# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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_eva789a
_database_code_depnum_ccdc_archive 'CCDC 1962312'
loop_
_audit_author_name
_audit_author_address
'galina starova'
;Saint Petersburg state university
Russia
;
_audit_update_record             
;
2019-10-29 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_audit_creation_date             2019-10-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H32 N8 Ni O2, 2(C F3 O3 S)'
_chemical_formula_sum            'C18 H32 F6 N8 Ni O8 S2'
_chemical_formula_weight         725.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         'ni1 h20  S2 N10  C20 f6 o6'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8741(5)
_cell_length_b                   9.1095(6)
_cell_length_c                   11.9118(7)
_cell_angle_alpha                102.589(6)
_cell_angle_beta                 108.164(6)
_cell_angle_gamma                96.805(5)
_cell_volume                     776.15(9)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2833
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.7390
_cell_measurement_theta_min      5.0120
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.982
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       tables
_exptl_crystal_F_000             374
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5217
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.994
_diffrn_reflns_theta_min         4.057
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -102.00  -39.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -38.0000  -60.0000 63

#__ type_ start__ end____ width___ exp.time_
  2 omega  -34.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000 -150.0000 58

#__ type_ start__ end____ width___ exp.time_
  3 omega  -61.00  -21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -38.0000  -30.0000 40

#__ type_ start__ end____ width___ exp.time_
  4 omega  -43.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  120.0000 79

#__ type_ start__ end____ width___ exp.time_
  5 omega -130.00  -38.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787 -178.0000  150.0000 92

#__ type_ start__ end____ width___ exp.time_
  6 omega   36.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  -99.0000  120.0000 39

#__ type_ start__ end____ width___ exp.time_
  7 omega   62.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -60.0000 50

#__ type_ start__ end____ width___ exp.time_
  8 omega  139.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  120.0000 39

#__ type_ start__ end____ width___ exp.time_
  9 omega   64.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   82.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  120.0000 32

#__ type_ start__ end____ width___ exp.time_
 11 omega   36.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -30.0000 41

#__ type_ start__ end____ width___ exp.time_
 12 omega   65.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -180.0000 47

#__ type_ start__ end____ width___ exp.time_
 13 omega   67.00   95.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -150.0000 28

#__ type_ start__ end____ width___ exp.time_
 14 omega   43.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   90.0000 53

#__ type_ start__ end____ width___ exp.time_
 15 omega   48.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -150.0000 41

#__ type_ start__ end____ width___ exp.time_
 16 omega   45.00   94.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  120.0000 49

#__ type_ start__ end____ width___ exp.time_
 17 omega   58.00  131.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  150.0000 73

#__ type_ start__ end____ width___ exp.time_
 18 omega   45.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -90.0000 32

#__ type_ start__ end____ width___ exp.time_
 19 omega  109.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega  148.00  174.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 21 omega  114.00  140.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 22 omega   59.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   30.0000 56

#__ type_ start__ end____ width___ exp.time_
 23 omega   35.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -60.0000 36

#__ type_ start__ end____ width___ exp.time_
 24 omega   39.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -180.0000 50

#__ type_ start__ end____ width___ exp.time_
 25 omega   89.00  164.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000 -150.0000 75
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1027598000
_diffrn_orient_matrix_UB_12      0.1324648000
_diffrn_orient_matrix_UB_13      -0.0139371000
_diffrn_orient_matrix_UB_21      0.1348814000
_diffrn_orient_matrix_UB_22      0.0691468000
_diffrn_orient_matrix_UB_23      -0.0536526000
_diffrn_orient_matrix_UB_31      -0.1242288000
_diffrn_orient_matrix_UB_32      -0.0946740000
_diffrn_orient_matrix_UB_33      -0.1300489000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2499
_reflns_number_total             2842
_reflns_odcompleteness_completeness 96.30
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2842
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0354
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0470P)²+0.3518P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0928
_refine_special_details          ?
_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 C(H,H,H) groups
2. Restrained distances
 H1A-O1
 0.85 with sigma of 0.02
 H1B-O1
 0.85 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 N4(H4), C5(H5)
3.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C3(H3A,H3B,H3C), C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.000000 0.500000 0.000000 0.01248(14) Uani 1 2 d S T P . .
S1 S 0.62196(6) 0.82723(6) 0.23299(4) 0.01626(14) Uani 1 1 d . . . . .
O1 O 0.2708(2) 0.47352(17) 0.03374(13) 0.0181(3) Uani 1 1 d D . . . .
F1 F 0.94784(18) 0.79200(18) 0.35131(14) 0.0352(4) Uani 1 1 d . . . . .
F2 F 0.8104(2) 0.9026(3) 0.46589(14) 0.0652(7) Uani 1 1 d . . . . .
O3 O 0.7103(2) 0.9655(2) 0.21964(19) 0.0386(5) Uani 1 1 d . . . . .
O4 O 0.4634(2) 0.83697(17) 0.26802(14) 0.0217(3) Uani 1 1 d . . . . .
F3 F 0.7285(3) 0.6592(3) 0.3816(2) 0.0667(7) Uani 1 1 d . . . . .
N3 N 0.0390(2) 0.50428(19) 0.18215(15) 0.0158(4) Uani 1 1 d . . . . .
C9 C 0.7867(3) 0.7939(3) 0.3653(2) 0.0309(6) Uani 1 1 d . . . . .
N4 N 0.1930(2) 0.5930(2) 0.27230(15) 0.0167(4) Uani 1 1 d . . . . .
H4 H 0.272439 0.658126 0.259785 0.020 Uiso 1 1 calc R . . . .
O2 O 0.5971(2) 0.6912(2) 0.13586(17) 0.0401(5) Uani 1 1 d . . . . .
N1 N 0.0694(2) 0.73692(19) 0.05597(15) 0.0170(4) Uani 1 1 d . . . . .
N2 N 0.1671(2) 1.0185(2) 0.13676(16) 0.0192(4) Uani 1 1 d . . . . .
C1 C 0.1186(3) 0.8676(2) 0.09490(18) 0.0158(4) Uani 1 1 d . . . . .
C6 C 0.2100(3) 0.5697(2) 0.38249(19) 0.0195(4) Uani 1 1 d . . . . .
C5 C 0.0617(3) 0.4587(2) 0.3636(2) 0.0211(5) Uani 1 1 d . . . . .
H5 H 0.035495 0.415262 0.423491 0.025 Uiso 1 1 calc R . . . .
C7 C 0.3616(3) 0.6622(3) 0.4968(2) 0.0290(5) Uani 1 1 d . . . . .
H7A H 0.473835 0.682086 0.478481 0.043 Uiso 1 1 calc GR . . . .
H7B H 0.380757 0.605202 0.559125 0.043 Uiso 1 1 calc GR . . . .
H7C H 0.329659 0.760002 0.527711 0.043 Uiso 1 1 calc GR . . . .
C4 C -0.0431(3) 0.4224(2) 0.23846(19) 0.0180(4) Uani 1 1 d . . . . .
C8 C -0.2242(3) 0.3156(3) 0.1735(2) 0.0270(5) Uani 1 1 d . . . . .
H8A H -0.318247 0.362581 0.196900 0.040 Uiso 1 1 calc GR . . . .
H8B H -0.219501 0.218796 0.196426 0.040 Uiso 1 1 calc GR . . . .
H8C H -0.253659 0.295545 0.084648 0.040 Uiso 1 1 calc GR . . . .
C3 C 0.1842(3) 1.0848(3) 0.2650(2) 0.0292(5) Uani 1 1 d . . . . .
H3A H 0.083339 1.031599 0.282118 0.044 Uiso 1 1 calc GR . . . .
H3B H 0.180200 1.194160 0.278228 0.044 Uiso 1 1 calc GR . . . .
H3C H 0.300482 1.072775 0.319959 0.044 Uiso 1 1 calc GR . . . .
C2 C 0.2939(3) 1.0967(3) 0.0907(2) 0.0282(5) Uani 1 1 d . . . . .
H2A H 0.418807 1.089279 0.135359 0.042 Uiso 1 1 calc GR . . . .
H2B H 0.284832 1.205028 0.102917 0.042 Uiso 1 1 calc GR . . . .
H2C H 0.262795 1.048101 0.002998 0.042 Uiso 1 1 calc GR . . . .
H1A H 0.363(3) 0.544(3) 0.069(3) 0.039(8) Uiso 1 1 d D . . . .
H1B H 0.296(4) 0.419(3) -0.024(2) 0.034(8) 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
Ni1 O1 2.0964(15) 2_565 ?
Ni1 O1 2.0964(15) . ?
Ni1 N3 2.0853(17) 2_565 ?
Ni1 N3 2.0853(17) . ?
Ni1 N1 2.0657(17) . ?
Ni1 N1 2.0657(17) 2_565 ?
S1 O3 1.4298(17) . ?
S1 O4 1.4410(16) . ?
S1 C9 1.813(2) . ?
S1 O2 1.4456(17) . ?
O1 H1A 0.839(17) . ?
O1 H1B 0.842(17) . ?
F1 C9 1.332(3) . ?
F2 C9 1.323(3) . ?
F3 C9 1.334(3) . ?
N3 N4 1.362(2) . ?
N3 C4 1.341(3) . ?
N4 H4 0.8800 . ?
N4 C6 1.343(3) . ?
N1 C1 1.149(3) . ?
N2 C1 1.320(3) . ?
N2 C3 1.472(3) . ?
N2 C2 1.466(3) . ?
C6 C5 1.377(3) . ?
C6 C7 1.496(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.402(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C4 C8 1.494(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 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
O1 Ni1 O1 180.0 . 2_565 ?
N3 Ni1 O1 88.09(6) . . ?
N3 Ni1 O1 91.91(6) . 2_565 ?
N3 Ni1 O1 88.09(6) 2_565 2_565 ?
N3 Ni1 O1 91.91(6) 2_565 . ?
N3 Ni1 N3 180.0 . 2_565 ?
N1 Ni1 O1 86.25(6) . 2_565 ?
N1 Ni1 O1 93.75(6) 2_565 2_565 ?
N1 Ni1 O1 86.25(6) 2_565 . ?
N1 Ni1 O1 93.75(6) . . ?
N1 Ni1 N3 87.90(7) 2_565 2_565 ?
N1 Ni1 N3 87.90(7) . . ?
N1 Ni1 N3 92.10(7) 2_565 . ?
N1 Ni1 N3 92.10(7) . 2_565 ?
N1 Ni1 N1 180.0 . 2_565 ?
O3 S1 O4 116.15(11) . . ?
O3 S1 C9 103.84(12) . . ?
O3 S1 O2 114.77(13) . . ?
O4 S1 C9 103.41(10) . . ?
O4 S1 O2 113.18(10) . . ?
O2 S1 C9 103.33(13) . . ?
Ni1 O1 H1A 125(2) . . ?
Ni1 O1 H1B 118(2) . . ?
H1A O1 H1B 103(3) . . ?
N4 N3 Ni1 119.18(13) . . ?
C4 N3 Ni1 135.02(14) . . ?
C4 N3 N4 105.17(16) . . ?
F1 C9 S1 111.27(17) . . ?
F1 C9 F3 108.1(2) . . ?
F2 C9 S1 110.71(18) . . ?
F2 C9 F1 108.3(2) . . ?
F2 C9 F3 108.1(2) . . ?
F3 C9 S1 110.27(18) . . ?
N3 N4 H4 123.8 . . ?
C6 N4 N3 112.35(17) . . ?
C6 N4 H4 123.8 . . ?
C1 N1 Ni1 174.64(16) . . ?
C1 N2 C3 116.54(19) . . ?
C1 N2 C2 117.34(19) . . ?
C2 N2 C3 116.82(18) . . ?
N1 C1 N2 177.2(2) . . ?
N4 C6 C5 106.21(18) . . ?
N4 C6 C7 121.9(2) . . ?
C5 C6 C7 131.8(2) . . ?
C6 C5 H5 126.8 . . ?
C6 C5 C4 106.33(19) . . ?
C4 C5 H5 126.8 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C4 C5 109.92(19) . . ?
N3 C4 C8 122.82(19) . . ?
C5 C4 C8 127.2(2) . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 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
Ni1 N3 N4 C6 -172.30(14) . . . . ?
Ni1 N3 C4 C5 169.52(16) . . . . ?
Ni1 N3 C4 C8 -13.2(3) . . . . ?
O3 S1 C9 F1 -54.2(2) . . . . ?
O3 S1 C9 F2 66.3(2) . . . . ?
O3 S1 C9 F3 -174.16(19) . . . . ?
O4 S1 C9 F1 -175.86(17) . . . . ?
O4 S1 C9 F2 -55.4(2) . . . . ?
O4 S1 C9 F3 64.1(2) . . . . ?
N3 N4 C6 C5 1.0(2) . . . . ?
N3 N4 C6 C7 -175.6(2) . . . . ?
N4 N3 C4 C5 -0.9(2) . . . . ?
N4 N3 C4 C8 176.4(2) . . . . ?
N4 C6 C5 C4 -1.4(2) . . . . ?
O2 S1 C9 F1 66.0(2) . . . . ?
O2 S1 C9 F2 -173.62(19) . . . . ?
O2 S1 C9 F3 -54.0(2) . . . . ?
C6 C5 C4 N3 1.5(3) . . . . ?
C6 C5 C4 C8 -175.6(2) . . . . ?
C7 C6 C5 C4 174.7(2) . . . . ?
C4 N3 N4 C6 -0.1(2) . . . . ?

_olex2_date_sample_data_collection 1454499227.21
_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_m10
_database_code_depnum_ccdc_archive 'CCDC 1966455'
_audit_update_record             
;
2019-11-18 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_audit_creation_date             2019-11-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H28 N12 Ni, 2(N O3)'
_chemical_formula_sum            'C18 H28 N14 Ni O6'
_chemical_formula_weight         595.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Ni C27'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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 1 21/n 1'
_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                   9.6235(7)
_cell_length_b                   8.0534(5)
_cell_length_c                   16.8565(12)
_cell_angle_alpha                90
_cell_angle_beta                 103.297(7)
_cell_angle_gamma                90
_cell_volume                     1271.39(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2277
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.7780
_cell_measurement_theta_min      4.8610
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.674
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6439
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.986
_diffrn_reflns_theta_min         4.869
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -104.00 -71.00   0.50    4.00    --  -41.10 -70.00-121.00   66
  2  ω    -56.00  22.00   0.50    4.00    --  -41.10  70.00   9.00  156
  3  ω    -61.00 -35.00   0.50    4.00    --  -41.10 -70.00-121.00   52
  4  ω     11.00  51.00   0.50    4.00    --   41.10 -70.00-121.00   80
  5  ω     65.00 112.00   0.50    9.40    --  101.00 -70.00-121.00   94
  6  ω     95.00 157.00   0.50    9.40    --  101.00  70.00   9.00  124
  7  ω    -50.00  -4.00   0.50    4.00    --  -41.10  32.00   0.00   92
  8  ω    -67.00 -34.00   0.50    4.00    --  -41.10 -32.00  90.00   66
  9  ω   -107.00 -72.00   0.50    4.00    --  -41.10 -32.00  90.00   70
 10  ω    -51.00  16.00   0.50    4.00    --  -41.10  21.00 -60.00  134
 11  ω   -109.00 -33.00   0.50    4.00    --  -41.10 -21.00 120.00  152
 12  ω     60.00  96.00   0.50    4.00    --   41.10  70.00   9.00   72
 13  ω     22.00  47.00   0.50    4.00    --   41.10  70.00   9.00   50
 14  ω    -12.00  33.00   0.50    4.00    --   41.10 -54.00 120.00   90
 15  ω     54.00  79.00   0.50    4.00    --   41.10  32.00   0.00   50
 16  ω     54.00 114.00   0.50    9.40    --  101.00 -42.00-150.00  120
 17  ω     68.00 105.00   0.50    9.40    --  101.00 -42.00 150.00   74
 18  ω     79.00 109.00   0.50    9.40    --  101.00 -77.00 120.00   60
 19  ω     92.00 124.00   0.50    9.40    --  101.00  33.00  30.00   64
 20  ω     84.00 116.00   0.50    9.40    --  101.00  59.00 120.00   64
 21  ω     94.00 152.00   0.50    9.40    --  101.00 111.00 -90.00  116
 22  ω     82.00 153.00   0.50    9.40    --  101.00 111.00 -60.00  142
 23  ω    132.00 157.00   0.50    9.40    --  101.00  77.00 -60.00   50
 24  ω     77.00 113.00   0.50    9.40    --  101.00  77.00 -60.00   72
 25  ω    100.00 157.00   0.50    9.40    --  101.00  25.00 -30.00  114
 26  ω     38.00  86.00   0.50    9.40    --  101.00 -50.00 -60.00   96
 27  ω    103.00 153.00   0.50    9.40    --  101.00  42.00  60.00  100
 28  ω     43.00  69.00   0.50    9.40    --  101.00 -77.00 120.00   52
 29  ω     30.00  61.00   0.50    9.40    --  101.00 -17.00  30.00   62
 30  ω     98.00 133.00   0.50    9.40    --  101.00  93.00 -30.00   70
 31  ω     38.00  93.00   0.50    9.40    --  101.00 -68.00-150.00  110
 32  ω    132.00 157.00   0.50    9.40    --  101.00  33.00-150.00   50
 33  ω     93.00 118.00   0.50    9.40    --  101.00  33.00-150.00   50
 34  ω     98.00 156.00   0.50    9.40    --  101.00  25.00 -60.00  116
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1099903000
_diffrn_orient_matrix_UB_12      0.0854282000
_diffrn_orient_matrix_UB_13      -0.0688782000
_diffrn_orient_matrix_UB_21      0.0338483000
_diffrn_orient_matrix_UB_22      -0.1258890000
_diffrn_orient_matrix_UB_23      -0.0617494000
_diffrn_orient_matrix_UB_31      -0.1174971000
_diffrn_orient_matrix_UB_32      -0.1159151000
_diffrn_orient_matrix_UB_33      0.0163989000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2088
_reflns_number_total             2399
_reflns_odcompleteness_completeness 98.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2399
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0413
_refine_ls_restrained_S_all      1.082
_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)+(0.0305P)²+1.3880P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.0932
_refine_special_details          ?
_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 C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N6(H6), C5(H5), C6(H6A), C4(H4), C7(H7), C9(H9), C8(H8)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.500000 0.500000 0.500000 0.01998(16) Uani 1 2 d S T P . .
O1 O 0.93532(18) 0.4810(2) 0.60037(12) 0.0334(4) Uani 1 1 d . . . . .
O2 O 1.14671(17) 0.3911(2) 0.59706(12) 0.0354(4) Uani 1 1 d . . . . .
O3 O 0.99066(19) 0.2243(2) 0.62787(13) 0.0376(5) Uani 1 1 d . . . . .
N4 N 0.60342(19) 0.7150(2) 0.54629(12) 0.0209(4) Uani 1 1 d . . . . .
N3 N 0.51606(19) 0.8200(2) 0.57710(11) 0.0202(4) Uani 1 1 d . . . . .
N1 N 0.33794(19) 0.6294(2) 0.53423(12) 0.0215(4) Uani 1 1 d . . . . .
H1 H 0.250989 0.595123 0.522254 0.026 Uiso 1 1 calc R . . . .
N7 N 1.0247(2) 0.3650(2) 0.60789(12) 0.0239(4) Uani 1 1 d . . . . .
N5 N 0.55986(19) 0.3994(2) 0.61980(12) 0.0223(4) Uani 1 1 d . . . . .
N6 N 0.69671(19) 0.3563(2) 0.65345(12) 0.0230(4) Uani 1 1 d . . . . .
H6 H 0.766838 0.371636 0.630549 0.028 Uiso 1 1 calc R . . . .
N2 N 0.2932(2) 0.8643(2) 0.61016(12) 0.0233(4) Uani 1 1 d . . . . .
C1 C 0.3743(2) 0.7637(3) 0.57431(14) 0.0207(5) Uani 1 1 d . . . . .
C5 C 0.7104(2) 0.9628(3) 0.57644(14) 0.0219(5) Uani 1 1 d . . . . .
H5 H 0.779132 1.045935 0.583015 0.026 Uiso 1 1 calc R . . . .
C6 C 0.7201(2) 0.8012(3) 0.54666(14) 0.0232(5) Uani 1 1 d . . . . .
H6A H 0.798679 0.760414 0.529436 0.028 Uiso 1 1 calc R . . . .
C4 C 0.5788(2) 0.9720(3) 0.59367(13) 0.0220(5) Uani 1 1 d . . . . .
H4 H 0.539269 1.064535 0.613090 0.026 Uiso 1 1 calc R . . . .
C7 C 0.4865(3) 0.3552(3) 0.67493(15) 0.0268(5) Uani 1 1 d . . . . .
H7 H 0.388712 0.370270 0.668583 0.032 Uiso 1 1 calc R . . . .
C9 C 0.7091(3) 0.2868(3) 0.72689(15) 0.0274(5) Uani 1 1 d . . . . .
H9 H 0.792995 0.247814 0.760758 0.033 Uiso 1 1 calc R . . . .
C8 C 0.5763(3) 0.2833(3) 0.74328(15) 0.0291(5) Uani 1 1 d . . . . .
H8 H 0.551350 0.242253 0.789674 0.035 Uiso 1 1 calc R . . . .
C2 C 0.1384(2) 0.8360(3) 0.58740(17) 0.0306(6) Uani 1 1 d . . . . .
H2A H 0.108059 0.825190 0.529264 0.046 Uiso 1 1 calc GR . . . .
H2B H 0.090137 0.928165 0.605203 0.046 Uiso 1 1 calc GR . . . .
H2C H 0.115901 0.736032 0.612851 0.046 Uiso 1 1 calc GR . . . .
C3 C 0.3429(3) 0.9264(4) 0.69345(16) 0.0345(6) Uani 1 1 d . . . . .
H3A H 0.308474 0.855361 0.730441 0.052 Uiso 1 1 calc GR . . . .
H3B H 0.307550 1.037025 0.696914 0.052 Uiso 1 1 calc GR . . . .
H3C H 0.445425 0.927732 0.707633 0.052 Uiso 1 1 calc GR . . . .


_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 N4 2.0593(18) . ?
Ni1 N4 2.0593(18) 3_666 ?
Ni1 N1 2.0654(18) . ?
Ni1 N1 2.0655(18) 3_666 ?
Ni1 N5 2.1287(19) 3_666 ?
Ni1 N5 2.1288(19) . ?
O1 N7 1.256(3) . ?
O2 N7 1.247(2) . ?
O3 N7 1.247(3) . ?
N4 N3 1.376(3) . ?
N4 C6 1.319(3) . ?
N3 C1 1.428(3) . ?
N3 C4 1.365(3) . ?
N1 H1 0.8600 . ?
N1 C1 1.281(3) . ?
N5 N6 1.354(3) . ?
N5 C7 1.338(3) . ?
N6 H6 0.8600 . ?
N6 C9 1.339(3) . ?
N2 C1 1.359(3) . ?
N2 C2 1.467(3) . ?
N2 C3 1.464(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.405(3) . ?
C5 C4 1.365(3) . ?
C6 H6A 0.9300 . ?
C4 H4 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.397(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.368(3) . ?
C8 H8 0.9300 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 Ni1 N4 180.0 . 3_666 ?
N4 Ni1 N1 101.54(7) . 3_666 ?
N4 Ni1 N1 78.46(7) . . ?
N4 Ni1 N1 78.46(7) 3_666 3_666 ?
N4 Ni1 N1 101.54(7) 3_666 . ?
N4 Ni1 N5 92.35(7) . 3_666 ?
N4 Ni1 N5 87.65(7) . . ?
N4 Ni1 N5 87.65(7) 3_666 3_666 ?
N4 Ni1 N5 92.35(7) 3_666 . ?
N1 Ni1 N1 180.0 . 3_666 ?
N1 Ni1 N5 89.09(7) . . ?
N1 Ni1 N5 90.91(7) . 3_666 ?
N1 Ni1 N5 89.09(7) 3_666 3_666 ?
N1 Ni1 N5 90.91(7) 3_666 . ?
N5 Ni1 N5 180.00(10) 3_666 . ?
N3 N4 Ni1 112.08(13) . . ?
C6 N4 Ni1 141.36(16) . . ?
C6 N4 N3 105.55(18) . . ?
N4 N3 C1 117.03(17) . . ?
C4 N3 N4 110.39(18) . . ?
C4 N3 C1 131.74(19) . . ?
Ni1 N1 H1 121.9 . . ?
C1 N1 Ni1 116.17(15) . . ?
C1 N1 H1 121.9 . . ?
O2 N7 O1 120.4(2) . . ?
O2 N7 O3 120.5(2) . . ?
O3 N7 O1 119.09(19) . . ?
N6 N5 Ni1 121.33(15) . . ?
C7 N5 Ni1 133.56(16) . . ?
C7 N5 N6 105.00(19) . . ?
N5 N6 H6 124.3 . . ?
C9 N6 N5 111.43(19) . . ?
C9 N6 H6 124.3 . . ?
C1 N2 C2 116.34(19) . . ?
C1 N2 C3 122.4(2) . . ?
C3 N2 C2 113.10(19) . . ?
N1 C1 N3 115.4(2) . . ?
N1 C1 N2 128.5(2) . . ?
N2 C1 N3 116.02(19) . . ?
C6 C5 H5 127.2 . . ?
C4 C5 H5 127.2 . . ?
C4 C5 C6 105.5(2) . . ?
N4 C6 C5 111.2(2) . . ?
N4 C6 H6A 124.4 . . ?
C5 C6 H6A 124.4 . . ?
N3 C4 H4 126.4 . . ?
C5 C4 N3 107.23(19) . . ?
C5 C4 H4 126.4 . . ?
N5 C7 H7 124.5 . . ?
N5 C7 C8 111.0(2) . . ?
C8 C7 H7 124.5 . . ?
N6 C9 H9 126.1 . . ?
N6 C9 C8 107.9(2) . . ?
C8 C9 H9 126.1 . . ?
C7 C8 H8 127.6 . . ?
C9 C8 C7 104.7(2) . . ?
C9 C8 H8 127.6 . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.593
_oxdiff_exptl_absorpt_empirical_full_min 0.699
####################################################################### 
# 
# 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_0m05
_database_code_depnum_ccdc_archive 'CCDC 1966457'
loop_
_audit_author_name
_audit_author_address
'Avdontceva Margarita'
;St Petersburg State University
Russia
;
_audit_update_record             
;
2020-03-10 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_audit_creation_date             2019-11-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H36 N12 Ni, 2(C F3 O3 S)'
_chemical_formula_sum            'C24 H36 F6 N12 Ni O6 S2'
_chemical_formula_weight         825.48
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 N12 O6 F6 Ni'
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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6380(6)
_cell_length_b                   10.2071(9)
_cell_length_c                   10.3141(9)
_cell_angle_alpha                101.057(8)
_cell_angle_beta                 101.885(6)
_cell_angle_gamma                111.644(7)
_cell_volume                     882.01(13)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4746
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.1560
_cell_measurement_theta_min      3.7170
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.756
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66592
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             426
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15571
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         3.222
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -13.00  14.00   1.00   32.19    --  -14.18 -57.00   0.00   27
  2  ω    -11.00  15.00   1.00   32.19    --  -14.18 -99.00 -60.00   26
  3  ω    -82.00 -55.00   1.00   32.19    --  -14.18 -57.00   0.00   27
  4  ω    -55.00  43.00   1.00   32.19    --   16.06 -57.00 150.00   98
  5  ω    -11.00  74.00   1.00   32.19    --   16.06  57.00  90.00   85
  6  ω     -8.00  85.00   1.00   32.19    --   16.06  57.00 -60.00   93
  7  ω    -42.00   1.00   1.00   32.19    --  -14.18 -38.00 120.00   43
  8  ω    -42.00   2.00   1.00   32.19    --   16.06 -77.00 -90.00   44
  9  ω     13.00  80.00   1.00   32.19    --   16.06  38.00-180.00   67
 10  ω    -57.00  39.00   1.00   32.19    --   16.06 -38.00   0.00   96
 11  ω      1.00  72.00   1.00   32.19    --   18.00-121.00  98.34   71
 12  ω     20.00  85.00   1.00   32.19    --   18.00-142.00 -25.42   65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0047922000
_diffrn_orient_matrix_UB_12      -0.0171285000
_diffrn_orient_matrix_UB_13      -0.0712203000
_diffrn_orient_matrix_UB_21      -0.0536746000
_diffrn_orient_matrix_UB_22      -0.0736368000
_diffrn_orient_matrix_UB_23      -0.0105160000
_diffrn_orient_matrix_UB_31      -0.0632458000
_diffrn_orient_matrix_UB_32      0.0200955000
_diffrn_orient_matrix_UB_33      -0.0149795000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3326
_reflns_number_total             4053
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.64
_reflns_special_details          
#The highest value of residual electron density refers to heavy atom#
;
 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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.127
_refine_diff_density_min         -0.990
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         4053
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0545
_refine_ls_restrained_S_all      1.068
_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)+(0.0709P)²+1.0544P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1487
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), N6(H6), C6(H6A), C4(H4), C5(H5), C9(H9), C8(H8)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.500000 0.500000 0.500000 0.01962(16) Uani 1 2 d S T P . .
S1 S 0.28119(8) 0.88361(9) 0.27266(8) 0.0264(2) Uani 1 1 d . . . . .
F2 F 0.4790(2) 0.9993(2) 0.1423(2) 0.0418(5) Uani 1 1 d . . . . .
F1 F 0.2947(2) 0.7865(3) 0.0228(2) 0.0468(6) Uani 1 1 d . . . . .
F3 F 0.2467(2) 0.9775(3) 0.0551(2) 0.0447(5) Uani 1 1 d . . . . .
O1 O 0.3879(3) 0.8258(3) 0.3300(2) 0.0343(5) Uani 1 1 d . . . . .
N5 N 0.3080(3) 0.4167(3) 0.3202(3) 0.0248(5) Uani 1 1 d . . . . .
O3 O 0.1190(3) 0.7795(3) 0.2223(3) 0.0441(6) Uani 1 1 d . . . . .
N3 N 0.7225(3) 0.5452(3) 0.3490(2) 0.0221(5) Uani 1 1 d . . . . .
O2 O 0.3143(3) 1.0310(3) 0.3504(3) 0.0434(6) Uani 1 1 d . . . . .
N1 N 0.6061(3) 0.6827(3) 0.4394(2) 0.0221(5) Uani 1 1 d . . . . .
H1 H 0.593571 0.761917 0.464274 0.027 Uiso 1 1 calc R . . . .
N4 N 0.6306(3) 0.4303(3) 0.3875(2) 0.0228(5) Uani 1 1 d . . . . .
N2 N 0.7645(3) 0.7681(3) 0.2978(3) 0.0266(5) Uani 1 1 d . . . . .
C7 C 0.2275(4) 0.2737(4) 0.2484(3) 0.0313(7) Uani 1 1 d . . . . .
H7 H 0.246838 0.197029 0.271605 0.038 Uiso 1 1 calc R . . . .
N6 N 0.2458(4) 0.4921(4) 0.2519(3) 0.0429(8) Uani 1 1 d . . . . .
H6 H 0.277630 0.586311 0.276429 0.051 Uiso 1 1 calc R . . . .
C1 C 0.6921(3) 0.6714(3) 0.3625(3) 0.0228(6) Uani 1 1 d . . . . .
C6 C 0.6924(4) 0.3347(4) 0.3773(3) 0.0286(6) Uani 1 1 d . . . . .
H6A H 0.653028 0.245233 0.396850 0.034 Uiso 1 1 calc R . . . .
C4 C 0.8448(3) 0.5210(4) 0.3182(3) 0.0281(7) Uani 1 1 d . . . . .
H4 H 0.924599 0.584516 0.292373 0.034 Uiso 1 1 calc R . . . .
C5 C 0.8268(4) 0.3864(4) 0.3327(3) 0.0326(7) Uani 1 1 d . . . . .
H5 H 0.889723 0.338443 0.316665 0.039 Uiso 1 1 calc R . . . .
C2 C 0.7774(4) 0.9181(4) 0.3476(4) 0.0307(7) Uani 1 1 d . . . . .
H2A H 0.796740 0.944329 0.447181 0.037 Uiso 1 1 calc R . . . .
H2B H 0.678976 0.920532 0.305466 0.037 Uiso 1 1 calc R . . . .
C12 C 0.3276(4) 0.9121(4) 0.1154(3) 0.0297(7) Uani 1 1 d . . . . .
C3 C 0.7447(4) 0.7117(4) 0.1480(3) 0.0310(7) Uani 1 1 d . . . . .
H3A H 0.740763 0.613346 0.129105 0.037 Uiso 1 1 calc R . . . .
H3B H 0.835118 0.774545 0.126649 0.037 Uiso 1 1 calc R . . . .
C10 C 0.5972(4) 0.7061(4) 0.0541(4) 0.0379(8) Uani 1 1 d . . . . .
H10A H 0.581674 0.655456 -0.039975 0.057 Uiso 1 1 calc GR . . . .
H10B H 0.608189 0.804743 0.060394 0.057 Uiso 1 1 calc GR . . . .
H10C H 0.508626 0.654728 0.082503 0.057 Uiso 1 1 calc GR . . . .
C11 C 0.9091(4) 1.0309(4) 0.3131(4) 0.0403(8) Uani 1 1 d . . . . .
H11A H 0.875659 1.024910 0.216955 0.060 Uiso 1 1 calc GR . . . .
H11B H 0.999775 1.010720 0.331427 0.060 Uiso 1 1 calc GR . . . .
H11C H 0.934815 1.128210 0.369290 0.060 Uiso 1 1 calc GR . . . .
C9 C 0.1230(5) 0.3942(7) 0.1365(4) 0.0640(16) Uani 1 1 d . . . . .
H9 H 0.060047 0.417458 0.072203 0.077 Uiso 1 1 calc R . . . .
C8 C 0.1121(5) 0.2577(7) 0.1351(4) 0.0665(16) Uani 1 1 d . . . . .
H8 H 0.039763 0.169358 0.069416 0.080 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
Ni1 N5 2.099(2) 2_666 ?
Ni1 N5 2.099(2) . ?
Ni1 N1 2.054(2) . ?
Ni1 N1 2.054(2) 2_666 ?
Ni1 N4 2.093(2) 2_666 ?
Ni1 N4 2.093(2) . ?
S1 O1 1.444(2) . ?
S1 O3 1.439(2) . ?
S1 O2 1.445(3) . ?
S1 C12 1.817(3) . ?
F2 C12 1.334(4) . ?
F1 C12 1.327(4) . ?
F3 C12 1.335(4) . ?
N5 C7 1.340(4) . ?
N5 N6 1.350(4) . ?
N3 N4 1.369(3) . ?
N3 C1 1.411(4) . ?
N3 C4 1.375(3) . ?
N1 C1 1.279(4) . ?
N4 C6 1.316(4) . ?
N2 C1 1.358(4) . ?
N2 C2 1.468(4) . ?
N2 C3 1.487(4) . ?
C7 C8 1.374(6) . ?
N6 C9 1.381(6) . ?
C6 C5 1.415(4) . ?
C4 C5 1.362(5) . ?
C2 C11 1.526(4) . ?
C3 C10 1.522(4) . ?
C9 C8 1.355(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 Ni1 N5 180.0 . 2_666 ?
N1 Ni1 N5 90.17(10) 2_666 2_666 ?
N1 Ni1 N5 89.83(10) 2_666 . ?
N1 Ni1 N5 90.17(10) . . ?
N1 Ni1 N5 89.83(10) . 2_666 ?
N1 Ni1 N1 180.0 2_666 . ?
N1 Ni1 N4 101.05(9) 2_666 . ?
N1 Ni1 N4 78.95(9) 2_666 2_666 ?
N1 Ni1 N4 101.05(9) . 2_666 ?
N1 Ni1 N4 78.95(9) . . ?
N4 Ni1 N5 90.87(9) 2_666 2_666 ?
N4 Ni1 N5 90.87(9) . . ?
N4 Ni1 N5 89.13(9) . 2_666 ?
N4 Ni1 N5 89.13(9) 2_666 . ?
N4 Ni1 N4 180.00(16) 2_666 . ?
O1 S1 O2 114.82(15) . . ?
O1 S1 C12 103.48(14) . . ?
O3 S1 O1 114.51(15) . . ?
O3 S1 O2 116.14(16) . . ?
O3 S1 C12 103.25(15) . . ?
O2 S1 C12 102.02(16) . . ?
C7 N5 Ni1 124.5(2) . . ?
C7 N5 N6 107.1(3) . . ?
N6 N5 Ni1 128.4(2) . . ?
N4 N3 C1 118.4(2) . . ?
N4 N3 C4 110.5(2) . . ?
C4 N3 C1 130.6(3) . . ?
C1 N1 Ni1 115.9(2) . . ?
N3 N4 Ni1 109.38(17) . . ?
C6 N4 Ni1 140.1(2) . . ?
C6 N4 N3 106.0(2) . . ?
C1 N2 C2 115.5(2) . . ?
C1 N2 C3 118.4(3) . . ?
C2 N2 C3 117.1(2) . . ?
N5 C7 C8 109.5(4) . . ?
N5 N6 C9 109.3(4) . . ?
N1 C1 N3 115.6(3) . . ?
N1 C1 N2 128.7(3) . . ?
N2 C1 N3 115.6(2) . . ?
N4 C6 C5 110.9(3) . . ?
C5 C4 N3 106.9(3) . . ?
C4 C5 C6 105.7(3) . . ?
N2 C2 C11 111.9(3) . . ?
F2 C12 S1 111.3(2) . . ?
F2 C12 F3 106.9(3) . . ?
F1 C12 S1 112.3(2) . . ?
F1 C12 F2 107.7(2) . . ?
F1 C12 F3 107.4(3) . . ?
F3 C12 S1 110.9(2) . . ?
N2 C3 C10 112.9(3) . . ?
C8 C9 N6 106.7(4) . . ?
C9 C8 C7 107.4(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.521
_oxdiff_exptl_absorpt_empirical_full_min 0.594
####################################################################### 
# 
# 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_737
_database_code_depnum_ccdc_archive 'CCDC 1965150'
_audit_update_record             
;
2019-11-11 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_audit_creation_date             2019-11-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H28 N12 Ni, 2(C F3 O3 S)'
_chemical_formula_sum            'C20 H28 F6 N12 Ni O6 S2'
_chemical_formula_weight         769.37
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Ni1 N4 C10 H20 F3 S1'
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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 '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           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   25.009(2)
_cell_length_b                   9.6962(4)
_cell_length_c                   17.1351(17)
_cell_angle_alpha                90
_cell_angle_beta                 131.427(16)
_cell_angle_gamma                90
_cell_volume                     3115.5(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6120
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      29.7120
_cell_measurement_theta_min      3.2660
_shelx_estimated_absorpt_T_max   0.935
_shelx_estimated_absorpt_T_min   0.905
_exptl_absorpt_coefficient_mu    0.850
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1576
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14306
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         3.171
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -35.00   29.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2518   77.0000   60.0000 64

#__ type_ start__ end____ width___ exp.time_
  2 omega  -39.00   37.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2518   77.0000  150.0000 76

#__ type_ start__ end____ width___ exp.time_
  3 omega    4.00   49.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       21.1893   77.0000    0.0000 45

#__ type_ start__ end____ width___ exp.time_
  4 omega    7.00   66.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       21.1893   77.0000  -90.0000 59

#__ type_ start__ end____ width___ exp.time_
  5 omega  -89.00  -30.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2518  146.0000  166.0000 59

#__ type_ start__ end____ width___ exp.time_
  6 omega   23.00   71.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       21.1893   57.0000   90.0000 48

#__ type_ start__ end____ width___ exp.time_
  7 omega   17.00   75.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       21.1893   57.0000 -180.0000 58

#__ type_ start__ end____ width___ exp.time_
  8 omega   46.00   98.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       21.1893 -178.0000   90.0000 52
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0295285000
_diffrn_orient_matrix_UB_12      -0.0335265000
_diffrn_orient_matrix_UB_13      -0.0110073000
_diffrn_orient_matrix_UB_21      0.0234766000
_diffrn_orient_matrix_UB_22      -0.0472970000
_diffrn_orient_matrix_UB_23      0.0410265000
_diffrn_orient_matrix_UB_31      0.0026695000
_diffrn_orient_matrix_UB_32      0.0445684000
_diffrn_orient_matrix_UB_33      0.0353158000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.998
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                6677
_reflns_number_total             7034
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.606(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         7034
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0310
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0299P)²+0.7591P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0684
_refine_ls_wR_factor_ref         0.0710
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.394(11)
 0.606(11)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 N6(H6), C18(H18), C16(H16), C13(H13), C9(H9), C15(H15), N12(H12), C14(H14),
 C17(H17), C8(H8), C7(H7A), C5(H5), C6(H6A), C4(H4)
3.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C3(H3A,H3B,H3C), C11(H11A,H11B,H11C), C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.84893(2) 0.60849(4) 0.54059(2) 0.01209(10) Uani 1 1 d . . . . .
S1 S 1.03124(4) -0.07433(9) 0.86684(6) 0.01498(17) Uani 1 1 d . . . . .
S2 S 0.64913(5) 1.04084(10) 0.73339(7) 0.0225(2) Uani 1 1 d . . . . .
F2 F 1.01748(13) 0.1117(3) 0.74253(18) 0.0316(6) Uani 1 1 d . . . . .
N7 N 0.75579(17) 0.6046(3) 0.3848(2) 0.0138(6) Uani 1 1 d . . . . .
F1 F 1.09714(12) 0.1606(2) 0.90544(18) 0.0287(5) Uani 1 1 d . . . . .
O2 O 1.09249(15) -0.1227(3) 0.9678(2) 0.0259(6) Uani 1 1 d . . . . .
N9 N 0.87866(15) 0.4944(3) 0.4710(2) 0.0153(6) Uani 1 1 d . . . . .
N8 N 0.71126(15) 0.5514(3) 0.2150(2) 0.0163(6) Uani 1 1 d . . . . .
N1 N 0.94102(16) 0.5626(3) 0.6897(2) 0.0163(6) Uani 1 1 d . . . . .
O1 O 0.97940(14) 0.0011(3) 0.8620(2) 0.0243(6) Uani 1 1 d . . . . .
O3 O 0.99975(14) -0.1722(3) 0.7826(2) 0.0252(6) Uani 1 1 d . . . . .
F3 F 1.11827(12) 0.0044(3) 0.83992(19) 0.0323(6) Uani 1 1 d . . . . .
N4 N 0.82387(15) 0.4244(3) 0.5734(2) 0.0141(6) Uani 1 1 d . . . . .
C20 C 1.0677(2) 0.0582(4) 0.8364(3) 0.0204(8) Uani 1 1 d . . . . .
N3 N 0.88041(15) 0.3696(3) 0.6675(2) 0.0139(6) Uani 1 1 d . . . . .
N6 N 0.84207(16) 0.8951(3) 0.4654(2) 0.0193(7) Uani 1 1 d . . . . .
H6 H 0.7981 0.9002 0.4367 0.023 Uiso 1 1 calc R . . . .
C18 C 0.74101(18) 0.7499(4) 0.5525(3) 0.0182(7) Uani 1 1 d . . . . .
H18 H 0.7010 0.7015 0.4972 0.022 Uiso 1 1 calc R . . . .
O6 O 0.69129(16) 1.0812(4) 0.8407(2) 0.0376(8) Uani 1 1 d . . . . .
C16 C 0.8095(2) 0.8937(4) 0.6824(3) 0.0206(8) Uani 1 1 d . . . . .
H16 H 0.8267 0.9607 0.7330 0.025 Uiso 1 1 calc R . . . .
N11 N 0.80674(15) 0.7316(3) 0.5877(2) 0.0137(6) Uani 1 1 d . . . . .
N10 N 0.82443(15) 0.4814(3) 0.3660(2) 0.0146(6) Uani 1 1 d . . . . .
F5 F 0.71665(13) 0.8041(3) 0.7940(2) 0.0407(7) Uani 1 1 d . . . . .
C13 C 0.8402(2) 0.3838(4) 0.3269(3) 0.0202(8) Uani 1 1 d . . . . .
H13 H 0.8109 0.3551 0.2579 0.024 Uiso 1 1 calc R . . . .
N5 N 0.88484(15) 0.7858(3) 0.5214(2) 0.0145(6) Uani 1 1 d . . . . .
O5 O 0.57475(15) 1.0726(3) 0.6688(2) 0.0364(8) Uani 1 1 d . . . . .
F4 F 0.61152(15) 0.7999(3) 0.6432(2) 0.0450(7) Uani 1 1 d . . . . .
C10 C 0.76025(18) 0.5542(3) 0.3202(3) 0.0139(7) Uani 1 1 d . . . . .
N2 N 0.99137(16) 0.4164(3) 0.8349(2) 0.0189(6) Uani 1 1 d . . . . .
C9 C 0.94766(18) 0.8197(4) 0.5515(3) 0.0194(7) Uani 1 1 d . . . . .
H9 H 0.9880 0.7639 0.5915 0.023 Uiso 1 1 calc R . . . .
C1 C 0.94112(17) 0.4577(4) 0.7351(3) 0.0145(7) Uani 1 1 d . . . . .
C19 C 0.6508(2) 0.8538(4) 0.7386(3) 0.0286(9) Uani 1 1 d . . . . .
C15 C 0.92805(19) 0.4069(4) 0.4959(3) 0.0182(7) Uani 1 1 d . . . . .
H15 H 0.9713 0.3934 0.5630 0.022 Uiso 1 1 calc R . . . .
C12 C 0.7296(2) 0.5904(4) 0.1524(3) 0.0225(8) Uani 1 1 d . . . . .
H12A H 0.7804 0.5879 0.1951 0.034 Uiso 1 1 calc GR . . . .
H12B H 0.7125 0.6819 0.1256 0.034 Uiso 1 1 calc GR . . . .
H12C H 0.7078 0.5269 0.0956 0.034 Uiso 1 1 calc GR . . . .
N12 N 0.84772(16) 0.8218(3) 0.6675(2) 0.0167(6) Uani 1 1 d . . . . .
H12 H 0.8929 0.8316 0.7043 0.020 Uiso 1 1 calc R . . . .
C14 C 0.9066(2) 0.3362(4) 0.4071(3) 0.0202(8) Uani 1 1 d . . . . .
H14 H 0.9325 0.2708 0.4042 0.024 Uiso 1 1 calc R . . . .
C3 C 0.9754(2) 0.3450(4) 0.8932(3) 0.0233(8) Uani 1 1 d . . . . .
H3A H 0.9247 0.3412 0.8517 0.035 Uiso 1 1 calc GR . . . .
H3B H 0.9968 0.3942 0.9565 0.035 Uiso 1 1 calc GR . . . .
H3C H 0.9942 0.2530 0.9095 0.035 Uiso 1 1 calc GR . . . .
O4 O 0.68175(19) 1.0712(3) 0.6905(3) 0.0381(8) Uani 1 1 d . . . . .
C11 C 0.63696(19) 0.5806(4) 0.1633(3) 0.0207(8) Uani 1 1 d . . . . .
H11A H 0.6295 0.6785 0.1567 0.031 Uiso 1 1 calc GR . . . .
H11B H 0.6265 0.5432 0.2039 0.031 Uiso 1 1 calc GR . . . .
H11C H 0.6061 0.5391 0.0955 0.031 Uiso 1 1 calc GR . . . .
C17 C 0.7400(2) 0.8503(4) 0.6091(3) 0.0212(8) Uani 1 1 d . . . . .
H17 H 0.7008 0.8815 0.5996 0.025 Uiso 1 1 calc R . . . .
C8 C 0.9446(2) 0.9510(4) 0.5145(3) 0.0275(9) Uani 1 1 d . . . . .
H8 H 0.9814 0.9980 0.5250 0.033 Uiso 1 1 calc R . . . .
C7 C 0.8769(2) 0.9947(4) 0.4604(3) 0.0243(8) Uani 1 1 d . . . . .
H7A H 0.8580 1.0786 0.4259 0.029 Uiso 1 1 calc R . . . .
F6 F 0.62508(16) 0.8070(3) 0.7807(3) 0.0511(8) Uani 1 1 d . . . . .
C5 C 0.80641(19) 0.1971(4) 0.5761(3) 0.0205(8) Uani 1 1 d . . . . .
H5 H 0.7850 0.1106 0.5549 0.025 Uiso 1 1 calc R . . . .
C6 C 0.77925(18) 0.3207(4) 0.5189(3) 0.0162(7) Uani 1 1 d . . . . .
H6A H 0.7355 0.3285 0.4515 0.019 Uiso 1 1 calc R . . . .
C4 C 0.87126(19) 0.2316(3) 0.6699(3) 0.0180(7) Uani 1 1 d . . . . .
H4 H 0.9031 0.1719 0.7250 0.022 Uiso 1 1 calc R . . . .
C2 C 1.0599(2) 0.4898(4) 0.8991(3) 0.0268(9) Uani 1 1 d . . . . .
H2A H 1.0547 0.5781 0.9189 0.040 Uiso 1 1 calc GR . . . .
H2B H 1.0745 0.5026 0.8600 0.040 Uiso 1 1 calc GR . . . .
H2C H 1.0952 0.4367 0.9604 0.040 Uiso 1 1 calc GR . . . .
H1 H 0.974(3) 0.617(5) 0.731(4) 0.023(12) Uiso 1 1 d . . . . .
H7 H 0.721(3) 0.654(5) 0.358(4) 0.027(12) Uiso 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 N7 2.080(3) . ?
Ni1 N9 2.091(3) . ?
Ni1 N1 2.060(3) . ?
Ni1 N4 2.088(3) . ?
Ni1 N11 2.077(3) . ?
Ni1 N5 2.064(3) . ?
S1 O2 1.432(3) . ?
S1 O1 1.443(3) . ?
S1 O3 1.449(3) . ?
S1 C20 1.839(4) . ?
S2 O6 1.442(3) . ?
S2 O5 1.434(3) . ?
S2 C19 1.815(4) . ?
S2 O4 1.445(3) . ?
F2 C20 1.327(4) . ?
N7 C10 1.280(5) . ?
N7 H7 0.81(5) . ?
F1 C20 1.332(4) . ?
N9 N10 1.365(4) . ?
N9 C15 1.315(5) . ?
N8 C10 1.352(4) . ?
N8 C12 1.467(4) . ?
N8 C11 1.463(4) . ?
N1 C1 1.280(5) . ?
N1 H1 0.83(5) . ?
F3 C20 1.333(4) . ?
N4 N3 1.366(4) . ?
N4 C6 1.323(4) . ?
N3 C1 1.431(4) . ?
N3 C4 1.363(4) . ?
N6 H6 0.8600 . ?
N6 N5 1.353(4) . ?
N6 C7 1.341(5) . ?
C18 H18 0.9300 . ?
C18 N11 1.337(4) . ?
C18 C17 1.386(5) . ?
C16 H16 0.9300 . ?
C16 N12 1.338(5) . ?
C16 C17 1.372(6) . ?
N11 N12 1.353(4) . ?
N10 C13 1.360(5) . ?
N10 C10 1.423(4) . ?
F5 C19 1.333(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.356(5) . ?
N5 C9 1.330(4) . ?
F4 C19 1.336(5) . ?
N2 C1 1.349(4) . ?
N2 C3 1.472(5) . ?
N2 C2 1.469(5) . ?
C9 H9 0.9300 . ?
C9 C8 1.402(5) . ?
C19 F6 1.326(5) . ?
C15 H15 0.9300 . ?
C15 C14 1.412(5) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
N12 H12 0.8600 . ?
C14 H14 0.9300 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C17 H17 0.9300 . ?
C8 H8 0.9300 . ?
C8 C7 1.353(6) . ?
C7 H7A 0.9300 . ?
C5 H5 0.9300 . ?
C5 C6 1.406(5) . ?
C5 C4 1.369(5) . ?
C6 H6A 0.9300 . ?
C4 H4 0.9300 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?

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
N7 Ni1 N9 77.13(12) . . ?
N7 Ni1 N4 92.85(12) . . ?
N1 Ni1 N7 166.34(13) . . ?
N1 Ni1 N9 93.75(12) . . ?
N1 Ni1 N4 76.68(12) . . ?
N1 Ni1 N11 94.64(12) . . ?
N1 Ni1 N5 97.50(12) . . ?
N4 Ni1 N9 89.12(12) . . ?
N11 Ni1 N7 94.80(11) . . ?
N11 Ni1 N9 171.55(11) . . ?
N11 Ni1 N4 93.82(11) . . ?
N5 Ni1 N7 92.63(12) . . ?
N5 Ni1 N9 89.61(11) . . ?
N5 Ni1 N4 173.95(12) . . ?
N5 Ni1 N11 88.26(12) . . ?
O2 S1 O1 115.96(17) . . ?
O2 S1 O3 115.51(17) . . ?
O2 S1 C20 103.68(17) . . ?
O1 S1 O3 113.55(16) . . ?
O1 S1 C20 102.97(17) . . ?
O3 S1 C20 102.70(17) . . ?
O6 S2 C19 103.6(2) . . ?
O6 S2 O4 114.3(2) . . ?
O5 S2 O6 114.0(2) . . ?
O5 S2 C19 103.21(19) . . ?
O5 S2 O4 116.4(2) . . ?
O4 S2 C19 103.04(19) . . ?
Ni1 N7 H7 126(3) . . ?
C10 N7 Ni1 116.9(3) . . ?
C10 N7 H7 114(3) . . ?
N10 N9 Ni1 112.5(2) . . ?
C15 N9 Ni1 140.2(2) . . ?
C15 N9 N10 105.6(3) . . ?
C10 N8 C12 121.6(3) . . ?
C10 N8 C11 118.1(3) . . ?
C11 N8 C12 113.2(3) . . ?
Ni1 N1 H1 126(3) . . ?
C1 N1 Ni1 118.5(3) . . ?
C1 N1 H1 113(3) . . ?
N3 N4 Ni1 112.9(2) . . ?
C6 N4 Ni1 136.3(2) . . ?
C6 N4 N3 105.6(3) . . ?
F2 C20 S1 111.6(3) . . ?
F2 C20 F1 108.0(3) . . ?
F2 C20 F3 108.4(3) . . ?
F1 C20 S1 110.9(2) . . ?
F1 C20 F3 107.5(3) . . ?
F3 C20 S1 110.3(3) . . ?
N4 N3 C1 116.0(3) . . ?
C4 N3 N4 110.8(3) . . ?
C4 N3 C1 132.1(3) . . ?
N5 N6 H6 124.2 . . ?
C7 N6 H6 124.2 . . ?
C7 N6 N5 111.5(3) . . ?
N11 C18 H18 124.3 . . ?
N11 C18 C17 111.4(3) . . ?
C17 C18 H18 124.3 . . ?
N12 C16 H16 126.3 . . ?
N12 C16 C17 107.4(3) . . ?
C17 C16 H16 126.3 . . ?
C18 N11 Ni1 133.7(2) . . ?
C18 N11 N12 104.6(3) . . ?
N12 N11 Ni1 121.6(2) . . ?
N9 N10 C10 117.1(3) . . ?
C13 N10 N9 110.8(3) . . ?
C13 N10 C10 131.5(3) . . ?
N10 C13 H13 126.3 . . ?
C14 C13 N10 107.3(3) . . ?
C14 C13 H13 126.3 . . ?
N6 N5 Ni1 122.8(2) . . ?
C9 N5 Ni1 132.1(3) . . ?
C9 N5 N6 105.0(3) . . ?
N7 C10 N8 129.7(3) . . ?
N7 C10 N10 115.1(3) . . ?
N8 C10 N10 115.0(3) . . ?
C1 N2 C3 123.8(3) . . ?
C1 N2 C2 116.9(3) . . ?
C2 N2 C3 115.2(3) . . ?
N5 C9 H9 124.7 . . ?
N5 C9 C8 110.6(3) . . ?
C8 C9 H9 124.7 . . ?
N1 C1 N3 114.1(3) . . ?
N1 C1 N2 129.2(3) . . ?
N2 C1 N3 116.6(3) . . ?
F5 C19 S2 112.0(3) . . ?
F5 C19 F4 107.0(4) . . ?
F4 C19 S2 110.9(3) . . ?
F6 C19 S2 111.4(3) . . ?
F6 C19 F5 107.7(3) . . ?
F6 C19 F4 107.6(4) . . ?
N9 C15 H15 124.5 . . ?
N9 C15 C14 111.0(3) . . ?
C14 C15 H15 124.5 . . ?
N8 C12 H12A 109.5 . . ?
N8 C12 H12B 109.5 . . ?
N8 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C16 N12 N11 111.8(3) . . ?
C16 N12 H12 124.1 . . ?
N11 N12 H12 124.1 . . ?
C13 C14 C15 105.3(3) . . ?
C13 C14 H14 127.4 . . ?
C15 C14 H14 127.4 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N8 C11 H11A 109.5 . . ?
N8 C11 H11B 109.5 . . ?
N8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C18 C17 H17 127.6 . . ?
C16 C17 C18 104.9(3) . . ?
C16 C17 H17 127.6 . . ?
C9 C8 H8 127.4 . . ?
C7 C8 C9 105.3(3) . . ?
C7 C8 H8 127.4 . . ?
N6 C7 C8 107.6(3) . . ?
N6 C7 H7A 126.2 . . ?
C8 C7 H7A 126.2 . . ?
C6 C5 H5 127.4 . . ?
C4 C5 H5 127.4 . . ?
C4 C5 C6 105.1(3) . . ?
N4 C6 C5 111.3(3) . . ?
N4 C6 H6A 124.4 . . ?
C5 C6 H6A 124.4 . . ?
N3 C4 C5 107.2(3) . . ?
N3 C4 H4 126.4 . . ?
C5 C4 H4 126.4 . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 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
Ni1 N7 C10 N8 -172.4(3) . . . . ?
Ni1 N7 C10 N10 12.7(4) . . . . ?
Ni1 N9 N10 C13 -167.1(2) . . . . ?
Ni1 N9 N10 C10 4.9(3) . . . . ?
Ni1 N9 C15 C14 163.0(3) . . . . ?
Ni1 N1 C1 N3 11.6(4) . . . . ?
Ni1 N1 C1 N2 -171.8(3) . . . . ?
Ni1 N4 N3 C1 12.0(4) . . . . ?
Ni1 N4 N3 C4 -157.5(2) . . . . ?
Ni1 N4 C6 C5 150.6(3) . . . . ?
Ni1 N11 N12 C16 177.9(2) . . . . ?
Ni1 N5 C9 C8 176.8(3) . . . . ?
O2 S1 C20 F2 178.1(3) . . . . ?
O2 S1 C20 F1 -61.5(3) . . . . ?
O2 S1 C20 F3 57.5(3) . . . . ?
N9 N10 C13 C14 -2.1(4) . . . . ?
N9 N10 C10 N7 -11.7(4) . . . . ?
N9 N10 C10 N8 172.6(3) . . . . ?
N9 C15 C14 C13 -1.4(4) . . . . ?
O1 S1 C20 F2 -60.7(3) . . . . ?
O1 S1 C20 F1 59.7(3) . . . . ?
O1 S1 C20 F3 178.7(2) . . . . ?
O3 S1 C20 F2 57.5(3) . . . . ?
O3 S1 C20 F1 177.9(3) . . . . ?
O3 S1 C20 F3 -63.1(3) . . . . ?
N4 N3 C1 N1 -15.6(4) . . . . ?
N4 N3 C1 N2 167.4(3) . . . . ?
N4 N3 C4 C5 -1.6(4) . . . . ?
N3 N4 C6 C5 -0.7(4) . . . . ?
N6 N5 C9 C8 0.0(4) . . . . ?
C18 N11 N12 C16 0.2(4) . . . . ?
O6 S2 C19 F5 -62.6(3) . . . . ?
O6 S2 C19 F4 178.0(3) . . . . ?
O6 S2 C19 F6 58.1(3) . . . . ?
N11 C18 C17 C16 -0.2(4) . . . . ?
N10 N9 C15 C14 0.2(4) . . . . ?
N10 C13 C14 C15 2.1(4) . . . . ?
C13 N10 C10 N7 158.2(4) . . . . ?
C13 N10 C10 N8 -17.4(5) . . . . ?
N5 N6 C7 C8 -0.2(4) . . . . ?
N5 C9 C8 C7 -0.1(5) . . . . ?
O5 S2 C19 F5 178.3(3) . . . . ?
O5 S2 C19 F4 58.8(3) . . . . ?
O5 S2 C19 F6 -61.1(3) . . . . ?
C10 N10 C13 C14 -172.5(3) . . . . ?
C9 C8 C7 N6 0.2(5) . . . . ?
C1 N3 C4 C5 -168.8(4) . . . . ?
C15 N9 N10 C13 1.1(4) . . . . ?
C15 N9 N10 C10 173.1(3) . . . . ?
C12 N8 C10 N7 133.0(4) . . . . ?
C12 N8 C10 N10 -52.2(4) . . . . ?
N12 C16 C17 C18 0.3(4) . . . . ?
C3 N2 C1 N1 147.5(4) . . . . ?
C3 N2 C1 N3 -36.1(5) . . . . ?
O4 S2 C19 F5 56.8(3) . . . . ?
O4 S2 C19 F4 -62.7(3) . . . . ?
O4 S2 C19 F6 177.4(3) . . . . ?
C11 N8 C10 N7 -15.4(6) . . . . ?
C11 N8 C10 N10 159.5(3) . . . . ?
C17 C18 N11 Ni1 -177.3(2) . . . . ?
C17 C18 N11 N12 0.0(4) . . . . ?
C17 C16 N12 N11 -0.3(4) . . . . ?
C7 N6 N5 Ni1 -177.0(2) . . . . ?
C7 N6 N5 C9 0.1(4) . . . . ?
C6 N4 N3 C1 170.9(3) . . . . ?
C6 N4 N3 C4 1.4(4) . . . . ?
C6 C5 C4 N3 1.1(4) . . . . ?
C4 N3 C1 N1 151.0(4) . . . . ?
C4 N3 C1 N2 -25.9(6) . . . . ?
C4 C5 C6 N4 -0.2(4) . . . . ?
C2 N2 C1 N1 -8.6(6) . . . . ?
C2 N2 C1 N3 167.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.394(11)
2 0.606(11)

####################################################################### 
# 
# 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_11255-m-34
_database_code_depnum_ccdc_archive 'CCDC 1966458'
_audit_update_record             
;
2019-11-18 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_audit_creation_date             2019-11-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H32 N12 Ni, 2(C F3 O3 S), 2(C3 H6 O)'
_chemical_formula_sum            'C30 H44 F6 N12 Ni O8 S2'
_chemical_formula_weight         937.60
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H10 N2 Ni1'
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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7256(4)
_cell_length_b                   10.0265(6)
_cell_length_c                   12.2050(7)
_cell_angle_alpha                82.723(5)
_cell_angle_beta                 72.312(5)
_cell_angle_gamma                84.509(4)
_cell_volume                     1007.26(10)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3106
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.3880
_cell_measurement_theta_min      3.2930
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.923
_exptl_absorpt_coefficient_mu    0.676
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92561
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             486
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.876
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10085
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.876
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.972
_diffrn_reflns_theta_min         2.838
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.876
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -43.00   31.00   1.0000    5.2000
omega____ theta____ kappa____ phi______ frames
    -      -22.5803   57.0000   60.0000 74

#__ type_ start__ end____ width___ exp.time_
  2 omega  -79.00   -7.00   1.0000    5.2000
omega____ theta____ kappa____ phi______ frames
    -      -22.5803  123.0000   71.0000 72

#__ type_ start__ end____ width___ exp.time_
  3 omega   35.00   74.00   1.0000    5.2000
omega____ theta____ kappa____ phi______ frames
    -       23.5178 -123.0000   -8.0000 39

#__ type_ start__ end____ width___ exp.time_
  4 omega  -45.00   38.00   1.0000    5.2000
omega____ theta____ kappa____ phi______ frames
    -       23.5178  -57.0000 -180.0000 83

#__ type_ start__ end____ width___ exp.time_
  5 omega   38.00   63.00   1.0000    5.2000
omega____ theta____ kappa____ phi______ frames
    -       23.5178  -99.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega  -21.00   96.00   1.0000    5.2000
omega____ theta____ kappa____ phi______ frames
    -       23.5178   19.0000    0.0000 117

#__ type_ start__ end____ width___ exp.time_
  7 omega   -7.00   18.00   1.0000    5.2000
omega____ theta____ kappa____ phi______ frames
    -       23.5178   77.0000   60.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0108163000
_diffrn_orient_matrix_UB_12      -0.0286184000
_diffrn_orient_matrix_UB_13      -0.0522874000
_diffrn_orient_matrix_UB_21      0.0440816000
_diffrn_orient_matrix_UB_22      0.0555520000
_diffrn_orient_matrix_UB_23      -0.0315460000
_diffrn_orient_matrix_UB_31      0.0724335000
_diffrn_orient_matrix_UB_32      -0.0346378000
_diffrn_orient_matrix_UB_33      0.0056251000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4685
_reflns_number_total             5621
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         5621
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0347
_refine_ls_restrained_S_all      1.028
_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)+(0.0257P)²+0.6030P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0808
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C11(H11A,H11B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N6(H6), C7(H7), C4(H4), C6(H6A), C8(H8), C5(H5), C9(H9)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.500000 0.500000 0.500000 0.01063(7) Uani 1 2 d S T P . .
S1 S 0.54286(4) 0.93922(4) 0.69586(3) 0.01414(9) Uani 1 1 d . . . . .
F3 F 0.49883(15) 1.05305(12) 0.88630(9) 0.0326(3) Uani 1 1 d . . . . .
F1 F 0.41618(14) 0.85182(12) 0.91470(9) 0.0294(3) Uani 1 1 d . . . . .
F2 F 0.27928(13) 1.01724(14) 0.85230(10) 0.0367(3) Uani 1 1 d . . . . .
O2 O 0.44092(14) 0.85702(13) 0.66208(10) 0.0203(3) Uani 1 1 d . . . . .
O1 O 0.55903(15) 1.07343(12) 0.63738(10) 0.0215(3) Uani 1 1 d . . . . .
N1 N 0.63598(14) 0.66532(13) 0.46060(11) 0.0128(3) Uani 1 1 d . . . . .
H1 H 0.593641 0.743740 0.478148 0.015 Uiso 1 1 calc R . . . .
N4 N 0.73030(15) 0.41523(13) 0.44021(11) 0.0127(3) Uani 1 1 d . . . . .
O3 O 0.68955(14) 0.86972(14) 0.70899(12) 0.0282(3) Uani 1 1 d . . . . .
N5 N 0.52167(15) 0.47444(14) 0.67040(12) 0.0137(3) Uani 1 1 d . . . . .
N3 N 0.84517(14) 0.50866(13) 0.40278(11) 0.0121(3) Uani 1 1 d . . . . .
O4 O 1.08384(17) 0.47169(15) 0.10697(12) 0.0296(3) Uani 1 1 d . . . . .
N2 N 0.89379(15) 0.74144(14) 0.36323(12) 0.0137(3) Uani 1 1 d . . . . .
N6 N 0.55678(16) 0.57658(15) 0.71945(12) 0.0168(3) Uani 1 1 d . . . . .
H6 H 0.564251 0.658453 0.688164 0.020 Uiso 1 1 calc R . . . .
C1 C 0.78806(17) 0.64643(16) 0.40825(13) 0.0113(3) Uani 1 1 d . . . . .
C7 C 0.52229(19) 0.36607(17) 0.74557(14) 0.0172(3) Uani 1 1 d . . . . .
H7 H 0.502139 0.280041 0.734688 0.021 Uiso 1 1 calc R . . . .
C4 C 0.99615(18) 0.44521(17) 0.37954(14) 0.0150(3) Uani 1 1 d . . . . .
H4 H 1.093435 0.486717 0.354078 0.018 Uiso 1 1 calc R . . . .
C12 C 0.4289(2) 0.96681(18) 0.84482(14) 0.0188(3) Uani 1 1 d . . . . .
C6 C 0.80944(18) 0.29618(17) 0.43854(14) 0.0151(3) Uani 1 1 d . . . . .
H6A H 0.761121 0.214285 0.459486 0.018 Uiso 1 1 calc R . . . .
C2 C 0.84168(18) 0.88262(16) 0.38416(15) 0.0159(3) Uani 1 1 d . . . . .
H2A H 0.809361 0.893104 0.466126 0.019 Uiso 1 1 calc R . . . .
H2B H 0.752427 0.913476 0.353723 0.019 Uiso 1 1 calc R . . . .
C8 C 0.5573(2) 0.39882(18) 0.84324(15) 0.0203(3) Uani 1 1 d . . . . .
H8 H 0.564516 0.341033 0.907623 0.024 Uiso 1 1 calc R . . . .
C5 C 0.97741(18) 0.31007(17) 0.40064(14) 0.0162(3) Uani 1 1 d . . . . .
H5 H 1.058380 0.241362 0.391898 0.019 Uiso 1 1 calc R . . . .
C9 C 0.57867(19) 0.53459(19) 0.82342(15) 0.0196(3) Uani 1 1 d . . . . .
H9 H 0.603492 0.587497 0.872303 0.023 Uiso 1 1 calc R . . . .
C3 C 1.05479(18) 0.73152(18) 0.27728(15) 0.0181(3) Uani 1 1 d . . . . .
H3A H 1.057727 0.669626 0.221599 0.022 Uiso 1 1 calc R . . . .
H3B H 1.137745 0.702374 0.314470 0.022 Uiso 1 1 calc R . . . .
C14 C 1.0235(2) 0.3718(2) 0.09744(15) 0.0224(4) Uani 1 1 d . . . . .
C11 C 0.9908(2) 0.95951(19) 0.31977(17) 0.0239(4) Uani 1 1 d . . . . .
H11A H 1.058609 0.964217 0.368950 0.029 Uiso 1 1 calc R . . . .
H11B H 0.961462 1.050152 0.291403 0.029 Uiso 1 1 calc R . . . .
C15 C 0.8453(2) 0.3582(2) 0.13858(17) 0.0293(4) Uani 1 1 d . . . . .
H15A H 0.793400 0.433856 0.179380 0.044 Uiso 1 1 calc GR . . . .
H15B H 0.821821 0.276590 0.189353 0.044 Uiso 1 1 calc GR . . . .
H15C H 0.806228 0.355352 0.073420 0.044 Uiso 1 1 calc GR . . . .
C10 C 1.0751(2) 0.87542(19) 0.22012(17) 0.0258(4) Uani 1 1 d . . . . .
H10A H 1.024055 0.892543 0.158929 0.031 Uiso 1 1 calc R . . . .
H10B H 1.188114 0.893860 0.188475 0.031 Uiso 1 1 calc R . . . .
C13 C 1.1265(3) 0.2548(3) 0.0441(2) 0.0464(6) Uani 1 1 d . . . . .
H13A H 1.224088 0.286551 -0.010307 0.070 Uiso 1 1 calc GR . . . .
H13B H 1.069102 0.210259 0.004940 0.070 Uiso 1 1 calc GR . . . .
H13C H 1.152383 0.192756 0.103453 0.070 Uiso 1 1 calc GR . . . .


_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 2.0529(13) . ?
Ni1 N1 2.0529(13) 2_666 ?
Ni1 N4 2.0572(12) 2_666 ?
Ni1 N4 2.0572(12) . ?
Ni1 N5 2.1263(13) . ?
Ni1 N5 2.1264(13) 2_666 ?
S1 O2 1.4455(13) . ?
S1 O1 1.4395(13) . ?
S1 O3 1.4406(12) . ?
S1 C12 1.8295(17) . ?
F3 C12 1.333(2) . ?
F1 C12 1.337(2) . ?
F2 C12 1.3346(19) . ?
N1 H1 0.8600 . ?
N1 C1 1.2932(19) . ?
N4 N3 1.3726(18) . ?
N4 C6 1.320(2) . ?
N5 N6 1.3520(19) . ?
N5 C7 1.331(2) . ?
N3 C1 1.4255(19) . ?
N3 C4 1.3708(18) . ?
O4 C14 1.209(2) . ?
N2 C1 1.337(2) . ?
N2 C2 1.474(2) . ?
N2 C3 1.4792(19) . ?
N6 H6 0.8600 . ?
N6 C9 1.349(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.401(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.363(2) . ?
C6 H6A 0.9300 . ?
C6 C5 1.411(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C11 1.524(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.373(3) . ?
C5 H5 0.9300 . ?
C9 H9 0.9300 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C10 1.523(2) . ?
C14 C15 1.496(2) . ?
C14 C13 1.498(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C10 1.526(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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 N1 180.0 . 2_666 ?
N1 Ni1 N4 77.83(5) 2_666 2_666 ?
N1 Ni1 N4 102.17(5) . 2_666 ?
N1 Ni1 N4 102.17(5) 2_666 . ?
N1 Ni1 N4 77.83(5) . . ?
N1 Ni1 N5 89.67(5) 2_666 . ?
N1 Ni1 N5 90.33(5) . . ?
N1 Ni1 N5 89.67(5) . 2_666 ?
N1 Ni1 N5 90.33(5) 2_666 2_666 ?
N4 Ni1 N4 180.0 . 2_666 ?
N4 Ni1 N5 89.44(5) . . ?
N4 Ni1 N5 90.56(5) . 2_666 ?
N4 Ni1 N5 90.56(5) 2_666 . ?
N4 Ni1 N5 89.44(5) 2_666 2_666 ?
N5 Ni1 N5 180.0 . 2_666 ?
O2 S1 C12 103.32(8) . . ?
O1 S1 O2 115.22(8) . . ?
O1 S1 O3 115.61(8) . . ?
O1 S1 C12 103.43(8) . . ?
O3 S1 O2 114.27(8) . . ?
O3 S1 C12 102.50(8) . . ?
Ni1 N1 H1 121.4 . . ?
C1 N1 Ni1 117.11(11) . . ?
C1 N1 H1 121.4 . . ?
N3 N4 Ni1 113.18(9) . . ?
C6 N4 Ni1 139.95(12) . . ?
C6 N4 N3 106.18(12) . . ?
N6 N5 Ni1 122.15(10) . . ?
C7 N5 Ni1 132.38(12) . . ?
C7 N5 N6 105.14(13) . . ?
N4 N3 C1 116.38(12) . . ?
C4 N3 N4 110.05(13) . . ?
C4 N3 C1 133.10(14) . . ?
C1 N2 C2 118.88(12) . . ?
C1 N2 C3 129.15(14) . . ?
C2 N2 C3 111.24(13) . . ?
N5 N6 H6 124.1 . . ?
C9 N6 N5 111.85(14) . . ?
C9 N6 H6 124.1 . . ?
N1 C1 N3 114.72(14) . . ?
N1 C1 N2 126.75(14) . . ?
N2 C1 N3 118.51(13) . . ?
N5 C7 H7 124.5 . . ?
N5 C7 C8 111.00(16) . . ?
C8 C7 H7 124.5 . . ?
N3 C4 H4 126.3 . . ?
C5 C4 N3 107.37(14) . . ?
C5 C4 H4 126.3 . . ?
F3 C12 S1 111.35(12) . . ?
F3 C12 F1 107.94(14) . . ?
F3 C12 F2 107.45(15) . . ?
F1 C12 S1 111.44(12) . . ?
F2 C12 S1 111.43(11) . . ?
F2 C12 F1 107.00(14) . . ?
N4 C6 H6A 124.6 . . ?
N4 C6 C5 110.77(15) . . ?
C5 C6 H6A 124.6 . . ?
N2 C2 H2A 111.0 . . ?
N2 C2 H2B 111.0 . . ?
N2 C2 C11 103.79(13) . . ?
H2A C2 H2B 109.0 . . ?
C11 C2 H2A 111.0 . . ?
C11 C2 H2B 111.0 . . ?
C7 C8 H8 127.4 . . ?
C9 C8 C7 105.13(15) . . ?
C9 C8 H8 127.4 . . ?
C4 C5 C6 105.63(13) . . ?
C4 C5 H5 127.2 . . ?
C6 C5 H5 127.2 . . ?
N6 C9 C8 106.87(15) . . ?
N6 C9 H9 126.6 . . ?
C8 C9 H9 126.6 . . ?
N2 C3 H3A 111.2 . . ?
N2 C3 H3B 111.2 . . ?
N2 C3 C10 102.63(13) . . ?
H3A C3 H3B 109.2 . . ?
C10 C3 H3A 111.2 . . ?
C10 C3 H3B 111.2 . . ?
O4 C14 C15 122.28(18) . . ?
O4 C14 C13 120.62(18) . . ?
C15 C14 C13 117.10(18) . . ?
C2 C11 H11A 111.2 . . ?
C2 C11 H11B 111.2 . . ?
C2 C11 C10 102.94(14) . . ?
H11A C11 H11B 109.1 . . ?
C10 C11 H11A 111.2 . . ?
C10 C11 H11B 111.2 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C3 C10 C11 102.92(14) . . ?
C3 C10 H10A 111.2 . . ?
C3 C10 H10B 111.2 . . ?
C11 C10 H10A 111.2 . . ?
C11 C10 H10B 111.2 . . ?
H10A C10 H10B 109.1 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

_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_m15
_database_code_depnum_ccdc_archive 'CCDC 1966456'
loop_
_audit_author_name
_audit_author_address
'Avdontceva Margarita'
;St Petersburg State University
Russia
;
_audit_update_record             
;
2020-03-10 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_audit_creation_date             2019-11-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H36 N12 Ni, 2(N O3)'
_chemical_formula_sum            'C22 H36 N14 Ni O6'
_chemical_formula_weight         651.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 N14 No O6'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5039(7)
_cell_length_b                   9.5463(7)
_cell_length_c                   9.7514(8)
_cell_angle_alpha                78.526(6)
_cell_angle_beta                 61.114(8)
_cell_angle_gamma                71.962(7)
_cell_volume                     735.27(11)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4081
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.4480
_cell_measurement_theta_min      4.7970
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.497
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             342
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7422
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        62.477
_diffrn_reflns_theta_max         62.477
_diffrn_reflns_theta_min         4.881
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -75.00 -49.00   0.50    0.20    --  -41.35 127.00  36.00   52
  2  ω    -53.00 -20.00   0.50    0.20    --  -41.35 143.00-153.00   66
  3  ω    -48.00 -13.00   0.50    0.20    --  -41.35 127.00  36.00   70
  4  ω    -92.00 -58.00   0.50    0.20    --  -41.35 143.00-153.00   68
  5  ω     90.00 121.00   0.50    0.55    --  101.00-127.00 -39.00   62
  6  ω     64.00 116.00   0.50    0.55    --  101.00 143.00-153.00  104
  7  ω     97.00 123.00   0.50    0.55    --  101.00-143.00 150.00   52
  8  ω    115.00 140.00   0.50    0.55    --  101.00 127.00  36.00   50
  9  ω    -59.00 -28.00   0.50    0.20    --  -41.35  54.00 -60.00   62
 10  ω   -103.00 -75.00   0.50    0.20    --  -41.35 -43.00-150.00   56
 11  ω    -97.00 -46.00   0.50    0.20    --  -41.35 -54.00 120.00  102
 12  ω    -67.00 -29.00   0.50    0.20    --  -41.35 -43.00-150.00   76
 13  ω   -115.00 -66.00   0.50    0.20    --  -41.35 -11.00-120.00   98
 14  ω    -56.00 -31.00   0.50    0.20    --  -41.35  54.00-120.00   50
 15  ω    -28.00  22.00   0.50    0.20    --  -41.35  54.00-120.00  100
 16  ω    -20.00  18.00   0.50    0.20    --  -41.35  54.00 -60.00   76
 17  ω    -57.00 -22.00   0.50    0.20    --  -41.35 -11.00-120.00   70
 18  ω     56.00  99.00   0.50    0.20    --   41.35-143.00 150.00   86
 19  ω     -2.00  53.00   0.50    0.20    --   41.35 -43.00 -60.00  110
 20  ω     36.00  61.00   0.50    0.20    --   41.35  54.00 150.00   50
 21  ω     -1.00  49.00   0.50    0.20    --   41.35 -32.00 -30.00  100
 22  ω     46.00  71.00   0.50    0.20    --   41.35-127.00 -39.00   50
 23  ω     22.00  47.00   0.50    0.20    --   41.35-143.00 150.00   50
 24  ω     52.00 101.00   0.50    0.20    --   41.35  43.00-180.00   98
 25  ω     30.00  80.00   0.50    0.20    --   41.35  54.00   0.00  100
 26  ω     97.00 155.00   0.50    0.55    --  101.00  93.00  60.00  116
 27  ω     36.00 104.00   0.50    0.55    --  101.00-111.00 150.00  136
 28  ω     41.00 119.00   0.50    0.55    --  101.00 -59.00 -90.00  156
 29  ω     36.00  80.00   0.50    0.55    --  101.00 -25.00 -60.00   88
 30  ω     40.00  95.00   0.50    0.55    --  101.00 -68.00-180.00  110
 31  ω    121.00 152.00   0.50    0.55    --  101.00  93.00 -60.00   62
 32  ω     75.00 157.00   0.50    0.55    --  101.00 133.00-180.00  164
 33  ω     84.00 145.00   0.50    0.55    --  101.00 111.00 -90.00  122
 34  ω     88.00 113.00   0.50    0.55    --  101.00  93.00 -60.00   50
 35  ω     76.00 153.00   0.50    0.55    --  101.00  77.00  90.00  154
 36  ω     50.00 101.00   0.50    0.55    --  101.00 -77.00-120.00  102
 37  ω     82.00 148.00   0.50    0.55    --  101.00 111.00  30.00  132
 38  ω     49.00  75.00   0.50    0.55    --  101.00 -87.00 150.00   52
 39  ω     85.00 110.00   0.50    0.55    --  101.00-111.00-150.00   50
 40  ω    130.00 157.00   0.50    0.55    --  101.00  77.00 -30.00   54
 41  ω     59.00 123.00   0.50    0.55    --  101.00 -87.00 -60.00  128
 42  ω     75.00 106.00   0.50    0.55    --  101.00 -42.00  60.00   62
 43  ω     45.00  97.00   0.50    0.55    --  101.00 -77.00  60.00  104
 44  ω     47.00  80.00   0.50    0.55    --  101.00-111.00-150.00   66
 45  ω    102.00 144.00   0.50    0.55    --  101.00  33.00 150.00   84
 46  ω     49.00  88.00   0.50    0.55    --  101.00-111.00  60.00   78
 47  ω     86.00 136.00   0.50    0.55    --  101.00 133.00 -30.00  100
 48  ω     97.00 133.00   0.50    0.55    --  101.00 111.00-150.00   72
 49  ω     82.00 107.00   0.50    0.55    --  101.00 -87.00 150.00   50
 50  ω    116.00 155.00   0.50    0.55    --  101.00  25.00   0.00   78
 51  ω     80.00 153.00   0.50    0.55    --  101.00 111.00   0.00  146
 52  ω     78.00 109.00   0.50    0.55    --  101.00  77.00 -30.00   62
 53  ω    115.00 141.00   0.50    0.55    --  101.00 143.00-153.00   52
 54  ω    -40.00 -15.00   0.50    0.20    --    8.00 124.00 145.11   50
 55  ω    -34.00  -9.00   0.50    0.20    --   16.00 128.00  -0.59   50
 56  ω     -3.00  22.00   0.50    0.20    --   28.00  94.00 -77.81   50
 57  ω     -4.00  21.00   0.50    0.20    --   28.00  97.00 -24.41   50
 58  ω     -3.00  22.00   0.50    0.20    --   28.00  96.00-161.54   50
 59  ω     -3.00  22.00   0.50    0.20    --   28.00  95.00  71.38   50
 60  ω      4.00  29.00   0.50    0.20    --   32.00  87.00-178.37   50
 61  ω      3.00  28.00   0.50    0.20    --   32.00  89.00-105.93   50
 62  ω      3.00  28.00   0.50    0.20    --   32.00  90.00 111.34   50
 63  ω     17.00  42.00   0.50    0.20    --   40.00  79.00 -23.18   50
 64  ω     15.00  40.00   0.50    0.20    --   40.00  81.00  12.49   50
 65  ω    -76.00 -31.00   0.50    0.20    --  -41.35 138.00 120.00   90
 66  ω    -43.00 -17.00   0.50    0.20    --  -41.35 -77.00 120.00   52
 67  ω     18.00  43.00   0.50    0.20    --   44.00  82.00-110.54   50
 68  ω     19.00  44.00   0.50    0.20    --   44.00  81.00  37.72   50
 69  ω     19.00  44.00   0.50    0.20    --   44.00  78.00 -69.36   50
 70  ω     19.00  44.00   0.50    0.20    --   44.00  79.00  81.28   50
 71  ω     19.00  44.00   0.50    0.20    --   44.00  79.00  57.63   50
 72  ω     30.00  69.00   0.50    0.20    --   48.00  76.00 -47.58   78
 73  ω     26.00  52.00   0.50    0.20    --   48.00  77.00 107.78   52
 74  ω     27.00  53.00   0.50    0.20    --   48.00  75.00 140.26   52
 75  ω     29.00  63.00   0.50    0.20    --   52.00  75.00  -3.81   68
 76  ω     34.00  60.00   0.50    0.20    --   52.00  59.00-102.49   52
 77  ω     74.00 107.00   0.50    0.20    --   52.00  75.00  -3.81   66
 78  ω     32.00  58.00   0.50    0.20    --   56.00  77.00 -94.86   52
 79  ω     82.00 108.00   0.50    0.20    --   56.00  68.00 121.60   52
 80  ω     40.00  66.00   0.50    0.20    --   56.00  68.00 121.60   52
 81  ω     39.00  74.00   0.50    0.20    --   60.00  70.00-170.43   70
 82  ω     39.00  65.00   0.50    0.20    --   64.00  77.00  46.91   52
 83  ω     44.00  70.00   0.50    0.20    --   64.00  63.00  30.18   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0575355000
_diffrn_orient_matrix_UB_12      0.1695361000
_diffrn_orient_matrix_UB_13      -0.0141301000
_diffrn_orient_matrix_UB_21      0.0959877000
_diffrn_orient_matrix_UB_22      -0.0028188000
_diffrn_orient_matrix_UB_23      -0.1801165000
_diffrn_orient_matrix_UB_31      -0.1549566000
_diffrn_orient_matrix_UB_32      -0.0124908000
_diffrn_orient_matrix_UB_33      -0.0054842000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2147
_reflns_number_total             2327
_reflns_odcompleteness_completeness 98.34
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_reflns_special_details          
#the highest value of residual electron density refers to heavy atom# 
;
 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       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.689
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0551
_refine_ls_restrained_S_all      1.056
_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)+(0.0720P)²+1.2976P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1447
_refine_ls_wR_factor_ref         0.1479
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N6(H6), C7(H7), C8(H8), C9(H9), C6(H6A), C5(H5), C4(H4)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.500000 0.500000 0.500000 0.0223(3) Uani 1 2 d S T P . .
O2 O 0.8234(3) 0.6636(3) 0.0744(3) 0.0434(7) Uani 1 1 d . . . . .
N5 N 0.3868(3) 0.6931(3) 0.4057(3) 0.0236(6) Uani 1 1 d . . . . .
N1 N 0.3638(3) 0.5862(3) 0.7194(3) 0.0251(6) Uani 1 1 d . . . . .
H1 H 0.271755 0.566090 0.788650 0.030 Uiso 1 1 calc R . . . .
O1 O 0.9851(3) 0.6928(3) -0.1734(3) 0.0455(7) Uani 1 1 d . . . . .
O3 O 0.7261(3) 0.8122(3) -0.0739(3) 0.0416(7) Uani 1 1 d . . . . .
N4 N 0.6613(3) 0.6075(3) 0.4912(3) 0.0264(6) Uani 1 1 d . . . . .
N6 N 0.4703(3) 0.7549(3) 0.2625(3) 0.0259(6) Uani 1 1 d . . . . .
H6 H 0.574159 0.722233 0.201843 0.031 Uiso 1 1 calc R . . . .
N7 N 0.8462(3) 0.7214(3) -0.0584(3) 0.0305(7) Uani 1 1 d . . . . .
N3 N 0.5977(4) 0.6745(3) 0.6276(3) 0.0336(7) Uani 1 1 d . . . . .
N2 N 0.3649(4) 0.7634(3) 0.8645(4) 0.0392(7) Uani 1 1 d . . . . .
C7 C 0.2303(4) 0.7767(4) 0.4599(4) 0.0260(7) Uani 1 1 d . . . . .
H7 H 0.143394 0.760356 0.556697 0.031 Uiso 1 1 calc R . . . .
C8 C 0.2168(4) 0.8921(4) 0.3496(4) 0.0273(7) Uani 1 1 d . . . . .
H8 H 0.122428 0.965691 0.358379 0.033 Uiso 1 1 calc R . . . .
C9 C 0.3717(4) 0.8731(4) 0.2268(4) 0.0296(7) Uani 1 1 d . . . . .
H9 H 0.403205 0.932295 0.134217 0.036 Uiso 1 1 calc R . . . .
C6 C 0.8187(4) 0.6085(4) 0.4095(4) 0.0316(8) Uani 1 1 d . . . . .
H6A H 0.890634 0.571386 0.311164 0.038 Uiso 1 1 calc R . . . .
C5 C 0.8601(5) 0.6775(5) 0.4995(5) 0.0446(10) Uani 1 1 d . . . . .
H5 H 0.962818 0.693411 0.470823 0.054 Uiso 1 1 calc R . . . .
C1 C 0.4305(5) 0.6734(4) 0.7422(4) 0.0344(8) Uani 1 1 d . . . . .
C4 C 0.7197(5) 0.7144(4) 0.6337(5) 0.0413(9) Uani 1 1 d . . . . .
H4 H 0.708512 0.759249 0.715948 0.050 Uiso 1 1 calc R . . . .
C2 C 0.2205(5) 0.7276(5) 1.0075(5) 0.0472(10) Uani 1 1 d . . . . .
H2A H 0.140036 0.717538 0.978373 0.057 Uiso 1 1 calc R . . . .
H2B H 0.168043 0.808045 1.076956 0.057 Uiso 1 1 calc R . . . .
C11 C 0.2717(5) 0.5842(5) 1.0945(5) 0.0433(9) Uani 1 1 d . . . . .
H11A H 0.320920 0.503907 1.027008 0.065 Uiso 1 1 calc GR . . . .
H11B H 0.175640 0.564958 1.186759 0.065 Uiso 1 1 calc GR . . . .
H11C H 0.350711 0.594165 1.124264 0.065 Uiso 1 1 calc GR . . . .
C3 C 0.3538(7) 0.9209(5) 0.8219(6) 0.0565(12) Uani 1 1 d . . . . .
H3A H 0.461958 0.933511 0.742654 0.068 Uiso 1 1 calc R . . . .
H3B H 0.323970 0.970318 0.913485 0.068 Uiso 1 1 calc R . . . .
C10 C 0.2287(9) 0.9932(5) 0.7601(8) 0.087(2) Uani 1 1 d . . . . .
H10A H 0.265143 0.953968 0.661811 0.130 Uiso 1 1 calc GR . . . .
H10B H 0.218139 1.097795 0.745097 0.130 Uiso 1 1 calc GR . . . .
H10C H 0.123225 0.974072 0.834114 0.130 Uiso 1 1 calc GR . . . .


_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 N5 2.110(2) . ?
Ni1 N5 2.110(2) 2_666 ?
Ni1 N1 2.072(3) . ?
Ni1 N1 2.072(3) 2_666 ?
Ni1 N4 2.054(3) . ?
Ni1 N4 2.054(3) 2_666 ?
O2 N7 1.244(4) . ?
N5 N6 1.349(4) . ?
N5 C7 1.342(4) . ?
N1 C1 1.297(5) . ?
O1 N7 1.242(4) . ?
O3 N7 1.257(4) . ?
N4 N3 1.365(4) . ?
N4 C6 1.314(4) . ?
N6 C9 1.333(4) . ?
N3 C1 1.437(5) . ?
N3 C4 1.357(5) . ?
N2 C1 1.381(5) . ?
N2 C2 1.482(5) . ?
N2 C3 1.463(5) . ?
C7 C8 1.400(5) . ?
C8 C9 1.361(5) . ?
C6 C5 1.443(5) . ?
C5 C4 1.350(6) . ?
C2 C11 1.535(6) . ?
C3 C10 1.507(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
N5 Ni1 N5 180.0 2_666 . ?
N1 Ni1 N5 90.35(10) 2_666 . ?
N1 Ni1 N5 89.65(10) . . ?
N1 Ni1 N5 89.65(10) 2_666 2_666 ?
N1 Ni1 N5 90.35(10) . 2_666 ?
N1 Ni1 N1 180.0 2_666 . ?
N4 Ni1 N5 90.04(10) . . ?
N4 Ni1 N5 90.04(10) 2_666 2_666 ?
N4 Ni1 N5 89.96(10) 2_666 . ?
N4 Ni1 N5 89.96(10) . 2_666 ?
N4 Ni1 N1 80.32(10) . . ?
N4 Ni1 N1 99.68(10) 2_666 . ?
N4 Ni1 N1 99.68(10) . 2_666 ?
N4 Ni1 N1 80.32(10) 2_666 2_666 ?
N4 Ni1 N4 180.0 . 2_666 ?
N6 N5 Ni1 122.44(19) . . ?
C7 N5 Ni1 132.2(2) . . ?
C7 N5 N6 105.3(2) . . ?
C1 N1 Ni1 113.6(2) . . ?
N3 N4 Ni1 110.8(2) . . ?
C6 N4 Ni1 139.0(2) . . ?
C6 N4 N3 108.4(3) . . ?
C9 N6 N5 111.5(3) . . ?
O2 N7 O3 118.6(3) . . ?
O1 N7 O2 121.1(3) . . ?
O1 N7 O3 120.3(3) . . ?
N4 N3 C1 118.0(3) . . ?
C4 N3 N4 109.4(3) . . ?
C4 N3 C1 132.0(3) . . ?
C1 N2 C2 115.2(3) . . ?
C1 N2 C3 116.2(3) . . ?
C3 N2 C2 115.3(3) . . ?
N5 C7 C8 110.1(3) . . ?
C9 C8 C7 105.0(3) . . ?
N6 C9 C8 108.1(3) . . ?
N4 C6 C5 107.9(3) . . ?
C4 C5 C6 106.1(3) . . ?
N1 C1 N3 116.2(3) . . ?
N1 C1 N2 129.0(3) . . ?
N2 C1 N3 114.8(3) . . ?
C5 C4 N3 108.1(3) . . ?
N2 C2 C11 111.7(3) . . ?
N2 C3 C10 113.3(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.697
_oxdiff_exptl_absorpt_empirical_full_min 0.483
####################################################################### 
# 
# 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_0ver0-9022_m17
_database_code_depnum_ccdc_archive 'CCDC 1966459'
loop_
_audit_author_name
_audit_author_address
'Avdontceva Margarita'
;St Petersburg State University
Russia
;
_audit_update_record             
;
2020-03-10 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_audit_creation_date             2019-11-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H36 N12 Ni, 2(N O3)'
_chemical_formula_sum            'C24 H36 N14 Ni O6'
_chemical_formula_weight         675.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C24 N14 Ni O6'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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 1 21/n 1'
_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                   8.3309(4)
_cell_length_b                   9.7597(4)
_cell_length_c                   18.0944(11)
_cell_angle_alpha                90
_cell_angle_beta                 98.938(5)
_cell_angle_gamma                90
_cell_volume                     1453.34(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2105
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.0160
_cell_measurement_theta_min      4.9440
_shelx_estimated_absorpt_T_max   0.913
_shelx_estimated_absorpt_T_min   0.861
_exptl_absorpt_coefficient_mu    1.540
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62332
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5574
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.487
_diffrn_reflns_theta_max         67.487
_diffrn_reflns_theta_min         4.948
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -67.00  35.00   1.00   15.00    --  -40.38  38.00-120.00  102
  2  ω    -67.00  26.00   1.00   15.00    --  -40.38  38.00 150.00   93
  3  ω     90.00 129.00   1.00   15.00    --   40.38 178.00 -60.00   39
  4  ω     96.00 125.00   1.00   15.00    --   40.38 178.00-150.00   29
  5  ω     85.00 115.00   1.00   45.00    --  113.00-112.00-120.00   30
  6  ω    103.00 167.00   1.00   45.00    --  113.00 112.00   0.00   64
  7  ω     86.00 172.00   1.00   45.00    --  113.00  45.00-180.00   86
  8  ω     50.00 106.00   1.00   45.00    --  113.00 -95.00   0.00   56
  9  ω     42.00  97.00   1.00   45.00    --  113.00 -95.00 -30.00   55
 10  ω    107.00 148.00   1.00   45.00    --  113.00 112.00 -90.00   41
 11  ω     41.00 139.00   1.00   45.00    --  113.00 -45.00   0.00   98
 12  ω     81.00 140.00   1.00   45.00    --  113.00 178.00 -60.00   59
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1067778000
_diffrn_orient_matrix_UB_12      0.1264212000
_diffrn_orient_matrix_UB_13      0.0231202000
_diffrn_orient_matrix_UB_21      0.1369846000
_diffrn_orient_matrix_UB_22      -0.0940812000
_diffrn_orient_matrix_UB_23      0.0379192000
_diffrn_orient_matrix_UB_31      0.0697851000
_diffrn_orient_matrix_UB_32      -0.0085621000
_diffrn_orient_matrix_UB_33      -0.0738896000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2186
_reflns_number_total             2612
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_reflns_special_details          
#the highest value of residual electron density refers to heavy atom# 
;
 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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.756
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2612
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0700
_refine_ls_restrained_S_all      1.075
_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)+(0.0786P)²+3.0428P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1762
_refine_ls_wR_factor_ref         0.1860
_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
2. Uiso/Uaniso restraints and constraints
Uanis(C10) = Uanis(C10')
3. Others
 Fixed Sof: C10(0.7) H10A(0.7) H10B(0.7) C2'(0.6) H2'A(0.6) H2'B(0.6) C3'(0.6)
 H3'A(0.6) H3'B(0.6) C12(0.6) H12A(0.6) H12B(0.6) C3(0.4) H3A(0.4) H3B(0.4)
 C2(0.4) H2A(0.4) H2B(0.4) C12'(0.4) H12C(0.4) H12D(0.4) C10'(0.3) H10C(0.3)
 H10D(0.3)
4.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C2'(H2'A,H2'B), C3'(H3'A,H3'B), C12(H12A,H12B), C3(H3A,H3B),
 C2(H2A,H2B), C12'(H12C,H12D), C10'(H10C,H10D)
4.b Aromatic/amide H refined with riding coordinates:
 N6(H6), N1(H1), C8(H8), C7(H7), C9(H9), C6(H6A), C5(H5), C4(H4), C11(H11A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.500000 0.500000 0.500000 0.0346(3) Uani 1 2 d S T P . .
O3 O 0.3580(5) 1.1135(3) 0.4072(2) 0.0602(10) Uani 1 1 d . . . . .
N5 N 0.3550(4) 0.5245(3) 0.3948(2) 0.0365(8) Uani 1 1 d . . . . .
N4 N 0.3058(4) 0.4105(4) 0.5423(2) 0.0395(8) Uani 1 1 d . . . . .
N6 N 0.3057(4) 0.6472(4) 0.3668(2) 0.0413(8) Uani 1 1 d . . . . .
H6 H 0.329249 0.725482 0.390189 0.050 Uiso 1 1 calc R . . . .
N7 N 0.3357(5) 0.9876(4) 0.4128(2) 0.0448(9) Uani 1 1 d . . . . .
N1 N 0.3947(4) 0.6700(3) 0.5400(2) 0.0396(8) Uani 1 1 d . . . . .
H1 H 0.430292 0.753404 0.533682 0.048 Uiso 1 1 calc R . . . .
N3 N 0.2116(4) 0.5085(4) 0.5712(2) 0.0453(9) Uani 1 1 d . . . . .
O2 O 0.4465(5) 0.9058(4) 0.4125(3) 0.0708(12) Uani 1 1 d . . . . .
O1 O 0.2000(5) 0.9441(5) 0.4168(3) 0.0929(16) Uani 1 1 d . . . . .
N2 N 0.1934(6) 0.7371(5) 0.6140(3) 0.0642(13) Uani 1 1 d . . . . .
C8 C 0.2055(6) 0.5003(5) 0.2812(3) 0.0464(10) Uani 1 1 d . . . . .
H8 H 0.149761 0.459907 0.236695 0.056 Uiso 1 1 calc R . . . .
C7 C 0.2945(5) 0.4346(5) 0.3427(3) 0.0445(10) Uani 1 1 d . . . . .
H7 H 0.309935 0.338327 0.346804 0.053 Uiso 1 1 calc R . . . .
C9 C 0.2167(5) 0.6362(5) 0.2995(3) 0.0463(11) Uani 1 1 d . . . . .
H9 H 0.169184 0.709808 0.269360 0.056 Uiso 1 1 calc R . . . .
C6 C 0.2223(5) 0.2972(5) 0.5371(3) 0.0494(12) Uani 1 1 d . . . . .
H6A H 0.256088 0.212977 0.518142 0.059 Uiso 1 1 calc R . . . .
C5 C 0.0745(6) 0.3187(5) 0.5637(3) 0.0550(13) Uani 1 1 d . . . . .
H5 H -0.005203 0.251226 0.568771 0.066 Uiso 1 1 calc R . . . .
C1 C 0.2711(6) 0.6464(5) 0.5754(3) 0.0467(11) Uani 1 1 d . . . . .
C4 C 0.0670(7) 0.4529(6) 0.5807(3) 0.0626(14) Uani 1 1 d . . . . .
H4 H -0.022226 0.499443 0.596183 0.075 Uiso 1 1 calc R . . . .
C11 C 0.1357(10) 0.9383(7) 0.7235(4) 0.0780(18) Uani 1 1 d . . . . .
H11A H 0.173901 0.986281 0.768470 0.094 Uiso 1 1 calc R . . A 2
H11 H 0.037(9) 0.986(7) 0.708(4) 0.094 Uiso 1 1 d R . . B 1
C10 C 0.1290(13) 0.7912(10) 0.7380(5) 0.068(2) Uani 0.7 1 d . . . C 1
H10A H 0.052015 0.774209 0.773512 0.081 Uiso 0.7 1 calc R . . C 1
H10B H 0.237668 0.759418 0.761719 0.081 Uiso 0.7 1 calc R . . C 1
C2' C 0.1885(13) 0.8881(11) 0.5949(6) 0.054(2) Uani 0.6 1 d . . . C 1
H2'A H 0.255053 0.905985 0.555137 0.064 Uiso 0.6 1 calc R . . C 1
H2'B H 0.075319 0.916357 0.576224 0.064 Uiso 0.6 1 calc R . . C 1
C3' C 0.0765(12) 0.7099(10) 0.6679(6) 0.062(2) Uani 0.6 1 d . . . C 1
H3'A H -0.034699 0.737025 0.645057 0.075 Uiso 0.6 1 calc R . . C 1
H3'B H 0.075731 0.610945 0.679843 0.075 Uiso 0.6 1 calc R . . C 1
C12 C 0.2521(16) 0.9667(10) 0.6622(6) 0.063(2) Uani 0.6 1 d . . . C 1
H12A H 0.253205 1.065695 0.650313 0.076 Uiso 0.6 1 calc R . . C 1
H12B H 0.364601 0.937610 0.681613 0.076 Uiso 0.6 1 calc R . . C 1
C3 C 0.200(2) 0.700(2) 0.6982(9) 0.081(5) Uani 0.4 1 d . . . C 2
H3A H 0.305205 0.723310 0.728943 0.097 Uiso 0.4 1 calc R . . C 2
H3B H 0.172189 0.602833 0.705991 0.097 Uiso 0.4 1 calc R . . C 2
C2 C 0.276(2) 0.8762(18) 0.6189(12) 0.067(5) Uani 0.4 1 d . . . C 2
H2A H 0.303371 0.904185 0.569765 0.081 Uiso 0.4 1 calc R . . C 2
H2B H 0.376578 0.875295 0.656184 0.081 Uiso 0.4 1 calc R . . C 2
C12' C 0.146(3) 0.973(2) 0.6439(13) 0.090(6) Uani 0.4 1 d . . . C 2
H12C H 0.178526 1.070162 0.639777 0.108 Uiso 0.4 1 calc R . . C 2
H12D H 0.039456 0.959219 0.612081 0.108 Uiso 0.4 1 calc R . . C 2
C10' C 0.049(3) 0.809(3) 0.7113(13) 0.068(2) Uani 0.3 1 d . . . C 2
H10C H -0.035683 0.812835 0.666595 0.081 Uiso 0.3 1 calc R . . C 2
H10D H -0.000666 0.782400 0.755330 0.081 Uiso 0.3 1 calc R . . C 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 N5 2.103(4) . ?
Ni1 N5 2.103(4) 3_666 ?
Ni1 N4 2.086(3) . ?
Ni1 N4 2.087(3) 3_666 ?
Ni1 N1 2.059(3) 3_666 ?
Ni1 N1 2.059(3) . ?
O3 N7 1.249(5) . ?
N5 N6 1.340(5) . ?
N5 C7 1.328(6) . ?
N4 N3 1.390(5) . ?
N4 C6 1.301(5) . ?
N6 C9 1.329(6) . ?
N7 O2 1.221(5) . ?
N7 O1 1.220(5) . ?
N1 C1 1.315(6) . ?
N3 C1 1.433(6) . ?
N3 C4 1.356(6) . ?
N2 C1 1.354(6) . ?
N2 C2' 1.513(11) . ?
N2 C3' 1.504(9) . ?
N2 C3 1.559(17) . ?
N2 C2 1.519(17) . ?
C8 C7 1.395(7) . ?
C8 C9 1.366(7) . ?
C6 C5 1.406(6) . ?
C5 C4 1.349(7) . ?
C11 C10 1.462(12) . ?
C11 C12 1.607(12) . ?
C11 C12' 1.49(2) . ?
C11 C10' 1.45(3) . ?
C10 C3' 1.503(14) . ?
C2' C12 1.467(15) . ?
C3 C10' 1.69(3) . ?
C2 C12' 1.56(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 Ni1 N5 180.0 3_666 . ?
N4 Ni1 N5 90.60(14) . . ?
N4 Ni1 N5 89.40(14) . 3_666 ?
N4 Ni1 N5 90.60(14) 3_666 3_666 ?
N4 Ni1 N5 89.40(14) 3_666 . ?
N4 Ni1 N4 180.0 . 3_666 ?
N1 Ni1 N5 90.58(14) 3_666 3_666 ?
N1 Ni1 N5 89.42(14) 3_666 . ?
N1 Ni1 N5 89.42(14) . 3_666 ?
N1 Ni1 N5 90.58(14) . . ?
N1 Ni1 N4 100.86(13) 3_666 . ?
N1 Ni1 N4 79.14(13) 3_666 3_666 ?
N1 Ni1 N4 79.14(13) . . ?
N1 Ni1 N4 100.86(13) . 3_666 ?
N1 Ni1 N1 180.0 . 3_666 ?
N6 N5 Ni1 122.9(3) . . ?
C7 N5 Ni1 132.0(3) . . ?
C7 N5 N6 105.2(4) . . ?
N3 N4 Ni1 111.4(2) . . ?
C6 N4 Ni1 139.9(3) . . ?
C6 N4 N3 106.6(3) . . ?
C9 N6 N5 111.6(4) . . ?
O2 N7 O3 121.4(4) . . ?
O1 N7 O3 119.8(4) . . ?
O1 N7 O2 118.7(4) . . ?
C1 N1 Ni1 116.0(3) . . ?
N4 N3 C1 117.1(3) . . ?
C4 N3 N4 109.7(4) . . ?
C4 N3 C1 132.5(4) . . ?
C1 N2 C2' 121.1(5) . . ?
C1 N2 C3' 129.0(5) . . ?
C1 N2 C3 113.9(8) . . ?
C1 N2 C2 111.4(7) . . ?
C3' N2 C2' 108.8(6) . . ?
C2 N2 C3 101.8(11) . . ?
C9 C8 C7 104.2(4) . . ?
N5 C7 C8 111.1(4) . . ?
N6 C9 C8 108.0(4) . . ?
N4 C6 C5 109.6(4) . . ?
C4 C5 C6 107.3(4) . . ?
N1 C1 N3 115.4(4) . . ?
N1 C1 N2 127.7(4) . . ?
N2 C1 N3 116.9(4) . . ?
C5 C4 N3 106.6(4) . . ?
C10 C11 C12 109.7(6) . . ?
C10' C11 C12' 98.8(12) . . ?
C11 C10 C3' 112.4(8) . . ?
C12 C2' N2 109.1(8) . . ?
C10 C3' N2 108.7(7) . . ?
C2' C12 C11 107.7(9) . . ?
N2 C3 C10' 94.4(14) . . ?
N2 C2 C12' 103.3(13) . . ?
C11 C12' C2 106.7(17) . . ?
C11 C10' C3 102.1(16) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.846
_oxdiff_exptl_absorpt_empirical_full_min 0.262
####################################################################### 
# 
# 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_08310-8516_m11
_database_code_depnum_ccdc_archive 'CCDC 1966454'
_audit_update_record             
;
2019-11-18 deposited with the CCDC.	2020-04-06 downloaded from the CCDC.
;
_audit_creation_date             2019-11-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H28 N12 Ni, 2(Cl)'
_chemical_formula_sum            'C18 H28 Cl2 N12 Ni'
_chemical_formula_weight         542.13
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 Cl2 Cu N12'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   19.9358(11)
_cell_length_b                   9.2467(3)
_cell_length_c                   16.9617(10)
_cell_angle_alpha                90
_cell_angle_beta                 126.983(8)
_cell_angle_gamma                90
_cell_volume                     2497.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4877
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.7020
_cell_measurement_theta_min      3.0350
_shelx_estimated_absorpt_T_max   0.951
_shelx_estimated_absorpt_T_min   0.896
_exptl_absorpt_coefficient_mu    1.023
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94027
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9275
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.547
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -14.00   19.00   1.0000   11.9700
omega____ theta____ kappa____ phi______ frames
    -      -22.2678  -99.0000  150.0000 33

#__ type_ start__ end____ width___ exp.time_
  2 omega  -89.00  -14.00   1.0000   11.9700
omega____ theta____ kappa____ phi______ frames
    -      -22.2678  -57.0000   30.0000 75

#__ type_ start__ end____ width___ exp.time_
  3 omega  -89.00  -43.00   1.0000   11.9700
omega____ theta____ kappa____ phi______ frames
    -      -22.2678 -178.0000  150.0000 46

#__ type_ start__ end____ width___ exp.time_
  4 omega  -24.00    2.00   1.0000   11.9700
omega____ theta____ kappa____ phi______ frames
    -      -22.2678  -99.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   55.00   88.00   1.0000   11.9700
omega____ theta____ kappa____ phi______ frames
    -       23.3616   57.0000 -180.0000 33

#__ type_ start__ end____ width___ exp.time_
  6 omega   41.00   98.00   1.0000   11.9700
omega____ theta____ kappa____ phi______ frames
    -       23.3616 -178.0000   60.0000 57

#__ type_ start__ end____ width___ exp.time_
  7 omega   22.00   48.00   1.0000   11.9700
omega____ theta____ kappa____ phi______ frames
    -      -22.2678   38.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega  -62.00  -37.00   1.0000   11.9700
omega____ theta____ kappa____ phi______ frames
    -      -22.2678 -178.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
  9 omega  -90.00  -48.00   1.0000   11.9700
omega____ theta____ kappa____ phi______ frames
    -      -22.2678  -57.0000 -120.0000 42

#__ type_ start__ end____ width___ exp.time_
 10 omega  -90.00  -65.00   1.0000   11.9700
omega____ theta____ kappa____ phi______ frames
    -      -22.2678  -77.0000  -60.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0202453000
_diffrn_orient_matrix_UB_12      -0.0055236000
_diffrn_orient_matrix_UB_13      -0.0228046000
_diffrn_orient_matrix_UB_21      0.0242035000
_diffrn_orient_matrix_UB_22      -0.0588531000
_diffrn_orient_matrix_UB_23      0.0313335000
_diffrn_orient_matrix_UB_31      -0.0314565000
_diffrn_orient_matrix_UB_32      -0.0488456000
_diffrn_orient_matrix_UB_33      -0.0352275000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2605
_reflns_number_total             2868
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         2868
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0302
_refine_ls_restrained_S_all      1.057
_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)+(0.0264P)²+3.2709P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0688
_refine_ls_wR_factor_ref         0.0715
_refine_special_details          ?
_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 C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N6(H6), C7(H7), C4(H4), C5(H5), C8(H8), C6(H6A), C9(H9)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.500000 0.67671(3) 0.250000 0.01001(9) Uani 1 2 d S T P . .
Cl1 Cl 0.34640(3) 0.64163(5) 0.36021(3) 0.02010(11) Uani 1 1 d . . . . .
N1 N 0.51847(8) 0.70471(15) 0.38252(10) 0.0129(3) Uani 1 1 d . . . . .
H1 H 0.488669 0.658767 0.395516 0.015 Uiso 1 1 calc R . . . .
N3 N 0.62630(8) 0.85015(15) 0.41827(10) 0.0124(3) Uani 1 1 d . . . . .
N2 N 0.59696(9) 0.83279(16) 0.53361(10) 0.0165(3) Uani 1 1 d . . . . .
N6 N 0.36141(8) 0.46610(16) 0.21431(10) 0.0153(3) Uani 1 1 d . . . . .
H6 H 0.355352 0.512514 0.253601 0.018 Uiso 1 1 calc R . . . .
N5 N 0.41065(8) 0.51072(15) 0.18872(10) 0.0133(3) Uani 1 1 d . . . . .
N4 N 0.59734(9) 0.82881(15) 0.32288(10) 0.0132(3) Uani 1 1 d . . . . .
C7 C 0.40222(10) 0.40955(19) 0.12733(13) 0.0175(4) Uani 1 1 d . . . . .
H7 H 0.428912 0.411615 0.097447 0.021 Uiso 1 1 calc R . . . .
C4 C 0.70568(10) 0.90643(19) 0.47289(12) 0.0155(3) Uani 1 1 d . . . . .
H4 H 0.738979 0.927229 0.540023 0.019 Uiso 1 1 calc R . . . .
C5 C 0.72706(10) 0.92642(19) 0.41124(13) 0.0172(4) Uani 1 1 d . . . . .
H5 H 0.776646 0.965629 0.426763 0.021 Uiso 1 1 calc R . . . .
C8 C 0.34814(11) 0.3004(2) 0.11392(13) 0.0218(4) Uani 1 1 d . . . . .
H8 H 0.332337 0.218114 0.074909 0.026 Uiso 1 1 calc R . . . .
C1 C 0.57605(10) 0.79322(18) 0.44472(12) 0.0127(3) Uani 1 1 d . . . . .
C6 C 0.65794(10) 0.87498(18) 0.31870(13) 0.0156(3) Uani 1 1 d . . . . .
H6A H 0.655285 0.873661 0.262053 0.019 Uiso 1 1 calc R . . . .
C9 C 0.32314(11) 0.3400(2) 0.17052(13) 0.0203(4) Uani 1 1 d . . . . .
H9 H 0.286624 0.289323 0.177356 0.024 Uiso 1 1 calc R . . . .
C2 C 0.56188(12) 0.7467(2) 0.57337(13) 0.0220(4) Uani 1 1 d . . . . .
H2A H 0.502969 0.766763 0.536660 0.033 Uiso 1 1 calc GR . . . .
H2B H 0.589854 0.771236 0.641473 0.033 Uiso 1 1 calc GR . . . .
H2C H 0.569836 0.645801 0.568048 0.033 Uiso 1 1 calc GR . . . .
C3 C 0.62397(11) 0.9789(2) 0.57505(14) 0.0214(4) Uani 1 1 d . . . . .
H3A H 0.630506 1.036837 0.533120 0.032 Uiso 1 1 calc GR . . . .
H3B H 0.676589 0.973472 0.639711 0.032 Uiso 1 1 calc GR . . . .
H3C H 0.582477 1.021858 0.579425 0.032 Uiso 1 1 calc GR . . . .


_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 2.0638(14) . ?
Ni1 N1 2.0638(14) 2_655 ?
Ni1 N5 2.0932(14) . ?
Ni1 N5 2.0932(14) 2_655 ?
Ni1 N4 2.0942(14) 2_655 ?
Ni1 N4 2.0942(14) . ?
N1 C1 1.282(2) . ?
N3 N4 1.3661(19) . ?
N3 C4 1.367(2) . ?
N3 C1 1.422(2) . ?
N2 C1 1.351(2) . ?
N2 C2 1.464(2) . ?
N2 C3 1.467(2) . ?
N6 N5 1.3547(19) . ?
N6 C9 1.346(2) . ?
N5 C7 1.333(2) . ?
N4 C6 1.323(2) . ?
C7 C8 1.392(3) . ?
C4 C5 1.358(2) . ?
C5 C6 1.409(2) . ?
C8 C9 1.371(3) . ?

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 N1 165.58(8) . 2_655 ?
N1 Ni1 N5 100.01(5) . . ?
N1 Ni1 N5 90.58(5) . 2_655 ?
N1 Ni1 N5 90.59(5) 2_655 . ?
N1 Ni1 N5 100.01(5) 2_655 2_655 ?
N1 Ni1 N4 93.07(5) 2_655 . ?
N1 Ni1 N4 77.18(5) 2_655 2_655 ?
N1 Ni1 N4 93.06(5) . 2_655 ?
N1 Ni1 N4 77.17(5) . . ?
N5 Ni1 N5 85.67(7) 2_655 . ?
N5 Ni1 N4 174.33(5) 2_655 2_655 ?
N5 Ni1 N4 174.33(5) . . ?
N5 Ni1 N4 89.42(5) . 2_655 ?
N5 Ni1 N4 89.42(5) 2_655 . ?
N4 Ni1 N4 95.62(8) . 2_655 ?
C1 N1 Ni1 117.46(11) . . ?
N4 N3 C4 110.47(14) . . ?
N4 N3 C1 116.37(13) . . ?
C4 N3 C1 132.45(14) . . ?
C1 N2 C2 117.04(14) . . ?
C1 N2 C3 124.19(15) . . ?
C2 N2 C3 114.76(14) . . ?
C9 N6 N5 111.49(15) . . ?
N6 N5 Ni1 128.94(11) . . ?
C7 N5 Ni1 124.90(12) . . ?
C7 N5 N6 105.16(14) . . ?
N3 N4 Ni1 112.18(10) . . ?
C6 N4 Ni1 137.47(12) . . ?
C6 N4 N3 105.54(13) . . ?
N5 C7 C8 110.96(16) . . ?
C5 C4 N3 107.54(15) . . ?
C4 C5 C6 105.20(15) . . ?
C9 C8 C7 105.29(16) . . ?
N1 C1 N3 115.38(14) . . ?
N1 C1 N2 127.86(16) . . ?
N2 C1 N3 116.67(14) . . ?
N4 C6 C5 111.20(16) . . ?
N6 C9 C8 107.10(16) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
