# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2016

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

data_Ni(DQPD)
_database_code_depnum_ccdc_archive 'CCDC 1401801'
_audit_update_record             
;
2015-05-19 deposited with the CCDC.
2016-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H15 N5 Ni O2, H2 O'
_chemical_formula_sum            'C25 H17 N5 Ni O3'
_chemical_formula_weight         494.13

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'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
_space_group_IT_number           14
_symmetry_space_group_name_H-M   P21/c
_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                   11.5545(5)
_cell_length_b                   19.8056(9)
_cell_length_c                   9.1539(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.097(3)
_cell_angle_gamma                90.00
_cell_volume                     2089.46(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       blocks
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016
_exptl_absorpt_coefficient_mu    0.969
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.720
_exptl_absorpt_correction_T_max  0.735
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            35617
_diffrn_reflns_av_R_equivalents  0.0965
_diffrn_reflns_av_sigmaI/netI    0.0805
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         28.48
_reflns_number_total             5295
_reflns_number_gt                2778
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_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)+(0.1000P)²+0.0000P] 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         5295
_refine_ls_number_parameters     315
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1267
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1753
_refine_ls_wR_factor_gt          0.1413
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_restrained_S_all      0.933
_refine_ls_shift/su_max          0.002
_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 0.13174(4) 0.03153(2) 0.64275(6) 0.0386(2) Uani 1 1 d . . .
N2 N 0.1993(3) -0.03388(15) 0.5377(4) 0.0388(8) Uani 1 1 d . . .
N1 N 0.2533(3) 0.08615(15) 0.5740(4) 0.0393(8) Uani 1 1 d . . .
N3 N 0.0329(3) -0.03814(15) 0.6870(4) 0.0417(8) Uani 1 1 d . . .
O1 O 0.4093(3) 0.07839(14) 0.4276(3) 0.0525(8) Uani 1 1 d . . .
O2 O 0.0064(3) -0.15493(14) 0.6623(3) 0.0593(9) Uani 1 1 d . . .
C1 C 0.3247(4) 0.0542(2) 0.4845(5) 0.0413(10) Uani 1 1 d . . .
C6 C 0.1565(3) -0.0972(2) 0.5416(5) 0.0424(10) Uani 1 1 d . . .
C2 C 0.2917(4) -0.01816(19) 0.4636(4) 0.0411(10) Uani 1 1 d . . .
C3 C 0.3436(4) -0.0673(2) 0.3851(5) 0.0493(11) Uani 1 1 d . . .
H3 H 0.4061 -0.0568 0.3308 0.059 Uiso 1 1 calc R . .
C7 C 0.0560(4) -0.1016(2) 0.6360(5) 0.0455(10) Uani 1 1 d . . .
C5 C 0.2071(4) -0.1482(2) 0.4662(5) 0.0535(12) Uani 1 1 d . . .
H5 H 0.1783 -0.1920 0.4679 0.064 Uiso 1 1 calc R . .
C4 C 0.3014(4) -0.1329(2) 0.3881(5) 0.0556(12) Uani 1 1 d . . .
H4 H 0.3370 -0.1668 0.3370 0.067 Uiso 1 1 calc R . .
C8 C -0.0527(3) -0.02180(19) 0.7825(4) 0.0383(9) Uani 1 1 d . . .
C10 C -0.2141(4) -0.0338(2) 0.9316(5) 0.0531(12) Uani 1 1 d . . .
H10 H -0.2713 -0.0611 0.9672 0.064 Uiso 1 1 calc R . .
C13 C -0.0460(3) 0.0477(2) 0.8230(4) 0.0386(9) Uani 1 1 d . . .
C11 C -0.2075(4) 0.0316(2) 0.9741(5) 0.0506(11) Uani 1 1 d . . .
H11 H -0.2584 0.0482 1.0396 0.061 Uiso 1 1 calc R . .
C12 C -0.1233(4) 0.0748(2) 0.9191(5) 0.0426(10) Uani 1 1 d . . .
C14 C 0.0443(4) 0.1506(2) 0.7955(5) 0.0458(10) Uani 1 1 d . . .
H14 H 0.1002 0.1769 0.7545 0.055 Uiso 1 1 calc R . .
C15 C -0.0296(4) 0.1814(2) 0.8890(5) 0.0533(11) Uani 1 1 d . . .
H15 H -0.0233 0.2274 0.9080 0.064 Uiso 1 1 calc R . .
C16 C -0.1115(4) 0.1439(2) 0.9527(5) 0.0526(11) Uani 1 1 d . . .
H16 H -0.1592 0.1639 1.0179 0.063 Uiso 1 1 calc R . .
C9 C -0.1376(4) -0.0620(2) 0.8357(5) 0.0481(11) Uani 1 1 d . . .
H9 H -0.1441 -0.1071 0.8085 0.058 Uiso 1 1 calc R . .
C17 C 0.2845(3) 0.15383(19) 0.6119(4) 0.0384(9) Uani 1 1 d . . .
C22 C 0.3701(3) 0.1675(2) 0.7273(4) 0.0405(9) Uani 1 1 d . . .
C21 C 0.3982(4) 0.2359(2) 0.7625(5) 0.0455(10) Uani 1 1 d . . .
C20 C 0.3369(4) 0.2882(2) 0.6867(5) 0.0514(11) Uani 1 1 d . . .
H20 H 0.3529 0.3329 0.7120 0.062 Uiso 1 1 calc R . .
C19 C 0.2554(4) 0.2743(2) 0.5780(5) 0.0517(11) Uani 1 1 d . . .
H19 H 0.2165 0.3093 0.5280 0.062 Uiso 1 1 calc R . .
C18 C 0.2287(4) 0.2063(2) 0.5395(5) 0.0461(10) Uani 1 1 d . . .
H18 H 0.1725 0.1974 0.4641 0.055 Uiso 1 1 calc R . .
N5 N 0.4211(3) 0.11406(18) 0.8021(4) 0.0501(9) Uani 1 1 d . . .
C25 C 0.4850(4) 0.2483(3) 0.8735(5) 0.0607(13) Uani 1 1 d . . .
H25 H 0.5066 0.2923 0.8983 0.073 Uiso 1 1 calc R . .
N4 N 0.0386(3) 0.08545(16) 0.7623(4) 0.0397(8) Uani 1 1 d . . .
C23 C 0.5010(4) 0.1289(3) 0.9078(5) 0.0659(14) Uani 1 1 d . . .
H23 H 0.5355 0.0934 0.9613 0.079 Uiso 1 1 calc R . .
C24 C 0.5372(4) 0.1949(3) 0.9448(6) 0.0713(15) Uani 1 1 d . . .
H24 H 0.5964 0.2021 1.0175 0.086 Uiso 1 1 calc R . .
O3 O 0.5737(4) 0.0384(2) 0.2170(4) 0.0772(11) Uani 1 1 d D . .
H3OB H 0.553(8) -0.006(2) 0.180(10) 0.21(4) Uiso 1 1 d D . .
H3OA H 0.514(5) 0.048(3) 0.281(7) 0.15(3) Uiso 1 1 d 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 N2 1.822(3) . ?
Ni1 N3 1.855(3) . ?
Ni1 N4 1.914(3) . ?
Ni1 N1 1.915(3) . ?
N2 C2 1.341(5) . ?
N2 C6 1.349(5) . ?
N1 C1 1.359(5) . ?
N1 C17 1.425(5) . ?
N3 C7 1.374(5) . ?
N3 C8 1.403(5) . ?
O1 C1 1.237(5) . ?
O2 C7 1.234(5) . ?
C1 C2 1.492(5) . ?
C6 C5 1.377(5) . ?
C6 C7 1.499(6) . ?
C2 C3 1.372(6) . ?
C3 C4 1.389(6) . ?
C5 C4 1.378(6) . ?
C8 C9 1.379(5) . ?
C8 C13 1.426(5) . ?
C10 C11 1.353(5) . ?
C10 C9 1.405(6) . ?
C13 N4 1.379(5) . ?
C13 C12 1.404(5) . ?
C11 C12 1.415(6) . ?
C12 C16 1.408(6) . ?
C14 N4 1.326(5) . ?
C14 C15 1.393(5) . ?
C15 C16 1.366(6) . ?
C17 C18 1.370(5) . ?
C17 C22 1.421(5) . ?
C22 N5 1.370(5) . ?
C22 C21 1.425(5) . ?
C21 C25 1.397(6) . ?
C21 C20 1.409(6) . ?
C20 C19 1.349(6) . ?
C19 C18 1.419(5) . ?
N5 C23 1.322(6) . ?
C25 C24 1.361(7) . ?
C23 C24 1.407(7) . ?

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 N3 83.13(14) . . ?
N2 Ni1 N4 167.95(14) . . ?
N3 Ni1 N4 84.83(14) . . ?
N2 Ni1 N1 82.87(14) . . ?
N3 Ni1 N1 165.94(14) . . ?
N4 Ni1 N1 109.17(14) . . ?
C2 N2 C6 122.4(3) . . ?
C2 N2 Ni1 119.2(3) . . ?
C6 N2 Ni1 118.4(3) . . ?
C1 N1 C17 115.6(3) . . ?
C1 N1 Ni1 115.2(3) . . ?
C17 N1 Ni1 129.1(2) . . ?
C7 N3 C8 125.8(3) . . ?
C7 N3 Ni1 117.9(3) . . ?
C8 N3 Ni1 115.9(2) . . ?
O1 C1 N1 127.2(4) . . ?
O1 C1 C2 121.4(4) . . ?
N1 C1 C2 111.4(3) . . ?
N2 C6 C5 119.9(4) . . ?
N2 C6 C7 111.7(3) . . ?
C5 C6 C7 128.3(4) . . ?
N2 C2 C3 119.6(4) . . ?
N2 C2 C1 111.3(3) . . ?
C3 C2 C1 129.1(4) . . ?
C2 C3 C4 119.1(4) . . ?
O2 C7 N3 127.7(4) . . ?
O2 C7 C6 123.6(4) . . ?
N3 C7 C6 108.7(3) . . ?
C4 C5 C6 118.6(4) . . ?
C5 C4 C3 120.5(4) . . ?
C9 C8 N3 129.6(4) . . ?
C9 C8 C13 119.5(4) . . ?
N3 C8 C13 110.9(3) . . ?
C11 C10 C9 122.3(4) . . ?
N4 C13 C12 123.1(4) . . ?
N4 C13 C8 116.5(3) . . ?
C12 C13 C8 120.5(4) . . ?
C10 C11 C12 120.2(4) . . ?
C13 C12 C16 116.9(4) . . ?
C13 C12 C11 118.4(4) . . ?
C16 C12 C11 124.7(4) . . ?
N4 C14 C15 123.0(4) . . ?
C16 C15 C14 119.8(4) . . ?
C15 C16 C12 119.7(4) . . ?
C8 C9 C10 119.1(4) . . ?
C18 C17 C22 119.6(4) . . ?
C18 C17 N1 119.6(4) . . ?
C22 C17 N1 120.7(3) . . ?
N5 C22 C17 118.4(4) . . ?
N5 C22 C21 122.6(4) . . ?
C17 C22 C21 119.0(4) . . ?
C25 C21 C20 122.6(4) . . ?
C25 C21 C22 118.1(4) . . ?
C20 C21 C22 119.3(4) . . ?
C19 C20 C21 120.8(4) . . ?
C20 C19 C18 120.4(4) . . ?
C17 C18 C19 120.8(4) . . ?
C23 N5 C22 116.5(4) . . ?
C24 C25 C21 118.9(5) . . ?
C14 N4 C13 117.4(3) . . ?
C14 N4 Ni1 130.8(3) . . ?
C13 N4 Ni1 111.8(3) . . ?
N5 C23 C24 124.3(5) . . ?
C25 C24 C23 119.5(5) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        28.48
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.774
_refine_diff_density_min         -0.766
_refine_diff_density_rms         0.072
