# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_70517b
_audit_block_doi                 10.5517/ccdc.csd.cc1p3jx7
_database_code_depnum_ccdc_archive 'CCDC 1552539'
_audit_update_record             
;
2017-05-26 deposited with the CCDC.
2017-09-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H19 Cl3 O5 S'
_chemical_formula_weight         537.81

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'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   9.7739(15)
_cell_length_b                   19.254(3)
_cell_length_c                   25.444(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4788.2(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    6096
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      26.40

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_F_000             2208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.506
_shelx_estimated_absorpt_T_min   0.823
_shelx_estimated_absorpt_T_max   0.951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.834
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32664
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.115
_diffrn_reflns_theta_max         27.342
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5402
_reflns_number_gt                3846
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0488P)²+3.3088P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5402
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1138
_refine_ls_wR_factor_gt          0.0998
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.69249(5) 0.12512(3) 0.74168(2) 0.02333(13) Uani 1 1 d . . . . .
Cl1 Cl 0.24680(11) 0.10032(5) 1.02580(3) 0.0731(3) Uani 1 1 d . . . . .
O1 O 0.74197(16) 0.05639(7) 0.73068(6) 0.0293(3) Uani 1 1 d . . . . .
O2 O 0.79343(16) 0.17843(8) 0.75078(6) 0.0332(4) Uani 1 1 d . . . . .
O3 O 0.45913(17) 0.19284(7) 0.86022(6) 0.0309(4) Uani 1 1 d . . . . .
O4 O 0.55241(17) 0.24424(7) 0.79207(6) 0.0319(4) Uani 1 1 d . . . . .
O5 O 0.5110(2) 0.02793(9) 0.58630(7) 0.0466(5) Uani 1 1 d . . . . .
C1 C 0.5349(2) 0.19043(10) 0.81478(8) 0.0252(4) Uani 1 1 d . . . . .
C2 C 0.5850(2) 0.12180(10) 0.79820(8) 0.0214(4) Uani 1 1 d . . . . .
C3 C 0.5591(2) 0.06336(10) 0.82651(8) 0.0216(4) Uani 1 1 d . . . . .
C4 C 0.4824(2) 0.06988(10) 0.87501(8) 0.0246(4) Uani 1 1 d . . . . .
C5 C 0.4512(3) 0.01365(12) 0.90811(9) 0.0325(5) Uani 1 1 d . . . . .
H5 H 0.4801 -0.0312 0.8988 0.039 Uiso 1 1 calc R U . . .
C6 C 0.3790(3) 0.02317(13) 0.95392(9) 0.0385(6) Uani 1 1 d . . . . .
H6 H 0.3587 -0.0149 0.9757 0.046 Uiso 1 1 calc R U . . .
C7 C 0.3365(3) 0.08925(14) 0.96773(9) 0.0413(6) Uani 1 1 d . . . . .
C8 C 0.3631(3) 0.14621(13) 0.93661(9) 0.0386(6) Uani 1 1 d . . . . .
H8 H 0.3329 0.1908 0.9462 0.046 Uiso 1 1 calc R U . . .
C9 C 0.4363(2) 0.13531(11) 0.89060(8) 0.0283(5) Uani 1 1 d . . . . .
C10 C 0.6025(2) -0.00843(10) 0.81160(8) 0.0224(4) Uani 1 1 d . . . . .
C11 C 0.5249(2) -0.04634(11) 0.77598(8) 0.0279(5) Uani 1 1 d . . . . .
H11 H 0.4475 -0.0263 0.7602 0.033 Uiso 1 1 calc R U . . .
C12 C 0.5621(3) -0.11377(11) 0.76375(9) 0.0349(5) Uani 1 1 d . . . . .
H12 H 0.5096 -0.1395 0.7397 0.042 Uiso 1 1 calc R U . . .
C13 C 0.6765(3) -0.14352(11) 0.78688(9) 0.0349(6) Uani 1 1 d . . . . .
H13 H 0.7024 -0.1891 0.7780 0.042 Uiso 1 1 calc R U . . .
C14 C 0.7527(3) -0.10614(11) 0.82302(9) 0.0343(5) Uani 1 1 d . . . . .
H14 H 0.8298 -0.1264 0.8389 0.041 Uiso 1 1 calc R U . . .
C15 C 0.7151(2) -0.03896(11) 0.83565(9) 0.0286(5) Uani 1 1 d . . . . .
H15 H 0.7659 -0.0138 0.8606 0.034 Uiso 1 1 calc R U . . .
C16 C 0.5881(2) 0.15361(11) 0.68884(8) 0.0272(5) Uani 1 1 d . . . . .
H16A H 0.5302 0.1917 0.7013 0.033 Uiso 1 1 calc R U . . .
H16B H 0.6474 0.1722 0.6611 0.033 Uiso 1 1 calc R U . . .
C17 C 0.5750(3) 0.03851(13) 0.63685(9) 0.0362(6) Uani 1 1 d . . . . .
H17A H 0.6714 0.0511 0.6323 0.043 Uiso 1 1 calc R U . . .
H17B H 0.5704 -0.0042 0.6578 0.043 Uiso 1 1 calc R U . . .
C18 C 0.4968(2) 0.09802(11) 0.66503(8) 0.0272(5) Uani 1 1 d . . . . .
H18 H 0.4361 0.0785 0.6924 0.033 Uiso 1 1 calc R U . . .
C19 C 0.4118(2) 0.12675(12) 0.62032(9) 0.0296(5) Uani 1 1 d . . . . .
C20 C 0.3297(2) 0.18480(13) 0.61694(10) 0.0358(5) Uani 1 1 d . . . . .
H20 H 0.3203 0.2151 0.6457 0.043 Uiso 1 1 calc R U . . .
C21 C 0.2606(3) 0.19771(15) 0.56988(10) 0.0461(7) Uani 1 1 d . . . . .
H21 H 0.2034 0.2368 0.5668 0.055 Uiso 1 1 calc R U . . .
C22 C 0.2764(3) 0.15304(17) 0.52778(11) 0.0540(8) Uani 1 1 d . . . . .
H22 H 0.2288 0.1622 0.4964 0.065 Uiso 1 1 calc R U . . .
C23 C 0.3598(3) 0.09545(16) 0.53043(10) 0.0495(7) Uani 1 1 d . . . . .
H23 H 0.3710 0.0657 0.5015 0.059 Uiso 1 1 calc R U . . .
C24 C 0.4263(3) 0.08342(13) 0.57732(9) 0.0376(6) Uani 1 1 d . . . . .
C25 C 0.2474(4) 0.16301(16) 0.35155(12) 0.0648(9) Uani 1 1 d . . . . .
H25A H 0.2222 0.1241 0.3287 0.078 Uiso 1 1 calc R U . . .
H25B H 0.2765 0.2017 0.3291 0.078 Uiso 1 1 calc R U . . .
Cl2 Cl 0.10413(10) 0.18848(5) 0.38831(3) 0.0698(3) Uani 1 1 d . . . . .
Cl3 Cl 0.38352(10) 0.13802(4) 0.39185(3) 0.0687(3) Uani 1 1 d . . . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4364(15) . ?
S1 O2 1.4424(16) . ?
S1 C16 1.775(2) . ?
S1 C2 1.782(2) . ?
Cl1 C7 1.731(2) . ?
O3 C9 1.369(3) . ?
O3 C1 1.374(3) . ?
O4 C1 1.199(2) . ?
O5 C24 1.371(3) . ?
O5 C17 1.445(3) . ?
C1 C2 1.471(3) . ?
C2 C3 1.360(3) . ?
C3 C4 1.449(3) . ?
C3 C10 1.495(3) . ?
C4 C9 1.395(3) . ?
C4 C5 1.405(3) . ?
C5 C6 1.374(3) . ?
C6 C7 1.384(4) . ?
C7 C8 1.377(3) . ?
C8 C9 1.388(3) . ?
C10 C15 1.389(3) . ?
C10 C11 1.389(3) . ?
C11 C12 1.383(3) . ?
C12 C13 1.388(3) . ?
C13 C14 1.385(3) . ?
C14 C15 1.383(3) . ?
C16 C18 1.519(3) . ?
C17 C18 1.553(3) . ?
C18 C19 1.513(3) . ?
C19 C20 1.379(3) . ?
C19 C24 1.383(3) . ?
C20 C21 1.397(3) . ?
C21 C22 1.382(4) . ?
C22 C23 1.378(4) . ?
C23 C24 1.378(3) . ?
C25 Cl3 1.747(4) . ?
C25 Cl2 1.754(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 117.16(10) . . ?
O1 S1 C16 109.32(10) . . ?
O2 S1 C16 107.15(10) . . ?
O1 S1 C2 108.81(9) . . ?
O2 S1 C2 107.41(9) . . ?
C16 S1 C2 106.47(10) . . ?
C9 O3 C1 122.39(16) . . ?
C24 O5 C17 107.47(17) . . ?
O4 C1 O3 116.96(18) . . ?
O4 C1 C2 126.2(2) . . ?
O3 C1 C2 116.82(17) . . ?
C3 C2 C1 121.97(19) . . ?
C3 C2 S1 124.54(16) . . ?
C1 C2 S1 113.29(14) . . ?
C2 C3 C4 118.40(18) . . ?
C2 C3 C10 125.30(19) . . ?
C4 C3 C10 116.30(17) . . ?
C9 C4 C5 117.1(2) . . ?
C9 C4 C3 119.16(19) . . ?
C5 C4 C3 123.78(19) . . ?
C6 C5 C4 121.1(2) . . ?
C5 C6 C7 119.5(2) . . ?
C8 C7 C6 121.9(2) . . ?
C8 C7 Cl1 119.2(2) . . ?
C6 C7 Cl1 118.82(19) . . ?
C7 C8 C9 117.5(2) . . ?
O3 C9 C8 115.97(19) . . ?
O3 C9 C4 121.15(19) . . ?
C8 C9 C4 122.9(2) . . ?
C15 C10 C11 119.83(19) . . ?
C15 C10 C3 120.29(19) . . ?
C11 C10 C3 119.75(18) . . ?
C12 C11 C10 119.8(2) . . ?
C11 C12 C13 120.2(2) . . ?
C14 C13 C12 120.0(2) . . ?
C15 C14 C13 119.9(2) . . ?
C14 C15 C10 120.3(2) . . ?
C18 C16 S1 114.95(15) . . ?
O5 C17 C18 107.56(18) . . ?
C19 C18 C16 111.38(18) . . ?
C19 C18 C17 101.12(17) . . ?
C16 C18 C17 114.51(19) . . ?
C20 C19 C24 119.9(2) . . ?
C20 C19 C18 131.5(2) . . ?
C24 C19 C18 108.5(2) . . ?
C19 C20 C21 118.6(2) . . ?
C22 C21 C20 120.0(3) . . ?
C23 C22 C21 121.9(2) . . ?
C24 C23 C22 117.2(3) . . ?
O5 C24 C23 124.0(2) . . ?
O5 C24 C19 113.6(2) . . ?
C23 C24 C19 122.4(2) . . ?
Cl3 C25 Cl2 111.85(17) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 O3 C1 O4 -177.6(2) . . . . ?
C9 O3 C1 C2 3.3(3) . . . . ?
O4 C1 C2 C3 -179.6(2) . . . . ?
O3 C1 C2 C3 -0.6(3) . . . . ?
O4 C1 C2 S1 5.4(3) . . . . ?
O3 C1 C2 S1 -175.60(15) . . . . ?
O1 S1 C2 C3 1.8(2) . . . . ?
O2 S1 C2 C3 -125.96(18) . . . . ?
C16 S1 C2 C3 119.52(19) . . . . ?
O1 S1 C2 C1 176.69(14) . . . . ?
O2 S1 C2 C1 48.93(17) . . . . ?
C16 S1 C2 C1 -65.59(17) . . . . ?
C1 C2 C3 C4 -1.5(3) . . . . ?
S1 C2 C3 C4 173.00(15) . . . . ?
C1 C2 C3 C10 178.06(19) . . . . ?
S1 C2 C3 C10 -7.5(3) . . . . ?
C2 C3 C4 C9 0.9(3) . . . . ?
C10 C3 C4 C9 -178.66(19) . . . . ?
C2 C3 C4 C5 -178.9(2) . . . . ?
C10 C3 C4 C5 1.5(3) . . . . ?
C9 C4 C5 C6 -0.4(4) . . . . ?
C3 C4 C5 C6 179.4(2) . . . . ?
C4 C5 C6 C7 -0.1(4) . . . . ?
C5 C6 C7 C8 0.6(4) . . . . ?
C5 C6 C7 Cl1 -179.5(2) . . . . ?
C6 C7 C8 C9 -0.7(4) . . . . ?
Cl1 C7 C8 C9 179.5(2) . . . . ?
C1 O3 C9 C8 177.2(2) . . . . ?
C1 O3 C9 C4 -4.0(3) . . . . ?
C7 C8 C9 O3 179.0(2) . . . . ?
C7 C8 C9 C4 0.2(4) . . . . ?
C5 C4 C9 O3 -178.5(2) . . . . ?
C3 C4 C9 O3 1.7(3) . . . . ?
C5 C4 C9 C8 0.3(3) . . . . ?
C3 C4 C9 C8 -179.5(2) . . . . ?
C2 C3 C10 C15 101.8(3) . . . . ?
C4 C3 C10 C15 -78.6(3) . . . . ?
C2 C3 C10 C11 -82.2(3) . . . . ?
C4 C3 C10 C11 97.3(2) . . . . ?
C15 C10 C11 C12 -1.5(3) . . . . ?
C3 C10 C11 C12 -177.4(2) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
C11 C12 C13 C14 1.1(4) . . . . ?
C12 C13 C14 C15 -0.5(4) . . . . ?
C13 C14 C15 C10 -1.1(3) . . . . ?
C11 C10 C15 C14 2.1(3) . . . . ?
C3 C10 C15 C14 178.0(2) . . . . ?
O1 S1 C16 C18 38.62(19) . . . . ?
O2 S1 C16 C18 166.54(16) . . . . ?
C2 S1 C16 C18 -78.77(17) . . . . ?
C24 O5 C17 C18 13.0(3) . . . . ?
S1 C16 C18 C19 -179.91(16) . . . . ?
S1 C16 C18 C17 -65.9(2) . . . . ?
O5 C17 C18 C19 -12.4(2) . . . . ?
O5 C17 C18 C16 -132.3(2) . . . . ?
C16 C18 C19 C20 -50.2(3) . . . . ?
C17 C18 C19 C20 -172.3(2) . . . . ?
C16 C18 C19 C24 129.7(2) . . . . ?
C17 C18 C19 C24 7.7(2) . . . . ?
C24 C19 C20 C21 1.1(4) . . . . ?
C18 C19 C20 C21 -178.9(2) . . . . ?
C19 C20 C21 C22 -0.6(4) . . . . ?
C20 C21 C22 C23 -0.4(5) . . . . ?
C21 C22 C23 C24 0.8(5) . . . . ?
C17 O5 C24 C23 172.3(3) . . . . ?
C17 O5 C24 C19 -8.4(3) . . . . ?
C22 C23 C24 O5 179.0(3) . . . . ?
C22 C23 C24 C19 -0.3(4) . . . . ?
C20 C19 C24 O5 179.9(2) . . . . ?
C18 C19 C24 O5 -0.1(3) . . . . ?
C20 C19 C24 C23 -0.7(4) . . . . ?
C18 C19 C24 C23 179.3(2) . . . . ?

_refine_diff_density_max         0.273
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.055



