# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2024

####################################################################### 
# 
# 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_21gtu243_ds_35_0m
_database_code_depnum_ccdc_archive 'CCDC 2312403'
loop_
_audit_author_name
_audit_author_address
'Yunus Zorlu'
;Gebze Technical University
Turkey
;
_audit_update_record             
;
2023-12-06 deposited with the CCDC.	2024-05-09 downloaded from the CCDC.
;
_audit_creation_date             2021-08-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 N2 O2'
_chemical_formula_sum            'C20 H16 N2 O2'
_chemical_formula_weight         316.35
_chemical_melting_point          ?
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'

_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.
;
_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                   5.9603(13)
_cell_length_b                   16.543(3)
_cell_length_c                   16.323(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.415(5)
_cell_angle_gamma                90
_cell_volume                     1609.0(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1827
_cell_measurement_temperature    298
_cell_measurement_theta_max      20.79
_cell_measurement_theta_min      2.46
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0662 before and 0.0490 after correction.
The Ratio of minimum to maximum transmission is 0.9271.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 -2.00 0.0220
0.00 1.00 2.00 0.0460
1.00 -3.00 2.00 0.0320
0.00 -1.00 -3.00 0.0200
0.00 1.00 -3.00 0.0210
0.00 -1.00 3.00 0.0440
0.00 1.00 -1.00 0.0270
1.00 -3.00 -2.00 0.0300
1.00 0.00 -3.00 0.0370
0.00 -3.00 1.00 0.0270
1.00 2.00 -2.00 0.0460
0.00 -3.00 -1.00 0.0320
1.00 3.00 1.00 0.0580
-3.00 1.00 0.00 0.0850
3.00 0.00 2.00 0.0410

_exptl_crystal_size_max          0.176
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.072
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15325
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.088
_diffrn_reflns_theta_max         25.088
_diffrn_reflns_theta_min         1.753
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  
'Bruker APEX II QUAZAR three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1641
_reflns_number_total             2850
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2850
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1031
_refine_ls_R_factor_gt           0.0470
_refine_ls_restrained_S_all      1.029
_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)+(0.0337P)²+0.6200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.1162
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
  C14(H14), C17(H17), C18(H18), C19(H19), C20(H20)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O1 O 0.1588(3) 0.38429(11) 0.48182(11) 0.0656(5) Uani 1 1 d . . . . .
H1 H 0.2610 0.3515 0.4776 0.098 Uiso 1 1 calc R U . . .
O2 O 0.2949(3) 0.35227(12) 0.27537(12) 0.0658(5) Uani 1 1 d . . . . .
H2 H 0.3540 0.3195 0.3068 0.099 Uiso 1 1 calc R U . . .
N1 N 0.3893(3) 0.25695(11) 0.51375(12) 0.0477(5) Uani 1 1 d . . . . .
N2 N 0.6043(3) 0.29312(12) 0.37488(11) 0.0451(5) Uani 1 1 d . . . . .
C1 C 0.4417(4) 0.41214(15) 0.25960(14) 0.0469(6) Uani 1 1 d . . . . .
C2 C 0.3776(5) 0.47207(17) 0.20458(15) 0.0596(8) Uani 1 1 d . . . . .
H2A H 0.2366 0.4705 0.1789 0.071 Uiso 1 1 calc R U . . .
C3 C 0.5234(6) 0.53376(18) 0.18821(17) 0.0702(9) Uani 1 1 d . . . . .
H3 H 0.4814 0.5735 0.1506 0.084 Uiso 1 1 calc R U . . .
C4 C 0.7304(6) 0.53758(18) 0.22658(18) 0.0713(9) Uani 1 1 d . . . . .
H4 H 0.8263 0.5805 0.2161 0.086 Uiso 1 1 calc R U . . .
C5 C 0.7958(4) 0.47789(17) 0.28040(16) 0.0588(7) Uani 1 1 d . . . . .
H5 H 0.9370 0.4805 0.3058 0.071 Uiso 1 1 calc R U . . .
C6 C 0.6548(4) 0.41374(15) 0.29748(14) 0.0431(6) Uani 1 1 d . . . . .
C7 C 0.7312(4) 0.35067(15) 0.35310(13) 0.0469(6) Uani 1 1 d . . . . .
H7 H 0.8781 0.3523 0.3736 0.056 Uiso 1 1 calc R U . . .
C8 C 0.6928(4) 0.23051(14) 0.42558(14) 0.0434(6) Uani 1 1 d . . . . .
C9 C 0.8852(4) 0.18920(15) 0.40523(15) 0.0523(7) Uani 1 1 d . . . . .
H9 H 0.9645 0.2049 0.3595 0.063 Uiso 1 1 calc R U . . .
C10 C 0.9602(5) 0.12513(15) 0.45210(16) 0.0583(7) Uani 1 1 d . . . . .
H10 H 1.0910 0.0980 0.4387 0.070 Uiso 1 1 calc R U . . .
C11 C 0.8409(5) 0.10148(16) 0.51882(17) 0.0648(8) Uani 1 1 d . . . . .
H11 H 0.8884 0.0571 0.5497 0.078 Uiso 1 1 calc R U . . .
C12 C 0.6524(5) 0.14280(15) 0.54017(16) 0.0604(7) Uani 1 1 d . . . . .
H12 H 0.5746 0.1266 0.5861 0.072 Uiso 1 1 calc R U . . .
C13 C 0.5752(4) 0.20816(14) 0.49483(15) 0.0450(6) Uani 1 1 d . . . . .
C14 C 0.2691(4) 0.24478(15) 0.57608(15) 0.0515(7) Uani 1 1 d . . . . .
H14 H 0.3031 0.2016 0.6107 0.062 Uiso 1 1 calc R U . . .
C15 C 0.0823(4) 0.29626(15) 0.59414(14) 0.0474(6) Uani 1 1 d . . . . .
C16 C 0.0308(4) 0.36377(15) 0.54541(15) 0.0508(6) Uani 1 1 d . . . . .
C17 C -0.1549(5) 0.41058(16) 0.56135(17) 0.0611(7) Uani 1 1 d . . . . .
H17 H -0.1888 0.4552 0.5287 0.073 Uiso 1 1 calc R U . . .
C18 C -0.2895(5) 0.39110(18) 0.62545(17) 0.0645(8) Uani 1 1 d . . . . .
H18 H -0.4150 0.4226 0.6356 0.077 Uiso 1 1 calc R U . . .
C19 C -0.2415(5) 0.32557(19) 0.67494(17) 0.0679(8) Uani 1 1 d . . . . .
H19 H -0.3327 0.3132 0.7186 0.082 Uiso 1 1 calc R U . . .
C20 C -0.0579(4) 0.27894(17) 0.65902(16) 0.0617(8) Uani 1 1 d . . . . .
H20 H -0.0258 0.2346 0.6923 0.074 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
O1 H1 0.8200 . ?
O1 C16 1.347(3) . ?
O2 H2 0.8200 . ?
O2 C1 1.351(3) . ?
N1 C13 1.411(3) . ?
N1 C14 1.275(3) . ?
N2 C7 1.272(3) . ?
N2 C8 1.419(3) . ?
C1 C2 1.385(3) . ?
C1 C6 1.399(3) . ?
C2 H2A 0.9300 . ?
C2 C3 1.371(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.371(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.372(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(3) . ?
C6 C7 1.449(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.383(3) . ?
C8 C13 1.395(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.375(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.373(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.368(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.383(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.438(3) . ?
C15 C16 1.401(3) . ?
C15 C20 1.395(3) . ?
C16 C17 1.381(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.373(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.378(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.369(3) . ?
C20 H20 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 O1 H1 109.5 . . ?
C1 O2 H2 109.5 . . ?
C14 N1 C13 122.9(2) . . ?
C7 N2 C8 119.6(2) . . ?
O2 C1 C2 118.6(2) . . ?
O2 C1 C6 121.0(2) . . ?
C2 C1 C6 120.4(2) . . ?
C1 C2 H2A 120.2 . . ?
C3 C2 C1 119.5(3) . . ?
C3 C2 H2A 120.2 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.9(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.1(3) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C7 122.1(2) . . ?
C5 C6 C1 118.3(2) . . ?
C5 C6 C7 119.6(2) . . ?
N2 C7 C6 122.3(2) . . ?
N2 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C9 C8 N2 121.3(2) . . ?
C9 C8 C13 120.0(2) . . ?
C13 C8 N2 118.6(2) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.5(2) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.6(2) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.4 . . ?
C11 C12 C13 121.3(2) . . ?
C13 C12 H12 119.4 . . ?
C8 C13 N1 116.0(2) . . ?
C12 C13 N1 125.7(2) . . ?
C12 C13 C8 118.3(2) . . ?
N1 C14 H14 119.2 . . ?
N1 C14 C15 121.5(2) . . ?
C15 C14 H14 119.2 . . ?
C16 C15 C14 121.0(2) . . ?
C20 C15 C14 121.0(2) . . ?
C20 C15 C16 117.9(2) . . ?
O1 C16 C15 121.2(2) . . ?
O1 C16 C17 118.4(2) . . ?
C17 C16 C15 120.4(2) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.9(3) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 119.5 . . ?
C17 C18 C19 121.0(3) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 H19 120.4 . . ?
C20 C19 C18 119.2(3) . . ?
C20 C19 H19 120.4 . . ?
C15 C20 H20 119.2 . . ?
C19 C20 C15 121.7(3) . . ?
C19 C20 H20 119.2 . . ?

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
O1 C16 C17 C18 179.7(2) . . . . ?
O2 C1 C2 C3 179.5(2) . . . . ?
O2 C1 C6 C5 -178.4(2) . . . . ?
O2 C1 C6 C7 1.9(3) . . . . ?
N1 C14 C15 C16 -2.5(4) . . . . ?
N1 C14 C15 C20 175.3(2) . . . . ?
N2 C8 C9 C10 -175.6(2) . . . . ?
N2 C8 C13 N1 -7.2(3) . . . . ?
N2 C8 C13 C12 174.8(2) . . . . ?
C1 C2 C3 C4 -1.1(4) . . . . ?
C1 C6 C7 N2 -4.7(3) . . . . ?
C2 C1 C6 C5 2.0(3) . . . . ?
C2 C1 C6 C7 -177.7(2) . . . . ?
C2 C3 C4 C5 1.8(4) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C4 C5 C6 C1 -1.2(4) . . . . ?
C4 C5 C6 C7 178.5(2) . . . . ?
C5 C6 C7 N2 175.6(2) . . . . ?
C6 C1 C2 C3 -0.9(4) . . . . ?
C7 N2 C8 C9 -52.1(3) . . . . ?
C7 N2 C8 C13 131.2(2) . . . . ?
C8 N2 C7 C6 176.2(2) . . . . ?
C8 C9 C10 C11 1.0(4) . . . . ?
C9 C8 C13 N1 176.1(2) . . . . ?
C9 C8 C13 C12 -2.0(4) . . . . ?
C9 C10 C11 C12 -2.0(4) . . . . ?
C10 C11 C12 C13 1.1(4) . . . . ?
C11 C12 C13 N1 -176.9(2) . . . . ?
C11 C12 C13 C8 0.9(4) . . . . ?
C13 N1 C14 C15 179.3(2) . . . . ?
C13 C8 C9 C10 1.1(4) . . . . ?
C14 N1 C13 C8 -178.5(2) . . . . ?
C14 N1 C13 C12 -0.7(4) . . . . ?
C14 C15 C16 O1 -2.3(4) . . . . ?
C14 C15 C16 C17 177.1(2) . . . . ?
C14 C15 C20 C19 -177.4(2) . . . . ?
C15 C16 C17 C18 0.2(4) . . . . ?
C16 C15 C20 C19 0.5(4) . . . . ?
C16 C17 C18 C19 0.5(4) . . . . ?
C17 C18 C19 C20 -0.7(4) . . . . ?
C18 C19 C20 C15 0.2(4) . . . . ?
C20 C15 C16 O1 179.9(2) . . . . ?
C20 C15 C16 C17 -0.7(4) . . . . ?

_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_22gtu440_hd_11_0m
_database_code_depnum_ccdc_archive 'CCDC 2312404'
loop_
_audit_author_name
_audit_author_address
'Yunus Zorlu'
;Gebze Technical University
Turkey
;
_audit_update_record             
;
2023-12-06 deposited with the CCDC.	2024-05-09 downloaded from the CCDC.
;
_audit_creation_date             2023-02-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 N2 Ni O2'
_chemical_formula_sum            'C20 H14 N2 Ni O2'
_chemical_formula_weight         373.04
_chemical_absolute_configuration unk
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.4386(12)
_cell_length_b                   16.592(4)
_cell_length_c                   17.270(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1558.4(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1191
_cell_measurement_temperature    298
_cell_measurement_theta_max      18.26
_cell_measurement_theta_min      2.36
_shelx_estimated_absorpt_T_max   0.901
_shelx_estimated_absorpt_T_min   0.585
_exptl_absorpt_coefficient_mu    1.261
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6200
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1178 before and 0.0592 after correction.
The Ratio of minimum to maximum transmission is 0.8315.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.476
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.084
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_av_unetI/netI     0.0846
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9099
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.702
_diffrn_ambient_temperature      298
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 microsource'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1962
_reflns_number_total             2763
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 
;
 Flack x determined using 616 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2763
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      0.950
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0286P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0776
_refine_ls_wR_factor_ref         0.0868
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C16(H16), C17(H17), C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.35017(14) 0.72281(4) 0.68985(4) 0.0392(2) Uani 1 1 d . . . . .
O1 O 0.3502(8) 0.6263(2) 0.6388(2) 0.0506(11) Uani 1 1 d . . . . .
O2 O 0.0745(7) 0.6825(2) 0.7373(2) 0.0442(11) Uani 1 1 d . . . . .
N1 N 0.6273(9) 0.7622(3) 0.6407(2) 0.0381(12) Uani 1 1 d . . . . .
N2 N 0.3487(10) 0.8189(3) 0.7439(2) 0.0394(12) Uani 1 1 d . . . . .
C1 C -0.0461(11) 0.7129(4) 0.7967(3) 0.0409(15) Uani 1 1 d . . . . .
C2 C -0.2469(12) 0.6694(4) 0.8258(4) 0.0517(19) Uani 1 1 d . . . . .
H2 H -0.291527 0.620732 0.803104 0.062 Uiso 1 1 calc R U . . .
C3 C -0.3786(14) 0.6987(4) 0.8882(4) 0.059(2) Uani 1 1 d . . . . .
H3 H -0.511950 0.669491 0.906845 0.071 Uiso 1 1 calc R U . . .
C4 C -0.3158(14) 0.7709(4) 0.9237(4) 0.0589(18) Uani 1 1 d . . . . .
H4 H -0.403750 0.789178 0.966354 0.071 Uiso 1 1 calc R U . . .
C5 C -0.1251(14) 0.8143(4) 0.8955(3) 0.0544(19) Uani 1 1 d . . . . .
H5 H -0.085307 0.863224 0.918560 0.065 Uiso 1 1 calc R U . . .
C6 C 0.0160(11) 0.7867(4) 0.8312(3) 0.0411(15) Uani 1 1 d . . . . .
C7 C 0.2057(12) 0.8355(4) 0.8027(4) 0.0465(16) Uani 1 1 d . . . . .
H7 H 0.232403 0.884283 0.827935 0.056 Uiso 1 1 calc R U . . .
C8 C 0.5332(12) 0.8732(4) 0.7194(3) 0.0392(16) Uani 1 1 d . . . . .
C9 C 0.5680(13) 0.9513(4) 0.7460(4) 0.052(2) Uani 1 1 d . . . . .
H9 H 0.459552 0.973298 0.781882 0.063 Uiso 1 1 calc R U . . .
C10 C 0.7618(14) 0.9959(4) 0.7194(4) 0.059(2) Uani 1 1 d . . . . .
H10 H 0.788383 1.047647 0.738375 0.070 Uiso 1 1 calc R U . . .
C11 C 0.9185(13) 0.9641(4) 0.6640(4) 0.057(2) Uani 1 1 d . . . . .
H11 H 1.049834 0.994666 0.646002 0.068 Uiso 1 1 calc R U . . .
C12 C 0.8816(12) 0.8874(4) 0.6355(3) 0.0472(17) Uani 1 1 d . . . . .
H12 H 0.985783 0.866797 0.597638 0.057 Uiso 1 1 calc R U . . .
C13 C 0.6911(12) 0.8418(3) 0.6630(3) 0.0353(15) Uani 1 1 d . . . . .
C14 C 0.7669(11) 0.7217(4) 0.5928(3) 0.0437(15) Uani 1 1 d . . . . .
H14 H 0.906639 0.747436 0.574038 0.052 Uiso 1 1 calc R U . . .
C15 C 0.7234(11) 0.6423(4) 0.5672(3) 0.0398(16) Uani 1 1 d . . . . .
C16 C 0.8957(13) 0.6060(4) 0.5168(3) 0.0521(19) Uani 1 1 d . . . . .
H16 H 1.033450 0.635064 0.501430 0.063 Uiso 1 1 calc R U . . .
C17 C 0.8649(14) 0.5298(4) 0.4905(4) 0.0587(19) Uani 1 1 d . . . . .
H17 H 0.979453 0.506978 0.457015 0.070 Uiso 1 1 calc R U . . .
C18 C 0.6604(14) 0.4862(4) 0.5140(3) 0.0521(17) Uani 1 1 d . . . . .
H18 H 0.639465 0.433770 0.496201 0.063 Uiso 1 1 calc R U . . .
C19 C 0.4888(12) 0.5188(4) 0.5628(3) 0.0495(17) Uani 1 1 d . . . . .
H19 H 0.353070 0.488298 0.577333 0.059 Uiso 1 1 calc R U . . .
C20 C 0.5146(12) 0.5976(4) 0.5911(3) 0.0427(16) Uani 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 O1 1.829(4) . ?
Ni1 O2 1.835(4) . ?
Ni1 N1 1.849(5) . ?
Ni1 N2 1.847(5) . ?
O1 C20 1.306(7) . ?
O2 C1 1.318(6) . ?
N1 C13 1.418(7) . ?
N1 C14 1.309(7) . ?
N2 C7 1.308(7) . ?
N2 C8 1.414(7) . ?
C1 C2 1.403(8) . ?
C1 C6 1.402(8) . ?
C2 H2 0.9300 . ?
C2 C3 1.383(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(9) . ?
C4 H4 0.9300 . ?
C4 C5 1.353(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.425(8) . ?
C6 C7 1.401(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.389(8) . ?
C8 C13 1.399(8) . ?
C9 H9 0.9300 . ?
C9 C10 1.368(9) . ?
C10 H10 0.9300 . ?
C10 C11 1.385(9) . ?
C11 H11 0.9300 . ?
C11 C12 1.379(8) . ?
C12 H12 0.9300 . ?
C12 C13 1.369(8) . ?
C14 H14 0.9300 . ?
C14 C15 1.409(8) . ?
C15 C16 1.414(8) . ?
C15 C20 1.418(8) . ?
C16 H16 0.9300 . ?
C16 C17 1.354(8) . ?
C17 H17 0.9300 . ?
C17 C18 1.387(9) . ?
C18 H18 0.9300 . ?
C18 C19 1.369(8) . ?
C19 H19 0.9300 . ?
C19 C20 1.402(8) . ?

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
O1 Ni1 O2 84.04(19) . . ?
O1 Ni1 N1 95.06(19) . . ?
O1 Ni1 N2 178.4(2) . . ?
O2 Ni1 N1 179.0(2) . . ?
O2 Ni1 N2 94.9(2) . . ?
N2 Ni1 N1 86.0(2) . . ?
C20 O1 Ni1 128.6(4) . . ?
C1 O2 Ni1 127.9(4) . . ?
C13 N1 Ni1 113.8(4) . . ?
C14 N1 Ni1 125.5(4) . . ?
C14 N1 C13 120.5(5) . . ?
C7 N2 Ni1 125.3(4) . . ?
C7 N2 C8 121.3(5) . . ?
C8 N2 Ni1 113.3(4) . . ?
O2 C1 C2 118.0(6) . . ?
O2 C1 C6 123.0(5) . . ?
C6 C1 C2 119.0(6) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.1(7) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.3(7) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.3(7) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.4(7) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 118.8(6) . . ?
C7 C6 C1 122.2(6) . . ?
C7 C6 C5 118.9(6) . . ?
N2 C7 C6 126.0(6) . . ?
N2 C7 H7 117.0 . . ?
C6 C7 H7 117.0 . . ?
C9 C8 N2 126.3(6) . . ?
C9 C8 C13 119.6(6) . . ?
C13 C8 N2 114.0(5) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 119.9(6) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.0(6) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.6(7) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.7(6) . . ?
C13 C12 H12 120.1 . . ?
C8 C13 N1 112.7(5) . . ?
C12 C13 N1 127.3(6) . . ?
C12 C13 C8 120.0(5) . . ?
N1 C14 H14 117.2 . . ?
N1 C14 C15 125.5(6) . . ?
C15 C14 H14 117.2 . . ?
C14 C15 C16 118.7(6) . . ?
C14 C15 C20 122.2(6) . . ?
C16 C15 C20 119.1(6) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 C15 121.6(7) . . ?
C17 C16 H16 119.2 . . ?
C16 C17 H17 120.4 . . ?
C16 C17 C18 119.2(6) . . ?
C18 C17 H17 120.4 . . ?
C17 C18 H18 119.3 . . ?
C19 C18 C17 121.4(6) . . ?
C19 C18 H18 119.3 . . ?
C18 C19 H19 119.5 . . ?
C18 C19 C20 121.0(7) . . ?
C20 C19 H19 119.5 . . ?
O1 C20 C15 122.8(6) . . ?
O1 C20 C19 119.4(6) . . ?
C19 C20 C15 117.8(6) . . ?

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 O1 C20 C15 -4.0(8) . . . . ?
Ni1 O1 C20 C19 174.9(4) . . . . ?
Ni1 O2 C1 C2 -177.0(4) . . . . ?
Ni1 O2 C1 C6 3.6(8) . . . . ?
Ni1 N1 C13 C8 1.5(6) . . . . ?
Ni1 N1 C13 C12 -178.3(5) . . . . ?
Ni1 N1 C14 C15 3.5(8) . . . . ?
Ni1 N2 C7 C6 -5.5(8) . . . . ?
Ni1 N2 C8 C9 176.0(5) . . . . ?
Ni1 N2 C8 C13 -4.2(6) . . . . ?
O1 Ni1 O2 C1 170.9(5) . . . . ?
O1 Ni1 N1 C13 178.0(4) . . . . ?
O1 Ni1 N1 C14 -5.9(5) . . . . ?
O2 Ni1 O1 C20 -174.1(5) . . . . ?
O2 Ni1 N2 C7 8.7(5) . . . . ?
O2 Ni1 N2 C8 -175.6(4) . . . . ?
O2 C1 C2 C3 179.8(5) . . . . ?
O2 C1 C6 C5 -179.7(5) . . . . ?
O2 C1 C6 C7 2.8(9) . . . . ?
N1 Ni1 O1 C20 6.2(5) . . . . ?
N1 Ni1 N2 C7 -171.6(5) . . . . ?
N1 Ni1 N2 C8 4.0(4) . . . . ?
N1 C14 C15 C16 -178.3(5) . . . . ?
N1 C14 C15 C20 0.8(9) . . . . ?
N2 Ni1 O2 C1 -8.0(5) . . . . ?
N2 Ni1 N1 C13 -3.1(4) . . . . ?
N2 Ni1 N1 C14 173.0(5) . . . . ?
N2 C8 C9 C10 177.1(6) . . . . ?
N2 C8 C13 N1 1.7(7) . . . . ?
N2 C8 C13 C12 -178.5(5) . . . . ?
C1 C2 C3 C4 -0.4(10) . . . . ?
C1 C6 C7 N2 -1.8(9) . . . . ?
C2 C1 C6 C5 0.9(8) . . . . ?
C2 C1 C6 C7 -176.6(5) . . . . ?
C2 C3 C4 C5 1.5(10) . . . . ?
C3 C4 C5 C6 -1.4(10) . . . . ?
C4 C5 C6 C1 0.2(9) . . . . ?
C4 C5 C6 C7 177.7(6) . . . . ?
C5 C6 C7 N2 -179.3(5) . . . . ?
C6 C1 C2 C3 -0.8(9) . . . . ?
C7 N2 C8 C9 -8.1(9) . . . . ?
C7 N2 C8 C13 171.7(5) . . . . ?
C8 N2 C7 C6 179.2(5) . . . . ?
C8 C9 C10 C11 2.1(10) . . . . ?
C9 C8 C13 N1 -178.4(5) . . . . ?
C9 C8 C13 C12 1.3(9) . . . . ?
C9 C10 C11 C12 -0.2(10) . . . . ?
C10 C11 C12 C13 -1.2(10) . . . . ?
C11 C12 C13 N1 -179.7(6) . . . . ?
C11 C12 C13 C8 0.6(9) . . . . ?
C13 N1 C14 C15 179.4(5) . . . . ?
C13 C8 C9 C10 -2.7(9) . . . . ?
C14 N1 C13 C8 -174.8(5) . . . . ?
C14 N1 C13 C12 5.4(8) . . . . ?
C14 C15 C16 C17 179.7(6) . . . . ?
C14 C15 C20 O1 -0.7(9) . . . . ?
C14 C15 C20 C19 -179.6(5) . . . . ?
C15 C16 C17 C18 -0.5(10) . . . . ?
C16 C15 C20 O1 178.4(5) . . . . ?
C16 C15 C20 C19 -0.5(8) . . . . ?
C16 C17 C18 C19 0.4(10) . . . . ?
C17 C18 C19 C20 -0.3(10) . . . . ?
C18 C19 C20 O1 -178.6(5) . . . . ?
C18 C19 C20 C15 0.3(9) . . . . ?
C20 C15 C16 C17 0.6(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 
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data_22gtu446_hd_4_0m
_database_code_depnum_ccdc_archive 'CCDC 2312405'
loop_
_audit_author_name
_audit_author_address
'Yunus Zorlu'
;Gebze Technical University
Turkey
;
_audit_update_record             
;
2023-12-06 deposited with the CCDC.	2024-05-09 downloaded from the CCDC.
;
_audit_creation_date             2023-02-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 N2 Ni O2'
_chemical_formula_sum            'C16 H14 N2 Ni O2'
_chemical_formula_weight         325.00
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   7.4650(14)
_cell_length_b                   13.788(3)
_cell_length_c                   26.074(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2683.8(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2327
_cell_measurement_temperature    298
_cell_measurement_theta_max      20.38
_cell_measurement_theta_min      2.95
_shelx_estimated_absorpt_T_max   0.903
_shelx_estimated_absorpt_T_min   0.795
_exptl_absorpt_coefficient_mu    1.451
_exptl_absorpt_correction_T_max  0.7222
_exptl_absorpt_correction_T_min  0.6770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0691 before and 0.0615 after correction.
The Ratio of minimum to maximum transmission is 0.9374.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.166
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.072
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0792
_diffrn_reflns_av_unetI/netI     0.0362
_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       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            27110
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.993
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         1.562
_diffrn_ambient_temperature      298
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 microsource'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1622
_reflns_number_total             2359
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2359
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0326
_refine_ls_restrained_S_all      1.058
_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)+(0.0359P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0729
_refine_ls_wR_factor_ref         0.0797
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.69054(4) 0.54793(2) 0.51144(2) 0.03153(14) Uani 1 1 d . . . . .
O1 O 0.6166(2) 0.63711(11) 0.55980(7) 0.0366(5) Uani 1 1 d . . . . .
O2 O 0.5971(2) 0.63342(11) 0.46413(8) 0.0352(5) Uani 1 1 d . . . . .
N1 N 0.7905(3) 0.46428(14) 0.55881(10) 0.0353(6) Uani 1 1 d . . . . .
N2 N 0.7577(3) 0.45843(15) 0.46250(11) 0.0374(6) Uani 1 1 d . . . . .
C1 C 0.7964(3) 0.47535(19) 0.60771(13) 0.0403(8) Uani 1 1 d . . . . .
H1 H 0.855365 0.427907 0.626615 0.048 Uiso 1 1 calc R U . . .
C2 C 0.7200(4) 0.55422(19) 0.63535(12) 0.0380(7) Uani 1 1 d . . . . .
C3 C 0.7286(4) 0.5545(2) 0.68900(13) 0.0570(9) Uani 1 1 d . . . . .
H3 H 0.793113 0.506072 0.705595 0.068 Uiso 1 1 calc R U . . .
C4 C 0.6453(5) 0.6237(3) 0.71750(13) 0.0636(10) Uani 1 1 d . . . . .
H4 H 0.655100 0.623631 0.753060 0.076 Uiso 1 1 calc R U . . .
C5 C 0.5452(4) 0.6947(2) 0.69264(13) 0.0536(9) Uani 1 1 d . . . . .
H5 H 0.484155 0.740892 0.711863 0.064 Uiso 1 1 calc R U . . .
C6 C 0.5356(4) 0.69730(19) 0.64047(12) 0.0416(7) Uani 1 1 d . . . . .
H6 H 0.467871 0.745419 0.624712 0.050 Uiso 1 1 calc R U . . .
C7 C 0.6259(3) 0.62889(18) 0.60989(11) 0.0332(7) Uani 1 1 d . . . . .
C8 C 0.6107(3) 0.62946(18) 0.41415(12) 0.0360(7) Uani 1 1 d . . . . .
C9 C 0.5276(4) 0.70138(19) 0.38412(12) 0.0413(7) Uani 1 1 d . . . . .
H9 H 0.460246 0.749147 0.400317 0.050 Uiso 1 1 calc R U . . .
C10 C 0.5428(4) 0.7032(2) 0.33209(13) 0.0548(9) Uani 1 1 d . . . . .
H10 H 0.486498 0.751967 0.313486 0.066 Uiso 1 1 calc R U . . .
C11 C 0.6415(5) 0.6329(3) 0.30656(13) 0.0660(10) Uani 1 1 d . . . . .
H11 H 0.655691 0.636000 0.271160 0.079 Uiso 1 1 calc R U . . .
C12 C 0.7172(4) 0.5596(2) 0.33383(13) 0.0583(9) Uani 1 1 d . . . . .
H12 H 0.779510 0.511256 0.316520 0.070 Uiso 1 1 calc R U . . .
C13 C 0.7035(4) 0.55500(19) 0.38761(12) 0.0399(7) Uani 1 1 d . . . . .
C14 C 0.7635(4) 0.4710(2) 0.41377(13) 0.0417(8) Uani 1 1 d . . . . .
H14 H 0.810895 0.420944 0.394055 0.050 Uiso 1 1 calc R U . . .
C15 C 0.7963(4) 0.36208(19) 0.48438(12) 0.0464(8) Uani 1 1 d . . . . .
H15A H 0.879914 0.327295 0.462655 0.056 Uiso 1 1 calc R U . . .
H15B H 0.686945 0.324380 0.486974 0.056 Uiso 1 1 calc R U . . .
C16 C 0.8752(4) 0.37738(18) 0.53621(12) 0.0448(8) Uani 1 1 d . . . . .
H16A H 0.853042 0.321234 0.557712 0.054 Uiso 1 1 calc R U . . .
H16B H 1.003617 0.386732 0.533517 0.054 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 O1 1.8458(18) . ?
Ni1 O2 1.8435(18) . ?
Ni1 N1 1.847(2) . ?
Ni1 N2 1.844(2) . ?
O1 C7 1.313(3) . ?
O2 C8 1.308(3) . ?
N1 C1 1.285(4) . ?
N1 C16 1.477(3) . ?
N2 C14 1.283(4) . ?
N2 C15 1.474(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.424(4) . ?
C2 C3 1.400(4) . ?
C2 C7 1.412(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.360(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.391(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.363(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.407(4) . ?
C8 C9 1.407(4) . ?
C8 C13 1.419(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.362(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.387(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.359(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.407(4) . ?
C13 C14 1.417(4) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.489(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?

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
O1 Ni1 N1 94.58(10) . . ?
O2 Ni1 O1 85.29(8) . . ?
O2 Ni1 N1 178.30(9) . . ?
O2 Ni1 N2 93.89(10) . . ?
N2 Ni1 O1 178.35(9) . . ?
N2 Ni1 N1 86.28(11) . . ?
C7 O1 Ni1 127.33(16) . . ?
C8 O2 Ni1 127.62(16) . . ?
C1 N1 Ni1 127.09(19) . . ?
C1 N1 C16 118.5(2) . . ?
C16 N1 Ni1 114.4(2) . . ?
C14 N2 Ni1 127.2(2) . . ?
C14 N2 C15 119.9(2) . . ?
C15 N2 Ni1 112.8(2) . . ?
N1 C1 H1 117.3 . . ?
N1 C1 C2 125.4(3) . . ?
C2 C1 H1 117.3 . . ?
C3 C2 C1 119.3(3) . . ?
C3 C2 C7 119.4(3) . . ?
C7 C2 C1 121.2(3) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 C2 121.8(3) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.0(3) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 119.2 . . ?
C5 C6 C7 121.5(3) . . ?
C7 C6 H6 119.2 . . ?
O1 C7 C2 123.8(2) . . ?
O1 C7 C6 118.7(2) . . ?
C6 C7 C2 117.4(3) . . ?
O2 C8 C9 119.4(3) . . ?
O2 C8 C13 123.6(3) . . ?
C9 C8 C13 117.0(3) . . ?
C8 C9 H9 119.0 . . ?
C10 C9 C8 122.0(3) . . ?
C10 C9 H9 119.0 . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.7(3) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.4 . . ?
C12 C11 C10 119.3(3) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 H12 119.2 . . ?
C11 C12 C13 121.7(3) . . ?
C13 C12 H12 119.2 . . ?
C12 C13 C8 119.2(3) . . ?
C12 C13 C14 119.6(3) . . ?
C14 C13 C8 120.7(3) . . ?
N2 C14 C13 125.2(3) . . ?
N2 C14 H14 117.4 . . ?
C13 C14 H14 117.4 . . ?
N2 C15 H15A 110.2 . . ?
N2 C15 H15B 110.2 . . ?
N2 C15 C16 107.5(2) . . ?
H15A C15 H15B 108.5 . . ?
C16 C15 H15A 110.2 . . ?
C16 C15 H15B 110.2 . . ?
N1 C16 C15 107.9(2) . . ?
N1 C16 H16A 110.1 . . ?
N1 C16 H16B 110.1 . . ?
C15 C16 H16A 110.1 . . ?
C15 C16 H16B 110.1 . . ?
H16A C16 H16B 108.4 . . ?

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 O1 C7 C2 9.7(4) . . . . ?
Ni1 O1 C7 C6 -169.48(17) . . . . ?
Ni1 O2 C8 C9 179.21(17) . . . . ?
Ni1 O2 C8 C13 0.2(4) . . . . ?
Ni1 N1 C1 C2 2.3(4) . . . . ?
Ni1 N1 C16 C15 -21.8(3) . . . . ?
Ni1 N2 C14 C13 -5.9(4) . . . . ?
Ni1 N2 C15 C16 -33.6(3) . . . . ?
O1 Ni1 O2 C8 172.0(2) . . . . ?
O1 Ni1 N1 C1 -0.3(2) . . . . ?
O1 Ni1 N1 C16 -178.75(18) . . . . ?
O2 Ni1 O1 C7 176.1(2) . . . . ?
O2 Ni1 N2 C14 12.3(2) . . . . ?
O2 Ni1 N2 C15 -163.79(19) . . . . ?
O2 C8 C9 C10 177.4(2) . . . . ?
O2 C8 C13 C12 -177.2(3) . . . . ?
O2 C8 C13 C14 10.3(4) . . . . ?
N1 Ni1 O1 C7 -5.6(2) . . . . ?
N1 Ni1 N2 C14 -166.0(3) . . . . ?
N1 Ni1 N2 C15 17.9(2) . . . . ?
N1 C1 C2 C3 176.8(3) . . . . ?
N1 C1 C2 C7 0.9(4) . . . . ?
N2 Ni1 O2 C8 -9.5(2) . . . . ?
N2 Ni1 N1 C1 -178.9(2) . . . . ?
N2 Ni1 N1 C16 2.66(18) . . . . ?
N2 C15 C16 N1 33.9(3) . . . . ?
C1 N1 C16 C15 159.7(2) . . . . ?
C1 C2 C3 C4 -174.5(3) . . . . ?
C1 C2 C7 O1 -7.0(4) . . . . ?
C1 C2 C7 C6 172.2(2) . . . . ?
C2 C3 C4 C5 1.6(5) . . . . ?
C3 C2 C7 O1 177.0(3) . . . . ?
C3 C2 C7 C6 -3.8(4) . . . . ?
C3 C4 C5 C6 -2.4(5) . . . . ?
C4 C5 C6 C7 0.0(4) . . . . ?
C5 C6 C7 O1 -177.7(3) . . . . ?
C5 C6 C7 C2 3.1(4) . . . . ?
C7 C2 C3 C4 1.5(5) . . . . ?
C8 C9 C10 C11 0.3(4) . . . . ?
C8 C13 C14 N2 -7.5(4) . . . . ?
C9 C8 C13 C12 3.7(4) . . . . ?
C9 C8 C13 C14 -168.7(3) . . . . ?
C9 C10 C11 C12 2.7(5) . . . . ?
C10 C11 C12 C13 -2.4(5) . . . . ?
C11 C12 C13 C8 -0.9(5) . . . . ?
C11 C12 C13 C14 171.6(3) . . . . ?
C12 C13 C14 N2 -179.9(3) . . . . ?
C13 C8 C9 C10 -3.5(4) . . . . ?
C14 N2 C15 C16 150.0(3) . . . . ?
C15 N2 C14 C13 169.9(3) . . . . ?
C16 N1 C1 C2 -179.3(2) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
