#------------------------------------------------------------------------------
#$Date: 2023-05-05 06:19:02 +0300 (Fri, 05 May 2023) $
#$Revision: 283458 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/92/7159243.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_7159243
loop_
_publ_author_name
'Galenko, Ekaterina E.'
'Zanakhov, Timur O.'
'Novikov, Mikhail S.'
'Khlebnikov, Alexander F.'
_publ_section_title
;
 Metal carbonyl mediated rearrangement of
 5-(2-oxoalkyl)-1,2,4-oxadiazoles: synthesis of fully substituted
 pyrimidines.
;
_journal_issue                   14
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2990
_journal_page_last               3001
_journal_paper_doi               10.1039/d3ob00148b
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C20 H17 F N2 O4'
_chemical_formula_sum            'C20 H17 F N2 O4'
_chemical_formula_weight         368.35
_chemical_name_systematic
'ethyl 4-(4-fluorophenyl)-2-(4-methoxyphenyl)-6-oxo-1,6-dihydropyrimidine-5-carboxylate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-12-16
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-01-17 deposited with the CCDC.	2023-03-13 downloaded from the CCDC.
;
_cell_angle_alpha                96.374(5)
_cell_angle_beta                 91.813(6)
_cell_angle_gamma                107.232(6)
_cell_formula_units_Z            2
_cell_length_a                   7.0037(5)
_cell_length_b                   8.0678(4)
_cell_length_c                   16.6349(10)
_cell_measurement_reflns_used    3868
_cell_measurement_temperature    100.00(17)
_cell_measurement_theta_max      75.8160
_cell_measurement_theta_min      5.3240
_cell_volume                     890.14(10)
_computing_cell_refinement       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(17)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -54.00  33.00   1.00    1.00    --  -41.44  38.00 -90.00   87
  2  ω   -115.00 -13.00   1.00    1.00    --  -41.44 -57.00 120.00  102
  3  ω     32.00  63.00   1.00    1.00    --   41.44 -99.00  90.00   31
  4  ω    -21.00  73.00   1.00    1.00    --   41.44 -77.00   0.00   94
  5  ω     68.00 128.00   1.00    1.00    --   41.44-178.00  60.00   60
  6  ω     41.00 105.00   1.00    2.00    --  112.00 -95.00 -90.00   64
  7  ω    110.00 169.00   1.00    2.00    --  112.00  77.00-180.00   59
  8  ω     55.00  91.00   1.00    2.00    --  112.00 -45.00-120.00   36
  9  ω    110.00 139.00   1.00    2.00    --  112.00  77.00 150.00   29
 10  ω     82.00 112.00   1.00    2.00    --  112.00-126.00  60.00   30
 11  ω    142.00 176.00   1.00    2.00    --  112.00  77.00 150.00   34
 12  ω     39.00 113.00   1.00    2.00    --  112.00-126.00  30.00   74
 13  ω    138.00 168.00   1.00    2.00    --  112.00 126.00-180.00   30
 14  ω    115.00 173.00   1.00    2.00    --  112.00  77.00-150.00   58
 15  ω     40.00 112.00   1.00    2.00    --  112.00-126.00-180.00   72
 16  ω     55.00  80.00   1.00    2.00    --  112.00 -95.00 150.00   25
 17  ω     74.00 112.00   1.00    2.00    --  112.00-126.00 -90.00   38
 18  ω     85.00 178.00   1.00    2.00    --  112.00  30.00 -60.00   93
 19  ω     41.00 135.00   1.00    2.00    --  112.00 -45.00 120.00   94
 20  ω     79.00 113.00   1.00    2.00    --  112.00-126.00-120.00   34
 21  ω     45.00  70.00   1.00    2.00    --  112.00-126.00   0.00   25
 22  ω     40.00 125.00   1.00    2.00    --  112.00-142.00 158.45   85
 23  ω    -16.00  20.00   1.00    1.00    --    2.00  16.00  78.56   36
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0387811000
_diffrn_orient_matrix_UB_12      -0.1545585000
_diffrn_orient_matrix_UB_13      -0.0679513000
_diffrn_orient_matrix_UB_21      0.2275333000
_diffrn_orient_matrix_UB_22      0.0336214000
_diffrn_orient_matrix_UB_23      -0.0042528000
_diffrn_orient_matrix_UB_31      -0.0031605000
_diffrn_orient_matrix_UB_32      -0.1248901000
_diffrn_orient_matrix_UB_33      0.0639418000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6796
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.488
_diffrn_reflns_theta_min         2.679
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.869
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_description       prism
_exptl_crystal_F_000             384
_exptl_crystal_preparation       'slove evaporation of metanol solution'
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3509
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0525
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0872P)²+0.1565P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1527
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2891
_reflns_number_total             3509
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00148b2.cif
_cod_data_source_block           176
_cod_depositor_comments
'Adding full bibliography for 7159243--7159244.cif.'
_cod_database_code               7159243
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 H17 F N2 O4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.966
_shelx_estimated_absorpt_t_min   0.873
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C0) = Uanis(C7)
3. Others
 Fixed Sof: H6BC(0.5) H6BD(0.5) H6AA(0.5) H6AB(0.5) C0(0.5) H0A(0.5) H0B(0.5)
 H0C(0.5) C7(0.5) H7A(0.5) H7B(0.5) H7C(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C6(H6BC,H6BD), C6(H6AA,H6AB)
4.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C16(H16), C11(H11), C18(H18), C12(H12), C9(H9), C15(H15), C19(H19),
 C8(H8)
4.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C0(H0A,H0B,H0C), C7(H7A,H7B,H7C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.149
_oxdiff_exptl_absorpt_empirical_full_min 0.394
loop_
_space_group_symop_operation_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
F001 F 1.08377(19) 0.82114(14) 0.99090(7) 0.0334(3) Uani 1 1 d . . . . .
O3 O 0.54101(18) 0.21130(14) 0.81568(7) 0.0204(3) Uani 1 1 d . . . . .
O4 O 0.81839(19) 0.79452(15) 0.29035(8) 0.0211(3) Uani 1 1 d . . . . .
O2 O 0.6713(2) 0.00037(16) 0.76738(8) 0.0284(3) Uani 1 1 d . . . . .
O1 O 0.5221(2) -0.02052(15) 0.59642(8) 0.0244(3) Uani 1 1 d . . . . .
N2 N 0.7973(2) 0.50341(17) 0.63049(9) 0.0161(3) Uani 1 1 d . . . . .
N1 N 0.6407(2) 0.23990(17) 0.54784(9) 0.0158(3) Uani 1 1 d . . . . .
H1 H 0.601897 0.187470 0.498216 0.019 Uiso 1 1 calc R U . . .
C5 C 0.6333(2) 0.1351(2) 0.76074(11) 0.0173(3) Uani 1 1 d . . . . .
C14 C 0.7511(2) 0.5128(2) 0.48748(10) 0.0156(3) Uani 1 1 d . . . . .
C2 C 0.6774(2) 0.2340(2) 0.68953(10) 0.0156(3) Uani 1 1 d . . . . .
C16 C 0.7089(2) 0.5296(2) 0.34421(11) 0.0193(4) Uani 1 1 d . . . . .
H16 H 0.663949 0.473151 0.290830 0.023 Uiso 1 1 calc R U . . .
C1 C 0.6086(2) 0.1391(2) 0.61051(11) 0.0176(4) Uani 1 1 d . . . . .
C11 C 0.8167(2) 0.6773(2) 0.79411(11) 0.0178(4) Uani 1 1 d . . . . .
H11 H 0.737286 0.715469 0.757212 0.021 Uiso 1 1 calc R U . . .
C13 C 1.0092(3) 0.7215(2) 0.91902(11) 0.0222(4) Uani 1 1 d . . . . .
C17 C 0.8002(2) 0.7109(2) 0.35717(11) 0.0172(3) Uani 1 1 d . . . . .
C18 C 0.8668(3) 0.7919(2) 0.43526(12) 0.0229(4) Uani 1 1 d . . . . .
H18 H 0.929558 0.914685 0.444700 0.028 Uiso 1 1 calc R U . . .
C12 C 0.8915(3) 0.7794(2) 0.86742(11) 0.0206(4) Uani 1 1 d . . . . .
H12 H 0.862484 0.886208 0.881787 0.025 Uiso 1 1 calc R U . . .
C3 C 0.7724(2) 0.4123(2) 0.69548(10) 0.0156(3) Uani 1 1 d . . . . .
C10 C 0.8570(2) 0.5188(2) 0.77396(10) 0.0162(3) Uani 1 1 d . . . . .
C9 C 0.9770(3) 0.4651(2) 0.82777(11) 0.0203(4) Uani 1 1 d . . . . .
H9 H 1.004876 0.357398 0.814376 0.024 Uiso 1 1 calc R U . . .
C15 C 0.6838(2) 0.4328(2) 0.40827(11) 0.0186(4) Uani 1 1 d . . . . .
H15 H 0.620102 0.310197 0.398729 0.022 Uiso 1 1 calc R U . . .
C4 C 0.7293(2) 0.4167(2) 0.55837(10) 0.0147(3) Uani 1 1 d . . . . .
C19 C 0.8418(3) 0.6938(2) 0.49924(11) 0.0225(4) Uani 1 1 d . . . . .
H19 H 0.887244 0.750710 0.552504 0.027 Uiso 1 1 calc R U . . .
C8 C 1.0555(3) 0.5674(2) 0.90034(11) 0.0230(4) Uani 1 1 d . . . . .
H8 H 1.139531 0.532481 0.936594 0.028 Uiso 1 1 calc R U . . .
C6 C 0.4958(3) 0.1271(2) 0.88801(12) 0.0269(4) Uani 1 1 d . . . . .
H6BC H 0.620778 0.132735 0.919238 0.032 Uiso 0.5 1 calc R U P A 2
H6BD H 0.416059 0.002868 0.873844 0.032 Uiso 0.5 1 calc R U P A 2
H6AA H 0.617260 0.107143 0.911820 0.032 Uiso 0.5 1 calc R U P B 1
H6AB H 0.391150 0.012814 0.874972 0.032 Uiso 0.5 1 calc R U P B 1
C20 C 0.8932(3) 0.9826(2) 0.30175(12) 0.0232(4) Uani 1 1 d . . . . .
H20A H 0.889000 1.026572 0.249335 0.035 Uiso 1 1 calc R U . . .
H20B H 1.031655 1.019726 0.325170 0.035 Uiso 1 1 calc R U . . .
H20C H 0.809739 1.029437 0.338506 0.035 Uiso 1 1 calc R U . . .
C0 C 0.382(4) 0.223(3) 0.9349(14) 0.040(2) Uani 0.5 1 d . . P C 2
H0A H 0.458906 0.347112 0.945008 0.061 Uiso 0.5 1 calc R U P C 2
H0B H 0.354303 0.176449 0.986736 0.061 Uiso 0.5 1 calc R U P C 2
H0C H 0.254667 0.209795 0.904548 0.061 Uiso 0.5 1 calc R U P C 2
C7 C 0.420(4) 0.252(3) 0.9493(14) 0.040(2) Uani 0.5 1 d . . P C 1
H7A H 0.520496 0.367798 0.958582 0.061 Uiso 0.5 1 calc R U P C 1
H7B H 0.397110 0.203696 1.000844 0.061 Uiso 0.5 1 calc R U P C 1
H7C H 0.293883 0.263963 0.926800 0.061 Uiso 0.5 1 calc R U P C 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O3 C6 115.68(13) . . ?
C17 O4 C20 117.80(14) . . ?
C4 N2 C3 118.06(14) . . ?
C1 N1 H1 118.2 . . ?
C4 N1 H1 118.2 . . ?
C4 N1 C1 123.64(14) . . ?
O3 C5 C2 111.50(13) . . ?
O2 C5 O3 123.87(16) . . ?
O2 C5 C2 124.60(15) . . ?
C15 C14 C4 123.50(14) . . ?
C19 C14 C15 117.87(16) . . ?
C19 C14 C4 118.63(15) . . ?
C1 C2 C5 117.57(14) . . ?
C3 C2 C5 123.90(15) . . ?
C3 C2 C1 118.46(15) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.40(16) . . ?
O1 C1 N1 119.97(15) . . ?
O1 C1 C2 125.19(16) . . ?
N1 C1 C2 114.82(14) . . ?
C12 C11 H11 119.7 . . ?
C12 C11 C10 120.61(16) . . ?
C10 C11 H11 119.7 . . ?
F001 C13 C12 118.57(15) . . ?
F001 C13 C8 118.69(16) . . ?
C12 C13 C8 122.73(17) . . ?
O4 C17 C16 116.02(15) . . ?
O4 C17 C18 124.62(15) . . ?
C18 C17 C16 119.35(16) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 119.92(16) . . ?
C19 C18 H18 120.0 . . ?
C11 C12 H12 120.9 . . ?
C13 C12 C11 118.20(15) . . ?
C13 C12 H12 120.9 . . ?
N2 C3 C2 123.27(15) . . ?
N2 C3 C10 114.63(13) . . ?
C2 C3 C10 122.10(15) . . ?
C11 C10 C3 119.05(15) . . ?
C9 C10 C11 119.41(16) . . ?
C9 C10 C3 121.54(14) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 C10 120.48(15) . . ?
C8 C9 H9 119.8 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.89(15) . . ?
C16 C15 H15 119.6 . . ?
N2 C4 N1 121.67(15) . . ?
N2 C4 C14 119.05(14) . . ?
N1 C4 C14 119.28(15) . . ?
C14 C19 H19 119.2 . . ?
C18 C19 C14 121.55(17) . . ?
C18 C19 H19 119.2 . . ?
C13 C8 C9 118.55(16) . . ?
C13 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
O3 C6 H6BC 110.6 . . ?
O3 C6 H6BD 110.6 . . ?
O3 C6 H6AA 110.3 . . ?
O3 C6 H6AB 110.3 . . ?
O3 C6 C0 105.8(12) . . ?
O3 C6 C7 107.1(11) . . ?
H6BC C6 H6BD 108.7 . . ?
H6AA C6 H6AB 108.5 . . ?
C0 C6 H6BC 110.6 . . ?
C0 C6 H6BD 110.6 . . ?
C7 C6 H6AA 110.3 . . ?
C7 C6 H6AB 110.3 . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C6 C0 H0A 109.5 . . ?
C6 C0 H0B 109.5 . . ?
C6 C0 H0C 109.5 . . ?
H0A C0 H0B 109.5 . . ?
H0A C0 H0C 109.5 . . ?
H0B C0 H0C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
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
F001 C13 1.359(2) . ?
O3 C5 1.334(2) . ?
O3 C6 1.445(2) . ?
O4 C17 1.354(2) . ?
O4 C20 1.4390(19) . ?
O2 C5 1.209(2) . ?
O1 C1 1.242(2) . ?
N2 C3 1.361(2) . ?
N2 C4 1.318(2) . ?
N1 H1 0.8800 . ?
N1 C1 1.376(2) . ?
N1 C4 1.365(2) . ?
C5 C2 1.491(2) . ?
C14 C15 1.402(2) . ?
C14 C4 1.469(2) . ?
C14 C19 1.398(2) . ?
C2 C1 1.437(2) . ?
C2 C3 1.385(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.400(2) . ?
C16 C15 1.375(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(2) . ?
C11 C10 1.397(2) . ?
C13 C12 1.381(3) . ?
C13 C8 1.381(3) . ?
C17 C18 1.387(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.380(3) . ?
C12 H12 0.9500 . ?
C3 C10 1.481(2) . ?
C10 C9 1.396(2) . ?
C9 H9 0.9500 . ?
C9 C8 1.382(3) . ?
C15 H15 0.9500 . ?
C19 H19 0.9500 . ?
C8 H8 0.9500 . ?
C6 H6BC 0.9900 . ?
C6 H6BD 0.9900 . ?
C6 H6AA 0.9900 . ?
C6 H6AB 0.9900 . ?
C6 C0 1.46(3) . ?
C6 C7 1.57(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C0 H0A 0.9800 . ?
C0 H0B 0.9800 . ?
C0 H0C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F001 C13 C12 C11 179.77(15) . . . . ?
F001 C13 C8 C9 179.01(15) . . . . ?
O3 C5 C2 C1 -126.50(15) . . . . ?
O3 C5 C2 C3 50.6(2) . . . . ?
O4 C17 C18 C19 -179.59(16) . . . . ?
O2 C5 C2 C1 51.8(2) . . . . ?
O2 C5 C2 C3 -131.17(19) . . . . ?
N2 C3 C10 C11 47.4(2) . . . . ?
N2 C3 C10 C9 -132.12(16) . . . . ?
C5 O3 C6 C0 -175.2(7) . . . . ?
C5 O3 C6 C7 171.4(8) . . . . ?
C5 C2 C1 O1 -3.0(2) . . . . ?
C5 C2 C1 N1 175.39(13) . . . . ?
C5 C2 C3 N2 -174.48(14) . . . . ?
C5 C2 C3 C10 6.0(2) . . . . ?
C2 C3 C10 C11 -133.13(17) . . . . ?
C2 C3 C10 C9 47.4(2) . . . . ?
C16 C17 C18 C19 -0.3(3) . . . . ?
C1 N1 C4 N2 2.3(2) . . . . ?
C1 N1 C4 C14 -178.23(13) . . . . ?
C1 C2 C3 N2 2.6(2) . . . . ?
C1 C2 C3 C10 -176.92(13) . . . . ?
C11 C10 C9 C8 0.0(3) . . . . ?
C17 C16 C15 C14 -0.8(3) . . . . ?
C17 C18 C19 C14 0.4(3) . . . . ?
C12 C11 C10 C3 179.27(15) . . . . ?
C12 C11 C10 C9 -1.2(2) . . . . ?
C12 C13 C8 C9 -1.5(3) . . . . ?
C3 N2 C4 N1 -1.7(2) . . . . ?
C3 N2 C4 C14 178.89(13) . . . . ?
C3 C2 C1 O1 179.73(16) . . . . ?
C3 C2 C1 N1 -1.8(2) . . . . ?
C3 C10 C9 C8 179.47(16) . . . . ?
C10 C11 C12 C13 1.1(3) . . . . ?
C10 C9 C8 C13 1.3(3) . . . . ?
C15 C14 C4 N2 -179.99(14) . . . . ?
C15 C14 C4 N1 0.5(2) . . . . ?
C15 C14 C19 C18 -0.6(3) . . . . ?
C15 C16 C17 O4 179.88(14) . . . . ?
C15 C16 C17 C18 0.5(3) . . . . ?
C4 N2 C3 C2 -0.8(2) . . . . ?
C4 N2 C3 C10 178.73(13) . . . . ?
C4 N1 C1 O1 178.06(14) . . . . ?
C4 N1 C1 C2 -0.5(2) . . . . ?
C4 C14 C15 C16 -179.84(14) . . . . ?
C4 C14 C19 C18 -179.97(15) . . . . ?
C19 C14 C15 C16 0.8(2) . . . . ?
C19 C14 C4 N2 -0.7(2) . . . . ?
C19 C14 C4 N1 179.88(14) . . . . ?
C8 C13 C12 C11 0.2(3) . . . . ?
C6 O3 C5 O2 3.1(2) . . . . ?
C6 O3 C5 C2 -178.65(14) . . . . ?
C20 O4 C17 C16 174.00(14) . . . . ?
C20 O4 C17 C18 -6.7(2) . . . . ?
