# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1961173'
loop_
_audit_author_name
_audit_author_address
'Feng Li'
;Shangqiu Normal University
China
;
_audit_update_record             
;
2019-10-24 deposited with the CCDC.	2021-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H15 N O4 S'
_chemical_formula_weight         329.36

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.8457(8)
_cell_length_b                   8.1317(9)
_cell_length_c                   16.630(2)
_cell_angle_alpha                102.410(4)
_cell_angle_beta                 91.559(5)
_cell_angle_gamma                99.457(5)
_cell_volume                     759.95(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6235
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      27.44

_exptl_crystal_description       block
_exptl_crystal_colour            color
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6818
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Sheldrick,1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11510
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0175
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.13
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2641
_reflns_number_gt                2284
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0466P)²+0.2215P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2641
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0947
_refine_ls_wR_factor_gt          0.0904
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.56302(8) 0.27993(5) 0.84674(3) 0.05064(17) Uani 1 1 d . . .
N1 N 0.4541(3) 0.38390(17) 0.78656(8) 0.0475(4) Uani 1 1 d . . .
O1 O -0.2039(2) 0.3707(2) 0.60118(10) 0.0789(5) Uani 1 1 d . . .
O3 O 0.5598(3) 0.11013(17) 0.80343(10) 0.0795(5) Uani 1 1 d . . .
O4 O 0.4589(2) 0.30832(18) 0.92313(8) 0.0649(4) Uani 1 1 d . . .
O5 O 0.8318(2) 0.36070(15) 0.86222(8) 0.0561(3) Uani 1 1 d . . .
C1 C -0.0683(4) -0.0099(3) 0.33663(13) 0.0625(5) Uani 1 1 d . . .
H1 H -0.0796 -0.0883 0.2863 0.075 Uiso 1 1 calc R . .
C2 C 0.1401(4) 0.0907(2) 0.36653(12) 0.0577(5) Uani 1 1 d . . .
H13 H 0.2708 0.0802 0.3365 0.069 Uiso 1 1 calc R . .
C3 C 0.1584(3) 0.2078(2) 0.44101(11) 0.0507(4) Uani 1 1 d . . .
H14 H 0.3011 0.2761 0.4606 0.061 Uiso 1 1 calc R . .
C4 C -0.0350(3) 0.2245(2) 0.48686(10) 0.0435(4) Uani 1 1 d . . .
C5 C -0.0248(3) 0.3458(2) 0.56828(12) 0.0477(4) Uani 1 1 d . . .
C6 C 0.2079(3) 0.4360(2) 0.60968(10) 0.0447(4) Uani 1 1 d . . .
H5 H 0.3030 0.3512 0.6150 0.054 Uiso 1 1 calc R . .
H4 H 0.2851 0.5066 0.5749 0.054 Uiso 1 1 calc R . .
C7 C 0.1917(3) 0.5464(2) 0.69365(11) 0.0511(4) Uani 1 1 d . . .
H12 H 0.1117 0.4759 0.7280 0.061 Uiso 1 1 calc R . .
H6 H 0.0983 0.6320 0.6881 0.061 Uiso 1 1 calc R . .
C8 C 0.4249(3) 0.6363(2) 0.73707(11) 0.0504(4) Uani 1 1 d . . .
H7 H 0.5291 0.6630 0.6955 0.060 Uiso 1 1 calc R . .
H8 H 0.4030 0.7440 0.7718 0.060 Uiso 1 1 calc R . .
C9 C 0.5435(3) 0.5418(2) 0.78937(9) 0.0414(4) Uani 1 1 d . . .
C10 C 0.7536(3) 0.6308(2) 0.84045(9) 0.0423(4) Uani 1 1 d . . .
C11 C 0.8916(3) 0.5389(2) 0.87667(10) 0.0454(4) Uani 1 1 d . . .
C12 C 1.0967(3) 0.6130(3) 0.92231(11) 0.0558(5) Uani 1 1 d . . .
H9 H 1.1850 0.5474 0.9453 0.067 Uiso 1 1 calc R . .
C13 C 1.1679(4) 0.7866(3) 0.93303(12) 0.0642(5) Uani 1 1 d . . .
H2 H 1.3059 0.8393 0.9637 0.077 Uiso 1 1 calc R . .
C14 C -0.2616(4) 0.0049(3) 0.38125(14) 0.0654(5) Uani 1 1 d . . .
H3 H -0.4037 -0.0635 0.3611 0.078 Uiso 1 1 calc R . .
C15 C -0.2450(3) 0.1207(2) 0.45556(13) 0.0550(5) Uani 1 1 d . . .
H15 H -0.3764 0.1296 0.4854 0.066 Uiso 1 1 calc R . .
C16 C 1.0359(4) 0.8835(3) 0.89855(13) 0.0653(5) Uani 1 1 d . . .
H11 H 1.0852 1.0008 0.9064 0.078 Uiso 1 1 calc R . .
C17 C 0.8318(3) 0.8070(2) 0.85265(11) 0.0544(5) Uani 1 1 d . . .
H10 H 0.7450 0.8732 0.8295 0.065 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.4103(14) . ?
S1 O4 1.4141(14) . ?
S1 O5 1.5913(14) . ?
S1 N1 1.6208(14) . ?
N1 C9 1.295(2) . ?
O1 C5 1.221(2) . ?
O5 C11 1.400(2) . ?
C1 C2 1.366(3) . ?
C1 C14 1.376(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.380(3) . ?
C2 H13 0.9300 . ?
C3 C4 1.390(2) . ?
C3 H14 0.9300 . ?
C4 C15 1.387(2) . ?
C4 C5 1.487(3) . ?
C5 C6 1.506(2) . ?
C6 C7 1.504(2) . ?
C6 H5 0.9700 . ?
C6 H4 0.9700 . ?
C7 C8 1.519(3) . ?
C7 H12 0.9700 . ?
C7 H6 0.9700 . ?
C8 C9 1.502(2) . ?
C8 H7 0.9700 . ?
C8 H8 0.9700 . ?
C9 C10 1.463(2) . ?
C10 C11 1.392(2) . ?
C10 C17 1.399(2) . ?
C11 C12 1.376(3) . ?
C12 C13 1.375(3) . ?
C12 H9 0.9300 . ?
C13 C16 1.384(3) . ?
C13 H2 0.9300 . ?
C14 C15 1.373(3) . ?
C14 H3 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.377(3) . ?
C16 H11 0.9300 . ?
C17 H10 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O4 118.72(10) . . ?
O3 S1 O5 104.29(9) . . ?
O4 S1 O5 108.49(8) . . ?
O3 S1 N1 109.31(8) . . ?
O4 S1 N1 109.25(8) . . ?
O5 S1 N1 105.99(7) . . ?
C9 N1 S1 120.06(12) . . ?
C11 O5 S1 117.38(10) . . ?
C2 C1 C14 119.8(2) . . ?
C2 C1 H1 120.1 . . ?
C14 C1 H1 120.1 . . ?
C1 C2 C3 120.55(19) . . ?
C1 C2 H13 119.7 . . ?
C3 C2 H13 119.7 . . ?
C2 C3 C4 120.40(17) . . ?
C2 C3 H14 119.8 . . ?
C4 C3 H14 119.8 . . ?
C3 C4 C15 118.17(17) . . ?
C3 C4 C5 122.80(16) . . ?
C15 C4 C5 119.03(16) . . ?
O1 C5 C4 120.04(17) . . ?
O1 C5 C6 120.57(17) . . ?
C4 C5 C6 119.38(14) . . ?
C7 C6 C5 113.39(14) . . ?
C7 C6 H5 108.9 . . ?
C5 C6 H5 108.9 . . ?
C7 C6 H4 108.9 . . ?
C5 C6 H4 108.9 . . ?
H5 C6 H4 107.7 . . ?
C6 C7 C8 114.22(14) . . ?
C6 C7 H12 108.7 . . ?
C8 C7 H12 108.7 . . ?
C6 C7 H6 108.7 . . ?
C8 C7 H6 108.7 . . ?
H12 C7 H6 107.6 . . ?
C9 C8 C7 117.05(15) . . ?
C9 C8 H7 108.0 . . ?
C7 C8 H7 108.0 . . ?
C9 C8 H8 108.0 . . ?
C7 C8 H8 108.0 . . ?
H7 C8 H8 107.3 . . ?
N1 C9 C10 123.05(14) . . ?
N1 C9 C8 117.89(15) . . ?
C10 C9 C8 119.06(14) . . ?
C11 C10 C17 116.81(16) . . ?
C11 C10 C9 120.09(15) . . ?
C17 C10 C9 123.04(15) . . ?
C12 C11 C10 123.19(17) . . ?
C12 C11 O5 116.95(15) . . ?
C10 C11 O5 119.70(15) . . ?
C13 C12 C11 118.34(18) . . ?
C13 C12 H9 120.8 . . ?
C11 C12 H9 120.8 . . ?
C12 C13 C16 120.55(19) . . ?
C12 C13 H2 119.7 . . ?
C16 C13 H2 119.7 . . ?
C15 C14 C1 120.08(18) . . ?
C15 C14 H3 120.0 . . ?
C1 C14 H3 120.0 . . ?
C14 C15 C4 121.01(18) . . ?
C14 C15 H15 119.5 . . ?
C4 C15 H15 119.5 . . ?
C17 C16 C13 120.32(19) . . ?
C17 C16 H11 119.8 . . ?
C13 C16 H11 119.8 . . ?
C16 C17 C10 120.78(18) . . ?
C16 C17 H10 119.6 . . ?
C10 C17 H10 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 S1 N1 C9 -141.59(15) . . . . ?
O4 S1 N1 C9 86.99(15) . . . . ?
O5 S1 N1 C9 -29.72(15) . . . . ?
O3 S1 O5 C11 157.56(12) . . . . ?
O4 S1 O5 C11 -75.00(13) . . . . ?
N1 S1 O5 C11 42.22(13) . . . . ?
C14 C1 C2 C3 -0.3(3) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C3 C4 C15 -0.1(3) . . . . ?
C2 C3 C4 C5 178.69(16) . . . . ?
C3 C4 C5 O1 170.93(17) . . . . ?
C15 C4 C5 O1 -10.3(3) . . . . ?
C3 C4 C5 C6 -9.5(2) . . . . ?
C15 C4 C5 C6 169.26(15) . . . . ?
O1 C5 C6 C7 3.0(2) . . . . ?
C4 C5 C6 C7 -176.61(14) . . . . ?
C5 C6 C7 C8 179.04(14) . . . . ?
C6 C7 C8 C9 -88.81(19) . . . . ?
S1 N1 C9 C10 5.0(2) . . . . ?
S1 N1 C9 C8 -175.39(12) . . . . ?
C7 C8 C9 N1 7.9(2) . . . . ?
C7 C8 C9 C10 -172.48(14) . . . . ?
N1 C9 C10 C11 12.2(2) . . . . ?
C8 C9 C10 C11 -167.47(14) . . . . ?
N1 C9 C10 C17 -170.70(16) . . . . ?
C8 C9 C10 C17 9.7(2) . . . . ?
C17 C10 C11 C12 -0.3(2) . . . . ?
C9 C10 C11 C12 176.98(15) . . . . ?
C17 C10 C11 O5 -175.63(15) . . . . ?
C9 C10 C11 O5 1.7(2) . . . . ?
S1 O5 C11 C12 153.60(13) . . . . ?
S1 O5 C11 C10 -30.81(19) . . . . ?
C10 C11 C12 C13 0.4(3) . . . . ?
O5 C11 C12 C13 175.83(16) . . . . ?
C11 C12 C13 C16 -0.1(3) . . . . ?
C2 C1 C14 C15 0.0(3) . . . . ?
C1 C14 C15 C4 0.2(3) . . . . ?
C3 C4 C15 C14 -0.2(3) . . . . ?
C5 C4 C15 C14 -178.97(16) . . . . ?
C12 C13 C16 C17 -0.3(3) . . . . ?
C13 C16 C17 C10 0.4(3) . . . . ?
C11 C10 C17 C16 -0.1(3) . . . . ?
C9 C10 C17 C16 -177.31(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.031
####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1972915'
loop_
_audit_author_name
_audit_author_address
'Feng Li'
;Shangqiu Normal University
China
;
_audit_update_record             
;
2019-12-19 deposited with the CCDC.	2021-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H13 N O4 S'
_chemical_formula_weight         315.33

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   16.556(2)
_cell_length_b                   5.6598(7)
_cell_length_c                   17.572(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.833(4)
_cell_angle_gamma                90.00
_cell_volume                     1482.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    3896
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5571
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Sheldrick,1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20112
_diffrn_reflns_av_R_equivalents  0.1068
_diffrn_reflns_av_sigmaI/netI    0.0538
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.49
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2597
_reflns_number_gt                1622
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0563P)²+0.4684P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2597
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1062
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.1332
_refine_ls_wR_factor_gt          0.1191
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.81756(6) 0.12515(19) 0.46152(5) 0.0594(3) Uani 1 1 d . . .
O1 O 0.74763(16) 0.0002(4) 0.37630(14) 0.0612(6) Uani 1 1 d . . .
O2 O 0.84754(19) -0.0616(5) 0.52012(15) 0.0886(9) Uani 1 1 d . . .
O3 O 0.87978(16) 0.2563(5) 0.44347(16) 0.0807(8) Uani 1 1 d . . .
O4 O 0.57726(18) 0.1989(5) 0.50430(15) 0.0880(10) Uani 1 1 d . . .
N1 N 0.75629(17) 0.3044(5) 0.48672(15) 0.0504(7) Uani 1 1 d . . .
C1 C 0.6166(2) 0.2025(7) 0.8005(2) 0.0567(9) Uani 1 1 d . . .
H1 H 0.6167 0.1715 0.8525 0.068 Uiso 1 1 calc R . .
C2 C 0.5753(2) 0.0473(6) 0.7343(2) 0.0551(9) Uani 1 1 d . . .
H13 H 0.5479 -0.0887 0.7415 0.066 Uiso 1 1 calc R . .
C3 C 0.5752(2) 0.0954(6) 0.6574(2) 0.0500(8) Uani 1 1 d . . .
H12 H 0.5469 -0.0086 0.6125 0.060 Uiso 1 1 calc R . .
C4 C 0.61616(18) 0.2954(6) 0.64584(17) 0.0417(8) Uani 1 1 d . . .
C5 C 0.61271(19) 0.3422(6) 0.56085(19) 0.0488(8) Uani 1 1 d . . .
C6 C 0.6526(2) 0.5629(6) 0.54530(19) 0.0535(9) Uani 1 1 d . . .
H9 H 0.7165 0.5649 0.5823 0.064 Uiso 1 1 calc R . .
H3 H 0.6258 0.6984 0.5593 0.064 Uiso 1 1 calc R . .
C7 C 0.6386(2) 0.5845(6) 0.4547(2) 0.0565(9) Uani 1 1 d . . .
H4 H 0.5749 0.5711 0.4179 0.068 Uiso 1 1 calc R . .
H5 H 0.6576 0.7408 0.4465 0.068 Uiso 1 1 calc R . .
C8 C 0.68744(19) 0.4054(5) 0.42809(18) 0.0415(7) Uani 1 1 d . . .
C9 C 0.65662(19) 0.3500(6) 0.33823(17) 0.0422(7) Uani 1 1 d . . .
C10 C 0.5933(2) 0.4878(6) 0.27362(19) 0.0541(9) Uani 1 1 d . . .
H8 H 0.5712 0.6245 0.2872 0.065 Uiso 1 1 calc R . .
C11 C 0.5635(2) 0.4232(7) 0.1906(2) 0.0640(10) Uani 1 1 d . . .
H7 H 0.5223 0.5179 0.1482 0.077 Uiso 1 1 calc R . .
C12 C 0.5942(2) 0.2194(8) 0.1699(2) 0.0661(11) Uani 1 1 d . . .
H2 H 0.5726 0.1751 0.1134 0.079 Uiso 1 1 calc R . .
C13 C 0.6868(2) 0.1492(6) 0.31431(19) 0.0476(8) Uani 1 1 d . . .
C14 C 0.6567(2) 0.0797(7) 0.2318(2) 0.0607(10) Uani 1 1 d . . .
H6 H 0.6779 -0.0580 0.2179 0.073 Uiso 1 1 calc R . .
C15 C 0.6578(2) 0.4495(6) 0.71329(18) 0.0474(8) Uani 1 1 d . . .
H11 H 0.6860 0.5849 0.7067 0.057 Uiso 1 1 calc R . .
C16 C 0.6573(2) 0.4009(6) 0.79033(19) 0.0539(9) Uani 1 1 d . . .
H10 H 0.6850 0.5045 0.8354 0.065 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.406(3) . ?
S1 O3 1.413(3) . ?
S1 O1 1.604(2) . ?
S1 N1 1.627(3) . ?
O1 C13 1.398(4) . ?
O4 C5 1.217(3) . ?
N1 C8 1.290(4) . ?
C1 C16 1.361(5) . ?
C1 C2 1.378(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.379(4) . ?
C2 H13 0.9300 . ?
C3 C4 1.379(4) . ?
C3 H12 0.9300 . ?
C4 C15 1.389(4) . ?
C4 C5 1.493(4) . ?
C5 C6 1.493(5) . ?
C6 C7 1.511(4) . ?
C6 H9 0.9700 . ?
C6 H3 0.9700 . ?
C7 C8 1.493(4) . ?
C7 H4 0.9700 . ?
C7 H5 0.9700 . ?
C8 C9 1.466(4) . ?
C9 C13 1.379(4) . ?
C9 C10 1.400(4) . ?
C10 C11 1.370(4) . ?
C10 H8 0.9300 . ?
C11 C12 1.373(5) . ?
C11 H7 0.9300 . ?
C12 C14 1.378(5) . ?
C12 H2 0.9300 . ?
C13 C14 1.370(4) . ?
C14 H6 0.9300 . ?
C15 C16 1.385(4) . ?
C15 H11 0.9300 . ?
C16 H10 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O3 119.99(18) . . ?
O2 S1 O1 103.49(17) . . ?
O3 S1 O1 108.80(15) . . ?
O2 S1 N1 109.41(15) . . ?
O3 S1 N1 109.60(17) . . ?
O1 S1 N1 104.30(13) . . ?
C13 O1 S1 116.3(2) . . ?
C8 N1 S1 119.9(2) . . ?
C16 C1 C2 120.4(3) . . ?
C16 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C1 C2 C3 119.4(3) . . ?
C1 C2 H13 120.3 . . ?
C3 C2 H13 120.3 . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H12 119.5 . . ?
C4 C3 H12 119.5 . . ?
C3 C4 C15 118.9(3) . . ?
C3 C4 C5 119.0(3) . . ?
C15 C4 C5 122.0(3) . . ?
O4 C5 C4 119.5(3) . . ?
O4 C5 C6 120.2(3) . . ?
C4 C5 C6 120.3(3) . . ?
C5 C6 C7 112.5(3) . . ?
C5 C6 H9 109.1 . . ?
C7 C6 H9 109.1 . . ?
C5 C6 H3 109.1 . . ?
C7 C6 H3 109.1 . . ?
H9 C6 H3 107.8 . . ?
C8 C7 C6 114.8(3) . . ?
C8 C7 H4 108.6 . . ?
C6 C7 H4 108.6 . . ?
C8 C7 H5 108.6 . . ?
C6 C7 H5 108.6 . . ?
H4 C7 H5 107.5 . . ?
N1 C8 C9 122.5(3) . . ?
N1 C8 C7 117.5(3) . . ?
C9 C8 C7 120.0(3) . . ?
C13 C9 C10 117.1(3) . . ?
C13 C9 C8 120.2(3) . . ?
C10 C9 C8 122.7(3) . . ?
C11 C10 C9 120.7(3) . . ?
C11 C10 H8 119.7 . . ?
C9 C10 H8 119.7 . . ?
C10 C11 C12 120.3(3) . . ?
C10 C11 H7 119.9 . . ?
C12 C11 H7 119.9 . . ?
C11 C12 C14 120.7(3) . . ?
C11 C12 H2 119.7 . . ?
C14 C12 H2 119.7 . . ?
C14 C13 C9 123.1(3) . . ?
C14 C13 O1 117.3(3) . . ?
C9 C13 O1 119.5(3) . . ?
C13 C14 C12 118.2(3) . . ?
C13 C14 H6 120.9 . . ?
C12 C14 H6 120.9 . . ?
C16 C15 C4 119.8(3) . . ?
C16 C15 H11 120.1 . . ?
C4 C15 H11 120.1 . . ?
C1 C16 C15 120.4(3) . . ?
C1 C16 H10 119.8 . . ?
C15 C16 H10 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
O2 S1 O1 C13 161.1(2) . . . . ?
O3 S1 O1 C13 -70.2(2) . . . . ?
N1 S1 O1 C13 46.7(2) . . . . ?
O2 S1 N1 C8 -143.7(3) . . . . ?
O3 S1 N1 C8 82.8(3) . . . . ?
O1 S1 N1 C8 -33.5(3) . . . . ?
C16 C1 C2 C3 -0.4(5) . . . . ?
C1 C2 C3 C4 0.5(5) . . . . ?
C2 C3 C4 C15 -0.2(5) . . . . ?
C2 C3 C4 C5 -178.9(3) . . . . ?
C3 C4 C5 O4 -3.1(5) . . . . ?
C15 C4 C5 O4 178.3(3) . . . . ?
C3 C4 C5 C6 177.1(3) . . . . ?
C15 C4 C5 C6 -1.6(4) . . . . ?
O4 C5 C6 C7 2.9(5) . . . . ?
C4 C5 C6 C7 -177.2(3) . . . . ?
C5 C6 C7 C8 -66.9(4) . . . . ?
S1 N1 C8 C9 5.5(4) . . . . ?
S1 N1 C8 C7 -174.6(2) . . . . ?
C6 C7 C8 N1 -21.8(4) . . . . ?
C6 C7 C8 C9 158.1(3) . . . . ?
N1 C8 C9 C13 15.4(4) . . . . ?
C7 C8 C9 C13 -164.5(3) . . . . ?
N1 C8 C9 C10 -167.7(3) . . . . ?
C7 C8 C9 C10 12.4(4) . . . . ?
C13 C9 C10 C11 -0.1(4) . . . . ?
C8 C9 C10 C11 -177.1(3) . . . . ?
C9 C10 C11 C12 1.3(5) . . . . ?
C10 C11 C12 C14 -1.4(5) . . . . ?
C10 C9 C13 C14 -1.1(5) . . . . ?
C8 C9 C13 C14 176.0(3) . . . . ?
C10 C9 C13 O1 -177.6(3) . . . . ?
C8 C9 C13 O1 -0.6(4) . . . . ?
S1 O1 C13 C14 150.5(2) . . . . ?
S1 O1 C13 C9 -32.7(4) . . . . ?
C9 C13 C14 C12 0.9(5) . . . . ?
O1 C13 C14 C12 177.6(3) . . . . ?
C11 C12 C14 C13 0.3(5) . . . . ?
C3 C4 C15 C16 -0.2(4) . . . . ?
C5 C4 C15 C16 178.4(3) . . . . ?
C2 C1 C16 C15 0.0(5) . . . . ?
C4 C15 C16 C1 0.3(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.049
