# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_160418_wk_sc
_database_code_depnum_ccdc_archive 'CCDC 1832181'
_audit_update_record             
;
2018-03-24 deposited with the CCDC.
2018-07-05 downloaded from the CCDC.
;
_audit_creation_date             2016-04-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H25 N O3 S'
_chemical_formula_sum            'C18 H25 N O3 S'
_chemical_formula_weight         335.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 o10 n2 S1'
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                   11.6879(8)
_cell_length_b                   18.2014(11)
_cell_length_c                   8.4879(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.767(5)
_cell_angle_gamma                90.00
_cell_volume                     1761.03(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2793
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5193
_cell_measurement_theta_min      3.3201
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92709
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.23
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11200
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.33
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0482119000
_diffrn_orient_matrix_UB_12      0.0235669000
_diffrn_orient_matrix_UB_13      0.0300135000
_diffrn_orient_matrix_UB_21      0.0392399000
_diffrn_orient_matrix_UB_22      -0.0280095000
_diffrn_orient_matrix_UB_23      -0.0124990000
_diffrn_orient_matrix_UB_31      -0.0027912000
_diffrn_orient_matrix_UB_32      0.0133384000
_diffrn_orient_matrix_UB_33      -0.0792991000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2382
_reflns_number_total             3211
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0432
_refine_ls_restrained_S_all      1.037
_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)+(0.0542P)²+0.4792P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1221
_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:
 C5(H5), C6(H6), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C16(H16), C17(H17)
2.d X=CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.e Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), 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 0.40683(5) 0.13764(3) 0.54370(6) 0.04526(19) Uani 1 d . . .
O1 O 0.30403(14) 0.01747(9) 0.92039(18) 0.0585(4) Uani 1 d . . .
O2 O 0.34440(14) 0.20227(8) 0.47897(17) 0.0574(4) Uani 1 d . . .
O3 O 0.44653(14) 0.08780(9) 0.43625(17) 0.0562(4) Uani 1 d . . .
N1 N 0.32432(15) 0.09141(9) 0.63818(19) 0.0435(4) Uani 1 d . . .
C1 C 0.2593(2) 0.12571(15) 1.0533(3) 0.0621(7) Uani 1 d . . .
H1A H 0.2851 0.1758 1.0783 0.075 Uiso 1 calc . . R
H1B H 0.2826 0.0969 1.1512 0.075 Uiso 1 calc . . R
C2 C 0.1269(2) 0.12467(17) 0.9997(3) 0.0712(8) Uani 1 d . . .
H2A H 0.0996 0.0743 0.9841 0.085 Uiso 1 calc . . R
H2B H 0.0926 0.1465 1.0827 0.085 Uiso 1 calc . . R
C3 C 0.0881(2) 0.16699(16) 0.8435(3) 0.0670(7) Uani 1 d . . .
H3A H 0.1129 0.2178 0.8602 0.080 Uiso 1 calc . . R
H3B H 0.0032 0.1661 0.8103 0.080 Uiso 1 calc . . R
C4 C 0.14086(19) 0.13334(13) 0.7113(3) 0.0524(6) Uani 1 d . . .
H4A H 0.1178 0.1623 0.6135 0.063 Uiso 1 calc . . R
H4B H 0.1104 0.0840 0.6882 0.063 Uiso 1 calc . . R
C5 C 0.27424(18) 0.13038(11) 0.7613(2) 0.0432(5) Uani 1 d . . .
H5 H 0.3030 0.1811 0.7669 0.052 Uiso 1 calc . . R
C6 C 0.3195(2) 0.09566(12) 0.9272(2) 0.0490(5) Uani 1 d . . .
H6 H 0.4036 0.1061 0.9615 0.059 Uiso 1 calc . . R
C7 C 0.3691(2) -0.01499(13) 0.8157(3) 0.0593(6) Uani 1 d . . .
H7A H 0.3630 -0.0680 0.8212 0.071 Uiso 1 calc . . R
H7B H 0.4512 -0.0019 0.8518 0.071 Uiso 1 calc . . R
C8 C 0.32567(19) 0.00973(11) 0.6418(3) 0.0482(5) Uani 1 d . . .
H8 H 0.3841 -0.0063 0.5822 0.058 Uiso 1 calc . . R
C9 C 0.2083(2) -0.02127(13) 0.5536(3) 0.0560(6) Uani 1 d . . .
C10 C 0.1501(3) -0.07091(15) 0.6180(4) 0.0816(9) Uani 1 d . . .
H10A H 0.0799 -0.0898 0.5582 0.098 Uiso 1 calc . . R
H10B H 0.1793 -0.0870 0.7232 0.098 Uiso 1 calc . . R
C11 C 0.1645(2) 0.00611(17) 0.3849(3) 0.0742(8) Uani 1 d . . .
H11A H 0.1478 0.0577 0.3873 0.111 Uiso 1 calc . . GR
H11B H 0.0943 -0.0199 0.3353 0.111 Uiso 1 calc . . GR
H11C H 0.2233 -0.0019 0.3237 0.111 Uiso 1 calc . . GR
C12 C 0.53065(18) 0.16685(12) 0.6906(2) 0.0441(5) Uani 1 d . . .
C13 C 0.5418(2) 0.23905(13) 0.7411(3) 0.0526(6) Uani 1 d . . .
H13 H 0.4845 0.2732 0.6970 0.063 Uiso 1 calc . . R
C14 C 0.6383(2) 0.26031(14) 0.8572(3) 0.0574(6) Uani 1 d . . .
H14 H 0.6453 0.3090 0.8911 0.069 Uiso 1 calc . . R
C15 C 0.72517(19) 0.21054(14) 0.9243(3) 0.0510(6) Uani 1 d . . .
C16 C 0.7121(2) 0.13818(13) 0.8722(3) 0.0553(6) Uani 1 d . . .
H16 H 0.7694 0.1039 0.9161 0.066 Uiso 1 calc . . R
C17 C 0.6157(2) 0.11593(13) 0.7566(3) 0.0528(6) Uani 1 d . . .
H17 H 0.6081 0.0671 0.7233 0.063 Uiso 1 calc . . R
C18 C 0.8313(2) 0.23507(16) 1.0491(3) 0.0700(7) Uani 1 d . . .
H18A H 0.8918 0.2504 0.9961 0.105 Uiso 1 calc . . GR
H18B H 0.8595 0.1950 1.1207 0.105 Uiso 1 calc . . GR
H18C H 0.8101 0.2754 1.1098 0.105 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 1.4286(15) . ?
S1 O3 1.4342(15) . ?
S1 N1 1.6195(17) . ?
S1 C12 1.770(2) . ?
O1 C6 1.434(3) . ?
O1 C7 1.420(3) . ?
N1 C5 1.486(2) . ?
N1 C8 1.487(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.514(4) . ?
C1 C6 1.507(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.514(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.523(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.523(3) . ?
C5 H5 0.9800 . ?
C5 C6 1.527(3) . ?
C6 H6 0.9800 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.519(3) . ?
C8 H8 0.9800 . ?
C8 C9 1.519(3) . ?
C9 C10 1.320(3) . ?
C9 C11 1.496(4) . ?
C10 H10A 0.9300 . ?
C10 H10B 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.380(3) . ?
C12 C17 1.384(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.379(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.386(3) . ?
C15 C16 1.387(3) . ?
C15 C18 1.509(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.381(3) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O3 119.06(9) . . ?
O2 S1 N1 107.99(9) . . ?
O2 S1 C12 106.99(10) . . ?
O3 S1 N1 107.34(9) . . ?
O3 S1 C12 107.98(10) . . ?
N1 S1 C12 106.91(9) . . ?
C7 O1 C6 110.99(17) . . ?
C5 N1 S1 118.07(13) . . ?
C5 N1 C8 117.83(16) . . ?
C8 N1 S1 121.65(14) . . ?
H1A C1 H1B 107.8 . . ?
C2 C1 H1A 109.0 . . ?
C2 C1 H1B 109.0 . . ?
C6 C1 H1A 109.0 . . ?
C6 C1 H1B 109.0 . . ?
C6 C1 C2 112.88(19) . . ?
C1 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 C1 110.2(2) . . ?
C3 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
C2 C3 H3A 109.6 . . ?
C2 C3 H3B 109.6 . . ?
C2 C3 C4 110.4(2) . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
C3 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
C3 C4 C5 111.43(18) . . ?
H4A C4 H4B 108.0 . . ?
C5 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
N1 C5 C4 111.04(16) . . ?
N1 C5 H5 107.4 . . ?
N1 C5 C6 109.94(17) . . ?
C4 C5 H5 107.4 . . ?
C4 C5 C6 113.31(18) . . ?
C6 C5 H5 107.4 . . ?
O1 C6 C1 108.33(18) . . ?
O1 C6 C5 111.01(17) . . ?
O1 C6 H6 108.3 . . ?
C1 C6 C5 112.56(19) . . ?
C1 C6 H6 108.3 . . ?
C5 C6 H6 108.3 . . ?
O1 C7 H7A 109.2 . . ?
O1 C7 H7B 109.2 . . ?
O1 C7 C8 112.01(18) . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
N1 C8 C7 108.41(17) . . ?
N1 C8 H8 107.0 . . ?
N1 C8 C9 110.92(18) . . ?
C7 C8 H8 107.0 . . ?
C9 C8 C7 116.1(2) . . ?
C9 C8 H8 107.0 . . ?
C10 C9 C8 122.8(2) . . ?
C10 C9 C11 121.8(2) . . ?
C11 C9 C8 115.4(2) . . ?
C9 C10 H10A 120.0 . . ?
C9 C10 H10B 120.0 . . ?
H10A C10 H10B 120.0 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 S1 120.75(17) . . ?
C13 C12 C17 120.1(2) . . ?
C17 C12 S1 119.11(17) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.7(2) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 119.3 . . ?
C13 C14 C15 121.3(2) . . ?
C15 C14 H14 119.3 . . ?
C14 C15 C16 118.1(2) . . ?
C14 C15 C18 120.6(2) . . ?
C16 C15 C18 121.3(2) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 C15 121.3(2) . . ?
C17 C16 H16 119.3 . . ?
C12 C17 H17 120.3 . . ?
C16 C17 C12 119.4(2) . . ?
C16 C17 H17 120.3 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C5 C4 115.88(17) . . . . ?
S1 N1 C5 C6 -117.92(17) . . . . ?
S1 N1 C8 C7 116.60(18) . . . . ?
S1 N1 C8 C9 -114.79(19) . . . . ?
S1 C12 C13 C14 179.14(16) . . . . ?
S1 C12 C17 C16 -179.44(16) . . . . ?
O1 C7 C8 N1 53.3(2) . . . . ?
O1 C7 C8 C9 -72.4(2) . . . . ?
O2 S1 N1 C5 -52.15(16) . . . . ?
O2 S1 N1 C8 146.01(15) . . . . ?
O2 S1 C12 C13 10.1(2) . . . . ?
O2 S1 C12 C17 -170.95(16) . . . . ?
O3 S1 N1 C5 178.32(14) . . . . ?
O3 S1 N1 C8 16.48(18) . . . . ?
O3 S1 C12 C13 139.39(17) . . . . ?
O3 S1 C12 C17 -41.67(19) . . . . ?
N1 S1 C12 C13 -105.39(18) . . . . ?
N1 S1 C12 C17 73.56(18) . . . . ?
N1 C5 C6 O1 -50.5(2) . . . . ?
N1 C5 C6 C1 -172.09(18) . . . . ?
N1 C8 C9 C10 -129.1(2) . . . . ?
N1 C8 C9 C11 53.2(3) . . . . ?
C1 C2 C3 C4 59.4(3) . . . . ?
C2 C1 C6 O1 -72.8(2) . . . . ?
C2 C1 C6 C5 50.3(3) . . . . ?
C2 C3 C4 C5 -56.7(3) . . . . ?
C3 C4 C5 N1 174.86(18) . . . . ?
C3 C4 C5 C6 50.6(3) . . . . ?
C4 C5 C6 O1 74.4(2) . . . . ?
C4 C5 C6 C1 -47.2(3) . . . . ?
C5 N1 C8 C7 -45.3(2) . . . . ?
C5 N1 C8 C9 83.3(2) . . . . ?
C6 O1 C7 C8 -64.2(2) . . . . ?
C6 C1 C2 C3 -56.7(3) . . . . ?
C7 O1 C6 C1 -173.93(17) . . . . ?
C7 O1 C6 C5 62.0(2) . . . . ?
C7 C8 C9 C10 -4.8(3) . . . . ?
C7 C8 C9 C11 177.5(2) . . . . ?
C8 N1 C5 C4 -81.6(2) . . . . ?
C8 N1 C5 C6 44.6(2) . . . . ?
C12 S1 N1 C5 62.67(16) . . . . ?
C12 S1 N1 C8 -99.17(17) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C13 C12 C17 C16 -0.5(3) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C13 C14 C15 C18 178.9(2) . . . . ?
C14 C15 C16 C17 0.2(3) . . . . ?
C15 C16 C17 C12 0.3(3) . . . . ?
C17 C12 C13 C14 0.2(3) . . . . ?
C18 C15 C16 C17 -179.2(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_180306_leu_noh_cw
_database_code_depnum_ccdc_archive 'CCDC 1832184'
_audit_update_record             
;
2018-03-24 deposited with the CCDC.
2018-07-05 downloaded from the CCDC.
;
_audit_creation_date             2018-03-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H25 N O4 S'
_chemical_formula_sum            'C18 H25 N O4 S'
_chemical_formula_weight         351.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S'
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'

_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.
;
_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_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2097(6)
_cell_length_b                   11.3718(10)
_cell_length_c                   11.4320(9)
_cell_angle_alpha                63.440(8)
_cell_angle_beta                 84.691(6)
_cell_angle_gamma                84.975(7)
_cell_volume                     949.27(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1949
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4119
_cell_measurement_theta_min      3.2754
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.928
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83674
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0813
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6022
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         3.282
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -72.00   15.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  -38.0000  -30.0000 87

#__ type_ start__ end____ width___ exp.time_
  2 omega  -38.00   64.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683   38.0000  150.0000 102

#__ type_ start__ end____ width___ exp.time_
  3 omega  -22.00   67.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   77.0000  -90.0000 89
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0815863000
_diffrn_orient_matrix_UB_12      0.0153936000
_diffrn_orient_matrix_UB_13      -0.0255422000
_diffrn_orient_matrix_UB_21      -0.0114265000
_diffrn_orient_matrix_UB_22      0.0601251000
_diffrn_orient_matrix_UB_23      0.0051099000
_diffrn_orient_matrix_UB_31      0.0276360000
_diffrn_orient_matrix_UB_32      -0.0320018000
_diffrn_orient_matrix_UB_33      0.0644194000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2133
_reflns_number_total             3462
_reflns_odcompleteness_completeness 99.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3462
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0524
_refine_ls_restrained_S_all      0.952
_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)+(0.0265P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.1075
_refine_special_details          ?
_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. Others
 Sof(C11A)=Sof(H11D)=Sof(H11E)=Sof(H11F)=1-FVAR(1)
 Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(H11C)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C6(H6)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B)
3.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C16(H16), C17(H17)
3.d X=CH2 refined with riding coordinates:
 C10(H10A,H10B)
3.e Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C18(H18A,H18B,H18C), C11(H11A,H11B,H11C),
 C11A(H11D,H11E,H11F)
;
_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 0.24305(8) 0.51516(6) 0.19149(6) 0.0509(2) Uani 1 1 d . . . . .
O1 O 0.6053(3) 0.35798(18) 0.50561(17) 0.0777(7) Uani 1 1 d . . . . .
O2 O 0.6188(2) 0.26023(16) 0.37669(16) 0.0627(5) Uani 1 1 d . . . . .
O3 O 0.2243(2) 0.63576(15) 0.20260(16) 0.0617(5) Uani 1 1 d . . . . .
O4 O 0.1901(2) 0.50792(17) 0.07903(16) 0.0656(6) Uani 1 1 d . . . . .
N1 N 0.4395(2) 0.47282(18) 0.19503(17) 0.0439(5) Uani 1 1 d . . . . .
C1 C 0.5388(3) 0.4955(2) 0.2843(2) 0.0442(6) Uani 1 1 d . . . . .
H1 H 0.469605 0.547617 0.320367 0.053 Uiso 1 1 calc R . . . .
C2 C 0.5898(3) 0.3679(3) 0.3980(2) 0.0532(7) Uani 1 1 d . . . . .
C3 C 0.6360(3) 0.2818(2) 0.2405(2) 0.0505(7) Uani 1 1 d . . . . .
H3 H 0.730823 0.334835 0.196480 0.061 Uiso 1 1 calc R . . . .
C4 C 0.4841(3) 0.3547(2) 0.1739(2) 0.0550(7) Uani 1 1 d . . . . .
H4A H 0.501261 0.380951 0.080600 0.066 Uiso 1 1 calc R . . . .
H4B H 0.394017 0.296254 0.206988 0.066 Uiso 1 1 calc R . . . .
C5 C 0.6885(3) 0.5750(2) 0.2113(2) 0.0554(7) Uani 1 1 d . . . . .
H5A H 0.757037 0.576972 0.274985 0.067 Uiso 1 1 calc R . . . .
H5B H 0.751760 0.529890 0.166020 0.067 Uiso 1 1 calc R . . . .
C6 C 0.6471(4) 0.7161(2) 0.1120(2) 0.0612(8) Uani 1 1 d . . . . .
H6 H 0.565797 0.713781 0.055583 0.073 Uiso 1 1 calc R . . . .
C7 C 0.8013(5) 0.7757(3) 0.0257(3) 0.1014(12) Uani 1 1 d . . . . .
H7A H 0.882984 0.778370 0.079174 0.152 Uiso 1 1 calc GR . . . .
H7B H 0.774308 0.863343 -0.038919 0.152 Uiso 1 1 calc GR . . . .
H7C H 0.842969 0.722498 -0.017280 0.152 Uiso 1 1 calc GR . . . .
C8 C 0.5753(4) 0.8012(3) 0.1762(3) 0.0856(10) Uani 1 1 d . . . . .
H8A H 0.477535 0.764034 0.228073 0.128 Uiso 1 1 calc GR . . . .
H8B H 0.549191 0.888284 0.109998 0.128 Uiso 1 1 calc GR . . . .
H8C H 0.653498 0.805550 0.231478 0.128 Uiso 1 1 calc GR . . . .
C9 C 0.6628(4) 0.1505(3) 0.2372(3) 0.0652(8) Uani 1 1 d . . . . .
C10 C 0.7603(4) 0.1421(3) 0.1406(3) 0.0875(11) Uani 1 1 d . . . . .
H10A H 0.791875 0.060122 0.143936 0.105 Uiso 1 1 calc R . . . .
H10B H 0.796645 0.218196 0.070076 0.105 Uiso 1 1 calc R . . . .
C12 C 0.1442(3) 0.3932(2) 0.3313(2) 0.0469(6) Uani 1 1 d . . . . .
C13 C 0.1398(3) 0.3991(3) 0.4502(2) 0.0575(7) Uani 1 1 d . . . . .
H13 H 0.190587 0.465669 0.456764 0.069 Uiso 1 1 calc R . . . .
C14 C 0.0590(4) 0.3048(3) 0.5589(3) 0.0649(8) Uani 1 1 d . . . . .
H14 H 0.054309 0.309690 0.638176 0.078 Uiso 1 1 calc R . . . .
C15 C -0.0146(3) 0.2038(3) 0.5522(3) 0.0611(8) Uani 1 1 d . . . . .
C16 C -0.0060(4) 0.1984(3) 0.4328(3) 0.0675(8) Uani 1 1 d . . . . .
H16 H -0.054313 0.130591 0.426640 0.081 Uiso 1 1 calc R . . . .
C17 C 0.0729(3) 0.2919(3) 0.3232(3) 0.0593(7) Uani 1 1 d . . . . .
H17 H 0.077984 0.286778 0.244037 0.071 Uiso 1 1 calc R . . . .
C18 C -0.1106(4) 0.1060(3) 0.6706(3) 0.0887(11) Uani 1 1 d . . . . .
H18A H -0.083970 0.111906 0.747718 0.133 Uiso 1 1 calc GR . . . .
H18B H -0.082877 0.018487 0.680100 0.133 Uiso 1 1 calc GR . . . .
H18C H -0.225794 0.125622 0.658846 0.133 Uiso 1 1 calc GR . . . .
C11 C 0.605(4) 0.0365(13) 0.3462(19) 0.143(9) Uani 0.69(4) 1 d . . P A 1
H11A H 0.640200 0.033599 0.425353 0.215 Uiso 0.69(4) 1 calc GR . P A 1
H11B H 0.648642 -0.040552 0.337537 0.215 Uiso 0.69(4) 1 calc GR . P A 1
H11C H 0.487712 0.039324 0.349588 0.215 Uiso 0.69(4) 1 calc GR . P A 1
C11A C 0.521(3) 0.054(3) 0.303(3) 0.088(7) Uani 0.31(4) 1 d . . P A 2
H11D H 0.477956 0.060062 0.381007 0.133 Uiso 0.31(4) 1 calc GR . P A 2
H11E H 0.561995 -0.034040 0.323974 0.133 Uiso 0.31(4) 1 calc GR . P A 2
H11F H 0.435453 0.078269 0.242805 0.133 Uiso 0.31(4) 1 calc GR . P A 2


_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 O3 1.4268(18) . ?
S1 O4 1.4327(17) . ?
S1 N1 1.641(2) . ?
S1 C12 1.764(2) . ?
O1 C2 1.201(3) . ?
O2 C2 1.350(3) . ?
O2 C3 1.459(3) . ?
N1 C1 1.483(3) . ?
N1 C4 1.478(3) . ?
C1 H1 0.9800 . ?
C1 C2 1.509(3) . ?
C1 C5 1.535(3) . ?
C3 H3 0.9800 . ?
C3 C4 1.501(3) . ?
C3 C9 1.507(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.525(3) . ?
C6 H6 0.9800 . ?
C6 C7 1.535(4) . ?
C6 C8 1.510(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.337(4) . ?
C9 C11 1.418(12) . ?
C9 C11A 1.56(2) . ?
C10 H10A 0.9300 . ?
C10 H10B 0.9300 . ?
C12 C13 1.387(3) . ?
C12 C17 1.379(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.383(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.378(4) . ?
C15 C16 1.389(4) . ?
C15 C18 1.516(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.378(4) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C11A H11D 0.9600 . ?
C11A H11E 0.9600 . ?
C11A H11F 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
O3 S1 O4 120.59(11) . . ?
O3 S1 N1 107.06(11) . . ?
O3 S1 C12 108.14(12) . . ?
O4 S1 N1 105.41(11) . . ?
O4 S1 C12 107.49(12) . . ?
N1 S1 C12 107.53(10) . . ?
C2 O2 C3 116.92(18) . . ?
C1 N1 S1 118.85(16) . . ?
C4 N1 S1 114.73(16) . . ?
C4 N1 C1 117.35(18) . . ?
N1 C1 H1 107.5 . . ?
N1 C1 C2 111.68(19) . . ?
N1 C1 C5 111.76(19) . . ?
C2 C1 H1 107.5 . . ?
C2 C1 C5 110.8(2) . . ?
C5 C1 H1 107.5 . . ?
O1 C2 O2 118.9(2) . . ?
O1 C2 C1 123.3(2) . . ?
O2 C2 C1 117.8(2) . . ?
O2 C3 H3 109.3 . . ?
O2 C3 C4 108.8(2) . . ?
O2 C3 C9 108.9(2) . . ?
C4 C3 H3 109.3 . . ?
C4 C3 C9 111.3(2) . . ?
C9 C3 H3 109.3 . . ?
N1 C4 C3 112.3(2) . . ?
N1 C4 H4A 109.1 . . ?
N1 C4 H4B 109.1 . . ?
C3 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.9 . . ?
C1 C5 H5A 108.7 . . ?
C1 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C6 C5 C1 114.4(2) . . ?
C6 C5 H5A 108.7 . . ?
C6 C5 H5B 108.7 . . ?
C5 C6 H6 108.1 . . ?
C5 C6 C7 109.5(3) . . ?
C7 C6 H6 108.1 . . ?
C8 C6 C5 112.6(2) . . ?
C8 C6 H6 108.1 . . ?
C8 C6 C7 110.4(2) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C3 C9 C11A 115.6(11) . . ?
C10 C9 C3 118.7(3) . . ?
C10 C9 C11 121.5(7) . . ?
C10 C9 C11A 119.8(12) . . ?
C11 C9 C3 119.1(6) . . ?
C9 C10 H10A 120.0 . . ?
C9 C10 H10B 120.0 . . ?
H10A C10 H10B 120.0 . . ?
C13 C12 S1 119.5(2) . . ?
C17 C12 S1 120.4(2) . . ?
C17 C12 C13 120.0(2) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 C12 119.3(3) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 H14 119.3 . . ?
C15 C14 C13 121.5(3) . . ?
C15 C14 H14 119.3 . . ?
C14 C15 C16 118.3(3) . . ?
C14 C15 C18 120.5(3) . . ?
C16 C15 C18 121.1(3) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.1(3) . . ?
C17 C16 H16 119.4 . . ?
C12 C17 H17 120.1 . . ?
C16 C17 C12 119.8(3) . . ?
C16 C17 H17 120.1 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C11A H11D 109.5 . . ?
C9 C11A H11E 109.5 . . ?
C9 C11A H11F 109.5 . . ?
H11D C11A H11E 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 109.5 . . ?

_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_b_a
_database_code_depnum_ccdc_archive 'CCDC 1836399'
_audit_update_record             
;
2018-04-11 deposited with the CCDC.
2018-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H15 N O4 S'
_chemical_formula_sum            'C13 H15 N O4 S'
_chemical_formula_weight         281.32

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 21'
_space_group_name_Hall           'P 2yb'

_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.
;

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

_cell_length_a                   10.8106(10)
_cell_length_b                   5.4540(5)
_cell_length_c                   11.7245(10)
_cell_angle_alpha                90
_cell_angle_beta                 104.012(5)
_cell_angle_gamma                90
_cell_volume                     670.72(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    4924
_cell_measurement_theta_min      3.89
_cell_measurement_theta_max      67.58

_exptl_crystal_description       blcok
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_F_000             296
_exptl_transmission_factor_min   0.6146
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    2.248
_shelx_estimated_absorpt_T_min   0.688
_shelx_estimated_absorpt_T_max   0.774
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9166
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_av_R_equivalents  0.0740
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.886
_diffrn_reflns_theta_max         68.403
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measured_fraction_theta_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_point_group_measured_fraction_full 0.950
_reflns_number_total             2305
_reflns_number_gt                1882
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_max     0.942
_reflns_Friedel_fraction_full    0.944

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0790P)²+0.2079P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.20(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2305
_refine_ls_number_parameters     174
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1550
_refine_ls_wR_factor_gt          0.1414
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.003
_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_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 0.43161(13) 0.7388(3) 0.69824(12) 0.0489(4) Uani 1 1 d . . . . .
C1 C 0.5568(6) 0.5532(12) 0.7743(5) 0.0469(14) Uani 1 1 d . . . . .
N1 N 0.3066(5) 0.5646(10) 0.6585(4) 0.0464(12) Uani 1 1 d . . . . .
O1 O 0.4604(4) 0.8218(8) 0.5920(4) 0.0555(11) Uani 1 1 d . . . . .
O2 O 0.4018(5) 0.9113(9) 0.7789(4) 0.0633(12) Uani 1 1 d . . . . .
C2 C 0.6147(6) 0.3943(14) 0.7134(5) 0.0535(16) Uani 1 1 d . . . . .
H2 H 0.5889 0.3878 0.6309 0.064 Uiso 1 1 calc R U . . .
O4 O 0.1103(5) 0.1802(11) 0.7942(4) 0.0780(17) Uani 1 1 d . . . . .
C4 C 0.7541(5) 0.2520(17) 0.8943(5) 0.0556(15) Uani 1 1 d . . . . .
O3 O 0.1161(4) 0.2006(13) 0.6098(4) 0.0735(16) Uani 1 1 d . . . . .
C3 C 0.7113(5) 0.2431(19) 0.7735(5) 0.0607(16) Uani 1 1 d . . . . .
H3 H 0.7488 0.1312 0.7310 0.073 Uiso 1 1 calc R U . . .
C8 C 0.3004(6) 0.3933(14) 0.5627(5) 0.0554(17) Uani 1 1 d . . . . .
H8A H 0.3519 0.2478 0.5910 0.066 Uiso 1 1 calc R U . . .
H8B H 0.3337 0.4700 0.5007 0.066 Uiso 1 1 calc R U . . .
C7 C 0.8609(7) 0.093(2) 0.9577(7) 0.079(3) Uani 1 1 d . . . . .
H7A H 0.8270 -0.0405 0.9958 0.119 Uiso 1 1 calc R U . . .
H7B H 0.9196 0.1890 1.0164 0.119 Uiso 1 1 calc R U . . .
H7C H 0.9054 0.0262 0.9020 0.119 Uiso 1 1 calc R U . . .
C6 C 0.5961(7) 0.5627(15) 0.8956(5) 0.0625(19) Uani 1 1 d . . . . .
H6 H 0.5554 0.6688 0.9381 0.075 Uiso 1 1 calc R U . . .
C5 C 0.6942(7) 0.4177(17) 0.9533(6) 0.0652(19) Uani 1 1 d . . . . .
H5 H 0.7221 0.4303 1.0355 0.078 Uiso 1 1 calc R U . . .
C9 C 0.1635(6) 0.3219(15) 0.5154(6) 0.0596(17) Uani 1 1 d . . . . .
H9 H 0.1121 0.4705 0.4886 0.072 Uiso 1 1 calc R U . . .
C10 C 0.1425(7) 0.1422(17) 0.4194(6) 0.069(2) Uani 1 1 d . . . . .
H10 H 0.1769 -0.0158 0.4361 0.082 Uiso 1 1 calc R U . . .
C11 C 0.0784(6) 0.1894(18) 0.3117(6) 0.072(2) Uani 1 1 d . . . . .
H11A H 0.0429 0.3457 0.2924 0.086 Uiso 1 1 calc R U . . .
H11B H 0.0680 0.0669 0.2537 0.086 Uiso 1 1 calc R U . . .
C12 C 0.1575(6) 0.2675(17) 0.7218(6) 0.0626(19) Uani 1 1 d . . . . .
C13 C 0.2608(6) 0.4567(14) 0.7559(6) 0.0564(17) Uani 1 1 d . . . . .
H13A H 0.2293 0.5895 0.7976 0.068 Uiso 1 1 calc R U . . .
H13B H 0.3336 0.3815 0.8113 0.068 Uiso 1 1 calc R U . . .


_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 1.425(4) . ?
S1 O1 1.429(4) . ?
S1 N1 1.625(5) . ?
S1 C1 1.751(7) . ?
C1 C2 1.367(9) . ?
C1 C6 1.383(8) . ?
N1 C8 1.450(8) . ?
N1 C13 1.473(7) . ?
C2 C3 1.382(10) . ?
C2 H2 0.9400 . ?
O4 C12 1.190(8) . ?
C4 C3 1.380(8) . ?
C4 C5 1.390(11) . ?
C4 C7 1.491(11) . ?
O3 C12 1.331(8) . ?
O3 C9 1.484(8) . ?
C3 H3 0.9400 . ?
C8 C9 1.500(9) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 H7C 0.9700 . ?
C6 C5 1.363(11) . ?
C6 H6 0.9400 . ?
C5 H5 0.9400 . ?
C9 C10 1.468(10) . ?
C9 H9 0.9900 . ?
C10 C11 1.310(10) . ?
C10 H10 0.9400 . ?
C11 H11A 0.9400 . ?
C11 H11B 0.9400 . ?
C12 C13 1.503(10) . ?
C13 H13A 0.9800 . ?
C13 H13B 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
O2 S1 O1 120.1(3) . . ?
O2 S1 N1 105.7(3) . . ?
O1 S1 N1 106.0(3) . . ?
O2 S1 C1 108.3(3) . . ?
O1 S1 C1 108.8(3) . . ?
N1 S1 C1 107.1(3) . . ?
C2 C1 C6 119.7(7) . . ?
C2 C1 S1 119.7(5) . . ?
C6 C1 S1 120.6(5) . . ?
C8 N1 C13 112.5(5) . . ?
C8 N1 S1 118.6(4) . . ?
C13 N1 S1 115.0(4) . . ?
C1 C2 C3 119.8(6) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C3 C4 C5 116.9(7) . . ?
C3 C4 C7 121.2(7) . . ?
C5 C4 C7 121.9(6) . . ?
C12 O3 C9 121.3(6) . . ?
C4 C3 C2 121.8(7) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
N1 C8 C9 108.1(5) . . ?
N1 C8 H8A 110.1 . . ?
C9 C8 H8A 110.1 . . ?
N1 C8 H8B 110.1 . . ?
C9 C8 H8B 110.1 . . ?
H8A C8 H8B 108.4 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C6 C1 119.8(7) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C6 C5 C4 122.0(6) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C10 C9 O3 104.9(6) . . ?
C10 C9 C8 114.4(6) . . ?
O3 C9 C8 109.2(5) . . ?
C10 C9 H9 109.4 . . ?
O3 C9 H9 109.4 . . ?
C8 C9 H9 109.4 . . ?
C11 C10 C9 123.7(8) . . ?
C11 C10 H10 118.1 . . ?
C9 C10 H10 118.1 . . ?
C10 C11 H11A 120.0 . . ?
C10 C11 H11B 120.0 . . ?
H11A C11 H11B 120.0 . . ?
O4 C12 O3 119.6(7) . . ?
O4 C12 C13 120.3(6) . . ?
O3 C12 C13 120.1(6) . . ?
N1 C13 C12 115.8(5) . . ?
N1 C13 H13A 108.3 . . ?
C12 C13 H13A 108.3 . . ?
N1 C13 H13B 108.3 . . ?
C12 C13 H13B 108.3 . . ?
H13A C13 H13B 107.4 . . ?

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
O2 S1 C1 C2 -171.2(5) . . . . ?
O1 S1 C1 C2 -39.1(6) . . . . ?
N1 S1 C1 C2 75.2(5) . . . . ?
O2 S1 C1 C6 9.9(6) . . . . ?
O1 S1 C1 C6 142.1(6) . . . . ?
N1 S1 C1 C6 -103.7(6) . . . . ?
O2 S1 N1 C8 170.8(5) . . . . ?
O1 S1 N1 C8 42.3(5) . . . . ?
C1 S1 N1 C8 -73.8(5) . . . . ?
O2 S1 N1 C13 -51.9(5) . . . . ?
O1 S1 N1 C13 179.6(4) . . . . ?
C1 S1 N1 C13 63.5(5) . . . . ?
C6 C1 C2 C3 0.5(10) . . . . ?
S1 C1 C2 C3 -178.3(6) . . . . ?
C5 C4 C3 C2 1.0(12) . . . . ?
C7 C4 C3 C2 -178.2(7) . . . . ?
C1 C2 C3 C4 -1.8(12) . . . . ?
C13 N1 C8 C9 61.3(7) . . . . ?
S1 N1 C8 C9 -160.4(5) . . . . ?
C2 C1 C6 C5 1.5(11) . . . . ?
S1 C1 C6 C5 -179.7(6) . . . . ?
C1 C6 C5 C4 -2.3(12) . . . . ?
C3 C4 C5 C6 1.1(11) . . . . ?
C7 C4 C5 C6 -179.7(8) . . . . ?
C12 O3 C9 C10 156.7(7) . . . . ?
C12 O3 C9 C8 33.7(9) . . . . ?
N1 C8 C9 C10 -178.3(6) . . . . ?
N1 C8 C9 O3 -61.2(7) . . . . ?
O3 C9 C10 C11 125.5(7) . . . . ?
C8 C9 C10 C11 -115.0(8) . . . . ?
C9 O3 C12 O4 174.1(7) . . . . ?
C9 O3 C12 C13 -4.4(11) . . . . ?
C8 N1 C13 C12 -31.7(8) . . . . ?
S1 N1 C13 C12 -171.6(5) . . . . ?
O4 C12 C13 N1 -176.1(7) . . . . ?
O3 C12 C13 N1 2.4(10) . . . . ?

_refine_diff_density_max         0.376
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_160531_ph_noh_cw
_database_code_depnum_ccdc_archive 'CCDC 1832182'
_audit_update_record             
;
2018-03-24 deposited with the CCDC.
2018-07-05 downloaded from the CCDC.
;
_audit_creation_date             2016-05-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H21 N O4 S'
_chemical_formula_sum            'C20 H21 N O4 S'
_chemical_formula_weight         371.44
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8 s1'
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                   17.4085(10)
_cell_length_b                   6.2355(3)
_cell_length_c                   17.4828(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.565(6)
_cell_angle_gamma                90.00
_cell_volume                     1871.38(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2542
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5137
_cell_measurement_theta_min      3.2605
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94902
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11286
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.47
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0412561000
_diffrn_orient_matrix_UB_12      -0.0040793000
_diffrn_orient_matrix_UB_13      -0.0051323000
_diffrn_orient_matrix_UB_21      -0.0004493000
_diffrn_orient_matrix_UB_22      -0.0689700000
_diffrn_orient_matrix_UB_23      -0.0323208000
_diffrn_orient_matrix_UB_31      0.0022357000
_diffrn_orient_matrix_UB_32      -0.0903791000
_diffrn_orient_matrix_UB_33      0.0249268000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2519
_reflns_number_total             3415
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0462
_refine_ls_restrained_S_all      1.023
_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)+(0.0516P)²+0.6654P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1228
_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:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C18(H18), C19(H19)
2.d X=CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), 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 0.17257(3) 0.68070(9) 0.42474(3) 0.0512(2) Uani 1 d . . .
O1 O 0.35277(11) 0.0711(3) 0.48383(11) 0.0673(5) Uani 1 d . . .
O2 O 0.40426(10) 0.3639(3) 0.44654(10) 0.0591(5) Uani 1 d . . .
O3 O 0.13006(10) 0.5830(3) 0.47883(10) 0.0699(5) Uani 1 d . . .
O4 O 0.17853(10) 0.9089(3) 0.42035(10) 0.0680(5) Uani 1 d . . .
N1 N 0.26208(10) 0.5876(3) 0.44592(9) 0.0437(4) Uani 1 d . . .
C1 C 0.30854(14) 0.5847(4) 0.61181(13) 0.0554(6) Uani 1 d . . .
H1 H 0.3200 0.7042 0.5839 0.067 Uiso 1 calc . . R
C2 C 0.31926(18) 0.5911(5) 0.69232(15) 0.0711(8) Uani 1 d . . .
H2 H 0.3385 0.7148 0.7184 0.085 Uiso 1 calc . . R
C3 C 0.30156(18) 0.4158(5) 0.73354(15) 0.0756(8) Uani 1 d . . .
H3 H 0.3094 0.4207 0.7874 0.091 Uiso 1 calc . . R
C4 C 0.27247(18) 0.2340(5) 0.69562(16) 0.0741(8) Uani 1 d . . .
H4 H 0.2591 0.1167 0.7235 0.089 Uiso 1 calc . . R
C5 C 0.26299(15) 0.2256(4) 0.61565(14) 0.0595(6) Uani 1 d . . .
H5 H 0.2444 0.1007 0.5899 0.071 Uiso 1 calc . . R
C6 C 0.28087(12) 0.4004(3) 0.57357(12) 0.0436(5) Uani 1 d . . .
C7 C 0.27345(13) 0.3785(3) 0.48579(11) 0.0428(5) Uani 1 d . . .
H7 H 0.2280 0.2885 0.4673 0.051 Uiso 1 calc . . R
C8 C 0.34591(14) 0.2599(4) 0.47092(12) 0.0478(5) Uani 1 d . . .
C9 C 0.39812(13) 0.5917(3) 0.43051(12) 0.0449(5) Uani 1 d . . .
H9 H 0.4111 0.6712 0.4793 0.054 Uiso 1 calc . . R
C10 C 0.31602(12) 0.6442(4) 0.39354(11) 0.0439(5) Uani 1 d . . .
H10A H 0.3119 0.7962 0.3818 0.053 Uiso 1 calc . . R
H10B H 0.3027 0.5654 0.3453 0.053 Uiso 1 calc . . R
C11 C 0.45669(13) 0.6454(4) 0.37870(12) 0.0514(6) Uani 1 d . . .
C12 C 0.48793(18) 0.8514(5) 0.38352(17) 0.0798(9) Uani 1 d . . .
H12A H 0.5226 0.8919 0.3510 0.096 Uiso 1 calc . . R
H12B H 0.4741 0.9486 0.4192 0.096 Uiso 1 calc . . R
C13 C 0.4748(2) 0.4912(6) 0.32654(19) 0.0923(10) Uani 1 d . . .
H13A H 0.4900 0.3604 0.3539 0.139 Uiso 1 calc . . GR
H13B H 0.5169 0.5421 0.3023 0.139 Uiso 1 calc . . GR
H13C H 0.4300 0.4652 0.2876 0.139 Uiso 1 calc . . GR
C14 C 0.13519(13) 0.5900(4) 0.33051(13) 0.0483(6) Uani 1 d . . .
C15 C 0.10175(14) 0.3892(4) 0.31879(15) 0.0593(6) Uani 1 d . . .
H15 H 0.0977 0.3008 0.3608 0.071 Uiso 1 calc . . R
C16 C 0.07440(16) 0.3208(4) 0.24387(17) 0.0705(8) Uani 1 d . . .
H16 H 0.0518 0.1857 0.2361 0.085 Uiso 1 calc . . R
C17 C 0.07973(16) 0.4478(5) 0.18047(16) 0.0737(8) Uani 1 d . . .
C18 C 0.11279(16) 0.6474(5) 0.19311(16) 0.0728(8) Uani 1 d . . .
H18 H 0.1165 0.7353 0.1509 0.087 Uiso 1 calc . . R
C19 C 0.14070(14) 0.7206(4) 0.26747(15) 0.0595(6) Uani 1 d . . .
H19 H 0.1629 0.8562 0.2750 0.071 Uiso 1 calc . . R
C20 C 0.0500(2) 0.3704(7) 0.09849(19) 0.1199(14) Uani 1 d . . .
H20A H -0.0027 0.4178 0.0827 0.180 Uiso 1 calc . . GR
H20B H 0.0517 0.2165 0.0971 0.180 Uiso 1 calc . . GR
H20C H 0.0822 0.4278 0.0639 0.180 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 O3 1.4303(18) . ?
S1 O4 1.4296(17) . ?
S1 N1 1.6464(18) . ?
S1 C14 1.761(2) . ?
O1 C8 1.201(3) . ?
O2 C8 1.333(3) . ?
O2 C9 1.448(3) . ?
N1 C7 1.476(3) . ?
N1 C10 1.460(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.389(3) . ?
C1 C6 1.375(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.372(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.367(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.379(3) . ?
C6 C7 1.525(3) . ?
C7 H7 0.9800 . ?
C7 C8 1.521(3) . ?
C9 H9 0.9800 . ?
C9 C10 1.504(3) . ?
C9 C11 1.510(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.392(3) . ?
C11 C13 1.397(4) . ?
C12 H12A 0.9300 . ?
C12 H12B 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.382(3) . ?
C14 C19 1.386(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.385(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.378(4) . ?
C17 C18 1.374(4) . ?
C17 C20 1.519(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.387(4) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 N1 105.98(10) . . ?
O3 S1 C14 109.30(11) . . ?
O4 S1 O3 120.63(11) . . ?
O4 S1 N1 106.79(10) . . ?
O4 S1 C14 106.75(10) . . ?
N1 S1 C14 106.62(10) . . ?
C8 O2 C9 120.21(17) . . ?
C7 N1 S1 117.74(14) . . ?
C10 N1 S1 117.19(13) . . ?
C10 N1 C7 117.39(17) . . ?
C2 C1 H1 120.2 . . ?
C6 C1 H1 120.2 . . ?
C6 C1 C2 119.6(2) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.6(3) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.7(2) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 119.5(2) . . ?
C1 C6 C7 121.9(2) . . ?
C5 C6 C7 118.5(2) . . ?
N1 C7 C6 112.23(16) . . ?
N1 C7 H7 108.2 . . ?
N1 C7 C8 113.49(18) . . ?
C6 C7 H7 108.2 . . ?
C8 C7 C6 106.35(17) . . ?
C8 C7 H7 108.2 . . ?
O1 C8 O2 118.7(2) . . ?
O1 C8 C7 120.2(2) . . ?
O2 C8 C7 121.04(19) . . ?
O2 C9 H9 109.2 . . ?
O2 C9 C10 109.34(18) . . ?
O2 C9 C11 107.35(18) . . ?
C10 C9 H9 109.2 . . ?
C10 C9 C11 112.48(17) . . ?
C11 C9 H9 109.2 . . ?
N1 C10 C9 110.02(16) . . ?
N1 C10 H10A 109.7 . . ?
N1 C10 H10B 109.7 . . ?
C9 C10 H10A 109.7 . . ?
C9 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
C12 C11 C9 117.7(2) . . ?
C12 C11 C13 123.1(3) . . ?
C13 C11 C9 119.2(2) . . ?
C11 C12 H12A 120.0 . . ?
C11 C12 H12B 120.0 . . ?
H12A C12 H12B 120.0 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 S1 120.71(18) . . ?
C15 C14 C19 119.8(2) . . ?
C19 C14 S1 119.45(18) . . ?
C14 C15 H15 120.4 . . ?
C14 C15 C16 119.3(2) . . ?
C16 C15 H15 120.4 . . ?
C15 C16 H16 119.1 . . ?
C17 C16 C15 121.7(3) . . ?
C17 C16 H16 119.1 . . ?
C16 C17 C20 121.2(3) . . ?
C18 C17 C16 118.3(2) . . ?
C18 C17 C20 120.5(3) . . ?
C17 C18 H18 119.3 . . ?
C17 C18 C19 121.4(3) . . ?
C19 C18 H18 119.3 . . ?
C14 C19 C18 119.5(2) . . ?
C14 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C7 C6 -85.62(19) . . . . ?
S1 N1 C7 C8 153.77(15) . . . . ?
S1 N1 C10 C9 166.79(14) . . . . ?
S1 C14 C15 C16 -178.6(2) . . . . ?
S1 C14 C19 C18 178.6(2) . . . . ?
O2 C9 C10 N1 60.4(2) . . . . ?
O2 C9 C11 C12 -151.0(2) . . . . ?
O2 C9 C11 C13 31.4(3) . . . . ?
O3 S1 N1 C7 24.69(17) . . . . ?
O3 S1 N1 C10 173.42(15) . . . . ?
O3 S1 C14 C15 -29.2(2) . . . . ?
O3 S1 C14 C19 151.91(19) . . . . ?
O4 S1 N1 C7 154.49(15) . . . . ?
O4 S1 N1 C10 -56.79(17) . . . . ?
O4 S1 C14 C15 -161.21(19) . . . . ?
O4 S1 C14 C19 19.9(2) . . . . ?
N1 S1 C14 C15 84.9(2) . . . . ?
N1 S1 C14 C19 -94.0(2) . . . . ?
N1 C7 C8 O1 -162.39(19) . . . . ?
N1 C7 C8 O2 20.4(3) . . . . ?
C1 C2 C3 C4 -0.7(5) . . . . ?
C1 C6 C7 N1 -27.1(3) . . . . ?
C1 C6 C7 C8 97.5(2) . . . . ?
C2 C1 C6 C5 1.0(4) . . . . ?
C2 C1 C6 C7 -175.5(2) . . . . ?
C2 C3 C4 C5 1.8(5) . . . . ?
C3 C4 C5 C6 -1.5(4) . . . . ?
C4 C5 C6 C1 0.1(4) . . . . ?
C4 C5 C6 C7 176.8(2) . . . . ?
C5 C6 C7 N1 156.3(2) . . . . ?
C5 C6 C7 C8 -79.0(3) . . . . ?
C6 C1 C2 C3 -0.8(4) . . . . ?
C6 C7 C8 O1 73.7(2) . . . . ?
C6 C7 C8 O2 -103.5(2) . . . . ?
C7 N1 C10 C9 -44.4(2) . . . . ?
C8 O2 C9 C10 -37.9(2) . . . . ?
C8 O2 C9 C11 -160.18(19) . . . . ?
C9 O2 C8 O1 -179.90(19) . . . . ?
C9 O2 C8 C7 -2.7(3) . . . . ?
C10 N1 C7 C6 125.72(19) . . . . ?
C10 N1 C7 C8 5.1(2) . . . . ?
C10 C9 C11 C12 88.7(3) . . . . ?
C10 C9 C11 C13 -88.9(3) . . . . ?
C11 C9 C10 N1 179.59(18) . . . . ?
C14 S1 N1 C7 -91.68(16) . . . . ?
C14 S1 N1 C10 57.05(17) . . . . ?
C14 C15 C16 C17 0.1(4) . . . . ?
C15 C14 C19 C18 -0.3(4) . . . . ?
C15 C16 C17 C18 -0.4(4) . . . . ?
C15 C16 C17 C20 179.6(3) . . . . ?
C16 C17 C18 C19 0.4(4) . . . . ?
C17 C18 C19 C14 0.0(4) . . . . ?
C19 C14 C15 C16 0.2(4) . . . . ?
C20 C17 C18 C19 -179.6(3) . . . . ?

####################################################################### 
# 
# 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_180327HG_WK1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1833770'
_audit_update_record             
;
2018-03-30 deposited with the CCDC.
2018-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H21 N O3 S'
_chemical_formula_sum            'C15 H21 N O3 S'
_chemical_formula_weight         295.39

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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

_cell_length_a                   9.1241(2)
_cell_length_b                   13.2825(2)
_cell_length_c                   25.2487(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.1180(10)
_cell_angle_gamma                90
_cell_volume                     3052.01(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9942
_cell_measurement_theta_min      3.51
_cell_measurement_theta_max      66.59

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    1.944
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29228
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.510
_diffrn_reflns_theta_max         66.587
_diffrn_reflns_theta_full        66.587
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5383
_reflns_number_gt                4672
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0462P)²+1.2592P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5383
_refine_ls_number_parameters     367
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0910
_refine_ls_wR_factor_gt          0.0863
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.009
_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_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 0.57058(4) 0.42788(3) 0.29190(2) 0.02721(11) Uani 1 1 d . . . . .
O1 O 0.60133(13) 0.52934(9) 0.27728(5) 0.0352(3) Uani 1 1 d . . . . .
N1 N 0.54920(14) 0.42735(10) 0.35679(5) 0.0243(3) Uani 1 1 d . . . . .
C1 C 0.39959(18) 0.39252(13) 0.26024(6) 0.0270(3) Uani 1 1 d . . . . .
S2 S -0.08551(4) 0.13990(3) 0.40581(2) 0.02574(11) Uani 1 1 d . . . . .
O2 O 0.67491(13) 0.35021(10) 0.28285(5) 0.0363(3) Uani 1 1 d . . . . .
N2 N -0.05347(14) 0.25984(10) 0.42087(5) 0.0247(3) Uani 1 1 d . . . . .
C2 C 0.29838(19) 0.46666(13) 0.24427(7) 0.0313(4) Uani 1 1 d . . . . .
H2 H 0.3233 0.5359 0.2480 0.038 Uiso 1 1 calc R U . . .
C3 C 0.1607(2) 0.43822(15) 0.22285(7) 0.0361(4) Uani 1 1 d . . . . .
H3 H 0.0917 0.4886 0.2113 0.043 Uiso 1 1 calc R U . . .
O4 O 0.41626(12) 0.38776(9) 0.45368(4) 0.0293(3) Uani 1 1 d . . . . .
C4 C 0.1215(2) 0.33731(15) 0.21798(7) 0.0352(4) Uani 1 1 d . . . . .
O5 O -0.17001(14) 0.13993(9) 0.35570(5) 0.0354(3) Uani 1 1 d . . . . .
C5 C 0.2267(2) 0.26456(14) 0.23268(7) 0.0351(4) Uani 1 1 d . . . . .
H5 H 0.2028 0.1953 0.2281 0.042 Uiso 1 1 calc R U . . .
O6 O -0.14570(12) 0.09368(9) 0.45049(5) 0.0309(3) Uani 1 1 d . . . . .
C6 C 0.36547(19) 0.29144(13) 0.25381(6) 0.0311(4) Uani 1 1 d . . . . .
H6 H 0.4363 0.2412 0.2638 0.037 Uiso 1 1 calc R U . . .
O7 O 0.07855(13) 0.45428(9) 0.42961(5) 0.0321(3) Uani 1 1 d . . . . .
C7 C -0.0317(2) 0.30783(19) 0.19714(9) 0.0533(6) Uani 1 1 d . . . . .
H7A H -0.0765 0.3633 0.1761 0.080 Uiso 1 1 calc R U . . .
H7B H -0.0912 0.2932 0.2270 0.080 Uiso 1 1 calc R U . . .
H7C H -0.0269 0.2479 0.1747 0.080 Uiso 1 1 calc R U . . .
C8 C 0.6178(2) 0.65036(14) 0.38293(8) 0.0367(4) Uani 1 1 d . . . . .
H8A H 0.6942 0.6067 0.3701 0.055 Uiso 1 1 calc R U . . .
H8B H 0.6278 0.6529 0.4218 0.055 Uiso 1 1 calc R U . . .
H8C H 0.6282 0.7183 0.3686 0.055 Uiso 1 1 calc R U . . .
C9 C 0.46907(19) 0.60919(13) 0.36490(7) 0.0293(4) Uani 1 1 d . . . . .
C10 C 0.43822(17) 0.49919(12) 0.37610(6) 0.0244(3) Uani 1 1 d . . . . .
H10 H 0.3389 0.4813 0.3595 0.029 Uiso 1 1 calc R U . . .
C11 C 0.4374(2) 0.48808(13) 0.43640(7) 0.0298(4) Uani 1 1 d . . . . .
H11A H 0.5320 0.5133 0.4530 0.036 Uiso 1 1 calc R U . . .
H11B H 0.3583 0.5309 0.4491 0.036 Uiso 1 1 calc R U . . .
C12 C 0.53274(17) 0.32520(13) 0.43780(6) 0.0273(3) Uani 1 1 d . . . . .
H12 H 0.6291 0.3526 0.4527 0.033 Uiso 1 1 calc R U . . .
C13 C 0.52953(18) 0.32384(12) 0.37781(6) 0.0268(3) Uani 1 1 d . . . . .
H13A H 0.6089 0.2797 0.3665 0.032 Uiso 1 1 calc R U . . .
H13B H 0.4345 0.2961 0.3631 0.032 Uiso 1 1 calc R U . . .
C14 C 0.5097(2) 0.22150(14) 0.46022(7) 0.0347(4) Uani 1 1 d . . . . .
H14A H 0.4157 0.1943 0.4453 0.052 Uiso 1 1 calc R U . . .
H14B H 0.5086 0.2257 0.4989 0.052 Uiso 1 1 calc R U . . .
H14C H 0.5897 0.1771 0.4510 0.052 Uiso 1 1 calc R U . . .
C15 C 0.3613(2) 0.66670(15) 0.34455(8) 0.0425(5) Uani 1 1 d . . . . .
H15A H 0.3761 0.7371 0.3408 0.051 Uiso 1 1 calc R U . . .
H15B H 0.2688 0.6377 0.3336 0.051 Uiso 1 1 calc R U . . .
C16 C 0.1579(2) 0.10007(13) 0.35140(7) 0.0328(4) Uani 1 1 d . . . . .
H16 H 0.1120 0.1390 0.3233 0.039 Uiso 1 1 calc R U . . .
C17 C 0.2960(2) 0.05934(14) 0.34684(7) 0.0362(4) Uani 1 1 d . . . . .
H17 H 0.3445 0.0706 0.3153 0.043 Uiso 1 1 calc R U . . .
C18 C 0.36548(19) 0.00217(13) 0.38747(7) 0.0338(4) Uani 1 1 d . . . . .
C19 C 0.2912(2) -0.01459(13) 0.43298(7) 0.0335(4) Uani 1 1 d . . . . .
H19 H 0.3363 -0.0542 0.4609 0.040 Uiso 1 1 calc R U . . .
C20 C 0.15278(19) 0.02534(12) 0.43834(7) 0.0294(4) Uani 1 1 d . . . . .
H20 H 0.1035 0.0131 0.4696 0.035 Uiso 1 1 calc R U . . .
C21 C 0.5179(2) -0.03959(17) 0.38297(9) 0.0496(5) Uani 1 1 d . . . . .
H21A H 0.5175 -0.0847 0.3522 0.074 Uiso 1 1 calc R U . . .
H21B H 0.5485 -0.0771 0.4153 0.074 Uiso 1 1 calc R U . . .
H21C H 0.5867 0.0159 0.3784 0.074 Uiso 1 1 calc R U . . .
C22 C -0.03055(18) 0.32457(12) 0.37410(6) 0.0281(4) Uani 1 1 d . . . . .
H22A H -0.1073 0.3102 0.3454 0.034 Uiso 1 1 calc R U . . .
H22B H 0.0664 0.3098 0.3606 0.034 Uiso 1 1 calc R U . . .
C23 C -0.03769(18) 0.43383(12) 0.38997(7) 0.0294(4) Uani 1 1 d . . . . .
H23 H -0.1343 0.4474 0.4049 0.035 Uiso 1 1 calc R U . . .
C24 C -0.0189(2) 0.50420(14) 0.34399(8) 0.0387(4) Uani 1 1 d . . . . .
H24A H 0.0742 0.4895 0.3285 0.058 Uiso 1 1 calc R U . . .
H24B H -0.0181 0.5740 0.3566 0.058 Uiso 1 1 calc R U . . .
H24C H -0.1004 0.4949 0.3170 0.058 Uiso 1 1 calc R U . . .
C25 C 0.0601(2) 0.39516(13) 0.47546(7) 0.0321(4) Uani 1 1 d . . . . .
H25A H -0.0333 0.4148 0.4903 0.039 Uiso 1 1 calc R U . . .
H25B H 0.1408 0.4110 0.5025 0.039 Uiso 1 1 calc R U . . .
C26 C 0.05806(17) 0.28135(12) 0.46590(6) 0.0258(3) Uani 1 1 d . . . . .
H26 H 0.1570 0.2596 0.4556 0.031 Uiso 1 1 calc R U . . .
C27 C 0.02807(19) 0.23213(12) 0.51811(6) 0.0284(4) Uani 1 1 d . . . . .
C28 C -0.1166(2) 0.25370(14) 0.54122(7) 0.0351(4) Uani 1 1 d . . . . .
H28A H -0.1968 0.2454 0.5136 0.053 Uiso 1 1 calc R U . . .
H28B H -0.1165 0.3229 0.5547 0.053 Uiso 1 1 calc R U . . .
H28C H -0.1304 0.2068 0.5704 0.053 Uiso 1 1 calc R U . . .
C29 C 0.08690(18) 0.08338(12) 0.39763(6) 0.0264(3) Uani 1 1 d . . . . .
C30 C 0.1327(2) 0.17908(14) 0.54413(8) 0.0377(4) Uani 1 1 d . . . . .
H30A H 0.1180 0.1533 0.5784 0.045 Uiso 1 1 calc R U . . .
H30B H 0.2227 0.1668 0.5285 0.045 Uiso 1 1 calc R U . . .


_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 1.4304(13) . ?
S1 O2 1.4332(13) . ?
S1 N1 1.6639(13) . ?
S1 C1 1.7648(17) . ?
N1 C13 1.489(2) . ?
N1 C10 1.498(2) . ?
C1 C6 1.385(2) . ?
C1 C2 1.390(2) . ?
S2 O6 1.4282(12) . ?
S2 O5 1.4337(12) . ?
S2 N2 1.6590(13) . ?
S2 C29 1.7685(17) . ?
N2 C22 1.488(2) . ?
N2 C26 1.498(2) . ?
C2 C3 1.384(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(3) . ?
C3 H3 0.9500 . ?
O4 C11 1.420(2) . ?
O4 C12 1.429(2) . ?
C4 C5 1.393(3) . ?
C4 C7 1.510(3) . ?
C5 C6 1.385(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
O7 C25 1.419(2) . ?
O7 C23 1.431(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.503(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C15 1.320(3) . ?
C9 C10 1.518(2) . ?
C10 C11 1.530(2) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C14 1.510(2) . ?
C12 C13 1.513(2) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9500 . ?
C15 H15B 0.9500 . ?
C16 C17 1.384(3) . ?
C16 C29 1.393(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.392(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.393(2) . ?
C18 C21 1.509(3) . ?
C19 C20 1.385(2) . ?
C19 H19 0.9500 . ?
C20 C29 1.387(2) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.508(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.510(2) . ?
C23 H23 1.0000 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.531(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.514(2) . ?
C26 H26 1.0000 . ?
C27 C30 1.323(2) . ?
C27 C28 1.508(2) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C30 H30A 0.9500 . ?
C30 H30B 0.9500 . ?

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 119.49(8) . . ?
O1 S1 N1 107.28(7) . . ?
O2 S1 N1 106.26(7) . . ?
O1 S1 C1 108.50(8) . . ?
O2 S1 C1 108.18(8) . . ?
N1 S1 C1 106.41(7) . . ?
C13 N1 C10 111.74(12) . . ?
C13 N1 S1 112.37(10) . . ?
C10 N1 S1 116.58(10) . . ?
C6 C1 C2 120.91(16) . . ?
C6 C1 S1 119.67(13) . . ?
C2 C1 S1 119.36(13) . . ?
O6 S2 O5 118.97(7) . . ?
O6 S2 N2 107.65(7) . . ?
O5 S2 N2 106.07(7) . . ?
O6 S2 C29 107.79(7) . . ?
O5 S2 C29 108.87(8) . . ?
N2 S2 C29 106.91(7) . . ?
C22 N2 C26 111.45(12) . . ?
C22 N2 S2 113.92(10) . . ?
C26 N2 S2 117.13(10) . . ?
C3 C2 C1 119.05(17) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 121.19(17) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C11 O4 C12 109.83(12) . . ?
C3 C4 C5 118.52(16) . . ?
C3 C4 C7 120.44(18) . . ?
C5 C4 C7 121.05(18) . . ?
C6 C5 C4 121.12(17) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C1 C6 C5 119.11(17) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C25 O7 C23 109.88(12) . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C15 C9 C8 122.59(17) . . ?
C15 C9 C10 119.11(16) . . ?
C8 C9 C10 117.98(15) . . ?
N1 C10 C9 114.43(13) . . ?
N1 C10 C11 108.30(13) . . ?
C9 C10 C11 106.99(13) . . ?
N1 C10 H10 109.0 . . ?
C9 C10 H10 109.0 . . ?
C11 C10 H10 109.0 . . ?
O4 C11 C10 114.01(13) . . ?
O4 C11 H11A 108.8 . . ?
C10 C11 H11A 108.8 . . ?
O4 C11 H11B 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.6 . . ?
O4 C12 C14 107.39(13) . . ?
O4 C12 C13 109.06(13) . . ?
C14 C12 C13 111.79(14) . . ?
O4 C12 H12 109.5 . . ?
C14 C12 H12 109.5 . . ?
C13 C12 H12 109.5 . . ?
N1 C13 C12 110.59(13) . . ?
N1 C13 H13A 109.5 . . ?
C12 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C9 C15 H15A 120.0 . . ?
C9 C15 H15B 120.0 . . ?
H15A C15 H15B 120.0 . . ?
C17 C16 C29 119.26(16) . . ?
C17 C16 H16 120.4 . . ?
C29 C16 H16 120.4 . . ?
C16 C17 C18 121.41(16) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C17 C18 C19 118.17(16) . . ?
C17 C18 C21 121.21(17) . . ?
C19 C18 C21 120.61(18) . . ?
C20 C19 C18 121.36(17) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C19 C20 C29 119.36(15) . . ?
C19 C20 H20 120.3 . . ?
C29 C20 H20 120.3 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N2 C22 C23 109.51(13) . . ?
N2 C22 H22A 109.8 . . ?
C23 C22 H22A 109.8 . . ?
N2 C22 H22B 109.8 . . ?
C23 C22 H22B 109.8 . . ?
H22A C22 H22B 108.2 . . ?
O7 C23 C22 108.94(13) . . ?
O7 C23 C24 107.50(13) . . ?
C22 C23 C24 112.46(15) . . ?
O7 C23 H23 109.3 . . ?
C22 C23 H23 109.3 . . ?
C24 C23 H23 109.3 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O7 C25 C26 114.76(14) . . ?
O7 C25 H25A 108.6 . . ?
C26 C25 H25A 108.6 . . ?
O7 C25 H25B 108.6 . . ?
C26 C25 H25B 108.6 . . ?
H25A C25 H25B 107.6 . . ?
N2 C26 C27 115.03(13) . . ?
N2 C26 C25 107.93(13) . . ?
C27 C26 C25 106.86(13) . . ?
N2 C26 H26 109.0 . . ?
C27 C26 H26 109.0 . . ?
C25 C26 H26 109.0 . . ?
C30 C27 C28 121.97(16) . . ?
C30 C27 C26 119.55(16) . . ?
C28 C27 C26 118.22(14) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C20 C29 C16 120.44(15) . . ?
C20 C29 S2 119.43(12) . . ?
C16 C29 S2 120.10(13) . . ?
C27 C30 H30A 120.0 . . ?
C27 C30 H30B 120.0 . . ?
H30A C30 H30B 120.0 . . ?

_refine_diff_density_max         0.257
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_180226_wk_0209
_database_code_depnum_ccdc_archive 'CCDC 1832183'
_audit_update_record             
;
2018-03-24 deposited with the CCDC.
2018-07-05 downloaded from the CCDC.
;
_audit_creation_date             2018-03-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H23 N O3 S'
_chemical_formula_sum            'C20 H23 N O3 S'
_chemical_formula_weight         357.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c h n o s'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   27.193(3)
_cell_length_b                   8.6013(7)
_cell_length_c                   16.5250(17)
_cell_angle_alpha                90
_cell_angle_beta                 101.302(11)
_cell_angle_gamma                90
_cell_volume                     3790.2(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2917
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3118
_cell_measurement_theta_min      3.1813
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.942
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67857
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12959
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         3.188
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -52.00   33.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808  -38.0000 -120.0000 85

#__ type_ start__ end____ width___ exp.time_
  2 omega   -1.00   36.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808  -89.0000  154.0000 37

#__ type_ start__ end____ width___ exp.time_
  3 omega   -7.00   85.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   38.0000 -180.0000 92

#__ type_ start__ end____ width___ exp.time_
  4 omega  -11.00   86.00   1.0000  110.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   38.0000   60.0000 97
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0204858000
_diffrn_orient_matrix_UB_12      -0.0454863000
_diffrn_orient_matrix_UB_13      -0.0204351000
_diffrn_orient_matrix_UB_21      -0.0127460000
_diffrn_orient_matrix_UB_22      0.0135127000
_diffrn_orient_matrix_UB_23      0.0329005000
_diffrn_orient_matrix_UB_31      -0.0112452000
_diffrn_orient_matrix_UB_32      0.0674251000
_diffrn_orient_matrix_UB_33      -0.0203410000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2089
_reflns_number_total             3471
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3471
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1006
_refine_ls_R_factor_gt           0.0554
_refine_ls_restrained_S_all      1.048
_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)+(0.0721P)²+1.6162P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1687
_refine_special_details          ?
_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), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C15(H15), C16(H16)
2.d X=CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.e Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.33114(3) 0.49689(8) 0.24637(4) 0.0660(3) Uani 1 1 d . . . . .
O1 O 0.39284(7) 0.1049(2) 0.38104(11) 0.0637(5) Uani 1 1 d . . . . .
O2 O 0.35909(9) 0.6384(2) 0.25897(13) 0.0816(7) Uani 1 1 d . . . . .
O3 O 0.30124(9) 0.4618(3) 0.16745(12) 0.0862(7) Uani 1 1 d . . . . .
N1 N 0.37118(9) 0.3561(2) 0.26872(13) 0.0597(6) Uani 1 1 d . . . . .
C1 C 0.42737(16) 0.3446(4) 0.5569(2) 0.0955(12) Uani 1 1 d . . . . .
H1 H 0.396116 0.389742 0.555294 0.115 Uiso 1 1 calc R . . . .
C2 C 0.4634(2) 0.3569(4) 0.6276(3) 0.1204(17) Uani 1 1 d . . . . .
H2 H 0.456374 0.410909 0.672775 0.144 Uiso 1 1 calc R . . . .
C3 C 0.50932(19) 0.2904(4) 0.6321(3) 0.1001(14) Uani 1 1 d . . . . .
H3 H 0.533650 0.298568 0.680017 0.120 Uiso 1 1 calc R . . . .
C4 C 0.51903(14) 0.2129(5) 0.5663(3) 0.1023(13) Uani 1 1 d . . . . .
H4 H 0.550269 0.167012 0.568812 0.123 Uiso 1 1 calc R . . . .
C5 C 0.48251(14) 0.2007(5) 0.4941(2) 0.0950(11) Uani 1 1 d . . . . .
H5 H 0.489679 0.146540 0.449149 0.114 Uiso 1 1 calc R . . . .
C6 C 0.43636(12) 0.2676(3) 0.48893(18) 0.0645(8) Uani 1 1 d . . . . .
C7 C 0.39720(11) 0.2605(3) 0.41130(17) 0.0596(7) Uani 1 1 d . . . . .
H7 H 0.364946 0.292322 0.423991 0.072 Uiso 1 1 calc R . . . .
C8 C 0.40945(11) 0.3663(3) 0.34497(17) 0.0637(8) Uani 1 1 d . . . . .
H8A H 0.411634 0.472676 0.364768 0.076 Uiso 1 1 calc R . . . .
H8B H 0.441841 0.337708 0.333199 0.076 Uiso 1 1 calc R . . . .
C9 C 0.35955(12) 0.1942(3) 0.23906(17) 0.0623(7) Uani 1 1 d . . . . .
H9 H 0.327197 0.197028 0.200530 0.075 Uiso 1 1 calc R . . . .
C10 C 0.35297(12) 0.0925(3) 0.31133(17) 0.0654(8) Uani 1 1 d . . . . .
H10A H 0.321834 0.120687 0.327879 0.078 Uiso 1 1 calc R . . . .
H10B H 0.350132 -0.014979 0.293298 0.078 Uiso 1 1 calc R . . . .
C11 C 0.29188(11) 0.4946(3) 0.31878(17) 0.0556(7) Uani 1 1 d . . . . .
C12 C 0.30360(12) 0.5814(3) 0.39059(19) 0.0665(8) Uani 1 1 d . . . . .
H12 H 0.330846 0.648860 0.398664 0.080 Uiso 1 1 calc R . . . .
C13 C 0.27489(12) 0.5673(4) 0.44964(19) 0.0717(8) Uani 1 1 d . . . . .
H13 H 0.283503 0.624689 0.498058 0.086 Uiso 1 1 calc R . . . .
C14 C 0.23359(12) 0.4709(3) 0.43968(19) 0.0648(8) Uani 1 1 d . . . . .
C15 C 0.22179(12) 0.3865(3) 0.3671(2) 0.0693(8) Uani 1 1 d . . . . .
H15 H 0.193959 0.321364 0.358738 0.083 Uiso 1 1 calc R . . . .
C16 C 0.25040(12) 0.3969(3) 0.30699(19) 0.0658(8) Uani 1 1 d . . . . .
H16 H 0.241954 0.338855 0.258796 0.079 Uiso 1 1 calc R . . . .
C17 C 0.20294(14) 0.4548(5) 0.5056(2) 0.0938(11) Uani 1 1 d . . . . .
H17A H 0.168484 0.437126 0.480382 0.141 Uiso 1 1 calc GR . . . .
H17B H 0.205575 0.548337 0.537803 0.141 Uiso 1 1 calc GR . . . .
H17C H 0.215186 0.368529 0.540670 0.141 Uiso 1 1 calc GR . . . .
C18 C 0.39811(13) 0.1423(4) 0.1912(2) 0.0784(9) Uani 1 1 d . . . . .
C19 C 0.4260(2) 0.0197(6) 0.2099(3) 0.146(2) Uani 1 1 d . . . . .
H19A H 0.447502 -0.011868 0.175727 0.176 Uiso 1 1 calc R . . . .
H19B H 0.424380 -0.036351 0.257418 0.176 Uiso 1 1 calc R . . . .
C20 C 0.39983(18) 0.2349(5) 0.1152(3) 0.1227(15) Uani 1 1 d . . . . .
H20A H 0.366315 0.260849 0.088076 0.184 Uiso 1 1 calc GR . . . .
H20B H 0.415674 0.174648 0.078647 0.184 Uiso 1 1 calc GR . . . .
H20C H 0.418607 0.328552 0.130191 0.184 Uiso 1 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 1.428(2) . ?
S1 O3 1.427(2) . ?
S1 N1 1.622(2) . ?
S1 C11 1.753(3) . ?
O1 C7 1.426(3) . ?
O1 C10 1.423(3) . ?
N1 C8 1.471(3) . ?
N1 C9 1.490(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.374(5) . ?
C1 C6 1.367(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.362(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.345(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.398(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.368(5) . ?
C6 C7 1.499(4) . ?
C7 H7 0.9800 . ?
C7 C8 1.511(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9 0.9800 . ?
C9 C10 1.519(4) . ?
C9 C18 1.500(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.385(4) . ?
C11 C16 1.389(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.369(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.380(4) . ?
C14 C15 1.384(4) . ?
C14 C17 1.502(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.380(4) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.300(5) . ?
C18 C20 1.495(5) . ?
C19 H19A 0.9300 . ?
C19 H19B 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 N1 106.78(13) . . ?
O2 S1 C11 106.73(13) . . ?
O3 S1 O2 120.33(13) . . ?
O3 S1 N1 106.68(12) . . ?
O3 S1 C11 107.89(14) . . ?
N1 S1 C11 107.92(12) . . ?
C10 O1 C7 110.59(19) . . ?
C8 N1 S1 118.78(18) . . ?
C8 N1 C9 114.0(2) . . ?
C9 N1 S1 122.24(19) . . ?
C2 C1 H1 119.2 . . ?
C6 C1 H1 119.2 . . ?
C6 C1 C2 121.6(4) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.5(4) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.2(4) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.5(4) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.8(4) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 117.5(3) . . ?
C1 C6 C7 120.8(3) . . ?
C5 C6 C7 121.7(3) . . ?
O1 C7 C6 109.6(2) . . ?
O1 C7 H7 108.7 . . ?
O1 C7 C8 109.0(2) . . ?
C6 C7 H7 108.7 . . ?
C6 C7 C8 112.0(2) . . ?
C8 C7 H7 108.7 . . ?
N1 C8 C7 111.5(2) . . ?
N1 C8 H8A 109.3 . . ?
N1 C8 H8B 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
N1 C9 H9 107.2 . . ?
N1 C9 C10 109.2(2) . . ?
N1 C9 C18 109.0(2) . . ?
C10 C9 H9 107.2 . . ?
C18 C9 H9 107.2 . . ?
C18 C9 C10 116.5(3) . . ?
O1 C10 C9 113.9(2) . . ?
O1 C10 H10A 108.8 . . ?
O1 C10 H10B 108.8 . . ?
C9 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C12 C11 S1 120.7(2) . . ?
C12 C11 C16 119.3(3) . . ?
C16 C11 S1 119.8(2) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.7(3) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 118.9 . . ?
C12 C13 C14 122.2(3) . . ?
C14 C13 H13 118.9 . . ?
C13 C14 C15 117.6(3) . . ?
C13 C14 C17 121.6(3) . . ?
C15 C14 C17 120.8(3) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 C14 121.5(3) . . ?
C16 C15 H15 119.3 . . ?
C11 C16 H16 120.2 . . ?
C15 C16 C11 119.7(3) . . ?
C15 C16 H16 120.2 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C9 123.5(3) . . ?
C19 C18 C20 121.2(4) . . ?
C20 C18 C9 115.1(3) . . ?
C18 C19 H19A 120.0 . . ?
C18 C19 H19B 120.0 . . ?
H19A C19 H19B 120.0 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
