# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_1
_audit_block_doi                 10.5517/cc12gx9r
_database_code_depnum_ccdc_archive 'CCDC 997434'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/ja504818p 2014
_audit_update_record             
;
2014-10-07 deposited with the CCDC.
2017-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H23 N O2 S'
_chemical_formula_weight         389.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   11.7831(5)
_cell_length_b                   9.6543(4)
_cell_length_c                   17.6007(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.297(2)
_cell_angle_gamma                90.00
_cell_volume                     1990.13(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9988
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      29.84

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9473
_exptl_absorpt_correction_T_max  0.9576
_exptl_absorpt_process_details   'SADABS (Sheldrick, V2.10)'

_exptl_special_details           
; 
  'Blessing, Acta Cryst. (1995) A51, 33-38'  
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            81204
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0118
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         30.01
_reflns_number_total             5822
_reflns_number_gt                4736
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0668P)²+0.4005P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5822
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1294
_refine_ls_wR_factor_gt          0.1183
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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 0.33568(3) 0.24243(4) 0.86362(2) 0.04669(11) Uani 1 1 d . . .
O1 O 0.31339(9) 0.30531(13) 0.93394(6) 0.0647(3) Uani 1 1 d . . .
O2 O 0.41950(9) 0.30103(13) 0.82017(8) 0.0672(3) Uani 1 1 d . . .
C1 C -0.20942(11) 0.21136(15) 0.81491(8) 0.0471(3) Uani 1 1 d . . .
C2 C -0.28346(12) 0.28785(19) 0.85566(9) 0.0592(4) Uani 1 1 d . . .
H2 H -0.3611 0.2676 0.8491 0.071 Uiso 1 1 calc R . .
C3 C -0.24463(14) 0.39239(19) 0.90525(9) 0.0627(4) Uani 1 1 d . . .
H3 H -0.2963 0.4413 0.9312 0.075 Uiso 1 1 calc R . .
C4 C -0.13027(13) 0.42534(16) 0.91683(8) 0.0530(3) Uani 1 1 d . . .
H4 H -0.1041 0.4945 0.9511 0.064 Uiso 1 1 calc R . .
C5 C -0.05496(10) 0.35284(13) 0.87603(6) 0.0398(2) Uani 1 1 d . . .
C6 C 0.07199(11) 0.36943(14) 0.87845(7) 0.0442(3) Uani 1 1 d . . .
H6A H 0.1074 0.3812 0.9305 0.053 Uiso 1 1 calc R . .
H6B H 0.0915 0.4477 0.8479 0.053 Uiso 1 1 calc R . .
C7 C 0.10788(9) 0.23203(12) 0.84422(6) 0.0351(2) Uani 1 1 d . . .
H7 H 0.1180 0.1625 0.8850 0.042 Uiso 1 1 calc R . .
N8 N 0.21510(8) 0.24271(11) 0.80807(6) 0.0402(2) Uani 1 1 d . . .
C9 C 0.21570(11) 0.17713(16) 0.73242(7) 0.0457(3) Uani 1 1 d . . .
H9A H 0.2055 0.0778 0.7366 0.055 Uiso 1 1 calc R . .
H9B H 0.2881 0.1942 0.7126 0.055 Uiso 1 1 calc R . .
C10 C 0.12002(11) 0.23796(13) 0.67985(7) 0.0401(2) Uani 1 1 d . . .
C11 C 0.13550(14) 0.28518(16) 0.60723(8) 0.0523(3) Uani 1 1 d . . .
H11 H 0.2072 0.2803 0.5899 0.063 Uiso 1 1 calc R . .
C12 C 0.04406(15) 0.33947(17) 0.56066(8) 0.0588(4) Uani 1 1 d . . .
H12 H 0.0539 0.3696 0.5116 0.071 Uiso 1 1 calc R . .
C13 C -0.06127(14) 0.34882(16) 0.58679(8) 0.0565(4) Uani 1 1 d . . .
H13 H -0.1226 0.3850 0.5552 0.068 Uiso 1 1 calc R . .
C14 C -0.07712(11) 0.30469(14) 0.65997(7) 0.0446(3) Uani 1 1 d . . .
H14 H -0.1484 0.3135 0.6776 0.054 Uiso 1 1 calc R . .
C15 C 0.01343(10) 0.24724(11) 0.70707(6) 0.0353(2) Uani 1 1 d . . .
C16 C 0.00398(9) 0.18969(11) 0.78643(6) 0.0331(2) Uani 1 1 d . . .
H16 H -0.0020 0.0885 0.7840 0.040 Uiso 1 1 calc R . .
C17 C -0.09439(10) 0.24852(12) 0.82518(6) 0.0366(2) Uani 1 1 d . . .
C18 C -0.25303(13) 0.09367(19) 0.76415(10) 0.0644(4) Uani 1 1 d . . .
H18A H -0.2516 0.1198 0.7116 0.097 Uiso 1 1 calc R . .
H18B H -0.3299 0.0721 0.7732 0.097 Uiso 1 1 calc R . .
H18C H -0.2055 0.0139 0.7752 0.097 Uiso 1 1 calc R . .
C19 C 0.37501(10) 0.06858(14) 0.88213(7) 0.0435(3) Uani 1 1 d . . .
C20 C 0.35077(12) 0.00521(18) 0.94904(8) 0.0543(3) Uani 1 1 d . . .
H20 H 0.3149 0.0546 0.9850 0.065 Uiso 1 1 calc R . .
C21 C 0.38012(15) -0.13116(19) 0.96190(9) 0.0644(4) Uani 1 1 d . . .
H21 H 0.3636 -0.1733 1.0069 0.077 Uiso 1 1 calc R . .
C22 C 0.43397(14) -0.20788(18) 0.90935(10) 0.0614(4) Uani 1 1 d . . .
C23 C 0.45793(15) -0.14256(19) 0.84346(10) 0.0641(4) Uani 1 1 d . . .
H23 H 0.4941 -0.1919 0.8076 0.077 Uiso 1 1 calc R . .
C24 C 0.42945(12) -0.00538(18) 0.82930(8) 0.0559(3) Uani 1 1 d . . .
H24 H 0.4468 0.0370 0.7845 0.067 Uiso 1 1 calc R . .
C25 C 0.4657(2) -0.3574(2) 0.92454(14) 0.0932(7) Uani 1 1 d . . .
H25A H 0.4971 -0.3954 0.8810 0.140 Uiso 1 1 calc R . .
H25B H 0.3988 -0.4088 0.9338 0.140 Uiso 1 1 calc R . .
H25C H 0.5213 -0.3633 0.9686 0.140 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 O1 1.4286(11) . ?
S1 O2 1.4304(11) . ?
S1 N8 1.6339(10) . ?
S1 C19 1.7622(14) . ?
C1 C17 1.3946(17) . ?
C1 C2 1.399(2) . ?
C1 C18 1.501(2) . ?
C2 C3 1.379(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.3902(17) . ?
C4 H4 0.9300 . ?
C5 C17 1.3928(17) . ?
C5 C6 1.5003(18) . ?
C6 C7 1.5354(16) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N8 1.4791(14) . ?
C7 C16 1.5579(15) . ?
C7 H7 0.9800 . ?
N8 C9 1.4751(15) . ?
C9 C10 1.4977(17) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.3878(17) . ?
C10 C15 1.3953(17) . ?
C11 C12 1.383(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.373(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.3886(19) . ?
C13 H13 0.9300 . ?
C14 C15 1.3926(16) . ?
C14 H14 0.9300 . ?
C15 C16 1.5186(14) . ?
C16 C17 1.5181(15) . ?
C16 H16 0.9800 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.3844(18) . ?
C19 C24 1.3846(19) . ?
C20 C21 1.374(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.391(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.376(2) . ?
C22 C25 1.508(2) . ?
C23 C24 1.382(2) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
O1 S1 O2 119.90(8) . . ?
O1 S1 N8 106.70(6) . . ?
O2 S1 N8 106.59(7) . . ?
O1 S1 C19 108.31(7) . . ?
O2 S1 C19 107.01(7) . . ?
N8 S1 C19 107.82(6) . . ?
C17 C1 C2 116.71(14) . . ?
C17 C1 C18 122.44(12) . . ?
C2 C1 C18 120.84(13) . . ?
C3 C2 C1 121.89(14) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C4 C3 C2 120.91(13) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 118.48(14) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C4 C5 C17 120.60(12) . . ?
C4 C5 C6 128.50(12) . . ?
C17 C5 C6 110.90(10) . . ?
C5 C6 C7 102.32(10) . . ?
C5 C6 H6A 111.3 . . ?
C7 C6 H6A 111.3 . . ?
C5 C6 H6B 111.3 . . ?
C7 C6 H6B 111.3 . . ?
H6A C6 H6B 109.2 . . ?
N8 C7 C6 113.18(10) . . ?
N8 C7 C16 112.62(9) . . ?
C6 C7 C16 104.61(9) . . ?
N8 C7 H7 108.8 . . ?
C6 C7 H7 108.8 . . ?
C16 C7 H7 108.8 . . ?
C9 N8 C7 116.56(10) . . ?
C9 N8 S1 116.71(8) . . ?
C7 N8 S1 118.05(8) . . ?
N8 C9 C10 108.15(10) . . ?
N8 C9 H9A 110.1 . . ?
C10 C9 H9A 110.1 . . ?
N8 C9 H9B 110.1 . . ?
C10 C9 H9B 110.1 . . ?
H9A C9 H9B 108.4 . . ?
C11 C10 C15 120.62(12) . . ?
C11 C10 C9 122.12(12) . . ?
C15 C10 C9 117.26(10) . . ?
C12 C11 C10 119.85(13) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C13 C12 C11 120.01(12) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.60(13) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C15 120.14(12) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C10 118.75(11) . . ?
C14 C15 C16 124.37(11) . . ?
C10 C15 C16 116.86(10) . . ?
C17 C16 C15 114.39(9) . . ?
C17 C16 C7 101.10(9) . . ?
C15 C16 C7 111.89(9) . . ?
C17 C16 H16 109.7 . . ?
C15 C16 H16 109.7 . . ?
C7 C16 H16 109.7 . . ?
C5 C17 C1 121.35(11) . . ?
C5 C17 C16 109.99(10) . . ?
C1 C17 C16 128.66(11) . . ?
C1 C18 H18A 109.5 . . ?
C1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C24 119.84(13) . . ?
C20 C19 S1 120.24(11) . . ?
C24 C19 S1 119.92(10) . . ?
C21 C20 C19 119.47(15) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C20 C21 C22 121.72(15) . . ?
C20 C21 H21 119.1 . . ?
C22 C21 H21 119.1 . . ?
C23 C22 C21 117.83(15) . . ?
C23 C22 C25 121.24(19) . . ?
C21 C22 C25 120.93(18) . . ?
C22 C23 C24 121.53(16) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 H23 119.2 . . ?
C23 C24 C19 119.62(14) . . ?
C23 C24 H24 120.2 . . ?
C19 C24 H24 120.2 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        30.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.044
####################################################################### 
# 
# 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_3
_audit_block_doi                 10.5517/cc12gxct
_database_code_depnum_ccdc_archive 'CCDC 997436'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/ja504818p 2014
_audit_update_record             
;
2014-10-07 deposited with the CCDC.
2017-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 N O2'
_chemical_formula_weight         291.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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                   5.3653(12)
_cell_length_b                   15.987(3)
_cell_length_c                   8.8569(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.018(9)
_cell_angle_gamma                90.00
_cell_volume                     750.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    8454
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      22.85

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             308
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9737
_exptl_absorpt_correction_T_max  0.9933
_exptl_absorpt_process_details   'SADABS (Sheldrick, V2.10)'

_exptl_special_details           
; 
  'Blessing, Acta Cryst. (1995) A51, 33-38'  
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            33711
_diffrn_reflns_av_R_equivalents  0.0938
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         25.21
_reflns_number_total             1391
_reflns_number_gt                1177
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1447P)²+0.2391P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_chemical_absolute_configuration rm
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_number_reflns         1391
_refine_ls_number_parameters     200
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0943
_refine_ls_wR_factor_ref         0.2459
_refine_ls_wR_factor_gt          0.2378
_refine_ls_goodness_of_fit_ref   1.199
_refine_ls_restrained_S_all      1.198
_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
C1 C 0.8417(13) 0.1742(4) 0.5564(8) 0.0620(16) Uani 1 1 d . . .
H1 H 1.0124 0.1976 0.5769 0.074 Uiso 1 1 calc R . .
C2 C 0.6873(18) 0.2165(6) 0.4166(9) 0.084(2) Uani 1 1 d . . .
H2A H 0.5905 0.2631 0.4468 0.101 Uiso 1 1 calc R . .
H2B H 0.7957 0.2363 0.3462 0.101 Uiso 1 1 calc R . .
C3 C 0.5181(14) 0.1480(5) 0.3468(7) 0.0677(19) Uani 1 1 d . . .
C4 C 0.2926(19) 0.1543(7) 0.2387(9) 0.090(3) Uani 1 1 d . . .
H4 H 0.2277 0.2063 0.2064 0.108 Uiso 1 1 calc R . .
C5 C 0.1735(19) 0.0831(9) 0.1836(8) 0.098(3) Uani 1 1 d . . .
H5 H 0.0229 0.0863 0.1157 0.118 Uiso 1 1 calc R . .
C6 C 0.2750(17) 0.0058(8) 0.2279(9) 0.093(3) Uani 1 1 d . . .
H6 H 0.1931 -0.0421 0.1862 0.111 Uiso 1 1 calc R . .
C7 C 0.4982(13) -0.0029(5) 0.3339(7) 0.0679(19) Uani 1 1 d . . .
C8 C 0.6128(13) 0.0701(4) 0.3946(6) 0.0587(16) Uani 1 1 d . . .
C9 C 0.8506(10) 0.0808(4) 0.5143(7) 0.0538(15) Uani 1 1 d . . .
H9 H 0.9980 0.0719 0.4635 0.065 Uiso 1 1 calc R . .
C10 C 0.8721(10) 0.0229(4) 0.6499(6) 0.0504(14) Uani 1 1 d . . .
C11 C 1.0421(15) -0.0433(5) 0.6700(9) 0.0703(19) Uani 1 1 d . . .
H11 H 1.1555 -0.0514 0.6021 0.084 Uiso 1 1 calc R . .
C12 C 1.0402(19) -0.0977(5) 0.7947(11) 0.089(3) Uani 1 1 d . . .
H12 H 1.1560 -0.1413 0.8107 0.107 Uiso 1 1 calc R . .
C13 C 0.870(2) -0.0870(6) 0.8918(9) 0.086(2) Uani 1 1 d . . .
H13 H 0.8627 -0.1259 0.9691 0.104 Uiso 1 1 calc R . .
C14 C 0.7101(16) -0.0196(5) 0.8773(7) 0.077(2) Uani 1 1 d . . .
H14 H 0.5997 -0.0119 0.9473 0.093 Uiso 1 1 calc R . .
C15 C 0.7118(12) 0.0375(4) 0.7583(6) 0.0563(15) Uani 1 1 d . . .
C16 C 0.5609(12) 0.1161(5) 0.7404(7) 0.0631(18) Uani 1 1 d . . .
H16 H 0.4061 0.1083 0.6668 0.076 Uiso 1 1 calc R . .
C17 C 0.5012(16) 0.1572(7) 0.8895(8) 0.091(3) Uani 1 1 d . . .
H17A H 0.3387 0.1851 0.8715 0.109 Uiso 1 1 calc R . .
H17B H 0.4992 0.1156 0.9690 0.109 Uiso 1 1 calc R . .
O18 O 0.7004(13) 0.2164(5) 0.9321(6) 0.103(2) Uani 1 1 d . . .
C19 C 0.8162(16) 0.2330(5) 0.8092(10) 0.076(2) Uani 1 1 d . . .
N20 N 0.7149(10) 0.1830(3) 0.6907(6) 0.0614(14) Uani 1 1 d . . .
C21 C 0.604(2) -0.0875(5) 0.3692(11) 0.098(3) Uani 1 1 d . . .
H21A H 0.7724 -0.0899 0.3450 0.147 Uiso 1 1 calc R . .
H21B H 0.5006 -0.1283 0.3095 0.147 Uiso 1 1 calc R . .
H21C H 0.6086 -0.0991 0.4759 0.147 Uiso 1 1 calc R . .
O22 O 0.9772(16) 0.2842(4) 0.8103(9) 0.113(2) 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
C1 N20 1.467(8) . ?
C1 C2 1.535(12) . ?
C1 C9 1.541(10) . ?
C1 H1 0.9800 . ?
C2 C3 1.493(13) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C8 1.386(10) . ?
C3 C4 1.424(12) . ?
C4 C5 1.358(14) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(15) . ?
C5 H5 0.9300 . ?
C6 C7 1.408(12) . ?
C6 H6 0.9300 . ?
C7 C8 1.388(10) . ?
C7 C21 1.481(13) . ?
C8 C9 1.535(9) . ?
C9 C10 1.506(8) . ?
C9 H9 0.9800 . ?
C10 C11 1.390(9) . ?
C10 C15 1.405(8) . ?
C11 C12 1.407(12) . ?
C11 H11 0.9300 . ?
C12 C13 1.358(13) . ?
C12 H12 0.9300 . ?
C13 C14 1.372(13) . ?
C13 H13 0.9300 . ?
C14 C15 1.396(10) . ?
C14 H14 0.9300 . ?
C15 C16 1.490(10) . ?
C16 N20 1.460(9) . ?
C16 C17 1.553(9) . ?
C16 H16 0.9800 . ?
C17 O18 1.433(13) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
O18 C19 1.362(11) . ?
C19 O22 1.189(11) . ?
C19 N20 1.363(10) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
N20 C1 C2 110.6(6) . . ?
N20 C1 C9 108.9(5) . . ?
C2 C1 C9 105.3(6) . . ?
N20 C1 H1 110.6 . . ?
C2 C1 H1 110.6 . . ?
C9 C1 H1 110.6 . . ?
C3 C2 C1 103.1(6) . . ?
C3 C2 H2A 111.1 . . ?
C1 C2 H2A 111.1 . . ?
C3 C2 H2B 111.1 . . ?
C1 C2 H2B 111.1 . . ?
H2A C2 H2B 109.1 . . ?
C8 C3 C4 120.1(8) . . ?
C8 C3 C2 111.3(6) . . ?
C4 C3 C2 128.6(8) . . ?
C5 C4 C3 119.0(8) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 120.3(8) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C7 122.3(9) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 H6 118.9 . . ?
C8 C7 C6 117.0(8) . . ?
C8 C7 C21 123.6(7) . . ?
C6 C7 C21 119.3(8) . . ?
C3 C8 C7 121.2(6) . . ?
C3 C8 C9 109.6(6) . . ?
C7 C8 C9 129.1(6) . . ?
C10 C9 C8 115.7(5) . . ?
C10 C9 C1 113.8(5) . . ?
C8 C9 C1 102.8(5) . . ?
C10 C9 H9 108.1 . . ?
C8 C9 H9 108.1 . . ?
C1 C9 H9 108.1 . . ?
C11 C10 C15 119.9(6) . . ?
C11 C10 C9 122.5(6) . . ?
C15 C10 C9 117.6(5) . . ?
C10 C11 C12 119.1(7) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C13 C12 C11 120.5(8) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 120.8(8) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C15 120.4(8) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C10 119.0(7) . . ?
C14 C15 C16 124.3(6) . . ?
C10 C15 C16 116.6(5) . . ?
N20 C16 C15 109.0(5) . . ?
N20 C16 C17 98.5(6) . . ?
C15 C16 C17 116.6(6) . . ?
N20 C16 H16 110.7 . . ?
C15 C16 H16 110.7 . . ?
C17 C16 H16 110.7 . . ?
O18 C17 C16 105.0(6) . . ?
O18 C17 H17A 110.7 . . ?
C16 C17 H17A 110.7 . . ?
O18 C17 H17B 110.7 . . ?
C16 C17 H17B 110.7 . . ?
H17A C17 H17B 108.8 . . ?
C19 O18 C17 109.5(6) . . ?
O22 C19 O18 123.4(8) . . ?
O22 C19 N20 127.7(9) . . ?
O18 C19 N20 108.9(8) . . ?
C19 N20 C16 111.9(6) . . ?
C19 N20 C1 120.1(6) . . ?
C16 N20 C1 122.1(5) . . ?
C7 C21 H21A 109.5 . . ?
C7 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C7 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.21
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.092
#===END 

####################################################################### 
# 
# 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_2
_audit_block_doi                 10.5517/cc12gxbs
_database_code_depnum_ccdc_archive 'CCDC 997435'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/ja504818p 2014
_audit_update_record             
;
2014-10-07 deposited with the CCDC.
2017-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H23 N O2 S'
_chemical_formula_weight         389.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   11.0053(15)
_cell_length_b                   10.9876(14)
_cell_length_c                   16.699(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.056(6)
_cell_angle_gamma                90.00
_cell_volume                     1930.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9430
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      29.83

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9528
_exptl_absorpt_correction_T_max  0.9634
_exptl_absorpt_process_details   'SADABS (Sheldrick, V2.10)'

_exptl_special_details           
; 
  'Blessing, Acta Cryst. (1995) A51, 33-38'  
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            106023
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         30.01
_reflns_number_total             5627
_reflns_number_gt                4879
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0499P)²+0.7342P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5627
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0984
_refine_ls_wR_factor_gt          0.0933
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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 0.40267(2) 0.84495(2) 0.370966(16) 0.01692(7) Uani 1 1 d . . .
O1 O 0.48902(7) 0.93815(7) 0.41343(5) 0.02406(17) Uani 1 1 d . . .
O2 O 0.42357(8) 0.78429(8) 0.29986(5) 0.02386(17) Uani 1 1 d . . .
N1 N 0.26216(8) 0.90998(8) 0.33646(5) 0.01641(17) Uani 1 1 d . . .
C1 C 0.21161(10) 0.97187(9) 0.39888(6) 0.01598(18) Uani 1 1 d . . .
H1 H 0.2828 0.9857 0.4512 0.019 Uiso 1 1 calc R . .
C2 C 0.10408(10) 0.89637(9) 0.42097(6) 0.01662(19) Uani 1 1 d . . .
H2 H 0.1229 0.8927 0.4833 0.020 Uiso 1 1 calc R . .
C3 C 0.08500(10) 0.76871(9) 0.38631(7) 0.01775(19) Uani 1 1 d . . .
C4 C 0.10487(10) 0.74495(9) 0.30871(6) 0.01771(19) Uani 1 1 d . . .
C5 C 0.16278(10) 0.84604(9) 0.27081(6) 0.0185(2) Uani 1 1 d . . .
H5A H 0.2005 0.8118 0.2287 0.022 Uiso 1 1 calc R . .
H5B H 0.0957 0.9045 0.2421 0.022 Uiso 1 1 calc R . .
C6 C 0.15296(10) 1.09748(9) 0.36369(7) 0.01785(19) Uani 1 1 d . . .
H6 H 0.1631 1.1091 0.3066 0.021 Uiso 1 1 calc R . .
C7 C 0.01356(10) 1.08470(10) 0.35553(7) 0.0186(2) Uani 1 1 d . . .
C8 C -0.01438(10) 0.97302(10) 0.38510(6) 0.01798(19) Uani 1 1 d . . .
C9 C -0.13943(11) 0.94175(11) 0.37902(7) 0.0236(2) Uani 1 1 d . . .
H9 H -0.1584 0.8648 0.3984 0.028 Uiso 1 1 calc R . .
C10 C -0.23623(11) 1.02448(12) 0.34428(8) 0.0280(2) Uani 1 1 d . . .
H10 H -0.3217 1.0044 0.3404 0.034 Uiso 1 1 calc R . .
C11 C -0.20817(11) 1.13682(12) 0.31508(8) 0.0279(3) Uani 1 1 d . . .
H11 H -0.2749 1.1927 0.2912 0.034 Uiso 1 1 calc R . .
C12 C -0.08379(11) 1.16774(11) 0.32055(7) 0.0239(2) Uani 1 1 d . . .
H12 H -0.0650 1.2444 0.3008 0.029 Uiso 1 1 calc R . .
C13 C 0.04262(11) 0.67513(10) 0.42778(7) 0.0230(2) Uani 1 1 d . . .
H13 H 0.0304 0.6899 0.4809 0.028 Uiso 1 1 calc R . .
C14 C 0.01805(12) 0.55990(11) 0.39164(8) 0.0268(2) Uani 1 1 d . . .
H14 H -0.0113 0.4967 0.4201 0.032 Uiso 1 1 calc R . .
C15 C 0.03641(11) 0.53741(10) 0.31415(8) 0.0261(2) Uani 1 1 d . . .
H15 H 0.0187 0.4591 0.2893 0.031 Uiso 1 1 calc R . .
C16 C 0.08071(10) 0.62950(10) 0.27304(7) 0.0221(2) Uani 1 1 d . . .
H16 H 0.0946 0.6137 0.2205 0.026 Uiso 1 1 calc R . .
C17 C 0.39592(9) 0.73389(9) 0.44548(6) 0.01705(19) Uani 1 1 d . . .
C18 C 0.41435(10) 0.76798(10) 0.52872(7) 0.0206(2) Uani 1 1 d . . .
H18 H 0.4388 0.8488 0.5466 0.025 Uiso 1 1 calc R . .
C19 C 0.39633(11) 0.68171(11) 0.58498(7) 0.0237(2) Uani 1 1 d . . .
H19 H 0.4084 0.7044 0.6417 0.028 Uiso 1 1 calc R . .
C20 C 0.36085(10) 0.56244(11) 0.56011(7) 0.0239(2) Uani 1 1 d . . .
C21 C 0.34650(10) 0.53016(10) 0.47694(7) 0.0233(2) Uani 1 1 d . . .
H21 H 0.3247 0.4487 0.4594 0.028 Uiso 1 1 calc R . .
C22 C 0.36336(10) 0.61445(10) 0.41959(7) 0.0199(2) Uani 1 1 d . . .
H22 H 0.3529 0.5912 0.3632 0.024 Uiso 1 1 calc R . .
C23 C 0.21569(12) 1.20438(10) 0.41898(8) 0.0269(2) Uani 1 1 d . . .
H23A H 0.2075 1.1933 0.4754 0.040 Uiso 1 1 calc R . .
H23B H 0.1739 1.2803 0.3950 0.040 Uiso 1 1 calc R . .
H23C H 0.3059 1.2080 0.4220 0.040 Uiso 1 1 calc R . .
C24 C 0.33934(14) 0.47078(14) 0.62165(9) 0.0362(3) Uani 1 1 d . . .
H24A H 0.3295 0.5132 0.6710 0.054 Uiso 1 1 calc R . .
H24B H 0.4123 0.4156 0.6388 0.054 Uiso 1 1 calc R . .
H24C H 0.2622 0.4239 0.5953 0.054 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 O1 1.4350(8) . ?
S1 O2 1.4377(8) . ?
S1 N1 1.6466(9) . ?
S1 C17 1.7598(11) . ?
N1 C5 1.4793(13) . ?
N1 C1 1.4828(13) . ?
C1 C6 1.5634(14) . ?
C1 C2 1.5751(14) . ?
C1 H1 1.0000 . ?
C2 C3 1.5084(14) . ?
C2 C8 1.5196(14) . ?
C2 H2 1.0000 . ?
C3 C13 1.3942(15) . ?
C3 C4 1.4005(15) . ?
C4 C16 1.3934(15) . ?
C4 C5 1.5091(15) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.5064(15) . ?
C6 C23 1.5280(15) . ?
C6 H6 1.0000 . ?
C7 C8 1.3903(15) . ?
C7 C12 1.3980(15) . ?
C8 C9 1.3930(15) . ?
C9 C10 1.3911(17) . ?
C9 H9 0.9500 . ?
C10 C11 1.3947(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.3871(17) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.3945(16) . ?
C13 H13 0.9500 . ?
C14 C15 1.3892(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.3890(17) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C22 1.3953(15) . ?
C17 C18 1.3959(15) . ?
C18 C19 1.3892(16) . ?
C18 H18 0.9500 . ?
C19 C20 1.3954(17) . ?
C19 H19 0.9500 . ?
C20 C21 1.3968(17) . ?
C20 C24 1.5064(17) . ?
C21 C22 1.3833(16) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 119.72(5) . . ?
O1 S1 N1 106.32(5) . . ?
O2 S1 N1 105.87(5) . . ?
O1 S1 C17 107.74(5) . . ?
O2 S1 C17 108.22(5) . . ?
N1 S1 C17 108.56(5) . . ?
C5 N1 C1 112.99(8) . . ?
C5 N1 S1 117.88(7) . . ?
C1 N1 S1 117.42(7) . . ?
N1 C1 C6 109.83(8) . . ?
N1 C1 C2 112.68(8) . . ?
C6 C1 C2 107.29(8) . . ?
N1 C1 H1 109.0 . . ?
C6 C1 H1 109.0 . . ?
C2 C1 H1 109.0 . . ?
C3 C2 C8 110.94(8) . . ?
C3 C2 C1 115.44(8) . . ?
C8 C2 C1 103.44(8) . . ?
C3 C2 H2 108.9 . . ?
C8 C2 H2 108.9 . . ?
C1 C2 H2 108.9 . . ?
C13 C3 C4 119.20(10) . . ?
C13 C3 C2 121.63(10) . . ?
C4 C3 C2 119.11(9) . . ?
C16 C4 C3 120.22(10) . . ?
C16 C4 C5 122.81(10) . . ?
C3 C4 C5 116.79(9) . . ?
N1 C5 C4 110.49(8) . . ?
N1 C5 H5A 109.6 . . ?
C4 C5 H5A 109.6 . . ?
N1 C5 H5B 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C7 C6 C23 113.20(9) . . ?
C7 C6 C1 104.42(8) . . ?
C23 C6 C1 112.82(9) . . ?
C7 C6 H6 108.7 . . ?
C23 C6 H6 108.7 . . ?
C1 C6 H6 108.7 . . ?
C8 C7 C12 120.15(10) . . ?
C8 C7 C6 112.06(9) . . ?
C12 C7 C6 127.75(10) . . ?
C7 C8 C9 120.56(10) . . ?
C7 C8 C2 112.06(9) . . ?
C9 C8 C2 127.37(10) . . ?
C10 C9 C8 119.25(11) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C9 C10 C11 120.20(11) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 120.61(11) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 119.21(11) . . ?
C11 C12 H12 120.4 . . ?
C7 C12 H12 120.4 . . ?
C3 C13 C14 120.35(11) . . ?
C3 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 120.13(11) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 119.92(11) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C4 120.17(11) . . ?
C15 C16 H16 119.9 . . ?
C4 C16 H16 119.9 . . ?
C22 C17 C18 120.67(10) . . ?
C22 C17 S1 119.56(8) . . ?
C18 C17 S1 119.61(8) . . ?
C19 C18 C17 118.85(10) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
C18 C19 C20 121.50(10) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
C19 C20 C21 118.33(10) . . ?
C19 C20 C24 120.73(12) . . ?
C21 C20 C24 120.93(12) . . ?
C22 C21 C20 121.29(11) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C21 C22 C17 119.32(10) . . ?
C21 C22 H22 120.3 . . ?
C17 C22 H22 120.3 . . ?
C6 C23 H23A 109.5 . . ?
C6 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C6 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        30.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.049
