##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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 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. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     'SHELXL97 CIF, edited IUCr template'
_journal_date_recd_electronic     2010-03-10
_journal_date_accepted     2010-05-18
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      7
_journal_page_first     o1792
_journal_page_last     o1792
_journal_paper_category     QO
_journal_coeditor_code     FJ2286
_publ_contact_author_name     'Dr P.A. Crooks'
_publ_contact_author_address
;
Dept. of Pharm. Sciences
College of Pharmacy
University of Kentucky
Lexington
KY 40536
USA
;
_publ_contact_author_email     'pcrooks@email.uky.edu'
_publ_contact_author_fax     '859 257 2585'
_publ_contact_author_phone     '859 257 1718'
_publ_section_title
;\
(<i>Z</i>)-2-Amino-5-[2,4-dimethoxy-6-(4-methoxystyryl)benzylidene]-1,3-\
thiazol-4(5<i>H</i>)-one methanol solvate
;
loop_
    _publ_author_name
    _publ_author_address
    'Nikhil Reddy Madadi'
;
Department of Pharmaceutical Sciences
College of Pharmacy
University of Kentucky
Lexington
KY 40536
USA
;
    'Thirupathi Reddy Yerram Reddy'
;
Department of Pharmaceutical Sciences
College of Pharmacy
University of Kentucky
Lexington
KY 40536
USA
;
    'Narsimha Reddy Penthala'
;
Department of Pharmaceutical Sciences
College of Pharmacy
University of Kentucky
Lexington
KY 40536
USA
;
    'Parkin, Sean'
;
Department of Chemistry
University of Kentucky
Lexington
KY 40506
USA
;
    'Crooks, Peter A.'
;
Department of Pharmaceutical Sciences
College of Pharmacy
University of Kentucky
Lexington
KY 40536
USA
;
_refine_special_details
;
Refinement of F\^2\^ against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F\^2\^, conventional R-factors R are based
on F, with F set to zero for negative F\^2\^. The threshold expression of
F\^2\^ > 2\s(F\^2\^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F\^2\^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(<i>Z</i>)-2-Amino-5-[2,4-dimethoxy-6-(4-methoxystyryl)benzylidene]-1,3-
thiazol-4(5<i>H</i>)-one methanol solvate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C21 H20 N2 O4 S, C H4 O'
_chemical_formula_sum     'C22 H24 N2 O5 S'
_chemical_formula_iupac     'C21 H20 N2 O4 S, C H4 O'
_chemical_formula_weight     428.49
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     10.6243(2)
_cell_length_b     22.2530(5)
_cell_length_c     9.0562(2)
_cell_angle_alpha     90.00
_cell_angle_beta     93.0280(10)
_cell_angle_gamma     90.00
_cell_volume     2138.10(8)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9054
_cell_measurement_theta_min     3.97
_cell_measurement_theta_max     68.35
_cell_measurement_temperature     90.0(2)
_exptl_crystal_description     lath
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.15
_exptl_crystal_size_mid     0.08
_exptl_crystal_size_min     0.02
_exptl_crystal_density_diffrn     1.331
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     904
_exptl_absorpt_coefficient_mu     1.652
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2006)'
_exptl_absorpt_correction_T_min     0.777
_exptl_absorpt_correction_T_max     0.968
_exptl_special_details
;
;
_diffrn_ambient_temperature     90.0(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_source     'fine-focus rotating anode'
_diffrn_radiation_monochromator     'graded multilayer optics'
_diffrn_measurement_device_type     'Bruker X8 Proteum'
_diffrn_measurement_method     '\f and \w scans'
_diffrn_detector_area_resol_mean     5.6
_diffrn_reflns_number     31098
_diffrn_reflns_av_R_equivalents     0.0442
_diffrn_reflns_av_sigmaI/netI     0.0265
_diffrn_reflns_theta_min     3.97
_diffrn_reflns_theta_max     68.39
_diffrn_reflns_theta_full     68.39
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -26
_diffrn_reflns_limit_k_max     26
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     10
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted <i>R</i>-factor
wR and goodness of fit <i>S</i> are based on <i>F</i>^2^, conventional
<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
negative <i>F</i>^2^. The threshold expression of <i>F</i>^2^ >
2\s(<i>F</i>^2^) is used only for calculating <i>R</i>-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. <i>R</i>-factors
based on <i>F</i>^2^ are statistically about twice as large as those based on
<i>F</i>, and <i>R</i>- factors based on ALL data will be even larger.
;
_reflns_number_total     3911
_reflns_number_gt     3631
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0462
_refine_ls_R_factor_gt     0.0430
_refine_ls_wR_factor_gt     0.1098
_refine_ls_wR_factor_ref     0.1122
_refine_ls_goodness_of_fit_ref     1.129
_refine_ls_restrained_S_all     1.129
_refine_ls_number_reflns     3911
_refine_ls_number_parameters     276
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0357P)^2^+2.3067P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.511
_refine_diff_density_min     -0.300
_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' 0.0181 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'
    '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'
_computing_data_collection     'APEX2 (Bruker, 2006)'
_computing_cell_refinement     'SAINT (Bruker, 2006)'
_computing_data_reduction     'SAINT (Bruker, 2006)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and local procedures
;
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_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.73380(5) 0.59495(2) 0.83763(5) 0.02575(15) Uani d . 1 . .
    O O1 0.84106(14) 0.45171(6) 0.46089(17) 0.0294(3) Uani d . 1 . .
    N N1 0.79198(16) 0.69625(7) 0.70367(18) 0.0233(4) Uani d . 1 . .
    C C1 0.67303(19) 0.48654(9) 0.5941(2) 0.0230(4) Uani d . 1 . .
    O O2 0.56944(16) 0.31027(7) 0.6733(2) 0.0401(4) Uani d . 1 . .
    N N2 0.78786(18) 0.70133(8) 0.95934(19) 0.0288(4) Uani d . 1 . .
    H H2A 0.8067 0.7398 0.9591 0.035 Uiso calc R 1 . .
    H H2B 0.7766 0.6828 1.0435 0.035 Uiso calc R 1 . .
    C C2 0.73882(19) 0.43671(9) 0.5382(2) 0.0247(4) Uani d . 1 . .
    O O3 0.15908(16) 0.72923(7) 1.04700(19) 0.0379(4) Uani d . 1 . .
    C C3 0.7014(2) 0.37874(9) 0.5646(2) 0.0287(5) Uani d . 1 . .
    H H3 0.7459 0.3457 0.5260 0.034 Uiso calc R 1 . .
    O O4 0.79309(15) 0.66720(6) 0.46217(15) 0.0276(3) Uani d . 1 . .
    C C4 0.5968(2) 0.36913(9) 0.6495(2) 0.0285(5) Uani d . 1 . .
    C C5 0.5283(2) 0.41643(9) 0.7024(2) 0.0254(4) Uani d . 1 . .
    H H5 0.4560 0.4090 0.7571 0.031 Uiso calc R 1 . .
    C C6 0.56614(19) 0.47574(9) 0.6748(2) 0.0227(4) Uani d . 1 . .
    C C7 0.49002(19) 0.52638(9) 0.7237(2) 0.0230(4) Uani d . 1 . .
    H H7 0.4958 0.5629 0.6702 0.028 Uiso calc R 1 . .
    C C8 0.41358(19) 0.52599(9) 0.8360(2) 0.0252(4) Uani d . 1 . .
    H H8 0.4032 0.4890 0.8861 0.030 Uiso calc R 1 . .
    C C9 0.34427(19) 0.57835(9) 0.8881(2) 0.0249(4) Uani d . 1 . .
    C C10 0.2585(2) 0.57198(10) 0.9977(2) 0.0280(5) Uani d . 1 . .
    H H10 0.2434 0.5330 1.0359 0.034 Uiso calc R 1 . .
    C C11 0.1938(2) 0.62079(10) 1.0535(2) 0.0296(5) Uani d . 1 . .
    H H11 0.1356 0.6150 1.1283 0.036 Uiso calc R 1 . .
    C C12 0.2153(2) 0.67762(10) 0.9992(2) 0.0296(5) Uani d . 1 . .
    C C13 0.2998(2) 0.68532(10) 0.8890(3) 0.0363(5) Uani d . 1 . .
    H H13 0.3138 0.7243 0.8502 0.044 Uiso calc R 1 . .
    C C14 0.3634(2) 0.63662(10) 0.8357(3) 0.0325(5) Uani d . 1 . .
    H H14 0.4219 0.6428 0.7614 0.039 Uiso calc R 1 . .
    C C15 0.71662(18) 0.54678(9) 0.5548(2) 0.0223(4) Uani d . 1 . .
    H H15 0.7306 0.5531 0.4533 0.027 Uiso calc R 1 . .
    C C16 0.73910(19) 0.59395(9) 0.6445(2) 0.0224(4) Uani d . 1 . .
    C C17 0.77662(18) 0.65520(9) 0.5932(2) 0.0218(4) Uani d . 1 . .
    C C18 0.77655(19) 0.67159(9) 0.8345(2) 0.0227(4) Uani d . 1 . .
    C C19 0.9131(2) 0.40406(10) 0.4010(3) 0.0352(5) Uani d . 1 . .
    H H19A 0.9469 0.3783 0.4815 0.053 Uiso calc R 1 . .
    H H19B 0.9829 0.4211 0.3480 0.053 Uiso calc R 1 . .
    H H19C 0.8590 0.3802 0.3326 0.053 Uiso calc R 1 . .
    C C20 0.4740(2) 0.29656(11) 0.7742(3) 0.0427(6) Uani d . 1 . .
    H H20A 0.4925 0.3177 0.8678 0.064 Uiso calc R 1 . .
    H H20B 0.4726 0.2531 0.7921 0.064 Uiso calc R 1 . .
    H H20C 0.3917 0.3095 0.7316 0.064 Uiso calc R 1 . .
    C C21 0.0789(2) 0.72365(12) 1.1677(3) 0.0387(6) Uani d . 1 . .
    H H21A 0.0098 0.6959 1.1407 0.058 Uiso calc R 1 . .
    H H21B 0.0443 0.7631 1.1909 0.058 Uiso calc R 1 . .
    H H21C 0.1276 0.7081 1.2543 0.058 Uiso calc R 1 . .
    O O1S 0.80228(17) 0.61397(7) 0.19308(17) 0.0374(4) Uani d . 1 . .
    H H1S 0.7956 0.6277 0.2787 0.056 Uiso calc R 1 . .
    C C1S 0.8883(2) 0.56477(11) 0.1984(3) 0.0355(5) Uani d . 1 . .
    H H1S1 0.9573 0.5731 0.2717 0.053 Uiso calc R 1 . .
    H H1S2 0.9226 0.5593 0.1009 0.053 Uiso calc R 1 . .
    H H1S3 0.8442 0.5281 0.2262 0.053 Uiso calc R 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    S1 0.0407(3) 0.0184(3) 0.0178(3) -0.0068(2) -0.0021(2) 0.00092(18)
    O1 0.0325(8) 0.0229(7) 0.0330(8) 0.0030(6) 0.0050(6) -0.0030(6)
    N1 0.0327(9) 0.0184(8) 0.0185(8) -0.0006(7) -0.0005(7) 0.0005(6)
    C1 0.0286(10) 0.0183(10) 0.0215(10) 0.0002(8) -0.0055(8) -0.0022(8)
    O2 0.0421(9) 0.0152(7) 0.0638(12) -0.0006(6) 0.0108(8) 0.0004(7)
    N2 0.0457(11) 0.0208(9) 0.0196(9) -0.0054(8) -0.0004(8) -0.0007(7)
    C2 0.0267(10) 0.0236(10) 0.0232(10) 0.0020(8) -0.0036(8) -0.0015(8)
    O3 0.0432(9) 0.0266(8) 0.0448(10) 0.0034(7) 0.0121(7) -0.0054(7)
    C3 0.0316(11) 0.0203(10) 0.0337(12) 0.0045(8) -0.0033(9) -0.0026(9)
    O4 0.0431(9) 0.0214(7) 0.0185(7) -0.0005(6) 0.0018(6) 0.0010(5)
    C4 0.0326(11) 0.0160(10) 0.0363(12) -0.0020(8) -0.0043(9) 0.0008(8)
    C5 0.0273(10) 0.0201(10) 0.0284(11) -0.0008(8) -0.0032(8) -0.0001(8)
    C6 0.0276(10) 0.0184(9) 0.0211(10) 0.0008(8) -0.0071(8) -0.0023(8)
    C7 0.0264(10) 0.0162(9) 0.0256(11) -0.0015(8) -0.0059(8) -0.0007(8)
    C8 0.0295(11) 0.0190(10) 0.0263(11) -0.0028(8) -0.0047(8) 0.0000(8)
    C9 0.0279(10) 0.0236(10) 0.0227(10) -0.0024(8) -0.0028(8) -0.0019(8)
    C10 0.0356(11) 0.0236(11) 0.0244(11) -0.0031(9) -0.0015(9) 0.0018(8)
    C11 0.0312(11) 0.0348(12) 0.0230(11) -0.0035(9) 0.0022(8) -0.0023(9)
    C12 0.0322(11) 0.0238(11) 0.0325(12) 0.0008(9) -0.0002(9) -0.0076(9)
    C13 0.0440(13) 0.0215(11) 0.0446(14) -0.0035(10) 0.0121(11) -0.0015(10)
    C14 0.0364(12) 0.0229(11) 0.0390(13) -0.0042(9) 0.0098(10) -0.0040(9)
    C15 0.0259(10) 0.0215(10) 0.0192(10) 0.0014(8) -0.0020(8) 0.0012(8)
    C16 0.0249(10) 0.0188(10) 0.0232(10) -0.0005(8) -0.0015(8) 0.0023(8)
    C17 0.0252(10) 0.0195(10) 0.0206(10) 0.0012(8) -0.0010(8) 0.0011(8)
    C18 0.0258(10) 0.0186(9) 0.0234(10) -0.0023(8) -0.0001(8) -0.0017(8)
    C19 0.0337(12) 0.0319(12) 0.0401(13) 0.0067(10) 0.0038(10) -0.0053(10)
    C20 0.0417(14) 0.0210(11) 0.0662(18) -0.0025(10) 0.0092(12) 0.0090(11)
    C21 0.0366(13) 0.0387(13) 0.0413(14) 0.0073(10) 0.0058(10) -0.0064(11)
    O1S 0.0644(11) 0.0277(8) 0.0199(8) 0.0013(8) 0.0020(7) 0.0003(6)
    C1S 0.0409(13) 0.0380(13) 0.0275(12) -0.0060(10) 0.0017(10) -0.0014(10)
_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
    S1 C16 . 1.753(2) ?
    S1 C18 . 1.765(2) ?
    O1 C2 . 1.365(3) ?
    O1 C19 . 1.431(3) ?
    N1 C18 . 1.324(3) ?
    N1 C17 . 1.358(3) ?
    C1 C6 . 1.403(3) ?
    C1 C2 . 1.418(3) ?
    C1 C15 . 1.468(3) ?
    O2 C4 . 1.362(3) ?
    O2 C20 . 1.433(3) ?
    N2 C18 . 1.310(3) ?
    N2 H2A . 0.8800 ?
    N2 H2B . 0.8800 ?
    C2 C3 . 1.375(3) ?
    O3 C12 . 1.375(3) ?
    O3 C21 . 1.426(3) ?
    C3 C4 . 1.401(3) ?
    C3 H3 . 0.9500 ?
    O4 C17 . 1.237(2) ?
    C4 C5 . 1.380(3) ?
    C5 C6 . 1.406(3) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.469(3) ?
    C7 C8 . 1.334(3) ?
    C7 H7 . 0.9500 ?
    C8 C9 . 1.470(3) ?
    C8 H8 . 0.9500 ?
    C9 C10 . 1.390(3) ?
    C9 C14 . 1.399(3) ?
    C10 C11 . 1.394(3) ?
    C10 H10 . 0.9500 ?
    C11 C12 . 1.380(3) ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.388(3) ?
    C13 C14 . 1.378(3) ?
    C13 H13 . 0.9500 ?
    C14 H14 . 0.9500 ?
    C15 C16 . 1.341(3) ?
    C15 H15 . 0.9500 ?
    C16 C17 . 1.501(3) ?
    C19 H19A . 0.9800 ?
    C19 H19B . 0.9800 ?
    C19 H19C . 0.9800 ?
    C20 H20A . 0.9800 ?
    C20 H20B . 0.9800 ?
    C20 H20C . 0.9800 ?
    C21 H21A . 0.9800 ?
    C21 H21B . 0.9800 ?
    C21 H21C . 0.9800 ?
    O1S C1S . 1.425(3) ?
    O1S H1S . 0.8400 ?
    C1S H1S1 . 0.9800 ?
    C1S H1S2 . 0.9800 ?
    C1S H1S3 . 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
    C16 S1 C18 . . 88.54(9) ?
    C2 O1 C19 . . 118.01(17) ?
    C18 N1 C17 . . 111.41(17) ?
    C6 C1 C2 . . 118.67(18) ?
    C6 C1 C15 . . 123.84(18) ?
    C2 C1 C15 . . 117.36(18) ?
    C4 O2 C20 . . 118.05(18) ?
    C18 N2 H2A . . 120.0 ?
    C18 N2 H2B . . 120.0 ?
    H2A N2 H2B . . 120.0 ?
    O1 C2 C3 . . 124.34(19) ?
    O1 C2 C1 . . 114.37(18) ?
    C3 C2 C1 . . 121.28(19) ?
    C12 O3 C21 . . 117.11(18) ?
    C2 C3 C4 . . 118.93(19) ?
    C2 C3 H3 . . 120.5 ?
    C4 C3 H3 . . 120.5 ?
    O2 C4 C5 . . 123.9(2) ?
    O2 C4 C3 . . 114.60(19) ?
    C5 C4 C3 . . 121.50(19) ?
    C4 C5 C6 . . 119.6(2) ?
    C4 C5 H5 . . 120.2 ?
    C6 C5 H5 . . 120.2 ?
    C1 C6 C5 . . 120.01(18) ?
    C1 C6 C7 . . 119.95(18) ?
    C5 C6 C7 . . 119.97(19) ?
    C8 C7 C6 . . 126.26(19) ?
    C8 C7 H7 . . 116.9 ?
    C6 C7 H7 . . 116.9 ?
    C7 C8 C9 . . 125.10(19) ?
    C7 C8 H8 . . 117.5 ?
    C9 C8 H8 . . 117.5 ?
    C10 C9 C14 . . 116.7(2) ?
    C10 C9 C8 . . 120.47(19) ?
    C14 C9 C8 . . 122.80(19) ?
    C9 C10 C11 . . 122.3(2) ?
    C9 C10 H10 . . 118.9 ?
    C11 C10 H10 . . 118.9 ?
    C12 C11 C10 . . 119.4(2) ?
    C12 C11 H11 . . 120.3 ?
    C10 C11 H11 . . 120.3 ?
    O3 C12 C11 . . 124.8(2) ?
    O3 C12 C13 . . 115.6(2) ?
    C11 C12 C13 . . 119.7(2) ?
    C14 C13 C12 . . 120.2(2) ?
    C14 C13 H13 . . 119.9 ?
    C12 C13 H13 . . 119.9 ?
    C13 C14 C9 . . 121.8(2) ?
    C13 C14 H14 . . 119.1 ?
    C9 C14 H14 . . 119.1 ?
    C16 C15 C1 . . 128.05(19) ?
    C16 C15 H15 . . 116.0 ?
    C1 C15 H15 . . 116.0 ?
    C15 C16 C17 . . 124.40(18) ?
    C15 C16 S1 . . 126.89(16) ?
    C17 C16 S1 . . 108.69(14) ?
    O4 C17 N1 . . 122.94(18) ?
    O4 C17 C16 . . 123.11(18) ?
    N1 C17 C16 . . 113.95(17) ?
    N2 C18 N1 . . 123.57(18) ?
    N2 C18 S1 . . 119.09(15) ?
    N1 C18 S1 . . 117.32(15) ?
    O1 C19 H19A . . 109.5 ?
    O1 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    O1 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 109.5 ?
    O2 C20 H20A . . 109.5 ?
    O2 C20 H20B . . 109.5 ?
    H20A C20 H20B . . 109.5 ?
    O2 C20 H20C . . 109.5 ?
    H20A C20 H20C . . 109.5 ?
    H20B C20 H20C . . 109.5 ?
    O3 C21 H21A . . 109.5 ?
    O3 C21 H21B . . 109.5 ?
    H21A C21 H21B . . 109.5 ?
    O3 C21 H21C . . 109.5 ?
    H21A C21 H21C . . 109.5 ?
    H21B C21 H21C . . 109.5 ?
    C1S O1S H1S . . 109.5 ?
    O1S C1S H1S1 . . 109.5 ?
    O1S C1S H1S2 . . 109.5 ?
    H1S1 C1S H1S2 . . 109.5 ?
    O1S C1S H1S3 . . 109.5 ?
    H1S1 C1S H1S3 . . 109.5 ?
    H1S2 C1S H1S3 . . 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
    C19 O1 C2 C3 . . . . 1.1(3) ?
    C19 O1 C2 C1 . . . . 179.79(18) ?
    C6 C1 C2 O1 . . . . 179.80(17) ?
    C15 C1 C2 O1 . . . . 3.9(3) ?
    C6 C1 C2 C3 . . . . -1.5(3) ?
    C15 C1 C2 C3 . . . . -177.44(19) ?
    O1 C2 C3 C4 . . . . 178.09(19) ?
    C1 C2 C3 C4 . . . . -0.5(3) ?
    C20 O2 C4 C5 . . . . -8.1(3) ?
    C20 O2 C4 C3 . . . . 172.3(2) ?
    C2 C3 C4 O2 . . . . -178.10(19) ?
    C2 C3 C4 C5 . . . . 2.3(3) ?
    O2 C4 C5 C6 . . . . 178.4(2) ?
    C3 C4 C5 C6 . . . . -2.0(3) ?
    C2 C1 C6 C5 . . . . 1.8(3) ?
    C15 C1 C6 C5 . . . . 177.43(19) ?
    C2 C1 C6 C7 . . . . -175.00(18) ?
    C15 C1 C6 C7 . . . . 0.7(3) ?
    C4 C5 C6 C1 . . . . -0.1(3) ?
    C4 C5 C6 C7 . . . . 176.70(19) ?
    C1 C6 C7 C8 . . . . -157.3(2) ?
    C5 C6 C7 C8 . . . . 25.9(3) ?
    C6 C7 C8 C9 . . . . 176.15(18) ?
    C7 C8 C9 C10 . . . . 174.4(2) ?
    C7 C8 C9 C14 . . . . -8.0(3) ?
    C14 C9 C10 C11 . . . . 0.1(3) ?
    C8 C9 C10 C11 . . . . 177.91(19) ?
    C9 C10 C11 C12 . . . . -0.2(3) ?
    C21 O3 C12 C11 . . . . 4.0(3) ?
    C21 O3 C12 C13 . . . . -175.4(2) ?
    C10 C11 C12 O3 . . . . -178.8(2) ?
    C10 C11 C12 C13 . . . . 0.6(3) ?
    O3 C12 C13 C14 . . . . 178.5(2) ?
    C11 C12 C13 C14 . . . . -1.0(4) ?
    C12 C13 C14 C9 . . . . 1.0(4) ?
    C10 C9 C14 C13 . . . . -0.5(3) ?
    C8 C9 C14 C13 . . . . -178.2(2) ?
    C6 C1 C15 C16 . . . . 52.1(3) ?
    C2 C1 C15 C16 . . . . -132.2(2) ?
    C1 C15 C16 C17 . . . . -176.34(19) ?
    C1 C15 C16 S1 . . . . 5.2(3) ?
    C18 S1 C16 C15 . . . . 179.4(2) ?
    C18 S1 C16 C17 . . . . 0.77(14) ?
    C18 N1 C17 O4 . . . . -176.10(19) ?
    C18 N1 C17 C16 . . . . 3.4(2) ?
    C15 C16 C17 O4 . . . . -1.8(3) ?
    S1 C16 C17 O4 . . . . 176.94(16) ?
    C15 C16 C17 N1 . . . . 178.79(19) ?
    S1 C16 C17 N1 . . . . -2.5(2) ?
    C17 N1 C18 N2 . . . . 179.14(19) ?
    C17 N1 C18 S1 . . . . -2.8(2) ?
    C16 S1 C18 N2 . . . . 179.25(18) ?
    C16 S1 C18 N1 . . . . 1.12(17) ?
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
    N2 H2A O4 4_576 0.88 2.07 2.926(2) 163
    N2 H2A N1 4_576 0.88 2.64 3.175(2) 120
    N2 H2B O1S 1_556 0.88 2.05 2.872(2) 154
    O1S H1S O4 . 0.84 1.88 2.716(2) 172