# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1492583'
_audit_update_record             
;
2016-07-12 deposited with the CCDC.
2016-10-11 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            'C31 H23 Cl3 N2 O3 S'
_chemical_formula_weight         609.92

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'
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           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   8.0194(5)
_cell_length_b                   16.8849(11)
_cell_length_c                   20.7855(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2814.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9820
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      26.02

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_F_000             1256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.437
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(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            117951
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.109
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4957
_reflns_number_gt                4563
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0165P)²+2.2997P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.02(7)
_chemical_absolute_configuration Syn
_refine_ls_number_reflns         4957
_refine_ls_number_parameters     454
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_ref         0.0705
_refine_ls_wR_factor_gt          0.0683
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.000
_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
C35 C 0.4451(5) 0.3175(3) 0.01804(19) 0.0361(9) Uani 1 1 d . . . . .
Cl3 Cl 0.4242(2) 0.21999(8) 0.04407(8) 0.0930(6) Uani 1 1 d . . . . .
O4 O 0.3426(3) -0.09682(15) -0.23158(11) 0.0316(6) Uani 1 1 d . . . . .
H13 H 0.325(5) -0.416(2) -0.0400(17) 0.028(10) Uiso 1 1 d . . . . .
H7 H 0.378(4) 0.251(2) -0.2028(16) 0.019(9) Uiso 1 1 d . . . . .
H12 H 0.186(5) -0.268(2) -0.2166(17) 0.029(10) Uiso 1 1 d . . . . .
H20 H 0.062(4) -0.0428(19) -0.1762(16) 0.015(8) Uiso 1 1 d . . . . .
H19 H -0.013(4) -0.005(2) -0.1123(16) 0.020(8) Uiso 1 1 d . . . . .
H9 H -0.038(5) 0.118(2) -0.2081(16) 0.023(9) Uiso 1 1 d . . . . .
H17 H -0.370(5) -0.209(2) -0.1541(17) 0.028(10) Uiso 1 1 d . . . . .
H18 H -0.143(4) -0.135(2) -0.1245(16) 0.019(9) Uiso 1 1 d . . . . .
H6 H 0.523(5) 0.149(2) -0.1495(18) 0.032(10) Uiso 1 1 d . . . . .
H21 H 0.108(5) -0.158(2) 0.015(2) 0.040(12) Uiso 1 1 d . . . . .
H8 H 0.100(4) 0.236(2) -0.2356(17) 0.025(9) Uiso 1 1 d . . . . .
H15 H -0.108(4) -0.408(2) -0.1114(16) 0.025(10) Uiso 1 1 d . . . . .
H3 H 0.234(6) -0.593(3) -0.260(2) 0.059(14) Uiso 1 1 d . . . . .
H16 H -0.354(5) -0.343(2) -0.1486(18) 0.034(11) Uiso 1 1 d . . . . .
H10 H 0.377(5) -0.087(2) -0.324(2) 0.043(12) Uiso 1 1 d . . . . .
H11 H 0.250(6) -0.226(3) -0.331(2) 0.053(13) Uiso 1 1 d . . . . .
H5 H 0.074(6) -0.547(3) -0.090(2) 0.053(15) Uiso 1 1 d . . . . .
H1 H 0.369(5) -0.392(2) -0.1721(18) 0.033(10) Uiso 1 1 d . . . . .
H14 H 0.134(5) -0.434(3) -0.029(2) 0.050(13) Uiso 1 1 d . . . . .
H4 H 0.077(6) -0.631(3) -0.176(2) 0.056(13) Uiso 1 1 d . . . . .
H2 H 0.383(6) -0.471(3) -0.262(2) 0.060(15) Uiso 1 1 d . . . . .
H30 H 0.553(5) 0.337(2) 0.0300(18) 0.036(11) Uiso 1 1 d . . . . .
H31 H 0.388(4) -0.1457(18) -0.1065(15) 0.010(8) Uiso 1 1 d . . . . .
C1 C 0.2775(4) -0.15596(19) -0.19392(15) 0.0197(7) Uani 1 1 d . . . . .
C2 C 0.2339(5) -0.2178(2) -0.23008(17) 0.0263(8) Uani 1 1 d . . . . .
C3 C 0.2718(5) -0.1970(2) -0.29503(17) 0.0308(9) Uani 1 1 d . . . . .
C5 C 0.2817(4) -0.13771(18) -0.12347(15) 0.0172(7) Uani 1 1 d . . . . .
C6 C 0.1741(4) -0.19129(18) -0.07954(14) 0.0184(7) Uani 1 1 d . . . . .
C7 C 0.2347(4) -0.05252(18) -0.10398(15) 0.0190(7) Uani 1 1 d . . . . .
C8 C 0.1889(4) -0.06299(19) -0.03346(15) 0.0216(7) Uani 1 1 d . . . . .
C9 C 0.4089(5) 0.1447(2) -0.16147(18) 0.0287(8) Uani 1 1 d . . . . .
C10 C 0.3257(5) 0.2037(2) -0.19388(17) 0.0305(9) Uani 1 1 d . . . . .
C11 C 0.1586(5) 0.1944(2) -0.21022(17) 0.0291(8) Uani 1 1 d . . . . .
C12 C 0.0725(5) 0.1262(2) -0.19433(16) 0.0253(8) Uani 1 1 d . . . . .
C13 C 0.1563(4) 0.06673(18) -0.16174(15) 0.0201(7) Uani 1 1 d . . . . .
C14 C 0.3217(4) 0.07605(19) -0.14538(15) 0.0213(7) Uani 1 1 d . . . . .
C15 C 0.0879(4) -0.0129(2) -0.14077(17) 0.0204(7) Uani 1 1 d . . . . .
C16 C 0.3841(4) 0.0048(2) -0.11246(16) 0.0227(7) Uani 1 1 d . . . . .
C19 C 0.2706(4) -0.26795(19) -0.06226(14) 0.0186(7) Uani 1 1 d . . . . .
C20 C 0.0079(4) -0.22306(19) -0.10245(14) 0.0182(7) Uani 1 1 d . . . . .
C21 C 0.0131(4) -0.30549(19) -0.09817(15) 0.0205(7) Uani 1 1 d . . . . .
C22 C -0.1214(4) -0.3523(2) -0.11426(17) 0.0261(8) Uani 1 1 d . . . . .
C23 C -0.2645(5) -0.3141(2) -0.13506(17) 0.0306(9) Uani 1 1 d . . . . .
C24 C -0.2728(5) -0.2325(2) -0.13851(17) 0.0285(8) Uani 1 1 d . . . . .
C25 C -0.1361(4) -0.1864(2) -0.12125(16) 0.0228(7) Uani 1 1 d . . . . .
C26 C 0.2110(6) -0.4131(2) -0.05985(17) 0.0292(8) Uani 1 1 d . . . . .
C27 C 0.2153(4) -0.46400(19) -0.11931(17) 0.0258(8) Uani 1 1 d . . . . .
C28 C 0.3077(5) -0.4412(2) -0.17256(19) 0.0331(9) Uani 1 1 d . . . . .
C29 C 0.3154(6) -0.4890(3) -0.2265(2) 0.0481(12) Uani 1 1 d . . . . .
C30 C 0.2310(6) -0.5599(3) -0.2269(2) 0.0527(14) Uani 1 1 d . . . . .
C31 C 0.1371(6) -0.5824(3) -0.1749(3) 0.0543(14) Uani 1 1 d . . . . .
C32 C 0.1308(6) -0.5348(2) -0.1213(3) 0.0440(11) Uani 1 1 d . . . . .
N1 N 0.1588(3) -0.13944(15) -0.02353(13) 0.0194(6) Uani 1 1 d . . . . .
N2 N 0.1688(4) -0.33053(15) -0.07383(13) 0.0222(6) Uani 1 1 d . . . . .
C4 C 0.3353(5) -0.1245(3) -0.29380(17) 0.0340(9) Uani 1 1 d . . . . .
O2 O 0.5252(3) -0.01049(15) -0.09608(13) 0.0337(6) Uani 1 1 d . . . . .
O3 O 0.4139(3) -0.26998(13) -0.04317(11) 0.0237(5) Uani 1 1 d . . . . .
S1 S 0.17061(13) 0.00843(5) 0.02050(4) 0.0319(2) Uani 1 1 d . . . . .
Cl1 Cl 0.43710(17) 0.32090(8) -0.06587(5) 0.0556(3) Uani 1 1 d . . . . .
Cl2 Cl 0.28782(12) 0.37740(6) 0.05177(5) 0.0413(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
C35 Cl3 1.742(4) . ?
C35 Cl1 1.746(4) . ?
C35 Cl2 1.762(4) . ?
O4 C1 1.372(4) . ?
O4 C4 1.376(4) . ?
C1 C2 1.334(5) . ?
C1 C5 1.497(4) . ?
C2 C3 1.428(5) . ?
C3 C4 1.327(6) . ?
C5 C7 1.541(4) . ?
C5 C6 1.548(4) . ?
C6 N1 1.462(4) . ?
C6 C20 1.514(4) . ?
C6 C19 1.550(4) . ?
C7 C8 1.522(4) . ?
C7 C16 1.550(4) . ?
C7 C15 1.555(4) . ?
C8 N1 1.329(4) . ?
C8 S1 1.653(3) . ?
C9 C10 1.376(5) . ?
C9 C14 1.394(5) . ?
C10 C11 1.392(6) . ?
C11 C12 1.382(5) . ?
C12 C13 1.385(5) . ?
C13 C14 1.379(5) . ?
C13 C15 1.516(5) . ?
C14 C16 1.472(5) . ?
C16 O2 1.210(4) . ?
C19 O3 1.216(4) . ?
C19 N2 1.357(4) . ?
C20 C25 1.367(5) . ?
C20 C21 1.395(5) . ?
C21 C22 1.378(5) . ?
C21 N2 1.412(4) . ?
C22 C23 1.386(5) . ?
C23 C24 1.382(6) . ?
C24 C25 1.392(5) . ?
C26 N2 1.464(4) . ?
C26 C27 1.505(5) . ?
C27 C32 1.374(5) . ?
C27 C28 1.386(5) . ?
C28 C29 1.383(6) . ?
C29 C30 1.375(7) . ?
C30 C31 1.371(8) . ?
C31 C32 1.374(6) . ?

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
Cl3 C35 Cl1 109.7(2) . . ?
Cl3 C35 Cl2 110.5(2) . . ?
Cl1 C35 Cl2 110.6(2) . . ?
C1 O4 C4 105.8(3) . . ?
C2 C1 O4 110.4(3) . . ?
C2 C1 C5 135.9(3) . . ?
O4 C1 C5 113.6(3) . . ?
C1 C2 C3 106.5(3) . . ?
C4 C3 C2 106.9(3) . . ?
C1 C5 C7 116.3(3) . . ?
C1 C5 C6 116.4(3) . . ?
C7 C5 C6 104.7(2) . . ?
N1 C6 C20 112.9(3) . . ?
N1 C6 C5 99.6(2) . . ?
C20 C6 C5 120.8(3) . . ?
N1 C6 C19 111.0(2) . . ?
C20 C6 C19 102.5(2) . . ?
C5 C6 C19 110.3(3) . . ?
C8 C7 C5 101.8(2) . . ?
C8 C7 C16 111.6(3) . . ?
C5 C7 C16 111.3(3) . . ?
C8 C7 C15 109.9(3) . . ?
C5 C7 C15 117.2(3) . . ?
C16 C7 C15 105.1(3) . . ?
N1 C8 C7 107.8(3) . . ?
N1 C8 S1 125.9(3) . . ?
C7 C8 S1 126.2(2) . . ?
C10 C9 C14 118.5(3) . . ?
C9 C10 C11 120.3(3) . . ?
C12 C11 C10 121.1(4) . . ?
C11 C12 C13 118.6(3) . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 C15 112.2(3) . . ?
C12 C13 C15 127.5(3) . . ?
C13 C14 C9 121.2(3) . . ?
C13 C14 C16 110.4(3) . . ?
C9 C14 C16 128.4(3) . . ?
C13 C15 C7 104.4(3) . . ?
O2 C16 C14 128.6(3) . . ?
O2 C16 C7 123.9(3) . . ?
C14 C16 C7 107.5(3) . . ?
O3 C19 N2 127.2(3) . . ?
O3 C19 C6 124.8(3) . . ?
N2 C19 C6 108.0(3) . . ?
C25 C20 C21 119.6(3) . . ?
C25 C20 C6 132.3(3) . . ?
C21 C20 C6 107.9(3) . . ?
C22 C21 C20 122.2(3) . . ?
C22 C21 N2 127.4(3) . . ?
C20 C21 N2 110.4(3) . . ?
C21 C22 C23 117.2(3) . . ?
C24 C23 C22 121.4(4) . . ?
C23 C24 C25 120.4(4) . . ?
C20 C25 C24 119.1(3) . . ?
N2 C26 C27 112.7(3) . . ?
C32 C27 C28 118.7(4) . . ?
C32 C27 C26 120.6(4) . . ?
C28 C27 C26 120.6(3) . . ?
C29 C28 C27 120.6(4) . . ?
C30 C29 C28 119.4(4) . . ?
C31 C30 C29 120.4(4) . . ?
C30 C31 C32 119.8(5) . . ?
C31 C32 C27 121.0(5) . . ?
C8 N1 C6 116.3(3) . . ?
C19 N2 C21 111.2(3) . . ?
C19 N2 C26 124.6(3) . . ?
C21 N2 C26 124.1(3) . . ?
C3 C4 O4 110.3(3) . . ?

_refine_diff_density_max         0.581
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.042

