data_global
_audit_creation_method                  'APEX3 v2018.1-0'

_publ_requested_journal                 ?

_publ_contact_author_name               ?
_publ_contact_author_address            
;
;
_publ_contact_author_email              ?
_publ_contact_author_fax                ?
_publ_contact_author_phone              ?

_publ_section_title                     
;
;
_publ_section_abstract                  
;
;
_publ_section_references                
;
;
_publ_section_comment                   
;
;

data_20190225WP5_66_3
_chemical_name_systematic               ?
_chemical_name_common                   ?
_chemical_formula_moiety               'C24 H20 Cl2 O4 S'
_chemical_formula_sum                   'C24 H20 Cl2 O4 S'
_chemical_formula_iupac                 ?
_chemical_formula_weight                475.36

_chemical_melting_point                 ?

_space_group_crystal_system             triclinic
_space_group_name_H-M_alt               'P -1'
_space_group_name_Hall                  '-P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, -z'

_cell_length_a                          8.3310(14)
_cell_length_b                          11.3580(19)
_cell_length_c                          12.437(2)
_cell_angle_alpha                       95.499(5)
_cell_angle_beta                        103.944(5)
_cell_angle_gamma                       90.227(5)
_cell_volume                            1136.5(3)
_cell_formula_units_Z                   2
_cell_measurement_reflns_used           9471
_cell_measurement_theta_min             3.9115
_cell_measurement_theta_max             74.1444
_cell_measurement_temperature           206.(2)

_exptl_crystal_description              block
_exptl_crystal_colour                   'clear light colourless'
_exptl_crystal_size_max                 0.150
_exptl_crystal_size_mid                 0.120
_exptl_crystal_size_min                 0.100
_exptl_crystal_density_diffrn           1.389
_exptl_crystal_density_meas             ?
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    492

_exptl_absorpt_coefficient_mu           3.667
_exptl_absorpt_correction_type          Multi-Scan
_exptl_absorpt_process_details          
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min         0.55
_exptl_absorpt_correction_T_max         0.71

_exptl_special_details                  
;
; 

_diffrn_ambient_temperature             206.(2)

_diffrn_source                          ?
_diffrn_source_type                     ?

_diffrn_radiation_type                  'cu k\a'
_diffrn_radiation_wavelength            1.54178
_diffrn_radiation_monochromator         ?

_diffrn_measurement_device_type         'd8 venture'
_diffrn_measurement_method              ?

_diffrn_detector_area_resol_mean        7.3910

_diffrn_reflns_number                   24304
_diffrn_reflns_av_R_equivalents         0.0470
_diffrn_reflns_av_unetI/netI            0.0661
_diffrn_reflns_theta_min                3.91
_diffrn_reflns_theta_max                74.57
_diffrn_reflns_theta_full               74.57
_diffrn_measured_fraction_theta_max     0.954
_diffrn_measured_fraction_theta_full    0.954
_diffrn_reflns_limit_h_min              -10
_diffrn_reflns_limit_h_max              10
_diffrn_reflns_limit_k_min              -13
_diffrn_reflns_limit_k_max              14
_diffrn_reflns_limit_l_min              -15
_diffrn_reflns_limit_l_max              15

_refine_special_details                 
;
;

_reflns_number_total                    4448
_reflns_number_gt                       3530
_reflns_threshold_expression            'I > 2σ(I)'

_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.1173
_refine_ls_R_factor_gt                  0.0436
_refine_ls_wR_factor_gt                 0.1251
_refine_ls_wR_factor_ref                0.1637
_refine_ls_goodness_of_fit_ref          1.264
_refine_ls_restrained_S_all             1.264
_refine_ls_number_reflns                4448
_refine_ls_number_parameters            282
_refine_ls_number_restraints            0
_refine_ls_number_constraints           ?
_refine_ls_hydrogen_treatment           constr
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details            
    'w=1/[σ²(Fo²)+(0.0735P)²+0.3830P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens          geom
_atom_sites_solution_primary            ?
_atom_sites_solution_secondary          ?

_refine_ls_shift/su_max                 0.001
_refine_ls_shift/su_mean                0.000
_refine_diff_density_max                0.769
_refine_diff_density_min                -0.708
_refine_ls_extinction_method            none
_refine_ls_extinction_coef              ?

loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C C 0.0181 0.0091 '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'
    O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    Cl Cl 0.3639 0.7018
     'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection              ?
_computing_cell_refinement              'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction               'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution           'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement         'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics           'shelXle (C.B. Huebschle, rev 882)'
_computing_publication_material         ?

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_adp
    _atom_site_refinement_flags_occupancy
    _atom_site_refinement_flags_posn
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cl Cl1 0.80894(11) 1.09052(10) 0.02064(8) 0.0895(3) Uani d . . . 1 . .
    Cl Cl2 0.75598(10) 0.40175(8) -0.02299(6) 0.0718(3) Uani d . . . 1 . .
    S S1 0.58870(7) 0.62087(6) 0.47495(5) 0.0496(2) Uani d . . . 1 . .
    O O1 0.9211(2) 0.83138(18) 0.51295(15) 0.0516(5) Uani d . . . 1 . .
    O O2 0.9642(2) 0.63891(17) 0.48203(15) 0.0540(5) Uani d . . . 1 . .
    O O3 0.35988(19) 0.90595(18) 0.37927(16) 0.0543(5) Uani d . . . 1 . .
    O O4 0.3443(2) 0.73487(19) 0.27246(17) 0.0601(5) Uani d . . . 1 . .
    C C1 0.7555(3) 1.0134(3) 0.1224(2) 0.0545(7) Uani d . . . 1 . .
    C C2 0.6459(3) 0.9182(3) 0.0886(2) 0.0539(7) Uani d . . . 1 . .
    H H2 0.60165 0.895341 0.012457 0.065 Uiso calc U . R 1 . .
    C C3 0.6022(3) 0.8570(3) 0.1682(2) 0.0473(6) Uani d . . . 1 . .
    H H20 0.528598 0.791394 0.145818 0.057 Uiso calc U . R 1 . .
    C C4 0.6655(2) 0.8908(2) 0.28170(19) 0.0398(5) Uani d . . . 1 . .
    C C5 0.6127(2) 0.8249(2) 0.36919(18) 0.0386(5) Uani d . . . 1 . .
    H H16 0.640739 0.877454 0.439699 0.046 Uiso calc U . R 1 . .
    C C6 0.7005(3) 0.7063(2) 0.39322(18) 0.0382(5) Uani d . . . 1 . .
    C C7 0.6611(3) 0.6855(3) 0.6145(2) 0.0480(6) Uani d . . . 1 . .
    C C8 0.5934(3) 0.7871(3) 0.6533(2) 0.0586(7) Uani d . . . 1 . .
    H H5 0.510782 0.825591 0.604617 0.07 Uiso calc U . R 1 . .
    C C9 0.6470(4) 0.8323(4) 0.7635(3) 0.0723(9) Uani d . . . 1 . .
    H H8 0.600748 0.901441 0.789502 0.087 Uiso calc U . R 1 . .
    C C10 0.7667(4) 0.7769(4) 0.8347(3) 0.0765(10) Uani d . . . 1 . .
    H H1 0.804395 0.808786 0.909236 0.092 Uiso calc U . R 1 . .
    C C11 0.7748(3) 0.9880(2) 0.3127(2) 0.0468(6) Uani d . . . 1 . .
    H H4 0.818331 1.012293 0.388578 0.056 Uiso calc U . R 1 . .
    C C12 0.8204(3) 1.0494(3) 0.2331(2) 0.0544(7) Uani d . . . 1 . .
    H H3 0.894765 1.114661 0.254645 0.065 Uiso calc U . R 1 . .
    C C13 0.8323(4) 0.6743(4) 0.7974(3) 0.0792(11) Uani d . . . 1 . .
    H H7 0.912936 0.635395 0.847194 0.095 Uiso calc U . R 1 . .
    C C14 0.7803(4) 0.6279(3) 0.6870(2) 0.0645(8) Uani d . . . 1 . .
    H H6 0.825638 0.558017 0.661735 0.077 Uiso calc U . R 1 . .
    C C15 0.8740(3) 0.7348(2) 0.46897(18) 0.0410(5) Uani d . . . 1 . .
    C C16 1.1290(4) 0.6548(3) 0.5542(3) 0.0715(9) Uani d . . . 1 . .
    H H10 1.187781 0.717522 0.530433 0.107 Uiso calc U . R 1 . .
    H H9 1.18813 0.581792 0.550169 0.107 Uiso calc U . R 1 . .
    H H11 1.121444 0.675904 0.630191 0.107 Uiso calc U . R 1 . .
    C C17 0.7118(3) 0.6260(2) 0.28952(18) 0.0398(5) Uani d . . . 1 . .
    C C18 0.8394(3) 0.6454(3) 0.2384(2) 0.0502(6) Uani d . . . 1 . .
    H H15 0.918115 0.706424 0.269571 0.06 Uiso calc U . R 1 . .
    C C19 0.8539(3) 0.5777(3) 0.1432(2) 0.0563(7) Uani d . . . 1 . .
    H H12 0.940502 0.593028 0.109609 0.068 Uiso calc U . R 1 . .
    C C20 0.7396(3) 0.4871(3) 0.0980(2) 0.0518(6) Uani d . . . 1 . .
    C C21 0.6120(3) 0.4653(3) 0.1459(2) 0.0553(7) Uani d . . . 1 . .
    H H14 0.534521 0.403536 0.114563 0.066 Uiso calc U . R 1 . .
    C C22 0.5978(3) 0.5349(3) 0.2413(2) 0.0478(6) Uani d . . . 1 . .
    H H13 0.509706 0.520133 0.273649 0.057 Uiso calc U . R 1 . .
    C C23 0.4246(3) 0.8114(2) 0.33458(18) 0.0413(5) Uani d . . . 1 . .
    C C24 0.1829(3) 0.9165(3) 0.3413(3) 0.0687(9) Uani d . . . 1 . .
    H H18 0.151781 0.908577 0.26054 0.103 Uiso calc U . R 1 . .
    H H17 0.150973 0.993328 0.369229 0.103 Uiso calc U . R 1 . .
    H H19 0.127283 0.854797 0.368585 0.103 Uiso calc U . R 1 . .


_geom_special_details                   
;

All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds 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
    Cl1 C1 . 1.745(3) ?
    Cl2 C20 . 1.744(3) ?
    S1 C7 . 1.778(3) ?
    S1 C6 . 1.865(2) ?
    O1 C15 . 1.198(3) ?
    O2 C15 . 1.326(3) ?
    O2 C16 . 1.447(3) ?
    O3 C23 . 1.337(3) ?
    O3 C24 . 1.445(3) ?
    O4 C23 . 1.191(3) ?
    C1 C12 . 1.374(4) ?
    C1 C2 . 1.379(4) ?
    C2 C3 . 1.379(4) ?
    C2 H2 . 0.94 ?
    C3 C4 . 1.397(3) ?
    C3 H20 . 0.94 ?
    C4 C11 . 1.392(3) ?
    C4 C5 . 1.524(3) ?
    C5 C23 . 1.524(3) ?
    C5 C6 . 1.555(3) ?
    C5 H16 . 0.99 ?
    C6 C17 . 1.529(3) ?
    C6 C15 . 1.538(3) ?
    C7 C8 . 1.383(4) ?
    C7 C14 . 1.384(4) ?
    C8 C9 . 1.382(4) ?
    C8 H5 . 0.94 ?
    C9 C10 . 1.364(5) ?
    C9 H8 . 0.94 ?
    C10 C13 . 1.377(5) ?
    C10 H1 . 0.94 ?
    C11 C12 . 1.386(4) ?
    C11 H4 . 0.94 ?
    C12 H3 . 0.94 ?
    C13 C14 . 1.387(5) ?
    C13 H7 . 0.94 ?
    C14 H6 . 0.94 ?
    C16 H10 . 0.97 ?
    C16 H9 . 0.97 ?
    C16 H11 . 0.97 ?
    C17 C22 . 1.389(3) ?
    C17 C18 . 1.391(3) ?
    C18 C19 . 1.379(4) ?
    C18 H15 . 0.94 ?
    C19 C20 . 1.380(4) ?
    C19 H12 . 0.94 ?
    C20 C21 . 1.371(4) ?
    C21 C22 . 1.391(4) ?
    C21 H14 . 0.94 ?
    C22 H13 . 0.94 ?
    C24 H18 . 0.97 ?
    C24 H17 . 0.97 ?
    C24 H19 . 0.97 ?

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
    C7 S1 C6 . . 104.45(11) ?
    C15 O2 C16 . . 116.6(2) ?
    C23 O3 C24 . . 116.0(2) ?
    C12 C1 C2 . . 121.6(2) ?
    C12 C1 Cl1 . . 119.9(2) ?
    C2 C1 Cl1 . . 118.5(2) ?
    C3 C2 C1 . . 118.9(2) ?
    C3 C2 H2 . . 120.5 ?
    C1 C2 H2 . . 120.5 ?
    C2 C3 C4 . . 121.2(2) ?
    C2 C3 H20 . . 119.4 ?
    C4 C3 H20 . . 119.4 ?
    C11 C4 C3 . . 118.2(2) ?
    C11 C4 C5 . . 120.9(2) ?
    C3 C4 C5 . . 120.8(2) ?
    C4 C5 C23 . . 107.03(18) ?
    C4 C5 C6 . . 115.30(17) ?
    C23 C5 C6 . . 113.4(2) ?
    C4 C5 H16 . . 106.9 ?
    C23 C5 H16 . . 106.9 ?
    C6 C5 H16 . . 106.9 ?
    C17 C6 C15 . . 110.41(18) ?
    C17 C6 C5 . . 114.74(18) ?
    C15 C6 C5 . . 108.31(19) ?
    C17 C6 S1 . . 107.57(16) ?
    C15 C6 S1 . . 105.85(15) ?
    C5 C6 S1 . . 109.59(14) ?
    C8 C7 C14 . . 119.7(3) ?
    C8 C7 S1 . . 121.5(2) ?
    C14 C7 S1 . . 118.7(2) ?
    C9 C8 C7 . . 120.2(3) ?
    C9 C8 H5 . . 119.9 ?
    C7 C8 H5 . . 119.9 ?
    C10 C9 C8 . . 120.3(3) ?
    C10 C9 H8 . . 119.9 ?
    C8 C9 H8 . . 119.9 ?
    C9 C10 C13 . . 120.0(3) ?
    C9 C10 H1 . . 120.0 ?
    C13 C10 H1 . . 120.0 ?
    C12 C11 C4 . . 120.9(2) ?
    C12 C11 H4 . . 119.5 ?
    C4 C11 H4 . . 119.5 ?
    C1 C12 C11 . . 119.1(3) ?
    C1 C12 H3 . . 120.5 ?
    C11 C12 H3 . . 120.5 ?
    C10 C13 C14 . . 120.5(3) ?
    C10 C13 H7 . . 119.8 ?
    C14 C13 H7 . . 119.8 ?
    C7 C14 C13 . . 119.4(3) ?
    C7 C14 H6 . . 120.3 ?
    C13 C14 H6 . . 120.3 ?
    O1 C15 O2 . . 124.0(2) ?
    O1 C15 C6 . . 124.2(2) ?
    O2 C15 C6 . . 111.8(2) ?
    O2 C16 H10 . . 109.5 ?
    O2 C16 H9 . . 109.5 ?
    H10 C16 H9 . . 109.5 ?
    O2 C16 H11 . . 109.5 ?
    H10 C16 H11 . . 109.5 ?
    H9 C16 H11 . . 109.5 ?
    C22 C17 C18 . . 117.5(2) ?
    C22 C17 C6 . . 123.2(2) ?
    C18 C17 C6 . . 119.3(2) ?
    C19 C18 C17 . . 122.0(2) ?
    C19 C18 H15 . . 119.0 ?
    C17 C18 H15 . . 119.0 ?
    C18 C19 C20 . . 119.1(2) ?
    C18 C19 H12 . . 120.4 ?
    C20 C19 H12 . . 120.4 ?
    C21 C20 C19 . . 120.7(2) ?
    C21 C20 Cl2 . . 119.9(2) ?
    C19 C20 Cl2 . . 119.4(2) ?
    C20 C21 C22 . . 119.7(3) ?
    C20 C21 H14 . . 120.2 ?
    C22 C21 H14 . . 120.2 ?
    C17 C22 C21 . . 121.1(2) ?
    C17 C22 H13 . . 119.5 ?
    C21 C22 H13 . . 119.5 ?
    O4 C23 O3 . . 123.8(2) ?
    O4 C23 C5 . . 127.3(2) ?
    O3 C23 C5 . . 108.7(2) ?
    O3 C24 H18 . . 109.5 ?
    O3 C24 H17 . . 109.5 ?
    H18 C24 H17 . . 109.5 ?
    O3 C24 H19 . . 109.5 ?
    H18 C24 H19 . . 109.5 ?
    H17 C24 H19 . . 109.5 ?

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
    C12 C1 C2 C3 . . . . -0.7(4) ?
    Cl1 C1 C2 C3 . . . . -179.7(2) ?
    C1 C2 C3 C4 . . . . 0.8(4) ?
    C2 C3 C4 C11 . . . . -0.3(4) ?
    C2 C3 C4 C5 . . . . 178.2(2) ?
    C11 C4 C5 C23 . . . . 131.1(2) ?
    C3 C4 C5 C23 . . . . -47.3(3) ?
    C11 C4 C5 C6 . . . . -101.8(3) ?
    C3 C4 C5 C6 . . . . 79.8(3) ?
    C4 C5 C6 C17 . . . . -45.6(3) ?
    C23 C5 C6 C17 . . . . 78.3(2) ?
    C4 C5 C6 C15 . . . . 78.3(2) ?
    C23 C5 C6 C15 . . . . -157.87(18) ?
    C4 C5 C6 S1 . . . . -166.69(15) ?
    C23 C5 C6 S1 . . . . -42.8(2) ?
    C7 S1 C6 C17 . . . . 153.89(15) ?
    C7 S1 C6 C15 . . . . 35.85(19) ?
    C7 S1 C6 C5 . . . . -80.75(17) ?
    C6 S1 C7 C8 . . . . 83.0(2) ?
    C6 S1 C7 C14 . . . . -101.2(2) ?
    C14 C7 C8 C9 . . . . 1.3(4) ?
    S1 C7 C8 C9 . . . . 177.0(2) ?
    C7 C8 C9 C10 . . . . -0.1(5) ?
    C8 C9 C10 C13 . . . . -1.3(6) ?
    C3 C4 C11 C12 . . . . -0.3(4) ?
    C5 C4 C11 C12 . . . . -178.7(2) ?
    C2 C1 C12 C11 . . . . 0.2(4) ?
    Cl1 C1 C12 C11 . . . . 179.2(2) ?
    C4 C11 C12 C1 . . . . 0.3(4) ?
    C9 C10 C13 C14 . . . . 1.5(6) ?
    C8 C7 C14 C13 . . . . -1.1(5) ?
    S1 C7 C14 C13 . . . . -177.0(3) ?
    C10 C13 C14 C7 . . . . -0.3(6) ?
    C16 O2 C15 O1 . . . . -0.1(4) ?
    C16 O2 C15 C6 . . . . -178.5(2) ?
    C17 C6 C15 O1 . . . . 135.7(2) ?
    C5 C6 C15 O1 . . . . 9.3(3) ?
    S1 C6 C15 O1 . . . . -108.2(2) ?
    C17 C6 C15 O2 . . . . -45.8(3) ?
    C5 C6 C15 O2 . . . . -172.24(18) ?
    S1 C6 C15 O2 . . . . 70.3(2) ?
    C15 C6 C17 C22 . . . . 142.1(2) ?
    C5 C6 C17 C22 . . . . -95.2(3) ?
    S1 C6 C17 C22 . . . . 27.0(3) ?
    C15 C6 C17 C18 . . . . -39.4(3) ?
    C5 C6 C17 C18 . . . . 83.3(3) ?
    S1 C6 C17 C18 . . . . -154.4(2) ?
    C22 C17 C18 C19 . . . . 0.1(4) ?
    C6 C17 C18 C19 . . . . -178.5(2) ?
    C17 C18 C19 C20 . . . . -0.7(4) ?
    C18 C19 C20 C21 . . . . 0.8(4) ?
    C18 C19 C20 Cl2 . . . . 179.5(2) ?
    C19 C20 C21 C22 . . . . -0.1(4) ?
    Cl2 C20 C21 C22 . . . . -178.9(2) ?
    C18 C17 C22 C21 . . . . 0.5(4) ?
    C6 C17 C22 C21 . . . . 179.1(2) ?
    C20 C21 C22 C17 . . . . -0.5(4) ?
    C24 O3 C23 O4 . . . . -4.7(4) ?
    C24 O3 C23 C5 . . . . 170.9(2) ?
    C4 C5 C23 O4 . . . . 86.2(3) ?
    C6 C5 C23 O4 . . . . -42.1(3) ?
    C4 C5 C23 O3 . . . . -89.2(2) ?
    C6 C5 C23 O3 . . . . 142.5(2) ?



