# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_qj07113
_database_code_depnum_ccdc_archive 'CCDC 726796'
_audit_update_record             
;
2018-05-17 deposited with the CCDC.
2018-05-24 downloaded from the CCDC.
;
_audit_creation_date             2018-05-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H24 Cd N12, 2(F), 2(H2 O)'
_chemical_formula_sum            'C18 H28 Cd F2 N12 O2'
_chemical_formula_weight         594.92
_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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 '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                   9.5545(19)
_cell_length_b                   16.926(3)
_cell_length_c                   7.8873(16)
_cell_angle_alpha                90
_cell_angle_beta                 90.72(3)
_cell_angle_gamma                90
_cell_volume                     1275.4(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      4
_shelx_estimated_absorpt_T_max   0.875
_shelx_estimated_absorpt_T_min   0.818
_exptl_absorpt_coefficient_mu    0.911
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             604
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_Laue_measured_fraction_full 0.701
_diffrn_reflns_Laue_measured_fraction_max 0.720
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5646
_diffrn_reflns_point_group_measured_fraction_full 0.701
_diffrn_reflns_point_group_measured_fraction_max 0.720
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.918
_diffrn_reflns_theta_min         2.132
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.701
_diffrn_measured_fraction_theta_max 0.720
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4 diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1625
_reflns_number_total             2210
_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       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'NRCVAX (Gabe et al., 1989)'
_computing_molecular_graphics    ?
_computing_publication_material  'CIFTAB (Sheldrick, 2014)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0305(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   0.947
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0248
_refine_ls_restrained_S_all      0.947
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0242P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0617
_refine_ls_wR_factor_ref         0.0661
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O1W(H1WA,H1WB)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N4(H4), N6(H6), C1(H1), C2(H2A), C3(H3), C4(H4A), C5(H5), C6(H6A),
 C7(H7), C8(H8), C9(H9)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
Cd1 Cd 0.500000 0.000000 0.000000 0.03686(11) Uani 1 2 d S T P . .
N1 N 0.3651(2) 0.07003(12) 0.1948(3) 0.0468(5) Uani 1 1 d . . . . .
N2 N 0.2301(2) 0.16009(13) 0.3045(3) 0.0564(6) Uani 1 1 d . . . . .
H2 H 0.181780 0.202698 0.313833 0.068 Uiso 1 1 calc R . . . .
N3 N 0.7018(2) 0.02490(12) 0.1693(3) 0.0458(5) Uani 1 1 d . . . . .
N4 N 0.8467(2) 0.09430(14) 0.3265(3) 0.0580(6) Uani 1 1 d . . . . .
H4 H 0.877573 0.130319 0.394145 0.070 Uiso 1 1 calc R . . . .
N5 N 0.5579(2) 0.11813(11) -0.1443(3) 0.0431(4) Uani 1 1 d . . . . .
N6 N 0.6957(2) 0.19007(12) -0.3014(3) 0.0528(5) Uani 1 1 d . . . . .
H6 H 0.770867 0.209670 -0.342966 0.063 Uiso 1 1 calc R . . . .
C1 C 0.2999(3) 0.13706(15) 0.1690(4) 0.0516(6) Uani 1 1 d . . . . .
H1 H 0.302189 0.165133 0.067694 0.062 Uiso 1 1 calc R . . . .
C2 C 0.2489(3) 0.1042(2) 0.4258(4) 0.0631(8) Uani 1 1 d . . . . .
H2A H 0.211768 0.103771 0.534184 0.076 Uiso 1 1 calc R . . . .
C3 C 0.3329(3) 0.04930(17) 0.3561(3) 0.0548(6) Uani 1 1 d . . . . .
H3 H 0.364261 0.003788 0.410623 0.066 Uiso 1 1 calc R . . . .
C4 C 0.7151(3) 0.08557(15) 0.2723(4) 0.0513(6) Uani 1 1 d . . . . .
H4A H 0.641654 0.118345 0.303462 0.062 Uiso 1 1 calc R . . . .
C5 C 0.8330(3) -0.00629(15) 0.1584(5) 0.0598(8) Uani 1 1 d . . . . .
H5 H 0.857027 -0.050102 0.093856 0.072 Uiso 1 1 calc R . . . .
C6 C 0.9224(3) 0.0361(2) 0.2555(5) 0.0720(9) Uani 1 1 d . . . . .
H6A H 1.017765 0.026969 0.270539 0.086 Uiso 1 1 calc R . . . .
C7 C 0.6880(3) 0.13614(15) -0.1790(4) 0.0508(6) Uani 1 1 d . . . . .
H7 H 0.765489 0.113900 -0.124756 0.061 Uiso 1 1 calc R . . . .
C8 C 0.4796(3) 0.16351(15) -0.2511(4) 0.0533(6) Uani 1 1 d . . . . .
H8 H 0.382355 0.163703 -0.256612 0.064 Uiso 1 1 calc R . . . .
C9 C 0.5633(3) 0.20810(17) -0.3475(4) 0.0629(7) Uani 1 1 d . . . . .
H9 H 0.535416 0.244291 -0.429996 0.075 Uiso 1 1 calc R . . . .
F1 F 0.93044(17) 0.20960(11) -0.4610(2) 0.0692(5) Uani 1 1 d . . . . .
O1W O 0.0741(2) 0.20240(12) 0.8308(3) 0.0620(5) Uani 1 1 d . . . . .
H1WA H 0.022703 0.202607 0.742012 0.093 Uiso 1 1 d G . . . .
H1WB H 0.022242 0.221175 0.907713 0.093 Uiso 1 1 d G . . . .


_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
Cd1 N1 2.340(2) 3_655 ?
Cd1 N1 2.340(2) . ?
Cd1 N3 2.369(2) 3_655 ?
Cd1 N3 2.369(2) . ?
Cd1 N5 2.3694(18) 3_655 ?
Cd1 N5 2.3694(19) . ?
N1 C1 1.309(3) . ?
N1 C3 1.358(3) . ?
N2 C1 1.326(4) . ?
N2 C2 1.356(4) . ?
N3 C4 1.315(3) . ?
N3 C5 1.364(4) . ?
N4 C4 1.331(3) . ?
N4 C6 1.349(4) . ?
N5 C7 1.312(3) . ?
N5 C8 1.357(3) . ?
N6 C7 1.331(3) . ?
N6 C9 1.347(4) . ?
C2 C3 1.349(4) . ?
C5 C6 1.347(4) . ?
C8 C9 1.343(4) . ?

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 Cd1 N1 180.0 3_655 . ?
N1 Cd1 N3 89.47(7) . . ?
N1 Cd1 N3 90.53(7) . 3_655 ?
N1 Cd1 N3 90.53(7) 3_655 . ?
N1 Cd1 N3 89.47(7) 3_655 3_655 ?
N1 Cd1 N5 91.24(7) . . ?
N1 Cd1 N5 88.76(7) . 3_655 ?
N1 Cd1 N5 91.24(7) 3_655 3_655 ?
N1 Cd1 N5 88.76(7) 3_655 . ?
N3 Cd1 N3 180.0 . 3_655 ?
N3 Cd1 N5 94.17(7) 3_655 . ?
N3 Cd1 N5 85.83(7) 3_655 3_655 ?
N3 Cd1 N5 94.17(7) . 3_655 ?
N3 Cd1 N5 85.83(7) . . ?
N5 Cd1 N5 180.0 . 3_655 ?
C1 N1 Cd1 126.99(19) . . ?
C1 N1 C3 104.9(2) . . ?
C3 N1 Cd1 128.10(18) . . ?
C1 N2 C2 107.5(2) . . ?
C4 N3 Cd1 123.99(17) . . ?
C4 N3 C5 105.0(2) . . ?
C5 N3 Cd1 129.63(19) . . ?
C4 N4 C6 107.2(2) . . ?
C7 N5 Cd1 121.59(16) . . ?
C7 N5 C8 104.8(2) . . ?
C8 N5 Cd1 130.20(16) . . ?
C7 N6 C9 106.9(2) . . ?
N1 C1 N2 111.9(3) . . ?
C3 C2 N2 105.5(3) . . ?
C2 C3 N1 110.3(3) . . ?
N3 C4 N4 111.6(3) . . ?
C6 C5 N3 109.6(3) . . ?
C5 C6 N4 106.6(3) . . ?
N5 C7 N6 111.8(2) . . ?
C9 C8 N5 110.0(2) . . ?
C8 C9 N6 106.5(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1W 0.86 1.91 2.773(3) 179.1 4_565
N4 H4 F1 0.86 1.83 2.688(3) 175.9 1_556
N6 H6 F1 0.86 1.80 2.607(3) 156.3 .

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
Cd1 N1 C1 N2 178.59(16) . . . . ?
Cd1 N1 C3 C2 -178.02(16) . . . . ?
Cd1 N3 C4 N4 -167.78(18) . . . . ?
Cd1 N3 C5 C6 167.1(2) . . . . ?
Cd1 N5 C7 N6 160.95(17) . . . . ?
Cd1 N5 C8 C9 -158.9(2) . . . . ?
N2 C2 C3 N1 -0.4(3) . . . . ?
N3 C5 C6 N4 -0.3(4) . . . . ?
N5 C8 C9 N6 0.4(3) . . . . ?
C1 N1 C3 C2 -0.2(3) . . . . ?
C1 N2 C2 C3 0.8(3) . . . . ?
C2 N2 C1 N1 -1.0(3) . . . . ?
C3 N1 C1 N2 0.7(3) . . . . ?
C4 N3 C5 C6 0.2(4) . . . . ?
C4 N4 C6 C5 0.4(4) . . . . ?
C5 N3 C4 N4 0.0(3) . . . . ?
C6 N4 C4 N3 -0.3(4) . . . . ?
C7 N5 C8 C9 -0.2(3) . . . . ?
C7 N6 C9 C8 -0.4(3) . . . . ?
C8 N5 C7 N6 0.0(3) . . . . ?
C9 N6 C7 N5 0.3(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_qj07114
_database_code_depnum_ccdc_archive 'CCDC 726798'
_audit_update_record             
;
2018-05-17 deposited with the CCDC.
2018-05-24 downloaded from the CCDC.
;
_audit_creation_date             2018-05-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C18 H24 Co1 N12, 1(F), 2(N0.5 O1.5), 0.67(H12 O6)'
_chemical_formula_sum            'C18 H32 Co F N13 O7'
_chemical_formula_weight         620.49
_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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 '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      hexagonal
_space_group_IT_number           176
_space_group_name_H-M_alt        'P 63/m'
_space_group_name_Hall           '-P 6c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, z+1/2'
'y, -x+y, z+1/2'
'x-y, x, z+1/2'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'x, y, -z-1/2'
'-y, x-y, -z-1/2'
'-x+y, -x, -z-1/2'

_cell_length_a                   8.9720(13)
_cell_length_b                   8.9720(13)
_cell_length_c                   21.077(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1469.3(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      4
_shelx_estimated_absorpt_T_max   0.887
_shelx_estimated_absorpt_T_min   0.865
_exptl_absorpt_coefficient_mu    0.649
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Pink
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             646
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9619
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.240
_diffrn_reflns_theta_min         1.932
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4 diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                971
_reflns_number_total             1251
_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       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'NRCVAX (Gabe et al., 1989)'
_computing_molecular_graphics    ?
_computing_publication_material  'CIFTAB (Sheldrick, 2014)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.668
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     66
_refine_ls_number_reflns         1251
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0663P)²+0.4210P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1200
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All O(H,H) groups
2. Others
 Fixed Sof: H1WA(0.16667) H1WB(0.16667) H2WA(0.5)
3.a Riding coordinates:
 O1W(H1WA,H1WB), O2W(H2WA,H2WB)
3.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C3(H3)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
Co1 Co 0.000000 0.000000 0.000000 0.0343(2) Uani 1 6 d S T P . .
N1 N 0.1990(2) 0.1942(2) 0.05916(7) 0.0412(4) Uani 1 1 d . . . . .
N2 N 0.3765(2) 0.3193(3) 0.13862(9) 0.0516(5) Uani 1 1 d . . . . .
H2 H 0.429895 0.332304 0.173879 0.062 Uiso 1 1 calc R . . . .
C1 C 0.3998(3) 0.4451(3) 0.09763(13) 0.0650(7) Uani 1 1 d . . . . .
H1 H 0.476224 0.562297 0.102262 0.078 Uiso 1 1 calc R . . . .
C2 C 0.2914(3) 0.3682(3) 0.04894(11) 0.0553(6) Uani 1 1 d . . . . .
H2A H 0.280697 0.424554 0.013691 0.066 Uiso 1 1 calc R . . . .
C3 C 0.2552(3) 0.1715(3) 0.11398(10) 0.0452(5) Uani 1 1 d . . . . .
H3 H 0.214883 0.064770 0.133189 0.054 Uiso 1 1 calc R . . . .
F1 F 1.000000 1.000000 0.250000 0.0924(14) Uani 1 6 d S T P . .
N3 N 0.666667 0.333333 0.250000 0.0433(9) Uani 1 6 d S T P . .
O1 O 0.8285(2) 0.4393(3) 0.250000 0.0461(5) Uani 1 2 d S T P . .
O1W O 0.333333 0.666667 0.250000 0.167(5) Uani 1 6 d S T P . .
H1WA H 0.333333 0.666667 0.209670 0.200 Uiso 0.5 3 d RS T P . .
H1WB H 0.370820 0.596410 0.250000 0.200 Uiso 0.3333 2 d RS T P . .
O2W O 0.6703(4) 0.7314(4) 0.250000 0.1146(14) Uani 1 2 d S T P . .
H2WA H 0.627028 0.707096 0.212980 0.137 Uiso 0.5 1 d R . . . .
H2WB H 0.660338 0.632076 0.250000 0.137 Uiso 1 2 d RS T 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
Co1 N1 2.1604(16) 7 ?
Co1 N1 2.1604(16) . ?
Co1 N1 2.1604(16) 8 ?
Co1 N1 2.1604(16) 9 ?
Co1 N1 2.1604(16) 3 ?
Co1 N1 2.1604(16) 2 ?
N1 C2 1.370(3) . ?
N1 C3 1.317(3) . ?
N2 C1 1.352(3) . ?
N2 C3 1.330(3) . ?
C1 C2 1.343(3) . ?
N3 O1 1.2775(18) . ?
N3 O1 1.2775(18) 2_655 ?
N3 O1 1.2775(18) 3_665 ?

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 Co1 N1 90.02(6) 7 9 ?
N1 Co1 N1 89.98(6) 3 8 ?
N1 Co1 N1 90.02(6) 2 . ?
N1 Co1 N1 89.98(6) 7 3 ?
N1 Co1 N1 180.0 7 . ?
N1 Co1 N1 180.00(10) 9 3 ?
N1 Co1 N1 90.02(6) 9 8 ?
N1 Co1 N1 89.98(6) 7 2 ?
N1 Co1 N1 180.00(9) 2 8 ?
N1 Co1 N1 89.98(6) 9 2 ?
N1 Co1 N1 89.98(6) 9 . ?
N1 Co1 N1 90.02(6) 3 2 ?
N1 Co1 N1 89.98(6) 8 . ?
N1 Co1 N1 90.02(6) 7 8 ?
N1 Co1 N1 90.02(6) 3 . ?
C2 N1 Co1 127.86(14) . . ?
C3 N1 Co1 127.40(14) . . ?
C3 N1 C2 104.72(17) . . ?
C3 N2 C1 106.90(18) . . ?
C2 C1 N2 106.8(2) . . ?
C1 C2 N1 109.6(2) . . ?
N1 C3 N2 111.95(19) . . ?
O1 N3 O1 120.002(1) 3_665 2_655 ?
O1 N3 O1 120.000(1) . 2_655 ?
O1 N3 O1 119.998(1) . 3_665 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 N3 0.86 2.66 3.4607(18) 155.8 .
N2 H2 O1 0.86 1.90 2.757(2) 173.3 2_655
O1W H1WB O2W 0.85 2.33 2.779(3) 113.3 .
O2W H2WB O1 0.85 1.90 2.715(3) 161.1 2_655

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
Co1 N1 C2 C1 178.38(17) . . . . ?
Co1 N1 C3 N2 -178.60(13) . . . . ?
N2 C1 C2 N1 0.3(3) . . . . ?
C1 N2 C3 N1 0.3(3) . . . . ?
C2 N1 C3 N2 -0.1(2) . . . . ?
C3 N1 C2 C1 -0.1(3) . . . . ?
C3 N2 C1 C2 -0.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_qj0794
_database_code_depnum_ccdc_archive 'CCDC 726797'
_audit_update_record             
;
2018-05-17 deposited with the CCDC.
2018-05-24 downloaded from the CCDC.
;
_audit_creation_date             2018-05-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H24 N12 Ni, 2(F), 5(H2 O)'
_chemical_formula_sum            'C18 H34 F2 N12 Ni O5'
_chemical_formula_weight         595.28
_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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   8.9000(18)
_cell_length_b                   21.140(4)
_cell_length_c                   15.030(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2827.8(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      4
_shelx_estimated_absorpt_T_max   0.846
_shelx_estimated_absorpt_T_min   0.806
_exptl_absorpt_coefficient_mu    0.750
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Purple
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0134
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            36520
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.330
_diffrn_reflns_theta_min         1.662
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4 diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2691
_reflns_number_total             3569
_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       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'NRCVAX (Gabe et al., 1989)'
_computing_molecular_graphics    ?
_computing_publication_material  'CIFTAB (Sheldrick, 2014)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0029(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3569
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0274
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0450P)²+0.6140P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0869
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All O(H,H) groups
2.a Riding coordinates:
 O1W(H1WA,H1WB), O2W(H2WA,H2WB), O3W(H3WA,H3WB), O4W(H4WA,H4WB), O5W(H5WA,H5WB)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N4(H4), N6(H6), C1(H1), C2(H2A), C3(H3), C4(H4A), C5(H5), C6(H6A),
 C7(H7), C8(H8), C9(H9)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 1.000000 0.000000 0.000000 0.03265(9) Uani 1 2 d S T P . .
N1 N 0.80066(14) -0.05357(6) 0.00209(7) 0.0404(3) Uani 1 1 d . . . . .
N2 N 0.65404(16) -0.13596(7) -0.01297(9) 0.0525(3) Uani 1 1 d . . . . .
H2 H 0.620516 -0.171788 -0.031410 0.063 Uiso 1 1 calc R . . . .
N3 N 0.91049(13) 0.06100(5) -0.09917(7) 0.0381(3) Uani 1 1 d . . . . .
N4 N 0.88514(15) 0.13936(6) -0.19379(8) 0.0487(3) Uani 1 1 d . . . . .
H4 H 0.903602 0.173666 -0.222537 0.058 Uiso 1 1 calc R . . . .
N5 N 0.91314(13) 0.06013(5) 0.10011(8) 0.0408(3) Uani 1 1 d . . . . .
N6 N 0.80149(16) 0.13981(6) 0.16482(9) 0.0570(4) Uani 1 1 d . . . . .
H6 H 0.748008 0.173331 0.171705 0.068 Uiso 1 1 calc R . . . .
C1 C 0.78110(17) -0.10831(7) -0.03732(10) 0.0448(3) Uani 1 1 d . . . . .
H1 H 0.848643 -0.125697 -0.077697 0.054 Uiso 1 1 calc R . . . .
C2 C 0.6772(2) -0.04670(8) 0.05486(14) 0.0640(5) Uani 1 1 d . . . . .
H2A H 0.658164 -0.012100 0.091389 0.077 Uiso 1 1 calc R . . . .
C3 C 0.5873(2) -0.09710(10) 0.04632(16) 0.0741(6) Uani 1 1 d . . . . .
H3 H 0.496587 -0.104001 0.075512 0.089 Uiso 1 1 calc R . . . .
C4 C 0.96904(16) 0.11378(7) -0.13007(9) 0.0411(3) Uani 1 1 d . . . . .
H4A H 1.058672 0.131151 -0.109703 0.049 Uiso 1 1 calc R . . . .
C5 C 0.78080(19) 0.05332(8) -0.14656(11) 0.0559(4) Uani 1 1 d . . . . .
H5 H 0.713371 0.020066 -0.139705 0.067 Uiso 1 1 calc R . . . .
C6 C 0.7658(2) 0.10114(9) -0.20450(12) 0.0660(5) Uani 1 1 d . . . . .
H6A H 0.687365 0.106803 -0.244618 0.079 Uiso 1 1 calc R . . . .
C7 C 0.82976(17) 0.11047(7) 0.08852(10) 0.0474(3) Uani 1 1 d . . . . .
H7 H 0.794573 0.124057 0.033477 0.057 Uiso 1 1 calc R . . . .
C8 C 0.9400(2) 0.05813(8) 0.18972(11) 0.0614(4) Uani 1 1 d . . . . .
H8 H 0.996661 0.027435 0.218720 0.074 Uiso 1 1 calc R . . . .
C9 C 0.8721(3) 0.10731(10) 0.22923(12) 0.0740(6) Uani 1 1 d . . . . .
H9 H 0.873538 0.117027 0.289574 0.089 Uiso 1 1 calc R . . . .
F1 F 0.45462(15) 0.250000 0.78153(8) 0.0552(3) Uani 1 2 d S T P . .
F2 F 0.41668(14) 0.250000 0.07371(8) 0.0532(3) Uani 1 2 d S T P . .
O1W O 0.13239(17) 0.250000 0.31191(10) 0.0492(4) Uani 1 2 d S T P . .
H1WA H 0.110756 0.250000 0.259631 0.059 Uiso 1 2 d RS T P . .
H1WB H 0.055256 0.250000 0.344201 0.059 Uiso 1 2 d RS T P . .
O2W O 0.6654(2) 0.250000 0.65502(12) 0.0759(5) Uani 1 2 d S T P . .
H2WA H 0.614535 0.250000 0.700736 0.091 Uiso 1 2 d RS T P . .
H2WB H 0.761155 0.250000 0.669816 0.091 Uiso 1 2 d RS T P . .
O3W O 0.1343(2) 0.250000 0.56450(14) 0.1039(8) Uani 1 2 d S T P . .
H3WA H 0.080093 0.250000 0.527502 0.125 Uiso 1 2 d RS T P . .
H3WB H 0.078093 0.250000 0.610512 0.125 Uiso 1 2 d RS T P . .
O4W O 0.4499(3) 0.250000 0.51447(12) 0.0758(6) Uani 1 2 d S T P . .
H4WA H 0.508066 0.250000 0.559179 0.091 Uiso 1 2 d RS T P . .
H4WB H 0.373956 0.250000 0.530739 0.091 Uiso 1 2 d RS T P . .
O5W O 0.1252(2) 0.250000 0.13554(12) 0.0851(6) Uani 1 2 d S T P . .
H5WA H 0.204471 0.250000 0.120377 0.102 Uiso 1 2 d RS T P . .
H5WB H 0.063911 0.250000 0.093497 0.102 Uiso 1 2 d RS T 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 N1 2.1050(13) . ?
Ni1 N1 2.1051(13) 5_755 ?
Ni1 N3 2.1258(11) . ?
Ni1 N3 2.1257(11) 5_755 ?
Ni1 N5 2.1160(11) 5_755 ?
Ni1 N5 2.1160(11) . ?
N1 C1 1.3114(19) . ?
N1 C2 1.363(2) . ?
N2 C1 1.3245(19) . ?
N2 C3 1.350(2) . ?
N3 C4 1.3162(18) . ?
N3 C5 1.3660(19) . ?
N4 C4 1.3294(18) . ?
N4 C6 1.344(2) . ?
N5 C7 1.3091(19) . ?
N5 C8 1.369(2) . ?
N6 C7 1.3278(19) . ?
N6 C9 1.343(2) . ?
C2 C3 1.339(2) . ?
C5 C6 1.341(2) . ?
C8 C9 1.342(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ni1 N1 180.0 . 5_755 ?
N1 Ni1 N3 91.20(4) . . ?
N1 Ni1 N3 88.80(4) 5_755 . ?
N1 Ni1 N3 88.80(4) . 5_755 ?
N1 Ni1 N3 91.20(4) 5_755 5_755 ?
N1 Ni1 N5 89.73(5) . 5_755 ?
N1 Ni1 N5 90.27(5) . . ?
N1 Ni1 N5 89.73(5) 5_755 . ?
N1 Ni1 N5 90.27(5) 5_755 5_755 ?
N3 Ni1 N3 180.0 5_755 . ?
N5 Ni1 N3 89.85(5) . . ?
N5 Ni1 N3 90.15(5) . 5_755 ?
N5 Ni1 N3 90.15(5) 5_755 . ?
N5 Ni1 N3 89.85(5) 5_755 5_755 ?
N5 Ni1 N5 180.0 5_755 . ?
C1 N1 Ni1 125.44(10) . . ?
C1 N1 C2 104.47(13) . . ?
C2 N1 Ni1 129.11(11) . . ?
C1 N2 C3 106.85(14) . . ?
C4 N3 Ni1 127.83(10) . . ?
C4 N3 C5 104.55(12) . . ?
C5 N3 Ni1 127.60(10) . . ?
C4 N4 C6 106.59(13) . . ?
C7 N5 Ni1 126.93(10) . . ?
C7 N5 C8 104.79(13) . . ?
C8 N5 Ni1 128.12(11) . . ?
C7 N6 C9 107.16(14) . . ?
N1 C1 N2 112.21(14) . . ?
C3 C2 N1 109.95(16) . . ?
C2 C3 N2 106.53(16) . . ?
N3 C4 N4 112.13(13) . . ?
C6 C5 N3 109.47(15) . . ?
C5 C6 N4 107.25(14) . . ?
N5 C7 N6 111.84(14) . . ?
C9 C8 N5 109.44(16) . . ?
C8 C9 N6 106.75(15) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 F2 0.86 1.80 2.6537(15) 170.2 5_655
N4 H4 F1 0.86 1.90 2.7553(15) 176.6 6_656
N6 H6 O1W 0.86 1.94 2.7954(16) 178.5 6_656
O1W H1WA O5W 0.81 1.87 2.652(2) 162.3 .
O1W H1WB F2 0.84 1.74 2.577(2) 170.2 6_556
O2W H2WA F1 0.82 1.87 2.671(2) 163.8 .
O2W H2WB F1 0.88 1.87 2.745(2) 171.6 6_657
O3W H3WA F2 0.74 2.10 2.840(3) 177.3 6_556
O3W H3WB F1 0.85 1.96 2.813(3) 178.2 6_557
O4W H4WA O2W 0.85 2.01 2.853(3) 173.4 .
O4W H4WB O3W 0.72 2.19 2.908(3) 173.5 .
O5W H5WA F2 0.74 2.01 2.756(2) 177.5 .
O5W H5WB O4W 0.83 1.91 2.741(3) 171.2 6_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
Ni1 N1 C1 N2 169.62(10) . . . . ?
Ni1 N1 C2 C3 -168.73(14) . . . . ?
Ni1 N3 C4 N4 178.32(9) . . . . ?
Ni1 N3 C5 C6 -178.27(12) . . . . ?
Ni1 N5 C7 N6 -176.24(10) . . . . ?
Ni1 N5 C8 C9 175.59(13) . . . . ?
N1 C2 C3 N2 -0.5(2) . . . . ?
N3 C5 C6 N4 -0.3(2) . . . . ?
N5 C8 C9 N6 0.6(2) . . . . ?
C1 N1 C2 C3 0.2(2) . . . . ?
C1 N2 C3 C2 0.6(2) . . . . ?
C2 N1 C1 N2 0.12(18) . . . . ?
C3 N2 C1 N1 -0.43(19) . . . . ?
C4 N3 C5 C6 0.37(19) . . . . ?
C4 N4 C6 C5 0.1(2) . . . . ?
C5 N3 C4 N4 -0.31(16) . . . . ?
C6 N4 C4 N3 0.14(18) . . . . ?
C7 N5 C8 C9 0.0(2) . . . . ?
C7 N6 C9 C8 -0.9(2) . . . . ?
C8 N5 C7 N6 -0.57(18) . . . . ?
C9 N6 C7 N5 0.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
