#------------------------------------------------------------------------------
#$Date: 2025-08-20 21:34:49 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301835 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/49/4134955.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_4134955
loop_
_publ_author_name
'Tian, Chong'
'Fielden, Stephen D. P.'
'Pérez-Saavedra, Borja'
'Vitorica-Yrezabal, Iñigo J'
'Leigh, David A.'
_publ_section_title
;
 Single-Step Enantioselective Synthesis of Mechanically Planar Chiral
 [2]Rotaxanes Using a Chiral Leaving Group Strategy.
;
_journal_issue                   21
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9803
_journal_page_last               9808
_journal_paper_doi               10.1021/jacs.0c03447
_journal_volume                  142
_journal_year                    2020
_chemical_formula_moiety         'C28 H33 N O10, C24 H27 F6 N O, 2(C3 H8 O)'
_chemical_formula_sum            'C58 H76 F6 N2 O13'
_chemical_formula_weight         1123.20
_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     direct
_audit_creation_date             2019-11-28
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_cell_angle_alpha                74.834(3)
_cell_angle_beta                 76.745(2)
_cell_angle_gamma                81.664(2)
_cell_formula_units_Z            2
_cell_length_a                   13.2744(3)
_cell_length_b                   14.5586(4)
_cell_length_c                   16.0139(5)
_cell_measurement_reflns_used    29877
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      75.7620
_cell_measurement_theta_min      2.8860
_cell_volume                     2895.51(14)
_computing_cell_refinement       'CrysAlisPro 1.171.40.58a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.58a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.58a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS n/a (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -34.00  54.00   1.00    2.00    --    5.00  38.00  30.00   88
  2  ω    -35.00  93.00   1.00    2.00    --    5.00  76.00-180.00  128
  3  ω    -94.00 -55.00   1.00    2.00    --  -45.90 -76.00   0.00   39
  4  ω    -31.00  -6.00   1.00    2.00    --  -45.90 -76.00   0.00   25
  5  ω    -85.00  42.00   1.00    2.00    --  -45.90  76.00  90.00  127
  6  ω    -40.00  -6.00   1.00    2.00    --  -45.90 -76.00 120.00   34
  7  ω   -130.00 -97.00   1.00    2.00    --  -45.90 -76.00   0.00   33
  8  ω   -134.00 -50.00   1.00    2.00    --  -45.90 -76.00 120.00   84
  9  ω   -150.00-123.00   1.00    2.00    --  -62.00 -76.00 111.21   27
 10  ω    -58.00 -22.00   1.00    2.00    --  -62.00 -76.00 -69.02   36
 11  ω   -137.00-110.00   1.00    2.00    --  -62.00 -76.00 -69.02   27
 12  ω    -53.00 -22.00   1.00    2.00    --  -62.00 -76.00 111.21   31
 13  ω    -61.00 -26.00   1.00    2.00    --  -66.00 -76.00 -18.34   35
 14  ω   -145.00-119.00   1.00    2.00    --  -66.00 -76.00   9.50   26
 15  ω    -56.00 -26.00   1.00    2.00    --  -66.00 -76.00-130.77   30
 16  ω   -154.00-128.00   1.00    2.00    --  -66.00 -76.00-130.77   26
 17  ω    -60.00 -27.00   1.00    2.00    --  -66.00 -75.00 -86.34   33
 18  ω    -52.00 -26.00   1.00    2.00    --  -66.00 -76.00   9.50   26
 19  ω    -59.00 -34.00   1.00    2.00    --  -74.00 -76.00-172.03   25
 20  ω   -120.00 -95.00   1.00    2.00    --  -74.00 -76.00-172.03   25
 21  ω   -160.00-135.00   1.00    2.00    --  -74.00 -75.00  94.85   25
 22  ω    -60.00 -35.00   1.00    2.00    --  -74.00 -75.00  94.85   25
 23  ω    -61.00 -34.00   1.00    2.00    --  -74.00 -76.00 -41.03   27
 24  ω   -164.00-139.00   1.00    7.00    --  -78.00 -74.00 164.81   25
 25  ω    -64.00 -39.00   1.00    7.00    --  -78.00 -74.00 164.81   25
 26  ω    -72.00 -43.00   1.00    7.00    --  -82.00 -74.00 137.51   29
 27  ω    -70.00 -43.00   1.00    7.00    --  -82.00 -74.00  42.58   27
 28  ω   -169.00-142.00   1.00    7.00    --  -82.00 -76.00  77.09   27
 29  ω    -68.00 -42.00   1.00    7.00    --  -82.00 -76.00  77.09   26
 30  ω    -73.00 -47.00   1.00    7.00    --  -86.00 -74.00 104.05   26
 31  ω    -74.00 -47.00   1.00    7.00    --  -86.00 -75.00-112.41   27
 32  ω    -77.00 -51.00   1.00    7.00    --  -90.00 -75.00 -73.12   26
 33  ω   -101.00 -55.00   1.00    7.00    --  -94.00 -75.00-124.08   46
 34  ω   -178.00-107.00   1.00    7.00    --  -94.00 -75.00-124.08   71
 35  ω   -113.00 -59.00   1.00    7.00    --  -94.00 -67.00  90.94   54
 36  ω   -182.00-120.00   1.00    7.00    --  -94.00 -67.00  90.94   62
 37  ω   -107.00 -55.00   1.00    7.00    --  -94.00 -75.00  17.44   52
 38  ω   -180.00-108.00   1.00    7.00    --  -94.00 -75.00  17.44   72
 39  ω   -162.00 -57.00   1.00    7.00    --  -94.00 -70.00  26.06  105
 40  ω    -98.00 -55.00   1.00    7.00    --  -94.00 -75.00 -31.72   43
 41  ω   -183.00-109.00   1.00    7.00    --  -94.00 -75.00 -31.72   74
 42  ω   -151.00 -55.00   1.00    7.00    --  -94.00 -75.00 -51.14   96
 43  ω    -85.00 -58.00   1.00    7.00    --  -98.00 -76.00 151.70   27
 44  ω   -184.00 -89.00   1.00    7.00    --  -98.00 -76.00 151.70   95
 45  ω   -165.00 -60.00   1.00    7.00    --  -98.00 -73.00  83.46  105
 46  ω   -176.00 -64.00   1.00    7.00    --  -98.00 -73.00-162.66  112
 47  ω   -185.00 -60.00   1.00    7.00    --  -98.00 -72.00-176.71  125
 48  ω    -90.00 -60.00   1.00    7.00    --  -98.00 -72.00 -80.87   30
 49  ω   -141.00 -59.00   1.00    7.00    --  -98.00 -75.00-142.40   82
 50  ω   -184.00 -94.00   1.00    7.00    --  -98.00 -72.00 -80.87   90
 51  ω   -191.00 -64.00   1.00    7.00    -- -102.00 -73.00  63.28  127
 52  ω   -170.00 -64.00   1.00    7.00    -- -102.00 -72.00  -7.77  106
 53  ω   -102.00 -51.00   1.00    7.00    -- -107.20  76.00  90.00   51
 54  ω   -148.00 -20.00   1.00    7.00    -- -107.20  76.00 120.00  128
 55  ω   -112.00 -52.00   1.00    7.00    -- -107.20  76.00 -30.00   60
 56  ω   -137.00 -68.00   1.00    7.00    -- -107.20  76.00 -90.00   69
 57  ω   -194.00 -68.00   1.00    7.00    -- -107.20 -74.00 133.42  126
 58  ω   -196.00 -67.00   1.00    7.00    -- -107.20 -76.00 -90.00  129
 59  ω   -115.00 -40.00   1.00    7.00    -- -107.20  76.00-150.00   75
 60  ω   -119.00 -51.00   1.00    7.00    -- -107.20  76.00  30.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1184301000
_diffrn_orient_matrix_UB_12      -0.0021997000
_diffrn_orient_matrix_UB_13      -0.0343808000
_diffrn_orient_matrix_UB_21      -0.0162101000
_diffrn_orient_matrix_UB_22      0.0122089000
_diffrn_orient_matrix_UB_23      -0.0946608000
_diffrn_orient_matrix_UB_31      -0.0067101000
_diffrn_orient_matrix_UB_32      0.1093867000
_diffrn_orient_matrix_UB_33      -0.0144058000
_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  0.0379
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            71520
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.200
_diffrn_reflns_theta_min         2.918
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    0.867
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.58a (Rigaku Oxford Diffraction, 2019)
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    1.288
_exptl_crystal_description       plank
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.00108(10)
_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   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     765
_refine_ls_number_reflns         11495
_refine_ls_number_restraints     114
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0455
_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)+(0.0457P)²+1.7920P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1132
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10183
_reflns_number_total             11495
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c03447_si_002.cif
_cod_data_source_block           rdl43
_cod_depositor_comments          'Adding full bibliography for 4134955.cif.'
_cod_database_code               4134955
_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   0.974
_shelx_estimated_absorpt_t_min   0.874
_reflns_odcompleteness_completeness 99.31
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O76-C77 \\sim O76A-C77A
 with sigma of 0.02
 C77-C79 \\sim C77A-C79A
 with sigma of 0.02
 C77-C78 \\sim C77A-C78A
 with sigma of 0.02
 O76-C79 \\sim O76A-C79A
 with sigma of 0.04
 O76-C78 \\sim O76A-C78A
 with sigma of 0.04
 C79-C78 \\sim C79A-C78A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C78A \\sim O76 \\sim C77 \\sim C79 \\sim C78 \\sim C77A \\sim O76A \\sim C79A:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
4. Others
 Sof(C77A)=Sof(H77A)=Sof(C78A)=Sof(H78D)=Sof(H78E)=Sof(H78F)=Sof(C79A)=
 Sof(H79D)=Sof(H79E)=Sof(H79F)=Sof(O76A)=Sof(H76A)=1-FVAR(1)
 Sof(O76)=Sof(H76)=Sof(C77)=Sof(H77)=Sof(C79)=Sof(H79A)=Sof(H79B)=Sof(H79C)=
 Sof(C78)=Sof(H78A)=Sof(H78B)=Sof(H78C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C73(H73), C77(H77), C77A(H77A)
5.b Secondary CH2 refined with riding coordinates:
 C46(H46A,H46B), C28(H28A,H28B), C17(H17A,H17B), C12(H12A,H12B), C18(H18A,
 H18B), C5(H5A,H5B), C15(H15A,H15B), C27(H27A,H27B), C6(H6A,H6B), C14(H14A,
 H14B), C8(H8A,H8B), C11(H11A,H11B), C9(H9A,H9B)
5.c Aromatic/amide H refined with riding coordinates:
 N47(H47), C61(H61), C41(H41), C21(H21), C59(H59), C43(H43), C63(H63),
 C45(H45), C2(H2), C31(H31), C35(H35), C22(H22), C33(H33), C36(H36), C24(H24),
 C34(H34)
5.d Idealised Me refined as rotating group:
 C66(H66A,H66B,H66C), C65(H65A,H65B,H65C), C69(H69A,H69B,H69C), C67(H67A,H67B,
 H67C), C70(H70A,H70B,H70C), C71(H71A,H71B,H71C), C75(H75A,H75B,H75C), C74(H74A,
 H74B,H74C), C79(H79A,H79B,H79C), C78(H78A,H78B,H78C), C78A(H78D,H78E,H78F),
 C79A(H79D,H79E,H79F)
5.e Idealised tetrahedral OH refined as rotating group:
 O72(H72), O76(H76), O76A(H76A)
;
_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 1.210
_oxdiff_exptl_absorpt_empirical_full_min 0.824
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
O16 O 0.05540(8) 0.89765(8) 0.15468(7) 0.0246(2) Uani 1 1 d . . . . .
F51 F 0.12294(12) 0.67884(8) -0.09173(7) 0.0521(3) Uani 1 1 d . . . . .
O26 O 0.41549(8) 0.80816(8) 0.05839(8) 0.0255(2) Uani 1 1 d . . . . .
F55 F -0.02502(11) 0.43416(8) 0.16340(8) 0.0525(3) Uani 1 1 d . . . . .
F56 F -0.09889(8) 0.50589(8) 0.26574(9) 0.0474(3) Uani 1 1 d . . . . .
F57 F 0.03758(9) 0.41025(7) 0.28045(7) 0.0410(3) Uani 1 1 d . . . . .
O29 O 0.40529(8) 0.59975(8) 0.08603(7) 0.0249(2) Uani 1 1 d . . . . .
O7 O 0.21364(9) 0.49083(8) 0.41340(7) 0.0284(2) Uani 1 1 d . . . . .
O4 O 0.34044(9) 0.47501(8) 0.22993(7) 0.0269(2) Uani 1 1 d . . . . .
O10 O 0.06246(9) 0.63924(8) 0.42685(7) 0.0307(3) Uani 1 1 d . . . . .
O19 O 0.26889(8) 0.93653(8) 0.08997(7) 0.0248(2) Uani 1 1 d . . . . .
F53 F 0.20444(11) 0.78553(11) -0.07546(8) 0.0593(4) Uani 1 1 d . . . . .
O49 O 0.32380(9) 0.76217(9) 0.35091(9) 0.0346(3) Uani 1 1 d . . . . .
F52 F 0.03950(10) 0.79909(9) -0.04730(8) 0.0581(4) Uani 1 1 d . . . . .
O13 O -0.05130(9) 0.78717(8) 0.30488(7) 0.0274(2) Uani 1 1 d . . . . .
N47 N 0.20230(10) 0.78200(9) 0.27000(8) 0.0208(3) Uani 1 1 d . . . . .
H47 H 0.149907 0.815735 0.250790 0.025 Uiso 1 1 calc R U . . .
C61 C 0.15213(12) 1.08163(11) 0.38483(10) 0.0238(3) Uani 1 1 d . . . . .
H61 H 0.133370 1.141619 0.396861 0.029 Uiso 1 1 calc R U . . .
O39 O 0.73364(10) 0.91775(11) 0.10864(9) 0.0426(3) Uani 1 1 d . . . . .
O72 O 0.47750(10) 0.69769(13) 0.61307(10) 0.0495(4) Uani 1 1 d . . . . .
H72 H 0.471322 0.710480 0.561387 0.074 Uiso 1 1 calc R U . . .
C41 C 0.17741(11) 0.71326(11) 0.10420(10) 0.0217(3) Uani 1 1 d . . . . .
H41 H 0.216301 0.765460 0.078892 0.026 Uiso 1 1 calc R U . . .
O38 O 0.67796(12) 1.04039(12) 0.16362(12) 0.0566(4) Uani 1 1 d . . . . .
C40 C 0.17589(11) 0.66530(11) 0.19162(10) 0.0212(3) Uani 1 1 d . . . . .
C58 C 0.20915(12) 0.90510(11) 0.34613(10) 0.0214(3) Uani 1 1 d . . . . .
C46 C 0.24212(12) 0.69210(11) 0.24492(10) 0.0222(3) Uani 1 1 d . . . . .
H46A H 0.244964 0.641613 0.297858 0.027 Uiso 1 1 calc R U . . .
H46B H 0.312346 0.697639 0.210633 0.027 Uiso 1 1 calc R U . . .
C48 C 0.24826(12) 0.81103(11) 0.32307(10) 0.0223(3) Uani 1 1 d . . . . .
C42 C 0.12101(12) 0.68356(11) 0.05435(10) 0.0234(3) Uani 1 1 d . . . . .
C23 C 0.55869(13) 0.96679(12) 0.12339(11) 0.0286(3) Uani 1 1 d . . . . .
C44 C 0.05995(12) 0.55884(11) 0.17836(11) 0.0250(3) Uani 1 1 d . . . . .
C21 C 0.38048(13) 1.02557(12) 0.13562(11) 0.0275(3) Uani 1 1 d . . . . .
H21 H 0.326273 1.070511 0.149955 0.033 Uiso 1 1 calc R U . . .
C59 C 0.27592(12) 0.94666(11) 0.37757(10) 0.0237(3) Uani 1 1 d . . . . .
H59 H 0.340534 0.914844 0.384629 0.028 Uiso 1 1 calc R U . . .
C43 C 0.06210(12) 0.60577(11) 0.09083(11) 0.0251(3) Uani 1 1 d . . . . .
H43 H 0.024963 0.585727 0.057158 0.030 Uiso 1 1 calc R U . . .
C62 C 0.08225(12) 1.04199(11) 0.35334(10) 0.0216(3) Uani 1 1 d . . . . .
C28 C 0.44788(12) 0.66639(11) 0.00694(10) 0.0251(3) Uani 1 1 d . . . . .
H28A H 0.393434 0.697856 -0.024786 0.030 Uiso 1 1 calc R U . . .
H28B H 0.499573 0.633384 -0.031220 0.030 Uiso 1 1 calc R U . . .
C63 C 0.11149(12) 0.95209(11) 0.33550(10) 0.0214(3) Uani 1 1 d . . . . .
H63 H 0.065846 0.923127 0.316403 0.026 Uiso 1 1 calc R U . . .
N37 N 0.66375(12) 0.97578(12) 0.13231(10) 0.0365(3) Uani 1 1 d . . . . .
C66 C 0.35779(14) 1.00352(13) 0.51360(12) 0.0325(4) Uani 1 1 d . . . . .
H66A H 0.393637 0.948187 0.494384 0.049 Uiso 1 1 calc R U . . .
H66B H 0.297601 0.985307 0.558352 0.049 Uiso 1 1 calc R U . . .
H66C H 0.403254 1.030915 0.537316 0.049 Uiso 1 1 calc R U . . .
C17 C 0.08996(12) 0.97706(11) 0.08577(10) 0.0262(3) Uani 1 1 d . . . . .
H17A H 0.035289 1.029126 0.083216 0.031 Uiso 1 1 calc R U . . .
H17B H 0.106301 0.959249 0.029554 0.031 Uiso 1 1 calc R U . . .
C12 C -0.09113(13) 0.70760(12) 0.37102(11) 0.0295(4) Uani 1 1 d . . . . .
H12A H -0.080467 0.652019 0.346262 0.035 Uiso 1 1 calc R U . . .
H12B H -0.165276 0.721078 0.390750 0.035 Uiso 1 1 calc R U . . .
C25 C 0.44334(12) 0.88027(11) 0.08560(10) 0.0226(3) Uani 1 1 d . . . . .
C45 C 0.11625(12) 0.58834(11) 0.22873(10) 0.0228(3) Uani 1 1 d . . . . .
H45 H 0.113845 0.556299 0.287487 0.027 Uiso 1 1 calc R U . . .
C60 C 0.24816(12) 1.03522(11) 0.39884(10) 0.0238(3) Uani 1 1 d . . . . .
C2 C 0.28335(12) 0.37815(12) 0.14958(11) 0.0277(3) Uani 1 1 d . . . . .
H2 H 0.265658 0.330372 0.200405 0.033 Uiso 1 1 calc R U . . .
C31 C 0.34285(12) 0.51882(12) -0.00394(11) 0.0265(3) Uani 1 1 d . . . . .
H31 H 0.364073 0.565326 -0.054928 0.032 Uiso 1 1 calc R U . . .
C18 C 0.18468(12) 1.00883(11) 0.10229(11) 0.0251(3) Uani 1 1 d . . . . .
H18A H 0.201704 1.069235 0.061459 0.030 Uiso 1 1 calc R U . . .
H18B H 0.172002 1.017395 0.162007 0.030 Uiso 1 1 calc R U . . .
C35 C 0.20100(14) 0.28450(13) -0.01857(14) 0.0379(4) Uani 1 1 d . . . . .
H35 H 0.170246 0.232414 -0.021845 0.045 Uiso 1 1 calc R U . . .
C5 C 0.31376(14) 0.40389(12) 0.31072(11) 0.0290(3) Uani 1 1 d . . . . .
H5A H 0.363523 0.348062 0.310983 0.035 Uiso 1 1 calc R U . . .
H5B H 0.245344 0.384452 0.315670 0.035 Uiso 1 1 calc R U . . .
C15 C -0.04979(12) 0.88362(12) 0.15792(11) 0.0268(3) Uani 1 1 d . . . . .
H15A H -0.058190 0.881808 0.099797 0.032 Uiso 1 1 calc R U . . .
H15B H -0.095658 0.936369 0.175713 0.032 Uiso 1 1 calc R U . . .
C27 C 0.49669(12) 0.73846(11) 0.03293(11) 0.0264(3) Uani 1 1 d . . . . .
H27A H 0.530918 0.707614 0.081809 0.032 Uiso 1 1 calc R U . . .
H27B H 0.548037 0.768825 -0.016348 0.032 Uiso 1 1 calc R U . . .
C6 C 0.31456(13) 0.44539(13) 0.38720(11) 0.0307(4) Uani 1 1 d . . . . .
H6A H 0.332561 0.395144 0.436105 0.037 Uiso 1 1 calc R U . . .
H6B H 0.365876 0.491532 0.369963 0.037 Uiso 1 1 calc R U . . .
C68 C -0.02057(12) 1.09973(11) 0.33760(10) 0.0241(3) Uani 1 1 d . . . . .
C22 C 0.48007(14) 1.03426(12) 0.14514(11) 0.0297(4) Uani 1 1 d . . . . .
H22 H 0.493126 1.084566 0.165751 0.036 Uiso 1 1 calc R U . . .
C20 C 0.36158(12) 0.95026(11) 0.10488(10) 0.0234(3) Uani 1 1 d . . . . .
C30 C 0.35878(12) 0.52722(11) 0.07513(10) 0.0239(3) Uani 1 1 d . . . . .
C65 C 0.41957(14) 1.10279(14) 0.36140(13) 0.0376(4) Uani 1 1 d . . . . .
H65A H 0.398159 1.147887 0.311691 0.056 Uiso 1 1 calc R U . . .
H65B H 0.453301 1.046010 0.343673 0.056 Uiso 1 1 calc R U . . .
H65C H 0.467017 1.130414 0.382858 0.056 Uiso 1 1 calc R U . . .
C14 C -0.07796(12) 0.79136(12) 0.22271(11) 0.0269(3) Uani 1 1 d . . . . .
H14A H -0.151964 0.786544 0.231563 0.032 Uiso 1 1 calc R U . . .
H14B H -0.041289 0.737970 0.199294 0.032 Uiso 1 1 calc R U . . .
C33 C 0.27516(14) 0.43194(13) -0.09099(13) 0.0346(4) Uani 1 1 d . . . . .
H33 H 0.293961 0.478813 -0.142286 0.041 Uiso 1 1 calc R U . . .
C3 C 0.32610(12) 0.45618(11) 0.15453(10) 0.0245(3) Uani 1 1 d . . . . .
C50 C 0.12196(13) 0.73572(12) -0.03944(11) 0.0273(3) Uani 1 1 d . . . . .
C64 C 0.32401(13) 1.07731(12) 0.43489(11) 0.0281(3) Uani 1 1 d . . . . .
C69 C -0.07924(14) 1.13226(14) 0.42061(11) 0.0337(4) Uani 1 1 d . . . . .
H69A H -0.090512 1.077515 0.469304 0.051 Uiso 1 1 calc R U . . .
H69B H -0.144983 1.165358 0.410560 0.051 Uiso 1 1 calc R U . . .
H69C H -0.038996 1.174290 0.433985 0.051 Uiso 1 1 calc R U . . .
C8 C 0.21144(14) 0.54719(13) 0.47469(11) 0.0312(4) Uani 1 1 d . . . . .
H8A H 0.255636 0.598907 0.447283 0.037 Uiso 1 1 calc R U . . .
H8B H 0.237344 0.508060 0.525800 0.037 Uiso 1 1 calc R U . . .
C67 C 0.27519(15) 1.16702(13) 0.46674(14) 0.0368(4) Uani 1 1 d . . . . .
H67A H 0.325398 1.191426 0.487957 0.055 Uiso 1 1 calc R U . . .
H67B H 0.216172 1.151377 0.513617 0.055 Uiso 1 1 calc R U . . .
H67C H 0.253335 1.214574 0.418664 0.055 Uiso 1 1 calc R U . . .
C70 C 0.00361(15) 1.18791(13) 0.26186(12) 0.0372(4) Uani 1 1 d . . . . .
H70A H 0.049247 1.224297 0.276245 0.056 Uiso 1 1 calc R U . . .
H70B H -0.059825 1.226674 0.253197 0.056 Uiso 1 1 calc R U . . .
H70C H 0.036547 1.167995 0.208706 0.056 Uiso 1 1 calc R U . . .
C11 C -0.03819(13) 0.68636(12) 0.44866(11) 0.0301(4) Uani 1 1 d . . . . .
H11A H -0.032386 0.745437 0.463777 0.036 Uiso 1 1 calc R U . . .
H11B H -0.079122 0.646041 0.499431 0.036 Uiso 1 1 calc R U . . .
C32 C 0.29453(12) 0.44040(12) -0.00948(11) 0.0277(3) Uani 1 1 d . . . . .
C36 C 0.21821(13) 0.29062(13) 0.06134(13) 0.0337(4) Uani 1 1 d . . . . .
H36 H 0.198529 0.242737 0.111605 0.040 Uiso 1 1 calc R U . . .
C9 C 0.10154(14) 0.58720(13) 0.50285(11) 0.0319(4) Uani 1 1 d . . . . .
H9A H 0.058643 0.535595 0.535002 0.038 Uiso 1 1 calc R U . . .
H9B H 0.099713 0.628953 0.541580 0.038 Uiso 1 1 calc R U . . .
C24 C 0.54248(12) 0.88929(12) 0.09391(10) 0.0267(3) Uani 1 1 d . . . . .
H24 H 0.597222 0.844588 0.080113 0.032 Uiso 1 1 calc R U . . .
C54 C -0.00546(14) 0.47740(12) 0.22071(12) 0.0313(4) Uani 1 1 d . . . . .
C1 C 0.26547(12) 0.36887(12) 0.06787(12) 0.0276(3) Uani 1 1 d . . . . .
C34 C 0.22909(15) 0.35520(14) -0.09390(14) 0.0393(4) Uani 1 1 d . . . . .
H34 H 0.216438 0.350430 -0.147315 0.047 Uiso 1 1 calc R U . . .
C71 C -0.09063(14) 1.04295(14) 0.31095(14) 0.0369(4) Uani 1 1 d . . . . .
H71A H -0.054985 1.023199 0.258312 0.055 Uiso 1 1 calc R U . . .
H71B H -0.153078 1.082241 0.300022 0.055 Uiso 1 1 calc R U . . .
H71C H -0.107983 0.987633 0.357710 0.055 Uiso 1 1 calc R U . . .
C73 C 0.37866(16) 0.70977(16) 0.66797(15) 0.0485(5) Uani 1 1 d . . . . .
H73 H 0.351663 0.776960 0.651964 0.058 Uiso 1 1 calc R U . . .
C75 C 0.3970(2) 0.6876(2) 0.76093(17) 0.0713(8) Uani 1 1 d . . . . .
H75A H 0.332036 0.695170 0.800910 0.107 Uiso 1 1 calc R U . . .
H75B H 0.443404 0.730494 0.764669 0.107 Uiso 1 1 calc R U . . .
H75C H 0.427184 0.622959 0.776439 0.107 Uiso 1 1 calc R U . . .
C74 C 0.30287(19) 0.64924(19) 0.6565(2) 0.0678(7) Uani 1 1 d . . . . .
H74A H 0.328312 0.583099 0.671855 0.102 Uiso 1 1 calc R U . . .
H74B H 0.294884 0.666355 0.596153 0.102 Uiso 1 1 calc R U . . .
H74C H 0.236873 0.659517 0.694278 0.102 Uiso 1 1 calc R U . . .
O76 O 0.47637(18) 0.7540(3) 0.44017(16) 0.0492(8) Uani 0.680(6) 1 d D U P A 1
H76 H 0.426882 0.758798 0.416174 0.074 Uiso 0.680(6) 1 calc R U P A 1
C77 C 0.5664(5) 0.7150(4) 0.3894(4) 0.0406(10) Uani 0.680(6) 1 d D U P A 1
H77 H 0.623401 0.706642 0.421056 0.049 Uiso 0.680(6) 1 calc R U P A 1
C79 C 0.5942(6) 0.7858(6) 0.3039(4) 0.089(2) Uani 0.680(6) 1 d D U P A 1
H79A H 0.537127 0.799048 0.273709 0.134 Uiso 0.680(6) 1 calc R U P A 1
H79B H 0.654375 0.760173 0.268035 0.134 Uiso 0.680(6) 1 calc R U P A 1
H79C H 0.609079 0.843738 0.314700 0.134 Uiso 0.680(6) 1 calc R U P A 1
C78 C 0.5513(4) 0.6197(4) 0.3788(5) 0.0908(18) Uani 0.680(6) 1 d D U P A 1
H78A H 0.531614 0.577835 0.435884 0.136 Uiso 0.680(6) 1 calc R U P A 1
H78B H 0.614971 0.593377 0.347729 0.136 Uiso 0.680(6) 1 calc R U P A 1
H78C H 0.497590 0.626496 0.345814 0.136 Uiso 0.680(6) 1 calc R U P A 1
C77A C 0.5658(12) 0.6944(11) 0.3764(10) 0.067(4) Uani 0.320(6) 1 d D U P A 2
H77A H 0.624871 0.665256 0.404367 0.081 Uiso 0.320(6) 1 calc R U P A 2
C78A C 0.5639(11) 0.6456(10) 0.3074(10) 0.109(4) Uani 0.320(6) 1 d D U P A 2
H78D H 0.502053 0.612834 0.322969 0.164 Uiso 0.320(6) 1 calc R U P A 2
H78E H 0.623851 0.600343 0.302003 0.164 Uiso 0.320(6) 1 calc R U P A 2
H78F H 0.564524 0.691782 0.252168 0.164 Uiso 0.320(6) 1 calc R U P A 2
C79A C 0.5801(12) 0.7976(10) 0.3367(9) 0.066(3) Uani 0.320(6) 1 d D U P A 2
H79D H 0.646362 0.803707 0.297032 0.098 Uiso 0.320(6) 1 calc R U P A 2
H79E H 0.577291 0.829515 0.382717 0.098 Uiso 0.320(6) 1 calc R U P A 2
H79F H 0.525892 0.826035 0.304819 0.098 Uiso 0.320(6) 1 calc R U P A 2
O76A O 0.4740(4) 0.6844(8) 0.4416(3) 0.068(3) Uani 0.320(6) 1 d D U P A 2
H76A H 0.424086 0.689316 0.418079 0.102 Uiso 0.320(6) 1 calc R U P A 2
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
C17 O16 C15 111.64(12) . . ?
C25 O26 C27 117.10(12) . . ?
C30 O29 C28 116.23(12) . . ?
C6 O7 C8 112.71(13) . . ?
C3 O4 C5 117.06(12) . . ?
C9 O10 C11 112.45(12) . . ?
C20 O19 C18 117.22(12) . . ?
C12 O13 C14 111.24(12) . . ?
C46 N47 H47 120.5 . . ?
C48 N47 H47 120.5 . . ?
C48 N47 C46 119.05(12) . . ?
C62 C61 H61 118.5 . . ?
C60 C61 H61 118.5 . . ?
C60 C61 C62 122.94(14) . . ?
C73 O72 H72 109.5 . . ?
C40 C41 H41 119.9 . . ?
C40 C41 C42 120.26(14) . . ?
C42 C41 H41 119.9 . . ?
C41 C40 C46 121.07(14) . . ?
C41 C40 C45 119.11(14) . . ?
C45 C40 C46 119.74(14) . . ?
C59 C58 C48 116.80(13) . . ?
C59 C58 C63 119.88(14) . . ?
C63 C58 C48 123.30(13) . . ?
N47 C46 C40 112.34(12) . . ?
N47 C46 H46A 109.1 . . ?
N47 C46 H46B 109.1 . . ?
C40 C46 H46A 109.1 . . ?
C40 C46 H46B 109.1 . . ?
H46A C46 H46B 107.9 . . ?
O49 C48 N47 120.42(14) . . ?
O49 C48 C58 120.81(13) . . ?
N47 C48 C58 118.74(13) . . ?
C41 C42 C43 120.91(14) . . ?
C41 C42 C50 120.21(14) . . ?
C43 C42 C50 118.87(14) . . ?
C22 C23 N37 118.94(15) . . ?
C22 C23 C24 122.79(15) . . ?
C24 C23 N37 118.27(16) . . ?
C43 C44 C45 120.77(15) . . ?
C43 C44 C54 120.11(14) . . ?
C45 C44 C54 119.10(15) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.42(16) . . ?
C58 C59 H59 119.3 . . ?
C58 C59 C60 121.39(14) . . ?
C60 C59 H59 119.3 . . ?
C42 C43 H43 120.7 . . ?
C44 C43 C42 118.59(14) . . ?
C44 C43 H43 120.7 . . ?
C61 C62 C68 119.16(13) . . ?
C63 C62 C61 117.88(14) . . ?
C63 C62 C68 122.94(14) . . ?
O29 C28 H28A 110.1 . . ?
O29 C28 H28B 110.1 . . ?
O29 C28 C27 107.86(13) . . ?
H28A C28 H28B 108.4 . . ?
C27 C28 H28A 110.1 . . ?
C27 C28 H28B 110.1 . . ?
C58 C63 H63 119.8 . . ?
C62 C63 C58 120.43(14) . . ?
C62 C63 H63 119.8 . . ?
O39 N37 O38 123.01(16) . . ?
O39 N37 C23 118.03(15) . . ?
O38 N37 C23 118.95(16) . . ?
H66A C66 H66B 109.5 . . ?
H66A C66 H66C 109.5 . . ?
H66B C66 H66C 109.5 . . ?
C64 C66 H66A 109.5 . . ?
C64 C66 H66B 109.5 . . ?
C64 C66 H66C 109.5 . . ?
O16 C17 H17A 109.7 . . ?
O16 C17 H17B 109.7 . . ?
O16 C17 C18 109.67(12) . . ?
H17A C17 H17B 108.2 . . ?
C18 C17 H17A 109.7 . . ?
C18 C17 H17B 109.7 . . ?
O13 C12 H12A 109.4 . . ?
O13 C12 H12B 109.4 . . ?
O13 C12 C11 110.96(13) . . ?
H12A C12 H12B 108.0 . . ?
C11 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
O26 C25 C20 114.90(13) . . ?
O26 C25 C24 125.20(14) . . ?
C24 C25 C20 119.89(14) . . ?
C40 C45 C44 120.35(14) . . ?
C40 C45 H45 119.8 . . ?
C44 C45 H45 119.8 . . ?
C61 C60 C59 117.42(14) . . ?
C61 C60 C64 123.20(14) . . ?
C59 C60 C64 119.38(14) . . ?
C3 C2 H2 119.4 . . ?
C3 C2 C1 121.13(15) . . ?
C1 C2 H2 119.4 . . ?
C30 C31 H31 119.4 . . ?
C30 C31 C32 121.16(15) . . ?
C32 C31 H31 119.4 . . ?
O19 C18 C17 107.94(12) . . ?
O19 C18 H18A 110.1 . . ?
O19 C18 H18B 110.1 . . ?
C17 C18 H18A 110.1 . . ?
C17 C18 H18B 110.1 . . ?
H18A C18 H18B 108.4 . . ?
C36 C35 H35 119.8 . . ?
C36 C35 C34 120.48(17) . . ?
C34 C35 H35 119.8 . . ?
O4 C5 H5A 109.9 . . ?
O4 C5 H5B 109.9 . . ?
O4 C5 C6 108.88(13) . . ?
H5A C5 H5B 108.3 . . ?
C6 C5 H5A 109.9 . . ?
C6 C5 H5B 109.9 . . ?
O16 C15 H15A 109.7 . . ?
O16 C15 H15B 109.7 . . ?
O16 C15 C14 109.69(13) . . ?
H15A C15 H15B 108.2 . . ?
C14 C15 H15A 109.7 . . ?
C14 C15 H15B 109.7 . . ?
O26 C27 C28 107.55(12) . . ?
O26 C27 H27A 110.2 . . ?
O26 C27 H27B 110.2 . . ?
C28 C27 H27A 110.2 . . ?
C28 C27 H27B 110.2 . . ?
H27A C27 H27B 108.5 . . ?
O7 C6 C5 108.64(14) . . ?
O7 C6 H6A 110.0 . . ?
O7 C6 H6B 110.0 . . ?
C5 C6 H6A 110.0 . . ?
C5 C6 H6B 110.0 . . ?
H6A C6 H6B 108.3 . . ?
C62 C68 C70 108.41(13) . . ?
C69 C68 C62 110.65(13) . . ?
C69 C68 C70 109.07(14) . . ?
C71 C68 C62 112.16(13) . . ?
C71 C68 C69 108.83(14) . . ?
C71 C68 C70 107.64(14) . . ?
C23 C22 C21 118.50(15) . . ?
C23 C22 H22 120.7 . . ?
C21 C22 H22 120.7 . . ?
O19 C20 C21 125.56(15) . . ?
O19 C20 C25 114.62(13) . . ?
C21 C20 C25 119.82(14) . . ?
O29 C30 C31 124.83(15) . . ?
O29 C30 C3 115.07(13) . . ?
C31 C30 C3 120.10(14) . . ?
H65A C65 H65B 109.5 . . ?
H65A C65 H65C 109.5 . . ?
H65B C65 H65C 109.5 . . ?
C64 C65 H65A 109.5 . . ?
C64 C65 H65B 109.5 . . ?
C64 C65 H65C 109.5 . . ?
O13 C14 C15 110.28(13) . . ?
O13 C14 H14A 109.6 . . ?
O13 C14 H14B 109.6 . . ?
C15 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C32 C33 H33 119.9 . . ?
C34 C33 H33 119.9 . . ?
C34 C33 C32 120.15(18) . . ?
O4 C3 C2 125.85(15) . . ?
O4 C3 C30 114.83(13) . . ?
C2 C3 C30 119.32(15) . . ?
F51 C50 F53 105.80(14) . . ?
F51 C50 F52 106.69(14) . . ?
F51 C50 C42 113.35(14) . . ?
F53 C50 C42 112.88(13) . . ?
F52 C50 F53 105.52(15) . . ?
F52 C50 C42 112.02(13) . . ?
C66 C64 C65 109.55(15) . . ?
C60 C64 C66 109.71(13) . . ?
C60 C64 C65 108.72(14) . . ?
C67 C64 C66 107.67(14) . . ?
C67 C64 C60 112.21(14) . . ?
C67 C64 C65 108.95(15) . . ?
C68 C69 H69A 109.5 . . ?
C68 C69 H69B 109.5 . . ?
C68 C69 H69C 109.5 . . ?
H69A C69 H69B 109.5 . . ?
H69A C69 H69C 109.5 . . ?
H69B C69 H69C 109.5 . . ?
O7 C8 H8A 109.9 . . ?
O7 C8 H8B 109.9 . . ?
O7 C8 C9 109.10(14) . . ?
H8A C8 H8B 108.3 . . ?
C9 C8 H8A 109.9 . . ?
C9 C8 H8B 109.9 . . ?
C64 C67 H67A 109.5 . . ?
C64 C67 H67B 109.5 . . ?
C64 C67 H67C 109.5 . . ?
H67A C67 H67B 109.5 . . ?
H67A C67 H67C 109.5 . . ?
H67B C67 H67C 109.5 . . ?
C68 C70 H70A 109.5 . . ?
C68 C70 H70B 109.5 . . ?
C68 C70 H70C 109.5 . . ?
H70A C70 H70B 109.5 . . ?
H70A C70 H70C 109.5 . . ?
H70B C70 H70C 109.5 . . ?
O10 C11 C12 109.53(13) . . ?
O10 C11 H11A 109.8 . . ?
O10 C11 H11B 109.8 . . ?
C12 C11 H11A 109.8 . . ?
C12 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
C31 C32 C33 121.77(16) . . ?
C1 C32 C31 118.88(15) . . ?
C1 C32 C33 119.35(15) . . ?
C35 C36 H36 119.6 . . ?
C35 C36 C1 120.79(17) . . ?
C1 C36 H36 119.6 . . ?
O10 C9 C8 109.21(13) . . ?
O10 C9 H9A 109.8 . . ?
O10 C9 H9B 109.8 . . ?
C8 C9 H9A 109.8 . . ?
C8 C9 H9B 109.8 . . ?
H9A C9 H9B 108.3 . . ?
C23 C24 H24 120.7 . . ?
C25 C24 C23 118.53(15) . . ?
C25 C24 H24 120.7 . . ?
F55 C54 F56 106.29(14) . . ?
F55 C54 F57 107.19(14) . . ?
F55 C54 C44 113.44(15) . . ?
F56 C54 C44 111.78(14) . . ?
F57 C54 F56 105.11(14) . . ?
F57 C54 C44 112.47(14) . . ?
C32 C1 C2 119.31(15) . . ?
C32 C1 C36 118.35(16) . . ?
C36 C1 C2 122.34(16) . . ?
C35 C34 H34 119.6 . . ?
C33 C34 C35 120.88(18) . . ?
C33 C34 H34 119.6 . . ?
C68 C71 H71A 109.5 . . ?
C68 C71 H71B 109.5 . . ?
C68 C71 H71C 109.5 . . ?
H71A C71 H71B 109.5 . . ?
H71A C71 H71C 109.5 . . ?
H71B C71 H71C 109.5 . . ?
O72 C73 H73 108.4 . . ?
O72 C73 C75 106.19(19) . . ?
O72 C73 C74 111.73(19) . . ?
C75 C73 H73 108.4 . . ?
C74 C73 H73 108.4 . . ?
C74 C73 C75 113.4(2) . . ?
C73 C75 H75A 109.5 . . ?
C73 C75 H75B 109.5 . . ?
C73 C75 H75C 109.5 . . ?
H75A C75 H75B 109.5 . . ?
H75A C75 H75C 109.5 . . ?
H75B C75 H75C 109.5 . . ?
C73 C74 H74A 109.5 . . ?
C73 C74 H74B 109.5 . . ?
C73 C74 H74C 109.5 . . ?
H74A C74 H74B 109.5 . . ?
H74A C74 H74C 109.5 . . ?
H74B C74 H74C 109.5 . . ?
C77 O76 H76 109.5 . . ?
O76 C77 H77 107.9 . . ?
O76 C77 C79 108.2(5) . . ?
O76 C77 C78 111.5(4) . . ?
C79 C77 H77 107.9 . . ?
C79 C77 C78 113.2(6) . . ?
C78 C77 H77 107.9 . . ?
C77 C79 H79A 109.5 . . ?
C77 C79 H79B 109.5 . . ?
C77 C79 H79C 109.5 . . ?
H79A C79 H79B 109.5 . . ?
H79A C79 H79C 109.5 . . ?
H79B C79 H79C 109.5 . . ?
C77 C78 H78A 109.5 . . ?
C77 C78 H78B 109.5 . . ?
C77 C78 H78C 109.5 . . ?
H78A C78 H78B 109.5 . . ?
H78A C78 H78C 109.5 . . ?
H78B C78 H78C 109.5 . . ?
C78A C77A H77A 108.4 . . ?
C78A C77A C79A 110.2(12) . . ?
C79A C77A H77A 108.4 . . ?
O76A C77A H77A 108.4 . . ?
O76A C77A C78A 111.0(12) . . ?
O76A C77A C79A 110.2(12) . . ?
C77A C78A H78D 109.5 . . ?
C77A C78A H78E 109.5 . . ?
C77A C78A H78F 109.5 . . ?
H78D C78A H78E 109.5 . . ?
H78D C78A H78F 109.5 . . ?
H78E C78A H78F 109.5 . . ?
C77A C79A H79D 109.5 . . ?
C77A C79A H79E 109.5 . . ?
C77A C79A H79F 109.5 . . ?
H79D C79A H79E 109.5 . . ?
H79D C79A H79F 109.5 . . ?
H79E C79A H79F 109.5 . . ?
C77A O76A H76A 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
O16 C17 1.4209(19) . ?
O16 C15 1.4276(18) . ?
F51 C50 1.3198(19) . ?
O26 C25 1.3618(18) . ?
O26 C27 1.4337(18) . ?
F55 C54 1.328(2) . ?
F56 C54 1.352(2) . ?
F57 C54 1.340(2) . ?
O29 C28 1.4328(19) . ?
O29 C30 1.3642(19) . ?
O7 C6 1.428(2) . ?
O7 C8 1.428(2) . ?
O4 C5 1.4376(19) . ?
O4 C3 1.3648(19) . ?
O10 C11 1.422(2) . ?
O10 C9 1.420(2) . ?
O19 C18 1.4363(18) . ?
O19 C20 1.3572(19) . ?
F53 C50 1.334(2) . ?
O49 C48 1.2420(19) . ?
F52 C50 1.332(2) . ?
O13 C12 1.422(2) . ?
O13 C14 1.4233(19) . ?
N47 H47 0.8600 . ?
N47 C46 1.4598(19) . ?
N47 C48 1.3317(19) . ?
C61 H61 0.9300 . ?
C61 C62 1.403(2) . ?
C61 C60 1.391(2) . ?
O39 N37 1.224(2) . ?
O72 H72 0.8200 . ?
O72 C73 1.418(2) . ?
C41 H41 0.9300 . ?
C41 C40 1.388(2) . ?
C41 C42 1.391(2) . ?
O38 N37 1.230(2) . ?
C40 C46 1.507(2) . ?
C40 C45 1.389(2) . ?
C58 C48 1.501(2) . ?
C58 C59 1.387(2) . ?
C58 C63 1.400(2) . ?
C46 H46A 0.9700 . ?
C46 H46B 0.9700 . ?
C42 C43 1.392(2) . ?
C42 C50 1.493(2) . ?
C23 N37 1.462(2) . ?
C23 C22 1.375(3) . ?
C23 C24 1.392(2) . ?
C44 C43 1.385(2) . ?
C44 C45 1.394(2) . ?
C44 C54 1.492(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.392(2) . ?
C21 C20 1.388(2) . ?
C59 H59 0.9300 . ?
C59 C60 1.396(2) . ?
C43 H43 0.9300 . ?
C62 C63 1.394(2) . ?
C62 C68 1.532(2) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 C27 1.498(2) . ?
C63 H63 0.9300 . ?
C66 H66A 0.9600 . ?
C66 H66B 0.9600 . ?
C66 H66C 0.9600 . ?
C66 C64 1.535(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.500(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.507(2) . ?
C25 C20 1.415(2) . ?
C25 C24 1.381(2) . ?
C45 H45 0.9300 . ?
C60 C64 1.534(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.369(2) . ?
C2 C1 1.425(2) . ?
C31 H31 0.9300 . ?
C31 C30 1.369(2) . ?
C31 C32 1.419(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C35 H35 0.9300 . ?
C35 C36 1.377(3) . ?
C35 C34 1.382(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.503(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C14 1.503(2) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C68 C69 1.531(2) . ?
C68 C70 1.532(2) . ?
C68 C71 1.523(2) . ?
C22 H22 0.9300 . ?
C30 C3 1.436(2) . ?
C65 H65A 0.9600 . ?
C65 H65B 0.9600 . ?
C65 H65C 0.9600 . ?
C65 C64 1.535(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C33 H33 0.9300 . ?
C33 C32 1.425(2) . ?
C33 C34 1.365(3) . ?
C64 C67 1.529(2) . ?
C69 H69A 0.9600 . ?
C69 H69B 0.9600 . ?
C69 H69C 0.9600 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.503(3) . ?
C67 H67A 0.9600 . ?
C67 H67B 0.9600 . ?
C67 H67C 0.9600 . ?
C70 H70A 0.9600 . ?
C70 H70B 0.9600 . ?
C70 H70C 0.9600 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C32 C1 1.411(2) . ?
C36 H36 0.9300 . ?
C36 C1 1.415(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C24 H24 0.9300 . ?
C34 H34 0.9300 . ?
C71 H71A 0.9600 . ?
C71 H71B 0.9600 . ?
C71 H71C 0.9600 . ?
C73 H73 0.9800 . ?
C73 C75 1.507(4) . ?
C73 C74 1.499(3) . ?
C75 H75A 0.9600 . ?
C75 H75B 0.9600 . ?
C75 H75C 0.9600 . ?
C74 H74A 0.9600 . ?
C74 H74B 0.9600 . ?
C74 H74C 0.9600 . ?
O76 H76 0.8200 . ?
O76 C77 1.417(6) . ?
C77 H77 0.9800 . ?
C77 C79 1.488(7) . ?
C77 C78 1.488(6) . ?
C79 H79A 0.9600 . ?
C79 H79B 0.9600 . ?
C79 H79C 0.9600 . ?
C78 H78A 0.9600 . ?
C78 H78B 0.9600 . ?
C78 H78C 0.9600 . ?
C77A H77A 0.9800 . ?
C77A C78A 1.467(14) . ?
C77A C79A 1.492(14) . ?
C77A O76A 1.410(13) . ?
C78A H78D 0.9600 . ?
C78A H78E 0.9600 . ?
C78A H78F 0.9600 . ?
C79A H79D 0.9600 . ?
C79A H79E 0.9600 . ?
C79A H79F 0.9600 . ?
O76A H76A 0.8200 . ?
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
O16 C17 C18 O19 69.51(16) . . . . ?
O16 C15 C14 O13 50.68(17) . . . . ?
O26 C25 C20 O19 -2.42(19) . . . . ?
O26 C25 C20 C21 178.15(14) . . . . ?
O26 C25 C24 C23 -179.42(14) . . . . ?
O29 C28 C27 O26 -81.78(15) . . . . ?
O29 C30 C3 O4 4.00(19) . . . . ?
O29 C30 C3 C2 -176.77(14) . . . . ?
O7 C8 C9 O10 -55.84(18) . . . . ?
O4 C5 C6 O7 88.94(16) . . . . ?
O13 C12 C11 O10 -76.59(17) . . . . ?
C61 C62 C63 C58 -2.1(2) . . . . ?
C61 C62 C68 C69 -53.49(19) . . . . ?
C61 C62 C68 C70 66.07(18) . . . . ?
C61 C62 C68 C71 -175.21(15) . . . . ?
C61 C60 C64 C66 128.62(16) . . . . ?
C61 C60 C64 C65 -111.60(18) . . . . ?
C61 C60 C64 C67 9.0(2) . . . . ?
C41 C40 C46 N47 73.56(18) . . . . ?
C41 C40 C45 C44 1.0(2) . . . . ?
C41 C42 C43 C44 0.6(2) . . . . ?
C41 C42 C50 F51 142.11(15) . . . . ?
C41 C42 C50 F53 21.8(2) . . . . ?
C41 C42 C50 F52 -97.09(18) . . . . ?
C40 C41 C42 C43 0.1(2) . . . . ?
C40 C41 C42 C50 179.46(14) . . . . ?
C58 C59 C60 C61 -1.9(2) . . . . ?
C58 C59 C60 C64 178.95(14) . . . . ?
C46 N47 C48 O49 -0.1(2) . . . . ?
C46 N47 C48 C58 177.98(13) . . . . ?
C46 C40 C45 C44 -175.77(14) . . . . ?
C48 N47 C46 C40 174.85(13) . . . . ?
C48 C58 C59 C60 178.38(14) . . . . ?
C48 C58 C63 C62 -176.24(14) . . . . ?
C42 C41 C40 C46 175.80(13) . . . . ?
C42 C41 C40 C45 -0.9(2) . . . . ?
C59 C58 C48 O49 17.4(2) . . . . ?
C59 C58 C48 N47 -160.74(14) . . . . ?
C59 C58 C63 C62 2.3(2) . . . . ?
C59 C60 C64 C66 -52.2(2) . . . . ?
C59 C60 C64 C65 67.54(19) . . . . ?
C59 C60 C64 C67 -171.88(15) . . . . ?
C43 C42 C50 F51 -38.5(2) . . . . ?
C43 C42 C50 F53 -158.80(15) . . . . ?
C43 C42 C50 F52 82.26(19) . . . . ?
C43 C44 C45 C40 -0.3(2) . . . . ?
C43 C44 C54 F55 24.2(2) . . . . ?
C43 C44 C54 F56 -95.92(18) . . . . ?
C43 C44 C54 F57 146.10(15) . . . . ?
C62 C61 C60 C59 2.0(2) . . . . ?
C62 C61 C60 C64 -178.81(15) . . . . ?
C28 O29 C30 C31 -5.7(2) . . . . ?
C28 O29 C30 C3 174.01(13) . . . . ?
C63 C58 C48 O49 -164.07(15) . . . . ?
C63 C58 C48 N47 17.8(2) . . . . ?
C63 C58 C59 C60 -0.2(2) . . . . ?
C63 C62 C68 C69 128.32(16) . . . . ?
C63 C62 C68 C70 -112.12(17) . . . . ?
C63 C62 C68 C71 6.6(2) . . . . ?
N37 C23 C22 C21 179.40(15) . . . . ?
N37 C23 C24 C25 179.81(14) . . . . ?
C17 O16 C15 C14 171.97(13) . . . . ?
C12 O13 C14 C15 171.23(13) . . . . ?
C25 O26 C27 C28 179.29(13) . . . . ?
C45 C40 C46 N47 -109.77(16) . . . . ?
C45 C44 C43 C42 -0.5(2) . . . . ?
C45 C44 C54 F55 -157.49(15) . . . . ?
C45 C44 C54 F56 82.35(19) . . . . ?
C45 C44 C54 F57 -35.6(2) . . . . ?
C60 C61 C62 C63 -0.1(2) . . . . ?
C60 C61 C62 C68 -178.36(14) . . . . ?
C31 C30 C3 O4 -176.30(14) . . . . ?
C31 C30 C3 C2 2.9(2) . . . . ?
C31 C32 C1 C2 1.3(2) . . . . ?
C31 C32 C1 C36 -179.44(15) . . . . ?
C18 O19 C20 C21 3.7(2) . . . . ?
C18 O19 C20 C25 -175.68(13) . . . . ?
C35 C36 C1 C2 179.23(16) . . . . ?
C35 C36 C1 C32 0.0(2) . . . . ?
C5 O4 C3 C2 3.8(2) . . . . ?
C5 O4 C3 C30 -177.03(13) . . . . ?
C15 O16 C17 C18 161.65(13) . . . . ?
C27 O26 C25 C20 176.35(13) . . . . ?
C27 O26 C25 C24 -2.8(2) . . . . ?
C6 O7 C8 C9 -176.52(13) . . . . ?
C68 C62 C63 C58 176.12(14) . . . . ?
C22 C23 N37 O39 -176.54(16) . . . . ?
C22 C23 N37 O38 4.0(2) . . . . ?
C22 C23 C24 C25 0.5(2) . . . . ?
C22 C21 C20 O19 -177.46(15) . . . . ?
C22 C21 C20 C25 1.9(2) . . . . ?
C20 O19 C18 C17 -177.82(13) . . . . ?
C20 C21 C22 C23 0.0(2) . . . . ?
C20 C25 C24 C23 1.5(2) . . . . ?
C30 O29 C28 C27 -178.90(12) . . . . ?
C30 C31 C32 C33 178.44(16) . . . . ?
C30 C31 C32 C1 -1.9(2) . . . . ?
C14 O13 C12 C11 163.48(13) . . . . ?
C33 C32 C1 C2 -179.00(15) . . . . ?
C33 C32 C1 C36 0.3(2) . . . . ?
C3 O4 C5 C6 -168.88(13) . . . . ?
C3 C2 C1 C32 1.4(2) . . . . ?
C3 C2 C1 C36 -177.82(16) . . . . ?
C50 C42 C43 C44 -178.77(14) . . . . ?
C8 O7 C6 C5 -169.29(13) . . . . ?
C11 O10 C9 C8 -174.83(14) . . . . ?
C32 C31 C30 O29 179.43(14) . . . . ?
C32 C31 C30 C3 -0.2(2) . . . . ?
C32 C33 C34 C35 -0.3(3) . . . . ?
C36 C35 C34 C33 0.6(3) . . . . ?
C9 O10 C11 C12 -158.69(14) . . . . ?
C24 C23 N37 O39 4.1(2) . . . . ?
C24 C23 N37 O38 -175.40(17) . . . . ?
C24 C23 C22 C21 -1.3(2) . . . . ?
C24 C25 C20 O19 176.74(14) . . . . ?
C24 C25 C20 C21 -2.7(2) . . . . ?
C54 C44 C43 C42 177.73(15) . . . . ?
C54 C44 C45 C40 -178.52(14) . . . . ?
C1 C2 C3 O4 175.63(14) . . . . ?
C1 C2 C3 C30 -3.5(2) . . . . ?
C34 C35 C36 C1 -0.4(3) . . . . ?
C34 C33 C32 C31 179.60(17) . . . . ?
C34 C33 C32 C1 -0.1(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168336437
