#------------------------------------------------------------------------------
#$Date: 2024-07-05 19:57:33 +0200 (Fri 05 de Jul de 2024) $
#$Revision: 293259 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/99/7159934.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_7159934
loop_
_publ_author_name
'Chang, Meng-Yang'
'Ho, Chin-Huey'
'Chen, Hsing-Yin'
_publ_section_title
;
 K₂CO₃-mediated annulation of
 1,3-acetonedicarboxylates with 2-fluoro-1-nitroarenes: synthesis of
 indoles.
;
_journal_issue                   20
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4108
_journal_page_last               4122
_journal_paper_doi               10.1039/d4ob00488d
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C18 H12 F2 N2 O6'
_chemical_formula_sum            'C18 H12 F2 N2 O6'
_chemical_formula_weight         390.30
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-26
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-12-04 deposited with the CCDC.	2024-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                68.919(2)
_cell_angle_beta                 77.025(2)
_cell_angle_gamma                82.949(2)
_cell_formula_units_Z            2
_cell_length_a                   7.8953(2)
_cell_length_b                   10.6880(2)
_cell_length_c                   10.9838(2)
_cell_measurement_reflns_used    13449
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      26.8400
_cell_measurement_theta_min      2.0220
_cell_volume                     841.85(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      130(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00  41.00   0.50    1.28    --   10.60 -57.00   0.00  240
  2  ω    -17.00 100.00   0.50    1.28    --   10.60  82.00-120.00  234
  3  ω    -17.00 100.00   0.50    1.28    --   10.60  82.00   0.00  234
  4  ω    -79.00  36.00   0.50    1.28    --   10.60 -62.00 148.83  230
  5  ω    -79.00  36.00   0.50    1.28    --   10.60 -77.00  90.00  230
  6  ω    -17.00 100.00   0.50    1.28    --   10.60  82.00 -60.00  234
  7  ω    -17.00 100.00   0.50    1.28    --   10.60  82.00  90.00  234
  8  ω    -20.00 100.00   0.50    1.28    --   10.60  57.00-120.00  240
  9  ω    -17.00 100.00   0.50    1.28    --   10.60  82.00 150.00  234
 10  ω    -79.00  38.00   0.50    1.28    --   10.60 -82.00 -90.00  234
 11  ω    -79.00  38.00   0.50    1.28    --   10.60 -82.00-150.00  234
 12  ω    -79.00  38.00   0.50    1.28    --   10.60 -82.00 150.00  234
 13  ω    -79.00  38.00   0.50    1.28    --   10.60 -82.00 -30.00  234
 14  ω    -38.00 -10.00   0.50    1.28    --  -10.90  82.00   0.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0001171000
_diffrn_orient_matrix_UB_12      -0.0591781000
_diffrn_orient_matrix_UB_13      0.0565478000
_diffrn_orient_matrix_UB_21      -0.0271483000
_diffrn_orient_matrix_UB_22      0.0386918000
_diffrn_orient_matrix_UB_23      0.0421823000
_diffrn_orient_matrix_UB_31      -0.0882067000
_diffrn_orient_matrix_UB_32      -0.0083892000
_diffrn_orient_matrix_UB_33      0.0013218000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            22714
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.971
_diffrn_reflns_theta_min         2.026
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50166
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.012(3)
_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   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3516
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0389
_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)+(0.0474P)²+0.3899P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1035
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3065
_reflns_number_total             3516
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00488d3.cif
_cod_data_source_block           k11204-myc-f_auto
_cod_depositor_comments
'Adding full bibliography for 7159934--7159937.cif.'
_cod_original_cell_volume        841.86(3)
_cod_database_code               7159934
_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_max   0.949
_shelx_estimated_absorpt_t_min   0.937
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C3(H3), C17(H17), C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C9(H9A,H9B,H9C)
;
_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 1.770
_oxdiff_exptl_absorpt_empirical_full_min 0.623
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 0.55304(13) 0.64053(9) 1.08092(9) 0.0304(2) Uani 1 1 d . . . . .
F2 F 0.65656(12) 0.92208(9) 0.48345(9) 0.0300(2) Uani 1 1 d . . . . .
O2 O 0.07252(14) 0.72630(10) 1.02441(10) 0.0251(3) Uani 1 1 d . . . . .
O4 O 0.04635(14) 0.91274(10) 0.76359(10) 0.0235(3) Uani 1 1 d . . . . .
O3 O 0.09302(14) 0.82701(11) 0.59846(10) 0.0254(3) Uani 1 1 d . . . . .
O1 O 0.26277(15) 0.86907(12) 1.01864(12) 0.0334(3) Uani 1 1 d . . . . .
O5 O 0.28783(18) 0.51729(12) 0.67143(14) 0.0425(3) Uani 1 1 d . . . . .
N1 N 0.43672(16) 0.73604(12) 0.66320(12) 0.0192(3) Uani 1 1 d . . . . .
O6 O 0.14196(19) 0.55961(16) 0.51483(15) 0.0522(4) Uani 1 1 d . . . . .
N2 N 0.26101(19) 0.58108(14) 0.55921(15) 0.0317(3) Uani 1 1 d . . . . .
C7 C 0.33164(18) 0.75132(13) 0.86608(14) 0.0179(3) Uani 1 1 d . . . . .
C10 C 0.29444(18) 0.77707(13) 0.74290(14) 0.0179(3) Uani 1 1 d . . . . .
C11 C 0.13555(19) 0.84015(14) 0.69156(14) 0.0184(3) Uani 1 1 d . . . . .
C8 C 0.22121(19) 0.78947(14) 0.97726(14) 0.0202(3) Uani 1 1 d . . . . .
C6 C 0.50406(19) 0.69165(14) 0.86359(14) 0.0184(3) Uani 1 1 d . . . . .
C1 C 0.56655(19) 0.68316(14) 0.73619(14) 0.0192(3) Uani 1 1 d . . . . .
C5 C 0.6131(2) 0.63866(14) 0.95603(14) 0.0214(3) Uani 1 1 d . . . . .
C2 C 0.7315(2) 0.62809(15) 0.69896(15) 0.0244(3) Uani 1 1 d . . . . .
H2 H 0.771543 0.624357 0.612003 0.029 Uiso 1 1 calc R U . . .
C13 C 0.4599(2) 0.75768(15) 0.52522(14) 0.0219(3) Uani 1 1 d . . . . .
C4 C 0.7745(2) 0.58396(15) 0.92388(16) 0.0257(3) Uani 1 1 d . . . . .
H4 H 0.846981 0.549150 0.988019 0.031 Uiso 1 1 calc R U . . .
C14 C 0.3752(2) 0.68971(16) 0.47098(16) 0.0249(3) Uani 1 1 d . . . . .
C18 C 0.5708(2) 0.85629(15) 0.43398(15) 0.0232(3) Uani 1 1 d . . . . .
C3 C 0.8328(2) 0.57960(15) 0.79437(16) 0.0271(4) Uani 1 1 d . . . . .
H3 H 0.945827 0.541908 0.772254 0.032 Uiso 1 1 calc R U . . .
C17 C 0.5939(2) 0.88860(16) 0.29899(16) 0.0288(4) Uani 1 1 d . . . . .
H17 H 0.670525 0.956411 0.240403 0.035 Uiso 1 1 calc R U . . .
C15 C 0.3953(2) 0.72095(17) 0.33491(16) 0.0277(4) Uani 1 1 d . . . . .
H15 H 0.334620 0.673719 0.300702 0.033 Uiso 1 1 calc R U . . .
C16 C 0.5037(2) 0.82071(17) 0.24950(16) 0.0298(4) Uani 1 1 d . . . . .
H16 H 0.516665 0.843077 0.156102 0.036 Uiso 1 1 calc R U . . .
C12 C -0.1210(2) 0.97037(18) 0.73038(17) 0.0307(4) Uani 1 1 d . . . . .
H12A H -0.102929 1.036432 0.640051 0.046 Uiso 1 1 calc R U . . .
H12B H -0.180913 1.014470 0.793539 0.046 Uiso 1 1 calc R U . . .
H12C H -0.191945 0.899061 0.735145 0.046 Uiso 1 1 calc R U . . .
C9 C -0.0485(2) 0.76768(18) 1.12455(18) 0.0361(4) Uani 1 1 d . . . . .
H9A H -0.079880 0.863547 1.087252 0.054 Uiso 1 1 calc R U . . .
H9B H 0.005834 0.751430 1.201122 0.054 Uiso 1 1 calc R U . . .
H9C H -0.153484 0.716080 1.153105 0.054 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C8 O2 C9 115.28(12) . . ?
C11 O4 C12 115.56(11) . . ?
C10 N1 C13 127.44(12) . . ?
C1 N1 C10 108.69(11) . . ?
C1 N1 C13 123.44(12) . . ?
O5 N2 O6 123.64(15) . . ?
O5 N2 C14 119.41(14) . . ?
O6 N2 C14 116.96(15) . . ?
C10 C7 C8 126.77(13) . . ?
C10 C7 C6 107.00(12) . . ?
C6 C7 C8 126.01(13) . . ?
N1 C10 C11 121.38(12) . . ?
C7 C10 N1 109.30(12) . . ?
C7 C10 C11 129.31(13) . . ?
O4 C11 C10 110.29(12) . . ?
O3 C11 O4 125.17(14) . . ?
O3 C11 C10 124.55(13) . . ?
O2 C8 C7 112.27(12) . . ?
O1 C8 O2 124.46(13) . . ?
O1 C8 C7 123.27(14) . . ?
C1 C6 C7 107.51(12) . . ?
C5 C6 C7 135.35(13) . . ?
C5 C6 C1 117.08(13) . . ?
N1 C1 C6 107.50(12) . . ?
N1 C1 C2 129.44(13) . . ?
C2 C1 C6 123.05(14) . . ?
F1 C5 C6 118.20(13) . . ?
F1 C5 C4 120.08(13) . . ?
C4 C5 C6 121.71(14) . . ?
C1 C2 H2 121.6 . . ?
C3 C2 C1 116.73(14) . . ?
C3 C2 H2 121.6 . . ?
C14 C13 N1 124.73(14) . . ?
C14 C13 C18 115.87(14) . . ?
C18 C13 N1 119.37(13) . . ?
C5 C4 H4 120.4 . . ?
C5 C4 C3 119.24(14) . . ?
C3 C4 H4 120.4 . . ?
C13 C14 N2 119.77(14) . . ?
C15 C14 N2 118.22(14) . . ?
C15 C14 C13 122.01(15) . . ?
F2 C18 C13 117.24(13) . . ?
F2 C18 C17 119.48(14) . . ?
C17 C18 C13 123.28(14) . . ?
C2 C3 C4 122.17(14) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C18 C17 H17 120.6 . . ?
C18 C17 C16 118.82(15) . . ?
C16 C17 H17 120.6 . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.68(15) . . ?
C16 C15 H15 120.2 . . ?
C17 C16 H16 119.8 . . ?
C15 C16 C17 120.31(15) . . ?
C15 C16 H16 119.8 . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
F1 C5 1.3537(17) . ?
F2 C18 1.3434(17) . ?
O2 C8 1.3313(18) . ?
O2 C9 1.4467(18) . ?
O4 C11 1.3345(17) . ?
O4 C12 1.4537(18) . ?
O3 C11 1.2031(17) . ?
O1 C8 1.2048(18) . ?
O5 N2 1.227(2) . ?
N1 C10 1.3907(18) . ?
N1 C1 1.3834(19) . ?
N1 C13 1.4204(18) . ?
O6 N2 1.2300(19) . ?
N2 C14 1.468(2) . ?
C7 C10 1.3724(19) . ?
C7 C8 1.4868(19) . ?
C7 C6 1.429(2) . ?
C10 C11 1.477(2) . ?
C6 C1 1.4072(19) . ?
C6 C5 1.397(2) . ?
C1 C2 1.398(2) . ?
C5 C4 1.362(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.375(2) . ?
C13 C14 1.392(2) . ?
C13 C18 1.398(2) . ?
C4 H4 0.9500 . ?
C4 C3 1.409(2) . ?
C14 C15 1.385(2) . ?
C18 C17 1.370(2) . ?
C3 H3 0.9500 . ?
C17 H17 0.9500 . ?
C17 C16 1.383(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.376(2) . ?
C16 H16 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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
F1 C5 C4 C3 178.26(13) . . . . ?
F2 C18 C17 C16 -179.50(14) . . . . ?
O5 N2 C14 C13 -27.2(2) . . . . ?
O5 N2 C14 C15 152.64(15) . . . . ?
N1 C10 C11 O4 -157.69(12) . . . . ?
N1 C10 C11 O3 22.6(2) . . . . ?
N1 C1 C2 C3 -178.38(14) . . . . ?
N1 C13 C14 N2 -4.1(2) . . . . ?
N1 C13 C14 C15 176.04(14) . . . . ?
N1 C13 C18 F2 2.9(2) . . . . ?
N1 C13 C18 C17 -176.55(14) . . . . ?
O6 N2 C14 C13 152.75(15) . . . . ?
O6 N2 C14 C15 -27.4(2) . . . . ?
N2 C14 C15 C16 -178.91(14) . . . . ?
C7 C10 C11 O4 20.9(2) . . . . ?
C7 C10 C11 O3 -158.76(15) . . . . ?
C7 C6 C1 N1 0.07(16) . . . . ?
C7 C6 C1 C2 -179.24(13) . . . . ?
C7 C6 C5 F1 -0.6(2) . . . . ?
C7 C6 C5 C4 178.24(16) . . . . ?
C10 N1 C1 C6 -0.10(15) . . . . ?
C10 N1 C1 C2 179.15(15) . . . . ?
C10 N1 C13 C14 -74.3(2) . . . . ?
C10 N1 C13 C18 103.71(18) . . . . ?
C10 C7 C8 O2 65.58(18) . . . . ?
C10 C7 C8 O1 -114.12(18) . . . . ?
C10 C7 C6 C1 -0.01(16) . . . . ?
C10 C7 C6 C5 -176.93(16) . . . . ?
C8 C7 C10 N1 174.71(13) . . . . ?
C8 C7 C10 C11 -4.0(2) . . . . ?
C8 C7 C6 C1 -174.83(13) . . . . ?
C8 C7 C6 C5 8.2(3) . . . . ?
C6 C7 C10 N1 -0.06(15) . . . . ?
C6 C7 C10 C11 -178.79(13) . . . . ?
C6 C7 C8 O2 -120.60(15) . . . . ?
C6 C7 C8 O1 59.7(2) . . . . ?
C6 C1 C2 C3 0.8(2) . . . . ?
C6 C5 C4 C3 -0.5(2) . . . . ?
C1 N1 C10 C7 0.10(16) . . . . ?
C1 N1 C10 C11 178.95(12) . . . . ?
C1 N1 C13 C14 114.05(17) . . . . ?
C1 N1 C13 C18 -67.94(19) . . . . ?
C1 C6 C5 F1 -177.29(12) . . . . ?
C1 C6 C5 C4 1.5(2) . . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
C5 C6 C1 N1 177.64(12) . . . . ?
C5 C6 C1 C2 -1.7(2) . . . . ?
C5 C4 C3 C2 -0.4(2) . . . . ?
C13 N1 C10 C7 -172.55(13) . . . . ?
C13 N1 C10 C11 6.3(2) . . . . ?
C13 N1 C1 C6 172.90(12) . . . . ?
C13 N1 C1 C2 -7.8(2) . . . . ?
C13 C14 C15 C16 0.9(2) . . . . ?
C13 C18 C17 C16 -0.1(2) . . . . ?
C14 C13 C18 F2 -178.94(13) . . . . ?
C14 C13 C18 C17 1.6(2) . . . . ?
C14 C15 C16 C17 0.8(2) . . . . ?
C18 C13 C14 N2 177.78(13) . . . . ?
C18 C13 C14 C15 -2.0(2) . . . . ?
C18 C17 C16 C15 -1.2(2) . . . . ?
C12 O4 C11 O3 4.9(2) . . . . ?
C12 O4 C11 C10 -174.73(12) . . . . ?
C9 O2 C8 O1 5.1(2) . . . . ?
C9 O2 C8 C7 -174.56(13) . . . . ?
