# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_mo_d8v17408_0m
_database_code_depnum_ccdc_archive 'CCDC 1576900'
_audit_update_record             
;
2017-12-21 deposited with the CCDC.
2018-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H15 Cl O'
_chemical_formula_weight         258.73

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 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+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   57.5837(19)
_cell_length_b                   5.8021(2)
_cell_length_c                   8.0527(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2690.46(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9901
_cell_measurement_theta_min      4.952
_cell_measurement_theta_max      46.290

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.269
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5892
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_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            74652
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_av_R_equivalents  0.0886
_diffrn_reflns_limit_h_min       -64
_diffrn_reflns_limit_h_max       64
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.830
_diffrn_reflns_theta_max         23.367
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.811
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.811
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.811
_reflns_number_total             1959
_reflns_number_gt                1676
_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-2013 (Sheldrick, 2013)'
_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)+(0.0439P)²+2.2919P] 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     SHELXL
_refine_ls_extinction_coef       0.0060(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1959
_refine_ls_number_parameters     165
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1297
_refine_ls_wR_factor_gt          0.1230
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.57415(2) 0.4832(2) 0.67384(15) 0.1100(5) Uani 1 1 d . . . . .
O1 O 0.50386(3) 0.7987(5) 0.5822(4) 0.1007(9) Uani 1 1 d D . . . .
H1 H 0.5051 0.9304 0.6179 0.151 Uiso 1 1 calc DR U . . .
C1 C 0.68997(5) 0.9061(5) 0.1818(4) 0.0700(9) Uani 1 1 d . . . . .
H1A H 0.6805 1.0188 0.1351 0.084 Uiso 1 1 calc R U . . .
C2 C 0.71303(5) 0.8931(6) 0.1344(4) 0.0786(9) Uani 1 1 d . . . . .
H2 H 0.7189 0.9968 0.0568 0.094 Uiso 1 1 calc R U . . .
C3 C 0.72723(5) 0.7302(6) 0.2002(4) 0.0725(9) Uani 1 1 d . . . . .
H3 H 0.7427 0.7216 0.1683 0.087 Uiso 1 1 calc R U . . .
C4 C 0.71848(5) 0.5803(6) 0.3129(4) 0.0844(11) Uani 1 1 d . . . . .
H4 H 0.7281 0.4678 0.3582 0.101 Uiso 1 1 calc R U . . .
C5 C 0.69540(5) 0.5920(6) 0.3616(4) 0.0761(9) Uani 1 1 d . . . . .
H5 H 0.6898 0.4876 0.4394 0.091 Uiso 1 1 calc R U . . .
C6 C 0.68071(4) 0.7561(5) 0.2965(3) 0.0518(7) Uani 1 1 d . . . . .
C7 C 0.65595(4) 0.7759(5) 0.3518(3) 0.0503(6) Uani 1 1 d . . . . .
C8 C 0.64499(4) 0.6060(5) 0.4431(4) 0.0621(8) Uani 1 1 d . . . . .
H8 H 0.6532 0.4736 0.4705 0.075 Uiso 1 1 calc R U . . .
C9 C 0.62219(4) 0.6261(5) 0.4952(4) 0.0638(8) Uani 1 1 d . . . . .
H9 H 0.6154 0.5072 0.5557 0.077 Uiso 1 1 calc R U . . .
C10 C 0.60928(4) 0.8215(5) 0.4583(3) 0.0519(7) Uani 1 1 d . . . . .
C11 C 0.62026(5) 0.9917(5) 0.3673(4) 0.0649(8) Uani 1 1 d . . . . .
H11 H 0.6121 1.1247 0.3403 0.078 Uiso 1 1 calc R U . . .
C12 C 0.64299(5) 0.9703(5) 0.3154(4) 0.0663(8) Uani 1 1 d . . . . .
H12 H 0.6497 1.0890 0.2546 0.080 Uiso 1 1 calc R U . . .
C13 C 0.58515(4) 0.8681(5) 0.5081(4) 0.0614(8) Uani 1 1 d . . . . .
H13 H 0.5800 1.0118 0.4727 0.074 Uiso 1 1 calc R U . . .
C14 C 0.56912(4) 0.7535(5) 0.5914(4) 0.0611(8) Uani 1 1 d . . . . .
C15 C 0.54528(5) 0.8409(6) 0.6299(4) 0.0731(9) Uani 1 1 d . . . . .
H15A H 0.5444 1.0020 0.5983 0.088 Uiso 1 1 calc R U . . .
H15B H 0.5428 0.8317 0.7488 0.088 Uiso 1 1 calc R U . . .
C16 C 0.52626(4) 0.7105(6) 0.5430(5) 0.0827(10) Uani 1 1 d . . . . .
H16A H 0.5287 0.7196 0.4239 0.099 Uiso 1 1 calc R U . . .
H16B H 0.5270 0.5494 0.5748 0.099 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
Cl1 C14 1.728(3) . ?
O1 C16 1.423(3) . ?
O1 H1 0.8200 . ?
C1 C6 1.377(4) . ?
C1 C2 1.384(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.357(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.354(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.498(3) . ?
C7 C8 1.382(4) . ?
C7 C12 1.384(4) . ?
C8 C9 1.383(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.388(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.382(4) . ?
C10 C13 1.472(3) . ?
C11 C12 1.379(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.320(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.496(4) . ?
C15 C16 1.504(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?

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 O1 H1 109.5 . . ?
C6 C1 C2 121.5(3) . . ?
C6 C1 H1A 119.3 . . ?
C2 C1 H1A 119.3 . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 119.0(3) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 121.0(3) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C1 C6 C5 117.0(2) . . ?
C1 C6 C7 121.3(2) . . ?
C5 C6 C7 121.7(2) . . ?
C8 C7 C12 116.6(2) . . ?
C8 C7 C6 122.5(2) . . ?
C12 C7 C6 120.9(2) . . ?
C7 C8 C9 122.3(3) . . ?
C7 C8 H8 118.8 . . ?
C9 C8 H8 118.8 . . ?
C8 C9 C10 120.8(3) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 116.9(2) . . ?
C11 C10 C13 116.4(2) . . ?
C9 C10 C13 126.7(3) . . ?
C12 C11 C10 122.0(3) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C7 121.4(3) . . ?
C11 C12 H12 119.3 . . ?
C7 C12 H12 119.3 . . ?
C14 C13 C10 134.9(3) . . ?
C14 C13 H13 112.5 . . ?
C10 C13 H13 112.5 . . ?
C13 C14 C15 125.2(3) . . ?
C13 C14 Cl1 122.4(2) . . ?
C15 C14 Cl1 112.4(2) . . ?
C14 C15 C16 113.7(3) . . ?
C14 C15 H15A 108.8 . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15B 108.8 . . ?
C16 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
O1 C16 C15 112.1(3) . . ?
O1 C16 H16A 109.2 . . ?
C15 C16 H16A 109.2 . . ?
O1 C16 H16B 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?

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(5) . . . . ?
C1 C2 C3 C4 0.1(5) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C3 C4 C5 C6 0.2(6) . . . . ?
C2 C1 C6 C5 -0.2(5) . . . . ?
C2 C1 C6 C7 177.9(3) . . . . ?
C4 C5 C6 C1 0.0(5) . . . . ?
C4 C5 C6 C7 -178.0(3) . . . . ?
C1 C6 C7 C8 168.2(3) . . . . ?
C5 C6 C7 C8 -13.8(4) . . . . ?
C1 C6 C7 C12 -12.9(4) . . . . ?
C5 C6 C7 C12 165.1(3) . . . . ?
C12 C7 C8 C9 0.5(4) . . . . ?
C6 C7 C8 C9 179.4(3) . . . . ?
C7 C8 C9 C10 -0.5(5) . . . . ?
C8 C9 C10 C11 0.3(4) . . . . ?
C8 C9 C10 C13 -178.7(3) . . . . ?
C9 C10 C11 C12 -0.1(4) . . . . ?
C13 C10 C11 C12 179.0(3) . . . . ?
C10 C11 C12 C7 0.1(5) . . . . ?
C8 C7 C12 C11 -0.3(4) . . . . ?
C6 C7 C12 C11 -179.2(3) . . . . ?
C11 C10 C13 C14 179.3(3) . . . . ?
C9 C10 C13 C14 -1.7(5) . . . . ?
C10 C13 C14 C15 178.9(3) . . . . ?
C10 C13 C14 Cl1 0.8(5) . . . . ?
C13 C14 C15 C16 113.2(4) . . . . ?
Cl1 C14 C15 C16 -68.6(3) . . . . ?
C14 C15 C16 O1 -179.9(3) . . . . ?

_refine_diff_density_max         0.376
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.037

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_d8v17669
_database_code_depnum_ccdc_archive 'CCDC 1588850'
_audit_update_record             
;
2017-12-04 deposited with the CCDC.
2018-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H13 F3 O2 S'
_chemical_formula_weight         278.28

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'
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      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                   10.0641(3)
_cell_length_b                   10.4692(2)
_cell_length_c                   12.4244(3)
_cell_angle_alpha                90.0330(10)
_cell_angle_beta                 93.7370(10)
_cell_angle_gamma                96.6490(10)
_cell_volume                     1297.46(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9403
_cell_measurement_theta_min      5.071
_cell_measurement_theta_max      54.678

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.277
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6808
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_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            22587
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.535
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             5066
_reflns_number_gt                4064
_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-2013 (Sheldrick, 2013)'
_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)+(0.0649P)²+0.2928P] 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     SHELXL
_refine_ls_extinction_coef       0.118(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5066
_refine_ls_number_parameters     330
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.1252
_refine_ls_wR_factor_gt          0.1119
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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 0.65478(5) 0.80520(5) 0.31706(4) 0.05940(19) Uani 1 1 d . . . . .
S2 S 0.70674(6) 0.70892(5) 0.82119(4) 0.06332(19) Uani 1 1 d . . . . .
F1 F 0.6100(2) 1.04604(13) 0.30363(13) 0.1050(6) Uani 1 1 d . . . . .
F2 F 0.6675(2) 0.96250(15) 0.16205(12) 0.1080(6) Uani 1 1 d . . . . .
F3 F 0.4702(2) 0.91762(18) 0.20832(16) 0.1177(6) Uani 1 1 d . . . . .
F4 F 0.66210(19) 0.73852(14) 1.02359(11) 0.0941(5) Uani 1 1 d . . . . .
F5 F 0.5392(2) 0.83842(17) 0.91774(16) 0.1125(6) Uani 1 1 d . . . . .
F6 F 0.7444(2) 0.90580(15) 0.94255(15) 0.1185(6) Uani 1 1 d . . . . .
O1 O 0.36966(15) 0.59368(14) 0.43695(12) 0.0660(4) Uani 1 1 d . . . . .
H1 H 0.4282 0.5623 0.4064 0.099 Uiso 1 1 calc R U . . .
O2 O 0.82789(15) 0.98618(15) 0.66035(13) 0.0698(4) Uani 1 1 d . . . . .
O3 O 0.42292(19) 0.52310(16) 0.64649(13) 0.0783(5) Uani 1 1 d . . . . .
H3 H 0.4021 0.5559 0.5888 0.117 Uiso 1 1 calc R U . . .
O4 O 0.79289(15) 0.31397(15) 1.00745(13) 0.0706(4) Uani 1 1 d . . . . .
C1 C 0.58537(18) 0.81947(17) 0.44435(14) 0.0475(4) Uani 1 1 d . . . . .
C2 C 0.43637(18) 0.82526(19) 0.44621(16) 0.0546(5) Uani 1 1 d . . . . .
H2A H 0.4151 0.9044 0.4122 0.066 Uiso 1 1 calc R U . . .
H2B H 0.4135 0.8286 0.5207 0.066 Uiso 1 1 calc R U . . .
C3 C 0.35000(19) 0.71387(19) 0.39047(16) 0.0547(5) Uani 1 1 d . . . . .
H3A H 0.2565 0.7272 0.3934 0.066 Uiso 1 1 calc R U . . .
H3B H 0.3698 0.7122 0.3151 0.066 Uiso 1 1 calc R U . . .
C4 C 0.66400(18) 0.81817(18) 0.53359(15) 0.0506(4) Uani 1 1 d . . . . .
H4 H 0.6221 0.8254 0.5975 0.061 Uiso 1 1 calc R U . . .
C5 C 0.80930(18) 0.80690(18) 0.54626(15) 0.0510(4) Uani 1 1 d . . . . .
C6 C 0.8661(2) 0.7093(2) 0.49775(18) 0.0619(5) Uani 1 1 d . . . . .
H6 H 0.8122 0.6497 0.4538 0.074 Uiso 1 1 calc R U . . .
C7 C 1.0021(2) 0.6988(2) 0.5135(2) 0.0737(6) Uani 1 1 d . . . . .
H7 H 1.0391 0.6327 0.4806 0.088 Uiso 1 1 calc R U . . .
C8 C 1.0815(2) 0.7870(3) 0.5784(2) 0.0774(7) Uani 1 1 d . . . . .
H8 H 1.1728 0.7806 0.5887 0.093 Uiso 1 1 calc R U . . .
C9 C 1.0280(2) 0.8846(2) 0.62814(19) 0.0704(6) Uani 1 1 d . . . . .
H9 H 1.0831 0.9441 0.6714 0.084 Uiso 1 1 calc R U . . .
C10 C 0.89129(19) 0.89446(19) 0.61376(16) 0.0557(5) Uani 1 1 d . . . . .
C11 C 0.9050(3) 1.0755(3) 0.7331(2) 0.0874(8) Uani 1 1 d . . . . .
H11A H 0.9466 1.0296 0.7905 0.131 Uiso 1 1 calc R U . . .
H11B H 0.8474 1.1316 0.7627 0.131 Uiso 1 1 calc R U . . .
H11C H 0.9729 1.1255 0.6953 0.131 Uiso 1 1 calc R U . . .
C12 C 0.5969(3) 0.9384(2) 0.24709(18) 0.0694(6) Uani 1 1 d . . . . .
C13 C 0.60872(19) 0.55869(19) 0.84237(14) 0.0507(4) Uani 1 1 d . . . . .
C14 C 0.45835(19) 0.5563(2) 0.83714(17) 0.0592(5) Uani 1 1 d . . . . .
H14A H 0.4344 0.6086 0.8957 0.071 Uiso 1 1 calc R U . . .
H14B H 0.4186 0.4687 0.8481 0.071 Uiso 1 1 calc R U . . .
C15 C 0.3991(2) 0.6043(2) 0.73196(17) 0.0608(5) Uani 1 1 d . . . . .
H15A H 0.3034 0.6059 0.7360 0.073 Uiso 1 1 calc R U . . .
H15B H 0.4393 0.6913 0.7191 0.073 Uiso 1 1 calc R U . . .
C16 C 0.66929(18) 0.45300(19) 0.85576(14) 0.0510(4) Uani 1 1 d . . . . .
H16 H 0.6134 0.3785 0.8695 0.061 Uiso 1 1 calc R U . . .
C17 C 0.81221(18) 0.43741(18) 0.85186(15) 0.0516(4) Uani 1 1 d . . . . .
C18 C 0.8876(2) 0.4883(2) 0.76826(17) 0.0605(5) Uani 1 1 d . . . . .
H18 H 0.8481 0.5372 0.7153 0.073 Uiso 1 1 calc R U . . .
C19 C 1.0201(2) 0.4670(2) 0.7630(2) 0.0726(6) Uani 1 1 d . . . . .
H19 H 1.0694 0.5013 0.7069 0.087 Uiso 1 1 calc R U . . .
C20 C 1.0780(2) 0.3953(3) 0.8409(2) 0.0779(7) Uani 1 1 d . . . . .
H20 H 1.1674 0.3819 0.8378 0.094 Uiso 1 1 calc R U . . .
C21 C 1.0059(2) 0.3423(2) 0.9238(2) 0.0705(6) Uani 1 1 d . . . . .
H21 H 1.0465 0.2935 0.9761 0.085 Uiso 1 1 calc R U . . .
C22 C 0.8731(2) 0.36206(19) 0.92918(16) 0.0564(5) Uani 1 1 d . . . . .
C23 C 0.8456(3) 0.2301(3) 1.0847(2) 0.0918(8) Uani 1 1 d . . . . .
H23A H 0.8759 0.1590 1.0483 0.138 Uiso 1 1 calc R U . . .
H23B H 0.7770 0.1985 1.1314 0.138 Uiso 1 1 calc R U . . .
H23C H 0.9195 0.2759 1.1267 0.138 Uiso 1 1 calc R U . . .
C24 C 0.6603(3) 0.8001(2) 0.93064(19) 0.0719(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 C12 1.779(2) . ?
S1 C1 1.7830(18) . ?
S2 C24 1.779(2) . ?
S2 C13 1.7864(19) . ?
F1 C12 1.317(3) . ?
F2 C12 1.320(3) . ?
F3 C12 1.327(3) . ?
F4 C24 1.323(3) . ?
F5 C24 1.327(3) . ?
F6 C24 1.316(3) . ?
O1 C3 1.414(2) . ?
O1 H1 0.8200 . ?
O2 C10 1.361(2) . ?
O2 C11 1.426(3) . ?
O3 C15 1.410(3) . ?
O3 H3 0.8200 . ?
O4 C22 1.364(3) . ?
O4 C23 1.421(3) . ?
C1 C4 1.321(3) . ?
C1 C2 1.509(3) . ?
C2 C3 1.510(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.479(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(3) . ?
C5 C10 1.399(3) . ?
C6 C7 1.387(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.372(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.373(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.391(3) . ?
C9 H9 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 C16 1.329(3) . ?
C13 C14 1.508(3) . ?
C14 C15 1.512(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.470(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.396(3) . ?
C17 C22 1.399(3) . ?
C18 C19 1.383(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.367(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.379(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.381(3) . ?
C21 H21 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
C12 S1 C1 101.22(10) . . ?
C24 S2 C13 100.17(10) . . ?
C3 O1 H1 109.5 . . ?
C10 O2 C11 118.17(18) . . ?
C15 O3 H3 109.5 . . ?
C22 O4 C23 118.15(19) . . ?
C4 C1 C2 122.21(16) . . ?
C4 C1 S1 119.31(14) . . ?
C2 C1 S1 118.39(13) . . ?
C1 C2 C3 114.74(15) . . ?
C1 C2 H2A 108.6 . . ?
C3 C2 H2A 108.6 . . ?
C1 C2 H2B 108.6 . . ?
C3 C2 H2B 108.6 . . ?
H2A C2 H2B 107.6 . . ?
O1 C3 C2 113.07(16) . . ?
O1 C3 H3A 109.0 . . ?
C2 C3 H3A 109.0 . . ?
O1 C3 H3B 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C1 C4 C5 129.14(17) . . ?
C1 C4 H4 115.4 . . ?
C5 C4 H4 115.4 . . ?
C6 C5 C10 118.76(18) . . ?
C6 C5 C4 122.34(17) . . ?
C10 C5 C4 118.84(17) . . ?
C5 C6 C7 121.1(2) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C6 119.3(2) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C9 121.0(2) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C8 C9 C10 119.9(2) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
O2 C10 C9 124.70(19) . . ?
O2 C10 C5 115.43(17) . . ?
C9 C10 C5 119.9(2) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
F1 C12 F2 106.14(18) . . ?
F1 C12 F3 107.3(2) . . ?
F2 C12 F3 105.3(2) . . ?
F1 C12 S1 114.54(17) . . ?
F2 C12 S1 108.87(18) . . ?
F3 C12 S1 113.99(16) . . ?
C16 C13 C14 122.55(17) . . ?
C16 C13 S2 119.46(15) . . ?
C14 C13 S2 117.87(14) . . ?
C13 C14 C15 114.07(16) . . ?
C13 C14 H14A 108.7 . . ?
C15 C14 H14A 108.7 . . ?
C13 C14 H14B 108.7 . . ?
C15 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
O3 C15 C14 109.81(17) . . ?
O3 C15 H15A 109.7 . . ?
C14 C15 H15A 109.7 . . ?
O3 C15 H15B 109.7 . . ?
C14 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
C13 C16 C17 129.06(18) . . ?
C13 C16 H16 115.5 . . ?
C17 C16 H16 115.5 . . ?
C18 C17 C22 118.40(18) . . ?
C18 C17 C16 121.74(18) . . ?
C22 C17 C16 119.70(17) . . ?
C19 C18 C17 120.9(2) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C20 C19 C18 119.5(2) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C21 121.1(2) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C20 C21 C22 119.9(2) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
O4 C22 C21 124.6(2) . . ?
O4 C22 C17 115.15(18) . . ?
C21 C22 C17 120.3(2) . . ?
O4 C23 H23A 109.5 . . ?
O4 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O4 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
F6 C24 F4 107.7(2) . . ?
F6 C24 F5 105.8(2) . . ?
F4 C24 F5 105.4(2) . . ?
F6 C24 S2 108.86(18) . . ?
F4 C24 S2 113.64(16) . . ?
F5 C24 S2 114.93(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 S1 C1 C4 -128.95(17) . . . . ?
C12 S1 C1 C2 54.39(17) . . . . ?
C4 C1 C2 C3 -121.0(2) . . . . ?
S1 C1 C2 C3 55.5(2) . . . . ?
C1 C2 C3 O1 60.7(2) . . . . ?
C2 C1 C4 C5 176.94(18) . . . . ?
S1 C1 C4 C5 0.4(3) . . . . ?
C1 C4 C5 C6 -52.2(3) . . . . ?
C1 C4 C5 C10 130.9(2) . . . . ?
C10 C5 C6 C7 -1.1(3) . . . . ?
C4 C5 C6 C7 -178.1(2) . . . . ?
C5 C6 C7 C8 -0.1(4) . . . . ?
C6 C7 C8 C9 0.4(4) . . . . ?
C7 C8 C9 C10 0.5(4) . . . . ?
C11 O2 C10 C9 -3.0(3) . . . . ?
C11 O2 C10 C5 177.8(2) . . . . ?
C8 C9 C10 O2 179.1(2) . . . . ?
C8 C9 C10 C5 -1.7(3) . . . . ?
C6 C5 C10 O2 -178.71(18) . . . . ?
C4 C5 C10 O2 -1.7(3) . . . . ?
C6 C5 C10 C9 2.0(3) . . . . ?
C4 C5 C10 C9 179.09(18) . . . . ?
C1 S1 C12 F1 44.9(2) . . . . ?
C1 S1 C12 F2 163.57(16) . . . . ?
C1 S1 C12 F3 -79.19(19) . . . . ?
C24 S2 C13 C16 -122.37(17) . . . . ?
C24 S2 C13 C14 61.47(17) . . . . ?
C16 C13 C14 C15 -119.1(2) . . . . ?
S2 C13 C14 C15 57.0(2) . . . . ?
C13 C14 C15 O3 63.4(2) . . . . ?
C14 C13 C16 C17 173.33(18) . . . . ?
S2 C13 C16 C17 -2.6(3) . . . . ?
C13 C16 C17 C18 -47.8(3) . . . . ?
C13 C16 C17 C22 136.9(2) . . . . ?
C22 C17 C18 C19 -1.3(3) . . . . ?
C16 C17 C18 C19 -176.65(19) . . . . ?
C17 C18 C19 C20 -0.1(3) . . . . ?
C18 C19 C20 C21 0.8(4) . . . . ?
C19 C20 C21 C22 -0.2(4) . . . . ?
C23 O4 C22 C21 -4.8(3) . . . . ?
C23 O4 C22 C17 176.1(2) . . . . ?
C20 C21 C22 O4 179.8(2) . . . . ?
C20 C21 C22 C17 -1.2(3) . . . . ?
C18 C17 C22 O4 -179.03(17) . . . . ?
C16 C17 C22 O4 -3.6(3) . . . . ?
C18 C17 C22 C21 1.9(3) . . . . ?
C16 C17 C22 C21 177.35(18) . . . . ?
C13 S2 C24 F6 166.40(17) . . . . ?
C13 S2 C24 F4 46.3(2) . . . . ?
C13 S2 C24 F5 -75.23(19) . . . . ?

_refine_diff_density_max         0.336
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.038

_shelxl_version_number           2013-4



