#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/44/2224417.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2224417
loop_
_publ_author_name
'Wang, Hong-Mei'
'Xu, Jing'
'Zeng, Xiao-Hua'
'Tian, Jia-Hua'
_publ_section_title
;Ethyl
 2-(3,3-dibutylthioureido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate
;
_journal_coeditor_code           RZ2377
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3094
_journal_page_last               o3095
_journal_paper_doi               10.1107/S1600536809047230
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C20 H32 N2 O2 S2'
_chemical_formula_moiety         'C20 H32 N2 O2 S2'
_chemical_formula_sum            'C20 H32 N2 O2 S2'
_chemical_formula_weight         396.60
_chemical_name_systematic
;
Ethyl 2-(3,3-dibutylthioureido)-4,5,6,7-tetrahydrobenzo[b]thiophene-
3-carboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.711(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9311(11)
_cell_length_b                   21.715(3)
_cell_length_c                   9.6841(3)
_cell_measurement_reflns_used    9055
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      27.60
_cell_measurement_theta_min      2.17
_cell_volume                     2189.8(4)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12194
_diffrn_reflns_theta_full        25.5
_diffrn_reflns_theta_max         25.5
_diffrn_reflns_theta_min         2.1
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  0.9381
_exptl_absorpt_correction_T_min  0.9025
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.21
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4036
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.24
_refine_ls_R_factor_all          0.082
_refine_ls_R_factor_gt           0.073
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0275P)²+2.0031P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.149
_refine_ls_wR_factor_ref         0.153
_reflns_number_gt                3460
_reflns_number_total             4036
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2377.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2224417
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 1.0984(4) -0.00230(16) 0.7833(4) 0.0631(9) Uani d . 1 B .
C C2 1.1175(5) -0.0488(2) 0.9023(5) 0.0856(12) Uani d D 1 . .
H H2A 1.0446 -0.0765 0.8804 0.103 Uiso calc PR 0.71 A 1
H H2B 1.1237 -0.0280 0.9928 0.103 Uiso calc PR 0.71 A 1
H H2C 1.0714 -0.0361 0.9687 0.103 Uiso d PR 0.29 A 2
H H2D 1.0832 -0.0882 0.8616 0.103 Uiso d PR 0.29 A 2
C C3 1.2396(7) -0.0852(4) 0.9174(11) 0.097(2) Uani d PD 0.71 B 1
H H3A 1.2660 -0.1048 1.0119 0.117 Uiso calc PR 0.71 B 1
H H3B 1.2207 -0.1175 0.8448 0.117 Uiso calc PR 0.71 B 1
C C4 1.3461(8) -0.0488(4) 0.9018(8) 0.093(2) Uani d PD 0.71 B 1
H H4A 1.4202 -0.0754 0.9147 0.112 Uiso calc PR 0.71 B 1
H H4B 1.3686 -0.0177 0.9771 0.112 Uiso calc PR 0.71 B 1
C C4' 1.315(2) -0.0763(7) 0.8441(17) 0.077(5) Uani d PD 0.29 B 2
H H4'1 1.4018 -0.0918 0.8832 0.092 Uiso calc PR 0.29 B 2
H H4'2 1.2627 -0.1081 0.7835 0.092 Uiso calc PR 0.29 B 2
C C3' 1.2569(14) -0.0586(11) 0.9758(17) 0.113(9) Uani d PD 0.29 B 2
H H3'1 1.2705 -0.0918 1.0458 0.135 Uiso calc PR 0.29 B 2
H H3'2 1.2968 -0.0215 1.0251 0.135 Uiso calc PR 0.29 B 2
C C5 1.3142(4) -0.01737(18) 0.7532(4) 0.0751(10) Uani d D 1 . .
H H5A 1.3787 0.0136 0.7554 0.090 Uiso calc PR 0.71 B 1
H H5B 1.3163 -0.0476 0.6803 0.090 Uiso calc PR 0.71 B 1
H H5C 1.3789 0.0116 0.8067 0.090 Uiso d PR 0.29 B 2
H H5D 1.3339 -0.0286 0.6653 0.090 Uiso d PR 0.29 B 2
C C6 1.1838(3) 0.01239(15) 0.7127(3) 0.0577(8) Uani d . 1 B .
C C7 1.1347(3) 0.05951(15) 0.6064(3) 0.0551(8) Uani d . 1 . .
C C8 1.0133(3) 0.07897(14) 0.6033(3) 0.0542(7) Uani d . 1 B .
C C9 1.1975(3) 0.08581(17) 0.5067(4) 0.0634(9) Uani d . 1 B .
C C10 1.3820(4) 0.0835(2) 0.4231(5) 0.0951(14) Uani d . 1 B .
H H10A 1.3581 0.1259 0.3967 0.114 Uiso calc R 1 . .
H H10B 1.4735 0.0824 0.4730 0.114 Uiso calc R 1 . .
C C11 1.3540(5) 0.0462(2) 0.2931(5) 0.1069(16) Uani d . 1 . .
H H11A 1.3741 0.0040 0.3193 0.160 Uiso calc R 1 . .
H H11B 1.4048 0.0602 0.2340 0.160 Uiso calc R 1 . .
H H11C 1.2646 0.0498 0.2398 0.160 Uiso calc R 1 . .
C C12 0.8369(3) 0.15459(17) 0.5066(4) 0.0659(9) Uani d . 1 B .
C C13 0.6951(5) 0.2433(2) 0.4072(6) 0.1029(15) Uani d D 1 B .
H H13A 0.6756 0.2414 0.4983 0.123 Uiso calc R 1 . .
H H13B 0.7147 0.2858 0.3911 0.123 Uiso calc R 1 . .
C C14 0.5827(5) 0.2238(3) 0.2904(6) 0.1242(19) Uani d D 1 . .
H H14A 0.5686 0.1800 0.2980 0.149 Uiso calc PR 0.83 C 1
H H14B 0.5957 0.2317 0.1973 0.149 Uiso calc PR 0.83 C 1
H H14C 0.5373 0.1905 0.3203 0.149 Uiso d PR 0.17 C 2
H H14D 0.6066 0.2106 0.2064 0.149 Uiso d PR 0.17 C 2
C C15 0.4615(9) 0.2616(5) 0.3037(12) 0.181(5) Uani d PD 0.83 D 1
H H15A 0.3847 0.2396 0.2496 0.217 Uiso calc PR 0.83 D 1
H H15B 0.4641 0.2612 0.4047 0.217 Uiso calc PR 0.83 D 1
C C16 0.4496(12) 0.3174(5) 0.2607(16) 0.232(7) Uani d PD 0.83 D 1
H H16A 0.5305 0.3381 0.2977 0.348 Uiso calc PR 0.83 D 1
H H16B 0.3864 0.3376 0.2953 0.348 Uiso calc PR 0.83 D 1
H H16C 0.4228 0.3184 0.1567 0.348 Uiso calc PR 0.83 D 1
C C15' 0.4923(18) 0.2749(12) 0.213(3) 0.090(8) Uani d PD 0.17 D 2
H H15C 0.5365 0.3140 0.2372 0.108 Uiso calc PR 0.17 D 2
H H15D 0.4727 0.2690 0.1094 0.108 Uiso calc PR 0.17 D 2
C C16' 0.372(2) 0.2782(14) 0.248(5) 0.125(13) Uani d PD 0.17 D 2
H H16D 0.3180 0.3090 0.1892 0.188 Uiso calc PR 0.17 D 2
H H16E 0.3897 0.2888 0.3487 0.188 Uiso calc PR 0.17 D 2
H H16F 0.3298 0.2390 0.2303 0.188 Uiso calc PR 0.17 D 2
C C17 0.9008(4) 0.23002(19) 0.3483(5) 0.0814(11) Uani d . 1 B .
H H17A 0.8536 0.2535 0.2637 0.098 Uiso calc R 1 . .
H H17B 0.9449 0.1968 0.3162 0.098 Uiso calc R 1 . .
C C18 0.9998(4) 0.2719(2) 0.4523(5) 0.0897(13) Uani d . 1 . .
H H18A 0.9553 0.3058 0.4813 0.108 Uiso calc R 1 . .
H H18B 1.0437 0.2487 0.5388 0.108 Uiso calc R 1 . .
C C19 1.0961(5) 0.2970(2) 0.3882(5) 0.1017(15) Uani d . 1 . .
H H19A 1.0523 0.3158 0.2955 0.122 Uiso calc R 1 . .
H H19B 1.1485 0.2635 0.3709 0.122 Uiso calc R 1 . .
C C20 1.1828(5) 0.3447(2) 0.4862(6) 0.126(2) Uani d . 1 . .
H H20A 1.1321 0.3792 0.4981 0.190 Uiso calc R 1 . .
H H20B 1.2465 0.3582 0.4432 0.190 Uiso calc R 1 . .
H H20C 1.2244 0.3266 0.5791 0.190 Uiso calc R 1 . .
N N1 0.9493(3) 0.12572(14) 0.5138(3) 0.0637(7) Uani d D 1 . .
H H1A 0.997(3) 0.1387(16) 0.464(3) 0.076 Uiso d D 1 . .
N N2 0.8108(3) 0.20414(16) 0.4177(4) 0.0801(9) Uani d . 1 . .
O O1 1.3122(2) 0.06116(13) 0.5196(3) 0.0769(7) Uani d . 1 . .
O O2 1.1519(3) 0.12628(13) 0.4189(3) 0.0869(8) Uani d . 1 . .
S S1 0.95706(9) 0.03954(4) 0.72506(10) 0.0662(3) Uani d . 1 . .
S S2 0.74212(10) 0.13005(5) 0.60210(13) 0.0823(3) Uani d . 1 . .
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'
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
C6 C1 C2 . . 126.3(4) ?
C6 C1 S1 . . 113.3(3) ?
C2 C1 S1 . . 120.4(3) ?
C3' C2 C1 . . 110.3(8) ?
C1 C2 C3 . . 109.7(4) ?
C3' C2 H2A . . 132.0 ?
C1 C2 H2A . . 109.7 ?
C3 C2 H2A . . 109.7 ?
C3' C2 H2B . . 81.6 ?
C1 C2 H2B . . 109.7 ?
C3 C2 H2B . . 109.7 ?
H2A C2 H2B . . 108.2 ?
C3' C2 H2C . . 112.7 ?
C1 C2 H2C . . 109.8 ?
C3 C2 H2C . . 134.6 ?
H2A C2 H2C . . 76.3 ?
C3' C2 H2D . . 106.3 ?
C1 C2 H2D . . 109.6 ?
C3 C2 H2D . . 78.4 ?
H2B C2 H2D . . 133.7 ?
H2C C2 H2D . . 107.8 ?
C4 C3 C2 . . 114.6(6) ?
C4 C3 H3A . . 108.6 ?
C2 C3 H3A . . 108.6 ?
C4 C3 H3B . . 108.6 ?
C2 C3 H3B . . 108.6 ?
H3A C3 H3B . . 107.6 ?
C3 C4 C5 . . 112.3(7) ?
C3 C4 H4A . . 109.2 ?
C5 C4 H4A . . 109.2 ?
C3 C4 H4B . . 109.2 ?
C5 C4 H4B . . 109.2 ?
H4A C4 H4B . . 107.9 ?
C5 C4' C3' . . 108.2(12) ?
C5 C4' H4'1 . . 110.1 ?
C3' C4' H4'1 . . 110.1 ?
C5 C4' H4'2 . . 110.1 ?
C3' C4' H4'2 . . 110.1 ?
H4'1 C4' H4'2 . . 108.4 ?
C2 C3' C4' . . 104.1(12) ?
C2 C3' H3'1 . . 110.9 ?
C4' C3' H3'1 . . 110.9 ?
C2 C3' H3'2 . . 110.9 ?
C4' C3' H3'2 . . 110.9 ?
H3'1 C3' H3'2 . . 109.0 ?
C6 C5 C4 . . 111.3(4) ?
C6 C5 C4' . . 110.0(8) ?
C6 C5 H5A . . 109.4 ?
C4 C5 H5A . . 109.4 ?
C4' C5 H5A . . 133.0 ?
C6 C5 H5B . . 109.4 ?
C4 C5 H5B . . 109.4 ?
H5A C5 H5B . . 108.0 ?
C6 C5 H5C . . 109.9 ?
C4' C5 H5C . . 110.8 ?
H5B C5 H5C . . 130.8 ?
C6 C5 H5D . . 108.9 ?
C4 C5 H5D . . 131.5 ?
C4' C5 H5D . . 109.0 ?
H5C C5 H5D . . 108.1 ?
C1 C6 C7 . . 111.5(3) ?
C1 C6 C5 . . 120.8(3) ?
C7 C6 C5 . . 127.6(3) ?
C8 C7 C6 . . 112.3(3) ?
C8 C7 C9 . . 120.4(3) ?
C6 C7 C9 . . 127.2(3) ?
N1 C8 C7 . . 122.5(3) ?
N1 C8 S1 . . 125.5(2) ?
C7 C8 S1 . . 112.0(2) ?
O2 C9 O1 . . 121.9(3) ?
O2 C9 C7 . . 124.6(3) ?
O1 C9 C7 . . 113.5(3) ?
C11 C10 O1 . . 111.0(4) ?
C11 C10 H10A . . 109.4 ?
O1 C10 H10A . . 109.4 ?
C11 C10 H10B . . 109.4 ?
O1 C10 H10B . . 109.4 ?
H10A C10 H10B . . 108.0 ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
N2 C12 N1 . . 114.3(3) ?
N2 C12 S2 . . 124.0(3) ?
N1 C12 S2 . . 121.7(3) ?
C14 C13 N2 . . 112.5(4) ?
C14 C13 H13A . . 109.1 ?
N2 C13 H13A . . 109.1 ?
C14 C13 H13B . . 109.1 ?
N2 C13 H13B . . 109.1 ?
H13A C13 H13B . . 107.8 ?
C13 C14 C15' . . 116.0(11) ?
C13 C14 C15 . . 108.2(6) ?
C13 C14 H14A . . 110.1 ?
C15' C14 H14A . . 131.1 ?
C15 C14 H14A . . 110.1 ?
C13 C14 H14B . . 110.1 ?
C15 C14 H14B . . 110.1 ?
H14A C14 H14B . . 108.4 ?
C13 C14 H14C . . 111.9 ?
C15' C14 H14C . . 112.0 ?
H14B C14 H14C . . 130.0 ?
C13 C14 H14D . . 111.0 ?
C15' C14 H14D . . 95.9 ?
C15 C14 H14D . . 131.3 ?
H14C C14 H14D . . 108.9 ?
C16 C15 C14 . . 117.9(11) ?
C16 C15 H15A . . 107.8 ?
C14 C15 H15A . . 107.8 ?
C16 C15 H15B . . 107.8 ?
C14 C15 H15B . . 107.8 ?
H15A C15 H15B . . 107.2 ?
C16' C15' C14 . . 114.7(19) ?
C16' C15' H15C . . 108.6 ?
C14 C15' H15C . . 108.6 ?
C16' C15' H15D . . 108.6 ?
C14 C15' H15D . . 108.6 ?
H15C C15' H15D . . 107.6 ?
C15' C16' H16D . . 109.5 ?
C15' C16' H16E . . 109.5 ?
H16D C16' H16E . . 109.5 ?
C15' C16' H16F . . 109.5 ?
H16D C16' H16F . . 109.5 ?
H16E C16' H16F . . 109.5 ?
N2 C17 C18 . . 111.4(4) ?
N2 C17 H17A . . 109.3 ?
C18 C17 H17A . . 109.3 ?
N2 C17 H17B . . 109.3 ?
C18 C17 H17B . . 109.3 ?
H17A C17 H17B . . 108.0 ?
C19 C18 C17 . . 113.1(4) ?
C19 C18 H18A . . 108.9 ?
C17 C18 H18A . . 108.9 ?
C19 C18 H18B . . 108.9 ?
C17 C18 H18B . . 109.0 ?
H18A C18 H18B . . 107.8 ?
C18 C19 C20 . . 112.1(4) ?
C18 C19 H19A . . 109.2 ?
C20 C19 H19A . . 109.2 ?
C18 C19 H19B . . 109.2 ?
C20 C19 H19B . . 109.2 ?
H19A C19 H19B . . 107.9 ?
C19 C20 H20A . . 109.5 ?
C19 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C19 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C12 N1 C8 . . 130.4(3) ?
C12 N1 H1A . . 121(3) ?
C8 N1 H1A . . 109(3) ?
C12 N2 C17 . . 123.9(3) ?
C12 N2 C13 . . 120.2(4) ?
C17 N2 C13 . . 114.9(3) ?
C9 O1 C10 . . 117.8(3) ?
C8 S1 C1 . . 90.86(16) ?
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 C6 . 1.352(4) ?
C1 C2 . 1.498(5) ?
C1 S1 . 1.732(4) ?
C2 C3' . 1.488(15) ?
C2 C3 . 1.520(8) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C2 H2C . 0.9700 ?
C2 H2D . 0.9700 ?
C3 C4 . 1.452(11) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C5 . 1.534(7) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C4' C5 . 1.552(14) ?
C4' C3' . 1.63(2) ?
C4' H4'1 . 0.9700 ?
C4' H4'2 . 0.9700 ?
C3' H3'1 . 0.9700 ?
C3' H3'2 . 0.9700 ?
C5 C6 . 1.505(5) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C5 H5C . 0.9700 ?
C5 H5D . 0.9700 ?
C6 C7 . 1.435(4) ?
C7 C8 . 1.385(4) ?
C7 C9 . 1.460(4) ?
C8 N1 . 1.380(4) ?
C8 S1 . 1.715(3) ?
C9 O2 . 1.219(4) ?
C9 O1 . 1.333(4) ?
C10 C11 . 1.449(6) ?
C10 O1 . 1.458(4) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 N2 . 1.353(5) ?
C12 N1 . 1.362(4) ?
C12 S2 . 1.672(4) ?
C13 C14 . 1.457(6) ?
C13 N2 . 1.502(5) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C15' . 1.522(16) ?
C14 C15 . 1.597(9) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C14 H14C . 0.9700 ?
C14 H14D . 0.9700 ?
C15 C16 . 1.274(11) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C15' C16' . 1.454(19) ?
C15' H15C . 0.9700 ?
C15' H15D . 0.9700 ?
C16' H16D . 0.9600 ?
C16' H16E . 0.9600 ?
C16' H16F . 0.9600 ?
C17 N2 . 1.461(5) ?
C17 C18 . 1.532(6) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C18 C19 . 1.480(6) ?
C18 H18A . 0.9700 ?
C18 H18B . 0.9700 ?
C19 C20 . 1.524(6) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 0.9600 ?
N1 H1A . 0.86(3) ?
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
N1 H1A O2 . 0.86(3) 1.89(2) 2.643(4) 145(3) y
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' . . . . 23.4(10) ?
S1 C1 C2 C3' . . . . -155.7(8) ?
C6 C1 C2 C3 . . . . -9.1(7) ?
S1 C1 C2 C3 . . . . 171.9(5) ?
C3' C2 C3 C4 . . . . -57.1(15) ?
C1 C2 C3 C4 . . . . 39.8(10) ?
C2 C3 C4 C5 . . . . -59.9(11) ?
C1 C2 C3' C4' . . . . -54.3(15) ?
C3 C2 C3' C4' . . . . 40.2(10) ?
C5 C4' C3' C2 . . . . 71.5(17) ?
C3 C4 C5 C6 . . . . 45.6(9) ?
C3 C4 C5 C4' . . . . -48.1(16) ?
C3' C4' C5 C6 . . . . -50.6(14) ?
C3' C4' C5 C4 . . . . 47.6(13) ?
C2 C1 C6 C7 . . . . -179.1(4) ?
S1 C1 C6 C7 . . . . 0.0(4) ?
C2 C1 C6 C5 . . . . -1.7(6) ?
S1 C1 C6 C5 . . . . 177.4(3) ?
C4 C5 C6 C1 . . . . -15.9(6) ?
C4' C5 C6 C1 . . . . 17.0(8) ?
C4 C5 C6 C7 . . . . 161.0(5) ?
C4' C5 C6 C7 . . . . -166.1(7) ?
C1 C6 C7 C8 . . . . 0.8(4) ?
C5 C6 C7 C8 . . . . -176.3(3) ?
C1 C6 C7 C9 . . . . -178.1(3) ?
C5 C6 C7 C9 . . . . 4.8(6) ?
C6 C7 C8 N1 . . . . 177.3(3) ?
C9 C7 C8 N1 . . . . -3.7(5) ?
C6 C7 C8 S1 . . . . -1.3(4) ?
C9 C7 C8 S1 . . . . 177.7(3) ?
C8 C7 C9 O2 . . . . 1.8(6) ?
C6 C7 C9 O2 . . . . -179.4(4) ?
C8 C7 C9 O1 . . . . -178.1(3) ?
C6 C7 C9 O1 . . . . 0.8(5) ?
N2 C13 C14 C15' . . . . -145.7(11) ?
N2 C13 C14 C15 . . . . 171.8(5) ?
C13 C14 C15 C16 . . . . 76.9(14) ?
C15' C14 C15 C16 . . . . -32.1(19) ?
C13 C14 C15' C16' . . . . -106(3) ?
C15 C14 C15' C16' . . . . -19(2) ?
N2 C17 C18 C19 . . . . 177.6(4) ?
C17 C18 C19 C20 . . . . 172.7(4) ?
N2 C12 N1 C8 . . . . 171.8(3) ?
S2 C12 N1 C8 . . . . -7.6(5) ?
C7 C8 N1 C12 . . . . -172.7(3) ?
S1 C8 N1 C12 . . . . 5.7(5) ?
N1 C12 N2 C17 . . . . -7.3(5) ?
S2 C12 N2 C17 . . . . 172.2(3) ?
N1 C12 N2 C13 . . . . -175.5(3) ?
S2 C12 N2 C13 . . . . 3.9(5) ?
C18 C17 N2 C12 . . . . -81.1(5) ?
C18 C17 N2 C13 . . . . 87.7(4) ?
C14 C13 N2 C12 . . . . -92.5(5) ?
C14 C13 N2 C17 . . . . 98.3(5) ?
O2 C9 O1 C10 . . . . -0.9(6) ?
C7 C9 O1 C10 . . . . 178.9(3) ?
C11 C10 O1 C9 . . . . -92.2(5) ?
N1 C8 S1 C1 . . . . -177.4(3) ?
C7 C8 S1 C1 . . . . 1.1(3) ?
C6 C1 S1 C8 . . . . -0.7(3) ?
C2 C1 S1 C8 . . . . 178.5(3) ?
