# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_150705a
_database_code_depnum_ccdc_archive 'CCDC 1541032'
_audit_update_record             
;
2017-11-27 deposited with the CCDC.
2017-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H22 N2 O4 S'
_chemical_formula_weight         386.46

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   8.3685(9)
_cell_length_b                   6.1721(3)
_cell_length_c                   18.2702(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.7270(10)
_cell_angle_gamma                90.00
_cell_volume                     938.97(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    699
_cell_measurement_theta_min      4.8620
_cell_measurement_theta_max      63.3580

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    1.777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6177
_exptl_absorpt_correction_T_max  0.8709
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3016
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_sigmaI/netI    0.0845
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.87
_diffrn_reflns_theta_max         66.18
_reflns_number_total             1994
_reflns_number_gt                1299
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_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)+(0.0355P)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   0.02(7)
_chemical_absolute_configuration R/S
_refine_ls_number_reflns         1994
_refine_ls_number_parameters     257
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1279
_refine_ls_wR_factor_gt          0.1148
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.2360(2) 0.2760(5) 0.97811(8) 0.0564(5) Uani 1 1 d . . .
N1 N 0.2782(6) 0.5185(9) 0.7838(3) 0.0429(14) Uani 1 1 d . . .
H1 H 0.2662 0.6443 0.7637 0.051 Uiso 1 1 calc R . .
N2 N 0.2741(7) 0.1178(9) 0.8446(3) 0.0468(15) Uani 1 1 d . . .
H2 H 0.2559 -0.0045 0.8647 0.056 Uiso 1 1 calc R . .
O1 O 0.3187(6) 0.6786(7) 0.8950(2) 0.0595(14) Uani 1 1 d . . .
O2 O 0.2029(6) -0.0387(8) 0.7351(2) 0.0522(13) Uani 1 1 d . . .
O3 O 0.144(13) 0.383(11) 0.524(3) 0.065(13) Uani 0.6(2) 1 d P A 1
H3 H 0.1025 0.4076 0.4820 0.097 Uiso 0.6(2) 1 calc PR A 1
O3' O 0.082(17) 0.45(2) 0.536(4) 0.06(2) Uani 0.4(2) 1 d P A 2
H3' H 0.0513 0.4489 0.4920 0.094 Uiso 0.4(2) 1 calc PR A 2
O4 O 0.0228(10) 0.4265(18) 0.3870(4) 0.127(3) Uani 1 1 d . . .
H4 H -0.0545 0.4549 0.3574 0.191 Uiso 1 1 calc R . .
C1 C 0.3080(9) 0.5134(11) 0.8575(3) 0.0477(18) Uani 1 1 d . . .
C2 C 0.3340(8) 0.2890(12) 0.8942(3) 0.0426(15) Uani 1 1 d . . .
C3 C 0.2435(8) 0.1265(11) 0.7716(4) 0.0431(17) Uani 1 1 d . . .
C4 C 0.2646(8) 0.3380(10) 0.7360(3) 0.0440(17) Uani 1 1 d . . .
C5 C 0.2744(8) 0.3519(10) 0.6636(3) 0.0491(18) Uani 1 1 d . . .
H5 H 0.2549 0.2234 0.6376 0.059 Uiso 1 1 calc R . .
C6 C 0.3112(9) 0.5393(11) 0.6188(3) 0.0463(17) Uani 1 1 d . A .
C7 C 0.2330(10) 0.5572(13) 0.5489(4) 0.061(2) Uani 1 1 d . . .
C8 C 0.2688(9) 0.7270(13) 0.5027(4) 0.062(2) Uani 1 1 d . A .
H8 H 0.2140 0.7399 0.4560 0.074 Uiso 1 1 calc R . .
C9 C 0.3852(9) 0.8749(12) 0.5264(4) 0.060(2) Uani 1 1 d . . .
H9 H 0.4094 0.9885 0.4960 0.072 Uiso 1 1 calc R A .
C10 C 0.4652(9) 0.8545(12) 0.5948(4) 0.059(2) Uani 1 1 d . A .
H10 H 0.5448 0.9539 0.6106 0.070 Uiso 1 1 calc R . .
C11 C 0.4294(9) 0.6884(12) 0.6409(4) 0.0529(18) Uani 1 1 d . . .
H11 H 0.4854 0.6765 0.6873 0.063 Uiso 1 1 calc R A .
C12 C 0.5155(8) 0.2601(13) 0.9167(3) 0.0541(18) Uani 1 1 d . . .
H12A H 0.5499 0.3702 0.9528 0.065 Uiso 1 1 calc R . .
H12B H 0.5324 0.1201 0.9404 0.065 Uiso 1 1 calc R . .
C13 C 0.6182(8) 0.2737(13) 0.8555(3) 0.0545(18) Uani 1 1 d . . .
C14 C 0.6879(10) 0.4663(14) 0.8396(4) 0.065(2) Uani 1 1 d . . .
H14 H 0.6690 0.5882 0.8673 0.078 Uiso 1 1 calc R . .
C15 C 0.7863(11) 0.4846(16) 0.7828(5) 0.077(3) Uani 1 1 d . . .
H15 H 0.8346 0.6161 0.7734 0.092 Uiso 1 1 calc R . .
C16 C 0.8117(10) 0.3002(19) 0.7400(5) 0.084(3) Uani 1 1 d . . .
H16 H 0.8757 0.3100 0.7013 0.100 Uiso 1 1 calc R . .
C17 C 0.7435(11) 0.1106(16) 0.7549(5) 0.082(3) Uani 1 1 d . . .
H17 H 0.7592 -0.0102 0.7261 0.098 Uiso 1 1 calc R . .
C18 C 0.6488(10) 0.0938(13) 0.8137(5) 0.069(2) Uani 1 1 d . . .
H18 H 0.6059 -0.0398 0.8248 0.082 Uiso 1 1 calc R . .
C19 C 0.0295(9) 0.3167(14) 0.9436(4) 0.079(2) Uani 1 1 d . . .
H19A H -0.0056 0.1992 0.9115 0.119 Uiso 1 1 calc R . .
H19B H 0.0191 0.4507 0.9169 0.119 Uiso 1 1 calc R . .
H19C H -0.0355 0.3218 0.9840 0.119 Uiso 1 1 calc R . .
C20 C 0.0775(15) 0.223(3) 0.3735(7) 0.135(5) Uani 1 1 d . . .
H20A H 0.1672 0.2334 0.3448 0.202 Uiso 1 1 calc R . .
H20B H -0.0068 0.1412 0.3469 0.202 Uiso 1 1 calc R . .
H20C H 0.1104 0.1524 0.4193 0.202 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 C19 1.797(7) . ?
S1 C2 1.812(6) . ?
N1 C1 1.346(8) . ?
N1 C4 1.412(7) . ?
N1 H1 0.8600 . ?
N2 C3 1.334(8) . ?
N2 C2 1.448(8) . ?
N2 H2 0.8600 . ?
O1 C1 1.226(7) . ?
O2 C3 1.247(7) . ?
O3 C7 1.36(2) . ?
O3 H3 0.8200 . ?
O3' C7 1.44(7) . ?
O3' H3' 0.8200 . ?
O4 C20 1.366(15) . ?
O4 H4 0.8200 . ?
C1 C2 1.544(9) . ?
C2 C12 1.544(8) . ?
C3 C4 1.477(8) . ?
C4 C5 1.337(8) . ?
C5 C6 1.467(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.380(8) . ?
C6 C11 1.381(9) . ?
C7 C8 1.397(9) . ?
C8 C9 1.373(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.363(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.378(9) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.479(8) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.369(11) . ?
C13 C18 1.387(9) . ?
C14 C15 1.391(11) . ?
C14 H14 0.9300 . ?
C15 C16 1.409(12) . ?
C15 H15 0.9300 . ?
C16 C17 1.342(13) . ?
C16 H16 0.9300 . ?
C17 C18 1.401(12) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
C19 S1 C2 101.4(3) . . ?
C1 N1 C4 126.5(6) . . ?
C1 N1 H1 116.7 . . ?
C4 N1 H1 116.7 . . ?
C3 N2 C2 128.0(6) . . ?
C3 N2 H2 116.0 . . ?
C2 N2 H2 116.0 . . ?
C7 O3 H3 109.5 . . ?
C7 O3' H3' 109.5 . . ?
C20 O4 H4 109.5 . . ?
O1 C1 N1 122.3(6) . . ?
O1 C1 C2 120.3(5) . . ?
N1 C1 C2 117.3(6) . . ?
N2 C2 C12 110.7(5) . . ?
N2 C2 C1 111.0(5) . . ?
C12 C2 C1 108.2(6) . . ?
N2 C2 S1 109.8(5) . . ?
C12 C2 S1 106.6(4) . . ?
C1 C2 S1 110.5(5) . . ?
O2 C3 N2 121.1(6) . . ?
O2 C3 C4 121.7(5) . . ?
N2 C3 C4 117.1(6) . . ?
C5 C4 N1 123.5(6) . . ?
C5 C4 C3 120.9(6) . . ?
N1 C4 C3 115.5(5) . . ?
C4 C5 C6 129.7(6) . . ?
C4 C5 H5 115.1 . . ?
C6 C5 H5 115.1 . . ?
C7 C6 C11 118.5(6) . . ?
C7 C6 C5 118.2(6) . . ?
C11 C6 C5 123.2(6) . . ?
O3 C7 C6 116.3(11) . . ?
O3 C7 C8 122.1(13) . . ?
C6 C7 C8 120.6(7) . . ?
O3 C7 O3' 29(2) . . ?
C6 C7 O3' 116.2(14) . . ?
C8 C7 O3' 120(2) . . ?
C9 C8 C7 119.7(7) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C10 C9 C8 119.7(7) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 120.8(7) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C6 120.7(6) . . ?
C10 C11 H11 119.7 . . ?
C6 C11 H11 119.7 . . ?
C13 C12 C2 114.9(5) . . ?
C13 C12 H12A 108.5 . . ?
C2 C12 H12A 108.5 . . ?
C13 C12 H12B 108.5 . . ?
C2 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
C14 C13 C18 118.1(7) . . ?
C14 C13 C12 120.2(7) . . ?
C18 C13 C12 121.6(7) . . ?
C13 C14 C15 121.8(8) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C14 C15 C16 118.8(9) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C17 C16 C15 120.1(9) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.3(9) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C13 C18 C17 120.9(9) . . ?
C13 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
S1 C19 H19A 109.5 . . ?
S1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
S1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_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 N1 C1 O1 179.7(7) . . . . ?
C4 N1 C1 C2 1.5(11) . . . . ?
C3 N2 C2 C12 -100.9(8) . . . . ?
C3 N2 C2 C1 19.2(9) . . . . ?
C3 N2 C2 S1 141.7(6) . . . . ?
O1 C1 C2 N2 164.4(7) . . . . ?
N1 C1 C2 N2 -17.4(9) . . . . ?
O1 C1 C2 C12 -74.1(8) . . . . ?
N1 C1 C2 C12 104.2(7) . . . . ?
O1 C1 C2 S1 42.3(9) . . . . ?
N1 C1 C2 S1 -139.5(6) . . . . ?
C19 S1 C2 N2 -61.1(5) . . . . ?
C19 S1 C2 C12 179.0(5) . . . . ?
C19 S1 C2 C1 61.7(6) . . . . ?
C2 N2 C3 O2 174.8(6) . . . . ?
C2 N2 C3 C4 -3.4(11) . . . . ?
C1 N1 C4 C5 -162.9(7) . . . . ?
C1 N1 C4 C3 15.2(10) . . . . ?
O2 C3 C4 C5 -14.3(10) . . . . ?
N2 C3 C4 C5 163.9(7) . . . . ?
O2 C3 C4 N1 167.6(7) . . . . ?
N2 C3 C4 N1 -14.3(9) . . . . ?
N1 C4 C5 C6 4.9(12) . . . . ?
C3 C4 C5 C6 -173.1(7) . . . . ?
C4 C5 C6 C7 -144.1(8) . . . . ?
C4 C5 C6 C11 41.4(12) . . . . ?
C11 C6 C7 O3 166(6) . . . . ?
C5 C6 C7 O3 -9(6) . . . . ?
C11 C6 C7 C8 -2.3(12) . . . . ?
C5 C6 C7 C8 -177.1(7) . . . . ?
C11 C6 C7 O3' -161(9) . . . . ?
C5 C6 C7 O3' 24(9) . . . . ?
O3 C7 C8 C9 -166(7) . . . . ?
C6 C7 C8 C9 1.4(12) . . . . ?
O3' C7 C8 C9 160(9) . . . . ?
C7 C8 C9 C10 0.2(11) . . . . ?
C8 C9 C10 C11 -0.7(11) . . . . ?
C9 C10 C11 C6 -0.2(10) . . . . ?
C7 C6 C11 C10 1.7(10) . . . . ?
C5 C6 C11 C10 176.3(6) . . . . ?
N2 C2 C12 C13 62.7(8) . . . . ?
C1 C2 C12 C13 -59.1(7) . . . . ?
S1 C2 C12 C13 -177.9(5) . . . . ?
C2 C12 C13 C14 94.4(8) . . . . ?
C2 C12 C13 C18 -86.7(8) . . . . ?
C18 C13 C14 C15 0.4(11) . . . . ?
C12 C13 C14 C15 179.4(7) . . . . ?
C13 C14 C15 C16 1.3(12) . . . . ?
C14 C15 C16 C17 -1.1(13) . . . . ?
C15 C16 C17 C18 -0.9(14) . . . . ?
C14 C13 C18 C17 -2.4(11) . . . . ?
C12 C13 C18 C17 178.6(7) . . . . ?
C16 C17 C18 C13 2.7(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        66.18
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.054
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_150503f
_database_code_depnum_ccdc_archive 'CCDC 1541035'
_audit_update_record             
;
2017-11-27 deposited with the CCDC.
2017-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H15 N O3'
_chemical_formula_weight         233.26

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'
O O 0.0492 0.0322 '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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   9.5217(8)
_cell_length_b                   9.7711(11)
_cell_length_c                   12.4273(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1156.20(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1188
_cell_measurement_theta_min      4.5330
_cell_measurement_theta_max      71.5000

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7195
_exptl_absorpt_correction_T_max  0.8528
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2384
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         5.76
_diffrn_reflns_theta_max         66.14
_reflns_number_total             1665
_reflns_number_gt                1450
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_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)+(0.0543P)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   0.0(4)
_chemical_absolute_configuration R/S
_refine_ls_number_reflns         1665
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1048
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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
N1 N 0.2012(2) 0.4464(2) 0.09601(16) 0.0421(5) Uani 1 1 d . . .
O1 O 0.0206(2) 0.38147(19) 0.20666(15) 0.0550(5) Uani 1 1 d . . .
O2 O -0.0807(2) 0.6514(2) 0.17352(16) 0.0595(6) Uani 1 1 d . . .
H2 H -0.0858 0.7187 0.2128 0.089 Uiso 1 1 calc R . .
O3 O -0.2221(2) 0.6089(4) -0.32896(16) 0.0874(9) Uani 1 1 d . . .
H3 H -0.2919 0.5620 -0.3173 0.131 Uiso 1 1 calc R . .
C1 C 0.0897(3) 0.4676(3) 0.15631(17) 0.0411(6) Uani 1 1 d . . .
C2 C 0.0608(3) 0.6216(3) 0.1525(2) 0.0453(6) Uani 1 1 d . . .
H2A H 0.1179 0.6657 0.2082 0.054 Uiso 1 1 calc R . .
C3 C 0.1201(3) 0.6637(2) 0.0413(2) 0.0420(6) Uani 1 1 d . . .
H3A H 0.1514 0.7592 0.0444 0.050 Uiso 1 1 calc R . .
C4 C 0.2506(3) 0.5685(3) 0.0387(2) 0.0433(6) Uani 1 1 d . . .
H4 H 0.3267 0.6110 0.0800 0.052 Uiso 1 1 calc R . .
C5 C 0.3107(3) 0.5072(3) -0.0638(2) 0.0589(8) Uani 1 1 d . . .
H5A H 0.3827 0.5655 -0.0946 0.071 Uiso 1 1 calc R . .
H5B H 0.2379 0.4913 -0.1169 0.071 Uiso 1 1 calc R . .
C6 C 0.3728(3) 0.3721(3) -0.0227(3) 0.0669(9) Uani 1 1 d . . .
H6A H 0.3849 0.3075 -0.0813 0.080 Uiso 1 1 calc R . .
H6B H 0.4630 0.3873 0.0116 0.080 Uiso 1 1 calc R . .
C7 C 0.2649(3) 0.3198(3) 0.0583(2) 0.0558(7) Uani 1 1 d . . .
H7A H 0.1962 0.2608 0.0241 0.067 Uiso 1 1 calc R . .
H7B H 0.3097 0.2705 0.1167 0.067 Uiso 1 1 calc R . .
C8 C 0.0234(3) 0.6456(2) -0.0536(2) 0.0412(6) Uani 1 1 d . . .
C9 C -0.0856(3) 0.5518(3) -0.0579(2) 0.0464(6) Uani 1 1 d . . .
H9 H -0.1033 0.4969 0.0017 0.056 Uiso 1 1 calc R . .
C10 C -0.1688(3) 0.5377(3) -0.1483(2) 0.0490(7) Uani 1 1 d . . .
H10 H -0.2413 0.4739 -0.1490 0.059 Uiso 1 1 calc R . .
C11 C -0.1441(3) 0.6183(4) -0.2378(2) 0.0542(8) Uani 1 1 d . . .
C12 C -0.0373(3) 0.7140(3) -0.2348(2) 0.0578(8) Uani 1 1 d . . .
H12 H -0.0210 0.7699 -0.2940 0.069 Uiso 1 1 calc R . .
C13 C 0.0448(3) 0.7265(3) -0.1444(2) 0.0513(7) Uani 1 1 d . . .
H13 H 0.1167 0.7909 -0.1438 0.062 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
N1 C1 1.316(3) . ?
N1 C7 1.455(3) . ?
N1 C4 1.467(3) . ?
O1 C1 1.238(3) . ?
O2 C2 1.403(3) . ?
O2 H2 0.8200 . ?
O3 C11 1.358(3) . ?
O3 H3 0.8200 . ?
C1 C2 1.530(4) . ?
C2 C3 1.549(3) . ?
C2 H2A 0.9800 . ?
C3 C8 1.506(4) . ?
C3 C4 1.552(4) . ?
C3 H3A 0.9800 . ?
C4 C5 1.519(4) . ?
C4 H4 0.9800 . ?
C5 C6 1.533(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.527(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.386(3) . ?
C8 C13 1.393(3) . ?
C9 C10 1.382(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.383(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.382(4) . ?
C12 C13 1.375(4) . ?
C12 H12 0.9300 . ?
C13 H13 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
C1 N1 C7 130.8(2) . . ?
C1 N1 C4 114.1(2) . . ?
C7 N1 C4 113.6(2) . . ?
C2 O2 H2 109.5 . . ?
C11 O3 H3 109.5 . . ?
O1 C1 N1 127.6(3) . . ?
O1 C1 C2 126.0(2) . . ?
N1 C1 C2 106.4(2) . . ?
O2 C2 C1 111.8(2) . . ?
O2 C2 C3 117.5(2) . . ?
C1 C2 C3 102.9(2) . . ?
O2 C2 H2A 108.1 . . ?
C1 C2 H2A 108.1 . . ?
C3 C2 H2A 108.1 . . ?
C8 C3 C2 116.4(2) . . ?
C8 C3 C4 113.8(2) . . ?
C2 C3 C4 98.7(2) . . ?
C8 C3 H3A 109.2 . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3A 109.2 . . ?
N1 C4 C5 102.0(2) . . ?
N1 C4 C3 102.71(18) . . ?
C5 C4 C3 123.7(2) . . ?
N1 C4 H4 109.1 . . ?
C5 C4 H4 109.1 . . ?
C3 C4 H4 109.1 . . ?
C4 C5 C6 101.9(2) . . ?
C4 C5 H5A 111.4 . . ?
C6 C5 H5A 111.4 . . ?
C4 C5 H5B 111.4 . . ?
C6 C5 H5B 111.4 . . ?
H5A C5 H5B 109.3 . . ?
C7 C6 C5 104.4(2) . . ?
C7 C6 H6A 110.9 . . ?
C5 C6 H6A 110.9 . . ?
C7 C6 H6B 110.9 . . ?
C5 C6 H6B 110.9 . . ?
H6A C6 H6B 108.9 . . ?
N1 C7 C6 102.0(2) . . ?
N1 C7 H7A 111.4 . . ?
C6 C7 H7A 111.4 . . ?
N1 C7 H7B 111.4 . . ?
C6 C7 H7B 111.4 . . ?
H7A C7 H7B 109.2 . . ?
C9 C8 C13 117.0(2) . . ?
C9 C8 C3 124.5(2) . . ?
C13 C8 C3 118.6(2) . . ?
C10 C9 C8 121.8(2) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C9 C10 C11 120.0(3) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
O3 C11 C12 118.1(3) . . ?
O3 C11 C10 122.7(3) . . ?
C12 C11 C10 119.3(3) . . ?
C13 C12 C11 120.1(2) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C8 121.9(3) . . ?
C12 C13 H13 119.0 . . ?
C8 C13 H13 119.0 . . ?

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
C7 N1 C1 O1 9.4(4) . . . . ?
C4 N1 C1 O1 174.3(2) . . . . ?
C7 N1 C1 C2 -170.6(3) . . . . ?
C4 N1 C1 C2 -5.7(3) . . . . ?
O1 C1 C2 O2 -24.8(4) . . . . ?
N1 C1 C2 O2 155.2(2) . . . . ?
O1 C1 C2 C3 -151.7(2) . . . . ?
N1 C1 C2 C3 28.2(3) . . . . ?
O2 C2 C3 C8 -38.5(3) . . . . ?
C1 C2 C3 C8 84.7(3) . . . . ?
O2 C2 C3 C4 -160.6(2) . . . . ?
C1 C2 C3 C4 -37.3(2) . . . . ?
C1 N1 C4 C5 -148.2(2) . . . . ?
C7 N1 C4 C5 19.4(3) . . . . ?
C1 N1 C4 C3 -19.1(3) . . . . ?
C7 N1 C4 C3 148.4(2) . . . . ?
C8 C3 C4 N1 -90.0(2) . . . . ?
C2 C3 C4 N1 34.0(2) . . . . ?
C8 C3 C4 C5 24.0(3) . . . . ?
C2 C3 C4 C5 147.9(2) . . . . ?
N1 C4 C5 C6 -35.4(3) . . . . ?
C3 C4 C5 C6 -149.7(2) . . . . ?
C4 C5 C6 C7 40.1(3) . . . . ?
C1 N1 C7 C6 170.3(2) . . . . ?
C4 N1 C7 C6 5.3(3) . . . . ?
C5 C6 C7 N1 -28.0(3) . . . . ?
C2 C3 C8 C9 -25.7(4) . . . . ?
C4 C3 C8 C9 88.1(3) . . . . ?
C2 C3 C8 C13 155.3(2) . . . . ?
C4 C3 C8 C13 -91.0(3) . . . . ?
C13 C8 C9 C10 0.7(4) . . . . ?
C3 C8 C9 C10 -178.4(2) . . . . ?
C8 C9 C10 C11 0.0(4) . . . . ?
C9 C10 C11 O3 179.9(3) . . . . ?
C9 C10 C11 C12 -1.0(4) . . . . ?
O3 C11 C12 C13 -179.6(3) . . . . ?
C10 C11 C12 C13 1.2(4) . . . . ?
C11 C12 C13 C8 -0.5(4) . . . . ?
C9 C8 C13 C12 -0.5(4) . . . . ?
C3 C8 C13 C12 178.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        66.14
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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_160109b
_database_code_depnum_ccdc_archive 'CCDC 1541033'
_audit_update_record             
;
2017-11-27 deposited with the CCDC.
2017-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 N2 O4 S'
_chemical_formula_weight         384.43

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'
O O 0.0492 0.0322 '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'
S S 0.3331 0.5567 '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)

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

_cell_length_a                   8.2444(4)
_cell_length_b                   9.9359(4)
_cell_length_c                   11.8715(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.077(3)
_cell_angle_gamma                90.00
_cell_volume                     913.37(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3394
_cell_measurement_theta_min      7.3410
_cell_measurement_theta_max      71.7330

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.34
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             402
_exptl_absorpt_coefficient_mu    1.827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5436
_exptl_absorpt_correction_T_max  0.5755
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5774
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0399
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.96
_diffrn_reflns_theta_max         66.44
_reflns_number_total             2457
_reflns_number_gt                2340
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_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)+(0.0733P)²+0.0186P] 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     SHELXL
_refine_ls_extinction_coef       0.0204(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(2)
_chemical_absolute_configuration R/S
_refine_ls_number_reflns         2457
_refine_ls_number_parameters     247
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1070
_refine_ls_wR_factor_gt          0.1053
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.060
_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
N1 N 0.4558(3) 0.5353(2) 0.28295(19) 0.0286(5) Uani 1 1 d . . .
N2 N 0.4700(3) 0.7975(3) 0.3672(2) 0.0351(6) Uani 1 1 d . . .
O1 O 0.6311(3) 0.4681(2) 0.46678(17) 0.0401(5) Uani 1 1 d . . .
O2 O 0.2290(3) 0.8477(2) 0.20999(19) 0.0434(5) Uani 1 1 d . . .
O3 O 0.6048(3) 0.2479(3) 0.3471(2) 0.0526(6) Uani 1 1 d . . .
H3 H 0.6368 0.3125 0.3923 0.079 Uiso 1 1 calc R . .
O4 O 0.9639(5) 0.0444(4) 0.2015(4) 0.0999(12) Uani 1 1 d . . .
H4 H 1.0508 -0.0021 0.2153 0.150 Uiso 1 1 calc R . .
S1 S 0.52492(8) 0.67971(8) 0.11655(6) 0.0366(2) Uani 1 1 d . . .
C1 C 0.5627(4) 0.5602(3) 0.3956(2) 0.0324(6) Uani 1 1 d . . .
C2 C 0.5979(3) 0.7030(3) 0.4297(2) 0.0314(6) Uani 1 1 d . . .
C3 C 0.3491(3) 0.7707(3) 0.2588(2) 0.0307(6) Uani 1 1 d . . .
C4 C 0.3743(3) 0.6437(3) 0.1974(2) 0.0285(6) Uani 1 1 d . . .
C5 C 0.2051(4) 0.5788(3) 0.1157(3) 0.0339(6) Uani 1 1 d . . .
H5A H 0.1095 0.6011 0.1423 0.041 Uiso 1 1 calc R . .
H5B H 0.1776 0.6077 0.0332 0.041 Uiso 1 1 calc R . .
C6 C 0.2440(3) 0.4314(3) 0.1285(3) 0.0349(6) Uani 1 1 d . . .
C7 C 0.3917(4) 0.4078(3) 0.2285(2) 0.0308(6) Uani 1 1 d . . .
C8 C 0.4561(4) 0.2791(3) 0.2581(3) 0.0368(6) Uani 1 1 d . . .
C9 C 0.3645(4) 0.1737(4) 0.1867(3) 0.0476(7) Uani 1 1 d . . .
H9 H 0.4031 0.0858 0.2055 0.057 Uiso 1 1 calc R . .
C10 C 0.2184(4) 0.1968(4) 0.0891(3) 0.0523(8) Uani 1 1 d . . .
H10 H 0.1603 0.1243 0.0433 0.063 Uiso 1 1 calc R . .
C11 C 0.1557(4) 0.3262(4) 0.0574(3) 0.0435(8) Uani 1 1 d . . .
H11 H 0.0576 0.3416 -0.0093 0.052 Uiso 1 1 calc R . .
C12 C 0.7448(4) 0.7327(3) 0.5202(2) 0.0354(6) Uani 1 1 d . . .
H12 H 0.8039 0.6571 0.5597 0.042 Uiso 1 1 calc R . .
C13 C 0.8304(3) 0.8593(3) 0.5691(2) 0.0340(6) Uani 1 1 d . . .
C14 C 0.7811(4) 0.9869(4) 0.5204(3) 0.0411(7) Uani 1 1 d . . .
H14 H 0.6808 0.9968 0.4542 0.049 Uiso 1 1 calc R . .
C15 C 0.8800(4) 1.0992(4) 0.5698(3) 0.0470(8) Uani 1 1 d . . .
H15 H 0.8458 1.1835 0.5359 0.056 Uiso 1 1 calc R . .
C16 C 1.0291(4) 1.0869(4) 0.6689(3) 0.0447(8) Uani 1 1 d . . .
H16 H 1.0951 1.1624 0.7017 0.054 Uiso 1 1 calc R . .
C17 C 1.0781(4) 0.9621(4) 0.7178(3) 0.0517(9) Uani 1 1 d . . .
H17 H 1.1779 0.9532 0.7846 0.062 Uiso 1 1 calc R . .
C18 C 0.9809(4) 0.8495(4) 0.6692(3) 0.0453(8) Uani 1 1 d . . .
H18 H 1.0164 0.7657 0.7039 0.054 Uiso 1 1 calc R . .
C19 C 0.4060(6) 0.8026(4) 0.0080(4) 0.0605(11) Uani 1 1 d . . .
H19A H 0.3053 0.7612 -0.0480 0.091 Uiso 1 1 calc R . .
H19B H 0.4778 0.8372 -0.0341 0.091 Uiso 1 1 calc R . .
H19C H 0.3715 0.8751 0.0484 0.091 Uiso 1 1 calc R . .
C20 C 0.8473(10) -0.0215(8) 0.2361(7) 0.121(2) Uani 1 1 d . . .
H20A H 0.9009 -0.0533 0.3168 0.182 Uiso 1 1 calc R . .
H20B H 0.8031 -0.0966 0.1837 0.182 Uiso 1 1 calc R . .
H20C H 0.7541 0.0382 0.2327 0.182 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
N1 C1 1.348(4) . ?
N1 C7 1.438(4) . ?
N1 C4 1.474(3) . ?
N2 C3 1.356(4) . ?
N2 C2 1.417(4) . ?
O1 C1 1.242(4) . ?
O2 C3 1.228(4) . ?
O3 C8 1.352(4) . ?
O3 H3 0.8200 . ?
O4 C20 1.340(7) . ?
O4 H4 0.8200 . ?
S1 C19 1.801(4) . ?
S1 C4 1.847(3) . ?
C1 C2 1.477(4) . ?
C2 C12 1.348(4) . ?
C3 C4 1.506(4) . ?
C4 C5 1.541(4) . ?
C5 C6 1.496(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C11 1.383(4) . ?
C6 C7 1.397(4) . ?
C7 C8 1.383(4) . ?
C8 C9 1.396(5) . ?
C9 C10 1.374(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.388(5) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.461(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.395(5) . ?
C13 C18 1.397(4) . ?
C14 C15 1.387(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.385(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.370(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.382(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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 N1 C7 128.5(2) . . ?
C1 N1 C4 122.5(2) . . ?
C7 N1 C4 108.9(2) . . ?
C3 N2 C2 122.6(2) . . ?
C8 O3 H3 109.5 . . ?
C20 O4 H4 109.5 . . ?
C19 S1 C4 101.84(15) . . ?
O1 C1 N1 122.0(3) . . ?
O1 C1 C2 121.4(2) . . ?
N1 C1 C2 116.6(2) . . ?
C12 C2 N2 125.2(3) . . ?
C12 C2 C1 117.9(3) . . ?
N2 C2 C1 116.9(2) . . ?
O2 C3 N2 122.4(3) . . ?
O2 C3 C4 121.1(2) . . ?
N2 C3 C4 116.4(2) . . ?
N1 C4 C3 112.6(2) . . ?
N1 C4 C5 103.2(2) . . ?
C3 C4 C5 114.2(2) . . ?
N1 C4 S1 105.71(17) . . ?
C3 C4 S1 108.5(2) . . ?
C5 C4 S1 112.24(18) . . ?
C6 C5 C4 103.3(2) . . ?
C6 C5 H5A 111.1 . . ?
C4 C5 H5A 111.1 . . ?
C6 C5 H5B 111.1 . . ?
C4 C5 H5B 111.1 . . ?
H5A C5 H5B 109.1 . . ?
C11 C6 C7 121.0(3) . . ?
C11 C6 C5 128.9(3) . . ?
C7 C6 C5 110.1(3) . . ?
C8 C7 C6 121.1(3) . . ?
C8 C7 N1 130.6(2) . . ?
C6 C7 N1 108.2(3) . . ?
O3 C8 C7 125.3(3) . . ?
O3 C8 C9 117.3(3) . . ?
C7 C8 C9 117.3(3) . . ?
C10 C9 C8 121.4(3) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C11 121.4(3) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C6 C11 C10 117.7(3) . . ?
C6 C11 H11 121.1 . . ?
C10 C11 H11 121.1 . . ?
C2 C12 C13 133.2(3) . . ?
C2 C12 H12 113.4 . . ?
C13 C12 H12 113.4 . . ?
C14 C13 C18 117.6(3) . . ?
C14 C13 C12 125.9(2) . . ?
C18 C13 C12 116.4(3) . . ?
C15 C14 C13 120.7(3) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C16 C15 C14 120.6(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 119.1(3) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C16 C17 C18 120.8(3) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C17 C18 C13 121.1(3) . . ?
C17 C18 H18 119.4 . . ?
C13 C18 H18 119.4 . . ?
S1 C19 H19A 109.5 . . ?
S1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
S1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 C1 O1 5.2(4) . . . . ?
C4 N1 C1 O1 -179.8(3) . . . . ?
C7 N1 C1 C2 -176.0(3) . . . . ?
C4 N1 C1 C2 -1.0(4) . . . . ?
C3 N2 C2 C12 162.3(3) . . . . ?
C3 N2 C2 C1 -20.4(4) . . . . ?
O1 C1 C2 C12 22.3(4) . . . . ?
N1 C1 C2 C12 -156.5(2) . . . . ?
O1 C1 C2 N2 -155.3(3) . . . . ?
N1 C1 C2 N2 26.0(4) . . . . ?
C2 N2 C3 O2 173.1(3) . . . . ?
C2 N2 C3 C4 -9.9(4) . . . . ?
C1 N1 C4 C3 -27.9(3) . . . . ?
C7 N1 C4 C3 148.0(2) . . . . ?
C1 N1 C4 C5 -151.5(2) . . . . ?
C7 N1 C4 C5 24.3(3) . . . . ?
C1 N1 C4 S1 90.5(3) . . . . ?
C7 N1 C4 S1 -93.7(2) . . . . ?
O2 C3 C4 N1 -150.0(3) . . . . ?
N2 C3 C4 N1 32.9(3) . . . . ?
O2 C3 C4 C5 -32.7(4) . . . . ?
N2 C3 C4 C5 150.2(2) . . . . ?
O2 C3 C4 S1 93.3(3) . . . . ?
N2 C3 C4 S1 -83.8(3) . . . . ?
C19 S1 C4 N1 175.8(2) . . . . ?
C19 S1 C4 C3 -63.2(2) . . . . ?
C19 S1 C4 C5 64.0(3) . . . . ?
N1 C4 C5 C6 -23.5(3) . . . . ?
C3 C4 C5 C6 -146.1(2) . . . . ?
S1 C4 C5 C6 89.8(2) . . . . ?
C4 C5 C6 C11 -164.4(3) . . . . ?
C4 C5 C6 C7 15.6(3) . . . . ?
C11 C6 C7 C8 1.3(4) . . . . ?
C5 C6 C7 C8 -178.7(3) . . . . ?
C11 C6 C7 N1 179.2(3) . . . . ?
C5 C6 C7 N1 -0.8(3) . . . . ?
C1 N1 C7 C8 -22.3(4) . . . . ?
C4 N1 C7 C8 162.2(3) . . . . ?
C1 N1 C7 C6 160.1(3) . . . . ?
C4 N1 C7 C6 -15.4(3) . . . . ?
C6 C7 C8 O3 174.7(3) . . . . ?
N1 C7 C8 O3 -2.7(5) . . . . ?
C6 C7 C8 C9 -2.2(4) . . . . ?
N1 C7 C8 C9 -179.5(3) . . . . ?
O3 C8 C9 C10 -175.5(3) . . . . ?
C7 C8 C9 C10 1.6(5) . . . . ?
C8 C9 C10 C11 -0.1(5) . . . . ?
C7 C6 C11 C10 0.3(5) . . . . ?
C5 C6 C11 C10 -179.7(3) . . . . ?
C9 C10 C11 C6 -0.9(5) . . . . ?
N2 C2 C12 C13 -10.4(5) . . . . ?
C1 C2 C12 C13 172.2(3) . . . . ?
C2 C12 C13 C14 -6.9(5) . . . . ?
C2 C12 C13 C18 177.2(3) . . . . ?
C18 C13 C14 C15 0.7(5) . . . . ?
C12 C13 C14 C15 -175.2(3) . . . . ?
C13 C14 C15 C16 -0.5(5) . . . . ?
C14 C15 C16 C17 0.0(5) . . . . ?
C15 C16 C17 C18 0.2(5) . . . . ?
C16 C17 C18 C13 0.0(6) . . . . ?
C14 C13 C18 C17 -0.5(5) . . . . ?
C12 C13 C18 C17 175.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        66.44
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_150503d
_database_code_depnum_ccdc_archive 'CCDC 1541034'
_audit_update_record             
;
2017-11-27 deposited with the CCDC.
2017-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H25 N O6 S'
_chemical_formula_weight         383.45

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   5.6325(5)
_cell_length_b                   7.9186(7)
_cell_length_c                   10.9501(9)
_cell_angle_alpha                88.389(2)
_cell_angle_beta                 83.8230(10)
_cell_angle_gamma                87.401(2)
_cell_volume                     484.92(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    761
_cell_measurement_theta_min      3.9970
_cell_measurement_theta_max      70.6160

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             204
_exptl_absorpt_coefficient_mu    1.774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5300
_exptl_absorpt_correction_T_max  0.7893
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2610
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0559
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.06
_diffrn_reflns_theta_max         65.95
_reflns_number_total             1878
_reflns_number_gt                1483
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_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)+(0.0973P)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   0.02(7)
_chemical_absolute_configuration R/S
_refine_ls_number_reflns         1878
_refine_ls_number_parameters     239
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_ref         0.1779
_refine_ls_wR_factor_gt          0.1553
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.071
_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
N1 N 0.3467(11) 0.7161(7) 0.7116(5) 0.0534(13) Uani 1 1 d . . .
O1 O 0.6071(11) 0.6950(7) 0.8595(5) 0.0790(17) Uani 1 1 d . . .
O2 O 0.8484(8) 0.4394(6) 0.7231(4) 0.0595(12) Uani 1 1 d . . .
H2 H 0.9403 0.4852 0.6704 0.071 Uiso 1 1 calc R . .
O3 O 0.7740(8) 0.6450(6) 0.5321(4) 0.0524(11) Uani 1 1 d . . .
H3 H 0.7828 0.6679 0.4583 0.063 Uiso 1 1 calc R . .
O4 O 0.5554(11) 0.0068(6) 0.2305(4) 0.0683(14) Uani 1 1 d . . .
H4 H 0.6724 -0.0583 0.2326 0.103 Uiso 1 1 calc R . .
O5 O 0.2834(18) 0.3687(11) 0.9456(7) 0.130(3) Uani 1 1 d . . .
O6 O 0.8532(11) 0.7471(7) 0.2856(4) 0.0724(16) Uani 1 1 d . . .
S1 S 1.0095(4) 0.6422(3) 0.19343(18) 0.0733(6) Uani 1 1 d . . .
C1 C 0.5254(13) 0.6429(9) 0.7706(6) 0.0554(17) Uani 1 1 d . . .
C2 C 0.6099(12) 0.4833(9) 0.7019(6) 0.0470(14) Uani 1 1 d . . .
C3 C 0.5769(11) 0.5403(8) 0.5651(6) 0.0452(14) Uani 1 1 d . . .
C4 C 0.3401(11) 0.6498(8) 0.5860(6) 0.0468(14) Uani 1 1 d . . .
H4A H 0.2020 0.5793 0.5840 0.056 Uiso 1 1 calc R . .
C5 C 0.3095(13) 0.8116(9) 0.5095(6) 0.0538(16) Uani 1 1 d . . .
H5A H 0.4634 0.8551 0.4788 0.065 Uiso 1 1 calc R . .
H5B H 0.2206 0.7921 0.4405 0.065 Uiso 1 1 calc R . .
C6 C 0.1718(19) 0.9326(11) 0.5983(8) 0.077(2) Uani 1 1 d . . .
H6A H 0.0014 0.9186 0.5994 0.092 Uiso 1 1 calc R . .
H6B H 0.2055 1.0485 0.5739 0.092 Uiso 1 1 calc R . .
C7 C 0.2509(18) 0.8920(10) 0.7244(8) 0.075(2) Uani 1 1 d . . .
H7A H 0.3732 0.9668 0.7431 0.090 Uiso 1 1 calc R . .
H7B H 0.1173 0.9001 0.7880 0.090 Uiso 1 1 calc R . .
C8 C 0.4567(13) 0.3318(8) 0.7420(6) 0.0538(16) Uani 1 1 d . . .
H8A H 0.2968 0.3536 0.7185 0.065 Uiso 1 1 calc R . .
H8B H 0.5248 0.2320 0.6997 0.065 Uiso 1 1 calc R . .
C9 C 0.4424(17) 0.2981(10) 0.8802(7) 0.070(2) Uani 1 1 d . . .
C10 C 0.622(2) 0.1783(12) 0.9291(8) 0.096(3) Uani 1 1 d . . .
H10A H 0.6081 0.1838 1.0170 0.144 Uiso 1 1 calc R . .
H10B H 0.7797 0.2083 0.8959 0.144 Uiso 1 1 calc R . .
H10C H 0.5943 0.0655 0.9059 0.144 Uiso 1 1 calc R . .
C11 C 0.5685(11) 0.4008(8) 0.4754(5) 0.0447(14) Uani 1 1 d . . .
C12 C 0.7554(12) 0.2761(9) 0.4628(7) 0.0540(16) Uani 1 1 d . . .
H12 H 0.8818 0.2816 0.5104 0.065 Uiso 1 1 calc R . .
C13 C 0.7553(13) 0.1476(9) 0.3825(7) 0.0560(17) Uani 1 1 d . . .
H13 H 0.8822 0.0678 0.3762 0.067 Uiso 1 1 calc R . .
C14 C 0.5685(13) 0.1329(8) 0.3095(6) 0.0525(16) Uani 1 1 d . . .
C15 C 0.3876(13) 0.2582(9) 0.3190(6) 0.0551(16) Uani 1 1 d . . .
H15 H 0.2635 0.2546 0.2697 0.066 Uiso 1 1 calc R . .
C16 C 0.3883(12) 0.3880(9) 0.4004(6) 0.0532(16) Uani 1 1 d . . .
H16 H 0.2636 0.4694 0.4049 0.064 Uiso 1 1 calc R . .
C17 C 1.112(2) 0.7862(15) 0.0743(11) 0.112(4) Uani 1 1 d . . .
H17A H 0.9779 0.8360 0.0372 0.167 Uiso 1 1 calc R . .
H17B H 1.2170 0.7270 0.0134 0.167 Uiso 1 1 calc R . .
H17C H 1.1968 0.8733 0.1080 0.167 Uiso 1 1 calc R . .
C18 C 0.816(3) 0.5311(18) 0.1136(11) 0.117(4) Uani 1 1 d . . .
H18A H 0.7419 0.4459 0.1669 0.175 Uiso 1 1 calc R . .
H18B H 0.9047 0.4786 0.0439 0.175 Uiso 1 1 calc R . .
H18C H 0.6950 0.6080 0.0860 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
N1 C1 1.354(9) . ?
N1 C7 1.476(9) . ?
N1 C4 1.491(8) . ?
O1 C1 1.210(9) . ?
O2 C2 1.415(8) . ?
O2 H2 0.8200 . ?
O3 C3 1.425(7) . ?
O3 H3 0.8200 . ?
O4 C14 1.349(8) . ?
O4 H4 0.8200 . ?
O5 C9 1.211(11) . ?
O6 S1 1.508(6) . ?
S1 C18 1.750(13) . ?
S1 C17 1.774(11) . ?
C1 C2 1.520(10) . ?
C2 C8 1.536(9) . ?
C2 C3 1.579(8) . ?
C3 C11 1.505(9) . ?
C3 C4 1.557(9) . ?
C4 C5 1.525(9) . ?
C4 H4A 0.9800 . ?
C5 C6 1.513(11) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.518(12) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.523(10) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.487(14) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C16 1.382(9) . ?
C11 C12 1.408(9) . ?
C12 C13 1.364(10) . ?
C12 H12 0.9300 . ?
C13 C14 1.399(10) . ?
C13 H13 0.9300 . ?
C14 C15 1.387(10) . ?
C15 C16 1.380(9) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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 N1 C7 126.3(6) . . ?
C1 N1 C4 112.9(5) . . ?
C7 N1 C4 113.3(5) . . ?
C2 O2 H2 109.5 . . ?
C3 O3 H3 109.5 . . ?
C14 O4 H4 109.5 . . ?
O6 S1 C18 106.3(5) . . ?
O6 S1 C17 105.5(4) . . ?
C18 S1 C17 98.7(6) . . ?
O1 C1 N1 127.1(7) . . ?
O1 C1 C2 126.1(7) . . ?
N1 C1 C2 106.8(5) . . ?
O2 C2 C1 109.6(5) . . ?
O2 C2 C8 107.9(5) . . ?
C1 C2 C8 112.7(6) . . ?
O2 C2 C3 114.5(5) . . ?
C1 C2 C3 101.3(5) . . ?
C8 C2 C3 110.8(5) . . ?
O3 C3 C11 111.8(5) . . ?
O3 C3 C4 110.5(5) . . ?
C11 C3 C4 113.8(5) . . ?
O3 C3 C2 103.2(5) . . ?
C11 C3 C2 116.2(5) . . ?
C4 C3 C2 100.3(5) . . ?
N1 C4 C5 102.2(5) . . ?
N1 C4 C3 103.2(5) . . ?
C5 C4 C3 119.5(6) . . ?
N1 C4 H4A 110.4 . . ?
C5 C4 H4A 110.4 . . ?
C3 C4 H4A 110.4 . . ?
C6 C5 C4 104.0(6) . . ?
C6 C5 H5A 111.0 . . ?
C4 C5 H5A 111.0 . . ?
C6 C5 H5B 111.0 . . ?
C4 C5 H5B 111.0 . . ?
H5A C5 H5B 109.0 . . ?
C5 C6 C7 107.2(7) . . ?
C5 C6 H6A 110.3 . . ?
C7 C6 H6A 110.3 . . ?
C5 C6 H6B 110.3 . . ?
C7 C6 H6B 110.3 . . ?
H6A C6 H6B 108.5 . . ?
N1 C7 C6 102.3(6) . . ?
N1 C7 H7A 111.3 . . ?
C6 C7 H7A 111.3 . . ?
N1 C7 H7B 111.3 . . ?
C6 C7 H7B 111.3 . . ?
H7A C7 H7B 109.2 . . ?
C9 C8 C2 111.9(6) . . ?
C9 C8 H8A 109.2 . . ?
C2 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C2 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
O5 C9 C10 122.7(8) . . ?
O5 C9 C8 118.6(8) . . ?
C10 C9 C8 118.7(7) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C11 C12 116.5(6) . . ?
C16 C11 C3 123.8(6) . . ?
C12 C11 C3 119.6(6) . . ?
C13 C12 C11 121.6(6) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C14 121.5(6) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
O4 C14 C15 118.6(6) . . ?
O4 C14 C13 124.3(6) . . ?
C15 C14 C13 117.1(6) . . ?
C16 C15 C14 121.2(6) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C11 122.0(7) . . ?
C15 C16 H16 119.0 . . ?
C11 C16 H16 119.0 . . ?
S1 C17 H17A 109.5 . . ?
S1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
S1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
S1 C18 H18A 109.5 . . ?
S1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
S1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 C1 O1 15.0(12) . . . . ?
C4 N1 C1 O1 162.3(7) . . . . ?
C7 N1 C1 C2 -163.6(7) . . . . ?
C4 N1 C1 C2 -16.2(7) . . . . ?
O1 C1 C2 O2 -22.8(9) . . . . ?
N1 C1 C2 O2 155.8(5) . . . . ?
O1 C1 C2 C8 97.4(8) . . . . ?
N1 C1 C2 C8 -84.0(6) . . . . ?
O1 C1 C2 C3 -144.1(7) . . . . ?
N1 C1 C2 C3 34.5(6) . . . . ?
O2 C2 C3 O3 -41.9(7) . . . . ?
C1 C2 C3 O3 75.9(6) . . . . ?
C8 C2 C3 O3 -164.3(5) . . . . ?
O2 C2 C3 C11 80.9(7) . . . . ?
C1 C2 C3 C11 -161.3(5) . . . . ?
C8 C2 C3 C11 -41.5(8) . . . . ?
O2 C2 C3 C4 -156.0(5) . . . . ?
C1 C2 C3 C4 -38.2(6) . . . . ?
C8 C2 C3 C4 81.6(6) . . . . ?
C1 N1 C4 C5 -134.0(6) . . . . ?
C7 N1 C4 C5 17.7(8) . . . . ?
C1 N1 C4 C3 -9.4(7) . . . . ?
C7 N1 C4 C3 142.3(6) . . . . ?
O3 C3 C4 N1 -79.1(6) . . . . ?
C11 C3 C4 N1 154.1(5) . . . . ?
C2 C3 C4 N1 29.3(6) . . . . ?
O3 C3 C4 C5 33.3(8) . . . . ?
C11 C3 C4 C5 -93.5(7) . . . . ?
C2 C3 C4 C5 141.7(6) . . . . ?
N1 C4 C5 C6 -30.1(7) . . . . ?
C3 C4 C5 C6 -143.0(7) . . . . ?
C4 C5 C6 C7 33.4(9) . . . . ?
C1 N1 C7 C6 149.4(7) . . . . ?
C4 N1 C7 C6 2.2(10) . . . . ?
C5 C6 C7 N1 -21.9(10) . . . . ?
O2 C2 C8 C9 66.2(7) . . . . ?
C1 C2 C8 C9 -54.9(8) . . . . ?
C3 C2 C8 C9 -167.7(6) . . . . ?
C2 C8 C9 O5 89.5(10) . . . . ?
C2 C8 C9 C10 -91.3(9) . . . . ?
O3 C3 C11 C16 -114.4(6) . . . . ?
C4 C3 C11 C16 11.7(8) . . . . ?
C2 C3 C11 C16 127.5(6) . . . . ?
O3 C3 C11 C12 64.1(7) . . . . ?
C4 C3 C11 C12 -169.9(5) . . . . ?
C2 C3 C11 C12 -54.1(8) . . . . ?
C16 C11 C12 C13 -1.3(9) . . . . ?
C3 C11 C12 C13 -179.9(6) . . . . ?
C11 C12 C13 C14 -0.4(10) . . . . ?
C12 C13 C14 O4 -178.4(6) . . . . ?
C12 C13 C14 C15 2.2(10) . . . . ?
O4 C14 C15 C16 178.4(6) . . . . ?
C13 C14 C15 C16 -2.2(10) . . . . ?
C14 C15 C16 C11 0.5(10) . . . . ?
C12 C11 C16 C15 1.3(9) . . . . ?
C3 C11 C16 C15 179.8(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        65.95
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.075
