#------------------------------------------------------------------------------
#$Date: 2022-11-07 06:26:12 +0100 (Mon 07 de Nov de 2022) $
#$Revision: 278988 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/55/7245546.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_7245546
loop_
_publ_author_name
'Yi, Yaping'
'Fan, Zhengning'
'Xi, Chanjuan'
_publ_section_title
;
 Photoredox-catalyzed intermolecular dearomative
 trifluoromethylcarboxylation of indoles and heteroanalogues with CO2 and
 fluorinated radical precursors
;
_journal_issue                   20
_journal_name_full               'Green Chemistry'
_journal_page_first              7894
_journal_page_last               7899
_journal_paper_doi               10.1039/D2GC03000D
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C16 H17 Cl F3 N O4'
_chemical_formula_sum            'C16 H17 Cl F3 N O4'
_chemical_formula_weight         379.76
_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             2022-04-25
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-07-13 deposited with the CCDC.	2022-09-22 downloaded from the CCDC.
;
_cell_angle_alpha                114.406(3)
_cell_angle_beta                 94.673(2)
_cell_angle_gamma                99.133(2)
_cell_formula_units_Z            2
_cell_length_a                   9.1441(2)
_cell_length_b                   10.1797(3)
_cell_length_c                   10.2607(3)
_cell_measurement_reflns_used    7836
_cell_measurement_temperature    170.00(11)
_cell_measurement_theta_max      75.9770
_cell_measurement_theta_min      4.8030
_cell_volume                     847.17(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (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 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     87.00 156.00   0.50    0.05    --  107.36  77.00   0.00  138
  2  ω     65.00 117.00   0.50    0.05    --   47.45 147.00 102.00  104
  3  ω    104.00 131.00   0.50    0.05    --  107.36 124.00 -62.00   54
  4  ω    148.00 175.00   0.50    0.05    --  107.36  38.00-150.00   54
  5  ω    109.00 135.00   0.50    0.05    --  107.36  38.00-150.00   52
  6  ω     71.00 106.00   0.50    0.05    --  107.36 -99.00-180.00   70
  7  ω     48.00  73.00   0.50    0.05    --  107.36-124.00-141.00   50
  8  ω     56.00  81.00   0.50    0.05    --   47.45-124.00-141.00   50
  9  ω     47.00  73.00   0.50    0.05    --   47.45-147.00  53.00   52
 10  ω     36.00 121.00   0.50    0.05    --  107.36-147.00  53.00  170
 11  ω     37.00  65.00   0.50    0.05    --  107.36 -99.00  90.00   56
 12  ω     73.00 104.00   0.50    0.05    --  107.36 -99.00  90.00   62
 13  ω     67.00  94.00   0.50    0.05    --  107.36 -99.00  60.00   54
 14  ω     37.00  64.00   0.50    0.05    --  107.36 -99.00  60.00   54
 15  ω     36.00  95.00   0.50    0.05    --  107.36 -99.00  30.00  118
 16  ω     36.00  99.00   0.50    0.05    --  107.36 -99.00-150.00  126
 17  ω     79.00 105.00   0.50    0.05    --  107.36 -77.00-150.00   52
 18  ω     46.00  71.00   0.50    0.05    --  107.36 -77.00-150.00   50
 19  ω     41.00  68.00   0.50    0.05    --  107.36 -57.00  90.00   54
 20  ω     38.00  67.00   0.50    0.05    --  107.36 -57.00  60.00   58
 21  ω    -21.00  20.00   0.50    0.05    --  -47.45  19.00 120.00   82
 22  ω    -99.00 -65.00   0.50    0.05    --  -47.45 147.00 102.00   68
 23  ω   -127.00 -38.00   0.50    0.05    -- -104.50 147.00 102.00  178
 24  ω    -91.00 -47.00   0.50    0.05    --  -47.45 124.00 -62.00   88
 25  ω   -126.00 -72.00   0.50    0.05    -- -104.50 145.00-141.61  108
 26  ω    -90.00 -64.00   0.50    0.05    -- -104.50 124.00 -62.00   52
 27  ω    -21.00  23.00   0.50    0.05    --  -47.45  19.00 -30.00   88
 28  ω    -22.00  26.00   0.50    0.05    --  -47.45  19.00-150.00   96
 29  ω    -81.00 -55.00   0.50    0.05    -- -104.50  77.00-180.00   52
 30  ω    -62.00 -37.00   0.50    0.05    -- -104.50  57.00 -90.00   50
 31  ω    -62.00 -34.00   0.50    0.05    -- -104.50  57.00 -60.00   56
 32  ω    -58.00 -33.00   0.50    0.05    -- -104.50  57.00 150.00   50
 33  ω   -117.00 -25.00   0.50    0.05    --  -47.45 -77.00-120.00  184
 34  ω   -120.00 -94.00   0.50    0.05    -- -104.50 -19.00-150.00   52
 35  ω   -171.00-136.00   0.50    0.05    -- -104.50 -19.00-150.00   70
 36  ω   -173.00-124.00   0.50    0.05    -- -104.50 -65.00 -65.60   98
 37  ω   -122.00 -95.00   0.50    0.05    -- -104.50 -65.00 -65.60   54
 38  ω   -174.00 -89.00   0.50    0.05    -- -104.50 -61.00 -37.15  170
 39  ω   -137.00-112.00   0.50    0.05    -- -104.50-147.00  53.00   50
 40  ω   -105.00 -78.00   0.50    0.05    --  -47.45-125.00  60.00   54
 41  ω   -118.00 -59.00   0.50    0.05    --  -47.45-147.00  53.00  118
 42  ω   -145.00 -88.00   0.50    0.05    -- -104.50-124.00-141.00  114
 43  ω   -173.00 -86.00   0.50    0.05    -- -104.50 -99.00-180.00  174
 44  ω   -100.00 -74.00   0.50    0.05    --  -47.45-125.00-150.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1591792000
_diffrn_orient_matrix_UB_12      -0.0284964000
_diffrn_orient_matrix_UB_13      0.0353563000
_diffrn_orient_matrix_UB_21      0.0652241000
_diffrn_orient_matrix_UB_22      0.0684238000
_diffrn_orient_matrix_UB_23      0.1627212000
_diffrn_orient_matrix_UB_31      -0.0180583000
_diffrn_orient_matrix_UB_32      0.1530483000
_diffrn_orient_matrix_UB_33      0.0142491000
_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  0.0216
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9766
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.347
_diffrn_reflns_theta_min         4.797
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.496
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86219
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
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    1.489
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0022(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3386
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0334
_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)+(0.0523P)²+0.2174P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0934
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3147
_reflns_number_total             3386
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2gc03000d2.cif
_cod_data_source_block           tx10770
_cod_depositor_comments          'Adding full bibliography for 7245546.cif.'
_cod_original_cell_volume        847.16(4)
_cod_database_code               7245546
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H N O F Cl'
_chemical_oxdiff_usercomment     ' '
_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.
;
_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 Ternary CH refined with riding coordinates:
 C2(H2), C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H3), C5(H4), C6(H5)
2.c Idealised Me refined as rotating group:
 C14(H12,H13,H14), C10(H6,H8,H7), C13(H9,H11,H10), C15(H16,H15,H17)
;
_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 1.387
_oxdiff_exptl_absorpt_empirical_full_min 0.788
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
Cl1 Cl 0.30443(4) 1.03310(4) 0.50624(4) 0.03439(13) Uani 1 1 d . . . . .
F1 F 0.63104(10) 0.81782(10) 0.91964(9) 0.0387(2) Uani 1 1 d . . . . .
F2 F 0.56646(10) 0.98729(9) 0.86841(10) 0.0357(2) Uani 1 1 d . . . . .
F3 F 0.70911(10) 0.85386(11) 0.74221(11) 0.0434(2) Uani 1 1 d . . . . .
O2 O 0.19445(12) 0.51134(10) 0.58187(10) 0.0314(2) Uani 1 1 d . . . . .
O4 O 0.29121(11) 0.70906(10) 0.36962(10) 0.0271(2) Uani 1 1 d . . . . .
O3 O 0.48268(11) 0.60854(11) 0.41666(10) 0.0296(2) Uani 1 1 d . . . . .
N1 N 0.40174(12) 0.78735(12) 0.59961(12) 0.0226(2) Uani 1 1 d . . . . .
O1 O 0.20219(16) 0.49856(13) 0.79474(13) 0.0512(3) Uani 1 1 d . . . . .
C9 C 0.23276(16) 0.56543(15) 0.72458(15) 0.0278(3) Uani 1 1 d . . . . .
C2 C 0.32171(15) 0.72370(14) 0.78739(14) 0.0251(3) Uani 1 1 d . . . . .
H2 H 0.358404 0.760526 0.893403 0.030 Uiso 1 1 calc R U . . .
C8 C 0.28337(14) 0.86097(14) 0.65278(14) 0.0232(3) Uani 1 1 d . . . . .
C11 C 0.39721(15) 0.69167(14) 0.45346(14) 0.0237(3) Uani 1 1 d . . . . .
C16 C 0.59043(15) 0.84950(15) 0.80946(15) 0.0278(3) Uani 1 1 d . . . . .
C1 C 0.45539(14) 0.73687(14) 0.70637(14) 0.0228(3) Uani 1 1 d . . . . .
H1 H 0.482331 0.638604 0.656085 0.027 Uiso 1 1 calc R U . . .
C3 C 0.23238(15) 0.82633(14) 0.76142(14) 0.0250(3) Uani 1 1 d . . . . .
C12 C 0.27522(17) 0.63238(16) 0.20871(15) 0.0310(3) Uani 1 1 d . . . . .
C7 C 0.22922(15) 0.96634(14) 0.62148(15) 0.0270(3) Uani 1 1 d . . . . .
C4 C 0.12023(16) 0.88694(16) 0.83261(16) 0.0318(3) Uani 1 1 d . . . . .
H3 H 0.084932 0.861160 0.905254 0.038 Uiso 1 1 calc R U . . .
C5 C 0.06052(16) 0.98636(17) 0.79532(17) 0.0358(3) Uani 1 1 d . . . . .
H4 H -0.018394 1.027133 0.841045 0.043 Uiso 1 1 calc R U . . .
C14 C 0.4223(2) 0.6680(2) 0.15948(18) 0.0466(4) Uani 1 1 d . . . . .
H12 H 0.459080 0.775213 0.202982 0.070 Uiso 1 1 calc R U . . .
H13 H 0.406318 0.629252 0.053522 0.070 Uiso 1 1 calc R U . . .
H14 H 0.496559 0.622427 0.190143 0.070 Uiso 1 1 calc R U . . .
C10 C 0.11650(19) 0.35842(16) 0.50907(18) 0.0385(4) Uani 1 1 d . . . . .
H6 H 0.097674 0.327839 0.404194 0.058 Uiso 1 1 calc R U . . .
H8 H 0.020702 0.346836 0.543725 0.058 Uiso 1 1 calc R U . . .
H7 H 0.178290 0.296912 0.529920 0.058 Uiso 1 1 calc R U . . .
C6 C 0.11496(16) 1.02646(16) 0.69222(17) 0.0336(3) Uani 1 1 d . . . . .
H5 H 0.074108 1.095876 0.669158 0.040 Uiso 1 1 calc R U . . .
C13 C 0.15629(19) 0.69809(18) 0.15985(17) 0.0380(4) Uani 1 1 d . . . . .
H9 H 0.064535 0.679311 0.198209 0.057 Uiso 1 1 calc R U . . .
H11 H 0.134513 0.652647 0.053623 0.057 Uiso 1 1 calc R U . . .
H10 H 0.192971 0.804779 0.196158 0.057 Uiso 1 1 calc R U . . .
C15 C 0.2181(3) 0.46878(18) 0.1607(2) 0.0518(5) Uani 1 1 d . . . . .
H16 H 0.292895 0.429733 0.199848 0.078 Uiso 1 1 calc R U . . .
H15 H 0.200462 0.417532 0.054541 0.078 Uiso 1 1 calc R U . . .
H17 H 0.123914 0.453195 0.196781 0.078 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 0.0181 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'
Cl Cl 0.3639 0.7018 '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
C9 O2 C10 115.78(11) . . ?
C11 O4 C12 120.82(10) . . ?
C8 N1 C1 106.96(10) . . ?
C11 N1 C8 123.64(10) . . ?
C11 N1 C1 115.98(10) . . ?
O2 C9 C2 110.86(11) . . ?
O1 C9 O2 124.68(13) . . ?
O1 C9 C2 124.46(13) . . ?
C9 C2 H2 110.4 . . ?
C9 C2 C1 111.19(11) . . ?
C1 C2 H2 110.4 . . ?
C3 C2 C9 112.48(11) . . ?
C3 C2 H2 110.4 . . ?
C3 C2 C1 101.71(10) . . ?
C3 C8 N1 110.46(11) . . ?
C7 C8 N1 129.35(12) . . ?
C7 C8 C3 119.82(12) . . ?
O4 C11 N1 110.51(10) . . ?
O3 C11 O4 127.83(12) . . ?
O3 C11 N1 121.66(12) . . ?
F1 C16 F2 106.73(11) . . ?
F1 C16 C1 111.42(11) . . ?
F2 C16 C1 113.21(11) . . ?
F3 C16 F1 107.24(11) . . ?
F3 C16 F2 106.52(12) . . ?
F3 C16 C1 111.38(11) . . ?
N1 C1 C2 105.34(10) . . ?
N1 C1 C16 109.41(10) . . ?
N1 C1 H1 110.3 . . ?
C2 C1 H1 110.3 . . ?
C16 C1 C2 111.16(11) . . ?
C16 C1 H1 110.3 . . ?
C8 C3 C2 109.62(11) . . ?
C4 C3 C2 128.88(13) . . ?
C4 C3 C8 121.45(13) . . ?
O4 C12 C14 110.44(12) . . ?
O4 C12 C13 102.47(11) . . ?
O4 C12 C15 108.48(12) . . ?
C13 C12 C14 110.94(13) . . ?
C15 C12 C14 113.42(15) . . ?
C15 C12 C13 110.52(14) . . ?
C8 C7 Cl1 122.55(10) . . ?
C8 C7 C6 118.59(13) . . ?
C6 C7 Cl1 118.77(11) . . ?
C3 C4 H3 120.8 . . ?
C3 C4 C5 118.42(14) . . ?
C5 C4 H3 120.8 . . ?
C4 C5 H4 119.7 . . ?
C6 C5 C4 120.57(13) . . ?
C6 C5 H4 119.7 . . ?
C12 C14 H12 109.5 . . ?
C12 C14 H13 109.5 . . ?
C12 C14 H14 109.5 . . ?
H12 C14 H13 109.5 . . ?
H12 C14 H14 109.5 . . ?
H13 C14 H14 109.5 . . ?
O2 C10 H6 109.5 . . ?
O2 C10 H8 109.5 . . ?
O2 C10 H7 109.5 . . ?
H6 C10 H8 109.5 . . ?
H6 C10 H7 109.5 . . ?
H8 C10 H7 109.5 . . ?
C7 C6 H5 119.5 . . ?
C5 C6 C7 120.94(13) . . ?
C5 C6 H5 119.5 . . ?
C12 C13 H9 109.5 . . ?
C12 C13 H11 109.5 . . ?
C12 C13 H10 109.5 . . ?
H9 C13 H11 109.5 . . ?
H9 C13 H10 109.5 . . ?
H11 C13 H10 109.5 . . ?
C12 C15 H16 109.5 . . ?
C12 C15 H15 109.5 . . ?
C12 C15 H17 109.5 . . ?
H16 C15 H15 109.5 . . ?
H16 C15 H17 109.5 . . ?
H15 C15 H17 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
Cl1 C7 1.7266(14) . ?
F1 C16 1.3382(16) . ?
F2 C16 1.3414(16) . ?
F3 C16 1.3371(17) . ?
O2 C9 1.3263(17) . ?
O2 C10 1.4454(17) . ?
O4 C11 1.3249(16) . ?
O4 C12 1.4887(16) . ?
O3 C11 1.2098(16) . ?
N1 C8 1.4307(16) . ?
N1 C11 1.4032(16) . ?
N1 C1 1.4704(16) . ?
O1 C9 1.1988(18) . ?
C9 C2 1.5209(18) . ?
C2 H2 1.0000 . ?
C2 C1 1.5520(17) . ?
C2 C3 1.5151(19) . ?
C8 C3 1.3933(19) . ?
C8 C7 1.3880(19) . ?
C16 C1 1.5145(18) . ?
C1 H1 1.0000 . ?
C3 C4 1.3843(19) . ?
C12 C14 1.518(2) . ?
C12 C13 1.517(2) . ?
C12 C15 1.514(2) . ?
C7 C6 1.397(2) . ?
C4 H3 0.9500 . ?
C4 C5 1.389(2) . ?
C5 H4 0.9500 . ?
C5 C6 1.383(2) . ?
C14 H12 0.9800 . ?
C14 H13 0.9800 . ?
C14 H14 0.9800 . ?
C10 H6 0.9800 . ?
C10 H8 0.9800 . ?
C10 H7 0.9800 . ?
C6 H5 0.9500 . ?
C13 H9 0.9800 . ?
C13 H11 0.9800 . ?
C13 H10 0.9800 . ?
C15 H16 0.9800 . ?
C15 H15 0.9800 . ?
C15 H17 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
Cl1 C7 C6 C5 -174.11(12) . . . . ?
F1 C16 C1 N1 171.90(10) . . . . ?
F1 C16 C1 C2 55.98(14) . . . . ?
F2 C16 C1 N1 51.59(15) . . . . ?
F2 C16 C1 C2 -64.33(14) . . . . ?
F3 C16 C1 N1 -68.41(14) . . . . ?
F3 C16 C1 C2 175.67(11) . . . . ?
O2 C9 C2 C1 -51.83(15) . . . . ?
O2 C9 C2 C3 61.50(15) . . . . ?
N1 C8 C3 C2 0.75(14) . . . . ?
N1 C8 C3 C4 178.44(12) . . . . ?
N1 C8 C7 Cl1 -1.2(2) . . . . ?
N1 C8 C7 C6 -177.61(13) . . . . ?
O1 C9 C2 C1 127.83(16) . . . . ?
O1 C9 C2 C3 -118.85(17) . . . . ?
C9 C2 C1 N1 97.40(12) . . . . ?
C9 C2 C1 C16 -144.20(11) . . . . ?
C9 C2 C3 C8 -105.40(12) . . . . ?
C9 C2 C3 C4 77.14(17) . . . . ?
C2 C3 C4 C5 176.00(13) . . . . ?
C8 N1 C11 O4 16.16(16) . . . . ?
C8 N1 C11 O3 -164.45(12) . . . . ?
C8 N1 C1 C2 24.06(12) . . . . ?
C8 N1 C1 C16 -95.51(12) . . . . ?
C8 C3 C4 C5 -1.2(2) . . . . ?
C8 C7 C6 C5 2.4(2) . . . . ?
C11 O4 C12 C14 -55.06(16) . . . . ?
C11 O4 C12 C13 -173.29(12) . . . . ?
C11 O4 C12 C15 69.82(16) . . . . ?
C11 N1 C8 C3 122.87(13) . . . . ?
C11 N1 C8 C7 -64.19(18) . . . . ?
C11 N1 C1 C2 -118.40(11) . . . . ?
C11 N1 C1 C16 122.03(12) . . . . ?
C1 N1 C8 C3 -15.99(13) . . . . ?
C1 N1 C8 C7 156.96(13) . . . . ?
C1 N1 C11 O4 151.72(11) . . . . ?
C1 N1 C11 O3 -28.89(17) . . . . ?
C1 C2 C3 C8 13.63(13) . . . . ?
C1 C2 C3 C4 -163.83(13) . . . . ?
C3 C2 C1 N1 -22.54(12) . . . . ?
C3 C2 C1 C16 95.86(12) . . . . ?
C3 C8 C7 Cl1 171.15(10) . . . . ?
C3 C8 C7 C6 -5.23(19) . . . . ?
C3 C4 C5 C6 -1.7(2) . . . . ?
C12 O4 C11 O3 -6.3(2) . . . . ?
C12 O4 C11 N1 173.07(11) . . . . ?
C7 C8 C3 C2 -172.96(11) . . . . ?
C7 C8 C3 C4 4.7(2) . . . . ?
C4 C5 C6 C7 1.1(2) . . . . ?
C10 O2 C9 O1 -3.0(2) . . . . ?
C10 O2 C9 C2 176.66(12) . . . . ?
