##############################################################################
###                                                                        ###
###        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  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2009-02-18
_journal_date_accepted     2009-02-19
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      3
_journal_page_first     o605
_journal_page_last     o605
_journal_paper_category     QO
_journal_coeditor_code     SJ2580
_publ_contact_author
;
     Dr. Seik Weng Ng
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
_publ_contact_author_email     seikweng@um.edu.my
_publ_contact_author_fax     '03 7967 4193'
_publ_contact_author_phone     '03 7967 6778'
_publ_section_title
;
4-(4-Methoxyphenyl)-4-methyl-2,6-diphenyl-4H-thiopyran
;
loop_
    _publ_author_name
    _publ_author_address
    'Rahmani, Hossein'
;
Institute of Chemical Industries
Iranian Research Organization for Science and Technology
PO Box 15815-358
Tehran
Iran
;
    'Pirelahi, Hooshang'
;
Department of Chemistry
College of Science
University of Tehran
PO Box 13145-143
Tehran
Iran
;
    'Ng, Seik Weng'
;
Department of Chemistry
University of Malaya
50603 Kuala Lumpur
 Malaysia
;
_publ_section_synopsis     .
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
4-(4-Methoxyphenyl)-4-methyl-2,6-diphenyl-4H-thiopyran
;
_chemical_name_common     ?
_chemical_formula_moiety     'C25 H22 O S'
_chemical_formula_sum     'C25 H22 O S'
_chemical_formula_iupac     'C25 H22 O S'
_chemical_formula_weight     370.49
_chemical_melting_point     ?
_symmetry_cell_setting     Orthorhombic
_symmetry_space_group_name_H-M     'P c a 21'
_symmetry_space_group_name_Hall     'P 2c -2ac'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, z+1/2'
    'x+1/2, -y, z'
    '-x+1/2, y, z+1/2'
_cell_length_a     14.1567(2)
_cell_length_b     7.61380(10)
_cell_length_c     36.1457(6)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     3896.00(10)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     6600
_cell_measurement_theta_min     2.7
_cell_measurement_theta_max     25.9
_cell_measurement_temperature     115(2)
_exptl_crystal_description     Prism
_exptl_crystal_colour     'Pale yellow'
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.263
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1568
_exptl_absorpt_coefficient_mu     0.178
_exptl_absorpt_correction_type     Multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.919
_exptl_absorpt_correction_T_max     0.982
_diffrn_ambient_temperature     115(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     'Bruker SMART APEX'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     35118
_diffrn_reflns_av_R_equivalents     0.0482
_diffrn_reflns_av_sigmaI/netI     0.0438
_diffrn_reflns_theta_min     1.13
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     27.50
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -18
_diffrn_reflns_limit_h_max     18
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -46
_diffrn_reflns_limit_l_max     46
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     8811
_reflns_number_gt     7499
_reflns_threshold_expression     I>2Ĭ)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0515
_refine_ls_R_factor_gt     0.0396
_refine_ls_wR_factor_gt     0.0956
_refine_ls_wR_factor_ref     0.1062
_refine_ls_goodness_of_fit_ref     1.037
_refine_ls_restrained_S_all     1.037
_refine_ls_number_reflns     8811
_refine_ls_number_parameters     492
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0584P)²+0.3658P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.001
_refine_diff_density_max     0.270
_refine_diff_density_min     -0.255
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983), 4271 Friedel pairs'
_refine_ls_abs_structure_Flack     0.39(6)
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'
    '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     'APEX2 (Bruker, 2008)'
_computing_cell_refinement     'SAINT (Bruker, 2008)'
_computing_data_reduction     'SAINT (Bruker, 2008)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'X-SEED (Barbour, 2001)'
_computing_publication_material     'publCIF (Westrip, 2009)'
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 0.74555(4) 0.75526(7) 0.500000(18) 0.02190(12) Uani d . 1 . .
    S S2 0.48342(4) 0.25554(7) 0.150501(17) 0.02188(12) Uani d . 1 . .
    O O1 0.93417(12) 0.9368(3) 0.30170(5) 0.0335(4) Uani d . 1 . .
    O O2 0.68606(14) 0.6061(3) 0.34833(5) 0.0456(5) Uani d . 1 . .
    C C1 0.66819(14) 0.8115(3) 0.46382(6) 0.0190(5) Uani d . 1 . .
    C C2 0.67887(15) 0.9498(3) 0.44191(7) 0.0213(5) Uani d . 1 . .
    H H2 0.6296 0.9691 0.4245 0.026 Uiso calc R 1 . .
    C C3 0.75898(15) 1.0807(3) 0.44093(6) 0.0198(5) Uani d . 1 . .
    C C4 0.82518(15) 1.0587(3) 0.47343(6) 0.0206(5) Uani d . 1 . .
    H H4 0.8723 1.1465 0.4761 0.025 Uiso calc R 1 . .
    C C5 0.82586(14) 0.9317(3) 0.49885(6) 0.0188(4) Uani d . 1 . .
    C C6 0.71782(18) 1.2682(3) 0.44237(7) 0.0274(5) Uani d . 1 . .
    H H6A 0.6749 1.2856 0.4214 0.041 Uiso calc R 1 . .
    H H6B 0.7693 1.3539 0.4410 0.041 Uiso calc R 1 . .
    H H6C 0.6831 1.2841 0.4656 0.041 Uiso calc R 1 . .
    C C7 0.58948(14) 0.6828(3) 0.45931(6) 0.0196(5) Uani d . 1 . .
    C C8 0.54589(16) 0.6034(3) 0.48994(7) 0.0234(5) Uani d . 1 . .
    H H8 0.5661 0.6320 0.5143 0.028 Uiso calc R 1 . .
    C C9 0.47374(17) 0.4837(3) 0.48484(8) 0.0271(6) Uani d . 1 . .
    H H9 0.4449 0.4303 0.5057 0.033 Uiso calc R 1 . .
    C C10 0.44330(17) 0.4411(3) 0.44995(8) 0.0304(6) Uani d . 1 . .
    H H10 0.3931 0.3597 0.4467 0.036 Uiso calc R 1 . .
    C C11 0.48646(17) 0.5181(4) 0.41938(8) 0.0305(6) Uani d . 1 . .
    H H11 0.4661 0.4880 0.3952 0.037 Uiso calc R 1 . .
    C C12 0.55884(16) 0.6381(3) 0.42407(7) 0.0252(5) Uani d . 1 . .
    H H12 0.5878 0.6902 0.4030 0.030 Uiso calc R 1 . .
    C C13 0.81171(15) 1.0511(3) 0.40405(6) 0.0190(5) Uani d . 1 . .
    C C14 0.76714(17) 1.0842(3) 0.37024(7) 0.0279(5) Uani d . 1 . .
    H H14 0.7055 1.1336 0.3703 0.033 Uiso calc R 1 . .
    C C15 0.80995(17) 1.0473(3) 0.33695(7) 0.0298(5) Uani d . 1 . .
    H H15 0.7780 1.0718 0.3144 0.036 Uiso calc R 1 . .
    C C16 0.89975(17) 0.9743(3) 0.33624(7) 0.0252(5) Uani d . 1 . .
    C C17 0.94639(16) 0.9416(3) 0.36914(7) 0.0248(5) Uani d . 1 . .
    H H17 1.0082 0.8928 0.3690 0.030 Uiso calc R 1 . .
    C C18 0.90181(16) 0.9809(3) 0.40252(7) 0.0226(5) Uani d . 1 . .
    H H18 0.9344 0.9587 0.4250 0.027 Uiso calc R 1 . .
    C C19 1.0242(2) 0.8520(4) 0.29948(8) 0.0426(7) Uani d . 1 . .
    H H19A 1.0396 0.8288 0.2735 0.064 Uiso calc R 1 . .
    H H19B 1.0220 0.7408 0.3131 0.064 Uiso calc R 1 . .
    H H19C 1.0726 0.9282 0.3103 0.064 Uiso calc R 1 . .
    C C20 0.89736(15) 0.9209(3) 0.52889(6) 0.0195(5) Uani d . 1 . .
    C C21 0.99097(17) 0.9677(3) 0.52196(7) 0.0244(5) Uani d . 1 . .
    H H21 1.0085 1.0078 0.4980 0.029 Uiso calc R 1 . .
    C C22 1.05849(18) 0.9563(3) 0.54949(8) 0.0314(6) Uani d . 1 . .
    H H22 1.1219 0.9892 0.5444 0.038 Uiso calc R 1 . .
    C C23 1.03454(18) 0.8975(3) 0.58441(7) 0.0283(5) Uani d . 1 . .
    H H23 1.0810 0.8907 0.6033 0.034 Uiso calc R 1 . .
    C C24 0.94234(18) 0.8488(3) 0.59161(7) 0.0284(5) Uani d . 1 . .
    H H24 0.9256 0.8073 0.6155 0.034 Uiso calc R 1 . .
    C C25 0.87397(16) 0.8599(3) 0.56422(6) 0.0242(5) Uani d . 1 . .
    H H25 0.8108 0.8259 0.5695 0.029 Uiso calc R 1 . .
    C C26 0.40910(15) 0.3075(3) 0.18818(6) 0.0188(5) Uani d . 1 . .
    C C27 0.42127(16) 0.4450(3) 0.21015(7) 0.0219(5) Uani d . 1 . .
    H H27 0.3762 0.4574 0.2294 0.026 Uiso calc R 1 . .
    C C28 0.49713(16) 0.5847(3) 0.20873(6) 0.0205(5) Uani d . 1 . .
    C C29 0.56616(16) 0.5548(3) 0.17759(6) 0.0205(5) Uani d . 1 . .
    H H29 0.6165 0.6368 0.1760 0.025 Uiso calc R 1 . .
    C C30 0.56606(14) 0.4290(3) 0.15210(6) 0.0182(4) Uani d . 1 . .
    C C31 0.44897(18) 0.7633(3) 0.20161(7) 0.0284(5) Uani d . 1 . .
    H H31A 0.4011 0.7845 0.2207 0.043 Uiso calc R 1 . .
    H H31B 0.4188 0.7619 0.1772 0.043 Uiso calc R 1 . .
    H H31C 0.4964 0.8570 0.2024 0.043 Uiso calc R 1 . .
    C C32 0.33001(15) 0.1805(3) 0.19254(6) 0.0207(5) Uani d . 1 . .
    C C33 0.28735(16) 0.1024(3) 0.16188(7) 0.0232(5) Uani d . 1 . .
    H H33 0.3098 0.1288 0.1377 0.028 Uiso calc R 1 . .
    C C34 0.21227(17) -0.0137(3) 0.16624(7) 0.0266(6) Uani d . 1 . .
    H H34 0.1841 -0.0667 0.1452 0.032 Uiso calc R 1 . .
    C C35 0.17863(17) -0.0519(3) 0.20120(8) 0.0299(6) Uani d . 1 . .
    H H35 0.1272 -0.1306 0.2042 0.036 Uiso calc R 1 . .
    C C36 0.22024(18) 0.0251(4) 0.23171(8) 0.0312(6) Uani d . 1 . .
    H H36 0.1968 -0.0001 0.2558 0.037 Uiso calc R 1 . .
    C C37 0.29591(17) 0.1387(3) 0.22755(7) 0.0266(5) Uani d . 1 . .
    H H37 0.3248 0.1886 0.2488 0.032 Uiso calc R 1 . .
    C C38 0.54983(16) 0.5857(3) 0.24607(6) 0.0200(5) Uani d . 1 . .
    C C39 0.50873(17) 0.6610(4) 0.27743(7) 0.0308(6) Uani d . 1 . .
    H H39 0.4476 0.7118 0.2757 0.037 Uiso calc R 1 . .
    C C40 0.55541(19) 0.6629(4) 0.31089(7) 0.0364(6) Uani d . 1 . .
    H H40 0.5258 0.7140 0.3319 0.044 Uiso calc R 1 . .
    C C41 0.64487(17) 0.5912(3) 0.31433(7) 0.0292(5) Uani d . 1 . .
    C C42 0.68627(16) 0.5117(3) 0.28390(7) 0.0252(5) Uani d . 1 . .
    H H42 0.7467 0.4585 0.2860 0.030 Uiso calc R 1 . .
    C C43 0.63812(16) 0.5107(3) 0.25018(7) 0.0220(5) Uani d . 1 . .
    H H43 0.6670 0.4567 0.2294 0.026 Uiso calc R 1 . .
    C C44 0.78270(19) 0.5650(4) 0.35186(7) 0.0374(6) Uani d . 1 . .
    H H44A 0.8047 0.5987 0.3766 0.056 Uiso calc R 1 . .
    H H44B 0.8188 0.6294 0.3331 0.056 Uiso calc R 1 . .
    H H44C 0.7918 0.4385 0.3484 0.056 Uiso calc R 1 . .
    C C45 0.63793(16) 0.4168(3) 0.12220(6) 0.0202(5) Uani d . 1 . .
    C C46 0.73151(17) 0.4634(3) 0.12934(7) 0.0244(5) Uani d . 1 . .
    H H46 0.7490 0.5021 0.1534 0.029 Uiso calc R 1 . .
    C C47 0.79934(18) 0.4539(4) 0.10169(7) 0.0304(6) Uani d . 1 . .
    H H47 0.8627 0.4869 0.1069 0.036 Uiso calc R 1 . .
    C C48 0.77508(18) 0.3966(3) 0.06668(7) 0.0297(6) Uani d . 1 . .
    H H48 0.8215 0.3907 0.0477 0.036 Uiso calc R 1 . .
    C C49 0.68272(18) 0.3478(3) 0.05938(7) 0.0285(5) Uani d . 1 . .
    H H49 0.6658 0.3077 0.0354 0.034 Uiso calc R 1 . .
    C C50 0.61485(17) 0.3571(3) 0.08691(6) 0.0241(5) Uani d . 1 . .
    H H50 0.5518 0.3224 0.0817 0.029 Uiso calc R 1 . .
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 C1 . 1.759(2) ?
    S1 C5 . 1.761(2) ?
    S2 C30 . 1.766(2) ?
    S2 C26 . 1.766(2) ?
    O1 C16 . 1.370(3) ?
    O1 C19 . 1.431(3) ?
    O2 C41 . 1.365(3) ?
    O2 C44 . 1.409(3) ?
    C1 C2 . 1.326(3) ?
    C1 C7 . 1.493(3) ?
    C2 C3 . 1.510(3) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.512(3) ?
    C3 C6 . 1.542(3) ?
    C3 C13 . 1.544(3) ?
    C4 C5 . 1.334(3) ?
    C4 H4 . 0.9500 ?
    C5 C20 . 1.487(3) ?
    C6 H6A . 0.9800 ?
    C6 H6B . 0.9800 ?
    C6 H6C . 0.9800 ?
    C7 C12 . 1.388(3) ?
    C7 C8 . 1.405(3) ?
    C8 C9 . 1.381(3) ?
    C8 H8 . 0.9500 ?
    C9 C10 . 1.372(4) ?
    C9 H9 . 0.9500 ?
    C10 C11 . 1.392(4) ?
    C10 H10 . 0.9500 ?
    C11 C12 . 1.383(3) ?
    C11 H11 . 0.9500 ?
    C12 H12 . 0.9500 ?
    C13 C18 . 1.384(3) ?
    C13 C14 . 1.398(3) ?
    C14 C15 . 1.376(3) ?
    C14 H14 . 0.9500 ?
    C15 C16 . 1.388(3) ?
    C15 H15 . 0.9500 ?
    C16 C17 . 1.383(3) ?
    C17 C18 . 1.394(3) ?
    C17 H17 . 0.9500 ?
    C18 H18 . 0.9500 ?
    C19 H19A . 0.9800 ?
    C19 H19B . 0.9800 ?
    C19 H19C . 0.9800 ?
    C20 C21 . 1.395(3) ?
    C20 C25 . 1.398(3) ?
    C21 C22 . 1.383(4) ?
    C21 H21 . 0.9500 ?
    C22 C23 . 1.381(4) ?
    C22 H22 . 0.9500 ?
    C23 C24 . 1.382(4) ?
    C23 H23 . 0.9500 ?
    C24 C25 . 1.387(3) ?
    C24 H24 . 0.9500 ?
    C25 H25 . 0.9500 ?
    C26 C27 . 1.325(3) ?
    C26 C32 . 1.488(3) ?
    C27 C28 . 1.513(3) ?
    C27 H27 . 0.9500 ?
    C28 C29 . 1.508(3) ?
    C28 C38 . 1.542(3) ?
    C28 C31 . 1.543(3) ?
    C29 C30 . 1.328(3) ?
    C29 H29 . 0.9500 ?
    C30 C45 . 1.487(3) ?
    C31 H31A . 0.9800 ?
    C31 H31B . 0.9800 ?
    C31 H31C . 0.9800 ?
    C32 C37 . 1.391(3) ?
    C32 C33 . 1.395(3) ?
    C33 C34 . 1.391(3) ?
    C33 H33 . 0.9500 ?
    C34 C35 . 1.381(4) ?
    C34 H34 . 0.9500 ?
    C35 C36 . 1.381(4) ?
    C35 H35 . 0.9500 ?
    C36 C37 . 1.385(3) ?
    C36 H36 . 0.9500 ?
    C37 H37 . 0.9500 ?
    C38 C43 . 1.382(3) ?
    C38 C39 . 1.397(3) ?
    C39 C40 . 1.378(4) ?
    C39 H39 . 0.9500 ?
    C40 C41 . 1.385(4) ?
    C40 H40 . 0.9500 ?
    C41 C42 . 1.385(3) ?
    C42 C43 . 1.397(3) ?
    C42 H42 . 0.9500 ?
    C43 H43 . 0.9500 ?
    C44 H44A . 0.9800 ?
    C44 H44B . 0.9800 ?
    C44 H44C . 0.9800 ?
    C45 C50 . 1.393(3) ?
    C45 C46 . 1.396(3) ?
    C46 C47 . 1.388(4) ?
    C46 H46 . 0.9500 ?
    C47 C48 . 1.382(4) ?
    C47 H47 . 0.9500 ?
    C48 C49 . 1.385(3) ?
    C48 H48 . 0.9500 ?
    C49 C50 . 1.385(3) ?
    C49 H49 . 0.9500 ?
    C50 H50 . 0.9500 ?
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
    C1 S1 C5 . . 101.46(11) ?
    C30 S2 C26 . . 101.64(11) ?
    C16 O1 C19 . . 117.5(2) ?
    C41 O2 C44 . . 118.5(2) ?
    C2 C1 C7 . . 122.7(2) ?
    C2 C1 S1 . . 124.50(18) ?
    C7 C1 S1 . . 112.72(16) ?
    C1 C2 C3 . . 128.6(2) ?
    C1 C2 H2 . . 115.7 ?
    C3 C2 H2 . . 115.7 ?
    C2 C3 C4 . . 111.95(19) ?
    C2 C3 C6 . . 109.04(19) ?
    C4 C3 C6 . . 108.10(19) ?
    C2 C3 C13 . . 106.66(18) ?
    C4 C3 C13 . . 110.78(18) ?
    C6 C3 C13 . . 110.31(19) ?
    C5 C4 C3 . . 128.3(2) ?
    C5 C4 H4 . . 115.8 ?
    C3 C4 H4 . . 115.8 ?
    C4 C5 C20 . . 123.3(2) ?
    C4 C5 S1 . . 124.38(18) ?
    C20 C5 S1 . . 112.33(16) ?
    C3 C6 H6A . . 109.5 ?
    C3 C6 H6B . . 109.5 ?
    H6A C6 H6B . . 109.5 ?
    C3 C6 H6C . . 109.5 ?
    H6A C6 H6C . . 109.5 ?
    H6B C6 H6C . . 109.5 ?
    C12 C7 C8 . . 118.7(2) ?
    C12 C7 C1 . . 119.7(2) ?
    C8 C7 C1 . . 121.6(2) ?
    C9 C8 C7 . . 120.3(2) ?
    C9 C8 H8 . . 119.9 ?
    C7 C8 H8 . . 119.9 ?
    C10 C9 C8 . . 120.7(2) ?
    C10 C9 H9 . . 119.6 ?
    C8 C9 H9 . . 119.6 ?
    C9 C10 C11 . . 119.5(2) ?
    C9 C10 H10 . . 120.2 ?
    C11 C10 H10 . . 120.2 ?
    C12 C11 C10 . . 120.4(3) ?
    C12 C11 H11 . . 119.8 ?
    C10 C11 H11 . . 119.8 ?
    C11 C12 C7 . . 120.4(2) ?
    C11 C12 H12 . . 119.8 ?
    C7 C12 H12 . . 119.8 ?
    C18 C13 C14 . . 116.8(2) ?
    C18 C13 C3 . . 122.4(2) ?
    C14 C13 C3 . . 120.7(2) ?
    C15 C14 C13 . . 121.9(2) ?
    C15 C14 H14 . . 119.0 ?
    C13 C14 H14 . . 119.0 ?
    C14 C15 C16 . . 120.1(2) ?
    C14 C15 H15 . . 120.0 ?
    C16 C15 H15 . . 120.0 ?
    O1 C16 C17 . . 125.2(2) ?
    O1 C16 C15 . . 115.2(2) ?
    C17 C16 C15 . . 119.6(2) ?
    C16 C17 C18 . . 119.3(2) ?
    C16 C17 H17 . . 120.3 ?
    C18 C17 H17 . . 120.3 ?
    C13 C18 C17 . . 122.3(2) ?
    C13 C18 H18 . . 118.8 ?
    C17 C18 H18 . . 118.8 ?
    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 ?
    C21 C20 C25 . . 118.3(2) ?
    C21 C20 C5 . . 120.1(2) ?
    C25 C20 C5 . . 121.6(2) ?
    C22 C21 C20 . . 120.8(2) ?
    C22 C21 H21 . . 119.6 ?
    C20 C21 H21 . . 119.6 ?
    C23 C22 C21 . . 120.6(2) ?
    C23 C22 H22 . . 119.7 ?
    C21 C22 H22 . . 119.7 ?
    C22 C23 C24 . . 119.4(2) ?
    C22 C23 H23 . . 120.3 ?
    C24 C23 H23 . . 120.3 ?
    C23 C24 C25 . . 120.5(2) ?
    C23 C24 H24 . . 119.7 ?
    C25 C24 H24 . . 119.7 ?
    C24 C25 C20 . . 120.5(2) ?
    C24 C25 H25 . . 119.8 ?
    C20 C25 H25 . . 119.8 ?
    C27 C26 C32 . . 123.2(2) ?
    C27 C26 S2 . . 124.19(19) ?
    C32 C26 S2 . . 112.61(16) ?
    C26 C27 C28 . . 128.9(2) ?
    C26 C27 H27 . . 115.6 ?
    C28 C27 H27 . . 115.6 ?
    C29 C28 C27 . . 112.27(19) ?
    C29 C28 C38 . . 109.90(18) ?
    C27 C28 C38 . . 108.47(18) ?
    C29 C28 C31 . . 107.18(19) ?
    C27 C28 C31 . . 108.18(19) ?
    C38 C28 C31 . . 110.84(18) ?
    C30 C29 C28 . . 128.8(2) ?
    C30 C29 H29 . . 115.6 ?
    C28 C29 H29 . . 115.6 ?
    C29 C30 C45 . . 123.3(2) ?
    C29 C30 S2 . . 124.23(18) ?
    C45 C30 S2 . . 112.48(16) ?
    C28 C31 H31A . . 109.5 ?
    C28 C31 H31B . . 109.5 ?
    H31A C31 H31B . . 109.5 ?
    C28 C31 H31C . . 109.5 ?
    H31A C31 H31C . . 109.5 ?
    H31B C31 H31C . . 109.5 ?
    C37 C32 C33 . . 118.3(2) ?
    C37 C32 C26 . . 120.4(2) ?
    C33 C32 C26 . . 121.2(2) ?
    C34 C33 C32 . . 120.8(2) ?
    C34 C33 H33 . . 119.6 ?
    C32 C33 H33 . . 119.6 ?
    C35 C34 C33 . . 120.1(2) ?
    C35 C34 H34 . . 120.0 ?
    C33 C34 H34 . . 120.0 ?
    C36 C35 C34 . . 119.6(2) ?
    C36 C35 H35 . . 120.2 ?
    C34 C35 H35 . . 120.2 ?
    C35 C36 C37 . . 120.5(3) ?
    C35 C36 H36 . . 119.7 ?
    C37 C36 H36 . . 119.7 ?
    C36 C37 C32 . . 120.7(2) ?
    C36 C37 H37 . . 119.7 ?
    C32 C37 H37 . . 119.7 ?
    C43 C38 C39 . . 117.3(2) ?
    C43 C38 C28 . . 122.0(2) ?
    C39 C38 C28 . . 120.7(2) ?
    C40 C39 C38 . . 121.1(2) ?
    C40 C39 H39 . . 119.4 ?
    C38 C39 H39 . . 119.4 ?
    C39 C40 C41 . . 120.9(2) ?
    C39 C40 H40 . . 119.6 ?
    C41 C40 H40 . . 119.6 ?
    O2 C41 C40 . . 116.0(2) ?
    O2 C41 C42 . . 124.8(2) ?
    C40 C41 C42 . . 119.2(2) ?
    C41 C42 C43 . . 119.3(2) ?
    C41 C42 H42 . . 120.4 ?
    C43 C42 H42 . . 120.4 ?
    C38 C43 C42 . . 122.2(2) ?
    C38 C43 H43 . . 118.9 ?
    C42 C43 H43 . . 118.9 ?
    O2 C44 H44A . . 109.5 ?
    O2 C44 H44B . . 109.5 ?
    H44A C44 H44B . . 109.5 ?
    O2 C44 H44C . . 109.5 ?
    H44A C44 H44C . . 109.5 ?
    H44B C44 H44C . . 109.5 ?
    C50 C45 C46 . . 118.4(2) ?
    C50 C45 C30 . . 121.7(2) ?
    C46 C45 C30 . . 119.9(2) ?
    C47 C46 C45 . . 120.7(2) ?
    C47 C46 H46 . . 119.7 ?
    C45 C46 H46 . . 119.7 ?
    C48 C47 C46 . . 120.3(2) ?
    C48 C47 H47 . . 119.9 ?
    C46 C47 H47 . . 119.9 ?
    C47 C48 C49 . . 119.6(2) ?
    C47 C48 H48 . . 120.2 ?
    C49 C48 H48 . . 120.2 ?
    C48 C49 C50 . . 120.3(2) ?
    C48 C49 H49 . . 119.9 ?
    C50 C49 H49 . . 119.9 ?
    C49 C50 C45 . . 120.8(2) ?
    C49 C50 H50 . . 119.6 ?
    C45 C50 H50 . . 119.6 ?
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
    C5 S1 C1 C2 . . . . 3.5(2) ?
    C5 S1 C1 C7 . . . . -178.39(15) ?
    C7 C1 C2 C3 . . . . -174.0(2) ?
    S1 C1 C2 C3 . . . . 4.0(4) ?
    C1 C2 C3 C4 . . . . -9.7(3) ?
    C1 C2 C3 C6 . . . . -129.3(3) ?
    C1 C2 C3 C13 . . . . 111.6(3) ?
    C2 C3 C4 C5 . . . . 7.7(3) ?
    C6 C3 C4 C5 . . . . 127.8(3) ?
    C13 C3 C4 C5 . . . . -111.2(3) ?
    C3 C4 C5 C20 . . . . 177.6(2) ?
    C3 C4 C5 S1 . . . . -0.3(3) ?
    C1 S1 C5 C4 . . . . -5.2(2) ?
    C1 S1 C5 C20 . . . . 176.71(15) ?
    C2 C1 C7 C12 . . . . 36.8(3) ?
    S1 C1 C7 C12 . . . . -141.36(19) ?
    C2 C1 C7 C8 . . . . -144.0(2) ?
    S1 C1 C7 C8 . . . . 37.8(3) ?
    C12 C7 C8 C9 . . . . -0.3(3) ?
    C1 C7 C8 C9 . . . . -179.5(2) ?
    C7 C8 C9 C10 . . . . -0.3(4) ?
    C8 C9 C10 C11 . . . . 0.7(4) ?
    C9 C10 C11 C12 . . . . -0.7(4) ?
    C10 C11 C12 C7 . . . . 0.2(4) ?
    C8 C7 C12 C11 . . . . 0.3(4) ?
    C1 C7 C12 C11 . . . . 179.5(2) ?
    C2 C3 C13 C18 . . . . -110.6(2) ?
    C4 C3 C13 C18 . . . . 11.5(3) ?
    C6 C3 C13 C18 . . . . 131.1(2) ?
    C2 C3 C13 C14 . . . . 65.2(3) ?
    C4 C3 C13 C14 . . . . -172.7(2) ?
    C6 C3 C13 C14 . . . . -53.1(3) ?
    C18 C13 C14 C15 . . . . 0.7(4) ?
    C3 C13 C14 C15 . . . . -175.3(2) ?
    C13 C14 C15 C16 . . . . 0.3(4) ?
    C19 O1 C16 C17 . . . . 2.1(4) ?
    C19 O1 C16 C15 . . . . -176.5(2) ?
    C14 C15 C16 O1 . . . . 177.6(2) ?
    C14 C15 C16 C17 . . . . -1.0(4) ?
    O1 C16 C17 C18 . . . . -177.8(2) ?
    C15 C16 C17 C18 . . . . 0.7(3) ?
    C14 C13 C18 C17 . . . . -1.0(3) ?
    C3 C13 C18 C17 . . . . 174.9(2) ?
    C16 C17 C18 C13 . . . . 0.4(4) ?
    C4 C5 C20 C21 . . . . -37.1(3) ?
    S1 C5 C20 C21 . . . . 141.01(19) ?
    C4 C5 C20 C25 . . . . 144.6(2) ?
    S1 C5 C20 C25 . . . . -37.3(3) ?
    C25 C20 C21 C22 . . . . -0.9(4) ?
    C5 C20 C21 C22 . . . . -179.2(2) ?
    C20 C21 C22 C23 . . . . 0.3(4) ?
    C21 C22 C23 C24 . . . . 0.4(4) ?
    C22 C23 C24 C25 . . . . -0.6(4) ?
    C23 C24 C25 C20 . . . . -0.1(4) ?
    C21 C20 C25 C24 . . . . 0.8(3) ?
    C5 C20 C25 C24 . . . . 179.1(2) ?
    C30 S2 C26 C27 . . . . -0.8(2) ?
    C30 S2 C26 C32 . . . . 178.67(15) ?
    C32 C26 C27 C28 . . . . -179.3(2) ?
    S2 C26 C27 C28 . . . . 0.2(4) ?
    C26 C27 C28 C29 . . . . -0.5(3) ?
    C26 C27 C28 C38 . . . . -122.1(3) ?
    C26 C27 C28 C31 . . . . 117.6(3) ?
    C27 C28 C29 C30 . . . . 2.0(3) ?
    C38 C28 C29 C30 . . . . 122.8(2) ?
    C31 C28 C29 C30 . . . . -116.6(3) ?
    C28 C29 C30 C45 . . . . 178.7(2) ?
    C28 C29 C30 S2 . . . . -3.1(3) ?
    C26 S2 C30 C29 . . . . 2.2(2) ?
    C26 S2 C30 C45 . . . . -179.44(15) ?
    C27 C26 C32 C37 . . . . -34.2(3) ?
    S2 C26 C32 C37 . . . . 146.29(19) ?
    C27 C26 C32 C33 . . . . 144.9(2) ?
    S2 C26 C32 C33 . . . . -34.6(3) ?
    C37 C32 C33 C34 . . . . 0.3(3) ?
    C26 C32 C33 C34 . . . . -178.8(2) ?
    C32 C33 C34 C35 . . . . 0.5(4) ?
    C33 C34 C35 C36 . . . . -0.3(4) ?
    C34 C35 C36 C37 . . . . -0.6(4) ?
    C35 C36 C37 C32 . . . . 1.5(4) ?
    C33 C32 C37 C36 . . . . -1.3(4) ?
    C26 C32 C37 C36 . . . . 177.8(2) ?
    C29 C28 C38 C43 . . . . -20.2(3) ?
    C27 C28 C38 C43 . . . . 102.9(2) ?
    C31 C28 C38 C43 . . . . -138.4(2) ?
    C29 C28 C38 C39 . . . . 160.8(2) ?
    C27 C28 C38 C39 . . . . -76.1(3) ?
    C31 C28 C38 C39 . . . . 42.5(3) ?
    C43 C38 C39 C40 . . . . 1.1(4) ?
    C28 C38 C39 C40 . . . . -179.8(2) ?
    C38 C39 C40 C41 . . . . 0.5(4) ?
    C44 O2 C41 C40 . . . . -168.6(2) ?
    C44 O2 C41 C42 . . . . 11.0(4) ?
    C39 C40 C41 O2 . . . . 177.6(3) ?
    C39 C40 C41 C42 . . . . -2.1(4) ?
    O2 C41 C42 C43 . . . . -177.6(2) ?
    C40 C41 C42 C43 . . . . 2.0(4) ?
    C39 C38 C43 C42 . . . . -1.2(3) ?
    C28 C38 C43 C42 . . . . 179.8(2) ?
    C41 C42 C43 C38 . . . . -0.4(4) ?
    C29 C30 C45 C50 . . . . -144.9(2) ?
    S2 C30 C45 C50 . . . . 36.7(3) ?
    C29 C30 C45 C46 . . . . 36.0(3) ?
    S2 C30 C45 C46 . . . . -142.44(19) ?
    C50 C45 C46 C47 . . . . 1.3(4) ?
    C30 C45 C46 C47 . . . . -179.6(2) ?
    C45 C46 C47 C48 . . . . -0.5(4) ?
    C46 C47 C48 C49 . . . . -0.3(4) ?
    C47 C48 C49 C50 . . . . 0.3(4) ?
    C48 C49 C50 C45 . . . . 0.5(4) ?
    C46 C45 C50 C49 . . . . -1.3(3) ?
    C30 C45 C50 C49 . . . . 179.6(2) ?
