#------------------------------------------------------------------------------
#$Date: 2019-10-03 10:39:50 +0200 (jue 03 de oct de 2019) $
#$Revision: 219061 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/43/7234325.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_7234325
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 H25 F N2 O2'
_chemical_formula_sum            'C20 H25 F N2 O2'
_chemical_formula_weight         344.43
_chemical_melting_point          356
_chemical_name_systematic
'3?-fluorobiphenyl-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                109.5739(13)
_cell_angle_beta                 95.7112(13)
_cell_angle_gamma                116.1439(9)
_cell_formula_units_Z            2
_cell_length_a                   9.4585(4)
_cell_length_b                   10.1452(3)
_cell_length_c                   11.4899(5)
_cell_measurement_reflns_used    15100
_cell_measurement_temperature    163
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.42
_cell_volume                     891.86(6)
_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    'Superflip (Palatinus, et al., 2007)'
_diffrn_ambient_temperature      163
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0791
_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       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16636
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.48
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             368.00
_exptl_crystal_preparation       'Magnetic properties'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane-hexane'
_exptl_crystal_size_max          0.336
_exptl_crystal_size_mid          0.264
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.423
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4093
_refine_ls_R_factor_gt           0.0517
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[0.0005Fo² + 2.0000σ(Fo²)]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0515
_reflns_number_gt                3218
_reflns_number_total             4093
_reflns_threshold_expression     F>2.0σ(F)
_cod_data_source_file            J-Mater-Chem-C-2015-3-7813.cif
_cod_data_source_block           3FBPBN_163K
_cod_original_cell_volume        891.86(7)
_cod_database_code               7234325
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 0.69804(11) 0.99693(11) 0.50082(8) 0.0331(3) Uani 1.0 2 d . . .
O1 O -0.24463(12) 0.29517(11) 0.38553(9) 0.0199(3) Uani 1.0 2 d . . .
O2 O -0.14526(11) -0.05145(11) 0.02451(9) 0.0162(3) Uani 1.0 2 d . . .
N1 N -0.15929(13) 0.41868(13) 0.36257(10) 0.0146(3) Uani 1.0 2 d . . .
N2 N -0.09236(13) 0.06819(13) -0.00795(10) 0.0140(3) Uani 1.0 2 d . . .
C1 C -0.05802(16) 0.39983(16) 0.28052(12) 0.0145(4) Uani 1.0 2 d . . .
C2 C -0.11968(17) 0.24666(16) 0.18044(13) 0.0151(4) Uani 1.0 2 d . . .
C3 C -0.02758(16) 0.22631(15) 0.09682(12) 0.0140(4) Uani 1.0 2 d . . .
C4 C 0.12545(16) 0.35369(16) 0.11375(13) 0.0149(4) Uani 1.0 2 d . . .
C5 C 0.18881(16) 0.50570(16) 0.21580(13) 0.0141(4) Uani 1.0 2 d . . .
C6 C 0.09504(16) 0.52754(16) 0.29954(13) 0.0146(4) Uani 1.0 2 d . . .
C7 C 0.35598(16) 0.64034(15) 0.23780(13) 0.0150(4) Uani 1.0 2 d . . .
C8 C 0.42026(17) 0.65070(17) 0.13466(14) 0.0169(4) Uani 1.0 2 d . . .
C9 C 0.57547(18) 0.77561(17) 0.15473(14) 0.0200(4) Uani 1.0 2 d . . .
C10 C 0.67159(18) 0.89469(18) 0.27832(15) 0.0223(4) Uani 1.0 2 d . . .
C11 C 0.60590(17) 0.88282(16) 0.37855(14) 0.0210(4) Uani 1.0 2 d . . .
C12 C 0.45219(17) 0.75992(17) 0.36251(13) 0.0183(4) Uani 1.0 2 d . . .
C13 C -0.22095(16) 0.53470(16) 0.37082(13) 0.0162(4) Uani 1.0 2 d . . .
C14 C -0.08127(19) 0.71013(17) 0.44374(16) 0.0218(4) Uani 1.0 2 d . . .
C15 C -0.3494(2) 0.5028(2) 0.44309(17) 0.0235(5) Uani 1.0 2 d . . .
C16 C -0.2990(2) 0.4994(2) 0.23311(15) 0.0247(5) Uani 1.0 2 d . . .
C17 C -0.18390(17) 0.03461(16) -0.13960(13) 0.0174(4) Uani 1.0 2 d . . .
C18 C -0.0893(3) 0.1761(2) -0.17269(16) 0.0294(5) Uani 1.0 2 d . . .
C19 C -0.35387(19) 0.0113(2) -0.13383(16) 0.0272(5) Uani 1.0 2 d . . .
C20 C -0.2024(2) -0.11918(19) -0.23953(14) 0.0220(4) Uani 1.0 2 d . . .
H1 H -0.224(2) 0.1604(19) 0.1709(15) 0.019(4) Uiso 1.0 2 d . . .
H2 H 0.187(2) 0.3353(19) 0.0580(16) 0.025(5) Uiso 1.0 2 d . . .
H3 H 0.1376(18) 0.6253(18) 0.3677(14) 0.014(4) Uiso 1.0 2 d . . .
H4 H 0.3503(18) 0.5661(18) 0.0485(14) 0.015(4) Uiso 1.0 2 d . . .
H5 H 0.6188(19) 0.7831(19) 0.0815(15) 0.022(4) Uiso 1.0 2 d . . .
H6 H 0.776(3) 0.980(2) 0.2931(16) 0.031(5) Uiso 1.0 2 d . . .
H7 H 0.4151(19) 0.7575(18) 0.4397(16) 0.023(4) Uiso 1.0 2 d . . .
H8 H -0.006(2) 0.7449(19) 0.3979(16) 0.026(5) Uiso 1.0 2 d . . .
H9 H -0.134(3) 0.780(2) 0.4622(17) 0.036(5) Uiso 1.0 2 d . . .
H10 H -0.016(3) 0.726(3) 0.5241(19) 0.039(5) Uiso 1.0 2 d . . .
H11 H -0.442(2) 0.389(2) 0.3933(15) 0.022(4) Uiso 1.0 2 d . . .
H12 H -0.300(2) 0.526(2) 0.5308(17) 0.026(5) Uiso 1.0 2 d . . .
H13 H -0.3917(19) 0.5740(19) 0.4431(16) 0.027(5) Uiso 1.0 2 d . . .
H14 H -0.387(3) 0.388(3) 0.1872(16) 0.027(5) Uiso 1.0 2 d . . .
H15 H -0.349(2) 0.566(2) 0.2341(16) 0.033(5) Uiso 1.0 2 d . . .
H16 H -0.218(2) 0.516(2) 0.1817(17) 0.029(5) Uiso 1.0 2 d . . .
H17 H -0.148(3) 0.149(2) -0.2621(18) 0.032(5) Uiso 1.0 2 d . . .
H18 H -0.077(2) 0.277(2) -0.1113(16) 0.026(5) Uiso 1.0 2 d . . .
H19 H 0.023(3) 0.192(3) -0.1729(18) 0.049(6) Uiso 1.0 2 d . . .
H20 H -0.342(3) 0.115(3) -0.0686(18) 0.041(5) Uiso 1.0 2 d . . .
H21 H -0.416(2) -0.015(2) -0.2167(18) 0.030(5) Uiso 1.0 2 d . . .
H22 H -0.414(3) -0.081(3) -0.1057(17) 0.033(5) Uiso 1.0 2 d . . .
H23 H -0.095(2) -0.102(2) -0.2451(16) 0.030(5) Uiso 1.0 2 d . . .
H24 H -0.263(3) -0.215(3) -0.2225(16) 0.032(5) Uiso 1.0 2 d . . .
H25 H -0.263(2) -0.141(2) -0.3256(17) 0.028(5) 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 115.62(13) yes . . .
O1 N1 C13 118.34(12) yes . . .
C1 N1 C13 120.66(14) yes . . .
O2 N2 C3 115.26(12) yes . . .
O2 N2 C17 116.49(9) yes . . .
C3 N2 C17 118.62(14) yes . . .
N1 C1 C2 117.31(12) yes . . .
N1 C1 C6 121.75(12) yes . . .
C2 C1 C6 120.94(15) yes . . .
C1 C2 C3 118.61(12) yes . . .
N2 C3 C2 118.66(11) yes . . .
N2 C3 C4 120.22(14) yes . . .
C2 C3 C4 121.11(12) yes . . .
C3 C4 C5 120.20(15) yes . . .
C4 C5 C6 118.91(12) yes . . .
C4 C5 C7 120.33(14) yes . . .
C6 C5 C7 120.73(11) yes . . .
C1 C6 C5 120.18(12) yes . . .
C5 C7 C8 120.96(11) yes . . .
C5 C7 C12 120.56(14) yes . . .
C8 C7 C12 118.48(12) yes . . .
C7 C8 C9 121.12(12) yes . . .
C8 C9 C10 120.67(16) yes . . .
C9 C10 C11 117.36(13) yes . . .
F1 C11 C10 118.61(11) yes . . .
F1 C11 C12 117.71(14) yes . . .
C10 C11 C12 123.67(12) yes . . .
C7 C12 C11 118.70(15) yes . . .
N1 C13 C14 111.03(13) yes . . .
N1 C13 C15 107.69(15) yes . . .
N1 C13 C16 107.69(13) yes . . .
C14 C13 C15 109.08(13) yes . . .
C14 C13 C16 111.10(15) yes . . .
C15 C13 C16 110.19(14) yes . . .
N2 C17 C18 109.83(10) yes . . .
N2 C17 C19 107.40(13) yes . . .
N2 C17 C20 109.11(16) yes . . .
C18 C17 C19 110.70(18) yes . . .
C18 C17 C20 109.92(14) yes . . .
C19 C17 C20 109.83(11) yes . . .
C1 C2 H1 119.3(11) no . . .
C3 C2 H1 122.1(11) no . . .
C3 C4 H2 119.3(8) no . . .
C5 C4 H2 120.5(8) no . . .
C1 C6 H3 120.8(11) no . . .
C5 C6 H3 119.0(11) no . . .
C7 C8 H4 116.9(10) no . . .
C9 C8 H4 122.0(10) no . . .
C8 C9 H5 120.6(7) no . . .
C10 C9 H5 118.8(7) no . . .
C9 C10 H6 121.6(11) no . . .
C11 C10 H6 121.1(11) no . . .
C7 C12 H7 122.3(7) no . . .
C11 C12 H7 118.9(7) no . . .
C13 C14 H8 114.2(8) no . . .
C13 C14 H9 106.8(8) no . . .
C13 C14 H10 110.8(11) no . . .
H8 C14 H9 108.4(18) no . . .
H8 C14 H10 106.0(17) no . . .
H9 C14 H10 110.6(17) no . . .
C13 C15 H11 108.5(11) no . . .
C13 C15 H12 110.3(12) no . . .
C13 C15 H13 106.4(11) no . . .
H11 C15 H12 113.2(16) no . . .
H11 C15 H13 107.7(16) no . . .
H12 C15 H13 110.5(16) no . . .
C13 C16 H14 110.9(13) no . . .
C13 C16 H15 110.3(10) no . . .
C13 C16 H16 112.4(11) no . . .
H14 C16 H15 106.4(17) no . . .
H14 C16 H16 106.6(15) no . . .
H15 C16 H16 110.1(18) no . . .
C17 C18 H17 108.7(10) no . . .
C17 C18 H18 112.3(12) no . . .
C17 C18 H19 109.7(15) no . . .
H17 C18 H18 110.0(18) no . . .
H17 C18 H19 107.6(18) no . . .
H18 C18 H19 108.4(15) no . . .
C17 C19 H20 110.2(11) no . . .
C17 C19 H21 109.3(13) no . . .
C17 C19 H22 109.6(13) no . . .
H20 C19 H21 109.1(19) no . . .
H20 C19 H22 108.7(17) no . . .
H21 C19 H22 110.0(14) no . . .
C17 C20 H23 109.3(9) no . . .
C17 C20 H24 113.4(12) no . . .
C17 C20 H25 108.8(12) no . . .
H23 C20 H24 110.7(19) no . . .
H23 C20 H25 106.3(16) no . . .
H24 C20 H25 108.1(14) 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 C11 1.3605(14) yes . .
O1 N1 1.2899(17) yes . .
O2 N2 1.2915(18) yes . .
N1 C1 1.436(2) yes . .
N1 C13 1.509(3) yes . .
N2 C3 1.4460(16) yes . .
N2 C17 1.513(2) yes . .
C1 C2 1.3956(18) yes . .
C1 C6 1.3844(18) yes . .
C2 C3 1.384(3) yes . .
C3 C4 1.3893(18) yes . .
C4 C5 1.3951(18) yes . .
C5 C6 1.401(3) yes . .
C5 C7 1.4885(17) yes . .
C7 C8 1.398(3) yes . .
C7 C12 1.3985(16) yes . .
C8 C9 1.3826(19) yes . .
C9 C10 1.3886(18) yes . .
C10 C11 1.377(3) yes . .
C11 C12 1.3775(19) yes . .
C13 C14 1.5243(16) yes . .
C13 C15 1.518(3) yes . .
C13 C16 1.527(3) yes . .
C17 C18 1.519(3) yes . .
C17 C19 1.530(3) yes . .
C17 C20 1.517(3) yes . .
C2 H1 0.949(15) no . .
C4 H2 0.93(2) no . .
C6 H3 0.908(14) no . .
C8 H4 0.977(12) no . .
C9 H5 0.983(19) no . .
C10 H6 0.933(17) no . .
C12 H7 0.989(19) no . .
C14 H8 0.939(19) no . .
C14 H9 1.01(3) no . .
C14 H10 0.98(3) no . .
C15 H11 0.994(14) no . .
C15 H12 0.97(2) no . .
C15 H13 0.97(3) no . .
C16 H14 0.964(15) no . .
C16 H15 0.98(3) no . .
C16 H16 1.00(2) no . .
C18 H17 1.00(2) no . .
C18 H18 0.978(19) no . .
C18 H19 1.00(3) no . .
C19 H20 1.02(2) no . .
C19 H21 0.95(2) no . .
C19 H22 1.04(3) no . .
C20 H23 0.97(2) no . .
C20 H24 0.99(2) no . .
C20 H25 0.99(2) 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
O1 C2 2.735(2) no . .
O1 C6 3.5176(18) no . .
O1 C14 3.568(2) no . .
O1 C15 2.626(3) no . .
O1 C16 3.288(3) no . .
O2 C2 2.8379(19) no . .
O2 C4 3.4468(16) no . .
O2 C19 2.962(3) no . .
O2 C20 2.814(2) no . .
C1 C4 2.771(3) no . .
C1 C14 3.196(3) no . .
C1 C16 2.943(3) no . .
C2 C5 2.8065(18) no . .
C2 C13 3.584(3) no . .
C2 C16 3.580(3) no . .
C2 C17 3.409(2) no . .
C2 C19 3.4083(19) no . .
C3 C6 2.7711(17) no . .
C3 C18 2.917(3) no . .
C3 C19 3.1420(19) no . .
C4 C8 2.9816(19) no . .
C4 C17 3.3403(15) no . .
C4 C18 3.111(2) no . .
C6 C12 2.9741(18) no . .
C6 C13 3.201(3) no . .
C6 C14 3.190(3) no . .
C6 C16 3.592(3) no . .
C7 C10 2.8137(19) no . .
C8 C11 2.7270(17) no . .
C9 C12 2.780(3) no . .
F1 O1 3.5477(18) no . 1_665
F1 C12 3.392(3) no . 2_676
F1 C14 3.3400(17) no . 2_676
F1 C18 3.4827(19) no . 1_666
O1 F1 3.5477(18) no . 1_445
O1 C6 3.2723(16) no . 2_566
O1 C10 3.503(3) no . 1_445
O1 C14 3.517(3) no . 2_566
O2 O2 2.6706(15) no . 2_555
O2 N2 2.3487(19) no . 2_555
O2 C3 3.019(2) no . 2_555
O2 C4 3.043(2) no . 2_555
O2 C9 3.280(2) no . 1_445
O2 C17 3.167(3) no . 2_555
O2 C18 3.548(3) no . 2_555
O2 C20 3.2274(19) no . 2_555
N1 N1 3.4654(16) no . 2_566
N2 O2 2.3487(19) no . 2_555
N2 N2 2.690(3) no . 2_555
N2 C3 3.526(3) no . 2_555
N2 C20 3.506(3) no . 2_555
C3 O2 3.019(2) no . 2_555
C3 N2 3.526(3) no . 2_555
C3 C20 3.342(3) no . 2_555
C4 O2 3.043(2) no . 2_555
C4 C20 3.450(3) no . 2_555
C6 O1 3.2723(16) no . 2_566
C9 O2 3.280(2) no . 1_665
C10 O1 3.503(3) no . 1_665
C12 F1 3.392(3) no . 2_676
C14 F1 3.3400(17) no . 2_676
C14 O1 3.517(3) no . 2_566
C15 C15 3.236(3) no . 2_466
C17 O2 3.167(3) no . 2_555
C18 F1 3.4827(19) no . 1_444
C18 O2 3.548(3) no . 2_555
C20 O2 3.2274(19) no . 2_555
C20 N2 3.506(3) no . 2_555
C20 C3 3.342(3) no . 2_555
C20 C4 3.450(3) no . 2_555
F1 H6 2.54(2) no . .
F1 H7 2.512(14) no . .
O1 H1 2.463(17) no . .
O1 H10 3.556(18) no . .
O1 H11 2.44(3) no . .
O1 H12 2.68(2) no . .
O1 H13 3.57(3) no . .
O1 H14 3.14(3) no . .
O2 H1 2.69(2) no . .
O2 H20 3.33(3) no . .
O2 H22 2.65(3) no . .
O2 H23 3.088(19) no . .
O2 H24 2.576(16) no . .
N1 H1 2.559(16) no . .
N1 H3 2.642(15) no . .
N1 H8 2.824(18) no . .
N1 H9 3.34(3) no . .
N1 H10 2.628(17) no . .
N1 H11 2.63(2) no . .
N1 H12 2.66(2) no . .
N1 H13 3.26(3) no . .
N1 H14 2.63(3) no . .
N1 H15 3.31(3) no . .
N1 H16 2.69(3) no . .
N2 H1 2.624(19) no . .
N2 H2 2.610(14) no . .
N2 H17 3.34(3) no . .
N2 H18 2.72(3) no . .
N2 H19 2.68(3) no . .
N2 H20 2.68(3) no . .
N2 H21 3.28(2) no . .
N2 H22 2.630(18) no . .
N2 H23 2.685(18) no . .
N2 H24 2.705(15) no . .
N2 H25 3.324(16) no . .
C1 H8 3.084(19) no . .
C1 H10 3.37(2) no . .
C1 H14 3.13(3) no . .
C1 H16 2.67(3) no . .
C2 H2 3.250(19) no . .
C2 H3 3.239(13) no . .
C2 H14 3.41(3) no . .
C2 H16 3.25(3) no . .
C2 H18 3.51(2) no . .
C2 H20 2.858(19) no . .
C2 H22 3.507(14) no . .
C3 H18 2.65(3) no . .
C3 H19 3.11(3) no . .
C3 H20 2.87(2) no . .
C3 H22 3.45(3) no . .
C4 H1 3.281(17) no . .
C4 H3 3.223(16) no . .
C4 H4 2.663(17) no . .
C4 H18 2.704(19) no . .
C4 H19 2.970(19) no . .
C5 H4 2.637(18) no . .
C5 H7 2.721(12) no . .
C5 H18 3.600(15) no . .
C6 H1 3.267(13) no . .
C6 H2 3.257(19) no . .
C6 H7 2.736(13) no . .
C6 H8 2.73(3) no . .
C6 H10 3.28(3) no . .
C6 H16 3.07(3) no . .
C7 H2 2.664(14) no . .
C7 H3 2.647(18) no . .
C7 H5 3.311(18) no . .
C8 H2 2.718(15) no . .
C8 H6 3.256(14) no . .
C8 H7 3.316(18) no . .
C10 H4 3.301(11) no . .
C10 H7 3.303(18) no . .
C11 H5 3.251(17) no . .
C12 H3 2.689(16) no . .
C12 H4 3.271(15) no . .
C12 H6 3.265(19) no . .
C13 H3 3.106(17) no . .
C14 H3 2.687(19) no . .
C14 H11 3.335(15) no . .
C14 H12 2.65(2) no . .
C14 H13 2.635(17) no . .
C14 H14 3.353(13) no . .
C14 H15 2.739(17) no . .
C14 H16 2.761(16) no . .
C15 H8 3.316(17) no . .
C15 H9 2.560(18) no . .
C15 H10 2.764(17) no . .
C15 H14 2.695(18) no . .
C15 H15 2.69(3) no . .
C15 H16 3.38(2) no . .
C16 H8 2.678(13) no . .
C16 H9 2.777(15) no . .
C16 H10 3.356(17) no . .
C16 H11 2.65(2) no . .
C16 H12 3.34(2) no . .
C16 H13 2.636(19) no . .
C17 H1 3.484(17) no . .
C17 H2 3.333(13) no . .
C18 H2 2.915(16) no . .
C18 H20 2.70(3) no . .
C18 H21 2.708(17) no . .
C18 H22 3.402(19) no . .
C18 H23 2.64(3) no . .
C18 H24 3.37(2) no . .
C18 H25 2.669(15) no . .
C19 H1 3.164(15) no . .
C19 H17 2.73(2) no . .
C19 H18 2.717(16) no . .
C19 H19 3.38(3) no . .
C19 H23 3.33(3) no . .
C19 H24 2.72(3) no . .
C19 H25 2.69(2) no . .
C20 H17 2.65(3) no . .
C20 H18 3.351(19) no . .
C20 H19 2.690(19) no . .
C20 H20 3.38(3) no . .
C20 H21 2.66(3) no . .
C20 H22 2.72(3) no . .
H1 H14 3.27(4) no . .
H1 H16 3.55(3) no . .
H1 H20 2.67(3) no . .
H1 H22 3.02(2) no . .
H2 H4 2.21(3) no . .
H2 H18 2.71(3) no . .
H2 H19 2.48(3) no . .
H3 H7 2.26(2) no . .
H3 H8 2.17(3) no . .
H3 H10 2.65(3) no . .
H3 H16 3.29(3) no . .
H4 H5 2.40(2) no . .
H4 H18 3.572(19) no . .
H4 H19 3.471(18) no . .
H5 H6 2.351(19) no . .
H8 H12 3.56(3) no . .
H8 H13 3.46(3) no . .
H8 H14 3.581(18) no . .
H8 H15 2.94(3) no . .
H8 H16 2.573(19) no . .
H9 H11 3.48(3) no . .
H9 H12 2.79(3) no . .
H9 H13 2.34(3) no . .
H9 H15 2.64(2) no . .
H9 H16 3.16(3) no . .
H10 H12 2.58(3) no . .
H10 H13 3.07(3) no . .
H11 H14 2.47(3) no . .
H11 H15 2.91(3) no . .
H11 H16 3.57(3) no . .
H12 H14 3.59(3) no . .
H12 H15 3.58(3) no . .
H13 H14 2.93(3) no . .
H13 H15 2.46(3) no . .
H13 H16 3.56(3) no . .
H14 H20 3.51(3) no . .
H17 H20 3.03(3) no . .
H17 H21 2.57(3) no . .
H17 H23 2.87(4) no . .
H17 H24 3.57(4) no . .
H17 H25 2.44(3) no . .
H18 H20 2.53(3) no . .
H18 H21 3.00(2) no . .
H18 H23 3.55(3) no . .
H18 H25 3.57(3) no . .
H19 H23 2.46(3) no . .
H19 H25 2.98(2) no . .
H21 H23 3.54(4) no . .
H21 H24 2.96(4) no . .
H21 H25 2.49(3) no . .
H22 H24 2.56(4) no . .
H22 H25 3.04(3) no . .
F1 H3 3.129(16) no . 2_676
F1 H7 3.03(2) no . 2_676
F1 H8 2.697(14) no . 2_676
F1 H9 3.19(3) no . 1_655
F1 H10 3.208(19) no . 2_676
F1 H17 2.516(17) no . 1_666
F1 H21 3.55(2) no . 1_666
F1 H25 2.87(3) no . 1_666
O1 H3 2.625(16) no . 2_566
O1 H6 3.11(3) no . 1_445
O1 H7 2.743(19) no . 2_566
O1 H8 3.51(3) no . 2_566
O1 H10 2.71(3) no . 2_566
O1 H21 3.026(14) no . 2_455
O1 H22 3.545(16) no . 2_455
O2 H2 2.54(2) no . 2_555
O2 H5 2.439(17) no . 1_445
O2 H6 3.19(2) no . 1_445
O2 H19 3.00(3) no . 2_555
O2 H23 2.664(16) no . 2_555
O2 H24 3.508(15) no . 2_555
N1 H3 3.275(19) no . 2_566
N1 H10 3.10(3) no . 2_566
N2 H5 3.531(18) no . 1_445
N2 H23 3.08(2) no . 2_555
N2 H24 3.418(19) no . 2_555
C1 H10 3.09(3) no . 2_566
C1 H12 3.45(2) no . 2_566
C2 H6 3.19(3) no . 1_445
C2 H10 3.38(3) no . 2_566
C2 H23 3.14(3) no . 2_555
C3 H23 2.86(3) no . 2_555
C3 H24 3.04(3) no . 2_555
C4 H23 3.30(3) no . 2_555
C4 H24 2.77(3) no . 2_555
C5 H12 3.16(3) no . 2_566
C5 H17 3.56(3) no . 2_565
C5 H18 3.31(3) no . 2_565
C5 H24 3.34(3) no . 2_555
C6 H12 2.96(3) no . 2_566
C6 H17 3.27(3) no . 2_565
C6 H18 3.42(3) no . 2_565
C7 H12 3.56(3) no . 2_566
C7 H15 3.20(3) no . 1_655
C7 H17 3.45(3) no . 2_565
C7 H18 3.43(3) no . 2_565
C8 H14 3.55(2) no . 2_565
C8 H15 2.94(3) no . 1_655
C8 H16 3.372(18) no . 2_565
C8 H20 3.07(3) no . 2_565
C8 H21 3.52(3) no . 2_565
C9 H1 3.434(18) no . 1_665
C9 H15 2.89(3) no . 1_655
C9 H20 3.09(3) no . 2_565
C9 H21 3.31(3) no . 2_565
C10 H1 3.15(2) no . 1_665
C10 H9 3.46(3) no . 1_655
C10 H10 3.49(3) no . 2_676
C10 H15 3.11(3) no . 1_655
C10 H19 3.58(3) no . 2_665
C10 H21 3.27(3) no . 2_565
C11 H9 3.25(3) no . 1_655
C11 H13 3.46(3) no . 1_655
C11 H15 3.32(3) no . 1_655
C11 H21 3.41(3) no . 2_565
C12 H11 3.60(2) no . 2_566
C12 H12 3.32(2) no . 2_566
C12 H13 3.15(3) no . 1_655
C12 H15 3.39(3) no . 1_655
C12 H17 3.58(3) no . 2_565
C14 H6 3.355(13) no . 2_676
C14 H17 3.36(2) no . 2_565
C14 H19 3.59(3) no . 2_565
C14 H23 3.488(18) no . 1_566
C14 H25 3.58(2) no . 1_566
C15 H7 3.21(2) no . 2_566
C15 H11 3.15(2) no . 2_466
C15 H12 3.25(2) no . 2_466
C15 H13 2.819(19) no . 2_466
C15 H24 3.49(3) no . 2_455
C15 H25 3.364(17) no . 1_566
C15 H25 3.542(14) no . 2_455
C16 H4 3.018(17) no . 2_565
C16 H19 3.42(3) no . 2_565
C16 H22 3.525(17) no . 2_455
C18 H3 3.59(2) no . 2_565
C18 H8 3.06(2) no . 2_565
C18 H16 3.239(17) no . 2_565
C19 H1 3.495(18) no . 2_455
C19 H11 3.599(15) no . 2_455
C19 H14 3.478(19) no . 2_455
C20 H2 3.53(3) no . 2_555
C20 H9 3.45(2) no . 1_544
C20 H11 3.066(14) no . 2_455
C20 H12 3.316(17) no . 1_544
C20 H13 3.518(14) no . 1_544
H1 C9 3.434(18) no . 1_445
H1 C10 3.15(2) no . 1_445
H1 C19 3.495(18) no . 2_455
H1 H5 3.16(3) no . 1_445
H1 H6 2.65(4) no . 1_445
H1 H10 3.49(3) no . 2_566
H1 H20 3.57(3) no . 2_455
H1 H21 3.24(3) no . 2_455
H1 H22 3.10(3) no . 2_455
H1 H23 3.40(4) no . 2_555
H2 O2 2.54(2) no . 2_555
H2 C20 3.53(3) no . 2_555
H2 H5 2.94(3) no . 2_665
H2 H16 3.53(3) no . 2_565
H2 H23 3.60(3) no . 2_555
H2 H24 2.76(4) no . 2_555
H3 F1 3.129(16) no . 2_676
H3 O1 2.625(16) no . 2_566
H3 N1 3.275(19) no . 2_566
H3 C18 3.59(2) no . 2_565
H3 H12 3.00(4) no . 2_566
H3 H17 2.90(4) no . 2_565
H3 H18 3.48(3) no . 2_565
H4 C16 3.018(17) no . 2_565
H4 H5 3.51(3) no . 2_665
H4 H14 2.92(3) no . 2_565
H4 H15 3.38(3) no . 1_655
H4 H15 3.07(3) no . 2_565
H4 H16 2.49(3) no . 2_565
H4 H20 3.20(4) no . 2_565
H5 O2 2.439(17) no . 1_665
H5 N2 3.531(18) no . 1_665
H5 H1 3.16(3) no . 1_665
H5 H2 2.94(3) no . 2_665
H5 H4 3.51(3) no . 2_665
H5 H14 3.01(3) no . 2_565
H5 H15 3.33(4) no . 1_655
H5 H19 3.32(4) no . 2_665
H5 H20 3.22(4) no . 2_565
H5 H22 2.97(4) no . 1_665
H6 O1 3.11(3) no . 1_665
H6 O2 3.19(2) no . 1_665
H6 C2 3.19(3) no . 1_665
H6 C14 3.355(13) no . 2_676
H6 H1 2.65(4) no . 1_665
H6 H8 3.41(2) no . 2_676
H6 H9 3.54(4) no . 1_655
H6 H9 3.40(3) no . 2_676
H6 H10 2.709(19) no . 2_676
H6 H19 3.23(4) no . 2_665
H6 H23 2.90(3) no . 2_665
H7 F1 3.03(2) no . 2_676
H7 O1 2.743(19) no . 2_566
H7 C15 3.21(2) no . 2_566
H7 H11 2.85(3) no . 2_566
H7 H12 2.75(3) no . 2_566
H7 H13 3.14(4) no . 1_655
H7 H21 3.59(3) no . 1_666
H7 H25 3.37(3) no . 1_666
H8 F1 2.697(14) no . 2_676
H8 O1 3.51(3) no . 2_566
H8 C18 3.06(2) no . 2_565
H8 H6 3.41(2) no . 2_676
H8 H17 2.43(3) no . 2_565
H8 H18 3.42(3) no . 2_565
H8 H19 2.87(4) no . 2_565
H9 F1 3.19(3) no . 1_455
H9 C10 3.46(3) no . 1_455
H9 C11 3.25(3) no . 1_455
H9 C20 3.45(2) no . 1_566
H9 H6 3.54(4) no . 1_455
H9 H6 3.40(3) no . 2_676
H9 H23 3.09(3) no . 1_566
H9 H25 2.87(3) no . 1_566
H10 F1 3.208(19) no . 2_676
H10 O1 2.71(3) no . 2_566
H10 N1 3.10(3) no . 2_566
H10 C1 3.09(3) no . 2_566
H10 C2 3.38(3) no . 2_566
H10 C10 3.49(3) no . 2_676
H10 H1 3.49(3) no . 2_566
H10 H6 2.709(19) no . 2_676
H10 H23 3.01(3) no . 1_566
H10 H25 3.50(4) no . 1_566
H11 C12 3.60(2) no . 2_566
H11 C15 3.15(2) no . 2_466
H11 C19 3.599(15) no . 2_455
H11 C20 3.066(14) no . 2_455
H11 H7 2.85(3) no . 2_566
H11 H11 3.36(3) no . 2_466
H11 H12 3.04(3) no . 2_466
H11 H13 2.61(3) no . 2_466
H11 H21 3.18(3) no . 2_455
H11 H22 3.31(2) no . 2_455
H11 H24 2.65(3) no . 2_455
H11 H25 2.61(2) no . 2_455
H12 C1 3.45(2) no . 2_566
H12 C5 3.16(3) no . 2_566
H12 C6 2.96(3) no . 2_566
H12 C7 3.56(3) no . 2_566
H12 C12 3.32(2) no . 2_566
H12 C15 3.25(2) no . 2_466
H12 C20 3.316(17) no . 1_566
H12 H3 3.00(4) no . 2_566
H12 H7 2.75(3) no . 2_566
H12 H11 3.04(3) no . 2_466
H12 H12 3.54(3) no . 2_466
H12 H13 2.72(3) no . 2_466
H12 H23 3.27(2) no . 1_566
H12 H24 3.01(3) no . 1_566
H12 H25 3.06(3) no . 1_566
H13 C11 3.46(3) no . 1_455
H13 C12 3.15(3) no . 1_455
H13 C15 2.819(19) no . 2_466
H13 C20 3.518(14) no . 1_566
H13 H7 3.14(4) no . 1_455
H13 H11 2.61(3) no . 2_466
H13 H12 2.72(3) no . 2_466
H13 H13 2.70(3) no . 2_466
H13 H24 3.48(3) no . 1_566
H13 H24 3.471(18) no . 2_455
H13 H25 2.83(2) no . 1_566
H14 C8 3.55(2) no . 2_565
H14 C19 3.478(19) no . 2_455
H14 H4 2.92(3) no . 2_565
H14 H5 3.01(3) no . 2_565
H14 H21 3.56(3) no . 2_455
H14 H22 2.58(3) no . 2_455
H14 H24 3.14(3) no . 2_455
H15 C7 3.20(3) no . 1_455
H15 C8 2.94(3) no . 1_455
H15 C9 2.89(3) no . 1_455
H15 C10 3.11(3) no . 1_455
H15 C11 3.32(3) no . 1_455
H15 C12 3.39(3) no . 1_455
H15 H4 3.38(3) no . 1_455
H15 H4 3.07(3) no . 2_565
H15 H5 3.33(4) no . 1_455
H15 H19 3.30(3) no . 2_565
H16 C8 3.372(18) no . 2_565
H16 C18 3.239(17) no . 2_565
H16 H2 3.53(3) no . 2_565
H16 H4 2.49(3) no . 2_565
H16 H17 3.36(2) no . 2_565
H16 H18 3.04(3) no . 2_565
H16 H19 2.75(3) no . 2_565
H17 F1 2.516(17) no . 1_444
H17 C5 3.56(3) no . 2_565
H17 C6 3.27(3) no . 2_565
H17 C7 3.45(3) no . 2_565
H17 C12 3.58(3) no . 2_565
H17 C14 3.36(2) no . 2_565
H17 H3 2.90(4) no . 2_565
H17 H8 2.43(3) no . 2_565
H17 H16 3.36(2) no . 2_565
H18 C5 3.31(3) no . 2_565
H18 C6 3.42(3) no . 2_565
H18 C7 3.43(3) no . 2_565
H18 H3 3.48(3) no . 2_565
H18 H8 3.42(3) no . 2_565
H18 H16 3.04(3) no . 2_565
H19 O2 3.00(3) no . 2_555
H19 C10 3.58(3) no . 2_665
H19 C14 3.59(3) no . 2_565
H19 C16 3.42(3) no . 2_565
H19 H5 3.32(4) no . 2_665
H19 H6 3.23(4) no . 2_665
H19 H8 2.87(4) no . 2_565
H19 H15 3.30(3) no . 2_565
H19 H16 2.75(3) no . 2_565
H20 C8 3.07(3) no . 2_565
H20 C9 3.09(3) no . 2_565
H20 H1 3.57(3) no . 2_455
H20 H4 3.20(4) no . 2_565
H20 H5 3.22(4) no . 2_565
H20 H22 3.18(3) no . 2_455
H21 F1 3.55(2) no . 1_444
H21 O1 3.026(14) no . 2_455
H21 C8 3.52(3) no . 2_565
H21 C9 3.31(3) no . 2_565
H21 C10 3.27(3) no . 2_565
H21 C11 3.41(3) no . 2_565
H21 H1 3.24(3) no . 2_455
H21 H7 3.59(3) no . 1_444
H21 H11 3.18(3) no . 2_455
H21 H14 3.56(3) no . 2_455
H22 O1 3.545(16) no . 2_455
H22 C16 3.525(17) no . 2_455
H22 H1 3.10(3) no . 2_455
H22 H5 2.97(4) no . 1_445
H22 H11 3.31(2) no . 2_455
H22 H14 2.58(3) no . 2_455
H22 H20 3.18(3) no . 2_455
H22 H22 3.43(3) no . 2_455
H23 O2 2.664(16) no . 2_555
H23 N2 3.08(2) no . 2_555
H23 C2 3.14(3) no . 2_555
H23 C3 2.86(3) no . 2_555
H23 C4 3.30(3) no . 2_555
H23 C14 3.488(18) no . 1_544
H23 H1 3.40(4) no . 2_555
H23 H2 3.60(3) no . 2_555
H23 H6 2.90(3) no . 2_665
H23 H9 3.09(3) no . 1_544
H23 H10 3.01(3) no . 1_544
H23 H12 3.27(2) no . 1_544
H24 O2 3.508(15) no . 2_555
H24 N2 3.418(19) no . 2_555
H24 C3 3.04(3) no . 2_555
H24 C4 2.77(3) no . 2_555
H24 C5 3.34(3) no . 2_555
H24 C15 3.49(3) no . 2_455
H24 H2 2.76(4) no . 2_555
H24 H11 2.65(3) no . 2_455
H24 H12 3.01(3) no . 1_544
H24 H13 3.48(3) no . 1_544
H24 H13 3.471(18) no . 2_455
H24 H14 3.14(3) no . 2_455
H25 F1 2.87(3) no . 1_444
H25 C14 3.58(2) no . 1_544
H25 C15 3.364(17) no . 1_544
H25 C15 3.542(14) no . 2_455
H25 H7 3.37(3) no . 1_444
H25 H9 2.87(3) no . 1_544
H25 H10 3.50(4) no . 1_544
H25 H11 2.61(2) no . 2_455
H25 H12 3.06(3) no . 1_544
H25 H13 2.83(2) no . 1_544
O1 O1 4.3486(11) no . 2_566
O1 N1 3.7143(13) no . 2_566
N1 O1 3.7143(13) no . 2_566
N1 N1 3.4654(16) 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 35.47(19) no . . . .
O1 N1 C1 C6 -144.25(13) no . . . .
O1 N1 C13 C14 135.45(10) no . . . .
O1 N1 C13 C15 16.09(12) no . . . .
O1 N1 C13 C16 -102.72(12) no . . . .
C1 N1 C13 C14 -71.56(13) no . . . .
C1 N1 C13 C15 169.08(8) no . . . .
C1 N1 C13 C16 50.27(12) no . . . .
C13 N1 C1 C2 -118.21(13) no . . . .
C13 N1 C1 C6 62.07(17) no . . . .
O2 N2 C3 C2 -48.8(2) no . . . .
O2 N2 C3 C4 130.05(14) no . . . .
O2 N2 C17 C18 -169.92(12) no . . . .
O2 N2 C17 C19 69.63(16) no . . . .
O2 N2 C17 C20 -49.37(16) no . . . .
C3 N2 C17 C18 45.48(17) no . . . .
C3 N2 C17 C19 -74.97(14) no . . . .
C3 N2 C17 C20 166.03(11) no . . . .
C17 N2 C3 C2 96.21(16) no . . . .
C17 N2 C3 C4 -84.93(18) no . . . .
N1 C1 C2 C3 177.61(14) no . . . .
N1 C1 C6 C5 -178.52(14) no . . . .
C2 C1 C6 C5 1.8(3) no . . . .
C6 C1 C2 C3 -2.7(3) no . . . .
C1 C2 C3 N2 -179.18(15) no . . . .
C1 C2 C3 C4 2.0(3) no . . . .
N2 C3 C4 C5 -179.20(14) no . . . .
C2 C3 C4 C5 -0.4(3) no . . . .
C3 C4 C5 C6 -0.6(3) no . . . .
C3 C4 C5 C7 177.18(15) no . . . .
C4 C5 C6 C1 -0.1(3) no . . . .
C4 C5 C7 C8 30.8(3) no . . . .
C4 C5 C7 C12 -149.40(16) no . . . .
C6 C5 C7 C8 -151.46(16) no . . . .
C6 C5 C7 C12 28.3(3) no . . . .
C7 C5 C6 C1 -177.87(15) no . . . .
C5 C7 C8 C9 179.98(16) no . . . .
C5 C7 C12 C11 -179.70(16) no . . . .
C8 C7 C12 C11 0.1(3) no . . . .
C12 C7 C8 C9 0.2(3) no . . . .
C7 C8 C9 C10 -0.2(3) no . . . .
C8 C9 C10 C11 -0.1(3) no . . . .
C9 C10 C11 F1 179.34(17) no . . . .
C9 C10 C11 C12 0.4(3) no . . . .
F1 C11 C12 C7 -179.35(15) no . . . .
C10 C11 C12 C7 -0.4(3) no . . . .
