# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2010



data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Ye, Jinxing'
_publ_contact_author_email       yejx@ecust.edu.cn

_publ_section_title              
;
Catalytic Asymmetric Michael Addition of \^I+-, \^I^2^-Unsaturated
Aldehydes with Ni(II) Complexes of the Schiff Base of Glycine
;
loop_
_publ_author_name
'Xiaoyan Luo'
'Yufeng Zhou'
'Pengfei Li'
'Jiabin Gao'
'Weimin Yue'
;
Xinmiao Liang
;
'Jinxing Ye'

# Attachment '- 7ai CIF.cif'

data_7ai
_database_code_depnum_ccdc_archive 'CCDC 772140'
#TrackingRef '- 7ai CIF.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H36 Cl3 N3 Ni O5'
_chemical_formula_weight         719.71

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   8.565(4)
_cell_length_b                   12.029(6)
_cell_length_c                   16.760(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.239(10)
_cell_angle_gamma                90.00
_cell_volume                     1726.3(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    3244
_cell_measurement_theta_min      4.675
_cell_measurement_theta_max      48.563

_exptl_crystal_description       prismatic
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      1.384
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             748
_exptl_absorpt_coefficient_mu    0.837
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8847
_exptl_absorpt_correction_T_max  0.9593
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9261
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_sigmaI/netI    0.1077
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.22
_diffrn_reflns_theta_max         26.00
_reflns_number_total             6621
_reflns_number_gt                4185
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1370P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6621
_refine_ls_number_parameters     410
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.1231
_refine_ls_R_factor_gt           0.0793
_refine_ls_wR_factor_ref         0.2399
_refine_ls_wR_factor_gt          0.2011
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.050
_refine_ls_shift/su_mean         0.003

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni Ni 0.36288(10) 0.84970(8) 0.75235(5) 0.0437(3) Uani 1 1 d . . .
N1 N 0.4920(8) 0.7149(6) 0.7465(4) 0.0513(17) Uani 1 1 d . . .
N2 N 0.5279(8) 0.9211(6) 0.7041(4) 0.0474(16) Uani 1 1 d . . .
N3 N 0.2469(7) 0.9781(5) 0.7636(4) 0.0410(15) Uani 1 1 d . . .
O1 O 0.8004(7) 0.9120(6) 0.7077(5) 0.0726(19) Uani 1 1 d . . .
O2 O 0.1950(7) 0.7758(5) 0.7977(4) 0.0546(15) Uani 1 1 d . . .
O3 O -0.0108(7) 0.8062(5) 0.8735(4) 0.0627(17) Uani 1 1 d . . .
O4 O 0.0316(12) 1.0768(8) 1.1094(5) 0.102(3) Uani 1 1 d D . .
H4 H -0.0489 1.1080 1.0943 0.153 Uiso 1 1 calc RD . .
O5 O 0.4950(6) 1.0998(5) 0.8658(4) 0.0574(15) Uani 1 1 d . . .
C1 C 0.4525(13) 0.6298(8) 0.8087(6) 0.067(3) Uani 1 1 d . . .
H1A H 0.3414 0.6144 0.8055 0.080 Uiso 1 1 calc R . .
H1B H 0.4762 0.6600 0.8612 0.080 Uiso 1 1 calc R . .
C2 C 0.5439(14) 0.5197(8) 0.7981(7) 0.080(3) Uani 1 1 d . . .
H2A H 0.6550 0.5336 0.8046 0.096 Uiso 1 1 calc R . .
H2B H 0.5135 0.4669 0.8386 0.096 Uiso 1 1 calc R . .
C3 C 0.5100(15) 0.4708(8) 0.7151(8) 0.089(4) Uani 1 1 d . . .
H3A H 0.5704 0.4034 0.7081 0.107 Uiso 1 1 calc R . .
H3B H 0.4001 0.4521 0.7096 0.107 Uiso 1 1 calc R . .
C4 C 0.5536(16) 0.5565(10) 0.6514(8) 0.094(4) Uani 1 1 d . . .
H4A H 0.5270 0.5277 0.5988 0.112 Uiso 1 1 calc R . .
H4B H 0.6653 0.5699 0.6539 0.112 Uiso 1 1 calc R . .
C5 C 0.4659(13) 0.6665(8) 0.6649(6) 0.060(3) Uani 1 1 d . . .
H5A H 0.4988 0.7203 0.6256 0.072 Uiso 1 1 calc R . .
H5B H 0.3549 0.6538 0.6564 0.072 Uiso 1 1 calc R . .
C6 C 0.6525(10) 0.7593(8) 0.7572(6) 0.058(2) Uani 1 1 d . . .
H6A H 0.7258 0.7085 0.7332 0.070 Uiso 1 1 calc R . .
H6B H 0.6782 0.7642 0.8137 0.070 Uiso 1 1 calc R . .
C7 C 0.6690(10) 0.8731(7) 0.7197(6) 0.053(2) Uani 1 1 d . . .
C8 C 0.5132(10) 1.0187(8) 0.6598(5) 0.046(2) Uani 1 1 d . . .
C9 C 0.6237(11) 1.0479(9) 0.6016(6) 0.063(2) Uani 1 1 d . . .
H9 H 0.7099 1.0023 0.5943 0.075 Uiso 1 1 calc R . .
C10 C 0.6067(13) 1.1420(9) 0.5557(6) 0.072(3) Uani 1 1 d . . .
H10 H 0.6788 1.1563 0.5163 0.087 Uiso 1 1 calc R . .
C11 C 0.4873(13) 1.2149(9) 0.5664(6) 0.072(3) Uani 1 1 d . . .
H11 H 0.4814 1.2802 0.5367 0.087 Uiso 1 1 calc R . .
C12 C 0.3734(12) 1.1905(8) 0.6225(5) 0.060(2) Uani 1 1 d . . .
H12 H 0.2900 1.2390 0.6289 0.072 Uiso 1 1 calc R . .
C13 C 0.3836(10) 1.0918(7) 0.6701(5) 0.050(2) Uani 1 1 d . . .
C14 C 0.2605(8) 1.0725(6) 0.7265(5) 0.0394(17) Uani 1 1 d . . .
C15 C 0.1511(10) 1.1678(7) 0.7429(5) 0.050(2) Uani 1 1 d . . .
C16 C 0.1982(11) 1.2581(7) 0.7916(6) 0.058(2) Uani 1 1 d . . .
H16 H 0.2975 1.2580 0.8152 0.069 Uiso 1 1 calc R . .
C17 C 0.0994(12) 1.3464(11) 0.8047(6) 0.075(2) Uani 1 1 d . . .
H17 H 0.1285 1.4037 0.8391 0.090 Uiso 1 1 calc R . .
C18 C -0.0477(11) 1.3475(12) 0.7644(7) 0.082(3) Uani 1 1 d . . .
H18 H -0.1146 1.4076 0.7709 0.098 Uiso 1 1 calc R . .
C19 C -0.0920(12) 1.2621(9) 0.7165(7) 0.071(3) Uani 1 1 d . . .
H19 H -0.1888 1.2651 0.6903 0.086 Uiso 1 1 calc R . .
C20 C 0.0036(10) 1.1693(8) 0.7052(6) 0.058(2) Uani 1 1 d . . .
H20 H -0.0300 1.1101 0.6735 0.069 Uiso 1 1 calc R . .
C21 C 0.1326(8) 0.9662(6) 0.8295(5) 0.0399(17) Uani 1 1 d . . .
H21 H 0.0365 1.0072 0.8163 0.048 Uiso 1 1 calc R . .
C22 C 0.0988(8) 0.8426(9) 0.8344(5) 0.0493(18) Uani 1 1 d . . .
C23 C 0.2066(8) 1.0107(6) 0.9091(4) 0.0399(17) Uani 1 1 d . . .
H23 H 0.2316 1.0889 0.8989 0.048 Uiso 1 1 calc R . .
C24 C 0.0879(10) 1.0127(8) 0.9765(5) 0.056(2) Uani 1 1 d . . .
H24A H -0.0093 1.0446 0.9564 0.067 Uiso 1 1 calc R . .
H24B H 0.0668 0.9371 0.9932 0.067 Uiso 1 1 calc R . .
C25 C 0.1433(15) 1.0766(13) 1.0449(8) 0.102(4) Uani 1 1 d . . .
H25A H 0.1626 1.1526 1.0284 0.122 Uiso 1 1 calc R . .
H25B H 0.2414 1.0456 1.0644 0.122 Uiso 1 1 calc R . .
C26 C 0.3610(9) 0.9562(7) 0.9313(5) 0.0464(19) Uani 1 1 d . . .
C27 C 0.3697(11) 0.8599(9) 0.9747(5) 0.061(2) Uani 1 1 d . . .
H27 H 0.2769 0.8258 0.9890 0.073 Uiso 1 1 calc R . .
C28 C 0.5141(13) 0.8085(8) 0.9995(6) 0.067(3) Uani 1 1 d . . .
H28 H 0.5160 0.7429 1.0289 0.080 Uiso 1 1 calc R . .
C29 C 0.6467(12) 0.8599(12) 0.9783(5) 0.074(3) Uani 1 1 d . . .
H29 H 0.7423 0.8293 0.9939 0.089 Uiso 1 1 calc R . .
C30 C 0.6446(11) 0.9561(9) 0.9341(6) 0.069(3) Uani 1 1 d . . .
H30 H 0.7381 0.9894 0.9201 0.083 Uiso 1 1 calc R . .
C31 C 0.5045(9) 1.0037(7) 0.9105(5) 0.050(2) Uani 1 1 d . . .
C32 C 0.6415(13) 1.1473(10) 0.8366(8) 0.083(3) Uani 1 1 d . . .
H32A H 0.7104 1.1631 0.8810 0.124 Uiso 1 1 calc R . .
H32B H 0.6193 1.2147 0.8079 0.124 Uiso 1 1 calc R . .
H32C H 0.6903 1.0950 0.8018 0.124 Uiso 1 1 calc R . .
Cl1 Cl 0.0438(17) 0.6207(13) 0.6329(9) 0.193(5) Uiso 1 1 d PD A 1
Cl2 Cl -0.02(5) 0.603(6) 0.486(7) 0.21(2) Uiso 1 1 d PD A 1
Cl3 Cl 0.1620(12) 0.8419(12) 0.5745(6) 0.174(3) Uiso 1 1 d PD A 1
C33 C 0.029(4) 0.726(3) 0.559(3) 0.20(2) Uiso 1 1 d PD A 1
H33 H -0.07(6) 0.76(5) 0.57(3) 0.243 Uiso 1 1 calc P B 1

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ni 0.0394(5) 0.0371(5) 0.0551(5) -0.0006(6) 0.0090(4) 0.0039(5)
N1 0.050(4) 0.046(4) 0.058(4) -0.009(3) 0.005(3) 0.006(3)
N2 0.034(3) 0.047(4) 0.062(4) -0.005(3) 0.011(3) 0.004(3)
N3 0.031(3) 0.040(4) 0.052(4) 0.000(3) 0.004(3) 0.000(3)
O1 0.038(3) 0.071(4) 0.109(5) -0.004(4) 0.009(3) 0.003(3)
O2 0.043(3) 0.035(3) 0.087(5) -0.005(3) 0.010(3) -0.002(3)
O3 0.052(4) 0.053(4) 0.084(4) 0.006(3) 0.013(3) -0.012(3)
O4 0.148(8) 0.068(5) 0.093(6) 0.000(5) 0.066(5) -0.003(6)
O5 0.039(3) 0.055(4) 0.079(4) 0.000(3) 0.014(3) -0.007(3)
C1 0.080(7) 0.046(5) 0.074(7) 0.012(5) 0.012(5) 0.014(5)
C2 0.078(8) 0.050(6) 0.111(9) 0.006(6) 0.014(7) 0.025(6)
C3 0.089(8) 0.037(5) 0.142(11) -0.007(6) 0.019(7) 0.021(5)
C4 0.105(9) 0.081(8) 0.094(8) -0.038(7) -0.015(7) 0.042(7)
C5 0.074(7) 0.049(6) 0.056(6) 0.000(5) -0.005(5) 0.016(5)
C6 0.047(5) 0.049(5) 0.079(7) -0.007(5) 0.004(5) 0.006(4)
C7 0.040(4) 0.050(7) 0.070(5) -0.005(4) 0.005(4) 0.005(4)
C8 0.040(5) 0.055(5) 0.043(5) -0.004(4) 0.007(4) -0.002(4)
C9 0.047(5) 0.070(6) 0.071(6) -0.002(5) 0.023(5) -0.005(4)
C10 0.078(7) 0.082(7) 0.058(6) -0.002(5) 0.024(5) -0.015(6)
C11 0.082(7) 0.074(7) 0.061(6) 0.016(5) 0.015(5) -0.008(6)
C12 0.073(6) 0.058(5) 0.049(5) 0.009(4) 0.011(4) 0.003(5)
C13 0.055(5) 0.041(5) 0.053(5) 0.004(4) 0.007(4) -0.002(4)
C14 0.027(4) 0.042(4) 0.050(4) 0.002(4) 0.000(3) -0.003(3)
C15 0.057(5) 0.039(4) 0.055(5) 0.006(4) 0.003(4) 0.009(4)
C16 0.056(5) 0.045(5) 0.073(6) -0.001(4) 0.006(4) 0.003(4)
C17 0.081(7) 0.044(4) 0.100(7) -0.009(7) 0.016(5) 0.009(7)
C18 0.064(6) 0.062(6) 0.122(8) 0.008(9) 0.036(6) 0.025(7)
C19 0.050(5) 0.068(6) 0.096(8) 0.013(6) 0.003(5) 0.015(5)
C20 0.051(5) 0.055(5) 0.067(6) 0.001(4) -0.002(4) 0.005(4)
C21 0.027(4) 0.040(4) 0.053(5) 0.002(3) 0.009(3) 0.005(3)
C22 0.039(4) 0.047(4) 0.062(4) 0.010(6) 0.002(3) -0.006(5)
C23 0.036(4) 0.033(4) 0.052(4) 0.001(3) 0.011(3) 0.004(3)
C24 0.053(5) 0.055(5) 0.061(5) -0.005(4) 0.022(4) 0.004(4)
C25 0.091(9) 0.125(11) 0.092(9) -0.034(8) 0.041(7) -0.006(8)
C26 0.043(4) 0.050(5) 0.046(4) -0.007(4) 0.001(3) 0.006(4)
C27 0.070(5) 0.052(5) 0.061(5) 0.001(5) 0.008(4) 0.018(6)
C28 0.078(7) 0.058(6) 0.065(6) 0.006(4) 0.000(5) 0.022(5)
C29 0.065(6) 0.086(8) 0.070(6) -0.005(7) -0.012(5) 0.025(7)
C30 0.042(5) 0.080(7) 0.085(7) -0.015(6) -0.003(5) 0.008(5)
C31 0.038(4) 0.051(5) 0.061(5) -0.011(4) 0.001(4) -0.002(4)
C32 0.056(6) 0.077(7) 0.116(9) -0.008(7) 0.034(6) -0.017(5)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni N3 1.848(6) . ?
Ni N2 1.855(7) . ?
Ni O2 1.866(6) . ?
Ni N1 1.967(7) . ?
N1 C6 1.482(11) . ?
N1 C1 1.503(12) . ?
N1 C5 1.499(12) . ?
N2 C7 1.360(10) . ?
N2 C8 1.393(12) . ?
N3 C14 1.301(10) . ?
N3 C21 1.499(10) . ?
O1 C7 1.239(10) . ?
O2 C22 1.313(11) . ?
O3 C22 1.236(9) . ?
O4 C25 1.459(12) . ?
O4 H4 0.8396 . ?
O5 C31 1.379(11) . ?
O5 C32 1.472(11) . ?
C1 C2 1.551(13) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.532(17) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.537(17) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.541(14) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.514(13) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C8 C9 1.418(12) . ?
C8 C13 1.430(12) . ?
C9 C10 1.374(15) . ?
C9 H9 0.9300 . ?
C10 C11 1.362(14) . ?
C10 H10 0.9300 . ?
C11 C12 1.401(13) . ?
C11 H11 0.9300 . ?
C12 C13 1.432(12) . ?
C12 H12 0.9300 . ?
C13 C14 1.450(11) . ?
C14 C15 1.510(11) . ?
C15 C20 1.400(12) . ?
C15 C16 1.412(12) . ?
C16 C17 1.379(13) . ?
C16 H16 0.9300 . ?
C17 C18 1.417(14) . ?
C17 H17 0.9300 . ?
C18 C19 1.352(17) . ?
C18 H18 0.9300 . ?
C19 C20 1.400(13) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.518(13) . ?
C21 C23 1.560(11) . ?
C21 H21 0.9800 . ?
C23 C26 1.515(10) . ?
C23 C24 1.536(10) . ?
C23 H23 0.9800 . ?
C24 C25 1.452(15) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C27 1.371(13) . ?
C26 C31 1.406(11) . ?
C27 C28 1.436(13) . ?
C27 H27 0.9300 . ?
C28 C29 1.347(15) . ?
C28 H28 0.9300 . ?
C29 C30 1.374(17) . ?
C29 H29 0.9300 . ?
C30 C31 1.380(12) . ?
C30 H30 0.9300 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
Cl1 C33 1.78(2) . ?
Cl2 C33 1.96(3) . ?
Cl3 C33 1.82(2) . ?
C33 H33 1.0(5) . ?

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
N3 Ni N2 94.2(3) . . ?
N3 Ni O2 86.3(3) . . ?
N2 Ni O2 178.1(3) . . ?
N3 Ni N1 176.6(3) . . ?
N2 Ni N1 85.7(3) . . ?
O2 Ni N1 93.8(3) . . ?
C6 N1 C1 112.6(8) . . ?
C6 N1 C5 111.7(7) . . ?
C1 N1 C5 109.7(7) . . ?
C6 N1 Ni 102.6(5) . . ?
C1 N1 Ni 113.0(5) . . ?
C5 N1 Ni 107.0(5) . . ?
C7 N2 C8 122.0(7) . . ?
C7 N2 Ni 113.7(6) . . ?
C8 N2 Ni 124.2(6) . . ?
C14 N3 C21 120.1(6) . . ?
C14 N3 Ni 128.9(5) . . ?
C21 N3 Ni 110.9(5) . . ?
C22 O2 Ni 113.4(5) . . ?
C25 O4 H4 110.5 . . ?
C31 O5 C32 117.7(7) . . ?
N1 C1 C2 112.4(8) . . ?
N1 C1 H1A 109.2 . . ?
C2 C1 H1A 109.1 . . ?
N1 C1 H1B 109.0 . . ?
C2 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
C3 C2 C1 110.2(9) . . ?
C3 C2 H2A 109.7 . . ?
C1 C2 H2A 109.6 . . ?
C3 C2 H2B 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C4 C3 C2 109.2(9) . . ?
C4 C3 H3A 109.8 . . ?
C2 C3 H3A 109.8 . . ?
C4 C3 H3B 109.8 . . ?
C2 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
C3 C4 C5 110.3(10) . . ?
C3 C4 H4A 109.7 . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C5 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
N1 C5 C4 113.8(8) . . ?
N1 C5 H5A 108.8 . . ?
C4 C5 H5A 108.8 . . ?
N1 C5 H5B 108.8 . . ?
C4 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
N1 C6 C7 111.8(7) . . ?
N1 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
N1 C6 H6B 109.2 . . ?
C7 C6 H6B 109.0 . . ?
H6A C6 H6B 107.9 . . ?
O1 C7 N2 127.9(8) . . ?
O1 C7 C6 120.2(8) . . ?
N2 C7 C6 111.9(7) . . ?
N2 C8 C9 121.4(8) . . ?
N2 C8 C13 121.0(7) . . ?
C9 C8 C13 117.5(8) . . ?
C10 C9 C8 121.6(9) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.1 . . ?
C11 C10 C9 121.9(9) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.0 . . ?
C10 C11 C12 119.3(10) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.5 . . ?
C11 C12 C13 120.8(9) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C8 C13 C12 118.8(8) . . ?
C8 C13 C14 123.9(7) . . ?
C12 C13 C14 117.4(8) . . ?
N3 C14 C13 121.7(7) . . ?
N3 C14 C15 120.9(7) . . ?
C13 C14 C15 117.4(7) . . ?
C20 C15 C16 119.7(8) . . ?
C20 C15 C14 119.0(8) . . ?
C16 C15 C14 121.2(8) . . ?
C17 C16 C15 121.0(9) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C18 118.3(11) . . ?
C16 C17 H17 120.8 . . ?
C18 C17 H17 120.9 . . ?
C19 C18 C17 120.7(11) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 121.9(10) . . ?
C18 C19 H19 119.1 . . ?
C20 C19 H19 119.0 . . ?
C19 C20 C15 118.3(9) . . ?
C19 C20 H20 120.8 . . ?
C15 C20 H20 120.9 . . ?
N3 C21 C22 105.2(6) . . ?
N3 C21 C23 109.8(6) . . ?
C22 C21 C23 111.4(6) . . ?
N3 C21 H21 110.1 . . ?
C22 C21 H21 110.1 . . ?
C23 C21 H21 110.2 . . ?
O3 C22 O2 121.5(9) . . ?
O3 C22 C21 121.6(8) . . ?
O2 C22 C21 116.8(7) . . ?
C26 C23 C24 114.5(7) . . ?
C26 C23 C21 113.4(6) . . ?
C24 C23 C21 111.8(6) . . ?
C26 C23 H23 105.3 . . ?
C24 C23 H23 105.4 . . ?
C21 C23 H23 105.4 . . ?
C25 C24 C23 112.3(8) . . ?
C25 C24 H24A 109.0 . . ?
C23 C24 H24A 109.1 . . ?
C25 C24 H24B 109.2 . . ?
C23 C24 H24B 109.2 . . ?
H24A C24 H24B 107.9 . . ?
C24 C25 O4 112.2(10) . . ?
C24 C25 H25A 109.2 . . ?
O4 C25 H25A 109.5 . . ?
C24 C25 H25B 109.0 . . ?
O4 C25 H25B 109.1 . . ?
H25A C25 H25B 107.8 . . ?
C27 C26 C31 115.9(8) . . ?
C27 C26 C23 122.2(8) . . ?
C31 C26 C23 121.8(7) . . ?
C26 C27 C28 123.6(9) . . ?
C26 C27 H27 118.3 . . ?
C28 C27 H27 118.0 . . ?
C29 C28 C27 116.9(10) . . ?
C29 C28 H28 121.6 . . ?
C27 C28 H28 121.5 . . ?
C28 C29 C30 121.8(10) . . ?
C28 C29 H29 119.0 . . ?
C30 C29 H29 119.1 . . ?
C29 C30 C31 120.3(10) . . ?
C29 C30 H30 119.9 . . ?
C31 C30 H30 119.8 . . ?
C30 C31 O5 123.0(8) . . ?
C30 C31 C26 121.4(9) . . ?
O5 C31 C26 115.7(7) . . ?
O5 C32 H32A 109.2 . . ?
O5 C32 H32B 109.6 . . ?
H32A C32 H32B 109.5 . . ?
O5 C32 H32C 109.6 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
Cl1 C33 Cl3 114.0(18) . . ?
Cl1 C33 Cl2 84.6(19) . . ?
Cl3 C33 Cl2 143(10) . . ?
Cl1 C33 H33 103(8) . . ?
Cl3 C33 H33 102(7) . . ?
Cl2 C33 H33 104(10) . . ?

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
N3 Ni N1 C6 -56(5) . . . . ?
N2 Ni N1 C6 33.5(6) . . . . ?
O2 Ni N1 C6 -148.3(5) . . . . ?
N3 Ni N1 C1 66(5) . . . . ?
N2 Ni N1 C1 155.0(7) . . . . ?
O2 Ni N1 C1 -26.8(7) . . . . ?
N3 Ni N1 C5 -173(5) . . . . ?
N2 Ni N1 C5 -84.2(6) . . . . ?
O2 Ni N1 C5 94.0(6) . . . . ?
N3 Ni N2 C7 149.1(6) . . . . ?
O2 Ni N2 C7 -104(10) . . . . ?
N1 Ni N2 C7 -27.6(6) . . . . ?
N3 Ni N2 C8 -27.2(7) . . . . ?
O2 Ni N2 C8 80(10) . . . . ?
N1 Ni N2 C8 156.1(7) . . . . ?
N2 Ni N3 C14 18.7(7) . . . . ?
O2 Ni N3 C14 -159.5(7) . . . . ?
N1 Ni N3 C14 108(5) . . . . ?
N2 Ni N3 C21 -156.7(5) . . . . ?
O2 Ni N3 C21 25.1(5) . . . . ?
N1 Ni N3 C21 -68(5) . . . . ?
N3 Ni O2 C22 -16.7(5) . . . . ?
N2 Ni O2 C22 -124(10) . . . . ?
N1 Ni O2 C22 159.9(6) . . . . ?
C6 N1 C1 C2 -69.9(11) . . . . ?
C5 N1 C1 C2 55.1(11) . . . . ?
Ni N1 C1 C2 174.4(7) . . . . ?
N1 C1 C2 C3 -58.2(12) . . . . ?
C1 C2 C3 C4 57.4(12) . . . . ?
C2 C3 C4 C5 -56.1(13) . . . . ?
C6 N1 C5 C4 71.1(12) . . . . ?
C1 N1 C5 C4 -54.5(12) . . . . ?
Ni N1 C5 C4 -177.4(9) . . . . ?
C3 C4 C5 N1 56.0(14) . . . . ?
C1 N1 C6 C7 -156.2(7) . . . . ?
C5 N1 C6 C7 79.9(9) . . . . ?
Ni N1 C6 C7 -34.4(8) . . . . ?
C8 N2 C7 O1 10.0(15) . . . . ?
Ni N2 C7 O1 -166.4(8) . . . . ?
C8 N2 C7 C6 -170.9(8) . . . . ?
Ni N2 C7 C6 12.7(9) . . . . ?
N1 C6 C7 O1 -164.4(8) . . . . ?
N1 C6 C7 N2 16.4(11) . . . . ?
C7 N2 C8 C9 27.3(13) . . . . ?
Ni N2 C8 C9 -156.7(7) . . . . ?
C7 N2 C8 C13 -154.2(8) . . . . ?
Ni N2 C8 C13 21.8(12) . . . . ?
N2 C8 C9 C10 177.6(9) . . . . ?
C13 C8 C9 C10 -0.9(14) . . . . ?
C8 C9 C10 C11 3.3(16) . . . . ?
C9 C10 C11 C12 -3.7(16) . . . . ?
C10 C11 C12 C13 1.8(15) . . . . ?
N2 C8 C13 C12 -179.4(8) . . . . ?
C9 C8 C13 C12 -1.0(13) . . . . ?
N2 C8 C13 C14 0.9(14) . . . . ?
C9 C8 C13 C14 179.3(8) . . . . ?
C11 C12 C13 C8 0.5(14) . . . . ?
C11 C12 C13 C14 -179.8(9) . . . . ?
C21 N3 C14 C13 171.6(7) . . . . ?
Ni N3 C14 C13 -3.4(11) . . . . ?
C21 N3 C14 C15 -6.3(11) . . . . ?
Ni N3 C14 C15 178.6(6) . . . . ?
C8 C13 C14 N3 -10.7(13) . . . . ?
C12 C13 C14 N3 169.6(8) . . . . ?
C8 C13 C14 C15 167.4(8) . . . . ?
C12 C13 C14 C15 -12.3(11) . . . . ?
N3 C14 C15 C20 -81.4(10) . . . . ?
C13 C14 C15 C20 100.6(9) . . . . ?
N3 C14 C15 C16 102.3(10) . . . . ?
C13 C14 C15 C16 -75.7(11) . . . . ?
C20 C15 C16 C17 2.0(14) . . . . ?
C14 C15 C16 C17 178.3(8) . . . . ?
C15 C16 C17 C18 -3.6(15) . . . . ?
C16 C17 C18 C19 2.3(16) . . . . ?
C17 C18 C19 C20 0.6(17) . . . . ?
C18 C19 C20 C15 -2.2(15) . . . . ?
C16 C15 C20 C19 0.9(13) . . . . ?
C14 C15 C20 C19 -175.4(8) . . . . ?
C14 N3 C21 C22 157.1(6) . . . . ?
Ni N3 C21 C22 -27.0(7) . . . . ?
C14 N3 C21 C23 -83.0(8) . . . . ?
Ni N3 C21 C23 92.9(6) . . . . ?
Ni O2 C22 O3 -173.6(6) . . . . ?
Ni O2 C22 C21 3.8(8) . . . . ?
N3 C21 C22 O3 -167.6(7) . . . . ?
C23 C21 C22 O3 73.6(9) . . . . ?
N3 C21 C22 O2 15.0(9) . . . . ?
C23 C21 C22 O2 -103.8(8) . . . . ?
N3 C21 C23 C26 -55.1(8) . . . . ?
C22 C21 C23 C26 60.9(8) . . . . ?
N3 C21 C23 C24 173.5(7) . . . . ?
C22 C21 C23 C24 -70.4(8) . . . . ?
C26 C23 C24 C25 62.4(11) . . . . ?
C21 C23 C24 C25 -166.8(9) . . . . ?
C23 C24 C25 O4 -179.0(10) . . . . ?
C24 C23 C26 C27 42.2(11) . . . . ?
C21 C23 C26 C27 -87.7(9) . . . . ?
C24 C23 C26 C31 -135.7(8) . . . . ?
C21 C23 C26 C31 94.4(9) . . . . ?
C31 C26 C27 C28 0.7(13) . . . . ?
C23 C26 C27 C28 -177.3(8) . . . . ?
C26 C27 C28 C29 0.2(15) . . . . ?
C27 C28 C29 C30 -0.8(15) . . . . ?
C28 C29 C30 C31 0.4(16) . . . . ?
C29 C30 C31 O5 -179.6(8) . . . . ?
C29 C30 C31 C26 0.6(14) . . . . ?
C32 O5 C31 C30 5.4(12) . . . . ?
C32 O5 C31 C26 -174.8(8) . . . . ?
C27 C26 C31 C30 -1.1(12) . . . . ?
C23 C26 C31 C30 177.0(8) . . . . ?
C27 C26 C31 O5 179.1(7) . . . . ?
C23 C26 C31 O5 -2.9(11) . . . . ?

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
O4 H4 O3 0.84 2.49 2.781(11) 101.2 2_557

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.823
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.105