# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# 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_13sb002
_database_code_depnum_ccdc_archive 'CCDC 1407120'
_audit_update_record             
;
2015-06-16 deposited with the CCDC.
2015-08-24 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 H20 Co N4 O6'
_chemical_formula_weight         459.32

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                   19.2106(11)
_cell_length_b                   13.5093(7)
_cell_length_c                   18.6918(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.602(2)
_cell_angle_gamma                90.00
_cell_volume                     4337.4(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2292
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      28.19

_exptl_crystal_description       Prism
_exptl_crystal_colour            Purple
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1896
_exptl_absorpt_coefficient_mu    0.833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8431
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'SADABS v.2.03 (Bruker, 2001),R(int)=0.1719 before correction'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(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 APEX-2 CCD area detector'
_diffrn_measurement_method       '/w scans'
_diffrn_detector_area_resol_mean 8
_diffrn_standards_decay_%        0
_diffrn_reflns_number            24928
_diffrn_reflns_av_R_equivalents  0.1023
_diffrn_reflns_av_sigmaI/netI    0.0789
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4681
_reflns_number_gt                2824
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX-2'
_computing_cell_refinement       'Bruker APEX-2'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4681
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1774
_refine_ls_R_factor_gt           0.1249
_refine_ls_wR_factor_ref         0.3408
_refine_ls_wR_factor_gt          0.3020
_refine_ls_goodness_of_fit_ref   1.921
_refine_ls_restrained_S_all      1.921
_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 -0.55369(5) -0.26015(6) -0.05365(5) 0.0348(4) Uani 1 1 d . . .
N3 N -0.6078(3) -0.3593(4) -0.1400(3) 0.0449(14) Uani 1 1 d . . .
N4 N -0.6184(3) -0.4535(4) -0.1217(3) 0.0372(13) Uani 1 1 d . . .
H4A H -0.6025 -0.4755 -0.0738 0.045 Uiso 1 1 calc R A .
C12 C -0.5496(4) -0.3771(6) 0.0800(4) 0.0462(18) Uani 1 1 d . . .
O2 O -0.5627(3) -0.4586(4) 0.0428(3) 0.0643(16) Uani 1 1 d . . .
C13 C -0.5237(4) -0.3776(5) 0.1675(4) 0.0399(15) Uani 1 1 d . . .
C14 C -0.5127(4) -0.4640(5) 0.2103(4) 0.0461(17) Uani 1 1 d . . .
O1 O -0.5562(3) -0.2923(4) 0.0468(3) 0.0554(14) Uani 1 1 d . . .
C4 C -0.6405(4) -0.3535(5) -0.2207(4) 0.0429(16) Uani 1 1 d . . .
C5 C -0.6699(4) -0.4457(5) -0.2541(4) 0.0409(16) Uani 1 1 d . A .
C6 C -0.6564(4) -0.5072(5) -0.1870(4) 0.0478(18) Uani 1 1 d . A .
C10 C -0.6345(5) -0.2614(5) -0.2628(4) 0.050(2) Uani 1 1 d . . .
H10A H -0.6336 -0.2043 -0.2317 0.075 Uiso 1 1 calc R . .
H10B H -0.6787 -0.2574 -0.3145 0.075 Uiso 1 1 calc R . .
H10C H -0.5876 -0.2635 -0.2690 0.075 Uiso 1 1 calc R . .
C7 C -0.7107(4) -0.4742(6) -0.3401(4) 0.0495(19) Uani 1 1 d . . .
H7A H -0.7177 -0.4149 -0.3718 0.059 Uiso 1 1 calc R A .
H7B H -0.6766 -0.5179 -0.3511 0.059 Uiso 1 1 calc R . .
C11 C -0.6740(5) -0.6149(5) -0.1834(4) 0.058(2) Uani 1 1 d . . .
H11A H -0.6484 -0.6372 -0.1289 0.087 Uiso 1 1 calc R A .
H11B H -0.6557 -0.6525 -0.2151 0.087 Uiso 1 1 calc R . .
H11C H -0.7292 -0.6237 -0.2039 0.087 Uiso 1 1 calc R . .
C15 C -0.5115(5) -0.2903(6) 0.2086(4) 0.054(2) Uani 1 1 d . . .
O3' O -0.5444(7) -0.1973(7) 0.1703(6) 0.058(3) Uani 0.50 1 d P . .
H3'A H -0.5562 -0.2010 0.1225 0.087 Uiso 0.50 1 calc PR . .
O3 O -0.5320(6) -0.5607(7) 0.1762(5) 0.060(3) Uani 0.50 1 d P . .
H3A H -0.5458 -0.5574 0.1279 0.090 Uiso 0.50 1 calc PR . .
C17 C -0.3286(7) -0.2311(8) -0.0203(7) 0.076(3) Uiso 1 1 d . . .
C19 C -0.2941(8) -0.3323(10) 0.0058(7) 0.032(3) Uiso 0.50 1 d P . .
C18 C -0.2852(7) -0.1555(8) -0.0246(6) 0.085(3) Uiso 1 1 d . . .
C16 C -0.4092(9) -0.1915(11) -0.0439(8) 0.040(3) Uiso 0.50 1 d P A .
O4 O -0.4482(7) -0.2560(8) -0.0311(7) 0.045(2) Uiso 0.50 1 d P A .
O5 O -0.4371(6) -0.1108(7) -0.0700(6) 0.051(2) Uiso 0.50 1 d P . .
O6 O -0.2973(6) -0.0621(7) -0.0553(6) 0.048(2) Uiso 0.50 1 d P . .
C16' C -0.4106(16) -0.2682(16) -0.0317(14) 0.078(6) Uiso 0.50 1 d P A 2
O4' O -0.4372(8) -0.3479(11) -0.0186(9) 0.089(4) Uiso 0.50 1 d P A 2
O5' O -0.4515(8) -0.1952(11) -0.0499(7) 0.067(3) Uiso 0.50 1 d P A 2
C19' C -0.3180(12) -0.2927(18) -0.0012(12) 0.069(5) Uiso 0.50 1 d P . 2
O6' O -0.3101(10) -0.4339(12) 0.0054(10) 0.112(5) Uiso 0.50 1 d P B 3
N1 N -0.8840(3) -0.6354(4) -0.4154(3) 0.0422(14) Uani 1 1 d . . .
N2 N -0.9107(3) -0.5518(4) -0.3922(3) 0.0455(15) Uani 1 1 d . A .
H2A H -0.9561 -0.5455 -0.3944 0.055 Uiso 1 1 calc R . .
C3 C -0.8536(4) -0.4807(5) -0.3652(4) 0.0469(18) Uani 1 1 d . . .
C1 C -0.8092(3) -0.6174(5) -0.3992(4) 0.0387(16) Uani 1 1 d . . .
C2 C -0.7856(4) -0.5224(5) -0.3679(4) 0.0443(17) Uani 1 1 d . A .
C8 C -0.7637(5) -0.6975(9) -0.4111(6) 0.085(3) Uani 1 1 d . A .
H8A H -0.7982 -0.7428 -0.4507 0.127 Uiso 1 1 calc R . .
H8B H -0.7351 -0.7320 -0.3616 0.127 Uiso 1 1 calc R . .
H8C H -0.7280 -0.6700 -0.4289 0.127 Uiso 1 1 calc R . .
C9 C -0.8685(7) -0.3828(6) -0.3371(6) 0.082(3) Uani 1 1 d . A .
H9A H -0.9163 -0.3859 -0.3327 0.123 Uiso 1 1 calc R . .
H9B H -0.8723 -0.3324 -0.3749 0.123 Uiso 1 1 calc R . .
H9C H -0.8264 -0.3675 -0.2858 0.123 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 O4 1.877(12) . ?
Co1 O1 1.950(5) . ?
Co1 N3 1.994(5) . ?
Co1 N1 1.997(6) 4_354 ?
Co1 O5' 2.122(14) . ?
Co1 O4' 2.351(15) . ?
N3 C4 1.352(8) . ?
N3 N4 1.356(8) . ?
N4 C6 1.324(8) . ?
N4 H4A 0.8600 . ?
C12 O2 1.267(9) . ?
C12 O1 1.282(9) . ?
C12 C13 1.481(9) . ?
C13 C15 1.370(10) . ?
C13 C14 1.377(9) . ?
C14 C14 1.338(13) 2_455 ?
C14 O3 1.428(10) . ?
C4 C5 1.394(9) . ?
C4 C10 1.504(9) . ?
C5 C6 1.428(9) . ?
C5 C7 1.489(8) . ?
C6 C11 1.501(10) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C7 C2 1.448(9) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C15 C15 1.406(13) 2_455 ?
C15 O3' 1.444(12) . ?
O3' H3'A 0.8200 . ?
O3 H3A 0.8200 . ?
C17 C19' 0.89(2) . ?
C17 C18 1.342(14) . ?
C17 C19 1.502(16) . ?
C17 C16 1.506(19) . ?
C17 C16' 1.57(3) . ?
C19 C19' 0.68(2) . ?
C19 O6' 1.406(19) . ?
C19 C18 1.412(18) 7_445 ?
C18 O6 1.362(13) . ?
C18 C19 1.412(18) 7_445 ?
C18 C19' 1.95(2) 7_445 ?
C16 O5' 0.771(16) . ?
C16 C16' 1.06(2) . ?
C16 O5 1.216(17) . ?
C16 O4 1.240(19) . ?
O4 C16' 0.75(2) . ?
O4 O5' 0.884(14) . ?
O4 O4' 1.263(17) . ?
O5 O5' 1.270(16) . ?
C16' O5' 1.21(3) . ?
C16' O4' 1.26(3) . ?
C16' C19' 1.64(3) . ?
C19' C18 1.95(2) 7_445 ?
N1 C1 1.351(8) . ?
N1 N2 1.389(7) . ?
N1 Co1 1.997(6) 4_344 ?
N2 C3 1.371(9) . ?
N2 H2A 0.8600 . ?
C3 C2 1.443(10) . ?
C3 C9 1.497(10) . ?
C1 C2 1.399(9) . ?
C1 C8 1.469(11) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

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 O1 106.3(4) . . ?
O4 Co1 N3 108.7(4) . . ?
O1 Co1 N3 113.6(2) . . ?
O4 Co1 N1 119.2(4) . 4_354 ?
O1 Co1 N1 101.3(2) . 4_354 ?
N3 Co1 N1 107.7(2) . 4_354 ?
O4 Co1 O5' 24.6(4) . . ?
O1 Co1 O5' 118.8(4) . . ?
N3 Co1 O5' 116.3(4) . . ?
N1 Co1 O5' 95.0(4) 4_354 . ?
O4 Co1 O4' 32.3(5) . . ?
O1 Co1 O4' 92.9(4) . . ?
N3 Co1 O4' 88.5(4) . . ?
N1 Co1 O4' 151.5(4) 4_354 . ?
O5' Co1 O4' 56.5(5) . . ?
C4 N3 N4 106.8(5) . . ?
C4 N3 Co1 132.6(5) . . ?
N4 N3 Co1 120.6(4) . . ?
C6 N4 N3 111.4(5) . . ?
C6 N4 H4A 124.3 . . ?
N3 N4 H4A 124.3 . . ?
O2 C12 O1 123.9(6) . . ?
O2 C12 C13 119.3(7) . . ?
O1 C12 C13 116.8(6) . . ?
C15 C13 C14 117.5(6) . . ?
C15 C13 C12 120.2(6) . . ?
C14 C13 C12 122.3(6) . . ?
C14 C14 C13 121.9(4) 2_455 . ?
C14 C14 O3 112.9(5) 2_455 . ?
C13 C14 O3 125.1(7) . . ?
C12 O1 Co1 128.7(5) . . ?
N3 C4 C5 109.9(6) . . ?
N3 C4 C10 121.7(6) . . ?
C5 C4 C10 128.0(6) . . ?
C4 C5 C6 104.4(5) . . ?
C4 C5 C7 128.8(6) . . ?
C6 C5 C7 126.7(6) . . ?
N4 C6 C5 107.4(6) . . ?
N4 C6 C11 122.1(6) . . ?
C5 C6 C11 130.4(6) . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2 C7 C5 117.4(6) . . ?
C2 C7 H7A 107.9 . . ?
C5 C7 H7A 107.9 . . ?
C2 C7 H7B 107.9 . . ?
C5 C7 H7B 107.9 . . ?
H7A C7 H7B 107.2 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C15 C15 120.5(4) . 2_455 ?
C13 C15 O3' 123.0(7) . . ?
C15 C15 O3' 113.5(5) 2_455 . ?
C15 O3' H3'A 109.5 . . ?
C14 O3 H3A 109.5 . . ?
C19' C17 C18 134.2(18) . . ?
C19' C17 C19 14.8(15) . . ?
C18 C17 C19 121.1(11) . . ?
C19' C17 C16 117.9(18) . . ?
C18 C17 C16 107.3(10) . . ?
C19 C17 C16 131.6(11) . . ?
C19' C17 C16' 78.0(17) . . ?
C18 C17 C16' 147.6(13) . . ?
C19 C17 C16' 91.3(11) . . ?
C16 C17 C16' 40.3(10) . . ?
C19' C19 O6' 130(3) . . ?
C19' C19 C18 135(3) . 7_445 ?
O6' C19 C18 95.5(12) . 7_445 ?
C19' C19 C17 20(2) . . ?
O6' C19 C17 145.4(13) . . ?
C18 C19 C17 117.2(10) 7_445 . ?
C17 C18 O6 137.4(12) . . ?
C17 C18 C19 121.7(10) . 7_445 ?
O6 C18 C19 100.0(10) . 7_445 ?
C17 C18 C19' 107.6(10) . 7_445 ?
O6 C18 C19' 113.5(11) . 7_445 ?
C19 C18 C19' 14.3(8) 7_445 7_445 ?
O5' C16 C16' 81(2) . . ?
O5' C16 O5 75.8(18) . . ?
C16' C16 O5 156(2) . . ?
O5' C16 O4 45.1(14) . . ?
C16' C16 O4 36.8(14) . . ?
O5 C16 O4 120.8(15) . . ?
O5' C16 C17 154(2) . . ?
C16' C16 C17 73.3(18) . . ?
O5 C16 C17 130.2(14) . . ?
O4 C16 C17 109.0(13) . . ?
C16' O4 O5' 96(2) . . ?
C16' O4 C16 59(2) . . ?
O5' O4 C16 38.1(11) . . ?
C16' O4 O4' 73(2) . . ?
O5' O4 O4' 164.3(18) . . ?
C16 O4 O4' 131.4(15) . . ?
C16' O4 Co1 161(2) . . ?
O5' O4 Co1 93.4(14) . . ?
C16 O4 Co1 131.5(11) . . ?
O4' O4 Co1 95.0(10) . . ?
C16 O5 O5' 36.0(8) . . ?
O4 C16' C16 85(2) . . ?
O4 C16' O5' 46.7(16) . . ?
C16 C16' O5' 38.9(11) . . ?
O4 C16' O4' 73(2) . . ?
C16 C16' O4' 157(3) . . ?
O5' C16' O4' 119(3) . . ?
O4 C16' C17 148(3) . . ?
C16 C16' C17 66.4(17) . . ?
O5' C16' C17 105.3(19) . . ?
O4' C16' C17 135(2) . . ?
O4 C16' C19' 161(3) . . ?
C16 C16' C19' 98(2) . . ?
O5' C16' C19' 137(2) . . ?
O4' C16' C19' 103.3(19) . . ?
C17 C16' C19' 32.2(10) . . ?
C16' O4' O4 34.3(11) . . ?
C16' O4' Co1 86.2(14) . . ?
O4 O4' Co1 52.7(8) . . ?
C16 O5' O4 97(2) . . ?
C16 O5' C16' 60.1(19) . . ?
O4 O5' C16' 37.8(14) . . ?
C16 O5' O5 68.2(17) . . ?
O4 O5' O5 164.8(18) . . ?
C16' O5' O5 128(2) . . ?
C16 O5' Co1 159(2) . . ?
O4 O5' Co1 62.0(12) . . ?
C16' O5' Co1 98.5(17) . . ?
O5 O5' Co1 133.1(10) . . ?
C19 C19' C17 146(3) . . ?
C19 C19' C16' 140(3) . . ?
C17 C19' C16' 69.9(18) . . ?
C19 C19' C18 31.0(19) . 7_445 ?
C17 C19' C18 117.2(18) . 7_445 ?
C16' C19' C18 169.6(16) . 7_445 ?
C1 N1 N2 106.8(5) . . ?
C1 N1 Co1 131.0(4) . 4_344 ?
N2 N1 Co1 121.3(4) . 4_344 ?
C3 N2 N1 109.7(6) . . ?
C3 N2 H2A 125.1 . . ?
N1 N2 H2A 125.1 . . ?
N2 C3 C2 107.5(6) . . ?
N2 C3 C9 120.0(7) . . ?
C2 C3 C9 132.4(7) . . ?
N1 C1 C2 111.8(6) . . ?
N1 C1 C8 118.6(6) . . ?
C2 C1 C8 129.5(7) . . ?
C1 C2 C3 104.1(6) . . ?
C1 C2 C7 130.2(7) . . ?
C3 C2 C7 125.6(7) . . ?
C1 C8 H8A 109.5 . . ?
C1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C3 C9 H9A 109.5 . . ?
C3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.940
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.940
_refine_diff_density_max         1.269
_refine_diff_density_min         -1.339
_refine_diff_density_rms         0.218
####################################################################### 
# 
# 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_12sb007_0m_sq_d
_database_code_depnum_ccdc_archive 'CCDC 1407121'
_audit_update_record             
;
2015-06-16 deposited with the CCDC.
2015-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C68 H64 Co2 N8 O14'
_chemical_formula_weight         1335.13

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                   38.226(7)
_cell_length_b                   13.456(2)
_cell_length_c                   33.945(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.132(11)
_cell_angle_gamma                90.00
_cell_volume                     16394(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    14708
_cell_measurement_theta_min      2.202
_cell_measurement_theta_max      24.84

_exptl_crystal_description       Block
_exptl_crystal_colour            Purple
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.082
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             5552
_exptl_absorpt_coefficient_mu    0.461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8888
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
'SADABS v.2.03 (Bruker, 2001),wR2(int)= 0.0923 before correction'


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(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 APEX-2 CCD area detector'
_diffrn_measurement_method       '/w scans'
_diffrn_detector_area_resol_mean 8
_diffrn_reflns_number            93123
_diffrn_reflns_av_R_equivalents  0.2029
_diffrn_reflns_av_sigmaI/netI    0.1938
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         1.13
_diffrn_reflns_theta_max         24.84
_reflns_number_total             14029
_reflns_number_gt                5685
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX-2'
_computing_cell_refinement       'Bruker APEX-2'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0877P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         14029
_refine_ls_number_parameters     824
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1830
_refine_ls_R_factor_gt           0.0803
_refine_ls_wR_factor_ref         0.2274
_refine_ls_wR_factor_gt          0.1887
_refine_ls_goodness_of_fit_ref   0.893
_refine_ls_restrained_S_all      0.893
_refine_ls_shift/su_max          0.002
_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 0.00961(2) 0.31545(6) 0.04214(3) 0.0548(3) Uani 1 1 d . . .
Co2 Co 0.28975(2) 0.38202(6) 0.46733(3) 0.0514(3) Uani 1 1 d . . .
O5B O 0.26213(12) 0.3689(3) 0.40031(12) 0.0634(12) Uani 1 1 d . . .
O6C O 0.21829(11) 0.3357(3) -0.01576(14) 0.0635(12) Uani 1 1 d . . .
O3C O 0.11850(11) 0.2859(3) 0.04194(14) 0.0655(12) Uani 1 1 d . . .
H3CA H 0.0982 0.2988 0.0440 0.098 Uiso 1 1 calc R . .
O6B O 0.22392(13) 0.3805(4) 0.32096(13) 0.0905(16) Uani 1 1 d . . .
H6BA H 0.2405 0.3934 0.3432 0.136 Uiso 1 1 calc R . .
O1B O 0.02423(13) 0.3761(4) 0.09889(14) 0.0763(14) Uani 1 1 d . . .
O1C O 0.04867(10) 0.3215(3) 0.01738(14) 0.0605(12) Uani 1 1 d . . .
N2A N -0.04400(14) 0.4194(4) -0.03132(18) 0.0616(15) Uani 1 1 d . . .
H2AA H -0.0291 0.4132 -0.0452 0.074 Uiso 1 1 calc R . .
O2C O 0.01632(12) 0.3453(4) -0.05005(15) 0.0791(14) Uani 1 1 d . . .
O2B O 0.06344(13) 0.2583(4) 0.10729(14) 0.0871(16) Uani 1 1 d . . .
O4B O 0.23739(10) 0.2982(3) 0.44170(13) 0.0599(11) Uani 1 1 d . . .
C21B C 0.20679(17) 0.2742(5) 0.36923(18) 0.0532(16) Uani 1 1 d . . .
N1A N -0.03429(13) 0.3983(4) 0.00986(17) 0.0550(14) Uani 1 1 d . . .
O3B O 0.12198(12) 0.2473(4) 0.17259(13) 0.0781(14) Uani 1 1 d . . .
H3BA H 0.1073 0.2328 0.1493 0.117 Uiso 1 1 calc R . .
C1A C -0.06472(17) 0.4190(5) 0.0196(2) 0.0573(17) Uani 1 1 d . . .
C12C C 0.18163(16) 0.2321(5) 0.0282(2) 0.0600(18) Uani 1 1 d . . .
H12A H 0.1974 0.1889 0.0187 0.072 Uiso 1 1 calc R . .
H12B H 0.1762 0.1979 0.0506 0.072 Uiso 1 1 calc R . .
C22C C 0.22082(17) 0.3739(5) 0.0217(2) 0.0534(16) Uani 1 1 d . . .
C23B C 0.23677(17) 0.3173(5) 0.40486(19) 0.0487(16) Uani 1 1 d . . .
C12B C 0.16667(19) 0.3165(6) 0.2504(2) 0.078(2) Uani 1 1 d . . .
H12C H 0.1707 0.2640 0.2329 0.094 Uiso 1 1 calc R . .
H12D H 0.1857 0.3665 0.2533 0.094 Uiso 1 1 calc R . .
N7A N -0.01030(14) 0.1768(4) 0.04049(18) 0.0621(15) Uani 1 1 d . . .
C11C C 0.14530(16) 0.2475(4) -0.0079(2) 0.0497(16) Uani 1 1 d . . .
C1C C 0.04568(18) 0.3240(5) -0.0214(2) 0.0564(17) Uani 1 1 d . . .
C2C C 0.07974(16) 0.2963(4) -0.0310(2) 0.0514(16) Uani 1 1 d . . .
C3C C 0.11463(17) 0.2767(4) 0.0012(2) 0.0488(16) Uani 1 1 d . . .
C1B C 0.0519(2) 0.3294(5) 0.1215(2) 0.0548(17) Uani 1 1 d . . .
C18A C -0.06708(17) -0.0473(5) -0.0005(2) 0.070(2) Uani 1 1 d . . .
H18A H -0.0570 -0.0723 -0.0212 0.084 Uiso 1 1 calc R . .
H18B H -0.0668 -0.1017 0.0184 0.084 Uiso 1 1 calc R . .
C16A C -0.04172(17) 0.0337(5) 0.0243(2) 0.0584(17) Uani 1 1 d . . .
C22B C 0.20161(19) 0.3086(5) 0.3273(2) 0.0660(19) Uani 1 1 d . . .
C10C C 0.14134(19) 0.2272(5) -0.0501(2) 0.0629(18) Uani 1 1 d . . .
C13C C 0.20357(16) 0.3268(5) 0.0463(2) 0.0536(17) Uani 1 1 d . . .
C19C C 0.22706(18) 0.4570(6) 0.0990(2) 0.0647(19) Uani 1 1 d . . .
N8A N -0.00339(15) 0.1184(5) 0.0743(2) 0.0789(18) Uani 1 1 d . . .
H8AA H 0.0115 0.1345 0.0989 0.095 Uiso 1 1 calc R . .
C14B C 0.1501(2) 0.1946(6) 0.2993(2) 0.076(2) Uani 1 1 d . . .
C15A C -0.03333(17) 0.1237(5) 0.0095(2) 0.0603(18) Uani 1 1 d . . .
C14C C 0.20718(16) 0.3679(6) 0.0862(2) 0.0598(18) Uani 1 1 d . . .
C20C C 0.24482(16) 0.5018(5) 0.0737(2) 0.0592(18) Uani 1 1 d . . .
H20A H 0.2585 0.5596 0.0828 0.071 Uiso 1 1 calc R . .
C2B C 0.07356(18) 0.3670(5) 0.16410(19) 0.0590(18) Uani 1 1 d . . .
C5B C 0.1292(2) 0.3630(6) 0.2274(2) 0.072(2) Uani 1 1 d . . .
C13B C 0.17271(19) 0.2733(6) 0.29326(19) 0.0663(19) Uani 1 1 d . . .
C5C C 0.1068(2) 0.2492(5) -0.0838(2) 0.0655(19) Uani 1 1 d . . .
C3A C -0.07860(19) 0.4504(4) -0.0480(2) 0.0612(18) Uani 1 1 d . . .
C15C C 0.19001(18) 0.3242(6) 0.1131(2) 0.079(2) Uani 1 1 d . . .
H15A H 0.1763 0.2660 0.1050 0.095 Uiso 1 1 calc R . .
C9C C 0.1701(2) 0.1826(5) -0.0627(3) 0.075(2) Uani 1 1 d . . .
H9CA H 0.1928 0.1660 -0.0423 0.090 Uiso 1 1 calc R . .
C4B C 0.10813(19) 0.3264(6) 0.1883(2) 0.0641(18) Uani 1 1 d . . .
C13A C -0.10658(16) -0.0168(4) -0.0226(2) 0.0512(16) Uani 1 1 d . . .
C21C C 0.24231(16) 0.4619(5) 0.0359(2) 0.0536(17) Uani 1 1 d . . .
C9A C -0.0962(2) 0.4768(6) -0.0932(2) 0.089(2) Uani 1 1 d . . .
H9AA H -0.0786 0.4667 -0.1073 0.134 Uiso 1 1 calc R . .
H9AB H -0.1038 0.5452 -0.0956 0.134 Uiso 1 1 calc R . .
H9AC H -0.1176 0.4354 -0.1058 0.134 Uiso 1 1 calc R . .
C6C C 0.1014(2) 0.2303(6) -0.1262(2) 0.087(2) Uani 1 1 d . . .
H6CA H 0.0789 0.2445 -0.1474 0.105 Uiso 1 1 calc R . .
C4C C 0.07717(18) 0.2852(5) -0.0719(2) 0.0611(18) Uani 1 1 d . . .
H4CA H 0.0549 0.3022 -0.0928 0.073 Uiso 1 1 calc R . .
C19B C 0.1557(2) 0.1588(6) 0.3398(2) 0.077(2) Uani 1 1 d . . .
C18B C 0.1332(3) 0.0842(7) 0.3474(3) 0.125(4) Uani 1 1 d . . .
H18C H 0.1373 0.0616 0.3745 0.150 Uiso 1 1 calc R . .
C2A C -0.09324(16) 0.4528(4) -0.0156(2) 0.0564(17) Uani 1 1 d . . .
C21A C -0.0476(2) 0.1607(6) -0.0357(2) 0.095(3) Uani 1 1 d . . .
H21A H -0.0372 0.2250 -0.0371 0.142 Uiso 1 1 calc R . .
H21B H -0.0743 0.1654 -0.0452 0.142 Uiso 1 1 calc R . .
H21C H -0.0403 0.1151 -0.0532 0.142 Uiso 1 1 calc R . .
C18C C 0.2311(2) 0.4984(8) 0.1383(3) 0.106(3) Uani 1 1 d . . .
H18D H 0.2450 0.5561 0.1471 0.128 Uiso 1 1 calc R . .
C17A C -0.0219(2) 0.0333(6) 0.0660(2) 0.077(2) Uani 1 1 d . . .
C7C C 0.1311(3) 0.1896(7) -0.1351(3) 0.103(3) Uani 1 1 d . . .
H7CA H 0.1287 0.1786 -0.1630 0.124 Uiso 1 1 calc R . .
C15B C 0.1212(3) 0.1520(6) 0.2660(2) 0.104(3) Uani 1 1 d . . .
H15B H 0.1169 0.1735 0.2387 0.124 Uiso 1 1 calc R . .
C16C C 0.1937(2) 0.3679(8) 0.1510(3) 0.101(3) Uani 1 1 d . . .
H16A H 0.1819 0.3392 0.1680 0.122 Uiso 1 1 calc R . .
C20B C 0.1832(2) 0.2017(5) 0.3739(2) 0.073(2) Uani 1 1 d . . .
H20B H 0.1857 0.1806 0.4008 0.087 Uiso 1 1 calc R . .
C8C C 0.1647(2) 0.1644(6) -0.1035(3) 0.090(2) Uani 1 1 d . . .
H8CA H 0.1835 0.1347 -0.1108 0.108 Uiso 1 1 calc R . .
C16B C 0.0993(3) 0.0796(8) 0.2732(3) 0.168(6) Uani 1 1 d . . .
H16B H 0.0802 0.0527 0.2507 0.202 Uiso 1 1 calc R . .
C8A C -0.06520(18) 0.4070(6) 0.0631(2) 0.087(2) Uani 1 1 d . . .
H8AB H -0.0415 0.3824 0.0810 0.130 Uiso 1 1 calc R . .
H8AC H -0.0844 0.3607 0.0629 0.130 Uiso 1 1 calc R . .
H8AD H -0.0701 0.4700 0.0734 0.130 Uiso 1 1 calc R . .
C11B C 0.0794(3) 0.4811(7) 0.2216(3) 0.104(3) Uani 1 1 d . . .
C3B C 0.0595(2) 0.4426(6) 0.1805(2) 0.086(2) Uani 1 1 d . . .
H3BB H 0.0366 0.4701 0.1648 0.103 Uiso 1 1 calc R . .
C17C C 0.2142(3) 0.4528(9) 0.1641(3) 0.127(4) Uani 1 1 d . . .
H17A H 0.2169 0.4799 0.1902 0.152 Uiso 1 1 calc R . .
C6B C 0.1151(3) 0.4434(6) 0.2437(2) 0.087(2) Uani 1 1 d . . .
C10B C 0.0647(3) 0.5605(9) 0.2386(3) 0.176(6) Uani 1 1 d . . .
H10A H 0.0411 0.5850 0.2239 0.211 Uiso 1 1 calc R . .
C22A C -0.0190(3) -0.0396(7) 0.1008(3) 0.136(4) Uani 1 1 d . . .
H22A H -0.0019 -0.0145 0.1268 0.204 Uiso 1 1 calc R . .
H22B H -0.0101 -0.1023 0.0945 0.204 Uiso 1 1 calc R . .
H22C H -0.0431 -0.0485 0.1032 0.204 Uiso 1 1 calc R . .
C17B C 0.1046(3) 0.0446(9) 0.3135(4) 0.160(5) Uani 1 1 d . . .
H17B H 0.0893 -0.0047 0.3177 0.192 Uiso 1 1 calc R . .
C7B C 0.1345(3) 0.4876(7) 0.2831(3) 0.121(3) Uani 1 1 d . . .
H7BA H 0.1580 0.4645 0.2991 0.145 Uiso 1 1 calc R . .
C8B C 0.1188(4) 0.5637(9) 0.2976(3) 0.178(6) Uani 1 1 d . . .
H8BA H 0.1319 0.5913 0.3237 0.213 Uiso 1 1 calc R . .
C9B C 0.0847(4) 0.6004(10) 0.2755(4) 0.203(7) Uani 1 1 d . . .
H9BA H 0.0752 0.6537 0.2860 0.244 Uiso 1 1 calc R . .
O1W O 0.28336(16) 0.5469(5) 0.35078(17) 0.124(2) Uani 1 1 d . . .
O2W O 0.2590(3) 0.1457(8) 0.1597(3) 0.227(4) Uiso 1 1 d . . .
C12A C -0.13091(18) 0.0250(4) -0.0045(2) 0.0504(16) Uani 1 1 d . . .
C14A C -0.12669(19) -0.0273(5) -0.0639(2) 0.0586(17) Uani 1 1 d . . .
N6A N -0.16151(14) 0.0075(4) -0.07028(16) 0.0604(15) Uani 1 1 d . . .
H6AA H -0.1791 0.0088 -0.0943 0.073 Uiso 1 1 calc R . .
N5A N -0.16500(12) 0.0401(4) -0.03393(16) 0.0496(13) Uani 1 1 d . . .
C19A C -0.12474(18) 0.0547(5) 0.0386(2) 0.074(2) Uani 1 1 d . . .
H19A H -0.1474 0.0811 0.0406 0.110 Uiso 1 1 calc R . .
H19B H -0.1057 0.1046 0.0470 0.110 Uiso 1 1 calc R . .
H19C H -0.1171 -0.0020 0.0567 0.110 Uiso 1 1 calc R . .
C20A C -0.1170(2) -0.0700(6) -0.0996(2) 0.090(2) Uani 1 1 d . . .
H20C H -0.1381 -0.0645 -0.1251 0.135 Uiso 1 1 calc R . .
H20D H -0.1103 -0.1387 -0.0941 0.135 Uiso 1 1 calc R . .
H20E H -0.0963 -0.0341 -0.1026 0.135 Uiso 1 1 calc R . .
C23C C 0.26144(17) 0.5136(5) 0.0090(2) 0.0578(18) Uani 1 1 d . . .
O5C O 0.28146(12) 0.5891(3) 0.02358(13) 0.0649(12) Uani 1 1 d . . .
O4C O 0.25726(11) 0.4793(3) -0.02670(14) 0.0633(12) Uani 1 1 d . . .
C7A C -0.13249(15) 0.4810(5) -0.0184(2) 0.068(2) Uani 1 1 d . . .
H7AA H -0.1311 0.5345 0.0012 0.082 Uiso 1 1 calc R . .
H7AB H -0.1459 0.5057 -0.0464 0.082 Uiso 1 1 calc R . .
C5A C -0.15354(16) 0.3974(5) -0.0093(2) 0.0556(17) Uani 1 1 d . . .
C6A C -0.16682(16) 0.3896(5) 0.0235(2) 0.0549(17) Uani 1 1 d . . .
C4A C -0.16563(17) 0.3108(5) -0.0333(2) 0.0571(17) Uani 1 1 d . . .
N4A N -0.18517(13) 0.3008(4) 0.01855(17) 0.0589(14) Uani 1 1 d . . .
H4AA H -0.1958 0.2787 0.0354 0.071 Uiso 1 1 calc R . .
N3A N -0.18469(13) 0.2522(4) -0.01572(16) 0.0523(13) Uani 1 1 d . . .
C10A C -0.16348(18) 0.4556(5) 0.0600(2) 0.075(2) Uani 1 1 d . . .
H10B H -0.1499 0.5144 0.0583 0.112 Uiso 1 1 calc R . .
H10C H -0.1505 0.4210 0.0856 0.112 Uiso 1 1 calc R . .
H10D H -0.1879 0.4738 0.0595 0.112 Uiso 1 1 calc R . .
C11A C -0.1588(2) 0.2818(5) -0.0727(2) 0.082(2) Uani 1 1 d . . .
H11A H -0.1704 0.2190 -0.0824 0.122 Uiso 1 1 calc R . .
H11B H -0.1324 0.2764 -0.0670 0.122 Uiso 1 1 calc R . .
H11C H -0.1690 0.3314 -0.0938 0.122 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 O1C 1.951(4) . ?
Co1 O1B 1.987(4) . ?
Co1 N1A 1.999(5) . ?
Co1 N7A 2.009(5) . ?
Co2 N5A 2.036(5) 8_556 ?
Co2 N3A 2.040(5) 8_556 ?
Co2 O5C 2.077(4) 6_566 ?
Co2 O5B 2.161(4) . ?
Co2 O4B 2.200(4) . ?
Co2 O4C 2.289(4) 6_566 ?
Co2 C23C 2.489(7) 6_566 ?
O5B C23B 1.245(7) . ?
O6C C22C 1.343(7) . ?
O3C C3C 1.345(7) . ?
O3C H3CA 0.8200 . ?
O6B C22B 1.356(7) . ?
O6B H6BA 0.8200 . ?
O1B C1B 1.244(7) . ?
O1C C1C 1.284(7) . ?
N2A C3A 1.315(7) . ?
N2A N1A 1.347(6) . ?
N2A H2AA 0.8600 . ?
O2C C1C 1.238(7) . ?
O2B C1B 1.220(7) . ?
O4B C23B 1.269(6) . ?
C21B C20B 1.374(8) . ?
C21B C22B 1.443(8) . ?
C21B C23B 1.469(8) . ?
N1A C1A 1.344(7) . ?
O3B C4B 1.376(8) . ?
O3B H3BA 0.8200 . ?
C1A C2A 1.389(8) . ?
C1A C8A 1.492(9) . ?
C12C C11C 1.517(8) . ?
C12C C13C 1.532(8) . ?
C12C H12A 0.9700 . ?
C12C H12B 0.9700 . ?
C22C C13C 1.384(8) . ?
C22C C21C 1.428(8) . ?
C12B C13B 1.509(9) . ?
C12B C5B 1.510(9) . ?
C12B H12C 0.9700 . ?
C12B H12D 0.9700 . ?
N7A C15A 1.326(8) . ?
N7A N8A 1.341(7) . ?
C11C C3C 1.369(8) . ?
C11C C10C 1.416(9) . ?
C1C C2C 1.493(9) . ?
C2C C4C 1.365(8) . ?
C2C C3C 1.428(8) . ?
C1B C2B 1.485(9) . ?
C18A C13A 1.494(8) . ?
C18A C16A 1.509(8) . ?
C18A H18A 0.9700 . ?
C18A H18B 0.9700 . ?
C16A C17A 1.356(9) . ?
C16A C15A 1.391(8) . ?
C22B C13B 1.380(9) . ?
C10C C9C 1.440(9) . ?
C10C C5C 1.448(9) . ?
C13C C14C 1.426(9) . ?
C19C C20C 1.401(8) . ?
C19C C18C 1.403(10) . ?
C19C C14C 1.406(9) . ?
N8A C17A 1.323(8) . ?
N8A H8AA 0.8600 . ?
C14B C15B 1.404(9) . ?
C14B C19B 1.404(9) . ?
C14B C13B 1.424(9) . ?
C15A C21A 1.522(9) . ?
C14C C15C 1.420(8) . ?
C20C C21C 1.364(8) . ?
C20C H20A 0.9300 . ?
C2B C3B 1.356(9) . ?
C2B C4B 1.405(8) . ?
C5B C4B 1.383(9) . ?
C5B C6B 1.405(10) . ?
C5C C6C 1.407(9) . ?
C5C C4C 1.413(9) . ?
C3A C2A 1.395(8) . ?
C3A C9A 1.491(9) . ?
C15C C16C 1.377(10) . ?
C15C H15A 0.9300 . ?
C9C C8C 1.353(10) . ?
C9C H9CA 0.9300 . ?
C13A C14A 1.356(8) . ?
C13A C12A 1.396(8) . ?
C21C C23C 1.520(8) . ?
C9A H9AA 0.9600 . ?
C9A H9AB 0.9600 . ?
C9A H9AC 0.9600 . ?
C6C C7C 1.384(10) . ?
C6C H6CA 0.9300 . ?
C4C H4CA 0.9300 . ?
C19B C20B 1.391(9) . ?
C19B C18B 1.403(10) . ?
C18B C17B 1.390(12) . ?
C18B H18C 0.9300 . ?
C2A C7A 1.519(8) . ?
C21A H21A 0.9600 . ?
C21A H21B 0.9600 . ?
C21A H21C 0.9600 . ?
C18C C17C 1.399(10) . ?
C18C H18D 0.9300 . ?
C17A C22A 1.511(10) . ?
C7C C8C 1.401(11) . ?
C7C H7CA 0.9300 . ?
C15B C16B 1.360(11) . ?
C15B H15B 0.9300 . ?
C16C C17C 1.371(11) . ?
C16C H16A 0.9300 . ?
C20B H20B 0.9300 . ?
C8C H8CA 0.9300 . ?
C16B C17B 1.392(12) . ?
C16B H16B 0.9300 . ?
C8A H8AB 0.9600 . ?
C8A H8AC 0.9600 . ?
C8A H8AD 0.9600 . ?
C11B C6B 1.408(11) . ?
C11B C10B 1.417(11) . ?
C11B C3B 1.435(10) . ?
C3B H3BB 0.9300 . ?
C17C H17A 0.9300 . ?
C6B C7B 1.417(10) . ?
C10B C9B 1.335(13) . ?
C10B H10A 0.9300 . ?
C22A H22A 0.9600 . ?
C22A H22B 0.9600 . ?
C22A H22C 0.9600 . ?
C17B H17B 0.9300 . ?
C7B C8B 1.362(13) . ?
C7B H7BA 0.9300 . ?
C8B C9B 1.354(14) . ?
C8B H8BA 0.9300 . ?
C9B H9BA 0.9300 . ?
C12A N5A 1.357(7) . ?
C12A C19A 1.457(8) . ?
C14A N6A 1.357(7) . ?
C14A C20A 1.499(8) . ?
N6A N5A 1.359(6) . ?
N6A H6AA 0.8600 . ?
N5A Co2 2.035(5) 8_455 ?
C19A H19A 0.9600 . ?
C19A H19B 0.9600 . ?
C19A H19C 0.9600 . ?
C20A H20C 0.9600 . ?
C20A H20D 0.9600 . ?
C20A H20E 0.9600 . ?
C23C O4C 1.253(7) . ?
C23C O5C 1.267(7) . ?
C23C Co2 2.489(7) 6_565 ?
O5C Co2 2.077(4) 6_565 ?
O4C Co2 2.289(4) 6_565 ?
C7A C5A 1.478(8) . ?
C7A H7AA 0.9700 . ?
C7A H7AB 0.9700 . ?
C5A C6A 1.378(8) . ?
C5A C4A 1.405(8) . ?
C6A N4A 1.367(7) . ?
C6A C10A 1.492(8) . ?
C4A N3A 1.344(7) . ?
C4A C11A 1.500(9) . ?
N4A N3A 1.340(6) . ?
N4A H4AA 0.8600 . ?
N3A Co2 2.040(5) 8_455 ?
C10A H10B 0.9600 . ?
C10A H10C 0.9600 . ?
C10A H10D 0.9600 . ?
C11A H11A 0.9600 . ?
C11A H11B 0.9600 . ?
C11A H11C 0.9600 . ?

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
O1C Co1 O1B 113.52(18) . . ?
O1C Co1 N1A 111.3(2) . . ?
O1B Co1 N1A 101.8(2) . . ?
O1C Co1 N7A 111.4(2) . . ?
O1B Co1 N7A 112.7(2) . . ?
N1A Co1 N7A 105.3(2) . . ?
N5A Co2 N3A 97.69(19) 8_556 8_556 ?
N5A Co2 O5C 108.84(19) 8_556 6_566 ?
N3A Co2 O5C 96.7(2) 8_556 6_566 ?
N5A Co2 O5B 97.50(19) 8_556 . ?
N3A Co2 O5B 103.76(19) 8_556 . ?
O5C Co2 O5B 144.04(17) 6_566 . ?
N5A Co2 O4B 156.93(18) 8_556 . ?
N3A Co2 O4B 86.54(17) 8_556 . ?
O5C Co2 O4B 93.06(17) 6_566 . ?
O5B Co2 O4B 59.56(16) . . ?
N5A Co2 O4C 94.20(17) 8_556 6_566 ?
N3A Co2 O4C 156.74(19) 8_556 6_566 ?
O5C Co2 O4C 60.47(16) 6_566 6_566 ?
O5B Co2 O4C 94.37(16) . 6_566 ?
O4B Co2 O4C 90.31(15) . 6_566 ?
N5A Co2 C23C 105.1(2) 8_556 6_566 ?
N3A Co2 C23C 126.8(2) 8_556 6_566 ?
O5C Co2 C23C 30.55(19) 6_566 6_566 ?
O5B Co2 C23C 119.6(2) . 6_566 ?
O4B Co2 C23C 89.98(18) . 6_566 ?
O4C Co2 C23C 30.04(18) 6_566 6_566 ?
C23B O5B Co2 91.9(4) . . ?
C3C O3C H3CA 109.5 . . ?
C22B O6B H6BA 109.5 . . ?
C1B O1B Co1 106.7(4) . . ?
C1C O1C Co1 129.2(4) . . ?
C3A N2A N1A 113.0(5) . . ?
C3A N2A H2AA 123.5 . . ?
N1A N2A H2AA 123.5 . . ?
C23B O4B Co2 89.5(4) . . ?
C20B C21B C22B 117.9(6) . . ?
C20B C21B C23B 122.9(6) . . ?
C22B C21B C23B 119.3(6) . . ?
C1A N1A N2A 105.0(5) . . ?
C1A N1A Co1 128.0(5) . . ?
N2A N1A Co1 124.4(4) . . ?
C4B O3B H3BA 109.5 . . ?
N1A C1A C2A 110.2(6) . . ?
N1A C1A C8A 121.9(6) . . ?
C2A C1A C8A 127.9(6) . . ?
C11C C12C C13C 115.7(5) . . ?
C11C C12C H12A 108.4 . . ?
C13C C12C H12A 108.4 . . ?
C11C C12C H12B 108.4 . . ?
C13C C12C H12B 108.4 . . ?
H12A C12C H12B 107.4 . . ?
O6C C22C C13C 120.2(6) . . ?
O6C C22C C21C 118.8(6) . . ?
C13C C22C C21C 121.0(6) . . ?
O5B C23B O4B 119.0(5) . . ?
O5B C23B C21B 122.6(6) . . ?
O4B C23B C21B 118.4(6) . . ?
C13B C12B C5B 117.5(6) . . ?
C13B C12B H12C 107.9 . . ?
C5B C12B H12C 107.9 . . ?
C13B C12B H12D 107.9 . . ?
C5B C12B H12D 107.9 . . ?
H12C C12B H12D 107.2 . . ?
C15A N7A N8A 104.2(5) . . ?
C15A N7A Co1 131.7(5) . . ?
N8A N7A Co1 124.0(5) . . ?
C3C C11C C10C 118.9(6) . . ?
C3C C11C C12C 118.3(6) . . ?
C10C C11C C12C 122.7(6) . . ?
O2C C1C O1C 123.2(6) . . ?
O2C C1C C2C 120.7(6) . . ?
O1C C1C C2C 116.1(6) . . ?
C4C C2C C3C 118.6(6) . . ?
C4C C2C C1C 119.0(6) . . ?
C3C C2C C1C 122.4(6) . . ?
O3C C3C C11C 117.3(6) . . ?
O3C C3C C2C 120.8(6) . . ?
C11C C3C C2C 121.8(6) . . ?
O2B C1B O1B 119.8(7) . . ?
O2B C1B C2B 119.8(7) . . ?
O1B C1B C2B 120.0(7) . . ?
C13A C18A C16A 115.2(5) . . ?
C13A C18A H18A 108.5 . . ?
C16A C18A H18A 108.5 . . ?
C13A C18A H18B 108.5 . . ?
C16A C18A H18B 108.5 . . ?
H18A C18A H18B 107.5 . . ?
C17A C16A C15A 105.4(6) . . ?
C17A C16A C18A 127.0(7) . . ?
C15A C16A C18A 127.6(7) . . ?
O6B C22B C13B 118.6(6) . . ?
O6B C22B C21B 120.4(6) . . ?
C13B C22B C21B 121.0(6) . . ?
C11C C10C C9C 123.6(7) . . ?
C11C C10C C5C 120.7(6) . . ?
C9C C10C C5C 115.8(7) . . ?
C22C C13C C14C 119.1(6) . . ?
C22C C13C C12C 116.6(6) . . ?
C14C C13C C12C 124.3(6) . . ?
C20C C19C C18C 119.6(7) . . ?
C20C C19C C14C 120.1(7) . . ?
C18C C19C C14C 120.2(7) . . ?
C17A N8A N7A 113.0(6) . . ?
C17A N8A H8AA 123.5 . . ?
N7A N8A H8AA 123.5 . . ?
C15B C14B C19B 117.4(7) . . ?
C15B C14B C13B 122.5(7) . . ?
C19B C14B C13B 120.1(6) . . ?
N7A C15A C16A 110.7(6) . . ?
N7A C15A C21A 122.2(6) . . ?
C16A C15A C21A 127.1(7) . . ?
C19C C14C C15C 118.4(7) . . ?
C19C C14C C13C 119.3(6) . . ?
C15C C14C C13C 122.3(7) . . ?
C21C C20C C19C 121.1(6) . . ?
C21C C20C H20A 119.5 . . ?
C19C C20C H20A 119.5 . . ?
C3B C2B C4B 118.5(6) . . ?
C3B C2B C1B 119.3(7) . . ?
C4B C2B C1B 122.2(7) . . ?
C4B C5B C6B 118.4(7) . . ?
C4B C5B C12B 119.0(7) . . ?
C6B C5B C12B 122.6(7) . . ?
C22B C13B C14B 119.0(6) . . ?
C22B C13B C12B 119.2(7) . . ?
C14B C13B C12B 121.7(6) . . ?
C6C C5C C4C 120.4(7) . . ?
C6C C5C C10C 122.9(7) . . ?
C4C C5C C10C 116.6(7) . . ?
N2A C3A C2A 106.5(6) . . ?
N2A C3A C9A 123.4(7) . . ?
C2A C3A C9A 130.0(6) . . ?
C16C C15C C14C 120.1(8) . . ?
C16C C15C H15A 119.9 . . ?
C14C C15C H15A 119.9 . . ?
C8C C9C C10C 120.9(7) . . ?
C8C C9C H9CA 119.5 . . ?
C10C C9C H9CA 119.5 . . ?
O3B C4B C5B 118.2(6) . . ?
O3B C4B C2B 118.9(6) . . ?
C5B C4B C2B 122.9(7) . . ?
C14A C13A C12A 105.7(5) . . ?
C14A C13A C18A 127.2(6) . . ?
C12A C13A C18A 127.1(6) . . ?
C20C C21C C22C 119.3(6) . . ?
C20C C21C C23C 119.6(6) . . ?
C22C C21C C23C 121.2(6) . . ?
C3A C9A H9AA 109.5 . . ?
C3A C9A H9AB 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
C3A C9A H9AC 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
C7C C6C C5C 116.9(8) . . ?
C7C C6C H6CA 121.5 . . ?
C5C C6C H6CA 121.5 . . ?
C2C C4C C5C 123.0(6) . . ?
C2C C4C H4CA 118.5 . . ?
C5C C4C H4CA 118.5 . . ?
C20B C19B C18B 118.8(7) . . ?
C20B C19B C14B 119.2(7) . . ?
C18B C19B C14B 121.9(7) . . ?
C17B C18B C19B 118.7(9) . . ?
C17B C18B H18C 120.7 . . ?
C19B C18B H18C 120.7 . . ?
C1A C2A C3A 105.2(6) . . ?
C1A C2A C7A 127.0(7) . . ?
C3A C2A C7A 127.8(6) . . ?
C15A C21A H21A 109.5 . . ?
C15A C21A H21B 109.5 . . ?
H21A C21A H21B 109.5 . . ?
C15A C21A H21C 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
C17C C18C C19C 119.9(9) . . ?
C17C C18C H18D 120.0 . . ?
C19C C18C H18D 120.0 . . ?
N8A C17A C16A 106.6(6) . . ?
N8A C17A C22A 120.3(7) . . ?
C16A C17A C22A 133.0(7) . . ?
C6C C7C C8C 122.2(8) . . ?
C6C C7C H7CA 118.9 . . ?
C8C C7C H7CA 118.9 . . ?
C16B C15B C14B 120.7(8) . . ?
C16B C15B H15B 119.7 . . ?
C14B C15B H15B 119.7 . . ?
C17C C16C C15C 121.5(8) . . ?
C17C C16C H16A 119.2 . . ?
C15C C16C H16A 119.2 . . ?
C21B C20B C19B 122.5(6) . . ?
C21B C20B H20B 118.8 . . ?
C19B C20B H20B 118.8 . . ?
C9C C8C C7C 121.2(7) . . ?
C9C C8C H8CA 119.4 . . ?
C7C C8C H8CA 119.4 . . ?
C15B C16B C17B 121.9(9) . . ?
C15B C16B H16B 119.1 . . ?
C17B C16B H16B 119.1 . . ?
C1A C8A H8AB 109.5 . . ?
C1A C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
C1A C8A H8AD 109.5 . . ?
H8AB C8A H8AD 109.5 . . ?
H8AC C8A H8AD 109.5 . . ?
C6B C11B C10B 120.1(9) . . ?
C6B C11B C3B 118.7(8) . . ?
C10B C11B C3B 121.1(9) . . ?
C2B C3B C11B 121.2(7) . . ?
C2B C3B H3BB 119.4 . . ?
C11B C3B H3BB 119.4 . . ?
C16C C17C C18C 119.8(9) . . ?
C16C C17C H17A 120.1 . . ?
C18C C17C H17A 120.1 . . ?
C5B C6B C11B 120.1(7) . . ?
C5B C6B C7B 123.3(8) . . ?
C11B C6B C7B 116.6(9) . . ?
C9B C10B C11B 120.4(10) . . ?
C9B C10B H10A 119.8 . . ?
C11B C10B H10A 119.8 . . ?
C17A C22A H22A 109.5 . . ?
C17A C22A H22B 109.5 . . ?
H22A C22A H22B 109.5 . . ?
C17A C22A H22C 109.5 . . ?
H22A C22A H22C 109.5 . . ?
H22B C22A H22C 109.5 . . ?
C18B C17B C16B 119.4(9) . . ?
C18B C17B H17B 120.3 . . ?
C16B C17B H17B 120.3 . . ?
C8B C7B C6B 120.4(10) . . ?
C8B C7B H7BA 119.8 . . ?
C6B C7B H7BA 119.8 . . ?
C9B C8B C7B 122.1(10) . . ?
C9B C8B H8BA 118.9 . . ?
C7B C8B H8BA 118.9 . . ?
C10B C9B C8B 120.3(11) . . ?
C10B C9B H9BA 119.8 . . ?
C8B C9B H9BA 119.8 . . ?
N5A C12A C13A 110.7(5) . . ?
N5A C12A C19A 118.7(6) . . ?
C13A C12A C19A 130.5(6) . . ?
C13A C14A N6A 107.7(6) . . ?
C13A C14A C20A 131.8(6) . . ?
N6A C14A C20A 120.4(6) . . ?
C14A N6A N5A 111.4(5) . . ?
C14A N6A H6AA 124.3 . . ?
N5A N6A H6AA 124.3 . . ?
C12A N5A N6A 104.5(5) . . ?
C12A N5A Co2 132.1(4) . 8_455 ?
N6A N5A Co2 122.4(4) . 8_455 ?
C12A C19A H19A 109.5 . . ?
C12A C19A H19B 109.5 . . ?
H19A C19A H19B 109.5 . . ?
C12A C19A H19C 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
C14A C20A H20C 109.5 . . ?
C14A C20A H20D 109.5 . . ?
H20C C20A H20D 109.5 . . ?
C14A C20A H20E 109.5 . . ?
H20C C20A H20E 109.5 . . ?
H20D C20A H20E 109.5 . . ?
O4C C23C O5C 122.2(6) . . ?
O4C C23C C21C 119.0(6) . . ?
O5C C23C C21C 118.9(7) . . ?
O4C C23C Co2 66.1(3) . 6_565 ?
O5C C23C Co2 56.4(3) . 6_565 ?
C21C C23C Co2 172.8(5) . 6_565 ?
C23C O5C Co2 93.0(4) . 6_565 ?
C23C O4C Co2 83.9(4) . 6_565 ?
C5A C7A C2A 113.2(5) . . ?
C5A C7A H7AA 108.9 . . ?
C2A C7A H7AA 108.9 . . ?
C5A C7A H7AB 108.9 . . ?
C2A C7A H7AB 108.9 . . ?
H7AA C7A H7AB 107.7 . . ?
C6A C5A C4A 105.5(6) . . ?
C6A C5A C7A 127.3(7) . . ?
C4A C5A C7A 127.2(7) . . ?
N4A C6A C5A 106.4(6) . . ?
N4A C6A C10A 121.1(6) . . ?
C5A C6A C10A 132.5(6) . . ?
N3A C4A C5A 110.5(6) . . ?
N3A C4A C11A 122.0(6) . . ?
C5A C4A C11A 127.5(6) . . ?
N3A N4A C6A 112.0(5) . . ?
N3A N4A H4AA 124.0 . . ?
C6A N4A H4AA 124.0 . . ?
N4A N3A C4A 105.7(5) . . ?
N4A N3A Co2 121.9(4) . 8_455 ?
C4A N3A Co2 132.4(5) . 8_455 ?
C6A C10A H10B 109.5 . . ?
C6A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
C6A C10A H10D 109.5 . . ?
H10B C10A H10D 109.5 . . ?
H10C C10A H10D 109.5 . . ?
C4A C11A H11A 109.5 . . ?
C4A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C4A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        24.84
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         1.414
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.071
####################################################################### 
# 
# 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_12ssg004
_database_code_depnum_ccdc_archive 'CCDC 1407122'
_audit_update_record             
;
2015-06-16 deposited with the CCDC.
2015-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H26 Co N4 O7'
_chemical_formula_weight         553.43

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   P2(1)/n

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

_cell_length_a                   10.4589(14)
_cell_length_b                   13.3445(17)
_cell_length_c                   18.115(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.25
_cell_angle_gamma                90.00
_cell_volume                     2528.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    19269
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      31.59

_exptl_crystal_description       Cube
_exptl_crystal_colour            Purple
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1148
_exptl_absorpt_coefficient_mu    0.731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.747807
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'SADABS v.2.03 (Bruker, 2001), R(int)=0.0823 before correction'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(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 APEX-2 CCD area detector'
_diffrn_measurement_method       '/w scans'
_diffrn_detector_area_resol_mean 8
_diffrn_reflns_number            36122
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         31.00
_reflns_number_total             7810
_reflns_number_gt                6637
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX-2'
_computing_cell_refinement       'Bruker APEX-2'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0753P)²+1.1134P] 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         7810
_refine_ls_number_parameters     362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1241
_refine_ls_wR_factor_gt          0.1201
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.563665(19) 0.354665(14) 0.062466(11) 0.01666(7) Uani 1 1 d . . .
O1 O 0.65411(12) 0.43415(9) -0.01468(6) 0.0230(2) Uani 1 1 d . . .
N1 N 0.56617(12) 0.46312(9) 0.14005(7) 0.0184(2) Uani 1 1 d . . .
C1 C 0.54577(14) 0.46585(11) 0.21327(8) 0.0191(3) Uani 1 1 d . . .
O1W O 0.4104(6) -0.0606(3) 0.0489(3) 0.1657(19) Uani 1 1 d . . .
N2 N 0.60346(13) 0.55711(10) 0.12053(7) 0.0194(2) Uani 1 1 d . . .
H222 H 0.619(2) 0.5697(16) 0.0751(13) 0.025(5) Uiso 1 1 d . . .
O2 O 0.61676(12) 0.28443(9) -0.06055(7) 0.0259(2) Uani 1 1 d . . .
C2 C 0.57064(14) 0.56243(12) 0.24030(8) 0.0192(3) Uani 1 1 d . . .
N3 N 0.66696(13) 0.24278(9) 0.10632(7) 0.0200(3) Uani 1 1 d . . .
O3 O 0.67992(15) 0.24190(11) -0.19374(8) 0.0390(3) Uani 1 1 d . . .
H3A H 0.6501 0.2329 -0.1525 0.058 Uiso 1 1 calc R . .
C3 C 0.60725(15) 0.61846(12) 0.17925(9) 0.0205(3) Uani 1 1 d . . .
N4 N 0.62106(14) 0.14842(10) 0.11131(9) 0.0254(3) Uani 1 1 d . . .
H444 H 0.542(2) 0.1347(16) 0.0975(13) 0.026(6) Uiso 1 1 d . . .
O4 O 0.38572(11) 0.33066(9) 0.03298(7) 0.0258(2) Uani 1 1 d . . .
C4 C 0.78804(15) 0.23845(11) 0.13043(8) 0.0190(3) Uani 1 1 d . . .
C5 C 0.81819(15) 0.13991(11) 0.15117(9) 0.0195(3) Uani 1 1 d . . .
O5 O 0.37514(12) 0.16802(11) 0.06030(8) 0.0329(3) Uani 1 1 d . . .
O6 O 0.17382(13) 0.06723(10) 0.03105(9) 0.0359(3) Uani 1 1 d . . .
H6A H 0.2467 0.0764 0.0466 0.054 Uiso 1 1 calc R . .
C6 C 0.70852(16) 0.08496(12) 0.13783(10) 0.0241(3) Uani 1 1 d . . .
C7 C 0.94184(15) 0.10034(13) 0.18144(9) 0.0232(3) Uani 1 1 d . . .
H7A H 1.0055 0.1531 0.1802 0.035 Uiso 1 1 calc R . .
H7B H 0.9715 0.0462 0.1502 0.035 Uiso 1 1 calc R . .
C8 C 0.50163(18) 0.37497(13) 0.25372(10) 0.0267(3) Uani 1 1 d . . .
H8A H 0.5061 0.3178 0.2217 0.040 Uiso 1 1 calc R . .
H8B H 0.4150 0.3845 0.2695 0.040 Uiso 1 1 calc R . .
H8C H 0.5554 0.3641 0.2960 0.040 Uiso 1 1 calc R . .
C9 C 0.64453(19) 0.72576(13) 0.17245(10) 0.0294(4) Uani 1 1 d . . .
H9A H 0.6307 0.7478 0.1226 0.044 Uiso 1 1 calc R . .
H9B H 0.7333 0.7332 0.1850 0.044 Uiso 1 1 calc R . .
H9C H 0.5937 0.7655 0.2053 0.044 Uiso 1 1 calc R . .
C10 C 0.86975(17) 0.32984(13) 0.13145(10) 0.0283(3) Uani 1 1 d . . .
H10A H 0.8302 0.3813 0.1022 0.042 Uiso 1 1 calc R . .
H10B H 0.9522 0.3142 0.1115 0.042 Uiso 1 1 calc R . .
H10C H 0.8795 0.3529 0.1813 0.042 Uiso 1 1 calc R . .
C11 C 0.6811(2) -0.02368(14) 0.14830(14) 0.0391(5) Uani 1 1 d . . .
H11A H 0.6077 -0.0421 0.1194 0.059 Uiso 1 1 calc R . .
H11B H 0.6645 -0.0366 0.1995 0.059 Uiso 1 1 calc R . .
H11C H 0.7536 -0.0623 0.1328 0.059 Uiso 1 1 calc R . .
C12 C 0.72046(15) 0.40281(12) -0.13862(9) 0.0209(3) Uani 1 1 d . . .
C13 C 0.72642(17) 0.33568(14) -0.19841(10) 0.0275(3) Uani 1 1 d . . .
C14 C 0.7808(2) 0.36599(18) -0.26493(11) 0.0384(5) Uani 1 1 d . . .
H14A H 0.7851 0.3213 -0.3043 0.046 Uiso 1 1 calc R . .
C15 C 0.8282(2) 0.46192(19) -0.27271(12) 0.0424(5) Uani 1 1 d . . .
H15A H 0.8636 0.4817 -0.3174 0.051 Uiso 1 1 calc R . .
C16 C 0.8232(2) 0.52956(16) -0.21388(12) 0.0372(4) Uani 1 1 d . . .
H16 H 0.853(3) 0.603(2) -0.2228(15) 0.048(7) Uiso 1 1 d . . .
C17 C 0.76902(17) 0.49944(13) -0.14736(10) 0.0275(3) Uani 1 1 d . . .
H17A H 0.7651 0.5444 -0.1082 0.033 Uiso 1 1 calc R . .
C18 C 0.66114(15) 0.37187(12) -0.06803(9) 0.0203(3) Uani 1 1 d . . .
C19 C 0.19467(14) 0.24417(12) 0.00617(8) 0.0202(3) Uani 1 1 d . . .
C20 C 0.12649(16) 0.15391(12) 0.00451(10) 0.0235(3) Uani 1 1 d . . .
C21 C 0.00430(17) 0.15114(14) -0.02648(11) 0.0299(4) Uani 1 1 d . . .
H21 H -0.033(2) 0.089(2) -0.0316(14) 0.040(7) Uiso 1 1 d . . .
C22 C -0.04809(17) 0.23673(16) -0.05546(12) 0.0335(4) Uani 1 1 d . . .
H22 H -0.135(3) 0.231(2) -0.0804(17) 0.056(8) Uiso 1 1 d . . .
C23 C 0.01751(18) 0.32769(15) -0.05369(12) 0.0335(4) Uani 1 1 d . . .
H23 H -0.024(3) 0.389(2) -0.0750(15) 0.044(7) Uiso 1 1 d . . .
C24 C 0.13773(16) 0.33085(13) -0.02209(10) 0.0262(3) Uani 1 1 d . . .
H24A H 0.1814 0.3915 -0.0196 0.031 Uiso 1 1 calc R . .
C25 C 0.32696(14) 0.24718(12) 0.03539(8) 0.0199(3) 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 O4 1.9603(12) . ?
Co1 O1 1.9961(12) . ?
Co1 N3 2.0049(13) . ?
Co1 N1 2.0174(13) . ?
O1 C18 1.2770(19) . ?
N1 C1 1.345(2) . ?
N1 N2 1.3608(17) . ?
C1 C2 1.403(2) . ?
C1 C8 1.491(2) . ?
N2 C3 1.343(2) . ?
N2 H222 0.86(2) . ?
O2 C18 1.2632(19) . ?
C2 C3 1.390(2) . ?
C2 C7 1.511(2) 2_655 ?
N3 C4 1.339(2) . ?
N3 N4 1.3508(18) . ?
O3 C13 1.345(2) . ?
O3 H3A 0.8200 . ?
C3 C9 1.489(2) . ?
N4 C6 1.334(2) . ?
N4 H444 0.88(2) . ?
O4 C25 1.2731(19) . ?
C4 C5 1.403(2) . ?
C4 C10 1.489(2) . ?
C5 C6 1.382(2) . ?
C5 C7 1.499(2) . ?
O5 C25 1.254(2) . ?
O6 C20 1.346(2) . ?
O6 H6A 0.8200 . ?
C6 C11 1.490(2) . ?
C7 C2 1.511(2) 2_645 ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
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 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C17 1.395(2) . ?
C12 C13 1.407(2) . ?
C12 C18 1.482(2) . ?
C13 C14 1.395(3) . ?
C14 C15 1.380(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.398(3) . ?
C15 H15A 0.9300 . ?
C16 C17 1.393(3) . ?
C16 H16 1.05(3) . ?
C17 H17A 0.9300 . ?
C19 C24 1.397(2) . ?
C19 C20 1.400(2) . ?
C19 C25 1.480(2) . ?
C20 C21 1.394(2) . ?
C21 C22 1.370(3) . ?
C21 H21 0.92(3) . ?
C22 C23 1.395(3) . ?
C22 H22 1.02(3) . ?
C23 C24 1.380(2) . ?
C23 H23 1.00(3) . ?
C24 H24A 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 Co1 O1 110.39(5) . . ?
O4 Co1 N3 119.70(5) . . ?
O1 Co1 N3 114.64(5) . . ?
O4 Co1 N1 108.45(5) . . ?
O1 Co1 N1 95.84(5) . . ?
N3 Co1 N1 104.65(5) . . ?
C18 O1 Co1 102.29(10) . . ?
C1 N1 N2 106.15(12) . . ?
C1 N1 Co1 134.82(10) . . ?
N2 N1 Co1 118.89(10) . . ?
N1 C1 C2 109.84(13) . . ?
N1 C1 C8 120.89(14) . . ?
C2 C1 C8 129.27(15) . . ?
C3 N2 N1 111.32(13) . . ?
C3 N2 H222 129.5(15) . . ?
N1 N2 H222 119.2(15) . . ?
C3 C2 C1 105.53(13) . . ?
C3 C2 C7 126.26(14) . 2_655 ?
C1 C2 C7 128.20(14) . 2_655 ?
C4 N3 N4 105.89(12) . . ?
C4 N3 Co1 131.95(11) . . ?
N4 N3 Co1 121.99(10) . . ?
C13 O3 H3A 109.5 . . ?
N2 C3 C2 107.16(13) . . ?
N2 C3 C9 121.83(15) . . ?
C2 C3 C9 131.00(15) . . ?
C6 N4 N3 111.87(14) . . ?
C6 N4 H444 127.6(14) . . ?
N3 N4 H444 120.5(14) . . ?
C25 O4 Co1 126.26(11) . . ?
N3 C4 C5 109.81(13) . . ?
N3 C4 C10 120.70(14) . . ?
C5 C4 C10 129.48(14) . . ?
C6 C5 C4 105.37(14) . . ?
C6 C5 C7 126.25(14) . . ?
C4 C5 C7 128.37(15) . . ?
C20 O6 H6A 109.5 . . ?
N4 C6 C5 107.06(14) . . ?
N4 C6 C11 122.10(15) . . ?
C5 C6 C11 130.84(16) . . ?
C5 C7 C2 112.54(13) . 2_645 ?
C5 C7 H7A 109.1 . . ?
C2 C7 H7A 109.1 2_645 . ?
C5 C7 H7B 109.1 . . ?
C2 C7 H7B 109.1 2_645 . ?
H7A C7 H7B 107.8 . . ?
C1 C8 H8A 109.5 . . ?
C1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C3 C9 H9A 109.5 . . ?
C3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 118.93(16) . . ?
C17 C12 C18 120.62(15) . . ?
C13 C12 C18 120.44(15) . . ?
O3 C13 C14 118.23(17) . . ?
O3 C13 C12 121.77(16) . . ?
C14 C13 C12 120.00(18) . . ?
C15 C14 C13 120.34(19) . . ?
C15 C14 H14A 119.8 . . ?
C13 C14 H14A 119.8 . . ?
C14 C15 C16 120.44(19) . . ?
C14 C15 H15A 119.8 . . ?
C16 C15 H15A 119.8 . . ?
C17 C16 C15 119.32(19) . . ?
C17 C16 H16 121.9(15) . . ?
C15 C16 H16 118.6(15) . . ?
C16 C17 C12 120.97(18) . . ?
C16 C17 H17A 119.5 . . ?
C12 C17 H17A 119.5 . . ?
O2 C18 O1 119.85(15) . . ?
O2 C18 C12 120.34(14) . . ?
O1 C18 C12 119.81(14) . . ?
C24 C19 C20 119.22(14) . . ?
C24 C19 C25 120.33(14) . . ?
C20 C19 C25 120.42(14) . . ?
O6 C20 C21 117.13(15) . . ?
O6 C20 C19 123.03(15) . . ?
C21 C20 C19 119.83(16) . . ?
C22 C21 C20 119.77(17) . . ?
C22 C21 H21 122.8(16) . . ?
C20 C21 H21 117.0(16) . . ?
C21 C22 C23 121.38(17) . . ?
C21 C22 H22 117.6(17) . . ?
C23 C22 H22 121.0(17) . . ?
C24 C23 C22 118.91(17) . . ?
C24 C23 H23 121.7(16) . . ?
C22 C23 H23 119.4(16) . . ?
C23 C24 C19 120.85(16) . . ?
C23 C24 H24A 119.6 . . ?
C19 C24 H24A 119.6 . . ?
O5 C25 O4 123.81(14) . . ?
O5 C25 C19 118.66(14) . . ?
O4 C25 C19 117.53(14) . . ?

_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_theta_full        31.00
_diffrn_measured_fraction_theta_full 0.969
_refine_diff_density_max         0.888
_refine_diff_density_min         -1.116
_refine_diff_density_rms         0.082
####################################################################### 
# 
# 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_monoc
_database_code_depnum_ccdc_archive 'CCDC 1407123'
_audit_update_record             
;
2015-06-16 deposited with the CCDC.
2015-08-24 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 H20 Co N4 O4'
_chemical_formula_weight         427.32

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                   19.2342(13)
_cell_length_b                   13.4738(10)
_cell_length_c                   18.5923(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.139(2)
_cell_angle_gamma                90.00
_cell_volume                     4325.6(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    13995
_cell_measurement_theta_min      2.359
_cell_measurement_theta_max      31.35

_exptl_crystal_description       Prism
_exptl_crystal_colour            Purple
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1768
_exptl_absorpt_coefficient_mu    0.823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7512
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'SADABS v.2.03 (Bruker, 2001), wR2(int) =0.1242 before correction'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(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 APEX-2 CCD area detector'
_diffrn_measurement_method       '/w scans'
_diffrn_detector_area_resol_mean 8
_diffrn_reflns_number            30203
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_sigmaI/netI    0.0654
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         30.00
_reflns_number_total             6133
_reflns_number_gt                2955
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX-2'
_computing_cell_refinement       'Bruker APEX-2'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6133
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2186
_refine_ls_R_factor_gt           0.1240
_refine_ls_wR_factor_ref         0.3184
_refine_ls_wR_factor_gt          0.2969
_refine_ls_goodness_of_fit_ref   1.675
_refine_ls_restrained_S_all      1.675
_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 0.05157(4) 0.28208(7) 0.05482(4) 0.0691(4) Uani 1 1 d . . .
N1 N 0.1203(2) 0.4723(5) 0.1207(3) 0.0708(14) Uani 1 1 d . . .
H1A H 0.1070 0.4920 0.0723 0.085 Uiso 1 1 calc R . .
N2 N 0.1071(2) 0.3815(4) 0.1394(3) 0.0691(14) Uani 1 1 d . . .
C3 C 0.1374(3) 0.3798(6) 0.2210(3) 0.0732(19) Uani 1 1 d . . .
C2 C 0.1706(3) 0.4732(6) 0.2510(3) 0.080(2) Uani 1 1 d . . .
N3 N 0.1151(3) 0.1563(5) 0.0889(3) 0.0767(16) Uani 1 1 d . . .
C5 C 0.2135(4) 0.0499(7) 0.1352(3) 0.090(2) Uani 1 1 d . . .
C8 C 0.1733(5) 0.6387(7) 0.1781(4) 0.126(4) Uani 1 1 d . . .
H8A H 0.2005 0.6674 0.2304 0.189 Uiso 1 1 calc R . .
H8B H 0.1252 0.6731 0.1492 0.189 Uiso 1 1 calc R . .
H8C H 0.2043 0.6443 0.1496 0.189 Uiso 1 1 calc R . .
C9 C 0.1312(4) 0.2894(6) 0.2632(4) 0.092(2) Uani 1 1 d . . .
H9A H 0.1045 0.2385 0.2248 0.139 Uiso 1 1 calc R . .
H9B H 0.1028 0.3046 0.2934 0.139 Uiso 1 1 calc R . .
H9C H 0.1821 0.2665 0.2989 0.139 Uiso 1 1 calc R . .
N4 N 0.0892(3) 0.0696(5) 0.1037(3) 0.0827(16) Uani 1 1 d . . .
H4A H 0.0425 0.0599 0.0967 0.099 Uiso 1 1 calc R . .
C4B C -0.1976(4) 0.3227(8) 0.0064(4) 0.097(3) Uani 1 1 d . . .
H4BA H -0.1622 0.3721 0.0109 0.117 Uiso 1 1 calc R . .
C2B C -0.1728(4) 0.2228(8) 0.0233(4) 0.091(2) Uani 1 1 d . . .
O1A O 0.0716(3) 0.4707(5) -0.0414(3) 0.1003(16) Uani 1 1 d . . .
C1 C 0.1573(3) 0.5307(6) 0.1860(4) 0.084(2) Uani 1 1 d . . .
C4 C 0.1926(3) 0.1460(6) 0.1094(3) 0.077(2) Uani 1 1 d . . .
C6 C 0.1457(4) -0.0010(6) 0.1308(3) 0.082(2) Uani 1 1 d . . .
O2A O 0.0481(4) 0.3147(6) -0.0474(3) 0.1161(19) Uani 1 1 d . . .
C1A C 0.0512(4) 0.3929(7) -0.0746(4) 0.0769(18) Uani 1 1 d . . .
O1B O -0.0623(3) 0.1145(6) 0.0669(4) 0.130(2) Uani 1 1 d . . .
C2A C 0.0233(4) 0.3894(7) -0.1675(4) 0.091(2) Uani 1 1 d . . .
C10 C 0.2385(5) 0.2262(8) 0.1008(5) 0.125(4) Uani 1 1 d . . .
H10A H 0.2910 0.2044 0.1189 0.187 Uiso 1 1 calc R . .
H10B H 0.2371 0.2819 0.1324 0.187 Uiso 1 1 calc R . .
H10C H 0.2177 0.2455 0.0456 0.187 Uiso 1 1 calc R . .
C7 C 0.2088(4) 0.5023(7) 0.3393(4) 0.106(3) Uani 1 1 d . . .
H7A H 0.1751 0.5479 0.3494 0.159 Uiso 1 1 calc R . .
H7B H 0.2147 0.4434 0.3716 0.159 Uiso 1 1 calc R . .
O2B O -0.0498(3) 0.2639(6) 0.0456(5) 0.129(3) Uani 1 1 d . . .
C3A C 0.0126(4) 0.4751(7) -0.2076(3) 0.092(2) Uani 1 1 d . . .
H3AA H 0.0217 0.5350 -0.1800 0.138 Uiso 1 1 calc R . .
C3B C -0.2787(4) 0.3484(8) -0.0179(4) 0.105(3) Uani 1 1 d . . .
H3BA H -0.2955 0.4138 -0.0292 0.157 Uiso 1 1 calc R . .
C1B C -0.0835(5) 0.2049(10) 0.0490(4) 0.096(3) Uani 1 1 d . . .
C4A C 0.0122(5) 0.3006(8) -0.2074(5) 0.107(3) Uani 1 1 d . . .
H4AA H 0.0204 0.2410 -0.1796 0.160 Uiso 1 1 calc R . .
C11 C 0.1332(6) -0.0986(7) 0.1516(5) 0.130(3) Uani 1 1 d . . .
H11A H 0.0798 -0.1062 0.1404 0.195 Uiso 1 1 calc R . .
H11B H 0.1653 -0.1097 0.2076 0.195 Uiso 1 1 calc R . .
H11C H 0.1461 -0.1458 0.1207 0.195 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 O2B 1.897(5) . ?
Co1 O2A 1.922(6) . ?
Co1 N2 1.982(5) . ?
Co1 N3 2.021(6) . ?
N1 N2 1.327(7) . ?
N1 C1 1.357(8) . ?
N1 H1A 0.8600 . ?
N2 C3 1.364(6) . ?
C3 C2 1.410(9) . ?
C3 C9 1.483(9) . ?
C2 C1 1.361(9) . ?
C2 C7 1.525(8) . ?
N3 N4 1.345(8) . ?
N3 C4 1.372(7) . ?
C5 C4 1.378(10) . ?
C5 C6 1.445(10) . ?
C5 C7 1.498(9) 4_545 ?
C8 C1 1.508(11) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
N4 C6 1.362(8) . ?
N4 H4A 0.8600 . ?
C4B C2B 1.416(12) . ?
C4B C3B 1.462(10) . ?
C4B H4BA 0.9300 . ?
C2B C3B 1.310(11) 7_455 ?
C2B C1B 1.586(11) . ?
O1A C1A 1.192(8) . ?
C4 C10 1.448(11) . ?
C6 C11 1.420(11) . ?
O2A C1A 1.181(8) . ?
C1A C2A 1.567(9) . ?
O1B C1B 1.281(11) . ?
C2A C3A 1.339(11) . ?
C2A C4A 1.374(11) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C7 C5 1.498(9) 4 ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
O2B C1B 1.045(11) . ?
C3A C3A 1.432(11) 2_554 ?
C3A H3AA 0.9300 . ?
C3B C2B 1.310(11) 7_455 ?
C3B H3BA 0.9300 . ?
C4A C4A 1.440(15) 2_554 ?
C4A H4AA 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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
O2B Co1 O2A 110.7(3) . . ?
O2B Co1 N2 109.4(2) . . ?
O2A Co1 N2 113.7(3) . . ?
O2B Co1 N3 112.1(3) . . ?
O2A Co1 N3 104.7(3) . . ?
N2 Co1 N3 106.1(2) . . ?
N2 N1 C1 112.6(5) . . ?
N2 N1 H1A 123.7 . . ?
C1 N1 H1A 123.7 . . ?
N1 N2 C3 105.7(5) . . ?
N1 N2 Co1 120.9(3) . . ?
C3 N2 Co1 133.5(5) . . ?
N2 C3 C2 108.8(6) . . ?
N2 C3 C9 120.5(6) . . ?
C2 C3 C9 130.6(5) . . ?
C1 C2 C3 106.3(5) . . ?
C1 C2 C7 128.5(7) . . ?
C3 C2 C7 125.1(6) . . ?
N4 N3 C4 108.1(5) . . ?
N4 N3 Co1 124.4(4) . . ?
C4 N3 Co1 127.2(5) . . ?
C4 C5 C6 107.9(6) . . ?
C4 C5 C7 127.6(7) . 4_545 ?
C6 C5 C7 124.4(8) . 4_545 ?
C1 C8 H8A 109.5 . . ?
C1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C3 C9 H9A 109.5 . . ?
C3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 N4 C6 112.1(6) . . ?
N3 N4 H4A 124.0 . . ?
C6 N4 H4A 124.0 . . ?
C2B C4B C3B 120.2(8) . . ?
C2B C4B H4BA 119.9 . . ?
C3B C4B H4BA 119.9 . . ?
C3B C2B C4B 121.3(8) 7_455 . ?
C3B C2B C1B 123.5(10) 7_455 . ?
C4B C2B C1B 115.2(8) . . ?
N1 C1 C2 106.5(6) . . ?
N1 C1 C8 121.4(6) . . ?
C2 C1 C8 132.0(6) . . ?
N3 C4 C5 107.9(6) . . ?
N3 C4 C10 122.3(7) . . ?
C5 C4 C10 129.8(6) . . ?
N4 C6 C11 123.1(8) . . ?
N4 C6 C5 104.0(7) . . ?
C11 C6 C5 132.9(8) . . ?
C1A O2A Co1 129.9(6) . . ?
O2A C1A O1A 129.0(8) . . ?
O2A C1A C2A 112.9(8) . . ?
O1A C1A C2A 118.1(7) . . ?
C3A C2A C4A 120.1(7) . . ?
C3A C2A C1A 118.8(7) . . ?
C4A C2A C1A 121.1(8) . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C7 C2 113.0(5) 4 . ?
C5 C7 H7A 109.0 4 . ?
C2 C7 H7A 109.0 . . ?
C5 C7 H7B 109.0 4 . ?
C2 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C1B O2B Co1 137.1(9) . . ?
C2A C3A C3A 120.5(4) . 2_554 ?
C2A C3A H3AA 119.8 . . ?
C3A C3A H3AA 119.8 2_554 . ?
C2B C3B C4B 118.5(9) 7_455 . ?
C2B C3B H3BA 120.7 7_455 . ?
C4B C3B H3BA 120.7 . . ?
O2B C1B O1B 127.2(10) . . ?
O2B C1B C2B 118.9(11) . . ?
O1B C1B C2B 113.7(10) . . ?
C2A C4A C4A 119.4(5) . 2_554 ?
C2A C4A H4AA 120.3 . . ?
C4A C4A H4AA 120.3 2_554 . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         1.375
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.147
