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#$Date: 2024-01-06 11:46:15 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288901 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/96/7159621.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_7159621
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         'C24 H31 F2 N O4, H2 O, C2 H6 O'
_chemical_formula_sum            'C26 H39 F2 N O6'
_chemical_formula_weight         499.58
_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             2023-08-31
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-09-11 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                   9.5587(9)
_cell_length_b                   10.1828(8)
_cell_length_c                   24.801(2)
_cell_measurement_reflns_used    9876
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.66
_cell_measurement_theta_min      2.16
_cell_volume                     2414.0(4)
_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
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Quest D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1520
_diffrn_reflns_av_unetI/netI     0.0659
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            59479
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.997
_diffrn_reflns_theta_min         1.642
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1368 before and 0.0797 after correction.
The Ratio of minimum to maximum transmission is 0.8035.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_description       needle
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.608
_refine_diff_density_rms         0.116
_refine_ls_abs_structure_details
;
 Flack x determined using 1821 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.33(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         5837
_refine_ls_number_restraints     101
_refine_ls_restrained_S_all      1.146
_refine_ls_R_factor_all          0.1132
_refine_ls_R_factor_gt           0.0982
_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)+14.5778P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2223
_refine_ls_wR_factor_ref         0.2272
_reflns_Friedel_coverage         0.766
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4932
_reflns_number_total             5837
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01577g2.cif
_cod_data_source_block           38
_cod_depositor_comments
'Adding full bibliography for 7159615--7159624.cif.'
_cod_database_code               7159621
_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   0.999
_shelx_estimated_absorpt_t_min   0.989
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups, All O(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1S-C1S \\sim O1S-C1'S
 with sigma of 0.02
 O1S-C1S \\sim O1'S-C1'S
 with sigma of 0.02
 O1'S-H1'S \\sim O1S-H1S
 with sigma of 0.02
 C2S-C1S \\sim C2'S-C1'S
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C19) \\sim Ueq, Uanis(C24) \\sim Ueq: with sigma of 0.05 and sigma for
terminal atoms of 0.1
Uanis(O1S) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(O1) \\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(C24)
\\sim Ueq, Uanis(C19) \\sim Ueq: with sigma of 0.005 and sigma for terminal
atoms of 0.01
Uanis(C22) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C1) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
Uanis(C1S) \\sim Ueq, Uanis(C1'S) \\sim Ueq, Uanis(C2'S) \\sim Ueq, Uanis(C2S)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C12) \\sim Ueq, Uanis(C4) \\sim Ueq: with sigma of 0.05 and sigma for
terminal atoms of 0.1
Uanis(C4) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
Uanis(O1S) = Uanis(O1'S)
Uanis(C1'S) = Uanis(C1S)
Uanis(C2'S) = Uanis(C2S)
4. Others
 Sof(O1S)=Sof(H1S)=Sof(C1S)=Sof(H1SA)=Sof(H1SB)=Sof(C2S)=Sof(H2SA)=Sof(H2SB)=
 Sof(H2SC)=1-FVAR(1)
 Sof(O1'S)=Sof(H1'S)=Sof(C1'S)=Sof(H1'A)=Sof(H1'B)=Sof(C2'S)=Sof(H2'A)=
 Sof(H2'B)=Sof(H2'C)=FVAR(1)
5.a Riding coordinates:
 O4(H4), O2S(H2SD,H2SE), O1S(H1S), O1'S(H1'S)
5.b Ternary CH refined with riding coordinates:
 C5(H5), C7(H7), C9(H9), C22(H22)
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), C1S(H1SA,H1SB), C1'S(H1'A,H1'B)
5.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2)
5.e Idealised Me refined as rotating group:
 C17(H17A,H17C,H17B), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C2S(H2SA,H2SB,H2SC), C2'S(H2'A,H2'B,H2'C)
;
_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 0.1700(6) 0.5556(5) 0.56768(17) 0.0320(12) Uani 1 1 d . . . . .
F2 F 0.1339(5) 0.3489(5) 0.58598(16) 0.0269(11) Uani 1 1 d . . . . .
O1 O 0.0044(8) 0.6966(6) 0.2360(2) 0.0335(15) Uani 1 1 d . U . . .
O2 O 0.1433(6) 0.6777(5) 0.34574(19) 0.0233(12) Uani 1 1 d . U . . .
O3 O 0.0582(6) 0.5513(5) 0.44560(18) 0.0195(11) Uani 1 1 d . . . . .
O4 O 0.2429(6) 0.2729(5) 0.48765(19) 0.0201(12) Uani 1 1 d . . . . .
H4 H 0.2346 0.2076 0.5094 0.024 Uiso 1 1 d R U . . .
N1 N 0.6721(7) 0.5214(6) 0.3546(2) 0.0174(13) Uani 1 1 d . . . . .
C1 C 0.3406(10) 0.5324(7) 0.2100(3) 0.0243(17) Uani 1 1 d . U . . .
H1 H 0.3845 0.4912 0.1801 0.029 Uiso 1 1 calc R U . . .
C2 C 0.2119(10) 0.5973(8) 0.2035(3) 0.0274(19) Uani 1 1 d . . . . .
H2 H 0.1734 0.6036 0.1683 0.033 Uiso 1 1 calc R U . . .
C3 C 0.1382(10) 0.6529(7) 0.2464(3) 0.0247(18) Uani 1 1 d . . . . .
C4 C 0.2044(9) 0.6481(7) 0.2964(3) 0.0232(16) Uani 1 1 d . U . . .
C5 C 0.2467(8) 0.6390(7) 0.3876(3) 0.0166(15) Uani 1 1 d . . . . .
H5 H 0.2655 0.7154 0.4119 0.020 Uiso 1 1 calc R U . . .
C6 C 0.1907(8) 0.5219(6) 0.4213(2) 0.0161(14) Uani 1 1 d . . . . .
C7 C 0.3074(8) 0.4952(6) 0.4634(2) 0.0139(13) Uani 1 1 d . . . . .
H7 H 0.3286 0.5816 0.4808 0.017 Uiso 1 1 calc R U . . .
C8 C 0.4464(9) 0.4503(7) 0.4344(2) 0.0193(15) Uani 1 1 d . . . . .
H8A H 0.5248 0.5079 0.4454 0.023 Uiso 1 1 calc R U . . .
H8B H 0.4696 0.3591 0.4449 0.023 Uiso 1 1 calc R U . . .
C9 C 0.5572(8) 0.4324(7) 0.3382(3) 0.0170(14) Uani 1 1 d . . . . .
H9 H 0.5885 0.3406 0.3460 0.020 Uiso 1 1 calc R U . . .
C10 C 0.5229(9) 0.4397(7) 0.2759(3) 0.0200(15) Uani 1 1 d . U . . .
H10A H 0.6078 0.4697 0.2567 0.024 Uiso 1 1 calc R U . . .
H10B H 0.5010 0.3501 0.2630 0.024 Uiso 1 1 calc R U . . .
C11 C 0.4035(9) 0.5290(7) 0.2610(3) 0.0209(17) Uani 1 1 d . . . . .
C12 C 0.3367(9) 0.5979(7) 0.3011(3) 0.0211(16) Uani 1 1 d . U . . .
C13 C 0.3819(8) 0.5993(6) 0.3590(3) 0.0155(14) Uani 1 1 d . U . . .
C14 C 0.4248(9) 0.4586(7) 0.3730(3) 0.0168(15) Uani 1 1 d . . . . .
C15 C 0.4980(10) 0.6959(7) 0.3704(3) 0.0255(18) Uani 1 1 d . . . . .
H15A H 0.5120 0.7017 0.4098 0.031 Uiso 1 1 calc R U . . .
H15B H 0.4689 0.7838 0.3575 0.031 Uiso 1 1 calc R U . . .
C16 C 0.6375(9) 0.6597(7) 0.3437(3) 0.0207(16) Uani 1 1 d . . . . .
H16A H 0.6310 0.6739 0.3043 0.025 Uiso 1 1 calc R U . . .
H16B H 0.7126 0.7170 0.3579 0.025 Uiso 1 1 calc R U . . .
C17 C 0.8051(9) 0.4905(8) 0.3290(3) 0.0244(17) Uani 1 1 d . . . . .
H17A H 0.7998 0.5119 0.2905 0.037 Uiso 1 1 calc R U . . .
H17C H 0.8251 0.3967 0.3333 0.037 Uiso 1 1 calc R U . . .
H17B H 0.8797 0.5421 0.3458 0.037 Uiso 1 1 calc R U . . .
C18 C 0.1706(8) 0.4046(6) 0.3842(2) 0.0142(14) Uani 1 1 d . . . . .
H18A H 0.1057 0.4286 0.3546 0.017 Uiso 1 1 calc R U . . .
H18B H 0.1282 0.3313 0.4047 0.017 Uiso 1 1 calc R U . . .
C19 C 0.3110(8) 0.3601(6) 0.3602(3) 0.0149(13) Uani 1 1 d . U . . .
H19A H 0.3366 0.2733 0.3752 0.018 Uiso 1 1 calc R U . . .
H19B H 0.3018 0.3510 0.3206 0.018 Uiso 1 1 calc R U . . .
C20 C 0.2775(9) 0.3965(7) 0.5103(2) 0.0174(15) Uani 1 1 d . . . . .
C21 C 0.4019(9) 0.3858(8) 0.5483(3) 0.0220(16) Uani 1 1 d . . . . .
H21A H 0.3805 0.3228 0.5770 0.033 Uiso 1 1 calc R U . . .
H21B H 0.4213 0.4720 0.5642 0.033 Uiso 1 1 calc R U . . .
H21C H 0.4841 0.3558 0.5281 0.033 Uiso 1 1 calc R U . . .
C22 C 0.1495(9) 0.4361(7) 0.5439(3) 0.0205(15) Uani 1 1 d . U . . .
H22 H 0.0635 0.4376 0.5209 0.025 Uiso 1 1 calc R U . . .
C23 C -0.0448(12) 0.8085(8) 0.2666(3) 0.035(2) Uani 1 1 d . U . . .
H23A H -0.1322 0.8411 0.2509 0.052 Uiso 1 1 calc R U . . .
H23B H 0.0259 0.8782 0.2657 0.052 Uiso 1 1 calc R U . . .
H23C H -0.0614 0.7821 0.3041 0.052 Uiso 1 1 calc R U . . .
C24 C 0.0376(11) 0.6831(8) 0.4654(3) 0.033(2) Uani 1 1 d . U . . .
H24A H 0.1235 0.7137 0.4829 0.049 Uiso 1 1 calc R U . . .
H24B H -0.0394 0.6838 0.4914 0.049 Uiso 1 1 calc R U . . .
H24C H 0.0149 0.7413 0.4351 0.049 Uiso 1 1 calc R U . . .
O2S O 0.2918(6) 0.0486(5) 0.54627(18) 0.0208(11) Uani 1 1 d . . . . .
H2SD H 0.2695 0.0183 0.5736 0.025 Uiso 1 1 d R U . . .
H2SE H 0.3762 0.0440 0.5408 0.025 Uiso 1 1 d R U . . .
O1S O 0.2334(16) 0.9278(18) 0.4460(6) 0.028(3) Uani 0.515(11) 1 d D U P A 1
H1S H 0.2975 0.9432 0.4737 0.034 Uiso 0.515(11) 1 d DR U P A 1
C1S C 0.2825(19) 1.0205(14) 0.4074(5) 0.025(3) Uani 0.515(11) 1 d D U P A 1
H1SA H 0.3842 1.0088 0.4017 0.030 Uiso 0.515(11) 1 calc R U P A 1
H1SB H 0.2662 1.1108 0.4207 0.030 Uiso 0.515(11) 1 calc R U P A 1
C2S C 0.2064(18) 1.0005(15) 0.3552(5) 0.024(2) Uani 0.515(11) 1 d D U P A 1
H2SA H 0.2286 1.0727 0.3304 0.036 Uiso 0.515(11) 1 calc R U P A 1
H2SB H 0.1054 0.9988 0.3619 0.036 Uiso 0.515(11) 1 calc R U P A 1
H2SC H 0.2354 0.9171 0.3390 0.036 Uiso 0.515(11) 1 calc R U P A 1
O1'S O 0.2886(16) 0.944(2) 0.4390(7) 0.028(3) Uani 0.485(11) 1 d D . P A 2
H1'S H 0.2434 0.9593 0.4708 0.034 Uiso 0.485(11) 1 d DR U P A 2
C1'S C 0.211(2) 1.0119(16) 0.3978(6) 0.025(3) Uani 0.485(11) 1 d D U P A 2
H1'A H 0.1964 1.1043 0.4090 0.030 Uiso 0.485(11) 1 calc R U P A 2
H1'B H 0.1182 0.9703 0.3936 0.030 Uiso 0.485(11) 1 calc R U P A 2
C2'S C 0.2871(19) 1.0091(16) 0.3444(6) 0.024(2) Uani 0.485(11) 1 d D U P A 2
H2'A H 0.2410 1.0691 0.3191 0.036 Uiso 0.485(11) 1 calc R U P A 2
H2'B H 0.2852 0.9197 0.3298 0.036 Uiso 0.485(11) 1 calc R U P A 2
H2'C H 0.3844 1.0367 0.3497 0.036 Uiso 0.485(11) 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 0.0033 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 C23 117.2(7) . . ?
C4 O2 C5 106.1(6) . . ?
C6 O3 C24 117.2(6) . . ?
C20 O4 H4 117.4 . . ?
C16 N1 C9 111.6(6) . . ?
C17 N1 C9 113.2(5) . . ?
C17 N1 C16 108.8(6) . . ?
C2 C1 H1 120.3 . . ?
C11 C1 H1 120.3 . . ?
C11 C1 C2 119.5(7) . . ?
C1 C2 H2 118.5 . . ?
C3 C2 C1 122.9(7) . . ?
C3 C2 H2 118.5 . . ?
O1 C3 C2 117.2(7) . . ?
O1 C3 C4 126.8(7) . . ?
C4 C3 C2 115.8(8) . . ?
O2 C4 C3 125.8(8) . . ?
C12 C4 O2 113.2(6) . . ?
C12 C4 C3 120.6(7) . . ?
O2 C5 H5 109.5 . . ?
O2 C5 C6 110.5(6) . . ?
O2 C5 C13 108.0(5) . . ?
C6 C5 H5 109.5 . . ?
C13 C5 H5 109.5 . . ?
C13 C5 C6 109.7(6) . . ?
O3 C6 C5 111.8(5) . . ?
O3 C6 C7 112.8(5) . . ?
O3 C6 C18 107.9(6) . . ?
C5 C6 C7 104.4(6) . . ?
C18 C6 C5 108.8(5) . . ?
C18 C6 C7 111.2(5) . . ?
C6 C7 H7 106.3 . . ?
C6 C7 C8 110.4(5) . . ?
C6 C7 C20 118.8(6) . . ?
C8 C7 H7 106.3 . . ?
C20 C7 H7 106.3 . . ?
C20 C7 C8 107.9(5) . . ?
C7 C8 H8A 109.9 . . ?
C7 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
C14 C8 C7 108.8(6) . . ?
C14 C8 H8A 109.9 . . ?
C14 C8 H8B 109.9 . . ?
N1 C9 H9 107.2 . . ?
N1 C9 C10 113.2(6) . . ?
N1 C9 C14 110.2(5) . . ?
C10 C9 H9 107.2 . . ?
C14 C9 H9 107.2 . . ?
C14 C9 C10 111.4(6) . . ?
C9 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C11 C10 C9 115.3(6) . . ?
C11 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C1 C11 C10 124.3(6) . . ?
C12 C11 C1 116.2(7) . . ?
C12 C11 C10 118.8(6) . . ?
C4 C12 C11 123.9(7) . . ?
C4 C12 C13 110.2(6) . . ?
C11 C12 C13 124.3(7) . . ?
C5 C13 C14 111.7(6) . . ?
C12 C13 C5 101.7(6) . . ?
C12 C13 C14 106.6(5) . . ?
C12 C13 C15 113.4(6) . . ?
C15 C13 C5 111.2(6) . . ?
C15 C13 C14 111.8(6) . . ?
C8 C14 C9 115.5(6) . . ?
C13 C14 C8 108.1(5) . . ?
C13 C14 C9 104.6(6) . . ?
C19 C14 C8 105.6(6) . . ?
C19 C14 C9 110.8(5) . . ?
C19 C14 C13 112.4(6) . . ?
C13 C15 H15A 108.8 . . ?
C13 C15 H15B 108.8 . . ?
C13 C15 C16 113.7(6) . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
N1 C16 C15 110.3(6) . . ?
N1 C16 H16A 109.6 . . ?
N1 C16 H16B 109.6 . . ?
C15 C16 H16A 109.6 . . ?
C15 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17C 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17C C17 H17B 109.5 . . ?
C6 C18 H18A 109.5 . . ?
C6 C18 H18B 109.5 . . ?
C6 C18 C19 110.8(6) . . ?
H18A C18 H18B 108.1 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
C14 C19 C18 110.6(5) . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 108.1 . . ?
O4 C20 C7 108.5(5) . . ?
O4 C20 C21 111.4(6) . . ?
O4 C20 C22 105.2(6) . . ?
C21 C20 C7 111.3(6) . . ?
C21 C20 C22 107.9(5) . . ?
C22 C20 C7 112.4(6) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
F1 C22 F2 105.2(5) . . ?
F1 C22 C20 110.8(6) . . ?
F1 C22 H22 110.5 . . ?
F2 C22 C20 109.1(6) . . ?
F2 C22 H22 110.5 . . ?
C20 C22 H22 110.5 . . ?
O1 C23 H23A 109.5 . . ?
O1 C23 H23B 109.5 . . ?
O1 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O3 C24 H24A 109.5 . . ?
O3 C24 H24B 109.5 . . ?
O3 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
H2SD O2S H2SE 113.2 . . ?
C1S O1S H1S 99.7 . . ?
O1S C1S H1SA 109.8 . . ?
O1S C1S H1SB 109.8 . . ?
O1S C1S C2S 109.4(14) . . ?
H1SA C1S H1SB 108.3 . . ?
C2S C1S H1SA 109.8 . . ?
C2S C1S H1SB 109.8 . . ?
C1S C2S H2SA 109.5 . . ?
C1S C2S H2SB 109.5 . . ?
C1S C2S H2SC 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?
C1'S O1'S H1'S 106.8 . . ?
O1'S C1'S H1'A 109.3 . . ?
O1'S C1'S H1'B 109.3 . . ?
O1'S C1'S C2'S 111.5(15) . . ?
H1'A C1'S H1'B 108.0 . . ?
C2'S C1'S H1'A 109.3 . . ?
C2'S C1'S H1'B 109.3 . . ?
C1'S C2'S H2'A 109.5 . . ?
C1'S C2'S H2'B 109.5 . . ?
C1'S C2'S H2'C 109.5 . . ?
H2'A C2'S H2'B 109.5 . . ?
H2'A C2'S H2'C 109.5 . . ?
H2'B C2'S H2'C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C22 1.366(8) . ?
F2 C22 1.379(8) . ?
O1 C3 1.378(11) . ?
O1 C23 1.449(10) . ?
O2 C4 1.389(9) . ?
O2 C5 1.486(8) . ?
O3 C6 1.435(9) . ?
O3 C24 1.442(9) . ?
O4 H4 0.8604 . ?
O4 C20 1.418(8) . ?
N1 C9 1.481(9) . ?
N1 C16 1.472(9) . ?
N1 C17 1.456(10) . ?
C1 H1 0.9500 . ?
C1 C2 1.406(12) . ?
C1 C11 1.400(10) . ?
C2 H2 0.9500 . ?
C2 C3 1.397(11) . ?
C3 C4 1.394(10) . ?
C4 C12 1.369(12) . ?
C5 H5 1.0000 . ?
C5 C6 1.552(9) . ?
C5 C13 1.528(10) . ?
C6 C7 1.553(10) . ?
C6 C18 1.520(9) . ?
C7 H7 1.0000 . ?
C7 C8 1.578(10) . ?
C7 C20 1.564(9) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C14 1.540(9) . ?
C9 H9 1.0000 . ?
C9 C10 1.580(9) . ?
C9 C14 1.556(10) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.505(11) . ?
C11 C12 1.376(10) . ?
C12 C13 1.499(9) . ?
C13 C14 1.530(9) . ?
C13 C15 1.509(11) . ?
C14 C19 1.513(10) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.533(12) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17C 0.9800 . ?
C17 H17B 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.536(10) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.520(11) . ?
C20 C22 1.534(10) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22 1.0000 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
O2S H2SD 0.7755 . ?
O2S H2SE 0.8192 . ?
O1S H1S 0.9341 . ?
O1S C1S 1.424(16) . ?
C1S H1SA 0.9900 . ?
C1S H1SB 0.9900 . ?
C1S C2S 1.499(18) . ?
C2S H2SA 0.9800 . ?
C2S H2SB 0.9800 . ?
C2S H2SC 0.9800 . ?
O1'S H1'S 0.9130 . ?
O1'S C1'S 1.439(18) . ?
C1'S H1'A 0.9900 . ?
C1'S H1'B 0.9900 . ?
C1'S C2'S 1.511(17) . ?
C2'S H2'A 0.9800 . ?
C2'S H2'B 0.9800 . ?
C2'S H2'C 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
O1 C3 C4 O2 5.1(13) . . . . ?
O1 C3 C4 C12 177.7(8) . . . . ?
O2 C4 C12 C11 161.6(7) . . . . ?
O2 C4 C12 C13 -4.5(9) . . . . ?
O2 C5 C6 O3 -56.6(7) . . . . ?
O2 C5 C6 C7 -178.9(5) . . . . ?
O2 C5 C6 C18 62.4(7) . . . . ?
O2 C5 C13 C12 -8.8(7) . . . . ?
O2 C5 C13 C14 -122.1(6) . . . . ?
O2 C5 C13 C15 112.2(6) . . . . ?
O3 C6 C7 C8 174.6(5) . . . . ?
O3 C6 C7 C20 49.3(8) . . . . ?
O3 C6 C18 C19 -175.3(5) . . . . ?
O4 C20 C22 F1 -179.5(5) . . . . ?
O4 C20 C22 F2 65.2(7) . . . . ?
N1 C9 C10 C11 -96.4(8) . . . . ?
N1 C9 C14 C8 -54.9(8) . . . . ?
N1 C9 C14 C13 63.9(7) . . . . ?
N1 C9 C14 C19 -174.8(5) . . . . ?
C1 C2 C3 O1 -170.7(7) . . . . ?
C1 C2 C3 C4 4.1(12) . . . . ?
C1 C11 C12 C4 11.7(11) . . . . ?
C1 C11 C12 C13 175.8(7) . . . . ?
C2 C1 C11 C10 166.2(7) . . . . ?
C2 C1 C11 C12 -3.8(11) . . . . ?
C2 C3 C4 O2 -169.1(7) . . . . ?
C2 C3 C4 C12 3.5(11) . . . . ?
C3 C4 C12 C11 -11.9(12) . . . . ?
C3 C4 C12 C13 -177.9(7) . . . . ?
C4 O2 C5 C6 -113.3(6) . . . . ?
C4 O2 C5 C13 6.7(7) . . . . ?
C4 C12 C13 C5 8.1(8) . . . . ?
C4 C12 C13 C14 125.2(7) . . . . ?
C4 C12 C13 C15 -111.4(7) . . . . ?
C5 O2 C4 C3 171.5(7) . . . . ?
C5 O2 C4 C12 -1.5(8) . . . . ?
C5 C6 C7 C8 -63.8(6) . . . . ?
C5 C6 C7 C20 170.8(5) . . . . ?
C5 C6 C18 C19 63.3(7) . . . . ?
C5 C13 C14 C8 -59.7(8) . . . . ?
C5 C13 C14 C9 176.7(6) . . . . ?
C5 C13 C14 C19 56.4(7) . . . . ?
C5 C13 C15 C16 178.8(6) . . . . ?
C6 C5 C13 C12 111.7(6) . . . . ?
C6 C5 C13 C14 -1.6(8) . . . . ?
C6 C5 C13 C15 -127.3(6) . . . . ?
C6 C7 C8 C14 4.7(8) . . . . ?
C6 C7 C20 O4 58.6(8) . . . . ?
C6 C7 C20 C21 -178.4(6) . . . . ?
C6 C7 C20 C22 -57.3(8) . . . . ?
C6 C18 C19 C14 -9.2(7) . . . . ?
C7 C6 C18 C19 -51.1(7) . . . . ?
C7 C8 C14 C9 173.5(6) . . . . ?
C7 C8 C14 C13 56.7(8) . . . . ?
C7 C8 C14 C19 -63.7(7) . . . . ?
C7 C20 C22 F1 -61.6(8) . . . . ?
C7 C20 C22 F2 -176.9(6) . . . . ?
C8 C7 C20 O4 -67.9(8) . . . . ?
C8 C7 C20 C21 55.0(7) . . . . ?
C8 C7 C20 C22 176.1(6) . . . . ?
C8 C14 C19 C18 67.6(7) . . . . ?
C9 N1 C16 C15 54.5(7) . . . . ?
C9 C10 C11 C1 -168.3(7) . . . . ?
C9 C10 C11 C12 1.3(10) . . . . ?
C9 C14 C19 C18 -166.7(5) . . . . ?
C10 C9 C14 C8 178.6(6) . . . . ?
C10 C9 C14 C13 -62.6(7) . . . . ?
C10 C9 C14 C19 58.7(7) . . . . ?
C10 C11 C12 C4 -158.8(7) . . . . ?
C10 C11 C12 C13 5.3(12) . . . . ?
C11 C1 C2 C3 -3.9(12) . . . . ?
C11 C12 C13 C5 -157.9(7) . . . . ?
C11 C12 C13 C14 -40.8(10) . . . . ?
C11 C12 C13 C15 82.6(9) . . . . ?
C12 C13 C14 C8 -169.9(7) . . . . ?
C12 C13 C14 C9 66.5(7) . . . . ?
C12 C13 C14 C19 -53.8(7) . . . . ?
C12 C13 C15 C16 -67.4(8) . . . . ?
C13 C5 C6 O3 -175.6(5) . . . . ?
C13 C5 C6 C7 62.1(6) . . . . ?
C13 C5 C6 C18 -56.6(8) . . . . ?
C13 C14 C19 C18 -50.1(7) . . . . ?
C13 C15 C16 N1 -49.0(8) . . . . ?
C14 C9 C10 C11 28.5(9) . . . . ?
C14 C13 C15 C16 53.1(7) . . . . ?
C15 C13 C14 C8 65.7(8) . . . . ?
C15 C13 C14 C9 -57.9(7) . . . . ?
C15 C13 C14 C19 -178.2(5) . . . . ?
C16 N1 C9 C10 60.8(7) . . . . ?
C16 N1 C9 C14 -64.8(7) . . . . ?
C17 N1 C9 C10 -62.4(8) . . . . ?
C17 N1 C9 C14 172.1(5) . . . . ?
C17 N1 C16 C15 -179.8(6) . . . . ?
C18 C6 C7 C8 53.3(7) . . . . ?
C18 C6 C7 C20 -72.1(7) . . . . ?
C20 C7 C8 C14 136.0(6) . . . . ?
C21 C20 C22 F1 61.5(7) . . . . ?
C21 C20 C22 F2 -53.8(8) . . . . ?
C23 O1 C3 C2 -148.4(7) . . . . ?
C23 O1 C3 C4 37.4(11) . . . . ?
C24 O3 C6 C5 -37.5(8) . . . . ?
C24 O3 C6 C7 79.8(7) . . . . ?
C24 O3 C6 C18 -157.0(6) . . . . ?
