# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_hpd192c
_database_code_depnum_ccdc_archive 'CCDC 2042738'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman'
;University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2020-11-05 deposited with the CCDC.	2021-04-06 downloaded from the CCDC.
;
_audit_creation_date             2020-08-10
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H21 N O5 S'
_chemical_formula_sum            'C14 H21 N O5 S'
_chemical_formula_weight         315.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H S O N'
_chemical_oxdiff_usercomment     'VNY 206-2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   26.9877(4)
_cell_length_b                   5.72560(10)
_cell_length_c                   9.8987(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.078(2)
_cell_angle_gamma                90
_cell_volume                     1529.55(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8640
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.4470
_cell_measurement_theta_min      3.2630
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.075
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.563
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             672
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-7 -1 -6 0.0393
7 1 6 0.0861
-5 3 -1 0.1055
4 -4 1 0.0860
17 1 0 0.0494
-3 0 6 0.0643
-17 -1 1 0.0254
-4 -1 -6 0.0499

_exptl_crystal_size_max          0.204
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.079
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
-7.3564 -0.7264 -5.6913 0.0038 0.0083 1.0000
7.1707 0.8817 5.6576 -0.0140 -0.0505 -0.9986
-4.9967 3.4744 -1.3529 -0.2315 -0.9637 0.1329
4.1160 -3.5923 0.6520 0.2337 0.9723 -0.0089
17.0464 0.8484 -0.2262 0.8804 -0.2109 -0.4247
-3.0248 0.1956 6.3216 -0.5718 0.1390 -0.8085
-16.8727 -0.7936 1.0612 -0.9268 0.2223 0.3026
-3.6383 -0.5264 -6.2176 0.2267 -0.0563 0.9723

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14613
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.280
_diffrn_reflns_theta_min         3.275
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -42.00  27.00   0.50    0.05    --  -46.87  36.00-127.00  138
  2  ω    -80.00 -15.00   0.50    0.10    --  -88.50  89.00  59.00  130
  3  ω     34.00 108.00   0.50    0.10    --  106.69-112.00-140.00  148
  4  ω     92.00 178.00   0.50    0.10    --  106.69  36.00-127.00  172
  5  ω   -120.00 -87.00   0.50    0.05    --  -46.87-125.00 -60.00   66
  6  ω   -120.00 -87.00   0.50    0.05    --  -46.87-125.00-150.00   66
  7  ω   -120.00 -83.00   0.50    0.05    --  -46.87 -57.00 -60.00   74
  8  ω    -28.00  30.00   0.50    0.05    --   46.87 -19.00 -90.00  116
  9  ω    -51.00 -16.00   0.50    0.10    --  -88.50  45.00 -60.00   70
 10  ω    -51.00 -16.00   0.50    0.10    --  -88.50  45.00-150.00   70
 11  ω    -51.00 -16.00   0.50    0.10    --  -88.50  45.00 -90.00   70
 12  ω     34.00  71.00   0.50    0.10    --  106.69 -61.00 120.00   74
 13  ω     34.00 101.00   0.50    0.10    --  106.69 -77.00 -60.00  134
 14  ω     34.00  71.00   0.50    0.10    --  106.69 -61.00   0.00   74
 15  ω   -120.00 -83.00   0.50    0.05    --  -46.87 -57.00  90.00   74
 16  ω   -120.00 -83.00   0.50    0.05    --  -46.87 -57.00   0.00   74
 17  ω     32.00 121.00   0.50    0.05    --   46.87  37.00  90.00  178
 18  ω     32.00 121.00   0.50    0.05    --   46.87  37.00-150.00  178
 19  ω   -160.00-132.00   0.50    0.10    --  -88.50 -61.00 -30.00   56
 20  ω     83.00 108.00   0.50    0.05    --   46.87  57.00  30.00   50
 21  ω    -71.00 -15.00   0.50    0.10    --  -88.50  61.00 -60.00  112
 22  ω     68.00  98.00   0.50    0.10    --  106.69 -77.00  90.00   60
 23  ω     93.00 119.00   0.50    0.10    --  106.69  30.00   0.00   52
 24  ω    143.00 169.00   0.50    0.10    --  106.69  30.00   0.00   52
 25  ω     39.00  65.00   0.50    0.10    --  106.69 -77.00  90.00   52
 26  ω     37.00  66.00   0.50    0.10    --  106.69 -61.00  90.00   58
 27  ω    111.00 136.00   0.50    0.10    --  106.69  36.00-127.00   50
 28  ω   -120.00 -83.00   0.50    0.05    --  -46.87 -57.00 -30.00   74
 29  ω     32.00 121.00   0.50    0.05    --   46.87  37.00 150.00  178
 30  ω     32.00  61.00   0.50    0.05    --   46.87  37.00  30.00   58
 31  ω     32.00 121.00   0.50    0.05    --   46.87  37.00 -60.00  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0516639000
_diffrn_orient_matrix_UB_12      -0.0177053000
_diffrn_orient_matrix_UB_13      -0.0651874000
_diffrn_orient_matrix_UB_21      0.0011624000
_diffrn_orient_matrix_UB_22      -0.2637480000
_diffrn_orient_matrix_UB_23      0.0307031000
_diffrn_orient_matrix_UB_31      -0.0242425000
_diffrn_orient_matrix_UB_32      -0.0503246000
_diffrn_orient_matrix_UB_33      -0.1379405000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2713
_reflns_number_total             2942
_reflns_odcompleteness_completeness 96.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2942
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0326
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0439P)²+0.7163P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.0863
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C2(H2A,H2B), C6(H6A,H6B), C1(H1A,H1B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C8(H8)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C13(H13A,H13B,H13C)
;
_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 0.18029(2) 1.00656(5) 0.48132(3) 0.01663(11) Uani 1 1 d . . . . .
O5 O 0.44080(3) 0.70529(16) 0.26931(10) 0.0191(2) Uani 1 1 d . . . . .
O4 O 0.41593(3) 0.34277(16) 0.13410(10) 0.0187(2) Uani 1 1 d . . . . .
O2 O 0.17071(4) 0.89719(18) 0.60914(10) 0.0225(2) Uani 1 1 d . . . . .
O3 O 0.19901(4) 1.24125(17) 0.48009(11) 0.0233(2) Uani 1 1 d . . . . .
O1 O 0.04857(4) 0.9472(2) 0.21367(12) 0.0286(3) Uani 1 1 d . . . . .
N1 N 0.12763(4) 1.00963(19) 0.39781(12) 0.0175(3) Uani 1 1 d . . . . .
C9 C 0.33066(5) 0.3571(2) 0.21701(14) 0.0179(3) Uani 1 1 d . . . . .
H9 H 0.321578 0.223638 0.169513 0.021 Uiso 1 1 calc R U . . .
C10 C 0.37859(5) 0.4410(2) 0.20792(13) 0.0155(3) Uani 1 1 d . . . . .
C11 C 0.39216(5) 0.6429(2) 0.28118(14) 0.0156(3) Uani 1 1 d . . . . .
C7 C 0.30842(5) 0.6730(2) 0.36769(14) 0.0187(3) Uani 1 1 d . . . . .
C12 C 0.35711(5) 0.7570(2) 0.35876(14) 0.0168(3) Uani 1 1 d . . . . .
H12 H 0.365963 0.891378 0.405696 0.020 Uiso 1 1 calc R U . . .
C8 C 0.29588(5) 0.4722(2) 0.29730(15) 0.0197(3) Uani 1 1 d . . . . .
H8 H 0.263847 0.413348 0.303630 0.024 Uiso 1 1 calc R U . . .
C3 C 0.12920(5) 1.1176(3) 0.26198(15) 0.0219(3) Uani 1 1 d . . . . .
H3A H 0.146055 1.014867 0.199118 0.026 Uiso 1 1 calc R U . . .
H3B H 0.147068 1.264480 0.265593 0.026 Uiso 1 1 calc R U . . .
C14 C 0.45787(5) 0.8944(2) 0.35245(15) 0.0217(3) Uani 1 1 d . . . . .
H14A H 0.440725 1.035074 0.327891 0.033 Uiso 1 1 calc R U . . .
H14B H 0.492829 0.915637 0.339443 0.033 Uiso 1 1 calc R U . . .
H14C H 0.451486 0.858990 0.445605 0.033 Uiso 1 1 calc R U . . .
C5 C 0.22121(5) 0.8259(3) 0.38755(15) 0.0204(3) Uani 1 1 d . . . . .
H5A H 0.206517 0.672251 0.377326 0.024 Uiso 1 1 calc R U . . .
H5B H 0.225608 0.891589 0.298045 0.024 Uiso 1 1 calc R U . . .
C13 C 0.40305(5) 0.1461(2) 0.05221(14) 0.0205(3) Uani 1 1 d . . . . .
H13A H 0.377160 0.189462 -0.009489 0.031 Uiso 1 1 calc R U . . .
H13B H 0.391760 0.021000 0.108895 0.031 Uiso 1 1 calc R U . . .
H13C H 0.431591 0.095945 0.002229 0.031 Uiso 1 1 calc R U . . .
C2 C 0.09849(5) 0.7912(2) 0.39785(16) 0.0220(3) Uani 1 1 d . . . . .
H2A H 0.096536 0.728291 0.488680 0.026 Uiso 1 1 calc R U . . .
H2B H 0.114138 0.675805 0.340230 0.026 Uiso 1 1 calc R U . . .
C6 C 0.27158(5) 0.8017(3) 0.45547(15) 0.0237(3) Uani 1 1 d . . . . .
H6A H 0.284435 0.955925 0.475914 0.028 Uiso 1 1 calc R U . . .
H6B H 0.267683 0.718317 0.540090 0.028 Uiso 1 1 calc R U . . .
C1 C 0.04704(5) 0.8476(3) 0.34568(17) 0.0271(3) Uani 1 1 d . . . . .
H1A H 0.027397 0.705738 0.343414 0.032 Uiso 1 1 calc R U . . .
H1B H 0.031101 0.956139 0.407006 0.032 Uiso 1 1 calc R U . . .
C4 C 0.07632(6) 1.1590(3) 0.21580(17) 0.0283(3) Uani 1 1 d . . . . .
H4A H 0.060479 1.269309 0.276274 0.034 Uiso 1 1 calc R U . . .
H4B H 0.076568 1.226757 0.125994 0.034 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4356(10) . ?
S1 O3 1.4357(10) . ?
S1 N1 1.6431(12) . ?
S1 C5 1.7760(14) . ?
O5 C11 1.3655(16) . ?
O5 C14 1.4357(16) . ?
O4 C10 1.3668(16) . ?
O4 C13 1.4299(16) . ?
O1 C1 1.427(2) . ?
O1 C4 1.4252(19) . ?
N1 C3 1.4806(18) . ?
N1 C2 1.4775(17) . ?
C9 H9 0.9300 . ?
C9 C10 1.3828(19) . ?
C9 C8 1.396(2) . ?
C10 C11 1.4126(19) . ?
C11 C12 1.3832(19) . ?
C7 C12 1.4021(19) . ?
C7 C8 1.386(2) . ?
C7 C6 1.513(2) . ?
C12 H12 0.9300 . ?
C8 H8 0.9300 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.517(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.5221(19) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.515(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O3 118.66(6) . . ?
O2 S1 N1 106.94(6) . . ?
O2 S1 C5 108.63(7) . . ?
O3 S1 N1 106.85(6) . . ?
O3 S1 C5 108.77(7) . . ?
N1 S1 C5 106.34(6) . . ?
C11 O5 C14 117.12(10) . . ?
C10 O4 C13 116.64(10) . . ?
C4 O1 C1 110.03(12) . . ?
C3 N1 S1 115.82(9) . . ?
C2 N1 S1 116.80(9) . . ?
C2 N1 C3 111.69(11) . . ?
C10 C9 H9 119.9 . . ?
C10 C9 C8 120.18(13) . . ?
C8 C9 H9 119.9 . . ?
O4 C10 C9 125.60(12) . . ?
O4 C10 C11 114.86(12) . . ?
C9 C10 C11 119.53(12) . . ?
O5 C11 C10 114.74(12) . . ?
O5 C11 C12 125.63(12) . . ?
C12 C11 C10 119.62(12) . . ?
C12 C7 C6 119.06(12) . . ?
C8 C7 C12 118.76(13) . . ?
C8 C7 C6 122.18(13) . . ?
C11 C12 C7 120.98(13) . . ?
C11 C12 H12 119.5 . . ?
C7 C12 H12 119.5 . . ?
C9 C8 H8 119.5 . . ?
C7 C8 C9 120.91(13) . . ?
C7 C8 H8 119.5 . . ?
N1 C3 H3A 110.1 . . ?
N1 C3 H3B 110.1 . . ?
N1 C3 C4 108.11(12) . . ?
H3A C3 H3B 108.4 . . ?
C4 C3 H3A 110.1 . . ?
C4 C3 H3B 110.1 . . ?
O5 C14 H14A 109.5 . . ?
O5 C14 H14B 109.5 . . ?
O5 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
S1 C5 H5A 109.2 . . ?
S1 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 S1 112.19(10) . . ?
C6 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C2 H2A 110.1 . . ?
N1 C2 H2B 110.1 . . ?
N1 C2 C1 107.89(12) . . ?
H2A C2 H2B 108.4 . . ?
C1 C2 H2A 110.1 . . ?
C1 C2 H2B 110.1 . . ?
C7 C6 C5 112.20(12) . . ?
C7 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
O1 C1 C2 111.71(12) . . ?
O1 C1 H1A 109.3 . . ?
O1 C1 H1B 109.3 . . ?
C2 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
H1A C1 H1B 107.9 . . ?
O1 C4 C3 111.47(12) . . ?
O1 C4 H4A 109.3 . . ?
O1 C4 H4B 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?

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 C3 C4 -166.17(10) . . . . ?
S1 N1 C2 C1 166.68(10) . . . . ?
S1 C5 C6 C7 -172.94(10) . . . . ?
O5 C11 C12 C7 -177.64(12) . . . . ?
O4 C10 C11 O5 -1.46(17) . . . . ?
O4 C10 C11 C12 179.67(11) . . . . ?
O2 S1 N1 C3 179.61(10) . . . . ?
O2 S1 N1 C2 -45.60(12) . . . . ?
O2 S1 C5 C6 -63.77(12) . . . . ?
O3 S1 N1 C3 51.59(11) . . . . ?
O3 S1 N1 C2 -173.63(10) . . . . ?
O3 S1 C5 C6 66.70(12) . . . . ?
N1 S1 C5 C6 -178.56(10) . . . . ?
N1 C3 C4 O1 -57.81(16) . . . . ?
N1 C2 C1 O1 58.00(16) . . . . ?
C9 C10 C11 O5 177.49(12) . . . . ?
C9 C10 C11 C12 -1.38(19) . . . . ?
C10 C9 C8 C7 0.8(2) . . . . ?
C10 C11 C12 C7 1.1(2) . . . . ?
C12 C7 C8 C9 -1.1(2) . . . . ?
C12 C7 C6 C5 137.21(14) . . . . ?
C8 C9 C10 O4 179.28(13) . . . . ?
C8 C9 C10 C11 0.5(2) . . . . ?
C8 C7 C12 C11 0.1(2) . . . . ?
C8 C7 C6 C5 -43.8(2) . . . . ?
C3 N1 C2 C1 -56.76(15) . . . . ?
C14 O5 C11 C10 -173.70(12) . . . . ?
C14 O5 C11 C12 5.09(19) . . . . ?
C5 S1 N1 C3 -64.46(11) . . . . ?
C5 S1 N1 C2 70.33(12) . . . . ?
C13 O4 C10 C9 4.68(19) . . . . ?
C13 O4 C10 C11 -176.44(11) . . . . ?
C2 N1 C3 C4 56.81(15) . . . . ?
C6 C7 C12 C11 179.11(13) . . . . ?
C6 C7 C8 C9 179.98(13) . . . . ?
C1 O1 C4 C3 60.11(16) . . . . ?
C4 O1 C1 C2 -60.35(16) . . . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.421
_oxdiff_exptl_absorpt_empirical_full_min 0.743
####################################################################### 
# 
# 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_hpd173
_database_code_depnum_ccdc_archive 'CCDC 2042739'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman'
;University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2020-11-05 deposited with the CCDC.	2021-04-06 downloaded from the CCDC.
;
_audit_creation_date             2020-07-27
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H17 N O3 S'
_chemical_formula_sum            'C13 H17 N O3 S'
_chemical_formula_weight         267.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S'
_chemical_oxdiff_usercomment     'VNY 184-6'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   23.1972(2)
_cell_length_b                   6.10055(7)
_cell_length_c                   9.24200(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.2932(9)
_cell_angle_gamma                90
_cell_volume                     1307.87(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8340
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.1000
_cell_measurement_theta_min      3.8050
_shelx_estimated_absorpt_T_max   0.888
_shelx_estimated_absorpt_T_min   0.634
_exptl_absorpt_coefficient_mu    2.213
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.515
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             568
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 -2 5 0.0803
4 3 3 0.0748
0 1 -6 0.0907
-4 -3 -4 0.0835
3 -2 5 0.0722
14 -1 -1 0.0283
-14 1 1 0.0172

_exptl_crystal_size_max          0.227
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.055
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
-2.3801 -2.4334 4.6413 -0.0453 -0.1956 0.9796
4.3292 3.3339 2.7318 0.2337 0.9723 -0.0089
0.3887 0.8943 -5.8421 -0.0615 -0.2485 -0.9667
-3.7650 -2.7343 -4.0645 -0.2262 -0.9387 -0.2602
2.7005 -2.0791 4.9851 0.2850 -0.0703 0.9560
14.4201 -0.9285 -1.0316 0.9626 -0.2312 -0.1410
-14.3271 0.7567 1.4759 -0.9473 0.2273 0.2256

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15264
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.443
_diffrn_reflns_theta_min         3.811
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -75.00  26.00   0.50    0.05    --  -46.75  86.00 155.00  202
  2  ω    -21.00  75.00   0.50    0.05    --   46.75 -86.00  37.00  192
  3  ω   -160.00 -79.00   0.50    0.19    --  -88.50 -86.00  37.00  162
  4  ω   -116.00 -15.00   0.50    0.19    --  -88.50  86.00 155.00  202
  5  ω    101.00 178.00   0.50    0.19    --  106.69  86.00 155.00  154
  6  ω   -119.00 -83.00   0.50    0.05    --  -46.75 -57.00  60.00   72
  7  ω   -119.00 -87.00   0.50    0.05    --  -46.75-125.00-150.00   64
  8  ω   -119.00 -83.00   0.50    0.05    --  -46.75 -57.00  30.00   72
  9  ω   -119.00 -87.00   0.50    0.05    --  -46.75-125.00-180.00   64
 10  ω   -160.00-101.00   0.50    0.19    --  -88.50 -77.00 -60.00  118
 11  ω    -51.00 -16.00   0.50    0.19    --  -88.50  45.00-120.00   70
 12  ω    -51.00 -16.00   0.50    0.19    --  -88.50  45.00 -60.00   70
 13  ω    -51.00 -16.00   0.50    0.19    --  -88.50  45.00   0.00   70
 14  ω     34.00  71.00   0.50    0.19    --  106.69 -61.00  90.00   74
 15  ω     91.00 178.00   0.50    0.19    --  106.69  30.00  90.00  174
 16  ω     34.00  71.00   0.50    0.19    --  106.69 -61.00 120.00   74
 17  ω     34.00 101.00   0.50    0.19    --  106.69 -77.00 -60.00  134
 18  ω     34.00  71.00   0.50    0.19    --  106.69 -61.00  60.00   74
 19  ω     34.00 105.00   0.50    0.19    --  106.69 -94.00   0.00  142
 20  ω     91.00 178.00   0.50    0.19    --  106.69  30.00 -30.00  174
 21  ω     92.00 178.00   0.50    0.19    --  106.69  45.00 120.00  172
 22  ω     34.00 135.00   0.50    0.19    --  106.69 -86.00  37.00  202
 23  ω   -121.00 -32.00   0.50    0.05    --  -46.75 -37.00-180.00  178
 24  ω   -121.00 -32.00   0.50    0.05    --  -46.75 -37.00  90.00  178
 25  ω   -121.00 -32.00   0.50    0.05    --  -46.75 -37.00   0.00  178
 26  ω   -121.00 -32.00   0.50    0.05    --  -46.75 -37.00 -90.00  178
 27  ω    -29.00  30.00   0.50    0.05    --   46.75 -19.00-150.00  118
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0659650000
_diffrn_orient_matrix_UB_12      -0.0246741000
_diffrn_orient_matrix_UB_13      0.0111399000
_diffrn_orient_matrix_UB_21      0.0038687000
_diffrn_orient_matrix_UB_22      0.2234998000
_diffrn_orient_matrix_UB_23      0.0770158000
_diffrn_orient_matrix_UB_31      -0.0066279000
_diffrn_orient_matrix_UB_32      -0.1148870000
_diffrn_orient_matrix_UB_33      0.1474374000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2450
_reflns_number_total             2668
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT n/a (Sheldrick, 2015)'
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2668
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0343
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0527P)²+0.5396P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.0974
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C13(H13A,H13B), C2(H2A,H2B), C3(H3A,H3B), C1(H1A,H1B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), C10(H10), C9(H9)
;
_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 0.71404(2) 0.35340(5) 0.51150(3) 0.01883(13) Uani 1 1 d . . . . .
O3 O 0.70627(5) 0.12238(16) 0.53440(11) 0.0238(2) Uani 1 1 d . . . . .
O2 O 0.73035(5) 0.48876(17) 0.63239(10) 0.0254(2) Uani 1 1 d . . . . .
O1 O 0.54570(5) 0.6045(2) 0.35520(14) 0.0360(3) Uani 1 1 d . . . . .
N1 N 0.65250(5) 0.4484(2) 0.45263(13) 0.0217(3) Uani 1 1 d . . . . .
C5 C 0.76570(6) 0.3806(2) 0.37277(15) 0.0197(3) Uani 1 1 d . . . . .
H5 H 0.749607 0.309110 0.283959 0.024 Uiso 1 1 calc R U . . .
C12 C 0.84090(6) 0.5890(3) 0.27131(15) 0.0227(3) Uani 1 1 d . . . . .
C6 C 0.82311(6) 0.2652(2) 0.41014(16) 0.0236(3) Uani 1 1 d . . . . .
H6A H 0.833104 0.281827 0.513837 0.028 Uiso 1 1 calc R U . . .
H6B H 0.821907 0.107515 0.385120 0.028 Uiso 1 1 calc R U . . .
C7 C 0.86447(6) 0.3890(2) 0.31485(16) 0.0238(3) Uani 1 1 d . . . . .
C13 C 0.78121(6) 0.6187(2) 0.33319(16) 0.0231(3) Uani 1 1 d . . . . .
H13A H 0.754140 0.679672 0.260484 0.028 Uiso 1 1 calc R U . . .
H13B H 0.781790 0.714508 0.419623 0.028 Uiso 1 1 calc R U . . .
C2 C 0.62131(7) 0.3310(3) 0.33773(17) 0.0276(3) Uani 1 1 d . . . . .
H2A H 0.629168 0.171797 0.344064 0.033 Uiso 1 1 calc R U . . .
H2B H 0.633768 0.383767 0.241530 0.033 Uiso 1 1 calc R U . . .
C8 C 0.91890(7) 0.3267(3) 0.26853(19) 0.0317(4) Uani 1 1 d . . . . .
H8 H 0.935204 0.191371 0.298846 0.038 Uiso 1 1 calc R U . . .
C11 C 0.87147(7) 0.7283(3) 0.18101(18) 0.0295(3) Uani 1 1 d . . . . .
H11 H 0.855508 0.864835 0.151779 0.035 Uiso 1 1 calc R U . . .
C3 C 0.64122(7) 0.6847(3) 0.4517(2) 0.0312(4) Uani 1 1 d . . . . .
H3A H 0.654502 0.750343 0.359771 0.037 Uiso 1 1 calc R U . . .
H3B H 0.661870 0.756741 0.532745 0.037 Uiso 1 1 calc R U . . .
C1 C 0.55786(7) 0.3749(3) 0.35850(19) 0.0336(4) Uani 1 1 d . . . . .
H1A H 0.535624 0.300566 0.281063 0.040 Uiso 1 1 calc R U . . .
H1B H 0.545494 0.313498 0.452513 0.040 Uiso 1 1 calc R U . . .
C10 C 0.92594(7) 0.6647(3) 0.1339(2) 0.0348(4) Uani 1 1 d . . . . .
H10 H 0.947232 0.758513 0.071936 0.042 Uiso 1 1 calc R U . . .
C4 C 0.57702(7) 0.7146(3) 0.4676(2) 0.0357(4) Uani 1 1 d . . . . .
H4A H 0.564823 0.656542 0.562715 0.043 Uiso 1 1 calc R U . . .
H4B H 0.567747 0.872949 0.464978 0.043 Uiso 1 1 calc R U . . .
C9 C 0.94928(7) 0.4663(3) 0.1767(2) 0.0372(4) Uani 1 1 d . . . . .
H9 H 0.986349 0.424604 0.143180 0.045 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.4367(10) . ?
S1 O2 1.4385(10) . ?
S1 N1 1.6315(12) . ?
S1 C5 1.7673(14) . ?
O1 C1 1.429(2) . ?
O1 C4 1.432(2) . ?
N1 C2 1.4684(19) . ?
N1 C3 1.4649(19) . ?
C5 H5 1.0000 . ?
C5 C6 1.5438(19) . ?
C5 C13 1.5408(19) . ?
C12 C7 1.395(2) . ?
C12 C13 1.512(2) . ?
C12 C11 1.388(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.508(2) . ?
C7 C8 1.388(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.509(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.396(2) . ?
C11 H11 0.9500 . ?
C11 C10 1.394(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.508(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C10 H10 0.9500 . ?
C10 C9 1.383(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C9 H9 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O2 118.78(6) . . ?
O3 S1 N1 106.71(6) . . ?
O3 S1 C5 106.56(7) . . ?
O2 S1 N1 106.34(6) . . ?
O2 S1 C5 109.45(6) . . ?
N1 S1 C5 108.67(6) . . ?
C1 O1 C4 110.17(13) . . ?
C2 N1 S1 119.66(10) . . ?
C3 N1 S1 120.50(10) . . ?
C3 N1 C2 112.85(12) . . ?
S1 C5 H5 107.6 . . ?
C6 C5 S1 112.47(10) . . ?
C6 C5 H5 107.6 . . ?
C13 C5 S1 114.88(10) . . ?
C13 C5 H5 107.6 . . ?
C13 C5 C6 106.29(11) . . ?
C7 C12 C13 110.73(13) . . ?
C11 C12 C7 120.53(14) . . ?
C11 C12 C13 128.73(14) . . ?
C5 C6 H6A 111.6 . . ?
C5 C6 H6B 111.6 . . ?
H6A C6 H6B 109.4 . . ?
C7 C6 C5 101.05(11) . . ?
C7 C6 H6A 111.6 . . ?
C7 C6 H6B 111.6 . . ?
C12 C7 C6 110.89(13) . . ?
C8 C7 C12 120.40(14) . . ?
C8 C7 C6 128.70(14) . . ?
C5 C13 H13A 111.6 . . ?
C5 C13 H13B 111.6 . . ?
C12 C13 C5 101.10(12) . . ?
C12 C13 H13A 111.6 . . ?
C12 C13 H13B 111.6 . . ?
H13A C13 H13B 109.4 . . ?
N1 C2 H2A 110.2 . . ?
N1 C2 H2B 110.2 . . ?
N1 C2 C1 107.38(13) . . ?
H2A C2 H2B 108.5 . . ?
C1 C2 H2A 110.2 . . ?
C1 C2 H2B 110.2 . . ?
C7 C8 H8 120.5 . . ?
C7 C8 C9 118.91(16) . . ?
C9 C8 H8 120.5 . . ?
C12 C11 H11 120.5 . . ?
C12 C11 C10 118.93(15) . . ?
C10 C11 H11 120.5 . . ?
N1 C3 H3A 110.3 . . ?
N1 C3 H3B 110.3 . . ?
N1 C3 C4 107.16(13) . . ?
H3A C3 H3B 108.5 . . ?
C4 C3 H3A 110.3 . . ?
C4 C3 H3B 110.3 . . ?
O1 C1 C2 111.32(14) . . ?
O1 C1 H1A 109.4 . . ?
O1 C1 H1B 109.4 . . ?
C2 C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
C11 C10 H10 119.7 . . ?
C9 C10 C11 120.60(15) . . ?
C9 C10 H10 119.7 . . ?
O1 C4 C3 111.71(14) . . ?
O1 C4 H4A 109.3 . . ?
O1 C4 H4B 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.63(15) . . ?
C10 C9 H9 119.7 . . ?

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 C2 C1 150.95(11) . . . . ?
S1 N1 C3 C4 -151.48(12) . . . . ?
S1 C5 C6 C7 -156.71(10) . . . . ?
S1 C5 C13 C12 155.19(10) . . . . ?
O3 S1 N1 C2 -46.21(12) . . . . ?
O3 S1 N1 C3 165.13(12) . . . . ?
O3 S1 C5 C6 -57.16(11) . . . . ?
O3 S1 C5 C13 -178.92(10) . . . . ?
O2 S1 N1 C2 -173.93(11) . . . . ?
O2 S1 N1 C3 37.40(13) . . . . ?
O2 S1 C5 C6 72.46(11) . . . . ?
O2 S1 C5 C13 -49.31(12) . . . . ?
N1 S1 C5 C6 -171.81(10) . . . . ?
N1 S1 C5 C13 66.42(11) . . . . ?
N1 C2 C1 O1 57.72(17) . . . . ?
N1 C3 C4 O1 -57.56(18) . . . . ?
C5 S1 N1 C2 68.34(12) . . . . ?
C5 S1 N1 C3 -80.32(13) . . . . ?
C5 C6 C7 C12 18.85(15) . . . . ?
C5 C6 C7 C8 -160.21(16) . . . . ?
C12 C7 C8 C9 -0.7(2) . . . . ?
C12 C11 C10 C9 -0.2(3) . . . . ?
C6 C5 C13 C12 30.13(14) . . . . ?
C6 C7 C8 C9 178.32(15) . . . . ?
C7 C12 C13 C5 -18.76(15) . . . . ?
C7 C12 C11 C10 0.3(2) . . . . ?
C7 C8 C9 C10 0.8(3) . . . . ?
C13 C5 C6 C7 -30.18(14) . . . . ?
C13 C12 C7 C6 -0.08(17) . . . . ?
C13 C12 C7 C8 179.06(14) . . . . ?
C13 C12 C11 C10 -178.46(16) . . . . ?
C2 N1 C3 C4 57.89(17) . . . . ?
C11 C12 C7 C6 -179.08(13) . . . . ?
C11 C12 C7 C8 0.1(2) . . . . ?
C11 C12 C13 C5 160.14(15) . . . . ?
C11 C10 C9 C8 -0.4(3) . . . . ?
C3 N1 C2 C1 -58.14(17) . . . . ?
C1 O1 C4 C3 59.79(18) . . . . ?
C4 O1 C1 C2 -59.68(18) . . . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_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 1.338
_oxdiff_exptl_absorpt_empirical_full_min 0.775
####################################################################### 
# 
# 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_hpd185
_database_code_depnum_ccdc_archive 'CCDC 2042742'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman'
;University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2020-11-05 deposited with the CCDC.	2021-04-06 downloaded from the CCDC.
;
_audit_creation_date             2020-08-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6143)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H33 N O9 S'
_chemical_formula_sum            'C26 H33 N O9 S'
_chemical_formula_weight         535.59
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S'
_chemical_oxdiff_usercomment     206-3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   22.5244(2)
_cell_length_b                   10.26708(10)
_cell_length_c                   12.02634(11)
_cell_angle_alpha                90
_cell_angle_beta                 96.6693(9)
_cell_angle_gamma                90
_cell_volume                     2762.38(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13114
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      75.3520
_cell_measurement_theta_min      3.7010
_shelx_estimated_absorpt_T_max   0.928
_shelx_estimated_absorpt_T_min   0.731
_exptl_absorpt_coefficient_mu    1.482
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.506
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1136
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
14 3 -1 0.0836
-8 5 -1 0.0889
-14 -1 1 0.1030
4 -6 1 0.0955
14 1 -1 0.0677
0 1 8 0.0374
-14 -1 3 0.0966
1 -1 -8 0.0093

_exptl_crystal_size_max          0.225
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.051
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
13.5031 2.5568 -0.9925 0.0456 0.1821 0.9822
-8.2119 5.3393 -1.0926 0.2149 0.8967 -0.3869
-14.4198 -1.0941 0.6573 0.0089 0.0447 -0.9990
3.8654 -6.2633 1.4370 -0.2331 -0.9701 0.0676
14.3195 1.2532 -1.4857 0.0991 -0.0220 0.9948
-0.3777 1.4257 7.5933 -0.9715 0.2336 0.0410
-14.1014 -1.0248 2.5469 -0.2366 0.0551 -0.9700
1.0925 -1.3569 -7.6351 0.9723 -0.2337 0.0090

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16441
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.582
_diffrn_reflns_theta_min         3.700
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -82.00  -1.00   0.50    0.08    --  -46.87 110.00 -43.00  162
  2  ω     23.00  88.00   0.50    0.08    --   46.87-110.00-138.00  130
  3  ω    -82.00 -15.00   0.50    0.32    --  -88.50 110.00 -43.00  134
  4  ω   -160.00 -82.00   0.50    0.32    --  -88.50-110.00-138.00  156
  5  ω     34.00 107.00   0.50    0.32    --  106.69-110.00-138.00  146
  6  ω    103.00 178.00   0.50    0.32    --  106.69 110.00 -43.00  150
  7  ω   -120.00 -83.00   0.50    0.08    --  -46.87 -57.00  30.00   74
  8  ω   -120.00 -83.00   0.50    0.08    --  -46.87 -57.00-180.00   74
  9  ω   -120.00 -87.00   0.50    0.08    --  -46.87-125.00  30.00   66
 10  ω   -120.00 -83.00   0.50    0.08    --  -46.87 -57.00 -90.00   74
 11  ω     83.00 120.00   0.50    0.08    --   46.87  57.00   0.00   74
 12  ω    -28.00  30.00   0.50    0.08    --   46.87 -19.00 120.00  116
 13  ω    -51.00 -16.00   0.50    0.32    --  -88.50  45.00 -60.00   70
 14  ω    -71.00 -15.00   0.50    0.32    --  -88.50  61.00 150.00  112
 15  ω   -160.00-101.00   0.50    0.32    --  -88.50 -77.00 -90.00  118
 16  ω    -51.00 -16.00   0.50    0.32    --  -88.50  45.00-120.00   70
 17  ω    -51.00 -16.00   0.50    0.32    --  -88.50  45.00   0.00   70
 18  ω    -51.00 -16.00   0.50    0.32    --  -88.50  45.00 150.00   70
 19  ω    -51.00 -16.00   0.50    0.32    --  -88.50  45.00-180.00   70
 20  ω    -51.00 -16.00   0.50    0.32    --  -88.50  45.00 -90.00   70
 21  ω    -51.00 -16.00   0.50    0.32    --  -88.50  45.00  90.00   70
 22  ω    -51.00 -16.00   0.50    0.32    --  -88.50  45.00 120.00   70
 23  ω     34.00  71.00   0.50    0.32    --  106.69 -61.00  30.00   74
 24  ω     34.00 105.00   0.50    0.32    --  106.69 -94.00-120.00  142
 25  ω     34.00 111.00   0.50    0.32    --  106.69-125.00 -30.00  154
 26  ω     34.00  71.00   0.50    0.32    --  106.69 -61.00   0.00   74
 27  ω     34.00 111.00   0.50    0.32    --  106.69-125.00  60.00  154
 28  ω     34.00  71.00   0.50    0.32    --  106.69 -61.00 -90.00   74
 29  ω   -121.00 -32.00   0.50    0.08    --  -46.87 -37.00 -90.00  178
 30  ω   -121.00 -32.00   0.50    0.08    --  -46.87 -37.00-180.00  178
 31  ω     32.00  67.00   0.50    0.08    --   46.87  37.00  60.00   70
 32  ω     32.00 121.00   0.50    0.08    --   46.87  37.00 120.00  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0067595000
_diffrn_orient_matrix_UB_12      0.0034706000
_diffrn_orient_matrix_UB_13      -0.1289235000
_diffrn_orient_matrix_UB_21      -0.0141181000
_diffrn_orient_matrix_UB_22      0.1467499000
_diffrn_orient_matrix_UB_23      0.0025156000
_diffrn_orient_matrix_UB_31      0.0670384000
_diffrn_orient_matrix_UB_32      0.0312296000
_diffrn_orient_matrix_UB_33      0.0028649000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.891
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.938
_reflns_number_gt                4809
_reflns_number_total             4895
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.072(19)
_refine_ls_extinction_coef       0.00072(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         4895
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0355
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0588P)²+2.3316P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.0944
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.928(19)
 0.072(19)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C2(H2), C10(H10), C9(H9), C12(H12)
3.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C7(H7A,H7B), C4(H4A,H4B), C22(H22A,H22B), C21(H21A,H21B),
 C15(H15A,H15B), C20(H20A,H20B), C3(H3A,H3B)
3.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C13(H13)
3.d X=CH2 refined with riding coordinates:
 C19(H19A,H19B)
3.e Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C18(H18A,H18B,H18C)
;
_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 0.40586(3) 0.58083(7) 0.63090(5) 0.01966(16) Uani 1 1 d . . . . .
O8 O 0.35959(9) 0.6701(2) 0.58809(16) 0.0249(4) Uani 1 1 d . . . . .
O7 O 0.46458(8) 0.5926(2) 0.59701(16) 0.0271(4) Uani 1 1 d . . . . .
O3 O 0.25776(10) 0.4098(2) 0.85947(17) 0.0299(5) Uani 1 1 d . . . . .
O6 O 0.40038(9) 0.1848(2) 0.23390(18) 0.0299(5) Uani 1 1 d . . . . .
O1 O 0.29483(9) 0.1947(2) 0.56361(18) 0.0279(5) Uani 1 1 d . . . . .
O9 O 0.45559(9) 0.7992(2) 0.90079(17) 0.0306(5) Uani 1 1 d . . . . .
O5 O 0.49168(9) 0.2753(3) 0.27731(19) 0.0342(5) Uani 1 1 d . . . . .
O2 O 0.33422(12) 0.0615(3) 0.6991(2) 0.0424(6) Uani 1 1 d . . . . .
N1 N 0.41086(9) 0.5852(3) 0.76813(17) 0.0223(5) Uani 1 1 d . . . . .
O4 O 0.19231(14) 0.3045(3) 0.9546(3) 0.0575(8) Uani 1 1 d . . . . .
C6 C 0.37839(12) 0.4199(3) 0.2720(2) 0.0231(6) Uani 1 1 d . . . . .
C2 C 0.29454(12) 0.3941(3) 0.4498(2) 0.0228(6) Uani 1 1 d . . . . .
H2 H 0.2810 0.4868 0.4504 0.027 Uiso 1 1 calc R U . . .
C1 C 0.27792(12) 0.3354(3) 0.5566(2) 0.0230(6) Uani 1 1 d . . . . .
C5 C 0.37120(13) 0.2767(3) 0.3026(2) 0.0250(6) Uani 1 1 d . . . . .
C8 C 0.36392(11) 0.3994(3) 0.4665(2) 0.0201(6) Uani 1 1 d . . . . .
C23 C 0.37101(12) 0.6719(3) 0.8220(2) 0.0250(6) Uani 1 1 d . . . . .
H23A H 0.3643 0.6359 0.8959 0.030 Uiso 1 1 calc R U . . .
H23B H 0.3319 0.6776 0.7754 0.030 Uiso 1 1 calc R U . . .
C16 C 0.31809(14) 0.1691(3) 0.6699(3) 0.0298(7) Uani 1 1 d . . . . .
C7 C 0.38608(12) 0.4965(3) 0.3807(2) 0.0207(6) Uani 1 1 d . . . . .
H7A H 0.3615 0.5767 0.3747 0.025 Uiso 1 1 calc R U . . .
H7B H 0.4285 0.5204 0.4020 0.025 Uiso 1 1 calc R U . . .
C4 C 0.30557(13) 0.2359(3) 0.2858(3) 0.0294(7) Uani 1 1 d . . . . .
H4A H 0.3010 0.1502 0.3214 0.035 Uiso 1 1 calc R U . . .
H4B H 0.2922 0.2272 0.2048 0.035 Uiso 1 1 calc R U . . .
C17 C 0.45984(15) 0.1931(4) 0.2298(3) 0.0331(7) Uani 1 1 d . . . . .
C22 C 0.39826(14) 0.8066(3) 0.8371(3) 0.0307(7) Uani 1 1 d . . . . .
H22A H 0.4022 0.8454 0.7629 0.037 Uiso 1 1 calc R U . . .
H22B H 0.3718 0.8634 0.8761 0.037 Uiso 1 1 calc R U . . .
C10 C 0.32076(12) 0.3963(3) 0.6494(2) 0.0221(6) Uani 1 1 d . . . . .
H10 H 0.3043 0.4806 0.6741 0.027 Uiso 1 1 calc R U . . .
C9 C 0.37953(12) 0.4200(3) 0.5957(2) 0.0203(6) Uani 1 1 d . . . . .
H9 H 0.4104 0.3550 0.6257 0.024 Uiso 1 1 calc R U . . .
C21 C 0.49543(13) 0.7184(3) 0.8478(3) 0.0295(7) Uani 1 1 d . . . . .
H21A H 0.5347 0.7156 0.8944 0.035 Uiso 1 1 calc R U . . .
H21B H 0.5016 0.7563 0.7743 0.035 Uiso 1 1 calc R U . . .
C15 C 0.39235(12) 0.2720(3) 0.4278(2) 0.0227(6) Uani 1 1 d . . . . .
H15A H 0.4365 0.2739 0.4428 0.027 Uiso 1 1 calc R U . . .
H15B H 0.3769 0.1943 0.4637 0.027 Uiso 1 1 calc R U . . .
C11 C 0.31932(13) 0.2933(3) 0.7403(2) 0.0264(6) Uani 1 1 d . . . . .
C19 C 0.37469(13) 0.4664(3) 0.1690(2) 0.0295(7) Uani 1 1 d . . . . .
H19A H 0.3769 0.5577 0.1571 0.035 Uiso 1 1 calc R U . . .
H19B H 0.3699 0.4087 0.1069 0.035 Uiso 1 1 calc R U . . .
C14 C 0.21463(13) 0.3438(3) 0.5849(3) 0.0286(7) Uani 1 1 d . . . . .
H14 H 0.1823 0.3620 0.5291 0.034 Uiso 1 1 calc R U . . .
C20 C 0.47136(11) 0.5810(4) 0.8309(2) 0.0256(6) Uani 1 1 d . . . . .
H20A H 0.4983 0.5292 0.7887 0.031 Uiso 1 1 calc R U . . .
H20B H 0.4696 0.5388 0.9044 0.031 Uiso 1 1 calc R U . . .
C3 C 0.26644(13) 0.3376(3) 0.3375(3) 0.0282(6) Uani 1 1 d . . . . .
H3A H 0.2580 0.4101 0.2837 0.034 Uiso 1 1 calc R U . . .
H3B H 0.2278 0.2967 0.3487 0.034 Uiso 1 1 calc R U . . .
C25 C 0.22214(15) 0.3996(4) 0.9418(3) 0.0333(7) Uani 1 1 d . . . . .
C12 C 0.25636(14) 0.3004(3) 0.7817(3) 0.0302(7) Uani 1 1 d . . . . .
H12 H 0.2485 0.2181 0.8219 0.036 Uiso 1 1 calc R U . . .
C13 C 0.20586(14) 0.3249(4) 0.6903(3) 0.0332(7) Uani 1 1 d . . . . .
H13 H 0.1661 0.3267 0.7094 0.040 Uiso 1 1 calc R U . . .
C24 C 0.36927(14) 0.2905(4) 0.8375(3) 0.0344(7) Uani 1 1 d . . . . .
H24A H 0.3638 0.2153 0.8854 0.052 Uiso 1 1 calc R U . . .
H24B H 0.3682 0.3707 0.8813 0.052 Uiso 1 1 calc R U . . .
H24C H 0.4080 0.2835 0.8082 0.052 Uiso 1 1 calc R U . . .
C26 C 0.22239(17) 0.5223(4) 1.0080(3) 0.0383(8) Uani 1 1 d . . . . .
H26A H 0.2622 0.5620 1.0133 0.057 Uiso 1 1 calc R U . . .
H26B H 0.2123 0.5027 1.0833 0.057 Uiso 1 1 calc R U . . .
H26C H 0.1928 0.5829 0.9709 0.057 Uiso 1 1 calc R U . . .
C18 C 0.48010(19) 0.0881(5) 0.1560(4) 0.0555(10) Uani 1 1 d . . . . .
H18A H 0.4623 0.0048 0.1743 0.083 Uiso 1 1 calc R U . . .
H18B H 0.5238 0.0812 0.1680 0.083 Uiso 1 1 calc R U . . .
H18C H 0.4674 0.1096 0.0774 0.083 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 O8 1.437(2) . ?
S1 O7 1.4338(19) . ?
S1 N1 1.642(2) . ?
S1 C9 1.788(3) . ?
O3 C25 1.349(4) . ?
O3 C12 1.459(4) . ?
O6 C5 1.459(4) . ?
O6 C17 1.348(4) . ?
O1 C1 1.493(4) . ?
O1 C16 1.350(4) . ?
O9 C22 1.425(4) . ?
O9 C21 1.426(4) . ?
O5 C17 1.207(4) . ?
O2 C16 1.203(4) . ?
N1 C23 1.467(4) . ?
N1 C20 1.480(3) . ?
O4 C25 1.206(4) . ?
C6 C5 1.528(5) . ?
C6 C7 1.519(4) . ?
C6 C19 1.321(4) . ?
C2 H2 1.0000 . ?
C2 C1 1.504(4) . ?
C2 C8 1.553(4) . ?
C2 C3 1.537(4) . ?
C1 C10 1.522(4) . ?
C1 C14 1.506(4) . ?
C5 C4 1.527(4) . ?
C5 C15 1.527(4) . ?
C8 C7 1.558(4) . ?
C8 C9 1.568(4) . ?
C8 C15 1.551(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C22 1.516(5) . ?
C16 C11 1.529(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C3 1.543(5) . ?
C17 C18 1.502(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C10 H10 1.0000 . ?
C10 C9 1.558(4) . ?
C10 C11 1.524(4) . ?
C9 H9 1.0000 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C20 1.517(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C11 C12 1.558(4) . ?
C11 C24 1.526(4) . ?
C19 H19A 0.9500 . ?
C19 H19B 0.9500 . ?
C14 H14 0.9500 . ?
C14 C13 1.320(5) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C25 C26 1.489(5) . ?
C12 H12 1.0000 . ?
C12 C13 1.508(5) . ?
C13 H13 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
O8 S1 N1 107.75(12) . . ?
O8 S1 C9 107.28(13) . . ?
O7 S1 O8 119.92(14) . . ?
O7 S1 N1 109.00(11) . . ?
O7 S1 C9 107.60(13) . . ?
N1 S1 C9 104.20(13) . . ?
C25 O3 C12 116.1(3) . . ?
C17 O6 C5 119.6(2) . . ?
C16 O1 C1 108.1(2) . . ?
C22 O9 C21 111.7(2) . . ?
C23 N1 S1 119.12(19) . . ?
C23 N1 C20 111.5(2) . . ?
C20 N1 S1 117.61(17) . . ?
C7 C6 C5 107.2(2) . . ?
C19 C6 C5 125.2(3) . . ?
C19 C6 C7 127.4(3) . . ?
C1 C2 H2 105.6 . . ?
C1 C2 C8 104.5(2) . . ?
C1 C2 C3 118.7(3) . . ?
C8 C2 H2 105.6 . . ?
C3 C2 H2 105.6 . . ?
C3 C2 C8 115.6(2) . . ?
O1 C1 C2 110.4(2) . . ?
O1 C1 C10 102.7(2) . . ?
O1 C1 C14 106.5(2) . . ?
C2 C1 C10 105.2(2) . . ?
C2 C1 C14 120.4(3) . . ?
C14 C1 C10 110.3(2) . . ?
O6 C5 C6 114.7(2) . . ?
O6 C5 C4 103.9(2) . . ?
O6 C5 C15 115.4(2) . . ?
C4 C5 C6 111.1(3) . . ?
C15 C5 C6 103.8(2) . . ?
C15 C5 C4 107.9(2) . . ?
C2 C8 C7 109.4(2) . . ?
C2 C8 C9 103.8(2) . . ?
C7 C8 C9 121.2(2) . . ?
C15 C8 C2 112.1(2) . . ?
C15 C8 C7 99.5(2) . . ?
C15 C8 C9 111.0(2) . . ?
N1 C23 H23A 109.6 . . ?
N1 C23 H23B 109.6 . . ?
N1 C23 C22 110.3(2) . . ?
H23A C23 H23B 108.1 . . ?
C22 C23 H23A 109.6 . . ?
C22 C23 H23B 109.6 . . ?
O1 C16 C11 110.0(3) . . ?
O2 C16 O1 121.8(3) . . ?
O2 C16 C11 128.2(3) . . ?
C6 C7 C8 103.0(2) . . ?
C6 C7 H7A 111.2 . . ?
C6 C7 H7B 111.2 . . ?
C8 C7 H7A 111.2 . . ?
C8 C7 H7B 111.2 . . ?
H7A C7 H7B 109.1 . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C5 C4 C3 110.5(3) . . ?
H4A C4 H4B 108.1 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
O6 C17 C18 110.3(3) . . ?
O5 C17 O6 124.4(3) . . ?
O5 C17 C18 125.2(3) . . ?
O9 C22 C23 110.2(3) . . ?
O9 C22 H22A 109.6 . . ?
O9 C22 H22B 109.6 . . ?
C23 C22 H22A 109.6 . . ?
C23 C22 H22B 109.6 . . ?
H22A C22 H22B 108.1 . . ?
C1 C10 H10 110.4 . . ?
C1 C10 C9 104.9(2) . . ?
C1 C10 C11 100.2(2) . . ?
C9 C10 H10 110.4 . . ?
C11 C10 H10 110.4 . . ?
C11 C10 C9 119.7(2) . . ?
S1 C9 H9 109.5 . . ?
C8 C9 S1 112.89(19) . . ?
C8 C9 H9 109.5 . . ?
C10 C9 S1 108.7(2) . . ?
C10 C9 C8 106.6(2) . . ?
C10 C9 H9 109.5 . . ?
O9 C21 H21A 109.3 . . ?
O9 C21 H21B 109.3 . . ?
O9 C21 C20 111.6(2) . . ?
H21A C21 H21B 108.0 . . ?
C20 C21 H21A 109.3 . . ?
C20 C21 H21B 109.3 . . ?
C5 C15 C8 100.2(2) . . ?
C5 C15 H15A 111.7 . . ?
C5 C15 H15B 111.7 . . ?
C8 C15 H15A 111.7 . . ?
C8 C15 H15B 111.7 . . ?
H15A C15 H15B 109.5 . . ?
C16 C11 C12 104.9(2) . . ?
C10 C11 C16 100.5(2) . . ?
C10 C11 C12 107.0(2) . . ?
C10 C11 C24 119.2(3) . . ?
C24 C11 C16 111.9(3) . . ?
C24 C11 C12 111.9(2) . . ?
C6 C19 H19A 120.0 . . ?
C6 C19 H19B 120.0 . . ?
H19A C19 H19B 120.0 . . ?
C1 C14 H14 121.3 . . ?
C13 C14 C1 117.4(3) . . ?
C13 C14 H14 121.3 . . ?
N1 C20 C21 109.6(3) . . ?
N1 C20 H20A 109.8 . . ?
N1 C20 H20B 109.8 . . ?
C21 C20 H20A 109.8 . . ?
C21 C20 H20B 109.8 . . ?
H20A C20 H20B 108.2 . . ?
C2 C3 C4 114.4(2) . . ?
C2 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
C4 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
O3 C25 C26 111.2(3) . . ?
O4 C25 O3 123.0(3) . . ?
O4 C25 C26 125.8(3) . . ?
O3 C12 C11 106.8(2) . . ?
O3 C12 H12 109.4 . . ?
O3 C12 C13 107.3(3) . . ?
C11 C12 H12 109.4 . . ?
C13 C12 C11 114.3(2) . . ?
C13 C12 H12 109.4 . . ?
C14 C13 C12 122.7(3) . . ?
C14 C13 H13 118.7 . . ?
C12 C13 H13 118.7 . . ?
C11 C24 H24A 109.5 . . ?
C11 C24 H24B 109.5 . . ?
C11 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C23 C22 -86.9(3) . . . . ?
S1 N1 C20 C21 89.1(3) . . . . ?
O8 S1 N1 C23 -0.1(3) . . . . ?
O8 S1 N1 C20 -140.0(2) . . . . ?
O8 S1 C9 C8 58.9(2) . . . . ?
O8 S1 C9 C10 -59.2(2) . . . . ?
O7 S1 N1 C23 131.5(2) . . . . ?
O7 S1 N1 C20 -8.4(3) . . . . ?
O7 S1 C9 C8 -71.4(2) . . . . ?
O7 S1 C9 C10 170.49(18) . . . . ?
O3 C12 C13 C14 115.6(3) . . . . ?
O6 C5 C4 C3 -170.6(3) . . . . ?
O6 C5 C15 C8 167.3(2) . . . . ?
O1 C1 C10 C9 83.6(2) . . . . ?
O1 C1 C10 C11 -41.1(2) . . . . ?
O1 C1 C14 C13 72.1(4) . . . . ?
O1 C16 C11 C10 -24.9(3) . . . . ?
O1 C16 C11 C12 86.1(3) . . . . ?
O1 C16 C11 C24 -152.4(2) . . . . ?
O9 C21 C20 N1 55.0(3) . . . . ?
O2 C16 C11 C10 155.6(3) . . . . ?
O2 C16 C11 C12 -93.4(4) . . . . ?
O2 C16 C11 C24 28.1(4) . . . . ?
N1 S1 C9 C8 172.96(17) . . . . ?
N1 S1 C9 C10 54.9(2) . . . . ?
N1 C23 C22 O9 -57.2(3) . . . . ?
C6 C5 C4 C3 -46.8(3) . . . . ?
C6 C5 C15 C8 41.0(2) . . . . ?
C2 C1 C10 C9 -32.0(3) . . . . ?
C2 C1 C10 C11 -156.6(2) . . . . ?
C2 C1 C14 C13 -161.3(3) . . . . ?
C2 C8 C7 C6 -76.4(3) . . . . ?
C2 C8 C9 S1 -107.6(2) . . . . ?
C2 C8 C9 C10 11.7(3) . . . . ?
C2 C8 C15 C5 64.9(3) . . . . ?
C1 O1 C16 O2 178.3(3) . . . . ?
C1 O1 C16 C11 -1.2(3) . . . . ?
C1 C2 C8 C7 -162.1(2) . . . . ?
C1 C2 C8 C9 -31.4(3) . . . . ?
C1 C2 C8 C15 88.5(3) . . . . ?
C1 C2 C3 C4 -96.1(3) . . . . ?
C1 C10 C9 S1 133.9(2) . . . . ?
C1 C10 C9 C8 11.9(3) . . . . ?
C1 C10 C11 C16 39.2(3) . . . . ?
C1 C10 C11 C12 -70.1(3) . . . . ?
C1 C10 C11 C24 161.7(3) . . . . ?
C1 C14 C13 C12 2.2(5) . . . . ?
C5 O6 C17 O5 -2.3(5) . . . . ?
C5 O6 C17 C18 179.1(3) . . . . ?
C5 C6 C7 C8 -16.5(3) . . . . ?
C5 C4 C3 C2 -39.5(4) . . . . ?
C8 C2 C1 O1 -70.2(3) . . . . ?
C8 C2 C1 C10 39.9(3) . . . . ?
C8 C2 C1 C14 165.0(3) . . . . ?
C8 C2 C3 C4 29.3(4) . . . . ?
C23 N1 C20 C21 -53.7(3) . . . . ?
C16 O1 C1 C2 138.8(2) . . . . ?
C16 O1 C1 C10 27.1(3) . . . . ?
C16 O1 C1 C14 -88.9(3) . . . . ?
C16 C11 C12 O3 173.9(2) . . . . ?
C16 C11 C12 C13 -67.7(3) . . . . ?
C7 C6 C5 O6 -142.1(2) . . . . ?
C7 C6 C5 C4 100.4(3) . . . . ?
C7 C6 C5 C15 -15.3(3) . . . . ?
C7 C8 C9 S1 15.7(3) . . . . ?
C7 C8 C9 C10 135.0(3) . . . . ?
C7 C8 C15 C5 -50.7(2) . . . . ?
C4 C5 C15 C8 -77.0(3) . . . . ?
C17 O6 C5 C6 58.8(4) . . . . ?
C17 O6 C5 C4 -179.7(3) . . . . ?
C17 O6 C5 C15 -61.8(4) . . . . ?
C22 O9 C21 C20 -58.9(3) . . . . ?
C10 C1 C14 C13 -38.7(4) . . . . ?
C10 C11 C12 O3 -80.0(3) . . . . ?
C10 C11 C12 C13 38.5(3) . . . . ?
C9 S1 N1 C23 -113.8(2) . . . . ?
C9 S1 N1 C20 106.3(3) . . . . ?
C9 C8 C7 C6 163.0(2) . . . . ?
C9 C8 C15 C5 -179.5(2) . . . . ?
C9 C10 C11 C16 -74.5(3) . . . . ?
C9 C10 C11 C12 176.2(2) . . . . ?
C9 C10 C11 C24 48.0(4) . . . . ?
C21 O9 C22 C23 59.3(3) . . . . ?
C15 C5 C4 C3 66.4(3) . . . . ?
C15 C8 C7 C6 41.2(2) . . . . ?
C15 C8 C9 S1 131.8(2) . . . . ?
C15 C8 C9 C10 -108.9(2) . . . . ?
C11 C10 C9 S1 -114.9(3) . . . . ?
C11 C10 C9 C8 123.1(3) . . . . ?
C11 C12 C13 C14 -2.6(5) . . . . ?
C19 C6 C5 O6 41.7(4) . . . . ?
C19 C6 C5 C4 -75.8(3) . . . . ?
C19 C6 C5 C15 168.4(3) . . . . ?
C19 C6 C7 C8 159.7(3) . . . . ?
C14 C1 C10 C9 -163.2(3) . . . . ?
C14 C1 C10 C11 72.1(3) . . . . ?
C20 N1 C23 C22 55.2(3) . . . . ?
C3 C2 C1 O1 60.4(3) . . . . ?
C3 C2 C1 C10 170.5(3) . . . . ?
C3 C2 C1 C14 -64.4(4) . . . . ?
C3 C2 C8 C7 65.5(3) . . . . ?
C3 C2 C8 C9 -163.8(3) . . . . ?
C3 C2 C8 C15 -43.9(3) . . . . ?
C25 O3 C12 C11 -150.1(3) . . . . ?
C25 O3 C12 C13 87.0(3) . . . . ?
C12 O3 C25 O4 2.8(5) . . . . ?
C12 O3 C25 C26 -173.9(3) . . . . ?
C24 C11 C12 O3 52.3(3) . . . . ?
C24 C11 C12 C13 170.8(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.428 0.500 128.8 52.4 '1 CH2Cl2'
2 0.000 0.841 0.000 20.7 0.0 ?
3 0.500 -0.072 0.500 128.8 52.4 '1 CH2Cl2'
4 0.500 0.341 0.000 20.7 0.0 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_exptl_crystal_mounting_method 'nylon loop'
_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 1.356
_oxdiff_exptl_absorpt_empirical_full_min 0.815
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.928(19)
2 0.072(19)

####################################################################### 
# 
# 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_hpd171
_database_code_depnum_ccdc_archive 'CCDC 2042740'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman'
;University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2020-11-05 deposited with the CCDC.	2021-04-06 downloaded from the CCDC.
;
_audit_creation_date             2020-07-27
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H17 F2 N O3 S'
_chemical_formula_sum            'C10 H17 F2 N O3 S'
_chemical_formula_weight         269.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H S O N F'
_chemical_oxdiff_usercomment     'VNY 184-07'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   11.83783(11)
_cell_length_b                   10.04452(10)
_cell_length_c                   10.01996(9)
_cell_angle_alpha                90
_cell_angle_beta                 96.4304(8)
_cell_angle_gamma                90
_cell_volume                     1183.93(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9492
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.0450
_cell_measurement_theta_min      3.7540
_shelx_estimated_absorpt_T_max   0.718
_shelx_estimated_absorpt_T_min   0.562
_exptl_absorpt_coefficient_mu    2.690
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.534
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 -5 -2 0.0757
-5 5 -1 0.0602
1 6 1 0.0478
6 -4 2 0.0850
2 -6 0 0.0810
-2 -1 -6 0.1040
-7 -2 0 0.0761
2 1 6 0.0542
7 2 -2 0.0635

_exptl_crystal_size_max          0.242
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.132
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
-3.1905 -5.3713 -2.1960 -0.6185 0.1473 0.7719
-4.6533 4.8253 -1.4489 0.8792 -0.2122 0.4267
1.1426 6.2687 1.3885 0.8328 -0.1993 -0.5164
5.5895 -3.6489 2.0379 -0.7539 0.1824 -0.6311
1.5334 -6.3881 -0.1873 -0.9648 0.2317 0.1244
-2.2637 -1.0224 -5.8795 0.1399 0.5879 0.7967
-7.2829 -1.9930 0.0864 -0.1125 -0.4611 0.8802
1.5340 0.8394 6.1336 -0.1584 -0.6645 -0.7303
7.1401 1.8057 -2.2577 0.1746 0.7211 -0.6704

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13841
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.457
_diffrn_reflns_theta_min         3.758
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.964
_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   7.00   0.50    0.05    --  -46.87 103.00  44.00  174
  2  ω     15.00  84.00   0.50    0.05    --   46.87-103.00 -57.00  138
  3  ω    -81.00 -15.00   0.50    0.06    --  -88.50 103.00  44.00  132
  4  ω   -160.00 -84.00   0.50    0.06    --  -88.50-103.00 -57.00  152
  5  ω     34.00 106.00   0.50    0.06    --  106.69-103.00 -57.00  144
  6  ω    106.00 178.00   0.50    0.06    --  106.69 103.00  44.00  144
  7  ω   -120.00 -87.00   0.50    0.05    --  -46.87-125.00   0.00   66
  8  ω   -120.00 -83.00   0.50    0.05    --  -46.87 -57.00 -60.00   74
  9  ω   -120.00 -83.00   0.50    0.05    --  -46.87 -57.00-150.00   74
 10  ω   -120.00 -87.00   0.50    0.05    --  -46.87-125.00 120.00   66
 11  ω     83.00 120.00   0.50    0.05    --   46.87  57.00-150.00   74
 12  ω     83.00 120.00   0.50    0.05    --   46.87  57.00   0.00   74
 13  ω    -51.00 -16.00   0.50    0.06    --  -88.50  45.00  30.00   70
 14  ω   -160.00 -91.00   0.50    0.06    --  -88.50 -61.00 -30.00  138
 15  ω    -51.00 -16.00   0.50    0.06    --  -88.50  45.00  60.00   70
 16  ω    -51.00 -16.00   0.50    0.06    --  -88.50  45.00 -90.00   70
 17  ω    -51.00 -16.00   0.50    0.06    --  -88.50  45.00 150.00   70
 18  ω    -51.00 -16.00   0.50    0.06    --  -88.50  45.00-120.00   70
 19  ω     34.00  71.00   0.50    0.06    --  106.69 -61.00 -30.00   74
 20  ω     34.00 101.00   0.50    0.06    --  106.69 -77.00 -30.00  134
 21  ω     91.00 178.00   0.50    0.06    --  106.69  61.00  90.00  174
 22  ω     34.00 101.00   0.50    0.06    --  106.69 -77.00   0.00  134
 23  ω     34.00 101.00   0.50    0.06    --  106.69 -77.00 150.00  134
 24  ω     34.00  71.00   0.50    0.06    --  106.69 -61.00   0.00   74
 25  ω     34.00  71.00   0.50    0.06    --  106.69 -61.00-180.00   74
 26  ω     34.00  71.00   0.50    0.06    --  106.69 -61.00 150.00   74
 27  ω     34.00  71.00   0.50    0.06    --  106.69 -61.00 120.00   74
 28  ω   -121.00 -32.00   0.50    0.05    --  -46.87 -37.00 -30.00  178
 29  ω   -121.00 -32.00   0.50    0.05    --  -46.87 -37.00  90.00  178
 30  ω   -121.00 -32.00   0.50    0.05    --  -46.87 -37.00-180.00  178
 31  ω   -121.00 -46.00   0.50    0.05    --  -46.87 -37.00 -90.00  150
 32  ω     83.00 120.00   0.50    0.05    --   46.87  57.00  60.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0250221000
_diffrn_orient_matrix_UB_12      0.1461835000
_diffrn_orient_matrix_UB_13      -0.0395729000
_diffrn_orient_matrix_UB_21      0.0664407000
_diffrn_orient_matrix_UB_22      -0.0167314000
_diffrn_orient_matrix_UB_23      -0.1226683000
_diffrn_orient_matrix_UB_31      -0.1100030000
_diffrn_orient_matrix_UB_32      -0.0433608000
_diffrn_orient_matrix_UB_33      -0.0856180000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2287
_reflns_number_total             2397
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT n/a (Sheldrick, 2015)'
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0298
_refine_ls_restrained_S_all      1.075
_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)+(0.0332P)²+0.7191P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0759
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C6(H6A,H6B), C1(H1A,H1B), C7(H7A,H7B), C9(H9A,H9B), C4(H4A,
 H4B), C2(H2A,H2B), C3(H3A,H3B)
;
_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 0.22924(3) 0.41531(3) 0.48796(3) 0.01400(11) Uani 1 1 d . . . . .
F1 F 0.05484(7) 0.70053(8) 0.93906(8) 0.0216(2) Uani 1 1 d . . . . .
F2 F 0.21500(7) 0.59064(8) 0.95000(8) 0.0217(2) Uani 1 1 d . . . . .
O3 O 0.14234(8) 0.33159(10) 0.41991(9) 0.0190(2) Uani 1 1 d . . . . .
O2 O 0.28912(9) 0.50698(10) 0.41075(9) 0.0199(2) Uani 1 1 d . . . . .
O1 O 0.49517(9) 0.13892(11) 0.66739(12) 0.0280(3) Uani 1 1 d . . . . .
N1 N 0.32356(10) 0.31647(11) 0.56464(11) 0.0156(2) Uani 1 1 d . . . . .
C10 C 0.12735(12) 0.42274(13) 0.72020(14) 0.0165(3) Uani 1 1 d . . . . .
H10A H 0.196444 0.386806 0.772750 0.020 Uiso 1 1 calc R U . . .
H10B H 0.081658 0.346773 0.681220 0.020 Uiso 1 1 calc R U . . .
C6 C 0.23189(11) 0.63078(13) 0.66342(14) 0.0158(3) Uani 1 1 d . . . . .
H6A H 0.253571 0.686619 0.588956 0.019 Uiso 1 1 calc R U . . .
H6B H 0.302211 0.599576 0.717088 0.019 Uiso 1 1 calc R U . . .
C8 C 0.12128(12) 0.62630(14) 0.86160(13) 0.0161(3) Uani 1 1 d . . . . .
C5 C 0.16144(11) 0.51159(13) 0.60724(13) 0.0138(3) Uani 1 1 d . . . . .
H5 H 0.089612 0.547929 0.558718 0.017 Uiso 1 1 calc R U . . .
C1 C 0.29363(12) 0.18517(13) 0.61657(14) 0.0174(3) Uani 1 1 d . . . . .
H1A H 0.222702 0.151973 0.565696 0.021 Uiso 1 1 calc R U . . .
H1B H 0.281286 0.192507 0.712390 0.021 Uiso 1 1 calc R U . . .
C7 C 0.15975(12) 0.71209(14) 0.75205(14) 0.0165(3) Uani 1 1 d . . . . .
H7A H 0.205044 0.787698 0.792538 0.020 Uiso 1 1 calc R U . . .
H7B H 0.092581 0.748649 0.696269 0.020 Uiso 1 1 calc R U . . .
C9 C 0.05793(12) 0.50248(14) 0.81286(13) 0.0176(3) Uani 1 1 d . . . . .
H9A H -0.016257 0.527322 0.763592 0.021 Uiso 1 1 calc R U . . .
H9B H 0.043281 0.446884 0.890680 0.021 Uiso 1 1 calc R U . . .
C4 C 0.43213(12) 0.36756(14) 0.63016(15) 0.0210(3) Uani 1 1 d . . . . .
H4A H 0.426812 0.383187 0.726810 0.025 Uiso 1 1 calc R U . . .
H4B H 0.451247 0.452883 0.588621 0.025 Uiso 1 1 calc R U . . .
C2 C 0.39040(12) 0.09018(14) 0.60098(16) 0.0210(3) Uani 1 1 d . . . . .
H2A H 0.373228 0.002438 0.638944 0.025 Uiso 1 1 calc R U . . .
H2B H 0.397833 0.077821 0.504329 0.025 Uiso 1 1 calc R U . . .
C3 C 0.52273(13) 0.26467(16) 0.61277(19) 0.0297(4) Uani 1 1 d . . . . .
H3A H 0.530619 0.254154 0.516013 0.036 Uiso 1 1 calc R U . . .
H3B H 0.596555 0.295868 0.658200 0.036 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 O3 1.4398(10) . ?
S1 O2 1.4393(10) . ?
S1 N1 1.6219(12) . ?
S1 C5 1.7952(13) . ?
F1 C8 1.3834(15) . ?
F2 C8 1.3870(15) . ?
O1 C2 1.4267(18) . ?
O1 C3 1.4288(19) . ?
N1 C1 1.4754(17) . ?
N1 C4 1.4687(17) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C5 1.5306(18) . ?
C10 C9 1.5329(18) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C5 1.5298(18) . ?
C6 C7 1.5345(18) . ?
C8 C7 1.5055(19) . ?
C8 C9 1.5052(19) . ?
C5 H5 1.0000 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.5124(19) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C3 1.513(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 N1 106.51(6) . . ?
O3 S1 C5 106.32(6) . . ?
O2 S1 O3 119.20(6) . . ?
O2 S1 N1 106.97(6) . . ?
O2 S1 C5 107.28(6) . . ?
N1 S1 C5 110.47(6) . . ?
C2 O1 C3 110.40(11) . . ?
C1 N1 S1 122.31(9) . . ?
C4 N1 S1 121.29(9) . . ?
C4 N1 C1 112.79(11) . . ?
H10A C10 H10B 108.1 . . ?
C5 C10 H10A 109.6 . . ?
C5 C10 H10B 109.6 . . ?
C5 C10 C9 110.30(11) . . ?
C9 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H6A C6 H6B 108.4 . . ?
C5 C6 H6A 110.0 . . ?
C5 C6 H6B 110.0 . . ?
C5 C6 C7 108.28(11) . . ?
C7 C6 H6A 110.0 . . ?
C7 C6 H6B 110.0 . . ?
F1 C8 F2 104.20(10) . . ?
F1 C8 C7 109.75(11) . . ?
F1 C8 C9 109.48(11) . . ?
F2 C8 C7 109.13(11) . . ?
F2 C8 C9 109.13(11) . . ?
C7 C8 C9 114.63(11) . . ?
S1 C5 H5 107.0 . . ?
C10 C5 S1 110.66(9) . . ?
C10 C5 H5 107.0 . . ?
C6 C5 S1 113.61(9) . . ?
C6 C5 C10 111.24(11) . . ?
C6 C5 H5 107.0 . . ?
N1 C1 H1A 110.1 . . ?
N1 C1 H1B 110.1 . . ?
N1 C1 C2 108.24(11) . . ?
H1A C1 H1B 108.4 . . ?
C2 C1 H1A 110.1 . . ?
C2 C1 H1B 110.1 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C8 C7 C6 110.53(11) . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C10 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
C8 C9 C10 110.29(11) . . ?
C8 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
N1 C4 H4A 110.1 . . ?
N1 C4 H4B 110.1 . . ?
N1 C4 C3 107.81(12) . . ?
H4A C4 H4B 108.5 . . ?
C3 C4 H4A 110.1 . . ?
C3 C4 H4B 110.1 . . ?
O1 C2 C1 111.36(12) . . ?
O1 C2 H2A 109.4 . . ?
O1 C2 H2B 109.4 . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
O1 C3 C4 111.37(13) . . ?
O1 C3 H3A 109.4 . . ?
O1 C3 H3B 109.4 . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?

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 145.21(10) . . . . ?
S1 N1 C4 C3 -144.67(11) . . . . ?
F1 C8 C7 C6 -178.99(10) . . . . ?
F1 C8 C9 C10 176.78(10) . . . . ?
F2 C8 C7 C6 67.41(14) . . . . ?
F2 C8 C9 C10 -69.77(14) . . . . ?
O3 S1 N1 C1 -31.08(12) . . . . ?
O3 S1 N1 C4 171.90(10) . . . . ?
O3 S1 C5 C10 68.92(10) . . . . ?
O3 S1 C5 C6 -165.12(9) . . . . ?
O2 S1 N1 C1 -159.57(10) . . . . ?
O2 S1 N1 C4 43.40(12) . . . . ?
O2 S1 C5 C10 -162.52(9) . . . . ?
O2 S1 C5 C6 -36.55(11) . . . . ?
N1 S1 C5 C10 -46.26(11) . . . . ?
N1 S1 C5 C6 79.71(10) . . . . ?
N1 C1 C2 O1 56.61(15) . . . . ?
N1 C4 C3 O1 -57.60(17) . . . . ?
C5 S1 N1 C1 83.98(11) . . . . ?
C5 S1 N1 C4 -73.05(12) . . . . ?
C5 C10 C9 C8 -53.34(15) . . . . ?
C5 C6 C7 C8 56.82(14) . . . . ?
C1 N1 C4 C3 56.30(15) . . . . ?
C7 C6 C5 S1 174.24(9) . . . . ?
C7 C6 C5 C10 -60.10(14) . . . . ?
C7 C8 C9 C10 52.96(15) . . . . ?
C9 C10 C5 S1 -173.71(9) . . . . ?
C9 C10 C5 C6 59.00(14) . . . . ?
C9 C8 C7 C6 -55.32(15) . . . . ?
C4 N1 C1 C2 -56.00(15) . . . . ?
C2 O1 C3 C4 60.55(17) . . . . ?
C3 O1 C2 C1 -59.95(16) . . . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_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 1.223
_oxdiff_exptl_absorpt_empirical_full_min 0.855
####################################################################### 
# 
# 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_hpd170
_database_code_depnum_ccdc_archive 'CCDC 2042741'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman'
;University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2020-11-05 deposited with the CCDC.	2021-04-06 downloaded from the CCDC.
;
_audit_creation_date             2020-07-24
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H17 N O4 S'
_chemical_formula_sum            'C9 H17 N O4 S'
_chemical_formula_weight         235.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H S O N'
_chemical_oxdiff_usercomment     'VNY 184-12'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   18.4344(2)
_cell_length_b                   6.10100(10)
_cell_length_c                   9.77720(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.6050(10)
_cell_angle_gamma                90
_cell_volume                     1099.19(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8836
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.3360
_cell_measurement_theta_min      2.4030
_shelx_estimated_absorpt_T_max   0.771
_shelx_estimated_absorpt_T_min   0.507
_exptl_absorpt_coefficient_mu    2.613
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.397
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             504
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -4 2 0.0948
-4 -1 -6 0.1325
1 4 -1 0.0899
4 2 5 0.1257
-11 0 2 0.0656
12 0 -2 0.0154

_exptl_crystal_size_max          0.301
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_min          0.105
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
-1.0380 -3.7632 1.9134 0.0840 0.3567 0.9304
-3.5185 -0.8336 -5.8620 -0.2223 -0.9223 0.3162
1.3511 3.8402 -1.3948 -0.0643 -0.2752 -0.9592
3.7251 1.9465 5.1041 0.1901 0.7862 -0.5880
-11.4707 0.4760 1.8092 -0.9711 0.2336 0.0481
11.5867 0.2628 -1.7002 0.9452 -0.2277 -0.2338

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12863
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.521
_diffrn_reflns_theta_min         2.398
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -123.00 -29.00   0.50    0.05    --  -46.87 -15.00 113.00  188
  2  ω    -29.00  29.00   0.50    0.05    --  -46.87  15.00 -76.00  116
  3  ω     29.00 123.00   0.50    0.05    --   46.87  15.00 -76.00  188
  4  ω   -164.00 -71.00   0.50    0.05    --  -88.50 -15.00 113.00  186
  5  ω     89.00 178.00   0.50    0.05    --  106.69  15.00 -76.00  178
  6  ω   -120.00 -87.00   0.50    0.05    --  -46.87-125.00 120.00   66
  7  ω     83.00 120.00   0.50    0.05    --   46.87  57.00-180.00   74
  8  ω    -28.00  29.00   0.50    0.05    --   46.87 -15.00 113.00  114
  9  ω    -28.00  30.00   0.50    0.05    --   46.87 -19.00   0.00  116
 10  ω    -51.00 -16.00   0.50    0.05    --  -88.50  45.00-150.00   70
 11  ω    -51.00 -16.00   0.50    0.05    --  -88.50  45.00-120.00   70
 12  ω    -71.00 -15.00   0.50    0.05    --  -88.50  61.00 120.00  112
 13  ω    -51.00 -16.00   0.50    0.05    --  -88.50  45.00 -90.00   70
 14  ω    -71.00 -15.00   0.50    0.05    --  -88.50  61.00  60.00  112
 15  ω    -51.00 -16.00   0.50    0.05    --  -88.50  45.00 150.00   70
 16  ω   -160.00-100.00   0.50    0.05    --  -88.50 -94.00-120.00  120
 17  ω     34.00 111.00   0.50    0.05    --  106.69-125.00  30.00  154
 18  ω     34.00 105.00   0.50    0.05    --  106.69 -94.00  60.00  142
 19  ω     34.00  71.00   0.50    0.05    --  106.69 -61.00  30.00   74
 20  ω     34.00  71.00   0.50    0.05    --  106.69 -61.00 -90.00   74
 21  ω     34.00  71.00   0.50    0.05    --  106.69 -61.00 150.00   74
 22  ω     34.00  71.00   0.50    0.05    --  106.69 -61.00 -60.00   74
 23  ω     34.00  71.00   0.50    0.05    --  106.69 -61.00-150.00   74
 24  ω     34.00 101.00   0.50    0.05    --  106.69 -77.00 150.00  134
 25  ω     32.00 121.00   0.50    0.05    --   46.87  37.00  90.00  178
 26  ω     32.00 121.00   0.50    0.05    --   46.87  37.00-180.00  178
 27  ω     32.00 121.00   0.50    0.05    --   46.87  37.00 -90.00  178
 28  ω     34.00  96.00   0.50    0.05    --   46.87-125.00  60.00  124
 29  ω     32.00 109.00   0.50    0.05    --   46.87  37.00 -30.00  154
 30  ω     32.00 121.00   0.50    0.05    --   46.87  37.00   0.00  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0819829000
_diffrn_orient_matrix_UB_12      -0.0472551000
_diffrn_orient_matrix_UB_13      -0.0045591000
_diffrn_orient_matrix_UB_21      0.0037903000
_diffrn_orient_matrix_UB_22      -0.0158485000
_diffrn_orient_matrix_UB_23      0.1573095000
_diffrn_orient_matrix_UB_31      -0.0159123000
_diffrn_orient_matrix_UB_32      -0.2475282000
_diffrn_orient_matrix_UB_33      -0.0091910000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2062
_reflns_number_total             2219
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT n/a (Sheldrick, 2015)'
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0369
_refine_ls_restrained_S_all      1.094
_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)+(0.0580P)²+0.4372P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1034
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Others
 Fixed Sof: H1BC(0.65) H1BD(0.65) H1AA(0.35) H1AB(0.35) C4B(0.75) H4BA(0.75)
 H4BB(0.75) C3B(0.75) H3BA(0.75) H3BB(0.75) C2B(0.65) H2BA(0.65) H2BB(0.65)
 C2A(0.35) H2AA(0.35) H2AB(0.35) C4A(0.25) H4AA(0.25) H4AB(0.25) C3A(0.25)
 H3AA(0.25) H3AB(0.25)
3.a Ternary CH refined with riding coordinates:
 C5(H5)
3.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C9(H9A,H9B), C7(H7A,H7B), C8(H8A,H8B), C1(H1BC,H1BD), C1(H1AA,
 H1AB), C4B(H4BA,H4BB), C3B(H3BA,H3BB), C2B(H2BA,H2BB), C2A(H2AA,H2AB),
 C4A(H4AA,H4AB), C3A(H3AA,H3AB)
;
_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 0.25236(2) 0.33927(6) 0.32965(4) 0.02478(15) Uani 1 1 d . . . . .
O3 O 0.25695(6) 0.1044(2) 0.34008(12) 0.0329(3) Uani 1 1 d . . . . .
O2 O 0.23924(6) 0.46407(19) 0.45146(11) 0.0316(3) Uani 1 1 d . . . . .
O4 O 0.04989(7) 0.6184(2) 0.12966(12) 0.0364(3) Uani 1 1 d . . . . .
O1 O 0.45165(7) 0.5951(2) 0.14453(15) 0.0477(4) Uani 1 1 d . . . . .
N1 N 0.32765(7) 0.4300(2) 0.26770(13) 0.0275(3) Uani 1 1 d . . . . .
C5 C 0.18331(8) 0.4004(3) 0.20416(15) 0.0238(3) Uani 1 1 d . . . . .
H5 H 0.194344 0.318311 0.118695 0.029 Uiso 1 1 calc R U . . .
C6 C 0.18076(9) 0.6445(3) 0.17012(17) 0.0293(4) Uani 1 1 d . . . . .
H6A H 0.176101 0.730933 0.255128 0.035 Uiso 1 1 calc R U . . .
H6B H 0.226230 0.688776 0.126183 0.035 Uiso 1 1 calc R U . . .
C9 C 0.10984(9) 0.3212(3) 0.25445(17) 0.0296(4) Uani 1 1 d . . . . .
H9A H 0.110513 0.159810 0.265165 0.035 Uiso 1 1 calc R U . . .
H9B H 0.100210 0.387338 0.344598 0.035 Uiso 1 1 calc R U . . .
C7 C 0.11612(10) 0.6893(3) 0.07365(17) 0.0326(4) Uani 1 1 d . . . . .
H7A H 0.113244 0.848456 0.054540 0.039 Uiso 1 1 calc R U . . .
H7B H 0.123393 0.612619 -0.014149 0.039 Uiso 1 1 calc R U . . .
C8 C 0.05057(9) 0.3868(3) 0.15149(18) 0.0352(4) Uani 1 1 d . . . . .
H8A H 0.058513 0.311222 0.063564 0.042 Uiso 1 1 calc R U . . .
H8B H 0.002885 0.339850 0.185249 0.042 Uiso 1 1 calc R U . . .
C1 C 0.36244(13) 0.6301(3) 0.3179(2) 0.0505(5) Uani 1 1 d . . . . .
H1BC H 0.396375 0.594159 0.394926 0.061 Uiso 0.65 1 calc R U P A 2
H1BD H 0.325137 0.731301 0.352287 0.061 Uiso 0.65 1 calc R U P A 2
H1AA H 0.334319 0.756160 0.280988 0.061 Uiso 0.35 1 calc R U P B 1
H1AB H 0.358462 0.633182 0.418654 0.061 Uiso 0.35 1 calc R U P B 1
C4B C 0.37318(14) 0.2864(5) 0.1860(3) 0.0352(5) Uani 0.75 1 d . . P C 1
H4BA H 0.342868 0.170953 0.142027 0.042 Uiso 0.75 1 calc R U P C 1
H4BB H 0.410135 0.214359 0.246088 0.042 Uiso 0.75 1 calc R U P C 1
C3B C 0.40954(17) 0.4169(6) 0.0795(3) 0.0443(7) Uani 0.75 1 d . . P C 1
H3BA H 0.442190 0.321147 0.027424 0.053 Uiso 0.75 1 calc R U P C 1
H3BB H 0.372713 0.478882 0.014862 0.053 Uiso 0.75 1 calc R U P C 1
C2B C 0.40262(16) 0.7389(5) 0.2080(3) 0.0375(6) Uani 0.65 1 d . . P C 2
H2BA H 0.367555 0.795883 0.138144 0.045 Uiso 0.65 1 calc R U P C 2
H2BB H 0.429851 0.865178 0.246992 0.045 Uiso 0.65 1 calc R U P C 2
C2A C 0.4299(3) 0.6607(10) 0.2898(7) 0.0503(15) Uani 0.35 1 d . . P C 1
H2AA H 0.460298 0.576561 0.356337 0.060 Uiso 0.35 1 calc R U P C 1
H2AB H 0.441420 0.817864 0.303306 0.060 Uiso 0.35 1 calc R U P C 1
C4A C 0.3500(4) 0.3576(11) 0.1299(7) 0.0226(13) Uani 0.25 1 d . . P C 2
H4AA H 0.330207 0.456980 0.057978 0.027 Uiso 0.25 1 calc R U P C 2
H4AB H 0.332897 0.206713 0.110396 0.027 Uiso 0.25 1 calc R U P C 2
C3A C 0.4336(4) 0.3672(12) 0.1368(9) 0.0276(14) Uani 0.25 1 d . . P C 2
H3AA H 0.452770 0.288354 0.218592 0.033 Uiso 0.25 1 calc R U P C 2
H3AB H 0.454028 0.299944 0.054233 0.033 Uiso 0.25 1 calc R U P C 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.4386(12) . ?
S1 O2 1.4397(11) . ?
S1 N1 1.6270(13) . ?
S1 C5 1.7824(15) . ?
O4 C7 1.419(2) . ?
O4 C8 1.429(2) . ?
O1 C3B 1.470(3) . ?
O1 C2B 1.415(3) . ?
O1 C2A 1.539(7) . ?
O1 C3A 1.432(7) . ?
N1 C1 1.458(2) . ?
N1 C4B 1.465(3) . ?
N1 C4A 1.487(6) . ?
C5 H5 1.0000 . ?
C5 C6 1.526(2) . ?
C5 C9 1.532(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.524(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C8 1.518(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C1 H1BC 0.9900 . ?
C1 H1BD 0.9900 . ?
C1 H1AA 0.9900 . ?
C1 H1AB 0.9900 . ?
C1 C2B 1.480(3) . ?
C1 C2A 1.295(6) . ?
C4B H4BA 0.9900 . ?
C4B H4BB 0.9900 . ?
C4B C3B 1.485(4) . ?
C3B H3BA 0.9900 . ?
C3B H3BB 0.9900 . ?
C2B H2BA 0.9900 . ?
C2B H2BB 0.9900 . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C4A H4AA 0.9900 . ?
C4A H4AB 0.9900 . ?
C4A C3A 1.541(9) . ?
C3A H3AA 0.9900 . ?
C3A H3AB 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O2 118.62(7) . . ?
O3 S1 N1 108.43(7) . . ?
O3 S1 C5 107.26(7) . . ?
O2 S1 N1 107.03(7) . . ?
O2 S1 C5 109.00(7) . . ?
N1 S1 C5 105.82(7) . . ?
C7 O4 C8 110.78(13) . . ?
C3B O1 C2A 116.3(3) . . ?
C2B O1 C3A 118.3(3) . . ?
C1 N1 S1 122.11(12) . . ?
C1 N1 C4B 115.52(16) . . ?
C1 N1 C4A 115.1(3) . . ?
C4B N1 S1 120.47(14) . . ?
C4A N1 S1 119.8(3) . . ?
S1 C5 H5 108.2 . . ?
C6 C5 S1 111.80(11) . . ?
C6 C5 H5 108.2 . . ?
C6 C5 C9 110.84(13) . . ?
C9 C5 S1 109.49(10) . . ?
C9 C5 H5 108.2 . . ?
C5 C6 H6A 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.3 . . ?
C7 C6 C5 109.19(14) . . ?
C7 C6 H6A 109.8 . . ?
C7 C6 H6B 109.8 . . ?
C5 C9 H9A 109.8 . . ?
C5 C9 H9B 109.8 . . ?
H9A C9 H9B 108.3 . . ?
C8 C9 C5 109.27(13) . . ?
C8 C9 H9A 109.8 . . ?
C8 C9 H9B 109.8 . . ?
O4 C7 C6 111.89(13) . . ?
O4 C7 H7A 109.2 . . ?
O4 C7 H7B 109.2 . . ?
C6 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
O4 C8 C9 111.28(15) . . ?
O4 C8 H8A 109.4 . . ?
O4 C8 H8B 109.4 . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
N1 C1 H1BC 109.5 . . ?
N1 C1 H1BD 109.5 . . ?
N1 C1 H1AA 107.9 . . ?
N1 C1 H1AB 107.9 . . ?
N1 C1 C2B 110.83(19) . . ?
H1BC C1 H1BD 108.1 . . ?
H1AA C1 H1AB 107.2 . . ?
C2B C1 H1BC 109.5 . . ?
C2B C1 H1BD 109.5 . . ?
C2A C1 N1 117.7(3) . . ?
C2A C1 H1AA 107.9 . . ?
C2A C1 H1AB 107.9 . . ?
N1 C4B H4BA 109.7 . . ?
N1 C4B H4BB 109.7 . . ?
N1 C4B C3B 109.8(2) . . ?
H4BA C4B H4BB 108.2 . . ?
C3B C4B H4BA 109.7 . . ?
C3B C4B H4BB 109.7 . . ?
O1 C3B C4B 109.7(2) . . ?
O1 C3B H3BA 109.7 . . ?
O1 C3B H3BB 109.7 . . ?
C4B C3B H3BA 109.7 . . ?
C4B C3B H3BB 109.7 . . ?
H3BA C3B H3BB 108.2 . . ?
O1 C2B C1 112.3(2) . . ?
O1 C2B H2BA 109.1 . . ?
O1 C2B H2BB 109.1 . . ?
C1 C2B H2BA 109.1 . . ?
C1 C2B H2BB 109.1 . . ?
H2BA C2B H2BB 107.9 . . ?
O1 C2A H2AA 108.3 . . ?
O1 C2A H2AB 108.3 . . ?
C1 C2A O1 115.8(5) . . ?
C1 C2A H2AA 108.3 . . ?
C1 C2A H2AB 108.3 . . ?
H2AA C2A H2AB 107.4 . . ?
N1 C4A H4AA 110.8 . . ?
N1 C4A H4AB 110.8 . . ?
N1 C4A C3A 104.5(5) . . ?
H4AA C4A H4AB 108.9 . . ?
C3A C4A H4AA 110.8 . . ?
C3A C4A H4AB 110.8 . . ?
O1 C3A C4A 105.7(5) . . ?
O1 C3A H3AA 110.6 . . ?
O1 C3A H3AB 110.6 . . ?
C4A C3A H3AA 110.6 . . ?
C4A C3A H3AB 110.6 . . ?
H3AA C3A H3AB 108.7 . . ?

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 C2B -149.73(17) . . . . ?
S1 N1 C1 C2A 162.6(4) . . . . ?
S1 N1 C4B C3B 146.75(18) . . . . ?
S1 N1 C4A C3A -150.9(4) . . . . ?
S1 C5 C6 C7 -174.35(11) . . . . ?
S1 C5 C9 C8 176.34(11) . . . . ?
O3 S1 N1 C1 -140.22(16) . . . . ?
O3 S1 N1 C4B 23.39(19) . . . . ?
O3 S1 N1 C4A 60.5(3) . . . . ?
O3 S1 C5 C6 -172.11(10) . . . . ?
O3 S1 C5 C9 64.66(12) . . . . ?
O2 S1 N1 C1 -11.17(18) . . . . ?
O2 S1 N1 C4B 152.44(17) . . . . ?
O2 S1 N1 C4A -170.5(3) . . . . ?
O2 S1 C5 C6 58.30(12) . . . . ?
O2 S1 C5 C9 -64.93(13) . . . . ?
N1 S1 C5 C6 -56.50(12) . . . . ?
N1 S1 C5 C9 -179.73(11) . . . . ?
N1 C1 C2B O1 -52.9(3) . . . . ?
N1 C1 C2A O1 40.4(7) . . . . ?
N1 C4B C3B O1 56.6(3) . . . . ?
N1 C4A C3A O1 -69.0(6) . . . . ?
C5 S1 N1 C1 104.97(17) . . . . ?
C5 S1 N1 C4B -91.42(18) . . . . ?
C5 S1 N1 C4A -54.3(3) . . . . ?
C5 C6 C7 O4 56.62(18) . . . . ?
C5 C9 C8 O4 -57.26(18) . . . . ?
C6 C5 C9 C8 52.55(18) . . . . ?
C9 C5 C6 C7 -51.89(17) . . . . ?
C7 O4 C8 C9 62.43(18) . . . . ?
C8 O4 C7 C6 -62.14(18) . . . . ?
C1 N1 C4B C3B -48.6(3) . . . . ?
C1 N1 C4A C3A 48.4(6) . . . . ?
C4B N1 C1 C2A -1.8(5) . . . . ?
C3B O1 C2A C1 -29.0(7) . . . . ?
C2B O1 C3A C4A 29.8(7) . . . . ?
C2A O1 C3B C4B -20.4(4) . . . . ?
C4A N1 C1 C2B 10.5(4) . . . . ?
C3A O1 C2B C1 31.0(5) . . . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.305
_oxdiff_exptl_absorpt_empirical_full_min 0.751
####################################################################### 
# 
# 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_hpd197
_database_code_depnum_ccdc_archive 'CCDC 2042743'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman'
;University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2020-11-05 deposited with the CCDC.	2021-04-06 downloaded from the CCDC.
;
_audit_creation_date             2020-08-11
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H25 N O2 S'
_chemical_formula_sum            'C14 H25 N O2 S'
_chemical_formula_weight         271.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S'
_chemical_oxdiff_usercomment     VNY-199-3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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/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                   6.47310(10)
_cell_length_b                   19.8101(2)
_cell_length_c                   11.04280(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.9930(10)
_cell_angle_gamma                90
_cell_volume                     1410.68(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9905
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      75.6390
_cell_measurement_theta_min      4.4600
_shelx_estimated_absorpt_T_max   0.898
_shelx_estimated_absorpt_T_min   0.625
_exptl_absorpt_coefficient_mu    1.992
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.676
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 0 -1 0.1107
0 10 4 0.0499
4 -5 -1 0.1074
0 -10 -4 0.0540
-1 -7 6 0.0075
0 7 -6 0.0302

_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.055
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
-4.1163 -0.1074 -0.8182 0.0235 0.0904 0.9956
0.0805 10.4929 4.1149 0.2269 0.9455 -0.2336
3.8125 -5.2362 -1.3270 -0.1374 -0.5655 -0.8132
-0.1558 -10.4658 -4.1186 -0.2258 -0.9412 0.2512
-0.6447 -7.2961 5.8717 0.9723 -0.2337 -0.0089
0.1369 7.0950 -5.9699 -0.9637 0.2315 0.1329

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16425
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.467
_diffrn_reflns_theta_min         4.464
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -24.00   0.50    0.05    --  -46.87 147.00 -43.00  156
  2  ω   -120.00 -74.00   0.50    0.05    --  -46.87-124.00  71.00   92
  3  ω   -120.00 -58.00   0.50    0.05    --  -46.87-147.00 -93.00  124
  4  ω     46.00 108.00   0.50    0.05    --   46.87-147.00 -93.00  124
  5  ω     34.00  95.00   0.50    0.05    --   46.87-124.00  71.00  122
  6  ω   -101.00 -24.00   0.50    0.11    --  -88.50 147.00 -43.00  154
  7  ω   -160.00 -74.00   0.50    0.11    --  -88.50-124.00  71.00  172
  8  ω     46.00 128.00   0.50    0.11    --  106.69-147.00 -93.00  164
  9  ω     34.00 111.00   0.50    0.11    --  106.69-124.00  71.00  154
 10  ω   -120.00 -83.00   0.50    0.05    --  -46.87 -57.00  60.00   74
 11  ω   -120.00 -83.00   0.50    0.05    --  -46.87 -57.00 -30.00   74
 12  ω     83.00 120.00   0.50    0.05    --   46.87  57.00-180.00   74
 13  ω     83.00 120.00   0.50    0.05    --   46.87  57.00 -30.00   74
 14  ω    -51.00 -16.00   0.50    0.11    --  -88.50  45.00 -30.00   70
 15  ω    -51.00 -16.00   0.50    0.11    --  -88.50  45.00  30.00   70
 16  ω    -51.00 -16.00   0.50    0.11    --  -88.50  45.00   0.00   70
 17  ω   -151.00 -58.00   0.50    0.11    --  -88.50-147.00 -93.00  186
 18  ω     34.00 105.00   0.50    0.11    --  106.69 -94.00-120.00  142
 19  ω     34.00 105.00   0.50    0.11    --  106.69 -94.00 -90.00  142
 20  ω     89.00 178.00   0.50    0.11    --  106.69  15.00  90.00  178
 21  ω     89.00 178.00   0.50    0.11    --  106.69  15.00 150.00  178
 22  ω     34.00 101.00   0.50    0.11    --  106.69 -77.00  60.00  134
 23  ω     34.00  71.00   0.50    0.11    --  106.69 -61.00  60.00   74
 24  ω     34.00  71.00   0.50    0.11    --  106.69 -61.00  90.00   74
 25  ω     80.00 168.00   0.50    0.11    --  106.69 147.00 -43.00  176
 26  ω   -120.00 -83.00   0.50    0.05    --  -46.87 -57.00 -90.00   74
 27  ω     32.00  77.00   0.50    0.05    --   46.87  37.00 -60.00   90
 28  ω     32.00 121.00   0.50    0.05    --   46.87  37.00  90.00  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0302974000
_diffrn_orient_matrix_UB_12      -0.0280873000
_diffrn_orient_matrix_UB_13      0.1273560000
_diffrn_orient_matrix_UB_21      -0.0330355000
_diffrn_orient_matrix_UB_22      0.0722086000
_diffrn_orient_matrix_UB_23      0.0462883000
_diffrn_orient_matrix_UB_31      -0.2346589000
_diffrn_orient_matrix_UB_32      -0.0065628000
_diffrn_orient_matrix_UB_33      -0.0354373000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2706
_reflns_number_total             2875
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT n/a (Sheldrick, 2015)'
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2875
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0321
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0459P)²+0.5650P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0871
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C3(H3), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C7(H7A,H7B), C6(H6A,H6B), C10(H10A,H10B), C4(H4A,H4B), C9(H9A,H9B)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.45771(4) 0.57993(2) 0.34892(3) 0.01393(11) Uani 1 1 d . . . . .
O2 O 0.38407(13) 0.60168(5) 0.22841(8) 0.0184(2) Uani 1 1 d . . . . .
O1 O 0.31058(13) 0.54821(5) 0.42273(8) 0.0185(2) Uani 1 1 d . . . . .
N1 N 0.65400(16) 0.53003(6) 0.34067(10) 0.0164(2) Uani 1 1 d . . . . .
C1 C 0.55504(17) 0.65278(6) 0.43387(10) 0.0133(2) Uani 1 1 d . . . . .
C8 C 0.69064(19) 0.69554(6) 0.63869(11) 0.0161(3) Uani 1 1 d . . . . .
H8 H 0.733573 0.682467 0.724677 0.019 Uiso 1 1 calc R U . . .
C2 C 0.74001(19) 0.68452(6) 0.37696(11) 0.0159(3) Uani 1 1 d . . . . .
H2A H 0.699491 0.696880 0.291314 0.019 Uiso 1 1 calc R U . . .
H2B H 0.855749 0.651785 0.378418 0.019 Uiso 1 1 calc R U . . .
C7 C 0.62080(19) 0.63235(6) 0.56576(11) 0.0161(3) Uani 1 1 d . . . . .
H7A H 0.502902 0.610830 0.602255 0.019 Uiso 1 1 calc R U . . .
H7B H 0.736029 0.599401 0.567625 0.019 Uiso 1 1 calc R U . . .
C11 C 0.73114(19) 0.50202(6) 0.22657(11) 0.0175(3) Uani 1 1 d . . . . .
C3 C 0.80908(19) 0.74793(7) 0.45026(11) 0.0175(3) Uani 1 1 d . . . . .
H3 H 0.929196 0.769181 0.413639 0.021 Uiso 1 1 calc R U . . .
C6 C 0.37449(19) 0.70348(6) 0.43062(11) 0.0171(3) Uani 1 1 d . . . . .
H6A H 0.331701 0.716387 0.345512 0.020 Uiso 1 1 calc R U . . .
H6B H 0.254126 0.682581 0.465602 0.020 Uiso 1 1 calc R U . . .
C5 C 0.4449(2) 0.76635(7) 0.50437(12) 0.0197(3) Uani 1 1 d . . . . .
H5 H 0.328165 0.799486 0.502800 0.024 Uiso 1 1 calc R U . . .
C10 C 0.87453(19) 0.72836(7) 0.58265(11) 0.0174(3) Uani 1 1 d . . . . .
H10A H 0.992289 0.696349 0.585406 0.021 Uiso 1 1 calc R U . . .
H10B H 0.919905 0.769066 0.629715 0.021 Uiso 1 1 calc R U . . .
C4 C 0.6301(2) 0.79868(6) 0.44826(12) 0.0211(3) Uani 1 1 d . . . . .
H4A H 0.588331 0.812427 0.363462 0.025 Uiso 1 1 calc R U . . .
H4B H 0.675620 0.839494 0.494970 0.025 Uiso 1 1 calc R U . . .
C14 C 0.9101(2) 0.45559(7) 0.27176(13) 0.0235(3) Uani 1 1 d . . . . .
H14A H 1.015198 0.481685 0.320907 0.035 Uiso 1 1 calc R U . . .
H14B H 0.972049 0.435898 0.201998 0.035 Uiso 1 1 calc R U . . .
H14C H 0.857732 0.419425 0.321355 0.035 Uiso 1 1 calc R U . . .
C12 C 0.5619(2) 0.46152(7) 0.15288(12) 0.0207(3) Uani 1 1 d . . . . .
H12A H 0.513476 0.425059 0.203303 0.031 Uiso 1 1 calc R U . . .
H12B H 0.618579 0.442227 0.081047 0.031 Uiso 1 1 calc R U . . .
H12C H 0.445570 0.491373 0.127193 0.031 Uiso 1 1 calc R U . . .
C9 C 0.5103(2) 0.74594(7) 0.63649(12) 0.0195(3) Uani 1 1 d . . . . .
H9A H 0.553769 0.786447 0.684667 0.023 Uiso 1 1 calc R U . . .
H9B H 0.391544 0.725073 0.673178 0.023 Uiso 1 1 calc R U . . .
C13 C 0.8136(2) 0.55851(7) 0.14962(13) 0.0234(3) Uani 1 1 d . . . . .
H13A H 0.701343 0.590245 0.125584 0.035 Uiso 1 1 calc R U . . .
H13B H 0.866571 0.539113 0.076757 0.035 Uiso 1 1 calc R U . . .
H13C H 0.925825 0.582366 0.197186 0.035 Uiso 1 1 calc R U . . .
H1 H 0.667(3) 0.5043(9) 0.4023(16) 0.028 Uiso 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4400(9) . ?
S1 O1 1.4496(9) . ?
S1 N1 1.6187(11) . ?
S1 C1 1.8047(12) . ?
N1 C11 1.5014(16) . ?
N1 H1 0.848(18) . ?
C1 C2 1.5346(16) . ?
C1 C7 1.5357(16) . ?
C1 C6 1.5390(16) . ?
C8 H8 1.0000 . ?
C8 C7 1.5353(17) . ?
C8 C10 1.5332(17) . ?
C8 C9 1.5346(17) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5393(17) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C11 C14 1.5284(18) . ?
C11 C12 1.5332(17) . ?
C11 C13 1.5292(18) . ?
C3 H3 1.0000 . ?
C3 C10 1.5360(17) . ?
C3 C4 1.5328(18) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C5 1.5353(18) . ?
C5 H5 1.0000 . ?
C5 C4 1.5363(19) . ?
C5 C9 1.5375(18) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 117.94(5) . . ?
O2 S1 N1 109.21(5) . . ?
O2 S1 C1 108.28(5) . . ?
O1 S1 N1 108.92(6) . . ?
O1 S1 C1 105.73(5) . . ?
N1 S1 C1 106.11(5) . . ?
S1 N1 H1 110.1(12) . . ?
C11 N1 S1 126.37(9) . . ?
C11 N1 H1 115.8(12) . . ?
C2 C1 S1 111.37(8) . . ?
C2 C1 C7 109.55(9) . . ?
C2 C1 C6 109.94(10) . . ?
C7 C1 S1 109.73(8) . . ?
C7 C1 C6 109.96(10) . . ?
C6 C1 S1 106.25(8) . . ?
C7 C8 H8 109.4 . . ?
C10 C8 H8 109.4 . . ?
C10 C8 C7 109.72(10) . . ?
C10 C8 C9 109.51(10) . . ?
C9 C8 H8 109.4 . . ?
C9 C8 C7 109.47(10) . . ?
C1 C2 H2A 110.0 . . ?
C1 C2 H2B 110.0 . . ?
C1 C2 C3 108.68(10) . . ?
H2A C2 H2B 108.3 . . ?
C3 C2 H2A 110.0 . . ?
C3 C2 H2B 110.0 . . ?
C1 C7 H7A 109.9 . . ?
C1 C7 H7B 109.9 . . ?
C8 C7 C1 109.10(10) . . ?
C8 C7 H7A 109.9 . . ?
C8 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
N1 C11 C14 104.26(10) . . ?
N1 C11 C12 111.37(10) . . ?
N1 C11 C13 110.71(10) . . ?
C14 C11 C12 110.15(11) . . ?
C14 C11 C13 109.30(11) . . ?
C13 C11 C12 110.85(11) . . ?
C2 C3 H3 109.4 . . ?
C10 C3 C2 109.75(10) . . ?
C10 C3 H3 109.4 . . ?
C4 C3 C2 110.06(10) . . ?
C4 C3 H3 109.4 . . ?
C4 C3 C10 108.95(10) . . ?
C1 C6 H6A 109.9 . . ?
C1 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
C5 C6 C1 109.10(10) . . ?
C5 C6 H6A 109.9 . . ?
C5 C6 H6B 109.9 . . ?
C6 C5 H5 109.5 . . ?
C6 C5 C4 109.29(10) . . ?
C6 C5 C9 109.54(11) . . ?
C4 C5 H5 109.5 . . ?
C4 C5 C9 109.41(10) . . ?
C9 C5 H5 109.5 . . ?
C8 C10 C3 109.37(10) . . ?
C8 C10 H10A 109.8 . . ?
C8 C10 H10B 109.8 . . ?
C3 C10 H10A 109.8 . . ?
C3 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
C3 C4 C5 109.64(10) . . ?
C3 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
C5 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C9 C5 109.41(10) . . ?
C8 C9 H9A 109.8 . . ?
C8 C9 H9B 109.8 . . ?
C5 C9 H9A 109.8 . . ?
C5 C9 H9B 109.8 . . ?
H9A C9 H9B 108.2 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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 C11 C14 -177.01(9) . . . . ?
S1 N1 C11 C12 -58.25(14) . . . . ?
S1 N1 C11 C13 65.57(14) . . . . ?
S1 C1 C2 C3 177.56(8) . . . . ?
S1 C1 C7 C8 -176.57(8) . . . . ?
S1 C1 C6 C5 178.54(8) . . . . ?
O2 S1 N1 C11 -8.22(12) . . . . ?
O2 S1 C1 C2 -62.52(9) . . . . ?
O2 S1 C1 C7 176.01(8) . . . . ?
O2 S1 C1 C6 57.18(9) . . . . ?
O1 S1 N1 C11 121.86(10) . . . . ?
O1 S1 C1 C2 170.20(8) . . . . ?
O1 S1 C1 C7 48.73(9) . . . . ?
O1 S1 C1 C6 -70.10(9) . . . . ?
N1 S1 C1 C2 54.61(10) . . . . ?
N1 S1 C1 C7 -66.86(9) . . . . ?
N1 S1 C1 C6 174.31(8) . . . . ?
C1 S1 N1 C11 -124.72(10) . . . . ?
C1 C2 C3 C10 60.35(12) . . . . ?
C1 C2 C3 C4 -59.54(13) . . . . ?
C1 C6 C5 C4 60.13(13) . . . . ?
C1 C6 C5 C9 -59.72(13) . . . . ?
C2 C1 C7 C8 60.87(12) . . . . ?
C2 C1 C6 C5 -60.83(13) . . . . ?
C2 C3 C10 C8 -59.85(13) . . . . ?
C2 C3 C4 C5 59.83(13) . . . . ?
C7 C1 C2 C3 -60.87(13) . . . . ?
C7 C1 C6 C5 59.87(13) . . . . ?
C7 C8 C10 C3 59.58(13) . . . . ?
C7 C8 C9 C5 -60.47(13) . . . . ?
C6 C1 C2 C3 60.07(12) . . . . ?
C6 C1 C7 C8 -60.06(12) . . . . ?
C6 C5 C4 C3 -59.86(13) . . . . ?
C6 C5 C9 C8 60.32(13) . . . . ?
C10 C8 C7 C1 -60.04(13) . . . . ?
C10 C8 C9 C5 59.87(13) . . . . ?
C10 C3 C4 C5 -60.55(13) . . . . ?
C4 C3 C10 C8 60.73(13) . . . . ?
C4 C5 C9 C8 -59.47(13) . . . . ?
C9 C8 C7 C1 60.16(12) . . . . ?
C9 C8 C10 C3 -60.61(13) . . . . ?
C9 C5 C4 C3 60.08(13) . . . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_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 1.215
_oxdiff_exptl_absorpt_empirical_full_min 0.871
####################################################################### 
# 
# 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_hpd191
_database_code_depnum_ccdc_archive 'CCDC 2042744'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman'
;University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2020-11-05 deposited with the CCDC.	2021-04-06 downloaded from the CCDC.
;
_audit_creation_date             2020-08-10
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H17 N O3 S'
_chemical_formula_sum            'C12 H17 N O3 S'
_chemical_formula_weight         255.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H S O N'
_chemical_oxdiff_usercomment     203-A3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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/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                   5.4965(2)
_cell_length_b                   24.4849(12)
_cell_length_c                   9.7713(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.544(4)
_cell_angle_gamma                90
_cell_volume                     1266.94(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4354
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.8620
_cell_measurement_theta_min      5.0090
_shelx_estimated_absorpt_T_max   0.907
_shelx_estimated_absorpt_T_min   0.695
_exptl_absorpt_coefficient_mu    2.256
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.533
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 4 -5 0.0690
-4 2 2 0.0820
-3 0 5 0.0861
0 -4 6 0.0712
4 -3 -2 0.0594
0 -16 1 0.0191
-1 16 1 0.0037

_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.044
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
-0.8209 4.1010 -5.3417 -0.1551 -0.6390 0.7534
-3.5213 2.4936 1.9043 -0.2062 -0.8613 -0.4643
-3.0946 0.4662 4.5094 -0.1288 -0.5422 -0.8303
0.1727 -3.7370 5.8484 0.1200 0.4923 -0.8621
3.5165 -2.6799 -1.5900 0.2117 0.8838 0.4172
0.3960 -15.6334 0.6955 -0.7765 0.5958 -0.2049
-0.7331 15.5547 0.5212 0.7931 -0.6090 0.0090

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11078
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.662
_diffrn_reflns_theta_min         3.610
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -31.00  28.00   0.50    0.15    --  -45.87  39.00 125.00  118
  2  ω   -119.00 -32.00   0.50    0.15    --  -45.87 -39.00 -28.00  174
  3  ω     16.00  45.00   0.50    0.15    --   45.87 -39.00 -28.00   58
  4  ω   -111.00 -75.00   0.50    0.60    --  -88.50 -39.00 -28.00   72
  5  ω   -162.00-136.00   0.50    0.60    --  -88.50 -39.00 -28.00   52
  6  ω    -44.00 -19.00   0.50    0.60    --  -88.50  39.00 125.00   50
  7  ω     93.00 173.00   0.50    0.60    --  106.69  39.00 125.00  160
  8  ω   -117.00 -88.00   0.50    0.15    --  -45.87-125.00 120.00   58
  9  ω     34.00  82.00   0.50    0.15    --   45.87-125.00   0.00   96
 10  ω     83.00 117.00   0.50    0.15    --   45.87  57.00  60.00   68
 11  ω     56.00  83.00   0.50    0.15    --   45.87  39.00 125.00   54
 12  ω    -46.00 -16.00   0.50    0.60    --  -88.50  45.00  60.00   60
 13  ω   -125.00-100.00   0.50    0.60    --  -88.50 -94.00  90.00   50
 14  ω    -64.00 -16.00   0.50    0.60    --  -88.50  57.00 -79.96   96
 15  ω    -47.00 -16.00   0.50    0.60    --  -88.50  45.00 -60.00   62
 16  ω    -49.00 -17.00   0.50    0.60    --  -88.50  45.00-150.00   64
 17  ω    -42.00 -17.00   0.50    0.60    --  -88.50  45.00-180.00   50
 18  ω     34.00  66.00   0.50    0.60    --  106.69 -61.00 120.00   64
 19  ω     57.00 107.00   0.50    0.60    --  106.69-102.00 119.40  100
 20  ω     35.00  66.00   0.50    0.60    --  106.69-125.00  60.00   62
 21  ω     77.00 111.00   0.50    0.60    --  106.69-125.00  60.00   68
 22  ω    112.00 162.00   0.50    0.60    --  106.69  15.00  60.00  100
 23  ω     38.00  65.00   0.50    0.60    --  106.69 -60.00-173.67   54
 24  ω     41.00  69.00   0.50    0.60    --  106.69 -61.00-120.00   56
 25  ω     76.00 105.00   0.50    0.60    --  106.69-125.00-150.00   58
 26  ω     36.00  75.00   0.50    0.60    --  106.69-125.00-150.00   78
 27  ω     72.00 105.00   0.50    0.60    --  106.69 -94.00-150.00   66
 28  ω     46.00  74.00   0.50    0.60    --  106.69-114.00   3.26   56
 29  ω     81.00 109.00   0.50    0.60    --  106.69-114.00   3.26   56
 30  ω     45.00  71.00   0.50    0.60    --  106.69 -61.00-150.00   52
 31  ω     56.00  83.00   0.50    0.60    --  106.69 -94.00  90.00   54
 32  ω     89.00 177.00   0.50    0.60    --  106.69  15.00-120.00  176
 33  ω     43.00  70.00   0.50    0.60    --  106.69 -77.00  60.00   54
 34  ω     40.00 106.00   0.50    0.60    --  106.69-102.00  73.52  132
 35  ω    -58.00 -32.00   0.50    0.15    --  -45.87 -38.00 -27.00   52
 36  ω   -123.00 -97.00   0.50    0.60    --  -88.50-125.00  60.00   52
 37  ω   -156.00-129.00   0.50    0.60    --  -88.50 -94.00 -60.00   54
 38  ω     56.00 101.00   0.50    0.60    --  106.69 -77.00-120.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1257887000
_diffrn_orient_matrix_UB_12      0.0551735000
_diffrn_orient_matrix_UB_13      0.0520578000
_diffrn_orient_matrix_UB_21      0.2554377000
_diffrn_orient_matrix_UB_22      -0.0290586000
_diffrn_orient_matrix_UB_23      0.0580662000
_diffrn_orient_matrix_UB_31      0.0598348000
_diffrn_orient_matrix_UB_32      0.0082206000
_diffrn_orient_matrix_UB_33      -0.1439234000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2308
_reflns_number_total             2554
_reflns_odcompleteness_completeness 99.06
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT n/a (Sheldrick, 2015)'
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2554
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0486
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0350P)²+2.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1217
_refine_ls_wR_factor_ref         0.1239
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C4(H4A,H4B), C1(H1A,H1B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), C12(H12), C10(H10), C9(H9)
;
_atom_sites_solution_hydrogens   mixed
_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 0.65368(10) 0.20640(2) 0.52936(6) 0.02101(17) Uani 1 1 d . . . . .
O3 O 0.5042(3) 0.21857(7) 0.38804(17) 0.0275(4) Uani 1 1 d . . . . .
O2 O 0.9130(3) 0.19147(7) 0.54899(19) 0.0297(4) Uani 1 1 d . . . . .
O1 O 0.4706(4) 0.04368(8) 0.6947(2) 0.0358(4) Uani 1 1 d . . . . .
N1 N 0.6530(4) 0.25937(8) 0.6254(2) 0.0254(4) Uani 1 1 d . . . . .
C8 C 0.6232(4) 0.37556(10) 0.5841(2) 0.0239(5) Uani 1 1 d . . . . .
H8 H 0.724635 0.355717 0.536464 0.029 Uiso 1 1 calc R U . . .
C7 C 0.4498(4) 0.34798(10) 0.6400(2) 0.0217(5) Uani 1 1 d . . . . .
C11 C 0.3239(5) 0.43419(10) 0.7193(2) 0.0268(5) Uani 1 1 d . . . . .
H11 H 0.219833 0.454248 0.764842 0.032 Uiso 1 1 calc R U . . .
C2 C 0.4479(5) 0.10407(10) 0.4938(3) 0.0257(5) Uani 1 1 d . . . . .
H2A H 0.338094 0.114987 0.399944 0.031 Uiso 1 1 calc R U . . .
H2B H 0.610016 0.090650 0.480529 0.031 Uiso 1 1 calc R U . . .
C3 C 0.4948(4) 0.15284(10) 0.5946(2) 0.0217(5) Uani 1 1 d . . . . .
H3 H 0.326929 0.167102 0.599699 0.026 Uiso 1 1 calc R U . . .
C12 C 0.3000(4) 0.37800(10) 0.7073(2) 0.0237(5) Uani 1 1 d . . . . .
H12 H 0.180316 0.359721 0.745343 0.028 Uiso 1 1 calc R U . . .
C10 C 0.4992(5) 0.46130(10) 0.6651(3) 0.0280(5) Uani 1 1 d . . . . .
H10 H 0.517029 0.499821 0.674194 0.034 Uiso 1 1 calc R U . . .
C9 C 0.6484(5) 0.43172(11) 0.5974(3) 0.0274(5) Uani 1 1 d . . . . .
H9 H 0.768568 0.450108 0.559971 0.033 Uiso 1 1 calc R U . . .
C6 C 0.4168(5) 0.28697(10) 0.6283(3) 0.0266(5) Uani 1 1 d . . . . .
H6A H 0.360298 0.273350 0.710157 0.032 Uiso 1 1 calc R U . . .
H6B H 0.284227 0.278045 0.540509 0.032 Uiso 1 1 calc R U . . .
C4 C 0.6414(5) 0.13545(11) 0.7441(2) 0.0295(5) Uani 1 1 d . . . . .
H4A H 0.814412 0.124165 0.744264 0.035 Uiso 1 1 calc R U . . .
H4B H 0.654247 0.166509 0.810550 0.035 Uiso 1 1 calc R U . . .
C1 C 0.3210(5) 0.05925(11) 0.5578(3) 0.0324(6) Uani 1 1 d . . . . .
H1A H 0.154560 0.072345 0.565203 0.039 Uiso 1 1 calc R U . . .
H1B H 0.292203 0.027021 0.494294 0.039 Uiso 1 1 calc R U . . .
C5 C 0.5048(5) 0.08809(12) 0.7917(3) 0.0354(6) Uani 1 1 d . . . . .
H5A H 0.603500 0.075620 0.886746 0.042 Uiso 1 1 calc R U . . .
H5B H 0.337946 0.100665 0.799683 0.042 Uiso 1 1 calc R U . . .
H1 H 0.769(6) 0.2599(14) 0.706(4) 0.042 Uiso 1 1 d . 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 O3 1.4361(16) . ?
S1 O2 1.4340(17) . ?
S1 N1 1.602(2) . ?
S1 C3 1.786(2) . ?
O1 C1 1.422(3) . ?
O1 C5 1.422(3) . ?
N1 C6 1.470(3) . ?
N1 H1 0.87(4) . ?
C8 H8 0.9500 . ?
C8 C7 1.394(3) . ?
C8 C9 1.385(4) . ?
C7 C12 1.393(3) . ?
C7 C6 1.505(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(3) . ?
C11 C10 1.387(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.526(3) . ?
C2 C1 1.522(3) . ?
C3 H3 1.0000 . ?
C3 C4 1.528(3) . ?
C12 H12 0.9500 . ?
C10 H10 0.9500 . ?
C10 C9 1.387(4) . ?
C9 H9 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.520(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 N1 107.76(11) . . ?
O3 S1 C3 106.69(10) . . ?
O2 S1 O3 118.27(11) . . ?
O2 S1 N1 106.65(11) . . ?
O2 S1 C3 109.20(11) . . ?
N1 S1 C3 107.89(11) . . ?
C5 O1 C1 111.2(2) . . ?
S1 N1 H1 115(2) . . ?
C6 N1 S1 121.61(16) . . ?
C6 N1 H1 114(2) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C9 C8 C7 120.4(2) . . ?
C8 C7 C6 122.2(2) . . ?
C12 C7 C8 118.8(2) . . ?
C12 C7 C6 119.0(2) . . ?
C12 C11 H11 119.9 . . ?
C12 C11 C10 120.2(2) . . ?
C10 C11 H11 119.9 . . ?
H2A C2 H2B 108.4 . . ?
C3 C2 H2A 110.0 . . ?
C3 C2 H2B 110.0 . . ?
C1 C2 H2A 110.0 . . ?
C1 C2 H2B 110.0 . . ?
C1 C2 C3 108.4(2) . . ?
S1 C3 H3 107.9 . . ?
C2 C3 S1 111.00(16) . . ?
C2 C3 H3 107.9 . . ?
C2 C3 C4 110.7(2) . . ?
C4 C3 S1 111.28(16) . . ?
C4 C3 H3 107.9 . . ?
C7 C12 H12 119.7 . . ?
C11 C12 C7 120.7(2) . . ?
C11 C12 H12 119.7 . . ?
C11 C10 H10 120.3 . . ?
C11 C10 C9 119.5(2) . . ?
C9 C10 H10 120.3 . . ?
C8 C9 C10 120.4(2) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
N1 C6 C7 111.6(2) . . ?
N1 C6 H6A 109.3 . . ?
N1 C6 H6B 109.3 . . ?
C7 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C3 C4 H4A 109.9 . . ?
C3 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
C5 C4 C3 109.1(2) . . ?
C5 C4 H4A 109.9 . . ?
C5 C4 H4B 109.9 . . ?
O1 C1 C2 111.5(2) . . ?
O1 C1 H1A 109.3 . . ?
O1 C1 H1B 109.3 . . ?
C2 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
O1 C5 C4 111.6(2) . . ?
O1 C5 H5A 109.3 . . ?
O1 C5 H5B 109.3 . . ?
C4 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?

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 C6 C7 -143.41(18) . . . . ?
S1 C3 C4 C5 -177.33(18) . . . . ?
O3 S1 N1 C6 50.4(2) . . . . ?
O3 S1 C3 C2 54.79(18) . . . . ?
O3 S1 C3 C4 178.60(16) . . . . ?
O2 S1 N1 C6 178.32(18) . . . . ?
O2 S1 C3 C2 -74.11(18) . . . . ?
O2 S1 C3 C4 49.7(2) . . . . ?
N1 S1 C3 C2 170.35(16) . . . . ?
N1 S1 C3 C4 -65.85(19) . . . . ?
C8 C7 C12 C11 -0.4(3) . . . . ?
C8 C7 C6 N1 30.1(3) . . . . ?
C7 C8 C9 C10 -0.8(3) . . . . ?
C11 C10 C9 C8 -0.1(4) . . . . ?
C2 C3 C4 C5 -53.4(3) . . . . ?
C3 S1 N1 C6 -64.5(2) . . . . ?
C3 C2 C1 O1 -58.0(3) . . . . ?
C3 C4 C5 O1 56.4(3) . . . . ?
C12 C7 C6 N1 -150.8(2) . . . . ?
C12 C11 C10 C9 0.7(4) . . . . ?
C10 C11 C12 C7 -0.4(4) . . . . ?
C9 C8 C7 C12 1.1(3) . . . . ?
C9 C8 C7 C6 -179.8(2) . . . . ?
C6 C7 C12 C11 -179.6(2) . . . . ?
C1 O1 C5 C4 -61.3(3) . . . . ?
C1 C2 C3 S1 178.01(16) . . . . ?
C1 C2 C3 C4 53.9(3) . . . . ?
C5 O1 C1 C2 62.3(3) . . . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_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 1.296
_oxdiff_exptl_absorpt_empirical_full_min 0.775
####################################################################### 
# 
# 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_hpd223b
_database_code_depnum_ccdc_archive 'CCDC 2042746'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman'
;University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2020-11-05 deposited with the CCDC.	2021-04-06 downloaded from the CCDC.
;
_audit_creation_date             2020-09-29
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H11 N3 O3 S2'
_chemical_formula_sum            'C9 H11 N3 O3 S2'
_chemical_formula_weight         273.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S'
_chemical_oxdiff_usercomment     thiophene
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.49570(10)
_cell_length_b                   5.8614(2)
_cell_length_c                   18.6487(6)
_cell_angle_alpha                83.542(3)
_cell_angle_beta                 88.913(2)
_cell_angle_gamma                82.753(2)
_cell_volume                     592.13(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5028
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      74.5980
_cell_measurement_theta_min      2.3880
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.116
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.568
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             284
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 4 3 0.0545
3 2 4 0.0545
0 -4 -3 0.0489
-3 -2 -4 0.0624
-1 -1 11 0.0168
1 1 -11 0.0056

_exptl_crystal_size_max          0.159
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.022
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
-0.2557 3.7092 2.5819 0.0278 0.1083 0.9937
3.0886 1.9513 4.2487 0.2258 0.9371 0.2661
0.2152 -3.7162 -2.6235 -0.0306 -0.1197 -0.9923
-3.2565 -1.5254 -4.0765 -0.2317 -0.9625 -0.1410
-0.9411 -0.6086 11.2679 0.9723 -0.2337 -0.0089
0.9411 0.6086 -11.2679 -0.9723 0.2337 0.0089

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11016
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.591
_diffrn_reflns_theta_min         4.773
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -119.00 -73.00   0.50    0.05    --  -46.62-125.00 143.00   92
  2  ω   -101.00 -23.00   0.50    0.05    --  -46.62 145.00  28.00  156
  3  ω   -119.00 -60.00   0.50    0.05    --  -46.62-145.00 -22.00  118
  4  ω    -86.00 -13.00   0.50    0.05    --  -46.62 125.00-137.00  146
  5  ω     45.00 107.00   0.50    0.05    --   46.62-145.00 -22.00  124
  6  ω     34.00  95.00   0.50    0.05    --   46.62-125.00 143.00  122
  7  ω   -160.00 -73.00   0.50    0.14    --  -88.50-125.00 143.00  174
  8  ω   -152.00 -60.00   0.50    0.14    --  -88.50-145.00 -22.00  184
  9  ω    -86.00 -15.00   0.50    0.14    --  -88.50 125.00-137.00  142
 10  ω   -101.00 -23.00   0.50    0.14    --  -88.50 145.00  28.00  156
 11  ω     34.00 111.00   0.50    0.14    --  106.69-125.00 143.00  154
 12  ω     95.00 178.00   0.50    0.14    --  106.69 125.00-137.00  166
 13  ω     45.00 126.00   0.50    0.14    --  106.69-145.00 -22.00  162
 14  ω     81.00 170.00   0.50    0.14    --  106.69 145.00  28.00  178
 15  ω   -119.00 -83.00   0.50    0.05    --  -46.62 -57.00-120.00   72
 16  ω   -119.00 -83.00   0.50    0.05    --  -46.62 -57.00-150.00   72
 17  ω    -30.00  29.00   0.50    0.05    --  -46.62  19.00   0.00  118
 18  ω   -119.00 -83.00   0.50    0.05    --  -46.62 -57.00 -90.00   72
 19  ω    -30.00  29.00   0.50    0.05    --  -46.62  19.00 150.00  118
 20  ω   -160.00-101.00   0.50    0.14    --  -88.50 -77.00-180.00  118
 21  ω   -160.00-101.00   0.50    0.14    --  -88.50 -77.00 150.00  118
 22  ω   -160.00 -91.00   0.50    0.14    --  -88.50 -61.00 150.00  138
 23  ω    -51.00 -16.00   0.50    0.14    --  -88.50  45.00  60.00   70
 24  ω   -163.00 -73.00   0.50    0.14    --  -88.50 -30.00-180.00  180
 25  ω    -51.00 -16.00   0.50    0.14    --  -88.50  45.00  90.00   70
 26  ω    -51.00 -16.00   0.50    0.14    --  -88.50  45.00   0.00   70
 27  ω     34.00 105.00   0.50    0.14    --  106.69 -94.00 -30.00  142
 28  ω     34.00  71.00   0.50    0.14    --  106.69 -61.00  30.00   74
 29  ω     34.00 101.00   0.50    0.14    --  106.69 -77.00 120.00  134
 30  ω     34.00  71.00   0.50    0.14    --  106.69 -61.00 -90.00   74
 31  ω     89.00 178.00   0.50    0.14    --  106.69  15.00-120.00  178
 32  ω     95.00 178.00   0.50    0.14    --  106.69 125.00 150.00  166
 33  ω     34.00  71.00   0.50    0.14    --  106.69 -61.00-150.00   74
 34  ω     34.00 111.00   0.50    0.14    --  106.69-125.00-120.00  154
 35  ω     89.00 178.00   0.50    0.14    --  106.69  15.00   0.00  178
 36  ω     34.00 101.00   0.50    0.14    --  106.69 -77.00 -30.00  134
 37  ω     34.00  71.00   0.50    0.14    --  106.69 -61.00 120.00   74
 38  ω     34.00  71.00   0.50    0.14    --  106.69 -61.00-180.00   74
 39  ω     32.00 121.00   0.50    0.05    --   46.62  37.00 120.00  178
 40  ω     32.00 121.00   0.50    0.05    --   46.62  37.00 -60.00  178
 41  ω     32.00 121.00   0.50    0.05    --   46.62  37.00-150.00  178
 42  ω     32.00 121.00   0.50    0.05    --   46.62  37.00  30.00  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0087525000
_diffrn_orient_matrix_UB_12      -0.0507449000
_diffrn_orient_matrix_UB_13      0.0828138000
_diffrn_orient_matrix_UB_21      0.2693399000
_diffrn_orient_matrix_UB_22      0.0448547000
_diffrn_orient_matrix_UB_23      0.0041722000
_diffrn_orient_matrix_UB_31      -0.0850459000
_diffrn_orient_matrix_UB_32      0.2578511000
_diffrn_orient_matrix_UB_33      0.0060321000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2181
_reflns_number_total             2363
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.634
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0375
_refine_ls_restrained_S_all      1.080
_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)+(0.0550P)²+0.3000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1002
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_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 0.50953(7) -0.20512(7) 0.39480(2) 0.02036(15) Uani 1 1 d . . . . .
S2 S 0.35135(8) 0.78749(8) 0.11590(2) 0.02390(15) Uani 1 1 d . . . . .
O2 O 0.6706(2) -0.2000(2) 0.45415(7) 0.0248(3) Uani 1 1 d . . . . .
O3 O 0.4626(2) 0.3345(2) 0.20646(7) 0.0266(3) Uani 1 1 d . . . . .
O1 O 0.5897(2) -0.3345(2) 0.33642(7) 0.0283(3) Uani 1 1 d . . . . .
N2 N 0.1980(3) -0.2838(3) 0.48916(9) 0.0214(3) Uani 1 1 d . . . . .
N3 N 0.1288(3) -0.2578(3) 0.54500(9) 0.0265(4) Uani 1 1 d . . . . .
N1 N 0.2593(3) -0.3291(3) 0.42648(9) 0.0246(3) Uani 1 1 d . . . . .
C1 C 0.3895(3) 0.0813(3) 0.36157(10) 0.0211(4) Uani 1 1 d . . . . .
H1A H 0.325066 0.163600 0.401528 0.025 Uiso 1 1 calc R U . . .
H1B H 0.520387 0.161004 0.339057 0.025 Uiso 1 1 calc R U . . .
C6 C -0.0575(3) 0.7881(3) 0.18407(10) 0.0217(4) Uani 1 1 d . . . . .
H6 H -0.183454 0.744478 0.214562 0.026 Uiso 1 1 calc R U . . .
C5 C 0.1642(3) 0.6532(3) 0.17817(10) 0.0212(4) Uani 1 1 d . . . . .
C2 C 0.1863(3) 0.0843(3) 0.30675(10) 0.0229(4) Uani 1 1 d . . . . .
H2A H 0.052525 0.010639 0.329976 0.027 Uiso 1 1 calc R U . . .
H2B H 0.248991 -0.004523 0.268040 0.027 Uiso 1 1 calc R U . . .
C7 C -0.0736(3) 0.9992(3) 0.13904(10) 0.0247(4) Uani 1 1 d . . . . .
H7 H -0.211150 1.109782 0.136968 0.030 Uiso 1 1 calc R U . . .
C3 C 0.0889(3) 0.3297(3) 0.27494(10) 0.0224(4) Uani 1 1 d . . . . .
H3A H -0.070184 0.327771 0.253523 0.027 Uiso 1 1 calc R U . . .
H3B H 0.066283 0.428319 0.313571 0.027 Uiso 1 1 calc R U . . .
C4 C 0.2570(3) 0.4317(3) 0.21841(10) 0.0219(4) Uani 1 1 d . . . . .
C8 C 0.1327(3) 1.0247(3) 0.09886(10) 0.0241(4) Uani 1 1 d . . . . .
C9 C 0.1815(4) 1.2244(4) 0.04522(11) 0.0311(4) Uani 1 1 d . . . . .
H9A H 0.340238 1.267449 0.054023 0.047 Uiso 1 1 calc R U . . .
H9B H 0.058400 1.353420 0.050015 0.047 Uiso 1 1 calc R U . . .
H9C H 0.177214 1.180216 -0.002731 0.047 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4355(14) . ?
S1 O1 1.4275(14) . ?
S1 N1 1.7008(16) . ?
S1 C1 1.7720(18) . ?
S2 C5 1.7262(18) . ?
S2 C8 1.7237(19) . ?
O3 C4 1.228(2) . ?
N2 N3 1.122(2) . ?
N2 N1 1.258(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.525(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.376(2) . ?
C6 C7 1.409(3) . ?
C5 C4 1.462(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.527(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.362(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.511(3) . ?
C8 C9 1.500(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 N1 108.61(8) . . ?
O2 S1 C1 109.55(8) . . ?
O1 S1 O2 120.11(8) . . ?
O1 S1 N1 102.74(8) . . ?
O1 S1 C1 110.28(9) . . ?
N1 S1 C1 104.18(8) . . ?
C8 S2 C5 91.91(9) . . ?
N3 N2 N1 173.68(17) . . ?
N2 N1 S1 112.92(12) . . ?
S1 C1 H1A 109.3 . . ?
S1 C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
C2 C1 S1 111.56(12) . . ?
C2 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
C5 C6 H6 123.5 . . ?
C5 C6 C7 112.92(17) . . ?
C7 C6 H6 123.5 . . ?
C6 C5 S2 110.75(14) . . ?
C6 C5 C4 129.55(17) . . ?
C4 C5 S2 119.62(13) . . ?
C1 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
C1 C2 C3 112.26(15) . . ?
H2A C2 H2B 107.9 . . ?
C3 C2 H2A 109.2 . . ?
C3 C2 H2B 109.2 . . ?
C6 C7 H7 123.4 . . ?
C8 C7 C6 113.12(17) . . ?
C8 C7 H7 123.4 . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 C2 113.17(15) . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
O3 C4 C5 121.04(17) . . ?
O3 C4 C3 121.99(17) . . ?
C5 C4 C3 116.96(15) . . ?
C7 C8 S2 111.30(15) . . ?
C7 C8 C9 128.11(18) . . ?
C9 C8 S2 120.59(15) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 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 C1 C2 C3 -177.34(12) . . . . ?
S2 C5 C4 O3 -3.1(2) . . . . ?
S2 C5 C4 C3 176.78(13) . . . . ?
O2 S1 N1 N2 34.05(15) . . . . ?
O2 S1 C1 C2 -170.77(12) . . . . ?
O1 S1 N1 N2 162.28(13) . . . . ?
O1 S1 C1 C2 54.90(15) . . . . ?
N1 S1 C1 C2 -54.73(14) . . . . ?
C1 S1 N1 N2 -82.65(15) . . . . ?
C1 C2 C3 C4 77.2(2) . . . . ?
C6 C5 C4 O3 -179.45(18) . . . . ?
C6 C5 C4 C3 0.5(3) . . . . ?
C6 C7 C8 S2 0.1(2) . . . . ?
C6 C7 C8 C9 179.75(18) . . . . ?
C5 S2 C8 C7 -0.37(15) . . . . ?
C5 S2 C8 C9 179.92(16) . . . . ?
C5 C6 C7 C8 0.4(2) . . . . ?
C2 C3 C4 O3 -8.0(3) . . . . ?
C2 C3 C4 C5 172.10(15) . . . . ?
C7 C6 C5 S2 -0.7(2) . . . . ?
C7 C6 C5 C4 175.91(18) . . . . ?
C8 S2 C5 C6 0.59(15) . . . . ?
C8 S2 C5 C4 -176.37(15) . . . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_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 1.450
_oxdiff_exptl_absorpt_empirical_full_min 0.713
####################################################################### 
# 
# 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_hpd188b_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 2042745'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman'
;University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2020-11-05 deposited with the CCDC.	2021-04-06 downloaded from the CCDC.
;
_audit_creation_date             2020-08-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6143)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H23 N O2 S'
_chemical_formula_sum            'C17 H23 N O2 S'
_chemical_formula_weight         305.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N S O'
_chemical_oxdiff_usercomment     194-02
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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/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                   14.0325(4)
_cell_length_b                   6.26860(10)
_cell_length_c                   18.2532(5)
_cell_angle_alpha                90
_cell_angle_beta                 110.571(3)
_cell_angle_gamma                90
_cell_volume                     1503.25(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5571
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.2670
_cell_measurement_theta_min      5.1710
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.941
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.807
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             656
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 4 -1 0.0668
-2 -4 2 0.0792
1 0 11 0.0627
-1 0 -11 0.0499
9 0 -4 0.0077
0 -4 -3 0.0822
-9 0 4 0.0136
0 4 3 0.0504

_exptl_crystal_size_max          0.151
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.023
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
1.6763 3.9926 -1.4870 0.0756 0.3072 0.9487
-1.6540 -3.9870 1.7386 -0.0808 -0.3290 -0.9409
0.9001 0.1507 10.6171 -0.2220 -0.9255 0.3068
-0.7694 0.1534 -10.6913 0.2269 0.9455 -0.2336
9.0963 0.1567 -4.4648 0.9452 -0.2277 0.2339
-0.0820 -3.9225 -2.9265 0.1911 -0.0441 -0.9806
-9.0823 -0.2872 4.3590 -0.9371 0.2258 -0.2661
-0.4335 3.9159 3.1813 -0.2448 0.0571 0.9679

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5689
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.687
_diffrn_reflns_theta_min         3.448
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -122.00 -45.00   0.50    0.21    --  -46.75 -25.00-150.00  154
  2  ω    -23.00  30.00   0.50    0.21    --  -46.75  25.00  13.00  106
  3  ω    -22.00   3.00   0.50    0.21    --   46.75 -25.00-150.00   50
  4  ω     58.00 100.00   0.50    0.21    --   46.75  25.00  13.00   84
  5  ω   -111.00 -81.00   0.50    0.83    --  -88.50 -25.00-150.00   60
  6  ω     91.00 178.00   0.50    0.83    --  106.69  25.00  13.00  174
  7  ω    -29.00  27.00   0.50    0.21    --  -46.75  19.00 150.00  112
  8  ω     85.00 117.00   0.50    0.21    --   46.75  57.00 -60.00   64
  9  ω    -51.00 -19.00   0.50    0.83    --  -88.50  45.00 150.00   64
 10  ω    -44.00 -19.00   0.50    0.83    --  -88.50  45.00 -60.00   50
 11  ω    -50.00 -25.00   0.50    0.83    --  -88.50  45.00-180.00   50
 12  ω    -50.00 -16.00   0.50    0.83    --  -88.50  45.00  90.00   68
 13  ω    -51.00 -18.00   0.50    0.83    --  -88.50  45.00   0.00   66
 14  ω    -59.00 -33.00   0.50    0.83    --  -88.50  61.00-150.00   52
 15  ω     86.00 111.00   0.50    0.83    --  106.69-125.00-150.00   50
 16  ω     65.00 105.00   0.50    0.83    --  106.69 -94.00   0.00   80
 17  ω     36.00  64.00   0.50    0.83    --  106.69-125.00-150.00   56
 18  ω     35.00  66.00   0.50    0.83    --  106.69 -61.00-150.00   62
 19  ω     34.00  59.00   0.50    0.83    --  106.69 -61.00  60.00   50
 20  ω     60.00  98.00   0.50    0.83    --  106.69 -77.00  90.00   76
 21  ω     63.00  93.00   0.50    0.83    --  106.69 -77.00  60.00   60
 22  ω     34.00  59.00   0.50    0.83    --  106.69 -61.00  90.00   50
 23  ω     34.00  70.00   0.50    0.83    --  106.69 -61.00-120.00   72
 24  ω     76.00 105.00   0.50    0.83    --  106.69 -94.00-150.00   58
 25  ω     46.00  72.00   0.50    0.83    --  106.69 -77.00 -60.00   52
 26  ω     74.00 100.00   0.50    0.83    --  106.69 -77.00 -60.00   52
 27  ω     36.00  61.00   0.50    0.83    --  106.69 -94.00-150.00   50
 28  ω     34.00  62.00   0.50    0.83    --  106.69 -61.00 -90.00   56
 29  ω     48.00  94.00   0.50    0.83    --  106.69 -77.00 -90.00   92
 30  ω     34.00  59.00   0.50    0.83    --  106.69 -61.00 -60.00   50
 31  ω     66.00  92.00   0.50    0.83    --  106.69 -77.00 120.00   52
 32  ω     37.00  70.00   0.50    0.83    --  106.69 -61.00   0.00   66
 33  ω    110.00 135.00   0.50    0.83    --  106.69  25.00  14.00   50
 34  ω     87.00 113.00   0.50    0.21    --   46.75  57.00 -90.00   52
 35  ω    -57.00 -20.00   0.50    0.83    --  -88.50  61.00  60.00   74
 36  ω   -144.00-118.00   0.50    0.83    --  -88.50 -77.00  90.00   52
 37  ω   -151.00-102.00   0.50    0.83    --  -88.50 -77.00  30.00   98
 38  ω    117.00 143.00   0.50    0.83    --  106.69 125.00  60.00   52
 39  ω     57.00  83.00   0.50    0.83    --  106.69 -77.00-180.00   52
 40  ω    153.00 178.00   0.50    0.83    --  106.69 125.00  60.00   50
 41  ω     80.00 105.00   0.50    0.83    --  106.69 -94.00  90.00   50
 42  ω     34.00  60.00   0.50    0.83    --  106.69 -61.00  30.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0905970000
_diffrn_orient_matrix_UB_12      -0.0296000000
_diffrn_orient_matrix_UB_13      -0.0281679000
_diffrn_orient_matrix_UB_21      -0.0668350000
_diffrn_orient_matrix_UB_22      0.0742446000
_diffrn_orient_matrix_UB_23      -0.0825608000
_diffrn_orient_matrix_UB_31      0.0329050000
_diffrn_orient_matrix_UB_32      0.2322816000
_diffrn_orient_matrix_UB_33      0.0228102000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5110
_reflns_number_total             5689
_reflns_special_details          
;
 _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 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         5689
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0445
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0400P)²+1.2000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1096
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.6671(10)
 0.3329(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
3.a Ternary CH refined with riding coordinates:
 C12(H12), C10(H10), C15(H15)
3.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C1(H1A,H1B), C9(H9A,H9B), C16(H16A,H16B), C13(H13A,H13B),
 C17(H17A,H17B), C11(H11A,H11B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C7(H7), C6(H6), C5(H5), C4(H4)
;
_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 0.38540(4) 0.62255(8) 0.35436(3) 0.01526(14) Uani 1 1 d . . . . .
O1 O 0.43495(11) 0.6780(2) 0.43525(8) 0.0191(3) Uani 1 1 d . . . . .
O2 O 0.32323(11) 0.7834(2) 0.30248(8) 0.0215(3) Uani 1 1 d . . . . .
N1 N 0.31276(13) 0.4214(3) 0.35057(10) 0.0188(4) Uani 1 1 d . . . . .
H1 H 0.2577 0.4087 0.3106 0.023 Uiso 1 1 calc R U . . .
C14 C 0.42902(15) 0.5061(3) 0.22557(11) 0.0178(4) Uani 1 1 d . . . . .
H14A H 0.3940 0.6347 0.2007 0.021 Uiso 1 1 calc R U . . .
H14B H 0.3793 0.3923 0.2162 0.021 Uiso 1 1 calc R U . . .
C8 C 0.48054(15) 0.5432(3) 0.31397(11) 0.0148(4) Uani 1 1 d . . . . .
C1 C 0.33569(16) 0.2596(4) 0.41173(12) 0.0196(4) Uani 1 1 d . . . . .
H1A H 0.3995 0.2951 0.4528 0.024 Uiso 1 1 calc R U . . .
H1B H 0.3443 0.1228 0.3899 0.024 Uiso 1 1 calc R U . . .
C9 C 0.55763(16) 0.7264(3) 0.32833(12) 0.0186(4) Uani 1 1 d . . . . .
H9A H 0.5898 0.7514 0.3841 0.022 Uiso 1 1 calc R U . . .
H9B H 0.5231 0.8562 0.3043 0.022 Uiso 1 1 calc R U . . .
C16 C 0.56508(17) 0.2423(3) 0.23002(12) 0.0203(4) Uani 1 1 d . . . . .
H16A H 0.6160 0.2026 0.2078 0.024 Uiso 1 1 calc R U . . .
H16B H 0.5164 0.1264 0.2208 0.024 Uiso 1 1 calc R U . . .
C13 C 0.53489(16) 0.3386(3) 0.35395(12) 0.0170(4) Uani 1 1 d . . . . .
H13A H 0.4862 0.2232 0.3456 0.020 Uiso 1 1 calc R U . . .
H13B H 0.5667 0.3618 0.4098 0.020 Uiso 1 1 calc R U . . .
C12 C 0.61614(16) 0.2805(3) 0.31840(12) 0.0184(4) Uani 1 1 d . . . . .
H12 H 0.6515 0.1503 0.3433 0.022 Uiso 1 1 calc R U . . .
C10 C 0.63871(17) 0.6665(4) 0.29294(13) 0.0208(4) Uani 1 1 d . . . . .
H10 H 0.6882 0.7828 0.3019 0.025 Uiso 1 1 calc R U . . .
C15 C 0.51075(16) 0.4456(4) 0.19088(12) 0.0197(4) Uani 1 1 d . . . . .
H15 H 0.4783 0.4210 0.1345 0.024 Uiso 1 1 calc R U . . .
C17 C 0.58798(17) 0.6275(4) 0.20477(13) 0.0215(5) Uani 1 1 d . . . . .
H17A H 0.5538 0.7563 0.1793 0.026 Uiso 1 1 calc R U . . .
H17B H 0.6392 0.5906 0.1825 0.026 Uiso 1 1 calc R U . . .
C2 C 0.25316(16) 0.2403(4) 0.44688(12) 0.0196(4) Uani 1 1 d . . . . .
C3 C 0.24632(17) 0.0533(4) 0.48606(13) 0.0239(5) Uani 1 1 d . . . . .
H3 H 0.2913 -0.0581 0.4892 0.029 Uiso 1 1 calc R U . . .
C11 C 0.69314(16) 0.4630(4) 0.33252(13) 0.0218(4) Uani 1 1 d . . . . .
H11A H 0.7257 0.4872 0.3883 0.026 Uiso 1 1 calc R U . . .
H11B H 0.7454 0.4252 0.3114 0.026 Uiso 1 1 calc R U . . .
C7 C 0.18444(17) 0.4043(4) 0.44184(13) 0.0228(5) Uani 1 1 d . . . . .
H7 H 0.1878 0.5297 0.4156 0.027 Uiso 1 1 calc R U . . .
C6 C 0.11050(19) 0.3809(4) 0.47603(15) 0.0292(5) Uani 1 1 d . . . . .
H6 H 0.0645 0.4908 0.4722 0.035 Uiso 1 1 calc R U . . .
C5 C 0.10488(18) 0.1962(5) 0.51556(14) 0.0302(6) Uani 1 1 d . . . . .
H5 H 0.0558 0.1822 0.5387 0.036 Uiso 1 1 calc R U . . .
C4 C 0.17302(18) 0.0319(4) 0.52043(14) 0.0290(5) Uani 1 1 d . . . . .
H4 H 0.1695 -0.0931 0.5468 0.035 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 1.4364(15) . ?
S1 O2 1.4470(15) . ?
S1 N1 1.6073(18) . ?
S1 C8 1.807(2) . ?
N1 H1 0.8600 . ?
N1 C1 1.459(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C8 1.536(3) . ?
C14 C15 1.540(3) . ?
C8 C9 1.536(3) . ?
C8 C13 1.539(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.513(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.539(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C12 1.536(3) . ?
C16 C15 1.527(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C12 1.541(3) . ?
C12 H12 0.9800 . ?
C12 C11 1.532(3) . ?
C10 H10 0.9800 . ?
C10 C17 1.534(3) . ?
C10 C11 1.531(3) . ?
C15 H15 0.9800 . ?
C15 C17 1.532(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C2 C3 1.394(3) . ?
C2 C7 1.390(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C7 H7 0.9300 . ?
C7 C6 1.394(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.381(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.387(4) . ?
C4 H4 0.9300 . ?

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 117.84(9) . . ?
O1 S1 N1 107.73(9) . . ?
O1 S1 C8 109.01(9) . . ?
O2 S1 N1 106.92(9) . . ?
O2 S1 C8 106.66(9) . . ?
N1 S1 C8 108.36(9) . . ?
S1 N1 H1 118.4 . . ?
C1 N1 S1 123.15(14) . . ?
C1 N1 H1 118.4 . . ?
H14A C14 H14B 108.3 . . ?
C8 C14 H14A 109.9 . . ?
C8 C14 H14B 109.9 . . ?
C8 C14 C15 109.00(16) . . ?
C15 C14 H14A 109.9 . . ?
C15 C14 H14B 109.9 . . ?
C14 C8 S1 109.13(14) . . ?
C14 C8 C13 110.10(16) . . ?
C9 C8 S1 107.57(14) . . ?
C9 C8 C14 109.63(16) . . ?
C9 C8 C13 109.88(16) . . ?
C13 C8 S1 110.49(13) . . ?
N1 C1 H1A 109.1 . . ?
N1 C1 H1B 109.1 . . ?
N1 C1 C2 112.59(18) . . ?
H1A C1 H1B 107.8 . . ?
C2 C1 H1A 109.1 . . ?
C2 C1 H1B 109.1 . . ?
C8 C9 H9A 109.9 . . ?
C8 C9 H9B 109.9 . . ?
C8 C9 C10 109.06(17) . . ?
H9A C9 H9B 108.3 . . ?
C10 C9 H9A 109.9 . . ?
C10 C9 H9B 109.9 . . ?
H16A C16 H16B 108.2 . . ?
C12 C16 H16A 109.8 . . ?
C12 C16 H16B 109.8 . . ?
C15 C16 H16A 109.8 . . ?
C15 C16 H16B 109.8 . . ?
C15 C16 C12 109.46(17) . . ?
C8 C13 H13A 110.0 . . ?
C8 C13 H13B 110.0 . . ?
C8 C13 C12 108.32(16) . . ?
H13A C13 H13B 108.4 . . ?
C12 C13 H13A 110.0 . . ?
C12 C13 H13B 110.0 . . ?
C16 C12 C13 109.76(17) . . ?
C16 C12 H12 109.3 . . ?
C13 C12 H12 109.3 . . ?
C11 C12 C16 109.51(17) . . ?
C11 C12 C13 109.56(17) . . ?
C11 C12 H12 109.3 . . ?
C9 C10 H10 109.5 . . ?
C17 C10 C9 109.90(18) . . ?
C17 C10 H10 109.5 . . ?
C11 C10 C9 108.95(17) . . ?
C11 C10 H10 109.5 . . ?
C11 C10 C17 109.44(18) . . ?
C14 C15 H15 109.4 . . ?
C16 C15 C14 109.56(17) . . ?
C16 C15 H15 109.4 . . ?
C16 C15 C17 109.63(18) . . ?
C17 C15 C14 109.54(17) . . ?
C17 C15 H15 109.4 . . ?
C10 C17 H17A 109.8 . . ?
C10 C17 H17B 109.8 . . ?
C15 C17 C10 109.45(17) . . ?
C15 C17 H17A 109.8 . . ?
C15 C17 H17B 109.8 . . ?
H17A C17 H17B 108.2 . . ?
C3 C2 C1 119.1(2) . . ?
C7 C2 C1 122.0(2) . . ?
C7 C2 C3 119.0(2) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C12 C11 H11A 109.7 . . ?
C12 C11 H11B 109.7 . . ?
C10 C11 C12 109.73(17) . . ?
C10 C11 H11A 109.7 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C2 C7 H7 120.0 . . ?
C2 C7 C6 120.1(2) . . ?
C6 C7 H7 120.0 . . ?
C7 C6 H6 119.7 . . ?
C5 C6 C7 120.7(2) . . ?
C5 C6 H6 119.7 . . ?
C6 C5 H5 120.3 . . ?
C6 C5 C4 119.4(2) . . ?
C4 C5 H5 120.3 . . ?
C3 C4 C5 120.2(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C1 C2 121.39(18) . . . . ?
S1 C8 C9 C10 -178.71(14) . . . . ?
S1 C8 C13 C12 -179.07(14) . . . . ?
O1 S1 N1 C1 -31.22(19) . . . . ?
O1 S1 C8 C14 -174.23(14) . . . . ?
O1 S1 C8 C9 -55.36(16) . . . . ?
O1 S1 C8 C13 64.58(16) . . . . ?
O2 S1 N1 C1 -158.79(16) . . . . ?
O2 S1 C8 C14 -46.01(16) . . . . ?
O2 S1 C8 C9 72.86(15) . . . . ?
O2 S1 C8 C13 -167.20(14) . . . . ?
N1 S1 C8 C14 68.78(16) . . . . ?
N1 S1 C8 C9 -172.35(13) . . . . ?
N1 S1 C8 C13 -52.40(16) . . . . ?
N1 C1 C2 C3 159.27(19) . . . . ?
N1 C1 C2 C7 -21.3(3) . . . . ?
C14 C8 C9 C10 -60.2(2) . . . . ?
C14 C8 C13 C12 60.3(2) . . . . ?
C14 C15 C17 C10 60.0(2) . . . . ?
C8 S1 N1 C1 86.59(18) . . . . ?
C8 C14 C15 C16 59.9(2) . . . . ?
C8 C14 C15 C17 -60.4(2) . . . . ?
C8 C9 C10 C17 59.7(2) . . . . ?
C8 C9 C10 C11 -60.2(2) . . . . ?
C8 C13 C12 C16 -60.1(2) . . . . ?
C8 C13 C12 C11 60.1(2) . . . . ?
C1 C2 C3 C4 178.6(2) . . . . ?
C1 C2 C7 C6 -179.1(2) . . . . ?
C9 C8 C13 C12 -60.5(2) . . . . ?
C9 C10 C17 C15 -59.7(2) . . . . ?
C9 C10 C11 C12 60.5(2) . . . . ?
C16 C12 C11 C10 59.6(2) . . . . ?
C16 C15 C17 C10 -60.2(2) . . . . ?
C13 C8 C9 C10 61.0(2) . . . . ?
C13 C12 C11 C10 -60.9(2) . . . . ?
C12 C16 C15 C14 -60.2(2) . . . . ?
C12 C16 C15 C17 60.1(2) . . . . ?
C15 C14 C8 S1 178.20(14) . . . . ?
C15 C14 C8 C9 60.6(2) . . . . ?
C15 C14 C8 C13 -60.4(2) . . . . ?
C15 C16 C12 C13 60.7(2) . . . . ?
C15 C16 C12 C11 -59.6(2) . . . . ?
C17 C10 C11 C12 -59.7(2) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C2 C7 C6 C5 0.4(4) . . . . ?
C3 C2 C7 C6 0.4(3) . . . . ?
C11 C10 C17 C15 59.9(2) . . . . ?
C7 C2 C3 C4 -0.8(3) . . . . ?
C7 C6 C5 C4 -0.7(4) . . . . ?
C6 C5 C4 C3 0.2(4) . . . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_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 1.638
_oxdiff_exptl_absorpt_empirical_full_min 0.784
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.6671(10) 9276 5018 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.3329(10) 9292 5018 nmt -0.3856 0.0079 0.6131 -0.0013 -1.0001 0.0006 1.3875
-0.0084 0.3850

_twin_special_details            
;
Component 2 rotated by -179.7531° 
 around [0.40 0.00 0.91] (reciprocal) or [0.71 -0.00 0.71] (direct)
;
