# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_735
_database_code_depnum_ccdc_archive 'CCDC 1991009'
loop_
_audit_author_name
_audit_author_address
'Nallappan Sundaravelu'
;Indian Institute of Technology, Madras
India
;
_audit_update_record             
;
2020-03-17 deposited with the CCDC.	2020-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H13 F O S2'
_chemical_formula_sum            'C22 H13 F O S2'
_chemical_formula_weight         376.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
O O 0.0106 0.0060 '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                   11.3658(11)
_cell_length_b                   12.2954(9)
_cell_length_c                   12.4661(14)
_cell_angle_alpha                90
_cell_angle_beta                 102.113(5)
_cell_angle_gamma                90
_cell_volume                     1703.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1416
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      20.75

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.331
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10253
_diffrn_reflns_av_unetI/netI     0.0730
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.353
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_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             3000
_reflns_number_gt                1766
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0359P)²+0.2122P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3000
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1012
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.0995
_refine_ls_wR_factor_gt          0.0781
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_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
C1 C 0.1641(3) -0.0089(2) -0.0644(2) 0.0370(7) Uani 1 1 d . . . . .
C2 C 0.1577(3) -0.1066(2) -0.1236(3) 0.0493(9) Uani 1 1 d . . . . .
H2 H 0.2199 -0.1570 -0.1072 0.059 Uiso 1 1 calc R U . . .
C3 C 0.0604(4) -0.1275(3) -0.2049(3) 0.0587(10) Uani 1 1 d . . . . .
H3 H 0.0569 -0.1920 -0.2443 0.070 Uiso 1 1 calc R U . . .
C4 C -0.0343(3) -0.0537(3) -0.2299(3) 0.0595(10) Uani 1 1 d . . . . .
H4 H -0.1011 -0.0691 -0.2850 0.071 Uiso 1 1 calc R U . . .
C5 C -0.0282(3) 0.0424(2) -0.1725(3) 0.0481(9) Uani 1 1 d . . . . .
H5 H -0.0910 0.0921 -0.1896 0.058 Uiso 1 1 calc R U . . .
C6 C 0.0710(3) 0.0666(2) -0.0888(2) 0.0368(7) Uani 1 1 d . . . . .
C7 C 0.0735(3) 0.1715(2) -0.0308(2) 0.0371(7) Uani 1 1 d . . . . .
C8 C 0.1791(3) 0.20140(19) 0.0538(2) 0.0331(7) Uani 1 1 d . . . . .
C9 C 0.1715(3) 0.31449(19) 0.1008(2) 0.0372(7) Uani 1 1 d . . . . .
H9 H 0.0854 0.3283 0.0951 0.045 Uiso 1 1 calc R U . . .
C10 C 0.3746(3) 0.2545(2) 0.2451(3) 0.0410(8) Uani 1 1 d . . . . .
C11 C 0.4731(3) 0.2823(2) 0.3266(3) 0.0550(9) Uani 1 1 d . . . . .
H11 H 0.4663 0.3382 0.3752 0.066 Uiso 1 1 calc R U . . .
C12 C 0.5803(3) 0.2283(3) 0.3363(3) 0.0631(10) Uani 1 1 d . . . . .
H12 H 0.6454 0.2469 0.3918 0.076 Uiso 1 1 calc R U . . .
C13 C 0.5913(3) 0.1464(3) 0.2639(3) 0.0599(10) Uani 1 1 d . . . . .
H13 H 0.6638 0.1093 0.2709 0.072 Uiso 1 1 calc R U . . .
C14 C 0.4954(3) 0.1193(2) 0.1810(3) 0.0485(9) Uani 1 1 d . . . . .
H14 H 0.5048 0.0653 0.1312 0.058 Uiso 1 1 calc R U . . .
C15 C 0.3838(3) 0.1716(2) 0.1703(2) 0.0378(7) Uani 1 1 d . . . . .
C16 C 0.2780(3) 0.1384(2) 0.0861(2) 0.0349(7) Uani 1 1 d . . . . .
C17 C 0.2151(2) 0.40467(19) 0.0368(2) 0.0334(7) Uani 1 1 d . . . . .
C18 C 0.3091(3) 0.3911(2) -0.0174(2) 0.0402(8) Uani 1 1 d . . . . .
H18 H 0.3464 0.3236 -0.0156 0.048 Uiso 1 1 calc R U . . .
C19 C 0.3481(3) 0.4756(2) -0.0736(3) 0.0475(8) Uani 1 1 d . . . . .
H19 H 0.4117 0.4665 -0.1092 0.057 Uiso 1 1 calc R U . . .
C20 C 0.2906(3) 0.5728(2) -0.0754(3) 0.0517(9) Uani 1 1 d . . . . .
C21 C 0.1983(3) 0.5909(2) -0.0232(3) 0.0497(9) Uani 1 1 d . . . . .
H21 H 0.1616 0.6587 -0.0260 0.060 Uiso 1 1 calc R U . . .
C22 C 0.1610(3) 0.5065(2) 0.0335(2) 0.0399(8) Uani 1 1 d . . . . .
H22 H 0.0987 0.5174 0.0702 0.048 Uiso 1 1 calc R U . . .
F1 F 0.32806(19) 0.65661(14) -0.13153(19) 0.0889(7) Uani 1 1 d . . . . .
O1 O -0.01166(19) 0.23510(16) -0.05563(18) 0.0548(6) Uani 1 1 d . . . . .
S1 S 0.29254(7) 0.00867(5) 0.03624(7) 0.0475(3) Uani 1 1 d . . . . .
S2 S 0.23787(8) 0.31940(6) 0.24575(7) 0.0512(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
C1 C6 1.392(4) . ?
C1 C2 1.404(4) . ?
C1 S1 1.728(3) . ?
C2 C3 1.358(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.398(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.476(4) . ?
C7 O1 1.233(3) . ?
C7 C8 1.468(4) . ?
C8 C16 1.355(4) . ?
C8 C9 1.518(3) . ?
C9 C17 1.509(3) . ?
C9 S2 1.807(3) . ?
C9 H9 0.9800 . ?
C10 C11 1.387(4) . ?
C10 C15 1.401(4) . ?
C10 S2 1.748(3) . ?
C11 C12 1.371(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.376(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.404(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.477(4) . ?
C16 S1 1.732(3) . ?
C17 C18 1.388(4) . ?
C17 C22 1.391(3) . ?
C18 C19 1.378(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.360(4) . ?
C19 H19 0.9300 . ?
C20 F1 1.363(3) . ?
C20 C21 1.363(4) . ?
C21 C22 1.373(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.2(3) . . ?
C6 C1 S1 124.3(2) . . ?
C2 C1 S1 115.5(2) . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 121.1(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.6(3) . . ?
C1 C6 C7 122.7(3) . . ?
C5 C6 C7 118.8(3) . . ?
O1 C7 C8 120.1(2) . . ?
O1 C7 C6 119.8(3) . . ?
C8 C7 C6 120.0(3) . . ?
C16 C8 C7 124.9(2) . . ?
C16 C8 C9 121.3(3) . . ?
C7 C8 C9 113.7(2) . . ?
C17 C9 C8 114.6(2) . . ?
C17 C9 S2 112.91(19) . . ?
C8 C9 S2 111.75(19) . . ?
C17 C9 H9 105.5 . . ?
C8 C9 H9 105.5 . . ?
S2 C9 H9 105.5 . . ?
C11 C10 C15 120.4(3) . . ?
C11 C10 S2 117.8(3) . . ?
C15 C10 S2 121.7(3) . . ?
C12 C11 C10 120.7(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 119.9(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C14 120.2(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C15 121.2(3) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C10 C15 C14 117.5(3) . . ?
C10 C15 C16 120.7(3) . . ?
C14 C15 C16 121.7(3) . . ?
C8 C16 C15 123.6(2) . . ?
C8 C16 S1 123.7(2) . . ?
C15 C16 S1 112.6(2) . . ?
C18 C17 C22 118.4(2) . . ?
C18 C17 C9 122.7(2) . . ?
C22 C17 C9 118.9(2) . . ?
C19 C18 C17 121.3(2) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C20 C19 C18 117.8(3) . . ?
C20 C19 H19 121.1 . . ?
C18 C19 H19 121.1 . . ?
C19 C20 F1 118.1(3) . . ?
C19 C20 C21 123.4(3) . . ?
F1 C20 C21 118.4(3) . . ?
C20 C21 C22 118.3(3) . . ?
C20 C21 H21 120.8 . . ?
C22 C21 H21 120.8 . . ?
C21 C22 C17 120.8(3) . . ?
C21 C22 H22 119.6 . . ?
C17 C22 H22 119.6 . . ?
C1 S1 C16 104.26(14) . . ?
C10 S2 C9 99.52(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.1(4) . . . . ?
S1 C1 C2 C3 -179.6(2) . . . . ?
C1 C2 C3 C4 -0.7(5) . . . . ?
C2 C3 C4 C5 0.9(5) . . . . ?
C3 C4 C5 C6 -0.6(5) . . . . ?
C2 C1 C6 C5 0.3(4) . . . . ?
S1 C1 C6 C5 179.9(2) . . . . ?
C2 C1 C6 C7 -178.9(2) . . . . ?
S1 C1 C6 C7 0.7(4) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
C4 C5 C6 C7 179.2(3) . . . . ?
C1 C6 C7 O1 -179.8(3) . . . . ?
C5 C6 C7 O1 1.0(4) . . . . ?
C1 C6 C7 C8 2.2(4) . . . . ?
C5 C6 C7 C8 -177.0(2) . . . . ?
O1 C7 C8 C16 -179.0(3) . . . . ?
C6 C7 C8 C16 -1.0(4) . . . . ?
O1 C7 C8 C9 -1.6(4) . . . . ?
C6 C7 C8 C9 176.4(2) . . . . ?
C16 C8 C9 C17 91.2(3) . . . . ?
C7 C8 C9 C17 -86.3(3) . . . . ?
C16 C8 C9 S2 -38.9(3) . . . . ?
C7 C8 C9 S2 143.6(2) . . . . ?
C15 C10 C11 C12 -0.9(4) . . . . ?
S2 C10 C11 C12 174.6(2) . . . . ?
C10 C11 C12 C13 0.8(5) . . . . ?
C11 C12 C13 C14 0.6(5) . . . . ?
C12 C13 C14 C15 -1.9(5) . . . . ?
C11 C10 C15 C14 -0.4(4) . . . . ?
S2 C10 C15 C14 -175.7(2) . . . . ?
C11 C10 C15 C16 177.4(3) . . . . ?
S2 C10 C15 C16 2.1(4) . . . . ?
C13 C14 C15 C10 1.8(4) . . . . ?
C13 C14 C15 C16 -176.0(3) . . . . ?
C7 C8 C16 C15 178.9(2) . . . . ?
C9 C8 C16 C15 1.7(4) . . . . ?
C7 C8 C16 S1 -2.9(4) . . . . ?
C9 C8 C16 S1 179.83(19) . . . . ?
C10 C15 C16 C8 19.7(4) . . . . ?
C14 C15 C16 C8 -162.7(3) . . . . ?
C10 C15 C16 S1 -158.6(2) . . . . ?
C14 C15 C16 S1 19.0(3) . . . . ?
C8 C9 C17 C18 -33.8(4) . . . . ?
S2 C9 C17 C18 95.7(3) . . . . ?
C8 C9 C17 C22 147.6(3) . . . . ?
S2 C9 C17 C22 -82.9(3) . . . . ?
C22 C17 C18 C19 -0.3(4) . . . . ?
C9 C17 C18 C19 -178.9(3) . . . . ?
C17 C18 C19 C20 -0.7(5) . . . . ?
C18 C19 C20 F1 -179.5(3) . . . . ?
C18 C19 C20 C21 1.1(5) . . . . ?
C19 C20 C21 C22 -0.4(5) . . . . ?
F1 C20 C21 C22 -179.8(3) . . . . ?
C20 C21 C22 C17 -0.6(4) . . . . ?
C18 C17 C22 C21 1.0(4) . . . . ?
C9 C17 C22 C21 179.6(3) . . . . ?
C6 C1 S1 C16 -3.7(3) . . . . ?
C2 C1 S1 C16 175.9(2) . . . . ?
C8 C16 S1 C1 4.8(3) . . . . ?
C15 C16 S1 C1 -176.88(19) . . . . ?
C11 C10 S2 C9 151.5(2) . . . . ?
C15 C10 S2 C9 -33.0(2) . . . . ?
C17 C9 S2 C10 -82.2(2) . . . . ?
C8 C9 S2 C10 48.8(2) . . . . ?

_refine_diff_density_max         0.212
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.052



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_764
_database_code_depnum_ccdc_archive 'CCDC 1991010'
loop_
_audit_author_name
_audit_author_address
'Nallappan Sundaravelu'
;Indian Institute of Technology, Madras
India
;
_audit_update_record             
;
2020-03-17 deposited with the CCDC.	2020-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H16 O S2'
_chemical_formula_weight         372.48

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                   11.1152(3)
_cell_length_b                   12.7185(4)
_cell_length_c                   12.9078(5)
_cell_angle_alpha                90
_cell_angle_beta                 103.7030(14)
_cell_angle_gamma                90
_cell_volume                     1772.82(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5027
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      26.54

_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.309
_shelx_estimated_absorpt_T_min   0.927
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13793
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.886
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_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             3124
_reflns_number_gt                2490
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0321P)²+0.9607P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3124
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0843
_refine_ls_wR_factor_gt          0.0757
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.988
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.06517(17) 0.93307(14) -0.08912(15) 0.0362(4) Uani 1 1 d . . . . .
C2 C -0.03210(19) 0.95699(17) -0.17696(17) 0.0472(5) Uani 1 1 d . . . . .
H2 H -0.0977 0.9101 -0.1972 0.057 Uiso 1 1 calc R U . . .
C3 C -0.0322(2) 1.04819(18) -0.23341(18) 0.0560(6) Uani 1 1 d . . . . .
H3 H -0.0978 1.0628 -0.2912 0.067 Uiso 1 1 calc R U . . .
C4 C 0.0645(2) 1.11852(18) -0.20500(18) 0.0567(6) Uani 1 1 d . . . . .
H4 H 0.0644 1.1801 -0.2439 0.068 Uiso 1 1 calc R U . . .
C5 C 0.1605(2) 1.09760(16) -0.11948(18) 0.0505(5) Uani 1 1 d . . . . .
H5 H 0.2253 1.1454 -0.1001 0.061 Uiso 1 1 calc R U . . .
C6 C 0.16195(18) 1.00488(14) -0.06099(16) 0.0378(4) Uani 1 1 d . . . . .
C7 C 0.27039(17) 0.86235(14) 0.09209(15) 0.0357(4) Uani 1 1 d . . . . .
C8 C 0.37739(17) 0.82868(15) 0.17751(15) 0.0382(4) Uani 1 1 d . . . . .
C9 C 0.49288(18) 0.87796(17) 0.19295(16) 0.0457(5) Uani 1 1 d . . . . .
H9 H 0.5038 0.9307 0.1461 0.055 Uiso 1 1 calc R U . . .
C10 C 0.5909(2) 0.85032(19) 0.27571(18) 0.0551(6) Uani 1 1 d . . . . .
H10 H 0.6660 0.8857 0.2857 0.066 Uiso 1 1 calc R U . . .
C11 C 0.5770(2) 0.7702(2) 0.34350(19) 0.0586(6) Uani 1 1 d . . . . .
H11 H 0.6432 0.7509 0.3989 0.070 Uiso 1 1 calc R U . . .
C12 C 0.4659(2) 0.71871(17) 0.32971(17) 0.0531(6) Uani 1 1 d . . . . .
H12 H 0.4578 0.6641 0.3754 0.064 Uiso 1 1 calc R U . . .
C13 C 0.36475(19) 0.74740(16) 0.24778(15) 0.0423(5) Uani 1 1 d . . . . .
C14 C 0.15829(17) 0.69254(14) 0.09727(15) 0.0377(4) Uani 1 1 d . . . . .
H14 H 0.0696 0.6778 0.0861 0.045 Uiso 1 1 calc R U . . .
C15 C 0.16792(16) 0.80226(14) 0.05485(15) 0.0350(4) Uani 1 1 d . . . . .
C16 C 0.06265(17) 0.83271(15) -0.03223(16) 0.0382(4) Uani 1 1 d . . . . .
C17 C 0.20991(16) 0.60769(14) 0.03797(14) 0.0328(4) Uani 1 1 d . . . . .
C18 C 0.16381(17) 0.50562(14) 0.03549(16) 0.0380(4) Uani 1 1 d . . . . .
H18 H 0.1022 0.4904 0.0709 0.046 Uiso 1 1 calc R U . . .
C19 C 0.20809(17) 0.42715(15) -0.01855(16) 0.0414(5) Uani 1 1 d . . . . .
H19 H 0.1749 0.3599 -0.0200 0.050 Uiso 1 1 calc R U . . .
C20 C 0.30143(17) 0.44642(14) -0.07096(16) 0.0396(5) Uani 1 1 d . . . . .
C21 C 0.34878(18) 0.54738(15) -0.06690(16) 0.0404(5) Uani 1 1 d . . . . .
H21 H 0.4125 0.5619 -0.1002 0.048 Uiso 1 1 calc R U . . .
C22 C 0.30310(17) 0.62698(14) -0.01428(15) 0.0381(4) Uani 1 1 d . . . . .
H22 H 0.3354 0.6945 -0.0139 0.046 Uiso 1 1 calc R U . . .
C23 C 0.3496(2) 0.36192(17) -0.1321(2) 0.0600(6) Uani 1 1 d . . . . .
H23A H 0.4051 0.3170 -0.0832 0.090 Uiso 1 1 calc R U . . .
H23B H 0.3929 0.3937 -0.1802 0.090 Uiso 1 1 calc R U . . .
H23C H 0.2815 0.3212 -0.1720 0.090 Uiso 1 1 calc R U . . .
O1 O -0.02648(13) 0.77279(12) -0.05985(13) 0.0577(4) Uani 1 1 d . . . . .
S1 S 0.28918(5) 0.98779(4) 0.04520(5) 0.04672(16) Uani 1 1 d . . . . .
S2 S 0.22236(5) 0.68570(4) 0.24056(4) 0.05098(17) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.392(3) . ?
C1 C2 1.402(3) . ?
C1 C16 1.476(3) . ?
C2 C3 1.370(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.398(3) . ?
C5 H5 0.9300 . ?
C6 S1 1.734(2) . ?
C7 C15 1.361(3) . ?
C7 C8 1.481(3) . ?
C7 S1 1.7364(19) . ?
C8 C9 1.400(3) . ?
C8 C13 1.404(3) . ?
C9 C10 1.379(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.375(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.372(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.397(3) . ?
C12 H12 0.9300 . ?
C13 S2 1.749(2) . ?
C14 C17 1.513(3) . ?
C14 C15 1.512(3) . ?
C14 S2 1.820(2) . ?
C14 H14 0.9800 . ?
C15 C16 1.469(3) . ?
C16 O1 1.234(2) . ?
C17 C22 1.385(2) . ?
C17 C18 1.393(2) . ?
C18 C19 1.374(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.388(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.384(3) . ?
C20 C23 1.505(3) . ?
C21 C22 1.381(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 117.96(18) . . ?
C6 C1 C16 122.82(18) . . ?
C2 C1 C16 119.21(18) . . ?
C3 C2 C1 121.1(2) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 120.4(2) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 119.9(2) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 120.20(19) . . ?
C1 C6 S1 123.99(15) . . ?
C5 C6 S1 115.81(16) . . ?
C15 C7 C8 123.91(17) . . ?
C15 C7 S1 123.53(15) . . ?
C8 C7 S1 112.55(13) . . ?
C9 C8 C13 117.80(19) . . ?
C9 C8 C7 121.63(18) . . ?
C13 C8 C7 120.55(17) . . ?
C10 C9 C8 121.7(2) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C9 C10 C11 119.6(2) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C12 120.3(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C13 120.8(2) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C8 119.7(2) . . ?
C12 C13 S2 118.61(17) . . ?
C8 C13 S2 121.58(16) . . ?
C17 C14 C15 114.04(15) . . ?
C17 C14 S2 112.10(13) . . ?
C15 C14 S2 111.59(13) . . ?
C17 C14 H14 106.1 . . ?
C15 C14 H14 106.1 . . ?
S2 C14 H14 106.1 . . ?
C7 C15 C16 124.76(17) . . ?
C7 C15 C14 121.02(17) . . ?
C16 C15 C14 114.10(16) . . ?
O1 C16 C15 119.85(18) . . ?
O1 C16 C1 119.93(18) . . ?
C15 C16 C1 120.19(16) . . ?
C22 C17 C18 117.85(17) . . ?
C22 C17 C14 122.48(16) . . ?
C18 C17 C14 119.67(16) . . ?
C19 C18 C17 120.96(17) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C20 121.21(17) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C21 C20 C19 117.83(17) . . ?
C21 C20 C23 120.21(18) . . ?
C19 C20 C23 121.95(18) . . ?
C22 C21 C20 121.19(17) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C21 C22 C17 120.93(17) . . ?
C21 C22 H22 119.5 . . ?
C17 C22 H22 119.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C6 S1 C7 104.34(9) . . ?
C13 S2 C14 99.44(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.1(3) . . . . ?
C16 C1 C2 C3 -178.61(18) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
C16 C1 C6 C5 178.51(17) . . . . ?
C2 C1 C6 S1 179.96(14) . . . . ?
C16 C1 C6 S1 -1.5(3) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C4 C5 C6 S1 179.81(17) . . . . ?
C15 C7 C8 C9 161.87(18) . . . . ?
S1 C7 C8 C9 -18.7(2) . . . . ?
C15 C7 C8 C13 -19.8(3) . . . . ?
S1 C7 C8 C13 159.58(15) . . . . ?
C13 C8 C9 C10 -1.7(3) . . . . ?
C7 C8 C9 C10 176.68(18) . . . . ?
C8 C9 C10 C11 2.0(3) . . . . ?
C9 C10 C11 C12 -0.7(3) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C11 C12 C13 C8 1.1(3) . . . . ?
C11 C12 C13 S2 -175.14(16) . . . . ?
C9 C8 C13 C12 0.1(3) . . . . ?
C7 C8 C13 C12 -178.24(17) . . . . ?
C9 C8 C13 S2 176.25(14) . . . . ?
C7 C8 C13 S2 -2.1(3) . . . . ?
C8 C7 C15 C16 -177.85(16) . . . . ?
S1 C7 C15 C16 2.8(3) . . . . ?
C8 C7 C15 C14 -2.0(3) . . . . ?
S1 C7 C15 C14 178.63(13) . . . . ?
C17 C14 C15 C7 -88.8(2) . . . . ?
S2 C14 C15 C7 39.5(2) . . . . ?
C17 C14 C15 C16 87.48(19) . . . . ?
S2 C14 C15 C16 -144.24(13) . . . . ?
C7 C15 C16 O1 -179.61(18) . . . . ?
C14 C15 C16 O1 4.3(2) . . . . ?
C7 C15 C16 C1 2.5(3) . . . . ?
C14 C15 C16 C1 -173.62(15) . . . . ?
C6 C1 C16 O1 178.99(18) . . . . ?
C2 C1 C16 O1 -2.5(3) . . . . ?
C6 C1 C16 C15 -3.1(3) . . . . ?
C2 C1 C16 C15 175.37(17) . . . . ?
C15 C14 C17 C22 27.4(3) . . . . ?
S2 C14 C17 C22 -100.59(18) . . . . ?
C15 C14 C17 C18 -153.01(17) . . . . ?
S2 C14 C17 C18 78.96(19) . . . . ?
C22 C17 C18 C19 -1.0(3) . . . . ?
C14 C17 C18 C19 179.39(17) . . . . ?
C17 C18 C19 C20 1.0(3) . . . . ?
C18 C19 C20 C21 0.1(3) . . . . ?
C18 C19 C20 C23 -178.9(2) . . . . ?
C19 C20 C21 C22 -1.3(3) . . . . ?
C23 C20 C21 C22 177.8(2) . . . . ?
C20 C21 C22 C17 1.3(3) . . . . ?
C18 C17 C22 C21 -0.1(3) . . . . ?
C14 C17 C22 C21 179.44(18) . . . . ?
C1 C6 S1 C7 5.49(18) . . . . ?
C5 C6 S1 C7 -174.57(15) . . . . ?
C15 C7 S1 C6 -6.09(18) . . . . ?
C8 C7 S1 C6 174.47(13) . . . . ?
C12 C13 S2 C14 -150.56(16) . . . . ?
C8 C13 S2 C14 33.26(17) . . . . ?
C17 C14 S2 C13 79.82(14) . . . . ?
C15 C14 S2 C13 -49.49(14) . . . . ?

_refine_diff_density_max         0.185
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.045



