# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1442210'
_audit_update_record             
;
2015-12-14 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(Z)-3-benzylidenebenzo[c]thiophene-1(3H)-thione
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H10 S2'
_chemical_formula_weight         254.35

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

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

_cell_length_a                   5.7002(4)
_cell_length_b                   13.2911(16)
_cell_length_c                   16.3160(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1236.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    124
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.025
_exptl_absorpt_coefficient_mu    0.402
_shelx_estimated_absorpt_T_min   0.906
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.808
_exptl_absorpt_correction_T_max  0.879
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15019
_diffrn_reflns_av_unetI/netI     0.0693
_diffrn_reflns_av_R_equivalents  0.1138
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.786
_diffrn_reflns_theta_max         27.510
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2829
_reflns_number_gt                1948
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.706
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.993

_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       'COLLECT (Nonius, 2002)'
_computing_cell_refinement       
'DIRAX (Duisenberg,1992; Duisenberg et al., 2003)'
_computing_data_reduction        'EVAL (Nonius, 2002; Duisenberg et al., 2000)'
_computing_structure_solution    'SIR2014 (Burla et al., 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  
'WinGX (Farrugia, 2012) and publCIF (Westrip, 2010)'
_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)+(0.0625P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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 604 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2829
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1228
_refine_ls_wR_factor_gt          0.1037
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_restrained_S_all      0.969
_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 0.0994(2) 0.11137(9) 0.22447(7) 0.0539(3) Uani 1 1 d . . . . .
S2 S -0.3030(3) 0.02626(11) 0.13206(9) 0.0710(4) Uani 1 1 d . . . . .
C1 C -0.1476(7) 0.2258(3) 0.1261(2) 0.0452(10) Uani 1 1 d . . . . .
C2 C 0.1854(7) 0.2389(3) 0.2149(2) 0.0463(9) Uani 1 1 d . . . . .
C3 C 0.3660(8) 0.2842(4) 0.2545(2) 0.0489(10) Uani 1 1 d . . . . .
C4 C 0.5274(7) 0.2474(4) 0.3167(2) 0.0475(10) Uani 1 1 d . . . . .
C5 C 0.0325(8) 0.3907(4) 0.1334(3) 0.0545(11) Uani 1 1 d . . . . .
H5 H 0.1478 0.4338 0.1532 0.065 Uiso 1 1 calc R U . . .
C6 C 0.0273(8) 0.2889(3) 0.1572(3) 0.0446(10) Uani 1 1 d . . . . .
C7 C -0.1339(8) 0.1223(3) 0.1563(2) 0.0493(10) Uani 1 1 d . . . . .
C8 C 0.7145(8) 0.3118(4) 0.3392(3) 0.0553(11) Uani 1 1 d . . . . .
H8 H 0.7313 0.3738 0.3134 0.066 Uiso 1 1 calc R U . . .
C9 C 0.6677(9) 0.1293(4) 0.4186(3) 0.0594(12) Uani 1 1 d . . . . .
H9 H 0.6519 0.0680 0.4455 0.071 Uiso 1 1 calc R U . . .
C10 C -0.1387(9) 0.4257(4) 0.0794(3) 0.0588(12) Uani 1 1 d . . . . .
H10 H -0.1365 0.4928 0.0632 0.071 Uiso 1 1 calc R U . . .
C11 C -0.3115(9) 0.3627(4) 0.0494(3) 0.0587(12) Uani 1 1 d . . . . .
H11 H -0.4239 0.3879 0.0135 0.070 Uiso 1 1 calc R U . . .
C12 C -0.3186(8) 0.2626(4) 0.0724(3) 0.0533(11) Uani 1 1 d . . . . .
H12 H -0.4354 0.2203 0.0524 0.064 Uiso 1 1 calc R U . . .
C13 C 0.8492(9) 0.1933(4) 0.4392(3) 0.0626(13) Uani 1 1 d . . . . .
H13 H 0.9554 0.1754 0.4799 0.075 Uiso 1 1 calc R U . . .
C14 C 0.5098(8) 0.1558(4) 0.3584(3) 0.0559(11) Uani 1 1 d . . . . .
H14 H 0.3888 0.1118 0.3451 0.067 Uiso 1 1 calc R U . . .
C15 C 0.8718(9) 0.2836(4) 0.3990(3) 0.0607(13) Uani 1 1 d . . . . .
H15 H 0.9953 0.3262 0.4123 0.073 Uiso 1 1 calc R U . . .
H100 H 0.378(9) 0.363(4) 0.243(3) 0.073 Uiso 1 1 d . 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 C7 1.740(5) . ?
S1 C2 1.772(4) . ?
S2 C7 1.647(5) . ?
C1 C6 1.398(6) . ?
C1 C12 1.400(6) . ?
C1 C7 1.463(6) . ?
C2 C3 1.357(6) . ?
C2 C6 1.462(6) . ?
C3 C4 1.455(6) . ?
C4 C14 1.397(6) . ?
C4 C8 1.416(6) . ?
C5 C10 1.394(7) . ?
C5 C6 1.408(6) . ?
C8 C15 1.376(7) . ?
C9 C14 1.379(6) . ?
C9 C13 1.381(7) . ?
C10 C11 1.382(7) . ?
C11 C12 1.384(7) . ?
C13 C15 1.373(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 S1 C2 94.3(2) . . ?
C6 C1 C12 120.9(4) . . ?
C6 C1 C7 113.8(4) . . ?
C12 C1 C7 125.2(4) . . ?
C3 C2 C6 125.0(4) . . ?
C3 C2 S1 126.3(3) . . ?
C6 C2 S1 108.7(3) . . ?
C2 C3 C4 131.6(4) . . ?
C14 C4 C8 117.0(4) . . ?
C14 C4 C3 125.9(4) . . ?
C8 C4 C3 117.0(4) . . ?
C10 C5 C6 118.7(4) . . ?
C1 C6 C5 119.4(4) . . ?
C1 C6 C2 113.6(4) . . ?
C5 C6 C2 127.0(4) . . ?
C1 C7 S2 128.0(3) . . ?
C1 C7 S1 109.5(3) . . ?
S2 C7 S1 122.5(3) . . ?
C15 C8 C4 120.6(5) . . ?
C14 C9 C13 120.3(5) . . ?
C11 C10 C5 121.4(4) . . ?
C12 C11 C10 120.5(5) . . ?
C11 C12 C1 119.1(4) . . ?
C15 C13 C9 119.5(5) . . ?
C9 C14 C4 121.5(4) . . ?
C13 C15 C8 121.0(5) . . ?

_refine_diff_density_max         0.163
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1442211'
_audit_update_record             
;
2015-12-14 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(Z)-3-(4-fluorobenzylidene)benzo[c]thiophene-1(3H)-thione
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 O S2'
_chemical_formula_weight         284.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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/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                   3.9659(5)
_cell_length_b                   16.3382(4)
_cell_length_c                   20.518(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.920(16)
_cell_angle_gamma                90
_cell_volume                     1328.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    126
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.025
_exptl_absorpt_coefficient_mu    0.388
_shelx_estimated_absorpt_T_min   0.876
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.808
_exptl_absorpt_correction_T_max  0.879
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26857
_diffrn_reflns_av_unetI/netI     0.0783
_diffrn_reflns_av_R_equivalents  0.1354
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.345
_diffrn_reflns_theta_max         27.639
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3085
_reflns_number_gt                1719
_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       'COLLECT (Nonius, 2002)'
_computing_cell_refinement       
'DIRAX (Duisenberg,1992; Duisenberg et al., 2003)'
_computing_data_reduction        'EVAL (Nonius, 2002; Duisenberg et al., 2000)'
_computing_structure_solution    'SIR2014 (Burla et al., 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  
'WinGX (Farrugia, 2012) and publCIF (Westrip, 2010)'
_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)+(0.0448P)²+0.5801P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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_number_reflns         3085
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1313
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1278
_refine_ls_wR_factor_gt          0.1030
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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 0.0949(2) 0.03568(5) 0.17373(4) 0.0419(2) Uani 1 1 d . . . . .
S2 S 0.0283(2) 0.17908(5) 0.25078(5) 0.0569(3) Uani 1 1 d . . . . .
O1 O 0.3940(6) -0.25688(14) -0.03908(11) 0.0550(6) Uani 1 1 d . . . . .
C1 C -0.1919(7) 0.02816(19) 0.29484(14) 0.0406(7) Uani 1 1 d . . . . .
C2 C 0.0863(7) -0.11496(17) 0.11732(14) 0.0355(7) Uani 1 1 d . . . . .
C3 C -0.0144(7) -0.06791(18) 0.17493(14) 0.0357(7) Uani 1 1 d . . . . .
C4 C -0.0396(7) 0.07925(18) 0.24530(15) 0.0396(7) Uani 1 1 d . . . . .
C5 C 0.2954(7) -0.20637(19) 0.00987(14) 0.0406(7) Uani 1 1 d . . . . .
C6 C 0.0840(8) -0.20005(19) 0.11795(16) 0.0491(8) Uani 1 1 d . . . . .
H6 H 0.0111 -0.2273 0.1547 0.059 Uiso 1 1 calc R U . . .
C7 C -0.1695(8) -0.0992(2) 0.22673(16) 0.0422(7) Uani 1 1 d . . . . .
H7 H -0.236(7) -0.152(2) 0.2240(15) 0.048(9) Uiso 1 1 d . . . . .
C8 C -0.2550(7) -0.05616(19) 0.28481(14) 0.0385(7) Uani 1 1 d . . . . .
C9 C 0.1877(9) -0.2451(2) 0.06518(16) 0.0546(9) Uani 1 1 d . . . . .
H9 H 0.1848 -0.3020 0.0670 0.066 Uiso 1 1 calc R U . . .
C10 C -0.4051(8) -0.1006(2) 0.33503(16) 0.0505(8) Uani 1 1 d . . . . .
H10 H -0.4498 -0.1560 0.3289 0.061 Uiso 1 1 calc R U . . .
C11 C 0.2958(8) -0.1227(2) 0.00741(16) 0.0493(8) Uani 1 1 d . . . . .
H11 H 0.3648 -0.0959 -0.0299 0.059 Uiso 1 1 calc R U . . .
C12 C -0.2779(9) 0.0638(2) 0.35413(16) 0.0523(9) Uani 1 1 d . . . . .
H12 H -0.2373 0.1193 0.3611 0.063 Uiso 1 1 calc R U . . .
C13 C 0.1933(8) -0.0779(2) 0.06056(16) 0.0493(8) Uani 1 1 d . . . . .
H13 H 0.1960 -0.0211 0.0582 0.059 Uiso 1 1 calc R U . . .
C14 C -0.4867(9) -0.0646(2) 0.39246(17) 0.0591(10) Uani 1 1 d . . . . .
H14 H -0.5854 -0.0954 0.4248 0.071 Uiso 1 1 calc R U . . .
C15 C 0.5327(8) -0.2205(2) -0.09518(15) 0.0524(9) Uani 1 1 d . . . . .
H15A H 0.6036 -0.2626 -0.1243 0.079 Uiso 1 1 calc R U . . .
H15B H 0.7231 -0.1873 -0.0822 0.079 Uiso 1 1 calc R U . . .
H15C H 0.3649 -0.1869 -0.1169 0.079 Uiso 1 1 calc R U . . .
C16 C -0.4216(10) 0.0181(2) 0.40234(17) 0.0627(10) Uani 1 1 d . . . . .
H16 H -0.4751 0.0427 0.4416 0.075 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 C4 1.732(3) . ?
S1 C3 1.747(3) . ?
S2 C4 1.656(3) . ?
O1 C5 1.367(3) . ?
O1 C15 1.422(4) . ?
C1 C12 1.401(4) . ?
C1 C8 1.414(4) . ?
C1 C4 1.462(4) . ?
C2 C6 1.390(4) . ?
C2 C13 1.391(4) . ?
C2 C3 1.476(4) . ?
C3 C7 1.347(4) . ?
C5 C11 1.368(4) . ?
C5 C9 1.380(4) . ?
C6 C9 1.383(4) . ?
C7 C8 1.434(4) . ?
C8 C10 1.409(4) . ?
C10 C14 1.365(4) . ?
C11 C13 1.386(4) . ?
C12 C16 1.378(5) . ?
C14 C16 1.390(5) . ?

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
C4 S1 C3 107.61(15) . . ?
C5 O1 C15 118.0(2) . . ?
C12 C1 C8 119.0(3) . . ?
C12 C1 C4 119.0(3) . . ?
C8 C1 C4 122.0(3) . . ?
C6 C2 C13 116.4(3) . . ?
C6 C2 C3 120.7(3) . . ?
C13 C2 C3 122.8(3) . . ?
C7 C3 C2 125.3(3) . . ?
C7 C3 S1 119.9(2) . . ?
C2 C3 S1 114.8(2) . . ?
C1 C4 S2 125.8(2) . . ?
C1 C4 S1 120.1(2) . . ?
S2 C4 S1 114.10(18) . . ?
O1 C5 C11 125.1(3) . . ?
O1 C5 C9 115.5(3) . . ?
C11 C5 C9 119.3(3) . . ?
C9 C6 C2 121.5(3) . . ?
C3 C7 C8 126.7(3) . . ?
C10 C8 C1 118.2(3) . . ?
C10 C8 C7 118.2(3) . . ?
C1 C8 C7 123.6(3) . . ?
C5 C9 C6 120.5(3) . . ?
C14 C10 C8 121.8(3) . . ?
C5 C11 C13 119.9(3) . . ?
C16 C12 C1 121.1(3) . . ?
C11 C13 C2 122.3(3) . . ?
C10 C14 C16 119.8(3) . . ?
C12 C16 C14 120.1(3) . . ?

_refine_diff_density_max         0.203
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.056

