# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_hpd485
_database_code_depnum_ccdc_archive 'CCDC 2170572'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman'
;The University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2022-05-04 deposited with the CCDC.	2023-10-09 downloaded from the CCDC.
;
_audit_creation_date             2022-01-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H15 N O2 S'
_chemical_formula_sum            'C11 H15 N O2 S'
_chemical_formula_weight         225.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S'
_chemical_oxdiff_usercomment     'HDC 404-2'
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      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                   5.99937(10)
_cell_length_b                   7.77287(15)
_cell_length_c                   11.90456(17)
_cell_angle_alpha                90.8904(14)
_cell_angle_beta                 95.3034(13)
_cell_angle_gamma                100.9668(15)
_cell_volume                     542.355(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7239
_cell_measurement_temperature    99.98(11)
_cell_measurement_theta_max      75.4800
_cell_measurement_theta_min      3.7260
_shelx_estimated_absorpt_T_max   0.863
_shelx_estimated_absorpt_T_min   0.617
_exptl_absorpt_coefficient_mu    2.489
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.367
_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    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             240
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 0 4 0.0587
1 -5 -1 0.0322
3 1 -3 0.1217
0 5 0 0.0878
-3 3 -1 0.0950
0 -1 -8 0.0379
1 0 7 0.0095

_exptl_crystal_size_max          0.215
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.061
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
-3.5232 -0.1924 3.5340 0.1451 0.5948 0.7907
0.6244 -5.0196 -0.6033 0.1877 0.7864 -0.5885
3.3656 0.9756 -3.3795 -0.1720 -0.7079 -0.6851
-0.0642 4.9649 0.0417 -0.2072 -0.8659 0.4552
-3.4807 2.6551 -1.4832 0.5807 -0.1417 0.8017
-0.2589 -0.5541 -7.5327 0.9094 -0.2180 -0.3541
0.8053 0.0948 7.3468 -0.9517 0.2285 0.2049

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10057
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.948
_diffrn_reflns_theta_min         3.731
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(11)
_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 0.951
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00  26.00   0.50    0.05    --  -46.87  95.00  32.00  210
  2  ω    -80.00 -15.00   0.50    0.05    --  -88.50  95.00  32.00  130
  3  ω    105.00 178.00   0.50    0.05    --  106.06  95.00  32.00  146
  4  ω     33.00 105.00   0.50    0.05    --  106.06 -95.00 -77.00  144
  5  ω   -120.00 -83.00   0.50    0.05    --  -46.87 -57.00-150.00   74
  6  ω   -120.00 -88.00   0.50    0.05    --  -46.87-125.00 -90.00   64
  7  ω   -120.00 -83.00   0.50    0.05    --  -46.87 -57.00 -90.00   74
  8  ω   -120.00 -83.00   0.50    0.05    --  -46.87 -57.00 -30.00   74
  9  ω   -120.00 -83.00   0.50    0.05    --  -46.87 -57.00 -60.00   74
 10  ω    -27.00  43.00   0.50    0.05    --   46.87 -37.00-180.00  140
 11  ω     -9.00  79.00   0.50    0.05    --   46.87 -95.00 -77.00  176
 12  ω     34.00  96.00   0.50    0.05    --   46.87-125.00   0.00  124
 13  ω    -51.00 -16.00   0.50    0.05    --  -88.50  45.00  60.00   70
 14  ω    -51.00 -16.00   0.50    0.05    --  -88.50  45.00-180.00   70
 15  ω   -160.00-101.00   0.50    0.05    --  -88.50 -77.00  30.00  118
 16  ω    -51.00 -16.00   0.50    0.05    --  -88.50  45.00   0.00   70
 17  ω   -163.00 -73.00   0.50    0.05    --  -88.50 -30.00  60.00  180
 18  ω   -160.00 -83.00   0.50    0.05    --  -88.50 -95.00 -77.00  154
 19  ω   -160.00-101.00   0.50    0.05    --  -88.50 -77.00-150.00  118
 20  ω    -51.00 -16.00   0.50    0.05    --  -88.50  45.00  30.00   70
 21  ω    -71.00 -15.00   0.50    0.05    --  -88.50  61.00 150.00  112
 22  ω     33.00 106.00   0.50    0.05    --  106.06 -94.00 -30.00  146
 23  ω     89.00 178.00   0.50    0.05    --  106.06  15.00  60.00  178
 24  ω     34.00 112.00   0.50    0.05    --  106.06-125.00 -90.00  156
 25  ω     33.00 106.00   0.50    0.05    --  106.06 -94.00 150.00  146
 26  ω     33.00 106.00   0.50    0.05    --  106.06 -94.00  30.00  146
 27  ω     33.00  71.00   0.50    0.05    --  106.06 -61.00-180.00   76
 28  ω     33.00 106.00   0.50    0.05    --  106.06 -94.00 -60.00  146
 29  ω     33.00  71.00   0.50    0.05    --  106.06 -61.00  60.00   76
 30  ω     95.00 178.00   0.50    0.05    --  106.06 125.00 -30.00  166
 31  ω     33.00 101.00   0.50    0.05    --  106.06 -77.00 120.00  136
 32  ω     92.00 178.00   0.50    0.05    --  106.06  45.00 -60.00  172
 33  ω   -120.00 -83.00   0.50    0.05    --  -46.87 -57.00 150.00   74
 34  ω     31.00 120.00   0.50    0.05    --   46.87  55.00-155.32  178
 35  ω     32.00 121.00   0.50    0.05    --   46.87  37.00   0.00  178
 36  ω     31.00 120.00   0.50    0.05    --   46.87  55.00 -68.09  178
 37  ω     31.00 120.00   0.50    0.05    --   46.87  55.00 127.62  178
 38  ω     32.00 120.00   0.50    0.05    --   46.87  53.00   9.62  176
 39  ω     31.00 120.00   0.50    0.05    --   46.87  55.00-102.99  178
 40  ω     32.00 120.00   0.50    0.05    --   46.87  53.00  48.81  176
 41  ω   -161.00-108.00   0.50    0.05    --  -88.50 -45.00 120.00  106
;
_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      -0.1515638000
_diffrn_orient_matrix_UB_12      -0.0427495000
_diffrn_orient_matrix_UB_13      -0.1123788000
_diffrn_orient_matrix_UB_21      -0.1132593000
_diffrn_orient_matrix_UB_22      -0.1762581000
_diffrn_orient_matrix_UB_23      0.0457907000
_diffrn_orient_matrix_UB_31      -0.1823967000
_diffrn_orient_matrix_UB_32      0.0889360000
_diffrn_orient_matrix_UB_33      0.0467410000
_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             2156
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0074(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0321
_refine_ls_restrained_S_all      1.087
_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)+(0.0364P)²+0.2610P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0835
_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:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B), C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C2(H2), C3(H3), C4(H4)
;
_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 0.48915(5) 0.73102(4) 0.47692(3) 0.01598(13) Uani 1 1 d . . . . .
O1 O 0.71433(17) 0.85337(13) 0.47391(8) 0.0193(2) Uani 1 1 d . . . . .
O2 O 0.34842(17) 0.60141(13) 0.83627(8) 0.0206(2) Uani 1 1 d . . . . .
N1 N 0.2756(2) 0.81264(16) 0.41520(10) 0.0177(3) Uani 1 1 d . . . . .
C1 C 0.2268(2) 0.79825(17) 0.29603(12) 0.0168(3) Uani 1 1 d . . . . .
C7 C 0.4127(2) 0.75340(18) 0.62037(11) 0.0160(3) Uani 1 1 d . . . . .
H7 H 0.388524 0.875644 0.633374 0.019 Uiso 1 1 calc R U . . .
C8 C 0.1945(2) 0.62482(19) 0.64034(12) 0.0181(3) Uani 1 1 d . . . . .
H8A H 0.062800 0.654888 0.593729 0.022 Uiso 1 1 calc R U . . .
H8B H 0.208285 0.504033 0.618796 0.022 Uiso 1 1 calc R U . . .
C11 C 0.6128(2) 0.72283(18) 0.70136(12) 0.0175(3) Uani 1 1 d . . . . .
H11A H 0.650741 0.607606 0.683429 0.021 Uiso 1 1 calc R U . . .
H11B H 0.748512 0.814807 0.692853 0.021 Uiso 1 1 calc R U . . .
C5 C -0.0306(3) 0.8330(2) 0.13409(13) 0.0240(3) Uani 1 1 d . . . . .
H5 H -0.164921 0.869142 0.102540 0.029 Uiso 1 1 calc R U . . .
C6 C 0.0264(2) 0.84749(18) 0.24996(13) 0.0195(3) Uani 1 1 d . . . . .
H6 H -0.070425 0.890644 0.297743 0.023 Uiso 1 1 calc R U . . .
C9 C 0.1582(2) 0.63616(19) 0.76534(12) 0.0196(3) Uani 1 1 d . . . . .
H9A H 0.132574 0.754851 0.784393 0.024 Uiso 1 1 calc R U . . .
H9B H 0.019890 0.550604 0.779784 0.024 Uiso 1 1 calc R U . . .
C2 C 0.3678(2) 0.73530(18) 0.22542(12) 0.0187(3) Uani 1 1 d . . . . .
H2 H 0.506781 0.705430 0.256121 0.022 Uiso 1 1 calc R U . . .
C3 C 0.3048(3) 0.7162(2) 0.10976(13) 0.0223(3) Uani 1 1 d . . . . .
H3 H 0.397861 0.668571 0.062022 0.027 Uiso 1 1 calc R U . . .
C4 C 0.1072(3) 0.7662(2) 0.06387(13) 0.0251(3) Uani 1 1 d . . . . .
H4 H 0.066046 0.754947 -0.015278 0.030 Uiso 1 1 calc R U . . .
C10 C 0.5499(2) 0.7275(2) 0.82194(12) 0.0203(3) Uani 1 1 d . . . . .
H10A H 0.677727 0.703162 0.874042 0.024 Uiso 1 1 calc R U . . .
H10B H 0.524696 0.846190 0.841426 0.024 Uiso 1 1 calc R U . . .
H1 H 0.249(3) 0.901(2) 0.4483(16) 0.024 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 O1 1.5007(10) . ?
S1 N1 1.6535(12) . ?
S1 C7 1.8228(14) . ?
O2 C9 1.4265(17) . ?
O2 C10 1.4294(17) . ?
N1 C1 1.4200(18) . ?
N1 H1 0.84(2) . ?
C1 C6 1.397(2) . ?
C1 C2 1.392(2) . ?
C7 H7 1.0000 . ?
C7 C8 1.5285(19) . ?
C7 C11 1.5261(19) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.527(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C10 1.519(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(2) . ?
C5 C4 1.389(2) . ?
C6 H6 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C2 H2 0.9500 . ?
C2 C3 1.392(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(2) . ?
C4 H4 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 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
O1 S1 N1 112.11(6) . . ?
O1 S1 C7 105.19(6) . . ?
N1 S1 C7 95.77(6) . . ?
C9 O2 C10 110.97(11) . . ?
S1 N1 H1 114.8(13) . . ?
C1 N1 S1 120.14(10) . . ?
C1 N1 H1 117.4(13) . . ?
C6 C1 N1 117.55(13) . . ?
C2 C1 N1 122.65(13) . . ?
C2 C1 C6 119.80(13) . . ?
S1 C7 H7 108.8 . . ?
C8 C7 S1 111.73(9) . . ?
C8 C7 H7 108.8 . . ?
C11 C7 S1 107.78(9) . . ?
C11 C7 H7 108.8 . . ?
C11 C7 C8 110.83(11) . . ?
C7 C8 H8A 110.0 . . ?
C7 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
C9 C8 C7 108.46(11) . . ?
C9 C8 H8A 110.0 . . ?
C9 C8 H8B 110.0 . . ?
C7 C11 H11A 109.8 . . ?
C7 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
C10 C11 C7 109.54(11) . . ?
C10 C11 H11A 109.8 . . ?
C10 C11 H11B 109.8 . . ?
C6 C5 H5 119.7 . . ?
C6 C5 C4 120.53(14) . . ?
C4 C5 H5 119.7 . . ?
C1 C6 H6 120.2 . . ?
C5 C6 C1 119.69(14) . . ?
C5 C6 H6 120.2 . . ?
O2 C9 C8 112.08(11) . . ?
O2 C9 H9A 109.2 . . ?
O2 C9 H9B 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.86(14) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.37(14) . . ?
C4 C3 H3 119.8 . . ?
C5 C4 H4 120.2 . . ?
C3 C4 C5 119.69(14) . . ?
C3 C4 H4 120.2 . . ?
O2 C10 C11 111.38(11) . . ?
O2 C10 H10A 109.4 . . ?
O2 C10 H10B 109.4 . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
H10A C10 H10B 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 C6 171.35(10) . . . . ?
S1 N1 C1 C2 -7.62(18) . . . . ?
S1 C7 C8 C9 173.23(9) . . . . ?
S1 C7 C11 C10 -176.03(9) . . . . ?
O1 S1 N1 C1 82.23(11) . . . . ?
O1 S1 C7 C8 -175.30(9) . . . . ?
O1 S1 C7 C11 -53.30(10) . . . . ?
N1 S1 C7 C8 69.90(10) . . . . ?
N1 S1 C7 C11 -168.10(9) . . . . ?
N1 C1 C6 C5 -178.94(13) . . . . ?
N1 C1 C2 C3 176.82(13) . . . . ?
C1 C2 C3 C4 2.7(2) . . . . ?
C7 S1 N1 C1 -168.78(11) . . . . ?
C7 C8 C9 O2 -57.07(15) . . . . ?
C7 C11 C10 O2 56.88(15) . . . . ?
C8 C7 C11 C10 -53.48(14) . . . . ?
C11 C7 C8 C9 53.01(14) . . . . ?
C6 C1 C2 C3 -2.1(2) . . . . ?
C6 C5 C4 C3 -1.0(2) . . . . ?
C9 O2 C10 C11 -61.12(14) . . . . ?
C2 C1 C6 C5 0.1(2) . . . . ?
C2 C3 C4 C5 -1.1(2) . . . . ?
C4 C5 C6 C1 1.5(2) . . . . ?
C10 O2 C9 C8 61.68(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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.575
_oxdiff_exptl_absorpt_empirical_full_min 0.700
####################################################################### 
# 
# 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_hpd539
_database_code_depnum_ccdc_archive 'CCDC 2176484'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman'
;The University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2022-06-01 deposited with the CCDC.	2023-10-09 downloaded from the CCDC.
;
_audit_creation_date             2022-05-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H14 N2 O S'
_chemical_formula_sum            'C11 H14 N2 O S'
_chemical_formula_weight         222.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S'
_chemical_oxdiff_usercomment     'HDC 577-5'
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                   6.3363(2)
_cell_length_b                   21.0331(7)
_cell_length_c                   8.3324(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.395(3)
_cell_angle_gamma                90
_cell_volume                     1105.55(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4618
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.9180
_cell_measurement_theta_min      4.2400
_shelx_estimated_absorpt_T_max   0.866
_shelx_estimated_absorpt_T_min   0.668
_exptl_absorpt_coefficient_mu    2.394
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.804
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.336
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             472
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -6 5 0.0320
4 0 0 0.0776
0 6 -5 0.0283
-4 0 0 0.0858
0 14 -1 0.0353
1 -13 0 0.0167

_exptl_crystal_size_max          0.183
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.062
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
0.0104 -6.3609 4.7632 -0.0234 -0.1054 0.9942
4.0605 -0.1830 0.3551 0.2265 0.9396 0.2565
0.0531 6.3723 -4.7683 0.0270 0.1203 -0.9924
-4.0934 -0.2718 -0.0163 -0.2300 -0.9550 -0.1873
0.2757 13.5698 -0.5059 -0.7690 0.3683 -0.5224
0.8092 -13.3750 -0.2745 0.8905 -0.1184 0.4392

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            10390
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.442
_diffrn_reflns_theta_min         4.204
_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 0.998
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -21.00  75.00   0.50    0.07    --   46.75 -86.00 100.00  192
  2  ω     34.00 135.00   0.50    0.29    --  106.69 -86.00 100.00  202
  3  ω     34.00  71.00   0.50    0.29    --  106.69 -61.00  90.00   74
  4  ω     35.00  71.00   0.50    0.29    --  106.69 -61.00 120.00   72
  5  ω     34.00 105.00   0.50    0.29    --  106.69 -94.00   0.00  142
  6  ω     39.00  65.00   0.50    0.29    --  106.69 -61.00 -90.00   52
  7  ω     34.00  71.00   0.50    0.29    --  106.69 -61.00-120.00   74
  8  ω     34.00  71.00   0.50    0.29    --  106.69 -61.00 -60.00   74
  9  ω     34.00  71.00   0.50    0.29    --  106.69 -61.00 -30.00   74
 10  ω     34.00 111.00   0.50    0.29    --  106.69-125.00-120.00  154
 11  ω     34.00  71.00   0.50    0.29    --  106.69 -61.00-180.00   74
 12  ω     83.00 119.00   0.50    0.07    --   46.75  57.00-150.00   72
 13  ω    101.00 178.00   0.50    0.29    --  106.69  86.00-141.00  154
 14  ω     91.00 178.00   0.50    0.29    --  106.69  61.00 -90.00  174
 15  ω    -51.00 -16.00   0.50    0.29    --  -88.50  45.00-150.00   70
 16  ω    -75.00  26.00   0.50    0.07    --  -46.75  86.00-141.00  202
 17  ω    -51.00 -16.00   0.50    0.29    --  -88.50  45.00  60.00   70
 18  ω   -116.00 -15.00   0.50    0.29    --  -88.50  86.00-141.00  202
 19  ω   -119.00 -83.00   0.50    0.07    --  -46.75 -57.00-150.00   72
 20  ω   -119.00 -87.00   0.50    0.07    --  -46.75-125.00 -90.00   64
 21  ω   -160.00-101.00   0.50    0.29    --  -88.50 -77.00  30.00  118
 22  ω   -119.00 -83.00   0.50    0.07    --  -46.75 -57.00 120.00   72
 23  ω   -160.00 -79.00   0.50    0.29    --  -88.50 -86.00 100.00  162
 24  ω   -160.00 -91.00   0.50    0.29    --  -88.50 -61.00 150.00  138
;
_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      0.0605969000
_diffrn_orient_matrix_UB_12      -0.0611361000
_diffrn_orient_matrix_UB_13      -0.0866959000
_diffrn_orient_matrix_UB_21      0.2317577000
_diffrn_orient_matrix_UB_22      0.0227187000
_diffrn_orient_matrix_UB_23      0.0077064000
_diffrn_orient_matrix_UB_31      0.0473270000
_diffrn_orient_matrix_UB_32      -0.0333444000
_diffrn_orient_matrix_UB_33      0.1640817000
_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                2070
_reflns_number_total             2229
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0417
_refine_ls_restrained_S_all      1.059
_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+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1050
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C8(H8), C9(H9), C4(H4)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.36144(7) 0.58756(2) 0.56357(5) 0.02185(15) Uani 1 1 d . . . . .
O1 O 0.2524(2) 0.53733(6) 0.45799(15) 0.0252(3) Uani 1 1 d . . . . .
N1 N 0.5415(2) 0.68882(7) 0.38332(17) 0.0221(3) Uani 1 1 d . . . . .
N2 N 0.6134(3) 0.59380(7) 0.52281(18) 0.0228(3) Uani 1 1 d . . . . .
H2 H 0.710249 0.568596 0.571273 0.027 Uiso 1 1 calc R U . . .
C1 C 0.6715(3) 0.63936(8) 0.4109(2) 0.0205(4) Uani 1 1 d . . . . .
C2 C 0.8605(3) 0.63181(9) 0.3409(2) 0.0240(4) Uani 1 1 d . . . . .
H2A H 0.949380 0.595998 0.364606 0.029 Uiso 1 1 calc R U . . .
C5 C 0.5967(3) 0.73392(9) 0.2793(2) 0.0237(4) Uani 1 1 d . . . . .
C3 C 0.9141(3) 0.67858(9) 0.2351(2) 0.0282(4) Uani 1 1 d . . . . .
H3 H 1.042192 0.675333 0.184877 0.034 Uiso 1 1 calc R U . . .
C6 C 0.4218(3) 0.55096(9) 0.7586(2) 0.0260(4) Uani 1 1 d . . . . .
H6 H 0.516740 0.513430 0.749060 0.031 Uiso 1 1 calc R U . . .
C8 C 0.3960(4) 0.59744(10) 1.0171(2) 0.0326(5) Uani 1 1 d . . . . .
H8 H 0.428531 0.620278 1.114694 0.039 Uiso 1 1 calc R U . . .
C9 C 0.2291(4) 0.56058(10) 0.9904(2) 0.0327(5) Uani 1 1 d . . . . .
H9 H 0.128623 0.553948 1.066457 0.039 Uiso 1 1 calc R U . . .
C4 C 0.7808(3) 0.73016(9) 0.2024(2) 0.0275(4) Uani 1 1 d . . . . .
H4 H 0.814920 0.762241 0.128863 0.033 Uiso 1 1 calc R U . . .
C10 C 0.2141(3) 0.53003(10) 0.8268(2) 0.0317(5) Uani 1 1 d . . . . .
H10A H 0.088481 0.545568 0.758387 0.038 Uiso 1 1 calc R U . . .
H10B H 0.206222 0.483158 0.835326 0.038 Uiso 1 1 calc R U . . .
C7 C 0.5296(3) 0.59987(10) 0.8786(2) 0.0310(4) Uani 1 1 d . . . . .
H7A H 0.677875 0.587527 0.912651 0.037 Uiso 1 1 calc R U . . .
H7B H 0.528461 0.642921 0.830472 0.037 Uiso 1 1 calc R U . . .
C11 C 0.4458(3) 0.78851(10) 0.2522(3) 0.0328(5) Uani 1 1 d . . . . .
H11A H 0.306552 0.772584 0.208942 0.049 Uiso 1 1 calc R U . . .
H11B H 0.499360 0.818317 0.175257 0.049 Uiso 1 1 calc R U . . .
H11C H 0.432616 0.810342 0.354684 0.049 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 1.5011(13) . ?
S1 N2 1.6682(16) . ?
S1 C6 1.8060(19) . ?
N1 C1 1.333(2) . ?
N1 C5 1.353(2) . ?
N2 H2 0.8800 . ?
N2 C1 1.410(2) . ?
C1 C2 1.390(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.384(3) . ?
C5 C4 1.384(3) . ?
C5 C11 1.498(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(3) . ?
C6 H6 1.0000 . ?
C6 C10 1.546(3) . ?
C6 C7 1.548(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.313(3) . ?
C8 C7 1.496(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.502(3) . ?
C4 H4 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 N2 109.43(8) . . ?
O1 S1 C6 105.91(8) . . ?
N2 S1 C6 95.21(8) . . ?
C1 N1 C5 117.70(16) . . ?
S1 N2 H2 119.9 . . ?
C1 N2 S1 120.17(12) . . ?
C1 N2 H2 119.9 . . ?
N1 C1 N2 116.67(16) . . ?
N1 C1 C2 124.01(17) . . ?
C2 C1 N2 119.28(16) . . ?
C1 C2 H2A 121.3 . . ?
C3 C2 C1 117.31(17) . . ?
C3 C2 H2A 121.3 . . ?
N1 C5 C4 122.43(17) . . ?
N1 C5 C11 115.72(17) . . ?
C4 C5 C11 121.85(17) . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.00(18) . . ?
C4 C3 H3 120.0 . . ?
S1 C6 H6 110.1 . . ?
C10 C6 S1 109.67(14) . . ?
C10 C6 H6 110.1 . . ?
C10 C6 C7 106.91(15) . . ?
C7 C6 S1 109.95(13) . . ?
C7 C6 H6 110.1 . . ?
C9 C8 H8 123.4 . . ?
C9 C8 C7 113.24(18) . . ?
C7 C8 H8 123.4 . . ?
C8 C9 H9 123.6 . . ?
C8 C9 C10 112.82(18) . . ?
C10 C9 H9 123.6 . . ?
C5 C4 C3 118.55(17) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C6 C10 H10A 111.1 . . ?
C6 C10 H10B 111.1 . . ?
C9 C10 C6 103.21(16) . . ?
C9 C10 H10A 111.1 . . ?
C9 C10 H10B 111.1 . . ?
H10A C10 H10B 109.1 . . ?
C6 C7 H7A 111.1 . . ?
C6 C7 H7B 111.1 . . ?
C8 C7 C6 103.21(16) . . ?
C8 C7 H7A 111.1 . . ?
C8 C7 H7B 111.1 . . ?
H7A C7 H7B 109.1 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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 N2 C1 N1 22.0(2) . . . . ?
S1 N2 C1 C2 -160.22(13) . . . . ?
S1 C6 C10 C9 -126.64(15) . . . . ?
S1 C6 C7 C8 126.44(15) . . . . ?
O1 S1 N2 C1 94.08(14) . . . . ?
O1 S1 C6 C10 -61.08(15) . . . . ?
O1 S1 C6 C7 -178.35(13) . . . . ?
N1 C1 C2 C3 -0.6(3) . . . . ?
N1 C5 C4 C3 -0.8(3) . . . . ?
N2 S1 C6 C10 -173.00(13) . . . . ?
N2 S1 C6 C7 69.72(15) . . . . ?
N2 C1 C2 C3 -178.26(16) . . . . ?
C1 N1 C5 C4 0.0(3) . . . . ?
C1 N1 C5 C11 180.00(16) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C5 N1 C1 N2 178.45(15) . . . . ?
C5 N1 C1 C2 0.7(3) . . . . ?
C6 S1 N2 C1 -157.01(14) . . . . ?
C8 C9 C10 C6 4.9(2) . . . . ?
C9 C8 C7 C6 -4.8(2) . . . . ?
C10 C6 C7 C8 7.5(2) . . . . ?
C7 C6 C10 C9 -7.5(2) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C11 C5 C4 C3 179.20(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
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.387
_oxdiff_exptl_absorpt_empirical_full_min 0.705
####################################################################### 
# 
# 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_hpd534g
_database_code_depnum_ccdc_archive 'CCDC 2170581'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman'
;The University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2022-05-04 deposited with the CCDC.	2023-10-09 downloaded from the CCDC.
;
_audit_creation_date             2022-04-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H13 Br Cl N3 O2 S'
_chemical_formula_sum            'C9 H13 Br Cl N3 O2 S'
_chemical_formula_weight         342.64
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S Br Cl'
_chemical_oxdiff_usercomment     'HDc 574-1'
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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   5.5464(6)
_cell_length_b                   11.0627(10)
_cell_length_c                   11.4651(8)
_cell_angle_alpha                70.025(7)
_cell_angle_beta                 84.920(8)
_cell_angle_gamma                76.652(9)
_cell_volume                     643.26(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2707
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.9870
_cell_measurement_theta_min      4.1270
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.759
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.632
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.769
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             344
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 3 -5 0.0067
3 1 -1 0.1012
1 5 -3 0.0477
-1 6 5 0.0524
-1 -5 4 0.0272
1 -5 -5 0.0191
0 -3 5 0.0462

_exptl_crystal_size_max          0.207
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.072
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
-1.0837 2.7900 -4.8423 0.1329 0.5462 0.8271
3.4791 0.8438 -1.2606 -0.2100 -0.8766 0.4330
0.6016 5.3516 -2.7691 -0.3369 0.2565 0.9059
-0.7404 6.0531 4.5385 -0.7928 0.6089 -0.0268
-0.7717 -4.5628 3.7581 0.2122 -0.1606 -0.9639
0.8882 -5.4585 -5.2834 0.7789 -0.5986 0.1874
0.3429 -2.9972 5.1581 -0.0888 -0.3620 -0.9279

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0642
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7134
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.977
_diffrn_reflns_theta_min         4.354
_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 0.982
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     73.00  99.00   0.50    0.34    --   46.37  36.00 -92.00   52
  2  ω    102.00 138.00   0.50    1.35    --  106.69  36.00 -92.00   72
  3  ω    101.00 130.00   0.50    1.35    --  106.69  77.00 -60.00   58
  4  ω    147.00 178.00   0.50    1.35    --  106.69  77.00 -60.00   62
  5  ω    143.00 172.00   0.50    1.35    --  106.69  36.00 -92.00   58
  6  ω     91.00 135.00   0.50    1.35    --  106.69  15.00   0.00   88
  7  ω    143.00 178.00   0.50    1.35    --  106.69  15.00   0.00   70
  8  ω     85.00 116.00   0.50    0.34    --   46.37  57.00  90.00   62
  9  ω    -27.00  25.00   0.50    0.34    --   46.37 -19.00  30.00  104
 10  ω    -21.00  41.00   0.50    0.34    --   46.37 -36.00 110.00  124
 11  ω     36.00  70.00   0.50    1.35    --  106.69 -77.00 120.00   68
 12  ω     38.00  70.00   0.50    1.35    --  106.69 -61.00 120.00   64
 13  ω     39.00  71.00   0.50    1.35    --  106.69 -61.00 -90.00   64
 14  ω     35.00 100.00   0.50    1.35    --  106.69 -77.00 -90.00  130
 15  ω     76.00 103.00   0.50    1.35    --  106.69 -94.00-120.00   54
 16  ω     62.00 107.00   0.50    1.35    --  106.69-125.00-120.00   90
 17  ω     36.00  84.00   0.50    0.34    --   46.37-125.00   0.00   96
 18  ω     41.00  68.00   0.50    1.35    --  106.69-125.00 120.00   54
 19  ω     38.00  78.00   0.50    1.35    --  106.69-125.00  60.00   80
 20  ω     82.00 111.00   0.50    1.35    --  106.69-125.00 120.00   58
 21  ω     84.00 110.00   0.50    1.35    --  106.69-125.00  60.00   52
 22  ω     79.00 109.00   0.50    1.35    --  106.69-125.00  30.00   60
 23  ω     43.00  70.00   0.50    1.35    --  106.69-125.00  30.00   54
 24  ω     37.00  63.00   0.50    1.35    --  106.69 -94.00 120.00   52
 25  ω     79.00 105.00   0.50    1.35    --  106.69 -94.00 120.00   52
 26  ω     45.00  71.00   0.50    0.34    --   46.37 -99.00-180.00   52
 27  ω     71.00  97.00   0.50    1.35    --  106.69 -94.00-150.00   52
 28  ω     36.00  61.00   0.50    1.35    --  106.69 -94.00-150.00   50
 29  ω     36.00  72.00   0.50    1.35    --  106.69 -94.00-120.00   72
 30  ω     39.00  73.00   0.50    1.35    --  106.69 -94.00  60.00   68
 31  ω    -69.00 -18.00   0.50    1.35    --  -88.50  61.00  90.00  102
 32  ω    -35.00  26.00   0.50    0.34    --  -46.37  36.00 -92.00  122
 33  ω    -40.00 -14.00   0.50    1.35    --  -88.50  36.00 -92.00   52
 34  ω    -46.00 -18.00   0.50    1.35    --  -88.50  45.00-120.00   56
 35  ω    -49.00 -24.00   0.50    1.35    --  -88.50 125.00-180.00   50
 36  ω    -84.00 -58.00   0.50    1.35    --  -88.50 125.00 -30.00   52
 37  ω   -152.00 -91.00   0.50    1.35    --  -88.50 -36.00 110.00  122
 38  ω   -116.00 -70.00   0.50    0.34    --  -46.37 -36.00 110.00   92
 39  ω   -159.00-108.00   0.50    1.35    --  -88.50 -77.00 -90.00  102
 40  ω   -136.00-100.00   0.50    1.35    --  -88.50 -94.00-150.00   72
 41  ω   -117.00 -88.00   0.50    0.34    --  -46.37-125.00-120.00   58
 42  ω   -116.00 -88.00   0.50    0.34    --  -46.37-125.00  60.00   56
 43  ω     77.00 112.00   0.50    0.34    --   46.37  37.00-150.00   70
 44  ω     -4.00  25.00   0.50    0.34    --   46.37 -19.00-120.00   58
 45  ω   -148.00-104.00   0.50    1.35    --  -88.50 -77.00  60.00   88
 46  ω   -139.00-112.00   0.50    1.35    --  -88.50 -94.00 120.00   54
 47  ω    -66.00 -40.00   0.50    1.35    --  -88.50  61.00 -30.00   52
 48  ω    150.00 177.00   0.50    1.35    --  106.69  15.00 -30.00   54
 49  ω     90.00 126.00   0.50    1.35    --  106.69  15.00 -30.00   72
 50  ω     66.00 105.00   0.50    1.35    --  106.69 -94.00  30.00   78
 51  ω     34.00  64.00   0.50    1.35    --  106.69 -61.00 -30.00   60
 52  ω    153.00 178.00   0.50    1.35    --  106.69  15.00 120.00   50
 53  ω     76.00 101.00   0.50    1.35    --  106.69 -77.00-150.00   50
 54  ω     92.00 133.00   0.50    1.35    --  106.69  15.00 120.00   82
;
_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      -0.0622240000
_diffrn_orient_matrix_UB_12      -0.0896966000
_diffrn_orient_matrix_UB_13      -0.0652046000
_diffrn_orient_matrix_UB_21      -0.2731743000
_diffrn_orient_matrix_UB_22      0.0739582000
_diffrn_orient_matrix_UB_23      -0.0090416000
_diffrn_orient_matrix_UB_31      0.0548271000
_diffrn_orient_matrix_UB_32      0.0974456000
_diffrn_orient_matrix_UB_33      -0.1269237000
_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                2011
_reflns_number_total             2379
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.135
_refine_diff_density_min         -1.104
_refine_diff_density_rms         0.155
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2379
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0790
_refine_ls_restrained_S_all      1.085
_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)+(0.0100P)²+6.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1741
_refine_ls_wR_factor_ref         0.1791
_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, All N(H) groups
2. Restrained distances
 C9B-C8B
 1.6 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C8B) = Uanis(C9B) = Uanis(Cl1B)
Uanis(C9A) = Uanis(Cl1A) = Uanis(C8A)
4. Others
 Fixed Sof: Cl1A(0.65) Cl1B(0.35) H7AA(0.65) H7AB(0.65) H7BC(0.35) H7BD(0.35)
 C8A(0.65) H8AA(0.65) H8AB(0.65) C9A(0.65) H9AA(0.65) H9AB(0.65) C8B(0.35)
 H8BA(0.35) H8BB(0.35) C9B(0.35) H9BA(0.35) H9BB(0.35)
5.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C7(H7AA,H7AB), C7(H7BC,H7BD), C8A(H8AA,H8AB),
 C9A(H9AA,H9AB), C8B(H8BA,H8BB), C9B(H9BA,H9BB)
5.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C2(H2)
;
_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
Br1 Br -0.26663(17) 1.07923(9) 0.14328(8) 0.0645(4) Uani 1 1 d . . . . .
S1 S 0.7918(3) 0.69189(17) 0.49677(16) 0.0434(4) Uani 1 1 d . . . . .
Cl1A Cl 0.1681(6) 0.3216(3) 1.0392(3) 0.0607(8) Uani 0.65 1 d . . P A 1
O1 O 0.9867(9) 0.7000(5) 0.5648(5) 0.0503(13) Uani 1 1 d . . . . .
O2 O 0.8541(10) 0.6594(5) 0.3855(5) 0.0513(13) Uani 1 1 d . . . . .
N2 N 0.2765(11) 1.0092(6) 0.3934(5) 0.0436(14) Uani 1 1 d . . . . .
Cl1B Cl 0.2596(11) 0.1896(6) 0.9565(5) 0.0602(14) Uani 0.35 1 d . . P B 2
N1 N 0.6108(11) 0.8389(6) 0.4660(6) 0.0454(14) Uani 1 1 d . . . . .
H1 H 0.649486 0.890174 0.499786 0.054 Uiso 1 1 calc R U . . .
N3 N 0.3472(11) 0.8192(6) 0.3278(6) 0.0468(15) Uani 1 1 d . . . . .
C1 C 0.4007(13) 0.8903(7) 0.3909(6) 0.0432(16) Uani 1 1 d . . . . .
C4 C 0.1487(15) 0.8784(8) 0.2528(7) 0.0498(18) Uani 1 1 d . . . . .
H4 H 0.102585 0.835120 0.204467 0.060 Uiso 1 1 calc R U . . .
C3 C 0.0131(13) 1.0021(7) 0.2467(6) 0.0444(17) Uani 1 1 d . . . . .
C2 C 0.0803(14) 1.0645(8) 0.3171(7) 0.0489(18) Uani 1 1 d . . . . .
H2 H -0.010934 1.147662 0.312980 0.059 Uiso 1 1 calc R U . . .
C5 C 0.6142(14) 0.5852(7) 0.5961(7) 0.0490(18) Uani 1 1 d . . . . .
H5A H 0.457440 0.599553 0.556746 0.059 Uiso 1 1 calc R U . . .
H5B H 0.700413 0.494995 0.607912 0.059 Uiso 1 1 calc R U . . .
C6 C 0.5636(17) 0.6032(10) 0.7214(8) 0.064(2) Uani 1 1 d . . . . .
H6A H 0.718631 0.576244 0.765635 0.077 Uiso 1 1 calc R U . . .
H6B H 0.500401 0.696052 0.709111 0.077 Uiso 1 1 calc R U . . .
C7 C 0.3833(17) 0.5275(11) 0.7995(9) 0.084(4) Uani 1 1 d . . . . .
H7AA H 0.230979 0.549337 0.754113 0.101 Uiso 0.65 1 calc R U P C 1
H7AB H 0.344411 0.551234 0.874100 0.101 Uiso 0.65 1 calc R U P C 1
H7BC H 0.325171 0.568010 0.862592 0.101 Uiso 0.35 1 calc R U P D 2
H7BD H 0.242621 0.546407 0.746719 0.101 Uiso 0.35 1 calc R U P D 2
C8A C 0.490(3) 0.3825(16) 0.8343(15) 0.0607(8) Uani 0.65 1 d . . P A 1
H8AA H 0.626878 0.358724 0.890646 0.073 Uiso 0.65 1 calc R U P A 1
H8AB H 0.554380 0.361577 0.760348 0.073 Uiso 0.65 1 calc R U P A 1
C9A C 0.290(3) 0.2997(14) 0.8979(12) 0.0607(8) Uani 0.65 1 d . . P A 1
H9AA H 0.363628 0.207208 0.913732 0.073 Uiso 0.65 1 calc R U P A 1
H9AB H 0.154719 0.323763 0.840634 0.073 Uiso 0.65 1 calc R U P A 1
C8B C 0.429(5) 0.397(3) 0.859(2) 0.0602(14) Uani 0.35 1 d D . P B 2
H8BA H 0.588374 0.370234 0.899657 0.072 Uiso 0.35 1 calc R U P B 2
H8BB H 0.440401 0.352101 0.798856 0.072 Uiso 0.35 1 calc R U P B 2
C9B C 0.222(4) 0.349(3) 0.962(2) 0.0602(14) Uani 0.35 1 d D . P B 2
H9BA H 0.056760 0.401105 0.938149 0.072 Uiso 0.35 1 calc R U P B 2
H9BB H 0.259517 0.348370 1.043472 0.072 Uiso 0.35 1 calc R U P B 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
Br1 C3 1.888(6) . ?
S1 O1 1.423(6) . ?
S1 O2 1.434(5) . ?
S1 N1 1.641(6) . ?
S1 C5 1.755(8) . ?
Cl1A C9A 1.771(14) . ?
N2 C1 1.345(9) . ?
N2 C2 1.348(9) . ?
Cl1B C9B 1.75(3) . ?
N1 H1 0.8600 . ?
N1 C1 1.400(9) . ?
N3 C1 1.328(10) . ?
N3 C4 1.353(9) . ?
C4 H4 0.9300 . ?
C4 C3 1.383(11) . ?
C3 C2 1.348(11) . ?
C2 H2 0.9300 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.511(12) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.490(13) . ?
C7 H7AA 0.9700 . ?
C7 H7AB 0.9700 . ?
C7 H7BC 0.9700 . ?
C7 H7BD 0.9700 . ?
C7 C8A 1.500(19) . ?
C7 C8B 1.35(3) . ?
C8A H8AA 0.9700 . ?
C8A H8AB 0.9700 . ?
C8A C9A 1.57(2) . ?
C9A H9AA 0.9700 . ?
C9A H9AB 0.9700 . ?
C8B H8BA 0.9700 . ?
C8B H8BB 0.9700 . ?
C8B C9B 1.615(18) . ?
C9B H9BA 0.9700 . ?
C9B H9BB 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
O1 S1 O2 118.4(3) . . ?
O1 S1 N1 102.6(3) . . ?
O1 S1 C5 109.6(3) . . ?
O2 S1 N1 110.7(3) . . ?
O2 S1 C5 110.0(4) . . ?
N1 S1 C5 104.6(3) . . ?
C1 N2 C2 115.0(7) . . ?
S1 N1 H1 116.3 . . ?
C1 N1 S1 127.4(5) . . ?
C1 N1 H1 116.3 . . ?
C1 N3 C4 114.7(6) . . ?
N2 C1 N1 113.5(7) . . ?
N3 C1 N2 128.2(6) . . ?
N3 C1 N1 118.3(6) . . ?
N3 C4 H4 119.4 . . ?
N3 C4 C3 121.2(7) . . ?
C3 C4 H4 119.4 . . ?
C4 C3 Br1 119.7(6) . . ?
C2 C3 Br1 121.1(6) . . ?
C2 C3 C4 119.2(7) . . ?
N2 C2 H2 119.2 . . ?
C3 C2 N2 121.6(7) . . ?
C3 C2 H2 119.2 . . ?
S1 C5 H5A 108.9 . . ?
S1 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
C6 C5 S1 113.4(6) . . ?
C6 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
C5 C6 H6A 108.8 . . ?
C5 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C7 C6 C5 113.8(9) . . ?
C7 C6 H6A 108.8 . . ?
C7 C6 H6B 108.8 . . ?
C6 C7 H7AA 109.6 . . ?
C6 C7 H7AB 109.6 . . ?
C6 C7 H7BC 105.8 . . ?
C6 C7 H7BD 105.8 . . ?
C6 C7 C8A 110.2(9) . . ?
H7AA C7 H7AB 108.1 . . ?
H7BC C7 H7BD 106.2 . . ?
C8A C7 H7AA 109.6 . . ?
C8A C7 H7AB 109.6 . . ?
C8B C7 C6 126.0(13) . . ?
C8B C7 H7BC 105.8 . . ?
C8B C7 H7BD 105.8 . . ?
C7 C8A H8AA 109.3 . . ?
C7 C8A H8AB 109.3 . . ?
C7 C8A C9A 111.4(11) . . ?
H8AA C8A H8AB 108.0 . . ?
C9A C8A H8AA 109.3 . . ?
C9A C8A H8AB 109.3 . . ?
Cl1A C9A H9AA 108.7 . . ?
Cl1A C9A H9AB 108.7 . . ?
C8A C9A Cl1A 114.2(11) . . ?
C8A C9A H9AA 108.7 . . ?
C8A C9A H9AB 108.7 . . ?
H9AA C9A H9AB 107.6 . . ?
C7 C8B H8BA 108.7 . . ?
C7 C8B H8BB 108.7 . . ?
C7 C8B C9B 114(2) . . ?
H8BA C8B H8BB 107.6 . . ?
C9B C8B H8BA 108.7 . . ?
C9B C8B H8BB 108.7 . . ?
Cl1B C9B H9BA 112.2 . . ?
Cl1B C9B H9BB 112.2 . . ?
C8B C9B Cl1B 98(2) . . ?
C8B C9B H9BA 112.2 . . ?
C8B C9B H9BB 112.2 . . ?
H9BA C9B H9BB 109.8 . . ?

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
Br1 C3 C2 N2 178.5(5) . . . . ?
S1 N1 C1 N2 173.7(5) . . . . ?
S1 N1 C1 N3 -6.1(10) . . . . ?
S1 C5 C6 C7 171.6(6) . . . . ?
O1 S1 N1 C1 173.7(6) . . . . ?
O1 S1 C5 C6 42.1(6) . . . . ?
O2 S1 N1 C1 46.5(7) . . . . ?
O2 S1 C5 C6 173.8(5) . . . . ?
N1 S1 C5 C6 -67.3(6) . . . . ?
N3 C4 C3 Br1 -178.7(6) . . . . ?
N3 C4 C3 C2 -0.1(12) . . . . ?
C1 N2 C2 C3 1.6(10) . . . . ?
C1 N3 C4 C3 -1.4(11) . . . . ?
C4 N3 C1 N2 3.4(11) . . . . ?
C4 N3 C1 N1 -176.9(6) . . . . ?
C4 C3 C2 N2 0.0(11) . . . . ?
C2 N2 C1 N1 176.7(6) . . . . ?
C2 N2 C1 N3 -3.5(11) . . . . ?
C5 S1 N1 C1 -71.9(7) . . . . ?
C5 C6 C7 C8A 65.9(12) . . . . ?
C5 C6 C7 C8B 75(2) . . . . ?
C6 C7 C8A C9A -170.7(11) . . . . ?
C6 C7 C8B C9B 165.7(17) . . . . ?
C7 C8A C9A Cl1A -62.2(15) . . . . ?
C7 C8B C9B Cl1B 152(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
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 3.265
_oxdiff_exptl_absorpt_empirical_full_min 0.374
####################################################################### 
# 
# 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_hpd490
_database_code_depnum_ccdc_archive 'CCDC 2170584'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman'
;The University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2022-05-04 deposited with the CCDC.	2023-10-09 downloaded from the CCDC.
;
_audit_creation_date             2022-01-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H21 N O3 S'
_chemical_formula_sum            'C16 H21 N O3 S'
_chemical_formula_weight         307.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S'
_chemical_oxdiff_usercomment     'HDC 414-3'
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      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                   5.88370(10)
_cell_length_b                   9.30100(10)
_cell_length_c                   14.8817(2)
_cell_angle_alpha                72.8400(10)
_cell_angle_beta                 81.8890(10)
_cell_angle_gamma                75.0620(10)
_cell_volume                     749.973(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9522
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.8490
_cell_measurement_theta_min      3.0920
_shelx_estimated_absorpt_T_max   0.886
_shelx_estimated_absorpt_T_min   0.713
_exptl_absorpt_coefficient_mu    2.002
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.388
_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    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             328
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 5 2 0.0371
2 0 8 0.0794
0 -5 -6 0.0410
-2 -1 -9 0.0317
-4 1 -2 0.0555
-1 -4 5 0.0520
1 4 -4 0.0067

_exptl_crystal_size_max          0.181
_exptl_crystal_size_mid          0.131
_exptl_crystal_size_min          0.062
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
-1.3054 4.9434 2.3903 0.1565 0.6429 0.7498
2.0774 0.1898 8.1062 0.1286 0.5431 -0.8298
0.4252 -5.1110 -5.9535 -0.2151 -0.8899 -0.4022
-1.8944 -1.1322 -8.8100 -0.1622 -0.6817 0.7134
-3.5133 0.5694 -2.1166 0.5310 -0.1298 0.8374
-1.1006 -4.1362 4.5943 0.7643 -0.1824 -0.6185
1.3511 4.1119 -4.4632 -0.8044 0.1922 0.5622

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13752
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.355
_diffrn_reflns_theta_min         3.116
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.947
_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 -23.00   0.50    0.05    --  -46.75 -77.00 -21.00  192
  2  ω    -30.00  29.00   0.50    0.05    --  -46.75  19.00  60.00  118
  3  ω    -51.00 -16.00   0.50    0.05    --  -88.50  45.00 -30.00   70
  4  ω    -51.00 -16.00   0.50    0.05    --  -88.50  45.00 -90.00   70
  5  ω    -51.00 -16.00   0.50    0.05    --  -88.50  45.00 -60.00   70
  6  ω    -51.00 -16.00   0.50    0.05    --  -88.50  45.00  60.00   70
  7  ω    -51.00 -16.00   0.50    0.05    --  -88.50  45.00  90.00   70
  8  ω    -70.00  26.00   0.50    0.05    --  -46.75  77.00 104.00  192
  9  ω     23.00 119.00   0.50    0.05    --   46.75  77.00 104.00  192
 10  ω     83.00 178.00   0.50    0.05    --  106.69  77.00 104.00  190
 11  ω     34.00 101.00   0.50    0.05    --  106.69 -77.00 -21.00  134
 12  ω     34.00 107.00   0.50    0.05    --  106.69-106.00  54.45  146
 13  ω     34.00 105.00   0.50    0.05    --  106.69 -94.00 150.00  142
 14  ω     34.00  71.00   0.50    0.05    --  106.69 -61.00 120.00   74
 15  ω     34.00 105.00   0.50    0.05    --  106.69 -94.00 120.00  142
 16  ω     34.00 111.00   0.50    0.05    --  106.69-125.00 120.00  154
 17  ω     34.00 105.00   0.50    0.05    --  106.69 -94.00 -60.00  142
 18  ω     34.00 101.00   0.50    0.05    --  106.69 -77.00-150.00  134
 19  ω     34.00  71.00   0.50    0.05    --  106.69 -61.00-120.00   74
 20  ω     34.00 105.00   0.50    0.05    --  106.69 -94.00-150.00  142
 21  ω     34.00 101.00   0.50    0.05    --  106.69 -77.00-120.00  134
 22  ω     31.00 122.00   0.50    0.05    --   46.75  19.00   0.00  182
 23  ω     91.00 178.00   0.50    0.05    --  106.69  61.00-180.00  174
 24  ω     31.00 119.00   0.50    0.05    --   46.75  55.00-139.99  176
 25  ω     31.00 119.00   0.50    0.05    --   46.75  55.00 -55.83  176
 26  ω     33.00 120.00   0.50    0.05    --   46.75  43.00  53.47  174
 27  ω     32.00 119.00   0.50    0.05    --   46.75  52.00 -91.50  174
 28  ω     32.00 121.00   0.50    0.05    --   46.75  37.00-180.00  178
 29  ω     31.00 119.00   0.50    0.05    --   46.75  55.00  68.76  176
 30  ω    -25.00  71.00   0.50    0.05    --   46.75 -77.00 -21.00  192
 31  ω   -101.00 -15.00   0.50    0.05    --  -88.50  77.00 104.00  172
 32  ω   -119.00 -83.00   0.50    0.05    --  -46.75 -57.00 -90.00   72
 33  ω   -160.00 -65.00   0.50    0.05    --  -88.50 -77.00 -21.00  190
 34  ω   -119.00 -88.00   0.50    0.05    --  -46.75-125.00 150.00   62
 35  ω   -160.00-101.00   0.50    0.05    --  -88.50 -77.00 120.00  118
 36  ω   -160.00-101.00   0.50    0.05    --  -88.50 -77.00   0.00  118
 37  ω   -160.00-101.00   0.50    0.05    --  -88.50 -77.00-120.00  118
 38  ω   -160.00 -88.00   0.50    0.05    --  -88.50-125.00 -60.00  144
 39  ω   -160.00-101.00   0.50    0.05    --  -88.50 -77.00  30.00  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      -0.2014516000
_diffrn_orient_matrix_UB_12      -0.0547831000
_diffrn_orient_matrix_UB_13      0.0687746000
_diffrn_orient_matrix_UB_21      0.0180063000
_diffrn_orient_matrix_UB_22      0.1058408000
_diffrn_orient_matrix_UB_23      0.0599043000
_diffrn_orient_matrix_UB_31      -0.1813738000
_diffrn_orient_matrix_UB_32      0.1322963000
_diffrn_orient_matrix_UB_33      -0.0589785000
_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                2788
_reflns_number_total             2989
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.567
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.0040(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2989
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      1.070
_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)+(0.0469P)²+0.5202P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1014
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C9(H9A,H9B), C8(H8A,H8B), C12(H12A,H12B),
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C4(H4), C2(H2), C3(H3), C5(H5)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.48017(7) 0.25390(4) 0.50899(3) 0.01516(14) Uani 1 1 d . . . . .
O1 O 0.2749(2) 0.38928(13) 0.50254(8) 0.0188(3) Uani 1 1 d . . . . .
O3 O 1.0689(2) 0.29758(15) 0.09627(8) 0.0234(3) Uani 1 1 d . . . . .
O2 O 0.7534(2) 0.2386(2) 0.06206(10) 0.0405(4) Uani 1 1 d . . . . .
N1 N 0.7043(2) 0.28013(16) 0.55462(9) 0.0168(3) Uani 1 1 d . . . . .
H1 H 0.816711 0.318755 0.517441 0.020 Uiso 1 1 calc R U . . .
C7 C 0.6115(3) 0.26675(18) 0.38884(11) 0.0145(3) Uani 1 1 d . . . . .
C10 C 0.7604(3) 0.27402(19) 0.21599(11) 0.0161(3) Uani 1 1 d . . . . .
C1 C 0.7122(3) 0.23950(18) 0.65420(11) 0.0158(3) Uani 1 1 d . . . . .
C13 C 0.7188(3) 0.40735(18) 0.34498(11) 0.0177(3) Uani 1 1 d . . . . .
H13A H 0.861138 0.396054 0.377204 0.021 Uiso 1 1 calc R U . . .
H13B H 0.603745 0.502262 0.352619 0.021 Uiso 1 1 calc R U . . .
C14 C 0.7853(3) 0.42024(19) 0.23897(11) 0.0175(3) Uani 1 1 d . . . . .
H14A H 0.680628 0.512542 0.200600 0.021 Uiso 1 1 calc R U . . .
H14B H 0.949836 0.432179 0.223152 0.021 Uiso 1 1 calc R U . . .
C15 C 0.8536(3) 0.2692(2) 0.11661(12) 0.0194(4) Uani 1 1 d . . . . .
C6 C 0.8816(3) 0.28566(19) 0.68938(12) 0.0185(3) Uani 1 1 d . . . . .
H6 H 0.985589 0.341775 0.647281 0.022 Uiso 1 1 calc R U . . .
C4 C 0.7481(3) 0.1664(2) 0.84909(12) 0.0226(4) Uani 1 1 d . . . . .
H4 H 0.760200 0.141916 0.915141 0.027 Uiso 1 1 calc R U . . .
C2 C 0.5607(3) 0.15729(19) 0.71696(12) 0.0184(3) Uani 1 1 d . . . . .
H2 H 0.443613 0.126532 0.693738 0.022 Uiso 1 1 calc R U . . .
C3 C 0.5811(3) 0.1204(2) 0.81368(12) 0.0213(4) Uani 1 1 d . . . . .
H3 H 0.479255 0.062811 0.855990 0.026 Uiso 1 1 calc R U . . .
C9 C 0.9030(3) 0.13016(19) 0.28451(11) 0.0177(3) Uani 1 1 d . . . . .
H9A H 0.897235 0.035865 0.267711 0.021 Uiso 1 1 calc R U . . .
H9B H 1.069996 0.136727 0.278712 0.021 Uiso 1 1 calc R U . . .
C8 C 0.8011(3) 0.11939(19) 0.38731(12) 0.0191(3) Uani 1 1 d . . . . .
H8A H 0.731596 0.027851 0.412102 0.023 Uiso 1 1 calc R U . . .
H8B H 0.928245 0.108386 0.427600 0.023 Uiso 1 1 calc R U . . .
C5 C 0.8976(3) 0.2492(2) 0.78608(12) 0.0220(4) Uani 1 1 d . . . . .
H5 H 1.012525 0.281410 0.809614 0.026 Uiso 1 1 calc R U . . .
C12 C 0.4066(3) 0.2763(2) 0.33223(12) 0.0219(4) Uani 1 1 d . . . . .
H12A H 0.288067 0.374362 0.329908 0.026 Uiso 1 1 calc R U . . .
H12B H 0.329273 0.189683 0.363496 0.026 Uiso 1 1 calc R U . . .
C11 C 0.5000(3) 0.2683(2) 0.23102(12) 0.0188(3) Uani 1 1 d . . . . .
H11A H 0.481392 0.171261 0.221221 0.023 Uiso 1 1 calc R U . . .
H11B H 0.408035 0.356247 0.184800 0.023 Uiso 1 1 calc R U . . .
C16 C 1.1800(3) 0.2856(2) 0.00489(13) 0.0283(4) Uani 1 1 d . . . . .
H16A H 1.086459 0.362995 -0.044600 0.042 Uiso 1 1 calc R U . . .
H16B H 1.189660 0.182058 -0.001114 0.042 Uiso 1 1 calc R U . . .
H16C H 1.339055 0.303761 -0.001549 0.042 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 1.4934(12) . ?
S1 N1 1.6662(14) . ?
S1 C7 1.8276(16) . ?
O3 C15 1.335(2) . ?
O3 C16 1.446(2) . ?
O2 C15 1.202(2) . ?
N1 H1 0.8800 . ?
N1 C1 1.422(2) . ?
C7 C13 1.530(2) . ?
C7 C8 1.532(2) . ?
C7 C12 1.536(2) . ?
C10 C14 1.542(2) . ?
C10 C15 1.512(2) . ?
C10 C9 1.546(2) . ?
C10 C11 1.530(2) . ?
C1 C6 1.397(2) . ?
C1 C2 1.395(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.547(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C6 H6 0.9500 . ?
C6 C5 1.389(2) . ?
C4 H4 0.9500 . ?
C4 C3 1.386(3) . ?
C4 C5 1.392(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.393(2) . ?
C3 H3 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C8 1.546(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C5 H5 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C11 1.545(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 N1 110.88(7) . . ?
O1 S1 C7 106.41(7) . . ?
N1 S1 C7 98.31(7) . . ?
C15 O3 C16 116.17(13) . . ?
S1 N1 H1 120.3 . . ?
C1 N1 S1 119.35(11) . . ?
C1 N1 H1 120.3 . . ?
C13 C7 S1 114.24(11) . . ?
C13 C7 C8 109.17(13) . . ?
C13 C7 C12 109.75(13) . . ?
C8 C7 S1 109.59(11) . . ?
C8 C7 C12 109.48(13) . . ?
C12 C7 S1 104.47(10) . . ?
C14 C10 C9 108.80(13) . . ?
C15 C10 C14 112.65(14) . . ?
C15 C10 C9 107.74(13) . . ?
C15 C10 C11 110.24(13) . . ?
C11 C10 C14 108.41(13) . . ?
C11 C10 C9 108.93(13) . . ?
C6 C1 N1 117.23(14) . . ?
C2 C1 N1 123.35(15) . . ?
C2 C1 C6 119.42(15) . . ?
C7 C13 H13A 109.9 . . ?
C7 C13 H13B 109.9 . . ?
C7 C13 C14 109.15(13) . . ?
H13A C13 H13B 108.3 . . ?
C14 C13 H13A 109.9 . . ?
C14 C13 H13B 109.9 . . ?
C10 C14 C13 109.89(13) . . ?
C10 C14 H14A 109.7 . . ?
C10 C14 H14B 109.7 . . ?
C13 C14 H14A 109.7 . . ?
C13 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
O3 C15 C10 111.91(14) . . ?
O2 C15 O3 122.69(16) . . ?
O2 C15 C10 125.35(16) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 C1 119.79(16) . . ?
C5 C6 H6 120.1 . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.77(16) . . ?
C5 C4 H4 120.6 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.94(16) . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 120.95(16) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C10 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C8 C9 C10 110.48(13) . . ?
C8 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
C7 C8 C9 108.68(13) . . ?
C7 C8 H8A 110.0 . . ?
C7 C8 H8B 110.0 . . ?
C9 C8 H8A 110.0 . . ?
C9 C8 H8B 110.0 . . ?
H8A C8 H8B 108.3 . . ?
C6 C5 C4 121.13(16) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C7 C12 H12A 109.7 . . ?
C7 C12 H12B 109.7 . . ?
C7 C12 C11 109.85(13) . . ?
H12A C12 H12B 108.2 . . ?
C11 C12 H12A 109.7 . . ?
C11 C12 H12B 109.7 . . ?
C10 C11 C12 109.55(13) . . ?
C10 C11 H11A 109.8 . . ?
C10 C11 H11B 109.8 . . ?
C12 C11 H11A 109.8 . . ?
C12 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C1 C6 -170.16(12) . . . . ?
S1 N1 C1 C2 9.8(2) . . . . ?
S1 C7 C13 C14 -170.53(11) . . . . ?
S1 C7 C8 C9 177.88(11) . . . . ?
S1 C7 C12 C11 -173.34(12) . . . . ?
O1 S1 N1 C1 85.44(13) . . . . ?
O1 S1 C7 C13 65.38(13) . . . . ?
O1 S1 C7 C8 -171.77(11) . . . . ?
O1 S1 C7 C12 -54.54(12) . . . . ?
N1 S1 C7 C13 -49.35(13) . . . . ?
N1 S1 C7 C8 73.50(12) . . . . ?
N1 S1 C7 C12 -169.28(11) . . . . ?
N1 C1 C6 C5 179.99(14) . . . . ?
N1 C1 C2 C3 179.30(15) . . . . ?
C7 S1 N1 C1 -163.39(12) . . . . ?
C7 C13 C14 C10 -9.27(18) . . . . ?
C7 C12 C11 C10 -7.1(2) . . . . ?
C10 C9 C8 C7 -7.28(18) . . . . ?
C1 C6 C5 C4 0.3(3) . . . . ?
C1 C2 C3 C4 1.1(3) . . . . ?
C13 C7 C8 C9 -56.32(17) . . . . ?
C13 C7 C12 C11 63.76(18) . . . . ?
C14 C10 C15 O3 49.25(19) . . . . ?
C14 C10 C15 O2 -133.2(2) . . . . ?
C14 C10 C9 C8 62.99(17) . . . . ?
C14 C10 C11 C12 -55.25(18) . . . . ?
C15 C10 C14 C13 -172.34(13) . . . . ?
C15 C10 C9 C8 -174.60(13) . . . . ?
C15 C10 C11 C12 -178.98(14) . . . . ?
C6 C1 C2 C3 -0.8(2) . . . . ?
C2 C1 C6 C5 0.1(2) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C9 C10 C14 C13 -52.94(17) . . . . ?
C9 C10 C15 O3 -70.76(17) . . . . ?
C9 C10 C15 O2 106.8(2) . . . . ?
C9 C10 C11 C12 62.99(17) . . . . ?
C8 C7 C13 C14 66.39(17) . . . . ?
C8 C7 C12 C11 -56.04(18) . . . . ?
C5 C4 C3 C2 -0.7(3) . . . . ?
C12 C7 C13 C14 -53.61(17) . . . . ?
C12 C7 C8 C9 63.84(17) . . . . ?
C11 C10 C14 C13 65.38(17) . . . . ?
C11 C10 C15 O3 170.48(14) . . . . ?
C11 C10 C15 O2 -11.9(3) . . . . ?
C11 C10 C9 C8 -55.01(17) . . . . ?
C16 O3 C15 O2 -1.6(3) . . . . ?
C16 O3 C15 C10 176.10(14) . . . . ?

_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 2.014
_oxdiff_exptl_absorpt_empirical_full_min 0.720
####################################################################### 
# 
# 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_hpd467
_database_code_depnum_ccdc_archive 'CCDC 2170582'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman'
;The University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2022-05-04 deposited with the CCDC.	2023-10-09 downloaded from the CCDC.
;
_audit_creation_date             2021-12-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H17 N O S'
_chemical_formula_sum            'C12 H17 N O S'
_chemical_formula_weight         223.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S'
_chemical_oxdiff_usercomment     'HDC 376-CO'
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                   6.1241(2)
_cell_length_b                   8.1468(2)
_cell_length_c                   11.8684(4)
_cell_angle_alpha                95.121(3)
_cell_angle_beta                 91.181(3)
_cell_angle_gamma                105.039(3)
_cell_volume                     568.98(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5592
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      74.5790
_cell_measurement_theta_min      3.7320
_shelx_estimated_absorpt_T_max   0.871
_shelx_estimated_absorpt_T_min   0.685
_exptl_absorpt_coefficient_mu    2.298
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.491
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             240
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -5 0 0.0554
0 5 0 0.0594
-1 -5 0 0.0729
-1 2 -7 0.0188
-4 2 2 0.0863
4 -3 -2 0.0529
1 -1 7 0.0413

_exptl_crystal_size_max          0.178
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.062
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
-0.1325 -5.0060 -0.3448 0.0517 0.2050 0.9774
0.0634 5.0283 0.3854 -0.0559 -0.2221 -0.9734
-0.9537 -4.6084 0.0952 0.0082 -0.0044 1.0000
-0.9699 1.6041 -7.3341 0.9666 -0.2323 -0.1085
-3.7713 1.9468 2.2773 -0.2334 -0.9693 0.0777
3.5277 -2.9823 -2.2189 0.2309 0.9613 0.1503
0.9994 -1.4841 7.3478 -0.9690 0.2333 0.0817

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10808
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.928
_diffrn_reflns_theta_min         3.743
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -30.00  30.00   0.50    0.05    --   45.95 -19.00  60.00  120
  2  ω     83.00 119.00   0.50    0.05    --   45.95  57.00  60.00   72
  3  ω     81.00 169.00   0.50    0.05    --  106.87 146.00  29.00  176
  4  ω     96.00 178.00   0.50    0.05    --  106.87 124.00-136.00  164
  5  ω    101.00 178.00   0.50    0.05    --  106.87  77.00-180.00  154
  6  ω    101.00 178.00   0.50    0.05    --  106.87  77.00-150.00  154
  7  ω     90.00 178.00   0.50    0.05    --  106.87  45.00 -30.00  176
  8  ω     34.00  95.00   0.50    0.05    --   45.95-124.00 144.00  122
  9  ω     34.00 111.00   0.50    0.05    --  106.87-124.00 144.00  154
 10  ω     46.00 108.00   0.50    0.05    --   45.95-146.00 -21.00  124
 11  ω     46.00 127.00   0.50    0.05    --  106.87-146.00 -21.00  162
 12  ω     34.00 101.00   0.50    0.05    --  106.87 -77.00 150.00  134
 13  ω     34.00 106.00   0.50    0.05    --  106.87 -94.00  30.00  144
 14  ω     34.00 106.00   0.50    0.05    --  106.87 -94.00 -90.00  144
 15  ω     34.00  71.00   0.50    0.05    --  106.87 -61.00-150.00   74
 16  ω     34.00 106.00   0.50    0.05    --  106.87 -94.00 -60.00  144
 17  ω     34.00 101.00   0.50    0.05    --  106.87 -77.00 -60.00  134
 18  ω     34.00  71.00   0.50    0.05    --  106.87 -61.00   0.00   74
 19  ω     34.00 106.00   0.50    0.05    --  106.87 -94.00 150.00  144
 20  ω    -85.00 -12.00   0.50    0.05    --  -45.95 124.00-136.00  146
 21  ω    -51.00 -15.00   0.50    0.05    --  -88.50  45.00-180.00   72
 22  ω    -51.00 -15.00   0.50    0.05    --  -88.50  45.00-150.00   72
 23  ω    -51.00 -15.00   0.50    0.05    --  -88.50  45.00 -90.00   72
 24  ω    -51.00 -15.00   0.50    0.05    --  -88.50  45.00-120.00   72
 25  ω    -85.00 -15.00   0.50    0.05    --  -88.50 124.00-136.00  140
 26  ω    -51.00 -15.00   0.50    0.05    --  -88.50  45.00   0.00   72
 27  ω    -51.00 -15.00   0.50    0.05    --  -88.50  45.00  60.00   72
 28  ω    -51.00 -15.00   0.50    0.05    --  -88.50  45.00  90.00   72
 29  ω    -51.00 -15.00   0.50    0.05    --  -88.50  45.00 150.00   72
 30  ω   -101.00 -24.00   0.50    0.05    --  -45.95 146.00  29.00  154
 31  ω   -121.00 -28.00   0.50    0.05    --  -45.95 -37.00 150.00  186
 32  ω   -118.00 -59.00   0.50    0.05    --  -45.95-146.00 -21.00  118
 33  ω   -118.00 -83.00   0.50    0.05    --  -45.95 -57.00   0.00   70
 34  ω   -118.00 -83.00   0.50    0.05    --  -45.95 -57.00 -60.00   70
 35  ω   -118.00 -83.00   0.50    0.05    --  -45.95 -57.00-120.00   70
 36  ω   -118.00 -83.00   0.50    0.05    --  -45.95 -57.00-150.00   70
 37  ω   -121.00 -28.00   0.50    0.05    --  -45.95 -37.00 -90.00  186
 38  ω   -118.00 -83.00   0.50    0.05    --  -45.95 -57.00  90.00   70
 39  ω   -121.00 -28.00   0.50    0.05    --  -45.95 -37.00  30.00  186
 40  ω   -121.00 -73.00   0.50    0.05    --  -45.95 -37.00 -30.00   96
 41  ω   -152.00 -59.00   0.50    0.05    --  -88.50-146.00 -21.00  186
 42  ω   -118.00 -88.00   0.50    0.05    --  -45.95-125.00-180.00   60
 43  ω   -161.00 -91.00   0.50    0.05    --  -88.50 -61.00-150.00  140
 44  ω   -161.00 -91.00   0.50    0.05    --  -88.50 -61.00 -90.00  140
 45  ω   -161.00 -74.00   0.50    0.05    --  -88.50-124.00 144.00  174
 46  ω   -161.00 -91.00   0.50    0.05    --  -88.50 -61.00 150.00  140
;
_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      -0.0169575000
_diffrn_orient_matrix_UB_12      -0.0009505000
_diffrn_orient_matrix_UB_13      -0.1297572000
_diffrn_orient_matrix_UB_21      0.2278739000
_diffrn_orient_matrix_UB_22      -0.0463808000
_diffrn_orient_matrix_UB_23      -0.0086062000
_diffrn_orient_matrix_UB_31      -0.1256024000
_diffrn_orient_matrix_UB_32      -0.1912059000
_diffrn_orient_matrix_UB_33      -0.0104217000
_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                2127
_reflns_number_total             2266
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.077
_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     139
_refine_ls_number_reflns         2266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0380
_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)+(0.0500P)²+0.3500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.0985
_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:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C9(H9A,H9B), C8(H8A,H8B), C12(H12A,H12B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C4(H4), C5(H5), C3(H3)
;
_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 0.50340(6) 0.75768(4) 0.98254(3) 0.01762(14) Uani 1 1 d . . . . .
C1 C 0.7223(3) 0.66729(18) 0.80582(13) 0.0177(3) Uani 1 1 d . . . . .
O1 O 0.27929(18) 0.62649(14) 0.97337(10) 0.0208(3) Uani 1 1 d . . . . .
C7 C 0.6063(3) 0.76745(19) 1.12868(13) 0.0179(3) Uani 1 1 d . . . . .
H7 H 0.621791 0.652019 1.143603 0.022 Uiso 1 1 calc R U . . .
C6 C 0.9081(3) 0.6176(2) 0.76191(14) 0.0200(3) Uani 1 1 d . . . . .
H6 H 1.014892 0.590340 0.811222 0.024 Uiso 1 1 calc R U . . .
C10 C 0.7316(3) 0.9472(2) 1.35614(14) 0.0213(3) Uani 1 1 d . . . . .
H10A H 0.719659 1.064220 1.347042 0.026 Uiso 1 1 calc R U . . .
H10B H 0.779686 0.943683 1.435845 0.026 Uiso 1 1 calc R U . . .
N1 N 0.7035(2) 0.67859(17) 0.92479(12) 0.0189(3) Uani 1 1 d . . . . .
C9 C 0.5000(3) 0.8202(2) 1.32937(14) 0.0210(3) Uani 1 1 d . . . . .
H9A H 0.507441 0.705414 1.347492 0.025 Uiso 1 1 calc R U . . .
H9B H 0.386326 0.855107 1.377324 0.025 Uiso 1 1 calc R U . . .
C8 C 0.4264(3) 0.8118(2) 1.20462(13) 0.0190(3) Uani 1 1 d . . . . .
H8A H 0.403701 0.923313 1.188080 0.023 Uiso 1 1 calc R U . . .
H8B H 0.280810 0.724039 1.188643 0.023 Uiso 1 1 calc R U . . .
C2 C 0.5648(3) 0.70418(19) 0.73228(14) 0.0188(3) Uani 1 1 d . . . . .
H2 H 0.435333 0.734049 0.761275 0.023 Uiso 1 1 calc R U . . .
C4 C 0.7820(3) 0.6492(2) 0.57270(14) 0.0219(3) Uani 1 1 d . . . . .
H4 H 0.803355 0.644316 0.493537 0.026 Uiso 1 1 calc R U . . .
C12 C 0.8364(3) 0.8970(2) 1.15265(14) 0.0208(3) Uani 1 1 d . . . . .
H12A H 0.826254 1.010946 1.134163 0.025 Uiso 1 1 calc R U . . .
H12B H 0.950424 0.862656 1.104610 0.025 Uiso 1 1 calc R U . . .
C11 C 0.9091(3) 0.9056(2) 1.27810(14) 0.0216(3) Uani 1 1 d . . . . .
H11A H 0.934240 0.794471 1.294019 0.026 Uiso 1 1 calc R U . . .
H11B H 1.054006 0.994071 1.293987 0.026 Uiso 1 1 calc R U . . .
C5 C 0.9356(3) 0.6082(2) 0.64605(14) 0.0214(3) Uani 1 1 d . . . . .
H5 H 1.061152 0.573391 0.616345 0.026 Uiso 1 1 calc R U . . .
C3 C 0.5972(3) 0.6972(2) 0.61660(14) 0.0211(3) Uani 1 1 d . . . . .
H3 H 0.491728 0.725658 0.567089 0.025 Uiso 1 1 calc R U . . .
H1 H 0.734(3) 0.600(3) 0.9573(18) 0.025 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 O1 1.4999(11) . ?
S1 C7 1.8211(16) . ?
S1 N1 1.6587(14) . ?
C1 C6 1.398(2) . ?
C1 N1 1.416(2) . ?
C1 C2 1.395(2) . ?
C7 H7 1.0000 . ?
C7 C8 1.532(2) . ?
C7 C12 1.529(2) . ?
C6 H6 0.9500 . ?
C6 C5 1.387(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C9 1.531(2) . ?
C10 C11 1.527(2) . ?
N1 H1 0.83(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C8 1.529(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C2 H2 0.9500 . ?
C2 C3 1.390(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(2) . ?
C4 C3 1.386(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C11 1.536(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C5 H5 0.9500 . ?
C3 H3 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
O1 S1 C7 105.26(7) . . ?
O1 S1 N1 111.12(7) . . ?
N1 S1 C7 96.05(7) . . ?
C6 C1 N1 117.79(14) . . ?
C2 C1 C6 119.54(15) . . ?
C2 C1 N1 122.67(14) . . ?
S1 C7 H7 108.7 . . ?
C8 C7 S1 107.24(11) . . ?
C8 C7 H7 108.7 . . ?
C12 C7 S1 112.03(11) . . ?
C12 C7 H7 108.7 . . ?
C12 C7 C8 111.53(13) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 C1 119.69(15) . . ?
C5 C6 H6 120.2 . . ?
H10A C10 H10B 108.0 . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C11 C10 C9 111.17(13) . . ?
S1 N1 H1 115.0(14) . . ?
C1 N1 S1 119.81(11) . . ?
C1 N1 H1 115.8(14) . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C8 C9 C10 111.27(13) . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C7 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
C9 C8 C7 110.28(13) . . ?
C9 C8 H8A 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.99(15) . . ?
C3 C2 H2 120.0 . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.16(15) . . ?
C7 C12 H12A 109.7 . . ?
C7 C12 H12B 109.7 . . ?
C7 C12 C11 109.64(13) . . ?
H12A C12 H12B 108.2 . . ?
C11 C12 H12A 109.7 . . ?
C11 C12 H12B 109.7 . . ?
C10 C11 C12 111.88(14) . . ?
C10 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
C12 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C6 C5 C4 120.92(15) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.66(15) . . ?
C4 C3 H3 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 C7 C8 C9 179.32(10) . . . . ?
S1 C7 C12 C11 177.39(11) . . . . ?
C1 C6 C5 C4 0.6(2) . . . . ?
C1 C2 C3 C4 1.8(2) . . . . ?
O1 S1 C7 C8 -57.32(11) . . . . ?
O1 S1 C7 C12 180.00(10) . . . . ?
O1 S1 N1 C1 80.02(13) . . . . ?
C7 S1 N1 C1 -171.03(12) . . . . ?
C7 C12 C11 C10 -55.86(17) . . . . ?
C6 C1 N1 S1 173.11(11) . . . . ?
C6 C1 C2 C3 -2.3(2) . . . . ?
C10 C9 C8 C7 55.96(17) . . . . ?
N1 S1 C7 C8 -171.17(10) . . . . ?
N1 S1 C7 C12 66.15(12) . . . . ?
N1 C1 C6 C5 -178.69(13) . . . . ?
N1 C1 C2 C3 177.48(14) . . . . ?
C9 C10 C11 C12 55.17(18) . . . . ?
C8 C7 C12 C11 57.17(17) . . . . ?
C2 C1 C6 C5 1.1(2) . . . . ?
C2 C1 N1 S1 -6.6(2) . . . . ?
C12 C7 C8 C9 -57.68(17) . . . . ?
C11 C10 C9 C8 -54.98(18) . . . . ?
C5 C4 C3 C2 -0.2(2) . . . . ?
C3 C4 C5 C6 -1.1(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
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.216
_oxdiff_exptl_absorpt_empirical_full_min 0.770
####################################################################### 
# 
# 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_hpd528
_database_code_depnum_ccdc_archive 'CCDC 2170585'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman'
;The University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2022-05-04 deposited with the CCDC.	2023-10-09 downloaded from the CCDC.
;
_audit_creation_date             2022-03-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C35 H53 N O2 S'
_chemical_formula_sum            'C35 H53 N O2 S'
_chemical_formula_weight         551.84
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S'
_chemical_oxdiff_usercomment     'HDC 412-5'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   14.1503(2)
_cell_length_b                   19.7477(4)
_cell_length_c                   25.7609(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7198.51(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    17868
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.0980
_cell_measurement_theta_min      2.8230
_shelx_estimated_absorpt_T_max   0.947
_shelx_estimated_absorpt_T_min   0.815
_exptl_absorpt_coefficient_mu    0.993
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.521
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.018
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             2416
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-9 -4 2 0.0191
0 -2 -16 0.0712
9 4 1 0.0438
0 3 16 0.0939
-8 -6 4 0.0327
-2 12 4 0.0300
8 4 -5 0.0207
2 -12 -4 0.0412

_exptl_crystal_size_max          0.215
_exptl_crystal_size_mid          0.071
_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
-8.6913 -3.9273 1.6655 0.0497 0.1988 0.9788
0.0370 -2.4682 -16.3990 0.2262 0.9428 -0.2450
8.6404 4.2793 0.8182 -0.0836 -0.3400 -0.9367
0.1177 2.5395 16.3788 -0.2273 -0.9468 0.2277
-7.8124 -5.9500 4.1065 -0.1759 0.1327 0.9754
-2.3082 12.0636 3.8246 0.7919 -0.6083 0.0535
8.2494 4.3204 -4.7070 0.0660 -0.0482 -0.9967
2.1665 -12.1295 -3.7422 -0.7925 0.6087 -0.0365

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            38698
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.474
_diffrn_reflns_theta_min         2.819
_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 0.998
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -38.00  28.00   0.50    1.16    --  -46.87  31.00 -77.00  132
  2  ω    -30.00  29.00   0.50    1.16    --  -46.87  19.00  60.00  118
  3  ω    -81.00 -15.00   0.50    4.64    --  -88.50 101.00 117.00  132
  4  ω   -122.00 -31.00   0.50    1.16    --  -46.87 -19.00  90.00  182
  5  ω   -120.00 -87.00   0.50    1.16    --  -46.87-125.00 -90.00   66
  6  ω   -121.00 -96.00   0.50    1.16    --  -46.87 -37.00 -30.00   50
  7  ω     34.00 106.00   0.50    4.64    --  106.69-105.00 -79.00  144
  8  ω     34.00 111.00   0.50    4.64    --  106.69-125.00   0.00  154
  9  ω     34.00 101.00   0.50    4.64    --  106.69 -77.00 150.00  134
 10  ω     34.00 101.00   0.50    4.64    --  106.69 -77.00   0.00  134
 11  ω     34.00  71.00   0.50    4.64    --  106.69 -61.00 -90.00   74
 12  ω     34.00  71.00   0.50    4.64    --  106.69 -61.00-150.00   74
 13  ω     91.00 178.00   0.50    4.64    --  106.69  31.00 -77.00  174
;
_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      -0.0398840000
_diffrn_orient_matrix_UB_12      0.0655447000
_diffrn_orient_matrix_UB_13      -0.0237513000
_diffrn_orient_matrix_UB_21      -0.0160913000
_diffrn_orient_matrix_UB_22      -0.0370308000
_diffrn_orient_matrix_UB_23      -0.0519509000
_diffrn_orient_matrix_UB_31      -0.1000199000
_diffrn_orient_matrix_UB_32      -0.0203389000
_diffrn_orient_matrix_UB_33      0.0177770000
_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         0.751
_reflns_Friedel_fraction_full    0.943
_reflns_Friedel_fraction_max     0.884
_reflns_number_gt                13023
_reflns_number_total             14140
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.809
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 
;
 Flack x determined using 5064 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.100(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     721
_refine_ls_number_reflns         14140
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0698
_refine_ls_restrained_S_all      1.061
_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)+(0.0100P)²+16.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1556
_refine_ls_wR_factor_ref         0.1577
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H) groups, All O(H) groups
2. Restrained distances
 H2A-O1_$1
 1.9 with sigma of 0.02
 H2A-O2
 1.05 with sigma of 0.02
3.a Riding coordinates:
 N1(H1)
3.b Ternary CH refined with riding coordinates:
 C45(H45), C51(H51), C41(H41), C16(H16), C10(H10), C49(H49), C14(H14), C6(H6)
3.c Secondary CH2 refined with riding coordinates:
 C37(H37A,H37B), C52(H52A,H52B), C57(H57A,H57B), C38(H38A,H38B), C56(H56A,
 H56B), C53(H53A,H53B), C48(H48A,H48B), C47(H47A,H47B), C40(H40A,H40B),
 C12(H12A,H12B), C13(H13A,H13B), C17(H17A,H17B), C22(H22A,H22B), C2(H2B,H2C),
 C18(H18A,H18B), C44(H44A,H44B), C21(H21A,H21B), C9(H9A,H9B), C3(H3A,H3B),
 C5(H5A,H5B)
3.d Aromatic/amide H refined with riding coordinates:
 N2(H2), C59(H59), C24(H24), C43(H43), C63(H63), C61(H61), C25(H25), C8(H8),
 C60(H60), C62(H62), C26(H26), C28(H28), C27(H27)
3.e Idealised Me refined as rotating group:
 C69(H69A,H69B,H69C), C70(H70A,H70B,H70C), C66(H66A,H66B,H66C), C67(H67A,H67B,
 H67C), C64(H64A,H64B,H64C), C65(H65A,H65B,H65C), C68(H68A,H68B,H68C), C34(H34A,
 H34B,H34C), C35(H35A,H35B,H35C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C),
 C33(H33A,H33B,H33C), C30(H30A,H30B,H30C), C29(H29A,H29B,H29C)
3.f Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_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
S2 S 0.41797(8) 0.61454(6) 0.57190(5) 0.0248(2) Uani 1 1 d . . . . .
S1 S 0.45366(9) 0.89759(7) 0.06909(5) 0.0303(3) Uani 1 1 d . . . . .
O4 O 0.4292(3) 0.94044(17) 0.91510(12) 0.0285(7) Uani 1 1 d . . . . .
H4 H 0.453692 0.979147 0.913923 0.043 Uiso 1 1 calc R U . . .
O3 O 0.4469(3) 0.54427(17) 0.58774(15) 0.0338(8) Uani 1 1 d . . . . .
O2 O 0.4411(3) 0.56369(19) 0.41411(13) 0.0325(8) Uani 1 1 d D . . . .
O1 O 0.4218(3) 0.9690(2) 0.07047(15) 0.0405(9) Uani 1 1 d . . . . .
N2 N 0.3676(3) 0.6155(2) 0.51333(16) 0.0304(9) Uani 1 1 d . . . . .
H2 H 0.402329 0.620122 0.485209 0.036 Uiso 1 1 calc R U . . .
N1 N 0.5095(3) 0.8830(3) 0.01296(16) 0.0354(10) Uani 1 1 d . . . . .
H1 H 0.489782 0.846028 -0.001046 0.042 Uiso 1 1 d R U . . .
C46 C 0.4358(4) 0.7887(2) 0.79217(18) 0.0256(10) Uani 1 1 d . . . . .
C36 C 0.5290(3) 0.6587(2) 0.55488(17) 0.0229(9) Uani 1 1 d . . . . .
C37 C 0.5766(3) 0.6245(3) 0.50790(18) 0.0262(10) Uani 1 1 d . . . . .
H37A H 0.576718 0.574853 0.513301 0.031 Uiso 1 1 calc R U . . .
H37B H 0.538744 0.634026 0.476408 0.031 Uiso 1 1 calc R U . . .
C45 C 0.4870(4) 0.7646(2) 0.74191(18) 0.0254(10) Uani 1 1 d . . . . .
H45 H 0.540667 0.797020 0.737282 0.030 Uiso 1 1 calc R U . . .
C54 C 0.4286(4) 0.7692(3) 0.68936(19) 0.0278(10) Uani 1 1 d . . . . .
C58 C 0.2689(3) 0.6089(3) 0.50956(19) 0.0289(11) Uani 1 1 d . . . . .
C52 C 0.3314(4) 0.8624(3) 0.73541(19) 0.0292(11) Uani 1 1 d . . . . .
H52A H 0.277764 0.831778 0.742852 0.035 Uiso 1 1 calc R U . . .
H52B H 0.306050 0.908709 0.730477 0.035 Uiso 1 1 calc R U . . .
C57 C 0.5061(4) 0.7328(2) 0.54468(18) 0.0248(10) Uani 1 1 d . . . . .
H57A H 0.467129 0.736121 0.512882 0.030 Uiso 1 1 calc R U . . .
H57B H 0.565711 0.757737 0.538373 0.030 Uiso 1 1 calc R U . . .
C11 C 0.4427(4) 0.7188(3) 0.29471(19) 0.0313(11) Uani 1 1 d . . . . .
C55 C 0.5032(4) 0.7591(2) 0.64355(18) 0.0248(10) Uani 1 1 d . . . . .
C51 C 0.4004(3) 0.8620(2) 0.78129(17) 0.0240(10) Uani 1 1 d . . . . .
H51 H 0.457507 0.885992 0.767765 0.029 Uiso 1 1 calc R U . . .
C50 C 0.3687(3) 0.9058(3) 0.82933(18) 0.0259(10) Uani 1 1 d . . . . .
C38 C 0.6772(4) 0.6481(3) 0.49891(19) 0.0281(10) Uani 1 1 d . . . . .
H38A H 0.676284 0.696627 0.489245 0.034 Uiso 1 1 calc R U . . .
H38B H 0.704241 0.622590 0.469347 0.034 Uiso 1 1 calc R U . . .
C42 C 0.5502(4) 0.6897(2) 0.64997(18) 0.0263(10) Uani 1 1 d . . . . .
C56 C 0.4526(4) 0.7666(3) 0.59026(17) 0.0257(10) Uani 1 1 d . . . . .
H56A H 0.388807 0.746346 0.592821 0.031 Uiso 1 1 calc R U . . .
H56B H 0.444729 0.815382 0.582512 0.031 Uiso 1 1 calc R U . . .
C59 C 0.2303(4) 0.5681(3) 0.4713(2) 0.0349(12) Uani 1 1 d . . . . .
H59 H 0.270645 0.544466 0.448096 0.042 Uiso 1 1 calc R U . . .
C24 C 0.6564(4) 0.9166(3) -0.0293(2) 0.0352(12) Uani 1 1 d . . . . .
H24 H 0.621217 0.937390 -0.056323 0.042 Uiso 1 1 calc R U . . .
C69 C 0.3517(4) 0.7137(3) 0.6881(2) 0.0319(11) Uani 1 1 d . . . . .
H69A H 0.378372 0.670984 0.700836 0.048 Uiso 1 1 calc R U . . .
H69B H 0.329406 0.707621 0.652389 0.048 Uiso 1 1 calc R U . . .
H69C H 0.298708 0.727175 0.710270 0.048 Uiso 1 1 calc R U . . .
C53 C 0.3812(4) 0.8396(3) 0.68613(18) 0.0289(11) Uani 1 1 d . . . . .
H53A H 0.430044 0.873467 0.677153 0.035 Uiso 1 1 calc R U . . .
H53B H 0.334517 0.838877 0.657496 0.035 Uiso 1 1 calc R U . . .
C41 C 0.5918(3) 0.6525(2) 0.60372(17) 0.0222(9) Uani 1 1 d . . . . .
H41 H 0.593381 0.603358 0.613146 0.027 Uiso 1 1 calc R U . . .
C48 C 0.4803(4) 0.8320(3) 0.88362(19) 0.0302(11) Uani 1 1 d . . . . .
H48A H 0.425815 0.808691 0.899787 0.036 Uiso 1 1 calc R U . . .
H48B H 0.532538 0.833215 0.909190 0.036 Uiso 1 1 calc R U . . .
C47 C 0.5119(4) 0.7933(3) 0.83499(18) 0.0280(11) Uani 1 1 d . . . . .
H47A H 0.530365 0.746827 0.845245 0.034 Uiso 1 1 calc R U . . .
H47B H 0.568499 0.815789 0.820454 0.034 Uiso 1 1 calc R U . . .
C23 C 0.6085(4) 0.8850(3) 0.0123(2) 0.0319(11) Uani 1 1 d . . . . .
C70 C 0.5835(4) 0.8125(2) 0.6448(2) 0.0283(10) Uani 1 1 d . . . . .
H70A H 0.556176 0.857876 0.648451 0.043 Uiso 1 1 calc R U . . .
H70B H 0.619770 0.810146 0.612392 0.043 Uiso 1 1 calc R U . . .
H70C H 0.625466 0.803355 0.674216 0.043 Uiso 1 1 calc R U . . .
C39 C 0.7413(3) 0.6389(3) 0.5463(2) 0.0273(11) Uani 1 1 d . . . . .
C19 C 0.4499(4) 0.7413(3) 0.19191(19) 0.0323(11) Uani 1 1 d . . . . .
C16 C 0.4763(4) 0.6458(3) 0.28136(19) 0.0311(11) Uani 1 1 d . . . . .
H16 H 0.419544 0.623404 0.265896 0.037 Uiso 1 1 calc R U . . .
C40 C 0.6943(3) 0.6737(2) 0.59291(19) 0.0255(10) Uani 1 1 d . . . . .
H40A H 0.732489 0.664134 0.624256 0.031 Uiso 1 1 calc R U . . .
H40B H 0.695678 0.723231 0.587116 0.031 Uiso 1 1 calc R U . . .
C43 C 0.5630(4) 0.6635(3) 0.69742(19) 0.0298(11) Uani 1 1 d . . . . .
H43 H 0.593499 0.620704 0.699412 0.036 Uiso 1 1 calc R U . . .
C66 C 0.3556(4) 0.7413(3) 0.81106(19) 0.0356(13) Uani 1 1 d . . . . .
H66A H 0.296758 0.752759 0.793040 0.053 Uiso 1 1 calc R U . . .
H66B H 0.346860 0.746893 0.848552 0.053 Uiso 1 1 calc R U . . .
H66C H 0.372478 0.694144 0.803540 0.053 Uiso 1 1 calc R U . . .
C1 C 0.3443(4) 0.8497(3) 0.0558(2) 0.0332(12) Uani 1 1 d . . . . .
C63 C 0.2095(4) 0.6444(3) 0.5426(2) 0.0407(14) Uani 1 1 d . . . . .
H63 H 0.234873 0.673422 0.568507 0.049 Uiso 1 1 calc R U . . .
C20 C 0.3760(4) 0.7513(3) 0.1470(2) 0.0289(11) Uani 1 1 d . . . . .
C67 C 0.2759(4) 0.8826(3) 0.8553(2) 0.0323(11) Uani 1 1 d . . . . .
H67A H 0.225942 0.879557 0.829010 0.048 Uiso 1 1 calc R U . . .
H67B H 0.257515 0.915355 0.881976 0.048 Uiso 1 1 calc R U . . .
H67C H 0.285312 0.838060 0.871245 0.048 Uiso 1 1 calc R U . . .
C10 C 0.3948(4) 0.7458(3) 0.24322(19) 0.0315(12) Uani 1 1 d . . . . .
H10 H 0.339274 0.715270 0.237958 0.038 Uiso 1 1 calc R U . . .
C64 C 0.7597(4) 0.5640(3) 0.5576(2) 0.0321(11) Uani 1 1 d . . . . .
H64A H 0.699298 0.539857 0.559844 0.048 Uiso 1 1 calc R U . . .
H64B H 0.793629 0.559645 0.590574 0.048 Uiso 1 1 calc R U . . .
H64C H 0.797859 0.544517 0.529587 0.048 Uiso 1 1 calc R U . . .
C61 C 0.0728(4) 0.5949(3) 0.4994(2) 0.0427(14) Uani 1 1 d . . . . .
H61 H 0.006413 0.589402 0.496074 0.051 Uiso 1 1 calc R U . . .
C12 C 0.3639(5) 0.7128(3) 0.3357(2) 0.0438(15) Uani 1 1 d . . . . .
H12A H 0.345817 0.758739 0.347413 0.053 Uiso 1 1 calc R U . . .
H12B H 0.307647 0.691723 0.319525 0.053 Uiso 1 1 calc R U . . .
C25 C 0.7534(4) 0.9174(3) -0.0310(3) 0.0444(14) Uani 1 1 d . . . . .
H25 H 0.784259 0.938167 -0.059641 0.053 Uiso 1 1 calc R U . . .
C13 C 0.3931(4) 0.6712(3) 0.3824(2) 0.0372(13) Uani 1 1 d . . . . .
H13A H 0.446132 0.694107 0.400233 0.045 Uiso 1 1 calc R U . . .
H13B H 0.339482 0.668561 0.406981 0.045 Uiso 1 1 calc R U . . .
C8 C 0.3190(5) 0.8472(3) 0.1995(2) 0.0486(17) Uani 1 1 d . . . . .
H8 H 0.287328 0.889491 0.201688 0.058 Uiso 1 1 calc R U . . .
C49 C 0.4526(4) 0.9038(2) 0.86866(18) 0.0267(10) Uani 1 1 d . . . . .
H49 H 0.508473 0.926059 0.852169 0.032 Uiso 1 1 calc R U . . .
C7 C 0.3302(4) 0.8213(3) 0.1523(2) 0.0340(12) Uani 1 1 d . . . . .
C17 C 0.5476(4) 0.6480(4) 0.2376(2) 0.0451(15) Uani 1 1 d . . . . .
H17A H 0.575401 0.602513 0.232403 0.054 Uiso 1 1 calc R U . . .
H17B H 0.599339 0.679750 0.246494 0.054 Uiso 1 1 calc R U . . .
C22 C 0.3708(4) 0.7751(3) 0.0478(2) 0.0366(13) Uani 1 1 d . . . . .
H22A H 0.312145 0.748648 0.042518 0.044 Uiso 1 1 calc R U . . .
H22B H 0.409027 0.771216 0.015725 0.044 Uiso 1 1 calc R U . . .
C2 C 0.2958(4) 0.8799(3) 0.0091(2) 0.0383(13) Uani 1 1 d . . . . .
H2B H 0.333720 0.869870 -0.022270 0.046 Uiso 1 1 calc R U . . .
H2C H 0.293204 0.929701 0.013174 0.046 Uiso 1 1 calc R U . . .
C15 C 0.5057(4) 0.5982(3) 0.32824(18) 0.0319(12) Uani 1 1 d . . . . .
C60 C 0.1341(4) 0.5617(3) 0.4668(2) 0.0408(14) Uani 1 1 d . . . . .
H60 H 0.109149 0.533398 0.440353 0.049 Uiso 1 1 calc R U . . .
C65 C 0.8355(4) 0.6740(3) 0.5344(2) 0.0388(13) Uani 1 1 d . . . . .
H65A H 0.858882 0.658924 0.500545 0.058 Uiso 1 1 calc R U . . .
H65B H 0.881731 0.662342 0.561330 0.058 Uiso 1 1 calc R U . . .
H65C H 0.826137 0.723155 0.533882 0.058 Uiso 1 1 calc R U . . .
C18 C 0.4985(5) 0.6715(4) 0.1871(2) 0.0452(16) Uani 1 1 d . . . . .
H18A H 0.546090 0.673694 0.158967 0.054 Uiso 1 1 calc R U . . .
H18B H 0.450629 0.637396 0.177077 0.054 Uiso 1 1 calc R U . . .
C14 C 0.4229(4) 0.6006(3) 0.36752(18) 0.0295(11) Uani 1 1 d . . . . .
H14 H 0.367372 0.578685 0.350357 0.035 Uiso 1 1 calc R U . . .
C68 C 0.3554(4) 0.9794(3) 0.8112(2) 0.0325(11) Uani 1 1 d . . . . .
H68A H 0.414127 0.995733 0.795345 0.049 Uiso 1 1 calc R U . . .
H68B H 0.339489 1.007987 0.841063 0.049 Uiso 1 1 calc R U . . .
H68C H 0.304200 0.981495 0.785646 0.049 Uiso 1 1 calc R U . . .
C44 C 0.5337(5) 0.6953(3) 0.7474(2) 0.0381(13) Uani 1 1 d . . . . .
H44A H 0.590094 0.700015 0.769830 0.046 Uiso 1 1 calc R U . . .
H44B H 0.489028 0.664482 0.765238 0.046 Uiso 1 1 calc R U . . .
C34 C 0.5287(5) 0.7956(4) 0.1899(2) 0.0478(16) Uani 1 1 d . . . . .
H34A H 0.571144 0.786120 0.160777 0.072 Uiso 1 1 calc R U . . .
H34B H 0.564690 0.794720 0.222447 0.072 Uiso 1 1 calc R U . . .
H34C H 0.500177 0.840452 0.185373 0.072 Uiso 1 1 calc R U . . .
C6 C 0.2853(4) 0.8571(3) 0.1055(2) 0.0376(13) Uani 1 1 d . . . . .
H6 H 0.280925 0.906448 0.113777 0.045 Uiso 1 1 calc R U . . .
C21 C 0.4263(4) 0.7440(3) 0.0929(2) 0.0359(12) Uani 1 1 d . . . . .
H21A H 0.489032 0.766038 0.094837 0.043 Uiso 1 1 calc R U . . .
H21B H 0.436553 0.695357 0.085693 0.043 Uiso 1 1 calc R U . . .
C35 C 0.2959(5) 0.6966(3) 0.1473(2) 0.0449(15) Uani 1 1 d . . . . .
H35A H 0.321806 0.653261 0.159227 0.067 Uiso 1 1 calc R U . . .
H35B H 0.270579 0.691243 0.112114 0.067 Uiso 1 1 calc R U . . .
H35C H 0.245161 0.710930 0.170736 0.067 Uiso 1 1 calc R U . . .
C31 C 0.5215(6) 0.7651(4) 0.3151(2) 0.059(2) Uani 1 1 d . . . . .
H31A H 0.532902 0.755311 0.351824 0.089 Uiso 1 1 calc R U . . .
H31B H 0.502298 0.812468 0.311119 0.089 Uiso 1 1 calc R U . . .
H31C H 0.579473 0.756975 0.295227 0.089 Uiso 1 1 calc R U . . .
C62 C 0.1106(4) 0.6367(4) 0.5374(3) 0.0458(15) Uani 1 1 d . . . . .
H62 H 0.069527 0.660563 0.560112 0.055 Uiso 1 1 calc R U . . .
C26 C 0.8066(4) 0.8888(4) 0.0078(3) 0.0550(18) Uani 1 1 d . . . . .
H26 H 0.873638 0.891094 0.006840 0.066 Uiso 1 1 calc R U . . .
C32 C 0.6008(4) 0.6202(4) 0.3536(2) 0.0473(17) Uani 1 1 d . . . . .
H32A H 0.649311 0.624701 0.326708 0.071 Uiso 1 1 calc R U . . .
H32B H 0.620537 0.586052 0.378973 0.071 Uiso 1 1 calc R U . . .
H32C H 0.592284 0.663859 0.371171 0.071 Uiso 1 1 calc R U . . .
C9 C 0.3511(6) 0.8167(3) 0.2496(2) 0.0548(19) Uani 1 1 d . . . . .
H9A H 0.296486 0.813668 0.273448 0.066 Uiso 1 1 calc R U . . .
H9B H 0.398429 0.847106 0.265675 0.066 Uiso 1 1 calc R U . . .
C33 C 0.5159(5) 0.5270(3) 0.3084(2) 0.0491(17) Uani 1 1 d . . . . .
H33A H 0.459634 0.514720 0.288265 0.074 Uiso 1 1 calc R U . . .
H33B H 0.522807 0.495856 0.337722 0.074 Uiso 1 1 calc R U . . .
H33C H 0.571911 0.524030 0.286096 0.074 Uiso 1 1 calc R U . . .
C28 C 0.6614(5) 0.8555(4) 0.0515(3) 0.0560(19) Uani 1 1 d . . . . .
H28 H 0.631443 0.834581 0.080367 0.067 Uiso 1 1 calc R U . . .
C27 C 0.7621(5) 0.8573(4) 0.0475(3) 0.058(2) Uani 1 1 d . . . . .
H27 H 0.798955 0.835731 0.073557 0.070 Uiso 1 1 calc R U . . .
C3 C 0.1957(4) 0.8530(4) 0.0012(3) 0.0501(17) Uani 1 1 d . . . . .
H3A H 0.198708 0.804088 -0.006927 0.060 Uiso 1 1 calc R U . . .
H3B H 0.166736 0.876328 -0.028907 0.060 Uiso 1 1 calc R U . . .
C5 C 0.1822(5) 0.8302(4) 0.0955(3) 0.059(2) Uani 1 1 d . . . . .
H5A H 0.184981 0.780761 0.089466 0.071 Uiso 1 1 calc R U . . .
H5B H 0.143913 0.837969 0.127104 0.071 Uiso 1 1 calc R U . . .
C4 C 0.1324(5) 0.8636(4) 0.0493(3) 0.060(2) Uani 1 1 d . . . . .
C30 C 0.1108(6) 0.9358(5) 0.0569(3) 0.073(3) Uani 1 1 d . . . . .
H30A H 0.166156 0.958809 0.071502 0.109 Uiso 1 1 calc R U . . .
H30B H 0.057313 0.940430 0.080791 0.109 Uiso 1 1 calc R U . . .
H30C H 0.094595 0.956397 0.023432 0.109 Uiso 1 1 calc R U . . .
C29 C 0.0394(5) 0.8242(4) 0.0404(3) 0.066(2) Uani 1 1 d . . . . .
H29A H 0.010059 0.839404 0.007943 0.099 Uiso 1 1 calc R U . . .
H29B H -0.003844 0.832499 0.069367 0.099 Uiso 1 1 calc R U . . .
H29C H 0.053106 0.775608 0.038084 0.099 Uiso 1 1 calc R U . . .
H2A H 0.501(4) 0.548(3) 0.436(3) 0.099 Uiso 1 1 d 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
S2 O3 1.503(4) . ?
S2 N2 1.669(4) . ?
S2 C36 1.850(5) . ?
S1 O1 1.481(4) . ?
S1 N1 1.673(5) . ?
S1 C1 1.845(6) . ?
O4 H4 0.8400 . ?
O4 C49 1.437(5) . ?
O2 C14 1.427(6) . ?
O2 H2A 1.06(3) . ?
N2 H2 0.8800 . ?
N2 C58 1.407(6) . ?
N1 H1 0.8603 . ?
N1 C23 1.401(7) . ?
C46 C45 1.558(7) . ?
C46 C51 1.557(7) . ?
C46 C47 1.544(7) . ?
C46 C66 1.550(7) . ?
C36 C37 1.541(6) . ?
C36 C57 1.522(7) . ?
C36 C41 1.545(6) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C37 C38 1.516(7) . ?
C45 H45 1.0000 . ?
C45 C54 1.589(7) . ?
C45 C44 1.526(7) . ?
C54 C55 1.596(7) . ?
C54 C69 1.545(7) . ?
C54 C53 1.544(7) . ?
C58 C59 1.384(8) . ?
C58 C63 1.387(8) . ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?
C52 C51 1.533(7) . ?
C52 C53 1.520(7) . ?
C57 H57A 0.9900 . ?
C57 H57B 0.9900 . ?
C57 C56 1.549(6) . ?
C11 C16 1.556(7) . ?
C11 C10 1.582(7) . ?
C11 C12 1.541(8) . ?
C11 C31 1.534(9) . ?
C55 C42 1.533(7) . ?
C55 C56 1.555(6) . ?
C55 C70 1.552(7) . ?
C51 H51 1.0000 . ?
C51 C50 1.576(6) . ?
C50 C67 1.543(7) . ?
C50 C49 1.561(7) . ?
C50 C68 1.538(7) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C38 C39 1.531(7) . ?
C42 C41 1.519(6) . ?
C42 C43 1.340(7) . ?
C56 H56A 0.9900 . ?
C56 H56B 0.9900 . ?
C59 H59 0.9500 . ?
C59 C60 1.372(8) . ?
C24 H24 0.9500 . ?
C24 C23 1.414(8) . ?
C24 C25 1.372(8) . ?
C69 H69A 0.9800 . ?
C69 H69B 0.9800 . ?
C69 H69C 0.9800 . ?
C53 H53A 0.9900 . ?
C53 H53B 0.9900 . ?
C41 H41 1.0000 . ?
C41 C40 1.535(7) . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C48 C47 1.534(7) . ?
C48 C49 1.520(7) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C23 C28 1.385(8) . ?
C70 H70A 0.9800 . ?
C70 H70B 0.9800 . ?
C70 H70C 0.9800 . ?
C39 C40 1.535(7) . ?
C39 C64 1.529(7) . ?
C39 C65 1.534(7) . ?
C19 C20 1.573(7) . ?
C19 C10 1.537(7) . ?
C19 C18 1.544(8) . ?
C19 C34 1.549(8) . ?
C16 H16 1.0000 . ?
C16 C17 1.514(7) . ?
C16 C15 1.586(7) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C43 H43 0.9500 . ?
C43 C44 1.492(7) . ?
C66 H66A 0.9800 . ?
C66 H66B 0.9800 . ?
C66 H66C 0.9800 . ?
C1 C22 1.533(8) . ?
C1 C2 1.509(7) . ?
C1 C6 1.534(7) . ?
C63 H63 0.9500 . ?
C63 C62 1.413(8) . ?
C20 C7 1.533(7) . ?
C20 C21 1.570(7) . ?
C20 C35 1.566(8) . ?
C67 H67A 0.9800 . ?
C67 H67B 0.9800 . ?
C67 H67C 0.9800 . ?
C10 H10 1.0000 . ?
C10 C9 1.540(8) . ?
C64 H64A 0.9800 . ?
C64 H64B 0.9800 . ?
C64 H64C 0.9800 . ?
C61 H61 0.9500 . ?
C61 C60 1.374(9) . ?
C61 C62 1.387(9) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.513(8) . ?
C25 H25 0.9500 . ?
C25 C26 1.375(10) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.506(7) . ?
C8 H8 0.9500 . ?
C8 C7 1.328(8) . ?
C8 C9 1.493(8) . ?
C49 H49 1.0000 . ?
C7 C6 1.536(7) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.546(8) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C21 1.532(7) . ?
C2 H2B 0.9900 . ?
C2 H2C 0.9900 . ?
C2 C3 1.526(8) . ?
C15 C14 1.548(7) . ?
C15 C32 1.558(8) . ?
C15 C33 1.503(8) . ?
C60 H60 0.9500 . ?
C65 H65A 0.9800 . ?
C65 H65B 0.9800 . ?
C65 H65C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C14 H14 1.0000 . ?
C68 H68A 0.9800 . ?
C68 H68B 0.9800 . ?
C68 H68C 0.9800 . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C6 H6 1.0000 . ?
C6 C5 1.574(9) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C62 H62 0.9500 . ?
C26 H26 0.9500 . ?
C26 C27 1.352(10) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C28 H28 0.9500 . ?
C28 C27 1.430(9) . ?
C27 H27 0.9500 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.543(10) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C4 1.531(9) . ?
C4 C30 1.472(11) . ?
C4 C29 1.547(10) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 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
O3 S2 N2 111.9(2) . . ?
O3 S2 C36 105.5(2) . . ?
N2 S2 C36 98.2(2) . . ?
O1 S1 N1 109.2(2) . . ?
O1 S1 C1 103.7(2) . . ?
N1 S1 C1 98.5(2) . . ?
C49 O4 H4 109.5 . . ?
C14 O2 H2A 137(5) . . ?
S2 N2 H2 120.5 . . ?
C58 N2 S2 119.0(3) . . ?
C58 N2 H2 120.5 . . ?
S1 N1 H1 110.8 . . ?
C23 N1 S1 118.5(4) . . ?
C23 N1 H1 110.1 . . ?
C51 C46 C45 106.5(4) . . ?
C47 C46 C45 106.7(4) . . ?
C47 C46 C51 107.4(4) . . ?
C47 C46 C66 108.8(4) . . ?
C66 C46 C45 114.7(4) . . ?
C66 C46 C51 112.5(4) . . ?
C37 C36 S2 110.5(3) . . ?
C37 C36 C41 110.7(4) . . ?
C57 C36 S2 108.2(3) . . ?
C57 C36 C37 112.3(4) . . ?
C57 C36 C41 109.8(4) . . ?
C41 C36 S2 105.0(3) . . ?
C36 C37 H37A 108.9 . . ?
C36 C37 H37B 108.9 . . ?
H37A C37 H37B 107.7 . . ?
C38 C37 C36 113.3(4) . . ?
C38 C37 H37A 108.9 . . ?
C38 C37 H37B 108.9 . . ?
C46 C45 H45 104.9 . . ?
C46 C45 C54 116.6(4) . . ?
C54 C45 H45 104.9 . . ?
C44 C45 C46 113.4(4) . . ?
C44 C45 H45 104.9 . . ?
C44 C45 C54 110.8(4) . . ?
C45 C54 C55 106.2(4) . . ?
C69 C54 C45 110.1(4) . . ?
C69 C54 C55 111.2(4) . . ?
C53 C54 C45 108.9(4) . . ?
C53 C54 C55 111.1(4) . . ?
C53 C54 C69 109.4(4) . . ?
C59 C58 N2 119.7(5) . . ?
C59 C58 C63 119.5(5) . . ?
C63 C58 N2 120.8(5) . . ?
H52A C52 H52B 108.1 . . ?
C51 C52 H52A 109.6 . . ?
C51 C52 H52B 109.6 . . ?
C53 C52 H52A 109.6 . . ?
C53 C52 H52B 109.6 . . ?
C53 C52 C51 110.3(4) . . ?
C36 C57 H57A 109.0 . . ?
C36 C57 H57B 109.0 . . ?
C36 C57 C56 112.8(4) . . ?
H57A C57 H57B 107.8 . . ?
C56 C57 H57A 109.0 . . ?
C56 C57 H57B 109.0 . . ?
C16 C11 C10 105.0(4) . . ?
C12 C11 C16 107.6(4) . . ?
C12 C11 C10 106.9(4) . . ?
C31 C11 C16 113.9(5) . . ?
C31 C11 C10 113.4(5) . . ?
C31 C11 C12 109.7(5) . . ?
C42 C55 C54 108.6(4) . . ?
C42 C55 C56 112.3(4) . . ?
C42 C55 C70 106.7(4) . . ?
C56 C55 C54 109.7(4) . . ?
C70 C55 C54 112.6(4) . . ?
C70 C55 C56 106.9(4) . . ?
C46 C51 H51 104.1 . . ?
C46 C51 C50 117.5(4) . . ?
C52 C51 C46 110.4(4) . . ?
C52 C51 H51 104.1 . . ?
C52 C51 C50 114.9(4) . . ?
C50 C51 H51 104.1 . . ?
C67 C50 C51 114.7(4) . . ?
C67 C50 C49 111.0(4) . . ?
C49 C50 C51 106.2(4) . . ?
C68 C50 C51 108.4(4) . . ?
C68 C50 C67 108.0(4) . . ?
C68 C50 C49 108.3(4) . . ?
C37 C38 H38A 108.9 . . ?
C37 C38 H38B 108.9 . . ?
C37 C38 C39 113.4(4) . . ?
H38A C38 H38B 107.7 . . ?
C39 C38 H38A 108.9 . . ?
C39 C38 H38B 108.9 . . ?
C41 C42 C55 121.1(4) . . ?
C43 C42 C55 120.2(4) . . ?
C43 C42 C41 118.4(4) . . ?
C57 C56 C55 113.8(4) . . ?
C57 C56 H56A 108.8 . . ?
C57 C56 H56B 108.8 . . ?
C55 C56 H56A 108.8 . . ?
C55 C56 H56B 108.8 . . ?
H56A C56 H56B 107.7 . . ?
C58 C59 H59 119.8 . . ?
C60 C59 C58 120.4(6) . . ?
C60 C59 H59 119.8 . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C25 C24 C23 120.6(5) . . ?
C54 C69 H69A 109.5 . . ?
C54 C69 H69B 109.5 . . ?
C54 C69 H69C 109.5 . . ?
H69A C69 H69B 109.5 . . ?
H69A C69 H69C 109.5 . . ?
H69B C69 H69C 109.5 . . ?
C54 C53 H53A 108.5 . . ?
C54 C53 H53B 108.5 . . ?
C52 C53 C54 115.0(4) . . ?
C52 C53 H53A 108.5 . . ?
C52 C53 H53B 108.5 . . ?
H53A C53 H53B 107.5 . . ?
C36 C41 H41 106.7 . . ?
C42 C41 C36 112.2(4) . . ?
C42 C41 H41 106.7 . . ?
C42 C41 C40 112.1(4) . . ?
C40 C41 C36 111.9(4) . . ?
C40 C41 H41 106.7 . . ?
H48A C48 H48B 108.2 . . ?
C47 C48 H48A 109.8 . . ?
C47 C48 H48B 109.8 . . ?
C49 C48 H48A 109.8 . . ?
C49 C48 H48B 109.8 . . ?
C49 C48 C47 109.4(4) . . ?
C46 C47 H47A 108.7 . . ?
C46 C47 H47B 108.7 . . ?
C48 C47 C46 114.2(4) . . ?
C48 C47 H47A 108.7 . . ?
C48 C47 H47B 108.7 . . ?
H47A C47 H47B 107.6 . . ?
N1 C23 C24 120.0(5) . . ?
C28 C23 N1 121.3(5) . . ?
C28 C23 C24 118.6(5) . . ?
C55 C70 H70A 109.5 . . ?
C55 C70 H70B 109.5 . . ?
C55 C70 H70C 109.5 . . ?
H70A C70 H70B 109.5 . . ?
H70A C70 H70C 109.5 . . ?
H70B C70 H70C 109.5 . . ?
C38 C39 C40 108.3(4) . . ?
C38 C39 C65 107.6(4) . . ?
C64 C39 C38 111.6(4) . . ?
C64 C39 C40 111.0(4) . . ?
C64 C39 C65 109.1(4) . . ?
C65 C39 C40 109.2(4) . . ?
C10 C19 C20 106.8(4) . . ?
C10 C19 C18 110.3(4) . . ?
C10 C19 C34 110.7(5) . . ?
C18 C19 C20 110.5(4) . . ?
C18 C19 C34 107.1(5) . . ?
C34 C19 C20 111.5(4) . . ?
C11 C16 H16 104.6 . . ?
C11 C16 C15 117.4(4) . . ?
C17 C16 C11 110.0(5) . . ?
C17 C16 H16 104.6 . . ?
C17 C16 C15 114.2(4) . . ?
C15 C16 H16 104.6 . . ?
C41 C40 C39 115.4(4) . . ?
C41 C40 H40A 108.4 . . ?
C41 C40 H40B 108.4 . . ?
C39 C40 H40A 108.4 . . ?
C39 C40 H40B 108.4 . . ?
H40A C40 H40B 107.5 . . ?
C42 C43 H43 117.0 . . ?
C42 C43 C44 125.9(5) . . ?
C44 C43 H43 117.0 . . ?
C46 C66 H66A 109.5 . . ?
C46 C66 H66B 109.5 . . ?
C46 C66 H66C 109.5 . . ?
H66A C66 H66B 109.5 . . ?
H66A C66 H66C 109.5 . . ?
H66B C66 H66C 109.5 . . ?
C22 C1 S1 108.2(4) . . ?
C22 C1 C6 109.7(5) . . ?
C2 C1 S1 109.1(4) . . ?
C2 C1 C22 112.5(5) . . ?
C2 C1 C6 112.3(5) . . ?
C6 C1 S1 104.6(4) . . ?
C58 C63 H63 120.4 . . ?
C58 C63 C62 119.1(6) . . ?
C62 C63 H63 120.4 . . ?
C7 C20 C19 109.2(4) . . ?
C7 C20 C21 110.8(4) . . ?
C7 C20 C35 108.4(5) . . ?
C21 C20 C19 109.9(4) . . ?
C35 C20 C19 113.0(4) . . ?
C35 C20 C21 105.6(5) . . ?
C50 C67 H67A 109.5 . . ?
C50 C67 H67B 109.5 . . ?
C50 C67 H67C 109.5 . . ?
H67A C67 H67B 109.5 . . ?
H67A C67 H67C 109.5 . . ?
H67B C67 H67C 109.5 . . ?
C11 C10 H10 104.3 . . ?
C19 C10 C11 119.0(4) . . ?
C19 C10 H10 104.3 . . ?
C19 C10 C9 110.4(5) . . ?
C9 C10 C11 113.0(5) . . ?
C9 C10 H10 104.3 . . ?
C39 C64 H64A 109.5 . . ?
C39 C64 H64B 109.5 . . ?
C39 C64 H64C 109.5 . . ?
H64A C64 H64B 109.5 . . ?
H64A C64 H64C 109.5 . . ?
H64B C64 H64C 109.5 . . ?
C60 C61 H61 120.9 . . ?
C60 C61 C62 118.1(5) . . ?
C62 C61 H61 120.9 . . ?
C11 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C13 C12 C11 112.9(5) . . ?
C13 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C24 C25 H25 119.4 . . ?
C24 C25 C26 121.3(6) . . ?
C26 C25 H25 119.4 . . ?
C12 C13 H13A 109.2 . . ?
C12 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 C12 112.2(4) . . ?
C14 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
C7 C8 H8 116.6 . . ?
C7 C8 C9 126.8(5) . . ?
C9 C8 H8 116.6 . . ?
O4 C49 C50 110.6(4) . . ?
O4 C49 C48 108.6(4) . . ?
O4 C49 H49 108.3 . . ?
C50 C49 H49 108.3 . . ?
C48 C49 C50 112.7(4) . . ?
C48 C49 H49 108.3 . . ?
C20 C7 C6 121.2(5) . . ?
C8 C7 C20 118.7(5) . . ?
C8 C7 C6 119.6(5) . . ?
C16 C17 H17A 109.7 . . ?
C16 C17 H17B 109.7 . . ?
C16 C17 C18 109.6(5) . . ?
H17A C17 H17B 108.2 . . ?
C18 C17 H17A 109.7 . . ?
C18 C17 H17B 109.7 . . ?
C1 C22 H22A 108.7 . . ?
C1 C22 H22B 108.7 . . ?
H22A C22 H22B 107.6 . . ?
C21 C22 C1 114.0(5) . . ?
C21 C22 H22A 108.7 . . ?
C21 C22 H22B 108.7 . . ?
C1 C2 H2B 109.0 . . ?
C1 C2 H2C 109.0 . . ?
C1 C2 C3 113.1(5) . . ?
H2B C2 H2C 107.8 . . ?
C3 C2 H2B 109.0 . . ?
C3 C2 H2C 109.0 . . ?
C14 C15 C16 106.4(4) . . ?
C14 C15 C32 111.7(4) . . ?
C32 C15 C16 112.3(5) . . ?
C33 C15 C16 108.7(4) . . ?
C33 C15 C14 108.9(5) . . ?
C33 C15 C32 108.7(5) . . ?
C59 C60 C61 122.0(6) . . ?
C59 C60 H60 119.0 . . ?
C61 C60 H60 119.0 . . ?
C39 C65 H65A 109.5 . . ?
C39 C65 H65B 109.5 . . ?
C39 C65 H65C 109.5 . . ?
H65A C65 H65B 109.5 . . ?
H65A C65 H65C 109.5 . . ?
H65B C65 H65C 109.5 . . ?
C19 C18 C17 113.6(5) . . ?
C19 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
C17 C18 H18A 108.8 . . ?
C17 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
O2 C14 C13 108.0(4) . . ?
O2 C14 C15 113.4(4) . . ?
O2 C14 H14 107.0 . . ?
C13 C14 C15 114.0(5) . . ?
C13 C14 H14 107.0 . . ?
C15 C14 H14 107.0 . . ?
C50 C68 H68A 109.5 . . ?
C50 C68 H68B 109.5 . . ?
C50 C68 H68C 109.5 . . ?
H68A C68 H68B 109.5 . . ?
H68A C68 H68C 109.5 . . ?
H68B C68 H68C 109.5 . . ?
C45 C44 H44A 108.6 . . ?
C45 C44 H44B 108.6 . . ?
C43 C44 C45 114.7(4) . . ?
C43 C44 H44A 108.6 . . ?
C43 C44 H44B 108.6 . . ?
H44A C44 H44B 107.6 . . ?
C19 C34 H34A 109.5 . . ?
C19 C34 H34B 109.5 . . ?
C19 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C1 C6 C7 112.7(5) . . ?
C1 C6 H6 107.8 . . ?
C1 C6 C5 109.7(5) . . ?
C7 C6 H6 107.8 . . ?
C7 C6 C5 110.9(5) . . ?
C5 C6 H6 107.8 . . ?
C20 C21 H21A 108.8 . . ?
C20 C21 H21B 108.8 . . ?
C22 C21 C20 113.8(5) . . ?
C22 C21 H21A 108.8 . . ?
C22 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
C20 C35 H35A 109.5 . . ?
C20 C35 H35B 109.5 . . ?
C20 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C11 C31 H31A 109.5 . . ?
C11 C31 H31B 109.5 . . ?
C11 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C63 C62 H62 119.6 . . ?
C61 C62 C63 120.8(6) . . ?
C61 C62 H62 119.6 . . ?
C25 C26 H26 120.5 . . ?
C27 C26 C25 119.0(6) . . ?
C27 C26 H26 120.5 . . ?
C15 C32 H32A 109.5 . . ?
C15 C32 H32B 109.5 . . ?
C15 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C10 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C8 C9 C10 113.4(5) . . ?
C8 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C15 C33 H33A 109.5 . . ?
C15 C33 H33B 109.5 . . ?
C15 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C23 C28 H28 120.8 . . ?
C23 C28 C27 118.4(6) . . ?
C27 C28 H28 120.8 . . ?
C26 C27 C28 122.0(6) . . ?
C26 C27 H27 119.0 . . ?
C28 C27 H27 119.0 . . ?
C2 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
C2 C3 C4 112.6(6) . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C6 C5 H5A 108.7 . . ?
C6 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C4 C5 C6 114.1(5) . . ?
C4 C5 H5A 108.7 . . ?
C4 C5 H5B 108.7 . . ?
C3 C4 C29 107.8(7) . . ?
C5 C4 C3 107.4(6) . . ?
C5 C4 C29 106.9(6) . . ?
C30 C4 C3 111.0(6) . . ?
C30 C4 C5 114.2(8) . . ?
C30 C4 C29 109.3(7) . . ?
C4 C30 H30A 109.5 . . ?
C4 C30 H30B 109.5 . . ?
C4 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C4 C29 H29A 109.5 . . ?
C4 C29 H29B 109.5 . . ?
C4 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 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
S2 N2 C58 C59 -138.0(4) . . . . ?
S2 N2 C58 C63 44.0(7) . . . . ?
S2 C36 C37 C38 -167.7(3) . . . . ?
S2 C36 C57 C56 54.1(5) . . . . ?
S2 C36 C41 C42 -64.5(4) . . . . ?
S2 C36 C41 C40 168.4(3) . . . . ?
S1 N1 C23 C24 -138.2(5) . . . . ?
S1 N1 C23 C28 42.9(8) . . . . ?
S1 C1 C22 C21 55.4(6) . . . . ?
S1 C1 C2 C3 -168.8(5) . . . . ?
S1 C1 C6 C7 -66.7(5) . . . . ?
S1 C1 C6 C5 169.3(4) . . . . ?
O3 S2 N2 C58 91.6(4) . . . . ?
O3 S2 C36 C37 63.4(4) . . . . ?
O3 S2 C36 C57 -173.3(3) . . . . ?
O3 S2 C36 C41 -56.0(3) . . . . ?
O1 S1 N1 C23 98.3(5) . . . . ?
O1 S1 C1 C22 174.0(3) . . . . ?
O1 S1 C1 C2 51.3(4) . . . . ?
O1 S1 C1 C6 -69.0(4) . . . . ?
N2 S2 C36 C37 -52.1(4) . . . . ?
N2 S2 C36 C57 71.2(3) . . . . ?
N2 S2 C36 C41 -171.5(3) . . . . ?
N2 C58 C59 C60 -179.3(5) . . . . ?
N2 C58 C63 C62 179.5(5) . . . . ?
N1 S1 C1 C22 61.8(4) . . . . ?
N1 S1 C1 C2 -60.9(4) . . . . ?
N1 S1 C1 C6 178.7(4) . . . . ?
N1 C23 C28 C27 177.8(6) . . . . ?
C46 C45 C54 C55 166.7(4) . . . . ?
C46 C45 C54 C69 -72.9(5) . . . . ?
C46 C45 C54 C53 47.0(6) . . . . ?
C46 C45 C44 C43 166.1(5) . . . . ?
C46 C51 C50 C67 -70.2(6) . . . . ?
C46 C51 C50 C49 52.8(5) . . . . ?
C46 C51 C50 C68 169.1(4) . . . . ?
C36 S2 N2 C58 -158.0(4) . . . . ?
C36 C37 C38 C39 55.9(6) . . . . ?
C36 C57 C56 C55 53.8(6) . . . . ?
C36 C41 C40 C39 -52.3(6) . . . . ?
C37 C36 C57 C56 176.4(4) . . . . ?
C37 C36 C41 C42 176.2(4) . . . . ?
C37 C36 C41 C40 49.1(5) . . . . ?
C37 C38 C39 C40 -53.9(5) . . . . ?
C37 C38 C39 C64 68.5(5) . . . . ?
C37 C38 C39 C65 -171.9(4) . . . . ?
C45 C46 C51 C52 60.5(5) . . . . ?
C45 C46 C51 C50 -165.0(4) . . . . ?
C45 C46 C47 C48 166.2(4) . . . . ?
C45 C54 C55 C42 59.8(5) . . . . ?
C45 C54 C55 C56 -177.1(4) . . . . ?
C45 C54 C55 C70 -58.2(5) . . . . ?
C45 C54 C53 C52 -46.5(6) . . . . ?
C54 C45 C44 C43 32.6(7) . . . . ?
C54 C55 C42 C41 154.5(4) . . . . ?
C54 C55 C42 C43 -31.6(6) . . . . ?
C54 C55 C56 C57 -158.6(4) . . . . ?
C58 C59 C60 C61 0.1(9) . . . . ?
C58 C63 C62 C61 -0.6(10) . . . . ?
C52 C51 C50 C67 62.3(6) . . . . ?
C52 C51 C50 C49 -174.7(4) . . . . ?
C52 C51 C50 C68 -58.4(6) . . . . ?
C57 C36 C37 C38 71.3(5) . . . . ?
C57 C36 C41 C42 51.6(5) . . . . ?
C57 C36 C41 C40 -75.4(5) . . . . ?
C11 C16 C17 C18 -67.1(7) . . . . ?
C11 C16 C15 C14 51.2(6) . . . . ?
C11 C16 C15 C32 -71.3(6) . . . . ?
C11 C16 C15 C33 168.3(5) . . . . ?
C11 C10 C9 C8 171.1(6) . . . . ?
C11 C12 C13 C14 -58.0(7) . . . . ?
C55 C54 C53 C52 -163.0(4) . . . . ?
C55 C42 C41 C36 -40.4(6) . . . . ?
C55 C42 C41 C40 86.5(5) . . . . ?
C55 C42 C43 C44 1.2(9) . . . . ?
C51 C46 C45 C54 -54.2(5) . . . . ?
C51 C46 C45 C44 175.2(4) . . . . ?
C51 C46 C47 C48 52.3(6) . . . . ?
C51 C52 C53 C54 56.4(6) . . . . ?
C51 C50 C49 O4 -177.8(4) . . . . ?
C51 C50 C49 C48 -56.1(5) . . . . ?
C38 C39 C40 C41 53.0(6) . . . . ?
C42 C55 C56 C57 -37.7(6) . . . . ?
C42 C41 C40 C39 -179.4(4) . . . . ?
C42 C43 C44 C45 -1.3(9) . . . . ?
C56 C55 C42 C41 33.0(6) . . . . ?
C56 C55 C42 C43 -153.1(5) . . . . ?
C59 C58 C63 C62 1.6(9) . . . . ?
C24 C23 C28 C27 -1.1(11) . . . . ?
C24 C25 C26 C27 2.2(11) . . . . ?
C69 C54 C55 C42 -59.9(5) . . . . ?
C69 C54 C55 C56 63.2(5) . . . . ?
C69 C54 C55 C70 -177.9(4) . . . . ?
C69 C54 C53 C52 73.9(5) . . . . ?
C53 C54 C55 C42 178.0(4) . . . . ?
C53 C54 C55 C56 -58.9(5) . . . . ?
C53 C54 C55 C70 60.0(5) . . . . ?
C53 C52 C51 C46 -63.2(5) . . . . ?
C53 C52 C51 C50 161.1(4) . . . . ?
C41 C36 C37 C38 -51.8(5) . . . . ?
C41 C36 C57 C56 -60.0(5) . . . . ?
C41 C42 C43 C44 175.2(5) . . . . ?
C47 C46 C45 C54 -168.6(4) . . . . ?
C47 C46 C45 C44 60.8(6) . . . . ?
C47 C46 C51 C52 174.5(4) . . . . ?
C47 C46 C51 C50 -51.0(6) . . . . ?
C47 C48 C49 O4 -176.3(4) . . . . ?
C47 C48 C49 C50 60.8(6) . . . . ?
C23 C24 C25 C26 -1.1(10) . . . . ?
C23 C28 C27 C26 2.3(13) . . . . ?
C70 C55 C42 C41 -83.8(5) . . . . ?
C70 C55 C42 C43 90.1(6) . . . . ?
C70 C55 C56 C57 79.0(5) . . . . ?
C19 C20 C7 C8 -31.9(7) . . . . ?
C19 C20 C7 C6 156.6(5) . . . . ?
C19 C20 C21 C22 -160.9(5) . . . . ?
C19 C10 C9 C8 35.2(8) . . . . ?
C16 C11 C10 C19 -51.7(6) . . . . ?
C16 C11 C10 C9 176.5(5) . . . . ?
C16 C11 C12 C13 53.1(6) . . . . ?
C16 C17 C18 C19 57.4(8) . . . . ?
C16 C15 C14 O2 -175.9(4) . . . . ?
C16 C15 C14 C13 -51.7(6) . . . . ?
C43 C42 C41 C36 145.6(5) . . . . ?
C43 C42 C41 C40 -87.5(6) . . . . ?
C66 C46 C45 C54 70.9(6) . . . . ?
C66 C46 C45 C44 -59.7(6) . . . . ?
C66 C46 C51 C52 -65.9(5) . . . . ?
C66 C46 C51 C50 68.6(5) . . . . ?
C66 C46 C47 C48 -69.7(5) . . . . ?
C1 S1 N1 C23 -153.8(5) . . . . ?
C1 C22 C21 C20 54.7(7) . . . . ?
C1 C2 C3 C4 56.1(8) . . . . ?
C1 C6 C5 C4 -55.0(8) . . . . ?
C63 C58 C59 C60 -1.3(8) . . . . ?
C20 C19 C10 C11 163.9(5) . . . . ?
C20 C19 C10 C9 -63.2(6) . . . . ?
C20 C19 C18 C17 -161.9(5) . . . . ?
C20 C7 C6 C1 -41.4(7) . . . . ?
C20 C7 C6 C5 82.0(7) . . . . ?
C67 C50 C49 O4 -52.5(5) . . . . ?
C67 C50 C49 C48 69.2(5) . . . . ?
C10 C11 C16 C17 61.2(6) . . . . ?
C10 C11 C16 C15 -165.9(5) . . . . ?
C10 C11 C12 C13 165.4(5) . . . . ?
C10 C19 C20 C7 60.9(5) . . . . ?
C10 C19 C20 C21 -177.4(4) . . . . ?
C10 C19 C20 C35 -59.8(6) . . . . ?
C10 C19 C18 C17 -44.1(7) . . . . ?
C64 C39 C40 C41 -69.8(5) . . . . ?
C12 C11 C16 C17 174.8(5) . . . . ?
C12 C11 C16 C15 -52.3(6) . . . . ?
C12 C11 C10 C19 -165.7(5) . . . . ?
C12 C11 C10 C9 62.5(7) . . . . ?
C12 C13 C14 O2 -175.0(5) . . . . ?
C12 C13 C14 C15 57.9(7) . . . . ?
C25 C24 C23 N1 -178.4(6) . . . . ?
C25 C24 C23 C28 0.6(9) . . . . ?
C25 C26 C27 C28 -2.9(12) . . . . ?
C8 C7 C6 C1 147.1(6) . . . . ?
C8 C7 C6 C5 -89.5(8) . . . . ?
C49 C48 C47 C46 -59.0(6) . . . . ?
C7 C20 C21 C22 -40.3(6) . . . . ?
C7 C8 C9 C10 -4.5(12) . . . . ?
C7 C6 C5 C4 179.9(6) . . . . ?
C17 C16 C15 C14 -177.9(5) . . . . ?
C17 C16 C15 C32 59.6(7) . . . . ?
C17 C16 C15 C33 -60.8(7) . . . . ?
C22 C1 C2 C3 71.1(7) . . . . ?
C22 C1 C6 C7 49.3(6) . . . . ?
C22 C1 C6 C5 -74.8(6) . . . . ?
C2 C1 C22 C21 176.0(5) . . . . ?
C2 C1 C6 C7 175.2(5) . . . . ?
C2 C1 C6 C5 51.1(7) . . . . ?
C2 C3 C4 C5 -55.7(8) . . . . ?
C2 C3 C4 C30 69.7(8) . . . . ?
C2 C3 C4 C29 -170.6(5) . . . . ?
C15 C16 C17 C18 158.4(5) . . . . ?
C60 C61 C62 C63 -0.6(10) . . . . ?
C65 C39 C40 C41 169.9(4) . . . . ?
C18 C19 C20 C7 -179.1(5) . . . . ?
C18 C19 C20 C21 -57.5(6) . . . . ?
C18 C19 C20 C35 60.2(6) . . . . ?
C18 C19 C10 C11 43.8(7) . . . . ?
C18 C19 C10 C9 176.7(5) . . . . ?
C68 C50 C49 O4 65.9(5) . . . . ?
C68 C50 C49 C48 -172.4(4) . . . . ?
C44 C45 C54 C55 -61.5(5) . . . . ?
C44 C45 C54 C69 58.9(6) . . . . ?
C44 C45 C54 C53 178.8(4) . . . . ?
C34 C19 C20 C7 -60.1(6) . . . . ?
C34 C19 C20 C21 61.6(6) . . . . ?
C34 C19 C20 C35 179.2(5) . . . . ?
C34 C19 C10 C11 -74.6(6) . . . . ?
C34 C19 C10 C9 58.3(6) . . . . ?
C34 C19 C18 C17 76.4(6) . . . . ?
C6 C1 C22 C21 -58.2(6) . . . . ?
C6 C1 C2 C3 -53.2(7) . . . . ?
C6 C5 C4 C3 56.3(9) . . . . ?
C6 C5 C4 C30 -67.2(8) . . . . ?
C6 C5 C4 C29 171.8(7) . . . . ?
C21 C20 C7 C8 -152.9(6) . . . . ?
C21 C20 C7 C6 35.5(7) . . . . ?
C35 C20 C7 C8 91.6(7) . . . . ?
C35 C20 C7 C6 -80.0(6) . . . . ?
C35 C20 C21 C22 76.9(6) . . . . ?
C31 C11 C16 C17 -63.4(6) . . . . ?
C31 C11 C16 C15 69.5(6) . . . . ?
C31 C11 C10 C19 73.3(7) . . . . ?
C31 C11 C10 C9 -58.5(7) . . . . ?
C31 C11 C12 C13 -71.4(7) . . . . ?
C62 C61 C60 C59 0.9(9) . . . . ?
C32 C15 C14 O2 -53.0(6) . . . . ?
C32 C15 C14 C13 71.2(6) . . . . ?
C9 C8 C7 C20 3.3(11) . . . . ?
C9 C8 C7 C6 175.1(7) . . . . ?
C33 C15 C14 O2 67.2(6) . . . . ?
C33 C15 C14 C13 -168.7(5) . . . . ?

_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 -0.241 -0.013 0.260 429.2 131.2 '3 CH2Cl2'
2 -0.259 0.013 0.760 429.2 131.4 '3 CH2Cl2'
3 0.241 0.487 0.240 429.2 131.0 '3 CH2Cl2'
4 0.259 0.513 0.740 429.2 131.6 '3 CH2Cl2'
5 0.153 0.780 0.903 7.1 0.0 ?
6 0.236 0.780 0.604 7.1 0.6 ?
7 0.264 0.220 0.104 7.1 0.6 ?
8 0.347 0.220 0.403 7.1 0.0 ?
9 0.653 0.720 0.097 7.1 0.0 ?
10 0.736 0.720 0.396 7.1 0.6 ?
11 0.764 0.280 0.896 7.1 0.6 ?
12 0.847 0.280 0.597 7.1 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
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.406
_oxdiff_exptl_absorpt_empirical_full_min 0.807
