##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2013-05-13
_journal_date_accepted     2013-05-27
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2013
_journal_volume     69
_journal_issue      7
_journal_page_first     o1007
_journal_page_last     o1008
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536813014621
_journal_coeditor_code     XU5707
loop_
    _publ_contact_author_name
    _publ_contact_author_address
    _publ_contact_author_email
    'Susanta K. Nayak'
;
Equipe Chimie du Solide et Matériaux, UMR 6226 Institut des Sciences
Université de Rennes 1, Campus de Beaulieu, Avenue du Général Leclerc,
35042 Rennes Cedex, France
;
 nksusa@gmail.com
    'K. N. Venugopala'
;
School of Pharmacy and Pharmacology
University of KwaZulu-Natal
Durban 4000, South Africa
;
 venugopala@ukzn.ac.za
_publ_section_title
;
{2-[(1,3-Benzothiazol-2-yl)methoxy]-5-fluorophenyl}(4-chlorophenyl)methanone
;
loop_
    _publ_author_name
    _publ_author_address
    'Venugopala, K. N.'
;
School of Pharmacy and Pharmacology
University of KwaZulu-Natal
Durban 4000, South Africa
;
    'Nayak, Susanta K.'
;
Equipe Chimie du Solide et Matériaux, UMR 6226 Institut des Sciences
Université de Rennes 1, Campus de Beaulieu, Avenue du Général Leclerc,
35042 Rennes Cedex, France
;
    'Govender, Thavendran'
;
School of Pharmacy and Pharmacology
University of KwaZulu-Natal
Durban 4000, South Africa
;
    'Kruger, Hendrik G.'
;
School of Chemistry and Physics
University of KwaZulu-Natal
Durban 4000
South Africa
;
    'Maguire, Glenn E. M.'
;
School of Chemistry and Physics
University of KwaZulu-Natal
Durban 4000
South Africa
;
data_I
_chemical_name_systematic
;
{2-[(1,3-Benzothiazol-2-yl)methoxy]-5-fluorophenyl}(4-chlorophenyl)methanone
;
_chemical_name_common     ?
_chemical_formula_moiety     'C21 H13 Cl F N O2 S'
_chemical_formula_sum     'C21 H13 Cl F N O2 S'
_chemical_formula_structural     ?
_chemical_formula_iupac     'C21 H13 Cl F N O2 S'
_chemical_formula_weight     397.84
_chemical_melting_point     419(2)
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P n a 21'
_symmetry_space_group_name_Hall     'P 2c -2n'
loop_
    _symmetry_equiv_pos_site_id
    _symmetry_equiv_pos_as_xyz
    1 x,y,z
    2 -x,-y,1/2+z
    3 1/2-x,1/2+y,1/2+z
    4 1/2+x,1/2-y,z
_cell_length_a     19.7280(6)
_cell_length_b     7.4755(3)
_cell_length_c     24.4847(7)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     3611.0(2)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     340
_cell_measurement_theta_min     2.7
_cell_measurement_theta_max     27.0
_cell_measurement_temperature     292(2)
_cell_special_details
;
;
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colorless'
_exptl_crystal_size_max     0.18
_exptl_crystal_size_mid     0.12
_exptl_crystal_size_min     0.08
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     1.464
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'Not Measured'
_exptl_crystal_F_000     1632
_exptl_absorpt_coefficient_mu     0.354
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction, 2009)
;
_exptl_absorpt_correction_T_min     0.9391
_exptl_absorpt_correction_T_max     0.9723
_exptl_special_details
;
;
_diffrn_ambient_temperature     292(2)
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_source     'Mova (Mo) X-ray Source'
_diffrn_radiation_monochromator     'mirror'
_diffrn_measurement_device_type     'Oxford Diffraction Xcalibur (Eos, Nova)'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     16.0839
_diffrn_reflns_number     36561
_diffrn_reflns_av_R_equivalents     0.0762
_diffrn_reflns_av_sigmaI/netI     0.0778
_diffrn_reflns_theta_min     2.65
_diffrn_reflns_theta_max     26.00
_diffrn_reflns_theta_full     26.00
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -24
_diffrn_reflns_limit_h_max     24
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -30
_diffrn_reflns_limit_l_max     30
_diffrn_reflns_reduction_process
;
;
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
2σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     7100
_reflns_number_gt     4182
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1125
_refine_ls_R_factor_gt     0.0531
_refine_ls_wR_factor_gt     0.0942
_refine_ls_wR_factor_ref     0.1181
_refine_ls_goodness_of_fit_ref     0.994
_refine_ls_restrained_S_all     0.994
_refine_ls_number_reflns     7100
_refine_ls_number_parameters     488
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0370P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.314
_refine_diff_density_min     -0.212
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0012(2)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details     'Flack (1983)'
_refine_ls_abs_structure_Flack     -0.05(8)
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'
_computing_data_collection
;
CrysAlis PRO (Oxford Diffraction, 2009)
;
_computing_cell_refinement
;
CrysAlis PRO (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis PRO (Oxford Diffraction, 2009)
;
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;ORTEP-3 for Windows (Farrugia, 2012)
 and Mercury (Macrae et al., 2008)
;
_computing_publication_material
                                'PLATON (Spek, 2009) and PARST (Nardelli, 1995)'
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S2 0.06104(6) 0.33720(18) 0.47599(5) 0.0583(4) Uani d . 1 1 . .
    S S1 0.17610(6) 0.63708(17) 0.25881(5) 0.0595(4) Uani d . 1 1 . .
    Cl Cl2 0.06464(8) 0.7998(2) 0.57593(6) 0.1029(6) Uani d . 1 1 . .
    Cl Cl1 0.18806(8) 0.1307(2) 0.15892(6) 0.1061(6) Uani d . 1 1 . .
    O O1 0.22799(14) 0.5887(4) 0.36472(11) 0.0561(8) Uani d . 1 1 . .
    N N1 0.08765(16) 0.8291(5) 0.31021(13) 0.0426(9) Uani d . 1 1 . .
    O O2 0.41192(16) 0.4498(5) 0.33659(13) 0.0686(10) Uani d . 1 1 . .
    O O3 0.00885(14) 0.3921(4) 0.37068(11) 0.0537(8) Uani d . 1 1 . .
    N N2 0.14867(17) 0.1432(5) 0.42445(14) 0.0442(9) Uani d . 1 1 . .
    F F1 0.37852(17) 0.3630(5) 0.53847(12) 0.1056(12) Uani d . 1 1 . .
    F F2 -0.14027(16) 0.6181(5) 0.19584(12) 0.0965(11) Uani d . 1 1 . .
    C C35 -0.0842(2) 0.5483(6) 0.33474(16) 0.0444(11) Uani d . 1 1 . .
    C C6 0.06876(18) 0.8298(5) 0.25537(18) 0.0420(10) Uani d . 1 1 . .
    C C27 0.1675(2) 0.1403(6) 0.47895(18) 0.0427(10) Uani d . 1 1 . .
    C C28 0.0952(2) 0.2386(5) 0.41793(18) 0.0406(10) Uani d . 1 1 . .
    C C16 0.3100(2) 0.3434(5) 0.29917(17) 0.0397(10) Uani d . 1 1 . .
    C C37 -0.0700(2) 0.6470(6) 0.43582(17) 0.0443(11) Uani d . 1 1 . .
    C C24 0.1953(2) 0.1670(7) 0.5891(2) 0.0622(14) Uani d . 1 1 . .
    H H24 0.2059 0.1769 0.6260 0.075 Uiso calc R 1 1 . .
    C C18 0.2180(2) 0.1664(6) 0.26527(19) 0.0530(12) Uani d . 1 1 . .
    H H18 0.1816 0.0900 0.2717 0.064 Uiso calc R 1 1 . .
    C C26 0.2223(2) 0.0503(6) 0.50034(18) 0.0532(12) Uani d . 1 1 . .
    H H26 0.2501 -0.0184 0.4779 0.064 Uiso calc R 1 1 . .
    C C34 -0.1231(2) 0.6039(6) 0.29010(19) 0.0553(13) Uani d . 1 1 . .
    H H34 -0.1627 0.6688 0.2955 0.066 Uiso calc R 1 1 . .
    C C9 0.2631(2) 0.5326(6) 0.40965(16) 0.0446(11) Uani d . 1 1 . .
    C C1 0.1111(2) 0.7311(6) 0.22139(19) 0.0492(12) Uani d . 1 1 . .
    C C19 0.2358(3) 0.2103(7) 0.21246(19) 0.0571(13) Uani d . 1 1 . .
    C C38 -0.0117(2) 0.7485(5) 0.4272(2) 0.0473(12) Uani d . 1 1 . .
    H H38 0.0004 0.7809 0.3918 0.057 Uiso calc R 1 1 . .
    C C15 0.3522(2) 0.4139(6) 0.34429(18) 0.0472(11) Uani d . 1 1 . .
    C C21 0.3291(2) 0.3796(6) 0.24532(17) 0.0500(12) Uani d . 1 1 . .
    H H21 0.3673 0.4487 0.2384 0.060 Uiso calc R 1 1 . .
    O O4 -0.17413(16) 0.5686(5) 0.39716(13) 0.0701(10) Uani d . 1 1 . .
    C C17 0.2540(2) 0.2356(6) 0.30809(19) 0.0461(12) Uani d . 1 1 . .
    H H17 0.2406 0.2100 0.3437 0.055 Uiso calc R 1 1 . .
    C C40 0.0101(3) 0.7524(7) 0.5223(2) 0.0609(14) Uani d . 1 1 . .
    C C2 0.0976(2) 0.7182(7) 0.1656(2) 0.0652(14) Uani d . 1 1 . .
    H H2 0.1258 0.6527 0.1427 0.078 Uiso calc R 1 1 . .
    C C10 0.2421(2) 0.5674(6) 0.46288(17) 0.0515(12) Uani d . 1 1 . .
    H H10 0.2019 0.6291 0.4693 0.062 Uiso calc R 1 1 . .
    C C41 -0.0482(2) 0.6569(7) 0.53269(19) 0.0623(14) Uani d . 1 1 . .
    H H41 -0.0604 0.6271 0.5682 0.075 Uiso calc R 1 1 . .
    C C32 -0.0457(3) 0.4639(7) 0.22913(18) 0.0631(14) Uani d . 1 1 . .
    H H32 -0.0333 0.4358 0.1935 0.076 Uiso calc R 1 1 . .
    C C29 0.0633(2) 0.2694(6) 0.36384(19) 0.0507(12) Uani d . 1 1 . .
    H H29A 0.0964 0.3179 0.3385 0.061 Uiso calc R 1 1 . .
    H H29B 0.0465 0.1574 0.3491 0.061 Uiso calc R 1 1 . .
    C C14 0.3237(2) 0.4423(6) 0.39979(17) 0.0426(11) Uani d . 1 1 . .
    C C5 0.0125(2) 0.9163(6) 0.23477(18) 0.0535(12) Uani d . 1 1 . .
    H H5 -0.0158 0.9825 0.2575 0.064 Uiso calc R 1 1 . .
    C C31 -0.0069(2) 0.4062(6) 0.27210(17) 0.0546(13) Uani d . 1 1 . .
    H H31 0.0321 0.3393 0.2658 0.066 Uiso calc R 1 1 . .
    C C22 0.1258(2) 0.2402(6) 0.51368(18) 0.0453(12) Uani d . 1 1 . .
    C C42 -0.0883(2) 0.6062(7) 0.48870(19) 0.0585(13) Uani d . 1 1 . .
    H H42 -0.1282 0.5435 0.4950 0.070 Uiso calc R 1 1 . .
    C C11 0.2812(3) 0.5095(6) 0.50601(18) 0.0633(14) Uani d . 1 1 . .
    H H11 0.2674 0.5295 0.5418 0.076 Uiso calc R 1 1 . .
    C C36 -0.1134(2) 0.5866(6) 0.39001(17) 0.0488(11) Uani d . 1 1 . .
    C C33 -0.1023(3) 0.5621(7) 0.2386(2) 0.0635(14) Uani d . 1 1 . .
    C C39 0.0280(2) 0.8013(6) 0.4703(2) 0.0546(12) Uani d . 1 1 . .
    H H39 0.0667 0.8696 0.4644 0.066 Uiso calc R 1 1 . .
    C C8 0.1729(2) 0.7062(6) 0.37194(18) 0.0504(12) Uani d . 1 1 . .
    H H8A 0.1884 0.8193 0.3868 0.061 Uiso calc R 1 1 . .
    H H8B 0.1401 0.6548 0.3969 0.061 Uiso calc R 1 1 . .
    C C30 -0.0263(2) 0.4483(6) 0.32504(18) 0.0458(11) Uani d . 1 1 . .
    C C4 -0.0004(2) 0.9022(7) 0.1803(2) 0.0667(15) Uani d . 1 1 . .
    H H4 -0.0384 0.9592 0.1659 0.080 Uiso calc R 1 1 . .
    C C7 0.1416(2) 0.7339(6) 0.31678(18) 0.0444(11) Uani d . 1 1 . .
    C C25 0.2354(2) 0.0638(7) 0.55564(19) 0.0610(13) Uani d . 1 1 . .
    H H25 0.2720 0.0021 0.5705 0.073 Uiso calc R 1 1 . .
    C C20 0.2919(2) 0.3138(6) 0.20268(19) 0.0574(13) Uani d . 1 1 . .
    H H20 0.3046 0.3394 0.1670 0.069 Uiso calc R 1 1 . .
    C C12 0.3407(3) 0.4220(7) 0.49521(19) 0.0641(14) Uani d . 1 1 . .
    C C13 0.3629(2) 0.3886(6) 0.4435(2) 0.0575(13) Uani d . 1 1 . .
    H H13 0.4039 0.3304 0.4378 0.069 Uiso calc R 1 1 . .
    C C23 0.1399(2) 0.2553(6) 0.5689(2) 0.0595(13) Uani d . 1 1 . .
    H H23 0.1124 0.3236 0.5917 0.071 Uiso calc R 1 1 . .
    C C3 0.0414(2) 0.8049(8) 0.1455(2) 0.0702(16) Uani d . 1 1 . .
    H H3 0.0314 0.7985 0.1085 0.084 Uiso calc R 1 1 . .
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell s.u.'s are taken into
account individually in the estimation of s.u.'s in distances, angles and
torsion angles; correlations between s.u.'s in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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
    S2 C22 . 1.735(4) ?
    S2 C28 . 1.737(4) ?
    S1 C1 . 1.726(4) ?
    S1 C7 . 1.733(4) ?
    Cl2 C40 . 1.734(5) ?
    Cl1 C19 . 1.721(5) ?
    O1 C9 . 1.366(5) ?
    O1 C8 . 1.408(4) ?
    N1 C7 . 1.291(5) ?
    N1 C6 . 1.393(5) ?
    O2 C15 . 1.224(5) ?
    O3 C30 . 1.380(5) ?
    O3 C29 . 1.422(5) ?
    N2 C28 . 1.283(5) ?
    N2 C27 . 1.386(5) ?
    F1 C12 . 1.369(5) ?
    F2 C33 . 1.354(5) ?
    C35 C30 . 1.387(6) ?
    C35 C34 . 1.398(5) ?
    C35 C36 . 1.498(6) ?
    C6 C5 . 1.380(5) ?
    C6 C1 . 1.391(6) ?
    C27 C26 . 1.376(5) ?
    C27 C22 . 1.399(5) ?
    C28 C29 . 1.485(6) ?
    C16 C17 . 1.385(5) ?
    C16 C21 . 1.398(6) ?
    C16 C15 . 1.480(6) ?
    C37 C42 . 1.378(6) ?
    C37 C38 . 1.394(5) ?
    C37 C36 . 1.481(6) ?
    C24 C23 . 1.369(6) ?
    C24 C25 . 1.376(6) ?
    C24 H24 . 0.9300 ?
    C18 C17 . 1.368(6) ?
    C18 C19 . 1.380(6) ?
    C18 H18 . 0.9300 ?
    C26 C25 . 1.382(6) ?
    C26 H26 . 0.9300 ?
    C34 C33 . 1.362(7) ?
    C34 H34 . 0.9300 ?
    C9 C10 . 1.392(5) ?
    C9 C14 . 1.394(6) ?
    C1 C2 . 1.395(6) ?
    C19 C20 . 1.371(6) ?
    C38 C39 . 1.373(6) ?
    C38 H38 . 0.9300 ?
    C15 C14 . 1.486(6) ?
    C21 C20 . 1.368(6) ?
    C21 H21 . 0.9300 ?
    O4 C36 . 1.218(5) ?
    C17 H17 . 0.9300 ?
    C40 C39 . 1.369(7) ?
    C40 C41 . 1.378(6) ?
    C2 C3 . 1.374(6) ?
    C2 H2 . 0.9300 ?
    C10 C11 . 1.378(6) ?
    C10 H10 . 0.9300 ?
    C41 C42 . 1.389(6) ?
    C41 H41 . 0.9300 ?
    C32 C33 . 1.356(7) ?
    C32 C31 . 1.371(6) ?
    C32 H32 . 0.9300 ?
    C29 H29A . 0.9700 ?
    C29 H29B . 0.9700 ?
    C14 C13 . 1.381(5) ?
    C5 C4 . 1.363(6) ?
    C5 H5 . 0.9300 ?
    C31 C30 . 1.388(5) ?
    C31 H31 . 0.9300 ?
    C22 C23 . 1.386(6) ?
    C42 H42 . 0.9300 ?
    C11 C12 . 1.369(7) ?
    C11 H11 . 0.9300 ?
    C39 H39 . 0.9300 ?
    C8 C7 . 1.500(6) ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
    C4 C3 . 1.391(6) ?
    C4 H4 . 0.9300 ?
    C25 H25 . 0.9300 ?
    C20 H20 . 0.9300 ?
    C12 C13 . 1.362(6) ?
    C13 H13 . 0.9300 ?
    C23 H23 . 0.9300 ?
    C3 H3 . 0.9300 ?
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
    C22 S2 C28 . . 88.4(2) ?
    C1 S1 C7 . . 88.4(2) ?
    C9 O1 C8 . . 118.8(3) ?
    C7 N1 C6 . . 110.0(3) ?
    C30 O3 C29 . . 118.7(3) ?
    C28 N2 C27 . . 110.4(3) ?
    C30 C35 C34 . . 118.6(4) ?
    C30 C35 C36 . . 125.0(4) ?
    C34 C35 C36 . . 116.1(4) ?
    C5 C6 N1 . . 124.7(4) ?
    C5 C6 C1 . . 120.9(4) ?
    N1 C6 C1 . . 114.5(4) ?
    C26 C27 N2 . . 125.8(4) ?
    C26 C27 C22 . . 119.4(4) ?
    N2 C27 C22 . . 114.8(4) ?
    N2 C28 C29 . . 123.1(4) ?
    N2 C28 S2 . . 116.9(3) ?
    C29 C28 S2 . . 120.0(3) ?
    C17 C16 C21 . . 118.5(4) ?
    C17 C16 C15 . . 122.5(4) ?
    C21 C16 C15 . . 118.9(4) ?
    C42 C37 C38 . . 118.6(4) ?
    C42 C37 C36 . . 119.5(4) ?
    C38 C37 C36 . . 121.9(4) ?
    C23 C24 C25 . . 121.1(5) ?
    C23 C24 H24 . . 119.5 ?
    C25 C24 H24 . . 119.5 ?
    C17 C18 C19 . . 119.7(4) ?
    C17 C18 H18 . . 120.1 ?
    C19 C18 H18 . . 120.1 ?
    C27 C26 C25 . . 119.0(4) ?
    C27 C26 H26 . . 120.5 ?
    C25 C26 H26 . . 120.5 ?
    C33 C34 C35 . . 119.4(4) ?
    C33 C34 H34 . . 120.3 ?
    C35 C34 H34 . . 120.3 ?
    O1 C9 C10 . . 123.1(4) ?
    O1 C9 C14 . . 116.4(4) ?
    C10 C9 C14 . . 120.5(4) ?
    C2 C1 C6 . . 120.5(4) ?
    C2 C1 S1 . . 129.3(4) ?
    C6 C1 S1 . . 110.2(3) ?
    C20 C19 C18 . . 120.3(4) ?
    C20 C19 Cl1 . . 120.3(4) ?
    C18 C19 Cl1 . . 119.5(4) ?
    C39 C38 C37 . . 120.7(5) ?
    C39 C38 H38 . . 119.7 ?
    C37 C38 H38 . . 119.7 ?
    O2 C15 C16 . . 120.3(4) ?
    O2 C15 C14 . . 118.3(4) ?
    C16 C15 C14 . . 121.4(4) ?
    C20 C21 C16 . . 120.4(4) ?
    C20 C21 H21 . . 119.8 ?
    C16 C21 H21 . . 119.8 ?
    C18 C17 C16 . . 120.9(4) ?
    C18 C17 H17 . . 119.6 ?
    C16 C17 H17 . . 119.6 ?
    C39 C40 C41 . . 121.7(5) ?
    C39 C40 Cl2 . . 119.3(4) ?
    C41 C40 Cl2 . . 118.9(4) ?
    C3 C2 C1 . . 118.2(5) ?
    C3 C2 H2 . . 120.9 ?
    C1 C2 H2 . . 120.9 ?
    C11 C10 C9 . . 119.5(4) ?
    C11 C10 H10 . . 120.3 ?
    C9 C10 H10 . . 120.3 ?
    C40 C41 C42 . . 118.2(4) ?
    C40 C41 H41 . . 120.9 ?
    C42 C41 H41 . . 120.9 ?
    C33 C32 C31 . . 119.9(4) ?
    C33 C32 H32 . . 120.0 ?
    C31 C32 H32 . . 120.0 ?
    O3 C29 C28 . . 108.4(4) ?
    O3 C29 H29A . . 110.0 ?
    C28 C29 H29A . . 110.0 ?
    O3 C29 H29B . . 110.0 ?
    C28 C29 H29B . . 110.0 ?
    H29A C29 H29B . . 108.4 ?
    C13 C14 C9 . . 119.2(4) ?
    C13 C14 C15 . . 117.1(4) ?
    C9 C14 C15 . . 123.5(4) ?
    C4 C5 C6 . . 118.2(5) ?
    C4 C5 H5 . . 120.9 ?
    C6 C5 H5 . . 120.9 ?
    C32 C31 C30 . . 119.5(4) ?
    C32 C31 H31 . . 120.3 ?
    C30 C31 H31 . . 120.3 ?
    C23 C22 C27 . . 121.3(4) ?
    C23 C22 S2 . . 129.2(4) ?
    C27 C22 S2 . . 109.5(3) ?
    C37 C42 C41 . . 121.3(4) ?
    C37 C42 H42 . . 119.4 ?
    C41 C42 H42 . . 119.4 ?
    C12 C11 C10 . . 118.8(4) ?
    C12 C11 H11 . . 120.6 ?
    C10 C11 H11 . . 120.6 ?
    O4 C36 C37 . . 119.6(4) ?
    O4 C36 C35 . . 119.1(4) ?
    C37 C36 C35 . . 121.4(4) ?
    F2 C33 C32 . . 119.4(5) ?
    F2 C33 C34 . . 118.6(5) ?
    C32 C33 C34 . . 122.0(4) ?
    C40 C39 C38 . . 119.4(4) ?
    C40 C39 H39 . . 120.3 ?
    C38 C39 H39 . . 120.3 ?
    O1 C8 C7 . . 106.9(3) ?
    O1 C8 H8A . . 110.3 ?
    C7 C8 H8A . . 110.3 ?
    O1 C8 H8B . . 110.3 ?
    C7 C8 H8B . . 110.3 ?
    H8A C8 H8B . . 108.6 ?
    O3 C30 C31 . . 123.3(4) ?
    O3 C30 C35 . . 116.1(4) ?
    C31 C30 C35 . . 120.6(4) ?
    C5 C4 C3 . . 121.9(5) ?
    C5 C4 H4 . . 119.0 ?
    C3 C4 H4 . . 119.0 ?
    N1 C7 C8 . . 121.9(4) ?
    N1 C7 S1 . . 116.9(3) ?
    C8 C7 S1 . . 121.2(3) ?
    C24 C25 C26 . . 121.0(4) ?
    C24 C25 H25 . . 119.5 ?
    C26 C25 H25 . . 119.5 ?
    C21 C20 C19 . . 120.2(4) ?
    C21 C20 H20 . . 119.9 ?
    C19 C20 H20 . . 119.9 ?
    C13 C12 F1 . . 119.0(5) ?
    C13 C12 C11 . . 122.9(4) ?
    F1 C12 C11 . . 118.2(5) ?
    C12 C13 C14 . . 119.1(4) ?
    C12 C13 H13 . . 120.4 ?
    C14 C13 H13 . . 120.4 ?
    C24 C23 C22 . . 118.1(4) ?
    C24 C23 H23 . . 120.9 ?
    C22 C23 H23 . . 120.9 ?
    C2 C3 C4 . . 120.4(5) ?
    C2 C3 H3 . . 119.8 ?
    C4 C3 H3 . . 119.8 ?
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
    C7 N1 C6 C5 . . . . 178.7(4) ?
    C7 N1 C6 C1 . . . . -0.1(5) ?
    C28 N2 C27 C26 . . . . 179.8(4) ?
    C28 N2 C27 C22 . . . . -0.5(5) ?
    C27 N2 C28 C29 . . . . 179.1(4) ?
    C27 N2 C28 S2 . . . . 0.2(5) ?
    C22 S2 C28 N2 . . . . 0.1(3) ?
    C22 S2 C28 C29 . . . . -178.8(4) ?
    N2 C27 C26 C25 . . . . 178.5(4) ?
    C22 C27 C26 C25 . . . . -1.2(6) ?
    C30 C35 C34 C33 . . . . -1.4(7) ?
    C36 C35 C34 C33 . . . . -175.2(4) ?
    C8 O1 C9 C10 . . . . 8.4(6) ?
    C8 O1 C9 C14 . . . . -169.3(4) ?
    C5 C6 C1 C2 . . . . 0.2(7) ?
    N1 C6 C1 C2 . . . . 179.1(4) ?
    C5 C6 C1 S1 . . . . -179.3(3) ?
    N1 C6 C1 S1 . . . . -0.4(5) ?
    C7 S1 C1 C2 . . . . -178.8(5) ?
    C7 S1 C1 C6 . . . . 0.6(3) ?
    C17 C18 C19 C20 . . . . 4.0(7) ?
    C17 C18 C19 Cl1 . . . . -177.1(4) ?
    C42 C37 C38 C39 . . . . 2.3(6) ?
    C36 C37 C38 C39 . . . . -179.4(4) ?
    C17 C16 C15 O2 . . . . 153.1(4) ?
    C21 C16 C15 O2 . . . . -23.8(6) ?
    C17 C16 C15 C14 . . . . -26.6(6) ?
    C21 C16 C15 C14 . . . . 156.5(4) ?
    C17 C16 C21 C20 . . . . 1.9(6) ?
    C15 C16 C21 C20 . . . . 178.9(4) ?
    C19 C18 C17 C16 . . . . -2.8(7) ?
    C21 C16 C17 C18 . . . . -0.1(6) ?
    C15 C16 C17 C18 . . . . -177.1(4) ?
    C6 C1 C2 C3 . . . . -0.2(7) ?
    S1 C1 C2 C3 . . . . 179.2(4) ?
    O1 C9 C10 C11 . . . . -178.5(4) ?
    C14 C9 C10 C11 . . . . -0.9(7) ?
    C39 C40 C41 C42 . . . . 1.7(7) ?
    Cl2 C40 C41 C42 . . . . -174.4(4) ?
    C30 O3 C29 C28 . . . . 176.6(3) ?
    N2 C28 C29 O3 . . . . -175.2(4) ?
    S2 C28 C29 O3 . . . . 3.6(5) ?
    O1 C9 C14 C13 . . . . 177.4(4) ?
    C10 C9 C14 C13 . . . . -0.4(7) ?
    O1 C9 C14 C15 . . . . 3.1(6) ?
    C10 C9 C14 C15 . . . . -174.7(4) ?
    O2 C15 C14 C13 . . . . -43.0(6) ?
    C16 C15 C14 C13 . . . . 136.7(4) ?
    O2 C15 C14 C9 . . . . 131.3(5) ?
    C16 C15 C14 C9 . . . . -49.0(6) ?
    N1 C6 C5 C4 . . . . -178.7(4) ?
    C1 C6 C5 C4 . . . . 0.1(7) ?
    C33 C32 C31 C30 . . . . 0.3(7) ?
    C26 C27 C22 C23 . . . . 2.2(6) ?
    N2 C27 C22 C23 . . . . -177.5(4) ?
    C26 C27 C22 S2 . . . . -179.7(3) ?
    N2 C27 C22 S2 . . . . 0.6(5) ?
    C28 S2 C22 C23 . . . . 177.5(5) ?
    C28 S2 C22 C27 . . . . -0.4(3) ?
    C38 C37 C42 C41 . . . . -3.1(7) ?
    C36 C37 C42 C41 . . . . 178.5(4) ?
    C40 C41 C42 C37 . . . . 1.2(7) ?
    C9 C10 C11 C12 . . . . 1.2(7) ?
    C42 C37 C36 O4 . . . . 29.3(6) ?
    C38 C37 C36 O4 . . . . -148.9(4) ?
    C42 C37 C36 C35 . . . . -151.1(4) ?
    C38 C37 C36 C35 . . . . 30.6(6) ?
    C30 C35 C36 O4 . . . . -134.0(5) ?
    C34 C35 C36 O4 . . . . 39.3(6) ?
    C30 C35 C36 C37 . . . . 46.5(7) ?
    C34 C35 C36 C37 . . . . -140.2(4) ?
    C31 C32 C33 F2 . . . . -179.9(4) ?
    C31 C32 C33 C34 . . . . -1.1(8) ?
    C35 C34 C33 F2 . . . . -179.5(4) ?
    C35 C34 C33 C32 . . . . 1.7(8) ?
    C41 C40 C39 C38 . . . . -2.4(7) ?
    Cl2 C40 C39 C38 . . . . 173.6(3) ?
    C37 C38 C39 C40 . . . . 0.4(7) ?
    C9 O1 C8 C7 . . . . -176.1(4) ?
    C29 O3 C30 C31 . . . . -6.9(6) ?
    C29 O3 C30 C35 . . . . 171.6(4) ?
    C32 C31 C30 O3 . . . . 178.4(4) ?
    C32 C31 C30 C35 . . . . -0.1(7) ?
    C34 C35 C30 O3 . . . . -177.9(4) ?
    C36 C35 C30 O3 . . . . -4.8(6) ?
    C34 C35 C30 C31 . . . . 0.7(6) ?
    C36 C35 C30 C31 . . . . 173.9(4) ?
    C6 C5 C4 C3 . . . . -0.4(7) ?
    C6 N1 C7 C8 . . . . -178.8(4) ?
    C6 N1 C7 S1 . . . . 0.6(5) ?
    O1 C8 C7 N1 . . . . 176.7(4) ?
    O1 C8 C7 S1 . . . . -2.7(5) ?
    C1 S1 C7 N1 . . . . -0.8(4) ?
    C1 S1 C7 C8 . . . . 178.7(4) ?
    C23 C24 C25 C26 . . . . 2.0(8) ?
    C27 C26 C25 C24 . . . . -0.9(7) ?
    C16 C21 C20 C19 . . . . -0.7(7) ?
    C18 C19 C20 C21 . . . . -2.3(7) ?
    Cl1 C19 C20 C21 . . . . 178.9(4) ?
    C10 C11 C12 C13 . . . . -0.3(8) ?
    C10 C11 C12 F1 . . . . -179.1(4) ?
    F1 C12 C13 C14 . . . . 177.7(4) ?
    C11 C12 C13 C14 . . . . -1.0(8) ?
    C9 C14 C13 C12 . . . . 1.4(7) ?
    C15 C14 C13 C12 . . . . 176.0(4) ?
    C25 C24 C23 C22 . . . . -0.9(7) ?
    C27 C22 C23 C24 . . . . -1.1(7) ?
    S2 C22 C23 C24 . . . . -178.9(4) ?
    C1 C2 C3 C4 . . . . -0.1(8) ?
    C5 C4 C3 C2 . . . . 0.4(8) ?
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
    C3 H3 F1 3_554 0.93 2.52 3.091(6) 120 yes
    C5 H5 O2 4_465 0.93 2.46 3.340(5) 158 yes
    C26 H26 O4 4_555 0.93 2.51 3.369(5) 154 yes
    C18 H18 Cg1 1_545 0.93 2.83 3.686(5) 154 yes
    C39 H39 Cg2 1_565 0.93 2.82 3.619(5) 145 yes
