# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_181206b
_database_code_depnum_ccdc_archive 'CCDC 2070093'
loop_
_audit_author_name
_audit_author_address
SANYUANHAUNYI
;WHUT
China
;
_audit_update_record             
;
2021-03-13 deposited with the CCDC.	2021-06-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 F N O2 S'
_chemical_formula_weight         301.33

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.4301(5)
_cell_length_b                   7.7504(6)
_cell_length_c                   14.9740(12)
_cell_angle_alpha                95.348(2)
_cell_angle_beta                 100.866(3)
_cell_angle_gamma                105.796(3)
_cell_volume                     696.89(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    861
_cell_measurement_theta_min      2.764
_cell_measurement_theta_max      22.945

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8971
_exptl_absorpt_correction_T_max  0.9569
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3439
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_sigmaI/netI    0.1046
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2396
_reflns_number_gt                1515
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1464P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2396
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1269
_refine_ls_R_factor_gt           0.0836
_refine_ls_wR_factor_ref         0.2441
_refine_ls_wR_factor_gt          0.2110
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.4880(5) 0.3883(5) 0.1216(2) 0.0681(10) Uani 1 1 d . . .
N1 N 0.1313(9) -0.0709(8) 0.1255(3) 0.0759(16) Uani 1 1 d . . .
O1 O -0.2395(6) 0.4635(5) 0.0232(3) 0.0694(13) Uani 1 1 d . . .
O2 O -0.5384(6) 0.1829(5) -0.0119(2) 0.0584(11) Uani 1 1 d . . .
S1 S -0.37075(19) 0.31752(17) 0.05288(9) 0.0459(5) Uani 1 1 d . . .
C1 C 0.0743(8) 0.0539(8) 0.1164(3) 0.0490(13) Uani 1 1 d . . .
C2 C 0.0094(7) 0.2146(7) 0.1038(3) 0.0415(12) Uani 1 1 d . . .
H2 H 0.0473 0.2725 0.0511 0.050 Uiso 1 1 calc R . .
C3 C -0.2075(7) 0.2199(6) 0.1261(3) 0.0368(11) Uani 1 1 d . . .
H3 H -0.2866 0.1153 0.1512 0.044 Uiso 1 1 calc R . .
C4 C 0.0029(7) 0.3389(6) 0.1862(3) 0.0392(12) Uani 1 1 d . . .
H4 H 0.0358 0.4673 0.1789 0.047 Uiso 1 1 calc R . .
C5 C 0.0749(7) 0.3058(6) 0.2823(3) 0.0384(11) Uani 1 1 d . . .
C6 C -0.0752(8) 0.2516(7) 0.3366(4) 0.0483(13) Uani 1 1 d . . .
H6 H -0.2258 0.2293 0.3121 0.058 Uiso 1 1 calc R . .
C7 C -0.0049(8) 0.2298(7) 0.4270(4) 0.0479(13) Uani 1 1 d . . .
H7 H -0.1092 0.1953 0.4624 0.057 Uiso 1 1 calc R . .
C8 C 0.2168(7) 0.2579(6) 0.4658(3) 0.0391(11) Uani 1 1 d . . .
C9 C 0.3654(8) 0.3122(7) 0.4092(3) 0.0465(13) Uani 1 1 d . . .
H9 H 0.5162 0.3334 0.4328 0.056 Uiso 1 1 calc R . .
C10 C 0.2957(7) 0.3347(7) 0.3210(3) 0.0447(12) Uani 1 1 d . . .
H10 H 0.3998 0.3706 0.2856 0.054 Uiso 1 1 calc R . .
C11 C 0.2924(8) 0.2382(6) 0.5628(3) 0.0395(11) Uani 1 1 d . . .
C12 C 0.1815(9) 0.2735(7) 0.6304(4) 0.0519(14) Uani 1 1 d . . .
H12 H 0.0541 0.3089 0.6139 0.062 Uiso 1 1 calc R . .
C13 C 0.2544(10) 0.2577(8) 0.7209(4) 0.0590(16) Uani 1 1 d . . .
H13 H 0.1764 0.2815 0.7646 0.071 Uiso 1 1 calc R . .
C14 C 0.4416(10) 0.2070(8) 0.7462(4) 0.0606(16) Uani 1 1 d . . .
H14 H 0.4917 0.1967 0.8073 0.073 Uiso 1 1 calc R . .
C15 C 0.5563(9) 0.1711(8) 0.6817(4) 0.0576(15) Uani 1 1 d . . .
H15 H 0.6842 0.1371 0.6993 0.069 Uiso 1 1 calc R . .
C16 C 0.4830(8) 0.1853(7) 0.5911(4) 0.0490(13) Uani 1 1 d . . .
H16 H 0.5611 0.1593 0.5479 0.059 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0610(19) 0.084(2) 0.069(2) 0.0030(17) 0.0107(17) 0.0425(18)
N1 0.098(4) 0.092(4) 0.061(3) 0.015(3) 0.012(3) 0.068(4)
O1 0.047(2) 0.067(3) 0.105(3) 0.053(2) 0.018(2) 0.0210(19)
O2 0.052(2) 0.054(2) 0.056(2) -0.0022(18) -0.0128(18) 0.0152(18)
S1 0.0371(7) 0.0480(8) 0.0575(9) 0.0201(6) 0.0075(6) 0.0188(6)
C1 0.046(3) 0.069(4) 0.036(3) 0.010(3) 0.004(2) 0.027(3)
C2 0.036(2) 0.050(3) 0.041(3) 0.011(2) 0.007(2) 0.017(2)
C3 0.032(2) 0.035(3) 0.045(3) 0.016(2) 0.008(2) 0.010(2)
C4 0.036(2) 0.035(3) 0.044(3) 0.010(2) 0.008(2) 0.006(2)
C5 0.035(2) 0.035(3) 0.041(3) 0.003(2) 0.005(2) 0.007(2)
C6 0.028(2) 0.059(3) 0.053(3) 0.008(3) 0.003(2) 0.008(2)
C7 0.036(3) 0.062(3) 0.048(3) 0.010(3) 0.015(2) 0.013(2)
C8 0.039(3) 0.040(3) 0.034(3) -0.004(2) 0.005(2) 0.009(2)
C9 0.033(2) 0.057(3) 0.043(3) 0.008(2) 0.003(2) 0.007(2)
C10 0.036(3) 0.058(3) 0.040(3) 0.011(2) 0.010(2) 0.012(2)
C11 0.042(3) 0.032(3) 0.041(3) 0.004(2) 0.011(2) 0.005(2)
C12 0.051(3) 0.057(3) 0.045(3) 0.006(3) 0.013(3) 0.010(3)
C13 0.070(4) 0.056(4) 0.045(3) 0.002(3) 0.023(3) 0.004(3)
C14 0.078(4) 0.062(4) 0.036(3) 0.015(3) 0.009(3) 0.012(3)
C15 0.057(3) 0.056(4) 0.055(4) 0.015(3) 0.005(3) 0.013(3)
C16 0.046(3) 0.053(3) 0.047(3) 0.008(2) 0.009(2) 0.014(2)

_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
F1 S1 1.529(3) . ?
N1 C1 1.135(7) . ?
O1 S1 1.380(4) . ?
O2 S1 1.413(4) . ?
S1 C3 1.741(4) . ?
C1 C2 1.435(7) . ?
C2 C3 1.504(6) . ?
C2 C4 1.508(7) . ?
C2 H2 0.9800 . ?
C3 C4 1.483(6) . ?
C3 H3 0.9800 . ?
C4 C5 1.494(6) . ?
C4 H4 0.9800 . ?
C5 C10 1.376(6) . ?
C5 C6 1.381(6) . ?
C6 C7 1.385(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.383(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.401(7) . ?
C8 C11 1.479(7) . ?
C9 C10 1.356(7) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.391(7) . ?
C11 C16 1.399(7) . ?
C12 C13 1.376(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.364(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.373(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.375(7) . ?
C15 H15 0.9300 . ?
C16 H16 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
O1 S1 O2 119.6(3) . . ?
O1 S1 F1 108.8(3) . . ?
O2 S1 F1 105.8(2) . . ?
O1 S1 C3 110.5(2) . . ?
O2 S1 C3 110.9(2) . . ?
F1 S1 C3 99.1(2) . . ?
N1 C1 C2 177.9(6) . . ?
C1 C2 C3 117.1(4) . . ?
C1 C2 C4 119.8(4) . . ?
C3 C2 C4 59.0(3) . . ?
C1 C2 H2 116.2 . . ?
C3 C2 H2 116.2 . . ?
C4 C2 H2 116.2 . . ?
C4 C3 C2 60.7(3) . . ?
C4 C3 S1 118.6(3) . . ?
C2 C3 S1 116.9(3) . . ?
C4 C3 H3 116.4 . . ?
C2 C3 H3 116.4 . . ?
S1 C3 H3 116.4 . . ?
C3 C4 C5 120.2(4) . . ?
C3 C4 C2 60.4(3) . . ?
C5 C4 C2 121.9(4) . . ?
C3 C4 H4 114.6 . . ?
C5 C4 H4 114.6 . . ?
C2 C4 H4 114.6 . . ?
C10 C5 C6 117.5(4) . . ?
C10 C5 C4 120.8(4) . . ?
C6 C5 C4 121.7(4) . . ?
C5 C6 C7 121.0(4) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C8 C7 C6 121.6(4) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C9 116.3(4) . . ?
C7 C8 C11 121.6(4) . . ?
C9 C8 C11 122.1(4) . . ?
C10 C9 C8 121.9(4) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C9 C10 C5 121.7(5) . . ?
C9 C10 H10 119.1 . . ?
C5 C10 H10 119.1 . . ?
C12 C11 C16 116.8(5) . . ?
C12 C11 C8 122.2(5) . . ?
C16 C11 C8 121.0(4) . . ?
C13 C12 C11 122.0(5) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C14 C13 C12 119.7(5) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 120.2(5) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C16 120.3(5) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 121.0(5) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?

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
N1 C1 C2 C3 179(100) . . . . ?
N1 C1 C2 C4 -113(17) . . . . ?
C1 C2 C3 C4 110.1(5) . . . . ?
C1 C2 C3 S1 -140.6(4) . . . . ?
C4 C2 C3 S1 109.3(4) . . . . ?
O1 S1 C3 C4 32.9(5) . . . . ?
O2 S1 C3 C4 167.9(3) . . . . ?
F1 S1 C3 C4 -81.2(4) . . . . ?
O1 S1 C3 C2 -36.6(5) . . . . ?
O2 S1 C3 C2 98.4(4) . . . . ?
F1 S1 C3 C2 -150.7(4) . . . . ?
C2 C3 C4 C5 -111.8(5) . . . . ?
S1 C3 C4 C5 141.6(4) . . . . ?
S1 C3 C4 C2 -106.5(4) . . . . ?
C1 C2 C4 C3 -105.6(5) . . . . ?
C1 C2 C4 C5 3.6(7) . . . . ?
C3 C2 C4 C5 109.2(5) . . . . ?
C3 C4 C5 C10 144.1(5) . . . . ?
C2 C4 C5 C10 72.2(6) . . . . ?
C3 C4 C5 C6 -38.2(7) . . . . ?
C2 C4 C5 C6 -110.1(6) . . . . ?
C10 C5 C6 C7 0.9(8) . . . . ?
C4 C5 C6 C7 -176.9(5) . . . . ?
C5 C6 C7 C8 -1.2(8) . . . . ?
C6 C7 C8 C9 0.9(8) . . . . ?
C6 C7 C8 C11 178.8(5) . . . . ?
C7 C8 C9 C10 -0.4(8) . . . . ?
C11 C8 C9 C10 -178.2(5) . . . . ?
C8 C9 C10 C5 0.2(8) . . . . ?
C6 C5 C10 C9 -0.4(8) . . . . ?
C4 C5 C10 C9 177.4(5) . . . . ?
C7 C8 C11 C12 -30.3(7) . . . . ?
C9 C8 C11 C12 147.4(5) . . . . ?
C7 C8 C11 C16 150.7(5) . . . . ?
C9 C8 C11 C16 -31.6(7) . . . . ?
C16 C11 C12 C13 0.1(7) . . . . ?
C8 C11 C12 C13 -179.0(5) . . . . ?
C11 C12 C13 C14 0.4(8) . . . . ?
C12 C13 C14 C15 -0.3(9) . . . . ?
C13 C14 C15 C16 -0.3(9) . . . . ?
C14 C15 C16 C11 0.7(8) . . . . ?
C12 C11 C16 C15 -0.6(7) . . . . ?
C8 C11 C16 C15 178.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.914
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.120
####################################################################### 
# 
# 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_210114f
_database_code_depnum_ccdc_archive 'CCDC 2070095'
loop_
_audit_author_name
_audit_author_address
SANYUANHAUNER
;WHUT
China
;
_audit_update_record             
;
2021-03-13 deposited with the CCDC.	2021-06-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 F N O2 S'
_chemical_formula_weight         225.23

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   7.7520(6)
_cell_length_b                   23.8360(19)
_cell_length_c                   5.6189(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.925(2)
_cell_angle_gamma                90.00
_cell_volume                     1028.33(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1952
_cell_measurement_theta_min      2.564
_cell_measurement_theta_max      27.531

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.307
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9003
_exptl_absorpt_correction_T_max  0.9671
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4917
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_sigmaI/netI    0.0587
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.79
_diffrn_reflns_theta_max         25.02
_reflns_number_total             1818
_reflns_number_gt                1409
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0288P)²+2.4729P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1818
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0776
_refine_ls_wR_factor_ref         0.1669
_refine_ls_wR_factor_gt          0.1600
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_restrained_S_all      1.146
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 1.3985(4) 0.42412(17) 0.5191(6) 0.0805(11) Uani 1 1 d . . .
N1 N 1.1615(7) 0.3000(2) 0.1642(9) 0.0720(15) Uani 1 1 d . . .
O1 O 1.2092(6) 0.49639(16) 0.5933(7) 0.0750(13) Uani 1 1 d . . .
O2 O 1.1533(5) 0.43867(15) 0.2387(6) 0.0564(10) Uani 1 1 d . . .
S1 S 1.21036(16) 0.44441(5) 0.4835(2) 0.0445(4) Uani 1 1 d . . .
C1 C 1.1306(7) 0.31729(19) 0.3382(9) 0.0451(12) Uani 1 1 d . . .
C2 C 1.0849(6) 0.33650(19) 0.5654(8) 0.0415(11) Uani 1 1 d . . .
H2 H 1.0940 0.3080 0.6922 0.050 Uiso 1 1 calc R . .
C3 C 1.1166(6) 0.39539(19) 0.6525(8) 0.0373(10) Uani 1 1 d . . .
H3 H 1.1443 0.3997 0.8271 0.045 Uiso 1 1 calc R . .
C4 C 0.9368(6) 0.37648(18) 0.5655(8) 0.0359(10) Uani 1 1 d . . .
H4 H 0.8898 0.3907 0.4061 0.043 Uiso 1 1 calc R . .
C5 C 0.8044(6) 0.36852(19) 0.7295(8) 0.0374(11) Uani 1 1 d . . .
C6 C 0.7690(6) 0.4093(2) 0.8871(8) 0.0450(12) Uani 1 1 d . . .
H6 H 0.8328 0.4425 0.8983 0.054 Uiso 1 1 calc R . .
C7 C 0.6403(7) 0.4017(3) 1.0286(9) 0.0605(16) Uani 1 1 d . . .
H7 H 0.6170 0.4297 1.1348 0.073 Uiso 1 1 calc R . .
C8 C 0.5467(7) 0.3534(3) 1.0144(11) 0.0643(17) Uani 1 1 d . . .
H8 H 0.4596 0.3483 1.1109 0.077 Uiso 1 1 calc R . .
C9 C 0.5805(7) 0.3128(3) 0.8593(12) 0.0681(17) Uani 1 1 d . . .
H9 H 0.5159 0.2798 0.8482 0.082 Uiso 1 1 calc R . .
C10 C 0.7104(7) 0.3201(2) 0.7177(11) 0.0586(15) Uani 1 1 d . . .
H10 H 0.7341 0.2917 0.6132 0.070 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0468(19) 0.108(3) 0.089(3) 0.029(2) 0.0152(17) 0.0089(18)
N1 0.109(4) 0.046(3) 0.070(3) -0.013(3) 0.045(3) -0.014(3)
O1 0.105(3) 0.044(2) 0.078(3) -0.016(2) 0.021(2) -0.021(2)
O2 0.073(2) 0.060(2) 0.0368(19) 0.0095(17) 0.0088(17) -0.0104(19)
S1 0.0477(7) 0.0412(7) 0.0452(7) 0.0005(6) 0.0093(5) -0.0067(6)
C1 0.063(3) 0.033(3) 0.044(3) -0.003(2) 0.024(2) -0.001(2)
C2 0.056(3) 0.031(2) 0.040(3) 0.003(2) 0.018(2) 0.000(2)
C3 0.042(3) 0.042(3) 0.029(2) -0.0014(19) 0.0067(19) -0.001(2)
C4 0.042(3) 0.036(2) 0.030(2) -0.0002(19) 0.0050(19) -0.004(2)
C5 0.036(2) 0.041(3) 0.034(2) 0.002(2) 0.0019(19) -0.002(2)
C6 0.038(3) 0.058(3) 0.039(3) -0.004(2) 0.003(2) -0.007(2)
C7 0.047(3) 0.092(5) 0.042(3) -0.010(3) 0.006(2) 0.002(3)
C8 0.039(3) 0.095(5) 0.062(4) 0.015(3) 0.018(3) 0.004(3)
C9 0.057(4) 0.056(4) 0.095(5) 0.016(3) 0.021(3) -0.018(3)
C10 0.059(3) 0.041(3) 0.080(4) -0.003(3) 0.024(3) -0.007(3)

_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
F1 S1 1.523(3) . ?
N1 C1 1.118(6) . ?
O1 S1 1.385(4) . ?
O2 S1 1.392(3) . ?
S1 C3 1.728(4) . ?
C1 C2 1.445(6) . ?
C2 C4 1.492(6) . ?
C2 C3 1.496(6) . ?
C2 H2 0.9800 . ?
C3 C4 1.482(6) . ?
C3 H3 0.9800 . ?
C4 C5 1.483(6) . ?
C4 H4 0.9800 . ?
C5 C10 1.362(7) . ?
C5 C6 1.368(6) . ?
C6 C7 1.371(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.356(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.353(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.378(7) . ?
C9 H9 0.9300 . ?
C10 H10 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
O1 S1 O2 120.5(3) . . ?
O1 S1 F1 106.9(3) . . ?
O2 S1 F1 105.5(2) . . ?
O1 S1 C3 109.3(2) . . ?
O2 S1 C3 112.1(2) . . ?
F1 S1 C3 100.4(2) . . ?
N1 C1 C2 176.4(5) . . ?
C1 C2 C4 119.0(4) . . ?
C1 C2 C3 122.5(4) . . ?
C4 C2 C3 59.5(3) . . ?
C1 C2 H2 114.9 . . ?
C4 C2 H2 114.9 . . ?
C3 C2 H2 114.9 . . ?
C4 C3 C2 60.2(3) . . ?
C4 C3 S1 118.2(3) . . ?
C2 C3 S1 121.1(3) . . ?
C4 C3 H3 115.4 . . ?
C2 C3 H3 115.4 . . ?
S1 C3 H3 115.4 . . ?
C3 C4 C5 122.3(4) . . ?
C3 C4 C2 60.4(3) . . ?
C5 C4 C2 121.1(4) . . ?
C3 C4 H4 114.2 . . ?
C5 C4 H4 114.2 . . ?
C2 C4 H4 114.2 . . ?
C10 C5 C6 118.7(5) . . ?
C10 C5 C4 119.3(4) . . ?
C6 C5 C4 121.9(4) . . ?
C5 C6 C7 120.5(5) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 120.3(5) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C9 C8 C7 119.7(5) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 120.2(5) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C5 C10 C9 120.5(5) . . ?
C5 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?

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
N1 C1 C2 C4 -101(10) . . . . ?
N1 C1 C2 C3 -171(10) . . . . ?
C1 C2 C3 C4 107.0(5) . . . . ?
C1 C2 C3 S1 0.2(7) . . . . ?
C4 C2 C3 S1 -106.8(4) . . . . ?
O1 S1 C3 C4 103.9(4) . . . . ?
O2 S1 C3 C4 -32.4(4) . . . . ?
F1 S1 C3 C4 -144.0(3) . . . . ?
O1 S1 C3 C2 174.2(4) . . . . ?
O2 S1 C3 C2 37.9(4) . . . . ?
F1 S1 C3 C2 -73.6(4) . . . . ?
C2 C3 C4 C5 110.2(5) . . . . ?
S1 C3 C4 C5 -138.2(4) . . . . ?
S1 C3 C4 C2 111.6(4) . . . . ?
C1 C2 C4 C3 -112.7(5) . . . . ?
C1 C2 C4 C5 135.3(4) . . . . ?
C3 C2 C4 C5 -112.0(5) . . . . ?
C3 C4 C5 C10 -131.1(5) . . . . ?
C2 C4 C5 C10 -58.7(6) . . . . ?
C3 C4 C5 C6 51.3(6) . . . . ?
C2 C4 C5 C6 123.7(5) . . . . ?
C10 C5 C6 C7 -0.6(7) . . . . ?
C4 C5 C6 C7 177.0(5) . . . . ?
C5 C6 C7 C8 0.2(8) . . . . ?
C6 C7 C8 C9 -0.2(9) . . . . ?
C7 C8 C9 C10 0.5(9) . . . . ?
C6 C5 C10 C9 1.0(8) . . . . ?
C4 C5 C10 C9 -176.7(5) . . . . ?
C8 C9 C10 C5 -0.9(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.065
