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

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1422671'
_audit_update_record             
;
2015-09-05 deposited with the CCDC.
2015-12-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 Co N16'
_chemical_formula_weight         512.37

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   8.3406(2)
_cell_length_b                   15.9601(4)
_cell_length_c                   16.1633(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2151.61(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      1.79
_cell_measurement_theta_max      27.54

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1040.0
_exptl_absorpt_coefficient_mu    0.844
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.877
_exptl_absorpt_correction_T_max  0.911
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean none
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            30815
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_av_sigmaI/netI    0.0668
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         27.54
_reflns_number_total             4971
_reflns_number_gt                3619
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0329P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.000(14)
_refine_ls_number_reflns         4939
_refine_ls_number_parameters     317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.0770
_refine_ls_wR_factor_gt          0.0690
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_refine_ls_shift/su_max          0.032
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.08636(4) 0.58928(2) 0.12968(2) 0.02894(11) Uani 1 1 d . . .
N5 N 0.2781(3) 0.65411(14) 0.12662(16) 0.0320(6) Uani 1 1 d . . .
N6 N 0.4166(3) 0.61770(13) 0.13904(15) 0.0363(6) Uani 1 1 d . . .
N7 N 0.2359(3) 0.50278(15) 0.15001(13) 0.0281(6) Uani 1 1 d . . .
N8 N 0.4908(3) 0.47767(15) 0.17566(15) 0.0368(6) Uani 1 1 d . . .
H8 H 0.5923 0.4855 0.1810 0.044 Uiso 1 1 calc R . .
N1 N -0.0037(3) 0.69674(15) 0.10778(15) 0.0376(7) Uani 1 1 d . . .
N4 N 0.2737(3) 0.73415(16) 0.11364(17) 0.0448(7) Uani 1 1 d . . .
N2 N -0.0989(4) 0.81849(18) 0.08022(17) 0.0590(8) Uani 1 1 d . . .
H2 H -0.1677 0.8571 0.0695 0.071 Uiso 1 1 calc R . .
N3 N 0.0614(4) 0.83184(16) 0.08620(18) 0.0566(8) Uani 1 1 d . . .
N13 N -0.1087(3) 0.52758(13) 0.13199(16) 0.0326(5) Uani 1 1 d . . .
N15 N 0.0419(3) 0.59458(15) 0.24553(13) 0.0314(6) Uani 1 1 d . . .
N9 N 0.0688(3) 0.55945(14) 0.01702(14) 0.0328(6) Uani 1 1 d . . .
N16 N -0.1315(3) 0.55780(16) 0.34285(15) 0.0404(7) Uani 1 1 d . . .
H16 H -0.2154 0.5368 0.3658 0.049 Uiso 1 1 calc R . .
N12 N -0.1695(3) 0.49693(18) 0.06569(16) 0.0438(7) Uani 1 1 d . . .
C14 C -0.0077(4) 0.60018(19) 0.38235(19) 0.0374(7) Uani 1 1 d . . .
N14 N -0.1856(3) 0.51744(17) 0.20267(16) 0.0378(7) Uani 1 1 d . . .
N11 N -0.0786(4) 0.49502(17) -0.07776(16) 0.0503(7) Uani 1 1 d . . .
C5 C 0.4100(4) 0.40319(17) 0.18879(16) 0.0336(6) Uani 1 1 d . . .
C2 C 0.1146(4) 0.75590(19) 0.10296(18) 0.0426(8) Uani 1 1 d . . .
C4 C 0.2479(3) 0.41929(19) 0.17313(17) 0.0311(7) Uani 1 1 d . . .
C3 C 0.3835(3) 0.53505(18) 0.15324(17) 0.0312(7) Uani 1 1 d . . .
C6 C 0.4611(4) 0.3253(2) 0.2150(2) 0.0489(9) Uani 1 1 d . . .
H6 H 0.5684 0.3149 0.2267 0.059 Uiso 1 1 calc R . .
C1 C -0.1363(4) 0.7397(2) 0.0926(2) 0.0494(10) Uani 1 1 d . . .
H1 H -0.2393 0.7175 0.0910 0.059 Uiso 1 1 calc R . .
C8 C 0.1871(5) 0.2799(2) 0.2063(2) 0.0525(10) Uani 1 1 d . . .
H8A H 0.1134 0.2365 0.2118 0.063 Uiso 1 1 calc R . .
C9 C 0.1348(4) 0.35726(18) 0.1822(2) 0.0403(8) Uani 1 1 d . . .
H9 H 0.0267 0.3676 0.1723 0.048 Uiso 1 1 calc R . .
C7 C 0.3487(5) 0.2646(2) 0.2229(2) 0.0580(10) Uani 1 1 d . . .
H7 H 0.3800 0.2114 0.2399 0.070 Uiso 1 1 calc R . .
C11 C -0.0641(4) 0.51690(19) 0.00111(19) 0.0374(7) Uani 1 1 d . . .
N10 N 0.1511(3) 0.56722(16) -0.05521(16) 0.0432(7) Uani 1 1 d . . .
C12 C -0.0951(4) 0.55608(17) 0.26257(17) 0.0329(7) Uani 1 1 d . . .
C13 C 0.1018(4) 0.62260(17) 0.32121(17) 0.0333(7) Uani 1 1 d . . .
C18 C 0.2389(4) 0.6665(2) 0.3397(2) 0.0461(9) Uani 1 1 d . . .
H18 H 0.3133 0.6804 0.2991 0.055 Uiso 1 1 calc R . .
C15 C 0.0149(5) 0.6230(2) 0.4638(2) 0.0561(10) Uani 1 1 d . . .
H15 H -0.0581 0.6080 0.5047 0.067 Uiso 1 1 calc R . .
C16 C 0.1491(5) 0.6685(2) 0.4818(2) 0.0627(11) Uani 1 1 d . . .
H16A H 0.1661 0.6862 0.5359 0.075 Uiso 1 1 calc R . .
C17 C 0.2611(5) 0.6890(2) 0.4212(2) 0.0626(11) Uani 1 1 d . . .
H17 H 0.3529 0.7185 0.4361 0.075 Uiso 1 1 calc R . .
C10 C 0.0575(4) 0.5274(2) -0.10883(19) 0.0538(10) Uani 1 1 d . . .
H10 H 0.0844 0.5223 -0.1644 0.065 Uiso 1 1 calc R . .


_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 N9 1.888(2) . ?
Co1 N7 1.889(2) . ?
Co1 N13 1.902(2) . ?
Co1 N5 1.906(2) . ?
Co1 N1 1.906(2) . ?
Co1 N15 1.911(2) . ?
N5 N4 1.295(3) . ?
N5 N6 1.309(3) . ?
N6 C3 1.367(3) . ?
N7 C3 1.336(3) . ?
N7 C4 1.388(4) . ?
N8 C3 1.331(3) . ?
N8 C5 1.383(3) . ?
N8 H8 0.8600 . ?
N1 C1 1.324(4) . ?
N1 C2 1.368(4) . ?
N4 C2 1.383(4) . ?
N2 C1 1.311(4) . ?
N2 N3 1.357(4) . ?
N2 H2 0.8600 . ?
N3 C2 1.319(4) . ?
N13 N12 1.283(3) . ?
N13 N14 1.320(3) . ?
N15 C12 1.326(3) . ?
N15 C13 1.395(3) . ?
N9 C11 1.325(4) . ?
N9 N10 1.360(3) . ?
N16 C12 1.333(3) . ?
N16 C14 1.390(4) . ?
N16 H16 0.8600 . ?
N12 C11 1.401(4) . ?
C14 C15 1.378(4) . ?
C14 C13 1.393(4) . ?
N14 C12 1.374(4) . ?
N11 C11 1.327(4) . ?
N11 C10 1.345(4) . ?
C5 C6 1.381(4) . ?
C5 C4 1.399(4) . ?
C4 C9 1.376(4) . ?
C6 C7 1.353(5) . ?
C6 H6 0.9300 . ?
C1 H1 0.9300 . ?
C8 C9 1.366(4) . ?
C8 C7 1.396(5) . ?
C8 H8A 0.9300 . ?
C9 H9 0.9300 . ?
C7 H7 0.9300 . ?
N10 C10 1.328(4) . ?
C13 C18 1.374(4) . ?
C18 C17 1.378(5) . ?
C18 H18 0.9300 . ?
C15 C16 1.366(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.392(5) . ?
C16 H16A 0.9300 . ?
C17 H17 0.9300 . ?
C10 H10 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N9 Co1 N7 91.98(10) . . ?
N9 Co1 N13 79.75(11) . . ?
N7 Co1 N13 100.53(10) . . ?
N9 Co1 N5 100.19(11) . . ?
N7 Co1 N5 81.22(10) . . ?
N13 Co1 N5 178.25(10) . . ?
N9 Co1 N1 90.99(10) . . ?
N7 Co1 N1 161.86(11) . . ?
N13 Co1 N1 97.61(10) . . ?
N5 Co1 N1 80.65(11) . . ?
N9 Co1 N15 160.29(9) . . ?
N7 Co1 N15 89.42(9) . . ?
N13 Co1 N15 80.66(10) . . ?
N5 Co1 N15 99.45(10) . . ?
N1 Co1 N15 93.77(10) . . ?
N4 N5 N6 119.2(2) . . ?
N4 N5 Co1 121.05(19) . . ?
N6 N5 Co1 119.72(17) . . ?
N5 N6 C3 106.0(2) . . ?
C3 N7 C4 107.0(2) . . ?
C3 N7 Co1 109.47(19) . . ?
C4 N7 Co1 142.81(19) . . ?
C3 N8 C5 107.8(2) . . ?
C3 N8 H8 126.1 . . ?
C5 N8 H8 126.1 . . ?
C1 N1 C2 103.5(2) . . ?
C1 N1 Co1 146.1(2) . . ?
C2 N1 Co1 110.3(2) . . ?
N5 N4 C2 107.2(2) . . ?
C1 N2 N3 112.0(3) . . ?
C1 N2 H2 124.0 . . ?
N3 N2 H2 124.0 . . ?
C2 N3 N2 101.6(3) . . ?
N12 N13 N14 119.0(2) . . ?
N12 N13 Co1 121.3(2) . . ?
N14 N13 Co1 119.73(19) . . ?
C12 N15 C13 106.0(2) . . ?
C12 N15 Co1 110.50(19) . . ?
C13 N15 Co1 143.5(2) . . ?
C11 N9 N10 107.6(2) . . ?
C11 N9 Co1 112.4(2) . . ?
N10 N9 Co1 140.0(2) . . ?
C12 N16 C14 106.7(3) . . ?
C12 N16 H16 126.6 . . ?
C14 N16 H16 126.6 . . ?
N13 N12 C11 106.7(2) . . ?
C15 C14 N16 132.0(3) . . ?
C15 C14 C13 121.3(3) . . ?
N16 C14 C13 106.7(3) . . ?
N13 N14 C12 106.7(2) . . ?
C11 N11 C10 100.4(3) . . ?
C6 C5 N8 132.1(3) . . ?
C6 C5 C4 121.2(3) . . ?
N8 C5 C4 106.6(2) . . ?
N3 C2 N1 113.8(3) . . ?
N3 C2 N4 125.4(3) . . ?
N1 C2 N4 120.8(3) . . ?
C9 C4 N7 132.1(3) . . ?
C9 C4 C5 120.8(3) . . ?
N7 C4 C5 107.2(2) . . ?
N8 C3 N7 111.4(2) . . ?
N8 C3 N6 125.0(3) . . ?
N7 C3 N6 123.5(3) . . ?
C7 C6 C5 117.4(3) . . ?
C7 C6 H6 121.3 . . ?
C5 C6 H6 121.3 . . ?
N2 C1 N1 109.1(3) . . ?
N2 C1 H1 125.5 . . ?
N1 C1 H1 125.5 . . ?
C9 C8 C7 121.4(3) . . ?
C9 C8 H8A 119.3 . . ?
C7 C8 H8A 119.3 . . ?
C8 C9 C4 117.5(3) . . ?
C8 C9 H9 121.3 . . ?
C4 C9 H9 121.3 . . ?
C6 C7 C8 121.7(3) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
N9 C11 N11 113.4(3) . . ?
N9 C11 N12 119.8(3) . . ?
N11 C11 N12 126.8(3) . . ?
C10 N10 N9 102.7(3) . . ?
N15 C12 N16 112.9(3) . . ?
N15 C12 N14 122.3(3) . . ?
N16 C12 N14 124.8(3) . . ?
C18 C13 C14 121.5(3) . . ?
C18 C13 N15 130.7(3) . . ?
C14 C13 N15 107.7(3) . . ?
C13 C18 C17 116.9(3) . . ?
C13 C18 H18 121.5 . . ?
C17 C18 H18 121.5 . . ?
C16 C15 C14 117.1(3) . . ?
C16 C15 H15 121.4 . . ?
C14 C15 H15 121.4 . . ?
C15 C16 C17 121.7(3) . . ?
C15 C16 H16A 119.2 . . ?
C17 C16 H16A 119.2 . . ?
C18 C17 C16 121.4(4) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
N10 C10 N11 115.9(3) . . ?
N10 C10 H10 122.1 . . ?
N11 C10 H10 122.1 . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.054
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1422672'
_audit_update_record             
;
2015-09-05 deposited with the CCDC.
2015-12-28 downloaded from the CCDC.
;
_audit_creation_date             2015-07-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C10 H7 Cu N9 S, H2 O'
_chemical_formula_sum            'C10 H9 Cu N9 O S'
_chemical_formula_weight         366.87
_chemical_melting_point          ?
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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.061(3)
_cell_length_b                   19.716(8)
_cell_length_c                   10.302(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.146(15)
_cell_angle_gamma                90.00
_cell_volume                     1377.6(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4501
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.65
_cell_measurement_theta_min      2.30
_exptl_absorpt_coefficient_mu    1.754
_exptl_absorpt_correction_T_max  0.839
_exptl_absorpt_correction_T_min  0.777
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.0455 before and 0.0307 after correction.
The Ratio of minimum to maximum transmission is 0.8122.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.769
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             740.0
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14361
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.07
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1765
_reflns_number_total             2431
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v7.34A (Bruker, 200?)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.34A (Bruker, 200?)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.749
_refine_diff_density_rms         0.148
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2376
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0468
_refine_ls_restrained_S_all      1.142
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0943P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1613
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N9(H9), C11(H11), C5(H5), C8(H8), C6(H6), C7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cu1 Cu 0.13967(8) 0.08141(3) 0.96882(5) 0.0370(3) Uani 1 d . . .
N8 N 0.2643(5) -0.00545(18) 1.0319(3) 0.0375(9) Uani 1 d . . .
N6 N 0.2458(5) 0.09772(19) 1.1690(4) 0.0358(8) Uani 1 d . . .
N7 N 0.3428(5) 0.0498(2) 1.2472(3) 0.0392(9) Uani 1 d . . .
N4 N 0.0521(5) 0.17413(19) 0.9859(3) 0.0398(9) Uani 1 d . . .
N2 N -0.0278(6) 0.27780(19) 1.0022(4) 0.0475(10) Uani 1 d . . .
H2 H -0.0774 0.3173 0.9794 0.057 Uiso 1 calc . . R
N9 N 0.4489(5) -0.0614(2) 1.2101(4) 0.0403(9) Uani 1 d . . .
H9 H 0.5128 -0.0702 1.2924 0.048 Uiso 1 calc . . R
N1 N 0.0742(6) 0.26007(19) 1.1315(4) 0.0472(10) Uani 1 d . . .
N5 N 0.2245(5) 0.15527(18) 1.2214(4) 0.0404(9) Uani 1 d . . .
C11 C -0.0406(7) 0.2275(2) 0.9178(5) 0.0433(11) Uani 1 d . . .
H11 H -0.1039 0.2287 0.8257 0.052 Uiso 1 calc . . R
C1 C 0.1161(6) 0.1968(2) 1.1148(4) 0.0396(10) Uani 1 d . . .
C4 C 0.3133(7) -0.0679(2) 0.9869(5) 0.0397(11) Uani 1 d . . .
C2 C 0.3502(6) -0.0038(2) 1.1647(4) 0.0391(10) Uani 1 d . . .
C3 C 0.4285(7) -0.1041(2) 1.0989(5) 0.0406(11) Uani 1 d . . .
C5 C 0.2616(7) -0.0958(2) 0.8591(5) 0.0447(12) Uani 1 d . . .
H5 H 0.1864 -0.0720 0.7846 0.054 Uiso 1 calc . . R
C8 C 0.4952(7) -0.1683(2) 1.0874(5) 0.0498(13) Uani 1 d . . .
H8 H 0.5725 -0.1917 1.1617 0.060 Uiso 1 calc . . R
C6 C 0.3268(7) -0.1610(2) 0.8471(5) 0.0515(13) Uani 1 d . . .
H6 H 0.2934 -0.1816 0.7625 0.062 Uiso 1 calc . . R
C7 C 0.4413(8) -0.1971(3) 0.9579(5) 0.0522(13) Uani 1 d . . .
H7 H 0.4824 -0.2408 0.9457 0.063 Uiso 1 calc . . R
N10 N 0.0386(7) 0.0710(2) 0.7770(4) 0.0488(11) Uani 1 d . . .
C9 C -0.0343(8) 0.0811(2) 0.6665(6) 0.0428(12) Uani 1 d . . .
S1 S -0.1416(2) 0.09403(10) 0.50741(15) 0.0727(5) Uani 1 d . . .
O1 O 0.6579(5) 0.91278(17) 0.4812(3) 0.0471(9) Uani 1 d . . .
H1A H 0.7825 0.9162 0.4991 0.071 Uiso 1 d . . G
H1B H 0.6190 0.9322 0.5430 0.071 Uiso 1 d . . G


_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 N8 1.952(4) . ?
Cu1 N6 2.014(4) . ?
Cu1 N4 1.953(4) . ?
Cu1 N10 1.916(4) . ?
N8 C4 1.392(6) . ?
N8 C2 1.334(6) . ?
N6 N7 1.305(5) . ?
N6 N5 1.283(5) . ?
N7 C2 1.368(6) . ?
N4 C11 1.331(5) . ?
N4 C1 1.354(5) . ?
N2 H2 0.8600 . ?
N2 N1 1.372(5) . ?
N2 C11 1.305(6) . ?
N9 H9 0.8600 . ?
N9 C2 1.345(6) . ?
N9 C3 1.396(6) . ?
N1 C1 1.305(6) . ?
N5 C1 1.413(5) . ?
C11 H11 0.9300 . ?
C4 C3 1.408(7) . ?
C4 C5 1.380(7) . ?
C3 C8 1.367(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(6) . ?
C8 H8 0.9300 . ?
C8 C7 1.401(7) . ?
C6 H6 0.9300 . ?
C6 C7 1.396(7) . ?
C7 H7 0.9300 . ?
N10 C9 1.129(7) . ?
C9 S1 1.624(6) . ?
O1 H1A 0.8500 . ?
O1 H1B 0.8500 . ?

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
N8 Cu1 N6 78.14(15) . . ?
N8 Cu1 N4 156.30(15) . . ?
N4 Cu1 N6 78.19(15) . . ?
N10 Cu1 N8 104.67(16) . . ?
N10 Cu1 N6 176.97(16) . . ?
N10 Cu1 N4 99.02(16) . . ?
C4 N8 Cu1 142.7(3) . . ?
C2 N8 Cu1 110.8(3) . . ?
C2 N8 C4 106.2(4) . . ?
N7 N6 Cu1 119.9(3) . . ?
N5 N6 Cu1 121.2(3) . . ?
N5 N6 N7 118.8(4) . . ?
N6 N7 C2 106.2(3) . . ?
C11 N4 Cu1 144.5(3) . . ?
C11 N4 C1 103.7(4) . . ?
C1 N4 Cu1 111.7(3) . . ?
N1 N2 H2 124.0 . . ?
C11 N2 H2 124.0 . . ?
C11 N2 N1 111.9(4) . . ?
C2 N9 H9 126.3 . . ?
C2 N9 C3 107.3(4) . . ?
C3 N9 H9 126.3 . . ?
C1 N1 N2 101.1(4) . . ?
N6 N5 C1 106.7(4) . . ?
N4 C11 H11 125.8 . . ?
N2 C11 N4 108.5(4) . . ?
N2 C11 H11 125.8 . . ?
N4 C1 N5 122.2(4) . . ?
N1 C1 N4 114.8(4) . . ?
N1 C1 N5 123.0(4) . . ?
N8 C4 C3 108.4(5) . . ?
C5 C4 N8 130.3(5) . . ?
C5 C4 C3 121.3(5) . . ?
N8 C2 N7 124.8(4) . . ?
N8 C2 N9 112.4(4) . . ?
N9 C2 N7 122.8(4) . . ?
N9 C3 C4 105.7(4) . . ?
C8 C3 N9 132.1(5) . . ?
C8 C3 C4 122.2(5) . . ?
C4 C5 H5 121.6 . . ?
C4 C5 C6 116.8(5) . . ?
C6 C5 H5 121.6 . . ?
C3 C8 H8 121.7 . . ?
C3 C8 C7 116.7(5) . . ?
C7 C8 H8 121.7 . . ?
C5 C6 H6 118.9 . . ?
C5 C6 C7 122.1(5) . . ?
C7 C6 H6 118.9 . . ?
C8 C7 H7 119.5 . . ?
C6 C7 C8 121.0(5) . . ?
C6 C7 H7 119.5 . . ?
C9 N10 Cu1 162.9(4) . . ?
N10 C9 S1 178.8(5) . . ?
H1A O1 H1B 109.4 . . ?

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
Cu1 N8 C4 C3 173.1(3) . . . . ?
Cu1 N8 C4 C5 -9.0(8) . . . . ?
Cu1 N8 C2 N7 3.5(5) . . . . ?
Cu1 N8 C2 N9 -175.8(3) . . . . ?
Cu1 N6 N7 C2 0.9(4) . . . . ?
Cu1 N6 N5 C1 1.6(4) . . . . ?
Cu1 N4 C11 N2 -174.0(4) . . . . ?
Cu1 N4 C1 N1 175.5(3) . . . . ?
Cu1 N4 C1 N5 -2.9(5) . . . . ?
Cu1 N10 C9 S1 -135(25) . . . . ?
N8 Cu1 N6 N7 0.6(3) . . . . ?
N8 Cu1 N6 N5 178.7(3) . . . . ?
N8 Cu1 N4 C11 -179.8(4) . . . . ?
N8 Cu1 N4 C1 5.5(5) . . . . ?
N8 Cu1 N10 C9 -178.3(15) . . . . ?
N8 C4 C3 N9 -0.9(5) . . . . ?
N8 C4 C3 C8 178.3(4) . . . . ?
N8 C4 C5 C6 -177.1(4) . . . . ?
N6 Cu1 N8 C4 -173.5(5) . . . . ?
N6 Cu1 N8 C2 -1.9(3) . . . . ?
N6 Cu1 N4 C11 177.2(5) . . . . ?
N6 Cu1 N4 C1 2.6(3) . . . . ?
N6 Cu1 N10 C9 -21(4) . . . . ?
N6 N7 C2 N8 -2.9(5) . . . . ?
N6 N7 C2 N9 176.3(4) . . . . ?
N6 N5 C1 N4 0.9(5) . . . . ?
N6 N5 C1 N1 -177.3(4) . . . . ?
N7 N6 N5 C1 179.7(3) . . . . ?
N4 Cu1 N8 C4 -176.4(4) . . . . ?
N4 Cu1 N8 C2 -4.9(5) . . . . ?
N4 Cu1 N6 N7 179.4(3) . . . . ?
N4 Cu1 N6 N5 -2.5(3) . . . . ?
N4 Cu1 N10 C9 2.4(15) . . . . ?
N2 N1 C1 N4 1.1(5) . . . . ?
N2 N1 C1 N5 179.5(4) . . . . ?
N9 C3 C8 C7 178.3(4) . . . . ?
N1 N2 C11 N4 -0.2(5) . . . . ?
N5 N6 N7 C2 -177.3(3) . . . . ?
C11 N4 C1 N1 -1.3(5) . . . . ?
C11 N4 C1 N5 -179.7(4) . . . . ?
C11 N2 N1 C1 -0.5(5) . . . . ?
C1 N4 C11 N2 0.9(5) . . . . ?
C4 N8 C2 N7 178.2(4) . . . . ?
C4 N8 C2 N9 -1.1(5) . . . . ?
C4 C3 C8 C7 -0.7(6) . . . . ?
C4 C5 C6 C7 -0.6(7) . . . . ?
C2 N8 C4 C3 1.3(5) . . . . ?
C2 N8 C4 C5 179.2(4) . . . . ?
C2 N9 C3 C4 0.3(5) . . . . ?
C2 N9 C3 C8 -178.8(4) . . . . ?
C3 N9 C2 N8 0.6(5) . . . . ?
C3 N9 C2 N7 -178.8(4) . . . . ?
C3 C4 C5 C6 0.5(7) . . . . ?
C3 C8 C7 C6 0.6(7) . . . . ?
C5 C4 C3 N9 -179.1(4) . . . . ?
C5 C4 C3 C8 0.1(7) . . . . ?
C5 C6 C7 C8 0.1(7) . . . . ?
N10 Cu1 N8 C4 5.3(5) . . . . ?
N10 Cu1 N8 C2 176.9(3) . . . . ?
N10 Cu1 N6 N7 -157(3) . . . . ?
N10 Cu1 N6 N5 21(3) . . . . ?
N10 Cu1 N4 C11 -1.6(5) . . . . ?
N10 Cu1 N4 C1 -176.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1422673'
_audit_update_record             
;
2015-09-05 deposited with the CCDC.
2015-12-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H20 Cd2 Cl4 N16 O2'
_chemical_formula_weight         859.12

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   8.3541(4)
_cell_length_b                   17.9999(9)
_cell_length_c                   10.0103(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.893(2)
_cell_angle_gamma                90.00
_cell_volume                     1396.72(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      27.61

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    2.043
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840.0
_exptl_absorpt_coefficient_mu    1.957
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.753
_exptl_absorpt_correction_T_max  0.839
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean none
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            22737
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         27.61
_reflns_number_total             3237
_reflns_number_gt                2802
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0261P)²+0.2901P] 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     SHELXL
_refine_ls_extinction_coef       0.0010(1)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3236
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0207
_refine_ls_wR_factor_ref         0.0510
_refine_ls_wR_factor_gt          0.0483
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.042
_refine_ls_shift/su_mean         0.006

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
Cd1 Cd 0.394686(19) 0.469376(8) 0.625734(14) 0.03090(6) Uani 1 1 d . . .
Cl1 Cl 0.43234(7) 0.59424(3) 0.51545(5) 0.03607(12) Uani 1 1 d . . .
Cl2 Cl 0.12707(7) 0.40171(3) 0.48460(6) 0.03917(13) Uani 1 1 d . . .
N4 N 0.4839(2) 0.39102(9) 0.86306(17) 0.0295(4) Uani 1 1 d . . .
N6 N 0.6276(2) 0.48385(9) 0.83453(17) 0.0293(4) Uani 1 1 d . . .
N7 N 0.8402(2) 0.54144(9) 1.04205(17) 0.0283(4) Uani 1 1 d . . .
N5 N 0.6074(2) 0.43522(9) 0.92780(17) 0.0286(4) Uani 1 1 d . . .
N8 N 0.8098(2) 0.58293(10) 0.82981(18) 0.0337(4) Uani 1 1 d . . .
C4 C 0.9529(3) 0.60100(11) 1.0638(2) 0.0305(4) Uani 1 1 d . . .
C5 C 0.9337(3) 0.62760(12) 0.9281(2) 0.0326(5) Uani 1 1 d . . .
C3 C 0.7535(3) 0.53264(10) 0.9005(2) 0.0277(4) Uani 1 1 d . . .
C2 C 0.4552(3) 0.34092(11) 0.9581(2) 0.0289(4) Uani 1 1 d . . .
C1 C 0.4501(3) 0.28902(13) 1.1425(3) 0.0408(5) Uani 1 1 d . . .
N3 N 0.5230(2) 0.34592(10) 1.10394(18) 0.0347(4) Uani 1 1 d . . .
N1 N 0.3476(3) 0.28522(10) 0.9061(2) 0.0400(4) Uani 1 1 d . . .
N2 N 0.3481(3) 0.25292(10) 1.0281(2) 0.0437(5) Uani 1 1 d . . .
C9 C 1.0644(3) 0.63396(13) 1.1875(2) 0.0402(5) Uani 1 1 d . . .
C6 C 1.0232(3) 0.68889(13) 0.9101(3) 0.0436(5) Uani 1 1 d . . .
C7 C 1.1338(3) 0.72236(14) 1.0344(3) 0.0486(6) Uani 1 1 d . . .
C8 C 1.1546(3) 0.69508(14) 1.1698(3) 0.0476(6) Uani 1 1 d . . .
O1 O 0.23820(19) 0.54034(8) 0.74265(15) 0.0336(3) Uani 1 1 d . . .
H1 H 0.4663 0.2751 1.2373 0.048(7) Uiso 1 1 d R . .
H2 H 0.2821 0.2160 1.0237 0.063(9) Uiso 1 1 d R . .
H3 H 0.8199 0.5171 1.1034 0.035(6) Uiso 1 1 d R . .
H4 H 0.7795 0.5848 0.7510 0.032(6) Uiso 1 1 d R . .
H5 H 1.0058 0.7070 0.8163 0.042(6) Uiso 1 1 d R . .
H7 H 1.2286 0.7181 1.2504 0.046(7) Uiso 1 1 d R . .
H6 H 1.1947 0.7612 1.0266 0.055(8) Uiso 1 1 d R . .
H8 H 1.0778 0.6157 1.2775 0.043(7) Uiso 1 1 d R . .
H9 H 0.1497 0.5561 0.6805 0.053(8) Uiso 1 1 d R . .
H10 H 0.3029 0.5761 0.7864 0.051(8) Uiso 1 1 d R . .


_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 N6 2.2782(16) . ?
Cd1 O1 2.4190(14) . ?
Cd1 Cl2 2.4743(5) . ?
Cd1 Cl1 2.5746(5) . ?
Cd1 N4 2.6207(16) . ?
Cd1 Cl1 2.6306(6) 3_666 ?
Cl1 Cd1 2.6306(6) 3_666 ?
N4 N5 1.272(2) . ?
N4 C2 1.395(3) . ?
N6 N5 1.336(2) . ?
N6 C3 1.340(3) . ?
N7 C3 1.339(2) . ?
N7 C4 1.390(3) . ?
N7 H3 0.8220 . ?
N8 C3 1.338(3) . ?
N8 C5 1.388(3) . ?
N8 H4 0.7340 . ?
C4 C9 1.375(3) . ?
C4 C5 1.392(3) . ?
C5 C6 1.382(3) . ?
C2 N1 1.317(3) . ?
C2 N3 1.358(3) . ?
C1 N2 1.316(3) . ?
C1 N3 1.321(3) . ?
C1 H1 0.9407 . ?
N1 N2 1.352(3) . ?
N2 H2 0.8545 . ?
C9 C8 1.382(4) . ?
C9 H8 0.9264 . ?
C6 C7 1.381(3) . ?
C6 H5 0.9528 . ?
C7 C8 1.390(4) . ?
C7 H6 0.8851 . ?
C8 H7 0.9133 . ?
O1 H9 0.8196 . ?
O1 H10 0.8490 . ?

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
N6 Cd1 O1 85.79(6) . . ?
N6 Cd1 Cl2 149.43(5) . . ?
O1 Cd1 Cl2 90.00(4) . . ?
N6 Cd1 Cl1 95.42(4) . . ?
O1 Cd1 Cl1 85.47(4) . . ?
Cl2 Cd1 Cl1 114.440(18) . . ?
N6 Cd1 N4 51.16(6) . . ?
O1 Cd1 N4 82.41(5) . . ?
Cl2 Cd1 N4 98.27(4) . . ?
Cl1 Cd1 N4 145.04(4) . . ?
N6 Cd1 Cl1 95.18(5) . 3_666 ?
O1 Cd1 Cl1 173.75(4) . 3_666 ?
Cl2 Cd1 Cl1 92.256(19) . 3_666 ?
Cl1 Cd1 Cl1 88.295(17) . 3_666 ?
N4 Cd1 Cl1 103.01(4) . 3_666 ?
Cd1 Cl1 Cd1 91.705(17) . 3_666 ?
N5 N4 C2 111.71(16) . . ?
N5 N4 Cd1 91.59(11) . . ?
C2 N4 Cd1 154.54(13) . . ?
N5 N6 C3 111.45(16) . . ?
N5 N6 Cd1 106.20(12) . . ?
C3 N6 Cd1 140.54(13) . . ?
C3 N7 C4 108.94(17) . . ?
C3 N7 H3 123.2 . . ?
C4 N7 H3 127.7 . . ?
N4 N5 N6 110.10(16) . . ?
C3 N8 C5 109.47(16) . . ?
C3 N8 H4 123.5 . . ?
C5 N8 H4 127.0 . . ?
C9 C4 N7 131.7(2) . . ?
C9 C4 C5 121.5(2) . . ?
N7 C4 C5 106.71(18) . . ?
C6 C5 N8 131.8(2) . . ?
C6 C5 C4 122.0(2) . . ?
N8 C5 C4 106.07(18) . . ?
N8 C3 N7 108.78(17) . . ?
N8 C3 N6 123.30(17) . . ?
N7 C3 N6 127.90(18) . . ?
N1 C2 N3 115.18(19) . . ?
N1 C2 N4 119.19(18) . . ?
N3 C2 N4 125.55(18) . . ?
N2 C1 N3 110.4(2) . . ?
N2 C1 H1 123.3 . . ?
N3 C1 H1 126.3 . . ?
C1 N3 C2 102.11(18) . . ?
C2 N1 N2 101.41(18) . . ?
C1 N2 N1 110.94(19) . . ?
C1 N2 H2 128.7 . . ?
N1 N2 H2 120.2 . . ?
C4 C9 C8 116.5(2) . . ?
C4 C9 H8 121.2 . . ?
C8 C9 H8 122.3 . . ?
C7 C6 C5 116.4(2) . . ?
C7 C6 H5 122.9 . . ?
C5 C6 H5 120.7 . . ?
C6 C7 C8 121.5(2) . . ?
C6 C7 H6 118.6 . . ?
C8 C7 H6 119.9 . . ?
C9 C8 C7 122.0(2) . . ?
C9 C8 H7 118.0 . . ?
C7 C8 H7 119.9 . . ?
Cd1 O1 H9 108.2 . . ?
Cd1 O1 H10 107.1 . . ?
H9 O1 H10 110.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.61
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.067
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1428456'
_audit_update_record             
;
2015-09-29 deposited with the CCDC.
2015-12-28 downloaded from the CCDC.
;
_audit_creation_date             2015-09-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        'Nickel complex'
_chemical_formula_moiety         'C40 H40 N36 Ni3, C3 O, O2, 2(O)'
_chemical_formula_sum            'C43 H40 N36 Ni3 O5'
_chemical_formula_weight         1317.18
_chemical_melting_point          ?
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'
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'

_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.
;
_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'
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                   11.7945(11)
_cell_length_b                   15.2176(14)
_cell_length_c                   19.0428(18)
_cell_angle_alpha                90
_cell_angle_beta                 105.480(6)
_cell_angle_gamma                90
_cell_volume                     3293.9(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4165
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   0.914
_shelx_estimated_absorpt_T_min   0.838
_exptl_absorpt_coefficient_mu    0.917
_exptl_absorpt_correction_T_max  0.912
_exptl_absorpt_correction_T_min  0.832
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1348
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_av_unetI/netI     0.0902
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            26830
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.983
_diffrn_reflns_theta_min         1.738
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3864
_reflns_number_total             7938
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.34A (Bruker, 200?)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.34A (Bruker, 200?)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.835
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         7519
_refine_ls_number_restraints     49
_refine_ls_R_factor_all          0.1348
_refine_ls_R_factor_gt           0.0654
_refine_ls_restrained_S_all      0.979
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1190P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1772
_refine_ls_wR_factor_ref         0.2130
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
2. Restrained distances
 C22-C21
 1.4 with sigma of 0.02
3. Rigid bond restraints
 O1, C22, C23
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
O1 \\sim C21 \\sim C22 \\sim C23: within 2A with sigma of 0.02 and sigma for
terminal atoms of 0.04
Uanis(O1W) \\sim Ueq, Uanis(O1X) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C22) \\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(O1) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
5. Others
 Fixed Sof: O1(0.5) C21(0.5) C22(0.5) C23(0.5) O1W(0.5) O1X(0.5)
6.a Secondary CH2 refined with riding coordinates:
 N17(H17A,H17B), N18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B)
6.b Aromatic/amide H refined with riding coordinates:
 N7(H7), N10(H10), C1(H1), C5(H5), C6(H6), C7(H7A), C8(H8), C12(H12), C13(H13),
  C14(H14), C15(H15), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.35619(4) 0.39590(3) 0.18730(2) 0.04321(12) Uani 1 1 d . . . . .
Ni2 Ni 0.5000 0.5000 0.5000 0.0618(2) Uani 1 2 d S T P . .
N1 N 0.3669(2) 0.25948(19) 0.18854(14) 0.0492(8) Uani 1 1 d . . . . .
N2 N 0.3843(3) 0.1171(2) 0.18897(17) 0.0612(9) Uani 1 1 d . . . . .
N3 N 0.4114(3) 0.1428(2) 0.12800(18) 0.0664(9) Uani 1 1 d . . . . .
N4 N 0.4250(3) 0.28468(19) 0.07771(16) 0.0571(8) Uani 1 1 d . . . . .
N5 N 0.4189(3) 0.36368(19) 0.09928(15) 0.0498(8) Uani 1 1 d . . . . .
N6 N 0.4402(3) 0.42658(19) 0.05642(15) 0.0574(8) Uani 1 1 d . . . . .
N7 N 0.4486(3) 0.58238(19) 0.05909(17) 0.0611(9) Uani 1 1 d . . . . .
H7 H 0.4676 0.5895 0.0189 0.073 Uiso 1 1 calc R . . . .
N8 N 0.3972(3) 0.51504(17) 0.15008(15) 0.0467(7) Uani 1 1 d . . . . .
N9 N 0.1792(3) 0.40036(17) 0.12773(15) 0.0483(8) Uani 1 1 d . . . . .
N10 N 0.0011(3) 0.4448(2) 0.13242(18) 0.0618(9) Uani 1 1 d . . . . .
H10 H -0.0533 0.4666 0.1496 0.074 Uiso 1 1 calc R . . . .
N11 N 0.1579(3) 0.46508(19) 0.23894(15) 0.0508(8) Uani 1 1 d . . . . .
N12 N 0.2703(3) 0.44369(18) 0.26044(14) 0.0458(7) Uani 1 1 d . . . . .
N13 N 0.3244(3) 0.46360(19) 0.32633(15) 0.0510(8) Uani 1 1 d . . . . .
N14 N 0.4858(3) 0.40257(19) 0.28634(15) 0.0529(8) Uani 1 1 d . . . . .
N15 N 0.6201(3) 0.4066(2) 0.39491(18) 0.0741(11) Uani 1 1 d . . . . .
N16 N 0.5172(3) 0.4408(2) 0.40316(16) 0.0629(9) Uani 1 1 d . . . . .
N17 N 0.4405(4) 0.6167(2) 0.44347(19) 0.0826(12) Uani 1 1 d . . . . .
H17A H 0.3850 0.6051 0.4027 0.099 Uiso 1 1 calc R . . . .
H17B H 0.4104 0.6524 0.4709 0.099 Uiso 1 1 calc R . . . .
N18 N 0.6644(3) 0.5589(3) 0.51189(18) 0.0829(12) Uani 1 1 d . . . . .
H18A H 0.7070 0.5550 0.5580 0.100 Uiso 1 1 calc R . . . .
H18B H 0.7029 0.5315 0.4840 0.100 Uiso 1 1 calc R . . . .
C1 C 0.3600(3) 0.1859(2) 0.2246(2) 0.0567(10) Uani 1 1 d . . . . .
H1 H 0.3407 0.1832 0.2688 0.068 Uiso 1 1 calc R . . . .
C2 C 0.4018(3) 0.2300(2) 0.12989(19) 0.0502(9) Uani 1 1 d . . . . .
C3 C 0.4286(3) 0.5049(2) 0.0889(2) 0.0523(10) Uani 1 1 d . . . . .
C4 C 0.4325(3) 0.6481(2) 0.1064(2) 0.0569(10) Uani 1 1 d . . . . .
C5 C 0.4424(4) 0.7381(3) 0.1039(3) 0.0799(14) Uani 1 1 d . . . . .
H5 H 0.4638 0.7663 0.0660 0.096 Uiso 1 1 calc R . . . .
C6 C 0.4193(4) 0.7836(3) 0.1600(3) 0.0896(15) Uani 1 1 d . . . . .
H6 H 0.4219 0.8447 0.1592 0.108 Uiso 1 1 calc R . . . .
C7 C 0.3921(5) 0.7420(3) 0.2182(3) 0.0874(15) Uani 1 1 d . . . . .
H7A H 0.3805 0.7756 0.2565 0.105 Uiso 1 1 calc R . . . .
C8 C 0.3819(3) 0.6526(3) 0.2205(2) 0.0624(11) Uani 1 1 d . . . . .
H8 H 0.3632 0.6247 0.2593 0.075 Uiso 1 1 calc R . . . .
C9 C 0.4008(3) 0.6052(2) 0.1624(2) 0.0503(9) Uani 1 1 d . . . . .
C10 C 0.1162(3) 0.4373(2) 0.16804(19) 0.0493(9) Uani 1 1 d . . . . .
C11 C -0.0131(4) 0.4107(2) 0.0627(2) 0.0624(12) Uani 1 1 d . . . . .
C12 C -0.1094(4) 0.4014(3) 0.0044(3) 0.0809(15) Uani 1 1 d . . . . .
H12 H -0.1833 0.4205 0.0066 0.097 Uiso 1 1 calc R . . . .
C13 C -0.0938(5) 0.3634(3) -0.0567(3) 0.0910(16) Uani 1 1 d . . . . .
H13 H -0.1578 0.3572 -0.0973 0.109 Uiso 1 1 calc R . . . .
C14 C 0.0156(4) 0.3337(3) -0.0597(2) 0.0832(15) Uani 1 1 d . . . . .
H14 H 0.0235 0.3064 -0.1018 0.100 Uiso 1 1 calc R . . . .
C15 C 0.1132(4) 0.3437(3) -0.0014(2) 0.0695(12) Uani 1 1 d . . . . .
H15 H 0.1867 0.3244 -0.0041 0.083 Uiso 1 1 calc R . . . .
C16 C 0.0995(3) 0.3828(2) 0.06109(19) 0.0513(10) Uani 1 1 d . . . . .
C17 C 0.4408(3) 0.4364(2) 0.33786(18) 0.0528(10) Uani 1 1 d . . . . .
C18 C 0.5959(4) 0.3849(3) 0.3246(2) 0.0695(12) Uani 1 1 d . . . . .
H18 H 0.6511 0.3596 0.3040 0.083 Uiso 1 1 calc R . . . .
C19 C 0.5418(6) 0.6577(4) 0.4265(3) 0.111(2) Uani 1 1 d . . . . .
H19A H 0.5244 0.7188 0.4137 0.133 Uiso 1 1 calc R . . . .
H19B H 0.5581 0.6283 0.3850 0.133 Uiso 1 1 calc R . . . .
C20 C 0.6468(6) 0.6520(4) 0.4904(3) 0.119(2) Uani 1 1 d . . . . .
H20A H 0.7156 0.6744 0.4776 0.142 Uiso 1 1 calc R . . . .
H20B H 0.6345 0.6867 0.5304 0.142 Uiso 1 1 calc R . . . .
O1 O 0.8634(5) 0.5029(4) 0.2309(3) 0.0768(18) Uani 0.5 1 d . U . A -1
C21 C 0.7666(12) 0.5609(10) 0.2216(6) 0.138(4) Uani 0.5 1 d D U . A -1
C22 C 0.7621(15) 0.6100(12) 0.1601(8) 0.200(7) Uani 0.5 1 d D U . A -1
C23 C 0.7448(12) 0.6080(9) 0.2777(8) 0.139(5) Uani 0.5 1 d . U . A -1
O1W O 0.6451(8) 0.9241(6) 0.0277(4) 0.135(3) Uani 0.5 1 d . U . B -1
O1X O 0.6453(10) 0.8507(10) 0.0530(7) 0.200(5) Uani 0.5 1 d . U . B -1
O2W O 0.9650(8) 0.4767(4) 0.3804(4) 0.266(3) Uani 1 1 d . . . C -1


_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 N1 2.080(3) . ?
Ni1 N5 2.064(3) . ?
Ni1 N8 2.051(3) . ?
Ni1 N9 2.094(3) . ?
Ni1 N12 2.061(3) . ?
Ni1 N14 2.090(3) . ?
Ni2 N16 2.110(3) 3_666 ?
Ni2 N16 2.110(3) . ?
Ni2 N17 2.098(3) . ?
Ni2 N17 2.098(3) 3_666 ?
Ni2 N18 2.093(4) . ?
Ni2 N18 2.093(4) 3_666 ?
N1 C1 1.327(4) . ?
N1 C2 1.365(5) . ?
N2 N3 1.343(5) . ?
N2 C1 1.320(5) . ?
N3 C2 1.332(5) . ?
N4 N5 1.279(4) . ?
N4 C2 1.379(5) . ?
N5 N6 1.325(4) . ?
N6 C3 1.367(4) . ?
N7 C3 1.356(4) . ?
N7 C4 1.392(5) . ?
N8 C3 1.323(5) . ?
N8 C9 1.391(4) . ?
N9 C10 1.328(5) . ?
N9 C16 1.389(4) . ?
N10 C10 1.351(5) . ?
N10 C11 1.392(5) . ?
N11 N12 1.320(4) . ?
N11 C10 1.374(4) . ?
N12 N13 1.283(4) . ?
N13 C17 1.394(5) . ?
N14 C17 1.337(5) . ?
N14 C18 1.335(5) . ?
N15 N16 1.368(5) . ?
N15 C18 1.333(5) . ?
N16 C17 1.328(4) . ?
N17 C19 1.458(7) . ?
N18 C20 1.473(6) . ?
C4 C5 1.377(5) . ?
C4 C9 1.384(5) . ?
C5 C6 1.359(7) . ?
C6 C7 1.387(7) . ?
C7 C8 1.369(6) . ?
C8 C9 1.387(5) . ?
C11 C12 1.367(6) . ?
C11 C16 1.403(6) . ?
C12 C13 1.356(7) . ?
C13 C14 1.383(7) . ?
C14 C15 1.378(6) . ?
C15 C16 1.378(5) . ?
C19 C20 1.489(7) . ?
O1 C21 1.417(14) . ?
C21 C22 1.376(14) . ?
C21 C23 1.367(17) . ?
O1W O1X 1.216(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ni1 N9 95.00(11) . . ?
N1 Ni1 N14 90.61(11) . . ?
N5 Ni1 N1 74.82(11) . . ?
N5 Ni1 N9 95.12(11) . . ?
N5 Ni1 N14 114.21(12) . . ?
N8 Ni1 N1 150.14(11) . . ?
N8 Ni1 N5 76.16(11) . . ?
N8 Ni1 N9 94.41(11) . . ?
N8 Ni1 N12 97.19(11) . . ?
N8 Ni1 N14 94.92(11) . . ?
N12 Ni1 N1 112.57(11) . . ?
N12 Ni1 N5 168.54(11) . . ?
N12 Ni1 N9 75.89(11) . . ?
N12 Ni1 N14 75.29(11) . . ?
N14 Ni1 N9 150.57(12) . . ?
N16 Ni2 N16 180.0 3_666 . ?
N17 Ni2 N16 90.56(13) . . ?
N17 Ni2 N16 89.44(13) . 3_666 ?
N17 Ni2 N16 89.44(13) 3_666 . ?
N17 Ni2 N16 90.56(13) 3_666 3_666 ?
N17 Ni2 N17 180.0(2) 3_666 . ?
N18 Ni2 N16 91.44(14) 3_666 . ?
N18 Ni2 N16 91.44(14) . 3_666 ?
N18 Ni2 N16 88.56(14) 3_666 3_666 ?
N18 Ni2 N16 88.56(14) . . ?
N18 Ni2 N17 97.70(16) 3_666 . ?
N18 Ni2 N17 97.70(16) . 3_666 ?
N18 Ni2 N17 82.30(16) . . ?
N18 Ni2 N17 82.30(16) 3_666 3_666 ?
N18 Ni2 N18 180.0 . 3_666 ?
C1 N1 Ni1 146.8(3) . . ?
C1 N1 C2 102.6(3) . . ?
C2 N1 Ni1 110.5(2) . . ?
C1 N2 N3 110.3(3) . . ?
C2 N3 N2 103.0(3) . . ?
N5 N4 C2 107.3(3) . . ?
N4 N5 Ni1 123.2(2) . . ?
N4 N5 N6 116.4(3) . . ?
N6 N5 Ni1 119.8(2) . . ?
N5 N6 C3 107.1(3) . . ?
C3 N7 C4 106.5(3) . . ?
C3 N8 Ni1 110.4(2) . . ?
C3 N8 C9 105.0(3) . . ?
C9 N8 Ni1 144.4(2) . . ?
C10 N9 Ni1 109.4(2) . . ?
C10 N9 C16 105.2(3) . . ?
C16 N9 Ni1 145.4(3) . . ?
C10 N10 C11 107.2(3) . . ?
N12 N11 C10 107.2(3) . . ?
N11 N12 Ni1 120.8(2) . . ?
N13 N12 Ni1 122.6(2) . . ?
N13 N12 N11 116.2(3) . . ?
N12 N13 C17 107.2(3) . . ?
C17 N14 Ni1 110.1(2) . . ?
C18 N14 Ni1 148.6(3) . . ?
C18 N14 C17 101.2(3) . . ?
C18 N15 N16 104.5(3) . . ?
N15 N16 Ni2 123.9(2) . . ?
C17 N16 Ni2 129.8(3) . . ?
C17 N16 N15 105.9(3) . . ?
C19 N17 Ni2 107.1(3) . . ?
C20 N18 Ni2 108.9(3) . . ?
N2 C1 N1 110.7(3) . . ?
N1 C2 N4 123.5(3) . . ?
N3 C2 N1 113.3(3) . . ?
N3 C2 N4 123.1(3) . . ?
N7 C3 N6 121.3(3) . . ?
N8 C3 N6 125.8(3) . . ?
N8 C3 N7 112.9(3) . . ?
C5 C4 N7 131.7(4) . . ?
C5 C4 C9 122.6(4) . . ?
C9 C4 N7 105.8(3) . . ?
C6 C5 C4 116.3(4) . . ?
C5 C6 C7 122.3(4) . . ?
C8 C7 C6 121.3(4) . . ?
C7 C8 C9 117.3(4) . . ?
C4 C9 N8 109.8(3) . . ?
C4 C9 C8 120.2(3) . . ?
C8 C9 N8 130.0(3) . . ?
N9 C10 N10 112.9(3) . . ?
N9 C10 N11 126.1(3) . . ?
N10 C10 N11 121.1(3) . . ?
N10 C11 C16 105.1(3) . . ?
C12 C11 N10 132.5(4) . . ?
C12 C11 C16 122.4(4) . . ?
C13 C12 C11 117.9(5) . . ?
C12 C13 C14 121.1(4) . . ?
C15 C14 C13 121.3(5) . . ?
C14 C15 C16 118.6(4) . . ?
N9 C16 C11 109.6(3) . . ?
C15 C16 N9 131.6(4) . . ?
C15 C16 C11 118.7(3) . . ?
N14 C17 N13 124.5(3) . . ?
N16 C17 N13 121.7(3) . . ?
N16 C17 N14 113.8(3) . . ?
N15 C18 N14 114.5(4) . . ?
N17 C19 C20 110.3(5) . . ?
N18 C20 C19 108.0(4) . . ?
C22 C21 O1 107.0(12) . . ?
C23 C21 O1 122.8(10) . . ?
C23 C21 C22 114.1(14) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_original_sample_id 1
_olex2_submission_special_instructions 'No special instructions were received'
