#------------------------------------------------------------------------------
#$Date: 2025-03-04 21:29:52 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298157 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/34/1573402.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_1573402
loop_
_publ_author_name
'Tian, Kui'
'Jin, Zhuan'
'Liu, Xin-Lian'
'He, Ling'
'Liu, Hong-Fu'
'Yu, Pin-Ke'
'Chang, Xin'
'Dong, Xiu-Qin'
'Wang, Chun-Jiang'
_publ_section_title
;
 Stereodivergent assembly of δ-valerolactones with an
 azaarene-containing quaternary stereocenter enabled by Cu/Ru relay
 catalysis.
;
_journal_issue                   3
_journal_name_full               'Chemical science'
_journal_page_first              1233
_journal_page_last               1240
_journal_paper_doi               10.1039/d4sc05852f
_journal_volume                  16
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H16 F N O2'
_chemical_formula_sum            'C17 H16 F N O2'
_chemical_formula_weight         285.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-7-22
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2024-08-02 deposited with the CCDC.	2024-12-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.190(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.47670(10)
_cell_length_b                   15.7755(3)
_cell_length_c                   7.4250(2)
_cell_measurement_reflns_used    6257
_cell_measurement_temperature    300.20(10)
_cell_measurement_theta_max      73.0390
_cell_measurement_theta_min      5.5870
_cell_volume                     746.67(3)
_computing_cell_refinement       'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      300.20(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 1.000
_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     26.00  74.00   0.50    0.20    --   64.58-125.00 -90.00   96
  2  ω     26.00  51.00   0.50    0.20    --   64.58-125.00 -60.00   50
  3  ω     26.00  52.00   0.50    0.20    --   64.58-125.00   0.00   52
  4  ω     28.00  75.00   0.50    0.20    --   64.58-125.00  60.00   94
  5  ω     32.00  63.00   0.50    0.20    --   69.43-125.00  90.00   62
  6  ω     36.00  61.00   0.50    0.20    --   69.43-125.00  60.00   50
  7  ω     65.00 108.00   0.50    0.20    --   69.43  15.00-150.00   86
  8  ω     77.00 102.00   0.50    0.20    --   64.58  15.00-120.00   50
  9  ω     71.00  97.00   0.50    0.20    --   64.58  15.00 -90.00   52
 10  ω     58.00  97.00   0.50    0.20    --   64.58  15.00  90.00   78
 11  ω   -102.00 -38.00   0.50    0.20    --  -76.00 140.00 -78.17  128
 12  ω   -104.00 -70.00   0.50    0.20    --  -77.72 139.00-103.07   68
 13  ω    -97.00 -71.00   0.50    0.20    --  -77.72 128.00 -37.54   52
 14  ω    -90.00 -36.00   0.50    0.20    --  -72.91 125.00-120.00  108
 15  ω    -81.00 -38.00   0.50    0.20    --  -72.91 125.00 -30.00   86
 16  ω    -55.00 -28.00   0.50    0.20    --  -66.36 125.00 -90.00   54
 17  ω    -57.00 -31.00   0.50    0.20    --  -66.36 125.00   0.00   52
 18  ω    -89.00 -34.00   0.50    0.20    --  -72.91 125.00  30.00  110
 19  ω    -55.00 -29.00   0.50    0.20    --  -66.36 125.00 150.00   52
 20  ω    -79.00 -54.00   0.50    0.20    --  -78.57 125.00 150.00   50
 21  ω    -72.00 -39.00   0.50    0.20    --  -72.91 125.00 120.00   66
 22  ω    -94.00 -69.00   0.50    0.20    --  -78.57 125.00  30.00   50
 23  ω    -95.00 -69.00   0.50    0.20    --  -78.57 125.00   0.00   52
 24  ω    -59.00 -29.00   0.50    0.20    --  -66.36 125.00-150.00   60
 25  ω    -95.00 -66.00   0.50    0.20    --  -78.57 125.00-120.00   58
 26  ω    -95.00 -69.00   0.50    0.20    --  -52.00 -22.00 -71.63   52
 27  ω    -92.00 -67.00   0.50    0.20    --  -52.00 -20.00 -61.07   50
 28  ω   -108.00 -83.00   0.50    0.20    --  -66.36 -15.00-120.00   50
 29  ω   -113.00 -70.00   0.50    0.20    --  -72.91 -15.00-150.00   86
 30  ω   -105.00 -77.00   0.50    0.20    --  -68.00 -18.00 -64.20   56
 31  ω   -113.00 -88.00   0.50    0.20    --  -72.91 -15.00 -90.00   50
 32  ω   -102.00 -77.00   0.50    0.20    --  -72.91 -15.00-120.00   50
 33  ω   -102.00 -66.00   0.50    0.20    --  -66.36 -15.00 -30.00   72
 34  ω   -107.00 -67.00   0.50    0.20    --  -72.91 -15.00   0.00   80
 35  ω   -120.00 -95.00   0.50    0.20    --  -78.57 -15.00 -60.00   50
 36  ω   -116.00 -85.00   0.50    0.20    --  -78.57 -15.00 -30.00   62
 37  ω   -107.00 -61.00   0.50    0.20    --  -66.36 -15.00  60.00   92
 38  ω   -107.00 -79.00   0.50    0.20    --  -78.57 -15.00  90.00   56
 39  ω   -113.00 -76.00   0.50    0.20    --  -72.91 -15.00 120.00   74
 40  ω   -104.00 -71.00   0.50    0.20    --  -66.36 -15.00 150.00   66
 41  ω   -102.00 -77.00   0.50    0.20    --  -78.57 -15.00 120.00   50
 42  ω   -105.00 -80.00   0.50    0.20    --  -78.57 -15.00  30.00   50
 43  ω   -119.00 -77.00   0.50    0.20    --  -78.57 -15.00-180.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0092512000
_diffrn_orient_matrix_UB_12      -0.0878539000
_diffrn_orient_matrix_UB_13      0.0915732000
_diffrn_orient_matrix_UB_21      0.2393903000
_diffrn_orient_matrix_UB_22      0.0089662000
_diffrn_orient_matrix_UB_23      0.0582142000
_diffrn_orient_matrix_UB_31      -0.0319451000
_diffrn_orient_matrix_UB_32      0.0416562000
_diffrn_orient_matrix_UB_33      0.1807492000
_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  0.0144
_diffrn_reflns_av_unetI/netI     0.0125
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            9329
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.689
_diffrn_reflns_theta_min         5.609
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.755
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.98a (Rigaku Oxford Diffraction, 2023)
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    1.269
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 1191 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(6)
_refine_ls_extinction_coef       0.0104(18)
_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     192
_refine_ls_number_reflns         2845
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0336
_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)+(0.0590P)²+0.0244P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.0945
_reflns_Friedel_coverage         0.856
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.889
_reflns_number_gt                2694
_reflns_number_total             2845
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc05852f2.cif
_cod_data_source_block           TK-lactone
_cod_depositor_comments          'Adding full bibliography for 1573402.cif.'
_cod_database_code               1573402
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N F'
_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   0.805
_shelx_estimated_absorpt_t_min   0.660
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00E(H00E)
2.b Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B), C00H(H00H,H00I)
2.c Aromatic/amide H refined with riding coordinates:
 C009(H009), C00C(H00C), C00D(H00D), C00F(H00F), C00G(H00G), C00I(H00J),
 C00J(H00K), C00L(H00O)
2.d Idealised Me refined as rotating group:
 C00K(H00L,H00M,H00N)
;
_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 1.422
_oxdiff_exptl_absorpt_empirical_full_min 0.720
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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
O1 O 0.1232(2) 0.48276(11) 0.4059(2) 0.0741(4) Uani 1 1 d . . . . .
O2 O 0.1201(3) 0.59146(11) 0.2275(2) 0.0841(5) Uani 1 1 d . . . . .
F1 F -0.2088(5) 0.34349(17) 1.0793(3) 0.1395(9) Uani 1 1 d . . . . .
C004 C 0.2246(3) 0.54083(15) 0.3247(3) 0.0687(5) Uani 1 1 d . . . . .
N1 N 0.3911(3) 0.63550(16) 0.6005(3) 0.0885(6) Uani 1 1 d . . . . .
C006 C 0.1020(3) 0.38900(13) 0.6538(3) 0.0697(5) Uani 1 1 d . . . . .
C007 C 0.5370(3) 0.60162(13) 0.5187(3) 0.0645(5) Uani 1 1 d . . . . .
C008 C 0.4651(3) 0.54209(17) 0.3583(3) 0.0726(5) Uani 1 1 d . . . . .
C009 C 0.7479(3) 0.61905(17) 0.5758(4) 0.0826(6) Uani 1 1 d . . . . .
H009 H 0.848162 0.595343 0.515414 0.099 Uiso 1 1 calc R U . . .
C00A C 0.4540(4) 0.41564(17) 0.5571(4) 0.0857(7) Uani 1 1 d . . . . .
H00A H 0.484616 0.452262 0.663453 0.103 Uiso 1 1 calc R U . . .
H00B H 0.515067 0.360460 0.590497 0.103 Uiso 1 1 calc R U . . .
C00B C -0.1056(5) 0.35824(19) 0.9377(4) 0.0918(7) Uani 1 1 d . . . . .
C00C C 0.4538(5) 0.6881(2) 0.7409(4) 0.1040(10) Uani 1 1 d . . . . .
H00C H 0.351494 0.712923 0.797255 0.125 Uiso 1 1 calc R U . . .
C00D C -0.0255(5) 0.43699(18) 0.9225(3) 0.0868(7) Uani 1 1 d . . . . .
H00D H -0.041694 0.479472 1.005714 0.104 Uiso 1 1 calc R U . . .
C00E C 0.2183(4) 0.40694(15) 0.4991(3) 0.0745(5) Uani 1 1 d . . . . .
H00E H 0.192118 0.359585 0.412609 0.089 Uiso 1 1 calc R U . . .
C00F C 0.0809(4) 0.45221(15) 0.7795(3) 0.0769(6) Uani 1 1 d . . . . .
H00F H 0.138954 0.505393 0.767517 0.092 Uiso 1 1 calc R U . . .
C00G C 0.0176(5) 0.31038(14) 0.6767(4) 0.0833(6) Uani 1 1 d . . . . .
H00G H 0.030915 0.267336 0.593978 0.100 Uiso 1 1 calc R U . . .
C00H C 0.5491(4) 0.45228(18) 0.4037(4) 0.0884(7) Uani 1 1 d . . . . .
H00H H 0.514986 0.416548 0.296277 0.106 Uiso 1 1 calc R U . . .
H00I H 0.700533 0.454016 0.439142 0.106 Uiso 1 1 calc R U . . .
C00I C -0.0866(5) 0.29422(18) 0.8206(5) 0.0951(8) Uani 1 1 d . . . . .
H00J H -0.141881 0.240871 0.836253 0.114 Uiso 1 1 calc R U . . .
C00J C 0.6576(5) 0.7076(2) 0.8064(4) 0.0964(8) Uani 1 1 d . . . . .
H00K H 0.693981 0.744260 0.905051 0.116 Uiso 1 1 calc R U . . .
C00K C 0.5376(5) 0.5762(3) 0.1860(4) 0.1016(9) Uani 1 1 d . . . . .
H00L H 0.482363 0.541029 0.083295 0.152 Uiso 1 1 calc R U . . .
H00M H 0.688056 0.575800 0.204118 0.152 Uiso 1 1 calc R U . . .
H00N H 0.487611 0.633176 0.163019 0.152 Uiso 1 1 calc R U . . .
C00L C 0.8067(4) 0.6717(2) 0.7224(4) 0.0953(8) Uani 1 1 d . . . . .
H00O H 0.947935 0.682922 0.764577 0.114 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'
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
C004 O1 C00E 125.19(16) . . ?
O1 C004 C008 120.23(19) . . ?
O2 C004 O1 117.28(18) . . ?
O2 C004 C008 122.5(2) . . ?
C007 N1 C00C 117.7(2) . . ?
C00F C006 C00E 119.9(2) . . ?
C00G C006 C00E 121.7(2) . . ?
C00G C006 C00F 118.3(2) . . ?
N1 C007 C008 117.61(18) . . ?
N1 C007 C009 121.7(2) . . ?
C009 C007 C008 120.7(2) . . ?
C004 C008 C00H 109.5(2) . . ?
C004 C008 C00K 108.68(19) . . ?
C007 C008 C004 107.24(17) . . ?
C007 C008 C00H 110.50(19) . . ?
C007 C008 C00K 109.8(2) . . ?
C00H C008 C00K 111.0(2) . . ?
C007 C009 H009 120.5 . . ?
C00L C009 C007 119.0(2) . . ?
C00L C009 H009 120.5 . . ?
H00A C00A H00B 108.1 . . ?
C00E C00A H00A 109.6 . . ?
C00E C00A H00B 109.6 . . ?
C00H C00A H00A 109.6 . . ?
C00H C00A H00B 109.6 . . ?
C00H C00A C00E 110.2(2) . . ?
C00D C00B F1 117.8(3) . . ?
C00I C00B F1 118.8(3) . . ?
C00I C00B C00D 123.4(3) . . ?
N1 C00C H00C 117.9 . . ?
N1 C00C C00J 124.1(3) . . ?
C00J C00C H00C 117.9 . . ?
C00B C00D H00D 120.9 . . ?
C00B C00D C00F 118.1(2) . . ?
C00F C00D H00D 120.9 . . ?
O1 C00E C006 106.77(16) . . ?
O1 C00E C00A 112.28(19) . . ?
O1 C00E H00E 107.7 . . ?
C006 C00E C00A 114.4(2) . . ?
C006 C00E H00E 107.7 . . ?
C00A C00E H00E 107.7 . . ?
C006 C00F H00F 119.6 . . ?
C00D C00F C006 120.8(2) . . ?
C00D C00F H00F 119.6 . . ?
C006 C00G H00G 119.3 . . ?
C006 C00G C00I 121.3(2) . . ?
C00I C00G H00G 119.3 . . ?
C008 C00H H00H 109.6 . . ?
C008 C00H H00I 109.6 . . ?
C00A C00H C008 110.19(18) . . ?
C00A C00H H00H 109.6 . . ?
C00A C00H H00I 109.6 . . ?
H00H C00H H00I 108.1 . . ?
C00B C00I C00G 118.1(3) . . ?
C00B C00I H00J 121.0 . . ?
C00G C00I H00J 121.0 . . ?
C00C C00J H00K 121.2 . . ?
C00C C00J C00L 117.7(3) . . ?
C00L C00J H00K 121.2 . . ?
C008 C00K H00L 109.5 . . ?
C008 C00K H00M 109.5 . . ?
C008 C00K H00N 109.5 . . ?
H00L C00K H00M 109.5 . . ?
H00L C00K H00N 109.5 . . ?
H00M C00K H00N 109.5 . . ?
C009 C00L H00O 120.1 . . ?
C00J C00L C009 119.8(2) . . ?
C00J C00L H00O 120.1 . . ?
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
O1 C004 1.332(3) . ?
O1 C00E 1.462(3) . ?
O2 C004 1.202(3) . ?
F1 C00B 1.362(3) . ?
C004 C008 1.533(3) . ?
N1 C007 1.323(3) . ?
N1 C00C 1.339(4) . ?
C006 C00E 1.508(3) . ?
C006 C00F 1.389(3) . ?
C006 C00G 1.378(3) . ?
C007 C008 1.523(3) . ?
C007 C009 1.385(3) . ?
C008 C00H 1.534(4) . ?
C008 C00K 1.536(4) . ?
C009 H009 0.9300 . ?
C009 C00L 1.369(4) . ?
C00A H00A 0.9700 . ?
C00A H00B 0.9700 . ?
C00A C00E 1.517(3) . ?
C00A C00H 1.503(4) . ?
C00B C00D 1.359(4) . ?
C00B C00I 1.352(5) . ?
C00C H00C 0.9300 . ?
C00C C00J 1.358(4) . ?
C00D H00D 0.9300 . ?
C00D C00F 1.385(3) . ?
C00E H00E 0.9800 . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00G C00I 1.384(4) . ?
C00H H00H 0.9700 . ?
C00H H00I 0.9700 . ?
C00I H00J 0.9300 . ?
C00J H00K 0.9300 . ?
C00J C00L 1.362(4) . ?
C00K H00L 0.9600 . ?
C00K H00M 0.9600 . ?
C00K H00N 0.9600 . ?
C00L H00O 0.9300 . ?
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
O1 C004 C008 C007 -91.9(2) . . . . ?
O1 C004 C008 C00H 28.0(3) . . . . ?
O1 C004 C008 C00K 149.4(2) . . . . ?
O2 C004 C008 C007 87.3(2) . . . . ?
O2 C004 C008 C00H -152.7(2) . . . . ?
O2 C004 C008 C00K -31.3(3) . . . . ?
F1 C00B C00D C00F 179.6(3) . . . . ?
F1 C00B C00I C00G 179.6(3) . . . . ?
C004 O1 C00E C006 147.57(19) . . . . ?
C004 O1 C00E C00A 21.4(3) . . . . ?
C004 C008 C00H C00A -52.6(3) . . . . ?
N1 C007 C008 C004 3.3(3) . . . . ?
N1 C007 C008 C00H -116.0(2) . . . . ?
N1 C007 C008 C00K 121.2(2) . . . . ?
N1 C007 C009 C00L 1.0(4) . . . . ?
N1 C00C C00J C00L 0.5(5) . . . . ?
C006 C00G C00I C00B 0.7(4) . . . . ?
C007 N1 C00C C00J -1.2(5) . . . . ?
C007 C008 C00H C00A 65.3(2) . . . . ?
C007 C009 C00L C00J -1.7(4) . . . . ?
C008 C007 C009 C00L -178.9(2) . . . . ?
C009 C007 C008 C004 -176.8(2) . . . . ?
C009 C007 C008 C00H 63.9(3) . . . . ?
C009 C007 C008 C00K -58.9(3) . . . . ?
C00B C00D C00F C006 1.0(4) . . . . ?
C00C N1 C007 C008 -179.7(3) . . . . ?
C00C N1 C007 C009 0.4(4) . . . . ?
C00C C00J C00L C009 1.0(5) . . . . ?
C00D C00B C00I C00G -0.9(5) . . . . ?
C00E O1 C004 O2 167.5(2) . . . . ?
C00E O1 C004 C008 -13.2(3) . . . . ?
C00E C006 C00F C00D 179.9(2) . . . . ?
C00E C006 C00G C00I 179.2(2) . . . . ?
C00E C00A C00H C008 63.1(3) . . . . ?
C00F C006 C00E O1 -53.2(3) . . . . ?
C00F C006 C00E C00A 71.6(3) . . . . ?
C00F C006 C00G C00I 0.2(4) . . . . ?
C00G C006 C00E O1 127.9(2) . . . . ?
C00G C006 C00E C00A -107.3(3) . . . . ?
C00G C006 C00F C00D -1.1(3) . . . . ?
C00H C00A C00E O1 -45.4(3) . . . . ?
C00H C00A C00E C006 -167.3(2) . . . . ?
C00I C00B C00D C00F 0.0(5) . . . . ?
C00K C008 C00H C00A -172.6(2) . . . . ?
