# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_3c
_database_code_depnum_ccdc_archive 'CCDC 1903483'
loop_
_audit_author_name
_audit_author_address
'Alessandra Forni'
;CNR-ISTM
Italy
;
_audit_update_record             
;
2019-03-15 deposited with the CCDC.	2019-06-10 downloaded from the CCDC.
;
#data_lr48

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
{4-methoxy-2-((E)-(3-((E)-2-oxidobenzylideneamino)propylimino)methyl)phenolato}nickel(II)
_chemical_formula_moiety         'C18 H18 N2 Ni O3, C H Cl3'
_chemical_formula_sum            'C19 H19 Cl3 N2 Ni O3'
_chemical_formula_weight         488.42

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'
Ni Ni 0.3393 1.1124 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   10.0155(8)
_cell_length_b                   10.1973(8)
_cell_length_c                   11.2392(11)
_cell_angle_alpha                100.5860(10)
_cell_angle_beta                 97.6650(10)
_cell_angle_gamma                113.6250(10)
_cell_volume                     1006.09(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    5836
_cell_measurement_theta_min      2.259
_cell_measurement_theta_max      31.761

_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    1.386
_shelx_estimated_absorpt_T_min   0.444
_shelx_estimated_absorpt_T_max   0.723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.582
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   
;
SADABS, Bruker, 1997
;
_diffrn_ambient_temperature      291(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 SMART APEX'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_number            21696
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.894
_diffrn_reflns_theta_max         32.569
_diffrn_reflns_theta_full        30.000
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6864
_reflns_number_gt                5915
_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       'SMART (Bruker, 1997)'
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP III ( Burnett&Johnson, 1996)'
_computing_publication_material  SHELXL-2014/7
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0553P)²+0.3248P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6864
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.1069
_refine_ls_wR_factor_gt          0.1015
_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 0.56763(2) 0.58082(2) 0.37271(2) 0.03765(7) Uani 1 1 d . . . . .
O1 O 0.38625(15) 0.56666(14) 0.29392(15) 0.0572(3) Uani 1 1 d . . . . .
O2 O 0.60552(14) 0.77843(13) 0.40206(12) 0.0485(3) Uani 1 1 d . . . . .
O3 O 1.02171(17) 1.28178(15) 0.75096(14) 0.0609(4) Uani 1 1 d . . . . .
N1 N 0.50050(16) 0.37227(15) 0.32706(14) 0.0437(3) Uani 1 1 d . . . . .
N2 N 0.76481(15) 0.63045(15) 0.46248(13) 0.0398(3) Uani 1 1 d . . . . .
C1 C 0.8366(2) 0.5270(2) 0.4577(2) 0.0549(4) Uani 1 1 d . . . . .
H1A H 0.8441 0.5019 0.5366 0.066 Uiso 1 1 calc R U . . .
H1B H 0.9374 0.5776 0.4467 0.066 Uiso 1 1 calc R U . . .
C2 C 0.7536(2) 0.3872(2) 0.35577(19) 0.0520(4) Uani 1 1 d . . . . .
H2A H 0.8061 0.3255 0.3578 0.062 Uiso 1 1 calc R U . . .
H2B H 0.7504 0.4110 0.2760 0.062 Uiso 1 1 calc R U . . .
C3 C 0.5968(2) 0.3035(2) 0.3692(2) 0.0593(5) Uani 1 1 d . . . . .
H3A H 0.5561 0.2014 0.3203 0.071 Uiso 1 1 calc R U . . .
H3B H 0.5982 0.3032 0.4556 0.071 Uiso 1 1 calc R U . . .
C4 C 0.3702(2) 0.27741(18) 0.25752(17) 0.0459(3) Uani 1 1 d . . . . .
H4 H 0.3530 0.1785 0.2391 0.055 Uiso 1 1 calc R U . . .
C5 C 0.25076(18) 0.30670(17) 0.20634(15) 0.0421(3) Uani 1 1 d . . . . .
C6 C 0.1151(2) 0.1871(2) 0.13545(19) 0.0534(4) Uani 1 1 d . . . . .
H6 H 0.1071 0.0911 0.1198 0.064 Uiso 1 1 calc R U . . .
C7 C -0.0047(2) 0.2106(2) 0.0894(2) 0.0599(5) Uani 1 1 d . . . . .
H7 H -0.0940 0.1311 0.0437 0.072 Uiso 1 1 calc R U . . .
C8 C 0.0086(2) 0.3545(3) 0.1118(2) 0.0597(5) Uani 1 1 d . . . . .
H8 H -0.0727 0.3707 0.0807 0.072 Uiso 1 1 calc R U . . .
C9 C 0.1397(2) 0.4732(2) 0.1791(2) 0.0571(5) Uani 1 1 d . . . . .
H9 H 0.1464 0.5686 0.1921 0.069 Uiso 1 1 calc R U . . .
C10 C 0.26399(18) 0.45195(18) 0.22856(16) 0.0445(3) Uani 1 1 d . . . . .
C11 C 0.70887(17) 0.89462(17) 0.48599(15) 0.0385(3) Uani 1 1 d . . . . .
C12 C 0.69693(19) 1.03028(18) 0.50537(17) 0.0462(3) Uani 1 1 d . . . . .
H12 H 0.6170 1.0357 0.4575 0.055 Uiso 1 1 calc R U . . .
C13 C 0.8019(2) 1.15380(19) 0.59394(18) 0.0485(4) Uani 1 1 d . . . . .
H13 H 0.7913 1.2415 0.6062 0.058 Uiso 1 1 calc R U . . .
C14 C 0.92465(19) 1.14999(18) 0.66613(16) 0.0445(3) Uani 1 1 d . . . . .
C15 C 0.94123(18) 1.02080(18) 0.64724(15) 0.0419(3) Uani 1 1 d . . . . .
H15 H 1.0240 1.0181 0.6933 0.050 Uiso 1 1 calc R U . . .
C16 C 0.83218(16) 0.89180(17) 0.55772(14) 0.0372(3) Uani 1 1 d . . . . .
C17 C 0.85476(17) 0.76052(18) 0.53575(15) 0.0406(3) Uani 1 1 d . . . . .
H17 H 0.9449 0.7691 0.5792 0.049 Uiso 1 1 calc R U . . .
C18 C 1.1503(2) 1.2845(3) 0.8237(2) 0.0626(5) Uani 1 1 d . . . . .
H18A H 1.1200 1.2085 0.8673 0.094 Uiso 1 1 calc R U . . .
H18B H 1.2058 1.3795 0.8827 0.094 Uiso 1 1 calc R U . . .
H18C H 1.2123 1.2672 0.7705 0.094 Uiso 1 1 calc R U . . .
C19 C 0.4981(2) 0.8203(2) 0.14499(19) 0.0566(4) Uani 1 1 d . . . . .
H19 H 0.5035 0.7810 0.2179 0.068 Uiso 1 1 calc R U . . .
Cl1 Cl 0.66616(8) 0.97861(9) 0.16620(8) 0.0883(2) Uani 1 1 d . . . . .
Cl2 Cl 0.34800(9) 0.86792(10) 0.13482(9) 0.0961(2) Uani 1 1 d . . . . .
Cl3 Cl 0.47398(13) 0.68479(12) 0.01466(9) 0.1211(4) 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 1.8489(12) . ?
Ni1 O2 1.8501(11) . ?
Ni1 N1 1.8971(14) . ?
Ni1 N2 1.9115(13) . ?
O1 C10 1.305(2) . ?
O2 C11 1.3081(19) . ?
O3 C14 1.377(2) . ?
O3 C18 1.418(3) . ?
N1 C4 1.299(2) . ?
N1 C3 1.480(2) . ?
N2 C17 1.301(2) . ?
N2 C1 1.493(2) . ?
C1 C2 1.494(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.502(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.420(2) . ?
C4 H4 0.9300 . ?
C5 C10 1.404(2) . ?
C5 C6 1.412(2) . ?
C6 C7 1.369(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.391(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.373(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.408(2) . ?
C9 H9 0.9300 . ?
C11 C16 1.396(2) . ?
C11 C12 1.416(2) . ?
C12 C13 1.372(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.398(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.375(2) . ?
C15 C16 1.416(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.428(2) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 Cl3 1.734(2) . ?
C19 Cl1 1.752(2) . ?
C19 Cl2 1.752(2) . ?
C19 H19 0.9800 . ?

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 78.57(5) . . ?
O1 Ni1 N1 92.74(6) . . ?
O2 Ni1 N1 171.26(6) . . ?
O1 Ni1 N2 170.36(6) . . ?
O2 Ni1 N2 91.81(5) . . ?
N1 Ni1 N2 96.89(6) . . ?
C10 O1 Ni1 131.18(11) . . ?
C11 O2 Ni1 130.17(10) . . ?
C14 O3 C18 117.05(16) . . ?
C4 N1 C3 113.85(15) . . ?
C4 N1 Ni1 124.79(12) . . ?
C3 N1 Ni1 121.36(12) . . ?
C17 N2 C1 111.03(14) . . ?
C17 N2 Ni1 123.94(10) . . ?
C1 N2 Ni1 125.03(12) . . ?
N2 C1 C2 113.69(15) . . ?
N2 C1 H1A 108.8 . . ?
C2 C1 H1A 108.8 . . ?
N2 C1 H1B 108.8 . . ?
C2 C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?
C1 C2 C3 111.01(17) . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
N1 C3 C2 110.58(15) . . ?
N1 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
N1 C4 C5 127.78(15) . . ?
N1 C4 H4 116.1 . . ?
C5 C4 H4 116.1 . . ?
C10 C5 C6 119.69(16) . . ?
C10 C5 C4 121.01(15) . . ?
C6 C5 C4 119.27(16) . . ?
C7 C6 C5 120.88(18) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 119.33(18) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C9 C8 C7 121.12(19) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 120.67(19) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
O1 C10 C5 122.39(15) . . ?
O1 C10 C9 119.30(16) . . ?
C5 C10 C9 118.31(16) . . ?
O2 C11 C16 122.96(14) . . ?
O2 C11 C12 119.13(14) . . ?
C16 C11 C12 117.91(14) . . ?
C13 C12 C11 120.75(15) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 121.06(15) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C15 C14 O3 125.47(16) . . ?
C15 C14 C13 119.49(15) . . ?
O3 C14 C13 115.03(15) . . ?
C14 C15 C16 119.98(15) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C11 C16 C15 120.78(14) . . ?
C11 C16 C17 120.02(14) . . ?
C15 C16 C17 119.08(14) . . ?
N2 C17 C16 128.03(14) . . ?
N2 C17 H17 116.0 . . ?
C16 C17 H17 116.0 . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
Cl3 C19 Cl1 110.57(13) . . ?
Cl3 C19 Cl2 111.65(12) . . ?
Cl1 C19 Cl2 109.83(12) . . ?
Cl3 C19 H19 108.2 . . ?
Cl1 C19 H19 108.2 . . ?
Cl2 C19 H19 108.2 . . ?

_refine_diff_density_max         0.550
_refine_diff_density_min         -0.612
_refine_diff_density_rms         0.052

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: isopropyl ether/chloroform'
####################################################################### 
# 
# 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_3j
_database_code_depnum_ccdc_archive 'CCDC 1903485'
loop_
_audit_author_name
_audit_author_address
'Alessandra Forni'
;CNR-ISTM
Italy
;
_audit_update_record             
;
2019-03-15 deposited with the CCDC.	2019-06-10 downloaded from the CCDC.
;
#data_lr38

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
{4-nitro-2-((E)-(3-((E)-2-oxidobenzylideneamino)propylimino)methyl)phenolato}nickel(II)
_chemical_formula_moiety         'C17 H15 N3 Ni O4'
_chemical_formula_sum            'C17 H15 N3 Ni O4'
_chemical_formula_weight         384.03

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'
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                   10.9731(6)
_cell_length_b                   10.7934(6)
_cell_length_c                   13.7310(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.6060(10)
_cell_angle_gamma                90
_cell_volume                     1618.48(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6997
_cell_measurement_theta_min      2.271
_cell_measurement_theta_max      30.979

_exptl_crystal_description       'rectangular prism'
_exptl_crystal_colour            red
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.227
_shelx_estimated_absorpt_T_min   0.673
_shelx_estimated_absorpt_T_max   0.791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.644
_exptl_absorpt_correction_T_max  0.746

_exptl_absorpt_process_details   
;
SADABS, Bruker, 1997
;
_diffrn_ambient_temperature      293(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 SMART APEX'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_number            30966
_diffrn_reflns_av_unetI/netI     0.0120
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.865
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_full        29.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4717
_reflns_number_gt                4090
_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       'SMART (Bruker, 1997)'
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP III ( Burnett&Johnson, 1996)'
_computing_publication_material  SHELXL-2014/7
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0374P)²+0.4111P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4717
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0255
_refine_ls_wR_factor_ref         0.0729
_refine_ls_wR_factor_gt          0.0680
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 0.43540(2) 0.02752(2) 0.10820(2) 0.03329(6) Uani 1 1 d . . . . .
O1 O 0.59018(8) 0.06664(9) 0.16716(7) 0.0394(2) Uani 1 1 d . . . . .
O2 O 0.45050(9) 0.17507(9) 0.04268(8) 0.0469(2) Uani 1 1 d . . . . .
O3 O 0.92074(12) -0.37042(12) 0.33052(10) 0.0660(3) Uani 1 1 d . . . . .
O4 O 1.05110(11) -0.21973(14) 0.33796(12) 0.0756(4) Uani 1 1 d . . . . .
N1 N 0.42235(10) -0.10948(10) 0.19058(8) 0.0374(2) Uani 1 1 d . . . . .
N2 N 0.28435(10) -0.00851(12) 0.03921(8) 0.0403(2) Uani 1 1 d . . . . .
N3 N 0.94658(12) -0.26071(13) 0.31912(10) 0.0511(3) Uani 1 1 d . . . . .
C1 C 0.25158(15) -0.14053(16) 0.02779(12) 0.0528(4) Uani 1 1 d . . . . .
H1A H 0.3185 -0.1847 0.0021 0.063 Uiso 1 1 calc R U . . .
H1B H 0.1801 -0.1483 -0.0193 0.063 Uiso 1 1 calc R U . . .
C2 C 0.22454(18) -0.1997(2) 0.12363(13) 0.0693(5) Uani 1 1 d . . . . .
H2A H 0.1380 -0.1902 0.1310 0.083 Uiso 1 1 calc R U . . .
H2B H 0.2417 -0.2877 0.1209 0.083 Uiso 1 1 calc R U . . .
C3 C 0.29761(13) -0.14527(16) 0.21232(11) 0.0492(3) Uani 1 1 d . . . . .
H3A H 0.2554 -0.0729 0.2342 0.059 Uiso 1 1 calc R U . . .
H3B H 0.3034 -0.2056 0.2649 0.059 Uiso 1 1 calc R U . . .
C4 C 0.51249(12) -0.17006(12) 0.23434(10) 0.0397(3) Uani 1 1 d . . . . .
H4 H 0.4949 -0.2412 0.2685 0.048 Uiso 1 1 calc R U . . .
C5 C 0.63907(11) -0.13469(12) 0.23386(9) 0.0353(2) Uani 1 1 d . . . . .
C6 C 0.73112(12) -0.21583(12) 0.27115(9) 0.0394(3) Uani 1 1 d . . . . .
H6 H 0.7115 -0.2962 0.2884 0.047 Uiso 1 1 calc R U . . .
C7 C 0.85089(12) -0.17652(13) 0.28227(9) 0.0396(3) Uani 1 1 d . . . . .
C8 C 0.88290(12) -0.05552(14) 0.26016(10) 0.0406(3) Uani 1 1 d . . . . .
H8 H 0.9640 -0.0298 0.2703 0.049 Uiso 1 1 calc R U . . .
C9 C 0.79383(12) 0.02512(12) 0.22339(10) 0.0388(3) Uani 1 1 d . . . . .
H9 H 0.8151 0.1061 0.2092 0.047 Uiso 1 1 calc R U . . .
C10 C 0.66981(11) -0.01233(11) 0.20644(9) 0.0333(2) Uani 1 1 d . . . . .
C11 C 0.35856(14) 0.24507(14) 0.00795(10) 0.0453(3) Uani 1 1 d . . . . .
C12 C 0.38140(19) 0.36999(17) -0.01210(16) 0.0680(5) Uani 1 1 d . . . . .
H12 H 0.4612 0.3999 -0.0036 0.082 Uiso 1 1 calc R U . . .
C13 C 0.2871(3) 0.4492(2) -0.04430(18) 0.0839(7) Uani 1 1 d . . . . .
H13 H 0.3043 0.5319 -0.0561 0.101 Uiso 1 1 calc R U . . .
C14 C 0.1679(2) 0.4078(2) -0.05928(15) 0.0789(6) Uani 1 1 d . . . . .
H14 H 0.1048 0.4624 -0.0792 0.095 Uiso 1 1 calc R U . . .
C15 C 0.14395(17) 0.2859(2) -0.04454(12) 0.0628(5) Uani 1 1 d . . . . .
H15 H 0.0641 0.2571 -0.0573 0.075 Uiso 1 1 calc R U . . .
C16 C 0.23728(13) 0.20238(15) -0.01041(10) 0.0453(3) Uani 1 1 d . . . . .
C17 C 0.21072(12) 0.07318(16) -0.00205(10) 0.0450(3) Uani 1 1 d . . . . .
H17 H 0.1341 0.0460 -0.0285 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 O2 1.8446(10) . ?
Ni1 O1 1.8573(9) . ?
Ni1 N2 1.8679(11) . ?
Ni1 N1 1.8757(11) . ?
O1 C10 1.2996(15) . ?
O2 C11 1.3122(17) . ?
O3 N3 1.2312(19) . ?
O4 N3 1.2328(19) . ?
N1 C4 1.2849(17) . ?
N1 C3 1.4805(17) . ?
N2 C17 1.289(2) . ?
N2 C1 1.474(2) . ?
N3 C7 1.4424(17) . ?
C1 C2 1.518(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.510(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.4411(18) . ?
C4 H4 0.9300 . ?
C5 C6 1.3958(17) . ?
C5 C10 1.4228(17) . ?
C6 C7 1.3753(19) . ?
C6 H6 0.9300 . ?
C7 C8 1.394(2) . ?
C8 C9 1.3680(19) . ?
C8 H8 0.9300 . ?
C9 C10 1.4169(18) . ?
C9 H9 0.9300 . ?
C11 C12 1.404(2) . ?
C11 C16 1.408(2) . ?
C12 C13 1.381(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.378(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.361(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.410(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.432(2) . ?
C17 H17 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
O2 Ni1 O1 83.94(4) . . ?
O2 Ni1 N2 92.86(5) . . ?
O1 Ni1 N2 175.36(5) . . ?
O2 Ni1 N1 172.13(5) . . ?
O1 Ni1 N1 92.11(4) . . ?
N2 Ni1 N1 91.46(5) . . ?
C10 O1 Ni1 125.51(8) . . ?
C11 O2 Ni1 124.88(9) . . ?
C4 N1 C3 117.24(12) . . ?
C4 N1 Ni1 125.63(9) . . ?
C3 N1 Ni1 116.99(9) . . ?
C17 N2 C1 118.59(13) . . ?
C17 N2 Ni1 124.57(11) . . ?
C1 N2 Ni1 116.76(10) . . ?
O3 N3 O4 122.65(14) . . ?
O3 N3 C7 118.80(14) . . ?
O4 N3 C7 118.55(14) . . ?
N2 C1 C2 112.36(14) . . ?
N2 C1 H1A 109.1 . . ?
C2 C1 H1A 109.1 . . ?
N2 C1 H1B 109.1 . . ?
C2 C1 H1B 109.1 . . ?
H1A C1 H1B 107.9 . . ?
C3 C2 C1 113.73(13) . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
C1 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
N1 C3 C2 111.56(13) . . ?
N1 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
N1 C3 H3B 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
N1 C4 C5 124.15(12) . . ?
N1 C4 H4 117.9 . . ?
C5 C4 H4 117.9 . . ?
C6 C5 C10 119.85(12) . . ?
C6 C5 C4 119.69(12) . . ?
C10 C5 C4 120.04(11) . . ?
C7 C6 C5 119.78(12) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 121.56(12) . . ?
C6 C7 N3 119.98(13) . . ?
C8 C7 N3 118.46(13) . . ?
C9 C8 C7 119.37(13) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 121.28(12) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
O1 C10 C9 118.49(11) . . ?
O1 C10 C5 123.47(11) . . ?
C9 C10 C5 118.04(11) . . ?
O2 C11 C12 118.60(15) . . ?
O2 C11 C16 123.81(14) . . ?
C12 C11 C16 117.59(15) . . ?
C13 C12 C11 121.0(2) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C12 121.2(2) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C15 C14 C13 119.06(18) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C14 C15 C16 121.54(19) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C11 C16 C15 119.57(16) . . ?
C11 C16 C17 120.06(13) . . ?
C15 C16 C17 120.18(15) . . ?
N2 C17 C16 125.29(13) . . ?
N2 C17 H17 117.4 . . ?
C16 C17 H17 117.4 . . ?

_refine_diff_density_max         0.356
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.046


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: isopropyl ether/chloroform'
####################################################################### 
# 
# 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_3g
_database_code_depnum_ccdc_archive 'CCDC 1903484'
loop_
_audit_author_name
_audit_author_address
'Alessandra Forni'
;CNR-ISTM
Italy
;
_audit_update_record             
;
2019-03-15 deposited with the CCDC.	2019-06-10 downloaded from the CCDC.
;
#data_lr47

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'{4-bromo-2-((E)-(3-((E)-5-methoxy-2-oxidobenzylideneamino)propylimino)methyl)phenolato}nickel(II) ethanol monosolvate'
_chemical_formula_moiety         'C18 H17 Br N2 Ni O3, C2 H6 O'
_chemical_formula_sum            'C20 H23 Br N2 Ni O4'
_chemical_formula_weight         494.02

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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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                   10.5470(11)
_cell_length_b                   9.3472(10)
_cell_length_c                   20.660(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.9680(10)
_cell_angle_gamma                90
_cell_volume                     2011.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    4058
_cell_measurement_theta_min      2.397
_cell_measurement_theta_max      20.382

_exptl_crystal_description       plate
_exptl_crystal_colour            brown
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    2.979
_shelx_estimated_absorpt_T_min   0.479
_shelx_estimated_absorpt_T_max   0.916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.584
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   
;
SADABS, Bruker, 1997
;
_diffrn_ambient_temperature      291(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 SMART APEX'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_number            28896
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.955
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4614
_reflns_number_gt                2787
_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       'SMART (Bruker, 1997)'
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP III ( Burnett&Johnson, 1996)'
_computing_publication_material  SHELXL-2014/7
_refine_special_details          
; 
 The cocrystallized ethanol molecule is characterized by large disorder.
 One restraint (DFIX) was applied to the C-C distance of this molecule. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0816P)²+1.5345P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4614
_refine_ls_number_parameters     273
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1016
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1709
_refine_ls_wR_factor_gt          0.1443
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.043
_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
Ni Ni 0.04880(5) 0.85777(6) 0.04723(3) 0.0496(2) Uani 1 1 d . . . . .
Br Br 0.47942(8) 1.36285(8) 0.25052(4) 0.1125(3) Uani 1 1 d . . . . .
O1 O 0.2140(3) 0.9328(4) 0.06009(16) 0.0672(9) Uani 1 1 d . . . . .
O2 O 0.1218(3) 0.7609(3) -0.01615(15) 0.0619(8) Uani 1 1 d . . . . .
O3 O -0.0639(4) 0.3770(4) -0.20976(17) 0.0719(10) Uani 1 1 d . . . . .
N1 N -0.0008(4) 0.9742(5) 0.1148(2) 0.0667(11) Uani 1 1 d . . . . .
N2 N -0.1105(3) 0.7591(4) 0.02543(18) 0.0558(9) Uani 1 1 d . . . . .
C1 C -0.2227(5) 0.7804(7) 0.0592(3) 0.0818(16) Uani 1 1 d . . . . .
H1A H -0.2634 0.6883 0.0630 0.098 Uiso 0.7 1 calc R U P A 1
H1B H -0.2840 0.8409 0.0320 0.098 Uiso 0.7 1 calc R U P A 1
H1C H -0.3002 0.7616 0.0285 0.098 Uiso 0.3 1 calc R U P B 2
H1D H -0.2188 0.7113 0.0945 0.098 Uiso 0.3 1 calc R U P B 2
C2A C -0.1941(8) 0.8457(9) 0.1259(4) 0.073(2) Uani 0.7 1 d . . P C 1
H2A1 H -0.2725 0.8520 0.1448 0.087 Uiso 0.7 1 calc R U P C 1
H2A2 H -0.1340 0.7856 0.1540 0.087 Uiso 0.7 1 calc R U P C 1
C3A C -0.1398(12) 0.9876(12) 0.1220(6) 0.075(3) Uani 0.7 1 d . . P C 1
H3A1 H -0.1477 1.0412 0.1613 0.090 Uiso 0.7 1 calc R U P C 1
H3A2 H -0.1860 1.0386 0.0847 0.090 Uiso 0.7 1 calc R U P C 1
C2B C -0.2308(12) 0.9255(18) 0.0865(7) 0.047(3) Uani 0.3 1 d . . P C 2
H2B1 H -0.3130 0.9403 0.1011 0.057 Uiso 0.3 1 calc R U P C 2
H2B2 H -0.2196 0.9979 0.0542 0.057 Uiso 0.3 1 calc R U P C 2
C3B C -0.116(2) 0.931(3) 0.1470(12) 0.070(7) Uani 0.3 1 d . . P C 2
H3B1 H -0.1326 1.0005 0.1793 0.084 Uiso 0.3 1 calc R U P C 2
H3B2 H -0.1025 0.8376 0.1679 0.084 Uiso 0.3 1 calc R U P C 2
C4 C 0.0755(5) 1.0617(6) 0.1513(2) 0.0638(12) Uani 1 1 d . . . . .
H4 H 0.0392 1.1117 0.1828 0.077 Uiso 1 1 calc R U . . .
C5 C 0.2060(5) 1.0900(5) 0.1493(2) 0.0557(11) Uani 1 1 d . . . . .
C6 C 0.2698(5) 1.1907(5) 0.1937(2) 0.0679(13) Uani 1 1 d . . . . .
H6 H 0.2273 1.2325 0.2251 0.082 Uiso 1 1 calc R U . . .
C7 C 0.3934(6) 1.2265(5) 0.1905(3) 0.0723(14) Uani 1 1 d . . . . .
C8 C 0.4555(5) 1.1672(5) 0.1430(3) 0.0737(14) Uani 1 1 d . . . . .
H8 H 0.5394 1.1946 0.1406 0.088 Uiso 1 1 calc R U . . .
C9 C 0.3967(5) 1.0696(6) 0.0998(3) 0.0709(13) Uani 1 1 d . . . . .
H9 H 0.4409 1.0305 0.0685 0.085 Uiso 1 1 calc R U . . .
C10 C 0.2690(4) 1.0270(5) 0.1021(2) 0.0562(11) Uani 1 1 d . . . . .
C11 C 0.0707(4) 0.6714(4) -0.0621(2) 0.0526(10) Uani 1 1 d . . . . .
C12 C 0.1452(5) 0.6257(5) -0.1092(2) 0.0629(12) Uani 1 1 d . . . . .
H12 H 0.2283 0.6601 -0.1079 0.076 Uiso 1 1 calc R U . . .
C13 C 0.0952(5) 0.5303(5) -0.1568(2) 0.0637(12) Uani 1 1 d . . . . .
H13 H 0.1451 0.5014 -0.1878 0.076 Uiso 1 1 calc R U . . .
C14 C -0.0273(5) 0.4762(5) -0.1599(2) 0.0577(11) Uani 1 1 d . . . . .
C15 C -0.1013(5) 0.5184(5) -0.1148(2) 0.0572(11) Uani 1 1 d . . . . .
H15 H -0.1839 0.4822 -0.1166 0.069 Uiso 1 1 calc R U . . .
C16 C -0.0523(4) 0.6176(4) -0.0648(2) 0.0496(10) Uani 1 1 d . . . . .
C17 C -0.1329(4) 0.6649(5) -0.0212(2) 0.0561(11) Uani 1 1 d . . . . .
H17 H -0.2137 0.6229 -0.0264 0.067 Uiso 1 1 calc R U . . .
C18 C -0.1857(6) 0.3186(5) -0.2138(2) 0.0723(14) Uani 1 1 d . . . . .
H18A H -0.1942 0.2734 -0.1730 0.108 Uiso 1 1 calc R U . . .
H18B H -0.1985 0.2490 -0.2483 0.108 Uiso 1 1 calc R U . . .
H18C H -0.2487 0.3930 -0.2228 0.108 Uiso 1 1 calc R U . . .
O1E O 0.4053(9) 0.7731(14) -0.0024(6) 0.252(5) Uani 1 1 d . . . . .
H1E H 0.3577 0.8332 0.0099 0.379 Uiso 1 1 calc R U . . .
C1E C 0.3921(18) 0.6376(11) 0.0318(9) 0.277(11) Uani 1 1 d D . . . .
H1E1 H 0.3032 0.6258 0.0375 0.333 Uiso 1 1 calc R U . . .
H1E2 H 0.4137 0.5595 0.0046 0.333 Uiso 1 1 calc R U . . .
C2E C 0.4689(12) 0.6288(17) 0.0925(5) 0.269(10) Uani 1 1 d D . . . .
H2E1 H 0.4157 0.6249 0.1262 0.404 Uiso 1 1 calc R U . . .
H2E2 H 0.5235 0.7114 0.0991 0.404 Uiso 1 1 calc R U . . .
H2E3 H 0.5207 0.5440 0.0944 0.404 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 O2 1.855(3) . ?
Ni O1 1.859(3) . ?
Ni N1 1.906(4) . ?
Ni N2 1.908(4) . ?
Br C7 1.907(5) . ?
O1 C10 1.307(5) . ?
O2 C11 1.317(5) . ?
O3 C18 1.386(6) . ?
O3 C14 1.395(5) . ?
N1 C4 1.303(6) . ?
N1 C3A 1.501(12) . ?
N1 C3B 1.53(3) . ?
N2 C17 1.299(5) . ?
N2 C1 1.478(6) . ?
C1 C2B 1.477(17) . ?
C1 C2A 1.493(10) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C2A C3A 1.452(14) . ?
C2A H2A1 0.9700 . ?
C2A H2A2 0.9700 . ?
C3A H3A1 0.9700 . ?
C3A H3A2 0.9700 . ?
C2B C3B 1.60(3) . ?
C2B H2B1 0.9700 . ?
C2B H2B2 0.9700 . ?
C3B H3B1 0.9700 . ?
C3B H3B2 0.9700 . ?
C4 C5 1.409(7) . ?
C4 H4 0.9300 . ?
C5 C10 1.394(6) . ?
C5 C6 1.409(7) . ?
C6 C7 1.357(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.378(8) . ?
C8 C9 1.357(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.412(7) . ?
C9 H9 0.9300 . ?
C11 C16 1.384(6) . ?
C11 C12 1.409(6) . ?
C12 C13 1.371(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.380(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.364(6) . ?
C15 C16 1.423(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.404(6) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
O1E C1E 1.467(15) . ?
O1E H1E 0.8200 . ?
C1E C2E 1.386(14) . ?
C1E H1E1 0.9700 . ?
C1E H1E2 0.9700 . ?
C2E H2E1 0.9600 . ?
C2E H2E2 0.9600 . ?
C2E H2E3 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
O2 Ni O1 78.59(13) . . ?
O2 Ni N1 170.73(16) . . ?
O1 Ni N1 92.19(16) . . ?
O2 Ni N2 92.55(14) . . ?
O1 Ni N2 170.97(15) . . ?
N1 Ni N2 96.69(16) . . ?
C10 O1 Ni 131.2(3) . . ?
C11 O2 Ni 130.6(3) . . ?
C18 O3 C14 117.0(4) . . ?
C4 N1 C3A 114.5(6) . . ?
C4 N1 C3B 112.1(10) . . ?
C4 N1 Ni 124.6(3) . . ?
C3A N1 Ni 120.3(6) . . ?
C3B N1 Ni 119.6(11) . . ?
C17 N2 C1 112.0(4) . . ?
C17 N2 Ni 123.6(3) . . ?
C1 N2 Ni 124.3(3) . . ?
C2B C1 N2 113.7(7) . . ?
N2 C1 C2A 115.4(5) . . ?
N2 C1 H1A 108.4 . . ?
C2A C1 H1A 108.4 . . ?
N2 C1 H1B 108.4 . . ?
C2A C1 H1B 108.4 . . ?
H1A C1 H1B 107.5 . . ?
C2B C1 H1C 108.8 . . ?
N2 C1 H1C 108.8 . . ?
C2B C1 H1D 108.8 . . ?
N2 C1 H1D 108.8 . . ?
H1C C1 H1D 107.7 . . ?
C3A C2A C1 110.3(8) . . ?
C3A C2A H2A1 109.6 . . ?
C1 C2A H2A1 109.6 . . ?
C3A C2A H2A2 109.6 . . ?
C1 C2A H2A2 109.6 . . ?
H2A1 C2A H2A2 108.1 . . ?
C2A C3A N1 109.2(8) . . ?
C2A C3A H3A1 109.8 . . ?
N1 C3A H3A1 109.8 . . ?
C2A C3A H3A2 109.8 . . ?
N1 C3A H3A2 109.8 . . ?
H3A1 C3A H3A2 108.3 . . ?
C1 C2B C3B 104.1(14) . . ?
C1 C2B H2B1 110.9 . . ?
C3B C2B H2B1 110.9 . . ?
C1 C2B H2B2 110.9 . . ?
C3B C2B H2B2 110.9 . . ?
H2B1 C2B H2B2 109.0 . . ?
N1 C3B C2B 102.9(16) . . ?
N1 C3B H3B1 111.2 . . ?
C2B C3B H3B1 111.2 . . ?
N1 C3B H3B2 111.2 . . ?
C2B C3B H3B2 111.2 . . ?
H3B1 C3B H3B2 109.1 . . ?
N1 C4 C5 128.3(4) . . ?
N1 C4 H4 115.9 . . ?
C5 C4 H4 115.9 . . ?
C10 C5 C4 121.0(4) . . ?
C10 C5 C6 120.4(5) . . ?
C4 C5 C6 118.4(4) . . ?
C7 C6 C5 119.8(5) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 120.2(5) . . ?
C6 C7 Br 119.8(4) . . ?
C8 C7 Br 120.0(4) . . ?
C9 C8 C7 121.3(5) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 120.6(5) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
O1 C10 C5 122.6(4) . . ?
O1 C10 C9 119.7(4) . . ?
C5 C10 C9 117.7(4) . . ?
O2 C11 C16 122.4(4) . . ?
O2 C11 C12 118.7(4) . . ?
C16 C11 C12 118.8(4) . . ?
C13 C12 C11 119.9(5) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 121.6(4) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C15 C14 C13 119.6(4) . . ?
C15 C14 O3 125.0(4) . . ?
C13 C14 O3 115.3(4) . . ?
C14 C15 C16 120.1(4) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C11 C16 C17 121.1(4) . . ?
C11 C16 C15 119.9(4) . . ?
C17 C16 C15 118.9(4) . . ?
N2 C17 C16 129.2(4) . . ?
N2 C17 H17 115.4 . . ?
C16 C17 H17 115.4 . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C1E O1E H1E 109.5 . . ?
C2E C1E O1E 113.6(14) . . ?
C2E C1E H1E1 108.8 . . ?
O1E C1E H1E1 108.8 . . ?
C2E C1E H1E2 108.8 . . ?
O1E C1E H1E2 108.8 . . ?
H1E1 C1E H1E2 107.7 . . ?
C1E C2E H2E1 109.5 . . ?
C1E C2E H2E2 109.5 . . ?
H2E1 C2E H2E2 109.5 . . ?
C1E C2E H2E3 109.5 . . ?
H2E1 C2E H2E3 109.5 . . ?
H2E2 C2E H2E3 109.5 . . ?

_refine_diff_density_max         0.769
_refine_diff_density_min         -0.905
_refine_diff_density_rms         0.076

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-hexane/ethanol'
