# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1401544'
_audit_update_record             
;
2015-05-17 deposited with the CCDC.
2015-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C54 H46 Co3 N6 O18'
_chemical_formula_weight         1243.76

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'
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_H-M   p21/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                   11.2930(14)
_cell_length_b                   12.7554(15)
_cell_length_c                   19.524(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.01
_cell_angle_gamma                90.00
_cell_volume                     2812.4(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1274
_exptl_absorpt_coefficient_mu    0.952
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18569
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         27.64
_reflns_number_total             6527
_reflns_number_gt                5631
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0494P)²+1.8131P] 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         6527
_refine_ls_number_parameters     367
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0999
_refine_ls_wR_factor_gt          0.0956
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.65230(2) 0.362866(19) 0.225914(12) 0.02125(8) Uani 1 1 d . . .
Co2 Co 1.0000 1.0000 0.0000 0.02308(9) Uani 1 2 d S . .
O1 O 0.65845(12) 0.51768(11) 0.26801(7) 0.0290(3) Uani 1 1 d . . .
H1A H 0.5797 0.5292 0.2731 0.044 Uiso 1 1 d R . .
H1B H 0.6836 0.5150 0.3074 0.044 Uiso 1 1 d R . .
O2 O 0.65454(12) 0.20984(11) 0.18007(7) 0.0303(3) Uani 1 1 d . . .
H2A H 0.7228 0.1939 0.1703 0.045 Uiso 1 1 d R . .
H2B H 0.6294 0.1552 0.2017 0.045 Uiso 1 1 d R . .
O3 O 0.99713(13) 1.04256(11) 0.10593(7) 0.0316(3) Uani 1 1 d . . .
H3A H 1.0652 1.0470 0.1203 0.047 Uiso 1 1 d R . .
H3B H 0.9623 1.0909 0.1252 0.047 Uiso 1 1 d R . .
O4 O 0.83448(13) 0.36608(12) 0.22246(8) 0.0361(3) Uani 1 1 d . . .
O5 O 0.88961(13) 0.22233(14) 0.16579(10) 0.0472(4) Uani 1 1 d . . .
O6 O 0.47385(12) 0.36627(11) 0.22334(8) 0.0336(3) Uani 1 1 d . . .
O7 O 0.42220(14) 0.52713(14) 0.25550(11) 0.0511(5) Uani 1 1 d . . .
O8 O 0.82102(12) 1.03170(13) -0.00616(8) 0.0345(3) Uani 1 1 d . . .
O9 O 0.76693(13) 0.95957(15) -0.10551(8) 0.0427(4) Uani 1 1 d . . .
N1 N 0.66478(17) 0.42913(14) 0.12409(8) 0.0332(4) Uani 1 1 d . . .
N2 N 0.65180(17) 0.28976(14) 0.32481(9) 0.0353(4) Uani 1 1 d . . .
N3 N 0.95115(17) 0.84516(14) 0.03109(10) 0.0358(4) Uani 1 1 d . . .
C1 C 0.39878(17) 0.43680(16) 0.23503(10) 0.0293(4) Uani 1 1 d . . .
C2 C 0.27194(17) 0.40575(17) 0.22301(11) 0.0313(4) Uani 1 1 d . . .
C3 C 0.2464(2) 0.3059(2) 0.19995(18) 0.0590(8) Uani 1 1 d . . .
H3 H 0.3078 0.2592 0.1910 0.071 Uiso 1 1 calc R . .
C4 C 0.1304(2) 0.2747(2) 0.19005(18) 0.0619(9) Uani 1 1 d . . .
H4 H 0.1147 0.2075 0.1738 0.074 Uiso 1 1 calc R . .
C5 C 0.03762(18) 0.34195(17) 0.20395(11) 0.0327(4) Uani 1 1 d . . .
C6 C 0.06303(19) 0.44217(19) 0.22702(15) 0.0458(6) Uani 1 1 d . . .
H6 H 0.0016 0.4886 0.2364 0.055 Uiso 1 1 calc R . .
C7 C 0.1794(2) 0.47371(19) 0.23618(15) 0.0464(6) Uani 1 1 d . . .
H7 H 0.1954 0.5414 0.2514 0.056 Uiso 1 1 calc R . .
C8 C 0.91139(17) 0.30716(17) 0.19615(11) 0.0317(4) Uani 1 1 d . . .
C9 C 0.6401(2) 0.37362(16) 0.06798(11) 0.0368(5) Uani 1 1 d . . .
H9 H 0.5954 0.3127 0.0725 0.044 Uiso 1 1 calc R . .
C10 C 0.6783(2) 0.40296(18) 0.00301(11) 0.0415(5) Uani 1 1 d . . .
C11 C 0.7410(3) 0.49610(19) -0.00355(12) 0.0493(7) Uani 1 1 d . . .
H11 H 0.7663 0.5185 -0.0465 0.059 Uiso 1 1 calc R . .
C12 C 0.7658(2) 0.55574(17) 0.05432(11) 0.0416(5) Uani 1 1 d . . .
C13 C 0.7266(2) 0.51819(17) 0.11710(11) 0.0373(5) Uani 1 1 d . . .
H13 H 0.7441 0.5567 0.1562 0.045 Uiso 1 1 calc R . .
C14 C 0.6644(2) 0.33406(18) -0.05759(11) 0.0412(5) Uani 1 1 d . . .
C15 C 0.5628(3) 0.2936(4) -0.07961(19) 0.0951(16) Uani 1 1 d . . .
H15 H 0.4933 0.3055 -0.0552 0.114 Uiso 1 1 calc R . .
C16 C 0.5603(3) 0.2664(4) 0.36098(19) 0.0926(15) Uani 1 1 d . . .
H16 H 0.4872 0.2914 0.3463 0.111 Uiso 1 1 calc R . .
C17 C 0.7521(3) 0.2582(4) 0.3498(2) 0.1040(18) Uani 1 1 d . . .
H17 H 0.8213 0.2791 0.3280 0.125 Uiso 1 1 calc R . .
C18 C 0.7617(3) 0.3047(4) -0.0930(2) 0.1117(19) Uani 1 1 d . . .
H18 H 0.8360 0.3272 -0.0787 0.134 Uiso 1 1 calc R . .
C19 C 0.8336(2) 0.65487(17) 0.04879(11) 0.0417(6) Uani 1 1 d . . .
C20 C 0.9224(3) 0.66640(19) 0.00035(14) 0.0510(7) Uani 1 1 d . . .
H20 H 0.9441 0.6100 -0.0271 0.061 Uiso 1 1 calc R . .
C21 C 0.9784(2) 0.76191(19) -0.00692(13) 0.0464(6) Uani 1 1 d . . .
H21 H 1.0377 0.7684 -0.0397 0.056 Uiso 1 1 calc R . .
C22 C 0.8693(3) 0.83290(19) 0.08019(13) 0.0457(6) Uani 1 1 d . . .
H22 H 0.8522 0.8896 0.1085 0.055 Uiso 1 1 calc R . .
C23 C 0.8093(3) 0.73987(19) 0.09066(13) 0.0480(6) Uani 1 1 d . . .
H23 H 0.7532 0.7344 0.1254 0.058 Uiso 1 1 calc R . .
C24 C 0.74450(17) 0.99686(16) -0.04744(10) 0.0296(4) Uani 1 1 d . . .
C25 C 0.61782(17) 0.99830(17) -0.02287(11) 0.0311(4) Uani 1 1 d . . .
C26 C 0.58716(19) 1.0497(2) 0.03752(11) 0.0407(5) Uani 1 1 d . . .
H26 H 0.6455 1.0834 0.0629 0.049 Uiso 1 1 calc R . .
C27 C 0.52895(19) 0.9486(2) -0.06019(11) 0.0402(5) Uani 1 1 d . . .
H27 H 0.5478 0.9140 -0.1007 0.048 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 O6 2.0163(14) . ?
Co1 O4 2.0589(15) . ?
Co1 O1 2.1400(14) . ?
Co1 N2 2.1442(17) . ?
Co1 O2 2.1475(14) . ?
Co1 N1 2.1648(17) . ?
Co2 O8 2.0648(14) . ?
Co2 O8 2.0648(14) 3_775 ?
Co2 O3 2.1384(14) . ?
Co2 O3 2.1384(14) 3_775 ?
Co2 N3 2.1386(17) . ?
Co2 N3 2.1387(17) 3_775 ?
O1 H1A 0.9067 . ?
O1 H1B 0.8200 . ?
O2 H2A 0.8201 . ?
O2 H2B 0.8630 . ?
O3 H3A 0.8200 . ?
O3 H3B 0.8223 . ?
O4 C8 1.258(2) . ?
O5 C8 1.258(3) . ?
O6 C1 1.257(2) . ?
O7 C1 1.248(3) . ?
O8 C24 1.262(2) . ?
O9 C24 1.255(3) . ?
N1 C9 1.334(3) . ?
N1 C13 1.340(3) . ?
N2 C16 1.287(4) . ?
N2 C17 1.297(4) . ?
N3 C21 1.332(3) . ?
N3 C22 1.340(3) . ?
C1 C2 1.505(3) . ?
C2 C3 1.382(3) . ?
C2 C7 1.382(3) . ?
C3 C4 1.383(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(3) . ?
C5 C8 1.501(3) 1_455 ?
C6 C7 1.386(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C5 1.501(3) 1_655 ?
C9 C10 1.391(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.389(3) . ?
C10 C14 1.482(3) . ?
C11 C12 1.391(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.388(3) . ?
C12 C19 1.483(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.329(4) . ?
C14 C18 1.351(5) . ?
C15 C16 1.390(4) 4_565 ?
C15 H15 0.9300 . ?
C16 C15 1.390(4) 4_566 ?
C16 H16 0.9300 . ?
C17 C18 1.379(4) 4_566 ?
C17 H17 0.9300 . ?
C18 C17 1.379(4) 4_565 ?
C18 H18 0.9300 . ?
C19 C23 1.386(3) . ?
C19 C20 1.386(3) . ?
C20 C21 1.380(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.382(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 C25 1.509(3) . ?
C25 C27 1.393(3) . ?
C25 C26 1.393(3) . ?
C26 C27 1.384(3) 3_675 ?
C26 H26 0.9300 . ?
C27 C26 1.384(3) 3_675 ?
C27 H27 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
O6 Co1 O4 175.93(6) . . ?
O6 Co1 O1 91.27(6) . . ?
O4 Co1 O1 87.81(6) . . ?
O6 Co1 N2 91.67(7) . . ?
O4 Co1 N2 92.34(7) . . ?
O1 Co1 N2 93.18(6) . . ?
O6 Co1 O2 91.20(6) . . ?
O4 Co1 O2 89.58(6) . . ?
O1 Co1 O2 176.75(5) . . ?
N2 Co1 O2 88.86(6) . . ?
O6 Co1 N1 91.94(7) . . ?
O4 Co1 N1 84.09(7) . . ?
O1 Co1 N1 89.44(6) . . ?
N2 Co1 N1 175.49(7) . . ?
O2 Co1 N1 88.36(6) . . ?
O8 Co2 O8 180.0 . 3_775 ?
O8 Co2 O3 89.53(6) . . ?
O8 Co2 O3 90.47(6) 3_775 . ?
O8 Co2 O3 90.47(6) . 3_775 ?
O8 Co2 O3 89.53(6) 3_775 3_775 ?
O3 Co2 O3 180.000(19) . 3_775 ?
O8 Co2 N3 86.84(7) . . ?
O8 Co2 N3 93.16(7) 3_775 . ?
O3 Co2 N3 87.48(6) . . ?
O3 Co2 N3 92.52(6) 3_775 . ?
O8 Co2 N3 93.16(7) . 3_775 ?
O8 Co2 N3 86.84(7) 3_775 3_775 ?
O3 Co2 N3 92.52(6) . 3_775 ?
O3 Co2 N3 87.48(6) 3_775 3_775 ?
N3 Co2 N3 180.00(10) . 3_775 ?
Co1 O1 H1A 99.2 . . ?
Co1 O1 H1B 109.5 . . ?
H1A O1 H1B 104.1 . . ?
Co1 O2 H2A 109.5 . . ?
Co1 O2 H2B 121.8 . . ?
H2A O2 H2B 102.9 . . ?
Co2 O3 H3A 109.5 . . ?
Co2 O3 H3B 129.9 . . ?
H3A O3 H3B 103.9 . . ?
C8 O4 Co1 133.74(13) . . ?
C1 O6 Co1 133.23(13) . . ?
C24 O8 Co2 129.67(13) . . ?
C9 N1 C13 118.37(18) . . ?
C9 N1 Co1 122.23(14) . . ?
C13 N1 Co1 117.29(14) . . ?
C16 N2 C17 115.0(2) . . ?
C16 N2 Co1 126.66(18) . . ?
C17 N2 Co1 118.1(2) . . ?
C21 N3 C22 117.70(19) . . ?
C21 N3 Co2 121.24(15) . . ?
C22 N3 Co2 119.24(15) . . ?
O7 C1 O6 125.17(18) . . ?
O7 C1 C2 119.65(18) . . ?
O6 C1 C2 115.18(18) . . ?
C3 C2 C7 118.8(2) . . ?
C3 C2 C1 119.48(19) . . ?
C7 C2 C1 121.74(19) . . ?
C2 C3 C4 120.6(2) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 118.7(2) . . ?
C4 C5 C8 121.1(2) . 1_455 ?
C6 C5 C8 120.17(19) . 1_455 ?
C5 C6 C7 120.4(2) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C2 C7 C6 120.7(2) . . ?
C2 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
O5 C8 O4 124.83(19) . . ?
O5 C8 C5 119.20(18) . 1_655 ?
O4 C8 C5 115.96(18) . 1_655 ?
N1 C9 C10 122.75(19) . . ?
N1 C9 H9 118.6 . . ?
C10 C9 H9 118.6 . . ?
C11 C10 C9 118.2(2) . . ?
C11 C10 C14 119.2(2) . . ?
C9 C10 C14 122.4(2) . . ?
C10 C11 C12 119.7(2) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C13 C12 C11 117.7(2) . . ?
C13 C12 C19 121.6(2) . . ?
C11 C12 C19 120.8(2) . . ?
N1 C13 C12 123.25(19) . . ?
N1 C13 H13 118.4 . . ?
C12 C13 H13 118.4 . . ?
C15 C14 C18 115.4(3) . . ?
C15 C14 C10 125.4(3) . . ?
C18 C14 C10 119.1(3) . . ?
C14 C15 C16 120.1(3) . 4_565 ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 4_565 . ?
N2 C16 C15 124.7(3) . 4_566 ?
N2 C16 H16 117.7 . . ?
C15 C16 H16 117.7 4_566 . ?
N2 C17 C18 123.7(3) . 4_566 ?
N2 C17 H17 118.2 . . ?
C18 C17 H17 118.2 4_566 . ?
C14 C18 C17 120.7(3) . 4_565 ?
C14 C18 H18 119.6 . . ?
C17 C18 H18 119.6 4_565 . ?
C23 C19 C20 117.6(2) . . ?
C23 C19 C12 121.5(2) . . ?
C20 C19 C12 120.9(2) . . ?
C21 C20 C19 119.7(2) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
N3 C21 C20 122.7(2) . . ?
N3 C21 H21 118.6 . . ?
C20 C21 H21 118.6 . . ?
N3 C22 C23 123.0(2) . . ?
N3 C22 H22 118.5 . . ?
C23 C22 H22 118.5 . . ?
C22 C23 C19 119.2(2) . . ?
C22 C23 H23 120.4 . . ?
C19 C23 H23 120.4 . . ?
O9 C24 O8 124.88(18) . . ?
O9 C24 C25 118.88(18) . . ?
O8 C24 C25 116.22(18) . . ?
C27 C25 C26 118.56(19) . . ?
C27 C25 C24 120.75(19) . . ?
C26 C25 C24 120.69(18) . . ?
C27 C26 C25 120.9(2) 3_675 . ?
C27 C26 H26 119.5 3_675 . ?
C25 C26 H26 119.5 . . ?
C26 C27 C25 120.5(2) 3_675 . ?
C26 C27 H27 119.7 3_675 . ?
C25 C27 H27 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O6 Co1 O4 C8 -93.4(9) . . . . ?
O1 Co1 O4 C8 -170.4(2) . . . . ?
N2 Co1 O4 C8 96.5(2) . . . . ?
O2 Co1 O4 C8 7.6(2) . . . . ?
N1 Co1 O4 C8 -80.8(2) . . . . ?
O4 Co1 O6 C1 -70.1(9) . . . . ?
O1 Co1 O6 C1 6.7(2) . . . . ?
N2 Co1 O6 C1 100.0(2) . . . . ?
O2 Co1 O6 C1 -171.14(19) . . . . ?
N1 Co1 O6 C1 -82.7(2) . . . . ?
O8 Co2 O8 C24 32(13) 3_775 . . . ?
O3 Co2 O8 C24 -155.71(19) . . . . ?
O3 Co2 O8 C24 24.29(19) 3_775 . . . ?
N3 Co2 O8 C24 -68.21(19) . . . . ?
N3 Co2 O8 C24 111.79(19) 3_775 . . . ?
O6 Co1 N1 C9 -73.77(19) . . . . ?
O4 Co1 N1 C9 107.12(19) . . . . ?
O1 Co1 N1 C9 -165.03(19) . . . . ?
N2 Co1 N1 C9 69.3(9) . . . . ?
O2 Co1 N1 C9 17.37(19) . . . . ?
O6 Co1 N1 C13 123.04(18) . . . . ?
O4 Co1 N1 C13 -56.07(18) . . . . ?
O1 Co1 N1 C13 31.79(18) . . . . ?
N2 Co1 N1 C13 -93.8(9) . . . . ?
O2 Co1 N1 C13 -145.82(18) . . . . ?
O6 Co1 N2 C16 -1.6(3) . . . . ?
O4 Co1 N2 C16 177.7(3) . . . . ?
O1 Co1 N2 C16 89.7(3) . . . . ?
O2 Co1 N2 C16 -92.8(3) . . . . ?
N1 Co1 N2 C16 -144.8(8) . . . . ?
O6 Co1 N2 C17 172.9(3) . . . . ?
O4 Co1 N2 C17 -7.8(3) . . . . ?
O1 Co1 N2 C17 -95.7(3) . . . . ?
O2 Co1 N2 C17 81.8(3) . . . . ?
N1 Co1 N2 C17 29.8(10) . . . . ?
O8 Co2 N3 C21 116.3(2) . . . . ?
O8 Co2 N3 C21 -63.7(2) 3_775 . . . ?
O3 Co2 N3 C21 -154.0(2) . . . . ?
O3 Co2 N3 C21 26.0(2) 3_775 . . . ?
N3 Co2 N3 C21 71(99) 3_775 . . . ?
O8 Co2 N3 C22 -48.0(2) . . . . ?
O8 Co2 N3 C22 132.0(2) 3_775 . . . ?
O3 Co2 N3 C22 41.7(2) . . . . ?
O3 Co2 N3 C22 -138.3(2) 3_775 . . . ?
N3 Co2 N3 C22 -94(89) 3_775 . . . ?
Co1 O6 C1 O7 -3.5(3) . . . . ?
Co1 O6 C1 C2 176.84(14) . . . . ?
O7 C1 C2 C3 179.6(3) . . . . ?
O6 C1 C2 C3 -0.8(3) . . . . ?
O7 C1 C2 C7 -2.2(3) . . . . ?
O6 C1 C2 C7 177.5(2) . . . . ?
C7 C2 C3 C4 0.2(5) . . . . ?
C1 C2 C3 C4 178.5(3) . . . . ?
C2 C3 C4 C5 -1.0(5) . . . . ?
C3 C4 C5 C6 1.0(5) . . . . ?
C3 C4 C5 C8 -177.4(3) . . . 1_455 ?
C4 C5 C6 C7 -0.3(4) . . . . ?
C8 C5 C6 C7 178.2(2) 1_455 . . . ?
C3 C2 C7 C6 0.5(4) . . . . ?
C1 C2 C7 C6 -177.7(2) . . . . ?
C5 C6 C7 C2 -0.5(4) . . . . ?
Co1 O4 C8 O5 -3.7(4) . . . . ?
Co1 O4 C8 C5 177.74(15) . . . 1_655 ?
C13 N1 C9 C10 1.7(4) . . . . ?
Co1 N1 C9 C10 -161.3(2) . . . . ?
N1 C9 C10 C11 -2.5(4) . . . . ?
N1 C9 C10 C14 171.7(2) . . . . ?
C9 C10 C11 C12 1.3(4) . . . . ?
C14 C10 C11 C12 -173.0(3) . . . . ?
C10 C11 C12 C13 0.5(4) . . . . ?
C10 C11 C12 C19 179.4(3) . . . . ?
C9 N1 C13 C12 0.3(4) . . . . ?
Co1 N1 C13 C12 164.1(2) . . . . ?
C11 C12 C13 N1 -1.3(4) . . . . ?
C19 C12 C13 N1 179.8(2) . . . . ?
C11 C10 C14 C15 -130.2(4) . . . . ?
C9 C10 C14 C15 55.7(5) . . . . ?
C11 C10 C14 C18 52.7(5) . . . . ?
C9 C10 C14 C18 -121.4(4) . . . . ?
C18 C14 C15 C16 -5.6(7) . . . 4_565 ?
C10 C14 C15 C16 177.2(4) . . . 4_565 ?
C17 N2 C16 C15 -3.9(7) . . . 4_566 ?
Co1 N2 C16 C15 170.8(4) . . . 4_566 ?
C16 N2 C17 C18 6.3(8) . . . 4_566 ?
Co1 N2 C17 C18 -168.9(5) . . . 4_566 ?
C15 C14 C18 C17 3.5(8) . . . 4_565 ?
C10 C14 C18 C17 -179.1(4) . . . 4_565 ?
C13 C12 C19 C23 -36.1(4) . . . . ?
C11 C12 C19 C23 145.0(3) . . . . ?
C13 C12 C19 C20 145.2(3) . . . . ?
C11 C12 C19 C20 -33.6(4) . . . . ?
C23 C19 C20 C21 -3.3(4) . . . . ?
C12 C19 C20 C21 175.4(3) . . . . ?
C22 N3 C21 C20 3.0(4) . . . . ?
Co2 N3 C21 C20 -161.5(2) . . . . ?
C19 C20 C21 N3 0.1(5) . . . . ?
C21 N3 C22 C23 -3.0(4) . . . . ?
Co2 N3 C22 C23 161.9(2) . . . . ?
N3 C22 C23 C19 -0.2(5) . . . . ?
C20 C19 C23 C22 3.3(4) . . . . ?
C12 C19 C23 C22 -175.4(3) . . . . ?
Co2 O8 C24 O9 -22.3(3) . . . . ?
Co2 O8 C24 C25 155.81(14) . . . . ?
O9 C24 C25 C27 7.3(3) . . . . ?
O8 C24 C25 C27 -171.0(2) . . . . ?
O9 C24 C25 C26 -172.5(2) . . . . ?
O8 C24 C25 C26 9.2(3) . . . . ?
C27 C25 C26 C27 0.1(4) . . . 3_675 ?
C24 C25 C26 C27 179.9(2) . . . 3_675 ?
C26 C25 C27 C26 -0.1(4) . . . 3_675 ?
C24 C25 C27 C26 -179.9(2) . . . 3_675 ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.64
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.744
_refine_diff_density_min         -0.592
_refine_diff_density_rms         0.064
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3
_database_code_depnum_ccdc_archive 'CCDC 1401545'
_audit_update_record             
;
2015-05-17 deposited with the CCDC.
2015-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C54 H46 N6 Ni3 O18'
_chemical_formula_weight         1243.10

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'
Ni Ni 0.3393 1.1124 '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_H-M   P21/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                   11.2710(18)
_cell_length_b                   12.618(2)
_cell_length_c                   19.339(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.01
_cell_angle_gamma                90.00
_cell_volume                     2750.3(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6959
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      28.08

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1280
_exptl_absorpt_coefficient_mu    1.095
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16747
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         26.37
_reflns_number_total             5611
_reflns_number_gt                4823
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0684P)²+6.8992P] 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         5611
_refine_ls_number_parameters     382
_refine_ls_number_restraints     29
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1402
_refine_ls_wR_factor_gt          0.1352
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.062
_refine_ls_shift/su_mean         0.002

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
Ni1 Ni 0.15367(3) -0.13804(3) 0.22498(2) 0.01960(14) Uani 1 1 d . . .
Ni2 Ni 0.5000 0.5000 0.0000 0.02153(16) Uani 1 2 d S . .
N2 N 0.1667(3) -0.0731(3) 0.12511(15) 0.0313(7) Uani 1 1 d . . .
C9 C 0.2670(4) 0.0546(3) 0.0545(2) 0.0417(10) Uani 1 1 d . . .
O4 O -0.0244(2) -0.1367(2) 0.22035(14) 0.0306(6) Uani 1 1 d . . .
O8 O 0.3349(2) -0.1335(2) 0.22351(15) 0.0345(6) Uani 1 1 d . . .
O1 O 0.3215(2) 0.5334(2) -0.00476(13) 0.0323(6) Uani 1 1 d . . .
O7 O 0.1542(2) -0.2900(2) 0.18004(14) 0.0278(5) Uani 1 1 d . . .
H7A H 0.2227 -0.3078 0.1716 0.042 Uiso 1 1 calc R . .
O3 O 0.4971(2) 0.5401(2) 0.10480(13) 0.0294(6) Uani 1 1 d . . .
H3A H 0.5653 0.5465 0.1190 0.044 Uiso 1 1 calc R . .
O6 O 0.1593(2) 0.0146(2) 0.26667(13) 0.0277(5) Uani 1 1 d . . .
H6A H 0.1826 0.0117 0.3068 0.041 Uiso 1 1 calc R . .
O2 O 0.2686(2) 0.4616(3) -0.10561(14) 0.0401(7) Uani 1 1 d . . .
N3 N 0.1510(4) -0.2906(3) -0.17774(17) 0.0404(7) Uani 1 1 d U . .
O9 O 0.3891(2) -0.2793(2) 0.16653(17) 0.0447(8) Uani 1 1 d . . .
N1 N 0.4509(3) 0.3475(3) 0.02959(17) 0.0334(7) Uani 1 1 d . . .
O5 O -0.0751(2) 0.0252(2) 0.25481(19) 0.0481(8) Uani 1 1 d . . .
C17 C 0.1183(3) 0.4995(3) -0.02254(19) 0.0304(8) Uani 1 1 d . . .
C5 C 0.4782(4) 0.2637(4) -0.0084(2) 0.0452(11) Uani 1 1 d . . .
H5 H 0.5374 0.2703 -0.0416 0.054 Uiso 1 1 calc R . .
C20 C -0.0991(3) -0.0656(3) 0.23317(19) 0.0274(7) Uani 1 1 d . . .
C6 C 0.1400(4) -0.1284(3) 0.0689(2) 0.0356(9) Uani 1 1 d . . .
H6T H 0.0944 -0.1894 0.0736 0.043 Uiso 1 1 calc R . .
C8 C 0.2403(5) -0.0048(4) -0.0034(2) 0.0491(12) Uani 1 1 d . . .
H8 H 0.2646 0.0182 -0.0469 0.059 Uiso 1 1 calc R . .
C3 C 0.3342(4) 0.1552(3) 0.0488(2) 0.0413(10) Uani 1 1 d . . .
C25 C 0.5381(3) -0.1591(3) 0.2043(2) 0.0321(8) Uani 1 1 d . . .
C7 C 0.1774(4) -0.0986(3) 0.0031(2) 0.0415(10) Uani 1 1 d . . .
C21 C -0.2261(3) -0.0962(3) 0.2219(2) 0.0303(8) Uani 1 1 d . . .
C24 C 0.4113(3) -0.1940(3) 0.1970(2) 0.0304(8) Uani 1 1 d . . .
C13 C 0.1629(5) -0.1680(3) -0.0581(2) 0.0475(8) Uani 1 1 d U . .
C10 C 0.2292(4) 0.0163(3) 0.1182(2) 0.0365(9) Uani 1 1 d . . .
H10 H 0.2483 0.0545 0.1578 0.044 Uiso 1 1 calc R . .
C27 C 0.5654(3) -0.0580(4) 0.2263(3) 0.0448(11) Uani 1 1 d . . .
H27 H 0.5045 -0.0102 0.2353 0.054 Uiso 1 1 calc R . .
C26 C 0.6304(4) -0.2287(4) 0.1907(3) 0.0599(16) Uani 1 1 d . . .
H26 H 0.6140 -0.2969 0.1751 0.072 Uiso 1 1 calc R . .
C22 C -0.3185(3) -0.0267(3) 0.2351(3) 0.0447(11) Uani 1 1 d . . .
H22 H -0.3019 0.0418 0.2500 0.054 Uiso 1 1 calc R . .
C16 C 0.2459(3) 0.4978(3) -0.04667(19) 0.0283(8) Uani 1 1 d . . .
C2 C 0.3100(5) 0.2409(4) 0.0904(2) 0.0478(12) Uani 1 1 d . . .
H2 H 0.2542 0.2353 0.1256 0.057 Uiso 1 1 calc R . .
C18 C 0.0867(3) 0.5489(4) 0.0385(2) 0.0398(10) Uani 1 1 d . . .
H18 H 0.1448 0.5819 0.0651 0.048 Uiso 1 1 calc R . .
C12 C 0.0606(6) -0.2030(5) -0.0831(3) 0.0749(15) Uani 1 1 d U . .
H12 H -0.0099 -0.1878 -0.0601 0.090 Uiso 1 1 calc R . .
C11 C 0.0586(6) -0.2623(5) -0.1434(3) 0.0684(13) Uani 1 1 d U . .
H11 H -0.0150 -0.2832 -0.1603 0.082 Uiso 1 1 calc R . .
C19 C 0.0301(3) 0.4497(4) -0.0608(2) 0.0399(10) Uani 1 1 d . . .
H19 H 0.0497 0.4152 -0.1017 0.048 Uiso 1 1 calc R . .
C23 C -0.2534(4) -0.1971(4) 0.2001(3) 0.0567(15) Uani 1 1 d . . .
H23 H -0.1924 -0.2449 0.1915 0.068 Uiso 1 1 calc R . .
C15 C 0.2516(6) -0.2661(5) -0.1489(3) 0.0723(12) Uani 1 1 d U . .
H15 H 0.3208 -0.2931 -0.1683 0.087 Uiso 1 1 calc R . .
C1 C 0.3691(4) 0.3354(4) 0.0794(2) 0.0429(10) Uani 1 1 d . . .
H1 H 0.3515 0.3929 0.1077 0.051 Uiso 1 1 calc R . .
C4 C 0.4229(5) 0.1668(4) -0.0008(2) 0.0502(12) Uani 1 1 d . . .
H4 H 0.4445 0.1098 -0.0286 0.060 Uiso 1 1 calc R . .
C14 C 0.2619(6) -0.2030(6) -0.0917(4) 0.0786(13) Uani 1 1 d U . .
H14 H 0.3366 -0.1840 -0.0756 0.094 Uiso 1 1 calc R . .
H6B H 0.086(5) 0.026(5) 0.270(3) 0.060(17) Uiso 1 1 d . . .
H3B H 0.458(4) 0.588(4) 0.123(3) 0.046(14) Uiso 1 1 d . . .
H7B H 0.125(5) -0.346(4) 0.202(3) 0.051(14) Uiso 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
Ni1 O4 2.009(2) . ?
Ni1 O8 2.044(2) . ?
Ni1 N3 2.086(3) 4_556 ?
Ni1 O6 2.089(3) . ?
Ni1 N2 2.103(3) . ?
Ni1 O7 2.105(3) . ?
Ni2 O1 2.057(2) . ?
Ni2 O1 2.057(2) 3_665 ?
Ni2 N1 2.082(3) 3_665 ?
Ni2 N1 2.082(3) . ?
Ni2 O3 2.089(3) 3_665 ?
Ni2 O3 2.089(3) . ?
N2 C6 1.326(5) . ?
N2 C10 1.337(5) . ?
C9 C8 1.382(6) . ?
C9 C10 1.390(5) . ?
C9 C3 1.482(5) . ?
O4 C20 1.255(4) . ?
O8 C24 1.259(4) . ?
O1 C16 1.259(4) . ?
O7 H7A 0.8200 . ?
O7 H7B 0.89(5) . ?
O3 H3A 0.8200 . ?
O3 H3B 0.83(5) . ?
O6 H6A 0.8200 . ?
O6 H6B 0.85(6) . ?
O2 C16 1.255(5) . ?
N3 C11 1.285(7) . ?
N3 C15 1.302(7) . ?
N3 Ni1 2.086(3) 4 ?
O9 C24 1.252(5) . ?
N1 C5 1.324(5) . ?
N1 C1 1.343(5) . ?
O5 C20 1.249(5) . ?
C17 C18 1.382(6) . ?
C17 C19 1.389(5) . ?
C17 C16 1.511(5) . ?
C5 C4 1.380(6) . ?
C5 H5 0.9300 . ?
C20 C21 1.499(5) . ?
C6 C7 1.393(6) . ?
C6 H6T 0.9300 . ?
C8 C7 1.386(6) . ?
C8 H8 0.9300 . ?
C3 C2 1.376(6) . ?
C3 C4 1.393(6) . ?
C25 C27 1.379(6) . ?
C25 C26 1.387(6) . ?
C25 C24 1.502(5) . ?
C7 C13 1.481(6) . ?
C21 C23 1.377(6) . ?
C21 C22 1.385(5) . ?
C13 C12 1.326(8) . ?
C13 C14 1.364(8) . ?
C10 H10 0.9300 . ?
C27 C22 1.378(5) 1_655 ?
C27 H27 0.9300 . ?
C26 C23 1.381(6) 1_655 ?
C26 H26 0.9300 . ?
C22 C27 1.378(5) 1_455 ?
C22 H22 0.9300 . ?
C2 C1 1.381(6) . ?
C2 H2 0.9300 . ?
C18 C19 1.386(5) 3_565 ?
C18 H18 0.9300 . ?
C12 C11 1.386(8) . ?
C12 H12 0.9300 . ?
C11 H11 0.9300 . ?
C19 C18 1.386(5) 3_565 ?
C19 H19 0.9300 . ?
C23 C26 1.381(6) 1_455 ?
C23 H23 0.9300 . ?
C15 C14 1.368(9) . ?
C15 H15 0.9300 . ?
C1 H1 0.9300 . ?
C4 H4 0.9300 . ?
C14 H14 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
O4 Ni1 O8 176.06(12) . . ?
O4 Ni1 N3 91.67(14) . 4_556 ?
O8 Ni1 N3 92.24(14) . 4_556 ?
O4 Ni1 O6 92.27(10) . . ?
O8 Ni1 O6 87.11(11) . . ?
N3 Ni1 O6 92.87(12) 4_556 . ?
O4 Ni1 N2 91.46(12) . . ?
O8 Ni1 N2 84.65(12) . . ?
N3 Ni1 N2 175.93(14) 4_556 . ?
O6 Ni1 N2 89.61(11) . . ?
O4 Ni1 O7 89.54(10) . . ?
O8 Ni1 O7 90.97(10) . . ?
N3 Ni1 O7 88.81(12) 4_556 . ?
O6 Ni1 O7 177.49(10) . . ?
N2 Ni1 O7 88.60(12) . . ?
O1 Ni2 O1 180.00(16) . 3_665 ?
O1 Ni2 N1 93.35(13) . 3_665 ?
O1 Ni2 N1 86.65(13) 3_665 3_665 ?
O1 Ni2 N1 86.65(13) . . ?
O1 Ni2 N1 93.35(13) 3_665 . ?
N1 Ni2 N1 180.00(18) 3_665 . ?
O1 Ni2 O3 91.22(10) . 3_665 ?
O1 Ni2 O3 88.78(10) 3_665 3_665 ?
N1 Ni2 O3 87.31(12) 3_665 3_665 ?
N1 Ni2 O3 92.69(12) . 3_665 ?
O1 Ni2 O3 88.78(10) . . ?
O1 Ni2 O3 91.22(10) 3_665 . ?
N1 Ni2 O3 92.69(12) 3_665 . ?
N1 Ni2 O3 87.31(12) . . ?
O3 Ni2 O3 180.0 3_665 . ?
C6 N2 C10 118.8(3) . . ?
C6 N2 Ni1 122.2(3) . . ?
C10 N2 Ni1 117.2(3) . . ?
C8 C9 C10 117.6(4) . . ?
C8 C9 C3 121.0(4) . . ?
C10 C9 C3 121.4(4) . . ?
C20 O4 Ni1 131.9(2) . . ?
C24 O8 Ni1 132.2(2) . . ?
C16 O1 Ni2 128.2(2) . . ?
Ni1 O7 H7A 109.5 . . ?
Ni1 O7 H7B 121(3) . . ?
H7A O7 H7B 103.4 . . ?
Ni2 O3 H3A 109.5 . . ?
Ni2 O3 H3B 126(3) . . ?
H3A O3 H3B 106.6 . . ?
Ni1 O6 H6A 109.5 . . ?
Ni1 O6 H6B 99(4) . . ?
H6A O6 H6B 105.1 . . ?
C11 N3 C15 114.7(5) . . ?
C11 N3 Ni1 126.7(4) . 4 ?
C15 N3 Ni1 118.5(4) . 4 ?
C5 N1 C1 117.8(3) . . ?
C5 N1 Ni2 121.6(3) . . ?
C1 N1 Ni2 119.0(3) . . ?
C18 C17 C19 118.3(3) . . ?
C18 C17 C16 121.0(3) . . ?
C19 C17 C16 120.7(3) . . ?
N1 C5 C4 123.0(4) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
O5 C20 O4 125.2(3) . . ?
O5 C20 C21 119.4(3) . . ?
O4 C20 C21 115.4(3) . . ?
N2 C6 C7 122.6(4) . . ?
N2 C6 H6T 118.7 . . ?
C7 C6 H6T 118.7 . . ?
C9 C8 C7 120.1(4) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C2 C3 C4 117.6(4) . . ?
C2 C3 C9 121.8(4) . . ?
C4 C3 C9 120.6(4) . . ?
C27 C25 C26 118.5(4) . . ?
C27 C25 C24 120.8(3) . . ?
C26 C25 C24 120.7(4) . . ?
C8 C7 C6 117.9(4) . . ?
C8 C7 C13 119.3(4) . . ?
C6 C7 C13 122.5(4) . . ?
C23 C21 C22 118.3(3) . . ?
C23 C21 C20 119.7(3) . . ?
C22 C21 C20 121.9(4) . . ?
O9 C24 O8 125.1(3) . . ?
O9 C24 C25 119.1(3) . . ?
O8 C24 C25 115.7(3) . . ?
C12 C13 C14 115.5(5) . . ?
C12 C13 C7 125.8(5) . . ?
C14 C13 C7 118.8(5) . . ?
N2 C10 C9 122.9(4) . . ?
N2 C10 H10 118.5 . . ?
C9 C10 H10 118.5 . . ?
C22 C27 C25 121.0(4) 1_655 . ?
C22 C27 H27 119.5 1_655 . ?
C25 C27 H27 119.5 . . ?
C23 C26 C25 120.2(4) 1_655 . ?
C23 C26 H26 119.9 1_655 . ?
C25 C26 H26 119.9 . . ?
C27 C22 C21 120.6(4) 1_455 . ?
C27 C22 H22 119.7 1_455 . ?
C21 C22 H22 119.7 . . ?
O2 C16 O1 125.2(3) . . ?
O2 C16 C17 118.7(3) . . ?
O1 C16 C17 116.1(3) . . ?
C3 C2 C1 119.5(4) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C17 C18 C19 121.1(4) . 3_565 ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 3_565 . ?
C13 C12 C11 120.0(6) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
N3 C11 C12 124.9(6) . . ?
N3 C11 H11 117.5 . . ?
C12 C11 H11 117.5 . . ?
C18 C19 C17 120.6(4) 3_565 . ?
C18 C19 H19 119.7 3_565 . ?
C17 C19 H19 119.7 . . ?
C21 C23 C26 121.3(4) . 1_455 ?
C21 C23 H23 119.3 . . ?
C26 C23 H23 119.3 1_455 . ?
N3 C15 C14 124.0(6) . . ?
N3 C15 H15 118.0 . . ?
C14 C15 H15 118.0 . . ?
N1 C1 C2 122.7(4) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C5 C4 C3 119.3(4) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C13 C14 C15 120.3(6) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?

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
O4 Ni1 N2 C6 -71.2(3) . . . . ?
O8 Ni1 N2 C6 109.4(3) . . . . ?
N3 Ni1 N2 C6 69(2) 4_556 . . . ?
O6 Ni1 N2 C6 -163.5(3) . . . . ?
O7 Ni1 N2 C6 18.3(3) . . . . ?
O4 Ni1 N2 C10 124.5(3) . . . . ?
O8 Ni1 N2 C10 -54.9(3) . . . . ?
N3 Ni1 N2 C10 -95.3(19) 4_556 . . . ?
O6 Ni1 N2 C10 32.3(3) . . . . ?
O7 Ni1 N2 C10 -146.0(3) . . . . ?
O8 Ni1 O4 C20 -76.0(16) . . . . ?
N3 Ni1 O4 C20 97.8(3) 4_556 . . . ?
O6 Ni1 O4 C20 4.9(3) . . . . ?
N2 Ni1 O4 C20 -84.8(3) . . . . ?
O7 Ni1 O4 C20 -173.4(3) . . . . ?
O4 Ni1 O8 C24 -89.2(16) . . . . ?
N3 Ni1 O8 C24 96.9(4) 4_556 . . . ?
O6 Ni1 O8 C24 -170.3(4) . . . . ?
N2 Ni1 O8 C24 -80.4(4) . . . . ?
O7 Ni1 O8 C24 8.1(4) . . . . ?
O1 Ni2 O1 C16 -105.1(3) 3_665 . . . ?
N1 Ni2 O1 C16 112.2(3) 3_665 . . . ?
N1 Ni2 O1 C16 -67.8(3) . . . . ?
O3 Ni2 O1 C16 24.8(3) 3_665 . . . ?
O3 Ni2 O1 C16 -155.2(3) . . . . ?
O1 Ni2 N1 C5 117.8(4) . . . . ?
O1 Ni2 N1 C5 -62.2(4) 3_665 . . . ?
N1 Ni2 N1 C5 -146(99) 3_665 . . . ?
O3 Ni2 N1 C5 26.8(4) 3_665 . . . ?
O3 Ni2 N1 C5 -153.2(4) . . . . ?
O1 Ni2 N1 C1 -47.7(3) . . . . ?
O1 Ni2 N1 C1 132.3(3) 3_665 . . . ?
N1 Ni2 N1 C1 49(99) 3_665 . . . ?
O3 Ni2 N1 C1 -138.7(3) 3_665 . . . ?
O3 Ni2 N1 C1 41.3(3) . . . . ?
C1 N1 C5 C4 3.0(7) . . . . ?
Ni2 N1 C5 C4 -162.7(4) . . . . ?
Ni1 O4 C20 O5 -2.1(6) . . . . ?
Ni1 O4 C20 C21 178.9(2) . . . . ?
C10 N2 C6 C7 1.9(7) . . . . ?
Ni1 N2 C6 C7 -162.1(4) . . . . ?
C10 C9 C8 C7 0.3(8) . . . . ?
C3 C9 C8 C7 180.0(5) . . . . ?
C8 C9 C3 C2 143.6(5) . . . . ?
C10 C9 C3 C2 -36.7(7) . . . . ?
C8 C9 C3 C4 -34.7(8) . . . . ?
C10 C9 C3 C4 145.0(5) . . . . ?
C9 C8 C7 C6 1.8(8) . . . . ?
C9 C8 C7 C13 -172.2(5) . . . . ?
N2 C6 C7 C8 -3.0(7) . . . . ?
N2 C6 C7 C13 170.8(5) . . . . ?
O5 C20 C21 C23 -178.0(5) . . . . ?
O4 C20 C21 C23 1.0(6) . . . . ?
O5 C20 C21 C22 -0.3(6) . . . . ?
O4 C20 C21 C22 178.8(4) . . . . ?
Ni1 O8 C24 O9 -4.1(7) . . . . ?
Ni1 O8 C24 C25 176.7(3) . . . . ?
C27 C25 C24 O9 168.4(4) . . . . ?
C26 C25 C24 O9 -13.1(6) . . . . ?
C27 C25 C24 O8 -12.3(6) . . . . ?
C26 C25 C24 O8 166.2(5) . . . . ?
C8 C7 C13 C12 -125.5(6) . . . . ?
C6 C7 C13 C12 60.7(7) . . . . ?
C8 C7 C13 C14 56.7(7) . . . . ?
C6 C7 C13 C14 -117.1(6) . . . . ?
C6 N2 C10 C9 0.5(7) . . . . ?
Ni1 N2 C10 C9 165.3(4) . . . . ?
C8 C9 C10 N2 -1.6(7) . . . . ?
C3 C9 C10 N2 178.7(4) . . . . ?
C26 C25 C27 C22 -0.5(8) . . . 1_655 ?
C24 C25 C27 C22 178.0(4) . . . 1_655 ?
C27 C25 C26 C23 1.0(8) . . . 1_655 ?
C24 C25 C26 C23 -177.6(5) . . . 1_655 ?
C23 C21 C22 C27 -0.2(8) . . . 1_455 ?
C20 C21 C22 C27 -178.0(4) . . . 1_455 ?
Ni2 O1 C16 O2 -23.3(6) . . . . ?
Ni2 O1 C16 C17 156.4(3) . . . . ?
C18 C17 C16 O2 -172.9(4) . . . . ?
C19 C17 C16 O2 8.1(6) . . . . ?
C18 C17 C16 O1 7.5(6) . . . . ?
C19 C17 C16 O1 -171.5(4) . . . . ?
C4 C3 C2 C1 3.2(8) . . . . ?
C9 C3 C2 C1 -175.2(5) . . . . ?
C19 C17 C18 C19 -0.8(8) . . . 3_565 ?
C16 C17 C18 C19 -179.9(4) . . . 3_565 ?
C14 C13 C12 C11 -6.1(9) . . . . ?
C7 C13 C12 C11 176.0(5) . . . . ?
C15 N3 C11 C12 5.0(9) . . . . ?
Ni1 N3 C11 C12 -171.2(5) 4 . . . ?
C13 C12 C11 N3 2.4(10) . . . . ?
C18 C17 C19 C18 0.8(8) . . . 3_565 ?
C16 C17 C19 C18 179.9(4) . . . 3_565 ?
C22 C21 C23 C26 0.7(8) . . . 1_455 ?
C20 C21 C23 C26 178.5(5) . . . 1_455 ?
C11 N3 C15 C14 -8.6(9) . . . . ?
Ni1 N3 C15 C14 168.0(5) 4 . . . ?
C5 N1 C1 C2 -2.7(7) . . . . ?
Ni2 N1 C1 C2 163.4(4) . . . . ?
C3 C2 C1 N1 -0.4(8) . . . . ?
N1 C5 C4 C3 -0.2(8) . . . . ?
C2 C3 C4 C5 -2.9(8) . . . . ?
C9 C3 C4 C5 175.5(5) . . . . ?
C12 C13 C14 C15 2.8(9) . . . . ?
C7 C13 C14 C15 -179.2(6) . . . . ?
N3 C15 C14 C13 5.0(11) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.511
_refine_diff_density_min         -1.120
_refine_diff_density_rms         0.091
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4
_database_code_depnum_ccdc_archive 'CCDC 1401546'
_audit_update_record             
;
2015-05-17 deposited with the CCDC.
2015-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 Co N4 O6'
_chemical_formula_weight         457.30

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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                   10.895(3)
_cell_length_b                   17.520(4)
_cell_length_c                   20.545(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.160(3)
_cell_angle_gamma                90.00
_cell_volume                     3871.8(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1880
_exptl_absorpt_coefficient_mu    0.933
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.7802
_exptl_absorpt_correction_T_max  0.8211
_exptl_absorpt_process_details   ?

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17854
_diffrn_reflns_av_R_equivalents  0.0737
_diffrn_reflns_av_sigmaI/netI    0.0661
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         28.21
_reflns_number_total             4746
_reflns_number_gt                3342
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0778P)²+0.0709P] 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         4746
_refine_ls_number_parameters     271
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1446
_refine_ls_wR_factor_gt          0.1298
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.425
_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
O1W O 0.447(3) 0.6593(13) 0.6814(15) 0.68(3) Uani 1 1 d D . .
H1WB H 0.3860 0.6328 0.6810 1.024 Uiso 1 1 d RD . .
H1WA H 0.5117 0.6296 0.6766 1.024 Uiso 1 1 d RD . .
O2 O 0.3558(3) 0.94386(17) 0.50388(16) 0.0364(8) Uani 1 1 d . . .
N1 N 1.4903(3) 0.9808(2) 0.86938(18) 0.0330(8) Uani 1 1 d . . .
C5 C 1.3797(5) 1.0074(3) 0.8406(2) 0.0440(13) Uani 1 1 d . . .
H5 H 1.3600 1.0579 0.8483 0.053 Uiso 1 1 calc R . .
C1 C 1.5143(4) 0.9082(3) 0.8562(2) 0.0348(10) Uani 1 1 d . . .
H1 H 1.5913 0.8885 0.8745 0.042 Uiso 1 1 calc R . .
Co1 Co 0.61894(5) 0.96007(3) 0.44289(3) 0.0252(2) Uani 1 1 d . . .
N3 N 0.7576(3) 0.9107(2) 0.51651(17) 0.0300(8) Uani 1 1 d . . .
C3 C 1.3178(4) 0.8884(3) 0.7884(2) 0.0313(10) Uani 1 1 d . . .
C18 C 0.3946(4) 0.8854(2) 0.4797(2) 0.0281(9) Uani 1 1 d . . .
C15 C 0.7492(4) 0.8412(2) 0.5429(2) 0.0308(9) Uani 1 1 d . . .
H15 H 0.6786 0.8123 0.5283 0.037 Uiso 1 1 calc R . .
C11 C 0.9468(4) 0.8520(2) 0.61270(19) 0.0260(9) Uani 1 1 d . . .
C6 C 1.2265(4) 0.8387(3) 0.74703(19) 0.0290(9) Uani 1 1 d . . .
C8 C 1.1312(4) 0.8690(3) 0.70116(19) 0.0298(9) Uani 1 1 d . . .
H8 H 1.1238 0.9217 0.6961 0.036 Uiso 1 1 calc R . .
C12 C 0.8386(4) 0.8103(3) 0.5902(2) 0.0308(9) Uani 1 1 d . . .
H12 H 0.8274 0.7620 0.6072 0.037 Uiso 1 1 calc R . .
C9 C 1.0469(4) 0.8213(2) 0.66287(19) 0.0272(9) Uani 1 1 d . . .
C13 C 0.9557(4) 0.9237(3) 0.5850(2) 0.0362(11) Uani 1 1 d . . .
H13 H 1.0255 0.9538 0.5982 0.043 Uiso 1 1 calc R . .
C2 C 1.4337(4) 0.8609(3) 0.8176(2) 0.0343(10) Uani 1 1 d . . .
H2 H 1.4560 0.8107 0.8109 0.041 Uiso 1 1 calc R . .
C14 C 0.8612(4) 0.9500(3) 0.5379(2) 0.0375(11) Uani 1 1 d . . .
H14 H 0.8699 0.9980 0.5199 0.045 Uiso 1 1 calc R . .
N2 N 1.1528(4) 0.7122(2) 0.7157(2) 0.0456(11) Uani 1 1 d . . .
C7 C 1.2320(4) 0.7593(3) 0.7522(2) 0.0397(11) Uani 1 1 d . . .
H7 H 1.2945 0.7379 0.7829 0.048 Uiso 1 1 calc R . .
C10 C 1.0631(4) 0.7431(3) 0.6727(2) 0.0377(11) Uani 1 1 d . . .
H10 H 1.0072 0.7105 0.6475 0.045 Uiso 1 1 calc R . .
O1 O 0.4963(3) 0.88056(17) 0.45847(16) 0.0359(7) Uani 1 1 d . . .
C4 C 1.2939(4) 0.9643(3) 0.8006(2) 0.0413(12) Uani 1 1 d . . .
H4 H 1.2191 0.9862 0.7814 0.050 Uiso 1 1 calc R . .
C19 C 0.3146(4) 0.8145(2) 0.4742(2) 0.0293(9) Uani 1 1 d . . .
H19 H 0.2987 0.8002 0.4275 0.035 Uiso 1 1 calc R . .
O3 O 0.7639(3) 0.9916(2) 0.38637(17) 0.0435(8) Uani 1 1 d . . .
O4 O 0.6936(4) 0.8782(2) 0.37279(19) 0.0535(10) Uani 1 1 d . . .
N4 N 0.7714(4) 0.9268(3) 0.3602(2) 0.0467(11) Uani 1 1 d . . .
C20 C 0.3862(4) 0.7484(3) 0.5115(3) 0.0391(11) Uani 1 1 d . . .
H20A H 0.4064 0.7615 0.5579 0.047 Uiso 1 1 calc R . .
H20B H 0.4635 0.7405 0.4947 0.047 Uiso 1 1 calc R . .
C21 C 0.1898(4) 0.8256(3) 0.4958(3) 0.0408(12) Uani 1 1 d . . .
H21A H 0.1442 0.8653 0.4693 0.049 Uiso 1 1 calc R . .
H21B H 0.2019 0.8419 0.5415 0.049 Uiso 1 1 calc R . .
O5 O 0.8492(4) 0.9139(3) 0.3245(2) 0.0800(14) 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
O2 C18 1.242(5) . ?
O2 Co1 2.002(3) 5_676 ?
N1 C1 1.336(6) . ?
N1 C5 1.338(6) . ?
N1 Co1 2.155(4) 6_676 ?
C5 C4 1.370(6) . ?
C1 C2 1.365(6) . ?
Co1 O1 1.991(3) . ?
Co1 O2 2.002(3) 5_676 ?
Co1 N3 2.143(3) . ?
Co1 N1 2.155(4) 6_475 ?
Co1 O3 2.175(4) . ?
Co1 O4 2.273(4) . ?
N3 C14 1.335(5) . ?
N3 C15 1.342(5) . ?
C3 C4 1.386(6) . ?
C3 C2 1.395(6) . ?
C3 C6 1.482(6) . ?
C18 O1 1.257(5) . ?
C18 C19 1.510(5) . ?
C15 C12 1.374(6) . ?
C11 C13 1.389(6) . ?
C11 C12 1.401(6) . ?
C11 C9 1.477(5) . ?
C6 C8 1.392(5) . ?
C6 C7 1.396(6) . ?
C8 C9 1.391(5) . ?
C9 C10 1.391(6) . ?
C13 C14 1.375(6) . ?
N2 C10 1.324(6) . ?
N2 C7 1.334(6) . ?
C19 C21 1.508(6) . ?
C19 C20 1.532(6) . ?
O3 N4 1.263(5) . ?
O4 N4 1.257(5) . ?
N4 O5 1.227(6) . ?
C20 C21 1.532(6) 7_566 ?
C21 C20 1.532(6) 7_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
C18 O2 Co1 152.4(3) . 5_676 ?
C1 N1 C5 115.7(4) . . ?
C1 N1 Co1 118.3(3) . 6_676 ?
C5 N1 Co1 125.6(3) . 6_676 ?
N1 C5 C4 123.7(5) . . ?
N1 C1 C2 124.6(4) . . ?
O1 Co1 O2 122.53(14) . 5_676 ?
O1 Co1 N3 91.14(13) . . ?
O2 Co1 N3 86.19(13) 5_676 . ?
O1 Co1 N1 94.06(13) . 6_475 ?
O2 Co1 N1 89.80(14) 5_676 6_475 ?
N3 Co1 N1 174.61(14) . 6_475 ?
O1 Co1 O3 145.70(14) . . ?
O2 Co1 O3 91.73(13) 5_676 . ?
N3 Co1 O3 89.37(14) . . ?
N1 Co1 O3 87.16(14) 6_475 . ?
O1 Co1 O4 88.70(13) . . ?
O2 Co1 O4 147.63(13) 5_676 . ?
N3 Co1 O4 84.80(14) . . ?
N1 Co1 O4 96.75(15) 6_475 . ?
O3 Co1 O4 57.19(13) . . ?
C14 N3 C15 116.3(4) . . ?
C14 N3 Co1 119.2(3) . . ?
C15 N3 Co1 124.5(3) . . ?
C4 C3 C2 115.8(4) . . ?
C4 C3 C6 122.6(4) . . ?
C2 C3 C6 121.5(4) . . ?
O2 C18 O1 124.7(4) . . ?
O2 C18 C19 118.6(4) . . ?
O1 C18 C19 116.7(4) . . ?
N3 C15 C12 123.9(4) . . ?
C13 C11 C12 116.5(4) . . ?
C13 C11 C9 121.6(4) . . ?
C12 C11 C9 121.9(4) . . ?
C8 C6 C7 116.7(4) . . ?
C8 C6 C3 121.6(4) . . ?
C7 C6 C3 121.7(4) . . ?
C9 C8 C6 120.5(4) . . ?
C15 C12 C11 119.5(4) . . ?
C8 C9 C10 116.9(4) . . ?
C8 C9 C11 121.5(4) . . ?
C10 C9 C11 121.5(4) . . ?
C14 C13 C11 119.9(4) . . ?
C1 C2 C3 119.7(4) . . ?
N3 C14 C13 123.9(4) . . ?
C10 N2 C7 117.7(4) . . ?
N2 C7 C6 123.9(4) . . ?
N2 C10 C9 124.2(4) . . ?
C18 O1 Co1 131.3(3) . . ?
C5 C4 C3 120.5(4) . . ?
C21 C19 C18 114.2(4) . . ?
C21 C19 C20 111.1(4) . . ?
C18 C19 C20 110.0(3) . . ?
N4 O3 Co1 95.8(3) . . ?
N4 O4 Co1 91.4(3) . . ?
O5 N4 O4 123.4(5) . . ?
O5 N4 O3 121.2(5) . . ?
O4 N4 O3 115.4(4) . . ?
C19 C20 C21 111.5(4) . 7_566 ?
C19 C21 C20 111.1(4) . 7_566 ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        28.21
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.085
