# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_exp_4697
_database_code_depnum_ccdc_archive 'CCDC 1522074'
_audit_update_record             
;
2016-12-12 deposited with the CCDC.
2017-06-19 downloaded from the CCDC.
;
_audit_creation_date             2016-12-12
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H19 N O5 S'
_chemical_formula_sum            'C22 H19 N O5 S'
_chemical_formula_weight         409.44
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   8.8173(4)
_cell_length_b                   14.3926(7)
_cell_length_c                   15.3659(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1950.00(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4140
_cell_measurement_temperature    105.8
_cell_measurement_theta_max      70.8098
_cell_measurement_theta_min      4.2053
_exptl_absorpt_coefficient_mu    1.775
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.23
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6453
_diffrn_reflns_theta_full        70.95
_diffrn_reflns_theta_max         70.95
_diffrn_reflns_theta_min         4.21
_diffrn_ambient_temperature      105.8
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -76.00  -51.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000    0.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega   12.00   38.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000    0.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -35.00   -9.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  111.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  -29.00   45.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -56.0000   97.0000 74

#__ type_ start__ end____ width___ exp.time_
  5 omega   59.00   89.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919 -123.0000   44.0000 30

#__ type_ start__ end____ width___ exp.time_
  6 omega   20.00   80.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919 -123.0000 -135.0000 60

#__ type_ start__ end____ width___ exp.time_
  7 omega   19.00   65.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   37.0000  150.0000 46

#__ type_ start__ end____ width___ exp.time_
  8 omega   34.00   76.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919 -148.0000   60.0000 42

#__ type_ start__ end____ width___ exp.time_
  9 omega  108.00  170.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  150.0000 62

#__ type_ start__ end____ width___ exp.time_
 10 omega  115.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  150.0000 63

#__ type_ start__ end____ width___ exp.time_
 11 omega   63.00   89.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega   91.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -150.0000 85

#__ type_ start__ end____ width___ exp.time_
 13 omega   82.00  175.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 93

#__ type_ start__ end____ width___ exp.time_
 14 omega   91.00  137.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 46

#__ type_ start__ end____ width___ exp.time_
 15 omega  120.00  166.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  123.0000  -44.0000 46
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0168200000
_diffrn_orient_matrix_UB_12      0.0797775000
_diffrn_orient_matrix_UB_13      0.0661894000
_diffrn_orient_matrix_UB_21      -0.1732397000
_diffrn_orient_matrix_UB_22      0.0013106000
_diffrn_orient_matrix_UB_23      0.0130355000
_diffrn_orient_matrix_UB_31      0.0154465000
_diffrn_orient_matrix_UB_32      -0.0713978000
_diffrn_orient_matrix_UB_33      0.0741141000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3629
_reflns_number_total             3678
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.003(12)
_refine_ls_extinction_coef       0.0059(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3678
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0271
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0373P)²+0.2919P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0689
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.02160(4) 0.89742(2) 0.86919(2) 0.01158(10) Uani 1 1 d . . .
O4 O -0.08686(13) 0.70418(8) 0.62467(7) 0.0172(2) Uani 1 1 d . . .
O3 O -0.00920(14) 0.85324(8) 0.62950(8) 0.0216(3) Uani 1 1 d . . .
O2 O 0.09174(14) 0.87865(9) 0.95120(8) 0.0213(3) Uani 1 1 d . . .
C4 C -0.28292(18) 0.85831(11) 0.91461(9) 0.0110(3) Uani 1 1 d . . .
O1 O 0.01486(14) 0.99298(7) 0.84225(8) 0.0177(2) Uani 1 1 d . . .
C20 C 0.46668(19) 0.56575(11) 0.69177(10) 0.0150(3) Uani 1 1 d . . .
H20 H 0.4937 0.6115 0.6519 0.018 Uiso 1 1 calc R . .
O5 O 0.26034(15) 0.71082(8) 0.66289(9) 0.0230(3) Uani 1 1 d . . .
C18 C 0.5235(2) 0.42291(11) 0.76618(11) 0.0185(3) Uani 1 1 d . . .
H18 H 0.5889 0.3734 0.7766 0.022 Uiso 1 1 calc R . .
C8 C -0.29877(19) 0.93804(11) 0.96820(10) 0.0148(3) Uani 1 1 d . . .
H8 H -0.2180 0.9790 0.9751 0.018 Uiso 1 1 calc R . .
C12 C -0.02724(19) 0.77816(10) 0.66262(10) 0.0146(3) Uani 1 1 d . . .
C9 C -0.4333(2) 0.95434(13) 1.00964(11) 0.0192(4) Uani 1 1 d . . .
H9 H -0.4443 1.0074 1.0436 0.023 Uiso 1 1 calc R . .
C16 C 0.28834(19) 0.50215(11) 0.79425(10) 0.0156(3) Uani 1 1 d . . .
H16 H 0.1957 0.5051 0.8231 0.019 Uiso 1 1 calc R . .
C3 C -0.15207(17) 0.83824(10) 0.86447(10) 0.0102(3) Uani 1 1 d . . .
C11 C -0.54148(19) 0.81365(12) 0.95182(10) 0.0170(3) Uani 1 1 d . . .
H11 H -0.6223 0.7724 0.9477 0.020 Uiso 1 1 calc R . .
C5 C -0.40520(18) 0.79490(11) 0.90641(10) 0.0127(3) Uani 1 1 d . . .
C14 C 0.22933(18) 0.65403(10) 0.71882(10) 0.0128(3) Uani 1 1 d . . .
C10 C -0.55542(18) 0.89184(13) 1.00168(10) 0.0187(4) Uani 1 1 d . . .
H10 H -0.6461 0.9038 1.0305 0.022 Uiso 1 1 calc R . .
C13 C 0.08740(18) 0.66547(10) 0.77391(10) 0.0115(3) Uani 1 1 d . . .
H13A H 0.1145 0.6599 0.8349 0.014 Uiso 1 1 calc R . .
H13B H 0.0170 0.6158 0.7602 0.014 Uiso 1 1 calc R . .
C19 C 0.56352(18) 0.49186(12) 0.70707(11) 0.0171(3) Uani 1 1 d . . .
H19 H 0.6556 0.4883 0.6777 0.021 Uiso 1 1 calc R . .
C7 C -0.26194(18) 0.70064(10) 0.80304(10) 0.0139(3) Uani 1 1 d . . .
H7 H -0.2552 0.6492 0.7666 0.017 Uiso 1 1 calc R . .
N1 N 0.10385(16) 0.83600(9) 0.79060(10) 0.0168(3) Uani 1 1 d . . .
H1 H 0.1260 0.8731 0.7486 0.020 Uiso 1 1 d R . .
C15 C 0.32866(18) 0.57203(11) 0.73587(10) 0.0121(3) Uani 1 1 d . . .
C21 C -0.1272(2) 0.71542(13) 0.53275(11) 0.0240(4) Uani 1 1 d . . .
H21A H -0.0375 0.7296 0.4987 0.029 Uiso 1 1 calc R . .
H21B H -0.1991 0.7659 0.5259 0.029 Uiso 1 1 calc R . .
C1 C 0.00864(18) 0.75883(10) 0.75933(10) 0.0123(3) Uani 1 1 d . . .
C6 C -0.38953(19) 0.71610(11) 0.85151(10) 0.0145(3) Uani 1 1 d . . .
H6 H -0.4687 0.6736 0.8484 0.017 Uiso 1 1 calc R . .
C17 C 0.3855(2) 0.42830(12) 0.80959(11) 0.0190(4) Uani 1 1 d . . .
H17 H 0.3582 0.3822 0.8490 0.023 Uiso 1 1 calc R . .
C2 C -0.14065(17) 0.76439(10) 0.80950(10) 0.0109(3) Uani 1 1 d . . .
C22 C -0.1958(3) 0.62644(14) 0.50280(12) 0.0300(4) Uani 1 1 d . . .
H22A H -0.2233 0.6316 0.4425 0.045 Uiso 1 1 calc R . .
H22B H -0.2847 0.6133 0.5367 0.045 Uiso 1 1 calc R . .
H22C H -0.1237 0.5770 0.5098 0.045 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4295(12) . ?
S1 O1 1.4376(11) . ?
S1 C3 1.7537(15) . ?
S1 N1 1.6630(14) . ?
O4 C12 1.323(2) . ?
O4 C21 1.465(2) . ?
O3 C12 1.2051(19) . ?
C4 C8 1.419(2) . ?
C4 C3 1.417(2) . ?
C4 C5 1.418(2) . ?
C20 H20 0.9300 . ?
C20 C19 1.384(2) . ?
C20 C15 1.396(2) . ?
O5 C14 1.217(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.391(2) . ?
C18 C17 1.390(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.366(2) . ?
C12 C1 1.545(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.409(3) . ?
C16 H16 0.9300 . ?
C16 C15 1.394(2) . ?
C16 C17 1.385(2) . ?
C3 C2 1.361(2) . ?
C11 H11 0.9300 . ?
C11 C5 1.415(2) . ?
C11 C10 1.367(2) . ?
C5 C6 1.420(2) . ?
C14 C13 1.520(2) . ?
C14 C15 1.493(2) . ?
C10 H10 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C1 1.529(2) . ?
C19 H19 0.9300 . ?
C7 H7 0.9300 . ?
C7 C6 1.367(2) . ?
C7 C2 1.413(2) . ?
N1 H1 0.8599 . ?
N1 C1 1.473(2) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.489(3) . ?
C1 C2 1.528(2) . ?
C6 H6 0.9300 . ?
C17 H17 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
O2 S1 O1 116.91(7) . . ?
O2 S1 C3 108.81(7) . . ?
O2 S1 N1 110.55(8) . . ?
O1 S1 C3 114.63(7) . . ?
O1 S1 N1 108.51(7) . . ?
N1 S1 C3 95.32(7) . . ?
C12 O4 C21 115.63(13) . . ?
C3 C4 C8 124.09(15) . . ?
C3 C4 C5 116.07(13) . . ?
C5 C4 C8 119.81(15) . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C15 120.35(15) . . ?
C15 C20 H20 119.8 . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C17 C18 C19 119.71(15) . . ?
C4 C8 H8 120.2 . . ?
C9 C8 C4 119.65(16) . . ?
C9 C8 H8 120.2 . . ?
O4 C12 C1 111.14(13) . . ?
O3 C12 O4 126.01(15) . . ?
O3 C12 C1 122.74(15) . . ?
C8 C9 H9 119.5 . . ?
C8 C9 C10 120.90(16) . . ?
C10 C9 H9 119.5 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C17 C16 C15 120.36(16) . . ?
C4 C3 S1 126.11(12) . . ?
C2 C3 S1 109.89(12) . . ?
C2 C3 C4 123.83(14) . . ?
C5 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C5 120.64(16) . . ?
C4 C5 C6 119.52(15) . . ?
C11 C5 C4 118.61(15) . . ?
C11 C5 C6 121.85(15) . . ?
O5 C14 C13 120.37(14) . . ?
O5 C14 C15 121.53(15) . . ?
C15 C14 C13 118.10(13) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.37(15) . . ?
C11 C10 H10 119.8 . . ?
C14 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C14 C13 C1 112.80(12) . . ?
H13A C13 H13B 107.8 . . ?
C1 C13 H13A 109.0 . . ?
C1 C13 H13B 109.0 . . ?
C20 C19 C18 120.18(15) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C6 C7 H7 120.7 . . ?
C6 C7 C2 118.61(14) . . ?
C2 C7 H7 120.7 . . ?
S1 N1 H1 108.3 . . ?
C1 N1 S1 112.90(10) . . ?
C1 N1 H1 110.7 . . ?
C20 C15 C14 118.52(14) . . ?
C16 C15 C20 119.22(15) . . ?
C16 C15 C14 122.26(14) . . ?
O4 C21 H21A 110.2 . . ?
O4 C21 H21B 110.2 . . ?
O4 C21 C22 107.55(14) . . ?
H21A C21 H21B 108.5 . . ?
C22 C21 H21A 110.2 . . ?
C22 C21 H21B 110.2 . . ?
C13 C1 C12 113.09(12) . . ?
N1 C1 C12 107.14(13) . . ?
N1 C1 C13 110.86(13) . . ?
N1 C1 C2 106.68(12) . . ?
C2 C1 C12 107.43(13) . . ?
C2 C1 C13 111.31(12) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 C5 122.24(15) . . ?
C7 C6 H6 118.9 . . ?
C18 C17 H17 119.9 . . ?
C16 C17 C18 120.17(16) . . ?
C16 C17 H17 119.9 . . ?
C3 C2 C7 119.65(14) . . ?
C3 C2 C1 114.69(13) . . ?
C7 C2 C1 125.66(13) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
S1 C3 C2 C7 172.99(12) . . . . ?
S1 C3 C2 C1 -6.84(16) . . . . ?
S1 N1 C1 C12 116.95(12) . . . . ?
S1 N1 C1 C13 -119.22(12) . . . . ?
S1 N1 C1 C2 2.13(15) . . . . ?
O4 C12 C1 C13 45.29(18) . . . . ?
O4 C12 C1 N1 167.74(13) . . . . ?
O4 C12 C1 C2 -77.95(15) . . . . ?
O3 C12 C1 C13 -138.32(16) . . . . ?
O3 C12 C1 N1 -15.9(2) . . . . ?
O3 C12 C1 C2 98.45(18) . . . . ?
O2 S1 C3 C4 68.64(15) . . . . ?
O2 S1 C3 C2 -106.83(12) . . . . ?
O2 S1 N1 C1 107.20(12) . . . . ?
C4 C8 C9 C10 1.6(2) . . . . ?
C4 C3 C2 C7 -2.6(2) . . . . ?
C4 C3 C2 C1 177.57(13) . . . . ?
C4 C5 C6 C7 -2.6(2) . . . . ?
O1 S1 C3 C4 -64.37(15) . . . . ?
O1 S1 C3 C2 120.17(11) . . . . ?
O1 S1 N1 C1 -123.37(12) . . . . ?
O5 C14 C13 C1 -8.1(2) . . . . ?
O5 C14 C15 C20 5.9(2) . . . . ?
O5 C14 C15 C16 -174.28(16) . . . . ?
C8 C4 C3 S1 8.9(2) . . . . ?
C8 C4 C3 C2 -176.23(15) . . . . ?
C8 C4 C5 C11 0.6(2) . . . . ?
C8 C4 C5 C6 178.92(14) . . . . ?
C8 C9 C10 C11 -0.3(2) . . . . ?
C12 O4 C21 C22 -178.42(15) . . . . ?
C12 C1 C2 C3 -111.38(14) . . . . ?
C12 C1 C2 C7 68.80(18) . . . . ?
C3 S1 N1 C1 -5.18(12) . . . . ?
C3 C4 C8 C9 175.75(15) . . . . ?
C3 C4 C5 C11 -177.12(14) . . . . ?
C3 C4 C5 C6 1.2(2) . . . . ?
C11 C5 C6 C7 175.67(15) . . . . ?
C5 C4 C8 C9 -1.7(2) . . . . ?
C5 C4 C3 S1 -173.53(11) . . . . ?
C5 C4 C3 C2 1.3(2) . . . . ?
C5 C11 C10 C9 -0.9(2) . . . . ?
C14 C13 C1 C12 53.90(18) . . . . ?
C14 C13 C1 N1 -66.46(16) . . . . ?
C14 C13 C1 C2 174.96(13) . . . . ?
C10 C11 C5 C4 0.8(2) . . . . ?
C10 C11 C5 C6 -177.55(15) . . . . ?
C13 C14 C15 C20 -173.72(14) . . . . ?
C13 C14 C15 C16 6.1(2) . . . . ?
C13 C1 C2 C3 124.30(14) . . . . ?
C13 C1 C2 C7 -55.5(2) . . . . ?
C19 C20 C15 C16 -1.2(2) . . . . ?
C19 C20 C15 C14 178.64(14) . . . . ?
C19 C18 C17 C16 -0.2(2) . . . . ?
N1 S1 C3 C4 -177.53(13) . . . . ?
N1 S1 C3 C2 7.00(12) . . . . ?
N1 C1 C2 C3 3.24(18) . . . . ?
N1 C1 C2 C7 -176.58(14) . . . . ?
C15 C20 C19 C18 0.4(2) . . . . ?
C15 C16 C17 C18 -0.6(2) . . . . ?
C15 C14 C13 C1 171.55(13) . . . . ?
C21 O4 C12 O3 3.0(2) . . . . ?
C21 O4 C12 C1 179.20(14) . . . . ?
C6 C7 C2 C3 1.2(2) . . . . ?
C6 C7 C2 C1 -179.02(14) . . . . ?
C17 C18 C19 C20 0.3(2) . . . . ?
C17 C16 C15 C20 1.3(2) . . . . ?
C17 C16 C15 C14 -178.54(15) . . . . ?
C2 C7 C6 C5 1.4(2) . . . . ?

####################################################################### 
# 
# 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_exp_4772
_database_code_depnum_ccdc_archive 'CCDC 1536298'
_audit_update_record             
;
2017-03-04 deposited with the CCDC.
2017-06-19 downloaded from the CCDC.
;
_audit_creation_date             2017-02-24
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H23 N O5 S'
_chemical_formula_sum            'C21 H23 N O5 S'
_chemical_formula_weight         401.46
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.2203(5)
_cell_length_b                   9.1263(5)
_cell_length_c                   13.0906(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.302(6)
_cell_angle_gamma                90
_cell_volume                     959.52(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3417
_cell_measurement_temperature    106.3
_cell_measurement_theta_max      71.2262
_cell_measurement_theta_min      4.8416
_exptl_absorpt_coefficient_mu    1.785
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6248
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.367
_diffrn_reflns_theta_min         5.508
_diffrn_ambient_temperature      106.3
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -64.00  -23.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000    0.0000 -150.0000 41

#__ type_ start__ end____ width___ exp.time_
  2 omega   30.00   56.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000    0.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega   72.00   99.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   70.0000  -10.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega  -32.00   40.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000  -30.0000 72

#__ type_ start__ end____ width___ exp.time_
  5 omega   79.00  104.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega    0.00   73.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919 -103.0000  -50.0000 73

#__ type_ start__ end____ width___ exp.time_
  7 omega   10.00  102.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000   90.0000 92

#__ type_ start__ end____ width___ exp.time_
  8 omega   71.00  105.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   37.0000  150.0000 34

#__ type_ start__ end____ width___ exp.time_
  9 omega  -30.00   36.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000 -150.0000 66

#__ type_ start__ end____ width___ exp.time_
 10 omega   28.00   68.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000    0.0000 40

#__ type_ start__ end____ width___ exp.time_
 11 omega  100.00  143.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000 -120.0000 43

#__ type_ start__ end____ width___ exp.time_
 12 omega   97.00  134.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  150.0000 37

#__ type_ start__ end____ width___ exp.time_
 13 omega  121.00  178.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -90.0000 57

#__ type_ start__ end____ width___ exp.time_
 14 omega   56.00   98.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 42

#__ type_ start__ end____ width___ exp.time_
 15 omega   40.00   82.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 42

#__ type_ start__ end____ width___ exp.time_
 16 omega   50.00   98.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 48

#__ type_ start__ end____ width___ exp.time_
 17 omega   42.00   96.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000 -120.0000 54

#__ type_ start__ end____ width___ exp.time_
 18 omega   61.00   96.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 35

#__ type_ start__ end____ width___ exp.time_
 19 omega   80.00  106.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -103.0000  -50.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   58.00   98.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   30.0000 40

#__ type_ start__ end____ width___ exp.time_
 21 omega   70.00  157.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -60.0000 87

#__ type_ start__ end____ width___ exp.time_
 22 omega  150.00  176.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 23 omega   72.00  122.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -180.0000 50

#__ type_ start__ end____ width___ exp.time_
 24 omega  113.00  138.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 25 omega   75.00  104.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -120.0000 29

#__ type_ start__ end____ width___ exp.time_
 26 omega   44.00   83.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 39

#__ type_ start__ end____ width___ exp.time_
 27 omega   38.00  107.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -103.0000   -2.0000 69

#__ type_ start__ end____ width___ exp.time_
 28 omega   83.00  167.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 84

#__ type_ start__ end____ width___ exp.time_
 29 omega   70.00  116.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -114.0000  150.0000 46
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0282451000
_diffrn_orient_matrix_UB_12      -0.1622148000
_diffrn_orient_matrix_UB_13      0.0240259000
_diffrn_orient_matrix_UB_21      0.1529478000
_diffrn_orient_matrix_UB_22      0.0041036000
_diffrn_orient_matrix_UB_23      0.0915207000
_diffrn_orient_matrix_UB_31      -0.1125456000
_diffrn_orient_matrix_UB_32      0.0470339000
_diffrn_orient_matrix_UB_33      0.0742713000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.841
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.942
_reflns_number_gt                3525
_reflns_number_total             3588
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Flack x determined using 1559 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3588
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0678P)²+0.0517P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.0986
_refine_special_details          ?
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.13678(8) 0.31598(7) 0.90134(5) 0.01778(18) Uani 1 1 d . . . . .
O1 O -0.3799(3) 0.0962(2) 0.61780(16) 0.0243(5) Uani 1 1 d . . . . .
O4 O 0.2968(3) 0.3307(3) 0.8740(2) 0.0334(6) Uani 1 1 d . . . . .
O2 O -0.0406(3) -0.0203(2) 0.65075(16) 0.0232(5) Uani 1 1 d . . . . .
C17 C -0.4767(3) -0.1824(4) 0.7948(2) 0.0165(5) Uani 1 1 d . . . . .
H17 H -0.4039 -0.1559 0.8587 0.020 Uiso 1 1 calc R U . . .
C5 C -0.0168(4) 0.5715(3) 0.8150(2) 0.0195(6) Uani 1 1 d . . . . .
H5 H 0.0657 0.6284 0.8597 0.023 Uiso 1 1 calc R U . . .
O5 O 0.1333(3) 0.3409(3) 1.00922(17) 0.0308(6) Uani 1 1 d . . . . .
O3 O 0.0421(3) 0.2120(2) 0.63355(16) 0.0196(4) Uani 1 1 d . . . . .
C3 C -0.1321(3) 0.3307(3) 0.75800(19) 0.0141(5) Uani 1 1 d . . . . .
C16 C -0.4767(3) -0.1012(3) 0.7039(2) 0.0157(6) Uani 1 1 d . . . . .
N1 N 0.0483(3) 0.1563(3) 0.86303(18) 0.0146(5) Uani 1 1 d . . . . .
C7 C -0.2653(4) 0.5497(3) 0.6814(2) 0.0206(6) Uani 1 1 d . . . . .
H7 H -0.3536 0.5957 0.6334 0.025 Uiso 1 1 calc R U . . .
C1 C -0.2378(3) 0.0715(3) 0.7966(2) 0.0136(5) Uani 1 1 d . . . . .
H1 H -0.1862 -0.0205 0.8304 0.016 Uiso 1 1 calc R U . . .
C19 C -0.6872(4) -0.3433(4) 0.6986(3) 0.0258(7) Uani 1 1 d . . . . .
H19 H -0.7587 -0.4254 0.6970 0.031 Uiso 1 1 calc R U . . .
C2 C -0.0956(3) 0.1676(3) 0.7713(2) 0.0132(5) Uani 1 1 d . . . . .
C9 C -0.0329(3) 0.1071(3) 0.6758(2) 0.0142(5) Uani 1 1 d . . . . .
C12 C 0.1627(4) 0.0302(3) 0.8700(2) 0.0185(6) Uani 1 1 d . . . . .
H12A H 0.2359 0.0444 0.8197 0.022 Uiso 1 1 calc R U . . .
H12B H 0.0968 -0.0600 0.8497 0.022 Uiso 1 1 calc R U . . .
C13 C 0.2701(4) 0.0103(4) 0.9793(2) 0.0231(6) Uani 1 1 d . . . . .
H13A H 0.3413 -0.0760 0.9802 0.035 Uiso 1 1 calc R U . . .
H13B H 0.1983 -0.0032 1.0294 0.035 Uiso 1 1 calc R U . . .
H13C H 0.3398 0.0973 0.9984 0.035 Uiso 1 1 calc R U . . .
C8 C -0.2619(4) 0.3975(3) 0.6881(2) 0.0183(6) Uani 1 1 d . . . . .
H8 H -0.3467 0.3403 0.6457 0.022 Uiso 1 1 calc R U . . .
C6 C -0.1435(4) 0.6365(3) 0.7427(2) 0.0221(6) Uani 1 1 d . . . . .
H6 H -0.1473 0.7401 0.7349 0.026 Uiso 1 1 calc R U . . .
C4 C -0.0154(4) 0.4197(3) 0.8197(2) 0.0158(6) Uani 1 1 d . . . . .
C14 C -0.3225(4) 0.1492(3) 0.8757(2) 0.0176(6) Uani 1 1 d . . . . .
H14A H -0.2372 0.1879 0.9334 0.026 Uiso 1 1 calc R U . . .
H14B H -0.3928 0.0792 0.9032 0.026 Uiso 1 1 calc R U . . .
H14C H -0.3913 0.2300 0.8410 0.026 Uiso 1 1 calc R U . . .
C21 C -0.5829(4) -0.1447(3) 0.6107(2) 0.0184(6) Uani 1 1 d . . . . .
H21 H -0.5837 -0.0911 0.5484 0.022 Uiso 1 1 calc R U . . .
C20 C -0.6868(4) -0.2647(4) 0.6077(2) 0.0249(7) Uani 1 1 d . . . . .
H20 H -0.7576 -0.2933 0.5436 0.030 Uiso 1 1 calc R U . . .
C18 C -0.5824(4) -0.3012(4) 0.7918(2) 0.0216(6) Uani 1 1 d . . . . .
H18 H -0.5834 -0.3543 0.8540 0.026 Uiso 1 1 calc R U . . .
C11 C 0.2611(4) 0.2896(4) 0.5550(3) 0.0274(7) Uani 1 1 d . . . . .
H11A H 0.3255 0.2681 0.5019 0.041 Uiso 1 1 calc R U . . .
H11B H 0.3365 0.2964 0.6238 0.041 Uiso 1 1 calc R U . . .
H11C H 0.2023 0.3829 0.5385 0.041 Uiso 1 1 calc R U . . .
C10 C 0.1380(4) 0.1702(4) 0.5564(2) 0.0253(7) Uani 1 1 d . . . . .
H10A H 0.0639 0.1593 0.4866 0.030 Uiso 1 1 calc R U . . .
H10B H 0.1959 0.0760 0.5760 0.030 Uiso 1 1 calc R U . . .
C15 C -0.3662(3) 0.0273(3) 0.6995(2) 0.0155(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O4 1.441(2) . ?
S1 O5 1.437(2) . ?
S1 N1 1.658(2) . ?
S1 C4 1.742(3) . ?
O1 C15 1.225(3) . ?
O2 C9 1.206(4) . ?
C17 H17 0.9500 . ?
C17 C16 1.402(4) . ?
C17 C18 1.385(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.384(4) . ?
C5 C4 1.387(4) . ?
O3 C9 1.322(4) . ?
O3 C10 1.458(3) . ?
C3 C2 1.521(4) . ?
C3 C8 1.390(4) . ?
C3 C4 1.379(4) . ?
C16 C21 1.398(4) . ?
C16 C15 1.492(4) . ?
N1 C2 1.499(3) . ?
N1 C12 1.477(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.392(4) . ?
C7 C6 1.390(5) . ?
C1 H1 1.0000 . ?
C1 C2 1.553(4) . ?
C1 C14 1.538(4) . ?
C1 C15 1.523(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.390(5) . ?
C19 C18 1.389(4) . ?
C2 C9 1.552(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.523(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C8 H8 0.9500 . ?
C6 H6 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C21 H21 0.9500 . ?
C21 C20 1.384(4) . ?
C20 H20 0.9500 . ?
C18 H18 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11 C10 1.489(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?

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 N1 111.82(13) . . ?
O4 S1 C4 111.75(14) . . ?
O5 S1 O4 116.11(15) . . ?
O5 S1 N1 109.69(14) . . ?
O5 S1 C4 110.82(14) . . ?
N1 S1 C4 94.63(13) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C18 C17 C16 120.2(3) . . ?
C6 C5 H5 121.4 . . ?
C6 C5 C4 117.2(3) . . ?
C4 C5 H5 121.4 . . ?
C9 O3 C10 118.0(2) . . ?
C8 C3 C2 127.6(3) . . ?
C4 C3 C2 114.4(2) . . ?
C4 C3 C8 117.9(3) . . ?
C17 C16 C15 123.9(3) . . ?
C21 C16 C17 118.6(3) . . ?
C21 C16 C15 117.5(3) . . ?
C2 N1 S1 113.72(18) . . ?
C12 N1 S1 115.71(19) . . ?
C12 N1 C2 119.1(2) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C6 C7 C8 122.0(3) . . ?
C2 C1 H1 107.5 . . ?
C14 C1 H1 107.5 . . ?
C14 C1 C2 110.6(2) . . ?
C15 C1 H1 107.5 . . ?
C15 C1 C2 113.0(2) . . ?
C15 C1 C14 110.6(2) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C18 C19 C20 119.6(3) . . ?
C3 C2 C1 116.0(2) . . ?
C3 C2 C9 110.3(2) . . ?
N1 C2 C3 105.2(2) . . ?
N1 C2 C1 107.0(2) . . ?
N1 C2 C9 106.2(2) . . ?
C9 C2 C1 111.4(2) . . ?
O2 C9 O3 125.9(3) . . ?
O2 C9 C2 123.7(3) . . ?
O3 C9 C2 110.1(2) . . ?
N1 C12 H12A 109.1 . . ?
N1 C12 H12B 109.1 . . ?
N1 C12 C13 112.6(2) . . ?
H12A C12 H12B 107.8 . . ?
C13 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C3 C8 C7 118.8(3) . . ?
C3 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C5 C6 C7 119.7(3) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C5 C4 S1 124.6(2) . . ?
C3 C4 S1 111.0(2) . . ?
C3 C4 C5 124.4(3) . . ?
C1 C14 H14A 109.5 . . ?
C1 C14 H14B 109.5 . . ?
C1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C21 H21 119.5 . . ?
C20 C21 C16 121.1(3) . . ?
C20 C21 H21 119.5 . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.9(3) . . ?
C21 C20 H20 120.1 . . ?
C17 C18 C19 120.7(3) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
O3 C10 C11 106.6(2) . . ?
O3 C10 H10A 110.4 . . ?
O3 C10 H10B 110.4 . . ?
C11 C10 H10A 110.4 . . ?
C11 C10 H10B 110.4 . . ?
H10A C10 H10B 108.6 . . ?
O1 C15 C16 119.6(3) . . ?
O1 C15 C1 120.8(3) . . ?
C16 C15 C1 119.7(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C2 C3 -10.8(3) . . . . ?
S1 N1 C2 C1 -134.74(19) . . . . ?
S1 N1 C2 C9 106.2(2) . . . . ?
S1 N1 C12 C13 55.1(3) . . . . ?
O4 S1 N1 C2 -107.2(2) . . . . ?
O4 S1 N1 C12 36.1(2) . . . . ?
O4 S1 C4 C5 -65.7(3) . . . . ?
O4 S1 C4 C3 112.7(2) . . . . ?
C17 C16 C21 C20 0.4(4) . . . . ?
C17 C16 C15 O1 -176.6(3) . . . . ?
C17 C16 C15 C1 3.3(4) . . . . ?
O5 S1 N1 C2 122.5(2) . . . . ?
O5 S1 N1 C12 -94.2(2) . . . . ?
O5 S1 C4 C5 65.5(3) . . . . ?
O5 S1 C4 C3 -116.1(2) . . . . ?
C3 C2 C9 O2 -157.7(3) . . . . ?
C3 C2 C9 O3 27.9(3) . . . . ?
C16 C17 C18 C19 1.4(5) . . . . ?
C16 C21 C20 C19 0.4(5) . . . . ?
N1 S1 C4 C5 178.6(3) . . . . ?
N1 S1 C4 C3 -3.0(2) . . . . ?
N1 C2 C9 O2 88.8(3) . . . . ?
N1 C2 C9 O3 -85.5(3) . . . . ?
C1 C2 C9 O2 -27.4(4) . . . . ?
C1 C2 C9 O3 158.3(2) . . . . ?
C2 C3 C8 C7 -174.2(3) . . . . ?
C2 C3 C4 S1 -3.2(3) . . . . ?
C2 C3 C4 C5 175.2(3) . . . . ?
C2 N1 C12 C13 -163.6(2) . . . . ?
C2 C1 C15 O1 -20.2(4) . . . . ?
C2 C1 C15 C16 159.9(2) . . . . ?
C9 O3 C10 C11 -157.0(3) . . . . ?
C12 N1 C2 C3 -152.8(2) . . . . ?
C12 N1 C2 C1 83.3(3) . . . . ?
C12 N1 C2 C9 -35.8(3) . . . . ?
C8 C3 C2 N1 -175.1(3) . . . . ?
C8 C3 C2 C1 -57.1(4) . . . . ?
C8 C3 C2 C9 70.7(3) . . . . ?
C8 C3 C4 S1 -179.8(2) . . . . ?
C8 C3 C4 C5 -1.4(4) . . . . ?
C8 C7 C6 C5 -1.9(5) . . . . ?
C6 C5 C4 S1 177.5(2) . . . . ?
C6 C5 C4 C3 -0.7(4) . . . . ?
C6 C7 C8 C3 -0.3(5) . . . . ?
C4 S1 N1 C2 8.4(2) . . . . ?
C4 S1 N1 C12 151.7(2) . . . . ?
C4 C5 C6 C7 2.3(4) . . . . ?
C4 C3 C2 N1 8.6(3) . . . . ?
C4 C3 C2 C1 126.6(2) . . . . ?
C4 C3 C2 C9 -105.5(3) . . . . ?
C4 C3 C8 C7 1.9(4) . . . . ?
C14 C1 C2 C3 -41.0(3) . . . . ?
C14 C1 C2 N1 76.0(3) . . . . ?
C14 C1 C2 C9 -168.3(2) . . . . ?
C14 C1 C15 O1 104.4(3) . . . . ?
C14 C1 C15 C16 -75.5(3) . . . . ?
C21 C16 C15 O1 5.3(4) . . . . ?
C21 C16 C15 C1 -174.9(2) . . . . ?
C20 C19 C18 C17 -0.5(5) . . . . ?
C18 C17 C16 C21 -1.3(4) . . . . ?
C18 C17 C16 C15 -179.4(3) . . . . ?
C18 C19 C20 C21 -0.4(5) . . . . ?
C10 O3 C9 O2 -6.2(5) . . . . ?
C10 O3 C9 C2 168.0(2) . . . . ?
C15 C16 C21 C20 178.6(3) . . . . ?
C15 C1 C2 C3 83.6(3) . . . . ?
C15 C1 C2 N1 -159.4(2) . . . . ?
C15 C1 C2 C9 -43.7(3) . . . . ?

_shelx_estimated_absorpt_T_max   0.788
_shelx_estimated_absorpt_T_min   0.414
_shelx_SHELXL_version_number     2014/7
_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.
;
