#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/20/2222053.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_2222053
loop_
_publ_author_name
'Mosslemin, Mohammad Hossein'
'Nateghi, Mohammad Reza'
'Sadoughi, Hesamaddin'
'Lamei, Asal'
_publ_section_title
;4-(4-Chlorophenyl)-6-hydroxy-5-(2-thienylcarbonyl)-6-(trifluoromethyl)-3,4,5,6-tetrahydropyrimidin-2(1H)-one
 monohydrate
;
_journal_coeditor_code           HK2682
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1339
_journal_paper_doi               10.1107/S1600536809017097
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H12 Cl F3 N2 O3 S , H2 O'
_chemical_formula_moiety         'C16 H12 Cl F3 N2 O3 S , H2 O'
_chemical_formula_sum            'C16 H14 Cl F3 N2 O4 S'
_chemical_formula_weight         422.81
_chemical_name_systematic
;
4-(4-Chlorophenyl)-6-hydroxy-5-(2-thienylcarbonyl)-6-(trifluoromethyl)-
3,4,5,6-tetrahydropyrimidin-2(1H)-one monohydrate
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ab'
_symmetry_space_group_name_H-M   'P b n 21'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.1156(6)
_cell_length_b                   14.1582(7)
_cell_length_c                   27.6012(17)
_cell_measurement_reflns_used    1879
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.20
_cell_measurement_theta_min      2.35
_cell_volume                     3562.2(4)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            19595
_diffrn_reflns_theta_full        29.2
_diffrn_reflns_theta_max         29.2
_diffrn_reflns_theta_min         2.35
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.388
_exptl_absorpt_correction_T_max  0.9231
_exptl_absorpt_correction_T_min  0.8601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.467
_refine_ls_abs_structure_details 'Flack (1983), 4326 Friedel pairs'
_refine_ls_abs_structure_Flack   0.18(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     511
_refine_ls_number_reflns         9251
_refine_ls_restrained_S_all      1.07
_refine_ls_R_factor_gt           0.0554
_refine_ls_shift/su_max          0.012
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0679P)²+1.8489P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1461
_reflns_number_gt                7478
_reflns_number_total             9251
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2682.cif
_cod_data_source_block           I
_cod_database_code               2222053
_cod_database_fobs_code          2222053
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,1/2+z
1/2+x,1/2-y,1/2+z
1/2-x,1/2+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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.20863(18) 1.18591(11) 0.10132(6) 0.0800(4) Uani d . 1 . .
Cl Cl2 0.71737(17) 0.07620(11) 0.51510(6) 0.0829(5) Uani d . 1 . .
S S1 -0.37400(15) 0.85338(12) 0.12927(6) 0.0797(4) Uani d . 1 . .
S S2 0.13318(16) 0.40572(12) 0.48988(7) 0.0805(4) Uani d . 1 . .
O O1 -0.2355(3) 0.8588(2) 0.22653(14) 0.0540(8) Uani d . 1 . .
O O2 -0.0969(3) 0.71519(19) 0.27993(10) 0.0401(6) Uani d . 1 . .
H H2B -0.086(4) 0.665(3) 0.2992(15) 0.028(10) Uiso d . 1 . .
O O3 0.3549(3) 0.69972(17) 0.28201(10) 0.0414(6) Uani d . 1 . .
O O4 0.2597(3) 0.4046(3) 0.39238(14) 0.0539(8) Uani d . 1 . .
O O5 0.4027(3) 0.54419(17) 0.33543(9) 0.0394(5) Uani d . 1 . .
H H5 0.396(7) 0.604(4) 0.318(2) 0.088(18) Uiso d . 1 . .
O O6 0.8546(3) 0.55885(17) 0.33323(10) 0.0413(6) Uani d . 1 . .
O O7 0.3736(3) 0.9773(2) 0.30044(11) 0.0433(6) Uani d . 1 . .
H H7A 0.459(8) 0.964(4) 0.309(2) 0.09(2) Uiso d . 1 . .
H H7B 0.321(7) 0.993(4) 0.325(2) 0.080(18) Uiso d . 1 . .
O O8 0.8726(3) 0.2819(2) 0.31572(11) 0.0423(6) Uani d . 1 . .
H H8A 0.946(6) 0.278(3) 0.3038(17) 0.045(13) Uiso d . 1 . .
H H8B 0.820(6) 0.283(4) 0.291(2) 0.066(15) Uiso d . 1 . .
N N1 0.1334(3) 0.66639(19) 0.24968(11) 0.0335(6) Uani d . 1 . .
H H1A 0.1546 0.6074 0.247 0.04 Uiso calc R 1 . .
N N2 0.2184(4) 0.8206(2) 0.25512(13) 0.0408(7) Uani d . 1 . .
H H2A 0.291 0.8579 0.2605 0.049 Uiso calc R 1 . .
N N3 0.6328(3) 0.59341(18) 0.36587(10) 0.0314(5) Uani d . 1 . .
H H3A 0.6543 0.6524 0.3679 0.038 Uiso calc R 1 . .
N N4 0.7153(4) 0.43923(19) 0.36029(13) 0.0385(7) Uani d . 1 . .
H H4A 0.7864 0.4015 0.3535 0.046 Uiso calc R 1 . .
F F1 -0.0306(3) 0.61345(17) 0.16413(9) 0.0574(6) Uani d . 1 . .
F F2 -0.2295(3) 0.6369(2) 0.20268(16) 0.0684(9) Uani d . 1 . .
F F3 -0.0748(3) 0.53514(14) 0.22866(10) 0.0553(6) Uani d . 1 . .
F F4 0.4222(3) 0.72493(15) 0.38632(10) 0.0572(6) Uani d . 1 . .
F F5 0.2705(3) 0.6231(2) 0.41348(15) 0.0686(9) Uani d . 1 . .
F F6 0.4700(3) 0.64863(18) 0.45092(9) 0.0618(7) Uani d . 1 . .
C C1 -0.3412(9) 0.8435(4) 0.0706(3) 0.094(2) Uani d . 1 . .
H H1 -0.4133 0.8506 0.047 0.112 Uiso calc R 1 . .
C C2 -0.2010(10) 0.8242(5) 0.0601(2) 0.084(2) Uani d . 1 . .
H H2 -0.1682 0.8161 0.0285 0.1 Uiso calc R 1 . .
C C3 -0.1067(5) 0.8169(3) 0.10026(15) 0.0440(8) Uani d . 1 . .
H H3 -0.0063 0.8051 0.0994 0.053 Uiso calc R 1 . .
C C4 -0.1978(4) 0.8318(3) 0.14442(15) 0.0426(8) Uani d . 1 . .
C C5 -0.1541(4) 0.8292(2) 0.19488(13) 0.0343(7) Uani d . 1 . .
C C6 -0.0040(3) 0.7890(2) 0.20871(12) 0.0286(6) Uani d . 1 . .
H H6 0.0497 0.7749 0.1788 0.034 Uiso calc R 1 . .
C C7 -0.0144(3) 0.6974(2) 0.23879(11) 0.0288(6) Uani d . 1 . .
C C8 -0.0881(4) 0.6194(2) 0.20873(13) 0.0366(7) Uani d . 1 . .
C C9 0.2396(3) 0.7281(3) 0.26401(15) 0.0311(7) Uani d . 1 . .
C C10 0.0830(4) 0.8633(2) 0.23712(12) 0.0314(6) Uani d . 1 . .
H H10 0.0241 0.8855 0.2646 0.038 Uiso calc R 1 . .
C C11 0.1184(3) 0.9461(2) 0.20424(12) 0.0319(6) Uani d . 1 . .
C C12 0.2245(5) 0.9376(3) 0.1683(2) 0.0462(9) Uani d . 1 . .
H H12 0.2777 0.8818 0.1655 0.055 Uiso calc R 1 . .
C C13 0.2516(4) 1.0109(3) 0.13683(18) 0.0466(11) Uani d . 1 . .
H H13 0.3236 1.0052 0.1131 0.056 Uiso calc R 1 . .
C C14 0.1722(4) 1.0921(3) 0.14066(14) 0.0453(8) Uani d . 1 . .
C C15 0.0667(5) 1.1025(3) 0.17562(15) 0.0461(9) Uani d . 1 . .
H H15 0.0139 1.1586 0.178 0.055 Uiso calc R 1 . .
C C16 0.0395(4) 1.0292(2) 0.20716(14) 0.0397(7) Uani d . 1 . .
H H16 -0.0328 1.0358 0.2307 0.048 Uiso calc R 1 . .
C C17 0.1708(9) 0.4116(5) 0.5484(3) 0.088(2) Uani d . 1 . .
H H17 0.0997 0.4045 0.5723 0.105 Uiso calc R 1 . .
C C18 0.3112(9) 0.4273(4) 0.5583(2) 0.0804(18) Uani d . 1 . .
H H18 0.3463 0.4308 0.5899 0.096 Uiso calc R 1 . .
C C19 0.4056(5) 0.4386(3) 0.51657(13) 0.0444(8) Uani d . 1 . .
H H19 0.506 0.4501 0.5167 0.053 Uiso calc R 1 . .
C C20 0.3103(4) 0.4283(3) 0.47414(15) 0.0421(8) Uani d . 1 . .
C C21 0.3463(4) 0.4322(2) 0.42239(14) 0.0365(7) Uani d . 1 . .
C C22 0.4972(3) 0.4722(2) 0.40755(11) 0.0287(6) Uani d . 1 . .
H H22 0.5523 0.4871 0.4371 0.034 Uiso calc R 1 . .
C C23 0.4852(3) 0.5625(2) 0.37684(11) 0.0285(6) Uani d . 1 . .
C C24 0.4120(4) 0.6412(2) 0.40686(14) 0.0386(7) Uani d . 1 . .
C C25 0.7380(4) 0.5309(2) 0.35238(16) 0.0331(8) Uani d . 1 . .
C C26 0.5819(3) 0.3969(2) 0.37927(12) 0.0307(6) Uani d . 1 . .
H H26 0.5215 0.3742 0.3523 0.037 Uiso calc R 1 . .
C C27 0.6181(3) 0.3148(2) 0.41269(12) 0.0307(6) Uani d . 1 . .
C C28 0.5391(4) 0.2319(2) 0.40975(14) 0.0401(7) Uani d . 1 . .
H H28 0.4665 0.2253 0.3863 0.048 Uiso calc R 1 . .
C C29 0.5675(4) 0.1575(3) 0.44180(17) 0.0499(9) Uani d . 1 . .
H H29 0.5138 0.1017 0.4402 0.06 Uiso calc R 1 . .
C C30 0.6760(4) 0.1689(3) 0.47547(15) 0.0492(10) Uani d . 1 . .
C C31 0.7576(5) 0.2514(3) 0.4788(2) 0.0515(12) Uani d . 1 . .
H H31 0.8306 0.2575 0.5021 0.062 Uiso calc R 1 . .
C C32 0.7287(4) 0.3237(3) 0.44722(16) 0.0398(8) Uani d . 1 . .
H H32 0.7833 0.3791 0.4488 0.048 Uiso calc R 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 0 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
C1 S1 C4 . . 93.2(3) ?
C17 S2 C20 . . 92.5(3) ?
C7 O2 H2B . . 107(3) ?
C23 O5 H5 . . 106(4) ?
H7A O7 H7B . . 110(6) ?
H8A O8 H8B . . 99(5) ?
C7 N1 H1A . . 119.1 ?
C9 N1 C7 . . 121.8(3) ?
C9 N1 H1A . . 119.1 ?
C9 N2 C10 . . 125.9(3) ?
C9 N2 H2A . . 117.1 ?
C10 N2 H2A . . 117.1 ?
C23 N3 H3A . . 119.4 ?
C25 N3 C23 . . 121.1(3) ?
C25 N3 H3A . . 119.4 ?
C25 N4 C26 . . 126.2(3) ?
C25 N4 H4A . . 116.9 ?
C26 N4 H4A . . 116.9 ?
C2 C1 S1 . . 113.7(4) ?
C2 C1 H1 . . 123.2 ?
S1 C1 H1 . . 123.2 ?
C1 C2 C3 . . 115.4(6) ?
C1 C2 H2 . . 122.3 ?
C3 C2 H2 . . 122.3 ?
C2 C3 C4 . . 107.1(4) ?
C2 C3 H3 . . 126.5 ?
C4 C3 H3 . . 126.5 ?
C5 C4 C3 . . 129.0(3) ?
C5 C4 S1 . . 120.3(3) ?
C3 C4 S1 . . 110.7(3) ?
O1 C5 C4 . . 120.8(3) ?
O1 C5 C6 . . 119.5(3) ?
C4 C5 C6 . . 119.7(3) ?
C5 C6 C10 . . 109.6(2) ?
C5 C6 C7 . . 113.1(2) ?
C10 C6 C7 . . 109.5(2) ?
C5 C6 H6 . . 108.2 ?
C10 C6 H6 . . 108.2 ?
C7 C6 H6 . . 108.2 ?
O2 C7 N1 . . 112.9(3) ?
O2 C7 C8 . . 109.6(3) ?
N1 C7 C8 . . 107.5(2) ?
O2 C7 C6 . . 108.8(2) ?
N1 C7 C6 . . 108.0(2) ?
C8 C7 C6 . . 109.9(2) ?
F3 C8 F2 . . 108.2(3) ?
F3 C8 F1 . . 106.9(3) ?
F2 C8 F1 . . 106.0(3) ?
F3 C8 C7 . . 112.7(3) ?
F2 C8 C7 . . 111.0(3) ?
F1 C8 C7 . . 111.7(3) ?
O3 C9 N2 . . 120.9(3) ?
O3 C9 N1 . . 121.0(3) ?
N2 C9 N1 . . 118.0(3) ?
N2 C10 C11 . . 110.1(3) ?
N2 C10 C6 . . 109.1(2) ?
C11 C10 C6 . . 109.5(3) ?
N2 C10 H10 . . 109.4 ?
C11 C10 H10 . . 109.4 ?
C6 C10 H10 . . 109.4 ?
C16 C11 C12 . . 118.5(3) ?
C16 C11 C10 . . 120.8(3) ?
C12 C11 C10 . . 120.5(3) ?
C13 C12 C11 . . 120.6(4) ?
C13 C12 H12 . . 119.7 ?
C11 C12 H12 . . 119.7 ?
C14 C13 C12 . . 119.5(4) ?
C14 C13 H13 . . 120.3 ?
C12 C13 H13 . . 120.3 ?
C13 C14 C15 . . 121.2(4) ?
C13 C14 Cl1 . . 119.5(3) ?
C15 C14 Cl1 . . 119.3(3) ?
C14 C15 C16 . . 119.4(3) ?
C14 C15 H15 . . 120.3 ?
C16 C15 H15 . . 120.3 ?
C15 C16 C11 . . 120.8(3) ?
C15 C16 H16 . . 119.6 ?
C11 C16 H16 . . 119.6 ?
C18 C17 S2 . . 114.3(4) ?
C18 C17 H17 . . 122.9 ?
S2 C17 H17 . . 122.9 ?
C17 C18 C19 . . 115.2(5) ?
C17 C18 H18 . . 122.4 ?
C19 C18 H18 . . 122.4 ?
C18 C19 C20 . . 105.9(4) ?
C18 C19 H19 . . 127.1 ?
C20 C19 H19 . . 127.1 ?
C19 C20 C21 . . 130.0(3) ?
C19 C20 S2 . . 112.1(3) ?
C21 C20 S2 . . 117.9(3) ?
O4 C21 C20 . . 120.6(3) ?
O4 C21 C22 . . 121.3(3) ?
C20 C21 C22 . . 118.2(3) ?
C26 C22 C23 . . 109.5(2) ?
C26 C22 C21 . . 109.3(2) ?
C23 C22 C21 . . 112.8(2) ?
C26 C22 H22 . . 108.4 ?
C23 C22 H22 . . 108.4 ?
C21 C22 H22 . . 108.4 ?
O5 C23 N3 . . 112.8(3) ?
O5 C23 C22 . . 109.6(2) ?
N3 C23 C22 . . 107.5(2) ?
O5 C23 C24 . . 110.0(3) ?
N3 C23 C24 . . 107.3(2) ?
C22 C23 C24 . . 109.6(2) ?
F4 C24 F5 . . 107.6(3) ?
F4 C24 F6 . . 107.1(3) ?
F5 C24 F6 . . 106.0(3) ?
F4 C24 C23 . . 112.9(3) ?
F5 C24 C23 . . 110.8(3) ?
F6 C24 C23 . . 112.1(3) ?
O6 C25 N4 . . 120.6(3) ?
O6 C25 N3 . . 120.6(3) ?
N4 C25 N3 . . 118.8(3) ?
N4 C26 C27 . . 110.6(3) ?
N4 C26 C22 . . 108.6(2) ?
C27 C26 C22 . . 109.4(3) ?
N4 C26 H26 . . 109.4 ?
C27 C26 H26 . . 109.4 ?
C22 C26 H26 . . 109.4 ?
C28 C27 C32 . . 119.6(3) ?
C28 C27 C26 . . 120.1(3) ?
C32 C27 C26 . . 120.2(3) ?
C27 C28 C29 . . 120.5(4) ?
C27 C28 H28 . . 119.8 ?
C29 C28 H28 . . 119.8 ?
C30 C29 C28 . . 118.3(4) ?
C30 C29 H29 . . 120.8 ?
C28 C29 H29 . . 120.8 ?
C29 C30 C31 . . 122.2(4) ?
C29 C30 Cl2 . . 119.5(3) ?
C31 C30 Cl2 . . 118.3(4) ?
C32 C31 C30 . . 118.9(4) ?
C32 C31 H31 . . 120.6 ?
C30 C31 H31 . . 120.6 ?
C31 C32 C27 . . 120.5(4) ?
C31 C32 H32 . . 119.7 ?
C27 C32 H32 . . 119.7 ?
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
O2 H2B . 0.89(4) ?
O5 H5 . 0.99(6) ?
O7 H7A . 0.84(7) ?
O7 H7B . 0.87(7) ?
O8 H8A . 0.75(5) ?
O8 H8B . 0.84(6) ?
N1 H1A . 0.86 ?
N2 H2A . 0.86 ?
N3 H3A . 0.86 ?
N4 H4A . 0.86 ?
C1 C2 . 1.338(11) ?
C1 S1 . 1.653(8) ?
C1 H1 . 0.93 ?
C2 C3 . 1.407(7) ?
C2 H2 . 0.93 ?
C3 C4 . 1.490(6) ?
C3 H3 . 0.93 ?
C4 C5 . 1.449(5) ?
C4 S1 . 1.688(4) ?
C5 O1 . 1.221(5) ?
C5 C6 . 1.530(4) ?
C6 C10 . 1.533(4) ?
C6 C7 . 1.543(4) ?
C6 H6 . 0.98 ?
C7 O2 . 1.385(4) ?
C7 N1 . 1.448(4) ?
C7 C8 . 1.536(4) ?
C8 F3 . 1.319(4) ?
C8 F2 . 1.323(4) ?
C8 F1 . 1.340(4) ?
C9 O3 . 1.230(4) ?
C9 N2 . 1.347(4) ?
C9 N1 . 1.363(4) ?
C10 N2 . 1.461(4) ?
C10 C11 . 1.517(4) ?
C10 H10 . 0.98 ?
C11 C16 . 1.382(5) ?
C11 C12 . 1.391(5) ?
C12 C13 . 1.376(6) ?
C12 H12 . 0.93 ?
C13 C14 . 1.363(6) ?
C13 H13 . 0.93 ?
C14 C15 . 1.370(6) ?
C14 Cl1 . 1.747(4) ?
C15 C16 . 1.377(5) ?
C15 H15 . 0.93 ?
C16 H16 . 0.93 ?
C17 C18 . 1.328(11) ?
C17 S2 . 1.652(8) ?
C17 H17 . 0.93 ?
C18 C19 . 1.448(7) ?
C18 H18 . 0.93 ?
C19 C20 . 1.465(6) ?
C19 H19 . 0.93 ?
C20 C21 . 1.467(5) ?
C20 S2 . 1.703(4) ?
C21 O4 . 1.209(5) ?
C21 C22 . 1.542(4) ?
C22 C26 . 1.530(4) ?
C22 C23 . 1.538(4) ?
C22 H22 . 0.98 ?
C23 O5 . 1.393(4) ?
C23 N3 . 1.447(4) ?
C23 C24 . 1.541(4) ?
C24 F4 . 1.317(4) ?
C24 F5 . 1.328(4) ?
C24 F6 . 1.330(5) ?
C25 O6 . 1.252(4) ?
C25 N4 . 1.332(4) ?
C25 N3 . 1.357(4) ?
C26 N4 . 1.453(4) ?
C26 C27 . 1.520(4) ?
C26 H26 . 0.98 ?
C27 C28 . 1.380(5) ?
C27 C32 . 1.393(5) ?
C28 C29 . 1.399(5) ?
C28 H28 . 0.93 ?
C29 C30 . 1.367(6) ?
C29 H29 . 0.93 ?
C30 C31 . 1.388(7) ?
C30 Cl2 . 1.750(4) ?
C31 C32 . 1.370(6) ?
C31 H31 . 0.93 ?
C32 H32 . 0.93 ?
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 F3 . 0.86 2.38 2.719(4) 104 yes
N1 H1A O7 4_545 0.86 2.37 3.022(4) 132 yes
N2 H2A O7 . 0.86 2.15 2.914(4) 147 yes
O2 H2B O6 1_455 0.89(4) 1.85(4) 2.694(4) 156(3) yes
N3 H3A F4 . 0.86 2.41 2.733(4) 103 yes
N3 H3A O8 4_655 0.86 2.34 3.007(4) 134 yes
N4 H4A O8 . 0.86 2.14 2.921(4) 151 yes
O5 H5 O3 . 0.98(6) 1.72(6) 2.686(4) 169(6) yes
O7 H7A O6 4_655 0.84(7) 2.27(7) 2.879(4) 130(5) yes
O7 H7B O4 4_555 0.86(6) 2.36(6) 2.996(5) 131(5) yes
O7 H7B O5 4_555 0.86(6) 2.18(6) 2.859(4) 135(5) yes
O8 H8A O3 4_645 0.75(5) 2.21(5) 2.897(4) 153(4) yes
O8 H8B O1 4_545 0.83(5) 2.22(6) 2.968(5) 150(5) yes
O8 H8B O2 4_545 0.83(5) 2.27(6) 2.861(4) 128(5) 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
S1 C1 C2 C3 . . . . -0.8(8) ?
C1 C2 C3 C4 . . . . 1.3(7) ?
C2 C3 C4 C5 . . . . 178.4(5) ?
C2 C3 C4 S1 . . . . -1.2(5) ?
C3 C4 C5 O1 . . . . 167.1(4) ?
S1 C4 C5 O1 . . . . -13.2(5) ?
C3 C4 C5 C6 . . . . -12.8(6) ?
S1 C4 C5 C6 . . . . 166.8(3) ?
O1 C5 C6 C10 . . . . -56.5(4) ?
C4 C5 C6 C10 . . . . 123.4(3) ?
O1 C5 C6 C7 . . . . 65.9(4) ?
C4 C5 C6 C7 . . . . -114.1(3) ?
C5 C6 C7 O2 . . . . -57.0(3) ?
C10 C6 C7 O2 . . . . 65.5(3) ?
C5 C6 C7 N1 . . . . -179.9(3) ?
C10 C6 C7 N1 . . . . -57.4(3) ?
C5 C6 C7 C8 . . . . 63.1(3) ?
C10 C6 C7 C8 . . . . -174.5(3) ?
O2 C7 C8 F3 . . . . -72.8(4) ?
N1 C7 C8 F3 . . . . 50.3(4) ?
C6 C7 C8 F3 . . . . 167.7(3) ?
O2 C7 C8 F2 . . . . 48.7(4) ?
N1 C7 C8 F2 . . . . 171.8(3) ?
C6 C7 C8 F2 . . . . -70.8(4) ?
O2 C7 C8 F1 . . . . 166.9(3) ?
N1 C7 C8 F1 . . . . -70.0(3) ?
C6 C7 C8 F1 . . . . 47.3(3) ?
C5 C6 C10 N2 . . . . 173.3(3) ?
C7 C6 C10 N2 . . . . 48.7(3) ?
C5 C6 C10 C11 . . . . -66.2(3) ?
C7 C6 C10 C11 . . . . 169.2(3) ?
N2 C10 C11 C16 . . . . -137.7(3) ?
C6 C10 C11 C16 . . . . 102.4(4) ?
N2 C10 C11 C12 . . . . 46.7(4) ?
C6 C10 C11 C12 . . . . -73.2(4) ?
C16 C11 C12 C13 . . . . 1.0(6) ?
C10 C11 C12 C13 . . . . 176.7(4) ?
C11 C12 C13 C14 . . . . -0.9(7) ?
C12 C13 C14 C15 . . . . 0.7(7) ?
C12 C13 C14 Cl1 . . . . 179.0(4) ?
C13 C14 C15 C16 . . . . -0.6(6) ?
Cl1 C14 C15 C16 . . . . -179.0(3) ?
C14 C15 C16 C11 . . . . 0.7(6) ?
C12 C11 C16 C15 . . . . -0.9(6) ?
C10 C11 C16 C15 . . . . -176.6(3) ?
S2 C17 C18 C19 . . . . 1.3(7) ?
C17 C18 C19 C20 . . . . -0.1(6) ?
C18 C19 C20 C21 . . . . -179.4(4) ?
C18 C19 C20 S2 . . . . -1.1(4) ?
C19 C20 C21 O4 . . . . 165.8(4) ?
S2 C20 C21 O4 . . . . -12.3(5) ?
C19 C20 C21 C22 . . . . -14.0(6) ?
S2 C20 C21 C22 . . . . 167.8(2) ?
O4 C21 C22 C26 . . . . -58.9(4) ?
C20 C21 C22 C26 . . . . 120.9(3) ?
O4 C21 C22 C23 . . . . 63.1(4) ?
C20 C21 C22 C23 . . . . -117.0(3) ?
C26 C22 C23 O5 . . . . 64.1(3) ?
C21 C22 C23 O5 . . . . -57.8(3) ?
C26 C22 C23 N3 . . . . -58.8(3) ?
C21 C22 C23 N3 . . . . 179.3(3) ?
C26 C22 C23 C24 . . . . -175.1(3) ?
C21 C22 C23 C24 . . . . 63.0(3) ?
O5 C23 C24 F4 . . . . -71.1(3) ?
N3 C23 C24 F4 . . . . 51.9(4) ?
C22 C23 C24 F4 . . . . 168.3(3) ?
O5 C23 C24 F5 . . . . 49.6(4) ?
N3 C23 C24 F5 . . . . 172.6(3) ?
C22 C23 C24 F5 . . . . -71.0(4) ?
O5 C23 C24 F6 . . . . 167.8(3) ?
N3 C23 C24 F6 . . . . -69.2(3) ?
C22 C23 C24 F6 . . . . 47.2(4) ?
C23 C22 C26 N4 . . . . 48.8(3) ?
C21 C22 C26 N4 . . . . 172.8(3) ?
C23 C22 C26 C27 . . . . 169.7(2) ?
C21 C22 C26 C27 . . . . -66.3(3) ?
N4 C26 C27 C28 . . . . -136.7(3) ?
C22 C26 C27 C28 . . . . 103.7(4) ?
N4 C26 C27 C32 . . . . 44.8(4) ?
C22 C26 C27 C32 . . . . -74.8(4) ?
C32 C27 C28 C29 . . . . 1.3(6) ?
C26 C27 C28 C29 . . . . -177.2(3) ?
C27 C28 C29 C30 . . . . -0.7(6) ?
C28 C29 C30 C31 . . . . 0.2(6) ?
C28 C29 C30 Cl2 . . . . -178.4(3) ?
C29 C30 C31 C32 . . . . -0.2(7) ?
Cl2 C30 C31 C32 . . . . 178.4(3) ?
C30 C31 C32 C27 . . . . 0.8(7) ?
C28 C27 C32 C31 . . . . -1.3(6) ?
C26 C27 C32 C31 . . . . 177.2(4) ?
O3 C9 N1 C7 . . . . 165.8(4) ?
N2 C9 N1 C7 . . . . -18.2(5) ?
O2 C7 N1 C9 . . . . -77.2(4) ?
C8 C7 N1 C9 . . . . 161.8(3) ?
C6 C7 N1 C9 . . . . 43.2(4) ?
O3 C9 N2 C10 . . . . -175.4(4) ?
N1 C9 N2 C10 . . . . 8.6(6) ?
C11 C10 N2 C9 . . . . -145.7(4) ?
C6 C10 N2 C9 . . . . -25.5(5) ?
O6 C25 N3 C23 . . . . 164.7(4) ?
N4 C25 N3 C23 . . . . -15.9(6) ?
O5 C23 N3 C25 . . . . -77.9(4) ?
C22 C23 N3 C25 . . . . 43.0(4) ?
C24 C23 N3 C25 . . . . 160.8(3) ?
O6 C25 N4 C26 . . . . -175.8(4) ?
N3 C25 N4 C26 . . . . 4.8(7) ?
C27 C26 N4 C25 . . . . -142.9(4) ?
C22 C26 N4 C25 . . . . -22.8(5) ?
C2 C1 S1 C4 . . . . 0.0(6) ?
C5 C4 S1 C1 . . . . -179.0(4) ?
C3 C4 S1 C1 . . . . 0.8(4) ?
C18 C17 S2 C20 . . . . -1.7(5) ?
C19 C20 S2 C17 . . . . 1.6(4) ?
C21 C20 S2 C17 . . . . -179.9(4) ?
