# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_1
_database_code_depnum_ccdc_archive 'CCDC 1409462'
_audit_update_record             
;
2015-10-06 deposited with the CCDC.
2015-10-21 downloaded from the CCDC.
;

_audit_creation_date             2015-10-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         
'0.11(C144 H227.21 Co27 N36 O126), 2(H O), H2 O'
_chemical_formula_sum            'C16 H29.25 Co3 N4 O17'
_chemical_formula_weight         726.47
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           167
_space_group_name_H-M_alt        'R -3 c'
_space_group_name_Hall           '-R 3 2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'y, x, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'y+2/3, x+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'y+1/3, x+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-y, -x, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-y+2/3, -x+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'
'-y+1/3, -x+2/3, z+1/6'

_cell_length_a                   24.4314(6)
_cell_length_b                   24.4314(6)
_cell_length_c                   27.9400(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     14442.9(9)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    4193
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1275
_cell_measurement_theta_min      2.7446
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.603
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99436
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             6664
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11498
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         2.750
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0710
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   37.00   85.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -       18.1148  178.0000   30.0000 48

#__ type_ start__ end____ width___ exp.time_
  2 omega    2.00   73.00   1.0000  180.0000
omega____ theta____ kappa____ phi______ frames
    -       18.1148   38.0000 -180.0000 71
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0221801000
_diffrn_orient_matrix_UB_12      0.0010243000
_diffrn_orient_matrix_UB_13      0.0168736000
_diffrn_orient_matrix_UB_21      -0.0138286000
_diffrn_orient_matrix_UB_22      -0.0332970000
_diffrn_orient_matrix_UB_23      -0.0016132000
_diffrn_orient_matrix_UB_31      0.0210071000
_diffrn_orient_matrix_UB_32      0.0037356000
_diffrn_orient_matrix_UB_33      -0.0188825000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2735
_reflns_number_total             3288
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.607
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3288
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0319
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0572P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0912
_refine_ls_wR_factor_ref         0.0948
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Rigid bond restraints
 Co1, O2W
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3. Uiso/Uaniso restraints and constraints
Uanis(C8) = Uanis(C8A)
4. Others
 Sof(H6BC)=Sof(H6BD)=Sof(C7A)=Sof(H7AA)=1-FVAR(1)
 Sof(H6AA)=Sof(H6AB)=Sof(C7)=Sof(H7A)=Sof(H7B)=FVAR(1)
 Fixed Sof: C8(0.5) H8A(0.5) H8B(0.5) H8C(0.5) C8A(0.5) H8AA(0.5) H8AB(0.5)
 H8AC(0.5)
5.a Rotating group:
 O1W(H1WA,H1WB), O2W(H2WA,H2WB), O3W(H3WA)
5.b Secondary CH2 refined with riding coordinates:
 C6(H6AA,H6AB), C6(H6BC,H6BD), C7(H7A,H7B)
5.c Aromatic/amide H refined with riding coordinates:
 C7A(H7AA)
5.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C8A(H8AA,H8AB,H8AC)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.58485(2) 0.65556(2) 0.66817(2) 0.01739(12) Uani 1 1 d . U . . .
Co2 Co 0.5000 0.5000 0.5000 0.02499(14) Uani 1 2 d S T P . .
O1 O 0.58134(7) 0.64538(7) 0.59180(5) 0.0226(4) Uani 1 1 d . . . . .
O1W O 0.68680(8) 0.70956(9) 0.66216(6) 0.0355(4) Uani 1 1 d . . . . .
H1WA H 0.7046 0.7133 0.6353 0.053 Uiso 1 1 d GR . . . .
H1WB H 0.7112 0.6991 0.6794 0.053 Uiso 1 1 d GR . . . .
O2 O 0.52304(8) 0.58325(8) 0.53274(5) 0.0310(4) Uani 1 1 d . . . . .
O2W O 0.60383(8) 0.57748(8) 0.67534(6) 0.0331(4) Uani 1 1 d . U . . .
H2WA H 0.5686 0.5413 0.6751 0.050 Uiso 1 1 d GR . . . .
H2WB H 0.6234 0.5804 0.7022 0.050 Uiso 1 1 d GR . . . .
O3 O 0.41476(8) 0.45036(9) 0.53646(6) 0.0345(5) Uani 1 1 d . . . . .
O3W O 0.45125(9) 0.52279(10) 0.44664(7) 0.0422(5) Uani 1 1 d . . . . .
H3WA H 0.4142 0.4905 0.4406 0.063 Uiso 1 1 d GR . . . .
O4 O 0.33851(7) 0.40763(7) 0.58992(6) 0.0230(4) Uani 1 1 d . . . . .
N1 N 0.49277(9) 0.58376(9) 0.65791(6) 0.0191(4) Uani 1 1 d . . . . .
N2 N 0.40317(8) 0.49092(9) 0.65796(6) 0.0192(4) Uani 1 1 d . . . . .
C1 C 0.42793(10) 0.50190(11) 0.61220(7) 0.0181(5) Uani 1 1 d . . . . .
C2 C 0.48351(10) 0.55975(11) 0.61255(7) 0.0185(5) Uani 1 1 d . . . . .
C3 C 0.44369(10) 0.54129(11) 0.68382(8) 0.0210(5) Uani 1 1 d . . . . .
C4 C 0.39289(10) 0.45144(11) 0.57670(7) 0.0196(5) Uani 1 1 d . . . . .
C5 C 0.53179(10) 0.59743(11) 0.57646(7) 0.0195(5) Uani 1 1 d . . . . .
C6 C 0.43494(14) 0.55001(14) 0.73565(9) 0.0419(8) Uani 1 1 d . . . . .
H6AA H 0.4720 0.5568 0.7533 0.050 Uiso 0.623(17) 1 calc R . . A 1
H6AB H 0.3988 0.5118 0.7478 0.050 Uiso 0.623(17) 1 calc R . . A 1
H6BC H 0.4749 0.5821 0.7489 0.050 Uiso 0.377(17) 1 calc R . . A 2
H6BD H 0.4224 0.5108 0.7525 0.050 Uiso 0.377(17) 1 calc R . . A 2
C7 C 0.4245(7) 0.6061(6) 0.7440(3) 0.096(4) Uani 0.623(17) 1 d . . . A 1
H7A H 0.4308 0.6181 0.7775 0.115 Uiso 0.623(17) 1 calc R . . A 1
H7B H 0.4543 0.6421 0.7251 0.115 Uiso 0.623(17) 1 calc R . . A 1
C7A C 0.3861(6) 0.5691(7) 0.7436(3) 0.048(4) Uani 0.377(17) 1 d . . . A 2
H7AA H 0.3462 0.5426 0.7564 0.057 Uiso 0.377(17) 1 calc R . . A 2
C8 C 0.3678(7) 0.5891(8) 0.7315(8) 0.156(6) Uani 0.5 1 d . . . A 1
H8A H 0.3443 0.5440 0.7278 0.235 Uiso 0.5 1 calc GR . . A 1
H8B H 0.3684 0.6088 0.7016 0.235 Uiso 0.5 1 calc GR . . A 1
H8C H 0.3483 0.6016 0.7556 0.235 Uiso 0.5 1 calc GR . . A 1
C8A C 0.4091(8) 0.6365(6) 0.7285(7) 0.156(6) Uani 0.5 1 d . . . A 2
H8AA H 0.4313 0.6645 0.7545 0.235 Uiso 0.5 1 calc GR . . A 2
H8AB H 0.3736 0.6411 0.7197 0.235 Uiso 0.5 1 calc GR . . A 2
H8AC H 0.4370 0.6468 0.7016 0.235 Uiso 0.5 1 calc GR . . A 2
O4W O 0.48733(13) 0.55748(14) 0.35187(8) 0.0638(7) Uani 1 1 d . . . . .
O6W O 0.3333 0.42267(15) 0.4167 0.0529(8) Uani 1 2 d S T P . .
H3WB H 0.4735(15) 0.5356(15) 0.4165(14) 0.065(11) Uiso 1 1 d . . . . .
H6W H 0.333(3) 0.402(2) 0.3908(17) 0.14(2) Uiso 1 1 d . . . . .
H4W H 0.529(3) 0.574(3) 0.3426(19) 0.15(2) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O1 2.1451(16) . ?
Co1 O1W 2.1650(17) . ?
Co1 O2W 2.1861(17) . ?
Co1 O4 2.1332(16) 27_556 ?
Co1 N1 2.0673(19) . ?
Co1 N2 2.0638(18) 27_556 ?
Co2 O2 2.0361(16) 19_666 ?
Co2 O2 2.0361(16) . ?
Co2 O3 2.0784(16) . ?
Co2 O3 2.0785(16) 19_666 ?
Co2 O3W 2.148(2) 19_666 ?
Co2 O3W 2.148(2) . ?
O1 C5 1.266(3) . ?
O2 C5 1.259(3) . ?
O3 C4 1.251(3) . ?
O4 Co1 2.1332(16) 26_456 ?
O4 C4 1.275(3) . ?
N1 C2 1.367(3) . ?
N1 C3 1.339(3) . ?
N2 Co1 2.0636(18) 26_456 ?
N2 C1 1.382(3) . ?
N2 C3 1.341(3) . ?
C1 C2 1.386(3) . ?
C1 C4 1.477(3) . ?
C2 C5 1.473(3) . ?
C3 C6 1.495(3) . ?
C6 C7 1.532(9) . ?
C6 C7A 1.501(10) . ?
C7 C8 1.280(19) . ?
C7A C8A 1.51(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Co1 O1W 87.74(6) . . ?
O1 Co1 O2W 90.20(6) . . ?
O1W Co1 O2W 81.80(7) . . ?
O4 Co1 O1 174.64(6) 27_556 . ?
O4 Co1 O1W 86.97(7) 27_556 . ?
O4 Co1 O2W 89.89(6) 27_556 . ?
N1 Co1 O1 78.48(6) . . ?
N1 Co1 O1W 159.82(7) . . ?
N1 Co1 O2W 83.57(7) . . ?
N1 Co1 O4 106.86(7) . 27_556 ?
N2 Co1 O1 100.97(7) 27_556 . ?
N2 Co1 O1W 91.97(7) 27_556 . ?
N2 Co1 O2W 167.02(7) 27_556 . ?
N2 Co1 O4 78.37(6) 27_556 27_556 ?
N2 Co1 N1 104.98(8) 27_556 . ?
O2 Co2 O2 180.0 . 19_666 ?
O2 Co2 O3 93.36(7) 19_666 19_666 ?
O2 Co2 O3 86.64(7) 19_666 . ?
O2 Co2 O3 86.65(7) . 19_666 ?
O2 Co2 O3 93.36(7) . . ?
O2 Co2 O3W 88.00(7) . . ?
O2 Co2 O3W 87.99(7) 19_666 19_666 ?
O2 Co2 O3W 92.00(7) . 19_666 ?
O2 Co2 O3W 92.01(7) 19_666 . ?
O3 Co2 O3 180.0 . 19_666 ?
O3 Co2 O3W 91.85(8) 19_666 . ?
O3 Co2 O3W 91.85(8) . 19_666 ?
O3 Co2 O3W 88.15(8) 19_666 19_666 ?
O3 Co2 O3W 88.15(8) . . ?
O3W Co2 O3W 180.0 . 19_666 ?
C5 O1 Co1 114.09(13) . . ?
C5 O2 Co2 129.43(16) . . ?
C4 O3 Co2 137.92(15) . . ?
C4 O4 Co1 114.50(13) . 26_456 ?
C2 N1 Co1 111.66(14) . . ?
C3 N1 Co1 139.04(16) . . ?
C3 N1 C2 106.06(18) . . ?
C1 N2 Co1 113.03(14) . 26_456 ?
C3 N2 Co1 141.20(15) . 26_456 ?
C3 N2 C1 105.64(18) . . ?
N2 C1 C2 107.57(18) . . ?
N2 C1 C4 116.39(19) . . ?
C2 C1 C4 135.98(19) . . ?
N1 C2 C1 108.15(18) . . ?
N1 C2 C5 117.22(19) . . ?
C1 C2 C5 134.62(19) . . ?
N1 C3 N2 112.6(2) . . ?
N1 C3 C6 123.3(2) . . ?
N2 C3 C6 124.1(2) . . ?
O3 C4 O4 121.3(2) . . ?
O3 C4 C1 123.1(2) . . ?
O4 C4 C1 115.59(18) . . ?
O1 C5 C2 116.30(18) . . ?
O2 C5 O1 122.4(2) . . ?
O2 C5 C2 121.3(2) . . ?
C3 C6 C7 112.0(4) . . ?
C3 C6 C7A 112.4(4) . . ?
C8 C7 C6 107.7(11) . . ?
C6 C7A C8A 112.2(10) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.250 525.9 6.7 ?
2 0.000 0.000 0.750 525.9 6.5 ?
3 0.333 0.667 0.417 525.9 6.5 ?
4 0.333 0.667 0.917 525.9 6.7 ?
5 0.667 0.333 0.083 525.9 6.5 ?
6 0.667 0.333 0.583 525.9 6.7 ?
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1409463'
_audit_update_record             
;
2015-10-06 deposited with the CCDC.
2015-10-21 downloaded from the CCDC.
;

_audit_creation_date             2015-10-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H14 Co2 N4 O8'
_chemical_formula_sum            'C16 H14 Co2 N4 O8'
_chemical_formula_weight         508.17
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           55
_space_group_name_H-M_alt        'P b a m'
_space_group_name_Hall           '-P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z'
'x-1/2, -y-1/2, z'
'-x-1/2, y-1/2, z'

_cell_length_a                   15.9765(17)
_cell_length_b                   15.0880(15)
_cell_length_c                   15.9616(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3847.6(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3756
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.700
_cell_measurement_theta_min      2.253
_shelx_estimated_absorpt_T_max   0.815
_shelx_estimated_absorpt_T_min   0.696
_exptl_absorpt_coefficient_mu    1.778
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.702772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
? was used for absorption correction.
R(int) was 0.0490 before and 0.0337 after correction.
The Ratio of minimum to maximum transmission is 0.7028.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.755
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2048
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22442
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.276
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3243
_reflns_number_total             4089
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         1.221
_refine_diff_density_min         -0.964
_refine_diff_density_rms         0.128
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4089
_refine_ls_number_restraints     348
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0568
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0996P)²+7.7106P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1641
_refine_ls_wR_factor_ref         0.1769
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C6' \\sim C7 \\sim C7'
\\sim C8 \\sim C8' \\sim C9 \\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14
\\sim C15 \\sim C16 \\sim C17 \\sim C18 \\sim C19 \\sim C20: within 3.8A with
sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C6) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C6') \\sim
Ueq, Uanis(C7') \\sim Ueq, Uanis(C8') \\sim Ueq: with sigma of 0.1 and sigma
for terminal atoms of 0.2
3. Others
 Sof(C6')=Sof(H6'A)=Sof(H6'B)=Sof(C7')=Sof(H7'A)=Sof(H7'B)=Sof(C8')=Sof(H8'A)=
 Sof(H8'B)=Sof(H8'C)=1-FVAR(1)
 Sof(C6)=Sof(H6A)=Sof(H6B)=Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(C8)=Sof(H8A)=Sof(H8B)=
 Sof(H8C)=FVAR(1)
 Fixed Sof: H12A(0.5) H12B(0.5) H13A(0.5) H13B(0.5) H14B(0.5) H14C(0.5)
 H18A(0.5) H18B(0.5) H19A(0.5) H19B(0.5) H20B(0.5) H20C(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C6'(H6'A,H6'B), C7(H7A,H7B), C7'(H7'A,H7'B), C12(H12A,H12B),
 C13(H13A,H13B), C18(H18A,H18B), C19(H19A,H19B)
4.b Me refined with riding coordinates:
 C8'(H8'A,H8'B,H8'C), C14(H14A,H14B,H14C), C20(H20A,H20B,H20C)
4.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.16712(4) 0.31653(5) 0.29979(4) 0.0322(2) Uani 1 1 d . . . . .
Co2 Co -0.00254(3) 0.38888(4) 0.19956(3) 0.0212(2) Uani 1 1 d . . . . .
O1 O 0.4177(2) -0.00234(19) 0.21031(18) 0.0278(7) Uani 1 1 d . . . . .
O2 O 0.2979(2) -0.0478(2) 0.2690(2) 0.0353(8) Uani 1 1 d . . . . .
O3 O 0.1585(3) 0.0391(3) 0.3140(3) 0.0638(13) Uani 1 1 d . . . . .
O4 O 0.1186(2) 0.1801(3) 0.3207(3) 0.0485(10) Uani 1 1 d . . . . .
O5 O 0.1065(2) 0.3051(2) 0.18027(18) 0.0291(7) Uani 1 1 d . . . . .
O6 O 0.1910(2) 0.2584(3) 0.0791(2) 0.0505(11) Uani 1 1 d . . . . .
O7 O -0.0484(2) 0.4058(3) 0.4215(2) 0.0486(10) Uani 1 1 d . . . . .
O8 O 0.0415(2) 0.3663(2) 0.32177(18) 0.0316(7) Uani 1 1 d . . . . .
N1 N 0.2705(3) 0.2409(3) 0.2717(3) 0.0353(9) Uani 1 1 d . . . . .
N2 N 0.3850(2) 0.1681(2) 0.2304(2) 0.0283(8) Uani 1 1 d . . . . .
N3 N -0.0029(2) 0.3764(2) 0.0701(2) 0.0217(7) Uani 1 1 d . . . . .
N4 N 0.1666(2) 0.3349(3) 0.4297(2) 0.0340(9) Uani 1 1 d . . . . .
C1 C 0.3497(3) 0.2473(3) 0.2450(3) 0.0329(9) Uani 1 1 d . . . . .
C2 C 0.3248(3) 0.1062(3) 0.2500(3) 0.0294(9) Uani 1 1 d . . . . .
C3 C 0.2554(3) 0.1515(3) 0.2757(3) 0.0321(10) Uani 1 1 d . . . . .
C4 C 0.3467(3) 0.0107(3) 0.2431(3) 0.0272(9) Uani 1 1 d . . . . .
C5 C 0.1727(3) 0.1242(4) 0.3052(3) 0.0374(11) Uani 1 1 d . . . . .
C6 C 0.3999(16) 0.3322(18) 0.2425(11) 0.043(2) Uani 0.474(9) 1 d . U . A 1
H6A H 0.4509 0.3258 0.2749 0.052 Uiso 0.474(9) 1 calc R . . A 1
H6B H 0.3676 0.3807 0.2657 0.052 Uiso 0.474(9) 1 calc R . . A 1
C6' C 0.3913(15) 0.3341(17) 0.2264(11) 0.045(2) Uani 0.526(9) 1 d . U . A 2
H6'A H 0.3809 0.3723 0.2742 0.054 Uiso 0.526(9) 1 calc R . . A 2
H6'B H 0.4511 0.3230 0.2252 0.054 Uiso 0.526(9) 1 calc R . . A 2
C7 C 0.4211(11) 0.3506(10) 0.1486(10) 0.060(2) Uani 0.474(9) 1 d . U . A 1
H7A H 0.4530 0.3013 0.1262 0.072 Uiso 0.474(9) 1 calc R . . A 1
H7B H 0.3696 0.3553 0.1168 0.072 Uiso 0.474(9) 1 calc R . . A 1
C7' C 0.3727(9) 0.3823(8) 0.1565(8) 0.053(2) Uani 0.526(9) 1 d . U . A 2
H7'A H 0.3973 0.4409 0.1611 0.064 Uiso 0.526(9) 1 calc R . . A 2
H7'B H 0.3125 0.3891 0.1517 0.064 Uiso 0.526(9) 1 calc R . . A 2
C8 C 0.4707(11) 0.4345(10) 0.1389(11) 0.080(4) Uani 0.474(9) 1 d . U . A 1
H8A H 0.4363 0.4791 0.1133 0.120 Uiso 0.474(9) 1 calc GR . . A 1
H8B H 0.5186 0.4234 0.1043 0.120 Uiso 0.474(9) 1 calc GR . . A 1
H8C H 0.4888 0.4546 0.1930 0.120 Uiso 0.474(9) 1 calc GR . . A 1
C8' C 0.4046(10) 0.3386(10) 0.0827(9) 0.077(3) Uani 0.526(9) 1 d . U . A 2
H8'A H 0.3975 0.3766 0.0350 0.115 Uiso 0.526(9) 1 calc R . . A 2
H8'B H 0.3746 0.2843 0.0739 0.115 Uiso 0.526(9) 1 calc R . . A 2
H8'C H 0.4630 0.3259 0.0902 0.115 Uiso 0.526(9) 1 calc R . . A 2
C9 C -0.0428(4) 0.4033(4) 0.0000 0.0222(11) Uani 1 2 d S T P . .
C10 C 0.0650(3) 0.3296(3) 0.0434(2) 0.0227(8) Uani 1 1 d . . . . .
C11 C 0.1254(3) 0.2950(3) 0.1036(3) 0.0281(9) Uani 1 1 d . . . . .
C12 C -0.1219(4) 0.4549(4) 0.0000 0.0284(12) Uani 1 2 d S T P . .
H12A H -0.1228 0.4928 -0.0491 0.034 Uiso 0.5 1 calc R . . . .
H12B H -0.1228 0.4928 0.0491 0.034 Uiso 0.5 1 calc R . . . .
C13 C -0.1995(5) 0.3979(5) 0.0000 0.0486(18) Uani 1 2 d S T P . .
H13A H -0.1989 0.3601 -0.0491 0.058 Uiso 0.5 1 calc R . . . .
H13B H -0.1989 0.3601 0.0491 0.058 Uiso 0.5 1 calc R . . . .
C14 C -0.2784(6) 0.4523(7) 0.0000 0.086(3) Uani 1 2 d S T P . .
H14A H -0.3261 0.4136 0.0000 0.129 Uiso 1 2 calc RS T P . .
H14B H -0.2798 0.4890 -0.0491 0.129 Uiso 0.5 1 calc R . . . .
H14C H -0.2798 0.4890 0.0491 0.129 Uiso 0.5 1 calc R . . . .
C15 C 0.2118(5) 0.3198(5) 0.5000 0.0408(15) Uani 1 2 d S T P . .
C16 C 0.0892(3) 0.3607(3) 0.4572(3) 0.0311(10) Uani 1 1 d . . . . .
C17 C 0.0221(3) 0.3790(3) 0.3969(3) 0.0308(10) Uani 1 1 d . . . . .
C18 C 0.3002(5) 0.2934(6) 0.5000 0.0541(18) Uani 1 2 d S T P . .
H18A H 0.3111 0.2573 0.4509 0.065 Uiso 0.5 1 calc R . . . .
H18B H 0.3111 0.2573 0.5491 0.065 Uiso 0.5 1 calc R . . . .
C19 C 0.3597(7) 0.3713(9) 0.5000 0.088(3) Uani 1 2 d S T P . .
H19A H 0.3480 0.4073 0.4510 0.105 Uiso 0.5 1 calc R . . . .
H19B H 0.3480 0.4073 0.5490 0.105 Uiso 0.5 1 calc R . . . .
C20 C 0.4518(9) 0.3487(11) 0.5000 0.131(5) Uani 1 2 d S T P . .
H20A H 0.4841 0.4024 0.5000 0.196 Uiso 1 2 calc RS T P . .
H20B H 0.4649 0.3147 0.4509 0.196 Uiso 0.5 1 calc R . . . .
H20C H 0.4649 0.3147 0.5491 0.196 Uiso 0.5 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O2 2.178(3) 8_665 ?
Co1 O4 2.225(4) . ?
Co1 O5 2.146(3) . ?
Co1 O8 2.171(3) . ?
Co1 N1 2.058(4) . ?
Co1 N4 2.092(4) . ?
Co2 O1 2.135(3) 8_665 ?
Co2 O1 2.141(3) 7_565 ?
Co2 O5 2.174(3) . ?
Co2 O8 2.102(3) . ?
Co2 N2 2.052(4) 7_565 ?
Co2 N3 2.074(3) . ?
O1 Co2 2.135(3) 8_655 ?
O1 Co2 2.141(3) 7_665 ?
O1 C4 1.266(5) . ?
O2 Co1 2.178(3) 8_655 ?
O2 C4 1.249(5) . ?
O3 C5 1.311(7) . ?
O4 C5 1.231(6) . ?
O5 C11 1.270(5) . ?
O6 C11 1.247(5) . ?
O7 C17 1.260(6) . ?
O8 C17 1.253(5) . ?
N1 C1 1.339(6) . ?
N1 C3 1.372(6) . ?
N2 Co2 2.052(4) 7_665 ?
N2 C1 1.341(6) . ?
N2 C2 1.377(6) . ?
N3 C9 1.351(5) . ?
N3 C10 1.363(5) . ?
N4 C15 1.354(5) . ?
N4 C16 1.368(6) . ?
C1 C6 1.51(3) . ?
C1 C6' 1.50(3) . ?
C2 C3 1.365(6) . ?
C2 C4 1.487(6) . ?
C3 C5 1.462(7) . ?
C6 C7 1.56(3) . ?
C6' C7' 1.37(2) . ?
C7 C8 1.501(19) . ?
C7' C8' 1.442(19) . ?
C9 N3 1.351(5) 6 ?
C9 C12 1.483(8) . ?
C10 C10 1.385(8) 6 ?
C10 C11 1.459(6) . ?
C12 C13 1.509(9) . ?
C13 C14 1.505(12) . ?
C15 N4 1.354(5) 6_556 ?
C15 C18 1.468(10) . ?
C16 C16 1.365(8) 6_556 ?
C16 C17 1.467(6) . ?
C18 C19 1.512(15) . ?
C19 C20 1.510(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Co1 O4 173.15(14) 8_665 . ?
O5 Co1 O2 89.45(12) . 8_665 ?
O5 Co1 O4 84.38(14) . . ?
O5 Co1 O8 75.79(11) . . ?
O8 Co1 O2 87.09(13) . 8_665 ?
O8 Co1 O4 88.50(13) . . ?
N1 Co1 O2 105.41(15) . 8_665 ?
N1 Co1 O4 78.39(15) . . ?
N1 Co1 O5 97.14(14) . . ?
N1 Co1 O8 165.75(16) . . ?
N1 Co1 N4 107.03(16) . . ?
N4 Co1 O2 95.76(15) . 8_665 ?
N4 Co1 O4 88.44(16) . . ?
N4 Co1 O5 152.84(14) . . ?
N4 Co1 O8 77.88(13) . . ?
O1 Co2 O1 75.91(14) 8_665 7_565 ?
O1 Co2 O5 87.10(12) 8_665 . ?
O1 Co2 O5 162.35(12) 7_565 . ?
O8 Co2 O1 80.66(12) . 8_665 ?
O8 Co2 O1 104.75(12) . 7_565 ?
O8 Co2 O5 76.63(12) . . ?
N2 Co2 O1 78.16(13) 7_565 7_565 ?
N2 Co2 O1 149.15(14) 7_565 8_665 ?
N2 Co2 O5 119.48(14) 7_565 . ?
N2 Co2 O8 90.13(14) 7_565 . ?
N2 Co2 N3 101.43(14) 7_565 . ?
N3 Co2 O1 98.66(12) . 7_565 ?
N3 Co2 O1 98.73(13) . 8_665 ?
N3 Co2 O5 78.97(12) . . ?
N3 Co2 O8 155.60(13) . . ?
Co2 O1 Co2 103.33(14) 8_655 7_665 ?
C4 O1 Co2 136.2(3) . 8_655 ?
C4 O1 Co2 116.2(3) . 7_665 ?
C4 O2 Co1 125.4(3) . 8_655 ?
C5 O4 Co1 111.0(3) . . ?
Co1 O5 Co2 100.90(12) . . ?
C11 O5 Co1 139.4(3) . . ?
C11 O5 Co2 113.4(3) . . ?
Co2 O8 Co1 102.45(13) . . ?
C17 O8 Co1 115.8(3) . . ?
C17 O8 Co2 141.3(3) . . ?
C1 N1 Co1 142.0(3) . . ?
C1 N1 C3 104.6(4) . . ?
C3 N1 Co1 113.2(3) . . ?
C1 N2 Co2 141.5(3) . 7_665 ?
C1 N2 C2 105.7(4) . . ?
C2 N2 Co2 112.5(3) . 7_665 ?
C9 N3 Co2 143.1(3) . . ?
C9 N3 C10 105.8(3) . . ?
C10 N3 Co2 110.9(3) . . ?
C15 N4 Co1 142.8(4) . . ?
C15 N4 C16 105.3(4) . . ?
C16 N4 Co1 111.1(3) . . ?
N1 C1 N2 112.8(4) . . ?
N1 C1 C6 124.8(10) . . ?
N1 C1 C6' 123.0(10) . . ?
N2 C1 C6 121.9(11) . . ?
N2 C1 C6' 124.0(10) . . ?
N2 C2 C4 118.4(4) . . ?
C3 C2 N2 107.3(4) . . ?
C3 C2 C4 134.3(4) . . ?
N1 C3 C5 116.8(4) . . ?
C2 C3 N1 109.6(4) . . ?
C2 C3 C5 133.6(5) . . ?
O1 C4 C2 113.1(4) . . ?
O2 C4 O1 125.9(4) . . ?
O2 C4 C2 121.0(4) . . ?
O3 C5 C3 117.8(5) . . ?
O4 C5 O3 121.8(5) . . ?
O4 C5 C3 120.4(5) . . ?
C1 C6 C7 106.9(14) . . ?
C7' C6' C1 122.1(16) . . ?
C8 C7 C6 111.3(15) . . ?
C6' C7' C8' 110.4(15) . . ?
N3 C9 N3 112.0(5) 6 . ?
N3 C9 C12 124.0(3) . . ?
N3 C9 C12 124.0(3) 6 . ?
N3 C10 C10 108.3(2) . 6 ?
N3 C10 C11 120.4(4) . . ?
C10 C10 C11 131.2(2) 6 . ?
O5 C11 C10 115.8(4) . . ?
O6 C11 O5 123.8(4) . . ?
O6 C11 C10 120.5(4) . . ?
C9 C12 C13 113.6(5) . . ?
C14 C13 C12 112.2(7) . . ?
N4 C15 N4 111.9(6) 6_556 . ?
N4 C15 C18 124.0(3) 6_556 . ?
N4 C15 C18 124.0(3) . . ?
N4 C16 C17 120.1(4) . . ?
C16 C16 N4 108.7(2) 6_556 . ?
C16 C16 C17 131.0(2) 6_556 . ?
O7 C17 C16 120.6(4) . . ?
O8 C17 O7 124.6(4) . . ?
O8 C17 C16 114.8(4) . . ?
C15 C18 C19 113.2(8) . . ?
C20 C19 C18 115.9(11) . . ?

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