# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_zjw_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc248vbm
_database_code_depnum_ccdc_archive 'CCDC 1974710'
loop_
_audit_author_name
_audit_author_address
jiaweizhang
;yunnan university
China
;
_audit_update_record             
;
2019-12-30 deposited with the CCDC.	2020-05-11 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         ?
_chemical_formula_sum            'C28 H19 Br S'
_chemical_formula_weight         467.40

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'
Br Br -0.2901 2.4595 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   12.91(3)
_cell_length_b                   6.391(14)
_cell_length_c                   25.90(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.40(3)
_cell_angle_gamma                90
_cell_volume                     2124(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1143
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      17.02

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    2.047
_shelx_estimated_absorpt_T_min   0.822
_shelx_estimated_absorpt_T_max   0.923
_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     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16049
_diffrn_reflns_av_unetI/netI     0.1025
_diffrn_reflns_av_R_equivalents  0.1084
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.705
_diffrn_reflns_theta_max         25.247
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3844
_reflns_number_gt                1663
_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    '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)+(0.0900P)²] 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         3844
_refine_ls_number_parameters     271
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1672
_refine_ls_R_factor_gt           0.0644
_refine_ls_wR_factor_ref         0.2052
_refine_ls_wR_factor_gt          0.1582
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.04355(7) 0.86082(14) 0.43167(3) 0.0915(4) Uani 1 1 d . . . . .
S1 S 0.40077(16) 0.2545(4) 0.54085(7) 0.0811(7) Uani 1 1 d . . . . .
C1 C 0.3012(6) 0.4211(12) 0.5101(2) 0.0614(19) Uani 1 1 d . . . . .
C2 C 0.3261(6) 0.6226(14) 0.4957(3) 0.076(2) Uani 1 1 d . . . . .
H2 H 0.394213 0.670609 0.502847 0.091 Uiso 1 1 calc R U . . .
C3 C 0.2507(7) 0.7527(13) 0.4710(3) 0.072(2) Uani 1 1 d . . . . .
H3 H 0.268108 0.887021 0.461156 0.086 Uiso 1 1 calc R U . . .
C4 C 0.1512(6) 0.6836(12) 0.4611(3) 0.068(2) Uani 1 1 d . . . . .
C5 C 0.1277(6) 0.4794(13) 0.4745(3) 0.072(2) Uani 1 1 d . . . . .
H5 H 0.059921 0.430153 0.466951 0.086 Uiso 1 1 calc R U . . .
C6 C 0.2024(6) 0.3501(12) 0.4984(3) 0.0678(19) Uani 1 1 d . . . . .
H6 H 0.185580 0.213590 0.506739 0.081 Uiso 1 1 calc R U . . .
C7 C 0.3862(6) 0.3084(12) 0.6065(3) 0.072(2) Uani 1 1 d . . . . .
H7 H 0.332535 0.398018 0.613181 0.086 Uiso 1 1 calc R U . . .
C8 C 0.4470(5) 0.2297(11) 0.6479(3) 0.0606(18) Uani 1 1 d . . . . .
C9 C 0.5295(6) 0.0709(11) 0.6408(3) 0.0592(18) Uani 1 1 d . . . . .
C10 C 0.6360(6) 0.1009(11) 0.6603(2) 0.0591(19) Uani 1 1 d . . . . .
C11 C 0.6723(6) 0.2849(12) 0.6883(3) 0.066(2) Uani 1 1 d . . . . .
H11 H 0.625788 0.391929 0.693517 0.079 Uiso 1 1 calc R U . . .
C12 C 0.7758(6) 0.3044(13) 0.7077(3) 0.077(2) Uani 1 1 d . . . . .
H12 H 0.798622 0.425638 0.725290 0.092 Uiso 1 1 calc R U . . .
C13 C 0.8463(7) 0.1456(18) 0.7012(4) 0.097(3) Uani 1 1 d . . . . .
H13 H 0.915170 0.156652 0.715835 0.117 Uiso 1 1 calc R U . . .
C14 C 0.8129(7) -0.0292(16) 0.6728(3) 0.088(3) Uani 1 1 d . . . . .
H14 H 0.861177 -0.131787 0.666738 0.106 Uiso 1 1 calc R U . . .
C15 C 0.7104(6) -0.0561(13) 0.6533(3) 0.066(2) Uani 1 1 d . . . . .
C16 C 0.6770(7) -0.2393(13) 0.6244(3) 0.077(2) Uani 1 1 d . . . . .
H16 H 0.724619 -0.342968 0.618196 0.093 Uiso 1 1 calc R U . . .
C17 C 0.5762(8) -0.2593(14) 0.6065(3) 0.087(2) Uani 1 1 d . . . . .
H17 H 0.555125 -0.379287 0.587878 0.104 Uiso 1 1 calc R U . . .
C18 C 0.5013(6) -0.1088(12) 0.6144(3) 0.073(2) Uani 1 1 d . . . . .
H18 H 0.431973 -0.130977 0.601595 0.087 Uiso 1 1 calc R U . . .
C19 C 0.4242(5) 0.2929(13) 0.7002(3) 0.067(2) Uani 1 1 d . . . . .
C20 C 0.3792(5) 0.5001(14) 0.7089(3) 0.079(2) Uani 1 1 d . U . . .
H20 H 0.371789 0.598831 0.682313 0.095 Uiso 1 1 calc R U . . .
C21 C 0.3488(5) 0.5448(13) 0.7563(3) 0.079(2) Uani 1 1 d . U . . .
H21 H 0.318852 0.674604 0.761259 0.095 Uiso 1 1 calc R U . . .
C22 C 0.3605(5) 0.4039(13) 0.7977(3) 0.068(2) Uani 1 1 d . . . . .
C23 C 0.3228(5) 0.4531(15) 0.8479(4) 0.081(2) Uani 1 1 d . . . . .
H23 H 0.290887 0.580831 0.852828 0.097 Uiso 1 1 calc R U . . .
C24 C 0.3349(6) 0.3131(18) 0.8862(3) 0.085(3) Uani 1 1 d . . . . .
H24 H 0.311228 0.341730 0.918048 0.102 Uiso 1 1 calc R U . . .
C25 C 0.3834(7) 0.1234(16) 0.8779(3) 0.086(2) Uani 1 1 d . . . . .
H25 H 0.390718 0.027322 0.905059 0.103 Uiso 1 1 calc R U . . .
C26 C 0.4213(6) 0.0689(14) 0.8320(3) 0.084(2) Uani 1 1 d . . . . .
H26 H 0.454442 -0.058541 0.828314 0.101 Uiso 1 1 calc R U . . .
C27 C 0.4080(5) 0.2105(12) 0.7918(3) 0.0635(19) Uani 1 1 d . . . . .
C28 C 0.4390(5) 0.1568(14) 0.7399(3) 0.074(2) Uani 1 1 d . . . . .
H28 H 0.468991 0.027261 0.734754 0.089 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 C4 1.886(8) . ?
S1 C7 1.765(8) . ?
S1 C1 1.787(8) . ?
C1 C6 1.355(10) . ?
C1 C2 1.388(10) . ?
C2 C3 1.383(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.356(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(10) . ?
C5 C6 1.366(10) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.353(9) . ?
C7 H7 0.9300 . ?
C8 C19 1.476(10) . ?
C8 C9 1.497(10) . ?
C9 C18 1.366(9) . ?
C9 C10 1.423(10) . ?
C10 C15 1.415(9) . ?
C10 C11 1.433(10) . ?
C11 C12 1.380(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.385(11) . ?
C12 H12 0.9300 . ?
C13 C14 1.380(12) . ?
C13 H13 0.9300 . ?
C14 C15 1.373(11) . ?
C14 H14 0.9300 . ?
C15 C16 1.430(11) . ?
C16 C17 1.338(11) . ?
C16 H16 0.9300 . ?
C17 C18 1.395(11) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C28 1.343(10) . ?
C19 C20 1.473(11) . ?
C20 C21 1.360(10) . ?
C20 H20 0.9300 . ?
C21 C22 1.397(10) . ?
C21 H21 0.9300 . ?
C22 C27 1.396(10) . ?
C22 C23 1.472(11) . ?
C23 C24 1.332(11) . ?
C23 H23 0.9300 . ?
C24 C25 1.392(11) . ?
C24 H24 0.9300 . ?
C25 C26 1.381(11) . ?
C25 H25 0.9300 . ?
C26 C27 1.375(10) . ?
C26 H26 0.9300 . ?
C27 C28 1.485(10) . ?
C28 H28 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
C7 S1 C1 99.5(4) . . ?
C6 C1 C2 119.4(7) . . ?
C6 C1 S1 120.8(6) . . ?
C2 C1 S1 119.7(6) . . ?
C3 C2 C1 120.6(7) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 119.7(7) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 119.1(7) . . ?
C3 C4 Br1 121.4(6) . . ?
C5 C4 Br1 119.5(6) . . ?
C6 C5 C4 121.2(7) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C1 C6 C5 119.9(7) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C8 C7 S1 125.2(6) . . ?
C8 C7 H7 117.4 . . ?
S1 C7 H7 117.4 . . ?
C7 C8 C19 117.9(7) . . ?
C7 C8 C9 120.9(7) . . ?
C19 C8 C9 121.0(6) . . ?
C18 C9 C10 118.9(7) . . ?
C18 C9 C8 118.6(7) . . ?
C10 C9 C8 122.5(7) . . ?
C15 C10 C9 120.1(7) . . ?
C15 C10 C11 117.2(7) . . ?
C9 C10 C11 122.6(7) . . ?
C12 C11 C10 120.5(7) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 120.8(8) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 119.2(8) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C15 C14 C13 121.9(8) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C14 C15 C10 120.3(8) . . ?
C14 C15 C16 121.1(8) . . ?
C10 C15 C16 118.5(7) . . ?
C17 C16 C15 119.0(8) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C16 C17 C18 123.1(9) . . ?
C16 C17 H17 118.4 . . ?
C18 C17 H17 118.4 . . ?
C9 C18 C17 120.2(8) . . ?
C9 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C28 C19 C20 119.4(7) . . ?
C28 C19 C8 120.0(7) . . ?
C20 C19 C8 120.5(7) . . ?
C21 C20 C19 118.9(8) . . ?
C21 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
C20 C21 C22 122.7(8) . . ?
C20 C21 H21 118.6 . . ?
C22 C21 H21 118.6 . . ?
C27 C22 C21 119.9(8) . . ?
C27 C22 C23 118.6(7) . . ?
C21 C22 C23 121.5(8) . . ?
C24 C23 C22 119.4(8) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C23 C24 C25 119.2(9) . . ?
C23 C24 H24 120.4 . . ?
C25 C24 H24 120.4 . . ?
C26 C25 C24 124.1(8) . . ?
C26 C25 H25 118.0 . . ?
C24 C25 H25 118.0 . . ?
C27 C26 C25 117.4(9) . . ?
C27 C26 H26 121.3 . . ?
C25 C26 H26 121.3 . . ?
C26 C27 C22 121.3(8) . . ?
C26 C27 C28 120.6(8) . . ?
C22 C27 C28 118.0(7) . . ?
C19 C28 C27 120.9(8) . . ?
C19 C28 H28 119.6 . . ?
C27 C28 H28 119.6 . . ?

_refine_diff_density_max         0.526
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.068



####################################################################### 
# 
# 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_hz_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc248vcn
_database_code_depnum_ccdc_archive 'CCDC 1974711'
loop_
_audit_author_name
_audit_author_address
jiaweizhang
;yunnan university
China
;
_audit_update_record             
;
2019-12-30 deposited with the CCDC.	2020-05-11 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         ?
_chemical_formula_sum            'C22 H20 S'
_chemical_formula_weight         316.44

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   5.87(3)
_cell_length_b                   9.46(4)
_cell_length_c                   16.79(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.493(5)
_cell_angle_gamma                90
_cell_volume                     931(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1298
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      21.85

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.129
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.171
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.981
_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     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7583
_diffrn_reflns_av_unetI/netI     0.0824
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.472
_diffrn_reflns_theta_max         27.442
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             4119
_reflns_number_gt                2396
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.831
_reflns_Friedel_fraction_max     0.933
_reflns_Friedel_fraction_full    0.969

_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)+(0.0500P)²] 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 770 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4119
_refine_ls_number_parameters     210
_refine_ls_number_restraints     57
_refine_ls_R_factor_all          0.1074
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1322
_refine_ls_wR_factor_gt          0.1116
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.985
_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 0.4319(2) 0.20154(13) 0.68490(7) 0.0732(4) Uani 1 1 d . . . . .
C1 C 0.5987(8) 0.2027(6) 0.5967(2) 0.0621(10) Uani 1 1 d . U . . .
C2 C 0.7904(10) 0.1172(6) 0.5956(3) 0.0795(13) Uani 1 1 d . U . . .
H2 H 0.835063 0.064492 0.640339 0.095 Uiso 1 1 calc R U . . .
C3 C 0.9158(10) 0.1105(7) 0.5271(3) 0.0894(15) Uani 1 1 d D U . . .
H3 H 1.041451 0.050603 0.526575 0.107 Uiso 1 1 calc R U . . .
C4 C 0.8599(8) 0.1900(8) 0.4598(3) 0.0817(12) Uani 1 1 d D U . . .
C5 C 0.6672(9) 0.2768(7) 0.4616(3) 0.0841(14) Uani 1 1 d D U . . .
H5 H 0.624436 0.331098 0.417274 0.101 Uiso 1 1 calc R U . . .
C6 C 0.5381(9) 0.2823(6) 0.5299(3) 0.0807(14) Uani 1 1 d . U . . .
H6 H 0.410034 0.340185 0.530320 0.097 Uiso 1 1 calc R U . . .
C7 C 1.0080(10) 0.1846(10) 0.3856(3) 0.130(2) Uani 1 1 d . U . . .
H7A H 1.006020 0.090505 0.364206 0.195 Uiso 1 1 calc R U . . .
H7B H 1.162008 0.210744 0.400687 0.195 Uiso 1 1 calc R U . . .
H7C H 0.947637 0.249252 0.345960 0.195 Uiso 1 1 calc R U . . .
C8 C 0.4238(8) 0.3831(4) 0.7106(2) 0.0581(11) Uani 1 1 d . U . . .
H8 H 0.485776 0.446959 0.675423 0.070 Uiso 1 1 calc R U . . .
C9 C 0.3352(7) 0.4362(5) 0.7771(2) 0.0502(8) Uani 1 1 d . U . . .
C10 C 0.2199(7) 0.3409(4) 0.8357(2) 0.0487(7) Uani 1 1 d . U . . .
C11 C 0.3055(8) 0.3275(5) 0.9153(3) 0.0562(8) Uani 1 1 d . U . . .
C12 C 0.1918(10) 0.2352(5) 0.9664(3) 0.0795(11) Uani 1 1 d D U . . .
H12 H 0.247179 0.224872 1.018850 0.095 Uiso 1 1 calc R U . . .
C13 C -0.0016(10) 0.1587(5) 0.9405(4) 0.0895(13) Uani 1 1 d D U . . .
H13 H -0.073471 0.098505 0.975323 0.107 Uiso 1 1 calc R U . . .
C14 C -0.0845(9) 0.1735(5) 0.8630(4) 0.0840(12) Uani 1 1 d D U . . .
H14 H -0.213311 0.123127 0.845484 0.101 Uiso 1 1 calc R U . . .
C15 C 0.0241(8) 0.2643(5) 0.8099(3) 0.0627(9) Uani 1 1 d . U . . .
H15 H -0.033636 0.273756 0.757731 0.075 Uiso 1 1 calc R U . . .
C16 C 0.5125(9) 0.4119(6) 0.9474(3) 0.0765(12) Uani 1 1 d . U . . .
H16A H 0.616037 0.426356 0.905416 0.115 Uiso 1 1 calc R U . . .
H16B H 0.588357 0.360571 0.990146 0.115 Uiso 1 1 calc R U . . .
H16C H 0.462844 0.501836 0.966730 0.115 Uiso 1 1 calc R U . . .
C17 C 0.3423(7) 0.5927(5) 0.7933(2) 0.0477(8) Uani 1 1 d . U . . .
C18 C 0.5215(7) 0.6788(5) 0.7684(2) 0.0607(10) Uani 1 1 d . U . . .
H18 H 0.643885 0.637942 0.743499 0.073 Uiso 1 1 calc R U . . .
C19 C 0.5180(9) 0.8255(5) 0.7805(3) 0.0710(12) Uani 1 1 d . U . . .
H19 H 0.635773 0.880826 0.762114 0.085 Uiso 1 1 calc R U . . .
C20 C 0.3406(9) 0.8897(5) 0.8198(3) 0.0670(11) Uani 1 1 d . U . . .
H20 H 0.338736 0.987050 0.827568 0.080 Uiso 1 1 calc R U . . .
C21 C 0.1666(8) 0.8051(5) 0.8471(3) 0.0625(11) Uani 1 1 d . U . . .
H21 H 0.049917 0.846235 0.874893 0.075 Uiso 1 1 calc R U . . .
C22 C 0.1639(7) 0.6584(4) 0.8334(2) 0.0524(9) Uani 1 1 d . U . . .
H22 H 0.043610 0.604242 0.850817 0.063 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
S1 C8 1.772(9) . ?
S1 C1 1.810(7) . ?
C1 C6 1.385(8) . ?
C1 C2 1.386(8) . ?
C2 C3 1.393(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.385(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.398(9) . ?
C4 C7 1.550(8) . ?
C5 C6 1.403(8) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.349(7) . ?
C8 H8 0.9300 . ?
C9 C17 1.505(9) . ?
C9 C10 1.516(7) . ?
C10 C15 1.410(7) . ?
C10 C11 1.414(8) . ?
C11 C12 1.412(7) . ?
C11 C16 1.531(8) . ?
C12 C13 1.399(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(10) . ?
C13 H13 0.9300 . ?
C14 C15 1.410(7) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.408(7) . ?
C17 C22 1.413(7) . ?
C18 C19 1.403(9) . ?
C18 H18 0.9300 . ?
C19 C20 1.395(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.390(8) . ?
C20 H20 0.9300 . ?
C21 C22 1.407(9) . ?
C21 H21 0.9300 . ?
C22 H22 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
C8 S1 C1 102.4(2) . . ?
C6 C1 C2 119.1(4) . . ?
C6 C1 S1 122.5(4) . . ?
C2 C1 S1 118.4(4) . . ?
C1 C2 C3 119.7(5) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 122.3(6) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C3 C4 C5 117.6(5) . . ?
C3 C4 C7 121.1(6) . . ?
C5 C4 C7 121.3(6) . . ?
C4 C5 C6 120.4(5) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 120.9(6) . . ?
C1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 S1 125.3(3) . . ?
C9 C8 H8 117.3 . . ?
S1 C8 H8 117.3 . . ?
C8 C9 C17 120.5(4) . . ?
C8 C9 C10 121.0(5) . . ?
C17 C9 C10 118.6(4) . . ?
C15 C10 C11 119.7(4) . . ?
C15 C10 C9 119.2(5) . . ?
C11 C10 C9 121.1(4) . . ?
C12 C11 C10 118.2(5) . . ?
C12 C11 C16 119.8(5) . . ?
C10 C11 C16 122.0(4) . . ?
C13 C12 C11 122.0(6) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C14 C13 C12 119.3(5) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 120.6(6) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C10 120.2(5) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C22 117.7(5) . . ?
C18 C17 C9 122.1(4) . . ?
C22 C17 C9 120.2(4) . . ?
C19 C18 C17 120.9(4) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C20 C19 C18 121.0(4) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C21 C20 C19 118.6(5) . . ?
C21 C20 H20 120.7 . . ?
C19 C20 H20 120.7 . . ?
C20 C21 C22 121.1(5) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C21 C22 C17 120.6(4) . . ?
C21 C22 H22 119.7 . . ?
C17 C22 H22 119.7 . . ?

_refine_diff_density_max         0.206
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.036



