# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1859743'
_audit_update_record             
;
2018-08-01 deposited with the CCDC.
2018-09-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H25 N O3 S'
_chemical_formula_sum            'C18 H25 N O3 S'
_chemical_formula_weight         335.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.8259(6)
_cell_length_b                   9.5135(8)
_cell_length_c                   22.6470(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1686.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9894
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      29.5

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.320
_exptl_absorpt_coefficient_mu    0.207
_shelx_estimated_absorpt_T_min   0.902
_shelx_estimated_absorpt_T_max   0.937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
SADABS. G. M. Sheldrick. Apex II release 2010, Bruker AXS, Inc.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed fine focus tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD with Bruker Apex II detector'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            60626
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.754
_diffrn_reflns_theta_max         30.819
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5259
_reflns_number_gt                4834
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_max     0.990
_reflns_Friedel_fraction_full    1.000

_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       'Apex II release 2010, Bruker AXS, Inc.'
_computing_cell_refinement       'Apex II release 2010, Bruker AXS, Inc.'
_computing_data_reduction        'Apex II release 2010, Bruker AXS, Inc.'

_computing_structure_solution    
;

Sheldrick, G. M. (2015).  SHELXT.  Acta Cryst. A71, 3-8.

;
_computing_structure_refinement  'Shelxl-2016/6, Sheldrick, G. M.'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'SHELXL-2016/6, Sheldrick, G. M.'




_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)+(0.0416P)²+0.3040P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1965 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.039(12)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5259
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0771
_refine_ls_wR_factor_gt          0.0758
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
C1 C 0.19933(19) 0.59682(16) 0.92654(6) 0.0131(3) Uani 1 1 d . . . . .
H1 H 0.245027 0.619910 0.966615 0.016 Uiso 1 1 calc R U . . .
C2 C 0.2676(2) 0.45263(17) 0.90657(8) 0.0208(3) Uani 1 1 d . . . . .
H2A H 0.314233 0.456837 0.865969 0.025 Uiso 1 1 calc R U . . .
H2B H 0.357002 0.417369 0.933709 0.025 Uiso 1 1 calc R U . . .
C3 C 0.1056(2) 0.36101(17) 0.90936(9) 0.0222(3) Uani 1 1 d . . . . .
H3 H 0.116177 0.268547 0.888684 0.027 Uiso 1 1 calc R U . . .
C4 C 0.0518(2) 0.34966(18) 0.97450(8) 0.0258(4) Uani 1 1 d . . . . .
H4A H 0.151666 0.331016 1.000155 0.031 Uiso 1 1 calc R U . . .
H4B H -0.033508 0.273986 0.980147 0.031 Uiso 1 1 calc R U . . .
C5 C -0.0268(2) 0.49571(18) 0.98783(7) 0.0187(3) Uani 1 1 d . . . . .
H5A H -0.150293 0.488300 0.996713 0.022 Uiso 1 1 calc R U . . .
H5B H 0.031921 0.541855 1.021358 0.022 Uiso 1 1 calc R U . . .
C6 C 0.00424(18) 0.57542(15) 0.92990(6) 0.0117(3) Uani 1 1 d . . . . .
C7 C -0.0779(2) 0.71945(17) 0.92577(8) 0.0188(3) Uani 1 1 d . . . . .
H7A H -0.091039 0.760868 0.965612 0.023 Uiso 1 1 calc R U . . .
H7B H -0.192253 0.712321 0.907306 0.023 Uiso 1 1 calc R U . . .
C8 C -0.0315(2) 0.45982(16) 0.88283(7) 0.0172(3) Uani 1 1 d . . . . .
C9 C 0.0008(3) 0.4995(2) 0.81833(8) 0.0277(4) Uani 1 1 d . . . . .
H9A H -0.003676 0.414718 0.793775 0.042 Uiso 1 1 calc R U . . .
H9B H 0.113702 0.543127 0.814716 0.042 Uiso 1 1 calc R U . . .
H9C H -0.087020 0.565909 0.805187 0.042 Uiso 1 1 calc R U . . .
C10 C -0.2139(2) 0.4015(2) 0.88595(8) 0.0255(4) Uani 1 1 d . . . . .
H10A H -0.295516 0.476552 0.876739 0.038 Uiso 1 1 calc R U . . .
H10B H -0.236173 0.365760 0.925798 0.038 Uiso 1 1 calc R U . . .
H10C H -0.226752 0.325030 0.857314 0.038 Uiso 1 1 calc R U . . .
C11 C 0.39812(19) 0.76495(15) 0.88281(7) 0.0140(3) Uani 1 1 d . . . . .
C12 C 0.4370(2) 0.87782(15) 0.84069(6) 0.0136(3) Uani 1 1 d . . . . .
C13 C 0.5640(2) 0.99518(15) 0.85279(6) 0.0147(3) Uani 1 1 d . . . . .
H13 H 0.652935 0.975524 0.883412 0.018 Uiso 1 1 calc R U . . .
C14 C 0.4507(2) 1.12668(16) 0.86323(7) 0.0171(3) Uani 1 1 d . . . . .
H14A H 0.361120 1.107623 0.893040 0.021 Uiso 1 1 calc R U . . .
H14B H 0.520132 1.207887 0.876324 0.021 Uiso 1 1 calc R U . . .
C15 C 0.3714(2) 1.15354(17) 0.80164(7) 0.0210(3) Uani 1 1 d . . . . .
H15A H 0.404395 1.247122 0.786278 0.025 Uiso 1 1 calc R U . . .
H15B H 0.245256 1.147039 0.803027 0.025 Uiso 1 1 calc R U . . .
C16 C 0.4491(2) 1.03363(17) 0.76325(7) 0.0191(3) Uani 1 1 d . . . . .
H16 H 0.442786 1.046852 0.719502 0.023 Uiso 1 1 calc R U . . .
C17 C 0.3696(2) 0.90038(17) 0.78730(7) 0.0168(3) Uani 1 1 d . . . . .
C18 C 0.6296(2) 1.02278(17) 0.78989(7) 0.0182(3) Uani 1 1 d . . . . .
H18A H 0.696285 0.943259 0.773656 0.022 Uiso 1 1 calc R U . . .
H18B H 0.695290 1.111333 0.786546 0.022 Uiso 1 1 calc R U . . .
O1 O 0.09899(17) 0.95460(13) 0.91140(7) 0.0333(3) Uani 1 1 d . . . . .
O2 O -0.00039(17) 0.83389(17) 0.82246(6) 0.0338(3) Uani 1 1 d . . . . .
O3 O 0.50825(15) 0.71070(12) 0.91344(6) 0.0209(3) Uani 1 1 d . . . . .
S1 S 0.05944(5) 0.82584(4) 0.88166(2) 0.01917(10) Uani 1 1 d . . . . .
N1 N 0.23083(15) 0.71521(13) 0.88596(6) 0.0122(2) Uani 1 1 d . . . . .
H17 H 0.277(3) 0.848(2) 0.7692(8) 0.013(4) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.4744(19) . ?
C1 C2 1.540(2) . ?
C1 C6 1.542(2) . ?
C1 H1 1.0000 . ?
C2 C3 1.540(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.538(3) . ?
C3 C8 1.548(2) . ?
C3 H3 1.0000 . ?
C4 C5 1.549(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.535(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.516(2) . ?
C6 C8 1.557(2) . ?
C7 S1 1.7825(16) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.530(2) . ?
C8 C10 1.533(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O3 1.2208(19) . ?
C11 N1 1.3939(19) . ?
C11 C12 1.468(2) . ?
C12 C17 1.336(2) . ?
C12 C13 1.520(2) . ?
C13 C18 1.537(2) . ?
C13 C14 1.552(2) . ?
C13 H13 1.0000 . ?
C14 C15 1.548(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.558(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.513(2) . ?
C16 C18 1.539(3) . ?
C16 H16 1.0000 . ?
C17 H17 0.97(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
O1 S1 1.4317(14) . ?
O2 S1 1.4223(15) . ?
S1 N1 1.7077(13) . ?

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
N1 C1 C2 116.06(12) . . ?
N1 C1 C6 107.29(12) . . ?
C2 C1 C6 103.91(13) . . ?
N1 C1 H1 109.8 . . ?
C2 C1 H1 109.8 . . ?
C6 C1 H1 109.8 . . ?
C3 C2 C1 101.92(13) . . ?
C3 C2 H2A 111.4 . . ?
C1 C2 H2A 111.4 . . ?
C3 C2 H2B 111.4 . . ?
C1 C2 H2B 111.4 . . ?
H2A C2 H2B 109.3 . . ?
C4 C3 C2 107.73(15) . . ?
C4 C3 C8 103.03(13) . . ?
C2 C3 C8 102.18(13) . . ?
C4 C3 H3 114.2 . . ?
C2 C3 H3 114.2 . . ?
C8 C3 H3 114.2 . . ?
C3 C4 C5 103.45(13) . . ?
C3 C4 H4A 111.1 . . ?
C5 C4 H4A 111.1 . . ?
C3 C4 H4B 111.1 . . ?
C5 C4 H4B 111.1 . . ?
H4A C4 H4B 109.0 . . ?
C6 C5 C4 102.35(13) . . ?
C6 C5 H5A 111.3 . . ?
C4 C5 H5A 111.3 . . ?
C6 C5 H5B 111.3 . . ?
C4 C5 H5B 111.3 . . ?
H5A C5 H5B 109.2 . . ?
C7 C6 C5 115.61(13) . . ?
C7 C6 C1 107.30(12) . . ?
C5 C6 C1 105.30(12) . . ?
C7 C6 C8 121.32(13) . . ?
C5 C6 C8 102.00(12) . . ?
C1 C6 C8 103.73(12) . . ?
C6 C7 S1 106.98(10) . . ?
C6 C7 H7A 110.3 . . ?
S1 C7 H7A 110.3 . . ?
C6 C7 H7B 110.3 . . ?
S1 C7 H7B 110.3 . . ?
H7A C7 H7B 108.6 . . ?
C9 C8 C10 106.68(14) . . ?
C9 C8 C3 113.95(14) . . ?
C10 C8 C3 114.07(14) . . ?
C9 C8 C6 116.74(13) . . ?
C10 C8 C6 113.03(13) . . ?
C3 C8 C6 92.22(12) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C11 N1 119.37(14) . . ?
O3 C11 C12 122.15(14) . . ?
N1 C11 C12 118.43(13) . . ?
C17 C12 C11 128.58(15) . . ?
C17 C12 C13 107.64(13) . . ?
C11 C12 C13 123.76(13) . . ?
C12 C13 C18 100.18(12) . . ?
C12 C13 C14 104.22(13) . . ?
C18 C13 C14 101.20(12) . . ?
C12 C13 H13 116.3 . . ?
C18 C13 H13 116.3 . . ?
C14 C13 H13 116.3 . . ?
C15 C14 C13 103.00(12) . . ?
C15 C14 H14A 111.2 . . ?
C13 C14 H14A 111.2 . . ?
C15 C14 H14B 111.2 . . ?
C13 C14 H14B 111.2 . . ?
H14A C14 H14B 109.1 . . ?
C14 C15 C16 103.05(13) . . ?
C14 C15 H15A 111.2 . . ?
C16 C15 H15A 111.2 . . ?
C14 C15 H15B 111.2 . . ?
C16 C15 H15B 111.2 . . ?
H15A C15 H15B 109.1 . . ?
C17 C16 C18 100.35(13) . . ?
C17 C16 C15 104.63(13) . . ?
C18 C16 C15 100.85(13) . . ?
C17 C16 H16 116.2 . . ?
C18 C16 H16 116.2 . . ?
C15 C16 H16 116.2 . . ?
C12 C17 C16 107.35(14) . . ?
C12 C17 H17 126.4(11) . . ?
C16 C17 H17 125.8(11) . . ?
C13 C18 C16 93.93(12) . . ?
C13 C18 H18A 112.9 . . ?
C16 C18 H18A 112.9 . . ?
C13 C18 H18B 112.9 . . ?
C16 C18 H18B 112.9 . . ?
H18A C18 H18B 110.4 . . ?
O2 S1 O1 117.94(10) . . ?
O2 S1 N1 110.21(8) . . ?
O1 S1 N1 109.31(7) . . ?
O2 S1 C7 111.12(8) . . ?
O1 S1 C7 110.65(9) . . ?
N1 S1 C7 95.26(7) . . ?
C11 N1 C1 116.63(12) . . ?
C11 N1 S1 121.71(10) . . ?
C1 N1 S1 112.02(9) . . ?

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
N1 C1 C2 C3 -125.06(14) . . . . ?
C6 C1 C2 C3 -7.55(17) . . . . ?
C1 C2 C3 C4 -66.14(17) . . . . ?
C1 C2 C3 C8 41.98(16) . . . . ?
C2 C3 C4 C5 74.74(17) . . . . ?
C8 C3 C4 C5 -32.79(16) . . . . ?
C3 C4 C5 C6 -4.00(17) . . . . ?
C4 C5 C6 C7 172.95(14) . . . . ?
C4 C5 C6 C1 -68.82(15) . . . . ?
C4 C5 C6 C8 39.23(15) . . . . ?
N1 C1 C6 C7 -35.06(16) . . . . ?
C2 C1 C6 C7 -158.50(13) . . . . ?
N1 C1 C6 C5 -158.75(12) . . . . ?
C2 C1 C6 C5 77.81(15) . . . . ?
N1 C1 C6 C8 94.47(14) . . . . ?
C2 C1 C6 C8 -28.97(15) . . . . ?
C5 C6 C7 S1 147.66(12) . . . . ?
C1 C6 C7 S1 30.54(15) . . . . ?
C8 C6 C7 S1 -88.18(15) . . . . ?
C4 C3 C8 C9 175.06(14) . . . . ?
C2 C3 C8 C9 63.37(17) . . . . ?
C4 C3 C8 C10 -62.09(17) . . . . ?
C2 C3 C8 C10 -173.79(14) . . . . ?
C4 C3 C8 C6 54.40(14) . . . . ?
C2 C3 C8 C6 -57.29(14) . . . . ?
C7 C6 C8 C9 54.3(2) . . . . ?
C5 C6 C8 C9 -175.45(14) . . . . ?
C1 C6 C8 C9 -66.20(17) . . . . ?
C7 C6 C8 C10 -70.03(19) . . . . ?
C5 C6 C8 C10 60.25(17) . . . . ?
C1 C6 C8 C10 169.50(14) . . . . ?
C7 C6 C8 C3 172.59(14) . . . . ?
C5 C6 C8 C3 -57.13(13) . . . . ?
C1 C6 C8 C3 52.12(13) . . . . ?
O3 C11 C12 C17 143.00(18) . . . . ?
N1 C11 C12 C17 -34.5(2) . . . . ?
O3 C11 C12 C13 -38.7(2) . . . . ?
N1 C11 C12 C13 143.80(15) . . . . ?
C17 C12 C13 C18 -32.82(16) . . . . ?
C11 C12 C13 C18 148.56(14) . . . . ?
C17 C12 C13 C14 71.61(15) . . . . ?
C11 C12 C13 C14 -107.01(16) . . . . ?
C12 C13 C14 C15 -67.70(14) . . . . ?
C18 C13 C14 C15 35.96(15) . . . . ?
C13 C14 C15 C16 0.08(16) . . . . ?
C14 C15 C16 C17 67.87(16) . . . . ?
C14 C15 C16 C18 -35.96(15) . . . . ?
C11 C12 C17 C16 177.94(15) . . . . ?
C13 C12 C17 C16 -0.60(17) . . . . ?
C18 C16 C17 C12 33.75(16) . . . . ?
C15 C16 C17 C12 -70.45(17) . . . . ?
C12 C13 C18 C16 49.80(14) . . . . ?
C14 C13 C18 C16 -57.06(14) . . . . ?
C17 C16 C18 C13 -50.36(13) . . . . ?
C15 C16 C18 C13 56.88(13) . . . . ?
C6 C7 S1 O2 99.11(13) . . . . ?
C6 C7 S1 O1 -127.87(12) . . . . ?
C6 C7 S1 N1 -14.94(12) . . . . ?
O3 C11 N1 C1 -0.7(2) . . . . ?
C12 C11 N1 C1 176.87(13) . . . . ?
O3 C11 N1 S1 142.68(13) . . . . ?
C12 C11 N1 S1 -39.73(19) . . . . ?
C2 C1 N1 C11 -72.95(18) . . . . ?
C6 C1 N1 C11 171.43(13) . . . . ?
C2 C1 N1 S1 140.22(12) . . . . ?
C6 C1 N1 S1 24.60(15) . . . . ?
O2 S1 N1 C11 94.39(14) . . . . ?
O1 S1 N1 C11 -36.76(15) . . . . ?
C7 S1 N1 C11 -150.81(13) . . . . ?
O2 S1 N1 C1 -120.70(11) . . . . ?
O1 S1 N1 C1 108.15(12) . . . . ?
C7 S1 N1 C1 -5.90(12) . . . . ?

_refine_diff_density_max         0.295
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.044



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

data_mo_0417_ky_rl
_database_code_depnum_ccdc_archive 'CCDC 1859744'
_audit_update_record             
;
2018-08-01 deposited with the CCDC.
2018-09-25 downloaded from the CCDC.
;
_audit_creation_date             2017-06-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_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_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.9608(8)
_cell_length_b                   9.0050(9)
_cell_length_c                   11.9856(12)
_cell_angle_alpha                90
_cell_angle_beta                 105.827(2)
_cell_angle_gamma                90
_cell_volume                     826.64(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6808
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.66
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1200 before and 0.0557 after correction. The Ratio of minimum to maximum transmission is 0.8028. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             360
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'obtained by the evaporation in DCM/hexane solution'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12941
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.659
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.876
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                3381
_reflns_number_total             3792
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 1368 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3792
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0393
_refine_ls_restrained_S_all      1.053
_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)+(0.0397P)²+0.1700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0864
_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:
 C9(H9), C3(H3), C6(H6), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C13(H13A,H13B), C12(H12A,H12B), C10(H10A,H10B), C5(H5A,H5B),
 C4(H4A,H4B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.52212(8) 0.48364(7) 0.61805(6) 0.02487(18) Uani 1 1 d . . . . .
O3 O 0.1385(2) 0.4387(2) 0.74425(18) 0.0276(5) Uani 1 1 d . . . . .
O2 O 0.4128(3) 0.4734(3) 0.50304(17) 0.0447(6) Uani 1 1 d . . . . .
O1 O 0.6198(3) 0.6166(2) 0.6495(3) 0.0460(7) Uani 1 1 d . . . . .
N1 N 0.4056(3) 0.4486(2) 0.71369(19) 0.0187(5) Uani 1 1 d . . . . .
C8 C 0.2408(3) 0.5097(3) 0.7061(2) 0.0203(6) Uani 1 1 d . . . . .
C9 C 0.4384(3) 0.2970(3) 0.7617(2) 0.0177(5) Uani 1 1 d . . . . .
H9 H 0.353176 0.225846 0.712525 0.021 Uiso 1 1 calc R . . . .
C2 C 0.1962(3) 0.6575(3) 0.6569(2) 0.0212(6) Uani 1 1 d . . . . .
C14 C 0.6256(3) 0.2559(3) 0.7605(2) 0.0193(6) Uani 1 1 d . . . . .
C15 C 0.7386(4) 0.3002(4) 0.8842(3) 0.0263(6) Uani 1 1 d . . . . .
C3 C 0.0073(3) 0.7086(3) 0.6226(3) 0.0235(6) Uani 1 1 d . . . . .
H3 H -0.082411 0.629229 0.595372 0.028 Uiso 1 1 calc R . . . .
C1 C 0.2953(4) 0.7765(3) 0.6539(3) 0.0261(6) Uani 1 1 d . . . . .
H1 H 0.419211 0.779024 0.673195 0.031 Uiso 1 1 calc R . . . .
C18 C 0.6622(4) 0.3262(3) 0.6555(3) 0.0222(6) Uani 1 1 d . . . . .
H18A H 0.638466 0.254639 0.590297 0.027 Uiso 1 1 calc R . . . .
H18B H 0.786010 0.357203 0.673232 0.027 Uiso 1 1 calc R . . . .
C13 C 0.6314(4) 0.0853(3) 0.7666(3) 0.0277(7) Uani 1 1 d . . . . .
H13A H 0.741177 0.046363 0.754120 0.033 Uiso 1 1 calc R . . . .
H13B H 0.530889 0.040782 0.708753 0.033 Uiso 1 1 calc R . . . .
C12 C 0.6218(4) 0.0548(4) 0.8916(3) 0.0321(7) Uani 1 1 d . . . . .
H12A H 0.514177 -0.000320 0.891394 0.038 Uiso 1 1 calc R . . . .
H12B H 0.724419 -0.002826 0.935651 0.038 Uiso 1 1 calc R . . . .
C6 C 0.1734(4) 0.9064(3) 0.6140(3) 0.0292(7) Uani 1 1 d . . . . .
H6 H 0.221508 0.991795 0.579143 0.035 Uiso 1 1 calc R . . . .
C10 C 0.4405(4) 0.2795(3) 0.8898(2) 0.0250(6) Uani 1 1 d . . . . .
H10A H 0.428634 0.376715 0.925460 0.030 Uiso 1 1 calc R . . . .
H10B H 0.346005 0.212641 0.898337 0.030 Uiso 1 1 calc R . . . .
C5 C 0.0996(4) 0.9437(3) 0.7174(3) 0.0353(8) Uani 1 1 d . . . . .
H5A H 0.028549 1.035515 0.702693 0.042 Uiso 1 1 calc R . . . .
H5B H 0.194449 0.955614 0.789979 0.042 Uiso 1 1 calc R . . . .
C17 C 0.7494(4) 0.4660(4) 0.9124(3) 0.0350(7) Uani 1 1 d . . . . .
H17A H 0.814484 0.516722 0.864994 0.053 Uiso 1 1 calc GR . . . .
H17B H 0.809392 0.480240 0.994709 0.053 Uiso 1 1 calc GR . . . .
H17C H 0.631302 0.507389 0.895659 0.053 Uiso 1 1 calc GR . . . .
C11 C 0.6207(4) 0.2111(4) 0.9434(3) 0.0286(7) Uani 1 1 d . . . . .
H11 H 0.659092 0.214127 1.030052 0.034 Uiso 1 1 calc R . . . .
C4 C -0.0148(4) 0.8060(3) 0.7236(3) 0.0294(7) Uani 1 1 d . . . . .
H4A H 0.027821 0.754045 0.798782 0.035 Uiso 1 1 calc R . . . .
H4B H -0.138426 0.834448 0.712285 0.035 Uiso 1 1 calc R . . . .
C7 C 0.0156(4) 0.8269(4) 0.5343(3) 0.0323(7) Uani 1 1 d . . . . .
H7A H -0.090248 0.890007 0.512968 0.039 Uiso 1 1 calc R . . . .
H7B H 0.040089 0.785666 0.463829 0.039 Uiso 1 1 calc R . . . .
C16 C 0.9268(4) 0.2427(4) 0.9113(3) 0.0368(8) Uani 1 1 d . . . . .
H16A H 0.925691 0.134812 0.900452 0.055 Uiso 1 1 calc GR . . . .
H16B H 0.988584 0.266660 0.991844 0.055 Uiso 1 1 calc GR . . . .
H16C H 0.986502 0.289891 0.859097 0.055 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 1.418(2) . ?
S1 O1 1.421(2) . ?
S1 N1 1.689(2) . ?
S1 C18 1.784(3) . ?
O3 C8 1.218(3) . ?
N1 C8 1.402(3) . ?
N1 C9 1.477(3) . ?
C8 C2 1.460(4) . ?
C9 H9 1.0000 . ?
C9 C14 1.540(4) . ?
C9 C10 1.539(4) . ?
C2 C3 1.518(4) . ?
C2 C1 1.338(4) . ?
C14 C15 1.562(4) . ?
C14 C18 1.506(4) . ?
C14 C13 1.538(4) . ?
C15 C17 1.528(5) . ?
C15 C11 1.547(4) . ?
C15 C16 1.534(4) . ?
C3 H3 1.0000 . ?
C3 C4 1.543(4) . ?
C3 C7 1.515(4) . ?
C1 H1 0.9500 . ?
C1 C6 1.512(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C12 1.545(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C11 1.539(5) . ?
C6 H6 1.0000 . ?
C6 C5 1.546(4) . ?
C6 C7 1.533(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.532(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C4 1.552(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C11 H11 1.0000 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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 117.30(17) . . ?
O2 S1 N1 110.01(12) . . ?
O2 S1 C18 111.61(16) . . ?
O1 S1 N1 109.84(13) . . ?
O1 S1 C18 110.11(13) . . ?
N1 S1 C18 95.89(12) . . ?
C8 N1 S1 124.05(18) . . ?
C8 N1 C9 116.8(2) . . ?
C9 N1 S1 111.41(17) . . ?
O3 C8 N1 118.6(2) . . ?
O3 C8 C2 121.1(2) . . ?
N1 C8 C2 120.3(2) . . ?
N1 C9 H9 110.1 . . ?
N1 C9 C14 106.7(2) . . ?
N1 C9 C10 115.8(2) . . ?
C14 C9 H9 110.1 . . ?
C10 C9 H9 110.1 . . ?
C10 C9 C14 103.8(2) . . ?
C8 C2 C3 120.0(2) . . ?
C1 C2 C8 131.4(3) . . ?
C1 C2 C3 107.3(2) . . ?
C9 C14 C15 103.8(2) . . ?
C18 C14 C9 108.4(2) . . ?
C18 C14 C15 119.5(2) . . ?
C18 C14 C13 116.7(2) . . ?
C13 C14 C9 104.8(2) . . ?
C13 C14 C15 102.0(2) . . ?
C17 C15 C14 116.3(2) . . ?
C17 C15 C11 114.2(3) . . ?
C17 C15 C16 106.9(3) . . ?
C11 C15 C14 92.2(2) . . ?
C16 C15 C14 113.1(2) . . ?
C16 C15 C11 114.0(3) . . ?
C2 C3 H3 116.0 . . ?
C2 C3 C4 106.0(2) . . ?
C4 C3 H3 116.0 . . ?
C7 C3 C2 100.0(2) . . ?
C7 C3 H3 116.0 . . ?
C7 C3 C4 100.6(2) . . ?
C2 C1 H1 126.4 . . ?
C2 C1 C6 107.2(2) . . ?
C6 C1 H1 126.4 . . ?
S1 C18 H18A 110.3 . . ?
S1 C18 H18B 110.3 . . ?
C14 C18 S1 107.09(18) . . ?
C14 C18 H18A 110.3 . . ?
C14 C18 H18B 110.3 . . ?
H18A C18 H18B 108.6 . . ?
C14 C13 H13A 111.3 . . ?
C14 C13 H13B 111.3 . . ?
C14 C13 C12 102.4(2) . . ?
H13A C13 H13B 109.2 . . ?
C12 C13 H13A 111.3 . . ?
C12 C13 H13B 111.3 . . ?
C13 C12 H12A 111.0 . . ?
C13 C12 H12B 111.0 . . ?
H12A C12 H12B 109.0 . . ?
C11 C12 C13 103.6(2) . . ?
C11 C12 H12A 111.0 . . ?
C11 C12 H12B 111.0 . . ?
C1 C6 H6 116.2 . . ?
C1 C6 C5 105.4(3) . . ?
C1 C6 C7 100.5(2) . . ?
C5 C6 H6 116.2 . . ?
C7 C6 H6 116.2 . . ?
C7 C6 C5 100.1(2) . . ?
C9 C10 H10A 111.3 . . ?
C9 C10 H10B 111.3 . . ?
H10A C10 H10B 109.2 . . ?
C11 C10 C9 102.3(2) . . ?
C11 C10 H10A 111.3 . . ?
C11 C10 H10B 111.3 . . ?
C6 C5 H5A 111.2 . . ?
C6 C5 H5B 111.2 . . ?
C6 C5 C4 102.8(2) . . ?
H5A C5 H5B 109.1 . . ?
C4 C5 H5A 111.2 . . ?
C4 C5 H5B 111.2 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C11 H11 114.2 . . ?
C12 C11 C15 102.6(2) . . ?
C12 C11 H11 114.2 . . ?
C10 C11 C15 102.4(2) . . ?
C10 C11 C12 107.8(3) . . ?
C10 C11 H11 114.2 . . ?
C3 C4 C5 102.9(2) . . ?
C3 C4 H4A 111.2 . . ?
C3 C4 H4B 111.2 . . ?
C5 C4 H4A 111.2 . . ?
C5 C4 H4B 111.2 . . ?
H4A C4 H4B 109.1 . . ?
C3 C7 C6 94.5(2) . . ?
C3 C7 H7A 112.8 . . ?
C3 C7 H7B 112.8 . . ?
C6 C7 H7A 112.8 . . ?
C6 C7 H7B 112.8 . . ?
H7A C7 H7B 110.3 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_olex2_exptl_crystal_mounting_method 'mounted with the 20-um-looped base'
_olex2_submission_special_instructions 'No special instructions were received'
