# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_compound3e_AS011
_database_code_depnum_ccdc_archive 'CCDC 1958921'
loop_
_audit_author_name
_audit_author_address
'Katherine Robertson' 'Saint Marys University'
_audit_update_record             
;
2021-01-31 deposited with the CCDC.	2021-02-09 downloaded from the CCDC.
;

#==============================================================================

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H19 B O2 S'
_chemical_formula_sum            'C18 H19 B O2 S'
_chemical_formula_weight         310.20

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'
B B 0.0013 0.0007 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   11.4270(10)
_cell_length_b                   10.2820(9)
_cell_length_c                   13.6992(12)
_cell_angle_alpha                90
_cell_angle_beta                 99.468(3)
_cell_angle_gamma                90
_cell_volume                     1587.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9790
_cell_measurement_theta_min      3.62
_cell_measurement_theta_max      46.27

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.302
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.128
_exptl_absorpt_coefficient_mu    0.207
_shelx_estimated_absorpt_T_min   0.940
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6987
_exptl_absorpt_correction_T_max  0.7493
_exptl_absorpt_process_details   
;
SADABS--2016/2 -- Bruker AXS area detector scaling and absorption correction
(Bruker AXS Inc., 2016)
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_source            'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device       'κ--geometry diffractometer'
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.41
_diffrn_reflns_number            135411
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.615
_diffrn_reflns_theta_max         46.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             14090
_reflns_number_gt                10851
_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       
;
Bruker Instrument Service, BIS, v.6.2.10 (Bruker AXS Inc., 2018)
;
_computing_cell_refinement       'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_data_reduction        'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_bruker_data_scaling   
;
SADABS--2016/2 -- Bruker AXS area detector scaling and absorption correction
(Bruker AXS Inc., 2016)
;
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (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)+(0.0594P)²+0.3006P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'dual space'
_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         14090
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1297
_refine_ls_wR_factor_gt          0.1119
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.17984(2) 0.50116(2) 0.15616(2) 0.01794(3) Uani 1 1 d . . . . .
O1 O 0.37980(4) 0.35987(4) 0.20002(4) 0.01655(7) Uani 1 1 d . . . . .
O2 O 0.24470(4) 0.20748(4) 0.13303(3) 0.01543(6) Uani 1 1 d . . . . .
B1 B 0.26191(5) 0.32642(5) 0.17825(4) 0.01322(8) Uani 1 1 d . . . . .
C1 C -0.03343(5) 0.49883(5) 0.21660(4) 0.01416(7) Uani 1 1 d . . . . .
C2 C 0.00544(5) 0.56741(6) 0.30357(4) 0.01751(8) Uani 1 1 d . . . . .
H2 H -0.048480 0.616033 0.335012 0.021 Uiso 1 1 calc R U . . .
C3 C 0.12506(5) 0.56261(6) 0.34285(4) 0.01850(9) Uani 1 1 d . . . . .
H3 H 0.154864 0.610408 0.400981 0.022 Uiso 1 1 calc R U . . .
C4 C 0.20188(5) 0.48703(5) 0.29655(4) 0.01609(8) Uani 1 1 d . . . . .
H4 H 0.283691 0.485370 0.324392 0.019 Uiso 1 1 calc R U . . .
C5 C 0.16361(4) 0.41368(5) 0.21098(4) 0.01327(7) Uani 1 1 d . . . . .
C6 C 0.04217(4) 0.42288(5) 0.16777(4) 0.01262(6) Uani 1 1 d . . . . .
C7 C -0.02337(4) 0.36917(5) 0.07558(4) 0.01342(7) Uani 1 1 d . . . . .
C8 C 0.01645(5) 0.29489(6) 0.00173(4) 0.01602(8) Uani 1 1 d . . . . .
H8 H 0.097736 0.271181 0.008448 0.019 Uiso 1 1 calc R U . . .
C9 C -0.06247(6) 0.25583(6) -0.08123(4) 0.01917(9) Uani 1 1 d . . . . .
H9 H -0.034675 0.204882 -0.130556 0.023 Uiso 1 1 calc R U . . .
C10 C -0.18219(6) 0.29047(7) -0.09310(4) 0.02046(10) Uani 1 1 d . . . . .
H10 H -0.235147 0.262351 -0.150016 0.025 Uiso 1 1 calc R U . . .
C11 C -0.22409(5) 0.36556(6) -0.02234(5) 0.01945(9) Uani 1 1 d . . . . .
H11 H -0.305215 0.390295 -0.030417 0.023 Uiso 1 1 calc R U . . .
C12 C -0.14429(5) 0.40423(5) 0.06135(4) 0.01572(8) Uani 1 1 d . . . . .
C13 C 0.44836(4) 0.24540(5) 0.18068(4) 0.01519(7) Uani 1 1 d . . . . .
C14 C 0.35725(5) 0.16968(5) 0.10432(4) 0.01526(7) Uani 1 1 d . . . . .
C15 C 0.48225(6) 0.17388(7) 0.27856(5) 0.02120(10) Uani 1 1 d . . . . .
H15A H 0.527038 0.232476 0.327430 0.032 Uiso 1 1 calc R U . . .
H15B H 0.531324 0.098265 0.268964 0.032 Uiso 1 1 calc R U . . .
H15C H 0.410212 0.144858 0.302289 0.032 Uiso 1 1 calc R U . . .
C16 C 0.55850(6) 0.28981(7) 0.14160(6) 0.02537(12) Uani 1 1 d . . . . .
H16A H 0.535706 0.349488 0.085943 0.038 Uiso 1 1 calc R U . . .
H16B H 0.599042 0.214114 0.119280 0.038 Uiso 1 1 calc R U . . .
H16C H 0.611910 0.334505 0.194324 0.038 Uiso 1 1 calc R U . . .
C17 C 0.36804(6) 0.02261(6) 0.11000(6) 0.02331(11) Uani 1 1 d . . . . .
H17A H 0.354770 -0.007056 0.175275 0.035 Uiso 1 1 calc R U . . .
H17B H 0.447621 -0.003344 0.099682 0.035 Uiso 1 1 calc R U . . .
H17C H 0.308695 -0.016703 0.058693 0.035 Uiso 1 1 calc R U . . .
C18 C 0.35398(7) 0.21665(8) -0.00147(5) 0.02576(12) Uani 1 1 d . . . . .
H18A H 0.284787 0.179368 -0.044032 0.039 Uiso 1 1 calc R U . . .
H18B H 0.426492 0.189062 -0.025131 0.039 Uiso 1 1 calc R U . . .
H18C H 0.348560 0.311767 -0.003366 0.039 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 C12 1.7374(6) . ?
S1 C1 1.7405(6) . ?
O1 B1 1.3747(7) . ?
O1 C13 1.4621(7) . ?
O2 B1 1.3704(7) . ?
O2 C14 1.4582(7) . ?
B1 C5 1.5599(7) . ?
C1 C2 1.3928(8) . ?
C1 C6 1.4119(7) . ?
C2 C3 1.3851(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.3999(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.4020(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.4195(7) . ?
C6 C7 1.4662(7) . ?
C7 C8 1.4019(8) . ?
C7 C12 1.4103(7) . ?
C8 C9 1.3888(8) . ?
C8 H8 0.9500 . ?
C9 C10 1.3970(9) . ?
C9 H9 0.9500 . ?
C10 C11 1.3848(10) . ?
C10 H10 0.9500 . ?
C11 C12 1.4001(8) . ?
C11 H11 0.9500 . ?
C13 C16 1.5169(8) . ?
C13 C15 1.5224(9) . ?
C13 C14 1.5575(8) . ?
C14 C17 1.5182(8) . ?
C14 C18 1.5222(9) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 S1 C1 91.32(3) . . ?
B1 O1 C13 107.12(4) . . ?
B1 O2 C14 107.00(4) . . ?
O2 B1 O1 112.58(5) . . ?
O2 B1 C5 125.92(5) . . ?
O1 B1 C5 121.33(5) . . ?
C2 C1 C6 123.46(5) . . ?
C2 C1 S1 123.12(4) . . ?
C6 C1 S1 113.42(4) . . ?
C3 C2 C1 118.02(5) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C2 C3 C4 119.74(5) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 123.02(5) . . ?
C3 C4 H4 118.5 . . ?
C5 C4 H4 118.5 . . ?
C4 C5 C6 117.50(5) . . ?
C4 C5 B1 114.17(4) . . ?
C6 C5 B1 128.27(4) . . ?
C1 C6 C5 118.15(5) . . ?
C1 C6 C7 110.53(4) . . ?
C5 C6 C7 131.29(4) . . ?
C8 C7 C12 117.81(5) . . ?
C8 C7 C6 130.27(5) . . ?
C12 C7 C6 111.89(5) . . ?
C9 C8 C7 120.26(5) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 120.87(6) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 120.36(5) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 118.55(5) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
C11 C12 C7 122.14(5) . . ?
C11 C12 S1 125.05(5) . . ?
C7 C12 S1 112.80(4) . . ?
O1 C13 C16 108.79(5) . . ?
O1 C13 C15 107.19(5) . . ?
C16 C13 C15 110.53(5) . . ?
O1 C13 C14 101.84(4) . . ?
C16 C13 C14 114.53(5) . . ?
C15 C13 C14 113.28(5) . . ?
O2 C14 C17 108.63(5) . . ?
O2 C14 C18 106.72(5) . . ?
C17 C14 C18 110.72(5) . . ?
O2 C14 C13 101.97(4) . . ?
C17 C14 C13 115.07(5) . . ?
C18 C14 C13 112.95(5) . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 O2 B1 O1 -12.09(6) . . . . ?
C14 O2 B1 C5 172.61(5) . . . . ?
C13 O1 B1 O2 -8.78(6) . . . . ?
C13 O1 B1 C5 166.77(5) . . . . ?
C12 S1 C1 C2 177.20(5) . . . . ?
C12 S1 C1 C6 -1.61(4) . . . . ?
C6 C1 C2 C3 1.33(9) . . . . ?
S1 C1 C2 C3 -177.36(5) . . . . ?
C1 C2 C3 C4 -1.91(9) . . . . ?
C2 C3 C4 C5 -0.35(9) . . . . ?
C3 C4 C5 C6 3.17(8) . . . . ?
C3 C4 C5 B1 -174.27(5) . . . . ?
O2 B1 C5 C4 147.01(6) . . . . ?
O1 B1 C5 C4 -27.92(7) . . . . ?
O2 B1 C5 C6 -30.11(9) . . . . ?
O1 B1 C5 C6 154.97(5) . . . . ?
C2 C1 C6 C5 1.51(8) . . . . ?
S1 C1 C6 C5 -179.69(4) . . . . ?
C2 C1 C6 C7 -176.70(5) . . . . ?
S1 C1 C6 C7 2.10(5) . . . . ?
C4 C5 C6 C1 -3.63(7) . . . . ?
B1 C5 C6 C1 173.40(5) . . . . ?
C4 C5 C6 C7 174.14(5) . . . . ?
B1 C5 C6 C7 -8.83(9) . . . . ?
C1 C6 C7 C8 176.20(5) . . . . ?
C5 C6 C7 C8 -1.70(9) . . . . ?
C1 C6 C7 C12 -1.59(6) . . . . ?
C5 C6 C7 C12 -179.49(5) . . . . ?
C12 C7 C8 C9 -1.28(8) . . . . ?
C6 C7 C8 C9 -178.96(5) . . . . ?
C7 C8 C9 C10 0.54(9) . . . . ?
C8 C9 C10 C11 0.52(9) . . . . ?
C9 C10 C11 C12 -0.77(9) . . . . ?
C10 C11 C12 C7 -0.01(9) . . . . ?
C10 C11 C12 S1 178.53(5) . . . . ?
C8 C7 C12 C11 1.03(8) . . . . ?
C6 C7 C12 C11 179.12(5) . . . . ?
C8 C7 C12 S1 -177.67(4) . . . . ?
C6 C7 C12 S1 0.42(6) . . . . ?
C1 S1 C12 C11 -178.01(5) . . . . ?
C1 S1 C12 C7 0.65(4) . . . . ?
B1 O1 C13 C16 145.35(5) . . . . ?
B1 O1 C13 C15 -95.12(5) . . . . ?
B1 O1 C13 C14 24.06(6) . . . . ?
B1 O2 C14 C17 147.93(5) . . . . ?
B1 O2 C14 C18 -92.65(6) . . . . ?
B1 O2 C14 C13 26.02(5) . . . . ?
O1 C13 C14 O2 -30.06(5) . . . . ?
C16 C13 C14 O2 -147.28(5) . . . . ?
C15 C13 C14 O2 84.70(5) . . . . ?
O1 C13 C14 C17 -147.43(5) . . . . ?
C16 C13 C14 C17 95.35(7) . . . . ?
C15 C13 C14 C17 -32.66(7) . . . . ?
O1 C13 C14 C18 84.09(5) . . . . ?
C16 C13 C14 C18 -33.13(7) . . . . ?
C15 C13 C14 C18 -161.15(5) . . . . ?

_refine_diff_density_max         0.908
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_compound11c_AS025B
_database_code_depnum_ccdc_archive 'CCDC 2020652'
loop_
_audit_author_name
_audit_author_address
'Katherine Robertson' 'Saint Marys University'
_audit_update_record             
;
2021-01-31 deposited with the CCDC.	2021-02-09 downloaded from the CCDC.
;

#==============================================================================

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H23 N O S2'
_chemical_formula_sum            'C19 H23 N O S2'
_chemical_formula_weight         345.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.6260(5)
_cell_length_b                   9.2018(5)
_cell_length_c                   22.6467(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1797.58(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9817
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      38.57

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.265
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.068
_exptl_absorpt_coefficient_mu    0.300
_shelx_estimated_absorpt_T_min   0.925
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6501
_exptl_absorpt_correction_T_max  0.7478
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_source            'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device       'κ--geometry diffractometer'
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.41
_diffrn_reflns_number            75947
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.389
_diffrn_reflns_theta_max         33.141
_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 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6840
_reflns_number_gt                6112
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
Bruker Instrument Service, BIS, v.6.2.10 (Bruker AXS Inc., 2018)
;
_computing_cell_refinement       'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_data_reduction        'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (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)+(0.0345P)²+0.5513P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'dual space'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2398 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.019(15)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         6840
_refine_ls_number_parameters     347
_refine_ls_number_restraints     663
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.0894
_refine_ls_wR_factor_gt          0.0849
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.050
_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
S2 S 0.66185(6) 0.37200(4) 0.28116(2) 0.02258(10) Uani 1 1 d . . . . .
O1A O 0.5252(4) 0.3032(4) 0.24253(18) 0.0268(7) Uani 0.5 1 d . . P . .
O1B O 0.5719(4) 0.2636(3) 0.25327(16) 0.0205(6) Uani 0.5 1 d . . P . .
N1 N 0.58833(19) 0.52871(16) 0.30143(8) 0.0217(3) Uani 1 1 d D . . . .
H1 H 0.542(4) 0.576(3) 0.2709(13) 0.047(8) Uiso 1 1 d . . . . .
S1A S 0.93592(12) 0.69854(16) 0.49900(5) 0.0400(3) Uani 0.867(3) 1 d D U P A 1
C1A C 0.8130(3) 0.5598(3) 0.47516(12) 0.0298(5) Uani 0.867(3) 1 d D U P A 1
C2A C 0.8079(4) 0.4229(4) 0.50124(12) 0.0354(6) Uani 0.867(3) 1 d D U P A 1
H2A H 0.874379 0.398639 0.533187 0.042 Uiso 0.867(3) 1 calc R U P A 1
C3A C 0.7038(4) 0.3241(3) 0.47934(11) 0.0361(6) Uani 0.867(3) 1 d D U P A 1
H3A H 0.699338 0.229112 0.495643 0.043 Uiso 0.867(3) 1 calc R U P A 1
C4A C 0.6036(3) 0.3623(2) 0.43300(10) 0.0272(5) Uani 0.867(3) 1 d D U P A 1
H4A H 0.530427 0.292911 0.419300 0.033 Uiso 0.867(3) 1 calc R U P A 1
C5A C 0.6084(3) 0.4988(2) 0.40653(11) 0.0204(4) Uani 0.867(3) 1 d D U P A 1
C6A C 0.7193(3) 0.6009(3) 0.42684(14) 0.0218(5) Uani 0.867(3) 1 d D U P A 1
C13A C 0.4986(3) 0.5359(2) 0.35589(11) 0.0182(4) Uani 0.867(3) 1 d D U P A 1
H13A H 0.468570 0.640055 0.361260 0.022 Uiso 0.867(3) 1 calc R U P A 1
C14A C 0.3477(3) 0.4494(2) 0.35350(9) 0.0213(4) Uani 0.867(3) 1 d D U P A 1
H14A H 0.372414 0.344308 0.353991 0.026 Uiso 0.867(3) 1 calc R U P A 1
H14B H 0.293968 0.470843 0.315870 0.026 Uiso 0.867(3) 1 calc R U P A 1
C15A C 0.2387(3) 0.4837(3) 0.40485(11) 0.0289(5) Uani 0.867(3) 1 d D U P A 1
H15A H 0.288320 0.456185 0.442136 0.043 Uiso 0.867(3) 1 calc R U P A 1
H15B H 0.142070 0.428852 0.400099 0.043 Uiso 0.867(3) 1 calc R U P A 1
H15C H 0.215723 0.587973 0.405237 0.043 Uiso 0.867(3) 1 calc R U P A 1
S1B S 0.9822(8) 0.7434(6) 0.4944(2) 0.0249(12) Uani 0.133(3) 1 d D U P A 2
C1B C 0.8721(19) 0.5947(13) 0.4776(7) 0.022(2) Uani 0.133(3) 1 d D U P A 2
C2B C 0.893(2) 0.4618(15) 0.5067(7) 0.030(2) Uani 0.133(3) 1 d D U P A 2
H2B H 0.968636 0.450348 0.536863 0.036 Uiso 0.133(3) 1 calc R U P A 2
C3B C 0.800(2) 0.3505(18) 0.4899(7) 0.029(2) Uani 0.133(3) 1 d D U P A 2
H3B H 0.816891 0.257602 0.507075 0.035 Uiso 0.133(3) 1 calc R U P A 2
C4B C 0.681(2) 0.3654(16) 0.4486(6) 0.026(2) Uani 0.133(3) 1 d D U P A 2
H4B H 0.614386 0.285973 0.440233 0.031 Uiso 0.133(3) 1 calc R U P A 2
C5B C 0.661(2) 0.5018(17) 0.4191(7) 0.024(2) Uani 0.133(3) 1 d D U P A 2
C6B C 0.759(2) 0.6103(17) 0.4354(9) 0.023(2) Uani 0.133(3) 1 d D U P A 2
C13B C 0.5324(16) 0.5173(15) 0.3734(6) 0.016(2) Uani 0.133(3) 1 d D U P A 2
H13B H 0.487436 0.615255 0.381839 0.019 Uiso 0.133(3) 1 calc R U P A 2
C14B C 0.3969(16) 0.4100(14) 0.3885(7) 0.025(2) Uani 0.133(3) 1 d D U P A 2
H14C H 0.428490 0.309773 0.378138 0.030 Uiso 0.133(3) 1 calc R U P A 2
H14D H 0.376587 0.412940 0.431527 0.030 Uiso 0.133(3) 1 calc R U P A 2
C15B C 0.253(2) 0.447(2) 0.3564(9) 0.037(3) Uani 0.133(3) 1 d D U P A 2
H15D H 0.194348 0.518931 0.379149 0.056 Uiso 0.133(3) 1 calc R U P A 2
H15E H 0.190620 0.359370 0.351073 0.056 Uiso 0.133(3) 1 calc R U P A 2
H15F H 0.279877 0.487859 0.317725 0.056 Uiso 0.133(3) 1 calc R U P A 2
C7 C 0.7552(2) 0.7521(2) 0.40864(9) 0.0245(4) Uani 1 1 d D U . . .
C8 C 0.6915(2) 0.8344(2) 0.36261(10) 0.0270(4) Uani 1 1 d . U . . .
H8 H 0.617932 0.791631 0.336694 0.032 Uiso 1 1 calc R U . . .
C9 C 0.7356(3) 0.9785(2) 0.35470(12) 0.0341(5) Uani 1 1 d . U . . .
H9 H 0.690323 1.033427 0.323675 0.041 Uiso 1 1 calc R U . . .
C10 C 0.8445(3) 1.0434(3) 0.39123(12) 0.0403(6) Uani 1 1 d . U . . .
H10 H 0.872121 1.142340 0.385454 0.048 Uiso 1 1 calc R U . . .
C11 C 0.9124(3) 0.9644(3) 0.43586(12) 0.0439(6) Uani 1 1 d . U . . .
H11 H 0.988377 1.007472 0.460665 0.053 Uiso 1 1 calc R U . . .
C12 C 0.8678(2) 0.8194(3) 0.44417(9) 0.0332(5) Uani 1 1 d D U . . .
C16 C 0.8001(2) 0.43909(18) 0.22596(9) 0.0239(4) Uani 1 1 d . . . . .
C17A C 0.8972(6) 0.3099(5) 0.2033(2) 0.0262(9) Uani 0.5 1 d D . P B 1
H17A H 0.962173 0.341829 0.170246 0.039 Uiso 0.5 1 calc R U P B 1
H17B H 0.827794 0.232173 0.189958 0.039 Uiso 0.5 1 calc R U P B 1
H17C H 0.963272 0.273478 0.235224 0.039 Uiso 0.5 1 calc R U P B 1
C18A C 0.7025(5) 0.4948(4) 0.16896(17) 0.0253(7) Uani 0.5 1 d D . P B 1
H18A H 0.640619 0.579996 0.179935 0.038 Uiso 0.5 1 calc R U P B 1
H18B H 0.633563 0.417056 0.155376 0.038 Uiso 0.5 1 calc R U P B 1
H18C H 0.774341 0.521114 0.137192 0.038 Uiso 0.5 1 calc R U P B 1
C19A C 0.9029(5) 0.5605(5) 0.2463(2) 0.0297(8) Uani 0.5 1 d D . P B 1
H19A H 0.952888 0.533123 0.283558 0.045 Uiso 0.5 1 calc R U P B 1
H19B H 0.840562 0.648326 0.252382 0.045 Uiso 0.5 1 calc R U P B 1
H19C H 0.982320 0.579504 0.216381 0.045 Uiso 0.5 1 calc R U P B 1
C17B C 0.8342(6) 0.3086(5) 0.1900(2) 0.0250(8) Uani 0.5 1 d D . P B 2
H17D H 0.752085 0.295063 0.160626 0.038 Uiso 0.5 1 calc R U P B 2
H17E H 0.839245 0.223110 0.215732 0.038 Uiso 0.5 1 calc R U P B 2
H17F H 0.933860 0.321345 0.169888 0.038 Uiso 0.5 1 calc R U P B 2
C18B C 0.7517(6) 0.5704(5) 0.1964(2) 0.0326(9) Uani 0.5 1 d D . P B 2
H18D H 0.826651 0.594791 0.165378 0.049 Uiso 0.5 1 calc R U P B 2
H18E H 0.746400 0.650163 0.224985 0.049 Uiso 0.5 1 calc R U P B 2
H18F H 0.649314 0.555501 0.178652 0.049 Uiso 0.5 1 calc R U P B 2
C19B C 0.9389(5) 0.4660(4) 0.2722(2) 0.0290(8) Uani 0.5 1 d D . P B 2
H19D H 1.032540 0.495292 0.250755 0.043 Uiso 0.5 1 calc R U P B 2
H19E H 0.959461 0.376111 0.294042 0.043 Uiso 0.5 1 calc R U P B 2
H19F H 0.909263 0.542920 0.299890 0.043 Uiso 0.5 1 calc R U P B 2


_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
S2 O1B 1.413(3) . ?
S2 O1A 1.599(4) . ?
S2 N1 1.6409(15) . ?
S2 C16 1.835(2) . ?
O1A O1B 0.595(4) . ?
N1 C13A 1.458(3) . ?
N1 C13B 1.703(14) . ?
N1 H1 0.91(3) . ?
S1A C1A 1.745(3) . ?
S1A C12 1.768(3) . ?
C1A C2A 1.392(4) . ?
C1A C6A 1.412(4) . ?
C2A C3A 1.370(5) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.404(4) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.392(3) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.418(4) . ?
C5A C13A 1.527(3) . ?
C6A C7 1.484(3) . ?
C13A C14A 1.527(3) . ?
C13A H13A 1.0000 . ?
C14A C15A 1.529(3) . ?
C14A H14A 0.9900 . ?
C14A H14B 0.9900 . ?
C15A H15A 0.9800 . ?
C15A H15B 0.9800 . ?
C15A H15C 0.9800 . ?
S1B C12 1.660(5) . ?
S1B C1B 1.709(12) . ?
C1B C6B 1.370(17) . ?
C1B C2B 1.401(16) . ?
C2B C3B 1.355(19) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.395(18) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.434(17) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.365(18) . ?
C5B C13B 1.520(17) . ?
C6B C7 1.440(14) . ?
C13B C14B 1.568(16) . ?
C13B H13B 1.0000 . ?
C14B C15B 1.476(18) . ?
C14B H14C 0.9900 . ?
C14B H14D 0.9900 . ?
C15B H15D 0.9800 . ?
C15B H15E 0.9800 . ?
C15B H15F 0.9800 . ?
C7 C8 1.401(3) . ?
C7 C12 1.405(3) . ?
C8 C9 1.391(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.376(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.401(4) . ?
C11 H11 0.9500 . ?
C16 C18B 1.444(4) . ?
C16 C17B 1.480(5) . ?
C16 C19A 1.499(4) . ?
C16 C17A 1.542(5) . ?
C16 C19B 1.609(4) . ?
C16 C18A 1.624(4) . ?
C17A H17A 0.9800 . ?
C17A H17B 0.9800 . ?
C17A H17C 0.9800 . ?
C18A H18A 0.9800 . ?
C18A H18B 0.9800 . ?
C18A H18C 0.9800 . ?
C19A H19A 0.9800 . ?
C19A H19B 0.9800 . ?
C19A H19C 0.9800 . ?
C17B H17D 0.9800 . ?
C17B H17E 0.9800 . ?
C17B H17F 0.9800 . ?
C18B H18D 0.9800 . ?
C18B H18E 0.9800 . ?
C18B H18F 0.9800 . ?
C19B H19D 0.9800 . ?
C19B H19E 0.9800 . ?
C19B H19F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1B S2 O1A 21.68(15) . . ?
O1B S2 N1 122.23(16) . . ?
O1A S2 N1 102.48(16) . . ?
O1B S2 C16 106.86(16) . . ?
O1A S2 C16 103.88(16) . . ?
N1 S2 C16 98.40(8) . . ?
O1B O1A S2 61.3(6) . . ?
O1A O1B S2 97.1(6) . . ?
C13A N1 S2 118.81(13) . . ?
S2 N1 C13B 108.8(5) . . ?
C13A N1 H1 113(2) . . ?
S2 N1 H1 112.3(19) . . ?
C13B N1 H1 129(2) . . ?
C1A S1A C12 92.35(12) . . ?
C2A C1A C6A 123.6(3) . . ?
C2A C1A S1A 123.4(2) . . ?
C6A C1A S1A 113.1(2) . . ?
C3A C2A C1A 117.9(2) . . ?
C3A C2A H2A 121.1 . . ?
C1A C2A H2A 121.1 . . ?
C2A C3A C4A 120.5(2) . . ?
C2A C3A H3A 119.7 . . ?
C4A C3A H3A 119.7 . . ?
C5A C4A C3A 121.9(3) . . ?
C5A C4A H4A 119.0 . . ?
C3A C4A H4A 119.0 . . ?
C4A C5A C6A 118.6(2) . . ?
C4A C5A C13A 120.5(2) . . ?
C6A C5A C13A 120.94(19) . . ?
C1A C6A C5A 117.4(2) . . ?
C1A C6A C7 110.3(2) . . ?
C5A C6A C7 132.3(2) . . ?
N1 C13A C14A 113.52(19) . . ?
N1 C13A C5A 107.19(19) . . ?
C14A C13A C5A 116.05(19) . . ?
N1 C13A H13A 106.5 . . ?
C14A C13A H13A 106.5 . . ?
C5A C13A H13A 106.5 . . ?
C13A C14A C15A 112.94(18) . . ?
C13A C14A H14A 109.0 . . ?
C15A C14A H14A 109.0 . . ?
C13A C14A H14B 109.0 . . ?
C15A C14A H14B 109.0 . . ?
H14A C14A H14B 107.8 . . ?
C14A C15A H15A 109.5 . . ?
C14A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
C14A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C12 S1B C1B 81.6(5) . . ?
C6B C1B C2B 120.7(13) . . ?
C6B C1B S1B 117.8(10) . . ?
C2B C1B S1B 121.5(11) . . ?
C3B C2B C1B 116.8(14) . . ?
C3B C2B H2B 121.6 . . ?
C1B C2B H2B 121.6 . . ?
C2B C3B C4B 123.3(14) . . ?
C2B C3B H3B 118.4 . . ?
C4B C3B H3B 118.4 . . ?
C3B C4B C5B 119.4(14) . . ?
C3B C4B H4B 120.3 . . ?
C5B C4B H4B 120.3 . . ?
C6B C5B C4B 115.8(13) . . ?
C6B C5B C13B 124.8(13) . . ?
C4B C5B C13B 119.4(13) . . ?
C5B C6B C1B 123.8(13) . . ?
C5B C6B C7 122.2(12) . . ?
C1B C6B C7 114.0(12) . . ?
C5B C13B C14B 109.6(11) . . ?
C5B C13B N1 116.8(10) . . ?
C14B C13B N1 117.3(10) . . ?
C5B C13B H13B 103.7 . . ?
C14B C13B H13B 103.7 . . ?
N1 C13B H13B 103.7 . . ?
C15B C14B C13B 111.8(12) . . ?
C15B C14B H14C 109.2 . . ?
C13B C14B H14C 109.2 . . ?
C15B C14B H14D 109.2 . . ?
C13B C14B H14D 109.2 . . ?
H14C C14B H14D 107.9 . . ?
C14B C15B H15D 109.5 . . ?
C14B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C14B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
C8 C7 C12 117.3(2) . . ?
C8 C7 C6B 144.4(7) . . ?
C12 C7 C6B 98.1(7) . . ?
C8 C7 C6A 129.2(2) . . ?
C12 C7 C6A 113.5(2) . . ?
C9 C8 C7 120.3(2) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 121.3(2) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C11 C10 C9 119.9(2) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 119.0(2) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C11 C12 C7 122.2(2) . . ?
C11 C12 S1B 109.2(3) . . ?
C7 C12 S1B 128.1(3) . . ?
C11 C12 S1A 127.03(19) . . ?
C7 C12 S1A 110.76(19) . . ?
C18B C16 C17B 118.8(3) . . ?
C19A C16 C17A 110.9(3) . . ?
C18B C16 C19B 112.8(3) . . ?
C17B C16 C19B 109.6(3) . . ?
C19A C16 C18A 108.4(3) . . ?
C17A C16 C18A 105.1(3) . . ?
C18B C16 S2 114.2(2) . . ?
C17B C16 S2 103.4(2) . . ?
C19A C16 S2 115.2(2) . . ?
C17A C16 S2 108.7(2) . . ?
C19B C16 S2 95.29(19) . . ?
C18A C16 S2 108.10(17) . . ?
C16 C17A H17A 109.5 . . ?
C16 C17A H17B 109.5 . . ?
H17A C17A H17B 109.5 . . ?
C16 C17A H17C 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
C16 C18A H18A 109.5 . . ?
C16 C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C16 C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C16 C19A H19A 109.5 . . ?
C16 C19A H19B 109.5 . . ?
H19A C19A H19B 109.5 . . ?
C16 C19A H19C 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
C16 C17B H17D 109.5 . . ?
C16 C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
C16 C17B H17F 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
C16 C18B H18D 109.5 . . ?
C16 C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
C16 C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
C16 C19B H19D 109.5 . . ?
C16 C19B H19E 109.5 . . ?
H19D C19B H19E 109.5 . . ?
C16 C19B H19F 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 S2 O1A O1B -157.2(7) . . . . ?
C16 S2 O1A O1B 100.8(7) . . . . ?
N1 S2 O1B O1A 26.6(8) . . . . ?
C16 S2 O1B O1A -85.2(7) . . . . ?
O1B S2 N1 C13A 79.2(2) . . . . ?
O1A S2 N1 C13A 89.0(2) . . . . ?
C16 S2 N1 C13A -164.68(16) . . . . ?
O1B S2 N1 C13B 94.1(5) . . . . ?
O1A S2 N1 C13B 103.8(5) . . . . ?
C16 S2 N1 C13B -149.9(5) . . . . ?
C12 S1A C1A C2A 179.6(2) . . . . ?
C12 S1A C1A C6A -0.5(2) . . . . ?
C6A C1A C2A C3A -1.3(4) . . . . ?
S1A C1A C2A C3A 178.5(2) . . . . ?
C1A C2A C3A C4A -1.5(4) . . . . ?
C2A C3A C4A C5A 1.8(4) . . . . ?
C3A C4A C5A C6A 0.7(4) . . . . ?
C3A C4A C5A C13A 179.5(2) . . . . ?
C2A C1A C6A C5A 3.7(4) . . . . ?
S1A C1A C6A C5A -176.1(2) . . . . ?
C2A C1A C6A C7 -178.7(2) . . . . ?
S1A C1A C6A C7 1.4(3) . . . . ?
C4A C5A C6A C1A -3.3(4) . . . . ?
C13A C5A C6A C1A 177.9(2) . . . . ?
C4A C5A C6A C7 179.8(3) . . . . ?
C13A C5A C6A C7 1.0(5) . . . . ?
S2 N1 C13A C14A -65.6(2) . . . . ?
S2 N1 C13A C5A 63.8(2) . . . . ?
C4A C5A C13A N1 -103.3(2) . . . . ?
C6A C5A C13A N1 75.5(3) . . . . ?
C4A C5A C13A C14A 24.7(3) . . . . ?
C6A C5A C13A C14A -156.5(2) . . . . ?
N1 C13A C14A C15A -167.48(18) . . . . ?
C5A C13A C14A C15A 67.7(3) . . . . ?
C12 S1B C1B C6B 0.9(16) . . . . ?
C12 S1B C1B C2B -177.6(15) . . . . ?
C6B C1B C2B C3B 2(3) . . . . ?
S1B C1B C2B C3B -179.7(14) . . . . ?
C1B C2B C3B C4B -4(3) . . . . ?
C2B C3B C4B C5B 4(3) . . . . ?
C3B C4B C5B C6B -2(3) . . . . ?
C3B C4B C5B C13B 179.1(15) . . . . ?
C4B C5B C6B C1B -1(3) . . . . ?
C13B C5B C6B C1B 178.6(18) . . . . ?
C4B C5B C6B C7 178.5(16) . . . . ?
C13B C5B C6B C7 -2(3) . . . . ?
C2B C1B C6B C5B 1(3) . . . . ?
S1B C1B C6B C5B -178.0(18) . . . . ?
C2B C1B C6B C7 -178.6(16) . . . . ?
S1B C1B C6B C7 3(2) . . . . ?
C6B C5B C13B C14B -151.0(19) . . . . ?
C4B C5B C13B C14B 28(2) . . . . ?
C6B C5B C13B N1 73(2) . . . . ?
C4B C5B C13B N1 -108.4(15) . . . . ?
S2 N1 C13B C5B 67.8(11) . . . . ?
S2 N1 C13B C14B -65.2(11) . . . . ?
C5B C13B C14B C15B 164.3(14) . . . . ?
N1 C13B C14B C15B -59.5(17) . . . . ?
C5B C6B C7 C8 -9(3) . . . . ?
C1B C6B C7 C8 169.8(9) . . . . ?
C5B C6B C7 C12 175.5(19) . . . . ?
C1B C6B C7 C12 -5.3(19) . . . . ?
C1A C6A C7 C8 179.1(2) . . . . ?
C5A C6A C7 C8 -3.8(5) . . . . ?
C1A C6A C7 C12 -2.0(3) . . . . ?
C5A C6A C7 C12 175.1(3) . . . . ?
C12 C7 C8 C9 -2.3(3) . . . . ?
C6B C7 C8 C9 -176.9(17) . . . . ?
C6A C7 C8 C9 176.6(2) . . . . ?
C7 C8 C9 C10 1.0(3) . . . . ?
C8 C9 C10 C11 0.8(4) . . . . ?
C9 C10 C11 C12 -1.1(3) . . . . ?
C10 C11 C12 C7 -0.4(3) . . . . ?
C10 C11 C12 S1B 172.6(3) . . . . ?
C10 C11 C12 S1A -178.78(18) . . . . ?
C8 C7 C12 C11 2.1(3) . . . . ?
C6B C7 C12 C11 178.9(10) . . . . ?
C6A C7 C12 C11 -177.0(2) . . . . ?
C8 C7 C12 S1B -169.5(3) . . . . ?
C6B C7 C12 S1B 7.3(11) . . . . ?
C8 C7 C12 S1A -179.27(15) . . . . ?
C6A C7 C12 S1A 1.6(2) . . . . ?
C1B S1B C12 C11 -177.8(6) . . . . ?
C1B S1B C12 C7 -5.4(7) . . . . ?
C1A S1A C12 C11 177.9(2) . . . . ?
C1A S1A C12 C7 -0.69(18) . . . . ?
O1B S2 C16 C18B 97.0(3) . . . . ?
O1A S2 C16 C18B 74.7(3) . . . . ?
N1 S2 C16 C18B -30.5(3) . . . . ?
O1B S2 C16 C17B -33.5(3) . . . . ?
O1A S2 C16 C17B -55.8(3) . . . . ?
N1 S2 C16 C17B -160.9(2) . . . . ?
O1B S2 C16 C19A 177.5(3) . . . . ?
O1A S2 C16 C19A 155.2(3) . . . . ?
N1 S2 C16 C19A 50.1(2) . . . . ?
O1B S2 C16 C17A -57.4(3) . . . . ?
O1A S2 C16 C17A -79.7(3) . . . . ?
N1 S2 C16 C17A 175.1(2) . . . . ?
O1B S2 C16 C19B -145.1(2) . . . . ?
O1A S2 C16 C19B -167.3(2) . . . . ?
N1 S2 C16 C19B 87.50(17) . . . . ?
O1B S2 C16 C18A 56.1(2) . . . . ?
O1A S2 C16 C18A 33.8(2) . . . . ?
N1 S2 C16 C18A -71.33(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O1A 0.91(3) 2.19(3) 2.886(4) 133(2) 3_655 yes
N1 H1 O1B 0.91(3) 2.06(3) 2.849(4) 145(3) 3_655 yes

_refine_diff_density_max         0.422
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_compound3k_AS030B
_database_code_depnum_ccdc_archive 'CCDC 2060190'
loop_
_audit_author_name
_audit_author_address
'Katherine Robertson' 'Saint Marys University'
_audit_update_record             
;
2021-01-31 deposited with the CCDC.	2021-02-09 downloaded from the CCDC.
;

#==============================================================================

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 O S'
_chemical_formula_sum            'C15 H12 O S'
_chemical_formula_weight         240.31

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   6.0539(8)
_cell_length_b                   21.767(3)
_cell_length_c                   8.6784(12)
_cell_angle_alpha                90
_cell_angle_beta                 97.314(5)
_cell_angle_gamma                90
_cell_volume                     1134.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    9674
_cell_measurement_theta_min      2.5445
_cell_measurement_theta_max      39.2018

_exptl_crystal_description       'diamond shaped plate'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.278
_exptl_crystal_size_mid          0.245
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.263
_shelx_estimated_absorpt_T_min   0.931
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6551
_exptl_absorpt_correction_T_max  0.7479
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_source            'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device       'κ--geometry diffractometer'
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

_diffrn_reflns_number            85596
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.544
_diffrn_reflns_theta_max         36.318
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5501
_reflns_number_gt                4412
_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       'Bruker Instrument Service vV6.2.14 Patch 4'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (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)+(0.0408P)²+0.5905P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'Intrinsic Phasing'
_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         5501
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1146
_refine_ls_wR_factor_gt          0.1068
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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 -0.06193(4) 0.28185(2) 0.74189(3) 0.02132(7) Uani 1 1 d . . . . .
O1 O 0.69302(15) 0.39270(4) 0.38965(11) 0.02758(18) Uani 1 1 d . . . . .
C1 C 0.09294(18) 0.34147(5) 0.67652(12) 0.01950(18) Uani 1 1 d . . . . .
C2 C 0.0457(2) 0.40347(6) 0.69540(14) 0.0244(2) Uani 1 1 d . . . . .
H2 H -0.074595 0.415646 0.748965 0.029 Uiso 1 1 calc R U . . .
C3 C 0.1768(2) 0.44685(6) 0.63486(15) 0.0273(2) Uani 1 1 d . . . . .
H3 H 0.149116 0.489375 0.647902 0.033 Uiso 1 1 calc R U . . .
C4 C 0.3496(2) 0.42796(6) 0.55460(14) 0.0263(2) Uani 1 1 d . . . . .
H4 H 0.437953 0.458279 0.512755 0.032 Uiso 1 1 calc R U . . .
C5 C 0.39789(19) 0.36627(5) 0.53341(13) 0.02032(19) Uani 1 1 d . . . . .
C6 C 0.27042(17) 0.32076(5) 0.59782(12) 0.01735(17) Uani 1 1 d . . . . .
C7 C 0.28233(16) 0.25397(5) 0.59718(12) 0.01682(17) Uani 1 1 d . . . . .
C8 C 0.43243(17) 0.21346(5) 0.53850(12) 0.01822(17) Uani 1 1 d . . . . .
H8 H 0.553012 0.229809 0.491406 0.022 Uiso 1 1 calc R U . . .
C9 C 0.40857(17) 0.15029(5) 0.54778(12) 0.01893(18) Uani 1 1 d . . . . .
C10 C 0.23174(18) 0.12543(5) 0.62019(13) 0.01989(18) Uani 1 1 d . . . . .
C11 C 0.08521(18) 0.16434(5) 0.68264(13) 0.02074(19) Uani 1 1 d . . . . .
H11 H -0.031722 0.147945 0.733463 0.025 Uiso 1 1 calc R U . . .
C12 C 0.11068(17) 0.22764(5) 0.67031(12) 0.01819(17) Uani 1 1 d . . . . .
C13 C 0.57098(19) 0.35337(6) 0.43091(13) 0.0226(2) Uani 1 1 d . . . . .
H13 H 0.586970 0.312439 0.395994 0.027 Uiso 1 1 calc R U . . .
C14 C 0.5722(2) 0.10863(6) 0.48311(15) 0.0247(2) Uani 1 1 d . . . . .
H14A H 0.687844 0.133393 0.443457 0.037 Uiso 1 1 calc R U . . .
H14B H 0.494497 0.084027 0.398401 0.037 Uiso 1 1 calc R U . . .
H14C H 0.640967 0.081300 0.565316 0.037 Uiso 1 1 calc R U . . .
C15 C 0.2059(2) 0.05685(6) 0.63282(16) 0.0278(2) Uani 1 1 d . . . . .
H15A H 0.074224 0.047646 0.683742 0.042 Uiso 1 1 calc R U . . .
H15B H 0.338485 0.039619 0.694269 0.042 Uiso 1 1 calc R U . . .
H15C H 0.188135 0.038664 0.528675 0.042 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 C1 1.7379(11) . ?
S1 C12 1.7423(11) . ?
O1 C13 1.2141(13) . ?
C1 C2 1.3936(16) . ?
C1 C6 1.4181(14) . ?
C2 C3 1.3797(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.3911(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3915(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.4139(14) . ?
C5 C13 1.4851(15) . ?
C6 C7 1.4556(15) . ?
C7 C12 1.4067(14) . ?
C7 C8 1.4072(14) . ?
C8 C9 1.3861(15) . ?
C8 H8 0.9500 . ?
C9 C10 1.4160(14) . ?
C9 C14 1.5035(16) . ?
C10 C11 1.3858(16) . ?
C10 C15 1.5064(16) . ?
C11 C12 1.3921(15) . ?
C11 H11 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C12 90.94(5) . . ?
C2 C1 C6 122.96(10) . . ?
C2 C1 S1 123.87(8) . . ?
C6 C1 S1 113.15(8) . . ?
C3 C2 C1 118.76(11) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 119.63(11) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 122.36(11) . . ?
C3 C4 H4 118.8 . . ?
C5 C4 H4 118.8 . . ?
C4 C5 C6 119.32(10) . . ?
C4 C5 C13 115.95(10) . . ?
C6 C5 C13 124.51(10) . . ?
C5 C6 C1 116.92(10) . . ?
C5 C6 C7 131.95(9) . . ?
C1 C6 C7 111.12(9) . . ?
C12 C7 C8 117.14(9) . . ?
C12 C7 C6 111.43(9) . . ?
C8 C7 C6 131.43(9) . . ?
C9 C8 C7 121.58(9) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C10 119.68(10) . . ?
C8 C9 C14 119.88(9) . . ?
C10 C9 C14 120.43(10) . . ?
C11 C10 C9 119.85(10) . . ?
C11 C10 C15 119.97(10) . . ?
C9 C10 C15 120.16(10) . . ?
C10 C11 C12 119.49(9) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C11 C12 C7 122.23(10) . . ?
C11 C12 S1 124.45(8) . . ?
C7 C12 S1 113.33(8) . . ?
O1 C13 C5 123.07(11) . . ?
O1 C13 H13 118.5 . . ?
C5 C13 H13 118.5 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 S1 C1 C2 179.92(11) . . . . ?
C12 S1 C1 C6 1.45(9) . . . . ?
C6 C1 C2 C3 0.08(18) . . . . ?
S1 C1 C2 C3 -178.24(10) . . . . ?
C1 C2 C3 C4 1.07(19) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C3 C4 C5 C6 -1.25(19) . . . . ?
C3 C4 C5 C13 173.59(12) . . . . ?
C4 C5 C6 C1 2.29(16) . . . . ?
C13 C5 C6 C1 -172.08(10) . . . . ?
C4 C5 C6 C7 -179.12(11) . . . . ?
C13 C5 C6 C7 6.52(19) . . . . ?
C2 C1 C6 C5 -1.77(16) . . . . ?
S1 C1 C6 C5 176.72(8) . . . . ?
C2 C1 C6 C7 179.35(11) . . . . ?
S1 C1 C6 C7 -2.16(12) . . . . ?
C5 C6 C7 C12 -176.78(11) . . . . ?
C1 C6 C7 C12 1.88(13) . . . . ?
C5 C6 C7 C8 3.7(2) . . . . ?
C1 C6 C7 C8 -177.68(11) . . . . ?
C12 C7 C8 C9 1.99(16) . . . . ?
C6 C7 C8 C9 -178.48(11) . . . . ?
C7 C8 C9 C10 -1.11(16) . . . . ?
C7 C8 C9 C14 179.78(10) . . . . ?
C8 C9 C10 C11 -0.65(16) . . . . ?
C14 C9 C10 C11 178.45(11) . . . . ?
C8 C9 C10 C15 -179.20(11) . . . . ?
C14 C9 C10 C15 -0.10(17) . . . . ?
C9 C10 C11 C12 1.44(17) . . . . ?
C15 C10 C11 C12 179.99(11) . . . . ?
C10 C11 C12 C7 -0.51(17) . . . . ?
C10 C11 C12 S1 179.50(9) . . . . ?
C8 C7 C12 C11 -1.18(16) . . . . ?
C6 C7 C12 C11 179.20(10) . . . . ?
C8 C7 C12 S1 178.81(8) . . . . ?
C6 C7 C12 S1 -0.82(12) . . . . ?
C1 S1 C12 C11 179.65(10) . . . . ?
C1 S1 C12 C7 -0.34(9) . . . . ?
C4 C5 C13 O1 12.95(18) . . . . ?
C6 C5 C13 O1 -172.51(12) . . . . ?

_refine_diff_density_max         0.435
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_compound3f_AS029
_database_code_depnum_ccdc_archive 'CCDC 2060191'
loop_
_audit_author_name
_audit_author_address
'Katherine Robertson' 'Saint Marys University'
_audit_update_record             
;
2021-01-31 deposited with the CCDC.	2021-02-09 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         'C13 H7 N S'
_chemical_formula_sum            'C13 H7 N S'
_chemical_formula_weight         209.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   7.6092(14)
_cell_length_b                   3.8618(7)
_cell_length_c                   32.437(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.374(8)
_cell_angle_gamma                90
_cell_volume                     947.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    9289
_cell_measurement_theta_min      2.5273
_cell_measurement_theta_max      36.2043

_exptl_crystal_description       'rectangular prism'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.436
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.298
_shelx_estimated_absorpt_T_min   0.881
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.6497
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_source            'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device       'κ--geometry diffractometer'
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            76115
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_theta_min         2.527
_diffrn_reflns_theta_max         34.336
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3958
_reflns_number_gt                3620
_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       
;
Bruker Instrument Service, BIS, v.6.2.10 (Bruker AXS Inc., 2018)
;
_computing_cell_refinement       'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_data_reduction        'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_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)+(0.0408P)²+0.7548P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'dual space'
_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         3958
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1159
_refine_ls_wR_factor_gt          0.1131
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_restrained_S_all      1.126
_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 0.31100(4) 0.78219(8) 0.17741(2) 0.01929(8) Uani 1 1 d . . . . .
N1 N 0.6966(2) 0.0765(4) 0.04471(4) 0.0379(3) Uani 1 1 d . . . . .
C1 C 0.28176(17) 0.6517(3) 0.12567(4) 0.0206(2) Uani 1 1 d . . . . .
C2 C 0.12613(19) 0.6900(4) 0.09909(4) 0.0263(2) Uani 1 1 d . . . . .
H2 H 0.024586 0.793686 0.108482 0.032 Uiso 1 1 calc R U . . .
C3 C 0.1230(2) 0.5730(5) 0.05854(4) 0.0316(3) Uani 1 1 d . . . . .
H3 H 0.018516 0.599477 0.039864 0.038 Uiso 1 1 calc R U . . .
C4 C 0.2717(2) 0.4166(4) 0.04490(4) 0.0307(3) Uani 1 1 d . . . . .
H4 H 0.267047 0.335209 0.017159 0.037 Uiso 1 1 calc R U . . .
C5 C 0.42650(19) 0.3795(4) 0.07164(4) 0.0250(2) Uani 1 1 d . . . . .
C6 C 0.43520(17) 0.4993(3) 0.11294(4) 0.0205(2) Uani 1 1 d . . . . .
C7 C 0.57991(16) 0.4928(3) 0.14606(4) 0.0199(2) Uani 1 1 d . . . . .
C8 C 0.75327(18) 0.3669(4) 0.14644(4) 0.0241(2) Uani 1 1 d . . . . .
H8 H 0.790831 0.267931 0.122071 0.029 Uiso 1 1 calc R U . . .
C9 C 0.86920(18) 0.3873(4) 0.18235(5) 0.0258(2) Uani 1 1 d . . . . .
H9 H 0.986419 0.302459 0.182406 0.031 Uiso 1 1 calc R U . . .
C10 C 0.81636(17) 0.5309(4) 0.21859(4) 0.0251(2) Uani 1 1 d . . . . .
H10 H 0.897583 0.540608 0.243014 0.030 Uiso 1 1 calc R U . . .
C11 C 0.64666(17) 0.6592(3) 0.21917(4) 0.0218(2) Uani 1 1 d . . . . .
H11 H 0.610623 0.758711 0.243669 0.026 Uiso 1 1 calc R U . . .
C12 C 0.52952(16) 0.6386(3) 0.18277(4) 0.0188(2) Uani 1 1 d . . . . .
C13 C 0.5774(2) 0.2133(4) 0.05665(4) 0.0288(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.7428(13) . ?
S1 C12 1.7431(13) . ?
N1 C13 1.153(2) . ?
C1 C2 1.3932(19) . ?
C1 C6 1.4097(17) . ?
C2 C3 1.388(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.397(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.4119(17) . ?
C5 C13 1.446(2) . ?
C6 C7 1.4507(18) . ?
C7 C8 1.4047(18) . ?
C7 C12 1.4084(17) . ?
C8 C9 1.383(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.398(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.3852(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.4004(18) . ?
C11 H11 0.9500 . ?

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 C12 91.29(6) . . ?
C2 C1 C6 122.53(12) . . ?
C2 C1 S1 125.04(10) . . ?
C6 C1 S1 112.43(9) . . ?
C3 C2 C1 118.41(14) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 120.75(14) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 120.44(13) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.36(13) . . ?
C4 C5 C13 119.03(13) . . ?
C6 C5 C13 120.61(13) . . ?
C1 C6 C5 117.49(12) . . ?
C1 C6 C7 112.05(10) . . ?
C5 C6 C7 130.46(12) . . ?
C8 C7 C12 118.33(12) . . ?
C8 C7 C6 130.33(11) . . ?
C12 C7 C6 111.33(11) . . ?
C9 C8 C7 119.87(12) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 120.96(12) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C11 C10 C9 120.59(13) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 118.37(12) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
C11 C12 C7 121.87(11) . . ?
C11 C12 S1 125.23(9) . . ?
C7 C12 S1 112.90(9) . . ?
N1 C13 C5 179.09(17) . . ?

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
C12 S1 C1 C2 -179.50(12) . . . . ?
C12 S1 C1 C6 0.49(10) . . . . ?
C6 C1 C2 C3 0.0(2) . . . . ?
S1 C1 C2 C3 179.99(11) . . . . ?
C1 C2 C3 C4 0.8(2) . . . . ?
C2 C3 C4 C5 -0.8(2) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C3 C4 C5 C13 179.35(14) . . . . ?
C2 C1 C6 C5 -0.74(19) . . . . ?
S1 C1 C6 C5 179.27(10) . . . . ?
C2 C1 C6 C7 179.35(12) . . . . ?
S1 C1 C6 C7 -0.64(14) . . . . ?
C4 C5 C6 C1 0.72(19) . . . . ?
C13 C5 C6 C1 -178.60(12) . . . . ?
C4 C5 C6 C7 -179.39(13) . . . . ?
C13 C5 C6 C7 1.3(2) . . . . ?
C1 C6 C7 C8 -179.74(13) . . . . ?
C5 C6 C7 C8 0.4(2) . . . . ?
C1 C6 C7 C12 0.49(15) . . . . ?
C5 C6 C7 C12 -179.41(13) . . . . ?
C12 C7 C8 C9 0.20(19) . . . . ?
C6 C7 C8 C9 -179.56(13) . . . . ?
C7 C8 C9 C10 0.2(2) . . . . ?
C8 C9 C10 C11 -0.6(2) . . . . ?
C9 C10 C11 C12 0.5(2) . . . . ?
C10 C11 C12 C7 -0.10(19) . . . . ?
C10 C11 C12 S1 179.52(10) . . . . ?
C8 C7 C12 C11 -0.26(18) . . . . ?
C6 C7 C12 C11 179.54(11) . . . . ?
C8 C7 C12 S1 -179.92(10) . . . . ?
C6 C7 C12 S1 -0.12(13) . . . . ?
C1 S1 C12 C11 -179.86(11) . . . . ?
C1 S1 C12 C7 -0.21(10) . . . . ?

_refine_diff_density_max         0.701
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.078

####################################################################### 
# 
# 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_compound3g_AS031B
_database_code_depnum_ccdc_archive 'CCDC 2060192'
loop_
_audit_author_name
_audit_author_address
'Katherine Robertson' 'Saint Marys University'
_audit_update_record             
;
2021-01-31 deposited with the CCDC.	2021-02-09 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         '4(C14 H7 F3 O1 S1)'
_chemical_formula_sum            'C56 H28 F12 O4 S4'
_chemical_formula_weight         1121.02

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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'
'-x, -y, -z'

_cell_length_a                   8.2143(4)
_cell_length_b                   8.2225(5)
_cell_length_c                   35.165(2)
_cell_angle_alpha                89.531(2)
_cell_angle_beta                 89.289(2)
_cell_angle_gamma                78.488(2)
_cell_volume                     2327.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    9966
_cell_measurement_theta_min      2.3169
_cell_measurement_theta_max      38.6085

_exptl_crystal_description       chip
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_F_000             1136
_exptl_transmission_factor_min   0.6953
_exptl_transmission_factor_max   0.7479
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.063
_exptl_absorpt_coefficient_mu    0.304
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_source            'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device       'κ--geometry diffractometer'
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            227991
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -58
_diffrn_reflns_limit_l_max       58
_diffrn_reflns_theta_min         2.317
_diffrn_reflns_theta_max         36.318
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             22572
_reflns_number_gt                17356
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Bruker Instrument Service vV6.2.14 Patch 4'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0618P)²+1.0339P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'intrinsic phasing'
_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         22572
_refine_ls_number_parameters     686
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1373
_refine_ls_wR_factor_gt          0.1223
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.41180(5) 0.82848(4) 0.31976(2) 0.02521(7) Uani 1 1 d . . . . .
S2 S 0.88067(5) -0.34583(5) 0.31606(2) 0.02976(8) Uani 1 1 d . . . . .
S3 S -0.32539(4) 0.57308(5) 0.18098(2) 0.02534(7) Uani 1 1 d . . . . .
S4 S 0.84053(5) 0.10454(5) 0.18538(2) 0.02940(8) Uani 1 1 d . . . . .
F1 F 0.28786(18) 0.20344(13) 0.45559(4) 0.0461(3) Uani 1 1 d . . . . .
F2 F 0.3529(2) 0.43089(15) 0.47211(3) 0.0516(3) Uani 1 1 d . . . . .
F3 F 0.1020(2) 0.4025(2) 0.47747(4) 0.0724(5) Uani 1 1 d . . . . .
F4 F 0.86170(15) -0.01224(18) 0.47960(3) 0.0455(3) Uani 1 1 d . . . . .
F5 F 0.61127(16) 0.1052(2) 0.48839(3) 0.0561(4) Uani 1 1 d . . . . .
F6 F 0.7867(3) 0.2489(2) 0.46973(4) 0.0841(6) Uani 1 1 d . . . . .
F7 F 0.29069(13) 0.70859(17) 0.04372(3) 0.0442(3) Uani 1 1 d . . . . .
F8 F 0.06471(15) 0.63589(19) 0.02867(3) 0.0504(3) Uani 1 1 d . . . . .
F9 F 0.0857(2) 0.8895(2) 0.02246(4) 0.0670(4) Uani 1 1 d . . . . .
F10 F 0.51995(18) 0.13541(16) 0.02075(3) 0.0491(3) Uani 1 1 d . . . . .
F11 F 0.4012(2) 0.38442(18) 0.01109(3) 0.0624(4) Uani 1 1 d . . . . .
F12 F 0.2584(2) 0.2089(3) 0.03033(5) 0.0959(8) Uani 1 1 d . . . . .
O1 O 0.13938(16) 0.34026(14) 0.39349(3) 0.0314(2) Uani 1 1 d . . . . .
O2 O 0.6441(2) 0.20081(15) 0.40534(4) 0.0397(3) Uani 1 1 d . . . . .
O3 O 0.15812(15) 0.85208(17) 0.10619(3) 0.0338(2) Uani 1 1 d . . . . .
O4 O 0.30612(16) 0.3609(2) 0.09381(4) 0.0407(3) Uani 1 1 d . . . . .
C1 C 0.31438(17) 0.79849(16) 0.36246(4) 0.0220(2) Uani 1 1 d . . . . .
C2 C 0.25851(19) 0.92547(17) 0.38839(4) 0.0266(3) Uani 1 1 d . . . . .
H2 H 0.269123 1.036219 0.382896 0.032 Uiso 1 1 calc R U . . .
C3 C 0.1876(2) 0.88688(18) 0.42212(4) 0.0283(3) Uani 1 1 d . . . . .
H3 H 0.147312 0.971956 0.439968 0.034 Uiso 1 1 calc R U . . .
C4 C 0.17471(19) 0.72336(18) 0.43022(4) 0.0263(2) Uani 1 1 d . . . . .
H4 H 0.128921 0.697896 0.453950 0.032 Uiso 1 1 calc R U . . .
C5 C 0.22792(17) 0.59681(16) 0.40404(4) 0.0219(2) Uani 1 1 d . . . . .
C6 C 0.29989(16) 0.63209(15) 0.36905(4) 0.0200(2) Uani 1 1 d . . . . .
C7 C 0.37549(16) 0.52578(15) 0.33800(3) 0.0200(2) Uani 1 1 d . . . . .
C8 C 0.39963(19) 0.35272(17) 0.33317(4) 0.0258(2) Uani 1 1 d . . . . .
H8 H 0.358853 0.286248 0.351812 0.031 Uiso 1 1 calc R U . . .
C9 C 0.4826(2) 0.27965(18) 0.30133(4) 0.0291(3) Uani 1 1 d . . . . .
H9 H 0.499061 0.162748 0.298357 0.035 Uiso 1 1 calc R U . . .
C10 C 0.54282(19) 0.37537(19) 0.27335(4) 0.0277(3) Uani 1 1 d . . . . .
H10 H 0.598154 0.323145 0.251455 0.033 Uiso 1 1 calc R U . . .
C11 C 0.52227(19) 0.54484(18) 0.27740(4) 0.0253(2) Uani 1 1 d . . . . .
H11 H 0.563583 0.610157 0.258590 0.030 Uiso 1 1 calc R U . . .
C12 C 0.43978(17) 0.61826(16) 0.30961(4) 0.0217(2) Uani 1 1 d . . . . .
C13 C 0.19602(18) 0.43065(17) 0.41424(4) 0.0239(2) Uani 1 1 d . . . . .
C14 C 0.2357(2) 0.3665(2) 0.45551(4) 0.0327(3) Uani 1 1 d . . . . .
C15 C 0.79986(18) -0.30430(18) 0.36144(4) 0.0262(2) Uani 1 1 d . . . . .
C16 C 0.7417(2) -0.42031(19) 0.38438(5) 0.0319(3) Uani 1 1 d . . . . .
H16 H 0.742837 -0.529079 0.375333 0.038 Uiso 1 1 calc R U . . .
C17 C 0.6825(2) -0.3744(2) 0.42044(5) 0.0346(3) Uani 1 1 d . . . . .
H17 H 0.644242 -0.452214 0.436628 0.041 Uiso 1 1 calc R U . . .
C18 C 0.6792(2) -0.2134(2) 0.43299(5) 0.0303(3) Uani 1 1 d . . . . .
H18 H 0.640477 -0.183600 0.458032 0.036 Uiso 1 1 calc R U . . .
C19 C 0.73154(18) -0.09451(18) 0.40965(4) 0.0251(2) Uani 1 1 d . . . . .
C20 C 0.79687(17) -0.13938(17) 0.37299(4) 0.0231(2) Uani 1 1 d . . . . .
C21 C 0.86968(17) -0.04746(17) 0.34368(4) 0.0226(2) Uani 1 1 d . . . . .
C22 C 0.9072(2) 0.11198(18) 0.34408(4) 0.0271(3) Uani 1 1 d . . . . .
H22 H 0.880686 0.179731 0.365934 0.033 Uiso 1 1 calc R U . . .
C23 C 0.9823(2) 0.1710(2) 0.31290(5) 0.0307(3) Uani 1 1 d . . . . .
H23 H 1.007942 0.278576 0.313593 0.037 Uiso 1 1 calc R U . . .
C24 C 1.0211(2) 0.0734(2) 0.28026(5) 0.0308(3) Uani 1 1 d . . . . .
H24 H 1.069362 0.116780 0.258734 0.037 Uiso 1 1 calc R U . . .
C25 C 0.9896(2) -0.0852(2) 0.27918(4) 0.0294(3) Uani 1 1 d . . . . .
H25 H 1.016771 -0.152196 0.257236 0.035 Uiso 1 1 calc R U . . .
C26 C 0.91660(18) -0.14492(18) 0.31115(4) 0.0249(2) Uani 1 1 d . . . . .
C27 C 0.7011(2) 0.07795(19) 0.42367(4) 0.0274(3) Uani 1 1 d . . . . .
C28 C 0.7420(2) 0.1061(2) 0.46582(5) 0.0342(3) Uani 1 1 d . . . . .
C29 C -0.29769(16) 0.67186(18) 0.13819(4) 0.0226(2) Uani 1 1 d . . . . .
C30 C -0.42505(17) 0.7254(2) 0.11229(4) 0.0280(3) Uani 1 1 d . . . . .
H30 H -0.535144 0.712166 0.117850 0.034 Uiso 1 1 calc R U . . .
C31 C -0.38882(18) 0.7978(2) 0.07856(5) 0.0301(3) Uani 1 1 d . . . . .
H31 H -0.474495 0.836908 0.060882 0.036 Uiso 1 1 calc R U . . .
C32 C -0.22630(18) 0.8133(2) 0.07048(4) 0.0279(3) Uani 1 1 d . . . . .
H32 H -0.201414 0.859124 0.046737 0.034 Uiso 1 1 calc R U . . .
C33 C -0.09891(16) 0.76278(18) 0.09660(4) 0.0233(2) Uani 1 1 d . . . . .
C34 C -0.13251(15) 0.69047(17) 0.13191(4) 0.0212(2) Uani 1 1 d . . . . .
C35 C -0.02620(16) 0.61994(17) 0.16349(4) 0.0217(2) Uani 1 1 d . . . . .
C36 C 0.14464(18) 0.6049(2) 0.16925(4) 0.0306(3) Uani 1 1 d . . . . .
H36 H 0.210586 0.647115 0.150679 0.037 Uiso 1 1 calc R U . . .
C37 C 0.2182(2) 0.5290(3) 0.20184(5) 0.0355(3) Uani 1 1 d . . . . .
H37 H 0.334456 0.518849 0.205111 0.043 Uiso 1 1 calc R U . . .
C38 C 0.1250(2) 0.4673(2) 0.22994(4) 0.0312(3) Uani 1 1 d . . . . .
H38 H 0.177157 0.418082 0.252362 0.037 Uiso 1 1 calc R U . . .
C39 C -0.04346(19) 0.47794(19) 0.22501(4) 0.0262(2) Uani 1 1 d . . . . .
H39 H -0.108192 0.434730 0.243672 0.031 Uiso 1 1 calc R U . . .
C40 C -0.11658(16) 0.55368(17) 0.19198(4) 0.0221(2) Uani 1 1 d . . . . .
C41 C 0.06615(17) 0.79524(19) 0.08599(4) 0.0245(2) Uani 1 1 d . . . . .
C42 C 0.1271(2) 0.7561(2) 0.04456(4) 0.0324(3) Uani 1 1 d . . . . .
C43 C 0.80487(18) 0.18859(18) 0.13991(4) 0.0262(2) Uani 1 1 d . . . . .
C44 C 0.92415(19) 0.2469(2) 0.11792(5) 0.0327(3) Uani 1 1 d . . . . .
H44 H 1.032282 0.244187 0.127502 0.039 Uiso 1 1 calc R U . . .
C45 C 0.8816(2) 0.3087(2) 0.08185(5) 0.0350(3) Uani 1 1 d . . . . .
H45 H 0.961826 0.346746 0.066300 0.042 Uiso 1 1 calc R U . . .
C46 C 0.7216(2) 0.3153(2) 0.06820(5) 0.0315(3) Uani 1 1 d . . . . .
H46 H 0.694941 0.355822 0.043205 0.038 Uiso 1 1 calc R U . . .
C47 C 0.60040(18) 0.26353(19) 0.09066(4) 0.0252(2) Uani 1 1 d . . . . .
C48 C 0.64109(16) 0.19469(17) 0.12730(4) 0.0230(2) Uani 1 1 d . . . . .
C49 C 0.54535(17) 0.12056(17) 0.15539(4) 0.0231(2) Uani 1 1 d . . . . .
C50 C 0.38509(18) 0.0862(2) 0.15347(4) 0.0275(3) Uani 1 1 d . . . . .
H50 H 0.320245 0.115696 0.131361 0.033 Uiso 1 1 calc R U . . .
C51 C 0.32141(19) 0.0094(2) 0.18383(5) 0.0314(3) Uani 1 1 d . . . . .
H51 H 0.213057 -0.014128 0.182272 0.038 Uiso 1 1 calc R U . . .
C52 C 0.4147(2) -0.0343(2) 0.21684(4) 0.0308(3) Uani 1 1 d . . . . .
H52 H 0.367561 -0.083355 0.237719 0.037 Uiso 1 1 calc R U . . .
C53 C 0.5745(2) -0.00645(19) 0.21922(4) 0.0292(3) Uani 1 1 d . . . . .
H53 H 0.639029 -0.037910 0.241294 0.035 Uiso 1 1 calc R U . . .
C54 C 0.63885(17) 0.06906(17) 0.18839(4) 0.0244(2) Uani 1 1 d . . . . .
C55 C 0.42835(19) 0.2983(2) 0.07607(4) 0.0281(3) Uani 1 1 d . . . . .
C56 C 0.4008(2) 0.2542(2) 0.03412(5) 0.0357(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.7316(14) . ?
S1 C12 1.7371(13) . ?
S2 C15 1.7307(16) . ?
S2 C26 1.7421(15) . ?
S3 C29 1.7381(14) . ?
S3 C40 1.7388(14) . ?
S4 C54 1.7403(15) . ?
S4 C43 1.7415(16) . ?
F1 C14 1.324(2) . ?
F2 C14 1.330(2) . ?
F3 C14 1.320(2) . ?
F4 C28 1.330(2) . ?
F5 C28 1.329(2) . ?
F6 C28 1.307(2) . ?
F7 C42 1.3228(19) . ?
F8 C42 1.330(2) . ?
F9 C42 1.329(2) . ?
F10 C56 1.322(2) . ?
F11 C56 1.338(2) . ?
F12 C56 1.306(2) . ?
O1 C13 1.2069(17) . ?
O2 C27 1.2096(19) . ?
O3 C41 1.2057(17) . ?
O4 C55 1.2026(19) . ?
C1 C2 1.3950(19) . ?
C1 C6 1.4139(17) . ?
C2 C3 1.377(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.396(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.3948(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.4115(18) . ?
C5 C13 1.4822(18) . ?
C6 C7 1.4573(17) . ?
C7 C8 1.4084(18) . ?
C7 C12 1.4103(18) . ?
C8 C9 1.381(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.401(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.378(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.3911(19) . ?
C11 H11 0.9500 . ?
C13 C14 1.556(2) . ?
C15 C16 1.396(2) . ?
C15 C20 1.4142(19) . ?
C16 C17 1.380(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.394(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.400(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.414(2) . ?
C19 C27 1.478(2) . ?
C20 C21 1.4641(19) . ?
C21 C22 1.4054(19) . ?
C21 C26 1.4072(19) . ?
C22 C23 1.383(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.402(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.380(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.399(2) . ?
C25 H25 0.9500 . ?
C27 C28 1.553(2) . ?
C29 C30 1.397(2) . ?
C29 C34 1.4099(17) . ?
C30 C31 1.378(2) . ?
C30 H30 0.9500 . ?
C31 C32 1.392(2) . ?
C31 H31 0.9500 . ?
C32 C33 1.3984(19) . ?
C32 H32 0.9500 . ?
C33 C34 1.4199(19) . ?
C33 C41 1.4762(19) . ?
C34 C35 1.4642(19) . ?
C35 C36 1.4011(19) . ?
C35 C40 1.4090(18) . ?
C36 C37 1.387(2) . ?
C36 H36 0.9500 . ?
C37 C38 1.396(2) . ?
C37 H37 0.9500 . ?
C38 C39 1.382(2) . ?
C38 H38 0.9500 . ?
C39 C40 1.398(2) . ?
C39 H39 0.9500 . ?
C41 C42 1.550(2) . ?
C43 C44 1.396(2) . ?
C43 C48 1.4130(19) . ?
C44 C45 1.385(3) . ?
C44 H44 0.9500 . ?
C45 C46 1.395(2) . ?
C45 H45 0.9500 . ?
C46 C47 1.393(2) . ?
C46 H46 0.9500 . ?
C47 C48 1.420(2) . ?
C47 C55 1.482(2) . ?
C48 C49 1.4587(19) . ?
C49 C50 1.4028(19) . ?
C49 C54 1.4141(19) . ?
C50 C51 1.386(2) . ?
C50 H50 0.9500 . ?
C51 C52 1.404(2) . ?
C51 H51 0.9500 . ?
C52 C53 1.380(2) . ?
C52 H52 0.9500 . ?
C53 C54 1.395(2) . ?
C53 H53 0.9500 . ?
C55 C56 1.552(2) . ?

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 C12 90.80(6) . . ?
C15 S2 C26 91.48(7) . . ?
C29 S3 C40 91.46(6) . . ?
C54 S4 C43 91.13(7) . . ?
C2 C1 C6 122.96(13) . . ?
C2 C1 S1 123.35(10) . . ?
C6 C1 S1 113.67(10) . . ?
C3 C2 C1 118.59(13) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 120.35(13) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 121.09(13) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 120.08(12) . . ?
C4 C5 C13 116.56(12) . . ?
C6 C5 C13 123.28(11) . . ?
C5 C6 C1 116.90(11) . . ?
C5 C6 C7 132.08(11) . . ?
C1 C6 C7 110.88(11) . . ?
C8 C7 C12 117.61(12) . . ?
C8 C7 C6 131.19(12) . . ?
C12 C7 C6 111.13(11) . . ?
C9 C8 C7 120.01(13) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 120.98(13) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C11 C10 C9 120.39(13) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 118.62(13) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
C11 C12 C7 122.39(12) . . ?
C11 C12 S1 124.07(10) . . ?
C7 C12 S1 113.50(10) . . ?
O1 C13 C5 125.84(13) . . ?
O1 C13 C14 116.40(13) . . ?
C5 C13 C14 117.75(12) . . ?
F3 C14 F1 108.37(15) . . ?
F3 C14 F2 106.65(16) . . ?
F1 C14 F2 106.87(15) . . ?
F3 C14 C13 110.67(16) . . ?
F1 C14 C13 110.17(13) . . ?
F2 C14 C13 113.88(13) . . ?
C16 C15 C20 123.01(14) . . ?
C16 C15 S2 123.86(12) . . ?
C20 C15 S2 113.13(11) . . ?
C17 C16 C15 118.92(15) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C16 C17 C18 119.73(15) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C19 121.72(15) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 H18 119.1 . . ?
C18 C19 C20 119.71(14) . . ?
C18 C19 C27 117.26(14) . . ?
C20 C19 C27 122.80(12) . . ?
C19 C20 C15 116.84(13) . . ?
C19 C20 C21 132.06(12) . . ?
C15 C20 C21 111.06(12) . . ?
C22 C21 C26 117.50(13) . . ?
C22 C21 C20 130.95(13) . . ?
C26 C21 C20 111.42(12) . . ?
C23 C22 C21 120.48(14) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 120.60(14) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C25 C24 C23 120.51(14) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C24 C25 C26 118.43(14) . . ?
C24 C25 H25 120.8 . . ?
C26 C25 H25 120.8 . . ?
C25 C26 C21 122.39(13) . . ?
C25 C26 S2 124.72(11) . . ?
C21 C26 S2 112.85(11) . . ?
O2 C27 C19 125.78(14) . . ?
O2 C27 C28 116.33(14) . . ?
C19 C27 C28 117.88(13) . . ?
F6 C28 F5 107.98(17) . . ?
F6 C28 F4 108.40(17) . . ?
F5 C28 F4 105.09(14) . . ?
F6 C28 C27 110.65(14) . . ?
F5 C28 C27 111.27(15) . . ?
F4 C28 C27 113.18(14) . . ?
C30 C29 C34 123.20(13) . . ?
C30 C29 S3 123.66(11) . . ?
C34 C29 S3 113.13(10) . . ?
C31 C30 C29 119.09(13) . . ?
C31 C30 H30 120.5 . . ?
C29 C30 H30 120.5 . . ?
C30 C31 C32 119.79(13) . . ?
C30 C31 H31 120.1 . . ?
C32 C31 H31 120.1 . . ?
C31 C32 C33 121.35(14) . . ?
C31 C32 H32 119.3 . . ?
C33 C32 H32 119.3 . . ?
C32 C33 C34 120.29(12) . . ?
C32 C33 C41 116.54(12) . . ?
C34 C33 C41 123.12(12) . . ?
C29 C34 C33 116.23(12) . . ?
C29 C34 C35 110.99(11) . . ?
C33 C34 C35 132.68(11) . . ?
C36 C35 C40 116.89(12) . . ?
C36 C35 C34 131.42(12) . . ?
C40 C35 C34 111.67(11) . . ?
C37 C36 C35 120.51(13) . . ?
C37 C36 H36 119.7 . . ?
C35 C36 H36 119.7 . . ?
C36 C37 C38 121.36(14) . . ?
C36 C37 H37 119.3 . . ?
C38 C37 H37 119.3 . . ?
C39 C38 C37 119.72(14) . . ?
C39 C38 H38 120.1 . . ?
C37 C38 H38 120.1 . . ?
C38 C39 C40 118.59(13) . . ?
C38 C39 H39 120.7 . . ?
C40 C39 H39 120.7 . . ?
C39 C40 C35 122.91(12) . . ?
C39 C40 S3 124.33(10) . . ?
C35 C40 S3 112.74(10) . . ?
O3 C41 C33 126.52(13) . . ?
O3 C41 C42 116.24(13) . . ?
C33 C41 C42 117.23(12) . . ?
F7 C42 F9 108.29(15) . . ?
F7 C42 F8 107.12(15) . . ?
F9 C42 F8 106.85(15) . . ?
F7 C42 C41 109.86(13) . . ?
F9 C42 C41 110.79(15) . . ?
F8 C42 C41 113.71(13) . . ?
C44 C43 C48 122.65(15) . . ?
C44 C43 S4 124.02(12) . . ?
C48 C43 S4 113.32(11) . . ?
C45 C44 C43 118.64(15) . . ?
C45 C44 H44 120.7 . . ?
C43 C44 H44 120.7 . . ?
C44 C45 C46 120.45(15) . . ?
C44 C45 H45 119.8 . . ?
C46 C45 H45 119.8 . . ?
C47 C46 C45 121.03(16) . . ?
C47 C46 H46 119.5 . . ?
C45 C46 H46 119.5 . . ?
C46 C47 C48 120.01(14) . . ?
C46 C47 C55 117.07(14) . . ?
C48 C47 C55 122.68(12) . . ?
C43 C48 C47 117.13(13) . . ?
C43 C48 C49 110.91(12) . . ?
C47 C48 C49 131.92(12) . . ?
C50 C49 C54 117.76(13) . . ?
C50 C49 C48 130.45(13) . . ?
C54 C49 C48 111.68(12) . . ?
C51 C50 C49 119.98(14) . . ?
C51 C50 H50 120.0 . . ?
C49 C50 H50 120.0 . . ?
C50 C51 C52 120.92(14) . . ?
C50 C51 H51 119.5 . . ?
C52 C51 H51 119.5 . . ?
C53 C52 C51 120.52(14) . . ?
C53 C52 H52 119.7 . . ?
C51 C52 H52 119.7 . . ?
C52 C53 C54 118.31(14) . . ?
C52 C53 H53 120.8 . . ?
C54 C53 H53 120.8 . . ?
C53 C54 C49 122.42(13) . . ?
C53 C54 S4 124.67(11) . . ?
C49 C54 S4 112.88(11) . . ?
O4 C55 C47 125.62(14) . . ?
O4 C55 C56 116.15(15) . . ?
C47 C55 C56 118.22(13) . . ?
F12 C56 F10 108.79(18) . . ?
F12 C56 F11 107.71(19) . . ?
F10 C56 F11 105.12(15) . . ?
F12 C56 C55 110.94(15) . . ?
F10 C56 C55 112.85(14) . . ?
F11 C56 C55 111.15(15) . . ?

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
C12 S1 C1 C2 177.70(13) . . . . ?
C12 S1 C1 C6 -0.97(11) . . . . ?
C6 C1 C2 C3 0.7(2) . . . . ?
S1 C1 C2 C3 -177.83(12) . . . . ?
C1 C2 C3 C4 0.9(2) . . . . ?
C2 C3 C4 C5 -2.1(2) . . . . ?
C3 C4 C5 C6 1.5(2) . . . . ?
C3 C4 C5 C13 -175.22(14) . . . . ?
C4 C5 C6 C1 0.1(2) . . . . ?
C13 C5 C6 C1 176.62(13) . . . . ?
C4 C5 C6 C7 175.22(14) . . . . ?
C13 C5 C6 C7 -8.3(2) . . . . ?
C2 C1 C6 C5 -1.2(2) . . . . ?
S1 C1 C6 C5 177.44(10) . . . . ?
C2 C1 C6 C7 -177.36(13) . . . . ?
S1 C1 C6 C7 1.31(15) . . . . ?
C5 C6 C7 C8 0.4(3) . . . . ?
C1 C6 C7 C8 175.75(14) . . . . ?
C5 C6 C7 C12 -176.37(14) . . . . ?
C1 C6 C7 C12 -1.02(16) . . . . ?
C12 C7 C8 C9 -0.5(2) . . . . ?
C6 C7 C8 C9 -177.10(15) . . . . ?
C7 C8 C9 C10 -0.4(2) . . . . ?
C8 C9 C10 C11 0.9(2) . . . . ?
C9 C10 C11 C12 -0.4(2) . . . . ?
C10 C11 C12 C7 -0.5(2) . . . . ?
C10 C11 C12 S1 177.18(11) . . . . ?
C8 C7 C12 C11 1.0(2) . . . . ?
C6 C7 C12 C11 178.26(13) . . . . ?
C8 C7 C12 S1 -176.93(11) . . . . ?
C6 C7 C12 S1 0.32(14) . . . . ?
C1 S1 C12 C11 -177.54(13) . . . . ?
C1 S1 C12 C7 0.35(11) . . . . ?
C4 C5 C13 O1 133.87(16) . . . . ?
C6 C5 C13 O1 -42.8(2) . . . . ?
C4 C5 C13 C14 -45.02(19) . . . . ?
C6 C5 C13 C14 138.34(14) . . . . ?
O1 C13 C14 F3 -85.18(19) . . . . ?
C5 C13 C14 F3 93.81(18) . . . . ?
O1 C13 C14 F1 34.6(2) . . . . ?
C5 C13 C14 F1 -146.36(14) . . . . ?
O1 C13 C14 F2 154.69(15) . . . . ?
C5 C13 C14 F2 -26.3(2) . . . . ?
C26 S2 C15 C16 -179.70(14) . . . . ?
C26 S2 C15 C20 0.90(11) . . . . ?
C20 C15 C16 C17 -1.8(2) . . . . ?
S2 C15 C16 C17 178.83(13) . . . . ?
C15 C16 C17 C18 1.1(3) . . . . ?
C16 C17 C18 C19 1.3(3) . . . . ?
C17 C18 C19 C20 -3.0(2) . . . . ?
C17 C18 C19 C27 171.65(15) . . . . ?
C18 C19 C20 C15 2.2(2) . . . . ?
C27 C19 C20 C15 -172.13(13) . . . . ?
C18 C19 C20 C21 -175.64(14) . . . . ?
C27 C19 C20 C21 10.0(2) . . . . ?
C16 C15 C20 C19 0.2(2) . . . . ?
S2 C15 C20 C19 179.56(10) . . . . ?
C16 C15 C20 C21 178.44(14) . . . . ?
S2 C15 C20 C21 -2.15(15) . . . . ?
C19 C20 C21 C22 4.8(3) . . . . ?
C15 C20 C21 C22 -173.11(15) . . . . ?
C19 C20 C21 C26 -179.45(14) . . . . ?
C15 C20 C21 C26 2.61(16) . . . . ?
C26 C21 C22 C23 2.1(2) . . . . ?
C20 C21 C22 C23 177.63(15) . . . . ?
C21 C22 C23 C24 0.6(2) . . . . ?
C22 C23 C24 C25 -2.0(3) . . . . ?
C23 C24 C25 C26 0.7(2) . . . . ?
C24 C25 C26 C21 2.1(2) . . . . ?
C24 C25 C26 S2 -175.53(12) . . . . ?
C22 C21 C26 C25 -3.5(2) . . . . ?
C20 C21 C26 C25 -179.86(13) . . . . ?
C22 C21 C26 S2 174.38(11) . . . . ?
C20 C21 C26 S2 -1.97(15) . . . . ?
C15 S2 C26 C25 178.48(14) . . . . ?
C15 S2 C26 C21 0.65(11) . . . . ?
C18 C19 C27 O2 -133.88(18) . . . . ?
C20 C19 C27 O2 40.6(2) . . . . ?
C18 C19 C27 C28 44.8(2) . . . . ?
C20 C19 C27 C28 -140.70(15) . . . . ?
O2 C27 C28 F6 -31.7(2) . . . . ?
C19 C27 C28 F6 149.51(18) . . . . ?
O2 C27 C28 F5 88.4(2) . . . . ?
C19 C27 C28 F5 -90.45(19) . . . . ?
O2 C27 C28 F4 -153.54(16) . . . . ?
C19 C27 C28 F4 27.6(2) . . . . ?
C40 S3 C29 C30 179.22(13) . . . . ?
C40 S3 C29 C34 0.11(11) . . . . ?
C34 C29 C30 C31 1.1(2) . . . . ?
S3 C29 C30 C31 -177.92(12) . . . . ?
C29 C30 C31 C32 1.3(2) . . . . ?
C30 C31 C32 C33 -2.6(2) . . . . ?
C31 C32 C33 C34 1.4(2) . . . . ?
C31 C32 C33 C41 -176.14(15) . . . . ?
C30 C29 C34 C33 -2.1(2) . . . . ?
S3 C29 C34 C33 176.97(10) . . . . ?
C30 C29 C34 C35 -178.86(13) . . . . ?
S3 C29 C34 C35 0.26(15) . . . . ?
C32 C33 C34 C29 0.9(2) . . . . ?
C41 C33 C34 C29 178.27(13) . . . . ?
C32 C33 C34 C35 176.69(14) . . . . ?
C41 C33 C34 C35 -5.9(2) . . . . ?
C29 C34 C35 C36 177.72(15) . . . . ?
C33 C34 C35 C36 1.7(3) . . . . ?
C29 C34 C35 C40 -0.60(16) . . . . ?
C33 C34 C35 C40 -176.59(14) . . . . ?
C40 C35 C36 C37 -0.5(2) . . . . ?
C34 C35 C36 C37 -178.73(16) . . . . ?
C35 C36 C37 C38 -0.7(3) . . . . ?
C36 C37 C38 C39 1.5(3) . . . . ?
C37 C38 C39 C40 -1.1(2) . . . . ?
C38 C39 C40 C35 -0.1(2) . . . . ?
C38 C39 C40 S3 178.55(12) . . . . ?
C36 C35 C40 C39 0.9(2) . . . . ?
C34 C35 C40 C39 179.50(13) . . . . ?
C36 C35 C40 S3 -177.90(12) . . . . ?
C34 C35 C40 S3 0.70(15) . . . . ?
C29 S3 C40 C39 -179.25(13) . . . . ?
C29 S3 C40 C35 -0.47(11) . . . . ?
C32 C33 C41 O3 134.84(17) . . . . ?
C34 C33 C41 O3 -42.7(2) . . . . ?
C32 C33 C41 C42 -43.8(2) . . . . ?
C34 C33 C41 C42 138.67(14) . . . . ?
O3 C41 C42 F7 33.1(2) . . . . ?
C33 C41 C42 F7 -148.08(14) . . . . ?
O3 C41 C42 F9 -86.50(19) . . . . ?
C33 C41 C42 F9 92.31(18) . . . . ?
O3 C41 C42 F8 153.15(16) . . . . ?
C33 C41 C42 F8 -28.0(2) . . . . ?
C54 S4 C43 C44 -179.15(14) . . . . ?
C54 S4 C43 C48 1.69(11) . . . . ?
C48 C43 C44 C45 -1.9(2) . . . . ?
S4 C43 C44 C45 178.97(13) . . . . ?
C43 C44 C45 C46 1.3(3) . . . . ?
C44 C45 C46 C47 1.3(3) . . . . ?
C45 C46 C47 C48 -3.3(2) . . . . ?
C45 C46 C47 C55 171.15(15) . . . . ?
C44 C43 C48 C47 0.0(2) . . . . ?
S4 C43 C48 C47 179.20(10) . . . . ?
C44 C43 C48 C49 178.09(14) . . . . ?
S4 C43 C48 C49 -2.74(15) . . . . ?
C46 C47 C48 C43 2.6(2) . . . . ?
C55 C47 C48 C43 -171.56(13) . . . . ?
C46 C47 C48 C49 -174.99(15) . . . . ?
C55 C47 C48 C49 10.9(2) . . . . ?
C43 C48 C49 C50 -173.40(15) . . . . ?
C47 C48 C49 C50 4.3(3) . . . . ?
C43 C48 C49 C54 2.60(16) . . . . ?
C47 C48 C49 C54 -179.71(14) . . . . ?
C54 C49 C50 C51 2.1(2) . . . . ?
C48 C49 C50 C51 177.94(15) . . . . ?
C49 C50 C51 C52 0.4(2) . . . . ?
C50 C51 C52 C53 -2.2(3) . . . . ?
C51 C52 C53 C54 1.3(2) . . . . ?
C52 C53 C54 C49 1.3(2) . . . . ?
C52 C53 C54 S4 -176.71(12) . . . . ?
C50 C49 C54 C53 -3.0(2) . . . . ?
C48 C49 C54 C53 -179.60(13) . . . . ?
C50 C49 C54 S4 175.18(11) . . . . ?
C48 C49 C54 S4 -1.38(15) . . . . ?
C43 S4 C54 C53 178.03(13) . . . . ?
C43 S4 C54 C49 -0.14(11) . . . . ?
C46 C47 C55 O4 -131.02(18) . . . . ?
C48 C47 C55 O4 43.3(2) . . . . ?
C46 C47 C55 C56 47.7(2) . . . . ?
C48 C47 C55 C56 -137.98(15) . . . . ?
O4 C55 C56 F12 -33.9(3) . . . . ?
C47 C55 C56 F12 147.19(19) . . . . ?
O4 C55 C56 F10 -156.32(17) . . . . ?
C47 C55 C56 F10 24.8(2) . . . . ?
O4 C55 C56 F11 85.9(2) . . . . ?
C47 C55 C56 F11 -92.99(19) . . . . ?

_refine_diff_density_max         1.163
_refine_diff_density_min         -0.760
_refine_diff_density_rms         0.131

