# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_hyp01
_audit_block_doi                 10.5517/ccdc.csd.cc1q0d6b
_database_code_depnum_ccdc_archive 'CCDC 1579301'
_audit_update_record             
;
2017-10-11 deposited with the CCDC.	2019-04-09 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H23 N O5 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         353.42

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.0877(11)
_cell_length_b                   10.8073(14)
_cell_length_c                   26.052(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.948(6)
_cell_angle_gamma                90
_cell_volume                     1709.9(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7462
_cell_measurement_theta_min      2.3546
_cell_measurement_theta_max      25.0410
_cell_measurement_temperature    293.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.260
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752

_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.95

_exptl_special_details           
;
;

_diffrn_ambient_temperature      293.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            17928
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_theta_min         2.45
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30

_refine_special_details          
;
;

_reflns_number_total             3010
_reflns_number_gt                2600
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0943
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_number_reflns         3010
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0388P)²+0.8083P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.326
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.68828(8) 0.41773(4) 0.36221(2) 0.03680(15) Uani d . . . 1 . .
N N1 0.6775(2) 0.50151(14) 0.30809(5) 0.0336(3) Uani d . . . 1 . .
O O1 0.7518(2) 0.65803(12) 0.25755(5) 0.0377(3) Uani d . . . 1 . .
O O2 0.9814(2) 0.62708(14) 0.32693(5) 0.0484(4) Uani d . . . 1 . .
O O3 0.3586(3) 0.75126(15) 0.28939(6) 0.0559(4) Uani d . . . 1 . .
H H3 0.2481 0.7212 0.3007 0.084 Uiso calc U . R 1 . .
O O4 0.5154(3) 0.32977(12) 0.35265(5) 0.0501(4) Uani d . . . 1 . .
O O5 0.9097(2) 0.37819(14) 0.37336(6) 0.0533(4) Uani d . . . 1 . .
C C1 0.5833(3) 0.57352(16) 0.17876(7) 0.0319(4) Uani d . . . 1 . .
H H1 0.6388 0.6482 0.1627 0.038 Uiso calc U . R 1 . .
C C2 0.7611(3) 0.47395(19) 0.17547(7) 0.0424(5) Uani d . . . 1 . .
H H2A 0.895 0.5009 0.1946 0.051 Uiso calc U . R 1 . .
H H2B 0.7124 0.3981 0.1911 0.051 Uiso calc U . R 1 . .
C C3 0.8094(4) 0.4487(2) 0.11975(8) 0.0524(5) Uani d . . . 1 . .
H H3A 0.8714 0.5223 0.1051 0.063 Uiso calc U . R 1 . .
H H3B 0.9171 0.3827 0.1187 0.063 Uiso calc U . R 1 . .
C C4 0.6018(4) 0.4120(2) 0.08803(9) 0.0581(6) Uani d . . . 1 . .
H H4A 0.5491 0.3334 0.1003 0.07 Uiso calc U . R 1 . .
H H4B 0.635 0.4015 0.0524 0.07 Uiso calc U . R 1 . .
C C5 0.4232(4) 0.5088(2) 0.09128(8) 0.0541(6) Uani d . . . 1 . .
H H5A 0.2899 0.4801 0.0724 0.065 Uiso calc U . R 1 . .
H H5B 0.4692 0.5846 0.0752 0.065 Uiso calc U . R 1 . .
C C6 0.3739(3) 0.5358(2) 0.14702(7) 0.0416(5) Uani d . . . 1 . .
H H6A 0.2663 0.6019 0.1477 0.05 Uiso calc U . R 1 . .
H H6B 0.3117 0.4627 0.162 0.05 Uiso calc U . R 1 . .
C C7 0.5409(3) 0.60800(16) 0.23438(7) 0.0317(4) Uani d . . . 1 . .
C C8 0.8187(3) 0.59883(17) 0.30030(7) 0.0339(4) Uani d . . . 1 . .
C C9 0.4906(3) 0.49815(17) 0.26946(7) 0.0353(4) Uani d . . . 1 . .
H H9A 0.3521 0.5098 0.2851 0.042 Uiso calc U . R 1 . .
H H9B 0.4859 0.4207 0.2506 0.042 Uiso calc U . R 1 . .
C C10 0.3744(3) 0.71223(18) 0.23805(7) 0.0422(5) Uani d . . . 1 . .
H H10A 0.418 0.7818 0.2175 0.051 Uiso calc U . R 1 . .
H H10B 0.2312 0.6842 0.2241 0.051 Uiso calc U . R 1 . .
C C11 0.6187(3) 0.52318(17) 0.40971(6) 0.0335(4) Uani d . . . 1 . .
C C12 0.4076(3) 0.5707(2) 0.40797(7) 0.0454(5) Uani d . . . 1 . .
H H12 0.3015 0.5445 0.3829 0.054 Uiso calc U . R 1 . .
C C13 0.3574(4) 0.6575(2) 0.44406(8) 0.0496(5) Uani d . . . 1 . .
H H13 0.2171 0.6919 0.4424 0.06 Uiso calc U . R 1 . .
C C14 0.5107(4) 0.69513(18) 0.48282(7) 0.0442(5) Uani d . . . 1 . .
C C15 0.7180(4) 0.6432(2) 0.48446(8) 0.0498(5) Uani d . . . 1 . .
H H15 0.8217 0.6656 0.5107 0.06 Uiso calc U . R 1 . .
C C16 0.7748(3) 0.55853(19) 0.44796(7) 0.0431(5) Uani d . . . 1 . .
H H16 0.9163 0.5257 0.4491 0.052 Uiso calc U . R 1 . .
C C17 0.4520(5) 0.7914(2) 0.52132(9) 0.0689(7) Uani d . . . 1 . .
H H17A 0.4732 0.8724 0.5074 0.103 Uiso calc U . R 1 . .
H H17B 0.5446 0.7816 0.5524 0.103 Uiso calc U . R 1 . .
H H17C 0.3007 0.7816 0.5288 0.103 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O5 . 1.4246(15) ?
S1 O4 . 1.4273(14) ?
S1 N1 . 1.6732(15) ?
S1 C11 . 1.7553(18) ?
N1 C8 . 1.382(2) ?
N1 C9 . 1.467(2) ?
O1 C8 . 1.324(2) ?
O1 C7 . 1.483(2) ?
O2 C8 . 1.209(2) ?
O3 C10 . 1.412(2) ?
O3 H3 . 0.82 ?
C1 C6 . 1.526(3) ?
C1 C2 . 1.533(2) ?
C1 C7 . 1.535(2) ?
C1 H1 . 0.98 ?
C2 C3 . 1.525(3) ?
C2 H2A . 0.97 ?
C2 H2B . 0.97 ?
C3 C4 . 1.514(3) ?
C3 H3A . 0.97 ?
C3 H3B . 0.97 ?
C4 C5 . 1.515(3) ?
C4 H4A . 0.97 ?
C4 H4B . 0.97 ?
C5 C6 . 1.531(3) ?
C5 H5A . 0.97 ?
C5 H5B . 0.97 ?
C6 H6A . 0.97 ?
C6 H6B . 0.97 ?
C7 C10 . 1.522(3) ?
C7 C9 . 1.542(2) ?
C9 H9A . 0.97 ?
C9 H9B . 0.97 ?
C10 H10A . 0.97 ?
C10 H10B . 0.97 ?
C11 C12 . 1.382(3) ?
C11 C16 . 1.382(3) ?
C12 C13 . 1.378(3) ?
C12 H12 . 0.93 ?
C13 C14 . 1.387(3) ?
C13 H13 . 0.93 ?
C14 C15 . 1.380(3) ?
C14 C17 . 1.505(3) ?
C15 C16 . 1.380(3) ?
C15 H15 . 0.93 ?
C16 H16 . 0.93 ?
C17 H17A . 0.96 ?
C17 H17B . 0.96 ?
C17 H17C . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O5 S1 O4 . . 120.78(9) ?
O5 S1 N1 . . 108.41(8) ?
O4 S1 N1 . . 103.15(8) ?
O5 S1 C11 . . 108.77(9) ?
O4 S1 C11 . . 110.17(9) ?
N1 S1 C11 . . 104.20(8) ?
C8 N1 C9 . . 112.28(14) ?
C8 N1 S1 . . 123.14(12) ?
C9 N1 S1 . . 123.27(12) ?
C8 O1 C7 . . 111.96(13) ?
C10 O3 H3 . . 109.5 ?
C6 C1 C2 . . 110.43(15) ?
C6 C1 C7 . . 112.82(14) ?
C2 C1 C7 . . 112.87(14) ?
C6 C1 H1 . . 106.8 ?
C2 C1 H1 . . 106.8 ?
C7 C1 H1 . . 106.8 ?
C3 C2 C1 . . 111.23(16) ?
C3 C2 H2A . . 109.4 ?
C1 C2 H2A . . 109.4 ?
C3 C2 H2B . . 109.4 ?
C1 C2 H2B . . 109.4 ?
H2A C2 H2B . . 108.0 ?
C4 C3 C2 . . 110.97(17) ?
C4 C3 H3A . . 109.4 ?
C2 C3 H3A . . 109.4 ?
C4 C3 H3B . . 109.4 ?
C2 C3 H3B . . 109.4 ?
H3A C3 H3B . . 108.0 ?
C3 C4 C5 . . 111.34(19) ?
C3 C4 H4A . . 109.4 ?
C5 C4 H4A . . 109.4 ?
C3 C4 H4B . . 109.4 ?
C5 C4 H4B . . 109.4 ?
H4A C4 H4B . . 108.0 ?
C4 C5 C6 . . 111.90(18) ?
C4 C5 H5A . . 109.2 ?
C6 C5 H5A . . 109.2 ?
C4 C5 H5B . . 109.2 ?
C6 C5 H5B . . 109.2 ?
H5A C5 H5B . . 107.9 ?
C1 C6 C5 . . 110.73(16) ?
C1 C6 H6A . . 109.5 ?
C5 C6 H6A . . 109.5 ?
C1 C6 H6B . . 109.5 ?
C5 C6 H6B . . 109.5 ?
H6A C6 H6B . . 108.1 ?
O1 C7 C10 . . 105.43(14) ?
O1 C7 C1 . . 106.00(13) ?
C10 C7 C1 . . 113.25(14) ?
O1 C7 C9 . . 103.96(13) ?
C10 C7 C9 . . 111.86(15) ?
C1 C7 C9 . . 115.19(14) ?
O2 C8 O1 . . 123.59(17) ?
O2 C8 N1 . . 126.97(18) ?
O1 C8 N1 . . 109.43(15) ?
N1 C9 C7 . . 102.20(13) ?
N1 C9 H9A . . 111.3 ?
C7 C9 H9A . . 111.3 ?
N1 C9 H9B . . 111.3 ?
C7 C9 H9B . . 111.3 ?
H9A C9 H9B . . 109.2 ?
O3 C10 C7 . . 111.69(16) ?
O3 C10 H10A . . 109.3 ?
C7 C10 H10A . . 109.3 ?
O3 C10 H10B . . 109.3 ?
C7 C10 H10B . . 109.3 ?
H10A C10 H10B . . 107.9 ?
C12 C11 C16 . . 120.81(18) ?
C12 C11 S1 . . 119.15(14) ?
C16 C11 S1 . . 120.03(15) ?
C13 C12 C11 . . 118.70(18) ?
C13 C12 H12 . . 120.6 ?
C11 C12 H12 . . 120.6 ?
C12 C13 C14 . . 121.78(19) ?
C12 C13 H13 . . 119.1 ?
C14 C13 H13 . . 119.1 ?
C15 C14 C13 . . 118.11(19) ?
C15 C14 C17 . . 121.3(2) ?
C13 C14 C17 . . 120.6(2) ?
C14 C15 C16 . . 121.35(19) ?
C14 C15 H15 . . 119.3 ?
C16 C15 H15 . . 119.3 ?
C15 C16 C11 . . 119.18(19) ?
C15 C16 H16 . . 120.4 ?
C11 C16 H16 . . 120.4 ?
C14 C17 H17A . . 109.5 ?
C14 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C14 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?

