#------------------------------------------------------------------------------
#$Date: 2019-10-03 11:39:50 +0300 (Thu, 03 Oct 2019) $
#$Revision: 219061 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/43/7234327.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_7234327
loop_
_publ_author_name
'Takuya Konno'
'Hiroki Kudo'
'Takayuki Ishida'
_publ_section_title
;
 Intermediate-paramagnetic phases with a half and a quarter spin entities
 in fluorinated biphenyl-3,5-diyl bis(tert-butyl nitroxides)
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              7813
_journal_page_last               7818
_journal_paper_doi               10.1039/C5TC00668F
_journal_volume                  3
_journal_year                    2015
_chemical_formula_moiety         'C20 H24 F2 N2 O2'
_chemical_formula_sum            'C20 H24 F2 N2 O2'
_chemical_formula_weight         362.42
_chemical_melting_point          365
_chemical_name_systematic
'2?,5?-difluorobiphenyl-3,5-diyl bis(tert-butyl nitroxide)'
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                111.13(4)
_cell_angle_beta                 93.65(3)
_cell_angle_gamma                116.77(3)
_cell_formula_units_Z            2
_cell_length_a                   9.549(4)
_cell_length_b                   10.244(5)
_cell_length_c                   12.036(5)
_cell_measurement_reflns_used    9533
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      1.89
_cell_volume                     943.7(9)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'CRYSTALS (Carruthers, et al., 1999)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12390
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             384.00
_exptl_crystal_preparation       'Magnetic properties'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane-hexane'
_exptl_crystal_size_max          0.409
_exptl_crystal_size_mid          0.371
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.774
_refine_diff_density_min         -0.497
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     304
_refine_ls_number_reflns         4292
_refine_ls_R_factor_gt           0.0689
_refine_ls_shift/su_max          0.009
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[0.0010Fo² + 2.5000σ(Fo²)]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0822
_reflns_number_gt                2104
_reflns_number_total             4292
_reflns_threshold_expression     F>2.0σ(F)
_cod_data_source_file            J-Mater-Chem-C-2015-3-7813.cif
_cod_data_source_block           25FBPBN_high_temperature_phase_296K
_cod_original_cell_volume        943.7(8)
_cod_database_code               7234327
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.3499(2) 0.5726(3) 0.03609(15) 0.0748(6) Uani 1.0 2 d . . .
F2 F 0.6952(3) 0.9906(3) 0.51307(18) 0.0914(7) Uani 1.0 2 d . . .
O1 O -0.2353(3) 0.3052(3) 0.39082(19) 0.0646(8) Uani 1.0 2 d . . .
O2 O -0.1484(2) -0.0485(2) 0.02493(16) 0.0466(6) Uani 1.0 2 d . . .
N1 N -0.1555(3) 0.4253(3) 0.36506(19) 0.0426(7) Uani 1.0 2 d . . .
N2 N -0.0896(3) 0.0750(3) -0.0013(2) 0.0406(7) Uani 1.0 2 d . . .
C1 C -0.0549(4) 0.4059(4) 0.2835(3) 0.0398(8) Uani 1.0 2 d . . .
C2 C -0.1150(4) 0.2539(4) 0.1855(3) 0.0407(9) Uani 1.0 2 d . . .
C3 C -0.0227(3) 0.2327(3) 0.1042(3) 0.0385(8) Uani 1.0 2 d . . .
C4 C 0.1319(4) 0.3595(4) 0.1216(3) 0.0404(9) Uani 1.0 2 d . . .
C5 C 0.1940(3) 0.5106(3) 0.2224(3) 0.0391(8) Uani 1.0 2 d . . .
C6 C 0.0985(4) 0.5327(4) 0.3021(3) 0.0401(8) Uani 1.0 2 d . . .
C7 C 0.3619(3) 0.6473(3) 0.2487(3) 0.0402(8) Uani 1.0 2 d . . .
C8 C 0.4351(4) 0.6734(4) 0.1574(3) 0.0489(9) Uani 1.0 2 d . . .
C9 C 0.5898(4) 0.8011(4) 0.1808(4) 0.0585(12) Uani 1.0 2 d . . .
C10 C 0.6783(5) 0.9090(5) 0.3017(4) 0.0628(12) Uani 1.0 2 d . . .
C11 C 0.6082(4) 0.8851(4) 0.3922(3) 0.0588(10) Uani 1.0 2 d . . .
C12 C 0.4550(4) 0.7585(4) 0.3700(3) 0.0483(10) Uani 1.0 2 d . . .
C13 C -0.2193(4) 0.5391(4) 0.3773(3) 0.0436(9) Uani 1.0 2 d . . .
C14 C -0.0820(5) 0.7121(5) 0.4393(5) 0.1191(18) Uani 1.0 2 d . . .
C15 C -0.3325(6) 0.5174(6) 0.4572(4) 0.116(2) Uani 1.0 2 d . . .
C16 C -0.3035(7) 0.4981(7) 0.2514(4) 0.134(3) Uani 1.0 2 d . . .
C17 C -0.1751(4) 0.0484(4) -0.1255(3) 0.0500(9) Uani 1.0 2 d . . .
C18 C -0.0745(7) 0.1929(6) -0.1496(5) 0.0928(17) Uani 1.0 2 d . . .
C19 C -0.3429(6) 0.0278(8) -0.1166(5) 0.0880(17) Uani 1.0 2 d . . .
C20 C -0.1931(6) -0.1035(6) -0.2241(4) 0.0697(14) Uani 1.0 2 d . . .
H1 H -0.220(4) 0.171(3) 0.171(3) 0.042(8) Uiso 1.0 2 d . . .
H2 H 0.203(3) 0.336(3) 0.065(3) 0.042(7) Uiso 1.0 2 d . . .
H3 H 0.143(3) 0.636(3) 0.373(3) 0.044(8) Uiso 1.0 2 d . . .
H4 H 0.620(4) 0.805(4) 0.115(3) 0.046(9) Uiso 1.0 2 d . . .
H5 H 0.778(4) 0.998(4) 0.324(3) 0.075(11) Uiso 1.0 2 d . . .
H6 H 0.413(3) 0.749(3) 0.434(3) 0.040(8) Uiso 1.0 2 d . . .
H7 H -0.1243 0.7830 0.4463 0.1409 Uiso 1.0 2 calc R . .
H8 H -0.0294 0.7355 0.5204 0.1412 Uiso 1.0 2 calc R . .
H9 H -0.0044 0.7289 0.3914 0.1411 Uiso 1.0 2 calc R . .
H10 H -0.4199 0.4063 0.4212 0.1876 Uiso 1.0 2 calc R . .
H11 H -0.2742 0.5450 0.5378 0.1874 Uiso 1.0 2 calc R . .
H12 H -0.3764 0.5871 0.4647 0.1872 Uiso 1.0 2 calc R . .
H13 H -0.3471 0.5676 0.2570 0.1850 Uiso 1.0 2 calc R . .
H14 H -0.2276 0.5130 0.2020 0.1852 Uiso 1.0 2 calc R . .
H15 H -0.3906 0.3869 0.2135 0.1852 Uiso 1.0 2 calc R . .
H16 H -0.131(4) 0.176(3) -0.232(4) 0.118(14) Uiso 1.0 2 d . . .
H17 H -0.071(5) 0.292(5) -0.089(4) 0.101(14) Uiso 1.0 2 d . . .
H18 H 0.041(6) 0.208(6) -0.156(5) 0.15(3) Uiso 1.0 2 d . . .
H19 H -0.396(6) -0.061(6) -0.099(4) 0.13(2) Uiso 1.0 2 d . . .
H20 H -0.320(5) 0.132(5) -0.052(4) 0.112(15) Uiso 1.0 2 d . . .
H21 H -0.402(4) 0.003(4) -0.203(4) 0.088(12) Uiso 1.0 2 d . . .
H22 H -0.261(5) -0.197(5) -0.217(4) 0.105(17) Uiso 1.0 2 d . . .
H23 H -0.085(4) -0.084(4) -0.235(3) 0.070(11) Uiso 1.0 2 d . . .
H24 H -0.250(4) -0.124(4) -0.305(3) 0.073(10) Uiso 1.0 2 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.006 0.003
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.017 0.010
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
O1 N1 C1 115.8(3) yes . . .
O1 N1 C13 117.9(3) yes . . .
C1 N1 C13 121.8(3) yes . . .
O2 N2 C3 115.1(3) yes . . .
O2 N2 C17 116.71(18) yes . . .
C3 N2 C17 118.7(3) yes . . .
N1 C1 C2 118.0(3) yes . . .
N1 C1 C6 121.8(3) yes . . .
C2 C1 C6 120.3(3) yes . . .
C1 C2 C3 119.2(3) yes . . .
N2 C3 C2 118.9(3) yes . . .
N2 C3 C4 120.0(3) yes . . .
C2 C3 C4 121.1(3) yes . . .
C3 C4 C5 119.4(3) yes . . .
C4 C5 C6 119.2(3) yes . . .
C4 C5 C7 121.4(3) yes . . .
C6 C5 C7 119.3(3) yes . . .
C1 C6 C5 120.7(3) yes . . .
C5 C7 C8 123.5(3) yes . . .
C5 C7 C12 120.8(3) yes . . .
C8 C7 C12 115.7(3) yes . . .
F1 C8 C7 119.2(3) yes . . .
F1 C8 C9 116.8(4) yes . . .
C7 C8 C9 123.9(3) yes . . .
C8 C9 C10 118.9(4) yes . . .
C9 C10 C11 117.9(3) yes . . .
F2 C11 C10 118.7(3) yes . . .
F2 C11 C12 117.7(4) yes . . .
C10 C11 C12 123.6(3) yes . . .
C7 C12 C11 119.9(4) yes . . .
N1 C13 C14 110.3(3) yes . . .
N1 C13 C15 108.2(4) yes . . .
N1 C13 C16 108.0(4) yes . . .
C14 C13 C15 107.8(3) yes . . .
C14 C13 C16 111.0(4) yes . . .
C15 C13 C16 111.6(4) yes . . .
N2 C17 C18 109.2(3) yes . . .
N2 C17 C19 106.9(4) yes . . .
N2 C17 C20 108.1(4) yes . . .
C18 C17 C19 111.3(5) yes . . .
C18 C17 C20 110.6(4) yes . . .
C19 C17 C20 110.6(3) yes . . .
C1 C2 H1 119.8(18) no . . .
C3 C2 H1 120.8(17) no . . .
C3 C4 H2 119.1(11) no . . .
C5 C4 H2 121.1(10) no . . .
C1 C6 H3 120.4(16) no . . .
C5 C6 H3 118.8(16) no . . .
C8 C9 H4 115(3) no . . .
C10 C9 H4 127(3) no . . .
C9 C10 H5 124(2) no . . .
C11 C10 H5 118(2) no . . .
C7 C12 H6 119.9(12) no . . .
C11 C12 H6 120.2(12) no . . .
C13 C14 H7 109.337 no . . .
C13 C14 H8 109.352 no . . .
C13 C14 H9 109.812 no . . .
H7 C14 H8 109.438 no . . .
H7 C14 H9 109.442 no . . .
H8 C14 H9 109.446 no . . .
C13 C15 H10 109.664 no . . .
C13 C15 H11 109.372 no . . .
C13 C15 H12 109.469 no . . .
H10 C15 H11 109.441 no . . .
H10 C15 H12 109.443 no . . .
H11 C15 H12 109.438 no . . .
C13 C16 H13 109.459 no . . .
C13 C16 H14 109.645 no . . .
C13 C16 H15 109.398 no . . .
H13 C16 H14 109.442 no . . .
H13 C16 H15 109.442 no . . .
H14 C16 H15 109.443 no . . .
C17 C18 H16 109.5(15) no . . .
C17 C18 H17 111(3) no . . .
C17 C18 H18 112(4) no . . .
H16 C18 H17 103(4) no . . .
H16 C18 H18 107(4) no . . .
H17 C18 H18 114(4) no . . .
C17 C19 H19 106(4) no . . .
C17 C19 H20 105(3) no . . .
C17 C19 H21 106(3) no . . .
H19 C19 H20 115(4) no . . .
H19 C19 H21 111(4) no . . .
H20 C19 H21 113(4) no . . .
C17 C20 H22 114(3) no . . .
C17 C20 H23 109.5(17) no . . .
C17 C20 H24 109(3) no . . .
H22 C20 H23 118(5) no . . .
H22 C20 H24 102(4) no . . .
H23 C20 H24 102(3) no . . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
F1 C8 1.366(4) yes . .
F2 C11 1.371(4) yes . .
O1 N1 1.285(4) yes . .
O2 N2 1.298(4) yes . .
N1 C1 1.442(4) yes . .
N1 C13 1.509(5) yes . .
N2 C3 1.455(3) yes . .
N2 C17 1.525(5) yes . .
C1 C2 1.389(4) yes . .
C1 C6 1.385(4) yes . .
C2 C3 1.383(5) yes . .
C3 C4 1.396(4) yes . .
C4 C5 1.396(4) yes . .
C5 C6 1.395(5) yes . .
C5 C7 1.492(4) yes . .
C7 C8 1.381(5) yes . .
C7 C12 1.394(4) yes . .
C8 C9 1.383(4) yes . .
C9 C10 1.378(5) yes . .
C10 C11 1.353(6) yes . .
C11 C12 1.373(4) yes . .
C13 C14 1.499(4) yes . .
C13 C15 1.488(7) yes . .
C13 C16 1.483(6) yes . .
C17 C18 1.504(7) yes . .
C17 C19 1.536(7) yes . .
C17 C20 1.504(6) yes . .
C2 H1 0.93(3) no . .
C4 H2 1.04(3) no . .
C6 H3 0.96(3) no . .
C9 H4 0.87(3) no . .
C10 H5 0.90(3) no . .
C12 H6 0.91(3) no . .
C14 H7 0.960 no . .
C14 H8 0.960 no . .
C14 H9 0.960 no . .
C15 H10 0.960 no . .
C15 H11 0.960 no . .
C15 H12 0.960 no . .
C16 H13 0.960 no . .
C16 H14 0.960 no . .
C16 H15 0.960 no . .
C18 H16 1.02(5) no . .
C18 H17 1.00(5) no . .
C18 H18 1.05(6) no . .
C19 H19 0.94(6) no . .
C19 H20 0.98(5) no . .
C19 H21 1.04(5) no . .
C20 H22 0.92(5) no . .
C20 H23 0.98(4) no . .
C20 H24 0.98(4) no . .
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
F1 C4 2.821(4) no . .
F1 C5 2.872(4) no . .
F2 C9 3.593(5) no . .
O1 C2 2.769(5) no . .
O1 C6 3.502(4) no . .
O1 C14 3.536(6) no . .
O1 C15 2.624(7) no . .
O1 C16 3.249(8) no . .
O2 C2 2.854(4) no . .
O2 C4 3.465(4) no . .
O2 C19 2.971(8) no . .
O2 C20 2.809(5) no . .
C1 C4 2.783(5) no . .
C1 C14 3.158(6) no . .
C1 C16 2.973(9) no . .
C2 C5 2.797(4) no . .
C2 C13 3.593(6) no . .
C2 C16 3.596(9) no . .
C2 C17 3.425(5) no . .
C2 C19 3.421(6) no . .
C3 C6 2.762(4) no . .
C3 C18 2.910(7) no . .
C3 C19 3.159(6) no . .
C4 C8 3.060(5) no . .
C4 C17 3.352(4) no . .
C4 C18 3.097(6) no . .
C6 C12 2.966(4) no . .
C6 C13 3.243(5) no . .
C6 C14 3.178(7) no . .
C7 C10 2.819(5) no . .
C8 C11 2.679(5) no . .
C9 C12 2.760(6) no . .
F1 C16 3.225(5) no . 2_565
F2 C12 3.408(5) no . 2_676
F2 C14 3.404(5) no . 2_676
O1 C6 3.336(4) no . 2_566
O1 C10 3.470(6) no . 1_445
O2 O2 2.736(3) no . 2_555
O2 N2 2.429(4) no . 2_555
O2 C3 3.104(5) no . 2_555
O2 C4 3.119(5) no . 2_555
O2 C9 3.370(5) no . 1_445
O2 C17 3.244(5) no . 2_555
O2 C20 3.248(6) no . 2_555
N1 N1 3.579(4) no . 2_566
N2 O2 2.429(4) no . 2_555
N2 N2 2.773(5) no . 2_555
N2 C20 3.539(7) no . 2_555
C3 O2 3.104(5) no . 2_555
C3 C20 3.397(8) no . 2_555
C4 O2 3.119(5) no . 2_555
C4 C20 3.517(8) no . 2_555
C6 O1 3.336(4) no . 2_566
C9 O2 3.370(5) no . 1_665
C10 O1 3.470(6) no . 1_665
C12 F2 3.408(5) no . 2_676
C14 F2 3.404(5) no . 2_676
C15 C15 3.328(8) no . 2_466
C16 F1 3.225(5) no . 2_565
C17 O2 3.244(5) no . 2_555
C20 O2 3.248(6) no . 2_555
C20 N2 3.539(7) no . 2_555
C20 C3 3.397(8) no . 2_555
C20 C4 3.517(8) no . 2_555
F1 H2 2.36(3) no . .
F1 H4 2.40(3) no . .
F1 H17 3.52(4) no . .
F1 H18 3.31(4) no . .
F2 H5 2.47(4) no . .
F2 H6 2.50(2) no . .
O1 H1 2.55(3) no . .
O1 H8 3.5468 no . .
O1 H10 2.4010 no . .
O1 H11 2.6592 no . .
O1 H12 3.5704 no . .
O1 H15 3.0745 no . .
O2 H1 2.70(4) no . .
O2 H19 2.64(6) no . .
O2 H20 3.28(6) no . .
O2 H22 2.63(4) no . .
O2 H23 3.15(4) no . .
N1 H1 2.57(3) no . .
N1 H3 2.66(3) no . .
N1 H7 3.2959 no . .
N1 H8 2.6510 no . .
N1 H9 2.6536 no . .
N1 H10 2.5950 no . .
N1 H11 2.6117 no . .
N1 H12 3.2658 no . .
N1 H13 3.2601 no . .
N1 H14 2.6050 no . .
N1 H15 2.5854 no . .
N2 H1 2.60(3) no . .
N2 H2 2.66(2) no . .
N2 H16 3.35(5) no . .
N2 H17 2.73(6) no . .
N2 H18 2.73(6) no . .
N2 H19 2.57(5) no . .
N2 H20 2.61(6) no . .
N2 H21 3.34(5) no . .
N2 H22 2.71(4) no . .
N2 H23 2.71(4) no . .
N2 H24 3.31(4) no . .
C1 H8 3.4386 no . .
C1 H9 2.8730 no . .
C1 H14 2.6617 no . .
C1 H15 3.1619 no . .
C2 H2 3.34(3) no . .
C2 H3 3.28(2) no . .
C2 H14 3.2343 no . .
C2 H15 3.4504 no . .
C2 H17 3.50(5) no . .
C2 H19 3.52(4) no . .
C2 H20 2.84(5) no . .
C3 H17 2.67(5) no . .
C3 H18 3.17(6) no . .
C3 H19 3.42(4) no . .
C3 H20 2.82(5) no . .
C4 H1 3.26(3) no . .
C4 H3 3.27(3) no . .
C4 H17 2.75(5) no . .
C4 H18 3.00(5) no . .
C5 H6 2.66(2) no . .
C6 H1 3.24(2) no . .
C6 H2 3.35(3) no . .
C6 H6 2.70(2) no . .
C6 H8 3.3864 no . .
C6 H9 2.5525 no . .
C6 H14 3.1573 no . .
C7 H2 2.74(2) no . .
C7 H3 2.63(3) no . .
C7 H4 3.18(3) no . .
C8 H2 2.85(3) no . .
C8 H5 3.22(3) no . .
C8 H6 3.18(3) no . .
C10 H6 3.21(3) no . .
C11 H4 3.16(3) no . .
C12 H3 2.67(3) no . .
C12 H5 3.19(4) no . .
C13 H3 3.15(3) no . .
C14 H3 2.67(4) no . .
C14 H10 3.2532 no . .
C14 H11 2.5716 no . .
C14 H12 2.6042 no . .
C14 H13 2.6442 no . .
C14 H14 2.6440 no . .
C14 H15 3.2835 no . .
C15 H7 2.6061 no . .
C15 H8 2.5725 no . .
C15 H9 3.2521 no . .
C15 H13 2.6476 no . .
C15 H14 3.2824 no . .
C15 H15 2.6453 no . .
C16 H7 2.6468 no . .
C16 H8 3.2801 no . .
C16 H9 2.6494 no . .
C16 H10 2.6511 no . .
C16 H11 3.2794 no . .
C16 H12 2.6488 no . .
C17 H1 3.46(3) no . .
C17 H2 3.388(19) no . .
C18 H2 2.96(3) no . .
C18 H19 3.28(5) no . .
C18 H20 2.61(5) no . .
C18 H21 2.71(4) no . .
C18 H22 3.29(5) no . .
C18 H23 2.60(4) no . .
C18 H24 2.67(3) no . .
C19 H1 3.13(3) no . .
C19 H16 2.73(5) no . .
C19 H17 2.67(4) no . .
C19 H18 3.44(6) no . .
C19 H22 2.67(6) no . .
C19 H23 3.35(5) no . .
C19 H24 2.70(4) no . .
C20 H16 2.69(4) no . .
C20 H17 3.35(5) no . .
C20 H18 2.70(5) no . .
C20 H19 2.63(6) no . .
C20 H20 3.31(5) no . .
C20 H21 2.66(5) no . .
H1 H14 3.4256 no . .
H1 H15 3.2191 no . .
H1 H19 3.03(5) no . .
H1 H20 2.62(6) no . .
H2 H17 2.87(6) no . .
H2 H18 2.52(6) no . .
H3 H6 2.23(4) no . .
H3 H7 3.5143 no . .
H3 H8 2.7349 no . .
H3 H9 2.0077 no . .
H3 H14 3.3971 no . .
H4 H5 2.40(4) no . .
H7 H10 3.4908 no . .
H7 H11 2.8631 no . .
H7 H12 2.4299 no . .
H7 H13 2.4733 no . .
H7 H14 2.9288 no . .
H7 H15 3.5194 no . .
H8 H10 3.4503 no . .
H8 H11 2.3590 no . .
H8 H12 2.8601 no . .
H8 H13 3.5149 no . .
H8 H14 3.5149 no . .
H9 H11 3.4478 no . .
H9 H12 3.4891 no . .
H9 H13 2.9297 no . .
H9 H14 2.4760 no . .
H9 H15 3.5226 no . .
H10 H13 2.9348 no . .
H10 H14 3.5227 no . .
H10 H15 2.4787 no . .
H11 H13 3.5173 no . .
H11 H15 3.5156 no . .
H12 H13 2.4787 no . .
H12 H14 3.5210 no . .
H12 H15 2.9306 no . .
H16 H19 3.56(7) no . .
H16 H20 2.94(7) no . .
H16 H21 2.53(5) no . .
H16 H22 3.52(6) no . .
H16 H23 2.88(6) no . .
H16 H24 2.50(4) no . .
H17 H19 3.51(6) no . .
H17 H20 2.39(6) no . .
H17 H21 2.96(4) no . .
H17 H23 3.55(7) no . .
H17 H24 3.57(5) no . .
H18 H20 3.59(7) no . .
H18 H22 3.58(7) no . .
H18 H23 2.42(6) no . .
H18 H24 2.99(5) no . .
H19 H22 2.46(8) no . .
H19 H23 3.54(7) no . .
H19 H24 2.94(7) no . .
H20 H22 3.56(8) no . .
H20 H24 3.56(6) no . .
H21 H22 2.89(8) no . .
H21 H23 3.53(7) no . .
H21 H24 2.47(6) no . .
F1 H13 3.2878 no . 2_565
F1 H14 2.6809 no . 2_565
F1 H15 3.2020 no . 2_565
F1 H17 3.51(6) no . 2_565
F1 H20 3.10(6) no . 2_565
F2 H3 3.08(3) no . 2_676
F2 H6 3.15(4) no . 2_676
F2 H7 3.2229 no . 1_655
F2 H7 3.5739 no . 2_676
F2 H8 3.3362 no . 2_676
F2 H9 2.8002 no . 2_676
F2 H16 2.84(4) no . 1_666
F2 H21 3.57(5) no . 1_666
F2 H24 2.95(5) no . 1_666
O1 H3 2.68(3) no . 2_566
O1 H5 3.01(5) no . 1_445
O1 H6 2.84(3) no . 2_566
O1 H8 2.9387 no . 2_566
O1 H9 3.5846 no . 2_566
O1 H21 3.33(3) no . 2_455
O2 H2 2.52(3) no . 2_555
O2 H4 2.61(3) no . 1_445
O2 H18 3.06(7) no . 2_555
O2 H22 3.57(4) no . 2_555
O2 H23 2.70(4) no . 2_555
N1 H3 3.44(4) no . 2_566
N1 H8 3.4185 no . 2_566
N2 H2 3.60(3) no . 2_555
N2 H22 3.53(5) no . 2_555
N2 H23 3.16(4) no . 2_555
C1 H8 3.4050 no . 2_566
C1 H11 3.4190 no . 2_566
C2 H5 3.41(4) no . 1_445
C2 H23 3.26(5) no . 2_555
C3 H22 3.18(6) no . 2_555
C3 H23 2.97(5) no . 2_555
C4 H22 2.95(6) no . 2_555
C4 H23 3.43(5) no . 2_555
C5 H11 3.2463 no . 2_566
C5 H16 3.49(4) no . 2_565
C5 H17 3.50(6) no . 2_565
C5 H22 3.53(6) no . 2_555
C6 H11 3.0093 no . 2_566
C6 H16 3.27(4) no . 2_565
C7 H13 3.2349 no . 1_655
C7 H16 3.46(4) no . 2_565
C8 H13 3.0959 no . 1_655
C8 H20 3.23(6) no . 2_565
C8 H21 3.32(5) no . 2_565
C9 H1 3.44(3) no . 1_665
C9 H13 3.1195 no . 1_655
C9 H18 3.60(7) no . 2_665
C9 H20 3.37(6) no . 2_565
C9 H21 3.19(5) no . 2_565
C10 H1 3.39(4) no . 1_665
C10 H7 3.4124 no . 1_655
C10 H8 3.3993 no . 2_676
C10 H13 3.2312 no . 1_655
C10 H21 3.41(5) no . 2_565
C11 H7 3.2753 no . 1_655
C11 H12 3.5224 no . 1_655
C11 H13 3.3056 no . 1_655
C12 H10 3.4549 no . 2_566
C12 H11 3.4313 no . 2_566
C12 H12 3.2760 no . 1_655
C12 H13 3.3142 no . 1_655
C14 H5 3.23(3) no . 2_676
C14 H16 3.51(5) no . 2_565
C15 H6 3.25(4) no . 2_566
C15 H10 3.1020 no . 2_466
C15 H11 3.5229 no . 2_466
C15 H12 2.8521 no . 2_466
C15 H24 3.44(4) no . 1_566
C16 H18 3.57(6) no . 2_565
C18 H9 3.3308 no . 2_565
C18 H14 3.4012 no . 2_565
C19 H15 3.4921 no . 2_455
C20 H2 3.53(4) no . 2_555
C20 H10 3.4868 no . 2_455
C20 H11 3.3982 no . 1_544
C20 H12 3.5706 no . 1_544
H1 C9 3.44(3) no . 1_445
H1 C10 3.39(4) no . 1_445
H1 H4 3.12(5) no . 1_445
H1 H5 2.97(6) no . 1_445
H1 H19 3.26(6) no . 2_455
H1 H21 3.35(5) no . 2_455
H1 H23 3.52(6) no . 2_555
H2 O2 2.52(3) no . 2_555
H2 N2 3.60(3) no . 2_555
H2 C20 3.53(4) no . 2_555
H2 H4 3.17(5) no . 2_665
H2 H22 2.86(7) no . 2_555
H3 F2 3.08(3) no . 2_676
H3 O1 2.68(3) no . 2_566
H3 N1 3.44(4) no . 2_566
H3 H11 3.0852 no . 2_566
H3 H16 3.02(6) no . 2_565
H4 O2 2.61(3) no . 1_665
H4 H1 3.12(5) no . 1_665
H4 H2 3.17(5) no . 2_665
H4 H13 3.5455 no . 1_655
H4 H18 3.31(8) no . 2_665
H4 H19 3.34(7) no . 1_665
H4 H20 3.31(7) no . 2_565
H4 H21 3.43(6) no . 2_565
H5 O1 3.01(5) no . 1_665
H5 C2 3.41(4) no . 1_665
H5 C14 3.23(3) no . 2_676
H5 H1 2.97(6) no . 1_665
H5 H7 3.4540 no . 1_655
H5 H7 3.3616 no . 2_676
H5 H8 2.5610 no . 2_676
H5 H9 3.3054 no . 2_676
H5 H18 3.50(8) no . 2_665
H5 H23 3.05(6) no . 2_665
H6 F2 3.15(4) no . 2_676
H6 O1 2.84(3) no . 2_566
H6 C15 3.25(4) no . 2_566
H6 H10 2.7659 no . 2_566
H6 H11 2.8524 no . 2_566
H6 H12 3.2096 no . 1_655
H7 F2 3.2229 no . 1_455
H7 F2 3.5739 no . 2_676
H7 C10 3.4124 no . 1_455
H7 C11 3.2753 no . 1_455
H7 H5 3.4540 no . 1_455
H7 H5 3.3616 no . 2_676
H7 H23 3.5071 no . 1_566
H7 H24 3.2763 no . 1_566
H8 F2 3.3362 no . 2_676
H8 O1 2.9387 no . 2_566
H8 N1 3.4185 no . 2_566
H8 C1 3.4050 no . 2_566
H8 C10 3.3993 no . 2_676
H8 H5 2.5610 no . 2_676
H8 H23 3.0876 no . 1_566
H8 H24 3.4690 no . 1_566
H9 F2 2.8002 no . 2_676
H9 O1 3.5846 no . 2_566
H9 C18 3.3308 no . 2_565
H9 H5 3.3054 no . 2_676
H9 H16 2.6139 no . 2_565
H9 H18 3.1557 no . 2_565
H10 C12 3.4549 no . 2_566
H10 C15 3.1020 no . 2_466
H10 C20 3.4868 no . 2_455
H10 H6 2.7659 no . 2_566
H10 H10 3.1646 no . 2_466
H10 H11 3.2166 no . 2_466
H10 H12 2.4637 no . 2_466
H10 H21 3.5293 no . 2_455
H10 H22 3.0466 no . 2_455
H10 H24 2.9303 no . 2_455
H11 C1 3.4190 no . 2_566
H11 C5 3.2463 no . 2_566
H11 C6 3.0093 no . 2_566
H11 C12 3.4313 no . 2_566
H11 C15 3.5229 no . 2_466
H11 C20 3.3982 no . 1_566
H11 H3 3.0852 no . 2_566
H11 H6 2.8524 no . 2_566
H11 H10 3.2166 no . 2_466
H11 H12 2.9763 no . 2_466
H11 H22 3.1196 no . 1_566
H11 H23 3.2984 no . 1_566
H11 H24 3.1242 no . 1_566
H12 C11 3.5224 no . 1_455
H12 C12 3.2760 no . 1_455
H12 C15 2.8521 no . 2_466
H12 C20 3.5706 no . 1_566
H12 H6 3.2096 no . 1_455
H12 H10 2.4637 no . 2_466
H12 H11 2.9763 no . 2_466
H12 H12 2.6530 no . 2_466
H12 H22 3.4534 no . 1_566
H12 H24 2.8905 no . 1_566
H13 F1 3.2878 no . 2_565
H13 C7 3.2349 no . 1_455
H13 C8 3.0959 no . 1_455
H13 C9 3.1195 no . 1_455
H13 C10 3.2312 no . 1_455
H13 C11 3.3056 no . 1_455
H13 C12 3.3142 no . 1_455
H13 H4 3.5455 no . 1_455
H13 H18 3.4231 no . 2_565
H14 F1 2.6809 no . 2_565
H14 C18 3.4012 no . 2_565
H14 H16 3.3464 no . 2_565
H14 H17 3.3562 no . 2_565
H14 H18 2.8853 no . 2_565
H15 F1 3.2020 no . 2_565
H15 C19 3.4921 no . 2_455
H15 H19 2.7171 no . 2_455
H15 H21 3.5209 no . 2_455
H15 H22 3.0191 no . 2_455
H16 F2 2.84(4) no . 1_444
H16 C5 3.49(4) no . 2_565
H16 C6 3.27(4) no . 2_565
H16 C7 3.46(4) no . 2_565
H16 C14 3.51(5) no . 2_565
H16 H3 3.02(6) no . 2_565
H16 H9 2.6139 no . 2_565
H16 H14 3.3464 no . 2_565
H17 F1 3.51(6) no . 2_565
H17 C5 3.50(6) no . 2_565
H17 H14 3.3562 no . 2_565
H17 H17 3.52(6) no . 2_565
H18 O2 3.06(7) no . 2_555
H18 C9 3.60(7) no . 2_665
H18 C16 3.57(6) no . 2_565
H18 H4 3.31(8) no . 2_665
H18 H5 3.50(8) no . 2_665
H18 H9 3.1557 no . 2_565
H18 H13 3.4231 no . 2_565
H18 H14 2.8853 no . 2_565
H19 H1 3.26(6) no . 2_455
H19 H4 3.34(7) no . 1_445
H19 H15 2.7171 no . 2_455
H19 H19 3.44(8) no . 2_455
H19 H20 3.31(7) no . 2_455
H20 F1 3.10(6) no . 2_565
H20 C8 3.23(6) no . 2_565
H20 C9 3.37(6) no . 2_565
H20 H4 3.31(7) no . 2_565
H20 H19 3.31(7) no . 2_455
H21 F2 3.57(5) no . 1_444
H21 O1 3.33(3) no . 2_455
H21 C8 3.32(5) no . 2_565
H21 C9 3.19(5) no . 2_565
H21 C10 3.41(5) no . 2_565
H21 H1 3.35(5) no . 2_455
H21 H4 3.43(6) no . 2_565
H21 H10 3.5293 no . 2_455
H21 H15 3.5209 no . 2_455
H22 O2 3.57(4) no . 2_555
H22 N2 3.53(5) no . 2_555
H22 C3 3.18(6) no . 2_555
H22 C4 2.95(6) no . 2_555
H22 C5 3.53(6) no . 2_555
H22 H2 2.86(7) no . 2_555
H22 H10 3.0466 no . 2_455
H22 H11 3.1196 no . 1_544
H22 H12 3.4534 no . 1_544
H22 H15 3.0191 no . 2_455
H23 O2 2.70(4) no . 2_555
H23 N2 3.16(4) no . 2_555
H23 C2 3.26(5) no . 2_555
H23 C3 2.97(5) no . 2_555
H23 C4 3.43(5) no . 2_555
H23 H1 3.52(6) no . 2_555
H23 H5 3.05(6) no . 2_665
H23 H7 3.5071 no . 1_544
H23 H8 3.0876 no . 1_544
H23 H11 3.2984 no . 1_544
H24 F2 2.95(5) no . 1_444
H24 C15 3.44(4) no . 1_544
H24 H7 3.2763 no . 1_544
H24 H8 3.4690 no . 1_544
H24 H10 2.9303 no . 2_455
H24 H11 3.1242 no . 1_544
H24 H12 2.8905 no . 1_544
N1 N1 3.579(4) no . 2_566
O1 O1 4.221(4) no . 2_566
O1 N1 3.696(4) no . 2_566
N1 O1 3.696(4) no . 2_566
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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O1 N1 C1 C2 38.8(4) no . . . .
O1 N1 C1 C6 -140.0(3) no . . . .
O1 N1 C13 C14 136.5(2) no . . . .
O1 N1 C13 C15 18.8(3) no . . . .
O1 N1 C13 C16 -102.1(3) no . . . .
C1 N1 C13 C14 -68.4(3) no . . . .
C1 N1 C13 C15 173.91(15) no . . . .
C1 N1 C13 C16 53.0(3) no . . . .
C13 N1 C1 C2 -116.8(3) no . . . .
C13 N1 C1 C6 64.4(4) no . . . .
O2 N2 C3 C2 -49.5(4) no . . . .
O2 N2 C3 C4 130.7(3) no . . . .
O2 N2 C17 C18 -170.2(3) no . . . .
O2 N2 C17 C19 69.3(3) no . . . .
O2 N2 C17 C20 -49.9(4) no . . . .
C3 N2 C17 C18 45.0(4) no . . . .
C3 N2 C17 C19 -75.5(3) no . . . .
C3 N2 C17 C20 165.4(2) no . . . .
C17 N2 C3 C2 95.8(4) no . . . .
C17 N2 C3 C4 -84.0(4) no . . . .
N1 C1 C2 C3 178.5(3) no . . . .
N1 C1 C6 C5 179.6(3) no . . . .
C2 C1 C6 C5 0.8(6) no . . . .
C6 C1 C2 C3 -2.6(6) no . . . .
C1 C2 C3 N2 -177.3(3) no . . . .
C1 C2 C3 C4 2.5(6) no . . . .
N2 C3 C4 C5 179.4(3) no . . . .
C2 C3 C4 C5 -0.4(6) no . . . .
C3 C4 C5 C6 -1.4(6) no . . . .
C3 C4 C5 C7 176.8(3) no . . . .
C4 C5 C6 C1 1.3(6) no . . . .
C4 C5 C7 C8 34.3(6) no . . . .
C4 C5 C7 C12 -146.0(4) no . . . .
C6 C5 C7 C8 -147.5(4) no . . . .
C6 C5 C7 C12 32.2(5) no . . . .
C7 C5 C6 C1 -177.0(3) no . . . .
C5 C7 C8 F1 1.7(6) no . . . .
C5 C7 C8 C9 179.1(4) no . . . .
C5 C7 C12 C11 -178.9(4) no . . . .
C8 C7 C12 C11 0.8(6) no . . . .
C12 C7 C8 F1 -178.0(4) no . . . .
C12 C7 C8 C9 -0.7(6) no . . . .
F1 C8 C9 C10 177.9(4) no . . . .
C7 C8 C9 C10 0.5(7) no . . . .
C8 C9 C10 C11 -0.5(7) no . . . .
C9 C10 C11 F2 179.4(4) no . . . .
C9 C10 C11 C12 0.7(8) no . . . .
F2 C11 C12 C7 -179.7(4) no . . . .
C10 C11 C12 C7 -0.9(7) no . . . .
