# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2129543'
loop_
_audit_author_name
_audit_author_address
'Magda Monari'
;University of Bologna
Italy
;
_audit_update_record             
;
2021-12-17 deposited with the CCDC.	2022-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 Cl2 N2 Ni O2'
_chemical_formula_weight         427.98

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'
Cl Cl 0.1484 0.1585 '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'

_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'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.797(3)
_cell_length_b                   12.158(4)
_cell_length_c                   19.362(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2070.8(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9897
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      28.28

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.81
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    1.207
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6257
_exptl_absorpt_correction_T_max  0.7687
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26173
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.129
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3843
_reflns_number_gt                3618
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0582P)²+0.6417P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1389 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.028(6)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3843
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.0968
_refine_ls_wR_factor_gt          0.0947
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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
Ni Ni 0.59227(7) 0.44993(5) 0.35755(3) 0.05199(19) Uani 1 1 d . . . . .
Cl1 Cl 0.39278(17) 0.34071(11) 0.35624(8) 0.0779(4) Uani 1 1 d . . . . .
Cl2 Cl 0.78801(18) 0.44500(15) 0.28698(7) 0.0921(6) Uani 1 1 d . . . . .
O1 O 0.5943(4) 0.7875(2) 0.50916(16) 0.0531(7) Uani 1 1 d . . . . .
O2 O 0.4670(3) 0.6367(3) 0.57916(14) 0.0537(8) Uani 1 1 d . . . . .
N2 N 0.6541(4) 0.4653(3) 0.45643(17) 0.0434(8) Uani 1 1 d . . . . .
N1 N 0.5129(4) 0.6019(3) 0.37151(16) 0.0451(8) Uani 1 1 d . . . . .
C12 C 0.5894(4) 0.5553(3) 0.48560(17) 0.0375(7) Uani 1 1 d . . . . .
C6 C 0.5413(4) 0.6399(3) 0.43564(19) 0.0379(8) Uani 1 1 d . . . . .
C11 C 0.5636(4) 0.5601(3) 0.55658(19) 0.0429(9) Uani 1 1 d . . . . .
C2 C 0.4595(6) 0.6679(4) 0.3220(2) 0.0599(13) Uani 1 1 d . . . . .
C5 C 0.5335(4) 0.7528(3) 0.4504(2) 0.0450(9) Uani 1 1 d . . . . .
C10 C 0.6335(6) 0.4800(4) 0.5974(2) 0.0562(12) Uani 1 1 d . . . . .
H10 H 0.628242 0.484603 0.645289 0.067 Uiso 1 1 calc R U . . .
C8 C 0.7129(6) 0.3857(4) 0.4959(3) 0.0581(12) Uani 1 1 d . . . . .
C9 C 0.7089(6) 0.3954(4) 0.5672(3) 0.0645(13) Uani 1 1 d . . . . .
H9 H 0.758166 0.343548 0.594516 0.077 Uiso 1 1 calc R U . . .
C17 C 0.4718(6) 0.6735(5) 0.6511(2) 0.0676(14) Uani 1 1 d . . . . .
H17 H 0.574329 0.663264 0.669879 0.081 Uiso 1 1 calc R U . . .
C3 C 0.4332(6) 0.7776(4) 0.3359(3) 0.0701(15) Uani 1 1 d . . . . .
H3 H 0.389820 0.822683 0.302429 0.084 Uiso 1 1 calc R U . . .
C4 C 0.4710(5) 0.8195(4) 0.3988(3) 0.0612(13) Uani 1 1 d . . . . .
H4 H 0.454969 0.893815 0.407662 0.073 Uiso 1 1 calc R U . . .
C15 C 0.5470(7) 0.8723(5) 0.6180(3) 0.0856(19) Uani 1 1 d . . . . .
H15A H 0.535109 0.943735 0.639601 0.103 Uiso 1 1 calc R U . . .
H15B H 0.648214 0.846149 0.629203 0.103 Uiso 1 1 calc R U . . .
C18 C 0.4318(7) 0.7934(6) 0.6512(3) 0.089(2) Uani 1 1 d . . . . .
H18A H 0.416520 0.816169 0.698706 0.106 Uiso 1 1 calc R U . . .
H18B H 0.335451 0.802072 0.627456 0.106 Uiso 1 1 calc R U . . .
C16 C 0.3593(7) 0.6041(7) 0.6914(3) 0.098(2) Uani 1 1 d . . . . .
H16A H 0.260281 0.610935 0.670991 0.147 Uiso 1 1 calc R U . . .
H16B H 0.355776 0.628985 0.738406 0.147 Uiso 1 1 calc R U . . .
H16C H 0.390661 0.528521 0.690189 0.147 Uiso 1 1 calc R U . . .
C14 C 0.5388(6) 0.8882(4) 0.5409(3) 0.0701(15) Uani 1 1 d . . . . .
H14 H 0.432944 0.900448 0.527199 0.084 Uiso 1 1 calc R U . . .
C13 C 0.6361(7) 0.9844(5) 0.5165(4) 0.099(2) Uani 1 1 d . . . . .
H13A H 0.737314 0.976661 0.534455 0.149 Uiso 1 1 calc R U . . .
H13B H 0.592811 1.052075 0.532777 0.149 Uiso 1 1 calc R U . . .
H13C H 0.639568 0.985032 0.466957 0.149 Uiso 1 1 calc R U . . .
C7 C 0.7814(8) 0.2864(4) 0.4596(3) 0.0879(19) Uani 1 1 d . . . . .
H7A H 0.701663 0.237082 0.445882 0.132 Uiso 1 1 calc R U . . .
H7B H 0.849445 0.249090 0.490498 0.132 Uiso 1 1 calc R U . . .
H7C H 0.836421 0.310204 0.419448 0.132 Uiso 1 1 calc R U . . .
C1 C 0.4310(10) 0.6179(6) 0.2523(3) 0.098(2) Uani 1 1 d . . . . .
H1A H 0.526225 0.605578 0.229353 0.148 Uiso 1 1 calc R U . . .
H1B H 0.369786 0.666980 0.225208 0.148 Uiso 1 1 calc R U . . .
H1C H 0.378741 0.549115 0.257788 0.148 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
Ni N1 1.993(4) . ?
Ni N2 1.999(3) . ?
Ni Cl2 2.1990(15) . ?
Ni Cl1 2.2007(14) . ?
O1 C5 1.326(5) . ?
O1 C14 1.453(5) . ?
O2 C11 1.334(5) . ?
O2 C17 1.465(5) . ?
N2 C8 1.337(6) . ?
N2 C12 1.356(5) . ?
N1 C6 1.348(5) . ?
N1 C2 1.335(6) . ?
C12 C11 1.394(5) . ?
C12 C6 1.474(5) . ?
C6 C5 1.404(6) . ?
C11 C10 1.397(6) . ?
C2 C3 1.381(8) . ?
C2 C1 1.501(7) . ?
C5 C4 1.399(6) . ?
C10 C9 1.356(7) . ?
C10 H10 0.9300 . ?
C8 C9 1.387(7) . ?
C8 C7 1.522(7) . ?
C9 H9 0.9300 . ?
C17 C18 1.499(9) . ?
C17 C16 1.516(9) . ?
C17 H17 0.9800 . ?
C3 C4 1.362(8) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C15 C14 1.507(9) . ?
C15 C18 1.536(10) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C14 C13 1.525(8) . ?
C14 H14 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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
N1 Ni N2 83.02(13) . . ?
N1 Ni Cl2 112.56(11) . . ?
N2 Ni Cl2 112.61(11) . . ?
N1 Ni Cl1 106.36(11) . . ?
N2 Ni Cl1 106.53(11) . . ?
Cl2 Ni Cl1 126.93(6) . . ?
C5 O1 C14 119.7(4) . . ?
C11 O2 C17 120.4(3) . . ?
C8 N2 C12 120.5(4) . . ?
C8 N2 Ni 125.8(3) . . ?
C12 N2 Ni 111.1(2) . . ?
C6 N1 C2 121.3(4) . . ?
C6 N1 Ni 112.2(3) . . ?
C2 N1 Ni 125.6(3) . . ?
N2 C12 C11 120.9(3) . . ?
N2 C12 C6 114.2(3) . . ?
C11 C12 C6 124.8(4) . . ?
N1 C6 C5 120.9(3) . . ?
N1 C6 C12 114.7(3) . . ?
C5 C6 C12 124.3(3) . . ?
O2 C11 C12 117.1(3) . . ?
O2 C11 C10 125.6(4) . . ?
C12 C11 C10 117.2(4) . . ?
N1 C2 C3 120.0(4) . . ?
N1 C2 C1 117.4(5) . . ?
C3 C2 C1 122.5(5) . . ?
O1 C5 C4 125.9(4) . . ?
O1 C5 C6 117.8(4) . . ?
C4 C5 C6 116.2(4) . . ?
C9 C10 C11 120.0(4) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
N2 C8 C9 119.9(4) . . ?
N2 C8 C7 117.6(5) . . ?
C9 C8 C7 122.5(4) . . ?
C10 C9 C8 120.4(4) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
O2 C17 C18 106.9(4) . . ?
O2 C17 C16 107.5(5) . . ?
C18 C17 C16 112.8(5) . . ?
O2 C17 H17 109.9 . . ?
C18 C17 H17 109.9 . . ?
C16 C17 H17 109.9 . . ?
C4 C3 C2 119.6(4) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 121.2(5) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C14 C15 C18 117.6(5) . . ?
C14 C15 H15A 107.9 . . ?
C18 C15 H15A 107.9 . . ?
C14 C15 H15B 107.9 . . ?
C18 C15 H15B 107.9 . . ?
H15A C15 H15B 107.2 . . ?
C17 C18 C15 116.9(5) . . ?
C17 C18 H18A 108.1 . . ?
C15 C18 H18A 108.1 . . ?
C17 C18 H18B 108.1 . . ?
C15 C18 H18B 108.1 . . ?
H18A C18 H18B 107.3 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C17 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 C14 C15 107.2(4) . . ?
O1 C14 C13 109.1(5) . . ?
C15 C14 C13 112.2(5) . . ?
O1 C14 H14 109.4 . . ?
C15 C14 H14 109.4 . . ?
C13 C14 H14 109.4 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_refine_diff_density_max         0.311
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.043

