##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     'SHELXL-2018/3'
_journal_date_recd_electronic     2023-10-27
_journal_date_accepted     2023-11-03
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2023
_journal_volume     79
_journal_issue     12
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989023009635
_journal_coeditor_code     TX2077
_publ_contact_author_name     'Ajaya Bhattarai'
_publ_contact_author_address
;
Department of Chemistry,
M.M.A.M.C (Tribhuvan University)
Biratnagar,
Nepal
;
_publ_contact_author_email     'ajaya.bhattarai@mmamc.tu.edu.np'
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;\
Crystal structure and Hirshfeld surface analysis of
10-hydroxy-2-(4-methoxyphenyl)-3-oxo-2,3,3a,4,10,10a-hexahydro-\
1H-9-thia-2-azacyclopenta[b]fluorene-4-carboxylic acid dimethyl
sulfoxide-d₆ monosolvate
;
loop_
    _publ_author_name
    _publ_author_address
    'Gunay Z. Mammadova'
;
Organic Chemistry Department,
Baku State University,
Z. Xalilov Str. 23, Az 1148 Baku,
Azerbaijan
;
    'Elizaveta D. Yakovleva'
;
Peoples' Friendship University of Russia (RUDN University),
6 Miklukho-Maklaya St., Moscow, 117198,
Russian Federation
;
    'Pavel P. Erokhin'
;
Peoples' Friendship University of Russia (RUDN University),
6 Miklukho-Maklaya St., Moscow, 117198,
Russian Federation
;
    'Mikhail S. Grigoriev'
;
Frumkin Institute of Physical Chemistry and Electrochemistry,
Russian Academy of Sciences,
Leninskiy prospect 31-4, Moscow 119071,
Russian Federation
;
    'Zeliha Atioğlu'
;
Department of Aircraft Electrics and Electronics,
School of Applied Sciences, Cappadocia University,
Mustafapaşa, 50420 Ürgüp,
Nevşehir, Turkey
;
    'Asmet N. Azizova'
;
Department of Synthesis of Biologically Active Compounds,
Scientific Research Center,
Azerbaijan Medical University,
Samed Vurgun St. 167, Az 1022 Baku,
Azerbaijan
;
    'Akkurt, Mehmet'
;
Department of Physics,
Faculty of Sciences,
Erciyes University,
38039 Kayseri,
Turkey
;
    'Ajaya Bhattarai'
;
Department of Chemistry,
M.M.A.M.C (Tribhuvan University)
Biratnagar,
Nepal
;
_publ_section_synopsis
;
In the crystal, molecules are connected by pairs of intermolecular C---H...O
hydrogen bonds, forming dimers with  R²₂(8) motifs. These dimers
form a three-dimensional network through O---H...O, O---H...S and C---H...O
hydrogen bonds with each other directly and through solvent molecules.
;
_chemical_name_systematic
;\
10-Hydroxy-2-(4-methoxyphenyl)-3-oxo-2,3,3a,4,10,10a-hexahydro-\
1H-9-thia-2-azacyclopenta[b]fluorene-4-carboxylic acid dimethyl
sulfoxide-d₆ monosolvate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C22 H19 N O5 S, C2 D6 O S'
_chemical_formula_sum     'C24 H19 D6 N O6 S2'
_chemical_formula_iupac     'C22 H19 N O5 S, C2 D6 O S'
_chemical_formula_weight     493.61
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/c'
_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     16.3178(4)
_cell_length_b     9.2747(2)
_cell_length_c     14.8720(4)
_cell_angle_alpha     90
_cell_angle_beta     93.7710(10)
_cell_angle_gamma     90
_cell_volume     2245.89(10)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9765
_cell_measurement_theta_min     2.59
_cell_measurement_theta_max     30.13
_cell_measurement_temperature     100(2)
_exptl_crystal_description     'fragment'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.400
_exptl_crystal_size_mid     0.280
_exptl_crystal_size_min     0.220
_exptl_crystal_density_diffrn     1.460
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     1024
_exptl_absorpt_coefficient_mu     0.280
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_absorpt_correction_T_min     0.847
_exptl_absorpt_correction_T_max     0.941
_diffrn_ambient_temperature     100(2)
_diffrn_source     ?
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type
                              'Bruker Kappa APEXII area-detector diffractometer'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     69078
_diffrn_reflns_av_R_equivalents     0.0316
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_theta_min     4.211
_diffrn_reflns_theta_max     29.999
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -22
_diffrn_reflns_limit_h_max     22
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     20
_refine_special_details     ?
_reflns_number_total     6531
_reflns_number_gt     5693
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0586
_refine_ls_R_factor_gt     0.0492
_refine_ls_wR_factor_gt     0.1233
_refine_ls_wR_factor_ref     0.1292
_refine_ls_goodness_of_fit_ref     1.123
_refine_ls_restrained_S_all     1.124
_refine_ls_number_reflns     6531
_refine_ls_number_parameters     324
_refine_ls_number_restraints     15
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0518P)²+1.8241P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.537
_refine_diff_density_min     -0.467
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
    'D' 'D' 0.0000 0.0000
                         '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'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
APEX4 (Bruker, 2008)
;
_computing_cell_refinement
;
SAINT (Bruker, 2008)
;
_computing_data_reduction
;
SAINT (Bruker, 2008)
;
_computing_structure_solution
;
SHELXT2016/6 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2016/6 (Sheldrick, 2015b
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
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 S1A 0.06873(3) 0.67027(5) 0.20351(4) 0.03201(16) Uani d 0.8903(18) A 1
    S S1B -0.0094(3) 0.7350(5) 0.2022(3) 0.0386(13) Uiso d 0.1097(18) A 2
    S S5 0.21789(3) 1.16195(5) 0.65744(3) 0.03355(13) Uani d 1 . .
    O O1 0.36715(8) 0.72156(13) 0.33936(8) 0.0253(3) Uani d 1 . .
    O O2 0.14801(9) 0.83115(17) 0.39946(10) 0.0367(3) Uani d 1 . .
    O O3 0.20598(9) 0.93552(15) 0.28380(8) 0.0338(3) Uani d 1 . .
    H H3 0.165707 0.899140 0.253855 0.041 Uiso calc 1 . .
    O O4 0.47133(8) 0.05607(13) 0.38739(8) 0.0275(3) Uani d 1 . .
    O O5A 0.25163(15) 0.8579(2) 0.70428(13) 0.0338(6) Uani d 0.637(4) B 1
    H H5A 0.283755 0.813423 0.741012 0.041 Uiso calc 0.637(4) B 1
    O O5B 0.3604(2) 0.9025(4) 0.6728(2) 0.0282(9) Uani d 0.363(4) B 2
    H H5B 0.358402 0.867406 0.724666 0.034 Uiso calc 0.363(4) B 2
    O O6A 0.08659(10) 0.82728(16) 0.18542(11) 0.0337(4) Uani d 0.8903(18) A 1
    O O6B 0.0447(10) 0.8676(13) 0.2106(10) 0.044(3) Uiso d 0.1097(18) A 2
    N N2 0.35684(8) 0.60178(14) 0.47516(9) 0.0193(3) Uani d 1 . .
    C C1 0.35193(10) 0.71814(17) 0.41916(10) 0.0193(3) Uani d 1 . .
    C C3A 0.29022(10) 0.77925(18) 0.55483(10) 0.0218(3) Uani d 1 . .
    H H3AA 0.232017 0.752657 0.536985 0.026 Uiso calc 1 B 1
    C C3 0.34047(11) 0.64061(18) 0.56878(10) 0.0231(3) Uani d 1 . .
    H H3A 0.392113 0.658285 0.605867 0.028 Uiso calc 1 . .
    H H3B 0.308591 0.564525 0.597492 0.028 Uiso calc 1 . .
    C C4B 0.29054(12) 0.8898(2) 0.63036(11) 0.0302(4) Uani d 0.637(4) B 1
    H H4A 0.349158 0.910797 0.649808 0.036 Uiso calc 0.637(4) B 1
    C C4C 0.29054(12) 0.8898(2) 0.63036(11) 0.0302(4) Uani d 0.363(4) B 2
    H H4B 0.251734 0.853878 0.674610 0.036 Uiso calc 0.363(4) B 2
    C C4A 0.25370(11) 1.02578(19) 0.58966(11) 0.0258(3) Uani d 1 . .
    C C5A 0.19138(11) 1.26951(19) 0.56388(11) 0.0264(3) Uani d 1 . .
    C C6 0.15675(13) 1.4072(2) 0.56345(14) 0.0338(4) Uani d 1 . .
    H H6A 0.143922 1.452519 0.618055 0.041 Uiso calc 1 . .
    C C7 0.14169(12) 1.4755(2) 0.48199(14) 0.0331(4) Uani d 1 . .
    H H7A 0.117404 1.568665 0.480419 0.040 Uiso calc 1 . .
    C C8 0.16150(12) 1.41029(19) 0.40123(13) 0.0295(4) Uani d 1 . .
    H H8A 0.151707 1.460284 0.345810 0.035 Uiso calc 1 . .
    C C9B 0.24595(10) 1.06021(17) 0.50055(10) 0.0204(3) Uani d 1 . .
    C C9A 0.21054(10) 1.20072(17) 0.48381(11) 0.0213(3) Uani d 1 . .
    C C9 0.19531(10) 1.27320(18) 0.40184(11) 0.0238(3) Uani d 1 . .
    H H9A 0.208082 1.228670 0.346961 0.029 Uiso calc 1 . .
    C C10A 0.32805(9) 0.84675(16) 0.47404(10) 0.0187(3) Uani d 1 . .
    H H10A 0.380248 0.894315 0.497193 0.022 Uiso calc 1 . .
    C C10 0.27474(9) 0.96355(16) 0.42751(10) 0.0184(3) Uani d 1 . .
    H H10B 0.309492 1.021507 0.387981 0.022 Uiso calc 1 . .
    C C11 0.20217(10) 0.90191(17) 0.36979(11) 0.0216(3) Uani d 1 . .
    C C12 0.38481(9) 0.46286(16) 0.45148(10) 0.0189(3) Uani d 1 . .
    C C13 0.42078(10) 0.37136(18) 0.51699(11) 0.0218(3) Uani d 1 . .
    H H13A 0.426719 0.402232 0.577975 0.026 Uiso calc 1 . .
    C C14 0.44797(10) 0.23566(18) 0.49391(11) 0.0224(3) Uani d 1 . .
    H H14A 0.471177 0.173102 0.539320 0.027 Uiso calc 1 . .
    C C15 0.44140(10) 0.19057(16) 0.40438(11) 0.0206(3) Uani d 1 . .
    C C16 0.40420(10) 0.28012(17) 0.33900(11) 0.0227(3) Uani d 1 . .
    H H16A 0.398353 0.249190 0.278021 0.027 Uiso calc 1 . .
    C C17 0.37553(10) 0.41479(17) 0.36268(10) 0.0214(3) Uani d 1 . .
    H H17A 0.349271 0.474921 0.317799 0.026 Uiso calc 1 . .
    C C18 0.46796(13) 0.0111(2) 0.29506(13) 0.0319(4) Uani d 1 . .
    H H18A 0.490909 -0.086181 0.291209 0.048 Uiso calc 1 . .
    H H18B 0.410733 0.010725 0.270532 0.048 Uiso calc 1 . .
    H H18C 0.499947 0.078007 0.260286 0.048 Uiso calc 1 . .
    C C19A 0.02185(17) 0.6061(3) 0.0999(2) 0.0471(7) Uani d 0.8903(18) A 1
    D D19A 0.008139 0.503811 0.105923 0.071 Uiso calc 0.8903(18) A 1
    D D19B -0.028387 0.661165 0.084572 0.071 Uiso calc 0.8903(18) A 1
    D D19C 0.059929 0.617892 0.052192 0.071 Uiso calc 0.8903(18) A 1
    C C20A -0.01808(16) 0.6679(3) 0.26878(19) 0.0470(6) Uani d 0.8903(18) A 1
    D D20A -0.032251 0.567942 0.282401 0.070 Uiso calc 0.8903(18) A 1
    D D20B -0.005525 0.720540 0.325154 0.070 Uiso calc 0.8903(18) A 1
    D D20C -0.064553 0.713967 0.234952 0.070 Uiso calc 0.8903(18) A 1
    C C19B 0.0423(13) 0.6018(18) 0.2686(12) 0.049(4) Uiso d 0.1097(18) A 2
    D D19D 0.010074 0.512543 0.265939 0.074 Uiso calc 0.1097(18) A 2
    D D19E 0.096287 0.583660 0.245646 0.074 Uiso calc 0.1097(18) A 2
    D D19F 0.049335 0.635024 0.331200 0.074 Uiso calc 0.1097(18) A 2
    C C20B 0.0041(16) 0.666(2) 0.0930(9) 0.049(4) Uiso d 0.1097(18) A 2
    D D20D -0.029537 0.579159 0.082990 0.074 Uiso calc 0.1097(18) A 2
    D D20E -0.012775 0.738825 0.047762 0.074 Uiso calc 0.1097(18) A 2
    D D20F 0.062047 0.641717 0.087819 0.074 Uiso calc 0.1097(18) A 2
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    S1A O6A . 1.5127(15) ?
    S1A C20A . 1.769(3) ?
    S1A C19A . 1.777(3) ?
    S1B O6B . 1.515(12) ?
    S1B C19B . 1.762(12) ?
    S1B C20B . 1.774(13) ?
    S5 C4A . 1.7407(17) ?
    S5 C5A . 1.7434(18) ?
    O1 C1 . 1.2288(19) ?
    O2 C11 . 1.207(2) ?
    O3 C11 . 1.322(2) ?
    O3 H3 . 0.8400 ?
    O4 C15 . 1.3692(19) ?
    O4 C18 . 1.433(2) ?
    O5A C4B . 1.338(3) ?
    O5A H5A . 0.8400 ?
    O5B C4C . 1.271(4) ?
    O5B H5B . 0.8400 ?
    N2 C1 . 1.362(2) ?
    N2 C12 . 1.419(2) ?
    N2 C3 . 1.479(2) ?
    C1 C10A . 1.511(2) ?
    C3A C4C . 1.521(2) ?
    C3A C4B . 1.521(2) ?
    C3A C10A . 1.521(2) ?
    C3A C3 . 1.532(2) ?
    C3A H3AA . 1.0000 ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    C4B C4A . 1.507(2) ?
    C4B H4A . 1.0000 ?
    C4C C4A . 1.507(2) ?
    C4C H4B . 1.0000 ?
    C4A C9B . 1.361(2) ?
    C5A C6 . 1.396(3) ?
    C5A C9A . 1.404(2) ?
    C6 C7 . 1.375(3) ?
    C6 H6A . 0.9500 ?
    C7 C8 . 1.401(3) ?
    C7 H7A . 0.9500 ?
    C8 C9 . 1.386(2) ?
    C8 H8A . 0.9500 ?
    C9B C9A . 1.441(2) ?
    C9B C10 . 1.507(2) ?
    C9A C9 . 1.400(2) ?
    C9 H9A . 0.9500 ?
    C10A C10 . 1.526(2) ?
    C10A H10A . 1.0000 ?
    C10 C11 . 1.527(2) ?
    C10 H10B . 1.0000 ?
    C12 C13 . 1.392(2) ?
    C12 C17 . 1.393(2) ?
    C13 C14 . 1.385(2) ?
    C13 H13A . 0.9500 ?
    C14 C15 . 1.393(2) ?
    C14 H14A . 0.9500 ?
    C15 C16 . 1.388(2) ?
    C16 C17 . 1.387(2) ?
    C16 H16A . 0.9500 ?
    C17 H17A . 0.9500 ?
    C18 H18A . 0.9800 ?
    C18 H18B . 0.9800 ?
    C18 H18C . 0.9800 ?
    C19A D19A . 0.9800 ?
    C19A D19B . 0.9800 ?
    C19A D19C . 0.9800 ?
    C20A D20A . 0.9800 ?
    C20A D20B . 0.9800 ?
    C20A D20C . 0.9800 ?
    C19B D19D . 0.9800 ?
    C19B D19E . 0.9800 ?
    C19B D19F . 0.9800 ?
    C20B D20D . 0.9800 ?
    C20B D20E . 0.9800 ?
    C20B D20F . 0.9800 ?
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
    O6A S1A C20A . . 106.26(13) ?
    O6A S1A C19A . . 104.20(12) ?
    C20A S1A C19A . . 99.03(13) ?
    O6B S1B C19B . . 105.6(8) ?
    O6B S1B C20B . . 105.2(8) ?
    C19B S1B C20B . . 100.2(9) ?
    C4A S5 C5A . . 91.61(8) ?
    C11 O3 H3 . . 109.5 ?
    C15 O4 C18 . . 116.77(13) ?
    C4B O5A H5A . . 109.5 ?
    C4C O5B H5B . . 109.5 ?
    C1 N2 C12 . . 125.06(13) ?
    C1 N2 C3 . . 112.06(13) ?
    C12 N2 C3 . . 122.38(13) ?
    O1 C1 N2 . . 127.11(15) ?
    O1 C1 C10A . . 125.25(14) ?
    N2 C1 C10A . . 107.58(13) ?
    C4C C3A C10A . . 108.91(14) ?
    C4B C3A C10A . . 108.91(14) ?
    C4C C3A C3 . . 119.35(13) ?
    C4B C3A C3 . . 119.35(13) ?
    C10A C3A C3 . . 102.18(12) ?
    C4B C3A H3AA . . 108.6 ?
    C10A C3A H3AA . . 108.6 ?
    C3 C3A H3AA . . 108.6 ?
    N2 C3 C3A . . 101.83(12) ?
    N2 C3 H3A . . 111.4 ?
    C3A C3 H3A . . 111.4 ?
    N2 C3 H3B . . 111.4 ?
    C3A C3 H3B . . 111.4 ?
    H3A C3 H3B . . 109.3 ?
    O5A C4B C4A . . 108.46(16) ?
    O5A C4B C3A . . 118.61(19) ?
    C4A C4B C3A . . 106.60(13) ?
    O5A C4B H4A . . 107.6 ?
    C4A C4B H4A . . 107.6 ?
    C3A C4B H4A . . 107.6 ?
    O5B C4C C4A . . 116.3(2) ?
    O5B C4C C3A . . 112.9(2) ?
    C4A C4C C3A . . 106.60(13) ?
    O5B C4C H4B . . 106.9 ?
    C4A C4C H4B . . 106.9 ?
    C3A C4C H4B . . 106.9 ?
    C9B C4A C4C . . 126.63(15) ?
    C9B C4A C4B . . 126.63(15) ?
    C9B C4A S5 . . 112.36(13) ?
    C4C C4A S5 . . 120.99(12) ?
    C4B C4A S5 . . 120.99(12) ?
    C6 C5A C9A . . 121.61(17) ?
    C6 C5A S5 . . 127.31(14) ?
    C9A C5A S5 . . 111.07(13) ?
    C7 C6 C5A . . 118.33(17) ?
    C7 C6 H6A . . 120.8 ?
    C5A C6 H6A . . 120.8 ?
    C6 C7 C8 . . 121.20(17) ?
    C6 C7 H7A . . 119.4 ?
    C8 C7 H7A . . 119.4 ?
    C9 C8 C7 . . 120.31(17) ?
    C9 C8 H8A . . 119.8 ?
    C7 C8 H8A . . 119.8 ?
    C4A C9B C9A . . 113.02(14) ?
    C4A C9B C10 . . 123.29(14) ?
    C9A C9B C10 . . 123.65(14) ?
    C9 C9A C5A . . 118.92(15) ?
    C9 C9A C9B . . 129.13(15) ?
    C5A C9A C9B . . 111.94(15) ?
    C8 C9 C9A . . 119.61(16) ?
    C8 C9 H9A . . 120.2 ?
    C9A C9 H9A . . 120.2 ?
    C1 C10A C3A . . 103.55(12) ?
    C1 C10A C10 . . 118.36(12) ?
    C3A C10A C10 . . 113.66(13) ?
    C1 C10A H10A . . 106.9 ?
    C3A C10A H10A . . 106.9 ?
    C10 C10A H10A . . 106.9 ?
    C9B C10 C10A . . 106.90(12) ?
    C9B C10 C11 . . 111.15(13) ?
    C10A C10 C11 . . 112.76(13) ?
    C9B C10 H10B . . 108.6 ?
    C10A C10 H10B . . 108.6 ?
    C11 C10 H10B . . 108.6 ?
    O2 C11 O3 . . 124.33(15) ?
    O2 C11 C10 . . 123.87(15) ?
    O3 C11 C10 . . 111.81(14) ?
    C13 C12 C17 . . 118.87(14) ?
    C13 C12 N2 . . 120.50(14) ?
    C17 C12 N2 . . 120.62(13) ?
    C14 C13 C12 . . 120.51(15) ?
    C14 C13 H13A . . 119.7 ?
    C12 C13 H13A . . 119.7 ?
    C13 C14 C15 . . 120.25(14) ?
    C13 C14 H14A . . 119.9 ?
    C15 C14 H14A . . 119.9 ?
    O4 C15 C16 . . 124.11(15) ?
    O4 C15 C14 . . 116.36(14) ?
    C16 C15 C14 . . 119.51(14) ?
    C17 C16 C15 . . 120.02(15) ?
    C17 C16 H16A . . 120.0 ?
    C15 C16 H16A . . 120.0 ?
    C16 C17 C12 . . 120.76(14) ?
    C16 C17 H17A . . 119.6 ?
    C12 C17 H17A . . 119.6 ?
    O4 C18 H18A . . 109.5 ?
    O4 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    O4 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
    S1A C19A D19A . . 109.5 ?
    S1A C19A D19B . . 109.5 ?
    D19A C19A D19B . . 109.5 ?
    S1A C19A D19C . . 109.5 ?
    D19A C19A D19C . . 109.5 ?
    D19B C19A D19C . . 109.5 ?
    S1A C20A D20A . . 109.5 ?
    S1A C20A D20B . . 109.5 ?
    D20A C20A D20B . . 109.5 ?
    S1A C20A D20C . . 109.5 ?
    D20A C20A D20C . . 109.5 ?
    D20B C20A D20C . . 109.5 ?
    S1B C19B D19D . . 109.5 ?
    S1B C19B D19E . . 109.5 ?
    D19D C19B D19E . . 109.5 ?
    S1B C19B D19F . . 109.5 ?
    D19D C19B D19F . . 109.5 ?
    D19E C19B D19F . . 109.5 ?
    S1B C20B D20D . . 109.5 ?
    S1B C20B D20E . . 109.5 ?
    D20D C20B D20E . . 109.5 ?
    S1B C20B D20F . . 109.5 ?
    D20D C20B D20F . . 109.5 ?
    D20E C20B D20F . . 109.5 ?
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
    C12 N2 C1 O1 . . . . 3.3(3) ?
    C3 N2 C1 O1 . . . . 175.30(16) ?
    C12 N2 C1 C10A . . . . -174.00(13) ?
    C3 N2 C1 C10A . . . . -1.96(18) ?
    C1 N2 C3 C3A . . . . 23.14(17) ?
    C12 N2 C3 C3A . . . . -164.58(14) ?
    C4C C3A C3 N2 . . . . -154.00(15) ?
    C4B C3A C3 N2 . . . . -154.00(15) ?
    C10A C3A C3 N2 . . . . -33.89(15) ?
    C10A C3A C4B O5A . . . . 172.66(17) ?
    C3 C3A C4B O5A . . . . -70.7(2) ?
    C10A C3A C4B C4A . . . . 50.03(19) ?
    C3 C3A C4B C4A . . . . 166.67(15) ?
    C10A C3A C4C O5B . . . . -78.8(2) ?
    C3 C3A C4C O5B . . . . 37.8(3) ?
    C10A C3A C4C C4A . . . . 50.03(19) ?
    C3 C3A C4C C4A . . . . 166.67(15) ?
    O5B C4C C4A C9B . . . . 107.8(3) ?
    C3A C4C C4A C9B . . . . -19.0(3) ?
    O5B C4C C4A S5 . . . . -70.3(3) ?
    C3A C4C C4A S5 . . . . 162.82(13) ?
    O5A C4B C4A C9B . . . . -147.8(2) ?
    C3A C4B C4A C9B . . . . -19.0(3) ?
    O5A C4B C4A S5 . . . . 34.0(2) ?
    C3A C4B C4A S5 . . . . 162.82(13) ?
    C5A S5 C4A C9B . . . . 0.01(15) ?
    C5A S5 C4A C4C . . . . 178.43(16) ?
    C5A S5 C4A C4B . . . . 178.43(16) ?
    C4A S5 C5A C6 . . . . -179.43(19) ?
    C4A S5 C5A C9A . . . . -0.33(14) ?
    C9A C5A C6 C7 . . . . -0.2(3) ?
    S5 C5A C6 C7 . . . . 178.84(16) ?
    C5A C6 C7 C8 . . . . -0.9(3) ?
    C6 C7 C8 C9 . . . . 1.4(3) ?
    C4C C4A C9B C9A . . . . -178.00(17) ?
    C4B C4A C9B C9A . . . . -178.00(17) ?
    S5 C4A C9B C9A . . . . 0.3(2) ?
    C4C C4A C9B C10 . . . . -0.4(3) ?
    C4B C4A C9B C10 . . . . -0.4(3) ?
    S5 C4A C9B C10 . . . . 177.93(13) ?
    C6 C5A C9A C9 . . . . 0.8(3) ?
    S5 C5A C9A C9 . . . . -178.38(13) ?
    C6 C5A C9A C9B . . . . 179.71(17) ?
    S5 C5A C9A C9B . . . . 0.55(19) ?
    C4A C9B C9A C9 . . . . 178.24(17) ?
    C10 C9B C9A C9 . . . . 0.6(3) ?
    C4A C9B C9A C5A . . . . -0.6(2) ?
    C10 C9B C9A C5A . . . . -178.18(15) ?
    C7 C8 C9 C9A . . . . -0.8(3) ?
    C5A C9A C9 C8 . . . . -0.3(2) ?
    C9B C9A C9 C8 . . . . -179.02(17) ?
    O1 C1 C10A C3A . . . . 162.34(16) ?
    N2 C1 C10A C3A . . . . -20.34(16) ?
    O1 C1 C10A C10 . . . . 35.5(2) ?
    N2 C1 C10A C10 . . . . -147.14(14) ?
    C4C C3A C10A C1 . . . . 160.51(13) ?
    C4B C3A C10A C1 . . . . 160.51(13) ?
    C3 C3A C10A C1 . . . . 33.35(15) ?
    C4C C3A C10A C10 . . . . -69.78(17) ?
    C4B C3A C10A C10 . . . . -69.78(17) ?
    C3 C3A C10A C10 . . . . 163.06(13) ?
    C4A C9B C10 C10A . . . . -12.4(2) ?
    C9A C9B C10 C10A . . . . 165.01(14) ?
    C4A C9B C10 C11 . . . . 111.08(18) ?
    C9A C9B C10 C11 . . . . -71.54(19) ?
    C1 C10A C10 C9B . . . . 168.32(13) ?
    C3A C10A C10 C9B . . . . 46.52(17) ?
    C1 C10A C10 C11 . . . . 45.88(19) ?
    C3A C10A C10 C11 . . . . -75.93(17) ?
    C9B C10 C11 O2 . . . . -57.9(2) ?
    C10A C10 C11 O2 . . . . 62.1(2) ?
    C9B C10 C11 O3 . . . . 122.07(15) ?
    C10A C10 C11 O3 . . . . -117.90(15) ?
    C1 N2 C12 C13 . . . . 152.25(16) ?
    C3 N2 C12 C13 . . . . -19.0(2) ?
    C1 N2 C12 C17 . . . . -28.8(2) ?
    C3 N2 C12 C17 . . . . 159.92(15) ?
    C17 C12 C13 C14 . . . . 1.0(2) ?
    N2 C12 C13 C14 . . . . 179.89(15) ?
    C12 C13 C14 C15 . . . . 1.6(2) ?
    C18 O4 C15 C16 . . . . 4.1(2) ?
    C18 O4 C15 C14 . . . . -177.49(15) ?
    C13 C14 C15 O4 . . . . 178.70(15) ?
    C13 C14 C15 C16 . . . . -2.8(2) ?
    O4 C15 C16 C17 . . . . 179.86(15) ?
    C14 C15 C16 C17 . . . . 1.5(2) ?
    C15 C16 C17 C12 . . . . 1.1(2) ?
    C13 C12 C17 C16 . . . . -2.3(2) ?
    N2 C12 C17 C16 . . . . 178.78(15) ?
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
    O3 H3 S1A . 0.8400 2.7200 3.4846(15) 152.00 yes
    O3 H3 O6A . 0.8400 1.7200 2.563(2) 176.00 yes
    O3 H3 O6B . 0.8400 2.0600 2.852(16) 158.00 yes
    O5A H5A O1 4_576 0.8400 1.9600 2.763(2) 160.00 yes
    C3A H3AA O2 . 1.0000 2.4900 3.202(2) 127.00 yes
    C3 H3A O5B . 0.9900 2.5400 2.887(4) 100.00 yes
    C6 H6A O6A 4_586 0.9500 2.4800 3.307(3) 145.00 yes
    C14 H14A O4 3_656 0.9500 2.5400 3.445(2) 159.00 yes
    C17 H17A O1 . 0.9500 2.3300 2.868(2) 116.00 yes
    C17 H17A O5B 4_575 0.9500 2.4600 3.289(4) 146.00 yes
    C18 H18C O5B 3_666 0.9800 2.4300 2.922(4) 110.00 yes
    C20A D20A O6A 2_545 0.9800 2.4600 3.434(3) 173.00 yes
    C20A D20A O6B 2_545 0.9800 1.8700 2.839(13) 168.00 yes
_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     0.896
_shelx_estimated_absorpt_T_max     0.941
