# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_TRY_a
_database_code_depnum_ccdc_archive 'CCDC 2209512'
loop_
_audit_author_name
_audit_author_address
'Manjeet Singh'
;Indian Institute of Science Education and Research Pune
India
;
_audit_update_record             
;
2023-07-24 deposited with the CCDC.	2023-10-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 F6 N2 O5 S2'
_chemical_formula_weight         414.30

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'
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'
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/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   5.5295(13)
_cell_length_b                   21.270(5)
_cell_length_c                   12.923(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.235(8)
_cell_angle_gamma                90
_cell_volume                     1504.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9596
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      26.95

_exptl_crystal_description       Neddle
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.830
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.451
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            71041
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_av_R_equivalents  0.1438
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.491
_diffrn_reflns_theta_max         28.360
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3763
_reflns_number_gt                2610
_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-2019/1 (Sheldrick, 2019)'
_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)+(0.1002P)²+4.0736P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0031(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3763
_refine_ls_number_parameters     216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1072
_refine_ls_R_factor_gt           0.0727
_refine_ls_wR_factor_ref         0.2050
_refine_ls_wR_factor_gt          0.1881
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 0.54336(17) 0.63985(5) 0.51423(8) 0.0253(3) Uani 1 1 d . . . . .
S2 S 0.23088(18) 0.70471(5) 0.64449(9) 0.0288(3) Uani 1 1 d . . . . .
F3 F 0.6224(5) 0.77563(12) 0.6696(2) 0.0355(6) Uani 1 1 d . . . . .
F6 F 0.1035(5) 0.63230(13) 0.4073(2) 0.0366(6) Uani 1 1 d . . . . .
F1 F 0.5436(6) 0.73260(13) 0.8101(2) 0.0439(7) Uani 1 1 d . . . . .
F2 F 0.3183(5) 0.80896(13) 0.7409(2) 0.0444(7) Uani 1 1 d . . . . .
O4 O 0.5795(6) 0.70091(15) 0.4779(2) 0.0330(7) Uani 1 1 d . . . . .
O5 O 0.7333(5) 0.59504(16) 0.5355(2) 0.0331(7) Uani 1 1 d . . . . .
O2 O 0.1466(6) 0.73595(16) 0.5498(3) 0.0392(8) Uani 1 1 d . . . . .
F4 F 0.2802(7) 0.54448(15) 0.4393(3) 0.0665(11) Uani 1 1 d . . . . .
F5 F 0.3947(6) 0.60659(19) 0.3244(2) 0.0619(10) Uani 1 1 d . . . . .
O3 O 0.0748(6) 0.68390(16) 0.7152(3) 0.0444(9) Uani 1 1 d . . . . .
N2 N 0.4035(6) 0.64317(16) 0.6212(3) 0.0249(7) Uani 1 1 d . . . . .
O1 O 0.9383(12) 0.42738(17) 0.9222(3) 0.0759(15) Uani 1 1 d . . . . .
C10 C 0.4465(8) 0.75876(19) 0.7215(3) 0.0284(9) Uani 1 1 d . . . . .
C6 C 0.4336(7) 0.59111(19) 0.6944(3) 0.0272(9) Uani 1 1 d . . . . .
C7 C 0.6461(8) 0.58602(19) 0.7645(3) 0.0281(9) Uani 1 1 d . . . . .
H7 H 0.768088 0.616121 0.764569 0.034 Uiso 1 1 calc R U . . .
C8 C 0.6789(11) 0.5366(2) 0.8346(3) 0.0380(11) Uani 1 1 d . . . . .
H8 H 0.822989 0.532850 0.881077 0.046 Uiso 1 1 calc R U . . .
C9 C 0.3130(8) 0.6028(2) 0.4161(4) 0.0334(10) Uani 1 1 d . . . . .
C3 C 0.4918(17) 0.4923(2) 0.8344(4) 0.0691(17) Uani 1 1 d . . . . .
C5 C 0.2464(9) 0.5474(2) 0.6939(4) 0.0419(12) Uani 1 1 d . . . . .
H5 H 0.103056 0.551159 0.646981 0.050 Uiso 1 1 calc R U . . .
N1 N 0.5207(13) 0.4410(2) 0.9060(3) 0.0690(19) Uani 1 1 d . . . . .
H1 H 0.390269 0.426041 0.925761 0.083 Uiso 1 1 calc R U . . .
C4 C 0.2770(11) 0.4988(2) 0.7636(5) 0.0502(16) Uani 1 1 d . . . . .
H4 H 0.152642 0.469366 0.764021 0.060 Uiso 1 1 calc R U . . .
C2 C 0.740(2) 0.4131(3) 0.9468(5) 0.0759(15) Uani 1 1 d . . . . .
C1 C 0.7116(16) 0.3621(2) 1.0260(4) 0.0691(17) Uani 1 1 d . . . . .
H1A H 0.817873 0.327598 1.016309 0.104 Uiso 1 1 calc R U . . .
H1B H 0.545254 0.347761 1.016535 0.104 Uiso 1 1 calc R U . . .
H1C H 0.753214 0.378696 1.095375 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 O4 1.405(3) . ?
S1 O5 1.416(3) . ?
S1 N2 1.679(3) . ?
S1 C9 1.841(5) . ?
S2 O3 1.415(3) . ?
S2 O2 1.411(4) . ?
S2 N2 1.673(3) . ?
S2 C10 1.842(4) . ?
F3 C10 1.308(5) . ?
F6 C9 1.308(5) . ?
F1 C10 1.316(5) . ?
F2 C10 1.325(5) . ?
F4 C9 1.296(6) . ?
F5 C9 1.329(5) . ?
N2 C6 1.450(6) . ?
O1 C2 1.220(10) . ?
C6 C7 1.382(6) . ?
C6 C5 1.391(6) . ?
C7 C8 1.383(6) . ?
C8 C3 1.399(8) . ?
C3 C4 1.398(10) . ?
C3 N1 1.425(7) . ?
C5 C4 1.366(8) . ?
N1 C2 1.387(11) . ?
C2 C1 1.516(7) . ?

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
O4 S1 O5 123.4(2) . . ?
O4 S1 N2 109.90(18) . . ?
O5 S1 N2 106.55(18) . . ?
O4 S1 C9 106.4(2) . . ?
O5 S1 C9 105.5(2) . . ?
N2 S1 C9 103.32(19) . . ?
O3 S2 O2 123.4(2) . . ?
O3 S2 N2 106.7(2) . . ?
O2 S2 N2 109.79(19) . . ?
O3 S2 C10 104.7(2) . . ?
O2 S2 C10 106.4(2) . . ?
N2 S2 C10 104.11(19) . . ?
C6 N2 S2 119.7(3) . . ?
C6 N2 S1 118.8(3) . . ?
S2 N2 S1 121.5(2) . . ?
F3 C10 F1 108.7(4) . . ?
F3 C10 F2 109.5(3) . . ?
F1 C10 F2 109.8(4) . . ?
F3 C10 S2 111.4(3) . . ?
F1 C10 S2 111.0(3) . . ?
F2 C10 S2 106.4(3) . . ?
C7 C6 C5 120.8(4) . . ?
C7 C6 N2 119.7(3) . . ?
C5 C6 N2 119.5(4) . . ?
C6 C7 C8 120.6(4) . . ?
C7 C8 C3 118.9(6) . . ?
F4 C9 F6 109.1(4) . . ?
F4 C9 F5 109.9(4) . . ?
F6 C9 F5 107.7(4) . . ?
F4 C9 S1 110.9(3) . . ?
F6 C9 S1 111.8(3) . . ?
F5 C9 S1 107.4(3) . . ?
C8 C3 C4 119.6(5) . . ?
C8 C3 N1 120.0(7) . . ?
C4 C3 N1 120.4(6) . . ?
C4 C5 C6 118.8(5) . . ?
C2 N1 C3 125.8(6) . . ?
C5 C4 C3 121.3(5) . . ?
O1 C2 N1 124.4(5) . . ?
O1 C2 C1 122.6(8) . . ?
N1 C2 C1 113.0(7) . . ?

_refine_diff_density_max         2.524
_refine_diff_density_min         -1.002
_refine_diff_density_rms         0.112

####################################################################### 
# 
# 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_TRY6_a
_database_code_depnum_ccdc_archive 'CCDC 2209513'
loop_
_audit_author_name
_audit_author_address
'Saikat Pahan'
;IISER PUNE 
India
;
_audit_update_record             
;
2023-07-23 deposited with the CCDC.	2023-10-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H8 F N O2'
_chemical_formula_weight         205.18

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   11.206(3)
_cell_length_b                   9.424(3)
_cell_length_c                   18.834(6)
_cell_angle_alpha                90
_cell_angle_beta                 106.890(9)
_cell_angle_gamma                90
_cell_volume                     1903.2(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    3140
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      28.12

_exptl_crystal_description       Rod
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.112
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9792
_diffrn_reflns_av_unetI/netI     0.0755
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.260
_diffrn_reflns_theta_max         28.323
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.773
_diffrn_measured_fraction_theta_full 0.716
_diffrn_reflns_Laue_measured_fraction_max 0.773
_diffrn_reflns_Laue_measured_fraction_full 0.716
_diffrn_reflns_point_group_measured_fraction_max 0.773
_diffrn_reflns_point_group_measured_fraction_full 0.716
_reflns_number_total             1838
_reflns_number_gt                1288
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0345P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0034(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1838
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.0931
_refine_ls_wR_factor_gt          0.0864
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_restrained_S_all      0.935
_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
F1 F 0.56535(8) 0.68682(10) 0.60633(5) 0.0206(3) Uani 1 1 d . . . . .
O3 O 0.42357(10) 0.89004(12) 0.39472(6) 0.0170(3) Uani 1 1 d . . . . .
O1 O 0.20461(10) 0.61342(12) 0.38824(6) 0.0194(3) Uani 1 1 d . . . . .
N1 N 0.37806(11) 0.68048(14) 0.48110(7) 0.0148(3) Uani 1 1 d . . . . .
H1 H 0.433960 0.745710 0.493395 0.018 Uiso 1 1 calc R U . . .
C7 C 0.48070(14) 0.57936(17) 0.59976(9) 0.0145(3) Uani 1 1 d . . . . .
C5 C 0.29554(13) 0.69086(16) 0.41171(8) 0.0142(3) Uani 1 1 d . . . . .
C11 C 0.29520(15) 0.46598(16) 0.52802(9) 0.0171(4) Uani 1 1 d . . . . .
H11 H 0.227097 0.459566 0.485837 0.020 Uiso 1 1 calc R U . . .
C13 C 0.27099(14) 0.83246(17) 0.29258(9) 0.0172(4) Uani 1 1 d . . . . .
H13 H 0.202196 0.787929 0.260496 0.021 Uiso 1 1 calc R U . . .
C8 C 0.49732(15) 0.48259(17) 0.65567(9) 0.0161(3) Uani 1 1 d . . . . .
H8 H 0.565125 0.489280 0.698001 0.019 Uiso 1 1 calc R U . . .
C4 C 0.32377(14) 0.80234(16) 0.36515(9) 0.0150(4) Uani 1 1 d . . . . .
C9 C 0.41070(14) 0.37375(17) 0.64802(9) 0.0170(4) Uani 1 1 d . . . . .
H9 H 0.419880 0.306236 0.685240 0.020 Uiso 1 1 calc R U . . .
C6 C 0.38180(14) 0.57525(16) 0.53456(9) 0.0135(3) Uani 1 1 d . . . . .
C2 C 0.43180(16) 0.97683(17) 0.33803(10) 0.0196(4) Uani 1 1 d . . . . .
H2 H 0.491407 1.047496 0.342316 0.024 Uiso 1 1 calc R U . . .
C3 C 0.34133(15) 0.94556(18) 0.27502(9) 0.0191(4) Uani 1 1 d . . . . .
H3 H 0.327744 0.989452 0.229132 0.023 Uiso 1 1 calc R U . . .
C10 C 0.31073(15) 0.36700(17) 0.58443(10) 0.0187(4) Uani 1 1 d . . . . .
H10 H 0.252623 0.294432 0.579420 0.022 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
F1 C7 1.3684(18) . ?
O3 C2 1.369(2) . ?
O3 C4 1.3720(18) . ?
O1 C5 1.2266(18) . ?
N1 C5 1.3675(19) . ?
N1 C6 1.405(2) . ?
N1 H1 0.8600 . ?
C7 C8 1.364(2) . ?
C7 C6 1.395(2) . ?
C5 C4 1.461(2) . ?
C11 C10 1.386(2) . ?
C11 C6 1.396(2) . ?
C11 H11 0.9300 . ?
C13 C4 1.352(2) . ?
C13 C3 1.421(2) . ?
C13 H13 0.9300 . ?
C8 C9 1.391(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.383(2) . ?
C9 H9 0.9300 . ?
C2 C3 1.350(2) . ?
C2 H2 0.9300 . ?
C3 H3 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
C2 O3 C4 105.96(12) . . ?
C5 N1 C6 127.32(13) . . ?
C5 N1 H1 116.3 . . ?
C6 N1 H1 116.3 . . ?
C8 C7 F1 119.30(13) . . ?
C8 C7 C6 123.79(15) . . ?
F1 C7 C6 116.91(14) . . ?
O1 C5 N1 124.20(15) . . ?
O1 C5 C4 120.91(14) . . ?
N1 C5 C4 114.88(13) . . ?
C10 C11 C6 119.97(14) . . ?
C10 C11 H11 120.0 . . ?
C6 C11 H11 120.0 . . ?
C4 C13 C3 106.47(14) . . ?
C4 C13 H13 126.8 . . ?
C3 C13 H13 126.8 . . ?
C7 C8 C9 118.58(14) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
C13 C4 O3 110.45(14) . . ?
C13 C4 C5 130.56(14) . . ?
O3 C4 C5 118.87(13) . . ?
C10 C9 C8 119.27(16) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C7 C6 C11 116.89(15) . . ?
C7 C6 N1 117.50(14) . . ?
C11 C6 N1 125.61(13) . . ?
C3 C2 O3 110.58(15) . . ?
C3 C2 H2 124.7 . . ?
O3 C2 H2 124.7 . . ?
C2 C3 C13 106.55(15) . . ?
C2 C3 H3 126.7 . . ?
C13 C3 H3 126.7 . . ?
C9 C10 C11 121.49(15) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?

_refine_diff_density_max         0.216
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.045

