# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_ga_cr6
_database_code_depnum_ccdc_archive 'CCDC 1427461'
_audit_update_record             
;
2015-09-25 deposited with the CCDC.
2015-11-09 downloaded from the CCDC.
;
_audit_creation_date             2015-09-25

_audit_block_code                ga_cr6
_audit_block_refno               1041
_audit_block_usercomment         CR100lr_r


_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C18 H26 N3 Ni O2'
_chemical_formula_sum            'C18 H26 N3 Ni O2'
_chemical_formula_weight         375.13
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_h-m   'P 21 21 21'
_symmetry_int_tables_number      19

_chemical_absolute_configuration ad
_chemical_melting_point          ?
_exptl_crystal_description       block
_exptl_crystal_colour            red
_diffrn_ambient_temperature      100(1)
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'

_space_group_name_Hall           'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.790(3)
_cell_length_b                   10.095(5)
_cell_length_c                   29.897(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1747.5(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8131
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.19
_cell_measurement_theta_min      2.43
_shelx_estimated_absorpt_T_max   0.896
_shelx_estimated_absorpt_T_min   0.806
_exptl_absorpt_coefficient_mu    1.125
_exptl_absorpt_correction_T_max  0.8623
_exptl_absorpt_correction_T_min  0.7985

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements (Blessing 1995)
SADABS (see _computing_data_reduction)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             796
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            45811
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.572
_diffrn_reflns_theta_min         2.129
_diffrn_detector_area_resol_mean 8.19
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker AXS Smart 1000'
_diffrn_measurement_method       'φ- and ω-scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-Ray tube (Mo)'
_diffrn_source_type              'fine focus tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.945
_reflns_number_gt                5551
_reflns_number_total             6139
_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 (see _computing_data_reduction). Includes estimated systematic errors
 of the unit cell constants from Monte Carlo simulations.
;
_computing_data_collection       'SMART-5.631 (Bruker AXS, 2003)'
_computing_data_reduction        
'SAINT V8.34A (Bruker AXS, 1997-2013),SADABS-2014_5 (Sheldrick and Bruker AXS, 1997-2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  
'encif (Wadepohl, 2009-14); encifer 1.5 (CCDC, 2014)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_shelxl_version_number           2014/7
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007-2009)'
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 
;
 Flack x determined using 2168 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         6139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0313
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0345P)²+0.0654P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0657
_refine_ls_wR_factor_ref         0.0682
_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 Idealised Me refined as rotating group with stretchable bonds:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
Ni Ni 0.01776(4) 0.31482(2) 0.89341(2) 0.01172(6) Uani 1 1 d . . . . .
O1 O 0.4319(3) 0.63920(15) 0.88552(5) 0.0203(3) Uani 1 1 d . . . . .
O2 O -0.4526(3) 0.03695(15) 0.93055(5) 0.0202(3) Uani 1 1 d . . . . .
N1 N 0.2386(3) 0.44637(17) 0.87865(5) 0.0127(3) Uani 1 1 d . . . . .
N2 N -0.1389(3) 0.42013(17) 0.93794(5) 0.0137(3) Uani 1 1 d . . . . .
N3 N -0.1689(3) 0.16248(16) 0.90009(5) 0.0133(3) Uani 1 1 d . . . . .
C1 C 0.4278(4) 0.4360(2) 0.84569(7) 0.0146(4) Uani 1 1 d . . . . .
H1 H 0.518(4) 0.365(2) 0.8534(8) 0.018 Uiso 1 1 d R . . . .
C2 C 0.5636(4) 0.5651(2) 0.85297(7) 0.0178(4) Uani 1 1 d . . . . .
H2A H 0.574(4) 0.619(3) 0.8255(9) 0.021 Uiso 1 1 d R . . . .
H2B H 0.714(5) 0.551(3) 0.8659(9) 0.021 Uiso 1 1 d R . . . .
C3 C 0.2515(3) 0.56130(19) 0.89850(7) 0.0143(4) Uani 1 1 d . . . . .
C4 C 0.1011(4) 0.6139(2) 0.93142(7) 0.0165(4) Uani 1 1 d . . . . .
H4 H 0.140(5) 0.695(3) 0.9419(8) 0.020 Uiso 1 1 d R . . . .
C5 C -0.0806(4) 0.5466(2) 0.94965(6) 0.0157(4) Uani 1 1 d . . . . .
C6 C -0.2443(4) 0.6008(2) 0.98453(7) 0.0207(5) Uani 1 1 d . . . . .
H6A H -0.335(5) 0.676(3) 0.9729(9) 0.025 Uiso 1 1 d R . . . .
H6B H -0.157(5) 0.630(3) 1.0096(9) 0.025 Uiso 1 1 d R . . . .
C7 C -0.4018(4) 0.4834(2) 0.99492(7) 0.0205(4) Uani 1 1 d . . . . .
H7A H -0.565(5) 0.507(3) 0.9904(9) 0.025 Uiso 1 1 d R . . . .
H7B H -0.387(5) 0.452(3) 1.0251(9) 0.025 Uiso 1 1 d R . . . .
C8 C -0.3236(4) 0.3783(2) 0.96224(7) 0.0152(4) Uani 1 1 d . . . . .
C9 C -0.4187(4) 0.2548(2) 0.95868(7) 0.0180(4) Uani 1 1 d . . . . .
H9 H -0.540(5) 0.234(3) 0.9759(8) 0.022 Uiso 1 1 d R . . . .
C10 C -0.3381(4) 0.1559(2) 0.92916(7) 0.0158(4) Uani 1 1 d . . . . .
C11 C -0.3191(4) -0.0530(2) 0.90338(8) 0.0199(4) Uani 1 1 d . . . . .
H11A H -0.425(5) -0.106(3) 0.8859(8) 0.024 Uiso 1 1 d R . . . .
H11B H -0.214(5) -0.108(3) 0.9229(9) 0.024 Uiso 1 1 d R . . . .
C12 C -0.1694(4) 0.0370(2) 0.87425(7) 0.0148(4) Uani 1 1 d . . . . .
H12 H -0.237(4) 0.051(3) 0.8457(9) 0.018 Uiso 1 1 d R . . . .
C13 C 0.0685(4) -0.0197(2) 0.86440(7) 0.0143(4) Uani 1 1 d . . . . .
H13 H 0.154(4) -0.036(3) 0.8928(8) 0.017 Uiso 1 1 d R . . . .
C14 C 0.2161(4) 0.0777(2) 0.83796(7) 0.0180(4) Uani 1 1 d . . . . .
H14A H 0.364(3) 0.0339(8) 0.8290(5) 0.027 Uiso 1 1 calc GR . . . .
H14B H 0.251(2) 0.1567(14) 0.8570(3) 0.027 Uiso 1 1 calc GR . . . .
H14C H 0.1304(17) 0.1066(13) 0.8106(5) 0.027 Uiso 1 1 calc GR . . . .
C15 C 0.0426(4) -0.1504(2) 0.83872(7) 0.0206(4) Uani 1 1 d . . . . .
H15A H -0.038(3) -0.1346(4) 0.8113(5) 0.031 Uiso 1 1 calc GR . . . .
H15B H -0.043(3) -0.2122(11) 0.8565(4) 0.031 Uiso 1 1 calc GR . . . .
H15C H 0.192(2) -0.1859(10) 0.8324(5) 0.031 Uiso 1 1 calc GR . . . .
C16 C 0.3345(4) 0.4166(2) 0.79808(7) 0.0177(4) Uani 1 1 d . . . . .
H16 H 0.227(5) 0.345(3) 0.7983(8) 0.021 Uiso 1 1 d R . . . .
C17 C 0.5290(5) 0.3859(3) 0.76579(8) 0.0336(6) Uani 1 1 d . . . . .
H17A H 0.4665(12) 0.3639(19) 0.7375(5) 0.050 Uiso 1 1 calc GR . . . .
H17B H 0.616(3) 0.3137(18) 0.7768(4) 0.050 Uiso 1 1 calc GR . . . .
H17C H 0.626(3) 0.4610(14) 0.7629(5) 0.050 Uiso 1 1 calc GR . . . .
C18 C 0.1861(4) 0.5311(2) 0.78203(7) 0.0237(5) Uani 1 1 d . . . . .
H18A H 0.2809(17) 0.6106(14) 0.7794(5) 0.036 Uiso 1 1 calc GR . . . .
H18B H 0.062(3) 0.5468(12) 0.8035(5) 0.036 Uiso 1 1 calc GR . . . .
H18C H 0.120(3) 0.5094(8) 0.7529(5) 0.036 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni N1 1.8955(19) . ?
Ni N2 1.9301(18) . ?
Ni N3 1.8903(18) . ?
O1 C2 1.445(3) . ?
O1 C3 1.364(2) . ?
O2 C10 1.372(3) . ?
O2 C11 1.443(3) . ?
N1 C1 1.478(3) . ?
N1 C3 1.305(3) . ?
N2 C5 1.366(3) . ?
N2 C8 1.360(3) . ?
N3 C10 1.311(3) . ?
N3 C12 1.484(3) . ?
C1 H1 0.92(2) . ?
C1 C2 1.538(3) . ?
C1 C16 1.535(3) . ?
C2 H2A 0.99(3) . ?
C2 H2B 0.96(3) . ?
C3 C4 1.417(3) . ?
C4 H4 0.90(3) . ?
C4 C5 1.366(3) . ?
C5 C6 1.512(3) . ?
C6 H6A 0.98(3) . ?
C6 H6B 0.95(3) . ?
C6 C7 1.527(4) . ?
C7 H7A 0.98(3) . ?
C7 H7B 0.96(3) . ?
C7 C8 1.512(3) . ?
C8 C9 1.367(3) . ?
C9 H9 0.90(3) . ?
C9 C10 1.411(3) . ?
C11 H11A 0.97(3) . ?
C11 H11B 1.01(3) . ?
C11 C12 1.528(3) . ?
C12 H12 0.95(3) . ?
C12 C13 1.520(3) . ?
C13 H13 0.99(3) . ?
C13 C14 1.524(3) . ?
C13 C15 1.534(3) . ?
C14 H14A 1.000(15) . ?
C14 H14B 1.000(15) . ?
C14 H14C 1.000(15) . ?
C15 H15A 0.957(15) . ?
C15 H15B 0.957(15) . ?
C15 H15C 0.957(15) . ?
C16 H16 0.96(3) . ?
C16 C17 1.515(3) . ?
C16 C18 1.518(3) . ?
C17 H17A 0.946(16) . ?
C17 H17B 0.946(16) . ?
C17 H17C 0.946(17) . ?
C18 H18A 0.976(16) . ?
C18 H18B 0.976(16) . ?
C18 H18C 0.976(16) . ?

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 Ni N2 95.26(8) . . ?
N3 Ni N1 168.60(7) . . ?
N3 Ni N2 96.12(8) . . ?
C3 O1 C2 107.31(16) . . ?
C10 O2 C11 105.97(16) . . ?
C1 N1 Ni 127.28(13) . . ?
C3 N1 Ni 123.74(15) . . ?
C3 N1 C1 108.90(17) . . ?
C5 N2 Ni 125.12(14) . . ?
C8 N2 Ni 124.54(15) . . ?
C8 N2 C5 110.34(17) . . ?
C10 N3 Ni 122.57(14) . . ?
C10 N3 C12 107.49(17) . . ?
C12 N3 Ni 129.84(13) . . ?
N1 C1 H1 108.2(15) . . ?
N1 C1 C2 102.97(16) . . ?
N1 C1 C16 111.50(17) . . ?
C2 C1 H1 109.6(16) . . ?
C16 C1 H1 109.5(15) . . ?
C16 C1 C2 114.78(17) . . ?
O1 C2 C1 105.32(16) . . ?
O1 C2 H2A 107.7(15) . . ?
O1 C2 H2B 106.4(16) . . ?
C1 C2 H2A 112.5(16) . . ?
C1 C2 H2B 113.1(16) . . ?
H2A C2 H2B 111(2) . . ?
O1 C3 C4 116.87(18) . . ?
N1 C3 O1 115.27(18) . . ?
N1 C3 C4 127.86(19) . . ?
C3 C4 H4 115.3(17) . . ?
C5 C4 C3 124.32(19) . . ?
C5 C4 H4 120.2(17) . . ?
N2 C5 C6 111.08(19) . . ?
C4 C5 N2 123.58(19) . . ?
C4 C5 C6 125.34(19) . . ?
C5 C6 H6A 111.6(15) . . ?
C5 C6 H6B 108.8(16) . . ?
C5 C6 C7 103.56(18) . . ?
H6A C6 H6B 109(2) . . ?
C7 C6 H6A 110.5(17) . . ?
C7 C6 H6B 113.3(16) . . ?
C6 C7 H7A 111.2(17) . . ?
C6 C7 H7B 113.4(17) . . ?
H7A C7 H7B 107(2) . . ?
C8 C7 C6 103.54(18) . . ?
C8 C7 H7A 111.4(17) . . ?
C8 C7 H7B 110.2(17) . . ?
N2 C8 C7 111.28(19) . . ?
N2 C8 C9 123.92(19) . . ?
C9 C8 C7 124.7(2) . . ?
C8 C9 H9 119.2(17) . . ?
C8 C9 C10 124.1(2) . . ?
C10 C9 H9 116.7(17) . . ?
O2 C10 C9 116.11(18) . . ?
N3 C10 O2 115.16(18) . . ?
N3 C10 C9 128.7(2) . . ?
O2 C11 H11A 108.4(16) . . ?
O2 C11 H11B 110.0(15) . . ?
O2 C11 C12 104.50(17) . . ?
H11A C11 H11B 113(2) . . ?
C12 C11 H11A 112.3(16) . . ?
C12 C11 H11B 108.4(16) . . ?
N3 C12 C11 102.24(17) . . ?
N3 C12 H12 109.8(16) . . ?
N3 C12 C13 114.88(17) . . ?
C11 C12 H12 111.7(16) . . ?
C13 C12 C11 113.61(17) . . ?
C13 C12 H12 104.8(16) . . ?
C12 C13 H13 110.3(14) . . ?
C12 C13 C14 111.44(17) . . ?
C12 C13 C15 109.39(17) . . ?
C14 C13 H13 105.7(15) . . ?
C14 C13 C15 110.52(18) . . ?
C15 C13 H13 109.5(15) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 C16 H16 108.7(15) . . ?
C17 C16 C1 110.8(2) . . ?
C17 C16 H16 109.6(15) . . ?
C17 C16 C18 112.0(2) . . ?
C18 C16 C1 113.28(18) . . ?
C18 C16 H16 102.0(16) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
Ni N1 C1 C2 -173.14(13) . . . . ?
Ni N1 C1 C16 63.3(2) . . . . ?
Ni N1 C3 O1 175.52(13) . . . . ?
Ni N1 C3 C4 -4.7(3) . . . . ?
Ni N2 C5 C4 -1.1(3) . . . . ?
Ni N2 C5 C6 178.20(14) . . . . ?
Ni N2 C8 C7 178.70(14) . . . . ?
Ni N2 C8 C9 1.3(3) . . . . ?
Ni N3 C10 O2 -178.32(13) . . . . ?
Ni N3 C10 C9 2.4(3) . . . . ?
Ni N3 C12 C11 167.43(14) . . . . ?
Ni N3 C12 C13 43.9(2) . . . . ?
O1 C3 C4 C5 -176.65(19) . . . . ?
O2 C11 C12 N3 21.1(2) . . . . ?
O2 C11 C12 C13 145.49(17) . . . . ?
N1 Ni N3 C10 174.8(3) . . . . ?
N1 Ni N3 C12 -9.2(5) . . . . ?
N1 C1 C2 O1 -4.6(2) . . . . ?
N1 C1 C16 C17 -171.64(19) . . . . ?
N1 C1 C16 C18 61.5(2) . . . . ?
N1 C3 C4 C5 3.6(3) . . . . ?
N2 Ni N1 C1 179.17(16) . . . . ?
N2 Ni N1 C3 2.57(17) . . . . ?
N2 Ni N3 C10 -1.17(16) . . . . ?
N2 Ni N3 C12 174.78(17) . . . . ?
N2 C5 C6 C7 4.1(2) . . . . ?
N2 C8 C9 C10 -0.5(3) . . . . ?
N3 Ni N1 C1 3.2(5) . . . . ?
N3 Ni N1 C3 -173.4(3) . . . . ?
N3 C12 C13 C14 -58.9(2) . . . . ?
N3 C12 C13 C15 178.57(16) . . . . ?
C1 N1 C3 O1 -1.6(2) . . . . ?
C1 N1 C3 C4 178.14(19) . . . . ?
C2 O1 C3 N1 -1.6(2) . . . . ?
C2 O1 C3 C4 178.61(17) . . . . ?
C2 C1 C16 C17 71.8(2) . . . . ?
C2 C1 C16 C18 -55.1(3) . . . . ?
C3 O1 C2 C1 3.9(2) . . . . ?
C3 N1 C1 C2 3.9(2) . . . . ?
C3 N1 C1 C16 -119.71(18) . . . . ?
C3 C4 C5 N2 -0.3(3) . . . . ?
C3 C4 C5 C6 -179.55(19) . . . . ?
C4 C5 C6 C7 -176.6(2) . . . . ?
C5 N2 C8 C7 -1.2(2) . . . . ?
C5 N2 C8 C9 -178.54(19) . . . . ?
C5 C6 C7 C8 -4.4(2) . . . . ?
C6 C7 C8 N2 3.6(2) . . . . ?
C6 C7 C8 C9 -179.0(2) . . . . ?
C7 C8 C9 C10 -177.5(2) . . . . ?
C8 N2 C5 C4 178.74(19) . . . . ?
C8 N2 C5 C6 -1.9(2) . . . . ?
C8 C9 C10 O2 179.10(19) . . . . ?
C8 C9 C10 N3 -1.6(4) . . . . ?
C10 O2 C11 C12 -18.9(2) . . . . ?
C10 N3 C12 C11 -16.1(2) . . . . ?
C10 N3 C12 C13 -139.67(18) . . . . ?
C11 O2 C10 N3 9.5(2) . . . . ?
C11 O2 C10 C9 -171.12(18) . . . . ?
C11 C12 C13 C14 -176.16(18) . . . . ?
C11 C12 C13 C15 61.3(2) . . . . ?
C12 N3 C10 O2 4.9(2) . . . . ?
C12 N3 C10 C9 -174.4(2) . . . . ?
C16 C1 C2 O1 116.74(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

_diffrn_ambient_environment      'perfluoro polyether oil / N~2~'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_specimen_support 'polyimid foil'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            CCD-PXL-KAF2
####################################################################### 
# 
# 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_ga_cr31
_database_code_depnum_ccdc_archive 'CCDC 1427462'
_audit_update_record             
;
2015-09-25 deposited with the CCDC.
2015-11-09 downloaded from the CCDC.
;
_audit_creation_date             2015-09-24

_audit_block_code                ga_cr31
_audit_block_refno               1576
_audit_block_usercomment         cr606


_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C24 H23 F2 N3 Ni O2'
_chemical_formula_sum            'C24 H23 F2 N3 Ni O2'
_chemical_formula_weight         482.16
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_h-m   'P 21 21 21'
_symmetry_int_tables_number      19

_chemical_absolute_configuration ad
_chemical_melting_point          ?
_exptl_crystal_description       plate
_exptl_crystal_colour            red
_diffrn_ambient_temperature      100(1)
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'

_space_group_name_Hall           'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   10.148(5)
_cell_length_b                   11.913(5)
_cell_length_c                   17.409(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2104.6(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8050
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.11
_cell_measurement_theta_min      2.32
_shelx_estimated_absorpt_T_max   0.953
_shelx_estimated_absorpt_T_min   0.861
_exptl_absorpt_coefficient_mu    0.967
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.6799

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements (Blessing 1995)
SADABS (see _computing_data_reduction)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.050
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            52838
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.475
_diffrn_reflns_theta_min         2.071
_diffrn_detector_area_resol_mean 8.19
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker AXS Smart 1000'
_diffrn_measurement_method       'φ- and ω-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-Ray tube (Mo)'
_diffrn_source_type              'fine focus tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.763
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.933
_reflns_number_gt                6656
_reflns_number_total             7254
_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 (see _computing_data_reduction). Includes estimated systematic errors
 of the unit cell constants from Monte Carlo simulations.
;
_computing_data_collection       'SMART-5.631 (Bruker AXS, 2003)'
_computing_data_reduction        
'SAINT V8.18C (Bruker AXS, 1997-2013),SADABS-2009_1 (Sheldrick and Bruker AXS, 1997-2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  
'encif (Wadepohl, 2009-14); encifer 1.5 (CCDC, 2014)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_shelxl_version_number           2014/7
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007-2009)'
_refine_diff_density_max         0.559
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 
;
 Flack x determined using 2692 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.006(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         7254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0305
_refine_ls_restrained_S_all      1.054
_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)+(0.0354P)²+0.6205P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0681
_refine_ls_wR_factor_ref         0.0710
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C9(H9), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C20(H20),
 C21(H21), C22(H22), C23(H23), C24(H24)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
Ni Ni -0.82736(2) -0.41891(2) -0.73533(2) 0.01140(6) Uani 1 1 d . . . . .
F1 F -0.73058(13) -0.34959(11) -0.81116(7) 0.0184(3) Uani 1 1 d . . . . .
H1 H -0.611(6) -0.399(4) -0.826(3) 0.103(18) Uiso 1 1 d . . . . .
F2 F -0.52581(18) -0.44138(16) -0.85530(10) 0.0406(4) Uani 1 1 d . . . . .
O1 O -0.97298(17) -0.67590(13) -0.86239(9) 0.0201(3) Uani 1 1 d . . . . .
O2 O -0.73188(17) -0.20684(14) -0.56107(9) 0.0205(3) Uani 1 1 d . . . . .
N1 N -0.88143(18) -0.52186(15) -0.81070(10) 0.0144(3) Uani 1 1 d . . . . .
N2 N -0.93133(17) -0.48551(15) -0.65796(10) 0.0130(3) Uani 1 1 d . . . . .
N3 N -0.76010(17) -0.31070(14) -0.66768(10) 0.0138(3) Uani 1 1 d . . . . .
C1 C -0.8492(2) -0.51622(18) -0.89416(12) 0.0161(4) Uani 1 1 d . . . . .
H1A H -0.7540 -0.4976 -0.9018 0.019 Uiso 1 1 calc R . . . .
C2 C -0.8771(2) -0.6379(2) -0.91847(13) 0.0213(4) Uani 1 1 d . . . . .
H2A H -0.9137 -0.6410 -0.9711 0.026 Uiso 1 1 calc R . . . .
H2B H -0.7960 -0.6839 -0.9164 0.026 Uiso 1 1 calc R . . . .
C3 C -0.9564(2) -0.60961(17) -0.80049(12) 0.0155(4) Uani 1 1 d . . . . .
C4 C -1.0216(2) -0.64016(17) -0.73256(13) 0.0157(3) Uani 1 1 d . . . . .
H4 H -1.0760 -0.7051 -0.7324 0.019 Uiso 1 1 calc R . . . .
C5 C -1.00914(18) -0.57949(18) -0.66716(11) 0.0138(3) Uani 1 1 d . . . . .
C6 C -1.0794(2) -0.61008(18) -0.59434(12) 0.0178(4) Uani 1 1 d . . . . .
H6A H -1.0454 -0.6815 -0.5731 0.021 Uiso 1 1 calc R . . . .
H6B H -1.1754 -0.6173 -0.6031 0.021 Uiso 1 1 calc R . . . .
C7 C -1.0495(2) -0.51286(19) -0.54094(12) 0.0190(4) Uani 1 1 d . . . . .
H7A H -1.1290 -0.4666 -0.5320 0.023 Uiso 1 1 calc R . . . .
H7B H -1.0156 -0.5400 -0.4910 0.023 Uiso 1 1 calc R . . . .
C8 C -0.9458(2) -0.44738(17) -0.58347(12) 0.0147(4) Uani 1 1 d . . . . .
C9 C -0.8797(2) -0.35979(19) -0.55194(12) 0.0171(4) Uani 1 1 d . . . . .
H9 H -0.8933 -0.3419 -0.4994 0.021 Uiso 1 1 calc R . . . .
C10 C -0.7911(2) -0.29483(18) -0.59577(12) 0.0158(4) Uani 1 1 d . . . . .
C11 C -0.6677(3) -0.14383(18) -0.62234(13) 0.0208(4) Uani 1 1 d . . . . .
H11A H -0.5795 -0.1175 -0.6061 0.025 Uiso 1 1 calc R . . . .
H11B H -0.7215 -0.0782 -0.6377 0.025 Uiso 1 1 calc R . . . .
C12 C -0.6569(2) -0.22867(17) -0.68837(12) 0.0151(4) Uani 1 1 d . . . . .
H12 H -0.6802 -0.1913 -0.7380 0.018 Uiso 1 1 calc R . . . .
C13 C -0.5217(2) -0.28090(18) -0.69443(12) 0.0164(4) Uani 1 1 d . . . . .
C14 C -0.4244(2) -0.22546(19) -0.73608(15) 0.0213(4) Uani 1 1 d . . . . .
H14 H -0.4439 -0.1553 -0.7594 0.026 Uiso 1 1 calc R . . . .
C15 C -0.2993(2) -0.2711(2) -0.74402(15) 0.0282(5) Uani 1 1 d . . . . .
H15 H -0.2345 -0.2333 -0.7737 0.034 Uiso 1 1 calc R . . . .
C16 C -0.2694(3) -0.3719(3) -0.70865(17) 0.0343(6) Uani 1 1 d . . . . .
H16 H -0.1837 -0.4033 -0.7137 0.041 Uiso 1 1 calc R . . . .
C17 C -0.3643(3) -0.4269(3) -0.66588(18) 0.0359(6) Uani 1 1 d . . . . .
H17 H -0.3434 -0.4957 -0.6411 0.043 Uiso 1 1 calc R . . . .
C18 C -0.4904(2) -0.3821(2) -0.65902(15) 0.0255(5) Uani 1 1 d . . . . .
H18 H -0.5554 -0.4208 -0.6300 0.031 Uiso 1 1 calc R . . . .
C19 C -0.9357(2) -0.43400(19) -0.93711(12) 0.0172(4) Uani 1 1 d . . . . .
C20 C -0.8916(3) -0.3917(2) -1.00740(13) 0.0229(5) Uani 1 1 d . . . . .
H20 H -0.8055 -0.4095 -1.0249 0.027 Uiso 1 1 calc R . . . .
C21 C -0.9726(3) -0.3240(2) -1.05193(14) 0.0275(5) Uani 1 1 d . . . . .
H21 H -0.9410 -0.2949 -1.0993 0.033 Uiso 1 1 calc R . . . .
C22 C -1.0994(3) -0.2984(2) -1.02768(15) 0.0282(5) Uani 1 1 d . . . . .
H22 H -1.1551 -0.2530 -1.0586 0.034 Uiso 1 1 calc R . . . .
C23 C -1.1440(2) -0.3400(2) -0.95769(16) 0.0275(5) Uani 1 1 d . . . . .
H23 H -1.2304 -0.3225 -0.9404 0.033 Uiso 1 1 calc R . . . .
C24 C -1.0623(2) -0.4073(2) -0.91303(13) 0.0218(4) Uani 1 1 d . . . . .
H24 H -1.0935 -0.4355 -0.8653 0.026 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
Ni F1 1.8410(14) . ?
Ni N1 1.8780(18) . ?
Ni N2 1.8860(18) . ?
Ni N3 1.8747(18) . ?
F1 H1 1.38(6) . ?
F2 H1 1.12(6) . ?
O1 C2 1.451(3) . ?
O1 C3 1.347(3) . ?
O2 C10 1.351(3) . ?
O2 C11 1.458(3) . ?
N1 C1 1.491(3) . ?
N1 C3 1.305(3) . ?
N2 C5 1.379(3) . ?
N2 C8 1.382(3) . ?
N3 C10 1.305(3) . ?
N3 C12 1.477(3) . ?
C1 H1A 1.0000 . ?
C1 C2 1.536(3) . ?
C1 C19 1.513(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.403(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.355(3) . ?
C5 C6 1.500(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.516(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.505(3) . ?
C8 C9 1.357(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.410(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.535(3) . ?
C12 H12 1.0000 . ?
C12 C13 1.510(3) . ?
C13 C14 1.392(3) . ?
C13 C18 1.391(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.388(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.383(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.383(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.391(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.397(3) . ?
C19 C24 1.388(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.388(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.388(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.391(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.391(3) . ?
C24 H24 0.9500 . ?
F1 F2 2.471(2) . ?

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
F1 Ni N1 87.00(7) . . ?
F1 Ni N2 177.81(7) . . ?
F1 Ni N3 87.01(7) . . ?
N1 Ni N2 93.49(8) . . ?
N3 Ni N1 173.90(8) . . ?
N3 Ni N2 92.53(8) . . ?
Ni F1 H1 115(2) . . ?
C3 O1 C2 105.76(17) . . ?
C10 O2 C11 105.72(16) . . ?
C1 N1 Ni 125.98(14) . . ?
C3 N1 Ni 126.74(15) . . ?
C3 N1 C1 107.26(17) . . ?
C5 N2 Ni 125.36(14) . . ?
C5 N2 C8 108.36(17) . . ?
C8 N2 Ni 126.26(15) . . ?
C10 N3 Ni 127.94(15) . . ?
C10 N3 C12 108.00(17) . . ?
C12 N3 Ni 124.05(14) . . ?
N1 C1 H1A 110.6 . . ?
N1 C1 C2 100.70(17) . . ?
N1 C1 C19 112.55(17) . . ?
C2 C1 H1A 110.6 . . ?
C19 C1 H1A 110.6 . . ?
C19 C1 C2 111.57(18) . . ?
O1 C2 C1 103.46(17) . . ?
O1 C2 H2A 111.1 . . ?
O1 C2 H2B 111.1 . . ?
C1 C2 H2A 111.1 . . ?
C1 C2 H2B 111.1 . . ?
H2A C2 H2B 109.0 . . ?
O1 C3 C4 117.62(18) . . ?
N1 C3 O1 115.68(19) . . ?
N1 C3 C4 126.69(19) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 C3 121.73(18) . . ?
C5 C4 H4 119.1 . . ?
N2 C5 C6 111.80(18) . . ?
C4 C5 N2 125.76(18) . . ?
C4 C5 C6 122.44(19) . . ?
C5 C6 H6A 111.0 . . ?
C5 C6 H6B 111.0 . . ?
C5 C6 C7 103.74(17) . . ?
H6A C6 H6B 109.0 . . ?
C7 C6 H6A 111.0 . . ?
C7 C6 H6B 111.0 . . ?
C6 C7 H7A 111.0 . . ?
C6 C7 H7B 111.0 . . ?
H7A C7 H7B 109.0 . . ?
C8 C7 C6 103.56(17) . . ?
C8 C7 H7A 111.0 . . ?
C8 C7 H7B 111.0 . . ?
N2 C8 C7 111.45(18) . . ?
C9 C8 N2 125.4(2) . . ?
C9 C8 C7 123.07(19) . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.23(19) . . ?
C10 C9 H9 119.4 . . ?
O2 C10 C9 117.85(19) . . ?
N3 C10 O2 115.76(19) . . ?
N3 C10 C9 126.4(2) . . ?
O2 C11 H11A 111.0 . . ?
O2 C11 H11B 111.0 . . ?
O2 C11 C12 103.94(16) . . ?
H11A C11 H11B 109.0 . . ?
C12 C11 H11A 111.0 . . ?
C12 C11 H11B 111.0 . . ?
N3 C12 C11 101.67(17) . . ?
N3 C12 H12 109.7 . . ?
N3 C12 C13 112.88(17) . . ?
C11 C12 H12 109.7 . . ?
C13 C12 C11 112.87(18) . . ?
C13 C12 H12 109.7 . . ?
C14 C13 C12 119.04(19) . . ?
C18 C13 C12 122.2(2) . . ?
C18 C13 C14 118.7(2) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.0(2) . . ?
C15 C14 H14 119.5 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.8(2) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.9(2) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.3(3) . . ?
C18 C17 H17 119.8 . . ?
C13 C18 C17 120.3(2) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C20 C19 C1 118.7(2) . . ?
C24 C19 C1 122.39(19) . . ?
C24 C19 C20 118.6(2) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.6(2) . . ?
C21 C20 H20 119.7 . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.4(2) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 120.3 . . ?
C21 C22 C23 119.3(2) . . ?
C23 C22 H22 120.3 . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 120.0(2) . . ?
C24 C23 H23 120.0 . . ?
C19 C24 C23 121.0(2) . . ?
C19 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?

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
Ni N1 C1 C2 161.34(15) . . . . ?
Ni N1 C1 C19 -79.7(2) . . . . ?
Ni N1 C3 O1 -174.92(15) . . . . ?
Ni N1 C3 C4 5.9(3) . . . . ?
Ni N2 C5 C4 1.3(3) . . . . ?
Ni N2 C5 C6 -179.74(14) . . . . ?
Ni N2 C8 C7 172.73(14) . . . . ?
Ni N2 C8 C9 -5.1(3) . . . . ?
Ni N3 C10 O2 -176.93(14) . . . . ?
Ni N3 C10 C9 2.7(3) . . . . ?
Ni N3 C12 C11 165.09(14) . . . . ?
Ni N3 C12 C13 -73.7(2) . . . . ?
F1 Ni N1 C1 -4.72(17) . . . . ?
F1 Ni N1 C3 177.13(19) . . . . ?
F1 Ni N3 C10 174.33(19) . . . . ?
F1 Ni N3 C12 -7.32(16) . . . . ?
O1 C3 C4 C5 178.96(19) . . . . ?
O2 C11 C12 N3 21.5(2) . . . . ?
O2 C11 C12 C13 -99.7(2) . . . . ?
N1 Ni N2 C5 1.64(17) . . . . ?
N1 Ni N2 C8 -176.42(17) . . . . ?
N1 C1 C2 O1 25.8(2) . . . . ?
N1 C1 C19 C20 158.98(19) . . . . ?
N1 C1 C19 C24 -27.3(3) . . . . ?
N1 C3 C4 C5 -1.9(4) . . . . ?
N2 Ni N1 C1 173.14(17) . . . . ?
N2 Ni N1 C3 -5.0(2) . . . . ?
N2 Ni N3 C10 -3.52(19) . . . . ?
N2 Ni N3 C12 174.83(16) . . . . ?
N2 C5 C6 C7 7.5(2) . . . . ?
N2 C8 C9 C10 2.9(3) . . . . ?
N3 Ni N2 C5 -177.39(16) . . . . ?
N3 Ni N2 C8 4.55(18) . . . . ?
N3 C12 C13 C14 159.68(19) . . . . ?
N3 C12 C13 C18 -21.1(3) . . . . ?
C1 N1 C3 O1 6.7(3) . . . . ?
C1 N1 C3 C4 -172.5(2) . . . . ?
C1 C19 C20 C21 174.3(2) . . . . ?
C1 C19 C24 C23 -173.6(2) . . . . ?
C2 O1 C3 N1 11.3(3) . . . . ?
C2 O1 C3 C4 -169.48(19) . . . . ?
C2 C1 C19 C20 -88.7(2) . . . . ?
C2 C1 C19 C24 85.0(2) . . . . ?
C3 O1 C2 C1 -23.2(2) . . . . ?
C3 N1 C1 C2 -20.2(2) . . . . ?
C3 N1 C1 C19 98.7(2) . . . . ?
C3 C4 C5 N2 -1.9(3) . . . . ?
C3 C4 C5 C6 179.21(19) . . . . ?
C4 C5 C6 C7 -173.49(19) . . . . ?
C5 N2 C8 C7 -5.6(2) . . . . ?
C5 N2 C8 C9 176.6(2) . . . . ?
C5 C6 C7 C8 -9.9(2) . . . . ?
C6 C7 C8 N2 10.0(2) . . . . ?
C6 C7 C8 C9 -172.1(2) . . . . ?
C7 C8 C9 C10 -174.7(2) . . . . ?
C8 N2 C5 C4 179.6(2) . . . . ?
C8 N2 C5 C6 -1.4(2) . . . . ?
C8 C9 C10 O2 178.0(2) . . . . ?
C8 C9 C10 N3 -1.6(4) . . . . ?
C10 O2 C11 C12 -19.7(2) . . . . ?
C10 N3 C12 C11 -16.3(2) . . . . ?
C10 N3 C12 C13 104.9(2) . . . . ?
C11 O2 C10 N3 10.3(3) . . . . ?
C11 O2 C10 C9 -169.36(19) . . . . ?
C11 C12 C13 C14 -85.7(2) . . . . ?
C11 C12 C13 C18 93.5(3) . . . . ?
C12 N3 C10 O2 4.5(2) . . . . ?
C12 N3 C10 C9 -175.8(2) . . . . ?
C12 C13 C14 C15 -179.1(2) . . . . ?
C12 C13 C18 C17 -179.7(2) . . . . ?
C13 C14 C15 C16 -1.5(4) . . . . ?
C14 C13 C18 C17 -0.5(4) . . . . ?
C14 C15 C16 C17 0.3(4) . . . . ?
C15 C16 C17 C18 0.8(5) . . . . ?
C16 C17 C18 C13 -0.7(4) . . . . ?
C18 C13 C14 C15 1.6(4) . . . . ?
C19 C1 C2 O1 -93.8(2) . . . . ?
C19 C20 C21 C22 -0.9(4) . . . . ?
C20 C19 C24 C23 0.0(3) . . . . ?
C20 C21 C22 C23 0.9(4) . . . . ?
C21 C22 C23 C24 -0.5(4) . . . . ?
C22 C23 C24 C19 0.1(4) . . . . ?
C24 C19 C20 C21 0.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

_diffrn_ambient_environment      'perfluoro polyether oil / N~2~'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_specimen_support 'polyimid foil'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            CCD-PXL-KAF2
####################################################################### 
# 
# 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_ga_jw1
_database_code_depnum_ccdc_archive 'CCDC 1427463'
_audit_update_record             
;
2015-09-25 deposited with the CCDC.
2015-11-09 downloaded from the CCDC.
;
_audit_creation_date             2014-07-25

_audit_block_code                ga_jw1
_audit_block_refno               2115
_audit_block_usercomment         JW16


_shelxl_version_number           2014-3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C18 H26 F N3 Ni O2, 0.5(C7 H8), 0.5(H2 O)'
_chemical_formula_sum            'C21.50 H31 F N3 Ni O2.50'
_chemical_properties_physical    air-sensitive
_chemical_formula_weight         449.20
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_h-m   'P 21 21 21'
_symmetry_int_tables_number      19

_chemical_absolute_configuration ad
_chemical_melting_point          ?
_exptl_crystal_description       irregular
_exptl_crystal_colour            red
_diffrn_ambient_temperature      100(1)
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   10.777(8)
_cell_length_b                   10.970(8)
_cell_length_c                   36.58(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4325(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7648
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.75
_cell_measurement_theta_min      2.19
_shelx_estimated_absorpt_T_max   0.889
_shelx_estimated_absorpt_T_min   0.836
_exptl_absorpt_coefficient_mu    0.930
_exptl_absorpt_correction_T_max  0.8623
_exptl_absorpt_correction_T_min  0.7854

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements (Blessing 1995)
SADABS (see _computing_data_reduction)
;
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_number            110129
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.432
_diffrn_reflns_theta_min         1.113
_diffrn_detector_area_resol_mean 8.19
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker AXS Smart 1000'
_diffrn_measurement_method       'φ- and ω-scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-Ray tube (Mo)'
_diffrn_source_type              'fine focus tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.930
_reflns_number_gt                13565
_reflns_number_total             14769
_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 (see _computing_data_reduction). Includes estimated systematic errors
 of the unit cell constants from Monte Carlo simulations.
;
_computing_data_collection       'SMART-5.631 (Bruker AXS, 2003)'
_computing_data_reduction        
'SAINT V8.34A (Bruker AXS, 1997-2013), SADABS-2014_2 (Sheldrick and Bruker AXS, 1997-2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  
'encif (Wadepohl, 2009-14); encifer 1.4 (CCDC, 2011)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007-2009)'
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 
;
 Flack x determined using 5642 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     648
_refine_ls_number_reflns         14769
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0297
_refine_ls_restrained_S_all      1.053
_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)+(0.0338P)²+0.4639P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0640
_refine_ls_wR_factor_ref         0.0666
_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 Idealised Me refined as rotating group with stretchable bonds:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C), C64(H64A,H64B,H64C), C65(H65A,H65B,H65C), C67(H67A,H67B,H67C), C68(H68A,
 H68B,H68C), C87(H87A,H87B,H87C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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 0.50591(2) 0.66321(2) 0.35640(2) 0.01147(5) Uani 1 1 d . . . . .
F1 F 0.66634(11) 0.69976(11) 0.36866(3) 0.0180(2) Uani 1 1 d . . . . .
O1 O 0.45681(14) 0.36642(13) 0.42163(4) 0.0201(3) Uani 1 1 d . . . . .
O2 O 0.44804(15) 0.93895(14) 0.28416(4) 0.0195(3) Uani 1 1 d . . . . .
N1 N 0.51169(15) 0.53604(14) 0.39115(4) 0.0139(3) Uani 1 1 d . . . . .
N2 N 0.34170(15) 0.62458(15) 0.34294(4) 0.0150(3) Uani 1 1 d . . . . .
N3 N 0.51289(16) 0.79441(14) 0.32320(4) 0.0137(3) Uani 1 1 d . . . . .
C1 C 0.60274(19) 0.52856(18) 0.42146(5) 0.0137(3) Uani 1 1 d . . . . .
H1 H 0.681(3) 0.533(2) 0.4122(6) 0.016 Uiso 1 1 d R . . . .
C2 C 0.5764(2) 0.40094(18) 0.43727(6) 0.0178(4) Uani 1 1 d . . . . .
H2A H 0.632(3) 0.342(2) 0.4311(7) 0.021 Uiso 1 1 d R . . . .
H2B H 0.568(2) 0.396(2) 0.4645(7) 0.021 Uiso 1 1 d R . . . .
C3 C 0.43246(19) 0.44735(17) 0.39472(6) 0.0164(3) Uani 1 1 d . . . . .
C4 C 0.3221(2) 0.43020(19) 0.37431(6) 0.0187(4) Uani 1 1 d . . . . .
H4 H 0.277(3) 0.359(3) 0.3788(7) 0.022 Uiso 1 1 d R . . . .
C5 C 0.28052(19) 0.51794(19) 0.35112(5) 0.0176(4) Uani 1 1 d . . . . .
C6 C 0.1574(2) 0.5114(2) 0.33133(6) 0.0240(4) Uani 1 1 d . . . . .
H6A H 0.088(3) 0.472(3) 0.3472(8) 0.029 Uiso 1 1 d R . . . .
H6B H 0.168(3) 0.464(3) 0.3115(8) 0.029 Uiso 1 1 d R . . . .
C7 C 0.1334(2) 0.6456(2) 0.32221(6) 0.0256(5) Uani 1 1 d . . . . .
H7A H 0.098(3) 0.651(3) 0.2984(8) 0.031 Uiso 1 1 d R . . . .
H7B H 0.077(3) 0.685(3) 0.3414(8) 0.031 Uiso 1 1 d R . . . .
C8 C 0.26236(18) 0.69952(19) 0.32355(5) 0.0175(4) Uani 1 1 d . . . . .
C9 C 0.2944(2) 0.8061(2) 0.30755(6) 0.0194(4) Uani 1 1 d . . . . .
H9 H 0.234(3) 0.853(3) 0.2974(7) 0.023 Uiso 1 1 d R . . . .
C10 C 0.41957(19) 0.84465(18) 0.30643(5) 0.0158(3) Uani 1 1 d . . . . .
C11 C 0.5805(2) 0.96186(19) 0.28867(6) 0.0181(4) Uani 1 1 d . . . . .
H11A H 0.592(2) 1.033(3) 0.3024(7) 0.022 Uiso 1 1 d R . . . .
H11B H 0.615(2) 0.971(2) 0.2639(7) 0.022 Uiso 1 1 d R . . . .
C12 C 0.62985(19) 0.84909(17) 0.30909(5) 0.0144(3) Uani 1 1 d . . . . .
H12 H 0.683(2) 0.872(2) 0.3313(7) 0.017 Uiso 1 1 d R . . . .
C13 C 0.70082(18) 0.75798(18) 0.28508(5) 0.0155(3) Uani 1 1 d . . . . .
H13 H 0.710(2) 0.693(2) 0.3004(7) 0.019 Uiso 1 1 d R . . . .
C14 C 0.6283(2) 0.7200(2) 0.25107(6) 0.0227(4) Uani 1 1 d . . . . .
H14A H 0.5488(14) 0.6928(16) 0.25799(13) 0.034 Uiso 1 1 calc GR . . . .
H14B H 0.6707(11) 0.6566(15) 0.2391(3) 0.034 Uiso 1 1 calc GR . . . .
H14C H 0.6206(14) 0.7872(12) 0.2352(3) 0.034 Uiso 1 1 calc GR . . . .
C15 C 0.8289(2) 0.8092(2) 0.27518(6) 0.0251(5) Uani 1 1 d . . . . .
H15A H 0.8190(3) 0.8866(15) 0.2628(5) 0.038 Uiso 1 1 calc GR . . . .
H15B H 0.8713(10) 0.7526(13) 0.2592(5) 0.038 Uiso 1 1 calc GR . . . .
H15C H 0.8770(10) 0.8207(16) 0.2972(4) 0.038 Uiso 1 1 calc GR . . . .
C16 C 0.5825(2) 0.63359(18) 0.44859(5) 0.0166(4) Uani 1 1 d . . . . .
H16 H 0.597(2) 0.707(2) 0.4351(7) 0.020 Uiso 1 1 d R . . . .
C17 C 0.4503(2) 0.6352(2) 0.46412(6) 0.0227(4) Uani 1 1 d . . . . .
H17A H 0.3935(10) 0.6479(17) 0.4451(3) 0.034 Uiso 1 1 calc GR . . . .
H17B H 0.4431(6) 0.6983(15) 0.4813(5) 0.034 Uiso 1 1 calc GR . . . .
H17C H 0.4336(7) 0.5604(14) 0.4755(5) 0.034 Uiso 1 1 calc GR . . . .
C18 C 0.6818(2) 0.6287(2) 0.47858(6) 0.0213(4) Uani 1 1 d . . . . .
H18A H 0.6738(11) 0.5551(14) 0.4919(4) 0.032 Uiso 1 1 calc GR . . . .
H18B H 0.6713(11) 0.6956(14) 0.4946(4) 0.032 Uiso 1 1 calc GR . . . .
H18C H 0.7615(13) 0.6324(17) 0.46778(18) 0.032 Uiso 1 1 calc GR . . . .
Ni51 Ni 0.35615(2) 0.23307(2) 0.60554(2) 0.01216(5) Uani 1 1 d . . . . .
F51 F 0.42477(12) 0.08608(11) 0.61740(3) 0.0183(2) Uani 1 1 d . . . . .
O51 O 0.06013(13) 0.22286(15) 0.67510(4) 0.0205(3) Uani 1 1 d . . . . .
O52 O 0.61821(14) 0.34101(15) 0.53225(4) 0.0229(3) Uani 1 1 d . . . . .
N51 N 0.23492(15) 0.20251(14) 0.64147(4) 0.0145(3) Uani 1 1 d . . . . .
N52 N 0.28303(16) 0.38344(15) 0.59248(4) 0.0155(3) Uani 1 1 d . . . . .
N53 N 0.48494(15) 0.25136(14) 0.57136(4) 0.0148(3) Uani 1 1 d . . . . .
C51 C 0.24848(18) 0.11075(18) 0.67111(5) 0.0143(3) Uani 1 1 d . . . . .
H51 H 0.270(2) 0.031(2) 0.6605(6) 0.017 Uiso 1 1 d R . . . .
C52 C 0.11771(19) 0.1111(2) 0.68815(6) 0.0179(4) Uani 1 1 d . . . . .
H52A H 0.069(2) 0.048(3) 0.6796(7) 0.021 Uiso 1 1 d R . . . .
H52B H 0.111(2) 0.110(2) 0.7139(7) 0.021 Uiso 1 1 d R . . . .
C53 C 0.13248(18) 0.26271(18) 0.64724(5) 0.0167(3) Uani 1 1 d . . . . .
C54 C 0.0937(2) 0.3688(2) 0.62842(6) 0.0211(4) Uani 1 1 d . . . . .
H54 H 0.018(3) 0.397(3) 0.6340(7) 0.025 Uiso 1 1 d R . . . .
C55 C 0.1683(2) 0.42439(17) 0.60366(6) 0.0190(4) Uani 1 1 d . . . . .
C56 C 0.1346(2) 0.5425(2) 0.58485(6) 0.0246(5) Uani 1 1 d . . . . .
H56A H 0.101(3) 0.598(3) 0.6008(8) 0.029 Uiso 1 1 d R . . . .
H56B H 0.077(3) 0.526(3) 0.5639(8) 0.029 Uiso 1 1 d R . . . .
C57 C 0.2584(2) 0.5841(2) 0.56910(7) 0.0252(5) Uani 1 1 d . . . . .
H57A H 0.248(3) 0.613(3) 0.5442(8) 0.030 Uiso 1 1 d R . . . .
H57B H 0.297(3) 0.641(3) 0.5828(8) 0.030 Uiso 1 1 d R . . . .
C58 C 0.3371(2) 0.47055(17) 0.57023(5) 0.0182(4) Uani 1 1 d . . . . .
C59 C 0.4463(2) 0.45889(19) 0.55239(6) 0.0212(4) Uani 1 1 d . . . . .
H59 H 0.488(3) 0.529(3) 0.5382(7) 0.025 Uiso 1 1 d R . . . .
C60 C 0.5145(2) 0.34870(18) 0.55322(5) 0.0177(4) Uani 1 1 d . . . . .
C61 C 0.6734(2) 0.2233(2) 0.54073(6) 0.0231(4) Uani 1 1 d . . . . .
H61A H 0.741(3) 0.238(3) 0.5563(7) 0.028 Uiso 1 1 d R . . . .
H61B H 0.697(3) 0.190(3) 0.5179(8) 0.028 Uiso 1 1 d R . . . .
C62 C 0.56888(18) 0.15148(19) 0.55938(5) 0.0168(4) Uani 1 1 d . . . . .
H62 H 0.597(2) 0.111(3) 0.5794(7) 0.020 Uiso 1 1 d R . . . .
C63 C 0.4992(2) 0.06149(18) 0.53454(6) 0.0200(4) Uani 1 1 d . . . . .
H63 H 0.433(3) 0.035(3) 0.5476(7) 0.024 Uiso 1 1 d R . . . .
C64 C 0.4511(2) 0.1202(2) 0.49939(6) 0.0277(5) Uani 1 1 d . . . . .
H64A H 0.4058(17) 0.1863(16) 0.50497(12) 0.042 Uiso 1 1 calc GR . . . .
H64B H 0.4037(17) 0.0665(12) 0.4872(4) 0.042 Uiso 1 1 calc GR . . . .
H64C H 0.5156(12) 0.1422(17) 0.4853(4) 0.042 Uiso 1 1 calc GR . . . .
C65 C 0.5815(3) -0.0488(2) 0.52644(7) 0.0350(6) Uani 1 1 d . . . . .
H65A H 0.6531(17) -0.0231(6) 0.5135(6) 0.052 Uiso 1 1 calc GR . . . .
H65B H 0.5367(11) -0.1058(14) 0.5121(6) 0.052 Uiso 1 1 calc GR . . . .
H65C H 0.6058(17) -0.0859(14) 0.5487(4) 0.052 Uiso 1 1 calc GR . . . .
C66 C 0.35330(19) 0.14844(18) 0.69741(5) 0.0157(3) Uani 1 1 d . . . . .
H66 H 0.425(2) 0.156(2) 0.6832(7) 0.019 Uiso 1 1 d R . . . .
C67 C 0.3265(2) 0.2698(2) 0.71664(5) 0.0201(4) Uani 1 1 d . . . . .
H67A H 0.3069(16) 0.3320(10) 0.6984(3) 0.030 Uiso 1 1 calc GR . . . .
H67B H 0.3994(13) 0.2951(9) 0.7306(4) 0.030 Uiso 1 1 calc GR . . . .
H67C H 0.2560(15) 0.2599(5) 0.7332(4) 0.030 Uiso 1 1 calc GR . . . .
C68 C 0.3778(2) 0.0455(2) 0.72487(6) 0.0210(4) Uani 1 1 d . . . . .
H68A H 0.3062(13) 0.0307(11) 0.7384(4) 0.031 Uiso 1 1 calc GR . . . .
H68B H 0.4419(15) 0.0682(8) 0.7405(4) 0.031 Uiso 1 1 calc GR . . . .
H68C H 0.4003(17) -0.0250(13) 0.7123(2) 0.031 Uiso 1 1 calc GR . . . .
C81 C 0.6654(2) 0.5616(2) 0.61563(6) 0.0239(4) Uani 1 1 d . . . . .
C82 C 0.7569(2) 0.4747(2) 0.62247(7) 0.0290(5) Uani 1 1 d . . . . .
H82 H 0.833(3) 0.479(3) 0.6055(8) 0.035 Uiso 1 1 d R . . . .
C83 C 0.7413(3) 0.3873(2) 0.64969(8) 0.0334(6) Uani 1 1 d . . . . .
H83 H 0.797(3) 0.331(3) 0.6527(8) 0.040 Uiso 1 1 d R . . . .
C84 C 0.6320(3) 0.3844(2) 0.66952(8) 0.0344(6) Uani 1 1 d . . . . .
H84 H 0.614(3) 0.328(3) 0.6885(9) 0.041 Uiso 1 1 d R . . . .
C85 C 0.5394(3) 0.4683(3) 0.66233(7) 0.0316(5) Uani 1 1 d . . . . .
H85 H 0.465(3) 0.465(3) 0.6736(8) 0.038 Uiso 1 1 d R . . . .
C86 C 0.5561(2) 0.5564(2) 0.63564(7) 0.0257(5) Uani 1 1 d . . . . .
H86 H 0.496(3) 0.612(3) 0.6292(8) 0.031 Uiso 1 1 d R . . . .
C87 C 0.6850(3) 0.6605(3) 0.58763(7) 0.0369(6) Uani 1 1 d . . . . .
H87A H 0.6041(16) 0.7007(15) 0.5821(4) 0.055 Uiso 1 1 calc GR . . . .
H87B H 0.7195(19) 0.6241(8) 0.5648(5) 0.055 Uiso 1 1 calc GR . . . .
H87C H 0.7443(19) 0.7221(16) 0.5974(3) 0.055 Uiso 1 1 calc GR . . . .
O4 O 0.40695(16) 0.83858(17) 0.61256(6) 0.0320(4) Uani 1 1 d . . . . .
H4A H 0.413(4) 0.916(4) 0.6116(10) 0.060(11) Uiso 1 1 d . . . . .
H4B H 0.331(4) 0.836(3) 0.6197(10) 0.055(11) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 F1 1.8308(17) . ?
Ni1 N1 1.8884(18) . ?
Ni1 N2 1.885(2) . ?
Ni1 N3 1.8847(18) . ?
O1 C2 1.460(3) . ?
O1 C3 1.351(2) . ?
O2 C10 1.352(2) . ?
O2 C11 1.458(3) . ?
N1 C1 1.483(3) . ?
N1 C3 1.301(3) . ?
N2 C5 1.376(3) . ?
N2 C8 1.382(3) . ?
N3 C10 1.301(3) . ?
N3 C12 1.488(3) . ?
C1 H1 0.91(3) . ?
C1 C2 1.541(3) . ?
C1 C16 1.536(3) . ?
C2 H2A 0.91(3) . ?
C2 H2B 1.00(3) . ?
C3 C4 1.417(3) . ?
C4 H4 0.94(3) . ?
C4 C5 1.359(3) . ?
C5 C6 1.514(3) . ?
C6 H6A 1.04(3) . ?
C6 H6B 0.90(3) . ?
C6 C7 1.531(4) . ?
C7 H7A 0.95(3) . ?
C7 H7B 1.02(3) . ?
C7 C8 1.512(3) . ?
C8 C9 1.353(3) . ?
C9 H9 0.91(3) . ?
C9 C10 1.415(3) . ?
C11 H11A 0.93(3) . ?
C11 H11B 0.99(3) . ?
C11 C12 1.540(3) . ?
C12 H12 1.02(3) . ?
C12 C13 1.535(3) . ?
C13 H13 0.91(3) . ?
C13 C14 1.527(3) . ?
C13 C15 1.533(3) . ?
C14 H14A 0.942(16) . ?
C14 H14B 0.942(16) . ?
C14 H14C 0.942(16) . ?
C15 H15A 0.967(16) . ?
C15 H15B 0.967(16) . ?
C15 H15C 0.967(16) . ?
C16 H16 0.96(3) . ?
C16 C17 1.533(3) . ?
C16 C18 1.534(3) . ?
C17 H17A 0.937(16) . ?
C17 H17B 0.937(16) . ?
C17 H17C 0.937(16) . ?
C18 H18A 0.946(15) . ?
C18 H18B 0.946(15) . ?
C18 H18C 0.946(15) . ?
Ni51 F51 1.8263(16) . ?
Ni51 N51 1.8834(19) . ?
Ni51 N52 1.890(2) . ?
Ni51 N53 1.8788(18) . ?
O51 C52 1.455(3) . ?
O51 C53 1.356(3) . ?
O52 C60 1.358(3) . ?
O52 C61 1.455(3) . ?
N51 C51 1.487(3) . ?
N51 C53 1.304(3) . ?
N52 C55 1.378(3) . ?
N52 C58 1.384(3) . ?
N53 C60 1.297(3) . ?
N53 C62 1.487(3) . ?
C51 H51 0.99(3) . ?
C51 C52 1.541(3) . ?
C51 C66 1.540(3) . ?
C52 H52A 0.92(3) . ?
C52 H52B 0.94(3) . ?
C53 C54 1.415(3) . ?
C54 H54 0.90(3) . ?
C54 C55 1.355(3) . ?
C55 C56 1.511(3) . ?
C56 H56A 0.92(3) . ?
C56 H56B 1.01(3) . ?
C56 C57 1.523(4) . ?
C57 H57A 0.97(3) . ?
C57 H57B 0.90(3) . ?
C57 C58 1.508(3) . ?
C58 C59 1.352(3) . ?
C59 H59 1.03(3) . ?
C59 C60 1.415(3) . ?
C61 H61A 0.94(3) . ?
C61 H61B 0.95(3) . ?
C61 C62 1.535(3) . ?
C62 H62 0.91(3) . ?
C62 C63 1.538(3) . ?
C63 H63 0.91(3) . ?
C63 C64 1.528(3) . ?
C63 C65 1.529(3) . ?
C64 H64A 0.898(17) . ?
C64 H64B 0.898(17) . ?
C64 H64C 0.898(17) . ?
C65 H65A 0.948(18) . ?
C65 H65B 0.948(18) . ?
C65 H65C 0.948(18) . ?
C66 H66 0.93(3) . ?
C66 C67 1.534(3) . ?
C66 C68 1.534(3) . ?
C67 H67A 0.977(15) . ?
C67 H67B 0.977(15) . ?
C67 H67C 0.977(15) . ?
C68 H68A 0.931(16) . ?
C68 H68B 0.931(16) . ?
C68 H68C 0.931(16) . ?
C81 C82 1.395(4) . ?
C81 C86 1.388(3) . ?
C81 C87 1.506(3) . ?
C82 H82 1.03(3) . ?
C82 C83 1.392(4) . ?
C83 H83 0.87(3) . ?
C83 C84 1.384(4) . ?
C84 H84 0.95(3) . ?
C84 C85 1.382(4) . ?
C85 H85 0.90(3) . ?
C85 C86 1.386(4) . ?
C86 H86 0.92(3) . ?
C87 H87A 0.998(19) . ?
C87 H87B 0.998(19) . ?
C87 H87C 1.00(2) . ?
O4 H4A 0.85(4) . ?
O4 H4B 0.86(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 Ni1 N1 88.04(6) . . ?
F1 Ni1 N2 178.96(6) . . ?
F1 Ni1 N3 87.30(6) . . ?
N2 Ni1 N1 92.33(7) . . ?
N3 Ni1 N1 175.28(7) . . ?
N3 Ni1 N2 92.34(7) . . ?
C3 O1 C2 106.64(15) . . ?
C10 O2 C11 106.60(16) . . ?
C1 N1 Ni1 124.47(12) . . ?
C3 N1 Ni1 126.74(14) . . ?
C3 N1 C1 108.55(16) . . ?
C5 N2 Ni1 125.75(14) . . ?
C5 N2 C8 108.71(17) . . ?
C8 N2 Ni1 125.53(14) . . ?
C10 N3 Ni1 126.63(14) . . ?
C10 N3 C12 108.69(16) . . ?
C12 N3 Ni1 124.41(13) . . ?
N1 C1 H1 109.5(15) . . ?
N1 C1 C2 102.07(16) . . ?
N1 C1 C16 110.32(16) . . ?
C2 C1 H1 110.8(16) . . ?
C16 C1 H1 109.5(16) . . ?
C16 C1 C2 114.38(16) . . ?
O1 C2 C1 104.54(16) . . ?
O1 C2 H2A 107.5(17) . . ?
O1 C2 H2B 107.5(15) . . ?
C1 C2 H2A 115.7(17) . . ?
C1 C2 H2B 115.8(16) . . ?
H2A C2 H2B 105(2) . . ?
O1 C3 C4 117.36(17) . . ?
N1 C3 O1 115.90(18) . . ?
N1 C3 C4 126.70(19) . . ?
C3 C4 H4 117.1(16) . . ?
C5 C4 C3 120.76(19) . . ?
C5 C4 H4 122.0(16) . . ?
N2 C5 C6 110.88(18) . . ?
C4 C5 N2 125.46(19) . . ?
C4 C5 C6 123.65(19) . . ?
C5 C6 H6A 112.6(15) . . ?
C5 C6 H6B 107.3(19) . . ?
C5 C6 C7 101.95(18) . . ?
H6A C6 H6B 108(2) . . ?
C7 C6 H6A 113.6(16) . . ?
C7 C6 H6B 113.8(18) . . ?
C6 C7 H7A 109.4(18) . . ?
C6 C7 H7B 110.9(17) . . ?
H7A C7 H7B 111(2) . . ?
C8 C7 C6 102.35(18) . . ?
C8 C7 H7A 111.7(18) . . ?
C8 C7 H7B 111.0(17) . . ?
N2 C8 C7 110.65(18) . . ?
C9 C8 N2 125.36(19) . . ?
C9 C8 C7 123.99(19) . . ?
C8 C9 H9 118.6(18) . . ?
C8 C9 C10 120.93(19) . . ?
C10 C9 H9 120.4(18) . . ?
O2 C10 C9 117.54(18) . . ?
N3 C10 O2 115.65(18) . . ?
N3 C10 C9 126.69(19) . . ?
O2 C11 H11A 109.7(17) . . ?
O2 C11 H11B 106.6(15) . . ?
O2 C11 C12 104.76(16) . . ?
H11A C11 H11B 111(2) . . ?
C12 C11 H11A 111.1(17) . . ?
C12 C11 H11B 113.0(15) . . ?
N3 C12 C11 101.49(16) . . ?
N3 C12 H12 107.3(14) . . ?
N3 C12 C13 110.98(16) . . ?
C11 C12 H12 112.2(15) . . ?
C13 C12 C11 114.72(16) . . ?
C13 C12 H12 109.7(15) . . ?
C12 C13 H13 102.3(16) . . ?
C14 C13 C12 112.86(17) . . ?
C14 C13 H13 109.8(16) . . ?
C14 C13 C15 111.61(17) . . ?
C15 C13 C12 110.18(17) . . ?
C15 C13 H13 109.7(17) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 C16 H16 105.9(16) . . ?
C17 C16 C1 112.34(17) . . ?
C17 C16 H16 109.6(16) . . ?
C17 C16 C18 112.55(17) . . ?
C18 C16 C1 109.67(17) . . ?
C18 C16 H16 106.4(16) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
F51 Ni51 N51 87.60(7) . . ?
F51 Ni51 N52 178.75(7) . . ?
F51 Ni51 N53 87.32(7) . . ?
N51 Ni51 N52 92.44(8) . . ?
N53 Ni51 N51 174.83(7) . . ?
N53 Ni51 N52 92.67(8) . . ?
C53 O51 C52 105.86(15) . . ?
C60 O52 C61 105.75(15) . . ?
C51 N51 Ni51 124.14(13) . . ?
C53 N51 Ni51 127.60(14) . . ?
C53 N51 C51 107.96(16) . . ?
C55 N52 Ni51 125.72(14) . . ?
C55 N52 C58 109.10(17) . . ?
C58 N52 Ni51 125.18(15) . . ?
C60 N53 Ni51 127.59(14) . . ?
C60 N53 C62 107.83(17) . . ?
C62 N53 Ni51 124.53(12) . . ?
N51 C51 H51 109.8(14) . . ?
N51 C51 C52 101.74(16) . . ?
N51 C51 C66 110.23(16) . . ?
C52 C51 H51 112.0(15) . . ?
C66 C51 H51 108.2(15) . . ?
C66 C51 C52 114.67(16) . . ?
O51 C52 C51 105.03(16) . . ?
O51 C52 H52A 105.9(17) . . ?
O51 C52 H52B 107.8(17) . . ?
C51 C52 H52A 112.5(17) . . ?
C51 C52 H52B 117.9(16) . . ?
H52A C52 H52B 107(2) . . ?
O51 C53 C54 117.47(18) . . ?
N51 C53 O51 116.44(18) . . ?
N51 C53 C54 126.00(19) . . ?
C53 C54 H54 116.2(18) . . ?
C55 C54 C53 121.3(2) . . ?
C55 C54 H54 122.4(18) . . ?
N52 C55 C56 111.1(2) . . ?
C54 C55 N52 125.71(19) . . ?
C54 C55 C56 123.2(2) . . ?
C55 C56 H56A 112.1(19) . . ?
C55 C56 H56B 109.8(18) . . ?
C55 C56 C57 102.65(19) . . ?
H56A C56 H56B 111(2) . . ?
C57 C56 H56A 112.4(19) . . ?
C57 C56 H56B 108.0(17) . . ?
C56 C57 H57A 110.9(18) . . ?
C56 C57 H57B 113.8(19) . . ?
H57A C57 H57B 110(3) . . ?
C58 C57 C56 103.54(18) . . ?
C58 C57 H57A 111.2(18) . . ?
C58 C57 H57B 107.1(19) . . ?
N52 C58 C57 110.5(2) . . ?
C59 C58 N52 125.80(19) . . ?
C59 C58 C57 123.7(2) . . ?
C58 C59 H59 123.3(16) . . ?
C58 C59 C60 121.52(19) . . ?
C60 C59 H59 115.1(16) . . ?
O52 C60 C59 117.93(18) . . ?
N53 C60 O52 116.11(18) . . ?
N53 C60 C59 125.9(2) . . ?
O52 C61 H61A 107.1(18) . . ?
O52 C61 H61B 105.3(17) . . ?
O52 C61 C62 104.48(17) . . ?
H61A C61 H61B 113(2) . . ?
C62 C61 H61A 113.0(17) . . ?
C62 C61 H61B 112.8(18) . . ?
N53 C62 C61 101.49(17) . . ?
N53 C62 H62 108.9(17) . . ?
N53 C62 C63 110.49(17) . . ?
C61 C62 H62 111.4(17) . . ?
C61 C62 C63 115.20(18) . . ?
C63 C62 H62 109.0(18) . . ?
C62 C63 H63 106.3(17) . . ?
C64 C63 C62 113.09(18) . . ?
C64 C63 H63 108.3(17) . . ?
C64 C63 C65 111.52(19) . . ?
C65 C63 C62 109.8(2) . . ?
C65 C63 H63 107.5(18) . . ?
C63 C64 H64A 109.5 . . ?
C63 C64 H64B 109.5 . . ?
C63 C64 H64C 109.5 . . ?
H64A C64 H64B 109.5 . . ?
H64A C64 H64C 109.5 . . ?
H64B C64 H64C 109.5 . . ?
C63 C65 H65A 109.5 . . ?
C63 C65 H65B 109.5 . . ?
C63 C65 H65C 109.5 . . ?
H65A C65 H65B 109.5 . . ?
H65A C65 H65C 109.5 . . ?
H65B C65 H65C 109.5 . . ?
C51 C66 H66 106.2(16) . . ?
C67 C66 C51 112.41(17) . . ?
C67 C66 H66 109.8(17) . . ?
C67 C66 C68 111.82(17) . . ?
C68 C66 C51 109.73(17) . . ?
C68 C66 H66 106.5(16) . . ?
C66 C67 H67A 109.5 . . ?
C66 C67 H67B 109.5 . . ?
C66 C67 H67C 109.5 . . ?
H67A C67 H67B 109.5 . . ?
H67A C67 H67C 109.5 . . ?
H67B C67 H67C 109.5 . . ?
C66 C68 H68A 109.5 . . ?
C66 C68 H68B 109.5 . . ?
C66 C68 H68C 109.5 . . ?
H68A C68 H68B 109.5 . . ?
H68A C68 H68C 109.5 . . ?
H68B C68 H68C 109.5 . . ?
C82 C81 C87 121.0(2) . . ?
C86 C81 C82 118.5(2) . . ?
C86 C81 C87 120.5(2) . . ?
C81 C82 H82 115.1(17) . . ?
C83 C82 C81 120.9(2) . . ?
C83 C82 H82 124.0(17) . . ?
C82 C83 H83 120(2) . . ?
C84 C83 C82 119.6(2) . . ?
C84 C83 H83 120(2) . . ?
C83 C84 H84 125(2) . . ?
C85 C84 C83 119.9(2) . . ?
C85 C84 H84 115(2) . . ?
C84 C85 H85 122(2) . . ?
C84 C85 C86 120.3(3) . . ?
C86 C85 H85 118(2) . . ?
C81 C86 H86 116.0(19) . . ?
C85 C86 C81 120.7(2) . . ?
C85 C86 H86 123.2(19) . . ?
C81 C87 H87A 109.5 . . ?
C81 C87 H87B 109.5 . . ?
C81 C87 H87C 109.5 . . ?
H87A C87 H87B 109.5 . . ?
H87A C87 H87C 109.5 . . ?
H87B C87 H87C 109.5 . . ?
H4A O4 H4B 97(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ni1 N1 C1 C2 -172.53(13) . . . . ?
Ni1 N1 C1 C16 65.5(2) . . . . ?
Ni1 N1 C3 O1 179.63(13) . . . . ?
Ni1 N1 C3 C4 -2.9(3) . . . . ?
Ni1 N2 C5 C4 9.5(3) . . . . ?
Ni1 N2 C5 C6 -171.81(14) . . . . ?
Ni1 N2 C8 C7 -172.38(14) . . . . ?
Ni1 N2 C8 C9 8.1(3) . . . . ?
Ni1 N3 C10 O2 179.23(12) . . . . ?
Ni1 N3 C10 C9 -4.8(3) . . . . ?
Ni1 N3 C12 C11 -171.49(12) . . . . ?
Ni1 N3 C12 C13 66.16(19) . . . . ?
F1 Ni1 N1 C1 19.50(15) . . . . ?
F1 Ni1 N1 C3 -166.77(17) . . . . ?
F1 Ni1 N3 C10 -167.04(16) . . . . ?
F1 Ni1 N3 C12 19.56(14) . . . . ?
O1 C3 C4 C5 168.95(19) . . . . ?
O2 C11 C12 N3 -16.29(19) . . . . ?
O2 C11 C12 C13 103.44(19) . . . . ?
N1 Ni1 N2 C5 -15.21(16) . . . . ?
N1 Ni1 N2 C8 164.01(16) . . . . ?
N1 C1 C2 O1 -14.80(19) . . . . ?
N1 C1 C16 C17 57.2(2) . . . . ?
N1 C1 C16 C18 -176.87(16) . . . . ?
N1 C3 C4 C5 -8.4(3) . . . . ?
N2 Ni1 N1 C1 -161.47(15) . . . . ?
N2 Ni1 N1 C3 12.26(17) . . . . ?
N2 Ni1 N3 C10 13.93(17) . . . . ?
N2 Ni1 N3 C12 -159.46(14) . . . . ?
N2 C5 C6 C7 -20.2(2) . . . . ?
N2 C8 C9 C10 6.4(3) . . . . ?
N3 Ni1 N2 C5 165.40(16) . . . . ?
N3 Ni1 N2 C8 -15.38(16) . . . . ?
N3 C12 C13 C14 62.3(2) . . . . ?
N3 C12 C13 C15 -172.20(16) . . . . ?
C1 N1 C3 O1 -5.8(2) . . . . ?
C1 N1 C3 C4 171.61(19) . . . . ?
C2 O1 C3 N1 -4.5(2) . . . . ?
C2 O1 C3 C4 177.80(17) . . . . ?
C2 C1 C16 C17 -57.2(2) . . . . ?
C2 C1 C16 C18 68.8(2) . . . . ?
C3 O1 C2 C1 12.2(2) . . . . ?
C3 N1 C1 C2 12.8(2) . . . . ?
C3 N1 C1 C16 -109.19(18) . . . . ?
C3 C4 C5 N2 4.9(3) . . . . ?
C3 C4 C5 C6 -173.73(19) . . . . ?
C4 C5 C6 C7 158.5(2) . . . . ?
C5 N2 C8 C7 6.9(2) . . . . ?
C5 N2 C8 C9 -172.5(2) . . . . ?
C5 C6 C7 C8 22.2(2) . . . . ?
C6 C7 C8 N2 -19.1(2) . . . . ?
C6 C7 C8 C9 160.4(2) . . . . ?
C7 C8 C9 C10 -173.0(2) . . . . ?
C8 N2 C5 C4 -169.9(2) . . . . ?
C8 N2 C5 C6 8.9(2) . . . . ?
C8 C9 C10 O2 167.50(18) . . . . ?
C8 C9 C10 N3 -8.4(3) . . . . ?
C10 O2 C11 C12 13.5(2) . . . . ?
C10 N3 C12 C11 14.10(19) . . . . ?
C10 N3 C12 C13 -108.24(18) . . . . ?
C11 O2 C10 N3 -4.9(2) . . . . ?
C11 O2 C10 C9 178.77(18) . . . . ?
C11 C12 C13 C14 -52.0(2) . . . . ?
C11 C12 C13 C15 73.5(2) . . . . ?
C12 N3 C10 O2 -6.5(2) . . . . ?
C12 N3 C10 C9 169.44(19) . . . . ?
C16 C1 C2 O1 104.33(19) . . . . ?
Ni51 N51 C51 C52 -171.83(13) . . . . ?
Ni51 N51 C51 C66 66.10(19) . . . . ?
Ni51 N51 C53 O51 -179.74(13) . . . . ?
Ni51 N51 C53 C54 -3.3(3) . . . . ?
Ni51 N52 C55 C54 6.3(3) . . . . ?
Ni51 N52 C55 C56 -174.22(14) . . . . ?
Ni51 N52 C58 C57 -173.83(14) . . . . ?
Ni51 N52 C58 C59 4.7(3) . . . . ?
Ni51 N53 C60 O52 174.85(13) . . . . ?
Ni51 N53 C60 C59 -7.7(3) . . . . ?
Ni51 N53 C62 C61 -165.05(13) . . . . ?
Ni51 N53 C62 C63 72.29(19) . . . . ?
F51 Ni51 N51 C51 17.79(15) . . . . ?
F51 Ni51 N51 C53 -169.17(17) . . . . ?
F51 Ni51 N53 C60 -169.17(17) . . . . ?
F51 Ni51 N53 C62 13.41(15) . . . . ?
O51 C53 C54 C55 170.92(19) . . . . ?
O52 C61 C62 N53 -20.3(2) . . . . ?
O52 C61 C62 C63 99.0(2) . . . . ?
N51 Ni51 N52 C55 -10.84(17) . . . . ?
N51 Ni51 N52 C58 168.72(16) . . . . ?
N51 C51 C52 O51 -16.90(19) . . . . ?
N51 C51 C66 C67 62.2(2) . . . . ?
N51 C51 C66 C68 -172.67(15) . . . . ?
N51 C53 C54 C55 -5.5(3) . . . . ?
N52 Ni51 N51 C51 -163.46(15) . . . . ?
N52 Ni51 N51 C53 9.58(17) . . . . ?
N52 Ni51 N53 C60 12.08(17) . . . . ?
N52 Ni51 N53 C62 -165.33(15) . . . . ?
N52 C55 C56 C57 -15.0(2) . . . . ?
N52 C58 C59 C60 4.0(3) . . . . ?
N53 Ni51 N52 C55 169.99(16) . . . . ?
N53 Ni51 N52 C58 -10.46(16) . . . . ?
N53 C62 C63 C64 61.9(2) . . . . ?
N53 C62 C63 C65 -172.82(17) . . . . ?
C51 N51 C53 O51 -5.8(2) . . . . ?
C51 N51 C53 C54 170.65(19) . . . . ?
C52 O51 C53 N51 -5.9(2) . . . . ?
C52 O51 C53 C54 177.35(17) . . . . ?
C52 C51 C66 C67 -51.8(2) . . . . ?
C52 C51 C66 C68 73.3(2) . . . . ?
C53 O51 C52 C51 14.3(2) . . . . ?
C53 N51 C51 C52 13.96(19) . . . . ?
C53 N51 C51 C66 -108.11(18) . . . . ?
C53 C54 C55 N52 3.8(3) . . . . ?
C53 C54 C55 C56 -175.65(19) . . . . ?
C54 C55 C56 C57 164.5(2) . . . . ?
C55 N52 C58 C57 5.8(2) . . . . ?
C55 N52 C58 C59 -175.7(2) . . . . ?
C55 C56 C57 C58 17.0(2) . . . . ?
C56 C57 C58 N52 -14.9(2) . . . . ?
C56 C57 C58 C59 166.6(2) . . . . ?
C57 C58 C59 C60 -177.63(19) . . . . ?
C58 N52 C55 C54 -173.3(2) . . . . ?
C58 N52 C55 C56 6.2(2) . . . . ?
C58 C59 C60 O52 174.81(19) . . . . ?
C58 C59 C60 N53 -2.6(3) . . . . ?
C60 O52 C61 C62 17.0(2) . . . . ?
C60 N53 C62 C61 17.1(2) . . . . ?
C60 N53 C62 C63 -105.56(19) . . . . ?
C61 O52 C60 N53 -6.7(2) . . . . ?
C61 O52 C60 C59 175.63(18) . . . . ?
C61 C62 C63 C64 -52.4(3) . . . . ?
C61 C62 C63 C65 72.9(2) . . . . ?
C62 N53 C60 O52 -7.4(2) . . . . ?
C62 N53 C60 C59 170.10(19) . . . . ?
C66 C51 C52 O51 102.05(19) . . . . ?
C81 C82 C83 C84 1.9(4) . . . . ?
C82 C81 C86 C85 1.3(4) . . . . ?
C82 C83 C84 C85 -0.3(4) . . . . ?
C83 C84 C85 C86 -0.8(4) . . . . ?
C84 C85 C86 C81 0.3(4) . . . . ?
C86 C81 C82 C83 -2.4(4) . . . . ?
C87 C81 C82 C83 176.6(2) . . . . ?
C87 C81 C86 C85 -177.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

_diffrn_ambient_environment      'perfluoro polyether oil'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_specimen_support 'polyimid foil'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            CCD-PXL-KAF2
####################################################################### 
# 
# 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_ga_jw5_5
_database_code_depnum_ccdc_archive 'CCDC 1427464'
_audit_update_record             
;
2015-09-25 deposited with the CCDC.
2015-11-09 downloaded from the CCDC.
;
_audit_creation_date             2015-04-08

_audit_block_code                ga_jw5
_audit_block_refno               2396
_audit_block_usercomment         ?


_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C15 H12 F2'
_chemical_formula_sum            'C15 H12 F2'
_chemical_formula_weight         230.25
_chemical_melting_point          ?
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      100(1)
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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'C 2/c'
_symmetry_int_tables_number      15

_chemical_absolute_configuration .

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

_cell_length_a                   24.870(15)
_cell_length_b                   5.944(4)
_cell_length_c                   16.266(10)
_cell_angle_alpha                90
_cell_angle_beta                 107.995(7)
_cell_angle_gamma                90
_cell_volume                     2287(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.948
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.746416
_exptl_absorpt_correction_T_min  0.651067

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements (Blessing 1995)
SADABS (see _computing_data_reduction)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.130
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            34259
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.431
_diffrn_reflns_theta_min         1.722
_diffrn_detector_area_resol_mean 8.19
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  'Bruker AXS Smart 1000'
_diffrn_measurement_method       'φ- and ω-scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-Ray tube (Mo)'
_diffrn_source_type              'fine focus tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4459
_reflns_number_total             5453
_reflns_special_details          
;
 _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 (see _computing_data_reduction). Includes estimated systematic errors
 of the unit cell constants from Monte Carlo simulations.
;
_computing_data_collection       'SMART-5.631 (Bruker AXS, 2003)'
_computing_data_reduction        
'SAINT V8.34A (Bruker AXS, 1997-2013),SADABS (Sheldrick and Bruker AXS, 1997-2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  
'encif (Wadepohl, 2009-14); encifer 1.5 (CCDC, 2014)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_shelxl_version_number           2014/7
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007-2009)'
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         5453
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      1.067
_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)+(0.0625P)²+0.7491P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1185
_refine_special_details          
;
 Refined as a 2-component twin against all singles and composites from both domains.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.3374(11) 0.6626(11)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
F1 F 0.44167(4) -0.22197(15) 0.41896(6) 0.0242(2) Uani 1 1 d . . . . .
F2 F 0.48616(4) -0.10650(15) 0.33019(6) 0.0250(2) Uani 1 1 d . . . . .
C10 C 0.34718(5) 0.0765(2) 0.34693(8) 0.0127(2) Uani 1 1 d . . . . .
C4 C 0.39893(5) 0.1952(2) 0.24132(9) 0.0133(2) Uani 1 1 d . . . . .
C1 C 0.40233(5) 0.1110(2) 0.32977(8) 0.0129(2) Uani 1 1 d . . . . .
C11 C 0.32371(6) 0.2503(2) 0.38204(9) 0.0161(3) Uani 1 1 d . . . . .
H11 H 0.3430(7) 0.390(3) 0.3975(11) 0.019 Uiso 1 1 d R . . . .
C2 C 0.45003(6) -0.0425(2) 0.37272(10) 0.0178(3) Uani 1 1 d . . . . .
C15 C 0.31741(6) -0.1252(2) 0.32584(9) 0.0163(3) Uani 1 1 d . . . . .
H15 H 0.3337(7) -0.247(3) 0.3007(12) 0.020 Uiso 1 1 d R . . . .
C9 C 0.37336(6) 0.0617(2) 0.16939(9) 0.0172(3) Uani 1 1 d . . . . .
H9 H 0.3577(8) -0.084(3) 0.1771(11) 0.021 Uiso 1 1 d R . . . .
C5 C 0.42045(6) 0.4040(2) 0.22863(10) 0.0182(3) Uani 1 1 d . . . . .
H5 H 0.4377(10) 0.494(2) 0.2790(14) 0.022 Uiso 1 1 d R . . . .
C12 C 0.27189(6) 0.2230(3) 0.39640(10) 0.0210(3) Uani 1 1 d . . . . .
H12 H 0.2563(8) 0.343(3) 0.4216(12) 0.025 Uiso 1 1 d R . . . .
C3 C 0.45329(6) 0.1852(3) 0.40803(10) 0.0200(3) Uani 1 1 d . . . . .
H3A H 0.4809(8) 0.279(3) 0.3988(11) 0.024 Uiso 1 1 d R . . . .
H3B H 0.4453(8) 0.206(3) 0.4589(12) 0.024 Uiso 1 1 d R . . . .
C14 C 0.26542(6) -0.1515(2) 0.33958(10) 0.0209(3) Uani 1 1 d . . . . .
H14 H 0.2448(8) -0.289(3) 0.3266(12) 0.025 Uiso 1 1 d R . . . .
C6 C 0.41690(7) 0.4768(2) 0.14612(12) 0.0224(3) Uani 1 1 d . . . . .
H6 H 0.4314(8) 0.618(3) 0.1364(12) 0.027 Uiso 1 1 d R . . . .
C8 C 0.36986(7) 0.1339(3) 0.08693(10) 0.0221(3) Uani 1 1 d . . . . .
H8 H 0.3522(10) 0.036(3) 0.0368(14) 0.027 Uiso 1 1 d R . . . .
C13 C 0.24262(7) 0.0218(3) 0.37517(11) 0.0231(3) Uani 1 1 d . . . . .
H13 H 0.2083(11) 0.000(3) 0.3845(15) 0.028 Uiso 1 1 d R . . . .
C7 C 0.39204(7) 0.3417(3) 0.07540(11) 0.0239(3) Uani 1 1 d . . . . .
H7 H 0.3888(8) 0.389(3) 0.0182(12) 0.029 Uiso 1 1 d 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 C2 1.3579(18) . ?
F2 C2 1.3472(18) . ?
C10 C1 1.496(2) . ?
C10 C11 1.3928(19) . ?
C10 C15 1.3949(19) . ?
C4 C1 1.501(2) . ?
C4 C9 1.394(2) . ?
C4 C5 1.3923(19) . ?
C1 C2 1.488(2) . ?
C1 C3 1.557(2) . ?
C11 H11 0.952(18) . ?
C11 C12 1.388(2) . ?
C2 C3 1.462(2) . ?
C15 H15 0.979(17) . ?
C15 C14 1.388(2) . ?
C9 H9 0.974(19) . ?
C9 C8 1.385(2) . ?
C5 H5 0.96(2) . ?
C5 C6 1.387(2) . ?
C12 H12 0.960(18) . ?
C12 C13 1.387(2) . ?
C3 H3A 0.933(19) . ?
C3 H3B 0.917(19) . ?
C14 H14 0.955(18) . ?
C14 C13 1.386(2) . ?
C6 H6 0.947(19) . ?
C6 C7 1.382(3) . ?
C8 H8 0.99(2) . ?
C8 C7 1.389(2) . ?
C13 H13 0.92(2) . ?
C7 H7 0.952(18) . ?

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
C11 C10 C1 119.94(12) . . ?
C11 C10 C15 118.72(13) . . ?
C15 C10 C1 121.31(12) . . ?
C9 C4 C1 119.40(12) . . ?
C5 C4 C1 121.92(12) . . ?
C5 C4 C9 118.67(13) . . ?
C10 C1 C4 116.18(11) . . ?
C10 C1 C3 116.62(12) . . ?
C4 C1 C3 118.69(11) . . ?
C2 C1 C10 118.16(12) . . ?
C2 C1 C4 117.06(11) . . ?
C2 C1 C3 57.34(10) . . ?
C10 C11 H11 120.9(10) . . ?
C12 C11 C10 120.70(13) . . ?
C12 C11 H11 118.4(10) . . ?
F1 C2 C1 120.37(13) . . ?
F1 C2 C3 120.59(13) . . ?
F2 C2 F1 107.63(12) . . ?
F2 C2 C1 119.57(13) . . ?
F2 C2 C3 119.88(13) . . ?
C3 C2 C1 63.68(10) . . ?
C10 C15 H15 118.8(10) . . ?
C14 C15 C10 120.49(13) . . ?
C14 C15 H15 120.7(10) . . ?
C4 C9 H9 119.7(10) . . ?
C8 C9 C4 120.82(14) . . ?
C8 C9 H9 119.5(10) . . ?
C4 C5 H5 117.3(11) . . ?
C6 C5 C4 120.60(14) . . ?
C6 C5 H5 122.1(11) . . ?
C11 C12 H12 120.2(11) . . ?
C13 C12 C11 120.13(14) . . ?
C13 C12 H12 119.6(11) . . ?
C1 C3 H3A 119.5(11) . . ?
C1 C3 H3B 115.3(12) . . ?
C2 C3 C1 58.98(9) . . ?
C2 C3 H3A 116.5(11) . . ?
C2 C3 H3B 118.5(11) . . ?
H3A C3 H3B 116.0(16) . . ?
C15 C14 H14 121.6(11) . . ?
C13 C14 C15 120.35(14) . . ?
C13 C14 H14 118.0(11) . . ?
C5 C6 H6 121.6(12) . . ?
C7 C6 C5 120.17(14) . . ?
C7 C6 H6 118.2(12) . . ?
C9 C8 H8 119.7(11) . . ?
C9 C8 C7 119.83(15) . . ?
C7 C8 H8 120.4(11) . . ?
C12 C13 H13 121.5(11) . . ?
C14 C13 C12 119.60(15) . . ?
C14 C13 H13 118.9(11) . . ?
C6 C7 C8 119.91(15) . . ?
C6 C7 H7 121.4(12) . . ?
C8 C7 H7 118.7(12) . . ?

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
F1 C2 C3 C1 -111.27(15) . . . . ?
F2 C2 C3 C1 110.53(15) . . . . ?
C10 C1 C2 F1 6.51(19) . . . . ?
C10 C1 C2 F2 143.90(13) . . . . ?
C10 C1 C2 C3 -105.10(14) . . . . ?
C10 C1 C3 C2 107.80(13) . . . . ?
C10 C11 C12 C13 -0.5(2) . . . . ?
C10 C15 C14 C13 -0.6(2) . . . . ?
C4 C1 C2 F1 -140.16(13) . . . . ?
C4 C1 C2 F2 -2.77(19) . . . . ?
C4 C1 C2 C3 108.23(13) . . . . ?
C4 C1 C3 C2 -105.38(14) . . . . ?
C4 C9 C8 C7 0.0(2) . . . . ?
C4 C5 C6 C7 -0.2(2) . . . . ?
C1 C10 C11 C12 178.40(12) . . . . ?
C1 C10 C15 C14 -177.84(13) . . . . ?
C1 C4 C9 C8 -179.60(12) . . . . ?
C1 C4 C5 C6 179.72(13) . . . . ?
C11 C10 C1 C4 -91.41(15) . . . . ?
C11 C10 C1 C2 121.64(14) . . . . ?
C11 C10 C1 C3 56.25(16) . . . . ?
C11 C10 C15 C14 0.1(2) . . . . ?
C11 C12 C13 C14 0.0(2) . . . . ?
C15 C10 C1 C4 86.48(15) . . . . ?
C15 C10 C1 C2 -60.47(18) . . . . ?
C15 C10 C1 C3 -125.87(14) . . . . ?
C15 C10 C11 C12 0.46(19) . . . . ?
C15 C14 C13 C12 0.5(2) . . . . ?
C9 C4 C1 C10 -63.80(16) . . . . ?
C9 C4 C1 C2 83.52(16) . . . . ?
C9 C4 C1 C3 149.24(13) . . . . ?
C9 C4 C5 C6 -0.5(2) . . . . ?
C9 C8 C7 C6 -0.8(2) . . . . ?
C5 C4 C1 C10 115.95(14) . . . . ?
C5 C4 C1 C2 -96.73(15) . . . . ?
C5 C4 C1 C3 -31.00(18) . . . . ?
C5 C4 C9 C8 0.6(2) . . . . ?
C5 C6 C7 C8 0.9(2) . . . . ?
C3 C1 C2 F1 111.61(16) . . . . ?
C3 C1 C2 F2 -111.00(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.3374(11)
2 0.6626(11)

_diffrn_ambient_environment      'perfluoro polyether oil / N~2~'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_specimen_support 'polyimid foil'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            CCD-PXL-KAF2



####################################################################### 
# 
# 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_ga_jw4
_database_code_depnum_ccdc_archive 'CCDC 1427465'
_audit_update_record             
;
2015-09-25 deposited with the CCDC.
2015-11-09 downloaded from the CCDC.
;
_audit_creation_date             
;
'Tue Mar 10 13:40:16 2015'
;

_audit_block_code                ga_jw4
_audit_block_refno               2364
_audit_block_usercomment         'JWAA60, irregular, colourless'


_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C15 H13 F'
_chemical_formula_sum            'C15 H13 F'
_chemical_formula_weight         212.25
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'C c'
_symmetry_int_tables_number      9
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      120(1)
_chemical_oxdiff_formula         'C15 H13 F'
_chemical_oxdiff_usercomment     'JWAA60, irregular, colourless'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 '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           9
_space_group_name_H-M_alt        'C 1 c 1'

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

_cell_length_a                   7.74284(13)
_cell_length_b                   17.2689(2)
_cell_length_c                   8.39473(13)
_cell_angle_alpha                90
_cell_angle_beta                 91.1751(15)
_cell_angle_gamma                90
_cell_volume                     1122.23(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12699
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      70.6640
_cell_measurement_theta_min      5.1250
_shelx_estimated_absorpt_T_max   0.937
_shelx_estimated_absorpt_T_min   0.937
_exptl_absorpt_coefficient_mu    0.661
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.937
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.158
_exptl_crystal_size_mid          0.079
_exptl_crystal_size_min          0.033
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            20879
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.780
_diffrn_reflns_theta_min         5.122
_diffrn_ambient_environment      'perfluoro polyether oil / N~2~'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9621
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -20.00   14.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000  -30.0000 34

#__ type_ start__ end____ width___ exp.time_
  2 omega   33.00   61.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000  120.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega  -28.00    9.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000  120.0000 37

#__ type_ start__ end____ width___ exp.time_
  4 omega  -68.00  -43.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
  5 omega   26.00   53.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega  -17.00   21.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  120.0000 38

#__ type_ start__ end____ width___ exp.time_
  7 omega   -2.00   23.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   80.0000  -11.0389 25

#__ type_ start__ end____ width___ exp.time_
  8 omega    5.00   32.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   69.0000  141.7096 27

#__ type_ start__ end____ width___ exp.time_
  9 omega    7.00   32.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   78.0000 -135.5313 25

#__ type_ start__ end____ width___ exp.time_
 10 omega   11.00   38.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   79.0000  165.7183 27

#__ type_ start__ end____ width___ exp.time_
 11 omega   13.00   40.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   75.0000   48.2451 27

#__ type_ start__ end____ width___ exp.time_
 12 omega   70.00  112.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   75.0000   48.2451 42

#__ type_ start__ end____ width___ exp.time_
 13 omega   16.00   45.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   79.0000  -48.9570 29

#__ type_ start__ end____ width___ exp.time_
 14 omega   19.00   46.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   78.0000 -112.1569 27

#__ type_ start__ end____ width___ exp.time_
 15 omega  -14.00   83.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000   90.0000 97

#__ type_ start__ end____ width___ exp.time_
 16 omega   25.00   50.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 17 omega  -16.00   27.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000    0.0000 43

#__ type_ start__ end____ width___ exp.time_
 18 omega   25.00   52.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
 19 omega   24.00   51.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 20 omega   25.00   52.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 21 omega  -12.00   85.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -80.0000  -75.6100 97

#__ type_ start__ end____ width___ exp.time_
 22 omega   91.00  120.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   30.0000 29

#__ type_ start__ end____ width___ exp.time_
 23 omega   32.00   81.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000    0.0000 49

#__ type_ start__ end____ width___ exp.time_
 24 omega  -16.00   76.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000 -180.0000 92

#__ type_ start__ end____ width___ exp.time_
 25 omega   25.00   52.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
 26 omega   28.00   55.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 27 omega   25.00   54.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
 28 omega   34.00   64.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -150.0000 30

#__ type_ start__ end____ width___ exp.time_
 29 omega   36.00   63.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   75.0000   -2.4890 27

#__ type_ start__ end____ width___ exp.time_
 30 omega   56.00   83.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   58.0000  -60.7934 27

#__ type_ start__ end____ width___ exp.time_
 31 omega   80.00  113.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   73.0000 -152.6063 33

#__ type_ start__ end____ width___ exp.time_
 32 omega   31.00   64.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   73.0000 -141.6068 33

#__ type_ start__ end____ width___ exp.time_
 33 omega   31.00   58.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   73.0000 -152.6063 27

#__ type_ start__ end____ width___ exp.time_
 34 omega   53.00   80.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   51.0000  117.0057 27

#__ type_ start__ end____ width___ exp.time_
 35 omega   38.00   65.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   76.0000  127.7226 27

#__ type_ start__ end____ width___ exp.time_
 36 omega   38.00   64.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   76.0000 -101.3588 26

#__ type_ start__ end____ width___ exp.time_
 37 omega   39.00   77.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   72.0000  -17.2532 38

#__ type_ start__ end____ width___ exp.time_
 38 omega   51.00  111.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   40.0000  145.3008 60

#__ type_ start__ end____ width___ exp.time_
 39 omega   51.00   89.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   58.0000  -87.7198 38

#__ type_ start__ end____ width___ exp.time_
 40 omega   46.00   99.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   71.0000  156.9396 53

#__ type_ start__ end____ width___ exp.time_
 41 omega   41.00   74.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   75.0000   22.7668 33

#__ type_ start__ end____ width___ exp.time_
 42 omega   58.00   84.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   60.0000   61.6781 26

#__ type_ start__ end____ width___ exp.time_
 43 omega   65.00   92.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   51.0000   91.9608 27

#__ type_ start__ end____ width___ exp.time_
 44 omega   56.00  112.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   63.0000  -60.7604 56

#__ type_ start__ end____ width___ exp.time_
 45 omega   57.00   93.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   52.0000  -57.7986 36

#__ type_ start__ end____ width___ exp.time_
 46 omega   52.00   78.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   77.0000  108.1101 26

#__ type_ start__ end____ width___ exp.time_
 47 omega   57.00  107.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       86.0000   77.0000  -45.8553 50

#__ type_ start__ end____ width___ exp.time_
 48 omega   68.00  117.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       86.0000   57.0000   10.0889 49

#__ type_ start__ end____ width___ exp.time_
 49 omega   64.00   92.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       86.0000   66.0000  178.0174 28

#__ type_ start__ end____ width___ exp.time_
 50 omega  112.00  140.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       90.0000   53.0000 -160.9567 28

#__ type_ start__ end____ width___ exp.time_
 51 omega   76.00  106.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       90.0000   53.0000 -160.9567 30

#__ type_ start__ end____ width___ exp.time_
 52 omega   76.00  102.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       98.0000   67.0000  154.9102 26

#__ type_ start__ end____ width___ exp.time_
 53 omega   83.00  111.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 28

#__ type_ start__ end____ width___ exp.time_
 54 omega   80.00  107.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 55 omega   78.00  163.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 85

#__ type_ start__ end____ width___ exp.time_
 56 omega  136.00  162.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 57 omega   79.00  129.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 50

#__ type_ start__ end____ width___ exp.time_
 58 omega   80.00  106.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 59 omega   86.00  175.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000  -90.0000 89

#__ type_ start__ end____ width___ exp.time_
 60 omega   79.00  163.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 84

#__ type_ start__ end____ width___ exp.time_
 61 omega   85.00  174.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000  -30.0000 89

#__ type_ start__ end____ width___ exp.time_
 62 omega  116.00  177.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 61

#__ type_ start__ end____ width___ exp.time_
 63 omega   86.00  175.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000  120.0000 89

#__ type_ start__ end____ width___ exp.time_
 64 omega   56.00  101.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -30.0000 45

#__ type_ start__ end____ width___ exp.time_
 65 omega   87.00  114.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 66 omega   78.00  177.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 99

#__ type_ start__ end____ width___ exp.time_
 67 omega   85.00  135.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000 -120.0000 50

#__ type_ start__ end____ width___ exp.time_
 68 omega  134.00  170.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000 -150.0000 36

#__ type_ start__ end____ width___ exp.time_
 69 omega   86.00  129.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000 -150.0000 43

#__ type_ start__ end____ width___ exp.time_
 70 omega   86.00  111.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 71 omega   66.00   94.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   30.0000 28

#__ type_ start__ end____ width___ exp.time_
 72 omega   90.00  115.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 73 omega   38.00  139.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -79.0000  -63.8358 101

#__ type_ start__ end____ width___ exp.time_
 74 omega   79.00  104.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 75 omega   87.00  112.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 76 omega   65.00   92.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 77 omega   38.00   64.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 78 omega   86.00  157.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000 -120.0000 71

#__ type_ start__ end____ width___ exp.time_
 79 omega  110.00  137.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
 80 omega   44.00  104.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -150.0000 60

#__ type_ start__ end____ width___ exp.time_
 81 omega   88.00  115.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 82 omega   87.00  164.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000   90.0000 77

#__ type_ start__ end____ width___ exp.time_
 83 omega   37.00  138.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -79.0000   89.8360 101

#__ type_ start__ end____ width___ exp.time_
 84 omega   82.00  110.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  -60.0000 28

#__ type_ start__ end____ width___ exp.time_
 85 omega  117.00  160.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 43

#__ type_ start__ end____ width___ exp.time_
 86 omega   84.00  110.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 87 omega   79.00  106.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 88 omega   63.00   90.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -78.0000  177.2337 27

#__ type_ start__ end____ width___ exp.time_
 89 omega  -44.00   73.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   19.0000 -150.0000 117

#__ type_ start__ end____ width___ exp.time_
 90 omega  -11.00   88.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0000   75.0000  -15.0189 99

#__ type_ start__ end____ width___ exp.time_
 91 omega   -3.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       22.0000   69.0000   37.0363 93

#__ type_ start__ end____ width___ exp.time_
 92 omega   -9.00   47.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       22.0000   79.0000 -156.4420 56

#__ type_ start__ end____ width___ exp.time_
 93 omega   15.00   47.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   79.0000  -48.9570 32

#__ type_ start__ end____ width___ exp.time_
 94 phi      0.00  120.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
  54.0000   54.0000   40.0000     -     120

#__ type_ start__ end____ width___ exp.time_
 95 omega   24.00  124.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  120.0000 100

#__ type_ start__ end____ width___ exp.time_
 96 phi      0.00  120.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
  40.0000   54.0000    0.0000     -     120

#__ type_ start__ end____ width___ exp.time_
 97 phi      0.00  120.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
  54.0000   54.0000   20.0000     -     120

#__ type_ start__ end____ width___ exp.time_
 98 omega  -19.00  127.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000    0.0000  120.0000 146

#__ type_ start__ end____ width___ exp.time_
 99 omega  -19.00  127.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000    0.0000    0.0000 146

#__ type_ start__ end____ width___ exp.time_
100 omega  -19.00  127.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000    0.0000  120.0000 146

#__ type_ start__ end____ width___ exp.time_
101 omega  -16.00   84.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000  -60.0000 100

#__ type_ start__ end____ width___ exp.time_
102 omega  -16.00   84.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000  120.0000 100

#__ type_ start__ end____ width___ exp.time_
103 omega  -19.00  127.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000    0.0000  240.0000 146

#__ type_ start__ end____ width___ exp.time_
104 phi      0.00  120.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
  54.0000   54.0000  -60.0000     -     120

#__ type_ start__ end____ width___ exp.time_
105 phi      0.00  120.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
  54.0000   54.0000  -40.0000     -     120

#__ type_ start__ end____ width___ exp.time_
106 phi      0.00  120.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
  54.0000   54.0000  -20.0000     -     120

#__ type_ start__ end____ width___ exp.time_
107 omega   24.00  124.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   90.0000 100

#__ type_ start__ end____ width___ exp.time_
108 omega  -15.00   75.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000 -180.0000 90

#__ type_ start__ end____ width___ exp.time_
109 omega   24.00  124.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  -30.0000 100

#__ type_ start__ end____ width___ exp.time_
110 omega  -16.00   84.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000   60.0000 100

#__ type_ start__ end____ width___ exp.time_
111 omega  -19.00  127.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000    0.0000  240.0000 146

#__ type_ start__ end____ width___ exp.time_
112 omega  -19.00  127.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000    0.0000    0.0000 146

#__ type_ start__ end____ width___ exp.time_
113 omega   30.00  127.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   73.0000 -152.6063 97

#__ type_ start__ end____ width___ exp.time_
114 omega   30.00  127.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   73.0000 -141.6068 97

#__ type_ start__ end____ width___ exp.time_
115 omega   39.00  135.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   72.0000  -17.2532 96

#__ type_ start__ end____ width___ exp.time_
116 omega   37.00  136.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   76.0000 -101.3588 99

#__ type_ start__ end____ width___ exp.time_
117 omega   37.00  136.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   76.0000  127.7226 99

#__ type_ start__ end____ width___ exp.time_
118 omega   41.00  140.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   75.0000   22.7668 99

#__ type_ start__ end____ width___ exp.time_
119 omega   43.00  139.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   71.0000  156.9396 96

#__ type_ start__ end____ width___ exp.time_
120 omega   49.00  139.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   58.0000  -87.7198 90

#__ type_ start__ end____ width___ exp.time_
121 omega   52.00  144.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   50.0000   94.4446 92

#__ type_ start__ end____ width___ exp.time_
122 omega   56.00  146.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   63.0000  -60.7604 90

#__ type_ start__ end____ width___ exp.time_
123 omega   57.00  148.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   52.0000  -57.7986 91

#__ type_ start__ end____ width___ exp.time_
124 omega   57.00  146.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   60.0000   61.6781 89

#__ type_ start__ end____ width___ exp.time_
125 omega   78.00  167.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 89

#__ type_ start__ end____ width___ exp.time_
126 omega   86.00  178.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -30.0000 92

#__ type_ start__ end____ width___ exp.time_
127 omega   85.00  175.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000 -120.0000 90

#__ type_ start__ end____ width___ exp.time_
128 omega   86.00  178.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000   60.0000 92

#__ type_ start__ end____ width___ exp.time_
129 omega   38.00  104.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  -30.0000 66

#__ type_ start__ end____ width___ exp.time_
130 omega   74.00  178.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000 -180.0000 104

#__ type_ start__ end____ width___ exp.time_
131 omega   38.00  138.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -120.0000 100

#__ type_ start__ end____ width___ exp.time_
132 omega   35.00   94.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  120.0000 59

#__ type_ start__ end____ width___ exp.time_
133 omega   35.00   94.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000    0.0000 59

#__ type_ start__ end____ width___ exp.time_
134 omega   35.00   94.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -120.0000 59

#__ type_ start__ end____ width___ exp.time_
135 omega   36.00   93.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -120.0000 57

#__ type_ start__ end____ width___ exp.time_
136 omega   37.00  139.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -79.0000   89.8360 102

;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω and π scans'
_diffrn_orient_matrix_UB_11      -0.0207962000
_diffrn_orient_matrix_UB_12      -0.0874593000
_diffrn_orient_matrix_UB_13      0.0304183000
_diffrn_orient_matrix_UB_21      -0.0991557000
_diffrn_orient_matrix_UB_22      -0.0084393000
_diffrn_orient_matrix_UB_23      -0.1600785000
_diffrn_orient_matrix_UB_31      0.1712489000
_diffrn_orient_matrix_UB_32      -0.0154856000
_diffrn_orient_matrix_UB_33      -0.0845373000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'microfocus X-Ray tube'
_diffrn_source_type              'Agilent SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.895
_reflns_Friedel_fraction_full    0.906
_reflns_Friedel_fraction_max     0.893
_reflns_number_gt                2020
_reflns_number_total             2047
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  
'encif (Wadepohl, 2009-14); encifer 1.5 (CCDC, 2014)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_shelxl_version_number           2014/7
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007-2009)'
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 
;
 Flack x determined using 928 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2047
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0255
_refine_ls_restrained_S_all      1.079
_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)+(0.0362P)²+0.2792P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0654
_refine_ls_wR_factor_ref         0.0656
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group with stretchable bonds:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
F F 0.15004(16) 0.15976(6) 0.41077(14) 0.0317(3) Uani 1 1 d . . . . .
C1 C 0.4891(2) 0.31120(10) 0.4252(2) 0.0214(4) Uani 1 1 d . . . . .
C2 C 0.2268(3) 0.23136(10) 0.4112(2) 0.0238(4) Uani 1 1 d . . . . .
C3 C 0.5089(2) 0.16481(10) 0.3934(2) 0.0213(4) Uani 1 1 d . . . . .
C4 C 0.6610(3) 0.15693(10) 0.4842(2) 0.0245(4) Uani 1 1 d . . . . .
H4 H 0.692(3) 0.1970(14) 0.560(3) 0.029 Uiso 1 1 d R . . . .
C5 C 0.3982(2) 0.23498(10) 0.4103(2) 0.0221(4) Uani 1 1 d . . . . .
C6 C 0.4621(3) 0.36040(11) 0.5538(2) 0.0243(4) Uani 1 1 d . . . . .
H6 H 0.385(3) 0.3459(13) 0.636(3) 0.029 Uiso 1 1 d R . . . .
C7 C 0.6669(3) 0.45178(11) 0.4517(2) 0.0282(4) Uani 1 1 d . . . . .
H7 H 0.726(3) 0.5000(15) 0.462(3) 0.034 Uiso 1 1 d R . . . .
C8 C 0.7650(3) 0.09171(11) 0.4694(2) 0.0280(4) Uani 1 1 d . . . . .
H8 H 0.870(3) 0.0873(14) 0.535(3) 0.034 Uiso 1 1 d R . . . .
C9 C 0.4665(3) 0.10669(10) 0.2829(2) 0.0246(4) Uani 1 1 d . . . . .
H9 H 0.370(3) 0.1138(13) 0.220(3) 0.030 Uiso 1 1 d R . . . .
C10 C 0.5505(3) 0.43005(11) 0.5666(2) 0.0278(4) Uani 1 1 d . . . . .
H10 H 0.532(3) 0.4634(13) 0.659(3) 0.033 Uiso 1 1 d R . . . .
C11 C 0.6961(3) 0.40275(11) 0.3241(2) 0.0289(4) Uani 1 1 d . . . . .
H11 H 0.779(3) 0.4183(15) 0.242(3) 0.035 Uiso 1 1 d R . . . .
C12 C 0.6090(3) 0.33264(11) 0.3123(2) 0.0263(4) Uani 1 1 d . . . . .
H12 H 0.630(3) 0.2969(14) 0.219(3) 0.032 Uiso 1 1 d R . . . .
C13 C 0.7198(3) 0.03383(11) 0.3607(2) 0.0292(4) Uani 1 1 d . . . . .
H13 H 0.795(3) -0.0115(15) 0.356(3) 0.035 Uiso 1 1 d R . . . .
C14 C 0.5718(3) 0.04234(11) 0.2667(2) 0.0287(4) Uani 1 1 d . . . . .
H14 H 0.542(4) 0.0032(14) 0.195(3) 0.034 Uiso 1 1 d R . . . .
C15 C 0.0935(3) 0.29299(12) 0.4109(2) 0.0297(4) Uani 1 1 d . . . . .
H15A H 0.0107(19) 0.2845(6) 0.3202(18) 0.045 Uiso 1 1 calc GR . . . .
H15B H 0.1501(9) 0.3444(8) 0.399(2) 0.045 Uiso 1 1 calc GR . . . .
H15C H 0.0303(17) 0.2914(6) 0.5130(19) 0.045 Uiso 1 1 calc GR . . . .


_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
F C2 1.372(2) . ?
C1 C5 1.497(2) . ?
C1 C6 1.393(3) . ?
C1 C12 1.391(3) . ?
C2 C5 1.329(3) . ?
C2 C15 1.482(3) . ?
C3 C4 1.396(3) . ?
C3 C5 1.493(3) . ?
C3 C9 1.401(2) . ?
C4 H4 0.97(2) . ?
C4 C8 1.392(3) . ?
C6 H6 0.95(3) . ?
C6 C10 1.387(3) . ?
C7 H7 0.96(3) . ?
C7 C10 1.385(3) . ?
C7 C11 1.388(3) . ?
C8 H8 0.97(3) . ?
C8 C13 1.394(3) . ?
C9 H9 0.91(2) . ?
C9 C14 1.387(3) . ?
C10 H10 0.98(3) . ?
C11 H11 0.99(3) . ?
C11 C12 1.388(3) . ?
C12 H12 1.01(3) . ?
C13 H13 0.98(3) . ?
C13 C14 1.386(3) . ?
C14 H14 0.93(2) . ?
C15 H15A 0.996(16) . ?
C15 H15B 0.996(16) . ?
C15 H15C 0.996(16) . ?

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
C6 C1 C5 121.54(16) . . ?
C12 C1 C5 119.79(15) . . ?
C12 C1 C6 118.62(16) . . ?
F C2 C15 110.20(17) . . ?
C5 C2 F 118.38(16) . . ?
C5 C2 C15 131.42(17) . . ?
C4 C3 C5 120.43(16) . . ?
C4 C3 C9 118.38(17) . . ?
C9 C3 C5 121.15(17) . . ?
C3 C4 H4 119.1(14) . . ?
C8 C4 C3 120.89(17) . . ?
C8 C4 H4 120.0(14) . . ?
C2 C5 C1 120.60(16) . . ?
C2 C5 C3 122.53(16) . . ?
C3 C5 C1 116.87(16) . . ?
C1 C6 H6 120.3(14) . . ?
C10 C6 C1 120.47(19) . . ?
C10 C6 H6 119.2(14) . . ?
C10 C7 H7 119.3(16) . . ?
C10 C7 C11 119.41(18) . . ?
C11 C7 H7 121.2(16) . . ?
C4 C8 H8 119.5(15) . . ?
C4 C8 C13 120.06(19) . . ?
C13 C8 H8 120.5(15) . . ?
C3 C9 H9 117.6(15) . . ?
C14 C9 C3 120.57(18) . . ?
C14 C9 H9 121.8(15) . . ?
C6 C10 H10 119.6(15) . . ?
C7 C10 C6 120.54(17) . . ?
C7 C10 H10 119.9(15) . . ?
C7 C11 H11 119.5(14) . . ?
C7 C11 C12 120.0(2) . . ?
C12 C11 H11 120.5(14) . . ?
C1 C12 H12 119.1(14) . . ?
C11 C12 C1 120.90(18) . . ?
C11 C12 H12 120.0(14) . . ?
C8 C13 H13 117.6(14) . . ?
C14 C13 C8 119.38(19) . . ?
C14 C13 H13 123.0(14) . . ?
C9 C14 H14 120.6(16) . . ?
C13 C14 C9 120.67(18) . . ?
C13 C14 H14 118.7(16) . . ?
C2 C15 H15A 109.5 . . ?
C2 C15 H15B 109.5 . . ?
C2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
F C2 C5 C1 -174.61(15) . . . . ?
F C2 C5 C3 5.9(2) . . . . ?
C1 C6 C10 C7 0.0(3) . . . . ?
C3 C4 C8 C13 1.3(3) . . . . ?
C3 C9 C14 C13 0.7(3) . . . . ?
C4 C3 C5 C1 41.2(2) . . . . ?
C4 C3 C5 C2 -139.32(18) . . . . ?
C4 C3 C9 C14 1.2(3) . . . . ?
C4 C8 C13 C14 0.7(3) . . . . ?
C5 C1 C6 C10 178.72(17) . . . . ?
C5 C1 C12 C11 -179.49(17) . . . . ?
C5 C3 C4 C8 179.92(18) . . . . ?
C5 C3 C9 C14 179.04(17) . . . . ?
C6 C1 C5 C2 56.2(2) . . . . ?
C6 C1 C5 C3 -124.27(18) . . . . ?
C6 C1 C12 C11 -2.1(3) . . . . ?
C7 C11 C12 C1 1.4(3) . . . . ?
C8 C13 C14 C9 -1.7(3) . . . . ?
C9 C3 C4 C8 -2.2(3) . . . . ?
C9 C3 C5 C1 -136.60(17) . . . . ?
C9 C3 C5 C2 42.9(3) . . . . ?
C10 C7 C11 C12 0.0(3) . . . . ?
C11 C7 C10 C6 -0.7(3) . . . . ?
C12 C1 C5 C2 -126.48(19) . . . . ?
C12 C1 C5 C3 53.0(2) . . . . ?
C12 C1 C6 C10 1.4(3) . . . . ?
C15 C2 C5 C1 6.2(3) . . . . ?
C15 C2 C5 C3 -173.28(18) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4 2 3 0.0554 -4.0035 2.0010 3.0005 -0.0005 -0.1002 -0.9702
1 3 5 0.0523 0.9958 2.9994 5.0004 -0.1309 -0.9245 -0.2986
4 -2 -3 0.0144 4.0035 -2.0010 -3.0005 0.0005 0.1002 0.9702
-4 6 2 0.0542 -4.0035 6.0007 2.0003 -0.3807 0.0261 -0.9476
2 10 -1 0.0159 1.9993 9.9986 -1.0006 -0.9465 -0.1225 0.2721
-2 -10 1 0.0170 -1.9993 -9.9986 1.0006 0.9465 0.1225 -0.2721
-5 -1 -2 0.0573 -4.9993 -0.9984 -1.9998 0.1305 0.8243 -0.6716

_olex2_submission_special_instructions 'No special instructions were received'
_cell_oxdiff_length_a            7.7443(2)
_cell_oxdiff_length_b            17.2671(4)
_cell_oxdiff_length_c            8.3942(2)
_cell_oxdiff_angle_alpha         89.9986(19)
_cell_oxdiff_angle_beta          91.197(2)
_cell_oxdiff_angle_gamma         90.012(2)
_cell_oxdiff_volume              1122.23(5)
_cell_oxdiff_measurement_reflns_used 12705
_diffrn_measurement_specimen_support 'polyimid foil'


#==end==

