# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_1
_audit_block_doi                 10.5517/cc1k8gr1
_database_code_depnum_ccdc_archive 'CCDC 1438113'
_audit_update_record             
;
2015-11-20 deposited with the CCDC.
2016-01-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H11 Co N O6'
_chemical_formula_weight         336.16

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.876(2)
_cell_length_b                   12.212(2)
_cell_length_c                   7.7376(15)
_cell_angle_alpha                90
_cell_angle_beta                 104.205(18)
_cell_angle_gamma                90
_cell_volume                     1271.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    945
_cell_measurement_theta_min      2.7100
_cell_measurement_theta_max      28.9464

_exptl_crystal_description       sheet
_exptl_crystal_colour            pinkish
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.757
_exptl_crystal_F_000             684
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    1.379
_shelx_estimated_absorpt_T_min   0.675
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3844
_diffrn_reflns_av_unetI/netI     0.1050
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.029
_diffrn_reflns_theta_max         25.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2496
_reflns_number_gt                1713
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0925P)²+3.5210P] 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_number_reflns         2496
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1275
_refine_ls_R_factor_gt           0.0896
_refine_ls_wR_factor_ref         0.2257
_refine_ls_wR_factor_gt          0.2021
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_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 0.66277(7) 0.09866(8) 0.82009(13) 0.0274(4) Uani 1 1 d . . . . .
O1 O 0.5536(4) 0.2072(5) 0.7452(8) 0.0425(15) Uani 1 1 d . . . . .
O2 O 0.4541(5) 0.0689(5) 0.6448(9) 0.0502(17) Uani 1 1 d . . . . .
O3 O -0.2124(4) 0.3124(5) -0.1147(8) 0.0433(15) Uani 1 1 d . . . . .
O4 O -0.1915(4) 0.1316(5) -0.0903(8) 0.0420(15) Uani 1 1 d . . . . .
O1W O 0.6516(4) 0.1318(5) 1.0862(7) 0.0438(16) Uani 1 1 d . . . . .
O2W O 0.6802(5) 0.0650(5) 0.5666(8) 0.0490(17) Uani 1 1 d . . . . .
N1 N 0.3330(4) 0.4350(5) 0.6014(8) 0.0275(14) Uani 1 1 d . . . . .
C1 C 0.4031(5) 0.3576(7) 0.6533(9) 0.0278(17) Uani 1 1 d . . . . .
H1A H 0.4632 0.3769 0.7306 0.033 Uiso 1 1 calc R U . . .
C2 C 0.3888(5) 0.2493(6) 0.5955(10) 0.0248(16) Uani 1 1 d . . . . .
C3 C 0.2994(5) 0.2213(6) 0.4762(10) 0.0277(17) Uani 1 1 d . . . . .
H3A H 0.2878 0.1493 0.4379 0.033 Uiso 1 1 calc R U . . .
C4 C 0.2270(6) 0.3013(7) 0.4143(9) 0.0281(17) Uani 1 1 d . . . . .
C5 C 0.2479(5) 0.4060(6) 0.4830(10) 0.0319(18) Uani 1 1 d . . . . .
H5A H 0.2001 0.4599 0.4450 0.038 Uiso 1 1 calc R U . . .
C6 C 0.1307(5) 0.2803(6) 0.2838(9) 0.0252(17) Uani 1 1 d . . . . .
C7 C 0.0934(6) 0.1753(7) 0.2458(10) 0.0346(19) Uani 1 1 d . . . . .
H7A H 0.1313 0.1157 0.2982 0.042 Uiso 1 1 calc R U . . .
C8 C 0.0023(6) 0.1576(7) 0.1330(11) 0.0347(19) Uani 1 1 d . . . . .
H8A H -0.0199 0.0862 0.1071 0.042 Uiso 1 1 calc R U . . .
C9 C -0.0583(5) 0.2452(7) 0.0559(9) 0.0290(18) Uani 1 1 d . . . . .
C10 C -0.0205(6) 0.3494(7) 0.0908(11) 0.039(2) Uani 1 1 d . . . . .
H10A H -0.0582 0.4095 0.0402 0.046 Uiso 1 1 calc R U . . .
C11 C 0.0737(6) 0.3651(8) 0.2016(12) 0.043(2) Uani 1 1 d . . . . .
H11A H 0.0988 0.4359 0.2201 0.052 Uiso 1 1 calc R U . . .
C12 C 0.4690(6) 0.1669(7) 0.6654(10) 0.0301(18) Uani 1 1 d . . . . .
C13 C -0.1611(5) 0.2278(7) -0.0590(10) 0.0320(19) 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 1.989(5) . ?
Co1 O4 2.010(5) 1_656 ?
Co1 O2W 2.075(6) . ?
Co1 N1 2.085(6) 2_646 ?
Co1 O1W 2.141(6) . ?
O1 C12 1.283(9) . ?
O2 C12 1.218(10) . ?
O3 C13 1.268(10) . ?
O4 C13 1.252(10) . ?
O4 Co1 2.010(5) 1_454 ?
N1 C1 1.345(9) . ?
N1 C5 1.352(9) . ?
N1 Co1 2.086(6) 2_656 ?
C1 C2 1.394(11) . ?
C1 H1A 0.9300 . ?
C2 C3 1.395(10) . ?
C2 C12 1.500(10) . ?
C3 C4 1.398(10) . ?
C3 H3A 0.9300 . ?
C4 C5 1.387(10) . ?
C4 C6 1.487(10) . ?
C5 H5A 0.9300 . ?
C6 C11 1.361(11) . ?
C6 C7 1.387(11) . ?
C7 C8 1.366(11) . ?
C7 H7A 0.9300 . ?
C8 C9 1.400(11) . ?
C8 H8A 0.9300 . ?
C9 C10 1.378(12) . ?
C9 C13 1.500(10) . ?
C10 C11 1.390(11) . ?
C10 H10A 0.9300 . ?
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
O1 Co1 O4 126.6(2) . 1_656 ?
O1 Co1 O2W 96.5(3) . . ?
O4 Co1 O2W 91.4(3) 1_656 . ?
O1 Co1 N1 133.5(2) . 2_646 ?
O4 Co1 N1 97.9(2) 1_656 2_646 ?
O2W Co1 N1 94.8(3) . 2_646 ?
O1 Co1 O1W 85.7(2) . . ?
O4 Co1 O1W 86.2(2) 1_656 . ?
O2W Co1 O1W 177.5(2) . . ?
N1 Co1 O1W 84.5(3) 2_646 . ?
C12 O1 Co1 115.2(5) . . ?
C13 O4 Co1 121.2(5) . 1_454 ?
C1 N1 C5 117.7(6) . . ?
C1 N1 Co1 128.3(5) . 2_656 ?
C5 N1 Co1 114.0(5) . 2_656 ?
N1 C1 C2 122.4(7) . . ?
N1 C1 H1A 118.8 . . ?
C2 C1 H1A 118.8 . . ?
C1 C2 C3 118.6(7) . . ?
C1 C2 C12 119.1(6) . . ?
C3 C2 C12 122.3(7) . . ?
C2 C3 C4 120.2(7) . . ?
C2 C3 H3A 119.9 . . ?
C4 C3 H3A 119.9 . . ?
C5 C4 C3 116.6(7) . . ?
C5 C4 C6 119.2(7) . . ?
C3 C4 C6 124.2(7) . . ?
N1 C5 C4 124.6(7) . . ?
N1 C5 H5A 117.7 . . ?
C4 C5 H5A 117.7 . . ?
C11 C6 C7 117.4(7) . . ?
C11 C6 C4 120.6(7) . . ?
C7 C6 C4 122.0(7) . . ?
C8 C7 C6 121.3(8) . . ?
C8 C7 H7A 119.3 . . ?
C6 C7 H7A 119.3 . . ?
C7 C8 C9 121.1(8) . . ?
C7 C8 H8A 119.5 . . ?
C9 C8 H8A 119.4 . . ?
C10 C9 C8 117.6(7) . . ?
C10 C9 C13 120.5(8) . . ?
C8 C9 C13 122.0(8) . . ?
C9 C10 C11 120.2(8) . . ?
C9 C10 H10A 119.9 . . ?
C11 C10 H10A 119.9 . . ?
C6 C11 C10 122.3(8) . . ?
C6 C11 H11A 118.9 . . ?
C10 C11 H11A 118.9 . . ?
O2 C12 O1 123.0(7) . . ?
O2 C12 C2 121.7(7) . . ?
O1 C12 C2 115.2(7) . . ?
O4 C13 O3 124.4(7) . . ?
O4 C13 C9 118.3(7) . . ?
O3 C13 C9 117.3(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -2.9(11) . . . . ?
Co1 N1 C1 C2 177.3(5) 2_656 . . . ?
N1 C1 C2 C3 1.5(11) . . . . ?
N1 C1 C2 C12 -177.5(7) . . . . ?
C1 C2 C3 C4 1.3(11) . . . . ?
C12 C2 C3 C4 -179.7(7) . . . . ?
C2 C3 C4 C5 -2.5(11) . . . . ?
C2 C3 C4 C6 178.3(7) . . . . ?
C1 N1 C5 C4 1.5(12) . . . . ?
Co1 N1 C5 C4 -178.6(6) 2_656 . . . ?
C3 C4 C5 N1 1.2(11) . . . . ?
C6 C4 C5 N1 -179.6(7) . . . . ?
C5 C4 C6 C11 14.9(11) . . . . ?
C3 C4 C6 C11 -166.0(8) . . . . ?
C5 C4 C6 C7 -162.6(7) . . . . ?
C3 C4 C6 C7 16.5(11) . . . . ?
C11 C6 C7 C8 -1.2(12) . . . . ?
C4 C6 C7 C8 176.3(7) . . . . ?
C6 C7 C8 C9 -2.0(12) . . . . ?
C7 C8 C9 C10 3.2(11) . . . . ?
C7 C8 C9 C13 -176.1(7) . . . . ?
C8 C9 C10 C11 -1.1(12) . . . . ?
C13 C9 C10 C11 178.2(8) . . . . ?
C7 C6 C11 C10 3.4(13) . . . . ?
C4 C6 C11 C10 -174.3(8) . . . . ?
C9 C10 C11 C6 -2.2(14) . . . . ?
Co1 O1 C12 O2 3.9(10) . . . . ?
Co1 O1 C12 C2 -175.1(5) . . . . ?
C1 C2 C12 O2 166.9(8) . . . . ?
C3 C2 C12 O2 -12.1(12) . . . . ?
C1 C2 C12 O1 -14.0(10) . . . . ?
C3 C2 C12 O1 167.0(7) . . . . ?
Co1 O4 C13 O3 -16.0(11) 1_454 . . . ?
Co1 O4 C13 C9 162.2(5) 1_454 . . . ?
C10 C9 C13 O4 178.5(8) . . . . ?
C8 C9 C13 O4 -2.3(11) . . . . ?
C10 C9 C13 O3 -3.1(11) . . . . ?
C8 C9 C13 O3 176.1(7) . . . . ?

_refine_diff_density_max         2.251
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.146

####################################################################### 
# 
# 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
_audit_block_doi                 10.5517/cc1k8gs2
_database_code_depnum_ccdc_archive 'CCDC 1438114'
_audit_update_record             
;
2015-11-20 deposited with the CCDC.
2016-01-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H11 Co N O6'
_chemical_formula_weight         336.16

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 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'
'-x, -y, -z'

_cell_length_a                   6.4032(3)
_cell_length_b                   7.7936(3)
_cell_length_c                   12.7782(6)
_cell_angle_alpha                74.095(4)
_cell_angle_beta                 83.775(4)
_cell_angle_gamma                84.040(4)
_cell_volume                     607.81(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2342
_cell_measurement_theta_min      2.7203
_cell_measurement_theta_max      28.9590

_exptl_crystal_description       plank
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.837
_exptl_crystal_F_000             342
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.442
_shelx_estimated_absorpt_T_min   0.893
_shelx_estimated_absorpt_T_max   0.931
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4445
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.726
_diffrn_reflns_theta_max         26.990
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2602
_reflns_number_gt                2286
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0372P)²+0.1366P] 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_number_reflns         2602
_refine_ls_number_parameters     206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0804
_refine_ls_wR_factor_gt          0.0766
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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 0.52508(5) 0.67133(4) 0.89013(2) 0.01823(11) Uani 1 1 d . . . . .
N1 N 1.2171(3) 0.4749(3) 1.17817(14) 0.0188(4) Uani 1 1 d . . . . .
O1 O 0.6392(2) 0.5762(2) 1.04710(12) 0.0191(3) Uani 1 1 d . . . . .
O2 O 0.5667(3) 0.8161(2) 1.11248(14) 0.0325(4) Uani 1 1 d . . . . .
O3 O 1.4065(3) 0.7347(2) 1.74127(13) 0.0299(4) Uani 1 1 d . . . . .
O4 O 1.0939(3) 0.8834(2) 1.75747(13) 0.0263(4) Uani 1 1 d . . . . .
O1W O 0.6993(3) 0.8955(3) 0.85526(18) 0.0367(5) Uani 1 1 d . . . . .
O2W O 0.2634(3) 0.8147(3) 0.95074(16) 0.0284(4) Uani 1 1 d . . . . .
C1 C 1.0311(4) 0.5113(3) 1.13521(17) 0.0187(5) Uani 1 1 d . . . . .
H1A H 1.0063 0.4547 1.0829 0.022 Uiso 1 1 calc R U . . .
C2 C 0.8730(3) 0.6295(3) 1.16474(17) 0.0172(5) Uani 1 1 d . . . . .
C3 C 0.9068(3) 0.7063(3) 1.24714(17) 0.0187(5) Uani 1 1 d . . . . .
H3A H 0.8053 0.7882 1.2674 0.022 Uiso 1 1 calc R U . . .
C4 C 1.0923(4) 0.6607(3) 1.29916(17) 0.0194(5) Uani 1 1 d . . . . .
C5 C 1.2440(4) 0.5476(3) 1.25956(18) 0.0214(5) Uani 1 1 d . . . . .
H5A H 1.3717 0.5206 1.2912 0.026 Uiso 1 1 calc R U . . .
C6 C 1.1287(4) 0.7175(3) 1.39804(17) 0.0198(5) Uani 1 1 d . . . . .
C7 C 1.3296(4) 0.7255(4) 1.4255(2) 0.0341(6) Uani 1 1 d . . . . .
H7A H 1.4448 0.7106 1.3769 0.041 Uiso 1 1 calc R U . . .
C8 C 1.3624(4) 0.7554(4) 1.5245(2) 0.0329(6) Uani 1 1 d . . . . .
H8A H 1.4990 0.7555 1.5428 0.040 Uiso 1 1 calc R U . . .
C9 C 1.1927(4) 0.7852(3) 1.59639(17) 0.0195(5) Uani 1 1 d . . . . .
C10 C 0.9907(4) 0.7884(3) 1.56637(18) 0.0222(5) Uani 1 1 d . . . . .
H10A H 0.8753 0.8156 1.6114 0.027 Uiso 1 1 calc R U . . .
C11 C 0.9599(4) 0.7510(3) 1.46895(19) 0.0237(5) Uani 1 1 d . . . . .
H11A H 0.8234 0.7485 1.4512 0.028 Uiso 1 1 calc R U . . .
C12 C 0.6766(3) 0.6802(3) 1.10495(17) 0.0182(5) Uani 1 1 d . . . . .
C13 C 1.2317(4) 0.8044(3) 1.70680(17) 0.0193(5) Uani 1 1 d . . . . .
H1WB H 0.644(5) 0.978(4) 0.849(3) 0.038(10) Uiso 1 1 d . . . . .
H1WA H 0.821(6) 0.903(5) 0.811(3) 0.080(13) Uiso 1 1 d . . . . .
H2WB H 0.294(6) 0.885(5) 0.974(3) 0.067(13) Uiso 1 1 d . . . . .
H2WA H 0.199(6) 0.857(5) 0.901(3) 0.073(14) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O3 2.0394(16) 1_454 ?
Co1 O1W 2.090(2) . ?
Co1 O2W 2.1115(19) . ?
Co1 O1 2.1207(15) . ?
Co1 N1 2.1511(18) 2_767 ?
Co1 O1 2.2050(15) 2_667 ?
N1 C1 1.337(3) . ?
N1 C5 1.347(3) . ?
N1 Co1 2.1511(18) 2_767 ?
O1 C12 1.291(3) . ?
O1 Co1 2.2050(15) 2_667 ?
O2 C12 1.230(3) . ?
O3 C13 1.262(3) . ?
O3 Co1 2.0394(16) 1_656 ?
O4 C13 1.248(3) . ?
C1 C2 1.389(3) . ?
C2 C3 1.392(3) . ?
C2 C12 1.504(3) . ?
C3 C4 1.390(3) . ?
C4 C5 1.392(3) . ?
C4 C6 1.496(3) . ?
C6 C7 1.382(3) . ?
C6 C11 1.384(3) . ?
C7 C8 1.388(3) . ?
C8 C9 1.388(3) . ?
C9 C10 1.384(3) . ?
C9 C13 1.508(3) . ?
C10 C11 1.392(3) . ?

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
O3 Co1 O1W 95.14(8) 1_454 . ?
O3 Co1 O2W 90.25(7) 1_454 . ?
O1W Co1 O2W 90.36(8) . . ?
O3 Co1 O1 173.66(6) 1_454 . ?
O1W Co1 O1 90.89(8) . . ?
O2W Co1 O1 91.68(7) . . ?
O3 Co1 N1 87.06(7) 1_454 2_767 ?
O1W Co1 N1 90.72(8) . 2_767 ?
O2W Co1 N1 177.18(8) . 2_767 ?
O1 Co1 N1 90.90(6) . 2_767 ?
O3 Co1 O1 94.04(7) 1_454 2_667 ?
O1W Co1 O1 170.82(7) . 2_667 ?
O2W Co1 O1 89.45(7) . 2_667 ?
O1 Co1 O1 79.95(6) . 2_667 ?
N1 Co1 O1 89.89(6) 2_767 2_667 ?
C1 N1 C5 117.43(19) . . ?
C1 N1 Co1 121.53(14) . 2_767 ?
C5 N1 Co1 120.75(15) . 2_767 ?
C12 O1 Co1 123.36(14) . . ?
C12 O1 Co1 125.05(14) . 2_667 ?
Co1 O1 Co1 100.05(6) . 2_667 ?
C13 O3 Co1 133.78(14) . 1_656 ?
N1 C1 C2 123.27(19) . . ?
C1 C2 C3 118.1(2) . . ?
C1 C2 C12 120.73(18) . . ?
C3 C2 C12 121.1(2) . . ?
C4 C3 C2 120.0(2) . . ?
C3 C4 C5 117.07(19) . . ?
C3 C4 C6 123.3(2) . . ?
C5 C4 C6 119.5(2) . . ?
N1 C5 C4 123.9(2) . . ?
C7 C6 C11 118.2(2) . . ?
C7 C6 C4 121.5(2) . . ?
C11 C6 C4 120.2(2) . . ?
C6 C7 C8 121.0(2) . . ?
C9 C8 C7 120.5(2) . . ?
C10 C9 C8 118.7(2) . . ?
C10 C9 C13 121.6(2) . . ?
C8 C9 C13 119.6(2) . . ?
C9 C10 C11 120.2(2) . . ?
C6 C11 C10 121.2(2) . . ?
O2 C12 O1 124.9(2) . . ?
O2 C12 C2 119.02(19) . . ?
O1 C12 C2 116.02(19) . . ?
O4 C13 O3 124.9(2) . . ?
O4 C13 C9 119.8(2) . . ?
O3 C13 C9 115.32(19) . . ?

_refine_diff_density_max         0.366
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.072

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

data_3
_audit_block_doi                 10.5517/cc1k8gt3
_database_code_depnum_ccdc_archive 'CCDC 1438115'
_audit_update_record             
;
2015-11-20 deposited with the CCDC.
2016-01-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H11 Co N O6'
_chemical_formula_weight         336.16

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 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'
'-x, -y, -z'

_cell_length_a                   6.4023(3)
_cell_length_b                   16.0344(6)
_cell_length_c                   25.6980(10)
_cell_angle_alpha                106.5880(10)
_cell_angle_beta                 96.0840(10)
_cell_angle_gamma                92.9930(10)
_cell_volume                     2504.62(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.783
_exptl_crystal_F_000             1368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.399
_shelx_estimated_absorpt_T_min   0.598
_shelx_estimated_absorpt_T_max   0.873
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14831
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.330
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             10595
_reflns_number_gt                8195
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0847P)²+0.2082P] 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_number_reflns         10595
_refine_ls_number_parameters     757
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1419
_refine_ls_wR_factor_gt          0.1313
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001

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 0.04822(7) 0.13745(3) 0.46527(2) 0.01729(12) Uani 1 1 d . . . . .
Co2 Co -1.05829(7) -0.35045(3) 0.47919(2) 0.01818(12) Uani 1 1 d . . . . .
Co3 Co -1.51630(7) -0.33029(3) 0.02937(2) 0.01755(12) Uani 1 1 d . . . . .
Co4 Co -1.48608(7) -0.17587(3) -0.03281(2) 0.01811(12) Uani 1 1 d . . . . .
O1 O -1.3178(4) -0.21640(14) 0.03408(9) 0.0198(5) Uani 1 1 d . . . . .
O2 O -1.3087(4) -0.09461(16) 0.10416(10) 0.0308(6) Uani 1 1 d . . . . .
O3 O -0.4072(4) -0.00105(16) 0.43367(9) 0.0270(6) Uani 1 1 d . . . . .
O4 O -0.1318(4) 0.04645(16) 0.40009(9) 0.0270(6) Uani 1 1 d . . . . .
O5 O -0.2317(3) -0.24457(14) 0.47042(9) 0.0192(5) Uani 1 1 d . . . . .
O6 O -0.2144(4) -0.19840(17) 0.39638(10) 0.0304(6) Uani 1 1 d . . . . .
O7 O -1.0884(4) -0.43449(16) 0.06732(9) 0.0269(6) Uani 1 1 d . . . . .
O8 O -1.3529(4) -0.35572(17) 0.09600(9) 0.0277(6) Uani 1 1 d . . . . .
O9 O -2.8840(4) -0.30043(18) -0.38563(10) 0.0337(6) Uani 1 1 d . . . . .
O10 O -2.8803(3) -0.24443(14) -0.45588(9) 0.0193(5) Uani 1 1 d . . . . .
O11 O -1.6587(4) -0.15113(16) -0.09882(9) 0.0262(5) Uani 1 1 d . . . . .
O12 O -1.9027(4) -0.06757(16) -0.06178(9) 0.0262(5) Uani 1 1 d . . . . .
O13 O -1.6839(4) -0.28911(14) -0.03678(9) 0.0195(5) Uani 1 1 d . . . . .
O14 O -1.6843(4) -0.40714(16) -0.10864(10) 0.0324(6) Uani 1 1 d . . . . .
O15 O -2.4856(4) -0.50851(17) -0.44370(10) 0.0324(6) Uani 1 1 d . . . . .
O16 O -2.7743(4) -0.55360(18) -0.41572(10) 0.0330(6) Uani 1 1 d . . . . .
O1W O -0.1187(4) 0.12655(16) 0.52922(10) 0.0278(6) Uani 1 1 d . . . . .
O2W O 0.2567(4) 0.04957(16) 0.48160(10) 0.0267(5) Uani 1 1 d . . . . .
O3W O -1.2373(4) -0.36409(15) 0.54115(10) 0.0272(6) Uani 1 1 d . . . . .
O4W O -0.8395(4) -0.43079(17) 0.49986(11) 0.0342(6) Uani 1 1 d . . . . .
O5W O -1.7476(4) -0.43348(15) 0.01668(10) 0.0262(5) Uani 1 1 d . . . . .
O6W O -1.3623(4) -0.40624(16) -0.03356(10) 0.0274(6) Uani 1 1 d . . . . .
O7W O -1.6422(4) -0.10063(16) 0.03033(10) 0.0296(6) Uani 1 1 d . . . . .
O8W O -1.2595(4) -0.07181(15) -0.01883(10) 0.0283(6) Uani 1 1 d . . . . .
N1 N -0.7051(4) -0.25438(17) 0.08723(11) 0.0191(6) Uani 1 1 d . . . . .
N2 N -0.8580(4) -0.33500(17) 0.41935(11) 0.0203(6) Uani 1 1 d . . . . .
N3 N -2.2514(4) -0.15469(17) -0.40691(10) 0.0182(6) Uani 1 1 d . . . . .
N4 N -2.2957(4) -0.25131(17) -0.09155(11) 0.0192(6) Uani 1 1 d . . . . .
C1 C -0.9047(5) -0.2408(2) 0.07054(13) 0.0193(7) Uani 1 1 d . . . . .
H1A H -0.9670 -0.2736 0.0359 0.023 Uiso 1 1 calc R U . . .
C2 C -1.0201(5) -0.1806(2) 0.10245(13) 0.0193(7) Uani 1 1 d . . . . .
C3 C -0.9298(5) -0.1348(2) 0.15534(13) 0.0223(7) Uani 1 1 d . . . . .
H3A H -1.0036 -0.0935 0.1777 0.027 Uiso 1 1 calc R U . . .
C4 C -0.7305(5) -0.1508(2) 0.17460(13) 0.0216(7) Uani 1 1 d . . . . .
C5 C -0.6252(5) -0.2106(2) 0.13850(13) 0.0223(7) Uani 1 1 d . . . . .
H5A H -0.4899 -0.2209 0.1509 0.027 Uiso 1 1 calc R U . . .
C6 C -0.6269(5) -0.1076(2) 0.23122(13) 0.0222(7) Uani 1 1 d . . . . .
C7 C -0.7329(6) -0.1033(3) 0.27603(15) 0.0307(8) Uani 1 1 d . . . . .
H7A H -0.8731 -0.1256 0.2707 0.037 Uiso 1 1 calc R U . . .
C8 C -0.6316(6) -0.0662(2) 0.32878(14) 0.0295(8) Uani 1 1 d . . . . .
H8A H -0.7042 -0.0641 0.3586 0.035 Uiso 1 1 calc R U . . .
C9 C -0.4224(5) -0.0321(2) 0.33744(13) 0.0215(7) Uani 1 1 d . . . . .
C10 C -0.3183(6) -0.0342(3) 0.29256(14) 0.0310(9) Uani 1 1 d . . . . .
H10A H -0.1799 -0.0098 0.2978 0.037 Uiso 1 1 calc R U . . .
C11 C -0.4191(6) -0.0724(3) 0.23984(14) 0.0344(9) Uani 1 1 d . . . . .
H11A H -0.3468 -0.0743 0.2100 0.041 Uiso 1 1 calc R U . . .
C12 C -1.2312(5) -0.1613(2) 0.07972(13) 0.0192(7) Uani 1 1 d . . . . .
C13 C -0.3131(5) 0.0071(2) 0.39473(13) 0.0208(7) Uani 1 1 d . . . . .
C14 C -0.6549(5) -0.3045(2) 0.43524(13) 0.0202(7) Uani 1 1 d . . . . .
H14A H -0.5980 -0.3000 0.4709 0.024 Uiso 1 1 calc R U . . .
C15 C -0.5259(5) -0.2795(2) 0.40157(13) 0.0197(7) Uani 1 1 d . . . . .
C16 C -0.6095(5) -0.2894(2) 0.34777(13) 0.0232(7) Uani 1 1 d . . . . .
H16A H -0.5278 -0.2718 0.3243 0.028 Uiso 1 1 calc R U . . .
C17 C -0.8144(6) -0.3254(2) 0.32914(14) 0.0246(7) Uani 1 1 d . . . . .
C18 C -0.9313(5) -0.3455(2) 0.36675(13) 0.0229(7) Uani 1 1 d . . . . .
H18A H -1.0707 -0.3679 0.3548 0.027 Uiso 1 1 calc R U . . .
C19 C -0.9091(5) -0.3409(2) 0.27139(13) 0.0236(7) Uani 1 1 d . . . . .
C20 C -0.7965(6) -0.3788(3) 0.22893(15) 0.0318(9) Uani 1 1 d . . . . .
H20A H -0.6605 -0.3935 0.2366 0.038 Uiso 1 1 calc R U . . .
C21 C -0.8852(6) -0.3950(3) 0.17466(14) 0.0304(8) Uani 1 1 d . . . . .
H21A H -0.8090 -0.4213 0.1464 0.036 Uiso 1 1 calc R U . . .
C22 C -1.0875(5) -0.3720(2) 0.16255(13) 0.0208(7) Uani 1 1 d . . . . .
C23 C -1.1970(6) -0.3328(3) 0.20536(14) 0.0319(9) Uani 1 1 d . . . . .
H23A H -1.3315 -0.3164 0.1979 0.038 Uiso 1 1 calc R U . . .
C24 C -1.1092(6) -0.3177(3) 0.25922(14) 0.0333(9) Uani 1 1 d . . . . .
H24A H -1.1857 -0.2916 0.2875 0.040 Uiso 1 1 calc R U . . .
C25 C -0.3068(5) -0.2375(2) 0.42332(13) 0.0197(7) Uani 1 1 d . . . . .
C26 C -1.1825(5) -0.3890(2) 0.10414(13) 0.0193(7) Uani 1 1 d . . . . .
C27 C -2.4563(5) -0.1850(2) -0.42214(12) 0.0182(7) Uani 1 1 d . . . . .
H27A H -2.5178 -0.1863 -0.4568 0.022 Uiso 1 1 calc R U . . .
C28 C -2.5784(5) -0.2140(2) -0.38879(13) 0.0191(7) Uani 1 1 d . . . . .
C29 C -2.4888(5) -0.2084(2) -0.33559(13) 0.0222(7) Uani 1 1 d . . . . .
H29A H -2.5669 -0.2284 -0.3123 0.027 Uiso 1 1 calc R U . . .
C30 C -2.2828(5) -0.1730(2) -0.31805(13) 0.0217(7) Uani 1 1 d . . . . .
C31 C -2.1708(5) -0.1483(2) -0.35544(13) 0.0215(7) Uani 1 1 d . . . . .
H31A H -2.0312 -0.1259 -0.3441 0.026 Uiso 1 1 calc R U . . .
C32 C -2.1725(5) -0.1613(2) -0.26211(13) 0.0229(7) Uani 1 1 d . . . . .
C33 C -2.2614(6) -0.1185(3) -0.21578(14) 0.0288(8) Uani 1 1 d . . . . .
H33A H -2.3964 -0.1003 -0.2193 0.035 Uiso 1 1 calc R U . . .
C34 C -2.1485(6) -0.1029(2) -0.16410(14) 0.0279(8) Uani 1 1 d . . . . .
H34A H -2.2077 -0.0730 -0.1333 0.034 Uiso 1 1 calc R U . . .
C35 C -1.9489(5) -0.1312(2) -0.15779(13) 0.0201(7) Uani 1 1 d . . . . .
C36 C -1.8620(6) -0.1753(3) -0.20429(14) 0.0297(8) Uani 1 1 d . . . . .
H36A H -1.7288 -0.1952 -0.2009 0.036 Uiso 1 1 calc R U . . .
C37 C -1.9740(6) -0.1895(3) -0.25568(14) 0.0312(9) Uani 1 1 d . . . . .
H37A H -1.9141 -0.2187 -0.2865 0.037 Uiso 1 1 calc R U . . .
C38 C -2.7978(5) -0.2565(2) -0.41059(13) 0.0204(7) Uani 1 1 d . . . . .
C39 C -1.8266(5) -0.1152(2) -0.10201(13) 0.0210(7) Uani 1 1 d . . . . .
C40 C -2.0989(5) -0.2658(2) -0.07383(13) 0.0201(7) Uani 1 1 d . . . . .
H40A H -2.0415 -0.2350 -0.0383 0.024 Uiso 1 1 calc R U . . .
C41 C -1.9781(5) -0.3237(2) -0.10557(13) 0.0193(7) Uani 1 1 d . . . . .
C42 C -2.0615(5) -0.3676(2) -0.15916(13) 0.0233(7) Uani 1 1 d . . . . .
H42A H -1.9857 -0.4086 -0.1811 0.028 Uiso 1 1 calc R U . . .
C43 C -2.2585(5) -0.3502(2) -0.18015(13) 0.0224(7) Uani 1 1 d . . . . .
C44 C -2.3690(5) -0.2927(2) -0.14419(13) 0.0231(7) Uani 1 1 d . . . . .
H44A H -2.5029 -0.2821 -0.1574 0.028 Uiso 1 1 calc R U . . .
C45 C -2.3464(5) -0.3920(2) -0.23821(14) 0.0250(8) Uani 1 1 d . . . . .
C46 C -2.2164(6) -0.4036(2) -0.27898(14) 0.0287(8) Uani 1 1 d . . . . .
H46A H -2.0737 -0.3850 -0.2696 0.034 Uiso 1 1 calc R U . . .
C47 C -2.2949(6) -0.4424(2) -0.33366(14) 0.0275(8) Uani 1 1 d . . . . .
H47A H -2.2048 -0.4499 -0.3604 0.033 Uiso 1 1 calc R U . . .
C48 C -2.5077(6) -0.4698(2) -0.34825(13) 0.0232(7) Uani 1 1 d . . . . .
C49 C -2.6400(6) -0.4581(3) -0.30754(15) 0.0353(10) Uani 1 1 d . . . . .
H49A H -2.7830 -0.4761 -0.3170 0.042 Uiso 1 1 calc R U . . .
C50 C -2.5603(6) -0.4196(3) -0.25292(14) 0.0348(9) Uani 1 1 d . . . . .
H50A H -2.6500 -0.4122 -0.2261 0.042 Uiso 1 1 calc R U . . .
C51 C -1.7652(5) -0.3424(2) -0.08299(13) 0.0206(7) Uani 1 1 d . . . . .
C52 C -2.5952(6) -0.5138(2) -0.40754(13) 0.0221(7) 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 2.069(2) . ?
Co1 O2W 2.088(2) . ?
Co1 O1W 2.095(2) . ?
Co1 O10 2.128(2) 2_255 ?
Co1 N3 2.152(3) 2_355 ?
Co1 O5 2.195(2) 2_556 ?
Co2 O16 2.049(2) 2_145 ?
Co2 O4W 2.080(3) . ?
Co2 O3W 2.111(2) . ?
Co2 O5 2.128(2) 1_455 ?
Co2 N2 2.162(3) . ?
Co2 O10 2.179(2) 1_756 ?
Co3 O8 2.063(2) . ?
Co3 O5W 2.091(2) . ?
Co3 O6W 2.100(2) . ?
Co3 O1 2.136(2) . ?
Co3 N1 2.158(3) 1_455 ?
Co3 O13 2.192(2) . ?
Co4 O11 2.071(2) . ?
Co4 O8W 2.076(2) . ?
Co4 O7W 2.107(2) . ?
Co4 O13 2.130(2) . ?
Co4 N4 2.175(3) 1_655 ?
Co4 O1 2.204(2) . ?
O1 C12 1.297(4) . ?
O2 C12 1.234(4) . ?
O3 C13 1.255(4) . ?
O4 C13 1.267(4) . ?
O5 C25 1.292(4) . ?
O5 Co2 2.128(2) 1_655 ?
O5 Co1 2.195(2) 2_556 ?
O6 C25 1.233(4) . ?
O7 C26 1.250(4) . ?
O8 C26 1.263(4) . ?
O9 C38 1.227(4) . ?
O10 C38 1.296(4) . ?
O10 Co1 2.128(2) 2_255 ?
O10 Co2 2.179(2) 1_354 ?
O11 C39 1.252(4) . ?
O12 C39 1.259(4) . ?
O13 C51 1.287(4) . ?
O14 C51 1.232(4) . ?
O15 C52 1.241(4) . ?
O16 C52 1.250(4) . ?
O16 Co2 2.049(2) 2_145 ?
N1 C5 1.335(4) . ?
N1 C1 1.353(4) . ?
N1 Co3 2.158(3) 1_655 ?
N2 C14 1.343(4) . ?
N2 C18 1.343(4) . ?
N3 C31 1.341(4) . ?
N3 C27 1.352(4) . ?
N3 Co1 2.152(3) 2_355 ?
N4 C44 1.346(4) . ?
N4 C40 1.348(4) . ?
N4 Co4 2.175(3) 1_455 ?
C1 C2 1.378(4) . ?
C2 C3 1.393(4) . ?
C2 C12 1.498(4) . ?
C3 C4 1.383(5) . ?
C4 C5 1.388(5) . ?
C4 C6 1.486(4) . ?
C6 C7 1.385(5) . ?
C6 C11 1.387(5) . ?
C7 C8 1.387(5) . ?
C8 C9 1.390(5) . ?
C9 C10 1.385(5) . ?
C9 C13 1.503(4) . ?
C10 C11 1.388(5) . ?
C14 C15 1.381(5) . ?
C15 C16 1.390(4) . ?
C15 C25 1.501(4) . ?
C16 C17 1.384(5) . ?
C17 C18 1.379(5) . ?
C17 C19 1.488(4) . ?
C19 C20 1.383(5) . ?
C19 C24 1.382(5) . ?
C20 C21 1.394(5) . ?
C21 C22 1.393(5) . ?
C22 C23 1.382(5) . ?
C22 C26 1.501(4) . ?
C23 C24 1.385(5) . ?
C27 C28 1.376(4) . ?
C28 C29 1.402(4) . ?
C28 C38 1.505(4) . ?
C29 C30 1.384(5) . ?
C30 C31 1.388(5) . ?
C30 C32 1.489(4) . ?
C32 C37 1.380(5) . ?
C32 C33 1.390(5) . ?
C33 C34 1.392(5) . ?
C34 C35 1.387(5) . ?
C35 C36 1.392(5) . ?
C35 C39 1.505(4) . ?
C36 C37 1.386(5) . ?
C40 C41 1.380(5) . ?
C41 C42 1.388(4) . ?
C41 C51 1.503(4) . ?
C42 C43 1.392(5) . ?
C43 C44 1.387(5) . ?
C43 C45 1.485(4) . ?
C45 C46 1.384(5) . ?
C45 C50 1.395(5) . ?
C46 C47 1.390(5) . ?
C47 C48 1.388(5) . ?
C48 C49 1.393(5) . ?
C48 C52 1.516(4) . ?
C49 C50 1.390(5) . ?

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 O2W 95.03(10) . . ?
O4 Co1 O1W 99.90(10) . . ?
O2W Co1 O1W 90.79(10) . . ?
O4 Co1 O10 94.41(9) . 2_255 ?
O2W Co1 O10 169.75(9) . 2_255 ?
O1W Co1 O10 91.52(9) . 2_255 ?
O4 Co1 N3 86.39(10) . 2_355 ?
O2W Co1 N3 86.02(10) . 2_355 ?
O1W Co1 N3 173.19(10) . 2_355 ?
O10 Co1 N3 90.60(9) 2_255 2_355 ?
O4 Co1 O5 173.70(9) . 2_556 ?
O2W Co1 O5 90.24(9) . 2_556 ?
O1W Co1 O5 83.44(9) . 2_556 ?
O10 Co1 O5 80.11(8) 2_255 2_556 ?
N3 Co1 O5 90.55(9) 2_355 2_556 ?
O16 Co2 O4W 95.50(11) 2_145 . ?
O16 Co2 O3W 97.39(10) 2_145 . ?
O4W Co2 O3W 91.21(10) . . ?
O16 Co2 O5 97.57(10) 2_145 1_455 ?
O4W Co2 O5 166.62(10) . 1_455 ?
O3W Co2 O5 89.92(9) . 1_455 ?
O16 Co2 N2 85.37(10) 2_145 . ?
O4W Co2 N2 86.42(10) . . ?
O3W Co2 N2 176.52(10) . . ?
O5 Co2 N2 91.81(9) 1_455 . ?
O16 Co2 O10 177.26(10) 2_145 1_756 ?
O4W Co2 O10 86.35(10) . 1_756 ?
O3W Co2 O10 84.57(9) . 1_756 ?
O5 Co2 O10 80.48(8) 1_455 1_756 ?
N2 Co2 O10 92.73(9) . 1_756 ?
O8 Co3 O5W 93.96(10) . . ?
O8 Co3 O6W 99.92(10) . . ?
O5W Co3 O6W 90.30(10) . . ?
O8 Co3 O1 95.25(9) . . ?
O5W Co3 O1 170.29(9) . . ?
O6W Co3 O1 91.15(9) . . ?
O8 Co3 N1 85.81(10) . 1_455 ?
O5W Co3 N1 86.34(10) . 1_455 ?
O6W Co3 N1 173.56(10) . 1_455 ?
O1 Co3 N1 91.26(9) . 1_455 ?
O8 Co3 O13 174.16(9) . . ?
O5W Co3 O13 90.46(9) . . ?
O6W Co3 O13 83.86(9) . . ?
O1 Co3 O13 80.15(8) . . ?
N1 Co3 O13 90.67(9) 1_455 . ?
O11 Co4 O8W 95.53(10) . . ?
O11 Co4 O7W 98.81(9) . . ?
O8W Co4 O7W 89.56(10) . . ?
O11 Co4 O13 94.34(9) . . ?
O8W Co4 O13 170.04(9) . . ?
O7W Co4 O13 90.29(9) . . ?
O11 Co4 N4 86.61(10) . 1_655 ?
O8W Co4 N4 87.19(10) . 1_655 ?
O7W Co4 N4 173.93(10) . 1_655 ?
O13 Co4 N4 92.03(9) . 1_655 ?
O11 Co4 O1 173.97(9) . . ?
O8W Co4 O1 90.08(9) . . ?
O7W Co4 O1 83.42(9) . . ?
O13 Co4 O1 80.01(8) . . ?
N4 Co4 O1 91.46(9) 1_655 . ?
C12 O1 Co3 123.8(2) . . ?
C12 O1 Co4 123.0(2) . . ?
Co3 O1 Co4 99.64(9) . . ?
C13 O4 Co1 132.8(2) . . ?
C25 O5 Co2 122.8(2) . 1_655 ?
C25 O5 Co1 123.4(2) . 2_556 ?
Co2 O5 Co1 99.45(9) 1_655 2_556 ?
C26 O8 Co3 134.7(2) . . ?
C38 O10 Co1 127.4(2) . 2_255 ?
C38 O10 Co2 121.4(2) . 1_354 ?
Co1 O10 Co2 99.94(9) 2_255 1_354 ?
C39 O11 Co4 130.9(2) . . ?
C51 O13 Co4 121.3(2) . . ?
C51 O13 Co3 123.7(2) . . ?
Co4 O13 Co3 100.20(9) . . ?
C52 O16 Co2 135.1(2) . 2_145 ?
C5 N1 C1 117.0(3) . . ?
C5 N1 Co3 122.3(2) . 1_655 ?
C1 N1 Co3 120.2(2) . 1_655 ?
C14 N2 C18 116.6(3) . . ?
C14 N2 Co2 120.0(2) . . ?
C18 N2 Co2 123.0(2) . . ?
C31 N3 C27 117.0(3) . . ?
C31 N3 Co1 120.4(2) . 2_355 ?
C27 N3 Co1 121.8(2) . 2_355 ?
C44 N4 C40 116.7(3) . . ?
C44 N4 Co4 123.9(2) . 1_455 ?
C40 N4 Co4 119.0(2) . 1_455 ?
N1 C1 C2 123.2(3) . . ?
C1 C2 C3 118.1(3) . . ?
C1 C2 C12 120.8(3) . . ?
C3 C2 C12 121.0(3) . . ?
C4 C3 C2 120.0(3) . . ?
C3 C4 C5 117.2(3) . . ?
C3 C4 C6 123.3(3) . . ?
C5 C4 C6 119.5(3) . . ?
N1 C5 C4 124.4(3) . . ?
C7 C6 C11 119.0(3) . . ?
C7 C6 C4 121.1(3) . . ?
C11 C6 C4 119.9(3) . . ?
C6 C7 C8 120.6(3) . . ?
C7 C8 C9 120.5(3) . . ?
C10 C9 C8 118.9(3) . . ?
C10 C9 C13 120.9(3) . . ?
C8 C9 C13 120.1(3) . . ?
C9 C10 C11 120.5(3) . . ?
C10 C11 C6 120.6(3) . . ?
O2 C12 O1 124.5(3) . . ?
O2 C12 C2 119.1(3) . . ?
O1 C12 C2 116.3(3) . . ?
O3 C13 O4 124.7(3) . . ?
O3 C13 C9 118.1(3) . . ?
O4 C13 C9 117.2(3) . . ?
N2 C14 C15 123.6(3) . . ?
C14 C15 C16 117.9(3) . . ?
C14 C15 C25 121.0(3) . . ?
C16 C15 C25 120.9(3) . . ?
C17 C16 C15 119.9(3) . . ?
C18 C17 C16 117.2(3) . . ?
C18 C17 C19 120.6(3) . . ?
C16 C17 C19 122.2(3) . . ?
N2 C18 C17 124.6(3) . . ?
C20 C19 C24 119.0(3) . . ?
C20 C19 C17 120.1(3) . . ?
C24 C19 C17 120.9(3) . . ?
C19 C20 C21 120.5(3) . . ?
C20 C21 C22 120.3(3) . . ?
C23 C22 C21 118.5(3) . . ?
C23 C22 C26 121.2(3) . . ?
C21 C22 C26 120.3(3) . . ?
C24 C23 C22 121.0(3) . . ?
C23 C24 C19 120.6(3) . . ?
O6 C25 O5 125.1(3) . . ?
O6 C25 C15 119.1(3) . . ?
O5 C25 C15 115.8(3) . . ?
O7 C26 O8 124.8(3) . . ?
O7 C26 C22 118.3(3) . . ?
O8 C26 C22 116.9(3) . . ?
N3 C27 C28 123.2(3) . . ?
C27 C28 C29 118.5(3) . . ?
C27 C28 C38 120.3(3) . . ?
C29 C28 C38 121.0(3) . . ?
C30 C29 C28 119.3(3) . . ?
C29 C30 C31 117.7(3) . . ?
C29 C30 C32 124.2(3) . . ?
C31 C30 C32 118.0(3) . . ?
N3 C31 C30 124.1(3) . . ?
C37 C32 C33 118.8(3) . . ?
C37 C32 C30 119.9(3) . . ?
C33 C32 C30 121.1(3) . . ?
C32 C33 C34 120.0(3) . . ?
C35 C34 C33 121.0(3) . . ?
C34 C35 C36 118.8(3) . . ?
C34 C35 C39 121.3(3) . . ?
C36 C35 C39 119.9(3) . . ?
C37 C36 C35 120.0(3) . . ?
C32 C37 C36 121.4(3) . . ?
O9 C38 O10 124.8(3) . . ?
O9 C38 C28 119.1(3) . . ?
O10 C38 C28 116.1(3) . . ?
O11 C39 O12 124.7(3) . . ?
O11 C39 C35 117.9(3) . . ?
O12 C39 C35 117.4(3) . . ?
N4 C40 C41 123.5(3) . . ?
C40 C41 C42 118.1(3) . . ?
C40 C41 C51 121.8(3) . . ?
C42 C41 C51 120.0(3) . . ?
C41 C42 C43 120.1(3) . . ?
C44 C43 C42 116.9(3) . . ?
C44 C43 C45 121.7(3) . . ?
C42 C43 C45 121.4(3) . . ?
N4 C44 C43 124.5(3) . . ?
C46 C45 C50 118.7(3) . . ?
C46 C45 C43 120.2(3) . . ?
C50 C45 C43 121.1(3) . . ?
C45 C46 C47 121.3(3) . . ?
C46 C47 C48 120.0(3) . . ?
C47 C48 C49 119.2(3) . . ?
C47 C48 C52 120.7(3) . . ?
C49 C48 C52 120.1(3) . . ?
C50 C49 C48 120.6(3) . . ?
C49 C50 C45 120.3(3) . . ?
O14 C51 O13 125.1(3) . . ?
O14 C51 C41 118.9(3) . . ?
O13 C51 C41 116.0(3) . . ?
O15 C52 O16 125.3(3) . . ?
O15 C52 C48 118.5(3) . . ?
O16 C52 C48 116.1(3) . . ?

_refine_diff_density_max         1.166
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.137

