# 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_compound1
_database_code_depnum_ccdc_archive 'CCDC 1893175'
loop_
_audit_author_name
_audit_author_address
'Stephane BAUDRON'
;University of Strasbourg
France
;
_audit_update_record             
;
2019-01-24 deposited with the CCDC.	2019-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C64 H40 N8 O4 Zn2'
_chemical_formula_weight         1115.78

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'
Zn Zn 0.2839 1.4301 '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      tetragonal
_space_group_IT_number           118
_space_group_name_H-M_alt        'P -4 n 2'
_space_group_name_Hall           'P -4 -2n'

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

_cell_length_a                   11.9527(3)
_cell_length_b                   11.9527(3)
_cell_length_c                   17.7035(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2529.25(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9969
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      23.52

_exptl_crystal_description       rod
_exptl_crystal_colour            dark-green
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_F_000             1144
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    1.010
_shelx_estimated_absorpt_T_min   0.906
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.905
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(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            40519
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.056
_diffrn_reflns_theta_max         30.193
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3750
_reflns_number_gt                2709
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.832
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    1.000

_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.0758P)²+1.2543P] 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 1015 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3750
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1443
_refine_ls_wR_factor_gt          0.1285
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
C1 C 0.7238(5) 0.9632(5) 0.5855(3) 0.0494(13) Uani 1 1 d . . . . .
H1 H 0.711223 0.885461 0.578301 0.059 Uiso 1 1 calc R U . . .
C2 C 0.8260(5) 1.0161(5) 0.5724(4) 0.0551(15) Uani 1 1 d . . . . .
H2 H 0.893197 0.981561 0.555754 0.066 Uiso 1 1 calc R U . . .
C3 C 0.8107(5) 1.1284(5) 0.5882(3) 0.0491(13) Uani 1 1 d . . . . .
H3 H 0.864637 1.186286 0.583408 0.059 Uiso 1 1 calc R U . . .
C4 C 0.6978(4) 1.1399(4) 0.6131(3) 0.0395(10) Uani 1 1 d . . . . .
C5 C 0.6453(4) 1.2368(4) 0.6391(3) 0.0382(10) Uani 1 1 d . . . . .
C6 C 0.5432(5) 1.2428(4) 0.6761(3) 0.0423(11) Uani 1 1 d . . . . .
C7 C 0.4795(6) 1.3411(5) 0.6941(6) 0.075(2) Uani 1 1 d . . . . .
H7 H 0.499685 1.416225 0.683169 0.090 Uiso 1 1 calc R U . . .
C8 C 0.3847(6) 1.3062(5) 0.7296(5) 0.077(2) Uani 1 1 d . . . . .
H8 H 0.326681 1.352736 0.748604 0.093 Uiso 1 1 calc R U . . .
C9 C 0.3882(4) 1.1906(4) 0.7331(3) 0.0452(12) Uani 1 1 d . . . . .
C10 C 0.7081(4) 1.3430(4) 0.6269(3) 0.0401(10) Uani 1 1 d . . . . .
C11 C 0.7349(6) 1.3793(5) 0.5544(3) 0.0547(15) Uani 1 1 d . . . . .
H11 H 0.708742 1.338747 0.511794 0.066 Uiso 1 1 calc R U . . .
C12 C 0.7996(6) 1.4745(5) 0.5442(3) 0.0566(16) Uani 1 1 d . . . . .
H12 H 0.818617 1.497911 0.494528 0.068 Uiso 1 1 calc R U . . .
C13 C 0.8363(5) 1.5347(4) 0.6050(3) 0.0450(11) Uani 1 1 d . . . . .
C14 C 0.8108(6) 1.4997(4) 0.6769(3) 0.0498(13) Uani 1 1 d . . . . .
H14 H 0.838114 1.540178 0.719217 0.060 Uiso 1 1 calc R U . . .
C15 C 0.7449(5) 1.4050(4) 0.6878(3) 0.0476(12) Uani 1 1 d . . . . .
H15 H 0.725129 1.382910 0.737633 0.057 Uiso 1 1 calc R U . . .
C16 C 0.9043(5) 1.6371(5) 0.5933(3) 0.0542(14) Uani 1 1 d . . . . .
H16 H 0.919978 1.657196 0.542456 0.065 Uiso 1 1 calc R U . . .
N1 N 0.4813(3) 1.1515(3) 0.6999(2) 0.0353(8) Uani 1 1 d . . . . .
N2 N 0.6457(4) 1.0351(4) 0.6094(2) 0.0394(9) Uani 1 1 d . . . . .
Zn1 Zn 0.500000 1.000000 0.65735(4) 0.0346(2) Uani 1 2 d S T P . .
O1 O 0.9408(5) 1.6961(4) 0.6407(3) 0.0756(14) 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
C1 N2 1.338(7) . ?
C1 C2 1.394(8) . ?
C1 H1 0.9500 . ?
C2 C3 1.383(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.426(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(7) . ?
C4 N2 1.400(6) . ?
C5 C6 1.387(7) . ?
C5 C10 1.490(6) . ?
C6 N1 1.385(6) . ?
C6 C7 1.435(8) . ?
C7 C8 1.362(9) . ?
C7 H7 0.9500 . ?
C8 C9 1.384(7) . ?
C8 H8 0.9500 . ?
C9 N1 1.343(6) . ?
C9 C9 1.460(10) 8_666 ?
C10 C15 1.381(7) . ?
C10 C11 1.392(7) . ?
C11 C12 1.387(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.368(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.374(8) . ?
C13 C16 1.483(8) . ?
C14 C15 1.392(7) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 O1 1.180(7) . ?
C16 H16 0.9500 . ?
N1 Zn1 1.973(4) . ?
N2 Zn1 1.982(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 C2 111.9(5) . . ?
N2 C1 H1 124.1 . . ?
C2 C1 H1 124.1 . . ?
C3 C2 C1 106.9(5) . . ?
C3 C2 H2 126.6 . . ?
C1 C2 H2 126.6 . . ?
C2 C3 C4 106.3(5) . . ?
C2 C3 H3 126.8 . . ?
C4 C3 H3 126.8 . . ?
C5 C4 N2 123.9(4) . . ?
C5 C4 C3 127.5(4) . . ?
N2 C4 C3 108.7(4) . . ?
C6 C5 C4 126.5(4) . . ?
C6 C5 C10 117.8(4) . . ?
C4 C5 C10 115.6(4) . . ?
N1 C6 C5 124.9(5) . . ?
N1 C6 C7 107.1(5) . . ?
C5 C6 C7 127.9(5) . . ?
C8 C7 C6 107.1(5) . . ?
C8 C7 H7 126.5 . . ?
C6 C7 H7 126.5 . . ?
C7 C8 C9 107.5(5) . . ?
C7 C8 H8 126.3 . . ?
C9 C8 H8 126.3 . . ?
N1 C9 C8 110.7(4) . . ?
N1 C9 C9 119.3(3) . 8_666 ?
C8 C9 C9 130.0(4) . 8_666 ?
C15 C10 C11 118.6(4) . . ?
C15 C10 C5 120.4(4) . . ?
C11 C10 C5 120.9(4) . . ?
C12 C11 C10 120.3(5) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 120.5(5) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 119.8(5) . . ?
C12 C13 C16 120.0(5) . . ?
C14 C13 C16 120.2(5) . . ?
C13 C14 C15 120.2(5) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 120.5(5) . . ?
C10 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
O1 C16 C13 126.5(5) . . ?
O1 C16 H16 116.7 . . ?
C13 C16 H16 116.7 . . ?
C9 N1 C6 107.5(4) . . ?
C9 N1 Zn1 125.5(3) . . ?
C6 N1 Zn1 123.2(3) . . ?
C1 N2 C4 106.2(4) . . ?
C1 N2 Zn1 127.8(4) . . ?
C4 N2 Zn1 124.1(3) . . ?
N1 Zn1 N1 135.1(2) 2_675 . ?
N1 Zn1 N2 93.94(16) 2_675 2_675 ?
N1 Zn1 N2 104.93(16) . 2_675 ?
N1 Zn1 N2 104.93(16) 2_675 . ?
N1 Zn1 N2 93.94(16) . . ?
N2 Zn1 N2 129.3(3) 2_675 . ?

_refine_diff_density_max         0.625
_refine_diff_density_min         -0.615
_refine_diff_density_rms         0.088


####################################################################### 
# 
# 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_compound3
_database_code_depnum_ccdc_archive 'CCDC 1893177'
loop_
_audit_author_name
_audit_author_address
'Stephane BAUDRON'
;University of Strasbourg
France
;
_audit_update_record             
;
2019-01-24 deposited with the CCDC.	2019-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H20 N4 Ni O2'
_chemical_formula_weight         551.23

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      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                   9.8321(3)
_cell_length_b                   10.7832(3)
_cell_length_c                   13.3416(3)
_cell_angle_alpha                103.1690(10)
_cell_angle_beta                 102.6240(10)
_cell_angle_gamma                111.8220(10)
_cell_volume                     1204.51(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6449
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      27.64

_exptl_crystal_description       platelet
_exptl_crystal_colour            dark-brown
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.846
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.934
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(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            23901
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.164
_diffrn_reflns_theta_max         30.170
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measured_fraction_theta_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.910
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_point_group_measured_fraction_full 0.957
_reflns_number_total             6497
_reflns_number_gt                4963
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.0419P)²+0.8415P] 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_number_reflns         6497
_refine_ls_number_parameters     352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1051
_refine_ls_wR_factor_gt          0.0946
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
C1 C 0.5103(3) 0.4248(2) 0.60549(18) 0.0260(5) Uani 1 1 d . . . . .
H1 H 0.533235 0.506298 0.664446 0.031 Uiso 1 1 calc R U . . .
C2 C 0.3721(3) 0.2977(2) 0.56732(18) 0.0273(5) Uani 1 1 d . . . . .
H2 H 0.289046 0.277719 0.595967 0.033 Uiso 1 1 calc R U . . .
C3 C 0.3814(3) 0.2086(2) 0.48049(18) 0.0270(5) Uani 1 1 d . . . . .
H3 H 0.305170 0.114533 0.437398 0.032 Uiso 1 1 calc R U . . .
C4 C 0.5257(2) 0.2823(2) 0.46643(18) 0.0240(4) Uani 1 1 d . . . . .
C5 C 0.5686(2) 0.2389(2) 0.37653(18) 0.0243(4) Uani 1 1 d . . . . .
C6 C 0.6957(3) 0.3283(2) 0.35528(17) 0.0244(4) Uani 1 1 d . . . . .
C7 C 0.7551(3) 0.3082(2) 0.26784(18) 0.0281(5) Uani 1 1 d . . . . .
H7 H 0.715804 0.222953 0.207720 0.034 Uiso 1 1 calc R U . . .
C8 C 0.8799(3) 0.4347(2) 0.28604(18) 0.0269(5) Uani 1 1 d . . . . .
H8 H 0.942217 0.453506 0.240993 0.032 Uiso 1 1 calc R U . . .
C9 C 0.8967(2) 0.5310(2) 0.38509(18) 0.0250(4) Uani 1 1 d . . . . .
C10 C 0.4683(2) 0.0928(2) 0.29601(18) 0.0247(4) Uani 1 1 d . . . . .
C11 C 0.4441(3) -0.0255(2) 0.32924(19) 0.0268(5) Uani 1 1 d . . . . .
H11 H 0.491494 -0.012213 0.403468 0.032 Uiso 1 1 calc R U . . .
C12 C 0.3519(3) -0.1613(2) 0.2551(2) 0.0286(5) Uani 1 1 d . . . . .
H12 H 0.336416 -0.241140 0.278226 0.034 Uiso 1 1 calc R U . . .
C13 C 0.2816(3) -0.1809(2) 0.1465(2) 0.0293(5) Uani 1 1 d . . . . .
C14 C 0.3039(3) -0.0640(3) 0.1130(2) 0.0338(5) Uani 1 1 d . . . . .
H14 H 0.254638 -0.077738 0.039008 0.041 Uiso 1 1 calc R U . . .
C15 C 0.3976(3) 0.0728(2) 0.18715(19) 0.0308(5) Uani 1 1 d . . . . .
H15 H 0.413522 0.152415 0.163763 0.037 Uiso 1 1 calc R U . . .
C16 C 0.1831(3) -0.3259(3) 0.0653(2) 0.0416(6) Uani 1 1 d . . . . .
H16 H 0.129140 -0.334556 -0.006230 0.050 Uiso 1 1 calc R U . . .
C17 C 0.9952(2) 0.6756(2) 0.45439(17) 0.0241(4) Uani 1 1 d . . . . .
C18 C 1.1079(3) 0.8002(2) 0.44929(19) 0.0283(5) Uani 1 1 d . . . . .
H18 H 1.152601 0.807102 0.393254 0.034 Uiso 1 1 calc R U . . .
C19 C 1.1397(3) 0.9092(2) 0.54128(18) 0.0280(5) Uani 1 1 d . . . . .
H19 H 1.209517 1.006379 0.560188 0.034 Uiso 1 1 calc R U . . .
C20 C 1.0488(2) 0.8495(2) 0.60318(18) 0.0245(4) Uani 1 1 d . . . . .
C21 C 1.0376(2) 0.9105(2) 0.70345(17) 0.0234(4) Uani 1 1 d . . . . .
C22 C 0.9467(2) 0.8305(2) 0.75432(18) 0.0251(4) Uani 1 1 d . . . . .
C23 C 0.9604(3) 0.8761(2) 0.86641(18) 0.0295(5) Uani 1 1 d . . . . .
H23 H 1.017079 0.970833 0.916423 0.035 Uiso 1 1 calc R U . . .
C24 C 0.8772(3) 0.7590(3) 0.88911(19) 0.0332(5) Uani 1 1 d . . . . .
H24 H 0.865985 0.756095 0.957596 0.040 Uiso 1 1 calc R U . . .
C25 C 0.8118(3) 0.6439(2) 0.79084(18) 0.0293(5) Uani 1 1 d . . . . .
H25 H 0.748562 0.548730 0.783484 0.035 Uiso 1 1 calc R U . . .
C26 C 1.1314(3) 1.0666(2) 0.76022(17) 0.0253(4) Uani 1 1 d . . . . .
C27 C 1.2913(3) 1.1308(2) 0.78079(19) 0.0294(5) Uani 1 1 d . . . . .
H27 H 1.342736 1.073547 0.764779 0.035 Uiso 1 1 calc R U . . .
C28 C 1.3755(3) 1.2767(2) 0.82417(19) 0.0315(5) Uani 1 1 d . . . . .
H28 H 1.484120 1.319623 0.836494 0.038 Uiso 1 1 calc R U . . .
C29 C 1.3012(3) 1.3606(2) 0.84980(18) 0.0295(5) Uani 1 1 d . . . . .
C30 C 1.1443(3) 1.2977(2) 0.83472(19) 0.0303(5) Uani 1 1 d . . . . .
H30 H 1.094622 1.355110 0.855273 0.036 Uiso 1 1 calc R U . . .
C31 C 1.0590(3) 1.1516(2) 0.78981(18) 0.0282(5) Uani 1 1 d . . . . .
H31 H 0.950882 1.109013 0.779081 0.034 Uiso 1 1 calc R U . . .
C32 C 1.3895(3) 1.5174(3) 0.8910(2) 0.0376(6) Uani 1 1 d . . . . .
H32 H 1.339497 1.571233 0.918035 0.045 Uiso 1 1 calc R U . . .
N1 N 0.6057(2) 0.41741(18) 0.54911(14) 0.0235(4) Uani 1 1 d . . . . .
N2 N 0.7862(2) 0.46554(18) 0.42564(14) 0.0240(4) Uani 1 1 d . . . . .
N3 N 0.9632(2) 0.70682(18) 0.54734(14) 0.0232(4) Uani 1 1 d . . . . .
N4 N 0.8488(2) 0.68385(18) 0.70849(15) 0.0246(4) Uani 1 1 d . . . . .
O1 O 0.1675(3) -0.4319(2) 0.0844(2) 0.0697(7) Uani 1 1 d . . . . .
O2 O 1.5192(3) 1.5812(2) 0.89256(19) 0.0609(6) Uani 1 1 d . . . . .
Ni1 Ni 0.79596(3) 0.56684(3) 0.56215(2) 0.02239(9) 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
C1 N1 1.337(3) . ?
C1 C2 1.407(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.370(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.423(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(3) . ?
C4 N1 1.412(3) . ?
C5 C6 1.399(3) . ?
C5 C10 1.489(3) . ?
C6 N2 1.373(3) . ?
C6 C7 1.423(3) . ?
C7 C8 1.378(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.415(3) . ?
C8 H8 0.9500 . ?
C9 N2 1.354(3) . ?
C9 C17 1.433(3) . ?
C10 C15 1.394(3) . ?
C10 C11 1.399(3) . ?
C11 C12 1.381(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.391(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(3) . ?
C13 C16 1.483(3) . ?
C14 C15 1.389(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 O1 1.190(3) . ?
C16 H16 0.9500 . ?
C17 N3 1.345(3) . ?
C17 C18 1.416(3) . ?
C18 C19 1.373(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.425(3) . ?
C19 H19 0.9500 . ?
C20 N3 1.368(3) . ?
C20 C21 1.397(3) . ?
C21 C22 1.401(3) . ?
C21 C26 1.489(3) . ?
C22 N4 1.404(3) . ?
C22 C23 1.423(3) . ?
C23 C24 1.368(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.403(3) . ?
C24 H24 0.9500 . ?
C25 N4 1.341(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.393(3) . ?
C26 C31 1.395(3) . ?
C27 C28 1.379(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.390(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.380(3) . ?
C29 C32 1.481(3) . ?
C30 C31 1.383(3) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 O2 1.196(3) . ?
C32 H32 0.9500 . ?
N1 Ni1 1.9016(17) . ?
N2 Ni1 1.8597(18) . ?
N3 Ni1 1.8584(17) . ?
N4 Ni1 1.9027(18) . ?

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 C1 C2 112.1(2) . . ?
N1 C1 H1 123.9 . . ?
C2 C1 H1 123.9 . . ?
C3 C2 C1 106.1(2) . . ?
C3 C2 H2 126.9 . . ?
C1 C2 H2 126.9 . . ?
C2 C3 C4 107.77(19) . . ?
C2 C3 H3 126.1 . . ?
C4 C3 H3 126.1 . . ?
C5 C4 N1 125.50(19) . . ?
C5 C4 C3 125.8(2) . . ?
N1 C4 C3 107.92(18) . . ?
C4 C5 C6 123.21(19) . . ?
C4 C5 C10 118.16(19) . . ?
C6 C5 C10 118.53(19) . . ?
N2 C6 C5 119.80(19) . . ?
N2 C6 C7 107.85(19) . . ?
C5 C6 C7 132.3(2) . . ?
C8 C7 C6 107.72(19) . . ?
C8 C7 H7 126.1 . . ?
C6 C7 H7 126.1 . . ?
C7 C8 C9 106.4(2) . . ?
C7 C8 H8 126.8 . . ?
C9 C8 H8 126.8 . . ?
N2 C9 C8 109.63(19) . . ?
N2 C9 C17 111.37(19) . . ?
C8 C9 C17 139.0(2) . . ?
C15 C10 C11 119.5(2) . . ?
C15 C10 C5 120.33(19) . . ?
C11 C10 C5 120.2(2) . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 119.8(2) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 120.0(2) . . ?
C14 C13 C16 119.3(2) . . ?
C12 C13 C16 120.7(2) . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C10 119.7(2) . . ?
C14 C15 H15 120.1 . . ?
C10 C15 H15 120.1 . . ?
O1 C16 C13 123.9(3) . . ?
O1 C16 H16 118.0 . . ?
C13 C16 H16 118.0 . . ?
N3 C17 C18 109.68(19) . . ?
N3 C17 C9 111.86(18) . . ?
C18 C17 C9 138.1(2) . . ?
C19 C18 C17 106.48(19) . . ?
C19 C18 H18 126.8 . . ?
C17 C18 H18 126.8 . . ?
C18 C19 C20 107.40(19) . . ?
C18 C19 H19 126.3 . . ?
C20 C19 H19 126.3 . . ?
N3 C20 C21 120.28(19) . . ?
N3 C20 C19 107.96(19) . . ?
C21 C20 C19 131.8(2) . . ?
C20 C21 C22 122.82(19) . . ?
C20 C21 C26 118.22(19) . . ?
C22 C21 C26 118.91(19) . . ?
C21 C22 N4 124.82(19) . . ?
C21 C22 C23 125.8(2) . . ?
N4 C22 C23 108.33(18) . . ?
C24 C23 C22 107.6(2) . . ?
C24 C23 H23 126.2 . . ?
C22 C23 H23 126.2 . . ?
C23 C24 C25 106.1(2) . . ?
C23 C24 H24 126.9 . . ?
C25 C24 H24 126.9 . . ?
N4 C25 C24 112.2(2) . . ?
N4 C25 H25 123.9 . . ?
C24 C25 H25 123.9 . . ?
C27 C26 C31 118.9(2) . . ?
C27 C26 C21 120.8(2) . . ?
C31 C26 C21 120.2(2) . . ?
C28 C27 C26 120.7(2) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C27 C28 C29 119.8(2) . . ?
C27 C28 H28 120.1 . . ?
C29 C28 H28 120.1 . . ?
C30 C29 C28 120.0(2) . . ?
C30 C29 C32 120.0(2) . . ?
C28 C29 C32 120.0(2) . . ?
C29 C30 C31 120.3(2) . . ?
C29 C30 H30 119.8 . . ?
C31 C30 H30 119.8 . . ?
C30 C31 C26 120.2(2) . . ?
C30 C31 H31 119.9 . . ?
C26 C31 H31 119.9 . . ?
O2 C32 C29 124.7(3) . . ?
O2 C32 H32 117.7 . . ?
C29 C32 H32 117.7 . . ?
C1 N1 C4 105.97(18) . . ?
C1 N1 Ni1 127.29(15) . . ?
C4 N1 Ni1 126.12(14) . . ?
C9 N2 C6 108.36(18) . . ?
C9 N2 Ni1 117.34(14) . . ?
C6 N2 Ni1 134.06(15) . . ?
C17 N3 C20 108.45(17) . . ?
C17 N3 Ni1 117.50(14) . . ?
C20 N3 Ni1 132.84(15) . . ?
C25 N4 C22 105.70(18) . . ?
C25 N4 Ni1 128.04(15) . . ?
C22 N4 Ni1 126.09(14) . . ?
N3 Ni1 N2 81.65(8) . . ?
N3 Ni1 N1 169.13(8) . . ?
N2 Ni1 N1 90.34(8) . . ?
N3 Ni1 N4 89.72(8) . . ?
N2 Ni1 N4 168.76(8) . . ?
N1 Ni1 N4 99.09(8) . . ?

_refine_diff_density_max         0.638
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.070


####################################################################### 
# 
# 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_compound4
_database_code_depnum_ccdc_archive 'CCDC 1893178'
loop_
_audit_author_name
_audit_author_address
'Stephane BAUDRON'
;University of Strasbourg
France
;
_audit_update_record             
;
2019-01-24 deposited with the CCDC.	2019-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H23 Cl3 N4 O2'
_chemical_formula_weight         613.90

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   11.4063(4)
_cell_length_b                   9.7778(3)
_cell_length_c                   13.4576(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.7850(10)
_cell_angle_gamma                90
_cell_volume                     1495.67(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9897
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      30.00


_exptl_crystal_description       cube
_exptl_crystal_colour            dark-purple
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.344
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(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            28945
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.748
_diffrn_reflns_theta_max         30.082
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             4084
_reflns_number_gt                3400
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.1036P)²+1.2813P] 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_number_reflns         4084
_refine_ls_number_parameters     208
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0701
_refine_ls_wR_factor_ref         0.2026
_refine_ls_wR_factor_gt          0.1929
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.044
_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
C1 C 0.51350(18) 0.7054(2) 0.39307(17) 0.0406(5) Uani 1 1 d . . . . .
H1 H 0.5943 0.7071 0.4168 0.049 Uiso 1 1 calc R U . . .
C2 C 0.4202(2) 0.7327(3) 0.44906(16) 0.0423(5) Uani 1 1 d . . . . .
H2 H 0.4252 0.7569 0.5177 0.051 Uiso 1 1 calc R U . . .
C3 C 0.31745(17) 0.7184(2) 0.38654(15) 0.0337(4) Uani 1 1 d . . . . .
H3 H 0.2395 0.7313 0.4047 0.040 Uiso 1 1 calc R U . . .
C4 C 0.34985(14) 0.68141(17) 0.29202(13) 0.0251(4) Uani 1 1 d . . . . .
C5 C 0.27774(13) 0.64743(15) 0.20373(12) 0.0216(3) Uani 1 1 d . . . . .
C6 C 0.31942(13) 0.59541(16) 0.11793(12) 0.0215(3) Uani 1 1 d . . . . .
C7 C 0.25216(14) 0.56145(18) 0.02552(13) 0.0255(4) Uani 1 1 d . . . . .
H7 H 0.1695 0.5702 0.0114 0.031 Uiso 1 1 calc R U . . .
C8 C 0.33025(15) 0.51467(19) -0.03709(13) 0.0268(4) Uani 1 1 d . . . . .
H8 H 0.3134 0.4843 -0.1038 0.032 Uiso 1 1 calc R U . . .
C9 C 0.44466(13) 0.52043(16) 0.01846(12) 0.0216(3) Uani 1 1 d . . . . .
C10 C 0.14894(13) 0.66659(16) 0.20893(12) 0.0226(3) Uani 1 1 d . . . . .
C11 C 0.07332(15) 0.55369(18) 0.20180(15) 0.0292(4) Uani 1 1 d . . . . .
H11 H 0.1034 0.4656 0.1885 0.035 Uiso 1 1 calc R U . . .
C12 C -0.04542(15) 0.5698(2) 0.21409(15) 0.0320(4) Uani 1 1 d . . . . .
H12 H -0.0964 0.4929 0.2097 0.038 Uiso 1 1 calc R U . . .
C13 C -0.08948(15) 0.6988(2) 0.23283(15) 0.0342(4) Uani 1 1 d . . . . .
C14 C -0.01575(17) 0.8112(2) 0.23693(19) 0.0435(6) Uani 1 1 d . . . . .
H14 H -0.0467 0.8997 0.2478 0.052 Uiso 1 1 calc R U . . .
C15 C 0.10325(16) 0.79547(19) 0.22529(18) 0.0374(5) Uani 1 1 d . . . . .
H15 H 0.1536 0.8731 0.2285 0.045 Uiso 1 1 calc R U . . .
C16 C -0.21398(18) 0.7176(3) 0.2509(2) 0.0546(7) Uani 1 1 d . . . . .
H16 H -0.2405 0.8087 0.2594 0.066 Uiso 1 1 calc R U . . .
N1 N 0.47078(13) 0.67577(17) 0.29927(12) 0.0304(4) Uani 1 1 d . . . . .
H1A H 0.5138 0.6558 0.2499 0.037 Uiso 1 1 calc R U . . .
N2 N 0.43877(12) 0.56855(14) 0.10978(11) 0.0220(3) Uani 1 1 d . . . . .
O1 O -0.28492(13) 0.6274(3) 0.25590(14) 0.0635(6) Uani 1 1 d . . . . .
C17 C -0.0004(10) 0.5303(12) 0.4756(6) 0.213(10) Uani 0.5 1 d D . P A -1
H17 H 0.0116 0.5673 0.4079 0.256 Uiso 0.5 1 calc R U P A -1
Cl1 Cl -0.0078(4) 0.3596(2) 0.4677(3) 0.1256(12) Uani 0.5 1 d . . P A -1
Cl2 Cl -0.1440(5) 0.5850(3) 0.5087(3) 0.1760(19) Uani 0.5 1 d D . P A -1
Cl3 Cl 0.0959(4) 0.6123(5) 0.5611(3) 0.1584(16) Uani 0.5 1 d . . P A -1


_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
C1 N1 1.346(3) . ?
C1 C2 1.380(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.392(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.401(2) . ?
C3 H3 0.9500 . ?
C4 N1 1.376(2) . ?
C4 C5 1.427(2) . ?
C5 C6 1.382(2) . ?
C5 C10 1.488(2) . ?
C6 N2 1.3997(19) . ?
C6 C7 1.444(2) . ?
C7 C8 1.356(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.450(2) . ?
C8 H8 0.9500 . ?
C9 N2 1.323(2) . ?
C9 C9 1.451(3) 3_665 ?
C10 C15 1.388(2) . ?
C10 C11 1.399(2) . ?
C11 C12 1.387(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(3) . ?
C13 C16 1.472(3) . ?
C14 C15 1.388(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 O1 1.203(3) . ?
C16 H16 0.9500 . ?
N1 H1A 0.8800 . ?
C17 Cl1 1.674(12) . ?
C17 Cl3 1.722(13) . ?
C17 Cl2 1.813(9) . ?
C17 H17 1.0000 . ?

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 C1 C2 108.56(19) . . ?
N1 C1 H1 125.7 . . ?
C2 C1 H1 125.7 . . ?
C1 C2 C3 107.41(19) . . ?
C1 C2 H2 126.3 . . ?
C3 C2 H2 126.3 . . ?
C2 C3 C4 107.59(16) . . ?
C2 C3 H3 126.2 . . ?
C4 C3 H3 126.2 . . ?
N1 C4 C3 106.54(16) . . ?
N1 C4 C5 123.69(15) . . ?
C3 C4 C5 129.69(15) . . ?
C6 C5 C4 124.53(14) . . ?
C6 C5 C10 119.69(15) . . ?
C4 C5 C10 115.74(14) . . ?
C5 C6 N2 122.63(15) . . ?
C5 C6 C7 127.52(14) . . ?
N2 C6 C7 109.85(13) . . ?
C8 C7 C6 106.46(14) . . ?
C8 C7 H7 126.8 . . ?
C6 C7 H7 126.8 . . ?
C7 C8 C9 106.04(15) . . ?
C7 C8 H8 127.0 . . ?
C9 C8 H8 127.0 . . ?
N2 C9 C8 112.30(13) . . ?
N2 C9 C9 121.95(19) . 3_665 ?
C8 C9 C9 125.75(19) . 3_665 ?
C15 C10 C11 119.31(15) . . ?
C15 C10 C5 120.44(14) . . ?
C11 C10 C5 120.18(14) . . ?
C12 C11 C10 120.29(16) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 119.79(17) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 120.08(16) . . ?
C14 C13 C16 119.09(19) . . ?
C12 C13 C16 120.8(2) . . ?
C13 C14 C15 120.33(18) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C10 120.14(17) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
O1 C16 C13 125.5(2) . . ?
O1 C16 H16 117.3 . . ?
C13 C16 H16 117.3 . . ?
C1 N1 C4 109.89(16) . . ?
C1 N1 H1A 125.1 . . ?
C4 N1 H1A 125.1 . . ?
C9 N2 C6 105.35(13) . . ?
Cl1 C17 Cl3 122.2(6) . . ?
Cl1 C17 Cl2 105.6(7) . . ?
Cl3 C17 Cl2 103.7(6) . . ?
Cl1 C17 H17 108.2 . . ?
Cl3 C17 H17 108.2 . . ?
Cl2 C17 H17 108.2 . . ?

_refine_diff_density_max         0.756
_refine_diff_density_min         -0.735
_refine_diff_density_rms         0.068





#===END




####################################################################### 
# 
# 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_compound2
_database_code_depnum_ccdc_archive 'CCDC 1893176'
loop_
_audit_author_name
_audit_author_address
'Stephane BAUDRON'
;University of Strasbourg
France
;
_audit_update_record             
;
2019-01-24 deposited with the CCDC.	2019-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H22 N4 Ni O2'
_chemical_formula_weight         553.24

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      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                   9.7819(2)
_cell_length_b                   11.6608(3)
_cell_length_c                   12.9613(3)
_cell_angle_alpha                110.8970(10)
_cell_angle_beta                 98.8930(10)
_cell_angle_gamma                111.0520(10)
_cell_volume                     1219.34(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9952
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      30.14

_exptl_crystal_description       platelet
_exptl_crystal_colour            dark-red
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_F_000             572
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.836
_shelx_estimated_absorpt_T_min   0.885
_shelx_estimated_absorpt_T_max   0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.884
_exptl_absorpt_correction_T_max  0.943
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(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            24117
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.778
_diffrn_reflns_theta_max         30.160
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measured_fraction_theta_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_point_group_measured_fraction_full 0.958
_reflns_number_total             6572
_reflns_number_gt                5711
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.0317P)²+0.7739P] 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_number_reflns         6572
_refine_ls_number_parameters     352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.0800
_refine_ls_wR_factor_gt          0.0768
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
C1 C 0.97373(18) 0.75599(16) 0.17006(15) 0.0217(3) Uani 1 1 d . . . . .
H1 H 1.064347 0.832183 0.180780 0.026 Uiso 1 1 calc R U . . .
C2 C 0.95363(19) 0.62010(16) 0.12650(15) 0.0236(3) Uani 1 1 d . . . . .
H2 H 1.025664 0.588477 0.102417 0.028 Uiso 1 1 calc R U . . .
C3 C 0.80895(18) 0.54171(16) 0.12557(15) 0.0214(3) Uani 1 1 d . . . . .
H3 H 0.762453 0.445491 0.101404 0.026 Uiso 1 1 calc R U . . .
C4 C 0.74242(17) 0.63161(14) 0.16748(13) 0.0172(3) Uani 1 1 d . . . . .
C5 C 0.59166(17) 0.59832(14) 0.17318(13) 0.0170(3) Uani 1 1 d . . . . .
C6 C 0.52648(17) 0.68873(15) 0.18701(13) 0.0172(3) Uani 1 1 d . . . . .
C7 C 0.38478(18) 0.67560(16) 0.20916(14) 0.0209(3) Uani 1 1 d . . . . .
H7 H 0.310712 0.598325 0.212109 0.025 Uiso 1 1 calc R U . . .
C8 C 0.37474(18) 0.79422(16) 0.22537(15) 0.0229(3) Uani 1 1 d . . . . .
H8 H 0.293053 0.815434 0.241866 0.027 Uiso 1 1 calc R U . . .
C9 C 0.50971(17) 0.87911(15) 0.21279(14) 0.0198(3) Uani 1 1 d . . . . .
H9 H 0.532819 0.968679 0.220292 0.024 Uiso 1 1 calc R U . . .
C10 C 0.50227(17) 0.46252(15) 0.16980(13) 0.0177(3) Uani 1 1 d . . . . .
C11 C 0.57585(18) 0.41748(15) 0.23722(14) 0.0205(3) Uani 1 1 d . . . . .
H11 H 0.682818 0.471693 0.281151 0.025 Uiso 1 1 calc R U . . .
C12 C 0.49465(19) 0.29512(16) 0.24056(14) 0.0223(3) Uani 1 1 d . . . . .
H12 H 0.546082 0.264931 0.285696 0.027 Uiso 1 1 calc R U . . .
C13 C 0.33784(19) 0.21636(15) 0.17788(15) 0.0218(3) Uani 1 1 d . . . . .
C14 C 0.26408(19) 0.25833(16) 0.10889(15) 0.0224(3) Uani 1 1 d . . . . .
H14 H 0.157209 0.203384 0.064881 0.027 Uiso 1 1 calc R U . . .
C15 C 0.34566(18) 0.38025(15) 0.10383(14) 0.0201(3) Uani 1 1 d . . . . .
H15 H 0.294931 0.407711 0.055486 0.024 Uiso 1 1 calc R U . . .
C16 C 0.2496(2) 0.08730(17) 0.18419(17) 0.0277(4) Uani 1 1 d . . . . .
H16 H 0.142278 0.035941 0.140724 0.033 Uiso 1 1 calc R U . . .
C17 C 1.09120(17) 1.02049(16) 0.40748(14) 0.0195(3) Uani 1 1 d . . . . .
H17 H 1.069198 0.930524 0.398398 0.023 Uiso 1 1 calc R U . . .
C18 C 1.20776(18) 1.14219(16) 0.50333(14) 0.0228(3) Uani 1 1 d . . . . .
H18 H 1.275780 1.148572 0.568230 0.027 Uiso 1 1 calc R U . . .
C19 C 1.20319(18) 1.24866(16) 0.48414(14) 0.0212(3) Uani 1 1 d . . . . .
H19 H 1.267657 1.343666 0.533632 0.025 Uiso 1 1 calc R U . . .
C20 C 1.08378(17) 1.19111(15) 0.37604(14) 0.0174(3) Uani 1 1 d . . . . .
C21 C 1.03563(17) 1.25940(15) 0.32097(14) 0.0180(3) Uani 1 1 d . . . . .
C22 C 0.90510(17) 1.19121(15) 0.22073(14) 0.0191(3) Uani 1 1 d . . . . .
C23 C 0.86379(19) 1.24048(17) 0.14151(15) 0.0247(3) Uani 1 1 d . . . . .
H23 H 0.917204 1.330119 0.148149 0.030 Uiso 1 1 calc R U . . .
C24 C 0.7317(2) 1.13420(18) 0.05308(15) 0.0265(4) Uani 1 1 d . . . . .
H24 H 0.676783 1.136001 -0.013053 0.032 Uiso 1 1 calc R U . . .
C25 C 0.69454(18) 1.02284(16) 0.08007(14) 0.0220(3) Uani 1 1 d . . . . .
H25 H 0.607623 0.935679 0.033678 0.026 Uiso 1 1 calc R U . . .
C26 C 1.12387(18) 1.41126(15) 0.36925(14) 0.0197(3) Uani 1 1 d . . . . .
C27 C 1.28521(18) 1.47662(15) 0.40240(14) 0.0213(3) Uani 1 1 d . . . . .
H27 H 1.341127 1.423792 0.392822 0.026 Uiso 1 1 calc R U . . .
C28 C 1.36438(19) 1.61921(16) 0.44950(15) 0.0237(3) Uani 1 1 d . . . . .
H28 H 1.474273 1.663281 0.473169 0.028 Uiso 1 1 calc R U . . .
C29 C 1.2842(2) 1.69697(16) 0.46204(15) 0.0244(3) Uani 1 1 d . . . . .
C30 C 1.1236(2) 1.63309(16) 0.42780(15) 0.0257(4) Uani 1 1 d . . . . .
H30 H 1.068160 1.686288 0.435426 0.031 Uiso 1 1 calc R U . . .
C31 C 1.0443(2) 1.49130(16) 0.38241(16) 0.0247(3) Uani 1 1 d . . . . .
H31 H 0.934438 1.448002 0.359965 0.030 Uiso 1 1 calc R U . . .
C32 C 1.3706(2) 1.84815(17) 0.50940(17) 0.0339(4) Uani 1 1 d . . . . .
H32 H 1.480489 1.888400 0.532711 0.041 Uiso 1 1 calc R U . . .
N1 N 0.84802(14) 0.76415(12) 0.19459(12) 0.0176(3) Uani 1 1 d . . . . .
N2 N 0.60097(14) 0.81800(12) 0.18904(11) 0.0165(3) Uani 1 1 d . . . . .
N3 N 1.01575(14) 1.04763(12) 0.33121(11) 0.0170(3) Uani 1 1 d . . . . .
N4 N 0.79734(15) 1.05493(13) 0.17984(12) 0.0183(3) Uani 1 1 d . . . . .
O1 O 0.30573(16) 0.04354(13) 0.24118(13) 0.0342(3) Uani 1 1 d . . . . .
O2 O 1.30954(19) 1.92278(13) 0.52000(14) 0.0468(4) Uani 1 1 d . . . . .
Ni1 Ni 0.81585(2) 0.92086(2) 0.22226(2) 0.01577(6) 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
C1 N1 1.344(2) . ?
C1 C2 1.404(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.377(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.418(2) . ?
C3 H3 0.9500 . ?
C4 N1 1.3902(18) . ?
C4 C5 1.405(2) . ?
C5 C6 1.391(2) . ?
C5 C10 1.4893(19) . ?
C6 N2 1.4073(18) . ?
C6 C7 1.424(2) . ?
C7 C8 1.365(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.412(2) . ?
C8 H8 0.9500 . ?
C9 N2 1.336(2) . ?
C9 H9 0.9500 . ?
C10 C15 1.397(2) . ?
C10 C11 1.401(2) . ?
C11 C12 1.382(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(2) . ?
C13 C16 1.481(2) . ?
C14 C15 1.389(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 O1 1.205(2) . ?
C16 H16 0.9500 . ?
C17 N3 1.3370(19) . ?
C17 C18 1.414(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.365(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.427(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.392(2) . ?
C20 N3 1.4024(18) . ?
C21 C22 1.404(2) . ?
C21 C26 1.489(2) . ?
C22 N4 1.3930(18) . ?
C22 C23 1.417(2) . ?
C23 C24 1.377(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.402(2) . ?
C24 H24 0.9500 . ?
C25 N4 1.3439(19) . ?
C25 H25 0.9500 . ?
C26 C27 1.396(2) . ?
C26 C31 1.399(2) . ?
C27 C28 1.393(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.382(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.389(2) . ?
C29 C32 1.482(2) . ?
C30 C31 1.388(2) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 O2 1.203(2) . ?
C32 H32 0.9500 . ?
N1 Ni1 1.8835(12) . ?
N2 Ni1 1.8927(12) . ?
N3 Ni1 1.8930(12) . ?
N4 Ni1 1.8881(12) . ?

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 C1 C2 111.14(14) . . ?
N1 C1 H1 124.4 . . ?
C2 C1 H1 124.4 . . ?
C3 C2 C1 106.48(15) . . ?
C3 C2 H2 126.8 . . ?
C1 C2 H2 126.8 . . ?
C2 C3 C4 107.12(13) . . ?
C2 C3 H3 126.4 . . ?
C4 C3 H3 126.4 . . ?
N1 C4 C5 122.82(13) . . ?
N1 C4 C3 108.60(13) . . ?
C5 C4 C3 128.36(13) . . ?
C6 C5 C4 122.82(13) . . ?
C6 C5 C10 119.31(14) . . ?
C4 C5 C10 117.80(13) . . ?
C5 C6 N2 123.31(14) . . ?
C5 C6 C7 128.47(14) . . ?
N2 C6 C7 108.08(13) . . ?
C8 C7 C6 107.58(14) . . ?
C8 C7 H7 126.2 . . ?
C6 C7 H7 126.2 . . ?
C7 C8 C9 106.43(14) . . ?
C7 C8 H8 126.8 . . ?
C9 C8 H8 126.8 . . ?
N2 C9 C8 111.67(13) . . ?
N2 C9 H9 124.2 . . ?
C8 C9 H9 124.2 . . ?
C15 C10 C11 118.91(13) . . ?
C15 C10 C5 121.89(13) . . ?
C11 C10 C5 119.17(13) . . ?
C12 C11 C10 120.76(14) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 119.92(14) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 119.94(14) . . ?
C14 C13 C16 120.06(15) . . ?
C12 C13 C16 120.00(15) . . ?
C13 C14 C15 120.37(15) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C10 120.04(14) . . ?
C14 C15 H15 120.0 . . ?
C10 C15 H15 120.0 . . ?
O1 C16 C13 123.91(17) . . ?
O1 C16 H16 118.0 . . ?
C13 C16 H16 118.0 . . ?
N3 C17 C18 111.66(13) . . ?
N3 C17 H17 124.2 . . ?
C18 C17 H17 124.2 . . ?
C19 C18 C17 106.39(14) . . ?
C19 C18 H18 126.8 . . ?
C17 C18 H18 126.8 . . ?
C18 C19 C20 107.45(13) . . ?
C18 C19 H19 126.3 . . ?
C20 C19 H19 126.3 . . ?
C21 C20 N3 123.37(13) . . ?
C21 C20 C19 128.35(14) . . ?
N3 C20 C19 108.27(13) . . ?
C20 C21 C22 122.77(13) . . ?
C20 C21 C26 119.60(13) . . ?
C22 C21 C26 117.63(13) . . ?
N4 C22 C21 122.99(13) . . ?
N4 C22 C23 108.61(13) . . ?
C21 C22 C23 128.29(14) . . ?
C24 C23 C22 107.23(14) . . ?
C24 C23 H23 126.4 . . ?
C22 C23 H23 126.4 . . ?
C23 C24 C25 106.33(14) . . ?
C23 C24 H24 126.8 . . ?
C25 C24 H24 126.8 . . ?
N4 C25 C24 111.46(14) . . ?
N4 C25 H25 124.3 . . ?
C24 C25 H25 124.3 . . ?
C27 C26 C31 118.77(14) . . ?
C27 C26 C21 121.59(14) . . ?
C31 C26 C21 119.64(14) . . ?
C28 C27 C26 120.11(15) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C29 C28 C27 120.48(15) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C28 C29 C30 120.00(14) . . ?
C28 C29 C32 119.52(16) . . ?
C30 C29 C32 120.46(16) . . ?
C31 C30 C29 119.76(16) . . ?
C31 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?
C30 C31 C26 120.87(16) . . ?
C30 C31 H31 119.6 . . ?
C26 C31 H31 119.6 . . ?
O2 C32 C29 123.71(19) . . ?
O2 C32 H32 118.1 . . ?
C29 C32 H32 118.1 . . ?
C1 N1 C4 106.65(13) . . ?
C1 N1 Ni1 122.43(10) . . ?
C4 N1 Ni1 129.20(10) . . ?
C9 N2 C6 106.23(13) . . ?
C9 N2 Ni1 121.58(10) . . ?
C6 N2 Ni1 126.89(10) . . ?
C17 N3 C20 106.23(12) . . ?
C17 N3 Ni1 123.04(10) . . ?
C20 N3 Ni1 126.97(10) . . ?
C25 N4 C22 106.36(12) . . ?
C25 N4 Ni1 122.80(11) . . ?
C22 N4 Ni1 128.41(10) . . ?
N1 Ni1 N4 152.48(6) . . ?
N1 Ni1 N2 91.43(5) . . ?
N4 Ni1 N2 95.48(5) . . ?
N1 Ni1 N3 95.25(5) . . ?
N4 Ni1 N3 91.81(5) . . ?
N2 Ni1 N3 150.31(6) . . ?

_refine_diff_density_max         0.414
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.060


