##############################################################################
###                                                                        ###
###        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 2.1.    #
#                                                                            #
# 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/  #
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##############################################################################
                                             
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2006-06-30
_journal_date_accepted     2006-07-13
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue      8
_journal_page_first     o3428
_journal_page_last     o3429
_journal_paper_category     EO
_journal_coeditor_code     IS2063
_publ_contact_author_name     'Prof. MingWu Ding'
_publ_contact_author_address
; Key Laboratory of Pesticide and Chemical Biology of Ministry of Education
  College of Chemistry
  Central China Normal University
  Wuhan  430079
  China
;
_publ_contact_author_email     ding2005711@yahoo.com.cn
_publ_contact_author_fax     '86 27 67867706'
_publ_contact_author_phone     '86 27 67866229'
_publ_section_title
;\
2-Morpholino-3-p-tolylbenzo[4,5]thieno[3,2-d]pyrimidin-\
4(3H)-one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Sheng-Zhen Xu' .
; Key Laboratory of Pesticide and Chemical Biology of Ministry of Education
  College of Chemistry
  Central China Normal University
  Wuhan 430079
  People's Republic of China
;
    'Yang-Gen Hu' .
; Key Laboratory of Pesticide and Chemical Biology of Ministry of Education
  College of Chemistry
  Central China Normal University
  Wuhan 430079
  People's Republic of China
;
    'Ming-Guo Liu' .
; Key Laboratory of Pesticide and Chemical Biology of Ministry of Education
  College of Chemistry
  Central China Normal University
  Wuhan 430079
  People's Republic of China
;
    'Ming-Wu Ding' .
; Key Laboratory of Pesticide and Chemical Biology of Ministry of Education
  College of Chemistry
  Central China Normal University
  Wuhan 430079
  People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2-Morpholino-3-p-tolylbenzo[4,5]thieno[3,2-d]pyrimidin-4(3H)-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C21 H19 N3 O2 S'
_chemical_formula_sum     'C21 H19 N3 O2 S'
_chemical_formula_iupac     'C21 H19 N3 O2 S'
_chemical_formula_weight     377.45
_chemical_melting_point     469
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     16.693(3)
_cell_length_b     12.970(2)
_cell_length_c     17.392(3)
_cell_angle_alpha     90.00
_cell_angle_beta     94.002(3)
_cell_angle_gamma     90.00
_cell_volume     3756.6(12)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     7182
_cell_measurement_theta_min     2.27
_cell_measurement_theta_max     24.55
_cell_measurement_temperature     273(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.26
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.335
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1584
_exptl_absorpt_coefficient_mu     0.194
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_correction_T_min     0.9442
_exptl_absorpt_correction_T_max     0.9771
_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 4K CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     38099
_diffrn_reflns_av_R_equivalents     0.1054
_diffrn_reflns_av_sigmaI/netI     0.0676
_diffrn_reflns_theta_min     1.63
_diffrn_reflns_theta_max     27.00
_diffrn_reflns_theta_full     27.00
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -21
_diffrn_reflns_limit_h_max     21
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     16
_diffrn_reflns_limit_l_min     -22
_diffrn_reflns_limit_l_max     22
_diffrn_standards_number     0
_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     8200
_reflns_number_gt     5715
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0785
_refine_ls_R_factor_gt     0.0528
_refine_ls_wR_factor_gt     0.1164
_refine_ls_wR_factor_ref     0.1257
_refine_ls_goodness_of_fit_ref     0.955
_refine_ls_restrained_S_all     0.955
_refine_ls_number_reflns     8200
_refine_ls_number_parameters     489
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0634P)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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.309
_refine_diff_density_min     -0.369
_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'
_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
    C C1 0.50092(11) 0.13508(14) 1.03319(10) 0.0362(4) Uani d . 1 . .
    C C2 0.43206(11) 0.18288(15) 1.00042(12) 0.0447(5) Uani d . 1 . .
    H H2 0.4319 0.2127 0.9518 0.054 Uiso calc R 1 . .
    C C3 0.36437(12) 0.18545(16) 1.04084(13) 0.0515(5) Uani d . 1 . .
    H H3 0.3181 0.2170 1.0192 0.062 Uiso calc R 1 . .
    C C4 0.36409(12) 0.14155(16) 1.11367(13) 0.0518(5) Uani d . 1 . .
    H H4 0.3179 0.1454 1.1406 0.062 Uiso calc R 1 . .
    C C5 0.43073(12) 0.09272(16) 1.14648(12) 0.0485(5) Uani d . 1 . .
    H H5 0.4299 0.0623 1.1949 0.058 Uiso calc R 1 . .
    C C6 0.49967(11) 0.08953(15) 1.10593(10) 0.0397(4) Uani d . 1 . .
    C C7 0.63087(11) 0.07026(15) 1.05104(10) 0.0391(4) Uani d . 1 . .
    C C8 0.57856(11) 0.12311(14) 1.00257(10) 0.0353(4) Uani d . 1 . .
    C C9 0.71075(11) 0.04804(16) 1.03219(11) 0.0418(5) Uani d . 1 . .
    C C10 0.66886(11) 0.13785(14) 0.91147(10) 0.0355(4) Uani d . 1 . .
    C C11 0.80815(10) 0.06983(14) 0.93547(10) 0.0356(4) Uani d . 1 . .
    C C12 0.83746(11) -0.02918(15) 0.92986(11) 0.0433(5) Uani d . 1 . .
    H H12 0.8056 -0.0854 0.9408 0.052 Uiso calc R 1 . .
    C C13 0.91451(12) -0.04411(17) 0.90782(11) 0.0482(5) Uani d . 1 . .
    H H13 0.9343 -0.1109 0.9046 0.058 Uiso calc R 1 . .
    C C14 0.96300(11) 0.03833(18) 0.89042(11) 0.0472(5) Uani d . 1 . .
    C C15 0.93225(12) 0.13630(17) 0.89782(12) 0.0503(5) Uani d . 1 . .
    H H15 0.9639 0.1927 0.8870 0.060 Uiso calc R 1 . .
    C C16 0.85570(11) 0.15302(15) 0.92087(11) 0.0436(5) Uani d . 1 . .
    H H16 0.8366 0.2198 0.9264 0.052 Uiso calc R 1 . .
    C C17 1.04699(13) 0.0206(2) 0.86526(15) 0.0771(8) Uani d . 1 . .
    H H17A 1.0622 0.0775 0.8341 0.116 Uiso calc R 1 . .
    H H17B 1.0480 -0.0419 0.8358 0.116 Uiso calc R 1 . .
    H H17C 1.0839 0.0150 0.9099 0.116 Uiso calc R 1 . .
    C C18 0.71111(13) 0.10310(17) 0.78116(11) 0.0520(5) Uani d . 1 . .
    H H18A 0.6626 0.0702 0.7591 0.062 Uiso calc R 1 . .
    H H18B 0.7468 0.0500 0.8029 0.062 Uiso calc R 1 . .
    C C19 0.75160(14) 0.1616(2) 0.71917(13) 0.0660(7) Uani d . 1 . .
    H H19A 0.8026 0.1884 0.7407 0.079 Uiso calc R 1 . .
    H H19B 0.7625 0.1145 0.6778 0.079 Uiso calc R 1 . .
    C C20 0.64053(13) 0.25925(18) 0.80909(13) 0.0571(6) Uani d . 1 . .
    H H20A 0.6286 0.3076 0.8493 0.069 Uiso calc R 1 . .
    H H20B 0.5903 0.2319 0.7863 0.069 Uiso calc R 1 . .
    C C21 0.68572(15) 0.3125(2) 0.74876(13) 0.0706(7) Uani d . 1 . .
    H H21A 0.6537 0.3693 0.7272 0.085 Uiso calc R 1 . .
    H H21B 0.7352 0.3408 0.7726 0.085 Uiso calc R 1 . .
    C C22 0.04557(11) 0.39932(15) 1.06504(10) 0.0389(4) Uani d . 1 . .
    C C23 -0.00580(12) 0.31493(16) 1.05555(12) 0.0500(5) Uani d . 1 . .
    H H23 0.0037 0.2643 1.0194 0.060 Uiso calc R 1 . .
    C C24 -0.07049(14) 0.30686(18) 1.09984(13) 0.0603(6) Uani d . 1 . .
    H H24 -0.1048 0.2505 1.0936 0.072 Uiso calc R 1 . .
    C C25 -0.08516(14) 0.38240(19) 1.15395(13) 0.0606(6) Uani d . 1 . .
    H H25 -0.1292 0.3756 1.1835 0.073 Uiso calc R 1 . .
    C C26 -0.03589(13) 0.46675(18) 1.16459(12) 0.0539(6) Uani d . 1 . .
    H H26 -0.0462 0.5171 1.2006 0.065 Uiso calc R 1 . .
    C C27 0.03017(12) 0.47502(15) 1.11988(10) 0.0429(5) Uani d . 1 . .
    C C28 0.11560(11) 0.42526(14) 1.02542(10) 0.0375(4) Uani d . 1 . .
    C C29 0.15037(11) 0.51506(15) 1.05112(10) 0.0399(4) Uani d . 1 . .
    C C30 0.22160(12) 0.55416(15) 1.02124(11) 0.0430(5) Uani d . 1 . .
    C C31 0.20613(11) 0.40402(14) 0.93475(10) 0.0369(4) Uani d . 1 . .
    C C32 0.32649(11) 0.51696(14) 0.93424(11) 0.0389(4) Uani d . 1 . .
    C C33 0.33859(13) 0.60996(16) 0.89829(12) 0.0517(5) Uani d . 1 . .
    H H33 0.2979 0.6590 0.8936 0.062 Uiso calc R 1 . .
    C C34 0.41213(16) 0.62882(19) 0.86945(13) 0.0643(7) Uani d . 1 . .
    H H34 0.4204 0.6915 0.8453 0.077 Uiso calc R 1 . .
    C C35 0.47376(14) 0.5580(2) 0.87522(13) 0.0629(7) Uani d . 1 . .
    C C36 0.46084(13) 0.4667(2) 0.91385(13) 0.0605(6) Uani d . 1 . .
    H H36 0.5019 0.4183 0.9197 0.073 Uiso calc R 1 . .
    C C37 0.38806(12) 0.44641(16) 0.94382(12) 0.0477(5) Uani d . 1 . .
    H H37 0.3806 0.3853 0.9704 0.057 Uiso calc R 1 . .
    C C38 0.55412(16) 0.5789(3) 0.84237(17) 0.0983(11) Uani d . 1 . .
    H H38A 0.5949 0.5859 0.8838 0.147 Uiso calc R 1 . .
    H H38B 0.5508 0.6415 0.8128 0.147 Uiso calc R 1 . .
    H H38C 0.5675 0.5226 0.8098 0.147 Uiso calc R 1 . .
    C C39 0.24506(13) 0.40434(16) 0.80091(10) 0.0482(5) Uani d . 1 . .
    H H39A 0.2706 0.4706 0.8111 0.058 Uiso calc R 1 . .
    H H39B 0.1927 0.4164 0.7747 0.058 Uiso calc R 1 . .
    C C40 0.29548(14) 0.34048(18) 0.75062(12) 0.0595(6) Uani d . 1 . .
    H H40A 0.3008 0.3760 0.7022 0.071 Uiso calc R 1 . .
    H H40B 0.3488 0.3321 0.7758 0.071 Uiso calc R 1 . .
    C C41 0.19996(13) 0.24839(15) 0.85862(12) 0.0484(5) Uani d . 1 . .
    H H41A 0.1462 0.2560 0.8343 0.058 Uiso calc R 1 . .
    H H41B 0.1964 0.2111 0.9066 0.058 Uiso calc R 1 . .
    C C42 0.25164(14) 0.18962(17) 0.80631(13) 0.0594(6) Uani d . 1 . .
    H H42A 0.3041 0.1786 0.8325 0.071 Uiso calc R 1 . .
    H H42B 0.2277 0.1226 0.7953 0.071 Uiso calc R 1 . .
    N N1 0.59676(9) 0.15789(12) 0.93155(8) 0.0377(4) Uani d . 1 . .
    N N2 0.72663(8) 0.08502(12) 0.95804(8) 0.0359(4) Uani d . 1 . .
    N N3 0.69115(9) 0.17522(12) 0.84154(8) 0.0406(4) Uani d . 1 . .
    N N4 0.14278(9) 0.36906(12) 0.96545(8) 0.0389(4) Uani d . 1 . .
    N N5 0.24864(9) 0.49122(11) 0.96108(8) 0.0375(4) Uani d . 1 . .
    N N6 0.23573(9) 0.35016(12) 0.87401(8) 0.0391(4) Uani d . 1 . .
    O O1 0.76216(8) 0.00462(13) 1.07344(8) 0.0608(4) Uani d . 1 . .
    O O2 0.70400(10) 0.24416(15) 0.68865(9) 0.0724(5) Uani d . 1 . .
    O O3 0.25903(9) 0.63063(12) 1.04315(9) 0.0643(4) Uani d . 1 . .
    O O4 0.26085(10) 0.24230(13) 0.73592(8) 0.0650(4) Uani d . 1 . .
    S S1 0.59071(3) 0.03124(5) 1.13571(3) 0.05062(16) Uani d . 1 . .
    S S2 0.10069(3) 0.57406(4) 1.12392(3) 0.04899(16) 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
    C1 C2 . 1.393(3) ?
    C1 C6 . 1.398(3) ?
    C1 C8 . 1.443(2) ?
    C2 C3 . 1.372(3) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.389(3) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.370(3) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.392(2) ?
    C5 H5 . 0.9300 ?
    C6 S1 . 1.743(2) ?
    C7 C8 . 1.357(3) ?
    C7 C9 . 1.425(2) ?
    C7 S1 . 1.7355(18) yes
    C8 N1 . 1.369(2) ?
    C9 O1 . 1.218(2) ?
    C9 N2 . 1.418(2) ?
    C10 N1 . 1.303(2) ?
    C10 N3 . 1.384(2) ?
    C10 N2 . 1.395(2) ?
    C11 C16 . 1.374(3) ?
    C11 C12 . 1.380(3) ?
    C11 N2 . 1.456(2) ?
    C12 C13 . 1.381(3) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.387(3) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.380(3) ?
    C14 C17 . 1.515(3) ?
    C15 C16 . 1.383(3) ?
    C15 H15 . 0.9300 ?
    C16 H16 . 0.9300 ?
    C17 H17A . 0.9600 ?
    C17 H17B . 0.9600 ?
    C17 H17C . 0.9600 ?
    C18 N3 . 1.462(2) ?
    C18 C19 . 1.515(3) ?
    C18 H18A . 0.9700 ?
    C18 H18B . 0.9700 ?
    C19 O2 . 1.415(3) ?
    C19 H19A . 0.9700 ?
    C19 H19B . 0.9700 ?
    C20 N3 . 1.467(2) ?
    C20 C21 . 1.503(3) ?
    C20 H20A . 0.9700 ?
    C20 H20B . 0.9700 ?
    C21 O2 . 1.420(3) ?
    C21 H21A . 0.9700 ?
    C21 H21B . 0.9700 ?
    C22 C23 . 1.393(3) ?
    C22 C27 . 1.405(3) ?
    C22 C28 . 1.438(3) ?
    C23 C24 . 1.374(3) ?
    C23 H23 . 0.9300 ?
    C24 C25 . 1.392(3) ?
    C24 H24 . 0.9300 ?
    C25 C26 . 1.373(3) ?
    C25 H25 . 0.9300 ?
    C26 C27 . 1.397(3) ?
    C26 H26 . 0.9300 ?
    C27 S2 . 1.741(2) yes
    C28 C29 . 1.363(3) ?
    C28 N4 . 1.375(2) ?
    C29 C30 . 1.424(3) ?
    C29 S2 . 1.7387(18) yes
    C30 O3 . 1.219(2) ?
    C30 N5 . 1.425(2) ?
    C31 N4 . 1.299(2) ?
    C31 N6 . 1.386(2) ?
    C31 N5 . 1.395(2) ?
    C32 C37 . 1.377(3) ?
    C32 C33 . 1.380(3) ?
    C32 N5 . 1.450(2) ?
    C33 C34 . 1.380(3) ?
    C33 H33 . 0.9300 ?
    C34 C35 . 1.378(3) ?
    C34 H34 . 0.9300 ?
    C35 C36 . 1.385(3) ?
    C35 C38 . 1.519(3) ?
    C36 C37 . 1.380(3) ?
    C36 H36 . 0.9300 ?
    C37 H37 . 0.9300 ?
    C38 H38A . 0.9600 ?
    C38 H38B . 0.9600 ?
    C38 H38C . 0.9600 ?
    C39 N6 . 1.471(2) ?
    C39 C40 . 1.504(3) ?
    C39 H39A . 0.9700 ?
    C39 H39B . 0.9700 ?
    C40 O4 . 1.414(3) ?
    C40 H40A . 0.9700 ?
    C40 H40B . 0.9700 ?
    C41 N6 . 1.466(2) ?
    C41 C42 . 1.504(3) ?
    C41 H41A . 0.9700 ?
    C41 H41B . 0.9700 ?
    C42 O4 . 1.420(3) ?
    C42 H42A . 0.9700 ?
    C42 H42B . 0.9700 ?
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 . . 119.64(17) ?
    C2 C1 C8 . . 129.32(17) ?
    C6 C1 C8 . . 111.04(16) ?
    C3 C2 C1 . . 119.13(19) ?
    C3 C2 H2 . . 120.4 ?
    C1 C2 H2 . . 120.4 ?
    C2 C3 C4 . . 120.8(2) ?
    C2 C3 H3 . . 119.6 ?
    C4 C3 H3 . . 119.6 ?
    C5 C4 C3 . . 121.02(19) ?
    C5 C4 H4 . . 119.5 ?
    C3 C4 H4 . . 119.5 ?
    C4 C5 C6 . . 118.61(19) ?
    C4 C5 H5 . . 120.7 ?
    C6 C5 H5 . . 120.7 ?
    C5 C6 C1 . . 120.75(18) ?
    C5 C6 S1 . . 126.64(16) yes
    C1 C6 S1 . . 112.61(13) yes
    C8 C7 C9 . . 122.10(16) ?
    C8 C7 S1 . . 113.86(14) yes
    C9 C7 S1 . . 124.02(14) yes
    C7 C8 N1 . . 123.60(16) ?
    C7 C8 C1 . . 112.38(16) ?
    N1 C8 C1 . . 123.99(16) ?
    O1 C9 N2 . . 121.56(17) ?
    O1 C9 C7 . . 126.20(18) ?
    N2 C9 C7 . . 112.22(16) ?
    N1 C10 N3 . . 118.42(16) ?
    N1 C10 N2 . . 123.81(15) ?
    N3 C10 N2 . . 117.69(15) ?
    C16 C11 C12 . . 120.37(17) ?
    C16 C11 N2 . . 120.44(16) ?
    C12 C11 N2 . . 119.18(16) ?
    C11 C12 C13 . . 119.45(19) ?
    C11 C12 H12 . . 120.3 ?
    C13 C12 H12 . . 120.3 ?
    C12 C13 C14 . . 121.42(19) ?
    C12 C13 H13 . . 119.3 ?
    C14 C13 H13 . . 119.3 ?
    C15 C14 C13 . . 117.58(18) ?
    C15 C14 C17 . . 121.6(2) ?
    C13 C14 C17 . . 120.8(2) ?
    C14 C15 C16 . . 121.92(19) ?
    C14 C15 H15 . . 119.0 ?
    C16 C15 H15 . . 119.0 ?
    C11 C16 C15 . . 119.21(18) ?
    C11 C16 H16 . . 120.4 ?
    C15 C16 H16 . . 120.4 ?
    C14 C17 H17A . . 109.5 ?
    C14 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    C14 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    N3 C18 C19 . . 109.04(18) ?
    N3 C18 H18A . . 109.9 ?
    C19 C18 H18A . . 109.9 ?
    N3 C18 H18B . . 109.9 ?
    C19 C18 H18B . . 109.9 ?
    H18A C18 H18B . . 108.3 ?
    O2 C19 C18 . . 112.28(18) ?
    O2 C19 H19A . . 109.1 ?
    C18 C19 H19A . . 109.1 ?
    O2 C19 H19B . . 109.1 ?
    C18 C19 H19B . . 109.1 ?
    H19A C19 H19B . . 107.9 ?
    N3 C20 C21 . . 107.85(17) ?
    N3 C20 H20A . . 110.1 ?
    C21 C20 H20A . . 110.1 ?
    N3 C20 H20B . . 110.1 ?
    C21 C20 H20B . . 110.1 ?
    H20A C20 H20B . . 108.5 ?
    O2 C21 C20 . . 111.8(2) ?
    O2 C21 H21A . . 109.3 ?
    C20 C21 H21A . . 109.3 ?
    O2 C21 H21B . . 109.3 ?
    C20 C21 H21B . . 109.3 ?
    H21A C21 H21B . . 107.9 ?
    C23 C22 C27 . . 119.30(18) ?
    C23 C22 C28 . . 129.90(18) ?
    C27 C22 C28 . . 110.80(17) ?
    C24 C23 C22 . . 119.7(2) ?
    C24 C23 H23 . . 120.2 ?
    C22 C23 H23 . . 120.2 ?
    C23 C24 C25 . . 120.5(2) ?
    C23 C24 H24 . . 119.7 ?
    C25 C24 H24 . . 119.7 ?
    C26 C25 C24 . . 121.3(2) ?
    C26 C25 H25 . . 119.3 ?
    C24 C25 H25 . . 119.3 ?
    C25 C26 C27 . . 118.3(2) ?
    C25 C26 H26 . . 120.8 ?
    C27 C26 H26 . . 120.8 ?
    C26 C27 C22 . . 120.86(19) ?
    C26 C27 S2 . . 126.31(17) yes
    C22 C27 S2 . . 112.83(14) yes
    C29 C28 N4 . . 123.11(17) ?
    C29 C28 C22 . . 112.63(17) ?
    N4 C28 C22 . . 124.18(17) ?
    C28 C29 C30 . . 122.15(17) ?
    C28 C29 S2 . . 113.65(14) yes
    C30 C29 S2 . . 124.19(15) yes
    O3 C30 C29 . . 126.76(18) ?
    O3 C30 N5 . . 120.93(18) ?
    C29 C30 N5 . . 112.30(16) ?
    N4 C31 N6 . . 118.75(17) ?
    N4 C31 N5 . . 123.92(16) ?
    N6 C31 N5 . . 117.29(16) ?
    C37 C32 C33 . . 120.27(19) ?
    C37 C32 N5 . . 119.07(17) ?
    C33 C32 N5 . . 120.65(17) ?
    C32 C33 C34 . . 118.8(2) ?
    C32 C33 H33 . . 120.6 ?
    C34 C33 H33 . . 120.6 ?
    C35 C34 C33 . . 122.3(2) ?
    C35 C34 H34 . . 118.9 ?
    C33 C34 H34 . . 118.9 ?
    C34 C35 C36 . . 117.7(2) ?
    C34 C35 C38 . . 121.9(2) ?
    C36 C35 C38 . . 120.5(3) ?
    C37 C36 C35 . . 121.2(2) ?
    C37 C36 H36 . . 119.4 ?
    C35 C36 H36 . . 119.4 ?
    C32 C37 C36 . . 119.8(2) ?
    C32 C37 H37 . . 120.1 ?
    C36 C37 H37 . . 120.1 ?
    C35 C38 H38A . . 109.5 ?
    C35 C38 H38B . . 109.5 ?
    H38A C38 H38B . . 109.5 ?
    C35 C38 H38C . . 109.5 ?
    H38A C38 H38C . . 109.5 ?
    H38B C38 H38C . . 109.5 ?
    N6 C39 C40 . . 109.70(17) ?
    N6 C39 H39A . . 109.7 ?
    C40 C39 H39A . . 109.7 ?
    N6 C39 H39B . . 109.7 ?
    C40 C39 H39B . . 109.7 ?
    H39A C39 H39B . . 108.2 ?
    O4 C40 C39 . . 111.27(18) ?
    O4 C40 H40A . . 109.4 ?
    C39 C40 H40A . . 109.4 ?
    O4 C40 H40B . . 109.4 ?
    C39 C40 H40B . . 109.4 ?
    H40A C40 H40B . . 108.0 ?
    N6 C41 C42 . . 108.87(17) ?
    N6 C41 H41A . . 109.9 ?
    C42 C41 H41A . . 109.9 ?
    N6 C41 H41B . . 109.9 ?
    C42 C41 H41B . . 109.9 ?
    H41A C41 H41B . . 108.3 ?
    O4 C42 C41 . . 112.27(18) ?
    O4 C42 H42A . . 109.2 ?
    C41 C42 H42A . . 109.2 ?
    O4 C42 H42B . . 109.2 ?
    C41 C42 H42B . . 109.2 ?
    H42A C42 H42B . . 107.9 ?
    C10 N1 C8 . . 116.34(15) ?
    C10 N2 C9 . . 121.91(14) ?
    C10 N2 C11 . . 122.09(14) ?
    C9 N2 C11 . . 115.91(14) ?
    C10 N3 C18 . . 119.72(16) ?
    C10 N3 C20 . . 114.52(15) ?
    C18 N3 C20 . . 110.67(16) ?
    C31 N4 C28 . . 116.60(16) ?
    C31 N5 C30 . . 121.69(15) ?
    C31 N5 C32 . . 121.85(15) ?
    C30 N5 C32 . . 116.19(15) ?
    C31 N6 C41 . . 115.52(15) ?
    C31 N6 C39 . . 118.89(15) ?
    C41 N6 C39 . . 109.81(15) ?
    C19 O2 C21 . . 109.90(17) ?
    C40 O4 C42 . . 110.18(16) ?
    C7 S1 C6 . . 90.10(9) yes
    C29 S2 C27 . . 90.08(9) yes
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 . . . . 0.8(3) ?
    C8 C1 C2 C3 . . . . -179.65(19) ?
    C1 C2 C3 C4 . . . . 0.3(3) ?
    C2 C3 C4 C5 . . . . -1.3(3) ?
    C3 C4 C5 C6 . . . . 1.2(3) ?
    C4 C5 C6 C1 . . . . -0.1(3) ?
    C4 C5 C6 S1 . . . . -179.48(16) no
    C2 C1 C6 C5 . . . . -1.0(3) ?
    C8 C1 C6 C5 . . . . 179.45(17) ?
    C2 C1 C6 S1 . . . . 178.53(14) no
    C8 C1 C6 S1 . . . . -1.1(2) no
    C9 C7 C8 N1 . . . . 1.2(3) ?
    S1 C7 C8 N1 . . . . -177.64(14) no
    C9 C7 C8 C1 . . . . 179.10(17) ?
    S1 C7 C8 C1 . . . . 0.2(2) no
    C2 C1 C8 C7 . . . . -179.01(19) ?
    C6 C1 C8 C7 . . . . 0.5(2) ?
    C2 C1 C8 N1 . . . . -1.1(3) ?
    C6 C1 C8 N1 . . . . 178.40(16) ?
    C8 C7 C9 O1 . . . . 177.1(2) ?
    S1 C7 C9 O1 . . . . -4.2(3) no
    C8 C7 C9 N2 . . . . -1.4(3) ?
    S1 C7 C9 N2 . . . . 177.31(14) no
    C16 C11 C12 C13 . . . . -1.4(3) ?
    N2 C11 C12 C13 . . . . 179.44(16) ?
    C11 C12 C13 C14 . . . . -0.6(3) ?
    C12 C13 C14 C15 . . . . 1.6(3) ?
    C12 C13 C14 C17 . . . . -179.15(19) ?
    C13 C14 C15 C16 . . . . -0.7(3) ?
    C17 C14 C15 C16 . . . . -179.9(2) ?
    C12 C11 C16 C15 . . . . 2.3(3) ?
    N2 C11 C16 C15 . . . . -178.53(17) ?
    C14 C15 C16 C11 . . . . -1.2(3) ?
    N3 C18 C19 O2 . . . . -56.0(2) ?
    N3 C20 C21 O2 . . . . 60.0(2) ?
    C27 C22 C23 C24 . . . . -0.1(3) ?
    C28 C22 C23 C24 . . . . -179.1(2) ?
    C22 C23 C24 C25 . . . . 0.1(3) ?
    C23 C24 C25 C26 . . . . 0.1(4) ?
    C24 C25 C26 C27 . . . . -0.4(3) ?
    C25 C26 C27 C22 . . . . 0.4(3) ?
    C25 C26 C27 S2 . . . . -179.52(16) no
    C23 C22 C27 C26 . . . . -0.2(3) ?
    C28 C22 C27 C26 . . . . 179.00(17) ?
    C23 C22 C27 S2 . . . . 179.75(15) no
    C28 C22 C27 S2 . . . . -1.1(2) no
    C23 C22 C28 C29 . . . . 180.00(19) ?
    C27 C22 C28 C29 . . . . 0.9(2) ?
    C23 C22 C28 N4 . . . . 3.1(3) ?
    C27 C22 C28 N4 . . . . -175.98(17) ?
    N4 C28 C29 C30 . . . . -4.6(3) ?
    C22 C28 C29 C30 . . . . 178.45(17) ?
    N4 C28 C29 S2 . . . . 176.55(14) no
    C22 C28 C29 S2 . . . . -0.4(2) no
    C28 C29 C30 O3 . . . . -176.1(2) ?
    S2 C29 C30 O3 . . . . 2.6(3) no
    C28 C29 C30 N5 . . . . 2.3(3) ?
    S2 C29 C30 N5 . . . . -179.03(13) no
    C37 C32 C33 C34 . . . . 2.7(3) ?
    N5 C32 C33 C34 . . . . -176.10(18) ?
    C32 C33 C34 C35 . . . . 0.1(3) ?
    C33 C34 C35 C36 . . . . -2.2(3) ?
    C33 C34 C35 C38 . . . . 179.2(2) ?
    C34 C35 C36 C37 . . . . 1.6(3) ?
    C38 C35 C36 C37 . . . . -179.8(2) ?
    C33 C32 C37 C36 . . . . -3.3(3) ?
    N5 C32 C37 C36 . . . . 175.52(18) ?
    C35 C36 C37 C32 . . . . 1.1(3) ?
    N6 C39 C40 O4 . . . . 58.2(2) ?
    N6 C41 C42 O4 . . . . -57.9(2) ?
    N3 C10 N1 C8 . . . . -177.33(15) ?
    N2 C10 N1 C8 . . . . -0.6(3) ?
    C7 C8 N1 C10 . . . . -0.1(3) ?
    C1 C8 N1 C10 . . . . -177.76(17) ?
    N1 C10 N2 C9 . . . . 0.3(3) ?
    N3 C10 N2 C9 . . . . 177.00(16) ?
    N1 C10 N2 C11 . . . . -176.05(17) ?
    N3 C10 N2 C11 . . . . 0.7(2) ?
    O1 C9 N2 C10 . . . . -177.84(19) ?
    C7 C9 N2 C10 . . . . 0.7(3) ?
    O1 C9 N2 C11 . . . . -1.3(3) ?
    C7 C9 N2 C11 . . . . 177.26(15) ?
    C16 C11 N2 C10 . . . . 58.9(2) ?
    C12 C11 N2 C10 . . . . -121.9(2) ?
    C16 C11 N2 C9 . . . . -117.6(2) ?
    C12 C11 N2 C9 . . . . 61.6(2) ?
    N1 C10 N3 C18 . . . . -116.9(2) ?
    N2 C10 N3 C18 . . . . 66.2(2) ?
    N1 C10 N3 C20 . . . . 18.1(2) ?
    N2 C10 N3 C20 . . . . -158.82(17) ?
    C19 C18 N3 C10 . . . . -166.84(17) ?
    C19 C18 N3 C20 . . . . 56.6(2) ?
    C21 C20 N3 C10 . . . . 162.57(19) ?
    C21 C20 N3 C18 . . . . -58.4(2) ?
    N6 C31 N4 C28 . . . . -179.87(15) ?
    N5 C31 N4 C28 . . . . 2.6(3) ?
    C29 C28 N4 C31 . . . . 2.1(3) ?
    C22 C28 N4 C31 . . . . 178.64(17) ?
    N4 C31 N5 C30 . . . . -4.9(3) ?
    N6 C31 N5 C30 . . . . 177.58(16) ?
    N4 C31 N5 C32 . . . . 168.88(17) ?
    N6 C31 N5 C32 . . . . -8.7(2) ?
    O3 C30 N5 C31 . . . . -179.35(18) ?
    C29 C30 N5 C31 . . . . 2.2(2) ?
    O3 C30 N5 C32 . . . . 6.6(3) ?
    C29 C30 N5 C32 . . . . -171.93(16) ?
    C37 C32 N5 C31 . . . . -57.7(2) ?
    C33 C32 N5 C31 . . . . 121.1(2) ?
    C37 C32 N5 C30 . . . . 116.43(19) ?
    C33 C32 N5 C30 . . . . -64.8(2) ?
    N4 C31 N6 C41 . . . . -9.9(2) ?
    N5 C31 N6 C41 . . . . 167.75(16) ?
    N4 C31 N6 C39 . . . . 123.90(19) ?
    N5 C31 N6 C39 . . . . -58.4(2) ?
    C42 C41 N6 C31 . . . . -165.60(17) ?
    C42 C41 N6 C39 . . . . 56.6(2) ?
    C40 C39 N6 C31 . . . . 166.54(17) ?
    C40 C39 N6 C41 . . . . -57.3(2) ?
    C18 C19 O2 C21 . . . . 57.3(3) ?
    C20 C21 O2 C19 . . . . -59.7(2) ?
    C39 C40 O4 C42 . . . . -58.3(2) ?
    C41 C42 O4 C40 . . . . 58.7(2) ?
    C8 C7 S1 C6 . . . . -0.71(16) no
    C9 C7 S1 C6 . . . . -179.54(18) no
    C5 C6 S1 C7 . . . . -179.53(18) no
    C1 C6 S1 C7 . . . . 1.01(15) no
    C28 C29 S2 C27 . . . . -0.19(15) no
    C30 C29 S2 C27 . . . . -178.99(18) no
    C26 C27 S2 C29 . . . . -179.34(19) no
    C22 C27 S2 C29 . . . . 0.72(15) no
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
    C17 H17C O1 3_757 0.96 2.58 3.304(3) 133
    C16 H16 O3 3_667 0.93 2.59 3.479(3) 160
    C4 H4 O2 4_566 0.93 2.57 3.395(3) 148
