# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_2R_3R-14j
_database_code_depnum_ccdc_archive 'CCDC 1529450'
_audit_update_record             
;
2017-01-24 deposited with the CCDC.
2017-02-28 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C12 H14 O3 S'
_chemical_formula_sum            'C12 H14 O3 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         238.29
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   11.8164(18)
_cell_length_b                   9.2321(11)
_cell_length_c                   11.9043(19)
_cell_angle_alpha                90
_cell_angle_beta                 110.492(3)
_cell_angle_gamma                90
_cell_volume                     1216.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3948
_cell_measurement_theta_min      3.0156
_cell_measurement_theta_max      22.7146
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       Needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.160
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504

_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.6041
_exptl_absorpt_correction_T_max  0.7454

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              Bruker

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEX II DUO'
_diffrn_measurement_method       'φ & ω  scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            13855
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_full        26.38
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_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.
;

_reflns_number_total             4845
_reflns_number_gt                3941
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1063
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_number_reflns         4845
_refine_ls_number_parameters     291
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0574P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.208
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 1478 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(4)

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_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
C C1 0.3348(3) 0.6058(4) 0.9303(3) 0.0447(8) Uani d . . . 1 . .
H H1 0.3735 0.513 0.9265 0.054 Uiso calc U . R 1 . .
C C2 0.2894(3) 0.6776(4) 0.8049(3) 0.0473(8) Uani d . . . 1 . .
H H2 0.293 0.7828 0.8161 0.057 Uiso calc U . R 1 . .
C C3 0.1562(3) 0.6331(5) 0.7538(3) 0.0559(9) Uani d . . . 1 . .
H H3A 0.1095 0.7029 0.6949 0.067 Uiso calc U . R 1 . .
H H3B 0.1473 0.5385 0.7163 0.067 Uiso calc U . R 1 . .
C C4 0.1154(3) 0.6298(5) 0.8610(3) 0.0600(10) Uani d . . . 1 . .
H H4A 0.0899 0.7253 0.8764 0.072 Uiso calc U . R 1 . .
H H4B 0.0487 0.5629 0.8475 0.072 Uiso calc U . R 1 . .
C C5 0.2230(3) 0.5808(4) 0.9634(3) 0.0506(9) Uani d . . . 1 . .
S S6 0.43933(9) 0.72158(10) 1.03900(9) 0.0548(3) Uani d . . . 1 . .
O O7 0.3700(3) 0.8276(3) 1.0748(3) 0.0821(10) Uani d . . . 1 . .
O O8 0.5278(3) 0.7716(3) 0.9913(3) 0.0760(9) Uani d . . . 1 . .
C C9 0.5106(4) 0.6071(5) 1.1612(4) 0.0719(12) Uani d . . . 1 . .
H H9A 0.554 0.5327 1.1369 0.108 Uiso calc U . R 1 . .
H H9B 0.4508 0.5635 1.1881 0.108 Uiso calc U . R 1 . .
H H9C 0.5659 0.6625 1.2253 0.108 Uiso calc U . R 1 . .
C C10 0.3617(3) 0.6394(5) 0.7265(3) 0.0543(9) Uani d . . . 1 . .
C C11 0.4197(5) 0.7417(6) 0.6844(4) 0.0855(16) Uani d . . . 1 . .
H H11 0.4136 0.8387 0.7027 0.103 Uiso calc U . R 1 . .
C C12 0.4891(6) 0.7033(9) 0.6135(5) 0.0991(18) Uani d . . . 1 . .
H H12 0.529 0.7745 0.5865 0.119 Uiso calc U . R 1 . .
C C13 0.4975(5) 0.5637(9) 0.5851(5) 0.0994(19) Uani d . . . 1 . .
H H13 0.5443 0.5388 0.5394 0.119 Uiso calc U . R 1 . .
C C14 0.4379(5) 0.4585(7) 0.6226(5) 0.0883(17) Uani d . . . 1 . .
H H14 0.4425 0.3626 0.6008 0.106 Uiso calc U . R 1 . .
C C15 0.3707(5) 0.4943(5) 0.6932(4) 0.0707(12) Uani d . . . 1 . .
H H15 0.3308 0.4218 0.719 0.085 Uiso calc U . R 1 . .
O O16 0.2245(3) 0.5307(3) 1.0571(3) 0.0707(8) Uani d . . . 1 . .
C C17 0.0188(3) 0.6216(4) 0.1729(3) 0.0467(8) Uani d . . . 1 . .
H H17 0.0323 0.541 0.1255 0.056 Uiso calc U . R 1 . .
C C18 0.0921(4) 0.5974(4) 0.3065(3) 0.0543(9) Uani d . . . 1 . .
H H18 0.0505 0.6477 0.3534 0.065 Uiso calc U . R 1 . .
C C19 0.2118(4) 0.6793(5) 0.3240(4) 0.0746(13) Uani d . . . 1 . .
H H19A 0.2508 0.7079 0.4071 0.089 Uiso calc U . R 1 . .
H H19B 0.267 0.6191 0.3005 0.089 Uiso calc U . R 1 . .
C C20 0.1745(5) 0.8114(5) 0.2435(5) 0.0838(14) Uani d . . . 1 . .
H H20A 0.1524 0.8906 0.2853 0.101 Uiso calc U . R 1 . .
H H20B 0.2398 0.8429 0.2177 0.101 Uiso calc U . R 1 . .
C C21 0.0681(4) 0.7636(4) 0.1384(4) 0.0559(10) Uani d . . . 1 . .
S S22 -0.13930(9) 0.63894(9) 0.14721(8) 0.0499(2) Uani d . . . 1 . .
O O23 -0.1750(3) 0.5148(4) 0.1990(3) 0.0714(8) Uani d . . . 1 . .
O O24 -0.1582(3) 0.7786(3) 0.1913(3) 0.0637(8) Uani d . . . 1 . .
C C25 -0.2098(4) 0.6346(5) -0.0086(3) 0.0642(10) Uani d . . . 1 . .
H H25A -0.195 0.5427 -0.0386 0.096 Uiso calc U . R 1 . .
H H25B -0.1779 0.7106 -0.0439 0.096 Uiso calc U . R 1 . .
H H25C -0.2952 0.6481 -0.029 0.096 Uiso calc U . R 1 . .
C C26 0.1141(3) 0.4427(4) 0.3507(3) 0.0489(9) Uani d . . . 1 . .
C C27 0.1618(4) 0.3441(4) 0.2936(4) 0.0579(10) Uani d . . . 1 . .
H H27 0.1747 0.3703 0.2236 0.07 Uiso calc U . R 1 . .
C C28 0.1912(4) 0.2045(5) 0.3398(4) 0.0719(12) Uani d . . . 1 . .
H H28 0.2218 0.1377 0.2994 0.086 Uiso calc U . R 1 . .
C C29 0.1757(5) 0.1663(6) 0.4422(5) 0.0799(14) Uani d . . . 1 . .
H H29 0.1976 0.074 0.4735 0.096 Uiso calc U . R 1 . .
C C30 0.1277(5) 0.2623(7) 0.5005(4) 0.0856(18) Uani d . . . 1 . .
H H30 0.1165 0.2351 0.5711 0.103 Uiso calc U . R 1 . .
C C31 0.0955(4) 0.4011(6) 0.4543(3) 0.0687(12) Uani d . . . 1 . .
H H31 0.0615 0.4657 0.4933 0.082 Uiso calc U . R 1 . .
O O32 0.0284(3) 0.8227(3) 0.0437(3) 0.0700(8) Uani d . . . 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
C1 C5 . 1.523(5) ?
C1 C2 . 1.547(5) ?
C1 S6 . 1.795(3) ?
C1 H1 . 0.98 ?
C2 C10 . 1.511(5) ?
C2 C3 . 1.532(5) ?
C2 H2 . 0.98 ?
C3 C4 . 1.513(5) ?
C3 H3A . 0.97 ?
C3 H3B . 0.97 ?
C4 C5 . 1.491(6) ?
C4 H4A . 0.97 ?
C4 H4B . 0.97 ?
C5 O16 . 1.202(4) ?
S6 O8 . 1.429(3) ?
S6 O7 . 1.434(3) ?
S6 C9 . 1.756(4) ?
C9 H9A . 0.96 ?
C9 H9B . 0.96 ?
C9 H9C . 0.96 ?
C10 C11 . 1.362(6) ?
C10 C15 . 1.411(6) ?
C11 C12 . 1.412(8) ?
C11 H11 . 0.93 ?
C12 C13 . 1.344(9) ?
C12 H12 . 0.93 ?
C13 C14 . 1.364(8) ?
C13 H13 . 0.93 ?
C14 C15 . 1.383(6) ?
C14 H14 . 0.93 ?
C15 H15 . 0.93 ?
C17 C18 . 1.538(5) ?
C17 C21 . 1.547(5) ?
C17 S22 . 1.792(4) ?
C17 H17 . 0.98 ?
C18 C26 . 1.513(6) ?
C18 C19 . 1.552(6) ?
C18 H18 . 0.98 ?
C19 C20 . 1.517(7) ?
C19 H19A . 0.97 ?
C19 H19B . 0.97 ?
C20 C21 . 1.496(6) ?
C20 H20A . 0.97 ?
C20 H20B . 0.97 ?
C21 O32 . 1.191(5) ?
S22 O23 . 1.434(3) ?
S22 O24 . 1.439(3) ?
S22 C25 . 1.748(4) ?
C25 H25A . 0.96 ?
C25 H25B . 0.96 ?
C25 H25C . 0.96 ?
C26 C27 . 1.370(5) ?
C26 C31 . 1.380(5) ?
C27 C28 . 1.396(6) ?
C27 H27 . 0.93 ?
C28 C29 . 1.342(7) ?
C28 H28 . 0.93 ?
C29 C30 . 1.365(7) ?
C29 H29 . 0.93 ?
C30 C31 . 1.394(8) ?
C30 H30 . 0.93 ?
C31 H31 . 0.93 ?

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
C5 C1 C2 . . 106.0(3) ?
C5 C1 S6 . . 110.1(2) ?
C2 C1 S6 . . 111.1(2) ?
C5 C1 H1 . . 109.9 ?
C2 C1 H1 . . 109.9 ?
S6 C1 H1 . . 109.9 ?
C10 C2 C3 . . 114.6(3) ?
C10 C2 C1 . . 114.6(3) ?
C3 C2 C1 . . 103.3(3) ?
C10 C2 H2 . . 108.0 ?
C3 C2 H2 . . 108.0 ?
C1 C2 H2 . . 108.0 ?
C4 C3 C2 . . 104.9(3) ?
C4 C3 H3A . . 110.8 ?
C2 C3 H3A . . 110.8 ?
C4 C3 H3B . . 110.8 ?
C2 C3 H3B . . 110.8 ?
H3A C3 H3B . . 108.8 ?
C5 C4 C3 . . 105.3(3) ?
C5 C4 H4A . . 110.7 ?
C3 C4 H4A . . 110.7 ?
C5 C4 H4B . . 110.7 ?
C3 C4 H4B . . 110.7 ?
H4A C4 H4B . . 108.8 ?
O16 C5 C4 . . 127.4(4) ?
O16 C5 C1 . . 124.5(4) ?
C4 C5 C1 . . 108.1(3) ?
O8 S6 O7 . . 118.1(2) ?
O8 S6 C9 . . 108.6(2) ?
O7 S6 C9 . . 108.9(2) ?
O8 S6 C1 . . 108.68(18) ?
O7 S6 C1 . . 107.46(18) ?
C9 S6 C1 . . 104.4(2) ?
S6 C9 H9A . . 109.5 ?
S6 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
S6 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C11 C10 C15 . . 117.3(4) ?
C11 C10 C2 . . 122.1(4) ?
C15 C10 C2 . . 120.6(4) ?
C10 C11 C12 . . 121.2(5) ?
C10 C11 H11 . . 119.4 ?
C12 C11 H11 . . 119.4 ?
C13 C12 C11 . . 120.1(6) ?
C13 C12 H12 . . 120.0 ?
C11 C12 H12 . . 120.0 ?
C12 C13 C14 . . 120.5(6) ?
C12 C13 H13 . . 119.7 ?
C14 C13 H13 . . 119.7 ?
C13 C14 C15 . . 120.1(6) ?
C13 C14 H14 . . 120.0 ?
C15 C14 H14 . . 120.0 ?
C14 C15 C10 . . 120.8(5) ?
C14 C15 H15 . . 119.6 ?
C10 C15 H15 . . 119.6 ?
C18 C17 C21 . . 105.6(3) ?
C18 C17 S22 . . 111.4(2) ?
C21 C17 S22 . . 110.2(3) ?
C18 C17 H17 . . 109.8 ?
C21 C17 H17 . . 109.8 ?
S22 C17 H17 . . 109.8 ?
C26 C18 C17 . . 117.6(3) ?
C26 C18 C19 . . 112.1(4) ?
C17 C18 C19 . . 103.0(3) ?
C26 C18 H18 . . 107.9 ?
C17 C18 H18 . . 107.9 ?
C19 C18 H18 . . 107.9 ?
C20 C19 C18 . . 104.9(4) ?
C20 C19 H19A . . 110.8 ?
C18 C19 H19A . . 110.8 ?
C20 C19 H19B . . 110.8 ?
C18 C19 H19B . . 110.8 ?
H19A C19 H19B . . 108.8 ?
C21 C20 C19 . . 105.4(4) ?
C21 C20 H20A . . 110.7 ?
C19 C20 H20A . . 110.7 ?
C21 C20 H20B . . 110.7 ?
C19 C20 H20B . . 110.7 ?
H20A C20 H20B . . 108.8 ?
O32 C21 C20 . . 126.4(4) ?
O32 C21 C17 . . 125.4(4) ?
C20 C21 C17 . . 108.2(4) ?
O23 S22 O24 . . 116.92(18) ?
O23 S22 C25 . . 109.6(2) ?
O24 S22 C25 . . 109.3(2) ?
O23 S22 C17 . . 107.57(18) ?
O24 S22 C17 . . 107.66(17) ?
C25 S22 C17 . . 105.08(18) ?
S22 C25 H25A . . 109.5 ?
S22 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
S22 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?
C27 C26 C31 . . 118.7(4) ?
C27 C26 C18 . . 120.4(3) ?
C31 C26 C18 . . 120.8(4) ?
C26 C27 C28 . . 120.4(4) ?
C26 C27 H27 . . 119.8 ?
C28 C27 H27 . . 119.8 ?
C29 C28 C27 . . 120.4(5) ?
C29 C28 H28 . . 119.8 ?
C27 C28 H28 . . 119.8 ?
C28 C29 C30 . . 120.2(5) ?
C28 C29 H29 . . 119.9 ?
C30 C29 H29 . . 119.9 ?
C29 C30 C31 . . 120.1(4) ?
C29 C30 H30 . . 120.0 ?
C31 C30 H30 . . 120.0 ?
C26 C31 C30 . . 120.1(5) ?
C26 C31 H31 . . 119.9 ?
C30 C31 H31 . . 119.9 ?

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
C5 C1 C2 C10 . . . . -147.7(3) ?
S6 C1 C2 C10 . . . . 92.7(3) ?
C5 C1 C2 C3 . . . . -22.3(4) ?
S6 C1 C2 C3 . . . . -141.9(3) ?
C10 C2 C3 C4 . . . . 159.8(3) ?
C1 C2 C3 C4 . . . . 34.5(4) ?
C2 C3 C4 C5 . . . . -33.8(4) ?
C3 C4 C5 O16 . . . . -160.9(4) ?
C3 C4 C5 C1 . . . . 19.5(4) ?
C2 C1 C5 O16 . . . . -177.6(4) ?
S6 C1 C5 O16 . . . . -57.3(4) ?
C2 C1 C5 C4 . . . . 2.0(4) ?
S6 C1 C5 C4 . . . . 122.3(3) ?
C5 C1 S6 O8 . . . . -165.9(3) ?
C2 C1 S6 O8 . . . . -48.8(3) ?
C5 C1 S6 O7 . . . . -37.1(3) ?
C2 C1 S6 O7 . . . . 80.0(3) ?
C5 C1 S6 C9 . . . . 78.4(3) ?
C2 C1 S6 C9 . . . . -164.5(3) ?
C3 C2 C10 C11 . . . . 121.1(4) ?
C1 C2 C10 C11 . . . . -119.7(4) ?
C3 C2 C10 C15 . . . . -58.4(5) ?
C1 C2 C10 C15 . . . . 60.8(5) ?
C15 C10 C11 C12 . . . . -2.0(7) ?
C2 C10 C11 C12 . . . . 178.5(5) ?
C10 C11 C12 C13 . . . . 0.9(9) ?
C11 C12 C13 C14 . . . . 1.0(10) ?
C12 C13 C14 C15 . . . . -1.7(9) ?
C13 C14 C15 C10 . . . . 0.5(8) ?
C11 C10 C15 C14 . . . . 1.3(7) ?
C2 C10 C15 C14 . . . . -179.2(4) ?
C21 C17 C18 C26 . . . . -149.1(3) ?
S22 C17 C18 C26 . . . . 91.2(4) ?
C21 C17 C18 C19 . . . . -25.4(4) ?
S22 C17 C18 C19 . . . . -145.1(3) ?
C26 C18 C19 C20 . . . . 163.3(4) ?
C17 C18 C19 C20 . . . . 36.1(4) ?
C18 C19 C20 C21 . . . . -32.8(5) ?
C19 C20 C21 O32 . . . . -162.4(4) ?
C19 C20 C21 C17 . . . . 16.7(5) ?
C18 C17 C21 O32 . . . . -175.0(4) ?
S22 C17 C21 O32 . . . . -54.5(5) ?
C18 C17 C21 C20 . . . . 5.9(4) ?
S22 C17 C21 C20 . . . . 126.4(3) ?
C18 C17 S22 O23 . . . . -53.5(3) ?
C21 C17 S22 O23 . . . . -170.5(3) ?
C18 C17 S22 O24 . . . . 73.3(3) ?
C21 C17 S22 O24 . . . . -43.7(3) ?
C18 C17 S22 C25 . . . . -170.3(3) ?
C21 C17 S22 C25 . . . . 72.8(3) ?
C17 C18 C26 C27 . . . . 52.1(5) ?
C19 C18 C26 C27 . . . . -66.9(5) ?
C17 C18 C26 C31 . . . . -133.0(4) ?
C19 C18 C26 C31 . . . . 108.0(4) ?
C31 C26 C27 C28 . . . . -0.2(6) ?
C18 C26 C27 C28 . . . . 174.8(4) ?
C26 C27 C28 C29 . . . . -1.5(7) ?
C27 C28 C29 C30 . . . . 1.8(7) ?
C28 C29 C30 C31 . . . . -0.5(7) ?
C27 C26 C31 C30 . . . . 1.5(6) ?
C18 C26 C31 C30 . . . . -173.5(4) ?
C29 C30 C31 C26 . . . . -1.2(7) ?

####################################################################### 
# 
# 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_2R_3R-14i
_database_code_depnum_ccdc_archive 'CCDC 1529448'
_audit_update_record             
;
2017-01-24 deposited with the CCDC.
2017-02-28 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C17 H15 Br O3 S'
_chemical_formula_sum            'C17 H15 Br O3 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         379.26
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   7.8117(10)
_cell_length_b                   12.6388(16)
_cell_length_c                   16.816(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1660.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5607
_cell_measurement_theta_min      2.8752
_cell_measurement_theta_max      24.4402
_cell_measurement_temperature    292.(2)

_exptl_crystal_description       Block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768

_exptl_absorpt_coefficient_mu    2.610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.5792
_exptl_absorpt_correction_T_max  0.7455

_exptl_special_details           
;
;

_diffrn_ambient_temperature      292.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              Bruker

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEX II DUO'
_diffrn_measurement_method       'φ & ω  scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            20445
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         27.11
_diffrn_reflns_theta_full        27.11
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21

_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.
;

_reflns_number_total             3628
_reflns_number_gt                3045
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0819
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_number_reflns         3628
_refine_ls_number_parameters     199
_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)+(0.0211P)²+0.6542P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.575
_refine_diff_density_min         -0.510
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 1123 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.018(4)

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'

_computing_data_collection       'Bruker Instrument Service v2010, 1, 0, 0'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_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
C C1 -0.0545(4) 0.3812(3) 0.57342(19) 0.0371(8) Uani d . . . 1 . .
H H1 0.0458 0.3668 0.5401 0.044 Uiso calc U . R 1 . .
C C2 -0.0903(5) 0.5018(3) 0.5735(2) 0.0368(8) Uani d . . . 1 . .
H H2 -0.1454 0.5203 0.6239 0.044 Uiso calc U . R 1 . .
C C3 -0.2236(5) 0.5152(4) 0.5058(3) 0.0521(11) Uani d . . . 1 . .
H H3A -0.294 0.5773 0.5149 0.062 Uiso calc U . R 1 . .
H H3B -0.1669 0.5225 0.4547 0.062 Uiso calc U . R 1 . .
C C4 -0.3325(5) 0.4144(4) 0.5079(3) 0.0536(11) Uani d . . . 1 . .
H H4A -0.4276 0.4224 0.5445 0.064 Uiso calc U . R 1 . .
H H4B -0.3772 0.3982 0.4555 0.064 Uiso calc U . R 1 . .
C C5 -0.2130(5) 0.3288(4) 0.5357(2) 0.0494(9) Uani d . . . 1 . .
S S6 -0.01928(11) 0.32721(8) 0.67066(5) 0.0390(2) Uani d . . . 1 . .
O O7 0.0447(4) 0.2211(2) 0.66149(18) 0.0532(7) Uani d . . . 1 . .
O O8 -0.1720(3) 0.3443(3) 0.71620(17) 0.0560(8) Uani d . . . 1 . .
C C9 0.1449(4) 0.4057(3) 0.7112(2) 0.0355(8) Uani d . . . 1 . .
C C10 0.1116(5) 0.4812(3) 0.7679(2) 0.0461(9) Uani d . . . 1 . .
H H10 0.0007 0.4908 0.7866 0.055 Uiso calc U . R 1 . .
C C11 0.2438(6) 0.5427(3) 0.7970(3) 0.0526(10) Uani d . . . 1 . .
H H11 0.2231 0.5941 0.8354 0.063 Uiso calc U . R 1 . .
C C12 0.4070(6) 0.5266(3) 0.7681(3) 0.0498(10) Uani d . . . 1 . .
C C13 0.4418(5) 0.4505(4) 0.7130(3) 0.0568(11) Uani d . . . 1 . .
H H14 0.5536 0.4395 0.6959 0.068 Uiso calc U . R 1 . .
C C14 0.3106(5) 0.3900(3) 0.6830(2) 0.0468(9) Uani d . . . 1 . .
H H15 0.3322 0.3392 0.6443 0.056 Uiso calc U . R 1 . .
Br Br15 0.59058(8) 0.61231(5) 0.80408(4) 0.0897(3) Uani d . . . 1 . .
C C16 0.0662(4) 0.5717(3) 0.5632(2) 0.0353(7) Uani d . . . 1 . .
C C17 0.1001(6) 0.6524(3) 0.6160(2) 0.0459(9) Uani d . . . 1 . .
H H17 0.026 0.6643 0.6583 0.055 Uiso calc U . R 1 . .
C C18 0.2440(7) 0.7163(4) 0.6067(3) 0.0578(12) Uani d . . . 1 . .
H H18 0.2664 0.7699 0.6431 0.069 Uiso calc U . R 1 . .
C C19 0.3529(6) 0.7001(4) 0.5436(3) 0.0593(12) Uani d . . . 1 . .
H H19 0.4494 0.7424 0.5374 0.071 Uiso calc U . R 1 . .
C C20 0.3185(6) 0.6213(4) 0.4902(3) 0.0556(11) Uani d . . . 1 . .
H H20 0.391 0.6112 0.447 0.067 Uiso calc U . R 1 . .
C C21 0.1766(5) 0.5563(3) 0.4997(2) 0.0462(9) Uani d . . . 1 . .
H H21 0.1556 0.5023 0.4633 0.055 Uiso calc U . R 1 . .
O O22 -0.2320(5) 0.2353(3) 0.5293(2) 0.0811(12) Uani d . . . 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
C1 C5 . 1.541(5) ?
C1 C2 . 1.550(5) ?
C1 S6 . 1.793(3) ?
C1 H1 . 0.98 ?
C2 C16 . 1.518(5) ?
C2 C3 . 1.552(5) ?
C2 H2 . 0.98 ?
C3 C4 . 1.532(6) ?
C3 H3A . 0.97 ?
C3 H3B . 0.97 ?
C4 C5 . 1.504(6) ?
C4 H4A . 0.97 ?
C4 H4B . 0.97 ?
C5 O22 . 1.196(5) ?
S6 O8 . 1.434(3) ?
S6 O7 . 1.439(3) ?
S6 C9 . 1.759(4) ?
C9 C10 . 1.374(5) ?
C9 C14 . 1.393(5) ?
C10 C11 . 1.382(6) ?
C10 H10 . 0.93 ?
C11 C12 . 1.380(6) ?
C11 H11 . 0.93 ?
C12 C13 . 1.362(6) ?
C12 Br15 . 1.896(4) ?
C13 C14 . 1.375(6) ?
C13 H14 . 0.93 ?
C14 H15 . 0.93 ?
C16 C17 . 1.377(5) ?
C16 C21 . 1.387(5) ?
C17 C18 . 1.393(6) ?
C17 H17 . 0.93 ?
C18 C19 . 1.375(7) ?
C18 H18 . 0.93 ?
C19 C20 . 1.368(6) ?
C19 H19 . 0.93 ?
C20 C21 . 1.389(6) ?
C20 H20 . 0.93 ?
C21 H21 . 0.93 ?

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
C5 C1 C2 . . 106.2(3) ?
C5 C1 S6 . . 109.6(2) ?
C2 C1 S6 . . 113.7(2) ?
C5 C1 H1 . . 109.1 ?
C2 C1 H1 . . 109.1 ?
S6 C1 H1 . . 109.1 ?
C16 C2 C1 . . 115.3(3) ?
C16 C2 C3 . . 113.2(3) ?
C1 C2 C3 . . 103.2(3) ?
C16 C2 H2 . . 108.3 ?
C1 C2 H2 . . 108.3 ?
C3 C2 H2 . . 108.3 ?
C4 C3 C2 . . 105.3(3) ?
C4 C3 H3A . . 110.7 ?
C2 C3 H3A . . 110.7 ?
C4 C3 H3B . . 110.7 ?
C2 C3 H3B . . 110.7 ?
H3A C3 H3B . . 108.8 ?
C5 C4 C3 . . 105.2(3) ?
C5 C4 H4A . . 110.7 ?
C3 C4 H4A . . 110.7 ?
C5 C4 H4B . . 110.7 ?
C3 C4 H4B . . 110.7 ?
H4A C4 H4B . . 108.8 ?
O22 C5 C4 . . 127.3(4) ?
O22 C5 C1 . . 124.2(4) ?
C4 C5 C1 . . 108.5(3) ?
O8 S6 O7 . . 119.12(18) ?
O8 S6 C9 . . 108.33(18) ?
O7 S6 C9 . . 108.30(17) ?
O8 S6 C1 . . 107.56(17) ?
O7 S6 C1 . . 108.08(17) ?
C9 S6 C1 . . 104.51(17) ?
C10 C9 C14 . . 120.7(4) ?
C10 C9 S6 . . 121.5(3) ?
C14 C9 S6 . . 117.7(3) ?
C9 C10 C11 . . 119.7(4) ?
C9 C10 H10 . . 120.2 ?
C11 C10 H10 . . 120.2 ?
C12 C11 C10 . . 118.9(4) ?
C12 C11 H11 . . 120.6 ?
C10 C11 H11 . . 120.6 ?
C13 C12 C11 . . 121.9(4) ?
C13 C12 Br15 . . 118.0(3) ?
C11 C12 Br15 . . 120.1(3) ?
C12 C13 C14 . . 119.6(4) ?
C12 C13 H14 . . 120.2 ?
C14 C13 H14 . . 120.2 ?
C13 C14 C9 . . 119.3(4) ?
C13 C14 H15 . . 120.4 ?
C9 C14 H15 . . 120.4 ?
C17 C16 C21 . . 118.7(4) ?
C17 C16 C2 . . 120.8(3) ?
C21 C16 C2 . . 120.4(3) ?
C16 C17 C18 . . 120.8(4) ?
C16 C17 H17 . . 119.6 ?
C18 C17 H17 . . 119.6 ?
C19 C18 C17 . . 120.0(4) ?
C19 C18 H18 . . 120.0 ?
C17 C18 H18 . . 120.0 ?
C20 C19 C18 . . 119.6(4) ?
C20 C19 H19 . . 120.2 ?
C18 C19 H19 . . 120.2 ?
C19 C20 C21 . . 120.8(4) ?
C19 C20 H20 . . 119.6 ?
C21 C20 H20 . . 119.6 ?
C16 C21 C20 . . 120.1(4) ?
C16 C21 H21 . . 120.0 ?
C20 C21 H21 . . 120.0 ?

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
C5 C1 C2 C16 . . . . -147.4(3) ?
S6 C1 C2 C16 . . . . 92.1(3) ?
C5 C1 C2 C3 . . . . -23.5(4) ?
S6 C1 C2 C3 . . . . -144.0(3) ?
C16 C2 C3 C4 . . . . 159.3(3) ?
C1 C2 C3 C4 . . . . 34.1(4) ?
C2 C3 C4 C5 . . . . -31.7(4) ?
C3 C4 C5 O22 . . . . -161.9(5) ?
C3 C4 C5 C1 . . . . 16.7(5) ?
C2 C1 C5 O22 . . . . -176.7(4) ?
S6 C1 C5 O22 . . . . -53.6(5) ?
C2 C1 C5 C4 . . . . 4.6(4) ?
S6 C1 C5 C4 . . . . 127.7(3) ?
C5 C1 S6 O8 . . . . -57.3(3) ?
C2 C1 S6 O8 . . . . 61.3(3) ?
C5 C1 S6 O7 . . . . 72.5(3) ?
C2 C1 S6 O7 . . . . -168.9(2) ?
C5 C1 S6 C9 . . . . -172.3(3) ?
C2 C1 S6 C9 . . . . -53.7(3) ?
O8 S6 C9 C10 . . . . -9.8(4) ?
O7 S6 C9 C10 . . . . -140.3(3) ?
C1 S6 C9 C10 . . . . 104.6(3) ?
O8 S6 C9 C14 . . . . 171.1(3) ?
O7 S6 C9 C14 . . . . 40.6(4) ?
C1 S6 C9 C14 . . . . -74.4(3) ?
C14 C9 C10 C11 . . . . 0.4(6) ?
S6 C9 C10 C11 . . . . -178.6(3) ?
C9 C10 C11 C12 . . . . 0.0(6) ?
C10 C11 C12 C13 . . . . -1.4(6) ?
C10 C11 C12 Br15 . . . . 178.1(3) ?
C11 C12 C13 C14 . . . . 2.3(7) ?
Br15 C12 C13 C14 . . . . -177.2(3) ?
C12 C13 C14 C9 . . . . -1.9(7) ?
C10 C9 C14 C13 . . . . 0.5(6) ?
S6 C9 C14 C13 . . . . 179.6(3) ?
C1 C2 C16 C17 . . . . -127.7(4) ?
C3 C2 C16 C17 . . . . 113.8(4) ?
C1 C2 C16 C21 . . . . 53.2(5) ?
C3 C2 C16 C21 . . . . -65.2(4) ?
C21 C16 C17 C18 . . . . -1.1(6) ?
C2 C16 C17 C18 . . . . 179.8(4) ?
C16 C17 C18 C19 . . . . 0.9(7) ?
C17 C18 C19 C20 . . . . 0.3(7) ?
C18 C19 C20 C21 . . . . -1.2(7) ?
C17 C16 C21 C20 . . . . 0.2(6) ?
C2 C16 C21 C20 . . . . 179.3(4) ?
C19 C20 C21 C16 . . . . 1.0(7) ?

####################################################################### 
# 
# 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_2S_3S-14i
_database_code_depnum_ccdc_archive 'CCDC 1529449'
_audit_update_record             
;
2017-01-24 deposited with the CCDC.
2017-02-28 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C17 H15 Br O3 S'
_chemical_formula_sum            'C17 H15 Br O3 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         379.26
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   7.8064(14)
_cell_length_b                   12.6377(19)
_cell_length_c                   16.783(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1655.7(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2480
_cell_measurement_theta_min      2.8778
_cell_measurement_theta_max      21.9468
_cell_measurement_temperature    292.(2)

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.220
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768

_exptl_absorpt_coefficient_mu    2.617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.6412
_exptl_absorpt_correction_T_max  0.7455

_exptl_special_details           
;
;

_diffrn_ambient_temperature      292.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              Bruker

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEX II DUO'
_diffrn_measurement_method       'φ & ω  scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            10139
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0702
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         27.13
_diffrn_reflns_theta_full        27.13
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21

_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.
;

_reflns_number_total             3622
_reflns_number_gt                2782
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0895
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_number_reflns         3622
_refine_ls_number_parameters     199
_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)+0.2765P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.497
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 938 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.025(6)

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'

_computing_data_collection       'Bruker Instrument Service v2010, 1, 0, 0'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_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
C C1 0.4456(5) 0.3810(3) 0.9265(2) 0.0375(9) Uani d . . . 1 . .
H H1 0.5458 0.3665 0.9599 0.045 Uiso calc U . R 1 . .
C C2 0.4092(5) 0.5017(3) 0.9264(2) 0.0364(9) Uani d . . . 1 . .
H H2 0.3538 0.5202 0.8759 0.044 Uiso calc U . R 1 . .
C C3 0.2765(6) 0.5152(4) 0.9944(3) 0.0522(12) Uani d . . . 1 . .
H H3A 0.3336 0.5221 1.0455 0.063 Uiso calc U . R 1 . .
H H3B 0.2062 0.5773 0.9855 0.063 Uiso calc U . R 1 . .
C C4 0.1673(6) 0.4143(4) 0.9919(3) 0.0529(12) Uani d . . . 1 . .
H H4A 0.1224 0.3979 1.0443 0.064 Uiso calc U . R 1 . .
H H4B 0.0722 0.4226 0.9552 0.064 Uiso calc U . R 1 . .
C C5 0.2867(6) 0.3288(4) 0.9639(3) 0.0487(11) Uani d . . . 1 . .
S S6 0.48050(12) 0.32722(8) 0.82934(6) 0.0392(3) Uani d . . . 1 . .
O O7 0.5445(4) 0.2212(2) 0.8385(2) 0.0541(8) Uani d . . . 1 . .
O O8 0.3282(4) 0.3443(3) 0.78378(19) 0.0565(9) Uani d . . . 1 . .
C C9 0.6449(5) 0.4054(3) 0.7891(2) 0.0360(9) Uani d . . . 1 . .
C C10 0.8105(5) 0.3900(3) 0.8168(3) 0.0465(10) Uani d . . . 1 . .
H H10 0.8324 0.3391 0.8556 0.056 Uiso calc U . R 1 . .
C C11 0.9417(6) 0.4503(4) 0.7867(3) 0.0578(13) Uani d . . . 1 . .
H H11 1.0536 0.439 0.8037 0.069 Uiso calc U . R 1 . .
C C12 0.9066(6) 0.5266(3) 0.7320(3) 0.0495(11) Uani d . . . 1 . .
C C13 0.7430(6) 0.5421(4) 0.7030(3) 0.0523(12) Uani d . . . 1 . .
H H13 0.7222 0.5932 0.6643 0.063 Uiso calc U . R 1 . .
C C14 0.6120(6) 0.4814(4) 0.7320(3) 0.0453(11) Uani d . . . 1 . .
H H14 0.501 0.4913 0.7133 0.054 Uiso calc U . R 1 . .
Br Br15 1.09059(9) 0.61228(5) 0.69591(4) 0.0900(3) Uani d . . . 1 . .
C C16 0.5663(5) 0.5712(3) 0.9366(2) 0.0352(9) Uani d . . . 1 . .
C C17 0.6001(6) 0.6519(3) 0.8840(2) 0.0443(10) Uani d . . . 1 . .
H H17 0.526 0.6638 0.8415 0.053 Uiso calc U . R 1 . .
C C18 0.7439(7) 0.7163(4) 0.8933(3) 0.0577(13) Uani d . . . 1 . .
H H18 0.7662 0.7699 0.8568 0.069 Uiso calc U . R 1 . .
C C19 0.8524(7) 0.7001(4) 0.9567(3) 0.0593(14) Uani d . . . 1 . .
H H19 0.9485 0.7427 0.9632 0.071 Uiso calc U . R 1 . .
C C20 0.8182(6) 0.6210(4) 1.0102(3) 0.0544(12) Uani d . . . 1 . .
H H20 0.8908 0.6106 1.0534 0.065 Uiso calc U . R 1 . .
C C21 0.6766(6) 0.5563(4) 1.0004(3) 0.0461(11) Uani d . . . 1 . .
H H21 0.6553 0.5025 1.0369 0.055 Uiso calc U . R 1 . .
O O22 0.2671(6) 0.2353(3) 0.9707(3) 0.0811(13) Uani d . . . 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
C1 C5 . 1.538(6) ?
C1 C2 . 1.552(5) ?
C1 S6 . 1.787(4) ?
C1 H1 . 0.98 ?
C2 C16 . 1.518(5) ?
C2 C3 . 1.550(6) ?
C2 H2 . 0.98 ?
C3 C4 . 1.534(7) ?
C3 H3A . 0.97 ?
C3 H3B . 0.97 ?
C4 C5 . 1.503(7) ?
C4 H4A . 0.97 ?
C4 H4B . 0.97 ?
C5 O22 . 1.197(5) ?
S6 O8 . 1.430(3) ?
S6 O7 . 1.438(3) ?
S6 C9 . 1.755(4) ?
C9 C14 . 1.382(6) ?
C9 C10 . 1.388(6) ?
C10 C11 . 1.373(6) ?
C10 H10 . 0.93 ?
C11 C12 . 1.360(7) ?
C11 H11 . 0.93 ?
C12 C13 . 1.381(7) ?
C12 Br15 . 1.898(4) ?
C13 C14 . 1.368(6) ?
C13 H13 . 0.93 ?
C14 H14 . 0.93 ?
C16 C17 . 1.375(6) ?
C16 C21 . 1.387(6) ?
C17 C18 . 1.394(7) ?
C17 H17 . 0.93 ?
C18 C19 . 1.374(7) ?
C18 H18 . 0.93 ?
C19 C20 . 1.370(7) ?
C19 H19 . 0.93 ?
C20 C21 . 1.385(6) ?
C20 H20 . 0.93 ?
C21 H21 . 0.93 ?

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
C5 C1 C2 . . 105.9(3) ?
C5 C1 S6 . . 109.4(3) ?
C2 C1 S6 . . 113.6(3) ?
C5 C1 H1 . . 109.3 ?
C2 C1 H1 . . 109.3 ?
S6 C1 H1 . . 109.3 ?
C16 C2 C3 . . 113.2(3) ?
C16 C2 C1 . . 114.9(3) ?
C3 C2 C1 . . 103.3(3) ?
C16 C2 H2 . . 108.4 ?
C3 C2 H2 . . 108.4 ?
C1 C2 H2 . . 108.4 ?
C4 C3 C2 . . 105.1(4) ?
C4 C3 H3A . . 110.7 ?
C2 C3 H3A . . 110.7 ?
C4 C3 H3B . . 110.7 ?
C2 C3 H3B . . 110.7 ?
H3A C3 H3B . . 108.8 ?
C5 C4 C3 . . 105.1(4) ?
C5 C4 H4A . . 110.7 ?
C3 C4 H4A . . 110.7 ?
C5 C4 H4B . . 110.7 ?
C3 C4 H4B . . 110.7 ?
H4A C4 H4B . . 108.8 ?
O22 C5 C4 . . 126.9(4) ?
O22 C5 C1 . . 124.4(4) ?
C4 C5 C1 . . 108.6(4) ?
O8 S6 O7 . . 119.1(2) ?
O8 S6 C9 . . 108.51(19) ?
O7 S6 C9 . . 108.14(19) ?
O8 S6 C1 . . 107.68(18) ?
O7 S6 C1 . . 108.04(19) ?
C9 S6 C1 . . 104.40(19) ?
C14 C9 C10 . . 120.2(4) ?
C14 C9 S6 . . 121.5(3) ?
C10 C9 S6 . . 118.2(3) ?
C11 C10 C9 . . 119.6(4) ?
C11 C10 H10 . . 120.2 ?
C9 C10 H10 . . 120.2 ?
C12 C11 C10 . . 119.5(4) ?
C12 C11 H11 . . 120.3 ?
C10 C11 H11 . . 120.3 ?
C11 C12 C13 . . 121.7(4) ?
C11 C12 Br15 . . 117.9(4) ?
C13 C12 Br15 . . 120.4(3) ?
C14 C13 C12 . . 119.1(4) ?
C14 C13 H13 . . 120.4 ?
C12 C13 H13 . . 120.4 ?
C13 C14 C9 . . 119.9(4) ?
C13 C14 H14 . . 120.1 ?
C9 C14 H14 . . 120.1 ?
C17 C16 C21 . . 118.5(4) ?
C17 C16 C2 . . 120.8(4) ?
C21 C16 C2 . . 120.7(4) ?
C16 C17 C18 . . 121.0(4) ?
C16 C17 H17 . . 119.5 ?
C18 C17 H17 . . 119.5 ?
C19 C18 C17 . . 119.8(5) ?
C19 C18 H18 . . 120.1 ?
C17 C18 H18 . . 120.1 ?
C20 C19 C18 . . 119.7(5) ?
C20 C19 H19 . . 120.2 ?
C18 C19 H19 . . 120.2 ?
C19 C20 C21 . . 120.6(5) ?
C19 C20 H20 . . 119.7 ?
C21 C20 H20 . . 119.7 ?
C20 C21 C16 . . 120.5(4) ?
C20 C21 H21 . . 119.8 ?
C16 C21 H21 . . 119.8 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 C1 C2 C16 . . . . 147.7(3) ?
S6 C1 C2 C16 . . . . -92.1(4) ?
C5 C1 C2 C3 . . . . 24.1(4) ?
S6 C1 C2 C3 . . . . 144.2(3) ?
C16 C2 C3 C4 . . . . -159.3(4) ?
C1 C2 C3 C4 . . . . -34.5(4) ?
C2 C3 C4 C5 . . . . 31.9(5) ?
C3 C4 C5 O22 . . . . 161.5(5) ?
C3 C4 C5 C1 . . . . -16.7(5) ?
C2 C1 C5 O22 . . . . 176.9(5) ?
S6 C1 C5 O22 . . . . 54.1(6) ?
C2 C1 C5 C4 . . . . -4.9(5) ?
S6 C1 C5 C4 . . . . -127.7(3) ?
C5 C1 S6 O8 . . . . 57.1(3) ?
C2 C1 S6 O8 . . . . -61.1(3) ?
C5 C1 S6 O7 . . . . -72.8(3) ?
C2 C1 S6 O7 . . . . 169.1(3) ?
C5 C1 S6 C9 . . . . 172.3(3) ?
C2 C1 S6 C9 . . . . 54.2(3) ?
O8 S6 C9 C14 . . . . 9.9(4) ?
O7 S6 C9 C14 . . . . 140.4(3) ?
C1 S6 C9 C14 . . . . -104.8(4) ?
O8 S6 C9 C10 . . . . -170.9(3) ?
O7 S6 C9 C10 . . . . -40.4(4) ?
C1 S6 C9 C10 . . . . 74.5(4) ?
C14 C9 C10 C11 . . . . -0.5(7) ?
S6 C9 C10 C11 . . . . -179.7(4) ?
C9 C10 C11 C12 . . . . 2.1(7) ?
C10 C11 C12 C13 . . . . -2.9(7) ?
C10 C11 C12 Br15 . . . . 177.1(4) ?
C11 C12 C13 C14 . . . . 2.1(7) ?
Br15 C12 C13 C14 . . . . -177.9(3) ?
C12 C13 C14 C9 . . . . -0.4(7) ?
C10 C9 C14 C13 . . . . -0.4(6) ?
S6 C9 C14 C13 . . . . 178.8(3) ?
C3 C2 C16 C17 . . . . -113.7(4) ?
C1 C2 C16 C17 . . . . 128.0(4) ?
C3 C2 C16 C21 . . . . 64.6(5) ?
C1 C2 C16 C21 . . . . -53.7(5) ?
C21 C16 C17 C18 . . . . 1.3(6) ?
C2 C16 C17 C18 . . . . 179.7(4) ?
C16 C17 C18 C19 . . . . -1.0(7) ?
C17 C18 C19 C20 . . . . -0.1(8) ?
C18 C19 C20 C21 . . . . 0.8(8) ?
C19 C20 C21 C16 . . . . -0.5(7) ?
C17 C16 C21 C20 . . . . -0.6(6) ?
C2 C16 C21 C20 . . . . -179.0(4) ?

