# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_nicamtfe2
_database_code_depnum_ccdc_archive 'CCDC 1430237'
_audit_update_record             
;
2015-10-08 deposited with the CCDC.
2015-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H26 Cl2 F6 N4 Ni'
_chemical_formula_sum            'C14 H26 Cl2 F6 N4 Ni'
_chemical_formula_weight         494.00
_chemical_compound_source        'synthesized by the authors'

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_space_group_name_H-M_alt        'C 1 2/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'
'-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                   22.2787(9)
_cell_length_b                   6.4382(3)
_cell_length_c                   16.0685(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 122.8520(10)
_cell_angle_gamma                90.00
_cell_volume                     1936.19(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5699
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      27.48

_exptl_crystal_description       prism
_exptl_crystal_colour            blue-green
_exptl_crystal_size_max          0.259
_exptl_crystal_size_mid          0.223
_exptl_crystal_size_min          0.108
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016
_exptl_absorpt_coefficient_mu    1.341
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_T_max  0.79
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13393
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         27.49
_reflns_number_total             2232
_reflns_number_gt                1973
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0401P)²+8.7750P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2232
_refine_ls_number_parameters     133
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.0984
_refine_ls_wR_factor_gt          0.0951
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 1.0000 0.49089(7) 0.2500 0.01213(14) Uani 1 2 d S . .
Cl1 Cl 0.97518(3) 0.76035(9) 0.13049(5) 0.01890(16) Uani 1 1 d . . .
N1 N 0.88774(12) 0.4643(3) 0.21634(18) 0.0202(5) Uani 1 1 d . . .
C2 C 0.85554(15) 0.2919(5) 0.1446(2) 0.0253(6) Uani 1 1 d . . .
H21 H 0.8029 0.3071 0.1050 0.030 Uiso 1 1 calc R . .
H22 H 0.8674 0.1584 0.1808 0.030 Uiso 1 1 calc R . .
C3 C 0.88274(15) 0.2891(5) 0.0757(2) 0.0255(6) Uani 1 1 d . . .
H31 H 0.8613 0.1712 0.0289 0.031 Uiso 1 1 calc R . .
H32 H 0.8693 0.4195 0.0369 0.031 Uiso 1 1 calc R . .
N4 N 0.96161(13) 0.2676(3) 0.13702(17) 0.0200(5) Uani 1 1 d . . .
H41 H 0.9720 0.1375 0.1669 0.024 Uiso 1 1 calc R . .
C5 C 0.98940(17) 0.2717(5) 0.0719(2) 0.0248(6) Uani 1 1 d . . .
H51 H 0.9772 0.4066 0.0368 0.030 Uiso 1 1 calc R . .
H52 H 0.9659 0.1607 0.0214 0.030 Uiso 1 1 calc R . .
C6 C 1.06957(17) 0.2410(5) 0.1290(2) 0.0272(6) Uani 1 1 d . . .
H61 H 1.0817 0.1173 0.1719 0.033 Uiso 1 1 calc R . .
H62 H 1.0832 0.2104 0.0810 0.033 Uiso 1 1 calc R . .
C7 C 1.11448(17) 0.4211(5) 0.1930(2) 0.0273(6) Uani 1 1 d . . .
H71 H 1.1648 0.3946 0.2149 0.033 Uiso 1 1 calc R . .
H72 H 1.0988 0.5479 0.1516 0.033 Uiso 1 1 calc R . .
C8 C 0.85417(14) 0.6661(4) 0.1748(2) 0.0239(6) Uani 1 1 d . . .
H81 H 0.8502 0.6815 0.1107 0.029 Uiso 1 1 calc R . .
H82 H 0.8877 0.7747 0.2195 0.029 Uiso 1 1 calc R . .
C9 C 0.78155(16) 0.7153(5) 0.1570(3) 0.0318(7) Uani 1 1 d . . .
F91 F 0.73293(12) 0.5644(4) 0.1137(2) 0.0485(8) Uani 0.95 1 d P . .
F92 F 0.78444(12) 0.7641(4) 0.2396(2) 0.0526(7) Uani 0.95 1 d P . .
F93 F 0.75371(11) 0.8819(4) 0.0974(2) 0.0493(6) Uani 0.95 1 d P . .
F91A F 0.745(3) 0.584(8) 0.154(3) 0.026(5) Uiso 0.05 1 d P . .
F92A F 0.7707(19) 0.894(6) 0.175(3) 0.026(5) Uiso 0.05 1 d P . .
F93A F 0.7453(18) 0.763(6) 0.051(3) 0.026(5) Uiso 0.05 1 d P . .


_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 N4 2.100(2) . ?
Ni1 N4 2.100(2) 2_755 ?
Ni1 N1 2.260(2) 2_755 ?
Ni1 N1 2.260(2) . ?
Ni1 Cl1 2.4189(7) 2_755 ?
Ni1 Cl1 2.4189(7) . ?
N1 C8 1.466(3) . ?
N1 C2 1.476(4) . ?
N1 C7 1.509(4) 2_755 ?
C2 C3 1.524(4) . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
C3 N4 1.483(4) . ?
C3 H31 0.9900 . ?
C3 H32 0.9900 . ?
N4 C5 1.478(4) . ?
N4 H41 0.9300 . ?
C5 C6 1.514(4) . ?
C5 H51 0.9900 . ?
C5 H52 0.9900 . ?
C6 C7 1.512(4) . ?
C6 H61 0.9900 . ?
C6 H62 0.9900 . ?
C7 N1 1.509(4) 2_755 ?
C7 H71 0.9900 . ?
C7 H72 0.9900 . ?
C8 C9 1.515(4) . ?
C8 H81 0.9900 . ?
C8 H82 0.9900 . ?
C9 F92A 1.24(4) . ?
C9 F91A 1.16(6) . ?
C9 F91 1.335(4) . ?
C9 F92 1.332(4) . ?
C9 F93 1.345(4) . ?
C9 F93A 1.47(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
N4 Ni1 N4 93.58(13) . 2_755 ?
N4 Ni1 N1 91.95(9) . 2_755 ?
N4 Ni1 N1 82.10(9) 2_755 2_755 ?
N4 Ni1 N1 82.10(9) . . ?
N4 Ni1 N1 91.95(9) 2_755 . ?
N1 Ni1 N1 171.33(11) 2_755 . ?
N4 Ni1 Cl1 171.06(7) . 2_755 ?
N4 Ni1 Cl1 89.67(6) 2_755 2_755 ?
N1 Ni1 Cl1 96.75(6) 2_755 2_755 ?
N1 Ni1 Cl1 89.48(6) . 2_755 ?
N4 Ni1 Cl1 89.67(6) . . ?
N4 Ni1 Cl1 171.06(7) 2_755 . ?
N1 Ni1 Cl1 89.48(6) 2_755 . ?
N1 Ni1 Cl1 96.75(6) . . ?
Cl1 Ni1 Cl1 88.35(3) 2_755 . ?
C8 N1 C2 113.5(2) . . ?
C8 N1 C7 109.1(2) . 2_755 ?
C2 N1 C7 111.0(2) . 2_755 ?
C8 N1 Ni1 105.49(16) . . ?
C2 N1 Ni1 104.46(16) . . ?
C7 N1 Ni1 113.21(17) 2_755 . ?
N1 C2 C3 111.1(2) . . ?
N1 C2 H21 109.4 . . ?
C3 C2 H21 109.4 . . ?
N1 C2 H22 109.4 . . ?
C3 C2 H22 109.4 . . ?
H21 C2 H22 108.0 . . ?
N4 C3 C2 108.2(2) . . ?
N4 C3 H31 110.1 . . ?
C2 C3 H31 110.1 . . ?
N4 C3 H32 110.1 . . ?
C2 C3 H32 110.1 . . ?
H31 C3 H32 108.4 . . ?
C5 N4 C3 109.2(2) . . ?
C5 N4 Ni1 118.01(18) . . ?
C3 N4 Ni1 106.90(17) . . ?
C5 N4 H41 107.4 . . ?
C3 N4 H41 107.4 . . ?
Ni1 N4 H41 107.4 . . ?
N4 C5 C6 112.2(2) . . ?
N4 C5 H51 109.2 . . ?
C6 C5 H51 109.2 . . ?
N4 C5 H52 109.2 . . ?
C6 C5 H52 109.2 . . ?
H51 C5 H52 107.9 . . ?
C7 C6 C5 116.1(2) . . ?
C7 C6 H61 108.3 . . ?
C5 C6 H61 108.3 . . ?
C7 C6 H62 108.3 . . ?
C5 C6 H62 108.3 . . ?
H61 C6 H62 107.4 . . ?
N1 C7 C6 116.2(2) 2_755 . ?
N1 C7 H71 108.2 2_755 . ?
C6 C7 H71 108.2 . . ?
N1 C7 H72 108.2 2_755 . ?
C6 C7 H72 108.2 . . ?
H71 C7 H72 107.4 . . ?
N1 C8 C9 120.0(2) . . ?
N1 C8 H81 107.3 . . ?
C9 C8 H81 107.3 . . ?
N1 C8 H82 107.3 . . ?
C9 C8 H82 107.3 . . ?
H81 C8 H82 106.9 . . ?
F92A C9 F91A 118(3) . . ?
F91 C9 F92 106.1(3) . . ?
F91 C9 F93 106.2(3) . . ?
F92 C9 F93 106.0(3) . . ?
F92A C9 F93A 91(2) . . ?
F91A C9 F93A 100(3) . . ?
F92A C9 C8 118.2(16) . . ?
F91A C9 C8 121(3) . . ?
F91 C9 C8 115.3(3) . . ?
F92 C9 C8 113.0(3) . . ?
F93 C9 C8 109.5(3) . . ?
F93A C9 C8 96.9(14) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.952
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.090
####################################################################### 
# 
# 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_nif2camper
_database_code_depnum_ccdc_archive 'CCDC 1430238'
_audit_update_record             
;
2015-10-08 deposited with the CCDC.
2015-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H26 F6 N4 Ni, 2(Cl O4)'
_chemical_formula_sum            'C14 H26 Cl2 F6 N4 Ni O8'
_chemical_formula_weight         622.00
_chemical_compound_source        'synthesized by the authors'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   8.2589(8)
_cell_length_b                   8.5203(7)
_cell_length_c                   9.2443(8)
_cell_angle_alpha                71.903(4)
_cell_angle_beta                 68.416(3)
_cell_angle_gamma                72.718(3)
_cell_volume                     562.54(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    936
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      24.02

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.836
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             318
_exptl_absorpt_coefficient_mu    1.200
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.890
_exptl_absorpt_correction_T_max  0.931
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1824
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0606
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.57
_diffrn_reflns_theta_max         25.99
_reflns_number_total             1490
_reflns_number_gt                1080
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0675P)²+0.7313P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1490
_refine_ls_number_parameters     160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1331
_refine_ls_wR_factor_gt          0.1168
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni01 Ni 0.5000 0.5000 0.5000 0.0178(4) Uani 1 2 d S . .
N1 N 0.5489(6) 0.6554(6) 0.2846(6) 0.0181(12) Uani 1 1 d . . .
C2 C 0.3770(7) 0.7889(8) 0.2908(8) 0.0267(16) Uani 1 1 d . . .
H21 H 0.3999 0.8898 0.2035 0.032 Uiso 1 1 calc R . .
H22 H 0.2868 0.7437 0.2780 0.032 Uiso 1 1 calc R . .
C3 C 0.3121(8) 0.8341(8) 0.4468(8) 0.0283(17) Uani 1 1 d . . .
H31 H 0.1926 0.9088 0.4605 0.034 Uiso 1 1 calc R . .
H32 H 0.3936 0.8955 0.4522 0.034 Uiso 1 1 calc R . .
N4 N 0.3030(6) 0.6777(6) 0.5758(6) 0.0207(13) Uani 1 1 d . . .
H41 H 0.2078 0.6482 0.5756 0.025 Uiso 1 1 d R . .
C5 C 0.2755(8) 0.7148(8) 0.7288(8) 0.0304(17) Uani 1 1 d . . .
H51 H 0.1683 0.8056 0.7496 0.036 Uiso 1 1 calc R . .
H52 H 0.3785 0.7578 0.7200 0.036 Uiso 1 1 calc R . .
C6 C 0.2532(8) 0.5661(8) 0.8687(8) 0.0291(16) Uani 1 1 d . . .
H61 H 0.2305 0.6029 0.9672 0.035 Uiso 1 1 calc R . .
H62 H 0.1481 0.5247 0.8801 0.035 Uiso 1 1 calc R . .
C7 C 0.4129(8) 0.4248(8) 0.8515(8) 0.0271(16) Uani 1 1 d . . .
H71 H 0.3956 0.3368 0.9521 0.033 Uiso 1 1 calc R . .
H72 H 0.5181 0.4681 0.8363 0.033 Uiso 1 1 calc R . .
C8 C 0.6976(8) 0.7286(8) 0.2719(7) 0.0237(15) Uani 1 1 d . . .
H81 H 0.7991 0.6336 0.2842 0.028 Uiso 1 1 calc R . .
H82 H 0.6595 0.7798 0.3649 0.028 Uiso 1 1 calc R . .
C9 C 0.7685(8) 0.8604(8) 0.1229(8) 0.0252(16) Uani 1 1 d . . .
F91 F 0.8361(5) 0.8038(5) -0.0108(5) 0.0449(11) Uani 1 1 d . . .
F92 F 0.9019(5) 0.9018(5) 0.1417(5) 0.0484(12) Uani 1 1 d . . .
F93 F 0.6494(5) 1.0019(5) 0.0981(5) 0.0491(13) Uani 1 1 d . . .
Cl1 Cl 0.17851(18) 0.32501(19) 0.35892(18) 0.0232(4) Uani 1 1 d . . .
O11 O 0.2387(6) 0.4372(6) 0.4068(6) 0.0355(12) Uani 1 1 d . . .
O12 O 0.3306(5) 0.2197(6) 0.2702(6) 0.0359(13) Uani 1 1 d . . .
O13 O 0.0780(6) 0.2219(5) 0.4987(6) 0.0391(13) Uani 1 1 d . . .
O14 O 0.0671(6) 0.4239(6) 0.2595(6) 0.0402(13) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni01 N4 1.946(5) 2_666 ?
Ni01 N4 1.946(5) . ?
Ni01 N1 1.992(5) 2_666 ?
Ni01 N1 1.992(5) . ?
N1 C8 1.488(7) . ?
N1 C7 1.504(8) 2_666 ?
N1 C2 1.528(8) . ?
C2 C3 1.472(9) . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
C3 N4 1.487(7) . ?
C3 H31 0.9900 . ?
C3 H32 0.9900 . ?
N4 C5 1.466(8) . ?
N4 H41 0.8947 . ?
C5 C6 1.502(8) . ?
C5 H51 0.9900 . ?
C5 H52 0.9900 . ?
C6 C7 1.495(9) . ?
C6 H61 0.9900 . ?
C6 H62 0.9900 . ?
C7 N1 1.504(8) 2_666 ?
C7 H71 0.9900 . ?
C7 H72 0.9900 . ?
C8 C9 1.529(8) . ?
C8 H81 0.9900 . ?
C8 H82 0.9900 . ?
C9 F93 1.328(7) . ?
C9 F91 1.333(8) . ?
C9 F92 1.333(7) . ?
Cl1 O11 1.436(5) . ?
Cl1 O13 1.438(4) . ?
Cl1 O14 1.443(5) . ?
Cl1 O12 1.444(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 Ni01 N4 180.000(1) 2_666 . ?
N4 Ni01 N1 87.92(19) 2_666 2_666 ?
N4 Ni01 N1 92.08(19) . 2_666 ?
N4 Ni01 N1 92.08(19) 2_666 . ?
N4 Ni01 N1 87.92(19) . . ?
N1 Ni01 N1 180.000(1) 2_666 . ?
C8 N1 C7 113.2(4) . 2_666 ?
C8 N1 C2 111.5(4) . . ?
C7 N1 C2 107.6(5) 2_666 . ?
C8 N1 Ni01 104.9(3) . . ?
C7 N1 Ni01 114.8(3) 2_666 . ?
C2 N1 Ni01 104.6(3) . . ?
C3 C2 N1 107.9(5) . . ?
C3 C2 H21 110.1 . . ?
N1 C2 H21 110.1 . . ?
C3 C2 H22 110.1 . . ?
N1 C2 H22 110.1 . . ?
H21 C2 H22 108.4 . . ?
C2 C3 N4 109.2(5) . . ?
C2 C3 H31 109.8 . . ?
N4 C3 H31 109.8 . . ?
C2 C3 H32 109.8 . . ?
N4 C3 H32 109.8 . . ?
H31 C3 H32 108.3 . . ?
C5 N4 C3 110.4(5) . . ?
C5 N4 Ni01 119.7(4) . . ?
C3 N4 Ni01 108.4(4) . . ?
C5 N4 H41 111.5 . . ?
C3 N4 H41 101.8 . . ?
Ni01 N4 H41 103.6 . . ?
N4 C5 C6 114.3(5) . . ?
N4 C5 H51 108.7 . . ?
C6 C5 H51 108.7 . . ?
N4 C5 H52 108.7 . . ?
C6 C5 H52 108.7 . . ?
H51 C5 H52 107.6 . . ?
C7 C6 C5 112.6(5) . . ?
C7 C6 H61 109.1 . . ?
C5 C6 H61 109.1 . . ?
C7 C6 H62 109.1 . . ?
C5 C6 H62 109.1 . . ?
H61 C6 H62 107.8 . . ?
C6 C7 N1 114.5(5) . 2_666 ?
C6 C7 H71 108.6 . . ?
N1 C7 H71 108.6 2_666 . ?
C6 C7 H72 108.6 . . ?
N1 C7 H72 108.6 2_666 . ?
H71 C7 H72 107.6 . . ?
N1 C8 C9 120.2(5) . . ?
N1 C8 H81 107.3 . . ?
C9 C8 H81 107.3 . . ?
N1 C8 H82 107.3 . . ?
C9 C8 H82 107.3 . . ?
H81 C8 H82 106.9 . . ?
F93 C9 F91 107.6(6) . . ?
F93 C9 F92 107.1(5) . . ?
F91 C9 F92 106.2(5) . . ?
F93 C9 C8 114.1(5) . . ?
F91 C9 C8 113.6(5) . . ?
F92 C9 C8 107.7(5) . . ?
O11 Cl1 O13 109.3(3) . . ?
O11 Cl1 O14 108.9(3) . . ?
O13 Cl1 O14 109.7(3) . . ?
O11 Cl1 O12 109.3(3) . . ?
O13 Cl1 O12 110.0(3) . . ?
O14 Cl1 O12 109.8(3) . . ?

_diffrn_measured_fraction_theta_max 0.674
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.674
_refine_diff_density_max         0.882
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.098
####################################################################### 
# 
# 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_nif2te2p
_database_code_depnum_ccdc_archive 'CCDC 1430239'
_audit_update_record             
;
2015-10-08 deposited with the CCDC.
2015-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H29 F6 N4 Ni O6 P2, H4 N, 3.25(H2 O)'
_chemical_formula_sum            'C16 H39.50 F6 N5 Ni O9.25 P2'
_chemical_formula_weight         684.68
_chemical_compound_source        'synthesized by the authors'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   9.4281(4)
_cell_length_b                   16.7420(7)
_cell_length_c                   17.0428(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.3100(10)
_cell_angle_gamma                90.00
_cell_volume                     2690.09(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7487
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      27.49

_exptl_crystal_description       bar
_exptl_crystal_colour            'light blue'
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.691
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1426
_exptl_absorpt_coefficient_mu    0.938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5860
_exptl_absorpt_correction_T_max  0.9112
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22327
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         27.50
_reflns_number_total             6159
_reflns_number_gt                4968
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0355P)²+1.8597P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6159
_refine_ls_number_parameters     375
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0803
_refine_ls_wR_factor_gt          0.0735
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.47191(2) 0.763060(15) 0.206858(13) 0.00898(7) Uani 1 1 d . . .
N1 N 0.24963(17) 0.75757(10) 0.21847(9) 0.0126(3) Uani 1 1 d . . .
C2 C 0.2037(2) 0.71100(13) 0.14858(11) 0.0167(4) Uani 1 1 d . . .
H21 H 0.2096 0.7451 0.1012 0.020 Uiso 1 1 calc R . .
H22 H 0.1037 0.6943 0.1550 0.020 Uiso 1 1 calc R . .
C3 C 0.2963(2) 0.63775(13) 0.13789(12) 0.0173(4) Uani 1 1 d . . .
H31 H 0.2933 0.6044 0.1858 0.021 Uiso 1 1 calc R . .
H32 H 0.2603 0.6055 0.0934 0.021 Uiso 1 1 calc R . .
N4 N 0.44523(17) 0.66309(10) 0.12236(9) 0.0131(3) Uani 1 1 d . . .
C5 C 0.5472(2) 0.59839(12) 0.14512(12) 0.0166(4) Uani 1 1 d . . .
H51 H 0.5323 0.5521 0.1099 0.020 Uiso 1 1 calc R . .
H52 H 0.5254 0.5808 0.1992 0.020 Uiso 1 1 calc R . .
C6 C 0.7032(2) 0.62282(12) 0.14168(12) 0.0181(4) Uani 1 1 d . . .
H61 H 0.7617 0.5739 0.1464 0.022 Uiso 1 1 calc R . .
H62 H 0.7215 0.6459 0.0892 0.022 Uiso 1 1 calc R . .
C7 C 0.7541(2) 0.68244(12) 0.20345(12) 0.0160(4) Uani 1 1 d . . .
H71 H 0.7310 0.6609 0.2560 0.019 Uiso 1 1 calc R . .
H72 H 0.8586 0.6865 0.2002 0.019 Uiso 1 1 calc R . .
N8 N 0.69304(16) 0.76452(10) 0.19693(9) 0.0112(3) Uani 1 1 d . . .
C9 C 0.7375(2) 0.81248(13) 0.26628(11) 0.0145(4) Uani 1 1 d . . .
H91 H 0.8378 0.8287 0.2602 0.017 Uiso 1 1 calc R . .
H92 H 0.7307 0.7791 0.3141 0.017 Uiso 1 1 calc R . .
C10 C 0.6460(2) 0.88654(12) 0.27603(11) 0.0147(4) Uani 1 1 d . . .
H101 H 0.6832 0.9194 0.3199 0.018 Uiso 1 1 calc R . .
H102 H 0.6494 0.9191 0.2276 0.018 Uiso 1 1 calc R . .
N11 N 0.49608(17) 0.86286(10) 0.29247(9) 0.0119(3) Uani 1 1 d . . .
C12 C 0.3920(2) 0.92586(12) 0.26932(12) 0.0150(4) Uani 1 1 d . . .
H121 H 0.4111 0.9423 0.2146 0.018 Uiso 1 1 calc R . .
H122 H 0.4063 0.9732 0.3033 0.018 Uiso 1 1 calc R . .
C13 C 0.2373(2) 0.89897(12) 0.27536(12) 0.0162(4) Uani 1 1 d . . .
H131 H 0.2234 0.8756 0.3281 0.019 Uiso 1 1 calc R . .
H132 H 0.1765 0.9470 0.2718 0.019 Uiso 1 1 calc R . .
C14 C 0.1843(2) 0.83860(12) 0.21468(11) 0.0153(4) Uani 1 1 d . . .
H141 H 0.0805 0.8328 0.2209 0.018 Uiso 1 1 calc R . .
H142 H 0.2013 0.8609 0.1618 0.018 Uiso 1 1 calc R . .
C15 C 0.2045(2) 0.71477(12) 0.29174(11) 0.0142(4) Uani 1 1 d . . .
H151 H 0.1219 0.6805 0.2793 0.017 Uiso 1 1 calc R . .
H152 H 0.1740 0.7547 0.3310 0.017 Uiso 1 1 calc R . .
P1 P 0.34546(5) 0.65268(3) 0.33482(3) 0.01194(11) Uani 1 1 d . . .
O11 O 0.48181(14) 0.68401(8) 0.29960(7) 0.0136(3) Uani 1 1 d . . .
O12 O 0.34487(15) 0.67430(9) 0.42454(8) 0.0169(3) Uani 1 1 d . . .
H12O H 0.2610 0.6625 0.4513 0.020 Uiso 1 1 d R . .
O13 O 0.31659(15) 0.56524(8) 0.32360(8) 0.0180(3) Uani 1 1 d . . .
C16 C 0.7447(2) 0.80457(12) 0.12352(11) 0.0126(4) Uani 1 1 d . . .
H161 H 0.7709 0.7630 0.0849 0.015 Uiso 1 1 calc R . .
H162 H 0.8313 0.8355 0.1362 0.015 Uiso 1 1 calc R . .
P2 P 0.61365(5) 0.87165(3) 0.07862(3) 0.01213(11) Uani 1 1 d . . .
O21 O 0.47216(14) 0.84715(8) 0.11531(7) 0.0126(3) Uani 1 1 d . . .
O22 O 0.61747(15) 0.85272(9) -0.00972(8) 0.0184(3) Uani 1 1 d . . .
O23 O 0.65375(16) 0.95795(9) 0.09349(8) 0.0195(3) Uani 1 1 d . . .
C17 C 0.4615(2) 0.69075(13) 0.04036(11) 0.0168(4) Uani 1 1 d . . .
H171 H 0.5539 0.7187 0.0369 0.020 Uiso 1 1 calc R . .
H172 H 0.3869 0.7312 0.0304 0.020 Uiso 1 1 calc R . .
C18 C 0.4554(2) 0.63087(14) -0.02621(12) 0.0220(5) Uani 1 1 d . . .
F181 F 0.33902(15) 0.58613(10) -0.02961(8) 0.0445(4) Uani 1 1 d . . .
F182 F 0.56459(15) 0.57980(9) -0.02732(8) 0.0336(3) Uani 1 1 d . . .
F183 F 0.46264(17) 0.67118(9) -0.09440(7) 0.0387(4) Uani 1 1 d . . .
C19 C 0.4824(2) 0.83930(12) 0.37567(11) 0.0140(4) Uani 1 1 d . . .
H191 H 0.5638 0.8044 0.3890 0.017 Uiso 1 1 calc R . .
H192 H 0.3955 0.8065 0.3806 0.017 Uiso 1 1 calc R . .
C20 C 0.4755(2) 0.90504(13) 0.43689(12) 0.0181(4) Uani 1 1 d . . .
F201 F 0.56842(14) 0.96470(8) 0.42709(7) 0.0269(3) Uani 1 1 d . . .
F202 F 0.34734(13) 0.93961(8) 0.44171(7) 0.0270(3) Uani 1 1 d . . .
F203 F 0.50162(16) 0.87321(9) 0.50789(7) 0.0323(3) Uani 1 1 d . . .
N1A N 0.72697(18) 0.03158(10) 0.94777(9) 0.0160(4) Uani 1 1 d . . .
H11A H 0.7520 -0.0023 0.9081 0.019 Uiso 1 1 d R . .
H12A H 0.7003 0.0010 0.9901 0.019 Uiso 1 1 d R . .
H13A H 0.8051 0.0620 0.9643 0.019 Uiso 1 1 d R . .
H14A H 0.6598 0.0668 0.9301 0.019 Uiso 1 1 d R . .
O1W O 0.8945(2) 0.62145(12) 0.38309(11) 0.0567(7) Uani 1 1 d . . .
H11W H 0.8976 0.5725 0.3788 0.068 Uiso 1 1 d R . .
H12W H 0.9588 0.6309 0.4147 0.068 Uiso 1 1 d R . .
O2WA O -0.0741(2) 0.96959(13) 0.17639(16) 0.0496(10) Uani 0.879(7) 1 d P A 1
H21W H 0.0035 1.0056 0.1684 0.060 Uiso 1 1 d R . .
H22W H -0.1440 0.9936 0.1566 0.060 Uiso 0.879(7) 1 d PR A 1
O2WB O -0.0379(18) 0.9623(10) 0.1160(13) 0.0496(10) Uani 0.12 1 d P A 2
H23W H -0.1244 0.9796 0.1157 0.060 Uiso 0.121(7) 1 d PR A 2
O3WA O 0.8527(5) 0.1701(2) 0.0190(3) 0.0405(16) Uani 0.686(12) 1 d P B 3
H31W H 0.8127 0.1669 0.0672 0.049 Uiso 0.686(12) 1 d PR B 3
H32W H 0.9359 0.1732 0.0377 0.049 Uiso 0.686(12) 1 d PR B 3
O3WB O 0.7911(12) 0.1958(7) 0.0544(6) 0.055(3) Uani 0.314(12) 1 d P B 4
H33W H 0.7251 0.1699 0.0768 0.066 Uiso 0.314(12) 1 d PR B 4
H34W H 0.8497 0.1926 0.0924 0.066 Uiso 0.314(12) 1 d PR B 4
O4W O -0.0037(7) 0.9313(6) 0.0204(4) 0.054(3) Uani 0.25 1 d P C 5
H41W H -0.0492 0.8982 -0.0080 0.065 Uiso 0.25 1 d PR C 5
H42W H -0.0011 0.9800 0.0066 0.065 Uiso 0.25 1 d PR C 5


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O11 2.0632(13) . ?
Ni1 N8 2.0928(16) . ?
Ni1 O21 2.1015(13) . ?
Ni1 N1 2.1081(16) . ?
Ni1 N4 2.2213(16) . ?
Ni1 N11 2.2292(16) . ?
N1 C2 1.486(2) . ?
N1 C14 1.491(3) . ?
N1 C15 1.503(2) . ?
C2 C3 1.517(3) . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
C3 N4 1.492(3) . ?
C3 H31 0.9900 . ?
C3 H32 0.9900 . ?
N4 C17 1.481(2) . ?
N4 C5 1.498(3) . ?
C5 C6 1.528(3) . ?
C5 H51 0.9900 . ?
C5 H52 0.9900 . ?
C6 C7 1.526(3) . ?
C6 H61 0.9900 . ?
C6 H62 0.9900 . ?
C7 N8 1.494(3) . ?
C7 H71 0.9900 . ?
C7 H72 0.9900 . ?
N8 C9 1.487(2) . ?
N8 C16 1.503(2) . ?
C9 C10 1.520(3) . ?
C9 H91 0.9900 . ?
C9 H92 0.9900 . ?
C10 N11 1.496(2) . ?
C10 H101 0.9900 . ?
C10 H102 0.9900 . ?
N11 C19 1.478(2) . ?
N11 C12 1.492(2) . ?
C12 C13 1.530(3) . ?
C12 H121 0.9900 . ?
C12 H122 0.9900 . ?
C13 C14 1.528(3) . ?
C13 H131 0.9900 . ?
C13 H132 0.9900 . ?
C14 H141 0.9900 . ?
C14 H142 0.9900 . ?
C15 P1 1.837(2) . ?
C15 H151 0.9900 . ?
C15 H152 0.9900 . ?
P1 O13 1.5010(15) . ?
P1 O11 1.5153(14) . ?
P1 O12 1.5714(14) . ?
O12 H12O 0.9360 . ?
C16 P2 1.8340(19) . ?
C16 H161 0.9900 . ?
C16 H162 0.9900 . ?
P2 O23 1.5146(15) . ?
P2 O21 1.5322(14) . ?
P2 O22 1.5392(14) . ?
C17 C18 1.515(3) . ?
C17 H171 0.9900 . ?
C17 H172 0.9900 . ?
C18 F181 1.329(3) . ?
C18 F182 1.339(3) . ?
C18 F183 1.346(3) . ?
C19 C20 1.518(3) . ?
C19 H191 0.9900 . ?
C19 H192 0.9900 . ?
C20 F201 1.339(2) . ?
C20 F202 1.343(2) . ?
C20 F203 1.344(2) . ?
N1A H11A 0.9144 . ?
N1A H12A 0.9211 . ?
N1A H13A 0.9372 . ?
N1A H14A 0.9154 . ?
O1W H11W 0.8239 . ?
O1W H12W 0.8239 . ?
O2WA H21W 0.9574 . ?
O2WA H22W 0.8412 . ?
O2WB H21W 1.2126 . ?
O2WB H23W 0.8657 . ?
O3WA H31W 0.9078 . ?
O3WA H32W 0.8472 . ?
O3WB H33W 0.8500 . ?
O3WB H34W 0.8507 . ?
O4W H41W 0.8498 . ?
O4W H42W 0.8496 . ?

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
O11 Ni1 N8 91.63(6) . . ?
O11 Ni1 O21 176.61(5) . . ?
N8 Ni1 O21 85.82(6) . . ?
O11 Ni1 N1 86.62(6) . . ?
N8 Ni1 N1 178.02(6) . . ?
O21 Ni1 N1 95.97(6) . . ?
O11 Ni1 N4 91.02(6) . . ?
N8 Ni1 N4 93.77(6) . . ?
O21 Ni1 N4 91.37(6) . . ?
N1 Ni1 N4 85.35(6) . . ?
O11 Ni1 N11 88.59(6) . . ?
N8 Ni1 N11 86.89(6) . . ?
O21 Ni1 N11 89.04(6) . . ?
N1 Ni1 N11 93.98(6) . . ?
N4 Ni1 N11 179.24(6) . . ?
C2 N1 C14 108.92(15) . . ?
C2 N1 C15 109.47(15) . . ?
C14 N1 C15 110.56(15) . . ?
C2 N1 Ni1 103.47(12) . . ?
C14 N1 Ni1 111.51(12) . . ?
C15 N1 Ni1 112.62(11) . . ?
N1 C2 C3 110.80(16) . . ?
N1 C2 H21 109.5 . . ?
C3 C2 H21 109.5 . . ?
N1 C2 H22 109.5 . . ?
C3 C2 H22 109.5 . . ?
H21 C2 H22 108.1 . . ?
N4 C3 C2 109.52(17) . . ?
N4 C3 H31 109.8 . . ?
C2 C3 H31 109.8 . . ?
N4 C3 H32 109.8 . . ?
C2 C3 H32 109.8 . . ?
H31 C3 H32 108.2 . . ?
C17 N4 C3 111.03(15) . . ?
C17 N4 C5 113.62(15) . . ?
C3 N4 C5 110.60(16) . . ?
C17 N4 Ni1 111.36(12) . . ?
C3 N4 Ni1 101.69(11) . . ?
C5 N4 Ni1 107.86(11) . . ?
N4 C5 C6 114.40(17) . . ?
N4 C5 H51 108.7 . . ?
C6 C5 H51 108.7 . . ?
N4 C5 H52 108.7 . . ?
C6 C5 H52 108.7 . . ?
H51 C5 H52 107.6 . . ?
C7 C6 C5 116.58(17) . . ?
C7 C6 H61 108.1 . . ?
C5 C6 H61 108.1 . . ?
C7 C6 H62 108.1 . . ?
C5 C6 H62 108.1 . . ?
H61 C6 H62 107.3 . . ?
N8 C7 C6 115.54(16) . . ?
N8 C7 H71 108.4 . . ?
C6 C7 H71 108.4 . . ?
N8 C7 H72 108.4 . . ?
C6 C7 H72 108.4 . . ?
H71 C7 H72 107.5 . . ?
C9 N8 C7 109.32(14) . . ?
C9 N8 C16 109.24(15) . . ?
C7 N8 C16 110.24(15) . . ?
C9 N8 Ni1 102.64(11) . . ?
C7 N8 Ni1 111.51(12) . . ?
C16 N8 Ni1 113.57(11) . . ?
N8 C9 C10 111.69(15) . . ?
N8 C9 H91 109.3 . . ?
C10 C9 H91 109.3 . . ?
N8 C9 H92 109.3 . . ?
C10 C9 H92 109.3 . . ?
H91 C9 H92 107.9 . . ?
N11 C10 C9 109.98(16) . . ?
N11 C10 H101 109.7 . . ?
C9 C10 H101 109.7 . . ?
N11 C10 H102 109.7 . . ?
C9 C10 H102 109.7 . . ?
H101 C10 H102 108.2 . . ?
C19 N11 C12 112.43(15) . . ?
C19 N11 C10 109.75(15) . . ?
C12 N11 C10 112.58(15) . . ?
C19 N11 Ni1 114.75(12) . . ?
C12 N11 Ni1 106.97(11) . . ?
C10 N11 Ni1 99.75(11) . . ?
N11 C12 C13 113.56(16) . . ?
N11 C12 H121 108.9 . . ?
C13 C12 H121 108.9 . . ?
N11 C12 H122 108.9 . . ?
C13 C12 H122 108.9 . . ?
H121 C12 H122 107.7 . . ?
C14 C13 C12 117.22(17) . . ?
C14 C13 H131 108.0 . . ?
C12 C13 H131 108.0 . . ?
C14 C13 H132 108.0 . . ?
C12 C13 H132 108.0 . . ?
H131 C13 H132 107.2 . . ?
N1 C14 C13 116.04(15) . . ?
N1 C14 H141 108.3 . . ?
C13 C14 H141 108.3 . . ?
N1 C14 H142 108.3 . . ?
C13 C14 H142 108.3 . . ?
H141 C14 H142 107.4 . . ?
N1 C15 P1 113.24(13) . . ?
N1 C15 H151 108.9 . . ?
P1 C15 H151 108.9 . . ?
N1 C15 H152 108.9 . . ?
P1 C15 H152 108.9 . . ?
H151 C15 H152 107.7 . . ?
O13 P1 O11 116.15(8) . . ?
O13 P1 O12 110.30(8) . . ?
O11 P1 O12 108.25(8) . . ?
O13 P1 C15 111.76(9) . . ?
O11 P1 C15 105.02(8) . . ?
O12 P1 C15 104.61(9) . . ?
P1 O11 Ni1 119.37(8) . . ?
P1 O12 H12O 115.6 . . ?
N8 C16 P2 113.58(13) . . ?
N8 C16 H161 108.9 . . ?
P2 C16 H161 108.9 . . ?
N8 C16 H162 108.9 . . ?
P2 C16 H162 108.9 . . ?
H161 C16 H162 107.7 . . ?
O23 P2 O21 113.84(8) . . ?
O23 P2 O22 110.67(8) . . ?
O21 P2 O22 111.66(8) . . ?
O23 P2 C16 110.33(9) . . ?
O21 P2 C16 104.58(8) . . ?
O22 P2 C16 105.24(9) . . ?
P2 O21 Ni1 119.13(7) . . ?
N4 C17 C18 119.73(18) . . ?
N4 C17 H171 107.4 . . ?
C18 C17 H171 107.4 . . ?
N4 C17 H172 107.4 . . ?
C18 C17 H172 107.4 . . ?
H171 C17 H172 106.9 . . ?
F181 C18 F182 105.91(19) . . ?
F181 C18 F183 106.91(18) . . ?
F182 C18 F183 105.37(17) . . ?
F181 C18 C17 115.73(18) . . ?
F182 C18 C17 114.00(17) . . ?
F183 C18 C17 108.23(19) . . ?
N11 C19 C20 118.04(17) . . ?
N11 C19 H191 107.8 . . ?
C20 C19 H191 107.8 . . ?
N11 C19 H192 107.8 . . ?
C20 C19 H192 107.8 . . ?
H191 C19 H192 107.1 . . ?
F201 C20 F202 106.00(17) . . ?
F201 C20 F203 106.93(16) . . ?
F202 C20 F203 106.05(16) . . ?
F201 C20 C19 115.12(17) . . ?
F202 C20 C19 113.35(17) . . ?
F203 C20 C19 108.84(17) . . ?
H11A N1A H12A 107.9 . . ?
H11A N1A H13A 110.7 . . ?
H12A N1A H13A 106.5 . . ?
H11A N1A H14A 109.7 . . ?
H12A N1A H14A 115.1 . . ?
H13A N1A H14A 106.9 . . ?
H11W O1W H12W 102.9 . . ?
H21W O2WA H22W 103.9 . . ?
H21W O2WB H23W 95.9 . . ?
H31W O3WA H32W 92.9 . . ?
H33W O3WB H34W 95.8 . . ?
H41W O4W H42W 118.8 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.663
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.076
####################################################################### 
# 
# 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_nitfe2cam
_database_code_depnum_ccdc_archive 'CCDC 1430240'
_audit_update_record             
;
2015-10-08 deposited with the CCDC.
2015-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H30 F6 N4 Ni O2, 2(C7 H7 O3 S)'
_chemical_formula_sum            'C28 H44 F6 N4 Ni O8 S2'
_chemical_formula_weight         801.50
_chemical_compound_source        'synthesized by the authors'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   8.7262(3)
_cell_length_b                   25.5904(15)
_cell_length_c                   30.9247(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     6905.7(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3326
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      25.05

_exptl_crystal_description       bar
_exptl_crystal_colour            'light blue'
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3344
_exptl_absorpt_coefficient_mu    0.768
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22423
_diffrn_reflns_av_R_equivalents  0.0722
_diffrn_reflns_av_sigmaI/netI    0.0916
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.59
_diffrn_reflns_theta_max         26.00
_reflns_number_total             6742
_reflns_number_gt                4408
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0489P)²+2.3487P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6742
_refine_ls_number_parameters     444
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1029
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.1212
_refine_ls_wR_factor_gt          0.1060
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.09739(5) 0.121526(19) 0.102302(15) 0.01167(14) Uani 1 1 d . . .
O1W O -0.1354(3) 0.12934(10) 0.08642(8) 0.0172(6) Uani 1 1 d . . .
H21W H -0.2113 0.1423 0.1046 0.021 Uiso 1 1 d R . .
H22W H -0.1678 0.1007 0.0732 0.021 Uiso 1 1 d R . .
O2W O 0.0832(3) 0.05358(10) 0.06606(8) 0.0161(6) Uani 1 1 d . . .
H11W H 0.1153 0.0474 0.0413 0.019 Uiso 1 1 d R . .
H12W H 0.0154 0.0238 0.0669 0.019 Uiso 1 1 d R . .
N1 N 0.0670(3) 0.07557(12) 0.16246(10) 0.0147(7) Uani 1 1 d . . .
C2 C 0.0918(4) 0.11463(15) 0.19783(12) 0.0195(9) Uani 1 1 d . . .
H21 H 0.2030 0.1192 0.2029 0.023 Uiso 1 1 calc R . .
H22 H 0.0447 0.1017 0.2249 0.023 Uiso 1 1 calc R . .
C3 C 0.0213(4) 0.16637(16) 0.18556(13) 0.0194(10) Uani 1 1 d . . .
H31 H -0.0908 0.1623 0.1819 0.023 Uiso 1 1 calc R . .
H32 H 0.0398 0.1923 0.2088 0.023 Uiso 1 1 calc R . .
N4 N 0.0902(3) 0.18494(12) 0.14466(10) 0.0142(7) Uani 1 1 d . . .
H41 H 0.1915 0.1933 0.1510 0.017 Uiso 1 1 calc R . .
C5 C 0.0161(4) 0.23424(16) 0.13033(14) 0.0231(10) Uani 1 1 d . . .
H51 H 0.0191 0.2599 0.1543 0.028 Uiso 1 1 calc R . .
H52 H -0.0927 0.2273 0.1233 0.028 Uiso 1 1 calc R . .
C6 C 0.0941(5) 0.25704(16) 0.09139(14) 0.0266(10) Uani 1 1 d . . .
H61 H 0.2050 0.2598 0.0977 0.032 Uiso 1 1 calc R . .
H62 H 0.0549 0.2930 0.0871 0.032 Uiso 1 1 calc R . .
C7 C 0.0754(5) 0.22734(16) 0.04921(14) 0.0267(10) Uani 1 1 d . . .
H71 H -0.0355 0.2223 0.0439 0.032 Uiso 1 1 calc R . .
H72 H 0.1154 0.2495 0.0255 0.032 Uiso 1 1 calc R . .
N8 N 0.1521(3) 0.17525(12) 0.04662(11) 0.0164(8) Uani 1 1 d . . .
C9 C 0.3228(4) 0.17992(16) 0.04905(14) 0.0203(10) Uani 1 1 d . . .
H91 H 0.3507 0.2067 0.0707 0.024 Uiso 1 1 calc R . .
H92 H 0.3633 0.1912 0.0206 0.024 Uiso 1 1 calc R . .
C10 C 0.3936(4) 0.12840(16) 0.06139(13) 0.0202(10) Uani 1 1 d . . .
H101 H 0.3686 0.1017 0.0394 0.024 Uiso 1 1 calc R . .
H102 H 0.5065 0.1319 0.0629 0.024 Uiso 1 1 calc R . .
N11 N 0.3332(3) 0.11227(12) 0.10382(10) 0.0147(7) Uani 1 1 d . . .
H111 H 0.3705 0.1361 0.1239 0.018 Uiso 1 1 calc R . .
C12 C 0.3939(4) 0.06043(15) 0.11635(13) 0.0193(9) Uani 1 1 d . . .
H121 H 0.5072 0.0612 0.1149 0.023 Uiso 1 1 calc R . .
H122 H 0.3574 0.0340 0.0954 0.023 Uiso 1 1 calc R . .
C13 C 0.3454(4) 0.04446(16) 0.16123(13) 0.0218(10) Uani 1 1 d . . .
H131 H 0.3704 0.0734 0.1813 0.026 Uiso 1 1 calc R . .
H132 H 0.4075 0.0139 0.1700 0.026 Uiso 1 1 calc R . .
C14 C 0.1767(4) 0.03062(15) 0.16695(14) 0.0184(9) Uani 1 1 d . . .
H141 H 0.1492 0.0037 0.1453 0.022 Uiso 1 1 calc R . .
H142 H 0.1629 0.0149 0.1960 0.022 Uiso 1 1 calc R . .
C15 C -0.0936(4) 0.05546(15) 0.16319(13) 0.0169(9) Uani 1 1 d . . .
H151 H -0.1132 0.0386 0.1349 0.020 Uiso 1 1 calc R . .
H152 H -0.1626 0.0861 0.1650 0.020 Uiso 1 1 calc R . .
C16 C -0.1418(4) 0.01762(18) 0.19780(14) 0.0242(10) Uani 1 1 d . . .
F161 F -0.2953(2) 0.01299(10) 0.19715(8) 0.0363(7) Uani 1 1 d . . .
F162 F -0.0879(3) -0.03120(9) 0.19126(9) 0.0375(7) Uani 1 1 d . . .
F163 F -0.1018(3) 0.03036(12) 0.23803(8) 0.0474(8) Uani 1 1 d . . .
C17 C 0.1046(4) 0.14835(15) 0.00629(13) 0.0193(9) Uani 1 1 d . . .
H171 H -0.0019 0.1360 0.0104 0.023 Uiso 1 1 calc R . .
H172 H 0.1697 0.1169 0.0031 0.023 Uiso 1 1 calc R . .
C18 C 0.1105(5) 0.17809(18) -0.03597(15) 0.0316(11) Uani 1 1 d . . .
F181 F 0.1052(3) 0.14421(10) -0.06886(8) 0.0432(7) Uani 1 1 d . . .
F182 F -0.0119(3) 0.20948(11) -0.04194(9) 0.0549(8) Uani 1 1 d . . .
F183 F 0.2338(3) 0.20768(12) -0.04187(9) 0.0573(9) Uani 1 1 d . . .
S1T S 0.58032(10) 0.18681(4) 0.17330(3) 0.0171(2) Uani 1 1 d . . .
O1T O 0.6399(3) 0.18219(11) 0.12945(9) 0.0233(7) Uani 1 1 d . . .
O3T O 0.4151(3) 0.19446(12) 0.17286(10) 0.0313(8) Uani 1 1 d . . .
O2T O 0.6307(3) 0.14464(11) 0.20133(10) 0.0288(7) Uani 1 1 d . . .
C1T C 0.6583(4) 0.24565(15) 0.19439(13) 0.0131(9) Uani 1 1 d . . .
C2T C 0.6359(4) 0.29218(16) 0.17229(14) 0.0198(9) Uani 1 1 d . . .
H21T H 0.5807 0.2924 0.1458 0.024 Uiso 1 1 calc R . .
C3T C 0.6936(4) 0.33788(16) 0.18872(14) 0.0228(10) Uani 1 1 d . . .
H31T H 0.6781 0.3696 0.1734 0.027 Uiso 1 1 calc R . .
C4T C 0.7746(4) 0.33840(16) 0.22747(14) 0.0202(9) Uani 1 1 d . . .
C5T C 0.7987(4) 0.29226(16) 0.24884(14) 0.0202(9) Uani 1 1 d . . .
H51T H 0.8559 0.2922 0.2750 0.024 Uiso 1 1 calc R . .
C6T C 0.7404(4) 0.24542(15) 0.23268(12) 0.0145(9) Uani 1 1 d . . .
H61T H 0.7570 0.2136 0.2478 0.017 Uiso 1 1 calc R . .
C7T C 0.8355(5) 0.38958(17) 0.24595(16) 0.0336(11) Uani 1 1 d . . .
H71T H 0.7569 0.4057 0.2642 0.050 Uiso 1 1 calc R . .
H72T H 0.8617 0.4133 0.2222 0.050 Uiso 1 1 calc R . .
H73T H 0.9272 0.3826 0.2633 0.050 Uiso 1 1 calc R . .
S1U S 0.75521(10) 0.48713(4) 0.04966(3) 0.0157(2) Uani 1 1 d . . .
O1U O 0.7936(3) 0.54232(10) 0.05330(9) 0.0183(6) Uani 1 1 d . . .
O2U O 0.7481(3) 0.47044(10) 0.00503(9) 0.0238(7) Uani 1 1 d . . .
O3U O 0.6194(3) 0.47396(10) 0.07483(9) 0.0230(7) Uani 1 1 d . . .
C1U C 0.9094(4) 0.45152(15) 0.07243(12) 0.0149(8) Uani 1 1 d . . .
C2U C 1.0428(4) 0.44427(16) 0.04881(15) 0.0245(10) Uani 1 1 d . . .
H21U H 1.0483 0.4560 0.0197 0.029 Uiso 1 1 calc R . .
C3U C 1.1672(4) 0.42005(18) 0.06748(16) 0.0307(11) Uani 1 1 d . . .
H31U H 1.2590 0.4161 0.0513 0.037 Uiso 1 1 calc R . .
C4U C 1.1611(4) 0.40138(17) 0.10949(14) 0.0255(11) Uani 1 1 d . . .
C5U C 1.0259(5) 0.40737(17) 0.13174(14) 0.0290(11) Uani 1 1 d . . .
H51U H 1.0188 0.3941 0.1604 0.035 Uiso 1 1 calc R . .
C6U C 0.8996(4) 0.43209(17) 0.11388(14) 0.0254(10) Uani 1 1 d . . .
H61U H 0.8076 0.4356 0.1300 0.031 Uiso 1 1 calc R . .
C7U C 1.2997(5) 0.3758(2) 0.13030(17) 0.0487(15) Uani 1 1 d . . .
H71U H 1.3831 0.4013 0.1324 0.073 Uiso 1 1 calc R . .
H72U H 1.3330 0.3462 0.1126 0.073 Uiso 1 1 calc R . .
H73U H 1.2724 0.3635 0.1593 0.073 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 N11 2.072(3) . ?
Ni1 O2W 2.072(2) . ?
Ni1 N4 2.087(3) . ?
Ni1 O1W 2.100(2) . ?
Ni1 N1 2.217(3) . ?
Ni1 N8 2.254(3) . ?
O1W H21W 0.9293 . ?
O1W H22W 0.8857 . ?
O2W H11W 0.8294 . ?
O2W H12W 0.9659 . ?
N1 C15 1.493(4) . ?
N1 C2 1.498(5) . ?
N1 C14 1.503(5) . ?
C2 C3 1.508(5) . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
C3 N4 1.479(5) . ?
C3 H31 0.9900 . ?
C3 H32 0.9900 . ?
N4 C5 1.485(5) . ?
N4 H41 0.9300 . ?
C5 C6 1.501(6) . ?
C5 H51 0.9900 . ?
C5 H52 0.9900 . ?
C6 C7 1.518(6) . ?
C6 H61 0.9900 . ?
C6 H62 0.9900 . ?
C7 N8 1.494(5) . ?
C7 H71 0.9900 . ?
C7 H72 0.9900 . ?
N8 C17 1.484(5) . ?
N8 C9 1.496(4) . ?
C9 C10 1.505(5) . ?
C9 H91 0.9900 . ?
C9 H92 0.9900 . ?
C10 N11 1.473(5) . ?
C10 H101 0.9900 . ?
C10 H102 0.9900 . ?
N11 C12 1.480(5) . ?
N11 H111 0.9300 . ?
C12 C13 1.507(6) . ?
C12 H121 0.9900 . ?
C12 H122 0.9900 . ?
C13 C14 1.525(5) . ?
C13 H131 0.9900 . ?
C13 H132 0.9900 . ?
C14 H141 0.9900 . ?
C14 H142 0.9900 . ?
C15 C16 1.503(6) . ?
C15 H151 0.9900 . ?
C15 H152 0.9900 . ?
C16 F163 1.333(5) . ?
C16 F161 1.345(4) . ?
C16 F162 1.350(5) . ?
C17 C18 1.513(6) . ?
C17 H171 0.9900 . ?
C17 H172 0.9900 . ?
C18 F183 1.328(5) . ?
C18 F181 1.337(5) . ?
C18 F182 1.349(5) . ?
S1T O2T 1.452(3) . ?
S1T O3T 1.455(2) . ?
S1T O1T 1.457(3) . ?
S1T C1T 1.776(4) . ?
C1T C6T 1.384(5) . ?
C1T C2T 1.387(5) . ?
C2T C3T 1.371(5) . ?
C2T H21T 0.9500 . ?
C3T C4T 1.391(6) . ?
C3T H31T 0.9500 . ?
C4T C5T 1.369(6) . ?
C4T C7T 1.525(5) . ?
C5T C6T 1.395(5) . ?
C5T H51T 0.9500 . ?
C6T H61T 0.9500 . ?
C7T H71T 0.9800 . ?
C7T H72T 0.9800 . ?
C7T H73T 0.9800 . ?
S1U O2U 1.446(3) . ?
S1U O1U 1.456(3) . ?
S1U O3U 1.458(3) . ?
S1U C1U 1.771(4) . ?
C1U C6U 1.378(5) . ?
C1U C2U 1.387(5) . ?
C2U C3U 1.377(6) . ?
C2U H21U 0.9500 . ?
C3U C4U 1.385(6) . ?
C3U H31U 0.9500 . ?
C4U C5U 1.374(6) . ?
C4U C7U 1.518(6) . ?
C5U C6U 1.385(5) . ?
C5U H51U 0.9500 . ?
C6U H61U 0.9500 . ?
C7U H71U 0.9800 . ?
C7U H72U 0.9800 . ?
C7U H73U 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N11 Ni1 O2W 88.60(11) . . ?
N11 Ni1 N4 96.01(11) . . ?
O2W Ni1 N4 172.01(11) . . ?
N11 Ni1 O1W 167.73(12) . . ?
O2W Ni1 O1W 84.01(9) . . ?
N4 Ni1 O1W 92.50(10) . . ?
N11 Ni1 N1 92.25(11) . . ?
O2W Ni1 N1 90.09(11) . . ?
N4 Ni1 N1 83.23(12) . . ?
O1W Ni1 N1 97.53(10) . . ?
N11 Ni1 N8 82.91(11) . . ?
O2W Ni1 N8 96.38(11) . . ?
N4 Ni1 N8 90.67(12) . . ?
O1W Ni1 N8 88.17(10) . . ?
N1 Ni1 N8 171.80(11) . . ?
Ni1 O1W H21W 125.6 . . ?
Ni1 O1W H22W 109.8 . . ?
H21W O1W H22W 110.3 . . ?
Ni1 O2W H11W 129.7 . . ?
Ni1 O2W H12W 133.1 . . ?
H11W O2W H12W 94.7 . . ?
C15 N1 C2 110.8(3) . . ?
C15 N1 C14 109.4(3) . . ?
C2 N1 C14 110.6(3) . . ?
C15 N1 Ni1 107.9(2) . . ?
C2 N1 Ni1 104.0(2) . . ?
C14 N1 Ni1 114.0(2) . . ?
N1 C2 C3 110.1(3) . . ?
N1 C2 H21 109.6 . . ?
C3 C2 H21 109.6 . . ?
N1 C2 H22 109.6 . . ?
C3 C2 H22 109.6 . . ?
H21 C2 H22 108.2 . . ?
N4 C3 C2 109.4(3) . . ?
N4 C3 H31 109.8 . . ?
C2 C3 H31 109.8 . . ?
N4 C3 H32 109.8 . . ?
C2 C3 H32 109.8 . . ?
H31 C3 H32 108.3 . . ?
C3 N4 C5 110.6(3) . . ?
C3 N4 Ni1 107.4(2) . . ?
C5 N4 Ni1 119.1(2) . . ?
C3 N4 H41 106.3 . . ?
C5 N4 H41 106.3 . . ?
Ni1 N4 H41 106.3 . . ?
N4 C5 C6 111.8(3) . . ?
N4 C5 H51 109.2 . . ?
C6 C5 H51 109.2 . . ?
N4 C5 H52 109.2 . . ?
C6 C5 H52 109.2 . . ?
H51 C5 H52 107.9 . . ?
C5 C6 C7 116.5(3) . . ?
C5 C6 H61 108.2 . . ?
C7 C6 H61 108.2 . . ?
C5 C6 H62 108.2 . . ?
C7 C6 H62 108.2 . . ?
H61 C6 H62 107.3 . . ?
N8 C7 C6 116.4(3) . . ?
N8 C7 H71 108.2 . . ?
C6 C7 H71 108.2 . . ?
N8 C7 H72 108.2 . . ?
C6 C7 H72 108.2 . . ?
H71 C7 H72 107.3 . . ?
C17 N8 C7 109.5(3) . . ?
C17 N8 C9 110.9(3) . . ?
C7 N8 C9 111.8(3) . . ?
C17 N8 Ni1 107.5(2) . . ?
C7 N8 Ni1 114.1(2) . . ?
C9 N8 Ni1 102.8(2) . . ?
N8 C9 C10 110.6(3) . . ?
N8 C9 H91 109.5 . . ?
C10 C9 H91 109.5 . . ?
N8 C9 H92 109.5 . . ?
C10 C9 H92 109.5 . . ?
H91 C9 H92 108.1 . . ?
N11 C10 C9 108.9(3) . . ?
N11 C10 H101 109.9 . . ?
C9 C10 H101 109.9 . . ?
N11 C10 H102 109.9 . . ?
C9 C10 H102 109.9 . . ?
H101 C10 H102 108.3 . . ?
C10 N11 C12 110.9(3) . . ?
C10 N11 Ni1 107.7(2) . . ?
C12 N11 Ni1 117.6(2) . . ?
C10 N11 H111 106.7 . . ?
C12 N11 H111 106.7 . . ?
Ni1 N11 H111 106.7 . . ?
N11 C12 C13 112.6(3) . . ?
N11 C12 H121 109.1 . . ?
C13 C12 H121 109.1 . . ?
N11 C12 H122 109.1 . . ?
C13 C12 H122 109.1 . . ?
H121 C12 H122 107.8 . . ?
C12 C13 C14 116.1(3) . . ?
C12 C13 H131 108.3 . . ?
C14 C13 H131 108.3 . . ?
C12 C13 H132 108.3 . . ?
C14 C13 H132 108.3 . . ?
H131 C13 H132 107.4 . . ?
N1 C14 C13 115.3(3) . . ?
N1 C14 H141 108.5 . . ?
C13 C14 H141 108.5 . . ?
N1 C14 H142 108.5 . . ?
C13 C14 H142 108.5 . . ?
H141 C14 H142 107.5 . . ?
N1 C15 C16 119.7(3) . . ?
N1 C15 H151 107.4 . . ?
C16 C15 H151 107.4 . . ?
N1 C15 H152 107.4 . . ?
C16 C15 H152 107.4 . . ?
H151 C15 H152 106.9 . . ?
F163 C16 F161 107.2(3) . . ?
F163 C16 F162 106.0(3) . . ?
F161 C16 F162 105.2(3) . . ?
F163 C16 C15 115.7(3) . . ?
F161 C16 C15 108.9(3) . . ?
F162 C16 C15 113.1(3) . . ?
N8 C17 C18 118.9(3) . . ?
N8 C17 H171 107.6 . . ?
C18 C17 H171 107.6 . . ?
N8 C17 H172 107.6 . . ?
C18 C17 H172 107.6 . . ?
H171 C17 H172 107.0 . . ?
F183 C18 F181 107.0(4) . . ?
F183 C18 F182 106.4(4) . . ?
F181 C18 F182 104.8(3) . . ?
F183 C18 C17 115.6(4) . . ?
F181 C18 C17 109.2(4) . . ?
F182 C18 C17 113.0(4) . . ?
O2T S1T O3T 113.90(18) . . ?
O2T S1T O1T 112.79(17) . . ?
O3T S1T O1T 110.84(17) . . ?
O2T S1T C1T 107.15(18) . . ?
O3T S1T C1T 105.59(16) . . ?
O1T S1T C1T 105.90(17) . . ?
C6T C1T C2T 119.9(3) . . ?
C6T C1T S1T 120.6(3) . . ?
C2T C1T S1T 119.5(3) . . ?
C3T C2T C1T 119.9(4) . . ?
C3T C2T H21T 120.1 . . ?
C1T C2T H21T 120.1 . . ?
C2T C3T C4T 120.9(4) . . ?
C2T C3T H31T 119.5 . . ?
C4T C3T H31T 119.5 . . ?
C5T C4T C3T 119.1(4) . . ?
C5T C4T C7T 120.4(4) . . ?
C3T C4T C7T 120.5(4) . . ?
C4T C5T C6T 120.8(4) . . ?
C4T C5T H51T 119.6 . . ?
C6T C5T H51T 119.6 . . ?
C1T C6T C5T 119.5(4) . . ?
C1T C6T H61T 120.3 . . ?
C5T C6T H61T 120.3 . . ?
C4T C7T H71T 109.5 . . ?
C4T C7T H72T 109.5 . . ?
H71T C7T H72T 109.5 . . ?
C4T C7T H73T 109.5 . . ?
H71T C7T H73T 109.5 . . ?
H72T C7T H73T 109.5 . . ?
O2U S1U O1U 111.73(17) . . ?
O2U S1U O3U 113.98(16) . . ?
O1U S1U O3U 111.73(16) . . ?
O2U S1U C1U 105.08(16) . . ?
O1U S1U C1U 107.07(16) . . ?
O3U S1U C1U 106.63(17) . . ?
C6U C1U C2U 119.6(4) . . ?
C6U C1U S1U 120.6(3) . . ?
C2U C1U S1U 119.8(3) . . ?
C3U C2U C1U 120.1(4) . . ?
C3U C2U H21U 120.0 . . ?
C1U C2U H21U 120.0 . . ?
C2U C3U C4U 121.2(4) . . ?
C2U C3U H31U 119.4 . . ?
C4U C3U H31U 119.4 . . ?
C5U C4U C3U 117.7(4) . . ?
C5U C4U C7U 121.3(4) . . ?
C3U C4U C7U 121.0(4) . . ?
C4U C5U C6U 122.3(4) . . ?
C4U C5U H51U 118.9 . . ?
C6U C5U H51U 118.9 . . ?
C1U C6U C5U 119.1(4) . . ?
C1U C6U H61U 120.4 . . ?
C5U C6U H61U 120.4 . . ?
C4U C7U H71U 109.5 . . ?
C4U C7U H72U 109.5 . . ?
H71U C7U H72U 109.5 . . ?
C4U C7U H73U 109.5 . . ?
H71U C7U H73U 109.5 . . ?
H72U C7U H73U 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.689
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.093
####################################################################### 
# 
# 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_tfe2cam
_database_code_depnum_ccdc_archive 'CCDC 1430241'
_audit_update_record             
;
2015-10-08 deposited with the CCDC.
2015-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H28 F6 N4, 2(Cl), 2(H2 O)'
_chemical_formula_sum            'C14 H32 Cl2 F6 N4 O2'
_chemical_formula_weight         473.34
_chemical_compound_source        'synthesized by the authors'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   9.5863(6)
_cell_length_b                   9.4059(7)
_cell_length_c                   11.7418(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.367(2)
_cell_angle_gamma                90.00
_cell_volume                     1020.88(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9378
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      27.52

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.516
_exptl_crystal_size_mid          0.394
_exptl_crystal_size_min          0.311
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.390
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13320
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_sigmaI/netI    0.0113
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.45
_diffrn_reflns_theta_max         27.49
_reflns_number_total             2354
_reflns_number_gt                2157
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0325P)²+0.8844P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2354
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0814
_refine_ls_wR_factor_gt          0.0787
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.15441(12) 0.64360(12) 0.42918(10) 0.0156(2) Uani 1 1 d . . .
C2 C 0.03104(15) 0.73406(15) 0.36971(12) 0.0179(3) Uani 1 1 d . . .
H21 H -0.0318 0.6806 0.3030 0.021 Uiso 1 1 calc R . .
H22 H 0.0678 0.8188 0.3369 0.021 Uiso 1 1 calc R . .
C3 C -0.05858(15) 0.78237(14) 0.45164(12) 0.0178(3) Uani 1 1 d . . .
H31 H 0.0041 0.8334 0.5200 0.021 Uiso 1 1 calc R . .
H32 H -0.1348 0.8488 0.4091 0.021 Uiso 1 1 calc R . .
N4 N -0.12686(12) 0.65778(12) 0.49434(10) 0.0154(2) Uani 1 1 d . . .
H41 H -0.0550 0.5969 0.5335 0.018 Uiso 1 1 calc R . .
H42 H -0.1828 0.6099 0.4300 0.018 Uiso 1 1 calc R . .
C5 C -0.21887(15) 0.69543(15) 0.57463(13) 0.0190(3) Uani 1 1 d . . .
H51 H -0.2880 0.7709 0.5375 0.023 Uiso 1 1 calc R . .
H52 H -0.1567 0.7334 0.6497 0.023 Uiso 1 1 calc R . .
C6 C -0.30232(15) 0.56721(16) 0.60082(13) 0.0212(3) Uani 1 1 d . . .
H61 H -0.3704 0.5360 0.5260 0.025 Uiso 1 1 calc R . .
H62 H -0.3608 0.5979 0.6544 0.025 Uiso 1 1 calc R . .
C7 C -0.21108(16) 0.43934(15) 0.65646(12) 0.0194(3) Uani 1 1 d . . .
H71 H -0.1286 0.4731 0.7208 0.023 Uiso 1 1 calc R . .
H72 H -0.2707 0.3761 0.6919 0.023 Uiso 1 1 calc R . .
C8 C 0.26492(15) 0.71599(15) 0.52021(12) 0.0172(3) Uani 1 1 d . . .
H81 H 0.3367 0.6438 0.5596 0.021 Uiso 1 1 calc R . .
H82 H 0.2180 0.7521 0.5801 0.021 Uiso 1 1 calc R . .
C9 C 0.34694(15) 0.83831(16) 0.48451(12) 0.0204(3) Uani 1 1 d . . .
F1 F 0.45112(11) 0.88352(12) 0.57660(9) 0.0377(3) Uani 1 1 d . . .
F2 F 0.26447(13) 0.95036(12) 0.44499(15) 0.0650(5) Uani 1 1 d . . .
F3 F 0.41203(15) 0.80671(15) 0.40174(11) 0.0600(4) Uani 1 1 d . . .
Cl1 Cl 0.87862(4) 0.08267(4) 0.23407(3) 0.02150(10) Uani 1 1 d . . .
O1W O 0.40453(11) 0.09257(11) 0.79596(9) 0.0222(2) Uani 1 1 d . . .
H11W H 0.3223 0.0539 0.7739 0.027 Uiso 1 1 d R . .
H12W H 0.3935 0.1772 0.7683 0.027 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
N1 C8 1.4588(17) . ?
N1 C2 1.4739(17) . ?
N1 C7 1.4848(17) 3_566 ?
C2 C3 1.5192(19) . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
C3 N4 1.4923(17) . ?
C3 H31 0.9900 . ?
C3 H32 0.9900 . ?
N4 C5 1.4944(16) . ?
N4 H41 0.9200 . ?
N4 H42 0.9200 . ?
C5 C6 1.523(2) . ?
C5 H51 0.9900 . ?
C5 H52 0.9900 . ?
C6 C7 1.528(2) . ?
C6 H61 0.9900 . ?
C6 H62 0.9900 . ?
C7 N1 1.4848(17) 3_566 ?
C7 H71 0.9900 . ?
C7 H72 0.9900 . ?
C8 C9 1.5140(19) . ?
C8 H81 0.9900 . ?
C8 H82 0.9900 . ?
C9 F3 1.3205(17) . ?
C9 F2 1.3254(18) . ?
C9 F1 1.3323(16) . ?
O1W H11W 0.8445 . ?
O1W H12W 0.8553 . ?

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
C8 N1 C2 114.42(11) . . ?
C8 N1 C7 114.61(11) . 3_566 ?
C2 N1 C7 111.97(10) . 3_566 ?
N1 C2 C3 112.96(11) . . ?
N1 C2 H21 109.0 . . ?
C3 C2 H21 109.0 . . ?
N1 C2 H22 109.0 . . ?
C3 C2 H22 109.0 . . ?
H21 C2 H22 107.8 . . ?
N4 C3 C2 110.48(11) . . ?
N4 C3 H31 109.6 . . ?
C2 C3 H31 109.6 . . ?
N4 C3 H32 109.6 . . ?
C2 C3 H32 109.6 . . ?
H31 C3 H32 108.1 . . ?
C3 N4 C5 114.24(11) . . ?
C3 N4 H41 108.7 . . ?
C5 N4 H41 108.7 . . ?
C3 N4 H42 108.7 . . ?
C5 N4 H42 108.7 . . ?
H41 N4 H42 107.6 . . ?
N4 C5 C6 111.66(11) . . ?
N4 C5 H51 109.3 . . ?
C6 C5 H51 109.3 . . ?
N4 C5 H52 109.3 . . ?
C6 C5 H52 109.3 . . ?
H51 C5 H52 107.9 . . ?
C5 C6 C7 115.96(11) . . ?
C5 C6 H61 108.3 . . ?
C7 C6 H61 108.3 . . ?
C5 C6 H62 108.3 . . ?
C7 C6 H62 108.3 . . ?
H61 C6 H62 107.4 . . ?
N1 C7 C6 113.25(11) 3_566 . ?
N1 C7 H71 108.9 3_566 . ?
C6 C7 H71 108.9 . . ?
N1 C7 H72 108.9 3_566 . ?
C6 C7 H72 108.9 . . ?
H71 C7 H72 107.7 . . ?
N1 C8 C9 118.78(11) . . ?
N1 C8 H81 107.6 . . ?
C9 C8 H81 107.6 . . ?
N1 C8 H82 107.6 . . ?
C9 C8 H82 107.6 . . ?
H81 C8 H82 107.1 . . ?
F3 C9 F2 106.00(15) . . ?
F3 C9 F1 105.68(12) . . ?
F2 C9 F1 106.24(13) . . ?
F3 C9 C8 114.46(12) . . ?
F2 C9 C8 113.32(12) . . ?
F1 C9 C8 110.52(11) . . ?
H11W O1W H12W 105.8 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.512
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_tfe2te2p-sq
_database_code_depnum_ccdc_archive 'CCDC 1430242'
_audit_update_record             
;
2015-10-08 deposited with the CCDC.
2015-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H36 F6 N4 O6 P2, 4(Br), 0.5 (H2 O)'
_chemical_formula_sum            'C16 H37 Br4 F6 N4 O6.50 P2'
_chemical_formula_weight         885.08
_chemical_compound_source        'synthesized by the authors'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   7.3372(2)
_cell_length_b                   11.5789(3)
_cell_length_c                   17.6946(4)
_cell_angle_alpha                85.4460(10)
_cell_angle_beta                 88.8250(10)
_cell_angle_gamma                80.9820(10)
_cell_volume                     1479.96(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9215
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      27.58

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.986
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             874
_exptl_absorpt_coefficient_mu    5.625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3170
_exptl_absorpt_correction_T_max  0.5970
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22437
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0313
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.15
_diffrn_reflns_theta_max         27.50
_reflns_number_total             6780
_reflns_number_gt                5621
_reflns_threshold_expression     >2sigma(I)

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.277 0.367 0.732 8 4 '0.5 (H2 O)'
2 0.722 0.633 0.268 8 4 '0.5 (H2 O)'
_platon_squeeze_details          
;
electronic maxima pointing to disordered solvate molecule, squeezed off
;

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          SQUEEZE

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0243P)²+0.5397P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6780
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0268
_refine_ls_wR_factor_ref         0.0581
_refine_ls_wR_factor_gt          0.0561
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1A N 0.7304(2) 0.26810(14) 0.06704(9) 0.0103(4) Uani 1 1 d . . .
H1A H 0.8077 0.2530 0.1089 0.012 Uiso 1 1 calc R . .
C2A C 0.5383(3) 0.30395(18) 0.09701(12) 0.0118(4) Uani 1 1 d . . .
H2A H 0.4946 0.2354 0.1244 0.014 Uiso 1 1 calc R . .
H2B H 0.4537 0.3319 0.0542 0.014 Uiso 1 1 calc R . .
C3A C 0.5362(3) 0.40106(18) 0.15036(12) 0.0129(4) Uani 1 1 d . . .
H3A H 0.6026 0.3685 0.1974 0.015 Uiso 1 1 calc R . .
H3B H 0.6024 0.4626 0.1260 0.015 Uiso 1 1 calc R . .
N4A N 0.3422(2) 0.45567(14) 0.17058(10) 0.0117(4) Uani 1 1 d . . .
H4A H 0.2846 0.3958 0.1936 0.014 Uiso 1 1 calc R . .
C5A C 0.2246(3) 0.50919(18) 0.10316(11) 0.0117(4) Uani 1 1 d . . .
H5A H 0.1003 0.5417 0.1216 0.014 Uiso 1 1 calc R . .
H5B H 0.2102 0.4466 0.0697 0.014 Uiso 1 1 calc R . .
C6A C 0.3059(3) 0.60580(19) 0.05717(12) 0.0188(5) Uani 1 1 d . . .
H6A H 0.2994 0.6753 0.0868 0.023 Uiso 1 1 calc R . .
H6B H 0.4370 0.5783 0.0450 0.023 Uiso 1 1 calc R . .
C7A C 0.1966(3) 0.63807(18) -0.01544(11) 0.0116(4) Uani 1 1 d . . .
H7A H 0.1997 0.5669 -0.0432 0.014 Uiso 1 1 calc R . .
H7B H 0.0663 0.6663 -0.0023 0.014 Uiso 1 1 calc R . .
C8A C 0.7444(3) 0.15555(17) 0.02924(12) 0.0155(5) Uani 1 1 d . . .
H8A H 0.8405 0.1549 -0.0109 0.019 Uiso 1 1 calc R . .
H8B H 0.6255 0.1532 0.0044 0.019 Uiso 1 1 calc R . .
P1A P 0.79977(8) 0.02408(5) 0.09301(3) 0.01452(13) Uani 1 1 d . . .
O11A O 0.6718(2) -0.05544(13) 0.06212(9) 0.0254(4) Uani 1 1 d . . .
H11A H 0.7183 -0.1398 0.0662 0.030 Uiso 1 1 d R . .
O12A O 0.7377(2) 0.05779(13) 0.17281(8) 0.0199(4) Uani 1 1 d . . .
H12A H 0.6204 0.0389 0.1909 0.024 Uiso 1 1 d R . .
O13A O 0.9993(2) -0.02104(14) 0.08931(9) 0.0233(4) Uani 1 1 d . . .
C9A C 0.3581(3) 0.53924(19) 0.22971(12) 0.0176(5) Uani 1 1 d . . .
H9A H 0.4130 0.6064 0.2062 0.021 Uiso 1 1 calc R . .
H9B H 0.4432 0.4991 0.2696 0.021 Uiso 1 1 calc R . .
C10A C 0.1762(4) 0.5852(2) 0.26603(13) 0.0254(6) Uani 1 1 d . . .
F1A F 0.2070(2) 0.61647(14) 0.33515(8) 0.0417(4) Uani 1 1 d . . .
F2A F 0.0641(2) 0.50523(13) 0.27358(8) 0.0359(4) Uani 1 1 d . . .
F3A F 0.0858(2) 0.67953(12) 0.22750(8) 0.0338(4) Uani 1 1 d . . .
N1X N 0.8605(2) 0.93789(14) 0.66532(9) 0.0113(4) Uani 1 1 d . . .
H1X H 0.8060 0.8774 0.6894 0.014 Uiso 1 1 calc R . .
C2X C 1.0530(3) 0.88574(18) 0.64185(12) 0.0132(4) Uani 1 1 d . . .
H2X H 1.1252 0.8546 0.6877 0.016 Uiso 1 1 calc R . .
H2Y H 1.1145 0.9482 0.6157 0.016 Uiso 1 1 calc R . .
C3X C 1.0525(3) 0.78797(18) 0.58966(12) 0.0135(5) Uani 1 1 d . . .
H3X H 1.0176 0.7182 0.6189 0.016 Uiso 1 1 calc R . .
H3Y H 0.9598 0.8135 0.5494 0.016 Uiso 1 1 calc R . .
N4X N 1.2403(2) 0.75616(15) 0.55397(10) 0.0122(4) Uani 1 1 d . . .
H4X H 1.3226 0.7309 0.5933 0.015 Uiso 1 1 calc R . .
C5X C 1.3128(3) 0.85660(18) 0.50858(12) 0.0133(4) Uani 1 1 d . . .
H5X H 1.3176 0.9209 0.5418 0.016 Uiso 1 1 calc R . .
H5Y H 1.4401 0.8292 0.4910 0.016 Uiso 1 1 calc R . .
C6X C 1.1932(3) 0.9031(2) 0.44056(13) 0.0240(6) Uani 1 1 d . . .
H6X H 1.1948 0.8406 0.4054 0.029 Uiso 1 1 calc R . .
H6Y H 1.0643 0.9266 0.4575 0.029 Uiso 1 1 calc R . .
C7X C 1.2637(3) 1.00783(18) 0.39974(12) 0.0128(4) Uani 1 1 d . . .
H7X H 1.2710 1.0675 0.4362 0.015 Uiso 1 1 calc R . .
H7Y H 1.3896 0.9827 0.3799 0.015 Uiso 1 1 calc R . .
C8X C 0.8815(3) 1.02250(18) 0.72394(12) 0.0149(5) Uani 1 1 d . . .
H8X H 0.9386 1.0881 0.6995 0.018 Uiso 1 1 calc R . .
H8Y H 0.9669 0.9818 0.7636 0.018 Uiso 1 1 calc R . .
P1X P 0.66753(8) 1.08174(5) 0.76846(3) 0.01838(13) Uani 1 1 d . . .
O11X O 0.5789(3) 1.19357(15) 0.72090(10) 0.0415(5) Uani 1 1 d . . .
H11X H 0.6351 1.2386 0.7158 0.050 Uiso 1 1 d R . .
O12X O 0.7258(2) 1.12562(14) 0.84238(9) 0.0255(4) Uani 1 1 d . . .
H12X H 0.8206 1.0661 0.8632 0.031 Uiso 1 1 d R . .
O13X O 0.5507(2) 0.98819(15) 0.77373(10) 0.0280(4) Uani 1 1 d . . .
C9X C 1.2448(3) 0.65590(18) 0.50531(12) 0.0169(5) Uani 1 1 d . . .
H9X H 1.3577 0.6509 0.4733 0.020 Uiso 1 1 calc R . .
H9Y H 1.1374 0.6726 0.4710 0.020 Uiso 1 1 calc R . .
C10X C 1.2419(3) 0.5386(2) 0.54847(13) 0.0220(5) Uani 1 1 d . . .
F1X F 1.0756(2) 0.52480(12) 0.57550(8) 0.0331(4) Uani 1 1 d . . .
F2X F 1.2917(2) 0.45466(12) 0.50165(9) 0.0350(4) Uani 1 1 d . . .
F3X F 1.3575(2) 0.52027(13) 0.60580(10) 0.0500(5) Uani 1 1 d . . .
Br1 Br 0.43168(3) 0.26391(2) 0.332239(13) 0.02210(7) Uani 1 1 d . . .
Br2 Br 0.05263(3) 0.26515(2) 0.184160(13) 0.02392(7) Uani 1 1 d . . .
Br3 Br 0.75390(3) 0.672087(18) 0.085456(14) 0.01954(6) Uani 1 1 d . . .
Br4 Br 0.75314(3) 0.83162(2) 0.405796(15) 0.02883(7) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1A C8A 1.500(3) . ?
N1A C2A 1.504(3) . ?
N1A C7A 1.518(2) 2_665 ?
N1A H1A 0.9300 . ?
C2A C3A 1.523(3) . ?
C2A H2A 0.9900 . ?
C2A H2B 0.9900 . ?
C3A N4A 1.513(3) . ?
C3A H3A 0.9900 . ?
C3A H3B 0.9900 . ?
N4A C9A 1.499(3) . ?
N4A C5A 1.519(3) . ?
N4A H4A 0.9300 . ?
C5A C6A 1.521(3) . ?
C5A H5A 0.9900 . ?
C5A H5B 0.9900 . ?
C6A C7A 1.518(3) . ?
C6A H6A 0.9900 . ?
C6A H6B 0.9900 . ?
C7A N1A 1.518(2) 2_665 ?
C7A H7A 0.9900 . ?
C7A H7B 0.9900 . ?
C8A P1A 1.819(2) . ?
C8A H8A 0.9900 . ?
C8A H8B 0.9900 . ?
P1A O13A 1.4769(17) . ?
P1A O12A 1.5360(16) . ?
P1A O11A 1.5490(15) . ?
O11A H11A 0.9801 . ?
O12A H12A 0.9636 . ?
C9A C10A 1.508(3) . ?
C9A H9A 0.9900 . ?
C9A H9B 0.9900 . ?
C10A F2A 1.328(3) . ?
C10A F3A 1.331(3) . ?
C10A F1A 1.336(3) . ?
N1X C8X 1.508(3) . ?
N1X C2X 1.511(3) . ?
N1X C7X 1.516(3) 2_776 ?
N1X H1X 0.9300 . ?
C2X C3X 1.517(3) . ?
C2X H2X 0.9900 . ?
C2X H2Y 0.9900 . ?
C3X N4X 1.508(3) . ?
C3X H3X 0.9900 . ?
C3X H3Y 0.9900 . ?
N4X C9X 1.495(3) . ?
N4X C5X 1.519(3) . ?
N4X H4X 0.9300 . ?
C5X C6X 1.517(3) . ?
C5X H5X 0.9900 . ?
C5X H5Y 0.9900 . ?
C6X C7X 1.517(3) . ?
C6X H6X 0.9900 . ?
C6X H6Y 0.9900 . ?
C7X N1X 1.516(3) 2_776 ?
C7X H7X 0.9900 . ?
C7X H7Y 0.9900 . ?
C8X P1X 1.804(2) . ?
C8X H8X 0.9900 . ?
C8X H8Y 0.9900 . ?
P1X O13X 1.4794(17) . ?
P1X O12X 1.5326(17) . ?
P1X O11X 1.5469(18) . ?
O11X H11X 0.7132 . ?
O12X H12X 0.9560 . ?
C9X C10X 1.507(3) . ?
C9X H9X 0.9900 . ?
C9X H9Y 0.9900 . ?
C10X F3X 1.318(3) . ?
C10X F1X 1.330(3) . ?
C10X F2X 1.330(3) . ?

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
C8A N1A C2A 110.82(15) . . ?
C8A N1A C7A 110.95(16) . 2_665 ?
C2A N1A C7A 114.45(16) . 2_665 ?
C8A N1A H1A 106.7 . . ?
C2A N1A H1A 106.7 . . ?
C7A N1A H1A 106.7 2_665 . ?
N1A C2A C3A 110.19(16) . . ?
N1A C2A H2A 109.6 . . ?
C3A C2A H2A 109.6 . . ?
N1A C2A H2B 109.6 . . ?
C3A C2A H2B 109.6 . . ?
H2A C2A H2B 108.1 . . ?
N4A C3A C2A 112.19(16) . . ?
N4A C3A H3A 109.2 . . ?
C2A C3A H3A 109.2 . . ?
N4A C3A H3B 109.2 . . ?
C2A C3A H3B 109.2 . . ?
H3A C3A H3B 107.9 . . ?
C9A N4A C3A 107.07(16) . . ?
C9A N4A C5A 114.12(16) . . ?
C3A N4A C5A 114.57(16) . . ?
C9A N4A H4A 106.9 . . ?
C3A N4A H4A 106.9 . . ?
C5A N4A H4A 106.9 . . ?
N4A C5A C6A 113.19(16) . . ?
N4A C5A H5A 108.9 . . ?
C6A C5A H5A 108.9 . . ?
N4A C5A H5B 108.9 . . ?
C6A C5A H5B 108.9 . . ?
H5A C5A H5B 107.8 . . ?
C7A C6A C5A 108.67(17) . . ?
C7A C6A H6A 110.0 . . ?
C5A C6A H6A 110.0 . . ?
C7A C6A H6B 110.0 . . ?
C5A C6A H6B 110.0 . . ?
H6A C6A H6B 108.3 . . ?
N1A C7A C6A 113.20(16) 2_665 . ?
N1A C7A H7A 108.9 2_665 . ?
C6A C7A H7A 108.9 . . ?
N1A C7A H7B 108.9 2_665 . ?
C6A C7A H7B 108.9 . . ?
H7A C7A H7B 107.8 . . ?
N1A C8A P1A 114.33(14) . . ?
N1A C8A H8A 108.7 . . ?
P1A C8A H8A 108.7 . . ?
N1A C8A H8B 108.7 . . ?
P1A C8A H8B 108.7 . . ?
H8A C8A H8B 107.6 . . ?
O13A P1A O12A 112.10(9) . . ?
O13A P1A O11A 115.35(10) . . ?
O12A P1A O11A 110.62(9) . . ?
O13A P1A C8A 110.21(10) . . ?
O12A P1A C8A 106.92(9) . . ?
O11A P1A C8A 100.76(9) . . ?
P1A O11A H11A 116.0 . . ?
P1A O12A H12A 117.3 . . ?
N4A C9A C10A 113.59(18) . . ?
N4A C9A H9A 108.8 . . ?
C10A C9A H9A 108.8 . . ?
N4A C9A H9B 108.8 . . ?
C10A C9A H9B 108.8 . . ?
H9A C9A H9B 107.7 . . ?
F2A C10A F3A 107.5(2) . . ?
F2A C10A F1A 107.84(19) . . ?
F3A C10A F1A 107.00(19) . . ?
F2A C10A C9A 112.30(19) . . ?
F3A C10A C9A 112.9(2) . . ?
F1A C10A C9A 109.1(2) . . ?
C8X N1X C2X 106.70(15) . . ?
C8X N1X C7X 113.31(16) . 2_776 ?
C2X N1X C7X 114.62(16) . 2_776 ?
C8X N1X H1X 107.3 . . ?
C2X N1X H1X 107.3 . . ?
C7X N1X H1X 107.3 2_776 . ?
N1X C2X C3X 112.20(16) . . ?
N1X C2X H2X 109.2 . . ?
C3X C2X H2X 109.2 . . ?
N1X C2X H2Y 109.2 . . ?
C3X C2X H2Y 109.2 . . ?
H2X C2X H2Y 107.9 . . ?
N4X C3X C2X 110.69(16) . . ?
N4X C3X H3X 109.5 . . ?
C2X C3X H3X 109.5 . . ?
N4X C3X H3Y 109.5 . . ?
C2X C3X H3Y 109.5 . . ?
H3X C3X H3Y 108.1 . . ?
C9X N4X C3X 111.42(16) . . ?
C9X N4X C5X 109.19(16) . . ?
C3X N4X C5X 114.99(16) . . ?
C9X N4X H4X 106.9 . . ?
C3X N4X H4X 106.9 . . ?
C5X N4X H4X 106.9 . . ?
C6X C5X N4X 112.10(17) . . ?
C6X C5X H5X 109.2 . . ?
N4X C5X H5X 109.2 . . ?
C6X C5X H5Y 109.2 . . ?
N4X C5X H5Y 109.2 . . ?
H5X C5X H5Y 107.9 . . ?
C7X C6X C5X 110.34(17) . . ?
C7X C6X H6X 109.6 . . ?
C5X C6X H6X 109.6 . . ?
C7X C6X H6Y 109.6 . . ?
C5X C6X H6Y 109.6 . . ?
H6X C6X H6Y 108.1 . . ?
N1X C7X C6X 111.84(16) 2_776 . ?
N1X C7X H7X 109.2 2_776 . ?
C6X C7X H7X 109.2 . . ?
N1X C7X H7Y 109.2 2_776 . ?
C6X C7X H7Y 109.2 . . ?
H7X C7X H7Y 107.9 . . ?
N1X C8X P1X 114.05(14) . . ?
N1X C8X H8X 108.7 . . ?
P1X C8X H8X 108.7 . . ?
N1X C8X H8Y 108.7 . . ?
P1X C8X H8Y 108.7 . . ?
H8X C8X H8Y 107.6 . . ?
O13X P1X O12X 118.07(10) . . ?
O13X P1X O11X 112.94(11) . . ?
O12X P1X O11X 104.91(10) . . ?
O13X P1X C8X 106.80(10) . . ?
O12X P1X C8X 104.58(10) . . ?
O11X P1X C8X 109.02(11) . . ?
P1X O11X H11X 114.8 . . ?
P1X O12X H12X 106.0 . . ?
N4X C9X C10X 114.61(18) . . ?
N4X C9X H9X 108.6 . . ?
C10X C9X H9X 108.6 . . ?
N4X C9X H9Y 108.6 . . ?
C10X C9X H9Y 108.6 . . ?
H9X C9X H9Y 107.6 . . ?
F3X C10X F1X 107.7(2) . . ?
F3X C10X F2X 107.8(2) . . ?
F1X C10X F2X 106.83(18) . . ?
F3X C10X C9X 112.35(19) . . ?
F1X C10X C9X 113.2(2) . . ?
F2X C10X C9X 108.67(19) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.538
_refine_diff_density_min         -1.128
_refine_diff_density_rms         0.090
