#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/92/2229268.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_2229268
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Chantrapromma, Suchada'
'Sumangala, V.'
'Nagaraja, G. K.'
'Poojary, Boja'
_publ_section_title
;
 1-{4-Chloro-2-[2-(2-fluorophenyl)-1,3-dithiolan-2-yl]phenyl}-2-methyl-1H-imidazole-5-carbaldehyde
;
_journal_coeditor_code           WN2418
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o496
_journal_page_last               o497
_journal_paper_doi               10.1107/S1600536811002595
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C20 H16 Cl F N2 O S2'
_chemical_formula_moiety         'C20 H16 Cl F N2 O S2'
_chemical_formula_sum            'C20 H16 Cl F N2 O S2'
_chemical_formula_weight         418.92
_chemical_melting_point_gt       431
_chemical_melting_point_lt       433
_chemical_name_systematic
1-{4-Chloro-2-[2-(2-fluorophenyl)-1,3-dithiolan-2-yl]phenyl}-2-methyl-1H-imidazole-5-carbaldehyde
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 116.8070(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.5654(3)
_cell_length_b                   9.27300(10)
_cell_length_c                   24.7174(4)
_cell_measurement_reflns_used    11058
_cell_measurement_temperature    297
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      2.31
_cell_volume                     3797.96(10)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      297
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            42050
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.31
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.443
_exptl_absorpt_correction_T_max  0.8329
_exptl_absorpt_correction_T_min  0.7871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.43
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.288
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     498
_refine_ls_number_reflns         11058
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0494P)²+1.2334P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1100
_reflns_number_gt                8238
_reflns_number_total             11058
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn2418.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229268
_cod_database_fobs_code          2229268
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1A 0.25942(3) 0.62718(5) 0.73463(3) 0.06226(14) Uani d . 1 . .
S S1A 0.30891(3) 0.06420(5) 0.76209(2) 0.04776(11) Uani d . 1 . .
S S2A 0.35008(3) 0.12181(5) 0.89061(2) 0.04827(11) Uani d . 1 . .
F F1A 0.45561(7) 0.10894(12) 0.75343(5) 0.0543(3) Uani d . 1 . .
O O1A 0.45746(10) 0.3552(2) 0.97799(8) 0.0808(5) Uani d . 1 . .
N N1A 0.54863(7) 0.30739(13) 0.90641(6) 0.0333(3) Uani d . 1 . .
N N2A 0.67475(8) 0.22391(16) 0.94763(7) 0.0462(3) Uani d . 1 . .
C C1A 0.49232(10) 0.03084(17) 0.80578(8) 0.0411(3) Uani d . 1 . .
C C2A 0.55553(11) -0.0572(2) 0.81286(10) 0.0536(5) Uani d . 1 . .
H H2AA 0.5715 -0.0656 0.7823 0.064 Uiso calc R 1 . .
C C3A 0.59483(12) -0.1329(2) 0.86655(11) 0.0603(5) Uani d . 1 . .
H H3AA 0.6381 -0.1927 0.8727 0.072 Uiso calc R 1 . .
C C4A 0.56967(12) -0.1193(2) 0.91058(10) 0.0562(5) Uani d . 1 . .
H H4AA 0.5967 -0.1692 0.9469 0.067 Uiso calc R 1 . .
C C5A 0.50453(10) -0.03238(17) 0.90177(8) 0.0439(4) Uani d . 1 . .
H H5AA 0.4878 -0.0263 0.9319 0.053 Uiso calc R 1 . .
C C6A 0.46387(9) 0.04589(15) 0.84846(7) 0.0352(3) Uani d . 1 . .
C C7A 0.38948(9) 0.13927(16) 0.83468(7) 0.0342(3) Uani d . 1 . .
C C8A 0.23702(12) 0.0129(3) 0.78845(10) 0.0632(5) Uani d . 1 . .
H H8AA 0.2005 0.0923 0.7835 0.076 Uiso calc R 1 . .
H H8AB 0.2055 -0.0688 0.7654 0.076 Uiso calc R 1 . .
C C9A 0.28267(13) -0.0262(2) 0.85399(11) 0.0617(5) Uani d . 1 . .
H H9AA 0.3130 -0.1145 0.8587 0.074 Uiso calc R 1 . .
H H9AB 0.2459 -0.0405 0.8716 0.074 Uiso calc R 1 . .
C C10A 0.40297(9) 0.30204(16) 0.82977(7) 0.0328(3) Uani d . 1 . .
C C11A 0.33688(9) 0.38578(18) 0.79124(8) 0.0391(3) Uani d . 1 . .
H H11A 0.2872 0.3414 0.7689 0.047 Uiso calc R 1 . .
C C12A 0.34365(9) 0.53227(18) 0.78570(8) 0.0403(3) Uani d . 1 . .
C C13A 0.41532(10) 0.60404(18) 0.81777(8) 0.0449(4) Uani d . 1 . .
H H13A 0.4193 0.7029 0.8135 0.054 Uiso calc R 1 . .
C C14A 0.48118(10) 0.52407(17) 0.85662(8) 0.0418(4) Uani d . 1 . .
H H14A 0.5303 0.5702 0.8788 0.050 Uiso calc R 1 . .
C C15A 0.47569(9) 0.37588(16) 0.86333(7) 0.0330(3) Uani d . 1 . .
C C16A 0.61461(9) 0.27685(17) 0.89769(7) 0.0368(3) Uani d . 1 . .
C C17A 0.64670(11) 0.22370(19) 0.98946(8) 0.0463(4) Uani d . 1 . .
H H17A 0.6764 0.1917 1.0291 0.056 Uiso calc R 1 . .
C C18A 0.56970(10) 0.27589(17) 0.96678(7) 0.0392(3) Uani d . 1 . .
C C19A 0.52354(13) 0.3053(2) 0.99857(9) 0.0527(4) Uani d . 1 . .
H H19A 0.5476 0.2831 1.0397 0.063 Uiso calc R 1 . .
C C20A 0.61982(11) 0.3074(2) 0.84079(8) 0.0501(4) Uani d . 1 . .
H H20A 0.6601 0.2465 0.8384 0.075 Uiso calc R 1 . .
H H20B 0.6342 0.4066 0.8403 0.075 Uiso calc R 1 . .
H H20C 0.5685 0.2887 0.8068 0.075 Uiso calc R 1 . .
Cl Cl1B -0.11743(3) 0.82366(6) 0.82366(2) 0.06218(14) Uani d . 1 A .
S S1B -0.06051(3) 0.25797(5) 0.84138(2) 0.04791(11) Uani d . 1 . .
S S2B 0.07738(3) 0.33592(5) 0.81837(2) 0.04785(11) Uani d . 1 . .
F F1B 0.00272(8) 0.29431(15) 0.97221(5) 0.0681(3) Uani d . 1 . .
O O1B 0.20278(10) 0.6108(2) 0.86047(7) 0.0772(5) Uani d . 1 . .
N N1B 0.18622(7) 0.50963(14) 0.96952(6) 0.0348(3) Uani d . 1 . .
N N2B 0.28898(9) 0.41459(16) 1.04951(7) 0.0475(3) Uani d . 1 . .
C C1B 0.06791(12) 0.2203(2) 0.97587(8) 0.0479(4) Uani d . 1 A .
C C2B 0.10655(16) 0.1275(2) 1.02414(9) 0.0659(6) Uani d . 1 . .
H H2BA 0.0872 0.1141 1.0525 0.079 Uiso calc R 1 . .
C C3B 0.17401(15) 0.0555(2) 1.02951(10) 0.0688(6) Uani d . 1 . .
H H3BA 0.2010 -0.0071 1.0618 0.083 Uiso calc R 1 . .
C C4B 0.20137(12) 0.0759(2) 0.98734(10) 0.0593(5) Uani d . 1 . .
H H4BA 0.2476 0.0281 0.9913 0.071 Uiso calc R 1 . .
C C5B 0.16075(10) 0.16754(18) 0.93844(8) 0.0448(4) Uani d . 1 A .
H H5BA 0.1797 0.1786 0.9097 0.054 Uiso calc R 1 . .
C C6B 0.09254(9) 0.24306(16) 0.93159(7) 0.0357(3) Uani d . 1 . .
C C7B 0.04282(9) 0.33975(17) 0.87717(7) 0.0336(3) Uani d . 1 A .
C C10B 0.04177(9) 0.50073(16) 0.89252(6) 0.0321(3) Uani d . 1 . .
C C11B -0.02824(9) 0.58123(18) 0.86003(7) 0.0374(3) Uani d . 1 A .
H H11B -0.0750 0.5347 0.8329 0.045 Uiso calc R 1 . .
C C12B -0.02917(10) 0.72888(18) 0.86748(7) 0.0401(3) Uani d . 1 . .
C C13B 0.03757(11) 0.80291(19) 0.90805(8) 0.0464(4) Uani d . 1 A .
H H13B 0.0361 0.9022 0.9128 0.056 Uiso calc R 1 . .
C C14B 0.10674(10) 0.72464(18) 0.94136(8) 0.0445(4) Uani d . 1 . .
H H14B 0.1525 0.7718 0.9696 0.053 Uiso calc R 1 A .
C C15B 0.10945(9) 0.57683(17) 0.93361(7) 0.0342(3) Uani d . 1 A .
C C16B 0.21586(10) 0.47013(18) 1.02890(7) 0.0399(3) Uani d . 1 . .
C C17B 0.30732(10) 0.42030(19) 1.00227(9) 0.0468(4) Uani d . 1 . .
H H17B 0.3557 0.3880 1.0039 0.056 Uiso calc R 1 . .
C C18B 0.24570(9) 0.47949(17) 0.95176(8) 0.0396(3) Uani d . 1 . .
C C19B 0.24897(12) 0.5274(2) 0.89772(9) 0.0532(4) Uani d . 1 . .
H H19B 0.2906 0.4909 0.8906 0.064 Uiso calc R 1 . .
C C20B 0.17221(12) 0.4943(3) 1.06578(9) 0.0579(5) Uani d . 1 . .
H H20D 0.1919 0.4284 1.0993 0.087 Uiso calc R 1 . .
H H20E 0.1155 0.4786 1.0411 0.087 Uiso calc R 1 . .
H H20F 0.1809 0.5915 1.0807 0.087 Uiso calc R 1 . .
C C8BA -0.0620(2) 0.1950(5) 0.77250(17) 0.0664(10) Uani d P 0.849(10) A 1
H H8BA -0.0914 0.1048 0.7604 0.080 Uiso calc PR 0.849(10) A 1
H H8BB -0.0889 0.2650 0.7404 0.080 Uiso calc PR 0.849(10) A 1
C C9BA 0.0235(2) 0.1734(4) 0.78267(16) 0.0593(9) Uani d P 0.849(10) A 1
H H9BA 0.0250 0.1576 0.7444 0.071 Uiso calc PR 0.849(10) A 1
H H9BB 0.0474 0.0907 0.8086 0.071 Uiso calc PR 0.849(10) A 1
C C8BB -0.0388(12) 0.1405(19) 0.7960(9) 0.053(4) Uiso d P 0.151(10) A 2
H H8BC -0.0007 0.0679 0.8208 0.064 Uiso calc PR 0.151(10) A 2
H H8BD -0.0877 0.0923 0.7676 0.064 Uiso calc PR 0.151(10) A 2
C C9BB -0.0027(15) 0.228(3) 0.7614(11) 0.075(6) Uiso d P 0.151(10) A 2
H H9BC -0.0434 0.2900 0.7314 0.090 Uiso calc PR 0.151(10) A 2
H H9BD 0.0188 0.1649 0.7410 0.090 Uiso calc PR 0.151(10) A 2
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'
F F 0.0171 0.0103 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8A S1A C7A . . 98.85(9) ?
C9A S2A C7A . . 96.37(9) ?
C16A N1A C18A . . 106.68(13) ?
C16A N1A C15A . . 125.89(13) ?
C18A N1A C15A . . 126.99(13) ?
C16A N2A C17A . . 105.00(14) ?
F1A C1A C2A . . 117.88(16) ?
F1A C1A C6A . . 118.02(14) ?
C2A C1A C6A . . 124.10(17) ?
C1A C2A C3A . . 118.32(19) ?
C1A C2A H2AA . . 120.8 ?
C3A C2A H2AA . . 120.8 ?
C4A C3A C2A . . 119.60(17) ?
C4A C3A H3AA . . 120.2 ?
C2A C3A H3AA . . 120.2 ?
C3A C4A C5A . . 120.96(18) ?
C3A C4A H4AA . . 119.5 ?
C5A C4A H4AA . . 119.5 ?
C4A C5A C6A . . 120.95(18) ?
C4A C5A H5AA . . 119.5 ?
C6A C5A H5AA . . 119.5 ?
C1A C6A C5A . . 116.03(15) ?
C1A C6A C7A . . 120.22(14) ?
C5A C6A C7A . . 123.69(15) ?
C6A C7A C10A . . 114.07(12) ?
C6A C7A S2A . . 114.03(11) ?
C10A C7A S2A . . 106.19(10) ?
C6A C7A S1A . . 104.64(10) ?
C10A C7A S1A . . 112.03(10) ?
S2A C7A S1A . . 105.68(7) ?
C9A C8A S1A . . 107.87(13) ?
C9A C8A H8AA . . 110.1 ?
S1A C8A H8AA . . 110.1 ?
C9A C8A H8AB . . 110.1 ?
S1A C8A H8AB . . 110.1 ?
H8AA C8A H8AB . . 108.4 ?
C8A C9A S2A . . 106.58(14) ?
C8A C9A H9AA . . 110.4 ?
S2A C9A H9AA . . 110.4 ?
C8A C9A H9AB . . 110.4 ?
S2A C9A H9AB . . 110.4 ?
H9AA C9A H9AB . . 108.6 ?
C11A C10A C15A . . 116.47(14) ?
C11A C10A C7A . . 118.17(13) ?
C15A C10A C7A . . 125.28(13) ?
C12A C11A C10A . . 121.56(15) ?
C12A C11A H11A . . 119.2 ?
C10A C11A H11A . . 119.2 ?
C13A C12A C11A . . 121.89(15) ?
C13A C12A Cl1A . . 119.50(13) ?
C11A C12A Cl1A . . 118.58(13) ?
C12A C13A C14A . . 117.65(15) ?
C12A C13A H13A . . 121.2 ?
C14A C13A H13A . . 121.2 ?
C13A C14A C15A . . 121.52(15) ?
C13A C14A H14A . . 119.2 ?
C15A C14A H14A . . 119.2 ?
C14A C15A C10A . . 120.89(14) ?
C14A C15A N1A . . 115.37(13) ?
C10A C15A N1A . . 123.74(13) ?
N2A C16A N1A . . 111.56(14) ?
N2A C16A C20A . . 124.43(15) ?
N1A C16A C20A . . 123.92(14) ?
N2A C17A C18A . . 112.22(15) ?
N2A C17A H17A . . 123.9 ?
C18A C17A H17A . . 123.9 ?
C17A C18A N1A . . 104.49(14) ?
C17A C18A C19A . . 128.22(17) ?
N1A C18A C19A . . 127.03(16) ?
O1A C19A C18A . . 126.8(2) ?
O1A C19A H19A . . 116.6 ?
C18A C19A H19A . . 116.6 ?
C16A C20A H20A . . 109.5 ?
C16A C20A H20B . . 109.5 ?
H20A C20A H20B . . 109.5 ?
C16A C20A H20C . . 109.5 ?
H20A C20A H20C . . 109.5 ?
H20B C20A H20C . . 109.5 ?
C8BB S1B C7B . . 94.2(6) ?
C8BA S1B C7B . . 98.91(10) ?
C9BA S2B C7B . . 95.08(10) ?
C9BB S2B C7B . . 99.7(6) ?
C16B N1B C18B . . 107.07(13) ?
C16B N1B C15B . . 125.95(13) ?
C18B N1B C15B . . 126.91(13) ?
C16B N2B C17B . . 105.43(14) ?
F1B C1B C6B . . 118.32(15) ?
F1B C1B C2B . . 118.18(18) ?
C6B C1B C2B . . 123.49(18) ?
C3B C2B C1B . . 118.9(2) ?
C3B C2B H2BA . . 120.6 ?
C1B C2B H2BA . . 120.6 ?
C4B C3B C2B . . 119.8(2) ?
C4B C3B H3BA . . 120.1 ?
C2B C3B H3BA . . 120.1 ?
C3B C4B C5B . . 120.48(19) ?
C3B C4B H4BA . . 119.8 ?
C5B C4B H4BA . . 119.8 ?
C6B C5B C4B . . 121.45(19) ?
C6B C5B H5BA . . 119.3 ?
C4B C5B H5BA . . 119.3 ?
C1B C6B C5B . . 115.88(16) ?
C1B C6B C7B . . 120.13(14) ?
C5B C6B C7B . . 123.89(15) ?
C6B C7B C10B . . 114.84(12) ?
C6B C7B S2B . . 113.37(10) ?
C10B C7B S2B . . 105.14(10) ?
C6B C7B S1B . . 105.13(10) ?
C10B C7B S1B . . 112.60(10) ?
S2B C7B S1B . . 105.52(7) ?
C11B C10B C15B . . 116.49(14) ?
C11B C10B C7B . . 119.18(13) ?
C15B C10B C7B . . 124.05(13) ?
C12B C11B C10B . . 121.13(15) ?
C12B C11B H11B . . 119.4 ?
C10B C11B H11B . . 119.4 ?
C13B C12B C11B . . 122.02(15) ?
C13B C12B Cl1B . . 119.17(13) ?
C11B C12B Cl1B . . 118.81(13) ?
C12B C13B C14B . . 117.58(16) ?
C12B C13B H13B . . 121.2 ?
C14B C13B H13B . . 121.2 ?
C13B C14B C15B . . 121.29(15) ?
C13B C14B H14B . . 119.4 ?
C15B C14B H14B . . 119.4 ?
C14B C15B C10B . . 121.45(14) ?
C14B C15B N1B . . 115.49(14) ?
C10B C15B N1B . . 123.05(14) ?
N2B C16B N1B . . 111.43(15) ?
N2B C16B C20B . . 124.95(16) ?
N1B C16B C20B . . 123.55(15) ?
N2B C17B C18B . . 111.66(15) ?
N2B C17B H17B . . 124.2 ?
C18B C17B H17B . . 124.2 ?
C17B C18B N1B . . 104.40(15) ?
C17B C18B C19B . . 127.11(16) ?
N1B C18B C19B . . 127.28(16) ?
O1B C19B C18B . . 126.31(19) ?
O1B C19B H19B . . 116.8 ?
C18B C19B H19B . . 116.8 ?
C16B C20B H20D . . 109.5 ?
C16B C20B H20E . . 109.5 ?
H20D C20B H20E . . 109.5 ?
C16B C20B H20F . . 109.5 ?
H20D C20B H20F . . 109.5 ?
H20E C20B H20F . . 109.5 ?
C9BA C8BA S1B . . 108.8(2) ?
C9BA C8BA H8BA . . 109.9 ?
S1B C8BA H8BA . . 109.9 ?
C9BA C8BA H8BB . . 109.9 ?
S1B C8BA H8BB . . 109.9 ?
H8BA C8BA H8BB . . 108.3 ?
C8BA C9BA S2B . . 106.3(2) ?
C8BA C9BA H9BA . . 110.5 ?
S2B C9BA H9BA . . 110.5 ?
C8BA C9BA H9BB . . 110.5 ?
S2B C9BA H9BB . . 110.5 ?
H9BA C9BA H9BB . . 108.7 ?
C9BB C8BB S1B . . 108.3(14) ?
C9BB C8BB H8BC . . 110.0 ?
S1B C8BB H8BC . . 110.0 ?
C9BB C8BB H8BD . . 110.0 ?
S1B C8BB H8BD . . 110.0 ?
H8BC C8BB H8BD . . 108.4 ?
C8BB C9BB S2B . . 105.7(16) ?
C8BB C9BB H9BC . . 110.6 ?
S2B C9BB H9BC . . 110.6 ?
C8BB C9BB H9BD . . 110.6 ?
S2B C9BB H9BD . . 110.6 ?
H9BC C9BB H9BD . . 108.7 ?
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
Cl1A C12A . 1.7415(16) ?
S1A C8A . 1.794(2) ?
S1A C7A . 1.8764(16) ?
S2A C9A . 1.802(2) ?
S2A C7A . 1.8396(16) ?
F1A C1A . 1.367(2) ?
O1A C19A . 1.190(2) ?
N1A C16A . 1.3659(19) ?
N1A C18A . 1.392(2) ?
N1A C15A . 1.4389(19) ?
N2A C16A . 1.330(2) ?
N2A C17A . 1.351(2) ?
C1A C2A . 1.374(2) ?
C1A C6A . 1.383(2) ?
C2A C3A . 1.383(3) ?
C2A H2AA . 0.9300 ?
C3A C4A . 1.370(3) ?
C3A H3AA . 0.9300 ?
C4A C5A . 1.387(3) ?
C4A H4AA . 0.9300 ?
C5A C6A . 1.391(2) ?
C5A H5AA . 0.9300 ?
C6A C7A . 1.533(2) ?
C7A C10A . 1.544(2) ?
C8A C9A . 1.495(3) ?
C8A H8AA . 0.9700 ?
C8A H8AB . 0.9700 ?
C9A H9AA . 0.9700 ?
C9A H9AB . 0.9700 ?
C10A C11A . 1.400(2) ?
C10A C15A . 1.403(2) ?
C11A C12A . 1.377(2) ?
C11A H11A . 0.9300 ?
C12A C13A . 1.375(2) ?
C13A C14A . 1.381(2) ?
C13A H13A . 0.9300 ?
C14A C15A . 1.393(2) ?
C14A H14A . 0.9300 ?
C16A C20A . 1.480(2) ?
C17A C18A . 1.367(2) ?
C17A H17A . 0.9300 ?
C18A C19A . 1.426(2) ?
C19A H19A . 0.9300 ?
C20A H20A . 0.9600 ?
C20A H20B . 0.9600 ?
C20A H20C . 0.9600 ?
Cl1B C12B . 1.7407(16) ?
S1B C8BB . 1.737(15) ?
S1B C8BA . 1.788(3) ?
S1B C7B . 1.8728(15) ?
S2B C9BA . 1.804(3) ?
S2B C9BB . 1.82(2) ?
S2B C7B . 1.8349(15) ?
F1B C1B . 1.358(2) ?
O1B C19B . 1.212(3) ?
N1B C16B . 1.365(2) ?
N1B C18B . 1.388(2) ?
N1B C15B . 1.4375(19) ?
N2B C16B . 1.321(2) ?
N2B C17B . 1.357(2) ?
C1B C6B . 1.379(2) ?
C1B C2B . 1.381(3) ?
C2B C3B . 1.372(3) ?
C2B H2BA . 0.9300 ?
C3B C4B . 1.363(3) ?
C3B H3BA . 0.9300 ?
C4B C5B . 1.389(3) ?
C4B H4BA . 0.9300 ?
C5B C6B . 1.389(2) ?
C5B H5BA . 0.9300 ?
C6B C7B . 1.531(2) ?
C7B C10B . 1.542(2) ?
C10B C11B . 1.397(2) ?
C10B C15B . 1.399(2) ?
C11B C12B . 1.383(2) ?
C11B H11B . 0.9300 ?
C12B C13B . 1.375(2) ?
C13B C14B . 1.378(2) ?
C13B H13B . 0.9300 ?
C14B C15B . 1.388(2) ?
C14B H14B . 0.9300 ?
C16B C20B . 1.485(2) ?
C17B C18B . 1.371(2) ?
C17B H17B . 0.9300 ?
C18B C19B . 1.435(3) ?
C19B H19B . 0.9300 ?
C20B H20D . 0.9600 ?
C20B H20E . 0.9600 ?
C20B H20F . 0.9600 ?
C8BA C9BA . 1.504(5) ?
C8BA H8BA . 0.9700 ?
C8BA H8BB . 0.9700 ?
C9BA H9BA . 0.9700 ?
C9BA H9BB . 0.9700 ?
C8BB C9BB . 1.54(3) ?
C8BB H8BC . 0.9700 ?
C8BB H8BD . 0.9700 ?
C9BB H9BC . 0.9700 ?
C9BB H9BD . 0.9700 ?
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
C17B H17B O1A 1_555 0.93 2.27 3.163(3) 160 y
C20A H20C F1A 1_555 0.96 2.53 3.377(2) 147 y
C2A H2AA Cg5 2_646 0.93 2.81 3.727(2) 167 y
C13A H13A Cg4 1_565 0.93 2.98 3.7764(19) 144 y
C13B H13B Cg2 1_565 0.93 2.93 3.716(2) 143 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
F1A C1A C2A C3A . . . . 177.86(16) ?
C6A C1A C2A C3A . . . . -1.8(3) ?
C1A C2A C3A C4A . . . . 0.5(3) ?
C2A C3A C4A C5A . . . . 1.0(3) ?
C3A C4A C5A C6A . . . . -1.3(3) ?
F1A C1A C6A C5A . . . . -178.19(14) ?
C2A C1A C6A C5A . . . . 1.4(2) ?
F1A C1A C6A C7A . . . . 4.3(2) ?
C2A C1A C6A C7A . . . . -176.03(16) ?
C4A C5A C6A C1A . . . . 0.1(2) ?
C4A C5A C6A C7A . . . . 177.49(15) ?
C1A C6A C7A C10A . . . . -67.81(18) ?
C5A C6A C7A C10A . . . . 114.93(16) ?
C1A C6A C7A S2A . . . . 169.95(12) ?
C5A C6A C7A S2A . . . . -7.31(19) ?
C1A C6A C7A S1A . . . . 54.97(16) ?
C5A C6A C7A S1A . . . . -122.29(14) ?
C9A S2A C7A C6A . . . . -89.25(13) ?
C9A S2A C7A C10A . . . . 144.28(12) ?
C9A S2A C7A S1A . . . . 25.12(10) ?
C8A S1A C7A C6A . . . . 119.73(12) ?
C8A S1A C7A C10A . . . . -116.18(12) ?
C8A S1A C7A S2A . . . . -0.96(11) ?
C7A S1A C8A C9A . . . . -30.39(17) ?
S1A C8A C9A S2A . . . . 51.40(18) ?
C7A S2A C9A C8A . . . . -47.47(16) ?
C6A C7A C10A C11A . . . . 150.01(14) ?
S2A C7A C10A C11A . . . . -83.54(15) ?
S1A C7A C10A C11A . . . . 31.36(17) ?
C6A C7A C10A C15A . . . . -33.5(2) ?
S2A C7A C10A C15A . . . . 92.96(15) ?
S1A C7A C10A C15A . . . . -152.14(13) ?
C15A C10A C11A C12A . . . . 1.4(2) ?
C7A C10A C11A C12A . . . . 178.23(15) ?
C10A C11A C12A C13A . . . . -0.3(3) ?
C10A C11A C12A Cl1A . . . . 177.61(13) ?
C11A C12A C13A C14A . . . . -0.5(3) ?
Cl1A C12A C13A C14A . . . . -178.33(14) ?
C12A C13A C14A C15A . . . . 0.0(3) ?
C13A C14A C15A C10A . . . . 1.2(3) ?
C13A C14A C15A N1A . . . . -178.58(15) ?
C11A C10A C15A C14A . . . . -1.9(2) ?
C7A C10A C15A C14A . . . . -178.42(15) ?
C11A C10A C15A N1A . . . . 177.91(14) ?
C7A C10A C15A N1A . . . . 1.4(2) ?
C16A N1A C15A C14A . . . . -75.4(2) ?
C18A N1A C15A C14A . . . . 96.07(19) ?
C16A N1A C15A C10A . . . . 104.81(18) ?
C18A N1A C15A C10A . . . . -83.7(2) ?
C17A N2A C16A N1A . . . . -1.26(19) ?
C17A N2A C16A C20A . . . . 175.30(17) ?
C18A N1A C16A N2A . . . . 2.08(18) ?
C15A N1A C16A N2A . . . . 174.99(14) ?
C18A N1A C16A C20A . . . . -174.49(16) ?
C15A N1A C16A C20A . . . . -1.6(2) ?
C16A N2A C17A C18A . . . . -0.1(2) ?
N2A C17A C18A N1A . . . . 1.30(19) ?
N2A C17A C18A C19A . . . . -173.19(17) ?
C16A N1A C18A C17A . . . . -1.97(17) ?
C15A N1A C18A C17A . . . . -174.77(14) ?
C16A N1A C18A C19A . . . . 172.60(17) ?
C15A N1A C18A C19A . . . . -0.2(3) ?
C17A C18A C19A O1A . . . . 177.3(2) ?
N1A C18A C19A O1A . . . . 4.0(3) ?
F1B C1B C2B C3B . . . . -177.98(19) ?
C6B C1B C2B C3B . . . . 1.3(3) ?
C1B C2B C3B C4B . . . . -0.3(3) ?
C2B C3B C4B C5B . . . . -1.0(3) ?
C3B C4B C5B C6B . . . . 1.4(3) ?
F1B C1B C6B C5B . . . . 178.35(16) ?
C2B C1B C6B C5B . . . . -0.9(3) ?
F1B C1B C6B C7B . . . . -5.0(2) ?
C2B C1B C6B C7B . . . . 175.70(18) ?
C4B C5B C6B C1B . . . . -0.4(2) ?
C4B C5B C6B C7B . . . . -176.88(16) ?
C1B C6B C7B C10B . . . . 67.24(19) ?
C5B C6B C7B C10B . . . . -116.45(16) ?
C1B C6B C7B S2B . . . . -171.85(13) ?
C5B C6B C7B S2B . . . . 4.5(2) ?
C1B C6B C7B S1B . . . . -57.09(17) ?
C5B C6B C7B S1B . . . . 119.22(15) ?
C9BA S2B C7B C6B . . . . 82.91(18) ?
C9BB S2B C7B C6B . . . . 106.1(10) ?
C9BA S2B C7B C10B . . . . -150.86(17) ?
C9BB S2B C7B C10B . . . . -127.7(10) ?
C9BA S2B C7B S1B . . . . -31.63(16) ?
C9BB S2B C7B S1B . . . . -8.4(10) ?
C8BB S1B C7B C6B . . . . -87.5(7) ?
C8BA S1B C7B C6B . . . . -111.47(19) ?
C8BB S1B C7B C10B . . . . 146.8(7) ?
C8BA S1B C7B C10B . . . . 122.8(2) ?
C8BB S1B C7B S2B . . . . 32.6(7) ?
C8BA S1B C7B S2B . . . . 8.64(19) ?
C6B C7B C10B C11B . . . . -145.03(14) ?
S2B C7B C10B C11B . . . . 89.65(14) ?
S1B C7B C10B C11B . . . . -24.74(17) ?
C6B C7B C10B C15B . . . . 41.2(2) ?
S2B C7B C10B C15B . . . . -84.13(15) ?
S1B C7B C10B C15B . . . . 161.48(12) ?
C15B C10B C11B C12B . . . . 1.5(2) ?
C7B C10B C11B C12B . . . . -172.71(14) ?
C10B C11B C12B C13B . . . . -1.7(3) ?
C10B C11B C12B Cl1B . . . . 177.78(12) ?
C11B C12B C13B C14B . . . . 0.4(3) ?
Cl1B C12B C13B C14B . . . . -179.10(14) ?
C12B C13B C14B C15B . . . . 1.0(3) ?
C13B C14B C15B C10B . . . . -1.2(3) ?
C13B C14B C15B N1B . . . . 177.64(16) ?
C11B C10B C15B C14B . . . . -0.1(2) ?
C7B C10B C15B C14B . . . . 173.82(15) ?
C11B C10B C15B N1B . . . . -178.85(13) ?
C7B C10B C15B N1B . . . . -4.9(2) ?
C16B N1B C15B C14B . . . . 81.0(2) ?
C18B N1B C15B C14B . . . . -95.36(19) ?
C16B N1B C15B C10B . . . . -100.17(19) ?
C18B N1B C15B C10B . . . . 83.4(2) ?
C17B N2B C16B N1B . . . . 0.81(19) ?
C17B N2B C16B C20B . . . . -176.26(18) ?
C18B N1B C16B N2B . . . . -1.30(19) ?
C15B N1B C16B N2B . . . . -178.28(14) ?
C18B N1B C16B C20B . . . . 175.82(17) ?
C15B N1B C16B C20B . . . . -1.2(3) ?
C16B N2B C17B C18B . . . . 0.0(2) ?
N2B C17B C18B N1B . . . . -0.8(2) ?
N2B C17B C18B C19B . . . . 167.32(17) ?
C16B N1B C18B C17B . . . . 1.20(17) ?
C15B N1B C18B C17B . . . . 178.14(15) ?
C16B N1B C18B C19B . . . . -166.85(17) ?
C15B N1B C18B C19B . . . . 10.1(3) ?
C17B C18B C19B O1B . . . . -159.9(2) ?
N1B C18B C19B O1B . . . . 5.5(3) ?
C8BB S1B C8BA C9BA . . . . -56.2(13) ?
C7B S1B C8BA C9BA . . . . 24.1(4) ?
S1B C8BA C9BA S2B . . . . -49.0(4) ?
C9BB S2B C9BA C8BA . . . . -52.7(17) ?
C7B S2B C9BA C8BA . . . . 50.0(3) ?
C8BA S1B C8BB C9BB . . . . 50.7(17) ?
C7B S1B C8BB C9BB . . . . -51.8(19) ?
S1B C8BB C9BB S2B . . . . 50(2) ?
C9BA S2B C9BB C8BB . . . . 57.1(19) ?
C7B S2B C9BB C8BB . . . . -23.2(19) ?
