# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1402446'
_audit_update_record             
;
2015-05-22 deposited with the CCDC.
2015-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_absolute_configuration ad
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H11 N O4 S'
_chemical_formula_weight         325.33

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           trigonal
_symmetry_space_group_name_H-M   P32

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'

_cell_length_a                   11.56100(10)
_cell_length_b                   11.56100(10)
_cell_length_c                   9.7070(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     1123.59(3)
_cell_formula_units_Z            3
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1722
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9906
_exptl_absorpt_correction_T_max  0.9930
_exptl_absorpt_process_details   'Empirical absorption correction:XABS2'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3421
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3421
_reflns_number_gt                2913
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       COLLECT
_computing_cell_refinement       'HKL DENZO'
_computing_data_reduction        'HKL DENZO and SCALEPACK'
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0898P)²+0.0372P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(8)
_refine_ls_number_reflns         3421
_refine_ls_number_parameters     212
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1156
_refine_ls_wR_factor_gt          0.1063
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_restrained_S_all      0.941
_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
S S 1.12743(5) 0.94689(5) 0.36406(7) 0.04915(17) Uani 1 1 d . . .
O1 O 1.14433(18) 0.8906(2) 0.48740(18) 0.0586(5) Uani 1 1 d . . .
O2 O 1.1839(2) 1.0863(2) 0.3511(3) 0.0801(7) Uani 1 1 d . . .
O3 O 1.19208(17) 0.90648(19) 0.2433(2) 0.0601(5) Uani 1 1 d . . .
O4 O 0.8360(2) 0.8077(2) 0.0843(2) 0.0663(5) Uani 1 1 d . . .
N N 0.9711(2) 0.87251(19) 0.3271(2) 0.0515(5) Uani 1 1 d . . .
C1 C 0.9090(2) 0.7244(2) 0.3212(2) 0.0405(5) Uani 1 1 d . . .
C2 C 0.9931(2) 0.6829(2) 0.2359(2) 0.0445(5) Uani 1 1 d . . .
C3 C 1.1266(2) 0.7705(3) 0.2058(3) 0.0503(6) Uani 1 1 d . . .
C4 C 1.2043(3) 0.7311(4) 0.1337(3) 0.0721(8) Uani 1 1 d . . .
H4 H 1.2928 0.7923 0.1128 0.086 Uiso 1 1 calc R . .
C5 C 1.1480(4) 0.5984(4) 0.0933(3) 0.0806(10) Uani 1 1 d . . .
H5 H 1.1993 0.5699 0.0461 0.097 Uiso 1 1 calc R . .
C6 C 1.0163(4) 0.5092(4) 0.1230(4) 0.0728(9) Uani 1 1 d . . .
H6 H 0.9788 0.4201 0.0969 0.087 Uiso 1 1 calc R . .
C7 C 0.9409(3) 0.5518(3) 0.1909(3) 0.0579(7) Uani 1 1 d . . .
H7 H 0.8513 0.4910 0.2078 0.070 Uiso 1 1 calc R . .
C8 C 0.7654(2) 0.6614(2) 0.2749(2) 0.0419(5) Uani 1 1 d . . .
C9 C 0.7330(2) 0.7081(2) 0.1584(3) 0.0495(5) Uani 1 1 d . . .
C10 C 0.6001(3) 0.6562(3) 0.1153(3) 0.0588(7) Uani 1 1 d . . .
H10 H 0.5809 0.6916 0.0385 0.071 Uiso 1 1 calc R . .
C11 C 0.4996(3) 0.5539(3) 0.1866(3) 0.0575(7) Uani 1 1 d . . .
H11 H 0.4117 0.5201 0.1581 0.069 Uiso 1 1 calc R . .
C12 C 0.5267(2) 0.4983(2) 0.3031(3) 0.0482(6) Uani 1 1 d . . .
C13 C 0.4223(3) 0.3883(3) 0.3759(3) 0.0587(7) Uani 1 1 d . . .
H13 H 0.3344 0.3540 0.3472 0.070 Uiso 1 1 calc R . .
C14 C 0.4482(3) 0.3325(3) 0.4858(3) 0.0639(7) Uani 1 1 d . . .
H14 H 0.3788 0.2609 0.5320 0.077 Uiso 1 1 calc R . .
C15 C 0.5805(3) 0.3838(3) 0.5293(3) 0.0580(6) Uani 1 1 d . . .
H15 H 0.5987 0.3447 0.6037 0.070 Uiso 1 1 calc R . .
C16 C 0.6830(3) 0.4901(2) 0.4641(3) 0.0490(5) Uani 1 1 d . . .
H16 H 0.7697 0.5231 0.4963 0.059 Uiso 1 1 calc R . .
C17 C 0.6609(2) 0.5520(2) 0.3480(2) 0.0418(5) Uani 1 1 d . . .
H1 H 0.911(3) 0.703(3) 0.418(3) 0.049(7) Uiso 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
S O1 1.422(2) . ?
S O2 1.410(2) . ?
S O3 1.581(2) . ?
S N 1.606(2) . ?
O3 C3 1.409(3) . ?
O4 C9 1.375(3) . ?
N C1 1.491(3) . ?
C1 C8 1.510(3) . ?
C1 C2 1.525(3) . ?
C1 H1 0.98(3) . ?
C2 C7 1.392(4) . ?
C2 C3 1.389(4) . ?
C3 C4 1.384(4) . ?
C4 C5 1.390(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.367(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.383(3) . ?
C8 C17 1.426(3) . ?
C9 C10 1.405(3) . ?
C10 C11 1.362(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.411(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.427(4) . ?
C12 C17 1.422(3) . ?
C13 C14 1.356(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.400(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.363(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.425(3) . ?
C16 H16 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 S O1 120.49(13) . . ?
O2 S O3 104.74(14) . . ?
O1 S O3 107.18(11) . . ?
O2 S N 110.25(12) . . ?
O1 S N 108.56(12) . . ?
O3 S N 104.36(10) . . ?
C3 O3 S 116.84(16) . . ?
C1 N S 112.96(15) . . ?
N C1 C8 110.29(18) . . ?
N C1 C2 111.44(19) . . ?
C8 C1 C2 114.05(18) . . ?
N C1 H1 101.2(16) . . ?
C8 C1 H1 109.1(16) . . ?
C2 C1 H1 110.0(16) . . ?
C7 C2 C3 116.5(2) . . ?
C7 C2 C1 121.0(2) . . ?
C3 C2 C1 122.4(2) . . ?
C4 C3 C2 122.3(3) . . ?
C4 C3 O3 115.0(2) . . ?
C2 C3 O3 122.7(2) . . ?
C3 C4 C5 118.9(3) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C7 C6 C5 119.8(3) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C2 122.4(3) . . ?
C6 C7 H7 118.8 . . ?
C2 C7 H7 118.8 . . ?
C9 C8 C17 118.6(2) . . ?
C9 C8 C1 120.1(2) . . ?
C17 C8 C1 121.25(19) . . ?
O4 C9 C8 117.7(2) . . ?
O4 C9 C10 120.4(2) . . ?
C8 C9 C10 121.9(2) . . ?
C11 C10 C9 119.7(2) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 121.0(2) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C11 C12 C13 121.4(2) . . ?
C11 C12 C17 119.3(2) . . ?
C13 C12 C17 119.3(2) . . ?
C14 C13 C12 121.6(2) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C15 119.3(3) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C16 C15 C14 121.0(3) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 121.8(2) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 H16 119.1 . . ?
C16 C17 C12 117.0(2) . . ?
C16 C17 C8 123.67(19) . . ?
C12 C17 C8 119.3(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1402447'
_audit_update_record             
;
2015-05-22 deposited with the CCDC.
2015-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_absolute_configuration ad
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 N O4 S'
_chemical_formula_weight         339.35

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           orthorhombic
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   7.62700(10)
_cell_length_b                   10.3530(2)
_cell_length_c                   18.9970(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1500.05(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2008
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9765
_exptl_absorpt_correction_T_max  0.9905
_exptl_absorpt_process_details   'Empirical absorption correction:XABS2'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3426
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.32
_diffrn_reflns_theta_max         27.49
_reflns_number_total             3426
_reflns_number_gt                2603
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       COLLECT
_computing_cell_refinement       'HKL DENZO'
_computing_data_reduction        'HKL DENZO and SCALEPACK'
_computing_structure_solution    SHELXS-97
_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)+(0.0625P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(7)
_refine_ls_number_reflns         3426
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.0970
_refine_ls_wR_factor_gt          0.0893
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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
S S -0.78008(7) 0.10756(5) -0.44569(3) 0.05411(17) Uani 1 1 d . . .
O1 O -0.8054(2) 0.06632(14) -0.24595(8) 0.0576(4) Uani 1 1 d . . .
O2 O -0.9783(2) 0.08483(14) -0.46743(8) 0.0641(4) Uani 1 1 d . . .
O3 O -0.6740(2) 0.03392(18) -0.49181(9) 0.0770(5) Uani 1 1 d . . .
O4 O -0.7628(2) 0.24268(15) -0.44124(9) 0.0749(5) Uani 1 1 d . . .
N N -0.7691(2) 0.04296(14) -0.36784(8) 0.0453(4) Uani 1 1 d . . .
C1 C -0.8091(2) -0.09713(18) -0.36916(9) 0.0393(4) Uani 1 1 d . . .
C2 C -0.7790(2) -0.14785(18) -0.29546(9) 0.0393(4) Uani 1 1 d . . .
C3 C -0.7333(3) -0.27993(19) -0.28321(9) 0.0409(4) Uani 1 1 d . . .
C4 C -0.7229(3) -0.3715(2) -0.33820(10) 0.0476(5) Uani 1 1 d . . .
H4 H -0.7426 -0.3451 -0.3843 0.057 Uiso 1 1 calc R . .
C5 C -0.6842(3) -0.4981(2) -0.32481(13) 0.0589(6) Uani 1 1 d . . .
H5 H -0.6813 -0.5574 -0.3615 0.071 Uiso 1 1 calc R . .
C6 C -0.6491(3) -0.5385(2) -0.25607(14) 0.0607(6) Uani 1 1 d . . .
H6 H -0.6231 -0.6247 -0.2471 0.073 Uiso 1 1 calc R . .
C7 C -0.6529(3) -0.4529(2) -0.20290(12) 0.0536(6) Uani 1 1 d . . .
H7 H -0.6265 -0.4808 -0.1576 0.064 Uiso 1 1 calc R . .
C8 C -0.6957(2) -0.3222(2) -0.21391(10) 0.0456(5) Uani 1 1 d . . .
C9 C -0.7074(3) -0.2324(2) -0.15828(10) 0.0562(6) Uani 1 1 d . . .
H9 H -0.6856 -0.2598 -0.1125 0.067 Uiso 1 1 calc R . .
C10 C -0.7499(3) -0.1067(2) -0.17008(10) 0.0588(6) Uani 1 1 d . . .
H10 H -0.7579 -0.0491 -0.1327 0.071 Uiso 1 1 calc R . .
C11 C -0.7818(3) -0.06429(19) -0.23939(10) 0.0466(5) Uani 1 1 d . . .
C12 C -0.8693(3) 0.1083(2) -0.31192(11) 0.0531(5) Uani 1 1 d . . .
H23A H -0.8559 0.2011 -0.3161 0.064 Uiso 1 1 calc R . .
H23B H -0.9928 0.0875 -0.3162 0.064 Uiso 1 1 calc R . .
C13 C -1.0624(3) -0.03228(18) -0.44862(10) 0.0459(5) Uani 1 1 d . . .
C14 C -1.2255(3) -0.04742(19) -0.47841(10) 0.0506(5) Uani 1 1 d . . .
H14 H -1.2686 0.0132 -0.5101 0.061 Uiso 1 1 calc R . .
C15 C -1.3237(3) -0.1541(2) -0.46036(10) 0.0515(5) Uani 1 1 d . . .
H15 H -1.4329 -0.1671 -0.4810 0.062 Uiso 1 1 calc R . .
C16 C -1.2610(3) -0.2411(2) -0.41208(11) 0.0506(5) Uani 1 1 d . . .
H16 H -1.3284 -0.3124 -0.3995 0.061 Uiso 1 1 calc R . .
C17 C -1.0968(3) -0.22273(19) -0.38203(10) 0.0443(5) Uani 1 1 d . . .
H17 H -1.0561 -0.2818 -0.3490 0.053 Uiso 1 1 calc R . .
C18 C -0.9922(3) -0.11832(18) -0.40017(8) 0.0387(4) Uani 1 1 d . . .
H1 H -0.720(2) -0.1422(18) -0.4001(9) 0.038(5) Uiso 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
S O4 1.4076(17) . ?
S O3 1.4155(18) . ?
S O2 1.5845(16) . ?
S N 1.6252(17) . ?
O1 C11 1.370(2) . ?
O1 C12 1.413(3) . ?
O2 C13 1.418(2) . ?
N C12 1.473(3) . ?
N C1 1.482(2) . ?
C1 C2 1.513(2) . ?
C1 C18 1.531(3) . ?
C1 H1 1.011(18) . ?
C2 C11 1.372(3) . ?
C2 C3 1.430(3) . ?
C3 C4 1.413(3) . ?
C3 C8 1.417(3) . ?
C4 C5 1.367(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.397(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.344(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.407(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.410(3) . ?
C9 C10 1.360(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.409(3) . ?
C10 H10 0.9300 . ?
C12 H23A 0.9700 . ?
C12 H23B 0.9700 . ?
C13 C14 1.376(3) . ?
C13 C18 1.388(3) . ?
C14 C15 1.378(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.390(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.387(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
O4 S O3 121.27(11) . . ?
O4 S O2 104.61(10) . . ?
O3 S O2 107.69(11) . . ?
O4 S N 110.46(10) . . ?
O3 S N 108.19(9) . . ?
O2 S N 103.02(8) . . ?
C11 O1 C12 115.43(15) . . ?
C13 O2 S 119.54(13) . . ?
C12 N C1 110.76(15) . . ?
C12 N S 116.14(13) . . ?
C1 N S 112.12(12) . . ?
N C1 C2 107.02(14) . . ?
N C1 C18 109.55(16) . . ?
C2 C1 C18 116.40(15) . . ?
N C1 H1 108.9(10) . . ?
C2 C1 H1 106.0(10) . . ?
C18 C1 H1 108.7(10) . . ?
C11 C2 C3 118.70(16) . . ?
C11 C2 C1 119.81(17) . . ?
C3 C2 C1 121.29(15) . . ?
C4 C3 C8 117.93(19) . . ?
C4 C3 C2 122.33(16) . . ?
C8 C3 C2 119.75(17) . . ?
C5 C4 C3 121.17(19) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 120.1(2) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 121.8(2) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
C7 C8 C9 122.47(19) . . ?
C7 C8 C3 118.8(2) . . ?
C9 C8 C3 118.67(19) . . ?
C10 C9 C8 121.49(18) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C11 119.56(19) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
O1 C11 C2 123.62(17) . . ?
O1 C11 C10 114.53(17) . . ?
C2 C11 C10 121.7(2) . . ?
O1 C12 N 108.66(16) . . ?
O1 C12 H23A 110.0 . . ?
N C12 H23A 110.0 . . ?
O1 C12 H23B 110.0 . . ?
N C12 H23B 110.0 . . ?
H23A C12 H23B 108.3 . . ?
C14 C13 C18 123.25(18) . . ?
C14 C13 O2 113.76(17) . . ?
C18 C13 O2 122.79(17) . . ?
C15 C14 C13 118.72(19) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C16 C15 C14 120.24(19) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 119.9(2) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 121.55(19) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C13 C18 C17 116.30(18) . . ?
C13 C18 C1 120.98(17) . . ?
C17 C18 C1 122.72(17) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.048
