 
data_60
  
_audit_creation_method            'SHELXL-2018/3' 
_shelx_SHELXL_version_number      '2018/3' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety
 'C22 H24 N6 Ni O6' 
_chemical_formula_sum 
 'C22 H24 N6 Ni O6' 
_chemical_formula_weight          527.18 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0181   0.0091 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0311   0.0180 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'Ni'  'Ni'  -3.0029   0.5091 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0492   0.0322 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_space_group_crystal_system       monoclinic 
_space_group_IT_number            14 
_space_group_name_H-M_alt         'P 21/c' 
_space_group_name_Hall            '-P 2ybc' 
  
_shelx_space_group_comment 
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
; 
  
loop_ 
 _space_group_symop_operation_xyz 
 'x, y, z' 
 '-x, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y-1/2, z-1/2' 
  
_cell_length_a                    9.9278(2) 
_cell_length_b                    15.0829(4) 
_cell_length_c                    15.8467(4) 
_cell_angle_alpha                 90 
_cell_angle_beta                  90.7481(19) 
_cell_angle_gamma                 90 
_cell_volume                      2372.68(9) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     173(2) 
_cell_measurement_reflns_used     3117 
_cell_measurement_theta_min       4.0190 
_cell_measurement_theta_max       73.0270 
  
_exptl_crystal_description        'canoe-shaped blocks' 
_exptl_crystal_colour             'Pale blue' 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.476 
_exptl_crystal_F_000              1096 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.222 
_exptl_crystal_size_mid           0.208 
_exptl_crystal_size_min           0.129 
_exptl_absorpt_coefficient_mu     1.621 
_shelx_estimated_absorpt_T_min    ? 
_shelx_estimated_absorpt_T_max    ? 
_exptl_absorpt_correction_type    analytical 
_exptl_absorpt_correction_T_min   0.779 
_exptl_absorpt_correction_T_max   0.856 
_exptl_absorpt_process_details     
; 
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
; 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       173(2) 
_diffrn_radiation_wavelength      1.54184 
_diffrn_radiation_type            CuK\a 
_diffrn_source                    'Enhance Ultra (Cu) X-ray Source' 
_diffrn_measurement_device_type   'Agilent Xcalibur PX Ultra A' 
_diffrn_measurement_method        'omega scans' 
_diffrn_detector_area_resol_mean  10.4115 
_diffrn_reflns_number             7313 
_diffrn_reflns_av_unetI/netI      0.0395 
_diffrn_reflns_av_R_equivalents   0.0268 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        12 
_diffrn_reflns_limit_k_min        -18 
_diffrn_reflns_limit_k_max        13 
_diffrn_reflns_limit_l_min        -19 
_diffrn_reflns_limit_l_max        13 
_diffrn_reflns_theta_min          4.046 
_diffrn_reflns_theta_max          73.849 
_diffrn_reflns_theta_full         67.684 
_diffrn_measured_fraction_theta_max   0.941 
_diffrn_measured_fraction_theta_full  0.981 
_diffrn_reflns_Laue_measured_fraction_max    0.941 
_diffrn_reflns_Laue_measured_fraction_full   0.981 
_diffrn_reflns_point_group_measured_fraction_max   0.941 
_diffrn_reflns_point_group_measured_fraction_full  0.981 
_reflns_number_total              4522 
_reflns_number_gt                 3552 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.000 
_reflns_Friedel_fraction_max      . 
_reflns_Friedel_fraction_full     . 
  
_reflns_special_details 
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
; 
  
_computing_data_collection        'CrysAlisPro, Rigaku OD' 
_computing_cell_refinement        'CrysAlisPro, Rigaku OD' 
_computing_data_reduction         'CrysAlisPro, Rigaku OD' 
_computing_structure_solution     'SHELXS-2014 (Sheldrick, 2017)' 
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'CIFTAB-2014 (Sheldrick, 2017)' 
_refine_special_details           ? 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.0623P)²+0.5453P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    mixed 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        . 
_refine_ls_number_reflns          4522 
_refine_ls_number_parameters      326 
_refine_ls_number_restraints      2 
_refine_ls_R_factor_all           0.0549 
_refine_ls_R_factor_gt            0.0400 
_refine_ls_wR_factor_ref          0.1189 
_refine_ls_wR_factor_gt           0.1020 
_refine_ls_goodness_of_fit_ref    1.038 
_refine_ls_restrained_S_all       1.038 
_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_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 0.46486(3) 0.26098(2) 0.62487(2) 0.02128(13) Uani 1 1 d . . . . . 
N1 N 0.1573(2) 0.25556(18) 0.36255(14) 0.0409(6) Uani 1 1 d . . . . . 
N2 N 0.29100(18) 0.27399(15) 0.38168(11) 0.0302(4) Uani 1 1 d D . . . . 
H2 H 0.3517(4) 0.276(2) 0.3400(2) 0.042(9) Uiso 1 1 d D . . . . 
C3 C 0.3218(2) 0.26248(15) 0.46446(14) 0.0232(4) Uani 1 1 d . . . . . 
O3 O 0.44106(14) 0.27218(11) 0.49543(9) 0.0243(3) Uani 1 1 d . . . . . 
C4 C 0.1998(2) 0.23675(16) 0.50241(15) 0.0277(5) Uani 1 1 d . . . . . 
C5 C 0.1042(2) 0.2352(2) 0.43519(16) 0.0376(6) Uani 1 1 d . . . . . 
H5A H 0.011744 0.220950 0.442097 0.045 Uiso 1 1 calc R U . . . 
C6 C 0.1859(2) 0.20517(16) 0.58598(14) 0.0258(5) Uani 1 1 d . . . . . 
O6 O 0.27643(15) 0.20380(11) 0.64089(10) 0.0265(3) Uani 1 1 d . . . . . 
O7 O 0.06298(16) 0.17326(14) 0.60259(11) 0.0353(4) Uani 1 1 d . . . . . 
C8 C 0.0460(3) 0.1287(2) 0.68254(17) 0.0407(6) Uani 1 1 d . . . . . 
H8A H -0.050330 0.129155 0.697940 0.049 Uiso 1 1 calc R U . . . 
H8B H 0.097495 0.160325 0.727172 0.049 Uiso 1 1 calc R U . . . 
C9 C 0.0952(3) 0.0340(2) 0.6764(2) 0.0546(8) Uani 1 1 d . . . . . 
H9A H 0.089663 0.005606 0.731836 0.082 Uiso 1 1 calc R U . . . 
H9B H 0.188932 0.033704 0.657705 0.082 Uiso 1 1 calc R U . . . 
H9C H 0.038971 0.001504 0.635635 0.082 Uiso 1 1 calc R U . . . 
N11 N 0.76978(19) 0.28149(16) 0.88748(13) 0.0328(5) Uani 1 1 d . . . . . 
N12 N 0.63645(17) 0.26217(13) 0.86843(11) 0.0260(4) Uani 1 1 d D . . . . 
H12 H 0.5797(5) 0.2481(8) 0.9102(3) 0.025(7) Uiso 1 1 d D . . . . 
C13 C 0.6064(2) 0.26861(15) 0.78515(13) 0.0225(4) Uani 1 1 d . . . . . 
O13 O 0.48913(15) 0.25263(11) 0.75401(10) 0.0251(3) Uani 1 1 d . . . . . 
C14 C 0.7276(2) 0.29596(15) 0.74692(14) 0.0250(4) Uani 1 1 d . . . . . 
C15 C 0.8224(2) 0.30195(18) 0.81446(15) 0.0314(5) Uani 1 1 d . . . . . 
H15A H 0.913726 0.318882 0.807584 0.038 Uiso 1 1 calc R U . . . 
C16 C 0.7421(2) 0.32214(15) 0.66175(14) 0.0240(4) Uani 1 1 d . . . . . 
O16 O 0.65178(15) 0.31853(11) 0.60652(10) 0.0256(3) Uani 1 1 d . . . . . 
O17 O 0.86452(16) 0.35358(14) 0.64388(11) 0.0354(4) Uani 1 1 d . . . . . 
C18 C 0.8834(3) 0.3923(2) 0.56115(17) 0.0403(6) Uani 1 1 d . . . . . 
H18A H 0.826070 0.361065 0.519087 0.048 Uiso 1 1 calc R U . . . 
H18B H 0.978531 0.385614 0.544340 0.048 Uiso 1 1 calc R U . . . 
C19 C 0.8463(3) 0.4896(2) 0.5631(2) 0.0541(8) Uani 1 1 d . . . . . 
H19A H 0.907002 0.521002 0.602160 0.081 Uiso 1 1 calc R U . . . 
H19B H 0.753219 0.496104 0.582017 0.081 Uiso 1 1 calc R U . . . 
H19C H 0.854654 0.514798 0.506398 0.081 Uiso 1 1 calc R U . . . 
N21 N 0.37722(19) 0.38580(13) 0.64016(12) 0.0257(4) Uani 1 1 d . . . . . 
C22 C 0.2694(3) 0.39743(18) 0.68918(17) 0.0351(5) Uani 1 1 d . . . . . 
H22A H 0.232215 0.347746 0.717431 0.042 Uiso 1 1 calc R U . . . 
C23 C 0.2109(3) 0.4800(2) 0.6996(2) 0.0450(7) Uani 1 1 d . . . . . 
H23 H 0.133229 0.486161 0.733522 0.054 Uiso 1 1 calc R U . . . 
C24 C 0.2647(3) 0.5524(2) 0.6612(2) 0.0470(7) Uani 1 1 d . . . . . 
H24A H 0.225920 0.609382 0.668802 0.056 Uiso 1 1 calc R U . . . 
C25 C 0.3764(3) 0.54186(19) 0.61117(19) 0.0431(6) Uani 1 1 d . . . . . 
H25A H 0.416151 0.591093 0.583628 0.052 Uiso 1 1 calc R U . . . 
C26 C 0.4287(3) 0.45700(17) 0.60236(16) 0.0336(5) Uani 1 1 d . . . . . 
H26A H 0.505124 0.449243 0.567635 0.040 Uiso 1 1 calc R U . . . 
N31 N 0.5492(2) 0.13486(14) 0.61290(12) 0.0298(4) Uani 1 1 d . . . . . 
C32 C 0.6524(3) 0.1188(2) 0.56147(17) 0.0400(6) Uani 1 1 d . . . . . 
H32A H 0.692391 0.167055 0.532563 0.048 Uiso 1 1 calc R U . . . 
C33 C 0.7029(4) 0.0341(3) 0.5489(2) 0.0639(10) Uani 1 1 d . . . . . 
H33A H 0.775602 0.024535 0.511626 0.077 Uiso 1 1 calc R U . . . 
C34 C 0.6461(5) -0.0355(2) 0.5912(3) 0.0767(13) Uani 1 1 d . . . . . 
H34A H 0.679178 -0.094007 0.583774 0.092 Uiso 1 1 calc R U . . . 
C35 C 0.5409(4) -0.0195(2) 0.6446(3) 0.0622(10) Uani 1 1 d . . . . . 
H35A H 0.499920 -0.066823 0.674341 0.075 Uiso 1 1 calc R U . . . 
C36 C 0.4955(3) 0.06648(19) 0.6543(2) 0.0428(6) Uani 1 1 d . . . . . 
H36A H 0.423371 0.077394 0.691710 0.051 Uiso 1 1 calc R U . . . 
  
  
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
  
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
Ni1 O13 2.0613(16) . ? 
Ni1 O3 2.0686(15) . ? 
Ni1 O16 2.0726(15) . ? 
Ni1 O6 2.0785(15) . ? 
Ni1 N31 2.088(2) . ? 
Ni1 N21 2.0895(19) . ? 
N1 C5 1.309(3) . ? 
N1 N2 1.386(3) . ? 
N2 C3 1.354(3) . ? 
C3 O3 1.284(3) . ? 
C3 C4 1.414(3) . ? 
C4 C6 1.416(3) . ? 
C4 C5 1.418(3) . ? 
C6 O6 1.243(3) . ? 
C6 O7 1.341(3) . ? 
O7 C8 1.446(3) . ? 
C8 C9 1.512(5) . ? 
N11 C15 1.312(3) . ? 
N11 N12 1.385(3) . ? 
N12 C13 1.353(3) . ? 
C13 O13 1.282(3) . ? 
C13 C14 1.415(3) . ? 
C14 C16 1.415(3) . ? 
C14 C15 1.419(3) . ? 
C16 O16 1.246(3) . ? 
C16 O17 1.338(3) . ? 
O17 C18 1.450(3) . ? 
C18 C19 1.514(5) . ? 
N21 C26 1.335(3) . ? 
N21 C22 1.343(3) . ? 
C22 C23 1.385(4) . ? 
C23 C24 1.363(5) . ? 
C24 C25 1.381(4) . ? 
C25 C26 1.389(4) . ? 
N31 C36 1.337(4) . ? 
N31 C32 1.339(3) . ? 
C32 C33 1.387(4) . ? 
C33 C34 1.370(6) . ? 
C34 C35 1.374(6) . ? 
C35 C36 1.382(5) . ? 
  
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 
O13 Ni1 O3 178.81(7) . . ? 
O13 Ni1 O16 94.11(6) . . ? 
O3 Ni1 O16 85.27(6) . . ? 
O13 Ni1 O6 86.97(6) . . ? 
O3 Ni1 O6 93.65(6) . . ? 
O16 Ni1 O6 178.91(6) . . ? 
O13 Ni1 N31 89.58(7) . . ? 
O3 Ni1 N31 91.44(7) . . ? 
O16 Ni1 N31 90.45(7) . . ? 
O6 Ni1 N31 89.76(8) . . ? 
O13 Ni1 N21 89.05(7) . . ? 
O3 Ni1 N21 89.94(7) . . ? 
O16 Ni1 N21 90.79(7) . . ? 
O6 Ni1 N21 89.02(7) . . ? 
N31 Ni1 N21 178.21(8) . . ? 
C5 N1 N2 104.50(19) . . ? 
C3 N2 N1 112.94(18) . . ? 
O3 C3 N2 123.45(19) . . ? 
O3 C3 C4 131.3(2) . . ? 
N2 C3 C4 105.26(19) . . ? 
C3 O3 Ni1 117.55(13) . . ? 
C3 C4 C6 125.8(2) . . ? 
C3 C4 C5 104.7(2) . . ? 
C6 C4 C5 128.7(2) . . ? 
N1 C5 C4 112.5(2) . . ? 
O6 C6 O7 120.5(2) . . ? 
O6 C6 C4 125.6(2) . . ? 
O7 C6 C4 113.82(19) . . ? 
C6 O6 Ni1 123.45(14) . . ? 
C6 O7 C8 117.10(19) . . ? 
O7 C8 C9 109.9(2) . . ? 
C15 N11 N12 104.32(18) . . ? 
C13 N12 N11 113.28(17) . . ? 
O13 C13 N12 123.34(19) . . ? 
O13 C13 C14 131.5(2) . . ? 
N12 C13 C14 105.13(18) . . ? 
C13 O13 Ni1 117.68(13) . . ? 
C13 C14 C16 126.0(2) . . ? 
C13 C14 C15 104.75(19) . . ? 
C16 C14 C15 128.8(2) . . ? 
N11 C15 C14 112.5(2) . . ? 
O16 C16 O17 120.9(2) . . ? 
O16 C16 C14 125.19(19) . . ? 
O17 C16 C14 113.88(19) . . ? 
C16 O16 Ni1 123.86(14) . . ? 
C16 O17 C18 117.55(18) . . ? 
O17 C18 C19 109.7(2) . . ? 
C26 N21 C22 117.9(2) . . ? 
C26 N21 Ni1 120.69(16) . . ? 
C22 N21 Ni1 121.42(17) . . ? 
N21 C22 C23 121.7(2) . . ? 
C24 C23 C22 120.0(3) . . ? 
C23 C24 C25 119.1(3) . . ? 
C24 C25 C26 117.9(3) . . ? 
N21 C26 C25 123.4(2) . . ? 
C36 N31 C32 118.2(2) . . ? 
C36 N31 Ni1 119.67(19) . . ? 
C32 N31 Ni1 122.08(18) . . ? 
N31 C32 C33 122.3(3) . . ? 
C34 C33 C32 118.9(3) . . ? 
C33 C34 C35 119.2(3) . . ? 
C34 C35 C36 119.0(3) . . ? 
N31 C36 C35 122.4(3) . . ? 
  
loop_ 
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
 _geom_hbond_publ_flag 
N2 H2 O13  0.9000(1) 1.991(8) 2.868(2) 165(3) 4_565 yes 
N12 H12 O3  0.9000(1) 1.965(2) 2.861(2) 173.1(9) 4_566 yes 
  
_refine_diff_density_max    0.710 
_refine_diff_density_min   -0.360 
_refine_diff_density_rms    0.067 
  
  
  
#===END

