#------------------------------------------------------------------------------
#$Date: 2025-05-24 05:01:59 +0300 (Sat, 24 May 2025) $
#$Revision: 299808 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/35/2023516.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2023516
loop_
_publ_author_name
'Burkin, Gleb M.'
'Annadurdyyeva, Selbi'
'Kutasevich, Alexandra G.'
'Guliyeva, Narmina A.'
'Hasanov, Khudayar I.'
'Akkurt, Mehmet'
'Manahelohe, Gizachew Mulugeta'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of dimethyl
 3-methyl-8-{[4-(trifluoromethyl)phenyl]sulfonyl}-7,8-dihydro-4H-4,6a-epoxybenzo[b]naphtho[1,8-de]azepine-5,6-dicarboxylate
;
_journal_coeditor_code           NX2026
_journal_issue                   6
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989025004426
_journal_volume                  81
_journal_year                    2025
_chemical_formula_iupac          'C29 H22 F3 N O7 S'
_chemical_formula_moiety         'C29 H22 F3 N O7 S'
_chemical_formula_sum            'C29 H22 F3 N O7 S'
_chemical_formula_weight         585.53
_chemical_name_systematic
;Dimethyl
3-methyl-8-{[4-(trifluoromethyl)phenyl]sulfonyl}-7,8-dihydro-4H-4,6a-epoxybenzo[b]naphtho[1,8-de]azepine-5,6-dicarboxylate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                90
_cell_angle_beta                 93.9830(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6375(5)
_cell_length_b                   11.0324(6)
_cell_length_c                   30.2019(8)
_cell_measurement_reflns_used    20964
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.92
_cell_measurement_theta_min      2.93
_cell_volume                     2538.7(2)
_computing_cell_refinement
;
CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)
;
_computing_data_collection
;
CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)
;
_computing_data_reduction
;
CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2016/6 (Sheldrick, 2015b
;
_computing_structure_solution
;
SHELXT2016/6 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
'Rigaku XtaLAB Synergy-S, HyPix-6000HE area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            31570
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.131
_diffrn_reflns_theta_min         2.933
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.794
_exptl_absorpt_correction_T_max  0.737
_exptl_absorpt_correction_T_min  0.713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2021)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_description       prism
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.430
_refine_ls_extinction_coef       0.00089(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL-2019/2 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5526
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0633P)²+0.8141P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1028
_reflns_number_gt                5187
_reflns_number_total             5526
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            nx2026.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2023516
_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_min   0.572
_shelx_estimated_absorpt_t_max   0.750
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 -0.08268(3) 0.68046(3) 0.60331(2) 0.01536(10) Uani d 1 . .
F F1 0.03672(12) 0.08285(8) 0.60261(3) 0.0324(2) Uani d 1 . .
F F2 0.22478(16) 0.13678(9) 0.55695(5) 0.0501(3) Uani d 1 . .
F F3 0.29014(14) 0.14333(10) 0.62756(5) 0.0539(3) Uani d 1 . .
O O1 -0.16062(12) 0.70213(9) 0.64434(3) 0.0216(2) Uani d 1 . .
O O2 -0.17402(12) 0.70996(9) 0.56162(3) 0.0225(2) Uani d 1 . .
C C1 0.48862(15) 0.49339(11) 0.57852(4) 0.0171(2) Uani d 1 . .
H H1 0.496038 0.479440 0.547665 0.021 Uiso calc 1 . .
C C2 0.55556(16) 0.40746(11) 0.60859(4) 0.0187(2) Uani d 1 . .
H H2 0.607100 0.336071 0.597644 0.022 Uiso calc 1 . .
C C3 0.54990(15) 0.42217(11) 0.65483(4) 0.0172(2) Uani d 1 . .
C C3A 0.47063(15) 0.52723(11) 0.66816(4) 0.0156(2) Uani d 1 . .
C C4 0.44151(15) 0.58212(12) 0.71373(4) 0.0171(2) Uani d 1 . .
H H4 0.444763 0.524274 0.739264 0.021 Uiso calc 1 . .
C C5 0.56803(16) 0.69088(11) 0.71852(4) 0.0165(2) Uani d 1 . .
C C6 0.50225(15) 0.77414(11) 0.68956(4) 0.0149(2) Uani d 1 . .
C C6A 0.33411(15) 0.71572(11) 0.66698(4) 0.0141(2) Uani d 1 . .
C C7 0.18668(15) 0.79745(11) 0.64834(4) 0.0158(2) Uani d 1 . .
H H7A 0.096592 0.803245 0.670287 0.019 Uiso calc 1 . .
H H7B 0.234316 0.879823 0.644221 0.019 Uiso calc 1 . .
N N8 0.10246(13) 0.75554(9) 0.60592(3) 0.0148(2) Uani d 1 . .
C C8A 0.19749(15) 0.76703(11) 0.56657(4) 0.0144(2) Uani d 1 . .
C C9 0.14221(16) 0.85518(12) 0.53567(4) 0.0186(2) Uani d 1 . .
H H9 0.041411 0.902688 0.540357 0.022 Uiso calc 1 . .
C C10 0.23335(17) 0.87407(12) 0.49810(4) 0.0217(3) Uani d 1 . .
H H10 0.195141 0.934034 0.477015 0.026 Uiso calc 1 . .
C C11 0.38118(17) 0.80441(12) 0.49158(4) 0.0202(3) Uani d 1 . .
H H11 0.445235 0.817581 0.466155 0.024 Uiso calc 1 . .
C C12 0.43538(16) 0.71573(12) 0.52212(4) 0.0171(2) Uani d 1 . .
H H12 0.535760 0.668175 0.517074 0.020 Uiso calc 1 . .
C C12A 0.34499(15) 0.69485(11) 0.56029(4) 0.0143(2) Uani d 1 . .
C C12B 0.40963(14) 0.60123(11) 0.59260(4) 0.0144(2) Uani d 1 . .
C C12C 0.40171(14) 0.61400(11) 0.63793(4) 0.0137(2) Uani d 1 . .
O O13 0.27786(11) 0.64524(8) 0.70381(3) 0.01706(19) Uani d 1 . .
C C13 0.6235(19) 0.3275(12) 0.6870(4) 0.0238(3) Uani d 0.53(2) A 1
H H13A 0.732679 0.294903 0.676576 0.036 Uiso calc 0.53(2) A 1
H H13B 0.538176 0.261703 0.689067 0.036 Uiso calc 0.53(2) A 1
H H13C 0.647483 0.364271 0.716356 0.036 Uiso calc 0.53(2) A 1
C C13' 0.625(2) 0.3275(13) 0.6867(5) 0.0238(3) Uani d 0.47(2) A 2
H H13D 0.747394 0.348027 0.695799 0.036 Uiso calc 0.47(2) A 2
H H13E 0.621140 0.248114 0.672104 0.036 Uiso calc 0.47(2) A 2
H H13F 0.556513 0.324858 0.712874 0.036 Uiso calc 0.47(2) A 2
C C14 0.74252(17) 0.68539(12) 0.74318(4) 0.0187(3) Uani d 1 . .
O O14 0.82551(14) 0.77048(10) 0.75805(4) 0.0298(2) Uani d 1 . .
O O15 0.79316(12) 0.56938(9) 0.74709(3) 0.0221(2) Uani d 1 . .
C C15 0.96586(17) 0.54877(14) 0.76935(5) 0.0252(3) Uani d 1 . .
H H15A 1.051895 0.601521 0.756353 0.038 Uiso calc 1 . .
H H15B 0.999568 0.463854 0.765660 0.038 Uiso calc 1 . .
H H15C 0.962354 0.567077 0.801032 0.038 Uiso calc 1 . .
C C16 0.58807(15) 0.88141(11) 0.67119(4) 0.0160(2) Uani d 1 . .
O O16 0.68066(13) 0.95432(9) 0.69113(3) 0.0247(2) Uani d 1 . .
O O17 0.54422(11) 0.88538(8) 0.62730(3) 0.01773(19) Uani d 1 . .
C C17 0.63324(19) 0.97498(13) 0.60257(5) 0.0244(3) Uani d 1 . .
H H17A 0.585829 0.974193 0.571579 0.037 Uiso calc 1 . .
H H17B 0.759006 0.956514 0.603902 0.037 Uiso calc 1 . .
H H17C 0.615553 1.055289 0.615390 0.037 Uiso calc 1 . .
C C18 -0.02522(15) 0.52580(11) 0.60113(4) 0.0161(2) Uani d 1 . .
C C19 -0.01841(17) 0.47033(12) 0.56005(4) 0.0213(3) Uani d 1 . .
H H19 -0.055255 0.512804 0.533666 0.026 Uiso calc 1 . .
C C20 0.04285(18) 0.35202(13) 0.55788(5) 0.0241(3) Uani d 1 . .
H H20 0.049166 0.312688 0.530058 0.029 Uiso calc 1 . .
C C21 0.09484(17) 0.29210(12) 0.59721(5) 0.0220(3) Uani d 1 . .
C C22 0.08252(17) 0.34703(12) 0.63835(5) 0.0224(3) Uani d 1 . .
H H22 0.115329 0.303757 0.664827 0.027 Uiso calc 1 . .
C C23 0.02216(17) 0.46516(12) 0.64049(4) 0.0195(3) Uani d 1 . .
H H23 0.013327 0.503979 0.668321 0.023 Uiso calc 1 . .
C C24 0.16202(19) 0.16488(13) 0.59579(6) 0.0296(3) Uani d 1 . .
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'
S S 0.3331 0.5567 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 S1 O2 . . 121.06(6) ?
O1 S1 N8 . . 106.49(6) ?
O2 S1 N8 . . 107.06(5) ?
O1 S1 C18 . . 108.27(6) ?
O2 S1 C18 . . 107.08(6) ?
N8 S1 C18 . . 105.97(5) ?
C2 C1 C12B . . 121.64(11) ?
C2 C1 H1 . . 119.2 ?
C12B C1 H1 . . 119.2 ?
C1 C2 C3 . . 122.36(11) ?
C1 C2 H2 . . 118.8 ?
C3 C2 H2 . . 118.8 ?
C3A C3 C2 . . 115.46(11) ?
C3A C3 C13' . . 123.5(7) ?
C2 C3 C13' . . 121.1(7) ?
C3A C3 C13 . . 123.0(6) ?
C2 C3 C13 . . 121.5(6) ?
C3 C3A C12C . . 122.45(11) ?
C3 C3A C4 . . 133.39(11) ?
C12C C3A C4 . . 104.11(10) ?
O13 C4 C3A . . 100.46(9) ?
O13 C4 C5 . . 99.91(10) ?
C3A C4 C5 . . 105.22(9) ?
O13 C4 H4 . . 116.3 ?
C3A C4 H4 . . 116.3 ?
C5 C4 H4 . . 116.3 ?
C6 C5 C14 . . 129.68(12) ?
C6 C5 C4 . . 105.54(11) ?
C14 C5 C4 . . 123.47(11) ?
C5 C6 C16 . . 129.54(11) ?
C5 C6 C6A . . 105.26(10) ?
C16 C6 C6A . . 122.82(10) ?
O13 C6A C7 . . 110.59(9) ?
O13 C6A C12C . . 100.14(9) ?
C7 C6A C12C . . 119.46(10) ?
O13 C6A C6 . . 99.57(9) ?
C7 C6A C6 . . 119.05(10) ?
C12C C6A C6 . . 104.71(9) ?
N8 C7 C6A . . 113.89(10) ?
N8 C7 H7A . . 108.8 ?
C6A C7 H7A . . 108.8 ?
N8 C7 H7B . . 108.8 ?
C6A C7 H7B . . 108.8 ?
H7A C7 H7B . . 107.7 ?
C8A N8 C7 . . 118.49(9) ?
C8A N8 S1 . . 119.23(8) ?
C7 N8 S1 . . 121.75(8) ?
C9 C8A C12A . . 120.98(11) ?
C9 C8A N8 . . 117.87(11) ?
C12A C8A N8 . . 121.12(10) ?
C10 C9 C8A . . 120.45(12) ?
C10 C9 H9 . . 119.8 ?
C8A C9 H9 . . 119.8 ?
C9 C10 C11 . . 119.40(12) ?
C9 C10 H10 . . 120.3 ?
C11 C10 H10 . . 120.3 ?
C12 C11 C10 . . 120.20(12) ?
C12 C11 H11 . . 119.9 ?
C10 C11 H11 . . 119.9 ?
C11 C12 C12A . . 121.37(11) ?
C11 C12 H12 . . 119.3 ?
C12A C12 H12 . . 119.3 ?
C8A C12A C12 . . 117.59(11) ?
C8A C12A C12B . . 122.72(10) ?
C12 C12A C12B . . 119.67(11) ?
C12C C12B C1 . . 115.67(11) ?
C12C C12B C12A . . 123.09(11) ?
C1 C12B C12A . . 121.22(11) ?
C12B C12C C3A . . 122.41(11) ?
C12B C12C C6A . . 132.85(11) ?
C3A C12C C6A . . 104.66(10) ?
C4 O13 C6A . . 96.88(8) ?
C3 C13 H13A . . 109.5 ?
C3 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C3 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C3 C13' H13D . . 109.5 ?
C3 C13' H13E . . 109.5 ?
H13D C13' H13E . . 109.5 ?
C3 C13' H13F . . 109.5 ?
H13D C13' H13F . . 109.5 ?
H13E C13' H13F . . 109.5 ?
O14 C14 O15 . . 124.85(12) ?
O14 C14 C5 . . 126.04(12) ?
O15 C14 C5 . . 109.10(11) ?
C14 O15 C15 . . 115.88(11) ?
O15 C15 H15A . . 109.5 ?
O15 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O15 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
O16 C16 O17 . . 124.64(12) ?
O16 C16 C6 . . 127.35(12) ?
O17 C16 C6 . . 108.01(10) ?
C16 O17 C17 . . 116.09(10) ?
O17 C17 H17A . . 109.5 ?
O17 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
O17 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C19 C18 C23 . . 121.92(12) ?
C19 C18 S1 . . 119.01(10) ?
C23 C18 S1 . . 118.95(10) ?
C18 C19 C20 . . 119.34(12) ?
C18 C19 H19 . . 120.3 ?
C20 C19 H19 . . 120.3 ?
C19 C20 C21 . . 118.86(12) ?
C19 C20 H20 . . 120.6 ?
C21 C20 H20 . . 120.6 ?
C22 C21 C20 . . 121.45(13) ?
C22 C21 C24 . . 118.61(13) ?
C20 C21 C24 . . 119.93(13) ?
C23 C22 C21 . . 119.65(12) ?
C23 C22 H22 . . 120.2 ?
C21 C22 H22 . . 120.2 ?
C22 C23 C18 . . 118.72(12) ?
C22 C23 H23 . . 120.6 ?
C18 C23 H23 . . 120.6 ?
F2 C24 F3 . . 107.37(13) ?
F2 C24 F1 . . 106.36(13) ?
F3 C24 F1 . . 105.22(13) ?
F2 C24 C21 . . 112.84(13) ?
F3 C24 C21 . . 112.32(13) ?
F1 C24 C21 . . 112.23(11) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O1 . 1.4314(9) ?
S1 O2 . 1.4338(10) ?
S1 N8 . 1.6359(10) ?
S1 C18 . 1.7642(13) ?
F1 C24 . 1.3434(17) ?
F2 C24 . 1.334(2) ?
F3 C24 . 1.343(2) ?
C1 C2 . 1.3857(18) ?
C1 C12B . 1.4129(17) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.4096(18) ?
C2 H2 . 0.9500 ?
C3 C3A . 1.3805(17) ?
C3 C13' . 1.507(10) ?
C3 C13 . 1.509(9) ?
C3A C12C . 1.4001(17) ?
C3A C4 . 1.5340(17) ?
C4 O13 . 1.4439(15) ?
C4 C5 . 1.5411(17) ?
C4 H4 . 1.0000 ?
C5 C6 . 1.3416(18) ?
C5 C14 . 1.4820(17) ?
C6 C16 . 1.4795(17) ?
C6 C6A . 1.5517(16) ?
C6A O13 . 1.4466(13) ?
C6A C7 . 1.5198(16) ?
C6A C12C . 1.5358(16) ?
C7 N8 . 1.4680(15) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
N8 C8A . 1.4405(15) ?
C8A C9 . 1.3928(17) ?
C8A C12A . 1.4031(17) ?
C9 C10 . 1.3877(18) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.3910(19) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.3877(18) ?
C11 H11 . 0.9500 ?
C12 C12A . 1.4034(16) ?
C12 H12 . 0.9500 ?
C12A C12B . 1.4819(17) ?
C12B C12C . 1.3816(16) ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 0.9800 ?
C13' H13D . 0.9800 ?
C13' H13E . 0.9800 ?
C13' H13F . 0.9800 ?
C14 O14 . 1.2022(18) ?
C14 O15 . 1.3400(17) ?
O15 C15 . 1.4562(15) ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
C16 O16 . 1.2045(16) ?
C16 O17 . 1.3452(15) ?
O17 C17 . 1.4378(15) ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
C18 C19 . 1.3876(17) ?
C18 C23 . 1.3899(18) ?
C19 C20 . 1.390(2) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.393(2) ?
C20 H20 . 0.9500 ?
C21 C22 . 1.391(2) ?
C21 C24 . 1.4961(19) ?
C22 C23 . 1.3854(19) ?
C22 H22 . 0.9500 ?
C23 H23 . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C4 H4 O16 2_646 1.00 2.49 3.3893(16) 149 yes
C7 H7A O1 . 0.99 2.35 2.8481(15) 111 yes
C7 H7B O17 . 0.99 2.46 3.0071(14) 115 yes
C12 H12 O2 1_655 0.95 2.55 3.1357(15) 120 yes
C15 H15A O13 1_655 0.98 2.47 3.3741(17) 153 yes
C17 H17B F1 1_665 0.98 2.54 3.3033(17) 135 yes
C19 H19 O2 . 0.95 2.52 2.9003(17) 104 yes
C22 H22 O14 2_646 0.95 2.37 3.2698(19) 158 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C12B C1 C2 C3 . . . . -0.27(19) ?
C1 C2 C3 C3A . . . . 0.97(18) ?
C1 C2 C3 C13' . . . . -179.4(8) ?
C1 C2 C3 C13 . . . . 180.0(7) ?
C2 C3 C3A C12C . . . . -0.53(17) ?
C13' C3 C3A C12C . . . . 179.9(8) ?
C13 C3 C3A C12C . . . . -179.5(7) ?
C2 C3 C3A C4 . . . . -177.38(12) ?
C13' C3 C3A C4 . . . . 3.0(8) ?
C13 C3 C3A C4 . . . . 3.6(7) ?
C3 C3A C4 O13 . . . . -148.68(13) ?
C12C C3A C4 O13 . . . . 34.06(11) ?
C3 C3A C4 C5 . . . . 107.93(15) ?
C12C C3A C4 C5 . . . . -69.34(11) ?
O13 C4 C5 C6 . . . . -33.53(11) ?
C3A C4 C5 C6 . . . . 70.27(12) ?
O13 C4 C5 C14 . . . . 158.45(10) ?
C3A C4 C5 C14 . . . . -97.75(13) ?
C14 C5 C6 C16 . . . . 4.6(2) ?
C4 C5 C6 C16 . . . . -162.42(11) ?
C14 C5 C6 C6A . . . . 167.07(12) ?
C4 C5 C6 C6A . . . . 0.07(12) ?
C5 C6 C6A O13 . . . . 33.30(11) ?
C16 C6 C6A O13 . . . . -162.73(10) ?
C5 C6 C6A C7 . . . . 153.40(10) ?
C16 C6 C6A C7 . . . . -42.62(15) ?
C5 C6 C6A C12C . . . . -69.93(11) ?
C16 C6 C6A C12C . . . . 94.05(12) ?
O13 C6A C7 N8 . . . . -105.16(11) ?
C12C C6A C7 N8 . . . . 10.18(15) ?
C6 C6A C7 N8 . . . . 140.52(10) ?
C6A C7 N8 C8A . . . . -72.75(13) ?
C6A C7 N8 S1 . . . . 98.88(11) ?
O1 S1 N8 C8A . . . . -170.14(9) ?
O2 S1 N8 C8A . . . . -39.32(10) ?
C18 S1 N8 C8A . . . . 74.73(10) ?
O1 S1 N8 C7 . . . . 18.29(11) ?
O2 S1 N8 C7 . . . . 149.11(9) ?
C18 S1 N8 C7 . . . . -96.85(10) ?
C7 N8 C8A C9 . . . . -107.68(13) ?
S1 N8 C8A C9 . . . . 80.47(13) ?
C7 N8 C8A C12A . . . . 70.01(15) ?
S1 N8 C8A C12A . . . . -101.83(12) ?
C12A C8A C9 C10 . . . . -0.56(19) ?
N8 C8A C9 C10 . . . . 177.14(11) ?
C8A C9 C10 C11 . . . . -0.2(2) ?
C9 C10 C11 C12 . . . . 0.9(2) ?
C10 C11 C12 C12A . . . . -0.7(2) ?
C9 C8A C12A C12 . . . . 0.70(17) ?
N8 C8A C12A C12 . . . . -176.93(10) ?
C9 C8A C12A C12B . . . . 179.17(11) ?
N8 C8A C12A C12B . . . . 1.54(17) ?
C11 C12 C12A C8A . . . . -0.05(18) ?
C11 C12 C12A C12B . . . . -178.57(11) ?
C2 C1 C12B C12C . . . . -0.87(17) ?
C2 C1 C12B C12A . . . . 177.47(11) ?
C8A C12A C12B C12C . . . . -34.98(17) ?
C12 C12A C12B C12C . . . . 143.46(12) ?
C8A C12A C12B C1 . . . . 146.80(12) ?
C12 C12A C12B C1 . . . . -34.76(17) ?
C1 C12B C12C C3A . . . . 1.32(17) ?
C12A C12B C12C C3A . . . . -176.99(11) ?
C1 C12B C12C C6A . . . . 177.79(11) ?
C12A C12B C12C C6A . . . . -0.5(2) ?
C3 C3A C12C C12B . . . . -0.65(18) ?
C4 C3A C12C C12B . . . . 177.00(11) ?
C3 C3A C12C C6A . . . . -177.97(11) ?
C4 C3A C12C C6A . . . . -0.32(11) ?
O13 C6A C12C C12B . . . . 149.70(12) ?
C7 C6A C12C C12B . . . . 28.95(18) ?
C6 C6A C12C C12B . . . . -107.51(14) ?
O13 C6A C12C C3A . . . . -33.39(11) ?
C7 C6A C12C C3A . . . . -154.14(10) ?
C6 C6A C12C C3A . . . . 69.41(11) ?
C3A C4 O13 C6A . . . . -54.37(10) ?
C5 C4 O13 C6A . . . . 53.28(10) ?
C7 C6A O13 C4 . . . . -179.14(10) ?
C12C C6A O13 C4 . . . . 53.93(10) ?
C6 C6A O13 C4 . . . . -53.03(10) ?
C6 C5 C14 O14 . . . . 36.1(2) ?
C4 C5 C14 O14 . . . . -158.94(13) ?
C6 C5 C14 O15 . . . . -144.93(13) ?
C4 C5 C14 O15 . . . . 20.01(16) ?
O14 C14 O15 C15 . . . . -3.06(18) ?
C5 C14 O15 C15 . . . . 177.98(10) ?
C5 C6 C16 O16 . . . . -44.8(2) ?
C6A C6 C16 O16 . . . . 155.42(12) ?
C5 C6 C16 O17 . . . . 135.61(13) ?
C6A C6 C16 O17 . . . . -24.19(14) ?
O16 C16 O17 C17 . . . . 8.00(17) ?
C6 C16 O17 C17 . . . . -172.38(10) ?
O1 S1 C18 C19 . . . . 152.89(10) ?
O2 S1 C18 C19 . . . . 20.83(11) ?
N8 S1 C18 C19 . . . . -93.20(11) ?
O1 S1 C18 C23 . . . . -30.97(11) ?
O2 S1 C18 C23 . . . . -163.03(10) ?
N8 S1 C18 C23 . . . . 82.94(11) ?
C23 C18 C19 C20 . . . . -2.14(19) ?
S1 C18 C19 C20 . . . . 173.88(10) ?
C18 C19 C20 C21 . . . . 0.4(2) ?
C19 C20 C21 C22 . . . . 1.6(2) ?
C19 C20 C21 C24 . . . . -179.74(12) ?
C20 C21 C22 C23 . . . . -1.9(2) ?
C24 C21 C22 C23 . . . . 179.43(12) ?
C21 C22 C23 C18 . . . . 0.18(19) ?
C19 C18 C23 C22 . . . . 1.85(19) ?
S1 C18 C23 C22 . . . . -174.17(9) ?
C22 C21 C24 F2 . . . . -158.19(13) ?
C20 C21 C24 F2 . . . . 23.13(19) ?
C22 C21 C24 F3 . . . . -36.65(18) ?
C20 C21 C24 F3 . . . . 144.67(14) ?
C22 C21 C24 F1 . . . . 81.66(17) ?
C20 C21 C24 F1 . . . . -97.02(16) ?
