# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1855263'
_audit_update_record             
;
2018-07-11 deposited with the CCDC.
2018-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL
_chemical_name_systematic        
'N-(2-((2-mercaptoethyl)amino)ethyl)-1-methyl-1H-imidazole -2-carboxamido nickel(II)'
_chemical_name_common            
'N-(2-((2-mercaptoethyl)amino)ethyl)-1-methyl-1H-imidazole -2-carboxamido nickel(II)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H14 N4 Ni O S, H2 O'
_chemical_formula_sum            'C9 H16 N4 Ni O2 S'
_chemical_formula_weight         303.03

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc '

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

_cell_length_a                   11.9515(15)
_cell_length_b                   4.8375(6)
_cell_length_c                   22.198(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.424(2)
_cell_angle_gamma                90.00
_cell_volume                     1248.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6229
_cell_measurement_theta_min      3.51
_cell_measurement_theta_max      25.14

_exptl_crystal_description       cube
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    1.717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.636
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
SADABS; Sheldrick, (1996).
;

_exptl_special_details           
; 
Data were collected with a Bruker SMART APEX CCD-based diffractometer
using /w-scans of width 0.3 deg. and 30s duration at a
crystal-to-detector distance of 4.908 cm. Intensity decay over
the course of the data collection was evaluated by recollecting
the first 50 frames of data at the end of the experiment. No
significant decay was noted.  
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SMART APEX CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        <0.1
_diffrn_reflns_number            8216
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         25.12
_reflns_number_total             2227
_reflns_number_gt                2107
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART 5.628 (Bruker, 2002)'
_computing_cell_refinement       'SAINT 6.36 (Bruker, 2002)'
_computing_data_reduction        'SAINT 6.36 (Bruker, 2002)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997) and Mercury (Macraeet al., 2006)'
_computing_publication_material  'PLATON (Spek, 2009)'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0563P)²+3.8734P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2227
_refine_ls_number_parameters     210
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1164
_refine_ls_wR_factor_gt          0.1148
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.28185(4) 0.44266(11) 0.32174(2) 0.02292(19) Uani 1 1 d . . .
S1 S 0.39559(8) 0.6449(2) 0.39950(5) 0.0326(3) Uani 1 1 d . . .
O1 O 0.1243(2) 0.1837(7) 0.15311(13) 0.0355(7) Uani 1 1 d . . .
N1 N 0.3250(3) 0.6211(7) 0.25511(14) 0.0236(7) Uani 1 1 d . . .
N2 N 0.3076(3) 0.6380(8) 0.15493(15) 0.0308(8) Uani 1 1 d . . .
N3 N 0.1770(2) 0.2614(7) 0.25897(14) 0.0232(7) Uani 1 1 d . . .
N4 N 0.2224(3) 0.2155(8) 0.37631(15) 0.0303(8) Uani 1 1 d . . .
H4 H 0.267(5) 0.059(12) 0.379(2) 0.046(14) Uiso 1 1 d . . .
C1 C 0.2703(3) 0.5159(8) 0.20088(17) 0.0257(8) Uani 1 1 d . . .
C2 C 0.3986(3) 0.8194(9) 0.2430(2) 0.0285(9) Uani 1 1 d . . .
H2 H 0.443(4) 0.932(11) 0.272(2) 0.043(14) Uiso 1 1 d . . .
C3 C 0.3885(3) 0.8314(10) 0.1813(2) 0.0334(9) Uani 1 1 d . . .
H3 H 0.424(4) 0.943(11) 0.158(2) 0.043(14) Uiso 1 1 d . . .
C4 C 0.2699(5) 0.5830(14) 0.0885(2) 0.0564(15) Uani 1 1 d . . .
H4A H 0.2362 0.3975 0.0821 0.085 Uiso 1 1 calc R . .
H4B H 0.3360 0.5944 0.0695 0.085 Uiso 1 1 calc R . .
H4C H 0.2121 0.7201 0.0694 0.085 Uiso 1 1 calc R . .
C5 C 0.1812(3) 0.2981(8) 0.20083(17) 0.0244(8) Uani 1 1 d . . .
C6 C 0.1039(3) 0.0542(9) 0.2788(2) 0.0288(9) Uani 1 1 d . . .
H6A H 0.132(4) -0.142(12) 0.277(2) 0.041(13) Uiso 1 1 d . . .
H6B H 0.033(4) 0.056(10) 0.254(2) 0.036(13) Uiso 1 1 d . . .
C7 C 0.1032(3) 0.1320(10) 0.3450(2) 0.0334(10) Uani 1 1 d . . .
H7A H 0.056(4) 0.294(11) 0.348(2) 0.037(12) Uiso 1 1 d . . .
H7B H 0.076(4) -0.018(10) 0.368(2) 0.034(12) Uiso 1 1 d . . .
C8 C 0.2355(4) 0.3371(12) 0.4385(2) 0.0394(11) Uani 1 1 d . . .
H8A H 0.188(4) 0.505(11) 0.437(2) 0.036(13) Uiso 1 1 d . . .
H8B H 0.222(4) 0.205(12) 0.466(2) 0.045(14) Uiso 1 1 d . . .
C9 C 0.3586(4) 0.4289(13) 0.4602(2) 0.0431(11) Uani 1 1 d . . .
H9A H 0.372(5) 0.532(12) 0.498(3) 0.053(16) Uiso 1 1 d . . .
H9B H 0.410(5) 0.259(13) 0.469(2) 0.052(15) Uiso 1 1 d . . .
O2 O -0.0053(3) 0.2496(8) 0.03058(15) 0.0465(8) Uani 1 1 d D . .
H2OA H 0.039(4) 0.233(13) 0.0686(12) 0.058(16) Uiso 1 1 d D . .
H2OB H 0.008(13) 0.090(16) 0.014(6) 0.07(3) Uiso 0.50 1 d PD . .
H2OC H 0.005(12) 0.425(9) 0.022(6) 0.07(3) Uiso 0.50 1 d PD . .


_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 N3 1.863(3) . yes
Ni1 N1 1.885(3) . yes
Ni1 N4 1.892(3) . yes
Ni1 S1 2.1668(11) . yes
S1 C9 1.839(5) . no
O1 C5 1.248(5) . no
N1 C1 1.330(5) . no
N1 C2 1.370(5) . no
N2 C1 1.341(5) . no
N2 C3 1.375(6) . no
N2 C4 1.463(6) . no
N3 C5 1.315(5) . no
N3 C6 1.463(5) . no
N4 C8 1.476(6) . no
N4 C7 1.489(5) . no
N4 H4 0.92(6) . no
C1 C5 1.498(5) . no
C2 C3 1.350(6) . no
C2 H2 0.91(5) . no
C3 H3 0.92(5) . no
C4 H4A 0.9800 . no
C4 H4B 0.9800 . no
C4 H4C 0.9800 . no
C6 C7 1.520(6) . no
C6 H6A 1.01(6) . no
C6 H6B 0.89(5) . no
C7 H7A 0.98(5) . no
C7 H7B 0.98(5) . no
C8 C9 1.505(7) . no
C8 H8A 0.99(5) . no
C8 H8B 0.93(6) . no
C9 H9A 0.95(6) . no
C9 H9B 1.01(6) . no
O2 H2OA 0.888(14) . no
O2 H2OB 0.884(14) . no
O2 H2OC 0.886(15) . no

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
N3 Ni1 N1 83.55(13) . . no
N3 Ni1 N4 85.30(14) . . no
N1 Ni1 N4 168.59(15) . . no
N3 Ni1 S1 175.63(10) . . no
N1 Ni1 S1 100.55(10) . . no
N4 Ni1 S1 90.66(11) . . no
C9 S1 Ni1 96.56(17) . . no
C1 N1 C2 107.1(3) . . no
C1 N1 Ni1 111.6(3) . . no
C2 N1 Ni1 141.2(3) . . no
C1 N2 C3 107.6(3) . . no
C1 N2 C4 127.4(4) . . no
C3 N2 C4 125.0(4) . . no
C5 N3 C6 123.3(3) . . no
C5 N3 Ni1 119.9(3) . . no
C6 N3 Ni1 116.3(2) . . no
C8 N4 C7 115.2(3) . . no
C8 N4 Ni1 113.2(3) . . no
C7 N4 Ni1 108.7(3) . . no
C8 N4 H4 109(3) . . no
C7 N4 H4 107(3) . . no
Ni1 N4 H4 103(3) . . no
N1 C1 N2 109.9(4) . . no
N1 C1 C5 118.0(3) . . no
N2 C1 C5 132.1(4) . . no
C3 C2 N1 108.6(4) . . no
C3 C2 H2 126(3) . . no
N1 C2 H2 125(3) . . no
C2 C3 N2 106.9(4) . . no
C2 C3 H3 131(3) . . no
N2 C3 H3 122(3) . . no
N2 C4 H4A 109.5 . . no
N2 C4 H4B 109.5 . . no
H4A C4 H4B 109.5 . . no
N2 C4 H4C 109.5 . . no
H4A C4 H4C 109.5 . . no
H4B C4 H4C 109.5 . . no
O1 C5 N3 129.5(4) . . no
O1 C5 C1 124.1(3) . . no
N3 C5 C1 106.5(3) . . no
N3 C6 C7 105.0(3) . . no
N3 C6 H6A 114(3) . . no
C7 C6 H6A 110(3) . . no
N3 C6 H6B 111(3) . . no
C7 C6 H6B 112(3) . . no
H6A C6 H6B 105(4) . . no
N4 C7 C6 107.4(3) . . no
N4 C7 H7A 105(3) . . no
C6 C7 H7A 113(3) . . no
N4 C7 H7B 111(3) . . no
C6 C7 H7B 113(3) . . no
H7A C7 H7B 107(4) . . no
N4 C8 C9 107.5(3) . . no
N4 C8 H8A 112(3) . . no
C9 C8 H8A 106(3) . . no
N4 C8 H8B 110(3) . . no
C9 C8 H8B 107(3) . . no
H8A C8 H8B 113(4) . . no
C8 C9 S1 108.4(3) . . no
C8 C9 H9A 113(3) . . no
S1 C9 H9A 109(4) . . no
C8 C9 H9B 109(3) . . no
S1 C9 H9B 111(3) . . no
H9A C9 H9B 107(4) . . no
H2OA O2 H2OB 102(10) . . no
H2OA O2 H2OC 102(9) . . no
H2OB O2 H2OC 134(10) . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Ni1 S1 C9 -173.69(19) . . . . no
N4 Ni1 S1 C9 4.2(2) . . . . no
N3 Ni1 N1 C1 -5.6(3) . . . . no
N4 Ni1 N1 C1 6.9(9) . . . . no
S1 Ni1 N1 C1 175.9(2) . . . . no
N3 Ni1 N1 C2 178.1(4) . . . . no
N4 Ni1 N1 C2 -169.4(6) . . . . no
S1 Ni1 N1 C2 -0.3(4) . . . . no
N1 Ni1 N3 C5 6.7(3) . . . . no
N4 Ni1 N3 C5 -170.8(3) . . . . no
N1 Ni1 N3 C6 178.6(3) . . . . no
N4 Ni1 N3 C6 1.0(3) . . . . no
N3 Ni1 N4 C8 -154.4(3) . . . . no
N1 Ni1 N4 C8 -166.9(6) . . . . no
S1 Ni1 N4 C8 23.9(3) . . . . no
N3 Ni1 N4 C7 -25.1(3) . . . . no
N1 Ni1 N4 C7 -37.5(9) . . . . no
S1 Ni1 N4 C7 153.2(3) . . . . no
C2 N1 C1 N2 0.8(4) . . . . no
Ni1 N1 C1 N2 -176.8(2) . . . . no
C2 N1 C1 C5 -178.2(3) . . . . no
Ni1 N1 C1 C5 4.3(4) . . . . no
C3 N2 C1 N1 -0.7(4) . . . . no
C4 N2 C1 N1 180.0(4) . . . . no
C3 N2 C1 C5 178.0(4) . . . . no
C4 N2 C1 C5 -1.3(7) . . . . no
C1 N1 C2 C3 -0.5(4) . . . . no
Ni1 N1 C2 C3 175.9(3) . . . . no
N1 C2 C3 N2 0.0(5) . . . . no
C1 N2 C3 C2 0.4(5) . . . . no
C4 N2 C3 C2 179.7(4) . . . . no
C6 N3 C5 O1 3.7(6) . . . . no
Ni1 N3 C5 O1 175.0(3) . . . . no
C6 N3 C5 C1 -176.9(3) . . . . no
Ni1 N3 C5 C1 -5.6(4) . . . . no
N1 C1 C5 O1 -179.9(4) . . . . no
N2 C1 C5 O1 1.4(7) . . . . no
N1 C1 C5 N3 0.6(5) . . . . no
N2 C1 C5 N3 -178.0(4) . . . . no
C5 N3 C6 C7 -166.2(3) . . . . no
Ni1 N3 C6 C7 22.3(4) . . . . no
C8 N4 C7 C6 171.5(4) . . . . no
Ni1 N4 C7 C6 43.3(4) . . . . no
N3 C6 C7 N4 -40.9(4) . . . . no
C7 N4 C8 C9 -175.5(4) . . . . no
Ni1 N4 C8 C9 -49.6(5) . . . . no
N4 C8 C9 S1 51.5(5) . . . . no
Ni1 S1 C9 C8 -30.7(4) . . . . no

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.12
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.900
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.088

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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 1855265'
_audit_update_record             
;
2018-07-11 deposited with the CCDC.
2018-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL
_chemical_name_systematic        
'Bis-(N-(2-aminoethyl)-1-methyl-1H-imidazole-2-carboxamido) nickel(II)'
_chemical_name_common            
'Bis-(N-(2-aminoethyl)-1-methyl-1H-imidazole-2-carboxamido) nickel(II)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H22 N8 Ni O2, H2 O'
_chemical_formula_sum            'C14 H24 N8 Ni O3'
_chemical_formula_weight         411.12

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2/n
_symmetry_space_group_name_Hall  '-P 2yac '

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

_cell_length_a                   9.1756(19)
_cell_length_b                   10.590(2)
_cell_length_c                   9.4434(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.876(3)
_cell_angle_gamma                90.00
_cell_volume                     906.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4744
_cell_measurement_theta_min      2.895
_cell_measurement_theta_max      25.125

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
_exptl_absorpt_coefficient_mu    1.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.571
_exptl_absorpt_correction_T_max  0.710
_exptl_absorpt_process_details   
;
SADABS; Sheldrick, (1996).
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SMART APEX CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6422
_diffrn_reflns_av_R_equivalents  0.0141
_diffrn_reflns_av_sigmaI/netI    0.0124
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.91
_diffrn_reflns_theta_max         25.08
_reflns_number_total             1621
_reflns_number_gt                1591
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART 5.628 (Bruker, 2002)'
_computing_cell_refinement       'SAINT 6.36 (Bruker, 2002)'
_computing_data_reduction        'SAINT 6.36 (Bruker, 2002)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997) and Mercury (Macraeet al., 2006)'
_computing_publication_material  'PLATON (Spek, 2009)'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0316P)²+0.6271P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1621
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0222
_refine_ls_R_factor_gt           0.0219
_refine_ls_wR_factor_ref         0.0569
_refine_ls_wR_factor_gt          0.0567
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.7500 0.60097(2) 0.7500 0.01456(10) Uani 1 2 d S . .
O1 O 0.35973(11) 0.72937(10) 0.51929(11) 0.0184(2) Uani 1 1 d . . .
N1 N 0.75632(13) 0.74473(11) 0.59259(13) 0.0172(3) Uani 1 1 d . . .
N2 N 0.61939(14) 0.86660(12) 0.43450(13) 0.0189(3) Uani 1 1 d . . .
N3 N 0.53823(14) 0.60482(11) 0.65419(13) 0.0166(3) Uani 1 1 d . . .
N4 N 0.65744(14) 0.46504(13) 0.87990(13) 0.0172(3) Uani 1 1 d . . .
H4NA H 0.713(2) 0.4028(18) 0.917(2) 0.025(5) Uiso 1 1 d . . .
H4NB H 0.6354(19) 0.5112(17) 0.949(2) 0.018(4) Uiso 1 1 d . . .
C2 C 0.84592(17) 0.83119(15) 0.54008(17) 0.0206(3) Uani 1 1 d . . .
H2 H 0.946(2) 0.8345(17) 0.5722(19) 0.025 Uiso 1 1 d . . .
C3 C 0.76330(18) 0.90676(14) 0.44243(17) 0.0219(3) Uani 1 1 d . . .
H3 H 0.7866(19) 0.9734(17) 0.3889(18) 0.020(4) Uiso 1 1 d . . .
C1 C 0.62012(16) 0.76841(14) 0.52704(15) 0.0166(3) Uani 1 1 d . . .
C5 C 0.49139(16) 0.69635(13) 0.56671(15) 0.0157(3) Uani 1 1 d . . .
C6 C 0.43504(16) 0.52600(14) 0.71601(16) 0.0181(3) Uani 1 1 d . . .
H6A H 0.3572(19) 0.4929(16) 0.6428(18) 0.020(4) Uiso 1 1 d . . .
H6B H 0.3894(19) 0.5748(16) 0.7856(18) 0.016(4) Uiso 1 1 d . . .
C7 C 0.52225(16) 0.41579(14) 0.79114(16) 0.0179(3) Uani 1 1 d . . .
H7A H 0.4619(19) 0.3656(16) 0.8469(17) 0.014(4) Uiso 1 1 d . . .
H7B H 0.5547(19) 0.3588(16) 0.7186(18) 0.016(4) Uiso 1 1 d . . .
C4 C 0.49420(18) 0.92035(15) 0.33798(17) 0.0228(3) Uani 1 1 d . . .
H4A H 0.4842 0.8782 0.2470 0.034 Uiso 1 1 calc R . .
H4B H 0.5109 1.0088 0.3248 0.034 Uiso 1 1 calc R . .
H4C H 0.4056 0.9093 0.3789 0.034 Uiso 1 1 calc R . .
O2 O 0.2500 0.84074(17) 0.7500 0.0383(5) Uani 1 2 d S . .
H2O H 0.229(2) 0.796(2) 0.813(2) 0.041(6) Uiso 1 1 d . . .


_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 N3 2.0133(13) . ?
Ni1 N3 2.0133(13) 2_656 ?
Ni1 N1 2.1348(13) 2_656 ?
Ni1 N1 2.1348(13) . ?
Ni1 N4 2.1494(13) 2_656 ?
Ni1 N4 2.1494(13) . ?
O1 C5 1.2709(18) . ?
N1 C1 1.3301(19) . ?
N1 C2 1.373(2) . ?
N2 C1 1.358(2) . ?
N2 C3 1.378(2) . ?
N2 C4 1.467(2) . ?
N3 C5 1.3028(19) . ?
N3 C6 1.4508(19) . ?
N4 C7 1.4807(19) . ?
N4 H4NA 0.87(2) . ?
N4 H4NB 0.866(19) . ?
C2 C3 1.360(2) . ?
C2 H2 0.920(19) . ?
C3 H3 0.912(18) . ?
C1 C5 1.502(2) . ?
C6 C7 1.527(2) . ?
C6 H6A 0.979(18) . ?
C6 H6B 0.979(18) . ?
C7 H7A 0.978(17) . ?
C7 H7B 0.992(18) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
O2 H2O 0.81(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
N3 Ni1 N3 177.68(7) . 2_656 ?
N3 Ni1 N1 99.82(5) . 2_656 ?
N3 Ni1 N1 78.50(5) 2_656 2_656 ?
N3 Ni1 N1 78.50(5) . . ?
N3 Ni1 N1 99.82(5) 2_656 . ?
N1 Ni1 N1 89.02(7) 2_656 . ?
N3 Ni1 N4 101.30(5) . 2_656 ?
N3 Ni1 N4 80.27(5) 2_656 2_656 ?
N1 Ni1 N4 158.53(5) 2_656 2_656 ?
N1 Ni1 N4 91.41(5) . 2_656 ?
N3 Ni1 N4 80.27(5) . . ?
N3 Ni1 N4 101.30(5) 2_656 . ?
N1 Ni1 N4 91.41(5) 2_656 . ?
N1 Ni1 N4 158.53(5) . . ?
N4 Ni1 N4 95.90(7) 2_656 . ?
C1 N1 C2 106.14(13) . . ?
C1 N1 Ni1 109.51(9) . . ?
C2 N1 Ni1 144.00(10) . . ?
C1 N2 C3 106.97(13) . . ?
C1 N2 C4 128.53(13) . . ?
C3 N2 C4 124.46(13) . . ?
C5 N3 C6 120.75(12) . . ?
C5 N3 Ni1 120.07(10) . . ?
C6 N3 Ni1 116.88(9) . . ?
C7 N4 Ni1 106.45(9) . . ?
C7 N4 H4NA 110.2(13) . . ?
Ni1 N4 H4NA 118.5(13) . . ?
C7 N4 H4NB 110.7(11) . . ?
Ni1 N4 H4NB 102.3(12) . . ?
H4NA N4 H4NB 108.3(17) . . ?
C3 C2 N1 109.58(14) . . ?
C3 C2 H2 128.6(12) . . ?
N1 C2 H2 121.8(11) . . ?
C2 C3 N2 106.52(13) . . ?
C2 C3 H3 132.6(11) . . ?
N2 C3 H3 120.9(11) . . ?
N1 C1 N2 110.79(13) . . ?
N1 C1 C5 120.45(13) . . ?
N2 C1 C5 128.61(13) . . ?
O1 C5 N3 129.11(14) . . ?
O1 C5 C1 120.92(13) . . ?
N3 C5 C1 109.95(13) . . ?
N3 C6 C7 107.40(12) . . ?
N3 C6 H6A 111.9(10) . . ?
C7 C6 H6A 109.1(10) . . ?
N3 C6 H6B 109.8(10) . . ?
C7 C6 H6B 109.8(10) . . ?
H6A C6 H6B 108.8(14) . . ?
N4 C7 C6 109.09(12) . . ?
N4 C7 H7A 112.4(9) . . ?
C6 C7 H7A 111.5(10) . . ?
N4 C7 H7B 106.9(10) . . ?
C6 C7 H7B 109.6(10) . . ?
H7A C7 H7B 107.2(13) . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 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
N3 Ni1 N1 C1 5.91(9) . . . . ?
N3 Ni1 N1 C1 -172.47(9) 2_656 . . . ?
N1 Ni1 N1 C1 -94.31(10) 2_656 . . . ?
N4 Ni1 N1 C1 107.16(10) 2_656 . . . ?
N4 Ni1 N1 C1 -2.95(19) . . . . ?
N3 Ni1 N1 C2 177.64(18) . . . . ?
N3 Ni1 N1 C2 -0.74(18) 2_656 . . . ?
N1 Ni1 N1 C2 77.41(17) 2_656 . . . ?
N4 Ni1 N1 C2 -81.11(17) 2_656 . . . ?
N4 Ni1 N1 C2 168.77(15) . . . . ?
N1 Ni1 N3 C5 75.31(12) 2_656 . . . ?
N1 Ni1 N3 C5 -11.66(11) . . . . ?
N4 Ni1 N3 C5 -100.80(11) 2_656 . . . ?
N4 Ni1 N3 C5 165.06(12) . . . . ?
N1 Ni1 N3 C6 -87.62(11) 2_656 . . . ?
N1 Ni1 N3 C6 -174.58(11) . . . . ?
N4 Ni1 N3 C6 96.28(11) 2_656 . . . ?
N4 Ni1 N3 C6 2.14(10) . . . . ?
N3 Ni1 N4 C7 23.70(9) . . . . ?
N3 Ni1 N4 C7 -158.03(9) 2_656 . . . ?
N1 Ni1 N4 C7 123.42(10) 2_656 . . . ?
N1 Ni1 N4 C7 32.51(18) . . . . ?
N4 Ni1 N4 C7 -76.80(9) 2_656 . . . ?
C1 N1 C2 C3 -0.16(17) . . . . ?
Ni1 N1 C2 C3 -172.04(13) . . . . ?
N1 C2 C3 N2 0.17(17) . . . . ?
C1 N2 C3 C2 -0.12(17) . . . . ?
C4 N2 C3 C2 -177.99(14) . . . . ?
C2 N1 C1 N2 0.09(16) . . . . ?
Ni1 N1 C1 N2 175.04(9) . . . . ?
C2 N1 C1 C5 -175.83(13) . . . . ?
Ni1 N1 C1 C5 -0.88(16) . . . . ?
C3 N2 C1 N1 0.02(16) . . . . ?
C4 N2 C1 N1 177.78(13) . . . . ?
C3 N2 C1 C5 175.51(14) . . . . ?
C4 N2 C1 C5 -6.7(2) . . . . ?
C6 N3 C5 O1 -2.2(2) . . . . ?
Ni1 N3 C5 O1 -164.42(12) . . . . ?
C6 N3 C5 C1 175.94(12) . . . . ?
Ni1 N3 C5 C1 13.68(16) . . . . ?
N1 C1 C5 O1 170.40(13) . . . . ?
N2 C1 C5 O1 -4.7(2) . . . . ?
N1 C1 C5 N3 -7.89(19) . . . . ?
N2 C1 C5 N3 177.00(14) . . . . ?
C5 N3 C6 C7 170.41(13) . . . . ?
Ni1 N3 C6 C7 -26.79(15) . . . . ?
Ni1 N4 C7 C6 -44.64(13) . . . . ?
N3 C6 C7 N4 47.05(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.08
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.059

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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 1855264'
_audit_update_record             
;
2018-07-11 deposited with the CCDC.
2018-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL
_chemical_name_systematic        
'1-methyl-N-(2-((4-oxopentan-2-ylidene)amino)ethyl)-1H-imidazole-2-carboxamido nickel(II)'
_chemical_name_common            
'1-methyl-N-(2-((4-oxopentan-2-ylidene)amino)ethyl)-1H-imidazole-2-carboxamido nickel(II)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H16 N4 Ni O2, 3(H2 O)'
_chemical_formula_sum            'C12 H22 N4 Ni O5'
_chemical_formula_weight         361.05

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8975(18)
_cell_length_b                   9.130(2)
_cell_length_c                   12.645(3)
_cell_angle_alpha                92.821(4)
_cell_angle_beta                 92.276(4)
_cell_angle_gamma                104.339(4)
_cell_volume                     769.4(3)
_cell_formula_units_Z            2

_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2910
_cell_measurement_theta_min      2.737
_cell_measurement_theta_max      25.028

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             380
_exptl_absorpt_coefficient_mu    1.290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.613
_exptl_absorpt_correction_T_max  0.871
_exptl_absorpt_process_details   
;
SADABS; Sheldrick, (1996).
;


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SMART APEX CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        <0.1
_diffrn_reflns_number            5732
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0434
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.90
_diffrn_reflns_theta_max         25.11
_reflns_number_total             2709
_reflns_number_gt                2235
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART 5.628 (Bruker, 2002)'
_computing_cell_refinement       'SAINT 6.36 (Bruker, 2002)'
_computing_data_reduction        'SAINT 6.36 (Bruker, 2002)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997) and Mercury (Macraeet al., 2006)'
_computing_publication_material  'PLATON (Spek, 2009)'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0184P)²+0.3443P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2709
_refine_ls_number_parameters     257
_refine_ls_number_restraints     28
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0280
_refine_ls_wR_factor_ref         0.0588
_refine_ls_wR_factor_gt          0.0579
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.74896(5) 0.52322(3) 0.49485(2) 0.01471(10) Uani 1 1 d . . .
O1 O 0.6299(2) 0.36496(16) 0.19386(12) 0.0181(4) Uani 1 1 d . . .
O2 O 0.8152(2) 0.66888(16) 0.60451(12) 0.0174(4) Uani 1 1 d . . .
N1 N 0.7455(3) 0.6697(2) 0.39345(14) 0.0150(4) Uani 1 1 d . . .
N2 N 0.6937(3) 0.7103(2) 0.22545(14) 0.0159(4) Uani 1 1 d . . .
N3 N 0.6848(3) 0.38770(19) 0.37738(14) 0.0146(4) Uani 1 1 d . . .
N4 N 0.7474(3) 0.3569(2) 0.57223(15) 0.0147(4) Uani 1 1 d . . .
C1 C 0.7066(3) 0.6060(3) 0.29510(18) 0.0151(5) Uani 1 1 d . . .
C2 C 0.7589(3) 0.8205(3) 0.38566(19) 0.0168(5) Uani 1 1 d . . .
H2 H 0.780(3) 0.885(3) 0.4449(18) 0.017(6) Uiso 1 1 d . . .
C3 C 0.7273(3) 0.8470(3) 0.28279(19) 0.0172(5) Uani 1 1 d . . .
H3 H 0.721(3) 0.937(3) 0.2498(17) 0.021 Uiso 1 1 d . . .
C4 C 0.6474(4) 0.6860(3) 0.11052(18) 0.0232(6) Uani 1 1 d . . .
H4A H 0.7724 0.7006 0.0736 0.035 Uiso 1 1 calc R . .
H4B H 0.5736 0.7586 0.0872 0.035 Uiso 1 1 calc R . .
H4C H 0.5654 0.5826 0.0941 0.035 Uiso 1 1 calc R . .
C5 C 0.6704(3) 0.4380(2) 0.28224(18) 0.0154(5) Uani 1 1 d . . .
C6 C 0.6332(4) 0.2281(3) 0.39889(19) 0.0173(5) Uani 1 1 d . . .
H6A H 0.677(4) 0.170(3) 0.3440(19) 0.028(7) Uiso 1 1 d . . .
H6B H 0.486(3) 0.191(2) 0.3999(16) 0.011(6) Uiso 1 1 d . . .
C7 C 0.7326(4) 0.2154(3) 0.50624(19) 0.0171(5) Uani 1 1 d . . .
H7A H 0.655(3) 0.130(3) 0.5409(17) 0.020(6) Uiso 1 1 d . . .
H7B H 0.872(3) 0.202(2) 0.4973(16) 0.012(6) Uiso 1 1 d . . .
C8 C 0.7787(3) 0.3601(3) 0.67541(18) 0.0161(5) Uani 1 1 d . . .
C9 C 0.8114(3) 0.4970(3) 0.73946(19) 0.0177(5) Uani 1 1 d . . .
H9 H 0.825(3) 0.490(2) 0.8113(18) 0.016(6) Uiso 1 1 d . . .
C10 C 0.8293(3) 0.6380(3) 0.70315(18) 0.0164(5) Uani 1 1 d . . .
C11 C 0.7868(3) 0.2189(3) 0.73030(18) 0.0196(5) Uani 1 1 d . . .
H11A H 0.6559 0.1457 0.7210 0.029 Uiso 1 1 calc R . .
H11B H 0.8206 0.2445 0.8061 0.029 Uiso 1 1 calc R . .
H11C H 0.8891 0.1746 0.6995 0.029 Uiso 1 1 calc R . .
C12 C 0.8753(4) 0.7755(3) 0.78027(18) 0.0226(6) Uani 1 1 d . . .
H12A H 1.0194 0.8234 0.7831 0.034 Uiso 1 1 calc R . .
H12B H 0.8352 0.7445 0.8509 0.034 Uiso 1 1 calc R . .
H12C H 0.8012 0.8479 0.7568 0.034 Uiso 1 1 calc R . .
O3 O 0.5214(3) 0.0646(2) 0.13324(15) 0.0251(4) Uani 1 1 d D . .
H3OA H 0.548(4) 0.150(2) 0.154(2) 0.039(9) Uiso 1 1 d D . .
H3OB H 0.604(3) 0.063(3) 0.0925(19) 0.036(9) Uiso 1 1 d D . .
O4 O 0.8498(3) 0.3708(2) 0.01173(16) 0.0287(4) Uani 1 1 d D . .
H4OA H 0.792(4) 0.377(3) 0.0647(17) 0.044(10) Uiso 1 1 d D . .
H4OB H 0.943(8) 0.440(6) 0.006(6) 0.067 Uiso 0.50 1 d PD . .
H4OC H 0.855(10) 0.288(3) -0.004(5) 0.067 Uiso 0.50 1 d PD . .
O5 O 0.8314(3) 0.0610(2) 0.98868(16) 0.0272(4) Uani 1 1 d D . .
H5OA H 0.752(4) 0.024(3) 0.9435(19) 0.050(10) Uiso 1 1 d D . .
H5OB H 0.932(7) 0.036(9) 0.990(6) 0.075 Uiso 0.50 1 d PD . .
H5OC H 0.870(10) 0.148(2) 0.986(6) 0.075 Uiso 0.50 1 d PD . .


_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 O2 1.8350(15) . no
Ni1 N4 1.8444(19) . no
Ni1 N3 1.8517(18) . no
Ni1 N1 1.9013(19) . no
O1 C5 1.257(3) . no
O2 C10 1.297(3) . no
N1 C1 1.335(3) . no
N1 C2 1.366(3) . no
N2 C1 1.345(3) . no
N2 C3 1.375(3) . no
N2 C4 1.470(3) . no
N3 C5 1.317(3) . no
N3 C6 1.454(3) . no
N4 C8 1.312(3) . no
N4 C7 1.483(3) . no
C1 C5 1.492(3) . no
C2 C3 1.354(3) . no
C2 H2 0.91(2) . no
C3 H3 0.95(2) . no
C4 H4A 0.9800 . no
C4 H4B 0.9800 . no
C4 H4C 0.9800 . no
C6 C7 1.519(3) . no
C6 H6A 0.96(2) . no
C6 H6B 0.99(2) . no
C7 H7A 0.97(2) . no
C7 H7B 1.01(2) . no
C8 C9 1.420(3) . no
C8 C11 1.506(3) . no
C9 C10 1.367(3) . no
C9 H9 0.92(2) . no
C10 C12 1.511(3) . no
C11 H11A 0.9800 . no
C11 H11B 0.9800 . no
C11 H11C 0.9800 . no
C12 H12A 0.9800 . no
C12 H12B 0.9800 . no
C12 H12C 0.9800 . no
O3 H3OA 0.787(16) . no
O3 H3OB 0.785(16) . no
O4 H4OA 0.798(16) . no
O4 H4OB 0.791(18) . no
O4 H4OC 0.781(18) . no
O5 H5OA 0.778(16) . no
O5 H5OB 0.782(18) . no
O5 H5OC 0.777(19) . no

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
O2 Ni1 N4 97.97(8) . . no
O2 Ni1 N3 175.76(8) . . no
N4 Ni1 N3 86.22(8) . . no
O2 Ni1 N1 92.25(8) . . no
N4 Ni1 N1 169.67(8) . . no
N3 Ni1 N1 83.55(8) . . no
C10 O2 Ni1 123.36(14) . . no
C1 N1 C2 106.35(19) . . no
C1 N1 Ni1 111.72(15) . . no
C2 N1 Ni1 141.81(16) . . no
C1 N2 C3 106.74(19) . . no
C1 N2 C4 127.74(19) . . no
C3 N2 C4 125.50(19) . . no
C5 N3 C6 123.76(19) . . no
C5 N3 Ni1 119.91(15) . . no
C6 N3 Ni1 116.03(14) . . no
C8 N4 C7 120.34(19) . . no
C8 N4 Ni1 125.34(16) . . no
C7 N4 Ni1 113.91(14) . . no
N1 C1 N2 110.72(19) . . no
N1 C1 C5 117.2(2) . . no
N2 C1 C5 131.9(2) . . no
C3 C2 N1 109.0(2) . . no
C3 C2 H2 130.1(14) . . no
N1 C2 H2 120.8(14) . . no
C2 C3 N2 107.2(2) . . no
C2 C3 H3 131.3(14) . . no
N2 C3 H3 121.5(14) . . no
N2 C4 H4A 109.5 . . no
N2 C4 H4B 109.5 . . no
H4A C4 H4B 109.5 . . no
N2 C4 H4C 109.5 . . no
H4A C4 H4C 109.5 . . no
H4B C4 H4C 109.5 . . no
O1 C5 N3 129.3(2) . . no
O1 C5 C1 123.1(2) . . no
N3 C5 C1 107.55(19) . . no
N3 C6 C7 106.91(19) . . no
N3 C6 H6A 110.3(14) . . no
C7 C6 H6A 111.9(15) . . no
N3 C6 H6B 109.5(12) . . no
C7 C6 H6B 110.8(12) . . no
H6A C6 H6B 107.5(18) . . no
N4 C7 C6 108.83(18) . . no
N4 C7 H7A 109.9(13) . . no
C6 C7 H7A 110.2(14) . . no
N4 C7 H7B 108.8(12) . . no
C6 C7 H7B 110.1(12) . . no
H7A C7 H7B 109.0(18) . . no
N4 C8 C9 121.5(2) . . no
N4 C8 C11 121.1(2) . . no
C9 C8 C11 117.3(2) . . no
C10 C9 C8 125.7(2) . . no
C10 C9 H9 117.4(14) . . no
C8 C9 H9 116.8(14) . . no
O2 C10 C9 125.7(2) . . no
O2 C10 C12 114.2(2) . . no
C9 C10 C12 120.1(2) . . no
C8 C11 H11A 109.5 . . no
C8 C11 H11B 109.5 . . no
H11A C11 H11B 109.5 . . no
C8 C11 H11C 109.5 . . no
H11A C11 H11C 109.5 . . no
H11B C11 H11C 109.5 . . no
C10 C12 H12A 109.5 . . no
C10 C12 H12B 109.5 . . no
H12A C12 H12B 109.5 . . no
C10 C12 H12C 109.5 . . no
H12A C12 H12C 109.5 . . no
H12B C12 H12C 109.5 . . no
H3OA O3 H3OB 103(3) . . no
H4OA O4 H4OB 113(6) . . no
H4OA O4 H4OC 113(6) . . no
H4OB O4 H4OC 121(8) . . no
H5OA O5 H5OB 117(6) . . no
H5OA O5 H5OC 113(6) . . no
H5OB O5 H5OC 101(8) . . no

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
N4 Ni1 O2 C10 -5.93(17) . . . . no
N1 Ni1 O2 C10 175.58(17) . . . . no
O2 Ni1 N1 C1 177.87(15) . . . . no
N4 Ni1 N1 C1 6.2(5) . . . . no
N3 Ni1 N1 C1 -1.58(15) . . . . no
O2 Ni1 N1 C2 -7.0(2) . . . . no
N4 Ni1 N1 C2 -178.6(4) . . . . no
N3 Ni1 N1 C2 173.5(3) . . . . no
N4 Ni1 N3 C5 -176.55(17) . . . . no
N1 Ni1 N3 C5 2.05(16) . . . . no
N4 Ni1 N3 C6 9.45(17) . . . . no
N1 Ni1 N3 C6 -171.95(17) . . . . no
O2 Ni1 N4 C8 2.57(19) . . . . no
N3 Ni1 N4 C8 -178.09(19) . . . . no
N1 Ni1 N4 C8 174.1(4) . . . . no
O2 Ni1 N4 C7 -170.01(15) . . . . no
N3 Ni1 N4 C7 9.33(16) . . . . no
N1 Ni1 N4 C7 1.6(5) . . . . no
C2 N1 C1 N2 -0.4(2) . . . . no
Ni1 N1 C1 N2 176.51(14) . . . . no
C2 N1 C1 C5 -175.81(18) . . . . no
Ni1 N1 C1 C5 1.1(2) . . . . no
C3 N2 C1 N1 0.4(3) . . . . no
C4 N2 C1 N1 -178.1(2) . . . . no
C3 N2 C1 C5 174.9(2) . . . . no
C4 N2 C1 C5 -3.5(4) . . . . no
C1 N1 C2 C3 0.2(2) . . . . no
Ni1 N1 C2 C3 -175.08(19) . . . . no
N1 C2 C3 N2 0.0(3) . . . . no
C1 N2 C3 C2 -0.2(2) . . . . no
C4 N2 C3 C2 178.3(2) . . . . no
C6 N3 C5 O1 -6.9(4) . . . . no
Ni1 N3 C5 O1 179.57(18) . . . . no
C6 N3 C5 C1 171.7(2) . . . . no
Ni1 N3 C5 C1 -1.9(2) . . . . no
N1 C1 C5 O1 179.1(2) . . . . no
N2 C1 C5 O1 4.8(4) . . . . no
N1 C1 C5 N3 0.4(3) . . . . no
N2 C1 C5 N3 -173.9(2) . . . . no
C5 N3 C6 C7 161.7(2) . . . . no
Ni1 N3 C6 C7 -24.5(2) . . . . no
C8 N4 C7 C6 162.3(2) . . . . no
Ni1 N4 C7 C6 -24.7(2) . . . . no
N3 C6 C7 N4 30.0(3) . . . . no
C7 N4 C8 C9 174.3(2) . . . . no
Ni1 N4 C8 C9 2.1(3) . . . . no
C7 N4 C8 C11 -4.1(3) . . . . no
Ni1 N4 C8 C11 -176.19(15) . . . . no
N4 C8 C9 C10 -5.2(4) . . . . no
C11 C8 C9 C10 173.2(2) . . . . no
Ni1 O2 C10 C9 4.8(3) . . . . no
Ni1 O2 C10 C12 -177.02(14) . . . . no
C8 C9 C10 O2 1.4(4) . . . . no
C8 C9 C10 C12 -176.6(2) . . . . no

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.11
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.072

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone, water'
####################################################################### 
# 
# 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 1855266'
_audit_update_record             
;
2018-07-11 deposited with the CCDC.
2018-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL
_chemical_name_systematic        
'1-methyl-(methyl-(3-(2-ethyl)imino)butanoate) -1H-imidazole-2-carboxamido nickel(II)'
_chemical_name_common            
'1-methyl-(methyl-(3-(2-ethyl)imino)butanoate) -1H-imidazole-2-carboxamido nickel(II)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H16 N4 Ni O3, H2 O'
_chemical_formula_sum            'C12 H18 N4 Ni O4'
_chemical_formula_weight         341.01

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc '


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

_cell_length_a                   9.2792(6)
_cell_length_b                   13.6005(8)
_cell_length_c                   21.7240(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.3700(10)
_cell_angle_gamma                90.00
_cell_volume                     2729.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4410
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      25.003

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.242
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.030
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1424
_exptl_absorpt_coefficient_mu    1.444
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.754
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   
;
SADABS; Sheldrick, (1996).
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SMART APEX CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        <0.1
_diffrn_reflns_number            19823
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_sigmaI/netI    0.0499
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         25.12
_reflns_number_total             4861
_reflns_number_gt                3728
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART 5.628 (Bruker, 2002)'
_computing_cell_refinement       'SAINT 6.36 (Bruker, 2002)'
_computing_data_reduction        'SAINT 6.36 (Bruker, 2002)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997) and Mercury (Macraeet al., 2006)'
_computing_publication_material  'PLATON (Spek, 2009)'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0158P)²+0.2835P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4861
_refine_ls_number_parameters     452
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0628
_refine_ls_wR_factor_gt          0.0593
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.32701(4) 0.58195(3) 0.211669(17) 0.01827(11) Uani 1 1 d . . .
O1 O 0.4729(2) 0.58158(14) 0.38952(8) 0.0220(5) Uani 1 1 d . . .
O2 O 0.1890(2) 0.58093(14) 0.14397(8) 0.0215(5) Uani 1 1 d . . .
O3 O 0.1119(2) 0.58853(15) 0.04275(9) 0.0314(5) Uani 1 1 d . . .
N1 N 0.1849(2) 0.57483(16) 0.26832(10) 0.0174(5) Uani 1 1 d . . .
N2 N 0.1400(2) 0.57073(16) 0.36592(10) 0.0190(6) Uani 1 1 d . . .
N3 N 0.4542(2) 0.58103(16) 0.28205(10) 0.0181(5) Uani 1 1 d . . .
N4 N 0.4887(2) 0.58603(16) 0.16851(10) 0.0208(6) Uani 1 1 d . . .
C1 C 0.2438(3) 0.57443(19) 0.32660(13) 0.0173(7) Uani 1 1 d . . .
C2 C 0.0374(3) 0.5713(2) 0.27085(14) 0.0196(7) Uani 1 1 d . . .
H2 H -0.024(3) 0.5689(19) 0.2348(12) 0.023 Uiso 1 1 d . . .
C3 C 0.0090(3) 0.5685(2) 0.33048(14) 0.0207(7) Uani 1 1 d . . .
H3 H -0.075(3) 0.5627(19) 0.3508(12) 0.025 Uiso 1 1 d . . .
C4 C 0.1597(3) 0.5718(2) 0.43349(12) 0.0259(7) Uani 1 1 d . . .
H4A H 0.2498 0.5376 0.4476 0.039 Uiso 1 1 calc R . .
H4B H 0.0779 0.5385 0.4500 0.039 Uiso 1 1 calc R . .
H4C H 0.1647 0.6399 0.4482 0.039 Uiso 1 1 calc R . .
C5 C 0.4047(3) 0.57958(19) 0.33703(14) 0.0186(7) Uani 1 1 d . . .
C6 C 0.6065(3) 0.5951(2) 0.27429(14) 0.0206(7) Uani 1 1 d . . .
H6A H 0.669(3) 0.554(2) 0.3015(12) 0.024(8) Uiso 1 1 d . . .
H6B H 0.633(3) 0.664(2) 0.2842(12) 0.022(8) Uiso 1 1 d . . .
C7 C 0.6275(3) 0.5739(2) 0.20729(14) 0.0217(7) Uani 1 1 d . . .
H7A H 0.706(3) 0.618(2) 0.1919(12) 0.026 Uiso 1 1 d . . .
H7B H 0.661(3) 0.507(2) 0.2045(12) 0.026 Uiso 1 1 d . . .
C8 C 0.4869(3) 0.5879(2) 0.10796(13) 0.0213(7) Uani 1 1 d . . .
C9 C 0.3587(3) 0.5916(2) 0.06873(14) 0.0244(7) Uani 1 1 d . . .
H9 H 0.364(3) 0.5964(19) 0.0254(12) 0.019(8) Uiso 1 1 d . . .
C10 C 0.2222(3) 0.5875(2) 0.08823(14) 0.0232(7) Uani 1 1 d . . .
C11 C 0.6266(3) 0.5855(2) 0.07743(13) 0.0272(8) Uani 1 1 d . . .
H11A H 0.6840 0.6441 0.0894 0.041 Uiso 1 1 calc R . .
H11B H 0.6049 0.5844 0.0324 0.041 Uiso 1 1 calc R . .
H11C H 0.6816 0.5265 0.0907 0.041 Uiso 1 1 calc R . .
C12 C -0.0305(3) 0.5859(2) 0.06066(14) 0.0319(8) Uani 1 1 d . . .
H12A H -0.0407 0.5296 0.0881 0.048 Uiso 1 1 calc R . .
H12B H -0.0994 0.5795 0.0238 0.048 Uiso 1 1 calc R . .
H12C H -0.0501 0.6468 0.0825 0.048 Uiso 1 1 calc R . .
Ni2 Ni 0.29953(4) 0.81885(3) 0.254582(17) 0.01685(11) Uani 1 1 d . . .
O4 O 0.1697(2) 0.84848(14) 0.07616(8) 0.0231(5) Uani 1 1 d . . .
O5 O 0.42956(19) 0.81747(13) 0.32466(8) 0.0191(5) Uani 1 1 d . . .
O6 O 0.4972(2) 0.82289(14) 0.42642(8) 0.0241(5) Uani 1 1 d . . .
N5 N 0.4484(2) 0.83162(15) 0.20088(10) 0.0163(5) Uani 1 1 d . . .
N6 N 0.5015(2) 0.84194(16) 0.10456(10) 0.0176(5) Uani 1 1 d . . .
N7 N 0.1790(2) 0.82374(16) 0.18240(10) 0.0176(5) Uani 1 1 d . . .
N8 N 0.1321(2) 0.81554(16) 0.29434(10) 0.0176(5) Uani 1 1 d . . .
C13 C 0.3949(3) 0.83805(19) 0.14191(13) 0.0173(7) Uani 1 1 d . . .
C14 C 0.5961(3) 0.8335(2) 0.20073(14) 0.0187(7) Uani 1 1 d . . .
H14 H 0.657(3) 0.8298(18) 0.2372(12) 0.016(8) Uiso 1 1 d . . .
C15 C 0.6302(3) 0.8394(2) 0.14179(14) 0.0195(7) Uani 1 1 d . . .
H15 H 0.718(3) 0.8411(19) 0.1236(12) 0.023 Uiso 1 1 d . . .
C16 C 0.4885(3) 0.8498(2) 0.03708(12) 0.0246(7) Uani 1 1 d . . .
H16A H 0.4056 0.8108 0.0198 0.037 Uiso 1 1 calc R . .
H16B H 0.5771 0.8251 0.0212 0.037 Uiso 1 1 calc R . .
H16C H 0.4740 0.9188 0.0251 0.037 Uiso 1 1 calc R . .
C17 C 0.2344(3) 0.83687(19) 0.12920(14) 0.0184(7) Uani 1 1 d . . .
C18 C 0.0254(3) 0.8078(3) 0.18682(14) 0.0225(7) Uani 1 1 d . . .
H18A H -0.002(3) 0.7382(19) 0.1712(11) 0.019(7) Uiso 1 1 d . . .
H18B H -0.029(3) 0.8532(19) 0.1621(12) 0.021(8) Uiso 1 1 d . . .
C19 C -0.0051(3) 0.8204(2) 0.25391(14) 0.0208(7) Uani 1 1 d . . .
H19A H -0.052(3) 0.8834(19) 0.2595(11) 0.013(7) Uiso 1 1 d . . .
H19B H -0.073(3) 0.7709(19) 0.2643(11) 0.018(8) Uiso 1 1 d . . .
C20 C 0.1271(3) 0.8184(2) 0.35499(13) 0.0201(7) Uani 1 1 d . . .
C21 C 0.2514(3) 0.8199(2) 0.39657(14) 0.0214(7) Uani 1 1 d . . .
H21 H 0.238(3) 0.8187(18) 0.4404(12) 0.018(7) Uiso 1 1 d . . .
C22 C 0.3917(3) 0.8193(2) 0.37933(13) 0.0201(7) Uani 1 1 d . . .
C23 C -0.0167(3) 0.8213(2) 0.38177(13) 0.0260(7) Uani 1 1 d . . .
H23A H -0.0706 0.8797 0.3665 0.039 Uiso 1 1 calc R . .
H23B H -0.0009 0.8239 0.4270 0.039 Uiso 1 1 calc R . .
H23C H -0.0723 0.7622 0.3692 0.039 Uiso 1 1 calc R . .
C24 C 0.6432(3) 0.8186(2) 0.40953(13) 0.0253(7) Uani 1 1 d . . .
H24A H 0.6561 0.7585 0.3858 0.038 Uiso 1 1 calc R . .
H24B H 0.7108 0.8183 0.4470 0.038 Uiso 1 1 calc R . .
H24C H 0.6621 0.8761 0.3843 0.038 Uiso 1 1 calc R . .
O7 O 0.7620(3) 0.55899(19) 0.43264(11) 0.0257(6) Uani 1 1 d . . .
H7OA H 0.684(3) 0.567(2) 0.4187(14) 0.029(11) Uiso 1 1 d . . .
H7OB H 0.779(4) 0.503(3) 0.4354(17) 0.059(15) Uiso 1 1 d . . .
O8 O 0.8686(3) 0.68020(18) 0.53514(12) 0.0311(6) Uani 1 1 d . . .
H8OA H 0.844(3) 0.648(2) 0.5044(15) 0.038(11) Uiso 1 1 d . . .
H8OB H 0.953(4) 0.677(2) 0.5411(15) 0.041(12) Uiso 1 1 d . . .


_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 N3 1.842(2) . no
Ni1 N4 1.843(2) . no
Ni1 O2 1.8578(18) . no
Ni1 N1 1.889(2) . no
O1 C5 1.252(3) . no
O2 C10 1.280(3) . no
O3 C10 1.354(3) . no
O3 C12 1.413(3) . no
N1 C1 1.331(3) . no
N1 C2 1.375(3) . no
N2 C1 1.347(3) . no
N2 C3 1.377(3) . no
N2 C4 1.462(3) . no
N3 C5 1.319(3) . no
N3 C6 1.452(4) . no
N4 C8 1.314(3) . no
N4 C7 1.481(3) . no
C1 C5 1.490(4) . no
C2 C3 1.347(4) . no
C2 H2 0.92(3) . no
C3 H3 0.94(3) . no
C4 H4A 0.9800 . no
C4 H4B 0.9800 . no
C4 H4C 0.9800 . no
C6 C7 1.514(4) . no
C6 H6A 0.97(3) . no
C6 H6B 0.99(3) . no
C7 H7A 1.02(3) . no
C7 H7B 0.96(3) . no
C8 C9 1.398(4) . no
C8 C11 1.511(4) . no
C9 C10 1.374(4) . no
C9 H9 0.95(3) . no
C11 H11A 0.9800 . no
C11 H11B 0.9800 . no
C11 H11C 0.9800 . no
C12 H12A 0.9800 . no
C12 H12B 0.9800 . no
C12 H12C 0.9800 . no
Ni2 N7 1.840(2) . no
Ni2 N8 1.847(2) . no
Ni2 O5 1.8521(18) . no
Ni2 N5 1.898(2) . no
O4 C17 1.258(3) . no
O5 C22 1.270(3) . no
O6 C22 1.349(3) . no
O6 C24 1.438(3) . no
N5 C13 1.333(3) . no
N5 C14 1.371(3) . no
N6 C13 1.338(3) . no
N6 C15 1.378(3) . no
N6 C16 1.463(3) . no
N7 C17 1.320(3) . no
N7 C18 1.453(4) . no
N8 C20 1.323(3) . no
N8 C19 1.479(3) . no
C13 C17 1.490(4) . no
C14 C15 1.350(4) . no
C14 H14 0.93(2) . no
C15 H15 0.94(3) . no
C16 H16A 0.9800 . no
C16 H16B 0.9800 . no
C16 H16C 0.9800 . no
C18 C19 1.520(4) . no
C18 H18A 1.03(3) . no
C18 H18B 0.94(3) . no
C19 H19A 0.97(2) . no
C19 H19B 0.96(3) . no
C20 C21 1.397(4) . no
C20 C23 1.505(4) . no
C21 C22 1.388(4) . no
C21 H21 0.97(2) . no
C23 H23A 0.9800 . no
C23 H23B 0.9800 . no
C23 H23C 0.9800 . no
C24 H24A 0.9800 . no
C24 H24B 0.9800 . no
C24 H24C 0.9800 . no
O7 H7OA 0.76(3) . no
O7 H7OB 0.78(4) . no
O8 H8OA 0.82(3) . no
O8 H8OB 0.78(3) . no

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
N3 Ni1 N4 86.21(10) . . no
N3 Ni1 O2 176.19(10) . . no
N4 Ni1 O2 97.53(9) . . no
N3 Ni1 N1 83.74(10) . . no
N4 Ni1 N1 169.88(10) . . no
O2 Ni1 N1 92.50(9) . . no
C10 O2 Ni1 122.61(19) . . no
C10 O3 C12 117.5(2) . . no
C1 N1 C2 106.5(2) . . no
C1 N1 Ni1 111.71(18) . . no
C2 N1 Ni1 141.8(2) . . no
C1 N2 C3 107.0(2) . . no
C1 N2 C4 127.3(2) . . no
C3 N2 C4 125.6(2) . . no
C5 N3 C6 122.2(2) . . no
C5 N3 Ni1 120.09(19) . . no
C6 N3 Ni1 117.24(18) . . no
C8 N4 C7 120.0(3) . . no
C8 N4 Ni1 125.1(2) . . no
C7 N4 Ni1 114.42(18) . . no
N1 C1 N2 110.4(2) . . no
N1 C1 C5 117.5(3) . . no
N2 C1 C5 132.1(2) . . no
C3 C2 N1 109.0(3) . . no
C3 C2 H2 130.7(17) . . no
N1 C2 H2 120.3(17) . . no
C2 C3 N2 107.2(3) . . no
C2 C3 H3 134.7(17) . . no
N2 C3 H3 118.1(17) . . no
N2 C4 H4A 109.5 . . no
N2 C4 H4B 109.5 . . no
H4A C4 H4B 109.5 . . no
N2 C4 H4C 109.5 . . no
H4A C4 H4C 109.5 . . no
H4B C4 H4C 109.5 . . no
O1 C5 N3 129.4(3) . . no
O1 C5 C1 123.6(3) . . no
N3 C5 C1 107.0(2) . . no
N3 C6 C7 107.5(2) . . no
N3 C6 H6A 112.7(16) . . no
C7 C6 H6A 110.7(16) . . no
N3 C6 H6B 108.9(15) . . no
C7 C6 H6B 109.7(15) . . no
H6A C6 H6B 107(2) . . no
N4 C7 C6 110.0(2) . . no
N4 C7 H7A 110.8(15) . . no
C6 C7 H7A 111.1(15) . . no
N4 C7 H7B 109.5(16) . . no
C6 C7 H7B 108.0(16) . . no
H7A C7 H7B 107(2) . . no
N4 C8 C9 122.8(3) . . no
N4 C8 C11 120.5(3) . . no
C9 C8 C11 116.7(3) . . no
C10 C9 C8 124.5(3) . . no
C10 C9 H9 116.4(16) . . no
C8 C9 H9 119.0(16) . . no
O2 C10 O3 117.3(3) . . no
O2 C10 C9 127.2(3) . . no
O3 C10 C9 115.5(3) . . no
C8 C11 H11A 109.5 . . no
C8 C11 H11B 109.5 . . no
H11A C11 H11B 109.5 . . no
C8 C11 H11C 109.5 . . no
H11A C11 H11C 109.5 . . no
H11B C11 H11C 109.5 . . no
O3 C12 H12A 109.5 . . no
O3 C12 H12B 109.5 . . no
H12A C12 H12B 109.5 . . no
O3 C12 H12C 109.5 . . no
H12A C12 H12C 109.5 . . no
H12B C12 H12C 109.5 . . no
N7 Ni2 N8 85.91(10) . . no
N7 Ni2 O5 176.50(10) . . no
N8 Ni2 O5 97.30(9) . . no
N7 Ni2 N5 83.81(10) . . no
N8 Ni2 N5 169.14(10) . . no
O5 Ni2 N5 92.90(9) . . no
C22 O5 Ni2 123.54(18) . . no
C22 O6 C24 116.1(2) . . no
C13 N5 C14 106.2(2) . . no
C13 N5 Ni2 111.73(18) . . no
C14 N5 Ni2 142.0(2) . . no
C13 N6 C15 107.0(2) . . no
C13 N6 C16 127.9(2) . . no
C15 N6 C16 125.1(2) . . no
C17 N7 C18 122.8(2) . . no
C17 N7 Ni2 119.70(19) . . no
C18 N7 Ni2 117.38(19) . . no
C20 N8 C19 118.8(2) . . no
C20 N8 Ni2 125.1(2) . . no
C19 N8 Ni2 115.86(17) . . no
N5 C13 N6 110.9(2) . . no
N5 C13 C17 116.9(3) . . no
N6 C13 C17 132.2(3) . . no
C15 C14 N5 109.0(3) . . no
C15 C14 H14 129.2(16) . . no
N5 C14 H14 121.8(16) . . no
C14 C15 N6 106.9(3) . . no
C14 C15 H15 133.6(17) . . no
N6 C15 H15 119.5(16) . . no
N6 C16 H16A 109.5 . . no
N6 C16 H16B 109.5 . . no
H16A C16 H16B 109.5 . . no
N6 C16 H16C 109.5 . . no
H16A C16 H16C 109.5 . . no
H16B C16 H16C 109.5 . . no
O4 C17 N7 128.8(3) . . no
O4 C17 C13 123.5(3) . . no
N7 C17 C13 107.7(2) . . no
N7 C18 C19 108.6(2) . . no
N7 C18 H18A 109.1(14) . . no
C19 C18 H18A 111.0(14) . . no
N7 C18 H18B 110.3(17) . . no
C19 C18 H18B 109.6(16) . . no
H18A C18 H18B 108(2) . . no
N8 C19 C18 109.7(2) . . no
N8 C19 H19A 109.5(15) . . no
C18 C19 H19A 110.1(15) . . no
N8 C19 H19B 112.2(15) . . no
C18 C19 H19B 109.3(15) . . no
H19A C19 H19B 106(2) . . no
N8 C20 C21 122.7(3) . . no
N8 C20 C23 120.0(3) . . no
C21 C20 C23 117.3(3) . . no
C22 C21 C20 124.3(3) . . no
C22 C21 H21 118.2(15) . . no
C20 C21 H21 117.4(15) . . no
O5 C22 O6 117.7(3) . . no
O5 C22 C21 127.0(3) . . no
O6 C22 C21 115.3(3) . . no
C20 C23 H23A 109.5 . . no
C20 C23 H23B 109.5 . . no
H23A C23 H23B 109.5 . . no
C20 C23 H23C 109.5 . . no
H23A C23 H23C 109.5 . . no
H23B C23 H23C 109.5 . . no
O6 C24 H24A 109.5 . . no
O6 C24 H24B 109.5 . . no
H24A C24 H24B 109.5 . . no
O6 C24 H24C 109.5 . . no
H24A C24 H24C 109.5 . . no
H24B C24 H24C 109.5 . . no
H7OA O7 H7OB 111(4) . . no
H8OA O8 H8OB 108(3) . . no

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
N4 Ni1 O2 C10 -3.3(2) . . . . no
N1 Ni1 O2 C10 177.9(2) . . . . no
N3 Ni1 N1 C1 1.00(19) . . . . no
N4 Ni1 N1 C1 7.6(7) . . . . no
O2 Ni1 N1 C1 -179.64(18) . . . . no
N3 Ni1 N1 C2 179.6(3) . . . . no
N4 Ni1 N1 C2 -173.8(5) . . . . no
O2 Ni1 N1 C2 -1.0(3) . . . . no
N4 Ni1 N3 C5 179.0(2) . . . . no
N1 Ni1 N3 C5 -2.2(2) . . . . no
N4 Ni1 N3 C6 7.0(2) . . . . no
N1 Ni1 N3 C6 -174.2(2) . . . . no
N3 Ni1 N4 C8 179.7(2) . . . . no
O2 Ni1 N4 C8 0.4(2) . . . . no
N1 Ni1 N4 C8 173.1(5) . . . . no
N3 Ni1 N4 C7 7.29(19) . . . . no
O2 Ni1 N4 C7 -172.00(19) . . . . no
N1 Ni1 N4 C7 0.7(7) . . . . no
C2 N1 C1 N2 0.0(3) . . . . no
Ni1 N1 C1 N2 179.12(17) . . . . no
C2 N1 C1 C5 -179.0(2) . . . . no
Ni1 N1 C1 C5 0.1(3) . . . . no
C3 N2 C1 N1 0.1(3) . . . . no
C4 N2 C1 N1 -178.2(2) . . . . no
C3 N2 C1 C5 179.0(3) . . . . no
C4 N2 C1 C5 0.6(5) . . . . no
C1 N1 C2 C3 -0.1(3) . . . . no
Ni1 N1 C2 C3 -178.8(2) . . . . no
N1 C2 C3 N2 0.2(3) . . . . no
C1 N2 C3 C2 -0.2(3) . . . . no
C4 N2 C3 C2 178.2(2) . . . . no
C6 N3 C5 O1 -6.1(5) . . . . no
Ni1 N3 C5 O1 -177.7(2) . . . . no
C6 N3 C5 C1 174.1(2) . . . . no
Ni1 N3 C5 C1 2.5(3) . . . . no
N1 C1 C5 O1 178.6(2) . . . . no
N2 C1 C5 O1 -0.2(5) . . . . no
N1 C1 C5 N3 -1.6(3) . . . . no
N2 C1 C5 N3 179.6(3) . . . . no
C5 N3 C6 C7 169.7(3) . . . . no
Ni1 N3 C6 C7 -18.5(3) . . . . no
C8 N4 C7 C6 168.2(3) . . . . no
Ni1 N4 C7 C6 -19.0(3) . . . . no
N3 C6 C7 N4 22.7(3) . . . . no
C7 N4 C8 C9 175.0(3) . . . . no
Ni1 N4 C8 C9 3.0(4) . . . . no
C7 N4 C8 C11 -4.6(4) . . . . no
Ni1 N4 C8 C11 -176.6(2) . . . . no
N4 C8 C9 C10 -4.2(5) . . . . no
C11 C8 C9 C10 175.4(3) . . . . no
Ni1 O2 C10 O3 -178.31(17) . . . . no
Ni1 O2 C10 C9 3.2(4) . . . . no
C12 O3 C10 O2 2.3(4) . . . . no
C12 O3 C10 C9 -179.1(3) . . . . no
C8 C9 C10 O2 0.8(5) . . . . no
C8 C9 C10 O3 -177.7(3) . . . . no
N8 Ni2 O5 C22 -3.2(2) . . . . no
N5 Ni2 O5 C22 173.1(2) . . . . no
N7 Ni2 N5 C13 0.44(18) . . . . no
N8 Ni2 N5 C13 -18.5(6) . . . . no
O5 Ni2 N5 C13 -178.36(18) . . . . no
N7 Ni2 N5 C14 -176.5(3) . . . . no
N8 Ni2 N5 C14 164.6(4) . . . . no
O5 Ni2 N5 C14 4.7(3) . . . . no
N8 Ni2 N7 C17 173.8(2) . . . . no
N5 Ni2 N7 C17 -2.7(2) . . . . no
N8 Ni2 N7 C18 -9.2(2) . . . . no
N5 Ni2 N7 C18 174.3(2) . . . . no
N7 Ni2 N8 C20 -174.8(2) . . . . no
O5 Ni2 N8 C20 3.8(2) . . . . no
N5 Ni2 N8 C20 -155.9(4) . . . . no
N7 Ni2 N8 C19 -1.3(2) . . . . no
O5 Ni2 N8 C19 177.3(2) . . . . no
N5 Ni2 N8 C19 17.5(6) . . . . no
C14 N5 C13 N6 1.2(3) . . . . no
Ni2 N5 C13 N6 -176.84(17) . . . . no
C14 N5 C13 C17 179.6(2) . . . . no
Ni2 N5 C13 C17 1.6(3) . . . . no
C15 N6 C13 N5 -1.0(3) . . . . no
C16 N6 C13 N5 -179.6(2) . . . . no
C15 N6 C13 C17 -179.0(3) . . . . no
C16 N6 C13 C17 2.3(5) . . . . no
C13 N5 C14 C15 -0.9(3) . . . . no
Ni2 N5 C14 C15 176.1(2) . . . . no
N5 C14 C15 N6 0.4(3) . . . . no
C13 N6 C15 C14 0.3(3) . . . . no
C16 N6 C15 C14 179.0(2) . . . . no
C18 N7 C17 O4 8.3(5) . . . . no
Ni2 N7 C17 O4 -174.9(2) . . . . no
C18 N7 C17 C13 -172.9(2) . . . . no
Ni2 N7 C17 C13 3.9(3) . . . . no
N5 C13 C17 O4 175.5(2) . . . . no
N6 C13 C17 O4 -6.6(5) . . . . no
N5 C13 C17 N7 -3.4(3) . . . . no
N6 C13 C17 N7 174.5(3) . . . . no
C17 N7 C18 C19 -166.4(3) . . . . no
Ni2 N7 C18 C19 16.7(3) . . . . no
C20 N8 C19 C18 -175.5(3) . . . . no
Ni2 N8 C19 C18 10.6(3) . . . . no
N7 C18 C19 N8 -16.4(3) . . . . no
C19 N8 C20 C21 -176.3(3) . . . . no
Ni2 N8 C20 C21 -3.0(4) . . . . no
C19 N8 C20 C23 3.1(4) . . . . no
Ni2 N8 C20 C23 176.3(2) . . . . no
N8 C20 C21 C22 0.5(5) . . . . no
C23 C20 C21 C22 -178.9(3) . . . . no
Ni2 O5 C22 O6 -176.78(17) . . . . no
Ni2 O5 C22 C21 1.8(4) . . . . no
C24 O6 C22 O5 -3.5(4) . . . . no
C24 O6 C22 C21 177.8(2) . . . . no
C20 C21 C22 O5 0.1(5) . . . . no
C20 C21 C22 O6 178.7(3) . . . . no

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.12
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.069

#===END



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
