# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_xb8999
_database_code_depnum_ccdc_archive 'CCDC 1456495'
_audit_update_record             
;
2016-03-28 deposited with the CCDC.
2016-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H22 N12 Ni O2 S2'
_chemical_formula_weight         657.39

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'
Ni Ni 0.3393 1.1124 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'Pca2(1) '

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

_cell_length_a                   17.199(2)
_cell_length_b                   9.8597(13)
_cell_length_c                   16.463(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2791.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3377
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      24.05

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1352
_exptl_absorpt_coefficient_mu    0.895
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14259
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_sigmaI/netI    0.0521
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         26.09
_reflns_number_total             5424
_reflns_number_gt                4431
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 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)+(0.0631P)²+1.4326P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.08(2)
_refine_ls_number_reflns         5424
_refine_ls_number_parameters     393
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1279
_refine_ls_wR_factor_gt          0.1173
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1262(3) 0.3921(5) 0.5584(3) 0.0368(11) Uani 1 1 d . . .
H1 H 0.1795 0.4075 0.5586 0.044 Uiso 1 1 calc R . .
C2 C 0.0830(3) 0.4512(5) 0.4980(3) 0.0391(11) Uani 1 1 d . . .
H2 H 0.1064 0.5048 0.4584 0.047 Uiso 1 1 calc R . .
C3 C 0.0032(3) 0.4286(5) 0.4977(3) 0.0373(11) Uani 1 1 d . . .
H3 H -0.0278 0.4674 0.4576 0.045 Uiso 1 1 calc R . .
C4 C -0.0298(2) 0.3484(5) 0.5571(3) 0.0343(10) Uani 1 1 d . . .
C5 C 0.0187(3) 0.2930(5) 0.6164(3) 0.0345(10) Uani 1 1 d . . .
H5 H -0.0035 0.2399 0.6569 0.041 Uiso 1 1 calc R . .
C6 C -0.1142(3) 0.3239(5) 0.5606(3) 0.0349(10) Uani 1 1 d . . .
C7 C -0.2276(3) 0.2507(4) 0.5823(3) 0.0335(10) Uani 1 1 d . . .
C8 C -0.2931(3) 0.1684(5) 0.6120(3) 0.0345(10) Uani 1 1 d . . .
C9 C -0.3693(3) 0.2174(5) 0.6057(3) 0.0417(12) Uani 1 1 d . . .
H9 H -0.3791 0.3004 0.5809 0.050 Uiso 1 1 calc R . .
C10 C -0.4287(3) 0.1422(5) 0.6364(4) 0.0476(13) Uani 1 1 d . . .
H10 H -0.4796 0.1739 0.6336 0.057 Uiso 1 1 calc R . .
C11 C -0.4129(3) 0.0183(5) 0.6717(3) 0.0399(11) Uani 1 1 d . . .
H11 H -0.4539 -0.0309 0.6938 0.048 Uiso 1 1 calc R . .
C12 C -0.2821(3) 0.0417(4) 0.6481(3) 0.0354(10) Uani 1 1 d . . .
H12 H -0.2317 0.0087 0.6532 0.042 Uiso 1 1 calc R . .
C13 C 0.2246(3) 0.1037(5) 0.8690(3) 0.0414(12) Uani 1 1 d . . .
H13 H 0.1718 0.0831 0.8689 0.050 Uiso 1 1 calc R . .
C14 C 0.2690(3) 0.0587(5) 0.9325(3) 0.0453(12) Uani 1 1 d . . .
H14 H 0.2459 0.0123 0.9754 0.054 Uiso 1 1 calc R . .
C15 C 0.3474(3) 0.0823(5) 0.9327(3) 0.0430(12) Uani 1 1 d . . .
H15 H 0.3784 0.0511 0.9750 0.052 Uiso 1 1 calc R . .
C16 C 0.3798(3) 0.1543(5) 0.8677(3) 0.0341(10) Uani 1 1 d . . .
C17 C 0.3303(3) 0.1975(5) 0.8067(3) 0.0365(11) Uani 1 1 d . . .
H17 H 0.3519 0.2443 0.7632 0.044 Uiso 1 1 calc R . .
C18 C 0.4634(3) 0.1798(5) 0.8625(3) 0.0350(10) Uani 1 1 d . . .
C19 C 0.5767(3) 0.2550(4) 0.8386(3) 0.0337(10) Uani 1 1 d . . .
C20 C 0.6414(3) 0.3391(5) 0.8096(3) 0.0345(10) Uani 1 1 d . . .
C21 C 0.7174(3) 0.2911(5) 0.8145(3) 0.0458(13) Uani 1 1 d . . .
H21 H 0.7278 0.2074 0.8382 0.055 Uiso 1 1 calc R . .
C22 C 0.7766(3) 0.3689(5) 0.7842(4) 0.0457(13) Uani 1 1 d . . .
H22 H 0.8275 0.3370 0.7854 0.055 Uiso 1 1 calc R . .
C23 C 0.7606(3) 0.4942(5) 0.7520(3) 0.0418(12) Uani 1 1 d . . .
H23 H 0.8015 0.5456 0.7317 0.050 Uiso 1 1 calc R . .
C24 C 0.6306(3) 0.4668(5) 0.7776(3) 0.0355(11) Uani 1 1 d . . .
H24 H 0.5803 0.5013 0.7757 0.043 Uiso 1 1 calc R . .
C25 C 0.0270(3) 0.2290(4) 0.8316(3) 0.0319(11) Uani 1 1 d . . .
C26 C 0.3158(3) 0.2594(4) 0.5899(4) 0.0358(12) Uani 1 1 d . . .
N1 N 0.0964(2) 0.3131(4) 0.6174(3) 0.0347(9) Uani 1 1 d . . .
N2 N -0.1658(2) 0.4078(4) 0.5273(3) 0.0427(10) Uani 1 1 d D . .
N3 N -0.2394(2) 0.3641(4) 0.5408(3) 0.0457(11) Uani 1 1 d . . .
N4 N -0.1509(2) 0.2208(4) 0.5969(3) 0.0363(9) Uani 1 1 d . . .
N5 N -0.3411(2) -0.0343(4) 0.6757(2) 0.0342(9) Uani 1 1 d . . .
N6 N 0.2537(2) 0.1765(4) 0.8063(2) 0.0340(9) Uani 1 1 d . . .
N7 N 0.4998(2) 0.2797(4) 0.8240(3) 0.0357(9) Uani 1 1 d . . .
N8 N 0.5165(2) 0.1007(4) 0.8994(3) 0.0417(10) Uani 1 1 d . . .
H8 H 0.5056 0.0306 0.9283 0.050 Uiso 1 1 calc R . .
N9 N 0.5902(2) 0.1468(4) 0.8850(3) 0.0431(10) Uani 1 1 d . . .
N10 N 0.6892(2) 0.5453(4) 0.7485(2) 0.0360(9) Uani 1 1 d . . .
N11 N 0.0813(2) 0.2306(4) 0.7889(3) 0.0383(10) Uani 1 1 d . . .
N12 N 0.2653(2) 0.2561(4) 0.6346(3) 0.0364(10) Uani 1 1 d . . .
Ni1 Ni 0.17383(3) 0.24397(6) 0.71281(5) 0.03077(15) Uani 1 1 d . . .
S1 S -0.04873(7) 0.22329(14) 0.89104(9) 0.0466(3) Uani 1 1 d . . .
S2 S 0.38834(9) 0.26609(15) 0.52434(9) 0.0540(4) Uani 1 1 d . . .
O2 O 0.9073(4) 0.0374(9) 0.7152(7) 0.180(4) Uani 1 1 d . . .
H2A H 0.9161 -0.0471 0.7200 0.270 Uiso 1 1 d R . .
H2C H 0.9277 0.0795 0.7548 0.270 Uiso 1 1 d R . .
O1 O 0.4411(4) 0.4532(8) 0.6971(6) 0.147(3) Uani 1 1 d . . .
H1A H 0.4368 0.5387 0.6921 0.220 Uiso 1 1 d R . .
H1B H 0.4661 0.4350 0.7402 0.220 Uiso 1 1 d R . .
H2N H -0.164(3) 0.481(4) 0.499(3) 0.068(19) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.346(6) . ?
C1 C2 1.372(7) . ?
C2 C3 1.391(7) . ?
C3 C4 1.380(6) . ?
C4 C5 1.394(6) . ?
C4 C6 1.472(6) . ?
C5 N1 1.351(6) . ?
C6 N4 1.338(6) . ?
C6 N2 1.331(6) . ?
C7 N3 1.327(6) . ?
C7 N4 1.373(6) . ?
C7 C8 1.472(6) . ?
C8 C12 1.396(6) . ?
C8 C9 1.400(6) . ?
C9 C10 1.360(7) . ?
C10 C11 1.380(7) . ?
C11 N5 1.340(6) . ?
C12 N5 1.341(6) . ?
C13 N6 1.354(6) . ?
C13 C14 1.369(7) . ?
C14 C15 1.368(7) . ?
C15 C16 1.400(7) . ?
C16 C17 1.384(7) . ?
C16 C18 1.461(6) . ?
C17 N6 1.334(6) . ?
C18 N7 1.328(6) . ?
C18 N8 1.347(6) . ?
C19 N9 1.331(6) . ?
C19 N7 1.367(6) . ?
C19 C20 1.468(6) . ?
C20 C24 1.378(7) . ?
C20 C21 1.392(7) . ?
C21 C22 1.369(7) . ?
C22 C23 1.372(7) . ?
C23 N10 1.327(6) . ?
C24 N10 1.357(6) . ?
C25 N11 1.169(6) . ?
C25 S1 1.630(5) . ?
C26 N12 1.139(6) . ?
C26 S2 1.651(5) . ?
N1 Ni1 2.170(4) . ?
N2 N3 1.355(6) . ?
N5 Ni1 2.171(4) 3_455 ?
N6 Ni1 2.167(4) . ?
N8 N9 1.366(5) . ?
N10 Ni1 2.176(4) 3_565 ?
N11 Ni1 2.030(4) . ?
N12 Ni1 2.036(4) . ?
Ni1 N5 2.171(4) 3 ?
Ni1 N10 2.176(4) 3_465 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 124.3(4) . . ?
C1 C2 C3 118.0(4) . . ?
C4 C3 C2 119.6(4) . . ?
C3 C4 C5 118.4(4) . . ?
C3 C4 C6 121.7(4) . . ?
C5 C4 C6 119.8(4) . . ?
N1 C5 C4 122.8(4) . . ?
N4 C6 N2 109.9(4) . . ?
N4 C6 C4 127.4(4) . . ?
N2 C6 C4 122.7(4) . . ?
N3 C7 N4 114.7(4) . . ?
N3 C7 C8 121.2(4) . . ?
N4 C7 C8 124.1(4) . . ?
C12 C8 C9 117.9(4) . . ?
C12 C8 C7 122.0(4) . . ?
C9 C8 C7 120.1(4) . . ?
C10 C9 C8 119.2(5) . . ?
C9 C10 C11 119.4(4) . . ?
N5 C11 C10 123.0(5) . . ?
N5 C12 C8 122.8(4) . . ?
N6 C13 C14 123.2(4) . . ?
C15 C14 C13 119.7(5) . . ?
C14 C15 C16 118.6(5) . . ?
C17 C16 C15 117.7(4) . . ?
C17 C16 C18 120.6(4) . . ?
C15 C16 C18 121.7(4) . . ?
N6 C17 C16 124.3(5) . . ?
N7 C18 N8 108.9(4) . . ?
N7 C18 C16 128.3(4) . . ?
N8 C18 C16 122.8(4) . . ?
N9 C19 N7 114.3(4) . . ?
N9 C19 C20 120.5(4) . . ?
N7 C19 C20 125.1(4) . . ?
C24 C20 C21 117.4(4) . . ?
C24 C20 C19 122.6(4) . . ?
C21 C20 C19 120.0(4) . . ?
C22 C21 C20 119.1(5) . . ?
C23 C22 C21 119.7(4) . . ?
N10 C23 C22 123.0(5) . . ?
N10 C24 C20 123.7(4) . . ?
N11 C25 S1 178.8(4) . . ?
N12 C26 S2 179.1(5) . . ?
C1 N1 C5 116.9(4) . . ?
C1 N1 Ni1 118.1(3) . . ?
C5 N1 Ni1 124.8(3) . . ?
C6 N2 N3 111.0(4) . . ?
C7 N3 N2 102.1(4) . . ?
C6 N4 C7 102.3(4) . . ?
C11 N5 C12 117.7(4) . . ?
C11 N5 Ni1 119.4(3) . 3_455 ?
C12 N5 Ni1 122.6(3) . 3_455 ?
C17 N6 C13 116.4(4) . . ?
C17 N6 Ni1 125.6(3) . . ?
C13 N6 Ni1 118.0(3) . . ?
C18 N7 C19 103.9(4) . . ?
C18 N8 N9 111.0(4) . . ?
C19 N9 N8 101.9(4) . . ?
C23 N10 C24 117.0(4) . . ?
C23 N10 Ni1 119.1(3) . 3_565 ?
C24 N10 Ni1 123.3(3) . 3_565 ?
C25 N11 Ni1 176.8(4) . . ?
C26 N12 Ni1 178.0(4) . . ?
N11 Ni1 N12 178.8(2) . . ?
N11 Ni1 N6 92.20(16) . . ?
N12 Ni1 N6 88.74(16) . . ?
N11 Ni1 N5 91.10(16) . 3 ?
N12 Ni1 N5 88.24(15) . 3 ?
N6 Ni1 N5 89.00(14) . 3 ?
N11 Ni1 N1 89.20(17) . . ?
N12 Ni1 N1 89.86(16) . . ?
N6 Ni1 N1 178.56(16) . . ?
N5 Ni1 N1 91.32(15) 3 . ?
N11 Ni1 N10 89.47(16) . 3_465 ?
N12 Ni1 N10 91.18(15) . 3_465 ?
N6 Ni1 N10 91.38(15) . 3_465 ?
N5 Ni1 N10 179.30(18) 3 3_465 ?
N1 Ni1 N10 88.29(15) . 3_465 ?

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 H1B N7 0.85 2.14 2.884(9) 145.8 .
O2 H2C S1 0.85 2.68 3.509(11) 164.3 1_655
N8 H8 S1 0.86 2.74 3.389(4) 133.3 3
C24 H24 N11 0.93 2.65 3.107(6) 110.8 3_565
C23 H23 O1 0.93 2.47 3.275(8) 145.3 3_565
C23 H23 N12 0.93 2.60 3.132(7) 116.7 3_565
C22 H22 S1 0.93 2.97 3.765(5) 144.6 1_655
C17 H17 N12 0.93 2.59 3.101(7) 115.0 .
C13 H13 N11 0.93 2.50 3.062(6) 118.8 .
C13 H13 N9 0.93 2.68 3.393(6) 134.0 3_455
C12 H12 O2 0.93 2.61 3.440(9) 148.2 1_455
C11 H11 O2 0.93 2.41 3.222(10) 145.1 3_355
C11 H11 N11 0.93 2.59 3.124(7) 117.2 3_455
C5 H5 N11 0.93 2.62 3.100(7) 112.8 .
C1 H1 N12 0.93 2.44 3.015(6) 119.9 .
C1 H1 N3 0.93 2.67 3.349(6) 130.9 3_565
O1 H1B N7 0.85 2.14 2.884(9) 145.8 .
O2 H2C S1 0.85 2.68 3.509(11) 164.3 1_655
N8 H8 S1 0.86 2.74 3.389(4) 133.3 3
C24 H24 N11 0.93 2.65 3.107(6) 110.8 3_565
C23 H23 O1 0.93 2.47 3.275(8) 145.3 3_565
C23 H23 N12 0.93 2.60 3.132(7) 116.7 3_565
C22 H22 S1 0.93 2.97 3.765(5) 144.6 1_655
C17 H17 N12 0.93 2.59 3.101(7) 115.0 .
C13 H13 N11 0.93 2.50 3.062(6) 118.8 .
C13 H13 N9 0.93 2.68 3.393(6) 134.0 3_455
C12 H12 O2 0.93 2.61 3.440(9) 148.2 1_455
C11 H11 O2 0.93 2.41 3.222(10) 145.1 3_355
C11 H11 N11 0.93 2.59 3.124(7) 117.2 3_455
C5 H5 N11 0.93 2.62 3.100(7) 112.8 .
C1 H1 N12 0.93 2.44 3.015(6) 119.9 .
C1 H1 N3 0.93 2.67 3.349(6) 130.9 3_565
O1 H1B N7 0.85 2.14 2.884(9) 145.8 .
O2 H2C S1 0.85 2.68 3.509(11) 164.3 1_655
N8 H8 S1 0.86 2.74 3.389(4) 133.3 3
C24 H24 N11 0.93 2.65 3.107(6) 110.8 3_565
C23 H23 O1 0.93 2.47 3.275(8) 145.3 3_565
C23 H23 N12 0.93 2.60 3.132(7) 116.7 3_565
C22 H22 S1 0.93 2.97 3.765(5) 144.6 1_655
C17 H17 N12 0.93 2.59 3.101(7) 115.0 .
C13 H13 N11 0.93 2.50 3.062(6) 118.8 .
C13 H13 N9 0.93 2.68 3.393(6) 134.0 3_455
C12 H12 O2 0.93 2.61 3.440(9) 148.2 1_455
C11 H11 O2 0.93 2.41 3.222(10) 145.1 3_355
C11 H11 N11 0.93 2.59 3.124(7) 117.2 3_455
C5 H5 N11 0.93 2.62 3.100(7) 112.8 .
C1 H1 N12 0.93 2.44 3.015(6) 119.9 .
C1 H1 N3 0.93 2.67 3.349(6) 130.9 3_565
C1 H1 N3 0.93 2.67 3.349(6) 130.9 3_565
C1 H1 N12 0.93 2.44 3.015(6) 119.9 .
C5 H5 N11 0.93 2.62 3.100(7) 112.8 .
C11 H11 N11 0.93 2.59 3.124(7) 117.2 3_455
C11 H11 O2 0.93 2.41 3.222(10) 145.1 3_355
C12 H12 O2 0.93 2.61 3.440(9) 148.2 1_455
C13 H13 N9 0.93 2.68 3.393(6) 134.0 3_455
C13 H13 N11 0.93 2.50 3.062(6) 118.8 .
C17 H17 N12 0.93 2.59 3.101(7) 115.0 .
C22 H22 S1 0.93 2.97 3.765(5) 144.6 1_655
C23 H23 N12 0.93 2.60 3.132(7) 116.7 3_565
C23 H23 O1 0.93 2.47 3.275(8) 145.3 3_565
C24 H24 N11 0.93 2.65 3.107(6) 110.8 3_565
N8 H8 S1 0.86 2.74 3.389(4) 133.3 3
O2 H2C S1 0.85 2.68 3.509(11) 164.3 1_655
O1 H1B N7 0.85 2.14 2.884(9) 145.8 .

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.09
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.697
_refine_diff_density_rms         0.077
####################################################################### 
# 
# 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_xb9145
_database_code_depnum_ccdc_archive 'CCDC 1458082'
_audit_update_record             
;
2016-03-06 deposited with the CCDC.
2016-07-24 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            'C26 H22 Co N12 O2 S2'
_chemical_formula_weight         657.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   17.246(7)
_cell_length_b                   9.876(4)
_cell_length_c                   16.480(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2806.9(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    553
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      16.79

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_F_000             1348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.810
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13859
_diffrn_reflns_av_unetI/netI     0.1913
_diffrn_reflns_av_R_equivalents  0.1591
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.062
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_point_group_measured_fraction_full 0.925
_reflns_number_total             4804
_reflns_number_gt                2199
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_max     0.839
_reflns_Friedel_fraction_full    0.843

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1163P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 574 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.16(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4804
_refine_ls_number_parameters     388
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1992
_refine_ls_R_factor_gt           0.0923
_refine_ls_wR_factor_ref         0.2491
_refine_ls_wR_factor_gt          0.2039
_refine_ls_goodness_of_fit_ref   0.913
_refine_ls_restrained_S_all      0.913
_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
C1 C 0.2291(10) 0.8924(17) 0.3976(13) 0.052(5) Uani 1 1 d . . . . .
H1 H 0.1758 0.9063 0.3957 0.063 Uiso 1 1 calc R U . . .
C2 C 0.2717(11) 0.9440(18) 0.3359(14) 0.061(6) Uani 1 1 d . . . . .
H2 H 0.2491 0.9948 0.2947 0.073 Uiso 1 1 calc R U . . .
C3 C 0.3510(11) 0.9176(19) 0.3370(12) 0.054(5) Uani 1 1 d . . . . .
H3 H 0.3826 0.9464 0.2947 0.065 Uiso 1 1 calc R U . . .
C4 C 0.3820(10) 0.8479(16) 0.4019(11) 0.040(5) Uani 1 1 d . . . . .
C5 C 0.3334(10) 0.8026(19) 0.4596(12) 0.041(5) Uani 1 1 d . . . . .
H5 H 0.3547 0.7528 0.5021 0.050 Uiso 1 1 calc R U . . .
C6 C 0.4641(10) 0.8194(16) 0.4064(10) 0.035(4) Uani 1 1 d . . . . .
C7 C 0.5781(10) 0.7501(18) 0.4324(12) 0.043(4) Uani 1 1 d . . . . .
C8 C 0.6429(10) 0.6648(17) 0.4588(11) 0.039(4) Uani 1 1 d . . . . .
C9 C 0.7202(10) 0.7102(19) 0.4545(13) 0.056(5) Uani 1 1 d . U . . .
H9 H 0.7314 0.7942 0.4317 0.068 Uiso 1 1 calc R U . . .
C10 C 0.7774(10) 0.6330(17) 0.4830(13) 0.051(5) Uani 1 1 d . U . . .
H10 H 0.8285 0.6624 0.4792 0.061 Uiso 1 1 calc R U . . .
C11 C 0.7610(10) 0.5093(17) 0.5182(13) 0.056(6) Uani 1 1 d . . . . .
H11 H 0.8014 0.4601 0.5412 0.068 Uiso 1 1 calc R U . . .
C12 C 0.6330(10) 0.5378(18) 0.4913(13) 0.054(5) Uani 1 1 d . . . . .
H12 H 0.5826 0.5044 0.4932 0.064 Uiso 1 1 calc R U . . .
C13 C 0.1261(10) 0.6091(16) 0.7104(12) 0.042(5) Uani 1 1 d . . . . .
H13 H 0.1794 0.5951 0.7103 0.050 Uiso 1 1 calc R U . . .
C14 C 0.0831(11) 0.5508(18) 0.7706(11) 0.047(5) Uani 1 1 d . . . . .
H14 H 0.1069 0.4972 0.8098 0.056 Uiso 1 1 calc R U . . .
C15 C 0.0027(10) 0.5726(17) 0.7726(10) 0.043(5) Uani 1 1 d . . . . .
H15 H -0.0278 0.5352 0.8134 0.051 Uiso 1 1 calc R U . . .
C16 C -0.0292(9) 0.6501(16) 0.7132(12) 0.042(4) Uani 1 1 d . . . . .
C17 C 0.0158(11) 0.7066(18) 0.6535(13) 0.050(5) Uani 1 1 d . . . . .
H17 H -0.0076 0.7598 0.6138 0.060 Uiso 1 1 calc R U . . .
C18 C -0.1154(9) 0.6732(18) 0.7082(11) 0.039(4) Uani 1 1 d . . . . .
C19 C -0.2289(10) 0.7445(17) 0.6875(10) 0.042(4) Uani 1 1 d . . . . .
C20 C -0.2929(10) 0.8314(16) 0.6574(12) 0.042(4) Uani 1 1 d . . . . .
C21 C -0.2806(10) 0.9541(17) 0.6219(10) 0.042(5) Uani 1 1 d . . . . .
H21 H -0.2303 0.9868 0.6165 0.051 Uiso 1 1 calc R U . . .
C22 C -0.4115(11) 0.975(2) 0.6020(11) 0.053(5) Uani 1 1 d . . . . .
H22 H -0.4534 1.0242 0.5823 0.063 Uiso 1 1 calc R U . . .
C23 C -0.4266(12) 0.855(2) 0.6355(15) 0.067(7) Uani 1 1 d . . . . .
H23 H -0.4775 0.8240 0.6385 0.081 Uiso 1 1 calc R U . . .
C24 C -0.3678(12) 0.776(2) 0.6655(14) 0.057(5) Uani 1 1 d . . . . .
H24 H -0.3766 0.6923 0.6896 0.068 Uiso 1 1 calc R U . . .
C25 C 0.0275(11) 0.7701(17) 0.4387(11) 0.040(5) Uani 1 1 d . . . . .
C26 C 0.3173(12) 0.742(2) 0.6823(14) 0.052(6) Uani 1 1 d . . . . .
Co1 Co 0.17439(13) 0.7568(2) 0.5567(2) 0.0421(6) Uani 1 1 d . . . . .
N1 N 0.2568(9) 0.8236(15) 0.4608(9) 0.046(4) Uani 1 1 d . . . . .
N2 N 0.5019(8) 0.7232(13) 0.4457(9) 0.043(4) Uani 1 1 d . . . . .
N3 N 0.5194(8) 0.9002(14) 0.3697(11) 0.056(4) Uani 1 1 d . . . . .
H3A H 0.5092 0.9714 0.3417 0.068 Uiso 1 1 calc R U . . .
N4 N 0.5918(8) 0.8522(15) 0.3836(11) 0.055(4) Uani 1 1 d . . . . .
N5 N 0.6892(9) 0.4574(14) 0.5206(10) 0.050(4) Uani 1 1 d . . . . .
N6 N 0.0952(8) 0.6861(15) 0.6508(10) 0.044(4) Uani 1 1 d . . . . .
N7 N -0.1659(9) 0.5905(14) 0.7426(9) 0.050(4) Uani 1 1 d . . . . .
H7 H -0.1541 0.5193 0.7700 0.060 Uiso 1 1 calc R U . . .
N8 N -0.2391(9) 0.6346(15) 0.7282(10) 0.054(4) Uani 1 1 d . . . . .
N9 N -0.1517(7) 0.7741(14) 0.6725(10) 0.043(4) Uani 1 1 d . . . . .
N10 N -0.3413(9) 1.0292(14) 0.5944(9) 0.045(4) Uani 1 1 d . . . . .
N11 N 0.0803(10) 0.7673(16) 0.4801(10) 0.054(4) Uani 1 1 d . . . . .
N12 N 0.2684(10) 0.7403(17) 0.6348(11) 0.059(5) Uani 1 1 d . . . . .
S1 S -0.0486(3) 0.7771(5) 0.3785(4) 0.0597(14) Uani 1 1 d . . . . .
S2 S 0.3886(3) 0.7350(5) 0.7464(4) 0.0702(18) Uani 1 1 d . . . . .
O2 O 0.4418(12) 0.546(2) 0.5686(15) 0.163(9) Uani 1 1 d . . . . .
H2A H 0.4377 0.4607 0.5716 0.244 Uiso 1 1 d R U . . .
H2B H 0.4655 0.5757 0.6102 0.244 Uiso 1 1 d R U . . .
O1 O 0.9110(18) 0.969(4) 0.575(4) 0.40(4) Uani 1 1 d . . . . .
H1A H 0.9198 1.0538 0.5718 0.607 Uiso 1 1 d R U . . .
H1B H 0.9317 0.9297 0.5343 0.607 Uiso 1 1 d 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
C1 N1 1.33(2) . ?
C1 C2 1.35(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.39(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.38(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.34(2) . ?
C4 C6 1.45(2) . ?
C5 N1 1.34(2) . ?
C5 H5 0.9300 . ?
C6 N2 1.32(2) . ?
C6 N3 1.38(2) . ?
C7 N4 1.31(2) . ?
C7 N2 1.36(2) . ?
C7 C8 1.47(2) . ?
C8 C12 1.37(2) . ?
C8 C9 1.41(2) . ?
C9 C10 1.33(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.38(2) . ?
C10 H10 0.9300 . ?
C11 N5 1.34(2) . ?
C11 H11 0.9300 . ?
C12 N5 1.34(2) . ?
C12 H12 0.9300 . ?
C13 N6 1.35(2) . ?
C13 C14 1.37(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.40(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.36(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.37(2) . ?
C16 C18 1.51(2) . ?
C17 N6 1.39(2) . ?
C17 H17 0.9300 . ?
C18 N9 1.31(2) . ?
C18 N7 1.32(2) . ?
C19 N8 1.29(2) . ?
C19 N9 1.39(2) . ?
C19 C20 1.48(2) . ?
C20 C21 1.36(2) . ?
C20 C24 1.41(2) . ?
C21 N10 1.36(2) . ?
C21 H21 0.9300 . ?
C22 N10 1.33(2) . ?
C22 C23 1.33(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.37(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 N11 1.14(2) . ?
C25 S1 1.647(19) . ?
C26 N12 1.15(3) . ?
C26 S2 1.62(2) . ?
Co1 N11 2.059(17) . ?
Co1 N12 2.076(18) . ?
Co1 N6 2.181(16) . ?
Co1 N5 2.212(14) 3_465 ?
Co1 N10 2.219(14) 3_575 ?
Co1 N1 2.226(15) . ?
N3 N4 1.355(18) . ?
N3 H3A 0.8600 . ?
N5 Co1 2.212(14) 3_565 ?
N7 N8 1.356(19) . ?
N7 H7 0.8600 . ?
N10 Co1 2.219(14) 3_475 ?
O2 H2A 0.8500 . ?
O2 H2B 0.8501 . ?
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
N1 C1 C2 125.8(17) . . ?
N1 C1 H1 117.1 . . ?
C2 C1 H1 117.1 . . ?
C1 C2 C3 116.9(17) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 H2 121.5 . . ?
C4 C3 C2 119.0(18) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C5 C4 C3 118.2(17) . . ?
C5 C4 C6 120.7(16) . . ?
C3 C4 C6 121.1(17) . . ?
N1 C5 C4 125.0(17) . . ?
N1 C5 H5 117.5 . . ?
C4 C5 H5 117.5 . . ?
N2 C6 N3 106.8(14) . . ?
N2 C6 C4 130.4(16) . . ?
N3 C6 C4 122.8(15) . . ?
N4 C7 N2 115.1(16) . . ?
N4 C7 C8 119.0(16) . . ?
N2 C7 C8 125.3(17) . . ?
C12 C8 C9 115.3(17) . . ?
C12 C8 C7 123.0(16) . . ?
C9 C8 C7 121.6(16) . . ?
C10 C9 C8 120.0(17) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.2(17) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
N5 C11 C10 122.6(17) . . ?
N5 C11 H11 118.7 . . ?
C10 C11 H11 118.7 . . ?
N5 C12 C8 126.2(16) . . ?
N5 C12 H12 116.9 . . ?
C8 C12 H12 116.9 . . ?
N6 C13 C14 123.4(17) . . ?
N6 C13 H13 118.3 . . ?
C14 C13 H13 118.3 . . ?
C13 C14 C15 119.3(16) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C16 C15 C14 118.0(16) . . ?
C16 C15 H15 121.0 . . ?
C14 C15 H15 121.0 . . ?
C15 C16 C17 121.2(17) . . ?
C15 C16 C18 121.6(16) . . ?
C17 C16 C18 117.2(17) . . ?
C16 C17 N6 121.5(19) . . ?
C16 C17 H17 119.3 . . ?
N6 C17 H17 119.3 . . ?
N9 C18 N7 110.3(14) . . ?
N9 C18 C16 127.5(15) . . ?
N7 C18 C16 122.2(16) . . ?
N8 C19 N9 113.7(16) . . ?
N8 C19 C20 124.1(16) . . ?
N9 C19 C20 122.2(14) . . ?
C21 C20 C24 121.9(17) . . ?
C21 C20 C19 122.9(16) . . ?
C24 C20 C19 115.2(15) . . ?
C20 C21 N10 120.6(16) . . ?
C20 C21 H21 119.7 . . ?
N10 C21 H21 119.7 . . ?
N10 C22 C23 125.2(19) . . ?
N10 C22 H22 117.4 . . ?
C23 C22 H22 117.4 . . ?
C22 C23 C24 120.6(19) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C23 C24 C20 115.1(18) . . ?
C23 C24 H24 122.4 . . ?
C20 C24 H24 122.4 . . ?
N11 C25 S1 178.9(19) . . ?
N12 C26 S2 176(2) . . ?
N11 Co1 N12 178.3(7) . . ?
N11 Co1 N6 87.7(6) . . ?
N12 Co1 N6 91.3(6) . . ?
N11 Co1 N5 88.5(6) . 3_465 ?
N12 Co1 N5 90.1(7) . 3_465 ?
N6 Co1 N5 87.5(6) . 3_465 ?
N11 Co1 N10 91.6(6) . 3_575 ?
N12 Co1 N10 89.8(6) . 3_575 ?
N6 Co1 N10 91.7(6) . 3_575 ?
N5 Co1 N10 179.2(7) 3_465 3_575 ?
N11 Co1 N1 93.0(6) . . ?
N12 Co1 N1 88.0(6) . . ?
N6 Co1 N1 178.4(6) . . ?
N5 Co1 N1 91.1(6) 3_465 . ?
N10 Co1 N1 89.7(5) 3_575 . ?
C1 N1 C5 115.0(16) . . ?
C1 N1 Co1 118.5(12) . . ?
C5 N1 Co1 126.5(12) . . ?
C6 N2 C7 104.9(15) . . ?
N4 N3 C6 111.1(14) . . ?
N4 N3 H3A 124.5 . . ?
C6 N3 H3A 124.5 . . ?
C7 N4 N3 101.9(15) . . ?
C12 N5 C11 115.4(14) . . ?
C12 N5 Co1 125.4(12) . 3_565 ?
C11 N5 Co1 118.7(12) . 3_565 ?
C13 N6 C17 116.7(16) . . ?
C13 N6 Co1 116.7(11) . . ?
C17 N6 Co1 126.5(13) . . ?
C18 N7 N8 109.8(14) . . ?
C18 N7 H7 125.1 . . ?
N8 N7 H7 125.1 . . ?
C19 N8 N7 103.6(14) . . ?
C18 N9 C19 102.5(14) . . ?
C22 N10 C21 116.6(16) . . ?
C22 N10 Co1 121.5(13) . 3_475 ?
C21 N10 Co1 121.2(12) . 3_475 ?
C25 N11 Co1 178.1(17) . . ?
C26 N12 Co1 173.2(18) . . ?
H2A O2 H2B 109.5 . . ?
H1A O1 H1B 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
N1 C1 C2 C3 3(3) . . . . ?
C1 C2 C3 C4 -3(3) . . . . ?
C2 C3 C4 C5 3(3) . . . . ?
C2 C3 C4 C6 -179.2(17) . . . . ?
C3 C4 C5 N1 -2(3) . . . . ?
C6 C4 C5 N1 -179.9(16) . . . . ?
C5 C4 C6 N2 22(3) . . . . ?
C3 C4 C6 N2 -155.8(17) . . . . ?
C5 C4 C6 N3 -155.0(17) . . . . ?
C3 C4 C6 N3 27(2) . . . . ?
N4 C7 C8 C12 -162.4(19) . . . . ?
N2 C7 C8 C12 9(3) . . . . ?
N4 C7 C8 C9 20(3) . . . . ?
N2 C7 C8 C9 -169.4(17) . . . . ?
C12 C8 C9 C10 -2(3) . . . . ?
C7 C8 C9 C10 176.4(19) . . . . ?
C8 C9 C10 C11 -1(3) . . . . ?
C9 C10 C11 N5 5(3) . . . . ?
C9 C8 C12 N5 2(3) . . . . ?
C7 C8 C12 N5 -176.2(18) . . . . ?
N6 C13 C14 C15 -1(3) . . . . ?
C13 C14 C15 C16 1(2) . . . . ?
C14 C15 C16 C17 -1(3) . . . . ?
C14 C15 C16 C18 176.9(15) . . . . ?
C15 C16 C17 N6 1(3) . . . . ?
C18 C16 C17 N6 -177.2(16) . . . . ?
C15 C16 C18 N9 157.0(18) . . . . ?
C17 C16 C18 N9 -25(3) . . . . ?
C15 C16 C18 N7 -22(3) . . . . ?
C17 C16 C18 N7 156.1(17) . . . . ?
N8 C19 C20 C21 173.0(18) . . . . ?
N9 C19 C20 C21 -8(3) . . . . ?
N8 C19 C20 C24 -9(3) . . . . ?
N9 C19 C20 C24 169.6(16) . . . . ?
C24 C20 C21 N10 1(3) . . . . ?
C19 C20 C21 N10 179.2(15) . . . . ?
N10 C22 C23 C24 0(3) . . . . ?
C22 C23 C24 C20 0(3) . . . . ?
C21 C20 C24 C23 0(3) . . . . ?
C19 C20 C24 C23 -178.1(19) . . . . ?
C2 C1 N1 C5 -2(3) . . . . ?
C2 C1 N1 Co1 177.5(16) . . . . ?
C4 C5 N1 C1 2(3) . . . . ?
C4 C5 N1 Co1 -177.8(14) . . . . ?
N3 C6 N2 C7 0.8(18) . . . . ?
C4 C6 N2 C7 -176.3(17) . . . . ?
N4 C7 N2 C6 -4(2) . . . . ?
C8 C7 N2 C6 -175.0(16) . . . . ?
N2 C6 N3 N4 2.0(19) . . . . ?
C4 C6 N3 N4 179.5(15) . . . . ?
N2 C7 N4 N3 5(2) . . . . ?
C8 C7 N4 N3 176.7(16) . . . . ?
C6 N3 N4 C7 -4(2) . . . . ?
C8 C12 N5 C11 1(3) . . . . ?
C8 C12 N5 Co1 -170.9(15) . . . 3_565 ?
C10 C11 N5 C12 -4(3) . . . . ?
C10 C11 N5 Co1 168.2(16) . . . 3_565 ?
C14 C13 N6 C17 1(3) . . . . ?
C14 C13 N6 Co1 -175.9(13) . . . . ?
C16 C17 N6 C13 -1(3) . . . . ?
C16 C17 N6 Co1 175.8(13) . . . . ?
N9 C18 N7 N8 2(2) . . . . ?
C16 C18 N7 N8 -179.6(16) . . . . ?
N9 C19 N8 N7 1.5(19) . . . . ?
C20 C19 N8 N7 -179.9(16) . . . . ?
C18 N7 N8 C19 -1.8(18) . . . . ?
N7 C18 N9 C19 -0.6(19) . . . . ?
C16 C18 N9 C19 -179.4(16) . . . . ?
N8 C19 N9 C18 -1(2) . . . . ?
C20 C19 N9 C18 -179.3(16) . . . . ?
C23 C22 N10 C21 1(3) . . . . ?
C23 C22 N10 Co1 -169.5(16) . . . 3_475 ?
C20 C21 N10 C22 -2(2) . . . . ?
C20 C21 N10 Co1 169.0(13) . . . 3_475 ?

_refine_diff_density_max         0.938
_refine_diff_density_min         -0.728
_refine_diff_density_rms         0.105

_shelxl_version_number           2014/6



