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

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

data_p
_database_code_depnum_ccdc_archive 'CCDC 1481715'
_audit_update_record             
;
2016-05-24 deposited with the CCDC.
2016-10-27 downloaded from the CCDC.
;
_audit_creation_date             2016-01-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        Z2-52-2
_chemical_formula_moiety         'C20 H21 N O5 S'
_chemical_formula_sum            'C20 H21 N O5 S'
_chemical_formula_weight         387.44
_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 0.0033 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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.2335(18)
_cell_length_b                   10.875(3)
_cell_length_c                   14.080(4)
_cell_angle_alpha                69.0021(18)
_cell_angle_beta                 89.600(2)
_cell_angle_gamma                73.302(2)
_cell_volume                     984.7(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3824
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.067
_cell_measurement_theta_min      2.957
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  0.9846
_exptl_absorpt_correction_T_min  0.9622
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9275
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.05
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71000
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2612
_reflns_number_total             3449
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         1.465
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3449
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0991
_refine_ls_R_factor_gt           0.0792
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1530P)²+1.1513P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2246
_refine_ls_wR_factor_ref         0.2600
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C14(H14), C15(H15), C17(H17),
 C18(H18)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C8(H8A,H8B,H8C), C20(H20A,H20B,H20C)
;
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.74212(15) 0.51519(9) 0.18309(8) 0.0536(4) Uani 1 d . . .
O1 O 0.5584(5) 0.5922(3) 0.2004(3) 0.0747(9) Uani 1 d . . .
O2 O 0.8726(5) 0.5855(3) 0.1304(2) 0.0708(9) Uani 1 d . . .
O3 O 1.0128(4) 0.1203(3) 0.41560(19) 0.0528(7) Uani 1 d . . .
O4 O 1.8125(6) -0.1693(5) 0.3043(4) 0.1047(14) Uani 1 d . . .
O5 O 1.8074(7) -0.3223(5) 0.4517(5) 0.1249(17) Uani 1 d . . .
N1 N 0.8609(4) 0.4099(3) 0.2975(2) 0.0446(7) Uani 1 d . . .
C1 C 0.6613(15) 0.1093(7) -0.0013(5) 0.137(3) Uani 1 d . . .
H1A H 0.7518 0.0214 0.0391 0.205 Uiso 1 calc . . GR
H1B H 0.6908 0.1358 -0.0710 0.205 Uiso 1 calc . . GR
H1C H 0.5319 0.1024 0.0017 0.205 Uiso 1 calc . . GR
C2 C 0.6764(11) 0.2173(5) 0.0404(4) 0.0850(17) Uani 1 d . . .
C3 C 0.8302(9) 0.2709(5) 0.0220(4) 0.0778(14) Uani 1 d . . .
H3 H 0.9235 0.2424 -0.0178 0.093 Uiso 1 calc . . R
C4 C 0.8469(7) 0.3653(4) 0.0617(3) 0.0619(11) Uani 1 d . . .
H4 H 0.9506 0.4013 0.0487 0.074 Uiso 1 calc . . R
C5 C 0.7079(6) 0.4075(4) 0.1218(3) 0.0518(9) Uani 1 d . . .
C6 C 0.5549(7) 0.3554(5) 0.1397(3) 0.0674(12) Uani 1 d . . .
H6 H 0.4606 0.3839 0.1791 0.081 Uiso 1 calc . . R
C7 C 0.5417(9) 0.2606(6) 0.0992(4) 0.0889(18) Uani 1 d . . .
H7 H 0.4379 0.2247 0.1121 0.107 Uiso 1 calc . . R
C8 C 0.5833(7) 0.4177(5) 0.4080(4) 0.0714(13) Uani 1 d . . .
H8A H 0.6000 0.5011 0.4101 0.107 Uiso 1 calc . . GR
H8B H 0.5577 0.3628 0.4742 0.107 Uiso 1 calc . . GR
H8C H 0.4761 0.4406 0.3584 0.107 Uiso 1 calc . . GR
C9 C 0.7639(5) 0.3376(4) 0.3786(3) 0.0465(9) Uani 1 d . . .
C10 C 0.8486(5) 0.2052(4) 0.4332(3) 0.0492(9) Uani 1 d . . .
H10 H 0.7893 0.1654 0.4900 0.059 Uiso 1 calc . . R
C11 C 1.0605(5) 0.3271(4) 0.2974(3) 0.0453(8) Uani 1 d . . .
H11A H 1.1439 0.3288 0.3503 0.054 Uiso 1 calc . . R
H11B H 1.1066 0.3672 0.2320 0.054 Uiso 1 calc . . R
C12 C 1.0720(5) 0.1781(3) 0.3163(3) 0.0405(8) Uani 1 d . . .
H12 H 0.9808 0.1782 0.2651 0.049 Uiso 1 calc . . R
C13 C 1.2681(5) 0.0856(4) 0.3138(3) 0.0436(8) Uani 1 d . . .
C14 C 1.2869(6) -0.0063(4) 0.2651(3) 0.0590(11) Uani 1 d . . .
H14 H 1.1775 -0.0077 0.2317 0.071 Uiso 1 calc . . R
C15 C 1.4659(7) -0.0963(5) 0.2653(4) 0.0737(14) Uani 1 d . . .
H15 H 1.4774 -0.1588 0.2330 0.088 Uiso 1 calc . . R
C16 C 1.6260(6) -0.0922(5) 0.3137(4) 0.0703(13) Uani 1 d . . .
C17 C 1.6125(6) -0.0031(5) 0.3634(4) 0.0657(12) Uani 1 d . . .
H17 H 1.7229 -0.0020 0.3962 0.079 Uiso 1 calc . . R
C18 C 1.4337(6) 0.0846(4) 0.3642(3) 0.0550(10) Uani 1 d . . .
H18 H 1.4229 0.1443 0.3990 0.066 Uiso 1 calc . . R
C19 C 1.8775(12) -0.2787(8) 0.3741(6) 0.0946(19) Uani 1 d . . .
C20 C 2.0853(8) -0.3552(7) 0.3494(7) 0.116(3) Uani 1 d . . .
H20A H 2.0726 -0.3627 0.2841 0.174 Uiso 1 calc . . GR
H20B H 2.1356 -0.4460 0.4014 0.174 Uiso 1 calc . . GR
H20C H 2.1727 -0.3029 0.3480 0.174 Uiso 1 calc . . GR


_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 1.424(3) . ?
S1 O2 1.422(3) . ?
S1 N1 1.666(3) . ?
S1 C5 1.752(4) . ?
O3 C10 1.362(4) . ?
O3 C12 1.432(4) . ?
O4 C16 1.402(5) . ?
O4 C19 1.204(8) . ?
O5 C19 1.197(7) . ?
N1 C9 1.441(5) . ?
N1 C11 1.466(4) . ?
C1 C2 1.519(8) . ?
C2 C3 1.380(8) . ?
C2 C7 1.364(9) . ?
C3 C4 1.366(6) . ?
C4 C5 1.392(6) . ?
C5 C6 1.366(6) . ?
C6 C7 1.370(8) . ?
C8 C9 1.494(5) . ?
C9 C10 1.322(5) . ?
C11 C12 1.523(5) . ?
C12 C13 1.493(5) . ?
C13 C14 1.378(5) . ?
C13 C18 1.392(5) . ?
C14 C15 1.380(6) . ?
C15 C16 1.368(7) . ?
C16 C17 1.367(7) . ?
C17 C18 1.372(6) . ?
C19 C20 1.598(9) . ?

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 N1 107.02(17) . . ?
O1 S1 C5 109.4(2) . . ?
O2 S1 O1 119.8(2) . . ?
O2 S1 N1 105.40(18) . . ?
O2 S1 C5 108.50(19) . . ?
N1 S1 C5 105.86(16) . . ?
C10 O3 C12 113.3(3) . . ?
C19 O4 C16 114.4(6) . . ?
C9 N1 S1 121.4(2) . . ?
C9 N1 C11 112.5(3) . . ?
C11 N1 S1 115.9(2) . . ?
C3 C2 C1 120.5(6) . . ?
C7 C2 C1 120.9(6) . . ?
C7 C2 C3 118.6(5) . . ?
C4 C3 C2 120.6(5) . . ?
C3 C4 C5 119.7(4) . . ?
C4 C5 S1 119.6(3) . . ?
C6 C5 S1 120.4(3) . . ?
C6 C5 C4 119.8(4) . . ?
C5 C6 C7 119.4(5) . . ?
C2 C7 C6 121.9(5) . . ?
N1 C9 C8 119.2(3) . . ?
C10 C9 N1 119.1(3) . . ?
C10 C9 C8 121.2(4) . . ?
C9 C10 O3 127.3(3) . . ?
N1 C11 C12 111.0(3) . . ?
O3 C12 C11 107.8(3) . . ?
O3 C12 C13 107.3(3) . . ?
C13 C12 C11 115.6(3) . . ?
C14 C13 C12 120.0(3) . . ?
C14 C13 C18 118.5(3) . . ?
C18 C13 C12 121.5(3) . . ?
C13 C14 C15 120.9(4) . . ?
C16 C15 C14 119.0(4) . . ?
C15 C16 O4 120.4(4) . . ?
C17 C16 O4 117.6(4) . . ?
C17 C16 C15 121.7(4) . . ?
C16 C17 C18 119.0(4) . . ?
C17 C18 C13 121.0(4) . . ?
O4 C19 C20 108.0(6) . . ?
O5 C19 O4 127.4(7) . . ?
O5 C19 C20 124.5(7) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_p
_database_code_depnum_ccdc_archive 'CCDC 1481716'
_audit_update_record             
;
2016-05-24 deposited with the CCDC.
2016-10-27 downloaded from the CCDC.
;
_audit_creation_date             2016-01-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H21 N O3 S'
_chemical_formula_sum            'C18 H21 N O3 S'
_chemical_formula_weight         331.42
_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 0.0033 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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   13.490(4)
_cell_length_b                   7.784(3)
_cell_length_c                   16.677(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.231(3)
_cell_angle_gamma                90.00
_cell_volume                     1689.7(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1125
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      19.918
_cell_measurement_theta_min      3.049
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  0.9857
_exptl_absorpt_correction_T_min  0.9600
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_unetI/netI     0.0741
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7765
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.53
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71000
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1710
_reflns_number_total             2967
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2967
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1152
_refine_ls_R_factor_gt           0.0507
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0432P)²+0.2578P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.1166
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C18(H18A,H18B,H18C)
;
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.20792(6) 0.59744(11) 0.64468(5) 0.0466(3) Uani 1 d . . .
O1 O 0.42883(16) 1.0055(2) 0.66357(12) 0.0518(6) Uani 1 d . . .
O2 O 0.14446(15) 0.6151(3) 0.70048(13) 0.0601(6) Uani 1 d . . .
O3 O 0.24919(15) 0.4332(2) 0.63219(13) 0.0543(6) Uani 1 d . . .
N1 N 0.30453(17) 0.7238(3) 0.67733(15) 0.0461(7) Uani 1 d . . .
C1 C 0.5374(3) 0.7625(4) 0.52147(19) 0.0539(9) Uani 1 d . . .
H1 H 0.4776 0.7267 0.4832 0.065 Uiso 1 calc . . R
C2 C 0.6311(3) 0.7381(4) 0.5048(2) 0.0634(10) Uani 1 d . . .
H2 H 0.6345 0.6848 0.4557 0.076 Uiso 1 calc . . R
C3 C 0.7192(3) 0.7923(5) 0.5605(3) 0.0672(11) Uani 1 d . . .
H3 H 0.7825 0.7764 0.5492 0.081 Uiso 1 calc . . R
C4 C 0.7138(3) 0.8701(5) 0.6330(2) 0.0668(10) Uani 1 d . . .
H4 H 0.7736 0.9077 0.6707 0.080 Uiso 1 calc . . R
C5 C 0.6208(3) 0.8927(4) 0.6499(2) 0.0546(9) Uani 1 d . . .
H5 H 0.6179 0.9445 0.6995 0.066 Uiso 1 calc . . R
C6 C 0.5316(2) 0.8396(4) 0.59449(19) 0.0421(8) Uani 1 d . . .
C7 C 0.4286(2) 0.8594(4) 0.61180(18) 0.0454(8) Uani 1 d . . .
H7 H 0.3765 0.8763 0.5590 0.054 Uiso 1 calc . . R
C8 C 0.4010(2) 0.7015(4) 0.65423(19) 0.0458(8) Uani 1 d . . .
H8A H 0.3950 0.6037 0.6172 0.055 Uiso 1 calc . . R
H8B H 0.4557 0.6774 0.7037 0.055 Uiso 1 calc . . R
C9 C 0.2961(2) 0.8858(4) 0.72111(19) 0.0481(8) Uani 1 d . . .
H9 H 0.2237 0.9030 0.7196 0.058 Uiso 1 calc . . R
C10 C 0.3571(3) 0.8754(4) 0.81139(19) 0.0636(10) Uani 1 d . . .
H10A H 0.3313 0.7830 0.8382 0.095 Uiso 1 calc . . GR
H10B H 0.3506 0.9816 0.8388 0.095 Uiso 1 calc . . GR
H10C H 0.4282 0.8551 0.8143 0.095 Uiso 1 calc . . GR
C11 C 0.3291(3) 1.0320(4) 0.6748(2) 0.0576(9) Uani 1 d . . .
H11A H 0.2802 1.0442 0.6208 0.069 Uiso 1 calc . . R
H11B H 0.3286 1.1379 0.7053 0.069 Uiso 1 calc . . R
C12 C 0.1355(2) 0.6686(4) 0.54660(18) 0.0399(7) Uani 1 d . . .
C13 C 0.1739(3) 0.6539(5) 0.4786(2) 0.0660(10) Uani 1 d . . .
H13 H 0.2387 0.6069 0.4841 0.079 Uiso 1 calc . . R
C14 C 0.1162(3) 0.7089(5) 0.4019(2) 0.0700(11) Uani 1 d . . .
H14 H 0.1437 0.7008 0.3564 0.084 Uiso 1 calc . . R
C15 C 0.0193(2) 0.7751(4) 0.3908(2) 0.0542(9) Uani 1 d . . .
C16 C -0.0174(3) 0.7865(5) 0.4591(2) 0.0686(11) Uani 1 d . . .
H16 H -0.0830 0.8306 0.4532 0.082 Uiso 1 calc . . R
C17 C 0.0393(2) 0.7350(4) 0.5372(2) 0.0597(10) Uani 1 d . . .
H17 H 0.0122 0.7456 0.5829 0.072 Uiso 1 calc . . R
C18 C -0.0430(3) 0.8309(5) 0.3064(2) 0.0829(12) Uani 1 d . . .
H18A H -0.0401 0.9537 0.3022 0.124 Uiso 1 calc . . GR
H18B H -0.1131 0.7954 0.2986 0.124 Uiso 1 calc . . GR
H18C H -0.0157 0.7793 0.2645 0.124 Uiso 1 calc . . GR


_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 1.427(2) . ?
S1 O3 1.431(2) . ?
S1 N1 1.609(2) . ?
S1 C12 1.760(3) . ?
O1 C7 1.427(3) . ?
O1 C11 1.421(3) . ?
N1 C8 1.462(3) . ?
N1 C9 1.477(3) . ?
C1 C2 1.377(4) . ?
C1 C6 1.378(4) . ?
C2 C3 1.369(5) . ?
C3 C4 1.372(5) . ?
C4 C5 1.368(4) . ?
C5 C6 1.374(4) . ?
C6 C7 1.500(4) . ?
C7 C8 1.513(4) . ?
C9 C10 1.517(4) . ?
C9 C11 1.508(4) . ?
C12 C13 1.370(4) . ?
C12 C17 1.367(4) . ?
C13 C14 1.379(4) . ?
C14 C15 1.371(4) . ?
C15 C16 1.360(4) . ?
C15 C18 1.501(4) . ?
C16 C17 1.385(4) . ?

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 O3 120.25(13) . . ?
O2 S1 N1 106.97(13) . . ?
O2 S1 C12 107.11(14) . . ?
O3 S1 N1 106.48(13) . . ?
O3 S1 C12 106.74(13) . . ?
N1 S1 C12 108.95(13) . . ?
C11 O1 C7 110.1(2) . . ?
C8 N1 S1 122.45(19) . . ?
C8 N1 C9 114.9(2) . . ?
C9 N1 S1 121.89(19) . . ?
C2 C1 C6 120.4(3) . . ?
C3 C2 C1 120.0(3) . . ?
C2 C3 C4 119.8(3) . . ?
C5 C4 C3 120.2(3) . . ?
C4 C5 C6 120.7(3) . . ?
C1 C6 C7 119.0(3) . . ?
C5 C6 C1 118.9(3) . . ?
C5 C6 C7 122.1(3) . . ?
O1 C7 C6 110.1(2) . . ?
O1 C7 C8 109.0(2) . . ?
C6 C7 C8 111.1(2) . . ?
N1 C8 C7 111.8(2) . . ?
N1 C9 C10 110.7(2) . . ?
N1 C9 C11 108.7(2) . . ?
C11 C9 C10 113.1(3) . . ?
O1 C11 C9 112.0(2) . . ?
C13 C12 S1 120.3(2) . . ?
C17 C12 S1 120.2(2) . . ?
C17 C12 C13 119.4(3) . . ?
C12 C13 C14 119.9(3) . . ?
C15 C14 C13 121.9(3) . . ?
C14 C15 C18 121.0(3) . . ?
C16 C15 C14 117.1(3) . . ?
C16 C15 C18 121.9(3) . . ?
C15 C16 C17 122.5(3) . . ?
C12 C17 C16 119.3(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
