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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
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data_4
_database_code_depnum_ccdc_archive 'CCDC 1470082'
_audit_update_record             
;
2016-03-22 deposited with the CCDC.
2016-05-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H19 Cl2 N5 Ni O9'
_chemical_formula_weight         639.04

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   16.309(3)
_cell_length_b                   12.871(3)
_cell_length_c                   23.680(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4970.8(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    17034
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.485

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.708
_exptl_crystal_F_000             2608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.340
_exptl_absorpt_coefficient_mu    1.061
_shelx_estimated_absorpt_T_min   0.689
_shelx_estimated_absorpt_T_max   0.714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.668
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Sortav (Blessing, 1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Kappa CCD'
_diffrn_measurement_method       'Profile from ω scans'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            23795
_diffrn_reflns_av_unetI/netI     0.0952
_diffrn_reflns_av_R_equivalents  0.0974
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.957
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5680
_reflns_number_gt                3538
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
;
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
The coordinated perchlorate anion was disordered.  The disorder was
modelled over two sites in an approx. 71:29 ratio.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0583P)²] 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         5680
_refine_ls_number_parameters     392
_refine_ls_number_restraints     114
_refine_ls_R_factor_all          0.1068
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1319
_refine_ls_wR_factor_gt          0.1124
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.55369(3) 0.41380(3) 0.33123(2) 0.01863(14) Uani 1 1 d . . . . .
Cl1 Cl 0.60968(6) 0.64333(7) 0.27361(4) 0.0283(2) Uani 1 1 d . U . . .
Cl2 Cl 0.18389(5) 0.41584(8) 0.52431(4) 0.0295(2) Uani 1 1 d . . . . .
O1 O 0.29508(13) 0.4720(2) 0.38662(10) 0.0245(6) Uani 1 1 d . . . . .
H1 H 0.2896(6) 0.466(3) 0.4197(17) 0.037 Uiso 1 1 calc R U . . .
O2 O 0.63046(14) 0.54626(19) 0.30191(10) 0.0274(6) Uani 1 1 d . . . . .
O3 O 0.5266(4) 0.6682(5) 0.2818(5) 0.056(2) Uani 0.72(2) 1 d D U P A 1
O4 O 0.6246(7) 0.6277(7) 0.2136(3) 0.061(2) Uani 0.72(2) 1 d D U P A 1
O5 O 0.6628(6) 0.7219(11) 0.2922(5) 0.062(3) Uani 0.72(2) 1 d D U P A 1
O3A O 0.5466(12) 0.6893(15) 0.3099(9) 0.048(4) Uani 0.28(2) 1 d D U P A 2
O4A O 0.5840(16) 0.6282(15) 0.2208(8) 0.052(4) Uani 0.28(2) 1 d D U P A 2
O5A O 0.6782(12) 0.711(2) 0.2778(12) 0.045(5) Uani 0.28(2) 1 d D U P A 2
O6 O 0.25089(15) 0.4757(2) 0.50117(10) 0.0371(7) Uani 1 1 d . . . . .
O7 O 0.18484(18) 0.3137(2) 0.50063(11) 0.0465(8) Uani 1 1 d . . . . .
O8 O 0.10921(18) 0.4667(3) 0.51141(17) 0.0816(13) Uani 1 1 d . . . . .
O9 O 0.1943(2) 0.4086(2) 0.58426(11) 0.0473(8) Uani 1 1 d . . . . .
N1 N 0.47777(16) 0.3079(2) 0.37094(11) 0.0183(6) Uani 1 1 d . . . . .
N2 N 0.51589(17) 0.5120(2) 0.39464(11) 0.0196(6) Uani 1 1 d . . . . .
N3 N 0.45377(16) 0.4458(2) 0.28478(11) 0.0184(6) Uani 1 1 d . . . . .
N4 N 0.58705(18) 0.3528(2) 0.25338(12) 0.0226(7) Uani 1 1 d . . . . .
N5 N 0.65889(19) 0.3681(2) 0.37123(13) 0.0272(7) Uani 1 1 d . . . . .
C1 C 0.37705(19) 0.4523(3) 0.37197(14) 0.0193(8) Uani 1 1 d . . . . .
C2 C 0.4009(2) 0.3383(3) 0.38436(13) 0.0195(8) Uani 1 1 d . . . . .
C3 C 0.3466(2) 0.2714(3) 0.41019(14) 0.0230(8) Uani 1 1 d . . . . .
H3 H 0.2922 0.2934 0.4183 0.028 Uiso 1 1 calc R U . . .
C4 C 0.3717(2) 0.1716(3) 0.42425(14) 0.0258(9) Uani 1 1 d . . . . .
H4 H 0.3348 0.1243 0.4417 0.031 Uiso 1 1 calc R U . . .
C5 C 0.4507(2) 0.1425(3) 0.41259(15) 0.0276(9) Uani 1 1 d . . . . .
H5 H 0.4701 0.0757 0.4234 0.033 Uiso 1 1 calc R U . . .
C6 C 0.5017(2) 0.2111(3) 0.38500(14) 0.0249(8) Uani 1 1 d . . . . .
H6 H 0.5557 0.1894 0.3756 0.030 Uiso 1 1 calc R U . . .
C7 C 0.4356(2) 0.5249(3) 0.40423(13) 0.0184(8) Uani 1 1 d . . . . .
C8 C 0.4074(2) 0.5963(3) 0.44309(14) 0.0241(8) Uani 1 1 d . . . . .
H8 H 0.3502 0.6053 0.4490 0.029 Uiso 1 1 calc R U . . .
C9 C 0.4635(2) 0.6548(3) 0.47354(15) 0.0284(9) Uani 1 1 d . . . . .
H9 H 0.4453 0.7047 0.5003 0.034 Uiso 1 1 calc R U . . .
C10 C 0.5459(2) 0.6395(3) 0.46430(15) 0.0284(9) Uani 1 1 d . . . . .
H10 H 0.5855 0.6774 0.4854 0.034 Uiso 1 1 calc R U . . .
C11 C 0.5702(2) 0.5687(3) 0.42412(15) 0.0252(8) Uani 1 1 d . . . . .
H11 H 0.6271 0.5596 0.4170 0.030 Uiso 1 1 calc R U . . .
C12 C 0.38165(19) 0.4717(3) 0.30777(13) 0.0180(7) Uani 1 1 d . . . . .
C13 C 0.3174(2) 0.5051(3) 0.27499(15) 0.0220(8) Uani 1 1 d . . . . .
H13 H 0.2662 0.5226 0.2916 0.026 Uiso 1 1 calc R U . . .
C14 C 0.3289(2) 0.5128(3) 0.21685(14) 0.0253(9) Uani 1 1 d . . . . .
H14 H 0.2869 0.5405 0.1935 0.030 Uiso 1 1 calc R U . . .
C15 C 0.4022(2) 0.4798(3) 0.19352(14) 0.0240(8) Uani 1 1 d . . . . .
H15 H 0.4103 0.4823 0.1538 0.029 Uiso 1 1 calc R U . . .
C16 C 0.4638(2) 0.4428(3) 0.22865(14) 0.0194(8) Uani 1 1 d . . . . .
C17 C 0.5401(2) 0.3901(3) 0.21057(15) 0.0213(8) Uani 1 1 d . . . . .
C18 C 0.5610(2) 0.3737(3) 0.15447(15) 0.0262(9) Uani 1 1 d . . . . .
H18 H 0.5276 0.4005 0.1250 0.031 Uiso 1 1 calc R U . . .
C19 C 0.6310(2) 0.3178(3) 0.14219(16) 0.0305(9) Uani 1 1 d . . . . .
H19 H 0.6469 0.3062 0.1041 0.037 Uiso 1 1 calc R U . . .
C20 C 0.6777(2) 0.2791(3) 0.18598(16) 0.0319(9) Uani 1 1 d . . . . .
H20 H 0.7258 0.2397 0.1784 0.038 Uiso 1 1 calc R U . . .
C21 C 0.6538(2) 0.2982(3) 0.24090(16) 0.0272(9) Uani 1 1 d . . . . .
H21 H 0.6862 0.2714 0.2709 0.033 Uiso 1 1 calc R U . . .
C22 C 0.7205(2) 0.3448(3) 0.38997(15) 0.0245(8) Uani 1 1 d . . . . .
C23 C 0.7999(2) 0.3145(3) 0.41298(18) 0.0358(10) Uani 1 1 d . . . . .
H23A H 0.8273 0.2670 0.3867 0.054 Uiso 1 1 calc R U . . .
H23B H 0.7920 0.2797 0.4494 0.054 Uiso 1 1 calc R U . . .
H23C H 0.8339 0.3765 0.4184 0.054 Uiso 1 1 calc R U . . .


_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
Ni1 N3 2.009(3) . ?
Ni1 N5 2.046(3) . ?
Ni1 N2 2.057(3) . ?
Ni1 N1 2.068(3) . ?
Ni1 N4 2.076(3) . ?
Ni1 O2 2.226(2) . ?
Cl1 O4A 1.334(15) . ?
Cl1 O5 1.402(9) . ?
Cl1 O3 1.406(5) . ?
Cl1 O5A 1.423(19) . ?
Cl1 O4 1.456(6) . ?
Cl1 O2 1.458(2) . ?
Cl1 O3A 1.465(14) . ?
Cl2 O8 1.416(3) . ?
Cl2 O7 1.429(3) . ?
Cl2 O9 1.433(3) . ?
Cl2 O6 1.445(3) . ?
O1 C1 1.404(4) . ?
O1 H1 0.79(4) . ?
N1 C6 1.347(4) . ?
N1 C2 1.352(4) . ?
N2 C7 1.340(4) . ?
N2 C11 1.343(4) . ?
N3 C12 1.338(4) . ?
N3 C16 1.340(4) . ?
N4 C21 1.329(4) . ?
N4 C17 1.358(4) . ?
N5 C22 1.139(4) . ?
C1 C7 1.539(5) . ?
C1 C12 1.542(4) . ?
C1 C2 1.546(5) . ?
C2 C3 1.378(5) . ?
C3 C4 1.389(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.369(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.379(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.379(4) . ?
C8 C9 1.387(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.376(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.376(5) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.373(4) . ?
C13 C14 1.393(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.481(5) . ?
C17 C18 1.387(5) . ?
C18 C19 1.381(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.380(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.380(5) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.458(5) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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 Ni1 N5 173.03(12) . . ?
N3 Ni1 N2 91.77(11) . . ?
N5 Ni1 N2 95.17(11) . . ?
N3 Ni1 N1 84.16(11) . . ?
N5 Ni1 N1 95.85(11) . . ?
N2 Ni1 N1 83.88(11) . . ?
N3 Ni1 N4 78.69(11) . . ?
N5 Ni1 N4 94.73(12) . . ?
N2 Ni1 N4 163.52(11) . . ?
N1 Ni1 N4 108.15(11) . . ?
N3 Ni1 O2 97.39(10) . . ?
N5 Ni1 O2 83.86(10) . . ?
N2 Ni1 O2 85.75(10) . . ?
N1 Ni1 O2 169.56(10) . . ?
N4 Ni1 O2 82.25(10) . . ?
O5 Cl1 O3 112.8(5) . . ?
O4A Cl1 O5A 113.7(12) . . ?
O5 Cl1 O4 107.6(5) . . ?
O3 Cl1 O4 109.1(4) . . ?
O4A Cl1 O2 112.3(9) . . ?
O5 Cl1 O2 109.3(6) . . ?
O3 Cl1 O2 110.8(3) . . ?
O5A Cl1 O2 108.2(13) . . ?
O4 Cl1 O2 107.0(4) . . ?
O4A Cl1 O3A 112.8(9) . . ?
O5A Cl1 O3A 105.2(11) . . ?
O2 Cl1 O3A 103.9(6) . . ?
O8 Cl2 O7 110.5(2) . . ?
O8 Cl2 O9 110.2(2) . . ?
O7 Cl2 O9 109.13(17) . . ?
O8 Cl2 O6 108.77(18) . . ?
O7 Cl2 O6 109.49(17) . . ?
O9 Cl2 O6 108.68(17) . . ?
C1 O1 H1 109.5 . . ?
Cl1 O2 Ni1 131.99(14) . . ?
C6 N1 C2 118.6(3) . . ?
C6 N1 Ni1 123.2(2) . . ?
C2 N1 Ni1 118.2(2) . . ?
C7 N2 C11 119.3(3) . . ?
C7 N2 Ni1 119.5(2) . . ?
C11 N2 Ni1 121.0(2) . . ?
C12 N3 C16 121.2(3) . . ?
C12 N3 Ni1 122.8(2) . . ?
C16 N3 Ni1 116.0(2) . . ?
C21 N4 C17 118.9(3) . . ?
C21 N4 Ni1 127.7(2) . . ?
C17 N4 Ni1 112.4(2) . . ?
C22 N5 Ni1 174.9(3) . . ?
O1 C1 C7 111.0(3) . . ?
O1 C1 C12 105.1(3) . . ?
C7 C1 C12 111.1(3) . . ?
O1 C1 C2 111.3(3) . . ?
C7 C1 C2 109.1(3) . . ?
C12 C1 C2 109.2(3) . . ?
N1 C2 C3 121.3(3) . . ?
N1 C2 C1 117.6(3) . . ?
C3 C2 C1 121.1(3) . . ?
C2 C3 C4 119.6(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 118.8(3) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 119.2(3) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
N1 C6 C5 122.3(3) . . ?
N1 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
N2 C7 C8 121.4(3) . . ?
N2 C7 C1 116.5(3) . . ?
C8 C7 C1 122.0(3) . . ?
C7 C8 C9 119.3(3) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 118.9(3) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C11 119.1(3) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
N2 C11 C10 122.0(3) . . ?
N2 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
N3 C12 C13 121.2(3) . . ?
N3 C12 C1 113.8(3) . . ?
C13 C12 C1 124.8(3) . . ?
C12 C13 C14 118.5(3) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 H13 120.7 . . ?
C15 C14 C13 119.3(3) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 119.4(3) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
N3 C16 C15 119.8(3) . . ?
N3 C16 C17 113.7(3) . . ?
C15 C16 C17 126.3(3) . . ?
N4 C17 C18 121.5(3) . . ?
N4 C17 C16 114.8(3) . . ?
C18 C17 C16 123.5(3) . . ?
C19 C18 C17 118.9(3) . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C20 C19 C18 119.1(3) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C19 C20 C21 119.2(4) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
N4 C21 C20 122.4(4) . . ?
N4 C21 H21 118.8 . . ?
C20 C21 H21 118.8 . . ?
N5 C22 C23 179.0(4) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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
O4A Cl1 O2 Ni1 -68.7(13) . . . . ?
O5 Cl1 O2 Ni1 145.9(5) . . . . ?
O3 Cl1 O2 Ni1 20.9(6) . . . . ?
O5A Cl1 O2 Ni1 165.0(11) . . . . ?
O4 Cl1 O2 Ni1 -97.9(5) . . . . ?
O3A Cl1 O2 Ni1 53.5(12) . . . . ?
C6 N1 C2 C3 -2.1(5) . . . . ?
Ni1 N1 C2 C3 179.1(2) . . . . ?
C6 N1 C2 C1 175.4(3) . . . . ?
Ni1 N1 C2 C1 -3.4(4) . . . . ?
O1 C1 C2 N1 178.4(3) . . . . ?
C7 C1 C2 N1 -58.8(4) . . . . ?
C12 C1 C2 N1 62.9(4) . . . . ?
O1 C1 C2 C3 -4.1(4) . . . . ?
C7 C1 C2 C3 118.7(3) . . . . ?
C12 C1 C2 C3 -119.6(3) . . . . ?
N1 C2 C3 C4 1.8(5) . . . . ?
C1 C2 C3 C4 -175.6(3) . . . . ?
C2 C3 C4 C5 0.7(5) . . . . ?
C3 C4 C5 C6 -2.9(5) . . . . ?
C2 N1 C6 C5 -0.2(5) . . . . ?
Ni1 N1 C6 C5 178.5(3) . . . . ?
C4 C5 C6 N1 2.7(5) . . . . ?
C11 N2 C7 C8 1.0(5) . . . . ?
Ni1 N2 C7 C8 -174.6(2) . . . . ?
C11 N2 C7 C1 -176.0(3) . . . . ?
Ni1 N2 C7 C1 8.5(4) . . . . ?
O1 C1 C7 N2 178.7(3) . . . . ?
C12 C1 C7 N2 -64.8(4) . . . . ?
C2 C1 C7 N2 55.7(4) . . . . ?
O1 C1 C7 C8 1.7(4) . . . . ?
C12 C1 C7 C8 118.3(3) . . . . ?
C2 C1 C7 C8 -121.3(3) . . . . ?
N2 C7 C8 C9 -1.0(5) . . . . ?
C1 C7 C8 C9 175.8(3) . . . . ?
C7 C8 C9 C10 -0.4(5) . . . . ?
C8 C9 C10 C11 1.7(6) . . . . ?
C7 N2 C11 C10 0.4(5) . . . . ?
Ni1 N2 C11 C10 175.9(3) . . . . ?
C9 C10 C11 N2 -1.8(6) . . . . ?
C16 N3 C12 C13 -5.9(5) . . . . ?
Ni1 N3 C12 C13 172.1(2) . . . . ?
C16 N3 C12 C1 169.8(3) . . . . ?
Ni1 N3 C12 C1 -12.3(4) . . . . ?
O1 C1 C12 N3 -173.2(3) . . . . ?
C7 C1 C12 N3 66.7(4) . . . . ?
C2 C1 C12 N3 -53.6(4) . . . . ?
O1 C1 C12 C13 2.3(4) . . . . ?
C7 C1 C12 C13 -117.8(4) . . . . ?
C2 C1 C12 C13 121.8(3) . . . . ?
N3 C12 C13 C14 -0.7(5) . . . . ?
C1 C12 C13 C14 -175.8(3) . . . . ?
C12 C13 C14 C15 4.6(5) . . . . ?
C13 C14 C15 C16 -2.1(5) . . . . ?
C12 N3 C16 C15 8.3(5) . . . . ?
Ni1 N3 C16 C15 -169.7(3) . . . . ?
C12 N3 C16 C17 -166.7(3) . . . . ?
Ni1 N3 C16 C17 15.2(4) . . . . ?
C14 C15 C16 N3 -4.3(5) . . . . ?
C14 C15 C16 C17 170.1(3) . . . . ?
C21 N4 C17 C18 -0.9(5) . . . . ?
Ni1 N4 C17 C18 168.6(3) . . . . ?
C21 N4 C17 C16 175.5(3) . . . . ?
Ni1 N4 C17 C16 -15.0(4) . . . . ?
N3 C16 C17 N4 0.5(4) . . . . ?
C15 C16 C17 N4 -174.2(3) . . . . ?
N3 C16 C17 C18 176.8(3) . . . . ?
C15 C16 C17 C18 2.1(5) . . . . ?
N4 C17 C18 C19 0.2(5) . . . . ?
C16 C17 C18 C19 -175.9(3) . . . . ?
C17 C18 C19 C20 0.7(5) . . . . ?
C18 C19 C20 C21 -0.8(5) . . . . ?
C17 N4 C21 C20 0.8(5) . . . . ?
Ni1 N4 C21 C20 -167.0(3) . . . . ?
C19 C20 C21 N4 0.1(6) . . . . ?

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
O1 H1 O6 0.79 2.03 2.807(3) 164.9 .

_refine_diff_density_max         0.565
_refine_diff_density_min         -0.631
_refine_diff_density_rms         0.108

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1470083'
_audit_update_record             
;
2016-03-22 deposited with the CCDC.
2016-05-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H26 Cl2 Cu N4 O12'
_chemical_formula_weight         684.92

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5840(17)
_cell_length_b                   11.785(2)
_cell_length_c                   14.702(3)
_cell_angle_alpha                96.70(3)
_cell_angle_beta                 96.70(3)
_cell_angle_gamma                109.93(3)
_cell_volume                     1369.0(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    17808
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.485

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_F_000             702
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.520
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    1.064
_shelx_estimated_absorpt_T_min   0.577
_shelx_estimated_absorpt_T_max   0.675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.546
_exptl_absorpt_correction_T_max  0.658
_exptl_absorpt_process_details   'Sortav (Blessing, 1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'profile from ω scans'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            24985
_diffrn_reflns_av_unetI/netI     0.0781
_diffrn_reflns_av_R_equivalents  0.1141
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.989
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6212
_reflns_number_gt                4529
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Hydrogen atoms bonded to the coordinated water ligand were located in the
Fourier difference map, and were refined with the O-H distance restrained to
0.84 A.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0563P)²+0.7026P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6212
_refine_ls_number_parameters     443
_refine_ls_number_restraints     164
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1329
_refine_ls_wR_factor_gt          0.1180
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.35354(5) 0.25216(3) 0.62225(2) 0.02319(13) Uani 1 1 d . . . . .
H1O H 0.370(4) 0.061(3) 0.556(2) 0.047(12) Uiso 1 1 d D . . . .
Cl1 Cl 0.13878(10) -0.16290(7) 0.47887(6) 0.02940(19) Uani 1 1 d . . . . .
Cl2 Cl 0.12415(10) 0.80225(8) 0.90093(6) 0.0356(2) Uani 1 1 d . U . . .
H2O H 0.433(5) 0.074(3) 0.646(2) 0.048(13) Uiso 1 1 d D . . . .
O1 O 0.2856(3) 0.4588(2) 0.88106(15) 0.0281(5) Uani 1 1 d . . . . .
H1 H 0.340(5) 0.529(4) 0.8870(15) 0.042 Uiso 1 1 calc R U . . .
O2 O 0.4234(3) 0.1117(2) 0.60321(17) 0.0299(5) Uani 1 1 d D . . . .
O3 O 0.2334(4) -0.1685(2) 0.5648(2) 0.0538(8) Uani 1 1 d . . . . .
O4 O -0.0169(3) -0.1527(2) 0.49613(17) 0.0391(6) Uani 1 1 d . . . . .
O5 O 0.2358(3) -0.0555(2) 0.44458(17) 0.0388(6) Uani 1 1 d . . . . .
O6 O 0.1064(3) -0.2717(2) 0.4129(2) 0.0490(7) Uani 1 1 d . . . . .
O7 O 0.1520(4) 0.7139(3) 0.9536(2) 0.0658(9) Uani 1 1 d D . . . .
O8 O 0.1946(9) 0.8005(4) 0.8191(4) 0.0775(19) Uani 0.777(7) 1 d D U P A 1
O9 O -0.0486(5) 0.7796(5) 0.8836(4) 0.0754(17) Uani 0.777(7) 1 d D U P A 1
O10 O 0.2018(7) 0.9239(4) 0.9549(3) 0.0646(14) Uani 0.777(7) 1 d D U P A 1
O8A O 0.2724(16) 0.8437(15) 0.8575(12) 0.053(4) Uani 0.223(7) 1 d D U P A 2
O9A O 0.085(2) 0.8866(14) 0.9449(10) 0.062(4) Uani 0.223(7) 1 d D U P A 2
O10A O -0.0072(18) 0.7329(12) 0.8210(11) 0.066(4) Uani 0.223(7) 1 d D U P A 2
O11 O 0.4480(4) 0.0003(3) 0.75035(19) 0.0520(8) Uani 1 1 d . . . . .
H11A H 0.354(6) -0.046(4) 0.7592(8) 0.078 Uiso 1 1 calc R U . . .
N1 N 0.1980(3) 0.1854(2) 0.71559(17) 0.0219(5) Uani 1 1 d . . . . .
N2 N 0.5455(3) 0.3462(2) 0.74156(17) 0.0214(5) Uani 1 1 d . . . . .
N3 N 0.2921(3) 0.3971(2) 0.63421(17) 0.0222(5) Uani 1 1 d . . . . .
N4 N 0.3701(3) 0.2899(2) 0.49241(18) 0.0265(6) Uani 1 1 d . . . . .
C1 C 0.3143(4) 0.3961(3) 0.8011(2) 0.0223(6) Uani 1 1 d . . . . .
C2 C 0.2006(4) 0.2615(3) 0.7926(2) 0.0223(6) Uani 1 1 d . . . . .
C3 C 0.1048(4) 0.2192(3) 0.8597(2) 0.0308(7) Uani 1 1 d . . . . .
H3 H 0.1063 0.2742 0.9127 0.037 Uiso 1 1 calc R U . . .
C4 C 0.0073(4) 0.0964(3) 0.8489(3) 0.0371(8) Uani 1 1 d . . . . .
H4 H -0.0558 0.0655 0.8953 0.045 Uiso 1 1 calc R U . . .
C5 C 0.0028(4) 0.0193(3) 0.7695(2) 0.0326(8) Uani 1 1 d . . . . .
H5 H -0.0651 -0.0651 0.7598 0.039 Uiso 1 1 calc R U . . .
C6 C 0.0987(4) 0.0673(3) 0.7046(2) 0.0275(7) Uani 1 1 d . . . . .
H6 H 0.0943 0.0143 0.6497 0.033 Uiso 1 1 calc R U . . .
C7 C 0.5005(4) 0.4054(3) 0.8121(2) 0.0219(6) Uani 1 1 d . . . . .
C8 C 0.6146(4) 0.4693(3) 0.8915(2) 0.0274(7) Uani 1 1 d . . . . .
H8 H 0.5805 0.5108 0.9403 0.033 Uiso 1 1 calc R U . . .
C9 C 0.7788(4) 0.4726(3) 0.8998(2) 0.0317(8) Uani 1 1 d . . . . .
H9 H 0.8585 0.5162 0.9540 0.038 Uiso 1 1 calc R U . . .
C10 C 0.8243(4) 0.4107(3) 0.8271(2) 0.0306(7) Uani 1 1 d . . . . .
H10 H 0.9357 0.4111 0.8306 0.037 Uiso 1 1 calc R U . . .
C11 C 0.7043(4) 0.3490(3) 0.7502(2) 0.0272(7) Uani 1 1 d . . . . .
H11 H 0.7354 0.3063 0.7008 0.033 Uiso 1 1 calc R U . . .
C12 C 0.2680(3) 0.4476(3) 0.7152(2) 0.0219(6) Uani 1 1 d . . . . .
C13 C 0.2034(4) 0.5411(3) 0.7189(2) 0.0283(7) Uani 1 1 d . . . . .
H13 H 0.1813 0.5745 0.7759 0.034 Uiso 1 1 calc R U . . .
C14 C 0.1722(4) 0.5840(3) 0.6383(3) 0.0331(8) Uani 1 1 d . . . . .
H14 H 0.1276 0.6476 0.6395 0.040 Uiso 1 1 calc R U . . .
C15 C 0.2051(4) 0.5356(3) 0.5550(2) 0.0323(8) Uani 1 1 d . . . . .
H15 H 0.1878 0.5672 0.4997 0.039 Uiso 1 1 calc R U . . .
C16 C 0.2640(4) 0.4398(3) 0.5552(2) 0.0258(7) Uani 1 1 d . . . . .
C17 C 0.3061(4) 0.3770(3) 0.4737(2) 0.0279(7) Uani 1 1 d . . . . .
C18 C 0.2828(4) 0.4019(3) 0.3845(2) 0.0371(8) Uani 1 1 d . . . . .
H18 H 0.2371 0.4625 0.3721 0.045 Uiso 1 1 calc R U . . .
C19 C 0.3275(5) 0.3368(4) 0.3129(2) 0.0449(10) Uani 1 1 d . . . . .
H19 H 0.3120 0.3521 0.2510 0.054 Uiso 1 1 calc R U . . .
C20 C 0.3938(5) 0.2509(3) 0.3333(2) 0.0414(9) Uani 1 1 d . . . . .
H20 H 0.4257 0.2061 0.2856 0.050 Uiso 1 1 calc R U . . .
C21 C 0.4145(4) 0.2292(3) 0.4234(2) 0.0328(8) Uani 1 1 d . . . . .
H21 H 0.4616 0.1696 0.4368 0.039 Uiso 1 1 calc R U . . .
C22 C 0.5423(8) 0.0703(5) 0.8352(4) 0.0894(19) Uani 1 1 d . . . . .
H22A H 0.6610 0.1051 0.8288 0.134 Uiso 1 1 calc R U . . .
H22B H 0.5304 0.0181 0.8831 0.134 Uiso 1 1 calc R U . . .
H22C H 0.5017 0.1366 0.8529 0.134 Uiso 1 1 calc R U . . .
C23 C 0.605(2) 0.7791(18) 0.9590(9) 0.061(4) Uani 0.630(12) 1 d . U P B 1
H23A H 0.6195 0.8652 0.9580 0.091 Uiso 0.630(12) 1 calc R U P B 1
H23B H 0.7107 0.7672 0.9534 0.091 Uiso 0.630(12) 1 calc R U P B 1
H23C H 0.5700 0.7568 1.0177 0.091 Uiso 0.630(12) 1 calc R U P B 1
O12 O 0.4768(6) 0.7029(4) 0.8825(5) 0.0411(18) Uani 0.630(12) 1 d . U P B 1
H12 H 0.4001 0.7317 0.8745 0.062 Uiso 0.630(12) 1 calc R U P B 1
C23A C 0.588(4) 0.780(3) 0.9274(14) 0.047(5) Uani 0.370(12) 1 d . U P B 2
H23D H 0.6351 0.8480 0.9796 0.071 Uiso 0.370(12) 1 calc R U P B 2
H23E H 0.5490 0.8088 0.8726 0.071 Uiso 0.370(12) 1 calc R U P B 2
H23F H 0.6754 0.7470 0.9138 0.071 Uiso 0.370(12) 1 calc R U P B 2
O12A O 0.4565(10) 0.6897(7) 0.9501(8) 0.047(3) Uani 0.370(12) 1 d . U P B 2
H12A H 0.3948 0.7212 0.9755 0.070 Uiso 0.370(12) 1 calc R U P B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.946(2) . ?
Cu1 N3 1.947(2) . ?
Cu1 N4 2.020(3) . ?
Cu1 N1 2.061(3) . ?
Cu1 N2 2.156(3) . ?
Cl1 O4 1.430(2) . ?
Cl1 O6 1.437(3) . ?
Cl1 O5 1.441(2) . ?
Cl1 O3 1.441(3) . ?
Cl2 O9A 1.283(11) . ?
Cl2 O9 1.400(4) . ?
Cl2 O8 1.408(4) . ?
Cl2 O7 1.434(3) . ?
Cl2 O10 1.445(4) . ?
Cl2 O8A 1.451(12) . ?
Cl2 O10A 1.470(11) . ?
O1 C1 1.406(3) . ?
O1 H1 0.78(4) . ?
O2 H1O 0.827(19) . ?
O2 H2O 0.828(19) . ?
O11 C22 1.400(6) . ?
O11 H11A 0.84(5) . ?
N1 C6 1.340(4) . ?
N1 C2 1.353(4) . ?
N2 C11 1.343(4) . ?
N2 C7 1.349(4) . ?
N3 C12 1.338(4) . ?
N3 C16 1.347(4) . ?
N4 C21 1.339(4) . ?
N4 C17 1.359(4) . ?
C1 C12 1.532(4) . ?
C1 C2 1.534(4) . ?
C1 C7 1.552(4) . ?
C2 C3 1.386(4) . ?
C3 C4 1.382(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.378(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.384(4) . ?
C8 C9 1.387(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.391(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.377(5) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.390(4) . ?
C13 C14 1.375(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.390(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.481(5) . ?
C17 C18 1.383(4) . ?
C18 C19 1.396(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.365(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.381(5) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 O12 1.443(15) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O12 H12 0.8400 . ?
C23A O12A 1.37(3) . ?
C23A H23D 0.9800 . ?
C23A H23E 0.9800 . ?
C23A H23F 0.9800 . ?
O12A H12A 0.8400 . ?

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 Cu1 N3 175.91(10) . . ?
O2 Cu1 N4 95.00(11) . . ?
N3 Cu1 N4 81.28(11) . . ?
O2 Cu1 N1 95.36(10) . . ?
N3 Cu1 N1 88.70(10) . . ?
N4 Cu1 N1 146.84(10) . . ?
O2 Cu1 N2 94.48(10) . . ?
N3 Cu1 N2 86.26(10) . . ?
N4 Cu1 N2 123.95(10) . . ?
N1 Cu1 N2 86.46(10) . . ?
O4 Cl1 O6 109.70(16) . . ?
O4 Cl1 O5 109.29(15) . . ?
O6 Cl1 O5 110.80(16) . . ?
O4 Cl1 O3 109.23(17) . . ?
O6 Cl1 O3 109.84(17) . . ?
O5 Cl1 O3 107.95(16) . . ?
O9 Cl2 O8 112.9(4) . . ?
O9A Cl2 O7 116.2(6) . . ?
O9 Cl2 O7 108.7(2) . . ?
O8 Cl2 O7 110.7(3) . . ?
O9 Cl2 O10 106.1(3) . . ?
O8 Cl2 O10 108.0(3) . . ?
O7 Cl2 O10 110.2(2) . . ?
O9A Cl2 O8A 115.9(9) . . ?
O7 Cl2 O8A 104.1(6) . . ?
O9A Cl2 O10A 110.8(9) . . ?
O7 Cl2 O10A 106.4(5) . . ?
O8A Cl2 O10A 102.0(8) . . ?
C1 O1 H1 109.5 . . ?
Cu1 O2 H1O 114(3) . . ?
Cu1 O2 H2O 120(3) . . ?
H1O O2 H2O 108(4) . . ?
C22 O11 H11A 109.5 . . ?
C6 N1 C2 118.5(3) . . ?
C6 N1 Cu1 122.1(2) . . ?
C2 N1 Cu1 119.3(2) . . ?
C11 N2 C7 118.5(3) . . ?
C11 N2 Cu1 124.6(2) . . ?
C7 N2 Cu1 116.84(19) . . ?
C12 N3 C16 121.1(3) . . ?
C12 N3 Cu1 122.3(2) . . ?
C16 N3 Cu1 116.5(2) . . ?
C21 N4 C17 119.1(3) . . ?
C21 N4 Cu1 127.5(2) . . ?
C17 N4 Cu1 112.8(2) . . ?
O1 C1 C12 110.2(2) . . ?
O1 C1 C2 106.3(2) . . ?
C12 C1 C2 110.0(2) . . ?
O1 C1 C7 110.4(2) . . ?
C12 C1 C7 110.7(2) . . ?
C2 C1 C7 109.1(2) . . ?
N1 C2 C3 121.3(3) . . ?
N1 C2 C1 116.4(3) . . ?
C3 C2 C1 122.3(3) . . ?
C4 C3 C2 119.6(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 119.0(3) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C6 C5 C4 118.7(3) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
N1 C6 C5 122.9(3) . . ?
N1 C6 H6 118.6 . . ?
C5 C6 H6 118.6 . . ?
N2 C7 C8 121.4(3) . . ?
N2 C7 C1 117.0(3) . . ?
C8 C7 C1 121.6(3) . . ?
C7 C8 C9 119.8(3) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C10 118.5(3) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?
C11 C10 C9 118.5(3) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
N2 C11 C10 123.1(3) . . ?
N2 C11 H11 118.4 . . ?
C10 C11 H11 118.4 . . ?
N3 C12 C13 120.7(3) . . ?
N3 C12 C1 116.3(2) . . ?
C13 C12 C1 123.1(3) . . ?
C14 C13 C12 118.4(3) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
C13 C14 C15 120.9(3) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C14 117.9(3) . . ?
C16 C15 H15 121.1 . . ?
C14 C15 H15 121.1 . . ?
N3 C16 C15 120.9(3) . . ?
N3 C16 C17 113.5(3) . . ?
C15 C16 C17 125.6(3) . . ?
N4 C17 C18 121.2(3) . . ?
N4 C17 C16 114.6(3) . . ?
C18 C17 C16 124.2(3) . . ?
C17 C18 C19 119.2(3) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C20 C19 C18 118.8(3) . . ?
C20 C19 H19 120.6 . . ?
C18 C19 H19 120.6 . . ?
C19 C20 C21 120.0(4) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
N4 C21 C20 121.8(3) . . ?
N4 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
O11 C22 H22A 109.5 . . ?
O11 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O11 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O12 C23 H23A 109.5 . . ?
O12 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O12 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C23 O12 H12 109.5 . . ?
O12A C23A H23D 109.5 . . ?
O12A C23A H23E 109.5 . . ?
H23D C23A H23E 109.5 . . ?
O12A C23A H23F 109.5 . . ?
H23D C23A H23F 109.5 . . ?
H23E C23A H23F 109.5 . . ?
C23A O12A H12A 109.5 . . ?

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
C6 N1 C2 C3 0.7(4) . . . . ?
Cu1 N1 C2 C3 -176.6(2) . . . . ?
C6 N1 C2 C1 -179.1(2) . . . . ?
Cu1 N1 C2 C1 3.6(3) . . . . ?
O1 C1 C2 N1 174.9(2) . . . . ?
C12 C1 C2 N1 55.6(3) . . . . ?
C7 C1 C2 N1 -66.1(3) . . . . ?
O1 C1 C2 C3 -4.9(4) . . . . ?
C12 C1 C2 C3 -124.2(3) . . . . ?
C7 C1 C2 C3 114.1(3) . . . . ?
N1 C2 C3 C4 1.3(5) . . . . ?
C1 C2 C3 C4 -178.8(3) . . . . ?
C2 C3 C4 C5 -2.3(5) . . . . ?
C3 C4 C5 C6 1.3(5) . . . . ?
C2 N1 C6 C5 -1.8(4) . . . . ?
Cu1 N1 C6 C5 175.4(2) . . . . ?
C4 C5 C6 N1 0.8(5) . . . . ?
C11 N2 C7 C8 0.8(4) . . . . ?
Cu1 N2 C7 C8 -179.6(2) . . . . ?
C11 N2 C7 C1 -177.8(3) . . . . ?
Cu1 N2 C7 C1 1.9(3) . . . . ?
O1 C1 C7 N2 178.0(2) . . . . ?
C12 C1 C7 N2 -59.7(3) . . . . ?
C2 C1 C7 N2 61.6(3) . . . . ?
O1 C1 C7 C8 -0.5(4) . . . . ?
C12 C1 C7 C8 121.7(3) . . . . ?
C2 C1 C7 C8 -117.0(3) . . . . ?
N2 C7 C8 C9 -0.3(5) . . . . ?
C1 C7 C8 C9 178.2(3) . . . . ?
C7 C8 C9 C10 -0.1(5) . . . . ?
C8 C9 C10 C11 0.0(5) . . . . ?
C7 N2 C11 C10 -0.8(4) . . . . ?
Cu1 N2 C11 C10 179.5(2) . . . . ?
C9 C10 C11 N2 0.4(5) . . . . ?
C16 N3 C12 C13 4.0(4) . . . . ?
Cu1 N3 C12 C13 -171.6(2) . . . . ?
C16 N3 C12 C1 -176.4(3) . . . . ?
Cu1 N3 C12 C1 8.0(3) . . . . ?
O1 C1 C12 N3 179.0(2) . . . . ?
C2 C1 C12 N3 -64.1(3) . . . . ?
C7 C1 C12 N3 56.6(3) . . . . ?
O1 C1 C12 C13 -1.4(4) . . . . ?
C2 C1 C12 C13 115.5(3) . . . . ?
C7 C1 C12 C13 -123.8(3) . . . . ?
N3 C12 C13 C14 -2.9(4) . . . . ?
C1 C12 C13 C14 177.5(3) . . . . ?
C12 C13 C14 C15 -0.3(5) . . . . ?
C13 C14 C15 C16 2.5(5) . . . . ?
C12 N3 C16 C15 -1.7(4) . . . . ?
Cu1 N3 C16 C15 174.2(2) . . . . ?
C12 N3 C16 C17 176.9(3) . . . . ?
Cu1 N3 C16 C17 -7.3(3) . . . . ?
C14 C15 C16 N3 -1.5(5) . . . . ?
C14 C15 C16 C17 -179.9(3) . . . . ?
C21 N4 C17 C18 1.4(5) . . . . ?
Cu1 N4 C17 C18 -170.1(2) . . . . ?
C21 N4 C17 C16 -179.0(3) . . . . ?
Cu1 N4 C17 C16 9.5(3) . . . . ?
N3 C16 C17 N4 -1.8(4) . . . . ?
C15 C16 C17 N4 176.6(3) . . . . ?
N3 C16 C17 C18 177.8(3) . . . . ?
C15 C16 C17 C18 -3.7(5) . . . . ?
N4 C17 C18 C19 -0.5(5) . . . . ?
C16 C17 C18 C19 179.9(3) . . . . ?
C17 C18 C19 C20 -0.4(5) . . . . ?
C18 C19 C20 C21 0.4(5) . . . . ?
C17 N4 C21 C20 -1.4(5) . . . . ?
Cu1 N4 C21 C20 168.8(2) . . . . ?
C19 C20 C21 N4 0.5(5) . . . . ?

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
O2 H1O O3 0.827(19) 2.58(4) 3.092(4) 121(3) .
O2 H1O O5 0.827(19) 1.97(2) 2.793(4) 178(4) .
O2 H2O O11 0.828(19) 1.86(2) 2.682(4) 174(4) .
O1 H1 O12 0.78 2.00 2.779(5) 171.8 .
O1 H1 O12A 0.78 1.88 2.621(8) 157.0 .
O11 H11A O8 0.84 2.21 2.980(6) 152.0 1_545
O11 H11A O8A 0.84 2.08 2.738(12) 134.8 1_545
O12 H12 O7 0.84 2.50 3.127(6) 132.0 .
O12 H12 O8 0.84 2.29 3.112(8) 167.4 .
O12A H12A O7 0.84 2.04 2.730(8) 138.7 .

_refine_diff_density_max         0.442
_refine_diff_density_min         -0.761
_refine_diff_density_rms         0.094

####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1470084'
_audit_update_record             
;
2016-03-22 deposited with the CCDC.
2016-05-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H19 Cd Cl2 N5 O9'
_chemical_formula_weight         692.73

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'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   17.018(3)
_cell_length_b                   12.700(3)
_cell_length_c                   23.847(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5153.9(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    19868
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.485

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.786
_exptl_crystal_F_000             2768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.520
_exptl_crystal_size_min          0.500
_exptl_absorpt_coefficient_mu    1.118
_shelx_estimated_absorpt_T_min   0.563
_shelx_estimated_absorpt_T_max   0.605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.533
_exptl_absorpt_correction_T_max  0.572
_exptl_absorpt_process_details   'Sortav (Blessing, 1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            24358
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_av_R_equivalents  0.0756
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.941
_diffrn_reflns_theta_max         27.464
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5874
_reflns_number_gt                4316
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
The coordinated perchlorate anion was disordered.  The disorder was
modeled over two sites in an approx. 7:3 ratio.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0487P)²+2.4787P] 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         5874
_refine_ls_number_parameters     392
_refine_ls_number_restraints     79
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1048
_refine_ls_wR_factor_gt          0.0943
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.036
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.55918(2) 0.58926(2) 0.66896(2) 0.02217(9) Uani 1 1 d . . . . .
Cl1 Cl 0.61593(5) 0.34708(6) 0.73264(4) 0.0309(2) Uani 1 1 d . . . . .
Cl2 Cl 0.19183(5) 0.58516(6) 0.46993(4) 0.02623(19) Uani 1 1 d . . . . .
O1 O 0.29714(12) 0.52646(18) 0.61136(10) 0.0264(5) Uani 1 1 d D . . . .
H1 H 0.2911(6) 0.536(3) 0.5787(8) 0.040 Uiso 1 1 calc DR U . . .
O2 O 0.63747(15) 0.43178(18) 0.69455(11) 0.0350(6) Uani 1 1 d D . . . .
O3 O 0.5351(3) 0.3241(5) 0.7296(4) 0.065(2) Uani 0.765(16) 1 d D U P A 1
O4 O 0.6316(5) 0.3865(5) 0.7891(2) 0.0588(18) Uani 0.765(16) 1 d D U P A 1
O5 O 0.6628(5) 0.2577(6) 0.7233(4) 0.057(2) Uani 0.765(16) 1 d D U P A 1
O3A O 0.5564(12) 0.2951(13) 0.6980(11) 0.057(5) Uani 0.235(16) 1 d D U P A 2
O4A O 0.5924(16) 0.3765(15) 0.7813(7) 0.055(5) Uani 0.235(16) 1 d D U P A 2
O5A O 0.6829(12) 0.2777(17) 0.7316(12) 0.053(6) Uani 0.235(16) 1 d D U P A 2
O6 O 0.24985(16) 0.5198(2) 0.49696(11) 0.0409(7) Uani 1 1 d . . . . .
O7 O 0.19361(16) 0.68861(19) 0.49423(11) 0.0395(7) Uani 1 1 d . . . . .
O8 O 0.11603(16) 0.5389(2) 0.47753(15) 0.0633(10) Uani 1 1 d . . . . .
O9 O 0.2102(2) 0.59107(19) 0.41155(11) 0.0475(8) Uani 1 1 d . . . . .
N1 N 0.47061(16) 0.6969(2) 0.61965(11) 0.0224(6) Uani 1 1 d . . . . .
N2 N 0.50834(15) 0.47764(19) 0.60319(11) 0.0204(6) Uani 1 1 d . . . . .
N3 N 0.44451(15) 0.5586(2) 0.71596(11) 0.0195(6) Uani 1 1 d . . . . .
N4 N 0.57936(18) 0.6300(2) 0.75996(13) 0.0288(7) Uani 1 1 d . . . . .
N5 N 0.67260(19) 0.6483(2) 0.63155(15) 0.0386(8) Uani 1 1 d . . . . .
C1 C 0.37558(17) 0.5476(2) 0.62588(13) 0.0183(6) Uani 1 1 d . . . . .
C2 C 0.39655(18) 0.6630(2) 0.61098(13) 0.0196(7) Uani 1 1 d . . . . .
C3 C 0.3410(2) 0.7282(3) 0.58651(14) 0.0264(8) Uani 1 1 d . . . . .
H3 H 0.2887 0.7040 0.5813 0.032 Uiso 1 1 calc R U . . .
C4 C 0.3620(2) 0.8292(3) 0.56969(15) 0.0305(8) Uani 1 1 d . . . . .
H4 H 0.3242 0.8746 0.5530 0.037 Uiso 1 1 calc R U . . .
C5 C 0.4378(2) 0.8623(3) 0.57743(16) 0.0317(9) Uani 1 1 d . . . . .
H5 H 0.4539 0.9302 0.5653 0.038 Uiso 1 1 calc R U . . .
C6 C 0.4905(2) 0.7950(2) 0.60327(14) 0.0267(8) Uani 1 1 d . . . . .
H6 H 0.5427 0.8187 0.6097 0.032 Uiso 1 1 calc R U . . .
C7 C 0.43092(18) 0.4717(2) 0.59311(13) 0.0183(7) Uani 1 1 d . . . . .
C8 C 0.4011(2) 0.4028(2) 0.55365(14) 0.0250(7) Uani 1 1 d . . . . .
H8 H 0.3460 0.3974 0.5481 0.030 Uiso 1 1 calc R U . . .
C9 C 0.4520(2) 0.3420(3) 0.52248(15) 0.0304(8) Uani 1 1 d . . . . .
H9 H 0.4323 0.2949 0.4949 0.036 Uiso 1 1 calc R U . . .
C10 C 0.5318(2) 0.3503(3) 0.53163(15) 0.0286(8) Uani 1 1 d . . . . .
H10 H 0.5681 0.3106 0.5100 0.034 Uiso 1 1 calc R U . . .
C11 C 0.5575(2) 0.4176(2) 0.57294(15) 0.0262(8) Uani 1 1 d . . . . .
H11 H 0.6123 0.4217 0.5804 0.031 Uiso 1 1 calc R U . . .
C12 C 0.37902(19) 0.5278(2) 0.68957(14) 0.0201(7) Uani 1 1 d . . . . .
C13 C 0.3172(2) 0.4825(3) 0.71895(15) 0.0270(8) Uani 1 1 d . . . . .
H13 H 0.2703 0.4620 0.7004 0.032 Uiso 1 1 calc R U . . .
C14 C 0.3261(2) 0.4680(3) 0.77631(16) 0.0329(9) Uani 1 1 d . . . . .
H14 H 0.2859 0.4340 0.7972 0.040 Uiso 1 1 calc R U . . .
C15 C 0.3926(2) 0.5024(3) 0.80270(14) 0.0313(8) Uani 1 1 d . . . . .
H15 H 0.3983 0.4937 0.8421 0.038 Uiso 1 1 calc R U . . .
C16 C 0.4519(2) 0.5502(2) 0.77175(14) 0.0227(7) Uani 1 1 d . . . . .
C17 C 0.5244(2) 0.5972(2) 0.79614(15) 0.0268(8) Uani 1 1 d . . . . .
C18 C 0.5345(3) 0.6103(3) 0.85344(17) 0.0402(10) Uani 1 1 d . . . . .
H18 H 0.4956 0.5865 0.8790 0.048 Uiso 1 1 calc R U . . .
C19 C 0.6021(3) 0.6586(3) 0.87304(19) 0.0519(13) Uani 1 1 d . . . . .
H19 H 0.6104 0.6670 0.9122 0.062 Uiso 1 1 calc R U . . .
C20 C 0.6566(3) 0.6940(4) 0.8357(2) 0.0565(14) Uani 1 1 d . . . . .
H20 H 0.7025 0.7293 0.8484 0.068 Uiso 1 1 calc R U . . .
C21 C 0.6442(2) 0.6781(3) 0.77932(18) 0.0409(10) Uani 1 1 d . . . . .
H21 H 0.6827 0.7018 0.7533 0.049 Uiso 1 1 calc R U . . .
C22 C 0.7329(2) 0.6669(3) 0.61524(16) 0.0312(9) Uani 1 1 d . . . . .
C23 C 0.8112(2) 0.6899(3) 0.59426(17) 0.0362(9) Uani 1 1 d . . . . .
H23A H 0.8072 0.7271 0.5584 0.054 Uiso 1 1 calc R U . . .
H23B H 0.8401 0.6239 0.5889 0.054 Uiso 1 1 calc R U . . .
H23C H 0.8391 0.7342 0.6214 0.054 Uiso 1 1 calc R U . . .


_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
Cd1 N5 2.254(3) . ?
Cd1 N4 2.257(3) . ?
Cd1 N3 2.284(3) . ?
Cd1 N2 2.284(3) . ?
Cd1 N1 2.350(3) . ?
Cd1 O2 2.479(2) . ?
Cl1 O4A 1.284(15) . ?
Cl1 O5 1.405(6) . ?
Cl1 O3 1.407(5) . ?
Cl1 O5A 1.441(16) . ?
Cl1 O2 1.455(3) . ?
Cl1 O4 1.460(6) . ?
Cl1 O3A 1.465(14) . ?
Cl2 O9 1.429(3) . ?
Cl2 O8 1.429(3) . ?
Cl2 O7 1.436(3) . ?
Cl2 O6 1.442(2) . ?
O1 C1 1.405(4) . ?
O1 H1 0.795(18) . ?
N1 C6 1.348(4) . ?
N1 C2 1.348(4) . ?
N2 C7 1.341(4) . ?
N2 C11 1.342(4) . ?
N3 C12 1.338(4) . ?
N3 C16 1.341(4) . ?
N4 C17 1.340(5) . ?
N4 C21 1.343(5) . ?
N5 C22 1.123(4) . ?
C1 C12 1.541(4) . ?
C1 C2 1.549(4) . ?
C1 C7 1.558(4) . ?
C2 C3 1.386(4) . ?
C3 C4 1.390(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.369(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.382(4) . ?
C8 C9 1.378(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.380(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.375(5) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.389(4) . ?
C13 C14 1.388(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.368(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.488(5) . ?
C17 C18 1.387(5) . ?
C18 C19 1.384(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.363(7) . ?
C19 H19 0.9500 . ?
C20 C21 1.375(6) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.453(5) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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
N5 Cd1 N4 100.02(12) . . ?
N5 Cd1 N3 169.24(11) . . ?
N4 Cd1 N3 72.38(11) . . ?
N5 Cd1 N2 105.00(11) . . ?
N4 Cd1 N2 149.32(10) . . ?
N3 Cd1 N2 84.69(9) . . ?
N5 Cd1 N1 99.07(10) . . ?
N4 Cd1 N1 116.43(10) . . ?
N3 Cd1 N1 78.28(9) . . ?
N2 Cd1 N1 76.98(9) . . ?
N5 Cd1 O2 84.57(10) . . ?
N4 Cd1 O2 82.34(10) . . ?
N3 Cd1 O2 101.57(9) . . ?
N2 Cd1 O2 82.64(9) . . ?
N1 Cd1 O2 159.56(9) . . ?
O5 Cl1 O3 112.2(4) . . ?
O4A Cl1 O5A 116.2(12) . . ?
O4A Cl1 O2 115.3(9) . . ?
O5 Cl1 O2 110.9(4) . . ?
O3 Cl1 O2 111.6(3) . . ?
O5A Cl1 O2 104.0(10) . . ?
O5 Cl1 O4 108.6(4) . . ?
O3 Cl1 O4 107.3(3) . . ?
O2 Cl1 O4 106.0(3) . . ?
O4A Cl1 O3A 115.2(10) . . ?
O5A Cl1 O3A 105.2(11) . . ?
O2 Cl1 O3A 98.9(7) . . ?
O9 Cl2 O8 110.1(2) . . ?
O9 Cl2 O7 109.91(15) . . ?
O8 Cl2 O7 110.12(19) . . ?
O9 Cl2 O6 108.41(18) . . ?
O8 Cl2 O6 108.95(18) . . ?
O7 Cl2 O6 109.36(16) . . ?
C1 O1 H1 109.5 . . ?
Cl1 O2 Cd1 127.94(15) . . ?
C6 N1 C2 119.1(3) . . ?
C6 N1 Cd1 121.4(2) . . ?
C2 N1 Cd1 119.4(2) . . ?
C7 N2 C11 119.0(3) . . ?
C7 N2 Cd1 122.0(2) . . ?
C11 N2 Cd1 119.0(2) . . ?
C12 N3 C16 121.5(3) . . ?
C12 N3 Cd1 122.0(2) . . ?
C16 N3 Cd1 114.8(2) . . ?
C17 N4 C21 119.6(3) . . ?
C17 N4 Cd1 116.2(2) . . ?
C21 N4 Cd1 124.0(3) . . ?
C22 N5 Cd1 171.8(3) . . ?
O1 C1 C12 104.3(2) . . ?
O1 C1 C2 110.1(2) . . ?
C12 C1 C2 111.8(2) . . ?
O1 C1 C7 109.4(2) . . ?
C12 C1 C7 111.8(2) . . ?
C2 C1 C7 109.3(2) . . ?
N1 C2 C3 120.8(3) . . ?
N1 C2 C1 118.9(3) . . ?
C3 C2 C1 120.3(3) . . ?
C2 C3 C4 119.8(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 119.1(3) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 118.8(3) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
N1 C6 C5 122.4(3) . . ?
N1 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
N2 C7 C8 121.2(3) . . ?
N2 C7 C1 118.0(3) . . ?
C8 C7 C1 120.8(3) . . ?
C9 C8 C7 119.4(3) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 119.4(3) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C11 C10 C9 118.3(3) . . ?
C11 C10 H10 120.9 . . ?
C9 C10 H10 120.9 . . ?
N2 C11 C10 122.6(3) . . ?
N2 C11 H11 118.7 . . ?
C10 C11 H11 118.7 . . ?
N3 C12 C13 121.0(3) . . ?
N3 C12 C1 116.6(3) . . ?
C13 C12 C1 122.4(3) . . ?
C14 C13 C12 118.0(3) . . ?
C14 C13 H13 121.0 . . ?
C12 C13 H13 121.0 . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 119.8(3) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
N3 C16 C15 119.6(3) . . ?
N3 C16 C17 115.7(3) . . ?
C15 C16 C17 124.7(3) . . ?
N4 C17 C18 120.6(3) . . ?
N4 C17 C16 116.9(3) . . ?
C18 C17 C16 122.5(4) . . ?
C19 C18 C17 119.3(4) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C20 C19 C18 119.4(4) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C19 C20 C21 119.1(4) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
N4 C21 C20 121.9(4) . . ?
N4 C21 H21 119.0 . . ?
C20 C21 H21 119.0 . . ?
N5 C22 C23 179.4(4) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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
O4A Cl1 O2 Cd1 -51.6(15) . . . . ?
O5 Cl1 O2 Cd1 161.5(5) . . . . ?
O3 Cl1 O2 Cd1 35.7(5) . . . . ?
O5A Cl1 O2 Cd1 -180.0(12) . . . . ?
O4 Cl1 O2 Cd1 -80.8(4) . . . . ?
O3A Cl1 O2 Cd1 71.9(12) . . . . ?
C6 N1 C2 C3 -1.2(5) . . . . ?
Cd1 N1 C2 C3 174.2(2) . . . . ?
C6 N1 C2 C1 175.6(3) . . . . ?
Cd1 N1 C2 C1 -9.1(4) . . . . ?
O1 C1 C2 N1 -177.2(3) . . . . ?
C12 C1 C2 N1 67.3(4) . . . . ?
C7 C1 C2 N1 -57.0(4) . . . . ?
O1 C1 C2 C3 -0.5(4) . . . . ?
C12 C1 C2 C3 -116.0(3) . . . . ?
C7 C1 C2 C3 119.7(3) . . . . ?
N1 C2 C3 C4 1.2(5) . . . . ?
C1 C2 C3 C4 -175.5(3) . . . . ?
C2 C3 C4 C5 0.3(5) . . . . ?
C3 C4 C5 C6 -1.8(5) . . . . ?
C2 N1 C6 C5 -0.4(5) . . . . ?
Cd1 N1 C6 C5 -175.7(3) . . . . ?
C4 C5 C6 N1 1.9(5) . . . . ?
C11 N2 C7 C8 2.1(4) . . . . ?
Cd1 N2 C7 C8 -179.2(2) . . . . ?
C11 N2 C7 C1 -175.9(3) . . . . ?
Cd1 N2 C7 C1 2.8(4) . . . . ?
O1 C1 C7 N2 -177.6(3) . . . . ?
C12 C1 C7 N2 -62.5(3) . . . . ?
C2 C1 C7 N2 61.8(3) . . . . ?
O1 C1 C7 C8 4.4(4) . . . . ?
C12 C1 C7 C8 119.4(3) . . . . ?
C2 C1 C7 C8 -116.2(3) . . . . ?
N2 C7 C8 C9 -2.6(5) . . . . ?
C1 C7 C8 C9 175.4(3) . . . . ?
C7 C8 C9 C10 0.6(5) . . . . ?
C8 C9 C10 C11 1.7(5) . . . . ?
C7 N2 C11 C10 0.4(5) . . . . ?
Cd1 N2 C11 C10 -178.4(3) . . . . ?
C9 C10 C11 N2 -2.3(5) . . . . ?
C16 N3 C12 C13 -2.3(5) . . . . ?
Cd1 N3 C12 C13 162.3(2) . . . . ?
C16 N3 C12 C1 176.4(3) . . . . ?
Cd1 N3 C12 C1 -19.0(4) . . . . ?
O1 C1 C12 N3 -169.6(3) . . . . ?
C2 C1 C12 N3 -50.7(4) . . . . ?
C7 C1 C12 N3 72.3(3) . . . . ?
O1 C1 C12 C13 9.1(4) . . . . ?
C2 C1 C12 C13 128.0(3) . . . . ?
C7 C1 C12 C13 -109.0(3) . . . . ?
N3 C12 C13 C14 -1.4(5) . . . . ?
C1 C12 C13 C14 180.0(3) . . . . ?
C12 C13 C14 C15 3.1(5) . . . . ?
C13 C14 C15 C16 -1.2(5) . . . . ?
C12 N3 C16 C15 4.2(4) . . . . ?
Cd1 N3 C16 C15 -161.5(2) . . . . ?
C12 N3 C16 C17 -174.1(3) . . . . ?
Cd1 N3 C16 C17 20.3(3) . . . . ?
C14 C15 C16 N3 -2.4(5) . . . . ?
C14 C15 C16 C17 175.7(3) . . . . ?
C21 N4 C17 C18 -1.4(5) . . . . ?
Cd1 N4 C17 C18 174.5(2) . . . . ?
C21 N4 C17 C16 176.6(3) . . . . ?
Cd1 N4 C17 C16 -7.6(4) . . . . ?
N3 C16 C17 N4 -8.7(4) . . . . ?
C15 C16 C17 N4 173.1(3) . . . . ?
N3 C16 C17 C18 169.1(3) . . . . ?
C15 C16 C17 C18 -9.0(5) . . . . ?
N4 C17 C18 C19 0.4(5) . . . . ?
C16 C17 C18 C19 -177.4(3) . . . . ?
C17 C18 C19 C20 1.2(6) . . . . ?
C18 C19 C20 C21 -1.9(6) . . . . ?
C17 N4 C21 C20 0.6(5) . . . . ?
Cd1 N4 C21 C20 -174.9(3) . . . . ?
C19 C20 C21 N4 1.0(6) . . . . ?

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
O1 H1 O6 0.80 2.08 2.846(3) 160.8 .

_refine_diff_density_max         0.574
_refine_diff_density_min         -0.825
_refine_diff_density_rms         0.107

####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 1470085'
_audit_update_record             
;
2016-03-22 deposited with the CCDC.
2016-05-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H22 Mn N6 O, (C2 H3 N), 2(Cl O4)'
_chemical_formula_sum            'C30 H25 Cl2 Mn N7 O9'
_chemical_formula_weight         753.41

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.7935(3)
_cell_length_b                   12.3606(3)
_cell_length_c                   20.9431(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.7290(10)
_cell_angle_gamma                90
_cell_volume                     3242.69(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    27915
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_F_000             1540
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.637
_shelx_estimated_absorpt_T_min   0.857
_shelx_estimated_absorpt_T_max   0.894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8580
_exptl_absorpt_correction_T_max  0.8948
_exptl_absorpt_process_details   'Sortav (Blessing, 1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'profile from ω scans'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            24477
_diffrn_reflns_av_unetI/netI     0.0773
_diffrn_reflns_av_R_equivalents  0.0933
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.091
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             7353
_reflns_number_gt                4968
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997
;
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0707P)²+2.0488P] 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         7353
_refine_ls_number_parameters     492
_refine_ls_number_restraints     169
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1585
_refine_ls_wR_factor_gt          0.1396
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.27847(4) 0.32085(4) 0.47397(2) 0.03129(15) Uani 1 1 d . . . . .
Cl1 Cl 0.40055(7) 0.33537(7) 0.82316(4) 0.0456(2) Uani 1 1 d . . . . .
Cl2 Cl 0.36089(7) 0.19766(6) 0.21183(4) 0.0388(2) Uani 1 1 d . . . . .
O1 O 0.25042(19) 0.49184(18) 0.67137(11) 0.0396(5) Uani 1 1 d . . . . .
H1 H 0.291(3) 0.459(3) 0.7044(16) 0.059 Uiso 1 1 calc R U . . .
O2 O 0.3922(3) 0.4290(3) 0.78447(15) 0.0602(11) Uani 0.817(5) 1 d D U P A 1
O3 O 0.2916(3) 0.2996(4) 0.8215(3) 0.117(2) Uani 0.817(5) 1 d D U P A 1
O4 O 0.4456(4) 0.3574(3) 0.88927(15) 0.0615(11) Uani 0.817(5) 1 d D U P A 1
O5 O 0.4526(5) 0.2496(4) 0.8020(3) 0.1090(19) Uani 0.817(5) 1 d D U P A 1
O5A O 0.4698(14) 0.4439(13) 0.8103(9) 0.070(5) Uiso 0.183(5) 1 d D U P A 2
O4A O 0.4884(15) 0.2630(17) 0.8319(10) 0.075(5) Uiso 0.183(5) 1 d D U P A 2
O3A O 0.3702(14) 0.3557(13) 0.8782(8) 0.055(4) Uiso 0.183(5) 1 d D U P A 2
O2A O 0.3347(14) 0.3250(14) 0.7660(9) 0.082(5) Uiso 0.183(5) 1 d D U P A 2
O6 O 0.2934(2) 0.1472(2) 0.25015(13) 0.0558(7) Uani 1 1 d . . . . .
O7 O 0.3009(2) 0.2184(2) 0.14755(12) 0.0500(6) Uani 1 1 d . . . . .
O8 O 0.4001(2) 0.2987(2) 0.24128(13) 0.0571(7) Uani 1 1 d . . . . .
O9 O 0.4479(2) 0.1267(2) 0.20825(13) 0.0590(7) Uani 1 1 d . . . . .
N1 N 0.19077(19) 0.4739(2) 0.49585(12) 0.0315(6) Uani 1 1 d . . . . .
N2 N 0.40292(19) 0.38553(19) 0.55614(12) 0.0305(6) Uani 1 1 d . . . . .
N3 N 0.4397(2) 0.2919(2) 0.44832(13) 0.0341(6) Uani 1 1 d . . . . .
N4 N 0.21318(19) 0.2629(2) 0.55935(12) 0.0320(6) Uani 1 1 d . . . . .
N5 N 0.2118(2) 0.1530(2) 0.44916(13) 0.0386(6) Uani 1 1 d . . . . .
N6 N 0.2194(2) 0.3560(2) 0.36732(15) 0.0432(7) Uani 1 1 d . . . . .
C1 C 0.2600(3) 0.4394(2) 0.61311(15) 0.0335(7) Uani 1 1 d . . . . .
C2 C 0.1911(2) 0.5049(2) 0.55780(15) 0.0327(7) Uani 1 1 d . . . . .
C3 C 0.1310(2) 0.5910(2) 0.57252(17) 0.0367(7) Uani 1 1 d . . . . .
H3 H 0.1326 0.6105 0.6166 0.044 Uiso 1 1 calc R U . . .
C4 C 0.0685(3) 0.6481(3) 0.52201(18) 0.0399(8) Uani 1 1 d . . . . .
H4 H 0.0259 0.7070 0.5310 0.048 Uiso 1 1 calc R U . . .
C5 C 0.0687(3) 0.6191(3) 0.45915(17) 0.0396(8) Uani 1 1 d . . . . .
H5 H 0.0277 0.6582 0.4237 0.048 Uiso 1 1 calc R U . . .
C6 C 0.1298(2) 0.5314(3) 0.44831(16) 0.0356(7) Uani 1 1 d . . . . .
H6 H 0.1284 0.5107 0.4045 0.043 Uiso 1 1 calc R U . . .
C7 C 0.3782(2) 0.4383(2) 0.60742(15) 0.0331(7) Uani 1 1 d . . . . .
C8 C 0.4553(3) 0.4882(3) 0.65380(16) 0.0394(8) Uani 1 1 d . . . . .
H8 H 0.4358 0.5284 0.6882 0.047 Uiso 1 1 calc R U . . .
C9 C 0.5606(3) 0.4786(3) 0.64949(17) 0.0460(9) Uani 1 1 d . . . . .
H9 H 0.6148 0.5111 0.6815 0.055 Uiso 1 1 calc R U . . .
C10 C 0.5872(3) 0.4218(3) 0.59852(16) 0.0417(8) Uani 1 1 d . . . . .
H10 H 0.6598 0.4137 0.5953 0.050 Uiso 1 1 calc R U . . .
C11 C 0.5065(2) 0.3767(2) 0.55202(15) 0.0328(7) Uani 1 1 d . . . . .
C12 C 0.5266(2) 0.3176(2) 0.49397(16) 0.0330(7) Uani 1 1 d . . . . .
C13 C 0.6290(3) 0.2915(3) 0.48667(18) 0.0413(8) Uani 1 1 d . . . . .
H13 H 0.6889 0.3079 0.5202 0.050 Uiso 1 1 calc R U . . .
C14 C 0.6429(3) 0.2410(3) 0.42961(19) 0.0458(9) Uani 1 1 d . . . . .
H14 H 0.7124 0.2230 0.4235 0.055 Uiso 1 1 calc R U . . .
C15 C 0.5553(3) 0.2179(3) 0.38250(18) 0.0443(8) Uani 1 1 d . . . . .
H15 H 0.5627 0.1846 0.3428 0.053 Uiso 1 1 calc R U . . .
C16 C 0.4553(3) 0.2440(3) 0.39378(17) 0.0409(8) Uani 1 1 d . . . . .
H16 H 0.3946 0.2269 0.3610 0.049 Uiso 1 1 calc R U . . .
C17 C 0.2129(2) 0.3240(2) 0.61220(15) 0.0328(7) Uani 1 1 d . . . . .
C18 C 0.1688(3) 0.2878(3) 0.66366(17) 0.0451(8) Uani 1 1 d . . . . .
H18 H 0.1693 0.3324 0.7007 0.054 Uiso 1 1 calc R U . . .
C19 C 0.1242(3) 0.1854(3) 0.6599(2) 0.0552(10) Uani 1 1 d . . . . .
H19 H 0.0926 0.1591 0.6941 0.066 Uiso 1 1 calc R U . . .
C20 C 0.1259(3) 0.1220(3) 0.60604(18) 0.0482(9) Uani 1 1 d . . . . .
H20 H 0.0959 0.0514 0.6031 0.058 Uiso 1 1 calc R U . . .
C21 C 0.1716(3) 0.1619(2) 0.55627(16) 0.0348(7) Uani 1 1 d . . . . .
C22 C 0.1777(2) 0.0992(3) 0.49740(16) 0.0359(7) Uani 1 1 d . . . . .
C23 C 0.1490(3) -0.0090(3) 0.49076(18) 0.0445(8) Uani 1 1 d . . . . .
H23 H 0.1261 -0.0461 0.5252 0.053 Uiso 1 1 calc R U . . .
C24 C 0.1541(3) -0.0627(3) 0.4333(2) 0.0516(9) Uani 1 1 d . . . . .
H24 H 0.1366 -0.1373 0.4286 0.062 Uiso 1 1 calc R U . . .
C25 C 0.1843(3) -0.0072(3) 0.38376(19) 0.0538(10) Uani 1 1 d . . . . .
H25 H 0.1861 -0.0417 0.3435 0.065 Uiso 1 1 calc R U . . .
C26 C 0.2124(3) 0.1004(3) 0.39354(19) 0.0507(9) Uani 1 1 d . . . . .
H26 H 0.2333 0.1390 0.3589 0.061 Uiso 1 1 calc R U . . .
C27 C 0.1828(3) 0.3617(3) 0.31342(18) 0.0434(8) Uani 1 1 d . . . . .
C28 C 0.1340(4) 0.3698(4) 0.24452(18) 0.0624(11) Uani 1 1 d . . . . .
H28A H 0.1073 0.4435 0.2347 0.094 Uiso 1 1 calc R U . . .
H28B H 0.0746 0.3185 0.2341 0.094 Uiso 1 1 calc R U . . .
H28C H 0.1872 0.3529 0.2183 0.094 Uiso 1 1 calc R U . . .
N7 N 0.0623(10) 0.6240(10) 0.8883(5) 0.080(2) Uani 0.596(5) 1 d D U P B -1
C29 C 0.1012(5) 0.5907(6) 0.8480(3) 0.0571(17) Uani 0.596(5) 1 d D U P B -1
C30 C 0.1361(5) 0.5437(5) 0.7932(3) 0.0526(17) Uani 0.596(5) 1 d D U P B -1
H30A H 0.1567 0.6013 0.7661 0.079 Uiso 0.596(5) 1 calc R U P B -1
H30B H 0.0778 0.5012 0.7673 0.079 Uiso 0.596(5) 1 calc R U P B -1
H30C H 0.1975 0.4965 0.8088 0.079 Uiso 0.596(5) 1 calc R U P B -1
N8 N 0.0763(15) 0.6138(14) 0.9085(8) 0.075(3) Uani 0.404(5) 1 d D U P B -2
C31 C 0.0243(9) 0.5686(9) 0.9385(5) 0.069(3) Uani 0.404(5) 1 d D U P B -2
C32 C 0.000(3) 0.502(3) 0.9912(11) 0.070(4) Uani 0.404(5) 1 d D U P B -2
H32A H -0.0623 0.5321 1.0058 0.105 Uiso 0.404(5) 1 calc R U P B -2
H32B H 0.0612 0.5012 1.0277 0.105 Uiso 0.404(5) 1 calc R U P B -2
H32C H -0.0163 0.4280 0.9754 0.105 Uiso 0.404(5) 1 calc R U P B -2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 N4 2.239(3) . ?
Mn1 N2 2.241(2) . ?
Mn1 N6 2.250(3) . ?
Mn1 N3 2.262(3) . ?
Mn1 N5 2.263(3) . ?
Mn1 N1 2.293(2) . ?
Cl1 O3A 1.312(15) . ?
Cl1 O2A 1.322(17) . ?
Cl1 O5 1.373(4) . ?
Cl1 O2 1.404(3) . ?
Cl1 O4 1.414(3) . ?
Cl1 O4A 1.419(19) . ?
Cl1 O3 1.455(4) . ?
Cl1 O5A 1.660(16) . ?
Cl2 O7 1.431(2) . ?
Cl2 O9 1.431(3) . ?
Cl2 O6 1.436(2) . ?
Cl2 O8 1.437(3) . ?
O1 C1 1.409(4) . ?
O1 H1 0.87(4) . ?
N1 C6 1.337(4) . ?
N1 C2 1.352(4) . ?
N2 C7 1.348(4) . ?
N2 C11 1.349(4) . ?
N3 C16 1.338(4) . ?
N3 C12 1.349(4) . ?
N4 C17 1.340(4) . ?
N4 C21 1.354(4) . ?
N5 C26 1.335(4) . ?
N5 C22 1.353(4) . ?
N6 C27 1.133(4) . ?
C1 C2 1.536(4) . ?
C1 C7 1.541(4) . ?
C1 C17 1.547(4) . ?
C2 C3 1.384(4) . ?
C3 C4 1.383(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.365(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.381(4) . ?
C8 C9 1.374(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.377(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.384(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.485(4) . ?
C12 C13 1.388(4) . ?
C13 C14 1.391(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.364(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.388(4) . ?
C18 C19 1.384(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.376(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.386(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.472(4) . ?
C22 C23 1.387(4) . ?
C23 C24 1.386(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.365(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.382(5) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.455(5) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
N7 C29 1.141(11) . ?
C29 C30 1.435(8) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
N8 C31 1.148(12) . ?
C31 C32 1.462(10) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?

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
N4 Mn1 N2 79.80(9) . . ?
N4 Mn1 N6 138.58(10) . . ?
N2 Mn1 N6 137.41(10) . . ?
N4 Mn1 N3 130.16(9) . . ?
N2 Mn1 N3 72.49(9) . . ?
N6 Mn1 N3 86.18(10) . . ?
N4 Mn1 N5 72.89(9) . . ?
N2 Mn1 N5 132.78(10) . . ?
N6 Mn1 N5 85.08(10) . . ?
N3 Mn1 N5 96.89(10) . . ?
N4 Mn1 N1 80.04(9) . . ?
N2 Mn1 N1 81.51(9) . . ?
N6 Mn1 N1 87.69(10) . . ?
N3 Mn1 N1 133.20(9) . . ?
N5 Mn1 N1 128.70(9) . . ?
O3A Cl1 O2A 124.4(11) . . ?
O5 Cl1 O2 115.8(3) . . ?
O5 Cl1 O4 109.7(3) . . ?
O2 Cl1 O4 112.0(2) . . ?
O3A Cl1 O4A 112.1(11) . . ?
O2A Cl1 O4A 113.4(11) . . ?
O5 Cl1 O3 106.4(4) . . ?
O2 Cl1 O3 106.0(2) . . ?
O4 Cl1 O3 106.2(3) . . ?
O3A Cl1 O5A 104.5(9) . . ?
O2A Cl1 O5A 101.2(10) . . ?
O4A Cl1 O5A 95.5(10) . . ?
O7 Cl2 O9 109.55(16) . . ?
O7 Cl2 O6 109.58(16) . . ?
O9 Cl2 O6 109.05(16) . . ?
O7 Cl2 O8 108.78(15) . . ?
O9 Cl2 O8 110.30(17) . . ?
O6 Cl2 O8 109.57(16) . . ?
C1 O1 H1 109.5 . . ?
C6 N1 C2 116.8(3) . . ?
C6 N1 Mn1 121.6(2) . . ?
C2 N1 Mn1 121.3(2) . . ?
C7 N2 C11 118.8(3) . . ?
C7 N2 Mn1 122.6(2) . . ?
C11 N2 Mn1 118.4(2) . . ?
C16 N3 C12 117.7(3) . . ?
C16 N3 Mn1 125.1(2) . . ?
C12 N3 Mn1 117.0(2) . . ?
C17 N4 C21 119.4(3) . . ?
C17 N4 Mn1 122.9(2) . . ?
C21 N4 Mn1 117.6(2) . . ?
C26 N5 C22 118.2(3) . . ?
C26 N5 Mn1 125.2(2) . . ?
C22 N5 Mn1 116.3(2) . . ?
C27 N6 Mn1 171.3(3) . . ?
O1 C1 C2 105.8(2) . . ?
O1 C1 C7 109.3(3) . . ?
C2 C1 C7 111.6(2) . . ?
O1 C1 C17 109.4(2) . . ?
C2 C1 C17 108.3(2) . . ?
C7 C1 C17 112.2(2) . . ?
N1 C2 C3 122.5(3) . . ?
N1 C2 C1 117.6(3) . . ?
C3 C2 C1 119.8(3) . . ?
C4 C3 C2 118.9(3) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C5 C4 C3 119.3(3) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 118.5(3) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
N1 C6 C5 123.9(3) . . ?
N1 C6 H6 118.0 . . ?
C5 C6 H6 118.0 . . ?
N2 C7 C8 121.8(3) . . ?
N2 C7 C1 117.3(3) . . ?
C8 C7 C1 120.9(3) . . ?
C9 C8 C7 119.0(3) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C10 119.7(3) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C10 C11 119.0(3) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
N2 C11 C10 121.6(3) . . ?
N2 C11 C12 115.3(3) . . ?
C10 C11 C12 123.1(3) . . ?
N3 C12 C13 121.9(3) . . ?
N3 C12 C11 116.2(3) . . ?
C13 C12 C11 121.9(3) . . ?
C12 C13 C14 119.2(3) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C15 C14 C13 119.0(3) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C14 C15 C16 118.6(3) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
N3 C16 C15 123.5(3) . . ?
N3 C16 H16 118.2 . . ?
C15 C16 H16 118.2 . . ?
N4 C17 C18 122.0(3) . . ?
N4 C17 C1 117.6(3) . . ?
C18 C17 C1 120.4(3) . . ?
C19 C18 C17 118.5(3) . . ?
C19 C18 H18 120.7 . . ?
C17 C18 H18 120.7 . . ?
C20 C19 C18 119.6(3) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C21 119.5(3) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
N4 C21 C20 121.0(3) . . ?
N4 C21 C22 116.0(3) . . ?
C20 C21 C22 123.1(3) . . ?
N5 C22 C23 121.2(3) . . ?
N5 C22 C21 116.5(3) . . ?
C23 C22 C21 122.3(3) . . ?
C24 C23 C22 119.3(3) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C25 C24 C23 119.4(3) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C26 118.4(3) . . ?
C24 C25 H25 120.8 . . ?
C26 C25 H25 120.8 . . ?
N5 C26 C25 123.3(3) . . ?
N5 C26 H26 118.3 . . ?
C25 C26 H26 118.3 . . ?
N6 C27 C28 178.9(4) . . ?
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 . . ?
N7 C29 C30 172.3(9) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N8 C31 C32 157.6(18) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

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
C6 N1 C2 C3 0.7(4) . . . . ?
Mn1 N1 C2 C3 -173.9(2) . . . . ?
C6 N1 C2 C1 179.5(3) . . . . ?
Mn1 N1 C2 C1 5.0(3) . . . . ?
O1 C1 C2 N1 176.9(2) . . . . ?
C7 C1 C2 N1 58.1(3) . . . . ?
C17 C1 C2 N1 -65.8(3) . . . . ?
O1 C1 C2 C3 -4.2(4) . . . . ?
C7 C1 C2 C3 -123.0(3) . . . . ?
C17 C1 C2 C3 113.1(3) . . . . ?
N1 C2 C3 C4 -0.4(4) . . . . ?
C1 C2 C3 C4 -179.2(3) . . . . ?
C2 C3 C4 C5 -0.7(5) . . . . ?
C3 C4 C5 C6 1.5(5) . . . . ?
C2 N1 C6 C5 0.1(4) . . . . ?
Mn1 N1 C6 C5 174.7(2) . . . . ?
C4 C5 C6 N1 -1.2(5) . . . . ?
C11 N2 C7 C8 3.4(4) . . . . ?
Mn1 N2 C7 C8 -172.6(2) . . . . ?
C11 N2 C7 C1 -175.6(3) . . . . ?
Mn1 N2 C7 C1 8.5(4) . . . . ?
O1 C1 C7 N2 176.3(2) . . . . ?
C2 C1 C7 N2 -67.0(3) . . . . ?
C17 C1 C7 N2 54.7(4) . . . . ?
O1 C1 C7 C8 -2.7(4) . . . . ?
C2 C1 C7 C8 114.0(3) . . . . ?
C17 C1 C7 C8 -124.2(3) . . . . ?
N2 C7 C8 C9 -3.6(5) . . . . ?
C1 C7 C8 C9 175.3(3) . . . . ?
C7 C8 C9 C10 1.3(5) . . . . ?
C8 C9 C10 C11 1.0(5) . . . . ?
C7 N2 C11 C10 -0.9(4) . . . . ?
Mn1 N2 C11 C10 175.2(2) . . . . ?
C7 N2 C11 C12 -179.9(3) . . . . ?
Mn1 N2 C11 C12 -3.7(3) . . . . ?
C9 C10 C11 N2 -1.2(5) . . . . ?
C9 C10 C11 C12 177.6(3) . . . . ?
C16 N3 C12 C13 -2.8(4) . . . . ?
Mn1 N3 C12 C13 172.2(2) . . . . ?
C16 N3 C12 C11 176.4(3) . . . . ?
Mn1 N3 C12 C11 -8.6(3) . . . . ?
N2 C11 C12 N3 8.2(4) . . . . ?
C10 C11 C12 N3 -170.8(3) . . . . ?
N2 C11 C12 C13 -172.7(3) . . . . ?
C10 C11 C12 C13 8.4(5) . . . . ?
N3 C12 C13 C14 2.5(5) . . . . ?
C11 C12 C13 C14 -176.7(3) . . . . ?
C12 C13 C14 C15 -0.4(5) . . . . ?
C13 C14 C15 C16 -1.1(5) . . . . ?
C12 N3 C16 C15 1.2(5) . . . . ?
Mn1 N3 C16 C15 -173.4(3) . . . . ?
C14 C15 C16 N3 0.7(5) . . . . ?
C21 N4 C17 C18 -1.6(5) . . . . ?
Mn1 N4 C17 C18 177.8(2) . . . . ?
C21 N4 C17 C1 -179.2(3) . . . . ?
Mn1 N4 C17 C1 0.1(4) . . . . ?
O1 C1 C17 N4 178.5(3) . . . . ?
C2 C1 C17 N4 63.6(3) . . . . ?
C7 C1 C17 N4 -60.0(4) . . . . ?
O1 C1 C17 C18 0.8(4) . . . . ?
C2 C1 C17 C18 -114.1(3) . . . . ?
C7 C1 C17 C18 122.3(3) . . . . ?
N4 C17 C18 C19 0.1(5) . . . . ?
C1 C17 C18 C19 177.8(3) . . . . ?
C17 C18 C19 C20 0.8(6) . . . . ?
C18 C19 C20 C21 -0.4(6) . . . . ?
C17 N4 C21 C20 2.0(5) . . . . ?
Mn1 N4 C21 C20 -177.4(3) . . . . ?
C17 N4 C21 C22 -178.4(3) . . . . ?
Mn1 N4 C21 C22 2.2(4) . . . . ?
C19 C20 C21 N4 -1.0(6) . . . . ?
C19 C20 C21 C22 179.4(3) . . . . ?
C26 N5 C22 C23 3.0(5) . . . . ?
Mn1 N5 C22 C23 -171.1(3) . . . . ?
C26 N5 C22 C21 -176.2(3) . . . . ?
Mn1 N5 C22 C21 9.7(4) . . . . ?
N4 C21 C22 N5 -7.9(4) . . . . ?
C20 C21 C22 N5 171.7(3) . . . . ?
N4 C21 C22 C23 172.9(3) . . . . ?
C20 C21 C22 C23 -7.5(5) . . . . ?
N5 C22 C23 C24 -0.8(5) . . . . ?
C21 C22 C23 C24 178.4(3) . . . . ?
C22 C23 C24 C25 -1.8(6) . . . . ?
C23 C24 C25 C26 2.1(6) . . . . ?
C22 N5 C26 C25 -2.7(6) . . . . ?
Mn1 N5 C26 C25 170.8(3) . . . . ?
C24 C25 C26 N5 0.2(6) . . . . ?

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
O1 H1 O2 0.87 1.94 2.785(4) 163.6 .
O1 H1 O2A 0.87 2.11 2.911(18) 152.9 .

_refine_diff_density_max         0.516
_refine_diff_density_min         -0.808
_refine_diff_density_rms         0.082

####################################################################### 
# 
# 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_9
_database_code_depnum_ccdc_archive 'CCDC 1470086'
_audit_update_record             
;
2016-03-22 deposited with the CCDC.
2016-05-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            aja073x
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H22 Fe N6 O, C2 H3 N, 2(Cl O4)'
_chemical_formula_sum            'C30 H25 Cl2 Fe N7 O9'
_chemical_formula_weight         754.32

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'
Fe Fe 0.3463 0.8444 '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                   10.1576(2)
_cell_length_b                   11.9556(3)
_cell_length_c                   15.5564(5)
_cell_angle_alpha                95.1700(10)
_cell_angle_beta                 100.1480(10)
_cell_angle_gamma                93.0010(10)
_cell_volume                     1847.56(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    26335
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.485

_exptl_crystal_description       prism
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             772
_exptl_absorpt_coefficient_mu    0.610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.842
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_process_details   'Sortav (Blessing, 1995)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(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  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            29866
_diffrn_reflns_av_R_equivalents  0.0998
_diffrn_reflns_av_sigmaI/netI    0.0828
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         27.38
_reflns_number_total             8315
_reflns_number_gt                5864
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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 > 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)+(0.1249P)²+1.3546P] 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         8315
_refine_ls_number_parameters     445
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1061
_refine_ls_R_factor_gt           0.0759
_refine_ls_wR_factor_ref         0.2257
_refine_ls_wR_factor_gt          0.2089
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
C1 C 0.6052(4) 0.4956(3) 0.8217(3) 0.0348(9) Uani 1 1 d . . .
C2 C 0.7272(4) 0.4962(3) 0.7744(3) 0.0335(9) Uani 1 1 d . . .
C3 C 0.8338(4) 0.5740(4) 0.7985(3) 0.0420(10) Uani 1 1 d . . .
H3 H 0.8368 0.6283 0.8474 0.050 Uiso 1 1 calc R . .
C4 C 0.9375(4) 0.5735(4) 0.7514(3) 0.0449(11) Uani 1 1 d . . .
H4 H 1.0112 0.6282 0.7669 0.054 Uiso 1 1 calc R . .
C5 C 0.9323(4) 0.4924(4) 0.6814(3) 0.0438(10) Uani 1 1 d . . .
H5 H 1.0023 0.4902 0.6482 0.053 Uiso 1 1 calc R . .
C6 C 0.8233(4) 0.4144(3) 0.6608(3) 0.0345(9) Uani 1 1 d . . .
H6 H 0.8195 0.3585 0.6128 0.041 Uiso 1 1 calc R . .
C7 C 0.5919(4) 0.3849(3) 0.8621(3) 0.0339(9) Uani 1 1 d . . .
C8 C 0.5904(5) 0.3772(4) 0.9498(3) 0.0445(11) Uani 1 1 d . . .
H8 H 0.6096 0.4423 0.9909 0.053 Uiso 1 1 calc R . .
C9 C 0.5602(5) 0.2728(4) 0.9772(3) 0.0506(12) Uani 1 1 d . . .
H9 H 0.5656 0.2642 1.0378 0.061 Uiso 1 1 calc R . .
C10 C 0.5218(6) 0.1807(4) 0.9138(3) 0.0544(13) Uani 1 1 d . . .
H10 H 0.4959 0.1096 0.9307 0.065 Uiso 1 1 calc R . .
C11 C 0.5218(5) 0.1939(4) 0.8274(3) 0.0453(11) Uani 1 1 d . . .
C12 C 0.4460(5) 0.1192(4) 0.7497(3) 0.0433(10) Uani 1 1 d . . .
C13 C 0.3837(5) 0.0153(4) 0.7554(4) 0.0492(12) Uani 1 1 d . . .
H13 H 0.4005 -0.0189 0.8088 0.059 Uiso 1 1 calc R . .
C14 C 0.2970(5) -0.0390(4) 0.6835(4) 0.0528(12) Uani 1 1 d . . .
H14 H 0.2535 -0.1105 0.6864 0.063 Uiso 1 1 calc R . .
C15 C 0.2755(5) 0.0136(4) 0.6072(3) 0.0492(12) Uani 1 1 d . . .
H15 H 0.2127 -0.0190 0.5575 0.059 Uiso 1 1 calc R . .
C16 C 0.3480(5) 0.1156(4) 0.6045(3) 0.0460(11) Uani 1 1 d . . .
H16 H 0.3366 0.1481 0.5504 0.055 Uiso 1 1 calc R . .
C17 C 0.4786(4) 0.5048(3) 0.7523(3) 0.0337(9) Uani 1 1 d . . .
C18 C 0.3920(4) 0.5901(4) 0.7545(3) 0.0391(10) Uani 1 1 d . . .
H18 H 0.4009 0.6435 0.8046 0.047 Uiso 1 1 calc R . .
C19 C 0.2919(4) 0.5960(4) 0.6822(3) 0.0422(10) Uani 1 1 d . . .
H19 H 0.2270 0.6501 0.6843 0.051 Uiso 1 1 calc R . .
C20 C 0.2864(4) 0.5234(3) 0.6069(3) 0.0387(10) Uani 1 1 d . . .
H20 H 0.2227 0.5307 0.5555 0.046 Uiso 1 1 calc R . .
C21 C 0.3753(4) 0.4407(3) 0.6084(3) 0.0339(9) Uani 1 1 d . . .
C22 C 0.4011(4) 0.3666(3) 0.5329(3) 0.0330(9) Uani 1 1 d . . .
C23 C 0.3221(4) 0.3577(4) 0.4496(3) 0.0407(10) Uani 1 1 d . . .
H23 H 0.2436 0.3979 0.4386 0.049 Uiso 1 1 calc R . .
C24 C 0.3602(5) 0.2890(4) 0.3831(3) 0.0487(11) Uani 1 1 d . . .
H24 H 0.3081 0.2821 0.3256 0.058 Uiso 1 1 calc R . .
C25 C 0.4739(5) 0.2308(4) 0.4004(3) 0.0482(11) Uani 1 1 d . . .
H25 H 0.5010 0.1834 0.3553 0.058 Uiso 1 1 calc R . .
C26 C 0.5477(4) 0.2426(4) 0.4848(3) 0.0421(10) Uani 1 1 d . . .
H26 H 0.6269 0.2033 0.4962 0.051 Uiso 1 1 calc R . .
C27 C 0.7707(5) 0.1182(4) 0.6679(3) 0.0487(11) Uani 1 1 d . . .
C28 C 0.8691(7) 0.0363(6) 0.6611(4) 0.0764(19) Uani 1 1 d . . .
H28A H 0.8235 -0.0365 0.6355 0.115 Uiso 1 1 calc R . .
H28B H 0.9200 0.0284 0.7196 0.115 Uiso 1 1 calc R . .
H28C H 0.9303 0.0614 0.6234 0.115 Uiso 1 1 calc R . .
C29 C 0.1075(9) 0.9716(7) 0.8906(6) 0.108(3) Uani 1 1 d . . .
H29A H 0.1437 1.0338 0.8629 0.162 Uiso 1 1 calc R . .
H29B H 0.1295 0.9880 0.9546 0.162 Uiso 1 1 calc R . .
H29C H 0.0099 0.9625 0.8720 0.162 Uiso 1 1 calc R . .
C30 C 0.1667(6) 0.8670(6) 0.8643(4) 0.0678(16) Uani 1 1 d . . .
N1 N 0.7216(3) 0.4153(3) 0.7068(2) 0.0302(7) Uani 1 1 d . . .
N2 N 0.5682(3) 0.2937(3) 0.8031(2) 0.0318(7) Uani 1 1 d . . .
N3 N 0.4319(3) 0.1702(3) 0.6725(2) 0.0355(8) Uani 1 1 d . . .
N4 N 0.4624(3) 0.4276(3) 0.6827(2) 0.0326(7) Uani 1 1 d . . .
N5 N 0.5122(3) 0.3080(3) 0.5521(2) 0.0333(7) Uani 1 1 d . . .
N6 N 0.6928(3) 0.1830(3) 0.6705(2) 0.0307(7) Uani 1 1 d . . .
N7 N 0.2081(5) 0.7874(5) 0.8420(3) 0.0707(14) Uani 1 1 d . . .
O1 O 0.6199(3) 0.5821(3) 0.89048(19) 0.0427(7) Uani 1 1 d . . .
H1 H 0.6319 0.6443 0.8710 0.064 Uiso 1 1 calc R . .
O2 O 0.8116(5) -0.1615(4) 0.9122(4) 0.112(2) Uani 1 1 d . . .
O3 O 0.7160(6) -0.0375(4) 0.8148(4) 0.1051(18) Uani 1 1 d . . .
O4 O 0.6080(5) -0.2119(3) 0.8233(3) 0.0751(12) Uani 1 1 d . . .
O5 O 0.6238(5) -0.0668(4) 0.9344(3) 0.0887(15) Uani 1 1 d . . .
O6 O 1.0742(7) 0.1734(6) 0.5070(5) 0.143(3) Uani 1 1 d . . .
O7 O 0.8565(4) 0.2225(4) 0.4903(3) 0.0828(14) Uani 1 1 d . . .
O8 O 1.0206(5) 0.3625(4) 0.5008(4) 0.111(2) Uani 1 1 d . . .
O9 O 0.9825(5) 0.2337(4) 0.3799(3) 0.0910(14) Uani 1 1 d . . .
Cl1 Cl 0.68983(13) -0.11721(9) 0.86950(8) 0.0517(3) Uani 1 1 d . . .
Cl2 Cl 0.98595(9) 0.24777(8) 0.47226(7) 0.0380(3) Uani 1 1 d . . .
Fe1 Fe 0.56867(5) 0.30094(4) 0.67986(3) 0.02788(18) 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 O1 1.402(5) . ?
C1 C7 1.525(6) . ?
C1 C17 1.542(6) . ?
C1 C2 1.549(6) . ?
C2 N1 1.354(5) . ?
C2 C3 1.366(6) . ?
C3 C4 1.385(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(6) . ?
C5 H5 0.9500 . ?
C6 N1 1.358(5) . ?
C6 H6 0.9500 . ?
C7 N2 1.343(5) . ?
C7 C8 1.378(6) . ?
C8 C9 1.392(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.400(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.369(6) . ?
C10 H10 0.9500 . ?
C11 N2 1.369(6) . ?
C11 C12 1.502(7) . ?
C12 N3 1.384(6) . ?
C12 C13 1.382(6) . ?
C13 C14 1.382(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.399(6) . ?
C15 H15 0.9500 . ?
C16 N3 1.331(6) . ?
C16 H16 0.9500 . ?
C17 N4 1.339(5) . ?
C17 C18 1.383(5) . ?
C18 C19 1.387(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.385(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.373(5) . ?
C20 H20 0.9500 . ?
C21 N4 1.352(5) . ?
C21 C22 1.476(6) . ?
C22 N5 1.362(5) . ?
C22 C23 1.391(6) . ?
C23 C24 1.384(7) . ?
C23 H23 0.9500 . ?
C24 C25 1.378(7) . ?
C24 H24 0.9500 . ?
C25 C26 1.383(6) . ?
C25 H25 0.9500 . ?
C26 N5 1.362(6) . ?
C26 H26 0.9500 . ?
C27 N6 1.139(6) . ?
C27 C28 1.445(7) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C30 1.472(10) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 N7 1.111(8) . ?
N1 Fe1 1.976(3) . ?
N2 Fe1 1.927(3) . ?
N3 Fe1 2.017(3) . ?
N4 Fe1 1.907(3) . ?
N5 Fe1 1.979(3) . ?
N6 Fe1 1.953(3) . ?
O1 H1 0.8400 . ?
O2 Cl1 1.447(5) . ?
O3 Cl1 1.379(4) . ?
O4 Cl1 1.426(4) . ?
O5 Cl1 1.416(4) . ?
O6 Cl2 1.373(5) . ?
O7 Cl2 1.415(4) . ?
O8 Cl2 1.410(4) . ?
O9 Cl2 1.425(4) . ?

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 C1 C7 106.9(3) . . ?
O1 C1 C17 111.9(3) . . ?
C7 C1 C17 108.8(3) . . ?
O1 C1 C2 111.8(3) . . ?
C7 C1 C2 109.7(3) . . ?
C17 C1 C2 107.8(3) . . ?
N1 C2 C3 121.7(4) . . ?
N1 C2 C1 115.9(3) . . ?
C3 C2 C1 122.4(4) . . ?
C2 C3 C4 119.9(4) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 119.1(4) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 118.8(4) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
N1 C6 C5 122.1(4) . . ?
N1 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
N2 C7 C8 121.6(4) . . ?
N2 C7 C1 114.0(3) . . ?
C8 C7 C1 124.2(4) . . ?
C7 C8 C9 119.0(4) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C8 C9 C10 118.7(4) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C11 C10 C9 119.5(5) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 N2 120.6(5) . . ?
C10 C11 C12 126.3(5) . . ?
N2 C11 C12 111.5(4) . . ?
N3 C12 C13 122.7(4) . . ?
N3 C12 C11 113.0(4) . . ?
C13 C12 C11 123.9(4) . . ?
C14 C13 C12 120.0(5) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 118.1(4) . . ?
C13 C14 H14 120.9 . . ?
C15 C14 H14 120.9 . . ?
C14 C15 C16 118.8(4) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
N3 C16 C15 124.5(4) . . ?
N3 C16 H16 117.7 . . ?
C15 C16 H16 117.7 . . ?
N4 C17 C18 120.2(4) . . ?
N4 C17 C1 114.7(3) . . ?
C18 C17 C1 124.9(4) . . ?
C17 C18 C19 118.7(4) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
C18 C19 C20 120.2(4) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C21 C20 C19 118.4(4) . . ?
C21 C20 H20 120.8 . . ?
C19 C20 H20 120.8 . . ?
N4 C21 C20 120.8(4) . . ?
N4 C21 C22 111.7(3) . . ?
C20 C21 C22 127.2(4) . . ?
N5 C22 C23 122.6(4) . . ?
N5 C22 C21 113.3(3) . . ?
C23 C22 C21 124.0(4) . . ?
C24 C23 C22 118.6(4) . . ?
C24 C23 H23 120.7 . . ?
C22 C23 H23 120.7 . . ?
C25 C24 C23 119.9(4) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 118.7(4) . . ?
C24 C25 H25 120.6 . . ?
C26 C25 H25 120.6 . . ?
N5 C26 C25 123.0(4) . . ?
N5 C26 H26 118.5 . . ?
C25 C26 H26 118.5 . . ?
N6 C27 C28 177.8(5) . . ?
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 . . ?
C30 C29 H29A 109.5 . . ?
C30 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C30 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N7 C30 C29 177.7(7) . . ?
C2 N1 C6 118.5(4) . . ?
C2 N1 Fe1 119.4(3) . . ?
C6 N1 Fe1 122.1(3) . . ?
C7 N2 C11 119.4(4) . . ?
C7 N2 Fe1 122.8(3) . . ?
C11 N2 Fe1 117.0(3) . . ?
C16 N3 C12 115.6(4) . . ?
C16 N3 Fe1 131.4(3) . . ?
C12 N3 Fe1 111.9(3) . . ?
C17 N4 C21 120.8(3) . . ?
C17 N4 Fe1 122.2(3) . . ?
C21 N4 Fe1 116.8(3) . . ?
C26 N5 C22 117.1(4) . . ?
C26 N5 Fe1 128.4(3) . . ?
C22 N5 Fe1 112.4(3) . . ?
C27 N6 Fe1 176.1(4) . . ?
C1 O1 H1 109.5 . . ?
O3 Cl1 O5 108.7(3) . . ?
O3 Cl1 O4 112.3(3) . . ?
O5 Cl1 O4 109.1(3) . . ?
O3 Cl1 O2 111.7(4) . . ?
O5 Cl1 O2 108.9(3) . . ?
O4 Cl1 O2 106.0(3) . . ?
O6 Cl2 O8 116.0(5) . . ?
O6 Cl2 O7 110.7(4) . . ?
O8 Cl2 O7 107.2(3) . . ?
O6 Cl2 O9 105.7(4) . . ?
O8 Cl2 O9 107.4(3) . . ?
O7 Cl2 O9 109.8(3) . . ?
N4 Fe1 N2 89.14(13) . . ?
N4 Fe1 N6 172.79(14) . . ?
N2 Fe1 N6 95.21(13) . . ?
N4 Fe1 N1 84.31(13) . . ?
N2 Fe1 N1 91.06(14) . . ?
N6 Fe1 N1 89.84(13) . . ?
N4 Fe1 N5 80.74(14) . . ?
N2 Fe1 N5 163.30(14) . . ?
N6 Fe1 N5 96.30(13) . . ?
N1 Fe1 N5 101.03(13) . . ?
N4 Fe1 N3 102.63(14) . . ?
N2 Fe1 N3 80.33(14) . . ?
N6 Fe1 N3 83.81(14) . . ?
N1 Fe1 N3 168.76(13) . . ?
N5 Fe1 N3 88.91(14) . . ?

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 C1 C2 N1 180.0(3) . . . . ?
C7 C1 C2 N1 61.6(4) . . . . ?
C17 C1 C2 N1 -56.7(4) . . . . ?
O1 C1 C2 C3 -0.6(5) . . . . ?
C7 C1 C2 C3 -119.0(4) . . . . ?
C17 C1 C2 C3 122.7(4) . . . . ?
N1 C2 C3 C4 2.2(6) . . . . ?
C1 C2 C3 C4 -177.2(4) . . . . ?
C2 C3 C4 C5 -1.2(6) . . . . ?
C3 C4 C5 C6 0.1(7) . . . . ?
C4 C5 C6 N1 0.1(6) . . . . ?
O1 C1 C7 N2 175.9(3) . . . . ?
C17 C1 C7 N2 55.0(4) . . . . ?
C2 C1 C7 N2 -62.7(4) . . . . ?
O1 C1 C7 C8 2.2(6) . . . . ?
C17 C1 C7 C8 -118.7(4) . . . . ?
C2 C1 C7 C8 123.6(4) . . . . ?
N2 C7 C8 C9 -1.6(7) . . . . ?
C1 C7 C8 C9 171.6(4) . . . . ?
C7 C8 C9 C10 -5.1(7) . . . . ?
C8 C9 C10 C11 3.5(7) . . . . ?
C9 C10 C11 N2 4.8(7) . . . . ?
C9 C10 C11 C12 -159.7(5) . . . . ?
C10 C11 C12 N3 161.5(4) . . . . ?
N2 C11 C12 N3 -4.2(5) . . . . ?
C10 C11 C12 C13 -11.8(7) . . . . ?
N2 C11 C12 C13 -177.5(4) . . . . ?
N3 C12 C13 C14 -3.9(7) . . . . ?
C11 C12 C13 C14 168.7(4) . . . . ?
C12 C13 C14 C15 0.0(7) . . . . ?
C13 C14 C15 C16 3.8(7) . . . . ?
C14 C15 C16 N3 -4.2(8) . . . . ?
O1 C1 C17 N4 176.9(3) . . . . ?
C7 C1 C17 N4 -65.3(4) . . . . ?
C2 C1 C17 N4 53.6(4) . . . . ?
O1 C1 C17 C18 2.6(6) . . . . ?
C7 C1 C17 C18 120.5(4) . . . . ?
C2 C1 C17 C18 -120.7(4) . . . . ?
N4 C17 C18 C19 -2.2(6) . . . . ?
C1 C17 C18 C19 171.7(4) . . . . ?
C17 C18 C19 C20 -5.2(6) . . . . ?
C18 C19 C20 C21 5.0(6) . . . . ?
C19 C20 C21 N4 2.6(6) . . . . ?
C19 C20 C21 C22 -169.7(4) . . . . ?
N4 C21 C22 N5 -4.8(5) . . . . ?
C20 C21 C22 N5 168.1(4) . . . . ?
N4 C21 C22 C23 176.1(4) . . . . ?
C20 C21 C22 C23 -10.9(7) . . . . ?
N5 C22 C23 C24 -1.9(6) . . . . ?
C21 C22 C23 C24 177.0(4) . . . . ?
C22 C23 C24 C25 0.4(7) . . . . ?
C23 C24 C25 C26 0.0(7) . . . . ?
C24 C25 C26 N5 1.0(8) . . . . ?
C3 C2 N1 C6 -2.0(5) . . . . ?
C1 C2 N1 C6 177.5(3) . . . . ?
C3 C2 N1 Fe1 176.8(3) . . . . ?
C1 C2 N1 Fe1 -3.8(4) . . . . ?
C5 C6 N1 C2 0.8(6) . . . . ?
C5 C6 N1 Fe1 -177.9(3) . . . . ?
C8 C7 N2 C11 10.0(6) . . . . ?
C1 C7 N2 C11 -163.9(4) . . . . ?
C8 C7 N2 Fe1 179.7(3) . . . . ?
C1 C7 N2 Fe1 5.8(5) . . . . ?
C10 C11 N2 C7 -11.6(6) . . . . ?
C12 C11 N2 C7 155.0(4) . . . . ?
C10 C11 N2 Fe1 178.1(4) . . . . ?
C12 C11 N2 Fe1 -15.3(4) . . . . ?
C15 C16 N3 C12 0.4(6) . . . . ?
C15 C16 N3 Fe1 168.0(4) . . . . ?
C13 C12 N3 C16 3.6(6) . . . . ?
C11 C12 N3 C16 -169.8(4) . . . . ?
C13 C12 N3 Fe1 -166.3(4) . . . . ?
C11 C12 N3 Fe1 20.3(4) . . . . ?
C18 C17 N4 C21 10.0(6) . . . . ?
C1 C17 N4 C21 -164.5(4) . . . . ?
C18 C17 N4 Fe1 -174.5(3) . . . . ?
C1 C17 N4 Fe1 11.0(5) . . . . ?
C20 C21 N4 C17 -10.2(6) . . . . ?
C22 C21 N4 C17 163.2(3) . . . . ?
C20 C21 N4 Fe1 174.0(3) . . . . ?
C22 C21 N4 Fe1 -12.5(4) . . . . ?
C25 C26 N5 C22 -2.4(7) . . . . ?
C25 C26 N5 Fe1 159.7(4) . . . . ?
C23 C22 N5 C26 2.9(6) . . . . ?
C21 C22 N5 C26 -176.2(4) . . . . ?
C23 C22 N5 Fe1 -162.1(3) . . . . ?
C21 C22 N5 Fe1 18.9(4) . . . . ?
C17 N4 Fe1 N2 35.8(3) . . . . ?
C21 N4 Fe1 N2 -148.5(3) . . . . ?
C17 N4 Fe1 N1 -55.4(3) . . . . ?
C21 N4 Fe1 N1 120.3(3) . . . . ?
C17 N4 Fe1 N5 -157.5(3) . . . . ?
C21 N4 Fe1 N5 18.1(3) . . . . ?
C17 N4 Fe1 N3 115.7(3) . . . . ?
C21 N4 Fe1 N3 -68.7(3) . . . . ?
C7 N2 Fe1 N4 -45.9(3) . . . . ?
C11 N2 Fe1 N4 124.0(3) . . . . ?
C7 N2 Fe1 N6 128.3(3) . . . . ?
C11 N2 Fe1 N6 -61.8(3) . . . . ?
C7 N2 Fe1 N1 38.4(3) . . . . ?
C11 N2 Fe1 N1 -151.7(3) . . . . ?
C7 N2 Fe1 N5 -98.3(5) . . . . ?
C11 N2 Fe1 N5 71.6(6) . . . . ?
C7 N2 Fe1 N3 -148.9(3) . . . . ?
C11 N2 Fe1 N3 21.0(3) . . . . ?
C2 N1 Fe1 N4 50.4(3) . . . . ?
C6 N1 Fe1 N4 -130.9(3) . . . . ?
C2 N1 Fe1 N2 -38.6(3) . . . . ?
C6 N1 Fe1 N2 140.1(3) . . . . ?
C2 N1 Fe1 N6 -133.8(3) . . . . ?
C6 N1 Fe1 N6 44.9(3) . . . . ?
C2 N1 Fe1 N5 129.8(3) . . . . ?
C6 N1 Fe1 N5 -51.5(3) . . . . ?
C2 N1 Fe1 N3 -78.3(7) . . . . ?
C6 N1 Fe1 N3 100.4(7) . . . . ?
C26 N5 Fe1 N4 177.1(4) . . . . ?
C22 N5 Fe1 N4 -20.1(3) . . . . ?
C26 N5 Fe1 N2 -129.6(5) . . . . ?
C22 N5 Fe1 N2 33.2(6) . . . . ?
C26 N5 Fe1 N6 3.7(4) . . . . ?
C22 N5 Fe1 N6 166.5(3) . . . . ?
C26 N5 Fe1 N1 94.8(4) . . . . ?
C22 N5 Fe1 N1 -102.4(3) . . . . ?
C26 N5 Fe1 N3 -79.9(4) . . . . ?
C22 N5 Fe1 N3 82.9(3) . . . . ?
C16 N3 Fe1 N4 82.8(4) . . . . ?
C12 N3 Fe1 N4 -109.3(3) . . . . ?
C16 N3 Fe1 N2 169.7(4) . . . . ?
C12 N3 Fe1 N2 -22.4(3) . . . . ?
C16 N3 Fe1 N6 -93.9(4) . . . . ?
C12 N3 Fe1 N6 74.0(3) . . . . ?
C16 N3 Fe1 N1 -149.9(6) . . . . ?
C12 N3 Fe1 N1 18.0(8) . . . . ?
C16 N3 Fe1 N5 2.5(4) . . . . ?
C12 N3 Fe1 N5 170.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.38
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.482
_refine_diff_density_min         -0.766
_refine_diff_density_rms         0.099

# SQUEEZE RESULTS (APPEND TO CIF)
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.000 0.500 1.000 344.4 20.2
_platon_squeeze_details          
; 
?
;
####################################################################### 
# 
# 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_10
_database_code_depnum_ccdc_archive 'CCDC 1470087'
_audit_update_record             
;
2016-03-22 deposited with the CCDC.
2016-05-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C56 H46 Cl4 Co2 N12 O19'
_chemical_formula_weight         1450.71

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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   14.0840(2)
_cell_length_b                   21.3004(3)
_cell_length_c                   19.6325(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.2450(10)
_cell_angle_gamma                90
_cell_volume                     5873.49(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    46403
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.485

_exptl_crystal_description       block
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_F_000             2960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.420
_exptl_absorpt_coefficient_mu    0.835
_shelx_estimated_absorpt_T_min   0.705
_shelx_estimated_absorpt_T_max   0.721
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.691
_exptl_absorpt_correction_T_max  0.742
_exptl_absorpt_process_details   'Sortav (Blessing, 1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'profile from ω scans'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            78539
_diffrn_reflns_av_unetI/netI     0.1317
_diffrn_reflns_av_R_equivalents  0.1788
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.052
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             13449
_reflns_number_gt                6984
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
HKL Denzo and Scalepack (Otwinowski & Minor 19
;
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0710P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         13449
_refine_ls_number_parameters     908
_refine_ls_number_restraints     184
_refine_ls_R_factor_all          0.1502
_refine_ls_R_factor_gt           0.0640
_refine_ls_wR_factor_ref         0.1689
_refine_ls_wR_factor_gt          0.1382
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.026
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.09543(4) 0.66060(2) 0.66426(3) 0.03218(17) Uani 1 1 d . . . . .
H1O H 0.232(12) 0.776(3) 0.968(9) 0.43(11) Uiso 1 1 d D . . . .
Co2 Co 0.60880(4) 0.60286(2) 0.80816(3) 0.02963(16) Uani 1 1 d . . . . .
H2O H 0.173(9) 0.730(6) 0.983(7) 0.32(8) Uiso 1 1 d D . . . .
Cl1 Cl 0.35575(8) 0.91741(6) 0.93187(6) 0.0471(3) Uani 1 1 d . . . . .
Cl2 Cl 0.14435(8) 0.89601(6) 0.56779(6) 0.0466(3) Uani 1 1 d . . . . .
Cl3 Cl 0.86713(8) 0.88897(7) 0.88232(8) 0.0616(4) Uani 1 1 d . . . . .
Cl4 Cl 0.64653(8) 0.88604(6) 0.61344(7) 0.0503(3) Uani 1 1 d . . . . .
O1 O 0.30488(19) 0.72662(15) 0.83874(16) 0.0467(8) Uani 1 1 d D . . . .
H1 H 0.2767(10) 0.730(2) 0.8754(11) 0.070 Uiso 1 1 calc DR U . . .
O2 O 0.80524(19) 0.75760(13) 0.73847(15) 0.0393(7) Uani 1 1 d D . . . .
H2 H 0.822(3) 0.7807(15) 0.7696(10) 0.059 Uiso 1 1 calc DR U . . .
O3 O 0.3569(3) 0.9202(2) 0.86061(19) 0.0856(13) Uani 1 1 d . U . . .
O4 O 0.4416(3) 0.8922(2) 0.9616(2) 0.0997(16) Uani 1 1 d . U . . .
O5 O 0.3457(2) 0.97958(14) 0.95937(18) 0.0599(10) Uani 1 1 d . U . . .
O6 O 0.2747(3) 0.88096(16) 0.94891(19) 0.0757(12) Uani 1 1 d . U . . .
O7 O 0.1806(6) 0.8459(5) 0.6140(6) 0.110(4) Uani 0.608(10) 1 d D U P A 1
O8 O 0.0665(6) 0.9254(3) 0.5979(6) 0.085(3) Uani 0.608(10) 1 d D U P A 1
O9 O 0.1055(6) 0.8624(5) 0.5099(4) 0.091(3) Uani 0.608(10) 1 d D U P A 1
O7A O 0.1757(12) 0.8335(6) 0.5684(9) 0.094(4) Uani 0.392(10) 1 d D U P A 2
O8A O 0.1265(11) 0.9140(6) 0.6326(6) 0.080(4) Uani 0.392(10) 1 d D U P A 2
O9A O 0.0752(9) 0.9084(9) 0.5176(8) 0.114(5) Uani 0.392(10) 1 d D U P A 2
O10 O 0.2214(2) 0.93515(16) 0.5524(2) 0.0704(11) Uani 1 1 d . . . . .
O11 O 0.8730(3) 0.82296(16) 0.8597(2) 0.0699(10) Uani 1 1 d . . . . .
O12 O 0.9552(2) 0.90254(19) 0.9208(2) 0.0799(12) Uani 1 1 d . . . . .
O13 O 0.8539(3) 0.9278(2) 0.8243(2) 0.0905(13) Uani 1 1 d . . . . .
O14 O 0.7895(2) 0.89510(18) 0.9244(2) 0.0795(12) Uani 1 1 d . . . . .
O15 O 0.6241(5) 0.8225(2) 0.6090(4) 0.091(2) Uani 0.834(10) 1 d D U P B 1
O16 O 0.5672(4) 0.9207(3) 0.6355(3) 0.0775(18) Uani 0.834(10) 1 d D U P B 1
O17 O 0.6680(3) 0.9088(3) 0.5487(3) 0.087(2) Uani 0.834(10) 1 d D U P B 1
O15A O 0.591(2) 0.8354(13) 0.6410(16) 0.082(6) Uani 0.166(10) 1 d D U P B 2
O16A O 0.604(2) 0.9388(10) 0.6097(16) 0.075(6) Uani 0.166(10) 1 d D U P B 2
O17A O 0.6691(18) 0.8582(16) 0.5478(13) 0.090(6) Uani 0.166(10) 1 d D U P B 2
O18 O 0.7282(2) 0.8946(2) 0.6606(2) 0.0845(13) Uani 1 1 d . . . . .
O19 O 0.2191(4) 0.7380(2) 0.9571(2) 0.0848(13) Uani 1 1 d D . . . .
N1 N 0.2464(2) 0.68158(15) 0.66465(18) 0.0355(9) Uani 1 1 d . . . . .
N2 N 0.0963(2) 0.74402(15) 0.72106(18) 0.0328(8) Uani 1 1 d . . . . .
N3 N 0.0027(2) 0.72145(16) 0.60394(19) 0.0401(9) Uani 1 1 d . . . . .
N4 N 0.1277(2) 0.62016(15) 0.76050(17) 0.0308(8) Uani 1 1 d . . . . .
N5 N -0.0244(2) 0.59661(15) 0.68212(18) 0.0320(8) Uani 1 1 d . . . . .
N6 N 0.1129(2) 0.59575(18) 0.5857(2) 0.0427(10) Uani 1 1 d . . . . .
N7 N 0.7568(2) 0.61616(15) 0.83470(17) 0.0312(8) Uani 1 1 d . . . . .
N8 N 0.6339(2) 0.63370(14) 0.70940(17) 0.0298(8) Uani 1 1 d . . . . .
N9 N 0.4850(2) 0.56975(15) 0.74027(18) 0.0335(8) Uani 1 1 d . . . . .
N10 N 0.6115(2) 0.69963(15) 0.83171(17) 0.0328(8) Uani 1 1 d . . . . .
N11 N 0.5225(2) 0.61014(17) 0.89143(18) 0.0365(9) Uani 1 1 d . . . . .
N12 N 0.6304(2) 0.50449(16) 0.81275(18) 0.0362(9) Uani 1 1 d . . . . .
C1 C 0.2399(3) 0.70691(19) 0.7861(2) 0.0354(10) Uani 1 1 d . . . . .
C2 C 0.2937(3) 0.70463(18) 0.7212(2) 0.0343(10) Uani 1 1 d . . . . .
C3 C 0.3869(3) 0.72678(19) 0.7211(3) 0.0411(11) Uani 1 1 d . . . . .
H3 H 0.4195 0.7423 0.7617 0.049 Uiso 1 1 calc R U . . .
C4 C 0.4306(3) 0.7256(2) 0.6604(3) 0.0471(13) Uani 1 1 d . . . . .
H4 H 0.4931 0.7420 0.6585 0.057 Uiso 1 1 calc R U . . .
C5 C 0.3844(3) 0.7011(2) 0.6035(3) 0.0456(13) Uani 1 1 d . . . . .
H5 H 0.4149 0.6988 0.5620 0.055 Uiso 1 1 calc R U . . .
C6 C 0.2920(3) 0.6793(2) 0.6067(2) 0.0414(11) Uani 1 1 d . . . . .
H6 H 0.2598 0.6621 0.5667 0.050 Uiso 1 1 calc R U . . .
C7 C 0.1585(3) 0.75462(18) 0.7742(2) 0.0343(10) Uani 1 1 d . . . . .
C8 C 0.1537(3) 0.8085(2) 0.8134(2) 0.0428(11) Uani 1 1 d . . . . .
H8 H 0.1999 0.8170 0.8500 0.051 Uiso 1 1 calc R U . . .
C9 C 0.0789(3) 0.8497(2) 0.7972(3) 0.0495(13) Uani 1 1 d . . . . .
H9 H 0.0711 0.8854 0.8252 0.059 Uiso 1 1 calc R U . . .
C10 C 0.0167(3) 0.8397(2) 0.7417(3) 0.0454(12) Uani 1 1 d . . . . .
H10 H -0.0335 0.8685 0.7305 0.054 Uiso 1 1 calc R U . . .
C11 C 0.0279(3) 0.78685(19) 0.7021(2) 0.0358(11) Uani 1 1 d . . . . .
C12 C -0.0231(3) 0.7741(2) 0.6364(2) 0.0360(10) Uani 1 1 d . . . . .
C13 C -0.0917(3) 0.8148(2) 0.6055(3) 0.0495(13) Uani 1 1 d . . . . .
H13 H -0.1103 0.8514 0.6289 0.059 Uiso 1 1 calc R U . . .
C14 C -0.1323(3) 0.8014(2) 0.5408(3) 0.0535(14) Uani 1 1 d . . . . .
H14 H -0.1795 0.8283 0.5196 0.064 Uiso 1 1 calc R U . . .
C15 C -0.1034(3) 0.7487(3) 0.5078(3) 0.0541(13) Uani 1 1 d . . . . .
H15 H -0.1290 0.7390 0.4629 0.065 Uiso 1 1 calc R U . . .
C16 C -0.0367(3) 0.7105(2) 0.5410(2) 0.0471(12) Uani 1 1 d . . . . .
H16 H -0.0173 0.6739 0.5180 0.057 Uiso 1 1 calc R U . . .
C17 C 0.2001(3) 0.64196(19) 0.8022(2) 0.0327(10) Uani 1 1 d . . . . .
C18 C 0.2347(3) 0.6077(2) 0.8593(2) 0.0395(11) Uani 1 1 d . . . . .
H18 H 0.2859 0.6234 0.8886 0.047 Uiso 1 1 calc R U . . .
C19 C 0.1936(3) 0.5508(2) 0.8725(2) 0.0429(11) Uani 1 1 d . . . . .
H19 H 0.2187 0.5257 0.9095 0.051 Uiso 1 1 calc R U . . .
C20 C 0.1157(3) 0.5304(2) 0.8317(2) 0.0384(11) Uani 1 1 d . . . . .
H20 H 0.0854 0.4919 0.8411 0.046 Uiso 1 1 calc R U . . .
C21 C 0.0825(3) 0.56687(18) 0.7770(2) 0.0316(10) Uani 1 1 d . . . . .
C22 C -0.0064(3) 0.55615(18) 0.7339(2) 0.0309(10) Uani 1 1 d . . . . .
C23 C -0.0717(3) 0.50931(19) 0.7501(2) 0.0374(11) Uani 1 1 d . . . . .
H23 H -0.0577 0.4814 0.7872 0.045 Uiso 1 1 calc R U . . .
C24 C -0.1563(3) 0.5050(2) 0.7106(3) 0.0440(12) Uani 1 1 d . . . . .
H24 H -0.2018 0.4740 0.7205 0.053 Uiso 1 1 calc R U . . .
C25 C -0.1749(3) 0.5456(2) 0.6568(3) 0.0445(12) Uani 1 1 d . . . . .
H25 H -0.2327 0.5430 0.6288 0.053 Uiso 1 1 calc R U . . .
C26 C -0.1066(3) 0.59060(19) 0.6445(2) 0.0375(11) Uani 1 1 d . . . . .
H26 H -0.1192 0.6186 0.6073 0.045 Uiso 1 1 calc R U . . .
C27 C 0.1183(3) 0.5610(2) 0.5433(3) 0.0406(11) Uani 1 1 d . . . . .
C28 C 0.1248(3) 0.5152(2) 0.4875(2) 0.0492(12) Uani 1 1 d . . . . .
H28A H 0.0953 0.5328 0.4449 0.074 Uiso 1 1 calc R U . . .
H28B H 0.0915 0.4765 0.4986 0.074 Uiso 1 1 calc R U . . .
H28C H 0.1919 0.5057 0.4818 0.074 Uiso 1 1 calc R U . . .
C29 C 0.7450(3) 0.71113(18) 0.7620(2) 0.0335(10) Uani 1 1 d . . . . .
C30 C 0.8026(3) 0.66643(19) 0.8103(2) 0.0303(9) Uani 1 1 d . . . . .
C31 C 0.8977(3) 0.6781(2) 0.8310(2) 0.0376(11) Uani 1 1 d . . . . .
H31 H 0.9302 0.7122 0.8119 0.045 Uiso 1 1 calc R U . . .
C32 C 0.9440(3) 0.6402(2) 0.8790(2) 0.0419(11) Uani 1 1 d . . . . .
H32 H 1.0082 0.6488 0.8944 0.050 Uiso 1 1 calc R U . . .
C33 C 0.8981(3) 0.5901(2) 0.9047(2) 0.0451(12) Uani 1 1 d . . . . .
H33 H 0.9294 0.5635 0.9380 0.054 Uiso 1 1 calc R U . . .
C34 C 0.8043(3) 0.5791(2) 0.8807(2) 0.0389(11) Uani 1 1 d . . . . .
H34 H 0.7723 0.5438 0.8976 0.047 Uiso 1 1 calc R U . . .
C35 C 0.6985(3) 0.67824(18) 0.6983(2) 0.0308(10) Uani 1 1 d . . . . .
C36 C 0.7191(3) 0.69537(19) 0.6331(2) 0.0366(11) Uani 1 1 d . . . . .
H36 H 0.7644 0.7273 0.6261 0.044 Uiso 1 1 calc R U . . .
C37 C 0.6724(3) 0.6653(2) 0.5788(2) 0.0399(11) Uani 1 1 d . . . . .
H37 H 0.6879 0.6750 0.5337 0.048 Uiso 1 1 calc R U . . .
C38 C 0.6034(3) 0.6211(2) 0.5887(2) 0.0384(11) Uani 1 1 d . . . . .
H38 H 0.5703 0.6006 0.5511 0.046 Uiso 1 1 calc R U . . .
C39 C 0.5836(3) 0.60729(17) 0.6557(2) 0.0290(9) Uani 1 1 d . . . . .
C40 C 0.5027(3) 0.56797(18) 0.6733(2) 0.0342(10) Uani 1 1 d . . . . .
C41 C 0.4456(3) 0.53498(19) 0.6256(2) 0.0391(11) Uani 1 1 d . . . . .
H41 H 0.4608 0.5336 0.5793 0.047 Uiso 1 1 calc R U . . .
C42 C 0.3666(3) 0.5041(2) 0.6459(3) 0.0431(12) Uani 1 1 d . . . . .
H42 H 0.3257 0.4821 0.6135 0.052 Uiso 1 1 calc R U . . .
C43 C 0.3475(3) 0.5054(2) 0.7133(3) 0.0432(12) Uani 1 1 d . . . . .
H43 H 0.2937 0.4842 0.7286 0.052 Uiso 1 1 calc R U . . .
C44 C 0.4084(3) 0.53843(19) 0.7581(2) 0.0394(11) Uani 1 1 d . . . . .
H44 H 0.3952 0.5390 0.8049 0.047 Uiso 1 1 calc R U . . .
C45 C 0.6649(3) 0.74083(18) 0.8005(2) 0.0305(9) Uani 1 1 d . . . . .
C46 C 0.6515(3) 0.8050(2) 0.8054(2) 0.0427(12) Uani 1 1 d . . . . .
H46 H 0.6880 0.8337 0.7811 0.051 Uiso 1 1 calc R U . . .
C47 C 0.5827(3) 0.8257(2) 0.8473(3) 0.0541(14) Uani 1 1 d . . . . .
H47 H 0.5697 0.8693 0.8507 0.065 Uiso 1 1 calc R U . . .
C48 C 0.5330(3) 0.7830(2) 0.8842(3) 0.0468(12) Uani 1 1 d . . . . .
H48 H 0.4885 0.7970 0.9150 0.056 Uiso 1 1 calc R U . . .
C49 C 0.5490(3) 0.7203(2) 0.8756(2) 0.0373(11) Uani 1 1 d . . . . .
C50 C 0.5039(3) 0.6689(2) 0.9125(2) 0.0356(10) Uani 1 1 d . . . . .
C51 C 0.4492(3) 0.6797(2) 0.9680(2) 0.0452(12) Uani 1 1 d . . . . .
H51 H 0.4388 0.7213 0.9832 0.054 Uiso 1 1 calc R U . . .
C52 C 0.4110(3) 0.6296(3) 1.0000(2) 0.0540(14) Uani 1 1 d . . . . .
H52 H 0.3724 0.6361 1.0371 0.065 Uiso 1 1 calc R U . . .
C53 C 0.4289(3) 0.5701(2) 0.9780(2) 0.0455(12) Uani 1 1 d . . . . .
H53 H 0.4025 0.5348 0.9993 0.055 Uiso 1 1 calc R U . . .
C54 C 0.4854(3) 0.5622(2) 0.9250(2) 0.0415(11) Uani 1 1 d . . . . .
H54 H 0.4991 0.5206 0.9112 0.050 Uiso 1 1 calc R U . . .
C55 C 0.6295(3) 0.4519(2) 0.8071(2) 0.0336(10) Uani 1 1 d . . . . .
C56 C 0.6277(4) 0.3834(2) 0.7984(3) 0.0514(13) Uani 1 1 d . . . . .
H56A H 0.6288 0.3731 0.7498 0.077 Uiso 1 1 calc R U . . .
H56B H 0.5696 0.3665 0.8159 0.077 Uiso 1 1 calc R U . . .
H56C H 0.6834 0.3650 0.8237 0.077 Uiso 1 1 calc R U . . .


_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 N4 2.095(3) . ?
Co1 N2 2.097(3) . ?
Co1 N6 2.098(4) . ?
Co1 N3 2.135(4) . ?
Co1 N1 2.172(3) . ?
Co1 N5 2.217(3) . ?
Co2 N8 2.102(3) . ?
Co2 N10 2.112(3) . ?
Co2 N11 2.114(3) . ?
Co2 N12 2.118(4) . ?
Co2 N7 2.130(3) . ?
Co2 N9 2.229(3) . ?
Cl1 O3 1.402(4) . ?
Cl1 O4 1.410(4) . ?
Cl1 O6 1.440(4) . ?
Cl1 O5 1.441(3) . ?
Cl2 O9A 1.359(12) . ?
Cl2 O8A 1.370(10) . ?
Cl2 O7A 1.403(12) . ?
Cl2 O9 1.419(6) . ?
Cl2 O10 1.418(3) . ?
Cl2 O8 1.428(6) . ?
Cl2 O7 1.467(8) . ?
Cl3 O13 1.410(4) . ?
Cl3 O14 1.425(4) . ?
Cl3 O12 1.433(4) . ?
Cl3 O11 1.479(4) . ?
Cl4 O16A 1.27(2) . ?
Cl4 O15 1.390(5) . ?
Cl4 O17 1.414(5) . ?
Cl4 O16 1.433(5) . ?
Cl4 O18 1.435(4) . ?
Cl4 O15A 1.46(2) . ?
Cl4 O17A 1.47(2) . ?
O1 C1 1.394(5) . ?
O1 H1 0.852(19) . ?
O2 C29 1.404(4) . ?
O2 H2 0.807(19) . ?
O19 H1O 0.85(2) . ?
O19 H2O 0.87(9) . ?
N1 C2 1.344(5) . ?
N1 C6 1.349(5) . ?
N2 C7 1.331(5) . ?
N2 C11 1.359(5) . ?
N3 C16 1.336(6) . ?
N3 C12 1.353(5) . ?
N4 C17 1.343(5) . ?
N4 C21 1.352(5) . ?
N5 C26 1.332(5) . ?
N5 C22 1.342(5) . ?
N6 C27 1.122(5) . ?
N7 C34 1.339(5) . ?
N7 C30 1.356(5) . ?
N8 C35 1.343(5) . ?
N8 C39 1.348(5) . ?
N9 C44 1.337(5) . ?
N9 C40 1.356(5) . ?
N10 C45 1.335(5) . ?
N10 C49 1.349(5) . ?
N11 C54 1.342(5) . ?
N11 C50 1.349(5) . ?
N12 C55 1.125(5) . ?
C1 C2 1.532(6) . ?
C1 C17 1.535(6) . ?
C1 C7 1.537(6) . ?
C2 C3 1.394(5) . ?
C3 C4 1.381(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.356(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.387(6) . ?
C8 C9 1.389(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.362(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.384(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.453(6) . ?
C12 C13 1.403(6) . ?
C13 C14 1.383(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.373(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.373(6) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.394(6) . ?
C18 C19 1.376(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.380(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.378(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.476(6) . ?
C22 C23 1.409(5) . ?
C23 C24 1.375(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.375(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.392(6) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.475(6) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C30 1.534(6) . ?
C29 C35 1.536(6) . ?
C29 C45 1.539(5) . ?
C30 C31 1.392(5) . ?
C31 C32 1.369(6) . ?
C31 H31 0.9500 . ?
C32 C33 1.364(6) . ?
C32 H32 0.9500 . ?
C33 C34 1.390(6) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C35 C36 1.383(6) . ?
C36 C37 1.369(6) . ?
C36 H36 0.9500 . ?
C37 C38 1.377(6) . ?
C37 H37 0.9500 . ?
C38 C39 1.396(6) . ?
C38 H38 0.9500 . ?
C39 C40 1.476(5) . ?
C40 C41 1.380(6) . ?
C41 C42 1.377(6) . ?
C41 H41 0.9500 . ?
C42 C43 1.369(6) . ?
C42 H42 0.9500 . ?
C43 C44 1.377(6) . ?
C43 H43 0.9500 . ?
C44 H44 0.9500 . ?
C45 C46 1.384(5) . ?
C46 C47 1.389(6) . ?
C46 H46 0.9500 . ?
C47 C48 1.385(6) . ?
C47 H47 0.9500 . ?
C48 C49 1.367(6) . ?
C48 H48 0.9500 . ?
C49 C50 1.482(6) . ?
C50 C51 1.399(6) . ?
C51 C52 1.369(7) . ?
C51 H51 0.9500 . ?
C52 C53 1.369(7) . ?
C52 H52 0.9500 . ?
C53 C54 1.366(6) . ?
C53 H53 0.9500 . ?
C54 H54 0.9500 . ?
C55 C56 1.469(6) . ?
C56 H56A 0.9800 . ?
C56 H56B 0.9800 . ?
C56 H56C 0.9800 . ?

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
N4 Co1 N2 82.91(13) . . ?
N4 Co1 N6 111.27(14) . . ?
N2 Co1 N6 162.20(13) . . ?
N4 Co1 N3 146.36(13) . . ?
N2 Co1 N3 76.11(14) . . ?
N6 Co1 N3 95.28(15) . . ?
N4 Co1 N1 86.26(13) . . ?
N2 Co1 N1 81.76(12) . . ?
N6 Co1 N1 88.30(13) . . ?
N3 Co1 N1 115.80(13) . . ?
N4 Co1 N5 73.82(13) . . ?
N2 Co1 N5 114.29(12) . . ?
N6 Co1 N5 80.98(13) . . ?
N3 Co1 N5 91.12(13) . . ?
N1 Co1 N5 151.91(12) . . ?
N8 Co2 N10 84.01(13) . . ?
N8 Co2 N11 146.74(13) . . ?
N10 Co2 N11 76.17(13) . . ?
N8 Co2 N12 108.36(13) . . ?
N10 Co2 N12 162.90(14) . . ?
N11 Co2 N12 97.40(13) . . ?
N8 Co2 N7 87.46(13) . . ?
N10 Co2 N7 79.37(12) . . ?
N11 Co2 N7 114.17(13) . . ?
N12 Co2 N7 89.20(12) . . ?
N8 Co2 N9 74.02(12) . . ?
N10 Co2 N9 116.11(12) . . ?
N11 Co2 N9 90.95(13) . . ?
N12 Co2 N9 79.40(12) . . ?
N7 Co2 N9 153.67(12) . . ?
O3 Cl1 O4 110.9(3) . . ?
O3 Cl1 O6 108.8(2) . . ?
O4 Cl1 O6 111.6(3) . . ?
O3 Cl1 O5 110.1(3) . . ?
O4 Cl1 O5 107.5(2) . . ?
O6 Cl1 O5 107.9(2) . . ?
O9A Cl2 O8A 116.6(8) . . ?
O9A Cl2 O7A 113.5(8) . . ?
O8A Cl2 O7A 109.7(7) . . ?
O9A Cl2 O10 104.5(6) . . ?
O8A Cl2 O10 103.2(5) . . ?
O7A Cl2 O10 108.4(7) . . ?
O9 Cl2 O10 112.5(4) . . ?
O9 Cl2 O8 106.9(5) . . ?
O10 Cl2 O8 116.9(3) . . ?
O9 Cl2 O7 102.9(6) . . ?
O10 Cl2 O7 108.8(4) . . ?
O8 Cl2 O7 107.8(5) . . ?
O13 Cl3 O14 110.7(3) . . ?
O13 Cl3 O12 111.4(3) . . ?
O14 Cl3 O12 110.3(2) . . ?
O13 Cl3 O11 108.8(3) . . ?
O14 Cl3 O11 108.9(2) . . ?
O12 Cl3 O11 106.5(2) . . ?
O15 Cl4 O17 109.9(4) . . ?
O15 Cl4 O16 109.9(3) . . ?
O17 Cl4 O16 108.6(3) . . ?
O16A Cl4 O18 106.0(13) . . ?
O15 Cl4 O18 109.4(3) . . ?
O17 Cl4 O18 108.8(3) . . ?
O16 Cl4 O18 110.2(3) . . ?
O16A Cl4 O15A 114.4(15) . . ?
O18 Cl4 O15A 106.2(13) . . ?
O16A Cl4 O17A 115.8(15) . . ?
O18 Cl4 O17A 113.7(10) . . ?
O15A Cl4 O17A 100.5(13) . . ?
C1 O1 H1 109.5 . . ?
C29 O2 H2 109.5 . . ?
H1O O19 H2O 102(7) . . ?
C2 N1 C6 118.2(4) . . ?
C2 N1 Co1 120.2(3) . . ?
C6 N1 Co1 121.1(3) . . ?
C7 N2 C11 120.9(4) . . ?
C7 N2 Co1 122.6(3) . . ?
C11 N2 Co1 116.5(3) . . ?
C16 N3 C12 118.2(4) . . ?
C16 N3 Co1 126.9(3) . . ?
C12 N3 Co1 114.6(3) . . ?
C17 N4 C21 119.6(4) . . ?
C17 N4 Co1 120.8(3) . . ?
C21 N4 Co1 119.1(3) . . ?
C26 N5 C22 117.8(3) . . ?
C26 N5 Co1 127.7(3) . . ?
C22 N5 Co1 114.3(3) . . ?
C27 N6 Co1 177.2(4) . . ?
C34 N7 C30 118.4(3) . . ?
C34 N7 Co2 121.1(3) . . ?
C30 N7 Co2 120.1(3) . . ?
C35 N8 C39 119.4(3) . . ?
C35 N8 Co2 122.1(3) . . ?
C39 N8 Co2 118.4(3) . . ?
C44 N9 C40 116.7(4) . . ?
C44 N9 Co2 127.7(3) . . ?
C40 N9 Co2 113.4(3) . . ?
C45 N10 C49 119.7(3) . . ?
C45 N10 Co2 122.8(2) . . ?
C49 N10 Co2 117.2(3) . . ?
C54 N11 C50 117.6(4) . . ?
C54 N11 Co2 126.2(3) . . ?
C50 N11 Co2 116.1(3) . . ?
C55 N12 Co2 168.4(3) . . ?
O1 C1 C2 106.7(3) . . ?
O1 C1 C17 110.4(3) . . ?
C2 C1 C17 110.8(3) . . ?
O1 C1 C7 110.8(3) . . ?
C2 C1 C7 107.7(3) . . ?
C17 C1 C7 110.3(3) . . ?
N1 C2 C3 122.1(4) . . ?
N1 C2 C1 116.9(3) . . ?
C3 C2 C1 121.0(4) . . ?
C4 C3 C2 118.3(4) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C5 C4 C3 120.0(4) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 119.1(4) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
N1 C6 C5 122.2(5) . . ?
N1 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
N2 C7 C8 121.3(4) . . ?
N2 C7 C1 116.5(3) . . ?
C8 C7 C1 121.9(4) . . ?
C9 C8 C7 117.5(5) . . ?
C9 C8 H8 121.3 . . ?
C7 C8 H8 121.3 . . ?
C10 C9 C8 121.1(4) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C9 C10 C11 118.9(4) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 H10 120.6 . . ?
N2 C11 C10 120.0(4) . . ?
N2 C11 C12 114.3(4) . . ?
C10 C11 C12 125.5(4) . . ?
N3 C12 C13 120.6(5) . . ?
N3 C12 C11 116.1(4) . . ?
C13 C12 C11 123.2(4) . . ?
C14 C13 C12 119.6(5) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C15 C14 C13 119.1(5) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 118.5(5) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
N3 C16 C15 123.9(5) . . ?
N3 C16 H16 118.0 . . ?
C15 C16 H16 118.0 . . ?
N4 C17 C18 120.9(4) . . ?
N4 C17 C1 117.3(4) . . ?
C18 C17 C1 121.8(4) . . ?
C19 C18 C17 119.0(4) . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C18 C19 C20 119.7(4) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C21 C20 C19 118.9(4) . . ?
C21 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
N4 C21 C20 121.4(4) . . ?
N4 C21 C22 112.7(4) . . ?
C20 C21 C22 125.7(4) . . ?
N5 C22 C23 122.4(4) . . ?
N5 C22 C21 116.1(3) . . ?
C23 C22 C21 121.4(4) . . ?
C24 C23 C22 118.2(4) . . ?
C24 C23 H23 120.9 . . ?
C22 C23 H23 120.9 . . ?
C23 C24 C25 119.9(4) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 C26 118.1(4) . . ?
C24 C25 H25 121.0 . . ?
C26 C25 H25 121.0 . . ?
N5 C26 C25 123.6(4) . . ?
N5 C26 H26 118.2 . . ?
C25 C26 H26 118.2 . . ?
N6 C27 C28 179.6(5) . . ?
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 . . ?
O2 C29 C30 109.6(3) . . ?
O2 C29 C35 106.6(3) . . ?
C30 C29 C35 113.2(3) . . ?
O2 C29 C45 110.8(3) . . ?
C30 C29 C45 109.0(3) . . ?
C35 C29 C45 107.7(3) . . ?
N7 C30 C31 120.8(4) . . ?
N7 C30 C29 117.7(3) . . ?
C31 C30 C29 121.5(4) . . ?
C32 C31 C30 119.6(4) . . ?
C32 C31 H31 120.2 . . ?
C30 C31 H31 120.2 . . ?
C33 C32 C31 120.1(4) . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C32 C33 C34 118.1(4) . . ?
C32 C33 H33 121.0 . . ?
C34 C33 H33 121.0 . . ?
N7 C34 C33 123.0(4) . . ?
N7 C34 H34 118.5 . . ?
C33 C34 H34 118.5 . . ?
N8 C35 C36 121.8(4) . . ?
N8 C35 C29 116.3(3) . . ?
C36 C35 C29 121.8(4) . . ?
C37 C36 C35 118.5(4) . . ?
C37 C36 H36 120.8 . . ?
C35 C36 H36 120.8 . . ?
C36 C37 C38 120.8(4) . . ?
C36 C37 H37 119.6 . . ?
C38 C37 H37 119.6 . . ?
C37 C38 C39 118.1(4) . . ?
C37 C38 H38 121.0 . . ?
C39 C38 H38 121.0 . . ?
N8 C39 C38 121.2(4) . . ?
N8 C39 C40 115.1(4) . . ?
C38 C39 C40 123.5(4) . . ?
N9 C40 C41 122.2(4) . . ?
N9 C40 C39 114.2(4) . . ?
C41 C40 C39 123.5(4) . . ?
C40 C41 C42 119.3(4) . . ?
C40 C41 H41 120.4 . . ?
C42 C41 H41 120.4 . . ?
C43 C42 C41 119.4(4) . . ?
C43 C42 H42 120.3 . . ?
C41 C42 H42 120.3 . . ?
C42 C43 C44 118.1(4) . . ?
C42 C43 H43 120.9 . . ?
C44 C43 H43 120.9 . . ?
N9 C44 C43 124.3(4) . . ?
N9 C44 H44 117.8 . . ?
C43 C44 H44 117.8 . . ?
N10 C45 C46 122.2(4) . . ?
N10 C45 C29 114.4(3) . . ?
C46 C45 C29 123.3(4) . . ?
C45 C46 C47 117.4(4) . . ?
C45 C46 H46 121.3 . . ?
C47 C46 H46 121.3 . . ?
C48 C47 C46 120.2(4) . . ?
C48 C47 H47 119.9 . . ?
C46 C47 H47 119.9 . . ?
C49 C48 C47 118.8(4) . . ?
C49 C48 H48 120.6 . . ?
C47 C48 H48 120.6 . . ?
N10 C49 C48 121.3(4) . . ?
N10 C49 C50 113.2(4) . . ?
C48 C49 C50 125.5(4) . . ?
N11 C50 C51 121.4(4) . . ?
N11 C50 C49 115.9(3) . . ?
C51 C50 C49 122.6(4) . . ?
C52 C51 C50 119.2(4) . . ?
C52 C51 H51 120.4 . . ?
C50 C51 H51 120.4 . . ?
C51 C52 C53 119.2(4) . . ?
C51 C52 H52 120.4 . . ?
C53 C52 H52 120.4 . . ?
C54 C53 C52 119.1(5) . . ?
C54 C53 H53 120.5 . . ?
C52 C53 H53 120.5 . . ?
N11 C54 C53 123.4(4) . . ?
N11 C54 H54 118.3 . . ?
C53 C54 H54 118.3 . . ?
N12 C55 C56 179.0(5) . . ?
C55 C56 H56A 109.5 . . ?
C55 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
C55 C56 H56C 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?

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
C6 N1 C2 C3 1.0(6) . . . . ?
Co1 N1 C2 C3 -171.0(3) . . . . ?
C6 N1 C2 C1 179.7(3) . . . . ?
Co1 N1 C2 C1 7.7(5) . . . . ?
O1 C1 C2 N1 174.6(3) . . . . ?
C17 C1 C2 N1 54.4(5) . . . . ?
C7 C1 C2 N1 -66.4(4) . . . . ?
O1 C1 C2 C3 -6.7(5) . . . . ?
C17 C1 C2 C3 -126.9(4) . . . . ?
C7 C1 C2 C3 112.4(4) . . . . ?
N1 C2 C3 C4 1.0(6) . . . . ?
C1 C2 C3 C4 -177.7(4) . . . . ?
C2 C3 C4 C5 -2.6(6) . . . . ?
C3 C4 C5 C6 2.1(6) . . . . ?
C2 N1 C6 C5 -1.5(6) . . . . ?
Co1 N1 C6 C5 170.5(3) . . . . ?
C4 C5 C6 N1 -0.1(6) . . . . ?
C11 N2 C7 C8 2.3(6) . . . . ?
Co1 N2 C7 C8 -176.0(3) . . . . ?
C11 N2 C7 C1 -173.0(3) . . . . ?
Co1 N2 C7 C1 8.8(5) . . . . ?
O1 C1 C7 N2 174.0(3) . . . . ?
C2 C1 C7 N2 57.6(4) . . . . ?
C17 C1 C7 N2 -63.4(5) . . . . ?
O1 C1 C7 C8 -1.2(5) . . . . ?
C2 C1 C7 C8 -117.6(4) . . . . ?
C17 C1 C7 C8 121.4(4) . . . . ?
N2 C7 C8 C9 3.0(6) . . . . ?
C1 C7 C8 C9 178.0(4) . . . . ?
C7 C8 C9 C10 -4.7(6) . . . . ?
C8 C9 C10 C11 1.2(7) . . . . ?
C7 N2 C11 C10 -5.9(5) . . . . ?
Co1 N2 C11 C10 172.5(3) . . . . ?
C7 N2 C11 C12 169.3(3) . . . . ?
Co1 N2 C11 C12 -12.3(4) . . . . ?
C9 C10 C11 N2 4.1(6) . . . . ?
C9 C10 C11 C12 -170.6(4) . . . . ?
C16 N3 C12 C13 2.1(6) . . . . ?
Co1 N3 C12 C13 -173.0(3) . . . . ?
C16 N3 C12 C11 -174.7(3) . . . . ?
Co1 N3 C12 C11 10.2(4) . . . . ?
N2 C11 C12 N3 1.1(5) . . . . ?
C10 C11 C12 N3 176.0(4) . . . . ?
N2 C11 C12 C13 -175.5(3) . . . . ?
C10 C11 C12 C13 -0.6(6) . . . . ?
N3 C12 C13 C14 -1.0(6) . . . . ?
C11 C12 C13 C14 175.5(4) . . . . ?
C12 C13 C14 C15 -0.9(6) . . . . ?
C13 C14 C15 C16 1.5(7) . . . . ?
C12 N3 C16 C15 -1.4(6) . . . . ?
Co1 N3 C16 C15 173.0(3) . . . . ?
C14 C15 C16 N3 -0.4(7) . . . . ?
C21 N4 C17 C18 5.5(5) . . . . ?
Co1 N4 C17 C18 -166.3(3) . . . . ?
C21 N4 C17 C1 -172.0(3) . . . . ?
Co1 N4 C17 C1 16.1(4) . . . . ?
O1 C1 C17 N4 171.7(3) . . . . ?
C2 C1 C17 N4 -70.3(4) . . . . ?
C7 C1 C17 N4 48.9(5) . . . . ?
O1 C1 C17 C18 -5.8(5) . . . . ?
C2 C1 C17 C18 112.2(4) . . . . ?
C7 C1 C17 C18 -128.6(4) . . . . ?
N4 C17 C18 C19 0.0(6) . . . . ?
C1 C17 C18 C19 177.5(4) . . . . ?
C17 C18 C19 C20 -3.8(6) . . . . ?
C18 C19 C20 C21 2.1(6) . . . . ?
C17 N4 C21 C20 -7.4(5) . . . . ?
Co1 N4 C21 C20 164.6(3) . . . . ?
C17 N4 C21 C22 168.5(3) . . . . ?
Co1 N4 C21 C22 -19.5(4) . . . . ?
C19 C20 C21 N4 3.6(6) . . . . ?
C19 C20 C21 C22 -171.8(4) . . . . ?
C26 N5 C22 C23 -1.4(5) . . . . ?
Co1 N5 C22 C23 -175.9(3) . . . . ?
C26 N5 C22 C21 -176.2(3) . . . . ?
Co1 N5 C22 C21 9.3(4) . . . . ?
N4 C21 C22 N5 5.7(5) . . . . ?
C20 C21 C22 N5 -178.6(4) . . . . ?
N4 C21 C22 C23 -169.2(3) . . . . ?
C20 C21 C22 C23 6.5(6) . . . . ?
N5 C22 C23 C24 0.6(6) . . . . ?
C21 C22 C23 C24 175.2(4) . . . . ?
C22 C23 C24 C25 0.4(6) . . . . ?
C23 C24 C25 C26 -0.6(6) . . . . ?
C22 N5 C26 C25 1.2(6) . . . . ?
Co1 N5 C26 C25 174.9(3) . . . . ?
C24 C25 C26 N5 -0.2(6) . . . . ?
C34 N7 C30 C31 2.0(5) . . . . ?
Co2 N7 C30 C31 175.5(3) . . . . ?
C34 N7 C30 C29 -175.4(3) . . . . ?
Co2 N7 C30 C29 -1.9(4) . . . . ?
O2 C29 C30 N7 -176.0(3) . . . . ?
C35 C29 C30 N7 -57.1(4) . . . . ?
C45 C29 C30 N7 62.6(4) . . . . ?
O2 C29 C30 C31 6.7(5) . . . . ?
C35 C29 C30 C31 125.5(4) . . . . ?
C45 C29 C30 C31 -114.7(4) . . . . ?
N7 C30 C31 C32 -3.2(6) . . . . ?
C29 C30 C31 C32 174.0(4) . . . . ?
C30 C31 C32 C33 2.1(6) . . . . ?
C31 C32 C33 C34 0.1(6) . . . . ?
C30 N7 C34 C33 0.3(6) . . . . ?
Co2 N7 C34 C33 -173.1(3) . . . . ?
C32 C33 C34 N7 -1.3(6) . . . . ?
C39 N8 C35 C36 -3.8(5) . . . . ?
Co2 N8 C35 C36 175.7(3) . . . . ?
C39 N8 C35 C29 173.5(3) . . . . ?
Co2 N8 C35 C29 -7.0(4) . . . . ?
O2 C29 C35 N8 -176.8(3) . . . . ?
C30 C29 C35 N8 62.6(4) . . . . ?
C45 C29 C35 N8 -58.0(4) . . . . ?
O2 C29 C35 C36 0.5(5) . . . . ?
C30 C29 C35 C36 -120.1(4) . . . . ?
C45 C29 C35 C36 119.4(4) . . . . ?
N8 C35 C36 C37 -0.7(6) . . . . ?
C29 C35 C36 C37 -177.9(4) . . . . ?
C35 C36 C37 C38 3.1(6) . . . . ?
C36 C37 C38 C39 -1.0(6) . . . . ?
C35 N8 C39 C38 6.0(5) . . . . ?
Co2 N8 C39 C38 -173.5(3) . . . . ?
C35 N8 C39 C40 -169.0(3) . . . . ?
Co2 N8 C39 C40 11.4(4) . . . . ?
C37 C38 C39 N8 -3.6(6) . . . . ?
C37 C38 C39 C40 171.0(4) . . . . ?
C44 N9 C40 C41 -0.8(6) . . . . ?
Co2 N9 C40 C41 163.7(3) . . . . ?
C44 N9 C40 C39 175.5(3) . . . . ?
Co2 N9 C40 C39 -20.0(4) . . . . ?
N8 C39 C40 N9 6.7(5) . . . . ?
C38 C39 C40 N9 -168.2(4) . . . . ?
N8 C39 C40 C41 -177.1(4) . . . . ?
C38 C39 C40 C41 8.0(6) . . . . ?
N9 C40 C41 C42 1.8(6) . . . . ?
C39 C40 C41 C42 -174.2(4) . . . . ?
C40 C41 C42 C43 -1.6(6) . . . . ?
C41 C42 C43 C44 0.6(6) . . . . ?
C40 N9 C44 C43 -0.3(6) . . . . ?
Co2 N9 C44 C43 -162.3(3) . . . . ?
C42 C43 C44 N9 0.5(6) . . . . ?
C49 N10 C45 C46 -7.4(6) . . . . ?
Co2 N10 C45 C46 166.0(3) . . . . ?
C49 N10 C45 C29 169.7(4) . . . . ?
Co2 N10 C45 C29 -17.0(5) . . . . ?
O2 C29 C45 N10 -172.1(3) . . . . ?
C30 C29 C45 N10 -51.5(4) . . . . ?
C35 C29 C45 N10 71.7(4) . . . . ?
O2 C29 C45 C46 4.9(6) . . . . ?
C30 C29 C45 C46 125.6(4) . . . . ?
C35 C29 C45 C46 -111.3(4) . . . . ?
N10 C45 C46 C47 3.2(6) . . . . ?
C29 C45 C46 C47 -173.6(4) . . . . ?
C45 C46 C47 C48 2.4(7) . . . . ?
C46 C47 C48 C49 -3.7(7) . . . . ?
C45 N10 C49 C48 6.0(6) . . . . ?
Co2 N10 C49 C48 -167.7(3) . . . . ?
C45 N10 C49 C50 -172.8(4) . . . . ?
Co2 N10 C49 C50 13.5(5) . . . . ?
C47 C48 C49 N10 -0.5(7) . . . . ?
C47 C48 C49 C50 178.2(4) . . . . ?
C54 N11 C50 C51 1.0(6) . . . . ?
Co2 N11 C50 C51 -178.7(3) . . . . ?
C54 N11 C50 C49 177.9(4) . . . . ?
Co2 N11 C50 C49 -1.8(5) . . . . ?
N10 C49 C50 N11 -7.6(5) . . . . ?
C48 C49 C50 N11 173.7(4) . . . . ?
N10 C49 C50 C51 169.3(4) . . . . ?
C48 C49 C50 C51 -9.4(7) . . . . ?
N11 C50 C51 C52 -2.4(6) . . . . ?
C49 C50 C51 C52 -179.1(4) . . . . ?
C50 C51 C52 C53 1.5(7) . . . . ?
C51 C52 C53 C54 0.6(7) . . . . ?
C50 N11 C54 C53 1.3(6) . . . . ?
Co2 N11 C54 C53 -179.1(3) . . . . ?
C52 C53 C54 N11 -2.1(7) . . . . ?

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
O1 H1 O19 0.85 1.86 2.707(5) 178.1 .
O2 H2 O11 0.81 2.06 2.859(5) 168.3 .
O19 H2O O9 0.87(9) 2.26(11) 2.907(11) 131(12) 4_576
O19 H2O O7A 0.87(9) 2.15(12) 2.768(14) 128(13) 4_576
O19 H1O O6 0.85(2) 2.36(7) 3.152(6) 156(15) .

_refine_diff_density_max         1.113
_refine_diff_density_min         -0.628
_refine_diff_density_rms         0.088

####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 1470088'
_audit_update_record             
;
2016-03-22 deposited with the CCDC.
2016-05-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H19 Br Cl N5 Ni O5'
_chemical_formula_weight         655.53

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.4513(3)
_cell_length_b                   10.2182(3)
_cell_length_c                   20.2607(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.8620(10)
_cell_angle_gamma                90
_cell_volume                     2522.72(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    18091
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_F_000             1320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.508
_shelx_estimated_absorpt_T_min   0.562
_shelx_estimated_absorpt_T_max   0.634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.515
_exptl_absorpt_correction_T_max  0.604
_exptl_absorpt_process_details   'Sortav (Blessing, 1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'profile from ω scans'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            21051
_diffrn_reflns_av_unetI/netI     0.1040
_diffrn_reflns_av_R_equivalents  0.1351
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.921
_diffrn_reflns_theta_max         27.431
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5720
_reflns_number_gt                3894
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997
;
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ddifmap?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5720
_refine_ls_number_parameters     354
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1098
_refine_ls_R_factor_gt           0.0678
_refine_ls_wR_factor_ref         0.2018
_refine_ls_wR_factor_gt          0.1787
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.137
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.24730(6) 0.14142(6) 0.60618(3) 0.0319(2) Uani 1 1 d . . . . .
Ni1 Ni 0.24762(6) 0.38620(6) 0.58314(3) 0.0166(2) Uani 1 1 d . . . . .
Cl1 Cl 0.80503(13) 0.56917(14) 0.85764(8) 0.0282(4) Uani 1 1 d . . . . .
O1 O 0.2820(4) 0.7044(3) 0.74113(19) 0.0239(9) Uani 1 1 d D . . . .
H1 H 0.282(6) 0.6754(9) 0.7790(11) 0.036 Uiso 1 1 calc DR U . . .
O2 O 0.7884(4) 0.4853(4) 0.7994(2) 0.0390(12) Uani 1 1 d . . . . .
O3 O 0.7543(5) 0.6934(5) 0.8388(3) 0.0571(16) Uani 1 1 d . . . . .
O4 O 0.7562(4) 0.5116(4) 0.9085(2) 0.0341(11) Uani 1 1 d . . . . .
O5 O 0.9208(4) 0.5868(5) 0.8831(3) 0.0474(13) Uani 1 1 d . . . . .
N1 N 0.3746(4) 0.4082(4) 0.6690(2) 0.0192(10) Uani 1 1 d . . . . .
N2 N 0.1383(4) 0.4424(4) 0.6385(2) 0.0182(10) Uani 1 1 d . . . . .
N3 N 0.0858(4) 0.3363(5) 0.5195(2) 0.0247(11) Uani 1 1 d . . . . .
N4 N 0.2844(4) 0.5796(4) 0.5765(2) 0.0202(10) Uani 1 1 d . . . . .
N5 N 0.3225(4) 0.3840(4) 0.5000(2) 0.0201(10) Uani 1 1 d . . . . .
C1 C 0.2730(5) 0.6005(5) 0.6951(3) 0.0187(12) Uani 1 1 d . . . . .
C2 C 0.3682(5) 0.5035(5) 0.7138(3) 0.0198(12) Uani 1 1 d . . . . .
C3 C 0.4464(5) 0.5182(6) 0.7722(3) 0.0249(13) Uani 1 1 d . . . . .
H3 H 0.4385 0.5838 0.8040 0.030 Uiso 1 1 calc R U . . .
C4 C 0.5366(5) 0.4363(7) 0.7839(3) 0.0331(15) Uani 1 1 d . . . . .
H4 H 0.5913 0.4444 0.8240 0.040 Uiso 1 1 calc R U . . .
C5 C 0.5461(5) 0.3412(6) 0.7358(3) 0.0293(14) Uani 1 1 d . . . . .
H5 H 0.6085 0.2856 0.7419 0.035 Uiso 1 1 calc R U . . .
C6 C 0.4645(5) 0.3298(5) 0.6802(3) 0.0217(13) Uani 1 1 d . . . . .
H6 H 0.4706 0.2644 0.6479 0.026 Uiso 1 1 calc R U . . .
C7 C 0.1622(5) 0.5316(5) 0.6876(3) 0.0202(12) Uani 1 1 d . . . . .
C8 C 0.0883(5) 0.5595(6) 0.7279(3) 0.0273(14) Uani 1 1 d . . . . .
H8 H 0.1059 0.6228 0.7628 0.033 Uiso 1 1 calc R U . . .
C9 C -0.0106(6) 0.4955(6) 0.7175(3) 0.0339(16) Uani 1 1 d . . . . .
H9 H -0.0601 0.5106 0.7467 0.041 Uiso 1 1 calc R U . . .
C10 C -0.0383(6) 0.4080(6) 0.6637(3) 0.0310(15) Uani 1 1 d . . . . .
H10 H -0.1077 0.3658 0.6540 0.037 Uiso 1 1 calc R U . . .
C11 C 0.0401(5) 0.3849(5) 0.6247(3) 0.0204(12) Uani 1 1 d . . . . .
C12 C 0.0157(5) 0.3100(5) 0.5607(3) 0.0235(13) Uani 1 1 d . . . . .
C13 C -0.0688(5) 0.2208(6) 0.5459(3) 0.0277(14) Uani 1 1 d . . . . .
H13 H -0.1155 0.2051 0.5767 0.033 Uiso 1 1 calc R U . . .
C14 C -0.0841(6) 0.1547(7) 0.4852(4) 0.0395(18) Uani 1 1 d . . . . .
H14 H -0.1381 0.0880 0.4747 0.047 Uiso 1 1 calc R U . . .
C15 C -0.0191(6) 0.1881(8) 0.4399(3) 0.0431(18) Uani 1 1 d . . . . .
H15 H -0.0325 0.1506 0.3961 0.052 Uiso 1 1 calc R U . . .
C16 C 0.0652(6) 0.2762(7) 0.4591(3) 0.0337(15) Uani 1 1 d . . . . .
H16 H 0.1110 0.2956 0.4282 0.040 Uiso 1 1 calc R U . . .
C17 C 0.2913(5) 0.6620(5) 0.6287(3) 0.0184(12) Uani 1 1 d . . . . .
C18 C 0.3282(5) 0.7894(6) 0.6253(3) 0.0288(14) Uani 1 1 d . . . . .
H18 H 0.3295 0.8483 0.6617 0.035 Uiso 1 1 calc R U . . .
C19 C 0.3632(6) 0.8292(6) 0.5680(3) 0.0298(14) Uani 1 1 d . . . . .
H19 H 0.3869 0.9168 0.5643 0.036 Uiso 1 1 calc R U . . .
C20 C 0.3639(5) 0.7417(5) 0.5160(3) 0.0261(14) Uani 1 1 d . . . . .
H20 H 0.3910 0.7668 0.4773 0.031 Uiso 1 1 calc R U . . .
C21 C 0.3240(5) 0.6164(5) 0.5216(3) 0.0212(13) Uani 1 1 d . . . . .
C22 C 0.3313(5) 0.5071(5) 0.4745(3) 0.0239(13) Uani 1 1 d . . . . .
C23 C 0.3499(6) 0.5256(6) 0.4107(3) 0.0344(16) Uani 1 1 d . . . . .
H23 H 0.3552 0.6112 0.3934 0.041 Uiso 1 1 calc R U . . .
C24 C 0.3607(6) 0.4149(6) 0.3716(3) 0.0375(17) Uani 1 1 d . . . . .
H24 H 0.3727 0.4249 0.3270 0.045 Uiso 1 1 calc R U . . .
C25 C 0.3540(6) 0.2936(6) 0.3975(3) 0.0348(16) Uani 1 1 d . . . . .
H25 H 0.3621 0.2181 0.3716 0.042 Uiso 1 1 calc R U . . .
C26 C 0.3351(5) 0.2811(6) 0.4625(3) 0.0272(14) Uani 1 1 d . . . . .
H26 H 0.3312 0.1959 0.4806 0.033 Uiso 1 1 calc R U . . .


_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
Br1 Ni1 2.5445(9) . ?
Ni1 N2 2.017(4) . ?
Ni1 N4 2.039(4) . ?
Ni1 N5 2.086(4) . ?
Ni1 N1 2.109(5) . ?
Ni1 N3 2.216(5) . ?
Cl1 O4 1.426(4) . ?
Cl1 O3 1.435(5) . ?
Cl1 O2 1.438(4) . ?
Cl1 O5 1.439(5) . ?
O1 C1 1.402(6) . ?
O1 H1 0.82(2) . ?
N1 C2 1.345(6) . ?
N1 C6 1.357(7) . ?
N2 C11 1.333(7) . ?
N2 C7 1.337(7) . ?
N3 C16 1.346(8) . ?
N3 C12 1.354(7) . ?
N4 C17 1.342(7) . ?
N4 C21 1.358(7) . ?
N5 C26 1.326(7) . ?
N5 C22 1.373(7) . ?
C1 C7 1.528(8) . ?
C1 C2 1.532(8) . ?
C1 C17 1.543(7) . ?
C2 C3 1.378(8) . ?
C3 C4 1.381(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.398(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.358(9) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.380(7) . ?
C8 C9 1.372(9) . ?
C8 H8 0.9500 . ?
C9 C10 1.397(9) . ?
C9 H9 0.9500 . ?
C10 C11 1.396(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.482(8) . ?
C12 C13 1.377(9) . ?
C13 C14 1.381(9) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(10) . ?
C14 H14 0.9500 . ?
C15 C16 1.377(10) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.387(8) . ?
C18 C19 1.383(9) . ?
C18 H18 0.9500 . ?
C19 C20 1.383(8) . ?
C19 H19 0.9500 . ?
C20 C21 1.386(7) . ?
C20 H20 0.9500 . ?
C21 C22 1.483(7) . ?
C22 C23 1.374(8) . ?
C23 C24 1.403(9) . ?
C23 H23 0.9500 . ?
C24 C25 1.355(9) . ?
C24 H24 0.9500 . ?
C25 C26 1.390(8) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

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
N2 Ni1 N4 87.01(18) . . ?
N2 Ni1 N5 156.47(19) . . ?
N4 Ni1 N5 79.21(17) . . ?
N2 Ni1 N1 89.33(18) . . ?
N4 Ni1 N1 79.09(18) . . ?
N5 Ni1 N1 106.45(19) . . ?
N2 Ni1 N3 75.67(18) . . ?
N4 Ni1 N3 111.98(19) . . ?
N5 Ni1 N3 91.82(18) . . ?
N1 Ni1 N3 160.42(17) . . ?
N2 Ni1 Br1 98.69(12) . . ?
N4 Ni1 Br1 166.78(15) . . ?
N5 Ni1 Br1 98.94(12) . . ?
N1 Ni1 Br1 89.00(11) . . ?
N3 Ni1 Br1 81.08(13) . . ?
O4 Cl1 O3 109.1(3) . . ?
O4 Cl1 O2 109.6(3) . . ?
O3 Cl1 O2 109.1(3) . . ?
O4 Cl1 O5 109.7(3) . . ?
O3 Cl1 O5 109.8(3) . . ?
O2 Cl1 O5 109.4(3) . . ?
C1 O1 H1 109.5 . . ?
C2 N1 C6 118.4(5) . . ?
C2 N1 Ni1 119.7(4) . . ?
C6 N1 Ni1 121.9(4) . . ?
C11 N2 C7 120.7(5) . . ?
C11 N2 Ni1 116.9(3) . . ?
C7 N2 Ni1 122.4(4) . . ?
C16 N3 C12 116.3(5) . . ?
C16 N3 Ni1 127.9(4) . . ?
C12 N3 Ni1 108.1(4) . . ?
C17 N4 C21 119.8(5) . . ?
C17 N4 Ni1 122.3(3) . . ?
C21 N4 Ni1 116.6(3) . . ?
C26 N5 C22 118.9(5) . . ?
C26 N5 Ni1 126.7(4) . . ?
C22 N5 Ni1 112.2(3) . . ?
O1 C1 C7 111.2(4) . . ?
O1 C1 C2 111.9(5) . . ?
C7 C1 C2 111.3(4) . . ?
O1 C1 C17 105.4(4) . . ?
C7 C1 C17 113.1(5) . . ?
C2 C1 C17 103.5(4) . . ?
N1 C2 C3 121.9(6) . . ?
N1 C2 C1 116.9(5) . . ?
C3 C2 C1 121.1(5) . . ?
C2 C3 C4 119.2(6) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 118.9(6) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C6 C5 C4 118.8(6) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
N1 C6 C5 122.6(6) . . ?
N1 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
N2 C7 C8 120.5(5) . . ?
N2 C7 C1 116.5(5) . . ?
C8 C7 C1 122.9(5) . . ?
C9 C8 C7 119.8(5) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 119.6(5) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 117.4(6) . . ?
C11 C10 H10 121.3 . . ?
C9 C10 H10 121.3 . . ?
N2 C11 C10 121.7(5) . . ?
N2 C11 C12 115.2(5) . . ?
C10 C11 C12 122.7(6) . . ?
N3 C12 C13 123.9(5) . . ?
N3 C12 C11 113.2(5) . . ?
C13 C12 C11 122.9(5) . . ?
C12 C13 C14 118.5(6) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 H13 120.7 . . ?
C13 C14 C15 118.4(6) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 H14 120.8 . . ?
C16 C15 C14 119.3(6) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
N3 C16 C15 123.2(6) . . ?
N3 C16 H16 118.4 . . ?
C15 C16 H16 118.4 . . ?
N4 C17 C18 121.2(5) . . ?
N4 C17 C1 115.8(4) . . ?
C18 C17 C1 122.4(5) . . ?
C19 C18 C17 118.9(6) . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C18 C19 C20 120.1(5) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C21 118.4(5) . . ?
C19 C20 H20 120.8 . . ?
C21 C20 H20 120.8 . . ?
N4 C21 C20 121.3(5) . . ?
N4 C21 C22 113.5(4) . . ?
C20 C21 C22 124.9(5) . . ?
N5 C22 C23 121.5(5) . . ?
N5 C22 C21 115.3(5) . . ?
C23 C22 C21 123.2(5) . . ?
C22 C23 C24 118.4(6) . . ?
C22 C23 H23 120.8 . . ?
C24 C23 H23 120.8 . . ?
C25 C24 C23 119.9(6) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C26 119.1(6) . . ?
C24 C25 H25 120.4 . . ?
C26 C25 H25 120.4 . . ?
N5 C26 C25 122.2(5) . . ?
N5 C26 H26 118.9 . . ?
C25 C26 H26 118.9 . . ?

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
C6 N1 C2 C3 -4.0(7) . . . . ?
Ni1 N1 C2 C3 177.0(4) . . . . ?
C6 N1 C2 C1 172.5(4) . . . . ?
Ni1 N1 C2 C1 -6.5(6) . . . . ?
O1 C1 C2 N1 -172.6(4) . . . . ?
C7 C1 C2 N1 62.2(6) . . . . ?
C17 C1 C2 N1 -59.6(6) . . . . ?
O1 C1 C2 C3 4.0(7) . . . . ?
C7 C1 C2 C3 -121.2(5) . . . . ?
C17 C1 C2 C3 117.0(5) . . . . ?
N1 C2 C3 C4 2.7(8) . . . . ?
C1 C2 C3 C4 -173.7(5) . . . . ?
C2 C3 C4 C5 0.4(8) . . . . ?
C3 C4 C5 C6 -2.1(9) . . . . ?
C2 N1 C6 C5 2.2(8) . . . . ?
Ni1 N1 C6 C5 -178.8(4) . . . . ?
C4 C5 C6 N1 0.9(9) . . . . ?
C11 N2 C7 C8 4.4(8) . . . . ?
Ni1 N2 C7 C8 -174.7(4) . . . . ?
C11 N2 C7 C1 -174.6(5) . . . . ?
Ni1 N2 C7 C1 6.3(6) . . . . ?
O1 C1 C7 N2 171.3(5) . . . . ?
C2 C1 C7 N2 -63.1(6) . . . . ?
C17 C1 C7 N2 52.9(6) . . . . ?
O1 C1 C7 C8 -7.6(7) . . . . ?
C2 C1 C7 C8 117.9(6) . . . . ?
C17 C1 C7 C8 -126.0(6) . . . . ?
N2 C7 C8 C9 -0.2(9) . . . . ?
C1 C7 C8 C9 178.8(6) . . . . ?
C7 C8 C9 C10 -3.6(10) . . . . ?
C8 C9 C10 C11 3.2(10) . . . . ?
C7 N2 C11 C10 -4.8(8) . . . . ?
Ni1 N2 C11 C10 174.3(4) . . . . ?
C7 N2 C11 C12 167.6(5) . . . . ?
Ni1 N2 C11 C12 -13.3(6) . . . . ?
C9 C10 C11 N2 0.9(9) . . . . ?
C9 C10 C11 C12 -170.9(6) . . . . ?
C16 N3 C12 C13 4.3(9) . . . . ?
Ni1 N3 C12 C13 -147.8(5) . . . . ?
C16 N3 C12 C11 -176.9(5) . . . . ?
Ni1 N3 C12 C11 31.0(6) . . . . ?
N2 C11 C12 N3 -14.2(7) . . . . ?
C10 C11 C12 N3 158.1(5) . . . . ?
N2 C11 C12 C13 164.5(6) . . . . ?
C10 C11 C12 C13 -23.2(9) . . . . ?
N3 C12 C13 C14 -0.6(10) . . . . ?
C11 C12 C13 C14 -179.3(6) . . . . ?
C12 C13 C14 C15 -4.7(10) . . . . ?
C13 C14 C15 C16 6.2(11) . . . . ?
C12 N3 C16 C15 -2.7(10) . . . . ?
Ni1 N3 C16 C15 143.0(6) . . . . ?
C14 C15 C16 N3 -2.5(11) . . . . ?
C21 N4 C17 C18 6.4(9) . . . . ?
Ni1 N4 C17 C18 172.8(4) . . . . ?
C21 N4 C17 C1 -164.5(5) . . . . ?
Ni1 N4 C17 C1 1.8(7) . . . . ?
O1 C1 C17 N4 -179.0(5) . . . . ?
C7 C1 C17 N4 -57.2(7) . . . . ?
C2 C1 C17 N4 63.4(6) . . . . ?
O1 C1 C17 C18 10.2(7) . . . . ?
C7 C1 C17 C18 131.9(6) . . . . ?
C2 C1 C17 C18 -107.5(6) . . . . ?
N4 C17 C18 C19 -3.0(9) . . . . ?
C1 C17 C18 C19 167.3(6) . . . . ?
C17 C18 C19 C20 -1.7(10) . . . . ?
C18 C19 C20 C21 3.0(10) . . . . ?
C17 N4 C21 C20 -5.1(9) . . . . ?
Ni1 N4 C21 C20 -172.2(5) . . . . ?
C17 N4 C21 C22 168.4(5) . . . . ?
Ni1 N4 C21 C22 1.3(7) . . . . ?
C19 C20 C21 N4 0.4(9) . . . . ?
C19 C20 C21 C22 -172.3(6) . . . . ?
C26 N5 C22 C23 1.7(10) . . . . ?
Ni1 N5 C22 C23 -162.2(5) . . . . ?
C26 N5 C22 C21 -175.8(5) . . . . ?
Ni1 N5 C22 C21 20.3(7) . . . . ?
N4 C21 C22 N5 -14.6(8) . . . . ?
C20 C21 C22 N5 158.6(6) . . . . ?
N4 C21 C22 C23 167.9(6) . . . . ?
C20 C21 C22 C23 -18.9(10) . . . . ?
N5 C22 C23 C24 -0.5(11) . . . . ?
C21 C22 C23 C24 176.8(6) . . . . ?
C22 C23 C24 C25 -0.7(11) . . . . ?
C23 C24 C25 C26 0.7(11) . . . . ?
C22 N5 C26 C25 -1.8(10) . . . . ?
Ni1 N5 C26 C25 159.5(5) . . . . ?
C24 C25 C26 N5 0.6(11) . . . . ?

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
O1 H1 Br1 0.82 2.45 3.253(4) 164.7 2_556

_refine_diff_density_max         0.857
_refine_diff_density_min         -1.521
_refine_diff_density_rms         0.153

####################################################################### 
# 
# 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_14
_database_code_depnum_ccdc_archive 'CCDC 1470089'
_audit_update_record             
;
2016-03-22 deposited with the CCDC.
2016-05-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H22 Cd N6 O, 2(Cl O4), C2 H3 N'
_chemical_formula_sum            'C30 H25 Cd Cl2 N7 O9'
_chemical_formula_weight         810.87

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'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.8927(2)
_cell_length_b                   12.4047(3)
_cell_length_c                   20.9303(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.3110(10)
_cell_angle_gamma                90
_cell_volume                     3270.41(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    25517
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_F_000             1632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.896
_shelx_estimated_absorpt_T_min   0.855
_shelx_estimated_absorpt_T_max   0.900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.846
_exptl_absorpt_correction_T_max  0.945
_exptl_absorpt_process_details   'Sortav (Blessing, 1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'profile from ω scans'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            25129
_diffrn_reflns_av_unetI/netI     0.0783
_diffrn_reflns_av_R_equivalents  0.0785
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.080
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             7447
_reflns_number_gt                5110
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997
;
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0561P)²+3.4875P] 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         7447
_refine_ls_number_parameters     512
_refine_ls_number_restraints     200
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1254
_refine_ls_wR_factor_gt          0.1087
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_restrained_S_all      0.982
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.72090(2) 0.68115(2) 0.53003(2) 0.02960(11) Uani 1 1 d . . . . .
Cl1 Cl 0.60014(10) 0.66749(9) 0.17516(5) 0.0433(3) Uani 1 1 d . . . . .
Cl2 Cl 0.63515(9) 0.80506(9) 0.78733(5) 0.0392(3) Uani 1 1 d . . . . .
O1 O 0.7472(2) 0.5116(2) 0.32861(13) 0.0385(7) Uani 1 1 d D . . . .
H1 H 0.712(3) 0.545(2) 0.2966(8) 0.058 Uiso 1 1 calc DR U . . .
O2 O 0.6063(4) 0.5744(3) 0.21521(19) 0.0608(13) Uani 0.839(5) 1 d D U P A 1
O3 O 0.5483(5) 0.7529(5) 0.1967(3) 0.0970(19) Uani 0.839(5) 1 d D U P A 1
O4 O 0.7083(4) 0.7007(5) 0.1771(3) 0.1007(19) Uani 0.839(5) 1 d D U P A 1
O5 O 0.5517(5) 0.6434(3) 0.10963(19) 0.0630(14) Uani 0.839(5) 1 d D U P A 1
O2A O 0.537(2) 0.5619(16) 0.1883(10) 0.067(4) Uani 0.161(5) 1 d D U P A 2
O3A O 0.508(2) 0.7402(19) 0.1615(13) 0.076(4) Uani 0.161(5) 1 d D U P A 2
O4A O 0.661(2) 0.690(2) 0.2322(12) 0.088(3) Uani 0.161(5) 1 d D U P A 2
O5A O 0.631(2) 0.6467(19) 0.1210(11) 0.063(4) Uani 0.161(5) 1 d D U P A 2
O6 O 0.7010(3) 0.8556(3) 0.74899(16) 0.0572(9) Uani 1 1 d . . . . .
O7 O 0.5967(3) 0.7037(3) 0.75803(16) 0.0610(10) Uani 1 1 d . . . . .
O8 O 0.6959(3) 0.7850(3) 0.85212(15) 0.0501(8) Uani 1 1 d . . . . .
O9 O 0.5480(3) 0.8752(3) 0.79091(18) 0.0652(10) Uani 1 1 d . . . . .
N1 N 0.8089(3) 0.5263(3) 0.50458(15) 0.0308(8) Uani 1 1 d . . . . .
N2 N 0.7866(3) 0.7402(3) 0.44077(16) 0.0309(8) Uani 1 1 d . . . . .
N3 N 0.7913(3) 0.8521(3) 0.55261(17) 0.0385(9) Uani 1 1 d . . . . .
N4 N 0.5941(3) 0.6159(2) 0.44243(15) 0.0289(7) Uani 1 1 d . . . . .
N5 N 0.5529(3) 0.7072(3) 0.55148(16) 0.0320(8) Uani 1 1 d . . . . .
N6 N 0.7829(3) 0.6431(3) 0.64159(18) 0.0449(9) Uani 1 1 d . . . . .
C1 C 0.7381(3) 0.5637(3) 0.38704(18) 0.0301(9) Uani 1 1 d . . . . .
C2 C 0.8072(3) 0.4984(3) 0.44236(19) 0.0292(9) Uani 1 1 d . . . . .
C3 C 0.8684(3) 0.4134(3) 0.4273(2) 0.0345(9) Uani 1 1 d . . . . .
H3 H 0.8670 0.3952 0.3830 0.041 Uiso 1 1 calc R U . . .
C4 C 0.9311(4) 0.3558(4) 0.4776(2) 0.0413(11) Uani 1 1 d . . . . .
H4 H 0.9726 0.2971 0.4681 0.050 Uiso 1 1 calc R U . . .
C5 C 0.9332(3) 0.3836(3) 0.5412(2) 0.0378(10) Uani 1 1 d . . . . .
H5 H 0.9758 0.3448 0.5764 0.045 Uiso 1 1 calc R U . . .
C6 C 0.8712(3) 0.4700(3) 0.5528(2) 0.0347(10) Uani 1 1 d . . . . .
H6 H 0.8730 0.4902 0.5968 0.042 Uiso 1 1 calc R U . . .
C7 C 0.7844(3) 0.6782(3) 0.38792(19) 0.0321(9) Uani 1 1 d . . . . .
C8 C 0.8277(4) 0.7146(4) 0.3362(2) 0.0435(11) Uani 1 1 d . . . . .
H8 H 0.8260 0.6704 0.2989 0.052 Uiso 1 1 calc R U . . .
C9 C 0.8732(4) 0.8161(4) 0.3402(2) 0.0543(14) Uani 1 1 d . . . . .
H9 H 0.9042 0.8419 0.3058 0.065 Uiso 1 1 calc R U . . .
C10 C 0.8735(4) 0.8797(4) 0.3943(2) 0.0505(13) Uani 1 1 d . . . . .
H10 H 0.9036 0.9498 0.3974 0.061 Uiso 1 1 calc R U . . .
C11 C 0.8289(3) 0.8393(3) 0.4443(2) 0.0345(10) Uani 1 1 d . . . . .
C12 C 0.8251(3) 0.9035(3) 0.5038(2) 0.0373(10) Uani 1 1 d . . . . .
C13 C 0.8532(4) 1.0120(4) 0.5096(2) 0.0472(12) Uani 1 1 d . . . . .
H13 H 0.8738 1.0486 0.4744 0.057 Uiso 1 1 calc R U . . .
C14 C 0.8508(4) 1.0661(4) 0.5673(2) 0.0538(13) Uani 1 1 d . . . . .
H14 H 0.8701 1.1400 0.5719 0.065 Uiso 1 1 calc R U . . .
C15 C 0.8205(4) 1.0124(4) 0.6178(2) 0.0552(14) Uani 1 1 d . . . . .
H15 H 0.8198 1.0476 0.6580 0.066 Uiso 1 1 calc R U . . .
C16 C 0.7912(4) 0.9053(4) 0.6081(2) 0.0499(13) Uani 1 1 d . . . . .
H16 H 0.7699 0.8677 0.6427 0.060 Uiso 1 1 calc R U . . .
C17 C 0.6200(3) 0.5636(3) 0.39193(18) 0.0287(9) Uani 1 1 d . . . . .
C18 C 0.5443(4) 0.5113(3) 0.34533(19) 0.0370(10) Uani 1 1 d . . . . .
H18 H 0.5645 0.4712 0.3112 0.044 Uiso 1 1 calc R U . . .
C19 C 0.4395(4) 0.5184(4) 0.3494(2) 0.0450(11) Uani 1 1 d . . . . .
H19 H 0.3863 0.4840 0.3175 0.054 Uiso 1 1 calc R U . . .
C20 C 0.4115(3) 0.5752(4) 0.3995(2) 0.0395(10) Uani 1 1 d . . . . .
H20 H 0.3391 0.5824 0.4019 0.047 Uiso 1 1 calc R U . . .
C21 C 0.4912(3) 0.6219(3) 0.44645(19) 0.0305(9) Uani 1 1 d . . . . .
C22 C 0.4682(3) 0.6813(3) 0.50396(19) 0.0297(9) Uani 1 1 d . . . . .
C23 C 0.3659(3) 0.7071(3) 0.5094(2) 0.0377(10) Uani 1 1 d . . . . .
H23 H 0.3072 0.6901 0.4751 0.045 Uiso 1 1 calc R U . . .
C24 C 0.3502(4) 0.7577(4) 0.5655(2) 0.0436(11) Uani 1 1 d . . . . .
H24 H 0.2807 0.7762 0.5701 0.052 Uiso 1 1 calc R U . . .
C25 C 0.4370(4) 0.7810(4) 0.6147(2) 0.0406(11) Uani 1 1 d . . . . .
H25 H 0.4280 0.8142 0.6540 0.049 Uiso 1 1 calc R U . . .
C26 C 0.5373(4) 0.7553(4) 0.6058(2) 0.0411(11) Uani 1 1 d . . . . .
H26 H 0.5971 0.7723 0.6394 0.049 Uiso 1 1 calc R U . . .
C27 C 0.8204(4) 0.6410(4) 0.6954(2) 0.0428(11) Uani 1 1 d . . . . .
C28 C 0.8722(5) 0.6376(5) 0.7646(2) 0.0722(17) Uani 1 1 d . . . . .
H28A H 0.8906 0.5630 0.7775 0.108 Uiso 1 1 calc R U . . .
H28B H 0.8239 0.6663 0.7907 0.108 Uiso 1 1 calc R U . . .
H28C H 0.9370 0.6814 0.7719 0.108 Uiso 1 1 calc R U . . .
N7 N 0.5821(10) 0.8881(11) 0.3929(6) 0.076(3) Uani 0.593(6) 1 d D U P B -1
C29 C 0.6086(7) 0.9183(8) 0.3494(4) 0.057(2) Uani 0.593(6) 1 d D U P B -1
C30 C 0.6398(6) 0.9599(7) 0.2919(4) 0.052(2) Uani 0.593(6) 1 d D U P B -1
H30A H 0.6518 0.8998 0.2639 0.078 Uiso 0.593(6) 1 calc R U P B -1
H30B H 0.7054 1.0017 0.3050 0.078 Uiso 0.593(6) 1 calc R U P B -1
H30C H 0.5835 1.0064 0.2677 0.078 Uiso 0.593(6) 1 calc R U P B -1
N8 N 0.5543(15) 0.8807(17) 0.4084(9) 0.075(3) Uani 0.407(6) 1 d D U P B -2
C31 C 0.5293(12) 0.9356(12) 0.4441(7) 0.068(3) Uani 0.407(6) 1 d D U P B -2
C32 C 0.5213(15) 0.998(2) 0.5041(11) 0.067(4) Uani 0.407(6) 1 d D U P B -2
H32A H 0.5200 1.0751 0.4946 0.101 Uiso 0.407(6) 1 calc R U P B -2
H32B H 0.5827 0.9812 0.5393 0.101 Uiso 0.407(6) 1 calc R U P B -2
H32C H 0.4559 0.9775 0.5179 0.101 Uiso 0.407(6) 1 calc R U P B -2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 N3 2.315(3) . ?
Cd1 N4 2.326(3) . ?
Cd1 N5 2.327(3) . ?
Cd1 N2 2.328(3) . ?
Cd1 N6 2.349(4) . ?
Cd1 N1 2.350(3) . ?
Cl1 O5A 1.306(18) . ?
Cl1 O4A 1.31(2) . ?
Cl1 O3 1.380(5) . ?
Cl1 O5 1.413(4) . ?
Cl1 O2 1.419(4) . ?
Cl1 O4 1.446(5) . ?
Cl1 O3A 1.47(2) . ?
Cl1 O2A 1.598(18) . ?
Cl2 O6 1.431(3) . ?
Cl2 O9 1.436(4) . ?
Cl2 O8 1.436(3) . ?
Cl2 O7 1.439(3) . ?
O1 C1 1.410(4) . ?
O1 H1 0.837(19) . ?
N1 C2 1.343(5) . ?
N1 C6 1.343(5) . ?
N2 C11 1.340(5) . ?
N2 C7 1.343(5) . ?
N3 C16 1.336(5) . ?
N3 C12 1.353(5) . ?
N4 C17 1.341(5) . ?
N4 C21 1.349(5) . ?
N5 C26 1.337(5) . ?
N5 C22 1.349(5) . ?
N6 C27 1.127(5) . ?
C1 C2 1.533(6) . ?
C1 C7 1.538(6) . ?
C1 C17 1.549(5) . ?
C2 C3 1.393(5) . ?
C3 C4 1.382(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.370(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.394(5) . ?
C8 C9 1.385(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.380(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.488(6) . ?
C12 C13 1.392(6) . ?
C13 C14 1.388(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.374(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(7) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.385(6) . ?
C18 C19 1.375(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.374(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.388(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.495(5) . ?
C22 C23 1.384(6) . ?
C23 C24 1.385(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.379(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.382(6) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.460(7) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
N7 C29 1.103(11) . ?
C29 C30 1.444(9) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
N8 C31 1.109(13) . ?
C31 C32 1.496(14) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?

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 Cd1 N4 131.20(12) . . ?
N3 Cd1 N5 100.02(12) . . ?
N4 Cd1 N5 70.95(11) . . ?
N3 Cd1 N2 71.43(12) . . ?
N4 Cd1 N2 77.99(11) . . ?
N5 Cd1 N2 128.62(11) . . ?
N3 Cd1 N6 86.89(13) . . ?
N4 Cd1 N6 138.29(12) . . ?
N5 Cd1 N6 88.26(12) . . ?
N2 Cd1 N6 139.12(13) . . ?
N3 Cd1 N1 127.44(12) . . ?
N4 Cd1 N1 80.16(11) . . ?
N5 Cd1 N1 132.21(11) . . ?
N2 Cd1 N1 78.44(11) . . ?
N6 Cd1 N1 89.00(12) . . ?
O5A Cl1 O4A 126.4(17) . . ?
O3 Cl1 O5 109.6(3) . . ?
O3 Cl1 O2 113.7(3) . . ?
O5 Cl1 O2 111.0(3) . . ?
O3 Cl1 O4 107.7(4) . . ?
O5 Cl1 O4 108.2(3) . . ?
O2 Cl1 O4 106.4(3) . . ?
O5A Cl1 O3A 109.8(14) . . ?
O4A Cl1 O3A 110.7(15) . . ?
O5A Cl1 O2A 104.5(12) . . ?
O4A Cl1 O2A 104.2(11) . . ?
O3A Cl1 O2A 96.6(12) . . ?
O6 Cl2 O9 109.2(2) . . ?
O6 Cl2 O8 109.7(2) . . ?
O9 Cl2 O8 109.3(2) . . ?
O6 Cl2 O7 109.6(2) . . ?
O9 Cl2 O7 110.4(2) . . ?
O8 Cl2 O7 108.7(2) . . ?
C1 O1 H1 109.5 . . ?
C2 N1 C6 118.5(3) . . ?
C2 N1 Cd1 121.4(3) . . ?
C6 N1 Cd1 119.7(3) . . ?
C11 N2 C7 120.5(3) . . ?
C11 N2 Cd1 117.2(3) . . ?
C7 N2 Cd1 122.2(3) . . ?
C16 N3 C12 118.9(4) . . ?
C16 N3 Cd1 123.8(3) . . ?
C12 N3 Cd1 117.0(3) . . ?
C17 N4 C21 119.3(3) . . ?
C17 N4 Cd1 122.6(3) . . ?
C21 N4 Cd1 117.8(2) . . ?
C26 N5 C22 119.2(4) . . ?
C26 N5 Cd1 122.7(3) . . ?
C22 N5 Cd1 117.7(2) . . ?
C27 N6 Cd1 168.6(4) . . ?
O1 C1 C2 105.7(3) . . ?
O1 C1 C7 109.3(3) . . ?
C2 C1 C7 108.5(3) . . ?
O1 C1 C17 108.7(3) . . ?
C2 C1 C17 111.7(3) . . ?
C7 C1 C17 112.6(3) . . ?
N1 C2 C3 121.4(4) . . ?
N1 C2 C1 118.9(3) . . ?
C3 C2 C1 119.7(3) . . ?
C4 C3 C2 119.1(4) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C5 C4 C3 119.8(4) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 118.1(4) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
N1 C6 C5 123.0(4) . . ?
N1 C6 H6 118.5 . . ?
C5 C6 H6 118.5 . . ?
N2 C7 C8 120.8(4) . . ?
N2 C7 C1 118.6(3) . . ?
C8 C7 C1 120.5(4) . . ?
C9 C8 C7 118.8(4) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C10 C9 C8 119.7(4) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 118.9(4) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
N2 C11 C10 121.2(4) . . ?
N2 C11 C12 116.9(3) . . ?
C10 C11 C12 122.0(4) . . ?
N3 C12 C13 120.7(4) . . ?
N3 C12 C11 116.9(4) . . ?
C13 C12 C11 122.4(4) . . ?
C14 C13 C12 119.2(4) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C15 C14 C13 119.8(4) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 117.8(4) . . ?
C14 C15 H15 121.1 . . ?
C16 C15 H15 121.1 . . ?
N3 C16 C15 123.4(4) . . ?
N3 C16 H16 118.3 . . ?
C15 C16 H16 118.3 . . ?
N4 C17 C18 121.7(4) . . ?
N4 C17 C1 117.7(3) . . ?
C18 C17 C1 120.6(3) . . ?
C19 C18 C17 118.7(4) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
C20 C19 C18 120.1(4) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 118.7(4) . . ?
C19 C20 H20 120.7 . . ?
C21 C20 H20 120.7 . . ?
N4 C21 C20 121.5(4) . . ?
N4 C21 C22 116.4(3) . . ?
C20 C21 C22 122.2(4) . . ?
N5 C22 C23 121.3(4) . . ?
N5 C22 C21 116.3(3) . . ?
C23 C22 C21 122.4(4) . . ?
C22 C23 C24 119.3(4) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
C25 C24 C23 119.0(4) . . ?
C25 C24 H24 120.5 . . ?
C23 C24 H24 120.5 . . ?
C24 C25 C26 119.0(4) . . ?
C24 C25 H25 120.5 . . ?
C26 C25 H25 120.5 . . ?
N5 C26 C25 122.1(4) . . ?
N5 C26 H26 119.0 . . ?
C25 C26 H26 119.0 . . ?
N6 C27 C28 178.2(5) . . ?
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 . . ?
N7 C29 C30 178.0(11) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N8 C31 C32 164.6(19) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

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
C6 N1 C2 C3 -0.2(5) . . . . ?
Cd1 N1 C2 C3 173.1(3) . . . . ?
C6 N1 C2 C1 -178.7(3) . . . . ?
Cd1 N1 C2 C1 -5.4(5) . . . . ?
O1 C1 C2 N1 -176.2(3) . . . . ?
C7 C1 C2 N1 66.7(4) . . . . ?
C17 C1 C2 N1 -58.1(4) . . . . ?
O1 C1 C2 C3 5.2(5) . . . . ?
C7 C1 C2 C3 -111.9(4) . . . . ?
C17 C1 C2 C3 123.3(4) . . . . ?
N1 C2 C3 C4 0.8(6) . . . . ?
C1 C2 C3 C4 179.3(4) . . . . ?
C2 C3 C4 C5 -0.7(6) . . . . ?
C3 C4 C5 C6 0.0(6) . . . . ?
C2 N1 C6 C5 -0.6(6) . . . . ?
Cd1 N1 C6 C5 -174.0(3) . . . . ?
C4 C5 C6 N1 0.7(6) . . . . ?
C11 N2 C7 C8 1.1(6) . . . . ?
Cd1 N2 C7 C8 -177.8(3) . . . . ?
C11 N2 C7 C1 178.2(4) . . . . ?
Cd1 N2 C7 C1 -0.8(5) . . . . ?
O1 C1 C7 N2 -177.8(3) . . . . ?
C2 C1 C7 N2 -63.0(4) . . . . ?
C17 C1 C7 N2 61.2(5) . . . . ?
O1 C1 C7 C8 -0.8(5) . . . . ?
C2 C1 C7 C8 114.0(4) . . . . ?
C17 C1 C7 C8 -121.7(4) . . . . ?
N2 C7 C8 C9 0.1(7) . . . . ?
C1 C7 C8 C9 -176.9(4) . . . . ?
C7 C8 C9 C10 -1.0(8) . . . . ?
C8 C9 C10 C11 0.8(8) . . . . ?
C7 N2 C11 C10 -1.3(6) . . . . ?
Cd1 N2 C11 C10 177.6(4) . . . . ?
C7 N2 C11 C12 178.3(4) . . . . ?
Cd1 N2 C11 C12 -2.7(5) . . . . ?
C9 C10 C11 N2 0.3(7) . . . . ?
C9 C10 C11 C12 -179.3(5) . . . . ?
C16 N3 C12 C13 -3.9(7) . . . . ?
Cd1 N3 C12 C13 170.1(4) . . . . ?
C16 N3 C12 C11 177.0(4) . . . . ?
Cd1 N3 C12 C11 -9.0(5) . . . . ?
N2 C11 C12 N3 7.8(6) . . . . ?
C10 C11 C12 N3 -172.5(4) . . . . ?
N2 C11 C12 C13 -171.2(4) . . . . ?
C10 C11 C12 C13 8.4(7) . . . . ?
N3 C12 C13 C14 2.9(7) . . . . ?
C11 C12 C13 C14 -178.1(4) . . . . ?
C12 C13 C14 C15 -0.2(8) . . . . ?
C13 C14 C15 C16 -1.3(8) . . . . ?
C12 N3 C16 C15 2.4(8) . . . . ?
Cd1 N3 C16 C15 -171.2(4) . . . . ?
C14 C15 C16 N3 0.2(8) . . . . ?
C21 N4 C17 C18 -3.0(5) . . . . ?
Cd1 N4 C17 C18 170.1(3) . . . . ?
C21 N4 C17 C1 176.8(3) . . . . ?
Cd1 N4 C17 C1 -10.1(4) . . . . ?
O1 C1 C17 N4 -175.8(3) . . . . ?
C2 C1 C17 N4 67.9(4) . . . . ?
C7 C1 C17 N4 -54.6(4) . . . . ?
O1 C1 C17 C18 4.0(5) . . . . ?
C2 C1 C17 C18 -112.3(4) . . . . ?
C7 C1 C17 C18 125.2(4) . . . . ?
N4 C17 C18 C19 3.5(6) . . . . ?
C1 C17 C18 C19 -176.3(4) . . . . ?
C17 C18 C19 C20 -1.0(7) . . . . ?
C18 C19 C20 C21 -1.9(7) . . . . ?
C17 N4 C21 C20 -0.1(6) . . . . ?
Cd1 N4 C21 C20 -173.5(3) . . . . ?
C17 N4 C21 C22 -180.0(3) . . . . ?
Cd1 N4 C21 C22 6.6(4) . . . . ?
C19 C20 C21 N4 2.5(6) . . . . ?
C19 C20 C21 C22 -177.6(4) . . . . ?
C26 N5 C22 C23 2.3(6) . . . . ?
Cd1 N5 C22 C23 -171.6(3) . . . . ?
C26 N5 C22 C21 -176.4(4) . . . . ?
Cd1 N5 C22 C21 9.6(4) . . . . ?
N4 C21 C22 N5 -10.8(5) . . . . ?
C20 C21 C22 N5 169.3(4) . . . . ?
N4 C21 C22 C23 170.5(4) . . . . ?
C20 C21 C22 C23 -9.4(6) . . . . ?
N5 C22 C23 C24 -1.7(6) . . . . ?
C21 C22 C23 C24 176.9(4) . . . . ?
C22 C23 C24 C25 -0.2(6) . . . . ?
C23 C24 C25 C26 1.5(7) . . . . ?
C22 N5 C26 C25 -1.0(6) . . . . ?
Cd1 N5 C26 C25 172.7(3) . . . . ?
C24 C25 C26 N5 -0.9(7) . . . . ?

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
O1 H1 O2 0.84 1.97 2.775(5) 160.1 .
O1 H1 O4A 0.84 2.25 3.04(3) 156.0 .

_refine_diff_density_max         0.571
_refine_diff_density_min         -0.657
_refine_diff_density_rms         0.104

