# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 938463'
_audit_update_record             
;
2013-05-09 deposited with the CCDC.
2017-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H26 Cl2 Co N4 O9'
_chemical_formula_weight         644.32

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/c

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

_cell_length_a                   18.258(3)
_cell_length_b                   11.0640(9)
_cell_length_c                   14.3340(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.816(5)
_cell_angle_gamma                90.00
_cell_volume                     2834.3(6)
_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       Needle
_exptl_crystal_colour            'Translucent yellow'
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1324
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   
;
Interpolation using  Int.Tab. Vol. C (1992) p. 523,Tab. 6.3.3.3
for values of muR in the range 0-2.5, and Int.Tab. Vol.II (1959)
p.302; Table 5.3.6 B for muR in the range 2.6-10.0.
The interpolation procedure of C.W.Dwiggins Jr (Acta Cryst.(1975)
A31,146-148) is used with some modification.
;
_exptl_absorpt_correction_T_min  0.7431
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_ave  0.7441
_exptl_absorpt_coefficient_mu    0.851
_exptl_crystal_size_rad          0.2000

_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  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22121
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_sigmaI/netI    0.0995
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.20
_diffrn_reflns_theta_max         28.04
_reflns_number_total             6756
_reflns_number_gt                3806
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SIR92, J. Appl. Cryst. 26, 343-350, (1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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 > 2sigma(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)+(0.0708P)²+2.8932P] 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         6756
_refine_ls_number_parameters     373
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1511
_refine_ls_R_factor_gt           0.0786
_refine_ls_wR_factor_ref         0.2024
_refine_ls_wR_factor_gt          0.1680
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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 -0.74345(3) -0.03474(5) -0.86320(4) 0.0423(2) Uani 1 1 d . . .
Cl2 Cl -0.55875(7) 0.28767(12) -0.85837(9) 0.0617(4) Uani 1 1 d . . .
Cl1 Cl -0.87415(9) 0.36647(16) -0.81833(11) 0.0771(5) Uani 1 1 d . . .
C23 C -0.7278(5) -0.0245(5) -0.6439(4) 0.0815(19) Uani 1 1 d . . .
O1W O -0.7291(3) 0.1433(4) -0.8166(3) 0.0738(11) Uani 1 1 d D . .
N2 N -0.6953(2) 0.0099(3) -0.9788(2) 0.0469(9) Uani 1 1 d . . .
N3 N -0.8537(2) -0.0911(4) -0.9037(3) 0.0568(11) Uani 1 1 d . . .
N1 N -0.6798(2) -0.1896(3) -0.8702(2) 0.0452(9) Uani 1 1 d . . .
C7 C -0.6375(3) -0.0626(5) -0.9855(3) 0.0502(12) Uani 1 1 d . . .
N4 N -0.7742(3) -0.0464(3) -0.7294(3) 0.0577(11) Uani 1 1 d . . .
C20 C -0.8811(6) -0.0320(6) -0.6595(7) 0.115(3) Uani 1 1 d . . .
H20 H -0.9328 -0.0346 -0.6660 0.138 Uiso 1 1 calc R . .
C6 C -0.6278(3) -0.1715(4) -0.9255(3) 0.0491(12) Uani 1 1 d . . .
C8 C -0.5919(3) -0.0352(7) -1.0487(4) 0.0764(19) Uani 1 1 d . . .
H8 H -0.5512 -0.0842 -1.0524 0.092 Uiso 1 1 calc R . .
O7 O -0.5118(3) 0.3508(5) -0.7852(3) 0.1113(17) Uani 1 1 d . . .
O5 O -0.6341(3) 0.3165(4) -0.8565(5) 0.126(2) Uani 1 1 d . . .
C19 C -0.8481(4) -0.0529(5) -0.7367(5) 0.0735(17) Uani 1 1 d . . .
C9 C -0.6073(5) 0.0654(9) -1.1061(4) 0.098(3) Uani 1 1 d . . .
H9 H -0.5772 0.0857 -1.1488 0.117 Uiso 1 1 calc R . .
C3 C -0.6251(4) -0.3807(6) -0.8260(4) 0.087(2) Uani 1 1 d . . .
H3 H -0.6251 -0.4526 -0.7925 0.104 Uiso 1 1 calc R . .
C2 C -0.6785(3) -0.2946(5) -0.8223(3) 0.0612(14) Uani 1 1 d . . .
O4 O -0.8044(3) 0.3986(6) -0.8402(5) 0.153(2) Uani 1 1 d . . .
O6 O -0.5484(3) 0.1624(4) -0.8552(4) 0.1173(18) Uani 1 1 d . . .
O1 O -0.9281(4) 0.3899(8) -0.8961(5) 0.197(4) Uani 1 1 d . . .
O8 O -0.5471(4) 0.3335(6) -0.9460(3) 0.144(2) Uani 1 1 d . . .
C4 C -0.5714(4) -0.3605(7) -0.8795(6) 0.099(3) Uani 1 1 d . . .
H4 H -0.5344 -0.4177 -0.8815 0.119 Uiso 1 1 calc R . .
C21 C -0.8360(9) -0.0077(7) -0.5742(8) 0.133(5) Uani 1 1 d . . .
H21 H -0.8568 0.0072 -0.5213 0.160 Uiso 1 1 calc R . .
C11 C -0.7116(3) 0.1062(5) -1.0356(3) 0.0638(15) Uani 1 1 d . . .
C14 C -0.8874(3) -0.1334(5) -0.9918(5) 0.0802(18) Uani 1 1 d . . .
C13 C -0.8435(4) -0.1417(6) -1.0677(4) 0.095(2) Uani 1 1 d . . .
H13A H -0.7970 -0.1821 -1.0433 0.142 Uiso 1 1 calc R . .
H13B H -0.8337 -0.0619 -1.0883 0.142 Uiso 1 1 calc R . .
H13C H -0.8714 -0.1864 -1.1206 0.142 Uiso 1 1 calc R . .
C24 C -0.6460(5) -0.0199(7) -0.6409(5) 0.117(3) Uani 1 1 d . . .
H24A H -0.6363 0.0348 -0.6890 0.175 Uiso 1 1 calc R . .
H24B H -0.6285 -0.0991 -0.6526 0.175 Uiso 1 1 calc R . .
H24C H -0.6205 0.0076 -0.5793 0.175 Uiso 1 1 calc R . .
C10 C -0.6665(5) 0.1330(7) -1.0992(4) 0.092(2) Uani 1 1 d . . .
H10 H -0.6777 0.2003 -1.1384 0.110 Uiso 1 1 calc R . .
C18 C -0.8920(3) -0.0886(6) -0.8321(5) 0.0772(17) Uani 1 1 d . . .
C5 C -0.5737(3) -0.2555(6) -0.9290(4) 0.0791(18) Uani 1 1 d . . .
H5 H -0.5380 -0.2406 -0.9655 0.095 Uiso 1 1 calc R . .
C12 C -0.7797(4) 0.1803(6) -1.0299(4) 0.091(2) Uani 1 1 d . . .
H12A H -0.8156 0.1305 -1.0076 0.136 Uiso 1 1 calc R . .
H12B H -0.8015 0.2113 -1.0920 0.136 Uiso 1 1 calc R . .
H12C H -0.7656 0.2464 -0.9866 0.136 Uiso 1 1 calc R . .
C16 C -0.9989(5) -0.1673(12) -0.9371(11) 0.175(5) Uani 1 1 d . . .
H16 H -1.0483 -0.1937 -0.9484 0.209 Uiso 1 1 calc R . .
C1 C -0.7375(4) -0.3167(5) -0.7664(5) 0.097(2) Uani 1 1 d . . .
H1A H -0.7848 -0.2887 -0.8019 0.146 Uiso 1 1 calc R . .
H1B H -0.7252 -0.2740 -0.7069 0.146 Uiso 1 1 calc R . .
H1C H -0.7405 -0.4017 -0.7543 0.146 Uiso 1 1 calc R . .
O3 O -0.8830(4) 0.4403(6) -0.7428(4) 0.164(3) Uani 1 1 d . . .
O2 O -0.8725(4) 0.2452(6) -0.7939(6) 0.176(3) Uani 1 1 d . . .
C15 C -0.9599(5) -0.1717(9) -1.0076(8) 0.135(3) Uani 1 1 d . . .
H15 H -0.9827 -0.2011 -1.0673 0.162 Uiso 1 1 calc R . .
C17 C -0.9655(5) -0.1236(10) -0.8481(8) 0.143(4) Uani 1 1 d . . .
H17 H -0.9926 -0.1180 -0.7998 0.172 Uiso 1 1 calc R . .
C22 C -0.7593(8) -0.0048(6) -0.5653(5) 0.121(4) Uani 1 1 d . . .
H22 H -0.7287 0.0104 -0.5062 0.146 Uiso 1 1 calc R . .
H1WB H -0.698(4) 0.199(5) -0.831(5) 0.14(3) Uiso 1 1 d D . .
H1WA H -0.765(3) 0.187(6) -0.800(5) 0.11(3) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 N3 2.074(4) . ?
Co1 O1W 2.079(4) . ?
Co1 N1 2.085(4) . ?
Co1 N2 2.088(4) . ?
Co1 N4 2.110(4) . ?
Cl2 O7 1.398(4) . ?
Cl2 O6 1.399(5) . ?
Cl2 O8 1.410(5) . ?
Cl2 O5 1.417(4) . ?
Cl1 O1 1.352(6) . ?
Cl1 O2 1.385(6) . ?
Cl1 O3 1.391(5) . ?
Cl1 O4 1.417(6) . ?
C23 N4 1.362(7) . ?
C23 C22 1.383(11) . ?
C23 C24 1.485(10) . ?
N2 C11 1.338(6) . ?
N2 C7 1.344(6) . ?
N3 C18 1.355(7) . ?
N3 C14 1.369(7) . ?
N1 C2 1.347(6) . ?
N1 C6 1.370(6) . ?
C7 C8 1.384(7) . ?
C7 C6 1.469(7) . ?
N4 C19 1.334(7) . ?
C20 C21 1.354(13) . ?
C20 C19 1.384(9) . ?
C6 C5 1.365(7) . ?
C8 C9 1.379(10) . ?
C19 C18 1.489(9) . ?
C9 C10 1.334(10) . ?
C3 C2 1.371(8) . ?
C3 C4 1.380(10) . ?
C2 C1 1.490(8) . ?
C4 C5 1.358(10) . ?
C21 C22 1.380(13) . ?
C11 C10 1.379(9) . ?
C11 C12 1.507(8) . ?
C14 C15 1.365(10) . ?
C14 C13 1.479(9) . ?
C18 C17 1.371(9) . ?
C16 C15 1.351(13) . ?
C16 C17 1.383(14) . ?

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
N3 Co1 O1W 115.21(18) . . ?
N3 Co1 N1 104.97(15) . . ?
O1W Co1 N1 139.42(17) . . ?
N3 Co1 N2 113.06(16) . . ?
O1W Co1 N2 89.15(16) . . ?
N1 Co1 N2 80.00(15) . . ?
N3 Co1 N4 79.18(18) . . ?
O1W Co1 N4 78.76(16) . . ?
N1 Co1 N4 104.39(15) . . ?
N2 Co1 N4 165.82(16) . . ?
O7 Cl2 O6 114.4(3) . . ?
O7 Cl2 O8 107.9(4) . . ?
O6 Cl2 O8 110.0(4) . . ?
O7 Cl2 O5 108.7(3) . . ?
O6 Cl2 O5 110.4(3) . . ?
O8 Cl2 O5 105.1(4) . . ?
O1 Cl1 O2 111.6(5) . . ?
O1 Cl1 O3 110.3(5) . . ?
O2 Cl1 O3 111.8(5) . . ?
O1 Cl1 O4 107.8(5) . . ?
O2 Cl1 O4 108.9(4) . . ?
O3 Cl1 O4 106.1(4) . . ?
N4 C23 C22 118.3(8) . . ?
N4 C23 C24 117.9(6) . . ?
C22 C23 C24 123.7(8) . . ?
C11 N2 C7 120.8(4) . . ?
C11 N2 Co1 126.5(4) . . ?
C7 N2 Co1 112.3(3) . . ?
C18 N3 C14 120.1(5) . . ?
C18 N3 Co1 113.8(4) . . ?
C14 N3 Co1 126.0(4) . . ?
C2 N1 C6 118.6(4) . . ?
C2 N1 Co1 129.5(3) . . ?
C6 N1 Co1 111.5(3) . . ?
N2 C7 C8 120.2(5) . . ?
N2 C7 C6 116.7(4) . . ?
C8 C7 C6 123.1(5) . . ?
C19 N4 C23 120.9(5) . . ?
C19 N4 Co1 112.6(4) . . ?
C23 N4 Co1 125.1(4) . . ?
C21 C20 C19 118.2(9) . . ?
C5 C6 N1 120.9(5) . . ?
C5 C6 C7 122.6(5) . . ?
N1 C6 C7 116.4(4) . . ?
C9 C8 C7 119.4(6) . . ?
N4 C19 C20 121.8(8) . . ?
N4 C19 C18 115.6(5) . . ?
C20 C19 C18 122.6(7) . . ?
C10 C9 C8 118.6(6) . . ?
C2 C3 C4 120.0(6) . . ?
N1 C2 C3 121.2(6) . . ?
N1 C2 C1 118.5(5) . . ?
C3 C2 C1 120.3(6) . . ?
C5 C4 C3 118.6(6) . . ?
C20 C21 C22 120.4(9) . . ?
N2 C11 C10 119.1(6) . . ?
N2 C11 C12 118.9(5) . . ?
C10 C11 C12 122.0(6) . . ?
C15 C14 N3 119.7(8) . . ?
C15 C14 C13 120.8(7) . . ?
N3 C14 C13 119.4(5) . . ?
C9 C10 C11 122.0(7) . . ?
N3 C18 C17 120.5(7) . . ?
N3 C18 C19 115.9(5) . . ?
C17 C18 C19 123.5(7) . . ?
C4 C5 C6 120.6(6) . . ?
C15 C16 C17 120.2(8) . . ?
C16 C15 C14 120.5(9) . . ?
C18 C17 C16 118.9(9) . . ?
C21 C22 C23 120.3(9) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        28.04
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.068
####################################################################### 
# 
# 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_uc464
_database_code_depnum_ccdc_archive 'CCDC 952077'
_audit_update_record             
;
2013-07-24 deposited with the CCDC.
2017-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H24 Co N4, 2(Cl O4)'
_chemical_formula_sum            'C24 H24 Cl2 Co N4 O8'
_chemical_formula_weight         626.30

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'
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'
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 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'


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

_cell_length_a                   18.0546(11)
_cell_length_b                   11.9616(7)
_cell_length_c                   13.4228(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.413(3)
_cell_angle_gamma                90.00
_cell_volume                     2794.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3657
_cell_measurement_theta_min      2.3187
_cell_measurement_theta_max      21.5621

_exptl_crystal_description       needles
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1284
_exptl_absorpt_coefficient_mu    0.858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.918
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   '(SADABS;  Sheldrick, 2000)'

_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 APEX2 CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16876
_diffrn_reflns_av_R_equivalents  0.0732
_diffrn_reflns_av_sigmaI/netI    0.0776
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         26.10
_reflns_number_total             5471
_reflns_number_gt                3014
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2003)'
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_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 > 2sigma(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)+(0.1730P)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         5471
_refine_ls_number_parameters     365
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1351
_refine_ls_R_factor_gt           0.0805
_refine_ls_wR_factor_ref         0.2650
_refine_ls_wR_factor_gt          0.2239
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_restrained_S_all      0.972
_refine_ls_shift/su_max          0.098
_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
C1 C 0.1907(4) -0.1820(5) 0.3349(5) 0.0711(16) Uani 1 1 d . . .
C2 C 0.1429(5) -0.0961(6) 0.3470(6) 0.096(3) Uani 1 1 d . . .
H2 H 0.1459 -0.0268 0.3169 0.115 Uiso 1 1 calc R . .
C3 C 0.0914(5) -0.1134(8) 0.4032(7) 0.101(3) Uani 1 1 d . . .
H3 H 0.0584 -0.0561 0.4105 0.122 Uiso 1 1 calc R . .
C4 C 0.0879(4) -0.2134(7) 0.4485(6) 0.092(2) Uani 1 1 d . . .
H4 H 0.0530 -0.2250 0.4875 0.110 Uiso 1 1 calc R . .
C5 C 0.1367(3) -0.2980(5) 0.4362(4) 0.0629(14) Uani 1 1 d . . .
C6 C 0.1389(3) -0.4105(5) 0.4848(4) 0.0661(16) Uani 1 1 d . . .
C7 C 0.0930(4) -0.4404(7) 0.5481(5) 0.085(2) Uani 1 1 d . . .
H7 H 0.0579 -0.3902 0.5625 0.102 Uiso 1 1 calc R . .
C8 C 0.1008(5) -0.5448(9) 0.5888(6) 0.099(3) Uani 1 1 d . . .
H8 H 0.0699 -0.5672 0.6307 0.118 Uiso 1 1 calc R . .
C9 C 0.1526(5) -0.6162(7) 0.5692(6) 0.096(2) Uani 1 1 d . . .
H9 H 0.1589 -0.6863 0.6002 0.115 Uiso 1 1 calc R . .
C10 C 0.1977(4) -0.5863(5) 0.5020(5) 0.0714(17) Uani 1 1 d . . .
C11 C 0.2462(5) -0.1718(6) 0.2675(6) 0.101(2) Uani 1 1 d . . .
H11A H 0.2336 -0.2268 0.2135 0.151 Uiso 1 1 calc R . .
H11B H 0.2977 -0.1838 0.3089 0.151 Uiso 1 1 calc R . .
H11C H 0.2421 -0.0985 0.2375 0.151 Uiso 1 1 calc R . .
C12 C 0.2521(4) -0.6603(5) 0.4719(6) 0.091(2) Uani 1 1 d . . .
H12A H 0.2862 -0.6169 0.4434 0.137 Uiso 1 1 calc R . .
H12B H 0.2246 -0.7124 0.4209 0.137 Uiso 1 1 calc R . .
H12C H 0.2812 -0.7004 0.5314 0.137 Uiso 1 1 calc R . .
C13 C 0.4072(4) -0.3529(7) 0.5012(6) 0.097(2) Uani 1 1 d . . .
C14 C 0.4852(6) -0.3333(10) 0.5132(10) 0.153(4) Uani 1 1 d . . .
H14 H 0.5151 -0.3034 0.5747 0.183 Uiso 1 1 calc R . .
C15 C 0.5171(6) -0.3568(12) 0.4377(12) 0.165(5) Uani 1 1 d . . .
H15 H 0.5691 -0.3433 0.4460 0.198 Uiso 1 1 calc R . .
C16 C 0.4717(5) -0.4025(9) 0.3444(9) 0.136(4) Uani 1 1 d . . .
H16 H 0.4934 -0.4203 0.2908 0.163 Uiso 1 1 calc R . .
C17 C 0.3956(4) -0.4201(6) 0.3345(6) 0.0829(19) Uani 1 1 d . . .
C18 C 0.3420(4) -0.4669(5) 0.2416(5) 0.0705(16) Uani 1 1 d . . .
C19 C 0.3661(5) -0.4990(6) 0.1554(6) 0.093(2) Uani 1 1 d . . .
H19 H 0.4172 -0.4925 0.1542 0.111 Uiso 1 1 calc R . .
C20 C 0.3109(6) -0.5409(7) 0.0717(7) 0.104(3) Uani 1 1 d . . .
H20 H 0.3242 -0.5607 0.0117 0.124 Uiso 1 1 calc R . .
C21 C 0.2364(6) -0.5534(6) 0.0772(6) 0.095(2) Uani 1 1 d . . .
H21 H 0.1997 -0.5828 0.0210 0.114 Uiso 1 1 calc R . .
C22 C 0.2156(4) -0.5229(5) 0.1645(4) 0.0674(16) Uani 1 1 d . . .
C23 C 0.3687(5) -0.3276(7) 0.5857(6) 0.118(3) Uani 1 1 d . . .
H23A H 0.3341 -0.3872 0.5900 0.176 Uiso 1 1 calc R . .
H23B H 0.3405 -0.2588 0.5702 0.176 Uiso 1 1 calc R . .
H23C H 0.4069 -0.3205 0.6505 0.176 Uiso 1 1 calc R . .
C24 C 0.1369(4) -0.5346(6) 0.1742(5) 0.088(2) Uani 1 1 d . . .
H24A H 0.1282 -0.4805 0.2226 0.132 Uiso 1 1 calc R . .
H24B H 0.1300 -0.6085 0.1982 0.132 Uiso 1 1 calc R . .
H24C H 0.1011 -0.5226 0.1080 0.132 Uiso 1 1 calc R . .
Cl1 Cl 0.03955(10) -0.79327(14) 0.33384(12) 0.0756(5) Uani 1 1 d . . .
Cl2 Cl 0.63953(14) -0.3586(2) 0.21065(18) 0.1151(8) Uani 1 1 d . . .
Co1 Co 0.25016(4) -0.41691(6) 0.37408(5) 0.0536(3) Uani 1 1 d . . .
N1 N 0.1870(3) -0.2816(4) 0.3795(3) 0.0568(11) Uani 1 1 d . . .
N2 N 0.1901(2) -0.4835(4) 0.4628(3) 0.0559(11) Uani 1 1 d . . .
N3 N 0.3644(3) -0.3973(4) 0.4145(4) 0.0708(13) Uani 1 1 d . . .
N4 N 0.2691(3) -0.4783(4) 0.2452(3) 0.0591(11) Uani 1 1 d . . .
O1 O 0.0549(4) -0.8382(5) 0.4334(4) 0.131(2) Uani 1 1 d . . .
O2 O 0.0295(5) -0.6757(6) 0.3360(5) 0.163(3) Uani 1 1 d . . .
O3A O -0.0040(5) -0.8661(9) 0.2602(6) 0.111(3) Uani 0.66 1 d P . .
O3B O -0.0455(9) -0.7858(19) 0.3164(13) 0.124(6) Uani 0.34 1 d P . .
O4 O 0.1103(5) -0.8045(7) 0.3081(8) 0.207(4) Uani 1 1 d . . .
O5 O 0.6480(6) -0.4306(8) 0.2941(7) 0.185(4) Uani 1 1 d . . .
O6 O 0.7084(9) -0.3789(13) 0.1865(11) 0.288(7) Uani 1 1 d . . .
O7 O 0.5850(9) -0.3872(13) 0.1325(11) 0.358(11) Uani 1 1 d . . .
O8 O 0.6320(10) -0.2558(8) 0.2397(8) 0.298(8) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.344(7) . ?
C1 C2 1.379(9) . ?
C1 C11 1.523(10) . ?
C2 C3 1.360(12) . ?
C2 H2 0.9300 . ?
C3 C4 1.351(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(8) . ?
C4 H4 0.9300 . ?
C5 N1 1.345(7) . ?
C5 C6 1.491(8) . ?
C6 N2 1.360(7) . ?
C6 C7 1.382(9) . ?
C7 C8 1.355(11) . ?
C7 H7 0.9300 . ?
C8 C9 1.344(12) . ?
C8 H8 0.9300 . ?
C9 C10 1.412(10) . ?
C9 H9 0.9300 . ?
C10 N2 1.331(7) . ?
C10 C12 1.456(9) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 N3 1.326(8) . ?
C13 C14 1.394(13) . ?
C13 C23 1.510(11) . ?
C14 C15 1.321(15) . ?
C14 H14 0.9300 . ?
C15 C16 1.412(15) . ?
C15 H15 0.9300 . ?
C16 C17 1.363(11) . ?
C16 H16 0.9300 . ?
C17 N3 1.365(9) . ?
C17 C18 1.471(10) . ?
C18 N4 1.337(7) . ?
C18 C19 1.393(9) . ?
C19 C20 1.382(10) . ?
C19 H19 0.9300 . ?
C20 C21 1.375(12) . ?
C20 H20 0.9300 . ?
C21 C22 1.371(9) . ?
C21 H21 0.9300 . ?
C22 N4 1.355(7) . ?
C22 C24 1.467(9) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
Cl1 O3A 1.394(8) . ?
Cl1 O1 1.397(5) . ?
Cl1 O4 1.415(7) . ?
Cl1 O2 1.419(6) . ?
Cl1 O3B 1.493(17) . ?
Cl2 O7 1.280(10) . ?
Cl2 O8 1.308(8) . ?
Cl2 O5 1.389(7) . ?
Cl2 O6 1.387(12) . ?
Co1 N2 1.978(4) . ?
Co1 N4 1.991(4) . ?
Co1 N1 1.992(4) . ?
Co1 N3 2.002(5) . ?
O3A O3B 1.53(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
N1 C1 C2 120.1(7) . . ?
N1 C1 C11 117.0(5) . . ?
C2 C1 C11 122.8(7) . . ?
C3 C2 C1 119.6(7) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 120.4(7) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.1(7) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 120.7(6) . . ?
N1 C5 C6 115.8(5) . . ?
C4 C5 C6 123.5(6) . . ?
N2 C6 C7 121.4(6) . . ?
N2 C6 C5 115.1(5) . . ?
C7 C6 C5 123.5(6) . . ?
C8 C7 C6 118.2(7) . . ?
C8 C7 H7 120.9 . . ?
C6 C7 H7 120.9 . . ?
C9 C8 C7 120.6(7) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 121.0(7) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
N2 C10 C9 118.1(7) . . ?
N2 C10 C12 117.3(5) . . ?
C9 C10 C12 124.7(6) . . ?
C1 C11 H11A 109.5 . . ?
C1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 C14 120.3(9) . . ?
N3 C13 C23 117.5(7) . . ?
C14 C13 C23 122.2(8) . . ?
C15 C14 C13 120.6(10) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 119.6(9) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 118.5(9) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
C16 C17 N3 120.7(8) . . ?
C16 C17 C18 124.0(8) . . ?
N3 C17 C18 115.3(5) . . ?
N4 C18 C19 122.0(6) . . ?
N4 C18 C17 116.1(5) . . ?
C19 C18 C17 122.0(7) . . ?
C20 C19 C18 117.3(7) . . ?
C20 C19 H19 121.4 . . ?
C18 C19 H19 121.4 . . ?
C21 C20 C19 120.0(7) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C22 C21 C20 120.7(7) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.7 . . ?
N4 C22 C21 119.3(7) . . ?
N4 C22 C24 117.9(5) . . ?
C21 C22 C24 122.8(6) . . ?
C13 C23 H23A 109.5 . . ?
C13 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C13 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O3A Cl1 O1 111.7(5) . . ?
O3A Cl1 O4 98.3(6) . . ?
O1 Cl1 O4 103.5(5) . . ?
O3A Cl1 O2 125.6(5) . . ?
O1 Cl1 O2 110.8(4) . . ?
O4 Cl1 O2 103.1(5) . . ?
O3A Cl1 O3B 64.1(9) . . ?
O1 Cl1 O3B 96.2(7) . . ?
O4 Cl1 O3B 157.6(8) . . ?
O2 Cl1 O3B 79.2(9) . . ?
O7 Cl2 O8 112.2(9) . . ?
O7 Cl2 O5 113.0(11) . . ?
O8 Cl2 O5 109.9(7) . . ?
O7 Cl2 O6 107.7(10) . . ?
O8 Cl2 O6 113.9(11) . . ?
O5 Cl2 O6 99.6(6) . . ?
N2 Co1 N4 128.51(19) . . ?
N2 Co1 N1 83.93(19) . . ?
N4 Co1 N1 124.30(18) . . ?
N2 Co1 N3 125.0(2) . . ?
N4 Co1 N3 82.9(2) . . ?
N1 Co1 N3 116.96(19) . . ?
C1 N1 C5 120.1(5) . . ?
C1 N1 Co1 127.4(4) . . ?
C5 N1 Co1 112.4(4) . . ?
C10 N2 C6 120.8(5) . . ?
C10 N2 Co1 126.5(4) . . ?
C6 N2 Co1 112.7(4) . . ?
C13 N3 C17 120.2(6) . . ?
C13 N3 Co1 127.1(5) . . ?
C17 N3 Co1 112.0(4) . . ?
C18 N4 C22 120.7(5) . . ?
C18 N4 Co1 113.1(4) . . ?
C22 N4 Co1 126.1(4) . . ?
Cl1 O3A O3B 61.1(7) . . ?
Cl1 O3B O3A 54.8(7) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.776
_refine_diff_density_min         -0.774
_refine_diff_density_rms         0.106
