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

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

data_ac353
_database_code_depnum_ccdc_archive 'CCDC 1504344'
_audit_update_record             
;
2016-09-14 deposited with the CCDC.
2017-03-23 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT230_ac353               
;
PROBLEM: Hirshfeld Test Diff for    C2     --  C3      ..        7.3 s.u.
RESPONSE: The cyclopentadienyl ligand has common rotational disorder around a special position, modeling this disorder did not result in a significantly better fit
;
# Added during the CSD deposition process: Wednesday 14 September 2016 01:32 PM
# end Validation Reply Form

_audit_creation_date             2016-02-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_chemical_formula_moiety         'B F4, C21 H21 N2 Ni'
_chemical_formula_sum            'C21 H21 B F4 N2 Ni'
_chemical_formula_weight         446.93
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
Ni 0.35663 1.12491 12.83760 7.29200 4.44380 2.38000 3.87850 0.25650 12.17630
66.34210 1.03410005569
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z+1/2
3 -x,y+1/2,-z
4 -x+1/2,-y,z+1/2
5 -x,-y,-z
6 -x-1/2,y-1/2,z-1/2
7 x,-y-1/2,z
8 x-1/2,y,-z-1/2

_symmetry_Int_Tables_number      62
_cell_length_a                   11.9844(8)
_cell_length_b                   15.3276(11)
_cell_length_c                   10.8448(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1992.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    1756
_cell_measurement_theta_min      0.642
_cell_measurement_theta_max      0.745
_exptl_absorpt_coefficient_mu    1.019
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing 1995'
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.4900
_exptl_crystal_description       needle
_exptl_crystal_F_000             921.8941
_exptl_crystal_preparation       none
_exptl_crystal_recrystallization_method 'slow evaporation of CH2Cl2 solution'
_exptl_crystal_size_max          0.594
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.167
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            24840
_diffrn_reflns_theta_full        26.4699
_diffrn_reflns_theta_max         26.47
_diffrn_reflns_theta_min         2.30
_diffrn_ambient_temperature      100.02
_diffrn_measured_fraction_theta_full 0.9963
_diffrn_measured_fraction_theta_max 0.9963
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_special_details          none
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              0
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                1756
_reflns_number_total             2133
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.6944
_refine_diff_density_min         -0.5992
_refine_diff_density_rms         0.0775
_refine_ls_d_res_high            0.7973
_refine_ls_d_res_low             8.8530
_refine_ls_goodness_of_fit_ref   1.0667
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2133
_refine_ls_number_restraints     90
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0311
_refine_ls_restrained_S_all      1.0434
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1290
_refine_special_details          none
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C2) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C3) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq: with sigma of
0.1 and sigma for terminal atoms of 0.2
Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq: with sigma of
0.1 and sigma for terminal atoms of 0.2
Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.01
3.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C3(H3)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C8(H8), C11(H11), C10(H10)
3.c Idealised Me refined as rotating group:
 C5(H5a,H5b,H5c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_group
F1 F 0.45865(19) 0.25 0.34304(19) 0.0429(5) Uani 1.000000 2 S T P .
F2 F 0.50861(10) 0.17561(9) 0.51423(14) 0.0332(4) Uani 1.000000 1 . . . .
F3 F 0.64090(15) 0.25 0.4070(2) 0.0425(5) Uani 1.000000 2 S T P .
N1 N 0.17854(13) 0.66938(11) 0.36867(16) 0.0201(4) Uani 1.000000 1 . . . .
C6 C 0.19223(16) 0.57676(12) 0.35223(19) 0.0218(5) Uani 1.000000 1 . . . .
C4 C 0.12377(15) 0.70222(13) 0.46198(19) 0.0207(4) Uani 1.000000 1 . . . .
C7 C 0.12240(19) 0.53183(15) 0.2730(2) 0.0323(6) Uani 1.000000 1 . . . .
H7 H 0.06220(19) 0.56111(15) 0.2338(2) 0.0387(7) Uiso 1.000000 1 R . . .
C5 C 0.06551(17) 0.65105(14) 0.5589(2) 0.0274(5) Uani 1.000000 1 . . . .
H5a H 0.0949(9) 0.6672(7) 0.6401(2) 0.0410(7) Uiso 1.000000 1 GR . . .
H5b H -0.0146(2) 0.6635(8) 0.5558(10) 0.0410(7) Uiso 1.000000 1 GR . . .
H5c H 0.0779(11) 0.58864(14) 0.5448(8) 0.0410(7) Uiso 1.000000 1 GR . . .
C9 C 0.2301(2) 0.40234(17) 0.3048(3) 0.0365(6) Uani 1.000000 1 . . . .
H9 H 0.2434(2) 0.34226(17) 0.2890(3) 0.0438(7) Uiso 1.000000 1 R . . .
C8 C 0.1407(2) 0.44361(16) 0.2509(2) 0.0352(6) Uani 1.000000 1 . . . .
H8 H 0.0916(2) 0.41195(16) 0.1987(2) 0.0422(7) Uiso 1.000000 1 R . . .
C11 C 0.2822(2) 0.53563(15) 0.4066(3) 0.0368(6) Uani 1.000000 1 . . . .
H11 H 0.3306(2) 0.56672(15) 0.4603(3) 0.0442(7) Uiso 1.000000 1 R . . .
C10 C 0.3004(2) 0.44785(16) 0.3814(3) 0.0445(7) Uani 1.000000 1 . . . .
H10 H 0.3623(2) 0.41894(16) 0.4177(3) 0.0534(8) Uiso 1.000000 1 R . . .
B1 B 0.5298(3) 0.25 0.4445(3) 0.0247(7) Uani 1.000000 2 S T P .
Ni1 Ni 0.24599(2) 0.75 0.26523(4) 0.01781(18) Uani 1.000000 2 S T P .
C1 C 0.2658(3) 0.75 0.0709(4) 0.0402(9) Uani 1.000000 2 S TU P 1
H1 H 0.2065(3) 0.75 0.0060(4) 0.0482(11) Uiso 1.000000 2 RS T P 1
C2 C 0.3173(3) 0.67762(17) 0.1281(3) 0.0562(9) Uani 1.000000 1 . U . 1
H2 H 0.3006(3) 0.61498(17) 0.1100(3) 0.0675(10) Uiso 1.000000 1 R . . 1
C3 C 0.4003(2) 0.7075(3) 0.2069(3) 0.0744(12) Uani 1.000000 1 . U . 1
H3 H 0.4521(2) 0.6698(3) 0.2555(3) 0.0892(14) Uiso 1.000000 1 R . . 1


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
F1 B1 1.392(4) . ?
F2 B1 1.392(3) 7_565 ?
F3 B1 1.392(4) . ?
N1 C6 1.440(3) . ?
N1 C4 1.307(3) . ?
N1 Ni1 1.8544(16) 7_575 ?
C6 C7 1.383(3) . ?
C6 C11 1.381(3) . ?
C4 C4 1.465(4) 7_575 ?
C4 C5 1.486(3) . ?
C7 C8 1.391(3) . ?
C9 C8 1.375(4) . ?
C9 C10 1.374(4) . ?
C11 C10 1.390(4) . ?
Ni1 C1 2.121(4) . ?
Ni1 C2 2.043(2) 7_575 ?
Ni1 C2 2.043(2) . ?
Ni1 C3 2.060(3) . ?
Ni1 C3 2.060(3) 7_575 ?
C1 C2 1.413(4) 7_575 ?
C1 C2 1.413(4) . ?
C2 C3 1.389(5) . ?
C3 C3 1.302(8) 7_575 ?

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
C4 N1 C6 122.18(17) . . ?
Ni1 N1 C6 122.16(13) 7_575 . ?
Ni1 N1 C4 115.51(14) 7_575 . ?
C7 C6 N1 119.92(18) . . ?
C11 C6 N1 119.08(19) . . ?
C11 C6 C7 120.7(2) . . ?
C4 C4 N1 112.65(12) 7_575 . ?
C5 C4 N1 125.49(18) . . ?
C8 C7 C6 119.7(2) . . ?
C10 C9 C8 120.1(2) . . ?
C9 C8 C7 119.8(2) . . ?
C10 C11 C6 118.7(2) . . ?
C11 C10 C9 120.9(2) . . ?
F2 B1 F1 108.52(18) . . ?
F2 B1 F1 108.52(18) 7_565 . ?
F2 B1 F2 110.0(3) 7_565 . ?
F3 B1 F1 110.8(3) . . ?
F3 B1 F2 109.47(17) . . ?
F3 B1 F2 109.47(17) . 7_565 ?
N1 Ni1 N1 83.57(10) . 7_575 ?
C2 Ni1 C1 39.62(10) . . ?
C2 Ni1 C1 39.62(10) 7_575 . ?
C2 Ni1 C2 65.79(15) . 7_575 ?
C3 Ni1 C1 66.05(12) 7_575 . ?
C3 Ni1 C1 66.05(12) . . ?
C3 Ni1 C2 39.56(14) . . ?
C3 Ni1 C2 64.69(13) . 7_575 ?
C3 Ni1 C2 64.69(13) 7_575 . ?
C3 Ni1 C2 39.56(14) 7_575 7_575 ?
C3 Ni1 C3 36.9(2) . 7_575 ?
C2 C1 C2 103.5(4) . 7_575 ?
C3 C2 C1 108.9(3) . 7_575 ?
C3 C3 C2 109.27(18) 7_575 . ?

_olex2_exptl_crystal_mounting_method 
'crystals were mounted using perfluoropolyalkylether from ABCR viscosity 1800 cts on to a cryoloop'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_U_iso_atom_site_label
_restr_U_iso_weight_param
C1 0.1000
C1 0.0100
C1 0.1000
C1 0.1000
C1 0.0100
C2 0.1000
C2 0.1000
C2 0.0100
C2 0.1000
C2 0.0100
C3 0.1000
C3 0.0100
C3 0.1000
C3 0.1000
C3 0.0100

####################################################################### 
# 
# 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_ac354
_database_code_depnum_ccdc_archive 'CCDC 1504345'
_audit_update_record             
;
2016-09-14 deposited with the CCDC.
2017-03-23 downloaded from the CCDC.
;
_audit_creation_date             2016-01-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_chemical_formula_moiety         'C23 H25 N2 Ni O2, B F4'
_chemical_formula_sum            'C23 H25 B F4 N2 Ni O2'
_chemical_formula_weight         506.47
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
Ni 0.35663 1.12491 12.83760 7.29200 4.44380 2.38000 3.87850 0.25650 12.17630
66.34210 1.03410005569
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 x,-y,z+1/2
3 x+1/2,y+1/2,z
4 x+1/2,-y+1/2,z+1/2

_symmetry_Int_Tables_number      9
_cell_length_a                   9.1415(8)
_cell_length_b                   21.906(2)
_cell_length_c                   11.8206(10)
_cell_angle_alpha                90
_cell_angle_beta                 104.863(4)
_cell_angle_gamma                90
_cell_volume                     2287.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    3969
_cell_measurement_theta_max      26.440
_cell_measurement_theta_min      2.1100
_exptl_absorpt_coefficient_mu    0.903
_exptl_absorpt_correction_T_max  0.9962
_exptl_absorpt_correction_T_min  0.9005
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'de Meulenaar 1965'
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.4702
_exptl_crystal_description       prism
_exptl_crystal_F_000             1048.7802
_exptl_crystal_preparation       n/a
_exptl_crystal_recrystallization_method 
'by slow evaporation of a concentrated CH2Cl2 solution'
_exptl_crystal_size_max          0.322
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.105
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15856
_diffrn_reflns_theta_full        26.4425
_diffrn_reflns_theta_max         26.44
_diffrn_reflns_theta_min         1.86
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.9662
_diffrn_measured_fraction_theta_max 0.9662
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.941
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              27
_reflns_limit_k_min              -27
_reflns_limit_l_max              14
_reflns_limit_l_min              -14
_reflns_number_gt                3969
_reflns_number_total             4550
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.5502
_refine_diff_density_min         -0.4182
_refine_diff_density_rms         0.0805
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   8.539(15)
_refine_ls_d_res_high            0.7980
_refine_ls_d_res_low             10.9528
_refine_ls_goodness_of_fit_ref   1.0362
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    61
_refine_ls_number_parameters     334
_refine_ls_number_reflns         4550
_refine_ls_number_restraints     108
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0552
_refine_ls_restrained_S_all      1.0232
_refine_ls_shift/su_max          0.0035
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0780P)²+9.5400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1373
_refine_ls_wR_factor_ref         0.1453
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C10) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C13)
\\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C11) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C17b) \\sim Ueq, Uanis(C18b) \\sim Ueq, Uanis(C19b) \\sim Ueq,
Uanis(C20b) \\sim Ueq, Uanis(C21b) \\sim Ueq, Uanis(C22b) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(N2b) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(N2a) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(N2b) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O2b) \\sim Ueq, Uanis(C24) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
: with sigma of 0.02 and sigma for terminal atoms of 0.04
: with sigma of 0.01 and sigma for terminal atoms of 0.02
: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C24a) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(N2a) = Uanis(N2b)
3. Others
 Sof(O2b)=Sof(N2b)=Sof(C17b)=Sof(C18b)=Sof(C19b)=Sof(H19b)=Sof(C20b)=Sof(H20b)=
 Sof(C21b)=Sof(H21b)=Sof(C22b)=Sof(C24)=Sof(H24a)=Sof(H24b)=Sof(H24c)=Sof(H18b)=
 1-FVAR(1)
 Sof(O2a)=Sof(N2a)=Sof(C17a)=Sof(C22a)=Sof(C21a)=Sof(H21a)=Sof(C20a)=Sof(H20a)=
 Sof(C19a)=Sof(H19a)=Sof(C18a)=Sof(H18a)=FVAR(1)
 Sof(C0ab)=1-FVAR(2)
 Sof(C24a)=Sof(H24d)=Sof(H24e)=Sof(H24f)=FVAR(2)
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C14(H14), C13(H13), C12(H12),
 C11(H11), C21a(H21a), C20a(H20a), C19a(H19a), C18a(H18a), C19b(H19b),
 C20b(H20b), C21b(H21b), C18b(H18b)
4.b Fitted pentagon refined as free rotating group:
 C1(C2,C3,C4,C5)
4.c Fitted hexagon refined as free rotating group:
 C10(C15,C14,C13,C12,C11), C17a(C22a,C21a,C20a,C19a,C18a), C17b(C18b,C19b,C20b,
 C21b,C22b)
4.d Idealised Me refined as rotating group:
 C6(H6a,H6b,H6c), C9(H9a,H9b,H9c), C16(H16a,H16b,H16c), C24(H24c,H24b,H24a),
 C24a(H24d,H24e,H24f)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_disorder_group
Ni1 Ni -0.16076(8) -0.37755(2) -0.53770(7) 0.01996(16) Uani 1.000000 . . .
F1 F -0.4395(5) -0.6397(2) -0.6605(3) 0.0706(15) Uani 1.000000 . . .
F2 F -0.2732(5) -0.6314(2) -0.4826(4) 0.092(2) Uani 1.000000 . . .
F3 F -0.4010(5) -0.54916(17) -0.5701(3) 0.0559(11) Uani 1.000000 . . .
F4 F -0.5149(6) -0.6198(3) -0.4967(5) 0.108(3) Uani 1.000000 . . .
O1 O -0.5059(4) -0.29664(18) -0.4387(3) 0.0291(9) Uani 1.000000 . . .
N1 N -0.3664(5) -0.37964(18) -0.5429(4) 0.0173(9) Uani 1.000000 . . .
C1 C 0.0114(3) -0.38856(13) -0.6251(3) 0.0311(13) Uani 1.000000 . . .
H1 H 0.0511(3) -0.42656(13) -0.6422(3) 0.0373(15) Uiso 1.000000 R . .
C2 C 0.0664(4) -0.35334(16) -0.5221(2) 0.0319(14) Uani 1.000000 G . .
H2 H 0.1493(4) -0.36362(16) -0.4582(2) 0.0383(17) Uiso 1.000000 R . .
C3 C -0.0243(5) -0.30003(15) -0.5315(3) 0.0356(14) Uani 1.000000 G . .
H3 H -0.0127(5) -0.26840(15) -0.4749(3) 0.0427(17) Uiso 1.000000 R . .
C4 C -0.1354(4) -0.30232(15) -0.6402(4) 0.0374(15) Uani 1.000000 G . .
H4 H -0.2111(4) -0.27248(15) -0.6692(4) 0.0449(18) Uiso 1.000000 R . .
C5 C -0.1133(3) -0.35703(17) -0.6981(2) 0.0354(14) Uani 1.000000 G . .
H5 H -0.1717(3) -0.37023(17) -0.7726(2) 0.0425(17) Uiso 1.000000 R . .
C6 C -0.2907(6) -0.4947(2) -0.3049(5) 0.0266(11) Uani 1.000000 . . .
H6a H -0.342(4) -0.4743(6) -0.252(2) 0.0399(17) Uiso 1.000000 GR . .
H6b H -0.351(4) -0.5298(9) -0.3413(5) 0.0399(17) Uiso 1.000000 GR . .
H6c H -0.1905(6) -0.5087(14) -0.261(2) 0.0399(17) Uiso 1.000000 GR . .
C7 C -0.2738(6) -0.4512(2) -0.3974(4) 0.0212(10) Uani 1.000000 . . .
C8 C -0.4035(5) -0.4180(2) -0.4688(4) 0.0191(10) Uani 1.000000 . . .
C9 C -0.5584(6) -0.4292(2) -0.4561(4) 0.0242(11) Uani 1.000000 . . .
H9a H -0.5673(14) -0.4126(15) -0.3811(15) 0.0363(16) Uiso 1.000000 GR . .
H9b H -0.6322(6) -0.4091(15) -0.5203(19) 0.0363(16) Uiso 1.000000 GR . .
H9c H -0.5782(16) -0.4732(3) -0.459(3) 0.0363(16) Uiso 1.000000 GR . .
C10 C -0.4785(2) -0.33962(12) -0.6123(2) 0.0182(10) Uani 1.000000 . U .
C15 C -0.5464(3) -0.29559(14) -0.55806(18) 0.0235(11) Uani 1.000000 G U .
C14 C -0.6478(3) -0.25424(13) -0.6252(3) 0.0272(11) Uani 1.000000 G U .
H14 H -0.6942(3) -0.22415(13) -0.5881(3) 0.0326(14) Uiso 1.000000 R . .
C13 C -0.6812(3) -0.25692(13) -0.7466(3) 0.0315(13) Uani 1.000000 G U .
H13 H -0.7505(3) -0.22865(13) -0.7925(3) 0.0378(15) Uiso 1.000000 R . .
C12 C -0.6133(4) -0.30095(15) -0.80092(18) 0.0305(12) Uani 1.000000 G U .
H12 H -0.6361(4) -0.30278(15) -0.88391(18) 0.0366(15) Uiso 1.000000 R . .
C11 C -0.5119(3) -0.34230(13) -0.7338(2) 0.0231(11) Uani 1.000000 G U .
H11 H -0.4655(3) -0.37239(13) -0.7709(2) 0.0278(13) Uiso 1.000000 R . .
C16 C -0.5705(7) -0.2524(3) -0.3774(5) 0.0382(15) Uani 1.000000 . . .
H16a H -0.6811(7) -0.2542(15) -0.404(3) 0.057(2) Uiso 1.000000 GR . .
H16b H -0.539(4) -0.2609(13) -0.2932(6) 0.057(2) Uiso 1.000000 GR . .
H16c H -0.536(4) -0.2115(4) -0.392(3) 0.057(2) Uiso 1.000000 GR . .
B1 B -0.4047(9) -0.6113(3) -0.5540(6) 0.0365(16) Uani 1.000000 . . .
O2a O 0.0451(5) -0.3837(2) -0.2472(4) 0.0386(15) Uani 0.824(9) . . 1
N2a N -0.1478(6) -0.4396(3) -0.4256(5) 0.0189(15) Uani 0.824(9) . U 1
C17a C -0.0099(3) -0.46854(19) -0.3679(3) 0.0205(14) Uani 0.824(9) . . 1
C22a C 0.0917(4) -0.43857(16) -0.2771(3) 0.0259(15) Uani 0.824(9) G . 1
C21a C 0.2310(3) -0.46492(19) -0.2252(3) 0.0288(16) Uani 0.824(9) G . 1
H21a H 0.3004(3) -0.44444(19) -0.1631(3) 0.035(2) Uiso 0.824(9) R . 1
C20a C 0.2688(3) -0.52123(19) -0.2639(3) 0.0251(15) Uani 0.824(9) G . 1
H20a H 0.3641(3) -0.53924(19) -0.2284(3) 0.0301(18) Uiso 0.824(9) R . 1
C19a C 0.1673(4) -0.55120(17) -0.3546(4) 0.0299(16) Uani 0.824(9) G . 1
H19a H 0.1931(4) -0.58968(17) -0.3811(4) 0.036(2) Uiso 0.824(9) R . 1
C18a C 0.0279(4) -0.52485(19) -0.4066(3) 0.0264(15) Uani 0.824(9) G . 1
H18a H -0.0415(4) -0.54533(19) -0.4686(3) 0.0317(19) Uiso 0.824(9) R . 1
O2b O -0.0370(11) -0.5322(10) -0.4689(11) 0.030(6) Uani 0.176(9) . U 2
N2b N -0.1443(16) -0.425(2) -0.4118(15) 0.0189(15) Uani 0.176(9) . U 2
C17b C -0.0034(4) -0.4505(9) -0.3399(4) 0.027(10) Uani 0.176(9) . U 2
C18b C 0.0816(7) -0.4187(9) -0.2436(6) 0.031(9) Uani 0.176(9) G U 2
C19b C 0.2236(6) -0.4400(10) -0.1839(6) 0.032(8) Uani 0.176(9) G U 2
H19b H 0.2817(6) -0.4183(10) -0.1181(6) 0.038(10) Uiso 0.176(9) R . 2
C20b C 0.2806(8) -0.4932(10) -0.2205(8) 0.027(8) Uani 0.176(9) G U 2
H20b H 0.3777(8) -0.5078(10) -0.1798(8) 0.032(10) Uiso 0.176(9) R . 2
C21b C 0.1956(12) -0.5250(9) -0.3168(11) 0.028(8) Uani 0.176(9) G U 2
H21b H 0.2346(12) -0.5614(9) -0.3419(11) 0.033(9) Uiso 0.176(9) R . 2
C22b C 0.0536(9) -0.5037(9) -0.3765(8) 0.028(9) Uani 0.176(9) G U 2
C24 C 0.0118(18) -0.5867(17) -0.5088(17) 0.041(9) Uani 0.176(9) . U 2
H24a H 0.05(3) -0.579(3) -0.578(14) 0.061(14) Uiso 0.176(9) GR . 2
H24b H 0.09(2) -0.604(7) -0.447(9) 0.061(14) Uiso 0.176(9) GR . 2
H24c H -0.073(8) -0.616(5) -0.53(2) 0.061(14) Uiso 0.176(9) GR . 2
C24a C 0.1498(10) -0.3504(5) -0.1590(8) 0.060(4) Uani 0.79(3) . U 1
H18b H 0.0426(7) -0.3823(9) -0.2186(6) 0.038(11) Uiso 0.176(9) R . 2
H24d H 0.221(5) -0.329(3) -0.1941(14) 0.090(6) Uiso 0.79(3) GR . 1
H24e H 0.0949(12) -0.321(3) -0.123(5) 0.090(6) Uiso 0.79(3) GR . 1
H24f H 0.206(6) -0.3786(6) -0.099(4) 0.090(6) Uiso 0.79(3) GR . 1


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 1.866(4) . ?
Ni1 C1 2.107(3) . ?
Ni1 C2 2.105(3) . ?
Ni1 C3 2.097(4) . ?
Ni1 C4 2.094(3) . ?
Ni1 C5 2.100(3) . ?
Ni1 N2a 1.881(6) . ?
Ni1 N2b 1.79(3) . ?
F1 B1 1.366(8) . ?
F2 B1 1.353(8) . ?
F3 B1 1.377(8) . ?
F4 B1 1.363(9) . ?
O1 C15 1.364(4) . ?
O1 C16 1.427(6) . ?
N1 C8 1.319(6) . ?
N1 C10 1.435(4) . ?
C1 C2 1.4200 . ?
C1 C5 1.4200 . ?
C2 C3 1.4200 . ?
C3 C4 1.4200 . ?
C4 C5 1.4200 . ?
C6 C7 1.488(7) . ?
C7 C8 1.461(7) . ?
C7 N2a 1.304(7) . ?
C7 N2b 1.36(2) . ?
C8 C9 1.482(7) . ?
C10 C15 1.3900 . ?
C10 C11 1.3900 . ?
C15 C14 1.3900 . ?
C14 C13 1.3900 . ?
C13 C12 1.3900 . ?
C12 C11 1.3900 . ?
O2a C22a 1.353(6) . ?
O2a C24a 1.423(10) . ?
N2a C17a 1.419(6) . ?
C17a C22a 1.3900 . ?
C17a C18a 1.3900 . ?
C22a C21a 1.3900 . ?
C21a C20a 1.3900 . ?
C20a C19a 1.3900 . ?
C19a C18a 1.3900 . ?
O2b C22b 1.343(18) . ?
O2b C24 1.40(4) . ?
N2b C17b 1.46(2) . ?
C17b C18b 1.3900 . ?
C17b C22b 1.3900 . ?
C18b C19b 1.3900 . ?
C19b C20b 1.3900 . ?
C20b C21b 1.3900 . ?
C21b C22b 1.3900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Ni1 N1 148.70(15) . . ?
C2 Ni1 N1 166.44(16) . . ?
C2 Ni1 C1 39.40(5) . . ?
C3 Ni1 N1 127.32(16) . . ?
C3 Ni1 C1 66.26(8) . . ?
C3 Ni1 C2 39.50(6) . . ?
C4 Ni1 N1 105.11(16) . . ?
C4 Ni1 C1 66.32(7) . . ?
C4 Ni1 C2 66.35(8) . . ?
C4 Ni1 C3 39.61(6) . . ?
C5 Ni1 N1 114.56(15) . . ?
C5 Ni1 C1 39.46(5) . . ?
C5 Ni1 C2 66.24(7) . . ?
C5 Ni1 C3 66.39(8) . . ?
C5 Ni1 C4 39.59(6) . . ?
C16 O1 C15 118.5(4) . . ?
C8 N1 Ni1 115.0(3) . . ?
C10 N1 Ni1 124.7(3) . . ?
C10 N1 C8 120.1(4) . . ?
C2 C1 Ni1 70.2 . . ?
C5 C1 Ni1 70.0 . . ?
C5 C1 C2 108.0 . . ?
C1 C2 Ni1 70.36(13) . . ?
C3 C2 Ni1 69.94(12) . . ?
C3 C2 C1 108.0 . . ?
C2 C3 Ni1 70.56(11) . . ?
C4 C3 Ni1 70.06(14) . . ?
C4 C3 C2 108.0 . . ?
C3 C4 Ni1 70.33(14) . . ?
C5 C4 Ni1 70.43(12) . . ?
C5 C4 C3 108.0 . . ?
C1 C5 Ni1 70.54(12) . . ?
C4 C5 Ni1 69.98(12) . . ?
C4 C5 C1 108.0 . . ?
C8 C7 C6 121.4(4) . . ?
C7 C8 N1 113.1(4) . . ?
C9 C8 N1 126.0(4) . . ?
C9 C8 C7 121.0(4) . . ?
C15 C10 N1 119.8 . . ?
C11 C10 N1 120.0 . . ?
C11 C10 C15 120.0 . . ?
C10 C15 O1 115.5(2) . . ?
C14 C15 O1 124.5(2) . . ?
C14 C15 C10 120.0 . . ?
C13 C14 C15 120.0 . . ?
C12 C13 C14 120.0 . . ?
C11 C12 C13 120.0 . . ?
C12 C11 C10 120.0 . . ?
F2 B1 F1 112.8(6) . . ?
F3 B1 F1 109.3(5) . . ?
F3 B1 F2 110.9(6) . . ?
F4 B1 F1 111.7(6) . . ?
F4 B1 F2 107.4(6) . . ?
F4 B1 F3 104.5(6) . . ?
C24a O2a C22a 116.7(5) . . ?
C7 N2a Ni1 114.9(4) . . ?
C22a C17a N2a 119.6 . . ?
C18a C17a N2a 120.2 . . ?
C18a C17a C22a 120.0 . . ?
C17a C22a O2a 115.4(3) . . ?
C21a C22a O2a 124.6(3) . . ?
C21a C22a C17a 120.0 . . ?
C20a C21a C22a 120.0 . . ?
C19a C20a C21a 120.0 . . ?
C18a C19a C20a 120.0 . . ?
C19a C18a C17a 120.0 . . ?
C24 O2b C22b 119.2(13) . . ?
C7 N2b Ni1 117.2(11) . . ?
C18b C17b N2b 120.6 . . ?
C22b C17b N2b 119.0 . . ?
C22b C17b C18b 120.0 . . ?
C19b C18b C17b 120.0 . . ?
C20b C19b C18b 120.0 . . ?
C21b C20b C19b 120.000000000(18) . . ?
C22b C21b C20b 120.0 . . ?
C17b C22b O2b 116.1(12) . . ?
C21b C22b O2b 123.9(12) . . ?
C21b C22b C17b 120.0 . . ?

_olex2_exptl_crystal_mounting_method 
'crystals were mounted using perfluoropolyalkylether from ABCR viscosity 1800 cts on to a cryoloop'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_U_iso_atom_site_label
_restr_U_iso_weight_param
C10 0.0100
C15 0.0100
C14 0.0100
C13 0.0100
C12 0.0100
C11 0.0100
N2a 0.1000
O2b 0.0100
N2b 0.0100
N2b 0.0100
C17b 0.0100
C18b 0.0100
C19b 0.0100
C20b 0.0100
C21b 0.0100
C22b 0.0100
C24 0.0100
C24a 0.0100

####################################################################### 
# 
# 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_ac352
_database_code_depnum_ccdc_archive 'CCDC 1504346'
_audit_update_record             
;
2016-09-14 deposited with the CCDC.
2017-03-23 downloaded from the CCDC.
;
_audit_creation_date             2016-01-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22.99 H19 F5.96 N2 Ni, B F4'
_chemical_formula_sum            'C22.988 H19 B F9.965 N2 Ni'
_chemical_formula_weight         582.12
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
Ni 0.35663 1.12491 12.83760 7.29200 4.44380 2.38000 3.87850 0.25650 12.17630
66.34210 1.03410005569
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           ' P 2c -2ac'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,z+1/2
3 -x+1/2,y,z+1/2
4 x+1/2,-y,z

_symmetry_Int_Tables_number      29
_cell_length_a                   19.7420(17)
_cell_length_b                   7.5757(5)
_cell_length_c                   15.8268(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2367.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    3450
_cell_measurement_theta_min      2.335
_cell_measurement_theta_max      26.390
_exptl_absorpt_coefficient_mu    0.913
_exptl_absorpt_correction_T_max  0.8945
_exptl_absorpt_correction_T_min  0.7908
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(de Meulenaar et al., 1965)'
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.6333
_exptl_crystal_description       prism
_exptl_crystal_F_000             1176.7839
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'slow evaporation of CH2Cl2'
_exptl_crystal_size_max          0.209
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.116
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_av_unetI/netI     0.0946
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16211
_diffrn_reflns_theta_full        26.3876
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         2.06
_diffrn_ambient_temperature      99.99
_diffrn_measured_fraction_theta_full 0.9765
_diffrn_measured_fraction_theta_max 0.9765
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.952
_reflns_limit_h_max              24
_reflns_limit_h_min              -24
_reflns_limit_k_max              9
_reflns_limit_k_min              -9
_reflns_limit_l_max              17
_reflns_limit_l_min              -19
_reflns_number_gt                3450
_reflns_number_total             4737
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.7571
_refine_diff_density_min         -0.6971
_refine_diff_density_rms         0.1439
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.00(2)
_refine_ls_d_res_high            0.7996
_refine_ls_d_res_low             9.8710
_refine_ls_goodness_of_fit_ref   1.0121
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    35
_refine_ls_number_parameters     336
_refine_ls_number_reflns         4737
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.0097
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0309P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0885
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C23-C22 \\sim C23-F6 \\sim C23-F5 \\sim C23-F4
 with sigma of 0.02
 F4-F6 \\sim F6-F5 \\sim F4-F5
 with sigma of 0.02
 C23-C22 \\sim C23-F6 \\sim C23-F5 \\sim C23-F4
 with sigma of 0.02
 F4-F6 \\sim F6-F5 \\sim F4-F5
 with sigma of 0.02
 C23-C22 \\sim C23-F6 \\sim C23-F5 \\sim C23-F4
 with sigma of 0.02
 F4-F6 \\sim F6-F5 \\sim F4-F5
 with sigma of 0.02
3. Others
 Sof(C23)=Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13),
 C14(H14), C18(H18), C19(H19), C20(H20), C21(H21)
4.b Idealised Me refined as rotating group:
 C8(H8a,H8b,H8c), C9(H9a,H9b,H9c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
_atom_site_disorder_group
Ni1 Ni -0.47393(2) -0.40514(6) -0.33870(3) 0.01415(13) Uani 1.000000 . .
F1 F -0.58874(15) -0.0569(3) -0.3355(2) 0.0496(8) Uani 1.000000 . .
F2 F -0.66254(14) 0.0658(4) -0.2568(2) 0.0458(9) Uani 1.000000 . .
F3 F -0.55951(15) 0.0546(4) -0.2181(2) 0.0466(9) Uani 1.000000 . .
N1 N -0.39104(16) -0.3043(4) -0.3080(2) 0.0122(8) Uani 1.000000 . .
N2 N -0.50240(18) -0.3114(4) -0.2356(2) 0.0136(8) Uani 1.000000 . .
C1 C -0.4872(2) -0.4280(6) -0.4704(3) 0.0221(12) Uani 1.000000 . .
H1 H -0.4717(2) -0.3470(6) -0.5119(3) 0.0265(14) Uiso 1.000000 R .
C2 C -0.4492(2) -0.5735(6) -0.4361(3) 0.0227(11) Uani 1.000000 . .
H2 H -0.4034(2) -0.6008(6) -0.4491(3) 0.0272(14) Uiso 1.000000 R .
C3 C -0.4908(2) -0.6685(6) -0.3804(3) 0.0221(11) Uani 1.000000 . .
H3 H -0.4803(2) -0.7767(6) -0.3530(3) 0.0265(14) Uiso 1.000000 R .
C4 C -0.5519(2) -0.5699(6) -0.3734(3) 0.0199(11) Uani 1.000000 . .
H4 H -0.5880(2) -0.5952(6) -0.3356(3) 0.0239(13) Uiso 1.000000 R .
C5 C -0.5504(2) -0.4272(6) -0.4320(3) 0.0226(11) Uani 1.000000 . .
H5 H -0.5861(2) -0.3463(6) -0.4428(3) 0.0271(14) Uiso 1.000000 R .
C6 C -0.3888(2) -0.2367(5) -0.2325(3) 0.0116(10) Uani 1.000000 . .
C7 C -0.4546(2) -0.2398(5) -0.1888(3) 0.0130(10) Uani 1.000000 . .
C8 C -0.3270(2) -0.1682(5) -0.1904(3) 0.0172(11) Uani 1.000000 . .
H8a H -0.3128(8) -0.2508(18) -0.1461(11) 0.0259(16) Uiso 1.000000 GR .
H8b H -0.2906(4) -0.156(3) -0.2321(4) 0.0259(16) Uiso 1.000000 GR .
H8c H -0.3368(4) -0.0529(16) -0.1651(14) 0.0259(16) Uiso 1.000000 GR .
C9 C -0.4640(2) -0.1751(6) -0.1016(3) 0.0188(11) Uani 1.000000 . .
H9a H -0.5124(2) -0.173(3) -0.0880(6) 0.0281(16) Uiso 1.000000 GR .
H9b H -0.4404(11) -0.254(2) -0.0622(3) 0.0281(16) Uiso 1.000000 GR .
H9c H -0.4455(12) -0.0556(14) -0.0967(5) 0.0281(16) Uiso 1.000000 GR .
C10 C -0.5694(2) -0.3366(6) -0.2025(3) 0.0139(10) Uani 1.000000 . .
C11 C -0.5832(2) -0.4972(6) -0.1639(3) 0.0181(11) Uani 1.000000 . .
H11 H -0.5485(2) -0.5834(6) -0.1586(3) 0.0217(13) Uiso 1.000000 R .
C12 C -0.6472(2) -0.5311(6) -0.1335(3) 0.0195(11) Uani 1.000000 . .
H12 H -0.6559(2) -0.6405(6) -0.1063(3) 0.0234(13) Uiso 1.000000 R .
C13 C -0.6992(2) -0.4101(6) -0.1416(3) 0.0236(11) Uani 1.000000 . .
H13 H -0.7432(2) -0.4353(6) -0.1205(3) 0.0283(13) Uiso 1.000000 R .
C14 C -0.6854(2) -0.2500(6) -0.1815(3) 0.0216(11) Uani 1.000000 . .
H14 H -0.7206(2) -0.1655(6) -0.1877(3) 0.0259(14) Uiso 1.000000 R .
C15 C -0.6213(2) -0.2117(6) -0.2123(3) 0.0165(10) Uani 1.000000 . .
C16 C -0.6076(2) -0.0386(6) -0.2551(3) 0.0233(12) Uani 1.000000 . .
C17 C -0.3304(2) -0.3199(5) -0.3572(3) 0.0166(11) Uani 1.000000 . .
C18 C -0.2930(2) -0.4736(5) -0.3507(3) 0.0197(11) Uani 1.000000 . .
H18 H -0.3064(2) -0.5628(5) -0.3120(3) 0.0236(13) Uiso 1.000000 R .
C19 C -0.2358(2) -0.4980(6) -0.4005(3) 0.0222(11) Uani 1.000000 . .
H19 H -0.2107(2) -0.6046(6) -0.3964(3) 0.0266(13) Uiso 1.000000 R .
C20 C -0.2151(2) -0.3662(6) -0.4567(3) 0.0238(12) Uani 1.000000 . .
H20 H -0.1759(2) -0.3824(6) -0.4906(3) 0.0286(14) Uiso 1.000000 R .
C21 C -0.2516(2) -0.2153(6) -0.4623(3) 0.0212(11) Uani 1.000000 . .
H21 H -0.2370(2) -0.1260(6) -0.5003(3) 0.0254(13) Uiso 1.000000 R .
C22 C -0.3102(2) -0.1860(6) -0.4139(3) 0.0178(11) Uani 1.000000 D .
C23 C -0.3490(2) -0.0226(6) -0.4253(3) 0.0220(12) Uani 0.988(5) D 1
F4 F -0.41112(16) -0.0457(4) -0.4558(2) 0.0569(12) Uani 0.988(5) D 1
F5 F -0.32033(16) 0.0930(4) -0.4771(2) 0.0595(12) Uani 0.988(5) D 1
F6 F -0.35822(17) 0.0674(4) -0.35377(17) 0.0510(11) Uani 0.988(5) D 1
F7 F -0.55084(12) -0.2502(3) -0.63730(17) 0.0307(7) Uani 1.000000 . .
F8 F -0.62422(13) -0.4754(3) -0.61338(17) 0.0250(6) Uani 1.000000 . .
F9 F -0.64822(13) -0.1995(3) -0.56494(16) 0.0288(7) Uani 1.000000 . .
F10 F -0.65168(14) -0.2560(3) -0.70531(16) 0.0280(7) Uani 1.000000 . .
B1 B -0.6184(3) -0.2944(7) -0.6304(3) 0.0177(12) Uani 1.000000 . .


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 1.870(3) . ?
Ni1 N2 1.867(3) . ?
Ni1 C1 2.108(4) . ?
Ni1 C2 2.060(4) . ?
Ni1 C3 2.128(4) . ?
Ni1 C4 2.057(4) . ?
Ni1 C5 2.118(5) . ?
F1 C16 1.333(6) . ?
F2 C16 1.343(5) . ?
F3 C16 1.320(5) . ?
N1 C6 1.301(5) . ?
N1 C17 1.432(5) . ?
N2 C7 1.317(5) . ?
N2 C10 1.435(5) . ?
C1 C2 1.439(6) . ?
C1 C5 1.388(6) . ?
C2 C3 1.404(6) . ?
C3 C4 1.424(6) . ?
C4 C5 1.424(6) . ?
C6 C7 1.472(6) . ?
C6 C8 1.484(5) . ?
C7 C9 1.475(6) . ?
C10 C11 1.387(6) . ?
C10 C15 1.404(6) . ?
C11 C12 1.377(6) . ?
C12 C13 1.382(6) . ?
C13 C14 1.395(6) . ?
C14 C15 1.385(6) . ?
C15 C16 1.501(6) . ?
C17 C18 1.384(5) . ?
C17 C22 1.412(6) . ?
C18 C19 1.389(6) . ?
C19 C20 1.398(6) . ?
C20 C21 1.354(6) . ?
C21 C22 1.404(6) . ?
C22 C23 1.467(6) . ?
C23 F4 1.329(5) . ?
C23 F5 1.328(5) . ?
C23 F6 1.334(5) . ?
F7 B1 1.380(6) . ?
F8 B1 1.402(6) . ?
F9 B1 1.391(6) . ?
F10 B1 1.386(6) . ?

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 Ni1 N1 83.18(15) . . ?
C1 Ni1 N1 113.50(16) . . ?
C1 Ni1 N2 149.17(17) . . ?
C2 Ni1 N1 103.85(17) . . ?
C2 Ni1 N2 164.05(16) . . ?
C2 Ni1 C1 40.38(17) . . ?
C3 Ni1 N1 126.90(16) . . ?
C3 Ni1 N2 125.52(16) . . ?
C3 Ni1 C1 66.20(17) . . ?
C3 Ni1 C2 39.12(17) . . ?
C4 Ni1 N1 166.49(16) . . ?
C4 Ni1 N2 103.82(16) . . ?
C4 Ni1 C1 66.00(17) . . ?
C4 Ni1 C2 66.56(18) . . ?
C4 Ni1 C3 39.74(17) . . ?
C5 Ni1 N1 146.80(16) . . ?
C5 Ni1 N2 115.16(17) . . ?
C5 Ni1 C1 38.35(17) . . ?
C5 Ni1 C2 66.32(18) . . ?
C5 Ni1 C3 66.29(17) . . ?
C5 Ni1 C4 39.86(16) . . ?
C6 N1 Ni1 115.4(3) . . ?
C17 N1 Ni1 123.8(3) . . ?
C17 N1 C6 120.2(3) . . ?
C7 N2 Ni1 115.6(3) . . ?
C10 N2 Ni1 123.1(3) . . ?
C10 N2 C7 120.7(4) . . ?
C2 C1 Ni1 68.0(2) . . ?
C5 C1 Ni1 71.2(3) . . ?
C5 C1 C2 107.9(4) . . ?
C1 C2 Ni1 71.6(3) . . ?
C3 C2 Ni1 73.1(3) . . ?
C3 C2 C1 108.9(4) . . ?
C2 C3 Ni1 67.8(2) . . ?
C4 C3 Ni1 67.4(2) . . ?
C4 C3 C2 106.0(4) . . ?
C3 C4 Ni1 72.8(3) . . ?
C5 C4 Ni1 72.4(3) . . ?
C5 C4 C3 109.2(4) . . ?
C1 C5 Ni1 70.4(3) . . ?
C4 C5 Ni1 67.8(3) . . ?
C4 C5 C1 107.5(4) . . ?
C7 C6 N1 113.3(4) . . ?
C8 C6 N1 125.3(4) . . ?
C8 C6 C7 121.3(4) . . ?
C6 C7 N2 112.0(4) . . ?
C9 C7 N2 124.9(4) . . ?
C9 C7 C6 123.1(4) . . ?
C11 C10 N2 117.2(4) . . ?
C15 C10 N2 122.9(4) . . ?
C15 C10 C11 119.7(4) . . ?
C12 C11 C10 119.8(4) . . ?
C13 C12 C11 121.7(4) . . ?
C14 C13 C12 118.3(4) . . ?
C15 C14 C13 121.3(4) . . ?
C14 C15 C10 119.1(4) . . ?
C16 C15 C10 120.4(4) . . ?
C16 C15 C14 120.5(4) . . ?
F2 C16 F1 105.6(4) . . ?
F3 C16 F1 106.2(4) . . ?
F3 C16 F2 105.9(4) . . ?
C15 C16 F1 113.0(4) . . ?
C15 C16 F2 112.1(4) . . ?
C15 C16 F3 113.4(4) . . ?
C18 C17 N1 118.4(4) . . ?
C22 C17 N1 121.6(4) . . ?
C22 C17 C18 120.0(4) . . ?
C19 C18 C17 120.3(4) . . ?
C20 C19 C18 120.2(4) . . ?
C21 C20 C19 119.3(4) . . ?
C22 C21 C20 122.4(4) . . ?
C21 C22 C17 117.8(4) . . ?
F5 C23 F4 104.8(4) . . ?
F6 C23 F4 104.5(4) . . ?
F6 C23 F5 104.2(4) . . ?
F8 B1 F7 109.3(4) . . ?
F9 B1 F7 110.0(4) . . ?
F9 B1 F8 109.1(4) . . ?
F10 B1 F7 109.8(4) . . ?
F10 B1 F8 109.3(4) . . ?
F10 B1 F9 109.2(4) . . ?

_olex2_exptl_crystal_mounting_method 
'crystals were mounted using perfluoropolyalkylether from ABCR viscosity 1800 cts on to a cryoloop'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_equal_distance_atom_site_label_1
_restr_equal_distance_atom_site_label_2
_restr_equal_distance_site_symmetry_2
_restr_equal_distance_class_id
C23 C22 1 1
C23 C22 1 5
C23 C22 1 3
C23 F4 1 3
C23 F4 1 1
C23 F4 1 5
C23 F5 1 3
C23 F5 1 5
C23 F5 1 1
C23 F6 1 5
C23 F6 1 1
C23 F6 1 3
F4 F5 1 2
F4 F5 1 4
F4 F5 1 6
F4 F6 1 4
F4 F6 1 2
F4 F6 1 6
F6 F5 1 4
F6 F5 1 6
F6 F5 1 2

_iucr_refine_instructions_details 
'The proposed model includes two trifluromethyl groups. Similar, pseudo-threefold geometry was imposed on the disordered trifluromethyl groups using effective standard deviations of 0.01 and 0.02\%A for bond lengths and angles, respectively.'

loop_
_restr_equal_distance_class_class_id
_restr_equal_distance_class_target_weight_param
_restr_equal_distance_class_average
_restr_equal_distance_class_esd
_restr_equal_distance_class_diff_max
1 0.0200 1.3645 0.0594 0.1027
2 0.0200 2.1035 0.0026 0.0037
3 0.0200 1.3645 0.0594 0.1027
4 0.0200 2.1035 0.0026 0.0037
5 0.0200 1.3645 0.0594 0.1027
6 0.0200 2.1035 0.0026 0.0037

