#------------------------------------------------------------------------------
#$Date: 2024-01-06 11:46:15 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288901 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/96/7159617.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_7159617
loop_
_publ_author_name
'Zelentsova, Maria V.'
'Sandulenko, Irina V.'
'Ambartsumyan, Asmik A.'
'Danshina, Anastasia A.'
'Moiseev, Sergey K.'
_publ_section_title
;
 C(21)-Di- and monofluorinated scaffold for thevinol/orvinol-based opioid
 receptor ligands.
;
_journal_issue                   45
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              9091
_journal_page_last               9100
_journal_paper_doi               10.1039/d3ob01577g
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C23 H26 F2 N2 O4'
_chemical_formula_sum            'C23 H26 F2 N2 O4'
_chemical_formula_weight         432.46
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2023-09-12
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-09-12 deposited with the CCDC.	2023-10-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7726(4)
_cell_length_b                   11.5067(6)
_cell_length_c                   22.6755(10)
_cell_measurement_reflns_used    5815
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.47
_cell_measurement_theta_min      2.52
_cell_volume                     2028.03(17)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker Quest D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0914
_diffrn_reflns_av_unetI/netI     0.0735
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            26533
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.998
_diffrn_reflns_theta_min         1.985
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_correction_T_min  0.7309
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1535 before and 0.0828 after correction.
The Ratio of minimum to maximum transmission is 0.8477.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_description       needle
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 1518 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         5347
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0673
_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)+(0.0528P)²+1.8343P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1487
_refine_ls_wR_factor_ref         0.1573
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                4287
_reflns_number_total             5347
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01577g2.cif
_cod_data_source_block           40
_cod_depositor_comments
'Adding full bibliography for 7159615--7159624.cif.'
_cod_database_code               7159617
_shelxl_version_number           2014/6
_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   0.996
_shelx_estimated_absorpt_t_min   0.979
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-C17 \\sim N1-C17'
 with sigma of 0.02
 N2-C17 \\sim N2'-C17'
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(N2) = Uanis(N2')
Uanis(C17) = Uanis(C17')
4. Others
 Sof(N2')=Sof(C17')=1-FVAR(1)
 Sof(N2)=Sof(C17)=FVAR(1)
5.a Riding coordinates:
 O4(H4)
5.b Ternary CH refined with riding coordinates:
 C5(H5), C7(H7), C9(H9), C20(H20), C21(H21)
5.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C15(H15A,H15B), C16(H16A,H16B), C18(H18A,H18B),
 C19(H19A,H19B)
5.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2)
5.e Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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
F1 F 0.7721(4) 0.4605(3) 0.27189(14) 0.0520(10) Uani 1 1 d . . . . .
F2 F 0.7082(5) 0.3100(4) 0.21807(14) 0.0570(11) Uani 1 1 d . . . . .
O1 O 0.4893(4) 0.4575(3) 0.61907(13) 0.0279(7) Uani 1 1 d . . . . .
O2 O 0.5286(3) 0.5035(2) 0.49811(12) 0.0161(6) Uani 1 1 d . . . . .
O3 O 0.6665(3) 0.3668(2) 0.39529(13) 0.0182(6) Uani 1 1 d . . . . .
O4 O 0.4180(5) 0.2669(3) 0.28984(15) 0.0312(8) Uani 1 1 d . . . . .
H4 H 0.3340 0.2617 0.2563 0.037 Uiso 1 1 d R U . . .
N1 N 0.0256(5) 0.6817(3) 0.37424(17) 0.0226(8) Uani 1 1 d D . . . .
C1 C 0.0451(6) 0.5297(3) 0.56934(19) 0.0228(9) Uani 1 1 d . . . . .
H1 H -0.0696 0.5279 0.5837 0.027 Uiso 1 1 calc R U . . .
C2 C 0.1802(6) 0.5031(4) 0.60760(19) 0.0235(9) Uani 1 1 d . . . . .
H2 H 0.1565 0.4902 0.6482 0.028 Uiso 1 1 calc R U . . .
C3 C 0.3502(6) 0.4950(3) 0.58733(18) 0.0201(8) Uani 1 1 d . . . . .
C4 C 0.3774(5) 0.5225(3) 0.52880(17) 0.0164(8) Uani 1 1 d . . . . .
C5 C 0.4913(5) 0.5236(3) 0.43530(17) 0.0146(7) Uani 1 1 d . . . . .
H5 H 0.5759 0.5807 0.4191 0.018 Uiso 1 1 calc R U . . .
C6 C 0.4950(5) 0.4127(3) 0.39760(18) 0.0147(7) Uani 1 1 d . . . . .
C7 C 0.4547(5) 0.4586(3) 0.33482(17) 0.0176(8) Uani 1 1 d . . . . .
H7 H 0.5263 0.5299 0.3290 0.021 Uiso 1 1 calc R U . . .
C8 C 0.2626(5) 0.4973(4) 0.33033(18) 0.0194(8) Uani 1 1 d . . . . .
H8A H 0.2549 0.5745 0.3112 0.023 Uiso 1 1 calc R U . . .
H8B H 0.1968 0.4410 0.3063 0.023 Uiso 1 1 calc R U . . .
C9 C 0.0090(5) 0.5615(3) 0.39846(19) 0.0204(8) Uani 1 1 d . . . . .
H9 H -0.0751 0.5174 0.3737 0.025 Uiso 1 1 calc R U . . .
C10 C -0.0597(5) 0.5665(4) 0.4628(2) 0.0218(9) Uani 1 1 d . . . . .
H10A H -0.1239 0.6401 0.4679 0.026 Uiso 1 1 calc R U . . .
H10B H -0.1425 0.5020 0.4684 0.026 Uiso 1 1 calc R U . . .
C11 C 0.0746(5) 0.5589(3) 0.51078(18) 0.0176(8) Uani 1 1 d . . . . .
C12 C 0.2467(5) 0.5618(3) 0.49382(18) 0.0165(8) Uani 1 1 d . . . . .
C13 C 0.3083(5) 0.5762(3) 0.43200(17) 0.0142(7) Uani 1 1 d . . . . .
C14 C 0.1874(5) 0.5033(3) 0.39279(17) 0.0160(7) Uani 1 1 d . . . . .
C15 C 0.1409(6) 0.7607(4) 0.40761(19) 0.0215(9) Uani 1 1 d . . . . .
H15A H 0.0937 0.7748 0.4475 0.026 Uiso 1 1 calc R U . . .
H15B H 0.1506 0.8363 0.3870 0.026 Uiso 1 1 calc R U . . .
C16 C 0.3162(5) 0.7036(3) 0.41206(18) 0.0177(8) Uani 1 1 d . . . . .
H16A H 0.3876 0.7479 0.4404 0.021 Uiso 1 1 calc R U . . .
H16B H 0.3732 0.7075 0.3731 0.021 Uiso 1 1 calc R U . . .
C18 C 0.3620(5) 0.3260(3) 0.41987(18) 0.0161(7) Uani 1 1 d . . . . .
H18A H 0.3857 0.3072 0.4617 0.019 Uiso 1 1 calc R U . . .
H18B H 0.3702 0.2532 0.3968 0.019 Uiso 1 1 calc R U . . .
C19 C 0.1795(5) 0.3765(3) 0.41415(18) 0.0166(8) Uani 1 1 d . . . . .
H19A H 0.1122 0.3295 0.3858 0.020 Uiso 1 1 calc R U . . .
H19B H 0.1208 0.3731 0.4529 0.020 Uiso 1 1 calc R U . . .
C20 C 0.4962(6) 0.3764(4) 0.28337(19) 0.0227(9) Uani 1 1 d . . . . .
H20 H 0.4477 0.4124 0.2468 0.027 Uiso 1 1 calc R U . . .
C21 C 0.6857(7) 0.3580(5) 0.2728(2) 0.0347(12) Uani 1 1 d . . . . .
H21 H 0.7347 0.3058 0.3038 0.042 Uiso 1 1 calc R U . . .
C22 C 0.4594(8) 0.4286(5) 0.6796(2) 0.0418(14) Uani 1 1 d . . . . .
H22A H 0.3735 0.3664 0.6820 0.063 Uiso 1 1 calc R U . . .
H22B H 0.4171 0.4973 0.7007 0.063 Uiso 1 1 calc R U . . .
H22C H 0.5671 0.4022 0.6977 0.063 Uiso 1 1 calc R U . . .
C23 C 0.7163(5) 0.2917(4) 0.4426(2) 0.0217(9) Uani 1 1 d . . . . .
H23A H 0.8374 0.2697 0.4378 0.033 Uiso 1 1 calc R U . . .
H23B H 0.6445 0.2217 0.4421 0.033 Uiso 1 1 calc R U . . .
H23C H 0.7013 0.3322 0.4802 0.033 Uiso 1 1 calc R U . . .
N2 N -0.212(3) 0.7515(11) 0.3116(11) 0.051(5) Uani 0.74(6) 1 d D . P A 1
C17 C -0.100(3) 0.719(3) 0.3410(10) 0.031(4) Uani 0.74(6) 1 d D . P A 1
N2' N -0.154(7) 0.754(4) 0.2948(19) 0.051(5) Uani 0.26(6) 1 d D . P A 2
C17' C -0.071(8) 0.727(8) 0.334(3) 0.031(4) Uani 0.26(6) 1 d D . 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 0.0033 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
C3 O1 C22 116.7(4) . . ?
C4 O2 C5 107.1(3) . . ?
C23 O3 C6 116.5(3) . . ?
C20 O4 H4 104.8 . . ?
C15 N1 C9 115.6(3) . . ?
C17 N1 C9 116.7(14) . . ?
C17 N1 C15 123.1(15) . . ?
C17' N1 C9 126(4) . . ?
C17' N1 C15 118(5) . . ?
C2 C1 H1 119.2 . . ?
C11 C1 H1 119.2 . . ?
C11 C1 C2 121.5(4) . . ?
C1 C2 H2 119.4 . . ?
C1 C2 C3 121.3(4) . . ?
C3 C2 H2 119.4 . . ?
O1 C3 C2 126.4(4) . . ?
O1 C3 C4 117.2(4) . . ?
C4 C3 C2 116.4(4) . . ?
C3 C4 O2 125.3(4) . . ?
C12 C4 O2 113.1(3) . . ?
C12 C4 C3 121.3(4) . . ?
O2 C5 H5 109.2 . . ?
O2 C5 C6 113.9(3) . . ?
O2 C5 C13 106.8(3) . . ?
C6 C5 H5 109.2 . . ?
C6 C5 C13 108.4(3) . . ?
C13 C5 H5 109.2 . . ?
O3 C6 C5 110.1(3) . . ?
O3 C6 C7 106.2(3) . . ?
O3 C6 C18 113.7(3) . . ?
C5 C6 C7 103.0(3) . . ?
C18 C6 C5 110.3(3) . . ?
C18 C6 C7 113.0(3) . . ?
C6 C7 H7 106.8 . . ?
C6 C7 C8 110.5(3) . . ?
C8 C7 H7 106.8 . . ?
C20 C7 C6 116.4(3) . . ?
C20 C7 H7 106.8 . . ?
C20 C7 C8 109.1(3) . . ?
C7 C8 H8A 110.0 . . ?
C7 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
C14 C8 C7 108.5(3) . . ?
C14 C8 H8A 110.0 . . ?
C14 C8 H8B 110.0 . . ?
N1 C9 H9 108.7 . . ?
N1 C9 C10 109.9(3) . . ?
N1 C9 C14 107.1(3) . . ?
C10 C9 H9 108.7 . . ?
C14 C9 H9 108.7 . . ?
C14 C9 C10 113.7(3) . . ?
C9 C10 H10A 108.3 . . ?
C9 C10 H10B 108.3 . . ?
H10A C10 H10B 107.4 . . ?
C11 C10 C9 115.8(3) . . ?
C11 C10 H10A 108.3 . . ?
C11 C10 H10B 108.3 . . ?
C1 C11 C10 126.0(4) . . ?
C1 C11 C12 115.4(4) . . ?
C12 C11 C10 117.7(4) . . ?
C4 C12 C11 123.1(4) . . ?
C4 C12 C13 110.1(3) . . ?
C11 C12 C13 124.8(4) . . ?
C12 C13 C5 101.9(3) . . ?
C12 C13 C14 106.6(3) . . ?
C12 C13 C16 113.3(3) . . ?
C14 C13 C5 112.0(3) . . ?
C16 C13 C5 110.6(3) . . ?
C16 C13 C14 112.0(3) . . ?
C8 C14 C9 116.0(3) . . ?
C8 C14 C13 108.9(3) . . ?
C8 C14 C19 105.3(3) . . ?
C13 C14 C9 105.2(3) . . ?
C19 C14 C9 110.4(3) . . ?
C19 C14 C13 111.0(3) . . ?
N1 C15 H15A 110.1 . . ?
N1 C15 H15B 110.1 . . ?
N1 C15 C16 108.1(3) . . ?
H15A C15 H15B 108.4 . . ?
C16 C15 H15A 110.1 . . ?
C16 C15 H15B 110.1 . . ?
C13 C16 H16A 108.9 . . ?
C13 C16 H16B 108.9 . . ?
C15 C16 C13 113.4(3) . . ?
C15 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C6 C18 H18A 109.6 . . ?
C6 C18 H18B 109.6 . . ?
C6 C18 C19 110.5(3) . . ?
H18A C18 H18B 108.1 . . ?
C19 C18 H18A 109.6 . . ?
C19 C18 H18B 109.6 . . ?
C14 C19 C18 110.4(3) . . ?
C14 C19 H19A 109.6 . . ?
C14 C19 H19B 109.6 . . ?
C18 C19 H19A 109.6 . . ?
C18 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
O4 C20 C7 112.4(3) . . ?
O4 C20 H20 107.2 . . ?
O4 C20 C21 108.3(4) . . ?
C7 C20 H20 107.2 . . ?
C21 C20 C7 114.3(4) . . ?
C21 C20 H20 107.2 . . ?
F1 C21 F2 105.8(4) . . ?
F1 C21 C20 111.4(4) . . ?
F1 C21 H21 110.2 . . ?
F2 C21 C20 109.0(4) . . ?
F2 C21 H21 110.2 . . ?
C20 C21 H21 110.2 . . ?
O1 C22 H22A 109.5 . . ?
O1 C22 H22B 109.5 . . ?
O1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N2 C17 N1 180(3) . . ?
N2' C17' N1 172(10) . . ?
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 C21 1.357(6) . ?
F2 C21 1.370(5) . ?
O1 C3 1.369(5) . ?
O1 C22 1.432(6) . ?
O2 C4 1.383(5) . ?
O2 C5 1.472(5) . ?
O3 C6 1.434(5) . ?
O3 C23 1.430(5) . ?
O4 H4 1.0041 . ?
O4 C20 1.406(5) . ?
N1 C9 1.494(5) . ?
N1 C15 1.483(5) . ?
N1 C17 1.305(9) . ?
N1 C17' 1.29(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.396(6) . ?
C1 C11 1.389(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.402(6) . ?
C3 C4 1.381(5) . ?
C4 C12 1.366(6) . ?
C5 H5 1.0000 . ?
C5 C6 1.536(5) . ?
C5 C13 1.547(5) . ?
C6 C7 1.550(6) . ?
C6 C18 1.523(5) . ?
C7 H7 1.0000 . ?
C7 C8 1.562(6) . ?
C7 C20 1.536(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C14 1.533(6) . ?
C9 H9 1.0000 . ?
C9 C10 1.556(6) . ?
C9 C14 1.545(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.510(6) . ?
C11 C12 1.392(5) . ?
C12 C13 1.491(5) . ?
C13 C14 1.542(5) . ?
C13 C16 1.536(5) . ?
C14 C19 1.538(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.516(6) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.539(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20 1.0000 . ?
C20 C21 1.507(7) . ?
C21 H21 1.0000 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
N2 C17 1.156(10) . ?
N2' C17' 1.14(2) . ?
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 C3 C4 O2 7.4(6) . . . . ?
O1 C3 C4 C12 -179.3(3) . . . . ?
O2 C4 C12 C11 163.1(4) . . . . ?
O2 C4 C12 C13 -1.6(4) . . . . ?
O2 C5 C6 O3 -66.4(4) . . . . ?
O2 C5 C6 C7 -179.3(3) . . . . ?
O2 C5 C6 C18 59.9(4) . . . . ?
O2 C5 C13 C12 -9.4(4) . . . . ?
O2 C5 C13 C14 -123.1(3) . . . . ?
O2 C5 C13 C16 111.3(3) . . . . ?
O3 C6 C7 C8 173.3(3) . . . . ?
O3 C6 C7 C20 48.2(4) . . . . ?
O3 C6 C18 C19 -173.3(3) . . . . ?
O4 C20 C21 F1 -174.0(4) . . . . ?
O4 C20 C21 F2 69.6(5) . . . . ?
N1 C9 C10 C11 -97.5(4) . . . . ?
N1 C9 C14 C8 -57.7(4) . . . . ?
N1 C9 C14 C13 62.8(4) . . . . ?
N1 C9 C14 C19 -177.3(3) . . . . ?
N1 C15 C16 C13 -48.1(5) . . . . ?
C1 C2 C3 O1 -172.5(4) . . . . ?
C1 C2 C3 C4 4.3(6) . . . . ?
C1 C11 C12 C4 9.5(6) . . . . ?
C1 C11 C12 C13 171.9(4) . . . . ?
C2 C1 C11 C10 167.4(4) . . . . ?
C2 C1 C11 C12 -1.3(6) . . . . ?
C2 C3 C4 O2 -169.7(3) . . . . ?
C2 C3 C4 C12 3.7(6) . . . . ?
C3 C4 C12 C11 -11.0(6) . . . . ?
C3 C4 C12 C13 -175.7(3) . . . . ?
C4 O2 C5 C6 -110.6(3) . . . . ?
C4 O2 C5 C13 8.9(4) . . . . ?
C4 C12 C13 C5 6.9(4) . . . . ?
C4 C12 C13 C14 124.5(3) . . . . ?
C4 C12 C13 C16 -111.9(4) . . . . ?
C5 O2 C4 C3 169.0(4) . . . . ?
C5 O2 C4 C12 -4.8(4) . . . . ?
C5 C6 C7 C8 -71.0(4) . . . . ?
C5 C6 C7 C20 163.9(3) . . . . ?
C5 C6 C18 C19 62.5(4) . . . . ?
C5 C13 C14 C8 -59.5(4) . . . . ?
C5 C13 C14 C9 175.5(3) . . . . ?
C5 C13 C14 C19 56.0(4) . . . . ?
C5 C13 C16 C15 179.8(3) . . . . ?
C6 C5 C13 C12 113.7(3) . . . . ?
C6 C5 C13 C14 0.0(4) . . . . ?
C6 C5 C13 C16 -125.6(3) . . . . ?
C6 C7 C8 C14 12.7(4) . . . . ?
C6 C7 C20 O4 54.2(5) . . . . ?
C6 C7 C20 C21 -69.7(5) . . . . ?
C6 C18 C19 C14 -5.0(5) . . . . ?
C7 C6 C18 C19 -52.1(4) . . . . ?
C7 C8 C14 C9 169.2(3) . . . . ?
C7 C8 C14 C13 50.7(4) . . . . ?
C7 C8 C14 C19 -68.4(4) . . . . ?
C7 C20 C21 F1 -47.9(6) . . . . ?
C7 C20 C21 F2 -164.2(4) . . . . ?
C8 C7 C20 O4 -71.6(4) . . . . ?
C8 C7 C20 C21 164.4(4) . . . . ?
C8 C14 C19 C18 65.0(4) . . . . ?
C9 N1 C15 C16 55.7(5) . . . . ?
C9 C10 C11 C1 -161.1(4) . . . . ?
C9 C10 C11 C12 7.3(5) . . . . ?
C9 C14 C19 C18 -169.1(3) . . . . ?
C10 C9 C14 C8 -179.2(3) . . . . ?
C10 C9 C14 C13 -58.8(4) . . . . ?
C10 C9 C14 C19 61.1(4) . . . . ?
C10 C11 C12 C4 -160.2(4) . . . . ?
C10 C11 C12 C13 2.2(6) . . . . ?
C11 C1 C2 C3 -5.5(6) . . . . ?
C11 C12 C13 C5 -157.5(4) . . . . ?
C11 C12 C13 C14 -39.9(5) . . . . ?
C11 C12 C13 C16 83.7(5) . . . . ?
C12 C13 C14 C8 -170.2(3) . . . . ?
C12 C13 C14 C9 64.8(4) . . . . ?
C12 C13 C14 C19 -54.7(4) . . . . ?
C12 C13 C16 C15 -66.5(4) . . . . ?
C13 C5 C6 O3 174.9(3) . . . . ?
C13 C5 C6 C7 62.0(4) . . . . ?
C13 C5 C6 C18 -58.8(4) . . . . ?
C13 C14 C19 C18 -52.8(4) . . . . ?
C14 C9 C10 C11 22.5(5) . . . . ?
C14 C13 C16 C15 54.1(5) . . . . ?
C15 N1 C9 C10 58.7(4) . . . . ?
C15 N1 C9 C14 -65.3(4) . . . . ?
C16 C13 C14 C8 65.3(4) . . . . ?
C16 C13 C14 C9 -59.7(4) . . . . ?
C16 C13 C14 C19 -179.1(3) . . . . ?
C18 C6 C7 C8 48.0(4) . . . . ?
C18 C6 C7 C20 -77.1(4) . . . . ?
C20 C7 C8 C14 141.9(3) . . . . ?
C22 O1 C3 C2 -3.0(6) . . . . ?
C22 O1 C3 C4 -179.7(4) . . . . ?
C23 O3 C6 C5 85.7(4) . . . . ?
C23 O3 C6 C7 -163.6(3) . . . . ?
C23 O3 C6 C18 -38.6(5) . . . . ?
C17 N1 C9 C10 -98.2(16) . . . . ?
C17 N1 C9 C14 137.9(15) . . . . ?
C17 N1 C15 C16 -149.1(15) . . . . ?
C17' N1 C9 C10 -109(5) . . . . ?
C17' N1 C9 C14 127(5) . . . . ?
C17' N1 C15 C16 -135(4) . . . . ?
