#------------------------------------------------------------------------------
#$Date: 2018-05-17 23:48:01 +0300 (Thu, 17 May 2018) $
#$Revision: 207836 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/35/4033562.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4033562
loop_
_publ_author_name
'Illán-Cabeza, Nuria A'
'Jiménez-Pulido, Sonia B'
'Hueso-Ureña, Francisco'
'Ramírez-Expósito, María J'
'Sánchez-Sánchez, Purificación'
'Martínez-Martos, José M'
'Moreno-Carretero, Miguel N'
_publ_section_title
;
 Effects on estrogen-dependent and triple negative breast cancer cells
 growth of Ni(II), Zn(II) and Cd(II) complexes with the Schiff base
 derived from pyridine-2-carboxaldehyde and 5,6-diamino-1,3-dimethyluracil
 explored through the renin-angiotensin system (RAS)-regulating
 aminopeptidases.
;
_journal_name_full               'Journal of inorganic biochemistry'
_journal_page_first              52
_journal_page_last               62
_journal_paper_doi               10.1016/j.jinorgbio.2018.04.022
_journal_volume                  185
_journal_year                    2018
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C24 H24 N10 Ni1 O5'
_chemical_formula_sum            'C24 H24 N10 Ni O5'
_chemical_formula_weight         591.24
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2017-01-12T12:33:53-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                116.489(8)
_cell_angle_beta                 110.082(12)
_cell_angle_gamma                94.251(10)
_cell_formula_units_Z            2
_cell_length_a                   9.7652(10)
_cell_length_b                   12.6071(15)
_cell_length_c                   12.6665(16)
_cell_measurement_reflns_used    76
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      3
_cell_measurement_wavelength     0.71073
_cell_volume                     1262.0(3)
_computing_cell_refinement
'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      0.01
_diffrn_orient_matrix_UB_12      0
_diffrn_orient_matrix_UB_13      0
_diffrn_orient_matrix_UB_21      0
_diffrn_orient_matrix_UB_22      0.01
_diffrn_orient_matrix_UB_23      0
_diffrn_orient_matrix_UB_31      0
_diffrn_orient_matrix_UB_32      0
_diffrn_orient_matrix_UB_33      0.01
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0823
_diffrn_reflns_av_unetI/netI     0.06
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            34682
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         5.043
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.827
_exptl_absorpt_correction_T_max  0.879
_exptl_absorpt_correction_T_min  0.7022
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2.10 (Sheldrick, 2003)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.79
_refine_diff_density_min         -0.957
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     381
_refine_ls_number_reflns         5754
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0958
_refine_ls_R_factor_gt           0.0597
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1010P)²+1.0087P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1485
_refine_ls_wR_factor_ref         0.1756
_reflns_Friedel_coverage         0
_reflns_number_gt                4087
_reflns_number_total             5754
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            archive_Ni10344.cif
_cod_data_source_block           shelx
_cod_database_code               4033562
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.18176(5) 0.16083(4) 0.82962(4) 0.02511(17) Uani 1 1 d . . . . .
O42 O 0.2153(3) 0.4423(2) 1.2610(2) 0.0303(5) Uani 1 1 d . . . . .
O41 O 0.2763(3) -0.0451(2) 0.4417(2) 0.0306(6) Uani 1 1 d . . . . .
O22 O -0.2584(3) 0.4481(2) 1.0424(3) 0.0363(6) Uani 1 1 d . . . . .
O21 O 0.4721(3) 0.3414(2) 0.5425(3) 0.0385(6) Uani 1 1 d . . . . .
N11 N 0.3822(3) 0.3215(3) 0.6761(3) 0.0277(6) Uani 1 1 d . . . . .
OW O 0.3538(4) 0.5539(3) 0.5575(3) 0.0556(8) Uani 1 1 d . . . . .
N31 N 0.3749(3) 0.1491(3) 0.4925(3) 0.0295(6) Uani 1 1 d . . . . .
N52 N 0.2146(3) 0.2644(2) 1.0174(3) 0.0245(6) Uani 1 1 d . . . . .
N12 N -0.1464(3) 0.3284(3) 0.9237(3) 0.0286(6) Uani 1 1 d . . . . .
N1F2 N 0.3958(3) 0.1433(2) 0.9305(3) 0.0260(6) Uani 1 1 d . . . . .
N1F1 N 0.0647(3) -0.0156(3) 0.7742(3) 0.0252(6) Uani 1 1 d . . . . .
C4F2 C 0.6809(4) 0.1660(4) 1.0960(4) 0.0360(9) Uani 1 1 d . . . . .
H4F2 H 0.779652 0.173828 1.152822 0.043 Uiso 1 1 calc R U . . .
N32 N -0.0204(3) 0.4482(3) 1.1506(3) 0.0309(7) Uani 1 1 d . . . . .
N51 N 0.1843(3) 0.0553(3) 0.6533(3) 0.0250(6) Uani 1 1 d . . . . .
C5F1 C -0.0875(4) -0.1655(3) 0.7813(4) 0.0327(8) Uani 1 1 d . . . . .
H5F1 H -0.136625 -0.184313 0.8263 0.039 Uiso 1 1 calc R U . . .
N62 N -0.0175(4) 0.2112(3) 0.8054(3) 0.0288(6) Uani 1 1 d . . . . .
N61 N 0.2830(3) 0.2934(3) 0.8095(3) 0.0275(6) Uani 1 1 d . . . . .
C42 C 0.1082(4) 0.4040(3) 1.1552(3) 0.0277(7) Uani 1 1 d . . . . .
C52 C 0.1016(4) 0.3183(3) 1.0340(3) 0.0246(7) Uani 1 1 d . . . . .
C3F1 C -0.0262(4) -0.2239(3) 0.6017(4) 0.0330(8) Uani 1 1 d . . . . .
H3F1 H -0.03212 -0.284701 0.520241 0.04 Uiso 1 1 calc R U . . .
C3F2 C 0.5864(4) 0.2250(3) 1.1457(4) 0.0318(8) Uani 1 1 d . . . . .
H3F2 H 0.618869 0.273957 1.237024 0.038 Uiso 1 1 calc R U . . .
C2F2 C 0.4432(4) 0.2122(3) 1.0610(3) 0.0254(7) Uani 1 1 d . . . . .
C512 C 0.3391(4) 0.2742(3) 1.1056(3) 0.0254(7) Uani 1 1 d . . . . .
C31 C 0.4161(5) 0.1007(4) 0.3835(4) 0.0372(9) Uani 1 1 d . . . . .
H31A H 0.418491 0.160153 0.3537 0.056 Uiso 1 1 calc R U . . .
H31B H 0.341367 0.022961 0.312361 0.056 Uiso 1 1 calc R U . . .
H31C H 0.516393 0.086415 0.41095 0.056 Uiso 1 1 calc R U . . .
C61 C 0.3085(4) 0.2494(3) 0.7072(3) 0.0246(7) Uani 1 1 d . . . . .
C12 C -0.2809(4) 0.2912(4) 0.8052(3) 0.0359(9) Uani 1 1 d . . . . .
H12A H -0.36594 0.311611 0.827183 0.054 Uiso 1 1 calc R U . . .
H12B H -0.30593 0.202294 0.746546 0.054 Uiso 1 1 calc R U . . .
H12C H -0.261229 0.334843 0.762092 0.054 Uiso 1 1 calc R U . . .
C511 C 0.1265(4) -0.0616(3) 0.5958(3) 0.0278(7) Uani 1 1 d . . . . .
C11 C 0.4451(4) 0.4537(3) 0.7684(4) 0.0350(8) Uani 1 1 d . . . . .
H11A H 0.515818 0.488219 0.745276 0.053 Uiso 1 1 calc R U . . .
H11B H 0.498727 0.467516 0.856433 0.053 Uiso 1 1 calc R U . . .
H11C H 0.362839 0.493946 0.765302 0.053 Uiso 1 1 calc R U . . .
C51 C 0.2613(4) 0.1188(3) 0.6190(3) 0.0257(7) Uani 1 1 d . . . . .
C41 C 0.3010(4) 0.0665(3) 0.5142(3) 0.0253(7) Uani 1 1 d . . . . .
C6F1 C -0.0057(4) -0.0467(3) 0.8319(4) 0.0303(8) Uani 1 1 d . . . . .
H6F1 H -0.000232 0.015563 0.912457 0.036 Uiso 1 1 calc R U . . .
C2F1 C 0.0529(4) -0.1030(3) 0.6574(3) 0.0274(7) Uani 1 1 d . . . . .
C21 C 0.4128(4) 0.2750(3) 0.5687(3) 0.0298(8) Uani 1 1 d . . . . .
C4F1 C -0.0963(4) -0.2560(3) 0.6647(4) 0.0341(8) Uani 1 1 d . . . . .
H4F1 H -0.149741 -0.338936 0.62825 0.041 Uiso 1 1 calc R U . . .
C5F2 C 0.6319(4) 0.0957(4) 0.9640(4) 0.0376(9) Uani 1 1 d . . . . .
H5F2 H 0.695641 0.054066 0.927784 0.045 Uiso 1 1 calc R U . . .
C62 C -0.0226(4) 0.2829(3) 0.9144(3) 0.0255(7) Uani 1 1 d . . . . .
C6F2 C 0.4881(4) 0.0868(3) 0.8851(4) 0.0316(8) Uani 1 1 d . . . . .
H6F2 H 0.453721 0.037511 0.793505 0.038 Uiso 1 1 calc R U . . .
C32 C -0.0238(5) 0.5364(4) 1.2730(4) 0.0400(9) Uani 1 1 d . . . . .
H32A H -0.048229 0.608693 1.268412 0.06 Uiso 1 1 calc R U . . .
H32B H 0.075611 0.561886 1.344926 0.06 Uiso 1 1 calc R U . . .
H32C H -0.100868 0.49778 1.287607 0.06 Uiso 1 1 calc R U . . .
C22 C -0.1483(4) 0.4108(3) 1.0398(4) 0.0309(8) Uani 1 1 d . . . . .
H512 H 0.368(4) 0.322(3) 1.197(4) 0.021(9) Uiso 1 1 d . . . . .
H511 H 0.131(4) -0.120(4) 0.517(4) 0.036(11) Uiso 1 1 d . . . . .
H61 H 0.297(5) 0.375(4) 0.854(4) 0.041(12) Uiso 1 1 d . . . . .
H62 H -0.084(5) 0.189(4) 0.733(5) 0.050(14) Uiso 1 1 d . . . . .
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 0 '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 0.006 '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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -3 1 0.07
0 5 -1 0.103
11 -1 -7 0.21
-10 1 7 0.17
-1 12 9 0.052
0 -3 -2 0.079
-1 -4 -9 0.071
0 1 2 0.074
0 0 -1 0.05
-1 1 18 0.076
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
N52 NI N61 99.00(12) . .
N52 NI N51 170.60(11) . .
N61 NI N51 79.78(11) . .
N52 NI N62 79.26(12) . .
N61 NI N62 94.85(12) . .
N51 NI N62 110.10(12) . .
N52 NI N1F1 103.54(11) . .
N61 NI N1F1 157.46(12) . .
N51 NI N1F1 78.02(11) . .
N62 NI N1F1 89.15(11) . .
N52 NI N1F2 78.40(11) . .
N61 NI N1F2 91.32(11) . .
N51 NI N1F2 92.28(11) . .
N62 NI N1F2 157.50(12) . .
N1F1 NI N1F2 93.39(11) . .
C21 N11 C61 123.7(3) . .
C21 N11 C11 117.0(3) . .
C61 N11 C11 119.0(3) . .
C21 N31 C41 124.2(3) . .
C21 N31 C31 116.8(3) . .
C41 N31 C31 118.9(3) . .
C512 N52 C52 128.1(3) . .
C512 N52 NI 117.1(2) . .
C52 N52 NI 114.7(2) . .
C22 N12 C62 123.7(3) . .
C22 N12 C12 117.0(3) . .
C62 N12 C12 119.3(3) . .
C6F2 N1F2 C2F2 118.8(3) . .
C6F2 N1F2 NI 129.8(2) . .
C2F2 N1F2 NI 111.1(2) . .
C6F1 N1F1 C2F1 118.6(3) . .
C6F1 N1F1 NI 128.6(2) . .
C2F1 N1F1 NI 112.5(2) . .
C5F2 C4F2 C3F2 119.5(3) . .
C5F2 C4F2 H4F2 120.2 . .
C3F2 C4F2 H4F2 120.2 . .
C22 N32 C42 125.0(3) . .
C22 N32 C32 116.3(3) . .
C42 N32 C32 118.7(3) . .
C511 N51 C51 128.8(3) . .
C511 N51 NI 117.1(2) . .
C51 N51 NI 113.8(2) . .
C4F1 C5F1 C6F1 118.7(3) . .
C4F1 C5F1 H5F1 120.7 . .
C6F1 C5F1 H5F1 120.7 . .
C62 N62 NI 112.8(2) . .
C62 N62 H62 125(3) . .
NI N62 H62 122(3) . .
C61 N61 NI 113.0(2) . .
C61 N61 H61 117(3) . .
NI N61 H61 129(3) . .
O42 C42 C52 125.6(3) . .
O42 C42 N32 119.2(3) . .
C52 C42 N32 115.1(3) . .
N52 C52 C42 124.3(3) . .
N52 C52 C62 112.9(3) . .
C42 C52 C62 122.8(3) . .
C4F1 C3F1 C2F1 119.8(3) . .
C4F1 C3F1 H3F1 120.1 . .
C2F1 C3F1 H3F1 120.1 . .
C4F2 C3F2 C2F2 119.2(3) . .
C4F2 C3F2 H3F2 120.4 . .
C2F2 C3F2 H3F2 120.4 . .
N1F2 C2F2 C3F2 121.0(3) . .
N1F2 C2F2 C512 116.5(3) . .
C3F2 C2F2 C512 122.4(3) . .
N52 C512 C2F2 116.7(3) . .
N52 C512 H512 124(2) . .
C2F2 C512 H512 119(2) . .
N31 C31 H31A 109.5 . .
N31 C31 H31B 109.5 . .
H31A C31 H31B 109.5 . .
N31 C31 H31C 109.5 . .
H31A C31 H31C 109.5 . .
H31B C31 H31C 109.5 . .
N61 C61 N11 123.4(3) . .
N61 C61 C51 119.9(3) . .
N11 C61 C51 116.7(3) . .
N12 C12 H12A 109.5 . .
N12 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
N12 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
N51 C511 C2F1 116.2(3) . .
N51 C511 H511 124(2) . .
C2F1 C511 H511 120(2) . .
N11 C11 H11A 109.5 . .
N11 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
N11 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
N51 C51 C41 125.5(3) . .
N51 C51 C61 113.0(3) . .
C41 C51 C61 121.4(3) . .
O41 C41 C51 125.0(3) . .
O41 C41 N31 118.8(3) . .
C51 C41 N31 116.2(3) . .
N1F1 C6F1 C5F1 123.3(3) . .
N1F1 C6F1 H6F1 118.4 . .
C5F1 C6F1 H6F1 118.4 . .
N1F1 C2F1 C3F1 121.0(3) . .
N1F1 C2F1 C511 115.9(3) . .
C3F1 C2F1 C511 123.1(3) . .
O21 C21 N11 121.6(3) . .
O21 C21 N31 121.1(3) . .
N11 C21 N31 117.3(3) . .
C5F1 C4F1 C3F1 118.6(3) . .
C5F1 C4F1 H4F1 120.7 . .
C3F1 C4F1 H4F1 120.7 . .
C4F2 C5F2 C6F2 118.4(3) . .
C4F2 C5F2 H5F2 120.8 . .
C6F2 C5F2 H5F2 120.8 . .
N62 C62 N12 123.7(3) . .
N62 C62 C52 120.1(3) . .
N12 C62 C52 116.2(3) . .
N1F2 C6F2 C5F2 123.1(3) . .
N1F2 C6F2 H6F2 118.5 . .
C5F2 C6F2 H6F2 118.5 . .
N32 C32 H32A 109.5 . .
N32 C32 H32B 109.5 . .
H32A C32 H32B 109.5 . .
N32 C32 H32C 109.5 . .
H32A C32 H32C 109.5 . .
H32B C32 H32C 109.5 . .
O22 C22 N32 122.1(3) . .
O22 C22 N12 121.0(3) . .
N32 C22 N12 116.9(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
NI N52 2.027(3) .
NI N61 2.035(3) .
NI N51 2.037(3) .
NI N62 2.057(3) .
NI N1F1 2.103(3) .
NI N1F2 2.130(3) .
O42 C42 1.228(4) .
O41 C41 1.236(4) .
O22 C22 1.210(4) .
O21 C21 1.207(4) .
N11 C21 1.370(5) .
N11 C61 1.384(4) .
N11 C11 1.462(4) .
N31 C21 1.374(5) .
N31 C41 1.400(4) .
N31 C31 1.451(4) .
N52 C512 1.290(4) .
N52 C52 1.367(4) .
N12 C22 1.379(4) .
N12 C62 1.393(4) .
N12 C12 1.458(4) .
N1F2 C6F2 1.318(4) .
N1F2 C2F2 1.354(4) .
N1F1 C6F1 1.313(5) .
N1F1 C2F1 1.352(4) .
C4F2 C5F2 1.370(6) .
C4F2 C3F2 1.373(5) .
C4F2 H4F2 0.95 .
N32 C22 1.368(5) .
N32 C42 1.405(4) .
N32 C32 1.465(4) .
N51 C511 1.287(4) .
N51 C51 1.357(4) .
C5F1 C4F1 1.373(5) .
C5F1 C6F1 1.381(5) .
C5F1 H5F1 0.95 .
N62 C62 1.291(5) .
N62 H62 0.82(5) .
N61 C61 1.285(4) .
N61 H61 0.90(5) .
C42 C52 1.404(5) .
C52 C62 1.421(5) .
C3F1 C4F1 1.374(5) .
C3F1 C2F1 1.383(5) .
C3F1 H3F1 0.95 .
C3F2 C2F2 1.384(5) .
C3F2 H3F2 0.95 .
C2F2 C512 1.443(5) .
C512 H512 0.95(4) .
C31 H31A 0.98 .
C31 H31B 0.98 .
C31 H31C 0.98 .
C61 C51 1.437(5) .
C12 H12A 0.98 .
C12 H12B 0.98 .
C12 H12C 0.98 .
C511 C2F1 1.446(5) .
C511 H511 0.95(4) .
C11 H11A 0.98 .
C11 H11B 0.98 .
C11 H11C 0.98 .
C51 C41 1.400(5) .
C6F1 H6F1 0.95 .
C4F1 H4F1 0.95 .
C5F2 C6F2 1.378(5) .
C5F2 H5F2 0.95 .
C6F2 H6F2 0.95 .
C32 H32A 0.98 .
C32 H32B 0.98 .
C32 H32C 0.98 .
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
C22 N32 C42 O42 -178.3(3) . . . .
C32 N32 C42 O42 -1.5(5) . . . .
C22 N32 C42 C52 2.3(5) . . . .
C32 N32 C42 C52 179.0(3) . . . .
C512 N52 C52 C42 5.1(6) . . . .
NI N52 C52 C42 -172.9(3) . . . .
C512 N52 C52 C62 -177.6(3) . . . .
NI N52 C52 C62 4.5(4) . . . .
O42 C42 C52 N52 0.7(6) . . . .
N32 C42 C52 N52 -179.9(3) . . . .
O42 C42 C52 C62 -176.4(3) . . . .
N32 C42 C52 C62 3.0(5) . . . .
C5F2 C4F2 C3F2 C2F2 -0.1(6) . . . .
C6F2 N1F2 C2F2 C3F2 1.0(5) . . . .
NI N1F2 C2F2 C3F2 -173.2(3) . . . .
C6F2 N1F2 C2F2 C512 178.8(3) . . . .
NI N1F2 C2F2 C512 4.6(4) . . . .
C4F2 C3F2 C2F2 N1F2 -0.5(5) . . . .
C4F2 C3F2 C2F2 C512 -178.1(3) . . . .
C52 N52 C512 C2F2 -176.7(3) . . . .
NI N52 C512 C2F2 1.2(4) . . . .
N1F2 C2F2 C512 N52 -4.0(5) . . . .
C3F2 C2F2 C512 N52 173.7(3) . . . .
NI N61 C61 N11 -177.1(2) . . . .
NI N61 C61 C51 2.1(4) . . . .
C21 N11 C61 N61 178.5(3) . . . .
C11 N11 C61 N61 4.9(5) . . . .
C21 N11 C61 C51 -0.8(5) . . . .
C11 N11 C61 C51 -174.4(3) . . . .
C51 N51 C511 C2F1 178.8(3) . . . .
NI N51 C511 C2F1 6.0(4) . . . .
C511 N51 C51 C41 -3.7(6) . . . .
NI N51 C51 C41 169.3(3) . . . .
C511 N51 C51 C61 179.8(3) . . . .
NI N51 C51 C61 -7.2(3) . . . .
N61 C61 C51 N51 3.4(4) . . . .
N11 C61 C51 N51 -177.3(3) . . . .
N61 C61 C51 C41 -173.2(3) . . . .
N11 C61 C51 C41 6.1(5) . . . .
N51 C51 C41 O41 -3.1(5) . . . .
C61 C51 C41 O41 173.2(3) . . . .
N51 C51 C41 N31 177.3(3) . . . .
C61 C51 C41 N31 -6.5(5) . . . .
C21 N31 C41 O41 -177.9(3) . . . .
C31 N31 C41 O41 1.7(5) . . . .
C21 N31 C41 C51 1.8(5) . . . .
C31 N31 C41 C51 -178.7(3) . . . .
C2F1 N1F1 C6F1 C5F1 2.3(5) . . . .
NI N1F1 C6F1 C5F1 175.6(3) . . . .
C4F1 C5F1 C6F1 N1F1 -0.2(5) . . . .
C6F1 N1F1 C2F1 C3F1 -2.7(5) . . . .
NI N1F1 C2F1 C3F1 -177.1(3) . . . .
C6F1 N1F1 C2F1 C511 176.9(3) . . . .
NI N1F1 C2F1 C511 2.5(4) . . . .
C4F1 C3F1 C2F1 N1F1 1.1(5) . . . .
C4F1 C3F1 C2F1 C511 -178.5(3) . . . .
N51 C511 C2F1 N1F1 -5.6(5) . . . .
N51 C511 C2F1 C3F1 173.9(3) . . . .
C61 N11 C21 O21 177.1(3) . . . .
C11 N11 C21 O21 -9.2(5) . . . .
C61 N11 C21 N31 -3.6(5) . . . .
C11 N11 C21 N31 170.0(3) . . . .
C41 N31 C21 O21 -177.5(3) . . . .
C31 N31 C21 O21 2.9(5) . . . .
C41 N31 C21 N11 3.2(5) . . . .
C31 N31 C21 N11 -176.4(3) . . . .
C6F1 C5F1 C4F1 C3F1 -1.4(5) . . . .
C2F1 C3F1 C4F1 C5F1 1.0(5) . . . .
C3F2 C4F2 C5F2 C6F2 0.1(6) . . . .
NI N62 C62 N12 -179.2(3) . . . .
NI N62 C62 C52 -0.1(4) . . . .
C22 N12 C62 N62 -176.0(3) . . . .
C12 N12 C62 N62 2.0(5) . . . .
C22 N12 C62 C52 4.9(5) . . . .
C12 N12 C62 C52 -177.1(3) . . . .
N52 C52 C62 N62 -2.9(5) . . . .
C42 C52 C62 N62 174.5(3) . . . .
N52 C52 C62 N12 176.2(3) . . . .
C42 C52 C62 N12 -6.4(5) . . . .
C2F2 N1F2 C6F2 C5F2 -1.0(5) . . . .
NI N1F2 C6F2 C5F2 171.9(3) . . . .
C4F2 C5F2 C6F2 N1F2 0.5(6) . . . .
C42 N32 C22 O22 176.7(3) . . . .
C32 N32 C22 O22 -0.1(5) . . . .
C42 N32 C22 N12 -3.7(5) . . . .
C32 N32 C22 N12 179.5(3) . . . .
C62 N12 C22 O22 179.5(3) . . . .
C12 N12 C22 O22 1.4(5) . . . .
C62 N12 C22 N32 -0.2(5) . . . .
C12 N12 C22 N32 -178.2(3) . . . .
