# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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. 
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data_mo_2015202_0m
_database_code_depnum_ccdc_archive 'CCDC 1400951'
_audit_update_record             
;
2017-02-27 deposited with the CCDC.
2017-03-01 downloaded from the CCDC.
;
_audit_creation_date             2017-02-27
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.02.06 svn.r3384 for OlexSys, GUI svn.r5312)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C31 H30 Cl3 N3 Ni O3'
_chemical_formula_sum            'C31 H30 Cl3 N3 Ni O3'
_chemical_formula_weight         657.64
_chemical_absolute_configuration .
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   7.844(2)
_cell_length_b                   10.872(2)
_cell_length_c                   34.637(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2953.8(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4039
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.78
_cell_measurement_theta_min      2.212
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.966
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1019 before and 0.0625 after correction. The Ratio of minimum to maximum transmission is 0.7823. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0700
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            14233
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.545
_diffrn_reflns_theta_min         1.963
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'CCD area dector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.744
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                4833
_reflns_number_total             6666
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Flack x determined using 1539 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.022(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         6666
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0471P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1109
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
 C26(H26), C27(H27), C30(H30)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.25778(10) 0.34069(5) 0.82819(2) 0.03771(18) Uani 1 1 d . . . . .
Cl1 Cl 0.7742(2) 0.44883(17) 0.89902(4) 0.0797(5) Uani 1 1 d . . . . .
Cl2 Cl 0.7184(3) 0.7329(2) 0.91311(6) 0.0998(7) Uani 1 1 d . . . . .
Cl3 Cl 0.4315(2) 0.64064(14) 1.00501(4) 0.0665(5) Uani 1 1 d . . . . .
O1 O 0.0216(5) 0.6557(3) 0.83373(10) 0.0516(9) Uani 1 1 d . . . . .
O2 O 0.3455(6) 0.2006(3) 0.80477(9) 0.0588(12) Uani 1 1 d . . . . .
O3 O 0.4096(9) 0.0064(4) 0.81701(12) 0.108(2) Uani 1 1 d . . . . .
N1 N 0.2585(7) 0.4311(3) 0.77988(10) 0.0444(10) Uani 1 1 d . . . . .
N2 N 0.1805(5) 0.4822(3) 0.85158(10) 0.0313(9) Uani 1 1 d . . . . .
N3 N 0.2681(6) 0.2534(3) 0.87369(9) 0.0349(9) Uani 1 1 d . . . . .
C1 C 0.2181(6) 0.5147(4) 0.88948(12) 0.0331(11) Uani 1 1 d . . . . .
C2 C 0.1987(7) 0.6364(4) 0.90295(14) 0.0435(13) Uani 1 1 d . . . . .
H2 H 0.1408 0.6932 0.8877 0.052 Uiso 1 1 calc R . . . .
C3 C 0.2631(8) 0.6728(4) 0.93787(14) 0.0499(13) Uani 1 1 d . . . . .
H3 H 0.2512 0.7544 0.9455 0.060 Uiso 1 1 calc R . . . .
C4 C 0.3442(7) 0.5920(5) 0.96153(14) 0.0447(13) Uani 1 1 d . . . . .
C5 C 0.3552(7) 0.4709(4) 0.95118(13) 0.0374(11) Uani 1 1 d . . . . .
H5 H 0.4047 0.4149 0.9681 0.045 Uiso 1 1 calc R . . . .
C6 C 0.2928(6) 0.4292(4) 0.91525(12) 0.0312(11) Uani 1 1 d . . . . .
C7 C 0.3007(6) 0.2974(4) 0.90770(13) 0.0343(11) Uani 1 1 d . . . . .
C8 C 0.3535(7) 0.2128(4) 0.93977(13) 0.0367(12) Uani 1 1 d . . . . .
C9 C 0.5077(8) 0.1501(5) 0.93707(15) 0.0523(14) Uani 1 1 d . . . . .
H9 H 0.5806 0.1644 0.9164 0.063 Uiso 1 1 calc R . . . .
C10 C 0.5521(9) 0.0661(6) 0.96546(17) 0.0635(17) Uani 1 1 d . . . . .
H10 H 0.6541 0.0230 0.9635 0.076 Uiso 1 1 calc R . . . .
C11 C 0.4470(9) 0.0459(5) 0.99637(17) 0.0625(17) Uani 1 1 d . . . . .
H11 H 0.4767 -0.0115 1.0151 0.075 Uiso 1 1 calc R . . . .
C12 C 0.2980(8) 0.1108(5) 0.99959(15) 0.0577(16) Uani 1 1 d . . . . .
H12 H 0.2277 0.0979 1.0208 0.069 Uiso 1 1 calc R . . . .
C13 C 0.2509(9) 0.1950(4) 0.97171(12) 0.0461(12) Uani 1 1 d . . . . .
H13 H 0.1505 0.2396 0.9744 0.055 Uiso 1 1 calc R . . . .
C14 C 0.2554(9) 0.1195(3) 0.86530(12) 0.0449(13) Uani 1 1 d . . . . .
H14 H 0.3197 0.0742 0.8850 0.054 Uiso 1 1 calc R . . . .
C15 C 0.0686(9) 0.0723(4) 0.86516(15) 0.0565(17) Uani 1 1 d . . . . .
C16 C -0.0179(10) 0.0977(6) 0.90351(17) 0.079(2) Uani 1 1 d . . . . .
H16A H -0.0191 0.1848 0.9082 0.118 Uiso 1 1 calc GR . . . .
H16B H 0.0433 0.0571 0.9238 0.118 Uiso 1 1 calc GR . . . .
H16C H -0.1329 0.0675 0.9027 0.118 Uiso 1 1 calc GR . . . .
C17 C 0.0737(13) -0.0669(5) 0.8587(2) 0.104(3) Uani 1 1 d . . . . .
H17A H -0.0405 -0.0977 0.8562 0.156 Uiso 1 1 calc GR . . . .
H17B H 0.1286 -0.1058 0.8802 0.156 Uiso 1 1 calc GR . . . .
H17C H 0.1362 -0.0845 0.8355 0.156 Uiso 1 1 calc GR . . . .
C18 C -0.0390(10) 0.1316(6) 0.83358(18) 0.080(2) Uani 1 1 d . . . . .
H18A H 0.0174 0.1224 0.8091 0.120 Uiso 1 1 calc GR . . . .
H18B H -0.0538 0.2174 0.8392 0.120 Uiso 1 1 calc GR . . . .
H18C H -0.1485 0.0922 0.8326 0.120 Uiso 1 1 calc GR . . . .
C19 C 0.1023(7) 0.5636(4) 0.82617(14) 0.0384(11) Uani 1 1 d . . . . .
C20 C 0.1206(7) 0.5248(4) 0.78466(13) 0.0390(12) Uani 1 1 d . . . . .
H20 H 0.1481 0.5971 0.7690 0.047 Uiso 1 1 calc R . . . .
C21 C -0.0419(8) 0.4646(6) 0.76883(16) 0.0638(17) Uani 1 1 d . . . . .
H21A H -0.1208 0.4471 0.7897 0.077 Uiso 1 1 calc R . . . .
H21B H -0.0975 0.5189 0.7505 0.077 Uiso 1 1 calc R . . . .
C22 C 0.0123(11) 0.3476(6) 0.74935(17) 0.0709(19) Uani 1 1 d . . . . .
H22A H -0.0421 0.3396 0.7243 0.085 Uiso 1 1 calc R . . . .
H22B H -0.0175 0.2767 0.7650 0.085 Uiso 1 1 calc R . . . .
C23 C 0.2037(10) 0.3578(5) 0.74498(13) 0.064(2) Uani 1 1 d . . . . .
H23A H 0.2565 0.2771 0.7449 0.077 Uiso 1 1 calc R . . . .
H23B H 0.2333 0.4003 0.7213 0.077 Uiso 1 1 calc R . . . .
C24 C 0.4324(8) 0.4845(6) 0.77273(15) 0.0602(17) Uani 1 1 d . . . . .
H24A H 0.5090 0.4188 0.7652 0.072 Uiso 1 1 calc R . . . .
H24B H 0.4254 0.5420 0.7514 0.072 Uiso 1 1 calc R . . . .
C25 C 0.5053(7) 0.5489(5) 0.80672(15) 0.0508(14) Uani 1 1 d . . . . .
C26 C 0.4878(9) 0.6746(6) 0.81285(19) 0.0652(18) Uani 1 1 d . . . . .
H26 H 0.4303 0.7219 0.7947 0.078 Uiso 1 1 calc R . . . .
C27 C 0.5533(10) 0.7300(6) 0.8450(2) 0.072(2) Uani 1 1 d . . . . .
H27 H 0.5387 0.8142 0.8484 0.086 Uiso 1 1 calc R . . . .
C28 C 0.6404(8) 0.6631(6) 0.87222(18) 0.0633(16) Uani 1 1 d . . . . .
C29 C 0.6624(7) 0.5380(6) 0.86670(16) 0.0553(15) Uani 1 1 d . . . . .
C30 C 0.5961(8) 0.4820(5) 0.83414(15) 0.0529(14) Uani 1 1 d . . . . .
H30 H 0.6126 0.3981 0.8305 0.063 Uiso 1 1 calc R . . . .
C31 C 0.3441(9) 0.1038(5) 0.82651(15) 0.0617(18) 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 O2 1.858(3) . ?
Ni1 N1 1.941(3) . ?
Ni1 N2 1.841(3) . ?
Ni1 N3 1.841(3) . ?
Cl1 C29 1.721(6) . ?
Cl2 C28 1.720(7) . ?
Cl3 C4 1.737(5) . ?
O1 C19 1.213(5) . ?
O2 C31 1.294(6) . ?
O3 C31 1.222(6) . ?
N1 C20 1.494(7) . ?
N1 C23 1.511(6) . ?
N1 C24 1.503(8) . ?
N2 C1 1.391(5) . ?
N2 C19 1.391(6) . ?
N3 C7 1.297(5) . ?
N3 C14 1.488(5) . ?
C1 C2 1.411(6) . ?
C1 C6 1.416(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.370(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.359(7) . ?
C4 C5 1.368(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.412(6) . ?
C6 C7 1.457(6) . ?
C7 C8 1.501(6) . ?
C8 C9 1.392(8) . ?
C8 C13 1.381(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.386(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.369(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.370(9) . ?
C12 H12 0.9300 . ?
C12 C13 1.381(7) . ?
C13 H13 0.9300 . ?
C14 H14 0.9800 . ?
C14 C15 1.552(9) . ?
C14 C31 1.523(7) . ?
C15 C16 1.517(8) . ?
C15 C17 1.530(7) . ?
C15 C18 1.525(8) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.505(7) . ?
C20 H20 0.9800 . ?
C20 C21 1.534(8) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.502(8) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.513(10) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.484(8) . ?
C25 C26 1.389(8) . ?
C25 C30 1.392(7) . ?
C26 H26 0.9300 . ?
C26 C27 1.366(9) . ?
C27 H27 0.9300 . ?
C27 C28 1.374(9) . ?
C28 C29 1.384(9) . ?
C29 C30 1.383(8) . ?
C30 H30 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 N1 92.17(14) . . ?
N2 Ni1 O2 177.5(2) . . ?
N2 Ni1 N1 87.54(15) . . ?
N2 Ni1 N3 93.93(14) . . ?
N3 Ni1 O2 86.27(14) . . ?
N3 Ni1 N1 177.3(2) . . ?
C31 O2 Ni1 114.2(3) . . ?
C20 N1 Ni1 104.3(3) . . ?
C20 N1 C23 104.0(4) . . ?
C20 N1 C24 114.3(4) . . ?
C23 N1 Ni1 114.9(3) . . ?
C24 N1 Ni1 109.9(3) . . ?
C24 N1 C23 109.3(4) . . ?
C1 N2 Ni1 123.9(3) . . ?
C1 N2 C19 121.9(4) . . ?
C19 N2 Ni1 113.5(3) . . ?
C7 N3 Ni1 126.6(3) . . ?
C7 N3 C14 123.5(3) . . ?
C14 N3 Ni1 109.5(2) . . ?
N2 C1 C2 121.8(4) . . ?
N2 C1 C6 121.1(4) . . ?
C2 C1 C6 116.9(4) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 C1 121.6(4) . . ?
C3 C2 H2 119.2 . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.2(4) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 Cl3 120.7(4) . . ?
C3 C4 C5 119.6(5) . . ?
C5 C4 Cl3 119.7(4) . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.2(5) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C7 123.4(4) . . ?
C5 C6 C1 119.2(4) . . ?
C5 C6 C7 117.3(4) . . ?
N3 C7 C6 121.2(4) . . ?
N3 C7 C8 120.0(4) . . ?
C6 C7 C8 118.8(4) . . ?
C9 C8 C7 119.4(4) . . ?
C13 C8 C7 121.2(5) . . ?
C13 C8 C9 119.4(5) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.5(5) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.6(6) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.7(5) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.8(5) . . ?
C13 C12 H12 119.6 . . ?
C8 C13 H13 120.1 . . ?
C12 C13 C8 119.8(5) . . ?
C12 C13 H13 120.1 . . ?
N3 C14 H14 108.8 . . ?
N3 C14 C15 112.8(5) . . ?
N3 C14 C31 104.6(4) . . ?
C15 C14 H14 108.8 . . ?
C31 C14 H14 108.8 . . ?
C31 C14 C15 113.0(5) . . ?
C16 C15 C14 111.1(5) . . ?
C16 C15 C17 108.7(6) . . ?
C16 C15 C18 107.6(6) . . ?
C17 C15 C14 107.6(6) . . ?
C18 C15 C14 112.6(5) . . ?
C18 C15 C17 109.1(5) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O1 C19 N2 128.2(5) . . ?
O1 C19 C20 119.2(4) . . ?
N2 C19 C20 112.6(4) . . ?
N1 C20 C19 111.5(4) . . ?
N1 C20 H20 109.0 . . ?
N1 C20 C21 105.7(4) . . ?
C19 C20 H20 109.0 . . ?
C19 C20 C21 112.4(5) . . ?
C21 C20 H20 109.0 . . ?
C20 C21 H21A 110.4 . . ?
C20 C21 H21B 110.4 . . ?
H21A C21 H21B 108.6 . . ?
C22 C21 C20 106.7(5) . . ?
C22 C21 H21A 110.4 . . ?
C22 C21 H21B 110.4 . . ?
C21 C22 H22A 110.7 . . ?
C21 C22 H22B 110.7 . . ?
C21 C22 C23 105.3(5) . . ?
H22A C22 H22B 108.8 . . ?
C23 C22 H22A 110.7 . . ?
C23 C22 H22B 110.7 . . ?
N1 C23 C22 104.0(5) . . ?
N1 C23 H23A 111.0 . . ?
N1 C23 H23B 111.0 . . ?
C22 C23 H23A 111.0 . . ?
C22 C23 H23B 111.0 . . ?
H23A C23 H23B 109.0 . . ?
N1 C24 H24A 108.8 . . ?
N1 C24 H24B 108.8 . . ?
H24A C24 H24B 107.7 . . ?
C25 C24 N1 113.7(4) . . ?
C25 C24 H24A 108.8 . . ?
C25 C24 H24B 108.8 . . ?
C26 C25 C24 123.1(6) . . ?
C26 C25 C30 117.4(6) . . ?
C30 C25 C24 119.5(5) . . ?
C25 C26 H26 119.3 . . ?
C27 C26 C25 121.4(6) . . ?
C27 C26 H26 119.3 . . ?
C26 C27 H27 119.6 . . ?
C26 C27 C28 120.9(6) . . ?
C28 C27 H27 119.6 . . ?
C27 C28 Cl2 120.6(6) . . ?
C27 C28 C29 119.2(6) . . ?
C29 C28 Cl2 120.2(5) . . ?
C28 C29 Cl1 121.8(5) . . ?
C30 C29 Cl1 118.3(5) . . ?
C30 C29 C28 119.9(6) . . ?
C25 C30 H30 119.4 . . ?
C29 C30 C25 121.3(5) . . ?
C29 C30 H30 119.4 . . ?
O2 C31 C14 115.2(4) . . ?
O3 C31 O2 123.0(5) . . ?
O3 C31 C14 121.8(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ni1 O2 C31 O3 -173.7(6) . . . . ?
Ni1 O2 C31 C14 5.9(7) . . . . ?
Ni1 N1 C20 C19 31.0(5) . . . . ?
Ni1 N1 C20 C21 -91.4(4) . . . . ?
Ni1 N1 C23 C22 75.0(5) . . . . ?
Ni1 N1 C24 C25 -47.6(6) . . . . ?
Ni1 N2 C1 C2 161.9(4) . . . . ?
Ni1 N2 C1 C6 -12.2(6) . . . . ?
Ni1 N2 C19 O1 170.1(4) . . . . ?
Ni1 N2 C19 C20 -7.9(5) . . . . ?
Ni1 N3 C7 C6 15.3(7) . . . . ?
Ni1 N3 C7 C8 -162.6(4) . . . . ?
Ni1 N3 C14 C15 -89.8(4) . . . . ?
Ni1 N3 C14 C31 33.4(6) . . . . ?
Cl1 C29 C30 C25 -179.6(4) . . . . ?
Cl2 C28 C29 Cl1 -2.6(7) . . . . ?
Cl2 C28 C29 C30 178.6(4) . . . . ?
Cl3 C4 C5 C6 -177.0(4) . . . . ?
O1 C19 C20 N1 165.1(5) . . . . ?
O1 C19 C20 C21 -76.4(6) . . . . ?
O2 Ni1 N3 C7 146.1(5) . . . . ?
O2 Ni1 N3 C14 -26.6(4) . . . . ?
N1 Ni1 O2 C31 -170.1(5) . . . . ?
N1 Ni1 N2 C1 -148.6(4) . . . . ?
N1 Ni1 N2 C19 22.0(4) . . . . ?
N1 C20 C21 C22 -9.4(6) . . . . ?
N1 C24 C25 C26 -93.4(6) . . . . ?
N1 C24 C25 C30 86.6(6) . . . . ?
N2 Ni1 N3 C7 -31.4(5) . . . . ?
N2 Ni1 N3 C14 155.9(4) . . . . ?
N2 C1 C2 C3 -168.4(5) . . . . ?
N2 C1 C6 C5 169.4(4) . . . . ?
N2 C1 C6 C7 -14.1(7) . . . . ?
N2 C19 C20 N1 -16.7(6) . . . . ?
N2 C19 C20 C21 101.8(5) . . . . ?
N3 Ni1 O2 C31 12.1(5) . . . . ?
N3 Ni1 N2 C1 29.0(4) . . . . ?
N3 Ni1 N2 C19 -160.3(3) . . . . ?
N3 C7 C8 C9 65.2(7) . . . . ?
N3 C7 C8 C13 -114.0(6) . . . . ?
N3 C14 C15 C16 -57.8(5) . . . . ?
N3 C14 C15 C17 -176.6(4) . . . . ?
N3 C14 C15 C18 63.0(5) . . . . ?
N3 C14 C31 O2 -25.6(7) . . . . ?
N3 C14 C31 O3 154.0(7) . . . . ?
C1 N2 C19 O1 -19.0(8) . . . . ?
C1 N2 C19 C20 162.9(4) . . . . ?
C1 C2 C3 C4 -2.0(9) . . . . ?
C1 C6 C7 N3 13.0(7) . . . . ?
C1 C6 C7 C8 -169.1(5) . . . . ?
C2 C1 C6 C5 -4.9(7) . . . . ?
C2 C1 C6 C7 171.5(5) . . . . ?
C2 C3 C4 Cl3 177.8(4) . . . . ?
C2 C3 C4 C5 -3.0(9) . . . . ?
C3 C4 C5 C6 3.8(8) . . . . ?
C4 C5 C6 C1 0.3(7) . . . . ?
C4 C5 C6 C7 -176.4(5) . . . . ?
C5 C6 C7 N3 -170.5(5) . . . . ?
C5 C6 C7 C8 7.4(7) . . . . ?
C6 C1 C2 C3 5.9(8) . . . . ?
C6 C7 C8 C9 -112.7(5) . . . . ?
C6 C7 C8 C13 68.0(6) . . . . ?
C7 N3 C14 C15 97.3(6) . . . . ?
C7 N3 C14 C31 -139.5(5) . . . . ?
C7 C8 C9 C10 -176.0(5) . . . . ?
C7 C8 C13 C12 176.0(5) . . . . ?
C8 C9 C10 C11 -1.1(9) . . . . ?
C9 C8 C13 C12 -3.3(8) . . . . ?
C9 C10 C11 C12 -1.0(9) . . . . ?
C10 C11 C12 C13 1.0(9) . . . . ?
C11 C12 C13 C8 1.2(8) . . . . ?
C13 C8 C9 C10 3.3(8) . . . . ?
C14 N3 C7 C6 -173.0(5) . . . . ?
C14 N3 C7 C8 9.1(8) . . . . ?
C15 C14 C31 O2 97.5(6) . . . . ?
C15 C14 C31 O3 -82.9(8) . . . . ?
C19 N2 C1 C2 -8.0(7) . . . . ?
C19 N2 C1 C6 177.9(4) . . . . ?
C19 C20 C21 C22 -131.3(5) . . . . ?
C20 N1 C23 C22 -38.5(5) . . . . ?
C20 N1 C24 C25 69.3(6) . . . . ?
C20 C21 C22 C23 -14.3(6) . . . . ?
C21 C22 C23 N1 32.5(6) . . . . ?
C23 N1 C20 C19 151.9(4) . . . . ?
C23 N1 C20 C21 29.4(5) . . . . ?
C23 N1 C24 C25 -174.6(5) . . . . ?
C24 N1 C20 C19 -89.0(5) . . . . ?
C24 N1 C20 C21 148.6(4) . . . . ?
C24 N1 C23 C22 -161.0(5) . . . . ?
C24 C25 C26 C27 178.4(5) . . . . ?
C24 C25 C30 C29 -178.3(5) . . . . ?
C25 C26 C27 C28 0.6(10) . . . . ?
C26 C25 C30 C29 1.7(8) . . . . ?
C26 C27 C28 Cl2 -178.6(5) . . . . ?
C26 C27 C28 C29 0.4(9) . . . . ?
C27 C28 C29 Cl1 178.5(5) . . . . ?
C27 C28 C29 C30 -0.3(9) . . . . ?
C28 C29 C30 C25 -0.7(8) . . . . ?
C30 C25 C26 C27 -1.6(9) . . . . ?
C31 C14 C15 C16 -176.1(5) . . . . ?
C31 C14 C15 C17 65.0(6) . . . . ?
C31 C14 C15 C18 -55.3(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cd15097
_database_code_depnum_ccdc_archive 'CCDC 1422992'
_audit_update_record             
;
2015-09-08 deposited with the CCDC.
2017-03-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H33 Cl3 N4 Ni O4'
_chemical_formula_weight         762.73

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   10.143(6)
_cell_length_b                   9.381(5)
_cell_length_c                   17.036(9)
_cell_angle_alpha                90
_cell_angle_beta                 96.513(8)
_cell_angle_gamma                90
_cell_volume                     1610.5(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    981
_cell_measurement_theta_min      4.463
_cell_measurement_theta_max      37.124

_exptl_crystal_description       prismatic
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_F_000             788
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.901
_shelx_estimated_absorpt_T_min   0.826
_shelx_estimated_absorpt_T_max   0.907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6288
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6826
_diffrn_reflns_av_unetI/netI     0.1100
_diffrn_reflns_av_R_equivalents  0.0719
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.021
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.745
_diffrn_reflns_point_group_measured_fraction_full 0.729
_reflns_number_total             4256
_reflns_number_gt                3151
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.404
_reflns_Friedel_fraction_max     0.460
_reflns_Friedel_fraction_full    0.449

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0866P)²+1.4143P] 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 683 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.04(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4256
_refine_ls_number_parameters     420
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0820
_refine_ls_wR_factor_ref         0.1915
_refine_ls_wR_factor_gt          0.1770
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.16304(13) 0.21645(19) 0.66794(7) 0.0301(4) Uani 1 1 d . . . . .
Cl1 Cl 0.1163(5) 0.1999(6) 1.07089(19) 0.0772(14) Uani 1 1 d . . . . .
Cl2 Cl -0.1438(8) 0.0100(8) 0.8487(3) 0.129(3) Uani 1 1 d . . . . .
Cl3 Cl -0.2481(6) 0.2777(8) 0.9222(3) 0.120(3) Uani 1 1 d . . . . .
N1 N 0.2613(9) 0.0944(12) 0.7335(5) 0.030(2) Uani 1 1 d . . . . .
N2 N 0.1484(10) 0.3515(12) 0.7431(5) 0.033(3) Uani 1 1 d . . . . .
N3 N 0.0531(10) 0.3356(13) 0.5995(6) 0.040(3) Uani 1 1 d . . . . .
N5 N 0.5719(12) 0.299(2) 0.5555(7) 0.060(4) Uani 1 1 d . . . . .
H5A H 0.6018 0.3244 0.5123 0.072 Uiso 1 1 calc R U . . .
O1 O 0.2878(9) -0.1040(12) 0.5631(5) 0.052(3) Uani 1 1 d . . . . .
O2 O 0.1755(9) 0.0839(11) 0.5913(5) 0.042(2) Uani 1 1 d . . . . .
O3 O 0.1218(10) 0.5926(11) 0.7475(5) 0.052(3) Uani 1 1 d . . . . .
O4 O 0.9773(18) 0.8294(18) 0.6813(10) 0.111(5) Uani 1 1 d . . . . .
H4 H 1.0285 0.7648 0.6962 0.166 Uiso 1 1 calc R U . . .
C1 C 0.2600(15) -0.0131(16) 0.6083(7) 0.044(4) Uani 1 1 d . . . . .
C2 C 0.3298(11) -0.0087(14) 0.6884(6) 0.032(3) Uani 1 1 d . . . . .
H2 H 0.3246 -0.1030 0.7126 0.038 Uiso 1 1 calc R U . . .
C3 C 0.2689(11) 0.0886(14) 0.8080(6) 0.030(3) Uani 1 1 d . . . . .
C4 C 0.2054(11) 0.1924(13) 0.8532(6) 0.029(3) Uani 1 1 d . . . . .
C5 C 0.1909(12) 0.1606(16) 0.9296(6) 0.039(3) Uani 1 1 d . . . . .
H5 H 0.2197 0.0723 0.9495 0.047 Uiso 1 1 calc R U . . .
C6 C 0.1375(12) 0.2502(14) 0.9764(7) 0.039(3) Uani 1 1 d . . . . .
C7 C 0.0979(13) 0.3790(17) 0.9499(7) 0.044(3) Uani 1 1 d . . . . .
H7 H 0.0631 0.4432 0.9837 0.053 Uiso 1 1 calc R U . . .
C8 C 0.1083(12) 0.4171(17) 0.8735(7) 0.043(3) Uani 1 1 d . . . . .
H8 H 0.0817 0.5076 0.8560 0.052 Uiso 1 1 calc R U . . .
C9 C 0.1572(11) 0.3237(15) 0.8227(6) 0.032(3) Uani 1 1 d . . . . .
C10 C 0.1226(12) 0.4802(16) 0.7138(7) 0.037(3) Uani 1 1 d . . . . .
C11 C 0.0821(12) 0.4794(15) 0.6256(6) 0.035(3) Uani 1 1 d . . . . .
H11 H 0.0050 0.5412 0.6120 0.042 Uiso 1 1 calc R U . . .
C12 C 0.1978(16) 0.5269(19) 0.5826(8) 0.055(4) Uani 1 1 d . . . . .
H12A H 0.1814 0.6204 0.5591 0.066 Uiso 1 1 calc R U . . .
H12B H 0.2795 0.5300 0.6182 0.066 Uiso 1 1 calc R U . . .
C13 C 0.2047(14) 0.418(2) 0.5215(8) 0.060(5) Uani 1 1 d . . . . .
H13A H 0.2160 0.4617 0.4711 0.073 Uiso 1 1 calc R U . . .
H13B H 0.2788 0.3539 0.5358 0.073 Uiso 1 1 calc R U . . .
C14 C 0.0805(14) 0.3404(19) 0.5164(7) 0.052(4) Uani 1 1 d . . . . .
H14A H 0.0898 0.2453 0.4954 0.062 Uiso 1 1 calc R U . . .
H14B H 0.0109 0.3905 0.4836 0.062 Uiso 1 1 calc R U . . .
C15 C -0.0862(12) 0.2947(18) 0.6025(7) 0.046(4) Uani 1 1 d . . . . .
H15A H -0.1427 0.3631 0.5722 0.055 Uiso 1 1 calc R U . . .
H15B H -0.1012 0.2024 0.5775 0.055 Uiso 1 1 calc R U . . .
C16 C -0.1254(8) 0.2872(12) 0.6819(4) 0.041(4) Uani 1 1 d G . . . .
C17 C -0.1175(9) 0.1599(10) 0.7239(5) 0.057(4) Uani 1 1 d G . . . .
H17 H -0.0861 0.0780 0.7014 0.068 Uiso 1 1 calc R U . . .
C18 C -0.1566(10) 0.1549(12) 0.7994(5) 0.066(5) Uani 1 1 d G . . . .
C19 C -0.2035(9) 0.2772(15) 0.8330(4) 0.070(6) Uani 1 1 d G . . . .
C20 C -0.2114(8) 0.4045(13) 0.7910(6) 0.069(5) Uani 1 1 d G . . . .
H20 H -0.2429 0.4863 0.8134 0.083 Uiso 1 1 calc R U . . .
C21 C -0.1723(9) 0.4095(10) 0.7154(6) 0.069(5) Uani 1 1 d G . . . .
H21 H -0.1776 0.4947 0.6873 0.083 Uiso 1 1 calc R U . . .
C22 C 0.4750(12) 0.0301(17) 0.6865(7) 0.041(3) Uani 1 1 d . . . . .
H22A H 0.5160 0.0377 0.7406 0.049 Uiso 1 1 calc R U . . .
H22B H 0.5178 -0.0482 0.6622 0.049 Uiso 1 1 calc R U . . .
C23 C 0.5038(13) 0.1626(17) 0.6448(7) 0.040(4) Uani 1 1 d . . . . .
C24 C 0.5471(12) 0.165(2) 0.5751(8) 0.054(5) Uani 1 1 d . . . . .
H24 H 0.5588 0.0853 0.5441 0.065 Uiso 1 1 calc R U . . .
C25 C 0.5434(13) 0.391(2) 0.6134(10) 0.059(5) Uani 1 1 d . . . . .
C26 C 0.4986(12) 0.3047(16) 0.6718(7) 0.032(3) Uani 1 1 d . . . . .
C27 C 0.4677(13) 0.3691(18) 0.7384(8) 0.049(4) Uani 1 1 d . . . . .
H27 H 0.4375 0.3160 0.7789 0.058 Uiso 1 1 calc R U . . .
C28 C 0.4818(16) 0.514(2) 0.7450(11) 0.067(5) Uani 1 1 d . . . . .
H28 H 0.4614 0.5595 0.7906 0.080 Uiso 1 1 calc R U . . .
C29 C 0.5239(18) 0.591(2) 0.6877(14) 0.081(6) Uani 1 1 d . . . . .
H29 H 0.5339 0.6886 0.6950 0.097 Uiso 1 1 calc R U . . .
C30 C 0.5520(16) 0.536(2) 0.6217(12) 0.072(6) Uani 1 1 d . . . . .
H30 H 0.5771 0.5932 0.5814 0.086 Uiso 1 1 calc R U . . .
C31 C 0.3389(8) -0.0237(8) 0.8507(4) 0.037(3) Uani 1 1 d G . . . .
C32 C 0.4647(8) 0.0031(9) 0.8892(5) 0.050(4) Uani 1 1 d G . . . .
H32 H 0.5023 0.0931 0.8864 0.059 Uiso 1 1 calc R U . . .
C33 C 0.5342(7) -0.1046(12) 0.9320(5) 0.064(5) Uani 1 1 d G . . . .
H33 H 0.6184 -0.0867 0.9577 0.076 Uiso 1 1 calc R U . . .
C34 C 0.4780(10) -0.2392(10) 0.9362(5) 0.069(5) Uani 1 1 d G . . . .
H34 H 0.5245 -0.3112 0.9647 0.083 Uiso 1 1 calc R U . . .
C35 C 0.3522(10) -0.2660(8) 0.8976(5) 0.062(4) Uani 1 1 d G . . . .
H35 H 0.3146 -0.3560 0.9004 0.074 Uiso 1 1 calc R U . . .
C36 C 0.2826(7) -0.1583(9) 0.8549(4) 0.043(3) Uani 1 1 d G . . . .
H36 H 0.1985 -0.1762 0.8291 0.052 Uiso 1 1 calc R U . . .
C37 C 0.849(3) 0.785(3) 0.6846(14) 0.126(9) Uani 1 1 d . . . . .
H37A H 0.8493 0.6992 0.7154 0.189 Uiso 1 1 calc R U . . .
H37B H 0.8075 0.7668 0.6321 0.189 Uiso 1 1 calc R U . . .
H37C H 0.8007 0.8578 0.7087 0.189 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 N1 1.817(10) . ?
Ni1 O2 1.818(9) . ?
Ni1 N2 1.819(10) . ?
Ni1 N3 1.886(11) . ?
Cl1 C6 1.714(12) . ?
Cl2 C18 1.595(11) . ?
Cl3 C19 1.634(8) . ?
N1 C3 1.264(13) . ?
N1 C2 1.460(15) . ?
N2 C10 1.321(17) . ?
N2 C9 1.375(14) . ?
N3 C11 1.441(17) . ?
N3 C15 1.471(15) . ?
N3 C14 1.474(15) . ?
N5 C24 1.33(2) . ?
N5 C25 1.37(2) . ?
N5 H5A 0.8600 . ?
O1 C1 1.204(16) . ?
O2 C1 1.261(17) . ?
O3 C10 1.201(17) . ?
O4 C37 1.37(3) . ?
O4 H4 0.8200 . ?
C1 C2 1.465(17) . ?
C2 C22 1.521(16) . ?
C2 H2 0.9800 . ?
C3 C31 1.423(14) . ?
C3 C4 1.438(17) . ?
C4 C5 1.360(15) . ?
C4 C9 1.402(18) . ?
C5 C6 1.317(17) . ?
C5 H5 0.9300 . ?
C6 C7 1.336(19) . ?
C7 C8 1.364(17) . ?
C7 H7 0.9300 . ?
C8 C9 1.365(18) . ?
C8 H8 0.9300 . ?
C10 C11 1.512(16) . ?
C11 C12 1.519(18) . ?
C11 H11 0.9800 . ?
C12 C13 1.47(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.45(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.453(13) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.3900 . ?
C16 C21 1.3900 . ?
C17 C18 1.3900 . ?
C17 H17 0.9300 . ?
C18 C19 1.3900 . ?
C19 C20 1.3900 . ?
C20 C21 1.3900 . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.48(2) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.312(18) . ?
C23 C26 1.41(2) . ?
C24 H24 0.9300 . ?
C25 C30 1.37(3) . ?
C25 C26 1.40(2) . ?
C26 C27 1.353(19) . ?
C27 C28 1.37(2) . ?
C27 H27 0.9300 . ?
C28 C29 1.32(2) . ?
C28 H28 0.9300 . ?
C29 C30 1.30(2) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C31 C32 1.3900 . ?
C31 C36 1.3900 . ?
C32 C33 1.3900 . ?
C32 H32 0.9300 . ?
C33 C34 1.3900 . ?
C33 H33 0.9300 . ?
C34 C35 1.3900 . ?
C34 H34 0.9300 . ?
C35 C36 1.3900 . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ni1 O2 86.1(4) . . ?
N1 Ni1 N2 95.1(4) . . ?
O2 Ni1 N2 178.7(5) . . ?
N1 Ni1 N3 176.8(5) . . ?
O2 Ni1 N3 92.6(4) . . ?
N2 Ni1 N3 86.1(5) . . ?
C3 N1 C2 121.5(11) . . ?
C3 N1 Ni1 127.7(9) . . ?
C2 N1 Ni1 110.7(7) . . ?
C10 N2 C9 122.3(12) . . ?
C10 N2 Ni1 113.6(8) . . ?
C9 N2 Ni1 124.1(9) . . ?
C11 N3 C15 113.4(11) . . ?
C11 N3 C14 102.4(11) . . ?
C15 N3 C14 109.2(9) . . ?
C11 N3 Ni1 106.1(7) . . ?
C15 N3 Ni1 109.0(9) . . ?
C14 N3 Ni1 116.7(9) . . ?
C24 N5 C25 110.8(12) . . ?
C24 N5 H5A 124.6 . . ?
C25 N5 H5A 124.6 . . ?
C1 O2 Ni1 115.4(8) . . ?
C37 O4 H4 109.5 . . ?
O1 C1 O2 124.5(13) . . ?
O1 C1 C2 119.5(14) . . ?
O2 C1 C2 116.0(12) . . ?
N1 C2 C1 107.5(10) . . ?
N1 C2 C22 111.8(10) . . ?
C1 C2 C22 110.7(9) . . ?
N1 C2 H2 108.9 . . ?
C1 C2 H2 108.9 . . ?
C22 C2 H2 108.9 . . ?
N1 C3 C31 121.0(12) . . ?
N1 C3 C4 121.9(11) . . ?
C31 C3 C4 117.1(9) . . ?
C5 C4 C9 118.4(11) . . ?
C5 C4 C3 117.9(11) . . ?
C9 C4 C3 123.8(10) . . ?
C6 C5 C4 122.5(13) . . ?
C6 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
C5 C6 C7 120.1(12) . . ?
C5 C6 Cl1 119.8(10) . . ?
C7 C6 Cl1 120.1(10) . . ?
C6 C7 C8 120.4(13) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C9 120.6(14) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C9 N2 121.1(13) . . ?
C8 C9 C4 117.8(11) . . ?
N2 C9 C4 120.8(11) . . ?
O3 C10 N2 129.4(12) . . ?
O3 C10 C11 117.6(13) . . ?
N2 C10 C11 113.0(12) . . ?
N3 C11 C10 109.6(11) . . ?
N3 C11 C12 105.5(11) . . ?
C10 C11 C12 109.9(10) . . ?
N3 C11 H11 110.6 . . ?
C10 C11 H11 110.6 . . ?
C12 C11 H11 110.6 . . ?
C13 C12 C11 103.8(13) . . ?
C13 C12 H12A 111.0 . . ?
C11 C12 H12A 111.0 . . ?
C13 C12 H12B 111.0 . . ?
C11 C12 H12B 111.0 . . ?
H12A C12 H12B 109.0 . . ?
C14 C13 C12 106.3(12) . . ?
C14 C13 H13A 110.5 . . ?
C12 C13 H13A 110.5 . . ?
C14 C13 H13B 110.5 . . ?
C12 C13 H13B 110.5 . . ?
H13A C13 H13B 108.7 . . ?
C13 C14 N3 102.4(11) . . ?
C13 C14 H14A 111.3 . . ?
N3 C14 H14A 111.3 . . ?
C13 C14 H14B 111.3 . . ?
N3 C14 H14B 111.3 . . ?
H14A C14 H14B 109.2 . . ?
C16 C15 N3 114.3(9) . . ?
C16 C15 H15A 108.7 . . ?
N3 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
N3 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C17 C16 C21 120.0 . . ?
C17 C16 C15 121.0(9) . . ?
C21 C16 C15 119.0(9) . . ?
C18 C17 C16 120.0 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.0 . . ?
C17 C18 Cl2 120.1(8) . . ?
C19 C18 Cl2 119.9(8) . . ?
C20 C19 C18 120.0 . . ?
C20 C19 Cl3 118.1(8) . . ?
C18 C19 Cl3 121.9(8) . . ?
C19 C20 C21 120.0 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C16 120.0 . . ?
C20 C21 H21 120.0 . . ?
C16 C21 H21 120.0 . . ?
C23 C22 C2 117.2(12) . . ?
C23 C22 H22A 108.0 . . ?
C2 C22 H22A 108.0 . . ?
C23 C22 H22B 108.0 . . ?
C2 C22 H22B 108.0 . . ?
H22A C22 H22B 107.2 . . ?
C24 C23 C26 107.9(14) . . ?
C24 C23 C22 123.7(16) . . ?
C26 C23 C22 128.3(11) . . ?
C23 C24 N5 109.5(15) . . ?
C23 C24 H24 125.2 . . ?
N5 C24 H24 125.2 . . ?
N5 C25 C30 133.3(17) . . ?
N5 C25 C26 105.1(16) . . ?
C30 C25 C26 121.6(17) . . ?
C27 C26 C25 117.6(15) . . ?
C27 C26 C23 135.6(13) . . ?
C25 C26 C23 106.7(12) . . ?
C26 C27 C28 118.7(15) . . ?
C26 C27 H27 120.7 . . ?
C28 C27 H27 120.7 . . ?
C29 C28 C27 121.2(18) . . ?
C29 C28 H28 119.4 . . ?
C27 C28 H28 119.4 . . ?
C30 C29 C28 123(2) . . ?
C30 C29 H29 118.5 . . ?
C28 C29 H29 118.5 . . ?
C29 C30 C25 117.8(18) . . ?
C29 C30 H30 121.1 . . ?
C25 C30 H30 121.1 . . ?
C32 C31 C36 120.0 . . ?
C32 C31 C3 119.0(7) . . ?
C36 C31 C3 121.0(7) . . ?
C33 C32 C31 120.0 . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C32 C33 C34 120.0 . . ?
C32 C33 H33 120.0 . . ?
C34 C33 H33 120.0 . . ?
C35 C34 C33 120.0 . . ?
C35 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C34 C35 C36 120.0 . . ?
C34 C35 H35 120.0 . . ?
C36 C35 H35 120.0 . . ?
C35 C36 C31 120.0 . . ?
C35 C36 H36 120.0 . . ?
C31 C36 H36 120.0 . . ?
O4 C37 H37A 109.5 . . ?
O4 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
O4 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 Ni1 N1 C3 -158.0(11) . . . . ?
N2 Ni1 N1 C3 22.0(11) . . . . ?
O2 Ni1 N1 C2 18.7(8) . . . . ?
N2 Ni1 N1 C2 -161.3(8) . . . . ?
N1 Ni1 N2 C10 157.6(9) . . . . ?
N3 Ni1 N2 C10 -25.4(9) . . . . ?
N1 Ni1 N2 C9 -25.1(10) . . . . ?
N3 Ni1 N2 C9 151.9(10) . . . . ?
O2 Ni1 N3 C11 -148.9(8) . . . . ?
N2 Ni1 N3 C11 31.0(8) . . . . ?
O2 Ni1 N3 C15 88.7(9) . . . . ?
N2 Ni1 N3 C15 -91.4(9) . . . . ?
O2 Ni1 N3 C14 -35.6(10) . . . . ?
N2 Ni1 N3 C14 144.4(10) . . . . ?
N1 Ni1 O2 C1 -12.9(10) . . . . ?
N3 Ni1 O2 C1 170.1(10) . . . . ?
Ni1 O2 C1 O1 -174.9(11) . . . . ?
Ni1 O2 C1 C2 3.2(15) . . . . ?
C3 N1 C2 C1 156.4(11) . . . . ?
Ni1 N1 C2 C1 -20.5(11) . . . . ?
C3 N1 C2 C22 -81.9(14) . . . . ?
Ni1 N1 C2 C22 101.2(10) . . . . ?
O1 C1 C2 N1 -170.4(11) . . . . ?
O2 C1 C2 N1 11.4(15) . . . . ?
O1 C1 C2 C22 67.2(16) . . . . ?
O2 C1 C2 C22 -111.0(13) . . . . ?
C2 N1 C3 C31 -3.5(16) . . . . ?
Ni1 N1 C3 C31 172.8(8) . . . . ?
C2 N1 C3 C4 177.9(10) . . . . ?
Ni1 N1 C3 C4 -5.8(17) . . . . ?
N1 C3 C4 C5 164.4(11) . . . . ?
C31 C3 C4 C5 -14.3(15) . . . . ?
N1 C3 C4 C9 -15.2(18) . . . . ?
C31 C3 C4 C9 166.1(10) . . . . ?
C9 C4 C5 C6 -2.3(18) . . . . ?
C3 C4 C5 C6 178.1(11) . . . . ?
C4 C5 C6 C7 -2(2) . . . . ?
C4 C5 C6 Cl1 177.3(10) . . . . ?
C5 C6 C7 C8 2(2) . . . . ?
Cl1 C6 C7 C8 -176.6(10) . . . . ?
C6 C7 C8 C9 1(2) . . . . ?
C7 C8 C9 N2 169.4(12) . . . . ?
C7 C8 C9 C4 -4.7(18) . . . . ?
C10 N2 C9 C8 16.4(18) . . . . ?
Ni1 N2 C9 C8 -160.6(10) . . . . ?
C10 N2 C9 C4 -169.7(11) . . . . ?
Ni1 N2 C9 C4 13.3(16) . . . . ?
C5 C4 C9 C8 5.3(17) . . . . ?
C3 C4 C9 C8 -175.1(11) . . . . ?
C5 C4 C9 N2 -168.8(11) . . . . ?
C3 C4 C9 N2 10.8(18) . . . . ?
C9 N2 C10 O3 12(2) . . . . ?
Ni1 N2 C10 O3 -170.9(12) . . . . ?
C9 N2 C10 C11 -164.9(10) . . . . ?
Ni1 N2 C10 C11 12.5(13) . . . . ?
C15 N3 C11 C10 89.1(12) . . . . ?
C14 N3 C11 C10 -153.4(10) . . . . ?
Ni1 N3 C11 C10 -30.5(11) . . . . ?
C15 N3 C11 C12 -152.6(10) . . . . ?
C14 N3 C11 C12 -35.1(13) . . . . ?
Ni1 N3 C11 C12 87.7(10) . . . . ?
O3 C10 C11 N3 -164.0(12) . . . . ?
N2 C10 C11 N3 13.1(15) . . . . ?
O3 C10 C11 C12 80.5(16) . . . . ?
N2 C10 C11 C12 -102.4(14) . . . . ?
N3 C11 C12 C13 12.8(14) . . . . ?
C10 C11 C12 C13 130.9(13) . . . . ?
C11 C12 C13 C14 15.1(15) . . . . ?
C12 C13 C14 N3 -36.9(16) . . . . ?
C11 N3 C14 C13 44.6(14) . . . . ?
C15 N3 C14 C13 165.0(13) . . . . ?
Ni1 N3 C14 C13 -70.9(14) . . . . ?
C11 N3 C15 C16 -66.2(15) . . . . ?
C14 N3 C15 C16 -179.7(13) . . . . ?
Ni1 N3 C15 C16 51.8(14) . . . . ?
N3 C15 C16 C17 -92.3(13) . . . . ?
N3 C15 C16 C21 88.2(12) . . . . ?
C21 C16 C17 C18 0.0 . . . . ?
C15 C16 C17 C18 -179.5(9) . . . . ?
C16 C17 C18 C19 0.0 . . . . ?
C16 C17 C18 Cl2 -178.3(8) . . . . ?
C17 C18 C19 C20 0.0 . . . . ?
Cl2 C18 C19 C20 178.3(8) . . . . ?
C17 C18 C19 Cl3 -178.8(7) . . . . ?
Cl2 C18 C19 Cl3 -0.5(8) . . . . ?
C18 C19 C20 C21 0.0 . . . . ?
Cl3 C19 C20 C21 178.9(7) . . . . ?
C19 C20 C21 C16 0.0 . . . . ?
C17 C16 C21 C20 0.0 . . . . ?
C15 C16 C21 C20 179.5(8) . . . . ?
N1 C2 C22 C23 -65.5(14) . . . . ?
C1 C2 C22 C23 54.3(16) . . . . ?
C2 C22 C23 C24 -105.2(15) . . . . ?
C2 C22 C23 C26 78.8(18) . . . . ?
C26 C23 C24 N5 0.7(18) . . . . ?
C22 C23 C24 N5 -176.0(13) . . . . ?
C25 N5 C24 C23 -0.6(19) . . . . ?
C24 N5 C25 C30 179.7(16) . . . . ?
C24 N5 C25 C26 0.2(17) . . . . ?
N5 C25 C26 C27 177.6(12) . . . . ?
C30 C25 C26 C27 -2(2) . . . . ?
N5 C25 C26 C23 0.3(16) . . . . ?
C30 C25 C26 C23 -179.3(14) . . . . ?
C24 C23 C26 C27 -177.2(15) . . . . ?
C22 C23 C26 C27 -1(3) . . . . ?
C24 C23 C26 C25 -0.6(16) . . . . ?
C22 C23 C26 C25 175.9(13) . . . . ?
C25 C26 C27 C28 0(2) . . . . ?
C23 C26 C27 C28 176.3(16) . . . . ?
C26 C27 C28 C29 0(2) . . . . ?
C27 C28 C29 C30 1(3) . . . . ?
C28 C29 C30 C25 -3(3) . . . . ?
N5 C25 C30 C29 -175.8(16) . . . . ?
C26 C25 C30 C29 4(2) . . . . ?
N1 C3 C31 C32 102.7(11) . . . . ?
C4 C3 C31 C32 -78.6(11) . . . . ?
N1 C3 C31 C36 -78.0(12) . . . . ?
C4 C3 C31 C36 100.7(10) . . . . ?
C36 C31 C32 C33 0.0 . . . . ?
C3 C31 C32 C33 179.3(9) . . . . ?
C31 C32 C33 C34 0.0 . . . . ?
C32 C33 C34 C35 0.0 . . . . ?
C33 C34 C35 C36 0.0 . . . . ?
C34 C35 C36 C31 0.0 . . . . ?
C32 C31 C36 C35 0.0 . . . . ?
C3 C31 C36 C35 -179.3(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C37 H37C Cl2 0.96 2.78 3.50(3) 131.9 1_665
C17 H17 O4 0.93 2.45 3.35(2) 161.7 1_445
C15 H15A O1 0.97 2.61 3.426(15) 142.1 2_556
C14 H14A O2 0.97 2.32 2.840(19) 112.6 .
C8 H8 O3 0.93 2.09 2.722(17) 123.6 .
C7 H7 Cl2 0.93 2.95 3.624(13) 130.9 2_557
O4 H4 O3 0.82 2.02 2.825(19) 167.0 1_655
N5 H5A O1 0.86 1.92 2.754(14) 163.3 2_656
C37 H37C Cl2 0.96 2.78 3.50(3) 131.9 1_665
C17 H17 O4 0.93 2.45 3.35(2) 161.7 1_445
C15 H15A O1 0.97 2.61 3.426(15) 142.1 2_556
C14 H14A O2 0.97 2.32 2.840(19) 112.6 .
C8 H8 O3 0.93 2.09 2.722(17) 123.6 .
C7 H7 Cl2 0.93 2.95 3.624(13) 130.9 2_557
O4 H4 O3 0.82 2.02 2.825(19) 167.0 1_655
N5 H5A O1 0.86 1.92 2.754(14) 163.3 2_656
N5 H5A O1 0.86 1.92 2.754(14) 163.3 2_656
O4 H4 O3 0.82 2.02 2.825(19) 167.0 1_655
C7 H7 Cl2 0.93 2.95 3.624(13) 130.9 2_557
C8 H8 O3 0.93 2.09 2.722(17) 123.6 .
C14 H14A O2 0.97 2.32 2.840(19) 112.6 .
C15 H15A O1 0.97 2.61 3.426(15) 142.1 2_556
C17 H17 O4 0.93 2.45 3.35(2) 161.7 1_445
C37 H37C Cl2 0.96 2.78 3.50(3) 131.9 1_665

_refine_diff_density_max         0.639
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.094

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_cd16655
_database_code_depnum_ccdc_archive 'CCDC 1520062'
_audit_update_record             
;
2016-11-30 deposited with the CCDC.
2017-03-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H22 Cl3 N3 Ni O3'
_chemical_formula_weight         601.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   11.0422(14)
_cell_length_b                   7.6034(10)
_cell_length_c                   15.9516(19)
_cell_angle_alpha                90
_cell_angle_beta                 100.367(3)
_cell_angle_gamma                90
_cell_volume                     1317.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2425
_cell_measurement_theta_min      4.930
_cell_measurement_theta_max      46.076

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.076
_shelx_estimated_absorpt_T_min   0.798
_shelx_estimated_absorpt_T_max   0.882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6253
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7461
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.079
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.883
_diffrn_reflns_point_group_measured_fraction_full 0.884
_reflns_number_total             4346
_reflns_number_gt                3881
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.634
_reflns_Friedel_fraction_max     0.746
_reflns_Friedel_fraction_full    0.749

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0429P)²] 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 1358 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.023(12)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4346
_refine_ls_number_parameters     334
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.0890
_refine_ls_wR_factor_gt          0.0866
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.008 0.024 0.666 33 12 ' '
2 -0.009 0.524 0.334 33 12 ' '
_platon_squeeze_details          
;
;



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 0.88466(5) 0.57971(8) 0.71313(3) 0.04130(18) Uani 1 1 d . . . . .
Cl1 Cl 0.34553(11) 1.0744(3) 0.72050(8) 0.0617(4) Uani 1 1 d . . . . .
Cl2 Cl 0.45615(13) 0.5444(3) 0.93078(12) 0.0925(7) Uani 1 1 d . . . . .
Cl3 Cl 0.69690(14) 0.6171(3) 1.06192(9) 0.0792(6) Uani 1 1 d . . . . .
N1 N 0.7913(3) 0.6786(5) 0.6165(2) 0.0348(9) Uani 1 1 d . . . . .
N2 N 0.8390(3) 0.7440(5) 0.7864(2) 0.0371(9) Uani 1 1 d . . . . .
N3 N 0.9990(4) 0.4887(7) 0.8107(3) 0.0579(13) Uani 1 1 d . . . . .
O1 O 0.9327(4) 0.3545(6) 0.5049(2) 0.0632(11) Uani 1 1 d . . . . .
O2 O 0.9286(4) 0.4072(6) 0.6408(2) 0.0607(11) Uani 1 1 d . . . . .
O3 O 0.9175(3) 0.8805(6) 0.9140(2) 0.0650(11) Uani 1 1 d . . . . .
C1 C 0.9025(5) 0.4462(8) 0.5605(3) 0.0484(13) Uani 1 1 d . . . . .
C2 C 0.8323(4) 0.6121(7) 0.5396(3) 0.0419(12) Uani 1 1 d . . . . .
H2A H 0.8841 0.6990 0.5188 0.050 Uiso 1 1 calc R U . . .
H2B H 0.7615 0.5904 0.4951 0.050 Uiso 1 1 calc R U . . .
C3 C 0.7107(4) 0.8007(6) 0.6115(2) 0.0317(10) Uani 1 1 d . . . . .
C4 C 0.6644(4) 0.8615(6) 0.6869(3) 0.0325(9) Uani 1 1 d . . . . .
C5 C 0.5490(4) 0.9436(6) 0.6736(3) 0.0362(10) Uani 1 1 d . . . . .
H5 H 0.5103 0.9708 0.6184 0.043 Uiso 1 1 calc R U . . .
C6 C 0.4927(4) 0.9842(7) 0.7401(3) 0.0420(11) Uani 1 1 d . . . . .
C7 C 0.5507(4) 0.9532(7) 0.8224(3) 0.0430(11) Uani 1 1 d . . . . .
H7 H 0.5115 0.9810 0.8676 0.052 Uiso 1 1 calc R U . . .
C8 C 0.6670(4) 0.8810(7) 0.8378(3) 0.0381(11) Uani 1 1 d . . . . .
H8 H 0.7071 0.8659 0.8938 0.046 Uiso 1 1 calc R U . . .
C9 C 0.7263(4) 0.8298(6) 0.7711(3) 0.0336(10) Uani 1 1 d . . . . .
C10 C 0.9213(5) 0.7687(8) 0.8596(3) 0.0476(13) Uani 1 1 d . . . . .
C11 C 1.0278(5) 0.6461(9) 0.8682(3) 0.0605(18) Uani 1 1 d . . . . .
H11 H 1.0501 0.6070 0.9275 0.073 Uiso 1 1 calc R U . . .
C12 C 1.1398(5) 0.7361(14) 0.8405(4) 0.093(3) Uani 1 1 d . . . . .
H12A H 1.1185 0.8541 0.8199 0.111 Uiso 1 1 calc R U . . .
H12B H 1.2080 0.7433 0.8881 0.111 Uiso 1 1 calc R U . . .
C13 C 1.1746(6) 0.6240(16) 0.7701(4) 0.100(3) Uani 1 1 d . . . . .
H13A H 1.1371 0.6675 0.7143 0.120 Uiso 1 1 calc R U . . .
H13B H 1.2632 0.6188 0.7738 0.120 Uiso 1 1 calc R U . . .
C14 C 1.1230(6) 0.4477(14) 0.7880(4) 0.092(3) Uani 1 1 d . . . . .
H14A H 1.1760 0.3897 0.8350 0.111 Uiso 1 1 calc R U . . .
H14B H 1.1141 0.3725 0.7381 0.111 Uiso 1 1 calc R U . . .
C15 C 0.9481(7) 0.3383(10) 0.8520(4) 0.074(2) Uani 1 1 d . . . . .
H15A H 1.0054 0.3067 0.9033 0.089 Uiso 1 1 calc R U . . .
H15B H 0.9404 0.2381 0.8138 0.089 Uiso 1 1 calc R U . . .
C16 C 0.8245(6) 0.3766(8) 0.8750(3) 0.0557(14) Uani 1 1 d . . . . .
C17 C 0.7165(7) 0.3403(8) 0.8183(4) 0.0675(18) Uani 1 1 d . . . . .
H17 H 0.7203 0.2820 0.7676 0.081 Uiso 1 1 calc R U . . .
C18 C 0.6060(7) 0.3886(9) 0.8358(4) 0.0688(18) Uani 1 1 d . . . . .
H18 H 0.5348 0.3643 0.7967 0.083 Uiso 1 1 calc R U . . .
C19 C 0.5975(5) 0.4737(8) 0.9111(3) 0.0562(14) Uani 1 1 d . . . . .
C20 C 0.7040(5) 0.5059(8) 0.9682(3) 0.0528(13) Uani 1 1 d . . . . .
C21 C 0.8154(5) 0.4560(7) 0.9512(3) 0.0519(13) Uani 1 1 d . . . . .
H21 H 0.8862 0.4757 0.9915 0.062 Uiso 1 1 calc R U . . .
C22 C 0.6612(4) 0.8829(6) 0.5272(3) 0.0337(10) Uani 1 1 d . . . . .
C23 C 0.7267(4) 1.0179(7) 0.4978(3) 0.0469(13) Uani 1 1 d . . . . .
H23 H 0.7993 1.0578 0.5311 0.056 Uiso 1 1 calc R U . . .
C24 C 0.6847(5) 1.0936(9) 0.4192(3) 0.0540(13) Uani 1 1 d . . . . .
H24 H 0.7295 1.1828 0.3991 0.065 Uiso 1 1 calc R U . . .
C25 C 0.5757(5) 1.0357(7) 0.3708(3) 0.0550(15) Uani 1 1 d . . . . .
H25 H 0.5468 1.0874 0.3181 0.066 Uiso 1 1 calc R U . . .
C26 C 0.5106(5) 0.9046(8) 0.3990(3) 0.0512(13) Uani 1 1 d . . . . .
H26 H 0.4372 0.8670 0.3657 0.061 Uiso 1 1 calc R U . . .
C27 C 0.5529(4) 0.8257(7) 0.4776(3) 0.0450(12) Uani 1 1 d . . . . .
H27 H 0.5084 0.7349 0.4966 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 N2 1.843(4) . ?
Ni1 N1 1.853(3) . ?
Ni1 O2 1.868(4) . ?
Ni1 N3 1.946(4) . ?
Cl1 C6 1.740(5) . ?
Cl2 C19 1.732(6) . ?
Cl3 C20 1.732(6) . ?
N1 C3 1.279(5) . ?
N1 C2 1.472(5) . ?
N2 C10 1.357(6) . ?
N2 C9 1.387(6) . ?
N3 C15 1.480(9) . ?
N3 C11 1.506(8) . ?
N3 C14 1.511(7) . ?
O1 C1 1.220(6) . ?
O2 C1 1.296(6) . ?
O3 C10 1.222(7) . ?
C1 C2 1.487(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.464(6) . ?
C3 C22 1.495(6) . ?
C4 C5 1.401(6) . ?
C4 C9 1.413(6) . ?
C5 C6 1.358(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.373(6) . ?
C7 C8 1.378(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.401(6) . ?
C8 H8 0.9300 . ?
C10 C11 1.487(8) . ?
C11 C12 1.546(9) . ?
C11 H11 0.9800 . ?
C12 C13 1.514(10) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.504(13) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.504(8) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C21 1.377(7) . ?
C16 C17 1.389(8) . ?
C17 C18 1.350(9) . ?
C17 H17 0.9300 . ?
C18 C19 1.382(9) . ?
C18 H18 0.9300 . ?
C19 C20 1.374(7) . ?
C20 C21 1.360(7) . ?
C21 H21 0.9300 . ?
C22 C27 1.380(6) . ?
C22 C23 1.385(7) . ?
C23 C24 1.382(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.379(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.353(8) . ?
C25 H25 0.9300 . ?
C26 C27 1.392(6) . ?
C26 H26 0.9300 . ?
C27 H27 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
N2 Ni1 N1 94.47(16) . . ?
N2 Ni1 O2 178.05(19) . . ?
N1 Ni1 O2 86.50(15) . . ?
N2 Ni1 N3 86.88(17) . . ?
N1 Ni1 N3 173.4(2) . . ?
O2 Ni1 N3 92.35(17) . . ?
C3 N1 C2 120.8(3) . . ?
C3 N1 Ni1 128.6(3) . . ?
C2 N1 Ni1 110.2(3) . . ?
C10 N2 C9 121.9(4) . . ?
C10 N2 Ni1 114.9(3) . . ?
C9 N2 Ni1 123.1(3) . . ?
C15 N3 C11 113.5(4) . . ?
C15 N3 C14 112.3(6) . . ?
C11 N3 C14 102.0(5) . . ?
C15 N3 Ni1 112.8(4) . . ?
C11 N3 Ni1 103.9(3) . . ?
C14 N3 Ni1 111.5(3) . . ?
C1 O2 Ni1 114.4(3) . . ?
O1 C1 O2 123.1(5) . . ?
O1 C1 C2 121.4(4) . . ?
O2 C1 C2 115.5(4) . . ?
N1 C2 C1 109.3(4) . . ?
N1 C2 H2A 109.8 . . ?
C1 C2 H2A 109.8 . . ?
N1 C2 H2B 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.3 . . ?
N1 C3 C4 121.3(4) . . ?
N1 C3 C22 119.8(4) . . ?
C4 C3 C22 118.9(4) . . ?
C5 C4 C9 119.5(4) . . ?
C5 C4 C3 117.3(4) . . ?
C9 C4 C3 123.1(4) . . ?
C6 C5 C4 120.9(4) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 120.5(4) . . ?
C5 C6 Cl1 119.5(3) . . ?
C7 C6 Cl1 120.0(3) . . ?
C6 C7 C8 119.9(4) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C7 C8 C9 121.6(4) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
N2 C9 C8 121.6(4) . . ?
N2 C9 C4 120.9(4) . . ?
C8 C9 C4 117.5(4) . . ?
O3 C10 N2 127.1(5) . . ?
O3 C10 C11 119.9(5) . . ?
N2 C10 C11 112.9(5) . . ?
C10 C11 N3 111.3(4) . . ?
C10 C11 C12 110.9(6) . . ?
N3 C11 C12 105.6(5) . . ?
C10 C11 H11 109.6 . . ?
N3 C11 H11 109.6 . . ?
C12 C11 H11 109.6 . . ?
C13 C12 C11 106.6(7) . . ?
C13 C12 H12A 110.4 . . ?
C11 C12 H12A 110.4 . . ?
C13 C12 H12B 110.4 . . ?
C11 C12 H12B 110.4 . . ?
H12A C12 H12B 108.6 . . ?
C14 C13 C12 101.9(6) . . ?
C14 C13 H13A 111.4 . . ?
C12 C13 H13A 111.4 . . ?
C14 C13 H13B 111.4 . . ?
C12 C13 H13B 111.4 . . ?
H13A C13 H13B 109.3 . . ?
C13 C14 N3 104.6(6) . . ?
C13 C14 H14A 110.8 . . ?
N3 C14 H14A 110.8 . . ?
C13 C14 H14B 110.8 . . ?
N3 C14 H14B 110.8 . . ?
H14A C14 H14B 108.9 . . ?
N3 C15 C16 113.1(5) . . ?
N3 C15 H15A 109.0 . . ?
C16 C15 H15A 109.0 . . ?
N3 C15 H15B 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C21 C16 C17 118.1(6) . . ?
C21 C16 C15 120.9(5) . . ?
C17 C16 C15 120.9(6) . . ?
C18 C17 C16 120.9(6) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 120.8(5) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C20 C19 C18 118.4(6) . . ?
C20 C19 Cl2 121.1(5) . . ?
C18 C19 Cl2 120.5(4) . . ?
C21 C20 C19 121.0(5) . . ?
C21 C20 Cl3 119.4(4) . . ?
C19 C20 Cl3 119.5(5) . . ?
C20 C21 C16 120.7(5) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?
C27 C22 C23 119.4(4) . . ?
C27 C22 C3 121.5(4) . . ?
C23 C22 C3 119.1(4) . . ?
C24 C23 C22 120.4(5) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C25 C24 C23 119.5(5) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C26 C25 C24 120.7(5) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C25 C26 C27 120.3(5) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C22 C27 C26 119.8(5) . . ?
C22 C27 H27 120.1 . . ?
C26 C27 H27 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 Ni1 N1 C3 -9.7(4) . . . . ?
O2 Ni1 N1 C3 168.6(4) . . . . ?
N2 Ni1 N1 C2 163.2(3) . . . . ?
O2 Ni1 N1 C2 -18.5(3) . . . . ?
N1 Ni1 N2 C10 -154.0(4) . . . . ?
N3 Ni1 N2 C10 19.5(4) . . . . ?
N1 Ni1 N2 C9 29.4(4) . . . . ?
N3 Ni1 N2 C9 -157.0(4) . . . . ?
N1 Ni1 O2 C1 14.0(4) . . . . ?
N3 Ni1 O2 C1 -159.5(4) . . . . ?
Ni1 O2 C1 O1 174.5(4) . . . . ?
Ni1 O2 C1 C2 -5.4(6) . . . . ?
C3 N1 C2 C1 -167.0(4) . . . . ?
Ni1 N1 C2 C1 19.5(5) . . . . ?
O1 C1 C2 N1 170.7(5) . . . . ?
O2 C1 C2 N1 -9.4(6) . . . . ?
C2 N1 C3 C4 176.7(4) . . . . ?
Ni1 N1 C3 C4 -11.0(6) . . . . ?
C2 N1 C3 C22 -2.7(6) . . . . ?
Ni1 N1 C3 C22 169.5(3) . . . . ?
N1 C3 C4 C5 -157.1(4) . . . . ?
C22 C3 C4 C5 22.4(6) . . . . ?
N1 C3 C4 C9 18.3(7) . . . . ?
C22 C3 C4 C9 -162.2(4) . . . . ?
C9 C4 C5 C6 -3.8(7) . . . . ?
C3 C4 C5 C6 171.8(4) . . . . ?
C4 C5 C6 C7 3.2(8) . . . . ?
C4 C5 C6 Cl1 -176.2(4) . . . . ?
C5 C6 C7 C8 0.2(8) . . . . ?
Cl1 C6 C7 C8 179.7(4) . . . . ?
C6 C7 C8 C9 -3.1(8) . . . . ?
C10 N2 C9 C8 -28.6(7) . . . . ?
Ni1 N2 C9 C8 147.7(4) . . . . ?
C10 N2 C9 C4 154.3(5) . . . . ?
Ni1 N2 C9 C4 -29.3(6) . . . . ?
C7 C8 C9 N2 -174.6(5) . . . . ?
C7 C8 C9 C4 2.5(7) . . . . ?
C5 C4 C9 N2 178.0(4) . . . . ?
C3 C4 C9 N2 2.8(7) . . . . ?
C5 C4 C9 C8 0.9(6) . . . . ?
C3 C4 C9 C8 -174.4(4) . . . . ?
C9 N2 C10 O3 -10.6(8) . . . . ?
Ni1 N2 C10 O3 172.7(5) . . . . ?
C9 N2 C10 C11 172.0(4) . . . . ?
Ni1 N2 C10 C11 -4.6(6) . . . . ?
O3 C10 C11 N3 163.4(5) . . . . ?
N2 C10 C11 N3 -19.1(7) . . . . ?
O3 C10 C11 C12 -79.3(6) . . . . ?
N2 C10 C11 C12 98.2(6) . . . . ?
C15 N3 C11 C10 -91.6(5) . . . . ?
C14 N3 C11 C10 147.3(5) . . . . ?
Ni1 N3 C11 C10 31.3(5) . . . . ?
C15 N3 C11 C12 148.0(5) . . . . ?
C14 N3 C11 C12 26.9(6) . . . . ?
Ni1 N3 C11 C12 -89.1(5) . . . . ?
C10 C11 C12 C13 -122.7(6) . . . . ?
N3 C11 C12 C13 -2.0(7) . . . . ?
C11 C12 C13 C14 -23.9(7) . . . . ?
C12 C13 C14 N3 41.6(6) . . . . ?
C15 N3 C14 C13 -165.0(5) . . . . ?
C11 N3 C14 C13 -43.1(5) . . . . ?
Ni1 N3 C14 C13 67.3(6) . . . . ?
C11 N3 C15 C16 65.0(6) . . . . ?
C14 N3 C15 C16 -179.9(5) . . . . ?
Ni1 N3 C15 C16 -52.9(6) . . . . ?
N3 C15 C16 C21 -86.1(6) . . . . ?
N3 C15 C16 C17 90.9(7) . . . . ?
C21 C16 C17 C18 2.9(9) . . . . ?
C15 C16 C17 C18 -174.2(6) . . . . ?
C16 C17 C18 C19 -0.7(9) . . . . ?
C17 C18 C19 C20 -0.8(9) . . . . ?
C17 C18 C19 Cl2 177.0(5) . . . . ?
C18 C19 C20 C21 0.2(8) . . . . ?
Cl2 C19 C20 C21 -177.6(4) . . . . ?
C18 C19 C20 Cl3 178.4(4) . . . . ?
Cl2 C19 C20 Cl3 0.6(7) . . . . ?
C19 C20 C21 C16 2.0(9) . . . . ?
Cl3 C20 C21 C16 -176.2(4) . . . . ?
C17 C16 C21 C20 -3.5(8) . . . . ?
C15 C16 C21 C20 173.5(5) . . . . ?
N1 C3 C22 C27 95.3(5) . . . . ?
C4 C3 C22 C27 -84.1(6) . . . . ?
N1 C3 C22 C23 -83.8(6) . . . . ?
C4 C3 C22 C23 96.8(5) . . . . ?
C27 C22 C23 C24 -0.6(7) . . . . ?
C3 C22 C23 C24 178.5(5) . . . . ?
C22 C23 C24 C25 1.1(8) . . . . ?
C23 C24 C25 C26 -0.8(8) . . . . ?
C24 C25 C26 C27 -0.1(8) . . . . ?
C23 C22 C27 C26 -0.3(7) . . . . ?
C3 C22 C27 C26 -179.4(4) . . . . ?
C25 C26 C27 C22 0.6(8) . . . . ?

_refine_diff_density_max         0.422
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.055

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_cd16563
_database_code_depnum_ccdc_archive 'CCDC 1520063'
_audit_update_record             
;
2016-11-30 deposited with the CCDC.
2017-03-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H27 N3 Ni O3'
_chemical_formula_weight         512.23

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.7857(8)
_cell_length_b                   9.8844(8)
_cell_length_c                   25.741(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2489.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3573
_cell_measurement_theta_min      4.453
_cell_measurement_theta_max      47.320

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.814
_shelx_estimated_absorpt_T_min   0.854
_shelx_estimated_absorpt_T_max   0.902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6469
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14407
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.207
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_full        25.242
_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             4626
_reflns_number_gt                3962
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_max     1.000
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0767P)²+0.6009P] 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 1491 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.005(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4626
_refine_ls_number_parameters     305
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1348
_refine_ls_wR_factor_gt          0.1286
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.12754(8) 0.85286(6) 0.89895(2) 0.0490(2) Uani 1 1 d . . . . .
O1 O 0.1462(7) 0.6390(5) 1.02391(19) 0.104(2) Uani 1 1 d . . . . .
O2 O 0.1424(6) 0.7003(4) 0.94098(16) 0.0811(16) Uani 1 1 d . . . . .
O3 O -0.0131(5) 1.0666(5) 0.78402(17) 0.0712(13) Uani 1 1 d . . . . .
N1 N 0.1789(4) 0.9523(4) 0.95675(16) 0.0425(10) Uani 1 1 d . . . . .
N2 N 0.1150(4) 1.0015(4) 0.85560(14) 0.0401(9) Uani 1 1 d . . . . .
N3 N 0.0723(6) 0.7444(5) 0.83959(19) 0.0670(15) Uani 1 1 d . . . . .
C1 C 0.1478(8) 0.7248(6) 0.9900(2) 0.0702(19) Uani 1 1 d . . . . .
C2 C 0.1512(7) 0.8742(6) 1.0045(2) 0.0572(15) Uani 1 1 d . . . . .
H2 H 0.2245 0.8901 1.0297 0.069 Uiso 1 1 calc R U . . .
C3 C 0.2296(5) 1.0717(5) 0.95756(19) 0.0396(11) Uani 1 1 d . . . . .
C4 C 0.2482(5) 1.1537(5) 0.91055(19) 0.0437(11) Uani 1 1 d . . . . .
C5 C 0.3271(7) 1.2706(6) 0.9142(2) 0.0652(17) Uani 1 1 d . . . . .
H5 H 0.3655 1.2930 0.9461 0.078 Uiso 1 1 calc R U . . .
C6 C 0.3501(8) 1.3534(8) 0.8728(3) 0.086(2) Uani 1 1 d . . . . .
H6 H 0.4050 1.4297 0.8761 0.103 Uiso 1 1 calc R U . . .
C7 C 0.2909(9) 1.3221(8) 0.8263(3) 0.087(2) Uani 1 1 d . . . . .
H7 H 0.3033 1.3792 0.7979 0.104 Uiso 1 1 calc R U . . .
C8 C 0.2137(7) 1.2076(6) 0.8209(2) 0.0608(16) Uani 1 1 d . . . . .
H8 H 0.1767 1.1877 0.7885 0.073 Uiso 1 1 calc R U . . .
C9 C 0.1884(5) 1.1196(5) 0.8621(2) 0.0428(12) Uani 1 1 d . . . . .
C10 C 0.0312(5) 0.9817(6) 0.8137(2) 0.0464(12) Uani 1 1 d . . . . .
C11 C -0.0145(5) 0.8374(6) 0.8075(2) 0.0525(13) Uani 1 1 d . . . . .
H11 H -0.0075 0.8114 0.7708 0.063 Uiso 1 1 calc R U . . .
C12 C -0.1620(7) 0.8172(11) 0.8259(3) 0.099(3) Uani 1 1 d . . . . .
H12A H -0.2215 0.7927 0.7973 0.119 Uiso 1 1 calc R U . . .
H12B H -0.1970 0.8982 0.8425 0.119 Uiso 1 1 calc R U . . .
C13 C -0.1486(13) 0.6988(13) 0.8657(3) 0.134(5) Uani 1 1 d . . . . .
H13A H -0.1474 0.7327 0.9010 0.161 Uiso 1 1 calc R U . . .
H13B H -0.2239 0.6356 0.8620 0.161 Uiso 1 1 calc R U . . .
C14 C -0.0170(13) 0.6333(9) 0.8524(3) 0.117(4) Uani 1 1 d . . . . .
H14A H 0.0183 0.5824 0.8817 0.140 Uiso 1 1 calc R U . . .
H14B H -0.0275 0.5727 0.8230 0.140 Uiso 1 1 calc R U . . .
C15 C 0.1998(10) 0.6929(8) 0.8121(3) 0.095(3) Uani 1 1 d . . . . .
H15A H 0.2429 0.6261 0.8343 0.114 Uiso 1 1 calc R U . . .
H15B H 0.1713 0.6468 0.7807 0.114 Uiso 1 1 calc R U . . .
C16 C 0.3001(6) 0.7910(7) 0.7983(4) 0.129(3) Uani 1 1 d G U . . .
C17 C 0.3947(8) 0.8310(8) 0.8355(3) 0.140(3) Uani 1 1 d G U . . .
H17 H 0.3962 0.7889 0.8678 0.168 Uiso 1 1 calc R U . . .
C18 C 0.4872(7) 0.9337(9) 0.8244(4) 0.158(3) Uani 1 1 d G U . . .
H18 H 0.5506 0.9604 0.8494 0.189 Uiso 1 1 calc R U . . .
C19 C 0.4851(7) 0.9965(7) 0.7761(5) 0.162(3) Uani 1 1 d G U . . .
H19 H 0.5470 1.0652 0.7687 0.195 Uiso 1 1 calc R U . . .
C20 C 0.3905(9) 0.9565(9) 0.7389(3) 0.163(3) Uani 1 1 d G U . . .
H20 H 0.3890 0.9986 0.7066 0.196 Uiso 1 1 calc R U . . .
C21 C 0.2980(7) 0.8538(10) 0.7500(3) 0.147(3) Uani 1 1 d G U . . .
H21 H 0.2346 0.8271 0.7251 0.176 Uiso 1 1 calc R U . . .
C22 C 0.2710(5) 1.1342(5) 1.0087(2) 0.0452(12) Uani 1 1 d . . . . .
C23 C 0.1928(8) 1.2371(8) 1.0295(3) 0.077(2) Uani 1 1 d . . . . .
H23 H 0.1124 1.2636 1.0131 0.093 Uiso 1 1 calc R U . . .
C24 C 0.2340(9) 1.3006(10) 1.0746(3) 0.098(3) Uani 1 1 d . . . . .
H24 H 0.1804 1.3690 1.0886 0.118 Uiso 1 1 calc R U . . .
C25 C 0.3524(8) 1.2642(7) 1.0987(3) 0.082(2) Uani 1 1 d . . . . .
H25 H 0.3794 1.3074 1.1291 0.098 Uiso 1 1 calc R U . . .
C26 C 0.4313(7) 1.1634(7) 1.0777(3) 0.0688(19) Uani 1 1 d . . . . .
H26 H 0.5123 1.1387 1.0941 0.083 Uiso 1 1 calc R U . . .
C27 C 0.3924(6) 1.0981(5) 1.0327(2) 0.0529(13) Uani 1 1 d . . . . .
H27 H 0.4470 1.0304 1.0187 0.063 Uiso 1 1 calc R U . . .
C28 C 0.0155(10) 0.9172(9) 1.0278(3) 0.106(3) Uani 1 1 d . . . . .
H28A H 0.0228 1.0080 1.0407 0.160 Uiso 1 1 calc R U . . .
H28B H -0.0081 0.8574 1.0557 0.160 Uiso 1 1 calc R U . . .
H28C H -0.0542 0.9135 1.0016 0.160 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 N2 1.849(4) . ?
Ni1 N1 1.852(4) . ?
Ni1 O2 1.862(4) . ?
Ni1 N3 1.943(5) . ?
O1 C1 1.217(7) . ?
O2 C1 1.286(7) . ?
O3 C10 1.215(7) . ?
N1 C3 1.281(7) . ?
N1 C2 1.476(7) . ?
N2 C10 1.369(6) . ?
N2 C9 1.381(6) . ?
N3 C14 1.441(10) . ?
N3 C11 1.500(8) . ?
N3 C15 1.522(10) . ?
C1 C2 1.523(8) . ?
C2 C28 1.518(11) . ?
C2 H2 0.9800 . ?
C3 C4 1.467(7) . ?
C3 C22 1.509(7) . ?
C4 C5 1.393(8) . ?
C4 C9 1.418(7) . ?
C5 C6 1.363(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.365(11) . ?
C6 H6 0.9300 . ?
C7 C8 1.367(10) . ?
C7 H7 0.9300 . ?
C8 C9 1.394(8) . ?
C8 H8 0.9300 . ?
C10 C11 1.504(8) . ?
C11 C12 1.533(9) . ?
C11 H11 0.9800 . ?
C12 C13 1.559(14) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.482(16) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.425(11) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.3900 . ?
C16 C21 1.3900 . ?
C17 C18 1.3900 . ?
C17 H17 0.9300 . ?
C18 C19 1.3900 . ?
C18 H18 0.9300 . ?
C19 C20 1.3900 . ?
C19 H19 0.9300 . ?
C20 C21 1.3900 . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.381(8) . ?
C22 C27 1.386(8) . ?
C23 C24 1.380(9) . ?
C23 H23 0.9300 . ?
C24 C25 1.363(11) . ?
C24 H24 0.9300 . ?
C25 C26 1.372(10) . ?
C25 H25 0.9300 . ?
C26 C27 1.380(8) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 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
N2 Ni1 N1 94.66(17) . . ?
N2 Ni1 O2 178.3(2) . . ?
N1 Ni1 O2 86.67(19) . . ?
N2 Ni1 N3 86.87(19) . . ?
N1 Ni1 N3 178.4(2) . . ?
O2 Ni1 N3 91.81(19) . . ?
C1 O2 Ni1 114.9(4) . . ?
C3 N1 C2 122.6(4) . . ?
C3 N1 Ni1 127.4(4) . . ?
C2 N1 Ni1 110.0(3) . . ?
C10 N2 C9 121.9(4) . . ?
C10 N2 Ni1 113.7(3) . . ?
C9 N2 Ni1 124.4(3) . . ?
C14 N3 C11 104.5(6) . . ?
C14 N3 C15 110.4(7) . . ?
C11 N3 C15 114.4(5) . . ?
C14 N3 Ni1 114.2(5) . . ?
C11 N3 Ni1 104.6(4) . . ?
C15 N3 Ni1 108.8(4) . . ?
O1 C1 O2 124.8(6) . . ?
O1 C1 C2 120.0(6) . . ?
O2 C1 C2 115.1(5) . . ?
N1 C2 C28 110.0(5) . . ?
N1 C2 C1 107.9(5) . . ?
C28 C2 C1 110.4(6) . . ?
N1 C2 H2 109.5 . . ?
C28 C2 H2 109.5 . . ?
C1 C2 H2 109.5 . . ?
N1 C3 C4 122.9(4) . . ?
N1 C3 C22 119.7(5) . . ?
C4 C3 C22 117.4(4) . . ?
C5 C4 C9 119.0(5) . . ?
C5 C4 C3 118.1(5) . . ?
C9 C4 C3 122.9(5) . . ?
C6 C5 C4 122.5(6) . . ?
C6 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
C7 C6 C5 118.7(6) . . ?
C7 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C6 C7 C8 120.7(7) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C7 C8 C9 122.5(6) . . ?
C7 C8 H8 118.7 . . ?
C9 C8 H8 118.7 . . ?
N2 C9 C8 121.9(5) . . ?
N2 C9 C4 121.4(4) . . ?
C8 C9 C4 116.6(5) . . ?
O3 C10 N2 127.6(5) . . ?
O3 C10 C11 118.8(5) . . ?
N2 C10 C11 113.4(4) . . ?
N3 C11 C10 110.7(4) . . ?
N3 C11 C12 106.4(6) . . ?
C10 C11 C12 111.8(6) . . ?
N3 C11 H11 109.3 . . ?
C10 C11 H11 109.3 . . ?
C12 C11 H11 109.3 . . ?
C11 C12 C13 102.8(7) . . ?
C11 C12 H12A 111.2 . . ?
C13 C12 H12A 111.2 . . ?
C11 C12 H12B 111.2 . . ?
C13 C12 H12B 111.2 . . ?
H12A C12 H12B 109.1 . . ?
C14 C13 C12 104.5(7) . . ?
C14 C13 H13A 110.9 . . ?
C12 C13 H13A 110.9 . . ?
C14 C13 H13B 110.9 . . ?
C12 C13 H13B 110.9 . . ?
H13A C13 H13B 108.9 . . ?
N3 C14 C13 104.3(8) . . ?
N3 C14 H14A 110.9 . . ?
C13 C14 H14A 110.9 . . ?
N3 C14 H14B 110.9 . . ?
C13 C14 H14B 110.9 . . ?
H14A C14 H14B 108.9 . . ?
C16 C15 N3 117.0(5) . . ?
C16 C15 H15A 108.1 . . ?
N3 C15 H15A 108.1 . . ?
C16 C15 H15B 108.1 . . ?
N3 C15 H15B 108.1 . . ?
H15A C15 H15B 107.3 . . ?
C17 C16 C21 120.0 . . ?
C17 C16 C15 118.7(7) . . ?
C21 C16 C15 121.1(7) . . ?
C16 C17 C18 120.0 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 120.0 . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C20 C19 C18 120.0 . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 120.0 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C16 120.0 . . ?
C20 C21 H21 120.0 . . ?
C16 C21 H21 120.0 . . ?
C23 C22 C27 119.4(5) . . ?
C23 C22 C3 119.4(5) . . ?
C27 C22 C3 121.0(5) . . ?
C24 C23 C22 119.9(7) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C25 C24 C23 120.8(8) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C24 C25 C26 119.4(6) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
C25 C26 C27 121.0(6) . . ?
C25 C26 H26 119.5 . . ?
C27 C26 H26 119.5 . . ?
C26 C27 C22 119.4(6) . . ?
C26 C27 H27 120.3 . . ?
C22 C27 H27 120.3 . . ?
C2 C28 H28A 109.5 . . ?
C2 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C2 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Ni1 O2 C1 15.0(6) . . . . ?
N3 Ni1 O2 C1 -164.5(6) . . . . ?
N2 Ni1 N1 C3 -19.6(5) . . . . ?
O2 Ni1 N1 C3 159.4(5) . . . . ?
N2 Ni1 N1 C2 159.6(4) . . . . ?
O2 Ni1 N1 C2 -21.5(4) . . . . ?
N1 Ni1 N2 C10 -156.7(3) . . . . ?
N3 Ni1 N2 C10 22.8(4) . . . . ?
N1 Ni1 N2 C9 27.1(4) . . . . ?
N3 Ni1 N2 C9 -153.4(4) . . . . ?
Ni1 O2 C1 O1 173.6(7) . . . . ?
Ni1 O2 C1 C2 -4.1(9) . . . . ?
C3 N1 C2 C28 82.0(7) . . . . ?
Ni1 N1 C2 C28 -97.2(6) . . . . ?
C3 N1 C2 C1 -157.5(5) . . . . ?
Ni1 N1 C2 C1 23.3(6) . . . . ?
O1 C1 C2 N1 169.4(7) . . . . ?
O2 C1 C2 N1 -12.7(9) . . . . ?
O1 C1 C2 C28 -70.3(9) . . . . ?
O2 C1 C2 C28 107.6(8) . . . . ?
C2 N1 C3 C4 -175.5(5) . . . . ?
Ni1 N1 C3 C4 3.6(7) . . . . ?
C2 N1 C3 C22 3.6(8) . . . . ?
Ni1 N1 C3 C22 -177.3(4) . . . . ?
N1 C3 C4 C5 -168.1(5) . . . . ?
C22 C3 C4 C5 12.8(7) . . . . ?
N1 C3 C4 C9 12.6(8) . . . . ?
C22 C3 C4 C9 -166.5(5) . . . . ?
C9 C4 C5 C6 -0.6(10) . . . . ?
C3 C4 C5 C6 -179.9(6) . . . . ?
C4 C5 C6 C7 1.5(12) . . . . ?
C5 C6 C7 C8 -2.1(13) . . . . ?
C6 C7 C8 C9 1.7(12) . . . . ?
C10 N2 C9 C8 -18.9(8) . . . . ?
Ni1 N2 C9 C8 157.0(4) . . . . ?
C10 N2 C9 C4 164.6(5) . . . . ?
Ni1 N2 C9 C4 -19.4(7) . . . . ?
C7 C8 C9 N2 -177.2(6) . . . . ?
C7 C8 C9 C4 -0.6(9) . . . . ?
C5 C4 C9 N2 176.7(5) . . . . ?
C3 C4 C9 N2 -4.1(8) . . . . ?
C5 C4 C9 C8 0.1(8) . . . . ?
C3 C4 C9 C8 179.4(5) . . . . ?
C9 N2 C10 O3 -16.6(8) . . . . ?
Ni1 N2 C10 O3 167.0(5) . . . . ?
C9 N2 C10 C11 167.2(4) . . . . ?
Ni1 N2 C10 C11 -9.1(5) . . . . ?
C14 N3 C11 C10 150.8(6) . . . . ?
C15 N3 C11 C10 -88.4(6) . . . . ?
Ni1 N3 C11 C10 30.5(5) . . . . ?
C14 N3 C11 C12 29.1(7) . . . . ?
C15 N3 C11 C12 149.9(6) . . . . ?
Ni1 N3 C11 C12 -91.1(5) . . . . ?
O3 C10 C11 N3 168.0(5) . . . . ?
N2 C10 C11 N3 -15.5(6) . . . . ?
O3 C10 C11 C12 -73.6(7) . . . . ?
N2 C10 C11 C12 102.9(6) . . . . ?
N3 C11 C12 C13 -5.2(7) . . . . ?
C10 C11 C12 C13 -126.2(6) . . . . ?
C11 C12 C13 C14 -19.7(8) . . . . ?
C11 N3 C14 C13 -42.3(7) . . . . ?
C15 N3 C14 C13 -165.6(6) . . . . ?
Ni1 N3 C14 C13 71.4(7) . . . . ?
C12 C13 C14 N3 38.7(8) . . . . ?
C14 N3 C15 C16 -178.2(7) . . . . ?
C11 N3 C15 C16 64.4(8) . . . . ?
Ni1 N3 C15 C16 -52.2(8) . . . . ?
N3 C15 C16 C17 83.6(7) . . . . ?
N3 C15 C16 C21 -91.5(7) . . . . ?
C21 C16 C17 C18 0.0 . . . . ?
C15 C16 C17 C18 -175.2(6) . . . . ?
C16 C17 C18 C19 0.0 . . . . ?
C17 C18 C19 C20 0.0 . . . . ?
C18 C19 C20 C21 0.0 . . . . ?
C19 C20 C21 C16 0.0 . . . . ?
C17 C16 C21 C20 0.0 . . . . ?
C15 C16 C21 C20 175.0(6) . . . . ?
N1 C3 C22 C23 -107.5(7) . . . . ?
C4 C3 C22 C23 71.7(7) . . . . ?
N1 C3 C22 C27 78.1(7) . . . . ?
C4 C3 C22 C27 -102.7(6) . . . . ?
C27 C22 C23 C24 -1.7(11) . . . . ?
C3 C22 C23 C24 -176.1(7) . . . . ?
C22 C23 C24 C25 0.9(14) . . . . ?
C23 C24 C25 C26 0.1(13) . . . . ?
C24 C25 C26 C27 -0.2(11) . . . . ?
C25 C26 C27 C22 -0.6(9) . . . . ?
C23 C22 C27 C26 1.5(9) . . . . ?
C3 C22 C27 C26 175.9(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C15 H15B O3 0.97 2.41 3.319(8) 156.4 3_546
C14 H14A O2 0.97 2.27 2.841(10) 116.6 .
C8 H8 O3 0.93 2.21 2.787(8) 119.2 .

_refine_diff_density_max         0.566
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.061

_shelxl_version_number           2013-4

