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

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

data_2
_database_code_depnum_ccdc_archive 'CCDC 1430329'
_audit_update_record             
;
2015-10-09 deposited with the CCDC.
2016-02-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(2,2'-bipyridine)-bis(7-fluoro-12-methyl-4-oxo-1-azatricyclo[7.3.1.05,13]trideca-2,5,7,9(13)-tetraene-3-carboxylato)-cobalt(II)-dihydrate 
;
_chemical_name_common            
;
(2,2'-bipyridine)-bis(flumequinato)-cobalt(II)-dihydrate
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H30 Co F2 N4 O6, 2(H2 O)'
_chemical_formula_sum            'C38 H34 Co F2 N4 O8'
_chemical_formula_weight         771.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2333(2)
_cell_length_b                   9.5588(3)
_cell_length_c                   20.9349(5)
_cell_angle_alpha                98.156(2)
_cell_angle_beta                 102.649(2)
_cell_angle_gamma                96.981(2)
_cell_volume                     1762.20(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7619
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             798
_exptl_absorpt_coefficient_mu    0.557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8733
_exptl_absorpt_correction_T_max  0.9361
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'

_exptl_special_details           
;
308 frames in 6 sets of φ scans + ω scans. Rotation/frame = 1.7 °.
Crystal-detector distance = 31.0 mm. Measuring time  = 60 s/°.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Nonius KappaCCD area-detector diffractometer
;
_diffrn_measurement_method       'φ scans + ω scans'
_diffrn_detector_area_resol_mean 0.055
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14676
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.67
_diffrn_reflns_theta_max         27.48
_reflns_number_total             7981
_reflns_number_gt                6268
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'KappaCCD Reference Manual (Nonius, 1998)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0625P)²+0.4746P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7981
_refine_ls_number_parameters     536
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1169
_refine_ls_wR_factor_gt          0.1064
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.50237(3) 0.48318(3) 0.731803(12) 0.04422(10) Uani 1 1 d . . .
F1 F 0.8082(2) 0.6252(3) 1.06938(8) 0.1229(8) Uani 1 1 d . . .
F2 F 0.0633(3) 0.1507(2) 0.43360(10) 0.1319(9) Uani 1 1 d . . .
N1 N 0.2776(2) 0.7641(2) 0.93853(9) 0.0611(5) Uani 1 1 d . A .
N2 N 0.3333(2) 0.7102(2) 0.50840(9) 0.0633(5) Uani 1 1 d . B .
N3 N 0.69075(17) 0.37764(17) 0.75863(7) 0.0419(3) Uani 1 1 d . . .
N4 N 0.40472(17) 0.2677(2) 0.72828(8) 0.0490(4) Uani 1 1 d . . .
O1 O 0.30213(17) 0.55568(19) 0.72083(7) 0.0624(4) Uani 1 1 d . . .
O2 O 0.12069(17) 0.66962(19) 0.74017(7) 0.0649(4) Uani 1 1 d . . .
O3 O 0.53804(16) 0.55841(18) 0.83336(7) 0.0576(4) Uani 1 1 d . . .
O4 O 0.62904(17) 0.66121(17) 0.71860(8) 0.0605(4) Uani 1 1 d . . .
O5 O 0.68990(19) 0.83884(17) 0.66738(9) 0.0684(4) Uani 1 1 d . . .
O6 O 0.45264(16) 0.42138(15) 0.62862(6) 0.0501(3) Uani 1 1 d . . .
C1 C 0.2406(2) 0.6267(2) 0.75928(9) 0.0420(4) Uani 1 1 d . . .
C2 C 0.3130(2) 0.6593(2) 0.83291(9) 0.0417(4) Uani 1 1 d . . .
C3 C 0.2333(2) 0.7269(2) 0.87275(10) 0.0525(5) Uani 1 1 d . . .
H3 H 0.1408 0.7484 0.8521 0.063 Uiso 1 1 calc R . .
C4 C 0.4537(2) 0.6219(2) 0.86321(9) 0.0432(4) Uani 1 1 d . . .
C5 C 0.5020(2) 0.6623(2) 0.93565(9) 0.0499(5) Uani 1 1 d . . .
C6 C 0.6375(3) 0.6270(3) 0.96881(11) 0.0651(6) Uani 1 1 d . . .
H6 H 0.6981 0.5805 0.9456 0.078 Uiso 1 1 calc R . .
C7 C 0.6781(3) 0.6631(4) 1.03659(12) 0.0845(9) Uani 1 1 d . . .
C8 C 0.5953(4) 0.7346(4) 1.07308(13) 0.0991(11) Uani 1 1 d . . .
H8 H 0.6283 0.7565 1.1191 0.119 Uiso 1 1 calc R . .
C9 C 0.4638(3) 0.7741(4) 1.04193(12) 0.0867(9) Uani 1 1 d . A .
C10 C 0.4142(3) 0.7336(3) 0.97222(10) 0.0592(6) Uani 1 1 d . . .
C11 C 0.3720(5) 0.8563(6) 1.08084(16) 0.1412(19) Uani 1 1 d . . .
H11A H 0.4381 0.9207 1.1188 0.169 Uiso 0.607(7) 1 calc PR A 1
H11B H 0.3060 0.7905 1.0971 0.169 Uiso 0.607(7) 1 calc PR A 1
H11C H 0.3917 0.9578 1.0795 0.169 Uiso 0.393(7) 1 calc PR A 2
H11D H 0.3949 0.8431 1.1269 0.169 Uiso 0.393(7) 1 calc PR A 2
C12A C 0.2760(7) 0.9446(8) 1.0344(3) 0.110(3) Uani 0.607(7) 1 d P A 1
H12A H 0.2146 0.9968 1.0582 0.132 Uiso 0.607(7) 1 calc PR A 1
H12B H 0.3409 1.0122 1.0186 0.132 Uiso 0.607(7) 1 calc PR A 1
C12B C 0.1874(12) 0.7857(16) 1.0419(4) 0.122(5) Uani 0.393(7) 1 d P A 2
H12C H 0.1697 0.6822 1.0374 0.147 Uiso 0.393(7) 1 calc PR A 2
H12D H 0.1181 0.8259 1.0653 0.147 Uiso 0.393(7) 1 calc PR A 2
C13 C 0.1754(3) 0.8324(4) 0.97538(13) 0.0819(9) Uani 1 1 d . . .
H13A H 0.1121 0.8830 0.9455 0.098 Uiso 0.607(7) 1 calc PR A 1
H13B H 0.0729 0.7941 0.9493 0.098 Uiso 0.393(7) 1 calc PR A 2
C14A C 0.0782(7) 0.7179(8) 0.9927(4) 0.117(3) Uani 0.607(7) 1 d P A 1
H14A H 0.0089 0.7589 1.0151 0.176 Uiso 0.607(7) 1 calc PR A 1
H14B H 0.1387 0.6662 1.0214 0.176 Uiso 0.607(7) 1 calc PR A 1
H14C H 0.0232 0.6538 0.9529 0.176 Uiso 0.607(7) 1 calc PR A 1
C14B C 0.1981(12) 0.9863(10) 0.9719(6) 0.110(4) Uani 0.393(7) 1 d P A 2
H14D H 0.3023 1.0256 0.9895 0.165 Uiso 0.393(7) 1 calc PR A 2
H14E H 0.1386 1.0346 0.9975 0.165 Uiso 0.393(7) 1 calc PR A 2
H14F H 0.1679 0.9987 0.9265 0.165 Uiso 0.393(7) 1 calc PR A 2
C15 C 0.6114(2) 0.7241(2) 0.66885(11) 0.0514(5) Uani 1 1 d . . .
C16 C 0.4888(2) 0.6598(2) 0.60821(9) 0.0470(4) Uani 1 1 d . . .
C17 C 0.4419(3) 0.7488(3) 0.56459(11) 0.0590(5) Uani 1 1 d . . .
H17 H 0.4892 0.8435 0.5748 0.071 Uiso 1 1 calc R . .
C18 C 0.4207(2) 0.5140(2) 0.59279(9) 0.0439(4) Uani 1 1 d . . .
C19 C 0.3074(2) 0.4707(2) 0.53000(9) 0.0511(5) Uani 1 1 d . . .
C20 C 0.2378(3) 0.3274(3) 0.51085(11) 0.0679(6) Uani 1 1 d . . .
H20 H 0.2641 0.2596 0.5372 0.081 Uiso 1 1 calc R . .
C21 C 0.1310(4) 0.2903(4) 0.45278(14) 0.0882(9) Uani 1 1 d . . .
C22 C 0.0829(4) 0.3870(4) 0.41315(13) 0.0913(9) Uani 1 1 d . . .
H22 H 0.0066 0.3567 0.3747 0.110 Uiso 1 1 calc R . .
C23 C 0.1473(3) 0.5270(4) 0.43046(11) 0.0739(7) Uani 1 1 d . B .
C24 C 0.2629(3) 0.5700(3) 0.48961(10) 0.0558(5) Uani 1 1 d . . .
C25 C 0.0986(4) 0.6355(4) 0.38862(15) 0.1019(11) Uani 1 1 d . . .
H25A H 0.1587 0.6408 0.3561 0.122 Uiso 0.552(5) 1 calc PR B 1
H25B H -0.0056 0.6048 0.3647 0.122 Uiso 0.552(5) 1 calc PR B 1
H25C H 0.0210 0.6807 0.4041 0.122 Uiso 0.448(5) 1 calc PR B 2
H25D H 0.0583 0.5897 0.3426 0.122 Uiso 0.448(5) 1 calc PR B 2
C26A C 0.1141(6) 0.7790(6) 0.4288(3) 0.0814(17) Uani 0.552(5) 1 d P B 1
H26A H 0.0518 0.7769 0.4605 0.098 Uiso 0.552(5) 1 calc PR B 1
H26B H 0.0841 0.8476 0.4004 0.098 Uiso 0.552(5) 1 calc PR B 1
C26B C 0.2453(12) 0.7542(11) 0.3950(3) 0.107(4) Uani 0.448(5) 1 d P B 2
H26C H 0.3255 0.7092 0.3819 0.128 Uiso 0.448(5) 1 calc PR B 2
H26D H 0.2203 0.8249 0.3671 0.128 Uiso 0.448(5) 1 calc PR B 2
C27 C 0.2914(4) 0.8225(3) 0.46731(13) 0.0833(8) Uani 1 1 d . . .
H27A H 0.3022 0.9127 0.4981 0.100 Uiso 0.607(7) 1 calc PR A 1
H27B H 0.3904 0.8766 0.4701 0.100 Uiso 0.393(7) 1 calc PR A 2
C28A C 0.3842(7) 0.8448(6) 0.4252(3) 0.0759(16) Uani 0.552(5) 1 d P B 1
H28A H 0.3500 0.9140 0.3987 0.114 Uiso 0.552(5) 1 calc PR B 1
H28B H 0.3821 0.7563 0.3966 0.114 Uiso 0.552(5) 1 calc PR B 1
H28C H 0.4851 0.8797 0.4508 0.114 Uiso 0.552(5) 1 calc PR B 1
C28B C 0.2284(12) 0.9202(10) 0.4976(4) 0.128(4) Uani 0.448(5) 1 d P B 2
H28D H 0.2932 0.9612 0.5403 0.191 Uiso 0.448(5) 1 calc PR B 2
H28E H 0.1337 0.8767 0.5032 0.191 Uiso 0.448(5) 1 calc PR B 2
H28F H 0.2124 0.9939 0.4713 0.191 Uiso 0.448(5) 1 calc PR B 2
C29 C 0.8336(2) 0.4430(2) 0.77799(10) 0.0519(5) Uani 1 1 d . . .
H29 H 0.8541 0.5410 0.7787 0.062 Uiso 1 1 calc R . .
C30 C 0.9518(2) 0.3698(3) 0.79701(11) 0.0580(5) Uani 1 1 d . . .
H30 H 1.0501 0.4180 0.8110 0.070 Uiso 1 1 calc R . .
C31 C 0.9216(2) 0.2248(3) 0.79490(12) 0.0603(6) Uani 1 1 d . . .
H31 H 0.9994 0.1733 0.8070 0.072 Uiso 1 1 calc R . .
C32 C 0.7755(2) 0.1567(2) 0.77476(11) 0.0548(5) Uani 1 1 d . . .
H32 H 0.7531 0.0585 0.7729 0.066 Uiso 1 1 calc R . .
C33 C 0.6616(2) 0.2365(2) 0.75719(9) 0.0423(4) Uani 1 1 d . . .
C34 C 0.4998(2) 0.1725(2) 0.73628(9) 0.0466(4) Uani 1 1 d . . .
C35 C 0.4482(3) 0.0271(3) 0.72486(14) 0.0689(6) Uani 1 1 d . . .
H35 H 0.5157 -0.0375 0.7307 0.083 Uiso 1 1 calc R . .
C36 C 0.2957(3) -0.0212(3) 0.70472(17) 0.0847(8) Uani 1 1 d . . .
H36 H 0.2592 -0.1186 0.6968 0.102 Uiso 1 1 calc R . .
C37 C 0.1986(3) 0.0758(3) 0.69646(16) 0.0816(8) Uani 1 1 d . . .
H37 H 0.0953 0.0453 0.6830 0.098 Uiso 1 1 calc R . .
C38 C 0.2560(2) 0.2177(3) 0.70838(13) 0.0660(6) Uani 1 1 d . . .
H38 H 0.1897 0.2833 0.7025 0.079 Uiso 1 1 calc R . .
O7 O -0.0407(2) 0.8874(2) 0.76208(11) 0.0738(5) Uani 1 1 d D . .
H1A H 0.010(2) 0.825(2) 0.7539(13) 0.067(8) Uiso 1 1 d D . .
H1B H -0.113(3) 0.882(5) 0.7300(14) 0.138(17) Uiso 1 1 d D . .
O8 O 0.8244(4) 0.8114(4) 0.86186(15) 0.1197(9) Uani 1 1 d D . .
H2A H 0.872(4) 0.837(4) 0.8352(17) 0.122(15) Uiso 1 1 d D . .
H2B H 0.7321(16) 0.794(7) 0.846(3) 0.20(3) Uiso 1 1 d D . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 2.0302(14) . ?
Co1 O4 2.0326(16) . ?
Co1 O3 2.0852(14) . ?
Co1 O6 2.0890(13) . ?
Co1 N3 2.1256(15) . ?
Co1 N4 2.1300(18) . ?
F1 C7 1.364(3) . ?
F2 C21 1.367(3) . ?
N1 C3 1.330(3) . ?
N1 C10 1.390(3) . ?
N1 C13 1.495(3) . ?
N2 C17 1.340(3) . ?
N2 C24 1.378(3) . ?
N2 C27 1.503(3) . ?
N3 C29 1.337(3) . ?
N3 C33 1.338(3) . ?
N4 C34 1.342(3) . ?
N4 C38 1.349(3) . ?
O1 C1 1.253(2) . ?
O2 C1 1.232(2) . ?
O3 C4 1.259(2) . ?
O4 C15 1.265(3) . ?
O5 C15 1.247(3) . ?
O6 C18 1.260(2) . ?
C1 C2 1.510(3) . ?
C2 C3 1.373(3) . ?
C2 C4 1.426(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.464(3) . ?
C5 C6 1.397(3) . ?
C5 C10 1.402(3) . ?
C6 C7 1.368(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.367(4) . ?
C8 C9 1.369(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.412(3) . ?
C9 C11 1.511(4) . ?
C11 C12A 1.574(8) . ?
C11 C12B 1.727(13) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C11 H11D 0.9700 . ?
C12A C13 1.555(7) . ?
C12A H12A 0.9700 . ?
C12A H12B 0.9700 . ?
C12B C13 1.507(10) . ?
C12B H12C 0.9700 . ?
C12B H12D 0.9700 . ?
C13 C14A 1.466(7) . ?
C13 C14B 1.474(10) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C14A H14A 0.9600 . ?
C14A H14B 0.9600 . ?
C14A H14C 0.9600 . ?
C14B H14D 0.9600 . ?
C14B H14E 0.9600 . ?
C14B H14F 0.9600 . ?
C15 C16 1.500(3) . ?
C16 C17 1.372(3) . ?
C16 C18 1.419(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.460(3) . ?
C19 C24 1.398(3) . ?
C19 C20 1.403(3) . ?
C20 C21 1.358(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.377(5) . ?
C22 C23 1.361(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.418(3) . ?
C23 C25 1.498(4) . ?
C25 C26A 1.477(7) . ?
C25 C26B 1.626(12) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 H25C 0.9700 . ?
C25 H25D 0.9700 . ?
C26A C27 1.633(6) . ?
C26A H26A 0.9700 . ?
C26A H26B 0.9700 . ?
C26B C27 1.507(8) . ?
C26B H26C 0.9700 . ?
C26B H26D 0.9700 . ?
C27 C28B 1.318(8) . ?
C27 C28A 1.377(6) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C28A H28A 0.9600 . ?
C28A H28B 0.9600 . ?
C28A H28C 0.9600 . ?
C28B H28D 0.9600 . ?
C28B H28E 0.9600 . ?
C28B H28F 0.9600 . ?
C29 C30 1.384(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.372(3) . ?
C30 H30 0.9300 . ?
C31 C32 1.371(3) . ?
C31 H31 0.9300 . ?
C32 C33 1.388(3) . ?
C32 H32 0.9300 . ?
C33 C34 1.488(3) . ?
C34 C35 1.382(3) . ?
C35 C36 1.379(4) . ?
C35 H35 0.9300 . ?
C36 C37 1.368(4) . ?
C36 H36 0.9300 . ?
C37 C38 1.363(4) . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?
O7 H1A 0.822(10) . ?
O7 H1B 0.826(10) . ?
O8 H2A 0.830(10) . ?
O8 H2B 0.832(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
O1 Co1 O4 98.45(7) . . ?
O1 Co1 O3 86.93(5) . . ?
O4 Co1 O3 92.15(7) . . ?
O1 Co1 O6 88.15(6) . . ?
O4 Co1 O6 86.52(6) . . ?
O3 Co1 O6 174.66(5) . . ?
O1 Co1 N3 166.17(7) . . ?
O4 Co1 N3 93.55(6) . . ?
O3 Co1 N3 85.78(6) . . ?
O6 Co1 N3 99.46(6) . . ?
O1 Co1 N4 93.52(7) . . ?
O4 Co1 N4 163.85(7) . . ?
O3 Co1 N4 99.33(7) . . ?
O6 Co1 N4 83.04(6) . . ?
N3 Co1 N4 76.13(6) . . ?
C3 N1 C10 119.90(18) . . ?
C3 N1 C13 119.1(2) . . ?
C10 N1 C13 120.99(19) . . ?
C17 N2 C24 119.83(19) . . ?
C17 N2 C27 118.5(2) . . ?
C24 N2 C27 121.6(2) . . ?
C29 N3 C33 118.75(16) . . ?
C29 N3 Co1 124.56(14) . . ?
C33 N3 Co1 116.68(12) . . ?
C34 N4 C38 118.1(2) . . ?
C34 N4 Co1 116.56(13) . . ?
C38 N4 Co1 124.43(16) . . ?
C1 O1 Co1 134.28(12) . . ?
C4 O3 Co1 128.18(12) . . ?
C15 O4 Co1 128.49(14) . . ?
C18 O6 Co1 118.45(12) . . ?
O2 C1 O1 123.06(17) . . ?
O2 C1 C2 117.53(16) . . ?
O1 C1 C2 119.39(16) . . ?
C3 C2 C4 118.78(17) . . ?
C3 C2 C1 116.29(16) . . ?
C4 C2 C1 124.91(16) . . ?
N1 C3 C2 125.32(19) . . ?
N1 C3 H3 117.3 . . ?
C2 C3 H3 117.3 . . ?
O3 C4 C2 125.95(17) . . ?
O3 C4 C5 118.21(17) . . ?
C2 C4 C5 115.83(17) . . ?
C6 C5 C10 119.61(19) . . ?
C6 C5 C4 118.98(19) . . ?
C10 C5 C4 121.41(18) . . ?
C7 C6 C5 117.7(2) . . ?
C7 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?
F1 C7 C8 118.5(2) . . ?
F1 C7 C6 118.0(3) . . ?
C8 C7 C6 123.6(3) . . ?
C7 C8 C9 120.1(2) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C8 C9 C10 118.3(3) . . ?
C8 C9 C11 121.3(3) . . ?
C10 C9 C11 120.5(3) . . ?
N1 C10 C5 118.75(18) . . ?
N1 C10 C9 120.6(2) . . ?
C5 C10 C9 120.6(2) . . ?
C9 C11 C12A 109.2(3) . . ?
C9 C11 C12B 104.7(4) . . ?
C12A C11 C12B 61.0(5) . . ?
C9 C11 H11A 109.8 . . ?
C12A C11 H11A 109.8 . . ?
C12B C11 H11A 145.1 . . ?
C9 C11 H11B 109.8 . . ?
C12A C11 H11B 109.8 . . ?
C12B C11 H11B 54.0 . . ?
H11A C11 H11B 108.3 . . ?
C9 C11 H11C 110.8 . . ?
C12A C11 H11C 52.0 . . ?
C12B C11 H11C 110.8 . . ?
H11A C11 H11C 60.5 . . ?
H11B C11 H11C 139.2 . . ?
C9 C11 H11D 110.8 . . ?
C12A C11 H11D 139.8 . . ?
C12B C11 H11D 110.8 . . ?
H11A C11 H11D 52.3 . . ?
H11B C11 H11D 58.6 . . ?
H11C C11 H11D 108.9 . . ?
C13 C12A C11 105.7(5) . . ?
C13 C12A H12A 110.6 . . ?
C11 C12A H12A 110.6 . . ?
C13 C12A H12B 110.6 . . ?
C11 C12A H12B 110.6 . . ?
H12A C12A H12B 108.7 . . ?
C13 C12B C11 100.7(7) . . ?
C13 C12B H12C 111.6 . . ?
C11 C12B H12C 111.6 . . ?
C13 C12B H12D 111.6 . . ?
C11 C12B H12D 111.6 . . ?
H12C C12B H12D 109.4 . . ?
C14A C13 C14B 144.1(5) . . ?
C14A C13 N1 107.8(3) . . ?
C14B C13 N1 107.3(4) . . ?
C14A C13 C12B 51.9(6) . . ?
C14B C13 C12B 119.7(7) . . ?
N1 C13 C12B 111.0(4) . . ?
C14A C13 C12A 116.4(4) . . ?
C14B C13 C12A 58.5(5) . . ?
N1 C13 C12A 107.4(3) . . ?
C12B C13 C12A 66.5(6) . . ?
C14A C13 H13A 108.4 . . ?
C14B C13 H13A 52.5 . . ?
N1 C13 H13A 108.4 . . ?
C12B C13 H13A 139.9 . . ?
C12A C13 H13A 108.4 . . ?
C14A C13 H13B 56.7 . . ?
C14B C13 H13B 106.0 . . ?
N1 C13 H13B 106.0 . . ?
C12B C13 H13B 106.0 . . ?
C12A C13 H13B 146.2 . . ?
H13A C13 H13B 54.9 . . ?
C13 C14A H14A 109.5 . . ?
C13 C14A H14B 109.5 . . ?
C13 C14A H14C 109.5 . . ?
C13 C14B H14D 109.5 . . ?
C13 C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
C13 C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
O5 C15 O4 123.5(2) . . ?
O5 C15 C16 117.4(2) . . ?
O4 C15 C16 119.07(19) . . ?
C17 C16 C18 118.36(19) . . ?
C17 C16 C15 117.12(19) . . ?
C18 C16 C15 124.51(18) . . ?
N2 C17 C16 125.2(2) . . ?
N2 C17 H17 117.4 . . ?
C16 C17 H17 117.4 . . ?
O6 C18 C16 124.79(18) . . ?
O6 C18 C19 118.96(19) . . ?
C16 C18 C19 116.24(18) . . ?
C24 C19 C20 119.2(2) . . ?
C24 C19 C18 121.4(2) . . ?
C20 C19 C18 119.3(2) . . ?
C21 C20 C19 118.2(3) . . ?
C21 C20 H20 120.9 . . ?
C19 C20 H20 120.9 . . ?
C20 C21 F2 118.6(3) . . ?
C20 C21 C22 123.5(3) . . ?
F2 C21 C22 117.9(3) . . ?
C23 C22 C21 119.8(2) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C24 118.7(3) . . ?
C22 C23 C25 121.5(3) . . ?
C24 C23 C25 119.8(3) . . ?
N2 C24 C19 118.76(19) . . ?
N2 C24 C23 120.7(2) . . ?
C19 C24 C23 120.5(2) . . ?
C26A C25 C23 112.2(3) . . ?
C26A C25 C26B 60.0(4) . . ?
C23 C25 C26B 107.6(3) . . ?
C26A C25 H25A 109.2 . . ?
C23 C25 H25A 109.2 . . ?
C26B C25 H25A 54.0 . . ?
C26A C25 H25B 109.2 . . ?
C23 C25 H25B 109.2 . . ?
C26B C25 H25B 142.9 . . ?
H25A C25 H25B 107.9 . . ?
C26A C25 H25C 52.1 . . ?
C23 C25 H25C 110.2 . . ?
C26B C25 H25C 110.2 . . ?
H25A C25 H25C 140.5 . . ?
H25B C25 H25C 60.8 . . ?
C26A C25 H25D 137.4 . . ?
C23 C25 H25D 110.2 . . ?
C26B C25 H25D 110.2 . . ?
H25A C25 H25D 59.0 . . ?
H25B C25 H25D 51.2 . . ?
H25C C25 H25D 108.5 . . ?
C25 C26A C27 106.1(4) . . ?
C25 C26A H26A 110.5 . . ?
C27 C26A H26A 110.5 . . ?
C25 C26A H26B 110.5 . . ?
C27 C26A H26B 110.5 . . ?
H26A C26A H26B 108.7 . . ?
C27 C26B C25 105.0(5) . . ?
C27 C26B H26C 110.7 . . ?
C25 C26B H26C 110.7 . . ?
C27 C26B H26D 110.7 . . ?
C25 C26B H26D 110.7 . . ?
H26C C26B H26D 108.8 . . ?
C28B C27 C28A 126.2(6) . . ?
C28B C27 C26B 126.9(5) . . ?
C28A C27 C26B 58.8(4) . . ?
C28B C27 N2 112.7(4) . . ?
C28A C27 N2 112.8(3) . . ?
C26B C27 N2 108.9(4) . . ?
C28B C27 C26A 77.2(6) . . ?
C28A C27 C26A 113.2(4) . . ?
C26B C27 C26A 59.3(4) . . ?
N2 C27 C26A 108.3(3) . . ?
C28A C27 H27A 107.4 . . ?
C26B C27 H27A 143.6 . . ?
N2 C27 H27A 107.4 . . ?
C26A C27 H27A 107.4 . . ?
C26B C27 H27B 101.3 . . ?
N2 C27 H27B 101.3 . . ?
C26A C27 H27B 148.5 . . ?
H27A C27 H27B 72.6 . . ?
C27 C28A H28A 109.5 . . ?
C27 C28A H28B 109.5 . . ?
C27 C28A H28C 109.5 . . ?
C27 C28B H28D 109.5 . . ?
C27 C28B H28E 109.5 . . ?
H28D C28B H28E 109.5 . . ?
C27 C28B H28F 109.5 . . ?
H28D C28B H28F 109.5 . . ?
H28E C28B H28F 109.5 . . ?
N3 C29 C30 122.2(2) . . ?
N3 C29 H29 118.9 . . ?
C30 C29 H29 118.9 . . ?
C31 C30 C29 118.9(2) . . ?
C31 C30 H30 120.6 . . ?
C29 C30 H30 120.6 . . ?
C32 C31 C30 119.33(19) . . ?
C32 C31 H31 120.3 . . ?
C30 C31 H31 120.3 . . ?
C31 C32 C33 119.1(2) . . ?
C31 C32 H32 120.5 . . ?
C33 C32 H32 120.5 . . ?
N3 C33 C32 121.77(18) . . ?
N3 C33 C34 115.36(16) . . ?
C32 C33 C34 122.86(19) . . ?
N4 C34 C35 121.5(2) . . ?
N4 C34 C33 114.60(18) . . ?
C35 C34 C33 123.90(19) . . ?
C36 C35 C34 119.2(2) . . ?
C36 C35 H35 120.4 . . ?
C34 C35 H35 120.4 . . ?
C37 C36 C35 119.4(3) . . ?
C37 C36 H36 120.3 . . ?
C35 C36 H36 120.3 . . ?
C38 C37 C36 118.7(2) . . ?
C38 C37 H37 120.6 . . ?
C36 C37 H37 120.6 . . ?
N4 C38 C37 123.1(2) . . ?
N4 C38 H38 118.5 . . ?
C37 C38 H38 118.5 . . ?
H1A O7 H1B 109(4) . . ?
H2A O8 H2B 113(5) . . ?

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
O1 Co1 N3 C29 -132.7(2) . . . . ?
O4 Co1 N3 C29 17.50(16) . . . . ?
O3 Co1 N3 C29 -74.40(16) . . . . ?
O6 Co1 N3 C29 104.56(16) . . . . ?
N4 Co1 N3 C29 -175.09(17) . . . . ?
O1 Co1 N3 C33 45.6(3) . . . . ?
O4 Co1 N3 C33 -164.14(13) . . . . ?
O3 Co1 N3 C33 103.97(13) . . . . ?
O6 Co1 N3 C33 -77.08(13) . . . . ?
N4 Co1 N3 C33 3.27(12) . . . . ?
O1 Co1 N4 C34 -177.70(14) . . . . ?
O4 Co1 N4 C34 44.5(3) . . . . ?
O3 Co1 N4 C34 -90.24(14) . . . . ?
O6 Co1 N4 C34 94.60(14) . . . . ?
N3 Co1 N4 C34 -6.98(13) . . . . ?
O1 Co1 N4 C38 13.33(18) . . . . ?
O4 Co1 N4 C38 -124.5(2) . . . . ?
O3 Co1 N4 C38 100.80(18) . . . . ?
O6 Co1 N4 C38 -74.37(18) . . . . ?
N3 Co1 N4 C38 -175.95(19) . . . . ?
O4 Co1 O1 C1 -85.4(2) . . . . ?
O3 Co1 O1 C1 6.3(2) . . . . ?
O6 Co1 O1 C1 -171.6(2) . . . . ?
N3 Co1 O1 C1 64.5(4) . . . . ?
N4 Co1 O1 C1 105.4(2) . . . . ?
O1 Co1 O3 C4 -1.21(19) . . . . ?
O4 Co1 O3 C4 97.15(19) . . . . ?
N3 Co1 O3 C4 -169.45(19) . . . . ?
N4 Co1 O3 C4 -94.27(19) . . . . ?
O1 Co1 O4 C15 -58.69(19) . . . . ?
O3 Co1 O4 C15 -145.91(18) . . . . ?
O6 Co1 O4 C15 28.92(18) . . . . ?
N3 Co1 O4 C15 128.19(18) . . . . ?
N4 Co1 O4 C15 78.7(3) . . . . ?
O1 Co1 O6 C18 54.68(15) . . . . ?
O4 Co1 O6 C18 -43.90(15) . . . . ?
N3 Co1 O6 C18 -136.93(14) . . . . ?
N4 Co1 O6 C18 148.45(15) . . . . ?
Co1 O1 C1 O2 173.65(17) . . . . ?
Co1 O1 C1 C2 -8.0(3) . . . . ?
O2 C1 C2 C3 3.9(3) . . . . ?
O1 C1 C2 C3 -174.6(2) . . . . ?
O2 C1 C2 C4 -177.9(2) . . . . ?
O1 C1 C2 C4 3.7(3) . . . . ?
C10 N1 C3 C2 -0.5(4) . . . . ?
C13 N1 C3 C2 -177.8(2) . . . . ?
C4 C2 C3 N1 1.4(3) . . . . ?
C1 C2 C3 N1 179.8(2) . . . . ?
Co1 O3 C4 C2 -1.2(3) . . . . ?
Co1 O3 C4 C5 178.80(14) . . . . ?
C3 C2 C4 O3 179.0(2) . . . . ?
C1 C2 C4 O3 0.8(3) . . . . ?
C3 C2 C4 C5 -1.0(3) . . . . ?
C1 C2 C4 C5 -179.23(18) . . . . ?
O3 C4 C5 C6 -1.1(3) . . . . ?
C2 C4 C5 C6 178.9(2) . . . . ?
O3 C4 C5 C10 179.8(2) . . . . ?
C2 C4 C5 C10 -0.2(3) . . . . ?
C10 C5 C6 C7 0.6(4) . . . . ?
C4 C5 C6 C7 -178.5(3) . . . . ?
C5 C6 C7 F1 178.2(3) . . . . ?
C5 C6 C7 C8 -1.7(5) . . . . ?
F1 C7 C8 C9 -179.8(3) . . . . ?
C6 C7 C8 C9 0.1(6) . . . . ?
C7 C8 C9 C10 2.6(6) . . . . ?
C7 C8 C9 C11 -178.5(4) . . . . ?
C3 N1 C10 C5 -0.7(4) . . . . ?
C13 N1 C10 C5 176.5(2) . . . . ?
C3 N1 C10 C9 179.2(3) . . . . ?
C13 N1 C10 C9 -3.7(4) . . . . ?
C6 C5 C10 N1 -178.1(2) . . . . ?
C4 C5 C10 N1 1.0(4) . . . . ?
C6 C5 C10 C9 2.1(4) . . . . ?
C4 C5 C10 C9 -178.8(3) . . . . ?
C8 C9 C10 N1 176.5(3) . . . . ?
C11 C9 C10 N1 -2.4(5) . . . . ?
C8 C9 C10 C5 -3.7(5) . . . . ?
C11 C9 C10 C5 177.4(3) . . . . ?
C8 C9 C11 C12A 154.4(4) . . . . ?
C10 C9 C11 C12A -26.7(6) . . . . ?
C8 C9 C11 C12B -141.6(5) . . . . ?
C10 C9 C11 C12B 37.2(7) . . . . ?
C9 C11 C12A C13 59.1(5) . . . . ?
C12B C11 C12A C13 -37.5(4) . . . . ?
C9 C11 C12B C13 -66.1(7) . . . . ?
C12A C11 C12B C13 37.9(5) . . . . ?
C3 N1 C13 C14A 89.3(4) . . . . ?
C10 N1 C13 C14A -87.9(4) . . . . ?
C3 N1 C13 C14B -83.1(6) . . . . ?
C10 N1 C13 C14B 99.7(6) . . . . ?
C3 N1 C13 C12B 144.5(7) . . . . ?
C10 N1 C13 C12B -32.7(7) . . . . ?
C3 N1 C13 C12A -144.7(4) . . . . ?
C10 N1 C13 C12A 38.2(5) . . . . ?
C11 C12B C13 C14A 160.7(9) . . . . ?
C11 C12B C13 C14B -61.7(8) . . . . ?
C11 C12B C13 N1 64.1(7) . . . . ?
C11 C12B C13 C12A -36.4(5) . . . . ?
C11 C12A C13 C14A 56.6(5) . . . . ?
C11 C12A C13 C14B -164.2(6) . . . . ?
C11 C12A C13 N1 -64.2(5) . . . . ?
C11 C12A C13 C12B 41.6(5) . . . . ?
Co1 O4 C15 O5 175.02(15) . . . . ?
Co1 O4 C15 C16 -4.2(3) . . . . ?
O5 C15 C16 C17 -19.2(3) . . . . ?
O4 C15 C16 C17 160.1(2) . . . . ?
O5 C15 C16 C18 159.88(19) . . . . ?
O4 C15 C16 C18 -20.8(3) . . . . ?
C24 N2 C17 C16 -2.2(4) . . . . ?
C27 N2 C17 C16 177.8(2) . . . . ?
C18 C16 C17 N2 1.5(3) . . . . ?
C15 C16 C17 N2 -179.4(2) . . . . ?
Co1 O6 C18 C16 37.0(2) . . . . ?
Co1 O6 C18 C19 -144.01(14) . . . . ?
C17 C16 C18 O6 -179.59(19) . . . . ?
C15 C16 C18 O6 1.4(3) . . . . ?
C17 C16 C18 C19 1.4(3) . . . . ?
C15 C16 C18 C19 -177.61(18) . . . . ?
O6 C18 C19 C24 177.28(18) . . . . ?
C16 C18 C19 C24 -3.7(3) . . . . ?
O6 C18 C19 C20 -0.5(3) . . . . ?
C16 C18 C19 C20 178.6(2) . . . . ?
C24 C19 C20 C21 1.1(4) . . . . ?
C18 C19 C20 C21 178.9(2) . . . . ?
C19 C20 C21 F2 179.6(3) . . . . ?
C19 C20 C21 C22 -2.9(5) . . . . ?
C20 C21 C22 C23 2.5(5) . . . . ?
F2 C21 C22 C23 180.0(3) . . . . ?
C21 C22 C23 C24 -0.3(5) . . . . ?
C21 C22 C23 C25 179.8(3) . . . . ?
C17 N2 C24 C19 -0.2(3) . . . . ?
C27 N2 C24 C19 179.9(2) . . . . ?
C17 N2 C24 C23 179.8(2) . . . . ?
C27 N2 C24 C23 -0.2(4) . . . . ?
C20 C19 C24 N2 -179.2(2) . . . . ?
C18 C19 C24 N2 3.1(3) . . . . ?
C20 C19 C24 C23 0.9(3) . . . . ?
C18 C19 C24 C23 -176.9(2) . . . . ?
C22 C23 C24 N2 178.7(2) . . . . ?
C25 C23 C24 N2 -1.4(4) . . . . ?
C22 C23 C24 C19 -1.3(4) . . . . ?
C25 C23 C24 C19 178.6(3) . . . . ?
C22 C23 C25 C26A 148.7(4) . . . . ?
C24 C23 C25 C26A -31.1(5) . . . . ?
C22 C23 C25 C26B -147.3(4) . . . . ?
C24 C23 C25 C26B 32.9(4) . . . . ?
C23 C25 C26A C27 58.8(5) . . . . ?
C26B C25 C26A C27 -39.3(4) . . . . ?
C26A C25 C26B C27 43.1(4) . . . . ?
C23 C25 C26B C27 -62.9(5) . . . . ?
C25 C26B C27 C28B -78.1(9) . . . . ?
C25 C26B C27 C28A 167.8(6) . . . . ?
C25 C26B C27 N2 62.0(5) . . . . ?
C25 C26B C27 C26A -38.5(4) . . . . ?
C17 N2 C27 C28B -66.7(7) . . . . ?
C24 N2 C27 C28B 113.2(6) . . . . ?
C17 N2 C27 C28A 83.8(4) . . . . ?
C24 N2 C27 C28A -96.2(4) . . . . ?
C17 N2 C27 C26B 147.0(5) . . . . ?
C24 N2 C27 C26B -33.0(5) . . . . ?
C17 N2 C27 C26A -150.1(3) . . . . ?
C24 N2 C27 C26A 29.9(4) . . . . ?
C25 C26A C27 C28B -168.0(6) . . . . ?
C25 C26A C27 C28A 67.8(5) . . . . ?
C25 C26A C27 C26B 43.5(5) . . . . ?
C25 C26A C27 N2 -58.1(4) . . . . ?
C33 N3 C29 C30 -0.5(3) . . . . ?
Co1 N3 C29 C30 177.84(16) . . . . ?
N3 C29 C30 C31 1.1(3) . . . . ?
C29 C30 C31 C32 -0.7(3) . . . . ?
C30 C31 C32 C33 -0.2(3) . . . . ?
C29 N3 C33 C32 -0.5(3) . . . . ?
Co1 N3 C33 C32 -178.93(15) . . . . ?
C29 N3 C33 C34 178.92(16) . . . . ?
Co1 N3 C33 C34 0.5(2) . . . . ?
C31 C32 C33 N3 0.8(3) . . . . ?
C31 C32 C33 C34 -178.52(19) . . . . ?
C38 N4 C34 C35 -0.2(3) . . . . ?
Co1 N4 C34 C35 -169.93(17) . . . . ?
C38 N4 C34 C33 179.01(18) . . . . ?
Co1 N4 C34 C33 9.3(2) . . . . ?
N3 C33 C34 N4 -6.4(2) . . . . ?
C32 C33 C34 N4 172.94(18) . . . . ?
N3 C33 C34 C35 172.8(2) . . . . ?
C32 C33 C34 C35 -7.8(3) . . . . ?
N4 C34 C35 C36 0.1(4) . . . . ?
C33 C34 C35 C36 -179.1(2) . . . . ?
C34 C35 C36 C37 0.0(4) . . . . ?
C35 C36 C37 C38 0.1(5) . . . . ?
C34 N4 C38 C37 0.3(4) . . . . ?
Co1 N4 C38 C37 169.2(2) . . . . ?
C36 C37 C38 N4 -0.3(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H1A O2 0.822(10) 1.928(10) 2.747(2) 175(3) .
O7 H1B O5 0.826(10) 1.956(15) 2.763(3) 165(4) 1_455
O8 H2A O7 0.830(10) 1.968(13) 2.792(4) 172(4) 1_655

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.042
####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1430330'
_audit_update_record             
;
2015-10-09 deposited with the CCDC.
2016-02-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
(1,10-phenanthroline)-bis(7-fluoro-12-methyl-4-oxo-1-azatricyclo[7.3.1.05,13]trideca-2,5,7,9(13)-tetraene-3-carboxylato)-cobalt(II)--methanol--water(1/1.6/0.4)
_chemical_name_common            
;
(1,10-phenanthroline)-bis(flumequinato)-cobalt(II)--methanol--water(1/1.6/0.4)
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H30 Co F2 N4 O6, 1.6(C H4 O), 0.4(H2O)'
_chemical_formula_sum            'C41.60 H37.20 Co F2 N4 O8'
_chemical_formula_weight         818.08

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'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 2/c'
_symmetry_space_group_name_Hall  '-P 2yc '

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

_cell_length_a                   11.4479(4)
_cell_length_b                   10.0270(3)
_cell_length_c                   18.5359(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.920(3)
_cell_angle_gamma                90.00
_cell_volume                     1929.60(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6458
_cell_measurement_theta_min      2.8185
_cell_measurement_theta_max      30.3692

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    0.513
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9043
_exptl_absorpt_correction_T_max  0.9505
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2011)'

_exptl_special_details           
;
398 frames in 5 runs of ω scans. Crystal-detector distance = 55.0 mm. 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18417
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.82
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4412
_reflns_number_gt                3556
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1111P)²+0.9250P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4412
_refine_ls_number_parameters     291
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0612
_refine_ls_wR_factor_ref         0.1887
_refine_ls_wR_factor_gt          0.1766
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.0000 0.62852(5) 0.2500 0.0412(2) Uani 1 2 d S . .
F1 F 0.6480(3) 0.5134(4) 0.3763(3) 0.1624(17) Uani 1 1 d . . .
O1 O 0.0375(3) 0.8705(3) 0.44186(15) 0.0758(8) Uani 1 1 d . . .
O2 O -0.00945(19) 0.7589(2) 0.33102(13) 0.0551(5) Uani 1 1 d . . .
O3 O 0.1979(2) 0.6301(2) 0.31640(14) 0.0562(6) Uani 1 1 d . . .
N1 N 0.4165(3) 0.7950(4) 0.5342(2) 0.0811(10) Uani 1 1 d . A .
N2 N 0.0321(2) 0.4606(2) 0.18833(13) 0.0456(5) Uani 1 1 d . . .
C1 C 0.0692(3) 0.8002(3) 0.39772(16) 0.0482(6) Uani 1 1 d . . .
C2 C 0.2094(3) 0.7645(3) 0.42575(16) 0.0497(7) Uani 1 1 d . . .
C3 C 0.2902(4) 0.8152(4) 0.4995(2) 0.0672(9) Uani 1 1 d . . .
H3 H 0.2537 0.8666 0.5264 0.081 Uiso 1 1 calc R . .
C4 C 0.2606(3) 0.6864(3) 0.38232(18) 0.0500(7) Uani 1 1 d . . .
C5 C 0.4010(3) 0.6695(4) 0.4193(2) 0.0634(9) Uani 1 1 d . . .
C6 C 0.4752(3) 0.7240(4) 0.4964(3) 0.0778(12) Uani 1 1 d . . .
C7 C 0.4588(4) 0.6002(4) 0.3779(3) 0.0839(13) Uani 1 1 d . . .
H7 H 0.4113 0.5678 0.3268 0.101 Uiso 1 1 calc R . .
C8 C 0.5902(5) 0.5820(6) 0.4166(5) 0.113(2) Uani 1 1 d . . .
C9 C 0.6628(5) 0.6341(6) 0.4909(5) 0.125(3) Uani 1 1 d . . .
H9 H 0.7517 0.6227 0.5134 0.150 Uiso 1 1 calc R . .
C10 C 0.6086(5) 0.7009(7) 0.5315(4) 0.123(2) Uani 1 1 d U A .
C11 C 0.6897(6) 0.7553(10) 0.6138(5) 0.168(3) Uani 1 1 d U . .
H11A H 0.7198 0.8441 0.6097 0.202 Uiso 0.504(18) 1 calc PR A 1
H11B H 0.7641 0.6985 0.6407 0.202 Uiso 0.504(18) 1 calc PR A 1
H11C H 0.7803 0.7563 0.6247 0.202 Uiso 0.496(18) 1 d PR A 2
H11D H 0.6779 0.7034 0.6544 0.202 Uiso 0.496(18) 1 d PR A 2
C12A C 0.5992(12) 0.7607(15) 0.6667(6) 0.105(5) Uani 0.504(18) 1 d P A 1
H12A H 0.5637 0.6740 0.6696 0.126 Uiso 0.504(18) 1 calc PR A 1
H12B H 0.6475 0.7953 0.7200 0.126 Uiso 0.504(18) 1 calc PR A 1
C12B C 0.6338(18) 0.903(2) 0.6100(8) 0.179(15) Uani 0.496(18) 1 d P A 2
H12C H 0.6197 0.9485 0.5608 0.215 Uiso 0.496(18) 1 calc PR A 2
H12D H 0.6879 0.9571 0.6551 0.215 Uiso 0.496(18) 1 calc PR A 2
C13 C 0.4943(6) 0.8588(6) 0.6141(3) 0.1083(19) Uani 1 1 d . . .
H13A H 0.4349 0.8675 0.6395 0.130 Uiso 0.504(18) 1 calc PR A 1
H13B H 0.4534 0.9437 0.6161 0.130 Uiso 0.496(18) 1 d PR A 2
C14A C 0.5295(14) 0.9913(11) 0.6047(6) 0.095(4) Uani 0.504(18) 1 d P A 1
H14A H 0.5904 0.9894 0.5815 0.143 Uiso 0.504(18) 1 calc PR A 1
H14B H 0.5677 1.0342 0.6556 0.143 Uiso 0.504(18) 1 calc PR A 1
H14C H 0.4542 1.0398 0.5704 0.143 Uiso 0.504(18) 1 calc PR A 1
C14B C 0.502(3) 0.786(2) 0.6708(7) 0.196(13) Uani 0.496(18) 1 d P A 2
H14D H 0.5605 0.7142 0.6771 0.293 Uiso 0.496(18) 1 calc PR A 2
H14E H 0.4180 0.7505 0.6600 0.293 Uiso 0.496(18) 1 calc PR A 2
H14F H 0.5318 0.8380 0.7188 0.293 Uiso 0.496(18) 1 calc PR A 2
C15 C 0.0666(4) 0.4632(4) 0.1291(2) 0.0626(8) Uani 1 1 d . . .
H15 H 0.0786 0.5455 0.1100 0.075 Uiso 1 1 calc R . .
C16 C 0.0860(5) 0.3466(5) 0.0933(3) 0.0843(13) Uani 1 1 d . . .
H16 H 0.1102 0.3522 0.0513 0.101 Uiso 1 1 calc R . .
C17 C 0.0692(4) 0.2264(4) 0.1205(2) 0.0771(11) Uani 1 1 d . . .
H17 H 0.0792 0.1488 0.0962 0.093 Uiso 1 1 calc R . .
C18 C 0.0366(3) 0.2188(3) 0.1856(2) 0.0579(8) Uani 1 1 d . . .
C19 C 0.0176(3) 0.3398(3) 0.21721(17) 0.0446(6) Uani 1 1 d . . .
C20 C 0.0170(4) 0.0964(3) 0.2200(2) 0.0687(10) Uani 1 1 d . . .
H20 H 0.0287 0.0154 0.1996 0.082 Uiso 1 1 calc R . .
O4 O 0.2264(6) 1.0753(7) 0.6079(6) 0.155(3) Uani 0.800(9) 1 d P B 1
H4 H 0.1741 1.1275 0.5769 0.232 Uiso 0.800(9) 1 calc PR B 1
C21 C 0.2969(8) 1.1407(10) 0.6833(6) 0.131(3) Uani 0.800(9) 1 d P B 1
H21A H 0.3847 1.1109 0.7057 0.197 Uiso 0.800(9) 1 calc PR B 1
H21B H 0.2584 1.1193 0.7190 0.197 Uiso 0.800(9) 1 calc PR B 1
H21C H 0.2944 1.2355 0.6754 0.197 Uiso 0.800(9) 1 calc PR B 1
O5 O 0.1572(15) 1.0953(16) 0.5278(10) 0.090(6) Uani 0.200(9) 1 d P B 2


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 2.028(2) 2 ?
Co1 O2 2.028(2) . ?
Co1 O3 2.073(2) 2 ?
Co1 O3 2.073(2) . ?
Co1 N2 2.152(2) . ?
Co1 N2 2.152(2) 2 ?
F1 C8 1.372(7) . ?
O1 C1 1.244(4) . ?
O2 C1 1.254(3) . ?
O3 C4 1.260(4) . ?
N1 C3 1.327(5) . ?
N1 C6 1.360(6) . ?
N1 C13 1.512(5) . ?
N2 C15 1.314(4) . ?
N2 C19 1.362(4) . ?
C1 C2 1.507(4) . ?
C2 C3 1.385(4) . ?
C2 C4 1.415(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.467(4) . ?
C5 C7 1.392(7) . ?
C5 C6 1.428(6) . ?
C6 C10 1.404(6) . ?
C7 C8 1.379(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.377(10) . ?
C9 C10 1.339(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.514(9) . ?
C11 C12B 1.60(3) . ?
C11 C12A 1.702(17) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C11 H11D 0.9700 . ?
C12A C13 1.541(13) . ?
C12A H11D 1.1697 . ?
C12A H12A 0.9700 . ?
C12A H12B 0.9700 . ?
C12B C13 1.690(19) . ?
C12B H12C 0.9700 . ?
C12B H12D 0.9700 . ?
C13 C14B 1.253(17) . ?
C13 C14A 1.421(11) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C14A H13B 1.0902 . ?
C14A H14A 0.9600 . ?
C14A H14B 0.9600 . ?
C14A H14C 0.9600 . ?
C14B H14D 0.9600 . ?
C14B H14E 0.9600 . ?
C14B H14F 0.9600 . ?
C15 C16 1.408(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.351(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.409(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.403(4) . ?
C18 C20 1.443(5) . ?
C19 C19 1.433(6) 2 ?
C20 C20 1.323(8) 2 ?
C20 H20 0.9300 . ?
O4 C21 1.444(11) . ?
O4 H4 0.8200 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Co1 O2 99.71(14) 2 . ?
O2 Co1 O3 86.63(9) 2 2 ?
O2 Co1 O3 92.79(9) . 2 ?
O2 Co1 O3 92.79(9) 2 . ?
O2 Co1 O3 86.63(9) . . ?
O3 Co1 O3 179.11(13) 2 . ?
O2 Co1 N2 92.11(9) 2 . ?
O2 Co1 N2 166.43(9) . . ?
O3 Co1 N2 94.55(9) 2 . ?
O3 Co1 N2 86.15(9) . . ?
O2 Co1 N2 166.43(9) 2 2 ?
O2 Co1 N2 92.11(9) . 2 ?
O3 Co1 N2 86.15(9) 2 2 ?
O3 Co1 N2 94.55(9) . 2 ?
N2 Co1 N2 77.04(13) . 2 ?
C1 O2 Co1 134.6(2) . . ?
C4 O3 Co1 127.8(2) . . ?
C3 N1 C6 120.3(3) . . ?
C3 N1 C13 118.8(4) . . ?
C6 N1 C13 120.7(4) . . ?
C15 N2 C19 118.4(3) . . ?
C15 N2 Co1 127.3(2) . . ?
C19 N2 Co1 114.23(18) . . ?
O1 C1 O2 123.3(3) . . ?
O1 C1 C2 118.1(3) . . ?
O2 C1 C2 118.7(3) . . ?
C3 C2 C4 120.0(3) . . ?
C3 C2 C1 115.2(3) . . ?
C4 C2 C1 124.8(2) . . ?
N1 C3 C2 124.1(4) . . ?
N1 C3 H3 117.9 . . ?
C2 C3 H3 117.9 . . ?
O3 C4 C2 126.6(3) . . ?
O3 C4 C5 117.8(3) . . ?
C2 C4 C5 115.7(3) . . ?
C7 C5 C6 121.4(4) . . ?
C7 C5 C4 118.8(4) . . ?
C6 C5 C4 119.8(4) . . ?
N1 C6 C10 121.7(5) . . ?
N1 C6 C5 120.1(3) . . ?
C10 C6 C5 118.3(5) . . ?
C8 C7 C5 116.6(5) . . ?
C8 C7 H7 121.7 . . ?
C5 C7 H7 121.7 . . ?
F1 C8 C9 120.6(5) . . ?
F1 C8 C7 117.0(6) . . ?
C9 C8 C7 122.4(6) . . ?
C10 C9 C8 121.7(5) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C10 C6 119.5(6) . . ?
C9 C10 C11 120.9(5) . . ?
C6 C10 C11 119.5(7) . . ?
C10 C11 C12B 103.0(7) . . ?
C10 C11 C12A 109.2(6) . . ?
C12B C11 C12A 70.6(9) . . ?
C10 C11 H11A 109.8 . . ?
C12B C11 H11A 45.3 . . ?
C12A C11 H11A 109.8 . . ?
C10 C11 H11B 109.8 . . ?
C12B C11 H11B 144.3 . . ?
C12A C11 H11B 109.8 . . ?
H11A C11 H11B 108.3 . . ?
C10 C11 H11C 111.2 . . ?
C12B C11 H11C 111.8 . . ?
C12A C11 H11C 137.4 . . ?
H11A C11 H11C 67.8 . . ?
C10 C11 H11D 111.2 . . ?
C12B C11 H11D 110.3 . . ?
H11A C11 H11D 136.4 . . ?
H11B C11 H11D 70.5 . . ?
H11C C11 H11D 109.2 . . ?
C13 C12A C11 99.0(8) . . ?
C13 C12A H11D 130.4 . . ?
C13 C12A H12A 112.0 . . ?
C11 C12A H12A 112.0 . . ?
H11D C12A H12A 86.9 . . ?
C13 C12A H12B 112.0 . . ?
C11 C12A H12B 112.0 . . ?
H11D C12A H12B 102.6 . . ?
H12A C12A H12B 109.7 . . ?
C11 C12B C13 97.0(9) . . ?
C11 C12B H12C 112.4 . . ?
C13 C12B H12C 112.4 . . ?
C11 C12B H12D 112.4 . . ?
C13 C12B H12D 112.4 . . ?
H12C C12B H12D 109.9 . . ?
C14B C13 C14A 136.5(10) . . ?
C14B C13 N1 112.3(9) . . ?
C14A C13 N1 110.8(6) . . ?
C14B C13 C12A 48.6(14) . . ?
C14A C13 C12A 119.3(8) . . ?
N1 C13 C12A 109.3(6) . . ?
C14B C13 C12B 117.5(14) . . ?
C14A C13 C12B 55.0(8) . . ?
N1 C13 C12B 104.2(7) . . ?
C12A C13 C12B 72.4(9) . . ?
C14B C13 H13A 57.5 . . ?
C14A C13 H13A 105.4 . . ?
N1 C13 H13A 105.4 . . ?
C12A C13 H13A 105.4 . . ?
C12B C13 H13A 149.1 . . ?
C14B C13 H13B 109.7 . . ?
C14A C13 H13B 50.0 . . ?
N1 C13 H13B 108.1 . . ?
C12A C13 H13B 142.0 . . ?
C12B C13 H13B 104.5 . . ?
H13A C13 H13B 57.6 . . ?
C13 C14A H14A 109.5 . . ?
H13B C14A H14A 150.3 . . ?
C13 C14A H14B 109.5 . . ?
H13B C14A H14B 94.3 . . ?
C13 C14A H14C 109.5 . . ?
H13B C14A H14C 77.4 . . ?
C13 C14B H14D 109.5 . . ?
C13 C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
C13 C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
N2 C15 C16 122.7(3) . . ?
N2 C15 H15 118.7 . . ?
C16 C15 H15 118.7 . . ?
C17 C16 C15 119.3(4) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C16 C17 C18 120.0(3) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 117.0(3) . . ?
C19 C18 C20 118.1(3) . . ?
C17 C18 C20 124.8(3) . . ?
N2 C19 C18 122.6(3) . . ?
N2 C19 C19 117.25(15) . 2 ?
C18 C19 C19 120.1(2) . 2 ?
C20 C20 C18 121.8(2) 2 . ?
C20 C20 H20 119.1 2 . ?
C18 C20 H20 119.1 . . ?

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
O2 Co1 O2 C1 -103.1(3) 2 . . . ?
O3 Co1 O2 C1 169.9(3) 2 . . . ?
O3 Co1 O2 C1 -10.8(3) . . . . ?
N2 Co1 O2 C1 47.1(5) . . . . ?
N2 Co1 O2 C1 83.6(3) 2 . . . ?
O2 Co1 O3 C4 105.6(3) 2 . . . ?
O2 Co1 O3 C4 6.1(3) . . . . ?
N2 Co1 O3 C4 -162.4(3) . . . . ?
N2 Co1 O3 C4 -85.8(3) 2 . . . ?
O2 Co1 N2 C15 10.0(3) 2 . . . ?
O2 Co1 N2 C15 -140.7(4) . . . . ?
O3 Co1 N2 C15 96.7(3) 2 . . . ?
O3 Co1 N2 C15 -82.7(3) . . . . ?
N2 Co1 N2 C15 -178.3(3) 2 . . . ?
O2 Co1 N2 C19 -171.98(18) 2 . . . ?
O2 Co1 N2 C19 37.4(4) . . . . ?
O3 Co1 N2 C19 -85.20(19) 2 . . . ?
O3 Co1 N2 C19 95.36(19) . . . . ?
N2 Co1 N2 C19 -0.21(13) 2 . . . ?
Co1 O2 C1 O1 -171.3(2) . . . . ?
Co1 O2 C1 C2 9.4(4) . . . . ?
O1 C1 C2 C3 -0.1(4) . . . . ?
O2 C1 C2 C3 179.2(3) . . . . ?
O1 C1 C2 C4 -179.5(3) . . . . ?
O2 C1 C2 C4 -0.2(4) . . . . ?
C6 N1 C3 C2 2.0(6) . . . . ?
C13 N1 C3 C2 178.6(4) . . . . ?
C4 C2 C3 N1 -0.4(5) . . . . ?
C1 C2 C3 N1 -179.9(3) . . . . ?
Co1 O3 C4 C2 -1.3(4) . . . . ?
Co1 O3 C4 C5 178.0(2) . . . . ?
C3 C2 C4 O3 177.0(3) . . . . ?
C1 C2 C4 O3 -3.5(5) . . . . ?
C3 C2 C4 C5 -2.3(4) . . . . ?
C1 C2 C4 C5 177.2(3) . . . . ?
O3 C4 C5 C7 4.2(5) . . . . ?
C2 C4 C5 C7 -176.4(3) . . . . ?
O3 C4 C5 C6 -175.9(3) . . . . ?
C2 C4 C5 C6 3.5(5) . . . . ?
C3 N1 C6 C10 -179.9(5) . . . . ?
C13 N1 C6 C10 3.6(7) . . . . ?
C3 N1 C6 C5 -0.7(6) . . . . ?
C13 N1 C6 C5 -177.2(4) . . . . ?
C7 C5 C6 N1 177.8(4) . . . . ?
C4 C5 C6 N1 -2.1(6) . . . . ?
C7 C5 C6 C10 -2.9(7) . . . . ?
C4 C5 C6 C10 177.2(4) . . . . ?
C6 C5 C7 C8 2.8(6) . . . . ?
C4 C5 C7 C8 -177.3(4) . . . . ?
C5 C7 C8 F1 179.8(4) . . . . ?
C5 C7 C8 C9 -2.8(8) . . . . ?
F1 C8 C9 C10 -179.7(6) . . . . ?
C7 C8 C9 C10 3.0(11) . . . . ?
C8 C9 C10 C6 -3.0(11) . . . . ?
C8 C9 C10 C11 178.9(7) . . . . ?
N1 C6 C10 C9 -177.8(6) . . . . ?
C5 C6 C10 C9 2.9(9) . . . . ?
N1 C6 C10 C11 0.4(10) . . . . ?
C5 C6 C10 C11 -178.9(6) . . . . ?
C9 C10 C11 C12B 135.1(9) . . . . ?
C6 C10 C11 C12B -43.0(12) . . . . ?
C9 C10 C11 C12A -151.2(8) . . . . ?
C6 C10 C11 C12A 30.6(11) . . . . ?
C10 C11 C12A C13 -61.7(10) . . . . ?
C12B C11 C12A C13 35.8(7) . . . . ?
C10 C11 C12B C13 74.0(9) . . . . ?
C12A C11 C12B C13 -32.0(6) . . . . ?
C3 N1 C13 C14B 89.0(18) . . . . ?
C6 N1 C13 C14B -94.5(19) . . . . ?
C3 N1 C13 C14A -85.3(9) . . . . ?
C6 N1 C13 C14A 91.2(9) . . . . ?
C3 N1 C13 C12A 141.1(7) . . . . ?
C6 N1 C13 C12A -42.3(9) . . . . ?
C3 N1 C13 C12B -142.9(10) . . . . ?
C6 N1 C13 C12B 33.7(11) . . . . ?
C11 C12A C13 C14B 169.1(17) . . . . ?
C11 C12A C13 C14A -63.0(11) . . . . ?
C11 C12A C13 N1 66.0(8) . . . . ?
C11 C12A C13 C12B -33.3(9) . . . . ?
C11 C12B C13 C14B 54.2(15) . . . . ?
C11 C12B C13 C14A -176.4(11) . . . . ?
C11 C12B C13 N1 -70.7(8) . . . . ?
C11 C12B C13 C12A 35.4(7) . . . . ?
C19 N2 C15 C16 1.5(5) . . . . ?
Co1 N2 C15 C16 179.5(3) . . . . ?
N2 C15 C16 C17 -0.2(7) . . . . ?
C15 C16 C17 C18 -2.0(7) . . . . ?
C16 C17 C18 C19 2.7(6) . . . . ?
C16 C17 C18 C20 -179.6(4) . . . . ?
C15 N2 C19 C18 -0.7(4) . . . . ?
Co1 N2 C19 C18 -179.0(2) . . . . ?
C15 N2 C19 C19 178.8(3) . . . 2 ?
Co1 N2 C19 C19 0.6(4) . . . 2 ?
C17 C18 C19 N2 -1.3(5) . . . . ?
C20 C18 C19 N2 -179.2(3) . . . . ?
C17 C18 C19 C19 179.1(3) . . . 2 ?
C20 C18 C19 C19 1.2(5) . . . 2 ?
C19 C18 C20 C20 -0.4(6) . . . 2 ?
C17 C18 C20 C20 -178.1(5) . . . 2 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4 O1 0.82 2.30 2.815(6) 121.5 3_576

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.749
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.069
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1430331'
_audit_update_record             
;
2015-10-09 deposited with the CCDC.
2016-02-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
(di(2-pyridyl)amine-N,N')-bis(7-fluoro-12-methyl-4-oxo-1-azatricyclo[7.3.1.05,13]trideca-2,5,7,9(13)-tetraene-3-carboxylato-O,O')-cobalt(II)--hydrate
_chemical_name_common            
;
(di(2-pyridyl)amine-N,N')-bis(flumequinato-O,O')-cobalt(II)--hydrate
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H33 Co F2 N5 O6, H2O'
_chemical_formula_sum            'C38 H33 Co F2 N5 O7'
_chemical_formula_weight         768.62

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   11.5948(10)
_cell_length_b                   24.2372(15)
_cell_length_c                   12.5448(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.391(8)
_cell_angle_gamma                90.00
_cell_volume                     3456.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3853
_cell_measurement_theta_min      2.7932
_cell_measurement_theta_max      30.4686

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1588
_exptl_absorpt_coefficient_mu    0.567
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9455
_exptl_absorpt_correction_T_max  0.9722
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2011)'

_exptl_special_details           
;
220 frames in 3 runs of ω scans. Crystal-detector distance = 55.0 mm. 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  Mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18382
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_sigmaI/netI    0.0603
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.80
_diffrn_reflns_theta_max         27.48
_reflns_number_total             7890
_reflns_number_gt                5212
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0842P)²+2.6460P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7890
_refine_ls_number_parameters     491
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1013
_refine_ls_R_factor_gt           0.0655
_refine_ls_wR_factor_ref         0.1914
_refine_ls_wR_factor_gt          0.1676
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.67930(4) 0.051347(18) 0.81762(4) 0.04006(17) Uani 1 1 d . . .
F1 F 0.8817(3) 0.30888(11) 0.9568(2) 0.0836(9) Uani 1 1 d . . .
F2 F 0.8201(3) 0.19575(13) 0.4124(2) 0.0834(9) Uani 1 1 d . . .
N1 N 0.5488(3) -0.00976(13) 0.7743(3) 0.0482(8) Uani 1 1 d . . .
N2 N 0.7392(3) 0.00468(11) 0.9599(2) 0.0427(7) Uani 1 1 d . . .
N3 N 0.5665(3) -0.04752(12) 0.9500(3) 0.0473(8) Uani 1 1 d . . .
H3A H 0.5280 -0.0661 0.9899 0.057 Uiso 1 1 calc R . .
N4 N 1.0308(3) 0.16776(13) 0.6712(2) 0.0471(8) Uani 1 1 d . . .
N5 N 0.5833(3) 0.26972(12) 0.7222(3) 0.0501(8) Uani 1 1 d . . .
O1 O 0.7924(3) 0.01539(10) 0.7350(2) 0.0530(7) Uani 1 1 d . . .
O2 O 0.8848(4) 0.01932(15) 0.5980(3) 0.1011(15) Uani 1 1 d . . .
O3 O 0.8078(2) 0.11247(10) 0.8618(2) 0.0450(6) Uani 1 1 d . . .
O4 O 0.5646(2) 0.09535(10) 0.8901(2) 0.0478(6) Uani 1 1 d . . .
O5 O 0.4569(3) 0.16523(12) 0.9241(3) 0.0741(10) Uani 1 1 d . . .
O6 O 0.6223(2) 0.10383(10) 0.6806(2) 0.0446(6) Uani 1 1 d . . .
C1 C 0.8563(4) 0.03972(16) 0.6793(3) 0.0508(10) Uani 1 1 d . . .
C2 C 0.9039(3) 0.09618(14) 0.7137(3) 0.0399(8) Uani 1 1 d . . .
C3 C 0.9839(3) 0.11782(16) 0.6571(3) 0.0442(8) Uani 1 1 d . . .
H3 H 1.0069 0.0955 0.6047 0.053 Uiso 1 1 calc R . .
C4 C 0.8736(3) 0.12791(14) 0.7982(3) 0.0370(7) Uani 1 1 d . . .
C5 C 0.9195(3) 0.18434(14) 0.8094(3) 0.0402(8) Uani 1 1 d . . .
C6 C 0.8808(3) 0.22020(16) 0.8819(3) 0.0468(9) Uani 1 1 d . . .
H6 H 0.8300 0.2080 0.9258 0.056 Uiso 1 1 calc R . .
C7 C 0.9191(4) 0.27335(17) 0.8870(3) 0.0570(11) Uani 1 1 d . . .
C8 C 0.9919(4) 0.29338(19) 0.8226(4) 0.0644(12) Uani 1 1 d . . .
H8 H 1.0144 0.3303 0.8278 0.077 Uiso 1 1 calc R . .
C9 C 1.0318(4) 0.25940(18) 0.7507(3) 0.0577(11) Uani 1 1 d . . .
C10 C 0.9958(3) 0.20378(15) 0.7446(3) 0.0427(8) Uani 1 1 d . . .
C11 C 1.1128(6) 0.2799(2) 0.6785(5) 0.0914(19) Uani 1 1 d . . .
H11A H 1.1928 0.2807 0.7198 0.110 Uiso 1 1 calc R . .
H11B H 1.0908 0.3172 0.6552 0.110 Uiso 1 1 calc R . .
C12 C 1.1074(7) 0.2435(3) 0.5796(6) 0.115(2) Uani 1 1 d . . .
H12A H 1.0319 0.2484 0.5311 0.138 Uiso 1 1 calc R . .
H12B H 1.1683 0.2548 0.5411 0.138 Uiso 1 1 calc R . .
C13 C 1.1237(4) 0.1842(2) 0.6096(4) 0.0607(11) Uani 1 1 d . . .
H13 H 1.1116 0.1626 0.5422 0.073 Uiso 1 1 calc R . .
C14 C 1.2397(6) 0.1705(6) 0.6730(8) 0.217(7) Uani 1 1 d . . .
H14A H 1.2679 0.2005 0.7211 0.325 Uiso 1 1 calc R . .
H14B H 1.2932 0.1643 0.6248 0.325 Uiso 1 1 calc R . .
H14C H 1.2343 0.1378 0.7148 0.325 Uiso 1 1 calc R . .
C15 C 0.5249(3) 0.14381(15) 0.8716(3) 0.0449(9) Uani 1 1 d . . .
C16 C 0.5616(3) 0.17702(14) 0.7826(3) 0.0407(8) Uani 1 1 d . . .
C17 C 0.5463(4) 0.23299(15) 0.7870(3) 0.0470(9) Uani 1 1 d . . .
H17 H 0.5069 0.2464 0.8393 0.056 Uiso 1 1 calc R . .
C18 C 0.6095(3) 0.15464(14) 0.6966(3) 0.0384(8) Uani 1 1 d . . .
C19 C 0.6514(3) 0.19467(15) 0.6261(3) 0.0402(8) Uani 1 1 d . . .
C20 C 0.7108(3) 0.17588(17) 0.5460(3) 0.0481(9) Uani 1 1 d . . .
H20 H 0.7167 0.1384 0.5326 0.058 Uiso 1 1 calc R . .
C21 C 0.7596(4) 0.2139(2) 0.4884(3) 0.0602(11) Uani 1 1 d . . .
C22 C 0.7501(4) 0.2703(2) 0.5027(4) 0.0647(12) Uani 1 1 d . . .
H22 H 0.7853 0.2948 0.4617 0.078 Uiso 1 1 calc R . .
C23 C 0.6892(4) 0.28983(18) 0.5769(4) 0.0584(11) Uani 1 1 d . . .
C24 C 0.6402(3) 0.25155(15) 0.6407(3) 0.0463(9) Uani 1 1 d . . .
C25 C 0.6780(6) 0.3511(2) 0.5965(5) 0.0886(17) Uani 1 1 d . . .
H25A H 0.6118 0.3656 0.5444 0.106 Uiso 1 1 calc R . .
H25B H 0.7484 0.3697 0.5847 0.106 Uiso 1 1 calc R . .
C26 C 0.6600(6) 0.3635(2) 0.7125(5) 0.0919(18) Uani 1 1 d . . .
H26A H 0.7316 0.3551 0.7643 0.110 Uiso 1 1 calc R . .
H26B H 0.6429 0.4024 0.7188 0.110 Uiso 1 1 calc R . .
C27 C 0.5607(4) 0.32972(16) 0.7377(4) 0.0613(11) Uani 1 1 d . . .
H27 H 0.5593 0.3352 0.8148 0.074 Uiso 1 1 calc R . .
C28 C 0.4405(5) 0.3446(2) 0.6739(5) 0.0926(18) Uani 1 1 d . . .
H28A H 0.4419 0.3445 0.5976 0.139 Uiso 1 1 calc R . .
H28B H 0.4191 0.3807 0.6949 0.139 Uiso 1 1 calc R . .
H28C H 0.3840 0.3181 0.6884 0.139 Uiso 1 1 calc R . .
C29 C 0.4880(5) -0.0086(2) 0.6718(4) 0.0761(15) Uani 1 1 d . . .
H29 H 0.5181 0.0123 0.6214 0.091 Uiso 1 1 calc R . .
C30 C 0.3838(5) -0.0363(2) 0.6364(4) 0.0864(18) Uani 1 1 d . . .
H30 H 0.3438 -0.0340 0.5646 0.104 Uiso 1 1 calc R . .
C31 C 0.3414(4) -0.06739(19) 0.7117(4) 0.0697(13) Uani 1 1 d . . .
H31 H 0.2710 -0.0865 0.6910 0.084 Uiso 1 1 calc R . .
C32 C 0.4013(4) -0.07052(16) 0.8157(4) 0.0531(10) Uani 1 1 d . . .
H32 H 0.3725 -0.0915 0.8667 0.064 Uiso 1 1 calc R . .
C33 C 0.5072(3) -0.04164(14) 0.8449(3) 0.0423(8) Uani 1 1 d . . .
C34 C 0.6745(3) -0.02999(14) 1.0051(3) 0.0404(8) Uani 1 1 d . . .
C35 C 0.7137(4) -0.04977(16) 1.1114(3) 0.0551(10) Uani 1 1 d . . .
H35 H 0.6665 -0.0735 1.1423 0.066 Uiso 1 1 calc R . .
C36 C 0.8203(4) -0.03431(19) 1.1688(4) 0.0623(11) Uani 1 1 d . . .
H36 H 0.8460 -0.0464 1.2399 0.075 Uiso 1 1 calc R . .
C37 C 0.8897(4) -0.00052(18) 1.1205(4) 0.0667(13) Uani 1 1 d . . .
H37 H 0.9645 0.0096 1.1572 0.080 Uiso 1 1 calc R . .
C38 C 0.8473(4) 0.01779(18) 1.0185(4) 0.0616(11) Uani 1 1 d . . .
H38 H 0.8949 0.0408 0.9865 0.074 Uiso 1 1 calc R . .
O7A O 0.9560(6) 0.0664(2) 0.4061(4) 0.103(2) Uani 0.724(9) 1 d P A 1
O7B O 0.7772(18) -0.0782(6) 0.5127(17) 0.146(9) Uani 0.276(9) 1 d P A 2


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 2.023(3) . ?
Co1 O4 2.052(2) . ?
Co1 O3 2.097(2) . ?
Co1 N1 2.110(3) . ?
Co1 N2 2.112(3) . ?
Co1 O6 2.136(2) . ?
F1 C7 1.359(5) . ?
F2 C21 1.363(5) . ?
N1 C33 1.336(5) . ?
N1 C29 1.338(6) . ?
N2 C34 1.326(4) . ?
N2 C38 1.359(5) . ?
N3 C33 1.369(5) . ?
N3 C34 1.373(5) . ?
N3 H3A 0.8600 . ?
N4 C3 1.325(5) . ?
N4 C10 1.386(5) . ?
N4 C13 1.499(5) . ?
N5 C17 1.332(5) . ?
N5 C24 1.393(5) . ?
N5 C27 1.497(5) . ?
O1 C1 1.260(5) . ?
O2 C1 1.236(5) . ?
O3 C4 1.264(4) . ?
O4 C15 1.266(4) . ?
O5 C15 1.237(4) . ?
O6 C18 1.261(4) . ?
C1 C2 1.506(5) . ?
C2 C3 1.378(5) . ?
C2 C4 1.409(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.464(5) . ?
C5 C6 1.395(5) . ?
C5 C10 1.396(5) . ?
C6 C7 1.360(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.367(6) . ?
C8 C9 1.368(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.409(5) . ?
C9 C11 1.510(6) . ?
C11 C12 1.513(8) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.489(8) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.460(9) . ?
C13 H13 0.9800 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.504(5) . ?
C16 C17 1.371(5) . ?
C16 C18 1.416(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.459(5) . ?
C19 C24 1.400(5) . ?
C19 C20 1.401(5) . ?
C20 C21 1.362(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.386(6) . ?
C22 C23 1.360(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.415(5) . ?
C23 C25 1.514(7) . ?
C25 C26 1.540(8) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C27 1.497(7) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.508(7) . ?
C27 H27 0.9800 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C30 1.377(7) . ?
C29 H29 0.9300 . ?
C30 C31 1.373(7) . ?
C30 H30 0.9300 . ?
C31 C32 1.354(6) . ?
C31 H31 0.9300 . ?
C32 C33 1.398(5) . ?
C32 H32 0.9300 . ?
C34 C35 1.406(5) . ?
C35 C36 1.355(6) . ?
C35 H35 0.9300 . ?
C36 C37 1.370(6) . ?
C36 H36 0.9300 . ?
C37 C38 1.352(6) . ?
C37 H37 0.9300 . ?
C38 H38 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 173.55(10) . . ?
O1 Co1 O3 86.61(10) . . ?
O4 Co1 O3 90.27(10) . . ?
O1 Co1 N1 94.02(12) . . ?
O4 Co1 N1 89.11(12) . . ?
O3 Co1 N1 179.37(12) . . ?
O1 Co1 N2 93.67(12) . . ?
O4 Co1 N2 92.14(11) . . ?
O3 Co1 N2 93.27(11) . . ?
N1 Co1 N2 86.63(12) . . ?
O1 Co1 O6 88.47(11) . . ?
O4 Co1 O6 85.56(10) . . ?
O3 Co1 O6 83.27(10) . . ?
N1 Co1 O6 96.79(11) . . ?
N2 Co1 O6 175.83(11) . . ?
C33 N1 C29 117.3(4) . . ?
C33 N1 Co1 124.7(3) . . ?
C29 N1 Co1 116.6(3) . . ?
C34 N2 C38 117.1(3) . . ?
C34 N2 Co1 125.5(3) . . ?
C38 N2 Co1 116.5(2) . . ?
C33 N3 C34 133.4(3) . . ?
C33 N3 H3A 113.3 . . ?
C34 N3 H3A 113.3 . . ?
C3 N4 C10 119.9(3) . . ?
C3 N4 C13 119.5(3) . . ?
C10 N4 C13 120.6(3) . . ?
C17 N5 C24 119.5(3) . . ?
C17 N5 C27 119.0(3) . . ?
C24 N5 C27 121.5(3) . . ?
C1 O1 Co1 126.4(2) . . ?
C4 O3 Co1 121.9(2) . . ?
C15 O4 Co1 130.1(2) . . ?
C18 O6 Co1 118.7(2) . . ?
O2 C1 O1 123.6(4) . . ?
O2 C1 C2 117.2(4) . . ?
O1 C1 C2 119.2(3) . . ?
C3 C2 C4 118.2(3) . . ?
C3 C2 C1 116.4(3) . . ?
C4 C2 C1 125.4(3) . . ?
N4 C3 C2 125.4(4) . . ?
N4 C3 H3 117.3 . . ?
C2 C3 H3 117.3 . . ?
O3 C4 C2 125.7(3) . . ?
O3 C4 C5 118.0(3) . . ?
C2 C4 C5 116.2(3) . . ?
C6 C5 C10 119.5(3) . . ?
C6 C5 C4 119.1(3) . . ?
C10 C5 C4 121.3(3) . . ?
C7 C6 C5 118.4(4) . . ?
C7 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
F1 C7 C6 119.2(4) . . ?
F1 C7 C8 117.9(4) . . ?
C6 C7 C8 122.9(4) . . ?
C7 C8 C9 120.3(4) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C10 118.5(4) . . ?
C8 C9 C11 121.9(4) . . ?
C10 C9 C11 119.6(4) . . ?
N4 C10 C5 118.4(3) . . ?
N4 C10 C9 121.1(3) . . ?
C5 C10 C9 120.4(4) . . ?
C9 C11 C12 111.8(4) . . ?
C9 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
C9 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C11 111.9(5) . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C12 114.4(7) . . ?
C14 C13 N4 109.7(4) . . ?
C12 C13 N4 108.6(4) . . ?
C14 C13 H13 108.0 . . ?
C12 C13 H13 108.0 . . ?
N4 C13 H13 108.0 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O5 C15 O4 122.6(3) . . ?
O5 C15 C16 118.3(3) . . ?
O4 C15 C16 119.1(3) . . ?
C17 C16 C18 118.8(3) . . ?
C17 C16 C15 116.3(3) . . ?
C18 C16 C15 124.9(3) . . ?
N5 C17 C16 125.3(4) . . ?
N5 C17 H17 117.3 . . ?
C16 C17 H17 117.3 . . ?
O6 C18 C16 124.8(3) . . ?
O6 C18 C19 119.3(3) . . ?
C16 C18 C19 115.8(3) . . ?
C24 C19 C20 119.0(3) . . ?
C24 C19 C18 121.7(3) . . ?
C20 C19 C18 119.2(3) . . ?
C21 C20 C19 118.4(4) . . ?
C21 C20 H20 120.8 . . ?
C19 C20 H20 120.8 . . ?
C20 C21 F2 118.5(4) . . ?
C20 C21 C22 123.1(4) . . ?
F2 C21 C22 118.3(4) . . ?
C23 C22 C21 119.8(4) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C24 118.7(4) . . ?
C22 C23 C25 121.7(4) . . ?
C24 C23 C25 119.6(4) . . ?
N5 C24 C19 118.5(3) . . ?
N5 C24 C23 120.6(4) . . ?
C19 C24 C23 120.9(4) . . ?
C23 C25 C26 112.1(4) . . ?
C23 C25 H25A 109.2 . . ?
C26 C25 H25A 109.2 . . ?
C23 C25 H25B 109.2 . . ?
C26 C25 H25B 109.2 . . ?
H25A C25 H25B 107.9 . . ?
C27 C26 C25 110.3(5) . . ?
C27 C26 H26A 109.6 . . ?
C25 C26 H26A 109.6 . . ?
C27 C26 H26B 109.6 . . ?
C25 C26 H26B 109.6 . . ?
H26A C26 H26B 108.1 . . ?
C26 C27 N5 110.0(4) . . ?
C26 C27 C28 115.2(4) . . ?
N5 C27 C28 109.3(4) . . ?
C26 C27 H27 107.3 . . ?
N5 C27 H27 107.3 . . ?
C28 C27 H27 107.3 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N1 C29 C30 124.2(4) . . ?
N1 C29 H29 117.9 . . ?
C30 C29 H29 117.9 . . ?
C31 C30 C29 117.1(5) . . ?
C31 C30 H30 121.4 . . ?
C29 C30 H30 121.4 . . ?
C32 C31 C30 120.6(4) . . ?
C32 C31 H31 119.7 . . ?
C30 C31 H31 119.7 . . ?
C31 C32 C33 118.8(4) . . ?
C31 C32 H32 120.6 . . ?
C33 C32 H32 120.6 . . ?
N1 C33 N3 121.4(3) . . ?
N1 C33 C32 122.0(4) . . ?
N3 C33 C32 116.6(3) . . ?
N2 C34 N3 121.2(3) . . ?
N2 C34 C35 121.1(4) . . ?
N3 C34 C35 117.7(3) . . ?
C36 C35 C34 120.0(4) . . ?
C36 C35 H35 120.0 . . ?
C34 C35 H35 120.0 . . ?
C35 C36 C37 119.0(4) . . ?
C35 C36 H36 120.5 . . ?
C37 C36 H36 120.5 . . ?
C38 C37 C36 118.6(4) . . ?
C38 C37 H37 120.7 . . ?
C36 C37 H37 120.7 . . ?
C37 C38 N2 124.0(4) . . ?
C37 C38 H38 118.0 . . ?
N2 C38 H38 118.0 . . ?

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
O1 Co1 N1 C33 119.7(3) . . . . ?
O4 Co1 N1 C33 -65.9(3) . . . . ?
N2 Co1 N1 C33 26.3(3) . . . . ?
O6 Co1 N1 C33 -151.3(3) . . . . ?
O1 Co1 N1 C29 -74.3(4) . . . . ?
O4 Co1 N1 C29 100.1(4) . . . . ?
N2 Co1 N1 C29 -167.7(4) . . . . ?
O6 Co1 N1 C29 14.7(4) . . . . ?
O1 Co1 N2 C34 -118.5(3) . . . . ?
O4 Co1 N2 C34 64.3(3) . . . . ?
O3 Co1 N2 C34 154.7(3) . . . . ?
N1 Co1 N2 C34 -24.7(3) . . . . ?
O1 Co1 N2 C38 72.2(3) . . . . ?
O4 Co1 N2 C38 -105.0(3) . . . . ?
O3 Co1 N2 C38 -14.6(3) . . . . ?
N1 Co1 N2 C38 166.0(3) . . . . ?
O3 Co1 O1 C1 -40.2(3) . . . . ?
N1 Co1 O1 C1 139.8(3) . . . . ?
N2 Co1 O1 C1 -133.3(3) . . . . ?
O6 Co1 O1 C1 43.1(3) . . . . ?
O1 Co1 O3 C4 34.6(3) . . . . ?
O4 Co1 O3 C4 -139.7(3) . . . . ?
N2 Co1 O3 C4 128.1(3) . . . . ?
O6 Co1 O3 C4 -54.2(3) . . . . ?
O3 Co1 O4 C15 58.8(3) . . . . ?
N1 Co1 O4 C15 -121.3(3) . . . . ?
N2 Co1 O4 C15 152.1(3) . . . . ?
O6 Co1 O4 C15 -24.5(3) . . . . ?
O1 Co1 O6 C18 -135.3(3) . . . . ?
O4 Co1 O6 C18 42.2(3) . . . . ?
O3 Co1 O6 C18 -48.6(3) . . . . ?
N1 Co1 O6 C18 130.8(3) . . . . ?
Co1 O1 C1 O2 -148.8(4) . . . . ?
Co1 O1 C1 C2 32.9(5) . . . . ?
O2 C1 C2 C3 -5.8(6) . . . . ?
O1 C1 C2 C3 172.7(4) . . . . ?
O2 C1 C2 C4 174.5(4) . . . . ?
O1 C1 C2 C4 -7.1(6) . . . . ?
C10 N4 C3 C2 -3.0(6) . . . . ?
C13 N4 C3 C2 175.4(4) . . . . ?
C4 C2 C3 N4 -4.0(6) . . . . ?
C1 C2 C3 N4 176.2(4) . . . . ?
Co1 O3 C4 C2 -25.2(5) . . . . ?
Co1 O3 C4 C5 152.2(2) . . . . ?
C3 C2 C4 O3 -175.2(3) . . . . ?
C1 C2 C4 O3 4.6(6) . . . . ?
C3 C2 C4 C5 7.3(5) . . . . ?
C1 C2 C4 C5 -172.9(3) . . . . ?
O3 C4 C5 C6 -5.9(5) . . . . ?
C2 C4 C5 C6 171.8(3) . . . . ?
O3 C4 C5 C10 177.8(3) . . . . ?
C2 C4 C5 C10 -4.5(5) . . . . ?
C10 C5 C6 C7 0.0(6) . . . . ?
C4 C5 C6 C7 -176.3(4) . . . . ?
C5 C6 C7 F1 179.6(4) . . . . ?
C5 C6 C7 C8 1.3(7) . . . . ?
F1 C7 C8 C9 -179.8(4) . . . . ?
C6 C7 C8 C9 -1.4(7) . . . . ?
C7 C8 C9 C10 0.2(7) . . . . ?
C7 C8 C9 C11 -179.7(5) . . . . ?
C3 N4 C10 C5 5.9(5) . . . . ?
C13 N4 C10 C5 -172.5(3) . . . . ?
C3 N4 C10 C9 -171.3(4) . . . . ?
C13 N4 C10 C9 10.3(6) . . . . ?
C6 C5 C10 N4 -178.4(3) . . . . ?
C4 C5 C10 N4 -2.1(5) . . . . ?
C6 C5 C10 C9 -1.2(6) . . . . ?
C4 C5 C10 C9 175.1(4) . . . . ?
C8 C9 C10 N4 178.2(4) . . . . ?
C11 C9 C10 N4 -1.8(7) . . . . ?
C8 C9 C10 C5 1.1(6) . . . . ?
C11 C9 C10 C5 -179.0(4) . . . . ?
C8 C9 C11 C12 -158.0(6) . . . . ?
C10 C9 C11 C12 22.0(8) . . . . ?
C9 C11 C12 C13 -50.9(8) . . . . ?
C11 C12 C13 C14 -65.3(7) . . . . ?
C11 C12 C13 N4 57.6(7) . . . . ?
C3 N4 C13 C14 -90.6(8) . . . . ?
C10 N4 C13 C14 87.8(8) . . . . ?
C3 N4 C13 C12 143.6(5) . . . . ?
C10 N4 C13 C12 -38.0(6) . . . . ?
Co1 O4 C15 O5 -178.7(3) . . . . ?
Co1 O4 C15 C16 1.1(5) . . . . ?
O5 C15 C16 C17 18.8(6) . . . . ?
O4 C15 C16 C17 -161.0(4) . . . . ?
O5 C15 C16 C18 -161.0(4) . . . . ?
O4 C15 C16 C18 19.2(6) . . . . ?
C24 N5 C17 C16 1.6(6) . . . . ?
C27 N5 C17 C16 -179.5(4) . . . . ?
C18 C16 C17 N5 -6.9(6) . . . . ?
C15 C16 C17 N5 173.3(4) . . . . ?
Co1 O6 C18 C16 -39.6(5) . . . . ?
Co1 O6 C18 C19 137.2(3) . . . . ?
C17 C16 C18 O6 -176.2(4) . . . . ?
C15 C16 C18 O6 3.6(6) . . . . ?
C17 C16 C18 C19 6.9(5) . . . . ?
C15 C16 C18 C19 -173.3(3) . . . . ?
O6 C18 C19 C24 -179.5(3) . . . . ?
C16 C18 C19 C24 -2.5(5) . . . . ?
O6 C18 C19 C20 -3.5(5) . . . . ?
C16 C18 C19 C20 173.6(3) . . . . ?
C24 C19 C20 C21 2.6(6) . . . . ?
C18 C19 C20 C21 -173.5(4) . . . . ?
C19 C20 C21 F2 178.3(3) . . . . ?
C19 C20 C21 C22 -2.1(7) . . . . ?
C20 C21 C22 C23 -0.3(7) . . . . ?
F2 C21 C22 C23 179.3(4) . . . . ?
C21 C22 C23 C24 2.2(7) . . . . ?
C21 C22 C23 C25 179.1(5) . . . . ?
C17 N5 C24 C19 3.1(6) . . . . ?
C27 N5 C24 C19 -175.7(4) . . . . ?
C17 N5 C24 C23 -174.6(4) . . . . ?
C27 N5 C24 C23 6.6(6) . . . . ?
C20 C19 C24 N5 -178.5(3) . . . . ?
C18 C19 C24 N5 -2.5(6) . . . . ?
C20 C19 C24 C23 -0.9(6) . . . . ?
C18 C19 C24 C23 175.2(4) . . . . ?
C22 C23 C24 N5 176.1(4) . . . . ?
C25 C23 C24 N5 -1.0(7) . . . . ?
C22 C23 C24 C19 -1.6(6) . . . . ?
C25 C23 C24 C19 -178.6(4) . . . . ?
C22 C23 C25 C26 -153.0(5) . . . . ?
C24 C23 C25 C26 23.9(7) . . . . ?
C23 C25 C26 C27 -51.8(7) . . . . ?
C25 C26 C27 N5 56.2(6) . . . . ?
C25 C26 C27 C28 -67.9(6) . . . . ?
C17 N5 C27 C26 146.2(4) . . . . ?
C24 N5 C27 C26 -35.0(6) . . . . ?
C17 N5 C27 C28 -86.4(5) . . . . ?
C24 N5 C27 C28 92.5(5) . . . . ?
C33 N1 C29 C30 2.7(8) . . . . ?
Co1 N1 C29 C30 -164.4(5) . . . . ?
N1 C29 C30 C31 -0.8(9) . . . . ?
C29 C30 C31 C32 -0.5(9) . . . . ?
C30 C31 C32 C33 -0.2(7) . . . . ?
C29 N1 C33 N3 176.8(4) . . . . ?
Co1 N1 C33 N3 -17.3(5) . . . . ?
C29 N1 C33 C32 -3.4(6) . . . . ?
Co1 N1 C33 C32 162.6(3) . . . . ?
C34 N3 C33 N1 -6.3(6) . . . . ?
C34 N3 C33 C32 173.8(4) . . . . ?
C31 C32 C33 N1 2.2(6) . . . . ?
C31 C32 C33 N3 -177.9(4) . . . . ?
C38 N2 C34 N3 -177.0(4) . . . . ?
Co1 N2 C34 N3 13.8(5) . . . . ?
C38 N2 C34 C35 3.4(5) . . . . ?
Co1 N2 C34 C35 -165.8(3) . . . . ?
C33 N3 C34 N2 8.3(6) . . . . ?
C33 N3 C34 C35 -172.2(4) . . . . ?
N2 C34 C35 C36 -1.3(6) . . . . ?
N3 C34 C35 C36 179.2(4) . . . . ?
C34 C35 C36 C37 -1.7(7) . . . . ?
C35 C36 C37 C38 2.4(7) . . . . ?
C36 C37 C38 N2 -0.1(8) . . . . ?
C34 N2 C38 C37 -2.8(6) . . . . ?
Co1 N2 C38 C37 167.4(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3A O4 0.86 2.14 2.980(4) 167.0 3_657

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.993
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.070
