# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 1549207'
_audit_update_record             
;
2017-05-11 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            'C20 H15 Cl O4 S'
_chemical_formula_weight         386.83

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   26.3420(19)
_cell_length_b                   8.9941(7)
_cell_length_c                   20.0725(13)
_cell_angle_alpha                90
_cell_angle_beta                 130.740(7)
_cell_angle_gamma                90
_cell_volume                     3603.2(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3989
_cell_measurement_theta_min      4.43
_cell_measurement_theta_max      66.42

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_F_000             1600
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    3.160
_shelx_estimated_absorpt_T_min   0.543
_shelx_estimated_absorpt_T_max   0.600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9837
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.430
_diffrn_reflns_theta_max         66.767
_diffrn_reflns_theta_full        66.767
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             3123
_reflns_number_gt                2512
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0678P)²+2.8604P] 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         3123
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1212
_refine_ls_wR_factor_gt          0.1124
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.001
_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
C1 C 0.83133(12) 0.8605(3) 0.65562(16) 0.0438(6) Uani 1 1 d . . . . .
H1 H 0.8688 0.8202 0.7085 0.053 Uiso 1 1 calc R U . . .
C2 C 0.83797(14) 0.9637(3) 0.61003(18) 0.0498(7) Uani 1 1 d . . . . .
C3 C 0.78379(14) 1.0226(3) 0.53111(18) 0.0528(7) Uani 1 1 d . . . . .
H3 H 0.7901 1.0929 0.5031 0.063 Uiso 1 1 calc R U . . .
C4 C 0.71984(14) 0.9775(3) 0.49313(17) 0.0471(6) Uani 1 1 d . . . . .
H4 H 0.6827 1.0130 0.4383 0.057 Uiso 1 1 calc R U . . .
C5 C 0.71254(11) 0.8786(3) 0.53881(14) 0.0371(5) Uani 1 1 d . . . . .
C6 C 0.76769(12) 0.8200(3) 0.61990(14) 0.0360(5) Uani 1 1 d . . . . .
C7 C 0.74629(12) 0.7292(2) 0.65817(15) 0.0354(5) Uani 1 1 d . . . . .
C8 C 0.67940(12) 0.7231(2) 0.61044(14) 0.0338(5) Uani 1 1 d . . . . .
C9 C 0.63738(11) 0.6749(2) 0.63271(14) 0.0330(5) Uani 1 1 d . . . . .
H9 H 0.5987 0.7421 0.6004 0.040 Uiso 1 1 calc R U . . .
C10 C 0.67589(12) 0.7042(2) 0.73049(14) 0.0352(5) Uani 1 1 d . . . . .
C11 C 0.73776(12) 0.6558(3) 0.79311(15) 0.0407(6) Uani 1 1 d . . . . .
H11 H 0.7581 0.6744 0.8514 0.049 Uiso 1 1 calc R U . . .
C12 C 0.77633(13) 0.5728(3) 0.77441(16) 0.0439(6) Uani 1 1 d . . . . .
H12A H 0.8159 0.5293 0.8285 0.053 Uiso 1 1 calc R U . . .
H12B H 0.7490 0.4927 0.7336 0.053 Uiso 1 1 calc R U . . .
C13 C 0.64479(14) 0.7964(3) 0.75700(17) 0.0459(6) Uani 1 1 d . . . . .
C14 C 0.5505(2) 0.9353(5) 0.7088(3) 0.0963(14) Uani 1 1 d . . . . .
H14A H 0.5472 0.8847 0.7479 0.144 Uiso 1 1 calc R U . . .
H14B H 0.5065 0.9595 0.6552 0.144 Uiso 1 1 calc R U . . .
H14C H 0.5760 1.0250 0.7361 0.144 Uiso 1 1 calc R U . . .
C15 C 0.60847(11) 0.5178(2) 0.60524(14) 0.0351(5) Uani 1 1 d . . . . .
C16 C 0.56558(12) 0.4705(3) 0.61888(16) 0.0449(6) Uani 1 1 d . . . . .
H16 H 0.5559 0.5336 0.6461 0.054 Uiso 1 1 calc R U . . .
C17 C 0.53733(14) 0.3309(3) 0.59229(18) 0.0544(7) Uani 1 1 d . . . . .
H17 H 0.5091 0.3001 0.6023 0.065 Uiso 1 1 calc R U . . .
C18 C 0.55033(14) 0.2370(3) 0.55129(19) 0.0591(8) Uani 1 1 d . . . . .
H18 H 0.5310 0.1429 0.5337 0.071 Uiso 1 1 calc R U . . .
C19 C 0.59168(15) 0.2818(3) 0.5363(2) 0.0579(7) Uani 1 1 d . . . . .
H19 H 0.6003 0.2186 0.5080 0.070 Uiso 1 1 calc R U . . .
C20 C 0.62094(13) 0.4220(3) 0.56343(17) 0.0463(6) Uani 1 1 d . . . . .
H20 H 0.6492 0.4518 0.5533 0.056 Uiso 1 1 calc R U . . .
Cl1 Cl 0.91784(4) 1.02268(12) 0.65691(6) 0.0794(3) Uani 1 1 d . . . . .
O1 O 0.59403(9) 0.9316(2) 0.49539(13) 0.0540(5) Uani 1 1 d . . . . .
O2 O 0.79625(8) 0.6699(2) 0.73731(10) 0.0446(4) Uani 1 1 d . . . . .
O3 O 0.67248(12) 0.8303(3) 0.83144(13) 0.0770(7) Uani 1 1 d . . . . .
O4 O 0.58344(10) 0.8405(3) 0.68936(13) 0.0641(6) Uani 1 1 d . . . . .
S1 S 0.63583(3) 0.80841(7) 0.50554(3) 0.03743(19) 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
C1 C6 1.374(3) . ?
C1 C2 1.392(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.370(4) . ?
C2 Cl1 1.735(3) . ?
C3 C4 1.381(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.397(3) . ?
C5 S1 1.779(2) . ?
C6 C7 1.463(3) . ?
C7 O2 1.346(3) . ?
C7 C8 1.350(3) . ?
C8 C9 1.503(3) . ?
C8 S1 1.785(2) . ?
C9 C15 1.527(3) . ?
C9 C10 1.534(3) . ?
C9 H9 0.9800 . ?
C10 C11 1.323(3) . ?
C10 C13 1.487(3) . ?
C11 C12 1.493(4) . ?
C11 H11 0.9300 . ?
C12 O2 1.450(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O3 1.198(3) . ?
C13 O4 1.322(3) . ?
C14 O4 1.439(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C20 1.383(3) . ?
C15 C16 1.391(3) . ?
C16 C17 1.377(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.370(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.366(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.390(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
O1 S1 1.4795(19) . ?

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
C6 C1 C2 117.9(2) . . ?
C6 C1 H1 121.1 . . ?
C2 C1 H1 121.1 . . ?
C3 C2 C1 122.3(2) . . ?
C3 C2 Cl1 119.2(2) . . ?
C1 C2 Cl1 118.4(2) . . ?
C2 C3 C4 120.0(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 118.1(2) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C4 C5 C6 121.9(2) . . ?
C4 C5 S1 126.63(19) . . ?
C6 C5 S1 111.49(17) . . ?
C1 C6 C5 119.7(2) . . ?
C1 C6 C7 129.1(2) . . ?
C5 C6 C7 111.0(2) . . ?
O2 C7 C8 129.8(2) . . ?
O2 C7 C6 115.2(2) . . ?
C8 C7 C6 115.0(2) . . ?
C7 C8 C9 132.4(2) . . ?
C7 C8 S1 110.86(16) . . ?
C9 C8 S1 116.33(16) . . ?
C8 C9 C15 116.74(18) . . ?
C8 C9 C10 109.30(18) . . ?
C15 C9 C10 112.26(17) . . ?
C8 C9 H9 105.9 . . ?
C15 C9 H9 105.9 . . ?
C10 C9 H9 105.9 . . ?
C11 C10 C13 117.9(2) . . ?
C11 C10 C9 122.3(2) . . ?
C13 C10 C9 119.7(2) . . ?
C10 C11 C12 123.0(2) . . ?
C10 C11 H11 118.5 . . ?
C12 C11 H11 118.5 . . ?
O2 C12 C11 111.22(19) . . ?
O2 C12 H12A 109.4 . . ?
C11 C12 H12A 109.4 . . ?
O2 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
O3 C13 O4 123.1(3) . . ?
O3 C13 C10 124.0(3) . . ?
O4 C13 C10 112.9(2) . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 118.3(2) . . ?
C20 C15 C9 122.3(2) . . ?
C16 C15 C9 119.3(2) . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C16 120.8(3) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C19 C18 C17 119.9(3) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 120.0(3) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C15 C20 C19 120.7(3) . . ?
C15 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C7 O2 C12 116.22(18) . . ?
C13 O4 C14 116.6(2) . . ?
O1 S1 C5 110.30(11) . . ?
O1 S1 C8 109.42(11) . . ?
C5 S1 C8 90.65(11) . . ?

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
C6 C1 C2 C3 -1.4(4) . . . . ?
C6 C1 C2 Cl1 176.89(19) . . . . ?
C1 C2 C3 C4 -1.4(4) . . . . ?
Cl1 C2 C3 C4 -179.6(2) . . . . ?
C2 C3 C4 C5 3.1(4) . . . . ?
C3 C4 C5 C6 -2.2(4) . . . . ?
C3 C4 C5 S1 178.1(2) . . . . ?
C2 C1 C6 C5 2.2(3) . . . . ?
C2 C1 C6 C7 -172.0(2) . . . . ?
C4 C5 C6 C1 -0.5(4) . . . . ?
S1 C5 C6 C1 179.24(18) . . . . ?
C4 C5 C6 C7 174.7(2) . . . . ?
S1 C5 C6 C7 -5.6(2) . . . . ?
C1 C6 C7 O2 -4.4(3) . . . . ?
C5 C6 C7 O2 -178.97(19) . . . . ?
C1 C6 C7 C8 172.8(2) . . . . ?
C5 C6 C7 C8 -1.8(3) . . . . ?
O2 C7 C8 C9 12.6(4) . . . . ?
C6 C7 C8 C9 -164.0(2) . . . . ?
O2 C7 C8 S1 -175.1(2) . . . . ?
C6 C7 C8 S1 8.2(2) . . . . ?
C7 C8 C9 C15 -99.0(3) . . . . ?
S1 C8 C9 C15 89.1(2) . . . . ?
C7 C8 C9 C10 29.8(3) . . . . ?
S1 C8 C9 C10 -142.16(16) . . . . ?
C8 C9 C10 C11 -52.2(3) . . . . ?
C15 C9 C10 C11 79.0(3) . . . . ?
C8 C9 C10 C13 124.7(2) . . . . ?
C15 C9 C10 C13 -104.1(2) . . . . ?
C13 C10 C11 C12 -175.0(2) . . . . ?
C9 C10 C11 C12 2.0(4) . . . . ?
C10 C11 C12 O2 71.5(3) . . . . ?
C11 C10 C13 O3 0.5(4) . . . . ?
C9 C10 C13 O3 -176.5(3) . . . . ?
C11 C10 C13 O4 179.1(2) . . . . ?
C9 C10 C13 O4 2.1(3) . . . . ?
C8 C9 C15 C20 1.3(3) . . . . ?
C10 C9 C15 C20 -126.1(2) . . . . ?
C8 C9 C15 C16 -175.8(2) . . . . ?
C10 C9 C15 C16 56.9(3) . . . . ?
C20 C15 C16 C17 0.9(4) . . . . ?
C9 C15 C16 C17 178.1(2) . . . . ?
C15 C16 C17 C18 -0.7(4) . . . . ?
C16 C17 C18 C19 -0.1(4) . . . . ?
C17 C18 C19 C20 0.6(4) . . . . ?
C16 C15 C20 C19 -0.4(4) . . . . ?
C9 C15 C20 C19 -177.5(2) . . . . ?
C18 C19 C20 C15 -0.3(4) . . . . ?
C8 C7 O2 C12 6.6(3) . . . . ?
C6 C7 O2 C12 -176.74(19) . . . . ?
C11 C12 O2 C7 -64.3(3) . . . . ?
O3 C13 O4 C14 1.0(5) . . . . ?
C10 C13 O4 C14 -177.6(3) . . . . ?
C4 C5 S1 O1 -60.7(2) . . . . ?
C6 C5 S1 O1 119.55(18) . . . . ?
C4 C5 S1 C8 -171.8(2) . . . . ?
C6 C5 S1 C8 8.53(18) . . . . ?
C7 C8 S1 O1 -121.32(17) . . . . ?
C9 C8 S1 O1 52.31(19) . . . . ?
C7 C8 S1 C5 -9.49(18) . . . . ?
C9 C8 S1 C5 164.14(17) . . . . ?

_refine_diff_density_max         0.376
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_9
_database_code_depnum_ccdc_archive 'CCDC 1545864'
_audit_update_record             
;
2017-04-25 deposited with the CCDC.
2017-09-05 downloaded from the CCDC.
;
_audit_creation_date             2017-04-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H12 O S'
_chemical_formula_sum            'C16 H12 O S'
_chemical_formula_weight         252.32
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.111(2)
_cell_length_b                   7.5844(17)
_cell_length_c                   10.765(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.27(3)
_cell_angle_gamma                90
_cell_volume                     641.7(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    809
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.0890
_cell_measurement_theta_min      2.7480
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.7e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2820
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        24.984
_diffrn_reflns_theta_max         24.984
_diffrn_reflns_theta_min         1.952
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -75.00 120.00   1.00    8.00    --   30.00  54.00 120.00  195
  2  ω    -75.00  30.00   1.00    8.00    --   30.00  54.00 240.00  105
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0284543000
_diffrn_orient_matrix_UB_12      -0.0322360000
_diffrn_orient_matrix_UB_13      0.0528645000
_diffrn_orient_matrix_UB_21      -0.0806083000
_diffrn_orient_matrix_UB_22      -0.0199679000
_diffrn_orient_matrix_UB_23      -0.0413225000
_diffrn_orient_matrix_UB_31      0.0298772000
_diffrn_orient_matrix_UB_32      -0.0854119000
_diffrn_orient_matrix_UB_33      -0.0100235000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.789
_reflns_Friedel_fraction_full    0.931
_reflns_Friedel_fraction_max     0.931
_reflns_number_gt                1744
_reflns_number_total             2186
_reflns_odcompleteness_completeness 88.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.91
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 565 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.18(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2186
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0563
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1416
_refine_ls_wR_factor_ref         0.1780
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C005(H005), C009(H009), C00A(H00A), C00B(H00B), C00D(H00D), C00E(H00E),
 C00F(H00F), C00G(H00G), C00H(H00H)
2.b Idealised Me refined as rotating group:
 C00I(H00C,H00I,H00J)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
S001 S 0.4911(2) 0.6062(3) 0.60423(15) 0.0609(6) Uani 1 1 d . . . . .
O002 O 0.8267(6) 0.3823(7) 0.8815(5) 0.0707(14) Uani 1 1 d . . . . .
C003 C 0.5379(8) 0.4854(8) 0.8443(6) 0.0492(14) Uani 1 1 d . . . . .
C004 C 0.4186(7) 0.5707(8) 0.7454(5) 0.0496(16) Uani 1 1 d . . . . .
C005 C 0.4948(8) 0.4457(8) 0.9590(6) 0.0513(15) Uani 1 1 d . . . . .
H005 H 0.5741 0.3907 1.0249 0.062 Uiso 1 1 calc R . . . .
C006 C 0.8412(8) 0.5022(8) 0.4905(6) 0.0512(15) Uani 1 1 d . . . . .
C007 C 0.6983(8) 0.4480(9) 0.8099(6) 0.0525(15) Uani 1 1 d . . . . .
C008 C 0.3353(8) 0.4871(9) 0.9759(6) 0.0523(15) Uani 1 1 d . . . . .
C009 C 0.8163(8) 0.4665(8) 0.6192(6) 0.0518(15) Uani 1 1 d . . . . .
H009 H 0.9072 0.4083 0.6733 0.062 Uiso 1 1 calc R . . . .
C00A C 0.2609(8) 0.6199(12) 0.7615(6) 0.0556(15) Uani 1 1 d . . . . .
H00A H 0.1836 0.6799 0.6972 0.067 Uiso 1 1 calc R . . . .
C00B C 0.2208(8) 0.5768(9) 0.8769(6) 0.0557(16) Uani 1 1 d . . . . .
H00B H 0.1149 0.6086 0.8885 0.067 Uiso 1 1 calc R . . . .
C00C C 0.6885(8) 0.5017(9) 0.6731(6) 0.0525(15) Uani 1 1 d . . . . .
C00D C 0.7171(8) 0.5789(9) 0.3895(6) 0.0563(17) Uani 1 1 d . . . . .
H00D H 0.6112 0.6089 0.4021 0.068 Uiso 1 1 calc R . . . .
C00E C 0.7526(9) 0.6101(13) 0.2701(6) 0.0637(16) Uani 1 1 d . . . . .
H00E H 0.6694 0.6596 0.2041 0.076 Uiso 1 1 calc R . . . .
C00F C 0.9090(9) 0.5685(10) 0.2496(6) 0.066(2) Uani 1 1 d . . . . .
H00F H 0.9317 0.5907 0.1705 0.079 Uiso 1 1 calc R . . . .
C00G C 0.9981(8) 0.4591(8) 0.4660(6) 0.0552(16) Uani 1 1 d . . . . .
H00G H 1.0815 0.4065 0.5304 0.066 Uiso 1 1 calc R . . . .
C00H C 1.0324(9) 0.4931(10) 0.3477(7) 0.0639(18) Uani 1 1 d . . . . .
H00H H 1.1384 0.4652 0.3345 0.077 Uiso 1 1 calc R . . . .
C00I C 0.2819(10) 0.4411(11) 1.0976(7) 0.075(2) Uani 1 1 d . . . . .
H00C H 0.3682 0.3698 1.1518 0.113 Uiso 1 1 calc GR . . . .
H00I H 0.1766 0.3770 1.0759 0.113 Uiso 1 1 calc GR . . . .
H00J H 0.2670 0.5475 1.1419 0.113 Uiso 1 1 calc GR . . . .


_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
S001 C004 1.780(6) . ?
S001 C00C 1.776(7) . ?
O002 C007 1.238(7) . ?
C003 C004 1.408(8) . ?
C003 C005 1.397(9) . ?
C003 C007 1.466(9) . ?
C004 C00A 1.384(9) . ?
C005 H005 0.9300 . ?
C005 C008 1.386(9) . ?
C006 C009 1.474(8) . ?
C006 C00D 1.412(8) . ?
C006 C00G 1.401(9) . ?
C007 C00C 1.510(9) . ?
C008 C00B 1.405(9) . ?
C008 C00I 1.518(9) . ?
C009 H009 0.9300 . ?
C009 C00C 1.334(8) . ?
C00A H00A 0.9300 . ?
C00A C00B 1.399(9) . ?
C00B H00B 0.9300 . ?
C00D H00D 0.9300 . ?
C00D C00E 1.404(9) . ?
C00E H00E 0.9300 . ?
C00E C00F 1.377(10) . ?
C00F H00F 0.9300 . ?
C00F C00H 1.386(10) . ?
C00G H00G 0.9300 . ?
C00G C00H 1.393(10) . ?
C00H H00H 0.9300 . ?
C00I H00C 0.9600 . ?
C00I H00I 0.9600 . ?
C00I H00J 0.9600 . ?

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
C00C S001 C004 91.7(3) . . ?
C004 C003 C007 112.6(5) . . ?
C005 C003 C004 119.6(6) . . ?
C005 C003 C007 127.8(6) . . ?
C003 C004 S001 113.9(4) . . ?
C00A C004 S001 125.2(5) . . ?
C00A C004 C003 120.9(6) . . ?
C003 C005 H005 119.6 . . ?
C008 C005 C003 120.8(6) . . ?
C008 C005 H005 119.6 . . ?
C00D C006 C009 124.3(6) . . ?
C00G C006 C009 118.4(6) . . ?
C00G C006 C00D 117.3(6) . . ?
O002 C007 C003 125.7(6) . . ?
O002 C007 C00C 123.4(6) . . ?
C003 C007 C00C 111.0(5) . . ?
C005 C008 C00B 118.3(5) . . ?
C005 C008 C00I 122.4(6) . . ?
C00B C008 C00I 119.3(6) . . ?
C006 C009 H009 113.8 . . ?
C00C C009 C006 132.3(6) . . ?
C00C C009 H009 113.8 . . ?
C004 C00A H00A 120.9 . . ?
C004 C00A C00B 118.2(6) . . ?
C00B C00A H00A 120.9 . . ?
C008 C00B H00B 118.9 . . ?
C00A C00B C008 122.2(6) . . ?
C00A C00B H00B 118.9 . . ?
C007 C00C S001 110.7(4) . . ?
C009 C00C S001 128.7(5) . . ?
C009 C00C C007 120.7(6) . . ?
C006 C00D H00D 119.8 . . ?
C00E C00D C006 120.4(6) . . ?
C00E C00D H00D 119.8 . . ?
C00D C00E H00E 119.6 . . ?
C00F C00E C00D 120.8(7) . . ?
C00F C00E H00E 119.6 . . ?
C00E C00F H00F 120.2 . . ?
C00E C00F C00H 119.6(6) . . ?
C00H C00F H00F 120.2 . . ?
C006 C00G H00G 119.2 . . ?
C00H C00G C006 121.6(7) . . ?
C00H C00G H00G 119.2 . . ?
C00F C00H C00G 120.2(7) . . ?
C00F C00H H00H 119.9 . . ?
C00G C00H H00H 119.9 . . ?
C008 C00I H00C 109.5 . . ?
C008 C00I H00I 109.5 . . ?
C008 C00I H00J 109.5 . . ?
H00C C00I H00I 109.5 . . ?
H00C C00I H00J 109.5 . . ?
H00I C00I H00J 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S001 C004 C00A C00B 177.8(5) . . . . ?
O002 C007 C00C S001 -175.5(6) . . . . ?
O002 C007 C00C C009 5.6(11) . . . . ?
C003 C004 C00A C00B -2.3(11) . . . . ?
C003 C005 C008 C00B -2.7(10) . . . . ?
C003 C005 C008 C00I 178.1(6) . . . . ?
C003 C007 C00C S001 4.1(7) . . . . ?
C003 C007 C00C C009 -174.8(6) . . . . ?
C004 S001 C00C C007 -2.9(5) . . . . ?
C004 S001 C00C C009 175.9(7) . . . . ?
C004 C003 C005 C008 0.9(10) . . . . ?
C004 C003 C007 O002 176.1(6) . . . . ?
C004 C003 C007 C00C -3.5(8) . . . . ?
C004 C00A C00B C008 0.4(11) . . . . ?
C005 C003 C004 S001 -178.3(5) . . . . ?
C005 C003 C004 C00A 1.7(10) . . . . ?
C005 C003 C007 O002 -4.3(11) . . . . ?
C005 C003 C007 C00C 176.1(6) . . . . ?
C005 C008 C00B C00A 2.1(10) . . . . ?
C006 C009 C00C S001 1.2(11) . . . . ?
C006 C009 C00C C007 179.9(6) . . . . ?
C006 C00D C00E C00F -0.7(12) . . . . ?
C006 C00G C00H C00F -1.2(11) . . . . ?
C007 C003 C004 S001 1.3(7) . . . . ?
C007 C003 C004 C00A -178.7(6) . . . . ?
C007 C003 C005 C008 -178.7(6) . . . . ?
C009 C006 C00D C00E 179.2(7) . . . . ?
C009 C006 C00G C00H -178.4(6) . . . . ?
C00C S001 C004 C003 1.0(5) . . . . ?
C00C S001 C004 C00A -179.0(6) . . . . ?
C00D C006 C009 C00C -4.1(11) . . . . ?
C00D C006 C00G C00H 1.1(10) . . . . ?
C00D C00E C00F C00H 0.6(12) . . . . ?
C00E C00F C00H C00G 0.3(11) . . . . ?
C00G C006 C009 C00C 175.3(7) . . . . ?
C00G C006 C00D C00E -0.2(10) . . . . ?
C00I C008 C00B C00A -178.7(7) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.970
_oxdiff_exptl_absorpt_empirical_full_min 0.585
####################################################################### 
# 
# 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 1545831'
_audit_update_record             
;
2017-04-25 deposited with the CCDC.
2017-09-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H15 Br O3 S'
_chemical_formula_weight         415.29

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   8.811(4)
_cell_length_b                   7.488(4)
_cell_length_c                   13.687(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.942(12)
_cell_angle_gamma                90.00
_cell_volume                     859.1(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    3422
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420
_exptl_absorpt_coefficient_mu    2.530
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6316
_exptl_absorpt_correction_T_max  0.7511
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 5.814
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8802
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_sigmaI/netI    0.0421
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.13
_diffrn_reflns_theta_max         27.60
_reflns_number_total             3576
_reflns_number_gt                3347
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'

_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 > 2sigma(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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0261P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_number_reflns         3576
_refine_ls_number_parameters     228
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0238
_refine_ls_wR_factor_ref         0.0561
_refine_ls_wR_factor_gt          0.0559
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.20161(3) 0.35398(4) 0.183518(15) 0.02870(8) Uani 1 1 d . . .
S1 S 0.42477(6) 0.47709(8) 0.66735(4) 0.01650(12) Uani 1 1 d . . .
O1 O 0.02290(16) 0.2261(2) 0.54295(11) 0.0151(3) Uani 1 1 d . . .
O2 O 0.1214(2) 0.3997(3) 0.93727(12) 0.0332(6) Uani 1 1 d . . .
O3 O -0.13981(18) 0.3808(3) 0.85697(11) 0.0261(4) Uani 1 1 d . . .
C1 C 0.3864(2) 0.4473(3) 0.53581(16) 0.0149(4) Uani 1 1 d . . .
C2 C 0.4798(3) 0.5014(3) 0.47482(18) 0.0197(5) Uani 1 1 d . . .
H2 H 0.5795 0.5587 0.5049 0.024 Uiso 1 1 calc R . .
C3 C 0.4249(3) 0.4703(4) 0.37046(18) 0.0212(5) Uani 1 1 d . . .
H3 H 0.4862 0.5074 0.3278 0.025 Uiso 1 1 calc R . .
C4 C 0.2786(2) 0.3839(4) 0.32775(15) 0.0192(5) Uani 1 1 d . . .
C5 C 0.1860(2) 0.3269(3) 0.38690(15) 0.0152(5) Uani 1 1 d . . .
H5 H 0.0877 0.2671 0.3564 0.018 Uiso 1 1 calc R . .
C6 C 0.2402(2) 0.3591(4) 0.49239(13) 0.0141(4) Uani 1 1 d . . .
C7 C 0.1645(2) 0.3189(3) 0.56885(15) 0.0129(5) Uani 1 1 d . . .
C8 C 0.2469(2) 0.3708(4) 0.66444(14) 0.0142(4) Uani 1 1 d . . .
C9 C 0.2096(2) 0.3329(4) 0.76339(14) 0.0137(4) Uani 1 1 d . . .
H9 H 0.2715 0.4211 0.8153 0.016 Uiso 1 1 calc R . .
C10 C 0.0350(2) 0.3556(4) 0.75619(13) 0.0144(4) Uani 1 1 d . . .
C11 C -0.0922(2) 0.3519(4) 0.67300(14) 0.0158(4) Uani 1 1 d . . .
H11 H -0.1910 0.3706 0.6858 0.019 Uiso 1 1 calc R . .
C12 C -0.1055(2) 0.3234(3) 0.56243(15) 0.0159(5) Uani 1 1 d . . .
H12A H -0.2063 0.2589 0.5292 0.019 Uiso 1 1 calc R . .
H12B H -0.1133 0.4416 0.5289 0.019 Uiso 1 1 calc R . .
C13 C 0.2723(2) 0.1480(3) 0.80244(15) 0.0137(4) Uani 1 1 d . . .
C14 C 0.1867(3) -0.0055(4) 0.76270(19) 0.0227(5) Uani 1 1 d . . .
H14 H 0.0855 0.0049 0.7119 0.027 Uiso 1 1 calc R . .
C15 C 0.2465(3) -0.1725(4) 0.79603(19) 0.0264(6) Uani 1 1 d . . .
H15 H 0.1857 -0.2759 0.7688 0.032 Uiso 1 1 calc R . .
C16 C 0.3949(3) -0.1905(3) 0.86905(17) 0.0211(5) Uani 1 1 d . . .
H16 H 0.4366 -0.3056 0.8913 0.025 Uiso 1 1 calc R . .
C17 C 0.4808(3) -0.0400(4) 0.90887(16) 0.0186(5) Uani 1 1 d . . .
H17 H 0.5823 -0.0511 0.9593 0.022 Uiso 1 1 calc R . .
C18 C 0.4199(3) 0.1289(3) 0.87578(16) 0.0167(5) Uani 1 1 d . . .
H18 H 0.4804 0.2321 0.9039 0.020 Uiso 1 1 calc R . .
C19 C 0.0124(2) 0.3808(4) 0.85981(16) 0.0183(5) Uani 1 1 d . . .
C20 C -0.1694(3) 0.4065(4) 0.95441(19) 0.0361(8) Uani 1 1 d . . .
H20A H -0.1456 0.2957 0.9944 0.054 Uiso 1 1 calc R . .
H20B H -0.2816 0.4384 0.9422 0.054 Uiso 1 1 calc R . .
H20C H -0.1011 0.5026 0.9926 0.054 Uiso 1 1 calc R . .


_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
Br1 C4 1.893(2) . ?
S1 C1 1.741(2) . ?
S1 C8 1.748(2) . ?
O1 C7 1.376(2) . ?
O1 C12 1.438(2) . ?
O2 C19 1.200(3) . ?
O3 C19 1.330(3) . ?
O3 C20 1.448(3) . ?
C1 C2 1.400(3) . ?
C1 C6 1.406(3) . ?
C2 C3 1.379(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.399(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(3) . ?
C5 C6 1.395(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.435(3) . ?
C7 C8 1.343(3) . ?
C8 C9 1.515(3) . ?
C9 C10 1.521(3) . ?
C9 C13 1.525(4) . ?
C9 H9 1.0000 . ?
C10 C11 1.330(3) . ?
C10 C19 1.503(3) . ?
C11 C12 1.497(3) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C18 1.384(3) . ?
C13 C14 1.390(3) . ?
C14 C15 1.379(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.386(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.373(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.394(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
C1 S1 C8 91.78(10) . . ?
C7 O1 C12 113.51(17) . . ?
C19 O3 C20 116.05(18) . . ?
C2 C1 C6 120.9(2) . . ?
C2 C1 S1 128.10(18) . . ?
C6 C1 S1 110.98(15) . . ?
C3 C2 C1 119.1(2) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 119.6(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 122.2(2) . . ?
C5 C4 Br1 119.18(17) . . ?
C3 C4 Br1 118.60(16) . . ?
C4 C5 C6 118.5(2) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C5 C6 C1 119.72(18) . . ?
C5 C6 C7 129.1(2) . . ?
C1 C6 C7 111.18(17) . . ?
C8 C7 O1 124.86(18) . . ?
C8 C7 C6 114.64(19) . . ?
O1 C7 C6 120.42(17) . . ?
C7 C8 C9 128.0(2) . . ?
C7 C8 S1 111.42(15) . . ?
C9 C8 S1 120.30(14) . . ?
C8 C9 C10 114.48(16) . . ?
C8 C9 C13 109.18(19) . . ?
C10 C9 C13 112.0(2) . . ?
C8 C9 H9 106.9 . . ?
C10 C9 H9 106.9 . . ?
C13 C9 H9 106.9 . . ?
C11 C10 C19 119.27(17) . . ?
C11 C10 C9 128.50(17) . . ?
C19 C10 C9 112.22(16) . . ?
C10 C11 C12 130.66(17) . . ?
C10 C11 H11 114.7 . . ?
C12 C11 H11 114.7 . . ?
O1 C12 C11 116.04(17) . . ?
O1 C12 H12A 108.3 . . ?
C11 C12 H12A 108.3 . . ?
O1 C12 H12B 108.3 . . ?
C11 C12 H12B 108.3 . . ?
H12A C12 H12B 107.4 . . ?
C18 C13 C14 118.3(2) . . ?
C18 C13 C9 120.4(2) . . ?
C14 C13 C9 121.26(19) . . ?
C15 C14 C13 120.9(2) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 120.4(2) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C17 C16 C15 119.2(2) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C16 C17 C18 120.4(2) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C13 C18 C17 120.7(2) . . ?
C13 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
O2 C19 O3 123.46(19) . . ?
O2 C19 C10 123.10(19) . . ?
O3 C19 C10 113.43(17) . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 S1 C1 C2 179.5(2) . . . . ?
C8 S1 C1 C6 0.4(2) . . . . ?
C6 C1 C2 C3 1.3(4) . . . . ?
S1 C1 C2 C3 -177.69(19) . . . . ?
C1 C2 C3 C4 -0.7(4) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C2 C3 C4 Br1 176.8(2) . . . . ?
C3 C4 C5 C6 0.8(4) . . . . ?
Br1 C4 C5 C6 -176.36(19) . . . . ?
C4 C5 C6 C1 -0.2(4) . . . . ?
C4 C5 C6 C7 177.8(3) . . . . ?
C2 C1 C6 C5 -0.9(4) . . . . ?
S1 C1 C6 C5 178.3(2) . . . . ?
C2 C1 C6 C7 -179.2(2) . . . . ?
S1 C1 C6 C7 0.0(3) . . . . ?
C12 O1 C7 C8 63.5(3) . . . . ?
C12 O1 C7 C6 -120.0(2) . . . . ?
C5 C6 C7 C8 -178.6(3) . . . . ?
C1 C6 C7 C8 -0.5(3) . . . . ?
C5 C6 C7 O1 4.5(4) . . . . ?
C1 C6 C7 O1 -177.4(2) . . . . ?
O1 C7 C8 C9 3.3(4) . . . . ?
C6 C7 C8 C9 -173.3(2) . . . . ?
O1 C7 C8 S1 177.47(16) . . . . ?
C6 C7 C8 S1 0.8(3) . . . . ?
C1 S1 C8 C7 -0.7(2) . . . . ?
C1 S1 C8 C9 174.0(2) . . . . ?
C7 C8 C9 C10 -43.7(4) . . . . ?
S1 C8 C9 C10 142.6(2) . . . . ?
C7 C8 C9 C13 82.7(3) . . . . ?
S1 C8 C9 C13 -91.0(2) . . . . ?
C8 C9 C10 C11 21.6(4) . . . . ?
C13 C9 C10 C11 -103.3(3) . . . . ?
C8 C9 C10 C19 -159.8(2) . . . . ?
C13 C9 C10 C19 75.2(3) . . . . ?
C19 C10 C11 C12 -177.8(3) . . . . ?
C9 C10 C11 C12 0.7(6) . . . . ?
C7 O1 C12 C11 -69.4(2) . . . . ?
C10 C11 C12 O1 24.4(4) . . . . ?
C8 C9 C13 C18 96.2(2) . . . . ?
C10 C9 C13 C18 -135.99(19) . . . . ?
C8 C9 C13 C14 -81.1(2) . . . . ?
C10 C9 C13 C14 46.7(3) . . . . ?
C18 C13 C14 C15 0.5(3) . . . . ?
C9 C13 C14 C15 177.9(2) . . . . ?
C13 C14 C15 C16 -0.9(4) . . . . ?
C14 C15 C16 C17 0.8(4) . . . . ?
C15 C16 C17 C18 -0.4(3) . . . . ?
C14 C13 C18 C17 -0.1(3) . . . . ?
C9 C13 C18 C17 -177.43(19) . . . . ?
C16 C17 C18 C13 0.0(3) . . . . ?
C20 O3 C19 O2 0.3(4) . . . . ?
C20 O3 C19 C10 -179.4(2) . . . . ?
C11 C10 C19 O2 -173.9(3) . . . . ?
C9 C10 C19 O2 7.4(4) . . . . ?
C11 C10 C19 O3 5.8(4) . . . . ?
C9 C10 C19 O3 -172.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.60
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.055
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1546413'
_audit_update_record             
;
2017-04-26 deposited with the CCDC.
2017-09-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H15 Cl O5 S'
_chemical_formula_weight         402.83

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'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'

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'

_cell_length_a                   9.7083(11)
_cell_length_b                   13.4391(12)
_cell_length_c                   14.4317(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.335(10)
_cell_angle_gamma                90.00
_cell_volume                     1863.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2821
_cell_measurement_theta_min      2.8310
_cell_measurement_theta_max      30.1150

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    0.346
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7649
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3634
_reflns_number_gt                2998
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2sigma(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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0669P)²+22.0807P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3634
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1377
_refine_ls_R_factor_gt           0.1255
_refine_ls_wR_factor_ref         0.3277
_refine_ls_wR_factor_gt          0.3213
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_restrained_S_all      1.155
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.87570(18) 0.44757(13) 0.71096(11) 0.0419(4) Uani 1 1 d . . .
Cl1 Cl 0.9621(2) 0.78562(15) 0.43313(15) 0.0610(5) Uani 1 1 d . . .
O3 O 0.6642(5) 0.4454(3) 0.4614(3) 0.0436(12) Uani 1 1 d . . .
O1 O 0.7609(6) 0.0948(4) 0.6395(3) 0.0527(13) Uani 1 1 d . . .
O4 O 0.9869(6) 0.3777(4) 0.7338(4) 0.0620(15) Uani 1 1 d . . .
O5 O 0.8113(6) 0.4860(4) 0.7876(3) 0.0630(16) Uani 1 1 d . . .
C3 C 0.6605(7) 0.2333(5) 0.5536(4) 0.0370(15) Uani 1 1 d . . .
C15 C 0.8405(7) 0.5425(5) 0.5526(4) 0.0366(14) Uani 1 1 d . . .
O2 O 0.6908(8) 0.0765(4) 0.4869(4) 0.080(2) Uani 1 1 d . . .
C2 C 0.7115(7) 0.1292(5) 0.5653(4) 0.0385(15) Uani 1 1 d . . .
C8 C 0.6834(6) 0.2981(4) 0.6414(4) 0.0351(14) Uani 1 1 d . . .
H8 H 0.7514 0.2629 0.6866 0.042 Uiso 1 1 calc R . .
C9 C 0.5516(7) 0.3060(5) 0.6859(4) 0.0396(15) Uani 1 1 d . . .
C20 C 0.8526(7) 0.6143(5) 0.4869(5) 0.0408(15) Uani 1 1 d . . .
H20 H 0.8004 0.6116 0.4276 0.049 Uiso 1 1 calc R . .
C7 C 0.7503(6) 0.3972(4) 0.6223(4) 0.0341(14) Uani 1 1 d . . .
C14 C 0.4999(8) 0.3950(6) 0.7170(5) 0.055(2) Uani 1 1 d . . .
H14 H 0.5470 0.4541 0.7098 0.066 Uiso 1 1 calc R . .
C6 C 0.7439(6) 0.4554(5) 0.5454(4) 0.0371(14) Uani 1 1 d . . .
C10 C 0.4772(8) 0.2187(6) 0.6991(5) 0.0509(18) Uani 1 1 d . . .
H10 H 0.5092 0.1578 0.6803 0.061 Uiso 1 1 calc R . .
C16 C 0.9211(7) 0.5457(5) 0.6413(4) 0.0427(16) Uani 1 1 d . . .
C5 C 0.5508(7) 0.3736(5) 0.4583(5) 0.0467(18) Uani 1 1 d . . .
H5A H 0.4906 0.3793 0.3987 0.056 Uiso 1 1 calc R . .
H5B H 0.4958 0.3889 0.5075 0.056 Uiso 1 1 calc R . .
C4 C 0.6034(7) 0.2689(5) 0.4704(4) 0.0443(17) Uani 1 1 d . . .
H4 H 0.5961 0.2275 0.4183 0.053 Uiso 1 1 calc R . .
C19 C 0.9470(7) 0.6922(5) 0.5127(5) 0.0460(17) Uani 1 1 d . . .
C11 C 0.3572(8) 0.2224(7) 0.7397(6) 0.060(2) Uani 1 1 d . . .
H11 H 0.3081 0.1641 0.7466 0.071 Uiso 1 1 calc R . .
C17 C 1.0146(8) 0.6215(6) 0.6658(5) 0.055(2) Uani 1 1 d . . .
H17 H 1.0689 0.6231 0.7245 0.065 Uiso 1 1 calc R . .
C18 C 1.0253(9) 0.6957(6) 0.5997(5) 0.056(2) Uani 1 1 d . . .
H18 H 1.0864 0.7485 0.6149 0.068 Uiso 1 1 calc R . .
C13 C 0.3815(8) 0.3967(7) 0.7577(6) 0.065(2) Uani 1 1 d . . .
H13 H 0.3493 0.4572 0.7774 0.078 Uiso 1 1 calc R . .
C12 C 0.3088(8) 0.3115(8) 0.7702(5) 0.064(2) Uani 1 1 d . . .
H12 H 0.2288 0.3136 0.7985 0.077 Uiso 1 1 calc R . .
C1 C 0.7361(15) -0.0269(7) 0.4937(7) 0.104(4) Uani 1 1 d . . .
H1A H 0.7122 -0.0588 0.4340 0.155 Uiso 1 1 calc R . .
H1B H 0.6908 -0.0607 0.5396 0.155 Uiso 1 1 calc R . .
H1C H 0.8351 -0.0295 0.5121 0.155 Uiso 1 1 calc R . .


_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 O4 1.432(5) . ?
S1 O5 1.442(5) . ?
S1 C16 1.753(7) . ?
S1 C7 1.768(6) . ?
Cl1 C19 1.722(7) . ?
O3 C6 1.347(7) . ?
O3 C5 1.460(8) . ?
O1 C2 1.201(8) . ?
C3 C4 1.337(9) . ?
C3 C2 1.486(9) . ?
C3 C8 1.527(8) . ?
C15 C20 1.370(9) . ?
C15 C16 1.400(8) . ?
C15 C6 1.495(9) . ?
O2 C2 1.325(8) . ?
O2 C1 1.457(10) . ?
C8 C9 1.517(9) . ?
C8 C7 1.524(9) . ?
C8 H8 0.9800 . ?
C9 C14 1.396(10) . ?
C9 C10 1.405(10) . ?
C20 C19 1.405(9) . ?
C20 H20 0.9300 . ?
C7 C6 1.351(9) . ?
C14 C13 1.365(11) . ?
C14 H14 0.9300 . ?
C10 C11 1.378(11) . ?
C10 H10 0.9300 . ?
C16 C17 1.376(10) . ?
C5 C4 1.498(10) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C4 H4 0.9300 . ?
C19 C18 1.372(10) . ?
C11 C12 1.381(13) . ?
C11 H11 0.9300 . ?
C17 C18 1.395(11) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C13 C12 1.370(13) . ?
C13 H13 0.9300 . ?
C12 H12 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

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
O4 S1 O5 117.0(3) . . ?
O4 S1 C16 112.4(4) . . ?
O5 S1 C16 110.1(3) . . ?
O4 S1 C7 109.4(3) . . ?
O5 S1 C7 111.2(3) . . ?
C16 S1 C7 94.4(3) . . ?
C6 O3 C5 115.2(5) . . ?
C4 C3 C2 121.8(6) . . ?
C4 C3 C8 122.2(6) . . ?
C2 C3 C8 115.9(5) . . ?
C20 C15 C16 121.2(6) . . ?
C20 C15 C6 128.3(6) . . ?
C16 C15 C6 110.5(6) . . ?
C2 O2 C1 116.4(6) . . ?
O1 C2 O2 123.2(6) . . ?
O1 C2 C3 123.1(6) . . ?
O2 C2 C3 113.6(5) . . ?
C9 C8 C7 115.0(5) . . ?
C9 C8 C3 111.1(5) . . ?
C7 C8 C3 111.3(5) . . ?
C9 C8 H8 106.2 . . ?
C7 C8 H8 106.2 . . ?
C3 C8 H8 106.2 . . ?
C14 C9 C10 117.1(7) . . ?
C14 C9 C8 124.1(6) . . ?
C10 C9 C8 118.8(6) . . ?
C15 C20 C19 117.4(6) . . ?
C15 C20 H20 121.3 . . ?
C19 C20 H20 121.3 . . ?
C6 C7 C8 133.2(5) . . ?
C6 C7 S1 108.5(5) . . ?
C8 C7 S1 118.1(4) . . ?
C13 C14 C9 121.2(8) . . ?
C13 C14 H14 119.4 . . ?
C9 C14 H14 119.4 . . ?
O3 C6 C7 129.3(6) . . ?
O3 C6 C15 114.4(5) . . ?
C7 C6 C15 116.3(5) . . ?
C11 C10 C9 120.7(7) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C17 C16 C15 121.2(6) . . ?
C17 C16 S1 128.3(5) . . ?
C15 C16 S1 110.3(5) . . ?
O3 C5 C4 112.0(6) . . ?
O3 C5 H5A 109.2 . . ?
C4 C5 H5A 109.2 . . ?
O3 C5 H5B 109.2 . . ?
C4 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C3 C4 C5 122.1(6) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C18 C19 C20 121.4(7) . . ?
C18 C19 Cl1 119.7(6) . . ?
C20 C19 Cl1 118.8(5) . . ?
C10 C11 C12 120.9(8) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C16 C17 C18 117.7(6) . . ?
C16 C17 H17 121.2 . . ?
C18 C17 H17 121.2 . . ?
C19 C18 C17 121.0(7) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C14 C13 C12 121.6(9) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C12 C11 118.5(7) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.139
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.129
