# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1881253'
_audit_update_record             
;
2018-11-24 deposited with the CCDC.	2019-03-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H30 N2 O6 S2'
_chemical_formula_weight         698.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4665(8)
_cell_length_b                   9.9099(8)
_cell_length_c                   20.0858(16)
_cell_angle_alpha                94.466(7)
_cell_angle_beta                 93.734(7)
_cell_angle_gamma                95.165(7)
_cell_volume                     1668.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3147
_cell_measurement_theta_min      3.3800
_cell_measurement_theta_max      23.7140

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.213
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.957
#_exptl_crystal_description                ''
_exptl_absorpt_correction_T_min  0.64701
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_reflns_number            15475
_diffrn_reflns_av_unetI/netI     0.0977
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.027
_diffrn_reflns_theta_max         28.833
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.863
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.863
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7546
_reflns_number_gt                3918
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0579P)²+0.2871P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7546
_refine_ls_number_parameters     451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1371
_refine_ls_R_factor_gt           0.0664
_refine_ls_wR_factor_ref         0.1849
_refine_ls_wR_factor_gt          0.1426
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.30562(11) 0.12439(8) 0.48722(4) 0.0470(3) Uani 1 1 d . . . . .
S2 S 0.30341(12) 0.64127(9) 0.89452(5) 0.0557(3) Uani 1 1 d . . . . .
O1 O -0.1809(3) 0.2429(2) 0.46596(11) 0.0460(6) Uani 1 1 d . . . . .
O2 O -0.2201(3) 0.0079(2) 0.48498(12) 0.0623(7) Uani 1 1 d . . . . .
O3 O -0.4478(3) 0.1231(2) 0.44571(12) 0.0612(7) Uani 1 1 d . . . . .
O4 O 0.3295(3) 0.7628(2) 0.95297(11) 0.0546(6) Uani 1 1 d . . . . .
O5 O 0.3546(4) 0.5271(3) 0.92487(14) 0.0819(9) Uani 1 1 d . . . . .
O6 O 0.1439(3) 0.6373(3) 0.86727(14) 0.0751(8) Uani 1 1 d . . . . .
N1 N -0.3351(3) 0.1703(3) 0.56356(14) 0.0488(7) Uani 1 1 d . . . . .
N2 N 0.4231(3) 0.6854(3) 0.83902(14) 0.0521(8) Uani 1 1 d . . . . .
C1 C -0.2172(4) 0.3762(3) 0.48225(16) 0.0392(8) Uani 1 1 d . . . . .
C2 C -0.1657(4) 0.4715(3) 0.43781(16) 0.0409(8) Uani 1 1 d . . . . .
C3 C -0.0942(4) 0.4361(4) 0.37821(18) 0.0510(9) Uani 1 1 d . . . . .
H3 H -0.0756 0.3463 0.3671 0.061 Uiso 1 1 calc R U . . .
C4 C -0.0522(5) 0.5345(4) 0.3369(2) 0.0638(11) Uani 1 1 d . . . . .
H4 H -0.0084 0.5109 0.2968 0.077 Uiso 1 1 calc R U . . .
C5 C -0.0748(5) 0.6701(4) 0.3543(2) 0.0685(11) Uani 1 1 d . . . . .
H5 H -0.0433 0.7360 0.3261 0.082 Uiso 1 1 calc R U . . .
C6 C -0.1411(5) 0.7075(4) 0.4111(2) 0.0586(10) Uani 1 1 d . . . . .
H6 H -0.1533 0.7988 0.4218 0.070 Uiso 1 1 calc R U . . .
C7 C -0.1928(4) 0.6097(3) 0.45487(18) 0.0466(9) Uani 1 1 d . . . . .
C8 C -0.2684(4) 0.6434(3) 0.51283(18) 0.0546(10) Uani 1 1 d . . . . .
H8 H -0.2861 0.7335 0.5236 0.066 Uiso 1 1 calc R U . . .
C9 C -0.3166(4) 0.5470(3) 0.55394(18) 0.0535(10) Uani 1 1 d . . . . .
H9 H -0.3673 0.5727 0.5920 0.064 Uiso 1 1 calc R U . . .
C10 C -0.2909(4) 0.4068(3) 0.53982(16) 0.0437(8) Uani 1 1 d . . . . .
C11 C -0.3340(4) 0.3006(3) 0.58276(16) 0.0438(8) Uani 1 1 d . . . . .
C12 C -0.3759(4) 0.3322(4) 0.65147(17) 0.0534(9) Uani 1 1 d . . . . .
H12 H -0.3690 0.4289 0.6671 0.064 Uiso 1 1 calc R U . . .
C13 C -0.5030(5) 0.2419(5) 0.6791(2) 0.0835(14) Uani 1 1 d . . . . .
H13A H -0.5729 0.2845 0.7091 0.100 Uiso 1 1 calc R U . . .
H13B H -0.5537 0.1653 0.6500 0.100 Uiso 1 1 calc R U . . .
C14 C -0.3374(4) 0.2353(4) 0.70430(18) 0.0547(9) Uani 1 1 d . . . . .
H14 H -0.2904 0.1541 0.6869 0.066 Uiso 1 1 calc R U . . .
C15 C -0.2716(4) 0.2898(4) 0.77266(17) 0.0517(9) Uani 1 1 d . . . . .
C16 C -0.1323(5) 0.2442(4) 0.7980(2) 0.0682(12) Uani 1 1 d . . . . .
H16 H -0.0835 0.1792 0.7729 0.082 Uiso 1 1 calc R U . . .
C17 C -0.0655(5) 0.2944(5) 0.8601(2) 0.0807(13) Uani 1 1 d . . . . .
H17 H 0.0300 0.2652 0.8763 0.097 Uiso 1 1 calc R U . . .
C18 C -0.1391(6) 0.3876(5) 0.8987(2) 0.0794(13) Uani 1 1 d . . . . .
H18 H -0.0946 0.4203 0.9411 0.095 Uiso 1 1 calc R U . . .
C19 C -0.2774(6) 0.4315(4) 0.8743(2) 0.0777(13) Uani 1 1 d . . . . .
H19 H -0.3281 0.4939 0.9003 0.093 Uiso 1 1 calc R U . . .
C20 C -0.3422(5) 0.3848(4) 0.8120(2) 0.0629(11) Uani 1 1 d . . . . .
H20 H -0.4355 0.4174 0.7956 0.075 Uiso 1 1 calc R U . . .
C21 C 0.3412(4) 0.8954(3) 0.93323(16) 0.0417(8) Uani 1 1 d . . . . .
C22 C 0.2860(4) 0.9936(3) 0.97859(16) 0.0426(8) Uani 1 1 d . . . . .
C23 C 0.2148(4) 0.9609(4) 1.03714(17) 0.0558(10) Uani 1 1 d . . . . .
H23 H 0.2048 0.8714 1.0483 0.067 Uiso 1 1 calc R U . . .
C24 C 0.1605(5) 1.0602(4) 1.0775(2) 0.0677(11) Uani 1 1 d . . . . .
H24 H 0.1122 1.0379 1.1159 0.081 Uiso 1 1 calc R U . . .
C25 C 0.1760(5) 1.1962(4) 1.0619(2) 0.0660(11) Uani 1 1 d . . . . .
H25 H 0.1379 1.2629 1.0901 0.079 Uiso 1 1 calc R U . . .
C26 C 0.2463(5) 1.2309(4) 1.00610(19) 0.0594(10) Uani 1 1 d . . . . .
H26 H 0.2565 1.3214 0.9965 0.071 Uiso 1 1 calc R U . . .
C27 C 0.3046(4) 1.1310(3) 0.96207(17) 0.0460(8) Uani 1 1 d . . . . .
C28 C 0.3739(4) 1.1620(4) 0.90270(19) 0.0559(10) Uani 1 1 d . . . . .
H28 H 0.3866 1.2519 0.8922 0.067 Uiso 1 1 calc R U . . .
C29 C 0.4225(4) 1.0633(3) 0.86044(18) 0.0543(9) Uani 1 1 d . . . . .
H29 H 0.4681 1.0869 0.8216 0.065 Uiso 1 1 calc R U . . .
C30 C 0.4053(4) 0.9239(3) 0.87424(16) 0.0402(8) Uani 1 1 d . . . . .
C31 C 0.4536(4) 0.8141(4) 0.82976(17) 0.0445(8) Uani 1 1 d . . . . .
C32 C 0.5373(4) 0.8445(4) 0.76994(16) 0.0483(9) Uani 1 1 d . . . . .
H32 H 0.5580 0.9410 0.7627 0.058 Uiso 1 1 calc R U . . .
C33 C 0.4989(5) 0.7480(5) 0.70749(19) 0.0725(12) Uani 1 1 d . . . . .
H33A H 0.4244 0.6688 0.7104 0.087 Uiso 1 1 calc R U . . .
H33B H 0.4929 0.7872 0.6647 0.087 Uiso 1 1 calc R U . . .
C34 C 0.6564(4) 0.7513(4) 0.74318(17) 0.0481(9) Uani 1 1 d . . . . .
H34 H 0.6713 0.6729 0.7690 0.058 Uiso 1 1 calc R U . . .
C35 C 0.8042(4) 0.8152(3) 0.71867(16) 0.0427(8) Uani 1 1 d . . . . .
C36 C 0.8077(4) 0.8880(3) 0.66239(17) 0.0480(9) Uani 1 1 d . . . . .
H36 H 0.7129 0.8957 0.6375 0.058 Uiso 1 1 calc R U . . .
C37 C 0.9467(5) 0.9491(4) 0.64237(19) 0.0565(10) Uani 1 1 d . . . . .
H37 H 0.9449 0.9950 0.6037 0.068 Uiso 1 1 calc R U . . .
C38 C 1.0877(5) 0.9431(4) 0.6788(2) 0.0640(11) Uani 1 1 d . . . . .
H38 H 1.1816 0.9869 0.6662 0.077 Uiso 1 1 calc R U . . .
C39 C 1.0872(5) 0.8706(5) 0.7344(2) 0.0735(13) Uani 1 1 d . . . . .
H39 H 1.1826 0.8650 0.7593 0.088 Uiso 1 1 calc R U . . .
C40 C 0.9496(4) 0.8061(4) 0.75439(17) 0.0600(11) Uani 1 1 d . . . . .
H40 H 0.9534 0.7563 0.7917 0.072 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.416(2) . ?
S1 O3 1.417(2) . ?
S1 N1 1.607(3) . ?
S1 O1 1.610(2) . ?
S2 O5 1.414(2) . ?
S2 O6 1.420(3) . ?
S2 O4 1.605(2) . ?
S2 N2 1.614(3) . ?
O1 C1 1.402(3) . ?
O4 C21 1.399(4) . ?
N1 C11 1.318(4) . ?
N2 C31 1.308(4) . ?
C1 C10 1.376(4) . ?
C1 C2 1.409(4) . ?
C2 C3 1.411(4) . ?
C2 C7 1.428(4) . ?
C3 C4 1.367(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.395(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.345(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.418(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.397(5) . ?
C8 C9 1.363(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.435(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.448(5) . ?
C11 C12 1.464(4) . ?
C12 C13 1.500(5) . ?
C12 C14 1.525(5) . ?
C12 H12 0.9800 . ?
C13 C14 1.468(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.489(5) . ?
C14 H14 0.9800 . ?
C15 C16 1.382(5) . ?
C15 C20 1.384(5) . ?
C16 C17 1.372(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.378(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.361(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.362(5) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C30 1.373(4) . ?
C21 C22 1.412(4) . ?
C22 C23 1.403(5) . ?
C22 C27 1.424(5) . ?
C23 C24 1.357(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.403(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.356(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.419(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.406(5) . ?
C28 C29 1.355(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.426(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.458(4) . ?
C31 C32 1.472(5) . ?
C32 C33 1.516(5) . ?
C32 C34 1.523(4) . ?
C32 H32 0.9800 . ?
C33 C34 1.469(5) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.482(5) . ?
C34 H34 0.9800 . ?
C35 C36 1.388(5) . ?
C35 C40 1.398(4) . ?
C36 C37 1.372(5) . ?
C36 H36 0.9300 . ?
C37 C38 1.367(5) . ?
C37 H37 0.9300 . ?
C38 C39 1.375(6) . ?
C38 H38 0.9300 . ?
C39 C40 1.376(6) . ?
C39 H39 0.9300 . ?
C40 H40 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O3 119.33(15) . . ?
O2 S1 N1 109.62(15) . . ?
O3 S1 N1 110.49(16) . . ?
O2 S1 O1 103.97(14) . . ?
O3 S1 O1 107.91(15) . . ?
N1 S1 O1 104.27(13) . . ?
O5 S2 O6 119.45(19) . . ?
O5 S2 O4 104.57(16) . . ?
O6 S2 O4 107.25(15) . . ?
O5 S2 N2 109.89(16) . . ?
O6 S2 N2 109.54(17) . . ?
O4 S2 N2 105.08(15) . . ?
C1 O1 S1 115.7(2) . . ?
C21 O4 S2 116.9(2) . . ?
C11 N1 S1 119.5(2) . . ?
C31 N2 S2 119.8(2) . . ?
C10 C1 O1 119.9(3) . . ?
C10 C1 C2 124.9(3) . . ?
O1 C1 C2 115.0(3) . . ?
C1 C2 C3 123.5(3) . . ?
C1 C2 C7 116.6(3) . . ?
C3 C2 C7 120.0(3) . . ?
C4 C3 C2 119.6(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.5(4) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 121.3(4) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 121.0(3) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C8 C7 C6 122.8(3) . . ?
C8 C7 C2 119.7(3) . . ?
C6 C7 C2 117.5(3) . . ?
C9 C8 C7 121.4(3) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 121.5(3) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C1 C10 C9 116.0(3) . . ?
C1 C10 C11 119.9(3) . . ?
C9 C10 C11 124.1(3) . . ?
N1 C11 C10 122.8(3) . . ?
N1 C11 C12 115.6(3) . . ?
C10 C11 C12 121.6(3) . . ?
C11 C12 C13 118.9(3) . . ?
C11 C12 C14 119.0(3) . . ?
C13 C12 C14 58.0(2) . . ?
C11 C12 H12 116.1 . . ?
C13 C12 H12 116.1 . . ?
C14 C12 H12 116.1 . . ?
C14 C13 C12 61.8(3) . . ?
C14 C13 H13A 117.6 . . ?
C12 C13 H13A 117.6 . . ?
C14 C13 H13B 117.6 . . ?
C12 C13 H13B 117.6 . . ?
H13A C13 H13B 114.7 . . ?
C13 C14 C15 123.8(3) . . ?
C13 C14 C12 60.2(3) . . ?
C15 C14 C12 120.2(3) . . ?
C13 C14 H14 114.1 . . ?
C15 C14 H14 114.1 . . ?
C12 C14 H14 114.1 . . ?
C16 C15 C20 118.2(4) . . ?
C16 C15 C14 118.5(3) . . ?
C20 C15 C14 123.3(3) . . ?
C17 C16 C15 120.3(4) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 120.4(4) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 119.4(4) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C20 C19 C18 120.5(4) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C15 121.1(4) . . ?
C19 C20 H20 119.4 . . ?
C15 C20 H20 119.4 . . ?
C30 C21 O4 120.6(3) . . ?
C30 C21 C22 124.3(3) . . ?
O4 C21 C22 115.1(3) . . ?
C23 C22 C21 123.1(3) . . ?
C23 C22 C27 120.2(3) . . ?
C21 C22 C27 116.6(3) . . ?
C24 C23 C22 119.9(4) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C23 C24 C25 121.0(4) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C26 C25 C24 120.4(4) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C25 C26 C27 121.0(4) . . ?
C25 C26 H26 119.5 . . ?
C27 C26 H26 119.5 . . ?
C28 C27 C26 122.8(3) . . ?
C28 C27 C22 119.6(3) . . ?
C26 C27 C22 117.6(3) . . ?
C29 C28 C27 121.2(3) . . ?
C29 C28 H28 119.4 . . ?
C27 C28 H28 119.4 . . ?
C28 C29 C30 121.5(3) . . ?
C28 C29 H29 119.3 . . ?
C30 C29 H29 119.3 . . ?
C21 C30 C29 116.7(3) . . ?
C21 C30 C31 119.9(3) . . ?
C29 C30 C31 123.4(3) . . ?
N2 C31 C30 123.2(3) . . ?
N2 C31 C32 116.4(3) . . ?
C30 C31 C32 120.4(3) . . ?
C31 C32 C33 117.5(3) . . ?
C31 C32 C34 120.7(3) . . ?
C33 C32 C34 57.8(2) . . ?
C31 C32 H32 116.1 . . ?
C33 C32 H32 116.1 . . ?
C34 C32 H32 116.1 . . ?
C34 C33 C32 61.3(2) . . ?
C34 C33 H33A 117.6 . . ?
C32 C33 H33A 117.6 . . ?
C34 C33 H33B 117.6 . . ?
C32 C33 H33B 117.6 . . ?
H33A C33 H33B 114.7 . . ?
C33 C34 C35 123.7(3) . . ?
C33 C34 C32 60.8(2) . . ?
C35 C34 C32 117.9(3) . . ?
C33 C34 H34 114.6 . . ?
C35 C34 H34 114.6 . . ?
C32 C34 H34 114.6 . . ?
C36 C35 C40 116.9(3) . . ?
C36 C35 C34 123.8(3) . . ?
C40 C35 C34 119.2(3) . . ?
C37 C36 C35 122.1(3) . . ?
C37 C36 H36 119.0 . . ?
C35 C36 H36 119.0 . . ?
C38 C37 C36 120.6(4) . . ?
C38 C37 H37 119.7 . . ?
C36 C37 H37 119.7 . . ?
C37 C38 C39 118.3(4) . . ?
C37 C38 H38 120.8 . . ?
C39 C38 H38 120.8 . . ?
C38 C39 C40 121.9(4) . . ?
C38 C39 H39 119.0 . . ?
C40 C39 H39 119.0 . . ?
C39 C40 C35 120.2(4) . . ?
C39 C40 H40 119.9 . . ?
C35 C40 H40 119.9 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 O1 C1 -162.4(2) . . . . ?
O3 S1 O1 C1 70.0(2) . . . . ?
N1 S1 O1 C1 -47.5(2) . . . . ?
O5 S2 O4 C21 158.8(2) . . . . ?
O6 S2 O4 C21 -73.5(3) . . . . ?
N2 S2 O4 C21 43.1(3) . . . . ?
O2 S1 N1 C11 145.1(3) . . . . ?
O3 S1 N1 C11 -81.4(3) . . . . ?
O1 S1 N1 C11 34.3(3) . . . . ?
O5 S2 N2 C31 -145.0(3) . . . . ?
O6 S2 N2 C31 81.9(3) . . . . ?
O4 S2 N2 C31 -33.0(3) . . . . ?
S1 O1 C1 C10 34.1(4) . . . . ?
S1 O1 C1 C2 -148.8(2) . . . . ?
C10 C1 C2 C3 -178.3(3) . . . . ?
O1 C1 C2 C3 4.9(4) . . . . ?
C10 C1 C2 C7 0.2(5) . . . . ?
O1 C1 C2 C7 -176.6(3) . . . . ?
C1 C2 C3 C4 178.0(3) . . . . ?
C7 C2 C3 C4 -0.5(5) . . . . ?
C2 C3 C4 C5 2.2(6) . . . . ?
C3 C4 C5 C6 -1.5(6) . . . . ?
C4 C5 C6 C7 -0.9(6) . . . . ?
C5 C6 C7 C8 -177.2(4) . . . . ?
C5 C6 C7 C2 2.5(5) . . . . ?
C1 C2 C7 C8 -0.6(5) . . . . ?
C3 C2 C7 C8 177.9(3) . . . . ?
C1 C2 C7 C6 179.6(3) . . . . ?
C3 C2 C7 C6 -1.8(5) . . . . ?
C6 C7 C8 C9 -180.0(3) . . . . ?
C2 C7 C8 C9 0.3(5) . . . . ?
C7 C8 C9 C10 0.5(6) . . . . ?
O1 C1 C10 C9 177.2(3) . . . . ?
C2 C1 C10 C9 0.4(5) . . . . ?
O1 C1 C10 C11 -1.3(5) . . . . ?
C2 C1 C10 C11 -178.0(3) . . . . ?
C8 C9 C10 C1 -0.8(5) . . . . ?
C8 C9 C10 C11 177.6(3) . . . . ?
S1 N1 C11 C10 -6.6(5) . . . . ?
S1 N1 C11 C12 174.8(2) . . . . ?
C1 C10 C11 N1 -13.8(5) . . . . ?
C9 C10 C11 N1 167.9(3) . . . . ?
C1 C10 C11 C12 164.7(3) . . . . ?
C9 C10 C11 C12 -13.6(5) . . . . ?
N1 C11 C12 C13 -37.4(5) . . . . ?
C10 C11 C12 C13 144.0(4) . . . . ?
N1 C11 C12 C14 30.0(5) . . . . ?
C10 C11 C12 C14 -148.6(3) . . . . ?
C11 C12 C13 C14 107.9(4) . . . . ?
C12 C13 C14 C15 108.3(4) . . . . ?
C11 C12 C14 C13 -107.8(4) . . . . ?
C11 C12 C14 C15 138.1(4) . . . . ?
C13 C12 C14 C15 -114.1(4) . . . . ?
C13 C14 C15 C16 161.2(4) . . . . ?
C12 C14 C15 C16 -126.5(4) . . . . ?
C13 C14 C15 C20 -19.4(6) . . . . ?
C12 C14 C15 C20 52.9(5) . . . . ?
C20 C15 C16 C17 -1.1(6) . . . . ?
C14 C15 C16 C17 178.4(4) . . . . ?
C15 C16 C17 C18 2.0(7) . . . . ?
C16 C17 C18 C19 -1.1(7) . . . . ?
C17 C18 C19 C20 -0.6(7) . . . . ?
C18 C19 C20 C15 1.5(7) . . . . ?
C16 C15 C20 C19 -0.6(6) . . . . ?
C14 C15 C20 C19 179.9(4) . . . . ?
S2 O4 C21 C30 -31.3(4) . . . . ?
S2 O4 C21 C22 149.9(2) . . . . ?
C30 C21 C22 C23 177.2(3) . . . . ?
O4 C21 C22 C23 -4.1(5) . . . . ?
C30 C21 C22 C27 -2.3(5) . . . . ?
O4 C21 C22 C27 176.4(3) . . . . ?
C21 C22 C23 C24 -178.1(3) . . . . ?
C27 C22 C23 C24 1.3(5) . . . . ?
C22 C23 C24 C25 -0.7(6) . . . . ?
C23 C24 C25 C26 -0.2(6) . . . . ?
C24 C25 C26 C27 0.4(6) . . . . ?
C25 C26 C27 C28 178.0(4) . . . . ?
C25 C26 C27 C22 0.2(5) . . . . ?
C23 C22 C27 C28 -179.0(3) . . . . ?
C21 C22 C27 C28 0.5(5) . . . . ?
C23 C22 C27 C26 -1.1(5) . . . . ?
C21 C22 C27 C26 178.4(3) . . . . ?
C26 C27 C28 C29 -177.3(3) . . . . ?
C22 C27 C28 C29 0.5(5) . . . . ?
C27 C28 C29 C30 0.1(6) . . . . ?
O4 C21 C30 C29 -175.8(3) . . . . ?
C22 C21 C30 C29 2.9(5) . . . . ?
O4 C21 C30 C31 3.5(5) . . . . ?
C22 C21 C30 C31 -177.8(3) . . . . ?
C28 C29 C30 C21 -1.7(5) . . . . ?
C28 C29 C30 C31 179.0(3) . . . . ?
S2 N2 C31 C30 10.1(5) . . . . ?
S2 N2 C31 C32 -168.2(2) . . . . ?
C21 C30 C31 N2 8.0(5) . . . . ?
C29 C30 C31 N2 -172.8(3) . . . . ?
C21 C30 C31 C32 -173.7(3) . . . . ?
C29 C30 C31 C32 5.5(5) . . . . ?
N2 C31 C32 C33 35.1(4) . . . . ?
C30 C31 C32 C33 -143.3(3) . . . . ?
N2 C31 C32 C34 -32.0(5) . . . . ?
C30 C31 C32 C34 149.6(3) . . . . ?
C31 C32 C33 C34 -110.6(3) . . . . ?
C32 C33 C34 C35 -105.7(4) . . . . ?
C31 C32 C34 C33 105.2(4) . . . . ?
C31 C32 C34 C35 -139.8(3) . . . . ?
C33 C32 C34 C35 115.0(4) . . . . ?
C33 C34 C35 C36 5.4(5) . . . . ?
C32 C34 C35 C36 -66.6(4) . . . . ?
C33 C34 C35 C40 -176.3(3) . . . . ?
C32 C34 C35 C40 111.7(4) . . . . ?
C40 C35 C36 C37 -0.2(5) . . . . ?
C34 C35 C36 C37 178.1(3) . . . . ?
C35 C36 C37 C38 -1.8(5) . . . . ?
C36 C37 C38 C39 2.2(5) . . . . ?
C37 C38 C39 C40 -0.7(6) . . . . ?
C38 C39 C40 C35 -1.3(6) . . . . ?
C36 C35 C40 C39 1.7(5) . . . . ?
C34 C35 C40 C39 -176.7(3) . . . . ?

_refine_diff_density_max         0.231
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1881255'
_audit_update_record             
;
2018-11-24 deposited with the CCDC.	2019-03-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H15 N O3 S'
_chemical_formula_weight         325.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   13.1858(4)
_cell_length_b                   8.0088(2)
_cell_length_c                   15.5088(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.498(3)
_cell_angle_gamma                90
_cell_volume                     1561.98(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3707
_cell_measurement_theta_min      3.1000
_cell_measurement_theta_max      25.4460

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.222
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_T_min  0.89606
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.799
_oxdiff_exptl_absorpt_empirical_full_max 1.198
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_reflns_number            14747
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.892
_diffrn_reflns_theta_max         28.935
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.904
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3730
_reflns_number_gt                2411
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0588P)²+0.7010P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3730
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0955
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.1623
_refine_ls_wR_factor_gt          0.1391
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.27008(6) 0.78612(8) 0.59341(5) 0.0535(2) Uani 1 1 d . . . . .
O1 O 0.17675(16) 0.7411(2) 0.63533(13) 0.0566(5) Uani 1 1 d . . . . .
O2 O 0.22950(17) 0.7773(3) 0.49836(14) 0.0682(6) Uani 1 1 d . . . . .
O3 O 0.30959(19) 0.9402(2) 0.63422(18) 0.0833(8) Uani 1 1 d . . . . .
N1 N 0.35869(17) 0.6447(2) 0.62948(15) 0.0482(6) Uani 1 1 d . . . . .
C1 C 0.1463(2) 0.5735(3) 0.63094(16) 0.0429(6) Uani 1 1 d . . . . .
C2 C 0.0425(2) 0.5397(4) 0.62409(19) 0.0570(7) Uani 1 1 d . . . . .
H2 H -0.0059 0.6260 0.6200 0.068 Uiso 1 1 calc R U . . .
C3 C 0.0111(2) 0.3757(4) 0.6234(2) 0.0658(8) Uani 1 1 d . . . . .
H3 H -0.0593 0.3508 0.6185 0.079 Uiso 1 1 calc R U . . .
C4 C 0.0832(3) 0.2481(4) 0.6301(2) 0.0643(8) Uani 1 1 d . . . . .
H4 H 0.0614 0.1377 0.6299 0.077 Uiso 1 1 calc R U . . .
C5 C 0.1869(2) 0.2835(3) 0.63702(18) 0.0505(7) Uani 1 1 d . . . . .
H5 H 0.2347 0.1963 0.6411 0.061 Uiso 1 1 calc R U . . .
C6 C 0.22228(19) 0.4482(3) 0.63811(15) 0.0380(5) Uani 1 1 d . . . . .
C7 C 0.33118(19) 0.4930(3) 0.64380(15) 0.0384(5) Uani 1 1 d . . . . .
C8 C 0.41598(19) 0.3676(3) 0.66554(16) 0.0394(6) Uani 1 1 d . . . . .
H8 H 0.3983 0.2574 0.6845 0.047 Uiso 1 1 calc R U . . .
C9 C 0.53133(19) 0.4271(3) 0.70603(15) 0.0397(6) Uani 1 1 d . . . . .
H9 H 0.5405 0.5479 0.7153 0.048 Uiso 1 1 calc R U . . .
C10 C 0.4948(2) 0.3724(3) 0.61109(16) 0.0475(6) Uani 1 1 d . . . . .
H10 H 0.4832 0.4624 0.5664 0.057 Uiso 1 1 calc R U . . .
C11 C 0.5402(2) 0.2143(4) 0.58562(19) 0.0638(9) Uani 1 1 d . . . . .
H11A H 0.6038 0.2411 0.5693 0.077 Uiso 1 1 calc R U . . .
H11B H 0.4890 0.1661 0.5329 0.077 Uiso 1 1 calc R U . . .
C12 C 0.5680(2) 0.0851(4) 0.6614(2) 0.0585(8) Uani 1 1 d . . . . .
H12A H 0.5029 0.0357 0.6666 0.070 Uiso 1 1 calc R U . . .
H12B H 0.6097 -0.0033 0.6459 0.070 Uiso 1 1 calc R U . . .
C13 C 0.6294(2) 0.1584(3) 0.75121(17) 0.0451(6) Uani 1 1 d . . . . .
C14 C 0.7052(2) 0.0663(4) 0.8151(2) 0.0570(7) Uani 1 1 d . . . . .
H14 H 0.7202 -0.0420 0.8010 0.068 Uiso 1 1 calc R U . . .
C15 C 0.7585(2) 0.1307(4) 0.8981(2) 0.0674(9) Uani 1 1 d . . . . .
H15 H 0.8083 0.0660 0.9399 0.081 Uiso 1 1 calc R U . . .
C16 C 0.7382(2) 0.2913(4) 0.9195(2) 0.0611(8) Uani 1 1 d . . . . .
H16 H 0.7741 0.3357 0.9758 0.073 Uiso 1 1 calc R U . . .
C17 C 0.6641(2) 0.3864(3) 0.85689(17) 0.0493(7) Uani 1 1 d . . . . .
H17 H 0.6513 0.4956 0.8711 0.059 Uiso 1 1 calc R U . . .
C18 C 0.60885(19) 0.3215(3) 0.77342(15) 0.0391(6) 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
S1 O2 1.411(2) . ?
S1 O3 1.413(2) . ?
S1 O1 1.596(2) . ?
S1 N1 1.603(2) . ?
O1 C1 1.397(3) . ?
N1 C7 1.306(3) . ?
C1 C2 1.367(4) . ?
C1 C6 1.398(3) . ?
C2 C3 1.377(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.398(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.457(3) . ?
C7 C8 1.465(3) . ?
C8 C10 1.524(3) . ?
C8 C9 1.536(3) . ?
C8 H8 0.9800 . ?
C9 C10 1.472(3) . ?
C9 C18 1.487(3) . ?
C9 H9 0.9800 . ?
C10 C11 1.504(4) . ?
C10 H10 0.9800 . ?
C11 C12 1.526(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.504(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.389(4) . ?
C13 C18 1.398(3) . ?
C14 C15 1.368(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.375(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.380(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.382(3) . ?
C17 H17 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O3 119.00(14) . . ?
O2 S1 O1 108.52(13) . . ?
O3 S1 O1 103.92(14) . . ?
O2 S1 N1 109.70(13) . . ?
O3 S1 N1 109.20(13) . . ?
O1 S1 N1 105.58(11) . . ?
C1 O1 S1 116.28(16) . . ?
C7 N1 S1 120.41(19) . . ?
C2 C1 O1 117.4(2) . . ?
C2 C1 C6 122.7(3) . . ?
O1 C1 C6 119.8(2) . . ?
C1 C2 C3 118.8(3) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 121.2(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 116.6(2) . . ?
C5 C6 C7 123.5(2) . . ?
C1 C6 C7 119.8(2) . . ?
N1 C7 C6 122.5(2) . . ?
N1 C7 C8 116.4(2) . . ?
C6 C7 C8 121.0(2) . . ?
C7 C8 C10 117.1(2) . . ?
C7 C8 C9 118.3(2) . . ?
C10 C8 C9 57.49(16) . . ?
C7 C8 H8 116.9 . . ?
C10 C8 H8 116.9 . . ?
C9 C8 H8 116.9 . . ?
C10 C9 C18 118.9(2) . . ?
C10 C9 C8 60.82(16) . . ?
C18 C9 C8 119.8(2) . . ?
C10 C9 H9 115.5 . . ?
C18 C9 H9 115.5 . . ?
C8 C9 H9 115.5 . . ?
C9 C10 C11 118.5(2) . . ?
C9 C10 C8 61.69(16) . . ?
C11 C10 C8 121.1(2) . . ?
C9 C10 H10 115.1 . . ?
C11 C10 H10 115.1 . . ?
C8 C10 H10 115.1 . . ?
C10 C11 C12 113.0(2) . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 112.7(2) . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 C18 118.2(2) . . ?
C14 C13 C12 121.6(2) . . ?
C18 C13 C12 120.2(2) . . ?
C15 C14 C13 121.8(3) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C14 C15 C16 119.8(3) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C17 119.6(3) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C16 C17 C18 120.9(3) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C17 C18 C13 119.7(2) . . ?
C17 C18 C9 120.1(2) . . ?
C13 C18 C9 120.1(2) . . ?

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
O2 S1 O1 C1 72.7(2) . . . . ?
O3 S1 O1 C1 -159.73(18) . . . . ?
N1 S1 O1 C1 -44.8(2) . . . . ?
O2 S1 N1 C7 -84.6(2) . . . . ?
O3 S1 N1 C7 143.4(2) . . . . ?
O1 S1 N1 C7 32.2(2) . . . . ?
S1 O1 C1 C2 -149.4(2) . . . . ?
S1 O1 C1 C6 33.7(3) . . . . ?
O1 C1 C2 C3 -177.3(2) . . . . ?
C6 C1 C2 C3 -0.6(4) . . . . ?
C1 C2 C3 C4 0.4(5) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?
C4 C5 C6 C1 -0.6(4) . . . . ?
C4 C5 C6 C7 -178.9(3) . . . . ?
C2 C1 C6 C5 0.7(4) . . . . ?
O1 C1 C6 C5 177.3(2) . . . . ?
C2 C1 C6 C7 179.1(2) . . . . ?
O1 C1 C6 C7 -4.3(3) . . . . ?
S1 N1 C7 C6 -7.1(3) . . . . ?
S1 N1 C7 C8 172.45(17) . . . . ?
C5 C6 C7 N1 168.1(2) . . . . ?
C1 C6 C7 N1 -10.2(4) . . . . ?
C5 C6 C7 C8 -11.4(4) . . . . ?
C1 C6 C7 C8 170.3(2) . . . . ?
N1 C7 C8 C10 -42.1(3) . . . . ?
C6 C7 C8 C10 137.4(2) . . . . ?
N1 C7 C8 C9 23.7(3) . . . . ?
C6 C7 C8 C9 -156.8(2) . . . . ?
C7 C8 C9 C10 -105.7(2) . . . . ?
C7 C8 C9 C18 145.8(2) . . . . ?
C10 C8 C9 C18 -108.5(3) . . . . ?
C18 C9 C10 C11 -1.9(4) . . . . ?
C8 C9 C10 C11 -112.0(3) . . . . ?
C18 C9 C10 C8 110.1(2) . . . . ?
C7 C8 C10 C9 107.8(2) . . . . ?
C7 C8 C10 C11 -144.2(2) . . . . ?
C9 C8 C10 C11 108.0(3) . . . . ?
C9 C10 C11 C12 31.9(4) . . . . ?
C8 C10 C11 C12 -40.4(4) . . . . ?
C10 C11 C12 C13 -47.2(3) . . . . ?
C11 C12 C13 C14 -147.4(3) . . . . ?
C11 C12 C13 C18 34.5(4) . . . . ?
C18 C13 C14 C15 0.5(4) . . . . ?
C12 C13 C14 C15 -177.6(3) . . . . ?
C13 C14 C15 C16 -0.7(5) . . . . ?
C14 C15 C16 C17 -0.1(5) . . . . ?
C15 C16 C17 C18 1.0(5) . . . . ?
C16 C17 C18 C13 -1.2(4) . . . . ?
C16 C17 C18 C9 -178.5(2) . . . . ?
C14 C13 C18 C17 0.4(4) . . . . ?
C12 C13 C18 C17 178.6(3) . . . . ?
C14 C13 C18 C9 177.7(2) . . . . ?
C12 C13 C18 C9 -4.1(4) . . . . ?
C10 C9 C18 C17 164.2(2) . . . . ?
C8 C9 C18 C17 -124.8(3) . . . . ?
C10 C9 C18 C13 -13.1(4) . . . . ?
C8 C9 C18 C13 57.9(3) . . . . ?

_refine_diff_density_max         0.203
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1881254'
_audit_update_record             
;
2018-11-24 deposited with the CCDC.	2019-03-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24.75 H22.50 F2 N O4 S2'
_chemical_formula_weight         500.06

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   13.2102(5)
_cell_length_b                   11.1069(3)
_cell_length_c                   15.6812(6)
_cell_angle_alpha                90
_cell_angle_beta                 106.801(4)
_cell_angle_gamma                90
_cell_volume                     2202.60(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7473
_cell_measurement_theta_min      3.7150
_cell_measurement_theta_max      28.2910

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.293
_shelx_estimated_absorpt_T_min   0.909
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_T_min  0.85714
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.820
_oxdiff_exptl_absorpt_empirical_full_max 1.326
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;


_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_reflns_number            17722
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.276
_diffrn_reflns_theta_max         29.142
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.878
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.878
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5225
_reflns_number_gt                3769
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_refine_special_details          ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0734P)²+0.8312P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5225
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.1635
_refine_ls_wR_factor_gt          0.1400
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.20422(5) 0.35174(5) 0.53937(5) 0.0498(2) Uani 1 1 d . . . . .
S2 S 0.45515(6) 0.87416(6) 0.37977(5) 0.0535(2) Uani 1 1 d . . . . .
F1 F 0.55416(18) 0.9128(3) 0.44208(15) 0.1119(9) Uani 1 1 d . . . . .
O1 O 0.11039(16) 0.30884(17) 0.55362(16) 0.0727(6) Uani 1 1 d . . . . .
O2 O 0.30093(17) 0.3401(2) 0.60636(14) 0.0727(6) Uani 1 1 d . . . . .
O3 O 0.21368(14) 0.28802(15) 0.45126(13) 0.0546(5) Uani 1 1 d . . . . .
O4 O 0.4014(2) 0.9680(2) 0.3264(2) 0.1073(10) Uani 1 1 d . . . . .
O5 O 0.47754(17) 0.77666(19) 0.32832(16) 0.0745(6) Uani 1 1 d . . . . .
N1 N 0.18291(15) 0.48668(16) 0.49947(14) 0.0431(5) Uani 1 1 d . . . . .
C1 C 0.29372(19) 0.3322(2) 0.41720(16) 0.0428(5) Uani 1 1 d . . . . .
C2 C 0.3428(2) 0.2496(2) 0.37732(18) 0.0545(6) Uani 1 1 d . . . . .
H2 H 0.3213 0.1695 0.3721 0.065 Uiso 1 1 calc R U . . .
C3 C 0.4240(2) 0.2870(2) 0.34531(18) 0.0550(7) Uani 1 1 d . . . . .
H3 H 0.4558 0.2329 0.3158 0.066 Uiso 1 1 calc R U . . .
C4 C 0.4582(2) 0.4046(2) 0.35700(16) 0.0482(6) Uani 1 1 d . . . . .
H4 H 0.5162 0.4284 0.3388 0.058 Uiso 1 1 calc R U . . .
C5 C 0.40711(18) 0.4873(2) 0.39558(15) 0.0412(5) Uani 1 1 d . . . . .
H5 H 0.4312 0.5663 0.4033 0.049 Uiso 1 1 calc R U . . .
C6 C 0.31960(17) 0.45393(19) 0.42322(14) 0.0374(5) Uani 1 1 d . . . . .
C7 C 0.25630(16) 0.53889(19) 0.45804(14) 0.0345(4) Uani 1 1 d . . . . .
C8 C 0.24281(16) 0.65854(18) 0.45245(13) 0.0326(4) Uani 1 1 d . . . . .
C9 C 0.16196(17) 0.69657(18) 0.49898(14) 0.0355(5) Uani 1 1 d . . . . .
H9 H 0.0947 0.7128 0.4537 0.043 Uiso 1 1 calc R U . . .
C10 C 0.1494(2) 0.5821(2) 0.55047(17) 0.0474(6) Uani 1 1 d . . . . .
H10A H 0.1945 0.5848 0.6115 0.057 Uiso 1 1 calc R U . . .
H10B H 0.0767 0.5710 0.5506 0.057 Uiso 1 1 calc R U . . .
C11 C 0.28204(16) 0.74290(18) 0.39296(14) 0.0344(4) Uani 1 1 d . . . . .
H11 H 0.3042 0.6922 0.3505 0.041 Uiso 1 1 calc R U . . .
C12 C 0.38083(18) 0.8128(2) 0.44625(15) 0.0412(5) Uani 1 1 d . . . . .
H12A H 0.4258 0.7592 0.4899 0.049 Uiso 1 1 calc R U . . .
H12B H 0.3589 0.8776 0.4784 0.049 Uiso 1 1 calc R U . . .
C13 C 0.19159(18) 0.82123(19) 0.33835(14) 0.0375(5) Uani 1 1 d . . . . .
C14 C 0.1209(2) 0.7691(2) 0.26466(16) 0.0469(6) Uani 1 1 d . . . . .
H14 H 0.1312 0.6903 0.2490 0.056 Uiso 1 1 calc R U . . .
C15 C 0.0352(2) 0.8340(3) 0.2145(2) 0.0634(8) Uani 1 1 d . . . . .
H15 H -0.0129 0.7976 0.1661 0.076 Uiso 1 1 calc R U . . .
C16 C 0.0200(3) 0.9507(3) 0.2347(2) 0.0727(9) Uani 1 1 d . . . . .
H16 H -0.0372 0.9942 0.1999 0.087 Uiso 1 1 calc R U . . .
C17 C 0.0898(3) 1.0032(3) 0.3068(2) 0.0733(9) Uani 1 1 d . . . . .
H17 H 0.0798 1.0828 0.3209 0.088 Uiso 1 1 calc R U . . .
C18 C 0.1753(2) 0.9390(2) 0.35907(19) 0.0566(7) Uani 1 1 d . . . . .
H18 H 0.2220 0.9755 0.4083 0.068 Uiso 1 1 calc R U . . .
C19 C 0.19110(16) 0.80516(18) 0.55943(13) 0.0337(4) Uani 1 1 d . . . . .
C20 C 0.1209(2) 0.8981(2) 0.55480(16) 0.0489(6) Uani 1 1 d . . . . .
H20 H 0.0534 0.8934 0.5151 0.059 Uiso 1 1 calc R U . . .
C21 C 0.1498(2) 0.9983(2) 0.60853(18) 0.0591(7) Uani 1 1 d . . . . .
H21 H 0.1016 1.0606 0.6047 0.071 Uiso 1 1 calc R U . . .
C22 C 0.2489(2) 1.0066(2) 0.66745(17) 0.0546(6) Uani 1 1 d . . . . .
H22 H 0.2687 1.0750 0.7026 0.065 Uiso 1 1 calc R U . . .
C23 C 0.3184(2) 0.9139(2) 0.67422(16) 0.0471(6) Uani 1 1 d . . . . .
H23 H 0.3854 0.9187 0.7147 0.057 Uiso 1 1 calc R U . . .
C24 C 0.29002(18) 0.8127(2) 0.62134(14) 0.0398(5) Uani 1 1 d . . . . .
H24 H 0.3376 0.7493 0.6273 0.048 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4048(19) . ?
S1 O2 1.406(2) . ?
S1 O3 1.5891(19) . ?
S1 N1 1.6172(19) . ?
S2 O4 1.396(2) . ?
S2 O5 1.432(2) . ?
S2 F1 1.453(2) . ?
S2 C12 1.762(2) . ?
O3 C1 1.404(3) . ?
N1 C7 1.436(3) . ?
N1 C10 1.471(3) . ?
C1 C2 1.374(3) . ?
C1 C6 1.391(3) . ?
C2 C3 1.374(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.397(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.467(3) . ?
C7 C8 1.340(3) . ?
C8 C11 1.515(3) . ?
C8 C9 1.517(3) . ?
C9 C19 1.513(3) . ?
C9 C10 1.540(3) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C13 1.525(3) . ?
C11 C12 1.541(3) . ?
C11 H11 0.9800 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C18 1.380(3) . ?
C13 C14 1.385(3) . ?
C14 C15 1.380(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.364(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.365(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.387(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.375(3) . ?
C19 C24 1.387(3) . ?
C20 C21 1.382(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.370(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.363(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.383(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 120.20(14) . . ?
O1 S1 O3 106.37(12) . . ?
O2 S1 O3 109.02(12) . . ?
O1 S1 N1 108.23(11) . . ?
O2 S1 N1 113.16(12) . . ?
O3 S1 N1 97.18(10) . . ?
O4 S2 O5 112.26(18) . . ?
O4 S2 F1 112.70(19) . . ?
O5 S2 F1 108.07(15) . . ?
O4 S2 C12 111.68(13) . . ?
O5 S2 C12 106.40(12) . . ?
F1 S2 C12 105.28(12) . . ?
C1 O3 S1 115.62(15) . . ?
C7 N1 C10 107.66(17) . . ?
C7 N1 S1 118.98(15) . . ?
C10 N1 S1 120.24(16) . . ?
C2 C1 C6 122.7(2) . . ?
C2 C1 O3 116.5(2) . . ?
C6 C1 O3 120.7(2) . . ?
C3 C2 C1 119.1(2) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 119.9(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.9(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 116.5(2) . . ?
C1 C6 C7 119.7(2) . . ?
C5 C6 C7 123.8(2) . . ?
C8 C7 N1 109.61(18) . . ?
C8 C7 C6 133.9(2) . . ?
N1 C7 C6 116.15(18) . . ?
C7 C8 C11 126.21(19) . . ?
C7 C8 C9 110.08(18) . . ?
C11 C8 C9 122.51(17) . . ?
C19 C9 C8 115.85(17) . . ?
C19 C9 C10 112.08(18) . . ?
C8 C9 C10 102.67(17) . . ?
C19 C9 H9 108.6 . . ?
C8 C9 H9 108.6 . . ?
C10 C9 H9 108.6 . . ?
N1 C10 C9 102.42(17) . . ?
N1 C10 H10A 111.3 . . ?
C9 C10 H10A 111.3 . . ?
N1 C10 H10B 111.3 . . ?
C9 C10 H10B 111.3 . . ?
H10A C10 H10B 109.2 . . ?
C8 C11 C13 110.28(17) . . ?
C8 C11 C12 111.38(17) . . ?
C13 C11 C12 114.84(18) . . ?
C8 C11 H11 106.6 . . ?
C13 C11 H11 106.6 . . ?
C12 C11 H11 106.6 . . ?
C11 C12 S2 113.78(15) . . ?
C11 C12 H12A 108.8 . . ?
S2 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
S2 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C18 C13 C14 118.7(2) . . ?
C18 C13 C11 124.0(2) . . ?
C14 C13 C11 117.4(2) . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C14 121.0(3) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 119.3(3) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C16 C17 C18 120.7(3) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C13 C18 C17 120.3(3) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C20 C19 C24 118.4(2) . . ?
C20 C19 C9 121.3(2) . . ?
C24 C19 C9 120.26(18) . . ?
C19 C20 C21 120.6(2) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C22 C21 C20 120.4(2) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C23 C22 C21 119.5(2) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C22 C23 C24 120.5(2) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C23 C24 C19 120.4(2) . . ?
C23 C24 H24 119.8 . . ?
C19 C24 H24 119.8 . . ?

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
O1 S1 O3 C1 170.57(17) . . . . ?
O2 S1 O3 C1 -58.4(2) . . . . ?
N1 S1 O3 C1 59.12(18) . . . . ?
O1 S1 N1 C7 -164.17(18) . . . . ?
O2 S1 N1 C7 60.0(2) . . . . ?
O3 S1 N1 C7 -54.26(19) . . . . ?
O1 S1 N1 C10 59.4(2) . . . . ?
O2 S1 N1 C10 -76.4(2) . . . . ?
O3 S1 N1 C10 169.34(18) . . . . ?
S1 O3 C1 C2 145.7(2) . . . . ?
S1 O3 C1 C6 -35.2(3) . . . . ?
C6 C1 C2 C3 2.9(4) . . . . ?
O3 C1 C2 C3 -177.9(2) . . . . ?
C1 C2 C3 C4 2.9(4) . . . . ?
C2 C3 C4 C5 -4.2(4) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C2 C1 C6 C5 -7.1(3) . . . . ?
O3 C1 C6 C5 173.8(2) . . . . ?
C2 C1 C6 C7 173.4(2) . . . . ?
O3 C1 C6 C7 -5.7(3) . . . . ?
C4 C5 C6 C1 5.7(3) . . . . ?
C4 C5 C6 C7 -174.9(2) . . . . ?
C10 N1 C7 C8 -21.4(2) . . . . ?
S1 N1 C7 C8 -162.65(16) . . . . ?
C10 N1 C7 C6 164.85(19) . . . . ?
S1 N1 C7 C6 23.6(3) . . . . ?
C1 C6 C7 C8 -160.6(2) . . . . ?
C5 C6 C7 C8 20.0(4) . . . . ?
C1 C6 C7 N1 11.3(3) . . . . ?
C5 C6 C7 N1 -168.1(2) . . . . ?
N1 C7 C8 C11 -162.69(19) . . . . ?
C6 C7 C8 C11 9.6(4) . . . . ?
N1 C7 C8 C9 4.9(2) . . . . ?
C6 C7 C8 C9 177.2(2) . . . . ?
C7 C8 C9 C19 134.7(2) . . . . ?
C11 C8 C9 C19 -57.1(3) . . . . ?
C7 C8 C9 C10 12.2(2) . . . . ?
C11 C8 C9 C10 -179.61(19) . . . . ?
C7 N1 C10 C9 27.6(2) . . . . ?
S1 N1 C10 C9 168.36(16) . . . . ?
C19 C9 C10 N1 -148.55(18) . . . . ?
C8 C9 C10 N1 -23.6(2) . . . . ?
C7 C8 C11 C13 127.9(2) . . . . ?
C9 C8 C11 C13 -38.3(3) . . . . ?
C7 C8 C11 C12 -103.3(2) . . . . ?
C9 C8 C11 C12 90.5(2) . . . . ?
C8 C11 C12 S2 160.69(15) . . . . ?
C13 C11 C12 S2 -73.1(2) . . . . ?
O4 S2 C12 C11 69.2(2) . . . . ?
O5 S2 C12 C11 -53.7(2) . . . . ?
F1 S2 C12 C11 -168.21(19) . . . . ?
C8 C11 C13 C18 100.6(3) . . . . ?
C12 C11 C13 C18 -26.2(3) . . . . ?
C8 C11 C13 C14 -78.1(2) . . . . ?
C12 C11 C13 C14 155.1(2) . . . . ?
C18 C13 C14 C15 -1.1(4) . . . . ?
C11 C13 C14 C15 177.6(2) . . . . ?
C13 C14 C15 C16 1.8(4) . . . . ?
C14 C15 C16 C17 -1.2(5) . . . . ?
C15 C16 C17 C18 0.0(5) . . . . ?
C14 C13 C18 C17 0.0(4) . . . . ?
C11 C13 C18 C17 -178.7(2) . . . . ?
C16 C17 C18 C13 0.6(5) . . . . ?
C8 C9 C19 C20 132.0(2) . . . . ?
C10 C9 C19 C20 -110.6(2) . . . . ?
C8 C9 C19 C24 -48.2(3) . . . . ?
C10 C9 C19 C24 69.2(2) . . . . ?
C24 C19 C20 C21 2.2(4) . . . . ?
C9 C19 C20 C21 -178.0(2) . . . . ?
C19 C20 C21 C22 -0.1(4) . . . . ?
C20 C21 C22 C23 -1.5(4) . . . . ?
C21 C22 C23 C24 0.9(4) . . . . ?
C22 C23 C24 C19 1.2(4) . . . . ?
C20 C19 C24 C23 -2.8(3) . . . . ?
C9 C19 C24 C23 177.4(2) . . . . ?

_refine_diff_density_max         0.335
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.056

