# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cd15191
_database_code_depnum_ccdc_archive 'CCDC 1476608'
_audit_update_record             
;
2016-04-26 deposited with the CCDC.
2016-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H10 N2 S'
_chemical_formula_weight         202.27

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   9.3748(16)
_cell_length_b                   7.8979(13)
_cell_length_c                   26.980(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1997.6(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2456
_cell_measurement_theta_min      5.292
_cell_measurement_theta_max      47.317

_exptl_crystal_description       prismatic
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.282
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6893
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11031
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.510
_diffrn_reflns_theta_max         25.992
_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             1963
_reflns_number_gt                1566
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_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)+(0.0707P)²+0.2302P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1963
_refine_ls_number_parameters     131
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1185
_refine_ls_wR_factor_gt          0.1097
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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 0.18080(6) 0.21534(7) 0.36049(2) 0.0554(2) Uani 1 1 d . . . . .
N1 N 0.43554(16) 0.1485(2) 0.40249(5) 0.0433(4) Uani 1 1 d . . . . .
N2 N 0.34178(19) -0.0197(3) 0.52622(6) 0.0675(5) Uani 1 1 d . . . . .
C1 C 0.0245(2) 0.2011(3) 0.39902(8) 0.0568(5) Uani 1 1 d . . . . .
H1A H -0.0095 0.3138 0.4071 0.068 Uiso 1 1 calc R U . . .
H1B H -0.0507 0.1418 0.3815 0.068 Uiso 1 1 calc R U . . .
C2 C 0.0617(2) 0.1070(3) 0.44587(7) 0.0529(5) Uani 1 1 d . . . . .
H2A H 0.0237 0.1662 0.4745 0.063 Uiso 1 1 calc R U . . .
H2B H 0.0211 -0.0059 0.4451 0.063 Uiso 1 1 calc R U . . .
C3 C 0.22044(19) 0.0972(2) 0.44907(6) 0.0410(4) Uani 1 1 d . . . . .
C4 C 0.29291(17) 0.1465(2) 0.40808(6) 0.0374(4) Uani 1 1 d . . . . .
C5 C 0.28851(19) 0.0332(2) 0.49163(6) 0.0464(5) Uani 1 1 d . . . . .
C6 C 0.51299(19) 0.1946(2) 0.35972(6) 0.0383(4) Uani 1 1 d . . . . .
C7 C 0.6359(2) 0.2887(2) 0.36518(7) 0.0465(5) Uani 1 1 d . . . . .
H7 H 0.6662 0.3205 0.3967 0.056 Uiso 1 1 calc R U . . .
C8 C 0.7139(2) 0.3356(3) 0.32428(7) 0.0564(5) Uani 1 1 d . . . . .
H8 H 0.7966 0.3993 0.3282 0.068 Uiso 1 1 calc R U . . .
C9 C 0.6699(2) 0.2884(3) 0.27741(8) 0.0600(6) Uani 1 1 d . . . . .
H9 H 0.7212 0.3226 0.2497 0.072 Uiso 1 1 calc R U . . .
C10 C 0.5506(2) 0.1913(3) 0.27213(7) 0.0591(6) Uani 1 1 d . . . . .
H10 H 0.5219 0.1575 0.2407 0.071 Uiso 1 1 calc R U . . .
C11 C 0.4722(2) 0.1428(2) 0.31281(6) 0.0483(4) Uani 1 1 d . . . . .
H11 H 0.3918 0.0752 0.3088 0.058 Uiso 1 1 calc R U . . .
H1 H 0.488(2) 0.122(2) 0.4287(8) 0.059(6) Uiso 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 C4 1.7460(16) . ?
S1 C1 1.800(2) . ?
N1 C4 1.346(2) . ?
N1 C6 1.411(2) . ?
N1 H1 0.89(2) . ?
N2 C5 1.138(2) . ?
C1 C2 1.507(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.493(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.355(2) . ?
C3 C5 1.408(2) . ?
C6 C7 1.379(3) . ?
C6 C11 1.384(2) . ?
C7 C8 1.375(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.381(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.363(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.375(3) . ?
C10 H10 0.9300 . ?
C11 H11 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
C4 S1 C1 92.64(9) . . ?
C4 N1 C6 127.30(14) . . ?
C4 N1 H1 117.3(14) . . ?
C6 N1 H1 115.4(14) . . ?
C2 C1 S1 109.07(14) . . ?
C2 C1 H1A 109.9 . . ?
S1 C1 H1A 109.9 . . ?
C2 C1 H1B 109.9 . . ?
S1 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
C3 C2 C1 107.73(15) . . ?
C3 C2 H2A 110.2 . . ?
C1 C2 H2A 110.2 . . ?
C3 C2 H2B 110.2 . . ?
C1 C2 H2B 110.2 . . ?
H2A C2 H2B 108.5 . . ?
C4 C3 C5 122.79(17) . . ?
C4 C3 C2 115.97(15) . . ?
C5 C3 C2 121.18(15) . . ?
N1 C4 C3 126.38(15) . . ?
N1 C4 S1 120.80(12) . . ?
C3 C4 S1 112.81(13) . . ?
N2 C5 C3 179.0(2) . . ?
C7 C6 C11 119.18(16) . . ?
C7 C6 N1 118.80(15) . . ?
C11 C6 N1 121.97(17) . . ?
C8 C7 C6 120.26(17) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 120.2(2) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C10 C9 C8 119.51(18) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 120.77(18) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C6 120.00(19) . . ?
C10 C11 H11 120.0 . . ?
C6 C11 H11 120.0 . . ?

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
C4 S1 C1 C2 -11.69(16) . . . . ?
S1 C1 C2 C3 13.7(2) . . . . ?
C1 C2 C3 C4 -10.0(2) . . . . ?
C1 C2 C3 C5 172.78(18) . . . . ?
C6 N1 C4 C3 178.05(17) . . . . ?
C6 N1 C4 S1 -3.3(2) . . . . ?
C5 C3 C4 N1 -2.8(3) . . . . ?
C2 C3 C4 N1 179.97(17) . . . . ?
C5 C3 C4 S1 178.45(15) . . . . ?
C2 C3 C4 S1 1.2(2) . . . . ?
C1 S1 C4 N1 -172.52(15) . . . . ?
C1 S1 C4 C3 6.29(15) . . . . ?
C4 N1 C6 C7 139.84(18) . . . . ?
C4 N1 C6 C11 -42.7(3) . . . . ?
C11 C6 C7 C8 2.4(3) . . . . ?
N1 C6 C7 C8 179.96(17) . . . . ?
C6 C7 C8 C9 -0.2(3) . . . . ?
C7 C8 C9 C10 -1.7(3) . . . . ?
C8 C9 C10 C11 1.3(3) . . . . ?
C9 C10 C11 C6 0.9(3) . . . . ?
C7 C6 C11 C10 -2.8(3) . . . . ?
N1 C6 C11 C10 179.74(17) . . . . ?

_refine_diff_density_max         0.288
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.045

_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_dm15574
_database_code_depnum_ccdc_archive 'CCDC 1476609'
_audit_update_record             
;
2016-04-26 deposited with the CCDC.
2016-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H11 F N2 S'
_chemical_formula_weight         294.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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                   8.4770(15)
_cell_length_b                   8.6108(14)
_cell_length_c                   10.4033(15)
_cell_angle_alpha                105.090(3)
_cell_angle_beta                 96.643(2)
_cell_angle_gamma                95.659(3)
_cell_volume                     721.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1247
_cell_measurement_theta_min      4.882
_cell_measurement_theta_max      47.677

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_F_000             304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.229
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6728
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            5332
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.050
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2843
_reflns_number_gt                1783
_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)+(0.0546P)²+0.0549P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2843
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1211
_refine_ls_wR_factor_gt          0.1049
_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 0.03567(7) 0.59338(8) 0.26379(6) 0.0749(3) Uani 1 1 d . . . . .
F1 F 0.2764(2) 0.12356(18) 0.12860(14) 0.1003(5) Uani 1 1 d . . . . .
N1 N 0.2953(2) 0.4510(2) 0.1985(2) 0.0738(6) Uani 1 1 d . . . . .
H1 H 0.3499 0.4338 0.1504 0.089 Uiso 1 1 d R U . . .
N2 N 0.3997(3) 0.6045(3) -0.0836(3) 0.0968(8) Uani 1 1 d . . . . .
C1 C 0.1937(2) 0.5548(3) 0.1755(2) 0.0579(6) Uani 1 1 d . . . . .
C2 C -0.0251(3) 0.7215(3) 0.1722(3) 0.0806(7) Uani 1 1 d . . . . .
H2 H -0.1135 0.7764 0.1858 0.097 Uiso 1 1 calc R U . . .
C3 C 0.0677(3) 0.7341(3) 0.0794(3) 0.0715(7) Uani 1 1 d . . . . .
H3 H 0.0510 0.7981 0.0209 0.086 Uiso 1 1 calc R U . . .
C4 C 0.1949(2) 0.6386(3) 0.0802(2) 0.0588(6) Uani 1 1 d . . . . .
C5 C 0.3081(3) 0.6211(3) -0.0107(3) 0.0700(7) Uani 1 1 d . . . . .
C6 C 0.2908(3) 0.3661(3) 0.2972(2) 0.0600(6) Uani 1 1 d . . . . .
C7 C 0.2836(3) 0.2009(3) 0.2613(2) 0.0684(6) Uani 1 1 d . . . . .
C8 C 0.2848(3) 0.1109(3) 0.3516(2) 0.0684(6) Uani 1 1 d . . . . .
H8 H 0.2802 -0.0013 0.3222 0.082 Uiso 1 1 calc R U . . .
C9 C 0.2928(3) 0.1880(3) 0.4878(2) 0.0588(6) Uani 1 1 d . . . . .
C10 C 0.2997(3) 0.3556(3) 0.5267(2) 0.0632(6) Uani 1 1 d . . . . .
H10 H 0.3043 0.4097 0.6172 0.076 Uiso 1 1 calc R U . . .
C11 C 0.2997(3) 0.4431(3) 0.4328(2) 0.0663(6) Uani 1 1 d . . . . .
H11 H 0.3058 0.5555 0.4611 0.080 Uiso 1 1 calc R U . . .
C12 C 0.2929(3) 0.0931(3) 0.5873(2) 0.0633(6) Uani 1 1 d . . . . .
C13 C 0.3884(3) 0.1476(3) 0.7116(3) 0.0797(7) Uani 1 1 d . . . . .
H13 H 0.4561 0.2454 0.7327 0.096 Uiso 1 1 calc R U . . .
C14 C 0.3850(4) 0.0600(5) 0.8038(3) 0.1007(10) Uani 1 1 d . . . . .
H14 H 0.4506 0.0982 0.8866 0.121 Uiso 1 1 calc R U . . .
C15 C 0.2861(5) -0.0828(5) 0.7751(4) 0.1137(12) Uani 1 1 d . . . . .
H15 H 0.2836 -0.1418 0.8382 0.136 Uiso 1 1 calc R U . . .
C16 C 0.1906(5) -0.1391(4) 0.6535(4) 0.1085(11) Uani 1 1 d . . . . .
H16 H 0.1231 -0.2368 0.6336 0.130 Uiso 1 1 calc R U . . .
C17 C 0.1938(4) -0.0515(3) 0.5600(3) 0.0870(8) Uani 1 1 d . . . . .
H17 H 0.1281 -0.0908 0.4773 0.104 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 C2 1.713(3) . ?
S1 C1 1.721(2) . ?
F1 C7 1.359(2) . ?
N1 C1 1.347(3) . ?
N1 C6 1.409(3) . ?
N1 H1 0.7180 . ?
N2 C5 1.140(3) . ?
C1 C4 1.370(3) . ?
C2 C3 1.332(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.420(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.415(3) . ?
C6 C7 1.366(3) . ?
C6 C11 1.383(3) . ?
C7 C8 1.365(3) . ?
C8 C9 1.390(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.387(3) . ?
C9 C12 1.477(3) . ?
C10 C11 1.380(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C17 1.375(3) . ?
C12 C13 1.383(3) . ?
C13 C14 1.368(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.361(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.363(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.379(4) . ?
C16 H16 0.9300 . ?
C17 H17 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 S1 C1 91.34(12) . . ?
C1 N1 C6 125.74(18) . . ?
C1 N1 H1 114.0 . . ?
C6 N1 H1 119.9 . . ?
N1 C1 C4 127.04(19) . . ?
N1 C1 S1 122.28(17) . . ?
C4 C1 S1 110.64(17) . . ?
C3 C2 S1 112.9(2) . . ?
C3 C2 H2 123.6 . . ?
S1 C2 H2 123.6 . . ?
C2 C3 C4 112.3(2) . . ?
C2 C3 H3 123.9 . . ?
C4 C3 H3 123.9 . . ?
C1 C4 C5 121.8(2) . . ?
C1 C4 C3 112.9(2) . . ?
C5 C4 C3 125.3(2) . . ?
N2 C5 C4 178.8(3) . . ?
C7 C6 C11 117.1(2) . . ?
C7 C6 N1 120.0(2) . . ?
C11 C6 N1 122.8(2) . . ?
F1 C7 C8 118.8(2) . . ?
F1 C7 C6 117.8(2) . . ?
C8 C7 C6 123.4(2) . . ?
C7 C8 C9 119.6(2) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 118.1(2) . . ?
C10 C9 C12 121.3(2) . . ?
C8 C9 C12 120.6(2) . . ?
C11 C10 C9 120.9(2) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C6 121.0(2) . . ?
C10 C11 H11 119.5 . . ?
C6 C11 H11 119.5 . . ?
C17 C12 C13 117.9(2) . . ?
C17 C12 C9 120.5(2) . . ?
C13 C12 C9 121.6(2) . . ?
C14 C13 C12 121.0(3) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C15 C14 C13 120.3(3) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 119.8(3) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C17 120.1(3) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C12 C17 C16 120.8(3) . . ?
C12 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?

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 N1 C1 C4 -179.8(2) . . . . ?
C6 N1 C1 S1 -2.2(3) . . . . ?
C2 S1 C1 N1 -178.3(2) . . . . ?
C2 S1 C1 C4 -0.31(17) . . . . ?
C1 S1 C2 C3 0.4(2) . . . . ?
S1 C2 C3 C4 -0.4(3) . . . . ?
N1 C1 C4 C5 1.2(4) . . . . ?
S1 C1 C4 C5 -176.62(18) . . . . ?
N1 C1 C4 C3 178.0(2) . . . . ?
S1 C1 C4 C3 0.2(2) . . . . ?
C2 C3 C4 C1 0.1(3) . . . . ?
C2 C3 C4 C5 176.8(2) . . . . ?
C1 N1 C6 C7 125.3(3) . . . . ?
C1 N1 C6 C11 -57.3(3) . . . . ?
C11 C6 C7 F1 -179.3(2) . . . . ?
N1 C6 C7 F1 -1.9(3) . . . . ?
C11 C6 C7 C8 0.0(4) . . . . ?
N1 C6 C7 C8 177.5(2) . . . . ?
F1 C7 C8 C9 179.7(2) . . . . ?
C6 C7 C8 C9 0.3(4) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C7 C8 C9 C12 179.5(2) . . . . ?
C8 C9 C10 C11 -0.5(3) . . . . ?
C12 C9 C10 C11 179.9(2) . . . . ?
C9 C10 C11 C6 0.9(3) . . . . ?
C7 C6 C11 C10 -0.6(3) . . . . ?
N1 C6 C11 C10 -178.03(19) . . . . ?
C10 C9 C12 C17 138.5(2) . . . . ?
C8 C9 C12 C17 -41.1(3) . . . . ?
C10 C9 C12 C13 -39.8(3) . . . . ?
C8 C9 C12 C13 140.6(2) . . . . ?
C17 C12 C13 C14 0.3(4) . . . . ?
C9 C12 C13 C14 178.7(2) . . . . ?
C12 C13 C14 C15 -0.4(4) . . . . ?
C13 C14 C15 C16 0.3(5) . . . . ?
C14 C15 C16 C17 -0.2(5) . . . . ?
C13 C12 C17 C16 -0.2(4) . . . . ?
C9 C12 C17 C16 -178.6(2) . . . . ?
C15 C16 C17 C12 0.1(5) . . . . ?

_refine_diff_density_max         0.168
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.032

_shelxl_version_number           2013-4

