# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_14059

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H23 F N2 O2'
_chemical_formula_sum            'C25 H23 F N2 O2'
_chemical_formula_weight         402.45

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_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                   8.2975(16)
_cell_length_b                   11.260(2)
_cell_length_c                   21.170(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1977.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    764
_cell_measurement_theta_min      2.642
_cell_measurement_theta_max      23.298

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.595
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_process_details   
;
absorption correction based on 5746 reflections(SADABS);Rint 0.1032 before
correction and 0.0511 after.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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 Apex 2000 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            15528
_diffrn_reflns_av_R_equivalents  0.0906
_diffrn_reflns_av_sigmaI/netI    0.0560
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         25.99
_reflns_number_total             2232
_reflns_number_gt                1908
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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 F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0362P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ,syn
_refine_ls_number_reflns         2232
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.0819
_refine_ls_wR_factor_gt          0.0787
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.18443(19) 0.94936(13) 0.94396(7) 0.0344(4) Uani 1 1 d . . .
O1 O 0.1434(2) 0.97510(16) 0.70668(8) 0.0325(5) Uani 1 1 d . . .
O2 O 0.5371(3) 1.01739(17) 0.87939(8) 0.0378(5) Uani 1 1 d . . .
N1 N 0.2643(2) 0.96578(18) 0.80405(9) 0.0226(5) Uani 1 1 d . . .
H1 H 0.2815 1.0095 0.8378 0.027 Uiso 1 1 calc R . .
N2 N 0.1069(2) 1.15425(18) 0.84848(9) 0.0227(5) Uani 1 1 d . . .
C1 C 0.1664(3) 1.0146(2) 0.75970(11) 0.0218(6) Uani 1 1 d . . .
C2 C 0.3419(3) 0.8548(2) 0.80334(11) 0.0193(5) Uani 1 1 d . . .
C3 C 0.3102(3) 0.7703(2) 0.75732(11) 0.0225(6) Uani 1 1 d . . .
H3 H 0.2408 0.7895 0.7232 0.027 Uiso 1 1 calc R . .
C4 C 0.3781(3) 0.6588(2) 0.76046(12) 0.0267(6) Uani 1 1 d . . .
H4 H 0.3566 0.6027 0.7280 0.032 Uiso 1 1 calc R . .
C5 C 0.4773(3) 0.6277(2) 0.81032(12) 0.0272(6) Uani 1 1 d . . .
H5 H 0.5213 0.5500 0.8130 0.033 Uiso 1 1 calc R . .
C6 C 0.5112(3) 0.7111(2) 0.85609(12) 0.0247(6) Uani 1 1 d . . .
H6 H 0.5791 0.6900 0.8904 0.030 Uiso 1 1 calc R . .
C7 C 0.4483(3) 0.8248(2) 0.85301(11) 0.0212(6) Uani 1 1 d . . .
C8 C 0.5087(3) 0.9170(2) 0.89832(12) 0.0235(6) Uani 1 1 d . . .
C9 C 0.5402(3) 0.8863(2) 0.96598(11) 0.0227(6) Uani 1 1 d . . .
C10 C 0.4601(3) 0.7957(2) 0.99701(12) 0.0260(6) Uani 1 1 d . . .
H10 H 0.3885 0.7455 0.9743 0.031 Uiso 1 1 calc R . .
C11 C 0.4840(4) 0.7780(3) 1.06128(12) 0.0333(7) Uani 1 1 d . . .
H11 H 0.4279 0.7163 1.0826 0.040 Uiso 1 1 calc R . .
C12 C 0.5891(4) 0.8500(3) 1.09408(13) 0.0350(7) Uani 1 1 d . . .
H12 H 0.6057 0.8377 1.1380 0.042 Uiso 1 1 calc R . .
C13 C 0.6703(4) 0.9398(2) 1.06325(13) 0.0343(7) Uani 1 1 d . . .
H13 H 0.7435 0.9887 1.0859 0.041 Uiso 1 1 calc R . .
C14 C 0.6454(3) 0.9589(2) 0.99973(12) 0.0274(6) Uani 1 1 d . . .
H14 H 0.7001 1.0218 0.9789 0.033 Uiso 1 1 calc R . .
C15 C 0.1387(3) 1.2818(2) 0.85414(12) 0.0293(6) Uani 1 1 d . . .
H15A H 0.2054 1.2992 0.8918 0.035 Uiso 1 1 calc R . .
H15B H 0.0370 1.3274 0.8569 0.035 Uiso 1 1 calc R . .
C16 C 0.2286(3) 1.3106(2) 0.79414(13) 0.0333(7) Uani 1 1 d . . .
H16A H 0.3426 1.2851 0.7967 0.040 Uiso 1 1 calc R . .
H16B H 0.2244 1.3967 0.7847 0.040 Uiso 1 1 calc R . .
C17 C 0.1366(3) 1.2389(2) 0.74504(11) 0.0275(6) Uani 1 1 d . . .
H17A H 0.2073 1.2171 0.7092 0.033 Uiso 1 1 calc R . .
H17B H 0.0432 1.2843 0.7287 0.033 Uiso 1 1 calc R . .
C18 C 0.0805(3) 1.1274(2) 0.78118(11) 0.0237(6) Uani 1 1 d . . .
H18 H -0.0378 1.1171 0.7740 0.028 Uiso 1 1 calc R . .
C19 C -0.0226(3) 1.1126(2) 0.88998(11) 0.0262(6) Uani 1 1 d . . .
H19A H -0.0498 1.0294 0.8791 0.031 Uiso 1 1 calc R . .
H19B H -0.1199 1.1618 0.8831 0.031 Uiso 1 1 calc R . .
C20 C 0.0257(3) 1.1192(2) 0.95802(11) 0.0241(6) Uani 1 1 d . . .
C21 C 0.1315(3) 1.0365(2) 0.98319(11) 0.0243(6) Uani 1 1 d . . .
C22 C 0.1837(3) 1.0371(2) 1.04461(12) 0.0289(6) Uani 1 1 d . . .
H22 H 0.2559 0.9782 1.0598 0.035 Uiso 1 1 calc R . .
C23 C 0.1277(3) 1.1265(2) 1.08388(12) 0.0314(7) Uani 1 1 d . . .
H23 H 0.1612 1.1290 1.1268 0.038 Uiso 1 1 calc R . .
C24 C 0.0240(4) 1.2115(3) 1.06119(12) 0.0341(7) Uani 1 1 d . . .
H24 H -0.0131 1.2730 1.0883 0.041 Uiso 1 1 calc R . .
C25 C -0.0264(4) 1.2076(2) 0.99902(12) 0.0304(7) Uani 1 1 d . . .
H25 H -0.0984 1.2668 0.9839 0.036 Uiso 1 1 calc R . .


_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
F1 C21 1.359(3) . ?
O1 C1 1.222(3) . ?
O2 C8 1.222(3) . ?
N1 C1 1.358(3) . ?
N1 C2 1.406(3) . ?
N1 H1 0.8800 . ?
N2 C19 1.465(3) . ?
N2 C15 1.465(3) . ?
N2 C18 1.473(3) . ?
C1 C18 1.526(3) . ?
C2 C3 1.387(3) . ?
C2 C7 1.414(3) . ?
C3 C4 1.377(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.378(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.385(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.500(3) . ?
C8 C9 1.497(3) . ?
C9 C10 1.383(3) . ?
C9 C14 1.394(3) . ?
C10 C11 1.389(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.378(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.377(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.508(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.522(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.542(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18 1.0000 . ?
C19 C20 1.497(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.386(4) . ?
C20 C25 1.390(3) . ?
C21 C22 1.371(3) . ?
C22 C23 1.385(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.374(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.382(4) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?

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
C1 N1 C2 128.8(2) . . ?
C1 N1 H1 115.6 . . ?
C2 N1 H1 115.6 . . ?
C19 N2 C15 113.4(2) . . ?
C19 N2 C18 113.9(2) . . ?
C15 N2 C18 107.87(19) . . ?
O1 C1 N1 125.5(2) . . ?
O1 C1 C18 120.3(2) . . ?
N1 C1 C18 114.2(2) . . ?
C3 C2 N1 122.0(2) . . ?
C3 C2 C7 118.5(2) . . ?
N1 C2 C7 119.4(2) . . ?
C4 C3 C2 120.9(2) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 120.7(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 119.0(2) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C7 121.3(2) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C6 C7 C2 119.4(2) . . ?
C6 C7 C8 119.0(2) . . ?
C2 C7 C8 121.3(2) . . ?
O2 C8 C9 119.6(2) . . ?
O2 C8 C7 119.7(2) . . ?
C9 C8 C7 120.7(2) . . ?
C10 C9 C14 119.4(2) . . ?
C10 C9 C8 122.8(2) . . ?
C14 C9 C8 117.6(2) . . ?
C9 C10 C11 120.1(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.1(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 120.2(3) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C9 120.2(3) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
N2 C15 C16 103.4(2) . . ?
N2 C15 H15A 111.1 . . ?
C16 C15 H15A 111.1 . . ?
N2 C15 H15B 111.1 . . ?
C16 C15 H15B 111.1 . . ?
H15A C15 H15B 109.1 . . ?
C15 C16 C17 102.3(2) . . ?
C15 C16 H16A 111.3 . . ?
C17 C16 H16A 111.3 . . ?
C15 C16 H16B 111.3 . . ?
C17 C16 H16B 111.3 . . ?
H16A C16 H16B 109.2 . . ?
C16 C17 C18 104.1(2) . . ?
C16 C17 H17A 110.9 . . ?
C18 C17 H17A 110.9 . . ?
C16 C17 H17B 110.9 . . ?
C18 C17 H17B 110.9 . . ?
H17A C17 H17B 108.9 . . ?
N2 C18 C1 112.9(2) . . ?
N2 C18 C17 105.6(2) . . ?
C1 C18 C17 112.9(2) . . ?
N2 C18 H18 108.4 . . ?
C1 C18 H18 108.4 . . ?
C17 C18 H18 108.4 . . ?
N2 C19 C20 111.4(2) . . ?
N2 C19 H19A 109.3 . . ?
C20 C19 H19A 109.3 . . ?
N2 C19 H19B 109.3 . . ?
C20 C19 H19B 109.3 . . ?
H19A C19 H19B 108.0 . . ?
C21 C20 C25 116.0(2) . . ?
C21 C20 C19 120.4(2) . . ?
C25 C20 C19 123.6(2) . . ?
F1 C21 C22 118.8(2) . . ?
F1 C21 C20 117.1(2) . . ?
C22 C21 C20 124.2(2) . . ?
C21 C22 C23 117.8(3) . . ?
C21 C22 H22 121.1 . . ?
C23 C22 H22 121.1 . . ?
C24 C23 C22 120.4(3) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 120.0(3) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 C20 121.6(3) . . ?
C24 C25 H25 119.2 . . ?
C20 C25 H25 119.2 . . ?

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
C2 N1 C1 O1 -9.4(4) . . . . ?
C2 N1 C1 C18 170.0(2) . . . . ?
C1 N1 C2 C3 -8.4(4) . . . . ?
C1 N1 C2 C7 175.6(2) . . . . ?
N1 C2 C3 C4 -174.8(2) . . . . ?
C7 C2 C3 C4 1.3(4) . . . . ?
C2 C3 C4 C5 1.2(4) . . . . ?
C3 C4 C5 C6 -1.8(4) . . . . ?
C4 C5 C6 C7 -0.1(4) . . . . ?
C5 C6 C7 C2 2.6(4) . . . . ?
C5 C6 C7 C8 -170.8(2) . . . . ?
C3 C2 C7 C6 -3.1(3) . . . . ?
N1 C2 C7 C6 173.0(2) . . . . ?
C3 C2 C7 C8 170.1(2) . . . . ?
N1 C2 C7 C8 -13.8(3) . . . . ?
C6 C7 C8 O2 137.3(3) . . . . ?
C2 C7 C8 O2 -36.0(4) . . . . ?
C6 C7 C8 C9 -40.5(3) . . . . ?
C2 C7 C8 C9 146.3(2) . . . . ?
O2 C8 C9 C10 155.1(3) . . . . ?
C7 C8 C9 C10 -27.2(4) . . . . ?
O2 C8 C9 C14 -19.7(4) . . . . ?
C7 C8 C9 C14 158.1(2) . . . . ?
C14 C9 C10 C11 0.3(4) . . . . ?
C8 C9 C10 C11 -174.3(2) . . . . ?
C9 C10 C11 C12 -0.7(4) . . . . ?
C10 C11 C12 C13 0.2(4) . . . . ?
C11 C12 C13 C14 0.7(4) . . . . ?
C12 C13 C14 C9 -1.1(4) . . . . ?
C10 C9 C14 C13 0.6(4) . . . . ?
C8 C9 C14 C13 175.5(2) . . . . ?
C19 N2 C15 C16 -161.1(2) . . . . ?
C18 N2 C15 C16 -34.0(3) . . . . ?
N2 C15 C16 C17 41.2(3) . . . . ?
C15 C16 C17 C18 -33.0(3) . . . . ?
C19 N2 C18 C1 -96.6(2) . . . . ?
C15 N2 C18 C1 136.6(2) . . . . ?
C19 N2 C18 C17 139.6(2) . . . . ?
C15 N2 C18 C17 12.8(3) . . . . ?
O1 C1 C18 N2 173.1(2) . . . . ?
N1 C1 C18 N2 -6.3(3) . . . . ?
O1 C1 C18 C17 -67.2(3) . . . . ?
N1 C1 C18 C17 113.3(2) . . . . ?
C16 C17 C18 N2 13.1(3) . . . . ?
C16 C17 C18 C1 -110.7(2) . . . . ?
C15 N2 C19 C20 -68.0(3) . . . . ?
C18 N2 C19 C20 168.2(2) . . . . ?
N2 C19 C20 C21 -75.3(3) . . . . ?
N2 C19 C20 C25 102.8(3) . . . . ?
C25 C20 C21 F1 -179.9(2) . . . . ?
C19 C20 C21 F1 -1.6(4) . . . . ?
C25 C20 C21 C22 0.8(4) . . . . ?
C19 C20 C21 C22 179.0(2) . . . . ?
F1 C21 C22 C23 -179.7(2) . . . . ?
C20 C21 C22 C23 -0.4(4) . . . . ?
C21 C22 C23 C24 -0.4(4) . . . . ?
C22 C23 C24 C25 0.6(4) . . . . ?
C23 C24 C25 C20 -0.2(4) . . . . ?
C21 C20 C25 C24 -0.5(4) . . . . ?
C19 C20 C25 C24 -178.7(3) . . . . ?

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
N1 H1 N2 0.88 2.19 2.663(3) 113.1 .
N1 H1 O2 0.88 2.30 2.830(3) 118.8 .
N1 H1 F1 0.88 2.48 3.041(3) 122.0 .

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.043

_database_code_depnum_ccdc_archive 'CCDC 1020152'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_13078

_vrf_RINTA01_I                   
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: ...The crystals were not the best and hence the data was weak.
;
_vrf_PLAT020_I                   
;
PROBLEM: The value of Rint is greater than 0.12 .........      0.342      
RESPONSE: ...The crystals were not the best and hence the data was weak.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H24 F N3 Ni O3, C H2 Cl2'
_chemical_formula_sum            'C28 H26 Cl2 F N3 Ni O3'
_chemical_formula_weight         601.13

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'
F F 0.0171 0.0103 '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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_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                   9.380(7)
_cell_length_b                   16.703(12)
_cell_length_c                   16.766(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2627(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    882
_cell_measurement_theta_min      2.430
_cell_measurement_theta_max      23.635

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1240
_exptl_absorpt_coefficient_mu    0.986
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.300
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_process_details   
;
absorption correction based on 2613 reflections(SADABS);Rint 0.1365 before
correction and 0.0871 after.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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 Apex 2000 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            20992
_diffrn_reflns_av_R_equivalents  0.3423
_diffrn_reflns_av_sigmaI/netI    0.2832
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         26.00
_reflns_number_total             5142
_reflns_number_gt                2102
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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 F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0478P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(4)
_chemical_absolute_configuration ,syn
_refine_ls_number_reflns         5142
_refine_ls_number_parameters     344
_refine_ls_number_restraints     330
_refine_ls_R_factor_all          0.1947
_refine_ls_R_factor_gt           0.0879
_refine_ls_wR_factor_ref         0.2024
_refine_ls_wR_factor_gt          0.1596
_refine_ls_goodness_of_fit_ref   0.868
_refine_ls_restrained_S_all      0.844
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.24501(17) 0.28772(6) 0.82080(7) 0.0394(4) Uani 1 1 d U . .
F1 F 0.5621(9) 0.2482(3) 0.5898(4) 0.076(2) Uani 1 1 d U . .
O1 O 0.1750(8) 0.1672(3) 0.6259(4) 0.054(2) Uani 1 1 d U . .
O2 O 0.3317(8) 0.3091(3) 0.9167(4) 0.0452(17) Uani 1 1 d U . .
O3 O 0.2925(8) 0.3636(3) 1.0364(4) 0.048(2) Uani 1 1 d U . .
N1 N 0.4080(9) 0.2302(4) 0.7849(5) 0.0380(18) Uani 1 1 d U . .
N2 N 0.1654(8) 0.2657(4) 0.7238(4) 0.0345(17) Uani 1 1 d U . .
N3 N 0.0878(10) 0.3388(4) 0.8593(4) 0.0359(18) Uani 1 1 d U . .
C1 C 0.4745(12) 0.1802(5) 0.8468(6) 0.050(3) Uani 1 1 d U . .
H1A H 0.4873 0.2104 0.8971 0.060 Uiso 1 1 calc R . .
H1B H 0.5679 0.1593 0.8290 0.060 Uiso 1 1 calc R . .
C2 C 0.3658(12) 0.1132(5) 0.8564(6) 0.052(3) Uani 1 1 d U . .
H2A H 0.4085 0.0668 0.8843 0.062 Uiso 1 1 calc R . .
H2B H 0.2820 0.1319 0.8871 0.062 Uiso 1 1 calc R . .
C3 C 0.3245(12) 0.0914(5) 0.7732(6) 0.049(3) Uani 1 1 d U . .
H3A H 0.2227 0.0761 0.7701 0.058 Uiso 1 1 calc R . .
H3B H 0.3836 0.0468 0.7527 0.058 Uiso 1 1 calc R . .
C4 C 0.3543(12) 0.1718(5) 0.7251(6) 0.044(2) Uani 1 1 d U . .
H4 H 0.4299 0.1618 0.6842 0.053 Uiso 1 1 calc R . .
C5 C 0.2227(12) 0.2008(5) 0.6847(6) 0.043(2) Uani 1 1 d U . .
C6 C 0.0494(11) 0.3074(4) 0.6912(5) 0.031(2) Uani 1 1 d U . .
C7 C 0.0346(13) 0.3112(5) 0.6059(6) 0.041(3) Uani 1 1 d U . .
H7 H 0.1018 0.2860 0.5717 0.049 Uiso 1 1 calc R . .
C8 C -0.0772(12) 0.3515(5) 0.5762(6) 0.045(3) Uani 1 1 d U . .
H8 H -0.0870 0.3536 0.5199 0.054 Uiso 1 1 calc R . .
C9 C -0.1774(13) 0.3896(5) 0.6206(6) 0.047(3) Uani 1 1 d U . .
H9 H -0.2549 0.4164 0.5959 0.056 Uiso 1 1 calc R . .
C10 C -0.1640(12) 0.3883(5) 0.7024(6) 0.044(2) Uani 1 1 d U . .
H10 H -0.2330 0.4142 0.7348 0.053 Uiso 1 1 calc R . .
C11 C -0.0471(11) 0.3481(5) 0.7382(6) 0.037(2) Uani 1 1 d U . .
C12 C -0.0306(11) 0.3576(4) 0.8240(6) 0.0325(18) Uani 1 1 d U . .
C13 C -0.1479(12) 0.3872(5) 0.8712(6) 0.039(2) Uani 1 1 d U . .
C14 C -0.1768(13) 0.4690(5) 0.8820(6) 0.052(3) Uani 1 1 d U . .
H14 H -0.1167 0.5067 0.8561 0.063 Uiso 1 1 calc R . .
C15 C -0.2848(14) 0.4968(6) 0.9270(6) 0.059(4) Uani 1 1 d U . .
H15 H -0.3007 0.5527 0.9319 0.070 Uiso 1 1 calc R . .
C16 C -0.3732(12) 0.4424(5) 0.9662(6) 0.047(3) Uani 1 1 d U . .
H16 H -0.4498 0.4604 0.9986 0.056 Uiso 1 1 calc R . .
C17 C -0.3462(12) 0.3623(5) 0.9565(6) 0.050(3) Uani 1 1 d U . .
H17 H -0.4061 0.3248 0.9828 0.060 Uiso 1 1 calc R . .
C18 C -0.2382(13) 0.3348(5) 0.9115(5) 0.045(3) Uani 1 1 d U . .
H18 H -0.2233 0.2787 0.9070 0.054 Uiso 1 1 calc R . .
C19 C 0.1040(12) 0.3545(5) 0.9457(6) 0.042(2) Uani 1 1 d U . .
H19A H 0.0717 0.4096 0.9577 0.050 Uiso 1 1 calc R . .
H19B H 0.0431 0.3168 0.9760 0.050 Uiso 1 1 calc R . .
C20 C 0.2529(14) 0.3450(4) 0.9709(5) 0.041(2) Uani 1 1 d U . .
C21 C 0.5201(11) 0.2850(6) 0.7518(6) 0.050(2) Uani 1 1 d U . .
H21A H 0.5572 0.3192 0.7953 0.060 Uiso 1 1 calc R . .
H21B H 0.6003 0.2524 0.7314 0.060 Uiso 1 1 calc R . .
C22 C 0.4664(12) 0.3377(6) 0.6858(7) 0.046(3) Uani 1 1 d U . .
C23 C 0.4865(13) 0.3171(6) 0.6083(7) 0.050(3) Uani 1 1 d U . .
C24 C 0.4437(15) 0.3617(6) 0.5433(7) 0.069(4) Uani 1 1 d U . .
H24 H 0.4637 0.3461 0.4900 0.082 Uiso 1 1 calc R . .
C25 C 0.3698(15) 0.4307(6) 0.5616(8) 0.071(4) Uani 1 1 d U . .
H25 H 0.3304 0.4622 0.5199 0.086 Uiso 1 1 calc R . .
C26 C 0.3527(14) 0.4540(6) 0.6384(8) 0.064(3) Uani 1 1 d U . .
H26 H 0.3073 0.5036 0.6496 0.077 Uiso 1 1 calc R . .
C27 C 0.3995(11) 0.4075(5) 0.6997(7) 0.053(3) Uani 1 1 d U . .
H27 H 0.3847 0.4247 0.7531 0.063 Uiso 1 1 calc R . .
C28 C 0.1517(14) 0.6374(5) 0.8209(7) 0.069(3) Uani 1 1 d U . .
H28A H 0.0595 0.6303 0.8487 0.083 Uiso 1 1 calc R . .
H28B H 0.1906 0.6903 0.8362 0.083 Uiso 1 1 calc R . .
Cl1 Cl 0.2704(6) 0.56204(19) 0.8516(2) 0.1128(16) Uani 1 1 d U . .
Cl2 Cl 0.1231(4) 0.63554(17) 0.7183(2) 0.0852(11) Uani 1 1 d 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 N3 1.822(8) . ?
Ni1 N2 1.827(8) . ?
Ni1 O2 1.837(7) . ?
Ni1 N1 1.903(8) . ?
F1 C23 1.387(11) . ?
O1 C5 1.220(10) . ?
O2 C20 1.316(11) . ?
O3 C20 1.199(10) . ?
N1 C1 1.469(11) . ?
N1 C4 1.487(11) . ?
N1 C21 1.501(12) . ?
N2 C5 1.376(10) . ?
N2 C6 1.403(12) . ?
N3 C12 1.297(12) . ?
N3 C19 1.480(12) . ?
C1 C2 1.523(14) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.493(13) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.591(12) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.488(13) . ?
C4 H4 1.0000 . ?
C6 C11 1.379(12) . ?
C6 C7 1.440(13) . ?
C7 C8 1.342(14) . ?
C7 H7 0.9500 . ?
C8 C9 1.357(13) . ?
C8 H8 0.9500 . ?
C9 C10 1.376(13) . ?
C9 H9 0.9500 . ?
C10 C11 1.419(14) . ?
C10 H10 0.9500 . ?
C11 C12 1.455(13) . ?
C12 C13 1.443(13) . ?
C13 C18 1.392(13) . ?
C13 C14 1.405(11) . ?
C14 C15 1.346(14) . ?
C14 H14 0.9500 . ?
C15 C16 1.394(13) . ?
C15 H15 0.9500 . ?
C16 C17 1.372(12) . ?
C16 H16 0.9500 . ?
C17 C18 1.345(14) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.469(15) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C21 C22 1.499(13) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C27 1.345(13) . ?
C22 C23 1.358(15) . ?
C23 C24 1.379(14) . ?
C24 C25 1.379(15) . ?
C24 H24 0.9500 . ?
C25 C26 1.354(16) . ?
C25 H25 0.9500 . ?
C26 C27 1.360(14) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 Cl2 1.740(12) . ?
C28 Cl1 1.758(12) . ?
C28 H28A 0.9900 . ?
C28 H28B 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
N3 Ni1 N2 94.5(4) . . ?
N3 Ni1 O2 87.5(3) . . ?
N2 Ni1 O2 177.8(3) . . ?
N3 Ni1 N1 176.9(3) . . ?
N2 Ni1 N1 86.9(3) . . ?
O2 Ni1 N1 91.1(3) . . ?
C20 O2 Ni1 116.4(7) . . ?
C1 N1 C4 104.3(6) . . ?
C1 N1 C21 108.1(8) . . ?
C4 N1 C21 112.8(8) . . ?
C1 N1 Ni1 113.9(6) . . ?
C4 N1 Ni1 105.8(6) . . ?
C21 N1 Ni1 111.8(5) . . ?
C5 N2 C6 120.6(8) . . ?
C5 N2 Ni1 115.0(6) . . ?
C6 N2 Ni1 124.3(6) . . ?
C12 N3 C19 119.5(9) . . ?
C12 N3 Ni1 130.1(7) . . ?
C19 N3 Ni1 110.3(7) . . ?
N1 C1 C2 102.0(8) . . ?
N1 C1 H1A 111.4 . . ?
C2 C1 H1A 111.4 . . ?
N1 C1 H1B 111.4 . . ?
C2 C1 H1B 111.4 . . ?
H1A C1 H1B 109.2 . . ?
C3 C2 C1 104.7(8) . . ?
C3 C2 H2A 110.8 . . ?
C1 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
C1 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
C2 C3 C4 102.9(7) . . ?
C2 C3 H3A 111.2 . . ?
C4 C3 H3A 111.2 . . ?
C2 C3 H3B 111.2 . . ?
C4 C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
N1 C4 C5 112.0(7) . . ?
N1 C4 C3 105.7(7) . . ?
C5 C4 C3 111.1(8) . . ?
N1 C4 H4 109.3 . . ?
C5 C4 H4 109.3 . . ?
C3 C4 H4 109.3 . . ?
O1 C5 N2 127.1(10) . . ?
O1 C5 C4 121.4(9) . . ?
N2 C5 C4 111.4(9) . . ?
C11 C6 N2 122.1(9) . . ?
C11 C6 C7 118.9(10) . . ?
N2 C6 C7 118.9(8) . . ?
C8 C7 C6 117.7(10) . . ?
C8 C7 H7 121.1 . . ?
C6 C7 H7 121.1 . . ?
C7 C8 C9 125.0(10) . . ?
C7 C8 H8 117.5 . . ?
C9 C8 H8 117.5 . . ?
C8 C9 C10 118.4(10) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
C9 C10 C11 120.0(10) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C6 C11 C10 119.9(9) . . ?
C6 C11 C12 123.3(10) . . ?
C10 C11 C12 116.7(9) . . ?
N3 C12 C13 119.0(9) . . ?
N3 C12 C11 121.0(9) . . ?
C13 C12 C11 119.9(9) . . ?
C18 C13 C14 115.6(9) . . ?
C18 C13 C12 121.0(8) . . ?
C14 C13 C12 123.4(9) . . ?
C15 C14 C13 123.5(10) . . ?
C15 C14 H14 118.2 . . ?
C13 C14 H14 118.2 . . ?
C14 C15 C16 119.2(9) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C17 C16 C15 118.0(10) . . ?
C17 C16 H16 121.0 . . ?
C15 C16 H16 121.0 . . ?
C18 C17 C16 122.6(9) . . ?
C18 C17 H17 118.7 . . ?
C16 C17 H17 118.7 . . ?
C17 C18 C13 121.0(8) . . ?
C17 C18 H18 119.5 . . ?
C13 C18 H18 119.5 . . ?
C20 C19 N3 111.2(9) . . ?
C20 C19 H19A 109.4 . . ?
N3 C19 H19A 109.4 . . ?
C20 C19 H19B 109.4 . . ?
N3 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
O3 C20 O2 125.2(12) . . ?
O3 C20 C19 122.1(10) . . ?
O2 C20 C19 112.5(9) . . ?
C22 C21 N1 113.3(8) . . ?
C22 C21 H21A 108.9 . . ?
N1 C21 H21A 108.9 . . ?
C22 C21 H21B 108.9 . . ?
N1 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
C27 C22 C23 116.7(10) . . ?
C27 C22 C21 122.6(11) . . ?
C23 C22 C21 120.7(9) . . ?
C22 C23 C24 125.4(11) . . ?
C22 C23 F1 119.6(10) . . ?
C24 C23 F1 114.9(10) . . ?
C25 C24 C23 114.9(11) . . ?
C25 C24 H24 122.5 . . ?
C23 C24 H24 122.5 . . ?
C26 C25 C24 120.8(11) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C25 C26 C27 121.0(11) . . ?
C25 C26 H26 119.5 . . ?
C27 C26 H26 119.5 . . ?
C22 C27 C26 121.0(11) . . ?
C22 C27 H27 119.5 . . ?
C26 C27 H27 119.5 . . ?
Cl2 C28 Cl1 111.9(6) . . ?
Cl2 C28 H28A 109.2 . . ?
Cl1 C28 H28A 109.2 . . ?
Cl2 C28 H28B 109.2 . . ?
Cl1 C28 H28B 109.2 . . ?
H28A C28 H28B 107.9 . . ?

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 Ni1 O2 C20 3.2(6) . . . . ?
N1 Ni1 O2 C20 -174.1(6) . . . . ?
N2 Ni1 N1 C1 -141.0(6) . . . . ?
O2 Ni1 N1 C1 39.8(6) . . . . ?
N2 Ni1 N1 C4 -27.0(5) . . . . ?
O2 Ni1 N1 C4 153.8(5) . . . . ?
N2 Ni1 N1 C21 96.1(6) . . . . ?
O2 Ni1 N1 C21 -83.1(6) . . . . ?
N3 Ni1 N2 C5 -155.3(6) . . . . ?
N1 Ni1 N2 C5 22.0(6) . . . . ?
N3 Ni1 N2 C6 21.3(7) . . . . ?
N1 Ni1 N2 C6 -161.4(7) . . . . ?
N2 Ni1 N3 C12 -5.6(8) . . . . ?
O2 Ni1 N3 C12 173.7(8) . . . . ?
N2 Ni1 N3 C19 170.3(6) . . . . ?
O2 Ni1 N3 C19 -10.4(6) . . . . ?
C4 N1 C1 C2 -43.4(10) . . . . ?
C21 N1 C1 C2 -163.6(8) . . . . ?
Ni1 N1 C1 C2 71.5(8) . . . . ?
N1 C1 C2 C3 43.7(10) . . . . ?
C1 C2 C3 C4 -25.9(10) . . . . ?
C1 N1 C4 C5 148.3(9) . . . . ?
C21 N1 C4 C5 -94.6(10) . . . . ?
Ni1 N1 C4 C5 27.9(9) . . . . ?
C1 N1 C4 C3 27.2(10) . . . . ?
C21 N1 C4 C3 144.3(8) . . . . ?
Ni1 N1 C4 C3 -93.2(7) . . . . ?
C2 C3 C4 N1 -0.2(11) . . . . ?
C2 C3 C4 C5 -121.9(9) . . . . ?
C6 N2 C5 O1 -8.6(14) . . . . ?
Ni1 N2 C5 O1 168.1(8) . . . . ?
C6 N2 C5 C4 173.5(8) . . . . ?
Ni1 N2 C5 C4 -9.8(10) . . . . ?
N1 C4 C5 O1 169.0(9) . . . . ?
C3 C4 C5 O1 -73.1(12) . . . . ?
N1 C4 C5 N2 -13.0(11) . . . . ?
C3 C4 C5 N2 104.9(9) . . . . ?
C5 N2 C6 C11 152.4(9) . . . . ?
Ni1 N2 C6 C11 -24.0(11) . . . . ?
C5 N2 C6 C7 -30.8(12) . . . . ?
Ni1 N2 C6 C7 152.8(7) . . . . ?
C11 C6 C7 C8 -3.0(14) . . . . ?
N2 C6 C7 C8 -179.9(8) . . . . ?
C6 C7 C8 C9 0.4(16) . . . . ?
C7 C8 C9 C10 0.9(16) . . . . ?
C8 C9 C10 C11 0.3(15) . . . . ?
N2 C6 C11 C10 -178.9(8) . . . . ?
C7 C6 C11 C10 4.2(13) . . . . ?
N2 C6 C11 C12 5.7(13) . . . . ?
C7 C6 C11 C12 -171.1(9) . . . . ?
C9 C10 C11 C6 -2.9(14) . . . . ?
C9 C10 C11 C12 172.7(8) . . . . ?
C19 N3 C12 C13 -5.1(12) . . . . ?
Ni1 N3 C12 C13 170.5(6) . . . . ?
C19 N3 C12 C11 175.8(7) . . . . ?
Ni1 N3 C12 C11 -8.7(12) . . . . ?
C6 C11 C12 N3 11.0(13) . . . . ?
C10 C11 C12 N3 -164.5(8) . . . . ?
C6 C11 C12 C13 -168.1(8) . . . . ?
C10 C11 C12 C13 16.4(12) . . . . ?
N3 C12 C13 C18 -82.2(12) . . . . ?
C11 C12 C13 C18 96.9(11) . . . . ?
N3 C12 C13 C14 95.8(11) . . . . ?
C11 C12 C13 C14 -85.0(12) . . . . ?
C18 C13 C14 C15 -0.9(16) . . . . ?
C12 C13 C14 C15 -179.0(11) . . . . ?
C13 C14 C15 C16 0.8(18) . . . . ?
C14 C15 C16 C17 -0.5(17) . . . . ?
C15 C16 C17 C18 0.4(17) . . . . ?
C16 C17 C18 C13 -0.5(18) . . . . ?
C14 C13 C18 C17 0.7(15) . . . . ?
C12 C13 C18 C17 178.9(10) . . . . ?
C12 N3 C19 C20 -168.2(7) . . . . ?
Ni1 N3 C19 C20 15.4(8) . . . . ?
Ni1 O2 C20 O3 -179.7(7) . . . . ?
Ni1 O2 C20 C19 5.3(9) . . . . ?
N3 C19 C20 O3 171.4(7) . . . . ?
N3 C19 C20 O2 -13.4(10) . . . . ?
C1 N1 C21 C22 178.1(8) . . . . ?
C4 N1 C21 C22 63.3(10) . . . . ?
Ni1 N1 C21 C22 -55.7(10) . . . . ?
N1 C21 C22 C27 84.5(13) . . . . ?
N1 C21 C22 C23 -97.0(12) . . . . ?
C27 C22 C23 C24 -0.2(19) . . . . ?
C21 C22 C23 C24 -178.8(11) . . . . ?
C27 C22 C23 F1 176.2(9) . . . . ?
C21 C22 C23 F1 -2.4(17) . . . . ?
C22 C23 C24 C25 -3(2) . . . . ?
F1 C23 C24 C25 -179.4(11) . . . . ?
C23 C24 C25 C26 5(2) . . . . ?
C24 C25 C26 C27 -4(2) . . . . ?
C23 C22 C27 C26 1.1(16) . . . . ?
C21 C22 C27 C26 179.7(11) . . . . ?
C25 C26 C27 C22 1.2(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.559
_refine_diff_density_min         -1.457
_refine_diff_density_rms         0.115

_database_code_depnum_ccdc_archive 'CCDC 1020153'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_14066
_vrf_CHEMW03_I                   
;
PROBLEM: ALERT: The ratio of given/expected molecular weight as
RESPONSE: ...Due to SQUEEZE option in PLATON.
;
_vrf_PLAT051_I                   
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      34.86 %     
RESPONSE: ...Due to SQUEEZE option in PLATON.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H26 F N3 Ni O3,2C H2 Cl2'
_chemical_formula_sum            'C30 H30 Cl4 F N3 Ni O3'
_chemical_formula_weight         700.08

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'
F F 0.0171 0.0103 '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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_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                   9.1183(19)
_cell_length_b                   14.255(3)
_cell_length_c                   23.374(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3038.2(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    585
_cell_measurement_theta_min      2.254
_cell_measurement_theta_max      23.275

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1440
_exptl_absorpt_coefficient_mu    1.034
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.692
_exptl_absorpt_correction_T_max  0.892
_exptl_absorpt_process_details   
;
absorption correction based on 3643 reflections(SADABS);Rint 0.0977 before
correction and 0.0595 after.
;


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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 Apex 2000 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            23982
_diffrn_reflns_av_R_equivalents  0.1504
_diffrn_reflns_av_sigmaI/netI    0.1948
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         26.00
_reflns_number_total             5973
_reflns_number_gt                3142
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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 F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0584P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(3)
_chemical_absolute_configuration ,syn
_refine_ls_number_reflns         5973
_refine_ls_number_parameters     326
_refine_ls_number_restraints     336
_refine_ls_R_factor_all          0.1159
_refine_ls_R_factor_gt           0.0716
_refine_ls_wR_factor_ref         0.1645
_refine_ls_wR_factor_gt          0.1515
_refine_ls_goodness_of_fit_ref   0.869
_refine_ls_restrained_S_all      0.854
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.003 0.250 0.500 408 191 ' '
2 -0.053 0.750 1.000 408 191 ' '
_platon_squeeze_details          
;

Disordered CH2Cl2 was omitted using the SQUEEZE option of PLATON.The
solvent accessible voids are 813.0 3 with an estimated 382e/cell to 
be added.Eight solvent CH2Cl2 molecules/unit cell accounting for 336e
were included in the formula, FWt, (000) and density calculations. 
PLATON Reference: Spek, A.L. (1990), Acta Cryst. A46, C-34.

;



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 0.68864(10) 0.89879(6) 0.33219(4) 0.0310(2) Uani 1 1 d U . .
F1 F 0.9212(5) 0.9668(3) 0.2590(2) 0.0622(14) Uani 1 1 d U . .
O1 O 0.6405(5) 0.8076(3) 0.2782(2) 0.0424(13) Uani 1 1 d U . .
O2 O 0.6562(5) 0.6550(3) 0.2617(2) 0.0425(13) Uani 1 1 d U . .
O3 O 0.6479(7) 1.1342(4) 0.4148(2) 0.0656(19) Uani 1 1 d U . .
N1 N 0.7993(7) 0.8090(3) 0.3688(2) 0.0338(13) Uani 1 1 d U . .
N2 N 0.7435(6) 0.9955(4) 0.3801(2) 0.0384(14) Uani 1 1 d U . .
N3 N 0.5574(6) 0.9858(4) 0.2949(2) 0.0313(13) Uani 1 1 d U . .
C1 C 0.6827(9) 0.7210(5) 0.2914(3) 0.0377(17) Uani 1 1 d U . .
C2 C 0.7563(8) 0.7138(4) 0.3478(3) 0.0322(16) Uani 1 1 d U . .
H2 H 0.8441 0.6720 0.3453 0.039 Uiso 1 1 calc R . .
C3 C 0.9055(8) 0.8232(5) 0.4054(3) 0.0322(16) Uani 1 1 d U . .
C4 C 0.9928(8) 0.7364(5) 0.4257(3) 0.0401(19) Uani 1 1 d U . .
C5 C 0.9632(9) 0.6950(6) 0.4807(3) 0.052(2) Uani 1 1 d U . .
H5 H 0.8833 0.7179 0.5028 0.063 Uiso 1 1 calc R . .
C6 C 1.0432(10) 0.6270(6) 0.5010(4) 0.062(2) Uani 1 1 d U . .
H6 H 1.0275 0.6059 0.5391 0.074 Uiso 1 1 calc R . .
C7 C 1.1542(12) 0.5838(6) 0.4669(4) 0.075(3) Uani 1 1 d U . .
H7 H 1.2089 0.5313 0.4800 0.091 Uiso 1 1 calc R . .
C8 C 1.1769(11) 0.6226(5) 0.4138(3) 0.059(2) Uani 1 1 d U . .
H8 H 1.2506 0.5960 0.3900 0.071 Uiso 1 1 calc R . .
C9 C 1.1030(9) 0.6937(7) 0.3944(3) 0.058(2) Uani 1 1 d U . .
H9 H 1.1255 0.7172 0.3574 0.069 Uiso 1 1 calc R . .
C10 C 0.9535(7) 0.9091(5) 0.4244(3) 0.0363(16) Uani 1 1 d U . .
C11 C 1.0787(8) 0.9179(5) 0.4576(3) 0.0425(18) Uani 1 1 d U . .
H11 H 1.1308 0.8621 0.4667 0.051 Uiso 1 1 calc R . .
C12 C 1.1326(9) 1.0002(5) 0.4783(3) 0.049(2) Uani 1 1 d U . .
H12 H 1.2214 1.0017 0.4996 0.059 Uiso 1 1 calc R . .
C13 C 1.0538(8) 1.0828(6) 0.4673(3) 0.047(2) Uani 1 1 d U . .
H13 H 1.0879 1.1410 0.4819 0.056 Uiso 1 1 calc R . .
C14 C 0.9284(8) 1.0797(4) 0.4356(3) 0.0427(19) Uani 1 1 d U . .
H14 H 0.8776 1.1368 0.4288 0.051 Uiso 1 1 calc R . .
C15 C 0.8712(8) 0.9981(5) 0.4129(3) 0.0348(17) Uani 1 1 d U . .
C16 C 0.6450(9) 1.0724(5) 0.3832(3) 0.0398(18) Uani 1 1 d U . .
C17 C 0.5218(7) 1.0624(5) 0.3388(3) 0.0368(16) Uani 1 1 d U . .
H17 H 0.5055 1.1237 0.3190 0.044 Uiso 1 1 calc R . .
C18 C 0.3736(7) 1.0274(6) 0.3671(3) 0.045(2) Uani 1 1 d U . .
H18A H 0.3855 1.0198 0.4089 0.054 Uiso 1 1 calc R . .
H18B H 0.2934 1.0726 0.3598 0.054 Uiso 1 1 calc R . .
C19 C 0.3420(7) 0.9380(5) 0.3404(3) 0.0450(19) Uani 1 1 d U . .
H19A H 0.2348 0.9281 0.3373 0.054 Uiso 1 1 calc R . .
H19B H 0.3850 0.8859 0.3628 0.054 Uiso 1 1 calc R . .
C20 C 0.4150(7) 0.9436(5) 0.2783(3) 0.0353(17) Uani 1 1 d U . .
H20A H 0.4271 0.8809 0.2608 0.042 Uiso 1 1 calc R . .
H20B H 0.3588 0.9847 0.2521 0.042 Uiso 1 1 calc R . .
C21 C 0.6276(7) 1.0273(4) 0.2420(3) 0.0308(16) Uani 1 1 d U . .
H21A H 0.6608 0.9752 0.2171 0.037 Uiso 1 1 calc R . .
H21B H 0.5520 1.0628 0.2207 0.037 Uiso 1 1 calc R . .
C22 C 0.7541(7) 1.0903(5) 0.2528(2) 0.0313(15) Uani 1 1 d U . .
C23 C 0.8971(9) 1.0605(5) 0.2623(3) 0.0418(18) Uani 1 1 d U . .
C24 C 1.0104(9) 1.1227(6) 0.2741(4) 0.052(2) Uani 1 1 d U . .
H24 H 1.1050 1.0993 0.2834 0.062 Uiso 1 1 calc R . .
C25 C 0.9887(9) 1.2102(6) 0.2725(3) 0.048(2) Uani 1 1 d U . .
H25 H 1.0705 1.2508 0.2770 0.057 Uiso 1 1 calc R . .
C26 C 0.8456(8) 1.2515(6) 0.2642(3) 0.0469(19) Uani 1 1 d U . .
H26 H 0.8313 1.3175 0.2645 0.056 Uiso 1 1 calc R . .
C27 C 0.7317(8) 1.1903(5) 0.2557(3) 0.0384(18) Uani 1 1 d U . .
H27 H 0.6352 1.2145 0.2518 0.046 Uiso 1 1 calc R . .
C28 C 0.6352(10) 0.6703(5) 0.3931(3) 0.057(3) Uani 1 1 d U . .
H28A H 0.6827 0.6585 0.4300 0.086 Uiso 1 1 calc R . .
H28B H 0.5959 0.6114 0.3778 0.086 Uiso 1 1 calc R . .
H28C H 0.5550 0.7153 0.3983 0.086 Uiso 1 1 calc R . .


_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 1.841(5) . ?
Ni1 N2 1.846(6) . ?
Ni1 O1 1.865(5) . ?
Ni1 N3 1.931(5) . ?
F1 C23 1.355(8) . ?
O1 C1 1.329(7) . ?
O2 C1 1.194(7) . ?
O3 C16 1.151(7) . ?
N1 C3 1.308(8) . ?
N1 C2 1.495(8) . ?
N2 C15 1.394(8) . ?
N2 C16 1.418(9) . ?
N3 C20 1.483(8) . ?
N3 C21 1.512(8) . ?
N3 C17 1.534(8) . ?
C1 C2 1.483(9) . ?
C2 C28 1.650(10) . ?
C2 H2 1.0000 . ?
C3 C10 1.375(9) . ?
C3 C4 1.545(9) . ?
C4 C9 1.384(10) . ?
C4 C5 1.442(9) . ?
C5 C6 1.302(10) . ?
C5 H5 0.9500 . ?
C6 C7 1.430(12) . ?
C6 H6 0.9500 . ?
C7 C8 1.374(11) . ?
C7 H7 0.9500 . ?
C8 C9 1.298(10) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.386(9) . ?
C10 C15 1.498(9) . ?
C11 C12 1.360(9) . ?
C11 H11 0.9500 . ?
C12 C13 1.404(10) . ?
C12 H12 0.9500 . ?
C13 C14 1.363(9) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(9) . ?
C14 H14 0.9500 . ?
C16 C17 1.535(9) . ?
C17 C18 1.584(9) . ?
C17 H17 1.0000 . ?
C18 C19 1.447(9) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.598(9) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.484(9) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.390(9) . ?
C22 C27 1.441(9) . ?
C23 C24 1.389(10) . ?
C24 C25 1.263(11) . ?
C24 H24 0.9500 . ?
C25 C26 1.445(10) . ?
C25 H25 0.9500 . ?
C26 C27 1.371(9) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 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
N1 Ni1 N2 95.1(2) . . ?
N1 Ni1 O1 87.6(2) . . ?
N2 Ni1 O1 174.7(2) . . ?
N1 Ni1 N3 174.8(3) . . ?
N2 Ni1 N3 87.8(2) . . ?
O1 Ni1 N3 89.8(2) . . ?
C1 O1 Ni1 115.0(4) . . ?
C3 N1 C2 123.3(5) . . ?
C3 N1 Ni1 127.0(4) . . ?
C2 N1 Ni1 109.6(4) . . ?
C15 N2 C16 118.7(6) . . ?
C15 N2 Ni1 125.4(5) . . ?
C16 N2 Ni1 115.9(5) . . ?
C20 N3 C21 108.4(5) . . ?
C20 N3 C17 106.2(5) . . ?
C21 N3 C17 111.0(5) . . ?
C20 N3 Ni1 113.6(4) . . ?
C21 N3 Ni1 111.0(4) . . ?
C17 N3 Ni1 106.6(4) . . ?
O2 C1 O1 122.5(6) . . ?
O2 C1 C2 123.6(6) . . ?
O1 C1 C2 113.7(6) . . ?
C1 C2 N1 110.3(5) . . ?
C1 C2 C28 107.1(6) . . ?
N1 C2 C28 107.8(5) . . ?
C1 C2 H2 110.5 . . ?
N1 C2 H2 110.5 . . ?
C28 C2 H2 110.5 . . ?
N1 C3 C10 125.8(6) . . ?
N1 C3 C4 117.3(6) . . ?
C10 C3 C4 116.7(6) . . ?
C9 C4 C5 115.3(7) . . ?
C9 C4 C3 124.4(7) . . ?
C5 C4 C3 120.3(7) . . ?
C6 C5 C4 121.7(8) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 120.9(8) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C8 C7 C6 116.0(8) . . ?
C8 C7 H7 122.0 . . ?
C6 C7 H7 122.0 . . ?
C9 C8 C7 123.4(9) . . ?
C9 C8 H8 118.3 . . ?
C7 C8 H8 118.3 . . ?
C8 C9 C4 122.5(8) . . ?
C8 C9 H9 118.8 . . ?
C4 C9 H9 118.8 . . ?
C3 C10 C11 121.6(7) . . ?
C3 C10 C15 122.4(6) . . ?
C11 C10 C15 115.9(7) . . ?
C12 C11 C10 125.1(8) . . ?
C12 C11 H11 117.5 . . ?
C10 C11 H11 117.5 . . ?
C11 C12 C13 118.2(7) . . ?
C11 C12 H12 120.9 . . ?
C13 C12 H12 120.9 . . ?
C14 C13 C12 120.2(7) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 123.5(7) . . ?
C13 C14 H14 118.2 . . ?
C15 C14 H14 118.2 . . ?
C14 C15 N2 123.3(7) . . ?
C14 C15 C10 117.1(6) . . ?
N2 C15 C10 119.7(6) . . ?
O3 C16 N2 127.6(7) . . ?
O3 C16 C17 121.4(7) . . ?
N2 C16 C17 111.0(6) . . ?
N3 C17 C16 111.3(5) . . ?
N3 C17 C18 103.6(5) . . ?
C16 C17 C18 111.8(6) . . ?
N3 C17 H17 110.0 . . ?
C16 C17 H17 110.0 . . ?
C18 C17 H17 110.0 . . ?
C19 C18 C17 105.5(6) . . ?
C19 C18 H18A 110.6 . . ?
C17 C18 H18A 110.6 . . ?
C19 C18 H18B 110.6 . . ?
C17 C18 H18B 110.6 . . ?
H18A C18 H18B 108.8 . . ?
C18 C19 C20 105.3(6) . . ?
C18 C19 H19A 110.7 . . ?
C20 C19 H19A 110.7 . . ?
C18 C19 H19B 110.7 . . ?
C20 C19 H19B 110.7 . . ?
H19A C19 H19B 108.8 . . ?
N3 C20 C19 98.4(5) . . ?
N3 C20 H20A 112.1 . . ?
C19 C20 H20A 112.1 . . ?
N3 C20 H20B 112.1 . . ?
C19 C20 H20B 112.1 . . ?
H20A C20 H20B 109.7 . . ?
C22 C21 N3 115.3(5) . . ?
C22 C21 H21A 108.4 . . ?
N3 C21 H21A 108.4 . . ?
C22 C21 H21B 108.4 . . ?
N3 C21 H21B 108.4 . . ?
H21A C21 H21B 107.5 . . ?
C23 C22 C27 115.3(6) . . ?
C23 C22 C21 124.8(6) . . ?
C27 C22 C21 119.8(6) . . ?
F1 C23 C24 121.3(7) . . ?
F1 C23 C22 116.4(7) . . ?
C24 C23 C22 122.3(7) . . ?
C25 C24 C23 120.5(8) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C24 C25 C26 123.2(8) . . ?
C24 C25 H25 118.4 . . ?
C26 C25 H25 118.4 . . ?
C27 C26 C25 116.4(7) . . ?
C27 C26 H26 121.8 . . ?
C25 C26 H26 121.8 . . ?
C26 C27 C22 122.0(7) . . ?
C26 C27 H27 119.0 . . ?
C22 C27 H27 119.0 . . ?
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 O1 C1 8.8(5) . . . . ?
N3 Ni1 O1 C1 -166.7(5) . . . . ?
N2 Ni1 N1 C3 -15.4(6) . . . . ?
O1 Ni1 N1 C3 160.1(6) . . . . ?
N2 Ni1 N1 C2 168.1(4) . . . . ?
O1 Ni1 N1 C2 -16.4(4) . . . . ?
N1 Ni1 N2 C15 23.2(6) . . . . ?
N3 Ni1 N2 C15 -161.1(6) . . . . ?
N1 Ni1 N2 C16 -156.5(5) . . . . ?
N3 Ni1 N2 C16 19.2(5) . . . . ?
N2 Ni1 N3 C20 -141.3(5) . . . . ?
O1 Ni1 N3 C20 43.5(5) . . . . ?
N2 Ni1 N3 C21 96.3(4) . . . . ?
O1 Ni1 N3 C21 -78.9(4) . . . . ?
N2 Ni1 N3 C17 -24.6(4) . . . . ?
O1 Ni1 N3 C17 160.1(4) . . . . ?
Ni1 O1 C1 O2 178.0(6) . . . . ?
Ni1 O1 C1 C2 1.8(8) . . . . ?
O2 C1 C2 N1 169.1(7) . . . . ?
O1 C1 C2 N1 -14.8(8) . . . . ?
O2 C1 C2 C28 -73.9(9) . . . . ?
O1 C1 C2 C28 102.2(7) . . . . ?
C3 N1 C2 C1 -155.8(6) . . . . ?
Ni1 N1 C2 C1 20.8(6) . . . . ?
C3 N1 C2 C28 87.6(8) . . . . ?
Ni1 N1 C2 C28 -95.7(5) . . . . ?
C2 N1 C3 C10 177.3(6) . . . . ?
Ni1 N1 C3 C10 1.2(11) . . . . ?
C2 N1 C3 C4 2.2(10) . . . . ?
Ni1 N1 C3 C4 -173.8(5) . . . . ?
N1 C3 C4 C9 79.4(10) . . . . ?
C10 C3 C4 C9 -96.0(9) . . . . ?
N1 C3 C4 C5 -101.3(8) . . . . ?
C10 C3 C4 C5 83.2(9) . . . . ?
C9 C4 C5 C6 5.2(12) . . . . ?
C3 C4 C5 C6 -174.1(8) . . . . ?
C4 C5 C6 C7 -6.8(13) . . . . ?
C5 C6 C7 C8 4.4(13) . . . . ?
C6 C7 C8 C9 -0.6(14) . . . . ?
C7 C8 C9 C4 -0.7(14) . . . . ?
C5 C4 C9 C8 -1.5(12) . . . . ?
C3 C4 C9 C8 177.8(8) . . . . ?
N1 C3 C10 C11 -171.7(7) . . . . ?
C4 C3 C10 C11 3.3(10) . . . . ?
N1 C3 C10 C15 11.0(11) . . . . ?
C4 C3 C10 C15 -173.9(6) . . . . ?
C3 C10 C11 C12 -179.7(7) . . . . ?
C15 C10 C11 C12 -2.2(11) . . . . ?
C10 C11 C12 C13 2.5(12) . . . . ?
C11 C12 C13 C14 -1.4(12) . . . . ?
C12 C13 C14 C15 0.2(12) . . . . ?
C13 C14 C15 N2 -179.4(7) . . . . ?
C13 C14 C15 C10 0.1(11) . . . . ?
C16 N2 C15 C14 -18.6(10) . . . . ?
Ni1 N2 C15 C14 161.7(6) . . . . ?
C16 N2 C15 C10 161.9(6) . . . . ?
Ni1 N2 C15 C10 -17.8(9) . . . . ?
C3 C10 C15 C14 178.3(7) . . . . ?
C11 C10 C15 C14 0.9(9) . . . . ?
C3 C10 C15 N2 -2.2(10) . . . . ?
C11 C10 C15 N2 -179.6(6) . . . . ?
C15 N2 C16 O3 -9.7(11) . . . . ?
Ni1 N2 C16 O3 170.0(7) . . . . ?
C15 N2 C16 C17 172.9(6) . . . . ?
Ni1 N2 C16 C17 -7.4(7) . . . . ?
C20 N3 C17 C16 147.4(5) . . . . ?
C21 N3 C17 C16 -95.0(6) . . . . ?
Ni1 N3 C17 C16 25.9(6) . . . . ?
C20 N3 C17 C18 27.1(6) . . . . ?
C21 N3 C17 C18 144.7(5) . . . . ?
Ni1 N3 C17 C18 -94.4(5) . . . . ?
O3 C16 C17 N3 169.4(7) . . . . ?
N2 C16 C17 N3 -13.0(8) . . . . ?
O3 C16 C17 C18 -75.4(9) . . . . ?
N2 C16 C17 C18 102.2(7) . . . . ?
N3 C17 C18 C19 2.0(7) . . . . ?
C16 C17 C18 C19 -117.9(7) . . . . ?
C17 C18 C19 C20 -28.1(8) . . . . ?
C21 N3 C20 C19 -161.7(5) . . . . ?
C17 N3 C20 C19 -42.4(6) . . . . ?
Ni1 N3 C20 C19 74.4(5) . . . . ?
C18 C19 C20 N3 44.3(7) . . . . ?
C20 N3 C21 C22 167.0(6) . . . . ?
C17 N3 C21 C22 50.8(7) . . . . ?
Ni1 N3 C21 C22 -67.6(6) . . . . ?
N3 C21 C22 C23 82.4(8) . . . . ?
N3 C21 C22 C27 -95.5(7) . . . . ?
C27 C22 C23 F1 -179.1(6) . . . . ?
C21 C22 C23 F1 2.9(10) . . . . ?
C27 C22 C23 C24 0.2(10) . . . . ?
C21 C22 C23 C24 -177.8(7) . . . . ?
F1 C23 C24 C25 174.2(7) . . . . ?
C22 C23 C24 C25 -5.1(13) . . . . ?
C23 C24 C25 C26 6.1(13) . . . . ?
C24 C25 C26 C27 -2.3(12) . . . . ?
C25 C26 C27 C22 -2.7(10) . . . . ?
C23 C22 C27 C26 3.6(10) . . . . ?
C21 C22 C27 C26 -178.3(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.085

_database_code_depnum_ccdc_archive 'CCDC 1020154'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_14079

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H32 F N3 Ni O3, C4 H8 O2'
_chemical_formula_sum            'C36 H40 F N3 Ni O5'
_chemical_formula_weight         672.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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)

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

_cell_length_a                   9.054(3)
_cell_length_b                   14.587(4)
_cell_length_c                   12.850(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.348(6)
_cell_angle_gamma                90.00
_cell_volume                     1664.0(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    683
_cell_measurement_theta_min      2.534
_cell_measurement_theta_max      23.159

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             708
_exptl_absorpt_coefficient_mu    0.635
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.406
_exptl_absorpt_correction_T_max  0.894
_exptl_absorpt_process_details   
;
absorption correction based on 3954 reflections(SADABS);Rint 0.1397 before
correction and 0.0661 after.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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 Apex 2000 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            13122
_diffrn_reflns_av_R_equivalents  0.0973
_diffrn_reflns_av_sigmaI/netI    0.1548
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.62
_diffrn_reflns_theta_max         25.99
_reflns_number_total             6380
_reflns_number_gt                4276
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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 F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0198P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.072(18)
_chemical_absolute_configuration ,syn
_refine_ls_number_reflns         6380
_refine_ls_number_parameters     417
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0602
_refine_ls_wR_factor_ref         0.1082
_refine_ls_wR_factor_gt          0.0964
_refine_ls_goodness_of_fit_ref   0.877
_refine_ls_restrained_S_all      0.877
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.78097(7) 0.95707(5) 0.35447(5) 0.02421(16) Uani 1 1 d . . .
F1 F 0.5895(4) 1.0076(2) 0.5228(3) 0.0571(11) Uani 1 1 d . . .
O1 O 0.8499(4) 0.8540(2) 0.4349(3) 0.0314(9) Uani 1 1 d . . .
O2 O 0.8226(4) 0.7031(2) 0.4398(3) 0.0300(9) Uani 1 1 d . . .
O3 O 0.8262(4) 1.1956(3) 0.2273(3) 0.0379(10) Uani 1 1 d . . .
N1 N 0.6363(5) 0.8822(3) 0.2768(3) 0.0226(10) Uani 1 1 d . . .
N2 N 0.7166(5) 1.0607(3) 0.2778(3) 0.0245(10) Uani 1 1 d . . .
N3 N 0.9359(5) 1.0325(3) 0.4377(3) 0.0244(10) Uani 1 1 d . . .
C1 C 0.7886(5) 0.7780(3) 0.3964(4) 0.0247(12) Uani 1 1 d . . .
C2 C 0.6814(6) 0.7845(3) 0.2927(4) 0.0242(12) Uani 1 1 d . . .
H2 H 0.5904 0.7464 0.2953 0.029 Uiso 1 1 calc R . .
C3 C 0.5101(6) 0.9063(4) 0.2137(4) 0.0252(14) Uani 1 1 d . . .
C4 C 0.3984(6) 0.8338(3) 0.1693(4) 0.0249(12) Uani 1 1 d . . .
C5 C 0.3744(6) 0.8088(4) 0.0637(4) 0.0312(13) Uani 1 1 d . . .
H5 H 0.4319 0.8364 0.0177 0.037 Uiso 1 1 calc R . .
C6 C 0.2657(6) 0.7431(4) 0.0246(5) 0.0392(15) Uani 1 1 d . . .
H6 H 0.2497 0.7258 -0.0480 0.047 Uiso 1 1 calc R . .
C7 C 0.1810(6) 0.7031(4) 0.0910(5) 0.0437(16) Uani 1 1 d . . .
H7 H 0.1051 0.6596 0.0638 0.052 Uiso 1 1 calc R . .
C8 C 0.2073(6) 0.7264(4) 0.1960(5) 0.0364(14) Uani 1 1 d . . .
H8 H 0.1514 0.6975 0.2420 0.044 Uiso 1 1 calc R . .
C9 C 0.3141(6) 0.7915(3) 0.2360(4) 0.0270(12) Uani 1 1 d . . .
H9 H 0.3304 0.8076 0.3090 0.032 Uiso 1 1 calc R . .
C10 C 0.4720(6) 1.0014(4) 0.1892(4) 0.0259(14) Uani 1 1 d . . .
C11 C 0.3263(6) 1.0203(4) 0.1297(4) 0.0270(13) Uani 1 1 d . . .
H11 H 0.2586 0.9709 0.1088 0.032 Uiso 1 1 calc R . .
C12 C 0.2810(6) 1.1068(4) 0.1017(4) 0.0305(13) Uani 1 1 d . . .
H12 H 0.1829 1.1171 0.0609 0.037 Uiso 1 1 calc R . .
C13 C 0.3754(6) 1.1798(4) 0.1318(4) 0.0347(14) Uani 1 1 d . . .
H13 H 0.3425 1.2405 0.1128 0.042 Uiso 1 1 calc R . .
C14 C 0.5180(6) 1.1645(3) 0.1896(4) 0.0299(13) Uani 1 1 d . . .
H14 H 0.5824 1.2155 0.2106 0.036 Uiso 1 1 calc R . .
C15 C 0.5710(6) 1.0769(3) 0.2183(4) 0.0232(12) Uani 1 1 d . . .
C16 C 0.8287(6) 1.1260(3) 0.2820(4) 0.0264(13) Uani 1 1 d . . .
C17 C 0.9670(6) 1.1042(3) 0.3627(4) 0.0267(12) Uani 1 1 d . . .
H17 H 1.0056 1.1609 0.4027 0.032 Uiso 1 1 calc R . .
C18 C 1.0908(6) 1.0629(4) 0.3089(5) 0.0397(15) Uani 1 1 d . . .
H18A H 1.1766 1.1058 0.3141 0.048 Uiso 1 1 calc R . .
H18B H 1.0501 1.0501 0.2331 0.048 Uiso 1 1 calc R . .
C19 C 1.1417(6) 0.9726(5) 0.3698(4) 0.0446(17) Uani 1 1 d . . .
H19A H 1.0952 0.9183 0.3300 0.054 Uiso 1 1 calc R . .
H19B H 1.2527 0.9660 0.3839 0.054 Uiso 1 1 calc R . .
C20 C 1.0840(6) 0.9857(3) 0.4719(4) 0.0309(14) Uani 1 1 d . . .
H20A H 1.0714 0.9260 0.5057 0.037 Uiso 1 1 calc R . .
H20B H 1.1541 1.0242 0.5227 0.037 Uiso 1 1 calc R . .
C21 C 0.8868(6) 1.0700(4) 0.5336(4) 0.0292(13) Uani 1 1 d . . .
H21A H 0.9717 1.1046 0.5762 0.035 Uiso 1 1 calc R . .
H21B H 0.8642 1.0180 0.5775 0.035 Uiso 1 1 calc R . .
C22 C 0.7513(6) 1.1317(4) 0.5106(4) 0.0279(13) Uani 1 1 d . . .
C23 C 0.6067(7) 1.0990(4) 0.5054(5) 0.0389(15) Uani 1 1 d . . .
C24 C 0.4815(7) 1.1536(5) 0.4864(5) 0.0457(18) Uani 1 1 d . . .
H24 H 0.3843 1.1287 0.4856 0.055 Uiso 1 1 calc R . .
C25 C 0.4999(7) 1.2458(5) 0.4685(5) 0.0453(18) Uani 1 1 d . . .
H25 H 0.4143 1.2847 0.4537 0.054 Uiso 1 1 calc R . .
C26 C 0.6390(7) 1.2812(4) 0.4716(4) 0.0376(15) Uani 1 1 d . . .
H26 H 0.6501 1.3445 0.4578 0.045 Uiso 1 1 calc R . .
C27 C 0.7652(6) 1.2257(4) 0.4947(4) 0.0325(14) Uani 1 1 d . . .
H27 H 0.8624 1.2519 0.4998 0.039 Uiso 1 1 calc R . .
C28 C 0.7542(6) 0.7515(4) 0.1996(4) 0.0290(13) Uani 1 1 d . . .
H28A H 0.6882 0.7696 0.1318 0.035 Uiso 1 1 calc R . .
H28B H 0.8518 0.7833 0.2039 0.035 Uiso 1 1 calc R . .
C29 C 0.7808(6) 0.6490(4) 0.1981(5) 0.0353(14) Uani 1 1 d . . .
H29A H 0.8438 0.6355 0.1451 0.042 Uiso 1 1 calc R . .
H29B H 0.8385 0.6301 0.2685 0.042 Uiso 1 1 calc R . .
C30 C 0.6398(7) 0.5920(4) 0.1725(5) 0.0443(16) Uani 1 1 d . . .
H30A H 0.5775 0.6033 0.2265 0.053 Uiso 1 1 calc R . .
H30B H 0.5805 0.6108 0.1026 0.053 Uiso 1 1 calc R . .
C31 C 0.6752(8) 0.4915(4) 0.1700(6) 0.060(2) Uani 1 1 d . . .
H31 H 0.7329 0.4719 0.1199 0.072 Uiso 1 1 calc R . .
C32 C 0.6341(12) 0.4294(5) 0.2301(7) 0.109(4) Uani 1 1 d . . .
H32A H 0.5762 0.4460 0.2813 0.131 Uiso 1 1 calc R . .
H32B H 0.6617 0.3672 0.2230 0.131 Uiso 1 1 calc R . .
O4 O 0.0094(6) 0.4887(3) 0.0283(5) 0.0855(19) Uani 1 1 d . . .
O5 O 0.1659(6) 0.3836(4) 0.1032(5) 0.113(3) Uani 1 1 d . . .
C33 C 0.1271(7) 0.4479(5) 0.0355(5) 0.0514(16) Uani 1 1 d . . .
C34 C 0.2485(8) 0.4755(5) -0.0202(5) 0.068(2) Uani 1 1 d . . .
H34A H 0.2043 0.5059 -0.0871 0.102 Uiso 1 1 calc R . .
H34B H 0.3042 0.4210 -0.0350 0.102 Uiso 1 1 calc R . .
H34C H 0.3173 0.5179 0.0246 0.102 Uiso 1 1 calc R . .
C35 C 0.0626(10) 0.3593(10) 0.1703(9) 0.193(8) Uani 1 1 d . . .
H35A H -0.0190 0.4056 0.1610 0.232 Uiso 1 1 calc R . .
H35B H 0.0162 0.2995 0.1466 0.232 Uiso 1 1 calc R . .
C36 C 0.1253(12) 0.3534(7) 0.2757(7) 0.118(4) Uani 1 1 d . . .
H36A H 0.2046 0.3066 0.2864 0.176 Uiso 1 1 calc R . .
H36B H 0.0475 0.3364 0.3156 0.176 Uiso 1 1 calc R . .
H36C H 0.1687 0.4128 0.3009 0.176 Uiso 1 1 calc R . .


_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 1.835(4) . ?
Ni1 N1 1.842(4) . ?
Ni1 O1 1.862(4) . ?
Ni1 N3 1.932(4) . ?
F1 C23 1.365(6) . ?
O1 C1 1.293(6) . ?
O2 C1 1.238(6) . ?
O3 C16 1.232(6) . ?
N1 C3 1.312(7) . ?
N1 C2 1.485(6) . ?
N2 C16 1.386(6) . ?
N2 C15 1.408(6) . ?
N3 C17 1.486(6) . ?
N3 C20 1.492(6) . ?
N3 C21 1.493(6) . ?
C1 C2 1.490(7) . ?
C2 C28 1.552(7) . ?
C2 H2 1.0000 . ?
C3 C10 1.448(6) . ?
C3 C4 1.497(7) . ?
C4 C5 1.380(7) . ?
C4 C9 1.397(7) . ?
C5 C6 1.395(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.384(8) . ?
C6 H6 0.9500 . ?
C7 C8 1.365(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.380(7) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.415(7) . ?
C10 C15 1.423(7) . ?
C11 C12 1.354(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.373(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.375(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(6) . ?
C14 H14 0.9500 . ?
C16 C17 1.495(7) . ?
C17 C18 1.549(7) . ?
C17 H17 1.0000 . ?
C18 C19 1.555(8) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.517(7) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.503(7) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.383(7) . ?
C22 C27 1.395(7) . ?
C23 C24 1.368(8) . ?
C24 C25 1.379(7) . ?
C24 H24 0.9500 . ?
C25 C26 1.355(8) . ?
C25 H25 0.9500 . ?
C26 C27 1.384(7) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C29 1.516(7) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.505(7) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.503(7) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.291(9) . ?
C31 H31 0.9500 . ?
C32 H32A 0.9500 . ?
C32 H32B 0.9500 . ?
O4 C33 1.207(7) . ?
O5 C33 1.281(8) . ?
O5 C35 1.436(9) . ?
C33 C34 1.481(8) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 C36 1.364(12) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 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
N2 Ni1 N1 94.63(19) . . ?
N2 Ni1 O1 178.4(2) . . ?
N1 Ni1 O1 86.94(17) . . ?
N2 Ni1 N3 86.98(19) . . ?
N1 Ni1 N3 178.3(2) . . ?
O1 Ni1 N3 91.45(18) . . ?
C1 O1 Ni1 114.1(3) . . ?
C3 N1 C2 121.7(4) . . ?
C3 N1 Ni1 128.0(4) . . ?
C2 N1 Ni1 110.3(3) . . ?
C16 N2 C15 120.4(4) . . ?
C16 N2 Ni1 113.1(3) . . ?
C15 N2 Ni1 126.5(3) . . ?
C17 N3 C20 103.8(4) . . ?
C17 N3 C21 113.7(4) . . ?
C20 N3 C21 108.7(4) . . ?
C17 N3 Ni1 104.6(3) . . ?
C20 N3 Ni1 114.5(3) . . ?
C21 N3 Ni1 111.4(3) . . ?
O2 C1 O1 122.3(5) . . ?
O2 C1 C2 121.3(4) . . ?
O1 C1 C2 116.3(5) . . ?
N1 C2 C1 107.3(4) . . ?
N1 C2 C28 109.8(4) . . ?
C1 C2 C28 111.7(4) . . ?
N1 C2 H2 109.3 . . ?
C1 C2 H2 109.3 . . ?
C28 C2 H2 109.3 . . ?
N1 C3 C10 122.2(5) . . ?
N1 C3 C4 119.1(5) . . ?
C10 C3 C4 118.6(5) . . ?
C5 C4 C9 119.1(5) . . ?
C5 C4 C3 121.6(5) . . ?
C9 C4 C3 119.2(5) . . ?
C4 C5 C6 119.9(5) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C7 C6 C5 120.3(5) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C8 C7 C6 119.6(5) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C7 C8 C9 120.9(5) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C8 C9 C4 120.1(5) . . ?
C8 C9 H9 119.9 . . ?
C4 C9 H9 119.9 . . ?
C11 C10 C15 117.6(5) . . ?
C11 C10 C3 117.4(5) . . ?
C15 C10 C3 125.0(5) . . ?
C12 C11 C10 121.8(5) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 120.6(5) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C14 119.5(5) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 122.1(5) . . ?
C13 C14 H14 119.0 . . ?
C15 C14 H14 119.0 . . ?
C14 C15 N2 122.4(5) . . ?
C14 C15 C10 118.4(5) . . ?
N2 C15 C10 119.1(4) . . ?
O3 C16 N2 127.8(5) . . ?
O3 C16 C17 119.3(5) . . ?
N2 C16 C17 112.8(5) . . ?
N3 C17 C16 111.1(4) . . ?
N3 C17 C18 105.2(4) . . ?
C16 C17 C18 110.7(4) . . ?
N3 C17 H17 109.9 . . ?
C16 C17 H17 109.9 . . ?
C18 C17 H17 109.9 . . ?
C17 C18 C19 105.9(4) . . ?
C17 C18 H18A 110.6 . . ?
C19 C18 H18A 110.6 . . ?
C17 C18 H18B 110.6 . . ?
C19 C18 H18B 110.6 . . ?
H18A C18 H18B 108.7 . . ?
C20 C19 C18 102.1(4) . . ?
C20 C19 H19A 111.3 . . ?
C18 C19 H19A 111.3 . . ?
C20 C19 H19B 111.3 . . ?
C18 C19 H19B 111.3 . . ?
H19A C19 H19B 109.2 . . ?
N3 C20 C19 104.2(4) . . ?
N3 C20 H20A 110.9 . . ?
C19 C20 H20A 110.9 . . ?
N3 C20 H20B 110.9 . . ?
C19 C20 H20B 110.9 . . ?
H20A C20 H20B 108.9 . . ?
N3 C21 C22 114.9(4) . . ?
N3 C21 H21A 108.5 . . ?
C22 C21 H21A 108.5 . . ?
N3 C21 H21B 108.5 . . ?
C22 C21 H21B 108.5 . . ?
H21A C21 H21B 107.5 . . ?
C23 C22 C27 116.3(5) . . ?
C23 C22 C21 122.1(5) . . ?
C27 C22 C21 121.6(5) . . ?
F1 C23 C24 118.8(5) . . ?
F1 C23 C22 117.8(5) . . ?
C24 C23 C22 123.4(6) . . ?
C23 C24 C25 118.3(6) . . ?
C23 C24 H24 120.8 . . ?
C25 C24 H24 120.8 . . ?
C26 C25 C24 120.6(6) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C25 C26 C27 120.4(6) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C26 C27 C22 120.8(6) . . ?
C26 C27 H27 119.6 . . ?
C22 C27 H27 119.6 . . ?
C29 C28 C2 114.1(5) . . ?
C29 C28 H28A 108.7 . . ?
C2 C28 H28A 108.7 . . ?
C29 C28 H28B 108.7 . . ?
C2 C28 H28B 108.7 . . ?
H28A C28 H28B 107.6 . . ?
C30 C29 C28 114.7(5) . . ?
C30 C29 H29A 108.6 . . ?
C28 C29 H29A 108.6 . . ?
C30 C29 H29B 108.6 . . ?
C28 C29 H29B 108.6 . . ?
H29A C29 H29B 107.6 . . ?
C31 C30 C29 111.6(5) . . ?
C31 C30 H30A 109.3 . . ?
C29 C30 H30A 109.3 . . ?
C31 C30 H30B 109.3 . . ?
C29 C30 H30B 109.3 . . ?
H30A C30 H30B 108.0 . . ?
C32 C31 C30 125.7(7) . . ?
C32 C31 H31 117.2 . . ?
C30 C31 H31 117.2 . . ?
C31 C32 H32A 120.0 . . ?
C31 C32 H32B 120.0 . . ?
H32A C32 H32B 120.0 . . ?
C33 O5 C35 117.7(6) . . ?
O4 C33 O5 122.2(7) . . ?
O4 C33 C34 123.8(7) . . ?
O5 C33 C34 113.4(6) . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C36 C35 O5 114.8(9) . . ?
C36 C35 H35A 108.6 . . ?
O5 C35 H35A 108.6 . . ?
C36 C35 H35B 108.6 . . ?
O5 C35 H35B 108.6 . . ?
H35A C35 H35B 107.5 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 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 O1 C1 9.2(4) . . . . ?
N3 Ni1 O1 C1 -170.4(3) . . . . ?
N2 Ni1 N1 C3 -17.7(5) . . . . ?
O1 Ni1 N1 C3 162.1(5) . . . . ?
N2 Ni1 N1 C2 161.3(3) . . . . ?
O1 Ni1 N1 C2 -18.9(3) . . . . ?
N1 Ni1 N2 C16 -155.6(4) . . . . ?
N3 Ni1 N2 C16 24.0(4) . . . . ?
N1 Ni1 N2 C15 23.9(4) . . . . ?
N3 Ni1 N2 C15 -156.5(4) . . . . ?
N2 Ni1 N3 C17 -30.4(3) . . . . ?
O1 Ni1 N3 C17 149.8(3) . . . . ?
N2 Ni1 N3 C20 -143.3(4) . . . . ?
O1 Ni1 N3 C20 36.9(4) . . . . ?
N2 Ni1 N3 C21 92.8(3) . . . . ?
O1 Ni1 N3 C21 -87.0(3) . . . . ?
Ni1 O1 C1 O2 179.5(4) . . . . ?
Ni1 O1 C1 C2 3.4(5) . . . . ?
C3 N1 C2 C1 -157.1(5) . . . . ?
Ni1 N1 C2 C1 23.8(5) . . . . ?
C3 N1 C2 C28 81.3(6) . . . . ?
Ni1 N1 C2 C28 -97.8(4) . . . . ?
O2 C1 C2 N1 166.0(4) . . . . ?
O1 C1 C2 N1 -17.8(6) . . . . ?
O2 C1 C2 C28 -73.6(6) . . . . ?
O1 C1 C2 C28 102.5(5) . . . . ?
C2 N1 C3 C10 -173.7(5) . . . . ?
Ni1 N1 C3 C10 5.3(8) . . . . ?
C2 N1 C3 C4 9.2(7) . . . . ?
Ni1 N1 C3 C4 -171.8(4) . . . . ?
N1 C3 C4 C5 -108.1(6) . . . . ?
C10 C3 C4 C5 74.7(7) . . . . ?
N1 C3 C4 C9 73.2(7) . . . . ?
C10 C3 C4 C9 -104.0(6) . . . . ?
C9 C4 C5 C6 0.9(8) . . . . ?
C3 C4 C5 C6 -177.9(5) . . . . ?
C4 C5 C6 C7 0.3(8) . . . . ?
C5 C6 C7 C8 -1.8(9) . . . . ?
C6 C7 C8 C9 2.0(9) . . . . ?
C7 C8 C9 C4 -0.7(8) . . . . ?
C5 C4 C9 C8 -0.7(8) . . . . ?
C3 C4 C9 C8 178.1(5) . . . . ?
N1 C3 C10 C11 -173.3(5) . . . . ?
C4 C3 C10 C11 3.8(8) . . . . ?
N1 C3 C10 C15 8.3(9) . . . . ?
C4 C3 C10 C15 -174.6(5) . . . . ?
C15 C10 C11 C12 -0.6(8) . . . . ?
C3 C10 C11 C12 -179.1(5) . . . . ?
C10 C11 C12 C13 -0.8(8) . . . . ?
C11 C12 C13 C14 0.9(8) . . . . ?
C12 C13 C14 C15 0.5(8) . . . . ?
C13 C14 C15 N2 -179.8(5) . . . . ?
C13 C14 C15 C10 -1.9(8) . . . . ?
C16 N2 C15 C14 -20.5(7) . . . . ?
Ni1 N2 C15 C14 160.0(4) . . . . ?
C16 N2 C15 C10 161.7(5) . . . . ?
Ni1 N2 C15 C10 -17.8(7) . . . . ?
C11 C10 C15 C14 1.9(7) . . . . ?
C3 C10 C15 C14 -179.7(6) . . . . ?
C11 C10 C15 N2 179.8(4) . . . . ?
C3 C10 C15 N2 -1.8(8) . . . . ?
C15 N2 C16 O3 -11.0(8) . . . . ?
Ni1 N2 C16 O3 168.6(5) . . . . ?
C15 N2 C16 C17 170.3(4) . . . . ?
Ni1 N2 C16 C17 -10.2(5) . . . . ?
C20 N3 C17 C16 151.7(4) . . . . ?
C21 N3 C17 C16 -90.4(5) . . . . ?
Ni1 N3 C17 C16 31.3(4) . . . . ?
C20 N3 C17 C18 31.9(5) . . . . ?
C21 N3 C17 C18 149.8(4) . . . . ?
Ni1 N3 C17 C18 -88.5(4) . . . . ?
O3 C16 C17 N3 165.8(5) . . . . ?
N2 C16 C17 N3 -15.4(6) . . . . ?
O3 C16 C17 C18 -77.8(6) . . . . ?
N2 C16 C17 C18 101.1(5) . . . . ?
N3 C17 C18 C19 -8.2(5) . . . . ?
C16 C17 C18 C19 -128.3(5) . . . . ?
C17 C18 C19 C20 -18.0(6) . . . . ?
C17 N3 C20 C19 -44.4(5) . . . . ?
C21 N3 C20 C19 -165.8(4) . . . . ?
Ni1 N3 C20 C19 68.9(5) . . . . ?
C18 C19 C20 N3 37.9(5) . . . . ?
C17 N3 C21 C22 55.8(6) . . . . ?
C20 N3 C21 C22 170.9(4) . . . . ?
Ni1 N3 C21 C22 -62.0(5) . . . . ?
N3 C21 C22 C23 93.1(6) . . . . ?
N3 C21 C22 C27 -87.7(6) . . . . ?
C27 C22 C23 F1 -178.7(5) . . . . ?
C21 C22 C23 F1 0.6(8) . . . . ?
C27 C22 C23 C24 -0.4(8) . . . . ?
C21 C22 C23 C24 178.9(5) . . . . ?
F1 C23 C24 C25 -179.7(5) . . . . ?
C22 C23 C24 C25 2.0(9) . . . . ?
C23 C24 C25 C26 -1.2(10) . . . . ?
C24 C25 C26 C27 -1.1(9) . . . . ?
C25 C26 C27 C22 2.8(9) . . . . ?
C23 C22 C27 C26 -2.1(8) . . . . ?
C21 C22 C27 C26 178.7(5) . . . . ?
N1 C2 C28 C29 -170.3(4) . . . . ?
C1 C2 C28 C29 70.8(6) . . . . ?
C2 C28 C29 C30 68.7(6) . . . . ?
C28 C29 C30 C31 178.7(5) . . . . ?
C29 C30 C31 C32 119.7(9) . . . . ?
C35 O5 C33 O4 1.2(14) . . . . ?
C35 O5 C33 C34 172.8(9) . . . . ?
C33 O5 C35 C36 -131.4(10) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.628
_refine_diff_density_rms         0.069

_database_code_depnum_ccdc_archive 'CCDC 1020155'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_14086
_vrf_RINTA01_I                   
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: ...The crystal data was not the best due to crystal quality.
;
_vrf_PLAT020_I                   
;
PROBLEM: The value of Rint is greater than 0.12 .........      0.346       
RESPONSE: ...The crystal data was not the best due to crystal quality.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H38 F N3 Ni O3'
_chemical_formula_sum            'C35 H38 F N3 Ni O3'
_chemical_formula_weight         626.39

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'
F F 0.0171 0.0103 '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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_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                   9.165(10)
_cell_length_b                   13.957(14)
_cell_length_c                   23.73(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3035(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    632
_cell_measurement_theta_min      2.794
_cell_measurement_theta_max      28.156

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1320
_exptl_absorpt_coefficient_mu    0.686
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.320
_exptl_absorpt_correction_T_max  0.894
_exptl_absorpt_process_details   
;
absorption correction based on 3226 reflections(SADABS);Rint 0.1773 before
correction and 0.1327 after.
;

_exptl_special_details           
; 
 Atoms C32 and C33 of the chain are disordered and have been split.  
;

_diffrn_ambient_temperature      150(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 Apex 2000 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            23841
_diffrn_reflns_av_R_equivalents  0.3457
_diffrn_reflns_av_sigmaI/netI    0.2624
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         26.00
_reflns_number_total             5966
_reflns_number_gt                3231
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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 F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0229P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(3)
_chemical_absolute_configuration ,syn
_refine_ls_number_reflns         5966
_refine_ls_number_parameters     406
_refine_ls_number_restraints     447
_refine_ls_R_factor_all          0.1468
_refine_ls_R_factor_gt           0.0841
_refine_ls_wR_factor_ref         0.1662
_refine_ls_wR_factor_gt          0.1441
_refine_ls_goodness_of_fit_ref   0.871
_refine_ls_restrained_S_all      0.847
_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 0.81828(8) 0.32768(7) 0.83916(4) 0.0267(2) Uani 1 1 d U . .
F1 F 0.5808(4) 0.2738(3) 0.75939(18) 0.0468(12) Uani 1 1 d U . .
O1 O 0.8706(5) 0.4298(4) 0.7918(2) 0.0364(13) Uani 1 1 d U . .
O2 O 0.8306(5) 0.5845(4) 0.7764(2) 0.0331(12) Uani 1 1 d U . .
O3 O 0.8776(5) 0.0736(4) 0.9054(2) 0.0471(16) Uani 1 1 d U . .
N1 N 0.6903(6) 0.4130(4) 0.8745(2) 0.0253(12) Uani 1 1 d U . .
N2 N 0.7695(5) 0.2203(4) 0.8822(2) 0.0259(13) Uani 1 1 d U . .
N3 N 0.9491(6) 0.2448(4) 0.7973(3) 0.0332(10) Uani 1 1 d U . .
C1 C 0.8127(7) 0.5110(6) 0.8040(3) 0.0293(15) Uani 1 1 d U . .
C2 C 0.7236(6) 0.5138(5) 0.8581(2) 0.0198(14) Uani 1 1 d U . .
H2 H 0.6307 0.5497 0.8517 0.024 Uiso 1 1 calc R . .
C3 C 0.5799(7) 0.3909(6) 0.9064(3) 0.0282(16) Uani 1 1 d U . .
C4 C 0.4728(7) 0.4684(5) 0.9227(3) 0.0267(16) Uani 1 1 d U . .
C5 C 0.4639(7) 0.5018(5) 0.9781(3) 0.0289(17) Uani 1 1 d U . .
H5 H 0.5316 0.4809 1.0058 0.035 Uiso 1 1 calc R . .
C6 C 0.3526(7) 0.5667(5) 0.9919(3) 0.0326(18) Uani 1 1 d U . .
H6 H 0.3457 0.5906 1.0293 0.039 Uiso 1 1 calc R . .
C7 C 0.2552(7) 0.5959(6) 0.9526(3) 0.0356(19) Uani 1 1 d U . .
H7 H 0.1793 0.6386 0.9633 0.043 Uiso 1 1 calc R . .
C8 C 0.2632(7) 0.5649(6) 0.8970(3) 0.0357(19) Uani 1 1 d U . .
H8 H 0.1956 0.5868 0.8695 0.043 Uiso 1 1 calc R . .
C9 C 0.3739(6) 0.5006(5) 0.8829(3) 0.0299(17) Uani 1 1 d U . .
H9 H 0.3815 0.4785 0.8452 0.036 Uiso 1 1 calc R . .
C10 C 0.5525(7) 0.2926(5) 0.9263(3) 0.0242(15) Uani 1 1 d U . .
C11 C 0.4254(7) 0.2776(6) 0.9593(3) 0.0275(16) Uani 1 1 d U . .
H11 H 0.3622 0.3303 0.9660 0.033 Uiso 1 1 calc R . .
C12 C 0.3899(7) 0.1903(5) 0.9820(3) 0.0312(17) Uani 1 1 d U . .
H12 H 0.3048 0.1828 1.0045 0.037 Uiso 1 1 calc R . .
C13 C 0.4798(8) 0.1148(6) 0.9716(3) 0.040(2) Uani 1 1 d U . .
H13 H 0.4577 0.0541 0.9876 0.048 Uiso 1 1 calc R . .
C14 C 0.6013(8) 0.1243(6) 0.9387(3) 0.0383(19) Uani 1 1 d U . .
H14 H 0.6587 0.0692 0.9309 0.046 Uiso 1 1 calc R . .
C15 C 0.6441(7) 0.2130(5) 0.9159(3) 0.0256(16) Uani 1 1 d U . .
C16 C 0.8720(7) 0.1487(6) 0.8784(3) 0.0318(17) Uani 1 1 d U . .
C17 C 0.9944(6) 0.1680(5) 0.8383(3) 0.0275(14) Uani 1 1 d U . .
H17 H 1.0190 0.1080 0.8173 0.033 Uiso 1 1 calc R . .
C18 C 1.1317(7) 0.2060(6) 0.8687(3) 0.046(2) Uani 1 1 d U . .
H18A H 1.2130 0.1595 0.8658 0.056 Uiso 1 1 calc R . .
H18B H 1.1111 0.2183 0.9090 0.056 Uiso 1 1 calc R . .
C19 C 1.1694(7) 0.3003(5) 0.8376(3) 0.0358(11) Uani 1 1 d U . .
H19A H 1.1331 0.3566 0.8587 0.043 Uiso 1 1 calc R . .
H19B H 1.2761 0.3067 0.8322 0.043 Uiso 1 1 calc R . .
C20 C 1.0923(7) 0.2906(6) 0.7816(3) 0.0343(10) Uani 1 1 d U . .
H20A H 1.0769 0.3540 0.7639 0.041 Uiso 1 1 calc R . .
H20B H 1.1483 0.2493 0.7555 0.041 Uiso 1 1 calc R . .
C21 C 0.8757(7) 0.2098(5) 0.7460(3) 0.0331(17) Uani 1 1 d U . .
H21A H 0.9477 0.1746 0.7228 0.040 Uiso 1 1 calc R . .
H21B H 0.8424 0.2658 0.7238 0.040 Uiso 1 1 calc R . .
C22 C 0.7458(7) 0.1448(5) 0.7567(3) 0.0260(16) Uani 1 1 d U . .
C23 C 0.6049(7) 0.1767(6) 0.7628(3) 0.0315(16) Uani 1 1 d U . .
C24 C 0.4852(8) 0.1197(6) 0.7713(3) 0.0385(19) Uani 1 1 d U . .
H24 H 0.3900 0.1461 0.7740 0.046 Uiso 1 1 calc R . .
C25 C 0.5088(8) 0.0205(6) 0.7757(3) 0.0380(19) Uani 1 1 d U . .
H25 H 0.4290 -0.0216 0.7821 0.046 Uiso 1 1 calc R . .
C26 C 0.6462(7) -0.0151(6) 0.7707(3) 0.0371(18) Uani 1 1 d U . .
H26 H 0.6616 -0.0820 0.7748 0.044 Uiso 1 1 calc R . .
C27 C 0.7651(7) 0.0444(5) 0.7599(3) 0.0284(16) Uani 1 1 d U . .
H27 H 0.8593 0.0175 0.7547 0.034 Uiso 1 1 calc R . .
C28 C 0.8103(8) 0.5606(5) 0.9070(3) 0.0311(17) Uani 1 1 d U . .
H28A H 0.8993 0.5222 0.9140 0.037 Uiso 1 1 calc R . .
H28B H 0.7500 0.5583 0.9416 0.037 Uiso 1 1 calc R . .
C29 C 0.8564(7) 0.6671(6) 0.8960(3) 0.0363(17) Uani 1 1 d U . .
H29A H 0.9030 0.6920 0.9307 0.044 Uiso 1 1 calc R . .
H29B H 0.9314 0.6673 0.8660 0.044 Uiso 1 1 calc R . .
C30 C 0.7378(8) 0.7354(6) 0.8792(4) 0.049(2) Uani 1 1 d U B .
H30A H 0.7828 0.7988 0.8724 0.059 Uiso 1 1 calc R . .
H30B H 0.6965 0.7132 0.8429 0.059 Uiso 1 1 calc R . .
C31 C 0.6186(8) 0.7482(6) 0.9183(4) 0.063(3) Uani 1 1 d DU . .
H31A H 0.6547 0.7742 0.9545 0.076 Uiso 1 1 calc R A 1
H31B H 0.5692 0.6863 0.9256 0.076 Uiso 1 1 calc R A 1
C32A C 0.5124(17) 0.8198(13) 0.8898(5) 0.043(4) Uani 0.50 1 d PDU B 1
H32A H 0.5666 0.8780 0.8785 0.051 Uiso 0.50 1 calc PR B 1
H32B H 0.4709 0.7903 0.8554 0.051 Uiso 0.50 1 calc PR B 1
C32B C 0.5080(17) 0.8295(12) 0.9210(10) 0.071(5) Uani 0.50 1 d PDU B 2
H32C H 0.4645 0.8294 0.9592 0.085 Uiso 0.50 1 calc PR B 2
H32D H 0.5618 0.8905 0.9168 0.085 Uiso 0.50 1 calc PR B 2
C33A C 0.3884(12) 0.8476(9) 0.9299(5) 0.056(3) Uani 0.65 1 d PDU B 1
H33A H 0.3418 0.7890 0.9452 0.067 Uiso 0.65 1 calc PR B 1
H33B H 0.4280 0.8849 0.9619 0.067 Uiso 0.65 1 calc PR B 1
C33B C 0.3844(18) 0.8297(14) 0.8789(8) 0.046(5) Uani 0.35 1 d PDU B 2
H33C H 0.3364 0.7661 0.8778 0.055 Uiso 0.35 1 calc PR B 2
H33D H 0.4215 0.8447 0.8407 0.055 Uiso 0.35 1 calc PR B 2
C34 C 0.2755(10) 0.9073(8) 0.8984(5) 0.082(3) Uani 1 1 d DU . .
H34 H 0.3114 0.9656 0.8832 0.098 Uiso 1 1 calc R B 1
C35 C 0.1419(9) 0.8916(8) 0.8894(5) 0.077(3) Uani 1 1 d U B .
H35A H 0.0976 0.8348 0.9033 0.092 Uiso 1 1 calc R . .
H35B H 0.0856 0.9367 0.8687 0.092 Uiso 1 1 calc R . .


_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 1.868(6) . ?
Ni1 N1 1.870(5) . ?
Ni1 O1 1.876(5) . ?
Ni1 N3 1.940(6) . ?
F1 C23 1.376(9) . ?
O1 C1 1.284(8) . ?
O2 C1 1.230(8) . ?
O3 C16 1.229(9) . ?
N1 C3 1.301(8) . ?
N1 C2 1.491(8) . ?
N2 C16 1.374(9) . ?
N2 C15 1.404(7) . ?
N3 C21 1.474(9) . ?
N3 C17 1.505(9) . ?
N3 C20 1.506(8) . ?
C1 C2 1.523(9) . ?
C2 C28 1.551(9) . ?
C2 H2 1.0000 . ?
C3 C10 1.473(10) . ?
C3 C4 1.511(9) . ?
C4 C9 1.385(9) . ?
C4 C5 1.397(10) . ?
C5 C6 1.403(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.354(9) . ?
C6 H6 0.9500 . ?
C7 C8 1.391(10) . ?
C7 H7 0.9500 . ?
C8 C9 1.395(9) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C15 1.414(9) . ?
C10 C11 1.420(9) . ?
C11 C12 1.371(9) . ?
C11 H11 0.9500 . ?
C12 C13 1.362(9) . ?
C12 H12 0.9500 . ?
C13 C14 1.366(9) . ?
C13 H13 0.9500 . ?
C14 C15 1.407(10) . ?
C14 H14 0.9500 . ?
C16 C17 1.496(9) . ?
C17 C18 1.545(9) . ?
C17 H17 1.0000 . ?
C18 C19 1.549(10) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.510(10) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.519(9) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.373(9) . ?
C22 C27 1.414(10) . ?
C23 C24 1.370(10) . ?
C24 C25 1.405(11) . ?
C24 H24 0.9500 . ?
C25 C26 1.358(10) . ?
C25 H25 0.9500 . ?
C26 C27 1.394(9) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C29 1.567(10) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.500(10) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.444(11) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32B 1.523(9) . ?
C31 C32A 1.550(9) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32A C33A 1.532(9) . ?
C32A H32A 0.9900 . ?
C32A H32B 0.9900 . ?
C32B C33B 1.511(10) . ?
C32B H32C 0.9900 . ?
C32B H32D 0.9900 . ?
C33A C34 1.525(9) . ?
C33A H33A 0.9900 . ?
C33A H33B 0.9900 . ?
C33B C34 1.544(10) . ?
C33B H33C 0.9900 . ?
C33B H33D 0.9900 . ?
C34 C35 1.262(10) . ?
C34 H34 0.9500 . ?
C35 H35A 0.9500 . ?
C35 H35B 0.9500 . ?

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 96.6(3) . . ?
N2 Ni1 O1 176.0(2) . . ?
N1 Ni1 O1 86.9(2) . . ?
N2 Ni1 N3 87.1(3) . . ?
N1 Ni1 N3 175.7(3) . . ?
O1 Ni1 N3 89.3(2) . . ?
C1 O1 Ni1 115.5(5) . . ?
C3 N1 C2 122.3(6) . . ?
C3 N1 Ni1 126.8(5) . . ?
C2 N1 Ni1 110.8(4) . . ?
C16 N2 C15 122.9(6) . . ?
C16 N2 Ni1 112.6(5) . . ?
C15 N2 Ni1 124.4(5) . . ?
C21 N3 C17 115.0(6) . . ?
C21 N3 C20 109.5(5) . . ?
C17 N3 C20 102.8(5) . . ?
C21 N3 Ni1 109.8(4) . . ?
C17 N3 Ni1 105.3(4) . . ?
C20 N3 Ni1 114.3(5) . . ?
O2 C1 O1 124.2(7) . . ?
O2 C1 C2 120.0(7) . . ?
O1 C1 C2 115.7(6) . . ?
N1 C2 C1 107.8(5) . . ?
N1 C2 C28 107.9(5) . . ?
C1 C2 C28 111.5(5) . . ?
N1 C2 H2 109.8 . . ?
C1 C2 H2 109.8 . . ?
C28 C2 H2 109.8 . . ?
N1 C3 C10 122.6(7) . . ?
N1 C3 C4 119.0(6) . . ?
C10 C3 C4 118.3(6) . . ?
C9 C4 C5 119.7(7) . . ?
C9 C4 C3 118.9(7) . . ?
C5 C4 C3 121.2(6) . . ?
C4 C5 C6 118.5(7) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C7 C6 C5 120.9(7) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 121.7(7) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C7 C8 C9 117.8(7) . . ?
C7 C8 H8 121.1 . . ?
C9 C8 H8 121.1 . . ?
C4 C9 C8 121.4(7) . . ?
C4 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C15 C10 C11 117.9(7) . . ?
C15 C10 C3 125.1(6) . . ?
C11 C10 C3 117.0(6) . . ?
C12 C11 C10 122.9(7) . . ?
C12 C11 H11 118.6 . . ?
C10 C11 H11 118.6 . . ?
C13 C12 C11 118.2(7) . . ?
C13 C12 H12 120.9 . . ?
C11 C12 H12 120.9 . . ?
C12 C13 C14 121.4(8) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C13 C14 C15 122.2(7) . . ?
C13 C14 H14 118.9 . . ?
C15 C14 H14 118.9 . . ?
N2 C15 C14 120.7(6) . . ?
N2 C15 C10 121.9(7) . . ?
C14 C15 C10 117.3(6) . . ?
O3 C16 N2 127.9(7) . . ?
O3 C16 C17 117.0(6) . . ?
N2 C16 C17 115.0(7) . . ?
C16 C17 N3 109.5(5) . . ?
C16 C17 C18 112.0(6) . . ?
N3 C17 C18 106.4(6) . . ?
C16 C17 H17 109.7 . . ?
N3 C17 H17 109.7 . . ?
C18 C17 H17 109.7 . . ?
C17 C18 C19 104.5(6) . . ?
C17 C18 H18A 110.9 . . ?
C19 C18 H18A 110.9 . . ?
C17 C18 H18B 110.9 . . ?
C19 C18 H18B 110.9 . . ?
H18A C18 H18B 108.9 . . ?
C20 C19 C18 103.8(6) . . ?
C20 C19 H19A 111.0 . . ?
C18 C19 H19A 111.0 . . ?
C20 C19 H19B 111.0 . . ?
C18 C19 H19B 111.0 . . ?
H19A C19 H19B 109.0 . . ?
N3 C20 C19 103.2(6) . . ?
N3 C20 H20A 111.1 . . ?
C19 C20 H20A 111.1 . . ?
N3 C20 H20B 111.1 . . ?
C19 C20 H20B 111.1 . . ?
H20A C20 H20B 109.1 . . ?
N3 C21 C22 114.7(6) . . ?
N3 C21 H21A 108.6 . . ?
C22 C21 H21A 108.6 . . ?
N3 C21 H21B 108.6 . . ?
C22 C21 H21B 108.6 . . ?
H21A C21 H21B 107.6 . . ?
C23 C22 C27 115.7(7) . . ?
C23 C22 C21 124.1(7) . . ?
C27 C22 C21 120.2(6) . . ?
C24 C23 C22 125.4(8) . . ?
C24 C23 F1 116.9(6) . . ?
C22 C23 F1 117.6(7) . . ?
C23 C24 C25 117.4(7) . . ?
C23 C24 H24 121.3 . . ?
C25 C24 H24 121.3 . . ?
C26 C25 C24 119.7(7) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C25 C26 C27 121.5(8) . . ?
C25 C26 H26 119.2 . . ?
C27 C26 H26 119.2 . . ?
C26 C27 C22 120.1(7) . . ?
C26 C27 H27 119.9 . . ?
C22 C27 H27 119.9 . . ?
C2 C28 C29 114.4(6) . . ?
C2 C28 H28A 108.7 . . ?
C29 C28 H28A 108.7 . . ?
C2 C28 H28B 108.7 . . ?
C29 C28 H28B 108.7 . . ?
H28A C28 H28B 107.6 . . ?
C30 C29 C28 116.8(6) . . ?
C30 C29 H29A 108.1 . . ?
C28 C29 H29A 108.1 . . ?
C30 C29 H29B 108.1 . . ?
C28 C29 H29B 108.1 . . ?
H29A C29 H29B 107.3 . . ?
C31 C30 C29 117.2(7) . . ?
C31 C30 H30A 108.0 . . ?
C29 C30 H30A 108.0 . . ?
C31 C30 H30B 108.0 . . ?
C29 C30 H30B 108.0 . . ?
H30A C30 H30B 107.3 . . ?
C30 C31 C32B 128.5(13) . . ?
C30 C31 C32A 105.9(8) . . ?
C30 C31 H31A 110.5 . . ?
C32B C31 H31A 84.9 . . ?
C32A C31 H31A 110.5 . . ?
C30 C31 H31B 110.5 . . ?
C32B C31 H31B 109.7 . . ?
C32A C31 H31B 110.5 . . ?
H31A C31 H31B 108.7 . . ?
C33A C32A C31 111.0(8) . . ?
C33A C32A H32A 109.4 . . ?
C31 C32A H32A 109.4 . . ?
C33A C32A H32B 109.4 . . ?
C31 C32A H32B 109.4 . . ?
H32A C32A H32B 108.0 . . ?
C33B C32B C31 118.2(12) . . ?
C33B C32B H32C 107.8 . . ?
C31 C32B H32C 107.8 . . ?
C33B C32B H32D 107.8 . . ?
C31 C32B H32D 107.8 . . ?
H32C C32B H32D 107.1 . . ?
C34 C33A C32A 109.7(9) . . ?
C34 C33A H33A 109.7 . . ?
C32A C33A H33A 109.7 . . ?
C34 C33A H33B 109.7 . . ?
C32A C33A H33B 109.7 . . ?
H33A C33A H33B 108.2 . . ?
C32B C33B C34 106.7(10) . . ?
C32B C33B H33C 110.4 . . ?
C34 C33B H33C 110.4 . . ?
C32B C33B H33D 110.4 . . ?
C34 C33B H33D 110.4 . . ?
H33C C33B H33D 108.6 . . ?
C35 C34 C33A 130.4(11) . . ?
C35 C34 C33B 117.1(12) . . ?
C33A C34 C33B 47.6(8) . . ?
C35 C34 H34 114.8 . . ?
C33A C34 H34 114.8 . . ?
C33B C34 H34 105.2 . . ?
C34 C35 H35A 120.0 . . ?
C34 C35 H35B 120.0 . . ?
H35A C35 H35B 120.0 . . ?

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 O1 C1 4.8(5) . . . . ?
N3 Ni1 O1 C1 -177.3(5) . . . . ?
N2 Ni1 N1 C3 -16.4(6) . . . . ?
O1 Ni1 N1 C3 161.7(6) . . . . ?
N2 Ni1 N1 C2 167.8(4) . . . . ?
O1 Ni1 N1 C2 -14.1(4) . . . . ?
N1 Ni1 N2 C16 -162.9(5) . . . . ?
N3 Ni1 N2 C16 19.3(5) . . . . ?
N1 Ni1 N2 C15 15.8(5) . . . . ?
N3 Ni1 N2 C15 -162.0(5) . . . . ?
N2 Ni1 N3 C21 95.7(5) . . . . ?
O1 Ni1 N3 C21 -82.5(5) . . . . ?
N2 Ni1 N3 C17 -28.7(4) . . . . ?
O1 Ni1 N3 C17 153.1(4) . . . . ?
N2 Ni1 N3 C20 -140.8(5) . . . . ?
O1 Ni1 N3 C20 41.0(5) . . . . ?
Ni1 O1 C1 O2 -177.3(6) . . . . ?
Ni1 O1 C1 C2 6.0(7) . . . . ?
C3 N1 C2 C1 -156.7(6) . . . . ?
Ni1 N1 C2 C1 19.4(5) . . . . ?
C3 N1 C2 C28 82.7(7) . . . . ?
Ni1 N1 C2 C28 -101.2(5) . . . . ?
O2 C1 C2 N1 166.5(6) . . . . ?
O1 C1 C2 N1 -16.7(7) . . . . ?
O2 C1 C2 C28 -75.2(8) . . . . ?
O1 C1 C2 C28 101.7(7) . . . . ?
C2 N1 C3 C10 -175.2(6) . . . . ?
Ni1 N1 C3 C10 9.4(9) . . . . ?
C2 N1 C3 C4 6.3(9) . . . . ?
Ni1 N1 C3 C4 -169.1(5) . . . . ?
N1 C3 C4 C9 75.0(8) . . . . ?
C10 C3 C4 C9 -103.5(8) . . . . ?
N1 C3 C4 C5 -110.6(8) . . . . ?
C10 C3 C4 C5 70.9(9) . . . . ?
C9 C4 C5 C6 0.7(10) . . . . ?
C3 C4 C5 C6 -173.7(6) . . . . ?
C4 C5 C6 C7 0.6(11) . . . . ?
C5 C6 C7 C8 -1.7(11) . . . . ?
C6 C7 C8 C9 1.4(11) . . . . ?
C5 C4 C9 C8 -1.0(10) . . . . ?
C3 C4 C9 C8 173.5(6) . . . . ?
C7 C8 C9 C4 0.0(11) . . . . ?
N1 C3 C10 C15 3.3(11) . . . . ?
C4 C3 C10 C15 -178.3(6) . . . . ?
N1 C3 C10 C11 -177.9(6) . . . . ?
C4 C3 C10 C11 0.5(9) . . . . ?
C15 C10 C11 C12 1.2(10) . . . . ?
C3 C10 C11 C12 -177.7(6) . . . . ?
C10 C11 C12 C13 -1.0(11) . . . . ?
C11 C12 C13 C14 -1.1(11) . . . . ?
C12 C13 C14 C15 3.0(12) . . . . ?
C16 N2 C15 C14 -13.2(9) . . . . ?
Ni1 N2 C15 C14 168.2(5) . . . . ?
C16 N2 C15 C10 169.7(6) . . . . ?
Ni1 N2 C15 C10 -8.9(8) . . . . ?
C13 C14 C15 N2 -180.0(6) . . . . ?
C13 C14 C15 C10 -2.7(11) . . . . ?
C11 C10 C15 N2 177.9(6) . . . . ?
C3 C10 C15 N2 -3.4(10) . . . . ?
C11 C10 C15 C14 0.7(9) . . . . ?
C3 C10 C15 C14 179.4(7) . . . . ?
C15 N2 C16 O3 -5.7(11) . . . . ?
Ni1 N2 C16 O3 173.0(7) . . . . ?
C15 N2 C16 C17 177.3(5) . . . . ?
Ni1 N2 C16 C17 -4.0(7) . . . . ?
O3 C16 C17 N3 163.1(6) . . . . ?
N2 C16 C17 N3 -19.6(8) . . . . ?
O3 C16 C17 C18 -79.2(9) . . . . ?
N2 C16 C17 C18 98.1(7) . . . . ?
C21 N3 C17 C16 -88.9(7) . . . . ?
C20 N3 C17 C16 152.1(6) . . . . ?
Ni1 N3 C17 C16 32.1(6) . . . . ?
C21 N3 C17 C18 149.9(5) . . . . ?
C20 N3 C17 C18 31.0(7) . . . . ?
Ni1 N3 C17 C18 -89.1(5) . . . . ?
C16 C17 C18 C19 -126.2(7) . . . . ?
N3 C17 C18 C19 -6.7(7) . . . . ?
C17 C18 C19 C20 -20.1(7) . . . . ?
C21 N3 C20 C19 -166.7(6) . . . . ?
C17 N3 C20 C19 -44.0(7) . . . . ?
Ni1 N3 C20 C19 69.6(6) . . . . ?
C18 C19 C20 N3 39.7(7) . . . . ?
C17 N3 C21 C22 53.1(7) . . . . ?
C20 N3 C21 C22 168.2(6) . . . . ?
Ni1 N3 C21 C22 -65.5(7) . . . . ?
N3 C21 C22 C23 90.1(8) . . . . ?
N3 C21 C22 C27 -91.2(8) . . . . ?
C27 C22 C23 C24 -0.3(11) . . . . ?
C21 C22 C23 C24 178.5(7) . . . . ?
C27 C22 C23 F1 -179.3(5) . . . . ?
C21 C22 C23 F1 -0.6(10) . . . . ?
C22 C23 C24 C25 1.9(11) . . . . ?
F1 C23 C24 C25 -179.1(6) . . . . ?
C23 C24 C25 C26 -0.9(11) . . . . ?
C24 C25 C26 C27 -1.6(11) . . . . ?
C25 C26 C27 C22 3.3(10) . . . . ?
C23 C22 C27 C26 -2.3(10) . . . . ?
C21 C22 C27 C26 178.9(6) . . . . ?
N1 C2 C28 C29 179.1(5) . . . . ?
C1 C2 C28 C29 60.8(8) . . . . ?
C2 C28 C29 C30 53.0(9) . . . . ?
C28 C29 C30 C31 59.8(9) . . . . ?
C29 C30 C31 C32B 161.6(10) . . . . ?
C29 C30 C31 C32A -178.8(10) . . . . ?
C30 C31 C32A C33A -174.1(12) . . . . ?
C32B C31 C32A C33A -28(2) . . . . ?
C30 C31 C32B C33B 77(2) . . . . ?
C32A C31 C32B C33B 34.6(19) . . . . ?
C31 C32A C33A C34 -172.6(12) . . . . ?
C31 C32B C33B C34 169.4(17) . . . . ?
C32A C33A C34 C35 119.4(17) . . . . ?
C32A C33A C34 C33B 27.5(15) . . . . ?
C32B C33B C34 C35 -146.2(17) . . . . ?
C32B C33B C34 C33A -25.0(13) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.681
_refine_diff_density_min         -0.701
_refine_diff_density_rms         0.103

_database_code_depnum_ccdc_archive 'CCDC 1020156'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_14074

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H34 F N3 Ni O3'
_chemical_formula_sum            'C33 H34 F N3 Ni O3'
_chemical_formula_weight         598.34

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'
F F 0.0171 0.0103 '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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2

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

_cell_length_a                   11.8230(15)
_cell_length_b                   25.123(3)
_cell_length_c                   9.6587(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2869.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1010
_cell_measurement_theta_min      2.259
_cell_measurement_theta_max      23.324

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1256
_exptl_absorpt_coefficient_mu    0.722
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.681
_exptl_absorpt_correction_T_max  0.894
_exptl_absorpt_process_details   
;
absorption correction based on 3645 reflections(SADABS);Rint 0.1180 before
correction and 0.0646 after.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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 Apex 2000 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            22656
_diffrn_reflns_av_R_equivalents  0.1516
_diffrn_reflns_av_sigmaI/netI    0.1800
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.62
_diffrn_reflns_theta_max         26.00
_reflns_number_total             5627
_reflns_number_gt                3473
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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 F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.042(17)
_chemical_absolute_configuration ,syn
_refine_ls_number_reflns         5627
_refine_ls_number_parameters     371
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.0836
_refine_ls_wR_factor_gt          0.0728
_refine_ls_goodness_of_fit_ref   0.779
_refine_ls_restrained_S_all      0.779
_refine_ls_shift/su_max          0.002
_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 0.30595(5) 0.32667(2) 0.67471(7) 0.02181(15) Uani 1 1 d . . .
F1 F 0.2157(2) 0.24757(11) 0.8808(3) 0.0435(9) Uani 1 1 d . . .
O1 O 0.1712(2) 0.31907(12) 0.5829(3) 0.0284(9) Uani 1 1 d . . .
O2 O 0.0331(3) 0.36721(13) 0.4903(4) 0.0468(11) Uani 1 1 d . . .
O3 O 0.6330(3) 0.31240(12) 0.7207(3) 0.0315(10) Uani 1 1 d . . .
N1 N 0.2475(3) 0.39064(15) 0.7484(4) 0.0189(10) Uani 1 1 d . . .
N2 N 0.4425(3) 0.33101(16) 0.7628(4) 0.0208(10) Uani 1 1 d . . .
N3 N 0.3696(3) 0.26432(15) 0.5811(4) 0.0223(10) Uani 1 1 d . . .
C1 C 0.1136(4) 0.3621(2) 0.5693(6) 0.0288(13) Uani 1 1 d . . .
C2 C 0.1477(4) 0.40947(18) 0.6635(6) 0.0223(12) Uani 1 1 d . . .
C3 C 0.2896(4) 0.41770(17) 0.8483(5) 0.0234(12) Uani 1 1 d . . .
C4 C 0.2476(4) 0.47195(19) 0.8932(5) 0.0253(13) Uani 1 1 d . . .
C5 C 0.2943(4) 0.51683(17) 0.8349(5) 0.0296(12) Uani 1 1 d . . .
H5 H 0.3490 0.5134 0.7635 0.036 Uiso 1 1 calc R . .
C6 C 0.2617(5) 0.5676(2) 0.8800(6) 0.0451(18) Uani 1 1 d . . .
H6 H 0.2921 0.5986 0.8379 0.054 Uiso 1 1 calc R . .
C7 C 0.1846(5) 0.5716(2) 0.9869(7) 0.0454(17) Uani 1 1 d . . .
H7 H 0.1621 0.6057 1.0188 0.055 Uiso 1 1 calc R . .
C8 C 0.1398(4) 0.5266(2) 1.0481(6) 0.0442(17) Uani 1 1 d . . .
H8 H 0.0878 0.5300 1.1227 0.053 Uiso 1 1 calc R . .
C9 C 0.1704(4) 0.47656(19) 1.0009(6) 0.0333(14) Uani 1 1 d . . .
H9 H 0.1389 0.4456 1.0420 0.040 Uiso 1 1 calc R . .
C10 C 0.3877(4) 0.39882(19) 0.9305(5) 0.0236(12) Uani 1 1 d . . .
C11 C 0.4121(4) 0.4244(2) 1.0575(6) 0.0325(14) Uani 1 1 d . . .
H11 H 0.3675 0.4541 1.0846 0.039 Uiso 1 1 calc R . .
C12 C 0.4982(4) 0.40793(19) 1.1433(5) 0.0310(14) Uani 1 1 d . . .
H12 H 0.5132 0.4261 1.2276 0.037 Uiso 1 1 calc R . .
C13 C 0.5622(4) 0.36456(19) 1.1047(5) 0.0290(14) Uani 1 1 d . . .
H13 H 0.6201 0.3520 1.1646 0.035 Uiso 1 1 calc R . .
C14 C 0.5436(4) 0.33951(19) 0.9821(5) 0.0257(13) Uani 1 1 d . . .
H14 H 0.5888 0.3096 0.9582 0.031 Uiso 1 1 calc R . .
C15 C 0.4592(4) 0.35662(18) 0.8894(5) 0.0212(12) Uani 1 1 d . . .
C16 C 0.5316(4) 0.30758(17) 0.6944(5) 0.0213(12) Uani 1 1 d . . .
C17 C 0.4938(4) 0.27490(18) 0.5729(5) 0.0183(12) Uani 1 1 d . . .
H17 H 0.5355 0.2403 0.5727 0.022 Uiso 1 1 calc R . .
C18 C 0.5111(4) 0.30282(19) 0.4332(5) 0.0346(15) Uani 1 1 d . . .
H18A H 0.5654 0.2828 0.3751 0.042 Uiso 1 1 calc R . .
H18B H 0.5402 0.3394 0.4469 0.042 Uiso 1 1 calc R . .
C19 C 0.3938(4) 0.30408(18) 0.3649(5) 0.0304(14) Uani 1 1 d . . .
H19A H 0.3553 0.3385 0.3818 0.037 Uiso 1 1 calc R . .
H19B H 0.3992 0.2979 0.2639 0.037 Uiso 1 1 calc R . .
C20 C 0.3329(4) 0.25901(17) 0.4358(5) 0.0262(13) Uani 1 1 d . . .
H20A H 0.2499 0.2629 0.4273 0.031 Uiso 1 1 calc R . .
H20B H 0.3558 0.2242 0.3969 0.031 Uiso 1 1 calc R . .
C21 C 0.3449(4) 0.21279(16) 0.6570(5) 0.0233(12) Uani 1 1 d . . .
H21A H 0.2621 0.2070 0.6568 0.028 Uiso 1 1 calc R . .
H21B H 0.3797 0.1832 0.6046 0.028 Uiso 1 1 calc R . .
C22 C 0.3856(4) 0.21012(17) 0.8027(5) 0.0211(12) Uani 1 1 d . . .
C23 C 0.3197(4) 0.22681(18) 0.9113(6) 0.0279(13) Uani 1 1 d . . .
C24 C 0.3508(5) 0.2234(2) 1.0466(6) 0.0366(15) Uani 1 1 d . . .
H24 H 0.3006 0.2344 1.1180 0.044 Uiso 1 1 calc R . .
C25 C 0.4562(5) 0.20387(19) 1.0779(6) 0.0411(16) Uani 1 1 d . . .
H25 H 0.4812 0.2023 1.1713 0.049 Uiso 1 1 calc R . .
C26 C 0.5262(5) 0.18623(19) 0.9706(6) 0.0349(14) Uani 1 1 d . . .
H26 H 0.5989 0.1723 0.9915 0.042 Uiso 1 1 calc R . .
C27 C 0.4907(4) 0.18879(16) 0.8349(6) 0.0295(13) Uani 1 1 d . . .
H27 H 0.5383 0.1759 0.7630 0.035 Uiso 1 1 calc R . .
C28 C 0.1772(4) 0.45633(17) 0.5684(5) 0.0273(13) Uani 1 1 d . . .
H28A H 0.1122 0.4626 0.5059 0.033 Uiso 1 1 calc R . .
H28B H 0.1860 0.4885 0.6266 0.033 Uiso 1 1 calc R . .
C29 C 0.2830(5) 0.45054(19) 0.4799(6) 0.0410(16) Uani 1 1 d . . .
H29A H 0.2753 0.4187 0.4204 0.049 Uiso 1 1 calc R . .
H29B H 0.3492 0.4451 0.5410 0.049 Uiso 1 1 calc R . .
C30 C 0.3038(5) 0.50004(19) 0.3875(5) 0.0433(15) Uani 1 1 d . . .
H30A H 0.3681 0.4927 0.3247 0.052 Uiso 1 1 calc R . .
H30B H 0.2360 0.5063 0.3295 0.052 Uiso 1 1 calc R . .
C31 C 0.3287(5) 0.5493(2) 0.4693(6) 0.0387(16) Uani 1 1 d . . .
H31 H 0.4010 0.5520 0.5116 0.046 Uiso 1 1 calc R . .
C32 C 0.2582(5) 0.5888(2) 0.4865(7) 0.0539(19) Uani 1 1 d . . .
H32A H 0.1852 0.5874 0.4457 0.065 Uiso 1 1 calc R . .
H32B H 0.2800 0.6188 0.5400 0.065 Uiso 1 1 calc R . .
C33 C 0.0416(4) 0.4232(2) 0.7492(5) 0.0366(15) Uani 1 1 d . . .
H33A H 0.0476 0.4597 0.7839 0.055 Uiso 1 1 calc R . .
H33B H 0.0354 0.3985 0.8275 0.055 Uiso 1 1 calc R . .
H33C H -0.0258 0.4200 0.6906 0.055 Uiso 1 1 calc R . .


_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 1.829(4) . ?
Ni1 O1 1.833(3) . ?
Ni1 N1 1.889(4) . ?
Ni1 N3 1.959(4) . ?
F1 C23 1.368(5) . ?
O1 C1 1.285(5) . ?
O2 C1 1.227(6) . ?
O3 C16 1.231(5) . ?
N1 C3 1.282(5) . ?
N1 C2 1.512(5) . ?
N2 C16 1.375(5) . ?
N2 C15 1.396(5) . ?
N3 C20 1.475(5) . ?
N3 C17 1.494(5) . ?
N3 C21 1.516(5) . ?
C1 C2 1.551(6) . ?
C2 C28 1.533(6) . ?
C2 C33 1.542(6) . ?
C3 C10 1.483(6) . ?
C3 C4 1.514(6) . ?
C4 C5 1.375(6) . ?
C4 C9 1.389(6) . ?
C5 C6 1.402(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.381(8) . ?
C6 H6 0.9500 . ?
C7 C8 1.381(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(6) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C15 1.413(6) . ?
C10 C11 1.415(7) . ?
C11 C12 1.376(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.378(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.359(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.408(6) . ?
C14 H14 0.9500 . ?
C16 C17 1.500(6) . ?
C17 C18 1.535(6) . ?
C17 H17 1.0000 . ?
C18 C19 1.536(6) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.506(6) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.489(6) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.372(6) . ?
C22 C27 1.389(6) . ?
C23 C24 1.360(7) . ?
C24 C25 1.373(7) . ?
C24 H24 0.9500 . ?
C25 C26 1.398(7) . ?
C25 H25 0.9500 . ?
C26 C27 1.378(7) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C29 1.521(6) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.551(6) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.497(7) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.306(6) . ?
C31 H31 0.9500 . ?
C32 H32A 0.9500 . ?
C32 H32B 0.9500 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 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
N2 Ni1 O1 177.13(17) . . ?
N2 Ni1 N1 95.58(17) . . ?
O1 Ni1 N1 87.28(15) . . ?
N2 Ni1 N3 85.59(16) . . ?
O1 Ni1 N3 91.58(15) . . ?
N1 Ni1 N3 174.23(17) . . ?
C1 O1 Ni1 115.0(3) . . ?
C3 N1 C2 123.1(4) . . ?
C3 N1 Ni1 126.4(3) . . ?
C2 N1 Ni1 110.3(3) . . ?
C16 N2 C15 120.7(4) . . ?
C16 N2 Ni1 115.3(3) . . ?
C15 N2 Ni1 124.1(3) . . ?
C20 N3 C17 104.7(4) . . ?
C20 N3 C21 109.0(3) . . ?
C17 N3 C21 111.5(3) . . ?
C20 N3 Ni1 113.5(3) . . ?
C17 N3 Ni1 105.1(3) . . ?
C21 N3 Ni1 112.7(3) . . ?
O2 C1 O1 124.2(5) . . ?
O2 C1 C2 119.2(5) . . ?
O1 C1 C2 116.6(5) . . ?
N1 C2 C28 112.8(4) . . ?
N1 C2 C33 114.4(4) . . ?
C28 C2 C33 109.6(4) . . ?
N1 C2 C1 106.3(4) . . ?
C28 C2 C1 107.3(4) . . ?
C33 C2 C1 105.9(4) . . ?
N1 C3 C10 122.5(4) . . ?
N1 C3 C4 124.4(4) . . ?
C10 C3 C4 113.0(4) . . ?
C5 C4 C9 120.1(5) . . ?
C5 C4 C3 119.3(5) . . ?
C9 C4 C3 120.3(5) . . ?
C4 C5 C6 120.6(5) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 118.6(5) . . ?
C7 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C6 C7 C8 121.0(5) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C7 C8 C9 120.0(6) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C4 119.6(5) . . ?
C8 C9 H9 120.2 . . ?
C4 C9 H9 120.2 . . ?
C15 C10 C11 117.5(5) . . ?
C15 C10 C3 123.9(5) . . ?
C11 C10 C3 118.6(5) . . ?
C12 C11 C10 122.4(5) . . ?
C12 C11 H11 118.8 . . ?
C10 C11 H11 118.8 . . ?
C11 C12 C13 118.8(5) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C14 C13 C12 120.9(5) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 121.8(5) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
N2 C15 C14 121.1(4) . . ?
N2 C15 C10 120.5(5) . . ?
C14 C15 C10 118.3(5) . . ?
O3 C16 N2 127.2(5) . . ?
O3 C16 C17 120.3(4) . . ?
N2 C16 C17 112.5(4) . . ?
N3 C17 C16 110.4(4) . . ?
N3 C17 C18 105.0(4) . . ?
C16 C17 C18 113.5(4) . . ?
N3 C17 H17 109.3 . . ?
C16 C17 H17 109.3 . . ?
C18 C17 H17 109.3 . . ?
C17 C18 C19 105.5(4) . . ?
C17 C18 H18A 110.6 . . ?
C19 C18 H18A 110.6 . . ?
C17 C18 H18B 110.6 . . ?
C19 C18 H18B 110.6 . . ?
H18A C18 H18B 108.8 . . ?
C20 C19 C18 102.8(4) . . ?
C20 C19 H19A 111.2 . . ?
C18 C19 H19A 111.2 . . ?
C20 C19 H19B 111.2 . . ?
C18 C19 H19B 111.2 . . ?
H19A C19 H19B 109.1 . . ?
N3 C20 C19 102.9(4) . . ?
N3 C20 H20A 111.2 . . ?
C19 C20 H20A 111.2 . . ?
N3 C20 H20B 111.2 . . ?
C19 C20 H20B 111.2 . . ?
H20A C20 H20B 109.1 . . ?
C22 C21 N3 115.7(4) . . ?
C22 C21 H21A 108.4 . . ?
N3 C21 H21A 108.4 . . ?
C22 C21 H21B 108.4 . . ?
N3 C21 H21B 108.4 . . ?
H21A C21 H21B 107.4 . . ?
C23 C22 C27 117.1(5) . . ?
C23 C22 C21 121.7(5) . . ?
C27 C22 C21 121.2(5) . . ?
C24 C23 F1 118.3(5) . . ?
C24 C23 C22 124.2(5) . . ?
F1 C23 C22 117.5(5) . . ?
C23 C24 C25 118.6(6) . . ?
C23 C24 H24 120.7 . . ?
C25 C24 H24 120.7 . . ?
C24 C25 C26 119.2(6) . . ?
C24 C25 H25 120.4 . . ?
C26 C25 H25 120.4 . . ?
C27 C26 C25 120.7(5) . . ?
C27 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C26 C27 C22 120.2(5) . . ?
C26 C27 H27 119.9 . . ?
C22 C27 H27 119.9 . . ?
C29 C28 C2 116.7(4) . . ?
C29 C28 H28A 108.1 . . ?
C2 C28 H28A 108.1 . . ?
C29 C28 H28B 108.1 . . ?
C2 C28 H28B 108.1 . . ?
H28A C28 H28B 107.3 . . ?
C28 C29 C30 112.2(4) . . ?
C28 C29 H29A 109.2 . . ?
C30 C29 H29A 109.2 . . ?
C28 C29 H29B 109.2 . . ?
C30 C29 H29B 109.2 . . ?
H29A C29 H29B 107.9 . . ?
C31 C30 C29 112.9(4) . . ?
C31 C30 H30A 109.0 . . ?
C29 C30 H30A 109.0 . . ?
C31 C30 H30B 109.0 . . ?
C29 C30 H30B 109.0 . . ?
H30A C30 H30B 107.8 . . ?
C32 C31 C30 124.7(6) . . ?
C32 C31 H31 117.6 . . ?
C30 C31 H31 117.6 . . ?
C31 C32 H32A 120.0 . . ?
C31 C32 H32B 120.0 . . ?
H32A C32 H32B 120.0 . . ?
C2 C33 H33A 109.5 . . ?
C2 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C2 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 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 O1 C1 19.8(4) . . . . ?
N3 Ni1 O1 C1 -154.6(4) . . . . ?
N2 Ni1 N1 C3 -12.3(4) . . . . ?
O1 Ni1 N1 C3 167.5(4) . . . . ?
N2 Ni1 N1 C2 162.2(3) . . . . ?
O1 Ni1 N1 C2 -18.0(3) . . . . ?
N1 Ni1 N2 C16 -150.6(3) . . . . ?
N3 Ni1 N2 C16 23.8(3) . . . . ?
N1 Ni1 N2 C15 28.4(4) . . . . ?
N3 Ni1 N2 C15 -157.2(4) . . . . ?
N2 Ni1 N3 C20 -143.9(3) . . . . ?
O1 Ni1 N3 C20 36.6(3) . . . . ?
N2 Ni1 N3 C17 -30.0(3) . . . . ?
O1 Ni1 N3 C17 150.4(3) . . . . ?
N2 Ni1 N3 C21 91.6(3) . . . . ?
O1 Ni1 N3 C21 -87.9(3) . . . . ?
Ni1 O1 C1 O2 165.9(4) . . . . ?
Ni1 O1 C1 C2 -16.0(6) . . . . ?
C3 N1 C2 C28 70.7(6) . . . . ?
Ni1 N1 C2 C28 -104.0(4) . . . . ?
C3 N1 C2 C33 -55.5(6) . . . . ?
Ni1 N1 C2 C33 129.8(3) . . . . ?
C3 N1 C2 C1 -172.0(4) . . . . ?
Ni1 N1 C2 C1 13.3(4) . . . . ?
O2 C1 C2 N1 179.4(5) . . . . ?
O1 C1 C2 N1 1.2(6) . . . . ?
O2 C1 C2 C28 -59.7(6) . . . . ?
O1 C1 C2 C28 122.1(5) . . . . ?
O2 C1 C2 C33 57.3(6) . . . . ?
O1 C1 C2 C33 -120.9(5) . . . . ?
C2 N1 C3 C10 -179.8(4) . . . . ?
Ni1 N1 C3 C10 -6.0(7) . . . . ?
C2 N1 C3 C4 -1.3(7) . . . . ?
Ni1 N1 C3 C4 172.6(4) . . . . ?
N1 C3 C4 C5 -90.4(6) . . . . ?
C10 C3 C4 C5 88.3(6) . . . . ?
N1 C3 C4 C9 95.5(6) . . . . ?
C10 C3 C4 C9 -85.8(5) . . . . ?
C9 C4 C5 C6 -2.2(8) . . . . ?
C3 C4 C5 C6 -176.3(5) . . . . ?
C4 C5 C6 C7 2.0(8) . . . . ?
C5 C6 C7 C8 -0.3(8) . . . . ?
C6 C7 C8 C9 -1.1(9) . . . . ?
C7 C8 C9 C4 0.9(8) . . . . ?
C5 C4 C9 C8 0.8(8) . . . . ?
C3 C4 C9 C8 174.8(5) . . . . ?
N1 C3 C10 C15 14.9(7) . . . . ?
C4 C3 C10 C15 -163.9(4) . . . . ?
N1 C3 C10 C11 -165.4(5) . . . . ?
C4 C3 C10 C11 15.9(6) . . . . ?
C15 C10 C11 C12 -3.3(8) . . . . ?
C3 C10 C11 C12 176.9(5) . . . . ?
C10 C11 C12 C13 -0.6(8) . . . . ?
C11 C12 C13 C14 2.3(8) . . . . ?
C12 C13 C14 C15 0.2(7) . . . . ?
C16 N2 C15 C14 -31.0(6) . . . . ?
Ni1 N2 C15 C14 150.0(4) . . . . ?
C16 N2 C15 C10 152.2(4) . . . . ?
Ni1 N2 C15 C10 -26.8(6) . . . . ?
C13 C14 C15 N2 178.9(4) . . . . ?
C13 C14 C15 C10 -4.2(7) . . . . ?
C11 C10 C15 N2 -177.5(4) . . . . ?
C3 C10 C15 N2 2.2(7) . . . . ?
C11 C10 C15 C14 5.6(7) . . . . ?
C3 C10 C15 C14 -174.7(4) . . . . ?
C15 N2 C16 O3 -11.5(7) . . . . ?
Ni1 N2 C16 O3 167.5(4) . . . . ?
C15 N2 C16 C17 170.8(4) . . . . ?
Ni1 N2 C16 C17 -10.1(5) . . . . ?
C20 N3 C17 C16 151.0(4) . . . . ?
C21 N3 C17 C16 -91.2(4) . . . . ?
Ni1 N3 C17 C16 31.2(4) . . . . ?
C20 N3 C17 C18 28.3(4) . . . . ?
C21 N3 C17 C18 146.1(4) . . . . ?
Ni1 N3 C17 C18 -91.5(3) . . . . ?
O3 C16 C17 N3 166.7(4) . . . . ?
N2 C16 C17 N3 -15.5(5) . . . . ?
O3 C16 C17 C18 -75.8(6) . . . . ?
N2 C16 C17 C18 102.1(5) . . . . ?
N3 C17 C18 C19 -2.8(5) . . . . ?
C16 C17 C18 C19 -123.5(4) . . . . ?
C17 C18 C19 C20 -22.9(5) . . . . ?
C17 N3 C20 C19 -43.4(4) . . . . ?
C21 N3 C20 C19 -162.9(3) . . . . ?
Ni1 N3 C20 C19 70.6(4) . . . . ?
C18 C19 C20 N3 40.6(5) . . . . ?
C20 N3 C21 C22 175.3(4) . . . . ?
C17 N3 C21 C22 60.1(5) . . . . ?
Ni1 N3 C21 C22 -57.8(4) . . . . ?
N3 C21 C22 C23 89.3(5) . . . . ?
N3 C21 C22 C27 -93.0(5) . . . . ?
C27 C22 C23 C24 -0.4(7) . . . . ?
C21 C22 C23 C24 177.4(5) . . . . ?
C27 C22 C23 F1 -179.6(4) . . . . ?
C21 C22 C23 F1 -1.8(7) . . . . ?
F1 C23 C24 C25 -178.4(4) . . . . ?
C22 C23 C24 C25 2.4(8) . . . . ?
C23 C24 C25 C26 -2.4(8) . . . . ?
C24 C25 C26 C27 0.6(8) . . . . ?
C25 C26 C27 C22 1.5(7) . . . . ?
C23 C22 C27 C26 -1.6(7) . . . . ?
C21 C22 C27 C26 -179.4(4) . . . . ?
N1 C2 C28 C29 48.9(6) . . . . ?
C33 C2 C28 C29 177.7(4) . . . . ?
C1 C2 C28 C29 -67.8(5) . . . . ?
C2 C28 C29 C30 179.6(4) . . . . ?
C28 C29 C30 C31 65.0(7) . . . . ?
C29 C30 C31 C32 -106.3(7) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.069

_database_code_depnum_ccdc_archive 'CCDC 1020157'
