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

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

data_b614
_database_code_depnum_ccdc_archive 'CCDC 1550647'
_audit_update_record             
;
2017-05-17 deposited with the CCDC.
2017-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C19H20N10Ni
_chemical_formula_sum            'C19.50 H21 Cl N10 Ni'
_chemical_formula_weight         489.62

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.1139(9)
_cell_length_b                   11.2775(13)
_cell_length_c                   12.7151(14)
_cell_angle_alpha                93.185(3)
_cell_angle_beta                 104.866(3)
_cell_angle_gamma                107.323(2)
_cell_volume                     1062.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    636
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      22.63

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_F_000             506
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    1.069
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.4795
_exptl_absorpt_correction_T_max  0.5629
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8800
_diffrn_reflns_av_unetI/netI     0.0828
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.674
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4864
_reflns_number_gt                3464
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'APEX3 v2016.1-0 (Bruker AXS)'
_computing_data_collection       'APEX3 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL--2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXT--(Sheldrick 2015)'
_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)+(0.0912P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4864
_refine_ls_number_parameters     300
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0617
_refine_ls_wR_factor_ref         0.1715
_refine_ls_wR_factor_gt          0.1434
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.74107(7) 0.63733(4) 0.66486(4) 0.02057(18) Uani 1 1 d . . . . .
N1 N 0.7829(4) 0.9025(3) 0.6764(3) 0.0214(7) Uani 1 1 d . . . . .
N2 N 0.5030(4) 0.7845(3) 0.6153(3) 0.0199(7) Uani 1 1 d . . . . .
N3 N 0.5170(4) 0.6074(3) 0.8117(3) 0.0219(7) Uani 1 1 d . . . . .
N4 N 0.7998(4) 0.6943(3) 0.8982(3) 0.0218(7) Uani 1 1 d . . . . .
N5 N 0.7967(6) 0.6319(3) 0.5281(3) 0.0345(9) Uani 1 1 d . . . . .
N6 N 0.8643(4) 0.7113(3) 0.4827(3) 0.0225(7) Uani 1 1 d . . . . .
N7 N 0.9305(5) 0.7853(4) 0.4314(3) 0.0359(9) Uani 1 1 d . . . . .
N8 N 0.8108(6) 0.4900(3) 0.6897(3) 0.0328(9) Uani 1 1 d . . . . .
N9 N 0.8818(4) 0.4627(3) 0.7719(3) 0.0248(8) Uani 1 1 d . . . . .
N10 N 0.9544(5) 0.4294(4) 0.8496(4) 0.0412(10) Uani 1 1 d . . . . .
C1 C 0.6741(5) 0.7812(3) 0.6476(3) 0.0207(8) Uani 1 1 d . . . . .
C2 C 0.6812(5) 0.9837(4) 0.6638(3) 0.0221(8) Uani 1 1 d . . . . .
C3 C 0.7304(6) 1.1145(3) 0.6818(3) 0.0253(9) Uani 1 1 d . . . . .
H3 H 0.8503 1.1652 0.7070 0.030 Uiso 1 1 calc R U . . .
C4 C 0.5901(6) 1.1646(4) 0.6597(3) 0.0265(9) Uani 1 1 d . . . . .
H4 H 0.6169 1.2512 0.6722 0.032 Uiso 1 1 calc R U . . .
C5 C 0.4102(6) 1.0891(4) 0.6193(3) 0.0267(9) Uani 1 1 d . . . . .
H5 H 0.3206 1.1266 0.6047 0.032 Uiso 1 1 calc R U . . .
C6 C 0.3616(6) 0.9585(4) 0.6002(4) 0.0258(9) Uani 1 1 d . . . . .
H6 H 0.2420 0.9077 0.5726 0.031 Uiso 1 1 calc R U . . .
C7 C 0.5024(5) 0.9086(3) 0.6249(3) 0.0214(8) Uani 1 1 d . . . . .
C8 C 0.9789(5) 0.9435(4) 0.7119(4) 0.0280(9) Uani 1 1 d . . . . .
H8A H 1.0216 0.9779 0.7884 0.042 Uiso 1 1 calc R U . . .
H8B H 1.0251 1.0065 0.6696 0.042 Uiso 1 1 calc R U . . .
H8C H 1.0195 0.8732 0.7012 0.042 Uiso 1 1 calc R U . . .
C9 C 0.3397(5) 0.6747(3) 0.5719(3) 0.0223(8) Uani 1 1 d . . . . .
H9A H 0.3698 0.6103 0.5343 0.027 Uiso 1 1 calc R U . . .
H9B H 0.2515 0.6988 0.5180 0.027 Uiso 1 1 calc R U . . .
C10 C 0.2556(5) 0.6198(4) 0.6586(3) 0.0251(9) Uani 1 1 d . . . . .
H10A H 0.1310 0.5698 0.6231 0.030 Uiso 1 1 calc R U . . .
H10B H 0.2555 0.6880 0.7084 0.030 Uiso 1 1 calc R U . . .
C11 C 0.3491(5) 0.5379(4) 0.7258(3) 0.0243(9) Uani 1 1 d . . . . .
H11A H 0.2659 0.4854 0.7603 0.029 Uiso 1 1 calc R U . . .
H11B H 0.3760 0.4829 0.6761 0.029 Uiso 1 1 calc R U . . .
C12 C 0.6838(5) 0.6428(3) 0.7975(3) 0.0223(8) Uani 1 1 d . . . . .
C13 C 0.5251(6) 0.6381(4) 0.9207(3) 0.0243(9) Uani 1 1 d . . . . .
C14 C 0.3934(6) 0.6222(4) 0.9740(4) 0.0307(10) Uani 1 1 d . . . . .
H14 H 0.2720 0.5835 0.9373 0.037 Uiso 1 1 calc R U . . .
C15 C 0.4534(7) 0.6680(5) 1.0867(4) 0.0373(11) Uani 1 1 d . . . . .
H15 H 0.3693 0.6612 1.1257 0.045 Uiso 1 1 calc R U . . .
C16 C 0.6372(7) 0.7236(5) 1.1419(4) 0.0372(11) Uani 1 1 d . . . . .
H16 H 0.6724 0.7519 1.2169 0.045 Uiso 1 1 calc R U . . .
C17 C 0.7671(6) 0.7373(4) 1.0874(4) 0.0318(10) Uani 1 1 d . . . . .
H17 H 0.8891 0.7742 1.1237 0.038 Uiso 1 1 calc R U . . .
C18 C 0.7066(5) 0.6934(4) 0.9760(3) 0.0232(9) Uani 1 1 d . . . . .
C19 C 0.9956(5) 0.7414(4) 0.9250(4) 0.0291(10) Uani 1 1 d . . . . .
H19A H 1.0318 0.7259 0.8608 0.044 Uiso 1 1 calc R U . . .
H19B H 1.0465 0.6994 0.9820 0.044 Uiso 1 1 calc R U . . .
H19C H 1.0376 0.8300 0.9499 0.044 Uiso 1 1 calc R U . . .
Cl1B Cl 0.4491(9) 0.9533(4) -0.1175(4) 0.1072(18) Uani 0.5 1 d D . P A -1
Cl1A Cl 0.3819(6) 1.0242(4) 0.0811(3) 0.0911(14) Uani 0.5 1 d D . P A -1
C1S C 0.523(3) 0.986(3) 0.0187(13) 0.117(7) Uani 0.5 1 d D U P A -1
H1SA H 0.6355 1.0556 0.0384 0.141 Uiso 0.5 1 calc R U P A -1
H1SB H 0.5497 0.9142 0.0478 0.141 Uiso 0.5 1 calc R U P A -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 C12 1.864(4) . ?
Ni1 C1 1.866(4) . ?
Ni1 N5 1.908(4) . ?
Ni1 N8 1.925(4) . ?
N1 C1 1.358(5) . ?
N1 C2 1.394(5) . ?
N1 C8 1.455(5) . ?
N2 C1 1.355(5) . ?
N2 C7 1.400(5) . ?
N2 C9 1.472(5) . ?
N3 C12 1.354(5) . ?
N3 C13 1.390(5) . ?
N3 C11 1.473(5) . ?
N4 C12 1.355(5) . ?
N4 C18 1.390(5) . ?
N4 C19 1.457(5) . ?
N5 N6 1.167(5) . ?
N6 N7 1.176(5) . ?
N8 N9 1.162(5) . ?
N9 N10 1.157(5) . ?
C2 C7 1.386(5) . ?
C2 C3 1.398(5) . ?
C3 C4 1.389(6) . ?
C4 C5 1.395(6) . ?
C5 C6 1.396(5) . ?
C6 C7 1.392(6) . ?
C9 C10 1.508(5) . ?
C10 C11 1.526(6) . ?
C13 C14 1.379(6) . ?
C13 C18 1.387(6) . ?
C14 C15 1.403(6) . ?
C15 C16 1.403(7) . ?
C16 C17 1.380(7) . ?
C17 C18 1.382(6) . ?
Cl1B C1S 1.662(15) . ?
Cl1A C1S 1.687(17) . ?

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
C12 Ni1 C1 85.46(17) . . ?
C12 Ni1 N5 179.23(18) . . ?
C1 Ni1 N5 94.05(16) . . ?
C12 Ni1 N8 92.00(16) . . ?
C1 Ni1 N8 177.37(17) . . ?
N5 Ni1 N8 88.50(16) . . ?
C1 N1 C2 110.7(3) . . ?
C1 N1 C8 125.1(3) . . ?
C2 N1 C8 124.2(3) . . ?
C1 N2 C7 110.4(3) . . ?
C1 N2 C9 125.6(3) . . ?
C7 N2 C9 124.0(3) . . ?
C12 N3 C13 111.0(3) . . ?
C12 N3 C11 125.2(3) . . ?
C13 N3 C11 123.7(3) . . ?
C12 N4 C18 110.5(3) . . ?
C12 N4 C19 126.1(4) . . ?
C18 N4 C19 123.3(3) . . ?
N6 N5 Ni1 131.7(3) . . ?
N5 N6 N7 175.6(4) . . ?
N9 N8 Ni1 129.0(3) . . ?
N10 N9 N8 175.4(4) . . ?
N2 C1 N1 106.3(3) . . ?
N2 C1 Ni1 125.9(3) . . ?
N1 C1 Ni1 127.4(3) . . ?
C7 C2 N1 106.3(3) . . ?
C7 C2 C3 121.7(4) . . ?
N1 C2 C3 132.0(4) . . ?
C4 C3 C2 116.2(4) . . ?
C3 C4 C5 122.1(4) . . ?
C4 C5 C6 121.5(4) . . ?
C7 C6 C5 116.2(4) . . ?
C2 C7 C6 122.2(4) . . ?
C2 C7 N2 106.3(3) . . ?
C6 C7 N2 131.4(4) . . ?
N2 C9 C10 114.0(3) . . ?
C9 C10 C11 114.9(3) . . ?
N3 C11 C10 115.0(3) . . ?
N3 C12 N4 106.0(3) . . ?
N3 C12 Ni1 127.1(3) . . ?
N4 C12 Ni1 126.6(3) . . ?
C14 C13 C18 121.9(4) . . ?
C14 C13 N3 132.2(4) . . ?
C18 C13 N3 105.8(3) . . ?
C13 C14 C15 116.1(4) . . ?
C14 C15 C16 121.6(4) . . ?
C17 C16 C15 121.4(4) . . ?
C16 C17 C18 116.6(4) . . ?
C17 C18 C13 122.4(4) . . ?
C17 C18 N4 131.0(4) . . ?
C13 C18 N4 106.6(3) . . ?
Cl1B C1S Cl1A 115.9(10) . . ?

_refine_diff_density_max         0.941
_refine_diff_density_min         -0.922
_refine_diff_density_rms         0.154


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethan/hexane'
####################################################################### 
# 
# 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_B635
_database_code_depnum_ccdc_archive 'CCDC 1550648'
_audit_update_record             
;
2017-05-17 deposited with the CCDC.
2017-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C19H20I2N4Ni
_chemical_formula_sum            'C23 H25 Cl I2 N4 Ni'
_chemical_formula_weight         705.43

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.6988(13)
_cell_length_b                   12.4353(19)
_cell_length_c                   13.505(2)
_cell_angle_alpha                105.180(2)
_cell_angle_beta                 102.756(2)
_cell_angle_gamma                108.548(2)
_cell_volume                     1260.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3061
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      22.91

_exptl_crystal_description       Plate
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.858
_exptl_crystal_F_000             684
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    3.342
_shelx_estimated_absorpt_T_min   0.379
_shelx_estimated_absorpt_T_max   0.825
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5524
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(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            16785
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.851
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5816
_reflns_number_gt                4274
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'APEX3 v2016.1-0 (Bruker AXS)'
_computing_data_collection       'APEX3 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL--2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXT--(Sheldrick 2015)'
_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)+(0.0722P)²+2.9995P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5816
_refine_ls_number_parameters     280
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0589
_refine_ls_wR_factor_ref         0.1537
_refine_ls_wR_factor_gt          0.1415
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni -0.05340(12) 0.42127(8) 0.18779(7) 0.0338(2) Uani 1 1 d . . . . .
I1 I -0.32248(6) 0.40990(5) 0.05777(4) 0.04504(16) Uani 1 1 d . . . . .
I2 I 0.02979(8) 0.63340(5) 0.31816(4) 0.04872(18) Uani 1 1 d . . . . .
N1 N -0.0659(7) 0.2263(5) 0.0108(4) 0.0337(12) Uani 1 1 d . . . . .
N2 N -0.2025(7) 0.1609(5) 0.1133(5) 0.0365(13) Uani 1 1 d . . . . .
N3 N 0.1222(7) 0.3489(5) 0.3449(4) 0.0341(12) Uani 1 1 d . . . . .
N4 N 0.2969(8) 0.4397(5) 0.2733(4) 0.0347(12) Uani 1 1 d . . . . .
C1 C -0.1095(9) 0.2626(6) 0.0995(5) 0.0367(15) Uani 1 1 d . . . . .
C2 C -0.1362(9) 0.0997(6) -0.0353(6) 0.0365(15) Uani 1 1 d . . . . .
C3 C -0.1270(10) 0.0221(7) -0.1255(6) 0.0443(17) Uani 1 1 d . . . . .
H3 H -0.0645 0.0514 -0.1691 0.053 Uiso 1 1 calc R U . . .
C4 C -0.2142(10) -0.1013(7) -0.1491(7) 0.054(2) Uani 1 1 d . . . . .
H4 H -0.2131 -0.1580 -0.2114 0.065 Uiso 1 1 calc R U . . .
C5 C -0.3027(10) -0.1440(7) -0.0842(7) 0.0463(18) Uani 1 1 d . . . . .
H5 H -0.3603 -0.2291 -0.1029 0.056 Uiso 1 1 calc R U . . .
C6 C -0.3091(10) -0.0657(7) 0.0069(7) 0.0459(18) Uani 1 1 d . . . . .
H6 H -0.3689 -0.0951 0.0516 0.055 Uiso 1 1 calc R U . . .
C7 C -0.2251(8) 0.0573(7) 0.0303(6) 0.0358(15) Uani 1 1 d . . . . .
C8 C 0.0305(10) 0.3056(7) -0.0349(6) 0.0409(16) Uani 1 1 d . . . . .
H8A H 0.0536 0.3900 0.0061 0.061 Uiso 1 1 calc R U . . .
H8B H -0.0361 0.2838 -0.1111 0.061 Uiso 1 1 calc R U . . .
H8C H 0.1396 0.2968 -0.0306 0.061 Uiso 1 1 calc R U . . .
C9 C -0.2794(10) 0.1605(7) 0.1995(6) 0.0418(17) Uani 1 1 d . . . . .
H9A H -0.3794 0.0821 0.1749 0.050 Uiso 1 1 calc R U . . .
H9B H -0.3231 0.2257 0.2101 0.050 Uiso 1 1 calc R U . . .
C10 C -0.1586(10) 0.1788(7) 0.3091(6) 0.0455(18) Uani 1 1 d . . . . .
H10A H -0.2295 0.1501 0.3525 0.055 Uiso 1 1 calc R U . . .
H10B H -0.0950 0.1261 0.2957 0.055 Uiso 1 1 calc R U . . .
C11 C -0.0288(10) 0.3071(7) 0.3770(6) 0.0427(17) Uani 1 1 d . . . . .
H11A H -0.0875 0.3631 0.3742 0.051 Uiso 1 1 calc R U . . .
H11B H 0.0100 0.3128 0.4535 0.051 Uiso 1 1 calc R U . . .
C12 C 0.1326(9) 0.4083(6) 0.2745(5) 0.0344(15) Uani 1 1 d . . . . .
C13 C 0.3896(9) 0.4013(6) 0.3446(5) 0.0318(14) Uani 1 1 d . . . . .
C14 C 0.5597(10) 0.4130(7) 0.3701(5) 0.0392(16) Uani 1 1 d . . . . .
H14 H 0.6369 0.4536 0.3389 0.047 Uiso 1 1 calc R U . . .
C15 C 0.6082(10) 0.3606(7) 0.4447(6) 0.0438(17) Uani 1 1 d . . . . .
H15 H 0.7236 0.3677 0.4670 0.053 Uiso 1 1 calc R U . . .
C16 C 0.4940(10) 0.2991(7) 0.4871(6) 0.0414(17) Uani 1 1 d . . . . .
H16 H 0.5326 0.2627 0.5356 0.050 Uiso 1 1 calc R U . . .
C17 C 0.3264(10) 0.2882(7) 0.4620(5) 0.0402(16) Uani 1 1 d . . . . .
H17 H 0.2488 0.2467 0.4924 0.048 Uiso 1 1 calc R U . . .
C18 C 0.2778(9) 0.3426(6) 0.3885(5) 0.0321(14) Uani 1 1 d . . . . .
C19 C 0.3724(10) 0.5155(7) 0.2153(6) 0.0447(18) Uani 1 1 d . . . . .
H19A H 0.2858 0.5385 0.1769 0.067 Uiso 1 1 calc R U . . .
H19B H 0.4112 0.4697 0.1627 0.067 Uiso 1 1 calc R U . . .
H19C H 0.4705 0.5889 0.2676 0.067 Uiso 1 1 calc R U . . .
C1X C 0.472(2) 0.8404(16) 0.2416(14) 0.055(4) Uani 0.5 1 d D . P A -1
H1X1 H 0.3846 0.7635 0.2370 0.083 Uiso 0.5 1 calc R U P A -1
H1X2 H 0.4439 0.8451 0.1681 0.083 Uiso 0.5 1 calc R U P A -1
Cl1A Cl 0.6617(13) 0.8314(8) 0.2719(9) 0.140(3) Uani 0.5 1 d D . P A -1
Cl2A Cl 0.4472(13) 0.9583(9) 0.3274(12) 0.184(5) Uani 0.5 1 d D . P A -1
C1S C 0.601(2) 0.900(2) 0.3294(18) 0.147(6) Uani 0.5 1 d DG U P B -2
C2S C 0.692(3) 0.9782(19) 0.4364(18) 0.147(6) Uani 0.5 1 d DG U P B -2
H2S H 0.6387 1.0190 0.4777 0.177 Uiso 0.5 1 calc R U P B -2
C3S C 0.862(3) 0.997(2) 0.4830(16) 0.147(6) Uani 0.5 1 d G U P B -2
H3S H 0.9250 1.0504 0.5561 0.177 Uiso 0.5 1 calc R U P B -2
C4S C 0.941(2) 0.937(2) 0.423(2) 0.147(6) Uani 0.5 1 d G U P B -2
H4S H 1.0569 0.9498 0.4544 0.177 Uiso 0.5 1 calc R U P B -2
C5S C 0.849(3) 0.859(2) 0.316(2) 0.147(6) Uani 0.5 1 d G U P B -2
H5S H 0.9025 0.8179 0.2743 0.177 Uiso 0.5 1 calc R U P B -2
C6S C 0.679(3) 0.840(2) 0.2690(17) 0.147(6) Uani 0.5 1 d DG U P B -2
H6S H 0.6162 0.7865 0.1959 0.177 Uiso 0.5 1 calc R U P B -2
C7S C 0.423(3) 0.887(3) 0.269(3) 0.147(6) Uani 0.5 1 d D U P B -2
H7S1 H 0.4126 0.9648 0.2947 0.221 Uiso 0.5 1 calc R U P B -2
H7S2 H 0.3360 0.8248 0.2822 0.221 Uiso 0.5 1 calc R U P B -2
H7S3 H 0.4053 0.8627 0.1908 0.221 Uiso 0.5 1 calc R U P B -2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 C12 1.856(7) . ?
Ni1 C1 1.858(7) . ?
Ni1 I2 2.5244(11) . ?
Ni1 I1 2.5350(10) . ?
N1 C1 1.345(9) . ?
N1 C2 1.396(9) . ?
N1 C8 1.441(8) . ?
N2 C1 1.352(9) . ?
N2 C7 1.392(9) . ?
N2 C9 1.467(9) . ?
N3 C12 1.350(8) . ?
N3 C18 1.387(9) . ?
N3 C11 1.455(9) . ?
N4 C12 1.361(9) . ?
N4 C13 1.396(8) . ?
N4 C19 1.467(9) . ?
C2 C3 1.377(10) . ?
C2 C7 1.396(10) . ?
C3 C4 1.388(11) . ?
C4 C5 1.387(12) . ?
C5 C6 1.379(11) . ?
C6 C7 1.381(10) . ?
C9 C10 1.527(10) . ?
C10 C11 1.514(11) . ?
C13 C18 1.364(10) . ?
C13 C14 1.393(10) . ?
C14 C15 1.397(10) . ?
C15 C16 1.377(11) . ?
C16 C17 1.375(10) . ?
C17 C18 1.404(9) . ?
C1X Cl1A 1.660(15) . ?
C1X Cl2A 1.719(19) . ?
C1S C2S 1.3900 . ?
C1S C6S 1.3900 . ?
C1S C7S 1.516(2) . ?
C2S C3S 1.3900 . ?
C3S C4S 1.3900 . ?
C4S C5S 1.3900 . ?
C5S C6S 1.3900 . ?

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
C12 Ni1 C1 86.2(3) . . ?
C12 Ni1 I2 90.8(2) . . ?
C1 Ni1 I2 176.3(2) . . ?
C12 Ni1 I1 172.7(2) . . ?
C1 Ni1 I1 86.8(2) . . ?
I2 Ni1 I1 96.22(3) . . ?
C1 N1 C2 110.3(6) . . ?
C1 N1 C8 125.5(6) . . ?
C2 N1 C8 124.1(6) . . ?
C1 N2 C7 110.8(6) . . ?
C1 N2 C9 124.2(6) . . ?
C7 N2 C9 124.8(6) . . ?
C12 N3 C18 111.0(6) . . ?
C12 N3 C11 123.7(6) . . ?
C18 N3 C11 125.1(6) . . ?
C12 N4 C13 110.5(6) . . ?
C12 N4 C19 124.9(6) . . ?
C13 N4 C19 124.2(6) . . ?
N1 C1 N2 106.8(6) . . ?
N1 C1 Ni1 127.2(5) . . ?
N2 C1 Ni1 126.0(5) . . ?
C3 C2 N1 131.4(7) . . ?
C3 C2 C7 122.2(7) . . ?
N1 C2 C7 106.5(6) . . ?
C2 C3 C4 116.3(7) . . ?
C5 C4 C3 121.8(7) . . ?
C6 C5 C4 121.5(7) . . ?
C5 C6 C7 117.2(7) . . ?
C6 C7 N2 133.4(7) . . ?
C6 C7 C2 121.0(7) . . ?
N2 C7 C2 105.5(6) . . ?
N2 C9 C10 115.1(6) . . ?
C11 C10 C9 116.6(6) . . ?
N3 C11 C10 115.8(6) . . ?
N3 C12 N4 105.4(6) . . ?
N3 C12 Ni1 124.3(5) . . ?
N4 C12 Ni1 129.9(5) . . ?
C18 C13 C14 122.8(6) . . ?
C18 C13 N4 106.3(6) . . ?
C14 C13 N4 130.9(6) . . ?
C13 C14 C15 115.0(7) . . ?
C16 C15 C14 122.0(7) . . ?
C17 C16 C15 122.7(7) . . ?
C16 C17 C18 115.4(7) . . ?
C13 C18 N3 106.8(6) . . ?
C13 C18 C17 122.0(7) . . ?
N3 C18 C17 131.2(7) . . ?
Cl1A C1X Cl2A 118.1(11) . . ?
C2S C1S C6S 120.0 . . ?
C2S C1S C7S 122.9(11) . . ?
C6S C1S C7S 116.7(11) . . ?
C1S C2S C3S 120.0 . . ?
C4S C3S C2S 120.0 . . ?
C5S C4S C3S 120.0 . . ?
C4S C5S C6S 120.0 . . ?
C5S C6S C1S 120.0 . . ?

_refine_diff_density_max         2.784
_refine_diff_density_min         -1.579
_refine_diff_density_rms         0.165


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/toluene'
####################################################################### 
# 
# 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_C179
_database_code_depnum_ccdc_archive 'CCDC 1550650'
_audit_update_record             
;
2017-05-17 deposited with the CCDC.
2017-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H26 Ag2 N4 O4'
_chemical_formula_weight         638.22

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'
Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

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

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

_cell_length_a                   16.9338(16)
_cell_length_b                   8.5206(8)
_cell_length_c                   16.0788(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2319.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4089
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      27.83

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.827
_exptl_crystal_F_000             1272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.726
_shelx_estimated_absorpt_T_min   0.626
_shelx_estimated_absorpt_T_max   0.934
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6407
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(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            15192
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.405
_diffrn_reflns_theta_max         27.496
_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 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2669
_reflns_number_gt                2227
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'APEX3 v2016.1-0 (Bruker AXS)'
_computing_data_collection       'APEX3 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL--2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXT--(Sheldrick 2015)'
_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)+(0.0285P)²+2.2976P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2669
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0272
_refine_ls_wR_factor_ref         0.0658
_refine_ls_wR_factor_gt          0.0625
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ag1 Ag 0.43999(2) 0.29719(2) 0.31416(2) 0.01940(8) Uani 1 1 d . . . . .
O1 O 0.36499(12) 0.4380(2) 0.24125(12) 0.0249(4) Uani 1 1 d . . . . .
O2 O 0.34605(12) 0.5778(2) 0.35581(13) 0.0285(5) Uani 1 1 d . . . . .
N1 N 0.57315(14) 0.1732(3) 0.42715(14) 0.0187(5) Uani 1 1 d . . . . .
N2 N 0.51168(12) -0.0190(3) 0.36820(13) 0.0149(4) Uani 1 1 d . . . . .
C1 C 0.51458(16) 0.1399(3) 0.37293(16) 0.0173(5) Uani 1 1 d . . . . .
C2 C 0.60692(15) 0.0370(3) 0.45849(15) 0.0167(5) Uani 1 1 d . . . . .
C3 C 0.66713(15) 0.0124(3) 0.51589(17) 0.0205(6) Uani 1 1 d . . . . .
H3 H 0.6946 0.0974 0.5409 0.025 Uiso 1 1 calc R U . . .
C4 C 0.68481(16) -0.1412(3) 0.53467(16) 0.0209(6) Uani 1 1 d . . . . .
H4 H 0.7257 -0.1628 0.5735 0.025 Uiso 1 1 calc R U . . .
C5 C 0.64407(17) -0.2667(3) 0.49797(17) 0.0219(6) Uani 1 1 d . . . . .
H5 H 0.6574 -0.3712 0.5132 0.026 Uiso 1 1 calc R U . . .
C6 C 0.58484(17) -0.2416(3) 0.43998(17) 0.0199(6) Uani 1 1 d . . . . .
H6 H 0.5575 -0.3262 0.4145 0.024 Uiso 1 1 calc R U . . .
C7 C 0.56748(15) -0.0861(3) 0.42092(16) 0.0159(5) Uani 1 1 d . . . . .
C8 C 0.5979(2) 0.3318(3) 0.44954(19) 0.0260(6) Uani 1 1 d . . . . .
H8A H 0.6471 0.3575 0.4205 0.039 Uiso 1 1 calc R U . . .
H8B H 0.6064 0.3377 0.5097 0.039 Uiso 1 1 calc R U . . .
H8C H 0.5567 0.4066 0.4334 0.039 Uiso 1 1 calc R U . . .
C9 C 0.45761(15) -0.1087(3) 0.31605(16) 0.0175(5) Uani 1 1 d . . . . .
H9A H 0.4205 -0.0355 0.2885 0.021 Uiso 1 1 calc R U . . .
H9B H 0.4263 -0.1801 0.3517 0.021 Uiso 1 1 calc R U . . .
C10 C 0.5000 -0.2047(4) 0.2500 0.0171(7) Uani 1 2 d S T P . .
H10A H 0.5391 -0.2733 0.2778 0.021 Uiso 0.5 1 calc R U P . .
H10B H 0.4609 -0.2733 0.2222 0.021 Uiso 0.5 1 calc R U P . .
C11 C 0.33149(15) 0.5462(3) 0.28280(18) 0.0200(6) Uani 1 1 d . . . . .
C12 C 0.26981(19) 0.6393(4) 0.2351(2) 0.0381(8) Uani 1 1 d . . . . .
H12A H 0.2659 0.5986 0.1783 0.057 Uiso 1 1 calc R U . . .
H12B H 0.2185 0.6292 0.2629 0.057 Uiso 1 1 calc R U . . .
H12C H 0.2852 0.7501 0.2334 0.057 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ag1 C1 2.070(3) . ?
Ag1 O1 2.1041(19) . ?
Ag1 Ag1 2.8961(4) 3_655 ?
O1 C11 1.272(3) . ?
O2 C11 1.229(4) . ?
N1 C1 1.351(3) . ?
N1 C2 1.389(3) . ?
N1 C8 1.460(3) . ?
N2 C1 1.357(3) . ?
N2 C7 1.392(3) . ?
N2 C9 1.458(3) . ?
C2 C7 1.382(4) . ?
C2 C3 1.391(4) . ?
C3 C4 1.377(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.403(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.391(4) . ?
C6 H6 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.521(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C9 1.521(3) 3_655 ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.519(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Ag1 O1 172.72(9) . . ?
C1 Ag1 Ag1 84.09(7) . 3_655 ?
O1 Ag1 Ag1 91.53(6) . 3_655 ?
C11 O1 Ag1 112.95(17) . . ?
C1 N1 C2 111.2(2) . . ?
C1 N1 C8 124.3(2) . . ?
C2 N1 C8 124.5(2) . . ?
C1 N2 C7 110.6(2) . . ?
C1 N2 C9 125.3(2) . . ?
C7 N2 C9 124.1(2) . . ?
N1 C1 N2 105.8(2) . . ?
N1 C1 Ag1 127.37(19) . . ?
N2 C1 Ag1 126.75(19) . . ?
C7 C2 N1 106.1(2) . . ?
C7 C2 C3 122.0(3) . . ?
N1 C2 C3 131.9(2) . . ?
C4 C3 C2 116.6(3) . . ?
C4 C3 H3 121.7 . . ?
C2 C3 H3 121.7 . . ?
C3 C4 C5 121.7(3) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 116.6(3) . . ?
C5 C6 H6 121.7 . . ?
C7 C6 H6 121.7 . . ?
C2 C7 C6 121.6(2) . . ?
C2 C7 N2 106.4(2) . . ?
C6 C7 N2 132.0(2) . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 C10 112.78(19) . . ?
N2 C9 H9A 109.0 . . ?
C10 C9 H9A 109.0 . . ?
N2 C9 H9B 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 C9 114.9(3) 3_655 . ?
C9 C10 H10A 108.5 3_655 . ?
C9 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 3_655 . ?
C9 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
O2 C11 O1 124.8(3) . . ?
O2 C11 C12 120.4(3) . . ?
O1 C11 C12 114.8(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_refine_diff_density_max         0.673
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.097


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/hexane'
####################################################################### 
# 
# 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_C172
_database_code_depnum_ccdc_archive 'CCDC 1550649'
_audit_update_record             
;
2017-05-17 deposited with the CCDC.
2017-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C23H20F6N4NiO4
_chemical_formula_sum            'C23.50 H22 Cl2.15 F5.50 N4 Ni O3.75'
_chemical_formula_weight         659.88

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.649(6)
_cell_length_b                   10.985(8)
_cell_length_c                   15.733(12)
_cell_angle_alpha                81.770(16)
_cell_angle_beta                 85.099(18)
_cell_angle_gamma                70.204(14)
_cell_volume                     1390.9(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    793
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      20.60

_exptl_crystal_description       Thin_Plate
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_F_000             670
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.977
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.4730
_exptl_absorpt_correction_T_max  0.5630
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14921
_diffrn_reflns_av_unetI/netI     0.0812
_diffrn_reflns_av_R_equivalents  0.0733
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.309
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4896
_reflns_number_gt                3364
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences.
 One of the COOCF3 groups was disordered with 16% replaced 
 by Cl.  
;

_computing_bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'APEX3 v2016.1-0 (Bruker AXS)'
_computing_data_collection       'APEX3 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL--2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXT--(Sheldrick 2015)'
_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)+(0.0834P)²+0.8712P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4896
_refine_ls_number_parameters     382
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.1030
_refine_ls_R_factor_gt           0.0671
_refine_ls_wR_factor_ref         0.1728
_refine_ls_wR_factor_gt          0.1518
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      6.392
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.73560(8) 0.74676(7) 0.72690(5) 0.0301(2) Uani 1 1 d D . . . .
O1 O 0.7776(4) 0.6453(3) 0.6322(3) 0.0357(9) Uani 1 1 d . . . . .
O2 O 0.5407(5) 0.7700(4) 0.5737(3) 0.0415(10) Uani 1 1 d . . . . .
C20 C 0.6678(7) 0.6757(5) 0.5797(4) 0.0330(14) Uani 1 1 d . . . . .
C21 C 0.6987(7) 0.5813(6) 0.5118(5) 0.0448(16) Uani 1 1 d . . . . .
F1 F 0.8418(6) 0.5609(6) 0.4710(4) 0.123(2) Uani 1 1 d . . . . .
F2 F 0.5872(6) 0.6192(4) 0.4528(3) 0.0863(15) Uani 1 1 d . . . . .
F3 F 0.6964(8) 0.4671(4) 0.5468(3) 0.1011(18) Uani 1 1 d . . . . .
O3 O 0.6587(7) 0.6163(4) 0.7903(3) 0.0356(12) Uani 0.843(5) 1 d D . P A 1
O4 O 0.3964(5) 0.7366(4) 0.8108(3) 0.0357(12) Uani 0.843(5) 1 d . . P A 1
C22 C 0.5130(7) 0.6396(8) 0.8153(5) 0.022(3) Uani 0.843(5) 1 d D U P A 1
C23 C 0.4828(8) 0.5085(7) 0.8544(5) 0.0420(19) Uani 0.843(5) 1 d . . P A 1
F4 F 0.4911(8) 0.4332(5) 0.7951(4) 0.091(2) Uani 0.843(5) 1 d . . P A 1
F5 F 0.3390(6) 0.5264(5) 0.8955(4) 0.085(2) Uani 0.843(5) 1 d . . P A 1
F6 F 0.5955(6) 0.4390(5) 0.9095(4) 0.085(2) Uani 0.843(5) 1 d . . P A 1
Cl1X Cl 0.5587(17) 0.6400(10) 0.8089(7) 0.017(3) Uani 0.157(5) 1 d . U P A 2
N1 N 1.0003(5) 0.8408(4) 0.6628(3) 0.0280(10) Uani 1 1 d . . . . .
N2 N 0.7616(5) 0.9878(4) 0.6352(3) 0.0238(9) Uani 1 1 d . . . . .
N3 N 0.5961(5) 0.9629(4) 0.8266(3) 0.0270(10) Uani 1 1 d . . . . .
N4 N 0.8114(5) 0.8192(5) 0.8835(3) 0.0347(11) Uani 1 1 d . . . . .
C1 C 0.8346(6) 0.8623(5) 0.6691(3) 0.0271(12) Uani 1 1 d . . . . .
C2 C 1.0315(6) 0.9530(5) 0.6247(3) 0.0261(12) Uani 1 1 d . . . . .
C3 C 1.1800(6) 0.9766(5) 0.6034(3) 0.0311(13) Uani 1 1 d . . . . .
H3 H 1.2816 0.9138 0.6155 0.037 Uiso 1 1 calc R U . . .
C4 C 1.1645(6) 1.1006(5) 0.5629(3) 0.0315(13) Uani 1 1 d . . . . .
H4 H 1.2594 1.1217 0.5475 0.038 Uiso 1 1 calc R U . . .
C5 C 1.0119(7) 1.1954(5) 0.5441(4) 0.0323(13) Uani 1 1 d . . . . .
H5 H 1.0085 1.2769 0.5164 0.039 Uiso 1 1 calc R U . . .
C6 C 0.8660(6) 1.1707(5) 0.5659(3) 0.0282(12) Uani 1 1 d . . . . .
H6 H 0.7643 1.2335 0.5539 0.034 Uiso 1 1 calc R U . . .
C7 C 0.8802(6) 1.0465(5) 0.6067(3) 0.0234(11) Uani 1 1 d . . . . .
C8 C 1.1274(6) 0.7140(5) 0.6838(4) 0.0388(14) Uani 1 1 d . . . . .
H8A H 1.0763 0.6488 0.7015 0.058 Uiso 1 1 calc R U . . .
H8B H 1.1910 0.7188 0.7295 0.058 Uiso 1 1 calc R U . . .
H8C H 1.1982 0.6913 0.6340 0.058 Uiso 1 1 calc R U . . .
C9 C 0.5857(6) 1.0495(5) 0.6210(3) 0.0271(12) Uani 1 1 d . . . . .
H9A H 0.5408 0.9833 0.6107 0.032 Uiso 1 1 calc R U . . .
H9B H 0.5718 1.1119 0.5696 0.032 Uiso 1 1 calc R U . . .
C10 C 0.4870(6) 1.1195(5) 0.6955(3) 0.0299(12) Uani 1 1 d . . . . .
H10A H 0.5463 1.1707 0.7146 0.036 Uiso 1 1 calc R U . . .
H10B H 0.3826 1.1793 0.6747 0.036 Uiso 1 1 calc R U . . .
C11 C 0.4540(6) 1.0286(5) 0.7722(3) 0.0308(13) Uani 1 1 d . . . . .
H11A H 0.3632 1.0785 0.8071 0.037 Uiso 1 1 calc R U . . .
H11B H 0.4204 0.9629 0.7512 0.037 Uiso 1 1 calc R U . . .
C12 C 0.7086(6) 0.8446(5) 0.8177(4) 0.0323(13) Uani 1 1 d . . . . .
C13 C 0.6278(6) 1.0160(5) 0.8960(4) 0.0318(13) Uani 1 1 d . . . . .
C14 C 0.5495(7) 1.1315(6) 0.9296(4) 0.0375(14) Uani 1 1 d . . . . .
H14 H 0.4567 1.1933 0.9050 0.045 Uiso 1 1 calc R U . . .
C15 C 0.6145(7) 1.1516(6) 1.0015(4) 0.0414(15) Uani 1 1 d . . . . .
H15 H 0.5658 1.2293 1.0252 0.050 Uiso 1 1 calc R U . . .
C16 C 0.7515(7) 1.0580(7) 1.0390(4) 0.0418(16) Uani 1 1 d . . . . .
H16 H 0.7911 1.0743 1.0878 0.050 Uiso 1 1 calc R U . . .
C17 C 0.8313(7) 0.9409(6) 1.0062(4) 0.0399(15) Uani 1 1 d . . . . .
H17 H 0.9235 0.8787 1.0311 0.048 Uiso 1 1 calc R U . . .
C18 C 0.7652(7) 0.9226(6) 0.9341(4) 0.0339(13) Uani 1 1 d . . . . .
C19 C 0.9518(8) 0.7003(6) 0.9015(4) 0.0472(16) Uani 1 1 d . . . . .
H19A H 0.9506 0.6373 0.8654 0.071 Uiso 1 1 calc R U . . .
H19B H 0.9450 0.6654 0.9607 0.071 Uiso 1 1 calc R U . . .
H19C H 1.0520 0.7203 0.8904 0.071 Uiso 1 1 calc R U . . .
C1S C 0.9418(8) 0.3368(6) 0.7496(4) 0.0492(16) Uani 1 1 d . . . . .
H1S1 H 0.8393 0.4076 0.7561 0.059 Uiso 1 1 calc R U . . .
H1S2 H 0.9672 0.3327 0.6886 0.059 Uiso 1 1 calc R U . . .
Cl1 Cl 1.1016(2) 0.36985(17) 0.79650(13) 0.0589(5) Uani 1 1 d D . . . .
Cl2 Cl 0.9172(2) 0.19021(17) 0.79698(12) 0.0611(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 C1 1.856(5) . ?
Ni1 C12 1.861(6) . ?
Ni1 O3 1.901(4) . ?
Ni1 O1 1.924(4) . ?
Ni1 Cl1X 2.414(13) . ?
O1 C20 1.239(7) . ?
O2 C20 1.229(6) . ?
C20 C21 1.540(9) . ?
C21 F3 1.302(7) . ?
C21 F1 1.309(7) . ?
C21 F2 1.318(7) . ?
O3 C22 1.238(2) . ?
O4 C22 1.191(8) . ?
C22 C23 1.580(11) . ?
C23 F4 1.315(9) . ?
C23 F5 1.317(8) . ?
C23 F6 1.318(8) . ?
N1 C1 1.369(6) . ?
N1 C2 1.392(6) . ?
N1 C8 1.466(6) . ?
N2 C1 1.357(6) . ?
N2 C7 1.399(6) . ?
N2 C9 1.463(6) . ?
N3 C12 1.353(7) . ?
N3 C13 1.395(7) . ?
N3 C11 1.472(6) . ?
N4 C12 1.358(7) . ?
N4 C18 1.407(7) . ?
N4 C19 1.462(7) . ?
C2 C7 1.385(7) . ?
C2 C3 1.399(7) . ?
C3 C4 1.387(7) . ?
C4 C5 1.401(8) . ?
C5 C6 1.383(7) . ?
C6 C7 1.393(7) . ?
C9 C10 1.528(7) . ?
C10 C11 1.524(7) . ?
C13 C14 1.378(8) . ?
C13 C18 1.394(8) . ?
C14 C15 1.382(8) . ?
C15 C16 1.389(9) . ?
C16 C17 1.387(9) . ?
C17 C18 1.382(8) . ?
C1S Cl2 1.748(7) . ?
C1S Cl1 1.782(7) . ?

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
C1 Ni1 C12 84.7(2) . . ?
C1 Ni1 O3 173.4(2) . . ?
C12 Ni1 O3 95.3(2) . . ?
C1 Ni1 O1 92.9(2) . . ?
C12 Ni1 O1 176.41(19) . . ?
O3 Ni1 O1 86.8(2) . . ?
C1 Ni1 Cl1X 167.3(3) . . ?
C12 Ni1 Cl1X 87.2(3) . . ?
O1 Ni1 Cl1X 95.7(3) . . ?
C20 O1 Ni1 116.6(4) . . ?
O2 C20 O1 129.5(6) . . ?
O2 C20 C21 116.2(5) . . ?
O1 C20 C21 114.3(5) . . ?
F3 C21 F1 105.8(6) . . ?
F3 C21 F2 105.3(5) . . ?
F1 C21 F2 106.7(6) . . ?
F3 C21 C20 111.2(6) . . ?
F1 C21 C20 113.3(5) . . ?
F2 C21 C20 113.8(5) . . ?
C22 O3 Ni1 121.9(5) . . ?
O4 C22 O3 132.9(8) . . ?
O4 C22 C23 117.2(6) . . ?
O3 C22 C23 109.7(6) . . ?
F4 C23 F5 106.9(6) . . ?
F4 C23 F6 105.8(7) . . ?
F5 C23 F6 106.7(6) . . ?
F4 C23 C22 112.1(6) . . ?
F5 C23 C22 113.5(6) . . ?
F6 C23 C22 111.3(6) . . ?
C1 N1 C2 110.2(4) . . ?
C1 N1 C8 124.9(4) . . ?
C2 N1 C8 124.5(4) . . ?
C1 N2 C7 110.4(4) . . ?
C1 N2 C9 125.2(4) . . ?
C7 N2 C9 124.0(4) . . ?
C12 N3 C13 111.7(5) . . ?
C12 N3 C11 125.2(5) . . ?
C13 N3 C11 123.1(4) . . ?
C12 N4 C18 111.2(5) . . ?
C12 N4 C19 125.5(5) . . ?
C18 N4 C19 123.2(5) . . ?
N2 C1 N1 106.3(4) . . ?
N2 C1 Ni1 128.2(4) . . ?
N1 C1 Ni1 125.1(4) . . ?
C7 C2 N1 106.7(4) . . ?
C7 C2 C3 122.5(5) . . ?
N1 C2 C3 130.8(5) . . ?
C4 C3 C2 115.0(5) . . ?
C3 C4 C5 122.7(5) . . ?
C6 C5 C4 121.6(5) . . ?
C5 C6 C7 116.2(5) . . ?
C2 C7 C6 122.0(4) . . ?
C2 C7 N2 106.4(4) . . ?
C6 C7 N2 131.6(5) . . ?
N2 C9 C10 114.3(4) . . ?
C11 C10 C9 114.2(4) . . ?
N3 C11 C10 114.1(4) . . ?
N3 C12 N4 105.4(5) . . ?
N3 C12 Ni1 127.5(4) . . ?
N4 C12 Ni1 126.6(4) . . ?
C14 C13 C18 121.1(6) . . ?
C14 C13 N3 132.8(5) . . ?
C18 C13 N3 106.0(5) . . ?
C13 C14 C15 117.3(6) . . ?
C14 C15 C16 121.1(6) . . ?
C15 C16 C17 122.3(6) . . ?
C18 C17 C16 115.8(6) . . ?
C17 C18 C13 122.3(6) . . ?
C17 C18 N4 132.1(6) . . ?
C13 C18 N4 105.6(5) . . ?
Cl2 C1S Cl1 112.0(4) . . ?

_refine_diff_density_max         0.704
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.099


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/hexane'
