# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1875539'
_audit_update_record             
;
2018-10-26 deposited with the CCDC.
2018-12-12 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            
4'-(4-nitrophenyl)spiro[indene-2,5'-[1,4,2]oxathiazol]-1(3H)-one-4'-oxide
_chemical_formula_moiety         'C16 H10 N2 O5 S'
_chemical_formula_sum            'C16 H10 N2 O5 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         342.32

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5520(11)
_cell_length_b                   8.2283(11)
_cell_length_c                   12.8010(18)
_cell_angle_alpha                74.726(4)
_cell_angle_beta                 86.674(5)
_cell_angle_gamma                72.819(4)
_cell_volume                     732.95(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5153
_cell_measurement_theta_min      2.6782
_cell_measurement_theta_max      26.1366
_cell_measurement_temperature    300.(2)

_exptl_crystal_description       PLATE
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.498
_exptl_crystal_size_mid          0.385
_exptl_crystal_size_min          0.184
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             352

_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_T_max  0.95

_exptl_special_details           
;
;

_diffrn_ambient_temperature      300.(2)

_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'Bruker X2S'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'doubly curved silicon crystal'

_diffrn_measurement_device_type  'Bruker SMART X2S'
_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean 8.3330

_diffrn_reflns_number            15211
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_theta_min         2.68
_diffrn_reflns_theta_max         26.40
_diffrn_reflns_theta_full        26.40
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
;

_reflns_number_total             2960
_reflns_number_gt                2275
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_gt          0.1583
_refine_ls_wR_factor_ref         0.1729
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.057
_refine_ls_number_reflns         2960
_refine_ls_number_parameters     217
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1207P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.405
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.6826(2) 0.9498(2) 0.24895(15) 0.0595(5) Uani d . . . 1 . .
S S2 0.72499(8) 0.79147(9) 0.18484(5) 0.0538(3) Uani d U . . 1 . .
C C3 0.4974(3) 0.7564(3) 0.22754(17) 0.0400(5) Uani d . . . 1 . .
C C4 0.4596(3) 0.8320(3) 0.32380(17) 0.0400(5) Uani d . . . 1 . .
N N5 0.5520(3) 0.9351(3) 0.33477(16) 0.0511(5) Uani d . . . 1 . .
O O6 0.8669(2) 0.6377(3) 0.24525(16) 0.0704(6) Uani d U . . 1 . .
C C7 0.3576(3) 0.8677(3) 0.13117(17) 0.0416(5) Uani d . . . 1 . .
C C8 0.3056(3) 0.7421(3) 0.08614(16) 0.0373(5) Uani d . . . 1 . .
C C9 0.1919(3) 0.7767(3) -0.00449(18) 0.0463(5) Uani d . . . 1 . .
H H9 0.1358 0.8916 -0.044 0.056 Uiso calc U . R 1 . .
C C10 0.1657(3) 0.6358(4) -0.0333(2) 0.0534(6) Uani d . . . 1 . .
H H10 0.0931 0.6553 -0.0941 0.064 Uiso calc U . R 1 . .
C C11 0.2462(3) 0.4651(3) 0.0272(2) 0.0515(6) Uani d . . . 1 . .
H H11 0.2251 0.372 0.0067 0.062 Uiso calc U . R 1 . .
C C12 0.3568(3) 0.4300(3) 0.11721(18) 0.0435(5) Uani d . . . 1 . .
H H12 0.4101 0.3149 0.1573 0.052 Uiso calc U . R 1 . .
C C13 0.3867(3) 0.5708(3) 0.14647(17) 0.0365(5) Uani d . . . 1 . .
C C14 0.5030(3) 0.5641(3) 0.24007(17) 0.0408(5) Uani d . . . 1 . .
H H14A 0.6291 0.4914 0.2364 0.049 Uiso calc U . R 1 . .
H H14B 0.4514 0.5172 0.3086 0.049 Uiso calc U . R 1 . .
O O15 0.3132(3) 1.0254(2) 0.10213(15) 0.0681(5) Uani d . . . 1 . .
C C16 0.3173(3) 0.8013(3) 0.40496(17) 0.0395(5) Uani d . . . 1 . .
C C17 0.1681(3) 0.7490(3) 0.38056(18) 0.0457(5) Uani d . . . 1 . .
H H17 0.1591 0.73 0.3128 0.055 Uiso calc U . R 1 . .
C C18 0.0338(3) 0.7252(3) 0.45640(19) 0.0455(5) Uani d . . . 1 . .
H H18 -0.0641 0.6876 0.4409 0.055 Uiso calc U . R 1 . .
C C19 0.0474(3) 0.7579(3) 0.55508(18) 0.0415(5) Uani d . . . 1 . .
C C20 0.1923(3) 0.8121(3) 0.58168(17) 0.0421(5) Uani d . . . 1 . .
H H20 0.1976 0.8347 0.6487 0.05 Uiso calc U . R 1 . .
C C21 0.3278(3) 0.8316(3) 0.50721(17) 0.0405(5) Uani d . . . 1 . .
H H21 0.4274 0.8651 0.5245 0.049 Uiso calc U . R 1 . .
N N22 -0.0990(3) 0.7381(3) 0.63478(16) 0.0512(5) Uani d . . . 1 . .
O O23 -0.0893(3) 0.7781(3) 0.71925(15) 0.0705(5) Uani d . . . 1 . .
O O24 -0.2223(2) 0.6847(3) 0.61144(17) 0.0702(5) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N5 . 1.439(2) ?
O1 S2 . 1.6610(19) ?
S2 O6 . 1.458(2) ?
S2 C3 . 1.854(2) ?
C3 C4 . 1.499(3) ?
C3 C14 . 1.535(3) ?
C3 C7 . 1.568(3) ?
C4 N5 . 1.284(3) ?
C4 C16 . 1.480(3) ?
C7 O15 . 1.199(3) ?
C7 C8 . 1.461(3) ?
C8 C13 . 1.389(3) ?
C8 C9 . 1.401(3) ?
C9 C10 . 1.374(3) ?
C9 H9 . 0.93 ?
C10 C11 . 1.385(4) ?
C10 H10 . 0.93 ?
C11 C12 . 1.379(3) ?
C11 H11 . 0.93 ?
C12 C13 . 1.388(3) ?
C12 H12 . 0.93 ?
C13 C14 . 1.506(3) ?
C14 H14A . 0.97 ?
C14 H14B . 0.97 ?
C16 C17 . 1.396(3) ?
C16 C21 . 1.406(3) ?
C17 C18 . 1.383(3) ?
C17 H17 . 0.93 ?
C18 C19 . 1.375(3) ?
C18 H18 . 0.93 ?
C19 C20 . 1.387(3) ?
C19 N22 . 1.476(3) ?
C20 C21 . 1.373(3) ?
C20 H20 . 0.93 ?
C21 H21 . 0.93 ?
N22 O24 . 1.222(2) ?
N22 O23 . 1.222(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N5 O1 S2 . . 114.08(12) ?
O6 S2 O1 . . 109.17(10) ?
O6 S2 C3 . . 106.93(10) ?
O1 S2 C3 . . 89.61(8) ?
C4 C3 C14 . . 119.84(17) ?
C4 C3 C7 . . 111.99(17) ?
C14 C3 C7 . . 105.57(16) ?
C4 C3 S2 . . 101.54(13) ?
C14 C3 S2 . . 110.94(14) ?
C7 C3 S2 . . 106.31(13) ?
N5 C4 C16 . . 117.70(19) ?
N5 C4 C3 . . 118.04(18) ?
C16 C4 C3 . . 124.21(17) ?
C4 N5 O1 . . 109.98(17) ?
O15 C7 C8 . . 129.7(2) ?
O15 C7 C3 . . 123.61(19) ?
C8 C7 C3 . . 106.63(17) ?
C13 C8 C9 . . 121.1(2) ?
C13 C8 C7 . . 110.56(18) ?
C9 C8 C7 . . 128.3(2) ?
C10 C9 C8 . . 118.0(2) ?
C10 C9 H9 . . 121.0 ?
C8 C9 H9 . . 121.0 ?
C9 C10 C11 . . 120.8(2) ?
C9 C10 H10 . . 119.6 ?
C11 C10 H10 . . 119.6 ?
C12 C11 C10 . . 121.6(2) ?
C12 C11 H11 . . 119.2 ?
C10 C11 H11 . . 119.2 ?
C11 C12 C13 . . 118.3(2) ?
C11 C12 H12 . . 120.8 ?
C13 C12 H12 . . 120.8 ?
C12 C13 C8 . . 120.2(2) ?
C12 C13 C14 . . 127.6(2) ?
C8 C13 C14 . . 112.23(17) ?
C13 C14 C3 . . 104.65(16) ?
C13 C14 H14A . . 110.8 ?
C3 C14 H14A . . 110.8 ?
C13 C14 H14B . . 110.8 ?
C3 C14 H14B . . 110.8 ?
H14A C14 H14B . . 108.9 ?
C17 C16 C21 . . 119.1(2) ?
C17 C16 C4 . . 121.19(19) ?
C21 C16 C4 . . 119.67(18) ?
C18 C17 C16 . . 120.5(2) ?
C18 C17 H17 . . 119.8 ?
C16 C17 H17 . . 119.8 ?
C19 C18 C17 . . 118.84(19) ?
C19 C18 H18 . . 120.6 ?
C17 C18 H18 . . 120.6 ?
C18 C19 C20 . . 122.28(19) ?
C18 C19 N22 . . 118.92(19) ?
C20 C19 N22 . . 118.8(2) ?
C21 C20 C19 . . 118.7(2) ?
C21 C20 H20 . . 120.6 ?
C19 C20 H20 . . 120.6 ?
C20 C21 C16 . . 120.54(19) ?
C20 C21 H21 . . 119.7 ?
C16 C21 H21 . . 119.7 ?
O24 N22 O23 . . 124.6(2) ?
O24 N22 C19 . . 117.9(2) ?
O23 N22 C19 . . 117.55(19) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N5 O1 S2 O6 . . . . -83.98(17) ?
N5 O1 S2 C3 . . . . 23.84(16) ?
O6 S2 C3 C4 . . . . 88.02(15) ?
O1 S2 C3 C4 . . . . -21.93(14) ?
O6 S2 C3 C14 . . . . -40.44(18) ?
O1 S2 C3 C14 . . . . -150.38(16) ?
O6 S2 C3 C7 . . . . -154.72(14) ?
O1 S2 C3 C7 . . . . 95.33(14) ?
C14 C3 C4 N5 . . . . 140.2(2) ?
C7 C3 C4 N5 . . . . -95.4(2) ?
S2 C3 C4 N5 . . . . 17.7(2) ?
C14 C3 C4 C16 . . . . -42.3(3) ?
C7 C3 C4 C16 . . . . 82.1(2) ?
S2 C3 C4 C16 . . . . -164.87(17) ?
C16 C4 N5 O1 . . . . -179.77(17) ?
C3 C4 N5 O1 . . . . -2.1(3) ?
S2 O1 N5 C4 . . . . -17.6(2) ?
C4 C3 C7 O15 . . . . 44.5(3) ?
C14 C3 C7 O15 . . . . 176.6(2) ?
S2 C3 C7 O15 . . . . -65.5(2) ?
C4 C3 C7 C8 . . . . -137.79(17) ?
C14 C3 C7 C8 . . . . -5.8(2) ?
S2 C3 C7 C8 . . . . 112.15(15) ?
O15 C7 C8 C13 . . . . -179.0(2) ?
C3 C7 C8 C13 . . . . 3.6(2) ?
O15 C7 C8 C9 . . . . 1.2(4) ?
C3 C7 C8 C9 . . . . -176.27(19) ?
C13 C8 C9 C10 . . . . -1.2(3) ?
C7 C8 C9 C10 . . . . 178.6(2) ?
C8 C9 C10 C11 . . . . 1.5(3) ?
C9 C10 C11 C12 . . . . -0.8(3) ?
C10 C11 C12 C13 . . . . 0.0(3) ?
C11 C12 C13 C8 . . . . 0.3(3) ?
C11 C12 C13 C14 . . . . -179.31(18) ?
C9 C8 C13 C12 . . . . 0.4(3) ?
C7 C8 C13 C12 . . . . -179.45(18) ?
C9 C8 C13 C14 . . . . -179.97(17) ?
C7 C8 C13 C14 . . . . 0.2(2) ?
C12 C13 C14 C3 . . . . 175.72(19) ?
C8 C13 C14 C3 . . . . -3.9(2) ?
C4 C3 C14 C13 . . . . 133.13(18) ?
C7 C3 C14 C13 . . . . 5.7(2) ?
S2 C3 C14 C13 . . . . -109.06(15) ?
N5 C4 C16 C17 . . . . 156.1(2) ?
C3 C4 C16 C17 . . . . -21.4(3) ?
N5 C4 C16 C21 . . . . -21.5(3) ?
C3 C4 C16 C21 . . . . 161.0(2) ?
C21 C16 C17 C18 . . . . -0.8(3) ?
C4 C16 C17 C18 . . . . -178.36(19) ?
C16 C17 C18 C19 . . . . 1.5(3) ?
C17 C18 C19 C20 . . . . -0.8(3) ?
C17 C18 C19 N22 . . . . 178.06(18) ?
C18 C19 C20 C21 . . . . -0.8(3) ?
N22 C19 C20 C21 . . . . -179.59(17) ?
C19 C20 C21 C16 . . . . 1.5(3) ?
C17 C16 C21 C20 . . . . -0.8(3) ?
C4 C16 C21 C20 . . . . 176.84(18) ?
C18 C19 N22 O24 . . . . 3.5(3) ?
C20 C19 N22 O24 . . . . -177.6(2) ?
C18 C19 N22 O23 . . . . -175.7(2) ?
C20 C19 N22 O23 . . . . 3.1(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C14 H14A O6 . 0.97 2.46 2.992(3) 114.1 ?



####################################################################### 
# 
# 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_I_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1875541'
_audit_update_record             
;
2018-10-26 deposited with the CCDC.
2018-12-12 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H19 N O3 S'
_chemical_formula_sum            'C20 H19 N O3 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         353.42

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   11.0131(2)
_cell_length_b                   11.9246(2)
_cell_length_c                   14.5681(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.1060(10)
_cell_angle_gamma                90
_cell_volume                     1828.55(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9859
_cell_measurement_theta_min      3.1740
_cell_measurement_theta_max      66.8361
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.421
_exptl_crystal_size_mid          0.315
_exptl_crystal_size_min          0.196
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744

_exptl_absorpt_coefficient_mu    1.721
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_T_max  0.75

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   'Incoatec Microfocus X-ray Source I\mS'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Incoatec Montel Multilayer Mirror'

_diffrn_measurement_device_type  'Bruker ACS Kappa APEX II DUO diffractometer'
_diffrn_measurement_method       'ω and φ scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            22017
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_theta_min         4.88
_diffrn_reflns_theta_max         67.22
_diffrn_reflns_theta_full        67.22
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.964
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
;

_reflns_number_total             3172
_reflns_number_gt                3041
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_gt          0.1588
_refine_ls_wR_factor_ref         0.1600
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.215
_refine_ls_number_reflns         3172
_refine_ls_number_parameters     255
_refine_ls_number_restraints     72
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0887P)²+0.8268P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.430
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.41964(19) 0.78572(18) 0.49732(12) 0.0785(6) Uani d . . . 1.0 . .
N N5 0.3296(2) 0.71608(19) 0.52498(14) 0.0690(6) Uani d . . . 1.0 . .
C C3 0.3449(2) 0.72514(18) 0.61523(15) 0.0522(5) Uani d . . . 1.0 . .
C C4 0.4502(2) 0.79876(18) 0.67220(15) 0.0495(5) Uani d . . . 1.0 . .
S S2 0.49018(6) 0.88032(5) 0.57660(5) 0.0661(3) Uani d . . . 1.0 . .
C C6 0.2635(2) 0.65840(18) 0.65886(15) 0.0511(5) Uani d . . . 1.0 . .
C C7 0.1457(2) 0.6202(2) 0.60385(18) 0.0617(6) Uani d . . . 1.0 . .
H H7 0.1159 0.6399 0.5393 0.074 Uiso calc U . R 1.0 . .
C C8 0.0722(2) 0.5535(2) 0.6434(2) 0.0671(6) Uani d . . . 1.0 . .
H H8 -0.006 0.5284 0.6046 0.08 Uiso calc U . R 1.0 . .
C C9 0.1116(2) 0.52245(19) 0.73982(18) 0.0600(6) Uani d . . D 1.0 . .
C C10 0.2296(2) 0.5622(2) 0.79431(18) 0.0632(6) Uani d . . . 1.0 . .
H H10 0.2591 0.5434 0.859 0.076 Uiso calc U . R 1.0 . .
C C11 0.3036(2) 0.6285(2) 0.75510(16) 0.0578(6) Uani d . . . 1.0 . .
H H11 0.3819 0.6536 0.7937 0.069 Uiso calc U . R 1.0 . .
C C12 0.0296(2) 0.4492(2) 0.78306(19) 0.0760(8) Uani d . . D 1.0 . .
C C13A 0.0631(7) 0.4698(8) 0.8922(2) 0.124(3) Uani d U P D 0.531(7) A 1
H H13A 0.0109 0.4231 0.9188 0.186 Uiso calc U P R 0.531(7) A 1
H H13B 0.1509 0.452 0.922 0.186 Uiso calc U P R 0.531(7) A 1
H H13C 0.0484 0.5471 0.9039 0.186 Uiso calc U P R 0.531(7) A 1
C C14A 0.0633(8) 0.3252(2) 0.7740(7) 0.118(3) Uani d U P D 0.531(7) A 1
H H14A 0.0117 0.2786 0.8012 0.177 Uiso calc U P R 0.531(7) A 1
H H14B 0.0479 0.3066 0.7074 0.177 Uiso calc U P R 0.531(7) A 1
H H14C 0.1513 0.3131 0.8076 0.177 Uiso calc U P R 0.531(7) A 1
C C15A -0.1116(2) 0.4740(9) 0.7363(7) 0.139(4) Uani d U P D 0.531(7) A 1
H H15A -0.1617 0.4269 0.7646 0.209 Uiso calc U P R 0.531(7) A 1
H H15B -0.1285 0.5513 0.7465 0.209 Uiso calc U P R 0.531(7) A 1
H H15C -0.1332 0.4593 0.6686 0.209 Uiso calc U P R 0.531(7) A 1
C C13B 0.1107(6) 0.3780(9) 0.8661(7) 0.144(4) Uani d U P D 0.469(7) A 2
H H13D 0.0563 0.3328 0.8918 0.216 Uiso calc U P R 0.469(7) A 2
H H13E 0.1657 0.3303 0.8431 0.216 Uiso calc U P R 0.469(7) A 2
H H13F 0.161 0.4263 0.9155 0.216 Uiso calc U P R 0.469(7) A 2
C C14B -0.0512(8) 0.3679(7) 0.7069(5) 0.123(3) Uani d U P D 0.469(7) A 2
H H14D -0.1023 0.3223 0.7353 0.184 Uiso calc U P R 0.469(7) A 2
H H14E -0.1053 0.4101 0.6546 0.184 Uiso calc U P R 0.469(7) A 2
H H14F 0.0038 0.3207 0.6834 0.184 Uiso calc U P R 0.469(7) A 2
C C15B -0.0723(6) 0.5210(5) 0.8081(7) 0.101(3) Uani d U P D 0.469(7) A 2
H H15D -0.1236 0.4742 0.8354 0.152 Uiso calc U P R 0.469(7) A 2
H H15E -0.0318 0.5777 0.8537 0.152 Uiso calc U P R 0.469(7) A 2
H H15F -0.125 0.5561 0.7509 0.152 Uiso calc U P R 0.469(7) A 2
C C16 0.5712(2) 0.73074(18) 0.72487(17) 0.0531(5) Uani d . . . 1.0 . .
C C17 0.6223(2) 0.78206(19) 0.81907(16) 0.0558(5) Uani d . . . 1.0 . .
C C18 0.5434(2) 0.86800(18) 0.83148(16) 0.0542(5) Uani d . . . 1.0 . .
C C19 0.4263(2) 0.87808(19) 0.74796(17) 0.0569(5) Uani d . . . 1.0 . .
H H19A 0.4147 0.9546 0.7243 0.068 Uiso calc U . R 1.0 . .
H H19B 0.3517 0.8553 0.7657 0.068 Uiso calc U . R 1.0 . .
O O20 0.61174(17) 0.65271(15) 0.68980(14) 0.0733(5) Uani d . . . 1.0 . .
C C21 0.7333(3) 0.7555(3) 0.8909(2) 0.0789(8) Uani d . . . 1.0 . .
H H21 0.7858 0.6973 0.8833 0.095 Uiso calc U . R 1.0 . .
C C22 0.7624(3) 0.8190(3) 0.9739(2) 0.0978(11) Uani d . . . 1.0 . .
H H22 0.8358 0.8033 1.0234 0.117 Uiso calc U . R 1.0 . .
C C23 0.6843(4) 0.9052(3) 0.9845(2) 0.0928(10) Uani d . . . 1.0 . .
H H23 0.7068 0.9472 1.0408 0.111 Uiso calc U . R 1.0 . .
C C24 0.5759(3) 0.9303(2) 0.91522(19) 0.0720(7) Uani d . . . 1.0 . .
H H24 0.524 0.9885 0.9237 0.086 Uiso calc U . R 1.0 . .
O O25 0.4104(2) 0.97988(17) 0.56136(17) 0.0915(7) Uani d . . . 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N5 . 1.439(3) ?
O1 S2 . 1.638(2) ?
N5 C3 . 1.280(3) ?
C3 C6 . 1.475(3) ?
C3 C4 . 1.496(3) ?
C4 C19 . 1.534(3) ?
C4 C16 . 1.556(3) ?
C4 S2 . 1.855(2) ?
S2 O25 . 1.455(2) ?
C6 C7 . 1.386(3) ?
C6 C11 . 1.387(3) ?
C7 C8 . 1.376(4) ?
C7 H7 . 0.93 ?
C8 C9 . 1.393(4) ?
C8 H8 . 0.93 ?
C9 C10 . 1.391(3) ?
C9 C12 . 1.520(3) ?
C10 C11 . 1.375(3) ?
C10 H10 . 0.93 ?
C11 H11 . 0.93 ?
C12 C13B . 1.532(2) ?
C12 C15A . 1.533(2) ?
C12 C15B . 1.539(2) ?
C12 C14A . 1.539(2) ?
C12 C13A . 1.543(2) ?
C12 C14B . 1.544(2) ?
C13A H13A . 0.96 ?
C13A H13B . 0.96 ?
C13A H13C . 0.96 ?
C14A H14A . 0.96 ?
C14A H14B . 0.96 ?
C14A H14C . 0.96 ?
C15A H15A . 0.96 ?
C15A H15B . 0.96 ?
C15A H15C . 0.96 ?
C13B H13D . 0.96 ?
C13B H13E . 0.96 ?
C13B H13F . 0.96 ?
C14B H14D . 0.96 ?
C14B H14E . 0.96 ?
C14B H14F . 0.96 ?
C15B H15D . 0.96 ?
C15B H15E . 0.96 ?
C15B H15F . 0.96 ?
C16 O20 . 1.208(3) ?
C16 C17 . 1.456(3) ?
C17 C18 . 1.390(3) ?
C17 C21 . 1.392(3) ?
C18 C24 . 1.382(3) ?
C18 C19 . 1.495(3) ?
C19 H19A . 0.97 ?
C19 H19B . 0.97 ?
C21 C22 . 1.383(5) ?
C21 H21 . 0.93 ?
C22 C23 . 1.377(5) ?
C22 H22 . 0.93 ?
C23 C24 . 1.351(5) ?
C23 H23 . 0.93 ?
C24 H24 . 0.93 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N5 O1 S2 . . 115.03(14) ?
C3 N5 O1 . . 110.2(2) ?
N5 C3 C6 . . 118.9(2) ?
N5 C3 C4 . . 117.8(2) ?
C6 C3 C4 . . 123.19(18) ?
C3 C4 C19 . . 119.49(18) ?
C3 C4 C16 . . 112.30(18) ?
C19 C4 C16 . . 105.66(17) ?
C3 C4 S2 . . 101.98(14) ?
C19 C4 S2 . . 110.23(15) ?
C16 C4 S2 . . 106.57(14) ?
O25 S2 O1 . . 108.34(13) ?
O25 S2 C4 . . 106.04(11) ?
O1 S2 C4 . . 90.01(9) ?
C7 C6 C11 . . 117.7(2) ?
C7 C6 C3 . . 120.8(2) ?
C11 C6 C3 . . 121.4(2) ?
C8 C7 C6 . . 120.9(2) ?
C8 C7 H7 . . 119.5 ?
C6 C7 H7 . . 119.5 ?
C7 C8 C9 . . 121.9(2) ?
C7 C8 H8 . . 119.0 ?
C9 C8 H8 . . 119.0 ?
C10 C9 C8 . . 116.5(2) ?
C10 C9 C12 . . 121.9(2) ?
C8 C9 C12 . . 121.6(2) ?
C11 C10 C9 . . 121.8(2) ?
C11 C10 H10 . . 119.1 ?
C9 C10 H10 . . 119.1 ?
C10 C11 C6 . . 121.1(2) ?
C10 C11 H11 . . 119.4 ?
C6 C11 H11 . . 119.4 ?
C9 C12 C13B . . 111.5(3) ?
C9 C12 C15A . . 110.7(3) ?
C9 C12 C15B . . 110.0(2) ?
C13B C12 C15B . . 114.7(5) ?
C9 C12 C14A . . 109.2(2) ?
C15A C12 C14A . . 112.7(5) ?
C9 C12 C13A . . 110.2(2) ?
C15A C12 C13A . . 109.3(5) ?
C14A C12 C13A . . 104.5(5) ?
C9 C12 C14B . . 110.5(3) ?
C13B C12 C14B . . 107.4(5) ?
C15B C12 C14B . . 102.3(5) ?
C12 C13A H13A . . 109.5 ?
C12 C13A H13B . . 109.5 ?
H13A C13A H13B . . 109.5 ?
C12 C13A H13C . . 109.5 ?
H13A C13A H13C . . 109.5 ?
H13B C13A H13C . . 109.5 ?
C12 C14A H14A . . 109.5 ?
C12 C14A H14B . . 109.5 ?
H14A C14A H14B . . 109.5 ?
C12 C14A H14C . . 109.5 ?
H14A C14A H14C . . 109.5 ?
H14B C14A H14C . . 109.5 ?
C12 C15A H15A . . 109.5 ?
C12 C15A H15B . . 109.5 ?
H15A C15A H15B . . 109.5 ?
C12 C15A H15C . . 109.5 ?
H15A C15A H15C . . 109.5 ?
H15B C15A H15C . . 109.5 ?
C12 C13B H13D . . 109.5 ?
C12 C13B H13E . . 109.5 ?
H13D C13B H13E . . 109.5 ?
C12 C13B H13F . . 109.5 ?
H13D C13B H13F . . 109.5 ?
H13E C13B H13F . . 109.5 ?
C12 C14B H14D . . 109.5 ?
C12 C14B H14E . . 109.5 ?
H14D C14B H14E . . 109.5 ?
C12 C14B H14F . . 109.5 ?
H14D C14B H14F . . 109.5 ?
H14E C14B H14F . . 109.5 ?
C12 C15B H15D . . 109.5 ?
C12 C15B H15E . . 109.5 ?
H15D C15B H15E . . 109.5 ?
C12 C15B H15F . . 109.5 ?
H15D C15B H15F . . 109.5 ?
H15E C15B H15F . . 109.5 ?
O20 C16 C17 . . 129.3(2) ?
O20 C16 C4 . . 124.2(2) ?
C17 C16 C4 . . 106.45(18) ?
C18 C17 C21 . . 121.0(2) ?
C18 C17 C16 . . 110.4(2) ?
C21 C17 C16 . . 128.6(2) ?
C24 C18 C17 . . 120.1(2) ?
C24 C18 C19 . . 127.8(2) ?
C17 C18 C19 . . 112.1(2) ?
C18 C19 C4 . . 104.29(18) ?
C18 C19 H19A . . 110.9 ?
C4 C19 H19A . . 110.9 ?
C18 C19 H19B . . 110.9 ?
C4 C19 H19B . . 110.9 ?
H19A C19 H19B . . 108.9 ?
C22 C21 C17 . . 117.4(3) ?
C22 C21 H21 . . 121.3 ?
C17 C21 H21 . . 121.3 ?
C23 C22 C21 . . 121.0(3) ?
C23 C22 H22 . . 119.5 ?
C21 C22 H22 . . 119.5 ?
C24 C23 C22 . . 121.7(3) ?
C24 C23 H23 . . 119.2 ?
C22 C23 H23 . . 119.2 ?
C23 C24 C18 . . 118.9(3) ?
C23 C24 H24 . . 120.6 ?
C18 C24 H24 . . 120.6 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
S2 O1 N5 C3 . . . . -15.2(3) ?
O1 N5 C3 C6 . . . . -178.68(18) ?
O1 N5 C3 C4 . . . . -2.0(3) ?
N5 C3 C4 C19 . . . . 137.0(2) ?
C6 C3 C4 C19 . . . . -46.5(3) ?
N5 C3 C4 C16 . . . . -98.5(2) ?
C6 C3 C4 C16 . . . . 78.0(2) ?
N5 C3 C4 S2 . . . . 15.2(2) ?
C6 C3 C4 S2 . . . . -168.26(17) ?
N5 O1 S2 O25 . . . . -86.37(18) ?
N5 O1 S2 C4 . . . . 20.56(17) ?
C3 C4 S2 O25 . . . . 90.13(17) ?
C19 C4 S2 O25 . . . . -37.79(19) ?
C16 C4 S2 O25 . . . . -151.98(17) ?
C3 C4 S2 O1 . . . . -18.98(15) ?
C19 C4 S2 O1 . . . . -146.90(16) ?
C16 C4 S2 O1 . . . . 98.91(15) ?
N5 C3 C6 C7 . . . . -23.8(3) ?
C4 C3 C6 C7 . . . . 159.7(2) ?
N5 C3 C6 C11 . . . . 153.9(2) ?
C4 C3 C6 C11 . . . . -22.5(3) ?
C11 C6 C7 C8 . . . . -0.9(4) ?
C3 C6 C7 C8 . . . . 176.9(2) ?
C6 C7 C8 C9 . . . . 0.7(4) ?
C7 C8 C9 C10 . . . . -0.2(4) ?
C7 C8 C9 C12 . . . . 179.7(2) ?
C8 C9 C10 C11 . . . . -0.1(4) ?
C12 C9 C10 C11 . . . . 180.0(2) ?
C9 C10 C11 C6 . . . . -0.2(4) ?
C7 C6 C11 C10 . . . . 0.7(4) ?
C3 C6 C11 C10 . . . . -177.2(2) ?
C10 C9 C12 C13B . . . . -29.8(6) ?
C8 C9 C12 C13B . . . . 150.2(6) ?
C10 C9 C12 C15A . . . . 145.8(5) ?
C8 C9 C12 C15A . . . . -34.2(6) ?
C10 C9 C12 C15B . . . . 98.5(5) ?
C8 C9 C12 C15B . . . . -81.4(5) ?
C10 C9 C12 C14A . . . . -89.6(5) ?
C8 C9 C12 C14A . . . . 90.5(5) ?
C10 C9 C12 C13A . . . . 24.7(5) ?
C8 C9 C12 C13A . . . . -155.2(5) ?
C10 C9 C12 C14B . . . . -149.2(5) ?
C8 C9 C12 C14B . . . . 30.9(5) ?
C3 C4 C16 O20 . . . . 41.0(3) ?
C19 C4 C16 O20 . . . . 172.9(2) ?
S2 C4 C16 O20 . . . . -69.9(2) ?
C3 C4 C16 C17 . . . . -140.42(19) ?
C19 C4 C16 C17 . . . . -8.5(2) ?
S2 C4 C16 C17 . . . . 108.72(17) ?
O20 C16 C17 C18 . . . . -178.2(2) ?
C4 C16 C17 C18 . . . . 3.4(2) ?
O20 C16 C17 C21 . . . . 2.2(4) ?
C4 C16 C17 C21 . . . . -176.3(2) ?
C21 C17 C18 C24 . . . . 1.5(3) ?
C16 C17 C18 C24 . . . . -178.2(2) ?
C21 C17 C18 C19 . . . . -176.8(2) ?
C16 C17 C18 C19 . . . . 3.5(3) ?
C24 C18 C19 C4 . . . . 173.1(2) ?
C17 C18 C19 C4 . . . . -8.8(2) ?
C3 C4 C19 C18 . . . . 137.84(19) ?
C16 C4 C19 C18 . . . . 10.2(2) ?
S2 C4 C19 C18 . . . . -104.61(17) ?
C18 C17 C21 C22 . . . . -1.0(4) ?
C16 C17 C21 C22 . . . . 178.6(3) ?
C17 C21 C22 C23 . . . . -0.1(5) ?
C21 C22 C23 C24 . . . . 0.8(5) ?
C22 C23 C24 C18 . . . . -0.4(5) ?
C17 C18 C24 C23 . . . . -0.7(4) ?
C19 C18 C24 C23 . . . . 177.3(3) ?



####################################################################### 
# 
# 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_I_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1875542'
_audit_update_record             
;
2018-10-26 deposited with the CCDC.
2018-12-12 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C16 H9 F2 N O2 S'
_chemical_formula_sum            'C16 H9 F2 N O2 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         317.30

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   14.0083(10)
_cell_length_b                   8.7108(6)
_cell_length_c                   11.5419(8)
_cell_angle_alpha                90
_cell_angle_beta                 105.733(2)
_cell_angle_gamma                90
_cell_volume                     1355.62(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2755
_cell_measurement_theta_min      3.28
_cell_measurement_theta_max      67.13
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.521
_exptl_crystal_size_mid          0.395
_exptl_crystal_size_min          0.293
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648

_exptl_absorpt_coefficient_mu    2.417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.6190
_exptl_absorpt_correction_T_max  00.7529

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   'Incoatec Microfocus X-ray Source I\mS'
_diffrn_source_type              microfocus

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Incoatec Montel Multilayer Mirror'

_diffrn_measurement_device_type  'Bruker AXS Kappa APEX II DUO'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            15370
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_theta_min         3.28
_diffrn_reflns_theta_max         67.13
_diffrn_reflns_theta_full        67.13
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       6

_refine_special_details          
;
;

_reflns_number_total             2344
_reflns_number_gt                2299
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0927
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_refine_ls_number_reflns         2344
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0506P)²+0.3012P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.205
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?


loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.21938(8) 0.84113(14) 0.27877(12) 0.0608(3) Uani d . . . 1 . .
N N2 0.31365(9) 0.82273(16) 0.35939(12) 0.0491(3) Uani d . . . 1 . .
C C3 0.36485(10) 0.72042(16) 0.32377(12) 0.0401(3) Uani d . . . 1 . .
S S4 0.30739(3) 0.62456(5) 0.18984(3) 0.05135(16) Uani d . . . 1 . .
C C5 0.19324(11) 0.72470(18) 0.18534(13) 0.0461(4) Uani d . . . 1 . .
C C6 0.46783(10) 0.69062(16) 0.39360(12) 0.0398(3) Uani d . . . 1 . .
C C7 0.52710(11) 0.58220(18) 0.36016(14) 0.0468(3) Uani d . . . 1 . .
C C8 0.62275(12) 0.5513(2) 0.42701(16) 0.0567(4) Uani d . . . 1 . .
H H8 0.6602 0.4773 0.4012 0.068 Uiso calc U . R 1 . .
C C9 0.66204(12) 0.6301(2) 0.53146(16) 0.0561(4) Uani d . . . 1 . .
H H9 0.7262 0.6106 0.5782 0.067 Uiso calc U . R 1 . .
C C10 0.60405(12) 0.7390(2) 0.56525(14) 0.0537(4) Uani d . . . 1 . .
C C11 0.50915(12) 0.77203(18) 0.49990(14) 0.0495(4) Uani d . . . 1 . .
H H11 0.4727 0.8475 0.5258 0.059 Uiso calc U . R 1 . .
F F12 0.49066(7) 0.49952(13) 0.25855(10) 0.0689(3) Uani d . . . 1 . .
F F13 0.64282(9) 0.81626(17) 0.66934(10) 0.0849(4) Uani d . . . 1 . .
C C14 0.11414(11) 0.62005(18) 0.21701(13) 0.0451(3) Uani d . . . 1 . .
C C15 0.02086(11) 0.64572(17) 0.12530(13) 0.0421(3) Uani d . . . 1 . .
C C16 0.03522(11) 0.74726(18) 0.03909(13) 0.0455(3) Uani d . . . 1 . .
C C17 0.14160(12) 0.7977(2) 0.06469(15) 0.0549(4) Uani d . . . 1 . .
H H17A 0.1466 0.9087 0.0695 0.066 Uiso calc U . R 1 . .
H H17B 0.1707 0.7621 0.0023 0.066 Uiso calc U . R 1 . .
O O18 0.13011(9) 0.53861(16) 0.30499(11) 0.0660(3) Uani d . . . 1 . .
C C19 -0.07165(12) 0.5816(2) 0.11833(15) 0.0520(4) Uani d . . . 1 . .
H H19 -0.08 0.5131 0.1766 0.062 Uiso calc U . R 1 . .
C C20 -0.14971(12) 0.6220(2) 0.02359(17) 0.0614(5) Uani d . . . 1 . .
H H20 -0.2125 0.5822 0.0177 0.074 Uiso calc U . R 1 . .
C C21 -0.13574(13) 0.7224(2) -0.06390(17) 0.0677(5) Uani d . . . 1 . .
H H21 -0.1894 0.7474 -0.1285 0.081 Uiso calc U . R 1 . .
C C22 -0.04414(13) 0.7857(2) -0.05734(15) 0.0596(4) Uani d . . . 1 . .
H H22 -0.0359 0.8529 -0.1165 0.072 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N2 . 1.4032(17) ?
O1 C5 . 1.4530(19) ?
N2 C3 . 1.2796(19) ?
C3 C6 . 1.472(2) ?
C3 S4 . 1.7492(14) ?
S4 C5 . 1.8099(15) ?
C5 C17 . 1.523(2) ?
C5 C14 . 1.553(2) ?
C6 C7 . 1.380(2) ?
C6 C11 . 1.399(2) ?
C7 F12 . 1.3528(19) ?
C7 C8 . 1.379(2) ?
C8 C9 . 1.367(3) ?
C8 H8 . 0.93 ?
C9 C10 . 1.372(3) ?
C9 H9 . 0.93 ?
C10 F13 . 1.3553(19) ?
C10 C11 . 1.369(2) ?
C11 H11 . 0.93 ?
C14 O18 . 1.2088(19) ?
C14 C15 . 1.459(2) ?
C15 C16 . 1.386(2) ?
C15 C19 . 1.393(2) ?
C16 C22 . 1.384(2) ?
C16 C17 . 1.504(2) ?
C17 H17A . 0.97 ?
C17 H17B . 0.97 ?
C19 C20 . 1.366(3) ?
C19 H19 . 0.93 ?
C20 C21 . 1.389(3) ?
C20 H20 . 0.93 ?
C21 C22 . 1.380(3) ?
C21 H21 . 0.93 ?
C22 H22 . 0.93 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 O1 C5 . . 114.52(11) ?
C3 N2 O1 . . 112.03(12) ?
N2 C3 C6 . . 119.89(13) ?
N2 C3 S4 . . 116.92(11) ?
C6 C3 S4 . . 123.18(10) ?
C3 S4 C5 . . 89.23(7) ?
O1 C5 C17 . . 110.41(13) ?
O1 C5 C14 . . 106.70(12) ?
C17 C5 C14 . . 105.54(12) ?
O1 C5 S4 . . 105.79(9) ?
C17 C5 S4 . . 115.10(11) ?
C14 C5 S4 . . 113.05(11) ?
C7 C6 C11 . . 117.06(14) ?
C7 C6 C3 . . 122.83(13) ?
C11 C6 C3 . . 120.10(13) ?
F12 C7 C8 . . 117.52(14) ?
F12 C7 C6 . . 119.51(13) ?
C8 C7 C6 . . 122.96(15) ?
C9 C8 C7 . . 119.54(16) ?
C9 C8 H8 . . 120.2 ?
C7 C8 H8 . . 120.2 ?
C8 C9 C10 . . 118.05(15) ?
C8 C9 H9 . . 121.0 ?
C10 C9 H9 . . 121.0 ?
F13 C10 C11 . . 118.68(16) ?
F13 C10 C9 . . 117.98(15) ?
C11 C10 C9 . . 123.34(16) ?
C10 C11 C6 . . 119.05(15) ?
C10 C11 H11 . . 120.5 ?
C6 C11 H11 . . 120.5 ?
O18 C14 C15 . . 128.67(15) ?
O18 C14 C5 . . 124.12(14) ?
C15 C14 C5 . . 107.17(12) ?
C16 C15 C19 . . 121.87(15) ?
C16 C15 C14 . . 110.06(13) ?
C19 C15 C14 . . 128.07(14) ?
C22 C16 C15 . . 119.37(15) ?
C22 C16 C17 . . 128.63(15) ?
C15 C16 C17 . . 111.97(13) ?
C16 C17 C5 . . 104.91(12) ?
C16 C17 H17A . . 110.8 ?
C5 C17 H17A . . 110.8 ?
C16 C17 H17B . . 110.8 ?
C5 C17 H17B . . 110.8 ?
H17A C17 H17B . . 108.8 ?
C20 C19 C15 . . 118.21(17) ?
C20 C19 H19 . . 120.9 ?
C15 C19 H19 . . 120.9 ?
C19 C20 C21 . . 120.28(17) ?
C19 C20 H20 . . 119.9 ?
C21 C20 H20 . . 119.9 ?
C22 C21 C20 . . 121.60(16) ?
C22 C21 H21 . . 119.2 ?
C20 C21 H21 . . 119.2 ?
C21 C22 C16 . . 118.65(17) ?
C21 C22 H22 . . 120.7 ?
C16 C22 H22 . . 120.7 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 O1 N2 C3 . . . . 10.33(19) ?
O1 N2 C3 C6 . . . . 176.85(12) ?
O1 N2 C3 S4 . . . . -1.90(18) ?
N2 C3 S4 C5 . . . . -5.05(13) ?
C6 C3 S4 C5 . . . . 176.25(12) ?
N2 O1 C5 C17 . . . . -138.37(13) ?
N2 O1 C5 C14 . . . . 107.42(14) ?
N2 O1 C5 S4 . . . . -13.22(16) ?
C3 S4 C5 O1 . . . . 9.73(11) ?
C3 S4 C5 C17 . . . . 131.93(13) ?
C3 S4 C5 C14 . . . . -106.69(11) ?
N2 C3 C6 C7 . . . . -179.90(14) ?
S4 C3 C6 C7 . . . . -1.2(2) ?
N2 C3 C6 C11 . . . . 1.2(2) ?
S4 C3 C6 C11 . . . . 179.82(11) ?
C11 C6 C7 F12 . . . . 179.59(13) ?
C3 C6 C7 F12 . . . . 0.6(2) ?
C11 C6 C7 C8 . . . . 0.7(2) ?
C3 C6 C7 C8 . . . . -178.29(14) ?
F12 C7 C8 C9 . . . . -178.86(15) ?
C6 C7 C8 C9 . . . . 0.1(3) ?
C7 C8 C9 C10 . . . . -0.5(2) ?
C8 C9 C10 F13 . . . . 179.47(15) ?
C8 C9 C10 C11 . . . . 0.2(3) ?
F13 C10 C11 C6 . . . . -178.70(14) ?
C9 C10 C11 C6 . . . . 0.6(2) ?
C7 C6 C11 C10 . . . . -1.0(2) ?
C3 C6 C11 C10 . . . . 178.02(13) ?
O1 C5 C14 O18 . . . . -65.64(19) ?
C17 C5 C14 O18 . . . . 176.88(16) ?
S4 C5 C14 O18 . . . . 50.23(19) ?
O1 C5 C14 C15 . . . . 111.99(13) ?
C17 C5 C14 C15 . . . . -5.49(16) ?
S4 C5 C14 C15 . . . . -132.14(11) ?
O18 C14 C15 C16 . . . . -179.58(16) ?
C5 C14 C15 C16 . . . . 2.93(16) ?
O18 C14 C15 C19 . . . . 0.0(3) ?
C5 C14 C15 C19 . . . . -177.52(14) ?
C19 C15 C16 C22 . . . . -0.5(2) ?
C14 C15 C16 C22 . . . . 179.13(14) ?
C19 C15 C16 C17 . . . . -178.66(14) ?
C14 C15 C16 C17 . . . . 0.93(18) ?
C22 C16 C17 C5 . . . . 177.60(16) ?
C15 C16 C17 C5 . . . . -4.41(18) ?
O1 C5 C17 C16 . . . . -109.13(14) ?
C14 C5 C17 C16 . . . . 5.82(16) ?
S4 C5 C17 C16 . . . . 131.20(12) ?
C16 C15 C19 C20 . . . . -0.4(2) ?
C14 C15 C19 C20 . . . . -179.93(14) ?
C15 C19 C20 C21 . . . . 1.1(2) ?
C19 C20 C21 C22 . . . . -1.0(3) ?
C20 C21 C22 C16 . . . . 0.1(3) ?
C15 C16 C22 C21 . . . . 0.6(2) ?
C17 C16 C22 C21 . . . . 178.47(16) ?



####################################################################### 
# 
# 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_I_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1875543'
_audit_update_record             
;
2018-10-26 deposited with the CCDC.
2018-12-12 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C17 H12 F N O3 S'
_chemical_formula_sum            'C17 H12 F N O3 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         329.34

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
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                   15.237(3)
_cell_length_b                   11.212(2)
_cell_length_c                   17.948(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3066.2(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9840
_cell_measurement_theta_min      2.9001
_cell_measurement_theta_max      67.1151
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.498
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.191
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360

_exptl_absorpt_coefficient_mu    2.111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.44
_exptl_absorpt_correction_T_max  0.75

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   'Incoatec Microfocus X-ray Source I\mS'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Incoatec Montel Multilayer Mirror'

_diffrn_measurement_device_type  'Bruker ACS Kappa APEX II DUO diffractometer'
_diffrn_measurement_method       'ω and φ scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            16848
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_theta_min         5.72
_diffrn_reflns_theta_max         67.14
_diffrn_reflns_theta_full        67.14
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measured_fraction_theta_full 0.958
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       11

_refine_special_details          
;
;

_reflns_number_total             2637
_reflns_number_gt                2617
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_gt          0.1302
_refine_ls_wR_factor_ref         0.1303
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_refine_ls_number_reflns         2637
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0709P)²+1.4891P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.300
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.61190(10) 0.19193(16) 0.12733(10) 0.0583(5) Uani d . . . 1 . .
N N5 0.55175(11) 0.28150(17) 0.10054(10) 0.0465(4) Uani d . . . 1 . .
C C3 0.49574(12) 0.30703(16) 0.15108(10) 0.0330(4) Uani d . . . 1 . .
C C4 0.50031(12) 0.24053(16) 0.22371(10) 0.0329(4) Uani d . . . 1 . .
S S2 0.61234(3) 0.17485(5) 0.21852(3) 0.0461(2) Uani d . . . 1 . .
C C6 0.42913(11) 0.39879(15) 0.13479(9) 0.0314(4) Uani d . . . 1 . .
C C7 0.45132(13) 0.49762(17) 0.09121(10) 0.0372(4) Uani d . . . 1 . .
H H7 0.5085 0.5059 0.0739 0.045 Uiso calc U . R 1 . .
C C8 0.38979(14) 0.58280(19) 0.07353(11) 0.0446(5) Uani d . . . 1 . .
H H8 0.4044 0.6484 0.0443 0.054 Uiso calc U . R 1 . .
C C9 0.30584(15) 0.56781(18) 0.10043(11) 0.0446(5) Uani d . . . 1 . .
C C10 0.28092(13) 0.47222(19) 0.14302(11) 0.0431(5) Uani d . . . 1 . .
H H10 0.2233 0.4645 0.1595 0.052 Uiso calc U . R 1 . .
C C11 0.34324(12) 0.38754(17) 0.16096(10) 0.0369(4) Uani d . . . 1 . .
H H11 0.3279 0.3227 0.1906 0.044 Uiso calc U . R 1 . .
F F12 0.24522(10) 0.65212(14) 0.08347(9) 0.0729(5) Uani d . . . 1 . .
C C13 0.43539(12) 0.13258(16) 0.22611(10) 0.0346(4) Uani d . . . 1 . .
C C14 0.39400(12) 0.13485(18) 0.29978(11) 0.0378(4) Uani d . . . 1 . .
C C15 0.33558(14) 0.0520(2) 0.32975(13) 0.0483(5) Uani d . . . 1 . .
H H15 0.3172 -0.0141 0.3027 0.058 Uiso calc U . R 1 . .
C C16 0.30635(16) 0.0724(2) 0.40123(14) 0.0581(6) Uani d . . . 1 . .
H H16 0.2676 0.0189 0.4232 0.07 Uiso calc U . R 1 . .
C C17 0.33410(16) 0.1721(2) 0.44110(14) 0.0588(7) Uani d . . . 1 . .
H H17 0.3129 0.1831 0.4892 0.071 Uiso calc U . R 1 . .
C C18 0.39199(15) 0.2558(2) 0.41221(12) 0.0484(5) Uani d . . . 1 . .
C C19 0.42190(13) 0.23428(17) 0.33978(10) 0.0376(4) Uani d . . . 1 . .
C C20 0.48534(14) 0.30999(17) 0.29596(11) 0.0392(5) Uani d . . . 1 . .
H H20A 0.54 0.3202 0.323 0.047 Uiso calc U . R 1 . .
H H20B 0.4605 0.3879 0.2857 0.047 Uiso calc U . R 1 . .
O O21 0.42561(10) 0.06335(12) 0.17530(8) 0.0472(4) Uani d . . . 1 . .
C C22 0.4231(2) 0.3633(3) 0.45553(14) 0.0666(7) Uani d . . . 1 . .
H H22A 0.3887 0.3716 0.5 0.1 Uiso calc U . R 1 . .
H H22B 0.4168 0.4335 0.4254 0.1 Uiso calc U . R 1 . .
H H22C 0.4837 0.353 0.4687 0.1 Uiso calc U . R 1 . .
O O23 0.67174(10) 0.26123(15) 0.25165(11) 0.0616(5) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N5 . 1.442(2) ?
O1 S2 . 1.6479(19) ?
N5 C3 . 1.278(3) ?
C3 C6 . 1.474(2) ?
C3 C4 . 1.503(2) ?
C4 C20 . 1.530(3) ?
C4 C13 . 1.564(2) ?
C4 S2 . 1.8614(19) ?
S2 O23 . 1.4527(17) ?
C6 C11 . 1.396(3) ?
C6 C7 . 1.398(2) ?
C7 C8 . 1.375(3) ?
C7 H7 . 0.93 ?
C8 C9 . 1.378(3) ?
C8 H8 . 0.93 ?
C9 F12 . 1.356(2) ?
C9 C10 . 1.370(3) ?
C10 C11 . 1.381(3) ?
C10 H10 . 0.93 ?
C11 H11 . 0.93 ?
C13 O21 . 1.207(2) ?
C13 C14 . 1.465(3) ?
C14 C19 . 1.392(3) ?
C14 C15 . 1.394(3) ?
C15 C16 . 1.377(4) ?
C15 H15 . 0.93 ?
C16 C17 . 1.393(4) ?
C16 H16 . 0.93 ?
C17 C18 . 1.388(4) ?
C17 H17 . 0.93 ?
C18 C19 . 1.399(3) ?
C18 C22 . 1.511(4) ?
C19 C20 . 1.508(3) ?
C20 H20A . 0.97 ?
C20 H20B . 0.97 ?
C22 H22A . 0.96 ?
C22 H22B . 0.96 ?
C22 H22C . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N5 O1 S2 . . 114.49(12) ?
C3 N5 O1 . . 110.11(16) ?
N5 C3 C6 . . 118.38(17) ?
N5 C3 C4 . . 118.26(17) ?
C6 C3 C4 . . 123.36(15) ?
C3 C4 C20 . . 118.40(15) ?
C3 C4 C13 . . 112.23(14) ?
C20 C4 C13 . . 106.04(15) ?
C3 C4 S2 . . 101.27(12) ?
C20 C4 S2 . . 112.37(13) ?
C13 C4 S2 . . 105.98(12) ?
O23 S2 O1 . . 109.36(11) ?
O23 S2 C4 . . 106.69(9) ?
O1 S2 C4 . . 90.00(8) ?
C11 C6 C7 . . 119.12(17) ?
C11 C6 C3 . . 121.04(16) ?
C7 C6 C3 . . 119.83(16) ?
C8 C7 C6 . . 120.97(18) ?
C8 C7 H7 . . 119.5 ?
C6 C7 H7 . . 119.5 ?
C7 C8 C9 . . 117.86(18) ?
C7 C8 H8 . . 121.1 ?
C9 C8 H8 . . 121.1 ?
F12 C9 C10 . . 118.8(2) ?
F12 C9 C8 . . 117.95(19) ?
C10 C9 C8 . . 123.25(19) ?
C9 C10 C11 . . 118.51(18) ?
C9 C10 H10 . . 120.7 ?
C11 C10 H10 . . 120.7 ?
C10 C11 C6 . . 120.27(17) ?
C10 C11 H11 . . 119.9 ?
C6 C11 H11 . . 119.9 ?
O21 C13 C14 . . 129.79(18) ?
O21 C13 C4 . . 123.72(17) ?
C14 C13 C4 . . 106.48(15) ?
C19 C14 C15 . . 122.0(2) ?
C19 C14 C13 . . 110.36(17) ?
C15 C14 C13 . . 127.7(2) ?
C16 C15 C14 . . 117.1(2) ?
C16 C15 H15 . . 121.5 ?
C14 C15 H15 . . 121.5 ?
C15 C16 C17 . . 120.9(2) ?
C15 C16 H16 . . 119.5 ?
C17 C16 H16 . . 119.5 ?
C18 C17 C16 . . 122.9(2) ?
C18 C17 H17 . . 118.5 ?
C16 C17 H17 . . 118.5 ?
C17 C18 C19 . . 116.0(2) ?
C17 C18 C22 . . 123.1(2) ?
C19 C18 C22 . . 120.9(2) ?
C14 C19 C18 . . 121.18(19) ?
C14 C19 C20 . . 112.18(17) ?
C18 C19 C20 . . 126.64(19) ?
C19 C20 C4 . . 104.54(15) ?
C19 C20 H20A . . 110.8 ?
C4 C20 H20A . . 110.8 ?
C19 C20 H20B . . 110.8 ?
C4 C20 H20B . . 110.8 ?
H20A C20 H20B . . 108.9 ?
C18 C22 H22A . . 109.5 ?
C18 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C18 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
S2 O1 N5 C3 . . . . -16.6(2) ?
O1 N5 C3 C6 . . . . 178.99(15) ?
O1 N5 C3 C4 . . . . -1.9(2) ?
N5 C3 C4 C20 . . . . 139.61(19) ?
C6 C3 C4 C20 . . . . -41.4(2) ?
N5 C3 C4 C13 . . . . -96.3(2) ?
C6 C3 C4 C13 . . . . 82.7(2) ?
N5 C3 C4 S2 . . . . 16.3(2) ?
C6 C3 C4 S2 . . . . -164.66(14) ?
N5 O1 S2 O23 . . . . -85.38(15) ?
N5 O1 S2 C4 . . . . 22.34(15) ?
C3 C4 S2 O23 . . . . 89.82(14) ?
C20 C4 S2 O23 . . . . -37.51(16) ?
C13 C4 S2 O23 . . . . -152.90(13) ?
C3 C4 S2 O1 . . . . -20.43(13) ?
C20 C4 S2 O1 . . . . -147.76(14) ?
C13 C4 S2 O1 . . . . 96.85(13) ?
N5 C3 C6 C11 . . . . 142.68(19) ?
C4 C3 C6 C11 . . . . -36.3(3) ?
N5 C3 C6 C7 . . . . -36.0(3) ?
C4 C3 C6 C7 . . . . 145.01(17) ?
C11 C6 C7 C8 . . . . -0.5(3) ?
C3 C6 C7 C8 . . . . 178.22(17) ?
C6 C7 C8 C9 . . . . 0.3(3) ?
C7 C8 C9 F12 . . . . 179.57(18) ?
C7 C8 C9 C10 . . . . -0.6(3) ?
F12 C9 C10 C11 . . . . -179.12(18) ?
C8 C9 C10 C11 . . . . 1.1(3) ?
C9 C10 C11 C6 . . . . -1.2(3) ?
C7 C6 C11 C10 . . . . 0.9(3) ?
C3 C6 C11 C10 . . . . -177.75(17) ?
C3 C4 C13 O21 . . . . 44.2(2) ?
C20 C4 C13 O21 . . . . 174.90(18) ?
S2 C4 C13 O21 . . . . -65.5(2) ?
C3 C4 C13 C14 . . . . -136.76(16) ?
C20 C4 C13 C14 . . . . -6.05(18) ?
S2 C4 C13 C14 . . . . 113.57(13) ?
O21 C13 C14 C19 . . . . -177.41(19) ?
C4 C13 C14 C19 . . . . 3.6(2) ?
O21 C13 C14 C15 . . . . 3.4(3) ?
C4 C13 C14 C15 . . . . -175.55(18) ?
C19 C14 C15 C16 . . . . -0.1(3) ?
C13 C14 C15 C16 . . . . 178.96(19) ?
C14 C15 C16 C17 . . . . 0.3(3) ?
C15 C16 C17 C18 . . . . -0.2(4) ?
C16 C17 C18 C19 . . . . -0.2(3) ?
C16 C17 C18 C22 . . . . -179.2(2) ?
C15 C14 C19 C18 . . . . -0.3(3) ?
C13 C14 C19 C18 . . . . -179.50(17) ?
C15 C14 C19 C20 . . . . 179.56(18) ?
C13 C14 C19 C20 . . . . 0.3(2) ?
C17 C18 C19 C14 . . . . 0.4(3) ?
C22 C18 C19 C14 . . . . 179.5(2) ?
C17 C18 C19 C20 . . . . -179.37(19) ?
C22 C18 C19 C20 . . . . -0.3(3) ?
C14 C19 C20 C4 . . . . -4.2(2) ?
C18 C19 C20 C4 . . . . 175.63(18) ?
C3 C4 C20 C19 . . . . 133.15(16) ?
C13 C4 C20 C19 . . . . 6.06(19) ?
S2 C4 C20 C19 . . . . -109.29(15) ?



####################################################################### 
# 
# 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_I_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1875540'
_audit_update_record             
;
2018-10-26 deposited with the CCDC.
2018-12-12 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C16 H11 N O3 S'
_chemical_formula_sum            'C16 H11 N O3 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         297.32

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.342(2)
_cell_length_b                   8.954(3)
_cell_length_c                   11.714(3)
_cell_angle_alpha                70.226(9)
_cell_angle_beta                 83.607(9)
_cell_angle_gamma                72.230(9)
_cell_volume                     690.1(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3237
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      25.05
_cell_measurement_temperature    300.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.400
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             308

_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
'SADABS V2014/4 (Bruker AXS Inc.)'
;
_exptl_absorpt_correction_T_min  0.7006
_exptl_absorpt_correction_T_max  1.0000

_exptl_special_details           
;
;

_diffrn_ambient_temperature      300.(2)

_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'Bruker X2S'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'doubly curved silicon crystal'

_diffrn_measurement_device_type  'Bruker SMART X2S'
_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean 8.33333

_diffrn_reflns_number            6640
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_theta_min         2.91
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
;

_reflns_number_total             2407
_reflns_number_gt                1976
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1166
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_number_reflns         2407
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0576P)²+0.1657P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.301
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 1.1012(3) 0.9816(2) 0.23454(16) 0.0785(5) Uani d . . . 1 . .
N N5 0.9727(3) 0.9621(2) 0.33808(18) 0.0662(5) Uani d . . . 1 . .
C C3 0.8991(3) 0.8456(2) 0.34865(17) 0.0465(5) Uani d . . . 1 . .
C C4 0.9499(3) 0.7621(2) 0.25327(16) 0.0447(4) Uani d . . . 1 . .
S S2 1.16608(9) 0.82459(8) 0.18166(5) 0.0658(2) Uani d . . . 1 . .
O O6 1.3300(2) 0.6997(2) 0.2485(2) 0.0905(6) Uani d . . . 1 . .
C C7 0.7619(3) 0.8079(2) 0.44785(17) 0.0464(4) Uani d . . . 1 . .
C C8 0.6230(3) 0.7349(3) 0.4392(2) 0.0566(5) Uani d . . . 1 . .
H H8 0.6194 0.705 0.3709 0.068 Uiso calc U . R 1 . .
C C9 0.4914(3) 0.7071(3) 0.5315(2) 0.0711(6) Uani d . . . 1 . .
H H9 0.3999 0.6576 0.5257 0.085 Uiso calc U . R 1 . .
C C10 0.4946(4) 0.7527(3) 0.6327(2) 0.0741(7) Uani d . . . 1 . .
H H10 0.4059 0.7333 0.695 0.089 Uiso calc U . R 1 . .
C C11 0.6294(4) 0.8265(3) 0.6409(2) 0.0665(6) Uani d . . . 1 . .
H H11 0.6301 0.8585 0.7085 0.08 Uiso calc U . R 1 . .
C C12 0.7625(3) 0.8536(2) 0.55053(18) 0.0544(5) Uani d . . . 1 . .
H H12 0.8538 0.9026 0.5576 0.065 Uiso calc U . R 1 . .
C C13 0.7975(3) 0.8399(2) 0.15137(17) 0.0507(5) Uani d . . . 1 . .
C C14 0.7841(3) 0.7037(2) 0.11370(17) 0.0467(4) Uani d . . . 1 . .
C C15 0.6826(3) 0.7138(3) 0.01591(19) 0.0600(6) Uani d . . . 1 . .
H H15 0.6106 0.8151 -0.0343 0.072 Uiso calc U . R 1 . .
C C16 0.6935(3) 0.5672(4) -0.0032(2) 0.0677(7) Uani d . . . 1 . .
H H16 0.6301 0.5697 -0.0685 0.081 Uiso calc U . R 1 . .
C C17 0.7975(3) 0.4170(3) 0.0736(2) 0.0651(6) Uani d . . . 1 . .
H H17 0.8008 0.3199 0.0598 0.078 Uiso calc U . R 1 . .
C C18 0.8966(3) 0.4077(3) 0.17045(19) 0.0531(5) Uani d . . . 1 . .
H H18 0.966 0.3058 0.2215 0.064 Uiso calc U . R 1 . .
C C19 0.8904(2) 0.5532(2) 0.18994(16) 0.0424(4) Uani d . . . 1 . .
C C20 0.9881(3) 0.5747(2) 0.28773(17) 0.0470(5) Uani d . . . 1 . .
H H20A 1.1243 0.5196 0.2885 0.056 Uiso calc U . R 1 . .
H H20B 0.9343 0.5302 0.367 0.056 Uiso calc U . R 1 . .
O O21 0.7146(3) 0.98573(19) 0.11397(15) 0.0781(5) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N5 . 1.447(3) ?
O1 S2 . 1.6441(18) ?
N5 C3 . 1.280(2) ?
C3 C7 . 1.470(3) ?
C3 C4 . 1.500(3) ?
C4 C20 . 1.529(2) ?
C4 C13 . 1.556(3) ?
C4 S2 . 1.861(2) ?
S2 O6 . 1.452(2) ?
C7 C12 . 1.396(3) ?
C7 C8 . 1.398(3) ?
C8 C9 . 1.377(3) ?
C8 H8 . 0.93 ?
C9 C10 . 1.383(4) ?
C9 H9 . 0.93 ?
C10 C11 . 1.374(4) ?
C10 H10 . 0.93 ?
C11 C12 . 1.369(3) ?
C11 H11 . 0.93 ?
C12 H12 . 0.93 ?
C13 O21 . 1.206(2) ?
C13 C14 . 1.462(3) ?
C14 C19 . 1.386(3) ?
C14 C15 . 1.398(3) ?
C15 C16 . 1.382(3) ?
C15 H15 . 0.93 ?
C16 C17 . 1.382(3) ?
C16 H16 . 0.93 ?
C17 C18 . 1.380(3) ?
C17 H17 . 0.93 ?
C18 C19 . 1.384(3) ?
C18 H18 . 0.93 ?
C19 C20 . 1.510(3) ?
C20 H20A . 0.97 ?
C20 H20B . 0.97 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N5 O1 S2 . . 114.49(11) ?
C3 N5 O1 . . 110.55(17) ?
N5 C3 C7 . . 118.89(17) ?
N5 C3 C4 . . 117.31(18) ?
C7 C3 C4 . . 123.68(16) ?
C3 C4 C20 . . 120.61(16) ?
C3 C4 C13 . . 111.60(16) ?
C20 C4 C13 . . 105.78(14) ?
C3 C4 S2 . . 101.99(12) ?
C20 C4 S2 . . 110.55(13) ?
C13 C4 S2 . . 105.40(12) ?
O6 S2 O1 . . 109.64(11) ?
O6 S2 C4 . . 106.86(10) ?
O1 S2 C4 . . 89.70(8) ?
C12 C7 C8 . . 118.8(2) ?
C12 C7 C3 . . 119.73(18) ?
C8 C7 C3 . . 121.40(17) ?
C9 C8 C7 . . 120.1(2) ?
C9 C8 H8 . . 119.9 ?
C7 C8 H8 . . 119.9 ?
C8 C9 C10 . . 120.3(2) ?
C8 C9 H9 . . 119.9 ?
C10 C9 H9 . . 119.9 ?
C11 C10 C9 . . 119.8(2) ?
C11 C10 H10 . . 120.1 ?
C9 C10 H10 . . 120.1 ?
C12 C11 C10 . . 120.7(2) ?
C12 C11 H11 . . 119.6 ?
C10 C11 H11 . . 119.6 ?
C11 C12 C7 . . 120.3(2) ?
C11 C12 H12 . . 119.9 ?
C7 C12 H12 . . 119.9 ?
O21 C13 C14 . . 129.91(19) ?
O21 C13 C4 . . 123.75(18) ?
C14 C13 C4 . . 106.33(15) ?
C19 C14 C15 . . 121.82(19) ?
C19 C14 C13 . . 110.41(16) ?
C15 C14 C13 . . 127.77(19) ?
C16 C15 C14 . . 117.4(2) ?
C16 C15 H15 . . 121.3 ?
C14 C15 H15 . . 121.3 ?
C17 C16 C15 . . 120.8(2) ?
C17 C16 H16 . . 119.6 ?
C15 C16 H16 . . 119.6 ?
C18 C17 C16 . . 121.5(2) ?
C18 C17 H17 . . 119.2 ?
C16 C17 H17 . . 119.2 ?
C17 C18 C19 . . 118.6(2) ?
C17 C18 H18 . . 120.7 ?
C19 C18 H18 . . 120.7 ?
C18 C19 C14 . . 119.81(18) ?
C18 C19 C20 . . 128.25(17) ?
C14 C19 C20 . . 111.94(16) ?
C19 C20 C4 . . 104.17(14) ?
C19 C20 H20A . . 110.9 ?
C4 C20 H20A . . 110.9 ?
C19 C20 H20B . . 110.9 ?
C4 C20 H20B . . 110.9 ?
H20A C20 H20B . . 108.9 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
S2 O1 N5 C3 . . . . -16.0(2) ?
O1 N5 C3 C7 . . . . -179.16(16) ?
O1 N5 C3 C4 . . . . -2.9(3) ?
N5 C3 C4 C20 . . . . 140.0(2) ?
C7 C3 C4 C20 . . . . -43.9(3) ?
N5 C3 C4 C13 . . . . -95.0(2) ?
C7 C3 C4 C13 . . . . 81.2(2) ?
N5 C3 C4 S2 . . . . 17.1(2) ?
C7 C3 C4 S2 . . . . -166.76(15) ?
N5 O1 S2 O6 . . . . -85.71(17) ?
N5 O1 S2 C4 . . . . 22.11(16) ?
C3 C4 S2 O6 . . . . 89.56(14) ?
C20 C4 S2 O6 . . . . -39.90(16) ?
C13 C4 S2 O6 . . . . -153.76(14) ?
C3 C4 S2 O1 . . . . -20.90(13) ?
C20 C4 S2 O1 . . . . -150.36(13) ?
C13 C4 S2 O1 . . . . 95.77(13) ?
N5 C3 C7 C12 . . . . -22.3(3) ?
C4 C3 C7 C12 . . . . 161.71(18) ?
N5 C3 C7 C8 . . . . 154.2(2) ?
C4 C3 C7 C8 . . . . -21.8(3) ?
C12 C7 C8 C9 . . . . -0.9(3) ?
C3 C7 C8 C9 . . . . -177.35(18) ?
C7 C8 C9 C10 . . . . 0.6(3) ?
C8 C9 C10 C11 . . . . 0.3(4) ?
C9 C10 C11 C12 . . . . -0.9(3) ?
C10 C11 C12 C7 . . . . 0.7(3) ?
C8 C7 C12 C11 . . . . 0.2(3) ?
C3 C7 C12 C11 . . . . 176.77(17) ?
C3 C4 C13 O21 . . . . 36.7(3) ?
C20 C4 C13 O21 . . . . 169.6(2) ?
S2 C4 C13 O21 . . . . -73.3(2) ?
C3 C4 C13 C14 . . . . -144.42(17) ?
C20 C4 C13 C14 . . . . -11.5(2) ?
S2 C4 C13 C14 . . . . 105.65(15) ?
O21 C13 C14 C19 . . . . -173.7(2) ?
C4 C13 C14 C19 . . . . 7.5(2) ?
O21 C13 C14 C15 . . . . 6.6(4) ?
C4 C13 C14 C15 . . . . -172.26(18) ?
C19 C14 C15 C16 . . . . -0.6(3) ?
C13 C14 C15 C16 . . . . 179.0(2) ?
C14 C15 C16 C17 . . . . 1.4(3) ?
C15 C16 C17 C18 . . . . -1.1(3) ?
C16 C17 C18 C19 . . . . 0.0(3) ?
C17 C18 C19 C14 . . . . 0.8(3) ?
C17 C18 C19 C20 . . . . -179.10(18) ?
C15 C14 C19 C18 . . . . -0.5(3) ?
C13 C14 C19 C18 . . . . 179.78(17) ?
C15 C14 C19 C20 . . . . 179.44(17) ?
C13 C14 C19 C20 . . . . -0.3(2) ?
C18 C19 C20 C4 . . . . 172.87(19) ?
C14 C19 C20 C4 . . . . -7.0(2) ?
C3 C4 C20 C19 . . . . 138.71(17) ?
C13 C4 C20 C19 . . . . 10.99(19) ?
S2 C4 C20 C19 . . . . -102.63(15) ?



