# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_mp180814S1
_database_code_depnum_ccdc_archive 'CCDC 1976913'
loop_
_audit_author_name
_audit_author_address
'Ales Ruzicka'
;University of Pardubice
Czech Republic
;
_audit_update_record             
;
2020-01-11 deposited with the CCDC.	2020-06-30 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         'C17 H21 N O6 S'
_chemical_formula_sum            'C17 H21 N O6 S'
_chemical_formula_weight         367.41

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 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   12.909(2)
_cell_length_b                   9.8608(13)
_cell_length_c                   14.025(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.066(6)
_cell_angle_gamma                90
_cell_volume                     1775.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    45702
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.592
_exptl_crystal_size_mid          0.466
_exptl_crystal_size_min          0.404
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6800
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_absorpt_special_details   
;
The ratio of minimum to maximum
apparent transmission was 0.912;
;



_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            45702
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.530
_diffrn_reflns_theta_max         27.529
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4079
_reflns_number_gt                3520
_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 Instrument Service vV6.2.3'
_computing_cell_refinement       'APEX3 v2016.5-0 (Bruker AXS)'
_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    'Platon (Spek, 2009)'
_computing_publication_material  'Platon (Spek, 2009)'
_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)+(0.0387P)²+0.8769P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0164(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4079
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0858
_refine_ls_wR_factor_gt          0.0795
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
S1 S 0.49490(2) 0.28797(3) 0.24676(2) 0.02130(10) Uani 1 1 d . . . . .
O1 O 0.45583(8) 0.41931(9) 0.21735(7) 0.0286(2) Uani 1 1 d . . . . .
N1 N 0.41226(8) 0.17861(10) 0.19649(7) 0.0204(2) Uani 1 1 d . . . . .
C1 C 0.30830(9) 0.21452(13) 0.15236(9) 0.0199(3) Uani 1 1 d . . . . .
H1 H 0.2947 0.3130 0.1625 0.024 Uiso 1 1 calc R U . . .
O2 O 0.59693(7) 0.24703(11) 0.22648(7) 0.0299(2) Uani 1 1 d . . . . .
C2 C 0.30271(9) 0.18345(12) 0.04461(9) 0.0187(2) Uani 1 1 d . . . . .
H2 H 0.2278 0.1827 0.0179 0.022 Uiso 1 1 calc R U . . .
C3 C 0.34912(9) 0.04635(13) 0.02583(9) 0.0196(2) Uani 1 1 d . . . . .
O3 O 0.23085(7) 0.13567(10) 0.18930(6) 0.0254(2) Uani 1 1 d . . . . .
C4 C 0.40827(10) -0.02025(13) 0.09424(9) 0.0214(3) Uani 1 1 d . . . . .
H4 H 0.4328 -0.1078 0.0794 0.026 Uiso 1 1 calc R U . . .
O4 O 0.44274(8) 0.29248(10) -0.02969(7) 0.0307(2) Uani 1 1 d . . . . .
O5 O 0.29697(7) 0.40886(10) -0.01061(8) 0.0308(2) Uani 1 1 d . . . . .
C5 C 0.43842(10) 0.03427(13) 0.19272(9) 0.0229(3) Uani 1 1 d . . . . .
H5A H 0.4012 -0.0163 0.2397 0.027 Uiso 1 1 calc R U . . .
H5B H 0.5142 0.0219 0.2100 0.027 Uiso 1 1 calc R U . . .
C6 C 0.21786(12) 0.16847(17) 0.28696(10) 0.0340(3) Uani 1 1 d . . . . .
H6A H 0.2067 0.2663 0.2927 0.051 Uiso 1 1 calc R U . . .
H6B H 0.2805 0.1419 0.3284 0.051 Uiso 1 1 calc R U . . .
H6C H 0.1575 0.1196 0.3065 0.051 Uiso 1 1 calc R U . . .
O6 O 0.47955(9) 0.20657(11) 0.66039(7) 0.0332(2) Uani 1 1 d . . . . .
C7 C 0.35727(10) 0.29794(13) -0.00343(9) 0.0209(3) Uani 1 1 d . . . . .
C8 C 0.34262(14) 0.52865(16) -0.04954(14) 0.0434(4) Uani 1 1 d . . . . .
H8A H 0.3671 0.5065 -0.1115 0.065 Uiso 1 1 calc R U . . .
H8B H 0.4015 0.5597 -0.0051 0.065 Uiso 1 1 calc R U . . .
H8C H 0.2901 0.6006 -0.0583 0.065 Uiso 1 1 calc R U . . .
C9 C 0.33026(10) -0.01136(14) -0.07068(9) 0.0254(3) Uani 1 1 d . . . . .
H9 H 0.3593 -0.0982 -0.0804 0.031 Uiso 1 1 calc R U . . .
C10 C 0.27630(12) 0.04645(17) -0.14605(10) 0.0321(3) Uani 1 1 d . . . . .
H10A H 0.2458 0.1333 -0.1398 0.039 Uiso 1 1 calc R U . . .
H10B H 0.2683 0.0009 -0.2061 0.039 Uiso 1 1 calc R U . . .
C11 C 0.49160(10) 0.27292(13) 0.37125(9) 0.0208(3) Uani 1 1 d . . . . .
C12 C 0.55304(10) 0.17366(14) 0.42063(10) 0.0248(3) Uani 1 1 d . . . . .
H12 H 0.5983 0.1188 0.3878 0.030 Uiso 1 1 calc R U . . .
C13 C 0.54750(10) 0.15585(14) 0.51764(10) 0.0263(3) Uani 1 1 d . . . . .
H13 H 0.5896 0.0891 0.5517 0.032 Uiso 1 1 calc R U . . .
C14 C 0.48052(11) 0.23531(14) 0.56572(9) 0.0242(3) Uani 1 1 d . . . . .
C15 C 0.42007(11) 0.33559(14) 0.51675(10) 0.0261(3) Uani 1 1 d . . . . .
H15 H 0.3752 0.3908 0.5498 0.031 Uiso 1 1 calc R U . . .
C16 C 0.42600(11) 0.35410(13) 0.41898(9) 0.0248(3) Uani 1 1 d . . . . .
H16 H 0.3852 0.4222 0.3850 0.030 Uiso 1 1 calc R U . . .
C17 C 0.41339(14) 0.28624(16) 0.71408(10) 0.0360(3) Uani 1 1 d . . . . .
H17A H 0.4318 0.3823 0.7095 0.054 Uiso 1 1 calc R U . . .
H17B H 0.4225 0.2579 0.7814 0.054 Uiso 1 1 calc R U . . .
H17C H 0.3406 0.2731 0.6881 0.054 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 1.4345(10) . ?
S1 O2 1.4346(10) . ?
S1 N1 1.6246(11) . ?
S1 C11 1.7573(13) . ?
N1 C1 1.4608(16) . ?
N1 C5 1.4650(16) . ?
C1 O3 1.4079(15) . ?
C1 C2 1.5363(17) . ?
C1 H1 1.0000 . ?
C2 C3 1.5131(17) . ?
C2 C7 1.5248(17) . ?
C2 H2 1.0000 . ?
C3 C4 1.3341(18) . ?
C3 C9 1.4648(17) . ?
O3 C6 1.4342(16) . ?
C4 C5 1.4949(18) . ?
C4 H4 0.9500 . ?
O4 C7 1.2008(16) . ?
O5 C7 1.3401(16) . ?
O5 C8 1.4521(17) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
O6 C14 1.3591(16) . ?
O6 C17 1.4316(18) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.331(2) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9500 . ?
C10 H10B 0.9500 . ?
C11 C16 1.3878(18) . ?
C11 C12 1.3967(19) . ?
C12 C13 1.3812(19) . ?
C12 H12 0.9500 . ?
C13 C14 1.3927(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.3947(19) . ?
C15 C16 1.3935(19) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 119.96(6) . . ?
O1 S1 N1 106.24(6) . . ?
O2 S1 N1 107.57(6) . . ?
O1 S1 C11 108.49(6) . . ?
O2 S1 C11 107.00(6) . . ?
N1 S1 C11 106.94(6) . . ?
C1 N1 C5 115.16(10) . . ?
C1 N1 S1 123.69(8) . . ?
C5 N1 S1 121.15(9) . . ?
O3 C1 N1 111.51(10) . . ?
O3 C1 C2 106.89(10) . . ?
N1 C1 C2 108.30(10) . . ?
O3 C1 H1 110.0 . . ?
N1 C1 H1 110.0 . . ?
C2 C1 H1 110.0 . . ?
C3 C2 C7 112.01(10) . . ?
C3 C2 C1 111.78(10) . . ?
C7 C2 C1 108.13(10) . . ?
C3 C2 H2 108.3 . . ?
C7 C2 H2 108.3 . . ?
C1 C2 H2 108.3 . . ?
C4 C3 C9 119.99(12) . . ?
C4 C3 C2 121.45(11) . . ?
C9 C3 C2 118.54(11) . . ?
C1 O3 C6 112.71(10) . . ?
C3 C4 C5 124.11(12) . . ?
C3 C4 H4 117.9 . . ?
C5 C4 H4 117.9 . . ?
C7 O5 C8 115.89(11) . . ?
N1 C5 C4 110.13(10) . . ?
N1 C5 H5A 109.6 . . ?
C4 C5 H5A 109.6 . . ?
N1 C5 H5B 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
O3 C6 H6A 109.5 . . ?
O3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C14 O6 C17 117.84(11) . . ?
O4 C7 O5 123.98(12) . . ?
O4 C7 C2 125.78(12) . . ?
O5 C7 C2 110.23(11) . . ?
O5 C8 H8A 109.5 . . ?
O5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C3 126.12(13) . . ?
C10 C9 H9 116.9 . . ?
C3 C9 H9 116.9 . . ?
C9 C10 H10A 120.0 . . ?
C9 C10 H10B 120.0 . . ?
H10A C10 H10B 120.0 . . ?
C16 C11 C12 120.57(12) . . ?
C16 C11 S1 120.71(10) . . ?
C12 C11 S1 118.67(10) . . ?
C13 C12 C11 119.46(12) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 120.32(12) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
O6 C14 C13 115.22(12) . . ?
O6 C14 C15 124.51(13) . . ?
C13 C14 C15 120.27(12) . . ?
C16 C15 C14 119.44(12) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C11 C16 C15 119.93(12) . . ?
C11 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
O6 C17 H17A 109.5 . . ?
O6 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O6 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_refine_diff_density_max         0.323
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.045



