##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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     SHELXL-97
_journal_date_recd_electronic     2008-11-09
_journal_date_accepted     2008-11-11
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue     12
_journal_page_first     o2404
_journal_page_last     o2404
_journal_paper_category     QO
_journal_coeditor_code     AT2674
_publ_contact_author_name     'Prof. Zeng Xiao-Hua and Wang Hong-Mei'
_publ_contact_author_address
; Department of Medicinal Chemistry, Yunyang Medical College, Shiyan 442000
  P.R. China
;
_publ_contact_author_email     zengken@126.com
_publ_contact_author_fax     '86 719 8875328'
_publ_contact_author_phone     '86 719 8875301'
_publ_section_title
;\
2-(4-Bromophenoxy)-3-isopropyl-5,6,7,8-tetrahydro-1-benzothieno[2,3-<i>d</i>]\
pyrimidin-4(3<i>H</i>)-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
;
    'Chen, Li-Li' .
;
Department of Medicinal Chemistry
Yunyang Medical College
Shiyan 442000
People's Republic of China
;
    'Hu, Ting' .
;
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
;
data_I
_chemical_name_systematic
;
 2-(4-Bromo-phenoxy)-3-isopropyl-5,6,7,8-tetrahydro
-benzothieno[2,3-d]pyrimidin-4(3H)-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H19 Br N2 O2 S'
_chemical_formula_sum     'C19 H19 Br N2 O2 S'
_chemical_formula_weight     419.33
_chemical_melting_point     478K
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21'
_symmetry_space_group_name_Hall     'P 2yb'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     13.3957(7)
_cell_length_b     5.7366(3)
_cell_length_c     13.3956(7)
_cell_angle_alpha     90.00
_cell_angle_beta     115.5410(10)
_cell_angle_gamma     90.00
_cell_volume     928.81(8)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2048
_cell_measurement_theta_min     2.85
_cell_measurement_theta_max     24.54
_cell_measurement_temperature     298(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.10
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.499
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     428
_exptl_absorpt_coefficient_mu     2.340
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.6519
_exptl_absorpt_correction_T_max     0.7997
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     298(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     '\f and \w scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     5798
_diffrn_reflns_av_R_equivalents     0.1062
_diffrn_reflns_av_sigmaI/netI     0.1024
_diffrn_reflns_theta_min     1.68
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -6
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_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^ > 2sigma(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.
;
_reflns_number_total     3228
_reflns_number_gt     2346
_reflns_threshold_expression     'I>2\s(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0955
_refine_ls_R_factor_gt     0.0665
_refine_ls_wR_factor_gt     0.1702
_refine_ls_wR_factor_ref     0.2037
_refine_ls_goodness_of_fit_ref     1.074
_refine_ls_restrained_S_all     1.074
_refine_ls_number_reflns     3228
_refine_ls_number_parameters     228
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.1151P)^2^+0.0000P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.674
_refine_diff_density_min     -0.625
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983), 1424 Friedel pairs'
_refine_ls_abs_structure_Flack     0.00(8)
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'
    'Br' 'Br' -0.2901 2.4595
                         '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'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement     'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON (Spek, 2003)'
_computing_publication_material     'SHELXTL (Sheldrick, 1997)'
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
    Br Br1 0.84533(6) 0.7555(2) 0.71718(7) 0.0762(4) Uani d . 1 . .
    C C1 0.0942(6) 1.2447(18) 0.8813(6) 0.0534(18) Uani d . 1 . .
    H H1A 0.0444 1.3157 0.8118 0.064 Uiso calc R 1 . .
    H H1B 0.0650 1.0921 0.8853 0.064 Uiso calc R 1 . .
    C C2 0.0967(9) 1.390(3) 0.9738(10) 0.103(5) Uani d . 1 . .
    H H2A 0.0231 1.4514 0.9536 0.124 Uiso calc R 1 . .
    H H2B 0.1152 1.2908 1.0380 0.124 Uiso calc R 1 . .
    C C3 0.1719(9) 1.578(2) 1.0038(11) 0.093(4) Uani d . 1 . .
    H H3A 0.1730 1.6464 1.0704 0.111 Uiso calc R 1 . .
    H H3B 0.1416 1.6942 0.9459 0.111 Uiso calc R 1 . .
    C C4 0.2917(7) 1.537(2) 1.0246(7) 0.067(3) Uani d . 1 . .
    H H4A 0.3234 1.6797 1.0119 0.081 Uiso calc R 1 . .
    H H4B 0.3351 1.4885 1.1006 0.081 Uiso calc R 1 . .
    C C5 0.2930(6) 1.3513(13) 0.9472(6) 0.0460(19) Uani d . 1 . .
    C C6 0.2071(5) 1.2157(15) 0.8824(5) 0.046(2) Uani d . 1 . .
    C C7 0.2363(6) 1.0548(14) 0.8163(6) 0.0405(16) Uani d . 1 . .
    C C8 0.3446(6) 1.0816(16) 0.8335(6) 0.052(2) Uani d . 1 . .
    C C9 0.1666(6) 0.9073(15) 0.7312(6) 0.0457(18) Uani d . 1 . .
    C C10 0.3302(6) 0.8295(14) 0.7015(6) 0.047(2) Uani d . 1 . .
    C C11 0.1472(6) 0.6545(14) 0.5719(6) 0.0459(18) Uani d . 1 . .
    H H11 0.0726 0.6617 0.5683 0.055 Uiso calc R 1 . .
    C C12 0.1754(9) 0.3997(19) 0.5775(8) 0.079(3) Uani d . 1 . .
    H H12A 0.1906 0.3406 0.6497 0.119 Uiso calc R 1 . .
    H H12B 0.2395 0.3796 0.5638 0.119 Uiso calc R 1 . .
    H H12C 0.1142 0.3161 0.5228 0.119 Uiso calc R 1 . .
    C C13 0.1386(8) 0.767(2) 0.4657(6) 0.071(2) Uani d . 1 . .
    H H13A 0.2104 0.7707 0.4661 0.107 Uiso calc R 1 . .
    H H13B 0.1112 0.9233 0.4608 0.107 Uiso calc R 1 . .
    H H13C 0.0889 0.6784 0.4033 0.107 Uiso calc R 1 . .
    C C14 0.4794(6) 0.7242(18) 0.6612(7) 0.055(2) Uani d . 1 . .
    C C15 0.5512(8) 0.553(2) 0.7233(8) 0.073(3) Uani d . 1 . .
    H H15 0.5268 0.4320 0.7536 0.087 Uiso calc R 1 . .
    C C16 0.6596(8) 0.563(2) 0.7394(9) 0.074(3) Uani d . 1 . .
    H H16 0.7096 0.4498 0.7815 0.088 Uiso calc R 1 . .
    C C17 0.6938(5) 0.741(2) 0.6934(6) 0.061(2) Uani d . 1 . .
    C C18 0.6221(7) 0.9049(19) 0.6317(8) 0.066(2) Uani d . 1 . .
    H H18 0.6458 1.0245 0.6002 0.079 Uiso calc R 1 . .
    C C19 0.5134(8) 0.895(2) 0.6152(9) 0.073(3) Uani d . 1 . .
    H H19 0.4634 1.0073 0.5720 0.088 Uiso calc R 1 . .
    N N1 0.3955(5) 0.9634(13) 0.7793(6) 0.0527(17) Uani d . 1 . .
    N N2 0.2193(4) 0.7931(13) 0.6717(4) 0.0415(13) Uani d . 1 . .
    O O1 0.0683(4) 0.8637(12) 0.7061(5) 0.0664(19) Uani d . 1 . .
    O O2 0.3666(4) 0.7053(13) 0.6384(5) 0.072(2) Uani d . 1 . .
    S S1 0.41333(15) 1.2916(5) 0.93045(17) 0.0604(6) Uani d . 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
    Br1 0.0420(4) 0.1275(10) 0.0622(5) -0.0010(6) 0.0253(4) -0.0105(6)
    C1 0.048(4) 0.055(5) 0.061(4) -0.001(5) 0.027(3) 0.001(5)
    C2 0.063(6) 0.162(13) 0.089(8) -0.006(7) 0.037(6) -0.052(8)
    C3 0.079(7) 0.105(10) 0.106(9) -0.008(7) 0.051(7) -0.036(8)
    C4 0.059(5) 0.090(7) 0.043(4) 0.009(5) 0.013(4) -0.009(5)
    C5 0.045(4) 0.050(5) 0.038(4) 0.004(3) 0.014(3) 0.001(3)
    C6 0.039(4) 0.057(6) 0.036(3) 0.007(4) 0.011(3) 0.004(4)
    C7 0.032(3) 0.052(4) 0.033(3) 0.007(3) 0.010(3) 0.002(3)
    C8 0.033(4) 0.070(6) 0.043(4) -0.004(4) 0.006(3) -0.002(4)
    C9 0.037(4) 0.055(5) 0.040(4) -0.004(4) 0.012(3) 0.006(3)
    C10 0.038(4) 0.053(5) 0.049(4) 0.004(3) 0.018(3) -0.006(3)
    C11 0.037(4) 0.053(5) 0.044(4) -0.009(3) 0.013(3) -0.004(3)
    C12 0.100(8) 0.058(6) 0.061(6) -0.002(6) 0.016(6) 0.001(5)
    C13 0.083(6) 0.069(6) 0.044(4) 0.001(6) 0.011(4) 0.007(5)
    C14 0.039(4) 0.068(6) 0.061(4) -0.009(4) 0.024(3) -0.022(5)
    C15 0.054(5) 0.088(8) 0.076(7) -0.002(5) 0.028(5) 0.010(6)
    C16 0.050(5) 0.093(8) 0.076(6) 0.004(5) 0.027(5) 0.019(6)
    C17 0.034(3) 0.106(7) 0.043(4) 0.005(6) 0.016(3) -0.019(6)
    C18 0.049(5) 0.072(6) 0.074(6) 0.000(5) 0.023(5) 0.016(5)
    C19 0.048(5) 0.077(7) 0.084(7) 0.011(5) 0.019(5) 0.009(5)
    N1 0.034(3) 0.063(5) 0.057(4) -0.007(3) 0.016(3) -0.022(4)
    N2 0.031(3) 0.049(4) 0.043(3) -0.005(3) 0.013(2) 0.002(3)
    O1 0.033(3) 0.103(6) 0.062(3) -0.012(3) 0.018(2) -0.019(3)
    O2 0.039(3) 0.098(6) 0.079(4) -0.011(3) 0.025(3) -0.041(4)
    S1 0.0373(9) 0.0736(16) 0.0600(11) -0.0053(11) 0.0114(8) -0.0194(12)
_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
    Br1 C17 . 1.916(7) ?
    C1 C2 . 1.481(14) ?
    C1 C6 . 1.515(9) ?
    C1 H1A . 0.9700 ?
    C1 H1B . 0.9700 ?
    C2 C3 . 1.410(18) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 C4 . 1.523(14) ?
    C3 H3A . 0.9700 ?
    C3 H3B . 0.9700 ?
    C4 C5 . 1.492(12) ?
    C4 H4A . 0.9700 ?
    C4 H4B . 0.9700 ?
    C5 C6 . 1.350(11) ?
    C5 S1 . 1.754(8) ?
    C6 C7 . 1.445(10) ?
    C7 C8 . 1.375(10) ?
    C7 C9 . 1.404(11) ?
    C8 N1 . 1.370(10) ?
    C8 S1 . 1.719(9) ?
    C9 O1 . 1.236(9) ?
    C9 N2 . 1.431(10) ?
    C10 N1 . 1.287(10) ?
    C10 O2 . 1.347(9) ?
    C10 N2 . 1.378(8) ?
    C11 N2 . 1.497(9) ?
    C11 C12 . 1.504(14) ?
    C11 C13 . 1.521(12) ?
    C11 H11 . 0.9800 ?
    C12 H12A . 0.9600 ?
    C12 H12B . 0.9600 ?
    C12 H12C . 0.9600 ?
    C13 H13A . 0.9600 ?
    C13 H13B . 0.9600 ?
    C13 H13C . 0.9600 ?
    C14 C19 . 1.336(15) ?
    C14 C15 . 1.377(15) ?
    C14 O2 . 1.412(9) ?
    C15 C16 . 1.374(13) ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.370(15) ?
    C16 H16 . 0.9300 ?
    C17 C18 . 1.342(14) ?
    C18 C19 . 1.377(12) ?
    C18 H18 . 0.9300 ?
    C19 H19 . 0.9300 ?
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
    C2 C1 C6 . . 113.0(7) ?
    C2 C1 H1A . . 109.0 ?
    C6 C1 H1A . . 109.0 ?
    C2 C1 H1B . . 109.0 ?
    C6 C1 H1B . . 109.0 ?
    H1A C1 H1B . . 107.8 ?
    C3 C2 C1 . . 115.1(10) ?
    C3 C2 H2A . . 108.5 ?
    C1 C2 H2A . . 108.5 ?
    C3 C2 H2B . . 108.5 ?
    C1 C2 H2B . . 108.5 ?
    H2A C2 H2B . . 107.5 ?
    C2 C3 C4 . . 120.1(11) ?
    C2 C3 H3A . . 107.3 ?
    C4 C3 H3A . . 107.3 ?
    C2 C3 H3B . . 107.3 ?
    C4 C3 H3B . . 107.3 ?
    H3A C3 H3B . . 106.9 ?
    C5 C4 C3 . . 108.0(8) ?
    C5 C4 H4A . . 110.1 ?
    C3 C4 H4A . . 110.1 ?
    C5 C4 H4B . . 110.1 ?
    C3 C4 H4B . . 110.1 ?
    H4A C4 H4B . . 108.4 ?
    C6 C5 C4 . . 126.6(7) ?
    C6 C5 S1 . . 112.4(5) ?
    C4 C5 S1 . . 121.0(6) ?
    C5 C6 C7 . . 112.3(6) ?
    C5 C6 C1 . . 120.9(7) ?
    C7 C6 C1 . . 126.7(7) ?
    C8 C7 C9 . . 119.2(7) ?
    C8 C7 C6 . . 111.8(7) ?
    C9 C7 C6 . . 128.4(6) ?
    N1 C8 C7 . . 125.8(7) ?
    N1 C8 S1 . . 121.3(5) ?
    C7 C8 S1 . . 112.8(6) ?
    O1 C9 C7 . . 126.9(7) ?
    O1 C9 N2 . . 118.7(7) ?
    C7 C9 N2 . . 114.4(6) ?
    N1 C10 O2 . . 121.4(6) ?
    N1 C10 N2 . . 126.6(7) ?
    O2 C10 N2 . . 112.0(6) ?
    N2 C11 C12 . . 114.8(7) ?
    N2 C11 C13 . . 111.6(7) ?
    C12 C11 C13 . . 112.1(8) ?
    N2 C11 H11 . . 105.8 ?
    C12 C11 H11 . . 105.8 ?
    C13 C11 H11 . . 105.8 ?
    C11 C12 H12A . . 109.5 ?
    C11 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    C11 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    C11 C13 H13A . . 109.5 ?
    C11 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    C11 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    C19 C14 C15 . . 121.0(8) ?
    C19 C14 O2 . . 120.1(9) ?
    C15 C14 O2 . . 118.6(9) ?
    C16 C15 C14 . . 118.6(10) ?
    C16 C15 H15 . . 120.7 ?
    C14 C15 H15 . . 120.7 ?
    C17 C16 C15 . . 119.9(10) ?
    C17 C16 H16 . . 120.1 ?
    C15 C16 H16 . . 120.1 ?
    C18 C17 C16 . . 120.6(7) ?
    C18 C17 Br1 . . 119.9(8) ?
    C16 C17 Br1 . . 119.5(8) ?
    C17 C18 C19 . . 119.7(10) ?
    C17 C18 H18 . . 120.1 ?
    C19 C18 H18 . . 120.1 ?
    C14 C19 C18 . . 120.2(9) ?
    C14 C19 H19 . . 119.9 ?
    C18 C19 H19 . . 119.9 ?
    C10 N1 C8 . . 113.9(6) ?
    C10 N2 C9 . . 119.9(6) ?
    C10 N2 C11 . . 122.7(6) ?
    C9 N2 C11 . . 117.2(5) ?
    C10 O2 C14 . . 117.8(6) ?
    C8 S1 C5 . . 90.6(4) ?
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
    C6 C1 C2 C3 . . . . 36.3(16) ?
    C1 C2 C3 C4 . . . . -50.1(18) ?
    C2 C3 C4 C5 . . . . 34.6(16) ?
    C3 C4 C5 C6 . . . . -9.8(13) ?
    C3 C4 C5 S1 . . . . 169.1(8) ?
    C4 C5 C6 C7 . . . . 179.3(8) ?
    S1 C5 C6 C7 . . . . 0.4(8) ?
    C4 C5 C6 C1 . . . . 1.0(12) ?
    S1 C5 C6 C1 . . . . -177.9(6) ?
    C2 C1 C6 C5 . . . . -13.3(13) ?
    C2 C1 C6 C7 . . . . 168.6(10) ?
    C5 C6 C7 C8 . . . . -1.3(10) ?
    C1 C6 C7 C8 . . . . 176.9(7) ?
    C5 C6 C7 C9 . . . . -172.1(8) ?
    C1 C6 C7 C9 . . . . 6.1(13) ?
    C9 C7 C8 N1 . . . . -4.8(13) ?
    C6 C7 C8 N1 . . . . -176.6(8) ?
    C9 C7 C8 S1 . . . . 173.4(6) ?
    C6 C7 C8 S1 . . . . 1.6(9) ?
    C8 C7 C9 O1 . . . . 179.4(8) ?
    C6 C7 C9 O1 . . . . -10.4(14) ?
    C8 C7 C9 N2 . . . . 1.5(11) ?
    C6 C7 C9 N2 . . . . 171.7(7) ?
    C19 C14 C15 C16 . . . . 1.5(15) ?
    O2 C14 C15 C16 . . . . 175.9(9) ?
    C14 C15 C16 C17 . . . . -0.4(16) ?
    C15 C16 C17 C18 . . . . -0.6(16) ?
    C15 C16 C17 Br1 . . . . 179.7(8) ?
    C16 C17 C18 C19 . . . . 0.6(15) ?
    Br1 C17 C18 C19 . . . . -179.7(8) ?
    C15 C14 C19 C18 . . . . -1.6(16) ?
    O2 C14 C19 C18 . . . . -175.9(9) ?
    C17 C18 C19 C14 . . . . 0.5(16) ?
    O2 C10 N1 C8 . . . . 178.4(7) ?
    N2 C10 N1 C8 . . . . -1.7(13) ?
    C7 C8 N1 C10 . . . . 4.8(13) ?
    S1 C8 N1 C10 . . . . -173.3(6) ?
    N1 C10 N2 C9 . . . . -1.2(12) ?
    O2 C10 N2 C9 . . . . 178.8(7) ?
    N1 C10 N2 C11 . . . . 173.0(8) ?
    O2 C10 N2 C11 . . . . -7.0(10) ?
    O1 C9 N2 C10 . . . . -176.8(7) ?
    C7 C9 N2 C10 . . . . 1.2(10) ?
    O1 C9 N2 C11 . . . . 8.7(10) ?
    C7 C9 N2 C11 . . . . -173.3(7) ?
    C12 C11 N2 C10 . . . . 66.0(10) ?
    C13 C11 N2 C10 . . . . -63.0(10) ?
    C12 C11 N2 C9 . . . . -119.6(9) ?
    C13 C11 N2 C9 . . . . 111.4(8) ?
    N1 C10 O2 C14 . . . . 0.8(13) ?
    N2 C10 O2 C14 . . . . -179.2(7) ?
    C19 C14 O2 C10 . . . . -86.5(11) ?
    C15 C14 O2 C10 . . . . 99.1(10) ?
    N1 C8 S1 C5 . . . . 177.1(8) ?
    C7 C8 S1 C5 . . . . -1.2(7) ?
    C6 C5 S1 C8 . . . . 0.4(6) ?
    C4 C5 S1 C8 . . . . -178.6(7) ?
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
    C11 H11 O1 . 0.98 2.20 2.726(10) 112.1 y
    C12 H12B O2 . 0.96 2.43 2.915(13) 110.7 y
    C13 H13A O2 . 0.96 2.38 2.951(10) 117.4 y
    C12 H12B Cg1 . 0.96 2.92 3.854(11) 165 y
    C12 H12B Cg2 . 0.96 2.71 3.434(11) 133 y