# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_ma33_A
_database_code_depnum_ccdc_archive 'CCDC 1954803'
loop_
_audit_author_name
_audit_author_address
'Anna Kozakiewicz'
;Faculty of Chemistry, Nicolaus Copernicus University in Torun
Poland
;
_audit_update_record             
;
2019-09-19 deposited with the CCDC.	2019-11-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H15 Cl N2 Ni O2'
_chemical_formula_sum            'C21 H15 Cl N2 Ni O2'
_chemical_formula_weight         421.51

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'
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'

_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                   11.0230(14)
_cell_length_b                   8.0024(8)
_cell_length_c                   19.532(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.302(12)
_cell_angle_gamma                90
_cell_volume                     1653.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    1011
_cell_measurement_theta_min      2.7590
_cell_measurement_theta_max      19.7060

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.693
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.191
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.022
_exptl_absorpt_coefficient_mu    1.355
_shelx_estimated_absorpt_T_min   0.782
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.75684
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'Oxford Diffraction CrysAlis'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Oxford Sapphire CCD'
_diffrn_measurement_method       θ/2θ
_diffrn_detector_area_resol_mean 8.2564
_diffrn_reflns_number            12101
_diffrn_reflns_av_unetI/netI     0.3140
_diffrn_reflns_av_R_equivalents  0.2147
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.925
_diffrn_reflns_theta_max         28.389
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3825
_reflns_number_gt                1214
_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       'Oxford Diffraction CrysAlis'
_computing_cell_refinement       'Oxford Diffraction CrysAlis'
_computing_data_reduction        'Oxford Diffraction CrysAlis'
_computing_structure_solution    'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'CIFTAB (Sheldrick, 2014)'

_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)+(0.1293P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3825
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2877
_refine_ls_R_factor_gt           0.0944
_refine_ls_wR_factor_ref         0.3456
_refine_ls_wR_factor_gt          0.2181
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.988
_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_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 0.54606(13) 0.33322(17) 0.46617(7) 0.0568(6) Uani 1 1 d . . . . .
O1 O 0.5301(8) 0.4089(10) 0.3754(4) 0.066(2) Uani 1 1 d . . . . .
C2 C 0.6061(13) 0.5006(15) 0.3545(6) 0.064(3) Uani 1 1 d . . . . .
C3 C 0.5734(14) 0.5574(16) 0.2810(7) 0.086(4) Uani 1 1 d . . . . .
H3A H 0.4968 0.5251 0.2497 0.103 Uiso 1 1 calc R U . . .
C4 C 0.654(2) 0.6590(18) 0.2567(9) 0.108(6) Uani 1 1 d . . . . .
H4A H 0.6295 0.6965 0.2098 0.129 Uiso 1 1 calc R U . . .
C5 C 0.7706(18) 0.706(2) 0.3000(10) 0.106(5) Uani 1 1 d . . . . .
H5A H 0.8253 0.7700 0.2821 0.127 Uiso 1 1 calc R U . . .
C6 C 0.8033(15) 0.6586(16) 0.3677(8) 0.090(4) Uani 1 1 d . . . . .
H6A H 0.8805 0.6939 0.3975 0.108 Uiso 1 1 calc R U . . .
C7 C 0.7258(13) 0.5573(15) 0.3956(7) 0.071(3) Uani 1 1 d . . . . .
C8 C 0.7645(11) 0.5202(14) 0.4710(6) 0.068(3) Uani 1 1 d . . . . .
H8A H 0.8429 0.5600 0.4975 0.081 Uiso 1 1 calc R U . . .
N9 N 0.6989(8) 0.4361(10) 0.5050(4) 0.053(2) Uani 1 1 d . . . . .
C10 C 0.7487(12) 0.4096(13) 0.5808(6) 0.059(3) Uani 1 1 d . . . . .
C11 C 0.8604(12) 0.4795(15) 0.6251(7) 0.076(4) Uani 1 1 d . . . . .
H11A H 0.9104 0.5500 0.6065 0.092 Uiso 1 1 calc R U . . .
C12 C 0.8933(13) 0.4410(17) 0.6959(7) 0.081(4) Uani 1 1 d . . . . .
C13 C 0.8156(14) 0.3420(17) 0.7231(6) 0.080(4) Uani 1 1 d . . . . .
Cl1 Cl 0.8635(4) 0.3008(7) 0.8127(2) 0.1343(18) Uani 1 1 d . . . . .
C14 C 0.7078(11) 0.2745(14) 0.6805(6) 0.065(3) Uani 1 1 d . . . . .
H14A H 0.6580 0.2049 0.6996 0.078 Uiso 1 1 calc R U . . .
C15 C 0.6724(11) 0.3102(13) 0.6080(6) 0.058(3) Uani 1 1 d . . . . .
N16 N 0.5616(9) 0.2528(11) 0.5570(4) 0.058(2) Uani 1 1 d . . . . .
C17 C 0.4809(11) 0.1559(14) 0.5751(6) 0.061(3) Uani 1 1 d . . . . .
H17A H 0.5005 0.1234 0.6226 0.073 Uiso 1 1 calc R U . . .
C18 C 0.3671(11) 0.0958(13) 0.5297(6) 0.059(3) Uani 1 1 d . . . . .
C19 C 0.2901(13) -0.0042(15) 0.5563(7) 0.076(4) Uani 1 1 d . . . . .
H19A H 0.3167 -0.0355 0.6040 0.091 Uiso 1 1 calc R U . . .
C20 C 0.1745(14) -0.0603(16) 0.5147(9) 0.089(4) Uani 1 1 d . . . . .
H20A H 0.1237 -0.1274 0.5341 0.107 Uiso 1 1 calc R U . . .
C21 C 0.1349(13) -0.0139(17) 0.4420(8) 0.085(4) Uani 1 1 d . . . . .
H21A H 0.0573 -0.0511 0.4134 0.102 Uiso 1 1 calc R U . . .
C22 C 0.2084(13) 0.0841(16) 0.4136(7) 0.076(4) Uani 1 1 d . . . . .
H22A H 0.1806 0.1120 0.3655 0.092 Uiso 1 1 calc R U . . .
C23 C 0.3265(12) 0.1451(14) 0.4552(6) 0.059(3) Uani 1 1 d . . . . .
O24 O 0.3952(7) 0.2331(9) 0.4250(4) 0.063(2) Uani 1 1 d . . . . .
C25 C 1.0000(14) 0.514(2) 0.7533(8) 0.130(6) Uani 1 1 d . . . . .
H25A H 1.0016 0.4646 0.7983 0.195 Uiso 1 1 calc R U . . .
H25B H 1.0785 0.4923 0.7428 0.195 Uiso 1 1 calc R U . . .
H25C H 0.9881 0.6328 0.7557 0.195 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 O24 1.817(8) . ?
Ni1 O1 1.834(7) . ?
Ni1 N9 1.837(9) . ?
Ni1 N16 1.849(9) . ?
O1 C2 1.265(14) . ?
C2 C7 1.413(16) . ?
C2 C3 1.451(15) . ?
C3 C4 1.387(19) . ?
C3 H3A 0.9300 . ?
C4 C5 1.37(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.324(19) . ?
C5 H5A 0.9300 . ?
C6 C7 1.395(17) . ?
C6 H6A 0.9300 . ?
C7 C8 1.445(16) . ?
C8 N9 1.298(14) . ?
C8 H8A 0.9300 . ?
N9 C10 1.443(13) . ?
C10 C15 1.369(15) . ?
C10 C11 1.406(15) . ?
C11 C12 1.363(16) . ?
C11 H11A 0.9300 . ?
C12 C13 1.378(18) . ?
C12 C25 1.498(17) . ?
C13 C14 1.358(16) . ?
C13 Cl1 1.711(12) . ?
C14 C15 1.388(14) . ?
C14 H14A 0.9300 . ?
C15 N16 1.418(13) . ?
N16 C17 1.302(14) . ?
C17 C18 1.402(15) . ?
C17 H17A 0.9300 . ?
C18 C19 1.370(15) . ?
C18 C23 1.451(15) . ?
C19 C20 1.380(16) . ?
C19 H19A 0.9300 . ?
C20 C21 1.412(17) . ?
C20 H20A 0.9300 . ?
C21 C22 1.354(17) . ?
C21 H21A 0.9300 . ?
C22 C23 1.415(16) . ?
C22 H22A 0.9300 . ?
C23 O24 1.292(13) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

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
O24 Ni1 O1 83.7(3) . . ?
O24 Ni1 N9 178.2(4) . . ?
O1 Ni1 N9 94.5(4) . . ?
O24 Ni1 N16 95.6(4) . . ?
O1 Ni1 N16 178.9(4) . . ?
N9 Ni1 N16 86.1(4) . . ?
C2 O1 Ni1 127.7(7) . . ?
O1 C2 C7 126.9(11) . . ?
O1 C2 C3 119.9(13) . . ?
C7 C2 C3 113.3(13) . . ?
C4 C3 C2 121.1(14) . . ?
C4 C3 H3A 119.4 . . ?
C2 C3 H3A 119.4 . . ?
C5 C4 C3 121.9(15) . . ?
C5 C4 H4A 119.0 . . ?
C3 C4 H4A 119.0 . . ?
C6 C5 C4 118.7(17) . . ?
C6 C5 H5A 120.6 . . ?
C4 C5 H5A 120.6 . . ?
C5 C6 C7 122.1(16) . . ?
C5 C6 H6A 118.9 . . ?
C7 C6 H6A 118.9 . . ?
C6 C7 C2 122.7(13) . . ?
C6 C7 C8 118.7(13) . . ?
C2 C7 C8 118.3(12) . . ?
N9 C8 C7 125.5(11) . . ?
N9 C8 H8A 117.3 . . ?
C7 C8 H8A 117.3 . . ?
C8 N9 C10 119.6(10) . . ?
C8 N9 Ni1 126.8(8) . . ?
C10 N9 Ni1 113.5(8) . . ?
C15 C10 C11 121.4(11) . . ?
C15 C10 N9 112.6(10) . . ?
C11 C10 N9 126.0(12) . . ?
C12 C11 C10 118.1(13) . . ?
C12 C11 H11A 120.9 . . ?
C10 C11 H11A 120.9 . . ?
C11 C12 C13 120.3(12) . . ?
C11 C12 C25 127.0(16) . . ?
C13 C12 C25 112.2(13) . . ?
C14 C13 C12 121.6(12) . . ?
C14 C13 Cl1 121.1(12) . . ?
C12 C13 Cl1 117.3(11) . . ?
C13 C14 C15 119.4(13) . . ?
C13 C14 H14A 120.3 . . ?
C15 C14 H14A 120.3 . . ?
C10 C15 C14 119.2(11) . . ?
C10 C15 N16 114.7(10) . . ?
C14 C15 N16 126.1(11) . . ?
C17 N16 C15 121.5(10) . . ?
C17 N16 Ni1 125.5(8) . . ?
C15 N16 Ni1 113.0(8) . . ?
N16 C17 C18 126.3(11) . . ?
N16 C17 H17A 116.9 . . ?
C18 C17 H17A 116.9 . . ?
C19 C18 C17 120.0(12) . . ?
C19 C18 C23 119.3(12) . . ?
C17 C18 C23 120.6(11) . . ?
C18 C19 C20 122.3(13) . . ?
C18 C19 H19A 118.8 . . ?
C20 C19 H19A 118.8 . . ?
C19 C20 C21 118.7(14) . . ?
C19 C20 H20A 120.6 . . ?
C21 C20 H20A 120.6 . . ?
C22 C21 C20 120.8(13) . . ?
C22 C21 H21A 119.6 . . ?
C20 C21 H21A 119.6 . . ?
C21 C22 C23 121.6(13) . . ?
C21 C22 H22A 119.2 . . ?
C23 C22 H22A 119.2 . . ?
O24 C23 C22 119.2(11) . . ?
O24 C23 C18 123.5(11) . . ?
C22 C23 C18 117.3(12) . . ?
C23 O24 Ni1 128.2(7) . . ?
C12 C25 H25A 109.5 . . ?
C12 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C12 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
O24 Ni1 O1 C2 -179.8(10) . . . . ?
N9 Ni1 O1 C2 -0.1(10) . . . . ?
Ni1 O1 C2 C7 4.6(17) . . . . ?
Ni1 O1 C2 C3 -175.9(8) . . . . ?
O1 C2 C3 C4 179.5(11) . . . . ?
C7 C2 C3 C4 -0.9(16) . . . . ?
C2 C3 C4 C5 2(2) . . . . ?
C3 C4 C5 C6 -3(2) . . . . ?
C4 C5 C6 C7 3(2) . . . . ?
C5 C6 C7 C2 -1(2) . . . . ?
C5 C6 C7 C8 -175.9(13) . . . . ?
O1 C2 C7 C6 180.0(11) . . . . ?
C3 C2 C7 C6 0.4(16) . . . . ?
O1 C2 C7 C8 -5.4(17) . . . . ?
C3 C2 C7 C8 175.0(9) . . . . ?
C6 C7 C8 N9 175.9(11) . . . . ?
C2 C7 C8 N9 1.1(17) . . . . ?
C7 C8 N9 C10 -179.4(10) . . . . ?
C7 C8 N9 Ni1 3.7(16) . . . . ?
O1 Ni1 N9 C8 -3.8(10) . . . . ?
N16 Ni1 N9 C8 175.3(10) . . . . ?
O1 Ni1 N9 C10 179.1(6) . . . . ?
N16 Ni1 N9 C10 -1.7(7) . . . . ?
C8 N9 C10 C15 -176.2(10) . . . . ?
Ni1 N9 C10 C15 1.2(11) . . . . ?
C8 N9 C10 C11 5.9(15) . . . . ?
Ni1 N9 C10 C11 -176.8(9) . . . . ?
C15 C10 C11 C12 2.2(17) . . . . ?
N9 C10 C11 C12 179.9(10) . . . . ?
C10 C11 C12 C13 -2.7(19) . . . . ?
C10 C11 C12 C25 -173.3(12) . . . . ?
C11 C12 C13 C14 3(2) . . . . ?
C25 C12 C13 C14 174.7(12) . . . . ?
C11 C12 C13 Cl1 -179.6(10) . . . . ?
C25 C12 C13 Cl1 -7.7(16) . . . . ?
C12 C13 C14 C15 -2.2(18) . . . . ?
Cl1 C13 C14 C15 -179.7(9) . . . . ?
C11 C10 C15 C14 -1.6(16) . . . . ?
N9 C10 C15 C14 -179.6(9) . . . . ?
C11 C10 C15 N16 178.5(9) . . . . ?
N9 C10 C15 N16 0.4(13) . . . . ?
C13 C14 C15 C10 1.6(16) . . . . ?
C13 C14 C15 N16 -178.5(10) . . . . ?
C10 C15 N16 C17 179.4(10) . . . . ?
C14 C15 N16 C17 -0.6(16) . . . . ?
C10 C15 N16 Ni1 -1.8(11) . . . . ?
C14 C15 N16 Ni1 178.3(8) . . . . ?
O24 Ni1 N16 C17 0.4(9) . . . . ?
N9 Ni1 N16 C17 -179.3(9) . . . . ?
O24 Ni1 N16 C15 -178.4(7) . . . . ?
N9 Ni1 N16 C15 2.0(7) . . . . ?
C15 N16 C17 C18 178.1(9) . . . . ?
Ni1 N16 C17 C18 -0.6(15) . . . . ?
N16 C17 C18 C19 -179.3(11) . . . . ?
N16 C17 C18 C23 -2.3(16) . . . . ?
C17 C18 C19 C20 176.9(10) . . . . ?
C23 C18 C19 C20 -0.1(17) . . . . ?
C18 C19 C20 C21 0.5(18) . . . . ?
C19 C20 C21 C22 -0.2(19) . . . . ?
C20 C21 C22 C23 -1(2) . . . . ?
C21 C22 C23 O24 177.5(11) . . . . ?
C21 C22 C23 C18 1.1(17) . . . . ?
C19 C18 C23 O24 -176.9(10) . . . . ?
C17 C18 C23 O24 6.1(16) . . . . ?
C19 C18 C23 C22 -0.8(16) . . . . ?
C17 C18 C23 C22 -177.7(10) . . . . ?
C22 C23 O24 Ni1 177.1(7) . . . . ?
C18 C23 O24 Ni1 -6.8(15) . . . . ?
O1 Ni1 O24 C23 -177.6(9) . . . . ?
N16 Ni1 O24 C23 3.3(9) . . . . ?

_refine_diff_density_max         0.532
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.170

_shelxl_version_number           2014-3

