# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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_s2491
_audit_block_doi                 10.5517/ccdc.csd.cc1k7t2p
_database_code_depnum_ccdc_archive 'CCDC 1437472'
loop_
_audit_author_name
_audit_author_address
'Ulrich Floerke'
;University of Paderborn
Germany
;
_audit_update_record             
;
2018-12-13 deposited with the CCDC.	2020-02-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H11 N O2 S'
_chemical_formula_sum            'C10 H11 N O2 S'
_chemical_formula_weight         209.26

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'
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                   11.7767(16)
_cell_length_b                   9.1218(13)
_cell_length_c                   9.7623(14)
_cell_angle_alpha                90
_cell_angle_beta                 106.287(3)
_cell_angle_gamma                90
_cell_volume                     1006.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    541
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      22.06

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.293
_shelx_estimated_absorpt_T_min   0.879
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_absorpt_correction_T_min  0.8793
_exptl_absorpt_correction_T_max  0.9491

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS SMART APEX'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            9276
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.801
_diffrn_reflns_theta_max         27.872
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2400
_reflns_number_gt                2144
_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       'SMART (Bruker, 2002)'
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and local programs'

_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)+(0.0557P)²+0.3479P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2400
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0982
_refine_ls_wR_factor_gt          0.0945
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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 0.92049(3) -0.00650(4) 0.81555(4) 0.03250(13) Uani 1 1 d . . . . .
O1 O 0.74175(10) 0.19683(11) 0.38194(10) 0.0342(3) Uani 1 1 d . . . . .
O2 O 0.85823(9) -0.01970(10) 0.53309(10) 0.0278(2) Uani 1 1 d . . . . .
N1 N 0.79466(10) 0.17963(11) 0.62631(11) 0.0222(2) Uani 1 1 d . . . . .
H1A H 0.7836 0.2229 0.7021 0.027 Uiso 1 1 calc R U . . .
C1 C 0.74716(11) 0.25192(13) 0.49727(13) 0.0222(3) Uani 1 1 d . . . . .
C2 C 0.70180(11) 0.40245(13) 0.50863(13) 0.0207(2) Uani 1 1 d . . . . .
C3 C 0.74247(11) 0.49208(13) 0.62781(13) 0.0213(3) Uani 1 1 d . . . . .
H3A H 0.7992 0.4560 0.7104 0.026 Uiso 1 1 calc R U . . .
C4 C 0.69984(11) 0.63459(13) 0.62572(14) 0.0238(3) Uani 1 1 d . . . . .
H4A H 0.7275 0.6950 0.7076 0.029 Uiso 1 1 calc R U . . .
C5 C 0.61741(11) 0.69001(14) 0.50584(14) 0.0234(3) Uani 1 1 d . . . . .
C6 C 0.57525(12) 0.59844(15) 0.38770(14) 0.0271(3) Uani 1 1 d . . . . .
H6A H 0.5171 0.6337 0.3060 0.033 Uiso 1 1 calc R U . . .
C7 C 0.61738(12) 0.45710(14) 0.38885(13) 0.0258(3) Uani 1 1 d . . . . .
H7A H 0.5887 0.3964 0.3074 0.031 Uiso 1 1 calc R U . . .
C8 C 0.57475(13) 0.84596(14) 0.50207(16) 0.0305(3) Uani 1 1 d . . . . .
H8A H 0.6121 0.8933 0.5938 0.046 Uiso 1 1 calc R U . . .
H8B H 0.4886 0.8468 0.4845 0.046 Uiso 1 1 calc R U . . .
H8C H 0.5958 0.8993 0.4255 0.046 Uiso 1 1 calc R U . . .
C9 C 0.85703(11) 0.04866(13) 0.65177(14) 0.0226(3) Uani 1 1 d . . . . .
C10 C 0.92655(13) -0.15457(14) 0.54558(17) 0.0334(3) Uani 1 1 d . . . . .
H10A H 1.0092 -0.1348 0.5975 0.050 Uiso 1 1 calc R U . . .
H10B H 0.9223 -0.1917 0.4501 0.050 Uiso 1 1 calc R U . . .
H10C H 0.8941 -0.2279 0.5976 0.050 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 C9 1.6425(13) . ?
O1 C1 1.2182(15) . ?
O2 C9 1.3193(16) . ?
O2 C10 1.4563(15) . ?
N1 C9 1.3879(16) . ?
N1 C1 1.3926(15) . ?
N1 H1A 0.8800 . ?
C1 C2 1.4887(17) . ?
C2 C3 1.3925(17) . ?
C2 C7 1.3972(17) . ?
C3 C4 1.3916(17) . ?
C3 H3A 0.9500 . ?
C4 C5 1.3894(18) . ?
C4 H4A 0.9500 . ?
C5 C6 1.3976(19) . ?
C5 C8 1.5056(17) . ?
C6 C7 1.3804(18) . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

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
C9 O2 C10 117.87(11) . . ?
C9 N1 C1 128.89(10) . . ?
C9 N1 H1A 115.6 . . ?
C1 N1 H1A 115.6 . . ?
O1 C1 N1 122.98(11) . . ?
O1 C1 C2 121.50(11) . . ?
N1 C1 C2 115.52(10) . . ?
C3 C2 C7 119.15(11) . . ?
C3 C2 C1 123.87(11) . . ?
C7 C2 C1 116.92(11) . . ?
C4 C3 C2 119.87(12) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C5 C4 C3 121.08(12) . . ?
C5 C4 H4A 119.5 . . ?
C3 C4 H4A 119.5 . . ?
C4 C5 C6 118.70(12) . . ?
C4 C5 C8 120.92(12) . . ?
C6 C5 C8 120.37(12) . . ?
C7 C6 C5 120.52(12) . . ?
C7 C6 H6A 119.7 . . ?
C5 C6 H6A 119.7 . . ?
C6 C7 C2 120.65(12) . . ?
C6 C7 H7A 119.7 . . ?
C2 C7 H7A 119.7 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 N1 112.64(11) . . ?
O2 C9 S1 126.59(10) . . ?
N1 C9 S1 120.77(9) . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

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
C9 N1 C1 O1 9.8(2) . . . . ?
C9 N1 C1 C2 -170.64(11) . . . . ?
O1 C1 C2 C3 -154.66(13) . . . . ?
N1 C1 C2 C3 25.79(17) . . . . ?
O1 C1 C2 C7 22.32(18) . . . . ?
N1 C1 C2 C7 -157.24(11) . . . . ?
C7 C2 C3 C4 -0.69(18) . . . . ?
C1 C2 C3 C4 176.22(11) . . . . ?
C2 C3 C4 C5 -0.42(19) . . . . ?
C3 C4 C5 C6 1.68(19) . . . . ?
C3 C4 C5 C8 -177.80(12) . . . . ?
C4 C5 C6 C7 -1.9(2) . . . . ?
C8 C5 C6 C7 177.63(12) . . . . ?
C5 C6 C7 C2 0.8(2) . . . . ?
C3 C2 C7 C6 0.51(19) . . . . ?
C1 C2 C7 C6 -176.61(12) . . . . ?
C10 O2 C9 N1 176.62(10) . . . . ?
C10 O2 C9 S1 -3.00(17) . . . . ?
C1 N1 C9 O2 -7.76(18) . . . . ?
C1 N1 C9 S1 171.88(10) . . . . ?

_refine_diff_density_max         0.362
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.049

_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_s2493
_audit_block_doi                 10.5517/ccdc.csd.cc1k7t1n
_database_code_depnum_ccdc_archive 'CCDC 1437471'
loop_
_audit_author_name
_audit_author_address
'Ulrich Floerke'
;University of Paderborn
Germany
;
_audit_update_record             
;
2018-12-13 deposited with the CCDC.	2020-02-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H8 F N O2 S'
_chemical_formula_sum            'C9 H8 F N O2 S'
_chemical_formula_weight         213.22

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      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                   11.7032(18)
_cell_length_b                   8.7287(13)
_cell_length_c                   9.8686(15)
_cell_angle_alpha                90
_cell_angle_beta                 111.415(3)
_cell_angle_gamma                90
_cell_volume                     938.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    3066
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      28.15

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_absorpt_coefficient_mu    0.331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_absorpt_correction_T_min  0.9015
_exptl_absorpt_correction_T_max  0.9520

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS SMART APEX'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            8674
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.869
_diffrn_reflns_theta_max         27.875
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2240
_reflns_number_gt                1976
_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       'SMART (Bruker, 2002)'
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and local programs'

_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)+(0.0491P)²+0.3239P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2240
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0902
_refine_ls_wR_factor_gt          0.0865
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
S1 S 0.92501(3) 1.01510(4) 0.80315(4) 0.02732(12) Uani 1 1 d . . . . .
O1 O 0.74224(10) 0.77845(11) 0.36656(10) 0.0269(2) Uani 1 1 d . . . . .
O2 O 0.85168(9) 1.01836(11) 0.51539(11) 0.0248(2) Uani 1 1 d . . . . .
N1 N 0.79440(10) 0.81169(12) 0.61181(12) 0.0196(2) Uani 1 1 d . . . . .
H1A H 0.7843 0.7702 0.6879 0.023 Uiso 1 1 calc R U . . .
F1 F 0.54038(9) 0.15662(10) 0.50698(11) 0.0413(3) Uani 1 1 d . . . . .
C1 C 0.74663(11) 0.72908(14) 0.48341(14) 0.0180(3) Uani 1 1 d . . . . .
C2 C 0.69722(11) 0.57422(14) 0.49693(13) 0.0177(3) Uani 1 1 d . . . . .
C3 C 0.61296(12) 0.51085(15) 0.36947(15) 0.0230(3) Uani 1 1 d . . . . .
H3A H 0.5924 0.5647 0.2801 0.028 Uiso 1 1 calc R U . . .
C4 C 0.55930(13) 0.37034(16) 0.37255(16) 0.0266(3) Uani 1 1 d . . . . .
H4A H 0.5003 0.3280 0.2868 0.032 Uiso 1 1 calc R U . . .
C5 C 0.59368(13) 0.29370(15) 0.50297(16) 0.0258(3) Uani 1 1 d . . . . .
C6 C 0.67906(13) 0.34961(15) 0.63008(15) 0.0242(3) Uani 1 1 d . . . . .
H6A H 0.7022 0.2922 0.7178 0.029 Uiso 1 1 calc R U . . .
C7 C 0.73037(12) 0.49230(14) 0.62659(15) 0.0193(3) Uani 1 1 d . . . . .
H7A H 0.7885 0.5342 0.7132 0.023 Uiso 1 1 calc R U . . .
C8 C 0.85576(12) 0.95031(15) 0.63665(14) 0.0196(3) Uani 1 1 d . . . . .
C9 C 0.91739(14) 1.16215(16) 0.52849(17) 0.0294(3) Uani 1 1 d . . . . .
H9A H 0.8779 1.2412 0.5669 0.044 Uiso 1 1 calc R U . . .
H9B H 0.9160 1.1935 0.4325 0.044 Uiso 1 1 calc R U . . .
H9C H 1.0026 1.1488 0.5949 0.044 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 C8 1.6444(14) . ?
O1 C1 1.2144(16) . ?
O2 C8 1.3211(16) . ?
O2 C9 1.4529(16) . ?
N1 C8 1.3825(16) . ?
N1 C1 1.3859(16) . ?
N1 H1A 0.8800 . ?
F1 C5 1.3566(16) . ?
C1 C2 1.4952(17) . ?
C2 C7 1.3916(18) . ?
C2 C3 1.3982(18) . ?
C3 C4 1.3833(19) . ?
C3 H3A 0.9500 . ?
C4 C5 1.374(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.377(2) . ?
C6 C7 1.3886(18) . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

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
C8 O2 C9 117.70(11) . . ?
C8 N1 C1 128.86(11) . . ?
C8 N1 H1A 115.6 . . ?
C1 N1 H1A 115.6 . . ?
O1 C1 N1 123.14(12) . . ?
O1 C1 C2 121.46(11) . . ?
N1 C1 C2 115.39(11) . . ?
C7 C2 C3 119.48(12) . . ?
C7 C2 C1 124.02(11) . . ?
C3 C2 C1 116.50(11) . . ?
C4 C3 C2 120.52(13) . . ?
C4 C3 H3A 119.7 . . ?
C2 C3 H3A 119.7 . . ?
C5 C4 C3 118.18(13) . . ?
C5 C4 H4A 120.9 . . ?
C3 C4 H4A 120.9 . . ?
F1 C5 C4 118.44(13) . . ?
F1 C5 C6 118.33(13) . . ?
C4 C5 C6 123.22(13) . . ?
C5 C6 C7 118.16(13) . . ?
C5 C6 H6A 120.9 . . ?
C7 C6 H6A 120.9 . . ?
C6 C7 C2 120.39(12) . . ?
C6 C7 H7A 119.8 . . ?
C2 C7 H7A 119.8 . . ?
O2 C8 N1 112.84(11) . . ?
O2 C8 S1 126.31(10) . . ?
N1 C8 S1 120.85(10) . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

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
C8 N1 C1 O1 -7.8(2) . . . . ?
C8 N1 C1 C2 173.65(11) . . . . ?
O1 C1 C2 C7 160.00(13) . . . . ?
N1 C1 C2 C7 -21.39(17) . . . . ?
O1 C1 C2 C3 -19.85(18) . . . . ?
N1 C1 C2 C3 158.76(12) . . . . ?
C7 C2 C3 C4 2.33(19) . . . . ?
C1 C2 C3 C4 -177.82(12) . . . . ?
C2 C3 C4 C5 -1.8(2) . . . . ?
C3 C4 C5 F1 179.29(12) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
F1 C5 C6 C7 -177.87(12) . . . . ?
C4 C5 C6 C7 1.7(2) . . . . ?
C5 C6 C7 C2 -1.1(2) . . . . ?
C3 C2 C7 C6 -0.87(19) . . . . ?
C1 C2 C7 C6 179.28(12) . . . . ?
C9 O2 C8 N1 -177.56(11) . . . . ?
C9 O2 C8 S1 2.05(17) . . . . ?
C1 N1 C8 O2 9.87(19) . . . . ?
C1 N1 C8 S1 -169.77(11) . . . . ?

_refine_diff_density_max         0.378
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-4

