# 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_5m5f
_database_code_depnum_ccdc_archive 'CCDC 784165'
_audit_update_record             
;
2018-03-13 deposited with the CCDC.
2018-04-26 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         'C10 H10 N2 O2'
_chemical_formula_sum            'C10 H10 N2 O2'
_chemical_formula_weight         190.20

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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, y+1/2, -z'

_cell_length_a                   7.3454(13)
_cell_length_b                   6.2161(10)
_cell_length_c                   10.7970(18)
_cell_angle_alpha                90
_cell_angle_beta                 108.144(15)
_cell_angle_gamma                90
_cell_volume                     468.48(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1386
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      27.48

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_F_000             200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'KUMA KM-4 with area CCD detector'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean '1024x1024 with blocks 2x2, 33.133pixel/mm'
_diffrn_reflns_number            6586
_diffrn_reflns_av_unetI/netI     0.0664
_diffrn_reflns_av_R_equivalents  0.0737
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.918
_diffrn_reflns_theta_max         27.477
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2123
_reflns_number_gt                1386
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.831
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'CrysAlis 1.171.32.6'
_computing_cell_refinement       'CrysAlis 1.171.32.6'
_computing_data_reduction        'CrysAlis 1.171.32.6'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1224P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.12(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2123
_refine_ls_number_parameters     129
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0673
_refine_ls_wR_factor_ref         0.1977
_refine_ls_wR_factor_gt          0.1840
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001

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
N1 N 0.2554(6) 0.4362(6) 0.3324(4) 0.0502(12) Uani 1 1 d . . . . .
H1 H 0.2707 0.3009 0.3224 0.060 Uiso 1 1 calc R U . . .
C2 C 0.1435(7) 0.5130(9) 0.3967(4) 0.0458(13) Uani 1 1 d . . . . .
N3 N 0.1554(6) 0.7377(7) 0.3941(4) 0.0448(11) Uani 1 1 d . . . . .
H3 H 0.0928 0.8233 0.4286 0.054 Uiso 1 1 calc R U . . .
C4 C 0.2773(6) 0.8029(8) 0.3306(4) 0.0381(10) Uani 1 1 d . . . . .
C5 C 0.3498(6) 0.6008(7) 0.2801(4) 0.0372(10) Uani 1 1 d . . . . .
O1 O 0.0464(6) 0.4129(7) 0.4500(4) 0.0677(12) Uani 1 1 d . . . . .
O2 O 0.3264(6) 0.9858(5) 0.3190(4) 0.0558(11) Uani 1 1 d . . . . .
C6 C 0.5683(7) 0.5879(11) 0.3408(5) 0.0572(15) Uani 1 1 d . . . . .
H6A H 0.6016 0.6046 0.4336 0.086 Uiso 1 1 calc R U . . .
H6B H 0.6272 0.7004 0.3058 0.086 Uiso 1 1 calc R U . . .
H6C H 0.6126 0.4508 0.3211 0.086 Uiso 1 1 calc R U . . .
C7 C 0.2939(5) 0.5992(9) 0.1316(4) 0.0373(10) Uani 1 1 d . . . . .
C8 C 0.3390(7) 0.7752(9) 0.0670(5) 0.0499(12) Uani 1 1 d . . . . .
H8 H 0.3999 0.8946 0.1137 0.060 Uiso 1 1 calc R U . . .
C9 C 0.2923(8) 0.7710(12) -0.0672(5) 0.0636(16) Uani 1 1 d . . . . .
H9 H 0.3231 0.8887 -0.1100 0.076 Uiso 1 1 calc R U . . .
C10 C 0.2018(8) 0.5978(14) -0.1389(5) 0.0650(16) Uani 1 1 d . . . . .
H10 H 0.1709 0.5980 -0.2292 0.078 Uiso 1 1 calc R U . . .
C11 C 0.1579(8) 0.4250(13) -0.0755(5) 0.0655(17) Uani 1 1 d . . . . .
H11 H 0.0988 0.3052 -0.1228 0.079 Uiso 1 1 calc R U . . .
C12 C 0.2010(7) 0.4272(9) 0.0590(4) 0.0486(12) Uani 1 1 d . . . . .
H12 H 0.1665 0.3105 0.1007 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
N1 C2 1.320(6) . ?
N1 C5 1.446(6) . ?
N1 H1 0.8600 . ?
C2 O1 1.217(6) . ?
C2 N3 1.401(7) . ?
N3 C4 1.349(6) . ?
N3 H3 0.8600 . ?
C4 O2 1.211(6) . ?
C4 C5 1.530(6) . ?
C5 C7 1.527(5) . ?
C5 C6 1.535(6) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C12 1.375(7) . ?
C7 C8 1.392(7) . ?
C8 C9 1.381(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.372(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.365(11) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(7) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

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
C2 N1 C5 113.8(4) . . ?
C2 N1 H1 123.1 . . ?
C5 N1 H1 123.1 . . ?
O1 C2 N1 128.0(5) . . ?
O1 C2 N3 124.7(5) . . ?
N1 C2 N3 107.3(4) . . ?
C4 N3 C2 111.4(4) . . ?
C4 N3 H3 124.3 . . ?
C2 N3 H3 124.3 . . ?
O2 C4 N3 126.9(4) . . ?
O2 C4 C5 125.9(4) . . ?
N3 C4 C5 107.2(4) . . ?
N1 C5 C7 113.6(4) . . ?
N1 C5 C4 100.3(3) . . ?
C7 C5 C4 111.7(4) . . ?
N1 C5 C6 111.2(4) . . ?
C7 C5 C6 110.6(3) . . ?
C4 C5 C6 108.9(4) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C7 C8 118.6(4) . . ?
C12 C7 C5 121.8(4) . . ?
C8 C7 C5 119.5(4) . . ?
C9 C8 C7 119.4(5) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C10 C9 C8 121.7(6) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C11 C10 C9 118.9(5) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C10 C11 C12 120.3(6) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C7 C12 C11 121.0(5) . . ?
C7 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?

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 C2 O1 179.5(5) . . . . ?
C5 N1 C2 N3 -0.6(6) . . . . ?
O1 C2 N3 C4 178.6(4) . . . . ?
N1 C2 N3 C4 -1.3(6) . . . . ?
C2 N3 C4 O2 -175.2(5) . . . . ?
C2 N3 C4 C5 2.5(5) . . . . ?
C2 N1 C5 C7 -117.4(5) . . . . ?
C2 N1 C5 C4 1.9(5) . . . . ?
C2 N1 C5 C6 117.0(5) . . . . ?
O2 C4 C5 N1 175.1(5) . . . . ?
N3 C4 C5 N1 -2.6(4) . . . . ?
O2 C4 C5 C7 -64.2(5) . . . . ?
N3 C4 C5 C7 118.1(4) . . . . ?
O2 C4 C5 C6 58.3(6) . . . . ?
N3 C4 C5 C6 -119.3(4) . . . . ?
N1 C5 C7 C12 -14.9(6) . . . . ?
C4 C5 C7 C12 -127.5(4) . . . . ?
C6 C5 C7 C12 111.0(5) . . . . ?
N1 C5 C7 C8 165.7(4) . . . . ?
C4 C5 C7 C8 53.0(5) . . . . ?
C6 C5 C7 C8 -68.5(6) . . . . ?
C12 C7 C8 C9 -1.1(7) . . . . ?
C5 C7 C8 C9 178.4(4) . . . . ?
C7 C8 C9 C10 0.2(8) . . . . ?
C8 C9 C10 C11 -0.3(9) . . . . ?
C9 C10 C11 C12 1.3(9) . . . . ?
C8 C7 C12 C11 2.0(7) . . . . ?
C5 C7 C12 C11 -177.5(5) . . . . ?
C10 C11 C12 C7 -2.1(8) . . . . ?

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
N1 H1 O2 0.86 2.00 2.860(5) 173.8 1_545
N3 H3 O1 0.86 1.98 2.788(5) 156.6 2_556

_refine_diff_density_max         0.269
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_Ni_2
_database_code_depnum_ccdc_archive 'CCDC 836483'
_audit_update_record             
;
2018-03-13 deposited with the CCDC.
2018-04-26 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 N6 Ni O6, 1.26(H2 O)'
_chemical_formula_sum            'C20 H30.52 N6 Ni O7.26'
_chemical_formula_weight         529.98

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'
Ni Ni 0.3393 1.1124 '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/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.3679(10)
_cell_length_b                   6.4569(7)
_cell_length_c                   18.3125(15)
_cell_angle_alpha                90
_cell_angle_beta                 98.023(7)
_cell_angle_gamma                90
_cell_volume                     1213.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1918
_cell_measurement_theta_min      3.20
_cell_measurement_theta_max      27.10

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_F_000             557
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.852
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.837
_exptl_absorpt_correction_T_max  0.906
_exptl_absorpt_process_details   'CrysAlis 1.171.32.6'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'KUMA KM-4 with area CCD detector'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean '1024x1024 with blocks 2x2, 33.133pixel/mm'
_diffrn_reflns_number            15944
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.198
_diffrn_reflns_theta_max         27.097
_diffrn_reflns_theta_full        25.242
_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             2684
_reflns_number_gt                1918
_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       'CrysAlis 1.171.32.6'
_computing_cell_refinement       'CrysAlis 1.171.32.6'
_computing_data_reduction        'CrysAlis 1.171.32.6'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0902P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2684
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_ref         0.1533
_refine_ls_wR_factor_gt          0.1396
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001

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 0.0000 0.0000 0.0352(2) Uani 1 2 d S . P . .
N1 N 0.1203(2) 0.1497(4) 0.05827(14) 0.0456(7) Uani 1 1 d . . . . .
H1 H 0.0376 0.1289 0.0538 0.055 Uiso 1 1 calc R U . . .
C2 C 0.2009(3) 0.0535(5) 0.01721(15) 0.0353(7) Uani 1 1 d . . . . .
O2 O 0.16524(19) -0.0708(4) -0.03238(11) 0.0424(5) Uani 1 1 d . . . . .
N3 N 0.3292(2) 0.1182(4) 0.03809(12) 0.0356(6) Uani 1 1 d . . . . .
C4 C 0.3291(3) 0.2538(5) 0.09264(18) 0.0430(7) Uani 1 1 d . . . . .
O4 O 0.4257(2) 0.3440(4) 0.12665(14) 0.0634(7) Uani 1 1 d . . . . .
C5 C 0.1896(3) 0.2916(5) 0.11044(18) 0.0431(7) Uani 1 1 d . . . . .
C11 C 0.1530(4) 0.5152(5) 0.0923(3) 0.0640(11) Uani 1 1 d . . . . .
H11A H 0.1665 0.5450 0.0425 0.096 Uiso 1 1 calc R U . . .
H11B H 0.2063 0.6053 0.1256 0.096 Uiso 1 1 calc R U . . .
H11C H 0.0630 0.5368 0.0973 0.096 Uiso 1 1 calc R U . . .
C21 C 0.1813(3) 0.2263(5) 0.18977(18) 0.0453(8) Uani 1 1 d . . . . .
C22 C 0.1321(3) 0.3550(7) 0.24024(19) 0.0580(10) Uani 1 1 d . . . . .
H22 H 0.1030 0.4874 0.2263 0.070 Uiso 1 1 calc R U . . .
C23 C 0.1267(3) 0.2854(8) 0.3111(2) 0.0747(14) Uani 1 1 d . . . . .
H23 H 0.0919 0.3711 0.3442 0.090 Uiso 1 1 calc R U . . .
C24 C 0.1711(4) 0.0948(10) 0.3336(2) 0.0752(13) Uani 1 1 d . . . . .
H24 H 0.1682 0.0513 0.3818 0.090 Uiso 1 1 calc R U . . .
C25 C 0.2197(4) -0.0312(7) 0.2849(2) 0.0719(12) Uani 1 1 d . . . . .
H25 H 0.2498 -0.1622 0.3000 0.086 Uiso 1 1 calc R U . . .
C26 C 0.2253(4) 0.0304(5) 0.2140(2) 0.0570(10) Uani 1 1 d . . . . .
H26 H 0.2588 -0.0592 0.1816 0.068 Uiso 1 1 calc R U . . .
N1A N 0.5509(3) -0.1429(7) 0.10223(17) 0.0841(12) Uani 1 1 d . . . . .
H1A1 H 0.5710 -0.0468 0.1367 0.101 Uiso 1 1 calc R U . . .
H2A1 H 0.6192 -0.2252 0.1004 0.101 Uiso 1 1 calc R U . . .
H3A1 H 0.4840 -0.2178 0.1131 0.101 Uiso 1 1 calc R U . . .
O1W O 0.6028(2) 0.2725(4) 0.03401(17) 0.0746(9) Uani 1 1 d . . . . .
H1W1 H 0.5725 0.3010 0.0781 0.090 Uiso 1 1 d . U . . .
H2W1 H 0.6891 0.2451 0.0492 0.090 Uiso 1 1 d . U . . .
O2W O 0.5697(5) 0.1036(12) 0.2521(4) 0.122(4) Uani 0.631(12) 1 d . . P . .
H1W2 H 0.5495 0.0447 0.2946 0.183 Uiso 0.6313 1 d . U P . .
H2W2 H 0.4955 0.1426 0.2239 0.183 Uiso 0.6313 1 d . 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 N1A 2.088(3) 3_655 ?
Ni1 N1A 2.088(3) . ?
Ni1 O1W 2.106(3) . ?
Ni1 O1W 2.106(3) 3_655 ?
Ni1 N3 2.133(2) . ?
Ni1 N3 2.133(2) 3_655 ?
N1 C2 1.351(4) . ?
N1 C5 1.441(4) . ?
N1 H1 0.8600 . ?
C2 O2 1.229(4) . ?
C2 N3 1.396(3) . ?
N3 C4 1.329(4) . ?
C4 O4 1.247(4) . ?
C4 C5 1.546(4) . ?
C5 C11 1.518(4) . ?
C5 C21 1.527(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C21 C22 1.391(4) . ?
C21 C26 1.396(5) . ?
C22 C23 1.382(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.357(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.356(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.366(6) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
N1A H1A1 0.8900 . ?
N1A H2A1 0.8900 . ?
N1A H3A1 0.8900 . ?
O1W H1W1 0.9245 . ?
O1W H2W1 0.9163 . ?
O2W H1W2 0.9159 . ?
O2W H2W2 0.9005 . ?

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
N1A Ni1 N1A 180.00(9) 3_655 . ?
N1A Ni1 O1W 87.13(15) 3_655 . ?
N1A Ni1 O1W 92.87(15) . . ?
N1A Ni1 O1W 92.87(15) 3_655 3_655 ?
N1A Ni1 O1W 87.13(15) . 3_655 ?
O1W Ni1 O1W 180.0 . 3_655 ?
N1A Ni1 N3 91.02(11) 3_655 . ?
N1A Ni1 N3 88.98(11) . . ?
O1W Ni1 N3 90.77(9) . . ?
O1W Ni1 N3 89.23(9) 3_655 . ?
N1A Ni1 N3 88.98(11) 3_655 3_655 ?
N1A Ni1 N3 91.02(11) . 3_655 ?
O1W Ni1 N3 89.23(9) . 3_655 ?
O1W Ni1 N3 90.77(9) 3_655 3_655 ?
N3 Ni1 N3 180.00(5) . 3_655 ?
C2 N1 C5 111.8(2) . . ?
C2 N1 H1 124.1 . . ?
C5 N1 H1 124.1 . . ?
O2 C2 N1 124.4(3) . . ?
O2 C2 N3 125.1(2) . . ?
N1 C2 N3 110.5(3) . . ?
C4 N3 C2 107.6(2) . . ?
C4 N3 Ni1 124.71(19) . . ?
C2 N3 Ni1 127.32(18) . . ?
O4 C4 N3 126.8(3) . . ?
O4 C4 C5 122.1(3) . . ?
N3 C4 C5 111.2(3) . . ?
N1 C5 C11 111.9(3) . . ?
N1 C5 C21 111.5(3) . . ?
C11 C5 C21 115.2(3) . . ?
N1 C5 C4 98.9(2) . . ?
C11 C5 C4 108.4(3) . . ?
C21 C5 C4 109.6(3) . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C22 C21 C26 117.6(3) . . ?
C22 C21 C5 122.8(3) . . ?
C26 C21 C5 119.6(3) . . ?
C23 C22 C21 119.7(4) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C24 C23 C22 121.6(4) . . ?
C24 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C25 C24 C23 119.0(4) . . ?
C25 C24 H24 120.5 . . ?
C23 C24 H24 120.5 . . ?
C24 C25 C26 121.3(4) . . ?
C24 C25 H25 119.3 . . ?
C26 C25 H25 119.3 . . ?
C25 C26 C21 120.7(4) . . ?
C25 C26 H26 119.7 . . ?
C21 C26 H26 119.7 . . ?
Ni1 N1A H1A1 109.5 . . ?
Ni1 N1A H2A1 109.5 . . ?
H1A1 N1A H2A1 109.5 . . ?
Ni1 N1A H3A1 109.5 . . ?
H1A1 N1A H3A1 109.5 . . ?
H2A1 N1A H3A1 109.5 . . ?
Ni1 O1W H1W1 101.8 . . ?
Ni1 O1W H2W1 111.2 . . ?
H1W1 O1W H2W1 102.1 . . ?
H1W2 O2W H2W2 109.0 . . ?

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 C2 O2 -178.1(3) . . . . ?
C5 N1 C2 N3 0.7(4) . . . . ?
O2 C2 N3 C4 179.3(3) . . . . ?
N1 C2 N3 C4 0.5(3) . . . . ?
O2 C2 N3 Ni1 -7.3(4) . . . . ?
N1 C2 N3 Ni1 173.89(19) . . . . ?
C2 N3 C4 O4 178.9(3) . . . . ?
Ni1 N3 C4 O4 5.3(5) . . . . ?
C2 N3 C4 C5 -1.4(3) . . . . ?
Ni1 N3 C4 C5 -175.04(19) . . . . ?
C2 N1 C5 C11 112.7(3) . . . . ?
C2 N1 C5 C21 -116.7(3) . . . . ?
C2 N1 C5 C4 -1.4(3) . . . . ?
O4 C4 C5 N1 -178.6(3) . . . . ?
N3 C4 C5 N1 1.7(3) . . . . ?
O4 C4 C5 C11 64.7(4) . . . . ?
N3 C4 C5 C11 -115.0(3) . . . . ?
O4 C4 C5 C21 -61.9(4) . . . . ?
N3 C4 C5 C21 118.4(3) . . . . ?
N1 C5 C21 C22 -123.0(3) . . . . ?
C11 C5 C21 C22 5.9(4) . . . . ?
C4 C5 C21 C22 128.5(3) . . . . ?
N1 C5 C21 C26 57.5(4) . . . . ?
C11 C5 C21 C26 -173.6(3) . . . . ?
C4 C5 C21 C26 -51.0(4) . . . . ?
C26 C21 C22 C23 -0.9(5) . . . . ?
C5 C21 C22 C23 179.6(3) . . . . ?
C21 C22 C23 C24 1.5(6) . . . . ?
C22 C23 C24 C25 -1.2(6) . . . . ?
C23 C24 C25 C26 0.3(6) . . . . ?
C24 C25 C26 C21 0.2(6) . . . . ?
C22 C21 C26 C25 0.1(5) . . . . ?
C5 C21 C26 C25 179.6(3) . . . . ?

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
N1 H1 O2 0.86 2.12 2.976(3) 174.7 3
N1A H1A1 O2W 0.89 2.33 3.156(9) 154.9 .
O1W H1W1 O4 0.92 1.89 2.708(3) 146.7 .
O1W H2W1 O2 0.92 1.94 2.739(3) 144.2 3_655
O2W H1W2 O4 0.92 1.93 2.776(6) 153.0 2_645
O2W H2W2 O4 0.90 2.24 2.994(6) 140.7 .

_refine_diff_density_max         0.839
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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_Ni_1
_database_code_depnum_ccdc_archive 'CCDC 836482'
_audit_update_record             
;
2018-03-13 deposited with the CCDC.
2018-04-26 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 N6 Ni O6, 1.23(N H3)'
_chemical_formula_sum            'C20 H31.66 N7.23 Ni O6'
_chemical_formula_weight         528.11

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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   6.7306(12)
_cell_length_b                   8.9921(13)
_cell_length_c                   10.4338(15)
_cell_angle_alpha                95.898(12)
_cell_angle_beta                 91.502(13)
_cell_angle_gamma                99.545(14)
_cell_volume                     618.84(17)
_cell_formula_units_Z            1
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2107
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      26.73

_exptl_crystal_description       prism
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_F_000             278
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    0.833
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.824
_exptl_absorpt_correction_T_max  0.899
_exptl_absorpt_process_details   'CrysAlis 1.171.32.6'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'KUMA KM-4 with area CCD detector'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean '1024x1024 with blocks 2x2, 33.133pixel/mm'
_diffrn_reflns_number            7749
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.072
_diffrn_reflns_theta_max         26.731
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2611
_reflns_number_gt                2107
_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       'CrysAlis 1.171.32.6'
_computing_cell_refinement       'CrysAlis 1.171.32.6'
_computing_data_reduction        'CrysAlis 1.171.32.6'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0718P)²+0.3075P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2611
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.1507
_refine_ls_wR_factor_gt          0.1394
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_restrained_S_all      1.114
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001

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 0.0000 0.0000 0.5000 0.0434(2) Uani 1 2 d S . P . .
N1 N -0.1839(4) -0.1072(3) 0.8841(2) 0.0493(7) Uani 1 1 d . . . . .
H1 H -0.1624 -0.0965 0.9664 0.059 Uiso 1 1 calc R U . . .
C2 C -0.0676(5) -0.0284(3) 0.8018(2) 0.0385(6) Uani 1 1 d . . . . .
O2 O 0.0816(3) 0.0686(2) 0.83610(19) 0.0482(5) Uani 1 1 d . . . . .
N3 N -0.1400(4) -0.0709(3) 0.6748(2) 0.0404(6) Uani 1 1 d . . . . .
C4 C -0.3047(5) -0.1760(3) 0.6773(3) 0.0431(7) Uani 1 1 d . . . . .
O4 O -0.4143(4) -0.2384(3) 0.5843(2) 0.0621(7) Uani 1 1 d . . . . .
C5 C -0.3489(5) -0.2117(3) 0.8166(3) 0.0440(7) Uani 1 1 d . . . . .
C11 C -0.5513(6) -0.1677(4) 0.8528(4) 0.0596(9) Uani 1 1 d . . . . .
H11A H -0.5849 -0.1983 0.9361 0.089 Uiso 1 1 calc R U . . .
H11B H -0.6540 -0.2173 0.7898 0.089 Uiso 1 1 calc R U . . .
H11C H -0.5424 -0.0597 0.8552 0.089 Uiso 1 1 calc R U . . .
C21 C -0.3354(5) -0.3768(3) 0.8281(3) 0.0430(7) Uani 1 1 d . . . . .
C22 C -0.5040(6) -0.4876(4) 0.8165(4) 0.0681(10) Uani 1 1 d . . . . .
H22 H -0.6306 -0.4610 0.8053 0.082 Uiso 1 1 calc R U . . .
C23 C -0.4872(8) -0.6389(5) 0.8212(5) 0.0842(14) Uani 1 1 d . . . . .
H23 H -0.6030 -0.7123 0.8134 0.101 Uiso 1 1 calc R U . . .
C24 C -0.3041(8) -0.6812(4) 0.8369(4) 0.0710(12) Uani 1 1 d . . . . .
H24 H -0.2935 -0.7829 0.8381 0.085 Uiso 1 1 calc R U . . .
C25 C -0.1387(7) -0.5733(5) 0.8506(4) 0.0744(11) Uani 1 1 d . . . . .
H25 H -0.0130 -0.6008 0.8633 0.089 Uiso 1 1 calc R U . . .
C26 C -0.1520(6) -0.4219(4) 0.8461(4) 0.0638(9) Uani 1 1 d . . . . .
H26 H -0.0351 -0.3496 0.8554 0.077 Uiso 1 1 calc R U . . .
N1A N -0.0047(8) -0.2290(4) 0.4333(4) 0.1085(18) Uani 1 1 d . . . . .
H1A1 H 0.1069 -0.2582 0.4620 0.130 Uiso 1 1 calc R U . . .
H2A1 H -0.0108 -0.2404 0.3475 0.130 Uiso 1 1 calc R U . . .
H3A1 H -0.1121 -0.2855 0.4622 0.130 Uiso 1 1 calc R U . . .
O1W O -0.2833(5) -0.0174(5) 0.4084(3) 0.1015(12) Uani 1 1 d . . . . .
H1W1 H -0.3700 -0.0920 0.4419 0.122 Uiso 1 1 d . U . . .
H2W1 H -0.2801 -0.0479 0.3230 0.122 Uiso 1 1 d . U . . .
N2A N 0.2545(10) 0.5454(8) 0.5131(7) 0.088(3) Uani 0.613(14) 1 d . . P . .
H1N2 H 0.3307 0.6280 0.5438 0.131 Uiso 0.6128 1 d . U P . .
H2N2 H 0.3157 0.4719 0.5275 0.131 Uiso 0.6128 1 d . U P . .
H3N2 H 0.2268 0.5442 0.4340 0.131 Uiso 0.6128 1 d . 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 O1W 2.085(3) . ?
Ni1 O1W 2.085(3) 2_556 ?
Ni1 N1A 2.100(3) . ?
Ni1 N1A 2.100(3) 2_556 ?
Ni1 N3 2.179(2) . ?
Ni1 N3 2.179(2) 2_556 ?
N1 C2 1.353(3) . ?
N1 C5 1.445(4) . ?
N1 H1 0.8600 . ?
C2 O2 1.235(4) . ?
C2 N3 1.393(4) . ?
N3 C4 1.335(4) . ?
C4 O4 1.230(4) . ?
C4 C5 1.546(4) . ?
C5 C21 1.519(4) . ?
C5 C11 1.526(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C21 C22 1.374(5) . ?
C21 C26 1.376(5) . ?
C22 C23 1.389(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.360(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.344(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.384(6) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
N1A H1A1 0.8900 . ?
N1A H2A1 0.8900 . ?
N1A H3A1 0.8900 . ?
O1W H1W1 0.9173 . ?
O1W H2W1 0.9070 . ?
N2A H1N2 0.8564 . ?
N2A H2N2 0.8585 . ?
N2A H3N2 0.8394 . ?

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
O1W Ni1 O1W 180.0(2) . 2_556 ?
O1W Ni1 N1A 88.1(2) . . ?
O1W Ni1 N1A 91.9(2) 2_556 . ?
O1W Ni1 N1A 91.9(2) . 2_556 ?
O1W Ni1 N1A 88.1(2) 2_556 2_556 ?
N1A Ni1 N1A 180.0 . 2_556 ?
O1W Ni1 N3 90.48(11) . . ?
O1W Ni1 N3 89.52(11) 2_556 . ?
N1A Ni1 N3 89.07(11) . . ?
N1A Ni1 N3 90.93(11) 2_556 . ?
O1W Ni1 N3 89.52(11) . 2_556 ?
O1W Ni1 N3 90.48(11) 2_556 2_556 ?
N1A Ni1 N3 90.93(11) . 2_556 ?
N1A Ni1 N3 89.08(11) 2_556 2_556 ?
N3 Ni1 N3 180.0 . 2_556 ?
C2 N1 C5 111.6(2) . . ?
C2 N1 H1 124.2 . . ?
C5 N1 H1 124.2 . . ?
O2 C2 N1 123.9(3) . . ?
O2 C2 N3 125.2(2) . . ?
N1 C2 N3 110.9(3) . . ?
C4 N3 C2 107.3(2) . . ?
C4 N3 Ni1 124.88(18) . . ?
C2 N3 Ni1 127.53(19) . . ?
O4 C4 N3 126.8(3) . . ?
O4 C4 C5 121.9(3) . . ?
N3 C4 C5 111.3(2) . . ?
N1 C5 C21 113.0(3) . . ?
N1 C5 C11 110.9(3) . . ?
C21 C5 C11 114.2(3) . . ?
N1 C5 C4 98.9(2) . . ?
C21 C5 C4 109.3(2) . . ?
C11 C5 C4 109.4(3) . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C22 C21 C26 117.3(3) . . ?
C22 C21 C5 121.6(3) . . ?
C26 C21 C5 121.0(3) . . ?
C21 C22 C23 120.7(4) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C24 C23 C22 121.0(4) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C25 C24 C23 118.7(4) . . ?
C25 C24 H24 120.7 . . ?
C23 C24 H24 120.7 . . ?
C24 C25 C26 121.2(4) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 H25 119.4 . . ?
C21 C26 C25 121.0(4) . . ?
C21 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
Ni1 N1A H1A1 109.5 . . ?
Ni1 N1A H2A1 109.5 . . ?
H1A1 N1A H2A1 109.5 . . ?
Ni1 N1A H3A1 109.5 . . ?
H1A1 N1A H3A1 109.5 . . ?
H2A1 N1A H3A1 109.5 . . ?
Ni1 O1W H1W1 108.2 . . ?
Ni1 O1W H2W1 111.1 . . ?
H1W1 O1W H2W1 106.1 . . ?
H1N2 N2A H2N2 107.5 . . ?
H1N2 N2A H3N2 111.9 . . ?
H2N2 N2A H3N2 111.1 . . ?

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 C2 O2 179.4(3) . . . . ?
C5 N1 C2 N3 -0.2(4) . . . . ?
O2 C2 N3 C4 -178.8(3) . . . . ?
N1 C2 N3 C4 0.8(3) . . . . ?
O2 C2 N3 Ni1 6.9(4) . . . . ?
N1 C2 N3 Ni1 -173.5(2) . . . . ?
C2 N3 C4 O4 177.9(3) . . . . ?
Ni1 N3 C4 O4 -7.6(5) . . . . ?
C2 N3 C4 C5 -1.0(3) . . . . ?
Ni1 N3 C4 C5 173.48(19) . . . . ?
C2 N1 C5 C21 115.1(3) . . . . ?
C2 N1 C5 C11 -115.1(3) . . . . ?
C2 N1 C5 C4 -0.4(3) . . . . ?
O4 C4 C5 N1 -178.1(3) . . . . ?
N3 C4 C5 N1 0.9(3) . . . . ?
O4 C4 C5 C21 63.6(4) . . . . ?
N3 C4 C5 C21 -117.5(3) . . . . ?
O4 C4 C5 C11 -62.2(4) . . . . ?
N3 C4 C5 C11 116.8(3) . . . . ?
N1 C5 C21 C22 154.6(3) . . . . ?
C11 C5 C21 C22 26.5(4) . . . . ?
C4 C5 C21 C22 -96.4(4) . . . . ?
N1 C5 C21 C26 -27.8(4) . . . . ?
C11 C5 C21 C26 -155.8(3) . . . . ?
C4 C5 C21 C26 81.3(4) . . . . ?
C26 C21 C22 C23 -0.9(6) . . . . ?
C5 C21 C22 C23 176.9(4) . . . . ?
C21 C22 C23 C24 -0.2(7) . . . . ?
C22 C23 C24 C25 1.4(7) . . . . ?
C23 C24 C25 C26 -1.4(7) . . . . ?
C22 C21 C26 C25 0.8(6) . . . . ?
C5 C21 C26 C25 -177.0(3) . . . . ?
C24 C25 C26 C21 0.3(6) . . . . ?

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
N1 H1 O2 0.86 2.10 2.953(3) 174.7 2_557
N1A H1A1 N2A 0.89 2.27 3.049(9) 146.5 1_545
N1A H3A1 N2A 0.89 2.42 3.166(8) 142.0 2_556
N1A H3A1 O4 0.89 2.50 3.205(5) 136.4 .
O1W H1W1 O4 0.92 2.08 2.889(4) 146.5 .
O1W H2W1 O2 0.91 2.17 2.951(4) 143.8 2_556
N2A H1N2 O4 0.86 1.93 2.736(6) 155.1 1_665
N2A H2N2 O4 0.86 2.49 3.206(8) 141.1 2_556

_refine_diff_density_max         0.451
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.072

