# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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. 
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data_tcl6p28a
_database_code_depnum_ccdc_archive 'CCDC 1477417'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2016-07-18 downloaded from the CCDC.
;
_vrf_PLAT111_ALERT_2_B           
;
PROBLEM:  ADDSYM suggest that the correct space group is Cmcm           
RESPONSE: 
           trials to find a solution in this S.G. or lower symmetry
 S.G. in Ortho C were made.
 A possible solution was found,
 but efforts to refine the structure satisfactorily were unsuccesfull  
 (high R indices, the  ellipsoids getting non positive,
 the connectivity -bond lenght and  angles- was bad).
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H16 B Co F4 N4 Na O2'
_chemical_formula_sum            'C13 H16 B Co F4 N4 Na O2'
_chemical_formula_weight         429.03

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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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'
Na Na 0.0362 0.0249 '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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   9.991(3)
_cell_length_b                   6.986(2)
_cell_length_c                   12.879(4)
_cell_angle_alpha                90
_cell_angle_beta                 112.856(5)
_cell_angle_gamma                90
_cell_volume                     828.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    1727
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      26.90

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.720
_exptl_crystal_F_000             434
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.08
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_max          0.30
_exptl_absorpt_coefficient_mu    1.121
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.417707
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   'SADABS v2.10 BRUKER 21001'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3905
_diffrn_reflns_av_unetI/netI     0.0737
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.211
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_full        24.991
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             2514
_reflns_number_gt                1915
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.856
_reflns_Friedel_fraction_max     0.984
_reflns_Friedel_fraction_full    0.984

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.

1. Twinned data refinement
 Scales: 0.61(8) 0.39(8)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H12A,H12B,H12} of C12, {H7AA,H7AB,H7B} of C7, All C(H,H)
  groups
 At 1.5 times of:
  {H10D,H10E,H10F} of C10', {H10A,H10B,H10C} of C10
3. Rigid bond restraints
 C5, N1, C1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
C5 ∼ N1 ∼ C1: within 2A with sigma of 0.001 and sigma for terminal
atoms of 0.002
Uanis(N1) ∼ Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(N3') = Uanis(N3)
Uanis(C10) = Uanis(C10')
5. Rigid body (RIGU) restrains
 C6, C5, N1, C1, C13, N4, N2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N3, C8, C9, C10, C11, C7, N2, C12, N4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N3', C8', C9', C10', C11', C7, N2, C12, N4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: H7AA(0.5) H7AB(0.5) H7B(0.5) H12A(0.5) H12B(0.5) H12(0.5) N3(0.5)
 C8(0.5) H8A(0.5) H8B(0.5) C9(0.5) H9A(0.5) H9B(0.5) C10(0.5) H10A(0.5)
 H10B(0.5) H10C(0.5) C11(0.5) H11A(0.5) H11B(0.5) N3'(0.5) C8'(0.5) H8'(0.5)
 C9'(0.5) H9'A(0.5) H9'B(0.5) C10'(0.5) H10D(0.5) H10E(0.5) H10F(0.5) C11'(0.5)
 H11'(0.5)
7.a Secondary CH2 refined with riding coordinates:
 C7(H7AA,H7AB), C12(H12A,H12B), C8(H8A,H8B), C9(H9A,H9B), C11(H11A,H11B),
 C9'(H9'A,H9'B), C8'(H8'a, H8'b), C11'(H11', H11")
7.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), 
7.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C10'(H10D,H10E,H10F)
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] 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 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.40(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2514
_refine_ls_number_parameters     271
_refine_ls_number_restraints     145
_refine_ls_R_factor_all          0.1192
_refine_ls_R_factor_gt           0.0989
_refine_ls_wR_factor_ref         0.3121
_refine_ls_wR_factor_gt          0.2662
_refine_ls_goodness_of_fit_ref   1.264
_refine_ls_restrained_S_all      1.236
_refine_ls_shift/su_max          0.053
_refine_ls_shift/su_mean         0.007

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 0.60043(17) 0.0289(3) 0.20088(13) 0.0487(7) Uani 1 1 d . . . . .
Na1 Na -0.0009(10) 0.2807(13) -0.0010(8) 0.0350(10) Uani 1 1 d . . . . .
O0AA O 0.1744(8) 0.030(2) 0.0471(7) 0.0428(19) Uani 1 1 d . . . . .
N1 N 0.5246(10) 0.025(3) 0.0493(8) 0.0421(15) Uani 1 1 d . U . . .
F1 F -0.2726(10) 0.028(2) -0.3199(7) 0.071(2) Uani 1 1 d . . . . .
C1 C 0.6163(12) 0.031(4) -0.0052(10) 0.0418(15) Uani 1 1 d . U . . .
B1 B -0.1246(17) 0.021(4) -0.2505(12) 0.049(3) Uani 1 1 d . . . . .
O2 O 0.8733(9) 0.037(2) 0.0467(7) 0.0426(19) Uani 1 1 d . . . . .
N2 N 0.4060(9) 0.031(2) 0.1841(8) 0.0366(19) Uani 1 1 d . U . . .
F2 F -0.0464(10) 0.030(2) -0.3211(7) 0.071(2) Uani 1 1 d . . . . .
C2 C 0.5625(14) 0.028(3) -0.1190(11) 0.048(3) Uani 1 1 d . . . . .
H2 H 0.6262 0.0277 -0.1579 0.057 Uiso 1 1 calc R U . . .
F3 F -0.0915(16) 0.1891(16) -0.1866(9) 0.080(6) Uani 1 1 d . . . . .
C3 C 0.4117(13) 0.027(4) -0.1792(11) 0.045(3) Uani 1 1 d . . . . .
H3 H 0.3733 0.0196 -0.2591 0.054 Uiso 1 1 calc R U . . .
N4 N 0.7771(10) 0.022(3) 0.1847(8) 0.037(2) Uani 1 1 d . U . . .
C4 C 0.3156(13) 0.035(3) -0.1218(11) 0.046(3) Uani 1 1 d . . . . .
H4 H 0.2132 0.0419 -0.1611 0.056 Uiso 1 1 calc R U . . .
F4 F -0.0917(13) -0.1339(16) -0.1841(11) 0.070(4) Uani 1 1 d . . . . .
C5 C 0.3810(12) 0.034(3) -0.0040(10) 0.0422(16) Uani 1 1 d . U . . .
C6 C 0.3075(11) 0.028(3) 0.0788(9) 0.035(2) Uani 1 1 d . U . . .
C7 C 0.3728(14) 0.029(4) 0.2834(11) 0.053(3) Uani 1 1 d . U . . .
H7AA H 0.2903 -0.0566 0.2743 0.064 Uiso 0.5 1 calc R U P A 1
H7AB H 0.3507 0.1596 0.3026 0.064 Uiso 0.5 1 calc R U P A 1
H7BA H 0.2978 0.1287 0.2721 0.064 Uiso 0.5 1 calc R U P B 2
H7BB H 0.3262 -0.0953 0.2843 0.064 Uiso 0.5 1 calc R U P B 2
C12 C 0.9131(12) 0.033(5) 0.2838(10) 0.055(3) Uani 1 1 d . U . . .
H12A H 0.9835 0.1214 0.2720 0.066 Uiso 0.5 1 calc R U P C 1
H12B H 0.9582 -0.0942 0.3065 0.066 Uiso 0.5 1 calc R U P C 1
H12C H 0.9711 -0.0802 0.2813 0.066 Uiso 0.5 1 calc R U P D 2
H12D H 0.9661 0.1467 0.2734 0.066 Uiso 0.5 1 calc R U P D 2
C13 C 0.7706(11) 0.032(3) 0.0793(9) 0.033(2) Uani 1 1 d . U . . .
N3 N 0.649(3) 0.044(5) 0.364(2) 0.044(3) Uani 0.5 1 d . U P E 1
C8 C 0.528(4) -0.054(5) 0.380(3) 0.059(7) Uani 0.5 1 d . U P E 1
H8A H 0.5317 -0.0287 0.4567 0.071 Uiso 0.5 1 calc R U P E 1
H8B H 0.5352 -0.1937 0.3710 0.071 Uiso 0.5 1 calc R U P E 1
C9 C 0.782(3) -0.047(4) 0.418(3) 0.044(5) Uani 0.5 1 d . U P E 1
H9A H 0.7879 -0.1751 0.3875 0.053 Uiso 0.5 1 calc R U P E 1
H9B H 0.8154 -0.0504 0.5013 0.053 Uiso 0.5 1 calc R U P E 1
C10 C 0.648(4) 0.245(4) 0.411(3) 0.045(4) Uani 0.5 1 d . U P E 1
H10A H 0.7237 0.3231 0.4005 0.067 Uiso 0.5 1 calc R U P E 1
H10B H 0.6670 0.2375 0.4913 0.067 Uiso 0.5 1 calc R U P E 1
H10C H 0.5531 0.3046 0.3705 0.067 Uiso 0.5 1 calc R U P E 1
C11 C 0.851(4) 0.117(4) 0.373(3) 0.045(5) Uani 0.5 1 d . U P E 1
H11A H 0.9313 0.1778 0.4365 0.054 Uiso 0.5 1 calc R U P E 1
H11B H 0.7773 0.2166 0.3359 0.054 Uiso 0.5 1 calc R U P E 1
N3' N 0.710(3) 0.040(6) 0.359(2) 0.044(3) Uani 0.5 1 d . U P E 2
C8' C 0.477(3) 0.057(6) 0.390(2) 0.048(7) Uani 0.5 1 d . U P E 2
H8'A H 0.4367 0.0123 0.4448 0.058 Uiso 0.5 1 calc R U P E 2
H8'B H 0.4948 0.1958 0.4016 0.058 Uiso 0.5 1 calc R U P E 2
C9' C 0.631(4) -0.048(4) 0.419(3) 0.047(5) Uani 0.5 1 d . U P E 2
H9'A H 0.6893 -0.0401 0.5011 0.056 Uiso 0.5 1 calc R U P E 2
H9'B H 0.6151 -0.1848 0.3980 0.056 Uiso 0.5 1 calc R U P E 2
C10' C 0.762(3) 0.240(4) 0.415(3) 0.045(4) Uani 0.5 1 d . U P E 2
H10D H 0.8567 0.2705 0.4137 0.067 Uiso 0.5 1 calc R U P E 2
H10E H 0.7692 0.2377 0.4932 0.067 Uiso 0.5 1 calc R U P E 2
H10F H 0.6912 0.3383 0.3730 0.067 Uiso 0.5 1 calc R U P E 2
C11' C 0.917(3) 0.044(8) 0.395(2) 0.050(5) Uani 0.5 1 d . U P E 2
H11' H 0.9626 0.1639 0.4332 0.060 Uiso 0.5 1 calc R U P E 2
H11" H 0.9668 -0.0674 0.4411 0.060 Uiso 0.5 1 calc R U P E 2


_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 1.799(10) . ?
Co1 N4 1.857(8) . ?
Co1 N2 1.870(8) . ?
Co1 N3' 1.91(3) . ?
Co1 N3 1.97(3) . ?
Na1 F4 2.276(16) 2 ?
Na1 F3 2.295(15) . ?
Na1 O2 2.336(15) 1_455 ?
Na1 O0AA 2.363(15) 2 ?
Na1 O0AA 2.384(16) . ?
Na1 O2 2.401(15) 2_655 ?
Na1 Na1 3.4933(11) 2 ?
Na1 Na1 3.4933(11) 2_545 ?
O0AA C6 1.231(13) . ?
O0AA Na1 2.363(15) 2_545 ?
N1 C5 1.330(16) . ?
N1 C1 1.354(13) . ?
F1 B1 1.401(18) . ?
C1 C2 1.351(19) . ?
C1 C13 1.502(15) . ?
B1 F4 1.34(3) . ?
B1 F3 1.40(2) . ?
B1 F2 1.411(17) . ?
O2 C13 1.251(12) . ?
O2 Na1 2.336(15) 1_655 ?
O2 Na1 2.401(15) 2_645 ?
N2 C6 1.331(14) . ?
N2 C7 1.440(14) . ?
C2 C3 1.401(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.422(15) . ?
C3 H3 0.9500 . ?
N4 C13 1.336(15) . ?
N4 C12 1.461(15) . ?
C4 C5 1.400(18) . ?
C4 H4 0.9500 . ?
F4 Na1 2.276(16) 2_545 ?
C5 C6 1.512(14) . ?
C7 C8' 1.37(3) . ?
C7 C8 1.67(5) . ?
C7 H7AA 0.9900 . ?
C7 H7AB 0.9900 . ?
C7 H7BA 0.9900 . ?
C7 H7BB 0.9900 . ?
C12 C11' 1.42(3) . ?
C12 C11 1.61(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 H12C 0.9900 . ?
C12 H12D 0.9900 . ?
N3 C9 1.39(4) . ?
N3 C8 1.47(4) . ?
N3 C10 1.53(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C11 1.57(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
N3' C9' 1.43(4) . ?
N3' C10' 1.57(5) . ?
N3' C11' 1.93(4) . ?
C8' C9' 1.61(4) . ?
C8' H8'A 0.9900 . ?
C8' H8'B 0.9900 . ?
C9' H9'A 0.9900 . ?
C9' H9'B 0.9900 . ?
C10' H10D 0.9800 . ?
C10' H10E 0.9800 . ?
C10' H10F 0.9800 . ?
C11' H11' 0.9900 . ?
C11' H11" 0.9900 . ?

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 N4 84.0(4) . . ?
N1 Co1 N2 83.9(4) . . ?
N4 Co1 N2 167.9(4) . . ?
N1 Co1 N3' 170.8(8) . . ?
N4 Co1 N3' 86.9(7) . . ?
N2 Co1 N3' 105.2(7) . . ?
N1 Co1 N3 170.2(8) . . ?
N4 Co1 N3 105.6(7) . . ?
N2 Co1 N3 86.4(7) . . ?
F4 Na1 F3 178.8(8) 2 . ?
F4 Na1 O2 87.5(5) 2 1_455 ?
F3 Na1 O2 92.1(6) . 1_455 ?
F4 Na1 O0AA 91.8(5) 2 2 ?
F3 Na1 O0AA 89.4(5) . 2 ?
O2 Na1 O0AA 100.7(5) 1_455 2 ?
F4 Na1 O0AA 87.8(5) 2 . ?
F3 Na1 O0AA 91.0(6) . . ?
O2 Na1 O0AA 79.2(5) 1_455 . ?
O0AA Na1 O0AA 179.6(5) 2 . ?
F4 Na1 O2 91.3(5) 2 2_655 ?
F3 Na1 O2 89.1(5) . 2_655 ?
O2 Na1 O2 178.4(6) 1_455 2_655 ?
O0AA Na1 O2 78.3(5) 2 2_655 ?
O0AA Na1 O2 101.9(5) . 2_655 ?
F4 Na1 Na1 74.4(5) 2 2 ?
F3 Na1 Na1 106.6(5) . 2 ?
O2 Na1 Na1 136.8(5) 1_455 2 ?
O0AA Na1 Na1 42.8(4) 2 2 ?
O0AA Na1 Na1 137.1(6) . 2 ?
O2 Na1 Na1 41.8(3) 2_655 2 ?
F4 Na1 Na1 104.8(5) 2 2_545 ?
F3 Na1 Na1 74.2(5) . 2_545 ?
O2 Na1 Na1 43.2(3) 1_455 2_545 ?
O0AA Na1 Na1 137.7(6) 2 2_545 ?
O0AA Na1 Na1 42.4(3) . 2_545 ?
O2 Na1 Na1 138.2(5) 2_655 2_545 ?
Na1 Na1 Na1 179.2(7) 2 2_545 ?
C6 O0AA Na1 131.9(13) . 2_545 ?
C6 O0AA Na1 133.2(13) . . ?
Na1 O0AA Na1 94.8(3) 2_545 . ?
C5 N1 C1 122.9(11) . . ?
C5 N1 Co1 118.3(7) . . ?
C1 N1 Co1 118.5(8) . . ?
C2 C1 N1 119.8(11) . . ?
C2 C1 C13 130.6(9) . . ?
N1 C1 C13 109.6(10) . . ?
F4 B1 F3 111.1(11) . . ?
F4 B1 F1 112.0(17) . . ?
F3 B1 F1 107.0(17) . . ?
F4 B1 F2 112.9(17) . . ?
F3 B1 F2 106.0(17) . . ?
F1 B1 F2 107.4(12) . . ?
C13 O2 Na1 134.7(11) . 1_655 ?
C13 O2 Na1 130.2(11) . 2_645 ?
Na1 O2 Na1 95.0(3) 1_655 2_645 ?
C6 N2 C7 124.8(9) . . ?
C6 N2 Co1 116.2(6) . . ?
C7 N2 Co1 119.0(8) . . ?
C1 C2 C3 119.3(10) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
B1 F3 Na1 139.0(12) . . ?
C2 C3 C4 120.7(11) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.6 . . ?
C13 N4 C12 123.2(9) . . ?
C13 N4 Co1 116.1(8) . . ?
C12 N4 Co1 120.2(8) . . ?
C5 C4 C3 115.9(11) . . ?
C5 C4 H4 122.0 . . ?
C3 C4 H4 122.0 . . ?
B1 F4 Na1 141.3(12) . 2_545 ?
N1 C5 C4 121.0(9) . . ?
N1 C5 C6 110.9(10) . . ?
C4 C5 C6 127.9(10) . . ?
O0AA C6 N2 127.9(9) . . ?
O0AA C6 C5 121.6(11) . . ?
N2 C6 C5 110.5(9) . . ?
C8' C7 N2 122.6(15) . . ?
N2 C7 C8 101.3(16) . . ?
N2 C7 H7AA 111.5 . . ?
C8 C7 H7AA 111.5 . . ?
N2 C7 H7AB 111.5 . . ?
C8 C7 H7AB 111.5 . . ?
H7AA C7 H7AB 109.3 . . ?
C8' C7 H7BA 106.7 . . ?
N2 C7 H7BA 106.7 . . ?
C8' C7 H7BB 106.7 . . ?
N2 C7 H7BB 106.7 . . ?
H7BA C7 H7BB 106.6 . . ?
C11' C12 N4 122.3(15) . . ?
N4 C12 C11 99.0(14) . . ?
N4 C12 H12A 111.9 . . ?
C11 C12 H12A 111.9 . . ?
N4 C12 H12B 112.0 . . ?
C11 C12 H12B 112.0 . . ?
H12A C12 H12B 109.6 . . ?
C11' C12 H12C 106.8 . . ?
N4 C12 H12C 106.8 . . ?
C11' C12 H12D 106.7 . . ?
N4 C12 H12D 106.7 . . ?
H12C C12 H12D 106.6 . . ?
O2 C13 N4 128.3(10) . . ?
O2 C13 C1 120.1(9) . . ?
N4 C13 C1 111.6(8) . . ?
C9 N3 C8 113(3) . . ?
C9 N3 C10 112(2) . . ?
C8 N3 C10 104(3) . . ?
C9 N3 Co1 108(2) . . ?
C8 N3 Co1 104(2) . . ?
C10 N3 Co1 115(2) . . ?
N3 C8 C7 108(3) . . ?
N3 C8 H8A 110.1 . . ?
C7 C8 H8A 110.1 . . ?
N3 C8 H8B 110.0 . . ?
C7 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
N3 C9 C11 87(3) . . ?
N3 C9 H9A 114.1 . . ?
C11 C9 H9A 114.1 . . ?
N3 C9 H9B 114.1 . . ?
C11 C9 H9B 114.1 . . ?
H9A C9 H9B 111.3 . . ?
N3 C10 H10A 109.4 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 C12 110(2) . . ?
C9 C11 H11A 109.6 . . ?
C12 C11 H11A 109.6 . . ?
C9 C11 H11B 109.6 . . ?
C12 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C9' N3' C10' 107(2) . . ?
C9' N3' Co1 110(2) . . ?
C10' N3' Co1 118(2) . . ?
C9' N3' C11' 130(3) . . ?
C10' N3' C11' 75(2) . . ?
Co1 N3' C11' 111.7(13) . . ?
C7 C8' C9' 117(2) . . ?
C7 C8' H8'A 108.0 . . ?
C9' C8' H8'A 108.1 . . ?
C7 C8' H8'B 108.0 . . ?
C9' C8' H8'B 108.0 . . ?
H8'A C8' H8'B 107.3 . . ?
N3' C9' C8' 111(3) . . ?
N3' C9' H9'A 109.5 . . ?
C8' C9' H9'A 109.5 . . ?
N3' C9' H9'B 109.5 . . ?
C8' C9' H9'B 109.5 . . ?
H9'A C9' H9'B 108.1 . . ?
N3' C10' H10D 109.5 . . ?
N3' C10' H10E 109.5 . . ?
H10D C10' H10E 109.5 . . ?
N3' C10' H10F 109.5 . . ?
H10D C10' H10F 109.5 . . ?
H10E C10' H10F 109.5 . . ?
C12 C11' N3' 98.9(18) . . ?
C12 C11' H11' 112.1 . . ?
N3' C11' H11' 112.0 . . ?
C12 C11' H11" 111.9 . . ?
N3' C11' H11" 112.0 . . ?
H11' C11' H11" 109.7 . . ?

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
N4 Co1 N1 C5 -177.6(19) . . . . ?
N2 Co1 N1 C5 3.2(18) . . . . ?
N4 Co1 N1 C1 -3.9(18) . . . . ?
N2 Co1 N1 C1 176.9(18) . . . . ?
C5 N1 C1 C2 -6(4) . . . . ?
Co1 N1 C1 C2 -179.8(18) . . . . ?
C5 N1 C1 C13 176(2) . . . . ?
Co1 N1 C1 C13 2(2) . . . . ?
N1 Co1 N2 C6 0.1(15) . . . . ?
N4 Co1 N2 C6 -4(5) . . . . ?
N3' Co1 N2 C6 178.6(18) . . . . ?
N3 Co1 N2 C6 178.1(17) . . . . ?
N1 Co1 N2 C7 178.4(19) . . . . ?
N4 Co1 N2 C7 174(4) . . . . ?
N3' Co1 N2 C7 -3(2) . . . . ?
N3 Co1 N2 C7 -4(2) . . . . ?
N1 C1 C2 C3 2(4) . . . . ?
C13 C1 C2 C3 180(2) . . . . ?
F4 B1 F3 Na1 -1(2) . . . . ?
F1 B1 F3 Na1 121.1(16) . . . . ?
F2 B1 F3 Na1 -124.5(16) . . . . ?
C1 C2 C3 C4 3(4) . . . . ?
N1 Co1 N4 C13 4.8(15) . . . . ?
N2 Co1 N4 C13 9(5) . . . . ?
N3' Co1 N4 C13 -173.6(17) . . . . ?
N3 Co1 N4 C13 -173.3(16) . . . . ?
N1 Co1 N4 C12 177(2) . . . . ?
N2 Co1 N4 C12 -179(3) . . . . ?
N3' Co1 N4 C12 -2(2) . . . . ?
N3 Co1 N4 C12 -2(2) . . . . ?
C2 C3 C4 C5 -4(3) . . . . ?
F3 B1 F4 Na1 0(2) . . . 2_545 ?
F1 B1 F4 Na1 -119.4(16) . . . 2_545 ?
F2 B1 F4 Na1 119.2(16) . . . 2_545 ?
C1 N1 C5 C4 5(4) . . . . ?
Co1 N1 C5 C4 178.6(16) . . . . ?
C1 N1 C5 C6 -178.8(18) . . . . ?
Co1 N1 C5 C6 -5(3) . . . . ?
C3 C4 C5 N1 0(3) . . . . ?
C3 C4 C5 C6 -175(2) . . . . ?
Na1 O0AA C6 N2 -94(2) 2_545 . . . ?
Na1 O0AA C6 N2 91(2) . . . . ?
Na1 O0AA C6 C5 90(2) 2_545 . . . ?
Na1 O0AA C6 C5 -85.1(19) . . . . ?
C7 N2 C6 O0AA 2(4) . . . . ?
Co1 N2 C6 O0AA -179.4(17) . . . . ?
C7 N2 C6 C5 179(2) . . . . ?
Co1 N2 C6 C5 -3(2) . . . . ?
N1 C5 C6 O0AA -178.1(19) . . . . ?
C4 C5 C6 O0AA -2(3) . . . . ?
N1 C5 C6 N2 5(2) . . . . ?
C4 C5 C6 N2 -179(2) . . . . ?
C6 N2 C7 C8' -172(3) . . . . ?
Co1 N2 C7 C8' 10(4) . . . . ?
C6 N2 C7 C8 158(2) . . . . ?
Co1 N2 C7 C8 -20(3) . . . . ?
C13 N4 C12 C11' 173(3) . . . . ?
Co1 N4 C12 C11' 2(4) . . . . ?
C13 N4 C12 C11 153.3(19) . . . . ?
Co1 N4 C12 C11 -18(3) . . . . ?
Na1 O2 C13 N4 -95(2) 1_655 . . . ?
Na1 O2 C13 N4 89(2) 2_645 . . . ?
Na1 O2 C13 C1 87.0(19) 1_655 . . . ?
Na1 O2 C13 C1 -88.8(19) 2_645 . . . ?
C12 N4 C13 O2 6(3) . . . . ?
Co1 N4 C13 O2 177.4(15) . . . . ?
C12 N4 C13 C1 -176(2) . . . . ?
Co1 N4 C13 C1 -5(2) . . . . ?
C2 C1 C13 O2 2(4) . . . . ?
N1 C1 C13 O2 179.8(18) . . . . ?
C2 C1 C13 N4 -176(2) . . . . ?
N1 C1 C13 N4 2(2) . . . . ?
C9 N3 C8 C7 -164(2) . . . . ?
C10 N3 C8 C7 74(3) . . . . ?
Co1 N3 C8 C7 -47(3) . . . . ?
N2 C7 C8 N3 44(3) . . . . ?
C8 N3 C9 C11 -179(3) . . . . ?
C10 N3 C9 C11 -62(3) . . . . ?
Co1 N3 C9 C11 66(2) . . . . ?
N3 C9 C11 C12 -114(2) . . . . ?
N4 C12 C11 C9 80(3) . . . . ?
N2 C7 C8' C9' -41(5) . . . . ?
C10' N3' C9' C8' 71(3) . . . . ?
Co1 N3' C9' C8' -59(3) . . . . ?
C11' N3' C9' C8' 156(3) . . . . ?
C7 C8' C9' N3' 71(4) . . . . ?
N4 C12 C11' N3' 0(4) . . . . ?

_refine_diff_density_max         1.828
_refine_diff_density_min         -1.722
_refine_diff_density_rms         0.195



####################################################################### 
# 
# 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_tcl3p50violet
_database_code_depnum_ccdc_archive 'CCDC 1477418'
_audit_update_record             
;
2016-07-08 deposited with the CCDC.
2016-07-18 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         'C18 H23 Co N4 O4, H2 O'
_chemical_formula_sum            'C18 H25 Co N4 O5'
_chemical_formula_weight         436.35

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      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                   8.001(15)
_cell_length_b                   9.657(19)
_cell_length_c                   12.97(2)
_cell_angle_alpha                92.10(3)
_cell_angle_beta                 102.94(3)
_cell_angle_gamma                105.15(3)
_cell_volume                     938(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1218
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      24.49

_exptl_crystal_description       plate
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.08
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_max          0.20
_exptl_absorpt_coefficient_mu    0.954
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.298558
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   'SADABS v2.10 BRUKER 2001'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5488
_diffrn_reflns_av_unetI/netI     0.1313
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.619
_diffrn_reflns_theta_max         28.389
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.859
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.859
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.859
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             4040
_reflns_number_gt                2798
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 OH2 Hydrogens were located from the difference Fourier Map
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0861P)²] 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         4040
_refine_ls_number_parameters     305
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1047
_refine_ls_R_factor_gt           0.0730
_refine_ls_wR_factor_ref         0.1980
_refine_ls_wR_factor_gt          0.1763
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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 0.87981(8) 0.28109(7) 0.20379(5) 0.0233(2) Uani 1 1 d . . . . .
O1 O 1.3025(5) 0.5544(4) 0.4051(3) 0.0313(8) Uani 1 1 d . . . . .
O2 O 0.7141(5) -0.1356(4) 0.2584(3) 0.0347(9) Uani 1 1 d . . . . .
O3 O 0.7482(5) 0.3554(4) 0.0873(3) 0.0314(8) Uani 1 1 d . . . . .
O4 O 1.0380(4) 0.2392(4) 0.1236(3) 0.0247(7) Uani 1 1 d . . . . .
N1 N 1.0219(5) 0.2078(4) 0.3091(3) 0.0211(8) Uani 1 1 d . . . . .
N2 N 1.0437(5) 0.4615(4) 0.2709(3) 0.0250(9) Uani 1 1 d . . . . .
N3 N 0.7315(12) 0.3646(10) 0.2796(7) 0.021(2) Uani 0.517(10) 1 d D . P A 1
N3' N 0.6893(12) 0.2872(11) 0.2811(7) 0.021(2) Uani 0.483(10) 1 d D . P A 2
N4 N 0.7323(5) 0.0841(5) 0.1830(3) 0.0282(10) Uani 1 1 d . . . . .
C1 C 0.9786(6) 0.0630(5) 0.3139(4) 0.0231(10) Uani 1 1 d . . . . .
C2 C 1.0946(7) 0.0035(6) 0.3827(4) 0.0289(11) Uani 1 1 d . . . . .
H2A H 1.0672 -0.0955 0.3867 0.035 Uiso 1 1 calc R U . . .
C3 C 1.2512(7) 0.0942(5) 0.4451(4) 0.0253(11) Uani 1 1 d . . . . .
H3A H 1.3296 0.0562 0.4921 0.030 Uiso 1 1 calc R U . . .
C4 C 1.2921(6) 0.2432(5) 0.4375(4) 0.0225(10) Uani 1 1 d . . . . .
H4A H 1.3963 0.3048 0.4801 0.027 Uiso 1 1 calc R U . . .
C5 C 1.1749(6) 0.2977(5) 0.3656(4) 0.0224(10) Uani 1 1 d . . . . .
C6 C 1.1832(7) 0.4538(5) 0.3487(4) 0.0241(10) Uani 1 1 d . . . . .
C8 C 0.9740(7) 0.5874(6) 0.2777(5) 0.0318(12) Uani 1 1 d . . . . .
H8A H 0.9885 0.6433 0.2181 0.038 Uiso 0.517(10) 1 d R U P A 1
H8B H 1.0360 0.6489 0.3433 0.038 Uiso 0.517(10) 1 d R U P A 1
H8C H 0.9340 0.6124 0.2073 0.038 Uiso 0.483(10) 1 d R U P A 2
H8D H 1.0694 0.6675 0.3162 0.038 Uiso 0.483(10) 1 d R U P A 2
C9 C 0.7769(14) 0.5238(10) 0.2737(9) 0.022(2) Uani 0.517(10) 1 d D . P A 1
H9A H 0.7476 0.5694 0.3325 0.026 Uiso 0.517(10) 1 calc R U P A 1
H9B H 0.7056 0.5441 0.2081 0.026 Uiso 0.517(10) 1 calc R U P A 1
C10 C 0.7683(14) 0.3406(14) 0.3951(8) 0.031(3) Uani 0.517(10) 1 d . . P A 1
H10A H 0.6896 0.3762 0.4282 0.046 Uiso 0.517(10) 1 calc R U P A 1
H10B H 0.8898 0.3909 0.4293 0.046 Uiso 0.517(10) 1 calc R U P A 1
H10C H 0.7491 0.2394 0.4019 0.046 Uiso 0.517(10) 1 calc R U P A 1
C11 C 0.5347(11) 0.3066(10) 0.2307(7) 0.020(2) Uani 0.517(10) 1 d . . P A 1
H11A H 0.5087 0.3403 0.1609 0.024 Uiso 0.517(10) 1 calc R U P A 1
H11B H 0.4708 0.3464 0.2740 0.024 Uiso 0.517(10) 1 calc R U P A 1
C12 C 0.4619(15) 0.1387(12) 0.2187(10) 0.026(3) Uani 0.517(10) 1 d . . P A 1
H12A H 0.4857 0.1050 0.2886 0.031 Uiso 0.517(10) 1 calc R U P A 1
H12B H 0.3335 0.1126 0.1912 0.031 Uiso 0.517(10) 1 calc R U P A 1
C9' C 0.8250(15) 0.5600(11) 0.3307(11) 0.027(3) Uani 0.483(10) 1 d D . P A 2
H9'A H 0.7865 0.6471 0.3327 0.032 Uiso 0.483(10) 1 calc R U P A 2
H9'B H 0.8714 0.5444 0.4038 0.032 Uiso 0.483(10) 1 calc R U P A 2
C10' C 0.7337(15) 0.2486(13) 0.3919(7) 0.017(2) Uani 0.483(10) 1 d . . P A 2
H10D H 0.6428 0.2584 0.4267 0.026 Uiso 0.483(10) 1 calc R U P A 2
H10E H 0.8466 0.3119 0.4298 0.026 Uiso 0.483(10) 1 calc R U P A 2
H10F H 0.7403 0.1508 0.3907 0.026 Uiso 0.483(10) 1 calc R U P A 2
C11' C 0.6590(14) 0.4337(12) 0.2833(8) 0.026(3) Uani 0.483(10) 1 d D . P A 2
H11C H 0.5709 0.4340 0.3239 0.031 Uiso 0.483(10) 1 calc R U P A 2
H11D H 0.6087 0.4504 0.2111 0.031 Uiso 0.483(10) 1 calc R U P A 2
C12' C 0.5138(17) 0.1816(15) 0.2216(12) 0.0293(11) Uani 0.483(10) 1 d D . P A 2
H12C H 0.4402 0.2343 0.1792 0.035 Uiso 0.483(10) 1 calc R U P A 2
H12D H 0.4509 0.1363 0.2728 0.035 Uiso 0.483(10) 1 calc R U P A 2
C13 C 0.5396(6) 0.0618(6) 0.1474(4) 0.0293(11) Uani 1 1 d . . . . .
H13A H 0.4812 -0.0408 0.1406 0.035 Uiso 0.517(10) 1 d R U P A 1
H13B H 0.5134 0.0948 0.0773 0.035 Uiso 0.517(10) 1 d R U P A 1
H13C H 0.4743 -0.0328 0.1583 0.035 Uiso 0.483(10) 1 d R U P A 2
H13D H 0.5052 0.0771 0.0738 0.035 Uiso 0.483(10) 1 d R U P A 2
C14 C 0.7934(6) -0.0085(5) 0.2467(4) 0.0261(11) Uani 1 1 d . . . . .
C16 C 0.6290(7) 0.3983(6) -0.0879(4) 0.0309(12) Uani 1 1 d . . . . .
H16A H 0.5899 0.4670 -0.0508 0.046 Uiso 1 1 calc R U . . .
H16B H 0.5275 0.3215 -0.1244 0.046 Uiso 1 1 calc R U . . .
H16C H 0.6899 0.4450 -0.1385 0.046 Uiso 1 1 calc R U . . .
C17 C 0.7552(6) 0.3371(5) -0.0086(4) 0.0233(10) Uani 1 1 d . . . . .
C18 C 0.8651(7) 0.2673(6) -0.0435(4) 0.0306(12) Uani 1 1 d . . . . .
H18A H 0.8436 0.2428 -0.1163 0.037 Uiso 1 1 calc R U . . .
C19 C 1.0056(6) 0.2313(5) 0.0230(4) 0.0238(10) Uani 1 1 d . . . . .
C20 C 1.1350(7) 0.1764(6) -0.0247(4) 0.0349(13) Uani 1 1 d . . . . .
H20A H 1.1501 0.0899 0.0055 0.052 Uiso 1 1 calc R U . . .
H20B H 1.2481 0.2483 -0.0096 0.052 Uiso 1 1 calc R U . . .
H20C H 1.0890 0.1561 -0.1003 0.052 Uiso 1 1 calc R U . . .
O1W O 0.4034(6) 0.8320(5) 0.3399(4) 0.0377(10) Uani 1 1 d . . . . .
H1W H 0.471(9) 0.815(7) 0.316(5) 0.04(2) Uiso 1 1 d . . . . .
H2W H 0.369(12) 0.772(10) 0.371(7) 0.09(3) 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 N1 1.859(4) . ?
Co1 O3 1.915(4) . ?
Co1 O4 1.917(4) . ?
Co1 N2 1.923(5) . ?
Co1 N4 1.931(5) . ?
Co1 N3 1.997(10) . ?
Co1 N3' 2.014(10) . ?
O1 C6 1.241(6) . ?
O2 C14 1.258(6) . ?
O3 C17 1.266(6) . ?
O4 C19 1.267(6) . ?
N1 C5 1.336(6) . ?
N1 C1 1.358(7) . ?
N2 C6 1.347(6) . ?
N2 C8 1.471(6) . ?
N3 C9 1.493(12) . ?
N3 C10 1.500(14) . ?
N3 C11 1.504(12) . ?
N3' C10' 1.487(13) . ?
N3' C11' 1.498(14) . ?
N3' C12' 1.522(13) . ?
N4 C14 1.351(7) . ?
N4 C13 1.462(6) . ?
C1 C2 1.390(7) . ?
C1 C14 1.508(7) . ?
C2 C3 1.383(7) . ?
C2 H2A 0.9300 . ?
C3 C4 1.402(7) . ?
C3 H3A 0.9300 . ?
C4 C5 1.389(6) . ?
C4 H4A 0.9300 . ?
C5 C6 1.517(7) . ?
C8 C9' 1.477(13) . ?
C8 C9 1.524(12) . ?
C8 H8A 0.9699 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9601 . ?
C8 H8D 0.9600 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.562(14) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.496(13) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C9' C11' 1.537(12) . ?
C9' H9'A 0.9700 . ?
C9' H9'B 0.9700 . ?
C10' H10D 0.9600 . ?
C10' H10E 0.9600 . ?
C10' H10F 0.9600 . ?
C11' H11C 0.9700 . ?
C11' H11D 0.9700 . ?
C12' C13 1.562(16) . ?
C12' H12C 0.9700 . ?
C12' H12D 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9600 . ?
C13 H13D 0.9601 . ?
C16 C17 1.522(6) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.377(7) . ?
C18 C19 1.386(7) . ?
C18 H18A 0.9300 . ?
C19 C20 1.512(7) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
O1W H1W 0.73(7) . ?
O1W H2W 0.75(10) . ?

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 O3 174.74(16) . . ?
N1 Co1 O4 81.46(19) . . ?
O3 Co1 O4 93.32(19) . . ?
N1 Co1 N2 82.2(2) . . ?
O3 Co1 N2 97.6(2) . . ?
O4 Co1 N2 93.9(2) . . ?
N1 Co1 N4 82.0(2) . . ?
O3 Co1 N4 99.0(2) . . ?
O4 Co1 N4 93.32(19) . . ?
N2 Co1 N4 161.44(17) . . ?
N1 Co1 N3 104.6(3) . . ?
O3 Co1 N3 80.4(3) . . ?
O4 Co1 N3 168.5(3) . . ?
N2 Co1 N3 77.6(3) . . ?
N4 Co1 N3 97.1(3) . . ?
N1 Co1 N3' 97.2(3) . . ?
O3 Co1 N3' 88.0(3) . . ?
O4 Co1 N3' 169.6(3) . . ?
N2 Co1 N3' 96.1(3) . . ?
N4 Co1 N3' 76.3(3) . . ?
C17 O3 Co1 124.8(3) . . ?
C19 O4 Co1 123.6(3) . . ?
C5 N1 C1 123.2(4) . . ?
C5 N1 Co1 117.9(3) . . ?
C1 N1 Co1 118.2(3) . . ?
C6 N2 C8 118.0(4) . . ?
C6 N2 Co1 116.4(3) . . ?
C8 N2 Co1 118.3(3) . . ?
C9 N3 C10 107.2(8) . . ?
C9 N3 C11 106.6(8) . . ?
C10 N3 C11 109.2(8) . . ?
C9 N3 Co1 109.2(6) . . ?
C10 N3 Co1 111.5(7) . . ?
C11 N3 Co1 112.9(6) . . ?
C10' N3' C11' 109.0(8) . . ?
C10' N3' C12' 108.4(10) . . ?
C11' N3' C12' 106.9(9) . . ?
C10' N3' Co1 112.5(7) . . ?
C11' N3' Co1 110.6(7) . . ?
C12' N3' Co1 109.3(7) . . ?
C14 N4 C13 118.7(4) . . ?
C14 N4 Co1 116.5(3) . . ?
C13 N4 Co1 116.7(3) . . ?
N1 C1 C2 119.4(4) . . ?
N1 C1 C14 110.9(4) . . ?
C2 C1 C14 129.4(5) . . ?
C3 C2 C1 118.9(5) . . ?
C3 C2 H2A 120.6 . . ?
C1 C2 H2A 120.6 . . ?
C2 C3 C4 120.1(4) . . ?
C2 C3 H3A 119.9 . . ?
C4 C3 H3A 119.9 . . ?
C5 C4 C3 119.2(4) . . ?
C5 C4 H4A 120.4 . . ?
C3 C4 H4A 120.4 . . ?
N1 C5 C4 119.2(4) . . ?
N1 C5 C6 111.7(4) . . ?
C4 C5 C6 128.7(4) . . ?
O1 C6 N2 128.2(5) . . ?
O1 C6 C5 121.3(4) . . ?
N2 C6 C5 110.4(4) . . ?
N2 C8 C9' 112.3(6) . . ?
N2 C8 C9 104.7(5) . . ?
N2 C8 H8A 110.5 . . ?
C9 C8 H8A 110.6 . . ?
N2 C8 H8B 110.8 . . ?
C9 C8 H8B 111.5 . . ?
H8A C8 H8B 108.8 . . ?
N2 C8 H8C 109.0 . . ?
C9' C8 H8C 109.2 . . ?
N2 C8 H8D 108.7 . . ?
C9' C8 H8D 109.7 . . ?
H8C C8 H8D 107.9 . . ?
N3 C9 C8 111.8(7) . . ?
N3 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
N3 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C11 C12 115.0(8) . . ?
N3 C11 H11A 108.5 . . ?
C12 C11 H11A 108.5 . . ?
N3 C11 H11B 108.5 . . ?
C12 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
C13 C12 C11 114.7(8) . . ?
C13 C12 H12A 108.6 . . ?
C11 C12 H12A 108.6 . . ?
C13 C12 H12B 108.6 . . ?
C11 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
C8 C9' C11' 118.3(10) . . ?
C8 C9' H9'A 107.7 . . ?
C11' C9' H9'A 107.7 . . ?
C8 C9' H9'B 107.7 . . ?
C11' C9' H9'B 107.7 . . ?
H9'A C9' H9'B 107.1 . . ?
N3' C10' H10D 109.5 . . ?
N3' C10' H10E 109.5 . . ?
H10D C10' H10E 109.5 . . ?
N3' C10' H10F 109.5 . . ?
H10D C10' H10F 109.5 . . ?
H10E C10' H10F 109.5 . . ?
N3' C11' C9' 115.8(9) . . ?
N3' C11' H11C 108.3 . . ?
C9' C11' H11C 108.3 . . ?
N3' C11' H11D 108.3 . . ?
C9' C11' H11D 108.3 . . ?
H11C C11' H11D 107.4 . . ?
N3' C12' C13 112.9(10) . . ?
N3' C12' H12C 109.0 . . ?
C13 C12' H12C 109.0 . . ?
N3' C12' H12D 109.0 . . ?
C13 C12' H12D 109.0 . . ?
H12C C12' H12D 107.8 . . ?
N4 C13 C12 114.6(6) . . ?
N4 C13 C12' 100.5(6) . . ?
N4 C13 H13A 108.6 . . ?
C12 C13 H13A 109.2 . . ?
N4 C13 H13B 108.6 . . ?
C12 C13 H13B 108.1 . . ?
H13A C13 H13B 107.6 . . ?
N4 C13 H13C 111.7 . . ?
C12' C13 H13C 111.9 . . ?
N4 C13 H13D 111.5 . . ?
C12' C13 H13D 111.5 . . ?
H13C C13 H13D 109.5 . . ?
O2 C14 N4 128.8(5) . . ?
O2 C14 C1 120.3(5) . . ?
N4 C14 C1 110.8(4) . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C17 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 C18 125.0(4) . . ?
O3 C17 C16 115.0(4) . . ?
C18 C17 C16 120.0(5) . . ?
C17 C18 C19 124.1(5) . . ?
C17 C18 H18A 118.0 . . ?
C19 C18 H18A 118.0 . . ?
O4 C19 C18 125.8(5) . . ?
O4 C19 C20 114.8(4) . . ?
C18 C19 C20 119.4(4) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
H1W O1W H2W 109(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 Co1 N1 C5 84.3(4) . . . . ?
N2 Co1 N1 C5 -10.9(3) . . . . ?
N4 Co1 N1 C5 178.9(4) . . . . ?
N3 Co1 N1 C5 -85.8(4) . . . . ?
N3' Co1 N1 C5 -106.1(4) . . . . ?
O4 Co1 N1 C1 -86.1(4) . . . . ?
N2 Co1 N1 C1 178.7(4) . . . . ?
N4 Co1 N1 C1 8.5(4) . . . . ?
N3 Co1 N1 C1 103.8(4) . . . . ?
N3' Co1 N1 C1 83.5(5) . . . . ?
C5 N1 C1 C2 2.0(7) . . . . ?
Co1 N1 C1 C2 171.9(4) . . . . ?
C5 N1 C1 C14 176.5(4) . . . . ?
Co1 N1 C1 C14 -13.7(5) . . . . ?
N1 C1 C2 C3 0.3(7) . . . . ?
C14 C1 C2 C3 -172.9(5) . . . . ?
C1 C2 C3 C4 -0.7(7) . . . . ?
C2 C3 C4 C5 -1.1(7) . . . . ?
C1 N1 C5 C4 -3.9(7) . . . . ?
Co1 N1 C5 C4 -173.8(3) . . . . ?
C1 N1 C5 C6 -177.1(4) . . . . ?
Co1 N1 C5 C6 13.0(5) . . . . ?
C3 C4 C5 N1 3.3(7) . . . . ?
C3 C4 C5 C6 175.2(5) . . . . ?
C8 N2 C6 O1 -28.1(8) . . . . ?
Co1 N2 C6 O1 -177.8(4) . . . . ?
C8 N2 C6 C5 149.1(4) . . . . ?
Co1 N2 C6 C5 -0.6(5) . . . . ?
N1 C5 C6 O1 169.8(4) . . . . ?
C4 C5 C6 O1 -2.6(8) . . . . ?
N1 C5 C6 N2 -7.6(6) . . . . ?
C4 C5 C6 N2 -180.0(5) . . . . ?
C6 N2 C8 C9' -93.6(8) . . . . ?
Co1 N2 C8 C9' 55.6(8) . . . . ?
C6 N2 C8 C9 -124.1(6) . . . . ?
Co1 N2 C8 C9 25.1(7) . . . . ?
C10 N3 C9 C8 86.2(9) . . . . ?
C11 N3 C9 C8 -157.0(8) . . . . ?
Co1 N3 C9 C8 -34.8(10) . . . . ?
N2 C8 C9 N3 7.8(10) . . . . ?
C9 N3 C11 C12 174.3(8) . . . . ?
C10 N3 C11 C12 -70.2(11) . . . . ?
Co1 N3 C11 C12 54.4(10) . . . . ?
N3 C11 C12 C13 -62.2(11) . . . . ?
N2 C8 C9' C11' -57.9(11) . . . . ?
C10' N3' C11' C9' 68.7(11) . . . . ?
C12' N3' C11' C9' -174.4(10) . . . . ?
Co1 N3' C11' C9' -55.5(10) . . . . ?
C8 C9' C11' N3' 61.9(12) . . . . ?
C10' N3' C12' C13 -101.7(11) . . . . ?
C11' N3' C12' C13 141.0(10) . . . . ?
Co1 N3' C12' C13 21.3(13) . . . . ?
C14 N4 C13 C12 90.6(7) . . . . ?
Co1 N4 C13 C12 -57.2(7) . . . . ?
C14 N4 C13 C12' 103.3(8) . . . . ?
Co1 N4 C13 C12' -44.5(7) . . . . ?
C11 C12 C13 N4 61.9(10) . . . . ?
N3' C12' C13 N4 11.3(12) . . . . ?
C13 N4 C14 O2 22.3(8) . . . . ?
Co1 N4 C14 O2 170.2(4) . . . . ?
C13 N4 C14 C1 -154.0(4) . . . . ?
Co1 N4 C14 C1 -6.2(5) . . . . ?
N1 C1 C14 O2 -164.5(4) . . . . ?
C2 C1 C14 O2 9.2(8) . . . . ?
N1 C1 C14 N4 12.3(6) . . . . ?
C2 C1 C14 N4 -174.0(5) . . . . ?
Co1 O3 C17 C18 -3.4(7) . . . . ?
Co1 O3 C17 C16 176.1(3) . . . . ?
O3 C17 C18 C19 -12.6(8) . . . . ?
C16 C17 C18 C19 167.9(5) . . . . ?
Co1 O4 C19 C18 8.0(7) . . . . ?
Co1 O4 C19 C20 -171.6(3) . . . . ?
C17 C18 C19 O4 10.0(9) . . . . ?
C17 C18 C19 C20 -170.3(5) . . . . ?

_refine_diff_density_max         1.339
_refine_diff_density_min         -0.811
_refine_diff_density_rms         0.124



