#------------------------------------------------------------------------------
#$Date: 2025-08-19 08:12:48 +0200 (Tue, 19 Aug 2025) $
#$Revision: 301798 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/2/01/54/2015439.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_2015439
loop_
_publ_author_name
'Hartung, Jens'
'Schwarz, Michaela'
'Paulus, Erich F.'
'Svoboda, Ingrid'
'Fuess, Hartmut'
_publ_section_title
4-(4-Chlorophenyl)-3-(4-phenylpent-4-enyloxy)-1,3-thiazole-2(3H)-thione
_journal_coeditor_code           HJ1090
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o386
_journal_page_last               o388
_journal_paper_doi               10.1107/S0108270106004677
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C20 H18 Cl N O S2'
_chemical_formula_moiety         'C20 H18 Cl N O S2'
_chemical_formula_sum            'C20 H18 Cl N O S2'
_chemical_formula_weight         387.92
_chemical_name_systematic
;
4-(4-Chlorophenyl)-3-(4-phenylpent-4-enyloxy)thiazole-2(3H)-thione
;
_space_group_IT_number           159
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 3 -2c'
_symmetry_space_group_name_H-M   'P 3 1 c'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   36.21710(10)
_cell_length_b                   36.21710(10)
_cell_length_c                   7.66950(10)
_cell_measurement_reflns_used    10106
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.73
_cell_measurement_theta_min      1.12
_cell_volume                     8712.14(12)
_computing_cell_refinement       AXS-software
_computing_data_collection       AXS-software
_computing_data_reduction        AXS-software
_computing_molecular_graphics
'PLATON (Spek, 2003) and ORTEP-3 (Farrugia, 1997, 2005)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.944
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'Bruker four-circle CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode,focus:0.5 x 5mm,50 kV,120 mA'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            49608
_diffrn_reflns_theta_full        25.73
_diffrn_reflns_theta_max         25.73
_diffrn_reflns_theta_min         1.30
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.421
_exptl_absorpt_correction_T_max  0.9206
_exptl_absorpt_correction_T_min  0.8236
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'hexagonal rod'
_exptl_crystal_F_000             3636
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.155
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.11(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.296
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     677
_refine_ls_number_reflns         10106
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.296
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0487
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0132P)²+4.1632P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0964
_reflns_number_gt                8858
_reflns_number_total             10106
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hj1090.cif
_cod_data_source_block           I
_cod_database_code               2015439
_cod_database_fobs_code          2015439
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, z+1/2'
'x-y, -y, z+1/2'
'-x, -x+y, 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
O O11 0.27828(10) 0.48772(8) 0.1173(4) 0.0551(8) Uani d . 1
C C102 0.31916(19) 0.56186(14) 0.0614(8) 0.0761(16) Uani d . 1
N N13 0.28050(12) 0.52631(11) 0.0815(6) 0.0615(10) Uani d . 1
C C104 0.24403(17) 0.52983(16) 0.0679(8) 0.0688(14) Uani d . 1
C C105 0.2548(2) 0.57056(19) 0.0332(10) 0.093(2) Uani d . 1
H H105 0.2352 0.5798 0.0180 0.140 Uiso calc R 1
C C106 0.20030(17) 0.49291(16) 0.0833(7) 0.0638(13) Uani d . 1
C C107 0.1681(2) 0.4907(2) -0.0230(8) 0.0832(17) Uani d . 1
H H107 0.1746 0.5118 -0.1062 0.125 Uiso calc R 1
C C108 0.1270(2) 0.4582(2) -0.0069(9) 0.093(2) Uani d . 1
H H108 0.1057 0.4579 -0.0758 0.139 Uiso calc R 1
C C109 0.11706(18) 0.4261(2) 0.1095(9) 0.0812(17) Uani d . 1
C C110 0.14750(18) 0.42635(17) 0.2179(8) 0.0726(15) Uani d . 1
H H110 0.1405 0.4045 0.2976 0.109 Uiso calc R 1
C C111 0.18944(17) 0.46060(16) 0.2043(7) 0.0641(13) Uani d . 1
H H111 0.2103 0.4616 0.2780 0.096 Uiso calc R 1
C C112 0.28060(16) 0.46836(13) -0.0469(7) 0.0603(13) Uani d . 1
H H11 0.3076 0.4864 -0.1046 0.090 Uiso calc R 1
H H12 0.2577 0.4644 -0.1245 0.090 Uiso calc R 1
C C113 0.27633(15) 0.42587(14) -0.0005(7) 0.0639(13) Uani d . 1
H H13 0.2841 0.4151 -0.1012 0.096 Uiso calc R 1
H H14 0.2963 0.4302 0.0922 0.096 Uiso calc R 1
C C114 0.23302(16) 0.39344(14) 0.0564(7) 0.0648(13) Uani d . 1
H H15 0.2129 0.3919 -0.0310 0.097 Uiso calc R 1
H H16 0.2267 0.4034 0.1635 0.097 Uiso calc R 1
C C115 0.22496(16) 0.34864(15) 0.0875(8) 0.0681(14) Uani d . 1
C C116 0.2545(2) 0.33901(19) 0.0636(14) 0.128(3) Uani d . 1
H H17 0.2486 0.3111 0.0794 0.192 Uiso calc R 1
H H18 0.2818 0.3600 0.0306 0.192 Uiso calc R 1
C C117 0.18099(17) 0.31590(14) 0.1404(7) 0.0644(13) Uani d . 1
C C118 0.14614(16) 0.32236(16) 0.1206(8) 0.0727(15) Uani d . 1
H H118 0.1505 0.3478 0.0726 0.109 Uiso calc R 1
C C119 0.10576(18) 0.29202(18) 0.1704(8) 0.0850(18) Uani d . 1
H H119 0.0832 0.2971 0.1541 0.128 Uiso calc R 1
C C120 0.0982(2) 0.25426(19) 0.2442(9) 0.0899(19) Uani d . 1
H H120 0.0708 0.2338 0.2782 0.135 Uiso calc R 1
C C121 0.1315(2) 0.24736(17) 0.2663(8) 0.0849(17) Uani d . 1
H H121 0.1267 0.2218 0.3151 0.127 Uiso calc R 1
C C122 0.17240(18) 0.27757(15) 0.2176(8) 0.0740(15) Uani d . 1
H H122 0.1947 0.2722 0.2368 0.111 Uiso calc R 1
Cl Cl1 0.06499(6) 0.38341(7) 0.1270(3) 0.1278(7) Uani d . 1
S S11 0.30874(6) 0.60296(5) 0.0208(3) 0.1043(6) Uani d . 1
S S12 0.36709(4) 0.56718(4) 0.0708(3) 0.0807(4) Uani d . 1
O O21 0.17492(9) 0.03906(9) 0.1929(4) 0.0543(8) Uani d . 1
C C202 0.10099(15) 0.00329(18) 0.2575(9) 0.0712(15) Uani d . 1
N N23 0.13806(11) 0.03959(11) 0.2392(6) 0.0616(11) Uani d . 1
C C204 0.13751(15) 0.07788(15) 0.2394(8) 0.0643(13) Uani d . 1
C C205 0.09797(15) 0.07055(17) 0.2667(9) 0.0810(18) Uani d . 1
H H205 0.0907 0.0918 0.2717 0.121 Uiso calc R 1
C C206 0.17553(14) 0.11999(14) 0.2057(7) 0.0545(12) Uani d . 1
C C207 0.17110(17) 0.14783(16) 0.0922(8) 0.0754(15) Uani d . 1
H H207 0.1451 0.1391 0.0376 0.113 Uiso calc R 1
C C208 0.20520(19) 0.18819(18) 0.0609(9) 0.0856(17) Uani d . 1
H H208 0.2022 0.2070 -0.0121 0.128 Uiso calc R 1
C C209 0.24329(17) 0.19978(15) 0.1393(8) 0.0700(15) Uani d . 1
C C210 0.24897(15) 0.17351(15) 0.2498(8) 0.0656(14) Uani d . 1
H H210 0.2754 0.1822 0.3008 0.098 Uiso calc R 1
C C211 0.21426(15) 0.13353(14) 0.2840(7) 0.0605(13) Uani d . 1
H H211 0.2173 0.1155 0.3617 0.091 Uiso calc R 1
C C212 0.19260(14) 0.02767(16) 0.3404(7) 0.0609(13) Uani d . 1
H H22 0.1724 -0.0006 0.3827 0.091 Uiso calc R 1
H H21 0.1996 0.0479 0.4349 0.091 Uiso calc R 1
C C213 0.23238(14) 0.02887(15) 0.2722(7) 0.0639(13) Uani d . 1
H H24 0.2248 0.0097 0.1733 0.096 Uiso calc R 1
H H23 0.2438 0.0186 0.3623 0.096 Uiso calc R 1
C C214 0.26671(14) 0.07332(16) 0.2164(7) 0.0647(13) Uani d . 1
H H25 0.2560 0.0820 0.1182 0.097 Uiso calc R 1
H H26 0.2715 0.0929 0.3114 0.097 Uiso calc R 1
C C215 0.30922(15) 0.07799(18) 0.1652(8) 0.0688(15) Uani d . 1
C C216 0.31574(19) 0.0465(2) 0.1418(11) 0.117(3) Uani d . 1
H H27 0.3426 0.0515 0.1087 0.175 Uiso calc R 1
H H28 0.2936 0.0187 0.1580 0.175 Uiso calc R 1
C C217 0.34425(15) 0.12313(18) 0.1402(7) 0.0673(14) Uani d . 1
C C218 0.33627(15) 0.15501(17) 0.0854(8) 0.0703(14) Uani d . 1
H H218 0.3082 0.1482 0.0663 0.106 Uiso calc R 1
C C219 0.36856(17) 0.19663(19) 0.0581(8) 0.0792(16) Uani d . 1
H H219 0.3623 0.2171 0.0176 0.119 Uiso calc R 1
C C220 0.40976(18) 0.2071(2) 0.0918(8) 0.0837(17) Uani d . 1
H H220 0.4317 0.2350 0.0754 0.126 Uiso calc R 1
C C221 0.41892(16) 0.1772(2) 0.1488(8) 0.0804(18) Uani d . 1
H H221 0.4471 0.1848 0.1702 0.121 Uiso calc R 1
C C222 0.38689(16) 0.1353(2) 0.1757(7) 0.0798(17) Uani d . 1
H H222 0.3937 0.1154 0.2174 0.120 Uiso calc R 1
Cl Cl2 0.28707(6) 0.25040(5) 0.0946(3) 0.1127(6) Uani d . 1
S S21 0.06202(4) 0.01696(5) 0.2915(3) 0.0990(6) Uani d . 1
S S22 0.09101(4) -0.04685(4) 0.2431(3) 0.0856(5) Uani d . 1
O O31 -0.16453(9) 0.48097(8) 0.1152(4) 0.0525(7) Uani d . 1
C C302 -0.23863(15) 0.43639(14) 0.0580(8) 0.0695(15) Uani d . 1
N N33 -0.19908(11) 0.44128(10) 0.0762(6) 0.0564(9) Uani d . 1
C C304 -0.19395(16) 0.40566(14) 0.0569(8) 0.0663(13) Uani d . 1
C C305 -0.23231(19) 0.37109(16) 0.0240(9) 0.089(2) Uani d . 1
H H305 -0.2363 0.3439 0.0078 0.133 Uiso calc R 1
C C306 -0.15241(15) 0.40760(13) 0.0706(7) 0.0624(13) Uani d . 1
C C307 -0.1427(2) 0.38534(18) -0.0510(9) 0.0870(18) Uani d . 1
H H307 -0.1614 0.3708 -0.1417 0.131 Uiso calc R 1
C C308 -0.1048(2) 0.3850(2) -0.0356(10) 0.104(2) Uani d . 1
H H308 -0.0977 0.3707 -0.1181 0.156 Uiso calc R 1
C C309 -0.07788(18) 0.40542(18) 0.1000(10) 0.0794(16) Uani d . 1
C C310 -0.08697(18) 0.42726(15) 0.2214(8) 0.0704(15) Uani d . 1
H H310 -0.0683 0.4410 0.3133 0.106 Uiso calc R 1
C C311 -0.12427(16) 0.42859(14) 0.2060(7) 0.0645(13) Uani d . 1
H H311 -0.1306 0.4437 0.2872 0.097 Uiso calc R 1
C C312 -0.14780(14) 0.50642(14) -0.0449(6) 0.0572(12) Uani d . 1
H H31 -0.1690 0.5120 -0.0964 0.086 Uiso calc R 1
H H32 -0.1402 0.4914 -0.1295 0.086 Uiso calc R 1
C C313 -0.10886(13) 0.54758(14) 0.0085(7) 0.0586(12) Uani d . 1
H H34 -0.1162 0.5599 0.1057 0.088 Uiso calc R 1
H H33 -0.1000 0.5676 -0.0879 0.088 Uiso calc R 1
C C314 -0.07197(13) 0.54130(13) 0.0608(7) 0.0556(12) Uani d . 1
H H35 -0.0677 0.5254 -0.0308 0.083 Uiso calc R 1
H H36 -0.0801 0.5239 0.1653 0.083 Uiso calc R 1
C C315 -0.02942(14) 0.58185(14) 0.0955(8) 0.0631(12) Uani d . 1
C C316 -0.02578(17) 0.61901(16) 0.1074(10) 0.094(2) Uani d . 1
H H38 0.0009 0.6429 0.1258 0.140 Uiso calc R 1
H H37 -0.0498 0.6219 0.0976 0.140 Uiso calc R 1
C C317 0.00791(13) 0.57527(13) 0.1102(7) 0.0538(11) Uani d . 1
C C318 0.00397(17) 0.53796(17) 0.1770(8) 0.0698(14) Uani d . 1
H H318 -0.0226 0.5167 0.2161 0.105 Uiso calc R 1
C C319 0.03825(18) 0.53138(19) 0.1873(8) 0.0831(17) Uani d . 1
H H319 0.0347 0.5059 0.2316 0.125 Uiso calc R 1
C C320 0.07765(17) 0.56258(19) 0.1319(7) 0.0740(16) Uani d . 1
H H320 0.1009 0.5583 0.1395 0.111 Uiso calc R 1
C C321 0.08295(15) 0.59997(18) 0.0656(7) 0.0712(15) Uani d . 1
H H321 0.1097 0.6211 0.0285 0.107 Uiso calc R 1
C C322 0.04824(14) 0.60632(16) 0.0537(7) 0.0645(13) Uani d . 1
H H322 0.0520 0.6317 0.0073 0.097 Uiso calc R 1
Cl Cl3 -0.03108(6) 0.40294(7) 0.1203(3) 0.1279(7) Uani d . 1
S S31 -0.27244(5) 0.38239(4) 0.0154(3) 0.0995(6) Uani d . 1
S S32 -0.25399(4) 0.47203(4) 0.0733(2) 0.0758(4) 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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
N13 O11 C112 108.9(3) ?
N13 C102 S12 129.2(3) ?
N13 C102 S11 105.7(4) yes
S12 C102 S11 125.1(3) ?
C102 N13 O11 119.4(4) ?
C102 N13 C104 118.7(4) yes
O11 N13 C104 121.8(4) ?
C105 C104 N13 110.2(5) yes
C105 C104 C106 126.6(5) ?
N13 C104 C106 123.1(4) ?
C104 C105 S11 111.6(4) yes
C104 C105 H105 124.2 ?
S11 C105 H105 124.2 ?
C111 C106 C107 117.9(5) ?
C111 C106 C104 122.6(5) ?
C107 C106 C104 119.5(5) ?
C108 C107 C106 121.1(6) ?
C108 C107 H107 119.5 ?
C106 C107 H107 119.5 ?
C109 C108 C107 120.4(6) ?
C109 C108 H108 119.8 ?
C107 C108 H108 119.8 ?
C108 C109 C110 121.4(6) ?
C108 C109 Cl1 120.9(5) ?
C110 C109 Cl1 117.7(5) ?
C109 C110 C111 118.0(5) ?
C109 C110 H110 121.0 ?
C111 C110 H110 121.0 ?
C106 C111 C110 121.3(5) ?
C106 C111 H111 119.4 ?
C110 C111 H111 119.4 ?
O11 C112 C113 106.5(4) ?
O11 C112 H11 110.4 ?
C113 C112 H11 110.4 ?
O11 C112 H12 110.4 ?
C113 C112 H12 110.4 ?
H11 C112 H12 108.6 ?
C114 C113 C112 114.0(4) ?
C114 C113 H13 108.8 ?
C112 C113 H13 108.8 ?
C114 C113 H14 108.8 ?
C112 C113 H14 108.8 ?
H13 C113 H14 107.7 ?
C113 C114 C115 117.2(4) ?
C113 C114 H15 108.0 ?
C115 C114 H15 108.0 ?
C113 C114 H16 108.0 ?
C115 C114 H16 108.0 ?
H15 C114 H16 107.3 ?
C116 C115 C117 121.6(5) ?
C116 C115 C114 121.5(5) ?
C117 C115 C114 116.9(4) ?
C115 C116 H17 120.0 ?
C115 C116 H18 120.0 ?
H17 C116 H18 120.0 ?
C122 C117 C118 116.1(5) ?
C122 C117 C115 121.7(5) ?
C118 C117 C115 122.1(4) ?
C119 C118 C117 121.6(5) ?
C119 C118 H118 119.2 ?
C117 C118 H118 119.2 ?
C118 C119 C120 120.9(6) ?
C118 C119 H119 119.6 ?
C120 C119 H119 119.6 ?
C121 C120 C119 118.7(6) ?
C121 C120 H120 120.6 ?
C119 C120 H120 120.6 ?
C120 C121 C122 121.3(6) ?
C120 C121 H121 119.4 ?
C122 C121 H121 119.4 ?
C121 C122 C117 121.4(6) ?
C121 C122 H122 119.3 ?
C117 C122 H122 119.3 ?
C105 S11 C102 93.7(3) yes
N23 O21 C212 111.5(3) ?
N23 C202 S22 128.9(4) ?
N23 C202 S21 107.2(4) yes
S22 C202 S21 123.8(3) ?
C202 N23 O21 120.8(3) ?
C202 N23 C204 118.1(4) yes
O21 N23 C204 120.3(3) ?
C205 C204 N23 110.4(4) yes
C205 C204 C206 125.8(5) ?
N23 C204 C206 123.7(4) ?
C204 C205 S21 111.8(4) yes
C204 C205 H205 124.1 ?
S21 C205 H205 124.1 ?
C211 C206 C207 118.7(4) ?
C211 C206 C204 123.4(4) ?
C207 C206 C204 117.9(4) ?
C208 C207 C206 120.4(5) ?
C208 C207 H207 119.8 ?
C206 C207 H207 119.8 ?
C209 C208 C207 118.7(5) ?
C209 C208 H208 120.7 ?
C207 C208 H208 120.7 ?
C208 C209 C210 122.8(5) ?
C208 C209 Cl2 118.8(4) ?
C210 C209 Cl2 118.5(4) ?
C209 C210 C211 118.1(5) ?
C209 C210 H210 120.9 ?
C211 C210 H210 120.9 ?
C206 C211 C210 121.4(5) ?
C206 C211 H211 119.3 ?
C210 C211 H211 119.3 ?
O21 C212 C213 105.7(4) ?
O21 C212 H22 110.6 ?
C213 C212 H22 110.6 ?
O21 C212 H21 110.6 ?
C213 C212 H21 110.6 ?
H22 C212 H21 108.7 ?
C212 C213 C214 112.9(4) ?
C212 C213 H24 109.0 ?
C214 C213 H24 109.0 ?
C212 C213 H23 109.0 ?
C214 C213 H23 109.0 ?
H24 C213 H23 107.8 ?
C215 C214 C213 116.0(4) ?
C215 C214 H25 108.3 ?
C213 C214 H25 108.3 ?
C215 C214 H26 108.3 ?
C213 C214 H26 108.3 ?
H25 C214 H26 107.4 ?
C216 C215 C217 121.2(5) ?
C216 C215 C214 124.3(5) ?
C217 C215 C214 114.5(4) ?
C215 C216 H27 120.0 ?
C215 C216 H28 120.0 ?
H27 C216 H28 120.0 ?
C218 C217 C222 116.8(5) ?
C218 C217 C215 122.1(4) ?
C222 C217 C215 121.1(5) ?
C219 C218 C217 122.5(5) ?
C219 C218 H218 118.8 ?
C217 C218 H218 118.8 ?
C220 C219 C218 118.8(6) ?
C220 C219 H219 120.6 ?
C218 C219 H219 120.6 ?
C221 C220 C219 120.7(6) ?
C221 C220 H220 119.7 ?
C219 C220 H220 119.7 ?
C220 C221 C222 121.1(5) ?
C220 C221 H221 119.5 ?
C222 C221 H221 119.5 ?
C221 C222 C217 120.1(6) ?
C221 C222 H222 119.9 ?
C217 C222 H222 119.9 ?
C205 S21 C202 92.3(2) yes
N33 O31 C312 110.1(3) ?
N33 C302 S32 129.6(3) ?
N33 C302 S31 105.6(3) yes
S32 C302 S31 124.8(3) ?
C302 N33 O31 120.2(3) ?
C302 N33 C304 119.1(4) yes
O31 N33 C304 120.7(4) ?
C305 C304 N33 109.0(5) yes
C305 C304 C306 127.6(5) ?
N33 C304 C306 123.4(4) ?
C304 C305 S31 113.1(4) yes
C304 C305 H305 123.5 ?
S31 C305 H305 123.5 ?
C311 C306 C307 119.4(5) ?
C311 C306 C304 122.2(5) ?
C307 C306 C304 118.3(5) ?
C308 C307 C306 119.3(6) ?
C308 C307 H307 120.3 ?
C306 C307 H307 120.3 ?
C309 C308 C307 120.2(6) ?
C309 C308 H308 119.9 ?
C307 C308 H308 119.9 ?
C308 C309 C310 121.4(5) ?
C308 C309 Cl3 119.3(5) ?
C310 C309 Cl3 119.3(5) ?
C309 C310 C311 119.0(5) ?
C309 C310 H310 120.5 ?
C311 C310 H310 120.5 ?
C310 C311 C306 120.6(5) ?
C310 C311 H311 119.7 ?
C306 C311 H311 119.7 ?
O31 C312 C313 106.3(4) ?
O31 C312 H31 110.5 ?
C313 C312 H31 110.5 ?
O31 C312 H32 110.5 ?
C313 C312 H32 110.5 ?
H31 C312 H32 108.7 ?
C312 C313 C314 112.4(4) ?
C312 C313 H34 109.1 ?
C314 C313 H34 109.1 ?
C312 C313 H33 109.1 ?
C314 C313 H33 109.1 ?
H34 C313 H33 107.8 ?
C313 C314 C315 116.2(4) ?
C313 C314 H35 108.2 ?
C315 C314 H35 108.2 ?
C313 C314 H36 108.2 ?
C315 C314 H36 108.2 ?
H35 C314 H36 107.4 ?
C316 C315 C317 122.3(4) ?
C316 C315 C314 122.9(5) ?
C317 C315 C314 114.7(4) ?
C315 C316 H38 120.0 ?
C315 C316 H37 120.0 ?
H38 C316 H37 120.0 ?
C318 C317 C322 117.2(5) ?
C318 C317 C315 121.7(4) ?
C322 C317 C315 121.1(4) ?
C319 C318 C317 121.8(5) ?
C319 C318 H318 119.1 ?
C317 C318 H318 119.1 ?
C320 C319 C318 119.7(6) ?
C320 C319 H319 120.1 ?
C318 C319 H319 120.1 ?
C321 C320 C319 120.3(5) ?
C321 C320 H320 119.9 ?
C319 C320 H320 119.9 ?
C320 C321 C322 119.9(5) ?
C320 C321 H321 120.1 ?
C322 C321 H321 120.1 ?
C321 C322 C317 121.1(5) ?
C321 C322 H322 119.5 ?
C317 C322 H322 119.5 ?
C305 S31 C302 93.3(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O11 N13 1.387(4) yes
O11 C112 1.464(6) ?
C102 N13 1.356(6) yes
C102 S12 1.650(6) yes
C102 S11 1.737(5) yes
N13 C104 1.393(6) yes
C104 C105 1.350(7) yes
C104 C106 1.481(7) ?
C105 S11 1.706(7) yes
C105 H105 0.9300 ?
C106 C111 1.388(7) ?
C106 C107 1.393(7) ?
C107 C108 1.365(9) ?
C107 H107 0.9300 ?
C108 C109 1.362(8) ?
C108 H108 0.9300 ?
C109 C110 1.377(8) ?
C109 Cl1 1.747(6) ?
C110 C111 1.405(7) ?
C110 H110 0.9300 ?
C111 H111 0.9300 ?
C112 C113 1.511(6) ?
C112 H11 0.9700 ?
C112 H12 0.9700 ?
C113 C114 1.479(6) ?
C113 H13 0.9700 ?
C113 H14 0.9700 ?
C114 C115 1.517(6) ?
C114 H15 0.9700 ?
C114 H16 0.9700 ?
C115 C116 1.295(7) ?
C115 C117 1.489(7) ?
C116 H17 0.9300 ?
C116 H18 0.9300 ?
C117 C122 1.394(7) ?
C117 C118 1.402(7) ?
C118 C119 1.373(7) ?
C118 H118 0.9300 ?
C119 C120 1.375(8) ?
C119 H119 0.9300 ?
C120 C121 1.360(8) ?
C120 H120 0.9300 ?
C121 C122 1.382(7) ?
C121 H121 0.9300 ?
C122 H122 0.9300 ?
O21 N23 1.391(4) yes
O21 C212 1.457(6) ?
C202 N23 1.336(6) yes
C202 S22 1.669(6) yes
C202 S21 1.733(5) yes
N23 C204 1.397(6) yes
C204 C205 1.336(6) yes
C204 C206 1.479(6) ?
C205 S21 1.724(6) yes
C205 H205 0.9300 ?
C206 C211 1.372(6) ?
C206 C207 1.401(7) ?
C207 C208 1.384(7) ?
C207 H207 0.9300 ?
C208 C209 1.365(8) ?
C208 H208 0.9300 ?
C209 C210 1.365(7) ?
C209 Cl2 1.757(5) ?
C210 C211 1.387(6) ?
C210 H210 0.9300 ?
C211 H211 0.9300 ?
C212 C213 1.513(6) ?
C212 H22 0.9700 ?
C212 H21 0.9700 ?
C213 C214 1.523(6) ?
C213 H24 0.9700 ?
C213 H23 0.9700 ?
C214 C215 1.514(6) ?
C214 H25 0.9700 ?
C214 H26 0.9700 ?
C215 C216 1.289(8) ?
C215 C217 1.498(7) ?
C216 H27 0.9300 ?
C216 H28 0.9300 ?
C217 C218 1.388(7) ?
C217 C222 1.404(7) ?
C218 C219 1.386(7) ?
C218 H218 0.9300 ?
C219 C220 1.368(7) ?
C219 H219 0.9300 ?
C220 C221 1.352(8) ?
C220 H220 0.9300 ?
C221 C222 1.389(8) ?
C221 H221 0.9300 ?
C222 H222 0.9300 ?
O31 N33 1.387(4) yes
O31 C312 1.472(6) ?
C302 N33 1.360(6) yes
C302 S32 1.646(5) yes
C302 S31 1.742(4) yes
N33 C304 1.400(6) yes
C304 C305 1.350(7) yes
C304 C306 1.474(7) ?
C305 S31 1.697(7) yes
C305 H305 0.9300 ?
C306 C311 1.385(7) ?
C306 C307 1.389(7) ?
C307 C308 1.382(9) ?
C307 H307 0.9300 ?
C308 C309 1.364(9) ?
C308 H308 0.9300 ?
C309 C310 1.365(8) ?
C309 Cl3 1.749(5) ?
C310 C311 1.381(7) ?
C310 H310 0.9300 ?
C311 H311 0.9300 ?
C312 C313 1.509(6) ?
C312 H31 0.9700 ?
C312 H32 0.9700 ?
C313 C314 1.517(6) ?
C313 H34 0.9700 ?
C313 H33 0.9700 ?
C314 C315 1.529(6) ?
C314 H35 0.9700 ?
C314 H36 0.9700 ?
C315 C316 1.288(7) ?
C315 C317 1.490(6) ?
C316 H38 0.9300 ?
C316 H37 0.9300 ?
C317 C318 1.384(7) ?
C317 C322 1.394(6) ?
C318 C319 1.378(8) ?
C318 H318 0.9300 ?
C319 C320 1.372(8) ?
C319 H319 0.9300 ?
C320 C321 1.367(7) ?
C320 H320 0.9300 ?
C321 C322 1.389(7) ?
C321 H321 0.9300 ?
C322 H322 0.9300 ?
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
_geom_torsion_publ_flag
S12 C102 N13 O11 0.8(8) ?
S11 C102 N13 O11 -179.5(3) ?
S12 C102 N13 C104 179.9(5) ?
S11 C102 N13 C104 -0.4(7) ?
C112 O11 N13 C102 -84.3(5) yes
C112 O11 N13 C104 96.6(5) ?
C102 N13 C104 C105 0.7(8) ?
O11 N13 C104 C105 179.8(5) ?
C102 N13 C104 C106 178.4(5) ?
O11 N13 C104 C106 -2.5(8) ?
N13 C104 C105 S11 -0.6(7) ?
C106 C104 C105 S11 -178.3(5) ?
C105 C104 C106 C111 -142.5(6) ?
N13 C104 C106 C111 40.1(8) yes
C105 C104 C106 C107 35.2(9) ?
N13 C104 C106 C107 -142.2(6) ?
C111 C106 C107 C108 0.8(8) ?
C104 C106 C107 C108 -177.0(5) ?
C106 C107 C108 C109 -2.5(9) ?
C107 C108 C109 C110 2.2(9) ?
C107 C108 C109 Cl1 -178.0(5) ?
C108 C109 C110 C111 -0.3(9) ?
Cl1 C109 C110 C111 179.9(4) ?
C107 C106 C111 C110 1.1(8) ?
C104 C106 C111 C110 178.9(5) ?
C109 C110 C111 C106 -1.3(8) ?
N13 O11 C112 C113 -177.9(4) ?
O11 C112 C113 C114 71.3(6) yes
C112 C113 C114 C115 173.9(5) yes
C113 C114 C115 C116 -0.8(10) yes
C113 C114 C115 C117 -178.5(5) ?
C116 C115 C117 C122 20.1(10) yes
C114 C115 C117 C122 -162.2(5) ?
C116 C115 C117 C118 -162.0(8) ?
C114 C115 C117 C118 15.8(8) ?
C122 C117 C118 C119 -1.7(9) ?
C115 C117 C118 C119 -179.7(6) ?
C117 C118 C119 C120 0.9(10) ?
C118 C119 C120 C121 -0.3(10) ?
C119 C120 C121 C122 0.6(10) ?
C120 C121 C122 C117 -1.5(10) ?
C118 C117 C122 C121 2.0(9) ?
C115 C117 C122 C121 -180.0(6) ?
C104 C105 S11 C102 0.4(6) ?
N13 C102 S11 C105 0.0(5) ?
S12 C102 S11 C105 179.7(5) ?
S22 C202 N23 O21 3.8(9) ?
S21 C202 N23 O21 -173.6(4) ?
S22 C202 N23 C204 173.5(5) ?
S21 C202 N23 C204 -3.9(7) ?
C212 O21 N23 C202 -77.0(6) yes
C212 O21 N23 C204 113.6(5) ?
C202 N23 C204 C205 2.7(8) ?
O21 N23 C204 C205 172.4(5) ?
C202 N23 C204 C206 -174.7(5) ?
O21 N23 C204 C206 -5.0(8) ?
N23 C204 C205 S21 -0.1(7) ?
C206 C204 C205 S21 177.3(5) ?
C205 C204 C206 C211 135.6(7) ?
N23 C204 C206 C211 -47.4(8) yes
C205 C204 C206 C207 -42.2(9) ?
N23 C204 C206 C207 134.8(6) ?
C211 C206 C207 C208 -0.2(8) ?
C204 C206 C207 C208 177.7(5) ?
C206 C207 C208 C209 1.6(10) ?
C207 C208 C209 C210 -1.2(9) ?
C207 C208 C209 Cl2 178.1(5) ?
C208 C209 C210 C211 -0.5(8) ?
Cl2 C209 C210 C211 -179.8(4) ?
C207 C206 C211 C210 -1.5(8) ?
C204 C206 C211 C210 -179.3(5) ?
C209 C210 C211 C206 1.9(8) ?
N23 O21 C212 C213 -179.3(3) ?
O21 C212 C213 C214 64.6(5) yes
C212 C213 C214 C215 173.6(5) yes
C213 C214 C215 C216 10.7(9) yes
C213 C214 C215 C217 -170.3(5) ?
C216 C215 C217 C218 149.7(7) ?
C214 C215 C217 C218 -29.4(8) ?
C216 C215 C217 C222 -31.9(9) yes
C214 C215 C217 C222 149.0(5) ?
C222 C217 C218 C219 3.1(9) ?
C215 C217 C218 C219 -178.5(5) ?
C217 C218 C219 C220 -2.2(9) ?
C218 C219 C220 C221 0.8(9) ?
C219 C220 C221 C222 -0.4(9) ?
C220 C221 C222 C217 1.4(9) ?
C218 C217 C222 C221 -2.6(8) ?
C215 C217 C222 C221 178.9(5) ?
C204 C205 S21 C202 -1.8(6) ?
N23 C202 S21 C205 3.1(5) ?
S22 C202 S21 C205 -174.5(5) ?
S32 C302 N33 O31 0.7(8) ?
S31 C302 N33 O31 -178.6(4) ?
S32 C302 N33 C304 -180.0(5) ?
S31 C302 N33 C304 0.7(6) ?
C312 O31 N33 C302 -82.9(5) yes
C312 O31 N33 C304 97.8(5) ?
C302 N33 C304 C305 -0.9(8) ?
O31 N33 C304 C305 178.4(5) ?
C302 N33 C304 C306 178.8(5) ?
O31 N33 C304 C306 -1.9(8) ?
N33 C304 C305 S31 0.6(7) ?
C306 C304 C305 S31 -179.0(5) ?
C305 C304 C306 C311 -133.0(6) ?
N33 C304 C306 C311 47.4(8) yes
C305 C304 C306 C307 43.0(9) ?
N33 C304 C306 C307 -136.6(6) ?
C311 C306 C307 C308 -0.7(9) ?
C304 C306 C307 C308 -176.8(6) ?
C306 C307 C308 C309 1.6(11) ?
C307 C308 C309 C310 -1.2(11) ?
C307 C308 C309 Cl3 177.9(6) ?
C308 C309 C310 C311 0.0(9) ?
Cl3 C309 C310 C311 -179.1(4) ?
C309 C310 C311 C306 0.9(8) ?
C307 C306 C311 C310 -0.5(8) ?
C304 C306 C311 C310 175.4(5) ?
N33 O31 C312 C313 -176.4(3) ?
O31 C312 C313 C314 69.9(5) yes
C312 C313 C314 C315 172.8(4) yes
C313 C314 C315 C316 10.6(9) yes
C313 C314 C315 C317 -167.9(5) ?
C316 C315 C317 C318 149.5(7) ?
C314 C315 C317 C318 -32.0(7) ?
C316 C315 C317 C322 -31.7(9) yes
C314 C315 C317 C322 146.8(5) ?
C322 C317 C318 C319 -0.3(8) ?
C315 C317 C318 C319 178.6(5) ?
C317 C318 C319 C320 0.7(9) ?
C318 C319 C320 C321 -0.5(9) ?
C319 C320 C321 C322 -0.2(8) ?
C320 C321 C322 C317 0.7(8) ?
C318 C317 C322 C321 -0.4(8) ?
C315 C317 C322 C321 -179.3(5) ?
C304 C305 S31 C302 -0.2(6) ?
N33 C302 S31 C305 -0.2(5) ?
S32 C302 S31 C305 -179.6(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24725649
2 PubChem 139059864
