# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_aks10
_database_code_depnum_ccdc_archive 'CCDC 1479463'
_audit_update_record             
;
2016-05-12 deposited with the CCDC.
2016-07-18 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         'C23 H20 S'
_chemical_formula_sum            'C23 H20 S'
_chemical_formula_weight         328.45

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      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                   9.756(4)
_cell_length_b                   10.716(5)
_cell_length_c                   10.881(4)
_cell_angle_alpha                65.921(18)
_cell_angle_beta                 68.070(16)
_cell_angle_gamma                63.361(19)
_cell_volume                     902.6(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5722
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      26.05

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_F_000             348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.179
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.986
_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            20194
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.402
_diffrn_reflns_theta_max         26.559
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3729
_reflns_number_gt                2835
_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)+(0.0549P)²+0.2322P] 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         3729
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1232
_refine_ls_wR_factor_gt          0.1129
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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 0.37895(5) 0.81611(5) 0.67928(5) 0.04641(17) Uani 1 1 d . . . . .
C9 C 0.5757(2) 0.7444(2) 0.30533(18) 0.0408(4) Uani 1 1 d . . . . .
C8 C 0.5259(2) 0.74429(19) 0.45170(17) 0.0389(4) Uani 1 1 d . . . . .
C15 C 0.6127(2) 0.63529(19) 0.55389(17) 0.0394(4) Uani 1 1 d . . . . .
C6 C 0.2760(2) 0.9725(2) 0.43714(18) 0.0411(4) Uani 1 1 d . . . . .
C17 C 0.6092(2) 0.5679(2) 0.79843(18) 0.0436(4) Uani 1 1 d . . . . .
H17 H 0.5630 0.5880 0.8832 0.052 Uiso 1 1 calc R U . . .
C16 C 0.5452(2) 0.6609(2) 0.68399(18) 0.0401(4) Uani 1 1 d . . . . .
C7 C 0.3982(2) 0.8471(2) 0.50438(18) 0.0403(4) Uani 1 1 d . . . . .
C5 C 0.2306(2) 1.1094(2) 0.4515(2) 0.0485(5) Uani 1 1 d . . . . .
H5 H 0.2786 1.1224 0.5026 0.058 Uiso 1 1 calc R U . . .
C20 C 0.7502(2) 0.5140(2) 0.54107(19) 0.0484(5) Uani 1 1 d . . . . .
H20 H 0.8004 0.4955 0.4557 0.058 Uiso 1 1 calc R U . . .
C18 C 0.7408(2) 0.4465(2) 0.78490(19) 0.0469(5) Uani 1 1 d . . . . .
C1 C 0.2009(2) 0.9549(2) 0.36166(19) 0.0494(5) Uani 1 1 d . . . . .
H1 H 0.2301 0.8638 0.3511 0.059 Uiso 1 1 calc R U . . .
C10 C 0.6013(2) 0.8644(2) 0.19887(19) 0.0500(5) Uani 1 1 d . . . . .
H10 H 0.5866 0.9467 0.2189 0.060 Uiso 1 1 calc R U . . .
C19 C 0.8106(2) 0.4223(2) 0.6548(2) 0.0523(5) Uani 1 1 d . . . . .
H19 H 0.9013 0.3411 0.6451 0.063 Uiso 1 1 calc R U . . .
C2 C 0.0838(2) 1.0716(3) 0.3028(2) 0.0588(6) Uani 1 1 d . . . . .
H2 H 0.0337 1.0590 0.2532 0.071 Uiso 1 1 calc R U . . .
C14 C 0.6001(3) 0.6226(3) 0.2722(2) 0.0565(5) Uani 1 1 d . . . . .
H14 H 0.5846 0.5406 0.3425 0.068 Uiso 1 1 calc R U . . .
C3 C 0.0407(2) 1.2068(3) 0.3170(2) 0.0615(6) Uani 1 1 d . . . . .
H3 H -0.0386 1.2854 0.2770 0.074 Uiso 1 1 calc R U . . .
C4 C 0.1148(2) 1.2260(2) 0.3905(2) 0.0581(5) Uani 1 1 d . . . . .
H4 H 0.0866 1.3180 0.3988 0.070 Uiso 1 1 calc R U . . .
C12 C 0.6707(3) 0.7425(3) 0.0316(2) 0.0665(7) Uani 1 1 d . . . . .
H12 H 0.7014 0.7424 -0.0603 0.080 Uiso 1 1 calc R U . . .
C11 C 0.6489(2) 0.8625(3) 0.0625(2) 0.0607(6) Uani 1 1 d . . . . .
H11 H 0.6662 0.9434 -0.0085 0.073 Uiso 1 1 calc R U . . .
C21 C 0.8089(3) 0.3418(2) 0.9091(2) 0.0604(6) Uani 1 1 d . . . . .
H21 H 0.7312 0.3715 0.9897 0.072 Uiso 1 1 calc R U . . .
C13 C 0.6471(3) 0.6221(3) 0.1361(2) 0.0701(7) Uani 1 1 d . . . . .
H13 H 0.6629 0.5401 0.1151 0.084 Uiso 1 1 calc R U . . .
C22 C 0.9568(4) 0.3597(5) 0.9019(3) 0.1290(15) Uani 1 1 d . . . . .
H22A H 0.9363 0.4607 0.8865 0.194 Uiso 1 1 calc R U . . .
H22B H 0.9891 0.3029 0.9875 0.194 Uiso 1 1 calc R U . . .
H22C H 1.0391 0.3270 0.8272 0.194 Uiso 1 1 calc R U . . .
C24 C 0.8236(6) 0.1881(3) 0.9330(3) 0.1291(16) Uani 1 1 d . . . . .
H24A H 0.7244 0.1874 0.9361 0.194 Uiso 1 1 calc R U . . .
H24B H 0.9030 0.1515 0.8590 0.194 Uiso 1 1 calc R U . . .
H24C H 0.8529 0.1274 1.0193 0.194 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 C16 1.724(2) . ?
S1 C7 1.7437(19) . ?
C9 C10 1.384(3) . ?
C9 C14 1.390(3) . ?
C9 C8 1.481(2) . ?
C8 C7 1.359(3) . ?
C8 C15 1.440(3) . ?
C15 C20 1.398(3) . ?
C15 C16 1.404(2) . ?
C6 C5 1.387(3) . ?
C6 C1 1.396(3) . ?
C6 C7 1.475(3) . ?
C17 C18 1.371(3) . ?
C17 C16 1.394(3) . ?
C17 H17 0.9300 . ?
C5 C4 1.377(3) . ?
C5 H5 0.9300 . ?
C20 C19 1.370(3) . ?
C20 H20 0.9300 . ?
C18 C19 1.399(3) . ?
C18 C21 1.514(3) . ?
C1 C2 1.375(3) . ?
C1 H1 0.9300 . ?
C10 C11 1.385(3) . ?
C10 H10 0.9300 . ?
C19 H19 0.9300 . ?
C2 C3 1.373(3) . ?
C2 H2 0.9300 . ?
C14 C13 1.378(3) . ?
C14 H14 0.9300 . ?
C3 C4 1.381(3) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C12 C11 1.366(3) . ?
C12 C13 1.372(4) . ?
C12 H12 0.9300 . ?
C11 H11 0.9300 . ?
C21 C24 1.505(4) . ?
C21 C22 1.509(4) . ?
C21 H21 0.9800 . ?
C13 H13 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
C16 S1 C7 91.81(9) . . ?
C10 C9 C14 118.56(17) . . ?
C10 C9 C8 120.92(17) . . ?
C14 C9 C8 120.52(17) . . ?
C7 C8 C15 112.33(16) . . ?
C7 C8 C9 124.79(16) . . ?
C15 C8 C9 122.85(16) . . ?
C20 C15 C16 117.68(17) . . ?
C20 C15 C8 129.95(16) . . ?
C16 C15 C8 112.36(16) . . ?
C5 C6 C1 118.87(18) . . ?
C5 C6 C7 120.36(17) . . ?
C1 C6 C7 120.74(17) . . ?
C18 C17 C16 119.42(17) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C16 C15 121.98(17) . . ?
C17 C16 S1 126.92(14) . . ?
C15 C16 S1 111.09(13) . . ?
C8 C7 C6 129.62(16) . . ?
C8 C7 S1 112.42(14) . . ?
C6 C7 S1 117.92(13) . . ?
C4 C5 C6 120.39(19) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C19 C20 C15 119.73(17) . . ?
C19 C20 H20 120.1 . . ?
C15 C20 H20 120.1 . . ?
C17 C18 C19 118.84(18) . . ?
C17 C18 C21 120.16(17) . . ?
C19 C18 C21 121.00(18) . . ?
C2 C1 C6 120.3(2) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C9 C10 C11 120.2(2) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C20 C19 C18 122.28(18) . . ?
C20 C19 H19 118.9 . . ?
C18 C19 H19 118.9 . . ?
C3 C2 C1 120.2(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C13 C14 C9 120.7(2) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
C2 C3 C4 120.1(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.1(2) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C11 C12 C13 119.9(2) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C11 C10 120.5(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C24 C21 C22 115.4(3) . . ?
C24 C21 C18 111.7(2) . . ?
C22 C21 C18 111.0(2) . . ?
C24 C21 H21 106.0 . . ?
C22 C21 H21 106.0 . . ?
C18 C21 H21 106.0 . . ?
C12 C13 C14 120.1(2) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_refine_diff_density_max         0.230
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.047



####################################################################### 
# 
# 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_RN12
_database_code_depnum_ccdc_archive 'CCDC 1479468'
_audit_update_record             
;
2016-05-12 deposited with the CCDC.
2016-07-18 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         'C20 H13 F S'
_chemical_formula_sum            'C20 H13 F S'
_chemical_formula_weight         304.36

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'

_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                   6.0606(6)
_cell_length_b                   13.4845(14)
_cell_length_c                   18.390(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.360(4)
_cell_angle_gamma                90
_cell_volume                     1502.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1676
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      24.21

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.219
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.983
_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            8823
_diffrn_reflns_av_unetI/netI     0.0881
_diffrn_reflns_av_R_equivalents  0.0749
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.682
_diffrn_reflns_theta_max         27.504
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3239
_reflns_number_gt                1829
_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)+(0.0512P)²+0.4319P] 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         3239
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1383
_refine_ls_R_factor_gt           0.0626
_refine_ls_wR_factor_ref         0.1349
_refine_ls_wR_factor_gt          0.1128
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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 0.70060(13) -0.05033(6) 0.32777(4) 0.0485(3) Uani 1 1 d . . . . .
C15 C 0.6105(4) 0.14747(19) 0.16463(14) 0.0356(6) Uani 1 1 d . . . . .
F1 F 0.0608(3) 0.10603(17) 0.46559(11) 0.0868(7) Uani 1 1 d . . . . .
C10 C 0.4898(4) 0.0318(2) 0.34552(15) 0.0409(7) Uani 1 1 d . . . . .
C17 C 0.7923(4) 0.2046(2) 0.14834(16) 0.0443(7) Uani 1 1 d . . . . .
H17 H 0.9168 0.2024 0.1789 0.053 Uiso 1 1 calc R U . . .
C7 C 0.7489(4) 0.0053(2) 0.24368(14) 0.0394(7) Uani 1 1 d . . . . .
C19 C 0.6101(6) 0.2681(2) 0.04177(17) 0.0554(8) Uani 1 1 d . . . . .
H19 H 0.6099 0.3081 0.0006 0.066 Uiso 1 1 calc R U . . .
C8 C 0.6107(4) 0.08334(19) 0.23029(15) 0.0362(7) Uani 1 1 d . . . . .
C13 C 0.1628(5) 0.1737(2) 0.35356(19) 0.0573(9) Uani 1 1 d . . . . .
H13 H 0.0524 0.2212 0.3574 0.069 Uiso 1 1 calc R U . . .
C12 C 0.1955(6) 0.1040(3) 0.40737(18) 0.0573(9) Uani 1 1 d . . . . .
C16 C 0.4270(4) 0.1520(2) 0.11806(16) 0.0470(8) Uani 1 1 d . . . . .
H16 H 0.3024 0.1144 0.1278 0.056 Uiso 1 1 calc R U . . .
C3 C 0.9195(4) -0.0389(2) 0.19800(15) 0.0389(7) Uani 1 1 d . . . . .
C9 C 0.4611(4) 0.10023(19) 0.28850(15) 0.0374(7) Uani 1 1 d . . . . .
C5 C 1.2686(5) -0.1231(2) 0.1885(2) 0.0585(9) Uani 1 1 d . . . . .
H5 H 1.3926 -0.1513 0.2109 0.070 Uiso 1 1 calc R U . . .
C11 C 0.3553(5) 0.0330(2) 0.40619(15) 0.0514(8) Uani 1 1 d . . . . .
H11 H 0.3741 -0.0123 0.4439 0.062 Uiso 1 1 calc R U . . .
C14 C 0.2952(4) 0.1724(2) 0.29418(16) 0.0458(7) Uani 1 1 d . . . . .
H14 H 0.2751 0.2193 0.2576 0.055 Uiso 1 1 calc R U . . .
C2 C 0.8987(5) -0.0416(2) 0.12237(16) 0.0479(7) Uani 1 1 d . . . . .
H2 H 0.7735 -0.0152 0.0995 0.058 Uiso 1 1 calc R U . . .
C18 C 0.7925(5) 0.2647(2) 0.08776(17) 0.0526(8) Uani 1 1 d . . . . .
H18 H 0.9158 0.3030 0.0779 0.063 Uiso 1 1 calc R U . . .
C4 C 1.1064(4) -0.0812(2) 0.23022(17) 0.0463(8) Uani 1 1 d . . . . .
H4 H 1.1226 -0.0814 0.2806 0.056 Uiso 1 1 calc R U . . .
C20 C 0.4290(5) 0.2121(2) 0.05734(17) 0.0549(9) Uani 1 1 d . . . . .
H20 H 0.3052 0.2145 0.0265 0.066 Uiso 1 1 calc R U . . .
C1 C 1.0617(5) -0.0831(2) 0.08129(18) 0.0552(9) Uani 1 1 d . . . . .
H1 H 1.0464 -0.0839 0.0309 0.066 Uiso 1 1 calc R U . . .
C6 C 1.2473(5) -0.1233(2) 0.1144(2) 0.0617(9) Uani 1 1 d . . . . .
H6 H 1.3578 -0.1504 0.0863 0.074 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 C10 1.727(3) . ?
S1 C7 1.750(3) . ?
C15 C17 1.383(4) . ?
C15 C16 1.389(3) . ?
C15 C8 1.485(4) . ?
F1 C12 1.362(4) . ?
C10 C11 1.397(4) . ?
C10 C9 1.405(4) . ?
C17 C18 1.378(4) . ?
C17 H17 0.9300 . ?
C7 C8 1.363(4) . ?
C7 C3 1.474(4) . ?
C19 C20 1.369(4) . ?
C19 C18 1.376(4) . ?
C19 H19 0.9300 . ?
C8 C9 1.437(4) . ?
C13 C14 1.370(4) . ?
C13 C12 1.376(4) . ?
C13 H13 0.9300 . ?
C12 C11 1.362(4) . ?
C16 C20 1.380(4) . ?
C16 H16 0.9300 . ?
C3 C4 1.388(4) . ?
C3 C2 1.394(4) . ?
C9 C14 1.405(4) . ?
C5 C6 1.366(5) . ?
C5 C4 1.383(4) . ?
C5 H5 0.9300 . ?
C11 H11 0.9300 . ?
C14 H14 0.9300 . ?
C2 C1 1.377(4) . ?
C2 H2 0.9300 . ?
C18 H18 0.9300 . ?
C4 H4 0.9300 . ?
C20 H20 0.9300 . ?
C1 C6 1.377(4) . ?
C1 H1 0.9300 . ?
C6 H6 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
C10 S1 C7 91.84(13) . . ?
C17 C15 C16 118.2(3) . . ?
C17 C15 C8 121.0(2) . . ?
C16 C15 C8 120.8(2) . . ?
C11 C10 C9 121.6(3) . . ?
C11 C10 S1 127.4(2) . . ?
C9 C10 S1 111.0(2) . . ?
C18 C17 C15 121.3(3) . . ?
C18 C17 H17 119.4 . . ?
C15 C17 H17 119.4 . . ?
C8 C7 C3 130.2(3) . . ?
C8 C7 S1 112.1(2) . . ?
C3 C7 S1 117.7(2) . . ?
C20 C19 C18 119.3(3) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C7 C8 C9 112.5(2) . . ?
C7 C8 C15 125.8(3) . . ?
C9 C8 C15 121.7(2) . . ?
C14 C13 C12 119.1(3) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
F1 C12 C11 117.8(3) . . ?
F1 C12 C13 118.2(3) . . ?
C11 C12 C13 124.0(3) . . ?
C20 C16 C15 120.1(3) . . ?
C20 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C4 C3 C2 117.9(3) . . ?
C4 C3 C7 120.0(2) . . ?
C2 C3 C7 122.1(2) . . ?
C14 C9 C10 118.4(3) . . ?
C14 C9 C8 129.1(3) . . ?
C10 C9 C8 112.5(2) . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C12 C11 C10 116.7(3) . . ?
C12 C11 H11 121.6 . . ?
C10 C11 H11 121.6 . . ?
C13 C14 C9 120.2(3) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
C1 C2 C3 120.6(3) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C17 C18 C19 120.0(3) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C5 C4 C3 121.0(3) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C19 C20 C16 121.1(3) . . ?
C19 C20 H20 119.5 . . ?
C16 C20 H20 119.5 . . ?
C2 C1 C6 120.5(3) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C5 C6 C1 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?

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
C7 S1 C10 C11 177.8(3) . . . . ?
C7 S1 C10 C9 -0.7(2) . . . . ?
C16 C15 C17 C18 0.1(4) . . . . ?
C8 C15 C17 C18 -179.6(3) . . . . ?
C10 S1 C7 C8 0.3(2) . . . . ?
C10 S1 C7 C3 -177.4(2) . . . . ?
C3 C7 C8 C9 177.6(3) . . . . ?
S1 C7 C8 C9 0.1(3) . . . . ?
C3 C7 C8 C15 -3.6(4) . . . . ?
S1 C7 C8 C15 178.9(2) . . . . ?
C17 C15 C8 C7 -62.5(4) . . . . ?
C16 C15 C8 C7 117.8(3) . . . . ?
C17 C15 C8 C9 116.2(3) . . . . ?
C16 C15 C8 C9 -63.5(4) . . . . ?
C14 C13 C12 F1 -179.4(3) . . . . ?
C14 C13 C12 C11 0.9(5) . . . . ?
C17 C15 C16 C20 0.1(4) . . . . ?
C8 C15 C16 C20 179.8(3) . . . . ?
C8 C7 C3 C4 148.3(3) . . . . ?
S1 C7 C3 C4 -34.3(3) . . . . ?
C8 C7 C3 C2 -32.8(4) . . . . ?
S1 C7 C3 C2 144.5(2) . . . . ?
C11 C10 C9 C14 1.2(4) . . . . ?
S1 C10 C9 C14 179.81(19) . . . . ?
C11 C10 C9 C8 -177.7(2) . . . . ?
S1 C10 C9 C8 0.9(3) . . . . ?
C7 C8 C9 C14 -179.4(3) . . . . ?
C15 C8 C9 C14 1.7(4) . . . . ?
C7 C8 C9 C10 -0.7(3) . . . . ?
C15 C8 C9 C10 -179.5(2) . . . . ?
F1 C12 C11 C10 179.3(3) . . . . ?
C13 C12 C11 C10 -1.0(5) . . . . ?
C9 C10 C11 C12 -0.1(4) . . . . ?
S1 C10 C11 C12 -178.5(2) . . . . ?
C12 C13 C14 C9 0.3(4) . . . . ?
C10 C9 C14 C13 -1.3(4) . . . . ?
C8 C9 C14 C13 177.4(3) . . . . ?
C4 C3 C2 C1 -1.5(4) . . . . ?
C7 C3 C2 C1 179.7(3) . . . . ?
C15 C17 C18 C19 -0.5(5) . . . . ?
C20 C19 C18 C17 0.6(5) . . . . ?
C6 C5 C4 C3 0.2(5) . . . . ?
C2 C3 C4 C5 1.2(4) . . . . ?
C7 C3 C4 C5 -180.0(3) . . . . ?
C18 C19 C20 C16 -0.3(5) . . . . ?
C15 C16 C20 C19 0.0(5) . . . . ?
C3 C2 C1 C6 0.5(4) . . . . ?
C4 C5 C6 C1 -1.1(5) . . . . ?
C2 C1 C6 C5 0.8(5) . . . . ?

_refine_diff_density_max         0.194
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.049



