# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 2325011'
loop_
_audit_author_name
_audit_author_address
'Hua Xiao'
;Hefei University of Technology
China
;
_audit_update_record             
;
2024-01-12 deposited with the CCDC.	2024-04-29 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 H16 F N O2'
_chemical_formula_weight         273.30

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'
N N 0.0061 0.0033 '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'

_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                   6.463(3)
_cell_length_b                   8.279(4)
_cell_length_c                   13.176(7)
_cell_angle_alpha                103.433(13)
_cell_angle_beta                 92.304(14)
_cell_angle_gamma                92.979(14)
_cell_volume                     683.8(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2394
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      22.77

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             288
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_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  ccd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8487
_diffrn_reflns_av_unetI/netI     0.0827
_diffrn_reflns_av_R_equivalents  0.0681
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.534
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             2367
_reflns_number_gt                1303
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1894P)²+0.0280P] 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         2367
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1617
_refine_ls_R_factor_gt           0.0967
_refine_ls_wR_factor_ref         0.3046
_refine_ls_wR_factor_gt          0.2646
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7692(6) 0.6310(6) 0.9919(3) 0.0613(13) Uani 1 1 d . . . . .
H1 H 0.8153 0.5722 1.0397 0.074 Uiso 1 1 calc R U . . .
C2 C 0.7804(7) 0.8024(6) 1.0180(3) 0.0625(13) Uani 1 1 d . . . . .
C3 C 0.7175(7) 0.8945(6) 0.9506(4) 0.0665(13) Uani 1 1 d . . . . .
H3 H 0.7302 1.0102 0.9695 0.080 Uiso 1 1 calc R U . . .
C4 C 0.6346(6) 0.8113(5) 0.8536(3) 0.0555(12) Uani 1 1 d . . . . .
H4 H 0.5888 0.8722 0.8069 0.067 Uiso 1 1 calc R U . . .
C5 C 0.6175(5) 0.6384(5) 0.8236(3) 0.0469(11) Uani 1 1 d . . . . .
C6 C 0.6887(6) 0.5473(5) 0.8938(3) 0.0493(11) Uani 1 1 d . . . . .
C7 C 0.6920(7) 0.3594(5) 0.8605(3) 0.0577(12) Uani 1 1 d . . . . .
H7A H 0.6356 0.3113 0.9148 0.069 Uiso 1 1 calc R U . . .
H7B H 0.8347 0.3294 0.8532 0.069 Uiso 1 1 calc R U . . .
C8 C 0.5690(7) 0.2859(5) 0.7583(3) 0.0545(11) Uani 1 1 d . . . . .
H8A H 0.6057 0.1726 0.7306 0.065 Uiso 1 1 calc R U . . .
H8B H 0.4217 0.2837 0.7700 0.065 Uiso 1 1 calc R U . . .
C9 C 0.5257(6) 0.5500(5) 0.7169(3) 0.0441(10) Uani 1 1 d . . . . .
H9 H 0.5687 0.6167 0.6680 0.053 Uiso 1 1 calc R U . . .
C10 C 0.2888(6) 0.5333(5) 0.7095(3) 0.0472(11) Uani 1 1 d . . . . .
C11 C 0.1970(6) 0.4098(5) 0.6192(3) 0.0520(11) Uani 1 1 d . . . . .
H11 H 0.0539 0.4026 0.6062 0.062 Uiso 1 1 calc R U . . .
C12 C 0.3117(6) 0.3070(5) 0.5547(3) 0.0498(11) Uani 1 1 d . . . . .
C13 C 0.5421(6) 0.3061(6) 0.5759(3) 0.0572(12) Uani 1 1 d . . . . .
H13A H 0.5809 0.1916 0.5606 0.069 Uiso 1 1 calc R U . . .
H13B H 0.6127 0.3616 0.5286 0.069 Uiso 1 1 calc R U . . .
C14 C 0.2237(8) 0.1862(5) 0.4595(3) 0.0553(11) Uani 1 1 d . . . . .
C15 C -0.0786(9) 0.0618(7) 0.3579(4) 0.0833(16) Uani 1 1 d . . . . .
H15A H -0.0329 0.0918 0.2959 0.125 Uiso 1 1 calc R U . . .
H15B H -0.2268 0.0643 0.3591 0.125 Uiso 1 1 calc R U . . .
H15C H -0.0388 -0.0483 0.3581 0.125 Uiso 1 1 calc R U . . .
C16 C 0.1681(7) 0.6209(6) 0.7780(4) 0.0642(13) Uani 1 1 d . . . . .
H16A H 0.0246 0.6036 0.7685 0.077 Uiso 1 1 calc R U . . .
H16B H 0.2270 0.6995 0.8355 0.077 Uiso 1 1 calc R U . . .
F1 F 0.8597(5) 0.8827(4) 1.1151(2) 0.0937(11) Uani 1 1 d . . . . .
N1 N 0.6150(5) 0.3871(4) 0.6836(3) 0.0496(9) Uani 1 1 d . . . . .
O1 O 0.3287(6) 0.1027(4) 0.3976(2) 0.0757(11) Uani 1 1 d . . . . .
O2 O 0.0161(5) 0.1785(4) 0.4490(2) 0.0728(10) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.377(7) . ?
C1 C6 1.383(6) . ?
C1 H1 0.9300 . ?
C2 F1 1.363(5) . ?
C2 C3 1.362(7) . ?
C3 C4 1.376(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.401(6) . ?
C5 C9 1.508(5) . ?
C6 C7 1.517(6) . ?
C7 C8 1.516(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N1 1.463(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N1 1.473(5) . ?
C9 C10 1.527(5) . ?
C9 H9 0.9800 . ?
C10 C16 1.327(5) . ?
C10 C11 1.459(6) . ?
C11 C12 1.333(6) . ?
C11 H11 0.9300 . ?
C12 C14 1.483(6) . ?
C12 C13 1.505(6) . ?
C13 N1 1.469(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 O1 1.198(5) . ?
C14 O2 1.340(5) . ?
C15 O2 1.446(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9300 . ?
C16 H16B 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
C2 C1 C6 119.3(4) . . ?
C2 C1 H1 120.4 . . ?
C6 C1 H1 120.4 . . ?
F1 C2 C3 118.8(4) . . ?
F1 C2 C1 118.5(5) . . ?
C3 C2 C1 122.8(4) . . ?
C2 C3 C4 118.0(4) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 H3 121.0 . . ?
C3 C4 C5 121.6(4) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C4 C5 C6 119.0(4) . . ?
C4 C5 C9 120.7(4) . . ?
C6 C5 C9 120.4(4) . . ?
C1 C6 C5 119.4(4) . . ?
C1 C6 C7 120.0(4) . . ?
C5 C6 C7 120.5(4) . . ?
C6 C7 C8 112.9(3) . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
N1 C8 C7 109.2(3) . . ?
N1 C8 H8A 109.8 . . ?
C7 C8 H8A 109.8 . . ?
N1 C8 H8B 109.8 . . ?
C7 C8 H8B 109.8 . . ?
H8A C8 H8B 108.3 . . ?
N1 C9 C5 109.7(3) . . ?
N1 C9 C10 111.6(3) . . ?
C5 C9 C10 113.9(3) . . ?
N1 C9 H9 107.1 . . ?
C5 C9 H9 107.1 . . ?
C10 C9 H9 107.1 . . ?
C16 C10 C11 120.2(4) . . ?
C16 C10 C9 124.8(4) . . ?
C11 C10 C9 115.0(3) . . ?
C12 C11 C10 122.1(4) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C14 123.2(4) . . ?
C11 C12 C13 121.1(4) . . ?
C14 C12 C13 115.7(4) . . ?
N1 C13 C12 114.3(3) . . ?
N1 C13 H13A 108.7 . . ?
C12 C13 H13A 108.7 . . ?
N1 C13 H13B 108.7 . . ?
C12 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
O1 C14 O2 123.0(4) . . ?
O1 C14 C12 123.1(4) . . ?
O2 C14 C12 114.0(4) . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10 C16 H16A 120.0 . . ?
C10 C16 H16B 120.0 . . ?
H16A C16 H16B 120.0 . . ?
C8 N1 C13 113.2(3) . . ?
C8 N1 C9 109.7(3) . . ?
C13 N1 C9 110.4(3) . . ?
C14 O2 C15 116.4(4) . . ?

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 F1 179.9(3) . . . . ?
C6 C1 C2 C3 -0.8(7) . . . . ?
F1 C2 C3 C4 -178.9(3) . . . . ?
C1 C2 C3 C4 1.8(7) . . . . ?
C2 C3 C4 C5 -1.0(6) . . . . ?
C3 C4 C5 C6 -0.7(6) . . . . ?
C3 C4 C5 C9 179.9(3) . . . . ?
C2 C1 C6 C5 -0.9(6) . . . . ?
C2 C1 C6 C7 174.8(4) . . . . ?
C4 C5 C6 C1 1.6(5) . . . . ?
C9 C5 C6 C1 -178.9(3) . . . . ?
C4 C5 C6 C7 -174.1(4) . . . . ?
C9 C5 C6 C7 5.4(5) . . . . ?
C1 C6 C7 C8 171.1(3) . . . . ?
C5 C6 C7 C8 -13.2(5) . . . . ?
C6 C7 C8 N1 43.9(4) . . . . ?
C4 C5 C9 N1 151.7(3) . . . . ?
C6 C5 C9 N1 -27.8(4) . . . . ?
C4 C5 C9 C10 -82.5(4) . . . . ?
C6 C5 C9 C10 98.1(4) . . . . ?
N1 C9 C10 C16 141.5(4) . . . . ?
C5 C9 C10 C16 16.7(6) . . . . ?
N1 C9 C10 C11 -38.3(4) . . . . ?
C5 C9 C10 C11 -163.1(3) . . . . ?
C16 C10 C11 C12 -172.7(4) . . . . ?
C9 C10 C11 C12 7.1(6) . . . . ?
C10 C11 C12 C14 -176.9(3) . . . . ?
C10 C11 C12 C13 3.8(6) . . . . ?
C11 C12 C13 N1 16.9(6) . . . . ?
C14 C12 C13 N1 -162.4(3) . . . . ?
C11 C12 C14 O1 174.2(4) . . . . ?
C13 C12 C14 O1 -6.5(6) . . . . ?
C11 C12 C14 O2 -5.8(6) . . . . ?
C13 C12 C14 O2 173.5(3) . . . . ?
C7 C8 N1 C13 166.7(3) . . . . ?
C7 C8 N1 C9 -69.5(4) . . . . ?
C12 C13 N1 C8 75.8(4) . . . . ?
C12 C13 N1 C9 -47.6(4) . . . . ?
C5 C9 N1 C8 59.9(4) . . . . ?
C10 C9 N1 C8 -67.3(4) . . . . ?
C5 C9 N1 C13 -174.7(3) . . . . ?
C10 C9 N1 C13 58.2(4) . . . . ?
O1 C14 O2 C15 0.4(6) . . . . ?
C12 C14 O2 C15 -179.5(4) . . . . ?

_refine_diff_density_max         0.337
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.073



####################################################################### 
# 
# 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_1_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2325015'
loop_
_audit_author_name
_audit_author_address
'Hua Xiao'
;Hefei university of technology
China
;
_audit_update_record             
;
2024-01-12 deposited with the CCDC.	2024-04-29 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            'C17 H16 F N O6 S'
_chemical_formula_weight         381.37

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'
N N 0.0061 0.0033 '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                   8.0001(3)
_cell_length_b                   8.8042(4)
_cell_length_c                   13.4144(7)
_cell_angle_alpha                102.2380(10)
_cell_angle_beta                 93.1040(10)
_cell_angle_gamma                108.7080(10)
_cell_volume                     866.93(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8949
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      24.97

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_F_000             396
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.232
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_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  ccd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19573
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.518
_diffrn_reflns_theta_max         25.032
_diffrn_reflns_theta_full        25.032
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             3021
_reflns_number_gt                2384
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0935P)²+0.1340P] 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         3021
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1437
_refine_ls_wR_factor_gt          0.1266
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5302(3) 0.7651(3) 0.53198(18) 0.0358(6) Uani 1 1 d . . . . .
C2 C 0.5287(4) 0.7960(3) 0.43543(19) 0.0452(6) Uani 1 1 d . . . . .
C3 C 0.3785(4) 0.8016(4) 0.3864(2) 0.0568(8) Uani 1 1 d . . . . .
H3 H 0.3776 0.8214 0.3210 0.068 Uiso 1 1 calc R U . . .
C4 C 0.2266(4) 0.7775(3) 0.4348(2) 0.0531(7) Uani 1 1 d . . . . .
H4 H 0.1239 0.7816 0.4012 0.064 Uiso 1 1 calc R U . . .
C5 C 0.2246(3) 0.7476(3) 0.5318(2) 0.0426(6) Uani 1 1 d . . . . .
H5 H 0.1222 0.7324 0.5637 0.051 Uiso 1 1 calc R U . . .
C6 C 0.3783(3) 0.7406(3) 0.58061(17) 0.0335(5) Uani 1 1 d . . . . .
C7 C 0.4049(3) 0.7118(3) 0.68646(17) 0.0287(5) Uani 1 1 d . . . . .
C8 C 0.2650(3) 0.5591(3) 0.70545(17) 0.0322(5) Uani 1 1 d . . . . .
H8A H 0.1525 0.5780 0.7112 0.039 Uiso 1 1 calc R U . . .
H8B H 0.2469 0.4647 0.6483 0.039 Uiso 1 1 calc R U . . .
C9 C 0.3284(3) 0.5255(3) 0.80319(17) 0.0341(5) Uani 1 1 d . . . . .
C10 C 0.5007(3) 0.5691(3) 0.83595(18) 0.0383(6) Uani 1 1 d . . . . .
H10 H 0.5331 0.5492 0.8983 0.046 Uiso 1 1 calc R U . . .
C11 C 0.6413(3) 0.6462(3) 0.77990(18) 0.0356(6) Uani 1 1 d . . . . .
C12 C 0.8103(3) 0.6668(4) 0.8068(2) 0.0516(7) Uani 1 1 d . . . . .
H12A H 0.8963 0.7111 0.7671 0.062 Uiso 1 1 calc R U . . .
H12B H 0.8429 0.6370 0.8654 0.062 Uiso 1 1 calc R U . . .
C13 C 0.1999(3) 0.4384(3) 0.86560(19) 0.0384(6) Uani 1 1 d . . . . .
C14 C -0.1007(4) 0.2857(4) 0.8699(3) 0.0689(9) Uani 1 1 d . . . . .
H14A H -0.0666 0.3243 0.9430 0.103 Uiso 1 1 calc R U . . .
H14B H -0.1135 0.1709 0.8490 0.103 Uiso 1 1 calc R U . . .
H14C H -0.2118 0.2995 0.8520 0.103 Uiso 1 1 calc R U . . .
C15 C 0.4155(3) 0.8704(3) 0.76573(17) 0.0332(5) Uani 1 1 d . . . . .
C16 C 0.2429(4) 1.0293(4) 0.8388(2) 0.0594(8) Uani 1 1 d . . . . .
H16A H 0.1367 1.0483 0.8144 0.071 Uiso 1 1 calc R U . . .
H16B H 0.3454 1.1231 0.8356 0.071 Uiso 1 1 calc R U . . .
C17 C 0.2368(5) 1.0144(5) 0.9464(3) 0.0859(11) Uani 1 1 d . . . . .
H17A H 0.1369 0.9199 0.9492 0.129 Uiso 1 1 calc R U . . .
H17B H 0.2248 1.1122 0.9883 0.129 Uiso 1 1 calc R U . . .
H17C H 0.3447 1.0013 0.9715 0.129 Uiso 1 1 calc R U . . .
F1 F 0.6790(2) 0.8200(2) 0.39045(12) 0.0669(5) Uani 1 1 d . . . . .
N1 N 0.5786(2) 0.6878(2) 0.69216(14) 0.0351(5) Uani 1 1 d . . . . .
O1 O 0.0354(2) 0.3802(2) 0.81803(14) 0.0536(5) Uani 1 1 d . . . . .
O2 O 0.2383(3) 0.4198(3) 0.94843(16) 0.0692(7) Uani 1 1 d . . . . .
O3 O 0.5499(2) 0.9725(2) 0.81019(15) 0.0541(5) Uani 1 1 d . . . . .
O4 O 0.2541(2) 0.8798(2) 0.77305(14) 0.0489(5) Uani 1 1 d . . . . .
O5 O 0.7744(2) 0.6296(2) 0.55927(15) 0.0547(5) Uani 1 1 d . . . . .
O6 O 0.8367(2) 0.9152(2) 0.64977(14) 0.0512(5) Uani 1 1 d . . . . .
S1 S 0.70836(7) 0.75531(7) 0.60801(4) 0.0366(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.379(3) . ?
C1 C6 1.388(3) . ?
C1 S1 1.743(2) . ?
C2 F1 1.350(3) . ?
C2 C3 1.358(4) . ?
C3 C4 1.386(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.510(3) . ?
C7 N1 1.471(3) . ?
C7 C8 1.528(3) . ?
C7 C15 1.540(3) . ?
C8 C9 1.501(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.328(3) . ?
C9 C13 1.485(3) . ?
C10 C11 1.453(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.324(3) . ?
C11 N1 1.417(3) . ?
C12 H12A 0.9300 . ?
C12 H12B 0.9300 . ?
C13 O2 1.195(3) . ?
C13 O1 1.319(3) . ?
C14 O1 1.452(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 O3 1.184(3) . ?
C15 O4 1.328(3) . ?
C16 O4 1.453(3) . ?
C16 C17 1.479(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
N1 S1 1.6494(19) . ?
O5 S1 1.4269(18) . ?
O6 S1 1.4229(18) . ?

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
C2 C1 C6 120.3(2) . . ?
C2 C1 S1 127.6(2) . . ?
C6 C1 S1 112.05(17) . . ?
F1 C2 C3 120.7(2) . . ?
F1 C2 C1 118.8(2) . . ?
C3 C2 C1 120.5(2) . . ?
C2 C3 C4 119.4(2) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 121.4(3) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 118.7(2) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C5 C6 C1 119.7(2) . . ?
C5 C6 C7 127.1(2) . . ?
C1 C6 C7 113.15(19) . . ?
N1 C7 C6 104.21(17) . . ?
N1 C7 C8 108.43(17) . . ?
C6 C7 C8 114.76(18) . . ?
N1 C7 C15 109.79(17) . . ?
C6 C7 C15 107.59(17) . . ?
C8 C7 C15 111.75(18) . . ?
C9 C8 C7 108.77(18) . . ?
C9 C8 H8A 109.9 . . ?
C7 C8 H8A 109.9 . . ?
C9 C8 H8B 109.9 . . ?
C7 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
C10 C9 C13 117.6(2) . . ?
C10 C9 C8 121.5(2) . . ?
C13 C9 C8 120.93(19) . . ?
C9 C10 C11 123.7(2) . . ?
C9 C10 H10 118.2 . . ?
C11 C10 H10 118.2 . . ?
C12 C11 N1 124.2(2) . . ?
C12 C11 C10 122.1(2) . . ?
N1 C11 C10 113.62(19) . . ?
C11 C12 H12A 120.0 . . ?
C11 C12 H12B 120.0 . . ?
H12A C12 H12B 120.0 . . ?
O2 C13 O1 123.1(2) . . ?
O2 C13 C9 125.0(2) . . ?
O1 C13 C9 111.9(2) . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C15 O4 125.1(2) . . ?
O3 C15 C7 124.4(2) . . ?
O4 C15 C7 110.38(19) . . ?
O4 C16 C17 110.5(3) . . ?
O4 C16 H16A 109.6 . . ?
C17 C16 H16A 109.6 . . ?
O4 C16 H16B 109.6 . . ?
C17 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C11 N1 C7 119.60(18) . . ?
C11 N1 S1 122.91(15) . . ?
C7 N1 S1 115.82(15) . . ?
C13 O1 C14 116.7(2) . . ?
C15 O4 C16 117.1(2) . . ?
O6 S1 O5 116.59(12) . . ?
O6 S1 N1 112.62(11) . . ?
O5 S1 N1 109.44(11) . . ?
O6 S1 C1 111.37(11) . . ?
O5 S1 C1 112.47(12) . . ?
N1 S1 C1 91.69(10) . . ?

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 F1 179.7(2) . . . . ?
S1 C1 C2 F1 1.0(4) . . . . ?
C6 C1 C2 C3 -0.5(4) . . . . ?
S1 C1 C2 C3 -179.2(2) . . . . ?
F1 C2 C3 C4 -179.6(2) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
C3 C4 C5 C6 -0.5(4) . . . . ?
C4 C5 C6 C1 0.6(4) . . . . ?
C4 C5 C6 C7 179.2(2) . . . . ?
C2 C1 C6 C5 -0.1(4) . . . . ?
S1 C1 C6 C5 178.76(18) . . . . ?
C2 C1 C6 C7 -178.9(2) . . . . ?
S1 C1 C6 C7 0.0(3) . . . . ?
C5 C6 C7 N1 170.5(2) . . . . ?
C1 C6 C7 N1 -10.8(2) . . . . ?
C5 C6 C7 C8 52.1(3) . . . . ?
C1 C6 C7 C8 -129.2(2) . . . . ?
C5 C6 C7 C15 -72.9(3) . . . . ?
C1 C6 C7 C15 105.7(2) . . . . ?
N1 C7 C8 C9 52.0(2) . . . . ?
C6 C7 C8 C9 168.02(18) . . . . ?
C15 C7 C8 C9 -69.1(2) . . . . ?
C7 C8 C9 C10 -28.2(3) . . . . ?
C7 C8 C9 C13 153.2(2) . . . . ?
C13 C9 C10 C11 176.3(2) . . . . ?
C8 C9 C10 C11 -2.3(4) . . . . ?
C9 C10 C11 C12 -170.2(3) . . . . ?
C9 C10 C11 N1 6.6(3) . . . . ?
C10 C9 C13 O2 8.4(4) . . . . ?
C8 C9 C13 O2 -173.0(2) . . . . ?
C10 C9 C13 O1 -170.7(2) . . . . ?
C8 C9 C13 O1 8.0(3) . . . . ?
N1 C7 C15 O3 13.0(3) . . . . ?
C6 C7 C15 O3 -99.8(3) . . . . ?
C8 C7 C15 O3 133.3(2) . . . . ?
N1 C7 C15 O4 -170.08(18) . . . . ?
C6 C7 C15 O4 77.1(2) . . . . ?
C8 C7 C15 O4 -49.7(2) . . . . ?
C12 C11 N1 C7 -160.2(2) . . . . ?
C10 C11 N1 C7 23.0(3) . . . . ?
C12 C11 N1 S1 4.5(4) . . . . ?
C10 C11 N1 S1 -172.29(17) . . . . ?
C6 C7 N1 C11 -175.77(19) . . . . ?
C8 C7 N1 C11 -53.1(3) . . . . ?
C15 C7 N1 C11 69.2(2) . . . . ?
C6 C7 N1 S1 18.5(2) . . . . ?
C8 C7 N1 S1 141.17(16) . . . . ?
C15 C7 N1 S1 -96.49(19) . . . . ?
O2 C13 O1 C14 -1.9(4) . . . . ?
C9 C13 O1 C14 177.2(2) . . . . ?
O3 C15 O4 C16 1.7(4) . . . . ?
C7 C15 O4 C16 -175.2(2) . . . . ?
C17 C16 O4 C15 -86.7(3) . . . . ?
C11 N1 S1 O6 -68.0(2) . . . . ?
C7 N1 S1 O6 97.25(17) . . . . ?
C11 N1 S1 O5 63.4(2) . . . . ?
C7 N1 S1 O5 -131.36(17) . . . . ?
C11 N1 S1 C1 178.00(19) . . . . ?
C7 N1 S1 C1 -16.78(17) . . . . ?
C2 C1 S1 O6 73.0(2) . . . . ?
C6 C1 S1 O6 -105.80(19) . . . . ?
C2 C1 S1 O5 -60.0(2) . . . . ?
C6 C1 S1 O5 121.21(18) . . . . ?
C2 C1 S1 N1 -171.9(2) . . . . ?
C6 C1 S1 N1 9.34(19) . . . . ?

_refine_diff_density_max         0.237
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.049



