#------------------------------------------------------------------------------
#$Date: 2025-08-21 04:34:05 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301843 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/74/4517482.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_4517482
loop_
_publ_author_name
'Tan, Jin-Fay'
'Bormann, Carl Thomas'
'Severin, Kay'
'Cramer, Nicolai'
_publ_section_title
;
 Alkynyl Triazenes as Fluoroalkyne Surrogates: Regioselective Access to
 4-Fluoro-2-pyridones by a Rh(III)-Catalyzed C--H Activation--Lossen
 Rearrangement--Wallach Reaction
;
_journal_issue                   6
_journal_name_full               'ACS Catalysis'
_journal_page_first              3790
_journal_page_last               3796
_journal_paper_doi               10.1021/acscatal.0c00499
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C18 H14 F N O'
_chemical_formula_sum            'C18 H14 F N O'
_chemical_formula_weight         279.30
_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   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                109.851(3)
_cell_angle_beta                 92.169(3)
_cell_angle_gamma                112.466(3)
_cell_formula_units_Z            4
_cell_length_a                   10.2367(3)
_cell_length_b                   11.4102(4)
_cell_length_c                   13.7829(5)
_cell_measurement_reflns_used    5853
_cell_measurement_temperature    140.00(11)
_cell_measurement_theta_max      72.6110
_cell_measurement_theta_min      3.4570
_cell_volume                     1373.04(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Mercury 4.1.2 (CCDC, 2019)'
_computing_publication_material  'CIFTab (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -77.00  45.00   1.00    2.00    --  -40.91   0.00 150.00  122
  2  ω   -107.00 -66.00   1.00    2.00    --  -40.91-138.00  51.00   41
  3  ω    -46.00  22.00   1.00    2.00    --  -40.91  38.00  30.00   68
  4  ω     36.00  72.00   1.00    2.00    --   40.91-125.00 -60.00   36
  5  ω     31.00  93.00   1.00    2.00    --   40.91-125.00 150.00   62
  6  ω     58.00  88.00   1.00    8.00    --  105.15 178.00 150.00   30
  7  ω    101.00 178.00   1.00    8.00    --  105.15 111.00-120.00   77
  8  ω     36.00  64.00   1.00    8.00    --  105.15 -61.00 -30.00   28
  9  ω     32.00 133.00   1.00    8.00    --  105.15 -77.00-150.00  101
 10  ω     29.00  91.00   1.00    8.00    --  105.15-111.00  60.00   62
 11  ω     78.00 173.00   1.00    8.00    --  105.15  30.00   0.00   95
 12  ω    135.00 160.00   1.00    8.00    --  105.15 111.00 -90.00   25
 13  ω    140.00 174.00   1.00    8.00    --  105.15  30.00 -60.00   34
 14  ω     85.00 111.00   1.00    8.00    --  105.15  30.00 -60.00   26
 15  ω     87.00 112.00   1.00    8.00    --  105.15-111.00 -30.00   25
 16  ω     29.00  86.00   1.00    8.00    --  105.15 -30.00   0.00   57
 17  ω     30.00 123.00   1.00    8.00    --  105.15 -30.00-180.00   93
 18  ω     60.00 110.00   1.00    8.00    --  105.15-111.00  90.00   50
 19  ω     35.00 120.00   1.00    8.00    --  105.15-131.00-133.00   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_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  0.0235
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9488
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.752
_diffrn_reflns_theta_min         3.474
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.571
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark colourless'
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.579
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.077
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0035(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     492
_refine_ls_number_reflns         5303
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0405
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0727P)²+0.2069P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1177
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4732
_reflns_number_total             5303
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs0c00499_si_002.cif
_cod_data_source_block           jft-1-414
_cod_depositor_comments
;Adding full bibliography for 4517481--4517482.cif.

 Adding full bibliography for 4517481--4517482.cif.
;
_cod_original_cell_volume        1373.04(9)
_cod_database_code               4517482
_shelx_shelxl_version_number     2018/3
_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_min   0.668
_shelx_estimated_absorpt_t_max   0.944
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
F1 F 0.20818(8) 0.09224(9) 0.25051(7) 0.0402(2) Uani 1 1 d . . . . .
O1 O 0.69053(8) 0.42398(9) 0.34943(6) 0.0269(2) Uani 1 1 d . . . . .
N1 N 0.56091(11) 0.36902(11) 0.46966(8) 0.0251(2) Uani 1 1 d . . . . .
H1 H 0.6421(19) 0.4344(19) 0.5208(14) 0.041(4) Uiso 1 1 d . . . . .
C1 C 0.43967(13) 0.30187(13) 0.50104(10) 0.0263(2) Uani 1 1 d . . . . .
C2 C 0.32051(13) 0.20812(14) 0.42692(11) 0.0301(3) Uani 1 1 d . . . . .
H2A H 0.2313(19) 0.1559(18) 0.4438(14) 0.040(4) Uiso 1 1 d . . . . .
C3 C 0.32916(12) 0.18624(13) 0.32104(10) 0.0282(3) Uani 1 1 d . . . . .
C4 C 0.44749(12) 0.25429(12) 0.28646(9) 0.0246(2) Uani 1 1 d . . . . .
C5 C 0.57375(12) 0.35327(12) 0.36702(9) 0.0235(2) Uani 1 1 d . . . . .
C6 C 0.44767(15) 0.34010(14) 0.61753(10) 0.0309(3) Uani 1 1 d . . . . .
H6A H 0.4916(19) 0.441(2) 0.6526(14) 0.042(4) Uiso 1 1 d . . . . .
H6B H 0.3501(19) 0.3075(18) 0.6290(13) 0.038(4) Uiso 1 1 d . . . . .
C7 C 0.53195(13) 0.28326(13) 0.66687(9) 0.0273(3) Uani 1 1 d . . . . .
C8 C 0.63950(14) 0.37018(14) 0.75541(10) 0.0314(3) Uani 1 1 d . . . . .
H8 H 0.6637(17) 0.4680(18) 0.7825(13) 0.034(4) Uiso 1 1 d . . . . .
C9 C 0.71414(14) 0.31865(15) 0.80337(10) 0.0354(3) Uani 1 1 d . . . . .
H9 H 0.792(2) 0.386(2) 0.8654(16) 0.051(5) Uiso 1 1 d . . . . .
C10 C 0.68204(15) 0.17973(16) 0.76253(11) 0.0358(3) Uani 1 1 d . . . . .
H10 H 0.7372(19) 0.1427(19) 0.7950(14) 0.042(4) Uiso 1 1 d . . . . .
C11 C 0.57470(16) 0.09237(15) 0.67429(12) 0.0371(3) Uani 1 1 d . . . . .
H11 H 0.549(2) -0.004(2) 0.6451(16) 0.051(5) Uiso 1 1 d . . . . .
C12 C 0.49977(14) 0.14365(14) 0.62652(10) 0.0328(3) Uani 1 1 d . . . . .
H12 H 0.4262(18) 0.0834(18) 0.5664(14) 0.037(4) Uiso 1 1 d . . . . .
C13 C 0.44949(12) 0.23315(12) 0.17406(9) 0.0250(2) Uani 1 1 d . . . . .
C14 C 0.51248(13) 0.34547(13) 0.14477(9) 0.0275(3) Uani 1 1 d . . . . .
H14 H 0.5607(17) 0.4391(18) 0.2013(13) 0.037(4) Uiso 1 1 d . . . . .
C15 C 0.51191(13) 0.32608(14) 0.03962(10) 0.0316(3) Uani 1 1 d . . . . .
H15 H 0.5592(18) 0.4063(19) 0.0208(14) 0.040(4) Uiso 1 1 d . . . . .
C16 C 0.44944(13) 0.19489(15) -0.03799(10) 0.0337(3) Uani 1 1 d . . . . .
H16 H 0.4508(18) 0.1801(18) -0.1120(14) 0.042(4) Uiso 1 1 d . . . . .
C17 C 0.38699(16) 0.08351(15) -0.01015(11) 0.0403(3) Uani 1 1 d . . . . .
H17 H 0.341(2) -0.009(2) -0.0653(16) 0.056(5) Uiso 1 1 d . . . . .
C18 C 0.38692(15) 0.10226(14) 0.09511(11) 0.0364(3) Uani 1 1 d . . . . .
H18 H 0.3440(19) 0.022(2) 0.1127(14) 0.046(5) Uiso 1 1 d . . . . .
F2 F 1.28676(7) 0.86276(8) 0.72698(6) 0.03268(19) Uani 1 1 d . . . . .
O2 O 0.79261(9) 0.56292(9) 0.62586(7) 0.0297(2) Uani 1 1 d . . . . .
N2 N 0.92591(11) 0.61799(10) 0.50717(8) 0.0240(2) Uani 1 1 d . . . . .
H2 H 0.8477(18) 0.5588(18) 0.4573(13) 0.032(4) Uiso 1 1 d . . . . .
C19 C 1.05004(12) 0.68132(12) 0.47695(9) 0.0240(2) Uani 1 1 d . . . . .
C20 C 1.17263(13) 0.76404(12) 0.55118(9) 0.0262(3) Uani 1 1 d . . . . .
H20 H 1.2627(18) 0.8105(17) 0.5347(13) 0.035(4) Uiso 1 1 d . . . . .
C21 C 1.16357(12) 0.77834(12) 0.65587(9) 0.0253(2) Uani 1 1 d . . . . .
C22 C 1.04143(12) 0.71492(12) 0.68901(9) 0.0237(2) Uani 1 1 d . . . . .
C23 C 0.91180(12) 0.62817(12) 0.60866(9) 0.0239(2) Uani 1 1 d . . . . .
C24 C 1.04150(14) 0.65394(13) 0.36175(9) 0.0273(3) Uani 1 1 d . . . . .
H24A H 0.9938(18) 0.5556(18) 0.3212(13) 0.036(4) Uiso 1 1 d . . . . .
H24B H 1.1400(18) 0.6863(17) 0.3479(13) 0.036(4) Uiso 1 1 d . . . . .
C25 C 0.96411(12) 0.72490(12) 0.32325(9) 0.0247(2) Uani 1 1 d . . . . .
C26 C 1.00098(14) 0.86407(14) 0.37577(11) 0.0346(3) Uani 1 1 d . . . . .
H26 H 1.074(2) 0.9147(19) 0.4377(15) 0.043(4) Uiso 1 1 d . . . . .
C27 C 0.93456(15) 0.92983(14) 0.33780(12) 0.0384(3) Uani 1 1 d . . . . .
H27 H 0.965(2) 1.029(2) 0.3761(17) 0.062(6) Uiso 1 1 d . . . . .
C28 C 0.83012(14) 0.85725(15) 0.24704(11) 0.0335(3) Uani 1 1 d . . . . .
H28 H 0.7841(18) 0.9046(18) 0.2200(14) 0.040(4) Uiso 1 1 d . . . . .
C29 C 0.79181(14) 0.71873(15) 0.19474(10) 0.0338(3) Uani 1 1 d . . . . .
H29 H 0.720(2) 0.6707(19) 0.1321(15) 0.045(5) Uiso 1 1 d . . . . .
C30 C 0.85901(14) 0.65289(13) 0.23255(9) 0.0304(3) Uani 1 1 d . . . . .
H30 H 0.8311(19) 0.5540(19) 0.1970(14) 0.042(4) Uiso 1 1 d . . . . .
C31 C 1.03838(12) 0.72542(12) 0.79920(9) 0.0253(2) Uani 1 1 d . . . . .
C32 C 0.92916(15) 0.74765(16) 0.84899(11) 0.0362(3) Uani 1 1 d . . . . .
H32 H 0.8537(18) 0.7578(18) 0.8111(14) 0.040(4) Uiso 1 1 d . . . . .
C33 C 0.92691(16) 0.75658(18) 0.95186(11) 0.0445(4) Uani 1 1 d . . . . .
H33 H 0.847(2) 0.773(2) 0.9835(15) 0.053(5) Uiso 1 1 d . . . . .
C34 C 1.03288(16) 0.74218(17) 1.00575(10) 0.0411(3) Uani 1 1 d . . . . .
H34 H 1.030(2) 0.748(2) 1.0786(16) 0.053(5) Uiso 1 1 d . . . . .
C35 C 1.14104(14) 0.71875(15) 0.95654(10) 0.0343(3) Uani 1 1 d . . . . .
H35 H 1.2145(19) 0.7068(18) 0.9912(14) 0.041(4) Uiso 1 1 d . . . . .
C36 C 1.14445(13) 0.71062(12) 0.85396(9) 0.0273(3) Uani 1 1 d . . . . .
H36 H 1.2205(17) 0.6925(16) 0.8216(12) 0.032(4) 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 0.0181 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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 -1 0.0533
-2 1 0 0.3168
0 2 -9 0.0369
1 -1 8 0.0349
-1 0 8 0.0342
0 -7 6 0.0636
0 -4 -5 0.0423
0 4 5 0.0361
7 -3 -1 0.2609
0 7 -2 0.0396
0 5 3 0.0307
1 -3 -7 0.0508
0 -7 3 0.0533
3 -7 2 0.1031
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
C1 N1 C5 125.56(11) . . ?
C2 C1 N1 118.81(11) . . ?
C2 C1 C6 124.57(11) . . ?
N1 C1 C6 116.61(11) . . ?
C1 C2 C3 117.75(11) . . ?
F1 C3 C4 119.25(11) . . ?
F1 C3 C2 115.49(10) . . ?
C4 C3 C2 125.24(11) . . ?
C3 C4 C5 115.98(11) . . ?
C3 C4 C13 123.46(11) . . ?
C5 C4 C13 120.55(10) . . ?
O1 C5 N1 118.95(10) . . ?
O1 C5 C4 124.43(10) . . ?
N1 C5 C4 116.61(10) . . ?
C1 C6 C7 114.68(9) . . ?
C8 C7 C12 119.11(11) . . ?
C8 C7 C6 119.97(12) . . ?
C12 C7 C6 120.88(12) . . ?
C7 C8 C9 120.52(13) . . ?
C10 C9 C8 120.07(13) . . ?
C11 C10 C9 119.72(12) . . ?
C10 C11 C12 120.26(13) . . ?
C11 C12 C7 120.31(13) . . ?
C18 C13 C14 118.19(11) . . ?
C18 C13 C4 121.26(11) . . ?
C14 C13 C4 120.54(11) . . ?
C15 C14 C13 120.62(11) . . ?
C16 C15 C14 120.43(12) . . ?
C17 C16 C15 119.50(12) . . ?
C16 C17 C18 120.37(12) . . ?
C13 C18 C17 120.90(13) . . ?
C19 N2 C23 125.62(10) . . ?
N2 C19 C20 119.00(10) . . ?
N2 C19 C24 116.75(10) . . ?
C20 C19 C24 124.25(11) . . ?
C19 C20 C21 117.52(11) . . ?
F2 C21 C22 119.26(10) . . ?
F2 C21 C20 115.58(10) . . ?
C22 C21 C20 125.16(11) . . ?
C21 C22 C23 116.35(10) . . ?
C21 C22 C31 123.51(11) . . ?
C23 C22 C31 120.05(10) . . ?
O2 C23 N2 119.45(10) . . ?
O2 C23 C22 124.20(10) . . ?
N2 C23 C22 116.34(10) . . ?
C19 C24 C25 113.79(9) . . ?
C30 C25 C26 118.59(11) . . ?
C30 C25 C24 120.54(11) . . ?
C26 C25 C24 120.83(11) . . ?
C25 C26 C27 120.68(12) . . ?
C28 C27 C26 120.33(13) . . ?
C29 C28 C27 119.46(12) . . ?
C28 C29 C30 120.20(12) . . ?
C25 C30 C29 120.73(12) . . ?
C36 C31 C32 118.89(11) . . ?
C36 C31 C22 120.02(10) . . ?
C32 C31 C22 121.07(11) . . ?
C33 C32 C31 120.60(12) . . ?
C34 C33 C32 120.12(12) . . ?
C33 C34 C35 119.67(12) . . ?
C34 C35 C36 120.51(12) . . ?
C35 C36 C31 120.21(11) . . ?
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
F1 C3 1.3471(14) . ?
O1 C5 1.2475(15) . ?
N1 C1 1.3614(15) . ?
N1 C5 1.3821(14) . ?
C1 C2 1.3573(19) . ?
C1 C6 1.5040(16) . ?
C2 C3 1.4068(18) . ?
C3 C4 1.3688(17) . ?
C4 C5 1.4502(16) . ?
C4 C13 1.4870(16) . ?
C6 C7 1.5198(17) . ?
C7 C8 1.3881(19) . ?
C7 C12 1.3924(18) . ?
C8 C9 1.3912(19) . ?
C9 C10 1.385(2) . ?
C10 C11 1.385(2) . ?
C11 C12 1.3895(19) . ?
C13 C18 1.3919(18) . ?
C13 C14 1.4003(17) . ?
C14 C15 1.3892(17) . ?
C15 C16 1.3867(19) . ?
C16 C17 1.378(2) . ?
C17 C18 1.3929(19) . ?
F2 C21 1.3474(14) . ?
O2 C23 1.2436(15) . ?
N2 C19 1.3613(15) . ?
N2 C23 1.3816(15) . ?
C19 C20 1.3617(17) . ?
C19 C24 1.5027(15) . ?
C20 C21 1.4067(16) . ?
C21 C22 1.3682(17) . ?
C22 C23 1.4518(16) . ?
C22 C31 1.4849(15) . ?
C24 C25 1.5214(16) . ?
C25 C30 1.3858(18) . ?
C25 C26 1.3888(18) . ?
C26 C27 1.3889(19) . ?
C27 C28 1.383(2) . ?
C28 C29 1.379(2) . ?
C29 C30 1.3937(19) . ?
C31 C36 1.3935(17) . ?
C31 C32 1.3935(17) . ?
C32 C33 1.3884(19) . ?
C33 C34 1.383(2) . ?
C34 C35 1.3847(19) . ?
C35 C36 1.3878(17) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O2 0.933(19) 1.811(19) 2.7429(13) 176.5(16) . yes
N2 H2 O1 0.894(18) 1.882(18) 2.7733(13) 175.1(15) . yes
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
C5 N1 C1 C2 1.87(17) . . . . ?
C5 N1 C1 C6 -177.01(10) . . . . ?
N1 C1 C2 C3 -0.36(17) . . . . ?
C6 C1 C2 C3 178.42(11) . . . . ?
C1 C2 C3 F1 179.98(10) . . . . ?
C1 C2 C3 C4 -1.57(19) . . . . ?
F1 C3 C4 C5 -179.66(10) . . . . ?
C2 C3 C4 C5 1.95(18) . . . . ?
F1 C3 C4 C13 1.73(17) . . . . ?
C2 C3 C4 C13 -176.66(11) . . . . ?
C1 N1 C5 O1 178.23(10) . . . . ?
C1 N1 C5 C4 -1.42(16) . . . . ?
C3 C4 C5 O1 179.90(11) . . . . ?
C13 C4 C5 O1 -1.44(17) . . . . ?
C3 C4 C5 N1 -0.46(15) . . . . ?
C13 C4 C5 N1 178.19(10) . . . . ?
C2 C1 C6 C7 106.08(14) . . . . ?
N1 C1 C6 C7 -75.12(14) . . . . ?
C1 C6 C7 C8 129.27(12) . . . . ?
C1 C6 C7 C12 -52.86(16) . . . . ?
C12 C7 C8 C9 -0.06(17) . . . . ?
C6 C7 C8 C9 177.85(11) . . . . ?
C7 C8 C9 C10 0.36(18) . . . . ?
C8 C9 C10 C11 -0.46(19) . . . . ?
C9 C10 C11 C12 0.3(2) . . . . ?
C10 C11 C12 C7 0.0(2) . . . . ?
C8 C7 C12 C11 -0.14(18) . . . . ?
C6 C7 C12 C11 -178.03(11) . . . . ?
C3 C4 C13 C18 -42.78(17) . . . . ?
C5 C4 C13 C18 138.67(12) . . . . ?
C3 C4 C13 C14 136.02(12) . . . . ?
C5 C4 C13 C14 -42.53(15) . . . . ?
C18 C13 C14 C15 0.12(17) . . . . ?
C4 C13 C14 C15 -178.72(11) . . . . ?
C13 C14 C15 C16 -0.31(18) . . . . ?
C14 C15 C16 C17 0.36(19) . . . . ?
C15 C16 C17 C18 -0.2(2) . . . . ?
C14 C13 C18 C17 0.01(19) . . . . ?
C4 C13 C18 C17 178.84(12) . . . . ?
C16 C17 C18 C13 0.0(2) . . . . ?
C23 N2 C19 C20 -0.91(17) . . . . ?
C23 N2 C19 C24 178.95(10) . . . . ?
N2 C19 C20 C21 0.47(16) . . . . ?
C24 C19 C20 C21 -179.38(10) . . . . ?
C19 C20 C21 F2 -179.00(10) . . . . ?
C19 C20 C21 C22 0.48(18) . . . . ?
F2 C21 C22 C23 178.48(9) . . . . ?
C20 C21 C22 C23 -0.98(17) . . . . ?
F2 C21 C22 C31 -4.71(17) . . . . ?
C20 C21 C22 C31 175.84(10) . . . . ?
C19 N2 C23 O2 -178.64(10) . . . . ?
C19 N2 C23 C22 0.38(16) . . . . ?
C21 C22 C23 O2 179.50(11) . . . . ?
C31 C22 C23 O2 2.58(17) . . . . ?
C21 C22 C23 N2 0.54(15) . . . . ?
C31 C22 C23 N2 -176.39(9) . . . . ?
N2 C19 C24 C25 73.06(13) . . . . ?
C20 C19 C24 C25 -107.09(13) . . . . ?
C19 C24 C25 C30 -132.49(11) . . . . ?
C19 C24 C25 C26 50.01(15) . . . . ?
C30 C25 C26 C27 -0.41(19) . . . . ?
C24 C25 C26 C27 177.14(12) . . . . ?
C25 C26 C27 C28 0.2(2) . . . . ?
C26 C27 C28 C29 0.3(2) . . . . ?
C27 C28 C29 C30 -0.7(2) . . . . ?
C26 C25 C30 C29 0.07(18) . . . . ?
C24 C25 C30 C29 -177.48(11) . . . . ?
C28 C29 C30 C25 0.47(19) . . . . ?
C21 C22 C31 C36 -45.23(17) . . . . ?
C23 C22 C31 C36 131.47(12) . . . . ?
C21 C22 C31 C32 135.89(13) . . . . ?
C23 C22 C31 C32 -47.41(16) . . . . ?
C36 C31 C32 C33 0.8(2) . . . . ?
C22 C31 C32 C33 179.66(13) . . . . ?
C31 C32 C33 C34 -0.6(2) . . . . ?
C32 C33 C34 C35 0.0(3) . . . . ?
C33 C34 C35 C36 0.5(2) . . . . ?
C34 C35 C36 C31 -0.3(2) . . . . ?
C32 C31 C36 C35 -0.34(19) . . . . ?
C22 C31 C36 C35 -179.24(11) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168346583
