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

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

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H34 Co N4 O4'
_chemical_formula_weight         693.64

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 2/c '

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

_cell_length_a                   23.6808(19)
_cell_length_b                   13.9240(12)
_cell_length_c                   10.9090(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.6020(10)
_cell_angle_gamma                90.00
_cell_volume                     3595.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1968
_cell_measurement_theta_min      3.86
_cell_measurement_theta_max      23.62

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1444
_exptl_absorpt_coefficient_mu    0.523
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.878
_exptl_absorpt_correction_T_max  0.9201
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine--focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10848
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_sigmaI/netI    0.0539
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         27.54
_reflns_number_total             4091
_reflns_number_gt                2811
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1998)'
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL  (Bruker, 1999)'
_computing_publication_material  SHELXTL

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0482P)²+0.7890P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4091
_refine_ls_number_parameters     224
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1117
_refine_ls_wR_factor_gt          0.0980
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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 0.5000 0.47807(3) 0.7500 0.03643(15) Uani 1 2 d S . .
O1 O 0.57320(8) 0.62468(15) 0.8201(2) 0.0803(6) Uani 1 1 d . . .
O2 O 0.56210(7) 0.52973(12) 0.65886(17) 0.0567(5) Uani 1 1 d . . .
N1 N 0.46219(7) 0.37645(12) 0.64181(17) 0.0393(4) Uani 1 1 d . . .
N2 N 0.45893(8) 0.25338(12) 0.51263(16) 0.0408(4) Uani 1 1 d . . .
C1 C 0.63876(9) 0.63750(18) 0.6595(2) 0.0489(6) Uani 1 1 d . . .
C2 C 0.65802(10) 0.59885(18) 0.5517(3) 0.0541(7) Uani 1 1 d . . .
H2 H 0.6415 0.5433 0.5198 0.065 Uiso 1 1 calc R . .
C3 C 0.70186(10) 0.64222(18) 0.4908(2) 0.0551(7) Uani 1 1 d . . .
H3 H 0.7145 0.6146 0.4189 0.066 Uiso 1 1 calc R . .
C4 C 0.72746(9) 0.72581(18) 0.5342(2) 0.0473(6) Uani 1 1 d . . .
C5 C 0.70781(11) 0.7623(2) 0.6439(3) 0.0659(8) Uani 1 1 d . . .
H5 H 0.7243 0.8175 0.6766 0.079 Uiso 1 1 calc R . .
C6 C 0.66444(11) 0.7186(2) 0.7055(3) 0.0634(7) Uani 1 1 d . . .
H6 H 0.6526 0.7446 0.7790 0.076 Uiso 1 1 calc R . .
C7 C 0.58810(10) 0.59519(19) 0.7203(3) 0.0542(7) Uani 1 1 d . . .
C8 C 0.48228(9) 0.33907(15) 0.5416(2) 0.0389(5) Uani 1 1 d . . .
H8 H 0.5097 0.3686 0.4953 0.047 Uiso 1 1 calc R . .
C9 C 0.42308(9) 0.30926(15) 0.6832(2) 0.0380(5) Uani 1 1 d . . .
C10 C 0.38970(9) 0.30971(17) 0.7866(2) 0.0469(6) Uani 1 1 d . . .
H10 H 0.3910 0.3613 0.8407 0.056 Uiso 1 1 calc R . .
C11 C 0.35475(10) 0.23230(19) 0.8073(2) 0.0542(6) Uani 1 1 d . . .
C12 C 0.35275(10) 0.15424(18) 0.7252(3) 0.0543(7) Uani 1 1 d . . .
C13 C 0.31983(14) 0.2321(3) 0.9209(3) 0.0902(11) Uani 1 1 d . . .
H13A H 0.3262 0.2906 0.9656 0.135 Uiso 1 1 calc R . .
H13B H 0.3305 0.1783 0.9716 0.135 Uiso 1 1 calc R . .
H13C H 0.2805 0.2271 0.8977 0.135 Uiso 1 1 calc R . .
C14 C 0.31483(13) 0.0681(2) 0.7481(3) 0.0829(10) Uani 1 1 d . . .
H14A H 0.3190 0.0220 0.6835 0.124 Uiso 1 1 calc R . .
H14B H 0.2762 0.0888 0.7499 0.124 Uiso 1 1 calc R . .
H14C H 0.3254 0.0392 0.8253 0.124 Uiso 1 1 calc R . .
C15 C 0.38553(10) 0.15403(17) 0.6228(2) 0.0499(6) Uani 1 1 d . . .
H15 H 0.3841 0.1028 0.5682 0.060 Uiso 1 1 calc R . .
C16 C 0.42085(9) 0.23241(15) 0.6029(2) 0.0402(5) Uani 1 1 d . . .
C17 C 0.47487(11) 0.19228(16) 0.4105(2) 0.0518(6) Uani 1 1 d . . .
H17A H 0.5073 0.2197 0.3710 0.062 Uiso 1 1 calc R . .
H17B H 0.4439 0.1892 0.3504 0.062 Uiso 1 1 calc R . .
C18 C 0.48903(10) 0.09236(16) 0.4552(2) 0.0445(6) Uani 1 1 d . . .
C19 C 0.52360(11) 0.07818(17) 0.5582(2) 0.0526(6) Uani 1 1 d . . .
H19 H 0.5397 0.1309 0.5982 0.063 Uiso 1 1 calc R . .
C20 C 0.53439(11) -0.01299(17) 0.6021(2) 0.0524(6) Uani 1 1 d . . .
H20 H 0.5578 -0.0211 0.6712 0.063 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O2 1.9365(15) . ?
Co1 O2 1.9365(15) 2_656 ?
Co1 N1 2.0341(18) . ?
Co1 N1 2.0341(18) 2_656 ?
O1 C7 1.225(3) . ?
O2 C7 1.279(3) . ?
N1 C8 1.312(3) . ?
N1 C9 1.400(3) . ?
N2 C8 1.349(3) . ?
N2 C16 1.385(3) . ?
N2 C17 1.460(3) . ?
C1 C6 1.371(3) . ?
C1 C2 1.382(3) . ?
C1 C7 1.507(3) . ?
C2 C3 1.387(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.389(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(4) . ?
C4 C4 1.482(4) 7_666 ?
C5 C6 1.384(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 H8 0.9300 . ?
C9 C16 1.383(3) . ?
C9 C10 1.395(3) . ?
C10 C11 1.381(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.408(4) . ?
C11 C13 1.509(3) . ?
C12 C15 1.378(3) . ?
C12 C14 1.523(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.396(3) . ?
C15 H15 0.9300 . ?
C17 C18 1.509(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C20 1.378(3) 5_656 ?
C18 C19 1.386(3) . ?
C19 C20 1.378(3) . ?
C19 H19 0.9300 . ?
C20 C18 1.378(3) 5_656 ?
C20 H20 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Co1 O2 136.39(11) . 2_656 ?
O2 Co1 N1 106.78(8) . . ?
O2 Co1 N1 103.18(7) 2_656 . ?
O2 Co1 N1 103.18(7) . 2_656 ?
O2 Co1 N1 106.78(8) 2_656 2_656 ?
N1 Co1 N1 91.85(10) . 2_656 ?
C7 O2 Co1 110.92(16) . . ?
C8 N1 C9 105.21(18) . . ?
C8 N1 Co1 126.54(15) . . ?
C9 N1 Co1 124.19(15) . . ?
C8 N2 C16 106.92(18) . . ?
C8 N2 C17 125.52(19) . . ?
C16 N2 C17 127.40(19) . . ?
C6 C1 C2 118.6(2) . . ?
C6 C1 C7 120.8(2) . . ?
C2 C1 C7 120.5(2) . . ?
C1 C2 C3 120.5(2) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C4 121.8(2) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C3 C4 C5 116.4(2) . . ?
C3 C4 C4 121.5(3) . 7_666 ?
C5 C4 C4 122.0(3) . 7_666 ?
C6 C5 C4 121.9(3) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C1 C6 C5 120.8(3) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
O1 C7 O2 123.9(2) . . ?
O1 C7 C1 120.8(3) . . ?
O2 C7 C1 115.2(2) . . ?
N1 C8 N2 112.95(19) . . ?
N1 C8 H8 123.5 . . ?
N2 C8 H8 123.5 . . ?
C16 C9 C10 120.2(2) . . ?
C16 C9 N1 109.04(19) . . ?
C10 C9 N1 130.7(2) . . ?
C11 C10 C9 119.0(2) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C10 C11 C12 120.5(2) . . ?
C10 C11 C13 118.7(3) . . ?
C12 C11 C13 120.7(2) . . ?
C15 C12 C11 120.5(2) . . ?
C15 C12 C14 118.6(3) . . ?
C11 C12 C14 120.9(3) . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 C16 118.6(2) . . ?
C12 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C9 C16 N2 105.87(18) . . ?
C9 C16 C15 121.2(2) . . ?
N2 C16 C15 132.9(2) . . ?
N2 C17 C18 110.53(19) . . ?
N2 C17 H17A 109.5 . . ?
C18 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
C20 C18 C19 118.3(2) 5_656 . ?
C20 C18 C17 120.7(2) 5_656 . ?
C19 C18 C17 120.9(2) . . ?
C20 C19 C18 120.8(2) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C18 120.9(2) . 5_656 ?
C19 C20 H20 119.6 . . ?
C18 C20 H20 119.6 5_656 . ?

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
O2 Co1 O2 C7 48.02(15) 2_656 . . . ?
N1 Co1 O2 C7 179.46(15) . . . . ?
N1 Co1 O2 C7 -84.49(17) 2_656 . . . ?
O2 Co1 N1 C8 12.6(2) . . . . ?
O2 Co1 N1 C8 160.54(18) 2_656 . . . ?
N1 Co1 N1 C8 -91.74(18) 2_656 . . . ?
O2 Co1 N1 C9 166.55(15) . . . . ?
O2 Co1 N1 C9 -45.53(17) 2_656 . . . ?
N1 Co1 N1 C9 62.19(15) 2_656 . . . ?
C6 C1 C2 C3 -0.9(4) . . . . ?
C7 C1 C2 C3 175.0(2) . . . . ?
C1 C2 C3 C4 -0.7(4) . . . . ?
C2 C3 C4 C5 1.7(4) . . . . ?
C2 C3 C4 C4 -177.2(3) . . . 7_666 ?
C3 C4 C5 C6 -1.0(4) . . . . ?
C4 C4 C5 C6 177.9(3) 7_666 . . . ?
C2 C1 C6 C5 1.6(4) . . . . ?
C7 C1 C6 C5 -174.3(2) . . . . ?
C4 C5 C6 C1 -0.6(4) . . . . ?
Co1 O2 C7 O1 -4.1(3) . . . . ?
Co1 O2 C7 C1 177.64(15) . . . . ?
C6 C1 C7 O1 -9.4(4) . . . . ?
C2 C1 C7 O1 174.8(2) . . . . ?
C6 C1 C7 O2 168.9(2) . . . . ?
C2 C1 C7 O2 -6.9(3) . . . . ?
C9 N1 C8 N2 1.0(2) . . . . ?
Co1 N1 C8 N2 158.82(14) . . . . ?
C16 N2 C8 N1 -0.9(2) . . . . ?
C17 N2 C8 N1 -176.5(2) . . . . ?
C8 N1 C9 C16 -0.6(2) . . . . ?
Co1 N1 C9 C16 -159.16(14) . . . . ?
C8 N1 C9 C10 178.6(2) . . . . ?
Co1 N1 C9 C10 20.1(3) . . . . ?
C16 C9 C10 C11 0.2(3) . . . . ?
N1 C9 C10 C11 -178.9(2) . . . . ?
C9 C10 C11 C12 -0.1(4) . . . . ?
C9 C10 C11 C13 178.5(2) . . . . ?
C10 C11 C12 C15 -0.2(4) . . . . ?
C13 C11 C12 C15 -178.8(3) . . . . ?
C10 C11 C12 C14 179.3(2) . . . . ?
C13 C11 C12 C14 0.7(4) . . . . ?
C11 C12 C15 C16 0.4(4) . . . . ?
C14 C12 C15 C16 -179.1(2) . . . . ?
C10 C9 C16 N2 -179.2(2) . . . . ?
N1 C9 C16 N2 0.1(2) . . . . ?
C10 C9 C16 C15 0.0(3) . . . . ?
N1 C9 C16 C15 179.31(19) . . . . ?
C8 N2 C16 C9 0.5(2) . . . . ?
C17 N2 C16 C9 175.9(2) . . . . ?
C8 N2 C16 C15 -178.6(2) . . . . ?
C17 N2 C16 C15 -3.2(4) . . . . ?
C12 C15 C16 C9 -0.3(3) . . . . ?
C12 C15 C16 N2 178.7(2) . . . . ?
C8 N2 C17 C18 126.2(2) . . . . ?
C16 N2 C17 C18 -48.4(3) . . . . ?
N2 C17 C18 C20 130.7(2) . . . 5_656 ?
N2 C17 C18 C19 -46.1(3) . . . . ?
C20 C18 C19 C20 0.1(4) 5_656 . . . ?
C17 C18 C19 C20 177.0(2) . . . . ?
C18 C19 C20 C18 -0.1(4) . . . 5_656 ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.048
_database_code_depnum_ccdc_archive 'CCDC 1013903'
#######################################################################
#
#                 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_x

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H32 Co N5 O7.50'
_chemical_formula_weight         689.58

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 2/c '

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

_cell_length_a                   19.054(3)
_cell_length_b                   16.004(2)
_cell_length_c                   21.248(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.471(2)
_cell_angle_gamma                90.00
_cell_volume                     6371.4(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3018
_cell_measurement_theta_min      3.36
_cell_measurement_theta_max      21.38

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2864
_exptl_absorpt_coefficient_mu    0.598
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8568
_exptl_absorpt_correction_T_max  0.9138
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine--focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19225
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_sigmaI/netI    0.0929
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         27.55
_reflns_number_total             7294
_reflns_number_gt                3798
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1998)'
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL  (Bruker, 1999)'
_computing_publication_material  SHELXTL

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0834P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7294
_refine_ls_number_parameters     455
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.1196
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1656
_refine_ls_wR_factor_gt          0.1380
_refine_ls_goodness_of_fit_ref   0.906
_refine_ls_restrained_S_all      0.906
_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 0.68294(3) 0.83570(3) 0.55356(2) 0.04087(17) Uani 1 1 d . . .
O1 O 0.7784(3) 0.9045(3) 0.7469(2) 0.1300(17) Uani 1 1 d . . .
O2 O 0.8058(4) 0.8348(3) 0.8307(2) 0.165(2) Uani 1 1 d . . .
O3 O 0.87677(17) 0.8970(2) 0.65405(15) 0.0832(10) Uani 1 1 d . A .
O4 O 0.76593(19) 0.8874(2) 0.6036(2) 0.1192(16) Uani 1 1 d . A .
O5 O 0.8455(4) 0.6539(5) 0.5405(4) 0.0529(18) Uani 0.50 1 d PDU . 1
O6 O 0.7822(3) 0.7674(3) 0.5349(2) 0.0547(13) Uani 0.50 1 d PDU A 1
O5B O 0.8080(4) 0.6233(6) 0.5394(4) 0.077(2) Uani 0.50 1 d PDU . 2
O6B O 0.8691(4) 0.7402(5) 0.5497(3) 0.096(2) Uani 0.50 1 d PDU B 2
N1 N 0.65502(15) 0.73002(16) 0.59532(12) 0.0394(7) Uani 1 1 d . A .
N2 N 0.64251(16) 0.59480(17) 0.61179(13) 0.0458(7) Uani 1 1 d . A .
N3 N 0.60145(15) 0.91038(16) 0.57131(12) 0.0374(6) Uani 1 1 d . A .
N4 N 0.53880(16) 1.01999(16) 0.59350(12) 0.0385(7) Uani 1 1 d . A .
N5 N 0.7977(3) 0.8412(3) 0.7735(2) 0.0889(14) Uani 1 1 d . . .
C1 C 0.65739(18) 0.6548(2) 0.57199(16) 0.0417(8) Uani 1 1 d . . .
H1 H 0.6683 0.6438 0.5319 0.050 Uiso 1 1 calc R A .
C2 C 0.63597(18) 0.7190(2) 0.65471(15) 0.0394(8) Uani 1 1 d . . .
C3 C 0.6264(2) 0.7777(2) 0.70094(16) 0.0479(9) Uani 1 1 d . A .
H3 H 0.6315 0.8345 0.6935 0.058 Uiso 1 1 calc R . .
C5 C 0.6007(2) 0.6638(3) 0.76837(19) 0.0661(12) Uani 1 1 d . A .
C6 C 0.6106(2) 0.6056(2) 0.72257(18) 0.0592(11) Uani 1 1 d . . .
H6 H 0.6054 0.5488 0.7296 0.071 Uiso 1 1 calc R A .
C7 C 0.62824(19) 0.6343(2) 0.66605(16) 0.0451(9) Uani 1 1 d . A .
C8 C 0.5990(3) 0.8135(3) 0.8085(2) 0.0887(16) Uani 1 1 d . A .
H8A H 0.6077 0.8687 0.7940 0.133 Uiso 1 1 calc R . .
H8B H 0.6319 0.8018 0.8473 0.133 Uiso 1 1 calc R . .
H8C H 0.5510 0.8101 0.8163 0.133 Uiso 1 1 calc R . .
C9 C 0.5794(3) 0.6341(3) 0.8309(2) 0.1015(19) Uani 1 1 d . . .
H9A H 0.6155 0.6503 0.8664 0.152 Uiso 1 1 calc R A .
H9B H 0.5747 0.5744 0.8301 0.152 Uiso 1 1 calc R . .
H9C H 0.5347 0.6590 0.8352 0.152 Uiso 1 1 calc R . .
C10 C 0.6305(2) 0.5063(2) 0.5938(2) 0.0619(11) Uani 1 1 d . . .
H10A H 0.6262 0.4735 0.6313 0.074 Uiso 1 1 calc R A .
H10B H 0.6706 0.4851 0.5763 0.074 Uiso 1 1 calc R . .
C11 C 0.5636(2) 0.4992(2) 0.54506(17) 0.0495(9) Uani 1 1 d . . .
C12 C 0.5649(2) 0.5098(3) 0.48088(19) 0.0609(11) Uani 1 1 d . . .
H12 H 0.6083 0.5162 0.4673 0.073 Uiso 1 1 calc R A .
C13 C 0.5022(2) 0.5110(2) 0.43665(18) 0.0609(11) Uani 1 1 d . . .
H13 H 0.5040 0.5187 0.3936 0.073 Uiso 1 1 calc R . .
C14 C 0.60434(19) 0.9872(2) 0.59350(15) 0.0412(8) Uani 1 1 d . . .
H14 H 0.6467 1.0159 0.6077 0.049 Uiso 1 1 calc R A .
C15 C 0.52901(19) 0.8909(2) 0.55647(14) 0.0370(8) Uani 1 1 d . . .
C16 C 0.4939(2) 0.8191(2) 0.53105(16) 0.0455(9) Uani 1 1 d . A .
H16 H 0.5198 0.7729 0.5218 0.055 Uiso 1 1 calc R . .
C17 C 0.4208(2) 0.8171(2) 0.51970(17) 0.0536(10) Uani 1 1 d . . .
C18 C 0.3809(2) 0.8873(3) 0.53329(17) 0.0535(10) Uani 1 1 d . A .
C19 C 0.4152(2) 0.9583(2) 0.55886(15) 0.0473(9) Uani 1 1 d . . .
H19 H 0.3895 1.0045 0.5685 0.057 Uiso 1 1 calc R A .
C20 C 0.48950(18) 0.9597(2) 0.56997(14) 0.0374(8) Uani 1 1 d . A .
C21 C 0.3832(3) 0.7383(3) 0.4917(2) 0.0791(14) Uani 1 1 d . A .
H21A H 0.3555 0.7504 0.4503 0.119 Uiso 1 1 calc R . .
H21B H 0.3524 0.7183 0.5195 0.119 Uiso 1 1 calc R . .
H21C H 0.4181 0.6963 0.4876 0.119 Uiso 1 1 calc R . .
C22 C 0.3002(2) 0.8855(4) 0.5210(2) 0.0888(15) Uani 1 1 d . . .
H22A H 0.2842 0.8438 0.5477 0.133 Uiso 1 1 calc R A .
H22B H 0.2828 0.8723 0.4769 0.133 Uiso 1 1 calc R . .
H22C H 0.2825 0.9392 0.5307 0.133 Uiso 1 1 calc R . .
C23 C 0.5247(2) 1.1023(2) 0.61931(15) 0.0455(9) Uani 1 1 d . . .
H23A H 0.4833 1.1267 0.5923 0.055 Uiso 1 1 calc R A .
H23B H 0.5651 1.1386 0.6177 0.055 Uiso 1 1 calc R . .
C24 C 0.51183(18) 1.0989(2) 0.68686(14) 0.0370(8) Uani 1 1 d . A .
C25 C 0.5061(2) 1.0251(2) 0.71888(14) 0.0428(9) Uani 1 1 d . . .
H25 H 0.5105 0.9745 0.6984 0.051 Uiso 1 1 calc R A .
C26 C 0.6091(2) 0.7504(3) 0.75775(17) 0.0585(11) Uani 1 1 d . . .
C27 C 0.5056(2) 1.1731(2) 0.71923(15) 0.0421(9) Uani 1 1 d . . .
H27 H 0.5092 1.2237 0.6986 0.050 Uiso 1 1 calc R A .
C28 C 0.81489(18) 0.7750(2) 0.67179(16) 0.0456(9) Uani 1 1 d . A .
C29 C 0.8205(2) 0.7010(3) 0.63902(15) 0.0487(9) Uani 1 1 d D . .
C30 C 0.8183(2) 0.6244(3) 0.66904(18) 0.0582(11) Uani 1 1 d . . .
H30 H 0.8227 0.5756 0.6463 0.070 Uiso 1 1 calc R . .
C31 C 0.8098(2) 0.6192(3) 0.73184(17) 0.0580(11) Uani 1 1 d . . .
H31 H 0.8074 0.5675 0.7513 0.070 Uiso 1 1 calc R A .
C32 C 0.8049(2) 0.6910(3) 0.76489(18) 0.0598(11) Uani 1 1 d . . .
H32 H 0.7999 0.6888 0.8076 0.072 Uiso 1 1 calc R . .
C33 C 0.8075(2) 0.7670(2) 0.73509(16) 0.0505(9) Uani 1 1 d . . .
C34 C 0.8208(3) 0.8608(3) 0.6410(2) 0.0654(12) Uani 1 1 d . . .
C35 C 0.8176(6) 0.7122(6) 0.5667(3) 0.041(3) Uani 0.50 1 d PDU A 1
C35B C 0.8357(7) 0.6830(8) 0.5715(4) 0.062(4) Uani 0.50 1 d PDU B 2
O1W O 0.9711(5) 0.9038(5) 0.7772(4) 0.135(3) Uani 0.50 1 d P . .
H1A H 0.9310 0.8866 0.7619 0.202 Uiso 0.50 1 d PR . .
H1B H 0.9993 0.9082 0.7502 0.202 Uiso 1 2 d SR . .


_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 O4 1.924(3) . ?
Co1 O5 1.980(8) 7_666 ?
Co1 N1 2.025(3) . ?
Co1 N3 2.048(3) . ?
Co1 O5B 2.117(8) 7_666 ?
Co1 O6 2.281(5) . ?
O1 N5 1.185(5) . ?
O2 N5 1.201(5) . ?
O3 C34 1.201(5) . ?
O4 C34 1.268(5) . ?
O5 C35 1.253(10) . ?
O5 Co1 1.980(8) 7_666 ?
O6 C35 1.235(8) . ?
O5B C35B 1.235(13) . ?
O5B Co1 2.117(8) 7_666 ?
O6B C35B 1.252(13) . ?
N1 C1 1.306(4) . ?
N1 C2 1.387(4) . ?
N2 C1 1.343(4) . ?
N2 C7 1.385(4) . ?
N2 C10 1.473(4) . ?
N3 C14 1.314(4) . ?
N3 C15 1.394(4) . ?
N4 C14 1.355(4) . ?
N4 C20 1.376(4) . ?
N4 C23 1.471(4) . ?
N5 C33 1.472(5) . ?
C1 H1 0.9300 . ?
C2 C7 1.388(5) . ?
C2 C3 1.395(4) . ?
C3 C26 1.379(5) . ?
C3 H3 0.9300 . ?
C5 C6 1.385(6) . ?
C5 C26 1.418(6) . ?
C5 C9 1.533(5) . ?
C6 C7 1.384(5) . ?
C6 H6 0.9300 . ?
C8 C26 1.515(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.493(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.379(5) . ?
C11 C13 1.388(5) 5_666 ?
C12 C13 1.380(6) . ?
C12 H12 0.9300 . ?
C13 C11 1.388(5) 5_666 ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.388(5) . ?
C15 C20 1.392(4) . ?
C16 C17 1.371(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.415(6) . ?
C17 C21 1.518(5) . ?
C18 C19 1.373(5) . ?
C18 C22 1.511(6) . ?
C19 C20 1.392(5) . ?
C19 H19 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.501(4) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.378(4) . ?
C24 C27 1.388(4) . ?
C25 C25 1.384(6) 2_656 ?
C25 H25 0.9300 . ?
C27 C27 1.363(6) 2_656 ?
C27 H27 0.9300 . ?
C28 C33 1.384(5) . ?
C28 C29 1.388(5) . ?
C28 C34 1.533(5) . ?
C29 C30 1.386(5) . ?
C29 C35B 1.541(8) . ?
C29 C35 1.538(7) . ?
C30 C31 1.376(5) . ?
C30 H30 0.9300 . ?
C31 C32 1.358(5) . ?
C31 H31 0.9300 . ?
C32 C33 1.376(5) . ?
C32 H32 0.9300 . ?
O1W O1W 1.736(17) 2_756 ?
O1W H1A 0.8231 . ?
O1W H1B 0.8565 . ?

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
O4 Co1 O5 124.6(3) . 7_666 ?
O4 Co1 N1 111.82(12) . . ?
O5 Co1 N1 117.8(2) 7_666 . ?
O4 Co1 N3 102.83(16) . . ?
O5 Co1 N3 93.4(2) 7_666 . ?
N1 Co1 N3 97.95(11) . . ?
O4 Co1 O5B 100.6(3) . 7_666 ?
O5 Co1 O5B 24.0(3) 7_666 7_666 ?
N1 Co1 O5B 137.7(3) . 7_666 ?
N3 Co1 O5B 100.6(2) . 7_666 ?
O4 Co1 O6 71.2(2) . . ?
O5 Co1 O6 87.0(2) 7_666 . ?
N1 Co1 O6 88.19(15) . . ?
N3 Co1 O6 172.78(16) . . ?
O5B Co1 O6 77.0(2) 7_666 . ?
C34 O4 Co1 134.8(3) . . ?
C35 O5 Co1 109.0(6) . 7_666 ?
C35 O6 Co1 129.4(5) . . ?
C35B O5B Co1 100.3(7) . 7_666 ?
C1 N1 C2 105.1(3) . . ?
C1 N1 Co1 125.0(2) . . ?
C2 N1 Co1 129.7(2) . . ?
C1 N2 C7 107.1(3) . . ?
C1 N2 C10 124.3(3) . . ?
C7 N2 C10 127.6(3) . . ?
C14 N3 C15 105.4(3) . . ?
C14 N3 Co1 128.9(2) . . ?
C15 N3 Co1 125.5(2) . . ?
C14 N4 C20 107.3(3) . . ?
C14 N4 C23 125.3(3) . . ?
C20 N4 C23 127.3(3) . . ?
O1 N5 O2 121.8(5) . . ?
O1 N5 C33 119.0(5) . . ?
O2 N5 C33 119.0(5) . . ?
N1 C1 N2 113.2(3) . . ?
N1 C1 H1 123.4 . . ?
N2 C1 H1 123.4 . . ?
N1 C2 C7 109.6(3) . . ?
N1 C2 C3 130.1(3) . . ?
C7 C2 C3 120.2(3) . . ?
C26 C3 C2 119.0(3) . . ?
C26 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C6 C5 C26 120.8(3) . . ?
C6 C5 C9 119.4(4) . . ?
C26 C5 C9 119.8(4) . . ?
C7 C6 C5 118.2(4) . . ?
C7 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
C6 C7 N2 133.4(3) . . ?
C6 C7 C2 121.7(3) . . ?
N2 C7 C2 105.0(3) . . ?
C26 C8 H8A 109.5 . . ?
C26 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C26 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 C11 109.0(3) . . ?
N2 C10 H10A 109.9 . . ?
C11 C10 H10A 109.9 . . ?
N2 C10 H10B 109.9 . . ?
C11 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
C12 C11 C13 118.1(4) . 5_666 ?
C12 C11 C10 120.7(4) . . ?
C13 C11 C10 121.0(4) 5_666 . ?
C13 C12 C11 120.4(4) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C11 121.5(4) . 5_666 ?
C12 C13 H13 119.3 . . ?
C11 C13 H13 119.3 5_666 . ?
N3 C14 N4 112.6(3) . . ?
N3 C14 H14 123.7 . . ?
N4 C14 H14 123.7 . . ?
C16 C15 N3 131.3(3) . . ?
C16 C15 C20 119.6(3) . . ?
N3 C15 C20 109.1(3) . . ?
C17 C16 C15 119.3(3) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 120.8(4) . . ?
C16 C17 C21 118.7(4) . . ?
C18 C17 C21 120.5(4) . . ?
C19 C18 C17 120.1(4) . . ?
C19 C18 C22 118.7(4) . . ?
C17 C18 C22 121.1(4) . . ?
C18 C19 C20 118.5(3) . . ?
C18 C19 H19 120.8 . . ?
C20 C19 H19 120.8 . . ?
N4 C20 C19 132.7(3) . . ?
N4 C20 C15 105.7(3) . . ?
C19 C20 C15 121.6(3) . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C22 H22A 109.5 . . ?
C18 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C18 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N4 C23 C24 113.4(3) . . ?
N4 C23 H23A 108.9 . . ?
C24 C23 H23A 108.9 . . ?
N4 C23 H23B 108.9 . . ?
C24 C23 H23B 108.9 . . ?
H23A C23 H23B 107.7 . . ?
C25 C24 C27 117.9(3) . . ?
C25 C24 C23 123.0(3) . . ?
C27 C24 C23 119.1(3) . . ?
C24 C25 C25 120.94(18) . 2_656 ?
C24 C25 H25 119.5 . . ?
C25 C25 H25 119.5 2_656 . ?
C3 C26 C5 120.1(3) . . ?
C3 C26 C8 119.5(4) . . ?
C5 C26 C8 120.4(4) . . ?
C27 C27 C24 121.19(18) 2_656 . ?
C27 C27 H27 119.4 2_656 . ?
C24 C27 H27 119.4 . . ?
C33 C28 C29 116.0(3) . . ?
C33 C28 C34 121.7(4) . . ?
C29 C28 C34 122.1(3) . . ?
C30 C29 C28 120.8(3) . . ?
C30 C29 C35B 106.8(5) . . ?
C28 C29 C35B 132.1(6) . . ?
C30 C29 C35 124.3(5) . . ?
C28 C29 C35 114.2(5) . . ?
C35B C29 C35 21.7(4) . . ?
C31 C30 C29 121.2(4) . . ?
C31 C30 H30 119.4 . . ?
C29 C30 H30 119.4 . . ?
C32 C31 C30 118.8(4) . . ?
C32 C31 H31 120.6 . . ?
C30 C31 H31 120.6 . . ?
C33 C32 C31 119.9(3) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
C32 C33 C28 123.2(3) . . ?
C32 C33 N5 116.1(4) . . ?
C28 C33 N5 120.6(4) . . ?
O3 C34 O4 125.4(4) . . ?
O3 C34 C28 117.8(4) . . ?
O4 C34 C28 116.9(4) . . ?
O6 C35 O5 121.5(7) . . ?
O6 C35 C29 123.2(7) . . ?
O5 C35 C29 114.6(7) . . ?
O5B C35B O6B 123.7(9) . . ?
O5B C35B C29 121.8(10) . . ?
O6B C35B C29 113.7(9) . . ?
O1W O1W H1A 113.1 2_756 . ?
O1W O1W H1B 4.7 2_756 . ?
H1A O1W H1B 114.4 . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.061
# SQUEEZE RESULTS (APPEND TO CIF, one water molecule)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.226 0.059 0.851 15 6 ' '
2 0.774 0.059 0.649 15 6 ' '
3 0.024 0.190 0.108 12 2 ' '
4 -0.024 0.190 0.392 12 2 ' '
5 0.476 0.309 0.892 12 2 ' '
6 0.524 0.309 0.608 12 2 ' '
7 0.274 0.440 0.149 15 6 ' '
8 0.726 0.440 0.351 15 6 ' '
9 0.274 0.559 0.649 15 6 ' '
10 0.726 0.559 0.851 15 6 ' '
11 0.476 0.690 0.392 12 2 ' '
12 0.524 0.690 0.108 12 2 ' '
13 0.024 0.809 0.608 12 2 ' '
14 -0.024 0.809 0.892 12 2 ' '
15 0.226 0.940 0.351 15 6 ' '
16 0.774 0.940 0.149 15 6 ' '
_platon_squeeze_details          ?
_database_code_depnum_ccdc_archive 'CCDC 1013904'
#######################################################################
#
#                 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_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H34 Co N4 O4'
_chemical_formula_weight         693.64

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           orthorhombic
_symmetry_space_group_name_H-M   'pbca '
_symmetry_space_group_name_Hall  '-P 2ac 2ab '

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'
'-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                   11.4409(12)
_cell_length_b                   24.696(3)
_cell_length_c                   25.285(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     7144.1(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2018
_cell_measurement_theta_min      4.21
_cell_measurement_theta_max      18.32

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2888
_exptl_absorpt_coefficient_mu    0.526
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8821
_exptl_absorpt_correction_T_max  0.9318
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine--focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            52018
_diffrn_reflns_av_R_equivalents  0.1422
_diffrn_reflns_av_sigmaI/netI    0.0900
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         25.02
_reflns_number_total             6304
_reflns_number_gt                3299
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1998)'
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL  (Bruker, 1999)'
_computing_publication_material  SHELXTL

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1545P)²+0.3452P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6304
_refine_ls_number_parameters     446
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1349
_refine_ls_R_factor_gt           0.0589
_refine_ls_wR_factor_ref         0.2342
_refine_ls_wR_factor_gt          0.1667
_refine_ls_goodness_of_fit_ref   0.883
_refine_ls_restrained_S_all      0.883
_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 0.37909(6) 0.54942(3) 0.60015(3) 0.0501(3) Uani 1 1 d . . .
O2 O 0.4921(3) 0.48944(15) 0.56806(16) 0.0656(10) Uani 1 1 d . . .
O1 O 0.3861(4) 0.46652(17) 0.63562(15) 0.0746(12) Uani 1 1 d . . .
N1 N 0.2664(4) 0.53647(16) 0.53725(15) 0.0495(10) Uani 1 1 d . . .
N2 N 0.1975(4) 0.49885(17) 0.46324(15) 0.0533(11) Uani 1 1 d . . .
N4 N -0.1289(4) 0.4372(2) 0.27973(16) 0.0618(13) Uani 1 1 d . . .
C37 C 0.8946(4) 0.1719(2) 0.60500(19) 0.0498(13) Uani 1 1 d . . .
C31 C 0.6618(5) 0.3079(2) 0.60398(19) 0.0499(13) Uani 1 1 d . . .
C40 C 0.9770(5) 0.1256(2) 0.60452(19) 0.0517(13) Uani 1 1 d . . .
C7 C 0.1227(4) 0.5412(2) 0.4752(2) 0.0506(13) Uani 1 1 d . . .
C28 C 0.5219(4) 0.4012(2) 0.60222(19) 0.0497(12) Uani 1 1 d . . .
C27 C 0.4617(5) 0.4554(2) 0.6020(2) 0.0537(13) Uani 1 1 d . . .
C39 C 0.7217(5) 0.2166(2) 0.63789(19) 0.0548(13) Uani 1 1 d . . .
H39 H 0.6570 0.2166 0.6601 0.066 Uiso 1 1 calc R . .
C38 C 0.7976(5) 0.1726(2) 0.63754(19) 0.0518(13) Uani 1 1 d . . .
H38 H 0.7827 0.1432 0.6595 0.062 Uiso 1 1 calc R . .
C34 C 0.7426(5) 0.26095(19) 0.60499(19) 0.0502(12) Uani 1 1 d . . .
C2 C 0.1673(5) 0.5651(2) 0.5208(2) 0.0533(13) Uani 1 1 d . . .
C32 C 0.6047(5) 0.3260(2) 0.6491(2) 0.0560(14) Uani 1 1 d . . .
H32 H 0.6138 0.3072 0.6806 0.067 Uiso 1 1 calc R . .
C29 C 0.5762(5) 0.3830(2) 0.55728(19) 0.0549(14) Uani 1 1 d . . .
H29 H 0.5671 0.4022 0.5259 0.066 Uiso 1 1 calc R . .
C26 C -0.1427(5) 0.3817(3) 0.28342(19) 0.0583(14) Uani 1 1 d . . .
C33 C 0.5343(5) 0.3716(2) 0.6478(2) 0.0578(14) Uani 1 1 d . . .
H33 H 0.4951 0.3823 0.6782 0.069 Uiso 1 1 calc R . .
C3 C 0.1164(5) 0.6115(2) 0.5415(2) 0.0660(16) Uani 1 1 d . . .
H3 H 0.1473 0.6281 0.5714 0.079 Uiso 1 1 calc R . .
C1 C 0.2802(4) 0.4985(2) 0.50155(18) 0.0497(12) Uani 1 1 d . . .
H1 H 0.3413 0.4737 0.5024 0.060 Uiso 1 1 calc R . .
C11 C 0.1657(5) 0.4864(2) 0.36753(19) 0.0540(14) Uani 1 1 d . . .
C18 C -0.2033(5) 0.4599(2) 0.3138(2) 0.0614(15) Uani 1 1 d . . .
H18 H -0.2088 0.4971 0.3189 0.074 Uiso 1 1 calc R . .
C36 C 0.9155(6) 0.2160(2) 0.5728(3) 0.0740(18) Uani 1 1 d . . .
H36 H 0.9804 0.2161 0.5507 0.089 Uiso 1 1 calc R . .
C35 C 0.8415(5) 0.2597(2) 0.5733(2) 0.0718(17) Uani 1 1 d . . .
H35 H 0.8581 0.2893 0.5518 0.086 Uiso 1 1 calc R . .
C19 C -0.2308(5) 0.3737(2) 0.32116(19) 0.0569(14) Uani 1 1 d . . .
C30 C 0.6435(5) 0.3373(2) 0.5578(2) 0.0598(15) Uani 1 1 d . . .
H30 H 0.6779 0.3256 0.5265 0.072 Uiso 1 1 calc R . .
C6 C 0.0225(5) 0.5611(3) 0.4506(2) 0.0691(17) Uani 1 1 d . . .
H6 H -0.0084 0.5440 0.4209 0.083 Uiso 1 1 calc R . .
C15 C 0.0561(4) 0.4875(2) 0.28582(18) 0.0553(14) Uani 1 1 d . . .
C16 C 0.0810(5) 0.4653(2) 0.3345(2) 0.0559(14) Uani 1 1 d . . .
H16 H 0.0394 0.4350 0.3455 0.067 Uiso 1 1 calc R . .
C14 C 0.1193(5) 0.5325(3) 0.2707(2) 0.0724(17) Uani 1 1 d . . .
H14 H 0.1045 0.5484 0.2380 0.087 Uiso 1 1 calc R . .
C23 C -0.1261(6) 0.2874(3) 0.2698(2) 0.0778(19) Uani 1 1 d . . .
C5 C -0.0295(5) 0.6068(3) 0.4714(3) 0.0771(19) Uani 1 1 d . . .
C25 C -0.0897(5) 0.3390(3) 0.2582(2) 0.0690(17) Uani 1 1 d . . .
H25 H -0.0304 0.3449 0.2337 0.083 Uiso 1 1 calc R . .
C21 C -0.2159(6) 0.2789(3) 0.3081(2) 0.0758(17) Uani 1 1 d . . .
C4 C 0.0188(6) 0.6325(3) 0.5167(3) 0.0766(19) Uani 1 1 d . . .
C17 C -0.0384(5) 0.4660(3) 0.2498(2) 0.0748(18) Uani 1 1 d . . .
H17A H -0.0737 0.4958 0.2307 0.090 Uiso 1 1 calc R . .
H17B H -0.0039 0.4415 0.2242 0.090 Uiso 1 1 calc R . .
C10 C 0.1891(6) 0.4595(2) 0.4196(2) 0.0641(16) Uani 1 1 d . . .
H10A H 0.1268 0.4341 0.4271 0.077 Uiso 1 1 calc R . .
H10B H 0.2617 0.4393 0.4173 0.077 Uiso 1 1 calc R . .
C13 C 0.2036(7) 0.5540(3) 0.3029(2) 0.095(2) Uani 1 1 d . . .
H13 H 0.2449 0.5845 0.2922 0.114 Uiso 1 1 calc R . .
C22 C -0.2536(8) 0.2217(3) 0.3220(3) 0.114(3) Uani 1 1 d . . .
H22A H -0.1925 0.2041 0.3415 0.172 Uiso 1 1 calc R . .
H22B H -0.2688 0.2019 0.2900 0.172 Uiso 1 1 calc R . .
H22C H -0.3233 0.2230 0.3430 0.172 Uiso 1 1 calc R . .
C20 C -0.2671(5) 0.3218(3) 0.3332(2) 0.0671(16) Uani 1 1 d . . .
H20 H -0.3256 0.3161 0.3581 0.081 Uiso 1 1 calc R . .
C12 C 0.2271(6) 0.5311(3) 0.3504(2) 0.081(2) Uani 1 1 d . . .
H12 H 0.2854 0.5457 0.3717 0.098 Uiso 1 1 calc R . .
C9 C -0.0362(8) 0.6837(3) 0.5386(3) 0.123(3) Uani 1 1 d . . .
H9A H 0.0080 0.6960 0.5685 0.184 Uiso 1 1 calc R . .
H9B H -0.1151 0.6762 0.5493 0.184 Uiso 1 1 calc R . .
H9C H -0.0365 0.7112 0.5118 0.184 Uiso 1 1 calc R . .
C24 C -0.0718(8) 0.2395(3) 0.2406(3) 0.112(3) Uani 1 1 d . . .
H24A H 0.0007 0.2505 0.2248 0.168 Uiso 1 1 calc R . .
H24B H -0.1244 0.2273 0.2135 0.168 Uiso 1 1 calc R . .
H24C H -0.0576 0.2106 0.2651 0.168 Uiso 1 1 calc R . .
C8 C -0.1371(6) 0.6294(4) 0.4443(3) 0.121(3) Uani 1 1 d . . .
H8A H -0.1198 0.6647 0.4303 0.182 Uiso 1 1 calc R . .
H8B H -0.1998 0.6322 0.4694 0.182 Uiso 1 1 calc R . .
H8C H -0.1599 0.6058 0.4160 0.182 Uiso 1 1 calc R . .
O4 O 1.0629(4) 0.12562(15) 0.57373(14) 0.0656(10) Uani 1 1 d . . .
O3 O 0.9606(3) 0.08617(15) 0.63526(15) 0.0681(11) Uani 1 1 d . . .
N3 N -0.2683(4) 0.42448(18) 0.33970(16) 0.0564(11) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N1 2.072(4) . ?
Co1 N3 2.082(4) 5_566 ?
Co1 O4 2.104(4) 7_765 ?
Co1 O2 2.127(4) . ?
Co1 O3 2.230(4) 7_765 ?
Co1 O1 2.237(4) . ?
Co1 C40 2.502(5) 7_765 ?
Co1 C27 2.508(5) . ?
O2 C27 1.251(6) . ?
O1 C27 1.244(6) . ?
N1 C1 1.310(6) . ?
N1 C2 1.399(6) . ?
N2 C1 1.355(6) . ?
N2 C7 1.385(6) . ?
N2 C10 1.473(6) . ?
N4 C18 1.334(7) . ?
N4 C26 1.382(7) . ?
N4 C17 1.466(7) . ?
C37 C38 1.382(7) . ?
C37 C36 1.381(7) . ?
C37 C40 1.482(7) . ?
C31 C32 1.388(7) . ?
C31 C30 1.392(7) . ?
C31 C34 1.482(7) . ?
C40 O3 1.259(6) . ?
C40 O4 1.254(6) . ?
C40 Co1 2.502(5) 7_755 ?
C7 C6 1.393(7) . ?
C7 C2 1.391(7) . ?
C28 C29 1.371(6) . ?
C28 C33 1.371(7) . ?
C28 C27 1.505(7) . ?
C39 C34 1.395(7) . ?
C39 C38 1.392(7) . ?
C39 H39 0.9300 . ?
C38 H38 0.9300 . ?
C34 C35 1.387(7) . ?
C2 C3 1.388(7) . ?
C32 C33 1.385(7) . ?
C32 H32 0.9300 . ?
C29 C30 1.366(7) . ?
C29 H29 0.9300 . ?
C26 C25 1.374(8) . ?
C26 C19 1.402(7) . ?
C33 H33 0.9300 . ?
C3 C4 1.383(8) . ?
C3 H3 0.9300 . ?
C1 H1 0.9300 . ?
C11 C12 1.377(8) . ?
C11 C16 1.382(7) . ?
C11 C10 1.499(7) . ?
C18 N3 1.321(6) . ?
C18 H18 0.9300 . ?
C36 C35 1.371(8) . ?
C36 H36 0.9300 . ?
C35 H35 0.9300 . ?
C19 C20 1.382(7) . ?
C19 N3 1.406(6) . ?
C30 H30 0.9300 . ?
C6 C5 1.381(8) . ?
C6 H6 0.9300 . ?
C15 C16 1.378(7) . ?
C15 C14 1.380(8) . ?
C15 C17 1.510(7) . ?
C16 H16 0.9300 . ?
C14 C13 1.371(8) . ?
C14 H14 0.9300 . ?
C23 C25 1.373(9) . ?
C23 C21 1.427(9) . ?
C23 C24 1.526(9) . ?
C5 C4 1.421(9) . ?
C5 C8 1.516(9) . ?
C25 H25 0.9300 . ?
C21 C20 1.366(8) . ?
C21 C22 1.518(9) . ?
C4 C9 1.516(8) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C13 C12 1.354(8) . ?
C13 H13 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C20 H20 0.9300 . ?
C12 H12 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
O4 Co1 2.104(3) 7_755 ?
O3 Co1 2.230(4) 7_755 ?
N3 Co1 2.082(4) 5_566 ?

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
N1 Co1 N3 103.29(17) . 5_566 ?
N1 Co1 O4 95.19(15) . 7_765 ?
N3 Co1 O4 98.45(17) 5_566 7_765 ?
N1 Co1 O2 88.73(15) . . ?
N3 Co1 O2 149.80(17) 5_566 . ?
O4 Co1 O2 108.06(15) 7_765 . ?
N1 Co1 O3 151.61(15) . 7_765 ?
N3 Co1 O3 94.81(15) 5_566 7_765 ?
O4 Co1 O3 60.22(14) 7_765 7_765 ?
O2 Co1 O3 86.29(14) . 7_765 ?
N1 Co1 O1 100.89(16) . . ?
N3 Co1 O1 90.71(16) 5_566 . ?
O4 Co1 O1 159.17(16) 7_765 . ?
O2 Co1 O1 59.58(14) . . ?
O3 Co1 O1 100.56(15) 7_765 . ?
N1 Co1 C40 124.01(16) . 7_765 ?
N3 Co1 C40 97.80(17) 5_566 7_765 ?
O4 Co1 C40 30.05(15) 7_765 7_765 ?
O2 Co1 C40 98.05(16) . 7_765 ?
O3 Co1 C40 30.17(14) 7_765 7_765 ?
O1 Co1 C40 130.29(17) . 7_765 ?
N1 Co1 C27 96.06(16) . . ?
N3 Co1 C27 120.18(18) 5_566 . ?
O4 Co1 C27 135.66(18) 7_765 . ?
O2 Co1 C27 29.89(15) . . ?
O3 Co1 C27 93.42(16) 7_765 . ?
O1 Co1 C27 29.70(15) . . ?
C40 Co1 C27 116.56(18) 7_765 . ?
C27 O2 Co1 92.2(3) . . ?
C27 O1 Co1 87.3(3) . . ?
C1 N1 C2 104.7(4) . . ?
C1 N1 Co1 124.3(3) . . ?
C2 N1 Co1 130.9(3) . . ?
C1 N2 C7 106.3(4) . . ?
C1 N2 C10 125.3(4) . . ?
C7 N2 C10 128.4(4) . . ?
C18 N4 C26 107.4(5) . . ?
C18 N4 C17 125.5(5) . . ?
C26 N4 C17 126.6(5) . . ?
C38 C37 C36 118.7(5) . . ?
C38 C37 C40 121.7(5) . . ?
C36 C37 C40 119.6(5) . . ?
C32 C31 C30 116.7(5) . . ?
C32 C31 C34 122.1(4) . . ?
C30 C31 C34 121.1(5) . . ?
O3 C40 O4 120.1(5) . . ?
O3 C40 C37 119.8(5) . . ?
O4 C40 C37 120.2(5) . . ?
O3 C40 Co1 62.9(3) . 7_755 ?
O4 C40 Co1 57.1(3) . 7_755 ?
C37 C40 Co1 177.3(4) . 7_755 ?
N2 C7 C6 132.6(5) . . ?
N2 C7 C2 105.9(4) . . ?
C6 C7 C2 121.5(5) . . ?
C29 C28 C33 118.4(5) . . ?
C29 C28 C27 119.6(5) . . ?
C33 C28 C27 121.6(5) . . ?
O2 C27 O1 120.9(5) . . ?
O2 C27 C28 118.3(5) . . ?
O1 C27 C28 120.8(5) . . ?
O2 C27 Co1 57.9(3) . . ?
O1 C27 Co1 63.0(3) . . ?
C28 C27 Co1 174.9(4) . . ?
C34 C39 C38 120.2(5) . . ?
C34 C39 H39 119.9 . . ?
C38 C39 H39 119.9 . . ?
C37 C38 C39 120.9(5) . . ?
C37 C38 H38 119.5 . . ?
C39 C38 H38 119.5 . . ?
C35 C34 C39 117.8(5) . . ?
C35 C34 C31 121.1(5) . . ?
C39 C34 C31 121.1(5) . . ?
N1 C2 C7 109.3(4) . . ?
N1 C2 C3 130.1(5) . . ?
C7 C2 C3 120.6(5) . . ?
C33 C32 C31 121.1(5) . . ?
C33 C32 H32 119.4 . . ?
C31 C32 H32 119.4 . . ?
C28 C29 C30 121.2(5) . . ?
C28 C29 H29 119.4 . . ?
C30 C29 H29 119.4 . . ?
C25 C26 N4 132.8(6) . . ?
C25 C26 C19 121.7(6) . . ?
N4 C26 C19 105.5(5) . . ?
C28 C33 C32 120.9(5) . . ?
C28 C33 H33 119.6 . . ?
C32 C33 H33 119.6 . . ?
C4 C3 C2 118.5(6) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
N1 C1 N2 113.8(4) . . ?
N1 C1 H1 123.1 . . ?
N2 C1 H1 123.1 . . ?
C12 C11 C16 118.0(5) . . ?
C12 C11 C10 122.7(5) . . ?
C16 C11 C10 119.2(5) . . ?
N3 C18 N4 113.7(5) . . ?
N3 C18 H18 123.2 . . ?
N4 C18 H18 123.2 . . ?
C35 C36 C37 120.6(5) . . ?
C35 C36 H36 119.7 . . ?
C37 C36 H36 119.7 . . ?
C36 C35 C34 121.7(5) . . ?
C36 C35 H35 119.1 . . ?
C34 C35 H35 119.1 . . ?
C20 C19 C26 119.8(5) . . ?
C20 C19 N3 131.5(5) . . ?
C26 C19 N3 108.7(5) . . ?
C29 C30 C31 121.6(5) . . ?
C29 C30 H30 119.2 . . ?
C31 C30 H30 119.2 . . ?
C5 C6 C7 118.1(6) . . ?
C5 C6 H6 120.9 . . ?
C7 C6 H6 120.9 . . ?
C16 C15 C14 117.4(5) . . ?
C16 C15 C17 123.1(5) . . ?
C14 C15 C17 119.4(5) . . ?
C15 C16 C11 122.3(5) . . ?
C15 C16 H16 118.8 . . ?
C11 C16 H16 118.8 . . ?
C15 C14 C13 121.0(6) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C25 C23 C21 120.0(6) . . ?
C25 C23 C24 119.5(7) . . ?
C21 C23 C24 120.5(7) . . ?
C6 C5 C4 120.4(5) . . ?
C6 C5 C8 118.6(7) . . ?
C4 C5 C8 121.0(7) . . ?
C26 C25 C23 118.6(6) . . ?
C26 C25 H25 120.7 . . ?
C23 C25 H25 120.7 . . ?
C20 C21 C23 120.7(6) . . ?
C20 C21 C22 119.5(6) . . ?
C23 C21 C22 119.8(6) . . ?
C3 C4 C5 120.8(6) . . ?
C3 C4 C9 118.9(7) . . ?
C5 C4 C9 120.4(6) . . ?
N4 C17 C15 111.5(4) . . ?
N4 C17 H17A 109.3 . . ?
C15 C17 H17A 109.3 . . ?
N4 C17 H17B 109.3 . . ?
C15 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
N2 C10 C11 112.2(4) . . ?
N2 C10 H10A 109.2 . . ?
C11 C10 H10A 109.2 . . ?
N2 C10 H10B 109.2 . . ?
C11 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C12 C13 C14 120.3(6) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C20 C19 119.2(6) . . ?
C21 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C13 C12 C11 120.9(6) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C40 O4 Co1 92.8(3) . 7_755 ?
C40 O3 Co1 86.9(3) . 7_755 ?
C18 N3 C19 104.6(4) . . ?
C18 N3 Co1 120.0(4) . 5_566 ?
C19 N3 Co1 134.9(4) . 5_566 ?

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
N1 Co1 O2 C27 -104.5(3) . . . . ?
N3 Co1 O2 C27 10.3(5) 5_566 . . . ?
O4 Co1 O2 C27 160.4(3) 7_765 . . . ?
O3 Co1 O2 C27 103.5(3) 7_765 . . . ?
O1 Co1 O2 C27 -1.1(3) . . . . ?
C40 Co1 O2 C27 131.3(3) 7_765 . . . ?
N1 Co1 O1 C27 83.1(3) . . . . ?
N3 Co1 O1 C27 -173.2(3) 5_566 . . . ?
O4 Co1 O1 C27 -56.7(5) 7_765 . . . ?
O2 Co1 O1 C27 1.1(3) . . . . ?
O3 Co1 O1 C27 -78.2(3) 7_765 . . . ?
C40 Co1 O1 C27 -72.4(3) 7_765 . . . ?
N3 Co1 N1 C1 -146.3(4) 5_566 . . . ?
O4 Co1 N1 C1 113.8(4) 7_765 . . . ?
O2 Co1 N1 C1 5.8(4) . . . . ?
O3 Co1 N1 C1 85.6(5) 7_765 . . . ?
O1 Co1 N1 C1 -52.9(4) . . . . ?
C40 Co1 N1 C1 104.6(4) 7_765 . . . ?
C27 Co1 N1 C1 -23.3(4) . . . . ?
N3 Co1 N1 C2 37.6(4) 5_566 . . . ?
O4 Co1 N1 C2 -62.3(4) 7_765 . . . ?
O2 Co1 N1 C2 -170.4(4) . . . . ?
O3 Co1 N1 C2 -90.6(5) 7_765 . . . ?
O1 Co1 N1 C2 131.0(4) . . . . ?
C40 Co1 N1 C2 -71.5(5) 7_765 . . . ?
C27 Co1 N1 C2 160.6(4) . . . . ?
C38 C37 C40 O3 -1.7(7) . . . . ?
C36 C37 C40 O3 177.3(5) . . . . ?
C38 C37 C40 O4 178.5(5) . . . . ?
C36 C37 C40 O4 -2.5(8) . . . . ?
C38 C37 C40 Co1 174(8) . . . 7_755 ?
C36 C37 C40 Co1 -7(8) . . . 7_755 ?
C1 N2 C7 C6 -179.8(6) . . . . ?
C10 N2 C7 C6 -2.3(9) . . . . ?
C1 N2 C7 C2 0.9(5) . . . . ?
C10 N2 C7 C2 178.4(5) . . . . ?
Co1 O2 C27 O1 2.0(5) . . . . ?
Co1 O2 C27 C28 -176.0(4) . . . . ?
Co1 O1 C27 O2 -1.9(5) . . . . ?
Co1 O1 C27 C28 176.0(4) . . . . ?
C29 C28 C27 O2 -22.1(7) . . . . ?
C33 C28 C27 O2 151.1(5) . . . . ?
C29 C28 C27 O1 160.0(5) . . . . ?
C33 C28 C27 O1 -26.8(8) . . . . ?
C29 C28 C27 Co1 -64(4) . . . . ?
C33 C28 C27 Co1 109(4) . . . . ?
N1 Co1 C27 O2 76.7(3) . . . . ?
N3 Co1 C27 O2 -174.0(3) 5_566 . . . ?
O4 Co1 C27 O2 -27.1(4) 7_765 . . . ?
O3 Co1 C27 O2 -76.5(3) 7_765 . . . ?
O1 Co1 C27 O2 178.1(5) . . . . ?
C40 Co1 C27 O2 -56.3(3) 7_765 . . . ?
N1 Co1 C27 O1 -101.4(3) . . . . ?
N3 Co1 C27 O1 7.9(4) 5_566 . . . ?
O4 Co1 C27 O1 154.8(3) 7_765 . . . ?
O2 Co1 C27 O1 -178.1(5) . . . . ?
O3 Co1 C27 O1 105.4(3) 7_765 . . . ?
C40 Co1 C27 O1 125.6(3) 7_765 . . . ?
N1 Co1 C27 C28 120(4) . . . . ?
N3 Co1 C27 C28 -130(4) 5_566 . . . ?
O4 Co1 C27 C28 17(4) 7_765 . . . ?
O2 Co1 C27 C28 44(4) . . . . ?
O3 Co1 C27 C28 -33(4) 7_765 . . . ?
O1 Co1 C27 C28 -138(4) . . . . ?
C40 Co1 C27 C28 -13(4) 7_765 . . . ?
C36 C37 C38 C39 0.3(8) . . . . ?
C40 C37 C38 C39 179.3(4) . . . . ?
C34 C39 C38 C37 0.3(7) . . . . ?
C38 C39 C34 C35 -1.3(8) . . . . ?
C38 C39 C34 C31 178.9(4) . . . . ?
C32 C31 C34 C35 -144.6(6) . . . . ?
C30 C31 C34 C35 32.7(8) . . . . ?
C32 C31 C34 C39 35.2(7) . . . . ?
C30 C31 C34 C39 -147.4(5) . . . . ?
C1 N1 C2 C7 1.7(6) . . . . ?
Co1 N1 C2 C7 178.4(3) . . . . ?
C1 N1 C2 C3 -175.3(5) . . . . ?
Co1 N1 C2 C3 1.3(8) . . . . ?
N2 C7 C2 N1 -1.6(6) . . . . ?
C6 C7 C2 N1 179.0(5) . . . . ?
N2 C7 C2 C3 175.8(5) . . . . ?
C6 C7 C2 C3 -3.7(8) . . . . ?
C30 C31 C32 C33 -0.8(8) . . . . ?
C34 C31 C32 C33 176.6(5) . . . . ?
C33 C28 C29 C30 -1.5(8) . . . . ?
C27 C28 C29 C30 172.0(5) . . . . ?
C18 N4 C26 C25 -179.8(6) . . . . ?
C17 N4 C26 C25 -7.8(9) . . . . ?
C18 N4 C26 C19 0.8(6) . . . . ?
C17 N4 C26 C19 172.8(4) . . . . ?
C29 C28 C33 C32 3.1(8) . . . . ?
C27 C28 C33 C32 -170.2(5) . . . . ?
C31 C32 C33 C28 -1.9(8) . . . . ?
N1 C2 C3 C4 178.5(5) . . . . ?
C7 C2 C3 C4 1.8(8) . . . . ?
C2 N1 C1 N2 -1.2(6) . . . . ?
Co1 N1 C1 N2 -178.1(3) . . . . ?
C7 N2 C1 N1 0.2(6) . . . . ?
C10 N2 C1 N1 -177.4(5) . . . . ?
C26 N4 C18 N3 -1.3(6) . . . . ?
C17 N4 C18 N3 -173.4(4) . . . . ?
C38 C37 C36 C35 0.1(9) . . . . ?
C40 C37 C36 C35 -178.9(6) . . . . ?
C37 C36 C35 C34 -1.2(10) . . . . ?
C39 C34 C35 C36 1.8(9) . . . . ?
C31 C34 C35 C36 -178.4(6) . . . . ?
C25 C26 C19 C20 -0.8(8) . . . . ?
N4 C26 C19 C20 178.7(5) . . . . ?
C25 C26 C19 N3 -179.6(5) . . . . ?
N4 C26 C19 N3 -0.2(6) . . . . ?
C28 C29 C30 C31 -1.4(9) . . . . ?
C32 C31 C30 C29 2.5(8) . . . . ?
C34 C31 C30 C29 -175.0(5) . . . . ?
N2 C7 C6 C5 -176.6(5) . . . . ?
C2 C7 C6 C5 2.7(8) . . . . ?
C14 C15 C16 C11 -0.1(8) . . . . ?
C17 C15 C16 C11 -178.2(5) . . . . ?
C12 C11 C16 C15 -0.5(8) . . . . ?
C10 C11 C16 C15 -179.1(5) . . . . ?
C16 C15 C14 C13 0.0(9) . . . . ?
C17 C15 C14 C13 178.3(6) . . . . ?
C7 C6 C5 C4 0.1(9) . . . . ?
C7 C6 C5 C8 178.7(6) . . . . ?
N4 C26 C25 C23 -178.1(5) . . . . ?
C19 C26 C25 C23 1.2(8) . . . . ?
C21 C23 C25 C26 -1.0(8) . . . . ?
C24 C23 C25 C26 177.6(5) . . . . ?
C25 C23 C21 C20 0.5(9) . . . . ?
C24 C23 C21 C20 -178.0(6) . . . . ?
C25 C23 C21 C22 -178.4(6) . . . . ?
C24 C23 C21 C22 3.0(9) . . . . ?
C2 C3 C4 C5 0.9(8) . . . . ?
C2 C3 C4 C9 -179.1(5) . . . . ?
C6 C5 C4 C3 -1.9(9) . . . . ?
C8 C5 C4 C3 179.5(6) . . . . ?
C6 C5 C4 C9 178.2(6) . . . . ?
C8 C5 C4 C9 -0.4(9) . . . . ?
C18 N4 C17 C15 67.3(7) . . . . ?
C26 N4 C17 C15 -103.3(6) . . . . ?
C16 C15 C17 N4 24.8(8) . . . . ?
C14 C15 C17 N4 -153.3(5) . . . . ?
C1 N2 C10 C11 -135.3(5) . . . . ?
C7 N2 C10 C11 47.7(8) . . . . ?
C12 C11 C10 N2 47.3(8) . . . . ?
C16 C11 C10 N2 -134.2(5) . . . . ?
C15 C14 C13 C12 0.5(11) . . . . ?
C23 C21 C20 C19 -0.1(9) . . . . ?
C22 C21 C20 C19 178.8(6) . . . . ?
C26 C19 C20 C21 0.2(8) . . . . ?
N3 C19 C20 C21 178.8(5) . . . . ?
C14 C13 C12 C11 -1.1(11) . . . . ?
C16 C11 C12 C13 1.1(10) . . . . ?
C10 C11 C12 C13 179.6(6) . . . . ?
O3 C40 O4 Co1 0.5(5) . . . 7_755 ?
C37 C40 O4 Co1 -179.7(4) . . . 7_755 ?
O4 C40 O3 Co1 -0.4(5) . . . 7_755 ?
C37 C40 O3 Co1 179.8(4) . . . 7_755 ?
N4 C18 N3 C19 1.1(6) . . . . ?
N4 C18 N3 Co1 174.3(3) . . . 5_566 ?
C20 C19 N3 C18 -179.2(6) . . . . ?
C26 C19 N3 C18 -0.5(5) . . . . ?
C20 C19 N3 Co1 9.2(9) . . . 5_566 ?
C26 C19 N3 Co1 -172.1(4) . . . 5_566 ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.054
_database_code_depnum_ccdc_archive 'CCDC 1013905'
#######################################################################
#
#                 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_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H30 Co N4 O5'
_chemical_formula_weight         621.54

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 '
_symmetry_space_group_name_Hall  '-P 2ybc '

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

_cell_length_a                   10.5449(11)
_cell_length_b                   9.9472(10)
_cell_length_c                   28.910(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.8990(10)
_cell_angle_gamma                90.00
_cell_volume                     3021.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2628
_cell_measurement_theta_min      3.62
_cell_measurement_theta_max      23.36

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1292
_exptl_absorpt_coefficient_mu    0.616
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7236
_exptl_absorpt_correction_T_max  0.8132
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine--focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27229
_diffrn_reflns_av_R_equivalents  0.1011
_diffrn_reflns_av_sigmaI/netI    0.1048
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         27.48
_reflns_number_total             6908
_reflns_number_gt                3736
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1998)'
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL  (Bruker, 1999)'
_computing_publication_material  SHELXTL

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0463P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6908
_refine_ls_number_parameters     392
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1226
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1288
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.59471(4) 0.52700(5) 0.267100(14) 0.03018(14) Uani 1 1 d . . .
O1 O 0.5162(2) 0.6539(2) 0.21419(7) 0.0353(6) Uani 1 1 d . . .
O1W O 0.4227(2) 0.4165(2) 0.26285(8) 0.0382(6) Uani 1 1 d . . .
O3 O 0.3469(2) 0.9258(3) -0.16852(8) 0.0449(6) Uani 1 1 d . . .
O2 O 0.6171(2) 0.4749(2) 0.19260(7) 0.0408(6) Uani 1 1 d . . .
N2 N 0.9837(3) 0.6245(3) 0.26664(9) 0.0341(7) Uani 1 1 d . . .
N3 N 1.1562(2) 0.6972(3) 0.22464(9) 0.0322(7) Uani 1 1 d . . .
C2 C 0.5765(3) 0.5463(3) 0.09766(11) 0.0353(8) Uani 1 1 d . . .
H2 H 0.6144 0.4634 0.1044 0.042 Uiso 1 1 calc R . .
C18 C 0.9973(4) 0.8643(4) 0.36554(13) 0.0441(9) Uani 1 1 d . . .
C26 C 0.9906(3) 0.7448(4) 0.15706(12) 0.0429(9) Uani 1 1 d . . .
H26 H 0.9331 0.6779 0.1636 0.051 Uiso 1 1 calc R . .
N1 N 0.7728(3) 0.6445(3) 0.26790(9) 0.0358(7) Uani 1 1 d . . .
C17 C 1.0479(3) 0.7818(4) 0.33346(12) 0.0410(9) Uani 1 1 d . . .
H17 H 1.1354 0.7697 0.3335 0.049 Uiso 1 1 calc R . .
C34 C 1.1028(3) 0.5858(3) 0.24917(12) 0.0366(8) Uani 1 1 d . . .
H34A H 1.0889 0.5099 0.2283 0.044 Uiso 1 1 calc R . .
H34B H 1.1625 0.5584 0.2748 0.044 Uiso 1 1 calc R . .
C16 C 0.9643(3) 0.7178(3) 0.30119(11) 0.0326(8) Uani 1 1 d . . .
C9 C 0.3632(3) 0.8468(4) -0.07501(12) 0.0433(9) Uani 1 1 d . . .
H9 H 0.2849 0.8761 -0.0885 0.052 Uiso 1 1 calc R . .
C30 C 1.1878(3) 0.8638(3) 0.17652(11) 0.0318(8) Uani 1 1 d . . .
C11 C 0.5815(3) 0.8006(4) -0.08013(11) 0.0410(9) Uani 1 1 d . . .
H11 H 0.6525 0.7992 -0.0971 0.049 Uiso 1 1 calc R . .
C15 C 0.8662(3) 0.5860(4) 0.24861(11) 0.0367(8) Uani 1 1 d . . .
H15 H 0.8532 0.5237 0.2247 0.044 Uiso 1 1 calc R . .
C29 C 1.1647(3) 0.9480(3) 0.13864(11) 0.0373(9) Uani 1 1 d . . .
H29 H 1.2226 1.0148 0.1325 0.045 Uiso 1 1 calc R . .
C4 C 0.5025(3) 0.7127(4) 0.04076(11) 0.0360(8) Uani 1 1 d . . .
C5 C 0.4573(4) 0.7884(4) 0.07621(12) 0.0451(10) Uani 1 1 d . . .
H5 H 0.4153 0.8690 0.0692 0.054 Uiso 1 1 calc R . .
C3 C 0.5620(3) 0.5918(4) 0.05243(11) 0.0367(8) Uani 1 1 d . . .
H3 H 0.5930 0.5398 0.0292 0.044 Uiso 1 1 calc R . .
C6 C 0.4738(3) 0.7458(4) 0.12187(11) 0.0394(9) Uani 1 1 d . . .
H6 H 0.4441 0.7985 0.1452 0.047 Uiso 1 1 calc R . .
C20 C 0.7829(3) 0.8193(3) 0.33170(12) 0.0379(9) Uani 1 1 d . . .
H20 H 0.6955 0.8336 0.3303 0.046 Uiso 1 1 calc R . .
C13 C 0.4543(3) 0.8925(3) -0.15067(11) 0.0334(8) Uani 1 1 d . . .
C10 C 0.4663(3) 0.8450(3) -0.10098(11) 0.0323(8) Uani 1 1 d . . .
C25 C 1.1033(3) 0.7618(3) 0.18486(11) 0.0332(8) Uani 1 1 d . . .
C1 C 0.5343(3) 0.6246(3) 0.13307(11) 0.0303(8) Uani 1 1 d . . .
C28 C 1.0530(4) 0.9307(4) 0.10998(12) 0.0464(10) Uani 1 1 d . . .
C14 C 0.5562(3) 0.5801(4) 0.18231(11) 0.0333(8) Uani 1 1 d . . .
C7 C 0.4893(3) 0.7606(3) -0.00803(11) 0.0366(9) Uani 1 1 d . . .
C21 C 0.8331(3) 0.7306(3) 0.30116(11) 0.0335(8) Uani 1 1 d . . .
C8 C 0.3737(3) 0.8059(4) -0.02911(12) 0.0472(10) Uani 1 1 d . . .
H8 H 0.3026 0.8087 -0.0122 0.057 Uiso 1 1 calc R . .
C19 C 0.8633(4) 0.8866(4) 0.36427(13) 0.0432(9) Uani 1 1 d . . .
C23 C 0.8074(4) 0.9797(4) 0.39849(15) 0.0635(12) Uani 1 1 d . . .
H23A H 0.7165 0.9816 0.3925 0.095 Uiso 1 1 calc R . .
H23B H 0.8408 1.0687 0.3952 0.095 Uiso 1 1 calc R . .
H23C H 0.8295 0.9481 0.4295 0.095 Uiso 1 1 calc R . .
C27 C 0.9655(4) 0.8294(4) 0.11947(13) 0.0489(10) Uani 1 1 d . . .
C12 C 0.5927(3) 0.7584(4) -0.03460(12) 0.0420(9) Uani 1 1 d . . .
H12 H 0.6710 0.7280 -0.0214 0.050 Uiso 1 1 calc R . .
C22 C 1.0850(4) 0.9260(4) 0.40375(14) 0.0684(13) Uani 1 1 d . . .
H22A H 1.1718 0.9083 0.3980 0.103 Uiso 1 1 calc R . .
H22B H 1.0678 0.8876 0.4330 0.103 Uiso 1 1 calc R . .
H22C H 1.0712 1.0213 0.4045 0.103 Uiso 1 1 calc R . .
C32 C 0.8416(4) 0.8133(5) 0.08926(16) 0.0798(16) Uani 1 1 d . . .
H32A H 0.8596 0.7968 0.0578 0.120 Uiso 1 1 calc R . .
H32B H 0.7921 0.8940 0.0906 0.120 Uiso 1 1 calc R . .
H32C H 0.7946 0.7390 0.1003 0.120 Uiso 1 1 calc R . .
C31 C 1.0286(4) 1.0236(4) 0.06896(14) 0.0726(14) Uani 1 1 d . . .
H31A H 1.0952 1.0895 0.0694 0.109 Uiso 1 1 calc R . .
H31B H 0.9483 1.0680 0.0707 0.109 Uiso 1 1 calc R . .
H31C H 1.0268 0.9725 0.0407 0.109 Uiso 1 1 calc R . .
O4 O 0.5568(2) 0.8945(2) -0.17108(7) 0.0410(6) Uani 1 1 d . . .
C33 C 1.2657(3) 0.7637(3) 0.23840(11) 0.0323(8) Uani 1 1 d . . .
H33 H 1.3186 0.7401 0.2645 0.039 Uiso 1 1 calc R . .
N4 N 1.2890(2) 0.8637(3) 0.21137(9) 0.0302(6) Uani 1 1 d . . .
H1WA H 0.3772 0.4444 0.2824 0.045 Uiso 1 1 d R . .
H1WB H 0.4334 0.3377 0.2668 0.045 Uiso 1 1 d R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O4 2.021(2) 4_576 ?
Co1 N4 2.097(3) 2_745 ?
Co1 O1 2.098(2) . ?
Co1 O1W 2.116(2) . ?
Co1 N1 2.210(3) . ?
Co1 O2 2.247(2) . ?
Co1 C14 2.507(3) . ?
O1 C14 1.278(4) . ?
O1W H1WA 0.8203 . ?
O1W H1WB 0.7981 . ?
O3 C13 1.249(4) . ?
O2 C14 1.250(4) . ?
N2 C15 1.357(4) . ?
N2 C16 1.391(4) . ?
N2 C34 1.446(4) . ?
N3 C33 1.360(4) . ?
N3 C25 1.392(4) . ?
N3 C34 1.455(4) . ?
C2 C3 1.380(4) . ?
C2 C1 1.389(4) . ?
C2 H2 0.9300 . ?
C18 C17 1.379(5) . ?
C18 C19 1.428(5) . ?
C18 C22 1.509(5) . ?
C26 C27 1.381(5) . ?
C26 C25 1.387(4) . ?
C26 H26 0.9300 . ?
N1 C15 1.309(4) . ?
N1 C21 1.399(4) . ?
C17 C16 1.383(4) . ?
C17 H17 0.9300 . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C16 C21 1.390(4) . ?
C9 C10 1.372(4) . ?
C9 C8 1.383(4) . ?
C9 H9 0.9300 . ?
C30 C29 1.384(4) . ?
C30 C25 1.385(4) . ?
C30 N4 1.404(4) . ?
C11 C12 1.377(4) . ?
C11 C10 1.381(4) . ?
C11 H11 0.9300 . ?
C15 H15 0.9300 . ?
C29 C28 1.392(5) . ?
C29 H29 0.9300 . ?
C4 C3 1.385(4) . ?
C4 C5 1.388(5) . ?
C4 C7 1.484(4) . ?
C5 C6 1.383(4) . ?
C5 H5 0.9300 . ?
C3 H3 0.9300 . ?
C6 C1 1.389(4) . ?
C6 H6 0.9300 . ?
C20 C19 1.385(5) . ?
C20 C21 1.385(4) . ?
C20 H20 0.9300 . ?
C13 O4 1.274(4) . ?
C13 C10 1.507(4) . ?
C1 C14 1.490(4) . ?
C28 C27 1.409(5) . ?
C28 C31 1.508(5) . ?
C7 C12 1.386(5) . ?
C7 C8 1.390(5) . ?
C8 H8 0.9300 . ?
C19 C23 1.511(5) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C27 C32 1.517(5) . ?
C12 H12 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
O4 Co1 2.021(2) 4_575 ?
C33 N4 1.302(4) . ?
C33 H33 0.9300 . ?
N4 Co1 2.097(3) 2_755 ?

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
O4 Co1 N4 101.04(10) 4_576 2_745 ?
O4 Co1 O1 108.47(9) 4_576 . ?
N4 Co1 O1 150.06(9) 2_745 . ?
O4 Co1 O1W 91.06(9) 4_576 . ?
N4 Co1 O1W 95.24(9) 2_745 . ?
O1 Co1 O1W 89.28(9) . . ?
O4 Co1 N1 91.07(10) 4_576 . ?
N4 Co1 N1 86.09(10) 2_745 . ?
O1 Co1 N1 88.36(9) . . ?
O1W Co1 N1 177.22(9) . . ?
O4 Co1 O2 168.95(9) 4_576 . ?
N4 Co1 O2 89.95(9) 2_745 . ?
O1 Co1 O2 60.48(8) . . ?
O1W Co1 O2 89.10(9) . . ?
N1 Co1 O2 88.46(9) . . ?
O4 Co1 C14 139.08(11) 4_576 . ?
N4 Co1 C14 119.69(11) 2_745 . ?
O1 Co1 C14 30.61(9) . . ?
O1W Co1 C14 89.20(9) . . ?
N1 Co1 C14 88.02(10) . . ?
O2 Co1 C14 29.87(9) . . ?
C14 O1 Co1 92.66(19) . . ?
Co1 O1W H1WA 109.5 . . ?
Co1 O1W H1WB 113.0 . . ?
H1WA O1W H1WB 108.6 . . ?
C14 O2 Co1 86.62(19) . . ?
C15 N2 C16 106.2(3) . . ?
C15 N2 C34 125.7(3) . . ?
C16 N2 C34 127.8(3) . . ?
C33 N3 C25 106.7(3) . . ?
C33 N3 C34 125.6(3) . . ?
C25 N3 C34 127.6(3) . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C17 C18 C19 120.9(3) . . ?
C17 C18 C22 119.1(3) . . ?
C19 C18 C22 119.9(3) . . ?
C27 C26 C25 118.6(3) . . ?
C27 C26 H26 120.7 . . ?
C25 C26 H26 120.7 . . ?
C15 N1 C21 104.5(3) . . ?
C15 N1 Co1 115.5(2) . . ?
C21 N1 Co1 131.8(2) . . ?
C18 C17 C16 117.8(3) . . ?
C18 C17 H17 121.1 . . ?
C16 C17 H17 121.1 . . ?
N2 C34 N3 110.6(3) . . ?
N2 C34 H34A 109.5 . . ?
N3 C34 H34A 109.5 . . ?
N2 C34 H34B 109.5 . . ?
N3 C34 H34B 109.5 . . ?
H34A C34 H34B 108.1 . . ?
C17 C16 C21 122.4(3) . . ?
C17 C16 N2 131.9(3) . . ?
C21 C16 N2 105.5(3) . . ?
C10 C9 C8 121.3(3) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C29 C30 C25 120.6(3) . . ?
C29 C30 N4 129.8(3) . . ?
C25 C30 N4 109.6(3) . . ?
C12 C11 C10 121.0(3) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
N1 C15 N2 114.0(3) . . ?
N1 C15 H15 123.0 . . ?
N2 C15 H15 123.0 . . ?
C30 C29 C28 118.7(3) . . ?
C30 C29 H29 120.7 . . ?
C28 C29 H29 120.7 . . ?
C3 C4 C5 117.9(3) . . ?
C3 C4 C7 120.9(3) . . ?
C5 C4 C7 121.2(3) . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C2 C3 C4 121.8(3) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C6 C1 120.4(3) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C19 C20 C21 119.8(3) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
O3 C13 O4 125.4(3) . . ?
O3 C13 C10 118.4(3) . . ?
O4 C13 C10 116.2(3) . . ?
C9 C10 C11 118.2(3) . . ?
C9 C10 C13 120.8(3) . . ?
C11 C10 C13 121.0(3) . . ?
C30 C25 C26 121.4(3) . . ?
C30 C25 N3 105.2(3) . . ?
C26 C25 N3 133.3(3) . . ?
C2 C1 C6 119.0(3) . . ?
C2 C1 C14 120.3(3) . . ?
C6 C1 C14 120.7(3) . . ?
C29 C28 C27 120.5(3) . . ?
C29 C28 C31 118.1(3) . . ?
C27 C28 C31 121.4(3) . . ?
O2 C14 O1 120.2(3) . . ?
O2 C14 C1 120.7(3) . . ?
O1 C14 C1 119.0(3) . . ?
O2 C14 Co1 63.52(17) . . ?
O1 C14 Co1 56.73(16) . . ?
C1 C14 Co1 174.8(3) . . ?
C12 C7 C8 117.6(3) . . ?
C12 C7 C4 120.5(3) . . ?
C8 C7 C4 121.9(3) . . ?
C20 C21 C16 119.5(3) . . ?
C20 C21 N1 130.7(3) . . ?
C16 C21 N1 109.8(3) . . ?
C9 C8 C7 120.7(3) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C20 C19 C18 119.3(3) . . ?
C20 C19 C23 119.4(3) . . ?
C18 C19 C23 121.3(3) . . ?
C19 C23 H23A 109.5 . . ?
C19 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C19 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C26 C27 C28 120.3(3) . . ?
C26 C27 C32 119.1(4) . . ?
C28 C27 C32 120.6(4) . . ?
C11 C12 C7 121.2(3) . . ?
C11 C12 H12 119.4 . . ?
C7 C12 H12 119.4 . . ?
C18 C22 H22A 109.5 . . ?
C18 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C18 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C27 C32 H32A 109.5 . . ?
C27 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C27 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C13 O4 Co1 130.9(2) . 4_575 ?
N4 C33 N3 113.3(3) . . ?
N4 C33 H33 123.4 . . ?
N3 C33 H33 123.4 . . ?
C33 N4 C30 105.1(3) . . ?
C33 N4 Co1 123.3(2) . 2_755 ?
C30 N4 Co1 127.0(2) . 2_755 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.070
_database_code_depnum_ccdc_archive 'CCDC 1013906'
