# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

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

data_231128b
_database_code_depnum_ccdc_archive 'CCDC 2311019'
loop_
_audit_author_name
_audit_author_address
A
;nanjing university
China
;
_audit_update_record             
;
2023-11-29 deposited with the CCDC.	2024-02-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H9 N O2'
_chemical_formula_weight         163.17

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'

_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                   7.2336(8)
_cell_length_b                   10.6828(11)
_cell_length_c                   10.9368(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.791(4)
_cell_angle_gamma                90.00
_cell_volume                     827.31(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1213
_cell_measurement_theta_min      2.696
_cell_measurement_theta_max      27.382

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9680
_exptl_absorpt_correction_T_max  0.9898
_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            1442
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0748
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         25.02
_reflns_number_total             1442
_reflns_number_gt                1054
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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)+(0.0834P)²+0.2585P] 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         1442
_refine_ls_number_parameters     112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1081
_refine_ls_R_factor_gt           0.0795
_refine_ls_wR_factor_ref         0.1982
_refine_ls_wR_factor_gt          0.1824
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_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
N1 N 0.9526(4) 0.1610(2) 0.0350(3) 0.0535(8) Uani 1 1 d . . .
H1 H 1.0521 0.1245 0.0210 0.064 Uiso 1 1 calc R . .
O1 O 0.7417(4) 0.0036(2) -0.0275(3) 0.0596(8) Uani 1 1 d . . .
O2 O 0.5449(4) 0.1593(2) 0.1296(2) 0.0545(7) Uani 1 1 d . . .
H2 H 0.4580 0.1139 0.0957 0.082 Uiso 1 1 calc R . .
C1 C 0.7806(5) 0.1111(3) 0.0100(3) 0.0468(8) Uani 1 1 d . . .
C2 C 0.6396(5) 0.2081(3) 0.0379(3) 0.0462(8) Uani 1 1 d . . .
C3 C 0.7681(5) 0.3130(3) 0.0931(3) 0.0461(9) Uani 1 1 d . . .
C4 C 0.9513(5) 0.2820(3) 0.0877(3) 0.0481(9) Uani 1 1 d . . .
C5 C 1.1009(6) 0.3592(4) 0.1304(4) 0.0608(10) Uani 1 1 d . . .
H5 H 1.2238 0.3359 0.1276 0.073 Uiso 1 1 calc R . .
C6 C 1.0611(7) 0.4737(4) 0.1782(4) 0.0681(12) Uani 1 1 d . . .
H6 H 1.1594 0.5292 0.2071 0.082 Uiso 1 1 calc R . .
C7 C 0.8799(7) 0.5072(3) 0.1840(4) 0.0678(12) Uani 1 1 d . . .
H7 H 0.8572 0.5845 0.2170 0.081 Uiso 1 1 calc R . .
C8 C 0.7311(6) 0.4271(3) 0.1412(3) 0.0591(10) Uani 1 1 d . . .
H8 H 0.6082 0.4498 0.1447 0.071 Uiso 1 1 calc R . .
C9 C 0.5024(6) 0.2422(3) -0.0807(3) 0.0629(11) Uani 1 1 d . . .
H9A H 0.4329 0.1691 -0.1143 0.094 Uiso 1 1 calc R . .
H9B H 0.5706 0.2744 -0.1405 0.094 Uiso 1 1 calc R . .
H9C H 0.4163 0.3047 -0.0629 0.094 Uiso 1 1 calc R . .


_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
N1 C1 1.330(5) . ?
N1 C4 1.415(4) . ?
N1 H1 0.8600 . ?
O1 C1 1.232(4) . ?
O2 C2 1.423(4) . ?
O2 H2 0.8200 . ?
C1 C2 1.528(4) . ?
C2 C3 1.502(5) . ?
C2 C9 1.509(5) . ?
C3 C8 1.375(5) . ?
C3 C4 1.379(5) . ?
C4 C5 1.365(5) . ?
C5 C6 1.383(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.373(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.380(6) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

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
C1 N1 C4 111.5(3) . . ?
C1 N1 H1 124.2 . . ?
C4 N1 H1 124.2 . . ?
C2 O2 H2 109.5 . . ?
O1 C1 N1 125.6(3) . . ?
O1 C1 C2 125.6(3) . . ?
N1 C1 C2 108.8(3) . . ?
O2 C2 C3 109.7(3) . . ?
O2 C2 C9 111.6(3) . . ?
C3 C2 C9 114.2(3) . . ?
O2 C2 C1 109.2(2) . . ?
C3 C2 C1 101.7(3) . . ?
C9 C2 C1 109.9(3) . . ?
C8 C3 C4 119.6(3) . . ?
C8 C3 C2 131.4(4) . . ?
C4 C3 C2 109.0(3) . . ?
C5 C4 C3 122.8(3) . . ?
C5 C4 N1 128.4(4) . . ?
C3 C4 N1 108.8(3) . . ?
C4 C5 C6 116.9(4) . . ?
C4 C5 H5 121.5 . . ?
C6 C5 H5 121.5 . . ?
C7 C6 C5 121.5(4) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 120.6(4) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C3 C8 C7 118.7(4) . . ?
C3 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C2 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C2 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
C4 N1 C1 O1 -174.3(3) . . . . ?
C4 N1 C1 C2 4.5(4) . . . . ?
O1 C1 C2 O2 57.8(4) . . . . ?
N1 C1 C2 O2 -121.0(3) . . . . ?
O1 C1 C2 C3 173.8(3) . . . . ?
N1 C1 C2 C3 -5.1(3) . . . . ?
O1 C1 C2 C9 -64.9(4) . . . . ?
N1 C1 C2 C9 116.3(3) . . . . ?
O2 C2 C3 C8 -62.3(4) . . . . ?
C9 C2 C3 C8 63.8(5) . . . . ?
C1 C2 C3 C8 -177.9(4) . . . . ?
O2 C2 C3 C4 119.4(3) . . . . ?
C9 C2 C3 C4 -114.4(3) . . . . ?
C1 C2 C3 C4 3.9(3) . . . . ?
C8 C3 C4 C5 1.3(5) . . . . ?
C2 C3 C4 C5 179.7(3) . . . . ?
C8 C3 C4 N1 -180.0(3) . . . . ?
C2 C3 C4 N1 -1.5(4) . . . . ?
C1 N1 C4 C5 176.7(4) . . . . ?
C1 N1 C4 C3 -2.0(4) . . . . ?
C3 C4 C5 C6 -1.4(5) . . . . ?
N1 C4 C5 C6 -179.9(3) . . . . ?
C4 C5 C6 C7 0.9(6) . . . . ?
C5 C6 C7 C8 -0.4(7) . . . . ?
C4 C3 C8 C7 -0.7(5) . . . . ?
C2 C3 C8 C7 -178.7(3) . . . . ?
C6 C7 C8 C3 0.2(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.060
####################################################################### 
# 
# 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_230920f
_database_code_depnum_ccdc_archive 'CCDC 2320450'
loop_
_audit_author_name
_audit_author_address
A
;nanjing university
China
;
_audit_update_record             
;
2023-12-19 deposited with the CCDC.	2024-02-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H23 F3 N2 O6 S'
_chemical_formula_weight         560.53

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           Orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   15.0600(14)
_cell_length_b                   17.7122(16)
_cell_length_c                   9.6717(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2579.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3170
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      22.182

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1160
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9479
_exptl_absorpt_correction_T_max  0.9624
_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            12126
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_av_sigmaI/netI    0.0786
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         25.02
_reflns_number_total             4035
_reflns_number_gt                3028
_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)+(0.0304P)²+2.3404P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.15(15)
_refine_ls_number_reflns         4035
_refine_ls_number_parameters     354
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1370
_refine_ls_wR_factor_gt          0.1200
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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 -0.0267(3) 0.4314(2) 0.1642(7) 0.123(2) Uani 1 1 d . . .
F2 F 0.0355(3) 0.4755(3) -0.0110(6) 0.1301(19) Uani 1 1 d . . .
F3 F 0.0936(3) 0.3854(2) 0.0879(7) 0.131(2) Uani 1 1 d . . .
N1 N 0.4082(2) 0.56186(19) 0.2878(4) 0.0355(9) Uani 1 1 d . . .
N2 N 0.2665(2) 0.6248(2) 0.2418(4) 0.0343(9) Uani 1 1 d . . .
O1 O 0.2999(2) 0.4980(2) 0.3986(5) 0.0635(12) Uani 1 1 d . . .
O2 O 0.26271(19) 0.67292(19) 0.4532(4) 0.0466(9) Uani 1 1 d . . .
O3 O 0.13855(18) 0.62747(19) 0.3630(4) 0.0488(10) Uani 1 1 d . . .
O4 O 0.1840(2) 0.51201(18) 0.1461(5) 0.0551(11) Uani 1 1 d . . .
O5 O 0.1469(2) 0.6365(2) 0.0687(4) 0.0568(10) Uani 1 1 d . . .
O6 O 0.2889(2) 0.5769(2) 0.0104(5) 0.0658(12) Uani 1 1 d . . .
S1 S 0.21891(7) 0.59107(7) 0.10274(15) 0.0438(3) Uani 1 1 d . . .
C1 C 0.2141(3) 0.6404(3) 0.3580(5) 0.0364(11) Uani 1 1 d . . .
C2 C 0.3603(3) 0.6259(2) 0.2497(5) 0.0330(11) Uani 1 1 d . . .
C3 C 0.4143(3) 0.6834(2) 0.2225(5) 0.0342(11) Uani 1 1 d . . .
C4 C 0.5018(3) 0.6574(2) 0.2504(5) 0.0329(11) Uani 1 1 d . . .
C5 C 0.4974(3) 0.5820(3) 0.2894(5) 0.0357(11) Uani 1 1 d . . .
C6 C 0.5722(3) 0.5421(3) 0.3256(6) 0.0417(12) Uani 1 1 d . . .
H6 H 0.5688 0.4917 0.3523 0.050 Uiso 1 1 calc R . .
C7 C 0.6513(3) 0.5790(3) 0.3210(6) 0.0483(14) Uani 1 1 d . . .
H7 H 0.7028 0.5529 0.3439 0.058 Uiso 1 1 calc R . .
C8 C 0.6573(3) 0.6534(3) 0.2835(6) 0.0474(14) Uani 1 1 d . . .
H8 H 0.7127 0.6766 0.2820 0.057 Uiso 1 1 calc R . .
C9 C 0.5837(3) 0.6941(3) 0.2484(6) 0.0415(12) Uani 1 1 d . . .
H9 H 0.5881 0.7447 0.2239 0.050 Uiso 1 1 calc R . .
C10 C 0.3697(3) 0.4961(3) 0.3405(6) 0.0405(12) Uani 1 1 d . . .
C11 C 0.4156(3) 0.4253(2) 0.3086(6) 0.0398(12) Uani 1 1 d . . .
C12 C 0.4118(3) 0.3677(3) 0.4052(7) 0.0497(14) Uani 1 1 d . . .
H12 H 0.3840 0.3753 0.4899 0.060 Uiso 1 1 calc R . .
C13 C 0.4494(4) 0.3000(3) 0.3744(9) 0.0662(19) Uani 1 1 d . . .
H13 H 0.4484 0.2615 0.4400 0.079 Uiso 1 1 calc R . .
C14 C 0.4880(4) 0.2874(3) 0.2507(9) 0.0685(18) Uani 1 1 d . . .
H14 H 0.5137 0.2408 0.2317 0.082 Uiso 1 1 calc R . .
C15 C 0.4893(4) 0.3432(3) 0.1535(8) 0.0689(18) Uani 1 1 d . . .
H15 H 0.5146 0.3340 0.0674 0.083 Uiso 1 1 calc R . .
C16 C 0.4535(4) 0.4127(3) 0.1816(6) 0.0549(14) Uani 1 1 d . . .
H16 H 0.4550 0.4508 0.1155 0.066 Uiso 1 1 calc R . .
C17 C 0.3896(3) 0.7588(2) 0.1726(6) 0.0348(11) Uani 1 1 d . . .
C18 C 0.3468(3) 0.7678(3) 0.0495(6) 0.0457(13) Uani 1 1 d . . .
H18 H 0.3325 0.7257 -0.0034 0.055 Uiso 1 1 calc R . .
C19 C 0.3244(3) 0.8386(3) 0.0029(6) 0.0518(14) Uani 1 1 d . . .
H19 H 0.2953 0.8443 -0.0812 0.062 Uiso 1 1 calc R . .
C20 C 0.3448(3) 0.9000(3) 0.0797(7) 0.0533(15) Uani 1 1 d . . .
H20 H 0.3299 0.9479 0.0483 0.064 Uiso 1 1 calc R . .
C21 C 0.3870(3) 0.8916(3) 0.2024(7) 0.0525(16) Uani 1 1 d . . .
H21 H 0.4000 0.9338 0.2558 0.063 Uiso 1 1 calc R . .
C22 C 0.4109(3) 0.8207(3) 0.2490(6) 0.0452(13) Uani 1 1 d . . .
H22 H 0.4413 0.8153 0.3321 0.054 Uiso 1 1 calc R . .
C23 C 0.2184(4) 0.6897(4) 0.5842(7) 0.0665(17) Uani 1 1 d . . .
H23 H 0.1542 0.6938 0.5695 0.080 Uiso 1 1 calc R . .
C24 C 0.2543(4) 0.7630(4) 0.6306(8) 0.092(3) Uani 1 1 d . . .
H24A H 0.3176 0.7593 0.6401 0.138 Uiso 1 1 calc R . .
H24B H 0.2285 0.7761 0.7180 0.138 Uiso 1 1 calc R . .
H24C H 0.2401 0.8011 0.5636 0.138 Uiso 1 1 calc R . .
C25 C 0.2373(6) 0.6280(5) 0.6800(9) 0.115(3) Uani 1 1 d . . .
H25A H 0.2151 0.5816 0.6424 0.172 Uiso 1 1 calc R . .
H25B H 0.2089 0.6379 0.7670 0.172 Uiso 1 1 calc R . .
H25C H 0.3003 0.6241 0.6935 0.172 Uiso 1 1 calc R . .
C26 C 0.0980(4) 0.5008(3) 0.1975(7) 0.0672(18) Uani 1 1 d . . .
H26A H 0.0657 0.5482 0.1961 0.081 Uiso 1 1 calc R . .
H26B H 0.1012 0.4835 0.2925 0.081 Uiso 1 1 calc R . .
C27 C 0.0516(4) 0.4455(4) 0.1144(10) 0.077(2) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C27 1.298(7) . ?
F2 C27 1.346(10) . ?
F3 C27 1.264(7) . ?
N1 C5 1.390(5) . ?
N1 C2 1.394(5) . ?
N1 C10 1.398(6) . ?
N2 C1 1.401(6) . ?
N2 C2 1.414(5) . ?
N2 S1 1.637(4) . ?
O1 C10 1.193(5) . ?
O2 C1 1.310(6) . ?
O2 C23 1.462(7) . ?
O3 C1 1.162(5) . ?
O4 C26 1.401(6) . ?
O4 S1 1.553(4) . ?
O5 S1 1.390(4) . ?
O6 S1 1.404(4) . ?
C2 C3 1.330(6) . ?
C3 C4 1.423(6) . ?
C3 C17 1.467(6) . ?
C4 C5 1.388(6) . ?
C4 C9 1.394(6) . ?
C5 C6 1.376(6) . ?
C6 C7 1.359(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.369(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.365(7) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.466(6) . ?
C11 C16 1.373(8) . ?
C11 C12 1.383(7) . ?
C12 C13 1.360(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.349(10) . ?
C13 H13 0.9300 . ?
C14 C15 1.364(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.371(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C22 1.360(7) . ?
C17 C18 1.364(7) . ?
C18 C19 1.374(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.352(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.354(8) . ?
C20 H20 0.9300 . ?
C21 C22 1.382(6) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C25 1.460(11) . ?
C23 C24 1.476(9) . ?
C23 H23 0.9800 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.447(8) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?

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
C5 N1 C2 107.1(3) . . ?
C5 N1 C10 127.7(4) . . ?
C2 N1 C10 124.0(3) . . ?
C1 N2 C2 121.1(4) . . ?
C1 N2 S1 119.0(3) . . ?
C2 N2 S1 119.1(3) . . ?
C1 O2 C23 116.3(4) . . ?
C26 O4 S1 122.4(3) . . ?
O5 S1 O6 122.6(3) . . ?
O5 S1 O4 108.8(2) . . ?
O6 S1 O4 105.3(2) . . ?
O5 S1 N2 109.0(2) . . ?
O6 S1 N2 105.0(2) . . ?
O4 S1 N2 104.8(2) . . ?
O3 C1 O2 127.2(5) . . ?
O3 C1 N2 123.1(5) . . ?
O2 C1 N2 109.6(4) . . ?
C3 C2 N1 111.0(3) . . ?
C3 C2 N2 127.6(4) . . ?
N1 C2 N2 121.3(4) . . ?
C2 C3 C4 106.3(4) . . ?
C2 C3 C17 127.4(4) . . ?
C4 C3 C17 126.3(4) . . ?
C5 C4 C9 119.6(4) . . ?
C5 C4 C3 108.6(4) . . ?
C9 C4 C3 131.8(4) . . ?
C6 C5 C4 121.6(4) . . ?
C6 C5 N1 131.4(4) . . ?
C4 C5 N1 106.9(3) . . ?
C7 C6 C5 117.5(4) . . ?
C7 C6 H6 121.3 . . ?
C5 C6 H6 121.3 . . ?
C6 C7 C8 122.0(4) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 H7 119.0 . . ?
C9 C8 C7 121.3(4) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C4 117.9(4) . . ?
C8 C9 H9 121.0 . . ?
C4 C9 H9 121.0 . . ?
O1 C10 N1 120.9(4) . . ?
O1 C10 C11 122.7(4) . . ?
N1 C10 C11 116.1(4) . . ?
C16 C11 C12 120.2(5) . . ?
C16 C11 C10 121.5(5) . . ?
C12 C11 C10 118.0(5) . . ?
C13 C12 C11 119.0(6) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C14 C13 C12 121.3(6) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 119.8(6) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C16 120.6(7) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C11 119.1(6) . . ?
C15 C16 H16 120.5 . . ?
C11 C16 H16 120.5 . . ?
C22 C17 C18 119.4(4) . . ?
C22 C17 C3 119.7(5) . . ?
C18 C17 C3 120.9(5) . . ?
C17 C18 C19 120.6(5) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C20 C19 C18 119.9(5) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 120.0(5) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C22 120.5(5) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C17 C22 C21 119.6(5) . . ?
C17 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C25 C23 O2 108.0(6) . . ?
C25 C23 C24 113.2(7) . . ?
O2 C23 C24 106.0(5) . . ?
C25 C23 H23 109.9 . . ?
O2 C23 H23 109.9 . . ?
C24 C23 H23 109.9 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O4 C26 C27 110.2(5) . . ?
O4 C26 H26A 109.6 . . ?
C27 C26 H26A 109.6 . . ?
O4 C26 H26B 109.6 . . ?
C27 C26 H26B 109.6 . . ?
H26A C26 H26B 108.1 . . ?
F3 C27 F1 111.6(6) . . ?
F3 C27 F2 103.9(7) . . ?
F1 C27 F2 104.3(6) . . ?
F3 C27 C26 116.1(6) . . ?
F1 C27 C26 111.2(6) . . ?
F2 C27 C26 108.7(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
C26 O4 S1 O5 -24.5(5) . . . . ?
C26 O4 S1 O6 -157.6(5) . . . . ?
C26 O4 S1 N2 92.0(5) . . . . ?
C1 N2 S1 O5 50.9(4) . . . . ?
C2 N2 S1 O5 -139.2(4) . . . . ?
C1 N2 S1 O6 -176.1(3) . . . . ?
C2 N2 S1 O6 -6.2(4) . . . . ?
C1 N2 S1 O4 -65.4(4) . . . . ?
C2 N2 S1 O4 104.5(3) . . . . ?
C23 O2 C1 O3 4.9(8) . . . . ?
C23 O2 C1 N2 -177.2(4) . . . . ?
C2 N2 C1 O3 -166.1(5) . . . . ?
S1 N2 C1 O3 3.6(6) . . . . ?
C2 N2 C1 O2 15.8(6) . . . . ?
S1 N2 C1 O2 -174.5(3) . . . . ?
C5 N1 C2 C3 2.4(6) . . . . ?
C10 N1 C2 C3 170.8(5) . . . . ?
C5 N1 C2 N2 -178.3(4) . . . . ?
C10 N1 C2 N2 -9.9(7) . . . . ?
C1 N2 C2 C3 -93.0(6) . . . . ?
S1 N2 C2 C3 97.3(6) . . . . ?
C1 N2 C2 N1 87.8(5) . . . . ?
S1 N2 C2 N1 -81.9(5) . . . . ?
N1 C2 C3 C4 -2.8(6) . . . . ?
N2 C2 C3 C4 177.9(5) . . . . ?
N1 C2 C3 C17 176.6(5) . . . . ?
N2 C2 C3 C17 -2.6(9) . . . . ?
C2 C3 C4 C5 2.3(6) . . . . ?
C17 C3 C4 C5 -177.2(5) . . . . ?
C2 C3 C4 C9 -175.6(5) . . . . ?
C17 C3 C4 C9 5.0(9) . . . . ?
C9 C4 C5 C6 -0.5(8) . . . . ?
C3 C4 C5 C6 -178.6(5) . . . . ?
C9 C4 C5 N1 177.3(5) . . . . ?
C3 C4 C5 N1 -0.8(5) . . . . ?
C2 N1 C5 C6 176.6(5) . . . . ?
C10 N1 C5 C6 8.7(9) . . . . ?
C2 N1 C5 C4 -0.9(5) . . . . ?
C10 N1 C5 C4 -168.7(5) . . . . ?
C4 C5 C6 C7 -0.4(8) . . . . ?
N1 C5 C6 C7 -177.6(5) . . . . ?
C5 C6 C7 C8 0.8(8) . . . . ?
C6 C7 C8 C9 -0.3(9) . . . . ?
C7 C8 C9 C4 -0.6(8) . . . . ?
C5 C4 C9 C8 1.0(7) . . . . ?
C3 C4 C9 C8 178.6(5) . . . . ?
C5 N1 C10 O1 140.7(5) . . . . ?
C2 N1 C10 O1 -25.3(8) . . . . ?
C5 N1 C10 C11 -44.9(7) . . . . ?
C2 N1 C10 C11 149.1(5) . . . . ?
O1 C10 C11 C16 135.4(6) . . . . ?
N1 C10 C11 C16 -39.0(7) . . . . ?
O1 C10 C11 C12 -37.9(8) . . . . ?
N1 C10 C11 C12 147.8(5) . . . . ?
C16 C11 C12 C13 2.7(8) . . . . ?
C10 C11 C12 C13 176.1(5) . . . . ?
C11 C12 C13 C14 -1.7(9) . . . . ?
C12 C13 C14 C15 -0.4(10) . . . . ?
C13 C14 C15 C16 1.6(10) . . . . ?
C14 C15 C16 C11 -0.6(9) . . . . ?
C12 C11 C16 C15 -1.6(8) . . . . ?
C10 C11 C16 C15 -174.7(5) . . . . ?
C2 C3 C17 C22 120.8(6) . . . . ?
C4 C3 C17 C22 -59.8(7) . . . . ?
C2 C3 C17 C18 -60.1(7) . . . . ?
C4 C3 C17 C18 119.2(5) . . . . ?
C22 C17 C18 C19 -0.5(7) . . . . ?
C3 C17 C18 C19 -179.6(5) . . . . ?
C17 C18 C19 C20 -0.2(8) . . . . ?
C18 C19 C20 C21 -0.2(9) . . . . ?
C19 C20 C21 C22 1.2(8) . . . . ?
C18 C17 C22 C21 1.4(7) . . . . ?
C3 C17 C22 C21 -179.5(4) . . . . ?
C20 C21 C22 C17 -1.8(8) . . . . ?
C1 O2 C23 C25 96.0(6) . . . . ?
C1 O2 C23 C24 -142.4(5) . . . . ?
S1 O4 C26 C27 123.6(6) . . . . ?
O4 C26 C27 F3 47.7(10) . . . . ?
O4 C26 C27 F1 176.8(6) . . . . ?
O4 C26 C27 F2 -68.9(7) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.054
