# Supplementary Material (ESI) for Dalton Transactions
# This journal is (c) The Royal Society of Chemistry 2011


data_global
_journal_name_full               'Dalton Trans.'

_journal_coden_Cambridge         0222
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Sun, Wen Hua'
_publ_contact_author_email       whsun@iccas.ac.cn

_publ_section_title              
;
Synthesis, characterization and ethylene
oligomerization behavior of 2-benzoimidazol-8-ethoxyquinolylnickel
dihalides
;
loop_
_publ_author_name
H.Liu
L.Zhang
L.Chen
C.Redshaw
Y.Li
W.H.Sun

# Attachment '- CIF.CIF'

data_C1
_database_code_depnum_ccdc_archive 'CCDC 795581'
#TrackingRef '- CIF.CIF'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 Cl2 N3 Ni O2'
_chemical_formula_weight         464.00

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6203(19)
_cell_length_b                   10.122(2)
_cell_length_c                   11.824(2)
_cell_angle_alpha                79.28(3)
_cell_angle_beta                 73.28(3)
_cell_angle_gamma                64.71(3)
_cell_volume                     994.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2957
_cell_measurement_theta_min      1.8031
_cell_measurement_theta_max      27.4779

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             478
_exptl_absorpt_coefficient_mu    1.266
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_min  0.7595
_exptl_absorpt_correction_T_max  0.8946
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            12256
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0402
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         27.46
_reflns_number_total             4530
_reflns_number_gt                4075
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Siemens SMART'
_computing_cell_refinement       'Siemens SMART & SAINT'
_computing_data_reduction        'Siemens XPREP'
_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^)+(0.0648P)^2^+1.0181P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4530
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1483
_refine_ls_wR_factor_gt          0.1383
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_restrained_S_all      1.183
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.43499(5) 0.75743(4) 0.31534(3) 0.02494(15) Uani 1 1 d . . .
Cl2 Cl 0.26286(10) 1.00901(9) 0.32447(7) 0.0315(2) Uani 1 1 d . . .
Cl1 Cl 0.61404(11) 0.50570(9) 0.33121(7) 0.0355(2) Uani 1 1 d . . .
N3 N 0.5945(3) 0.8092(3) 0.1830(2) 0.0251(5) Uani 1 1 d . . .
O1 O 0.5885(3) 0.8118(3) 0.40523(19) 0.0315(5) Uani 1 1 d . . .
N2 N 0.3800(3) 0.7262(3) 0.1704(2) 0.0258(6) Uani 1 1 d . . .
N1 N 0.4484(4) 0.7099(3) -0.0253(2) 0.0304(6) Uani 1 1 d . . .
C8 C 0.7627(4) 0.9432(4) 0.3517(3) 0.0331(7) Uani 1 1 d . . .
H8A H 0.7622 0.9463 0.4317 0.040 Uiso 1 1 calc R . .
C17 C 0.6110(5) 0.7726(4) 0.5250(3) 0.0354(8) Uani 1 1 d . . .
H17A H 0.5259 0.7428 0.5752 0.043 Uiso 1 1 calc R . .
H17B H 0.6032 0.8595 0.5576 0.043 Uiso 1 1 calc R . .
C1 C 0.5925(4) 0.8019(3) 0.0721(3) 0.0251(6) Uani 1 1 d . . .
C16 C 0.4768(4) 0.7446(3) 0.0695(3) 0.0271(7) Uani 1 1 d . . .
C5 C 0.6823(4) 0.8714(3) 0.2054(3) 0.0258(6) Uani 1 1 d . . .
C2 C 0.6812(4) 0.8586(4) -0.0253(3) 0.0302(7) Uani 1 1 d . . .
H2A H 0.6812 0.8503 -0.1040 0.036 Uiso 1 1 calc R . .
C10 C 0.2792(4) 0.6791(4) 0.1423(3) 0.0299(7) Uani 1 1 d . . .
C4 C 0.7700(4) 0.9358(4) 0.1124(3) 0.0283(7) Uani 1 1 d . . .
C15 C 0.3224(4) 0.6679(4) 0.0190(3) 0.0332(7) Uani 1 1 d . . .
C6 C 0.8528(4) 1.0056(4) 0.1428(3) 0.0341(8) Uani 1 1 d . . .
H6A H 0.9114 1.0508 0.0826 0.041 Uiso 1 1 calc R . .
C9 C 0.6798(4) 0.8755(4) 0.3255(3) 0.0286(7) Uani 1 1 d . . .
C3 C 0.7670(4) 0.9254(4) -0.0043(3) 0.0312(7) Uani 1 1 d . . .
H3A H 0.8257 0.9655 -0.0691 0.037 Uiso 1 1 calc R . .
C19 C 0.5331(5) 0.7087(4) -0.1499(3) 0.0375(8) Uani 1 1 d . . .
H19A H 0.6172 0.7431 -0.1598 0.056 Uiso 1 1 calc R . .
H19B H 0.4592 0.7734 -0.1984 0.056 Uiso 1 1 calc R . .
H19C H 0.5796 0.6087 -0.1750 0.056 Uiso 1 1 calc R . .
C14 C 0.2426(5) 0.6234(4) -0.0370(4) 0.0461(10) Uani 1 1 d . . .
H14A H 0.2723 0.6150 -0.1200 0.055 Uiso 1 1 calc R . .
C11 C 0.1539(4) 0.6468(4) 0.2132(4) 0.0372(8) Uani 1 1 d . . .
H11A H 0.1245 0.6543 0.2963 0.045 Uiso 1 1 calc R . .
C18 C 0.7690(5) 0.6496(5) 0.5296(4) 0.0484(10) Uani 1 1 d . . .
H18A H 0.7797 0.6267 0.6118 0.073 Uiso 1 1 calc R . .
H18B H 0.8537 0.6793 0.4811 0.073 Uiso 1 1 calc R . .
H18C H 0.7764 0.5626 0.4991 0.073 Uiso 1 1 calc R . .
C12 C 0.0734(5) 0.6034(4) 0.1583(4) 0.0486(10) Uani 1 1 d . . .
H12A H -0.0134 0.5806 0.2042 0.058 Uiso 1 1 calc R . .
C7 C 0.8483(4) 1.0078(4) 0.2592(3) 0.0374(8) Uani 1 1 d . . .
H7A H 0.9050 1.0546 0.2782 0.045 Uiso 1 1 calc R . .
C13 C 0.1185(6) 0.5923(5) 0.0347(4) 0.0521(11) Uani 1 1 d . . .
H13A H 0.0605 0.5622 -0.0004 0.063 Uiso 1 1 calc R . .
O2 O 0.2873(3) 0.6977(3) 0.4554(2) 0.0382(6) Uiso 1 1 d . . .
C20 C 0.1277(4) 0.7794(4) 0.5144(3) 0.0394(8) Uiso 1 1 d . . .
H20A H 0.0910 0.7168 0.5786 0.059 Uiso 1 1 calc R . .
H20B H 0.0602 0.8135 0.4578 0.059 Uiso 1 1 calc R . .
H20C H 0.1224 0.8639 0.5473 0.059 Uiso 1 1 calc R . .

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
Ni1 0.0303(2) 0.0267(2) 0.0195(2) -0.00066(16) -0.00546(17) -0.01352(18)
Cl2 0.0381(4) 0.0278(4) 0.0258(4) -0.0022(3) -0.0046(3) -0.0122(3)
Cl1 0.0448(5) 0.0292(4) 0.0270(4) -0.0014(3) -0.0097(4) -0.0089(4)
N3 0.0299(13) 0.0250(13) 0.0210(12) -0.0017(10) -0.0074(10) -0.0104(11)
O1 0.0399(13) 0.0408(14) 0.0215(11) 0.0013(10) -0.0079(10) -0.0242(11)
N2 0.0314(14) 0.0242(13) 0.0250(13) -0.0017(10) -0.0099(11) -0.0120(11)
N1 0.0414(16) 0.0268(14) 0.0243(14) -0.0045(11) -0.0105(12) -0.0121(12)
C8 0.0414(19) 0.0366(19) 0.0280(17) -0.0017(14) -0.0113(15) -0.0199(15)
C17 0.049(2) 0.047(2) 0.0192(15) 0.0013(14) -0.0097(14) -0.0274(18)
C1 0.0290(15) 0.0226(15) 0.0201(14) -0.0012(11) -0.0085(12) -0.0053(12)
C16 0.0322(16) 0.0258(16) 0.0225(15) -0.0010(12) -0.0089(13) -0.0094(13)
C5 0.0270(15) 0.0260(15) 0.0244(15) -0.0035(12) -0.0062(12) -0.0098(12)
C2 0.0325(17) 0.0321(17) 0.0203(15) -0.0007(13) -0.0044(13) -0.0091(14)
C10 0.0355(17) 0.0244(16) 0.0343(18) -0.0008(13) -0.0161(14) -0.0113(13)
C4 0.0263(15) 0.0286(16) 0.0271(16) 0.0008(13) -0.0051(13) -0.0102(13)
C15 0.0426(19) 0.0260(16) 0.0344(18) -0.0029(13) -0.0171(15) -0.0112(14)
C6 0.0343(18) 0.0375(19) 0.0338(18) 0.0025(14) -0.0050(14) -0.0212(15)
C9 0.0294(16) 0.0321(17) 0.0250(16) -0.0008(13) -0.0058(13) -0.0137(13)
C3 0.0275(16) 0.0354(18) 0.0253(16) 0.0044(13) -0.0042(13) -0.0114(14)
C19 0.050(2) 0.0349(19) 0.0237(17) -0.0059(14) -0.0114(15) -0.0103(16)
C14 0.064(3) 0.040(2) 0.047(2) -0.0014(18) -0.030(2) -0.024(2)
C11 0.0392(19) 0.0279(18) 0.045(2) -0.0016(15) -0.0128(16) -0.0122(15)
C18 0.065(3) 0.043(2) 0.047(2) 0.0087(18) -0.029(2) -0.027(2)
C12 0.044(2) 0.038(2) 0.074(3) 0.002(2) -0.024(2) -0.0216(18)
C7 0.0399(19) 0.043(2) 0.040(2) -0.0033(16) -0.0110(16) -0.0252(17)
C13 0.066(3) 0.049(2) 0.064(3) -0.002(2) -0.035(2) -0.032(2)

_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 N3 2.020(3) . ?
Ni1 O2 2.034(3) . ?
Ni1 N2 2.045(3) . ?
Ni1 O1 2.329(2) . ?
Ni1 Cl2 2.3738(13) . ?
Ni1 Cl1 2.3984(13) . ?
N3 C1 1.333(4) . ?
N3 C5 1.351(4) . ?
O1 C9 1.364(4) . ?
O1 C17 1.451(4) . ?
N2 C16 1.324(4) . ?
N2 C10 1.385(4) . ?
N1 C16 1.363(4) . ?
N1 C15 1.385(5) . ?
N1 C19 1.463(4) . ?
C8 C9 1.375(5) . ?
C8 C7 1.406(5) . ?
C17 C18 1.506(6) . ?
C1 C2 1.411(5) . ?
C1 C16 1.467(5) . ?
C5 C4 1.420(4) . ?
C5 C9 1.421(4) . ?
C2 C3 1.363(5) . ?
C10 C11 1.383(5) . ?
C10 C15 1.409(5) . ?
C4 C3 1.412(5) . ?
C4 C6 1.415(5) . ?
C15 C14 1.388(5) . ?
C6 C7 1.368(5) . ?
C14 C13 1.372(6) . ?
C11 C12 1.379(5) . ?
C12 C13 1.411(6) . ?
O2 C20 1.428(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Ni1 O2 175.74(10) . . ?
N3 Ni1 N2 79.03(11) . . ?
O2 Ni1 N2 104.24(11) . . ?
N3 Ni1 O1 73.60(9) . . ?
O2 Ni1 O1 103.01(9) . . ?
N2 Ni1 O1 152.55(10) . . ?
N3 Ni1 Cl2 90.17(9) . . ?
O2 Ni1 Cl2 92.21(9) . . ?
N2 Ni1 Cl2 95.73(8) . . ?
O1 Ni1 Cl2 86.45(7) . . ?
N3 Ni1 Cl1 92.41(9) . . ?
O2 Ni1 Cl1 84.79(9) . . ?
N2 Ni1 Cl1 91.87(8) . . ?
O1 Ni1 Cl1 87.33(7) . . ?
Cl2 Ni1 Cl1 172.31(3) . . ?
C1 N3 C5 120.7(3) . . ?
C1 N3 Ni1 117.8(2) . . ?
C5 N3 Ni1 120.6(2) . . ?
C9 O1 C17 118.7(3) . . ?
C9 O1 Ni1 111.50(19) . . ?
C17 O1 Ni1 129.4(2) . . ?
C16 N2 C10 106.6(3) . . ?
C16 N2 Ni1 113.0(2) . . ?
C10 N2 Ni1 140.1(2) . . ?
C16 N1 C15 106.3(3) . . ?
C16 N1 C19 129.3(3) . . ?
C15 N1 C19 124.4(3) . . ?
C9 C8 C7 119.4(3) . . ?
O1 C17 C18 112.0(3) . . ?
N3 C1 C2 121.4(3) . . ?
N3 C1 C16 111.2(3) . . ?
C2 C1 C16 127.1(3) . . ?
N2 C16 N1 112.4(3) . . ?
N2 C16 C1 118.5(3) . . ?
N1 C16 C1 129.1(3) . . ?
N3 C5 C4 121.2(3) . . ?
N3 C5 C9 118.1(3) . . ?
C4 C5 C9 120.7(3) . . ?
C3 C2 C1 118.8(3) . . ?
C11 C10 N2 130.9(3) . . ?
C11 C10 C15 121.2(3) . . ?
N2 C10 C15 107.9(3) . . ?
C3 C4 C6 125.0(3) . . ?
C3 C4 C5 116.9(3) . . ?
C6 C4 C5 118.1(3) . . ?
N1 C15 C14 131.4(4) . . ?
N1 C15 C10 106.7(3) . . ?
C14 C15 C10 121.9(4) . . ?
C7 C6 C4 119.9(3) . . ?
O1 C9 C8 126.2(3) . . ?
O1 C9 C5 114.2(3) . . ?
C8 C9 C5 119.6(3) . . ?
C2 C3 C4 121.0(3) . . ?
C13 C14 C15 116.1(4) . . ?
C12 C11 C10 117.4(4) . . ?
C11 C12 C13 120.8(4) . . ?
C6 C7 C8 122.3(3) . . ?
C14 C13 C12 122.7(4) . . ?
C20 O2 Ni1 130.6(2) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.931
_refine_diff_density_min         -0.719
_refine_diff_density_rms         0.175
#==End

data_C6
_database_code_depnum_ccdc_archive 'CCDC 795582'
#TrackingRef '- CIF.CIF'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H20 Cl3 N3 Ni O'
_chemical_formula_weight         495.46

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   10.661(2)
_cell_length_b                   14.747(3)
_cell_length_c                   12.948(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.21(3)
_cell_angle_gamma                90.00
_cell_volume                     2027.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6381
_cell_measurement_theta_min      2.10
_cell_measurement_theta_max      27.44

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016
_exptl_absorpt_coefficient_mu    1.371
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.6169
_exptl_absorpt_correction_T_max  0.8865

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            16263
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_sigmaI/netI    0.0540
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         27.44
_reflns_number_total             4623
_reflns_number_gt                4204
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Siemens SMART'
_computing_cell_refinement       'Siemens SMART & SAINT'
_computing_data_reduction        'Siemens XPREP'
_computing_structure_solution    'Siemens SHELXTL'
_computing_structure_refinement  'Siemens SHELXTL'
_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^)+(0.0581P)^2^+2.5357P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4623
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_ref          0.0746
_refine_ls_R_factor_gt           0.0667
_refine_ls_wR_factor_ref         0.1625
_refine_ls_wR_factor_gt          0.1583
_refine_ls_goodness_of_fit_ref   1.293
_refine_ls_restrained_S_all      1.293
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.61244(5) 0.04541(4) 0.10110(4) 0.02044(17) Uani 1 1 d . . .
Cl1 Cl 0.39182(9) 0.02051(7) 0.07447(8) 0.0242(2) Uani 1 1 d . . .
Cl2 Cl 0.61964(11) 0.08933(9) 0.27319(8) 0.0331(3) Uani 1 1 d . . .
Cl3 Cl 0.19809(11) 0.34712(8) 0.03463(10) 0.0371(3) Uani 1 1 d . . .
N3 N 0.8016(3) 0.0612(2) 0.0935(3) 0.0192(7) Uani 1 1 d . . .
O1 O 0.7140(3) -0.0929(2) 0.1680(2) 0.0267(7) Uani 1 1 d . . .
C4 C 1.0188(4) 0.0163(3) 0.1371(3) 0.0229(9) Uani 1 1 d . . .
C6 C 1.1036(4) -0.0490(3) 0.1835(4) 0.0284(10) Uani 1 1 d . . .
H6A H 1.1919 -0.0391 0.1868 0.034 Uiso 1 1 calc R . .
C11 C 0.4119(4) 0.2512(3) 0.0388(3) 0.0251(9) Uani 1 1 d . . .
H11A H 0.3693 0.2053 0.0735 0.030 Uiso 1 1 calc R . .
N1 N 0.7261(3) 0.2800(2) -0.0314(3) 0.0224(7) Uani 1 1 d . . .
C5 C 0.8867(4) 0.0003(3) 0.1342(3) 0.0205(8) Uani 1 1 d . . .
C12 C 0.3531(4) 0.3298(3) 0.0045(4) 0.0260(9) Uani 1 1 d . . .
C9 C 0.8419(4) -0.0827(3) 0.1758(3) 0.0260(9) Uani 1 1 d . . .
C16 C 0.7316(4) 0.1977(3) 0.0192(3) 0.0203(8) Uani 1 1 d . . .
C1 C 0.8396(4) 0.1388(3) 0.0525(3) 0.0207(8) Uani 1 1 d . . .
N2 N 0.6199(3) 0.1732(2) 0.0474(3) 0.0213(7) Uani 1 1 d . . .
C10 C 0.5382(4) 0.2428(3) 0.0196(3) 0.0237(9) Uani 1 1 d . . .
C2 C 0.9691(4) 0.1597(3) 0.0533(3) 0.0244(9) Uani 1 1 d . . .
H2A H 0.9956 0.2156 0.0259 0.029 Uiso 1 1 calc R . .
C3 C 1.0556(4) 0.0981(3) 0.0942(3) 0.0250(9) Uani 1 1 d . . .
H3A H 1.1428 0.1112 0.0935 0.030 Uiso 1 1 calc R . .
C21 C 0.7803(5) 0.3451(4) -0.1984(4) 0.0341(11) Uani 1 1 d . . .
H21A H 0.7485 0.2895 -0.2330 0.051 Uiso 1 1 calc R . .
H21B H 0.8501 0.3692 -0.2344 0.051 Uiso 1 1 calc R . .
H21C H 0.7126 0.3901 -0.2000 0.051 Uiso 1 1 calc R . .
C13 C 0.4128(4) 0.3971(3) -0.0487(4) 0.0303(10) Uani 1 1 d . . .
H13A H 0.3667 0.4493 -0.0727 0.036 Uiso 1 1 calc R . .
C20 C 0.8772(5) 0.4071(3) -0.0283(4) 0.0354(11) Uani 1 1 d . . .
H20A H 0.9057 0.3902 0.0432 0.053 Uiso 1 1 calc R . .
H20B H 0.8106 0.4529 -0.0279 0.053 Uiso 1 1 calc R . .
H20C H 0.9481 0.4320 -0.0622 0.053 Uiso 1 1 calc R . .
C7 C 1.0573(4) -0.1264(3) 0.2236(4) 0.0305(10) Uani 1 1 d . . .
H7A H 1.1146 -0.1693 0.2559 0.037 Uiso 1 1 calc R . .
C14 C 0.5384(4) 0.3891(3) -0.0673(4) 0.0302(10) Uani 1 1 d . . .
H14A H 0.5796 0.4348 -0.1033 0.036 Uiso 1 1 calc R . .
C8 C 0.9266(4) -0.1448(3) 0.2186(4) 0.0292(10) Uani 1 1 d . . .
H8A H 0.8977 -0.2003 0.2450 0.035 Uiso 1 1 calc R . .
C15 C 0.6020(4) 0.3104(3) -0.0306(3) 0.0233(9) Uani 1 1 d . . .
C19 C 0.8264(4) 0.3241(3) -0.0869(3) 0.0255(9) Uani 1 1 d . . .
H19A H 0.8973 0.2798 -0.0881 0.031 Uiso 1 1 calc R . .
C18 C 0.5273(5) -0.1544(4) 0.2329(4) 0.0363(11) Uani 1 1 d . . .
H18A H 0.4946 -0.2029 0.2747 0.054 Uiso 1 1 calc R . .
H18D H 0.4864 -0.1575 0.1621 0.054 Uiso 1 1 calc R . .
H18B H 0.5096 -0.0955 0.2634 0.054 Uiso 1 1 calc R . .
C17 C 0.6667(5) -0.1656(3) 0.2306(4) 0.0328(11) Uani 1 1 d . . .
H17C H 0.7086 -0.1630 0.3020 0.039 Uiso 1 1 calc R . .
H17A H 0.6853 -0.2252 0.2003 0.039 Uiso 1 1 calc R . .

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
Ni1 0.0170(3) 0.0219(3) 0.0224(3) 0.0009(2) 0.0022(2) -0.0021(2)
Cl1 0.0180(5) 0.0286(5) 0.0264(5) -0.0036(4) 0.0038(4) -0.0027(4)
Cl2 0.0303(6) 0.0457(7) 0.0236(5) -0.0054(5) 0.0036(5) -0.0027(5)
Cl3 0.0226(5) 0.0375(6) 0.0518(8) 0.0068(6) 0.0076(5) 0.0074(5)
N3 0.0179(16) 0.0208(17) 0.0187(17) -0.0004(14) 0.0008(13) 0.0024(13)
O1 0.0248(15) 0.0255(15) 0.0296(16) 0.0081(13) 0.0021(13) -0.0024(12)
C4 0.019(2) 0.027(2) 0.022(2) -0.0029(17) -0.0014(16) -0.0005(16)
C6 0.021(2) 0.034(2) 0.029(2) -0.0029(19) -0.0022(18) 0.0043(18)
C11 0.019(2) 0.026(2) 0.031(2) -0.0011(18) 0.0056(17) 0.0015(17)
N1 0.0166(16) 0.0234(17) 0.0269(18) 0.0034(15) 0.0008(14) -0.0011(13)
C5 0.019(2) 0.023(2) 0.019(2) -0.0011(16) -0.0006(16) -0.0001(16)
C12 0.019(2) 0.027(2) 0.031(2) 0.0007(19) 0.0019(18) 0.0031(17)
C9 0.023(2) 0.029(2) 0.026(2) 0.0002(18) 0.0025(18) -0.0005(18)
C16 0.0207(19) 0.0194(19) 0.021(2) -0.0021(16) 0.0022(16) -0.0033(15)
C1 0.0179(19) 0.024(2) 0.021(2) -0.0012(16) 0.0020(16) -0.0021(16)
N2 0.0177(17) 0.0196(16) 0.0264(18) 0.0009(14) 0.0014(14) -0.0005(13)
C10 0.022(2) 0.023(2) 0.025(2) 0.0006(17) -0.0011(17) 0.0000(16)
C2 0.0151(19) 0.029(2) 0.029(2) 0.0014(18) -0.0001(17) -0.0037(16)
C3 0.019(2) 0.028(2) 0.027(2) -0.0004(18) 0.0019(17) -0.0013(17)
C21 0.031(2) 0.043(3) 0.029(2) 0.010(2) 0.006(2) 0.009(2)
C13 0.027(2) 0.024(2) 0.040(3) 0.005(2) 0.003(2) 0.0052(18)
C20 0.030(2) 0.034(3) 0.042(3) -0.002(2) 0.007(2) -0.010(2)
C7 0.030(2) 0.032(2) 0.028(2) 0.0070(19) -0.0008(19) 0.0100(19)
C14 0.027(2) 0.021(2) 0.042(3) 0.007(2) 0.004(2) -0.0002(18)
C8 0.033(2) 0.025(2) 0.030(2) 0.0039(19) 0.0020(19) 0.0043(19)
C15 0.019(2) 0.023(2) 0.028(2) -0.0018(18) 0.0032(17) 0.0004(16)
C19 0.021(2) 0.025(2) 0.031(2) 0.0046(18) 0.0072(18) -0.0019(17)
C18 0.034(3) 0.042(3) 0.033(3) 0.011(2) 0.004(2) -0.014(2)
C17 0.040(3) 0.028(2) 0.031(2) 0.008(2) 0.007(2) -0.003(2)

_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 2.012(3) . ?
Ni1 N3 2.041(3) . ?
Ni1 Cl2 2.3151(13) . ?
Ni1 Cl1 2.3746(12) . ?
Ni1 Cl1 2.4690(12) 3_655 ?
Cl1 Ni1 2.4690(12) 3_655 ?
Cl3 C12 1.751(4) . ?
N3 C1 1.340(5) . ?
N3 C5 1.349(5) . ?
O1 C9 1.366(5) . ?
O1 C17 1.461(5) . ?
C4 C3 1.399(6) . ?
C4 C6 1.418(6) . ?
C4 C5 1.425(6) . ?
C6 C7 1.364(6) . ?
C6 H6A 0.9500 . ?
C11 C12 1.373(6) . ?
C11 C10 1.397(6) . ?
C11 H11A 0.9500 . ?
N1 C16 1.378(5) . ?
N1 C15 1.398(5) . ?
N1 C19 1.491(5) . ?
C5 C9 1.437(6) . ?
C12 C13 1.395(6) . ?
C9 C8 1.367(6) . ?
C16 N2 1.327(5) . ?
C16 C1 1.475(6) . ?
C1 C2 1.414(5) . ?
N2 C10 1.373(5) . ?
C10 C15 1.400(6) . ?
C2 C3 1.366(6) . ?
C2 H2A 0.9500 . ?
C3 H3A 0.9500 . ?
C21 C19 1.514(6) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C13 C14 1.386(6) . ?
C13 H13A 0.9500 . ?
C20 C19 1.515(6) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C7 C8 1.415(6) . ?
C7 H7A 0.9500 . ?
C14 C15 1.405(6) . ?
C14 H14A 0.9500 . ?
C8 H8A 0.9500 . ?
C19 H19A 1.0000 . ?
C18 C17 1.499(7) . ?
C18 H18A 0.9800 . ?
C18 H18D 0.9800 . ?
C18 H18B 0.9800 . ?
C17 H17C 0.9900 . ?
C17 H17A 0.9900 . ?

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 N3 78.84(13) . . ?
N2 Ni1 Cl2 94.10(11) . . ?
N3 Ni1 Cl2 93.91(10) . . ?
N2 Ni1 Cl1 99.47(10) . . ?
N3 Ni1 Cl1 168.66(10) . . ?
Cl2 Ni1 Cl1 97.40(5) . . ?
N2 Ni1 Cl1 92.79(10) . 3_655 ?
N3 Ni1 Cl1 86.33(10) . 3_655 ?
Cl2 Ni1 Cl1 173.01(5) . 3_655 ?
Cl1 Ni1 Cl1 82.55(5) . 3_655 ?
Ni1 Cl1 Ni1 97.45(5) . 3_655 ?
C1 N3 C5 120.4(3) . . ?
C1 N3 Ni1 116.9(3) . . ?
C5 N3 Ni1 122.6(3) . . ?
C9 O1 C17 115.5(3) . . ?
C3 C4 C6 124.3(4) . . ?
C3 C4 C5 116.4(4) . . ?
C6 C4 C5 119.2(4) . . ?
C7 C6 C4 119.4(4) . . ?
C7 C6 H6A 120.3 . . ?
C4 C6 H6A 120.3 . . ?
C12 C11 C10 115.9(4) . . ?
C12 C11 H11A 122.1 . . ?
C10 C11 H11A 122.1 . . ?
C16 N1 C15 106.2(3) . . ?
C16 N1 C19 127.8(3) . . ?
C15 N1 C19 125.7(3) . . ?
N3 C5 C4 121.9(4) . . ?
N3 C5 C9 118.6(4) . . ?
C4 C5 C9 119.6(4) . . ?
C11 C12 C13 123.1(4) . . ?
C11 C12 Cl3 117.6(3) . . ?
C13 C12 Cl3 119.3(3) . . ?
O1 C9 C8 125.1(4) . . ?
O1 C9 C5 115.4(4) . . ?
C8 C9 C5 119.5(4) . . ?
N2 C16 N1 111.8(4) . . ?
N2 C16 C1 117.1(4) . . ?
N1 C16 C1 131.0(4) . . ?
N3 C1 C2 120.9(4) . . ?
N3 C1 C16 111.2(3) . . ?
C2 C1 C16 127.6(4) . . ?
C16 N2 C10 106.7(3) . . ?
C16 N2 Ni1 114.5(3) . . ?
C10 N2 Ni1 138.3(3) . . ?
N2 C10 C11 128.2(4) . . ?
N2 C10 C15 109.3(4) . . ?
C11 C10 C15 122.4(4) . . ?
C3 C2 C1 118.8(4) . . ?
C3 C2 H2A 120.6 . . ?
C1 C2 H2A 120.6 . . ?
C2 C3 C4 121.5(4) . . ?
C2 C3 H3A 119.2 . . ?
C4 C3 H3A 119.2 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C14 C13 C12 121.1(4) . . ?
C14 C13 H13A 119.5 . . ?
C12 C13 H13A 119.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C6 C7 C8 122.1(4) . . ?
C6 C7 H7A 118.9 . . ?
C8 C7 H7A 118.9 . . ?
C13 C14 C15 117.1(4) . . ?
C13 C14 H14A 121.4 . . ?
C15 C14 H14A 121.4 . . ?
C9 C8 C7 120.1(4) . . ?
C9 C8 H8A 119.9 . . ?
C7 C8 H8A 119.9 . . ?
N1 C15 C10 105.9(4) . . ?
N1 C15 C14 133.7(4) . . ?
C10 C15 C14 120.4(4) . . ?
N1 C19 C21 111.4(4) . . ?
N1 C19 C20 110.5(4) . . ?
C21 C19 C20 112.5(4) . . ?
N1 C19 H19A 107.4 . . ?
C21 C19 H19A 107.4 . . ?
C20 C19 H19A 107.4 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18D 109.5 . . ?
H18A C18 H18D 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18D C18 H18B 109.5 . . ?
O1 C17 C18 108.8(4) . . ?
O1 C17 H17C 109.9 . . ?
C18 C17 H17C 109.9 . . ?
O1 C17 H17A 109.9 . . ?
C18 C17 H17A 109.9 . . ?
H17C C17 H17A 108.3 . . ?

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 Cl1 Ni1 91.61(11) . . . 3_655 ?
N3 Ni1 Cl1 Ni1 11.2(5) . . . 3_655 ?
Cl2 Ni1 Cl1 Ni1 -172.95(5) . . . 3_655 ?
Cl1 Ni1 Cl1 Ni1 0.0 3_655 . . 3_655 ?
N2 Ni1 N3 C1 -4.7(3) . . . . ?
Cl2 Ni1 N3 C1 -98.1(3) . . . . ?
Cl1 Ni1 N3 C1 77.7(6) . . . . ?
Cl1 Ni1 N3 C1 88.9(3) 3_655 . . . ?
N2 Ni1 N3 C5 170.4(3) . . . . ?
Cl2 Ni1 N3 C5 77.0(3) . . . . ?
Cl1 Ni1 N3 C5 -107.1(5) . . . . ?
Cl1 Ni1 N3 C5 -96.0(3) 3_655 . . . ?
C3 C4 C6 C7 179.6(4) . . . . ?
C5 C4 C6 C7 0.7(6) . . . . ?
C1 N3 C5 C4 1.1(6) . . . . ?
Ni1 N3 C5 C4 -173.9(3) . . . . ?
C1 N3 C5 C9 -179.0(4) . . . . ?
Ni1 N3 C5 C9 6.0(5) . . . . ?
C3 C4 C5 N3 -0.8(6) . . . . ?
C6 C4 C5 N3 178.2(4) . . . . ?
C3 C4 C5 C9 179.3(4) . . . . ?
C6 C4 C5 C9 -1.7(6) . . . . ?
C10 C11 C12 C13 1.6(7) . . . . ?
C10 C11 C12 Cl3 -175.6(3) . . . . ?
C17 O1 C9 C8 14.3(6) . . . . ?
C17 O1 C9 C5 -166.2(4) . . . . ?
N3 C5 C9 O1 1.3(6) . . . . ?
C4 C5 C9 O1 -178.8(4) . . . . ?
N3 C5 C9 C8 -179.2(4) . . . . ?
C4 C5 C9 C8 0.7(6) . . . . ?
C15 N1 C16 N2 2.5(5) . . . . ?
C19 N1 C16 N2 -171.1(4) . . . . ?
C15 N1 C16 C1 -172.1(4) . . . . ?
C19 N1 C16 C1 14.3(7) . . . . ?
C5 N3 C1 C2 -1.5(6) . . . . ?
Ni1 N3 C1 C2 173.7(3) . . . . ?
C5 N3 C1 C16 -176.2(3) . . . . ?
Ni1 N3 C1 C16 -0.9(4) . . . . ?
N2 C16 C1 N3 9.7(5) . . . . ?
N1 C16 C1 N3 -175.9(4) . . . . ?
N2 C16 C1 C2 -164.5(4) . . . . ?
N1 C16 C1 C2 9.9(7) . . . . ?
N1 C16 N2 C10 -2.9(5) . . . . ?
C1 C16 N2 C10 172.6(3) . . . . ?
N1 C16 N2 Ni1 170.7(3) . . . . ?
C1 C16 N2 Ni1 -13.9(5) . . . . ?
N3 Ni1 N2 C16 10.0(3) . . . . ?
Cl2 Ni1 N2 C16 103.2(3) . . . . ?
Cl1 Ni1 N2 C16 -158.6(3) . . . . ?
Cl1 Ni1 N2 C16 -75.7(3) 3_655 . . . ?
N3 Ni1 N2 C10 -179.3(4) . . . . ?
Cl2 Ni1 N2 C10 -86.1(4) . . . . ?
Cl1 Ni1 N2 C10 12.1(4) . . . . ?
Cl1 Ni1 N2 C10 95.0(4) 3_655 . . . ?
C16 N2 C10 C11 -175.7(4) . . . . ?
Ni1 N2 C10 C11 13.1(7) . . . . ?
C16 N2 C10 C15 2.1(5) . . . . ?
Ni1 N2 C10 C15 -169.0(3) . . . . ?
C12 C11 C10 N2 178.2(4) . . . . ?
C12 C11 C10 C15 0.6(6) . . . . ?
N3 C1 C2 C3 1.7(6) . . . . ?
C16 C1 C2 C3 175.4(4) . . . . ?
C1 C2 C3 C4 -1.4(7) . . . . ?
C6 C4 C3 C2 -177.9(4) . . . . ?
C5 C4 C3 C2 1.0(6) . . . . ?
C11 C12 C13 C14 -2.0(7) . . . . ?
Cl3 C12 C13 C14 175.1(4) . . . . ?
C4 C6 C7 C8 1.3(7) . . . . ?
C12 C13 C14 C15 0.2(7) . . . . ?
O1 C9 C8 C7 -179.3(4) . . . . ?
C5 C9 C8 C7 1.3(7) . . . . ?
C6 C7 C8 C9 -2.3(7) . . . . ?
C16 N1 C15 C10 -1.1(4) . . . . ?
C19 N1 C15 C10 172.7(4) . . . . ?
C16 N1 C15 C14 178.6(5) . . . . ?
C19 N1 C15 C14 -7.7(8) . . . . ?
N2 C10 C15 N1 -0.6(5) . . . . ?
C11 C10 C15 N1 177.4(4) . . . . ?
N2 C10 C15 C14 179.7(4) . . . . ?
C11 C10 C15 C14 -2.3(7) . . . . ?
C13 C14 C15 N1 -177.8(5) . . . . ?
C13 C14 C15 C10 1.8(7) . . . . ?
C16 N1 C19 C21 123.5(4) . . . . ?
C15 N1 C19 C21 -48.9(6) . . . . ?
C16 N1 C19 C20 -110.7(5) . . . . ?
C15 N1 C19 C20 76.9(5) . . . . ?
C9 O1 C17 C18 167.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.44
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.776
_refine_diff_density_rms         0.174
#==End

data_C11
_database_code_depnum_ccdc_archive 'CCDC 795583'
#TrackingRef '- CIF.CIF'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 Br2 Cl N3 Ni O'
_chemical_formula_weight         570.31

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'
Br Br -0.2901 2.4595 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3745(19)
_cell_length_b                   9.859(2)
_cell_length_c                   11.024(2)
_cell_angle_alpha                87.77(3)
_cell_angle_beta                 84.15(3)
_cell_angle_gamma                86.62(3)
_cell_volume                     1011.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      1.86
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.873
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             564
_exptl_absorpt_coefficient_mu    5.059
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.2308
_exptl_absorpt_correction_T_max  0.7511

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            12363
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0414
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4608
_reflns_number_gt                4279
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Siemens SMART'
_computing_cell_refinement       'Siemens SMART & SAINT'
_computing_data_reduction        'Siemens XPREP'
_computing_structure_solution    'Siemens SHELXTL'
_computing_structure_refinement  'Siemens SHELXTL'
_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^)+(0.0211P)^2^+1.2360P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4608
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_ref          0.0399
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0794
_refine_ls_wR_factor_gt          0.0733
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.140
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.18996(3) 0.17193(3) 0.54935(3) 0.02807(9) Uani 1 1 d . . .
Br2 Br 0.21762(4) 0.07834(3) 0.91415(3) 0.03209(10) Uani 1 1 d . . .
Ni1 Ni 0.25883(4) 0.23124(4) 0.74451(3) 0.02157(10) Uani 1 1 d . . .
Cl1 Cl -0.39827(8) 0.25874(8) 0.96466(8) 0.03081(18) Uani 1 1 d . . .
O1 O 0.4870(2) 0.1431(2) 0.6898(2) 0.0273(5) Uani 1 1 d . . .
C20 C 0.0448(4) 0.8360(3) 0.7139(3) 0.0352(8) Uani 1 1 d . . .
H20A H 0.0568 0.9329 0.7238 0.053 Uiso 1 1 calc R . .
H20B H -0.0558 0.8220 0.7038 0.053 Uiso 1 1 calc R . .
H20C H 0.1058 0.8048 0.6416 0.053 Uiso 1 1 calc R . .
N2 N 0.1142(3) 0.3861(2) 0.7871(2) 0.0212(5) Uani 1 1 d . . .
N3 N 0.3815(3) 0.3906(3) 0.7086(2) 0.0221(5) Uani 1 1 d . . .
N1 N 0.0725(3) 0.6088(2) 0.8170(2) 0.0224(5) Uani 1 1 d . . .
C11 C -0.1302(3) 0.3134(3) 0.8708(3) 0.0229(6) Uani 1 1 d . . .
H11A H -0.1127 0.2187 0.8594 0.027 Uiso 1 1 calc R . .
C10 C -0.0249(3) 0.4068(3) 0.8378(3) 0.0207(6) Uani 1 1 d . . .
C16 C 0.1691(3) 0.5079(3) 0.7750(3) 0.0215(6) Uani 1 1 d . . .
C9 C 0.5820(3) 0.2388(3) 0.6511(3) 0.0239(6) Uani 1 1 d . . .
C2 C 0.3956(3) 0.6319(3) 0.6900(3) 0.0259(7) Uani 1 1 d . . .
H2A H 0.3499 0.7199 0.6999 0.031 Uiso 1 1 calc R . .
C12 C -0.2602(3) 0.3676(3) 0.9208(3) 0.0237(6) Uani 1 1 d . . .
C14 C -0.1856(3) 0.5988(3) 0.9072(3) 0.0249(7) Uani 1 1 d . . .
H14A H -0.2038 0.6933 0.9197 0.030 Uiso 1 1 calc R . .
C4 C 0.6052(3) 0.4868(3) 0.6286(3) 0.0240(6) Uani 1 1 d . . .
C7 C 0.8066(3) 0.3309(4) 0.5730(3) 0.0302(7) Uani 1 1 d . . .
H7A H 0.9047 0.3153 0.5431 0.036 Uiso 1 1 calc R . .
C15 C -0.0531(3) 0.5462(3) 0.8560(3) 0.0220(6) Uani 1 1 d . . .
C6 C 0.7505(3) 0.4619(4) 0.5828(3) 0.0285(7) Uani 1 1 d . . .
H6A H 0.8089 0.5358 0.5589 0.034 Uiso 1 1 calc R . .
C5 C 0.5212(3) 0.3743(3) 0.6630(3) 0.0218(6) Uani 1 1 d . . .
C1 C 0.3199(3) 0.5151(3) 0.7242(3) 0.0211(6) Uani 1 1 d . . .
C19 C 0.0878(3) 0.7560(3) 0.8256(3) 0.0243(6) Uani 1 1 d . . .
H19A H 0.1889 0.7721 0.8364 0.029 Uiso 1 1 calc R . .
H19B H 0.0273 0.7893 0.8985 0.029 Uiso 1 1 calc R . .
C8 C 0.7227(3) 0.2183(3) 0.6061(3) 0.0280(7) Uani 1 1 d . . .
H8A H 0.7640 0.1284 0.5972 0.034 Uiso 1 1 calc R . .
C13 C -0.2888(3) 0.5069(3) 0.9388(3) 0.0271(7) Uani 1 1 d . . .
H13A H -0.3812 0.5384 0.9735 0.033 Uiso 1 1 calc R . .
C17 C 0.5313(4) 0.0002(3) 0.6804(3) 0.0299(7) Uani 1 1 d . . .
H17A H 0.5929 -0.0137 0.6030 0.036 Uiso 1 1 calc R . .
H17B H 0.4454 -0.0533 0.6788 0.036 Uiso 1 1 calc R . .
C3 C 0.5361(4) 0.6171(3) 0.6422(3) 0.0273(7) Uani 1 1 d . . .
H3A H 0.5875 0.6954 0.6179 0.033 Uiso 1 1 calc R . .
C18 C 0.6125(4) -0.0502(4) 0.7853(3) 0.0371(8) Uani 1 1 d . . .
H18A H 0.6408 -0.1469 0.7762 0.056 Uiso 1 1 calc R . .
H18B H 0.5512 -0.0381 0.8621 0.056 Uiso 1 1 calc R . .
H18C H 0.6985 0.0014 0.7863 0.056 Uiso 1 1 calc R . .

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
Br1 0.02858(17) 0.02990(18) 0.02571(17) -0.00485(13) -0.00303(13) 0.00167(13)
Br2 0.0449(2) 0.02318(17) 0.02652(17) 0.00213(13) -0.00001(14) 0.00370(14)
Ni1 0.0230(2) 0.01723(19) 0.0237(2) -0.00139(15) -0.00071(15) 0.00248(15)
Cl1 0.0263(4) 0.0276(4) 0.0373(4) -0.0006(3) 0.0032(3) -0.0023(3)
O1 0.0228(11) 0.0190(11) 0.0390(13) -0.0020(9) -0.0005(10) 0.0046(9)
C20 0.050(2) 0.0222(17) 0.0347(19) 0.0020(14) -0.0120(16) 0.0021(15)
N2 0.0235(13) 0.0183(12) 0.0214(13) -0.0020(10) -0.0017(10) 0.0015(10)
N3 0.0239(13) 0.0210(13) 0.0217(13) -0.0037(10) -0.0051(10) 0.0028(10)
N1 0.0253(13) 0.0178(12) 0.0238(13) -0.0037(10) -0.0030(10) 0.0052(10)
C11 0.0287(16) 0.0192(15) 0.0208(15) -0.0026(11) -0.0041(12) 0.0024(12)
C10 0.0217(14) 0.0200(14) 0.0199(14) -0.0034(11) -0.0015(11) 0.0030(11)
C16 0.0258(15) 0.0186(14) 0.0203(14) -0.0014(11) -0.0039(12) 0.0014(12)
C9 0.0268(16) 0.0242(16) 0.0208(15) 0.0006(12) -0.0055(12) 0.0013(12)
C2 0.0316(17) 0.0195(15) 0.0264(16) -0.0034(12) -0.0028(13) 0.0014(12)
C12 0.0224(15) 0.0254(16) 0.0234(15) 0.0005(12) -0.0029(12) -0.0020(12)
C14 0.0272(16) 0.0211(15) 0.0262(16) -0.0045(12) -0.0034(13) 0.0043(12)
C4 0.0258(16) 0.0293(17) 0.0176(14) -0.0001(12) -0.0040(12) -0.0038(13)
C7 0.0209(16) 0.042(2) 0.0269(17) -0.0005(14) -0.0023(13) 0.0019(14)
C15 0.0233(15) 0.0219(15) 0.0209(15) -0.0020(12) -0.0034(12) 0.0000(12)
C6 0.0247(16) 0.0364(19) 0.0248(16) 0.0004(14) -0.0030(13) -0.0039(14)
C5 0.0223(15) 0.0233(15) 0.0195(14) 0.0001(11) -0.0039(12) 0.0029(12)
C1 0.0239(15) 0.0196(14) 0.0195(14) -0.0005(11) -0.0022(12) 0.0008(12)
C19 0.0299(16) 0.0180(15) 0.0255(16) -0.0060(12) -0.0040(13) 0.0000(12)
C8 0.0277(17) 0.0322(18) 0.0235(16) -0.0030(13) -0.0040(13) 0.0067(13)
C13 0.0250(16) 0.0278(17) 0.0273(16) -0.0039(13) 0.0010(13) 0.0047(13)
C17 0.0303(17) 0.0202(16) 0.0391(19) -0.0052(13) -0.0053(14) 0.0054(13)
C3 0.0317(17) 0.0252(16) 0.0258(16) 0.0009(13) -0.0044(13) -0.0064(13)
C18 0.043(2) 0.0251(18) 0.043(2) 0.0002(15) -0.0082(17) 0.0075(15)

_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
Br1 Ni1 2.4110(7) . ?
Br2 Ni1 2.3708(9) . ?
Ni1 N3 2.005(3) . ?
Ni1 N2 2.018(2) . ?
Ni1 O1 2.292(2) . ?
Cl1 C12 1.748(3) . ?
O1 C9 1.362(4) . ?
O1 C17 1.450(4) . ?
C20 C19 1.513(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
N2 C16 1.331(4) . ?
N2 C10 1.372(4) . ?
N3 C1 1.335(4) . ?
N3 C5 1.358(4) . ?
N1 C16 1.367(4) . ?
N1 C15 1.384(4) . ?
N1 C19 1.475(4) . ?
C11 C12 1.372(4) . ?
C11 C10 1.401(4) . ?
C11 H11A 0.9500 . ?
C10 C15 1.402(4) . ?
C16 C1 1.471(4) . ?
C9 C8 1.368(4) . ?
C9 C5 1.426(4) . ?
C2 C3 1.369(5) . ?
C2 C1 1.407(4) . ?
C2 H2A 0.9500 . ?
C12 C13 1.402(4) . ?
C14 C13 1.374(5) . ?
C14 C15 1.391(4) . ?
C14 H14A 0.9500 . ?
C4 C3 1.411(4) . ?
C4 C6 1.414(4) . ?
C4 C5 1.415(4) . ?
C7 C6 1.370(5) . ?
C7 C8 1.414(5) . ?
C7 H7A 0.9500 . ?
C6 H6A 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C8 H8A 0.9500 . ?
C13 H13A 0.9500 . ?
C17 C18 1.502(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C3 H3A 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Ni1 N2 79.36(10) . . ?
N3 Ni1 O1 73.69(9) . . ?
N2 Ni1 O1 152.84(9) . . ?
N3 Ni1 Br2 134.28(8) . . ?
N2 Ni1 Br2 102.15(8) . . ?
O1 Ni1 Br2 94.34(7) . . ?
N3 Ni1 Br1 105.09(8) . . ?
N2 Ni1 Br1 100.78(8) . . ?
O1 Ni1 Br1 89.56(6) . . ?
Br2 Ni1 Br1 119.06(3) . . ?
C9 O1 C17 119.5(2) . . ?
C9 O1 Ni1 113.80(17) . . ?
C17 O1 Ni1 126.27(19) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 N2 C10 106.4(2) . . ?
C16 N2 Ni1 113.7(2) . . ?
C10 N2 Ni1 139.5(2) . . ?
C1 N3 C5 120.2(3) . . ?
C1 N3 Ni1 118.2(2) . . ?
C5 N3 Ni1 121.5(2) . . ?
C16 N1 C15 106.1(2) . . ?
C16 N1 C19 130.8(3) . . ?
C15 N1 C19 123.0(2) . . ?
C12 C11 C10 115.7(3) . . ?
C12 C11 H11A 122.1 . . ?
C10 C11 H11A 122.1 . . ?
N2 C10 C11 130.1(3) . . ?
N2 C10 C15 108.8(3) . . ?
C11 C10 C15 121.1(3) . . ?
N2 C16 N1 112.1(3) . . ?
N2 C16 C1 117.9(3) . . ?
N1 C16 C1 129.9(3) . . ?
O1 C9 C8 127.8(3) . . ?
O1 C9 C5 112.9(3) . . ?
C8 C9 C5 119.4(3) . . ?
C3 C2 C1 119.1(3) . . ?
C3 C2 H2A 120.4 . . ?
C1 C2 H2A 120.4 . . ?
C11 C12 C13 123.3(3) . . ?
C11 C12 Cl1 119.0(2) . . ?
C13 C12 Cl1 117.7(2) . . ?
C13 C14 C15 116.5(3) . . ?
C13 C14 H14A 121.7 . . ?
C15 C14 H14A 121.7 . . ?
C3 C4 C6 124.6(3) . . ?
C3 C4 C5 116.8(3) . . ?
C6 C4 C5 118.6(3) . . ?
C6 C7 C8 121.8(3) . . ?
C6 C7 H7A 119.1 . . ?
C8 C7 H7A 119.1 . . ?
N1 C15 C14 131.2(3) . . ?
N1 C15 C10 106.6(3) . . ?
C14 C15 C10 122.2(3) . . ?
C7 C6 C4 119.7(3) . . ?
C7 C6 H6A 120.1 . . ?
C4 C6 H6A 120.1 . . ?
N3 C5 C4 121.7(3) . . ?
N3 C5 C9 117.7(3) . . ?
C4 C5 C9 120.6(3) . . ?
N3 C1 C2 121.3(3) . . ?
N3 C1 C16 110.6(3) . . ?
C2 C1 C16 128.0(3) . . ?
N1 C19 C20 112.5(3) . . ?
N1 C19 H19A 109.1 . . ?
C20 C19 H19A 109.1 . . ?
N1 C19 H19B 109.1 . . ?
C20 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
C9 C8 C7 119.9(3) . . ?
C9 C8 H8A 120.0 . . ?
C7 C8 H8A 120.0 . . ?
C14 C13 C12 121.2(3) . . ?
C14 C13 H13A 119.4 . . ?
C12 C13 H13A 119.4 . . ?
O1 C17 C18 111.6(3) . . ?
O1 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
O1 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
C2 C3 C4 120.7(3) . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 H3A 119.6 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.095
#==End