# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

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

data_007a-17123
_database_code_depnum_ccdc_archive 'CCDC 1954011'
loop_
_audit_author_name
_audit_author_address
'Brandon Mercado'
;Yale University
United States of America
;
_audit_update_record             
;
2019-09-17 deposited with the CCDC.	2019-12-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H20 N2 Ni O2'
_chemical_formula_sum            'C16 H20 N2 Ni O2'
_chemical_formula_weight         331.05

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   14.557(3)
_cell_length_b                   10.2366(5)
_cell_length_c                   8.2137(14)
_cell_angle_alpha                90
_cell_angle_beta                 141.27(4)
_cell_angle_gamma                90
_cell_volume                     765.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    17033
_cell_measurement_theta_min      5.6480
_cell_measurement_theta_max      66.7830

_exptl_crystal_description       Plate
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_F_000             348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.871
_shelx_estimated_absorpt_T_min   0.706
_shelx_estimated_absorpt_T_max   0.706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.75022
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.16b (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'microfocus rotating anode'
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 22.2
_diffrn_reflns_number            21932
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         5.698
_diffrn_reflns_theta_max         66.757
_diffrn_reflns_theta_full        66.757
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1361
_reflns_number_gt                1234
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB-2014/2 (Sheldrick, 2014)'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
  
The hydrogen atoms were first found in the difference map, then generated 
geometrically and refined as riding atoms with C-H distances = 0.95 - 0.99 
angstroms and Uiso(H) = 1.2 times Ueq(C) for CH and CH2 groups and Uiso(H) 
= 1.5 times Ueq(C) for CH3 groups. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0353P)²+0.5259P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     SHELXT
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1361
_refine_ls_number_parameters     99
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0281
_refine_ls_wR_factor_ref         0.0733
_refine_ls_wR_factor_gt          0.0708
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.5000 0.5000 0.5000 0.01420(15) Uani 1 2 d S . P . .
O1 O 0.61978(12) 0.41491(12) 0.8109(2) 0.0192(3) Uani 1 1 d . . . . .
N1 N 0.61660(15) 0.42374(13) 0.4996(3) 0.0149(3) Uani 1 1 d . . . . .
C1 C 0.58829(19) 0.42342(16) 0.2991(3) 0.0173(4) Uani 1 1 d . . . . .
H1 H 0.4999 0.4620 0.1386 0.021 Uiso 1 1 calc R U . . .
C5 C 0.74030(18) 0.36732(16) 0.7273(3) 0.0162(4) Uani 1 1 d . . . . .
C6 C 0.75475(18) 0.37254(18) 0.9312(3) 0.0185(4) Uani 1 1 d . . . . .
C4 C 0.84216(19) 0.31222(18) 0.7619(3) 0.0207(4) Uani 1 1 d . . . . .
H4 H 0.9301 0.2743 0.9240 0.025 Uiso 1 1 calc R U . . .
C2 C 0.68404(19) 0.36873(17) 0.3204(3) 0.0211(4) Uani 1 1 d . . . . .
H2 H 0.6620 0.3688 0.1769 0.025 Uiso 1 1 calc R U . . .
C3 C 0.8134(2) 0.31360(18) 0.5569(4) 0.0231(4) Uani 1 1 d . . . . .
H3 H 0.8820 0.2769 0.5777 0.028 Uiso 1 1 calc R U . . .
C7 C 0.7911(2) 0.2356(2) 1.0464(4) 0.0279(4) Uani 1 1 d . . . . .
H7A H 0.7978 0.2384 1.1747 0.042 Uiso 1 1 calc R U . . .
H7B H 0.8852 0.2066 1.1311 0.042 Uiso 1 1 calc R U . . .
H7C H 0.7136 0.1745 0.9069 0.042 Uiso 1 1 calc R U . . .
C8 C 0.8761(2) 0.4696(2) 1.1435(4) 0.0305(5) Uani 1 1 d . . . . .
H8A H 0.8538 0.5550 1.0647 0.046 Uiso 1 1 calc R U . . .
H8B H 0.9703 0.4381 1.2313 0.046 Uiso 1 1 calc R U . . .
H8C H 0.8820 0.4779 1.2704 0.046 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O1 1.8365(15) 3_666 ?
Ni1 O1 1.8365(15) . ?
Ni1 N1 1.8709(14) . ?
Ni1 N1 1.8709(14) 3_666 ?
O1 C6 1.413(2) . ?
N1 C5 1.349(2) . ?
N1 C1 1.350(2) . ?
C1 C2 1.380(2) . ?
C1 H1 0.9500 . ?
C5 C4 1.393(2) . ?
C5 C6 1.517(2) . ?
C6 C8 1.531(3) . ?
C6 C7 1.536(3) . ?
C4 C3 1.383(3) . ?
C4 H4 0.9500 . ?
C2 C3 1.389(3) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Ni1 O1 180.0 3_666 . ?
O1 Ni1 N1 94.24(6) 3_666 . ?
O1 Ni1 N1 85.76(6) . . ?
O1 Ni1 N1 85.76(6) 3_666 3_666 ?
O1 Ni1 N1 94.24(6) . 3_666 ?
N1 Ni1 N1 180.0 . 3_666 ?
C6 O1 Ni1 114.33(10) . . ?
C5 N1 C1 119.84(14) . . ?
C5 N1 Ni1 114.04(11) . . ?
C1 N1 Ni1 126.11(12) . . ?
N1 C1 C2 121.93(16) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
N1 C5 C4 120.87(16) . . ?
N1 C5 C6 113.66(14) . . ?
C4 C5 C6 125.46(16) . . ?
O1 C6 C5 108.61(14) . . ?
O1 C6 C8 109.70(15) . . ?
C5 C6 C8 108.86(15) . . ?
O1 C6 C7 109.51(14) . . ?
C5 C6 C7 109.40(14) . . ?
C8 C6 C7 110.71(16) . . ?
C3 C4 C5 118.99(17) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C1 C2 C3 118.38(16) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C4 C3 C2 119.95(16) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Ni1 O1 C6 17.81(11) . . . . ?
N1 Ni1 O1 C6 -162.19(11) 3_666 . . . ?
O1 Ni1 N1 C5 168.83(12) 3_666 . . . ?
O1 Ni1 N1 C5 -11.17(12) . . . . ?
O1 Ni1 N1 C1 -9.93(14) 3_666 . . . ?
O1 Ni1 N1 C1 170.07(14) . . . . ?
C5 N1 C1 C2 -1.2(2) . . . . ?
Ni1 N1 C1 C2 177.47(13) . . . . ?
C1 N1 C5 C4 2.1(2) . . . . ?
Ni1 N1 C5 C4 -176.71(13) . . . . ?
C1 N1 C5 C6 -178.53(15) . . . . ?
Ni1 N1 C5 C6 2.62(18) . . . . ?
Ni1 O1 C6 C5 -19.66(17) . . . . ?
Ni1 O1 C6 C8 99.22(15) . . . . ?
Ni1 O1 C6 C7 -139.08(12) . . . . ?
N1 C5 C6 O1 10.7(2) . . . . ?
C4 C5 C6 O1 -170.01(16) . . . . ?
N1 C5 C6 C8 -108.70(17) . . . . ?
C4 C5 C6 C8 70.6(2) . . . . ?
N1 C5 C6 C7 130.19(16) . . . . ?
C4 C5 C6 C7 -50.5(2) . . . . ?
N1 C5 C4 C3 -1.3(3) . . . . ?
C6 C5 C4 C3 179.41(17) . . . . ?
N1 C1 C2 C3 -0.5(3) . . . . ?
C5 C4 C3 C2 -0.4(3) . . . . ?
C1 C2 C3 C4 1.3(3) . . . . ?

_refine_diff_density_max         0.284
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_spider-16039
_database_code_depnum_ccdc_archive 'CCDC 1954013'
loop_
_audit_author_name
_audit_author_address
'Brandon Mercado'
;Yale University
United States of America
;
_audit_update_record             
;
2019-09-17 deposited with the CCDC.	2019-12-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H28 N2 Ni O6'
_chemical_formula_sum            'C20 H28 N2 Ni O6'
_chemical_formula_weight         451.15

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   8.3939(4)
_cell_length_b                   14.9329(8)
_cell_length_c                   8.7611(6)
_cell_angle_alpha                90
_cell_angle_beta                 108.791(8)
_cell_angle_gamma                90
_cell_volume                     1039.63(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    11415
_cell_measurement_theta_min      3.7
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_F_000             476
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.972
_shelx_estimated_absorpt_T_min   0.829
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.778
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
; 
Olex2 1.2 
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506) 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  
; 
Olex2 1.2 
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506) 
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            20757
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_av_R_equivalents  0.0888
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.226
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_full        25.008
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1829
_reflns_number_gt                1536
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
  
The hydrogen atoms were first found in the difference map, then generated 
geometrically and refined as riding atoms with C-H distances = 0.95 - 0.99 
angstroms and Uiso(H) = 1.2 times Ueq(C) for CH and CH2 groups and Uiso(H) 
= 1.5 times Ueq(C) for CH3 groups. The proton on O1 was found in the 
difference map and freely refined.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0241P)²+1.4103P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     SHELXT
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1829
_refine_ls_number_parameters     140
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.0846
_refine_ls_wR_factor_gt          0.0800
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.5000 0.5000 0.5000 0.02152(16) Uani 1 2 d S . P . .
O1 O 0.7570(2) 0.51457(13) 0.5442(2) 0.0255(5) Uani 1 1 d . . . . .
H1 H 0.751(5) 0.532(2) 0.446(5) 0.058(12) Uiso 1 1 d . . . . .
O2 O 0.5536(2) 0.44009(13) 0.7246(2) 0.0302(5) Uani 1 1 d . . . . .
O3 O 0.2947(3) 0.43517(15) 0.7455(3) 0.0377(5) Uani 1 1 d . . . . .
N1 N 0.5371(3) 0.62376(14) 0.6043(3) 0.0217(5) Uani 1 1 d . . . . .
C1 C 0.4133(3) 0.67948(19) 0.6121(3) 0.0256(6) Uani 1 1 d . . . . .
H1A H 0.3004 0.6586 0.5745 0.031 Uiso 1 1 calc R U . . .
C2 C 0.4435(4) 0.76574(19) 0.6725(3) 0.0276(7) Uani 1 1 d . . . . .
H2 H 0.3534 0.8036 0.6749 0.033 Uiso 1 1 calc R U . . .
C3 C 0.6079(4) 0.79534(19) 0.7291(3) 0.0289(7) Uani 1 1 d . . . . .
H3 H 0.6326 0.8542 0.7711 0.035 Uiso 1 1 calc R U . . .
C4 C 0.7361(4) 0.73865(18) 0.7241(3) 0.0276(7) Uani 1 1 d . . . . .
H4 H 0.8498 0.7580 0.7640 0.033 Uiso 1 1 calc R U . . .
C5 C 0.6977(3) 0.65322(18) 0.6604(3) 0.0227(6) Uani 1 1 d . . . . .
C6 C 0.8333(3) 0.58669(18) 0.6532(3) 0.0256(6) Uani 1 1 d . . . . .
C7 C 0.9146(4) 0.5457(2) 0.8198(4) 0.0329(7) Uani 1 1 d . . . . .
H7A H 0.8303 0.5115 0.8508 0.049 Uiso 1 1 calc R U . . .
H7B H 0.9595 0.5935 0.8986 0.049 Uiso 1 1 calc R U . . .
H7C H 1.0064 0.5058 0.8171 0.049 Uiso 1 1 calc R U . . .
C8 C 0.9682(4) 0.6315(2) 0.5954(4) 0.0350(8) Uani 1 1 d . . . . .
H8A H 0.9142 0.6618 0.4924 0.053 Uiso 1 1 calc R U . . .
H8B H 1.0462 0.5859 0.5812 0.053 Uiso 1 1 calc R U . . .
H8C H 1.0303 0.6754 0.6757 0.053 Uiso 1 1 calc R U . . .
C9 C 0.4522(4) 0.42340(19) 0.8017(4) 0.0309(7) Uani 1 1 d . . . . .
C10 C 0.5251(4) 0.3880(2) 0.9721(4) 0.0386(8) Uani 1 1 d . . . . .
H10A H 0.6302 0.4196 1.0275 0.058 Uiso 1 1 calc R U . . .
H10B H 0.5478 0.3238 0.9689 0.058 Uiso 1 1 calc R U . . .
H10C H 0.4445 0.3977 1.0303 0.058 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 N1 2.041(2) . ?
Ni1 N1 2.041(2) 3_666 ?
Ni1 O2 2.0747(19) . ?
Ni1 O2 2.0747(19) 3_666 ?
Ni1 O1 2.0765(18) 3_666 ?
Ni1 O1 2.0765(18) . ?
O1 C6 1.445(3) . ?
O1 H1 0.89(4) . ?
O2 C9 1.270(3) . ?
O3 C9 1.266(4) . ?
N1 C1 1.351(3) . ?
N1 C5 1.351(3) . ?
C1 C2 1.384(4) . ?
C1 H1A 0.9500 . ?
C2 C3 1.380(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.381(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.527(4) . ?
C6 C7 1.526(4) . ?
C6 C8 1.535(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.515(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ni1 N1 180.0 . 3_666 ?
N1 Ni1 O2 90.60(8) . . ?
N1 Ni1 O2 89.40(8) 3_666 . ?
N1 Ni1 O2 89.40(8) . 3_666 ?
N1 Ni1 O2 90.60(8) 3_666 3_666 ?
O2 Ni1 O2 180.0 . 3_666 ?
N1 Ni1 O1 100.26(8) . 3_666 ?
N1 Ni1 O1 79.74(8) 3_666 3_666 ?
O2 Ni1 O1 91.52(8) . 3_666 ?
O2 Ni1 O1 88.48(8) 3_666 3_666 ?
N1 Ni1 O1 79.74(8) . . ?
N1 Ni1 O1 100.26(8) 3_666 . ?
O2 Ni1 O1 88.48(8) . . ?
O2 Ni1 O1 91.52(8) 3_666 . ?
O1 Ni1 O1 180.0 3_666 . ?
C6 O1 Ni1 114.47(15) . . ?
C6 O1 H1 108(2) . . ?
Ni1 O1 H1 97(2) . . ?
C9 O2 Ni1 127.70(19) . . ?
C1 N1 C5 118.4(2) . . ?
C1 N1 Ni1 124.86(19) . . ?
C5 N1 Ni1 116.64(17) . . ?
N1 C1 C2 122.9(3) . . ?
N1 C1 H1A 118.5 . . ?
C2 C1 H1A 118.5 . . ?
C3 C2 C1 118.3(3) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 119.4(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 119.6(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
N1 C5 C4 121.4(3) . . ?
N1 C5 C6 116.3(2) . . ?
C4 C5 C6 122.4(2) . . ?
O1 C6 C7 107.4(2) . . ?
O1 C6 C5 109.5(2) . . ?
C7 C6 C5 109.3(2) . . ?
O1 C6 C8 108.9(2) . . ?
C7 C6 C8 109.9(2) . . ?
C5 C6 C8 111.6(2) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O3 C9 O2 124.1(3) . . ?
O3 C9 C10 118.1(3) . . ?
O2 C9 C10 117.8(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
C5 N1 C1 C2 1.1(4) . . . . ?
Ni1 N1 C1 C2 -174.7(2) . . . . ?
N1 C1 C2 C3 -0.9(4) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C1 N1 C5 C4 -0.3(4) . . . . ?
Ni1 N1 C5 C4 175.8(2) . . . . ?
C1 N1 C5 C6 178.3(2) . . . . ?
Ni1 N1 C5 C6 -5.6(3) . . . . ?
C3 C4 C5 N1 -0.7(4) . . . . ?
C3 C4 C5 C6 -179.2(3) . . . . ?
Ni1 O1 C6 C7 98.6(2) . . . . ?
Ni1 O1 C6 C5 -20.1(3) . . . . ?
Ni1 O1 C6 C8 -142.40(19) . . . . ?
N1 C5 C6 O1 16.8(3) . . . . ?
C4 C5 C6 O1 -164.6(3) . . . . ?
N1 C5 C6 C7 -100.7(3) . . . . ?
C4 C5 C6 C7 77.9(3) . . . . ?
N1 C5 C6 C8 137.5(3) . . . . ?
C4 C5 C6 C8 -44.0(4) . . . . ?
Ni1 O2 C9 O3 5.8(4) . . . . ?
Ni1 O2 C9 C10 -173.61(19) . . . . ?

_refine_diff_density_max         0.303
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_007a-18050
_database_code_depnum_ccdc_archive 'CCDC 1954012'
loop_
_audit_author_name
_audit_author_address
'Brandon Mercado'
;Yale University
United States of America
;
_audit_update_record             
;
2019-09-17 deposited with the CCDC.	2019-12-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H30 N4 Ni O2, F6 P, C5 H5 N'
_chemical_formula_sum            'C31 H35 F6 N5 Ni O2 P'
_chemical_formula_weight         713.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

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

_cell_length_a                   22.4997(12)
_cell_length_b                   8.4913(3)
_cell_length_c                   17.7726(7)
_cell_angle_alpha                90
_cell_angle_beta                 111.646(5)
_cell_angle_gamma                90
_cell_volume                     3156.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    15415
_cell_measurement_theta_min      4.1760
_cell_measurement_theta_max      66.1460

_exptl_crystal_description       Plate
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_F_000             1476
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    2.017
_shelx_estimated_absorpt_T_min   0.824
_shelx_estimated_absorpt_T_max   0.906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.71733
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.16b (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'microfocus rotating anode'
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 22.2
_diffrn_reflns_number            54705
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_av_R_equivalents  0.0908
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.228
_diffrn_reflns_theta_max         66.893
_diffrn_reflns_theta_full        66.893
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2801
_reflns_number_gt                2231
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB-2014/2 (Sheldrick, 2014)'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
  
The hydrogen atoms were first found in the difference map, then generated 
geometrically and refined as riding atoms with C-H distances = 0.95 - 0.99 
angstroms and Uiso(H) = 1.2 times Ueq(C) for CH and CH2 groups and Uiso(H) 
= 1.5 times Ueq(C) for CH3 groups. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0632P)²+10.3170P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     SHELXT
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2801
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1434
_refine_ls_wR_factor_gt          0.1320
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.5000 0.5000 0.5000 0.0298(2) Uani 1 2 d S . P . .
O1 O 0.51000(11) 0.6437(3) 0.58131(13) 0.0325(5) Uani 1 1 d . . . . .
N1 N 0.43194(13) 0.4143(3) 0.52857(16) 0.0318(6) Uani 1 1 d . . . . .
N2 N 0.56538(13) 0.3428(3) 0.58781(16) 0.0328(7) Uani 1 1 d . . . . .
C1 C 0.39610(18) 0.2899(4) 0.4933(2) 0.0377(8) Uani 1 1 d . . . . .
H1 H 0.3993 0.2480 0.4454 0.045 Uiso 1 1 calc R U . . .
C2 C 0.35469(19) 0.2204(5) 0.5244(2) 0.0444(9) Uani 1 1 d . . . . .
H2 H 0.3292 0.1326 0.4984 0.053 Uiso 1 1 calc R U . . .
C3 C 0.3514(2) 0.2831(5) 0.5949(2) 0.0479(10) Uani 1 1 d . . . . .
H3 H 0.3242 0.2365 0.6189 0.057 Uiso 1 1 calc R U . . .
C4 C 0.38779(18) 0.4132(5) 0.6301(2) 0.0411(9) Uani 1 1 d . . . . .
H4 H 0.3855 0.4571 0.6781 0.049 Uiso 1 1 calc R U . . .
C5 C 0.42795(17) 0.4799(4) 0.5951(2) 0.0345(8) Uani 1 1 d . . . . .
C6 C 0.46829(17) 0.6259(4) 0.6245(2) 0.0353(8) Uani 1 1 d . . . . .
C7 C 0.5089(2) 0.6135(6) 0.7150(2) 0.0496(10) Uani 1 1 d . . . . .
H7A H 0.5330 0.5144 0.7256 0.074 Uiso 1 1 calc R U . . .
H7B H 0.4810 0.6157 0.7462 0.074 Uiso 1 1 calc R U . . .
H7C H 0.5388 0.7023 0.7312 0.074 Uiso 1 1 calc R U . . .
C8 C 0.42463(19) 0.7706(5) 0.6091(2) 0.0449(10) Uani 1 1 d . . . . .
H8A H 0.4508 0.8659 0.6255 0.067 Uiso 1 1 calc R U . . .
H8B H 0.3970 0.7614 0.6405 0.067 Uiso 1 1 calc R U . . .
H8C H 0.3982 0.7769 0.5513 0.067 Uiso 1 1 calc R U . . .
C9 C 0.55713(18) 0.1858(4) 0.5834(2) 0.0380(8) Uani 1 1 d . . . . .
H9 H 0.5228 0.1428 0.5390 0.046 Uiso 1 1 calc R U . . .
C10 C 0.59659(19) 0.0855(5) 0.6408(2) 0.0421(9) Uani 1 1 d . . . . .
H10 H 0.5891 -0.0249 0.6366 0.050 Uiso 1 1 calc R U . . .
C11 C 0.64696(18) 0.1464(5) 0.7041(2) 0.0397(9) Uani 1 1 d . . . . .
H11 H 0.6754 0.0790 0.7438 0.048 Uiso 1 1 calc R U . . .
C12 C 0.65560(18) 0.3080(5) 0.7093(2) 0.0398(9) Uani 1 1 d . . . . .
H12 H 0.6898 0.3534 0.7529 0.048 Uiso 1 1 calc R U . . .
C13 C 0.61391(16) 0.4017(5) 0.6502(2) 0.0359(8) Uani 1 1 d . . . . .
H13 H 0.6199 0.5126 0.6540 0.043 Uiso 1 1 calc R U . . .
P1 P 0.7500 0.7500 0.7500 0.0329(3) Uani 1 2 d S . P . .
F1 F 0.67421(10) 0.7628(2) 0.72397(13) 0.0450(5) Uani 1 1 d . . . . .
F2 F 0.75181(11) 0.6160(3) 0.81376(13) 0.0465(6) Uani 1 1 d . . . . .
F3 F 0.75902(10) 0.8814(2) 0.81759(12) 0.0438(5) Uani 1 1 d . . . . .
N14 N 0.2500 0.9119(7) 0.5000 0.0627(14) Uani 1 2 d S T P . .
C15 C 0.25994(18) 0.8306(5) 0.4390(2) 0.0434(9) Uani 1 1 d . . . . .
H15 H 0.2651 0.8860 0.3953 0.052 Uiso 1 1 calc R U . . .
C16 C 0.2625(2) 0.6723(6) 0.4410(3) 0.0579(13) Uani 1 1 d . . . . .
H16 H 0.2729 0.6161 0.4013 0.070 Uiso 1 1 calc R U . . .
C17 C 0.2500 0.5929(9) 0.5000 0.088(3) Uani 1 2 d S T P . .
H17 H 0.2500 0.4810 0.5000 0.105 Uiso 1 2 calc R U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O1 1.840(2) 5_666 ?
Ni1 O1 1.840(2) . ?
Ni1 N1 1.925(3) . ?
Ni1 N1 1.925(3) 5_666 ?
Ni1 N2 2.165(3) . ?
Ni1 N2 2.165(3) 5_666 ?
O1 C6 1.423(4) . ?
N1 C1 1.336(5) . ?
N1 C5 1.339(4) . ?
N2 C13 1.334(4) . ?
N2 C9 1.344(5) . ?
C1 C2 1.379(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.389(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.511(5) . ?
C6 C7 1.533(5) . ?
C6 C8 1.533(5) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.373(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.371(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.374(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
P1 F2 1.596(2) 7_666 ?
P1 F2 1.596(2) . ?
P1 F3 1.596(2) 7_666 ?
P1 F3 1.596(2) . ?
P1 F1 1.597(2) . ?
P1 F1 1.597(2) 7_666 ?
N14 C15 1.373(5) . ?
N14 C15 1.373(5) 2_556 ?
C15 C16 1.345(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.360(6) . ?
C16 H16 0.9500 . ?
C17 C16 1.360(6) 2_556 ?
C17 H17 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Ni1 O1 180.0 5_666 . ?
O1 Ni1 N1 94.46(11) 5_666 . ?
O1 Ni1 N1 85.54(11) . . ?
O1 Ni1 N1 85.54(11) 5_666 5_666 ?
O1 Ni1 N1 94.46(11) . 5_666 ?
N1 Ni1 N1 180.00(14) . 5_666 ?
O1 Ni1 N2 90.64(10) 5_666 . ?
O1 Ni1 N2 89.36(10) . . ?
N1 Ni1 N2 88.39(11) . . ?
N1 Ni1 N2 91.61(11) 5_666 . ?
O1 Ni1 N2 89.37(10) 5_666 5_666 ?
O1 Ni1 N2 90.63(10) . 5_666 ?
N1 Ni1 N2 91.61(11) . 5_666 ?
N1 Ni1 N2 88.39(11) 5_666 5_666 ?
N2 Ni1 N2 180.0 . 5_666 ?
C6 O1 Ni1 116.1(2) . . ?
C1 N1 C5 121.2(3) . . ?
C1 N1 Ni1 125.2(2) . . ?
C5 N1 Ni1 113.2(2) . . ?
C13 N2 C9 118.3(3) . . ?
C13 N2 Ni1 119.9(2) . . ?
C9 N2 Ni1 121.8(2) . . ?
N1 C1 C2 122.0(3) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C1 C2 C3 117.8(4) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
C4 C3 C2 119.7(4) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
N1 C5 C4 119.4(3) . . ?
N1 C5 C6 114.8(3) . . ?
C4 C5 C6 125.8(3) . . ?
O1 C6 C5 109.4(3) . . ?
O1 C6 C7 108.5(3) . . ?
C5 C6 C7 110.9(3) . . ?
O1 C6 C8 109.0(3) . . ?
C5 C6 C8 109.4(3) . . ?
C7 C6 C8 109.7(3) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 C10 122.3(4) . . ?
N2 C9 H9 118.8 . . ?
C10 C9 H9 118.8 . . ?
C11 C10 C9 119.2(4) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C12 118.8(3) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C13 C12 C11 118.9(4) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
N2 C13 C12 122.5(4) . . ?
N2 C13 H13 118.8 . . ?
C12 C13 H13 118.8 . . ?
F2 P1 F2 180.0 7_666 . ?
F2 P1 F3 90.06(11) 7_666 7_666 ?
F2 P1 F3 89.94(11) . 7_666 ?
F2 P1 F3 89.94(11) 7_666 . ?
F2 P1 F3 90.06(11) . . ?
F3 P1 F3 180.00(11) 7_666 . ?
F2 P1 F1 90.06(11) 7_666 . ?
F2 P1 F1 89.95(12) . . ?
F3 P1 F1 90.21(11) 7_666 . ?
F3 P1 F1 89.79(11) . . ?
F2 P1 F1 89.94(12) 7_666 7_666 ?
F2 P1 F1 90.06(11) . 7_666 ?
F3 P1 F1 89.79(11) 7_666 7_666 ?
F3 P1 F1 90.21(11) . 7_666 ?
F1 P1 F1 180.0 . 7_666 ?
C15 N14 C15 119.5(5) . 2_556 ?
C16 C15 N14 119.9(4) . . ?
C16 C15 H15 120.0 . . ?
N14 C15 H15 120.0 . . ?
C15 C16 C17 119.8(5) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C16 120.6(7) . 2_556 ?
C16 C17 H17 119.7 . . ?
C16 C17 H17 119.7 2_556 . ?

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 Ni1 O1 C6 1.1(2) . . . . ?
N1 Ni1 O1 C6 -178.9(2) 5_666 . . . ?
N2 Ni1 O1 C6 -87.3(2) . . . . ?
N2 Ni1 O1 C6 92.6(2) 5_666 . . . ?
C5 N1 C1 C2 -1.7(6) . . . . ?
Ni1 N1 C1 C2 170.1(3) . . . . ?
N1 C1 C2 C3 -0.5(6) . . . . ?
C1 C2 C3 C4 1.6(6) . . . . ?
C2 C3 C4 C5 -0.6(6) . . . . ?
C1 N1 C5 C4 2.8(5) . . . . ?
Ni1 N1 C5 C4 -170.0(3) . . . . ?
C1 N1 C5 C6 -176.2(3) . . . . ?
Ni1 N1 C5 C6 11.0(4) . . . . ?
C3 C4 C5 N1 -1.6(6) . . . . ?
C3 C4 C5 C6 177.2(3) . . . . ?
Ni1 O1 C6 C5 4.2(3) . . . . ?
Ni1 O1 C6 C7 125.3(3) . . . . ?
Ni1 O1 C6 C8 -115.3(3) . . . . ?
N1 C5 C6 O1 -10.0(4) . . . . ?
C4 C5 C6 O1 171.1(3) . . . . ?
N1 C5 C6 C7 -129.5(3) . . . . ?
C4 C5 C6 C7 51.6(5) . . . . ?
N1 C5 C6 C8 109.3(3) . . . . ?
C4 C5 C6 C8 -69.6(4) . . . . ?
C13 N2 C9 C10 0.3(5) . . . . ?
Ni1 N2 C9 C10 -177.0(3) . . . . ?
N2 C9 C10 C11 -1.2(6) . . . . ?
C9 C10 C11 C12 1.5(5) . . . . ?
C10 C11 C12 C13 -0.8(5) . . . . ?
C9 N2 C13 C12 0.5(5) . . . . ?
Ni1 N2 C13 C12 177.7(3) . . . . ?
C11 C12 C13 N2 -0.2(6) . . . . ?
C15 N14 C15 C16 -2.7(3) 2_556 . . . ?
N14 C15 C16 C17 5.3(6) . . . . ?
C15 C16 C17 C16 -2.7(3) . . . 2_556 ?

_refine_diff_density_max         0.487
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.071

