# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_[12+](BF4)2
_database_code_depnum_ccdc_archive 'CCDC 1581480'
_audit_update_record             
;
2017-10-23 deposited with the CCDC.
2018-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 O2 S8, 2(B F4)'
_chemical_formula_sum            'C16 H14 B2 F8 O2 S8'
_chemical_formula_weight         668.37

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'
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'

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

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

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

_cell_length_a                   10.7366(4)
_cell_length_b                   11.0614(5)
_cell_length_c                   21.0424(11)
_cell_angle_alpha                90
_cell_angle_beta                 101.460(4)
_cell_angle_gamma                90
_cell_volume                     2449.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3841
_cell_measurement_theta_min      3.5420
_cell_measurement_theta_max      29.6950

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.813
_exptl_crystal_F_000             1344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.807
_shelx_estimated_absorpt_T_min   0.862
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0107
_diffrn_reflns_number            10396
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.979
_diffrn_reflns_theta_max         29.808
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.865
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.865
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6081
_reflns_number_gt                4696
_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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    SHELXL-2017/1
_computing_publication_material  SHELXL-2017/1
_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)+(0.0363P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6081
_refine_ls_number_parameters     329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0892
_refine_ls_wR_factor_gt          0.0800
_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 0.55010(5) 0.74826(6) 0.64135(3) 0.01753(13) Uani 1 1 d . . . . .
S2 S 0.41096(5) 0.65189(6) 0.74073(3) 0.01848(14) Uani 1 1 d . . . . .
S3 S 0.18793(5) 0.58641(6) 0.64745(3) 0.01778(14) Uani 1 1 d . . . . .
S4 S 0.27671(5) 0.69687(6) 0.53591(3) 0.01828(14) Uani 1 1 d . . . . .
S5 S 0.26876(5) 0.56393(6) 0.85644(3) 0.02097(15) Uani 1 1 d . . . . .
S6 S 0.03196(5) 0.58634(6) 0.76613(3) 0.01851(14) Uani 1 1 d . . . . .
S7 S 0.14233(6) 0.53081(6) 0.97070(3) 0.02064(14) Uani 1 1 d . . . . .
S8 S -0.12433(5) 0.56852(6) 0.86928(3) 0.01926(14) Uani 1 1 d . . . . .
O1 O 0.55683(15) 0.60662(16) 0.37138(8) 0.0219(4) Uani 1 1 d . . . . .
O2 O 0.76783(14) 0.62717(16) 0.45440(8) 0.0218(4) Uani 1 1 d . . . . .
C1 C 0.4150(2) 0.6829(2) 0.66126(11) 0.0155(5) Uani 1 1 d . . . . .
C2 C 0.3057(2) 0.6576(2) 0.61736(11) 0.0157(5) Uani 1 1 d . . . . .
C3 C 0.4291(2) 0.6729(2) 0.51768(11) 0.0149(5) Uani 1 1 d . . . . .
C4 C 0.4308(2) 0.6400(2) 0.45394(11) 0.0152(5) Uani 1 1 d . . . . .
H4 H 0.353302 0.624687 0.424345 0.018 Uiso 1 1 calc R U . . .
C5 C 0.5453(2) 0.6298(2) 0.43378(11) 0.0160(5) Uani 1 1 d . . . . .
C6 C 0.6610(2) 0.6427(2) 0.47900(11) 0.0161(5) Uani 1 1 d . . . . .
C7 C 0.6588(2) 0.6712(2) 0.54312(11) 0.0159(5) Uani 1 1 d . . . . .
H7 H 0.735984 0.677623 0.574117 0.019 Uiso 1 1 calc R U . . .
C8 C 0.5425(2) 0.6903(2) 0.56172(11) 0.0146(5) Uani 1 1 d . . . . .
C9 C 0.2592(2) 0.6004(2) 0.72638(11) 0.0163(5) Uani 1 1 d . . . . .
C10 C 0.1928(2) 0.5820(2) 0.77854(11) 0.0180(5) Uani 1 1 d . . . . .
C11 C 0.1359(2) 0.5558(2) 0.88934(11) 0.0150(5) Uani 1 1 d . . . . .
C12 C 0.0201(2) 0.5676(2) 0.84519(11) 0.0154(5) Uani 1 1 d . . . . .
C13 C 0.3109(2) 0.5176(3) 1.00054(12) 0.0287(6) Uani 1 1 d . . . . .
H13A H 0.344546 0.451592 0.977832 0.043 Uiso 1 1 calc R U . . .
H13B H 0.327284 0.500429 1.047149 0.043 Uiso 1 1 calc R U . . .
H13C H 0.352555 0.593510 0.992876 0.043 Uiso 1 1 calc R U . . .
C14 C -0.2330(2) 0.5674(3) 0.79194(12) 0.0241(6) Uani 1 1 d . . . . .
H14A H -0.221539 0.641184 0.767974 0.036 Uiso 1 1 calc R U . . .
H14B H -0.320559 0.563788 0.798886 0.036 Uiso 1 1 calc R U . . .
H14C H -0.216075 0.496631 0.766959 0.036 Uiso 1 1 calc R U . . .
C15 C 0.4401(2) 0.5987(2) 0.32473(11) 0.0215(5) Uani 1 1 d . . . . .
H15A H 0.392376 0.527533 0.334030 0.032 Uiso 1 1 calc R U . . .
H15B H 0.458678 0.591504 0.281137 0.032 Uiso 1 1 calc R U . . .
H15C H 0.389435 0.671638 0.327133 0.032 Uiso 1 1 calc R U . . .
C16 C 0.8877(2) 0.6283(3) 0.49913(13) 0.0258(6) Uani 1 1 d . . . . .
H16A H 0.899051 0.706321 0.521570 0.039 Uiso 1 1 calc R U . . .
H16B H 0.956493 0.615952 0.475410 0.039 Uiso 1 1 calc R U . . .
H16C H 0.889242 0.563297 0.530937 0.039 Uiso 1 1 calc R U . . .
F1 F -0.11285(13) 0.32957(14) 0.71933(7) 0.0278(4) Uani 1 1 d . . . . .
F2 F -0.15154(15) 0.45838(14) 0.63392(8) 0.0382(4) Uani 1 1 d . . . . .
F3 F -0.13374(16) 0.25677(15) 0.61695(8) 0.0396(4) Uani 1 1 d . . . . .
F4 F 0.04125(14) 0.36669(15) 0.66190(8) 0.0363(4) Uani 1 1 d . . . . .
B1 B -0.0892(3) 0.3521(3) 0.65715(14) 0.0215(6) Uani 1 1 d . . . . .
F5 F 0.53287(14) 0.47113(14) 0.84922(7) 0.0292(4) Uani 1 1 d . . . . .
F6 F 0.58643(14) 0.27248(16) 0.84345(8) 0.0371(4) Uani 1 1 d . . . . .
F7 F 0.44462(13) 0.33059(14) 0.90526(7) 0.0261(3) Uani 1 1 d . . . . .
F8 F 0.38903(13) 0.33847(14) 0.79473(7) 0.0277(3) Uani 1 1 d . . . . .
B2 B 0.4885(3) 0.3515(3) 0.84782(14) 0.0199(6) 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 1.744(2) . ?
S1 C8 1.781(2) . ?
S2 C9 1.696(2) . ?
S2 C1 1.716(2) . ?
S3 C9 1.692(2) . ?
S3 C2 1.714(2) . ?
S4 C2 1.735(2) . ?
S4 C3 1.773(2) . ?
S5 C10 1.692(2) . ?
S5 C11 1.707(2) . ?
S6 C10 1.695(2) . ?
S6 C12 1.706(2) . ?
S7 C11 1.722(2) . ?
S7 C13 1.800(2) . ?
S8 C12 1.725(2) . ?
S8 C14 1.804(2) . ?
O1 C5 1.367(3) . ?
O1 C15 1.433(3) . ?
O2 C6 1.360(3) . ?
O2 C16 1.435(3) . ?
C1 C2 1.370(3) . ?
C3 C8 1.390(3) . ?
C3 C4 1.393(3) . ?
C4 C5 1.382(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.414(3) . ?
C6 C7 1.390(3) . ?
C7 C8 1.397(3) . ?
C7 H7 0.9500 . ?
C9 C10 1.437(3) . ?
C11 C12 1.402(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
F1 B1 1.404(3) . ?
F2 B1 1.393(3) . ?
F3 B1 1.376(3) . ?
F4 B1 1.394(3) . ?
F5 B2 1.404(3) . ?
F6 B2 1.385(3) . ?
F7 B2 1.401(3) . ?
F8 B2 1.391(3) . ?

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 C8 101.07(11) . . ?
C9 S2 C1 95.93(11) . . ?
C9 S3 C2 95.61(11) . . ?
C2 S4 C3 100.61(11) . . ?
C10 S5 C11 96.79(11) . . ?
C10 S6 C12 96.73(11) . . ?
C11 S7 C13 101.46(11) . . ?
C12 S8 C14 101.14(11) . . ?
C5 O1 C15 115.80(18) . . ?
C6 O2 C16 117.59(18) . . ?
C2 C1 S2 115.58(17) . . ?
C2 C1 S1 124.35(18) . . ?
S2 C1 S1 120.02(13) . . ?
C1 C2 S3 116.14(17) . . ?
C1 C2 S4 125.20(17) . . ?
S3 C2 S4 118.61(13) . . ?
C8 C3 C4 120.1(2) . . ?
C8 C3 S4 123.99(18) . . ?
C4 C3 S4 115.89(17) . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
O1 C5 C4 124.5(2) . . ?
O1 C5 C6 115.45(19) . . ?
C4 C5 C6 120.1(2) . . ?
O2 C6 C7 125.2(2) . . ?
O2 C6 C5 115.2(2) . . ?
C7 C6 C5 119.6(2) . . ?
C6 C7 C8 119.6(2) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C3 C8 C7 120.4(2) . . ?
C3 C8 S1 123.21(17) . . ?
C7 C8 S1 116.22(17) . . ?
C10 C9 S3 122.72(17) . . ?
C10 C9 S2 121.11(18) . . ?
S3 C9 S2 115.89(13) . . ?
C9 C10 S5 122.66(18) . . ?
C9 C10 S6 121.55(18) . . ?
S5 C10 S6 115.67(13) . . ?
C12 C11 S5 115.36(17) . . ?
C12 C11 S7 121.92(17) . . ?
S5 C11 S7 122.69(14) . . ?
C11 C12 S6 115.44(16) . . ?
C11 C12 S8 122.43(17) . . ?
S6 C12 S8 122.10(13) . . ?
S7 C13 H13A 109.5 . . ?
S7 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
S7 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
S8 C14 H14A 109.5 . . ?
S8 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
S8 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
F3 B1 F2 110.3(2) . . ?
F3 B1 F4 110.8(2) . . ?
F2 B1 F4 109.5(2) . . ?
F3 B1 F1 109.4(2) . . ?
F2 B1 F1 108.3(2) . . ?
F4 B1 F1 108.6(2) . . ?
F6 B2 F8 110.7(2) . . ?
F6 B2 F7 110.0(2) . . ?
F8 B2 F7 109.9(2) . . ?
F6 B2 F5 109.7(2) . . ?
F8 B2 F5 108.5(2) . . ?
F7 B2 F5 108.0(2) . . ?

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
C9 S2 C1 C2 -0.3(2) . . . . ?
C9 S2 C1 S1 177.12(15) . . . . ?
C8 S1 C1 C2 -31.7(2) . . . . ?
C8 S1 C1 S2 151.07(15) . . . . ?
S2 C1 C2 S3 -5.8(3) . . . . ?
S1 C1 C2 S3 176.87(13) . . . . ?
S2 C1 C2 S4 171.66(14) . . . . ?
S1 C1 C2 S4 -5.6(3) . . . . ?
C9 S3 C2 C1 8.7(2) . . . . ?
C9 S3 C2 S4 -168.91(15) . . . . ?
C3 S4 C2 C1 38.0(2) . . . . ?
C3 S4 C2 S3 -144.59(14) . . . . ?
C2 S4 C3 C8 -32.3(2) . . . . ?
C2 S4 C3 C4 150.69(19) . . . . ?
C8 C3 C4 C5 -2.8(4) . . . . ?
S4 C3 C4 C5 174.35(18) . . . . ?
C15 O1 C5 C4 3.0(3) . . . . ?
C15 O1 C5 C6 -177.3(2) . . . . ?
C3 C4 C5 O1 -175.1(2) . . . . ?
C3 C4 C5 C6 5.2(4) . . . . ?
C16 O2 C6 C7 6.5(3) . . . . ?
C16 O2 C6 C5 -174.4(2) . . . . ?
O1 C5 C6 O2 -1.7(3) . . . . ?
C4 C5 C6 O2 178.0(2) . . . . ?
O1 C5 C6 C7 177.4(2) . . . . ?
C4 C5 C6 C7 -2.9(4) . . . . ?
O2 C6 C7 C8 177.0(2) . . . . ?
C5 C6 C7 C8 -2.0(3) . . . . ?
C4 C3 C8 C7 -2.1(4) . . . . ?
S4 C3 C8 C7 -178.98(18) . . . . ?
C4 C3 C8 S1 172.87(18) . . . . ?
S4 C3 C8 S1 -4.0(3) . . . . ?
C6 C7 C8 C3 4.5(3) . . . . ?
C6 C7 C8 S1 -170.88(18) . . . . ?
C1 S1 C8 C3 36.2(2) . . . . ?
C1 S1 C8 C7 -148.64(18) . . . . ?
C2 S3 C9 C10 165.0(2) . . . . ?
C2 S3 C9 S2 -8.91(16) . . . . ?
C1 S2 C9 C10 -167.6(2) . . . . ?
C1 S2 C9 S3 6.42(16) . . . . ?
S3 C9 C10 S5 165.51(14) . . . . ?
S2 C9 C10 S5 -20.9(3) . . . . ?
S3 C9 C10 S6 -18.6(3) . . . . ?
S2 C9 C10 S6 154.96(15) . . . . ?
C11 S5 C10 C9 176.9(2) . . . . ?
C11 S5 C10 S6 0.80(17) . . . . ?
C12 S6 C10 C9 -176.6(2) . . . . ?
C12 S6 C10 S5 -0.47(17) . . . . ?
C10 S5 C11 C12 -0.9(2) . . . . ?
C10 S5 C11 S7 177.43(16) . . . . ?
C13 S7 C11 C12 177.6(2) . . . . ?
C13 S7 C11 S5 -0.58(19) . . . . ?
S5 C11 C12 S6 0.7(3) . . . . ?
S7 C11 C12 S6 -177.62(13) . . . . ?
S5 C11 C12 S8 -177.12(13) . . . . ?
S7 C11 C12 S8 4.5(3) . . . . ?
C10 S6 C12 C11 -0.2(2) . . . . ?
C10 S6 C12 S8 177.70(16) . . . . ?
C14 S8 C12 C11 -173.4(2) . . . . ?
C14 S8 C12 S6 8.90(19) . . . . ?

_refine_diff_density_max         0.435
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.085

####################################################################### 
# 
# 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_bip305_a(1)
_database_code_depnum_ccdc_archive 'CCDC 1586984'
_audit_update_record             
;
2017-11-21 deposited with the CCDC.
2018-03-21 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            'C16 H14 O2 S8'
_chemical_formula_weight         494.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   31.739(3)
_cell_length_b                   4.5314(4)
_cell_length_c                   14.5044(12)
_cell_angle_alpha                90
_cell_angle_beta                 101.228(5)
_cell_angle_gamma                90
_cell_volume                     2046.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3003
_cell_measurement_theta_min      4.260
_cell_measurement_theta_max      68.241

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    8.175
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5003
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'omega + phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9755
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.260
_diffrn_reflns_theta_max         68.241
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measured_fraction_theta_full 0.919
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_Laue_measured_fraction_full 0.919
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_point_group_measured_fraction_full 0.919
_reflns_number_total             3555
_reflns_number_gt                3003
_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       'APEX2 (Bruker, 2012)'
_computing_cell_refinement       'APEX2 (Bruker, 2012)'
_computing_data_reduction        'SAINT+ (Bruker, 2009)'
_computing_structure_solution    'SHELXT-2014/7, intrinsic phasing'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond 3D, Version 4.0 (Brandenburg, 2014)'
_computing_publication_material  shelxle
_refine_special_details          'ACTA 50 instead of ACTA for cif-generation'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0486P)²+3.3038P] 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         3555
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.1040
_refine_ls_wR_factor_gt          0.0987
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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 0.91093(3) 0.3969(2) 0.07833(6) 0.0221(2) Uani 1 1 d . . . . .
C1 C 0.87190(12) 0.1636(8) 0.0066(3) 0.0213(8) Uani 1 1 d . . . . .
H1A H 0.8477 0.2838 -0.0252 0.032 Uiso 1 1 calc R U . . .
H1B H 0.8615 0.0162 0.0463 0.032 Uiso 1 1 calc R U . . .
H1C H 0.8852 0.0635 -0.0404 0.032 Uiso 1 1 calc R U . . .
O1 O 0.54578(8) 0.4386(6) 0.47328(18) 0.0237(6) Uani 1 1 d . . . . .
S2 S 0.95451(3) 0.7961(2) 0.26181(6) 0.0211(2) Uani 1 1 d . . . . .
C2 C 0.97046(12) 0.6113(9) 0.3737(3) 0.0257(8) Uani 1 1 d . . . . .
H2A H 0.9647 0.3994 0.3657 0.039 Uiso 1 1 calc R U . . .
H2B H 0.9541 0.6916 0.4187 0.039 Uiso 1 1 calc R U . . .
H2C H 1.0012 0.6428 0.3975 0.039 Uiso 1 1 calc R U . . .
O2 O 0.58636(8) 0.7639(6) 0.60647(18) 0.0238(6) Uani 1 1 d . . . . .
S3 S 0.82549(3) 0.50281(18) 0.13843(6) 0.0167(2) Uani 1 1 d . . . . .
C3 C 0.88207(11) 0.5400(7) 0.1595(2) 0.0152(7) Uani 1 1 d . . . . .
S4 S 0.86515(3) 0.86111(18) 0.30107(6) 0.0169(2) Uani 1 1 d . . . . .
C4 C 0.89998(11) 0.7006(8) 0.2340(2) 0.0167(7) Uani 1 1 d . . . . .
S6 S 0.78536(3) 0.76944(18) 0.39963(6) 0.01506(19) Uani 1 1 d . . . . .
C6 C 0.78673(11) 0.6107(7) 0.2894(2) 0.0146(7) Uani 1 1 d . . . . .
S5 S 0.73941(3) 0.41665(19) 0.24073(6) 0.0166(2) Uani 1 1 d . . . . .
C5 C 0.82086(11) 0.6498(7) 0.2481(2) 0.0151(7) Uani 1 1 d . . . . .
S8 S 0.73534(3) 0.50604(19) 0.53686(6) 0.0171(2) Uani 1 1 d . . . . .
C8 C 0.74626(10) 0.5231(7) 0.4233(2) 0.0152(7) Uani 1 1 d . . . . .
S7 S 0.68366(3) 0.11820(18) 0.36063(6) 0.0171(2) Uani 1 1 d . . . . .
C7 C 0.72515(10) 0.3634(7) 0.3514(2) 0.0137(7) Uani 1 1 d . . . . .
C9 C 0.65641(11) 0.3260(7) 0.4358(2) 0.0146(7) Uani 1 1 d . . . . .
C10 C 0.67840(11) 0.4918(7) 0.5086(2) 0.0156(7) Uani 1 1 d . . . . .
C11 C 0.61164(11) 0.3038(7) 0.4206(2) 0.0166(7) Uani 1 1 d . . . . .
H11 H 0.5967 0.1897 0.3696 0.020 Uiso 1 1 calc R U . . .
C12 C 0.65567(11) 0.6473(8) 0.5674(2) 0.0179(7) Uani 1 1 d . . . . .
H12 H 0.6707 0.7668 0.6169 0.021 Uiso 1 1 calc R U . . .
C13 C 0.58891(11) 0.4481(8) 0.4799(2) 0.0179(7) Uani 1 1 d . . . . .
C14 C 0.61132(11) 0.6257(7) 0.5529(2) 0.0172(7) Uani 1 1 d . . . . .
C15 C 0.52228(11) 0.2386(9) 0.4059(3) 0.0280(9) Uani 1 1 d . . . . .
H15A H 0.5243 0.3027 0.3424 0.042 Uiso 1 1 calc R U . . .
H15B H 0.4921 0.2364 0.4121 0.042 Uiso 1 1 calc R U . . .
H15C H 0.5344 0.0399 0.4172 0.042 Uiso 1 1 calc R U . . .
C16 C 0.60794(12) 0.9459(9) 0.6814(3) 0.0249(8) Uani 1 1 d . . . . .
H16A H 0.6232 1.1047 0.6557 0.037 Uiso 1 1 calc R U . . .
H16B H 0.6286 0.8265 0.7250 0.037 Uiso 1 1 calc R U . . .
H16C H 0.5869 1.0314 0.7149 0.037 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 C3 1.751(3) . ?
S1 C1 1.798(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
O1 C13 1.354(4) . ?
O1 C15 1.431(4) . ?
S2 C4 1.753(3) . ?
S2 C2 1.809(4) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
O2 C14 1.365(4) . ?
O2 C16 1.429(4) . ?
S3 C5 1.757(3) . ?
S3 C3 1.770(3) . ?
C3 C4 1.334(5) . ?
S4 C5 1.750(4) . ?
S4 C4 1.765(3) . ?
S6 C8 1.752(3) . ?
S6 C6 1.762(3) . ?
C6 C5 1.347(4) . ?
C6 S5 1.765(4) . ?
S5 C7 1.768(3) . ?
S8 C8 1.749(3) . ?
S8 C10 1.775(3) . ?
C8 C7 1.337(5) . ?
S7 C7 1.748(3) . ?
S7 C9 1.786(3) . ?
C9 C10 1.372(5) . ?
C9 C11 1.398(5) . ?
C10 C12 1.408(4) . ?
C11 C13 1.389(4) . ?
C11 H11 0.9500 . ?
C12 C14 1.386(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.407(5) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
C3 S1 C1 102.42(16) . . ?
S1 C1 H1A 109.5 . . ?
S1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
S1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C13 O1 C15 117.0(3) . . ?
C4 S2 C2 100.58(16) . . ?
S2 C2 H2A 109.5 . . ?
S2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
S2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C14 O2 C16 116.9(3) . . ?
C5 S3 C3 93.93(16) . . ?
C4 C3 S1 123.4(3) . . ?
C4 C3 S3 116.7(2) . . ?
S1 C3 S3 119.6(2) . . ?
C5 S4 C4 93.93(16) . . ?
C3 C4 S2 124.5(2) . . ?
C3 C4 S4 117.2(3) . . ?
S2 C4 S4 117.9(2) . . ?
C8 S6 C6 93.52(16) . . ?
C5 C6 S6 120.9(3) . . ?
C5 C6 S5 125.7(3) . . ?
S6 C6 S5 113.39(17) . . ?
C6 S5 C7 93.04(15) . . ?
C6 C5 S4 121.6(3) . . ?
C6 C5 S3 124.6(3) . . ?
S4 C5 S3 113.76(17) . . ?
C8 S8 C10 99.44(15) . . ?
C7 C8 S8 123.3(2) . . ?
C7 C8 S6 117.3(2) . . ?
S8 C8 S6 119.4(2) . . ?
C7 S7 C9 99.96(15) . . ?
C8 C7 S7 123.7(2) . . ?
C8 C7 S5 117.2(2) . . ?
S7 C7 S5 119.1(2) . . ?
C10 C9 C11 120.6(3) . . ?
C10 C9 S7 121.6(2) . . ?
C11 C9 S7 117.7(3) . . ?
C9 C10 C12 119.8(3) . . ?
C9 C10 S8 122.7(2) . . ?
C12 C10 S8 117.5(3) . . ?
C13 C11 C9 120.2(3) . . ?
C13 C11 H11 119.9 . . ?
C9 C11 H11 119.9 . . ?
C14 C12 C10 119.9(3) . . ?
C14 C12 H12 120.1 . . ?
C10 C12 H12 120.1 . . ?
O1 C13 C11 125.5(3) . . ?
O1 C13 C14 115.3(3) . . ?
C11 C13 C14 119.2(3) . . ?
O2 C14 C12 124.5(3) . . ?
O2 C14 C13 115.2(3) . . ?
C12 C14 C13 120.3(3) . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_refine_diff_density_max         0.494
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.087

