##############################################################################
#                                                                            #
# 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-2017/1'
_journal_date_recd_electronic     2024-01-16
_journal_date_accepted     2024-02-08
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2024
_journal_volume     80
_journal_issue      3
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989024001300
_journal_coeditor_code     DX2059
_publ_contact_author_name     'Artur Sikorski'
_publ_contact_author_address
;
Faculty of Chemistry
University of Gdańsk
W. Stwosza 63
80-308 Gdańsk
Poland
;
_publ_contact_author_email     artur.sikorski@ug.edu.pl
_publ_contact_author_fax     '+48 58 523 5010'
_publ_contact_author_phone     '+48 58 523 5112'
_publ_section_title
;
Crystal structure of the tetraethylammonium salt of the non-steroidal
anti-inflammatory drug nimesulide (polymorph II)
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Rybczyńska, Małgorzata' .
;
Faculty of Chemistry
University of Gdańsk
W. Stwosza 63
80-308 Gdańsk
Poland
;
    'Sikorski, Artur' .
;
Faculty of Chemistry
University of Gdańsk
W. Stwosza 63
80-308 Gdańsk
Poland
;
_publ_section_synopsis
;
The crystal structure of the tetraethylammonium salt of the non-steroidal
anti-inflammatory drug nimesulide (polymorph II),
C₈H₂₀N⁺\\cdotC₁₃H₁₁N₂O₅S⁻, was determined using single-crystal
X-ray diffraction. There are differences in the geometry of both the
nimesulide anion and the tetraethylammonium cation in polymorphs I and II of
the title compound.
;
_chemical_name_systematic
;
Tetraethylammonium N-methanesulfonyl-4-nitro-2-phenoxyanilinide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C8 H20 N +, C13 H11 N2 O5 S -'
_chemical_formula_sum     'C21 H31 N3 O5 S'
_chemical_formula_iupac     'C8 H20 N +, C13 H11 N2 O5 S -'
_chemical_formula_weight     437.55
_chemical_melting_point     388
_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     11.0276(10)
_cell_length_b     10.7661(8)
_cell_length_c     19.635(2)
_cell_angle_alpha     90
_cell_angle_beta     91.792(9)
_cell_angle_gamma     90
_cell_volume     2330.0(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     15531
_cell_measurement_theta_min     3.327
_cell_measurement_theta_max     25.002
_cell_measurement_temperature     291(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.420
_exptl_crystal_size_mid     0.200
_exptl_crystal_size_min     0.090
_exptl_crystal_density_diffrn     1.247
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     936
_exptl_absorpt_coefficient_mu     0.174
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2008).
;
_exptl_absorpt_correction_T_min     0.966
_exptl_absorpt_correction_T_max     0.998
_diffrn_ambient_temperature     291(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Oxford Diffraction Ruby CCD'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     10.4002
_diffrn_reflns_number     15531
_diffrn_reflns_av_R_equivalents     0.0727
_diffrn_reflns_av_unetI/netI     0.0796
_diffrn_reflns_theta_min     3.327
_diffrn_reflns_theta_max     25.002
_diffrn_reflns_theta_full     25.002
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -23
_diffrn_reflns_limit_l_max     23
_refine_special_details     ?
_reflns_number_total     4094
_reflns_number_gt     2549
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1210
_refine_ls_R_factor_gt     0.0657
_refine_ls_wR_factor_gt     0.1074
_refine_ls_wR_factor_ref     0.1277
_refine_ls_goodness_of_fit_ref     1.097
_refine_ls_restrained_S_all     1.097
_refine_ls_number_reflns     4094
_refine_ls_number_parameters     276
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0316P)²+0.0136P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.161
_refine_diff_density_min     -0.229
_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'
    '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
;
CrysAlis CCD Version 1.171.32.15 (Oxford Diffraction, 2008)
;
_computing_cell_refinement
;
CrysAlis RED Version 1.171.32.15 (Oxford Diffraction, 2008)
;
_computing_data_reduction
;
CrysAlis RED Version 1.171.32.15 (Oxford Diffraction, 2008)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2017/1 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
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
    N N22 0.8646(2) 0.6786(2) 0.66998(12) 0.0466(7) Uani d 1 . .
    C C23 0.7364(3) 0.6589(3) 0.6432(2) 0.0679(10) Uani d 1 . .
    H H23A 0.738581 0.638164 0.595204 0.082 Uiso calc 1 . .
    H H23B 0.692237 0.736376 0.647115 0.082 Uiso calc 1 . .
    C C24 0.6669(4) 0.5566(3) 0.6801(3) 0.1112(17) Uani d 1 . .
    H H24A 0.590665 0.541912 0.656474 0.167 Uiso calc 1 . .
    H H24B 0.652626 0.582332 0.725925 0.167 Uiso calc 1 . .
    H H24C 0.713924 0.481527 0.680791 0.167 Uiso calc 1 . .
    C C25 0.8677(4) 0.7082(3) 0.74529(16) 0.0678(10) Uani d 1 . .
    H H25A 0.951411 0.722287 0.759958 0.081 Uiso calc 1 . .
    H H25B 0.839097 0.636099 0.769643 0.081 Uiso calc 1 . .
    C C26 0.7934(4) 0.8196(3) 0.76588(18) 0.0801(12) Uani d 1 . .
    H H26A 0.804123 0.833377 0.814002 0.120 Uiso calc 1 . .
    H H26B 0.709188 0.804419 0.755044 0.120 Uiso calc 1 . .
    H H26C 0.819681 0.891737 0.741652 0.120 Uiso calc 1 . .
    C C27 0.9144(3) 0.7874(3) 0.63015(17) 0.0609(10) Uani d 1 . .
    H H27A 0.905286 0.768693 0.581930 0.073 Uiso calc 1 . .
    H H27B 0.865104 0.859849 0.638968 0.073 Uiso calc 1 . .
    C C28 1.0453(4) 0.8203(3) 0.6455(2) 0.0968(15) Uani d 1 . .
    H H28A 1.064308 0.897193 0.623559 0.145 Uiso calc 1 . .
    H H28B 1.096702 0.755682 0.628966 0.145 Uiso calc 1 . .
    H H28C 1.058343 0.828854 0.693876 0.145 Uiso calc 1 . .
    C C29 0.9416(3) 0.5635(3) 0.66162(18) 0.0599(9) Uani d 1 . .
    H H29A 1.021525 0.579523 0.681782 0.072 Uiso calc 1 . .
    H H29B 0.905901 0.496372 0.687120 0.072 Uiso calc 1 . .
    C C30 0.9563(4) 0.5207(3) 0.58923(19) 0.0810(12) Uani d 1 . .
    H H30A 1.002975 0.445354 0.589154 0.122 Uiso calc 1 . .
    H H30B 0.997549 0.583607 0.564185 0.122 Uiso calc 1 . .
    H H30C 0.877894 0.505702 0.568264 0.122 Uiso calc 1 . .
    C C1 0.5837(3) 0.1058(3) 0.62935(14) 0.0395(7) Uani d 1 . .
    C C2 0.4877(3) 0.0172(3) 0.62920(15) 0.0435(8) Uani d 1 . .
    C C3 0.3730(3) 0.0461(3) 0.60651(15) 0.0487(8) Uani d 1 . .
    H H3A 0.312492 -0.014135 0.605923 0.058 Uiso calc 1 . .
    C C4 0.3469(3) 0.1659(3) 0.58428(15) 0.0443(8) Uani d 1 . .
    C C5 0.4352(3) 0.2565(3) 0.58697(16) 0.0508(9) Uani d 1 . .
    H H5A 0.416335 0.337348 0.573719 0.061 Uiso calc 1 . .
    C C6 0.5507(3) 0.2275(3) 0.60917(15) 0.0482(8) Uani d 1 . .
    H H6A 0.609174 0.289699 0.611006 0.058 Uiso calc 1 . .
    N N7 0.6961(2) 0.0639(2) 0.64924(12) 0.0463(7) Uani d 1 . .
    S S8 0.81473(7) 0.14575(7) 0.64359(4) 0.0480(2) Uani d 1 . .
    O O9 0.9111(2) 0.07799(19) 0.67799(12) 0.0651(7) Uani d 1 . .
    O O10 0.8031(2) 0.27336(18) 0.66560(12) 0.0650(7) Uani d 1 . .
    C C11 0.8486(3) 0.1503(3) 0.55687(17) 0.0700(10) Uani d 1 . .
    H H11A 0.923935 0.193215 0.551381 0.105 Uiso calc 1 . .
    H H11B 0.784964 0.192962 0.531955 0.105 Uiso calc 1 . .
    H H11C 0.855381 0.067033 0.539846 0.105 Uiso calc 1 . .
    O O12 0.5189(2) -0.09796(19) 0.65561(12) 0.0652(7) Uani d 1 . .
    C C13 0.4449(3) -0.2003(3) 0.63959(18) 0.0470(8) Uani d 1 . .
    C C14 0.4353(3) -0.2436(3) 0.57443(18) 0.0627(10) Uani d 1 . .
    H H14A 0.471834 -0.201598 0.539124 0.075 Uiso calc 1 . .
    C C15 0.3699(3) -0.3516(3) 0.56192(18) 0.0666(10) Uani d 1 . .
    H H15A 0.362559 -0.382462 0.517737 0.080 Uiso calc 1 . .
    C C16 0.3162(3) -0.4132(3) 0.6137(2) 0.0615(10) Uani d 1 . .
    H H16A 0.272162 -0.485449 0.604827 0.074 Uiso calc 1 . .
    C C17 0.3275(3) -0.3681(3) 0.6785(2) 0.0681(11) Uani d 1 . .
    H H17A 0.291625 -0.410340 0.713952 0.082 Uiso calc 1 . .
    C C18 0.3917(3) -0.2604(3) 0.69191(17) 0.0583(9) Uani d 1 . .
    H H18A 0.398465 -0.229272 0.736042 0.070 Uiso calc 1 . .
    N N19 0.2270(3) 0.1945(3) 0.55838(14) 0.0586(8) Uani d 1 . .
    O O20 0.1507(2) 0.1114(3) 0.55356(16) 0.0935(9) Uani d 1 . .
    O O21 0.2031(2) 0.3022(2) 0.54080(13) 0.0770(8) Uani d 1 . .
_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
    N22 C23 . 1.508(4) ?
    N22 C25 . 1.512(4) ?
    N22 C29 . 1.514(3) ?
    N22 C27 . 1.520(4) ?
    C23 C24 . 1.536(5) ?
    C23 H23A . 0.9700 ?
    C23 H23B . 0.9700 ?
    C24 H24A . 0.9600 ?
    C24 H24B . 0.9600 ?
    C24 H24C . 0.9600 ?
    C25 C26 . 1.515(4) ?
    C25 H25A . 0.9700 ?
    C25 H25B . 0.9700 ?
    C26 H26A . 0.9600 ?
    C26 H26B . 0.9600 ?
    C26 H26C . 0.9600 ?
    C27 C28 . 1.508(5) ?
    C27 H27A . 0.9700 ?
    C27 H27B . 0.9700 ?
    C28 H28A . 0.9600 ?
    C28 H28B . 0.9600 ?
    C28 H28C . 0.9600 ?
    C29 C30 . 1.508(4) ?
    C29 H29A . 0.9700 ?
    C29 H29B . 0.9700 ?
    C30 H30A . 0.9600 ?
    C30 H30B . 0.9600 ?
    C30 H30C . 0.9600 ?
    C1 N7 . 1.365(4) ?
    C1 C6 . 1.412(4) ?
    C1 C2 . 1.425(4) ?
    C2 C3 . 1.364(4) ?
    C2 O12 . 1.383(3) ?
    C3 C4 . 1.389(4) ?
    C3 H3A . 0.9300 ?
    C4 C5 . 1.378(4) ?
    C4 N19 . 1.436(4) ?
    C5 C6 . 1.370(4) ?
    C5 H5A . 0.9300 ?
    C6 H6A . 0.9300 ?
    N7 S8 . 1.584(2) ?
    S8 O9 . 1.439(2) ?
    S8 O10 . 1.447(2) ?
    S8 C11 . 1.755(3) ?
    C11 H11A . 0.9600 ?
    C11 H11B . 0.9600 ?
    C11 H11C . 0.9600 ?
    O12 C13 . 1.401(3) ?
    C13 C14 . 1.363(4) ?
    C13 C18 . 1.363(4) ?
    C14 C15 . 1.387(5) ?
    C14 H14A . 0.9300 ?
    C15 C16 . 1.364(5) ?
    C15 H15A . 0.9300 ?
    C16 C17 . 1.365(5) ?
    C16 H16A . 0.9300 ?
    C17 C18 . 1.379(4) ?
    C17 H17A . 0.9300 ?
    C18 H18A . 0.9300 ?
    N19 O20 . 1.230(3) ?
    N19 O21 . 1.235(3) ?
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
    C23 N22 C25 . . 111.3(3) ?
    C23 N22 C29 . . 111.7(2) ?
    C25 N22 C29 . . 106.5(2) ?
    C23 N22 C27 . . 106.2(2) ?
    C25 N22 C27 . . 110.1(2) ?
    C29 N22 C27 . . 111.2(2) ?
    N22 C23 C24 . . 114.4(3) ?
    N22 C23 H23A . . 108.7 ?
    C24 C23 H23A . . 108.7 ?
    N22 C23 H23B . . 108.7 ?
    C24 C23 H23B . . 108.7 ?
    H23A C23 H23B . . 107.6 ?
    C23 C24 H24A . . 109.5 ?
    C23 C24 H24B . . 109.5 ?
    H24A C24 H24B . . 109.5 ?
    C23 C24 H24C . . 109.5 ?
    H24A C24 H24C . . 109.5 ?
    H24B C24 H24C . . 109.5 ?
    N22 C25 C26 . . 115.6(3) ?
    N22 C25 H25A . . 108.4 ?
    C26 C25 H25A . . 108.4 ?
    N22 C25 H25B . . 108.4 ?
    C26 C25 H25B . . 108.4 ?
    H25A C25 H25B . . 107.4 ?
    C25 C26 H26A . . 109.5 ?
    C25 C26 H26B . . 109.5 ?
    H26A C26 H26B . . 109.5 ?
    C25 C26 H26C . . 109.5 ?
    H26A C26 H26C . . 109.5 ?
    H26B C26 H26C . . 109.5 ?
    C28 C27 N22 . . 115.9(3) ?
    C28 C27 H27A . . 108.3 ?
    N22 C27 H27A . . 108.3 ?
    C28 C27 H27B . . 108.3 ?
    N22 C27 H27B . . 108.3 ?
    H27A C27 H27B . . 107.4 ?
    C27 C28 H28A . . 109.5 ?
    C27 C28 H28B . . 109.5 ?
    H28A C28 H28B . . 109.5 ?
    C27 C28 H28C . . 109.5 ?
    H28A C28 H28C . . 109.5 ?
    H28B C28 H28C . . 109.5 ?
    C30 C29 N22 . . 115.5(3) ?
    C30 C29 H29A . . 108.4 ?
    N22 C29 H29A . . 108.4 ?
    C30 C29 H29B . . 108.4 ?
    N22 C29 H29B . . 108.4 ?
    H29A C29 H29B . . 107.5 ?
    C29 C30 H30A . . 109.5 ?
    C29 C30 H30B . . 109.5 ?
    H30A C30 H30B . . 109.5 ?
    C29 C30 H30C . . 109.5 ?
    H30A C30 H30C . . 109.5 ?
    H30B C30 H30C . . 109.5 ?
    N7 C1 C6 . . 127.6(3) ?
    N7 C1 C2 . . 116.6(3) ?
    C6 C1 C2 . . 115.8(3) ?
    C3 C2 O12 . . 123.0(3) ?
    C3 C2 C1 . . 122.0(3) ?
    O12 C2 C1 . . 115.0(3) ?
    C2 C3 C4 . . 119.7(3) ?
    C2 C3 H3A . . 120.2 ?
    C4 C3 H3A . . 120.2 ?
    C5 C4 C3 . . 120.4(3) ?
    C5 C4 N19 . . 120.2(3) ?
    C3 C4 N19 . . 119.4(3) ?
    C6 C5 C4 . . 120.0(3) ?
    C6 C5 H5A . . 120.0 ?
    C4 C5 H5A . . 120.0 ?
    C5 C6 C1 . . 122.0(3) ?
    C5 C6 H6A . . 119.0 ?
    C1 C6 H6A . . 119.0 ?
    C1 N7 S8 . . 122.7(2) ?
    O9 S8 O10 . . 114.35(14) ?
    O9 S8 N7 . . 106.51(13) ?
    O10 S8 N7 . . 115.20(13) ?
    O9 S8 C11 . . 107.03(16) ?
    O10 S8 C11 . . 106.68(16) ?
    N7 S8 C11 . . 106.53(16) ?
    S8 C11 H11A . . 109.5 ?
    S8 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    S8 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    C2 O12 C13 . . 119.0(2) ?
    C14 C13 C18 . . 121.5(3) ?
    C14 C13 O12 . . 120.5(3) ?
    C18 C13 O12 . . 117.8(3) ?
    C13 C14 C15 . . 118.6(3) ?
    C13 C14 H14A . . 120.7 ?
    C15 C14 H14A . . 120.7 ?
    C16 C15 C14 . . 120.8(3) ?
    C16 C15 H15A . . 119.6 ?
    C14 C15 H15A . . 119.6 ?
    C15 C16 C17 . . 119.5(3) ?
    C15 C16 H16A . . 120.2 ?
    C17 C16 H16A . . 120.2 ?
    C16 C17 C18 . . 120.6(3) ?
    C16 C17 H17A . . 119.7 ?
    C18 C17 H17A . . 119.7 ?
    C13 C18 C17 . . 119.1(3) ?
    C13 C18 H18A . . 120.5 ?
    C17 C18 H18A . . 120.5 ?
    O20 N19 O21 . . 121.5(3) ?
    O20 N19 C4 . . 119.4(3) ?
    O21 N19 C4 . . 119.1(3) ?
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
    C25 N22 C23 C24 . . . . -57.0(4) ?
    C29 N22 C23 C24 . . . . 61.9(4) ?
    C27 N22 C23 C24 . . . . -176.7(3) ?
    C23 N22 C25 C26 . . . . -56.6(4) ?
    C29 N22 C25 C26 . . . . -178.6(3) ?
    C27 N22 C25 C26 . . . . 60.8(4) ?
    C23 N22 C27 C28 . . . . -176.8(3) ?
    C25 N22 C27 C28 . . . . 62.7(4) ?
    C29 N22 C27 C28 . . . . -55.0(4) ?
    C23 N22 C29 C30 . . . . 61.3(4) ?
    C25 N22 C29 C30 . . . . -177.1(3) ?
    C27 N22 C29 C30 . . . . -57.2(4) ?
    N7 C1 C2 C3 . . . . -176.0(3) ?
    C6 C1 C2 C3 . . . . 4.3(4) ?
    N7 C1 C2 O12 . . . . 5.9(4) ?
    C6 C1 C2 O12 . . . . -173.7(3) ?
    O12 C2 C3 C4 . . . . 176.3(3) ?
    C1 C2 C3 C4 . . . . -1.6(5) ?
    C2 C3 C4 C5 . . . . -2.0(4) ?
    C2 C3 C4 N19 . . . . 178.0(3) ?
    C3 C4 C5 C6 . . . . 2.6(5) ?
    N19 C4 C5 C6 . . . . -177.4(3) ?
    C4 C5 C6 C1 . . . . 0.4(5) ?
    N7 C1 C6 C5 . . . . 176.7(3) ?
    C2 C1 C6 C5 . . . . -3.8(4) ?
    C6 C1 N7 S8 . . . . -8.2(4) ?
    C2 C1 N7 S8 . . . . 172.3(2) ?
    C1 N7 S8 O9 . . . . 172.0(2) ?
    C1 N7 S8 O10 . . . . 44.0(3) ?
    C1 N7 S8 C11 . . . . -74.0(3) ?
    C3 C2 O12 C13 . . . . 20.9(4) ?
    C1 C2 O12 C13 . . . . -161.0(3) ?
    C2 O12 C13 C14 . . . . 66.3(4) ?
    C2 O12 C13 C18 . . . . -118.9(3) ?
    C18 C13 C14 C15 . . . . -0.2(5) ?
    O12 C13 C14 C15 . . . . 174.3(3) ?
    C13 C14 C15 C16 . . . . 0.1(5) ?
    C14 C15 C16 C17 . . . . -0.3(6) ?
    C15 C16 C17 C18 . . . . 0.6(6) ?
    C14 C13 C18 C17 . . . . 0.6(5) ?
    O12 C13 C18 C17 . . . . -174.1(3) ?
    C16 C17 C18 C13 . . . . -0.8(5) ?
    C5 C4 N19 O20 . . . . 176.9(3) ?
    C3 C4 N19 O20 . . . . -3.1(4) ?
    C5 C4 N19 O21 . . . . -2.4(4) ?
    C3 C4 N19 O21 . . . . 177.6(3) ?
loop_
    _geom_hbond_atom_site_label_d
    _geom_hbond_atom_site_label_h
    _geom_hbond_atom_site_label_a
    _geom_hbond_site_symmetry_d
    _geom_hbond_site_symmetry_h
    _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
    C11 H11A O20 1_555 1_555 1_655 0.96 2.65 3.360(4) 131 yes
    C11 H11C O20 1_555 1_555 3_656 0.96 2.66 3.555(4) 156 yes
    C17 H17A N7 1_555 1_555 2_646 0.93 2.70 3.478(4) 142 yes
    C24 H24C O10 1_555 1_555 1_555 0.96 2.47 3.415(4) 168 yes
    C25 H25A O9 1_555 1_555 2_756 0.97 2.47 3.155(5) 128 yes
    C26 H26C O9 1_555 1_555 1_565 0.96 2.58 3.541(4) 175 yes
    C27 H27B O9 1_555 1_555 1_565 0.97 2.52 3.267(4) 134 yes
    C14 H14A Cg1 1_555 1_555 3_656 0.93 3.07 3.951(5) 158 yes
    C24 H24A Cg2 1_555 1_555 1_565 0.96 2.88 3.608(5) 134 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     0.930
_shelx_estimated_absorpt_T_max     0.985
