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

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# 
# This file contains crystal structure data downloaded from the 
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# Crystallographic Data Centre (CCDC).
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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data_20160111a_0m_pl
_database_code_depnum_ccdc_archive 'CCDC 1505512'
_audit_update_record             
;
2016-09-21 deposited with the CCDC.
2017-10-04 downloaded from the CCDC.
;
_audit_creation_date             2016-01-12
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C38 H30 F6 N2 Ni O2'
_chemical_formula_sum            'C38 H30 F6 N2 Ni O2'
_chemical_formula_weight         719.35
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.719(3)
_cell_length_b                   7.351(3)
_cell_length_c                   24.392(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.484(10)
_cell_angle_gamma                90
_cell_volume                     1558.6(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3482
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.610
_cell_measurement_theta_min      3.239
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.698
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.6306
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1105 before and 0.0655 after correction.
The Ratio of minimum to maximum transmission is 0.8463.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             740
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_av_unetI/netI     0.0670
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8579
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        24.795
_diffrn_reflns_theta_max         24.795
_diffrn_reflns_theta_min         3.239
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1984
_reflns_number_total             2618
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         1.162
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.117
_refine_ls_extinction_coef       0.0055(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         2618
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1224
_refine_ls_R_factor_gt           0.0958
_refine_ls_restrained_S_all      1.134
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0227P)²+21.1659P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2224
_refine_ls_wR_factor_ref         0.2299
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F1) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C13(H13), C14(H14), C15(H15), C16(H16)
3.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.5000 0.5000 1.0000 0.0258(5) Uani 1 2 d S T P . .
F1 F 0.1473(10) -0.1980(17) 0.7975(4) 0.155(5) Uani 1 1 d . U . . .
F2 F 0.3433(13) -0.0940(12) 0.7696(3) 0.125(4) Uani 1 1 d . . . . .
F3 F 0.3544(16) -0.3031(13) 0.8221(4) 0.151(5) Uani 1 1 d . . . . .
O2 O 0.4012(6) 0.6555(8) 1.0435(2) 0.0338(14) Uani 1 1 d . . . . .
N1 N 0.3240(8) 0.3437(9) 0.9910(3) 0.0300(16) Uani 1 1 d . . . . .
C1 C 0.2801(13) -0.1481(15) 0.8120(4) 0.051(3) Uani 1 1 d . . . . .
C2 C 0.2927(10) -0.0264(12) 0.8597(4) 0.037(2) Uani 1 1 d . . . . .
C3 C 0.3113(10) -0.0856(12) 0.9118(4) 0.037(2) Uani 1 1 d . . . . .
H3 H 0.3150 -0.2127 0.9189 0.045 Uiso 1 1 calc R . . . .
C4 C 0.3250(10) 0.0348(11) 0.9553(4) 0.036(2) Uani 1 1 d . . . . .
H4 H 0.3411 -0.0099 0.9918 0.043 Uiso 1 1 calc R . . . .
C5 C 0.3157(8) 0.2178(11) 0.9462(3) 0.0257(18) Uani 1 1 d . . . . .
C6 C 0.3017(10) 0.2815(12) 0.8929(3) 0.034(2) Uani 1 1 d . . . . .
H6 H 0.2998 0.4088 0.8862 0.041 Uiso 1 1 calc R . . . .
C7 C 0.2904(11) 0.1629(13) 0.8496(4) 0.039(2) Uani 1 1 d . . . . .
H7 H 0.2811 0.2074 0.8129 0.047 Uiso 1 1 calc R . . . .
C8 C 0.0688(9) 0.2258(13) 1.0090(4) 0.040(2) Uani 1 1 d . . . . .
H8A H 0.0631 0.1907 0.9702 0.059 Uiso 1 1 calc GR . . . .
H8B H -0.0253 0.2908 1.0167 0.059 Uiso 1 1 calc GR . . . .
H8C H 0.0793 0.1165 1.0320 0.059 Uiso 1 1 calc GR . . . .
C9 C 0.2061(9) 0.3479(11) 1.0217(3) 0.0299(19) Uani 1 1 d . . . . .
C10 C 0.1976(8) 0.4646(10) 1.0673(3) 0.0264(18) Uani 1 1 d . . . . .
C11 C 0.2884(9) 0.6150(11) 1.0736(3) 0.0288(19) Uani 1 1 d . . . . .
C12 C 0.2595(9) 0.7574(11) 1.1150(3) 0.0293(19) Uani 1 1 d . . . . .
C13 C 0.3201(10) 0.9260(12) 1.1126(4) 0.038(2) Uani 1 1 d . . . . .
H13 H 0.3850 0.9542 1.0842 0.045 Uiso 1 1 calc R . . . .
C14 C 0.2899(10) 1.0589(12) 1.1505(4) 0.040(2) Uani 1 1 d . . . . .
H14 H 0.3340 1.1765 1.1482 0.048 Uiso 1 1 calc R . . . .
C15 C 0.1954(12) 1.0189(14) 1.1916(4) 0.051(3) Uani 1 1 d . . . . .
H15 H 0.1720 1.1098 1.2174 0.062 Uiso 1 1 calc R . . . .
C16 C 0.1347(12) 0.8454(14) 1.1951(4) 0.049(3) Uani 1 1 d . . . . .
H16 H 0.0708 0.8172 1.2238 0.059 Uiso 1 1 calc R . . . .
C17 C 0.1665(10) 0.7126(12) 1.1572(4) 0.038(2) Uani 1 1 d . . . . .
C18 C 0.1088(12) 0.5240(13) 1.1608(4) 0.049(3) Uani 1 1 d . . . . .
H18A H 0.0176 0.5233 1.1826 0.059 Uiso 1 1 calc R . . . .
H18B H 0.1892 0.4478 1.1804 0.059 Uiso 1 1 calc R . . . .
C19 C 0.0662(10) 0.4436(12) 1.1056(4) 0.040(2) Uani 1 1 d . . . . .
H19A H -0.0273 0.5045 1.0889 0.048 Uiso 1 1 calc R . . . .
H19B H 0.0424 0.3128 1.1098 0.048 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 O2 1.822(5) 3_667 ?
Ni1 O2 1.822(5) . ?
Ni1 N1 1.916(7) . ?
Ni1 N1 1.916(7) 3_667 ?
F1 C1 1.239(12) . ?
F2 C1 1.272(13) . ?
F3 C1 1.324(14) . ?
O2 C11 1.307(9) . ?
N1 C5 1.430(10) . ?
N1 C9 1.318(10) . ?
C1 C2 1.465(13) . ?
C2 C3 1.342(12) . ?
C2 C7 1.413(13) . ?
C3 H3 0.9500 . ?
C3 C4 1.380(12) . ?
C4 H4 0.9500 . ?
C4 C5 1.365(11) . ?
C5 C6 1.378(11) . ?
C6 H6 0.9500 . ?
C6 C7 1.368(12) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8 C9 1.509(11) . ?
C9 C10 1.412(11) . ?
C10 C11 1.361(11) . ?
C10 C19 1.542(11) . ?
C11 C12 1.489(11) . ?
C12 C13 1.351(12) . ?
C12 C17 1.400(12) . ?
C13 H13 0.9500 . ?
C13 C14 1.384(12) . ?
C14 H14 0.9500 . ?
C14 C15 1.378(13) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(14) . ?
C16 H16 0.9500 . ?
C16 C17 1.387(13) . ?
C17 C18 1.479(13) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.491(13) . ?
C19 H19A 0.9900 . ?
C19 H19B 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
O2 Ni1 O2 180.0(3) 3_667 . ?
O2 Ni1 N1 91.8(3) . . ?
O2 Ni1 N1 91.8(3) 3_667 3_667 ?
O2 Ni1 N1 88.2(3) 3_667 . ?
O2 Ni1 N1 88.2(3) . 3_667 ?
N1 Ni1 N1 180.0 . 3_667 ?
C11 O2 Ni1 126.6(5) . . ?
C5 N1 Ni1 117.9(5) . . ?
C9 N1 Ni1 125.0(6) . . ?
C9 N1 C5 117.1(7) . . ?
F1 C1 F2 108.4(11) . . ?
F1 C1 F3 103.4(11) . . ?
F1 C1 C2 114.7(10) . . ?
F2 C1 F3 100.6(11) . . ?
F2 C1 C2 116.3(9) . . ?
F3 C1 C2 111.9(9) . . ?
C3 C2 C1 123.4(9) . . ?
C3 C2 C7 119.0(8) . . ?
C7 C2 C1 117.6(9) . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.1(9) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.4(8) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 N1 120.9(8) . . ?
C4 C5 C6 119.3(8) . . ?
C6 C5 N1 119.8(7) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.5(8) . . ?
C7 C6 H6 119.7 . . ?
C2 C7 H7 120.2 . . ?
C6 C7 C2 119.6(8) . . ?
C6 C7 H7 120.2 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
N1 C9 C8 120.8(8) . . ?
N1 C9 C10 123.6(7) . . ?
C10 C9 C8 115.6(7) . . ?
C9 C10 C19 120.3(7) . . ?
C11 C10 C9 121.1(7) . . ?
C11 C10 C19 117.8(7) . . ?
O2 C11 C10 125.3(8) . . ?
O2 C11 C12 113.3(7) . . ?
C10 C11 C12 121.3(7) . . ?
C13 C12 C11 121.9(8) . . ?
C13 C12 C17 119.9(8) . . ?
C17 C12 C11 118.2(8) . . ?
C12 C13 H13 119.2 . . ?
C12 C13 C14 121.6(9) . . ?
C14 C13 H13 119.2 . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.4(9) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 H15 120.2 . . ?
C14 C15 C16 119.6(9) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.6(9) . . ?
C17 C16 H16 119.7 . . ?
C12 C17 C18 118.9(8) . . ?
C16 C17 C12 118.8(9) . . ?
C16 C17 C18 122.3(9) . . ?
C17 C18 H18A 109.1 . . ?
C17 C18 H18B 109.1 . . ?
C17 C18 C19 112.4(8) . . ?
H18A C18 H18B 107.9 . . ?
C19 C18 H18A 109.1 . . ?
C19 C18 H18B 109.1 . . ?
C10 C19 H19A 109.4 . . ?
C10 C19 H19B 109.4 . . ?
C18 C19 C10 111.3(7) . . ?
C18 C19 H19A 109.4 . . ?
C18 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?

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
Ni1 O2 C11 C10 -18.4(12) . . . . ?
Ni1 O2 C11 C12 165.2(5) . . . . ?
Ni1 N1 C5 C4 112.9(8) . . . . ?
Ni1 N1 C5 C6 -65.7(9) . . . . ?
Ni1 N1 C9 C8 176.5(6) . . . . ?
Ni1 N1 C9 C10 -2.9(12) . . . . ?
F1 C1 C2 C3 88.9(14) . . . . ?
F1 C1 C2 C7 -93.4(13) . . . . ?
F2 C1 C2 C3 -143.2(11) . . . . ?
F2 C1 C2 C7 34.5(15) . . . . ?
F3 C1 C2 C3 -28.4(15) . . . . ?
F3 C1 C2 C7 149.3(11) . . . . ?
O2 C11 C12 C13 14.1(11) . . . . ?
O2 C11 C12 C17 -166.0(7) . . . . ?
N1 Ni1 O2 C11 25.9(7) . . . . ?
N1 Ni1 O2 C11 -154.1(7) 3_667 . . . ?
N1 C5 C6 C7 -178.6(8) . . . . ?
N1 C9 C10 C11 18.8(13) . . . . ?
N1 C9 C10 C19 -171.9(8) . . . . ?
C1 C2 C3 C4 179.0(9) . . . . ?
C1 C2 C7 C6 179.9(9) . . . . ?
C2 C3 C4 C5 1.8(14) . . . . ?
C3 C2 C7 C6 -2.3(14) . . . . ?
C3 C4 C5 N1 177.6(7) . . . . ?
C3 C4 C5 C6 -3.8(13) . . . . ?
C4 C5 C6 C7 2.8(13) . . . . ?
C5 N1 C9 C8 -0.7(12) . . . . ?
C5 N1 C9 C10 180.0(7) . . . . ?
C5 C6 C7 C2 0.2(14) . . . . ?
C7 C2 C3 C4 1.3(14) . . . . ?
C8 C9 C10 C11 -160.5(8) . . . . ?
C8 C9 C10 C19 8.8(11) . . . . ?
C9 N1 C5 C4 -69.7(10) . . . . ?
C9 N1 C5 C6 111.7(9) . . . . ?
C9 C10 C11 O2 -8.3(13) . . . . ?
C9 C10 C11 C12 167.9(7) . . . . ?
C9 C10 C19 C18 157.8(8) . . . . ?
C10 C11 C12 C13 -162.5(8) . . . . ?
C10 C11 C12 C17 17.4(12) . . . . ?
C11 C10 C19 C18 -32.5(11) . . . . ?
C11 C12 C13 C14 178.5(8) . . . . ?
C11 C12 C17 C16 -178.1(8) . . . . ?
C11 C12 C17 C18 3.5(12) . . . . ?
C12 C13 C14 C15 -0.3(15) . . . . ?
C12 C17 C18 C19 -38.1(12) . . . . ?
C13 C12 C17 C16 1.9(13) . . . . ?
C13 C12 C17 C18 -176.5(9) . . . . ?
C13 C14 C15 C16 1.4(15) . . . . ?
C14 C15 C16 C17 -0.9(16) . . . . ?
C15 C16 C17 C12 -0.7(15) . . . . ?
C15 C16 C17 C18 177.6(10) . . . . ?
C16 C17 C18 C19 143.6(9) . . . . ?
C17 C12 C13 C14 -1.4(14) . . . . ?
C17 C18 C19 C10 51.2(11) . . . . ?
C19 C10 C11 O2 -177.9(8) . . . . ?
C19 C10 C11 C12 -1.7(12) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20160108d_0m_pl
_database_code_depnum_ccdc_archive 'CCDC 1505523'
_audit_update_record             
;
2016-09-21 deposited with the CCDC.
2017-10-04 downloaded from the CCDC.
;
_audit_creation_date             2016-01-12
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C38 H36 N2 Ni O4'
_chemical_formula_sum            'C38 H36 N2 Ni O4'
_chemical_formula_weight         643.40
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.6652(13)
_cell_length_b                   14.8520(13)
_cell_length_c                   7.0027(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.988(2)
_cell_angle_gamma                90
_cell_volume                     1519.5(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7299
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      35.002
_cell_measurement_theta_min      3.108
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.684
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.5564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1056 before and 0.0486 after correction.
The Ratio of minimum to maximum transmission is 0.7447.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             676
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9759
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         3.108
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2352
_reflns_number_total             2810
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2810
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0304
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0369P)²+0.4989P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0729
_refine_ls_wR_factor_ref         0.0759
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C16(H16), C17(H17), C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.5000 -1.0000 0.5000 0.02141(11) Uani 1 2 d S T P . .
O1 O 0.86943(9) -0.84706(11) 0.0571(2) 0.0462(4) Uani 1 1 d . . . . .
O2 O 0.38083(8) -0.96390(9) 0.49971(19) 0.0310(3) Uani 1 1 d . . . . .
N1 N 0.52404(9) -0.91468(9) 0.3054(2) 0.0241(3) Uani 1 1 d . . . . .
C1 C 0.89382(17) -0.8801(2) -0.1216(4) 0.0626(7) Uani 1 1 d . . . . .
H1A H 0.8941 -0.9447 -0.1195 0.094 Uiso 1 1 calc GR . . . .
H1B H 0.9537 -0.8585 -0.1440 0.094 Uiso 1 1 calc GR . . . .
H1C H 0.8502 -0.8594 -0.2221 0.094 Uiso 1 1 calc GR . . . .
C2 C 0.78496(12) -0.87035(13) 0.1125(3) 0.0322(4) Uani 1 1 d . . . . .
C3 C 0.72087(13) -0.92023(13) 0.0030(3) 0.0333(4) Uani 1 1 d . . . . .
H3 H 0.7336 -0.9417 -0.1165 0.040 Uiso 1 1 calc R . . . .
C4 C 0.63661(12) -0.93815(12) 0.0735(3) 0.0311(4) Uani 1 1 d . . . . .
H4 H 0.5938 -0.9732 0.0015 0.037 Uiso 1 1 calc R . . . .
C5 C 0.61596(12) -0.90479(11) 0.2479(3) 0.0255(4) Uani 1 1 d . . . . .
C6 C 0.68191(12) -0.85717(12) 0.3594(3) 0.0305(4) Uani 1 1 d . . . . .
H6 H 0.6696 -0.8368 0.4801 0.037 Uiso 1 1 calc R . . . .
C7 C 0.76601(13) -0.83969(13) 0.2924(3) 0.0334(4) Uani 1 1 d . . . . .
H7 H 0.8100 -0.8074 0.3678 0.040 Uiso 1 1 calc R . . . .
C8 C 0.49423(14) -0.78872(15) 0.0801(3) 0.0446(6) Uani 1 1 d . . . . .
H8A H 0.5558 -0.7711 0.1211 0.067 Uiso 1 1 calc GR . . . .
H8B H 0.4546 -0.7374 0.0824 0.067 Uiso 1 1 calc GR . . . .
H8C H 0.4920 -0.8122 -0.0480 0.067 Uiso 1 1 calc GR . . . .
C9 C 0.46318(12) -0.86036(12) 0.2132(3) 0.0267(4) Uani 1 1 d . . . . .
C10 C 0.36777(12) -0.86323(12) 0.2354(3) 0.0260(4) Uani 1 1 d . . . . .
C11 C 0.30363(13) -0.80399(14) 0.1095(3) 0.0374(5) Uani 1 1 d . . . . .
H11A H 0.3020 -0.7445 0.1662 0.045 Uiso 1 1 calc R . . . .
H11B H 0.3271 -0.7979 -0.0151 0.045 Uiso 1 1 calc R . . . .
C12 C 0.20737(14) -0.84130(15) 0.0837(3) 0.0419(5) Uani 1 1 d . . . . .
H12A H 0.1669 -0.7962 0.0223 0.050 Uiso 1 1 calc R . . . .
H12B H 0.2064 -0.8934 0.0000 0.050 Uiso 1 1 calc R . . . .
C13 C 0.17297(12) -0.86780(12) 0.2697(3) 0.0308(4) Uani 1 1 d . . . . .
C14 C 0.23456(11) -0.90558(11) 0.4115(3) 0.0254(4) Uani 1 1 d . . . . .
C15 C 0.33318(11) -0.91269(11) 0.3786(3) 0.0237(4) Uani 1 1 d . . . . .
C16 C 0.20303(12) -0.93484(13) 0.5821(3) 0.0325(4) Uani 1 1 d . . . . .
H16 H 0.2439 -0.9597 0.6767 0.039 Uiso 1 1 calc R . . . .
C17 C 0.11148(14) -0.92741(15) 0.6129(3) 0.0434(5) Uani 1 1 d . . . . .
H17 H 0.0908 -0.9480 0.7269 0.052 Uiso 1 1 calc R . . . .
C18 C 0.05090(13) -0.88943(16) 0.4740(3) 0.0463(6) Uani 1 1 d . . . . .
H18 H -0.0106 -0.8839 0.4948 0.056 Uiso 1 1 calc R . . . .
C19 C 0.08149(13) -0.85985(15) 0.3051(3) 0.0424(5) Uani 1 1 d . . . . .
H19 H 0.0402 -0.8340 0.2126 0.051 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 O2 1.8279(11) . ?
Ni1 O2 1.8279(11) 3_636 ?
Ni1 N1 1.9158(14) 3_636 ?
Ni1 N1 1.9158(14) . ?
O1 C1 1.418(3) . ?
O1 C2 1.374(2) . ?
O2 C15 1.297(2) . ?
N1 C5 1.447(2) . ?
N1 C9 1.328(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.376(3) . ?
C2 C7 1.391(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.396(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.376(3) . ?
C5 C6 1.383(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.382(2) . ?
C7 H7 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C8 C9 1.511(2) . ?
C9 C10 1.422(2) . ?
C10 C11 1.514(2) . ?
C10 C15 1.375(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.513(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.490(3) . ?
C13 C14 1.400(3) . ?
C13 C19 1.390(3) . ?
C14 C15 1.488(2) . ?
C14 C16 1.388(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.382(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.380(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.373(3) . ?
C19 H19 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Ni1 O2 180.0 . 3_636 ?
O2 Ni1 N1 87.69(6) . 3_636 ?
O2 Ni1 N1 92.31(6) 3_636 3_636 ?
O2 Ni1 N1 92.31(6) . . ?
O2 Ni1 N1 87.69(6) 3_636 . ?
N1 Ni1 N1 180.0 3_636 . ?
C2 O1 C1 117.70(18) . . ?
C15 O2 Ni1 129.29(11) . . ?
C5 N1 Ni1 119.89(11) . . ?
C9 N1 Ni1 126.16(12) . . ?
C9 N1 C5 113.95(14) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 124.54(18) . . ?
O1 C2 C7 115.44(18) . . ?
C3 C2 C7 120.02(16) . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.24(18) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.01(18) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 N1 119.51(17) . . ?
C4 C5 C6 119.21(16) . . ?
C6 C5 N1 121.14(16) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.37(17) . . ?
C7 C6 H6 119.8 . . ?
C2 C7 H7 120.0 . . ?
C6 C7 C2 120.04(18) . . ?
C6 C7 H7 120.0 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
N1 C9 C8 120.12(16) . . ?
N1 C9 C10 123.70(16) . . ?
C10 C9 C8 116.15(16) . . ?
C9 C10 C11 119.11(16) . . ?
C15 C10 C9 121.64(16) . . ?
C15 C10 C11 119.03(15) . . ?
C10 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 C10 112.51(16) . . ?
C12 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C11 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C13 C12 C11 112.05(17) . . ?
C13 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C14 C13 C12 118.64(16) . . ?
C19 C13 C12 122.59(18) . . ?
C19 C13 C14 118.72(18) . . ?
C13 C14 C15 119.61(16) . . ?
C16 C14 C13 119.56(16) . . ?
C16 C14 C15 120.82(17) . . ?
O2 C15 C10 125.32(15) . . ?
O2 C15 C14 114.56(15) . . ?
C10 C15 C14 120.02(16) . . ?
C14 C16 H16 119.7 . . ?
C17 C16 C14 120.66(19) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.8(2) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 119.96(19) . . ?
C19 C18 H18 120.0 . . ?
C13 C19 H19 119.4 . . ?
C18 C19 C13 121.3(2) . . ?
C18 C19 H19 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ni1 O2 C15 C10 -10.1(3) . . . . ?
Ni1 O2 C15 C14 173.58(12) . . . . ?
Ni1 N1 C5 C4 106.63(17) . . . . ?
Ni1 N1 C5 C6 -77.70(19) . . . . ?
Ni1 N1 C9 C8 172.66(15) . . . . ?
Ni1 N1 C9 C10 -5.5(3) . . . . ?
O1 C2 C3 C4 -178.79(18) . . . . ?
O1 C2 C7 C6 178.11(17) . . . . ?
N1 Ni1 O2 C15 -167.95(16) 3_636 . . . ?
N1 Ni1 O2 C15 12.05(16) . . . . ?
N1 C5 C6 C7 -172.65(16) . . . . ?
N1 C9 C10 C11 -174.39(17) . . . . ?
N1 C9 C10 C15 11.1(3) . . . . ?
C1 O1 C2 C3 -2.9(3) . . . . ?
C1 O1 C2 C7 177.2(2) . . . . ?
C2 C3 C4 C5 1.7(3) . . . . ?
C3 C2 C7 C6 -1.8(3) . . . . ?
C3 C4 C5 N1 172.00(17) . . . . ?
C3 C4 C5 C6 -3.7(3) . . . . ?
C4 C5 C6 C7 3.0(3) . . . . ?
C5 N1 C9 C8 -6.9(2) . . . . ?
C5 N1 C9 C10 174.91(17) . . . . ?
C5 C6 C7 C2 -0.3(3) . . . . ?
C7 C2 C3 C4 1.1(3) . . . . ?
C8 C9 C10 C11 7.3(3) . . . . ?
C8 C9 C10 C15 -167.18(18) . . . . ?
C9 N1 C5 C4 -73.8(2) . . . . ?
C9 N1 C5 C6 101.9(2) . . . . ?
C9 C10 C11 C12 154.53(18) . . . . ?
C9 C10 C15 O2 -3.4(3) . . . . ?
C9 C10 C15 C14 172.82(16) . . . . ?
C10 C11 C12 C13 48.6(2) . . . . ?
C11 C10 C15 O2 -177.89(18) . . . . ?
C11 C10 C15 C14 -1.7(3) . . . . ?
C11 C12 C13 C14 -36.3(3) . . . . ?
C11 C12 C13 C19 146.37(19) . . . . ?
C12 C13 C14 C15 4.0(3) . . . . ?
C12 C13 C14 C16 -176.81(18) . . . . ?
C12 C13 C19 C18 176.4(2) . . . . ?
C13 C14 C15 O2 -167.09(16) . . . . ?
C13 C14 C15 C10 16.3(3) . . . . ?
C13 C14 C16 C17 0.3(3) . . . . ?
C14 C13 C19 C18 -1.0(3) . . . . ?
C14 C16 C17 C18 -0.9(3) . . . . ?
C15 C10 C11 C12 -30.8(3) . . . . ?
C15 C14 C16 C17 179.44(18) . . . . ?
C16 C14 C15 O2 13.8(2) . . . . ?
C16 C14 C15 C10 -162.80(17) . . . . ?
C16 C17 C18 C19 0.6(4) . . . . ?
C17 C18 C19 C13 0.4(4) . . . . ?
C19 C13 C14 C15 -178.52(17) . . . . ?
C19 C13 C14 C16 0.6(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1505524'
_audit_update_record             
;
2016-09-21 deposited with the CCDC.
2017-10-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H30 F2 N2 Ni O2'
_chemical_formula_weight         619.33

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   p21/n

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

_cell_length_a                   8.916(3)
_cell_length_b                   7.111(3)
_cell_length_c                   21.905(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.538(9)
_cell_angle_gamma                90.00
_cell_volume                     1386.2(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             644
_exptl_absorpt_coefficient_mu    0.752
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8415
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.42
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2632
_reflns_number_gt                2235
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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+4.4658P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2632
_refine_ls_number_parameters     197
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1003
_refine_ls_wR_factor_gt          0.0972
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_restrained_S_all      0.950
_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
C1 C 0.1921(4) 1.0491(6) -0.14891(17) 0.0432(10) Uani 1 1 d . . .
C2 C 0.1813(4) 1.1117(5) -0.09084(17) 0.0406(9) Uani 1 1 d . . .
H2 H 0.1819 1.2397 -0.0822 0.049 Uiso 1 1 calc R . .
C3 C 0.1692(4) 0.9797(5) -0.04456(16) 0.0341(7) Uani 1 1 d . . .
H3 H 0.1597 1.0196 -0.0045 0.041 Uiso 1 1 calc R . .
C4 C 0.1711(3) 0.7887(5) -0.05769(14) 0.0271(7) Uani 1 1 d . . .
C5 C 0.1750(4) 0.7308(5) -0.11796(15) 0.0337(8) Uani 1 1 d . . .
H5 H 0.1700 0.6034 -0.1274 0.040 Uiso 1 1 calc R . .
C6 C 0.1863(4) 0.8620(6) -0.16432(16) 0.0433(9) Uani 1 1 d . . .
H6 H 0.1899 0.8241 -0.2048 0.052 Uiso 1 1 calc R . .
C7 C 0.4316(4) 0.7699(5) 0.01365(17) 0.0381(8) Uani 1 1 d . . .
H7A H 0.4247 0.8072 -0.0286 0.057 Uiso 1 1 calc R . .
H7B H 0.5236 0.7024 0.0224 0.057 Uiso 1 1 calc R . .
H7C H 0.4300 0.8796 0.0391 0.057 Uiso 1 1 calc R . .
C8 C 0.2993(3) 0.6442(4) 0.02624(14) 0.0265(7) Uani 1 1 d . . .
C9 C 0.3237(3) 0.5194(5) 0.07635(14) 0.0276(7) Uani 1 1 d . . .
C10 C 0.4677(4) 0.5335(5) 0.11676(16) 0.0358(8) Uani 1 1 d . . .
H10A H 0.5484 0.4736 0.0962 0.043 Uiso 1 1 calc R . .
H10B H 0.4937 0.6650 0.1225 0.043 Uiso 1 1 calc R . .
C11 C 0.4553(4) 0.4428(5) 0.17866(16) 0.0390(9) Uani 1 1 d . . .
H11A H 0.5547 0.4329 0.1990 0.047 Uiso 1 1 calc R . .
H11B H 0.3952 0.5226 0.2035 0.047 Uiso 1 1 calc R . .
C12 C 0.3856(4) 0.2512(5) 0.17419(15) 0.0303(7) Uani 1 1 d . . .
C13 C 0.4254(4) 0.1085(5) 0.21560(16) 0.0382(8) Uani 1 1 d . . .
H13 H 0.5032 0.1281 0.2452 0.046 Uiso 1 1 calc R . .
C14 C 0.3505(4) -0.0621(5) 0.21326(16) 0.0399(9) Uani 1 1 d . . .
H14 H 0.3783 -0.1566 0.2410 0.048 Uiso 1 1 calc R . .
C15 C 0.2352(4) -0.0916(5) 0.16992(17) 0.0395(9) Uani 1 1 d . . .
H15 H 0.1843 -0.2058 0.1685 0.047 Uiso 1 1 calc R . .
C16 C 0.1947(4) 0.0486(5) 0.12843(15) 0.0330(8) Uani 1 1 d . . .
H16 H 0.1160 0.0282 0.0993 0.040 Uiso 1 1 calc R . .
C17 C 0.2704(3) 0.2201(4) 0.12973(14) 0.0268(7) Uani 1 1 d . . .
C18 C 0.2280(3) 0.3701(5) 0.08433(14) 0.0254(7) Uani 1 1 d . . .
F1 F 0.2083(3) 1.1784(4) -0.19413(11) 0.0712(8) Uani 1 1 d . . .
N1 N 0.1743(3) 0.6523(4) -0.00888(12) 0.0258(6) Uani 1 1 d . . .
Ni1 Ni 0.0000 0.5000 0.0000 0.02339(15) Uani 1 2 d S . .
O1 O 0.1036(2) 0.3401(3) 0.05275(10) 0.0315(5) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.357(5) . ?
C1 F1 1.366(4) . ?
C1 C6 1.373(6) . ?
C2 C3 1.391(5) . ?
C3 C4 1.389(5) . ?
C4 C5 1.385(5) . ?
C4 N1 1.443(4) . ?
C5 C6 1.387(5) . ?
C7 C8 1.518(4) . ?
C8 N1 1.316(4) . ?
C8 C9 1.418(4) . ?
C9 C18 1.380(4) . ?
C9 C10 1.517(4) . ?
C10 C11 1.512(5) . ?
C11 C12 1.498(5) . ?
C12 C13 1.392(5) . ?
C12 C17 1.389(4) . ?
C13 C14 1.385(5) . ?
C14 C15 1.372(5) . ?
C15 C16 1.382(5) . ?
C16 C17 1.394(4) . ?
C17 C18 1.491(4) . ?
C18 O1 1.288(4) . ?
N1 Ni1 1.914(2) . ?
Ni1 O1 1.830(2) 3_565 ?
Ni1 O1 1.830(2) . ?
Ni1 N1 1.914(2) 3_565 ?

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
C2 C1 F1 118.4(4) . . ?
C2 C1 C6 123.0(3) . . ?
F1 C1 C6 118.6(4) . . ?
C1 C2 C3 118.4(4) . . ?
C2 C3 C4 120.4(3) . . ?
C5 C4 C3 119.3(3) . . ?
C5 C4 N1 120.4(3) . . ?
C3 C4 N1 120.3(3) . . ?
C4 C5 C6 120.3(3) . . ?
C1 C6 C5 118.4(3) . . ?
N1 C8 C9 124.3(3) . . ?
N1 C8 C7 120.5(3) . . ?
C9 C8 C7 115.2(3) . . ?
C18 C9 C8 120.9(3) . . ?
C18 C9 C10 119.0(3) . . ?
C8 C9 C10 119.6(3) . . ?
C11 C10 C9 112.9(3) . . ?
C12 C11 C10 112.5(3) . . ?
C13 C12 C17 119.2(3) . . ?
C13 C12 C11 122.2(3) . . ?
C17 C12 C11 118.5(3) . . ?
C14 C13 C12 120.8(3) . . ?
C15 C14 C13 119.9(3) . . ?
C14 C15 C16 120.0(3) . . ?
C15 C16 C17 120.7(3) . . ?
C16 C17 C12 119.4(3) . . ?
C16 C17 C18 120.6(3) . . ?
C12 C17 C18 120.0(3) . . ?
O1 C18 C9 125.3(3) . . ?
O1 C18 C17 114.4(3) . . ?
C9 C18 C17 120.1(3) . . ?
C8 N1 C4 116.1(2) . . ?
C8 N1 Ni1 125.5(2) . . ?
C4 N1 Ni1 118.47(19) . . ?
O1 Ni1 O1 180.00(11) 3_565 . ?
O1 Ni1 N1 88.03(10) 3_565 . ?
O1 Ni1 N1 91.97(10) . . ?
O1 Ni1 N1 91.97(10) 3_565 3_565 ?
O1 Ni1 N1 88.03(10) . 3_565 ?
N1 Ni1 N1 180.00(15) . 3_565 ?
C18 O1 Ni1 128.3(2) . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.061
