#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/98/2229808.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_2229808
loop_
_publ_author_name
'Akkurt, Mehmet'
'Çelik, Ísmail'
'Demir, Hale'
'Özkırımlı, Sumru'
'Büyükgüngör, Orhan'
_publ_section_title
;
 N-[2-(4-Chlorophenyl)-5-methyl-4-oxo-1,3-thiazolidin-3-yl]pyridine-3-carboxamide
;
_journal_coeditor_code           QM2002
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o745
_journal_page_last               o746
_journal_paper_doi               10.1107/S1600536811007136
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H14 Cl N3 O2 S'
_chemical_formula_moiety         'C16 H14 Cl N3 O2 S'
_chemical_formula_sum            'C16 H14 Cl N3 O2 S'
_chemical_formula_weight         347.82
_chemical_name_systematic
;
N-[2-(4-Chlorophenyl)-5-methyl-4-oxo-1,3-thiazolidin-3-yl]pyridine-3-
carboxamide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                91.798(5)
_cell_angle_beta                 100.282(5)
_cell_angle_gamma                98.068(5)
_cell_formula_units_Z            4
_cell_length_a                   11.4481(7)
_cell_length_b                   12.0276(7)
_cell_length_c                   12.5556(7)
_cell_measurement_reflns_used    29172
_cell_measurement_temperature    296
_cell_measurement_theta_max      28.14
_cell_measurement_theta_min      1.83
_cell_volume                     1681.39(17)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS 2'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0785
_diffrn_reflns_av_sigmaI/netI    0.0645
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            27641
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        27.65
_diffrn_reflns_theta_max         27.65
_diffrn_reflns_theta_min         2.23
_exptl_absorpt_coefficient_mu    0.363
_exptl_absorpt_correction_T_max  0.918
_exptl_absorpt_correction_T_min  0.772
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.750
_exptl_crystal_size_mid          0.460
_exptl_crystal_size_min          0.240
_refine_diff_density_max         0.662
_refine_diff_density_min         -0.355
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     472
_refine_ls_number_reflns         7719
_refine_ls_number_restraints     22
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1547
_refine_ls_R_factor_gt           0.0788
_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)+(0.1067P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1871
_refine_ls_wR_factor_ref         0.2245
_reflns_number_gt                3832
_reflns_number_total             7719
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            qm2002.cif
_cod_data_source_block           I
_cod_database_code               2229808
_cod_database_fobs_code          2229808
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Cl Cl1 0.8901(3) 0.6468(2) -0.35513(17) 0.1812(13) Uani . . 1.000
S S1A 0.7796(8) 0.5821(6) 0.1573(6) 0.138(3) Uani . . 0.509(7)
O O1A 0.6878(18) 0.2824(10) 0.2212(17) 0.144(7) Uani . . 0.509(7)
O O2 0.4901(3) 0.2917(3) -0.0056(4) 0.1164(16) Uani . . 1.000
N N1 0.7159(3) 0.3872(2) 0.0735(3) 0.0690(11) Uani . . 1.000
N N2 0.6874(3) 0.2946(2) 0.0007(3) 0.0648(11) Uani . . 1.000
N N3 0.6148(3) 0.0002(3) -0.2017(3) 0.0734(12) Uani . . 1.000
C C1 0.8487(4) 0.4981(4) -0.0856(4) 0.0818(17) Uani . . 1.000
C C2 0.8909(5) 0.5318(5) -0.1736(5) 0.103(2) Uani . . 1.000
C C3 0.8331(6) 0.5976(5) -0.2426(4) 0.099(2) Uani . . 1.000
C C4 0.7303(6) 0.6322(4) -0.2259(4) 0.099(2) Uani . . 1.000
C C5 0.6829(4) 0.5983(4) -0.1331(4) 0.0840(17) Uani . . 1.000
C C6 0.7462(4) 0.5298(3) -0.0607(3) 0.0644(11) Uani . . 1.000
C C7 0.6970(4) 0.4995(3) 0.0387(3) 0.0752(16) Uani . . 1.000
C C8A 0.7651(11) 0.4770(7) 0.2554(8) 0.1041(16) Uani . . 0.509(7)
C C9 0.7211(6) 0.3722(4) 0.1807(4) 0.1041(16) Uani . . 1.000
C C10A 0.6693(11) 0.4777(8) 0.3215(8) 0.1041(16) Uani . . 0.509(7)
C C11 0.5725(4) 0.2482(3) -0.0301(3) 0.0680(14) Uani . . 1.000
C C12 0.5490(3) 0.1396(3) -0.0971(3) 0.0580(12) Uani . . 1.000
C C13 0.4367(4) 0.0760(4) -0.1111(4) 0.0764(16) Uani . . 1.000
C C14 0.4137(4) -0.0244(4) -0.1702(4) 0.0826(17) Uani . . 1.000
C C15 0.5063(4) -0.0598(3) -0.2123(3) 0.0754(16) Uani . . 1.000
C C16 0.6341(3) 0.0984(3) -0.1448(3) 0.0619(12) Uani . . 1.000
O O1B 0.7422(14) 0.2805(11) 0.2169(16) 0.097(5) Uani . . 0.491(7)
C C8B 0.7113(12) 0.4845(6) 0.2354(7) 0.1041(16) Uani . . 0.491(7)
S S1B 0.7748(4) 0.5927(4) 0.1577(4) 0.0654(15) Uani . . 0.491(7)
C C10B 0.7736(12) 0.4965(8) 0.3510(7) 0.1041(16) Uani . . 0.491(7)
Cl Cl2 0.58109(15) 0.34663(14) 0.67393(16) 0.1325(7) Uani . . 1.000
S S2B 0.2083(8) -0.1467(6) 0.5623(5) 0.0859(16) Uani . . 0.536(14)
O O3B 0.1523(12) -0.2164(15) 0.2601(9) 0.077(3) Uani . . 0.536(14)
O O4 -0.0346(3) -0.0194(3) 0.2833(3) 0.0987(15) Uani . . 1.000
N N4 0.1814(3) -0.0645(3) 0.3760(3) 0.0704(11) Uani . . 1.000
N N5 0.1663(3) 0.0090(3) 0.2930(3) 0.0678(12) Uani . . 1.000
N N6 -0.0872(3) 0.2001(3) 0.0369(3) 0.0813(14) Uani . . 1.000
C C17 0.2708(4) 0.1416(3) 0.6150(3) 0.0731(16) Uani . . 1.000
C C18 0.3620(4) 0.2248(4) 0.6595(4) 0.0828(17) Uani . . 1.000
C C19 0.4657(4) 0.2409(4) 0.6175(4) 0.0824(16) Uani . . 1.000
C C20 0.4777(4) 0.1736(4) 0.5301(4) 0.0919(17) Uani . . 1.000
C C21 0.3865(4) 0.0890(4) 0.4873(4) 0.0815(17) Uani . . 1.000
C C22 0.2809(4) 0.0725(3) 0.5280(3) 0.0665(12) Uani . . 1.000
C C23 0.1813(4) -0.0218(3) 0.4866(3) 0.0732(16) Uani . . 1.000
C C24B 0.1630(9) -0.2483(8) 0.4489(6) 0.073(4) Uani . . 0.536(14)
C C25 0.1511(5) -0.1769(4) 0.3519(3) 0.0892(19) Uani . . 1.000
C C26B 0.0360(10) -0.3105(13) 0.4355(10) 0.109(5) Uani . . 0.536(14)
C C27 0.0520(4) 0.0210(3) 0.2470(3) 0.0698(14) Uani . . 1.000
C C28 0.0399(3) 0.0915(3) 0.1506(3) 0.0609(12) Uani . . 1.000
C C29 0.1235(4) 0.1093(3) 0.0831(3) 0.0686(14) Uani . . 1.000
C C30 0.1012(4) 0.1714(3) -0.0052(4) 0.0742(16) Uani . . 1.000
C C31 -0.0038(4) 0.2152(3) -0.0245(4) 0.0777(16) Uani . . 1.000
C C32 -0.0642(4) 0.1396(4) 0.1230(4) 0.0744(16) Uani . . 1.000
O O3A 0.1055(17) -0.222(2) 0.2615(11) 0.112(6) Uani . . 0.464(14)
S S2A 0.1797(13) -0.1417(6) 0.5686(7) 0.124(4) Uani . . 0.464(14)
C C26A 0.125(2) -0.3496(9) 0.4571(12) 0.129(8) Uani . . 0.464(14)
C C24A 0.1067(14) -0.2284(8) 0.4507(8) 0.084(5) Uani . . 0.464(14)
H H4 0.69110 0.67770 -0.27450 0.1190 Uiso calc R 1.000
H H5 0.61180 0.62040 -0.12010 0.1000 Uiso calc R 1.000
H H7 0.61160 0.50710 0.02850 0.0900 Uiso calc R 1.000
H H8A 0.84280 0.47200 0.30120 0.1250 Uiso calc . 0.509(7)
H H10A 0.68990 0.54090 0.37330 0.1560 Uiso calc . 0.509(7)
H H10B 0.66180 0.40940 0.35890 0.1560 Uiso calc . 0.509(7)
H H2 0.96150 0.50930 -0.18740 0.1230 Uiso calc R 1.000
H H13 0.37660 0.10150 -0.08030 0.0920 Uiso calc R 1.000
H H14 0.33810 -0.06750 -0.18170 0.1000 Uiso calc R 1.000
H H15 0.49220 -0.12940 -0.25030 0.0900 Uiso calc R 1.000
H H16 0.70960 0.14150 -0.13690 0.0740 Uiso calc R 1.000
H H1 0.89030 0.45170 -0.03990 0.0980 Uiso calc R 1.000
H HN2 0.749(2) 0.262(3) 0.002(3) 0.0740 Uiso . . 1.000
H H10C 0.59440 0.48320 0.27480 0.1560 Uiso calc . 0.509(7)
H H8B 0.62630 0.49040 0.23240 0.1250 Uiso calc . 0.491(7)
H H10D 0.76410 0.56750 0.38270 0.1560 Uiso calc . 0.491(7)
H H10E 0.85750 0.49290 0.35460 0.1560 Uiso calc . 0.491(7)
H H10F 0.73940 0.43670 0.39000 0.1560 Uiso calc . 0.491(7)
H H20 0.54700 0.18550 0.50050 0.1100 Uiso calc R 1.000
H H21 0.39560 0.04200 0.43000 0.0980 Uiso calc R 1.000
H H18 0.35390 0.27040 0.71810 0.1000 Uiso calc R 1.000
H H24B 0.22180 -0.29980 0.44640 0.0880 Uiso calc . 0.536(14)
H H26D 0.03210 -0.36400 0.49030 0.1630 Uiso calc . 0.536(14)
H H23 0.10540 0.00730 0.48570 0.0880 Uiso calc R 1.000
H H26F -0.01820 -0.25770 0.44240 0.1630 Uiso calc . 0.536(14)
H H29 0.19460 0.07880 0.09810 0.0820 Uiso calc R 1.000
H H30 0.15640 0.18380 -0.05120 0.0890 Uiso calc R 1.000
H H31 -0.01770 0.25830 -0.08440 0.0930 Uiso calc R 1.000
H H32 -0.12120 0.12880 0.16750 0.0890 Uiso calc R 1.000
H HN5 0.226(3) 0.029(4) 0.261(4) 0.0970 Uiso . . 1.000
H H26E 0.01380 -0.34920 0.36510 0.1630 Uiso calc . 0.536(14)
H H17 0.20090 0.13130 0.64370 0.0870 Uiso calc R 1.000
H H24A 0.02040 -0.22560 0.44160 0.1010 Uiso calc . 0.464(14)
H H26A 0.09860 -0.37910 0.52040 0.1940 Uiso calc . 0.464(14)
H H26B 0.20830 -0.35500 0.46130 0.1940 Uiso calc . 0.464(14)
H H26C 0.07890 -0.39210 0.39360 0.1940 Uiso calc . 0.464(14)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
N N 0.0061 0.0033 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 S1A C8A . . . 98.3(5) no
C7 S1B C8B . . . 84.7(4) no
C23 S2A C24A . . . 88.9(5) no
C23 S2B C24B . . . 97.0(4) no
N2 N1 C7 . . . 121.0(3) no
C7 N1 C9 . . . 115.8(3) no
N2 N1 C9 . . . 119.3(3) no
N1 N2 C11 . . . 119.4(3) no
C15 N3 C16 . . . 117.2(3) no
C11 N2 HN2 . . . 127(2) no
N1 N2 HN2 . . . 109(2) no
N5 N4 C23 . . . 118.1(3) no
N5 N4 C25 . . . 119.1(3) no
C23 N4 C25 . . . 118.2(3) no
N4 N5 C27 . . . 117.7(3) no
C31 N6 C32 . . . 116.8(4) no
N4 N5 HN5 . . . 118(3) no
C27 N5 HN5 . . . 122(3) no
C2 C1 C6 . . . 122.0(5) no
C1 C2 C3 . . . 121.1(6) no
Cl1 C3 C2 . . . 121.6(5) no
C2 C3 C4 . . . 121.4(5) no
Cl1 C3 C4 . . . 116.9(4) no
C3 C4 C5 . . . 119.1(5) no
C4 C5 C6 . . . 118.5(5) no
C5 C6 C7 . . . 117.3(4) no
C1 C6 C7 . . . 124.8(4) no
C1 C6 C5 . . . 117.9(4) no
N1 C7 C6 . . . 113.5(3) no
S1B C7 C6 . . . 111.5(3) no
S1B C7 N1 . . . 103.1(3) no
S1A C7 C6 . . . 112.0(4) no
S1A C7 N1 . . . 99.2(3) no
S1A C8A C10A . . . 118.9(8) no
C9 C8A C10A . . . 102.9(8) no
S1A C8A C9 . . . 100.5(6) no
S1B C8B C9 . . . 106.8(6) no
S1B C8B C10B . . . 111.3(7) no
C9 C8B C10B . . . 112.1(8) no
O1B C9 C8B . . . 132.6(10) no
N1 C9 C8B . . . 107.7(5) no
O1A C9 C8A . . . 118.5(10) no
O1B C9 N1 . . . 119.4(10) no
O1A C9 N1 . . . 125.8(10) no
N1 C9 C8A . . . 115.6(5) no
N2 C11 C12 . . . 116.7(4) no
O2 C11 N2 . . . 122.3(4) no
O2 C11 C12 . . . 121.1(4) no
C13 C12 C16 . . . 117.6(4) no
C11 C12 C13 . . . 119.0(4) no
C11 C12 C16 . . . 123.4(3) no
C12 C13 C14 . . . 120.1(4) no
C13 C14 C15 . . . 117.8(4) no
N3 C15 C14 . . . 123.6(4) no
N3 C16 C12 . . . 123.7(3) no
C2 C1 H1 . . . 119.00 no
C6 C1 H1 . . . 119.00 no
C3 C2 H2 . . . 119.00 no
C1 C2 H2 . . . 120.00 no
C3 C4 H4 . . . 121.00 no
C5 C4 H4 . . . 120.00 no
C4 C5 H5 . . . 121.00 no
C6 C5 H5 . . . 121.00 no
S1A C7 H7 . . . 111.00 no
S1B C7 H7 . . . 107.00 no
N1 C7 H7 . . . 111.00 no
C6 C7 H7 . . . 111.00 no
S1A C8A H8A . . . 111.00 no
C10A C8A H8A . . . 111.00 no
C9 C8A H8A . . . 111.00 no
C9 C8B H8B . . . 109.00 no
C10B C8B H8B . . . 109.00 no
S1B C8B H8B . . . 109.00 no
H10A C10A H10B . . . 109.00 no
H10B C10A H10C . . . 109.00 no
H10A C10A H10C . . . 109.00 no
C8A C10A H10C . . . 109.00 no
C8A C10A H10B . . . 109.00 no
C8A C10A H10A . . . 109.00 no
C8B C10B H10E . . . 109.00 no
C8B C10B H10F . . . 109.00 no
H10D C10B H10E . . . 109.00 no
H10E C10B H10F . . . 109.00 no
H10D C10B H10F . . . 110.00 no
C8B C10B H10D . . . 109.00 no
C12 C13 H13 . . . 120.00 no
C14 C13 H13 . . . 120.00 no
C15 C14 H14 . . . 121.00 no
C13 C14 H14 . . . 121.00 no
C14 C15 H15 . . . 118.00 no
N3 C15 H15 . . . 118.00 no
C12 C16 H16 . . . 118.00 no
N3 C16 H16 . . . 118.00 no
C18 C17 C22 . . . 121.1(4) no
C17 C18 C19 . . . 119.9(4) no
Cl2 C19 C18 . . . 119.8(4) no
C18 C19 C20 . . . 120.2(4) no
Cl2 C19 C20 . . . 120.0(4) no
C19 C20 C21 . . . 119.4(4) no
C20 C21 C22 . . . 121.0(4) no
C17 C22 C23 . . . 118.9(4) no
C21 C22 C23 . . . 122.7(4) no
C17 C22 C21 . . . 118.4(4) no
S2B C23 C22 . . . 109.0(4) no
S2A C23 C22 . . . 114.3(5) no
S2A C23 N4 . . . 106.3(4) no
S2B C23 N4 . . . 100.7(3) no
N4 C23 C22 . . . 113.6(3) no
S2A C24A C26A . . . 113.9(10) no
C25 C24A C26A . . . 111.0(10) no
S2A C24A C25 . . . 108.0(8) no
C25 C24B C26B . . . 100.6(8) no
S2B C24B C25 . . . 103.6(6) no
S2B C24B C26B . . . 115.6(8) no
O3B C25 N4 . . . 120.1(9) no
N4 C25 C24B . . . 114.7(5) no
O3A C25 N4 . . . 125.8(11) no
O3B C25 C24B . . . 121.4(9) no
O3A C25 C24A . . . 117.6(11) no
N4 C25 C24A . . . 106.9(5) no
N5 C27 C28 . . . 115.7(4) no
O4 C27 C28 . . . 121.7(4) no
O4 C27 N5 . . . 122.6(4) no
C29 C28 C32 . . . 116.8(4) no
C27 C28 C29 . . . 124.7(3) no
C27 C28 C32 . . . 118.5(4) no
C28 C29 C30 . . . 119.9(4) no
C29 C30 C31 . . . 118.6(4) no
N6 C31 C30 . . . 124.1(4) no
N6 C32 C28 . . . 124.0(4) no
C18 C17 H17 . . . 119.00 no
C22 C17 H17 . . . 120.00 no
C17 C18 H18 . . . 120.00 no
C19 C18 H18 . . . 120.00 no
C19 C20 H20 . . . 120.00 no
C21 C20 H20 . . . 120.00 no
C20 C21 H21 . . . 120.00 no
C22 C21 H21 . . . 119.00 no
S2B C23 H23 . . . 119.00 no
N4 C23 H23 . . . 107.00 no
C22 C23 H23 . . . 107.00 no
S2A C23 H23 . . . 107.00 no
S2A C24A H24A . . . 108.00 no
C26A C24A H24A . . . 108.00 no
C25 C24A H24A . . . 108.00 no
S2B C24B H24B . . . 112.00 no
C25 C24B H24B . . . 112.00 no
C26B C24B H24B . . . 112.00 no
C24A C26A H26A . . . 109.00 no
C24A C26A H26B . . . 110.00 no
H26A C26A H26B . . . 110.00 no
H26A C26A H26C . . . 109.00 no
C24A C26A H26C . . . 109.00 no
H26B C26A H26C . . . 110.00 no
C24B C26B H26E . . . 109.00 no
C24B C26B H26F . . . 109.00 no
C24B C26B H26D . . . 109.00 no
H26D C26B H26F . . . 110.00 no
H26E C26B H26F . . . 109.00 no
H26D C26B H26E . . . 109.00 no
C30 C29 H29 . . . 120.00 no
C28 C29 H29 . . . 120.00 no
C31 C30 H30 . . . 121.00 no
C29 C30 H30 . . . 121.00 no
N6 C31 H31 . . . 118.00 no
C30 C31 H31 . . . 118.00 no
C28 C32 H32 . . . 118.00 no
N6 C32 H32 . . . 118.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C3 . . 1.745(6) no
Cl2 C19 . . 1.733(5) no
S1A C7 . . 1.800(8) no
S1A C8A . . 1.804(12) no
S1B C8B . . 1.800(10) no
S1B C7 . . 1.850(6) no
S2A C24A . . 1.787(13) no
S2A C23 . . 1.798(8) no
S2B C24B . . 1.800(11) no
S2B C23 . . 1.836(8) no
O1A C9 . . 1.248(15) no
O1B C9 . . 1.244(15) no
O2 C11 . . 1.221(6) no
O3A C25 . . 1.235(16) no
O3B C25 . . 1.236(13) no
O4 C27 . . 1.211(6) no
N1 C7 . . 1.465(4) no
N1 C9 . . 1.356(6) no
N1 N2 . . 1.382(4) no
N2 C11 . . 1.338(6) no
N3 C15 . . 1.328(6) no
N3 C16 . . 1.331(5) no
N2 HN2 . . 0.85(3) no
N4 C23 . . 1.466(5) no
N4 C25 . . 1.358(6) no
N4 N5 . . 1.391(5) no
N5 C27 . . 1.362(6) no
N6 C31 . . 1.327(6) no
N6 C32 . . 1.330(6) no
N5 HN5 . . 0.86(4) no
C1 C2 . . 1.335(8) no
C1 C6 . . 1.367(7) no
C2 C3 . . 1.342(8) no
C3 C4 . . 1.350(10) no
C4 C5 . . 1.418(7) no
C5 C6 . . 1.418(6) no
C6 C7 . . 1.493(6) no
C8A C9 . . 1.517(10) no
C8A C10A . . 1.490(17) no
C8B C10B . . 1.492(13) no
C8B C9 . . 1.523(10) no
C11 C12 . . 1.496(5) no
C12 C16 . . 1.371(5) no
C12 C13 . . 1.380(6) no
C13 C14 . . 1.365(7) no
C14 C15 . . 1.377(7) no
C1 H1 . . 0.9300 no
C2 H2 . . 0.9300 no
C4 H4 . . 0.9300 no
C5 H5 . . 0.9300 no
C7 H7 . . 0.9800 no
C8A H8A . . 0.9800 no
C8B H8B . . 0.9800 no
C10A H10B . . 0.9600 no
C10A H10A . . 0.9600 no
C10A H10C . . 0.9600 no
C10B H10E . . 0.9600 no
C10B H10F . . 0.9600 no
C10B H10D . . 0.9600 no
C13 H13 . . 0.9300 no
C14 H14 . . 0.9300 no
C15 H15 . . 0.9300 no
C16 H16 . . 0.9300 no
C17 C22 . . 1.383(5) no
C17 C18 . . 1.366(6) no
C18 C19 . . 1.375(7) no
C19 C20 . . 1.381(7) no
C20 C21 . . 1.372(7) no
C21 C22 . . 1.386(7) no
C22 C23 . . 1.498(6) no
C24A C25 . . 1.538(12) no
C24A C26A . . 1.504(16) no
C24B C25 . . 1.510(9) no
C24B C26B . . 1.517(16) no
C27 C28 . . 1.497(5) no
C28 C29 . . 1.387(6) no
C28 C32 . . 1.391(6) no
C29 C30 . . 1.363(6) no
C30 C31 . . 1.365(6) no
C17 H17 . . 0.9300 no
C18 H18 . . 0.9300 no
C20 H20 . . 0.9300 no
C21 H21 . . 0.9300 no
C23 H23 . . 0.9800 no
C24A H24A . . 0.9800 no
C24B H24B . . 0.9800 no
C26A H26A . . 0.9600 no
C26A H26B . . 0.9600 no
C26A H26C . . 0.9600 no
C26B H26D . . 0.9600 no
C26B H26E . . 0.9600 no
C26B H26F . . 0.9600 no
C29 H29 . . 0.9300 no
C30 H30 . . 0.9300 no
C31 H31 . . 0.9300 no
C32 H32 . . 0.9300 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Cl1 C26B 3.373(13) . 1_664 no
Cl1 H26D 2.7600 . 1_664 no
Cl1 H26F 3.1100 . 1_664 no
Cl1 H26A 3.1200 . 1_664 no
Cl2 H24B 3.0400 . 2_656 no
S2A O4 3.428(12) . 2_556 no
S2A O1A 3.42(2) . 2_656 no
S1A H18 3.0600 . 2_666 no
S1B H18 2.9400 . 2_666 no
S1B H30 3.1100 . 2_665 no
S2B H20 3.1300 . 2_656 no
O1A N2 2.78(2) . . no
O1A C11 3.19(2) . . no
O1A C14 3.160(14) . 2_655 no
O1A S2A 3.42(2) . 2_656 no
O1A C15 3.216(16) . 2_655 no
O1B N2 2.69(2) . . no
O1B C11 3.33(2) . . no
O1B C32 3.322(17) . 1_655 no
O1B C14 3.315(15) . 2_655 no
O2 N1 2.677(5) . . no
O2 C7 3.154(5) . . no
O2 C9 3.215(7) . . no
O2 C5 3.245(6) . 2_665 no
O3A C31 3.004(15) . 2_555 no
O3A O4 3.13(2) . . no
O3A C27 3.07(2) . . no
O3A N5 2.77(2) . . no
O3B C27 3.222(18) . . no
O3B C31 3.139(13) . 2_555 no
O3B N5 2.707(18) . . no
O3B C16 3.242(15) . 2_655 no
O4 O3A 3.13(2) . . no
O4 S2A 3.428(12) . 2_556 no
O4 C25 3.071(6) . . no
O4 C23 3.225(5) . . no
O4 N4 2.674(5) . . no
O4 C17 3.367(6) . 2_556 no
O1A H10C 2.8800 . . no
O1A H15 2.6500 . 2_655 no
O1A H14 2.5800 . 2_655 no
O1A H10B 2.3600 . . no
O1B H32 2.6900 . 1_655 no
O1B H14 2.5900 . 2_655 no
O1B H10F 2.8400 . . no
O1B HN2 2.72(4) . . no
O2 H7 2.8300 . 2_665 no
O2 H5 2.4200 . 2_665 no
O2 H13 2.5300 . . no
O2 H7 2.7500 . . no
O3A H26C 2.6900 . . no
O3A H31 2.2700 . 2_555 no
O3B H31 2.4500 . 2_555 no
O3B H26E 2.6400 . . no
O3B H16 2.5000 . 2_655 no
O4 H17 2.5000 . 2_556 no
O4 H32 2.5300 . . no
O4 H23 2.7300 . . no
N1 O2 2.677(5) . . no
N2 C1 3.192(6) . . no
N2 O1A 2.78(2) . . no
N2 N6 2.932(5) . 1_655 no
N2 O1B 2.69(2) . . no
N3 N5 2.950(5) . 2_655 no
N4 O4 2.674(5) . . no
N5 N3 2.950(5) . 2_655 no
N5 C21 3.195(6) . . no
N5 O3A 2.77(2) . . no
N5 O3B 2.707(18) . . no
N6 N2 2.932(5) . 1_455 no
N1 H1 2.7000 . . no
N2 H1 2.9100 . . no
N2 H16 2.5600 . . no
N3 H29 2.6500 . 2_655 no
N3 HN5 2.16(4) . 2_655 no
N3 H21 2.8700 . 2_655 no
N4 H21 2.5700 . . no
N5 H21 2.8400 . . no
N5 H29 2.6700 . . no
N6 HN2 2.09(3) . 1_455 no
N6 H16 2.8800 . 1_455 no
C1 N2 3.192(6) . . no
C4 C29 3.578(6) . 2_665 no
C5 O2 3.245(6) . 2_665 no
C7 O2 3.154(5) . . no
C9 O2 3.215(7) . . no
C11 O1A 3.19(2) . . no
C11 O1B 3.33(2) . . no
C13 C13 3.584(7) . 2_655 no
C13 C18 3.479(7) . 1_554 no
C14 O1A 3.160(14) . 2_655 no
C14 O1B 3.315(15) . 2_655 no
C15 O1A 3.216(16) . 2_655 no
C16 O3B 3.242(15) . 2_655 no
C17 O4 3.367(6) . 2_556 no
C18 C13 3.479(7) . 1_556 no
C21 C21 3.570(7) . 2_656 no
C21 N5 3.195(6) . . no
C23 O4 3.225(5) . . no
C25 O4 3.071(6) . . no
C26B Cl1 3.373(13) . 1_446 no
C27 O3B 3.222(18) . . no
C27 O3A 3.07(2) . . no
C29 C4 3.578(6) . 2_665 no
C31 O3B 3.139(13) . 2_555 no
C31 O3A 3.004(15) . 2_555 no
C32 O1B 3.322(17) . 1_455 no
C1 H1 3.0900 . 2_765 no
C16 HN2 2.68(4) . . no
C16 H29 3.0900 . 2_655 no
C16 HN5 2.90(4) . 2_655 no
C18 H10D 3.0700 . 2_666 no
C18 H10A 2.9900 . 2_666 no
C21 HN5 3.10(5) . . no
C27 H23 2.9600 . . no
C29 HN5 2.61(5) . . no
C31 HN2 3.03(3) . 1_455 no
C32 HN2 2.99(3) . 1_455 no
H1 N2 2.9100 . . no
H1 C1 3.0900 . 2_765 no
H1 N1 2.7000 . . no
HN2 O1B 2.72(4) . . no
HN2 N6 2.09(3) . 1_655 no
HN2 C31 3.03(3) . 1_655 no
HN2 C16 2.68(4) . . no
HN2 C32 2.99(3) . 1_655 no
HN2 H16 2.1700 . . no
HN5 H29 2.1300 . . no
HN5 C29 2.61(5) . . no
HN5 H21 2.5900 . . no
HN5 N3 2.16(4) . 2_655 no
HN5 C21 3.10(5) . . no
HN5 C16 2.90(4) . 2_655 no
H5 H7 2.3400 . . no
H5 O2 2.4200 . 2_665 no
H7 H7 2.5100 . 2_665 no
H7 H8B 2.5500 . . no
H7 H5 2.3400 . . no
H7 O2 2.8300 . 2_665 no
H7 O2 2.7500 . . no
H8A H26A 2.5600 . 2_656 no
H8B H7 2.5500 . . no
H10A C18 2.9900 . 2_666 no
H10B O1A 2.3600 . . no
H10C O1A 2.8800 . . no
H10D C18 3.0700 . 2_666 no
H10F O1B 2.8400 . . no
H13 O2 2.5300 . . no
H14 H32 2.5300 . 2_555 no
H14 O1B 2.5900 . 2_655 no
H14 O1A 2.5800 . 2_655 no
H15 O1A 2.6500 . 2_655 no
H16 N2 2.5600 . . no
H16 N6 2.8800 . 1_655 no
H16 HN2 2.1700 . . no
H16 O3B 2.5000 . 2_655 no
H17 H23 2.4400 . . no
H17 O4 2.5000 . 2_556 no
H18 S1A 3.0600 . 2_666 no
H18 S1B 2.9400 . 2_666 no
H20 S2B 3.1300 . 2_656 no
H21 HN5 2.5900 . . no
H21 N4 2.5700 . . no
H21 N5 2.8400 . . no
H21 N3 2.8700 . 2_655 no
H23 H17 2.4400 . . no
H23 O4 2.7300 . . no
H23 C27 2.9600 . . no
H23 H23 2.4900 . 2_556 no
H24B Cl2 3.0400 . 2_656 no
H26A H8A 2.5600 . 2_656 no
H26A Cl1 3.1200 . 1_446 no
H26C O3A 2.6900 . . no
H26D Cl1 2.7600 . 1_446 no
H26E O3B 2.6400 . . no
H26F Cl1 3.1100 . 1_446 no
H29 N5 2.6700 . . no
H29 HN5 2.1300 . . no
H29 C16 3.0900 . 2_655 no
H29 N3 2.6500 . 2_655 no
H30 S1B 3.1100 . 2_665 no
H31 O3A 2.2700 . 2_555 no
H31 O3B 2.4500 . 2_555 no
H32 H14 2.5300 . 2_555 no
H32 O4 2.5300 . . no
H32 O1B 2.6900 . 1_455 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
_geom_hbond_publ_flag
N2 HN2 N6 1_655 0.85(3) 2.09(3) 2.932(5) 168(3) yes
N5 HN5 N3 2_655 0.86(4) 2.16(4) 2.950(5) 153(4) yes
C5 H5 O2 2_665 0.93 2.42 3.245(6) 147 yes
C14 H14 O1A 2_655 0.93 2.58 3.160(14) 121 yes
C16 H16 N2 . 0.93 2.56 2.865(5) 100 ?
C16 H16 O3B 2_655 0.93 2.50 3.242(15) 136 yes
C17 H17 O4 2_556 0.93 2.50 3.367(6) 155 yes
C21 H21 N4 . 0.93 2.57 2.885(6) 101 ?
C26B H26D Cl1 1_446 0.96 2.76 3.373(13) 123 yes
C31 H31 O3B 2_555 0.93 2.45 3.139(13) 131 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
C8A S1A C7 N1 . . . . -26.5(6) no
C8A S1A C7 C6 . . . . -146.5(5) no
C7 S1A C8A C9 . . . . 13.9(8) no
C7 S1A C8A C10A . . . . -97.4(8) no
C23 S2B C24B C26B . . . . -98.4(9) no
C24B S2B C23 N4 . . . . -19.7(6) no
C24B S2B C23 C22 . . . . -139.5(5) no
C23 S2B C24B C25 . . . . 10.6(7) no
C9 N1 N2 C11 . . . . 79.5(5) no
C9 N1 C7 S1A . . . . 34.4(6) no
N2 N1 C7 C6 . . . . -48.9(5) no
C7 N1 N2 C11 . . . . -77.4(5) no
C9 N1 C7 C6 . . . . 153.4(4) no
N2 N1 C9 O1A . . . . -9.6(14) no
C7 N1 C9 O1A . . . . 148.6(13) no
N2 N1 C9 C8A . . . . 174.1(6) no
C7 N1 C9 C8A . . . . -27.8(8) no
N2 N1 C7 S1A . . . . -167.9(4) no
N1 N2 C11 C12 . . . . -172.1(3) no
N1 N2 C11 O2 . . . . 8.2(6) no
C15 N3 C16 C12 . . . . 0.3(6) no
C16 N3 C15 C14 . . . . 1.7(6) no
C23 N4 C25 O3B . . . . -178.7(8) no
N5 N4 C25 C24B . . . . -176.0(5) no
C23 N4 C25 C24B . . . . -20.5(7) no
N5 N4 C25 O3B . . . . 25.9(10) no
C23 N4 N5 C27 . . . . -85.1(5) no
C25 N4 N5 C27 . . . . 70.3(5) no
C25 N4 C23 C22 . . . . 142.4(4) no
N5 N4 C23 C22 . . . . -61.9(5) no
C25 N4 C23 S2B . . . . 26.0(5) no
N5 N4 C23 S2B . . . . -178.3(4) no
N4 N5 C27 C28 . . . . -173.9(3) no
N4 N5 C27 O4 . . . . 8.5(6) no
C32 N6 C31 C30 . . . . 1.0(6) no
C31 N6 C32 C28 . . . . -0.7(7) no
C6 C1 C2 C3 . . . . -0.9(9) no
C2 C1 C6 C7 . . . . -177.1(5) no
C2 C1 C6 C5 . . . . 1.5(7) no
C1 C2 C3 C4 . . . . 0.0(9) no
C1 C2 C3 Cl1 . . . . 177.5(5) no
C2 C3 C4 C5 . . . . 0.2(8) no
Cl1 C3 C4 C5 . . . . -177.5(4) no
C3 C4 C5 C6 . . . . 0.5(7) no
C4 C5 C6 C7 . . . . 177.5(4) no
C4 C5 C6 C1 . . . . -1.3(6) no
C1 C6 C7 S1A . . . . 76.2(5) no
C1 C6 C7 N1 . . . . -35.1(6) no
C5 C6 C7 S1A . . . . -102.5(5) no
C5 C6 C7 N1 . . . . 146.2(4) no
S1A C8A C9 N1 . . . . 4.6(9) no
S1A C8A C9 O1A . . . . -172.0(12) no
C10A C8A C9 N1 . . . . 127.7(7) no
C10A C8A C9 O1A . . . . -48.9(14) no
N2 C11 C12 C16 . . . . -13.1(5) no
N2 C11 C12 C13 . . . . 166.0(4) no
O2 C11 C12 C13 . . . . -14.3(6) no
O2 C11 C12 C16 . . . . 166.6(4) no
C13 C12 C16 N3 . . . . -1.3(6) no
C11 C12 C16 N3 . . . . 177.9(4) no
C11 C12 C13 C14 . . . . -178.8(4) no
C16 C12 C13 C14 . . . . 0.4(6) no
C12 C13 C14 C15 . . . . 1.4(7) no
C13 C14 C15 N3 . . . . -2.5(7) no
C18 C17 C22 C23 . . . . 176.4(4) no
C18 C17 C22 C21 . . . . 0.5(6) no
C22 C17 C18 C19 . . . . 0.2(7) no
C17 C18 C19 C20 . . . . 0.3(7) no
C17 C18 C19 Cl2 . . . . 179.9(4) no
C18 C19 C20 C21 . . . . -1.5(7) no
Cl2 C19 C20 C21 . . . . 178.9(4) no
C19 C20 C21 C22 . . . . 2.2(7) no
C20 C21 C22 C23 . . . . -177.4(4) no
C20 C21 C22 C17 . . . . -1.7(7) no
C21 C22 C23 N4 . . . . -23.6(6) no
C21 C22 C23 S2B . . . . 87.8(5) no
C17 C22 C23 N4 . . . . 160.7(4) no
C17 C22 C23 S2B . . . . -87.8(5) no
C26B C24B C25 N4 . . . . 122.6(7) no
S2B C24B C25 N4 . . . . 2.8(8) no
C26B C24B C25 O3B . . . . -79.5(12) no
S2B C24B C25 O3B . . . . 160.6(9) no
N5 C27 C28 C29 . . . . 24.8(5) no
O4 C27 C28 C29 . . . . -157.5(4) no
O4 C27 C28 C32 . . . . 19.8(6) no
N5 C27 C28 C32 . . . . -157.9(4) no
C32 C28 C29 C30 . . . . 0.0(6) no
C27 C28 C32 N6 . . . . -177.3(4) no
C27 C28 C29 C30 . . . . 177.3(4) no
C29 C28 C32 N6 . . . . 0.2(7) no
C28 C29 C30 C31 . . . . 0.3(6) no
C29 C30 C31 N6 . . . . -0.8(6) no
