##############################################################################
###                                                                        ###
###        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 2.1.    #
#                                                                            #
# 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/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2007-10-06
_journal_date_accepted     2007-10-13
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue     11
_journal_page_first     o4365
_journal_page_last     o4365
_journal_paper_category     QO
_journal_coeditor_code     IS2220
_publ_contact_author_name     'Zeng Xiao-Hua'
_publ_contact_author_address
; Department of Medicinal Chemistry, Yunyang Medical College, Shiyan 442000
  P.R. China
;
_publ_contact_author_email     zken710@yahoo.com.cn
_publ_contact_author_fax     '86 719 8875337'
_publ_contact_author_phone     '86 13593720854'
_publ_section_title
;\
3-Butyl-2-(piperidin-1-yl)-5,6,7,8-tetrahydrobenzothieno[2,3-d]\
pyrimidin-4(3H)-one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Wang, Hong-Mei' .
; Department of Medicinal Chemistry, Yunyang Medical College, Shiyan 442000
People's Republic of China
;
    'Zeng, Xiao-Hua' .
; Department of Medicinal Chemistry, Yunyang Medical College, Shiyan 442000
People's Republic of China
;
    'Zheng, Ai-Hua' .
; Department of Medicinal Chemistry, Yunyang Medical College, Shiyan 442000
People's Republic of China
;
    'Tian, Jia-Hua' .
; Department of Medicinal Chemistry, Yunyang Medical College, Shiyan 442000
People's Republic of China
;
    'He, Ting-Yun' .
; Department of Medicinal Chemistry, Yunyang Medical College, Shiyan 442000
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
3-Butyl-2-(piperidin-1-yl)-5,6,7,8-tetrahydrobenzothieno[2,3-d]pyrimidin-
4(3H)-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H27 N3 O S'
_chemical_formula_sum     'C19 H27 N3 O S'
_chemical_formula_iupac     'C19 H27 N3 O S'
_chemical_formula_weight     345.50
_chemical_melting_point     ?
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     9.8979(8)
_cell_length_b     10.3679(9)
_cell_length_c     10.9645(9)
_cell_angle_alpha     113.5370(10)
_cell_angle_beta     107.6790(10)
_cell_angle_gamma     100.1670(10)
_cell_volume     923.97(13)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1934
_cell_measurement_theta_min     2.23
_cell_measurement_theta_max     22.41
_cell_measurement_temperature     292(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.06
_exptl_crystal_size_min     0.02
_exptl_crystal_density_diffrn     1.242
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     372
_exptl_absorpt_coefficient_mu     0.186
_exptl_absorpt_correction_type     none
_exptl_special_details
;
;
_diffrn_ambient_temperature     292(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 CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     7700
_diffrn_reflns_av_R_equivalents     0.0438
_diffrn_reflns_av_sigmaI/netI     0.0592
_diffrn_reflns_theta_min     2.23
_diffrn_reflns_theta_max     26.00
_diffrn_reflns_theta_full     26.00
_diffrn_measured_fraction_theta_max     0.987
_diffrn_measured_fraction_theta_full     0.987
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3587
_reflns_number_gt     2271
_reflns_threshold_expression     'I>2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0909
_refine_ls_R_factor_gt     0.0588
_refine_ls_wR_factor_gt     0.1499
_refine_ls_wR_factor_ref     0.1838
_refine_ls_goodness_of_fit_ref     1.026
_refine_ls_restrained_S_all     1.026
_refine_ls_number_reflns     3587
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0975P)²] 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     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.309
_refine_diff_density_min     -0.294
_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     'SMART (Bruker, 2001)'
_computing_cell_refinement     'SAINT (Bruker, 2001)'
_computing_data_reduction     'SAINT (Bruker, 2001)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON (Spek, 2003)'
_computing_publication_material     'SHELXTL (Sheldrick, 2001)'
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 0.40177(10) 0.46312(8) 0.21177(8) 0.0609(3) Uani d . 1 . .
    N N1 0.3069(2) 0.1715(2) 0.1435(2) 0.0465(6) Uani d . 1 . .
    N N2 0.1870(2) 0.1033(2) 0.2765(2) 0.0434(5) Uani d . 1 . .
    C C8 0.2699(3) 0.3619(3) 0.3400(3) 0.0439(7) Uani d . 1 . .
    N N3 0.2303(2) -0.0775(2) 0.0898(2) 0.0456(6) Uani d . 1 . .
    O O1 0.1534(3) 0.2739(2) 0.4653(2) 0.0698(7) Uani d . 1 . .
    C C16 0.1233(3) -0.0109(3) 0.3111(3) 0.0484(7) Uani d . 1 . .
    H H16A 0.1728 0.0261 0.4155 0.058 Uiso calc R 1 . .
    H H16B 0.1451 -0.1005 0.2622 0.058 Uiso calc R 1 . .
    C C9 0.1995(3) 0.2514(3) 0.3694(3) 0.0486(7) Uani d . 1 . .
    C C10 0.2415(3) 0.0708(3) 0.1690(3) 0.0417(6) Uani d . 1 . .
    C C1 0.2966(3) 0.5199(3) 0.4082(3) 0.0453(7) Uani d . 1 . .
    C C7 0.3202(3) 0.3150(3) 0.2314(3) 0.0456(7) Uani d . 1 . .
    C C6 0.3667(3) 0.5875(3) 0.3505(3) 0.0494(7) Uani d . 1 . .
    C C11 0.0765(3) -0.1862(3) -0.0144(3) 0.0496(7) Uani d . 1 . .
    H H11A 0.0417 -0.1704 -0.0984 0.060 Uiso calc R 1 . .
    H H11B 0.0077 -0.1703 0.0325 0.060 Uiso calc R 1 . .
    C C17 -0.0465(3) -0.0517(3) 0.2656(3) 0.0520(7) Uani d . 1 . .
    H H17A -0.0666 0.0299 0.3320 0.062 Uiso calc R 1 . .
    H H17B -0.0941 -0.0642 0.1683 0.062 Uiso calc R 1 . .
    C C2 0.2488(4) 0.6038(3) 0.5266(3) 0.0595(8) Uani d . 1 . .
    H H2A 0.3113 0.6105 0.6178 0.071 Uiso calc R 1 . .
    H H2B 0.1449 0.5502 0.5003 0.071 Uiso calc R 1 . .
    C C15 0.3358(3) -0.0959(3) 0.0196(3) 0.0571(8) Uani d . 1 . .
    H H15A 0.4361 -0.0251 0.0891 0.069 Uiso calc R 1 . .
    H H15B 0.3044 -0.0759 -0.0620 0.069 Uiso calc R 1 . .
    C C12 0.0763(4) -0.3444(3) -0.0643(3) 0.0644(9) Uani d . 1 . .
    H H12A -0.0248 -0.4141 -0.1324 0.077 Uiso calc R 1 . .
    H H12B 0.1072 -0.3617 0.0190 0.077 Uiso calc R 1 . .
    C C18 -0.1149(3) -0.1924(4) 0.2660(4) 0.0645(9) Uani d . 1 . .
    H H18A -0.0679 -0.1798 0.3635 0.077 Uiso calc R 1 . .
    H H18B -0.0941 -0.2739 0.2002 0.077 Uiso calc R 1 . .
    C C5 0.4085(4) 0.7505(3) 0.3967(3) 0.0626(8) Uani d . 1 . .
    H H5A 0.5133 0.7899 0.4151 0.075 Uiso calc R 1 . .
    H H5B 0.3472 0.7643 0.3183 0.075 Uiso calc R 1 . .
    C C14 0.3392(4) -0.2539(4) -0.0343(4) 0.0725(10) Uani d . 1 . .
    H H14A 0.3794 -0.2700 0.0488 0.087 Uiso calc R 1 . .
    H H14B 0.4061 -0.2661 -0.0838 0.087 Uiso calc R 1 . .
    C C13 0.1840(4) -0.3699(4) -0.1381(4) 0.0768(10) Uani d . 1 . .
    H H13A 0.1892 -0.4695 -0.1644 0.092 Uiso calc R 1 . .
    H H13B 0.1478 -0.3622 -0.2268 0.092 Uiso calc R 1 . .
    C C3 0.2643(5) 0.7599(4) 0.5461(5) 0.1045(15) Uani d . 1 . .
    H H3A 0.1719 0.7538 0.4765 0.125 Uiso calc R 1 . .
    H H3B 0.2716 0.8223 0.6431 0.125 Uiso calc R 1 . .
    C C4 0.3868(5) 0.8343(4) 0.5298(4) 0.0913(13) Uani d . 1 . .
    H H4A 0.4786 0.8629 0.6139 0.110 Uiso calc R 1 . .
    H H4B 0.3737 0.9257 0.5323 0.110 Uiso calc R 1 . .
    C C19 -0.2845(4) -0.2338(4) 0.2196(4) 0.0811(11) Uani d . 1 . .
    H H19A -0.3059 -0.1533 0.2839 0.122 Uiso calc R 1 . .
    H H19B -0.3224 -0.3228 0.2242 0.122 Uiso calc R 1 . .
    H H19C -0.3323 -0.2514 0.1212 0.122 Uiso calc R 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
    S1 C7 . 1.728(3) ?
    S1 C6 . 1.735(3) ?
    N1 C10 . 1.302(3) ?
    N1 C7 . 1.367(3) ?
    N2 C10 . 1.388(3) ?
    N2 C9 . 1.420(3) ?
    N2 C16 . 1.477(3) ?
    C8 C7 . 1.373(3) ?
    C8 C9 . 1.433(4) ?
    C8 C1 . 1.436(4) ?
    N3 C10 . 1.394(3) ?
    N3 C15 . 1.470(3) ?
    N3 C11 . 1.485(3) ?
    O1 C9 . 1.225(3) ?
    C16 C17 . 1.524(4) ?
    C16 H16A . 0.9700 ?
    C16 H16B . 0.9700 ?
    C1 C6 . 1.350(4) ?
    C1 C2 . 1.510(3) ?
    C6 C5 . 1.492(4) ?
    C11 C12 . 1.506(4) ?
    C11 H11A . 0.9700 ?
    C11 H11B . 0.9700 ?
    C17 C18 . 1.498(4) ?
    C17 H17A . 0.9700 ?
    C17 H17B . 0.9700 ?
    C2 C3 . 1.518(5) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C15 C14 . 1.513(4) ?
    C15 H15A . 0.9700 ?
    C15 H15B . 0.9700 ?
    C12 C13 . 1.521(5) ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
    C18 C19 . 1.521(4) ?
    C18 H18A . 0.9700 ?
    C18 H18B . 0.9700 ?
    C5 C4 . 1.475(4) ?
    C5 H5A . 0.9700 ?
    C5 H5B . 0.9700 ?
    C14 C13 . 1.515(5) ?
    C14 H14A . 0.9700 ?
    C14 H14B . 0.9700 ?
    C13 H13A . 0.9700 ?
    C13 H13B . 0.9700 ?
    C3 C4 . 1.417(5) ?
    C3 H3A . 0.9700 ?
    C3 H3B . 0.9700 ?
    C4 H4A . 0.9700 ?
    C4 H4B . 0.9700 ?
    C19 H19A . 0.9600 ?
    C19 H19B . 0.9600 ?
    C19 H19C . 0.9600 ?
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
    C7 S1 C6 . . 91.25(13) ?
    C10 N1 C7 . . 115.3(2) ?
    C10 N2 C9 . . 122.3(2) ?
    C10 N2 C16 . . 122.7(2) ?
    C9 N2 C16 . . 114.9(2) ?
    C7 C8 C9 . . 117.7(2) ?
    C7 C8 C1 . . 113.0(2) ?
    C9 C8 C1 . . 129.3(2) ?
    C10 N3 C15 . . 114.1(2) ?
    C10 N3 C11 . . 116.6(2) ?
    C15 N3 C11 . . 110.6(2) ?
    N2 C16 C17 . . 113.6(2) ?
    N2 C16 H16A . . 108.8 ?
    C17 C16 H16A . . 108.8 ?
    N2 C16 H16B . . 108.8 ?
    C17 C16 H16B . . 108.8 ?
    H16A C16 H16B . . 107.7 ?
    O1 C9 N2 . . 119.4(3) ?
    O1 C9 C8 . . 126.5(2) ?
    N2 C9 C8 . . 114.1(2) ?
    N1 C10 N2 . . 123.5(2) ?
    N1 C10 N3 . . 119.2(2) ?
    N2 C10 N3 . . 117.2(2) ?
    C6 C1 C8 . . 111.9(2) ?
    C6 C1 C2 . . 122.5(3) ?
    C8 C1 C2 . . 125.6(3) ?
    N1 C7 C8 . . 127.0(3) ?
    N1 C7 S1 . . 121.77(19) ?
    C8 C7 S1 . . 111.2(2) ?
    C1 C6 C5 . . 124.8(3) ?
    C1 C6 S1 . . 112.6(2) ?
    C5 C6 S1 . . 122.5(2) ?
    N3 C11 C12 . . 110.6(2) ?
    N3 C11 H11A . . 109.5 ?
    C12 C11 H11A . . 109.5 ?
    N3 C11 H11B . . 109.5 ?
    C12 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 108.1 ?
    C18 C17 C16 . . 112.7(2) ?
    C18 C17 H17A . . 109.1 ?
    C16 C17 H17A . . 109.1 ?
    C18 C17 H17B . . 109.1 ?
    C16 C17 H17B . . 109.1 ?
    H17A C17 H17B . . 107.8 ?
    C1 C2 C3 . . 110.0(3) ?
    C1 C2 H2A . . 109.7 ?
    C3 C2 H2A . . 109.7 ?
    C1 C2 H2B . . 109.7 ?
    C3 C2 H2B . . 109.7 ?
    H2A C2 H2B . . 108.2 ?
    N3 C15 C14 . . 109.8(3) ?
    N3 C15 H15A . . 109.7 ?
    C14 C15 H15A . . 109.7 ?
    N3 C15 H15B . . 109.7 ?
    C14 C15 H15B . . 109.7 ?
    H15A C15 H15B . . 108.2 ?
    C11 C12 C13 . . 109.7(3) ?
    C11 C12 H12A . . 109.7 ?
    C13 C12 H12A . . 109.7 ?
    C11 C12 H12B . . 109.7 ?
    C13 C12 H12B . . 109.7 ?
    H12A C12 H12B . . 108.2 ?
    C17 C18 C19 . . 112.7(3) ?
    C17 C18 H18A . . 109.1 ?
    C19 C18 H18A . . 109.1 ?
    C17 C18 H18B . . 109.1 ?
    C19 C18 H18B . . 109.1 ?
    H18A C18 H18B . . 107.8 ?
    C4 C5 C6 . . 111.5(3) ?
    C4 C5 H5A . . 109.3 ?
    C6 C5 H5A . . 109.3 ?
    C4 C5 H5B . . 109.3 ?
    C6 C5 H5B . . 109.3 ?
    H5A C5 H5B . . 108.0 ?
    C15 C14 C13 . . 112.1(3) ?
    C15 C14 H14A . . 109.2 ?
    C13 C14 H14A . . 109.2 ?
    C15 C14 H14B . . 109.2 ?
    C13 C14 H14B . . 109.2 ?
    H14A C14 H14B . . 107.9 ?
    C14 C13 C12 . . 109.3(3) ?
    C14 C13 H13A . . 109.8 ?
    C12 C13 H13A . . 109.8 ?
    C14 C13 H13B . . 109.8 ?
    C12 C13 H13B . . 109.8 ?
    H13A C13 H13B . . 108.3 ?
    C4 C3 C2 . . 117.9(3) ?
    C4 C3 H3A . . 107.8 ?
    C2 C3 H3A . . 107.8 ?
    C4 C3 H3B . . 107.8 ?
    C2 C3 H3B . . 107.8 ?
    H3A C3 H3B . . 107.2 ?
    C3 C4 C5 . . 116.9(3) ?
    C3 C4 H4A . . 108.1 ?
    C5 C4 H4A . . 108.1 ?
    C3 C4 H4B . . 108.1 ?
    C5 C4 H4B . . 108.1 ?
    H4A C4 H4B . . 107.3 ?
    C18 C19 H19A . . 109.5 ?
    C18 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    C18 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 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
    C10 N2 C16 C17 . . . . -110.2(3) ?
    C9 N2 C16 C17 . . . . 74.5(3) ?
    C10 N2 C9 O1 . . . . -177.9(2) ?
    C16 N2 C9 O1 . . . . -2.6(4) ?
    C10 N2 C9 C8 . . . . 1.2(4) ?
    C16 N2 C9 C8 . . . . 176.4(2) ?
    C7 C8 C9 O1 . . . . 177.1(3) ?
    C1 C8 C9 O1 . . . . -3.2(5) ?
    C7 C8 C9 N2 . . . . -1.8(4) ?
    C1 C8 C9 N2 . . . . 177.9(2) ?
    C7 N1 C10 N2 . . . . 0.4(4) ?
    C7 N1 C10 N3 . . . . -176.6(2) ?
    C9 N2 C10 N1 . . . . -0.5(4) ?
    C16 N2 C10 N1 . . . . -175.4(2) ?
    C9 N2 C10 N3 . . . . 176.6(2) ?
    C16 N2 C10 N3 . . . . 1.7(4) ?
    C15 N3 C10 N1 . . . . 18.8(3) ?
    C11 N3 C10 N1 . . . . -112.1(3) ?
    C15 N3 C10 N2 . . . . -158.4(2) ?
    C11 N3 C10 N2 . . . . 70.7(3) ?
    C7 C8 C1 C6 . . . . -0.5(3) ?
    C9 C8 C1 C6 . . . . 179.8(3) ?
    C7 C8 C1 C2 . . . . 177.4(2) ?
    C9 C8 C1 C2 . . . . -2.3(5) ?
    C10 N1 C7 C8 . . . . -1.2(4) ?
    C10 N1 C7 S1 . . . . -179.1(2) ?
    C9 C8 C7 N1 . . . . 2.0(4) ?
    C1 C8 C7 N1 . . . . -177.7(2) ?
    C9 C8 C7 S1 . . . . -179.9(2) ?
    C1 C8 C7 S1 . . . . 0.4(3) ?
    C6 S1 C7 N1 . . . . 178.1(2) ?
    C6 S1 C7 C8 . . . . -0.1(2) ?
    C8 C1 C6 C5 . . . . 179.3(3) ?
    C2 C1 C6 C5 . . . . 1.4(4) ?
    C8 C1 C6 S1 . . . . 0.4(3) ?
    C2 C1 C6 S1 . . . . -177.6(2) ?
    C7 S1 C6 C1 . . . . -0.1(2) ?
    C7 S1 C6 C5 . . . . -179.1(3) ?
    C10 N3 C11 C12 . . . . -166.3(2) ?
    C15 N3 C11 C12 . . . . 61.1(3) ?
    N2 C16 C17 C18 . . . . 165.4(2) ?
    C6 C1 C2 C3 . . . . 10.6(4) ?
    C8 C1 C2 C3 . . . . -167.1(3) ?
    C10 N3 C15 C14 . . . . 167.6(2) ?
    C11 N3 C15 C14 . . . . -58.6(3) ?
    N3 C11 C12 C13 . . . . -59.2(3) ?
    C16 C17 C18 C19 . . . . -179.6(2) ?
    C1 C6 C5 C4 . . . . 9.4(5) ?
    S1 C6 C5 C4 . . . . -171.8(3) ?
    N3 C15 C14 C13 . . . . 56.7(4) ?
    C15 C14 C13 C12 . . . . -55.1(4) ?
    C11 C12 C13 C14 . . . . 55.6(4) ?
    C1 C2 C3 C4 . . . . -35.9(5) ?
    C2 C3 C4 C5 . . . . 50.3(6) ?
    C6 C5 C4 C3 . . . . -34.3(5) ?
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
    C17 H17A O1 . 0.97 2.54 3.035(4) 111.7 y
    C4 H4A Cg2 2_666 0.97 3.00 3.854(5) 148 y
    C11 H11A Cg2 2_555 0.97 2.76 3.408(3) 125 y
    C12 H12A Cg1 2_555 0.97 2.92 3.764(4) 146 y
