# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_12sbj044_0m
_database_code_depnum_ccdc_archive 'CCDC 1434962'
_audit_update_record             
;
2015-11-03 deposited with the CCDC.
2016-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H24 Co N6 O6'
_chemical_formula_weight         623.48

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'

_space_group_crystal_system      tetragonal
_space_group_IT_number           122
_space_group_name_H-M_alt        'I -4 2 d'
_space_group_name_Hall           'I -4 2bw'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'-x+1/2, y, -z+3/4'
'x+1/2, -y, -z+3/4'
'-y+1/2, -x, z+3/4'
'y+1/2, x, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'
'-x+1, y+1/2, -z+5/4'
'x+1, -y+1/2, -z+5/4'
'-y+1, -x+1/2, z+5/4'
'y+1, x+1/2, z+5/4'

_cell_length_a                   25.1433(7)
_cell_length_b                   25.1433(7)
_cell_length_c                   10.6879(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6756.7(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    11325
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      27.47

_exptl_crystal_description       Block
_exptl_crystal_colour            Purple
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_F_000             2568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    0.554
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8526
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
'SADABS v.2.03 (Bruker, 2001), wR2(int)=0.0894 before correction'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-2 CCD area detector'
_diffrn_measurement_method       '/w scans'
_diffrn_detector_area_resol_mean 8
_diffrn_reflns_number            46664
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.620
_diffrn_reflns_theta_max         25.416
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3100
_reflns_number_gt                2842
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.810
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.998

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX-2'
_computing_cell_refinement       'Bruker APEX-2'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0862P)²+0.9434P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1207 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.012(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3100
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1174
_refine_ls_wR_factor_gt          0.1120
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.43964(3) 0.2500 0.1250 0.0306(2) Uani 1 2 d S T P . .
O2 O 0.37736(11) 0.21775(12) 0.0083(3) 0.0436(7) Uani 1 1 d . . . . .
O1 O 0.50123(11) 0.22531(12) 0.0039(3) 0.0441(7) Uani 1 1 d . . . . .
O3 O 0.55576(12) 0.28852(11) -0.0667(3) 0.0446(8) Uani 1 1 d . . . . .
N3 N 0.34855(12) 0.14639(13) 0.1196(4) 0.0368(7) Uani 1 1 d . . . . .
H333 H 0.3222 0.1252 0.1308 0.044 Uiso 1 1 calc R U . . .
C7 C 0.54685(15) 0.24338(16) -0.0185(4) 0.0345(9) Uani 1 1 d . . . . .
C12 C 0.34380(15) 0.18290(16) 0.0302(4) 0.0347(9) Uani 1 1 d . . . . .
C13 C 0.29489(15) 0.17998(15) -0.0492(4) 0.0338(9) Uani 1 1 d . . . . .
C11 C 0.39327(15) 0.13963(16) 0.1975(4) 0.0345(9) Uani 1 1 d . . . . .
C15 C 0.24427(18) 0.17920(18) 0.0039(4) 0.0460(10) Uani 1 1 d . . . . .
H15 H 0.2405 0.1778 0.0904 0.069 Uiso 1 1 calc R U . . .
C10 C 0.40295(18) 0.09574(16) 0.2724(5) 0.0434(10) Uani 1 1 d . . . . .
H10 H 0.3822 0.0653 0.2807 0.052 Uiso 1 1 calc R U . . .
C14 C 0.30028(18) 0.1805(2) -0.1782(5) 0.0499(12) Uani 1 1 d . . . . .
H14 H 0.3340 0.1817 -0.2139 0.075 Uiso 1 1 calc R U . . .
C6 C 0.63563(16) 0.22540(19) 0.0873(4) 0.0444(11) Uani 1 1 d . . . . .
C1 C 0.59413(16) 0.20905(18) 0.0071(4) 0.0407(10) Uani 1 1 d . . . . .
C5 C 0.68051(19) 0.1925(2) 0.0942(5) 0.0589(14) Uani 1 1 d . . . . .
H5 H 0.7082 0.2020 0.1475 0.071 Uiso 1 1 calc R U . . .
C3 C 0.6442(3) 0.1316(2) -0.0522(6) 0.0679(17) Uani 1 1 d . . . . .
H3 H 0.6471 0.1006 -0.0992 0.082 Uiso 1 1 calc R U . . .
C2 C 0.5986(2) 0.1623(2) -0.0602(5) 0.0533(12) Uani 1 1 d . . . . .
H2 H 0.5708 0.1514 -0.1113 0.064 Uiso 1 1 calc R U . . .
C4 C 0.6849(2) 0.1466(3) 0.0245(6) 0.0687(16) Uani 1 1 d . . . . .
H4 H 0.7155 0.1260 0.0297 0.082 Uiso 1 1 calc R U . . .
N1 N 0.43137(12) 0.17607(13) 0.2089(3) 0.0345(7) Uani 1 1 d . . . . .
N2 N 0.46567(14) 0.15516(14) 0.2918(4) 0.0413(9) Uani 1 1 d . . . . .
H222 H 0.4943 0.1707 0.3164 0.050 Uiso 1 1 calc R U . . .
C9 C 0.44982(18) 0.10706(17) 0.3315(5) 0.0462(11) Uani 1 1 d . . . . .
C8 C 0.4810(2) 0.0768(2) 0.4278(6) 0.0693(17) Uani 1 1 d . . . . .
H8A H 0.5127 0.0961 0.4482 0.104 Uiso 1 1 calc R U . . .
H8B H 0.4903 0.0425 0.3950 0.104 Uiso 1 1 calc R U . . .
H8C H 0.4597 0.0723 0.5017 0.104 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N1 2.074(3) . ?
Co1 N1 2.074(3) 14_454 ?
Co1 O1 2.111(3) 14_454 ?
Co1 O1 2.111(3) . ?
Co1 O2 2.160(3) 14_454 ?
Co1 O2 2.160(3) . ?
O2 C12 1.239(5) . ?
O1 C7 1.257(5) . ?
O3 C7 1.266(5) . ?
N3 C12 1.331(5) . ?
N3 C11 1.409(5) . ?
N3 H333 0.8600 . ?
C7 C1 1.494(5) . ?
C12 C13 1.496(6) . ?
C13 C14 1.385(6) . ?
C13 C15 1.394(6) . ?
C11 N1 1.331(5) . ?
C11 C10 1.385(6) . ?
C15 C14 1.382(7) 5_554 ?
C15 H15 0.9300 . ?
C10 C9 1.367(7) . ?
C10 H10 0.9300 . ?
C14 C15 1.383(7) 5_554 ?
C14 H14 0.9300 . ?
C6 C5 1.401(6) . ?
C6 C1 1.411(6) . ?
C6 C6 1.476(10) 14_454 ?
C1 C2 1.382(7) . ?
C5 C4 1.379(8) . ?
C5 H5 0.9300 . ?
C3 C4 1.364(9) . ?
C3 C2 1.385(8) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C4 H4 0.9300 . ?
N1 N2 1.343(5) . ?
N2 C9 1.342(6) . ?
N2 H222 0.8600 . ?
C9 C8 1.501(6) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 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
N1 Co1 N1 168.50(18) . 14_454 ?
N1 Co1 O1 94.12(13) . 14_454 ?
N1 Co1 O1 94.31(13) 14_454 14_454 ?
N1 Co1 O1 94.31(13) . . ?
N1 Co1 O1 94.12(13) 14_454 . ?
O1 Co1 O1 85.65(18) 14_454 . ?
N1 Co1 O2 90.80(12) . 14_454 ?
N1 Co1 O2 80.84(12) 14_454 14_454 ?
O1 Co1 O2 93.86(12) 14_454 14_454 ?
O1 Co1 O2 174.89(12) . 14_454 ?
N1 Co1 O2 80.84(12) . . ?
N1 Co1 O2 90.80(12) 14_454 . ?
O1 Co1 O2 174.89(12) 14_454 . ?
O1 Co1 O2 93.86(12) . . ?
O2 Co1 O2 87.07(18) 14_454 . ?
C12 O2 Co1 130.6(3) . . ?
C7 O1 Co1 132.8(3) . . ?
C12 N3 C11 125.4(3) . . ?
C12 N3 H333 117.3 . . ?
C11 N3 H333 117.3 . . ?
O1 C7 O3 124.3(4) . . ?
O1 C7 C1 118.8(4) . . ?
O3 C7 C1 116.9(3) . . ?
O2 C12 N3 124.2(4) . . ?
O2 C12 C13 119.2(4) . . ?
N3 C12 C13 116.6(3) . . ?
C14 C13 C15 119.7(4) . . ?
C14 C13 C12 118.9(4) . . ?
C15 C13 C12 121.4(4) . . ?
N1 C11 C10 111.6(4) . . ?
N1 C11 N3 123.1(3) . . ?
C10 C11 N3 125.3(4) . . ?
C14 C15 C13 120.1(4) 5_554 . ?
C14 C15 H15 120.0 5_554 . ?
C13 C15 H15 120.0 . . ?
C9 C10 C11 104.6(4) . . ?
C9 C10 H10 127.7 . . ?
C11 C10 H10 127.7 . . ?
C15 C14 C13 120.2(4) 5_554 . ?
C15 C14 H14 119.9 5_554 . ?
C13 C14 H14 119.9 . . ?
C5 C6 C1 117.1(5) . . ?
C5 C6 C6 117.7(4) . 14_454 ?
C1 C6 C6 125.1(3) . 14_454 ?
C2 C1 C6 120.2(4) . . ?
C2 C1 C7 117.4(4) . . ?
C6 C1 C7 122.1(4) . . ?
C4 C5 C6 122.0(5) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C4 C3 C2 120.2(5) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C1 C2 C3 120.7(5) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C3 C4 C5 119.7(5) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C11 N1 N2 104.7(3) . . ?
C11 N1 Co1 130.5(3) . . ?
N2 N1 Co1 124.9(3) . . ?
C9 N2 N1 111.7(4) . . ?
C9 N2 H222 124.1 . . ?
N1 N2 H222 124.1 . . ?
N2 C9 C10 107.3(4) . . ?
N2 C9 C8 121.3(4) . . ?
C10 C9 C8 131.3(4) . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_refine_diff_density_max         0.567
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.100

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_12sbj045_0m
_database_code_depnum_ccdc_archive 'CCDC 1434963'
_audit_update_record             
;
2015-11-03 deposited with the CCDC.
2016-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 Co N3 O9'
_chemical_formula_weight         551.34

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)/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                   14.5169(9)
_cell_length_b                   9.0637(6)
_cell_length_c                   18.5938(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.689(2)
_cell_angle_gamma                90.00
_cell_volume                     2446.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8470
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      32.012

_exptl_crystal_description       Purple
_exptl_crystal_colour            Block
_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    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1128
_exptl_absorpt_coefficient_mu    0.760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6590
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'SADABS v.2.03 (Bruker, 2001),wR2(int)=0.1441 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            30966
_diffrn_reflns_av_R_equivalents  0.1568
_diffrn_reflns_av_sigmaI/netI    0.1673
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.40
_diffrn_reflns_theta_max         30.00
_reflns_number_total             6953
_reflns_number_gt                3560
_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         6953
_refine_ls_number_parameters     333
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1978
_refine_ls_R_factor_gt           0.1178
_refine_ls_wR_factor_ref         0.3280
_refine_ls_wR_factor_gt          0.2818
_refine_ls_goodness_of_fit_ref   1.434
_refine_ls_restrained_S_all      1.434
_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 0.21942(5) 0.97259(8) 0.48531(4) 0.0181(3) Uani 1 1 d . . .
O6 O 0.1425(3) 1.1718(4) 0.4888(2) 0.0206(9) Uani 1 1 d . . .
O5 O 0.2962(3) 0.7865(4) 0.4849(2) 0.0276(10) Uani 1 1 d . . .
C18 C 0.0375(4) 0.9775(6) 0.3994(3) 0.0165(11) Uani 1 1 d . . .
O3 O 0.5179(3) 0.2757(5) 0.6433(2) 0.0304(11) Uani 1 1 d . . .
N3 N 0.0128(3) 1.1196(5) 0.4244(2) 0.0175(10) Uani 1 1 d . . .
H3A H -0.0410 1.1514 0.4122 0.021 Uiso 1 1 calc R . .
N2 N 0.1161(3) 0.7808(5) 0.3831(3) 0.0213(10) Uani 1 1 d . . .
H2A H 0.1600 0.7173 0.3852 0.026 Uiso 1 1 calc R . .
O4 O 0.2357(3) 0.5883(4) 0.4327(2) 0.0263(10) Uani 1 1 d . . .
N1 N 0.1131(3) 0.9081(5) 0.4219(3) 0.0201(10) Uani 1 1 d . . .
O1S O 0.3074(3) 1.0826(4) 0.4212(2) 0.0289(10) Uani 1 1 d . . .
C20 C 0.0285(4) 1.3594(6) 0.4822(3) 0.0187(11) Uani 1 1 d . . .
C9 C 0.4810(5) 0.5244(6) 0.6015(3) 0.0263(13) Uani 1 1 d . . .
H9A H 0.5324 0.5653 0.6241 0.032 Uiso 1 1 calc R . .
C11 C 0.3499(4) 0.5557(6) 0.5241(3) 0.0199(12) Uani 1 1 d . . .
C12 C 0.3309(4) 0.4014(6) 0.5303(3) 0.0222(12) Uani 1 1 d . . .
H12A H 0.2808 0.3599 0.5060 0.027 Uiso 1 1 calc R . .
C19 C 0.0655(4) 1.2100(6) 0.4655(3) 0.0187(12) Uani 1 1 d . . .
C22 C 0.0725(4) 1.4360(6) 0.5371(3) 0.0216(12) Uani 1 1 d . . .
H22A H 0.1213 1.3927 0.5621 0.032 Uiso 1 1 calc R . .
C2 C 0.6973(4) 0.3753(6) 0.8103(3) 0.0200(12) Uani 1 1 d . . .
C6 C 0.6592(4) 0.2426(6) 0.7021(3) 0.0246(13) Uani 1 1 d . . .
H6A H 0.6743 0.1755 0.6663 0.030 Uiso 1 1 calc R . .
C21 C -0.0437(4) 1.4220(6) 0.4449(3) 0.0217(12) Uani 1 1 d . . .
C13 C 0.3870(4) 0.3160(6) 0.5722(3) 0.0277(13) Uani 1 1 d . . .
H13A H 0.3748 0.2158 0.5770 0.033 Uiso 1 1 calc R . .
C17 C -0.0115(4) 0.8977(6) 0.3498(3) 0.0193(12) Uani 1 1 d . . .
H17A H -0.0666 0.9237 0.3272 0.023 Uiso 1 1 calc R . .
C10 C 0.4224(4) 0.6122(6) 0.5610(3) 0.0226(13) Uani 1 1 d . . .
H10A H 0.4332 0.7133 0.5590 0.027 Uiso 1 1 calc R . .
C14 C 0.2897(4) 0.6515(6) 0.4775(3) 0.0210(12) Uani 1 1 d . . .
C5 C 0.5761(4) 0.3164(6) 0.6996(3) 0.0227(13) Uani 1 1 d . . .
C4 C 0.5521(4) 0.4205(6) 0.7493(3) 0.0247(13) Uani 1 1 d . . .
H4A H 0.4959 0.4696 0.7462 0.030 Uiso 1 1 calc R . .
C3 C 0.6151(4) 0.4508(6) 0.8051(3) 0.0237(13) Uani 1 1 d . . .
H3B H 0.6012 0.5227 0.8390 0.028 Uiso 1 1 calc R . .
C7 C 0.7193(4) 0.2697(6) 0.7580(3) 0.0222(12) Uani 1 1 d . . .
H7A H 0.7746 0.2181 0.7612 0.027 Uiso 1 1 calc R . .
C8 C 0.4629(4) 0.3786(6) 0.6080(3) 0.0232(13) Uani 1 1 d . . .
C16 C 0.0395(4) 0.7683(6) 0.3404(3) 0.0215(12) Uani 1 1 d . . .
C15 C 0.0271(5) 0.6427(7) 0.2915(4) 0.0310(15) Uani 1 1 d . . .
H15A H 0.0279 0.6768 0.2427 0.047 Uiso 1 1 calc R . .
H15B H -0.0309 0.5958 0.3008 0.047 Uiso 1 1 calc R . .
H15C H 0.0762 0.5731 0.2992 0.047 Uiso 1 1 calc R . .
O1W O 0.2730(5) 0.3332(5) 0.3570(3) 0.0558(16) Uani 1 1 d . . .
O2S O 0.2224(5) 0.2608(7) 0.2102(4) 0.080(2) Uani 1 1 d . . .
C2S C 0.2453(10) 0.1140(12) 0.2162(6) 0.087(4) Uani 1 1 d . . .
C1S C 0.4059(4) 1.0688(7) 0.4219(4) 0.0361(17) Uani 1 1 d . . .
H1SA H 0.4313 1.1323 0.3859 0.054 Uiso 1 1 calc R . .
H1SB H 0.4225 0.9684 0.4119 0.054 Uiso 1 1 calc R . .
H1SC H 0.4297 1.0965 0.4684 0.054 Uiso 1 1 calc R . .
O1 O 0.7434(4) 0.5137(5) 0.9128(2) 0.0345(11) Uani 1 1 d . . .
O2 O 0.8333(3) 0.3287(5) 0.8765(2) 0.0307(10) Uani 1 1 d . . .
C1 C 0.7626(4) 0.4043(6) 0.8704(3) 0.0228(13) 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 O1 1.999(5) 2_656 ?
Co1 N1 2.017(4) . ?
Co1 O1S 2.021(4) . ?
Co1 O5 2.022(4) . ?
Co1 O6 2.124(4) . ?
O6 C19 1.244(6) . ?
O5 C14 1.236(6) . ?
C18 N1 1.329(7) . ?
C18 C17 1.366(7) . ?
C18 N3 1.416(7) . ?
O3 C5 1.388(6) . ?
O3 C8 1.388(6) . ?
N3 C19 1.351(7) . ?
N3 H3A 0.8600 . ?
N2 N1 1.362(6) . ?
N2 C16 1.363(7) . ?
N2 H2A 0.8600 . ?
O4 C14 1.273(7) . ?
O1S C1S 1.434(8) . ?
C20 C21 1.373(8) . ?
C20 C22 1.384(8) . ?
C20 C19 1.491(7) . ?
C9 C8 1.354(8) . ?
C9 C10 1.382(8) . ?
C9 H9A 0.9300 . ?
C11 C10 1.350(8) . ?
C11 C12 1.430(7) . ?
C11 C14 1.500(8) . ?
C12 C13 1.361(8) . ?
C12 H12A 0.9300 . ?
C22 C21 1.395(7) 3_586 ?
C22 H22A 0.9300 . ?
C2 C3 1.378(8) . ?
C2 C7 1.405(8) . ?
C2 C1 1.480(8) . ?
C6 C7 1.370(8) . ?
C6 C5 1.380(8) . ?
C6 H6A 0.9300 . ?
C21 C22 1.395(7) 3_586 ?
C13 C8 1.401(8) . ?
C13 H13A 0.9300 . ?
C17 C16 1.399(8) . ?
C17 H17A 0.9300 . ?
C10 H10A 0.9300 . ?
C5 C4 1.369(8) . ?
C4 C3 1.401(8) . ?
C4 H4A 0.9300 . ?
C3 H3B 0.9300 . ?
C7 H7A 0.9300 . ?
C16 C15 1.467(8) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
O2S C2S 1.376(12) . ?
C1S H1SA 0.9600 . ?
C1S H1SB 0.9600 . ?
C1S H1SC 0.9600 . ?
O1 C1 1.298(7) . ?
O1 Co1 1.999(5) 2_646 ?
O2 C1 1.239(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Co1 N1 143.5(2) 2_656 . ?
O1 Co1 O1S 107.6(2) 2_656 . ?
N1 Co1 O1S 106.42(19) . . ?
O1 Co1 O5 90.93(18) 2_656 . ?
N1 Co1 O5 100.03(18) . . ?
O1S Co1 O5 93.25(17) . . ?
O1 Co1 O6 87.04(17) 2_656 . ?
N1 Co1 O6 82.28(16) . . ?
O1S Co1 O6 86.27(16) . . ?
O5 Co1 O6 177.67(16) . . ?
C19 O6 Co1 134.1(4) . . ?
C14 O5 Co1 141.7(4) . . ?
N1 C18 C17 112.6(5) . . ?
N1 C18 N3 122.6(5) . . ?
C17 C18 N3 124.8(5) . . ?
C5 O3 C8 121.3(4) . . ?
C19 N3 C18 126.4(5) . . ?
C19 N3 H3A 116.8 . . ?
C18 N3 H3A 116.8 . . ?
N1 N2 C16 110.4(5) . . ?
N1 N2 H2A 124.8 . . ?
C16 N2 H2A 124.8 . . ?
C18 N1 N2 105.4(4) . . ?
C18 N1 Co1 132.1(4) . . ?
N2 N1 Co1 121.8(4) . . ?
C1S O1S Co1 126.0(4) . . ?
C21 C20 C22 120.5(5) . . ?
C21 C20 C19 123.0(5) . . ?
C22 C20 C19 116.5(5) . . ?
C8 C9 C10 119.5(6) . . ?
C8 C9 H9A 120.2 . . ?
C10 C9 H9A 120.2 . . ?
C10 C11 C12 118.7(5) . . ?
C10 C11 C14 121.3(5) . . ?
C12 C11 C14 120.1(5) . . ?
C13 C12 C11 119.2(5) . . ?
C13 C12 H12A 120.4 . . ?
C11 C12 H12A 120.4 . . ?
O6 C19 N3 121.9(5) . . ?
O6 C19 C20 120.2(5) . . ?
N3 C19 C20 117.8(5) . . ?
C20 C22 C21 120.2(5) . 3_586 ?
C20 C22 H22A 119.9 . . ?
C21 C22 H22A 119.9 3_586 . ?
C3 C2 C7 119.6(5) . . ?
C3 C2 C1 120.7(5) . . ?
C7 C2 C1 119.7(5) . . ?
C7 C6 C5 119.2(5) . . ?
C7 C6 H6A 120.4 . . ?
C5 C6 H6A 120.4 . . ?
C20 C21 C22 119.3(5) . 3_586 ?
C12 C13 C8 120.3(5) . . ?
C12 C13 H13A 119.9 . . ?
C8 C13 H13A 119.9 . . ?
C18 C17 C16 104.9(5) . . ?
C18 C17 H17A 127.6 . . ?
C16 C17 H17A 127.6 . . ?
C11 C10 C9 122.0(5) . . ?
C11 C10 H10A 119.0 . . ?
C9 C10 H10A 119.0 . . ?
O5 C14 O4 124.4(5) . . ?
O5 C14 C11 117.7(5) . . ?
O4 C14 C11 117.9(4) . . ?
C4 C5 C6 122.7(5) . . ?
C4 C5 O3 122.4(5) . . ?
C6 C5 O3 114.9(5) . . ?
C5 C4 C3 117.8(5) . . ?
C5 C4 H4A 121.1 . . ?
C3 C4 H4A 121.1 . . ?
C2 C3 C4 120.8(5) . . ?
C2 C3 H3B 119.6 . . ?
C4 C3 H3B 119.6 . . ?
C6 C7 C2 119.9(5) . . ?
C6 C7 H7A 120.0 . . ?
C2 C7 H7A 120.0 . . ?
C9 C8 O3 126.0(5) . . ?
C9 C8 C13 120.3(5) . . ?
O3 C8 C13 113.5(5) . . ?
N2 C16 C17 106.7(5) . . ?
N2 C16 C15 121.2(5) . . ?
C17 C16 C15 131.9(5) . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C16 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O1S C1S H1SA 109.5 . . ?
O1S C1S H1SB 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
O1S C1S H1SC 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
C1 O1 Co1 112.1(4) . 2_646 ?
O2 C1 O1 123.3(5) . . ?
O2 C1 C2 119.6(5) . . ?
O1 C1 C2 117.0(5) . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         1.502
_refine_diff_density_min         -2.484
_refine_diff_density_rms         0.251
####################################################################### 
# 
# 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_13SBJ003_0M
_database_code_depnum_ccdc_archive 'CCDC 1434964'
_audit_update_record             
;
2015-11-03 deposited with the CCDC.
2016-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H22 Co N6 O7'
_chemical_formula_weight         565.40

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'

_space_group_crystal_system      hexagonal
_space_group_IT_number           178
_space_group_name_H-M_alt        'P 61 2 2'
_space_group_name_Hall           'P 61 2 (0 0 -1)'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'-x, -y, z+1/2'
'y, -x+y, z+5/6'
'x-y, x, z+1/6'
'y, x, -z+1/3'
'x-y, -y, -z'
'-x, -x+y, -z+2/3'
'-y, -x, -z+5/6'
'-x+y, y, -z+1/2'
'x, x-y, -z+1/6'

_cell_length_a                   8.4490(5)
_cell_length_b                   8.4490(5)
_cell_length_c                   57.241(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3538.7(5)
_cell_formula_units_Z            6
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1549
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      29.10

_exptl_crystal_description       Prism
_exptl_crystal_colour            Purple
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_F_000             1746
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.788
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7255
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
'SADABS v.2.03 (Bruker, 2001), wR2(int)=0.1164 before correction'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-2 CCD area detector'
_diffrn_measurement_method       '/w scans'
_diffrn_detector_area_resol_mean 8
_diffrn_reflns_number            26761
_diffrn_reflns_av_unetI/netI     0.1089
_diffrn_reflns_av_R_equivalents  0.1695
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -76
_diffrn_reflns_limit_l_max       72
_diffrn_reflns_theta_min         2.135
_diffrn_reflns_theta_max         29.112
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             2730
_reflns_number_gt                1912
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.499
_reflns_Friedel_fraction_max     0.806
_reflns_Friedel_fraction_full    0.990

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX-2'
_computing_cell_refinement       'Bruker APEX-2'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0721P)²+3.7546P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 556 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.06(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2730
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1036
_refine_ls_R_factor_gt           0.0658
_refine_ls_wR_factor_ref         0.1729
_refine_ls_wR_factor_gt          0.1483
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.111
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.46009(13) 0.0000 0.0000 0.0197(3) Uani 1 2 d S T P . .
O1W O -0.0210(8) -0.5105(4) 0.0833 0.0201(12) Uani 1 2 d S T P . .
O4 O 0.6213(6) -0.0331(5) 0.02613(6) 0.0256(9) Uani 1 1 d . . . . .
O1 O 0.2170(6) -0.2667(6) 0.05040(7) 0.0296(10) Uani 1 1 d . . . . .
N1 N 0.6296(7) 0.2650(7) 0.00877(8) 0.0248(11) Uani 1 1 d . . . . .
O2 O 0.2712(6) -0.0425(6) 0.02562(6) 0.0294(10) Uani 1 1 d . . . . .
N2 N 0.6574(7) 0.4077(6) -0.00496(8) 0.0232(11) Uani 1 1 d . . . . .
H2A H 0.6076 0.3957 -0.0184 0.028 Uiso 1 1 calc R U . . .
C5 C 0.6883(7) 0.0552(8) 0.04421(9) 0.0209(12) Uani 1 1 d . . . . .
N3 N 0.7405(6) 0.2342(6) 0.04589(8) 0.0231(12) Uani 1 1 d . . . . .
H3A H 0.7834 0.2872 0.0591 0.028 Uiso 1 1 calc R U . . .
C3 C 0.8216(8) 0.5305(8) 0.02646(9) 0.0221(12) Uani 1 1 d . . . . .
H3B H 0.8991 0.6134 0.0376 0.026 Uiso 1 1 calc R U . . .
C4 C 0.7301(8) 0.3405(8) 0.02770(9) 0.0206(12) Uani 1 1 d . . . . .
C2 C 0.7713(8) 0.5692(8) 0.00487(10) 0.0232(13) Uani 1 1 d . . . . .
C10 C 0.2584(8) 0.0170(8) 0.06533(9) 0.0248(13) Uani 1 1 d . . . . .
C6 C 0.7121(8) -0.0373(7) 0.06486(9) 0.0208(12) Uani 1 1 d . . . . .
C7 C 0.7127(9) 0.0166(8) 0.08750(10) 0.0312(15) Uani 1 1 d . . . . .
H7A H 0.7157 0.1263 0.0905 0.047 Uiso 1 1 calc R U . . .
C1 C 0.8224(9) 0.7491(8) -0.00597(10) 0.0263(13) Uani 1 1 d . . . . .
H1A H 0.7937 0.7325 -0.0223 0.039 Uiso 1 1 calc R U . . .
H1B H 0.9511 0.8312 -0.0040 0.039 Uiso 1 1 calc R U . . .
H1C H 0.7554 0.7994 0.0014 0.039 Uiso 1 1 calc R U . . .
C9 C 0.2484(8) -0.1087(9) 0.04567(10) 0.0267(14) Uani 1 1 d . . . . .
C12 C 0.2635(9) -0.0288(8) 0.08862(10) 0.0306(14) Uani 1 1 d . . . . .
H12A H 0.2641 -0.1358 0.0923 0.046 Uiso 1 1 calc R U . . .
C8 C 0.7088(10) -0.1995(9) 0.06070(10) 0.0354(16) Uani 1 1 d . . . . .
H8A H 0.7040 -0.2393 0.0454 0.053 Uiso 1 1 calc R U . . .
C11 C 0.2678(10) 0.1828(10) 0.06049(10) 0.0349(15) Uani 1 1 d . . . . .
H11A H 0.2771 0.2207 0.0450 0.052 Uiso 1 1 calc R U . . .
H1WA H 0.032(9) -0.447(10) 0.0746(13) 0.042 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N1 2.027(5) . ?
Co1 N1 2.027(5) 8 ?
Co1 O2 2.063(4) . ?
Co1 O2 2.063(4) 8 ?
Co1 O4 2.133(4) 8 ?
Co1 O4 2.133(4) . ?
O1W H1WA 0.71(7) . ?
O4 C5 1.236(6) . ?
O1 C9 1.254(8) . ?
N1 C4 1.327(7) . ?
N1 N2 1.358(6) . ?
O2 C9 1.249(7) . ?
N2 C2 1.338(7) . ?
N2 H2A 0.8600 . ?
C5 N3 1.351(7) . ?
C5 C6 1.485(7) . ?
N3 C4 1.406(7) . ?
N3 H3A 0.8600 . ?
C3 C4 1.392(8) . ?
C3 C2 1.398(8) . ?
C3 H3B 0.9300 . ?
C2 C1 1.491(8) . ?
C10 C11 1.391(9) . ?
C10 C12 1.395(8) . ?
C10 C9 1.520(8) . ?
C6 C7 1.373(8) . ?
C6 C8 1.377(8) . ?
C7 C8 1.388(8) 12_545 ?
C7 H7A 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C12 C11 1.379(9) 12 ?
C12 H12A 0.9300 . ?
C8 C7 1.388(8) 12_545 ?
C8 H8A 0.9300 . ?
C11 C12 1.379(9) 12 ?
C11 H11A 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
N1 Co1 N1 162.2(3) . 8 ?
N1 Co1 O2 94.24(18) . . ?
N1 Co1 O2 97.94(17) 8 . ?
N1 Co1 O2 97.94(17) . 8 ?
N1 Co1 O2 94.24(18) 8 8 ?
O2 Co1 O2 93.2(2) . 8 ?
N1 Co1 O4 87.51(17) . 8 ?
N1 Co1 O4 79.99(17) 8 8 ?
O2 Co1 O4 177.59(17) . 8 ?
O2 Co1 O4 88.17(16) 8 8 ?
N1 Co1 O4 79.99(17) . . ?
N1 Co1 O4 87.51(17) 8 . ?
O2 Co1 O4 88.16(16) . . ?
O2 Co1 O4 177.59(17) 8 . ?
O4 Co1 O4 90.5(2) 8 . ?
C5 O4 Co1 129.7(4) . . ?
C4 N1 N2 105.1(5) . . ?
C4 N1 Co1 131.5(4) . . ?
N2 N1 Co1 123.4(3) . . ?
C9 O2 Co1 131.6(4) . . ?
C2 N2 N1 112.3(4) . . ?
C2 N2 H2A 123.9 . . ?
N1 N2 H2A 123.9 . . ?
O4 C5 N3 122.0(5) . . ?
O4 C5 C6 119.4(5) . . ?
N3 C5 C6 118.6(5) . . ?
C5 N3 C4 124.9(5) . . ?
C5 N3 H3A 117.5 . . ?
C4 N3 H3A 117.5 . . ?
C4 C3 C2 104.9(5) . . ?
C4 C3 H3B 127.6 . . ?
C2 C3 H3B 127.6 . . ?
N1 C4 C3 111.4(5) . . ?
N1 C4 N3 121.8(5) . . ?
C3 C4 N3 126.7(5) . . ?
N2 C2 C3 106.3(5) . . ?
N2 C2 C1 124.0(5) . . ?
C3 C2 C1 129.7(5) . . ?
C11 C10 C12 118.4(5) . . ?
C11 C10 C9 120.8(5) . . ?
C12 C10 C9 120.8(6) . . ?
C7 C6 C8 119.2(5) . . ?
C7 C6 C5 123.7(5) . . ?
C8 C6 C5 116.5(5) . . ?
C6 C7 C8 120.3(5) . 12_545 ?
C6 C7 H7A 119.8 . . ?
C8 C7 H7A 119.8 12_545 . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C9 O1 125.4(6) . . ?
O2 C9 C10 115.1(5) . . ?
O1 C9 C10 119.5(5) . . ?
C11 C12 C10 119.8(6) 12 . ?
C11 C12 H12A 120.1 12 . ?
C10 C12 H12A 120.1 . . ?
C6 C8 C7 120.4(5) . 12_545 ?
C6 C8 H8A 119.8 . . ?
C7 C8 H8A 119.8 12_545 . ?
C12 C11 C10 121.5(5) 12 . ?
C12 C11 H11A 119.2 12 . ?
C10 C11 H11A 119.2 . . ?

_refine_diff_density_max         0.619
_refine_diff_density_min         -0.854
_refine_diff_density_rms         0.148

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_sbj14713
_database_code_depnum_ccdc_archive 'CCDC 1434965'
_audit_update_record             
;
2015-11-03 deposited with the CCDC.
2016-02-19 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 H14 Co F6 N3 O5'
_chemical_formula_weight         609.32

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'
F F 0.0171 0.0103 '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                   26.393(4)
_cell_length_b                   11.0092(15)
_cell_length_c                   24.857(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 118.483(4)
_cell_angle_gamma                90.00
_cell_volume                     6348.4(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       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2448
_exptl_absorpt_coefficient_mu    0.609
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            31076
_diffrn_reflns_av_R_equivalents  0.0770
_diffrn_reflns_av_sigmaI/netI    0.0504
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         23.28
_reflns_number_total             4551
_reflns_number_gt                2858
_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)+(0.1000P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4551
_refine_ls_number_parameters     424
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1658
_refine_ls_R_factor_gt           0.1006
_refine_ls_wR_factor_ref         0.3034
_refine_ls_wR_factor_gt          0.2650
_refine_ls_goodness_of_fit_ref   1.945
_refine_ls_restrained_S_all      1.945
_refine_ls_shift/su_max          0.040
_refine_ls_shift/su_mean         0.005

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 0.27874(4) 1.13572(9) 0.01549(5) 0.0532(5) Uani 1 1 d . . .
O1 O 0.2183(3) 1.1190(5) 0.0439(3) 0.0709(18) Uani 1 1 d . . .
C2 C 0.1448(4) 1.1501(8) 0.0703(4) 0.061(2) Uani 1 1 d . . .
C11 C 0.0738(4) 0.9522(8) 0.2083(4) 0.062(2) Uani 1 1 d . . .
C5 C 0.0746(4) 1.0653(8) 0.1185(4) 0.062(2) Uani 1 1 d . . .
C8 C 0.0367(4) 1.0173(9) 0.1446(4) 0.069(3) Uani 1 1 d . . .
C1 C 0.1814(4) 1.1898(9) 0.0435(5) 0.070(3) Uani 1 1 d . . .
C3 C 0.1537(4) 1.0362(9) 0.0976(5) 0.085(3) Uani 1 1 d . . .
H3A H 0.1829 0.9858 0.0996 0.102 Uiso 1 1 calc R . .
C12 C 0.0585(4) 0.8469(9) 0.2260(5) 0.072(3) Uani 1 1 d . . .
H12A H 0.0251 0.8064 0.1990 0.086 Uiso 1 1 calc R . .
C7 C 0.0990(4) 1.2190(8) 0.0661(4) 0.068(3) Uani 1 1 d . . .
H7A H 0.0916 1.2940 0.0466 0.082 Uiso 1 1 calc R . .
C16 C 0.1216(4) 1.0137(8) 0.2507(4) 0.079(3) Uani 1 1 d . . .
H16A H 0.1315 1.0873 0.2399 0.094 Uiso 1 1 calc R . .
C4 C 0.1192(4) 0.9995(8) 0.1215(5) 0.081(3) Uani 1 1 d . . .
H4A H 0.1267 0.9245 0.1410 0.097 Uiso 1 1 calc R . .
C9 C 0.0010(5) 1.1145(14) 0.1571(5) 0.092(4) Uani 1 1 d . . .
C6 C 0.0646(4) 1.1800(9) 0.0897(4) 0.067(3) Uani 1 1 d . . .
H6A H 0.0347 1.2288 0.0868 0.081 Uiso 1 1 calc R . .
C10 C -0.0028(6) 0.9205(18) 0.0961(6) 0.111(5) Uani 1 1 d . . .
O2 O 0.1722(3) 1.2951(6) 0.0198(3) 0.085(2) Uani 1 1 d . . .
C15 C 0.1544(4) 0.9696(9) 0.3075(5) 0.088(3) Uani 1 1 d . . .
H15A H 0.1864 1.0132 0.3352 0.105 Uiso 1 1 calc R . .
C14 C 0.1410(4) 0.8593(8) 0.3252(4) 0.065(2) Uani 1 1 d . . .
C17 C 0.1776(4) 0.8129(9) 0.3888(5) 0.071(3) Uani 1 1 d . . .
C13 C 0.0926(4) 0.8007(8) 0.2836(5) 0.066(3) Uani 1 1 d . . .
H13A H 0.0824 0.7275 0.2945 0.079 Uiso 1 1 calc R . .
O5 O 0.2153(3) 0.8813(6) 0.4266(3) 0.0767(19) Uani 1 1 d . . .
O4 O 0.1687(3) 0.7048(6) 0.4001(3) 0.092(2) Uani 1 1 d . . .
C25 C 0.3069(10) 0.9341(18) -0.2641(11) 0.088(7) Uani 0.50 1 d P A 1
C24 C 0.3057(11) 0.8771(18) -0.2197(11) 0.081(7) Uani 0.50 1 d P A 1
H24A H 0.3040 0.7927 -0.2201 0.097 Uiso 0.50 1 calc PR A 1
C23 C 0.3068(7) 0.9394(17) -0.1722(11) 0.068(6) Uani 0.50 1 d P A 1
C22 C 0.3101(7) 0.8801(18) -0.1200(9) 0.060(5) Uani 0.50 1 d P A 1
O3 O 0.3109(9) 0.7585(12) -0.1187(9) 0.135(7) Uani 0.50 1 d P A 1
N3 N 0.3128(6) 0.9378(14) -0.0760(9) 0.110(8) Uani 0.50 1 d P A 1
H3B H 0.3154 1.0152 -0.0785 0.132 Uiso 0.50 1 calc PR A 1
C18 C 0.3353(9) 0.6795(17) 0.1074(10) 0.087(7) Uani 0.50 1 d P B 1
H18A H 0.3449 0.6059 0.0936 0.131 Uiso 0.50 1 calc PR B 1
H18B H 0.3006 0.6675 0.1103 0.131 Uiso 0.50 1 calc PR B 1
H18C H 0.3662 0.7011 0.1468 0.131 Uiso 0.50 1 calc PR B 1
C25' C 0.3031(8) 0.9398(18) 0.3219(11) 0.079(6) Uani 0.50 1 d P C 2
C24' C 0.2991(9) 0.8787(15) 0.2722(9) 0.066(5) Uani 0.50 1 d P C 2
H24B H 0.2929 0.7952 0.2678 0.080 Uiso 0.50 1 calc PR C 2
C23' C 0.3045(8) 0.9451(18) 0.2302(9) 0.073(6) Uani 0.50 1 d P C 2
C22' C 0.3076(7) 0.8827(19) 0.1777(8) 0.065(5) Uani 0.50 1 d P C 2
O3' O 0.3053(9) 0.7612(12) 0.1763(7) 0.133(7) Uani 0.50 1 d P C 2
N3' N 0.3136(7) 0.9406(17) 0.1400(11) 0.107(8) Uani 0.50 1 d P C 2
H3'A H 0.3191 1.0173 0.1468 0.128 Uiso 0.50 1 calc PR C 2
C18' C 0.3347(8) 0.6780(16) -0.0191(9) 0.078(6) Uani 0.50 1 d P D 2
H18D H 0.3443 0.6054 0.0051 0.116 Uiso 0.50 1 calc PR D 2
H18E H 0.3654 0.6979 -0.0278 0.116 Uiso 0.50 1 calc PR D 2
H18F H 0.2998 0.6652 -0.0568 0.116 Uiso 0.50 1 calc PR D 2
N2 N 0.3053(3) 0.9627(7) 0.0273(4) 0.077(3) Uani 1 1 d . A .
C20 C 0.3270(4) 0.7697(8) 0.0118(6) 0.082(3) Uani 1 1 d . . .
C19 C 0.3269(4) 0.7700(9) 0.0669(6) 0.081(3) Uani 1 1 d . B .
N1 N 0.3127(4) 0.8884(8) 0.0730(5) 0.091(3) Uani 1 1 d . . .
C21 C 0.3123(4) 0.8876(7) -0.0097(5) 0.064(3) Uani 1 1 d . A .
F1 F -0.0301(3) 0.9824(9) 0.0393(3) 0.136(3) Uani 1 1 d . . .
F2 F -0.0477(3) 0.8879(8) 0.1059(3) 0.129(3) Uani 1 1 d . . .
F3 F 0.0233(4) 0.8285(8) 0.0920(4) 0.121(3) Uani 1 1 d . . .
F4 F -0.0260(3) 1.0677(8) 0.1852(3) 0.130(3) Uani 1 1 d . . .
F5 F 0.0341(4) 1.2043(7) 0.1899(3) 0.113(2) Uani 1 1 d . . .
F6 F -0.0391(3) 1.1665(8) 0.1041(3) 0.127(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 N2 2.002(8) . ?
Co1 O2 2.028(6) 7_575 ?
Co1 O4 2.033(7) 4 ?
Co1 O1 2.037(6) . ?
Co1 O5 2.048(6) 6_575 ?
Co1 Co1 2.848(2) 7_575 ?
O1 C1 1.246(11) . ?
C2 C7 1.388(12) . ?
C2 C3 1.391(12) . ?
C2 C1 1.476(13) . ?
C11 C12 1.366(12) . ?
C11 C16 1.377(12) . ?
C11 C8 1.582(12) . ?
C5 C4 1.354(12) . ?
C5 C6 1.413(12) . ?
C5 C8 1.521(12) . ?
C8 C9 1.552(15) . ?
C8 C10 1.573(17) . ?
C1 O2 1.270(10) . ?
C3 C4 1.365(13) . ?
C3 H3A 0.9300 . ?
C12 C13 1.375(12) . ?
C12 H12A 0.9300 . ?
C7 C6 1.363(12) . ?
C7 H7A 0.9300 . ?
C16 C15 1.346(13) . ?
C16 H16A 0.9300 . ?
C4 H4A 0.9300 . ?
C9 F5 1.313(14) . ?
C9 F4 1.320(12) . ?
C9 F6 1.361(11) . ?
C6 H6A 0.9300 . ?
C10 F3 1.256(18) . ?
C10 F2 1.367(13) . ?
C10 F1 1.416(15) . ?
O2 Co1 2.028(6) 7_575 ?
C15 C14 1.393(12) . ?
C15 H15A 0.9300 . ?
C14 C13 1.363(12) . ?
C14 C17 1.497(13) . ?
C17 O5 1.243(11) . ?
C17 O4 1.270(11) . ?
C13 H13A 0.9300 . ?
O5 Co1 2.048(6) 6_576 ?
O4 Co1 2.033(7) 4_545 ?
C25 C24 1.28(3) . ?
C24 C23 1.35(2) . ?
C24 H24A 0.9300 . ?
C23 C22 1.42(3) . ?
C22 N3 1.24(2) . ?
C22 O3 1.34(2) . ?
N3 C21 1.74(3) . ?
N3 H3B 0.8600 . ?
C18 C19 1.36(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C25' C24' 1.37(3) . ?
C24' C23' 1.34(2) . ?
C24' H24B 0.9300 . ?
C23' C22' 1.51(3) . ?
C22' N3' 1.21(2) . ?
C22' O3' 1.34(2) . ?
N3' N1 1.75(2) . ?
N3' H3'A 0.8600 . ?
C18' C20 1.342(19) . ?
C18' H18D 0.9600 . ?
C18' H18E 0.9600 . ?
C18' H18F 0.9600 . ?
N2 C21 1.313(12) . ?
N2 N1 1.336(12) . ?
C20 C19 1.372(16) . ?
C20 C21 1.386(12) . ?
C19 N1 1.384(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Co1 O2 99.8(3) . 7_575 ?
N2 Co1 O4 100.7(3) . 4 ?
O2 Co1 O4 92.5(3) 7_575 4 ?
N2 Co1 O1 98.0(3) . . ?
O2 Co1 O1 162.0(2) 7_575 . ?
O4 Co1 O1 86.4(3) 4 . ?
N2 Co1 O5 96.9(3) . 6_575 ?
O2 Co1 O5 85.9(3) 7_575 6_575 ?
O4 Co1 O5 162.3(3) 4 6_575 ?
O1 Co1 O5 89.7(3) . 6_575 ?
N2 Co1 Co1 169.8(2) . 7_575 ?
O2 Co1 Co1 85.34(19) 7_575 7_575 ?
O4 Co1 Co1 87.8(2) 4 7_575 ?
O1 Co1 Co1 76.69(17) . 7_575 ?
O5 Co1 Co1 74.52(19) 6_575 7_575 ?
C1 O1 Co1 132.9(6) . . ?
C7 C2 C3 117.9(9) . . ?
C7 C2 C1 122.5(8) . . ?
C3 C2 C1 119.4(9) . . ?
C12 C11 C16 118.3(8) . . ?
C12 C11 C8 124.8(8) . . ?
C16 C11 C8 116.6(8) . . ?
C4 C5 C6 116.9(8) . . ?
C4 C5 C8 121.4(8) . . ?
C6 C5 C8 121.6(8) . . ?
C5 C8 C9 115.5(9) . . ?
C5 C8 C10 103.8(8) . . ?
C9 C8 C10 112.1(10) . . ?
C5 C8 C11 111.5(7) . . ?
C9 C8 C11 104.8(7) . . ?
C10 C8 C11 109.1(9) . . ?
O1 C1 O2 123.3(10) . . ?
O1 C1 C2 119.3(8) . . ?
O2 C1 C2 117.3(9) . . ?
C4 C3 C2 119.1(9) . . ?
C4 C3 H3A 120.5 . . ?
C2 C3 H3A 120.5 . . ?
C11 C12 C13 120.2(8) . . ?
C11 C12 H12A 119.9 . . ?
C13 C12 H12A 119.9 . . ?
C6 C7 C2 122.0(9) . . ?
C6 C7 H7A 119.0 . . ?
C2 C7 H7A 119.0 . . ?
C15 C16 C11 121.5(9) . . ?
C15 C16 H16A 119.3 . . ?
C11 C16 H16A 119.3 . . ?
C5 C4 C3 124.2(9) . . ?
C5 C4 H4A 117.9 . . ?
C3 C4 H4A 117.9 . . ?
F5 C9 F4 109.3(11) . . ?
F5 C9 F6 105.3(11) . . ?
F4 C9 F6 107.9(9) . . ?
F5 C9 C8 110.9(9) . . ?
F4 C9 C8 111.8(11) . . ?
F6 C9 C8 111.3(10) . . ?
C7 C6 C5 119.9(9) . . ?
C7 C6 H6A 120.1 . . ?
C5 C6 H6A 120.1 . . ?
F3 C10 F2 110.9(14) . . ?
F3 C10 F1 110.1(12) . . ?
F2 C10 F1 103.4(10) . . ?
F3 C10 C8 114.9(11) . . ?
F2 C10 C8 110.9(11) . . ?
F1 C10 C8 105.9(12) . . ?
C1 O2 Co1 121.6(7) . 7_575 ?
C16 C15 C14 120.8(9) . . ?
C16 C15 H15A 119.6 . . ?
C14 C15 H15A 119.6 . . ?
C13 C14 C15 117.4(9) . . ?
C13 C14 C17 122.6(9) . . ?
C15 C14 C17 119.9(9) . . ?
O5 C17 O4 124.5(9) . . ?
O5 C17 C14 118.2(9) . . ?
O4 C17 C14 117.3(10) . . ?
C14 C13 C12 121.7(9) . . ?
C14 C13 H13A 119.2 . . ?
C12 C13 H13A 119.2 . . ?
C17 O5 Co1 135.0(6) . 6_576 ?
C17 O4 Co1 118.1(7) . 4_545 ?
C25 C24 C23 120.2(19) . . ?
C25 C24 H24A 119.9 . . ?
C23 C24 H24A 119.9 . . ?
C24 C23 C22 122.1(18) . . ?
N3 C22 O3 120(2) . . ?
N3 C22 C23 122(2) . . ?
O3 C22 C23 118.3(17) . . ?
C22 N3 C21 130.5(16) . . ?
C22 N3 H3B 114.7 . . ?
C21 N3 H3B 114.8 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C19 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C23' C24' C25' 116.5(17) . . ?
C23' C24' H24B 121.8 . . ?
C25' C24' H24B 121.8 . . ?
C24' C23' C22' 119.7(18) . . ?
N3' C22' O3' 122(2) . . ?
N3' C22' C23' 121(2) . . ?
O3' C22' C23' 117.2(18) . . ?
C22' N3' N1 128.3(19) . . ?
C22' N3' H3'A 115.9 . . ?
N1 N3' H3'A 115.8 . . ?
C20 C18' H18D 109.5 . . ?
C20 C18' H18E 109.5 . . ?
H18D C18' H18E 109.5 . . ?
C20 C18' H18F 109.5 . . ?
H18D C18' H18F 109.5 . . ?
H18E C18' H18F 109.5 . . ?
C21 N2 N1 101.4(8) . . ?
C21 N2 Co1 130.7(7) . . ?
N1 N2 Co1 127.3(8) . . ?
C18' C20 C19 130.3(13) . . ?
C18' C20 C21 125.1(15) . . ?
C19 C20 C21 104.4(10) . . ?
C18 C19 C20 131.4(13) . . ?
C18 C19 N1 124.6(15) . . ?
C20 C19 N1 103.9(10) . . ?
N2 N1 C19 114.9(11) . . ?
N2 N1 N3' 122.6(9) . . ?
C19 N1 N3' 122.1(11) . . ?
N2 C21 C20 115.2(11) . . ?
N2 C21 N3 122.0(8) . . ?
C20 C21 N3 122.2(11) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        23.28
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         2.144
_refine_diff_density_min         -0.919
_refine_diff_density_rms         0.321
