# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

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

data_akhCEJ1
_database_code_depnum_ccdc_archive 'CCDC 1008427'
_audit_update_record             
;
2014-06-15 deposited with the CCDC.
2015-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H23 Co F12 N4 O2 P2'
_chemical_formula_sum            'C32 H29 Co F12 N4 O3 P2'
_chemical_formula_weight         857.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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

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

_cell_length_a                   10.9653(9)
_cell_length_b                   12.3019(10)
_cell_length_c                   14.4805(11)
_cell_angle_alpha                95.630(4)
_cell_angle_beta                 92.362(4)
_cell_angle_gamma                113.716(4)
_cell_volume                     1772.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Brown
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             812
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8243
_exptl_absorpt_correction_T_max  0.9360
_exptl_absorpt_process_details   SADABS(Sheldrick,1997)

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart CCD Area Detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 0.3
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            46443
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.42
_diffrn_reflns_theta_max         27.00
_reflns_number_total             7678
_reflns_number_gt                6691
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker Smart'
_computing_cell_refinement       'Bruker Smart'
_computing_data_reduction        'Bruker Saint'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.1440P)²+1.8460P] 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         7678
_refine_ls_number_parameters     489
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0701
_refine_ls_wR_factor_ref         0.2205
_refine_ls_wR_factor_gt          0.2094
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.041
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.23102(4) 0.20690(4) 0.27674(3) 0.03027(17) Uani 1 1 d . . .
P1 P -0.28368(10) 0.16900(11) 0.28627(8) 0.0546(3) Uani 1 1 d . . .
P2 P 0.0999(2) 0.66882(14) 0.26452(10) 0.0811(5) Uani 1 1 d . . .
O1 O 0.0633(2) 0.0813(2) 0.28362(16) 0.0382(5) Uani 1 1 d . . .
O2 O 0.3232(2) 0.1611(2) 0.36694(16) 0.0376(5) Uani 1 1 d . . .
N2 N 0.4007(3) 0.3449(2) 0.27292(19) 0.0353(6) Uani 1 1 d . . .
N3 N 0.1450(3) 0.2540(2) 0.17669(18) 0.0343(6) Uani 1 1 d . . .
N1 N 0.1975(3) 0.3120(3) 0.37159(18) 0.0357(6) Uani 1 1 d . . .
N4 N 0.2662(3) 0.1090(3) 0.1767(2) 0.0369(6) Uani 1 1 d . . .
C12 C 0.3016(3) 0.4202(3) 0.3900(2) 0.0383(7) Uani 1 1 d . . .
F2 F -0.1743(4) 0.1364(4) 0.2364(3) 0.1017(12) Uani 1 1 d . . .
F5 F -0.1820(4) 0.3052(3) 0.2983(3) 0.1059(12) Uani 1 1 d . . .
C10 C 0.5039(4) 0.3548(4) 0.2248(3) 0.0469(8) Uani 1 1 d . . .
H10 H 0.4966 0.2919 0.1806 0.056 Uiso 1 1 calc R . .
C11 C 0.4135(3) 0.4381(3) 0.3373(2) 0.0393(7) Uani 1 1 d . . .
F3 F -0.3416(4) 0.1834(5) 0.1879(2) 0.1113(15) Uani 1 1 d . . .
C1 C 0.0892(4) 0.2910(4) 0.4180(2) 0.0455(8) Uani 1 1 d . . .
H1 H 0.0165 0.2174 0.4050 0.055 Uiso 1 1 calc R . .
F4 F -0.3907(4) 0.2072(5) 0.3339(3) 0.1112(14) Uani 1 1 d . . .
C4 C 0.3030(5) 0.5109(4) 0.4572(3) 0.0524(9) Uani 1 1 d . . .
C29 C 0.3669(5) 0.0428(4) 0.4698(3) 0.0582(10) Uani 1 1 d . . .
H29C H 0.4559 0.1018 0.4668 0.087 Uiso 1 1 calc R . .
H29A H 0.3626 -0.0350 0.4481 0.087 Uiso 1 1 calc R . .
H29B H 0.3440 0.0445 0.5331 0.087 Uiso 1 1 calc R . .
C16 C 0.0837(4) 0.2057(4) 0.0099(3) 0.0508(9) Uani 1 1 d . . .
C28 C 0.2699(3) 0.0698(3) 0.4094(2) 0.0387(7) Uani 1 1 d . . .
C7 C 0.5282(4) 0.5439(4) 0.3541(3) 0.0524(9) Uani 1 1 d . . .
F6 F -0.2246(4) 0.1533(5) 0.3825(3) 0.1154(15) Uani 1 1 d . . .
C25 C -0.1026(4) -0.0836(3) 0.3375(3) 0.0486(8) Uani 1 1 d . . .
H25A H -0.1553 -0.0663 0.2913 0.073 Uiso 1 1 calc R . .
H25C H -0.1356 -0.0774 0.3973 0.073 Uiso 1 1 calc R . .
H25B H -0.1085 -0.1633 0.3217 0.073 Uiso 1 1 calc R . .
C15 C 0.0178(5) 0.2831(4) 0.0164(3) 0.0586(10) Uani 1 1 d . . .
H15 H -0.0245 0.2943 -0.0366 0.070 Uiso 1 1 calc R . .
C23 C 0.2125(3) 0.1161(3) 0.0926(2) 0.0390(7) Uani 1 1 d . . .
C2 C 0.0828(5) 0.3766(5) 0.4853(3) 0.0573(11) Uani 1 1 d . . .
H2 H 0.0063 0.3598 0.5169 0.079(17) Uiso 1 1 calc R . .
C27 C 0.1352(4) -0.0044(4) 0.4029(3) 0.0486(9) Uani 1 1 d . . .
H27 H 0.1064 -0.0634 0.4423 0.058 Uiso 1 1 calc R . .
C22 C 0.3307(4) 0.0389(3) 0.1804(3) 0.0456(8) Uani 1 1 d . . .
H22 H 0.3679 0.0334 0.2377 0.055 Uiso 1 1 calc R . .
C9 C 0.6233(4) 0.4573(4) 0.2389(4) 0.0605(11) Uani 1 1 d . . .
H9 H 0.6945 0.4616 0.2044 0.073 Uiso 1 1 calc R . .
C13 C 0.0816(4) 0.3255(3) 0.1808(3) 0.0442(8) Uani 1 1 d . . .
H13 H 0.0802 0.3662 0.2380 0.053 Uiso 1 1 calc R . .
C26 C 0.0406(3) 0.0042(3) 0.3410(2) 0.0375(7) Uani 1 1 d . . .
C24 C 0.1458(3) 0.1946(3) 0.0924(2) 0.0392(7) Uani 1 1 d . . .
C19 C 0.2184(4) 0.0507(4) 0.0093(3) 0.0516(9) Uani 1 1 d . . .
F1 F -0.3851(5) 0.0352(4) 0.2754(5) 0.152(2) Uani 1 1 d . . .
C8 C 0.6362(4) 0.5508(4) 0.3026(4) 0.0627(11) Uani 1 1 d . . .
H7 H 0.7160 0.6189 0.3120 0.075 Uiso 1 1 calc R . .
F10 F 0.0216(14) 0.5975(6) 0.1732(5) 0.265(6) Uani 1 1 d . . .
C5 C 0.4216(6) 0.6196(4) 0.4721(4) 0.0702(13) Uani 1 1 d . . .
H5 H 0.4248 0.6816 0.5158 0.084 Uiso 1 1 calc R . .
F7 F -0.0145(8) 0.6986(8) 0.3010(7) 0.220(4) Uani 1 1 d . . .
C3 C 0.1888(5) 0.4862(4) 0.5055(3) 0.0596(11) Uani 1 1 d . . .
H3 H 0.1847 0.5435 0.5508 0.072 Uiso 1 1 calc R . .
C17 C 0.0884(5) 0.1363(5) -0.0738(3) 0.0653(12) Uani 1 1 d . . .
H17 H 0.0461 0.1414 -0.1292 0.071(15) Uiso 1 1 calc R . .
C20 C 0.2888(5) -0.0219(4) 0.0162(3) 0.0588(11) Uani 1 1 d . . .
H20 H 0.2974 -0.0665 -0.0368 0.071 Uiso 1 1 calc R . .
F9 F 0.2045(10) 0.6226(10) 0.2399(10) 0.320(8) Uani 1 1 d . . .
C14 C 0.0163(5) 0.3416(4) 0.1012(3) 0.0576(10) Uani 1 1 d . . .
H14 H -0.0279 0.3923 0.1062 0.069 Uiso 1 1 calc R . .
C21 C 0.3444(5) -0.0271(4) 0.1006(3) 0.0584(10) Uani 1 1 d . . .
H21 H 0.3916 -0.0748 0.1050 0.070 Uiso 1 1 calc R . .
C6 C 0.5293(5) 0.6342(4) 0.4240(4) 0.0692(13) Uani 1 1 d . . .
H6 H 0.6059 0.7049 0.4371 0.083 Uiso 1 1 calc R . .
F8 F 0.0397(10) 0.5498(5) 0.3084(4) 0.194(3) Uani 1 1 d . . .
C18 C 0.1532(6) 0.0631(5) -0.0739(3) 0.0675(13) Uani 1 1 d . . .
H18 H 0.1553 0.0197 -0.1296 0.081 Uiso 1 1 calc R . .
F11 F 0.1702(8) 0.7316(5) 0.3610(4) 0.170(3) Uani 1 1 d . . .
O3 O 0.4774(17) 0.3002(19) 0.0107(8) 0.184(10) Uani 0.43 1 d P . .
F12 F 0.1403(15) 0.7846(5) 0.2243(5) 0.316(8) Uani 1 1 d . . .
C31 C 0.5498(18) 0.320(2) -0.0387(16) 0.247(12) Uani 1 1 d . . .
C32 C 0.4920(16) 0.276(2) -0.1454(18) 0.263(12) Uani 1 1 d . . .
H32A H 0.4045 0.2119 -0.1486 0.395 Uiso 1 1 calc R . .
H32B H 0.5503 0.2474 -0.1779 0.395 Uiso 1 1 calc R . .
H32C H 0.4866 0.3411 -0.1737 0.395 Uiso 1 1 calc R . .
C30 C 0.670(3) 0.415(3) -0.033(2) 0.62(4) Uani 1 1 d . . .
H30A H 0.7020 0.4441 0.0308 0.936 Uiso 1 1 calc R . .
H30B H 0.6592 0.4779 -0.0632 0.936 Uiso 1 1 calc R . .
H30C H 0.7329 0.3919 -0.0641 0.936 Uiso 1 1 calc R . .


_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 1.881(2) . ?
Co1 O1 1.881(2) . ?
Co1 N1 1.941(3) . ?
Co1 N4 1.943(3) . ?
Co1 N3 1.953(3) . ?
Co1 N2 1.958(3) . ?
P1 F1 1.560(4) . ?
P1 F6 1.574(4) . ?
P1 F5 1.582(4) . ?
P1 F4 1.587(3) . ?
P1 F2 1.588(3) . ?
P1 F3 1.590(4) . ?
P2 F12 1.497(6) . ?
P2 F9 1.511(8) . ?
P2 F10 1.526(6) . ?
P2 F11 1.538(5) . ?
P2 F7 1.541(7) . ?
P2 F8 1.557(6) . ?
O1 C26 1.278(4) . ?
O2 C28 1.273(4) . ?
N2 C10 1.323(5) . ?
N2 C11 1.362(4) . ?
N3 C13 1.321(5) . ?
N3 C24 1.361(4) . ?
N1 C1 1.335(5) . ?
N1 C12 1.353(5) . ?
N4 C22 1.320(5) . ?
N4 C23 1.358(4) . ?
C12 C4 1.401(5) . ?
C12 C11 1.424(5) . ?
C10 C9 1.394(6) . ?
C11 C7 1.390(5) . ?
C1 C2 1.389(6) . ?
C4 C3 1.398(7) . ?
C4 C5 1.431(7) . ?
C29 C28 1.506(5) . ?
C16 C24 1.397(5) . ?
C16 C15 1.407(6) . ?
C16 C17 1.428(6) . ?
C28 C27 1.382(5) . ?
C7 C8 1.403(7) . ?
C7 C6 1.424(7) . ?
C25 C26 1.500(5) . ?
C15 C14 1.365(6) . ?
C23 C19 1.402(5) . ?
C23 C24 1.427(5) . ?
C2 C3 1.374(7) . ?
C27 C26 1.386(5) . ?
C22 C21 1.395(6) . ?
C9 C8 1.358(7) . ?
C13 C14 1.405(5) . ?
C19 C20 1.403(7) . ?
C19 C18 1.428(6) . ?
C5 C6 1.353(8) . ?
C17 C18 1.352(7) . ?
C20 C21 1.361(7) . ?
O3 C31 1.06(2) . ?
C31 C30 1.36(3) . ?
C31 C32 1.60(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Co1 O1 95.65(10) . . ?
O2 Co1 N1 90.65(11) . . ?
O1 Co1 N1 92.45(11) . . ?
O2 Co1 N4 92.06(11) . . ?
O1 Co1 N4 89.42(11) . . ?
N1 Co1 N4 176.54(12) . . ?
O2 Co1 N3 175.74(10) . . ?
O1 Co1 N3 86.80(11) . . ?
N1 Co1 N3 92.73(11) . . ?
N4 Co1 N3 84.46(12) . . ?
O2 Co1 N2 85.89(11) . . ?
O1 Co1 N2 176.24(11) . . ?
N1 Co1 N2 84.09(12) . . ?
N4 Co1 N2 93.96(12) . . ?
N3 Co1 N2 91.88(12) . . ?
F1 P1 F6 89.8(3) . . ?
F1 P1 F5 179.2(3) . . ?
F6 P1 F5 90.1(3) . . ?
F1 P1 F4 90.0(3) . . ?
F6 P1 F4 92.5(2) . . ?
F5 P1 F4 89.2(3) . . ?
F1 P1 F2 92.2(3) . . ?
F6 P1 F2 89.1(2) . . ?
F5 P1 F2 88.6(2) . . ?
F4 P1 F2 177.3(3) . . ?
F1 P1 F3 90.0(3) . . ?
F6 P1 F3 178.7(2) . . ?
F5 P1 F3 90.2(3) . . ?
F4 P1 F3 88.8(2) . . ?
F2 P1 F3 89.6(2) . . ?
F12 P2 F9 105.4(8) . . ?
F12 P2 F10 91.8(5) . . ?
F9 P2 F10 86.5(6) . . ?
F12 P2 F11 92.7(4) . . ?
F9 P2 F11 94.6(6) . . ?
F10 P2 F11 174.8(5) . . ?
F12 P2 F7 84.5(6) . . ?
F9 P2 F7 169.9(7) . . ?
F10 P2 F7 95.2(6) . . ?
F11 P2 F7 82.8(5) . . ?
F12 P2 F8 172.2(7) . . ?
F9 P2 F8 82.2(6) . . ?
F10 P2 F8 87.0(4) . . ?
F11 P2 F8 88.1(4) . . ?
F7 P2 F8 87.9(5) . . ?
C26 O1 Co1 124.2(2) . . ?
C28 O2 Co1 124.5(2) . . ?
C10 N2 C11 118.2(3) . . ?
C10 N2 Co1 129.8(3) . . ?
C11 N2 Co1 111.6(2) . . ?
C13 N3 C24 118.3(3) . . ?
C13 N3 Co1 129.9(2) . . ?
C24 N3 Co1 111.5(2) . . ?
C1 N1 C12 118.6(3) . . ?
C1 N1 Co1 129.1(3) . . ?
C12 N1 Co1 112.3(2) . . ?
C22 N4 C23 118.5(3) . . ?
C22 N4 Co1 129.6(3) . . ?
C23 N4 Co1 111.9(2) . . ?
N1 C12 C4 123.3(3) . . ?
N1 C12 C11 116.1(3) . . ?
C4 C12 C11 120.6(3) . . ?
N2 C10 C9 121.6(4) . . ?
N2 C11 C7 123.5(3) . . ?
N2 C11 C12 115.7(3) . . ?
C7 C11 C12 120.7(3) . . ?
N1 C1 C2 121.5(4) . . ?
C3 C4 C12 117.0(4) . . ?
C3 C4 C5 125.5(4) . . ?
C12 C4 C5 117.5(4) . . ?
C24 C16 C15 116.9(4) . . ?
C24 C16 C17 118.3(4) . . ?
C15 C16 C17 124.8(4) . . ?
O2 C28 C27 125.7(3) . . ?
O2 C28 C29 114.8(3) . . ?
C27 C28 C29 119.5(3) . . ?
C11 C7 C8 116.7(4) . . ?
C11 C7 C6 118.0(4) . . ?
C8 C7 C6 125.2(4) . . ?
C14 C15 C16 119.4(4) . . ?
N4 C23 C19 123.7(4) . . ?
N4 C23 C24 116.1(3) . . ?
C19 C23 C24 120.2(3) . . ?
C3 C2 C1 120.3(4) . . ?
C28 C27 C26 123.8(3) . . ?
N4 C22 C21 121.7(4) . . ?
C8 C9 C10 120.4(4) . . ?
N3 C13 C14 121.9(4) . . ?
O1 C26 C27 125.8(3) . . ?
O1 C26 C25 114.8(3) . . ?
C27 C26 C25 119.4(3) . . ?
N3 C24 C16 123.5(3) . . ?
N3 C24 C23 115.9(3) . . ?
C16 C24 C23 120.6(3) . . ?
C23 C19 C20 116.0(4) . . ?
C23 C19 C18 117.9(4) . . ?
C20 C19 C18 126.1(4) . . ?
C9 C8 C7 119.5(4) . . ?
C6 C5 C4 121.5(4) . . ?
C2 C3 C4 119.4(4) . . ?
C18 C17 C16 121.1(4) . . ?
C21 C20 C19 120.0(4) . . ?
C15 C14 C13 120.0(4) . . ?
C20 C21 C22 120.2(4) . . ?
C5 C6 C7 121.6(4) . . ?
C17 C18 C19 121.8(4) . . ?
O3 C31 C30 127.8(19) . . ?
O3 C31 C32 115.7(18) . . ?
C30 C31 C32 110(2) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.314
_refine_diff_density_min         -0.907
_refine_diff_density_rms         0.183
####################################################################### 
# 
# 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_akh_CC
_database_code_depnum_ccdc_archive 'CCDC 1008428'
_audit_update_record             
;
2014-07-16 deposited with the CCDC.
2015-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H23 Cl2 Co N8 O10'
_chemical_formula_sum            'C33 H23 Cl2 Co N8 O10'
_chemical_formula_weight         821.42

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'
Cl Cl 0.1484 0.1585 '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   P21/n

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                   12.736(5)
_cell_length_b                   15.757(5)
_cell_length_c                   17.209(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 95.701(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     3436(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            Brown
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1672
_exptl_absorpt_coefficient_mu    0.727
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8115
_exptl_absorpt_correction_T_max  0.9309
_exptl_absorpt_process_details   SADABS(Sheldrick,1997)

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart CCD Area Detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 0.3
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            62897
_diffrn_reflns_av_R_equivalents  0.0844
_diffrn_reflns_av_sigmaI/netI    0.0617
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         28.00
_reflns_number_total             8288
_reflns_number_gt                4725
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker Smart'
_computing_cell_refinement       'Bruker Smart'
_computing_data_reduction        'Bruker Saint'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.1535P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8288
_refine_ls_number_parameters     496
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1336
_refine_ls_R_factor_gt           0.0746
_refine_ls_wR_factor_ref         0.2549
_refine_ls_wR_factor_gt          0.2245
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.002
_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 0.26125(4) 0.12632(3) 0.16848(3) 0.0408(2) Uani 1 1 d . . .
Cl2 Cl 0.01514(11) 0.32434(10) 0.38806(9) 0.0749(4) Uani 1 1 d . . .
Cl1 Cl 0.3972(3) 0.17163(16) 0.48100(16) 0.1362(9) Uani 1 1 d . . .
O2 O 0.2434(2) 0.20754(17) 0.08770(17) 0.0504(7) Uani 1 1 d . . .
O1 O 0.2203(2) 0.03083(17) 0.10590(16) 0.0485(7) Uani 1 1 d . . .
N8 N 0.6227(3) 0.3919(2) 0.2899(2) 0.0525(9) Uani 1 1 d . . .
N2 N 0.1167(3) 0.1343(2) 0.1930(2) 0.0438(8) Uani 1 1 d . . .
N3 N 0.4080(3) 0.1193(2) 0.1483(2) 0.0431(8) Uani 1 1 d . . .
N4 N 0.3100(3) 0.2213(2) 0.23474(18) 0.0402(7) Uani 1 1 d . . .
N1 N 0.2766(3) 0.0481(2) 0.2563(2) 0.0469(8) Uani 1 1 d . . .
C19 C 0.6256(3) 0.2700(3) 0.2064(3) 0.0492(10) Uani 1 1 d . . .
C22 C 0.5722(3) 0.3256(3) 0.2535(2) 0.0439(10) Uani 1 1 d . . .
C13 C 0.0967(3) 0.0842(3) 0.2531(2) 0.0462(10) Uani 1 1 d . . .
C24 C 0.4043(4) 0.3599(3) 0.3124(3) 0.0463(10) Uani 1 1 d . . .
H24 H 0.4357 0.4057 0.3397 0.056 Uiso 1 1 calc R . .
N7 N 0.7279(3) 0.2835(3) 0.1951(3) 0.0668(12) Uani 1 1 d . . .
C18 C 0.5717(3) 0.1984(3) 0.1683(2) 0.0487(10) Uani 1 1 d . . .
C23 C 0.4621(3) 0.3110(2) 0.2649(2) 0.0397(9) Uani 1 1 d . . .
C28 C 0.4660(3) 0.1856(3) 0.1794(2) 0.0425(9) Uani 1 1 d . . .
C26 C 0.2554(3) 0.2699(3) 0.2809(2) 0.0467(10) Uani 1 1 d . . .
H26 H 0.1859 0.2557 0.2874 0.056 Uiso 1 1 calc R . .
32 C 0.2175(4) 0.1895(3) 0.0157(3) 0.0498(10) Uani 1 1 d . . .
C30 C 0.1884(3) 0.0363(3) 0.0323(3) 0.0491(10) Uani 1 1 d . . .
O10 O -0.0737(4) 0.3597(4) 0.4150(4) 0.133(2) Uani 1 1 d . . .
C14 C 0.1855(4) 0.0361(3) 0.2878(2) 0.0482(10) Uani 1 1 d . . .
C29 C 0.1506(4) -0.0458(3) -0.0037(3) 0.0647(13) Uani 1 1 d . . .
H29A H 0.1575 -0.0898 0.0351 0.097 Uiso 1 1 calc R . .
H29B H 0.1921 -0.0599 -0.0455 0.097 Uiso 1 1 calc R . .
H29C H 0.0778 -0.0404 -0.0238 0.097 Uiso 1 1 calc R . .
N5 N 0.0588(5) -0.0887(3) 0.4324(3) 0.0857(16) Uani 1 1 d . . .
C12 C 0.0392(3) 0.1794(3) 0.1566(3) 0.0500(11) Uani 1 1 d . . .
H12 H 0.0531 0.2137 0.1149 0.060 Uiso 1 1 calc R . .
N6 N -0.1119(4) 0.0101(3) 0.3690(3) 0.0905(16) Uani 1 1 d . . .
C31 C 0.1865(4) 0.1086(3) -0.0105(3) 0.0553(12) Uani 1 1 d . . .
H31 H 0.1620 0.1038 -0.0630 0.066 Uiso 1 1 calc R . .
C27 C 0.4110(3) 0.2417(2) 0.2270(2) 0.0397(9) Uani 1 1 d . . .
C17 C 0.6182(4) 0.1376(3) 0.1226(3) 0.0621(13) Uani 1 1 d . . .
H17 H 0.6880 0.1435 0.1119 0.075 Uiso 1 1 calc R . .
C9 C -0.0019(4) 0.0766(3) 0.2784(3) 0.0569(12) Uani 1 1 d . . .
C15 C 0.4553(4) 0.0624(3) 0.1067(3) 0.0562(12) Uani 1 1 d . . .
H15 H 0.4171 0.0162 0.0854 0.067 Uiso 1 1 calc R . .
O9 O 0.1060(4) 0.3566(4) 0.4315(3) 0.1092(16) Uani 1 1 d . . .
C25 C 0.3005(3) 0.3404(3) 0.3187(2) 0.0487(10) Uani 1 1 d . . .
H25 H 0.2604 0.3746 0.3485 0.058 Uiso 1 1 calc R . .
C21 C 0.7228(4) 0.4030(4) 0.2764(3) 0.0673(14) Uani 1 1 d . . .
H21 H 0.7595 0.4494 0.2986 0.081 Uiso 1 1 calc R . .
C4 C 0.1741(4) -0.0212(3) 0.3489(3) 0.0599(13) Uani 1 1 d . . .
C20 C 0.7745(4) 0.3476(4) 0.2302(3) 0.0700(14) Uani 1 1 d . . .
H20 H 0.8454 0.3570 0.2243 0.084 Uiso 1 1 calc R . .
C33 C 0.2202(5) 0.2615(3) -0.0401(3) 0.0717(15) Uani 1 1 d . . .
H33A H 0.2424 0.3122 -0.0121 0.108 Uiso 1 1 calc R . .
H33B H 0.1511 0.2700 -0.0666 0.108 Uiso 1 1 calc R . .
H33C H 0.2689 0.2489 -0.0777 0.108 Uiso 1 1 calc R . .
C2 C 0.3569(5) -0.0528(3) 0.3453(3) 0.0737(16) Uani 1 1 d . . .
H2 H 0.4174 -0.0820 0.3645 0.088 Uiso 1 1 calc R . .
C1 C 0.3605(4) 0.0042(3) 0.2849(3) 0.0608(12) Uani 1 1 d . . .
H1 H 0.4240 0.0122 0.2634 0.073 Uiso 1 1 calc R . .
O8 O 0.0234(5) 0.3539(5) 0.3101(3) 0.142(2) Uani 1 1 d . . .
C10 C -0.0849(4) 0.1262(3) 0.2402(3) 0.0658(14) Uani 1 1 d . . .
H10 H -0.1523 0.1242 0.2565 0.079 Uiso 1 1 calc R . .
C7 C -0.1200(7) -0.0495(5) 0.4250(4) 0.100(2) Uani 1 1 d . . .
H7 H -0.1850 -0.0581 0.4441 0.120 Uiso 1 1 calc R . .
C16 C 0.5606(4) 0.0710(3) 0.0945(3) 0.0638(13) Uani 1 1 d . . .
H16 H 0.5923 0.0296 0.0661 0.077 Uiso 1 1 calc R . .
C11 C -0.0644(4) 0.1766(3) 0.1796(3) 0.0633(13) Uani 1 1 d . . .
H11 H -0.1178 0.2089 0.1534 0.076 Uiso 1 1 calc R . .
C5 C 0.0710(5) -0.0310(3) 0.3753(3) 0.0660(14) Uani 1 1 d . . .
C6 C -0.0344(8) -0.0979(5) 0.4548(4) 0.099(2) Uani 1 1 d . . .
H6 H -0.0445 -0.1385 0.4925 0.118 Uiso 1 1 calc R . .
C8 C -0.0143(5) 0.0176(3) 0.3439(3) 0.0662(14) Uani 1 1 d . . .
O11 O 0.3697(9) -0.0666(6) 0.6720(7) 0.278(6) Uani 1 1 d . . .
C3 C 0.2642(6) -0.0660(3) 0.3769(3) 0.0759(16) Uani 1 1 d . . .
H3 H 0.2612 -0.1051 0.4172 0.091 Uiso 1 1 calc R . .
O7 O 0.0149(7) 0.2396(4) 0.3838(5) 0.186(3) Uani 1 1 d . . .
O3 O 0.4398(13) 0.1368(7) 0.5386(7) 0.347(9) Uani 1 1 d . . .
O4 O 0.3185(13) 0.1453(7) 0.4389(8) 0.318(9) Uani 1 1 d . . .
O6 O 0.4107(13) 0.2542(5) 0.4910(5) 0.364(10) Uani 1 1 d . . .
O5 O 0.4579(12) 0.1499(10) 0.4146(10) 0.348(9) Uani 1 1 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 O2 1.887(3) . ?
Co1 O1 1.893(3) . ?
Co1 N2 1.933(4) . ?
Co1 N3 1.938(4) . ?
Co1 N1 1.944(3) . ?
Co1 N4 1.945(3) . ?
Cl2 O7 1.337(6) . ?
Cl2 O10 1.382(5) . ?
Cl2 O9 1.409(5) . ?
Cl2 O8 1.434(5) . ?
Cl1 O3 1.213(7) . ?
Cl1 O4 1.248(9) . ?
Cl1 O6 1.321(8) . ?
Cl1 O5 1.481(13) . ?
O2 32 1.283(5) . ?
O1 C30 1.293(5) . ?
N8 C21 1.329(6) . ?
N8 C22 1.347(5) . ?
N2 C12 1.323(5) . ?
N2 C13 1.346(5) . ?
N3 C15 1.328(5) . ?
N3 C28 1.358(5) . ?
N4 C26 1.345(5) . ?
N4 C27 1.346(5) . ?
N1 C1 1.327(5) . ?
N1 C14 1.342(6) . ?
C19 N7 1.353(6) . ?
C19 C22 1.413(6) . ?
C19 C18 1.444(6) . ?
C22 C23 1.453(6) . ?
C13 C9 1.374(6) . ?
C13 C14 1.439(6) . ?
C24 C25 1.373(6) . ?
C24 C23 1.387(5) . ?
N7 C20 1.290(7) . ?
C18 C28 1.393(6) . ?
C18 C17 1.406(6) . ?
C23 C27 1.398(5) . ?
C28 C27 1.435(5) . ?
C26 C25 1.384(6) . ?
32 C31 1.395(6) . ?
32 C33 1.490(6) . ?
C30 C31 1.355(6) . ?
C30 C29 1.493(6) . ?
C14 C4 1.404(6) . ?
N5 C6 1.293(9) . ?
N5 C5 1.359(7) . ?
C12 C11 1.415(7) . ?
N6 C7 1.357(8) . ?
N6 C8 1.361(7) . ?
C17 C16 1.342(7) . ?
C9 C10 1.423(7) . ?
C9 C8 1.481(7) . ?
C15 C16 1.385(7) . ?
C21 C20 1.390(8) . ?
C4 C3 1.392(8) . ?
C4 C5 1.441(8) . ?
C2 C3 1.364(8) . ?
C2 C1 1.379(7) . ?
C10 C11 1.356(7) . ?
C7 C6 1.385(11) . ?
C5 C8 1.393(8) . ?

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 O1 96.53(13) . . ?
O2 Co1 N2 93.98(14) . . ?
O1 Co1 N2 87.77(13) . . ?
O2 Co1 N3 87.38(14) . . ?
O1 Co1 N3 93.95(13) . . ?
N2 Co1 N3 177.68(14) . . ?
O2 Co1 N1 176.30(14) . . ?
O1 Co1 N1 86.50(14) . . ?
N2 Co1 N1 83.99(15) . . ?
N3 Co1 N1 94.54(15) . . ?
O2 Co1 N4 85.31(13) . . ?
O1 Co1 N4 177.04(13) . . ?
N2 Co1 N4 94.43(14) . . ?
N3 Co1 N4 83.79(14) . . ?
N1 Co1 N4 91.75(14) . . ?
O7 Cl2 O10 115.1(5) . . ?
O7 Cl2 O9 112.8(4) . . ?
O10 Cl2 O9 109.4(3) . . ?
O7 Cl2 O8 105.8(5) . . ?
O10 Cl2 O8 108.7(4) . . ?
O9 Cl2 O8 104.2(3) . . ?
O3 Cl1 O4 126.3(9) . . ?
O3 Cl1 O6 107.3(7) . . ?
O4 Cl1 O6 119.3(7) . . ?
O3 Cl1 O5 107.5(11) . . ?
O4 Cl1 O5 85.8(9) . . ?
O6 Cl1 O5 104.9(9) . . ?
32 O2 Co1 124.2(3) . . ?
C30 O1 Co1 123.0(3) . . ?
C21 N8 C22 116.3(4) . . ?
C12 N2 C13 119.4(4) . . ?
C12 N2 Co1 127.8(3) . . ?
C13 N2 Co1 112.8(3) . . ?
C15 N3 C28 118.3(4) . . ?
C15 N3 Co1 129.2(3) . . ?
C28 N3 Co1 112.4(3) . . ?
C26 N4 C27 118.5(3) . . ?
C26 N4 Co1 129.1(3) . . ?
C27 N4 Co1 112.3(3) . . ?
C1 N1 C14 118.3(4) . . ?
C1 N1 Co1 129.3(3) . . ?
C14 N1 Co1 112.3(3) . . ?
N7 C19 C22 120.7(4) . . ?
N7 C19 C18 118.6(4) . . ?
C22 C19 C18 120.7(4) . . ?
N8 C22 C19 120.8(4) . . ?
N8 C22 C23 118.9(4) . . ?
C19 C22 C23 120.3(4) . . ?
N2 C13 C9 122.9(4) . . ?
N2 C13 C14 115.2(4) . . ?
C9 C13 C14 121.9(4) . . ?
C25 C24 C23 119.6(4) . . ?
C20 N7 C19 117.4(4) . . ?
C28 C18 C17 116.4(4) . . ?
C28 C18 C19 118.2(4) . . ?
C17 C18 C19 125.4(4) . . ?
C24 C23 C27 117.3(4) . . ?
C24 C23 C22 124.5(4) . . ?
C27 C23 C22 118.2(4) . . ?
N3 C28 C18 123.5(4) . . ?
N3 C28 C27 115.0(4) . . ?
C18 C28 C27 121.5(4) . . ?
N4 C26 C25 121.4(4) . . ?
O2 32 C31 123.5(4) . . ?
O2 32 C33 115.7(4) . . ?
C31 32 C33 120.8(4) . . ?
O1 C30 C31 125.1(4) . . ?
O1 C30 C29 113.9(4) . . ?
C31 C30 C29 121.0(4) . . ?
N1 C14 C4 123.4(4) . . ?
N1 C14 C13 115.7(4) . . ?
C4 C14 C13 120.9(4) . . ?
C6 N5 C5 117.7(7) . . ?
N2 C12 C11 121.6(5) . . ?
C7 N6 C8 114.9(6) . . ?
C30 C31 32 127.1(4) . . ?
N4 C27 C23 123.1(4) . . ?
N4 C27 C28 115.7(4) . . ?
C23 C27 C28 121.1(4) . . ?
C16 C17 C18 119.3(5) . . ?
C13 C9 C10 117.8(4) . . ?
C13 C9 C8 117.7(5) . . ?
C10 C9 C8 124.5(5) . . ?
N3 C15 C16 120.9(4) . . ?
C24 C25 C26 120.0(4) . . ?
N8 C21 C20 122.3(5) . . ?
C3 C4 C14 116.3(5) . . ?
C3 C4 C5 125.6(5) . . ?
C14 C4 C5 118.0(5) . . ?
N7 C20 C21 122.5(5) . . ?
C3 C2 C1 119.7(5) . . ?
N1 C1 C2 122.2(5) . . ?
C11 C10 C9 119.1(5) . . ?
N6 C7 C6 122.1(7) . . ?
C17 C16 C15 121.6(4) . . ?
C10 C11 C12 119.3(5) . . ?
N5 C5 C8 120.5(6) . . ?
N5 C5 C4 118.2(6) . . ?
C8 C5 C4 121.3(5) . . ?
N5 C6 C7 122.7(7) . . ?
N6 C8 C5 122.0(5) . . ?
N6 C8 C9 117.8(6) . . ?
C5 C8 C9 120.1(5) . . ?
C2 C3 C4 120.0(5) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.957
_refine_diff_density_min         -0.613
_refine_diff_density_rms         0.100
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol/acetone'
