# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_ta_a
_database_code_depnum_ccdc_archive 'CCDC 1899806'
loop_
_audit_author_name
_audit_author_address
xie-yy
;Shanghai jiaotong university
China
;
_audit_update_record             
;
2019-02-27 deposited with the CCDC.	2019-07-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H13 Br O2 S'
_chemical_formula_sum            'C16 H13 Br O2 S'
_chemical_formula_weight         349.23

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'
Br Br -0.6763 1.2805 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   5.29670(10)
_cell_length_b                   10.3438(2)
_cell_length_c                   28.0395(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1536.23(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    9978
_cell_measurement_theta_min      3.15
_cell_measurement_theta_max      68.11

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   0.5074
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    4.902
_shelx_estimated_absorpt_T_min   0.412
_shelx_estimated_absorpt_T_max   0.441
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20349
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.152
_diffrn_reflns_theta_max         68.384
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2814
_reflns_number_gt                2568
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.998

_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.1155P)²+1.3770P] 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_abs_structure_details 
;
 Flack x determined using 951 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.039(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2814
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0685
_refine_ls_wR_factor_ref         0.2062
_refine_ls_wR_factor_gt          0.2008
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.9381(5) -0.0213(2) 0.75566(7) 0.2071(14) Uani 1 1 d . . . . .
C1 C 0.833(2) 0.0969(13) 0.7079(4) 0.102(4) Uani 1 1 d . . . . .
O1 O 0.4179(8) 0.3122(5) 0.57077(16) 0.0577(11) Uani 1 1 d . . . . .
S1 S 1.0051(3) 0.54845(16) 0.59483(8) 0.0688(5) Uani 1 1 d . . . . .
O2 O 0.2872(9) 0.3388(5) 0.49647(18) 0.0688(13) Uani 1 1 d . . . . .
C2 C 0.657(6) 0.1814(19) 0.7169(4) 0.184(10) Uani 1 1 d . . . . .
H2 H 0.584538 0.183884 0.747010 0.221 Uiso 1 1 calc R U . . .
C5 C 0.860(3) 0.1848(16) 0.6320(5) 0.171(9) Uani 1 1 d . . . . .
H5 H 0.936186 0.181270 0.602165 0.205 Uiso 1 1 calc R U . . .
C4 C 0.6855(13) 0.2738(7) 0.6394(2) 0.0578(15) Uani 1 1 d . . . . .
C3 C 0.578(4) 0.2669(15) 0.6825(4) 0.153(7) Uani 1 1 d . . . . .
H3 H 0.443987 0.322014 0.689503 0.183 Uiso 1 1 calc R U . . .
C6 C 0.934(4) 0.098(2) 0.6658(6) 0.208(12) Uani 1 1 d . . . . .
H6 H 1.058829 0.037767 0.658444 0.250 Uiso 1 1 calc R U . . .
C7 C 0.6029(12) 0.3714(6) 0.6033(2) 0.0557(14) Uani 1 1 d . . . . .
H7 H 0.523569 0.444489 0.619797 0.067 Uiso 1 1 calc R U . . .
C9 C 0.6559(13) 0.4548(7) 0.5250(3) 0.0629(16) Uani 1 1 d . . . . .
H9A H 0.599991 0.544112 0.525626 0.076 Uiso 1 1 calc R U . . .
H9B H 0.755871 0.440688 0.496519 0.076 Uiso 1 1 calc R U . . .
C8 C 0.8053(12) 0.4228(6) 0.5691(2) 0.0554(14) Uani 1 1 d . . . . .
H8 H 0.915445 0.349853 0.561028 0.066 Uiso 1 1 calc R U . . .
C10 C 0.4364(11) 0.3646(6) 0.5267(2) 0.0557(14) Uani 1 1 d . . . . .
C11 C 0.7986(13) 0.6829(6) 0.5984(3) 0.0624(16) Uani 1 1 d . . . . .
C12 C 0.7929(18) 0.7710(8) 0.5612(4) 0.080(2) Uani 1 1 d . . . . .
H12 H 0.895916 0.758278 0.534745 0.097 Uiso 1 1 calc R U . . .
C13 C 0.636(2) 0.8779(10) 0.5629(5) 0.105(3) Uani 1 1 d . . . . .
H13 H 0.634712 0.938071 0.538241 0.126 Uiso 1 1 calc R U . . .
C14 C 0.482(3) 0.8929(12) 0.6015(6) 0.138(5) Uani 1 1 d . . . . .
H14 H 0.374345 0.963808 0.602269 0.166 Uiso 1 1 calc R U . . .
C15 C 0.479(3) 0.8109(13) 0.6383(5) 0.136(5) Uani 1 1 d . . . . .
H15 H 0.370234 0.824101 0.663913 0.163 Uiso 1 1 calc R U . . .
C16 C 0.647(2) 0.7019(9) 0.6374(3) 0.090(3) Uani 1 1 d . . . . .
H16 H 0.652837 0.644770 0.662965 0.108 Uiso 1 1 calc R U . . .


_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 C1 1.896(10) . ?
C1 C6 1.295(19) . ?
C1 C2 1.30(2) . ?
O1 C10 1.353(8) . ?
O1 C7 1.473(8) . ?
S1 C11 1.772(7) . ?
S1 C8 1.825(6) . ?
O2 C10 1.189(8) . ?
C2 C3 1.37(2) . ?
C2 H2 0.9300 . ?
C5 C4 1.320(14) . ?
C5 C6 1.365(16) . ?
C5 H5 0.9300 . ?
C4 C3 1.339(12) . ?
C4 C7 1.496(10) . ?
C3 H3 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.534(9) . ?
C7 H7 0.9800 . ?
C9 C10 1.492(9) . ?
C9 C8 1.503(9) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C8 H8 0.9800 . ?
C11 C16 1.371(12) . ?
C11 C12 1.385(11) . ?
C12 C13 1.385(13) . ?
C12 H12 0.9300 . ?
C13 C14 1.362(19) . ?
C13 H13 0.9300 . ?
C14 C15 1.336(19) . ?
C14 H14 0.9300 . ?
C15 C16 1.438(17) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?

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 117.7(11) . . ?
C6 C1 Br1 121.9(12) . . ?
C2 C1 Br1 120.4(10) . . ?
C10 O1 C7 110.6(5) . . ?
C11 S1 C8 102.9(3) . . ?
C1 C2 C3 121.2(12) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C4 C5 C6 123.5(11) . . ?
C4 C5 H5 118.3 . . ?
C6 C5 H5 118.3 . . ?
C5 C4 C3 113.8(10) . . ?
C5 C4 C7 124.7(7) . . ?
C3 C4 C7 121.5(9) . . ?
C4 C3 C2 122.4(15) . . ?
C4 C3 H3 118.8 . . ?
C2 C3 H3 118.8 . . ?
C1 C6 C5 121.3(14) . . ?
C1 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
O1 C7 C4 109.5(5) . . ?
O1 C7 C8 102.7(5) . . ?
C4 C7 C8 116.9(5) . . ?
O1 C7 H7 109.1 . . ?
C4 C7 H7 109.1 . . ?
C8 C7 H7 109.1 . . ?
C10 C9 C8 104.3(6) . . ?
C10 C9 H9A 110.9 . . ?
C8 C9 H9A 110.9 . . ?
C10 C9 H9B 110.9 . . ?
C8 C9 H9B 110.9 . . ?
H9A C9 H9B 108.9 . . ?
C9 C8 C7 102.9(5) . . ?
C9 C8 S1 118.2(5) . . ?
C7 C8 S1 113.8(5) . . ?
C9 C8 H8 107.1 . . ?
C7 C8 H8 107.1 . . ?
S1 C8 H8 107.1 . . ?
O2 C10 O1 120.9(6) . . ?
O2 C10 C9 129.5(6) . . ?
O1 C10 C9 109.6(5) . . ?
C16 C11 C12 119.5(7) . . ?
C16 C11 S1 121.2(6) . . ?
C12 C11 S1 119.2(6) . . ?
C13 C12 C11 120.8(9) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C14 C13 C12 118.5(10) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
C15 C14 C13 123.4(11) . . ?
C15 C14 H14 118.3 . . ?
C13 C14 H14 118.3 . . ?
C14 C15 C16 118.4(12) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
C11 C16 C15 119.3(10) . . ?
C11 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?

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(3) . . . . ?
Br1 C1 C2 C3 -179.4(16) . . . . ?
C6 C5 C4 C3 -3(3) . . . . ?
C6 C5 C4 C7 179.2(18) . . . . ?
C5 C4 C3 C2 5(3) . . . . ?
C7 C4 C3 C2 -177.4(16) . . . . ?
C1 C2 C3 C4 -4(3) . . . . ?
C2 C1 C6 C5 1(3) . . . . ?
Br1 C1 C6 C5 -178.8(17) . . . . ?
C4 C5 C6 C1 1(4) . . . . ?
C10 O1 C7 C4 -148.2(5) . . . . ?
C10 O1 C7 C8 -23.3(6) . . . . ?
C5 C4 C7 O1 81.7(14) . . . . ?
C3 C4 C7 O1 -95.7(12) . . . . ?
C5 C4 C7 C8 -34.6(15) . . . . ?
C3 C4 C7 C8 148.1(12) . . . . ?
C10 C9 C8 C7 -27.8(7) . . . . ?
C10 C9 C8 S1 -154.2(5) . . . . ?
O1 C7 C8 C9 30.8(6) . . . . ?
C4 C7 C8 C9 150.7(6) . . . . ?
O1 C7 C8 S1 160.0(4) . . . . ?
C4 C7 C8 S1 -80.2(6) . . . . ?
C11 S1 C8 C9 49.5(6) . . . . ?
C11 S1 C8 C7 -71.4(5) . . . . ?
C7 O1 C10 O2 -172.7(6) . . . . ?
C7 O1 C10 C9 5.8(7) . . . . ?
C8 C9 C10 O2 -167.0(7) . . . . ?
C8 C9 C10 O1 14.7(7) . . . . ?
C8 S1 C11 C16 87.4(8) . . . . ?
C8 S1 C11 C12 -93.3(6) . . . . ?
C16 C11 C12 C13 -0.1(14) . . . . ?
S1 C11 C12 C13 -179.4(9) . . . . ?
C11 C12 C13 C14 -1.5(19) . . . . ?
C12 C13 C14 C15 1(3) . . . . ?
C13 C14 C15 C16 1(3) . . . . ?
C12 C11 C16 C15 1.9(16) . . . . ?
S1 C11 C16 C15 -178.8(10) . . . . ?
C14 C15 C16 C11 -2(2) . . . . ?

_refine_diff_density_max         0.972
_refine_diff_density_min         -1.053
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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_a_a
_database_code_depnum_ccdc_archive 'CCDC 1938651'
loop_
_audit_author_name
_audit_author_address
'Yu-Yang Xie'
;Shanghai jiaotong university
China
;
_audit_update_record             
;
2019-07-05 deposited with the CCDC.	2019-07-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 O2 S'
_chemical_formula_sum            'C18 H18 O2 S'
_chemical_formula_weight         298.38

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_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'

_cell_length_a                   6.790(3)
_cell_length_b                   8.390(2)
_cell_length_c                   8.689(3)
_cell_angle_alpha                108.45(3)
_cell_angle_beta                 102.39(3)
_cell_angle_gamma                112.79(4)
_cell_volume                     399.4(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4783
_cell_measurement_theta_min      5.81
_cell_measurement_theta_max      68.23

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_F_000             158
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.805
_shelx_estimated_absorpt_T_min   0.737
_shelx_estimated_absorpt_T_max   0.774
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7576
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         6.385
_diffrn_reflns_theta_max         68.652
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             2841
_reflns_number_gt                2595
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.930
_reflns_Friedel_fraction_max     0.925
_reflns_Friedel_fraction_full    0.935

_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0436P)²+0.0257P] 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_abs_structure_details 
;
 Flack x determined using 1101 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.081(12)
_chemical_absolute_configuration AD
_refine_ls_number_reflns         2841
_refine_ls_number_parameters     190
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.0982
_refine_ls_wR_factor_gt          0.0932
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.50736(12) 0.32225(11) 0.60491(10) 0.0670(3) Uani 1 1 d . . . . .
C1 C 0.7954(6) 0.4571(5) 0.7617(4) 0.0568(8) Uani 1 1 d . . . . .
O1 O 0.1251(4) 0.2099(4) 0.2862(3) 0.0729(7) Uani 1 1 d . . . . .
C3 C 1.0477(9) 0.6336(9) 1.0664(6) 0.1058(18) Uani 1 1 d . . . . .
H3 H 1.066671 0.682627 1.183915 0.127 Uiso 1 1 calc R U . . .
O2 O -0.2303(6) 0.1467(7) 0.1994(6) 0.1197(13) Uani 1 1 d . . . . .
C2 C 0.8289(9) 0.5348(8) 0.9370(6) 0.0911(14) Uani 1 1 d . . . . .
H2 H 0.702400 0.520310 0.968089 0.109 Uiso 1 1 calc R U . . .
C5 C 1.2047(7) 0.5865(8) 0.8530(6) 0.0881(13) Uani 1 1 d . . . . .
H5 H 1.332720 0.605338 0.823049 0.106 Uiso 1 1 calc R U . . .
C4 C 1.2352(8) 0.6603(7) 1.0252(6) 0.0869(13) Uani 1 1 d . . . . .
H4 H 1.382625 0.727990 1.113161 0.104 Uiso 1 1 calc R U . . .
C6 C 0.9857(7) 0.4836(7) 0.7216(5) 0.0780(11) Uani 1 1 d . . . . .
H6 H 0.967928 0.431880 0.604517 0.094 Uiso 1 1 calc R U . . .
C7 C 0.5943(6) 0.5671(5) 0.4448(4) 0.0598(8) Uani 1 1 d . . . . .
C9 C 0.8340(10) 0.8620(8) 0.4386(7) 0.1049(18) Uani 1 1 d . . . . .
H9 H 0.962306 0.935814 0.421008 0.126 Uiso 1 1 calc R U . . .
C8 C 0.7828(8) 0.6773(7) 0.4185(6) 0.0822(12) Uani 1 1 d . . . . .
H8 H 0.877086 0.628011 0.386875 0.099 Uiso 1 1 calc R U . . .
C10 C 0.6964(12) 0.9341(7) 0.4839(7) 0.1026(17) Uani 1 1 d . . . . .
H10 H 0.728979 1.056437 0.494815 0.123 Uiso 1 1 calc R U . . .
C11 C 0.5133(11) 0.8302(8) 0.5132(6) 0.0918(14) Uani 1 1 d . . . . .
H11 H 0.422154 0.882353 0.546593 0.110 Uiso 1 1 calc R U . . .
C12 C 0.4590(7) 0.6456(6) 0.4941(5) 0.0727(10) Uani 1 1 d . . . . .
H12 H 0.331788 0.574750 0.514374 0.087 Uiso 1 1 calc R U . . .
C13 C 0.5377(6) 0.3659(5) 0.4160(4) 0.0588(8) Uani 1 1 d . . . . .
H13 H 0.669257 0.350838 0.400307 0.071 Uiso 1 1 calc R U . . .
C14 C 0.3243(7) 0.2079(6) 0.2523(5) 0.0648(9) Uani 1 1 d . . . . .
H14 H 0.313819 0.083772 0.237440 0.078 Uiso 1 1 calc R U . . .
C15 C 0.3281(7) 0.2267(7) 0.0859(5) 0.0828(12) Uani 1 1 d . . . . .
H15A H 0.456752 0.215899 0.062164 0.099 Uiso 1 1 calc R U . . .
H15B H 0.348385 0.352052 0.099650 0.099 Uiso 1 1 calc R U . . .
C16 C 0.1020(9) 0.0688(9) -0.0662(6) 0.0997(16) Uani 1 1 d . . . . .
H16A H 0.100965 0.083449 -0.172713 0.120 Uiso 1 1 calc R U . . .
H16B H 0.087215 -0.056390 -0.085393 0.120 Uiso 1 1 calc R U . . .
C17 C -0.0940(10) 0.0804(12) -0.0264(7) 0.128(2) Uani 1 1 d . . . . .
H17A H -0.230052 -0.046247 -0.095690 0.153 Uiso 1 1 calc R U . . .
H17B H -0.122681 0.167475 -0.067080 0.153 Uiso 1 1 calc R U . . .
C18 C -0.0729(7) 0.1443(7) 0.1588(6) 0.0801(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.768(4) . ?
S1 C13 1.827(3) . ?
C1 C6 1.364(5) . ?
C1 C2 1.380(6) . ?
O1 C18 1.318(5) . ?
O1 C14 1.450(5) . ?
C3 C4 1.351(7) . ?
C3 C2 1.378(7) . ?
C3 H3 0.9300 . ?
O2 C18 1.201(6) . ?
C2 H2 0.9300 . ?
C5 C4 1.359(7) . ?
C5 C6 1.383(6) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.374(6) . ?
C7 C12 1.386(6) . ?
C7 C13 1.500(5) . ?
C9 C10 1.356(9) . ?
C9 C8 1.392(7) . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?
C10 C11 1.344(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.389(7) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.521(5) . ?
C13 H13 0.9800 . ?
C14 C15 1.507(6) . ?
C14 H14 0.9800 . ?
C15 C16 1.518(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.475(8) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.481(8) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?

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 C13 103.01(17) . . ?
C6 C1 C2 117.8(4) . . ?
C6 C1 S1 124.5(3) . . ?
C2 C1 S1 117.6(3) . . ?
C18 O1 C14 122.4(3) . . ?
C4 C3 C2 121.0(4) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C2 C1 120.7(4) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C5 C6 120.9(4) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C3 C4 C5 118.8(4) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C1 C6 C5 120.8(4) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C8 C7 C12 118.3(4) . . ?
C8 C7 C13 119.7(4) . . ?
C12 C7 C13 122.0(3) . . ?
C10 C9 C8 119.9(5) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C7 C8 C9 120.6(5) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C11 C10 C9 120.5(5) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 120.6(5) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C7 C12 C11 120.1(5) . . ?
C7 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C7 C13 C14 114.5(3) . . ?
C7 C13 S1 113.0(2) . . ?
C14 C13 S1 108.7(2) . . ?
C7 C13 H13 106.7 . . ?
C14 C13 H13 106.7 . . ?
S1 C13 H13 106.7 . . ?
O1 C14 C15 111.6(3) . . ?
O1 C14 C13 107.0(3) . . ?
C15 C14 C13 114.1(3) . . ?
O1 C14 H14 108.0 . . ?
C15 C14 H14 108.0 . . ?
C13 C14 H14 108.0 . . ?
C14 C15 C16 109.4(4) . . ?
C14 C15 H15A 109.8 . . ?
C16 C15 H15A 109.8 . . ?
C14 C15 H15B 109.8 . . ?
C16 C15 H15B 109.8 . . ?
H15A C15 H15B 108.2 . . ?
C17 C16 C15 109.7(4) . . ?
C17 C16 H16A 109.7 . . ?
C15 C16 H16A 109.7 . . ?
C17 C16 H16B 109.7 . . ?
C15 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
C16 C17 C18 118.1(4) . . ?
C16 C17 H17A 107.8 . . ?
C18 C17 H17A 107.8 . . ?
C16 C17 H17B 107.8 . . ?
C18 C17 H17B 107.8 . . ?
H17A C17 H17B 107.1 . . ?
O2 C18 O1 117.7(4) . . ?
O2 C18 C17 121.7(4) . . ?
O1 C18 C17 120.5(4) . . ?

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
C13 S1 C1 C6 -33.8(4) . . . . ?
C13 S1 C1 C2 148.8(4) . . . . ?
C4 C3 C2 C1 1.3(9) . . . . ?
C6 C1 C2 C3 -0.8(8) . . . . ?
S1 C1 C2 C3 176.9(5) . . . . ?
C2 C3 C4 C5 -0.5(9) . . . . ?
C6 C5 C4 C3 -0.8(9) . . . . ?
C2 C1 C6 C5 -0.5(7) . . . . ?
S1 C1 C6 C5 -178.0(4) . . . . ?
C4 C5 C6 C1 1.3(8) . . . . ?
C12 C7 C8 C9 -0.9(6) . . . . ?
C13 C7 C8 C9 177.8(4) . . . . ?
C10 C9 C8 C7 -0.3(7) . . . . ?
C8 C9 C10 C11 1.4(8) . . . . ?
C9 C10 C11 C12 -1.3(7) . . . . ?
C8 C7 C12 C11 0.9(6) . . . . ?
C13 C7 C12 C11 -177.7(3) . . . . ?
C10 C11 C12 C7 0.1(6) . . . . ?
C8 C7 C13 C14 -108.0(4) . . . . ?
C12 C7 C13 C14 70.6(4) . . . . ?
C8 C7 C13 S1 126.9(3) . . . . ?
C12 C7 C13 S1 -54.5(4) . . . . ?
C1 S1 C13 C7 -71.6(3) . . . . ?
C1 S1 C13 C14 160.3(2) . . . . ?
C18 O1 C14 C15 30.1(5) . . . . ?
C18 O1 C14 C13 155.5(4) . . . . ?
C7 C13 C14 O1 -71.0(4) . . . . ?
S1 C13 C14 O1 56.4(3) . . . . ?
C7 C13 C14 C15 52.9(4) . . . . ?
S1 C13 C14 C15 -179.7(3) . . . . ?
O1 C14 C15 C16 -55.5(5) . . . . ?
C13 C14 C15 C16 -176.9(3) . . . . ?
C14 C15 C16 C17 57.0(6) . . . . ?
C15 C16 C17 C18 -33.8(9) . . . . ?
C14 O1 C18 O2 177.9(4) . . . . ?
C14 O1 C18 C17 -5.4(7) . . . . ?
C16 C17 C18 O2 -175.7(6) . . . . ?
C16 C17 C18 O1 7.7(10) . . . . ?

_refine_diff_density_max         0.156
_refine_diff_density_min         -0.110
_refine_diff_density_rms         0.026

