#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/14/2221447.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_2221447
loop_
_publ_author_name
'Hussain, Abid'
'Hameed, Shahid'
'Stoeckli-Evans, Helen'
_publ_section_title
1-(4-Chlorophenylsulfonyl)-5-(4-fluorophenyl)-5-methylimidazolidine-2,4-dione
_journal_coeditor_code           NC2138
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o858
_journal_page_last               o859
_journal_paper_doi               10.1107/S160053680901037X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H12 Cl F N2 O4 S'
_chemical_formula_moiety         'C16 H12 Cl F N2 O4 S'
_chemical_formula_sum            'C16 H12 Cl F N2 O4 S'
_chemical_formula_weight         382.79
_chemical_name_systematic
;
1-(4-Chlorophenylsulfonyl)-5-(4-fluorophenyl)-5-methylimidazolidine-2,4-dione
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                92.098(6)
_cell_angle_beta                 93.630(6)
_cell_angle_gamma                103.056(6)
_cell_formula_units_Z            4
_cell_length_a                   9.6959(7)
_cell_length_b                   10.0066(7)
_cell_length_c                   16.6269(13)
_cell_measurement_reflns_used    20500
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.49
_cell_measurement_theta_min      2.09
_cell_volume                     1566.2(2)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2006)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2006)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2006)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Stoe IPDS-2'
_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  0.0415
_diffrn_reflns_av_sigmaI/netI    0.0427
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            30542
_diffrn_reflns_theta_full        29.27
_diffrn_reflns_theta_max         29.27
_diffrn_reflns_theta_min         2.09
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.414
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.641
_refine_ls_extinction_coef       0.0070(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.893
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     462
_refine_ls_number_reflns         8438
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.893
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0373
_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)+(0.0594P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.0953
_reflns_number_gt                5836
_reflns_number_total             8438
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            nc2138.cif
_cod_data_source_block           I
_cod_database_code               2221447
_cod_database_fobs_code          2221447
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 0.91764(7) -0.33306(8) 0.44481(3) 0.0678(2) Uani . . 1.000
S S1 1.07493(4) 0.03707(4) 0.15675(2) 0.02160(10) Uani . . 1.000
F F1 0.74943(12) 0.11810(12) 0.46455(6) 0.0435(4) Uani . . 1.000
O O1 0.88878(13) -0.18444(11) 0.04068(7) 0.0292(3) Uani . . 1.000
O O2 0.57120(12) 0.08199(11) 0.07970(6) 0.0266(3) Uani . . 1.000
O O3 1.12161(12) 0.17630(11) 0.18656(8) 0.0317(3) Uani . . 1.000
O O4 1.15471(12) -0.02016(12) 0.10155(7) 0.0306(3) Uani . . 1.000
N N1 0.91377(13) 0.02536(12) 0.11173(7) 0.0188(3) Uani . . 1.000
N N2 0.70525(14) -0.07265(13) 0.04699(7) 0.0217(4) Uani . . 1.000
C C1 1.04515(16) -0.06802(16) 0.23943(9) 0.0239(4) Uani . . 1.000
C C2 1.06304(19) -0.00804(19) 0.31679(10) 0.0324(5) Uani . . 1.000
C C3 1.0280(2) -0.0905(2) 0.38108(10) 0.0412(6) Uani . . 1.000
C C4 0.9731(2) -0.2300(2) 0.36571(11) 0.0399(6) Uani . . 1.000
C C5 0.95939(19) -0.29070(19) 0.28916(11) 0.0350(5) Uani . . 1.000
C C6 0.99744(17) -0.20954(16) 0.22461(10) 0.0271(5) Uani . . 1.000
C C7 0.84130(17) -0.08949(14) 0.06303(8) 0.0211(4) Uani . . 1.000
C C8 0.68087(16) 0.04368(14) 0.08337(8) 0.0192(4) Uani . . 1.000
C C9 0.81941(15) 0.11962(13) 0.13079(8) 0.0175(4) Uani . . 1.000
C C10 0.86819(16) 0.25816(14) 0.09386(9) 0.0227(4) Uani . . 1.000
C C11 0.79666(15) 0.12483(14) 0.22069(8) 0.0180(4) Uani . . 1.000
C C12 0.84186(16) 0.24448(15) 0.26969(9) 0.0230(4) Uani . . 1.000
C C13 0.82563(18) 0.24327(17) 0.35230(9) 0.0287(5) Uani . . 1.000
C C14 0.76299(18) 0.12121(18) 0.38395(9) 0.0282(5) Uani . . 1.000
C C15 0.71357(17) 0.00078(16) 0.33735(9) 0.0264(4) Uani . . 1.000
C C16 0.73163(16) 0.00364(15) 0.25529(8) 0.0221(4) Uani . . 1.000
Cl Cl2 0.40511(6) 0.12790(6) 0.43991(3) 0.0533(2) Uani . . 1.000
S S2 0.58277(4) 0.54282(4) 0.17383(2) 0.02380(10) Uani . . 1.000
F F2 0.23250(13) 0.58675(13) 0.47233(6) 0.0462(4) Uani . . 1.000
O O5 0.41852(14) 0.33765(12) 0.04019(7) 0.0323(4) Uani . . 1.000
O O6 0.08075(12) 0.57818(11) 0.08571(6) 0.0268(3) Uani . . 1.000
O O7 0.62142(12) 0.67806(11) 0.21087(8) 0.0329(4) Uani . . 1.000
O O8 0.67356(13) 0.49688(12) 0.12089(8) 0.0349(4) Uani . . 1.000
N N3 0.42774(14) 0.53320(12) 0.12274(7) 0.0207(4) Uani . . 1.000
N N4 0.22860(15) 0.43999(13) 0.04734(7) 0.0245(4) Uani . . 1.000
C C17 0.54287(17) 0.42502(15) 0.25006(9) 0.0246(4) Uani . . 1.000
C C18 0.55335(19) 0.47308(18) 0.32980(10) 0.0314(5) Uani . . 1.000
C C19 0.5129(2) 0.3808(2) 0.38883(10) 0.0366(6) Uani . . 1.000
C C20 0.46166(19) 0.24306(19) 0.36642(10) 0.0340(5) Uani . . 1.000
C C21 0.45376(18) 0.19449(17) 0.28735(10) 0.0313(5) Uani . . 1.000
C C22 0.49622(17) 0.28577(15) 0.22782(9) 0.0258(4) Uani . . 1.000
C C23 0.36440(17) 0.42562(15) 0.06618(8) 0.0234(4) Uani . . 1.000
C C24 0.19359(16) 0.54614(14) 0.08942(8) 0.0203(4) Uani . . 1.000
C C25 0.32640(15) 0.62082(13) 0.14231(8) 0.0181(4) Uani . . 1.000
C C26 0.37432(17) 0.76406(14) 0.11053(9) 0.0235(4) Uani . . 1.000
C C27 0.29616(15) 0.61719(14) 0.23119(8) 0.0188(4) Uani . . 1.000
C C28 0.34294(17) 0.73075(15) 0.28478(9) 0.0250(4) Uani . . 1.000
C C29 0.32074(18) 0.72166(17) 0.36611(10) 0.0312(5) Uani . . 1.000
C C30 0.25095(18) 0.59752(18) 0.39255(9) 0.0300(5) Uani . . 1.000
C C31 0.19982(18) 0.48331(17) 0.34161(9) 0.0280(5) Uani . . 1.000
C C32 0.22340(16) 0.49359(15) 0.26027(9) 0.0226(4) Uani . . 1.000
H H2 1.09880 0.08820 0.32580 0.0390 Uiso calc R 1.000
H H2N 0.646(2) -0.124(2) 0.0142(12) 0.037(5) Uiso . . 1.000
H H3 1.04140 -0.05190 0.43480 0.0490 Uiso calc R 1.000
H H5 0.92420 -0.38710 0.28060 0.0420 Uiso calc R 1.000
H H6 0.99110 -0.24960 0.17140 0.0330 Uiso calc R 1.000
H H10A 0.88320 0.24360 0.03680 0.0340 Uiso calc R 1.000
H H10B 0.95730 0.30860 0.12250 0.0340 Uiso calc R 1.000
H H10C 0.79550 0.31140 0.09860 0.0340 Uiso calc R 1.000
H H12 0.88430 0.32790 0.24650 0.0280 Uiso calc R 1.000
H H13 0.85700 0.32470 0.38590 0.0340 Uiso calc R 1.000
H H15 0.66860 -0.08150 0.36080 0.0320 Uiso calc R 1.000
H H16 0.69920 -0.07820 0.22210 0.0260 Uiso calc R 1.000
H H4N 0.170(2) 0.3855(19) 0.0117(11) 0.031(5) Uiso . . 1.000
H H18 0.58780 0.56820 0.34390 0.0380 Uiso calc R 1.000
H H19 0.52030 0.41170 0.44400 0.0440 Uiso calc R 1.000
H H21 0.41950 0.09920 0.27360 0.0370 Uiso calc R 1.000
H H22 0.49350 0.25380 0.17310 0.0310 Uiso calc R 1.000
H H26A 0.38990 0.75590 0.05310 0.0350 Uiso calc R 1.000
H H26B 0.46290 0.81250 0.14050 0.0350 Uiso calc R 1.000
H H26C 0.30080 0.81560 0.11770 0.0350 Uiso calc R 1.000
H H28 0.39080 0.81570 0.26540 0.0300 Uiso calc R 1.000
H H29 0.35290 0.79930 0.40270 0.0370 Uiso calc R 1.000
H H31 0.14980 0.39970 0.36150 0.0340 Uiso calc R 1.000
H H32 0.18970 0.41570 0.22400 0.0270 Uiso calc R 1.000
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'
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'
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O3 S1 O4 . . . 120.54(7) no
O3 S1 N1 . . . 105.32(7) no
O3 S1 C1 . . . 108.55(8) no
O4 S1 N1 . . . 107.44(7) no
O4 S1 C1 . . . 109.31(7) no
N1 S1 C1 . . . 104.49(7) no
O8 S2 N3 . . . 107.85(7) no
O8 S2 C17 . . . 109.35(8) no
N3 S2 C17 . . . 104.29(7) no
O7 S2 C17 . . . 108.38(7) no
O7 S2 O8 . . . 120.43(7) no
O7 S2 N3 . . . 105.34(7) no
C7 N1 C9 . . . 111.78(12) no
S1 N1 C9 . . . 124.37(9) no
S1 N1 C7 . . . 122.81(11) no
C7 N2 C8 . . . 113.69(12) no
C8 N2 H2N . . . 122.9(14) no
C7 N2 H2N . . . 123.1(14) no
S2 N3 C25 . . . 124.18(9) no
S2 N3 C23 . . . 123.49(11) no
C23 N3 C25 . . . 111.33(12) no
C23 N4 C24 . . . 114.09(12) no
C24 N4 H4N . . . 123.3(13) no
C23 N4 H4N . . . 122.6(13) no
S1 C1 C6 . . . 118.72(12) no
C2 C1 C6 . . . 121.81(15) no
S1 C1 C2 . . . 119.40(13) no
C1 C2 C3 . . . 119.02(17) no
C2 C3 C4 . . . 118.98(16) no
Cl1 C4 C3 . . . 119.61(14) no
Cl1 C4 C5 . . . 118.26(15) no
C3 C4 C5 . . . 122.13(17) no
C4 C5 C6 . . . 119.27(17) no
C1 C6 C5 . . . 118.64(15) no
O1 C7 N1 . . . 126.44(15) no
N1 C7 N2 . . . 106.47(12) no
O1 C7 N2 . . . 127.08(14) no
N2 C8 C9 . . . 107.77(13) no
O2 C8 C9 . . . 125.18(13) no
O2 C8 N2 . . . 127.05(14) no
C10 C9 C11 . . . 115.85(11) no
N1 C9 C8 . . . 100.25(10) no
N1 C9 C10 . . . 111.26(12) no
C8 C9 C10 . . . 107.59(11) no
C8 C9 C11 . . . 109.55(12) no
N1 C9 C11 . . . 111.12(11) no
C12 C11 C16 . . . 118.98(13) no
C9 C11 C16 . . . 118.47(12) no
C9 C11 C12 . . . 122.52(12) no
C11 C12 C13 . . . 120.71(14) no
C12 C13 C14 . . . 118.31(14) no
F1 C14 C15 . . . 118.21(15) no
C13 C14 C15 . . . 122.95(14) no
F1 C14 C13 . . . 118.84(15) no
C14 C15 C16 . . . 117.94(14) no
C11 C16 C15 . . . 121.08(13) no
C3 C2 H2 . . . 120.00 no
C1 C2 H2 . . . 121.00 no
C2 C3 H3 . . . 120.00 no
C4 C3 H3 . . . 121.00 no
C4 C5 H5 . . . 120.00 no
C6 C5 H5 . . . 120.00 no
C1 C6 H6 . . . 121.00 no
C5 C6 H6 . . . 121.00 no
C9 C10 H10B . . . 109.00 no
H10A C10 H10C . . . 109.00 no
H10B C10 H10C . . . 109.00 no
C9 C10 H10A . . . 109.00 no
C9 C10 H10C . . . 109.00 no
H10A C10 H10B . . . 109.00 no
C13 C12 H12 . . . 120.00 no
C11 C12 H12 . . . 120.00 no
C14 C13 H13 . . . 121.00 no
C12 C13 H13 . . . 121.00 no
C16 C15 H15 . . . 121.00 no
C14 C15 H15 . . . 121.00 no
C15 C16 H16 . . . 119.00 no
C11 C16 H16 . . . 119.00 no
S2 C17 C18 . . . 119.53(12) no
C18 C17 C22 . . . 121.65(14) no
S2 C17 C22 . . . 118.78(11) no
C17 C18 C19 . . . 119.20(16) no
C18 C19 C20 . . . 119.16(16) no
Cl2 C20 C21 . . . 118.94(14) no
Cl2 C20 C19 . . . 119.28(13) no
C19 C20 C21 . . . 121.79(16) no
C20 C21 C22 . . . 119.53(15) no
C17 C22 C21 . . . 118.62(14) no
N3 C23 N4 . . . 106.55(13) no
O5 C23 N3 . . . 126.46(15) no
O5 C23 N4 . . . 126.98(14) no
O6 C24 N4 . . . 127.18(14) no
O6 C24 C25 . . . 125.42(13) no
N4 C24 C25 . . . 107.39(13) no
N3 C25 C24 . . . 100.55(10) no
C24 C25 C26 . . . 107.20(11) no
C24 C25 C27 . . . 110.25(12) no
C26 C25 C27 . . . 115.47(11) no
N3 C25 C26 . . . 110.75(12) no
N3 C25 C27 . . . 111.50(11) no
C28 C27 C32 . . . 118.95(13) no
C25 C27 C28 . . . 122.38(12) no
C25 C27 C32 . . . 118.63(12) no
C27 C28 C29 . . . 120.87(14) no
C28 C29 C30 . . . 118.37(15) no
F2 C30 C31 . . . 118.41(15) no
F2 C30 C29 . . . 118.72(15) no
C29 C30 C31 . . . 122.88(15) no
C30 C31 C32 . . . 118.17(15) no
C27 C32 C31 . . . 120.74(14) no
C17 C18 H18 . . . 120.00 no
C19 C18 H18 . . . 120.00 no
C18 C19 H19 . . . 120.00 no
C20 C19 H19 . . . 120.00 no
C20 C21 H21 . . . 120.00 no
C22 C21 H21 . . . 120.00 no
C17 C22 H22 . . . 121.00 no
C21 C22 H22 . . . 121.00 no
C25 C26 H26A . . . 109.00 no
C25 C26 H26B . . . 109.00 no
C25 C26 H26C . . . 109.00 no
H26A C26 H26B . . . 110.00 no
H26A C26 H26C . . . 109.00 no
H26B C26 H26C . . . 109.00 no
C27 C28 H28 . . . 120.00 no
C29 C28 H28 . . . 120.00 no
C28 C29 H29 . . . 121.00 no
C30 C29 H29 . . . 121.00 no
C30 C31 H31 . . . 121.00 no
C32 C31 H31 . . . 121.00 no
C27 C32 H32 . . . 120.00 no
C31 C32 H32 . . . 120.00 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 C4 . . 1.738(2) no
Cl2 C20 . . 1.7390(18) no
S1 O4 . . 1.4214(12) no
S1 N1 . . 1.6669(13) no
S1 C1 . . 1.7601(16) no
S1 O3 . . 1.4240(12) no
S2 O7 . . 1.4254(12) no
S2 O8 . . 1.4186(14) no
S2 C17 . . 1.7638(15) no
S2 N3 . . 1.6605(14) no
F1 C14 . . 1.3556(18) no
F2 C30 . . 1.3546(18) no
O1 C7 . . 1.2026(19) no
O2 C8 . . 1.208(2) no
O5 C23 . . 1.203(2) no
O6 C24 . . 1.206(2) no
N1 C7 . . 1.4018(18) no
N1 C9 . . 1.4939(19) no
N2 C7 . . 1.378(2) no
N2 C8 . . 1.3666(19) no
N2 H2N . . 0.84(2) no
N3 C23 . . 1.4052(18) no
N3 C25 . . 1.4996(19) no
N4 C23 . . 1.375(2) no
N4 C24 . . 1.3681(19) no
N4 H4N . . 0.875(19) no
C1 C6 . . 1.394(2) no
C1 C2 . . 1.383(2) no
C2 C3 . . 1.387(2) no
C3 C4 . . 1.385(3) no
C4 C5 . . 1.376(3) no
C5 C6 . . 1.388(2) no
C8 C9 . . 1.538(2) no
C9 C10 . . 1.5250(19) no
C9 C11 . . 1.5254(19) no
C11 C16 . . 1.397(2) no
C11 C12 . . 1.391(2) no
C12 C13 . . 1.393(2) no
C13 C14 . . 1.375(2) no
C14 C15 . . 1.381(2) no
C15 C16 . . 1.387(2) no
C2 H2 . . 0.9500 no
C3 H3 . . 0.9500 no
C5 H5 . . 0.9500 no
C6 H6 . . 0.9500 no
C10 H10A . . 0.9800 no
C10 H10B . . 0.9800 no
C10 H10C . . 0.9800 no
C12 H12 . . 0.9500 no
C13 H13 . . 0.9500 no
C15 H15 . . 0.9500 no
C16 H16 . . 0.9500 no
C17 C22 . . 1.393(2) no
C17 C18 . . 1.383(2) no
C18 C19 . . 1.386(2) no
C19 C20 . . 1.384(3) no
C20 C21 . . 1.376(2) no
C21 C22 . . 1.390(2) no
C24 C25 . . 1.537(2) no
C25 C26 . . 1.5281(19) no
C25 C27 . . 1.5249(19) no
C27 C32 . . 1.398(2) no
C27 C28 . . 1.390(2) no
C28 C29 . . 1.386(2) no
C29 C30 . . 1.376(2) no
C30 C31 . . 1.375(2) no
C31 C32 . . 1.390(2) no
C18 H18 . . 0.9500 no
C19 H19 . . 0.9500 no
C21 H21 . . 0.9500 no
C22 H22 . . 0.9500 no
C26 H26A . . 0.9800 no
C26 H26B . . 0.9800 no
C26 H26C . . 0.9800 no
C28 H28 . . 0.9500 no
C29 H29 . . 0.9500 no
C31 H31 . . 0.9500 no
C32 H32 . . 0.9500 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 H2N O5 2_655 0.84(2) 2.23(2) 2.9383(17) 143.0(18) yes
N4 H4N O1 2_655 0.875(19) 2.103(19) 2.8595(17) 144.4(17) yes
C6 H6 O6 1_645 0.95 2.53 3.339(2) 143 y
C16 H16 O7 1_545 0.95 2.38 3.2330(18) 149 y
C26 H26C O4 1_465 0.98 2.41 3.358(2) 162 y
C32 H32 O3 1_455 0.95 2.38 3.2715(19) 155 y
C3 H3 F1 2_756 0.95 2.76 3.308(2) 118 y
C29 H29 F1 2_666 0.95 2.66 3.3715(19) 133 y
C13 H13 F2 2_666 0.95 2.75 3.4627(19) 133 y
C19 H19 F2 2_666 0.95 2.69 3.223(2) 116 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
O3 S1 N1 C7 . . . . 169.06(11) no
O3 S1 N1 C9 . . . . -23.58(13) no
O4 S1 N1 C7 . . . . 39.41(13) no
O4 S1 N1 C9 . . . . -153.24(11) no
C1 S1 N1 C7 . . . . -76.64(12) no
C1 S1 N1 C9 . . . . 90.72(12) no
O3 S1 C1 C2 . . . . 2.56(16) no
O3 S1 C1 C6 . . . . 179.52(13) no
O4 S1 C1 C2 . . . . 135.82(14) no
O4 S1 C1 C6 . . . . -47.21(15) no
N1 S1 C1 C2 . . . . -109.44(14) no
N1 S1 C1 C6 . . . . 67.53(14) no
O7 S2 N3 C23 . . . . 168.37(12) no
O7 S2 N3 C25 . . . . -24.06(13) no
O8 S2 N3 C23 . . . . 38.58(13) no
O8 S2 N3 C25 . . . . -153.85(11) no
C17 S2 N3 C23 . . . . -77.60(13) no
C17 S2 N3 C25 . . . . 89.98(12) no
O7 S2 C17 C18 . . . . -0.26(17) no
O7 S2 C17 C22 . . . . 177.31(13) no
O8 S2 C17 C18 . . . . 132.76(15) no
O8 S2 C17 C22 . . . . -49.67(16) no
N3 S2 C17 C18 . . . . -112.11(15) no
N3 S2 C17 C22 . . . . 65.46(15) no
S1 N1 C9 C8 . . . . -170.14(9) no
S1 N1 C9 C10 . . . . 76.29(14) no
S1 N1 C9 C11 . . . . -54.40(15) no
S1 N1 C7 O1 . . . . -8.4(2) no
S1 N1 C7 N2 . . . . 170.79(9) no
C9 N1 C7 O1 . . . . -177.21(14) no
C9 N1 C7 N2 . . . . 2.00(15) no
C7 N1 C9 C8 . . . . -1.56(14) no
C7 N1 C9 C10 . . . . -115.13(13) no
C7 N1 C9 C11 . . . . 114.18(13) no
C7 N2 C8 O2 . . . . -179.43(14) no
C7 N2 C8 C9 . . . . 0.64(16) no
C8 N2 C7 O1 . . . . 177.57(14) no
C8 N2 C7 N1 . . . . -1.63(16) no
C25 N3 C23 O5 . . . . -178.52(14) no
S2 N3 C23 O5 . . . . -9.5(2) no
S2 N3 C23 N4 . . . . 169.79(10) no
C23 N3 C25 C27 . . . . 117.74(12) no
C25 N3 C23 N4 . . . . 0.80(15) no
S2 N3 C25 C24 . . . . -168.02(9) no
S2 N3 C25 C26 . . . . 78.89(14) no
S2 N3 C25 C27 . . . . -51.16(15) no
C23 N3 C25 C24 . . . . 0.88(14) no
C23 N3 C25 C26 . . . . -112.22(13) no
C23 N4 C24 O6 . . . . -177.93(14) no
C24 N4 C23 O5 . . . . 176.83(14) no
C24 N4 C23 N3 . . . . -2.48(16) no
C23 N4 C24 C25 . . . . 3.07(16) no
S1 C1 C2 C3 . . . . 174.66(14) no
C2 C1 C6 C5 . . . . 3.8(3) no
C6 C1 C2 C3 . . . . -2.2(3) no
S1 C1 C6 C5 . . . . -173.13(13) no
C1 C2 C3 C4 . . . . -1.5(3) no
C2 C3 C4 Cl1 . . . . -175.76(15) no
C2 C3 C4 C5 . . . . 3.6(3) no
Cl1 C4 C5 C6 . . . . 177.33(14) no
C3 C4 C5 C6 . . . . -2.1(3) no
C4 C5 C6 C1 . . . . -1.6(3) no
O2 C8 C9 C11 . . . . 63.69(17) no
O2 C8 C9 C10 . . . . -63.03(18) no
N2 C8 C9 C11 . . . . -116.37(12) no
N2 C8 C9 N1 . . . . 0.56(13) no
N2 C8 C9 C10 . . . . 116.91(12) no
O2 C8 C9 N1 . . . . -179.38(13) no
C8 C9 C11 C12 . . . . -133.46(14) no
C8 C9 C11 C16 . . . . 48.46(17) no
C10 C9 C11 C12 . . . . -11.6(2) no
C10 C9 C11 C16 . . . . 170.35(14) no
N1 C9 C11 C12 . . . . 116.69(15) no
N1 C9 C11 C16 . . . . -61.39(17) no
C9 C11 C12 C13 . . . . -176.64(15) no
C12 C11 C16 C15 . . . . -0.9(2) no
C16 C11 C12 C13 . . . . 1.4(2) no
C9 C11 C16 C15 . . . . 177.24(14) no
C11 C12 C13 C14 . . . . -0.5(2) no
C12 C13 C14 C15 . . . . -1.1(3) no
C12 C13 C14 F1 . . . . 178.57(15) no
C13 C14 C15 C16 . . . . 1.6(3) no
F1 C14 C15 C16 . . . . -178.08(15) no
C14 C15 C16 C11 . . . . -0.6(2) no
S2 C17 C18 C19 . . . . 175.79(15) no
C22 C17 C18 C19 . . . . -1.7(3) no
S2 C17 C22 C21 . . . . -174.77(13) no
C18 C17 C22 C21 . . . . 2.8(3) no
C17 C18 C19 C20 . . . . -0.7(3) no
C18 C19 C20 Cl2 . . . . -177.81(15) no
C18 C19 C20 C21 . . . . 2.0(3) no
Cl2 C20 C21 C22 . . . . 178.86(14) no
C19 C20 C21 C22 . . . . -1.0(3) no
C20 C21 C22 C17 . . . . -1.4(3) no
O6 C24 C25 N3 . . . . 178.72(13) no
O6 C24 C25 C26 . . . . -65.50(18) no
O6 C24 C25 C27 . . . . 60.94(18) no
N4 C24 C25 N3 . . . . -2.26(13) no
N4 C24 C25 C26 . . . . 113.52(13) no
N4 C24 C25 C27 . . . . -120.04(12) no
N3 C25 C27 C28 . . . . 111.40(15) no
N3 C25 C27 C32 . . . . -66.12(17) no
C24 C25 C27 C28 . . . . -137.80(14) no
C24 C25 C27 C32 . . . . 44.67(18) no
C26 C25 C27 C28 . . . . -16.1(2) no
C26 C25 C27 C32 . . . . 166.34(14) no
C25 C27 C28 C29 . . . . -176.22(15) no
C32 C27 C28 C29 . . . . 1.3(2) no
C25 C27 C32 C31 . . . . 176.65(15) no
C28 C27 C32 C31 . . . . -1.0(2) no
C27 C28 C29 C30 . . . . -0.1(3) no
C28 C29 C30 F2 . . . . 178.10(16) no
C28 C29 C30 C31 . . . . -1.4(3) no
F2 C30 C31 C32 . . . . -177.78(15) no
C29 C30 C31 C32 . . . . 1.8(3) no
C30 C31 C32 C27 . . . . -0.5(2) no
