# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_rvo_01092024_autored
_database_code_depnum_ccdc_archive 'CCDC 2385171'
loop_
_audit_author_name
_audit_author_address
'Gonzalo Campillo-Alvarado'
;Reed College
United States of America
;
_audit_update_record             
;
2024-09-19 deposited with the CCDC.	2025-01-27 downloaded from the CCDC.
;
_audit_creation_date             2024-08-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H23 N O5 S'
_chemical_formula_sum            'C16 H23 N O5 S'
_chemical_formula_weight         341.41
_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   7.4892(3)
_cell_length_b                   12.0747(5)
_cell_length_c                   18.9252(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.818(5)
_cell_angle_gamma                90
_cell_volume                     1691.17(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3561
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      30.4380
_cell_measurement_theta_min      2.1670
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.882
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.763
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.121a (Rigaku Oxford Diffraction, 2024)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             728
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.0306
-1 0 1 0.0282
-1 0 2 0.0249
1 0 -2 0.0301
0 0 -1 0.0457
0 0 1 0.0765
0 1 0 0.3229
0 -1 0 0.2722
-1 0 -1 0.0358
0 2 -1 0.3152
0 -2 1 0.2637
1 -2 -1 0.2218
2 0 -1 0.0275

_exptl_crystal_size_max          0.595
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.055
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_unetI/netI     0.0635
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9970
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.178
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      8.00  33.00   0.50   45.00    --   20.00  54.00 120.00   50
  2  ω    -71.00 107.00   0.50   45.00    --   20.00  54.00  30.00  356
  3  ω    -64.00  29.00   0.50   45.00    --   20.00  54.00 -30.00  186
  4  ω     59.00 105.00   0.50   45.00    --   20.00  54.00 -30.00   92
  5  ω    -13.00  13.00   0.50   45.00    --   20.00  54.00 -60.00   52
  6  ω    -73.00 -29.00   0.50   45.00    --   20.00  54.00-180.00   88
  7  ω      5.00  30.00   0.50   45.00    --   20.00  54.00-180.00   50
  8  ω     83.00 108.00   0.50   45.00    --   20.00  54.00-180.00   50
  9  ω    -66.00 -41.00   0.50   45.00    --   20.00  54.00 120.00   50
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2231
_reflns_number_total             2963
_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 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.104a 64-bit (release 22-12-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.430
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2963
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0597
_refine_ls_restrained_S_all      1.102
_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)+(0.0983P)²+0.8826P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1715
_refine_ls_wR_factor_ref         0.1807
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3)
1.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C13(H13A,H13B)
1.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C6(H6), C7(H7)
1.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C11(H11A,H11B,H11C), C14(H14A,H14B,
 H14C)
1.e Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_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 0.51350(10) 0.55494(6) 0.75792(4) 0.0189(3) Uani 1 1 d . . . . .
O1 O 0.4723(3) 0.66359(17) 0.78078(12) 0.0248(5) Uani 1 1 d . . . . .
O2 O 0.6290(3) 0.54310(18) 0.70467(12) 0.0269(6) Uani 1 1 d . . . . .
O3 O 0.2637(4) 0.54347(19) 0.57985(13) 0.0355(6) Uani 1 1 d . . . . .
O4 O 0.2884(4) 0.36510(19) 0.55224(12) 0.0372(7) Uani 1 1 d . . . . .
N1 N 0.3282(3) 0.4936(2) 0.72593(13) 0.0173(6) Uani 1 1 d . . . . .
C5 C 0.6150(4) 0.4830(3) 0.83495(16) 0.0190(7) Uani 1 1 d . . . . .
C1 C 0.3267(4) 0.4042(2) 0.67300(16) 0.0187(7) Uani 1 1 d . . . . .
H1 H 0.444861 0.364052 0.680596 0.022 Uiso 1 1 calc R U . . .
C4 C 0.1554(4) 0.5000(3) 0.75712(17) 0.0209(7) Uani 1 1 d . . . . .
C9 C 0.7204(4) 0.3137(3) 0.89212(17) 0.0258(8) Uani 1 1 d . . . . .
H9 H 0.741148 0.236312 0.889365 0.031 Uiso 1 1 calc R U . . .
C10 C 0.6468(4) 0.3705(3) 0.83107(17) 0.0239(7) Uani 1 1 d . . . . .
H10 H 0.618336 0.332547 0.786814 0.029 Uiso 1 1 calc R U . . .
C15 C 0.0722(4) 0.6137(3) 0.7467(2) 0.0303(8) Uani 1 1 d . . . . .
H15A H 0.069961 0.637070 0.696957 0.045 Uiso 1 1 calc R U . . .
H15B H 0.143999 0.666416 0.778661 0.045 Uiso 1 1 calc R U . . .
H15C H -0.051496 0.611619 0.757641 0.045 Uiso 1 1 calc R U . . .
C8 C 0.7641(5) 0.3668(3) 0.95664(18) 0.0269(8) Uani 1 1 d . . . . .
C6 C 0.6606(5) 0.5394(3) 0.89920(18) 0.0266(8) Uani 1 1 d . . . . .
H6 H 0.639893 0.616751 0.901930 0.032 Uiso 1 1 calc R U . . .
C12 C 0.2886(5) 0.4489(3) 0.59754(18) 0.0275(8) Uani 1 1 d . . . . .
C7 C 0.7367(5) 0.4809(3) 0.95905(18) 0.0314(8) Uani 1 1 d . . . . .
H7 H 0.771038 0.519221 1.002851 0.038 Uiso 1 1 calc R U . . .
C2 C 0.1781(4) 0.3295(3) 0.69210(19) 0.0270(8) Uani 1 1 d . . . . .
H2A H 0.124222 0.284943 0.650312 0.032 Uiso 1 1 calc R U . . .
H2B H 0.225452 0.278907 0.731729 0.032 Uiso 1 1 calc R U . . .
C16 C 0.1846(5) 0.4690(3) 0.83628(19) 0.0333(9) Uani 1 1 d . . . . .
H16A H 0.265524 0.523058 0.863334 0.050 Uiso 1 1 calc R U . . .
H16B H 0.238746 0.395082 0.842372 0.050 Uiso 1 1 calc R U . . .
H16C H 0.068207 0.468986 0.853931 0.050 Uiso 1 1 calc R U . . .
C3 C 0.0406(4) 0.4088(3) 0.7146(2) 0.0311(9) Uani 1 1 d . . . . .
H3 H -0.034472 0.369881 0.746309 0.037 Uiso 1 1 calc R U . . .
C11 C 0.8367(6) 0.3030(3) 1.02339(19) 0.0409(10) Uani 1 1 d . . . . .
H11A H 0.864277 0.226961 1.010523 0.061 Uiso 1 1 calc R U . . .
H11B H 0.746101 0.301841 1.055627 0.061 Uiso 1 1 calc R U . . .
H11C H 0.947091 0.338768 1.047375 0.061 Uiso 1 1 calc R U . . .
C14 C 0.2628(6) 0.2906(3) 0.43581(19) 0.0419(10) Uani 1 1 d . . . . .
H14A H 0.167006 0.240016 0.445393 0.063 Uiso 1 1 calc R U . . .
H14B H 0.380757 0.255614 0.450315 0.063 Uiso 1 1 calc R U . . .
H14C H 0.247101 0.307585 0.384593 0.063 Uiso 1 1 calc R U . . .
C13 C 0.2528(6) 0.3945(3) 0.47686(19) 0.0439(10) Uani 1 1 d . . . . .
H13A H 0.343921 0.448226 0.465320 0.053 Uiso 1 1 calc R U . . .
H13B H 0.131544 0.428274 0.464950 0.053 Uiso 1 1 calc R U . . .
O5 O -0.0666(4) 0.4440(2) 0.65341(14) 0.0433(7) Uani 1 1 d . . . . .
H5 H -0.158597 0.475739 0.664119 0.065 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 1.430(2) . ?
S1 O2 1.432(2) . ?
S1 N1 1.607(3) . ?
S1 C5 1.766(3) . ?
O3 C12 1.197(4) . ?
O4 C12 1.326(4) . ?
O4 C13 1.454(4) . ?
N1 C1 1.471(4) . ?
N1 C4 1.505(4) . ?
C5 C10 1.383(4) . ?
C5 C6 1.389(4) . ?
C1 H1 1.0000 . ?
C1 C12 1.512(5) . ?
C1 C2 1.518(4) . ?
C4 C15 1.508(4) . ?
C4 C16 1.527(5) . ?
C4 C3 1.545(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(4) . ?
C9 C8 1.374(5) . ?
C10 H10 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C8 C7 1.394(5) . ?
C8 C11 1.508(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.381(5) . ?
C7 H7 0.9500 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.514(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C3 H3 1.0000 . ?
C3 O5 1.372(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C14 C13 1.483(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
O5 H5 0.8400 . ?

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 119.08(14) . . ?
O1 S1 N1 108.87(13) . . ?
O1 S1 C5 106.67(14) . . ?
O2 S1 N1 105.58(13) . . ?
O2 S1 C5 107.57(14) . . ?
N1 S1 C5 108.76(14) . . ?
C12 O4 C13 115.5(3) . . ?
C1 N1 S1 120.7(2) . . ?
C1 N1 C4 112.8(2) . . ?
C4 N1 S1 125.0(2) . . ?
C10 C5 S1 119.7(2) . . ?
C10 C5 C6 120.4(3) . . ?
C6 C5 S1 119.9(2) . . ?
N1 C1 H1 110.1 . . ?
N1 C1 C12 111.2(2) . . ?
N1 C1 C2 101.7(2) . . ?
C12 C1 H1 110.1 . . ?
C12 C1 C2 113.5(3) . . ?
C2 C1 H1 110.1 . . ?
N1 C4 C15 111.0(3) . . ?
N1 C4 C16 111.7(3) . . ?
N1 C4 C3 101.6(2) . . ?
C15 C4 C16 110.2(3) . . ?
C15 C4 C3 113.3(3) . . ?
C16 C4 C3 108.7(3) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C8 C9 C10 121.4(3) . . ?
C5 C10 C9 119.5(3) . . ?
C5 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C4 C15 H15A 109.5 . . ?
C4 C15 H15B 109.5 . . ?
C4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C9 C8 C7 118.3(3) . . ?
C9 C8 C11 120.8(3) . . ?
C7 C8 C11 120.9(3) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 C5 118.8(3) . . ?
C7 C6 H6 120.6 . . ?
O3 C12 O4 124.2(3) . . ?
O3 C12 C1 127.1(3) . . ?
O4 C12 C1 108.7(3) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 C8 121.5(3) . . ?
C6 C7 H7 119.3 . . ?
C1 C2 H2A 110.9 . . ?
C1 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
C3 C2 C1 104.3(3) . . ?
C3 C2 H2A 110.9 . . ?
C3 C2 H2B 110.9 . . ?
C4 C16 H16A 109.5 . . ?
C4 C16 H16B 109.5 . . ?
C4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C4 C3 H3 110.0 . . ?
C2 C3 C4 104.4(3) . . ?
C2 C3 H3 110.0 . . ?
O5 C3 C4 115.2(3) . . ?
O5 C3 C2 107.1(3) . . ?
O5 C3 H3 110.0 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
O4 C13 C14 106.9(3) . . ?
O4 C13 H13A 110.3 . . ?
O4 C13 H13B 110.3 . . ?
C14 C13 H13A 110.3 . . ?
C14 C13 H13B 110.3 . . ?
H13A C13 H13B 108.6 . . ?
C3 O5 H5 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 C1 C12 -92.4(3) . . . . ?
S1 N1 C1 C2 146.5(2) . . . . ?
S1 N1 C4 C15 70.1(3) . . . . ?
S1 N1 C4 C16 -53.4(3) . . . . ?
S1 N1 C4 C3 -169.1(2) . . . . ?
S1 C5 C10 C9 -177.7(2) . . . . ?
S1 C5 C6 C7 178.8(3) . . . . ?
O1 S1 N1 C1 154.5(2) . . . . ?
O1 S1 N1 C4 -40.4(3) . . . . ?
O1 S1 C5 C10 171.0(2) . . . . ?
O1 S1 C5 C6 -8.3(3) . . . . ?
O2 S1 N1 C1 25.6(3) . . . . ?
O2 S1 N1 C4 -169.4(2) . . . . ?
O2 S1 C5 C10 -60.1(3) . . . . ?
O2 S1 C5 C6 120.5(3) . . . . ?
N1 S1 C5 C10 53.8(3) . . . . ?
N1 S1 C5 C6 -125.6(3) . . . . ?
N1 C1 C12 O3 0.7(5) . . . . ?
N1 C1 C12 O4 -179.9(3) . . . . ?
N1 C1 C2 C3 35.7(3) . . . . ?
N1 C4 C3 C2 25.4(3) . . . . ?
N1 C4 C3 O5 -91.7(3) . . . . ?
C5 S1 N1 C1 -89.6(2) . . . . ?
C5 S1 N1 C4 75.4(3) . . . . ?
C5 C6 C7 C8 -1.6(5) . . . . ?
C1 N1 C4 C15 -123.9(3) . . . . ?
C1 N1 C4 C16 112.6(3) . . . . ?
C1 N1 C4 C3 -3.1(3) . . . . ?
C1 C2 C3 C4 -38.9(3) . . . . ?
C1 C2 C3 O5 83.7(3) . . . . ?
C4 N1 C1 C12 100.9(3) . . . . ?
C4 N1 C1 C2 -20.2(3) . . . . ?
C9 C8 C7 C6 2.7(5) . . . . ?
C10 C5 C6 C7 -0.6(5) . . . . ?
C10 C9 C8 C7 -1.6(5) . . . . ?
C10 C9 C8 C11 177.4(3) . . . . ?
C15 C4 C3 C2 144.6(3) . . . . ?
C15 C4 C3 O5 27.5(4) . . . . ?
C8 C9 C10 C5 -0.5(5) . . . . ?
C6 C5 C10 C9 1.6(5) . . . . ?
C12 O4 C13 C14 178.7(3) . . . . ?
C12 C1 C2 C3 -83.8(3) . . . . ?
C2 C1 C12 O3 114.6(4) . . . . ?
C2 C1 C12 O4 -65.9(4) . . . . ?
C16 C4 C3 C2 -92.5(3) . . . . ?
C16 C4 C3 O5 150.4(3) . . . . ?
C11 C8 C7 C6 -176.3(3) . . . . ?
C13 O4 C12 O3 -0.7(5) . . . . ?
C13 O4 C12 C1 179.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# 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_rvo_04112024_needle_autored
_database_code_depnum_ccdc_archive 'CCDC 2385173'
loop_
_audit_author_name
_audit_author_address
'Gonzalo Campillo-Alvarado'
;Reed College
United States of America
;
_audit_update_record             
;
2024-09-19 deposited with the CCDC.	2025-01-27 downloaded from the CCDC.
;
_audit_creation_date             2024-04-12
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H19 N O5 S'
_chemical_formula_sum            'C14 H19 N O5 S'
_chemical_formula_weight         313.36
_chemical_absolute_configuration .
_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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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'

_cell_length_a                   11.4970(17)
_cell_length_b                   20.881(3)
_cell_length_c                   6.4271(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1543.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1767
_cell_measurement_temperature    99.97(16)
_cell_measurement_theta_max      20.9200
_cell_measurement_theta_min      2.0200
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.805
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.118a (Rigaku Oxford Diffraction, 2024)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.0373
0 -1 0 0.0233
0 1 0 0.0093
-1 1 0 0.0318
1 -1 0 0.0165
0 2 -1 0.3523
0 -1 2 0.5589
2 1 0 0.0132
-2 -1 0 0.0384
1 2 0 0.0069
-1 -2 0 0.0354
2 0 -1 0.2527

_exptl_crystal_size_max          0.988
_exptl_crystal_size_mid          0.053
_exptl_crystal_size_min          0.033
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.9989 -0.0093 0.0007 0.0260 0.0307 0.0467
0.0020 -0.9998 -0.0001 -0.0248 0.0231 -0.0014
-0.0020 0.9998 0.0001 0.0248 -0.0231 0.0014
-1.0009 0.9905 0.0008 0.0508 0.0075 0.0481
1.0009 -0.9905 -0.0008 -0.0508 -0.0075 -0.0481
-0.0054 2.0020 -0.9985 0.1088 0.0127 -0.0691
0.0049 -1.0045 1.9974 -0.1432 -0.0948 0.1424
1.9958 1.0184 -0.0013 -0.0272 -0.0845 -0.0920
-1.9958 -1.0184 0.0013 0.0272 0.0845 0.0920
0.9950 2.0089 -0.0005 0.0236 -0.0770 -0.0439
-0.9950 -2.0089 0.0005 -0.0236 0.0770 0.0439
1.9963 0.0210 -1.0002 0.0072 -0.0023 -0.1653

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0928
_diffrn_reflns_av_unetI/netI     0.1095
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            10443
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.990
_diffrn_reflns_theta_max         24.990
_diffrn_reflns_theta_min         2.635
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(16)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  78.00   0.50   48.00    --   20.00  54.00  60.00  284
  2  ω    -59.00 -34.00   0.50   48.00    --   20.00  54.00 150.00   50
  3  ω    -11.00  15.00   0.50   48.00    --   20.00  54.00 150.00   52
  4  ω     84.00 109.00   0.50   48.00    --   20.00  54.00 150.00   50
  5  ω    -60.00 -16.00   0.50   48.00    --   20.00  54.00-150.00   88
  6  ω     20.00  45.00   0.50   48.00    --   20.00  54.00-150.00   50
  7  ω    -54.00  84.00   0.50   48.00    --   20.00  54.00 -90.00  276
  8  ω     37.00  62.00   0.50   48.00    --   20.00  54.00  30.00   50
  9  ω     -3.00 105.00   0.50   48.00    --   20.00  54.00 -60.00  216
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0263035000
_diffrn_orient_matrix_UB_12      0.0247845000
_diffrn_orient_matrix_UB_13      -0.0591654000
_diffrn_orient_matrix_UB_21      -0.0305165000
_diffrn_orient_matrix_UB_22      -0.0232045000
_diffrn_orient_matrix_UB_23      -0.0590484000
_diffrn_orient_matrix_UB_31      -0.0467027000
_diffrn_orient_matrix_UB_32      0.0012947000
_diffrn_orient_matrix_UB_33      0.0720600000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.818
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                1730
_reflns_number_total             2707
_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 1.171.43.118a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.118a 64-bit (release 27-03-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.118a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 551 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2707
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1056
_refine_ls_R_factor_gt           0.0577
_refine_ls_restrained_S_all      0.983
_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)+(0.0387P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1127
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3A), C1(H1A)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C12(H12), C13(H13), C9(H9), C10(H10)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C6(H6A,H6B,H6C), C14(H14A,H14B,H14C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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 0.33093(12) 0.49201(7) 0.7570(3) 0.0334(4) Uani 1 1 d . . . . .
O4 O 0.2516(4) 0.45884(19) 0.8931(6) 0.0414(12) Uani 1 1 d . . . . .
O3 O 0.1949(4) 0.27933(19) 0.4533(8) 0.0487(13) Uani 1 1 d . . . . .
H3 H 0.154533 0.246736 0.478780 0.073 Uiso 1 1 calc R U . . .
O5 O 0.4123(4) 0.53785(18) 0.8427(7) 0.0427(12) Uani 1 1 d . . . . .
O2 O 0.4263(4) 0.30130(19) 0.3273(8) 0.0518(14) Uani 1 1 d . . . . .
O1 O 0.5249(4) 0.3146(2) 0.6238(8) 0.0588(15) Uani 1 1 d . . . . .
N1 N 0.4106(4) 0.4386(2) 0.6410(8) 0.0334(13) Uani 1 1 d . . . . .
H1 H 0.486703 0.443111 0.636979 0.040 Uiso 1 1 calc R U . . .
C8 C 0.2480(5) 0.5320(3) 0.5661(10) 0.0292(14) Uani 1 1 d . . . . .
C12 C 0.0631(6) 0.5637(3) 0.4292(11) 0.0400(17) Uani 1 1 d . . . . .
H12 H -0.019371 0.563834 0.438882 0.048 Uiso 1 1 calc R U . . .
C5 C 0.2241(6) 0.2806(3) 0.2351(13) 0.0417(17) Uani 1 1 d . . . . .
C11 C 0.1152(5) 0.5950(3) 0.2678(13) 0.0391(16) Uani 1 1 d . . . . .
C13 C 0.1272(5) 0.5316(3) 0.5793(11) 0.0330(15) Uani 1 1 d . . . . .
H13 H 0.089200 0.509720 0.689580 0.040 Uiso 1 1 calc R U . . .
C9 C 0.3034(6) 0.5648(3) 0.4056(11) 0.0389(17) Uani 1 1 d . . . . .
H9 H 0.385924 0.566266 0.399042 0.047 Uiso 1 1 calc R U . . .
C2 C 0.3071(5) 0.3921(3) 0.3274(10) 0.0371(17) Uani 1 1 d . . . . .
H2A H 0.349225 0.426422 0.252438 0.044 Uiso 1 1 calc R U . . .
H2B H 0.223453 0.403278 0.333128 0.044 Uiso 1 1 calc R U . . .
C3 C 0.3557(5) 0.3833(3) 0.5433(10) 0.0323(16) Uani 1 1 d . . . . .
H3A H 0.292816 0.366919 0.636664 0.039 Uiso 1 1 calc R U . . .
C10 C 0.2367(5) 0.5953(3) 0.2551(12) 0.0379(15) Uani 1 1 d . . . . .
H10 H 0.273905 0.616514 0.142608 0.046 Uiso 1 1 calc R U . . .
C1 C 0.3248(5) 0.3276(3) 0.2206(11) 0.0418(18) Uani 1 1 d . . . . .
H1A H 0.344421 0.334903 0.070846 0.050 Uiso 1 1 calc R U . . .
C7 C 0.1214(6) 0.3052(3) 0.1099(12) 0.057(2) Uani 1 1 d . . . . .
H7A H 0.056066 0.275323 0.123618 0.085 Uiso 1 1 calc R U . . .
H7B H 0.143499 0.308743 -0.036844 0.085 Uiso 1 1 calc R U . . .
H7C H 0.098183 0.347393 0.162305 0.085 Uiso 1 1 calc R U . . .
C4 C 0.4464(6) 0.3303(3) 0.5111(13) 0.0463(19) Uani 1 1 d . . . . .
C6 C 0.2594(7) 0.2145(3) 0.1581(14) 0.072(3) Uani 1 1 d . . . . .
H6A H 0.320413 0.197128 0.248505 0.108 Uiso 1 1 calc R U . . .
H6B H 0.288803 0.217702 0.015408 0.108 Uiso 1 1 calc R U . . .
H6C H 0.191689 0.185965 0.160971 0.108 Uiso 1 1 calc R U . . .
C14 C 0.0439(6) 0.6300(3) 0.1028(12) 0.062(2) Uani 1 1 d . . . . .
H14A H -0.038940 0.621198 0.124614 0.092 Uiso 1 1 calc R U . . .
H14B H 0.066969 0.615011 -0.035707 0.092 Uiso 1 1 calc R U . . .
H14C H 0.057877 0.676156 0.113527 0.092 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 O4 1.441(4) . ?
S1 O5 1.447(4) . ?
S1 N1 1.624(5) . ?
S1 C8 1.764(6) . ?
O3 C5 1.442(8) . ?
O2 C1 1.461(7) . ?
O2 C4 1.348(8) . ?
O1 C4 1.202(7) . ?
N1 C3 1.459(7) . ?
C8 C13 1.391(7) . ?
C8 C9 1.393(8) . ?
C12 C11 1.365(9) . ?
C12 C13 1.387(9) . ?
C5 C1 1.520(8) . ?
C5 C7 1.519(8) . ?
C5 C6 1.523(8) . ?
C11 C10 1.399(7) . ?
C11 C14 1.526(9) . ?
C9 C10 1.389(9) . ?
C2 C3 1.508(8) . ?
C2 C1 1.525(8) . ?
C3 C4 1.534(8) . ?

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
O4 S1 O5 119.8(3) . . ?
O4 S1 N1 107.8(2) . . ?
O4 S1 C8 107.9(3) . . ?
O5 S1 N1 105.3(2) . . ?
O5 S1 C8 107.5(3) . . ?
N1 S1 C8 108.1(3) . . ?
C4 O2 C1 112.3(5) . . ?
C3 N1 S1 119.8(4) . . ?
C13 C8 S1 119.6(5) . . ?
C13 C8 C9 120.3(6) . . ?
C9 C8 S1 120.0(5) . . ?
C11 C12 C13 121.8(6) . . ?
O3 C5 C1 104.4(6) . . ?
O3 C5 C7 109.9(5) . . ?
O3 C5 C6 111.1(6) . . ?
C1 C5 C6 111.3(5) . . ?
C7 C5 C1 110.0(5) . . ?
C7 C5 C6 110.0(6) . . ?
C12 C11 C10 119.0(7) . . ?
C12 C11 C14 121.4(6) . . ?
C10 C11 C14 119.6(7) . . ?
C12 C13 C8 119.1(6) . . ?
C10 C9 C8 119.2(6) . . ?
C3 C2 C1 104.9(5) . . ?
N1 C3 C2 117.4(5) . . ?
N1 C3 C4 109.6(5) . . ?
C2 C3 C4 102.5(5) . . ?
C9 C10 C11 120.6(7) . . ?
O2 C1 C5 109.7(5) . . ?
O2 C1 C2 103.2(5) . . ?
C5 C1 C2 116.1(5) . . ?
O2 C4 C3 109.0(6) . . ?
O1 C4 O2 122.3(7) . . ?
O1 C4 C3 128.7(7) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.008
_oxdiff_exptl_absorpt_empirical_full_min 0.545
####################################################################### 
# 
# 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_rvo_21fb2_trans_diol_041924_autored
_database_code_depnum_ccdc_archive 'CCDC 2386128'
loop_
_audit_author_name
_audit_author_address
'Gonzalo Campillo-Alvarado'
;Reed College
United States of America
;
_audit_update_record             
;
2024-09-24 deposited with the CCDC.	2025-01-27 downloaded from the CCDC.
;
_audit_creation_date             2024-08-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H23 N O5 S'
_chemical_formula_sum            'C16 H23 N O5 S'
_chemical_formula_weight         341.41
_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   20.066(2)
_cell_length_b                   5.1482(5)
_cell_length_c                   18.0857(18)
_cell_angle_alpha                90
_cell_angle_beta                 110.174(12)
_cell_angle_gamma                90
_cell_volume                     1753.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2159
_cell_measurement_temperature    99.8(9)
_cell_measurement_theta_max      29.3090
_cell_measurement_theta_min      2.5760
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.883
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.773
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.119a (Rigaku Oxford Diffraction, 2024)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             728
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 2 -2 0.1962
-1 0 -2 0.0207
1 0 2 0.0207
-2 1 -2 0.1567
0 1 1 0.1936
2 0 1 0.0177
1 -2 1 0.3927
-1 0 1 0.0217
1 0 -1 0.0186
-2 1 1 0.1750
1 0 0 0.0128
-1 0 0 0.0207

_exptl_crystal_size_max          0.614
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.033
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1116
_diffrn_reflns_av_unetI/netI     0.1082
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11944
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.266
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     80.00 108.00   0.50   50.00    --   20.00  54.00  60.00   56
  2  ω    -69.00  54.00   0.50   50.00    --   20.00  54.00 -30.00  246
  3  ω     63.00  97.00   0.50   50.00    --   20.00  54.00 -30.00   68
  4  ω    -63.00  28.00   0.50   50.00    --   20.00  54.00  30.00  182
  5  ω     82.00 109.00   0.50   50.00    --   20.00  54.00  30.00   54
  6  ω     -1.00  27.00   0.50   50.00    --   20.00  54.00 -60.00   56
  7  ω    -15.00  12.00   0.50   50.00    --   20.00  54.00 -90.00   54
  8  ω     84.00 109.00   0.50   50.00    --   20.00  54.00 -90.00   50
  9  ω    -73.00 -30.00   0.50   50.00    --   20.00  54.00-150.00   86
 10  ω    -16.00 110.00   0.50   50.00    --   20.00  54.00-150.00  252
 11  ω     22.00  67.00   0.50   50.00    --   20.00  54.00  60.00   90
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1910
_reflns_number_total             3064
_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 1.171.43.119a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.119a 64-bit (release 08-04-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.119a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3064
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1125
_refine_ls_R_factor_gt           0.0654
_refine_ls_restrained_S_all      0.965
_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)+(0.0792P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1521
_refine_ls_wR_factor_ref         0.1691
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C1(H1A), C7(H7)
1.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B)
1.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C11(H11), C14(H14), C15(H15), C12(H12)
1.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C4(H4A,H4B,H4C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_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 0.32385(5) 0.58469(19) 0.21341(5) 0.0332(3) Uani 1 1 d . . . . .
O1 O 0.27791(13) 0.1020(5) 0.36523(13) 0.0382(6) Uani 1 1 d . . . . .
O2 O 0.21208(12) 0.3768(5) 0.40865(13) 0.0403(7) Uani 1 1 d . . . . .
O4 O 0.30274(12) 0.8524(4) 0.21026(13) 0.0369(6) Uani 1 1 d . . . . .
O5 O 0.32957(12) 0.4612(5) 0.14457(12) 0.0388(7) Uani 1 1 d . . . . .
O3 O 0.11616(14) 0.2459(5) 0.23032(17) 0.0551(8) Uani 1 1 d . . . . .
N1 N 0.26662(13) 0.4175(5) 0.23859(15) 0.0309(7) Uani 1 1 d . . . . .
H1 H 0.249745 0.270126 0.214826 0.037 Uiso 1 1 calc R U . . .
C13 C 0.53800(18) 0.4990(8) 0.4079(2) 0.0386(9) Uani 1 1 d . . . . .
C10 C 0.40691(17) 0.5557(7) 0.28972(18) 0.0297(8) Uani 1 1 d . . . . .
C11 C 0.42793(19) 0.7330(7) 0.3507(2) 0.0365(9) Uani 1 1 d . . . . .
H11 H 0.397840 0.873465 0.352473 0.044 Uiso 1 1 calc R U . . .
C14 C 0.51539(19) 0.3212(7) 0.3465(2) 0.0367(9) Uani 1 1 d . . . . .
H14 H 0.545197 0.179449 0.344948 0.044 Uiso 1 1 calc R U . . .
C2 C 0.24621(18) 0.3029(7) 0.35995(19) 0.0319(9) Uani 1 1 d . . . . .
C15 C 0.45040(19) 0.3480(7) 0.2880(2) 0.0347(9) Uani 1 1 d . . . . .
H15 H 0.435283 0.224603 0.246457 0.042 Uiso 1 1 calc R U . . .
C1 C 0.24335(17) 0.5181(7) 0.30245(18) 0.0306(8) Uani 1 1 d . . . . .
H1A H 0.278857 0.651882 0.331546 0.037 Uiso 1 1 calc R U . . .
C12 C 0.4935(2) 0.7027(8) 0.4091(2) 0.0429(10) Uani 1 1 d . . . . .
H12 H 0.508340 0.824772 0.451034 0.052 Uiso 1 1 calc R U . . .
C3 C 0.2143(2) 0.1959(8) 0.4712(2) 0.0444(10) Uani 1 1 d . . . . .
H3A H 0.263750 0.142444 0.500563 0.053 Uiso 1 1 calc R U . . .
H3B H 0.185911 0.038802 0.449138 0.053 Uiso 1 1 calc R U . . .
C6 C 0.11190(18) 0.4808(9) 0.2220(2) 0.0380(9) Uani 1 1 d . . . . .
C7 C 0.04710(19) 0.6109(8) 0.1645(2) 0.0433(10) Uani 1 1 d . . . . .
H7 H 0.036961 0.770727 0.190234 0.052 Uiso 1 1 calc R U . . .
C5 C 0.17201(18) 0.6560(7) 0.2680(2) 0.0361(9) Uani 1 1 d . . . . .
H5A H 0.159986 0.736254 0.311569 0.043 Uiso 1 1 calc R U . . .
H5B H 0.176658 0.797584 0.233075 0.043 Uiso 1 1 calc R U . . .
C16 C 0.61166(19) 0.4726(9) 0.4707(2) 0.0568(12) Uani 1 1 d . . . . .
H16A H 0.647953 0.512082 0.447471 0.085 Uiso 1 1 calc R U . . .
H16B H 0.618206 0.294598 0.491201 0.085 Uiso 1 1 calc R U . . .
H16C H 0.616032 0.594193 0.513859 0.085 Uiso 1 1 calc R U . . .
C4 C 0.1833(2) 0.3383(9) 0.5249(2) 0.0587(13) Uani 1 1 d . . . . .
H4A H 0.183517 0.223867 0.568247 0.088 Uiso 1 1 calc R U . . .
H4B H 0.134426 0.390295 0.494950 0.088 Uiso 1 1 calc R U . . .
H4C H 0.211884 0.493096 0.546181 0.088 Uiso 1 1 calc R U . . .
C8 C 0.0636(2) 0.6946(9) 0.0913(2) 0.0690(14) Uani 1 1 d . . . . .
H8A H 0.069282 0.540268 0.062385 0.104 Uiso 1 1 calc R U . . .
H8B H 0.107538 0.796372 0.107484 0.104 Uiso 1 1 calc R U . . .
H8C H 0.024421 0.800785 0.057371 0.104 Uiso 1 1 calc R U . . .
C9 C -0.0183(2) 0.4383(11) 0.1421(3) 0.0783(16) Uani 1 1 d . . . . .
H9A H -0.028746 0.392564 0.189586 0.117 Uiso 1 1 calc R U . . .
H9B H -0.009472 0.279708 0.116994 0.117 Uiso 1 1 calc R U . . .
H9C H -0.058835 0.531426 0.105372 0.117 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 O4 1.437(2) . ?
S1 O5 1.438(2) . ?
S1 N1 1.621(3) . ?
S1 C10 1.766(3) . ?
O1 C2 1.201(4) . ?
O2 C2 1.344(4) . ?
O2 C3 1.455(4) . ?
O3 C6 1.218(4) . ?
N1 H1 0.8800 . ?
N1 C1 1.481(4) . ?
C13 C14 1.389(5) . ?
C13 C12 1.382(5) . ?
C13 C16 1.528(5) . ?
C10 C11 1.380(4) . ?
C10 C15 1.387(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.374(5) . ?
C2 C1 1.507(5) . ?
C15 H15 0.9500 . ?
C1 H1A 1.0000 . ?
C1 C5 1.525(4) . ?
C12 H12 0.9500 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.510(5) . ?
C6 C7 1.513(5) . ?
C6 C5 1.507(5) . ?
C7 H7 1.0000 . ?
C7 C8 1.532(5) . ?
C7 C9 1.519(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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
O4 S1 O5 120.03(15) . . ?
O4 S1 N1 107.02(15) . . ?
O4 S1 C10 107.33(16) . . ?
O5 S1 N1 106.52(14) . . ?
O5 S1 C10 107.68(15) . . ?
N1 S1 C10 107.74(15) . . ?
C2 O2 C3 116.3(3) . . ?
S1 N1 H1 120.7 . . ?
C1 N1 S1 118.5(2) . . ?
C1 N1 H1 120.7 . . ?
C14 C13 C16 120.1(4) . . ?
C12 C13 C14 118.6(3) . . ?
C12 C13 C16 121.3(4) . . ?
C11 C10 S1 121.0(3) . . ?
C11 C10 C15 120.4(3) . . ?
C15 C10 S1 118.6(3) . . ?
C10 C11 H11 120.5 . . ?
C10 C11 C12 118.9(3) . . ?
C12 C11 H11 120.5 . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.7(3) . . ?
C15 C14 H14 119.6 . . ?
O1 C2 O2 124.6(3) . . ?
O1 C2 C1 125.5(3) . . ?
O2 C2 C1 109.7(3) . . ?
C10 C15 H15 120.1 . . ?
C14 C15 C10 119.8(3) . . ?
C14 C15 H15 120.1 . . ?
N1 C1 C2 109.5(3) . . ?
N1 C1 H1A 107.0 . . ?
N1 C1 C5 110.4(3) . . ?
C2 C1 H1A 107.0 . . ?
C2 C1 C5 115.5(3) . . ?
C5 C1 H1A 107.0 . . ?
C13 C12 C11 121.5(4) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
O2 C3 H3A 110.5 . . ?
O2 C3 H3B 110.5 . . ?
O2 C3 C4 106.3(3) . . ?
H3A C3 H3B 108.7 . . ?
C4 C3 H3A 110.5 . . ?
C4 C3 H3B 110.5 . . ?
O3 C6 C7 122.1(4) . . ?
O3 C6 C5 121.2(3) . . ?
C5 C6 C7 116.7(3) . . ?
C6 C7 H7 108.0 . . ?
C6 C7 C8 109.1(3) . . ?
C6 C7 C9 112.5(3) . . ?
C8 C7 H7 108.0 . . ?
C9 C7 H7 108.0 . . ?
C9 C7 C8 111.0(3) . . ?
C1 C5 H5A 108.8 . . ?
C1 C5 H5B 108.8 . . ?
C6 C5 C1 114.0(3) . . ?
C6 C5 H5A 108.8 . . ?
C6 C5 H5B 108.8 . . ?
H5A C5 H5B 107.6 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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 C1 C2 -132.8(3) . . . . ?
S1 N1 C1 C5 98.9(3) . . . . ?
S1 C10 C11 C12 -179.9(3) . . . . ?
S1 C10 C15 C14 179.8(3) . . . . ?
O1 C2 C1 N1 16.8(5) . . . . ?
O1 C2 C1 C5 142.2(4) . . . . ?
O2 C2 C1 N1 -167.6(3) . . . . ?
O2 C2 C1 C5 -42.3(4) . . . . ?
O4 S1 N1 C1 -43.2(3) . . . . ?
O4 S1 C10 C11 23.5(3) . . . . ?
O4 S1 C10 C15 -157.6(3) . . . . ?
O5 S1 N1 C1 -172.7(2) . . . . ?
O5 S1 C10 C11 154.0(3) . . . . ?
O5 S1 C10 C15 -27.1(3) . . . . ?
O3 C6 C7 C8 -103.4(4) . . . . ?
O3 C6 C7 C9 20.2(5) . . . . ?
O3 C6 C5 C1 19.0(5) . . . . ?
N1 S1 C10 C11 -91.5(3) . . . . ?
N1 S1 C10 C15 87.5(3) . . . . ?
N1 C1 C5 C6 64.0(4) . . . . ?
C13 C14 C15 C10 0.4(5) . . . . ?
C10 S1 N1 C1 72.0(3) . . . . ?
C10 C11 C12 C13 -0.3(5) . . . . ?
C11 C10 C15 C14 -1.2(5) . . . . ?
C14 C13 C12 C11 -0.4(5) . . . . ?
C2 O2 C3 C4 171.0(3) . . . . ?
C2 C1 C5 C6 -60.9(4) . . . . ?
C15 C10 C11 C12 1.2(5) . . . . ?
C12 C13 C14 C15 0.4(5) . . . . ?
C3 O2 C2 O1 -0.4(5) . . . . ?
C3 O2 C2 C1 -176.0(3) . . . . ?
C7 C6 C5 C1 -160.1(3) . . . . ?
C5 C6 C7 C8 75.7(4) . . . . ?
C5 C6 C7 C9 -160.6(3) . . . . ?
C16 C13 C14 C15 -177.6(3) . . . . ?
C16 C13 C12 C11 177.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# 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_rvo_04082024_autored
_database_code_depnum_ccdc_archive 'CCDC 2385172'
loop_
_audit_author_name
_audit_author_address
'Gonzalo Campillo-Alvarado'
;Reed College
United States of America
;
_audit_update_record             
;
2024-09-19 deposited with the CCDC.	2025-01-27 downloaded from the CCDC.
;
_audit_creation_date             2024-05-08
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H19 N O5 S'
_chemical_formula_sum            'C14 H19 N O5 S'
_chemical_formula_weight         313.36
_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   11.5944(8)
_cell_length_b                   11.4209(7)
_cell_length_c                   11.4442(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.045(5)
_cell_angle_gamma                90
_cell_volume                     1482.06(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2657
_cell_measurement_temperature    99.97(17)
_cell_measurement_theta_max      28.9820
_cell_measurement_theta_min      2.5270
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.936
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.849
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.118a (Rigaku Oxford Diffraction, 2024)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 14 8 0.0945
3 -12 10 0.0598
15 4 1 0.0324
-16 -5 2 0.0312
-14 9 0 0.0472
0 0 -1 0.1451
0 -1 -2 0.1437
0 2 1 0.0866
0 2 -1 0.0680
1 2 1 0.0741
1 2 -1 0.0654
2 2 1 0.0593
2 2 -1 0.0608
2 1 1 0.0500
1 1 -1 0.0809
2 1 0 0.0408
-1 0 -1 0.0877
2 1 -1 0.0647
1 0 0 0.0226
-2 1 -2 0.0744
2 -1 0 0.0472
2 -2 1 0.0493
-1 2 -2 0.0804
0 -1 0 0.1103
-2 -2 1 0.0559
-1 -2 2 0.0671
-2 -1 -1 0.0827

_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2.9762 13.9531 7.9871 0.4918 -0.8518 -0.1803
3.2167 -11.6996 9.7466 -0.2592 0.4489 -0.8552
15.2939 3.6349 1.0291 0.8750 0.3896 -0.2873
-15.5428 -4.6865 1.8537 -0.9090 -0.4047 0.0995
-13.5892 8.5722 0.2308 -0.2840 -0.8742 0.3939
0.0016 -0.0001 -1.0011 -0.0072 0.0178 0.0604
0.0029 -0.9998 -2.0025 -0.0555 0.0787 0.1032
-0.0012 1.9991 1.0018 0.0894 -0.1038 -0.0253
0.0019 1.9988 -1.0003 0.0750 -0.0681 0.0955
0.9984 1.9984 1.0019 0.1363 -0.0669 -0.0442
1.0015 1.9982 -1.0002 0.1219 -0.0312 0.0766
1.9979 1.9978 1.0020 0.1832 -0.0300 -0.0631
2.0011 1.9975 -1.0001 0.1688 0.0057 0.0577
1.9978 0.9983 1.0017 0.1421 0.0130 -0.0807
1.0013 0.9987 -1.0006 0.0808 0.0117 0.0591
1.9993 0.9981 0.0006 0.1349 0.0308 -0.0203
-0.9980 0.0005 -1.0012 -0.0541 -0.0191 0.0793
2.0009 0.9980 -1.0004 0.1277 0.0487 0.0401
0.9996 -0.0007 0.0001 0.0469 0.0369 -0.0189
-1.9958 1.0006 -2.0020 -0.0671 -0.0811 0.1762
1.9989 -1.0009 -0.0001 0.0527 0.1168 -0.0554
1.9972 -2.0002 1.0006 0.0188 0.1420 -0.1334
-0.9961 1.9994 -2.0015 0.0209 -0.0872 0.1749
-0.0002 -0.9995 -0.0004 -0.0411 0.0430 -0.0176
-2.0011 -1.9975 1.0001 -0.1688 -0.0057 -0.0577
-1.0031 -1.9980 2.0013 -0.1147 0.0134 -0.1370
-1.9978 -0.9983 -1.0017 -0.1421 -0.0130 0.0807

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0786
_diffrn_reflns_av_unetI/netI     0.0819
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12516
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.531
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(17)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -18.00 107.00   0.50   40.00    --   20.00  54.00  90.00  250
  2  ω    -53.00   7.00   0.50   40.00    --   20.00  54.00-150.00  120
  3  ω     44.00  71.00   0.50   40.00    --   20.00  54.00-150.00   54
  4  ω    -73.00 -41.00   0.50   40.00    --   20.00  54.00 120.00   64
  5  ω     22.00  47.00   0.50   40.00    --   20.00  54.00 120.00   50
  6  ω     85.00 110.00   0.50   40.00    --   20.00  54.00 120.00   50
  7  ω    -71.00 109.00   0.50   40.00    --   20.00  54.00 -90.00  360
  8  ω    -12.00  13.00   0.50   40.00    --   20.00  54.00  60.00   50
  9  ω    -74.00 108.00   0.50   40.00    --   20.00  54.00-120.00  364
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0469552000
_diffrn_orient_matrix_UB_12      0.0411073000
_diffrn_orient_matrix_UB_13      0.0072587000
_diffrn_orient_matrix_UB_21      0.0368913000
_diffrn_orient_matrix_UB_22      -0.0430157000
_diffrn_orient_matrix_UB_23      -0.0177573000
_diffrn_orient_matrix_UB_31      -0.0189095000
_diffrn_orient_matrix_UB_32      0.0176018000
_diffrn_orient_matrix_UB_33      -0.0603734000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1685
_reflns_number_total             2607
_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 1.171.43.118a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.118a 64-bit (release 27-03-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.118a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2607
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0919
_refine_ls_R_factor_gt           0.0481
_refine_ls_restrained_S_all      0.985
_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)+(0.0476P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1114
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C3(H3A), C1(H1A)
1.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
1.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C9(H9), C13(H13), C10(H10), C12(H12)
1.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C14(H14A,H14B,H14C)
1.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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 0.74674(6) 0.67777(7) 0.51339(6) 0.0287(2) Uani 1 1 d . . . . .
O3 O 0.37622(17) 0.45103(16) 0.19131(16) 0.0302(5) Uani 1 1 d . . . . .
H3 H 0.349746 0.432274 0.251659 0.045 Uiso 1 1 calc R U . . .
O2 O 0.32956(16) 0.65812(16) 0.32360(16) 0.0307(5) Uani 1 1 d . . . . .
O4 O 0.82192(17) 0.77953(16) 0.53741(16) 0.0366(6) Uani 1 1 d . . . . .
O1 O 0.41749(17) 0.64297(18) 0.51627(16) 0.0376(6) Uani 1 1 d . . . . .
O5 O 0.71913(18) 0.61605(17) 0.61360(16) 0.0381(6) Uani 1 1 d . . . . .
N1 N 0.62807(19) 0.72403(19) 0.42642(19) 0.0271(6) Uani 1 1 d . . . . .
H1 H 0.617569 0.799982 0.416470 0.033 Uiso 1 1 calc R U . . .
C5 C 0.3130(2) 0.5528(2) 0.1347(2) 0.0260(7) Uani 1 1 d . . . . .
C11 C 0.9095(2) 0.4120(3) 0.2986(2) 0.0277(7) Uani 1 1 d . . . . .
C8 C 0.8092(2) 0.5748(2) 0.4302(2) 0.0247(7) Uani 1 1 d . . . . .
C9 C 0.8282(2) 0.6044(3) 0.3185(2) 0.0291(7) Uani 1 1 d . . . . .
H9 H 0.807204 0.680088 0.286773 0.035 Uiso 1 1 calc R U . . .
C13 C 0.8423(2) 0.4641(2) 0.4781(2) 0.0282(7) Uani 1 1 d . . . . .
H13 H 0.830273 0.443527 0.555074 0.034 Uiso 1 1 calc R U . . .
C10 C 0.8776(2) 0.5240(3) 0.2530(2) 0.0301(7) Uani 1 1 d . . . . .
H10 H 0.890069 0.544875 0.176196 0.036 Uiso 1 1 calc R U . . .
C3 C 0.5368(2) 0.6445(2) 0.3632(2) 0.0266(7) Uani 1 1 d . . . . .
H3A H 0.568267 0.562696 0.369730 0.032 Uiso 1 1 calc R U . . .
C1 C 0.3620(2) 0.6619(2) 0.2054(2) 0.0272(7) Uani 1 1 d . . . . .
H1A H 0.325326 0.732762 0.161397 0.033 Uiso 1 1 calc R U . . .
C4 C 0.4257(2) 0.6489(2) 0.4128(3) 0.0272(7) Uani 1 1 d . . . . .
C6 C 0.1814(2) 0.5388(3) 0.1293(3) 0.0345(8) Uani 1 1 d . . . . .
H6A H 0.152916 0.467749 0.084342 0.052 Uiso 1 1 calc R U . . .
H6B H 0.139269 0.606983 0.089498 0.052 Uiso 1 1 calc R U . . .
H6C H 0.167261 0.532500 0.210570 0.052 Uiso 1 1 calc R U . . .
C7 C 0.3379(3) 0.5592(3) 0.0089(2) 0.0351(8) Uani 1 1 d . . . . .
H7A H 0.423154 0.564672 0.014058 0.053 Uiso 1 1 calc R U . . .
H7B H 0.299105 0.628410 -0.032212 0.053 Uiso 1 1 calc R U . . .
H7C H 0.307400 0.488629 -0.035742 0.053 Uiso 1 1 calc R U . . .
C12 C 0.8928(2) 0.3848(3) 0.4120(3) 0.0296(7) Uani 1 1 d . . . . .
H12 H 0.916422 0.310113 0.445133 0.036 Uiso 1 1 calc R U . . .
C2 C 0.4960(2) 0.6761(3) 0.2315(2) 0.0330(7) Uani 1 1 d . . . . .
H2A H 0.531847 0.622919 0.180701 0.040 Uiso 1 1 calc R U . . .
H2B H 0.518023 0.757686 0.216728 0.040 Uiso 1 1 calc R U . . .
C14 C 0.9580(3) 0.3228(3) 0.2247(3) 0.0394(8) Uani 1 1 d . . . . .
H14A H 0.894372 0.270700 0.185665 0.059 Uiso 1 1 calc R U . . .
H14B H 1.019507 0.276737 0.276508 0.059 Uiso 1 1 calc R U . . .
H14C H 0.991638 0.362942 0.163888 0.059 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 O4 1.444(2) . ?
S1 O5 1.4380(19) . ?
S1 N1 1.610(2) . ?
S1 C8 1.762(3) . ?
O3 C5 1.452(3) . ?
O2 C1 1.479(3) . ?
O2 C4 1.349(3) . ?
O1 C4 1.210(3) . ?
N1 C3 1.466(3) . ?
C5 C1 1.529(4) . ?
C5 C6 1.522(4) . ?
C5 C7 1.528(4) . ?
C11 C10 1.402(4) . ?
C11 C12 1.387(4) . ?
C11 C14 1.505(4) . ?
C8 C9 1.382(3) . ?
C8 C13 1.400(4) . ?
C9 C10 1.384(4) . ?
C13 C12 1.385(4) . ?
C3 C4 1.514(4) . ?
C3 C2 1.525(3) . ?
C1 C2 1.528(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 S1 N1 104.93(11) . . ?
O4 S1 C8 109.88(13) . . ?
O5 S1 O4 117.94(12) . . ?
O5 S1 N1 110.50(12) . . ?
O5 S1 C8 106.80(13) . . ?
N1 S1 C8 106.25(12) . . ?
C4 O2 C1 111.5(2) . . ?
C3 N1 S1 122.52(18) . . ?
O3 C5 C1 108.6(2) . . ?
O3 C5 C6 110.0(2) . . ?
O3 C5 C7 106.3(2) . . ?
C6 C5 C1 111.5(2) . . ?
C6 C5 C7 110.6(2) . . ?
C7 C5 C1 109.6(2) . . ?
C10 C11 C14 120.5(3) . . ?
C12 C11 C10 118.4(3) . . ?
C12 C11 C14 121.1(3) . . ?
C9 C8 S1 119.9(2) . . ?
C9 C8 C13 120.0(3) . . ?
C13 C8 S1 120.1(2) . . ?
C8 C9 C10 120.2(3) . . ?
C12 C13 C8 119.3(3) . . ?
C9 C10 C11 120.7(3) . . ?
N1 C3 C4 112.2(2) . . ?
N1 C3 C2 112.6(2) . . ?
C4 C3 C2 104.5(2) . . ?
O2 C1 C5 108.8(2) . . ?
O2 C1 C2 105.5(2) . . ?
C2 C1 C5 116.2(2) . . ?
O2 C4 C3 110.6(2) . . ?
O1 C4 O2 121.6(3) . . ?
O1 C4 C3 127.8(3) . . ?
C13 C12 C11 121.5(3) . . ?
C3 C2 C1 105.2(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.166
_oxdiff_exptl_absorpt_empirical_full_min 0.893
