3 C4 -38.4(5) . . . . ?
Co1 N4 C4 C3 -38.9(4) . . . . ?
N3 C3 C4 N4 50.3(5) . . . . ?
N7 N8 C5 N6 -0.2(6) . . . . ?
N7 N8 C5 C6 177.5(5) . . . . ?
N5 N6 C5 N8 -0.3(6) . . . . ?
N5 N6 C5 C6 -177.9(4) . . . . ?
N8 C5 C6 C7 -6.4(8) . . . . ?
N6 C5 C6 C7 170.9(5) . . . . ?
N8 C5 C6 C10 175.1(5) . . . . ?
N6 C5 C6 C10 -7.6(8) . . . . ?
C10 C6 C7 C8 1.2(9) . . . . ?
C5 C6 C7 C8 -177.3(5) . . . . ?
C6 C7 C8 C9 -0.9(10) . . . . ?
C10 N9 C9 C8 -0.4(9) . . . . ?
C7 C8 C9 N9 0.5(11) . . . . ?
C9 N9 C10 C6 0.8(8) . . . . ?
C7 C6 C10 N9 -1.2(8) . . . . ?
C5 C6 C10 N9 177.3(5) . . . . ?
N11 N12 C11 N13 0.5(7) . . . . ?
N11 N12 C11 C12 -179.6(5) . . . . ?
N10 N13 C11 N12 -0.2(6) . . . . ?
N10 N13 C11 C12 179.9(4) . . . . ?
N12 C11 C12 C16 -170.7(5) . . . . ?
N13 C11 C12 C16 9.1(7) . . . . ?
N12 C11 C12 C13 11.1(8) . . . . ?
N13 C11 C12 C13 -169.1(5) . . . . ?
C16 C12 C13 C14 -0.1(8) . . . . ?
C11 C12 C13 C14 178.1(5) . . . . ?
C12 C13 C14 C15 1.7(9) . . . . ?
C16 N14 C15 C14 0.5(8) . . . . ?
C13 C14 C15 N14 -1.9(9) . . . . ?
C15 N14 C16 C12 1.2(7) . . . . ?
C13 C12 C16 N14 -1.4(7) . . . . ?
C11 C12 C16 N14 -179.7(4) . . . . ?
Co2 N15 C17 C18 39.6(4) . . . . ?
Co2 N16 C18 C17 37.8(5) . . . . ?
N15 C17 C18 N16 -50.0(5) . . . . ?
Co2 N17 C19 C20 -40.8(4) . . . . ?
Co2 N18 C20 C19 -35.3(4) . . . . ?
N17 C19 C20 N18 48.9(5) . . . . ?
N19 N20 C21 N22 -1.1(5) . . . . ?
N19 N20 C21 C22 177.3(4) . . . . ?
N21 N22 C21 N20 0.5(6) . . . . ?
N21 N22 C21 C22 -177.9(4) . . . . ?
N20 C21 C22 C23 -176.8(5) . . . . ?
N22 C21 C22 C23 1.4(8) . . . . ?
N20 C21 C22 C26 2.2(7) . . . . ?
N22 C21 C22 C26 -179.6(5) . . . . ?
C26 C22 C23 C24 -0.9(8) . . . . ?
C21 C22 C23 C24 178.1(5) . . . . ?
C22 C23 C24 C25 1.7(9) . . . . ?
C26 N23 C25 C24 -0.3(8) . . . . ?
C23 C24 C25 N23 -1.1(9) . . . . ?
C25 N23 C26 C22 1.1(8) . . . . ?
C23 C22 C26 N23 -0.5(8) . . . . ?
C21 C22 C26 N23 -179.5(4) . . . . ?
N24 N25 C27 N27 -0.1(5) . . . . ?
N24 N25 C27 C28 -179.0(4) . . . . ?
N26 N27 C27 N25 -0.1(6) . . . . ?
N26 N27 C27 C28 178.8(5) . . . . ?
N25 C27 C28 C29 179.8(5) . . . . ?
N27 C27 C28 C29 1.1(8) . . . . ?
N25 C27 C28 C32 2.4(7) . . . . ?
N27 C27 C28 C32 -176.4(5) . . . . ?
C32 C28 C29 C30 0.2(8) . . . . ?
C27 C28 C29 C30 -177.3(5) . . . . ?
C28 C29 C30 C31 -0.5(10) . . . . ?
C32 N28 C31 C30 0.8(8) . . . . ?
C29 C30 C31 N28 -0.1(10) . . . . ?
C31 N28 C32 C28 -1.1(7) . . . . ?
C29 C28 C32 N28 0.6(8) . . . . ?
C27 C28 C32 N28 178.2(4) . . . . ?
C222 N444 C333 O777 -32(18) . . . . ?
C111 N444 C333 O777 148(9) . . . . ?
C222 N444 C333 C111 -180(100) . . . . ?
C111 N444 C333 C222 180(100) . . . . ?
O777 C333 C111 N444 -162(6) . . . . ?
C222 C333 C111 N444 0(3) . . . . ?
C222 N444 C111 C333 180(6) . . . . ?
C444 N333 C666 O888 -1(5) . . . . ?
C555 N333 C666 O888 -162(3) . . . . ?
C555 N333 C666 C444 -162(3) . . . . ?
C555 N333 C444 C666 170.7(16) . . . . ?
O888 C666 C444 N333 180(2) . . . . ?
C111 N444 C222 C333 -179(100) . . . . ?
O777 C333 C222 N444 157(14) . . . . ?
C111 C333 C222 N444 0(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.729
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.064
_database_code_depnum_ccdc_archive 'CCDC 933043'
#######################################################################
#
#                 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_sm028
#TrackingRef 'sm028.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H24 Co N15 O4'
_chemical_formula_weight         597.47

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   'P 21/c'

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

_cell_length_a                   11.6957(6)
_cell_length_b                   18.9480(6)
_cell_length_c                   12.5618(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.388(4)
_cell_angle_gamma                90.00
_cell_volume                     2781.40(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5109
_cell_measurement_theta_min      3.1656
_cell_measurement_theta_max      32.4663

_exptl_crystal_description       block
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_absorpt_coefficient_mu    0.673
_exptl_absorpt_correction_T_min  0.8085
_exptl_absorpt_correction_T_max  0.8716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15822
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_sigmaI/netI    0.0414
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4888
_reflns_number_gt                3766
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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)+(0.0746P)²+1.6889P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    RIDING
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4888
_refine_ls_number_parameters     361
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1467
_refine_ls_wR_factor_gt          0.1328
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.036
_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
Co01 Co 0.36784(4) 0.16380(2) 0.65436(3) 0.03897(17) Uani 1 1 d . . .
N1 N 0.2804(3) 0.07646(14) 0.6347(2) 0.0472(7) Uani 1 1 d . . .
H1A H 0.3217 0.0399 0.6610 0.057 Uiso 1 1 calc R . .
H1B H 0.2155 0.0792 0.6706 0.057 Uiso 1 1 calc R . .
N2 N 0.3259(3) 0.18243(15) 0.5046(2) 0.0500(7) Uani 1 1 d . . .
H2A H 0.3056 0.2280 0.4962 0.060 Uiso 1 1 calc R . .
H2B H 0.3862 0.1740 0.4642 0.060 Uiso 1 1 calc R . .
N3 N 0.4603(3) 0.24942(13) 0.6677(2) 0.0444(7) Uani 1 1 d . . .
H3A H 0.4428 0.2786 0.6128 0.053 Uiso 1 1 calc R . .
H3B H 0.4448 0.2720 0.7285 0.053 Uiso 1 1 calc R . .
N4 N 0.5107(2) 0.11798(14) 0.6182(2) 0.0449(7) Uani 1 1 d . . .
H4A H 0.5370 0.0916 0.6735 0.054 Uiso 1 1 calc R . .
H4B H 0.4979 0.0893 0.5618 0.054 Uiso 1 1 calc R . .
N5 N 0.2335(3) 0.21432(14) 0.6927(2) 0.0473(7) Uani 1 1 d . . .
N6 N 0.2019(3) 0.27546(17) 0.6518(3) 0.0688(10) Uani 1 1 d . . .
N7 N 0.1069(3) 0.29596(19) 0.6991(3) 0.0723(10) Uani 1 1 d . . .
N8 N 0.1636(3) 0.19423(16) 0.7677(2) 0.0588(8) Uani 1 1 d . . .
N9 N -0.1985(4) 0.2436(3) 0.9723(4) 0.0955(14) Uani 1 1 d . . .
N10 N 0.3949(2) 0.14252(14) 0.80259(19) 0.0423(7) Uani 1 1 d . . .
N11 N 0.4171(3) 0.19010(14) 0.8766(2) 0.0493(7) Uani 1 1 d . . .
N12 N 0.4054(3) 0.15875(14) 0.9709(2) 0.0511(8) Uani 1 1 d . . .
N13 N 0.3695(3) 0.07986(13) 0.8441(2) 0.0445(7) Uani 1 1 d . . .
N14 N 0.3318(3) -0.06461(18) 1.1871(3) 0.0674(9) Uani 1 1 d . . .
C1 C 0.2521(4) 0.0647(2) 0.5202(3) 0.0619(10) Uani 1 1 d . . .
H1C H 0.1851 0.0348 0.5114 0.074 Uiso 1 1 calc R . .
H1D H 0.3155 0.0419 0.4866 0.074 Uiso 1 1 calc R . .
C2 C 0.2291(4) 0.1360(2) 0.4708(3) 0.0592(10) Uani 1 1 d . . .
H2C H 0.2237 0.1322 0.3938 0.071 Uiso 1 1 calc R . .
H2D H 0.1577 0.1551 0.4949 0.071 Uiso 1 1 calc R . .
C3 C 0.5831(4) 0.2312(2) 0.6683(3) 0.0593(10) Uani 1 1 d . . .
H3C H 0.6100 0.2175 0.7394 0.071 Uiso 1 1 calc R . .
H3D H 0.6274 0.2716 0.6463 0.071 Uiso 1 1 calc R . .
C4 C 0.5968(3) 0.17149(19) 0.5926(3) 0.0571(10) Uani 1 1 d . . .
H4C H 0.5846 0.1876 0.5197 0.069 Uiso 1 1 calc R . .
H4D H 0.6732 0.1518 0.6007 0.069 Uiso 1 1 calc R . .
C5 C 0.0860(3) 0.2451(2) 0.7690(3) 0.0549(9) Uani 1 1 d . . .
C6 C -0.0112(4) 0.2452(2) 0.8395(3) 0.0596(10) Uani 1 1 d . . .
C7 C -0.0113(4) 0.2034(3) 0.9290(4) 0.0780(13) Uani 1 1 d . . .
H7 H 0.0513 0.1749 0.9471 0.094 Uiso 1 1 calc R . .
C8 C -0.1056(5) 0.2044(3) 0.9918(4) 0.0979(17) Uani 1 1 d . . .
H8 H -0.1040 0.1756 1.0518 0.117 Uiso 1 1 calc R . .
C9 C -0.1062(4) 0.2863(3) 0.8178(4) 0.0879(15) Uani 1 1 d . . .
H9 H -0.1099 0.3155 0.7583 0.106 Uiso 1 1 calc R . .
C10 C -0.1966(5) 0.2834(3) 0.8863(5) 0.1014(18) Uani 1 1 d . . .
H10 H -0.2601 0.3116 0.8703 0.122 Uiso 1 1 calc R . .
C11 C 0.3764(3) 0.09202(16) 0.9485(2) 0.0442(8) Uani 1 1 d . . .
C12 C 0.3563(3) 0.03776(17) 1.0295(2) 0.0452(8) Uani 1 1 d . . .
C13 C 0.3435(4) 0.0565(2) 1.1349(3) 0.0583(10) Uani 1 1 d . . .
H13 H 0.3429 0.1037 1.1551 0.070 Uiso 1 1 calc R . .
C14 C 0.3316(4) 0.0039(2) 1.2092(3) 0.0664(11) Uani 1 1 d . . .
H14 H 0.3227 0.0173 1.2796 0.080 Uiso 1 1 calc R . .
C15 C 0.3535(3) -0.03339(18) 1.0042(3) 0.0519(9) Uani 1 1 d . . .
H15 H 0.3602 -0.0483 0.9342 0.062 Uiso 1 1 calc R . .
C16 C 0.3406(4) -0.0818(2) 1.0851(3) 0.0600(10) Uani 1 1 d . . .
H16 H 0.3379 -0.1294 1.0671 0.072 Uiso 1 1 calc R . .
N111 N 0.4510(3) 0.91022(16) 0.6611(2) 0.0597(9) Uani 1 1 d . . .
O111 O 0.4610(3) 0.95626(14) 0.5925(2) 0.0807(10) Uani 1 1 d . . .
O222 O 0.5164(3) 0.85834(15) 0.6597(2) 0.0825(10) Uani 1 1 d . . .
O333 O 0.3799(3) 0.9143(2) 0.7286(3) 0.1069(13) Uani 1 1 d . . .
O101 O 1.0404(6) 0.0313(4) 0.6872(7) 0.215(3) Uani 1 1 d U . .
C111 C 0.9308(12) 0.1039(8) 0.5787(15) 0.241(6) Uani 1 1 d U . .
C333 C 1.047(3) -0.0065(11) 0.8670(17) 0.345(10) Uani 1 1 d U . .
C222 C 0.9266(10) 0.0657(8) 0.6691(12) 0.210(5) Uani 1 1 d U . .
C444 C 1.039(3) -0.0385(10) 0.7825(18) 0.400(14) Uani 1 1 d U . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co01 N10 1.919(2) . ?
Co01 N5 1.919(3) . ?
Co01 N4 1.953(3) . ?
Co01 N3 1.953(3) . ?
Co01 N1 1.955(3) . ?
Co01 N2 1.956(3) . ?
N1 C1 1.479(4) . ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?
N2 C2 1.482(5) . ?
N2 H2A 0.9000 . ?
N2 H2B 0.9000 . ?
N3 C3 1.477(5) . ?
N3 H3A 0.9000 . ?
N3 H3B 0.9000 . ?
N4 C4 1.474(4) . ?
N4 H4A 0.9000 . ?
N4 H4B 0.9000 . ?
N5 N6 1.314(4) . ?
N5 N8 1.328(4) . ?
N6 N7 1.340(4) . ?
N7 C5 1.333(5) . ?
N8 C5 1.324(5) . ?
N9 C10 1.320(7) . ?
N9 C8 1.331(7) . ?
N10 N11 1.313(4) . ?
N10 N13 1.335(3) . ?
N11 N12 1.337(4) . ?
N12 C11 1.336(4) . ?
N13 C11 1.331(4) . ?
N14 C14 1.327(5) . ?
N14 C16 1.330(5) . ?
C1 C2 1.507(5) . ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C2 H2C 0.9700 . ?
C2 H2D 0.9700 . ?
C3 C4 1.491(5) . ?
C3 H3C 0.9700 . ?
C3 H3D 0.9700 . ?
C4 H4C 0.9700 . ?
C4 H4D 0.9700 . ?
C5 C6 1.470(5) . ?
C6 C7 1.375(6) . ?
C6 C9 1.375(6) . ?
C7 C8 1.382(6) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.391(7) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.472(4) . ?
C12 C13 1.385(5) . ?
C12 C15 1.385(5) . ?
C13 C14 1.376(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.382(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
N111 O333 1.216(4) . ?
N111 O111 1.235(4) . ?
N111 O222 1.246(4) . ?
O101 C222 1.490(14) . ?
O101 C444 1.79(2) . ?
C111 C222 1.349(17) . ?
C333 C444 1.22(2) . ?

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
N10 Co01 N5 87.98(12) . . ?
N10 Co01 N4 91.38(11) . . ?
N5 Co01 N4 176.13(12) . . ?
N10 Co01 N3 91.31(11) . . ?
N5 Co01 N3 91.17(12) . . ?
N4 Co01 N3 85.02(12) . . ?
N10 Co01 N1 90.51(11) . . ?
N5 Co01 N1 91.41(13) . . ?
N4 Co01 N1 92.42(12) . . ?
N3 Co01 N1 176.90(11) . . ?
N10 Co01 N2 174.76(13) . . ?
N5 Co01 N2 88.66(12) . . ?
N4 Co01 N2 92.24(12) . . ?
N3 Co01 N2 92.77(12) . . ?
N1 Co01 N2 85.56(12) . . ?
C1 N1 Co01 110.2(2) . . ?
C1 N1 H1A 109.6 . . ?
Co01 N1 H1A 109.6 . . ?
C1 N1 H1B 109.6 . . ?
Co01 N1 H1B 109.6 . . ?
H1A N1 H1B 108.1 . . ?
C2 N2 Co01 109.1(2) . . ?
C2 N2 H2A 109.9 . . ?
Co01 N2 H2A 109.9 . . ?
C2 N2 H2B 109.9 . . ?
Co01 N2 H2B 109.9 . . ?
H2A N2 H2B 108.3 . . ?
C3 N3 Co01 110.0(2) . . ?
C3 N3 H3A 109.7 . . ?
Co01 N3 H3A 109.7 . . ?
C3 N3 H3B 109.7 . . ?
Co01 N3 H3B 109.7 . . ?
H3A N3 H3B 108.2 . . ?
C4 N4 Co01 110.1(2) . . ?
C4 N4 H4A 109.6 . . ?
Co01 N4 H4A 109.6 . . ?
C4 N4 H4B 109.6 . . ?
Co01 N4 H4B 109.6 . . ?
H4A N4 H4B 108.2 . . ?
N6 N5 N8 111.1(3) . . ?
N6 N5 Co01 124.1(2) . . ?
N8 N5 Co01 124.7(2) . . ?
N5 N6 N7 107.9(3) . . ?
C5 N7 N6 105.1(3) . . ?
C5 N8 N5 104.0(3) . . ?
C10 N9 C8 115.4(4) . . ?
N11 N10 N13 112.0(2) . . ?
N11 N10 Co01 124.2(2) . . ?
N13 N10 Co01 122.4(2) . . ?
N10 N11 N12 107.3(2) . . ?
C11 N12 N11 105.6(2) . . ?
C11 N13 N10 103.0(2) . . ?
C14 N14 C16 116.2(3) . . ?
N1 C1 C2 107.2(3) . . ?
N1 C1 H1C 110.3 . . ?
C2 C1 H1C 110.3 . . ?
N1 C1 H1D 110.3 . . ?
C2 C1 H1D 110.3 . . ?
H1C C1 H1D 108.5 . . ?
N2 C2 C1 107.0(3) . . ?
N2 C2 H2C 110.3 . . ?
C1 C2 H2C 110.3 . . ?
N2 C2 H2D 110.3 . . ?
C1 C2 H2D 110.3 . . ?
H2C C2 H2D 108.6 . . ?
N3 C3 C4 107.7(3) . . ?
N3 C3 H3C 110.2 . . ?
C4 C3 H3C 110.2 . . ?
N3 C3 H3D 110.2 . . ?
C4 C3 H3D 110.2 . . ?
H3C C3 H3D 108.5 . . ?
N4 C4 C3 106.9(3) . . ?
N4 C4 H4C 110.3 . . ?
C3 C4 H4C 110.3 . . ?
N4 C4 H4D 110.3 . . ?
C3 C4 H4D 110.3 . . ?
H4C C4 H4D 108.6 . . ?
N8 C5 N7 111.9(3) . . ?
N8 C5 C6 123.8(3) . . ?
N7 C5 C6 124.3(3) . . ?
C7 C6 C9 117.4(4) . . ?
C7 C6 C5 121.3(4) . . ?
C9 C6 C5 121.3(4) . . ?
C6 C7 C8 119.1(5) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
N9 C8 C7 124.6(5) . . ?
N9 C8 H8 117.7 . . ?
C7 C8 H8 117.7 . . ?
C6 C9 C10 119.0(5) . . ?
C6 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
N9 C10 C9 124.5(5) . . ?
N9 C10 H10 117.7 . . ?
C9 C10 H10 117.7 . . ?
N13 C11 N12 112.1(3) . . ?
N13 C11 C12 123.7(3) . . ?
N12 C11 C12 124.2(3) . . ?
C13 C12 C15 117.7(3) . . ?
C13 C12 C11 120.6(3) . . ?
C15 C12 C11 121.6(3) . . ?
C14 C13 C12 118.8(3) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
N14 C14 C13 124.4(4) . . ?
N14 C14 H14 117.8 . . ?
C13 C14 H14 117.8 . . ?
C16 C15 C12 118.7(3) . . ?
C16 C15 H15 120.7 . . ?
C12 C15 H15 120.7 . . ?
N14 C16 C15 124.2(4) . . ?
N14 C16 H16 117.9 . . ?
C15 C16 H16 117.9 . . ?
O333 N111 O111 122.0(4) . . ?
O333 N111 O222 119.8(4) . . ?
O111 N111 O222 118.2(3) . . ?
C222 O101 C444 113.0(14) . . ?
C111 C222 O101 107.4(11) . . ?
C333 C444 O101 102.2(19) . . ?

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
N10 Co01 N1 C1 -172.3(3) . . . . ?
N5 Co01 N1 C1 99.7(3) . . . . ?
N4 Co01 N1 C1 -80.9(3) . . . . ?
N3 Co01 N1 C1 -46(2) . . . . ?
N2 Co01 N1 C1 11.2(3) . . . . ?
N10 Co01 N2 C2 -24.7(14) . . . . ?
N5 Co01 N2 C2 -74.7(3) . . . . ?
N4 Co01 N2 C2 109.0(3) . . . . ?
N3 Co01 N2 C2 -165.8(2) . . . . ?
N1 Co01 N2 C2 16.8(2) . . . . ?
N10 Co01 N3 C3 78.8(2) . . . . ?
N5 Co01 N3 C3 166.8(2) . . . . ?
N4 Co01 N3 C3 -12.5(2) . . . . ?
N1 Co01 N3 C3 -47(2) . . . . ?
N2 Co01 N3 C3 -104.5(2) . . . . ?
N10 Co01 N4 C4 -106.2(2) . . . . ?
N5 Co01 N4 C4 -25.7(17) . . . . ?
N3 Co01 N4 C4 -15.0(2) . . . . ?
N1 Co01 N4 C4 163.3(2) . . . . ?
N2 Co01 N4 C4 77.6(2) . . . . ?
N10 Co01 N5 N6 138.2(3) . . . . ?
N4 Co01 N5 N6 57.6(17) . . . . ?
N3 Co01 N5 N6 47.0(3) . . . . ?
N1 Co01 N5 N6 -131.3(3) . . . . ?
N2 Co01 N5 N6 -45.8(3) . . . . ?
N10 Co01 N5 N8 -38.0(3) . . . . ?
N4 Co01 N5 N8 -118.7(16) . . . . ?
N3 Co01 N5 N8 -129.3(3) . . . . ?
N1 Co01 N5 N8 52.4(3) . . . . ?
N2 Co01 N5 N8 138.0(3) . . . . ?
N8 N5 N6 N7 -1.4(5) . . . . ?
Co01 N5 N6 N7 -178.1(3) . . . . ?
N5 N6 N7 C5 0.7(5) . . . . ?
N6 N5 N8 C5 1.5(4) . . . . ?
Co01 N5 N8 C5 178.2(3) . . . . ?
N5 Co01 N10 N11 -64.1(3) . . . . ?
N4 Co01 N10 N11 112.1(3) . . . . ?
N3 Co01 N10 N11 27.0(3) . . . . ?
N1 Co01 N10 N11 -155.5(3) . . . . ?
N2 Co01 N10 N11 -114.2(12) . . . . ?
N5 Co01 N10 N13 101.4(3) . . . . ?
N4 Co01 N10 N13 -82.4(3) . . . . ?
N3 Co01 N10 N13 -167.5(3) . . . . ?
N1 Co01 N10 N13 10.0(3) . . . . ?
N2 Co01 N10 N13 51.3(13) . . . . ?
N13 N10 N11 N12 -0.5(4) . . . . ?
Co01 N10 N11 N12 166.3(2) . . . . ?
N10 N11 N12 C11 0.2(4) . . . . ?
N11 N10 N13 C11 0.6(4) . . . . ?
Co01 N10 N13 C11 -166.5(2) . . . . ?
Co01 N1 C1 C2 -36.1(4) . . . . ?
Co01 N2 C2 C1 -40.5(4) . . . . ?
N1 C1 C2 N2 49.7(4) . . . . ?
Co01 N3 C3 C4 37.0(3) . . . . ?
Co01 N4 C4 C3 38.7(4) . . . . ?
N3 C3 C4 N4 -48.8(4) . . . . ?
N5 N8 C5 N7 -1.1(5) . . . . ?
N5 N8 C5 C6 179.1(4) . . . . ?
N6 N7 C5 N8 0.3(5) . . . . ?
N6 N7 C5 C6 -179.9(4) . . . . ?
N8 C5 C6 C7 18.6(7) . . . . ?
N7 C5 C6 C7 -161.2(4) . . . . ?
N8 C5 C6 C9 -160.5(5) . . . . ?
N7 C5 C6 C9 19.7(7) . . . . ?
C9 C6 C7 C8 0.4(8) . . . . ?
C5 C6 C7 C8 -178.8(5) . . . . ?
C10 N9 C8 C7 0.1(10) . . . . ?
C6 C7 C8 N9 -0.3(9) . . . . ?
C7 C6 C9 C10 -0.3(8) . . . . ?
C5 C6 C9 C10 178.9(5) . . . . ?
C8 N9 C10 C9 0.1(10) . . . . ?
C6 C9 C10 N9 0.0(10) . . . . ?
N10 N13 C11 N12 -0.4(4) . . . . ?
N10 N13 C11 C12 -179.4(3) . . . . ?
N11 N12 C11 N13 0.2(4) . . . . ?
N11 N12 C11 C12 179.1(3) . . . . ?
N13 C11 C12 C13 -167.7(4) . . . . ?
N12 C11 C12 C13 13.4(6) . . . . ?
N13 C11 C12 C15 14.6(6) . . . . ?
N12 C11 C12 C15 -164.3(4) . . . . ?
C15 C12 C13 C14 1.6(6) . . . . ?
C11 C12 C13 C14 -176.2(4) . . . . ?
C16 N14 C14 C13 -2.3(7) . . . . ?
C12 C13 C14 N14 0.2(7) . . . . ?
C13 C12 C15 C16 -1.3(6) . . . . ?
C11 C12 C15 C16 176.4(4) . . . . ?
C14 N14 C16 C15 2.5(7) . . . . ?
C12 C15 C16 N14 -0.8(7) . . . . ?
C444 O101 C222 C111 -164.7(14) . . . . ?
C222 O101 C444 C333 -82(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.059
_database_code_depnum_ccdc_archive 'CCDC 933044'
#######################################################################
#
#                 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_sm052
#TrackingRef 'sm052.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H31 Br2 Co N14 O4'
_chemical_formula_weight         762.35

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           Triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   8.5104(7)
_cell_length_b                   12.417(2)
_cell_length_c                   16.104(2)
_cell_angle_alpha                109.442(14)
_cell_angle_beta                 100.647(9)
_cell_angle_gamma                95.584(10)
_cell_volume                     1553.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2663
_cell_measurement_theta_min      3.0439
_cell_measurement_theta_max      32.2901

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    3.176
_exptl_absorpt_correction_T_min  0.3782
_exptl_absorpt_correction_T_max  0.4594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10996
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_sigmaI/netI    0.0690
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5454
_reflns_number_gt                3659
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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)+(0.1042P)²+3.4398P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5454
_refine_ls_number_parameters     384
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1017
_refine_ls_R_factor_gt           0.0692
_refine_ls_wR_factor_ref         0.2293
_refine_ls_wR_factor_gt          0.1984
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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 0.0000 0.0000 0.0000 0.0447(3) Uani 1 2 d S . .
Co2 Co 0.5000 0.5000 0.0000 0.0422(3) Uani 1 2 d S . .
Br1 Br -0.02113(19) 0.71853(12) 0.49560(8) 0.1314(5) Uani 1 1 d . . .
Br2 Br 0.50307(19) 0.26668(18) 0.52377(10) 0.1553(7) Uani 1 1 d . . .
N1 N 0.1182(7) 0.3443(5) 0.0961(4) 0.0579(14) Uani 1 1 d . . .
N2 N 0.1108(7) 0.2385(5) 0.0356(4) 0.0578(14) Uani 1 1 d . . .
N3 N 0.0364(6) 0.1639(5) 0.0625(4) 0.0489(12) Uani 1 1 d . . .
N4 N -0.0067(6) 0.2163(5) 0.1406(4) 0.0535(13) Uani 1 1 d . . .
N5 N 0.2273(6) 0.0051(5) -0.0053(4) 0.0519(13) Uani 1 1 d . . .
H5A H 0.2351 -0.0447 -0.0591 0.062 Uiso 1 1 calc R . .
H5B H 0.2706 0.0769 0.0001 0.062 Uiso 1 1 calc R . .
N6 N 0.0677(6) -0.0207(5) 0.1152(4) 0.0531(13) Uani 1 1 d . . .
H6A H 0.0151 0.0200 0.1555 0.064 Uiso 1 1 calc R . .
H6B H 0.0445 -0.0961 0.1078 0.064 Uiso 1 1 calc R . .
N7 N 0.3988(6) 0.3753(4) -0.1138(3) 0.0486(12) Uani 1 1 d . . .
H7A H 0.4128 0.3974 -0.1602 0.058 Uiso 1 1 calc R . .
H7B H 0.4460 0.3126 -0.1176 0.058 Uiso 1 1 calc R . .
N8 N 0.2803(6) 0.5109(4) 0.0176(4) 0.0499(13) Uani 1 1 d . . .
H8A H 0.2597 0.4759 0.0562 0.060 Uiso 1 1 calc R . .
H8B H 0.2694 0.5857 0.0409 0.060 Uiso 1 1 calc R . .
N9 N 0.5170(6) 0.3915(4) 0.0608(3) 0.0473(12) Uani 1 1 d . . .
N10 N 0.5256(7) 0.2814(5) 0.0234(4) 0.0631(15) Uani 1 1 d . . .
N11 N 0.5311(8) 0.2339(5) 0.0873(4) 0.0642(16) Uani 1 1 d . . .
N12 N 0.5138(6) 0.4193(5) 0.1474(4) 0.0502(13) Uani 1 1 d . . .
C1 C 0.0478(7) 0.3268(6) 0.1591(4) 0.0501(15) Uani 1 1 d . . .
C2 C 0.0305(8) 0.4205(6) 0.2396(5) 0.0556(16) Uani 1 1 d . . .
C3 C -0.0533(10) 0.3988(8) 0.2991(6) 0.078(2) Uani 1 1 d . . .
H3 H -0.0988 0.3227 0.2880 0.094 Uiso 1 1 calc R . .
C4 C -0.0725(11) 0.4846(9) 0.3740(6) 0.087(3) Uani 1 1 d . . .
H4 H -0.1316 0.4677 0.4126 0.104 Uiso 1 1 calc R . .
C5 C -0.0013(11) 0.5979(8) 0.3909(6) 0.081(2) Uani 1 1 d . . .
C6 C 0.0837(12) 0.6231(8) 0.3345(6) 0.084(2) Uani 1 1 d . . .
H6 H 0.1303 0.6992 0.3467 0.101 Uiso 1 1 calc R . .
C7 C 0.1010(10) 0.5347(7) 0.2584(5) 0.069(2) Uani 1 1 d . . .
H7 H 0.1598 0.5518 0.2198 0.082 Uiso 1 1 calc R . .
C8 C 0.3183(8) -0.0263(7) 0.0686(5) 0.0613(18) Uani 1 1 d . . .
H8A H 0.4323 0.0075 0.0839 0.074 Uiso 1 1 calc R . .
H8B H 0.3091 -0.1098 0.0505 0.074 Uiso 1 1 calc R . .
C9 C 0.2442(8) 0.0208(6) 0.1478(5) 0.0589(17) Uani 1 1 d . . .
H9A H 0.2879 -0.0066 0.1957 0.071 Uiso 1 1 calc R . .
H9B H 0.2672 0.1048 0.1713 0.071 Uiso 1 1 calc R . .
C10 C 0.5238(8) 0.3202(6) 0.1617(5) 0.0522(16) Uani 1 1 d . . .
C11 C 0.5191(8) 0.3070(7) 0.2483(5) 0.0583(18) Uani 1 1 d . . .
C12 C 0.4468(10) 0.3819(9) 0.3088(6) 0.078(2) Uani 1 1 d . . .
H12 H 0.4020 0.4407 0.2945 0.094 Uiso 1 1 calc R . .
C13 C 0.4412(11) 0.3690(11) 0.3916(6) 0.099(3) Uani 1 1 d . . .
H13 H 0.3933 0.4187 0.4329 0.119 Uiso 1 1 calc R . .
C14 C 0.5090(12) 0.2800(11) 0.4101(7) 0.094(3) Uani 1 1 d . . .
C15 C 0.5808(12) 0.2079(9) 0.3518(6) 0.085(3) Uani 1 1 d . . .
H15 H 0.6278 0.1503 0.3667 0.103 Uiso 1 1 calc R . .
C16 C 0.5843(9) 0.2197(7) 0.2707(5) 0.070(2) Uani 1 1 d . . .
H16 H 0.6313 0.1683 0.2300 0.083 Uiso 1 1 calc R . .
C17 C 0.2242(8) 0.3456(6) -0.1200(5) 0.0614(18) Uani 1 1 d . . .
H17A H 0.2061 0.2884 -0.0924 0.074 Uiso 1 1 calc R . .
H17B H 0.1656 0.3132 -0.1830 0.074 Uiso 1 1 calc R . .
C18 C 0.1656(8) 0.4526(7) -0.0723(5) 0.0631(19) Uani 1 1 d . . .
H18A H 0.0571 0.4335 -0.0648 0.076 Uiso 1 1 calc R . .
H18B H 0.1622 0.5033 -0.1070 0.076 Uiso 1 1 calc R . .
C111 C 0.9643(15) 0.9757(13) 0.3427(8) 0.136(5) Uani 1 1 d . . .
H11A H 1.0164 0.9158 0.3097 0.204 Uiso 1 1 calc R . .
H11B H 0.9978 0.9899 0.4063 0.204 Uiso 1 1 calc R . .
H11C H 0.9942 1.0454 0.3317 0.204 Uiso 1 1 calc R . .
C222 C 0.7008(19) 0.8972(16) 0.3695(10) 0.172(7) Uani 1 1 d . . .
H22A H 0.5867 0.8811 0.3424 0.257 Uiso 1 1 calc R . .
H22B H 0.7217 0.9552 0.4290 0.257 Uiso 1 1 calc R . .
H22C H 0.7359 0.8276 0.3737 0.257 Uiso 1 1 calc R . .
C333 C 0.7128(12) 0.9448(9) 0.2342(6) 0.086(3) Uani 1 1 d . . .
H333 H 0.6019 0.9166 0.2158 0.104 Uiso 1 1 calc R . .
O101 N 0.7704(8) 0.9812(7) 0.1861(4) 0.0734(19) Uani 1 1 d . . .
N111 N 0.7428(9) 0.2337(6) 0.8062(6) 0.0648(18) Uani 1 1 d . . .
O111 O 0.6362(11) 0.2823(9) 0.7898(7) 0.145(3) Uani 1 1 d . . .
O222 O 0.776(2) 0.1597(10) 0.7414(9) 0.226(7) Uani 1 1 d . . .
O333 O 0.8214(13) 0.2538(8) 0.8734(10) 0.159(4) Uani 1 1 d . . .
N222 O 0.7901(11) 0.9395(7) 0.3133(5) 0.117(2) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N3 1.910(5) 2 ?
Co1 N3 1.910(5) . ?
Co1 N6 1.946(5) 2 ?
Co1 N6 1.946(5) . ?
Co1 N5 1.948(5) 2 ?
Co1 N5 1.948(5) . ?
Co2 N9 1.913(5) 2_665 ?
Co2 N9 1.913(5) . ?
Co2 N7 1.941(5) 2_665 ?
Co2 N7 1.941(5) . ?
Co2 N8 1.953(5) . ?
Co2 N8 1.953(5) 2_665 ?
Br1 C5 1.894(9) . ?
Br2 C14 1.901(9) . ?
N1 C1 1.335(8) . ?
N1 N2 1.338(8) . ?
N2 N3 1.305(7) . ?
N3 N4 1.346(7) . ?
N4 C1 1.319(8) . ?
N5 C8 1.482(8) . ?
N5 H5A 0.9000 . ?
N5 H5B 0.9000 . ?
N6 C9 1.475(8) . ?
N6 H6A 0.9000 . ?
N6 H6B 0.9000 . ?
N7 C17 1.472(8) . ?
N7 H7A 0.9000 . ?
N7 H7B 0.9000 . ?
N8 C18 1.489(9) . ?
N8 H8A 0.9000 . ?
N8 H8B 0.9000 . ?
N9 N10 1.313(7) . ?
N9 N12 1.327(7) . ?
N10 N11 1.342(8) . ?
N11 C10 1.332(9) . ?
N12 C10 1.332(8) . ?
C1 C2 1.468(9) . ?
C2 C3 1.373(10) . ?
C2 C7 1.394(10) . ?
C3 C4 1.367(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(13) . ?
C4 H4 0.9300 . ?
C5 C6 1.354(12) . ?
C6 C7 1.390(11) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.496(10) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.464(9) . ?
C11 C12 1.386(12) . ?
C11 C16 1.385(10) . ?
C12 C13 1.404(11) . ?
C12 H12 0.9300 . ?
C13 C14 1.387(15) . ?
C13 H13 0.9300 . ?
C14 C15 1.347(14) . ?
C15 C16 1.367(11) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.481(10) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C111 N222 1.446(13) . ?
C111 H11A 0.9600 . ?
C111 H11B 0.9600 . ?
C111 H11C 0.9600 . ?
C222 N222 1.471(12) . ?
C222 H22A 0.9600 . ?
C222 H22B 0.9600 . ?
C222 H22C 0.9600 . ?
C333 O101 1.172(10) . ?
C333 N222 1.348(11) . ?
C333 H333 0.9300 . ?
N111 O333 1.095(12) . ?
N111 O111 1.176(10) . ?
N111 O222 1.238(12) . ?

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
N3 Co1 N3 180.0(3) 2 . ?
N3 Co1 N6 89.5(2) 2 2 ?
N3 Co1 N6 90.5(2) . 2 ?
N3 Co1 N6 90.5(2) 2 . ?
N3 Co1 N6 89.5(2) . . ?
N6 Co1 N6 180.0(3) 2 . ?
N3 Co1 N5 90.9(2) 2 2 ?
N3 Co1 N5 89.1(2) . 2 ?
N6 Co1 N5 85.7(2) 2 2 ?
N6 Co1 N5 94.3(2) . 2 ?
N3 Co1 N5 89.1(2) 2 . ?
N3 Co1 N5 90.9(2) . . ?
N6 Co1 N5 94.3(2) 2 . ?
N6 Co1 N5 85.7(2) . . ?
N5 Co1 N5 180.0 2 . ?
N9 Co2 N9 180.0(2) 2_665 . ?
N9 Co2 N7 90.6(2) 2_665 2_665 ?
N9 Co2 N7 89.4(2) . 2_665 ?
N9 Co2 N7 89.4(2) 2_665 . ?
N9 Co2 N7 90.6(2) . . ?
N7 Co2 N7 180.000(1) 2_665 . ?
N9 Co2 N8 89.9(2) 2_665 . ?
N9 Co2 N8 90.1(2) . . ?
N7 Co2 N8 93.8(2) 2_665 . ?
N7 Co2 N8 86.2(2) . . ?
N9 Co2 N8 90.1(2) 2_665 2_665 ?
N9 Co2 N8 89.9(2) . 2_665 ?
N7 Co2 N8 86.2(2) 2_665 2_665 ?
N7 Co2 N8 93.8(2) . 2_665 ?
N8 Co2 N8 180.0(5) . 2_665 ?
C1 N1 N2 105.1(5) . . ?
N3 N2 N1 107.6(5) . . ?
N2 N3 N4 111.8(5) . . ?
N2 N3 Co1 123.7(4) . . ?
N4 N3 Co1 124.5(4) . . ?
C1 N4 N3 102.7(5) . . ?
C8 N5 Co1 110.1(4) . . ?
C8 N5 H5A 109.6 . . ?
Co1 N5 H5A 109.6 . . ?
C8 N5 H5B 109.6 . . ?
Co1 N5 H5B 109.6 . . ?
H5A N5 H5B 108.2 . . ?
C9 N6 Co1 107.7(4) . . ?
C9 N6 H6A 110.2 . . ?
Co1 N6 H6A 110.2 . . ?
C9 N6 H6B 110.2 . . ?
Co1 N6 H6B 110.2 . . ?
H6A N6 H6B 108.5 . . ?
C17 N7 Co2 110.1(4) . . ?
C17 N7 H7A 109.6 . . ?
Co2 N7 H7A 109.6 . . ?
C17 N7 H7B 109.6 . . ?
Co2 N7 H7B 109.6 . . ?
H7A N7 H7B 108.1 . . ?
C18 N8 Co2 107.7(4) . . ?
C18 N8 H8A 110.2 . . ?
Co2 N8 H8A 110.2 . . ?
C18 N8 H8B 110.2 . . ?
Co2 N8 H8B 110.2 . . ?
H8A N8 H8B 108.5 . . ?
N10 N9 N12 111.5(5) . . ?
N10 N9 Co2 125.8(4) . . ?
N12 N9 Co2 122.6(4) . . ?
N9 N10 N11 107.9(5) . . ?
C10 N11 N10 104.9(6) . . ?
C10 N12 N9 103.5(5) . . ?
N4 C1 N1 112.7(6) . . ?
N4 C1 C2 123.6(6) . . ?
N1 C1 C2 123.7(6) . . ?
C3 C2 C7 117.9(7) . . ?
C3 C2 C1 121.5(7) . . ?
C7 C2 C1 120.6(6) . . ?
C4 C3 C2 122.7(8) . . ?
C4 C3 H3 118.7 . . ?
C2 C3 H3 118.7 . . ?
C3 C4 C5 118.2(8) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C6 C5 C4 121.2(8) . . ?
C6 C5 Br1 119.4(7) . . ?
C4 C5 Br1 119.4(7) . . ?
C5 C6 C7 119.7(9) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C6 C7 C2 120.3(8) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
N5 C8 C9 106.3(5) . . ?
N5 C8 H8A 110.5 . . ?
C9 C8 H8A 110.5 . . ?
N5 C8 H8B 110.5 . . ?
C9 C8 H8B 110.5 . . ?
H8A C8 H8B 108.7 . . ?
N6 C9 C8 106.9(6) . . ?
N6 C9 H9A 110.3 . . ?
C8 C9 H9A 110.3 . . ?
N6 C9 H9B 110.3 . . ?
C8 C9 H9B 110.3 . . ?
H9A C9 H9B 108.6 . . ?
N12 C10 N11 112.3(6) . . ?
N12 C10 C11 123.6(7) . . ?
N11 C10 C11 124.1(6) . . ?
C12 C11 C16 119.1(7) . . ?
C12 C11 C10 119.8(7) . . ?
C16 C11 C10 121.1(7) . . ?
C11 C12 C13 120.0(9) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 118.1(10) . . ?
C14 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
C15 C14 C13 121.9(8) . . ?
C15 C14 Br2 120.9(8) . . ?
C13 C14 Br2 117.1(9) . . ?
C14 C15 C16 119.8(9) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C11 121.0(9) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
N7 C17 C18 108.4(6) . . ?
N7 C17 H17A 110.0 . . ?
C18 C17 H17A 110.0 . . ?
N7 C17 H17B 110.0 . . ?
C18 C17 H17B 110.0 . . ?
H17A C17 H17B 108.4 . . ?
C17 C18 N8 107.6(6) . . ?
C17 C18 H18A 110.2 . . ?
N8 C18 H18A 110.2 . . ?
C17 C18 H18B 110.2 . . ?
N8 C18 H18B 110.2 . . ?
H18A C18 H18B 108.5 . . ?
N222 C111 H11A 109.5 . . ?
N222 C111 H11B 109.5 . . ?
H11A C111 H11B 109.5 . . ?
N222 C111 H11C 109.5 . . ?
H11A C111 H11C 109.5 . . ?
H11B C111 H11C 109.5 . . ?
N222 C222 H22A 109.5 . . ?
N222 C222 H22B 109.5 . . ?
H22A C222 H22B 109.5 . . ?
N222 C222 H22C 109.5 . . ?
H22A C222 H22C 109.5 . . ?
H22B C222 H22C 109.5 . . ?
O101 C333 N222 127.0(10) . . ?
O101 C333 H333 116.5 . . ?
N222 C333 H333 116.5 . . ?
O333 N111 O111 125.1(11) . . ?
O333 N111 O222 117.5(12) . . ?
O111 N111 O222 117.1(12) . . ?
C333 N222 C111 118.9(9) . . ?
C333 N222 C222 121.2(10) . . ?
C111 N222 C222 119.8(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 N3 1.0(7) . . . . ?
N1 N2 N3 N4 -0.3(7) . . . . ?
N1 N2 N3 Co1 -178.5(4) . . . . ?
N3 Co1 N3 N2 140(11) 2 . . . ?
N6 Co1 N3 N2 -44.5(5) 2 . . . ?
N6 Co1 N3 N2 135.5(5) . . . . ?
N5 Co1 N3 N2 -130.2(5) 2 . . . ?
N5 Co1 N3 N2 49.8(5) . . . . ?
N3 Co1 N3 N4 -38(11) 2 . . . ?
N6 Co1 N3 N4 137.5(5) 2 . . . ?
N6 Co1 N3 N4 -42.5(5) . . . . ?
N5 Co1 N3 N4 51.8(5) 2 . . . ?
N5 Co1 N3 N4 -128.2(5) . . . . ?
N2 N3 N4 C1 -0.6(7) . . . . ?
Co1 N3 N4 C1 177.6(4) . . . . ?
N3 Co1 N5 C8 -82.0(5) 2 . . . ?
N3 Co1 N5 C8 98.0(5) . . . . ?
N6 Co1 N5 C8 -171.5(4) 2 . . . ?
N6 Co1 N5 C8 8.5(4) . . . . ?
N5 Co1 N5 C8 -5(10) 2 . . . ?
N3 Co1 N6 C9 109.3(4) 2 . . . ?
N3 Co1 N6 C9 -70.7(4) . . . . ?
N6 Co1 N6 C9 124(100) 2 . . . ?
N5 Co1 N6 C9 -159.8(4) 2 . . . ?
N5 Co1 N6 C9 20.2(4) . . . . ?
N9 Co2 N7 C17 -97.6(4) 2_665 . . . ?
N9 Co2 N7 C17 82.4(4) . . . . ?
N7 Co2 N7 C17 130(100) 2_665 . . . ?
N8 Co2 N7 C17 -7.7(4) . . . . ?
N8 Co2 N7 C17 172.3(4) 2_665 . . . ?
N9 Co2 N8 C18 70.7(4) 2_665 . . . ?
N9 Co2 N8 C18 -109.3(4) . . . . ?
N7 Co2 N8 C18 161.2(4) 2_665 . . . ?
N7 Co2 N8 C18 -18.8(4) . . . . ?
N8 Co2 N8 C18 -49(100) 2_665 . . . ?
N9 Co2 N9 N10 171(100) 2_665 . . . ?
N7 Co2 N9 N10 -153.7(5) 2_665 . . . ?
N7 Co2 N9 N10 26.3(5) . . . . ?
N8 Co2 N9 N10 112.5(5) . . . . ?
N8 Co2 N9 N10 -67.5(5) 2_665 . . . ?
N9 Co2 N9 N12 -6(100) 2_665 . . . ?
N7 Co2 N9 N12 29.5(4) 2_665 . . . ?
N7 Co2 N9 N12 -150.5(4) . . . . ?
N8 Co2 N9 N12 -64.3(5) . . . . ?
N8 Co2 N9 N12 115.7(5) 2_665 . . . ?
N12 N9 N10 N11 -1.0(7) . . . . ?
Co2 N9 N10 N11 -178.1(4) . . . . ?
N9 N10 N11 C10 0.6(7) . . . . ?
N10 N9 N12 C10 1.0(7) . . . . ?
Co2 N9 N12 C10 178.2(4) . . . . ?
N3 N4 C1 N1 1.2(7) . . . . ?
N3 N4 C1 C2 -179.7(6) . . . . ?
N2 N1 C1 N4 -1.4(8) . . . . ?
N2 N1 C1 C2 179.5(6) . . . . ?
N4 C1 C2 C3 -3.8(11) . . . . ?
N1 C1 C2 C3 175.2(7) . . . . ?
N4 C1 C2 C7 175.4(7) . . . . ?
N1 C1 C2 C7 -5.6(11) . . . . ?
C7 C2 C3 C4 1.4(13) . . . . ?
C1 C2 C3 C4 -179.3(8) . . . . ?
C2 C3 C4 C5 -1.2(14) . . . . ?
C3 C4 C5 C6 0.6(14) . . . . ?
C3 C4 C5 Br1 -178.6(7) . . . . ?
C4 C5 C6 C7 -0.2(14) . . . . ?
Br1 C5 C6 C7 178.9(6) . . . . ?
C5 C6 C7 C2 0.4(13) . . . . ?
C3 C2 C7 C6 -1.0(12) . . . . ?
C1 C2 C7 C6 179.8(7) . . . . ?
Co1 N5 C8 C9 -34.9(6) . . . . ?
Co1 N6 C9 C8 -44.6(6) . . . . ?
N5 C8 C9 N6 51.7(7) . . . . ?
N9 N12 C10 N11 -0.6(7) . . . . ?
N9 N12 C10 C11 -177.8(6) . . . . ?
N10 N11 C10 N12 0.1(8) . . . . ?
N10 N11 C10 C11 177.2(6) . . . . ?
N12 C10 C11 C12 23.4(10) . . . . ?
N11 C10 C11 C12 -153.4(8) . . . . ?
N12 C10 C11 C16 -157.3(7) . . . . ?
N11 C10 C11 C16 25.9(10) . . . . ?
C16 C11 C12 C13 0.3(12) . . . . ?
C10 C11 C12 C13 179.6(7) . . . . ?
C11 C12 C13 C14 -0.2(14) . . . . ?
C12 C13 C14 C15 0.9(15) . . . . ?
C12 C13 C14 Br2 178.8(7) . . . . ?
C13 C14 C15 C16 -1.7(15) . . . . ?
Br2 C14 C15 C16 -179.6(6) . . . . ?
C14 C15 C16 C11 1.8(13) . . . . ?
C12 C11 C16 C15 -1.1(11) . . . . ?
C10 C11 C16 C15 179.6(7) . . . . ?
Co2 N7 C17 C18 32.9(7) . . . . ?
N7 C17 C18 N8 -48.5(7) . . . . ?
Co2 N8 C18 C17 41.3(6) . . . . ?
O101 C333 N222 C111 -3.6(16) . . . . ?
O101 C333 N222 C222 176.7(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.635
_refine_diff_density_min         -0.726
_refine_diff_density_rms         0.092
_database_code_depnum_ccdc_archive 'CCDC 933045'
#######################################################################
#
#                 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_sm076
#TrackingRef 'sm076.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7.60 H10.40 Cl0.40 Co0.40 N4.80 O2'
_chemical_formula_weight         238.76

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           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

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

_cell_length_a                   13.0541(4)
_cell_length_b                   13.3594(7)
_cell_length_c                   14.8320(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2586.63(17)
_cell_formula_units_Z            10
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3690
_cell_measurement_theta_min      3.0037
_cell_measurement_theta_max      32.1774

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_absorpt_coefficient_mu    0.823
_exptl_absorpt_correction_T_min  0.8333
_exptl_absorpt_correction_T_max  0.9006
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18243
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.14
_diffrn_reflns_theta_max         24.99
_reflns_number_total             4554
_reflns_number_gt                4305
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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)+(0.0539P)²+2.6391P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.006(19)
_refine_ls_number_reflns         4554
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1131
_refine_ls_wR_factor_gt          0.1103
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_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 0.91173(4) 0.83183(4) 0.03754(3) 0.02879(14) Uani 1 1 d . . .
N1 N 0.9429(2) 0.7025(3) 0.0894(2) 0.0331(7) Uani 1 1 d . . .
H1A H 1.0058 0.6811 0.0692 0.040 Uiso 1 1 calc R . .
H1B H 0.9460 0.7079 0.1512 0.040 Uiso 1 1 calc R . .
N2 N 0.8051(2) 0.7613(3) -0.0320(2) 0.0325(7) Uani 1 1 d . . .
H2A H 0.7418 0.7721 -0.0064 0.039 Uiso 1 1 calc R . .
H2B H 0.8037 0.7848 -0.0903 0.039 Uiso 1 1 calc R . .
N3 N 0.8177(2) 0.8630(3) 0.1355(2) 0.0318(7) Uani 1 1 d . . .
H3A H 0.7790 0.8075 0.1492 0.038 Uiso 1 1 calc R . .
H3B H 0.8542 0.8809 0.1861 0.038 Uiso 1 1 calc R . .
N4 N 0.8757(3) 0.9639(3) -0.0108(2) 0.0372(8) Uani 1 1 d . . .
H4A H 0.9344 0.9991 -0.0236 0.045 Uiso 1 1 calc R . .
H4B H 0.8392 0.9563 -0.0634 0.045 Uiso 1 1 calc R . .
N5 N 1.0222(2) 0.8921(3) 0.1036(2) 0.0328(8) Uani 1 1 d . . .
N6 N 1.0778(2) 0.8428(3) 0.1655(2) 0.0353(7) Uani 1 1 d . . .
N7 N 1.0514(3) 0.9854(3) 0.0949(2) 0.0369(8) Uani 1 1 d . . .
N8 N 1.1293(3) 1.0001(3) 0.1521(2) 0.0374(8) Uani 1 1 d . . .
N9 N 1.0006(2) 0.8088(3) -0.0623(2) 0.0328(8) Uani 1 1 d . . .
N10 N 1.0931(3) 0.7677(3) -0.0600(2) 0.0357(8) Uani 1 1 d . . .
N11 N 1.1288(3) 0.7650(3) -0.1450(2) 0.0394(8) Uani 1 1 d . . .
N12 N 0.9745(2) 0.8333(3) -0.1472(2) 0.0346(7) Uani 1 1 d . . .
C1 C 0.8639(3) 0.6289(3) 0.0644(3) 0.0402(10) Uani 1 1 d . . .
H1C H 0.8052 0.6329 0.1065 0.048 Uiso 1 1 calc R . .
H1D H 0.8924 0.5603 0.0669 0.048 Uiso 1 1 calc R . .
C2 C 0.8291(3) 0.6533(4) -0.0315(3) 0.0433(10) Uani 1 1 d . . .
H2C H 0.8842 0.6382 -0.0752 0.052 Uiso 1 1 calc R . .
H2D H 0.7677 0.6136 -0.0476 0.052 Uiso 1 1 calc R . .
C3 C 0.7496(3) 0.9466(4) 0.1082(3) 0.0395(10) Uani 1 1 d . . .
H3C H 0.7200 0.9793 0.1621 0.047 Uiso 1 1 calc R . .
H3D H 0.6929 0.9212 0.0703 0.047 Uiso 1 1 calc R . .
C4 C 0.8133(3) 1.0202(4) 0.0558(3) 0.0417(10) Uani 1 1 d . . .
H4C H 0.7682 1.0686 0.0244 0.050 Uiso 1 1 calc R . .
H4D H 0.8586 1.0579 0.0972 0.050 Uiso 1 1 calc R . .
C5 C 1.1423(3) 0.9125(3) 0.1941(3) 0.0331(9) Uani 1 1 d . . .
C6 C 1.2217(3) 0.8932(4) 0.2624(3) 0.0373(10) Uani 1 1 d . . .
C7 C 1.2319(4) 0.7985(4) 0.2990(3) 0.0486(12) Uani 1 1 d . . .
H7 H 1.1876 0.7461 0.2803 0.058 Uiso 1 1 calc R . .
C8 C 1.3075(4) 0.7800(4) 0.3636(3) 0.0530(13) Uani 1 1 d . . .
H8 H 1.3160 0.7144 0.3871 0.064 Uiso 1 1 calc R . .
C9 C 1.3692(4) 0.8555(4) 0.3930(4) 0.0617(15) Uani 1 1 d . . .
H9 H 1.4188 0.8434 0.4386 0.074 Uiso 1 1 calc R . .
C10 C 1.3590(5) 0.9487(5) 0.3562(5) 0.079(2) Uani 1 1 d . . .
H10 H 1.4030 1.0008 0.3762 0.095 Uiso 1 1 calc R . .
C11 C 1.2863(4) 0.9697(4) 0.2906(4) 0.0575(14) Uani 1 1 d . . .
H11 H 1.2809 1.0349 0.2655 0.069 Uiso 1 1 calc R . .
C12 C 1.0554(3) 0.8063(3) -0.1964(3) 0.0339(9) Uani 1 1 d . . .
C13 C 1.0642(3) 0.8222(4) -0.2938(3) 0.0374(9) Uani 1 1 d . . .
C14 C 1.1373(4) 0.7693(4) -0.3429(3) 0.0462(11) Uani 1 1 d . . .
H14 H 1.1805 0.7217 -0.3143 0.055 Uiso 1 1 calc R . .
C15 C 1.1457(5) 0.7880(4) -0.4351(3) 0.0589(14) Uani 1 1 d . . .
H15 H 1.1948 0.7521 -0.4696 0.071 Uiso 1 1 calc R . .
C16 C 1.0845(5) 0.8568(4) -0.4766(3) 0.0563(13) Uani 1 1 d . . .
H16 H 1.0920 0.8691 -0.5394 0.068 Uiso 1 1 calc R . .
C17 C 1.0124(4) 0.9084(5) -0.4280(3) 0.0575(14) Uani 1 1 d . . .
H17 H 0.9687 0.9548 -0.4577 0.069 Uiso 1 1 calc R . .
C18 C 1.0028(4) 0.8932(4) -0.3358(3) 0.0506(12) Uani 1 1 d . . .
H18 H 0.9548 0.9310 -0.3017 0.061 Uiso 1 1 calc R . .
Cl1 Cl 0.84549(9) 1.02006(10) 0.34044(7) 0.0473(3) Uani 1 1 d . . .
O111 O 0.8848(3) 0.7000(2) 0.2772(2) 0.0479(8) Uani 1 1 d . . .
O222 O 0.8770(3) 1.0623(3) 0.4215(2) 0.0679(11) Uani 1 1 d . . .
O333 O 0.9169(3) 1.0187(4) 0.2720(3) 0.0901(15) Uani 1 1 d . . .
O444 O 0.7584(5) 1.0814(7) 0.3136(4) 0.141(3) Uani 1 1 d . . .
C111 C 0.9483(6) 0.7390(6) 0.3505(5) 0.088(2) Uani 1 1 d . . .
O555 O 0.7976(7) 0.9305(5) 0.3511(4) 0.168(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N9 1.907(3) . ?
Co1 N5 1.921(3) . ?
Co1 N1 1.935(4) . ?
Co1 N3 1.947(3) . ?
Co1 N4 1.961(4) . ?
Co1 N2 1.972(3) . ?
N1 C1 1.472(5) . ?
N1 H1A 0.9200 . ?
N1 H1B 0.9200 . ?
N2 C2 1.476(6) . ?
N2 H2A 0.9200 . ?
N2 H2B 0.9200 . ?
N3 C3 1.484(6) . ?
N3 H3A 0.9200 . ?
N3 H3B 0.9200 . ?
N4 C4 1.486(5) . ?
N4 H4A 0.9200 . ?
N4 H4B 0.9200 . ?
N5 N7 1.309(5) . ?
N5 N6 1.343(5) . ?
N6 C5 1.326(5) . ?
N7 N8 1.337(5) . ?
N8 C5 1.337(6) . ?
N9 N10 1.327(4) . ?
N9 N12 1.345(4) . ?
N10 N11 1.345(4) . ?
N11 C12 1.342(5) . ?
N12 C12 1.334(5) . ?
C1 C2 1.528(6) . ?
C1 H1C 0.9900 . ?
C1 H1D 0.9900 . ?
C2 H2C 0.9900 . ?
C2 H2D 0.9900 . ?
C3 C4 1.503(6) . ?
C3 H3C 0.9900 . ?
C3 H3D 0.9900 . ?
C4 H4C 0.9900 . ?
C4 H4D 0.9900 . ?
C5 C6 1.471(6) . ?
C6 C7 1.383(7) . ?
C6 C11 1.389(7) . ?
C7 C8 1.397(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.362(8) . ?
C8 H8 0.9500 . ?
C9 C10 1.366(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(7) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.465(5) . ?
C13 C18 1.390(6) . ?
C13 C14 1.393(6) . ?
C14 C15 1.394(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.365(8) . ?
C15 H15 0.9500 . ?
C16 C17 1.372(7) . ?
C16 H16 0.9500 . ?
C17 C18 1.389(6) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
Cl1 O555 1.359(6) . ?
Cl1 O333 1.378(4) . ?
Cl1 O222 1.391(4) . ?
Cl1 O444 1.457(6) . ?
O111 C111 1.463(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
N9 Co1 N5 90.41(13) . . ?
N9 Co1 N1 92.12(14) . . ?
N5 Co1 N1 90.79(14) . . ?
N9 Co1 N3 176.31(15) . . ?
N5 Co1 N3 90.16(13) . . ?
N1 Co1 N3 91.52(14) . . ?
N9 Co1 N4 90.43(14) . . ?
N5 Co1 N4 89.39(15) . . ?
N1 Co1 N4 177.45(14) . . ?
N3 Co1 N4 85.93(14) . . ?
N9 Co1 N2 86.89(13) . . ?
N5 Co1 N2 175.70(14) . . ?
N1 Co1 N2 85.96(14) . . ?
N3 Co1 N2 92.74(14) . . ?
N4 Co1 N2 93.98(14) . . ?
C1 N1 Co1 110.4(3) . . ?
C1 N1 H1A 109.6 . . ?
Co1 N1 H1A 109.6 . . ?
C1 N1 H1B 109.6 . . ?
Co1 N1 H1B 109.6 . . ?
H1A N1 H1B 108.1 . . ?
C2 N2 Co1 108.3(2) . . ?
C2 N2 H2A 110.0 . . ?
Co1 N2 H2A 110.0 . . ?
C2 N2 H2B 110.0 . . ?
Co1 N2 H2B 110.0 . . ?
H2A N2 H2B 108.4 . . ?
C3 N3 Co1 109.5(2) . . ?
C3 N3 H3A 109.8 . . ?
Co1 N3 H3A 109.8 . . ?
C3 N3 H3B 109.8 . . ?
Co1 N3 H3B 109.8 . . ?
H3A N3 H3B 108.2 . . ?
C4 N4 Co1 110.2(3) . . ?
C4 N4 H4A 109.6 . . ?
Co1 N4 H4A 109.6 . . ?
C4 N4 H4B 109.6 . . ?
Co1 N4 H4B 109.6 . . ?
H4A N4 H4B 108.1 . . ?
N7 N5 N6 112.2(3) . . ?
N7 N5 Co1 124.6(3) . . ?
N6 N5 Co1 123.2(3) . . ?
C5 N6 N5 102.6(3) . . ?
N5 N7 N8 107.4(3) . . ?
N7 N8 C5 105.3(3) . . ?
N10 N9 N12 110.9(3) . . ?
N10 N9 Co1 126.9(2) . . ?
N12 N9 Co1 122.3(2) . . ?
N9 N10 N11 107.5(3) . . ?
C12 N11 N10 105.9(3) . . ?
C12 N12 N9 104.2(3) . . ?
N1 C1 C2 107.5(3) . . ?
N1 C1 H1C 110.2 . . ?
C2 C1 H1C 110.2 . . ?
N1 C1 H1D 110.2 . . ?
C2 C1 H1D 110.2 . . ?
H1C C1 H1D 108.5 . . ?
N2 C2 C1 106.1(3) . . ?
N2 C2 H2C 110.5 . . ?
C1 C2 H2C 110.5 . . ?
N2 C2 H2D 110.5 . . ?
C1 C2 H2D 110.5 . . ?
H2C C2 H2D 108.7 . . ?
N3 C3 C4 107.6(3) . . ?
N3 C3 H3C 110.2 . . ?
C4 C3 H3C 110.2 . . ?
N3 C3 H3D 110.2 . . ?
C4 C3 H3D 110.2 . . ?
H3C C3 H3D 108.5 . . ?
N4 C4 C3 108.3(4) . . ?
N4 C4 H4C 110.0 . . ?
C3 C4 H4C 110.0 . . ?
N4 C4 H4D 110.0 . . ?
C3 C4 H4D 110.0 . . ?
H4C C4 H4D 108.4 . . ?
N6 C5 N8 112.6(4) . . ?
N6 C5 C6 123.1(4) . . ?
N8 C5 C6 124.3(4) . . ?
C7 C6 C11 119.7(4) . . ?
C7 C6 C5 119.9(4) . . ?
C11 C6 C5 120.4(4) . . ?
C6 C7 C8 120.0(5) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 120.4(5) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 119.3(5) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C9 C10 C11 122.1(5) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C10 C11 C6 118.5(5) . . ?
C10 C11 H11 120.7 . . ?
C6 C11 H11 120.7 . . ?
N12 C12 N11 111.5(3) . . ?
N12 C12 C13 124.2(4) . . ?
N11 C12 C13 124.3(4) . . ?
C18 C13 C14 120.4(4) . . ?
C18 C13 C12 119.7(4) . . ?
C14 C13 C12 119.7(4) . . ?
C13 C14 C15 118.5(5) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 H14 120.8 . . ?
C16 C15 C14 121.1(5) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C17 120.2(4) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C18 120.4(5) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C13 119.3(5) . . ?
C17 C18 H18 120.3 . . ?
C13 C18 H18 120.3 . . ?
O555 Cl1 O333 112.7(4) . . ?
O555 Cl1 O222 113.1(3) . . ?
O333 Cl1 O222 116.2(2) . . ?
O555 Cl1 O444 99.7(6) . . ?
O333 Cl1 O444 109.5(4) . . ?
O222 Cl1 O444 103.8(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
N9 Co1 N1 C1 -96.7(3) . . . . ?
N5 Co1 N1 C1 172.9(3) . . . . ?
N3 Co1 N1 C1 82.7(3) . . . . ?
N4 Co1 N1 C1 79(3) . . . . ?
N2 Co1 N1 C1 -9.9(3) . . . . ?
N9 Co1 N2 C2 73.7(3) . . . . ?
N5 Co1 N2 C2 22(2) . . . . ?
N1 Co1 N2 C2 -18.7(3) . . . . ?
N3 Co1 N2 C2 -110.0(3) . . . . ?
N4 Co1 N2 C2 163.9(3) . . . . ?
N9 Co1 N3 C3 8(2) . . . . ?
N5 Co1 N3 C3 106.8(3) . . . . ?
N1 Co1 N3 C3 -162.4(3) . . . . ?
N4 Co1 N3 C3 17.4(3) . . . . ?
N2 Co1 N3 C3 -76.3(3) . . . . ?
N9 Co1 N4 C4 -172.1(3) . . . . ?
N5 Co1 N4 C4 -81.7(3) . . . . ?
N1 Co1 N4 C4 13(3) . . . . ?
N3 Co1 N4 C4 8.5(3) . . . . ?
N2 Co1 N4 C4 101.0(3) . . . . ?
N9 Co1 N5 N7 82.8(3) . . . . ?
N1 Co1 N5 N7 174.9(3) . . . . ?
N3 Co1 N5 N7 -93.6(3) . . . . ?
N4 Co1 N5 N7 -7.6(3) . . . . ?
N2 Co1 N5 N7 134.0(19) . . . . ?
N9 Co1 N5 N6 -98.2(3) . . . . ?
N1 Co1 N5 N6 -6.1(3) . . . . ?
N3 Co1 N5 N6 85.4(3) . . . . ?
N4 Co1 N5 N6 171.4(3) . . . . ?
N2 Co1 N5 N6 -47(2) . . . . ?
N7 N5 N6 C5 0.3(4) . . . . ?
Co1 N5 N6 C5 -178.8(2) . . . . ?
N6 N5 N7 N8 0.3(4) . . . . ?
Co1 N5 N7 N8 179.4(2) . . . . ?
N5 N7 N8 C5 -0.8(4) . . . . ?
N5 Co1 N9 N10 48.7(4) . . . . ?
N1 Co1 N9 N10 -42.1(3) . . . . ?
N3 Co1 N9 N10 148(2) . . . . ?
N4 Co1 N9 N10 138.1(3) . . . . ?
N2 Co1 N9 N10 -127.9(3) . . . . ?
N5 Co1 N9 N12 -131.6(3) . . . . ?
N1 Co1 N9 N12 137.6(3) . . . . ?
N3 Co1 N9 N12 -33(2) . . . . ?
N4 Co1 N9 N12 -42.2(3) . . . . ?
N2 Co1 N9 N12 51.7(3) . . . . ?
N12 N9 N10 N11 0.0(5) . . . . ?
Co1 N9 N10 N11 179.7(3) . . . . ?
N9 N10 N11 C12 0.5(5) . . . . ?
N10 N9 N12 C12 -0.6(5) . . . . ?
Co1 N9 N12 C12 179.7(3) . . . . ?
Co1 N1 C1 C2 35.4(4) . . . . ?
Co1 N2 C2 C1 41.7(4) . . . . ?
N1 C1 C2 N2 -50.3(4) . . . . ?
Co1 N3 C3 C4 -39.3(4) . . . . ?
Co1 N4 C4 C3 -32.3(4) . . . . ?
N3 C3 C4 N4 46.4(4) . . . . ?
N5 N6 C5 N8 -0.8(4) . . . . ?
N5 N6 C5 C6 -178.7(3) . . . . ?
N7 N8 C5 N6 1.0(4) . . . . ?
N7 N8 C5 C6 178.9(4) . . . . ?
N6 C5 C6 C7 0.7(6) . . . . ?
N8 C5 C6 C7 -177.0(4) . . . . ?
N6 C5 C6 C11 -179.2(4) . . . . ?
N8 C5 C6 C11 3.2(6) . . . . ?
C11 C6 C7 C8 -0.5(7) . . . . ?
C5 C6 C7 C8 179.7(4) . . . . ?
C6 C7 C8 C9 2.2(8) . . . . ?
C7 C8 C9 C10 -2.5(9) . . . . ?
C8 C9 C10 C11 1.1(11) . . . . ?
C9 C10 C11 C6 0.6(11) . . . . ?
C7 C6 C11 C10 -0.9(8) . . . . ?
C5 C6 C11 C10 178.9(5) . . . . ?
N9 N12 C12 N11 0.9(5) . . . . ?
N9 N12 C12 C13 -177.5(4) . . . . ?
N10 N11 C12 N12 -0.9(5) . . . . ?
N10 N11 C12 C13 177.5(4) . . . . ?
N12 C12 C13 C18 19.9(7) . . . . ?
N11 C12 C13 C18 -158.4(5) . . . . ?
N12 C12 C13 C14 -163.1(4) . . . . ?
N11 C12 C13 C14 18.6(7) . . . . ?
C18 C13 C14 C15 -1.3(8) . . . . ?
C12 C13 C14 C15 -178.3(5) . . . . ?
C13 C14 C15 C16 0.5(9) . . . . ?
C14 C15 C16 C17 -0.8(9) . . . . ?
C15 C16 C17 C18 1.8(9) . . . . ?
C16 C17 C18 C13 -2.6(9) . . . . ?
C14 C13 C18 C17 2.4(8) . . . . ?
C12 C13 C18 C17 179.4(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.061
_database_code_depnum_ccdc_archive 'CCDC 933046'
#######################################################################
#
#                 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_5
_audit_creation_date             2014-04-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_chemical_formula_moiety         '2(C16 H24 Co N14), 2(Cl O4), H2 O'
_chemical_formula_sum            'C32 H50 Cl2 Co2 N28 O9'
_chemical_formula_weight         1159.76
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Co 0.35655 0.96576 12.28410 7.34090 4.00340 2.34880 4.27910 0.27840 13.53590
71.16920 1.01180005074
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   11.6499(7)
_cell_length_b                   16.1363(13)
_cell_length_c                   13.5916(11)
_cell_angle_alpha                90
_cell_angle_beta                 95.163(6)
_cell_angle_gamma                90
_cell_volume                     2544.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_exptl_absorpt_coefficient_mu    0.834
_exptl_absorpt_correction_T_min  0.810
_exptl_absorpt_correction_T_max  0.861
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_F_000             1196.0
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_diffrn_reflns_av_R_equivalents  0.0781
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24083
_diffrn_reflns_theta_full        25.0000
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.94
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 0.9987
_diffrn_measured_fraction_theta_max 0.9987
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                3359
_reflns_number_total             4477
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
'L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation (2013)'
_refine_diff_density_max         0.8833
_refine_diff_density_min         -0.8920
_refine_diff_density_rms         0.1182
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             6.9305
_refine_ls_goodness_of_fit_ref   1.0861
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    43
_refine_ls_number_parameters     336
_refine_ls_number_reflns         4471
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0913
_refine_ls_R_factor_gt           0.0685
_refine_ls_restrained_S_all      1.0861
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0940P)²+4.3789P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2056
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Others
 Fixed Sof: O101(0.5) H10a(0.5) H10b(0.5)
3.a Free rotating group:
 O101(H10a,H10b)
3.b Secondary CH2 refined with riding coordinates:
 N1(H1a,H1b), N2(H2a,H2b), N3(H3a,H3b), N4(H4a,H4b), C1(H1c,H1d), C2(H2c,H2d),
 C3(H3c,H3d), C4(H4c,H4d)
3.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C15(H15), C16(H16)
;
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_refinement_flags_posn
Co1 Co 0.56866(5) 0.10810(4) 0.26944(5) 0.0364(2) Uani 1.000000 .
N1 N 0.4872(4) 0.0032(3) 0.2785(3) 0.0466(10) Uani 1.000000 .
H1a H 0.4552(4) 0.0002(3) 0.3379(3) 0.0559(12) Uiso 1.000000 R
H1b H 0.4288(4) -0.0004(3) 0.2285(3) 0.0559(12) Uiso 1.000000 R
N2 N 0.6925(3) 0.0418(3) 0.2214(3) 0.0438(10) Uani 1.000000 .
H2a H 0.7182(3) 0.0666(3) 0.1665(3) 0.0526(12) Uiso 1.000000 R
H2b H 0.7533(3) 0.0387(3) 0.2693(3) 0.0526(12) Uiso 1.000000 R
N3 N 0.6519(3) 0.2116(3) 0.2593(3) 0.0435(10) Uani 1.000000 .
H3a H 0.6271(3) 0.2491(3) 0.3037(3) 0.0522(12) Uiso 1.000000 R
H3b H 0.7293(3) 0.2025(3) 0.2753(3) 0.0522(12) Uiso 1.000000 R
N4 N 0.5025(4) 0.1309(3) 0.1345(3) 0.0493(11) Uani 1.000000 .
H4a H 0.5392(4) 0.0995(3) 0.0903(3) 0.0592(13) Uiso 1.000000 R
H4b H 0.4255(4) 0.1174(3) 0.1282(3) 0.0592(13) Uiso 1.000000 R
N5 N 0.6375(3) 0.0940(3) 0.4016(3) 0.0395(9) Uani 1.000000 .
N6 N 0.5823(4) 0.0730(3) 0.4779(3) 0.0510(11) Uani 1.000000 .
N7 N 0.6617(4) 0.0626(3) 0.5551(3) 0.0553(12) Uani 1.000000 .
N8 N 0.7517(4) 0.0987(3) 0.4244(3) 0.0496(11) Uani 1.000000 .
N9 N 0.4401(3) 0.1657(3) 0.3129(3) 0.0404(9) Uani 1.000000 .
N10 N 0.4437(4) 0.2308(3) 0.3720(4) 0.0549(12) Uani 1.000000 .
N11 N 0.3347(4) 0.2561(3) 0.3787(4) 0.0641(14) Uani 1.000000 .
N12 N 0.3319(3) 0.1482(3) 0.2772(4) 0.0529(12) Uani 1.000000 .
N13 N 1.0908(6) 0.0618(5) 0.6853(6) 0.103(2) Uani 1.000000 .
N14 N -0.0947(5) 0.2189(5) 0.2631(8) 0.105(3) Uani 1.000000 .
C1 C 0.5695(5) -0.0657(4) 0.2706(5) 0.0619(16) Uani 1.000000 .
H1c H 0.6135(5) -0.0755(4) 0.3354(5) 0.0743(19) Uiso 1.000000 R
H1d H 0.5274(5) -0.1171(4) 0.2505(5) 0.0743(19) Uiso 1.000000 R
C2 C 0.6492(5) -0.0429(3) 0.1958(4) 0.0543(14) Uani 1.000000 .
H2c H 0.6081(5) -0.0435(3) 0.1288(4) 0.0651(17) Uiso 1.000000 R
H2d H 0.7141(5) -0.0827(3) 0.1974(4) 0.0651(17) Uiso 1.000000 R
C3 C 0.6344(5) 0.2465(4) 0.1591(5) 0.0616(16) Uani 1.000000 .
H3c H 0.6392(5) 0.3077(4) 0.1621(5) 0.0740(19) Uiso 1.000000 R
H3d H 0.6949(5) 0.2260(4) 0.1185(5) 0.0740(19) Uiso 1.000000 R
C4 C 0.5173(5) 0.2204(4) 0.1135(4) 0.0599(15) Uani 1.000000 .
H4c H 0.5114(5) 0.2300(4) 0.0413(4) 0.0719(18) Uiso 1.000000 R
H4d H 0.4565(5) 0.2531(4) 0.1420(4) 0.0719(18) Uiso 1.000000 R
C5 C 0.7632(5) 0.0780(3) 0.5199(4) 0.0456(12) Uani 1.000000 .
C6 C 0.8746(5) 0.0742(4) 0.5785(4) 0.0580(15) Uani 1.000000 .
C7 C 0.8860(6) 0.0447(5) 0.6733(5) 0.081(2) Uani 1.000000 .
H7 H 0.8202(6) 0.0272(5) 0.7042(5) 0.097(3) Uiso 1.000000 R
C8 C 0.9936(8) 0.0407(7) 0.7234(6) 0.108(3) Uani 1.000000 .
H8 H 0.9991(8) 0.0216(7) 0.7898(6) 0.129(4) Uiso 1.000000 R
C9 C 1.0795(7) 0.0913(7) 0.5948(8) 0.111(3) Uani 1.000000 .
H9 H 1.1471(7) 0.1082(7) 0.5660(8) 0.133(4) Uiso 1.000000 R
C10 C 0.9722(6) 0.0992(5) 0.5377(6) 0.087(2) Uani 1.000000 .
H10 H 0.9680(6) 0.1213(5) 0.4727(6) 0.105(3) Uiso 1.000000 R
C11 C 0.2695(4) 0.2048(4) 0.3196(5) 0.0552(15) Uani 1.000000 .
C12 C 0.1436(5) 0.2104(4) 0.3002(6) 0.0666(18) Uani 1.000000 .
C13 C 0.0796(6) 0.2580(5) 0.3595(7) 0.093(3) Uani 1.000000 .
H13 H 0.1155(6) 0.2889(5) 0.4133(7) 0.111(3) Uiso 1.000000 R
C14 C -0.0406(8) 0.2592(7) 0.3374(10) 0.115(4) Uani 1.000000 .
H14 H -0.0853(8) 0.2910(7) 0.3787(10) 0.138(4) Uiso 1.000000 R
C15 C -0.0315(7) 0.1779(7) 0.2064(9) 0.118(4) Uani 1.000000 .
H15 H -0.0694(7) 0.1510(7) 0.1504(9) 0.142(4) Uiso 1.000000 R
C16 C 0.0889(6) 0.1702(6) 0.2216(8) 0.102(3) Uani 1.000000 .
H16 H 0.1306(6) 0.1380(6) 0.1784(8) 0.123(4) Uiso 1.000000 R
Cl1 Cl 0.71805(16) 0.43257(14) 0.43728(13) 0.0806(6) Uani 1.000000 .
O111 O 0.7731(8) 0.4056(7) 0.5212(5) 0.185(5) Uani 1.000000 .
O222 O 0.7743(15) 0.4969(10) 0.3996(12) 0.306(9) Uani 1.000000 .
O333 O 0.6063(5) 0.4578(5) 0.4597(5) 0.129(3) Uani 1.000000 .
O444 O 0.7104(8) 0.3827(7) 0.3592(8) 0.202(5) Uani 1.000000 .
O101 O 0.265(3) 0.349(2) 0.535(3) 0.250(13) Uani 0.500000 .



loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Co1 N1 1.949(4) .
Co1 N2 1.955(4) .
Co1 N3 1.943(4) .
Co1 N4 1.959(4) .
Co1 N5 1.914(4) .
Co1 N9 1.902(4) .
N1 H1a 0.9200 .
N1 H1b 0.9200 .
N1 C1 1.478(7) .
N2 H2a 0.9200 .
N2 H2b 0.9200 .
N2 C2 1.488(7) .
N3 H3a 0.9200 .
N3 H3b 0.9200 .
N3 C3 1.470(7) .
N4 H4a 0.9200 .
N4 H4b 0.9200 .
N4 C4 1.485(7) .
N5 N6 1.312(6) .
N5 N8 1.341(6) .
N6 N7 1.346(6) .
N7 C5 1.338(7) .
N8 C5 1.336(7) .
N9 N10 1.321(6) .
N9 N12 1.340(6) .
N10 N11 1.344(6) .
N11 C11 1.341(8) .
N12 C11 1.331(7) .
N13 C8 1.331(12) .
N13 C9 1.315(12) .
N14 C14 1.313(13) .
N14 C15 1.295(13) .
C1 H1c 0.9900 .
C1 H1d 0.9900 .
C1 C2 1.484(8) .
C2 H2c 0.9900 .
C2 H2d 0.9900 .
C3 H3c 0.9900 .
C3 H3d 0.9900 .
C3 C4 1.506(8) .
C4 H4c 0.9900 .
C4 H4d 0.9900 .
C5 C6 1.463(7) .
C6 C7 1.369(9) .
C6 C10 1.369(10) .
C7 H7 0.9500 .
C7 C8 1.373(11) .
C8 H8 0.9500 .
C9 H9 0.9500 .
C9 C10 1.417(10) .
C10 H10 0.9500 .
C11 C12 1.469(7) .
C12 C13 1.381(10) .
C12 C16 1.358(11) .
C13 H13 0.9500 .
C13 C14 1.405(11) .
C14 H14 0.9500 .
C15 H15 0.9500 .
C15 C16 1.405(10) .
C16 H16 0.9500 .
Cl1 O111 1.331(7) .
Cl1 O222 1.353(10) .
Cl1 O333 1.423(6) .
Cl1 O444 1.328(8) .
O101 H10a 0.8700 .
O101 H10b 0.8700 .

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
N2 Co1 N1 85.64(17) . .
N3 Co1 N1 179.00(17) . .
N3 Co1 N2 93.36(17) . .
N4 Co1 N1 94.01(19) . .
N4 Co1 N2 91.70(18) . .
N4 Co1 N3 85.90(19) . .
N5 Co1 N1 90.12(18) . .
N5 Co1 N2 89.38(17) . .
N5 Co1 N3 89.98(18) . .
N5 Co1 N4 175.80(18) . .
N9 Co1 N1 90.21(17) . .
N9 Co1 N2 175.49(17) . .
N9 Co1 N3 90.79(17) . .
N9 Co1 N4 86.82(18) . .
N9 Co1 N5 92.40(17) . .
H1a N1 Co1 109.87(13) . .
H1b N1 Co1 109.87(13) . .
H1b N1 H1a 108.3 . .
C1 N1 Co1 109.0(3) . .
C1 N1 H1a 109.9(3) . .
C1 N1 H1b 109.9(3) . .
H2a N2 Co1 109.74(12) . .
H2b N2 Co1 109.74(13) . .
H2b N2 H2a 108.2 . .
C2 N2 Co1 109.7(3) . .
C2 N2 H2a 109.7(3) . .
C2 N2 H2b 109.7(3) . .
H3a N3 Co1 109.33(13) . .
H3b N3 Co1 109.33(12) . .
H3b N3 H3a 108.0 . .
C3 N3 Co1 111.5(4) . .
C3 N3 H3a 109.3(3) . .
C3 N3 H3b 109.3(3) . .
H4a N4 Co1 109.96(13) . .
H4b N4 Co1 109.96(13) . .
H4b N4 H4a 108.3 . .
C4 N4 Co1 108.7(3) . .
C4 N4 H4a 110.0(3) . .
C4 N4 H4b 110.0(3) . .
N6 N5 Co1 125.4(3) . .
N8 N5 Co1 122.2(3) . .
N8 N5 N6 112.3(4) . .
N7 N6 N5 107.3(4) . .
C5 N7 N6 105.3(4) . .
C5 N8 N5 102.8(4) . .
N10 N9 Co1 126.5(3) . .
N12 N9 Co1 121.7(3) . .
N12 N9 N10 111.4(4) . .
N11 N10 N9 107.7(4) . .
C11 N11 N10 105.1(4) . .
C11 N12 N9 103.4(4) . .
C9 N13 C8 116.1(7) . .
C15 N14 C14 116.8(8) . .
H1c C1 N1 110.0(3) . .
H1d C1 N1 110.0(3) . .
H1d C1 H1c 108.4 . .
C2 C1 N1 108.3(5) . .
C2 C1 H1c 110.0(3) . .
C2 C1 H1d 110.0(3) . .
C1 C2 N2 106.7(4) . .
H2c C2 N2 110.4(3) . .
H2c C2 C1 110.4(4) . .
H2d C2 N2 110.4(3) . .
H2d C2 C1 110.4(3) . .
H2d C2 H2c 108.6 . .
H3c C3 N3 110.0(3) . .
H3d C3 N3 110.0(3) . .
H3d C3 H3c 108.4 . .
C4 C3 N3 108.6(5) . .
C4 C3 H3c 110.0(3) . .
C4 C3 H3d 110.0(4) . .
C3 C4 N4 108.0(5) . .
H4c C4 N4 110.1(3) . .
H4c C4 C3 110.1(3) . .
H4d C4 N4 110.1(3) . .
H4d C4 C3 110.1(4) . .
H4d C4 H4c 108.4 . .
N8 C5 N7 112.3(5) . .
C6 C5 N7 124.5(5) . .
C6 C5 N8 123.2(5) . .
C7 C6 C5 122.3(6) . .
C10 C6 C5 119.7(6) . .
C10 C6 C7 118.0(6) . .
H7 C7 C6 120.3(4) . .
C8 C7 C6 119.4(8) . .
C8 C7 H7 120.3(5) . .
C7 C8 N13 124.4(8) . .
H8 C8 N13 117.8(4) . .
H8 C8 C7 117.8(5) . .
H9 C9 N13 118.2(5) . .
C10 C9 N13 123.6(9) . .
C10 C9 H9 118.2(6) . .
C9 C10 C6 118.4(8) . .
H10 C10 C6 120.8(4) . .
H10 C10 C9 120.8(6) . .
N12 C11 N11 112.4(5) . .
C12 C11 N11 124.9(5) . .
C12 C11 N12 122.7(6) . .
C13 C12 C11 120.8(7) . .
C16 C12 C11 120.1(6) . .
C16 C12 C13 119.1(6) . .
H13 C13 C12 121.2(5) . .
C14 C13 C12 117.5(9) . .
C14 C13 H13 121.2(7) . .
C13 C14 N14 123.9(9) . .
H14 C14 N14 118.0(5) . .
H14 C14 C13 118.0(7) . .
H15 C15 N14 117.6(6) . .
C16 C15 N14 124.9(10) . .
C16 C15 H15 117.6(7) . .
C15 C16 C12 117.7(9) . .
H16 C16 C12 121.2(4) . .
H16 C16 C15 121.2(7) . .
O222 Cl1 O111 111.3(10) . .
O333 Cl1 O111 106.8(5) . .
O333 Cl1 O222 110.2(9) . .
O444 Cl1 O111 118.7(7) . .
O444 Cl1 O222 99.3(9) . .
O444 Cl1 O333 110.3(5) . .
H10b O101 H10a 109.5 . .

_database_code_depnum_ccdc_archive 'CCDC 933047'
#######################################################################
#
#                 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_6
_audit_creation_date             2014-04-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_chemical_formula_moiety         '3(C18 H24 Br2 Co N12), 2(Cl O4), Cl O3'
_chemical_formula_sum            'C54 H72 Br6 Cl3 Co3 N36 O11'
_chemical_formula_weight         2164.02
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Co 0.35655 0.96576 12.28410 7.34090 4.00340 2.34880 4.27910 0.27840 13.53590
71.16920 1.01180005074
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      trigonal
_space_group_IT_number           165
_space_group_name_H-M_alt        'P -3 c 1'
_space_group_name_Hall           '-P 3 2"c'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -y,x-y,z
3 -x+y,-x,z
4 x-y,-y,-z+1/2
5 -x,-x+y,-z+1/2
6 y,x,-z+1/2
7 -x,-y,-z
8 y,-x+y,-z
9 x-y,x,-z
10 -x+y,y,z-1/2
11 x,x-y,z-1/2
12 -y,-x,z-1/2

_symmetry_Int_Tables_number      165
_cell_length_a                   12.545(3)
_cell_length_b                   12.545(3)
_cell_length_c                   32.893(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4483(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_exptl_absorpt_coefficient_mu    3.381
_exptl_crystal_density_diffrn    1.6030
_exptl_crystal_F_000             2156.4258
_diffrn_reflns_av_R_equivalents  0.1818
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            33225
_diffrn_reflns_theta_full        29.8114
_diffrn_reflns_theta_max         29.81
_diffrn_reflns_theta_min         1.87
_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.365
_exptl_absorpt_correction_T_max  0.509
_diffrn_measured_fraction_theta_full 0.9834
_diffrn_measured_fraction_theta_max 0.9834
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              0
_reflns_limit_k_max              6
_reflns_limit_k_min              0
_reflns_limit_l_max              31
_reflns_limit_l_min              -32
_reflns_number_gt                4083
_reflns_number_total             4083
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
'L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation (2013)'
_computing_structure_solution    
'L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation (2013)'
_refine_diff_density_max         1.5757
_refine_diff_density_min         -0.6575
_refine_diff_density_rms         0.1400
_refine_ls_d_res_high            1.0002
_refine_ls_d_res_low             10.8641
_refine_ls_goodness_of_fit_ref   1.0840
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    17
_refine_ls_number_parameters     171
_refine_ls_number_reflns         1002
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0741
_refine_ls_restrained_S_all      1.0840
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1959P)²+5.2213P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2283
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C1(H1e,H1f), N1(H1c,H1d)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C5(H5), C6(H6), C9(H9)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
_atom_site_refinement_flags_adp
O3 O -0.0441(19) 0.000000 0.250000 0.130(12) Uiso 1.000000 S T
Co1 Co 0.3691(2) 0.000000 0.250000 0.0381(11) Uani 1.000000 S T
Cl2 Cl 0.000000 0.000000 0.250000 0.0094(19) Uani 1.000020 S T
Br1 Br 0.5893(4) -0.1510(3) -0.02039(8) 0.188(2) Uani 1.000000 . .
N2 N 0.2369(15) -0.0504(14) 0.2104(5) 0.049(4) Uani 1.000000 . .
N1 N 0.4423(9) 0.1568(9) 0.2217(3) 0.044(3) Uani 1.000000 . .
N4 N 0.4463(10) -0.0604(10) 0.2134(4) 0.046(3) Uani 1.000000 . .
N6 N 0.5294(11) -0.1615(11) 0.1905(4) 0.058(4) Uani 1.000000 . .
N5 N 0.4880(12) -0.1346(11) 0.2245(4) 0.056(3) Uani 1.000000 . .
C4 C 0.5418(13) -0.1064(13) 0.1172(5) 0.051(4) Uani 1.000000 . .
C3 C 0.5141(13) -0.0989(12) 0.1610(4) 0.045(4) Uani 1.000000 . .
C8 C 0.5736(19) -0.0279(17) 0.0494(6) 0.086(6) Uani 1.000000 . .
H8 H 0.5864(19) 0.0340(17) 0.0312(6) 0.104(7) Uiso 1.000000 R .
C2 C 0.2671(14) 0.0470(13) 0.1791(4) 0.053(4) Uani 1.000000 . .
H2a H 0.3092(14) 0.0355(13) 0.1562(4) 0.064(5) Uiso 1.000000 R .
H2b H 0.1925(14) 0.0433(13) 0.1692(4) 0.064(5) Uiso 1.000000 R .
N3 N 0.4629(10) -0.0337(10) 0.1743(4) 0.044(3) Uani 1.000000 . .
C1 C 0.3487(13) 0.1688(13) 0.1991(5) 0.055(4) Uani 1.000000 . .
H1e H 0.3011(13) 0.1895(13) 0.2174(5) 0.066(5) Uiso 1.000000 R .
H1f H 0.3871(13) 0.2332(13) 0.1788(5) 0.066(5) Uiso 1.000000 R .
C5 C 0.544(2) -0.2078(18) 0.1026(5) 0.092(6) Uani 1.000000 . .
H5 H 0.532(2) -0.2706(18) 0.1205(5) 0.110(7) Uiso 1.000000 R .
C7 C 0.573(2) -0.130(2) 0.0363(6) 0.107(8) Uani 1.000000 . .
C6 C 0.564(2) -0.218(2) 0.0636(7) 0.117(8) Uani 1.000000 . .
H6 H 0.572(2) -0.284(2) 0.0546(7) 0.141(10) Uiso 1.000000 R .
C9 C 0.5554(16) -0.0163(14) 0.0902(5) 0.065(5) Uani 1.000000 . .
H9 H 0.5522(16) 0.0521(14) 0.0995(5) 0.078(6) Uiso 1.000000 R .
Cl1 Cl 0.666667 0.333333 0.1323(2) 0.0540(19) Uani 1.000000 S T
O2 O 0.666667 0.333333 0.1758(6) 0.073(5) Uiso 1.000000 S T
O1 O 0.7092(11) 0.4554(11) 0.1184(3) 0.087(4) Uiso 1.000000 . .
H1a H 0.189(10) -0.063(11) 0.219(4) 0.00(4) Uiso 1.000000 . .
H1b H 0.232(15) -0.124(17) 0.194(5) 0.11(6) Uiso 1.000000 . .
H1c H 0.4785(9) 0.2185(9) 0.2398(3) 0.053(4) Uiso 1.000000 R .
H1d H 0.5005(9) 0.1623(9) 0.2045(3) 0.053(4) Uiso 1.000000 R .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O3 O3 0.96(4) 3
O3 O3 0.96(4) 2
O3 Cl2 0.55(2) 2
Co1 N2 1.949(15) .
Co1 N2 1.949(15) 4
Co1 N1 1.942(10) 4
Co1 N1 1.942(10) .
Co1 N4 1.921(12) .
Co1 N4 1.921(12) 4
Br1 C7 1.910(19) .
N2 C2 1.495(19) .
N1 C1 1.459(18) .
N4 N5 1.327(15) .
N4 N3 1.320(14) .
N6 N5 1.344(15) .
N6 C3 1.324(17) .
C4 C3 1.495(19) .
C4 C5 1.37(2) .
C4 C9 1.38(2) .
C3 N3 1.342(16) .
C8 C7 1.35(2) .
C8 C9 1.38(2) .
C2 C1 1.501(19) .
C5 C6 1.33(2) .
C7 C6 1.38(3) .
Cl1 O2 1.430(19) .
Cl1 O1 1.421(12) 3_665
Cl1 O1 1.421(12) .
Cl1 O1 1.421(12) 2_655

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
Cl2 O3 O3 30.0 2 3
N2 Co1 N2 92.9(10) 4 .
N1 Co1 N2 84.4(6) 4 4
N1 Co1 N2 92.9(6) 4 .
N1 Co1 N2 92.9(6) . 4
N1 Co1 N2 84.4(6) . .
N1 Co1 N1 176.1(7) 4 .
N4 Co1 N2 88.2(6) 4 4
N4 Co1 N2 175.7(6) 4 .
N4 Co1 N2 88.2(6) . .
N4 Co1 N2 175.7(6) . 4
N4 Co1 N1 91.3(5) 4 4
N4 Co1 N1 91.4(5) 4 .
N4 Co1 N1 91.3(5) . .
N4 Co1 N1 91.4(5) . 4
N4 Co1 N4 91.0(7) 4 .
O3 Cl2 O3 120.0 2 .
O3 Cl2 O3 120.0 2 3
O3 Cl2 O3 120.0 . 3
C2 N2 Co1 111.6(10) . .
C1 N1 Co1 110.6(8) . .
N5 N4 Co1 124.0(10) . .
N3 N4 Co1 123.8(9) . .
N3 N4 N5 112.2(11) . .
C3 N6 N5 105.8(11) . .
N6 N5 N4 106.6(11) . .
C5 C4 C3 120.5(14) . .
C9 C4 C3 120.4(14) . .
C9 C4 C5 118.9(15) . .
C4 C3 N6 124.3(14) . .
N3 C3 N6 112.2(12) . .
N3 C3 C4 123.4(13) . .
C9 C8 C7 119.2(17) . .
C1 C2 N2 107.1(12) . .
C3 N3 N4 103.1(11) . .
C2 C1 N1 107.1(11) . .
C6 C5 C4 121.1(17) . .
C8 C7 Br1 119.5(17) . .
C6 C7 Br1 119.9(16) . .
C6 C7 C8 120.7(18) . .
C7 C6 C5 119.9(18) . .
C8 C9 C4 119.9(15) . .
O1 Cl1 O2 108.7(5) 3_665 .
O1 Cl1 O2 108.7(5) . .
O1 Cl1 O2 108.7(5) 2_655 .
O1 Cl1 O1 110.2(5) 3_665 .
O1 Cl1 O1 110.2(5) 3_665 2_655
O1 Cl1 O1 110.2(5) . 2_655

_database_code_depnum_ccdc_archive 'CCDC 935043'
