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

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

data_3
_database_code_depnum_ccdc_archive 'CCDC 1530062'
_audit_update_record             
;
2017-01-29 deposited with the CCDC.
2017-07-10 downloaded from the CCDC.
;
_audit_creation_date             2017-01-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H22 N8 Ni O2'
_chemical_formula_sum            'C12 H22 N8 Ni O2'
_chemical_formula_weight         369.08
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Ni N4 C12 H12 O2'
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 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   6.5790(3)
_cell_length_b                   14.3346(7)
_cell_length_c                   8.3734(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.976(5)
_cell_angle_gamma                90
_cell_volume                     789.21(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5751
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.1828
_cell_measurement_theta_min      2.8128
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.253
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72055
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13141
_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         27.499
_diffrn_reflns_theta_min         2.818
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -53.00   -4.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.4031  -77.0000  -30.0000 49

#__ type_ start__ end____ width___ exp.time_
  2 omega  -72.00  -46.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.4031  178.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -20.00   66.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968  -99.0000  -90.0000 86

#__ type_ start__ end____ width___ exp.time_
  4 omega   13.00   97.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968   19.0000    0.0000 84

#__ type_ start__ end____ width___ exp.time_
  5 omega    3.00   89.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968   77.0000 -180.0000 86

#__ type_ start__ end____ width___ exp.time_
  6 omega  -44.00   57.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968  -77.0000   60.0000 101

#__ type_ start__ end____ width___ exp.time_
  7 omega  -42.00   57.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968  -77.0000  -30.0000 99

#__ type_ start__ end____ width___ exp.time_
  8 omega   35.00  102.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968  178.0000  -90.0000 67

#__ type_ start__ end____ width___ exp.time_
  9 omega   -2.00   82.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968   77.0000  -90.0000 84

#__ type_ start__ end____ width___ exp.time_
 10 omega   -4.00   88.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968   77.0000   90.0000 92

#__ type_ start__ end____ width___ exp.time_
 11 omega   19.00   99.00   1.0000   22.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968   38.0000   60.0000 80
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0800594000
_diffrn_orient_matrix_UB_12      -0.0261058000
_diffrn_orient_matrix_UB_13      -0.0327524000
_diffrn_orient_matrix_UB_21      0.0234606000
_diffrn_orient_matrix_UB_22      -0.0194311000
_diffrn_orient_matrix_UB_23      0.0764234000
_diffrn_orient_matrix_UB_31      -0.0683693000
_diffrn_orient_matrix_UB_32      -0.0372332000
_diffrn_orient_matrix_UB_33      -0.0167887000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1688
_reflns_number_total             1820
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     106
_refine_ls_number_reflns         1820
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0252
_refine_ls_R_factor_gt           0.0229
_refine_ls_restrained_S_all      1.061
_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)+(0.0272P)²+0.4648P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0579
_refine_ls_wR_factor_ref         0.0594
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.5000 0.5000 0.5000 0.01135(8) Uani 1 2 d S T P . .
O1 O 0.87175(14) 0.44615(7) 0.38730(12) 0.0180(2) Uani 1 1 d . . . . .
N1 N 0.68968(17) 0.42393(8) 0.40198(13) 0.0132(2) Uani 1 1 d . . . . .
N2 N 0.32767(17) 0.40438(8) 0.43553(14) 0.0143(2) Uani 1 1 d . . . . .
H2 H 0.1958 0.4053 0.4496 0.017 Uiso 1 1 calc R . . . .
N4 N 0.33661(17) 0.25747(8) 0.30482(14) 0.0149(2) Uani 1 1 d . . . . .
N3 N 0.63242(17) 0.34223(8) 0.35006(13) 0.0138(2) Uani 1 1 d . . . . .
C1 C 0.4207(2) 0.33499(9) 0.36674(15) 0.0128(3) Uani 1 1 d . . . . .
C6 C 0.4559(2) 0.17465(9) 0.26419(17) 0.0165(3) Uani 1 1 d . . . . .
H6A H 0.6017 0.1913 0.2608 0.020 Uiso 1 1 calc R . . . .
H6B H 0.4113 0.1514 0.1573 0.020 Uiso 1 1 calc R . . . .
C2 C 0.1176(2) 0.23850(10) 0.31089(17) 0.0165(3) Uani 1 1 d . . . . .
H2A H 0.0658 0.2161 0.2053 0.020 Uiso 1 1 calc R . . . .
H2B H 0.0443 0.2966 0.3367 0.020 Uiso 1 1 calc R . . . .
C3 C 0.0796(2) 0.16497(10) 0.43760(17) 0.0189(3) Uani 1 1 d . . . . .
H3A H -0.0672 0.1497 0.4369 0.023 Uiso 1 1 calc R . . . .
H3B H 0.1188 0.1901 0.5444 0.023 Uiso 1 1 calc R . . . .
C5 C 0.4267(2) 0.09868(10) 0.38861(18) 0.0194(3) Uani 1 1 d . . . . .
H5A H 0.4866 0.1194 0.4928 0.023 Uiso 1 1 calc R . . . .
H5B H 0.4990 0.0415 0.3563 0.023 Uiso 1 1 calc R . . . .
C4 C 0.2014(2) 0.07658(10) 0.40680(19) 0.0216(3) Uani 1 1 d . . . . .
H4A H 0.1471 0.0460 0.3083 0.026 Uiso 1 1 calc R . . . .
H4B H 0.1861 0.0326 0.4968 0.026 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ni1 0.00897(13) 0.01063(13) 0.01443(13) -0.00066(8) 0.00010(9) 0.00041(8)
O1 0.0094(4) 0.0185(5) 0.0260(5) -0.0019(4) 0.0015(4) -0.0010(4)
N1 0.0108(5) 0.0143(5) 0.0144(5) 0.0012(4) -0.0011(4) 0.0001(4)
N2 0.0099(5) 0.0144(5) 0.0185(6) -0.0013(4) 0.0011(4) 0.0008(4)
N4 0.0122(5) 0.0124(5) 0.0200(6) -0.0014(4) 0.0012(4) -0.0003(4)
N3 0.0113(5) 0.0134(5) 0.0166(5) -0.0011(4) 0.0007(4) 0.0000(4)
C1 0.0128(6) 0.0128(6) 0.0127(6) 0.0025(5) -0.0007(5) 0.0003(5)
C6 0.0172(6) 0.0134(6) 0.0191(7) -0.0037(5) 0.0037(5) 0.0006(5)
C2 0.0121(6) 0.0150(6) 0.0222(7) -0.0020(5) -0.0008(5) -0.0012(5)
C3 0.0159(7) 0.0193(7) 0.0217(7) -0.0020(5) 0.0043(5) -0.0027(5)
C5 0.0201(7) 0.0131(6) 0.0252(7) 0.0003(5) 0.0033(6) 0.0021(5)
C4 0.0222(7) 0.0147(7) 0.0281(8) 0.0015(6) 0.0044(6) -0.0016(6)

_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 1.8683(11) . ?
Ni1 N1 1.8684(11) 3_666 ?
Ni1 N2 1.8475(11) 3_666 ?
Ni1 N2 1.8475(11) . ?
O1 N1 1.2496(15) . ?
N1 N3 1.3004(16) . ?
N2 C1 1.3114(17) . ?
N4 C1 1.3378(17) . ?
N4 C6 1.4695(17) . ?
N4 C2 1.4686(17) . ?
N3 C1 1.4087(17) . ?
C6 C5 1.5239(19) . ?
C2 C3 1.5224(19) . ?
C3 C4 1.526(2) . ?
C5 C4 1.528(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 . 3_666 ?
N2 Ni1 N1 98.56(5) . 3_666 ?
N2 Ni1 N1 81.44(5) . . ?
N2 Ni1 N1 98.56(5) 3_666 . ?
N2 Ni1 N1 81.44(5) 3_666 3_666 ?
N2 Ni1 N2 180.0 3_666 . ?
O1 N1 Ni1 123.46(9) . . ?
O1 N1 N3 117.67(11) . . ?
N3 N1 Ni1 118.84(9) . . ?
C1 N2 Ni1 113.59(9) . . ?
C1 N4 C6 122.95(11) . . ?
C1 N4 C2 122.23(11) . . ?
C2 N4 C6 113.00(11) . . ?
N1 N3 C1 108.01(11) . . ?
N2 C1 N4 127.40(12) . . ?
N2 C1 N3 117.75(12) . . ?
N4 C1 N3 114.82(11) . . ?
N4 C6 C5 109.77(11) . . ?
N4 C2 C3 109.73(11) . . ?
C2 C3 C4 110.92(12) . . ?
C6 C5 C4 111.21(12) . . ?
C3 C4 C5 111.20(12) . . ?

_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_4
_database_code_depnum_ccdc_archive 'CCDC 1530060'
_audit_update_record             
;
2017-01-29 deposited with the CCDC.
2017-07-10 downloaded from the CCDC.
;
_audit_creation_date             2017-01-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H18 N8 Ni O2'
_chemical_formula_sum            'C10 H18 N8 Ni O2'
_chemical_formula_weight         341.03
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Ni cl C25 H20 N4 S'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7068(10)
_cell_length_b                   6.7518(12)
_cell_length_c                   7.8797(10)
_cell_angle_alpha                75.399(13)
_cell_angle_beta                 81.175(12)
_cell_angle_gamma                81.118(14)
_cell_volume                     338.70(9)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1074
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.1820
_cell_measurement_theta_min      5.8320
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.262
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88160
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.672
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             178
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2391
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.923
_diffrn_reflns_theta_min         5.845
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -67.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3104   57.0000   90.0000 97

#__ type_ start__ end____ width___ exp.time_
  2 omega -108.00  -21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3104  -57.0000  -60.0000 87

#__ type_ start__ end____ width___ exp.time_
  3 omega -130.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.3104 -178.0000   90.0000 94

#__ type_ start__ end____ width___ exp.time_
  4 omega   67.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000   60.0000 40

#__ type_ start__ end____ width___ exp.time_
  5 omega   58.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000  120.0000 34

#__ type_ start__ end____ width___ exp.time_
  6 omega   46.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  150.0000 29

#__ type_ start__ end____ width___ exp.time_
  7 omega   47.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   30.0000 40

#__ type_ start__ end____ width___ exp.time_
  8 omega   54.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000  -60.0000 52

#__ type_ start__ end____ width___ exp.time_
  9 omega   66.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 10 omega   95.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega   48.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -120.0000 48

#__ type_ start__ end____ width___ exp.time_
 12 omega   94.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000  -60.0000 84

#__ type_ start__ end____ width___ exp.time_
 13 omega  146.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000    0.0000 30

#__ type_ start__ end____ width___ exp.time_
 14 omega  132.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   30.0000 44

#__ type_ start__ end____ width___ exp.time_
 15 omega  121.00  147.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   88.00  123.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   30.0000 35

#__ type_ start__ end____ width___ exp.time_
 17 omega   87.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 18 omega   40.00   94.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000    0.0000 54

#__ type_ start__ end____ width___ exp.time_
 19 omega   42.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000    0.0000 63

#__ type_ start__ end____ width___ exp.time_
 20 omega   40.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000 -180.0000 59

#__ type_ start__ end____ width___ exp.time_
 21 omega   49.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000 -180.0000 34

#__ type_ start__ end____ width___ exp.time_
 22 omega   43.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -180.0000 54

#__ type_ start__ end____ width___ exp.time_
 23 omega   81.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  150.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1651904000
_diffrn_orient_matrix_UB_12      -0.0853190000
_diffrn_orient_matrix_UB_13      -0.1307944000
_diffrn_orient_matrix_UB_21      -0.1187560000
_diffrn_orient_matrix_UB_22      -0.1834763000
_diffrn_orient_matrix_UB_23      0.0174007000
_diffrn_orient_matrix_UB_31      -0.1159625000
_diffrn_orient_matrix_UB_32      0.1244109000
_diffrn_orient_matrix_UB_33      -0.1549267000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1219
_reflns_number_total             1368
_reflns_odcompleteness_completeness 97.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     75.12
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.617
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1368
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0376
_refine_ls_restrained_S_all      1.080
_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)+(0.0470P)²+0.0773P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0991
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C2(H2A,H2B), C4(H4A,H4B), C3(H3A,H3B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.5000 0.5000 0.0000 0.01454(18) Uani 1 2 d S T P . .
O1 O 0.3422(3) 0.1280(2) 0.0884(3) 0.0267(4) Uani 1 1 d . . . . .
N3 N 0.1332(3) 0.3774(3) 0.1726(3) 0.0177(4) Uani 1 1 d . . . . .
N4 N -0.0322(3) 0.6751(3) 0.2490(3) 0.0163(4) Uani 1 1 d . . . . .
N2 N 0.2948(3) 0.6769(3) 0.0880(3) 0.0165(4) Uani 1 1 d . . . . .
C5 C -0.2085(3) 0.5678(3) 0.3407(3) 0.0180(4) Uani 1 1 d . . . . .
H5A H -0.1738 0.4667 0.4502 0.022 Uiso 1 1 calc R . . . .
H5B H -0.2583 0.4959 0.2634 0.022 Uiso 1 1 calc R . . . .
N1 N 0.3090(3) 0.3132(3) 0.0953(3) 0.0174(4) Uani 1 1 d . . . . .
C1 C 0.1339(3) 0.5871(3) 0.1673(3) 0.0150(4) Uani 1 1 d . . . . .
C2 C -0.0539(3) 0.8909(3) 0.2653(3) 0.0192(5) Uani 1 1 d . . . . .
H2A H -0.0768 0.9886 0.1511 0.023 Uiso 1 1 calc R . . . .
H2B H 0.0682 0.9203 0.3065 0.023 Uiso 1 1 calc R . . . .
C4 C -0.3657(4) 0.7438(4) 0.3821(4) 0.0270(5) Uani 1 1 d . . . . .
H4A H -0.4507 0.8009 0.2847 0.032 Uiso 1 1 calc R . . . .
H4B H -0.4550 0.6961 0.4928 0.032 Uiso 1 1 calc R . . . .
C3 C -0.2394(4) 0.9046(4) 0.4020(4) 0.0242(5) Uani 1 1 d . . . . .
H3A H -0.3164 1.0441 0.3778 0.029 Uiso 1 1 calc R . . . .
H3B H -0.1989 0.8722 0.5226 0.029 Uiso 1 1 calc R . . . .
H2 H 0.295(5) 0.795(5) 0.086(4) 0.028(8) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ni1 0.0101(3) 0.0143(3) 0.0176(3) -0.0033(2) 0.0027(2) -0.00195(19)
O1 0.0214(8) 0.0136(7) 0.0431(12) -0.0103(7) 0.0109(8) -0.0046(6)
N3 0.0131(8) 0.0175(9) 0.0212(10) -0.0042(7) 0.0031(7) -0.0030(7)
N4 0.0125(8) 0.0167(8) 0.0185(10) -0.0042(7) 0.0033(7) -0.0033(7)
N2 0.0118(8) 0.0149(9) 0.0216(11) -0.0044(7) 0.0022(7) -0.0014(7)
C5 0.0113(9) 0.0223(10) 0.0200(11) -0.0059(9) 0.0032(8) -0.0044(8)
N1 0.0145(8) 0.0166(9) 0.0195(10) -0.0040(7) 0.0026(7) -0.0017(7)
C1 0.0119(9) 0.0182(10) 0.0144(11) -0.0042(8) -0.0009(8) -0.0008(8)
C2 0.0176(10) 0.0161(10) 0.0227(12) -0.0068(9) 0.0035(9) -0.0006(8)
C4 0.0162(11) 0.0281(12) 0.0370(15) -0.0135(11) 0.0067(10) -0.0037(9)
C3 0.0205(11) 0.0241(11) 0.0268(14) -0.0085(10) 0.0056(10) -0.0032(9)

_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 N2 1.8492(19) 2_665 ?
Ni1 N2 1.8492(19) . ?
Ni1 N1 1.8767(19) 2_665 ?
Ni1 N1 1.8767(19) . ?
O1 N1 1.249(2) . ?
N3 N1 1.306(3) . ?
N3 C1 1.407(3) . ?
N4 C5 1.478(3) . ?
N4 C1 1.333(3) . ?
N4 C2 1.478(3) . ?
N2 C1 1.314(3) . ?
N2 H2 0.79(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C4 1.528(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.523(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C3 1.527(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Ni1 N2 180.00(9) 2_665 . ?
N2 Ni1 N1 98.60(8) 2_665 . ?
N2 Ni1 N1 81.39(8) 2_665 2_665 ?
N2 Ni1 N1 81.39(8) . . ?
N2 Ni1 N1 98.61(8) . 2_665 ?
N1 Ni1 N1 180.0 2_665 . ?
N1 N3 C1 107.28(18) . . ?
C5 N4 C2 112.55(18) . . ?
C1 N4 C5 124.64(18) . . ?
C1 N4 C2 122.73(19) . . ?
Ni1 N2 H2 128(2) . . ?
C1 N2 Ni1 113.25(15) . . ?
C1 N2 H2 118(2) . . ?
N4 C5 H5A 111.2 . . ?
N4 C5 H5B 111.2 . . ?
N4 C5 C4 102.87(18) . . ?
H5A C5 H5B 109.1 . . ?
C4 C5 H5A 111.2 . . ?
C4 C5 H5B 111.2 . . ?
O1 N1 Ni1 122.88(15) . . ?
O1 N1 N3 117.86(18) . . ?
N3 N1 Ni1 119.26(14) . . ?
N4 C1 N3 115.10(19) . . ?
N2 C1 N3 118.8(2) . . ?
N2 C1 N4 126.1(2) . . ?
N4 C2 H2A 111.1 . . ?
N4 C2 H2B 111.1 . . ?
N4 C2 C3 103.42(18) . . ?
H2A C2 H2B 109.0 . . ?
C3 C2 H2A 111.1 . . ?
C3 C2 H2B 111.1 . . ?
C5 C4 H4A 110.9 . . ?
C5 C4 H4B 110.9 . . ?
H4A C4 H4B 108.9 . . ?
C3 C4 C5 104.41(18) . . ?
C3 C4 H4A 110.9 . . ?
C3 C4 H4B 110.9 . . ?
C2 C3 C4 104.3(2) . . ?
C2 C3 H3A 110.9 . . ?
C2 C3 H3B 110.9 . . ?
C4 C3 H3A 110.9 . . ?
C4 C3 H3B 110.9 . . ?
H3A C3 H3B 108.9 . . ?

_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_5
_database_code_depnum_ccdc_archive 'CCDC 1530064'
_audit_update_record             
;
2017-01-29 deposited with the CCDC.
2017-07-10 downloaded from the CCDC.
;
_audit_creation_date             2017-01-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C8 H9 N4 Ni0.5 O)'
_chemical_formula_sum            'C16 H18 N8 Ni O2'
_chemical_formula_weight         413.09
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Ni C12 N5'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.5902(4)
_cell_length_b                   11.1021(7)
_cell_length_c                   12.3601(8)
_cell_angle_alpha                90.489(5)
_cell_angle_beta                 95.586(5)
_cell_angle_gamma                101.506(5)
_cell_volume                     881.59(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3337
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.5210
_cell_measurement_theta_min      4.0240
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.861
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0723
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6966
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.994
_diffrn_reflns_theta_min         3.595
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -32.00   33.00   1.0000    9.0600
omega____ theta____ kappa____ phi______ frames
    -      -40.1287   57.0000   60.0000 65

#__ type_ start__ end____ width___ exp.time_
  2 omega  -74.00   39.00   1.0000    9.0600
omega____ theta____ kappa____ phi______ frames
    -      -40.1287   77.0000  -90.0000 113

#__ type_ start__ end____ width___ exp.time_
  3 omega  -69.00   15.00   1.0000    9.0600
omega____ theta____ kappa____ phi______ frames
    -      -40.1287   57.0000 -180.0000 84

#__ type_ start__ end____ width___ exp.time_
  4 omega   11.00  118.00   1.0000    9.0600
omega____ theta____ kappa____ phi______ frames
    -       40.1287   77.0000    0.0000 107

#__ type_ start__ end____ width___ exp.time_
  5 omega   74.00   99.00   1.0000    9.0600
omega____ theta____ kappa____ phi______ frames
    -       40.1287  178.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega   40.00   75.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  150.0000 35

#__ type_ start__ end____ width___ exp.time_
  7 omega   50.00   95.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
  8 omega   30.00  172.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000  -60.0000 142

#__ type_ start__ end____ width___ exp.time_
  9 omega   85.00  153.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -30.0000 68

#__ type_ start__ end____ width___ exp.time_
 10 omega   83.00  115.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   60.0000 32

#__ type_ start__ end____ width___ exp.time_
 11 omega   64.00   91.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 12 omega   71.00  114.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  -30.0000 43

#__ type_ start__ end____ width___ exp.time_
 13 omega   39.00   96.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -150.0000 57

#__ type_ start__ end____ width___ exp.time_
 14 omega  101.00  162.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000 -150.0000 61

#__ type_ start__ end____ width___ exp.time_
 15 omega  117.00  145.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   60.0000 28

#__ type_ start__ end____ width___ exp.time_
 16 omega   43.00   86.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   30.0000 43

#__ type_ start__ end____ width___ exp.time_
 17 omega   90.00  115.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 18 omega   37.00   89.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   60.0000 52

#__ type_ start__ end____ width___ exp.time_
 19 omega   48.00   82.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -180.0000 34

#__ type_ start__ end____ width___ exp.time_
 20 omega   46.00   82.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -30.0000 36

#__ type_ start__ end____ width___ exp.time_
 21 omega   50.00  111.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -120.0000 61

#__ type_ start__ end____ width___ exp.time_
 22 omega   60.00  115.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  150.0000 55

#__ type_ start__ end____ width___ exp.time_
 23 omega   60.00   87.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
 24 omega  112.00  139.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 25 omega   71.00  115.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000    0.0000 44

#__ type_ start__ end____ width___ exp.time_
 26 omega   67.00  114.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  120.0000 47

#__ type_ start__ end____ width___ exp.time_
 27 omega  139.00  177.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -60.0000 38

#__ type_ start__ end____ width___ exp.time_
 28 omega   39.00   66.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 29 omega  131.00  177.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -180.0000 46

#__ type_ start__ end____ width___ exp.time_
 30 omega   67.00   94.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 31 omega   70.00  115.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -60.0000 45
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0457900000
_diffrn_orient_matrix_UB_12      -0.0209029000
_diffrn_orient_matrix_UB_13      -0.1240957000
_diffrn_orient_matrix_UB_21      -0.0287787000
_diffrn_orient_matrix_UB_22      -0.1398934000
_diffrn_orient_matrix_UB_23      0.0143604000
_diffrn_orient_matrix_UB_31      -0.2336091000
_diffrn_orient_matrix_UB_32      -0.0079363000
_diffrn_orient_matrix_UB_33      0.0095526000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2662
_reflns_number_total             3301
_reflns_odcompleteness_completeness 98.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     75.12
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         1.239
_refine_diff_density_min         -0.598
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0607
_refine_ls_restrained_S_all      1.092
_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)+(0.0881P)²+0.8375P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1503
_refine_ls_wR_factor_ref         0.1604
_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 C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2A(H2A), N2(H), C6(HA), C4(HB), C7(HC), C8(HD), C5(HH), C7A(H7A), C8A(H8A),
 C6A(H6A), C4A(H4A), C5A(H5A)
2.b Idealised Me refined as rotating group:
 C2(HE,HF,HG), C2A(H2AA,H2AB,H2AC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 1.0000 0.0000 1.0000 0.0175(2) Uani 1 2 d S T P . .
Ni1A Ni 0.5000 0.0000 1.0000 0.0181(2) Uani 1 2 d S T P . .
O1 O 0.8918(4) -0.16947(19) 0.82817(19) 0.0241(5) Uani 1 1 d . . . . .
O1A O 0.5207(4) 0.24363(19) 0.94864(19) 0.0248(5) Uani 1 1 d . . . . .
N2A N 0.4364(4) -0.0814(2) 0.8668(2) 0.0193(5) Uani 1 1 d . . . . .
H2A H 0.4284 -0.1611 0.8583 0.023 Uiso 1 1 calc R . . . .
N2 N 1.0033(4) 0.1483(2) 0.9335(2) 0.0204(6) Uani 1 1 d . . . . .
H H 1.0368 0.2195 0.9692 0.025 Uiso 1 1 calc R . . . .
N1A N 0.4839(4) 0.1360(2) 0.9127(2) 0.0194(5) Uani 1 1 d . . . . .
N1 N 0.9257(4) -0.0591(2) 0.8566(2) 0.0185(5) Uani 1 1 d . . . . .
N3 N 0.9071(4) 0.0201(2) 0.7790(2) 0.0193(5) Uani 1 1 d . . . . .
N3A N 0.4330(4) 0.1174(2) 0.8082(2) 0.0211(6) Uani 1 1 d . . . . .
N4 N 0.9370(4) 0.2321(2) 0.7625(2) 0.0225(6) Uani 1 1 d . . . . .
N4A N 0.3511(4) -0.0476(2) 0.6820(2) 0.0228(6) Uani 1 1 d . . . . .
C1A C 0.4040(5) -0.0093(3) 0.7854(3) 0.0192(6) Uani 1 1 d . . . . .
C1 C 0.9516(5) 0.1381(3) 0.8289(3) 0.0189(6) Uani 1 1 d . . . . .
C3 C 0.9923(5) 0.3568(3) 0.8053(3) 0.0217(7) Uani 1 1 d . . . . .
C6 C 1.0964(6) 0.5970(3) 0.8855(3) 0.0260(7) Uani 1 1 d . . . . .
HA H 1.1324 0.6795 0.9128 0.031 Uiso 1 1 calc R . . . .
C4 C 1.1966(5) 0.4061(3) 0.8435(3) 0.0230(7) Uani 1 1 d . . . . .
HB H 1.3008 0.3583 0.8415 0.028 Uiso 1 1 calc R . . . .
C7 C 0.8931(6) 0.5472(3) 0.8464(3) 0.0259(7) Uani 1 1 d . . . . .
HC H 0.7895 0.5957 0.8469 0.031 Uiso 1 1 calc R . . . .
C3A C 0.3358(6) -0.1749(3) 0.6518(2) 0.0239(7) Uani 1 1 d . . . . .
C8 C 0.8392(5) 0.4261(3) 0.8061(3) 0.0238(7) Uani 1 1 d . . . . .
HD H 0.6993 0.3916 0.7796 0.029 Uiso 1 1 calc R . . . .
C2 C 0.8590(7) 0.2139(3) 0.6479(3) 0.0324(8) Uani 1 1 d . . . . .
HE H 0.9722 0.2444 0.6031 0.049 Uiso 1 1 calc GR . . . .
HF H 0.7466 0.2590 0.6318 0.049 Uiso 1 1 calc GR . . . .
HG H 0.8059 0.1260 0.6318 0.049 Uiso 1 1 calc GR . . . .
C5 C 1.2477(5) 0.5267(3) 0.8850(3) 0.0250(7) Uani 1 1 d . . . . .
HH H 1.3870 0.5607 0.9130 0.030 Uiso 1 1 calc R . . . .
C2A C 0.2786(6) 0.0318(3) 0.5992(3) 0.0303(8) Uani 1 1 d . . . . .
H2AA H 0.1278 0.0056 0.5816 0.045 Uiso 1 1 calc GR . . . .
H2AB H 0.3486 0.0258 0.5335 0.045 Uiso 1 1 calc GR . . . .
H2AC H 0.3107 0.1171 0.6269 0.045 Uiso 1 1 calc GR . . . .
C7A C 0.1353(6) -0.3768(3) 0.6065(3) 0.0314(8) Uani 1 1 d . . . . .
H7A H 0.0042 -0.4315 0.5941 0.038 Uiso 1 1 calc R . . . .
C8A C 0.1445(6) -0.2545(3) 0.6358(3) 0.0278(7) Uani 1 1 d . . . . .
H8A H 0.0205 -0.2258 0.6449 0.033 Uiso 1 1 calc R . . . .
C6A C 0.3153(6) -0.4192(3) 0.5951(3) 0.0327(8) Uani 1 1 d . . . . .
H6A H 0.3080 -0.5030 0.5756 0.039 Uiso 1 1 calc R . . . .
C4A C 0.5182(6) -0.2167(3) 0.6401(3) 0.0286(7) Uani 1 1 d . . . . .
H4A H 0.6493 -0.1616 0.6510 0.034 Uiso 1 1 calc R . . . .
C5A C 0.5072(6) -0.3392(3) 0.6123(3) 0.0353(8) Uani 1 1 d . . . . .
H5A H 0.6312 -0.3685 0.6050 0.042 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ni1 0.0254(4) 0.0080(3) 0.0186(4) 0.0009(2) 0.0013(3) 0.0026(3)
Ni1A 0.0247(4) 0.0106(4) 0.0182(4) -0.0001(3) 0.0000(3) 0.0029(3)
O1 0.0333(13) 0.0103(10) 0.0287(12) -0.0010(8) 0.0012(10) 0.0052(8)
O1A 0.0315(13) 0.0115(10) 0.0300(12) -0.0010(8) -0.0001(10) 0.0026(8)
N2A 0.0233(14) 0.0127(11) 0.0214(12) -0.0007(9) -0.0011(10) 0.0037(9)
N2 0.0298(15) 0.0075(11) 0.0232(13) 0.0004(9) 0.0019(11) 0.0024(9)
N1A 0.0215(14) 0.0130(11) 0.0237(13) 0.0019(9) 0.0020(10) 0.0040(9)
N1 0.0193(14) 0.0113(11) 0.0243(13) 0.0009(9) 0.0019(10) 0.0020(9)
N3 0.0237(14) 0.0130(12) 0.0204(12) 0.0006(9) 0.0005(10) 0.0026(9)
N3A 0.0249(15) 0.0148(12) 0.0228(13) 0.0018(10) 0.0005(11) 0.0030(10)
N4 0.0318(15) 0.0114(12) 0.0233(14) 0.0012(10) -0.0001(11) 0.0037(10)
N4A 0.0285(15) 0.0167(12) 0.0233(13) 0.0010(10) -0.0014(11) 0.0070(10)
C1A 0.0196(16) 0.0148(14) 0.0227(15) -0.0015(11) 0.0015(12) 0.0028(11)
C1 0.0206(16) 0.0099(13) 0.0260(15) 0.0022(11) 0.0026(12) 0.0027(10)
C3 0.0315(18) 0.0107(13) 0.0222(15) 0.0032(11) 0.0030(13) 0.0019(12)
C6 0.039(2) 0.0124(14) 0.0265(16) 0.0031(11) 0.0061(14) 0.0041(13)
C4 0.0291(18) 0.0152(14) 0.0256(16) 0.0044(11) 0.0040(13) 0.0061(12)
C7 0.0339(19) 0.0150(14) 0.0309(17) 0.0027(12) 0.0076(15) 0.0075(13)
C3A 0.0354(19) 0.0188(15) 0.0169(14) -0.0013(11) -0.0008(13) 0.0054(13)
C8 0.0264(18) 0.0149(14) 0.0294(16) 0.0060(12) 0.0019(13) 0.0027(12)
C2 0.054(2) 0.0192(15) 0.0231(17) 0.0004(12) -0.0040(15) 0.0083(15)
C5 0.0288(18) 0.0176(15) 0.0268(16) 0.0033(12) 0.0004(13) 0.0012(12)
C2A 0.042(2) 0.0247(16) 0.0248(17) 0.0024(13) -0.0024(15) 0.0112(14)
C7A 0.040(2) 0.0235(16) 0.0271(17) -0.0017(13) 0.0048(15) -0.0023(14)
C8A 0.033(2) 0.0251(16) 0.0250(16) -0.0013(12) 0.0050(14) 0.0035(14)
C6A 0.051(2) 0.0226(16) 0.0247(17) -0.0027(13) -0.0009(16) 0.0098(15)
C4A 0.0280(19) 0.0275(17) 0.0297(17) -0.0045(13) -0.0043(14) 0.0076(13)
C5A 0.038(2) 0.0319(19) 0.037(2) -0.0075(15) -0.0054(16) 0.0155(16)

_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 N2 1.844(2) . ?
Ni1 N2 1.844(2) 2_757 ?
Ni1 N1 1.869(3) . ?
Ni1 N1 1.869(3) 2_757 ?
Ni1A N2A 1.842(3) . ?
Ni1A N2A 1.842(3) 2_657 ?
Ni1A N1A 1.878(3) . ?
Ni1A N1A 1.878(3) 2_657 ?
O1 N1 1.242(3) . ?
O1A N1A 1.240(3) . ?
N2A H2A 0.8800 . ?
N2A C1A 1.319(4) . ?
N2 H 0.8800 . ?
N2 C1 1.303(4) . ?
N1A N3A 1.307(4) . ?
N1 N3 1.320(4) . ?
N3 C1 1.407(4) . ?
N3A C1A 1.404(4) . ?
N4 C1 1.346(4) . ?
N4 C3 1.442(4) . ?
N4 C2 1.457(4) . ?
N4A C1A 1.334(4) . ?
N4A C3A 1.440(4) . ?
N4A C2A 1.463(4) . ?
C3 C4 1.383(5) . ?
C3 C8 1.386(5) . ?
C6 HA 0.9500 . ?
C6 C7 1.382(5) . ?
C6 C5 1.384(5) . ?
C4 HB 0.9500 . ?
C4 C5 1.394(4) . ?
C7 HC 0.9500 . ?
C7 C8 1.394(4) . ?
C3A C8A 1.383(5) . ?
C3A C4A 1.391(5) . ?
C8 HD 0.9500 . ?
C2 HE 0.9800 . ?
C2 HF 0.9800 . ?
C2 HG 0.9800 . ?
C5 HH 0.9500 . ?
C2A H2AA 0.9800 . ?
C2A H2AB 0.9800 . ?
C2A H2AC 0.9800 . ?
C7A H7A 0.9500 . ?
C7A C8A 1.391(5) . ?
C7A C6A 1.379(6) . ?
C8A H8A 0.9500 . ?
C6A H6A 0.9500 . ?
C6A C5A 1.390(6) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.386(5) . ?
C5A H5A 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
N2 Ni1 N2 180.0 . 2_757 ?
N2 Ni1 N1 81.43(11) . . ?
N2 Ni1 N1 98.57(11) . 2_757 ?
N2 Ni1 N1 81.43(11) 2_757 2_757 ?
N2 Ni1 N1 98.57(11) 2_757 . ?
N1 Ni1 N1 180.0 2_757 . ?
N2A Ni1A N2A 180.0 . 2_657 ?
N2A Ni1A N1A 81.46(11) . . ?
N2A Ni1A N1A 81.46(11) 2_657 2_657 ?
N2A Ni1A N1A 98.54(11) 2_657 . ?
N2A Ni1A N1A 98.54(11) . 2_657 ?
N1A Ni1A N1A 180.0 2_657 . ?
Ni1A N2A H2A 123.1 . . ?
C1A N2A Ni1A 113.8(2) . . ?
C1A N2A H2A 123.1 . . ?
Ni1 N2 H 123.0 . . ?
C1 N2 Ni1 113.9(2) . . ?
C1 N2 H 123.0 . . ?
O1A N1A Ni1A 123.6(2) . . ?
O1A N1A N3A 117.7(2) . . ?
N3A N1A Ni1A 118.74(19) . . ?
O1 N1 Ni1 124.4(2) . . ?
O1 N1 N3 116.6(3) . . ?
N3 N1 Ni1 118.91(19) . . ?
N1 N3 C1 107.1(2) . . ?
N1A N3A C1A 108.0(2) . . ?
C1 N4 C3 119.9(3) . . ?
C1 N4 C2 122.7(3) . . ?
C3 N4 C2 117.4(3) . . ?
C1A N4A C3A 120.1(3) . . ?
C1A N4A C2A 122.0(3) . . ?
C3A N4A C2A 117.4(3) . . ?
N2A C1A N3A 117.9(3) . . ?
N2A C1A N4A 124.8(3) . . ?
N4A C1A N3A 117.3(3) . . ?
N2 C1 N3 118.6(3) . . ?
N2 C1 N4 125.4(3) . . ?
N4 C1 N3 116.0(3) . . ?
C4 C3 N4 119.8(3) . . ?
C4 C3 C8 121.0(3) . . ?
C8 C3 N4 119.2(3) . . ?
C7 C6 HA 120.0 . . ?
C7 C6 C5 120.1(3) . . ?
C5 C6 HA 120.0 . . ?
C3 C4 HB 120.4 . . ?
C3 C4 C5 119.2(3) . . ?
C5 C4 HB 120.4 . . ?
C6 C7 HC 119.9 . . ?
C6 C7 C8 120.2(3) . . ?
C8 C7 HC 119.9 . . ?
C8A C3A N4A 120.9(3) . . ?
C8A C3A C4A 120.6(3) . . ?
C4A C3A N4A 118.6(3) . . ?
C3 C8 C7 119.2(3) . . ?
C3 C8 HD 120.4 . . ?
C7 C8 HD 120.4 . . ?
N4 C2 HE 109.5 . . ?
N4 C2 HF 109.5 . . ?
N4 C2 HG 109.5 . . ?
HE C2 HF 109.5 . . ?
HE C2 HG 109.5 . . ?
HF C2 HG 109.5 . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 HH 119.9 . . ?
C4 C5 HH 119.9 . . ?
N4A C2A H2AA 109.5 . . ?
N4A C2A H2AB 109.5 . . ?
N4A C2A H2AC 109.5 . . ?
H2AA C2A H2AB 109.5 . . ?
H2AA C2A H2AC 109.5 . . ?
H2AB C2A H2AC 109.5 . . ?
C8A C7A H7A 119.8 . . ?
C6A C7A H7A 119.8 . . ?
C6A C7A C8A 120.5(3) . . ?
C3A C8A C7A 119.4(3) . . ?
C3A C8A H8A 120.3 . . ?
C7A C8A H8A 120.3 . . ?
C7A C6A H6A 120.1 . . ?
C7A C6A C5A 119.9(3) . . ?
C5A C6A H6A 120.1 . . ?
C3A C4A H4A 120.3 . . ?
C5A C4A C3A 119.5(3) . . ?
C5A C4A H4A 120.3 . . ?
C6A C5A H5A 119.9 . . ?
C4A C5A C6A 120.2(4) . . ?
C4A C5A H5A 119.9 . . ?

_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_1
_database_code_depnum_ccdc_archive 'CCDC 1530063'
_audit_update_record             
;
2017-01-29 deposited with the CCDC.
2017-07-10 downloaded from the CCDC.
;
_audit_creation_date             2017-01-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H14 N8 Ni O2'
_chemical_formula_sum            'C6 H14 N8 Ni O2'
_chemical_formula_weight         288.96
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C6 H12 N6 O4 cl2 ni1'
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 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                   5.4378(10)
_cell_length_b                   6.6766(12)
_cell_length_c                   15.437(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.885(16)
_cell_angle_gamma                90
_cell_volume                     556.40(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    768
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.0010
_cell_measurement_theta_min      5.7370
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.624
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74293
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            2788
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.492
_diffrn_reflns_theta_min         5.774
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -45.00   32.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  120.0000 77

#__ type_ start__ end____ width___ exp.time_
  2 omega -129.00  -36.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  178.0000 -150.0000 93

#__ type_ start__ end____ width___ exp.time_
  3 omega  -58.00  -14.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -38.0000  150.0000 44

#__ type_ start__ end____ width___ exp.time_
  4 omega   25.00   55.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  -99.0000 -180.0000 30

#__ type_ start__ end____ width___ exp.time_
  5 omega   54.00   87.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   60.0000 33

#__ type_ start__ end____ width___ exp.time_
  6 omega  117.00  142.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
  7 omega   39.00   96.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  -60.0000 57

#__ type_ start__ end____ width___ exp.time_
  8 omega   85.00  170.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -90.0000 85

#__ type_ start__ end____ width___ exp.time_
  9 omega   82.00  141.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000   90.0000 59

#__ type_ start__ end____ width___ exp.time_
 10 omega   45.00   72.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 11 omega   52.00   79.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
 12 omega   42.00   68.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   74.00  115.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -120.0000 41

#__ type_ start__ end____ width___ exp.time_
 14 omega  117.00  163.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000    0.0000 46

#__ type_ start__ end____ width___ exp.time_
 15 omega   85.00  125.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -180.0000 40

#__ type_ start__ end____ width___ exp.time_
 16 omega   41.00   71.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000    0.0000 30

#__ type_ start__ end____ width___ exp.time_
 17 omega  132.00  169.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000   30.0000 37

#__ type_ start__ end____ width___ exp.time_
 18 omega   81.00  108.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
 19 omega   76.00  141.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000 -120.0000 65

#__ type_ start__ end____ width___ exp.time_
 20 omega  -48.00   14.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000 -150.0000 62

#__ type_ start__ end____ width___ exp.time_
 21 omega  -49.00  -20.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  -60.0000 29

#__ type_ start__ end____ width___ exp.time_
 22 omega  -12.00   15.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  -60.0000 27
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1568927000
_diffrn_orient_matrix_UB_12      0.1721068000
_diffrn_orient_matrix_UB_13      0.0443337000
_diffrn_orient_matrix_UB_21      0.2371362000
_diffrn_orient_matrix_UB_22      -0.1033853000
_diffrn_orient_matrix_UB_23      -0.0228275000
_diffrn_orient_matrix_UB_31      -0.0218647000
_diffrn_orient_matrix_UB_32      0.1144791000
_diffrn_orient_matrix_UB_33      -0.0871860000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                878
_reflns_number_total             1105
_reflns_odcompleteness_completeness 94.37
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     81
_refine_ls_number_reflns         1105
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0497
_refine_ls_restrained_S_all      1.073
_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)+(0.0626P)²+0.3647P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1380
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2)
2.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.0000 0.5000 0.0000 0.0214(3) Uani 1 2 d S T P . .
O1 O 0.1369(5) 0.8707(4) 0.07033(16) 0.0293(6) Uani 1 1 d . . . . .
N1 N 0.1920(5) 0.6886(4) 0.06787(18) 0.0227(6) Uani 1 1 d . . . . .
N3 N 0.3940(5) 0.6285(5) 0.11590(17) 0.0229(6) Uani 1 1 d . . . . .
N2 N 0.2404(5) 0.3299(4) 0.05204(18) 0.0241(6) Uani 1 1 d . . . . .
H2 H 0.2380 0.1997 0.0431 0.029 Uiso 1 1 calc R . . . .
N4 N 0.6183(6) 0.3372(5) 0.14621(19) 0.0273(7) Uani 1 1 d . . . . .
C1 C 0.4161(6) 0.4204(6) 0.1039(2) 0.0243(7) Uani 1 1 d . . . . .
C3 C 0.7974(7) 0.4499(6) 0.2065(2) 0.0289(8) Uani 1 1 d . . . . .
H3A H 0.7615 0.5934 0.2008 0.043 Uiso 1 1 calc GR . . . .
H3B H 0.9655 0.4240 0.1924 0.043 Uiso 1 1 calc GR . . . .
H3C H 0.7845 0.4073 0.2666 0.043 Uiso 1 1 calc GR . . . .
C2 C 0.6637(7) 0.1224(6) 0.1405(3) 0.0329(8) Uani 1 1 d . . . . .
H2A H 0.6045 0.0545 0.1903 0.049 Uiso 1 1 calc GR . . . .
H2B H 0.8417 0.0985 0.1411 0.049 Uiso 1 1 calc GR . . . .
H2C H 0.5753 0.0700 0.0862 0.049 Uiso 1 1 calc GR . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ni1 0.0234(5) 0.0190(5) 0.0196(4) 0.0000(3) -0.0059(3) 0.0018(3)
O1 0.0343(13) 0.0186(12) 0.0324(12) -0.0027(10) -0.0061(10) 0.0032(11)
N1 0.0273(14) 0.0176(14) 0.0216(12) 0.0019(10) -0.0036(11) 0.0005(11)
N3 0.0231(14) 0.0233(15) 0.0203(12) 0.0002(11) -0.0053(11) 0.0003(12)
N2 0.0262(14) 0.0196(15) 0.0241(13) -0.0035(11) -0.0074(11) 0.0045(12)
N4 0.0256(15) 0.0263(16) 0.0280(14) 0.0017(12) -0.0046(12) -0.0009(13)
C1 0.0255(16) 0.0276(18) 0.0188(14) 0.0010(12) -0.0012(12) 0.0032(14)
C3 0.0258(16) 0.034(2) 0.0248(16) 0.0001(14) -0.0064(13) 0.0008(15)
C2 0.0301(18) 0.0280(19) 0.0378(19) 0.0032(16) -0.0075(15) 0.0089(16)

_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 1.874(3) . ?
Ni1 N1 1.874(3) 3_565 ?
Ni1 N2 1.842(3) . ?
Ni1 N2 1.842(3) 3_565 ?
O1 N1 1.254(4) . ?
N1 N3 1.312(4) . ?
N3 C1 1.409(5) . ?
N2 H2 0.8800 . ?
N2 C1 1.318(4) . ?
N4 C1 1.331(4) . ?
N4 C3 1.471(4) . ?
N4 C2 1.460(5) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 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 180.00(15) . 3_565 ?
N2 Ni1 N1 81.47(13) 3_565 3_565 ?
N2 Ni1 N1 81.47(13) . . ?
N2 Ni1 N1 98.53(13) . 3_565 ?
N2 Ni1 N1 98.53(13) 3_565 . ?
N2 Ni1 N2 180.0 . 3_565 ?
O1 N1 Ni1 123.3(2) . . ?
O1 N1 N3 117.8(3) . . ?
N3 N1 Ni1 118.9(2) . . ?
N1 N3 C1 107.8(3) . . ?
Ni1 N2 H2 123.0 . . ?
C1 N2 Ni1 114.1(2) . . ?
C1 N2 H2 123.0 . . ?
C1 N4 C3 122.9(3) . . ?
C1 N4 C2 121.0(3) . . ?
C2 N4 C3 115.9(3) . . ?
N2 C1 N3 117.7(3) . . ?
N2 C1 N4 127.1(3) . . ?
N4 C1 N3 115.2(3) . . ?
N4 C3 H3A 109.5 . . ?
N4 C3 H3B 109.5 . . ?
N4 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N4 C2 H2A 109.5 . . ?
N4 C2 H2B 109.5 . . ?
N4 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ni1 N1 N3 C1 -0.5(3) . . . . ?
Ni1 N2 C1 N3 2.6(4) . . . . ?
Ni1 N2 C1 N4 -176.3(3) . . . . ?
O1 N1 N3 C1 179.1(3) . . . . ?
N1 Ni1 N2 C1 -2.2(2) . . . . ?
N1 Ni1 N2 C1 177.8(2) 3_565 . . . ?
N1 N3 C1 N2 -1.4(4) . . . . ?
N1 N3 C1 N4 177.7(3) . . . . ?
N2 Ni1 N1 O1 2.0(3) 3_565 . . . ?
N2 Ni1 N1 O1 -178.0(3) . . . . ?
N2 Ni1 N1 N3 1.5(2) . . . . ?
N2 Ni1 N1 N3 -178.5(2) 3_565 . . . ?
C3 N4 C1 N3 4.5(5) . . . . ?
C3 N4 C1 N2 -176.6(3) . . . . ?
C2 N4 C1 N3 179.3(3) . . . . ?
C2 N4 C1 N2 -1.8(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
