# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_d
_database_code_depnum_ccdc_archive 'CCDC 1444603'
_audit_update_record             
;
2015-12-29 deposited with the CCDC.
2016-03-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H7.50 N0.50 O1.50 S'
_chemical_formula_weight         166.70

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           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

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

_cell_length_a                   8.6713(17)
_cell_length_b                   9.4094(19)
_cell_length_c                   11.261(2)
_cell_angle_alpha                104.56(3)
_cell_angle_beta                 93.63(3)
_cell_angle_gamma                110.49(3)
_cell_volume                     821.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    818
_cell_measurement_theta_min      2.5398
_cell_measurement_theta_max      27.4179

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
_exptl_absorpt_coefficient_mu    0.335
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6408
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0353
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.54
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3752
_reflns_number_gt                2722
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0980P)²+0.3825P] 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         3752
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0660
_refine_ls_wR_factor_ref         0.2005
_refine_ls_wR_factor_gt          0.1813
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.074
_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 0.52027(13) 0.71941(14) 0.44162(11) 0.0794(4) Uani 1 1 d . . .
N1 N 0.1260(3) 0.6110(3) 0.3837(2) 0.0461(6) Uani 1 1 d . . .
H1D H 0.1389 0.6371 0.4636 0.055 Uiso 1 1 calc R . .
O1 O 0.0280(3) 0.3393(3) 0.3944(2) 0.0628(6) Uani 1 1 d . . .
C1 C 0.7305(5) 0.8193(5) 0.4621(4) 0.0794(12) Uani 1 1 d . . .
H1A H 0.8073 0.7916 0.5028 0.095 Uiso 1 1 calc R . .
S2 S 0.05970(10) 0.42520(9) 0.30323(7) 0.0491(3) Uani 1 1 d . . .
O2 O 0.1760(3) 0.4065(3) 0.2228(2) 0.0624(6) Uani 1 1 d . . .
C2 C 0.7745(5) 0.9407(5) 0.4145(4) 0.0771(11) Uani 1 1 d . . .
H2A H 0.8857 1.0045 0.4192 0.093 Uiso 1 1 calc R . .
O3 O 0.3080(3) 0.9316(2) 0.2555(2) 0.0539(5) Uani 1 1 d . . .
C3 C 0.6383(3) 0.9674(4) 0.3546(3) 0.0607(8) Uani 1 1 d U . .
H3A H 0.6469 1.0473 0.3177 0.073 Uiso 1 1 calc R . .
C4 C 0.4861(4) 0.8445(4) 0.3641(3) 0.0497(6) Uani 1 1 d U . .
C5 C 0.3195(4) 0.8273(3) 0.3182(3) 0.0435(6) Uani 1 1 d . . .
C6 C 0.1624(3) 0.7299(3) 0.3217(2) 0.0415(6) Uani 1 1 d . . .
C7 C 0.0484(4) 0.7754(3) 0.2590(3) 0.0495(7) Uani 1 1 d . . .
H7A H -0.0675 0.7294 0.2468 0.059 Uiso 1 1 calc R . .
C8 C 0.1403(4) 0.8968(4) 0.2210(3) 0.0564(8) Uani 1 1 d . . .
C9 C 0.1000(6) 0.9986(5) 0.1516(5) 0.0920(14) Uani 1 1 d . . .
H9A H -0.0190 0.9653 0.1319 0.138 Uiso 1 1 calc R . .
H9B H 0.1462 0.9888 0.0761 0.138 Uiso 1 1 calc R . .
H9C H 0.1468 1.1073 0.2021 0.138 Uiso 1 1 calc R . .
C11 C -0.1314(4) 0.3798(3) 0.2109(3) 0.0487(7) Uani 1 1 d . . .
C12 C -0.2722(4) 0.3691(5) 0.2639(3) 0.0666(9) Uani 1 1 d . . .
H12A H -0.2672 0.3811 0.3487 0.080 Uiso 1 1 calc R . .
C13 C -0.4204(5) 0.3406(5) 0.1920(3) 0.0752(11) Uani 1 1 d . . .
H13A H -0.5145 0.3339 0.2291 0.090 Uiso 1 1 calc R . .
C14 C -0.4317(5) 0.3215(5) 0.0651(3) 0.0717(10) Uani 1 1 d . . .
C15 C -0.2864(5) 0.3378(5) 0.0139(3) 0.0792(11) Uani 1 1 d . . .
H15A H -0.2900 0.3297 -0.0703 0.095 Uiso 1 1 calc R . .
C16 C -0.1380(5) 0.3655(5) 0.0846(3) 0.0667(9) Uani 1 1 d . . .
H16A H -0.0429 0.3746 0.0483 0.080 Uiso 1 1 calc R . .
C17 C -0.5936(6) 0.2842(7) -0.0146(4) 0.1060(17) Uani 1 1 d . . .
H17A H -0.6796 0.2769 0.0359 0.159 Uiso 1 1 calc R . .
H17B H -0.6225 0.1849 -0.0778 0.159 Uiso 1 1 calc R . .
H17C H -0.5826 0.3667 -0.0529 0.159 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 C1 1.702(4) . ?
S1 C4 1.722(3) . ?
N1 C6 1.418(3) . ?
N1 S2 1.625(3) . ?
O1 S2 1.443(2) . ?
C1 C2 1.329(6) . ?
S2 O2 1.424(2) . ?
S2 C11 1.753(3) . ?
C2 C3 1.450(5) . ?
O3 C5 1.371(3) . ?
O3 C8 1.380(4) . ?
C3 C4 1.450(5) . ?
C4 C5 1.442(4) . ?
C5 C6 1.360(4) . ?
C6 C7 1.421(4) . ?
C7 C8 1.332(4) . ?
C8 C9 1.493(4) . ?
C11 C12 1.376(4) . ?
C11 C16 1.390(4) . ?
C12 C13 1.377(5) . ?
C13 C14 1.388(5) . ?
C14 C15 1.394(6) . ?
C14 C17 1.495(6) . ?
C15 C16 1.375(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C4 90.9(2) . . ?
C6 N1 S2 119.82(19) . . ?
C2 C1 S1 113.7(3) . . ?
O2 S2 O1 119.68(14) . . ?
O2 S2 N1 108.06(14) . . ?
O1 S2 N1 104.79(14) . . ?
O2 S2 C11 108.13(15) . . ?
O1 S2 C11 108.17(15) . . ?
N1 S2 C11 107.43(13) . . ?
C1 C2 C3 115.8(4) . . ?
C5 O3 C8 107.2(2) . . ?
C4 C3 C2 106.1(3) . . ?
C5 C4 C3 125.0(3) . . ?
C5 C4 S1 121.5(2) . . ?
C3 C4 S1 113.5(2) . . ?
C6 C5 O3 108.4(2) . . ?
C6 C5 C4 135.4(3) . . ?
O3 C5 C4 116.2(3) . . ?
C5 C6 N1 124.1(2) . . ?
C5 C6 C7 107.7(3) . . ?
N1 C6 C7 128.1(3) . . ?
C8 C7 C6 106.5(3) . . ?
C7 C8 O3 110.3(2) . . ?
C7 C8 C9 134.0(3) . . ?
O3 C8 C9 115.8(3) . . ?
C12 C11 C16 119.7(3) . . ?
C12 C11 S2 120.5(2) . . ?
C16 C11 S2 119.6(3) . . ?
C11 C12 C13 120.4(3) . . ?
C12 C13 C14 121.1(4) . . ?
C13 C14 C15 117.6(4) . . ?
C13 C14 C17 121.4(4) . . ?
C15 C14 C17 120.9(4) . . ?
C16 C15 C14 121.8(3) . . ?
C15 C16 C11 119.3(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 S1 C1 C2 0.3(4) . . . . ?
C6 N1 S2 O2 54.1(2) . . . . ?
C6 N1 S2 O1 -177.2(2) . . . . ?
C6 N1 S2 C11 -62.3(2) . . . . ?
S1 C1 C2 C3 0.3(5) . . . . ?
C1 C2 C3 C4 -0.8(5) . . . . ?
C2 C3 C4 C5 179.1(3) . . . . ?
C2 C3 C4 S1 1.0(3) . . . . ?
C1 S1 C4 C5 -178.9(3) . . . . ?
C1 S1 C4 C3 -0.8(3) . . . . ?
C8 O3 C5 C6 0.3(3) . . . . ?
C8 O3 C5 C4 -179.3(3) . . . . ?
C3 C4 C5 C6 -176.0(3) . . . . ?
S1 C4 C5 C6 2.0(5) . . . . ?
C3 C4 C5 O3 3.5(4) . . . . ?
S1 C4 C5 O3 -178.6(2) . . . . ?
O3 C5 C6 N1 -177.3(2) . . . . ?
C4 C5 C6 N1 2.2(5) . . . . ?
O3 C5 C6 C7 -0.1(3) . . . . ?
C4 C5 C6 C7 179.4(3) . . . . ?
S2 N1 C6 C5 -106.4(3) . . . . ?
S2 N1 C6 C7 77.0(3) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
N1 C6 C7 C8 176.9(3) . . . . ?
C6 C7 C8 O3 0.3(4) . . . . ?
C6 C7 C8 C9 -179.7(4) . . . . ?
C5 O3 C8 C7 -0.3(4) . . . . ?
C5 O3 C8 C9 179.6(3) . . . . ?
O2 S2 C11 C12 171.9(3) . . . . ?
O1 S2 C11 C12 41.0(3) . . . . ?
N1 S2 C11 C12 -71.7(3) . . . . ?
O2 S2 C11 C16 -12.5(3) . . . . ?
O1 S2 C11 C16 -143.5(3) . . . . ?
N1 S2 C11 C16 103.9(3) . . . . ?
C16 C11 C12 C13 1.5(6) . . . . ?
S2 C11 C12 C13 177.0(3) . . . . ?
C11 C12 C13 C14 0.2(6) . . . . ?
C12 C13 C14 C15 -2.2(7) . . . . ?
C12 C13 C14 C17 177.5(4) . . . . ?
C13 C14 C15 C16 2.5(7) . . . . ?
C17 C14 C15 C16 -177.2(4) . . . . ?
C14 C15 C16 C11 -0.9(7) . . . . ?
C12 C11 C16 C15 -1.2(6) . . . . ?
S2 C11 C16 C15 -176.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.650
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.064
####################################################################### 
# 
# 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_d
_database_code_depnum_ccdc_archive 'CCDC 1444604'
_audit_update_record             
;
2015-12-29 deposited with the CCDC.
2016-03-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H23 N O4 S'
_chemical_formula_weight         433.50

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                   14.818(3)
_cell_length_b                   10.636(2)
_cell_length_c                   15.416(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.84(3)
_cell_angle_gamma                90.00
_cell_volume                     2222.3(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    1596
_cell_measurement_theta_min      2.3924
_cell_measurement_theta_max      27.3717

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17014
_diffrn_reflns_av_R_equivalents  0.0688
_diffrn_reflns_av_sigmaI/netI    0.0642
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         27.48
_reflns_number_total             5092
_reflns_number_gt                3190
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0902P)²+0.0000P] 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         5092
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1252
_refine_ls_R_factor_gt           0.0765
_refine_ls_wR_factor_ref         0.2036
_refine_ls_wR_factor_gt          0.1750
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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 0.40589(6) 0.13835(7) 0.03933(5) 0.0486(3) Uani 1 1 d . . .
N1 N 0.51447(18) 0.1038(2) 0.11906(15) 0.0481(6) Uani 1 1 d . . .
H1D H 0.5543 0.0622 0.1018 0.058 Uiso 1 1 calc R . .
O1 O 0.61893(15) 0.24095(18) 0.35098(13) 0.0493(5) Uani 1 1 d . . .
O2 O 0.3484(2) -0.4077(2) 0.23289(19) 0.0795(8) Uani 1 1 d . . .
O3 O 0.41339(17) 0.11665(19) -0.04945(13) 0.0562(6) Uani 1 1 d . . .
O4 O 0.38020(17) 0.26045(18) 0.06056(15) 0.0590(6) Uani 1 1 d . . .
C1 C 0.6163(3) 0.0977(3) 0.4723(2) 0.0636(9) Uani 1 1 d . . .
H1A H 0.5910 0.0165 0.4782 0.095 Uiso 1 1 calc R . .
H1B H 0.5894 0.1602 0.5001 0.095 Uiso 1 1 calc R . .
H1C H 0.6869 0.0974 0.5045 0.095 Uiso 1 1 calc R . .
C2 C 0.5879(2) 0.1268(3) 0.3711(2) 0.0487(7) Uani 1 1 d . . .
C3 C 0.5423(2) 0.0607(3) 0.29013(19) 0.0465(7) Uani 1 1 d . . .
C4 C 0.5468(2) 0.1386(3) 0.21566(19) 0.0458(7) Uani 1 1 d . . .
C5 C 0.5937(2) 0.2467(3) 0.25450(18) 0.0446(7) Uani 1 1 d . . .
C6 C 0.4957(2) -0.0647(3) 0.27881(19) 0.0482(7) Uani 1 1 d . . .
C7 C 0.5339(2) -0.1675(3) 0.2507(2) 0.0597(9) Uani 1 1 d . . .
H7A H 0.5921 -0.1587 0.2420 0.072 Uiso 1 1 calc R . .
C8 C 0.4878(3) -0.2830(3) 0.2351(2) 0.0655(9) Uani 1 1 d . . .
H8A H 0.5148 -0.3506 0.2156 0.079 Uiso 1 1 calc R . .
C9 C 0.4018(3) -0.2987(3) 0.2483(2) 0.0566(8) Uani 1 1 d . . .
C10 C 0.3634(3) -0.1970(3) 0.2770(2) 0.0612(9) Uani 1 1 d . . .
H10A H 0.3058 -0.2067 0.2867 0.073 Uiso 1 1 calc R . .
C11 C 0.4085(2) -0.0816(3) 0.2915(2) 0.0554(8) Uani 1 1 d . . .
H11A H 0.3807 -0.0139 0.3100 0.067 Uiso 1 1 calc R . .
C12 C 0.3869(4) -0.5156(4) 0.2060(4) 0.1099(17) Uani 1 1 d . . .
H12A H 0.3428 -0.5852 0.1974 0.165 Uiso 1 1 calc R . .
H12B H 0.4503 -0.5356 0.2547 0.165 Uiso 1 1 calc R . .
H12C H 0.3936 -0.4992 0.1477 0.165 Uiso 1 1 calc R . .
C13 C 0.6259(2) 0.3597(3) 0.22153(19) 0.0466(7) Uani 1 1 d . . .
C14 C 0.6046(3) 0.3797(3) 0.1261(2) 0.0686(10) Uani 1 1 d . . .
H14A H 0.5698 0.3193 0.0815 0.082 Uiso 1 1 calc R . .
C15 C 0.6350(3) 0.4893(4) 0.0971(3) 0.0765(11) Uani 1 1 d . . .
H15A H 0.6195 0.5022 0.0330 0.092 Uiso 1 1 calc R . .
C16 C 0.6870(3) 0.5785(3) 0.1613(2) 0.0666(10) Uani 1 1 d . . .
H16A H 0.7072 0.6517 0.1412 0.080 Uiso 1 1 calc R . .
C17 C 0.7093(3) 0.5592(3) 0.2553(3) 0.0700(10) Uani 1 1 d . . .
H17A H 0.7453 0.6194 0.2995 0.084 Uiso 1 1 calc R . .
C18 C 0.6789(2) 0.4510(3) 0.2850(2) 0.0585(8) Uani 1 1 d . . .
H18A H 0.6946 0.4394 0.3493 0.070 Uiso 1 1 calc R . .
C19 C 0.3190(2) 0.0308(3) 0.04652(19) 0.0495(7) Uani 1 1 d . . .
C20 C 0.3228(3) -0.0930(3) 0.0224(2) 0.0606(9) Uani 1 1 d . . .
H20A H 0.3736 -0.1212 0.0067 0.073 Uiso 1 1 calc R . .
C21 C 0.2511(3) -0.1743(4) 0.0218(3) 0.0724(10) Uani 1 1 d . . .
H21A H 0.2544 -0.2582 0.0062 0.087 Uiso 1 1 calc R . .
C22 C 0.1737(3) -0.1351(4) 0.0437(3) 0.0731(10) Uani 1 1 d . . .
C23 C 0.1723(3) -0.0113(4) 0.0690(3) 0.0769(11) Uani 1 1 d . . .
H23A H 0.1221 0.0162 0.0860 0.092 Uiso 1 1 calc R . .
C24 C 0.2435(3) 0.0736(3) 0.0699(2) 0.0634(9) Uani 1 1 d . . .
H24A H 0.2407 0.1575 0.0858 0.076 Uiso 1 1 calc R . .
C25 C 0.0951(4) -0.2263(5) 0.0436(4) 0.1168(17) Uani 1 1 d . . .
H25A H 0.0478 -0.1825 0.0604 0.175 Uiso 1 1 calc R . .
H25B H 0.1252 -0.2920 0.0887 0.175 Uiso 1 1 calc R . .
H25C H 0.0625 -0.2621 -0.0185 0.175 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 O4 1.428(2) . ?
S1 O3 1.436(2) . ?
S1 N1 1.624(3) . ?
S1 C19 1.759(3) . ?
N1 C4 1.417(3) . ?
O1 C2 1.378(3) . ?
O1 C5 1.380(3) . ?
O2 C9 1.370(4) . ?
O2 C12 1.416(4) . ?
C1 C2 1.475(4) . ?
C2 C3 1.352(4) . ?
C3 C4 1.440(4) . ?
C3 C6 1.479(4) . ?
C4 C5 1.351(4) . ?
C5 C13 1.459(4) . ?
C6 C7 1.379(4) . ?
C6 C11 1.394(4) . ?
C7 C8 1.378(4) . ?
C8 C9 1.379(5) . ?
C9 C10 1.376(4) . ?
C10 C11 1.373(4) . ?
C13 C18 1.377(4) . ?
C13 C14 1.391(4) . ?
C14 C15 1.387(5) . ?
C15 C16 1.362(5) . ?
C16 C17 1.365(5) . ?
C17 C18 1.381(4) . ?
C19 C20 1.376(4) . ?
C19 C24 1.383(4) . ?
C20 C21 1.367(5) . ?
C21 C22 1.385(5) . ?
C22 C23 1.376(5) . ?
C22 C25 1.514(5) . ?
C23 C24 1.385(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 S1 O3 119.68(12) . . ?
O4 S1 N1 107.88(13) . . ?
O3 S1 N1 104.49(13) . . ?
O4 S1 C19 107.89(15) . . ?
O3 S1 C19 107.23(13) . . ?
N1 S1 C19 109.37(13) . . ?
C4 N1 S1 123.2(2) . . ?
C2 O1 C5 108.2(2) . . ?
C9 O2 C12 117.6(3) . . ?
C3 C2 O1 109.8(2) . . ?
C3 C2 C1 133.6(3) . . ?
O1 C2 C1 116.4(3) . . ?
C2 C3 C4 105.7(3) . . ?
C2 C3 C6 127.8(3) . . ?
C4 C3 C6 126.5(3) . . ?
C5 C4 N1 125.7(3) . . ?
C5 C4 C3 108.5(2) . . ?
N1 C4 C3 125.6(3) . . ?
C4 C5 O1 107.9(2) . . ?
C4 C5 C13 136.8(2) . . ?
O1 C5 C13 115.3(2) . . ?
C7 C6 C11 117.6(3) . . ?
C7 C6 C3 121.4(3) . . ?
C11 C6 C3 120.9(3) . . ?
C8 C7 C6 121.6(3) . . ?
C7 C8 C9 120.3(3) . . ?
O2 C9 C10 115.8(3) . . ?
O2 C9 C8 125.5(3) . . ?
C10 C9 C8 118.7(3) . . ?
C11 C10 C9 121.2(3) . . ?
C10 C11 C6 120.7(3) . . ?
C18 C13 C14 117.7(3) . . ?
C18 C13 C5 120.4(3) . . ?
C14 C13 C5 121.9(3) . . ?
C15 C14 C13 120.3(3) . . ?
C16 C15 C14 121.0(3) . . ?
C15 C16 C17 119.2(3) . . ?
C16 C17 C18 120.4(3) . . ?
C13 C18 C17 121.4(3) . . ?
C20 C19 C24 120.7(3) . . ?
C20 C19 S1 119.6(3) . . ?
C24 C19 S1 119.4(3) . . ?
C21 C20 C19 119.4(3) . . ?
C20 C21 C22 121.7(4) . . ?
C23 C22 C21 117.8(4) . . ?
C23 C22 C25 120.9(4) . . ?
C21 C22 C25 121.3(4) . . ?
C22 C23 C24 121.9(4) . . ?
C19 C24 C23 118.4(3) . . ?

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
O4 S1 N1 C4 36.7(3) . . . . ?
O3 S1 N1 C4 165.1(2) . . . . ?
C19 S1 N1 C4 -80.4(3) . . . . ?
C5 O1 C2 C3 -1.0(3) . . . . ?
C5 O1 C2 C1 174.6(3) . . . . ?
O1 C2 C3 C4 0.8(3) . . . . ?
C1 C2 C3 C4 -173.7(3) . . . . ?
O1 C2 C3 C6 -178.4(3) . . . . ?
C1 C2 C3 C6 7.2(6) . . . . ?
S1 N1 C4 C5 -89.8(4) . . . . ?
S1 N1 C4 C3 95.4(3) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C6 C3 C4 C5 178.8(3) . . . . ?
C2 C3 C4 N1 175.2(3) . . . . ?
C6 C3 C4 N1 -5.6(5) . . . . ?
N1 C4 C5 O1 -175.7(3) . . . . ?
C3 C4 C5 O1 -0.2(3) . . . . ?
N1 C4 C5 C13 1.3(6) . . . . ?
C3 C4 C5 C13 176.8(3) . . . . ?
C2 O1 C5 C4 0.7(3) . . . . ?
C2 O1 C5 C13 -177.0(2) . . . . ?
C2 C3 C6 C7 -113.4(4) . . . . ?
C4 C3 C6 C7 67.6(4) . . . . ?
C2 C3 C6 C11 70.0(4) . . . . ?
C4 C3 C6 C11 -109.1(4) . . . . ?
C11 C6 C7 C8 0.3(5) . . . . ?
C3 C6 C7 C8 -176.5(3) . . . . ?
C6 C7 C8 C9 -0.6(5) . . . . ?
C12 O2 C9 C10 -178.2(4) . . . . ?
C12 O2 C9 C8 3.6(5) . . . . ?
C7 C8 C9 O2 178.3(3) . . . . ?
C7 C8 C9 C10 0.1(5) . . . . ?
O2 C9 C10 C11 -177.7(3) . . . . ?
C8 C9 C10 C11 0.6(5) . . . . ?
C9 C10 C11 C6 -0.9(5) . . . . ?
C7 C6 C11 C10 0.5(5) . . . . ?
C3 C6 C11 C10 177.2(3) . . . . ?
C4 C5 C13 C18 -175.9(4) . . . . ?
O1 C5 C13 C18 0.9(4) . . . . ?
C4 C5 C13 C14 4.2(6) . . . . ?
O1 C5 C13 C14 -179.0(3) . . . . ?
C18 C13 C14 C15 -1.1(5) . . . . ?
C5 C13 C14 C15 178.9(3) . . . . ?
C13 C14 C15 C16 0.9(6) . . . . ?
C14 C15 C16 C17 -0.1(6) . . . . ?
C15 C16 C17 C18 -0.4(6) . . . . ?
C14 C13 C18 C17 0.6(5) . . . . ?
C5 C13 C18 C17 -179.4(3) . . . . ?
C16 C17 C18 C13 0.2(6) . . . . ?
O4 S1 C19 C20 175.3(2) . . . . ?
O3 S1 C19 C20 45.2(3) . . . . ?
N1 S1 C19 C20 -67.6(3) . . . . ?
O4 S1 C19 C24 -0.1(3) . . . . ?
O3 S1 C19 C24 -130.3(3) . . . . ?
N1 S1 C19 C24 117.0(3) . . . . ?
C24 C19 C20 C21 -0.1(5) . . . . ?
S1 C19 C20 C21 -175.5(3) . . . . ?
C19 C20 C21 C22 0.8(6) . . . . ?
C20 C21 C22 C23 -1.8(6) . . . . ?
C20 C21 C22 C25 -179.5(4) . . . . ?
C21 C22 C23 C24 2.1(6) . . . . ?
C25 C22 C23 C24 179.9(4) . . . . ?
C20 C19 C24 C23 0.4(5) . . . . ?
S1 C19 C24 C23 175.8(3) . . . . ?
C22 C23 C24 C19 -1.5(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.058
####################################################################### 
# 
# 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_Compound-4
_database_code_depnum_ccdc_archive 'CCDC 1444605'
_audit_update_record             
;
2015-12-29 deposited with the CCDC.
2016-03-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H25 N O3 S'
_chemical_formula_weight         479.57

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

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

_cell_length_a                   13.9018(4)
_cell_length_b                   17.5310(4)
_cell_length_c                   9.7328(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2372.00(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3042
_cell_measurement_theta_min      4.0480
_cell_measurement_theta_max      72.1990

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.479
_shelx_estimated_absorpt_T_min   0.737
_shelx_estimated_absorpt_T_max   0.891
_exptl_absorpt_correction_T_min  0.74892
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6140
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.058
_diffrn_reflns_theta_max         73.401
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.756
_diffrn_reflns_point_group_measured_fraction_full 0.789
_reflns_number_total             3611
_reflns_number_gt                3373
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.471
_reflns_Friedel_fraction_max     0.516
_reflns_Friedel_fraction_full    0.550

_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0440P)²+0.2203P] 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_abs_structure_details 
;
 Flack x determined using 1024 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(13)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3611
_refine_ls_number_parameters     317
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.0797
_refine_ls_wR_factor_gt          0.0766
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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 0.37203(4) 0.68900(3) 0.21696(7) 0.01995(14) Uani 1 1 d . . . . .
O1 O 0.40736(14) 0.67687(11) 0.0805(2) 0.0258(4) Uani 1 1 d . . . . .
O2 O 0.30359(12) 0.74838(9) 0.2445(2) 0.0247(4) Uani 1 1 d . . . . .
O3 O 0.34943(14) 0.83234(11) 0.5450(2) 0.0288(4) Uani 1 1 d . . . . .
N1 N 0.46533(15) 0.70781(12) 0.3119(2) 0.0205(4) Uani 1 1 d . . . . .
C1 C 0.1791(2) 0.39823(17) 0.4126(4) 0.0376(7) Uani 1 1 d . . . . .
H1A H 0.2056 0.3833 0.5020 0.056 Uiso 1 1 calc R U . . .
H1B H 0.1899 0.3572 0.3461 0.056 Uiso 1 1 calc R U . . .
H1C H 0.1100 0.4077 0.4216 0.056 Uiso 1 1 calc R U . . .
C2 C 0.22829(19) 0.46971(15) 0.3636(3) 0.0260(6) Uani 1 1 d . . . . .
C3 C 0.20302(18) 0.54059(15) 0.4181(3) 0.0264(6) Uani 1 1 d . . . . .
H3 H 0.1548 0.5432 0.4871 0.032 Uiso 1 1 calc R U . . .
C4 C 0.24657(17) 0.60721(15) 0.3739(3) 0.0229(5) Uani 1 1 d . . . . .
H4 H 0.2275 0.6551 0.4107 0.027 Uiso 1 1 calc R U . . .
C5 C 0.31862(17) 0.60323(14) 0.2748(3) 0.0206(5) Uani 1 1 d . . . . .
C6 C 0.34605(18) 0.53312(13) 0.2184(3) 0.0245(5) Uani 1 1 d . . . . .
H6 H 0.3953 0.5305 0.1509 0.029 Uiso 1 1 calc R U . . .
C7 C 0.2996(2) 0.46727(15) 0.2632(3) 0.0281(6) Uani 1 1 d . . . . .
H7 H 0.3171 0.4195 0.2244 0.034 Uiso 1 1 calc R U . . .
C8 C 0.51213(18) 0.87795(14) 0.2645(3) 0.0253(6) Uani 1 1 d . . . . .
H8 H 0.5489 0.8324 0.2589 0.030 Uiso 1 1 calc R U . . .
C9 C 0.5358(2) 0.93983(16) 0.1818(3) 0.0317(7) Uani 1 1 d . . . . .
H9 H 0.5881 0.9363 0.1194 0.038 Uiso 1 1 calc R U . . .
C10 C 0.4830(2) 1.00670(16) 0.1904(3) 0.0344(7) Uani 1 1 d . . . . .
H10 H 0.5005 1.0496 0.1362 0.041 Uiso 1 1 calc R U . . .
C11 C 0.4047(3) 1.01097(16) 0.2782(4) 0.0374(7) Uani 1 1 d . . . . .
H11 H 0.3672 1.0562 0.2815 0.045 Uiso 1 1 calc R U . . .
C12 C 0.3807(2) 0.94975(16) 0.3610(4) 0.0314(6) Uani 1 1 d . . . . .
H12 H 0.3274 0.9534 0.4217 0.038 Uiso 1 1 calc R U . . .
C13 C 0.43472(18) 0.88231(14) 0.3558(3) 0.0227(5) Uani 1 1 d . . . . .
C14 C 0.40781(18) 0.82035(14) 0.4542(3) 0.0211(5) Uani 1 1 d . . . . .
C15 C 0.45373(17) 0.73992(13) 0.4500(3) 0.0191(5) Uani 1 1 d . . . . .
H15 H 0.4129 0.7044 0.5054 0.023 Uiso 1 1 calc R U . . .
C16 C 0.55619(17) 0.73705(13) 0.5059(3) 0.0204(5) Uani 1 1 d . . . . .
C17 C 0.61475(17) 0.70653(14) 0.4127(3) 0.0215(5) Uani 1 1 d . . . . .
H17 H 0.6819 0.7008 0.4273 0.026 Uiso 1 1 calc R U . . .
C18 C 0.56604(17) 0.68200(14) 0.2828(3) 0.0210(5) Uani 1 1 d . . . . .
H18 H 0.5927 0.7114 0.2035 0.025 Uiso 1 1 calc R U . . .
C19 C 0.57747(18) 0.59679(14) 0.2565(3) 0.0214(5) Uani 1 1 d . . . . .
C20 C 0.5775(2) 0.54515(16) 0.3649(3) 0.0272(6) Uani 1 1 d . . . . .
H20 H 0.5710 0.5631 0.4566 0.033 Uiso 1 1 calc R U . . .
C21 C 0.5870(2) 0.46741(17) 0.3399(3) 0.0326(7) Uani 1 1 d . . . . .
H21 H 0.5866 0.4323 0.4142 0.039 Uiso 1 1 calc R U . . .
C22 C 0.5970(2) 0.44146(15) 0.2065(3) 0.0301(6) Uani 1 1 d . . . . .
H22 H 0.6032 0.3883 0.1893 0.036 Uiso 1 1 calc R U . . .
C23 C 0.5982(2) 0.49245(16) 0.0978(3) 0.0273(6) Uani 1 1 d . . . . .
H23 H 0.6049 0.4743 0.0063 0.033 Uiso 1 1 calc R U . . .
C24 C 0.58963(19) 0.57003(16) 0.1229(3) 0.0245(6) Uani 1 1 d . . . . .
H24 H 0.5921 0.6051 0.0486 0.029 Uiso 1 1 calc R U . . .
C25 C 0.58249(18) 0.76041(13) 0.6471(3) 0.0205(5) Uani 1 1 d . . . . .
C26 C 0.51401(19) 0.76775(14) 0.7518(3) 0.0254(6) Uani 1 1 d . . . . .
H26 H 0.4477 0.7618 0.7307 0.031 Uiso 1 1 calc R U . . .
C27 C 0.5414(2) 0.78355(16) 0.8853(3) 0.0272(6) Uani 1 1 d . . . . .
H27 H 0.4938 0.7882 0.9547 0.033 Uiso 1 1 calc R U . . .
C28 C 0.6378(2) 0.79275(15) 0.9192(3) 0.0277(6) Uani 1 1 d . . . . .
H28 H 0.6563 0.8028 1.0114 0.033 Uiso 1 1 calc R U . . .
C29 C 0.7066(2) 0.78701(15) 0.8161(3) 0.0263(6) Uani 1 1 d . . . . .
H29 H 0.7726 0.7943 0.8376 0.032 Uiso 1 1 calc R U . . .
C30 C 0.67961(18) 0.77072(15) 0.6822(3) 0.0240(6) Uani 1 1 d . . . . .
H30 H 0.7276 0.7665 0.6131 0.029 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 1.432(2) . ?
S1 O2 1.4356(18) . ?
S1 N1 1.626(2) . ?
S1 C5 1.769(3) . ?
O3 C14 1.218(3) . ?
N1 C15 1.467(3) . ?
N1 C18 1.498(3) . ?
C1 C2 1.505(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C7 1.393(4) . ?
C2 C3 1.396(4) . ?
C3 C4 1.384(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.399(4) . ?
C6 C7 1.393(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.390(4) . ?
C8 C13 1.398(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.385(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.401(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.496(4) . ?
C14 C15 1.548(3) . ?
C15 C16 1.526(4) . ?
C15 H15 1.0000 . ?
C16 C17 1.331(4) . ?
C16 C25 1.480(4) . ?
C17 C18 1.497(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.524(3) . ?
C18 H18 1.0000 . ?
C19 C20 1.390(4) . ?
C19 C24 1.393(4) . ?
C20 C21 1.391(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.383(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.385(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.387(4) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C26 1.400(4) . ?
C25 C30 1.404(4) . ?
C26 C27 1.382(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.389(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.390(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.386(4) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?

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 120.55(12) . . ?
O1 S1 N1 106.47(12) . . ?
O2 S1 N1 105.99(11) . . ?
O1 S1 C5 108.23(12) . . ?
O2 S1 C5 106.18(11) . . ?
N1 S1 C5 109.05(12) . . ?
C15 N1 C18 113.1(2) . . ?
C15 N1 S1 120.73(17) . . ?
C18 N1 S1 125.24(19) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 118.2(2) . . ?
C7 C2 C1 121.3(3) . . ?
C3 C2 C1 120.5(3) . . ?
C4 C3 C2 121.6(3) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 119.2(2) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 120.8(2) . . ?
C4 C5 S1 118.7(2) . . ?
C6 C5 S1 120.5(2) . . ?
C7 C6 C5 118.6(3) . . ?
C7 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C6 C7 C2 121.6(3) . . ?
C6 C7 H7 119.2 . . ?
C2 C7 H7 119.2 . . ?
C9 C8 C13 120.5(2) . . ?
C9 C8 H8 119.8 . . ?
C13 C8 H8 119.8 . . ?
C10 C9 C8 120.0(3) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 119.9(3) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 120.3(3) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C8 C13 C12 118.8(3) . . ?
C8 C13 C14 124.1(2) . . ?
C12 C13 C14 117.1(3) . . ?
O3 C14 C13 120.4(2) . . ?
O3 C14 C15 116.8(2) . . ?
C13 C14 C15 122.8(2) . . ?
N1 C15 C16 102.2(2) . . ?
N1 C15 C14 114.8(2) . . ?
C16 C15 C14 113.9(2) . . ?
N1 C15 H15 108.5 . . ?
C16 C15 H15 108.5 . . ?
C14 C15 H15 108.5 . . ?
C17 C16 C25 126.4(2) . . ?
C17 C16 C15 109.9(2) . . ?
C25 C16 C15 123.6(2) . . ?
C16 C17 C18 114.5(2) . . ?
C16 C17 H17 122.8 . . ?
C18 C17 H17 122.8 . . ?
C17 C18 N1 100.2(2) . . ?
C17 C18 C19 112.1(2) . . ?
N1 C18 C19 115.2(2) . . ?
C17 C18 H18 109.7 . . ?
N1 C18 H18 109.7 . . ?
C19 C18 H18 109.7 . . ?
C20 C19 C24 119.3(2) . . ?
C20 C19 C18 120.7(3) . . ?
C24 C19 C18 120.0(2) . . ?
C19 C20 C21 120.4(3) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C22 C21 C20 119.7(3) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C21 C22 C23 120.4(3) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C24 119.8(3) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C23 C24 C19 120.3(3) . . ?
C23 C24 H24 119.8 . . ?
C19 C24 H24 119.8 . . ?
C26 C25 C30 117.7(3) . . ?
C26 C25 C16 122.2(2) . . ?
C30 C25 C16 119.9(2) . . ?
C27 C26 C25 121.0(2) . . ?
C27 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C26 C27 C28 120.9(3) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 H27 119.6 . . ?
C27 C28 C29 118.9(3) . . ?
C27 C28 H28 120.5 . . ?
C29 C28 H28 120.5 . . ?
C30 C29 C28 120.5(3) . . ?
C30 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
C29 C30 C25 121.0(3) . . ?
C29 C30 H30 119.5 . . ?
C25 C30 H30 119.5 . . ?

_refine_diff_density_max         0.210
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.039

_shelxl_version_number           2014-3

