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

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

data_up046
_database_code_depnum_ccdc_archive 'CCDC 1495928'
_audit_update_record             
;
2016-07-25 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;

_audit_creation_date             2016-07-25T09:04:55-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C20 H25 Cl N4 Ni'
_chemical_formula_weight         415.6
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.2091(12)
_cell_length_b                   11.2996(5)
_cell_length_c                   16.6840(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1924.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    10894
_cell_measurement_theta_min      3.5916
_cell_measurement_theta_max      32.2039

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.10
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_F_000             872

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.158
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis (Oxford Diffraction)'
_exptl_absorpt_correction_T_min  0.91368
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine-focus sealed tube'
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 CCD
_diffrn_detector_type            'Oxford Diffraction Sapphire 3 CCD'
_diffrn_detector_area_resol_mean 16.0309
_diffrn_orient_matrix_ub_11      0.0500195161
_diffrn_orient_matrix_ub_12      0.0432296195
_diffrn_orient_matrix_ub_13      0.0025981057
_diffrn_orient_matrix_ub_21      0.0185138595
_diffrn_orient_matrix_ub_22      -0.0122892875
_diffrn_orient_matrix_ub_23      -0.0400125978
_diffrn_orient_matrix_ub_31      -0.0443001053
_diffrn_orient_matrix_ub_32      0.0436445302
_diffrn_orient_matrix_ub_33      -0.013833575
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         2
_diffrn_standards_interval_count 50
_diffrn_standards_decay_%        <2%
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_number            23494
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.606
_diffrn_reflns_theta_max         32.364
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.933
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.908
_reflns_Friedel_coverage         0.75
_reflns_number_total             6426
_reflns_number_gt                4820
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlis (Oxford Diffraction)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    WinGX
_computing_publication_material  WinGX

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0428P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6426
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.031
_refine_ls_wR_factor_ref         0.071
_refine_ls_wR_factor_gt          0.0686
_refine_ls_goodness_of_fit_ref   0.908
_refine_ls_restrained_S_all      0.908
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1767 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
 Disorder in one of the butyl side chains modelled in SHELX, 
 and refines satisfactorily to 0.576(1) for major conformer. 
;
_refine_ls_abs_structure_Flack   0.001(4)
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.045

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;  
  No constraints or restraints, except those involving the usual bias
  in H-atom positions, were used.
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6584(2) 0.9461(2) 0.29373(13) 0.0396(5) Uani 1 1 d . . . . .
C3 C 0.5554(3) 1.0805(3) 0.37130(17) 0.0549(7) Uani 1 1 d . . . . .
H3A H 0.5011 1.1428 0.3862 0.066 Uiso 1 1 calc R U . . .
C4 C 0.6321(3) 1.0175(3) 0.42004(16) 0.0537(7) Uani 1 1 d . . . . .
H4A H 0.6418 1.0274 0.4751 0.064 Uiso 1 1 calc R U . . .
C6 C 0.7859(2) 0.8460(2) 0.38865(14) 0.0454(6) Uani 1 1 d . . . . .
C7 C 0.8172(2) 0.7886(2) 0.31820(14) 0.0426(5) Uani 1 1 d . . . . .
C8 C 0.9117(3) 0.7013(2) 0.32146(16) 0.0484(6) Uani 1 1 d . . . . .
C9 C 0.9736(3) 0.6702(3) 0.39201(19) 0.0628(7) Uani 1 1 d . . . . .
H9A H 1.0375 0.6115 0.3929 0.075 Uiso 1 1 calc R U . . .
C10 C 0.9379(3) 0.7288(3) 0.46096(19) 0.0698(9) Uani 1 1 d . . . . .
H10A H 0.9781 0.7083 0.509 0.084 Uiso 1 1 calc R U . . .
C11 C 0.8440(3) 0.8173(3) 0.46110(16) 0.0613(7) Uani 1 1 d . . . . .
H11A H 0.8208 0.856 0.5082 0.074 Uiso 1 1 calc R U . . .
C13 C 0.8586(2) 0.7063(2) 0.18431(15) 0.0428(5) Uani 1 1 d . . . . .
C15 C 0.9928(3) 0.5661(3) 0.1359(2) 0.0655(8) Uani 1 1 d . . . . .
H15A H 1.0343 0.5163 0.0994 0.079 Uiso 1 1 calc R U . . .
C16 C 1.0144(3) 0.5699(3) 0.2146(2) 0.0620(7) Uani 1 1 d . . . . .
H16A H 1.0731 0.5239 0.2437 0.074 Uiso 1 1 calc R U . . .
C17 C 0.5058(2) 1.0874(2) 0.22537(17) 0.0507(6) Uani 1 1 d . . . . .
H17A H 0.4227 1.1207 0.2423 0.061 Uiso 0.576(10) 1 calc R U P A 1
H17B H 0.4875 1.0252 0.1869 0.061 Uiso 0.576(10) 1 calc R U P A 1
H17C H 0.4118 1.087 0.234 0.061 Uiso 0.424(10) 1 calc R U P A 2
H17D H 0.5243 1.0403 0.1781 0.061 Uiso 0.424(10) 1 calc R U P A 2
C18A C 0.5838(11) 1.1804(9) 0.1861(5) 0.079(2) Uani 0.576(10) 1 d . . P A 1
H18A H 0.5798 1.1585 0.1299 0.095 Uiso 0.576(10) 1 calc R U P A 1
H18B H 0.5285 1.2498 0.1909 0.095 Uiso 0.576(10) 1 calc R U P A 1
C19A C 0.6980(6) 1.2223(5) 0.1932(3) 0.0580(18) Uani 0.576(10) 1 d . . P A 1
H19A H 0.7536 1.1703 0.1619 0.07 Uiso 0.576(10) 1 calc R U P A 1
H19B H 0.7217 1.2092 0.2488 0.07 Uiso 0.576(10) 1 calc R U P A 1
C20A C 0.7425(14) 1.3397(10) 0.1752(7) 0.079(3) Uani 0.576(10) 1 d . . P A 1
H20A H 0.763 1.3453 0.1192 0.094 Uiso 0.576(10) 1 calc R U P A 1
H20B H 0.8194 1.3568 0.2062 0.094 Uiso 0.576(10) 1 calc R U P A 1
H20C H 0.6749 1.3956 0.1883 0.094 Uiso 0.576(10) 1 calc R U P A 1
C18B C 0.5533(8) 1.2159(7) 0.2120(6) 0.0459(19) Uani 0.424(10) 1 d . . P A 2
H18C H 0.5551 1.2233 0.154 0.055 Uiso 0.424(10) 1 calc R U P A 2
H18D H 0.4793 1.2633 0.2292 0.055 Uiso 0.424(10) 1 calc R U P A 2
C19B C 0.6419(9) 1.2704(7) 0.2321(5) 0.060(3) Uani 0.424(10) 1 d . . P A 2
H19C H 0.7086 1.2136 0.2473 0.072 Uiso 0.424(10) 1 calc R U P A 2
H19D H 0.6154 1.3098 0.2811 0.072 Uiso 0.424(10) 1 calc R U P A 2
C20B C 0.7164(16) 1.3705(12) 0.1784(13) 0.076(4) Uani 0.424(10) 1 d . . P A 2
H20D H 0.7735 1.3324 0.1406 0.091 Uiso 0.424(10) 1 calc R U P A 2
H20E H 0.7668 1.421 0.2129 0.091 Uiso 0.424(10) 1 calc R U P A 2
H20F H 0.6527 1.4169 0.1501 0.091 Uiso 0.424(10) 1 calc R U P A 2
C21 C 0.8544(3) 0.6687(3) 0.03566(16) 0.0562(6) Uani 1 1 d . . . . .
H21A H 0.9275 0.6973 0.004 0.067 Uiso 1 1 calc R U . . .
H21B H 0.7873 0.7295 0.0356 0.067 Uiso 1 1 calc R U . . .
C22 C 0.7995(3) 0.5565(3) -0.0032(2) 0.0719(9) Uani 1 1 d . . . . .
H22A H 0.8655 0.4949 -0.0014 0.086 Uiso 1 1 calc R U . . .
H22B H 0.7244 0.5295 0.0274 0.086 Uiso 1 1 calc R U . . .
C23 C 0.7585(4) 0.5762(3) -0.08928(19) 0.0749(8) Uani 1 1 d . . . . .
H23A H 0.8291 0.6156 -0.1176 0.09 Uiso 1 1 calc R U . . .
H23B H 0.7443 0.5 -0.1146 0.09 Uiso 1 1 calc R U . . .
C24 C 0.6381(4) 0.6478(4) -0.0969(2) 0.0902(12) Uani 1 1 d . . . . .
H24A H 0.5739 0.6201 -0.0593 0.108 Uiso 1 1 calc R U . . .
H24B H 0.6042 0.6406 -0.1504 0.108 Uiso 1 1 calc R U . . .
H24C H 0.658 0.7293 -0.086 0.108 Uiso 1 1 calc R U . . .
N2 N 0.5716(2) 1.03622(18) 0.29460(12) 0.0439(5) Uani 1 1 d . . . . .
N5 N 0.6935(2) 0.93570(19) 0.37309(12) 0.0446(5) Uani 1 1 d . . . . .
N12 N 0.9324(2) 0.6553(2) 0.24368(13) 0.0491(5) Uani 1 1 d . . . . .
N14 N 0.8983(2) 0.64865(19) 0.11791(14) 0.0499(5) Uani 1 1 d . . . . .
Cl Cl 0.66025(8) 0.89046(7) 0.10455(4) 0.0662(2) Uani 1 1 d . . . . .
Ni Ni 0.74412(3) 0.83355(2) 0.22154(2) 0.03578(8) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.349(3) . ?
C1 N5 1.377(3) . ?
C1 Ni 1.958(2) . ?
C3 C4 1.335(4) . ?
C3 N2 1.384(3) . ?
C3 H3A 0.93 . ?
C4 N5 1.364(3) . ?
C4 H4A 0.93 . ?
C6 C7 1.380(4) . ?
C6 C11 1.385(4) . ?
C6 N5 1.409(3) . ?
C7 C8 1.381(4) . ?
C7 Ni 1.848(2) . ?
C8 C9 1.381(4) . ?
C8 N12 1.414(3) . ?
C9 C10 1.376(5) . ?
C9 H9A 0.93 . ?
C10 C11 1.385(5) . ?
C10 H10A 0.93 . ?
C11 H11A 0.93 . ?
C13 N14 1.347(3) . ?
C13 N12 1.371(3) . ?
C13 Ni 1.954(3) . ?
C15 C16 1.332(5) . ?
C15 N14 1.375(3) . ?
C15 H15A 0.93 . ?
C16 N12 1.367(3) . ?
C16 H16A 0.93 . ?
C17 N2 1.456(3) . ?
C17 C18A 1.472(9) . ?
C17 C18B 1.547(10) . ?
C17 H17A 0.97 . ?
C17 H17B 0.97 . ?
C17 H17C 0.97 . ?
C17 H17D 0.97 . ?
C18A C19A 1.264(10) . ?
C18A H18A 0.97 . ?
C18A H18B 0.97 . ?
C19A C20A 1.434(14) . ?
C19A H19A 0.97 . ?
C19A H19B 0.97 . ?
C20A H20A 0.96 . ?
C20A H20B 0.96 . ?
C20A H20C 0.96 . ?
C18B C19B 1.145(12) . ?
C18B H18C 0.97 . ?
C18B H18D 0.97 . ?
C19B C20B 1.631(19) . ?
C19B H19C 0.97 . ?
C19B H19D 0.97 . ?
C20B H20D 0.96 . ?
C20B H20E 0.96 . ?
C20B H20F 0.96 . ?
C21 N14 1.461(3) . ?
C21 C22 1.530(4) . ?
C21 H21A 0.97 . ?
C21 H21B 0.97 . ?
C22 C23 1.512(5) . ?
C22 H22A 0.97 . ?
C22 H22B 0.97 . ?
C23 C24 1.477(5) . ?
C23 H23A 0.97 . ?
C23 H23B 0.97 . ?
C24 H24A 0.96 . ?
C24 H24B 0.96 . ?
C24 H24C 0.96 . ?
Cl Ni 2.2263(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
N2 C1 N5 103.0(2) . . ?
N2 C1 Ni 142.20(18) . . ?
N5 C1 Ni 114.79(18) . . ?
C4 C3 N2 107.5(2) . . ?
C4 C3 H3A 126.3 . . ?
N2 C3 H3A 126.3 . . ?
C3 C4 N5 106.3(2) . . ?
C3 C4 H4A 126.8 . . ?
N5 C4 H4A 126.8 . . ?
C7 C6 C11 122.3(2) . . ?
C7 C6 N5 109.6(2) . . ?
C11 C6 N5 128.0(2) . . ?
C8 C7 C6 117.6(2) . . ?
C8 C7 Ni 120.8(2) . . ?
C6 C7 Ni 121.4(2) . . ?
C7 C8 C9 122.3(3) . . ?
C7 C8 N12 109.3(2) . . ?
C9 C8 N12 128.3(3) . . ?
C10 C9 C8 117.9(3) . . ?
C10 C9 H9A 121 . . ?
C8 C9 H9A 121 . . ?
C9 C10 C11 122.2(3) . . ?
C9 C10 H10A 118.9 . . ?
C11 C10 H10A 118.9 . . ?
C10 C11 C6 117.6(3) . . ?
C10 C11 H11A 121.2 . . ?
C6 C11 H11A 121.2 . . ?
N14 C13 N12 103.0(2) . . ?
N14 C13 Ni 142.83(19) . . ?
N12 C13 Ni 114.07(18) . . ?
C16 C15 N14 108.0(3) . . ?
C16 C15 H15A 126 . . ?
N14 C15 H15A 126 . . ?
C15 C16 N12 105.8(3) . . ?
C15 C16 H16A 127.1 . . ?
N12 C16 H16A 127.1 . . ?
N2 C17 C18A 112.8(4) . . ?
N2 C17 C18B 110.1(4) . . ?
N2 C17 H17A 109 . . ?
C18A C17 H17A 109 . . ?
N2 C17 H17B 109 . . ?
C18A C17 H17B 109 . . ?
H17A C17 H17B 107.8 . . ?
N2 C17 H17C 109.6 . . ?
C18B C17 H17C 109.7 . . ?
N2 C17 H17D 109.6 . . ?
C18B C17 H17D 109.7 . . ?
H17C C17 H17D 108.2 . . ?
C19A C18A C17 136.5(6) . . ?
C19A C18A H18A 103 . . ?
C17 C18A H18A 103 . . ?
C19A C18A H18B 103 . . ?
C17 C18A H18B 103 . . ?
H18A C18A H18B 105.1 . . ?
C18A C19A C20A 128.3(8) . . ?
C18A C19A H19A 105.2 . . ?
C20A C19A H19A 105.2 . . ?
C18A C19A H19B 105.2 . . ?
C20A C19A H19B 105.2 . . ?
H19A C19A H19B 105.9 . . ?
C19A C20A H20A 109.5 . . ?
C19A C20A H20B 109.5 . . ?
H20A C20A H20B 109.5 . . ?
C19A C20A H20C 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
C19B C18B C17 135.3(8) . . ?
C19B C18B H18C 103.4 . . ?
C17 C18B H18C 103.4 . . ?
C19B C18B H18D 103.4 . . ?
C17 C18B H18D 103.4 . . ?
H18C C18B H18D 105.2 . . ?
C18B C19B C20B 125.5(10) . . ?
C18B C19B H19C 106 . . ?
C20B C19B H19C 106 . . ?
C18B C19B H19D 106 . . ?
C20B C19B H19D 106 . . ?
H19C C19B H19D 106.3 . . ?
C19B C20B H20D 109.5 . . ?
C19B C20B H20E 109.5 . . ?
H20D C20B H20E 109.5 . . ?
C19B C20B H20F 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?
N14 C21 C22 112.5(3) . . ?
N14 C21 H21A 109.1 . . ?
C22 C21 H21A 109.1 . . ?
N14 C21 H21B 109.1 . . ?
C22 C21 H21B 109.1 . . ?
H21A C21 H21B 107.8 . . ?
C23 C22 C21 112.5(3) . . ?
C23 C22 H22A 109.1 . . ?
C21 C22 H22A 109.1 . . ?
C23 C22 H22B 109.1 . . ?
C21 C22 H22B 109.1 . . ?
H22A C22 H22B 107.8 . . ?
C24 C23 C22 113.1(3) . . ?
C24 C23 H23A 109 . . ?
C22 C23 H23A 109 . . ?
C24 C23 H23B 109 . . ?
C22 C23 H23B 109 . . ?
H23A C23 H23B 107.8 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1 N2 C3 111.2(2) . . ?
C1 N2 C17 126.4(2) . . ?
C3 N2 C17 122.3(2) . . ?
C4 N5 C1 112.0(2) . . ?
C4 N5 C6 133.6(2) . . ?
C1 N5 C6 114.4(2) . . ?
C16 N12 C13 112.1(2) . . ?
C16 N12 C8 132.6(2) . . ?
C13 N12 C8 115.3(2) . . ?
C13 N14 C15 111.1(2) . . ?
C13 N14 C21 127.2(2) . . ?
C15 N14 C21 121.7(2) . . ?
C7 Ni C13 80.44(11) . . ?
C7 Ni C1 79.76(11) . . ?
C13 Ni C1 160.18(10) . . ?
C7 Ni Cl 178.64(8) . . ?
C13 Ni Cl 99.43(7) . . ?
C1 Ni Cl 100.35(7) . . ?

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
N2 C3 C4 N5 -0.2(3) . . . . ?
C11 C6 C7 C8 -1.1(4) . . . . ?
N5 C6 C7 C8 176.9(2) . . . . ?
C11 C6 C7 Ni -177.0(2) . . . . ?
N5 C6 C7 Ni 1.1(3) . . . . ?
C6 C7 C8 C9 0.4(4) . . . . ?
Ni C7 C8 C9 176.2(2) . . . . ?
C6 C7 C8 N12 -178.5(2) . . . . ?
Ni C7 C8 N12 -2.7(3) . . . . ?
C7 C8 C9 C10 0.5(4) . . . . ?
N12 C8 C9 C10 179.2(3) . . . . ?
C8 C9 C10 C11 -0.6(5) . . . . ?
C9 C10 C11 C6 -0.1(5) . . . . ?
C7 C6 C11 C10 1.0(4) . . . . ?
N5 C6 C11 C10 -176.7(3) . . . . ?
N14 C15 C16 N12 -0.1(4) . . . . ?
N2 C17 C18A C19A 6.3(16) . . . . ?
C17 C18A C19A C20A -151.5(11) . . . . ?
N2 C17 C18B C19B 18.4(12) . . . . ?
C17 C18B C19B C20B 144.1(10) . . . . ?
N14 C21 C22 C23 -178.0(3) . . . . ?
C21 C22 C23 C24 -72.0(4) . . . . ?
N5 C1 N2 C3 0.8(3) . . . . ?
Ni C1 N2 C3 -179.2(2) . . . . ?
N5 C1 N2 C17 178.0(2) . . . . ?
Ni C1 N2 C17 -2.1(4) . . . . ?
C4 C3 N2 C1 -0.4(3) . . . . ?
C4 C3 N2 C17 -177.7(2) . . . . ?
C18A C17 N2 C1 -86.0(6) . . . . ?
C18B C17 N2 C1 -113.2(4) . . . . ?
C18A C17 N2 C3 90.8(6) . . . . ?
C18B C17 N2 C3 63.7(4) . . . . ?
C3 C4 N5 C1 0.7(3) . . . . ?
C3 C4 N5 C6 179.2(2) . . . . ?
N2 C1 N5 C4 -0.9(3) . . . . ?
Ni C1 N5 C4 179.08(17) . . . . ?
N2 C1 N5 C6 -179.73(18) . . . . ?
Ni C1 N5 C6 0.3(3) . . . . ?
C7 C6 N5 C4 -179.3(3) . . . . ?
C11 C6 N5 C4 -1.4(4) . . . . ?
C7 C6 N5 C1 -0.8(3) . . . . ?
C11 C6 N5 C1 177.1(3) . . . . ?
C15 C16 N12 C13 0.0(4) . . . . ?
C15 C16 N12 C8 -178.8(3) . . . . ?
N14 C13 N12 C16 0.1(3) . . . . ?
Ni C13 N12 C16 -177.74(19) . . . . ?
N14 C13 N12 C8 179.1(2) . . . . ?
Ni C13 N12 C8 1.2(3) . . . . ?
C7 C8 N12 C16 179.5(3) . . . . ?
C9 C8 N12 C16 0.6(5) . . . . ?
C7 C8 N12 C13 0.7(3) . . . . ?
C9 C8 N12 C13 -178.1(3) . . . . ?
N12 C13 N14 C15 -0.1(3) . . . . ?
Ni C13 N14 C15 176.6(3) . . . . ?
N12 C13 N14 C21 -178.4(3) . . . . ?
Ni C13 N14 C21 -1.7(5) . . . . ?
C16 C15 N14 C13 0.1(4) . . . . ?
C16 C15 N14 C21 178.5(3) . . . . ?
C22 C21 N14 C13 -123.6(3) . . . . ?
C22 C21 N14 C15 58.3(4) . . . . ?
C8 C7 Ni C13 2.7(2) . . . . ?
C6 C7 Ni C13 178.4(2) . . . . ?
C8 C7 Ni C1 -176.5(2) . . . . ?
C6 C7 Ni C1 -0.8(2) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_mono
_database_code_depnum_ccdc_archive 'CCDC 1496418'

_audit_update_record             
;
2016-07-27 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;
_publcif_datablock.id            {bc05e78d-a0d1-4a9f-9c43-a4478a410db5}

# start Validation Reply Form
_vrf_PLAT029_mono                
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.950 Note  
RESPONSE: Likely affected by crystal size
;
# end Validation Reply Form

_audit_creation_date             2016-07-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H28 N5 Ni, F6 P'
_chemical_formula_sum            'C22 H28 F6 N5 Ni P'
_chemical_formula_weight         566.17
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.0649(8)
_cell_length_b                   11.8003(9)
_cell_length_c                   22.1082(17)
_cell_angle_alpha                90
_cell_angle_beta                 92.820(3)
_cell_angle_gamma                90
_cell_volume                     2362.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9796
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.84
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.958
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5743
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1214 before and 0.0411 after correction.
The Ratio of minimum to maximum transmission is 0.7701.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_Laue_measured_fraction_full 0.950
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14192
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.392
_diffrn_reflns_theta_min         2.249
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4313
_reflns_number_total             5426
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.415
_refine_diff_density_min         -0.592
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         5426
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0394
_refine_ls_restrained_S_all      1.030
_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)+(0.0323P)²+2.1626P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0931
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,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), C4(H4A,H4B), C17(H17A,H17B), C18(H18A,H18B),
 C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_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 0.23288(3) 0.50685(2) 0.47207(2) 0.01105(8) Uani 1 1 d . . . . .
N1 N 0.07837(19) 0.69563(15) 0.54271(8) 0.0135(4) Uani 1 1 d . . . . .
N2 N 0.22514(19) 0.58378(16) 0.59242(8) 0.0147(4) Uani 1 1 d . . . . .
N3 N 0.4282(2) 0.32316(15) 0.47003(9) 0.0166(4) Uani 1 1 d . . . . .
N4 N 0.3467(2) 0.33498(16) 0.37791(9) 0.0176(4) Uani 1 1 d . . . . .
N5 N 0.1188(2) 0.56501(15) 0.40499(8) 0.0148(4) Uani 1 1 d . . . . .
C1 C -0.2919(3) 0.9890(2) 0.46835(11) 0.0246(5) Uani 1 1 d . . . . .
H1A H -0.3492 1.0094 0.4323 0.037 Uiso 1 1 calc GR . . . .
H1B H -0.2345 1.0531 0.4824 0.037 Uiso 1 1 calc GR . . . .
H1C H -0.3568 0.9661 0.4991 0.037 Uiso 1 1 calc GR . . . .
C2 C -0.1890(2) 0.89142(19) 0.45441(10) 0.0179(5) Uani 1 1 d . . . . .
H2A H -0.2467 0.8299 0.4363 0.022 Uiso 1 1 calc R . . . .
H2B H -0.1199 0.9166 0.4250 0.022 Uiso 1 1 calc R . . . .
C3 C -0.1028(2) 0.84754(18) 0.51032(10) 0.0150(4) Uani 1 1 d . . . . .
H3A H -0.0398 0.9070 0.5275 0.018 Uiso 1 1 calc R . . . .
H3B H -0.1706 0.8244 0.5406 0.018 Uiso 1 1 calc R . . . .
C4 C -0.0100(2) 0.74781(19) 0.49245(9) 0.0151(4) Uani 1 1 d . . . . .
H4A H -0.0747 0.6905 0.4741 0.018 Uiso 1 1 calc R . . . .
H4B H 0.0562 0.7726 0.4619 0.018 Uiso 1 1 calc R . . . .
C5 C 0.1674(2) 0.60533(18) 0.53529(10) 0.0135(4) Uani 1 1 d . . . . .
C6 C 0.0806(2) 0.7289(2) 0.60317(10) 0.0181(5) Uani 1 1 d . . . . .
H6 H 0.0281 0.7887 0.6191 0.022 Uiso 1 1 calc R . . . .
C7 C 0.1733(2) 0.6583(2) 0.63427(10) 0.0183(5) Uani 1 1 d . . . . .
H7 H 0.1974 0.6596 0.6756 0.022 Uiso 1 1 calc R . . . .
C8 C 0.3266(2) 0.49199(19) 0.59552(10) 0.0165(4) Uani 1 1 d . . . . .
C9 C 0.4039(2) 0.4486(2) 0.64624(11) 0.0203(5) Uani 1 1 d . . . . .
H9 H 0.3930 0.4790 0.6846 0.024 Uiso 1 1 calc R . . . .
C10 C 0.4983(3) 0.3574(2) 0.63727(11) 0.0224(5) Uani 1 1 d . . . . .
H10 H 0.5514 0.3269 0.6705 0.027 Uiso 1 1 calc R . . . .
C11 C 0.5160(2) 0.3106(2) 0.58012(11) 0.0217(5) Uani 1 1 d . . . . .
H11 H 0.5801 0.2503 0.5747 0.026 Uiso 1 1 calc R . . . .
C12 C 0.4343(2) 0.35736(18) 0.53191(10) 0.0158(4) Uani 1 1 d . . . . .
C13 C 0.3399(2) 0.44785(18) 0.53841(10) 0.0147(4) Uani 1 1 d . . . . .
C14 C 0.3350(2) 0.38496(19) 0.43265(10) 0.0153(4) Uani 1 1 d . . . . .
C15 C 0.4951(3) 0.2368(2) 0.44015(12) 0.0232(5) Uani 1 1 d . . . . .
H15 H 0.5622 0.1844 0.4566 0.028 Uiso 1 1 calc R . . . .
C16 C 0.4436(3) 0.2437(2) 0.38220(12) 0.0225(5) Uani 1 1 d . . . . .
H16 H 0.4683 0.1960 0.3507 0.027 Uiso 1 1 calc R . . . .
C17 C 0.2715(3) 0.3744(2) 0.32149(10) 0.0222(5) Uani 1 1 d . . . . .
H17A H 0.2605 0.4561 0.3234 0.027 Uiso 1 1 calc R . . . .
H17B H 0.1734 0.3416 0.3182 0.027 Uiso 1 1 calc R . . . .
C18 C 0.3526(3) 0.3443(2) 0.26529(11) 0.0220(5) Uani 1 1 d . . . . .
H18A H 0.3465 0.2631 0.2587 0.026 Uiso 1 1 calc R . . . .
H18B H 0.4561 0.3640 0.2717 0.026 Uiso 1 1 calc R . . . .
C19 C 0.2894(3) 0.4052(2) 0.20902(11) 0.0250(5) Uani 1 1 d . . . . .
H19A H 0.3365 0.3756 0.1739 0.030 Uiso 1 1 calc R . . . .
H19B H 0.1848 0.3882 0.2041 0.030 Uiso 1 1 calc R . . . .
C20 C 0.3089(3) 0.5331(2) 0.21056(12) 0.0294(6) Uani 1 1 d . . . . .
H20A H 0.2691 0.5651 0.1733 0.044 Uiso 1 1 calc GR . . . .
H20B H 0.4121 0.5510 0.2154 0.044 Uiso 1 1 calc GR . . . .
H20C H 0.2580 0.5639 0.2439 0.044 Uiso 1 1 calc GR . . . .
C21 C 0.0502(2) 0.60217(19) 0.36515(10) 0.0157(4) Uani 1 1 d . . . . .
C22 C -0.0372(3) 0.6503(2) 0.31459(11) 0.0258(6) Uani 1 1 d . . . . .
H22A H -0.0550 0.5934 0.2841 0.039 Uiso 1 1 calc GR . . . .
H22B H 0.0154 0.7126 0.2978 0.039 Uiso 1 1 calc GR . . . .
H22C H -0.1298 0.6768 0.3285 0.039 Uiso 1 1 calc GR . . . .
P1 P 0.21871(6) 0.94756(5) 0.32616(3) 0.01633(14) Uani 1 1 d . . . . .
F1 F 0.08767(16) 0.92575(13) 0.27630(7) 0.0326(4) Uani 1 1 d . . . . .
F2 F 0.3131(2) 0.85455(17) 0.29349(9) 0.0563(5) Uani 1 1 d . . . . .
F3 F 0.1543(2) 0.85168(16) 0.36779(8) 0.0518(5) Uani 1 1 d . . . . .
F4 F 0.28335(19) 1.04269(16) 0.28366(8) 0.0469(5) Uani 1 1 d . . . . .
F5 F 0.1224(2) 1.04017(18) 0.35656(9) 0.0648(6) Uani 1 1 d . . . . .
F6 F 0.3502(2) 0.96782(15) 0.37446(8) 0.0457(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 N5 1.8943(19) . ?
Ni1 C5 1.933(2) . ?
Ni1 C13 1.854(2) . ?
Ni1 C14 1.940(2) . ?
N1 C4 1.472(3) . ?
N1 C5 1.351(3) . ?
N1 C6 1.392(3) . ?
N2 C5 1.367(3) . ?
N2 C7 1.375(3) . ?
N2 C8 1.420(3) . ?
N3 C12 1.425(3) . ?
N3 C14 1.363(3) . ?
N3 C15 1.371(3) . ?
N4 C14 1.355(3) . ?
N4 C16 1.391(3) . ?
N4 C17 1.467(3) . ?
N5 C21 1.141(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.523(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.520(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.510(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C6 H6 0.9300 . ?
C6 C7 1.348(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.390(3) . ?
C8 C13 1.377(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.395(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.396(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.382(3) . ?
C12 C13 1.380(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.344(4) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.517(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.524(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.519(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.454(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
P1 F1 1.6010(15) . ?
P1 F2 1.5872(17) . ?
P1 F3 1.5879(17) . ?
P1 F4 1.5937(16) . ?
P1 F5 1.5703(18) . ?
P1 F6 1.5788(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 Ni1 C5 99.96(8) . . ?
N5 Ni1 C14 99.84(8) . . ?
C5 Ni1 C14 160.14(9) . . ?
C13 Ni1 N5 178.42(9) . . ?
C13 Ni1 C5 79.70(9) . . ?
C13 Ni1 C14 80.46(10) . . ?
C5 N1 C4 122.96(18) . . ?
C5 N1 C6 110.99(18) . . ?
C6 N1 C4 126.04(18) . . ?
C5 N2 C7 112.00(18) . . ?
C5 N2 C8 113.83(18) . . ?
C7 N2 C8 134.15(19) . . ?
C14 N3 C12 115.11(18) . . ?
C14 N3 C15 112.4(2) . . ?
C15 N3 C12 132.5(2) . . ?
C14 N4 C16 110.69(19) . . ?
C14 N4 C17 124.58(18) . . ?
C16 N4 C17 124.70(19) . . ?
C21 N5 Ni1 178.59(19) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 C1 112.84(19) . . ?
C3 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C2 C3 H3A 109.9 . . ?
C2 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
C4 C3 C2 108.85(17) . . ?
C4 C3 H3A 109.9 . . ?
C4 C3 H3B 109.9 . . ?
N1 C4 C3 114.70(17) . . ?
N1 C4 H4A 108.6 . . ?
N1 C4 H4B 108.6 . . ?
C3 C4 H4A 108.6 . . ?
C3 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
N1 C5 Ni1 140.19(16) . . ?
N1 C5 N2 103.78(18) . . ?
N2 C5 Ni1 116.03(15) . . ?
N1 C6 H6 126.4 . . ?
C7 C6 N1 107.1(2) . . ?
C7 C6 H6 126.4 . . ?
N2 C7 H7 127.0 . . ?
C6 C7 N2 106.08(19) . . ?
C6 C7 H7 127.0 . . ?
C9 C8 N2 128.3(2) . . ?
C13 C8 N2 109.28(19) . . ?
C13 C8 C9 122.5(2) . . ?
C8 C9 H9 121.4 . . ?
C8 C9 C10 117.3(2) . . ?
C10 C9 H9 121.4 . . ?
C9 C10 H10 118.9 . . ?
C9 C10 C11 122.2(2) . . ?
C11 C10 H10 118.9 . . ?
C10 C11 H11 121.3 . . ?
C12 C11 C10 117.3(2) . . ?
C12 C11 H11 121.3 . . ?
C11 C12 N3 128.4(2) . . ?
C13 C12 N3 108.90(19) . . ?
C13 C12 C11 122.7(2) . . ?
C8 C13 Ni1 121.16(17) . . ?
C8 C13 C12 118.1(2) . . ?
C12 C13 Ni1 120.74(17) . . ?
N3 C14 Ni1 114.78(16) . . ?
N4 C14 Ni1 141.61(17) . . ?
N4 C14 N3 103.61(18) . . ?
N3 C15 H15 127.1 . . ?
C16 C15 N3 105.9(2) . . ?
C16 C15 H15 127.1 . . ?
N4 C16 H16 126.3 . . ?
C15 C16 N4 107.4(2) . . ?
C15 C16 H16 126.3 . . ?
N4 C17 H17A 108.9 . . ?
N4 C17 H17B 108.9 . . ?
N4 C17 C18 113.47(19) . . ?
H17A C17 H17B 107.7 . . ?
C18 C17 H17A 108.9 . . ?
C18 C17 H17B 108.9 . . ?
C17 C18 H18A 109.1 . . ?
C17 C18 H18B 109.1 . . ?
C17 C18 C19 112.3(2) . . ?
H18A C18 H18B 107.9 . . ?
C19 C18 H18A 109.1 . . ?
C19 C18 H18B 109.1 . . ?
C18 C19 H19A 108.7 . . ?
C18 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
C20 C19 C18 114.3(2) . . ?
C20 C19 H19A 108.7 . . ?
C20 C19 H19B 108.7 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N5 C21 C22 179.6(2) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
F2 P1 F1 88.51(10) . . ?
F2 P1 F3 89.59(12) . . ?
F2 P1 F4 89.82(11) . . ?
F3 P1 F1 90.17(9) . . ?
F3 P1 F4 179.27(11) . . ?
F4 P1 F1 89.39(8) . . ?
F5 P1 F1 89.84(10) . . ?
F5 P1 F2 178.20(11) . . ?
F5 P1 F3 91.13(12) . . ?
F5 P1 F4 89.45(12) . . ?
F5 P1 F6 91.28(11) . . ?
F6 P1 F1 178.83(10) . . ?
F6 P1 F2 90.37(11) . . ?
F6 P1 F3 90.16(9) . . ?
F6 P1 F4 90.28(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C6 C7 N2 -0.1(2) . . . . ?
N2 C8 C9 C10 -179.7(2) . . . . ?
N2 C8 C13 Ni1 -0.7(3) . . . . ?
N2 C8 C13 C12 179.94(18) . . . . ?
N3 C12 C13 Ni1 -1.0(2) . . . . ?
N3 C12 C13 C8 178.30(19) . . . . ?
N3 C15 C16 N4 0.4(3) . . . . ?
N4 C17 C18 C19 -168.8(2) . . . . ?
C1 C2 C3 C4 177.31(19) . . . . ?
C2 C3 C4 N1 -179.26(18) . . . . ?
C4 N1 C5 Ni1 1.9(4) . . . . ?
C4 N1 C5 N2 -178.98(18) . . . . ?
C4 N1 C6 C7 178.9(2) . . . . ?
C5 Ni1 C13 C8 0.90(18) . . . . ?
C5 Ni1 C13 C12 -179.78(19) . . . . ?
C5 N1 C4 C3 179.69(19) . . . . ?
C5 N1 C6 C7 0.2(3) . . . . ?
C5 N2 C7 C6 -0.1(3) . . . . ?
C5 N2 C8 C9 -179.9(2) . . . . ?
C5 N2 C8 C13 -0.1(3) . . . . ?
C6 N1 C4 C3 1.1(3) . . . . ?
C6 N1 C5 Ni1 -179.4(2) . . . . ?
C6 N1 C5 N2 -0.2(2) . . . . ?
C7 N2 C5 Ni1 179.58(14) . . . . ?
C7 N2 C5 N1 0.2(2) . . . . ?
C7 N2 C8 C9 1.7(4) . . . . ?
C7 N2 C8 C13 -178.5(2) . . . . ?
C8 N2 C5 Ni1 0.8(2) . . . . ?
C8 N2 C5 N1 -178.65(17) . . . . ?
C8 N2 C7 C6 178.4(2) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C9 C8 C13 Ni1 179.10(17) . . . . ?
C9 C8 C13 C12 -0.2(3) . . . . ?
C9 C10 C11 C12 -0.6(4) . . . . ?
C10 C11 C12 N3 -177.6(2) . . . . ?
C10 C11 C12 C13 0.9(3) . . . . ?
C11 C12 C13 Ni1 -179.85(17) . . . . ?
C11 C12 C13 C8 -0.5(3) . . . . ?
C12 N3 C14 Ni1 0.6(2) . . . . ?
C12 N3 C14 N4 -178.73(17) . . . . ?
C12 N3 C15 C16 177.9(2) . . . . ?
C13 C8 C9 C10 0.5(3) . . . . ?
C14 Ni1 C13 C8 -178.24(19) . . . . ?
C14 Ni1 C13 C12 1.08(18) . . . . ?
C14 N3 C12 C11 179.0(2) . . . . ?
C14 N3 C12 C13 0.2(3) . . . . ?
C14 N3 C15 C16 0.1(3) . . . . ?
C14 N4 C16 C15 -0.8(3) . . . . ?
C14 N4 C17 C18 152.5(2) . . . . ?
C15 N3 C12 C11 1.2(4) . . . . ?
C15 N3 C12 C13 -177.5(2) . . . . ?
C15 N3 C14 Ni1 178.74(15) . . . . ?
C15 N3 C14 N4 -0.5(2) . . . . ?
C16 N4 C14 Ni1 -178.2(2) . . . . ?
C16 N4 C14 N3 0.8(2) . . . . ?
C16 N4 C17 C18 -25.1(3) . . . . ?
C17 N4 C14 Ni1 3.9(4) . . . . ?
C17 N4 C14 N3 -177.2(2) . . . . ?
C17 N4 C16 C15 177.2(2) . . . . ?
C17 C18 C19 C20 65.7(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Vapour deposition'
_chemical_properties_physical    ', Moisture-sensitive'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# 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_orth
_database_code_depnum_ccdc_archive 'CCDC 1496419'
_audit_update_record             
;
2016-07-27 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;
_publcif_datablock.id            {1975d308-8449-4c55-9645-82b7f68ab83e}

# start Validation Reply Form
_vrf_PLAT987_orth                
;
PROBLEM: The Flack x is >> 0 -  Do a BASF/TWIN Refinement     Please Check
RESPONSE: A BASF/TWIN refinement didn't improve the structure 
;
# end Validation Reply Form

_audit_creation_date             2016-07-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H25 Cl N4 Ni'
_chemical_formula_sum            'C20 H25 Cl N4 Ni'
_chemical_formula_weight         415.60
_chemical_absolute_configuration syn
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   9.8944(11)
_cell_length_b                   11.3015(13)
_cell_length_c                   16.6259(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1859.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9842
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.207
_cell_measurement_theta_min      2.179
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.199
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5424
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1256 before and 0.0797 after correction.
The Ratio of minimum to maximum transmission is 0.7274.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.23
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0839
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            57709
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.405
_diffrn_reflns_theta_min         2.179
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                4251
_reflns_number_total             4645
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.420
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 
;
 Flack x determined using 1706 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.034(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4645
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0307
_refine_ls_restrained_S_all      1.063
_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)+(0.0256P)²+0.7660P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0608
_refine_ls_wR_factor_ref         0.0628
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C18A-C17 \\sim C18B-C17 \\sim C19A-C18A \\sim C19B-C18B \\sim C19B-C20B \\sim
C20A-C19A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C18A) = Uanis(C18B) = Uanis(C19B) = Uanis(C19A) = Uanis(C20A) =
Uanis(C20B)
4. Others
 Sof(H17C)=Sof(H17D)=Sof(C18B)=Sof(H18C)=Sof(H18D)=Sof(C19B)=Sof(H19C)=
 Sof(H19D)=Sof(C20B)=Sof(H20D)=Sof(H20E)=Sof(H20F)=1-FVAR(1)
 Sof(H17A)=Sof(H17B)=Sof(C18A)=Sof(H18A)=Sof(H18B)=Sof(C19A)=Sof(H19A)=
 Sof(H19B)=Sof(C20A)=Sof(H20A)=Sof(H20B)=Sof(H20C)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C3(H3A,H3B), C2(H2A,H2B), C17(H17A,H17B), C17(H17C,H17D),
 C18A(H18A,H18B), C19A(H19A,H19B), C18B(H18C,H18D), C19B(H19C,H19D)
5.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C10(H10), C9(H9), C6(H6), C7(H7), C15(H15), C16(H16)
5.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C20A(H20A,H20B,H20C), C20B(H20D,H20E,H20F)
;
_atom_sites_solution_hydrogens   geom
_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 0.76028(3) 0.67054(3) 0.27612(2) 0.00918(9) Uani 1 1 d . . . . .
Cl1 Cl 0.84701(7) 0.61040(6) 0.39306(4) 0.01785(16) Uani 1 1 d . . . . .
N2 N 0.5638(2) 0.8482(2) 0.25579(14) 0.0143(5) Uani 1 1 d . . . . .
N1 N 0.6042(2) 0.8560(2) 0.38174(15) 0.0146(5) Uani 1 1 d . . . . .
N3 N 0.8073(2) 0.5680(2) 0.12394(14) 0.0110(5) Uani 1 1 d . . . . .
N4 N 0.9312(2) 0.4640(2) 0.20198(13) 0.0113(5) Uani 1 1 d . . . . .
C13 C 0.6823(3) 0.7159(2) 0.17956(17) 0.0117(5) Uani 1 1 d . . . . .
C12 C 0.7127(3) 0.6588(2) 0.10849(17) 0.0131(5) Uani 1 1 d . . . . .
C11 C 0.6510(3) 0.6872(3) 0.03615(17) 0.0166(6) Uani 1 1 d . . . . .
H11 H 0.6743 0.6487 -0.0113 0.020 Uiso 1 1 calc R . . . .
C10 C 0.5527(3) 0.7754(3) 0.03712(19) 0.0207(7) Uani 1 1 d . . . . .
H10 H 0.5101 0.7958 -0.0108 0.025 Uiso 1 1 calc R . . . .
C9 C 0.5163(3) 0.8340(3) 0.10754(19) 0.0197(6) Uani 1 1 d . . . . .
H9 H 0.4495 0.8918 0.1077 0.024 Uiso 1 1 calc R . . . .
C8 C 0.5836(3) 0.8026(2) 0.17737(18) 0.0138(6) Uani 1 1 d . . . . .
C5 C 0.6434(3) 0.7979(2) 0.31456(17) 0.0132(6) Uani 1 1 d . . . . .
C4 C 0.6531(3) 0.8371(3) 0.46414(16) 0.0161(6) Uani 1 1 d . . . . .
H4A H 0.7244 0.7782 0.4634 0.019 Uiso 1 1 calc R . . . .
H4B H 0.5798 0.8067 0.4969 0.019 Uiso 1 1 calc R . . . .
C3 C 0.7069(3) 0.9500(3) 0.50195(19) 0.0189(6) Uani 1 1 d . . . . .
H3A H 0.7844 0.9775 0.4715 0.023 Uiso 1 1 calc R . . . .
H3B H 0.6378 1.0108 0.4994 0.023 Uiso 1 1 calc R . . . .
C2 C 0.7479(3) 0.9311(3) 0.58882(17) 0.0201(6) Uani 1 1 d . . . . .
H2A H 0.6737 0.8938 0.6173 0.024 Uiso 1 1 calc R . . . .
H2B H 0.7641 1.0075 0.6136 0.024 Uiso 1 1 calc R . . . .
C1 C 0.8739(3) 0.8550(3) 0.5984(2) 0.0250(7) Uani 1 1 d . . . . .
H1A H 0.8567 0.7773 0.5774 0.037 Uiso 1 1 calc GR . . . .
H1B H 0.8970 0.8494 0.6544 0.037 Uiso 1 1 calc GR . . . .
H1C H 0.9475 0.8904 0.5695 0.037 Uiso 1 1 calc GR . . . .
C6 C 0.5033(3) 0.9376(3) 0.3653(2) 0.0207(7) Uani 1 1 d . . . . .
H6 H 0.4609 0.9867 0.4024 0.025 Uiso 1 1 calc R . . . .
C7 C 0.4777(3) 0.9330(3) 0.2858(2) 0.0193(6) Uani 1 1 d . . . . .
H7 H 0.4150 0.9777 0.2573 0.023 Uiso 1 1 calc R . . . .
C15 C 0.8647(3) 0.4821(3) 0.07607(17) 0.0141(6) Uani 1 1 d . . . . .
H15 H 0.8519 0.4713 0.0211 0.017 Uiso 1 1 calc R . . . .
C16 C 0.9430(3) 0.4172(3) 0.12525(17) 0.0142(6) Uani 1 1 d . . . . .
H16 H 0.9956 0.3525 0.1105 0.017 Uiso 1 1 calc R . . . .
C17 C 0.9995(3) 0.4126(2) 0.27191(17) 0.0142(6) Uani 1 1 d D . . . .
H17A H 1.0259 0.4755 0.3083 0.017 Uiso 0.854(5) 1 calc R . P A 1
H17B H 1.0811 0.3726 0.2542 0.017 Uiso 0.854(5) 1 calc R . P A 1
H17C H 0.9846 0.4628 0.3184 0.017 Uiso 0.146(5) 1 calc R . P A 2
H17D H 1.0960 0.4097 0.2618 0.017 Uiso 0.146(5) 1 calc R . P A 2
C18A C 0.9109(3) 0.3255(3) 0.3165(2) 0.0178(5) Uani 0.854(5) 1 d D . P A 1
H18A H 0.8365 0.3685 0.3408 0.021 Uiso 0.854(5) 1 calc R . P A 1
H18B H 0.9633 0.2904 0.3596 0.021 Uiso 0.854(5) 1 calc R . P A 1
C19A C 0.8535(3) 0.2271(3) 0.2647(2) 0.0178(5) Uani 0.854(5) 1 d D . P A 1
H19A H 0.7917 0.2608 0.2257 0.021 Uiso 0.854(5) 1 calc R . P A 1
H19B H 0.9266 0.1894 0.2354 0.021 Uiso 0.854(5) 1 calc R . P A 1
C20A C 0.7797(4) 0.1346(3) 0.3139(2) 0.0178(5) Uani 0.854(5) 1 d D . P A 1
H20A H 0.7459 0.0739 0.2789 0.027 Uiso 0.854(5) 1 calc GR . P A 1
H20B H 0.7055 0.1710 0.3418 0.027 Uiso 0.854(5) 1 calc GR . P A 1
H20C H 0.8407 0.1003 0.3523 0.027 Uiso 0.854(5) 1 calc GR . P A 1
C14 C 0.8457(3) 0.5575(2) 0.20308(16) 0.0113(5) Uani 1 1 d . . . . .
C18B C 0.9485(17) 0.2882(15) 0.2903(14) 0.0178(5) Uani 0.146(5) 1 d D . P A 2
H18C H 0.9738 0.2362 0.2463 0.021 Uiso 0.146(5) 1 calc R . P A 2
H18D H 0.9929 0.2596 0.3385 0.021 Uiso 0.146(5) 1 calc R . P A 2
C19B C 0.7971(17) 0.2813(16) 0.3022(12) 0.0178(5) Uani 0.146(5) 1 d D . P A 2
H19C H 0.7714 0.3390 0.3426 0.021 Uiso 0.146(5) 1 calc R . P A 2
H19D H 0.7534 0.3038 0.2522 0.021 Uiso 0.146(5) 1 calc R . P A 2
C20B C 0.744(2) 0.1624(17) 0.3273(14) 0.0178(5) Uani 0.146(5) 1 d D . P A 2
H20D H 0.7485 0.1086 0.2827 0.027 Uiso 0.146(5) 1 calc GR . P A 2
H20E H 0.6515 0.1702 0.3444 0.027 Uiso 0.146(5) 1 calc GR . P A 2
H20F H 0.7972 0.1323 0.3710 0.027 Uiso 0.146(5) 1 calc GR . P A 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 Cl1 2.2312(8) . ?
Ni1 C13 1.854(3) . ?
Ni1 C5 1.954(3) . ?
Ni1 C14 1.955(3) . ?
N2 C8 1.416(4) . ?
N2 C5 1.378(4) . ?
N2 C7 1.376(4) . ?
N1 C5 1.352(4) . ?
N1 C4 1.468(4) . ?
N1 C6 1.387(4) . ?
N3 C12 1.412(3) . ?
N3 C15 1.378(4) . ?
N3 C14 1.375(3) . ?
N4 C16 1.386(4) . ?
N4 C17 1.465(3) . ?
N4 C14 1.353(4) . ?
C13 C12 1.380(4) . ?
C13 C8 1.383(4) . ?
C12 C11 1.387(4) . ?
C11 H11 0.9300 . ?
C11 C10 1.392(4) . ?
C10 H10 0.9300 . ?
C10 C9 1.392(4) . ?
C9 H9 0.9300 . ?
C9 C8 1.385(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C3 1.518(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C2 1.516(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.523(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C6 H6 0.9300 . ?
C6 C7 1.346(5) . ?
C7 H7 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.344(4) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 H17C 0.9700 . ?
C17 H17D 0.9700 . ?
C17 C18A 1.512(4) . ?
C17 C18B 1.525(15) . ?
C18A H18A 0.9700 . ?
C18A H18B 0.9700 . ?
C18A C19A 1.517(5) . ?
C19A H19A 0.9700 . ?
C19A H19B 0.9700 . ?
C19A C20A 1.515(5) . ?
C20A H20A 0.9600 . ?
C20A H20B 0.9600 . ?
C20A H20C 0.9600 . ?
C18B H18C 0.9700 . ?
C18B H18D 0.9700 . ?
C18B C19B 1.513(17) . ?
C19B H19C 0.9700 . ?
C19B H19D 0.9700 . ?
C19B C20B 1.503(17) . ?
C20B H20D 0.9600 . ?
C20B H20E 0.9600 . ?
C20B H20F 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
C13 Ni1 Cl1 177.55(9) . . ?
C13 Ni1 C5 80.38(12) . . ?
C13 Ni1 C14 79.80(12) . . ?
C5 Ni1 Cl1 99.62(9) . . ?
C5 Ni1 C14 160.15(11) . . ?
C14 Ni1 Cl1 100.12(8) . . ?
C5 N2 C8 115.0(2) . . ?
C7 N2 C8 132.4(3) . . ?
C7 N2 C5 112.5(3) . . ?
C5 N1 C4 127.3(2) . . ?
C5 N1 C6 111.5(2) . . ?
C6 N1 C4 121.2(2) . . ?
C15 N3 C12 132.8(2) . . ?
C14 N3 C12 114.9(2) . . ?
C14 N3 C15 112.2(2) . . ?
C16 N4 C17 122.7(2) . . ?
C14 N4 C16 111.3(2) . . ?
C14 N4 C17 126.0(2) . . ?
C12 C13 Ni1 121.4(2) . . ?
C12 C13 C8 117.6(3) . . ?
C8 C13 Ni1 120.8(2) . . ?
C13 C12 N3 109.2(2) . . ?
C13 C12 C11 122.6(3) . . ?
C11 C12 N3 128.2(3) . . ?
C12 C11 H11 121.2 . . ?
C12 C11 C10 117.6(3) . . ?
C10 C11 H11 121.2 . . ?
C11 C10 H10 119.0 . . ?
C9 C10 C11 122.1(3) . . ?
C9 C10 H10 119.0 . . ?
C10 C9 H9 121.3 . . ?
C8 C9 C10 117.3(3) . . ?
C8 C9 H9 121.3 . . ?
C13 C8 N2 109.4(3) . . ?
C13 C8 C9 122.9(3) . . ?
C9 C8 N2 127.7(3) . . ?
N2 C5 Ni1 114.2(2) . . ?
N1 C5 Ni1 142.9(2) . . ?
N1 C5 N2 102.8(2) . . ?
N1 C4 H4A 109.1 . . ?
N1 C4 H4B 109.1 . . ?
N1 C4 C3 112.3(2) . . ?
H4A C4 H4B 107.9 . . ?
C3 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
C2 C3 C4 111.7(2) . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C3 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
C3 C2 C1 113.5(3) . . ?
H2A C2 H2B 107.7 . . ?
C1 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C6 H6 126.2 . . ?
C7 C6 N1 107.7(3) . . ?
C7 C6 H6 126.2 . . ?
N2 C7 H7 127.3 . . ?
C6 C7 N2 105.5(3) . . ?
C6 C7 H7 127.3 . . ?
N3 C15 H15 127.1 . . ?
C16 C15 N3 105.7(2) . . ?
C16 C15 H15 127.1 . . ?
N4 C16 H16 126.2 . . ?
C15 C16 N4 107.6(2) . . ?
C15 C16 H16 126.2 . . ?
N4 C17 H17A 109.1 . . ?
N4 C17 H17B 109.1 . . ?
N4 C17 H17C 109.3 . . ?
N4 C17 H17D 109.3 . . ?
N4 C17 C18A 112.3(2) . . ?
N4 C17 C18B 111.8(8) . . ?
H17A C17 H17B 107.9 . . ?
H17C C17 H17D 107.9 . . ?
C18A C17 H17A 109.1 . . ?
C18A C17 H17B 109.1 . . ?
C18B C17 H17C 109.3 . . ?
C18B C17 H17D 109.3 . . ?
C17 C18A H18A 108.6 . . ?
C17 C18A H18B 108.6 . . ?
C17 C18A C19A 114.6(3) . . ?
H18A C18A H18B 107.6 . . ?
C19A C18A H18A 108.6 . . ?
C19A C18A H18B 108.6 . . ?
C18A C19A H19A 109.1 . . ?
C18A C19A H19B 109.1 . . ?
H19A C19A H19B 107.9 . . ?
C20A C19A C18A 112.4(3) . . ?
C20A C19A H19A 109.1 . . ?
C20A C19A H19B 109.1 . . ?
C19A C20A H20A 109.5 . . ?
C19A C20A H20B 109.5 . . ?
C19A C20A H20C 109.5 . . ?
H20A C20A H20B 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
N3 C14 Ni1 114.71(19) . . ?
N4 C14 Ni1 142.1(2) . . ?
N4 C14 N3 103.2(2) . . ?
C17 C18B H18C 108.8 . . ?
C17 C18B H18D 108.8 . . ?
H18C C18B H18D 107.7 . . ?
C19B C18B C17 113.7(14) . . ?
C19B C18B H18C 108.8 . . ?
C19B C18B H18D 108.8 . . ?
C18B C19B H19C 108.4 . . ?
C18B C19B H19D 108.4 . . ?
H19C C19B H19D 107.5 . . ?
C20B C19B C18B 115.5(17) . . ?
C20B C19B H19C 108.4 . . ?
C20B C19B H19D 108.4 . . ?
C19B C20B H20D 109.5 . . ?
C19B C20B H20E 109.5 . . ?
C19B C20B H20F 109.5 . . ?
H20D C20B H20E 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 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 C13 C12 N3 -0.3(3) . . . . ?
Ni1 C13 C12 C11 176.8(2) . . . . ?
Ni1 C13 C8 N2 3.0(3) . . . . ?
Ni1 C13 C8 C9 -175.7(2) . . . . ?
N1 C4 C3 C2 176.0(2) . . . . ?
N1 C6 C7 N2 0.1(3) . . . . ?
N3 C12 C11 C10 175.2(3) . . . . ?
N3 C15 C16 N4 0.4(3) . . . . ?
N4 C17 C18A C19A 54.4(4) . . . . ?
N4 C17 C18B C19B -55.5(19) . . . . ?
C13 C12 C11 C10 -1.4(4) . . . . ?
C12 N3 C15 C16 -177.0(3) . . . . ?
C12 N3 C14 Ni1 0.1(3) . . . . ?
C12 N3 C14 N4 178.1(2) . . . . ?
C12 C13 C8 N2 178.3(2) . . . . ?
C12 C13 C8 C9 -0.4(4) . . . . ?
C12 C11 C10 C9 0.0(4) . . . . ?
C11 C10 C9 C8 1.1(4) . . . . ?
C10 C9 C8 N2 -179.3(3) . . . . ?
C10 C9 C8 C13 -0.8(4) . . . . ?
C8 N2 C5 Ni1 -2.3(3) . . . . ?
C8 N2 C5 N1 -179.7(2) . . . . ?
C8 N2 C7 C6 179.1(3) . . . . ?
C8 C13 C12 N3 -175.6(2) . . . . ?
C8 C13 C12 C11 1.6(4) . . . . ?
C5 Ni1 C13 C12 -178.5(2) . . . . ?
C5 Ni1 C13 C8 -3.4(2) . . . . ?
C5 N2 C8 C13 -0.3(3) . . . . ?
C5 N2 C8 C9 178.4(3) . . . . ?
C5 N2 C7 C6 0.4(3) . . . . ?
C5 N1 C4 C3 124.7(3) . . . . ?
C5 N1 C6 C7 -0.6(3) . . . . ?
C4 N1 C5 Ni1 2.4(5) . . . . ?
C4 N1 C5 N2 178.5(3) . . . . ?
C4 N1 C6 C7 -178.5(3) . . . . ?
C4 C3 C2 C1 70.0(3) . . . . ?
C6 N1 C5 Ni1 -175.3(3) . . . . ?
C6 N1 C5 N2 0.8(3) . . . . ?
C6 N1 C4 C3 -57.8(3) . . . . ?
C7 N2 C8 C13 -179.0(3) . . . . ?
C7 N2 C8 C9 -0.4(5) . . . . ?
C7 N2 C5 Ni1 176.69(19) . . . . ?
C7 N2 C5 N1 -0.7(3) . . . . ?
C15 N3 C12 C13 175.9(3) . . . . ?
C15 N3 C12 C11 -1.0(5) . . . . ?
C15 N3 C14 Ni1 -176.59(18) . . . . ?
C15 N3 C14 N4 1.5(3) . . . . ?
C16 N4 C17 C18A -93.4(3) . . . . ?
C16 N4 C17 C18B -64.1(9) . . . . ?
C16 N4 C14 Ni1 175.9(3) . . . . ?
C16 N4 C14 N3 -1.2(3) . . . . ?
C17 N4 C16 C15 177.9(2) . . . . ?
C17 N4 C14 Ni1 -1.3(5) . . . . ?
C17 N4 C14 N3 -178.4(2) . . . . ?
C17 C18A C19A C20A 173.1(3) . . . . ?
C17 C18B C19B C20B -175.0(16) . . . . ?
C14 Ni1 C13 C12 0.3(2) . . . . ?
C14 Ni1 C13 C8 175.4(2) . . . . ?
C14 N3 C12 C13 0.2(3) . . . . ?
C14 N3 C12 C11 -176.8(3) . . . . ?
C14 N3 C15 C16 -1.2(3) . . . . ?
C14 N4 C16 C15 0.5(3) . . . . ?
C14 N4 C17 C18A 83.5(3) . . . . ?
C14 N4 C17 C18B 112.8(9) . . . . ?

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

_exptl_crystal_recrystallization_method 'Vapour deposition'
