# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_hpd140
_database_code_depnum_ccdc_archive 'CCDC 2042730'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman'
;University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2020-11-05 deposited with the CCDC.	2022-03-21 downloaded from the CCDC.
;
_audit_creation_date             2020-07-01
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H29 N O6 S'
_chemical_formula_sum            'C16 H29 N O6 S'
_chemical_formula_weight         363.46
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
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                   5.46991(9)
_cell_length_b                   10.15896(14)
_cell_length_c                   34.3303(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1907.69(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13332
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.7780
_cell_measurement_theta_min      2.5690
_shelx_estimated_absorpt_T_max   0.912
_shelx_estimated_absorpt_T_min   0.675
_exptl_absorpt_coefficient_mu    1.766
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.652
_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    1.265
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 -1 4 0.0977
0 -6 -10 0.0643
3 -1 -6 0.1141
0 6 10 0.0437
-3 -1 -3 0.1100
0 2 -21 0.0381
0 -2 21 0.0114

_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.053
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
-3.4688 -0.6562 4.2724 -0.0186 -0.0848 0.9962
-0.1824 -5.8312 -10.3419 0.2318 0.9631 0.1366
3.3828 -0.6307 -6.4827 0.0692 0.2948 -0.9531
0.2730 5.8388 10.2128 -0.2309 -0.9593 -0.1625
-3.4966 -0.5276 -3.3872 0.3143 -0.0100 0.9493
0.0355 1.9968 -21.2348 0.9785 -0.0256 -0.2049
0.0781 -1.9713 21.2556 -0.9846 0.0258 0.1732

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            21957
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.533
_diffrn_reflns_theta_min         2.574
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -84.00 -15.00   0.50    0.10    --  -88.50 116.00  60.00  138
  2  ω   -164.00 -72.00   0.50    0.10    --  -88.50 -18.00  62.00  184
  3  ω     34.00 109.00   0.50    0.10    --  106.69-114.00-121.00  150
  4  ω   -120.00 -87.00   0.50    0.05    --  -46.87-125.00 120.00   66
  5  ω   -120.00 -87.00   0.50    0.05    --  -46.87-125.00 -60.00   66
  6  ω    -30.00  29.00   0.50    0.05    --  -46.87  18.00-129.00  118
  7  ω   -120.00 -87.00   0.50    0.05    --  -46.87-125.00 -90.00   66
  8  ω   -120.00 -83.00   0.50    0.05    --  -46.87 -57.00-120.00   74
  9  ω    -30.00  29.00   0.50    0.05    --  -46.87  19.00   0.00  118
 10  ω     34.00 101.00   0.50    0.10    --  106.69 -77.00 120.00  134
 11  ω     34.00  71.00   0.50    0.10    --  106.69 -61.00 120.00   74
 12  ω     34.00  71.00   0.50    0.10    --  106.69 -61.00  30.00   74
 13  ω     34.00  71.00   0.50    0.10    --  106.69 -61.00-150.00   74
 14  ω     89.00 178.00   0.50    0.10    --  106.69  15.00-180.00  178
 15  ω     34.00 101.00   0.50    0.10    --  106.69 -77.00 -90.00  134
 16  ω     34.00  71.00   0.50    0.10    --  106.69 -61.00-120.00   74
 17  ω     34.00 109.00   0.50    0.10    --  106.69-116.00 -28.00  150
 18  ω   -120.00 -83.00   0.50    0.05    --  -46.87 -57.00 -90.00   74
 19  ω   -121.00 -32.00   0.50    0.05    --  -46.87 -37.00 -30.00  178
 20  ω   -120.00 -83.00   0.50    0.05    --  -46.87 -57.00 -60.00   74
 21  ω   -120.00 -83.00   0.50    0.05    --  -46.87 -57.00 -30.00   74
 22  ω   -121.00 -32.00   0.50    0.05    --  -46.87 -37.00 120.00  178
 23  ω   -161.00-104.00   0.50    0.10    --  -88.50 -45.00  30.00  114
 24  ω   -163.00 -73.00   0.50    0.10    --  -88.50 -30.00-180.00  180
 25  ω    -51.00 -16.00   0.50    0.10    --  -88.50  45.00   0.00   70
 26  ω     89.00 178.00   0.50    0.10    --  106.69  15.00   0.00  178
 27  ω     89.00 178.00   0.50    0.10    --  106.69  15.00 -90.00  178
 28  ω     34.00  71.00   0.50    0.10    --  106.69 -61.00   0.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0542604000
_diffrn_orient_matrix_UB_12      0.0375610000
_diffrn_orient_matrix_UB_13      -0.0426367000
_diffrn_orient_matrix_UB_21      0.0366031000
_diffrn_orient_matrix_UB_22      -0.1444625000
_diffrn_orient_matrix_UB_23      -0.0123186000
_diffrn_orient_matrix_UB_31      -0.2739165000
_diffrn_orient_matrix_UB_32      -0.0267054000
_diffrn_orient_matrix_UB_33      0.0066772000
_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         0.675
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.953
_reflns_number_gt                3787
_reflns_number_total             3907
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT n/a (Sheldrick, 2015)'
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 1475 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.018(8)
_refine_ls_extinction_coef       0.0010(2)
_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   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3907
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0303
_refine_ls_restrained_S_all      1.025
_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)+(0.0380P)²+0.6621P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0767
_refine_ls_wR_factor_ref         0.0773
_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:
 C4(H4A,H4B), C5(H5A,H5B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2)
2.d X=CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.e Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C14(H14A,H14B,H14C), C9(H9A,H9B,
 H9C), C11(H11A,H11B,H11C), C10(H10A,H10B,H10C)
;
_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 0.10151(10) 0.69037(5) 0.55931(2) 0.01834(13) Uani 1 1 d . . . . .
O4 O 0.3463(3) 0.70197(14) 0.69576(4) 0.0173(3) Uani 1 1 d . . . . .
O5 O 0.8583(3) 0.36432(15) 0.63479(5) 0.0235(4) Uani 1 1 d . . . . .
O3 O 0.1884(3) 0.49795(15) 0.70635(4) 0.0228(4) Uani 1 1 d . . . . .
O6 O 0.5777(3) 0.20360(15) 0.62320(5) 0.0239(3) Uani 1 1 d . . . . .
O2 O -0.1529(3) 0.66491(17) 0.55059(4) 0.0259(4) Uani 1 1 d . . . . .
O1 O 0.1798(3) 0.82549(15) 0.56087(5) 0.0283(4) Uani 1 1 d . . . . .
N1 N 0.4520(4) 0.39629(17) 0.64549(5) 0.0178(4) Uani 1 1 d . . . . .
H1 H 0.307638 0.358627 0.647490 0.021 Uiso 1 1 calc R U . . .
C7 C 0.6485(4) 0.3242(2) 0.63432(6) 0.0171(4) Uani 1 1 d . . . . .
C12 C 0.3184(4) 0.5730(2) 0.68865(6) 0.0169(4) Uani 1 1 d . . . . .
C13 C 0.2051(4) 0.7698(2) 0.72682(6) 0.0178(4) Uani 1 1 d . . . . .
C4 C 0.1639(4) 0.6126(2) 0.60477(6) 0.0186(4) Uani 1 1 d . . . . .
H4A H 0.058573 0.652795 0.624979 0.022 Uiso 1 1 calc R U . . .
H4B H 0.118537 0.518459 0.602758 0.022 Uiso 1 1 calc R U . . .
C5 C 0.4291(4) 0.6218(2) 0.61803(6) 0.0179(4) Uani 1 1 d . . . . .
H5A H 0.468161 0.714580 0.624325 0.022 Uiso 1 1 calc R U . . .
H5B H 0.537551 0.593772 0.596488 0.022 Uiso 1 1 calc R U . . .
C6 C 0.4788(4) 0.53506(19) 0.65415(6) 0.0162(4) Uani 1 1 d . . . . .
H6 H 0.652640 0.549902 0.662048 0.019 Uiso 1 1 calc R U . . .
C15 C -0.0653(5) 0.7599(2) 0.71810(7) 0.0241(5) Uani 1 1 d . . . . .
H15A H -0.096360 0.790513 0.691484 0.036 Uiso 1 1 calc R U . . .
H15B H -0.156659 0.814775 0.736531 0.036 Uiso 1 1 calc R U . . .
H15C H -0.118026 0.668150 0.720639 0.036 Uiso 1 1 calc R U . . .
C3 C 0.2809(5) 0.6066(2) 0.52400(6) 0.0227(5) Uani 1 1 d . . . . .
H3A H 0.244549 0.642995 0.497879 0.027 Uiso 1 1 calc R U . . .
H3B H 0.456167 0.622195 0.529488 0.027 Uiso 1 1 calc R U . . .
C8 C 0.7579(4) 0.1049(2) 0.60937(7) 0.0225(5) Uani 1 1 d . . . . .
C16 C 0.2924(5) 0.9112(2) 0.72342(7) 0.0228(5) Uani 1 1 d . . . . .
H16A H 0.467285 0.915570 0.729517 0.034 Uiso 1 1 calc R U . . .
H16B H 0.201333 0.966558 0.741755 0.034 Uiso 1 1 calc R U . . .
H16C H 0.265074 0.942799 0.696805 0.034 Uiso 1 1 calc R U . . .
C14 C 0.2698(5) 0.7131(2) 0.76658(6) 0.0248(5) Uani 1 1 d . . . . .
H14A H 0.212477 0.621855 0.768167 0.037 Uiso 1 1 calc R U . . .
H14B H 0.191057 0.765500 0.786996 0.037 Uiso 1 1 calc R U . . .
H14C H 0.447502 0.715435 0.770143 0.037 Uiso 1 1 calc R U . . .
C2 C 0.2328(5) 0.4615(2) 0.52380(7) 0.0289(6) Uani 1 1 d . . . . .
H2 H 0.073804 0.431568 0.517081 0.035 Uiso 1 1 calc R U . . .
C9 C 0.9108(6) 0.1579(2) 0.57577(7) 0.0322(6) Uani 1 1 d . . . . .
H9A H 0.802995 0.197782 0.556261 0.048 Uiso 1 1 calc R U . . .
H9B H 1.002628 0.085504 0.563836 0.048 Uiso 1 1 calc R U . . .
H9C H 1.025061 0.224328 0.585576 0.048 Uiso 1 1 calc R U . . .
C11 C 0.9173(6) 0.0611(2) 0.64261(7) 0.0325(6) Uani 1 1 d . . . . .
H11A H 1.020297 0.134674 0.651100 0.049 Uiso 1 1 calc R U . . .
H11B H 1.021267 -0.011958 0.634065 0.049 Uiso 1 1 calc R U . . .
H11C H 0.814396 0.032094 0.664341 0.049 Uiso 1 1 calc R U . . .
C1 C 0.4006(7) 0.3737(3) 0.53249(8) 0.0402(7) Uani 1 1 d . . . . .
H1A H 0.560986 0.401267 0.539303 0.048 Uiso 1 1 calc R U . . .
H1B H 0.361569 0.282559 0.531971 0.048 Uiso 1 1 calc R U . . .
C10 C 0.5933(6) -0.0046(2) 0.59488(10) 0.0438(7) Uani 1 1 d . . . . .
H10A H 0.492860 -0.037243 0.616460 0.066 Uiso 1 1 calc R U . . .
H10B H 0.693604 -0.076591 0.584610 0.066 Uiso 1 1 calc R U . . .
H10C H 0.486882 0.029190 0.574203 0.066 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4465(17) . ?
S1 O1 1.4390(16) . ?
S1 C4 1.782(2) . ?
S1 C3 1.777(2) . ?
O4 C12 1.342(2) . ?
O4 C13 1.486(2) . ?
O5 C7 1.218(3) . ?
O3 C12 1.207(3) . ?
O6 C7 1.340(2) . ?
O6 C8 1.484(3) . ?
N1 H1 0.8800 . ?
N1 C7 1.356(3) . ?
N1 C6 1.448(2) . ?
C12 C6 1.523(3) . ?
C13 C15 1.512(3) . ?
C13 C16 1.519(3) . ?
C13 C14 1.523(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.523(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.546(3) . ?
C6 H6 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C2 1.497(3) . ?
C8 C9 1.523(3) . ?
C8 C11 1.504(4) . ?
C8 C10 1.515(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C2 H2 0.9500 . ?
C2 C1 1.315(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C1 H1A 0.9500 . ?
C1 H1B 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 C4 106.62(10) . . ?
O2 S1 C3 107.72(11) . . ?
O1 S1 O2 117.68(10) . . ?
O1 S1 C4 109.47(10) . . ?
O1 S1 C3 108.54(11) . . ?
C3 S1 C4 106.22(11) . . ?
C12 O4 C13 121.62(17) . . ?
C7 O6 C8 121.10(18) . . ?
C7 N1 H1 119.9 . . ?
C7 N1 C6 120.22(19) . . ?
C6 N1 H1 119.9 . . ?
O5 C7 O6 125.6(2) . . ?
O5 C7 N1 124.22(19) . . ?
O6 C7 N1 110.19(19) . . ?
O4 C12 C6 108.84(17) . . ?
O3 C12 O4 126.3(2) . . ?
O3 C12 C6 124.84(19) . . ?
O4 C13 C15 109.60(17) . . ?
O4 C13 C16 102.70(17) . . ?
O4 C13 C14 110.30(17) . . ?
C15 C13 C16 110.80(19) . . ?
C15 C13 C14 112.3(2) . . ?
C16 C13 C14 110.71(19) . . ?
S1 C4 H4A 108.6 . . ?
S1 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C5 C4 S1 114.61(15) . . ?
C5 C4 H4A 108.6 . . ?
C5 C4 H4B 108.6 . . ?
C4 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C4 C5 C6 111.84(18) . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
N1 C6 C12 110.32(17) . . ?
N1 C6 C5 111.88(16) . . ?
N1 C6 H6 107.4 . . ?
C12 C6 C5 112.22(17) . . ?
C12 C6 H6 107.4 . . ?
C5 C6 H6 107.4 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
S1 C3 H3A 109.2 . . ?
S1 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C2 C3 S1 112.20(17) . . ?
C2 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
O6 C8 C9 111.63(18) . . ?
O6 C8 C11 110.02(18) . . ?
O6 C8 C10 101.91(19) . . ?
C11 C8 C9 111.1(2) . . ?
C11 C8 C10 112.1(2) . . ?
C10 C8 C9 109.7(2) . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C3 C2 H2 118.5 . . ?
C1 C2 C3 123.0(3) . . ?
C1 C2 H2 118.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C2 C1 H1A 120.0 . . ?
C2 C1 H1B 120.0 . . ?
H1A C1 H1B 120.0 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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 C4 C5 C6 -171.31(14) . . . . ?
S1 C3 C2 C1 -116.8(3) . . . . ?
O4 C12 C6 N1 -179.63(17) . . . . ?
O4 C12 C6 C5 -54.1(2) . . . . ?
O3 C12 C6 N1 0.3(3) . . . . ?
O3 C12 C6 C5 125.8(2) . . . . ?
O2 S1 C4 C5 176.77(15) . . . . ?
O2 S1 C3 C2 -58.5(2) . . . . ?
O1 S1 C4 C5 -54.93(18) . . . . ?
O1 S1 C3 C2 173.05(18) . . . . ?
C7 O6 C8 C9 -55.0(3) . . . . ?
C7 O6 C8 C11 68.8(3) . . . . ?
C7 O6 C8 C10 -172.0(2) . . . . ?
C7 N1 C6 C12 -141.97(19) . . . . ?
C7 N1 C6 C5 92.4(2) . . . . ?
C12 O4 C13 C15 -61.1(2) . . . . ?
C12 O4 C13 C16 -178.92(18) . . . . ?
C12 O4 C13 C14 63.1(3) . . . . ?
C13 O4 C12 O3 -2.5(3) . . . . ?
C13 O4 C12 C6 177.45(17) . . . . ?
C4 S1 C3 C2 55.4(2) . . . . ?
C4 C5 C6 N1 65.5(2) . . . . ?
C4 C5 C6 C12 -59.1(2) . . . . ?
C6 N1 C7 O5 8.2(3) . . . . ?
C6 N1 C7 O6 -172.35(17) . . . . ?
C3 S1 C4 C5 62.08(18) . . . . ?
C8 O6 C7 O5 -0.9(3) . . . . ?
C8 O6 C7 N1 179.69(17) . . . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.205
_oxdiff_exptl_absorpt_empirical_full_min 0.857
####################################################################### 
# 
# 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_hpd150a
_database_code_depnum_ccdc_archive 'CCDC 2042732'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman'
;University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2020-11-05 deposited with the CCDC.	2022-03-21 downloaded from the CCDC.
;
_audit_creation_date             2020-07-07
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H22 O2 S'
_chemical_formula_sum            'C18 H22 O2 S'
_chemical_formula_weight         302.41
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H S O'
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'
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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   9.33740(10)
_cell_length_b                   6.06610(10)
_cell_length_c                   28.5106(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1614.89(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5874
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      76.3020
_cell_measurement_theta_min      3.0910
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.786
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.767
_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    1.244
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -3 4 0.0604
0 18 0 0.0469
0 -3 -4 0.0789
0 -18 0 0.0497
0 -9 3 0.0717
6 0 0 0.0268
-6 1 0 0.0207

_exptl_crystal_size_max          0.167
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.056
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
-0.6334 -3.3360 3.8548 0.0688 0.2790 0.9578
0.4631 18.4384 -0.1151 0.2034 0.8496 -0.4867
0.4795 -3.1150 -3.8709 -0.1415 -0.5826 -0.8003
-0.3739 -18.3197 -0.4870 -0.2186 -0.9120 0.3471
0.1311 -8.5478 3.4957 0.1350 -0.0343 0.9902
6.0260 0.4917 -0.3989 0.9489 -0.2278 -0.2182
-6.0564 0.5374 -0.0215 -0.9675 0.2324 0.0994

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            9898
_diffrn_reflns_point_group_measured_fraction_full 0.904
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.594
_diffrn_reflns_theta_min         3.100
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -75.00  26.00   0.50    0.05    --  -46.75  86.00 140.00  202
  2  ω   -162.00 -73.00   0.50    0.18    --  -88.50 -37.00 167.00  178
  3  ω    -43.00 -14.00   0.50    0.18    --  -88.50  37.00 -36.00   58
  4  ω     34.00 110.00   0.50    0.18    --  106.69-120.00 -54.00  152
  5  ω    101.00 178.00   0.50    0.18    --  106.69  86.00 140.00  154
  6  ω   -119.00 -83.00   0.50    0.05    --  -46.75 -57.00-150.00   72
  7  ω   -119.00 -54.00   0.50    0.05    --  -46.75-153.00 147.00  130
  8  ω     83.00 119.00   0.50    0.05    --   46.75  57.00-180.00   72
  9  ω    -51.00 -16.00   0.50    0.18    --  -88.50  45.00 150.00   70
 10  ω     34.00  71.00   0.50    0.18    --  106.69 -61.00-150.00   74
 11  ω     34.00  71.00   0.50    0.18    --  106.69 -61.00 -60.00   74
 12  ω     34.00 111.00   0.50    0.18    --  106.69-125.00  90.00  154
 13  ω     34.00  71.00   0.50    0.18    --  106.69 -61.00-180.00   74
 14  ω     34.00  71.00   0.50    0.18    --  106.69 -61.00 150.00   74
 15  ω     34.00  71.00   0.50    0.18    --  106.69 -61.00  60.00   74
 16  ω   -121.00 -32.00   0.50    0.05    --  -46.75 -37.00-120.00  178
 17  ω   -121.00 -32.00   0.50    0.05    --  -46.75 -37.00   0.00  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1602217000
_diffrn_orient_matrix_UB_12      0.0073219000
_diffrn_orient_matrix_UB_13      0.0505188000
_diffrn_orient_matrix_UB_21      -0.0345379000
_diffrn_orient_matrix_UB_22      0.0476175000
_diffrn_orient_matrix_UB_23      0.1079185000
_diffrn_orient_matrix_UB_31      -0.0193847000
_diffrn_orient_matrix_UB_32      -0.0245089000
_diffrn_orient_matrix_UB_33      0.2240752000
_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         0.711
_reflns_Friedel_fraction_full    0.805
_reflns_Friedel_fraction_max     0.719
_reflns_number_gt                2804
_reflns_number_total             2879
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 1127 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2879
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0313
_refine_ls_restrained_S_all      1.043
_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)+(0.0402P)²+0.4378P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0807
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C11(H11), C14(H14), C18(H18), C16(H16), C17(H17), C7(H7),
 C15(H15)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_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 0.27704(5) 0.33887(9) 0.53378(2) 0.01886(16) Uani 1 1 d . . . . .
O2 O 0.15339(18) 0.4736(3) 0.54508(6) 0.0237(4) Uani 1 1 d . . . . .
O1 O 0.2537(2) 0.1522(3) 0.50364(7) 0.0262(5) Uani 1 1 d . . . . .
C8 C 0.1010(3) -0.1905(4) 0.63383(10) 0.0226(6) Uani 1 1 d . . . . .
H8 H 0.068373 -0.329421 0.625085 0.027 Uiso 1 1 calc R U . . .
C1 C 0.3562(3) 0.2462(5) 0.58751(9) 0.0221(5) Uani 1 1 d . . . . .
H1A H 0.435429 0.148061 0.580537 0.027 Uiso 1 1 calc R U . . .
H1B H 0.393840 0.371845 0.604581 0.027 Uiso 1 1 calc R U . . .
C13 C 0.5190(3) 0.9345(5) 0.36055(9) 0.0232(6) Uani 1 1 d . . . . .
C10 C 0.0983(3) 0.1146(5) 0.68651(9) 0.0230(5) Uani 1 1 d . . . . .
H10 H 0.064138 0.182425 0.713541 0.028 Uiso 1 1 calc R U . . .
C9 C 0.0504(3) -0.0963(5) 0.67500(9) 0.0223(5) Uani 1 1 d . . . . .
C11 C 0.1960(3) 0.2250(5) 0.65833(10) 0.0218(5) Uani 1 1 d . . . . .
H11 H 0.226715 0.365415 0.666715 0.026 Uiso 1 1 calc R U . . .
C14 C 0.5859(3) 1.1380(5) 0.36527(10) 0.0271(6) Uani 1 1 d . . . . .
H14 H 0.557457 1.232934 0.389140 0.033 Uiso 1 1 calc R U . . .
C18 C 0.5633(3) 0.7983(5) 0.32421(10) 0.0254(6) Uani 1 1 d . . . . .
H18 H 0.519412 0.661904 0.320288 0.030 Uiso 1 1 calc R U . . .
C4 C 0.4690(3) 0.7374(5) 0.43695(9) 0.0224(5) Uani 1 1 d . . . . .
H4A H 0.538503 0.629787 0.426257 0.027 Uiso 1 1 calc R U . . .
H4B H 0.517931 0.841976 0.457086 0.027 Uiso 1 1 calc R U . . .
C2 C 0.4108(2) 0.5092(5) 0.50861(9) 0.0223(5) Uani 1 1 d . . . . .
H2A H 0.440640 0.619876 0.531138 0.027 Uiso 1 1 calc R U . . .
H2B H 0.493736 0.420838 0.500438 0.027 Uiso 1 1 calc R U . . .
C3 C 0.3516(3) 0.6218(5) 0.46459(10) 0.0222(5) Uani 1 1 d . . . . .
H3A H 0.306064 0.512282 0.444787 0.027 Uiso 1 1 calc R U . . .
H3B H 0.279484 0.728608 0.473664 0.027 Uiso 1 1 calc R U . . .
C16 C 0.7371(3) 1.0635(5) 0.29895(10) 0.0263(6) Uani 1 1 d . . . . .
H16 H 0.809449 1.106439 0.278481 0.032 Uiso 1 1 calc R U . . .
C17 C 0.6715(3) 0.8609(5) 0.29356(10) 0.0273(6) Uani 1 1 d . . . . .
H17 H 0.699744 0.766795 0.269515 0.033 Uiso 1 1 calc R U . . .
C7 C 0.1994(3) -0.0817(5) 0.60531(9) 0.0218(5) Uani 1 1 d . . . . .
H7 H 0.232304 -0.148726 0.578028 0.026 Uiso 1 1 calc R U . . .
C15 C 0.6949(3) 1.2020(5) 0.33480(11) 0.0292(6) Uani 1 1 d . . . . .
H15 H 0.739256 1.338121 0.338613 0.035 Uiso 1 1 calc R U . . .
C5 C 0.4057(3) 0.8583(5) 0.39477(10) 0.0272(6) Uani 1 1 d . . . . .
H5A H 0.339539 0.760978 0.378682 0.033 Uiso 1 1 calc R U . . .
H5B H 0.352106 0.985143 0.405736 0.033 Uiso 1 1 calc R U . . .
C12 C -0.0513(3) -0.2192(5) 0.70651(10) 0.0291(6) Uani 1 1 d . . . . .
H12A H -0.125853 -0.284597 0.687951 0.044 Uiso 1 1 calc R U . . .
H12B H -0.092784 -0.118668 0.728691 0.044 Uiso 1 1 calc R U . . .
H12C H -0.000258 -0.332635 0.722979 0.044 Uiso 1 1 calc R U . . .
C6 C 0.2485(3) 0.1273(5) 0.61762(10) 0.0204(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4507(18) . ?
S1 O1 1.438(2) . ?
S1 C1 1.791(3) . ?
S1 C2 1.773(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.388(4) . ?
C8 C7 1.393(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C6 1.506(4) . ?
C13 C14 1.390(4) . ?
C13 C18 1.388(4) . ?
C13 C5 1.511(4) . ?
C10 H10 0.9300 . ?
C10 C9 1.394(4) . ?
C10 C11 1.388(4) . ?
C9 C12 1.505(4) . ?
C11 H11 0.9300 . ?
C11 C6 1.392(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.393(4) . ?
C18 H18 0.9300 . ?
C18 C17 1.389(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C3 1.521(3) . ?
C4 C5 1.527(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.532(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C16 H16 0.9300 . ?
C16 C17 1.382(4) . ?
C16 C15 1.381(4) . ?
C17 H17 0.9300 . ?
C7 H7 0.9300 . ?
C7 C6 1.394(4) . ?
C15 H15 0.9300 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 C1 108.38(12) . . ?
O2 S1 C2 108.81(12) . . ?
O1 S1 O2 117.09(11) . . ?
O1 S1 C1 109.06(13) . . ?
O1 S1 C2 108.90(13) . . ?
C2 S1 C1 103.78(12) . . ?
C9 C8 H8 119.2 . . ?
C9 C8 C7 121.5(3) . . ?
C7 C8 H8 119.2 . . ?
S1 C1 H1A 109.4 . . ?
S1 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
C6 C1 S1 111.22(17) . . ?
C6 C1 H1A 109.4 . . ?
C6 C1 H1B 109.4 . . ?
C14 C13 C5 121.6(3) . . ?
C18 C13 C14 117.8(2) . . ?
C18 C13 C5 120.6(3) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C11 C10 C9 121.1(3) . . ?
C8 C9 C10 117.9(2) . . ?
C8 C9 C12 121.0(3) . . ?
C10 C9 C12 121.1(3) . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C6 120.6(3) . . ?
C6 C11 H11 119.7 . . ?
C13 C14 H14 119.5 . . ?
C13 C14 C15 121.0(3) . . ?
C15 C14 H14 119.5 . . ?
C13 C18 H18 119.2 . . ?
C13 C18 C17 121.6(3) . . ?
C17 C18 H18 119.2 . . ?
H4A C4 H4B 108.1 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 C5 110.6(2) . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
S1 C2 H2A 109.7 . . ?
S1 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C3 C2 S1 109.70(16) . . ?
C3 C2 H2A 109.7 . . ?
C3 C2 H2B 109.7 . . ?
C4 C3 C2 111.7(2) . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.8(3) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 C18 119.7(3) . . ?
C16 C17 H17 120.2 . . ?
C8 C7 H7 120.0 . . ?
C8 C7 C6 120.1(3) . . ?
C6 C7 H7 120.0 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 H15 120.0 . . ?
C13 C5 C4 112.6(2) . . ?
C13 C5 H5A 109.1 . . ?
C13 C5 H5B 109.1 . . ?
C4 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C6 C1 120.4(3) . . ?
C11 C6 C7 118.8(2) . . ?
C7 C6 C1 120.8(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C1 C6 C11 -108.2(3) . . . . ?
S1 C1 C6 C7 71.7(3) . . . . ?
S1 C2 C3 C4 -170.0(2) . . . . ?
O2 S1 C1 C6 55.4(2) . . . . ?
O2 S1 C2 C3 -58.5(2) . . . . ?
O1 S1 C1 C6 -73.1(2) . . . . ?
O1 S1 C2 C3 70.1(2) . . . . ?
C8 C7 C6 C1 179.3(2) . . . . ?
C8 C7 C6 C11 -0.8(4) . . . . ?
C1 S1 C2 C3 -173.79(19) . . . . ?
C13 C14 C15 C16 0.6(4) . . . . ?
C13 C18 C17 C16 -0.2(4) . . . . ?
C10 C11 C6 C1 -179.1(2) . . . . ?
C10 C11 C6 C7 1.0(4) . . . . ?
C9 C8 C7 C6 -0.6(4) . . . . ?
C9 C10 C11 C6 0.2(4) . . . . ?
C11 C10 C9 C8 -1.5(4) . . . . ?
C11 C10 C9 C12 177.7(3) . . . . ?
C14 C13 C18 C17 0.5(4) . . . . ?
C14 C13 C5 C4 -88.2(3) . . . . ?
C18 C13 C14 C15 -0.7(4) . . . . ?
C18 C13 C5 C4 89.4(3) . . . . ?
C2 S1 C1 C6 170.9(2) . . . . ?
C3 C4 C5 C13 -167.7(2) . . . . ?
C17 C16 C15 C14 -0.4(4) . . . . ?
C7 C8 C9 C10 1.7(4) . . . . ?
C7 C8 C9 C12 -177.5(2) . . . . ?
C15 C16 C17 C18 0.2(4) . . . . ?
C5 C13 C14 C15 176.9(3) . . . . ?
C5 C13 C18 C17 -177.2(3) . . . . ?
C5 C4 C3 C2 -177.0(2) . . . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.250
_oxdiff_exptl_absorpt_empirical_full_min 0.826
####################################################################### 
# 
# 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_hpd124
_database_code_depnum_ccdc_archive 'CCDC 2042726'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman'
;University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2020-11-05 deposited with the CCDC.	2022-03-21 downloaded from the CCDC.
;
_audit_creation_date             2020-06-17
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H20 Cl N O3 S'
_chemical_formula_sum            'C15 H20 Cl N O3 S'
_chemical_formula_weight         329.83
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Cl'
_chemical_oxdiff_usercomment     VNY138-13
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'
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                   5.01880(10)
_cell_length_b                   9.6241(2)
_cell_length_c                   16.1198(4)
_cell_angle_alpha                89.487(2)
_cell_angle_beta                 85.132(2)
_cell_angle_gamma                82.136(2)
_cell_volume                     768.50(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7974
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.2340
_cell_measurement_theta_min      2.7280
_shelx_estimated_absorpt_T_max   0.812
_shelx_estimated_absorpt_T_min   0.538
_exptl_absorpt_coefficient_mu    3.554
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.601
_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    1.425
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             348
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -6 4 0.0854
3 2 -2 0.0640
0 6 -4 0.0882
-3 -3 3 0.0476
3 -2 0 0.0972
0 -3 -9 0.0331
-3 2 1 0.0510
0 3 10 0.0227

_exptl_crystal_size_max          0.199
_exptl_crystal_size_mid          0.13
_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
0.3743 -5.6990 3.5739 -0.2030 -0.8479 0.4897
3.0406 1.8582 -2.4648 0.1465 0.6034 0.7838
0.0489 5.7779 -3.7993 0.2167 0.9039 -0.3687
-2.9100 -2.5229 2.8459 -0.1680 -0.6933 -0.7008
2.9120 -1.9699 0.0095 0.0082 -0.0038 1.0000
0.0457 -2.8130 -9.2497 0.9351 -0.2253 0.2736
-2.7620 2.2934 1.4039 -0.1506 0.0381 -0.9879
0.3191 2.6446 9.5115 -0.9604 0.2312 -0.1556

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14635
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.472
_diffrn_reflns_theta_min         2.751
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     34.00  95.00   0.50    0.05    --   46.62-125.00 152.00  122
  2  ω     34.00 111.00   0.50    0.05    --  106.69-125.00 152.00  154
  3  ω     34.00 101.00   0.50    0.05    --  106.69 -77.00   0.00  134
  4  ω     45.00 126.00   0.50    0.05    --  106.69-145.00 -15.00  162
  5  ω     45.00 107.00   0.50    0.05    --   46.62-145.00 -15.00  124
  6  ω     34.00 111.00   0.50    0.05    --  106.69-125.00-120.00  154
  7  ω     34.00 101.00   0.50    0.05    --  106.69 -77.00-150.00  134
  8  ω     34.00 105.00   0.50    0.05    --  106.69 -94.00 -30.00  142
  9  ω     34.00 105.00   0.50    0.05    --  106.69 -94.00   0.00  142
 10  ω     34.00  71.00   0.50    0.05    --  106.69 -61.00 150.00   74
 11  ω     34.00 101.00   0.50    0.05    --  106.69 -77.00 150.00  134
 12  ω     34.00  71.00   0.50    0.05    --  106.69 -61.00  30.00   74
 13  ω    101.00 178.00   0.50    0.05    --  106.69  77.00-150.00  154
 14  ω     95.00 178.00   0.50    0.05    --  106.69 125.00-129.00  166
 15  ω     91.00 178.00   0.50    0.05    --  106.69  30.00-180.00  174
 16  ω     81.00 170.00   0.50    0.05    --  106.69 145.00  37.00  178
 17  ω    101.00 178.00   0.50    0.05    --  106.69  77.00  90.00  154
 18  ω    -51.00 -16.00   0.50    0.05    --  -88.50  45.00   0.00   70
 19  ω    -51.00 -16.00   0.50    0.05    --  -88.50  45.00  30.00   70
 20  ω    -71.00 -15.00   0.50    0.05    --  -88.50  61.00  90.00  112
 21  ω   -101.00 -23.00   0.50    0.05    --  -46.62 145.00  37.00  156
 22  ω    -86.00 -15.00   0.50    0.05    --  -88.50 125.00-129.00  142
 23  ω    -51.00 -16.00   0.50    0.05    --  -88.50  45.00-180.00   70
 24  ω    -86.00 -13.00   0.50    0.05    --  -46.62 125.00-129.00  146
 25  ω   -120.00 -32.00   0.50    0.05    --  -46.62 -37.00 -60.00  176
 26  ω   -119.00 -60.00   0.50    0.05    --  -46.62-145.00 -15.00  118
 27  ω   -119.00 -83.00   0.50    0.05    --  -46.62 -57.00 120.00   72
 28  ω   -119.00 -83.00   0.50    0.05    --  -46.62 -57.00 150.00   72
 29  ω   -120.00 -32.00   0.50    0.05    --  -46.62 -37.00 120.00  176
 30  ω   -119.00 -73.00   0.50    0.05    --  -46.62-125.00 152.00   92
 31  ω   -119.00 -83.00   0.50    0.05    --  -46.62 -57.00-120.00   72
 32  ω   -119.00 -83.00   0.50    0.05    --  -46.62 -57.00-180.00   72
 33  ω   -120.00 -32.00   0.50    0.05    --  -46.62 -37.00-150.00  176
 34  ω   -119.00 -83.00   0.50    0.05    --  -46.62 -57.00 -90.00   72
 35  ω   -120.00 -32.00   0.50    0.05    --  -46.62 -37.00 -90.00  176
 36  ω   -120.00 -32.00   0.50    0.05    --  -46.62 -37.00  30.00  176
 37  ω   -120.00 -52.00   0.50    0.05    --  -46.62 -37.00  60.00  136
 38  ω   -119.00 -83.00   0.50    0.05    --  -46.62 -57.00  60.00   72
 39  ω   -152.00 -60.00   0.50    0.05    --  -88.50-145.00 -15.00  184
 40  ω   -160.00 -91.00   0.50    0.05    --  -88.50 -61.00  30.00  138
 41  ω   -160.00-100.00   0.50    0.05    --  -88.50 -94.00   0.00  120
 42  ω   -163.00 -73.00   0.50    0.05    --  -88.50 -30.00-150.00  180
 43  ω   -160.00-101.00   0.50    0.05    --  -88.50 -77.00-180.00  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      -0.0131563000
_diffrn_orient_matrix_UB_12      -0.0240891000
_diffrn_orient_matrix_UB_13      -0.0938319000
_diffrn_orient_matrix_UB_21      0.0956847000
_diffrn_orient_matrix_UB_22      0.1433082000
_diffrn_orient_matrix_UB_23      -0.0187491000
_diffrn_orient_matrix_UB_31      0.2956050000
_diffrn_orient_matrix_UB_32      -0.0706753000
_diffrn_orient_matrix_UB_33      -0.0066266000
_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                2859
_reflns_number_total             3083
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT n/a (Sheldrick, 2015)'
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.059
_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     199
_refine_ls_number_reflns         3083
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0347
_refine_ls_restrained_S_all      1.062
_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)+(0.0400P)²+0.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0883
_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 Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C8(H8A,H8B), C13(H13A,H13B), C9(H9A,H9B), C11(H11A,H11B),
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C3(H3), C14(H14), C2(H2)
;
_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 1.29108(8) 0.08561(4) 0.70567(2) 0.01878(12) Uani 1 1 d . . . . .
Cl1 Cl -0.35633(8) 0.30700(4) 0.02985(2) 0.02364(12) Uani 1 1 d . . . . .
O3 O 1.4890(2) -0.02547(12) 0.66924(8) 0.0258(3) Uani 1 1 d . . . . .
O1 O 0.3682(2) 0.56813(12) 0.30473(8) 0.0239(3) Uani 1 1 d . . . . .
O2 O 1.0367(2) 0.04602(13) 0.73893(8) 0.0277(3) Uani 1 1 d . . . . .
N1 N 0.5094(3) 0.34107(15) 0.32986(9) 0.0198(3) Uani 1 1 d . . . . .
C7 C 0.3664(3) 0.44256(17) 0.28850(10) 0.0187(3) Uani 1 1 d . . . . .
C6 C -0.0404(3) 0.23780(17) 0.15535(11) 0.0206(3) Uani 1 1 d . . . . .
H6 H -0.086307 0.145917 0.150114 0.025 Uiso 1 1 calc R U . . .
C5 C 0.1288(3) 0.26675(17) 0.21512(10) 0.0194(3) Uani 1 1 d . . . . .
H5 H 0.198755 0.194293 0.250897 0.023 Uiso 1 1 calc R U . . .
C3 C 0.0941(3) 0.50623(18) 0.16925(11) 0.0212(3) Uani 1 1 d . . . . .
H3 H 0.141379 0.597985 0.173692 0.025 Uiso 1 1 calc R U . . .
C12 C 1.2239(3) 0.21944(17) 0.63106(11) 0.0204(3) Uani 1 1 d . . . . .
H12A H 1.106676 0.300356 0.658129 0.025 Uiso 1 1 calc R U . . .
H12B H 1.395502 0.251664 0.609394 0.025 Uiso 1 1 calc R U . . .
C4 C 0.1962(3) 0.40190(17) 0.22276(10) 0.0182(3) Uani 1 1 d . . . . .
C14 C 1.4477(4) 0.08091(18) 0.86217(11) 0.0240(4) Uani 1 1 d . . . . .
H14 H 1.596680 0.008935 0.864479 0.029 Uiso 1 1 calc R U . . .
C8 C 0.6796(3) 0.37711(17) 0.39318(10) 0.0197(3) Uani 1 1 d . . . . .
H8A H 0.568946 0.440519 0.434696 0.024 Uiso 1 1 calc R U . . .
H8B H 0.822677 0.428129 0.366681 0.024 Uiso 1 1 calc R U . . .
C13 C 1.4331(3) 0.17088(17) 0.78603(11) 0.0214(3) Uani 1 1 d . . . . .
H13A H 1.616562 0.189972 0.766034 0.026 Uiso 1 1 calc R U . . .
H13B H 1.320722 0.261715 0.799997 0.026 Uiso 1 1 calc R U . . .
C9 C 0.8096(3) 0.24854(17) 0.43729(10) 0.0204(3) Uani 1 1 d . . . . .
H9A H 0.928199 0.187132 0.396514 0.025 Uiso 1 1 calc R U . . .
H9B H 0.667620 0.194944 0.461931 0.025 Uiso 1 1 calc R U . . .
C1 C -0.1411(3) 0.34405(18) 0.10366(10) 0.0194(3) Uani 1 1 d . . . . .
C2 C -0.0752(3) 0.47903(18) 0.10957(11) 0.0221(4) Uani 1 1 d . . . . .
H2 H -0.144780 0.551108 0.073475 0.027 Uiso 1 1 calc R U . . .
C11 C 1.0857(3) 0.16747(17) 0.55886(11) 0.0211(3) Uani 1 1 d . . . . .
H11A H 0.936069 0.116722 0.580855 0.025 Uiso 1 1 calc R U . . .
H11B H 1.216703 0.101459 0.524062 0.025 Uiso 1 1 calc R U . . .
C10 C 0.9753(3) 0.29103(17) 0.50584(10) 0.0203(3) Uani 1 1 d . . . . .
H10A H 1.128155 0.335766 0.480026 0.024 Uiso 1 1 calc R U . . .
H10B H 0.860729 0.361449 0.542398 0.024 Uiso 1 1 calc R U . . .
C15 C 1.2654(4) 0.0964(2) 0.92580(12) 0.0291(4) Uani 1 1 d . . . . .
H15A H 1.277(4) 0.038(2) 0.9764(15) 0.035 Uiso 1 1 d . U . . .
H1 H 0.516(5) 0.257(3) 0.3167(14) 0.035 Uiso 1 1 d . U . . .
H15B H 1.112(5) 0.165(2) 0.9259(14) 0.035 Uiso 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.4476(13) . ?
S1 O2 1.4407(13) . ?
S1 C12 1.7723(17) . ?
S1 C13 1.7877(17) . ?
Cl1 C1 1.7438(16) . ?
O1 C7 1.240(2) . ?
N1 C7 1.338(2) . ?
N1 C8 1.458(2) . ?
C7 C4 1.503(2) . ?
C6 C5 1.391(2) . ?
C6 C1 1.382(2) . ?
C5 C4 1.397(2) . ?
C3 C4 1.391(2) . ?
C3 C2 1.386(2) . ?
C12 C11 1.526(2) . ?
C14 C13 1.497(2) . ?
C14 C15 1.311(3) . ?
C8 C9 1.518(2) . ?
C9 C10 1.529(2) . ?
C1 C2 1.390(2) . ?
C11 C10 1.528(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 C12 109.61(8) . . ?
O3 S1 C13 109.55(8) . . ?
O2 S1 O3 116.63(8) . . ?
O2 S1 C12 107.96(8) . . ?
O2 S1 C13 108.49(8) . . ?
C12 S1 C13 103.83(8) . . ?
C7 N1 C8 120.08(14) . . ?
O1 C7 N1 121.24(15) . . ?
O1 C7 C4 119.99(14) . . ?
N1 C7 C4 118.76(14) . . ?
C1 C6 C5 119.34(15) . . ?
C6 C5 C4 120.30(15) . . ?
C2 C3 C4 121.31(16) . . ?
C11 C12 S1 111.39(11) . . ?
C5 C4 C7 123.24(15) . . ?
C3 C4 C7 117.69(14) . . ?
C3 C4 C5 119.03(15) . . ?
C15 C14 C13 123.31(17) . . ?
N1 C8 C9 112.27(13) . . ?
C14 C13 S1 110.49(12) . . ?
C8 C9 C10 110.68(13) . . ?
C6 C1 Cl1 118.91(13) . . ?
C6 C1 C2 121.46(15) . . ?
C2 C1 Cl1 119.63(13) . . ?
C3 C2 C1 118.56(15) . . ?
C12 C11 C10 110.22(13) . . ?
C11 C10 C9 113.15(13) . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.443
_oxdiff_exptl_absorpt_empirical_full_min 0.743
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_hpd132
_database_code_depnum_ccdc_archive 'CCDC 2042729'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman'
;University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2020-11-05 deposited with the CCDC.	2022-03-21 downloaded from the CCDC.
;
_audit_creation_date             2020-06-24
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H18 O4 S2'
_chemical_formula_sum            'C10 H18 O4 S2'
_chemical_formula_weight         266.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H S O'
_chemical_oxdiff_usercomment     'Alkene sulfone'
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'
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                   6.46910(10)
_cell_length_b                   11.4368(2)
_cell_length_c                   8.73870(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.114(2)
_cell_angle_gamma                90
_cell_volume                     632.142(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4860
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.2320
_cell_measurement_theta_min      6.4440
_shelx_estimated_absorpt_T_max   0.681
_shelx_estimated_absorpt_T_min   0.483
_exptl_absorpt_coefficient_mu    3.818
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.732
_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    1.399
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             284
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 1 -5 0.0806
-1 -7 -1 0.0638
-3 -3 4 0.0919
0 7 2 0.0479
4 0 1 0.0176
0 -4 5 0.0238
-4 -1 0 0.0950
-1 4 -4 0.0835

_exptl_crystal_size_max          0.223
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.109
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2.9833 1.2791 -4.6315 0.0903 0.3688 0.9251
-0.7568 -7.1806 -0.7673 0.1966 0.8217 -0.5349
-2.9219 -3.3040 3.9551 -0.0228 -0.0874 -0.9959
0.1762 7.0363 1.6983 -0.2175 -0.9074 0.3595
4.0036 0.4319 0.5104 0.8288 -0.2003 0.5224
0.0397 -4.0792 4.6214 0.6817 -0.1626 -0.7134
-4.0574 -0.7437 -0.1713 -0.7895 0.1909 -0.5833
-0.8180 3.7417 -4.4341 -0.8010 0.1915 0.5672

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6099
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.450
_diffrn_reflns_theta_min         6.467
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  72.00   0.50    0.05    --   46.87 -79.00  -2.00  194
  2  ω     34.00 109.00   0.50    0.05    --  106.69 -79.00  -2.00  150
  3  ω     34.00  71.00   0.50    0.05    --  106.69 -61.00  30.00   74
  4  ω     34.00  71.00   0.50    0.05    --  106.69 -61.00  60.00   74
  5  ω     34.00 101.00   0.50    0.05    --  106.69 -77.00  30.00  134
  6  ω     34.00  71.00   0.50    0.05    --  106.69 -61.00 -90.00   74
  7  ω     34.00 105.00   0.50    0.05    --  106.69 -94.00-150.00  142
  8  ω     34.00 105.00   0.50    0.05    --  106.69 -94.00-120.00  142
  9  ω     32.00 121.00   0.50    0.05    --   46.87  37.00 -90.00  178
 10  ω     83.00 120.00   0.50    0.05    --   46.87  57.00  30.00   74
 11  ω     82.00 178.00   0.50    0.05    --  106.69  79.00 121.00  192
 12  ω     34.00  71.00   0.50    0.05    --  106.69 -61.00 150.00   74
 13  ω     32.00  89.00   0.50    0.05    --   46.87  37.00  30.00  114
 14  ω     22.00 120.00   0.50    0.05    --   46.87  79.00 121.00  196
 15  ω    -51.00 -16.00   0.50    0.05    --  -88.50  45.00-180.00   70
 16  ω    -51.00 -16.00   0.50    0.05    --  -88.50  45.00 -30.00   70
 17  ω    -71.00  26.00   0.50    0.05    --  -46.87  79.00 121.00  194
 18  ω   -109.00 -15.00   0.50    0.05    --  -88.50  79.00 121.00  188
 19  ω   -120.00 -22.00   0.50    0.05    --  -46.87 -79.00  -2.00  196
 20  ω   -120.00 -87.00   0.50    0.05    --  -46.87-125.00 150.00   66
 21  ω   -160.00-101.00   0.50    0.05    --  -88.50 -77.00 120.00  118
 22  ω   -160.00-101.00   0.50    0.05    --  -88.50 -77.00-120.00  118
 23  ω   -120.00 -87.00   0.50    0.05    --  -46.87-125.00-180.00   66
;
_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      0.2013653000
_diffrn_orient_matrix_UB_12      -0.0586475000
_diffrn_orient_matrix_UB_13      0.0940030000
_diffrn_orient_matrix_UB_21      -0.0237690000
_diffrn_orient_matrix_UB_22      -0.0988662000
_diffrn_orient_matrix_UB_23      -0.1222397000
_diffrn_orient_matrix_UB_31      0.1348227000
_diffrn_orient_matrix_UB_32      0.0702779000
_diffrn_orient_matrix_UB_33      -0.0934918000
_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                1234
_reflns_number_total             1265
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT n/a (Sheldrick, 2015)'
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.0044(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   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     74
_refine_ls_number_reflns         1265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0290
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0387P)²+0.4333P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0774
_refine_ls_wR_factor_ref         0.0777
_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 Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2)
2.c X=CH2 refined with riding coordinates:
 C1(H1A,H1B)
;
_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 0.59637(5) 0.69609(3) 0.40237(4) 0.01482(16) Uani 1 1 d . . . . .
O2 O 0.69800(17) 0.76582(10) 0.30109(12) 0.0206(3) Uani 1 1 d . . . . .
O1 O 0.42568(17) 0.62057(10) 0.32642(13) 0.0220(3) Uani 1 1 d . . . . .
C4 C 0.7890(2) 0.61133(13) 0.52940(17) 0.0175(3) Uani 1 1 d . . . . .
H4A H 0.885964 0.664283 0.600178 0.021 Uiso 1 1 calc R U . . .
H4B H 0.717571 0.561083 0.594711 0.021 Uiso 1 1 calc R U . . .
C5 C 0.9175(2) 0.53452(13) 0.44125(17) 0.0186(3) Uani 1 1 d . . . . .
H5A H 0.989301 0.583897 0.375204 0.022 Uiso 1 1 calc R U . . .
H5B H 0.822447 0.479718 0.372125 0.022 Uiso 1 1 calc R U . . .
C3 C 0.5016(3) 0.79264(13) 0.53294(17) 0.0184(3) Uani 1 1 d . . . . .
H3A H 0.426194 0.747424 0.600937 0.022 Uiso 1 1 calc R U . . .
H3B H 0.622112 0.833352 0.600517 0.022 Uiso 1 1 calc R U . . .
C2 C 0.3547(2) 0.88041(13) 0.43998(17) 0.0191(3) Uani 1 1 d . . . . .
H2 H 0.411318 0.934308 0.376952 0.023 Uiso 1 1 calc R U . . .
C1 C 0.1523(3) 0.88713(15) 0.4406(2) 0.0254(4) Uani 1 1 d . . . . .
H1A H 0.091172 0.834397 0.502477 0.030 Uiso 1 1 calc R U . . .
H1B H 0.067008 0.944720 0.379134 0.030 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4476(11) . ?
S1 O1 1.4486(11) . ?
S1 C4 1.7731(15) . ?
S1 C3 1.7863(15) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.525(2) . ?
C5 C5 1.535(3) 3_766 ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C2 1.499(2) . ?
C2 H2 0.9500 . ?
C2 C1 1.312(2) . ?
C1 H1A 0.9500 . ?
C1 H1B 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
O2 S1 O1 116.66(7) . . ?
O2 S1 C4 109.53(7) . . ?
O2 S1 C3 108.11(7) . . ?
O1 S1 C4 109.20(7) . . ?
O1 S1 C3 109.30(7) . . ?
C4 S1 C3 103.20(7) . . ?
S1 C4 H4A 109.1 . . ?
S1 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 S1 112.63(10) . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C4 C5 C5 109.55(15) . 3_766 ?
C4 C5 H5A 109.8 . . ?
C4 C5 H5B 109.8 . . ?
C5 C5 H5A 109.8 3_766 . ?
C5 C5 H5B 109.8 3_766 . ?
H5A C5 H5B 108.2 . . ?
S1 C3 H3A 109.8 . . ?
S1 C3 H3B 109.8 . . ?
H3A C3 H3B 108.3 . . ?
C2 C3 S1 109.36(10) . . ?
C2 C3 H3A 109.8 . . ?
C2 C3 H3B 109.8 . . ?
C3 C2 H2 118.1 . . ?
C1 C2 C3 123.82(15) . . ?
C1 C2 H2 118.1 . . ?
C2 C1 H1A 120.0 . . ?
C2 C1 H1B 120.0 . . ?
H1A C1 H1B 120.0 . . ?

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 C4 C5 C5 179.16(13) . . . 3_766 ?
S1 C3 C2 C1 114.95(16) . . . . ?
O2 S1 C4 C5 -56.05(13) . . . . ?
O2 S1 C3 C2 57.22(12) . . . . ?
O1 S1 C4 C5 72.82(12) . . . . ?
O1 S1 C3 C2 -70.70(12) . . . . ?
C4 S1 C3 C2 173.19(11) . . . . ?
C3 S1 C4 C5 -171.00(11) . . . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.470
_oxdiff_exptl_absorpt_empirical_full_min 0.712
####################################################################### 
# 
# 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_hpd133
_database_code_depnum_ccdc_archive 'CCDC 2042733'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman'
;University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2020-11-05 deposited with the CCDC.	2022-03-21 downloaded from the CCDC.
;
_audit_creation_date             2020-06-24
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H14 O3 S'
_chemical_formula_sum            'C11 H14 O3 S'
_chemical_formula_weight         226.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O S'
_chemical_oxdiff_usercomment     'VNY 130-1'
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'
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                   5.72076(11)
_cell_length_b                   8.13039(16)
_cell_length_c                   11.8424(2)
_cell_angle_alpha                91.8184(16)
_cell_angle_beta                 91.4466(15)
_cell_angle_gamma                103.4125(17)
_cell_volume                     535.218(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7153
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.0380
_cell_measurement_theta_min      3.7250
_shelx_estimated_absorpt_T_max   0.726
_shelx_estimated_absorpt_T_min   0.652
_exptl_absorpt_coefficient_mu    2.571
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.354
_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    1.404
_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
-1 2 -7 0.0629
-2 -3 -1 0.0828
1 -2 7 0.1000
2 3 0 0.0502
0 3 -6 0.0637
3 -4 -3 0.0638
0 -2 7 0.0968
-3 3 4 0.0582

_exptl_crystal_size_max          0.182
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.133
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
-1.0539 2.0126 -6.9703 0.0939 0.3836 0.9187
-2.3157 -3.1625 -0.8971 0.2206 0.9197 -0.3247
0.9772 -2.1242 6.9536 -0.0866 -0.3531 -0.9316
2.1676 3.4499 -0.0909 -0.2074 -0.8659 0.4552
0.1044 2.9235 -6.4489 0.0653 -0.0176 0.9977
2.7606 -3.8563 -2.6111 0.9678 -0.2325 -0.0968
-0.4234 -2.4676 6.7296 -0.1771 0.0444 -0.9832
-2.7477 3.2751 3.7643 -0.9685 0.2330 -0.0874

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9842
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.351
_diffrn_reflns_theta_min         3.736
_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 0.997
_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    -57.00  26.00   0.50    0.05    --  -46.87  50.00 -73.00  166
  2  ω    -57.00 -15.00   0.50    0.05    --  -88.50  50.00 -73.00   84
  3  ω    -51.00 -16.00   0.50    0.05    --  -88.50  45.00-150.00   70
  4  ω    -51.00 -16.00   0.50    0.05    --  -88.50  45.00-120.00   70
  5  ω    -71.00 -15.00   0.50    0.05    --  -88.50  61.00 -30.00  112
  6  ω    -86.00 -15.00   0.50    0.05    --  -88.50 125.00  30.00  142
  7  ω   -119.00 -33.00   0.50    0.05    --  -46.87 -44.00-163.96  172
  8  ω     32.00 120.00   0.50    0.05    --   46.87  50.00 -73.00  176
  9  ω     92.00 178.00   0.50    0.05    --  106.69  50.00 -73.00  172
 10  ω     34.00 101.00   0.50    0.05    --  106.69 -77.00 120.00  134
 11  ω     34.00 105.00   0.50    0.05    --  106.69 -94.00 150.00  142
 12  ω     34.00 101.00   0.50    0.05    --  106.69 -77.00  30.00  134
 13  ω     34.00 178.00   0.50    0.05    --  106.69   0.00  90.00  288
 14  ω     34.00  71.00   0.50    0.05    --  106.69 -61.00  30.00   74
 15  ω     34.00 106.00   0.50    0.05    --  106.69-100.00  29.22  144
 16  ω     34.00 111.00   0.50    0.05    --  106.69-125.00 150.00  154
 17  ω     34.00 111.00   0.50    0.05    --  106.69-125.00  30.00  154
 18  ω     34.00  71.00   0.50    0.05    --  106.69 -61.00 150.00   74
 19  ω     32.00 120.00   0.50    0.05    --   46.87  51.00  95.14  176
 20  ω     34.00  71.00   0.50    0.05    --  106.69 -61.00 -60.00   74
 21  ω     34.00 105.00   0.50    0.05    --  106.69 -94.00 -90.00  142
 22  ω     34.00 108.00   0.50    0.05    --  106.69-107.00-124.10  148
 23  ω     32.00 120.00   0.50    0.05    --   46.87  49.00 -30.13  176
 24  ω     32.00 120.00   0.50    0.05    --   46.87  54.00 133.94  176
 25  ω     32.00 120.00   0.50    0.05    --   46.87  53.00  23.01  176
 26  ω     32.00 120.00   0.50    0.05    --   46.87  53.00-177.98  176
 27  ω    -28.00  30.00   0.50    0.05    --   46.87 -19.00   0.00  116
 28  ω    -25.00  57.00   0.50    0.05    --   46.87 -50.00 139.00  164
 29  ω    -28.00  30.00   0.50    0.05    --   46.87 -19.00 150.00  116
 30  ω    -28.00  30.00   0.50    0.05    --   46.87 -19.00  30.00  116
 31  ω   -120.00 -32.00   0.50    0.05    --  -46.87 -50.00 139.00  176
 32  ω   -160.00 -73.00   0.50    0.05    --  -88.50 -50.00 139.00  174
 33  ω   -160.00 -91.00   0.50    0.05    --  -88.50 -61.00  90.00  138
 34  ω   -160.00 -73.00   0.50    0.05    --  -88.50 -55.00 -15.55  174
 35  ω   -160.00-101.00   0.50    0.05    --  -88.50 -77.00-150.00  118
 36  ω   -160.00 -87.00   0.50    0.05    --  -88.50-125.00 -90.00  146
 37  ω   -160.00 -72.00   0.50    0.05    --  -88.50 -54.00-130.79  176
;
_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      0.1069627000
_diffrn_orient_matrix_UB_12      -0.1290777000
_diffrn_orient_matrix_UB_13      -0.0669140000
_diffrn_orient_matrix_UB_21      -0.2542305000
_diffrn_orient_matrix_UB_22      -0.0923971000
_diffrn_orient_matrix_UB_23      -0.0432786000
_diffrn_orient_matrix_UB_31      0.0255891000
_diffrn_orient_matrix_UB_32      0.1131529000
_diffrn_orient_matrix_UB_33      -0.1029988000
_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                2088
_reflns_number_total             2143
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT n/a (Sheldrick, 2015)'
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0041(8)
_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   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2143
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0287
_refine_ls_restrained_S_all      1.038
_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)+(0.0416P)²+0.2889P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0780
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C2(H2), C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_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 0.95023(5) 0.73697(4) 0.91640(2) 0.01300(12) Uani 1 1 d . . . . .
O2 O 0.95260(17) 0.89115(12) 0.85831(8) 0.0183(2) Uani 1 1 d . . . . .
O3 O 1.17817(17) 0.71165(13) 0.95957(8) 0.0198(2) Uani 1 1 d . . . . .
O1 O 0.22259(17) 0.59826(13) 0.61273(8) 0.0201(2) Uani 1 1 d . . . . .
C8 C 0.6449(2) 0.67239(16) 0.65341(11) 0.0139(3) Uani 1 1 d . . . . .
H8A H 0.726036 0.790985 0.674783 0.017 Uiso 1 1 calc R U . . .
H8B H 0.756828 0.623759 0.607745 0.017 Uiso 1 1 calc R U . . .
C1 C 0.4483(2) 0.75969(16) 0.47278(11) 0.0136(3) Uani 1 1 d . . . . .
C7 C 0.4215(2) 0.67083(16) 0.58226(11) 0.0137(3) Uani 1 1 d . . . . .
C9 C 0.5911(2) 0.57265(17) 0.76052(11) 0.0142(3) Uani 1 1 d . . . . .
H9A H 0.494999 0.457413 0.739807 0.017 Uiso 1 1 calc R U . . .
H9B H 0.493560 0.628538 0.810098 0.017 Uiso 1 1 calc R U . . .
C10 C 0.8201(2) 0.55925(16) 0.82585(11) 0.0145(3) Uani 1 1 d . . . . .
H10A H 0.940873 0.542749 0.770808 0.017 Uiso 1 1 calc R U . . .
H10B H 0.782308 0.457427 0.871829 0.017 Uiso 1 1 calc R U . . .
C6 C 0.6698(2) 0.85573(17) 0.43997(11) 0.0157(3) Uani 1 1 d . . . . .
H6 H 0.809387 0.864190 0.487043 0.019 Uiso 1 1 calc R U . . .
C5 C 0.6869(3) 0.93899(18) 0.33866(12) 0.0190(3) Uani 1 1 d . . . . .
H5 H 0.837861 1.004443 0.316907 0.023 Uiso 1 1 calc R U . . .
C2 C 0.2445(2) 0.74728(17) 0.40237(11) 0.0161(3) Uani 1 1 d . . . . .
H2 H 0.093330 0.681676 0.423761 0.019 Uiso 1 1 calc R U . . .
C3 C 0.2626(3) 0.83056(17) 0.30126(12) 0.0189(3) Uani 1 1 d . . . . .
H3 H 0.123613 0.821945 0.253765 0.023 Uiso 1 1 calc R U . . .
C4 C 0.4840(3) 0.92677(18) 0.26923(12) 0.0198(3) Uani 1 1 d . . . . .
H4 H 0.495911 0.983803 0.200082 0.024 Uiso 1 1 calc R U . . .
C11 C 0.7559(2) 0.72694(18) 1.03060(11) 0.0174(3) Uani 1 1 d . . . . .
H11A H 0.818074 0.822656 1.083948 0.026 Uiso 1 1 calc R U . . .
H11B H 0.746220 0.620700 1.069036 0.026 Uiso 1 1 calc R U . . .
H11C H 0.595293 0.731880 1.002252 0.026 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4464(10) . ?
S1 O3 1.4497(10) . ?
S1 C10 1.7759(13) . ?
S1 C11 1.7644(13) . ?
O1 C7 1.2231(16) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.5103(18) . ?
C8 C9 1.5265(17) . ?
C1 C7 1.4981(18) . ?
C1 C6 1.3972(19) . ?
C1 C2 1.3983(18) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5320(17) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C6 H6 0.9500 . ?
C6 C5 1.3906(19) . ?
C5 H5 0.9500 . ?
C5 C4 1.388(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.389(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.394(2) . ?
C4 H4 0.9500 . ?
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
O2 S1 O3 117.64(6) . . ?
O2 S1 C10 109.66(6) . . ?
O2 S1 C11 108.26(6) . . ?
O3 S1 C10 107.13(6) . . ?
O3 S1 C11 108.00(6) . . ?
C11 S1 C10 105.49(6) . . ?
H8A C8 H8B 107.8 . . ?
C7 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
C7 C8 C9 112.80(10) . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C6 C1 C7 121.90(12) . . ?
C6 C1 C2 119.32(12) . . ?
C2 C1 C7 118.78(12) . . ?
O1 C7 C8 121.00(12) . . ?
O1 C7 C1 120.43(12) . . ?
C1 C7 C8 118.58(11) . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
C8 C9 C10 112.47(10) . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
S1 C10 H10A 108.5 . . ?
S1 C10 H10B 108.5 . . ?
C9 C10 S1 114.89(9) . . ?
C9 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.26(13) . . ?
C5 C6 H6 119.9 . . ?
C6 C5 H5 119.9 . . ?
C4 C5 C6 120.22(13) . . ?
C4 C5 H5 119.9 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.19(13) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.22(13) . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 119.80(13) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
S1 C11 H11A 109.5 . . ?
S1 C11 H11B 109.5 . . ?
S1 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
O2 S1 C10 C9 -44.24(11) . . . . ?
O3 S1 C10 C9 -172.97(9) . . . . ?
C8 C9 C10 S1 82.93(12) . . . . ?
C1 C6 C5 C4 -0.2(2) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C7 C8 C9 C10 174.03(10) . . . . ?
C7 C1 C6 C5 -178.81(12) . . . . ?
C7 C1 C2 C3 178.88(12) . . . . ?
C9 C8 C7 O1 1.48(18) . . . . ?
C9 C8 C7 C1 -178.26(10) . . . . ?
C6 C1 C7 O1 174.48(12) . . . . ?
C6 C1 C7 C8 -5.78(18) . . . . ?
C6 C1 C2 C3 -0.39(19) . . . . ?
C6 C5 C4 C3 0.0(2) . . . . ?
C2 C1 C7 O1 -4.77(19) . . . . ?
C2 C1 C7 C8 174.97(11) . . . . ?
C2 C1 C6 C5 0.44(19) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C11 S1 C10 C9 72.13(10) . . . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.256
_oxdiff_exptl_absorpt_empirical_full_min 0.754
####################################################################### 
# 
# 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_hpd130b
_database_code_depnum_ccdc_archive 'CCDC 2042737'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman'
;University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2020-11-05 deposited with the CCDC.	2022-03-21 downloaded from the CCDC.
;
_audit_creation_date             2020-06-23
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H11 F O3 S'
_chemical_formula_sum            'C10 H11 F O3 S'
_chemical_formula_weight         230.25
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O S F'
_chemical_oxdiff_usercomment     'K44-9 FLou'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   5.71650(10)
_cell_length_b                   12.1828(2)
_cell_length_c                   14.7356(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.7220(10)
_cell_angle_gamma                90
_cell_volume                     1025.77(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14719
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.3720
_cell_measurement_theta_min      3.6020
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.841
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.763
_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    1.491
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             480
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 1 0 0.0649
0 6 6 0.0302
0 -2 -9 0.0272
4 0 -1 0.0776
0 -6 -6 0.0207
0 2 9 0.0154
0 8 -2 0.0300

_exptl_crystal_size_max          0.166
_exptl_crystal_size_mid          0.099
_exptl_crystal_size_min          0.045
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
-3.6660 1.1598 -0.2010 0.0509 0.2042 -0.9776
0.0107 6.1239 6.0450 0.2315 0.9637 0.1329
-0.3225 -2.0390 -9.1738 0.3682 -0.8909 -0.2661
3.6985 -0.3744 -0.9287 0.0997 -0.2364 0.9665
0.1132 -6.1433 -6.0187 -0.2324 -0.9675 -0.0995
0.1992 2.0511 9.2027 -0.3714 0.8986 0.2338
0.3716 7.6216 -2.3934 0.9216 0.3815 0.0713

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22324
_diffrn_reflns_point_group_measured_fraction_full 0.798
_diffrn_reflns_point_group_measured_fraction_max 0.752
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.622
_diffrn_reflns_theta_min         3.628
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -91.00 -16.00   0.50    0.06    --  -46.87 131.00-107.00  150
  2  ω   -120.00 -70.00   0.50    0.06    --  -46.87-131.00-177.00  100
  3  ω    -95.00 -19.00   0.50    0.06    --  -46.87 137.00  69.00  152
  4  ω   -120.00 -66.00   0.50    0.06    --  -46.87-137.00   6.00  108
  5  ω     38.00  99.00   0.50    0.06    --   46.87-131.00-177.00  122
  6  ω    -90.00 -16.00   0.50    0.24    --  -88.50 131.00-107.00  148
  7  ω   -160.00 -70.00   0.50    0.24    --  -88.50-131.00-177.00  180
  8  ω    -95.00 -19.00   0.50    0.24    --  -88.50 137.00  69.00  152
  9  ω     41.00 120.00   0.50    0.24    --  106.69-137.00   6.00  158
 10  ω     87.00 178.00   0.50    0.24    --  106.69 137.00  69.00  182
 11  ω     38.00 116.00   0.50    0.24    --  106.69-131.00-177.00  156
 12  ω     91.00 178.00   0.50    0.24    --  106.69 131.00-107.00  174
 13  ω   -120.00 -87.00   0.50    0.06    --  -46.87-125.00 -60.00   66
 14  ω   -120.00 -83.00   0.50    0.06    --  -46.87 -57.00   0.00   74
 15  ω   -120.00 -83.00   0.50    0.06    --  -46.87 -57.00 -90.00   74
 16  ω     83.00 120.00   0.50    0.06    --   46.87  57.00 120.00   74
 17  ω     41.00 102.00   0.50    0.06    --   46.87-137.00   6.00  122
 18  ω    -51.00 -16.00   0.50    0.24    --  -88.50  45.00 120.00   70
 19  ω   -160.00 -91.00   0.50    0.24    --  -88.50 -61.00 -90.00  138
 20  ω    -51.00 -16.00   0.50    0.24    --  -88.50  45.00  30.00   70
 21  ω    -51.00 -16.00   0.50    0.24    --  -88.50  45.00  60.00   70
 22  ω     92.00 178.00   0.50    0.24    --  106.69  45.00   0.00  172
 23  ω     34.00 105.00   0.50    0.24    --  106.69 -94.00-150.00  142
 24  ω     34.00  71.00   0.50    0.24    --  106.69 -61.00-120.00   74
 25  ω     34.00  71.00   0.50    0.24    --  106.69 -61.00-180.00   74
 26  ω     34.00  71.00   0.50    0.24    --  106.69 -61.00 -60.00   74
 27  ω     95.00 178.00   0.50    0.24    --  106.69 125.00 -60.00  166
 28  ω     34.00 101.00   0.50    0.24    --  106.69 -77.00 150.00  134
 29  ω   -121.00 -32.00   0.50    0.06    --  -46.87 -37.00 -60.00  178
 30  ω   -121.00 -32.00   0.50    0.06    --  -46.87 -37.00 150.00  178
 31  ω   -121.00 -56.00   0.50    0.06    --  -46.87 -37.00-150.00  130
 32  ω   -121.00 -32.00   0.50    0.06    --  -46.87 -37.00  60.00  178
 33  ω     53.00  78.00   0.50    0.24    --  106.69-132.00-177.00   50
 34  ω   -118.00 -91.00   0.50    0.06    --  -46.87-125.00 120.00   54
 35  ω   -150.00-108.00   0.50    0.24    --  -88.50 -77.00  30.00   84
 36  ω    -41.00 -16.00   0.50    0.24    --  -88.50  45.00 -60.00   50
 37  ω   -158.00-109.00   0.50    0.24    --  -88.50 -94.00 -60.00   98
 38  ω    -51.00 -26.00   0.50    0.24    --  -88.50  45.00  90.00   50
 39  ω   -149.00-123.00   0.50    0.24    --  -88.50 -77.00-120.00   52
 40  ω     34.00  59.00   0.50    0.24    --  106.69 -61.00  90.00   50
 41  ω     47.00 100.00   0.50    0.24    --  106.69 -77.00 -30.00  106
 42  ω     36.00 111.00   0.50    0.24    --  106.69-125.00  90.00  150
 43  ω    149.00 175.00   0.50    0.24    --  106.69  45.00-120.00   52
 44  ω     76.00 101.00   0.50    0.24    --  106.69 -77.00-150.00   50
 45  ω     98.00 125.00   0.50    0.24    --  106.69  45.00-120.00   54
 46  ω     34.00  59.00   0.50    0.24    --  106.69 -61.00-150.00   50
 47  ω     34.00  60.00   0.50    0.24    --  106.69 -61.00  60.00   52
 48  ω     34.00  68.00   0.50    0.24    --  106.69 -61.00   0.00   68
 49  ω   -119.00 -94.00   0.50    0.06    --  -46.87-132.00-177.00   50
 50  ω   -121.00 -32.00   0.50    0.06    --  -46.87 -37.00 120.00  178
 51  ω   -121.00 -32.00   0.50    0.06    --  -46.87 -37.00 -90.00  178
 52  ω   -121.00 -32.00   0.50    0.06    --  -46.87 -37.00   0.00  178
 53  ω   -121.00 -32.00   0.50    0.06    --  -46.87 -37.00-120.00  178
 54  ω   -120.00 -83.00   0.50    0.06    --  -46.87 -57.00 120.00   74
 55  ω     32.00 121.00   0.50    0.06    --   46.87  37.00  90.00  178
 56  ω     32.00 121.00   0.50    0.06    --   46.87  37.00 -60.00  178
 57  ω     32.00 121.00   0.50    0.06    --   46.87  37.00 -90.00  178
 58  ω     32.00 121.00   0.50    0.06    --   46.87  37.00-180.00  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0212245000
_diffrn_orient_matrix_UB_12      0.1000643000
_diffrn_orient_matrix_UB_13      -0.0631181000
_diffrn_orient_matrix_UB_21      -0.0356939000
_diffrn_orient_matrix_UB_22      0.0772927000
_diffrn_orient_matrix_UB_23      0.0811861000
_diffrn_orient_matrix_UB_31      0.2663755000
_diffrn_orient_matrix_UB_32      0.0023743000
_diffrn_orient_matrix_UB_33      0.0191126000
_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         0.540
_reflns_Friedel_fraction_full    0.595
_reflns_Friedel_fraction_max     0.530
_reflns_number_gt                3185
_reflns_number_total             3241
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Flack x determined using 1091 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.030(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3241
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0303
_refine_ls_restrained_S_all      1.021
_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)+(0.0528P)²+0.3443P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0802
_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 Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C2(H2A,H2B), C13(H13A,H13B), C1(H1A,H1B),
 C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C6(H6), C7(H7), C10(H10), C17(H17), C18(H18), C8(H8), C16(H16),
 C9(H9), C19(H19)
;
_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
S2 S 0.96734(11) 1.02137(5) 0.63392(5) 0.01881(17) Uani 1 1 d . . . . .
S1 S 0.47774(11) 1.09073(5) 0.36309(5) 0.01884(17) Uani 1 1 d . . . . .
F1 F 0.4407(3) 1.10184(15) 0.46708(13) 0.0286(4) Uani 1 1 d . . . . .
F2 F 0.9121(3) 1.03752(15) 0.53006(13) 0.0279(4) Uani 1 1 d . . . . .
O3 O -0.1481(4) 0.76735(17) 0.41750(15) 0.0237(5) Uani 1 1 d . . . . .
O6 O 0.3126(4) 0.69845(17) 0.56882(15) 0.0243(5) Uani 1 1 d . . . . .
O4 O 1.2050(4) 1.05120(19) 0.64711(16) 0.0265(5) Uani 1 1 d . . . . .
O2 O 0.2846(4) 1.14410(18) 0.32055(17) 0.0294(5) Uani 1 1 d . . . . .
O1 O 0.7069(4) 1.12901(18) 0.34844(16) 0.0270(5) Uani 1 1 d . . . . .
O5 O 0.7913(4) 1.07977(18) 0.67924(17) 0.0285(5) Uani 1 1 d . . . . .
C14 C 0.4801(5) 0.6499(2) 0.60394(19) 0.0177(6) Uani 1 1 d . . . . .
C11 C 0.9336(5) 0.8791(2) 0.6434(2) 0.0190(6) Uani 1 1 d . . . . .
H11A H 1.046842 0.843959 0.605230 0.023 Uiso 1 1 calc R U . . .
H11B H 0.971271 0.858194 0.705648 0.023 Uiso 1 1 calc R U . . .
C5 C -0.0003(6) 0.5952(2) 0.3739(2) 0.0161(6) Uani 1 1 d . . . . .
C20 C 0.6619(5) 0.4706(2) 0.6575(2) 0.0193(6) Uani 1 1 d . . . . .
H20 H 0.787989 0.509047 0.683128 0.023 Uiso 1 1 calc R U . . .
C12 C 0.6914(5) 0.8342(2) 0.6177(2) 0.0192(6) Uani 1 1 d . . . . .
H12A H 0.573487 0.869438 0.653670 0.023 Uiso 1 1 calc R U . . .
H12B H 0.654665 0.848008 0.554058 0.023 Uiso 1 1 calc R U . . .
C2 C 0.2345(6) 0.8970(2) 0.3809(2) 0.0206(6) Uani 1 1 d . . . . .
H2A H 0.221805 0.904562 0.446139 0.025 Uiso 1 1 calc R U . . .
H2B H 0.102832 0.934641 0.351832 0.025 Uiso 1 1 calc R U . . .
C15 C 0.4771(6) 0.5276(2) 0.61427(19) 0.0184(6) Uani 1 1 d . . . . .
C6 C -0.1902(5) 0.5398(2) 0.4083(2) 0.0195(6) Uani 1 1 d . . . . .
H6 H -0.310147 0.579392 0.434274 0.023 Uiso 1 1 calc R U . . .
C13 C 0.6955(5) 0.7114(2) 0.6362(2) 0.0199(6) Uani 1 1 d . . . . .
H13A H 0.830146 0.680044 0.607137 0.024 Uiso 1 1 calc R U . . .
H13B H 0.716809 0.700067 0.701038 0.024 Uiso 1 1 calc R U . . .
C7 C -0.2035(6) 0.4264(3) 0.4047(2) 0.0224(6) Uani 1 1 d . . . . .
H7 H -0.330769 0.390212 0.428778 0.027 Uiso 1 1 calc R U . . .
C4 C 0.0136(5) 0.7177(2) 0.38452(19) 0.0185(6) Uani 1 1 d . . . . .
C10 C 0.1763(5) 0.5352(2) 0.3324(2) 0.0193(6) Uani 1 1 d . . . . .
H10 H 0.302777 0.571305 0.307601 0.023 Uiso 1 1 calc R U . . .
C17 C 0.2825(6) 0.3548(3) 0.5836(2) 0.0222(6) Uani 1 1 d . . . . .
H17 H 0.155588 0.315849 0.559245 0.027 Uiso 1 1 calc R U . . .
C18 C 0.4673(6) 0.2995(2) 0.6251(2) 0.0222(6) Uani 1 1 d . . . . .
H18 H 0.464779 0.223280 0.628276 0.027 Uiso 1 1 calc R U . . .
C8 C -0.0262(6) 0.3667(2) 0.3649(2) 0.0216(6) Uani 1 1 d . . . . .
H8 H -0.033545 0.290473 0.362766 0.026 Uiso 1 1 calc R U . . .
C1 C 0.4626(5) 0.9480(2) 0.3510(2) 0.0187(6) Uani 1 1 d . . . . .
H1A H 0.483980 0.929734 0.287700 0.022 Uiso 1 1 calc R U . . .
H1B H 0.590941 0.915347 0.386008 0.022 Uiso 1 1 calc R U . . .
C16 C 0.2859(5) 0.4688(3) 0.5783(2) 0.0203(6) Uani 1 1 d . . . . .
H16 H 0.160631 0.505924 0.550806 0.024 Uiso 1 1 calc R U . . .
C9 C 0.1615(6) 0.4215(3) 0.3284(2) 0.0219(6) Uani 1 1 d . . . . .
H9 H 0.278827 0.381678 0.300958 0.026 Uiso 1 1 calc R U . . .
C19 C 0.6570(5) 0.3571(3) 0.6621(2) 0.0215(6) Uani 1 1 d . . . . .
H19 H 0.780902 0.319295 0.689934 0.026 Uiso 1 1 calc R U . . .
C3 C 0.2298(5) 0.7765(2) 0.3551(2) 0.0195(6) Uani 1 1 d . . . . .
H3A H 0.240104 0.770276 0.289724 0.023 Uiso 1 1 calc R U . . .
H3B H 0.366234 0.740681 0.382376 0.023 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
S2 F2 1.5657(19) . ?
S2 O4 1.414(2) . ?
S2 O5 1.416(2) . ?
S2 C11 1.750(3) . ?
S1 F1 1.5591(19) . ?
S1 O2 1.412(2) . ?
S1 O1 1.413(2) . ?
S1 C1 1.750(3) . ?
O3 C4 1.218(4) . ?
O6 C14 1.227(4) . ?
C14 C15 1.497(4) . ?
C14 C13 1.506(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.526(4) . ?
C5 C6 1.387(4) . ?
C5 C4 1.501(4) . ?
C5 C10 1.402(4) . ?
C20 H20 0.9300 . ?
C20 C15 1.401(4) . ?
C20 C19 1.386(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.520(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.522(4) . ?
C2 C3 1.517(4) . ?
C15 C16 1.398(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.385(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C7 H7 0.9300 . ?
C7 C8 1.392(5) . ?
C4 C3 1.504(4) . ?
C10 H10 0.9300 . ?
C10 C9 1.389(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.380(5) . ?
C17 C16 1.391(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.389(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.386(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C16 H16 0.9300 . ?
C9 H9 0.9300 . ?
C19 H19 0.9300 . ?
C3 H3A 0.9700 . ?
C3 H3B 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
F2 S2 C11 100.55(13) . . ?
O4 S2 F2 105.47(12) . . ?
O4 S2 O5 119.97(15) . . ?
O4 S2 C11 110.56(15) . . ?
O5 S2 F2 105.82(14) . . ?
O5 S2 C11 112.23(14) . . ?
F1 S1 C1 100.30(13) . . ?
O2 S1 F1 105.60(13) . . ?
O2 S1 O1 119.76(15) . . ?
O2 S1 C1 112.12(15) . . ?
O1 S1 F1 105.98(12) . . ?
O1 S1 C1 110.84(14) . . ?
O6 C14 C15 120.7(3) . . ?
O6 C14 C13 120.9(3) . . ?
C15 C14 C13 118.3(2) . . ?
S2 C11 H11A 108.3 . . ?
S2 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
C12 C11 S2 115.9(2) . . ?
C12 C11 H11A 108.3 . . ?
C12 C11 H11B 108.3 . . ?
C6 C5 C4 119.0(3) . . ?
C6 C5 C10 119.2(3) . . ?
C10 C5 C4 121.8(3) . . ?
C15 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C15 120.1(3) . . ?
C11 C12 H12A 110.2 . . ?
C11 C12 H12B 110.2 . . ?
H12A C12 H12B 108.5 . . ?
C13 C12 C11 107.4(2) . . ?
C13 C12 H12A 110.2 . . ?
C13 C12 H12B 110.2 . . ?
H2A C2 H2B 108.3 . . ?
C1 C2 H2A 109.8 . . ?
C1 C2 H2B 109.8 . . ?
C3 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
C3 C2 C1 109.3(2) . . ?
C20 C15 C14 121.9(3) . . ?
C16 C15 C14 118.9(3) . . ?
C16 C15 C20 119.2(3) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 121.0(3) . . ?
C7 C6 H6 119.5 . . ?
C14 C13 C12 115.2(2) . . ?
C14 C13 H13A 108.5 . . ?
C14 C13 H13B 108.5 . . ?
C12 C13 H13A 108.5 . . ?
C12 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C8 119.8(3) . . ?
C8 C7 H7 120.1 . . ?
O3 C4 C5 119.8(3) . . ?
O3 C4 C3 121.2(3) . . ?
C5 C4 C3 119.0(3) . . ?
C5 C10 H10 120.2 . . ?
C9 C10 C5 119.7(3) . . ?
C9 C10 H10 120.2 . . ?
C18 C17 H17 120.0 . . ?
C18 C17 C16 120.0(3) . . ?
C16 C17 H17 120.0 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.4(3) . . ?
C19 C18 H18 119.8 . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.6(3) . . ?
C9 C8 H8 120.2 . . ?
S1 C1 H1A 108.6 . . ?
S1 C1 H1B 108.6 . . ?
C2 C1 S1 114.6(2) . . ?
C2 C1 H1A 108.6 . . ?
C2 C1 H1B 108.6 . . ?
H1A C1 H1B 107.6 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.2(3) . . ?
C17 C16 H16 119.9 . . ?
C10 C9 H9 119.6 . . ?
C8 C9 C10 120.7(3) . . ?
C8 C9 H9 119.6 . . ?
C20 C19 C18 120.1(3) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C4 C3 C2 113.4(2) . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?

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
S2 C11 C12 C13 -176.6(2) . . . . ?
F1 S1 C1 C2 58.5(2) . . . . ?
F2 S2 C11 C12 -60.8(2) . . . . ?
O3 C4 C3 C2 6.8(4) . . . . ?
O6 C14 C15 C20 -177.3(3) . . . . ?
O6 C14 C15 C16 3.8(4) . . . . ?
O6 C14 C13 C12 -2.7(4) . . . . ?
O4 S2 C11 C12 -171.8(2) . . . . ?
O2 S1 C1 C2 -53.1(3) . . . . ?
O1 S1 C1 C2 170.2(2) . . . . ?
O5 S2 C11 C12 51.3(3) . . . . ?
C14 C15 C16 C17 177.4(3) . . . . ?
C11 C12 C13 C14 -172.7(2) . . . . ?
C5 C6 C7 C8 -0.9(5) . . . . ?
C5 C4 C3 C2 -172.4(3) . . . . ?
C5 C10 C9 C8 0.1(5) . . . . ?
C20 C15 C16 C17 -1.5(4) . . . . ?
C15 C14 C13 C12 176.2(2) . . . . ?
C15 C20 C19 C18 -1.0(5) . . . . ?
C6 C5 C4 O3 -4.9(4) . . . . ?
C6 C5 C4 C3 174.3(3) . . . . ?
C6 C5 C10 C9 -1.6(4) . . . . ?
C6 C7 C8 C9 -0.6(5) . . . . ?
C13 C14 C15 C20 3.8(4) . . . . ?
C13 C14 C15 C16 -175.1(3) . . . . ?
C7 C8 C9 C10 1.0(5) . . . . ?
C4 C5 C6 C7 -176.3(3) . . . . ?
C4 C5 C10 C9 176.6(3) . . . . ?
C10 C5 C6 C7 2.0(4) . . . . ?
C10 C5 C4 O3 176.9(3) . . . . ?
C10 C5 C4 C3 -3.9(4) . . . . ?
C17 C18 C19 C20 0.0(5) . . . . ?
C18 C17 C16 C15 0.5(4) . . . . ?
C1 C2 C3 C4 178.2(2) . . . . ?
C16 C17 C18 C19 0.3(5) . . . . ?
C19 C20 C15 C14 -177.1(3) . . . . ?
C19 C20 C15 C16 1.8(4) . . . . ?
C3 C2 C1 S1 172.3(2) . . . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.390
_oxdiff_exptl_absorpt_empirical_full_min 0.807
####################################################################### 
# 
# 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_hpd243
_database_code_depnum_ccdc_archive 'CCDC 2042734'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman'
;University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2020-11-05 deposited with the CCDC.	2022-03-21 downloaded from the CCDC.
;
_audit_creation_date             2020-10-29
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H27 N O6 S'
_chemical_formula_sum            'C15 H27 N O6 S'
_chemical_formula_weight         349.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         'CH N O S'
_chemical_oxdiff_usercomment     'VNY 384-AOI'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.1742(3)
_cell_length_b                   16.6182(3)
_cell_length_c                   10.3665(3)
_cell_angle_alpha                90
_cell_angle_beta                 116.394(3)
_cell_angle_gamma                90
_cell_volume                     1724.34(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6987
_cell_measurement_temperature    99.9(2)
_cell_measurement_theta_max      75.7630
_cell_measurement_theta_min      5.1450
_shelx_estimated_absorpt_T_max   0.921
_shelx_estimated_absorpt_T_min   0.542
_exptl_absorpt_coefficient_mu    1.933
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.394
_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    1.346
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             752
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 0 -7 0.1464
-2 -10 0 0.0095
-1 11 1 0.0521
-2 -10 -1 0.0112
-2 1 7 0.1433
4 9 -1 0.0142
4 8 0 0.0160

_exptl_crystal_size_max          0.361
_exptl_crystal_size_mid          0.231
_exptl_crystal_size_min          0.043
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2.3822 -0.0138 -6.6755 0.0264 0.9851 0.1701
-2.3336 -10.1640 0.4067 -0.0032 -0.1873 0.9823
-0.5350 10.6523 1.0643 0.3506 -0.0076 -0.9365
-1.8549 -10.0479 -0.7934 -0.0021 -0.0089 1.0000
-2.1427 1.0525 6.6121 -0.0250 -0.9627 -0.2695
4.2378 8.7324 -1.4209 -0.2598 0.3069 -0.9156
4.1248 8.4255 -0.1505 -0.3236 0.1129 -0.9394

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16571
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.519
_diffrn_reflns_theta_min         4.417
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -35.00  29.00   0.50    0.12    --  -46.62  28.00 104.00  128
  2  ω    -51.00 -16.00   0.50    0.48    --  -88.50  45.00 150.00   70
  3  ω    -71.00 -15.00   0.50    0.48    --  -88.50  61.00  90.00  112
  4  ω    -71.00 -15.00   0.50    0.48    --  -88.50  61.00 -90.00  112
  5  ω    -30.00  29.00   0.50    0.12    --  -46.62  19.00-120.00  118
  6  ω    -51.00 -16.00   0.50    0.48    --  -88.50  45.00-180.00   70
  7  ω   -122.00 -32.00   0.50    0.12    --  -46.62 -28.00 -56.00  180
  8  ω     33.00 123.00   0.50    0.12    --   46.62  28.00 104.00  180
  9  ω     92.00 178.00   0.50    0.48    --  106.69  28.00 104.00  172
 10  ω     95.00 178.00   0.50    0.48    --  106.69 125.00 -60.00  166
 11  ω     89.00 178.00   0.50    0.48    --  106.69  15.00-120.00  178
 12  ω     34.00  71.00   0.50    0.48    --  106.69 -61.00  30.00   74
 13  ω     34.00  71.00   0.50    0.48    --  106.69 -61.00 -30.00   74
 14  ω     34.00  71.00   0.50    0.48    --  106.69 -61.00 -60.00   74
 15  ω     34.00  71.00   0.50    0.48    --  106.69 -61.00   0.00   74
 16  ω     34.00 101.00   0.50    0.48    --  106.69 -77.00 120.00  134
 17  ω     34.00  71.00   0.50    0.48    --  106.69 -61.00 150.00   74
 18  ω    -28.00  35.00   0.50    0.12    --   46.62 -28.00 -56.00  126
 19  ω     34.00  71.00   0.50    0.48    --  106.69 -61.00-150.00   74
 20  ω     34.00 101.00   0.50    0.48    --  106.69 -77.00-150.00  134
 21  ω     34.00  71.00   0.50    0.48    --  106.69 -61.00-120.00   74
 22  ω   -119.00 -87.00   0.50    0.12    --  -46.62-125.00  60.00   64
 23  ω   -119.00 -83.00   0.50    0.12    --  -46.62 -57.00 -60.00   72
 24  ω   -163.00 -73.00   0.50    0.48    --  -88.50 -28.00 -56.00  180
 25  ω   -160.00-100.00   0.50    0.48    --  -88.50 -94.00  60.00  120
;
_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      -0.1442205000
_diffrn_orient_matrix_UB_12      0.0312112000
_diffrn_orient_matrix_UB_13      -0.0554897000
_diffrn_orient_matrix_UB_21      -0.0065618000
_diffrn_orient_matrix_UB_22      0.0139365000
_diffrn_orient_matrix_UB_23      -0.1499355000
_diffrn_orient_matrix_UB_31      -0.0533685000
_diffrn_orient_matrix_UB_32      -0.0861659000
_diffrn_orient_matrix_UB_33      -0.0443432000
_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                3130
_reflns_number_total             3515
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT n/a (Sheldrick, 2015)'
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0009(2)
_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   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3515
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0386
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0516P)²+0.8182P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1057
_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:
 C8(H8), C1(H1A)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C2(H2A,H2B), C4(H4A,H4B), C6(H6A,H6B), C5(H5A,H5B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C10(H10A,H10B,H10C), C14(H14A,H14B,H14C), C13(H13A,H13B,
 H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.61249(4) 0.17312(2) 0.58095(4) 0.01866(13) Uani 1 1 d . . . . .
O4 O 0.61121(11) 0.39147(7) 0.58814(11) 0.0220(3) Uani 1 1 d . . . . .
O5 O 1.10138(11) 0.21801(7) 0.72178(11) 0.0203(2) Uani 1 1 d . . . . .
O2 O 0.57269(11) 0.21985(7) 0.67327(12) 0.0233(3) Uani 1 1 d . . . . .
O6 O 0.96614(11) 0.26726(7) 0.49739(11) 0.0210(3) Uani 1 1 d . . . . .
O3 O 0.79082(11) 0.37022(7) 0.80040(11) 0.0238(3) Uani 1 1 d . . . . .
O1 O 0.51173(11) 0.12572(7) 0.46776(12) 0.0254(3) Uani 1 1 d . . . . .
N1 N 0.90629(13) 0.27171(8) 0.67960(14) 0.0194(3) Uani 1 1 d . . . . .
H1 H 0.929337 0.263523 0.771504 0.023 Uiso 1 1 calc R U . . .
C7 C 0.67515(16) 0.24155(10) 0.49334(16) 0.0196(3) Uani 1 1 d . . . . .
H7A H 0.716735 0.209542 0.443453 0.024 Uiso 1 1 calc R U . . .
H7B H 0.597934 0.270190 0.418208 0.024 Uiso 1 1 calc R U . . .
C8 C 0.77715(15) 0.30516(9) 0.58589(16) 0.0187(3) Uani 1 1 d . . . . .
H8 H 0.791601 0.341630 0.517356 0.022 Uiso 1 1 calc R U . . .
C1 C 0.74513(15) 0.10805(10) 0.69515(16) 0.0194(3) Uani 1 1 d . . . . .
H1A H 0.812087 0.140941 0.775673 0.023 Uiso 1 1 calc R U . . .
C15 C 1.26744(17) 0.26565(11) 0.6445(2) 0.0277(4) Uani 1 1 d . . . . .
H15A H 1.199567 0.288852 0.554894 0.042 Uiso 1 1 calc R U . . .
H15B H 1.345167 0.249240 0.630633 0.042 Uiso 1 1 calc R U . . .
H15C H 1.294800 0.305880 0.721487 0.042 Uiso 1 1 calc R U . . .
C2 C 0.81673(16) 0.06659(10) 0.61725(17) 0.0217(3) Uani 1 1 d . . . . .
H2A H 0.855316 0.107524 0.577209 0.026 Uiso 1 1 calc R U . . .
H2B H 0.752271 0.033763 0.536580 0.026 Uiso 1 1 calc R U . . .
C4 C 0.87171(18) -0.04905(10) 0.79141(18) 0.0261(4) Uani 1 1 d . . . . .
H4A H 0.945833 -0.081376 0.863170 0.031 Uiso 1 1 calc R U . . .
H4B H 0.810881 -0.086015 0.715797 0.031 Uiso 1 1 calc R U . . .
C6 C 0.68464(16) 0.04605(10) 0.75953(17) 0.0228(3) Uani 1 1 d . . . . .
H6A H 0.640028 0.074110 0.810548 0.027 Uiso 1 1 calc R U . . .
H6B H 0.617016 0.013145 0.681580 0.027 Uiso 1 1 calc R U . . .
C5 C 0.79574(17) -0.00826(10) 0.86469(17) 0.0251(4) Uani 1 1 d . . . . .
H5A H 0.858636 0.024276 0.946915 0.030 Uiso 1 1 calc R U . . .
H5B H 0.756394 -0.049825 0.902728 0.030 Uiso 1 1 calc R U . . .
C10 C 0.55012(17) 0.43598(10) 0.66363(18) 0.0254(4) Uani 1 1 d . . . . .
H10A H 0.468638 0.462335 0.593572 0.038 Uiso 1 1 calc R U . . .
H10B H 0.612801 0.476768 0.725266 0.038 Uiso 1 1 calc R U . . .
H10C H 0.527610 0.398927 0.723108 0.038 Uiso 1 1 calc R U . . .
C3 C 0.92800(17) 0.01265(10) 0.72386(18) 0.0238(3) Uani 1 1 d . . . . .
H3A H 0.972692 -0.015602 0.673117 0.029 Uiso 1 1 calc R U . . .
H3B H 0.995526 0.046276 0.800538 0.029 Uiso 1 1 calc R U . . .
C14 C 1.15954(18) 0.12871(11) 0.56909(19) 0.0298(4) Uani 1 1 d . . . . .
H14A H 1.120916 0.084121 0.599941 0.045 Uiso 1 1 calc R U . . .
H14B H 1.234087 0.108762 0.552528 0.045 Uiso 1 1 calc R U . . .
H14C H 1.091150 0.151825 0.479724 0.045 Uiso 1 1 calc R U . . .
C12 C 1.20989(16) 0.19293(10) 0.68548(17) 0.0212(3) Uani 1 1 d . . . . .
C13 C 1.31175(17) 0.15731(12) 0.82648(18) 0.0277(4) Uani 1 1 d . . . . .
H13A H 1.340724 0.198680 0.901645 0.042 Uiso 1 1 calc R U . . .
H13B H 1.389057 0.137843 0.814611 0.042 Uiso 1 1 calc R U . . .
H13C H 1.271259 0.112393 0.854241 0.042 Uiso 1 1 calc R U . . .
C11 C 0.99130(15) 0.25318(9) 0.62256(16) 0.0181(3) Uani 1 1 d . . . . .
C9 C 0.72907(15) 0.35810(9) 0.67290(16) 0.0180(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4475(11) . ?
S1 O1 1.4458(12) . ?
S1 C7 1.7815(16) . ?
S1 C1 1.7909(16) . ?
O4 C10 1.4493(18) . ?
O4 C9 1.3361(18) . ?
O5 C12 1.4803(18) . ?
O5 C11 1.3370(19) . ?
O6 C11 1.2220(19) . ?
O3 C9 1.2054(19) . ?
N1 H1 0.8800 . ?
N1 C8 1.445(2) . ?
N1 C11 1.3587(19) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.538(2) . ?
C8 H8 1.0000 . ?
C8 C9 1.519(2) . ?
C1 H1A 1.0000 . ?
C1 C2 1.530(2) . ?
C1 C6 1.538(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C15 C12 1.516(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.533(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.527(2) . ?
C4 C3 1.526(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C5 1.530(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C14 C12 1.519(2) . ?
C12 C13 1.518(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 C7 107.49(7) . . ?
O2 S1 C1 107.10(7) . . ?
O1 S1 O2 118.14(7) . . ?
O1 S1 C7 105.95(7) . . ?
O1 S1 C1 108.95(7) . . ?
C7 S1 C1 108.97(7) . . ?
C9 O4 C10 114.83(12) . . ?
C11 O5 C12 120.33(11) . . ?
C8 N1 H1 120.8 . . ?
C11 N1 H1 120.8 . . ?
C11 N1 C8 118.49(13) . . ?
S1 C7 H7A 107.8 . . ?
S1 C7 H7B 107.8 . . ?
H7A C7 H7B 107.1 . . ?
C8 C7 S1 118.10(10) . . ?
C8 C7 H7A 107.8 . . ?
C8 C7 H7B 107.8 . . ?
N1 C8 C7 113.36(13) . . ?
N1 C8 H8 106.4 . . ?
N1 C8 C9 109.55(12) . . ?
C7 C8 H8 106.4 . . ?
C9 C8 C7 114.13(12) . . ?
C9 C8 H8 106.4 . . ?
S1 C1 H1A 108.3 . . ?
C2 C1 S1 113.34(10) . . ?
C2 C1 H1A 108.3 . . ?
C2 C1 C6 111.17(13) . . ?
C6 C1 S1 107.29(11) . . ?
C6 C1 H1A 108.3 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
C1 C2 H2A 109.8 . . ?
C1 C2 H2B 109.8 . . ?
C1 C2 C3 109.25(13) . . ?
H2A C2 H2B 108.3 . . ?
C3 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
H4A C4 H4B 108.0 . . ?
C5 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
C3 C4 C5 111.33(14) . . ?
C1 C6 H6A 109.8 . . ?
C1 C6 H6B 109.8 . . ?
H6A C6 H6B 108.3 . . ?
C5 C6 C1 109.30(13) . . ?
C5 C6 H6A 109.8 . . ?
C5 C6 H6B 109.8 . . ?
C4 C5 C6 111.22(13) . . ?
C4 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
C6 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
O4 C10 H10A 109.5 . . ?
O4 C10 H10B 109.5 . . ?
O4 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C4 C3 C2 110.86(14) . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
O5 C12 C15 110.13(13) . . ?
O5 C12 C14 110.11(13) . . ?
O5 C12 C13 102.32(12) . . ?
C15 C12 C14 113.02(14) . . ?
C15 C12 C13 110.54(14) . . ?
C13 C12 C14 110.20(14) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O5 C11 N1 110.27(13) . . ?
O6 C11 O5 126.82(14) . . ?
O6 C11 N1 122.91(14) . . ?
O4 C9 C8 110.81(12) . . ?
O3 C9 O4 124.62(14) . . ?
O3 C9 C8 124.53(14) . . ?

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 N1 70.23(15) . . . . ?
S1 C7 C8 C9 -56.14(16) . . . . ?
S1 C1 C2 C3 179.92(11) . . . . ?
S1 C1 C6 C5 -176.91(11) . . . . ?
O2 S1 C7 C8 48.05(13) . . . . ?
O2 S1 C1 C2 -168.66(11) . . . . ?
O2 S1 C1 C6 68.24(11) . . . . ?
O1 S1 C7 C8 175.22(11) . . . . ?
O1 S1 C1 C2 62.50(13) . . . . ?
O1 S1 C1 C6 -60.61(12) . . . . ?
N1 C8 C9 O4 178.44(12) . . . . ?
N1 C8 C9 O3 0.5(2) . . . . ?
C7 S1 C1 C2 -52.67(13) . . . . ?
C7 S1 C1 C6 -175.77(10) . . . . ?
C7 C8 C9 O4 -53.22(17) . . . . ?
C7 C8 C9 O3 128.83(16) . . . . ?
C8 N1 C11 O5 -175.74(13) . . . . ?
C8 N1 C11 O6 3.8(2) . . . . ?
C1 S1 C7 C8 -67.69(13) . . . . ?
C1 C2 C3 C4 57.36(17) . . . . ?
C1 C6 C5 C4 -56.40(17) . . . . ?
C2 C1 C6 C5 58.65(16) . . . . ?
C6 C1 C2 C3 -59.14(16) . . . . ?
C5 C4 C3 C2 -56.32(18) . . . . ?
C10 O4 C9 O3 -8.5(2) . . . . ?
C10 O4 C9 C8 173.51(13) . . . . ?
C3 C4 C5 C6 56.01(18) . . . . ?
C12 O5 C11 O6 1.1(2) . . . . ?
C12 O5 C11 N1 -179.39(13) . . . . ?
C11 O5 C12 C15 62.20(18) . . . . ?
C11 O5 C12 C14 -63.09(18) . . . . ?
C11 O5 C12 C13 179.75(13) . . . . ?
C11 N1 C8 C7 79.38(17) . . . . ?
C11 N1 C8 C9 -151.86(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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.752
_oxdiff_exptl_absorpt_empirical_full_min 0.572
####################################################################### 
# 
# 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_hpd241
_database_code_depnum_ccdc_archive 'CCDC 2042735'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman'
;University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2020-11-05 deposited with the CCDC.	2022-03-21 downloaded from the CCDC.
;
_audit_creation_date             2020-10-27
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H18 O4 S2'
_chemical_formula_sum            'C10 H18 O4 S2'
_chemical_formula_weight         266.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S'
_chemical_oxdiff_usercomment     'VNY 383-22'
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.09765(6)
_cell_length_b                   8.92648(10)
_cell_length_c                   22.0926(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.4743(9)
_cell_angle_gamma                90
_cell_volume                     1202.12(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12532
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.0320
_cell_measurement_theta_min      4.0050
_shelx_estimated_absorpt_T_max   0.795
_shelx_estimated_absorpt_T_min   0.475
_exptl_absorpt_coefficient_mu    4.015
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.454
_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    1.472
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 4 -1 0.1025
-2 4 -6 0.1072
-3 -4 0 0.0564
2 -5 6 0.0374
3 3 -4 0.1189
0 0 -14 0.0356
-3 -3 4 0.0455
0 0 14 0.0187

_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.169
_exptl_crystal_size_min          0.06
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2.5677 4.4071 -0.7430 0.0634 0.2563 0.9645
-2.3547 3.9932 -5.7033 0.2321 0.9660 -0.1136
-2.9744 -3.8213 -0.1596 -0.0270 -0.1050 -0.9941
1.8697 -4.5380 5.6151 -0.2336 -0.9715 -0.0410
3.1079 3.2458 -4.0984 0.3334 0.0600 0.9409
0.0538 0.0472 -14.3414 0.9814 0.1817 -0.0615
-3.1095 -3.2475 4.0718 -0.3316 -0.0596 -0.9415
-0.2230 -0.2241 14.3259 -0.9833 -0.1819 0.0089

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            21860
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.571
_diffrn_reflns_theta_min         4.003
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00  26.00   0.50    0.05    --  -46.62  73.00 -18.00  190
  2  ω    -25.00  69.00   0.50    0.05    --   46.62 -73.00-147.00  188
  3  ω     25.00 120.00   0.50    0.05    --   46.62  73.00 -18.00  190
  4  ω    -91.00 -15.00   0.50    0.06    --  -88.50  73.00 -18.00  152
  5  ω     34.00  91.00   0.50    0.06    --  106.69 -73.00-147.00  114
  6  ω     85.00 178.00   0.50    0.06    --  106.69  73.00 -18.00  186
  7  ω   -119.00 -24.00   0.50    0.05    --  -46.62 -73.00-147.00  190
  8  ω   -120.00 -32.00   0.50    0.05    --  -46.62 -37.00   0.00  176
  9  ω   -119.00 -87.00   0.50    0.05    --  -46.62-125.00 -90.00   64
 10  ω   -119.00 -87.00   0.50    0.05    --  -46.62-125.00 -60.00   64
 11  ω    -30.00  29.00   0.50    0.05    --  -46.62  19.00   0.00  118
 12  ω     83.00 120.00   0.50    0.05    --   46.62  57.00  30.00   74
 13  ω   -163.00 -73.00   0.50    0.06    --  -88.50 -30.00  60.00  180
 14  ω   -164.00 -71.00   0.50    0.06    --  -88.50 -15.00  90.00  186
 15  ω    -51.00 -16.00   0.50    0.06    --  -88.50  45.00 120.00   70
 16  ω   -160.00 -91.00   0.50    0.06    --  -88.50 -61.00 -60.00  138
 17  ω   -160.00-101.00   0.50    0.06    --  -88.50 -77.00 -30.00  118
 18  ω    -51.00 -16.00   0.50    0.06    --  -88.50  45.00 -30.00   70
 19  ω    -51.00 -16.00   0.50    0.06    --  -88.50  45.00 -90.00   70
 20  ω   -160.00 -66.00   0.50    0.06    --  -88.50 -73.00-147.00  188
 21  ω   -160.00 -91.00   0.50    0.06    --  -88.50 -61.00 120.00  138
 22  ω   -160.00 -91.00   0.50    0.06    --  -88.50 -61.00-180.00  138
 23  ω     95.00 178.00   0.50    0.06    --  106.69 125.00  60.00  166
 24  ω     34.00 105.00   0.50    0.06    --  106.69 -94.00-180.00  142
 25  ω     91.00 178.00   0.50    0.06    --  106.69  61.00 -60.00  174
 26  ω     34.00  71.00   0.50    0.06    --  106.69 -61.00 120.00   74
 27  ω    101.00 178.00   0.50    0.06    --  106.69  77.00  30.00  154
 28  ω     34.00 101.00   0.50    0.06    --  106.69 -77.00-180.00  134
 29  ω     34.00  71.00   0.50    0.06    --  106.69 -61.00 -30.00   74
 30  ω     34.00  71.00   0.50    0.06    --  106.69 -61.00  30.00   74
 31  ω     34.00 105.00   0.50    0.06    --  106.69 -94.00 150.00  142
 32  ω     91.00 178.00   0.50    0.06    --  106.69  61.00 120.00  174
 33  ω     34.00  71.00   0.50    0.06    --  106.69 -61.00   0.00   74
 34  ω   -120.00 -42.00   0.50    0.05    --  -46.62 -37.00  30.00  156
 35  ω   -120.00 -32.00   0.50    0.05    --  -46.62 -37.00-150.00  176
 36  ω   -120.00 -32.00   0.50    0.05    --  -46.62 -37.00  90.00  176
 37  ω   -120.00 -32.00   0.50    0.05    --  -46.62 -37.00 -90.00  176
 38  ω     83.00 120.00   0.50    0.05    --   46.62  57.00-120.00   74
 39  ω     32.00 121.00   0.50    0.05    --   46.62  37.00-180.00  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0361456000
_diffrn_orient_matrix_UB_12      -0.0182040000
_diffrn_orient_matrix_UB_13      -0.0683583000
_diffrn_orient_matrix_UB_21      -0.1430594000
_diffrn_orient_matrix_UB_22      0.1393608000
_diffrn_orient_matrix_UB_23      -0.0127451000
_diffrn_orient_matrix_UB_31      0.2051645000
_diffrn_orient_matrix_UB_32      0.1002278000
_diffrn_orient_matrix_UB_33      0.0053842000
_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                2341
_reflns_number_total             2447
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT n/a (Sheldrick, 2015)'
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.00088(17)
_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   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2447
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0281
_refine_ls_restrained_S_all      1.062
_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)+(0.0362P)²+0.7775P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0761
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C8(H8A,H8B), C6(H6A,H6B), C10(H10A,H10B), C1(H1A,H1B), C9(H9A,
 H9B), C7(H7A,H7B), C2(H2A,H2B)
;
_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
S2 S 0.18847(5) 0.23741(4) 0.26805(2) 0.01432(11) Uani 1 1 d . . . . .
S1 S 0.27191(6) 0.27951(4) 0.42402(2) 0.01996(12) Uani 1 1 d . . . . .
O4 O 0.30888(17) 0.10380(12) 0.25255(5) 0.0218(2) Uani 1 1 d . . . . .
O3 O 0.00014(17) 0.21770(12) 0.30596(5) 0.0204(2) Uani 1 1 d . . . . .
O2 O 0.16426(17) 0.42683(14) 0.42651(5) 0.0269(3) Uani 1 1 d . . . . .
O1 O 0.46739(18) 0.27139(14) 0.47492(5) 0.0270(3) Uani 1 1 d . . . . .
C5 C 0.1021(2) 0.33289(16) 0.20042(6) 0.0143(3) Uani 1 1 d . . . . .
H5 H 0.041160 0.432646 0.211897 0.017 Uiso 1 1 calc R U . . .
C4 C 0.3720(2) 0.36408(16) 0.30546(6) 0.0170(3) Uani 1 1 d . . . . .
H4A H 0.491495 0.390281 0.277884 0.020 Uiso 1 1 calc R U . . .
H4B H 0.292289 0.457360 0.315118 0.020 Uiso 1 1 calc R U . . .
C3 C 0.4706(2) 0.29851(16) 0.36343(6) 0.0159(3) Uani 1 1 d . . . . .
H3 H 0.538476 0.199014 0.354880 0.019 Uiso 1 1 calc R U . . .
C8 C 0.0307(2) 0.33899(18) 0.06834(7) 0.0212(3) Uani 1 1 d . . . . .
H8A H -0.022614 0.390999 0.031209 0.025 Uiso 1 1 calc R U . . .
H8B H 0.089432 0.240228 0.056396 0.025 Uiso 1 1 calc R U . . .
C6 C 0.2940(2) 0.35849(17) 0.15820(6) 0.0173(3) Uani 1 1 d . . . . .
H6A H 0.404374 0.424174 0.178382 0.021 Uiso 1 1 calc R U . . .
H6B H 0.365098 0.261501 0.149342 0.021 Uiso 1 1 calc R U . . .
C10 C -0.0824(2) 0.24071(17) 0.16977(7) 0.0174(3) Uani 1 1 d . . . . .
H10A H -0.028387 0.138632 0.160935 0.021 Uiso 1 1 calc R U . . .
H10B H -0.206998 0.231737 0.197401 0.021 Uiso 1 1 calc R U . . .
C1 C 0.6756(2) 0.34147(18) 0.45706(7) 0.0218(3) Uani 1 1 d . . . . .
H1A H 0.795184 0.266434 0.457917 0.026 Uiso 1 1 calc R U . . .
H1B H 0.715952 0.423529 0.485363 0.026 Uiso 1 1 calc R U . . .
C9 C -0.1595(2) 0.31659(18) 0.11088(7) 0.0207(3) Uani 1 1 d . . . . .
H9A H -0.273679 0.254120 0.090611 0.025 Uiso 1 1 calc R U . . .
H9B H -0.225478 0.414956 0.120253 0.025 Uiso 1 1 calc R U . . .
C7 C 0.2129(2) 0.43118(18) 0.09894(6) 0.0192(3) Uani 1 1 d . . . . .
H7A H 0.157405 0.533058 0.107455 0.023 Uiso 1 1 calc R U . . .
H7B H 0.336934 0.440757 0.071165 0.023 Uiso 1 1 calc R U . . .
C2 C 0.6409(2) 0.40231(17) 0.39364(6) 0.0192(3) Uani 1 1 d . . . . .
H2A H 0.779793 0.400575 0.371398 0.023 Uiso 1 1 calc R U . . .
H2B H 0.585903 0.506589 0.394787 0.023 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
S2 O4 1.4463(11) . ?
S2 O3 1.4493(11) . ?
S2 C5 1.7877(14) . ?
S2 C4 1.7793(14) . ?
S1 O2 1.4714(12) . ?
S1 O1 1.6191(11) . ?
S1 C3 1.8360(14) . ?
O1 C1 1.4779(18) . ?
C5 H5 1.0000 . ?
C5 C6 1.5324(18) . ?
C5 C10 1.5369(19) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C3 1.5182(19) . ?
C3 H3 1.0000 . ?
C3 C2 1.5322(19) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.524(2) . ?
C8 C7 1.5264(19) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.5318(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C9 1.530(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.512(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 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
O4 S2 O3 116.83(6) . . ?
O4 S2 C5 109.61(6) . . ?
O4 S2 C4 108.48(6) . . ?
O3 S2 C5 108.66(6) . . ?
O3 S2 C4 107.87(6) . . ?
C4 S2 C5 104.68(7) . . ?
O2 S1 O1 109.59(6) . . ?
O2 S1 C3 104.36(7) . . ?
O1 S1 C3 91.30(6) . . ?
C1 O1 S1 114.69(9) . . ?
S2 C5 H5 108.4 . . ?
C6 C5 S2 111.51(9) . . ?
C6 C5 H5 108.4 . . ?
C6 C5 C10 111.93(11) . . ?
C10 C5 S2 108.03(10) . . ?
C10 C5 H5 108.4 . . ?
S2 C4 H4A 109.2 . . ?
S2 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C3 C4 S2 112.18(10) . . ?
C3 C4 H4A 109.2 . . ?
C3 C4 H4B 109.2 . . ?
S1 C3 H3 109.9 . . ?
C4 C3 S1 113.34(10) . . ?
C4 C3 H3 109.9 . . ?
C4 C3 C2 112.56(12) . . ?
C2 C3 S1 101.01(9) . . ?
C2 C3 H3 109.9 . . ?
H8A C8 H8B 108.1 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C9 C8 C7 110.74(12) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C5 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C7 C6 C5 110.39(11) . . ?
C7 C6 H6A 109.6 . . ?
C7 C6 H6B 109.6 . . ?
C5 C10 H10A 109.6 . . ?
C5 C10 H10B 109.6 . . ?
H10A C10 H10B 108.2 . . ?
C9 C10 C5 110.06(12) . . ?
C9 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
O1 C1 H1A 110.2 . . ?
O1 C1 H1B 110.2 . . ?
O1 C1 C2 107.38(11) . . ?
H1A C1 H1B 108.5 . . ?
C2 C1 H1A 110.2 . . ?
C2 C1 H1B 110.2 . . ?
C8 C9 C10 111.13(12) . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C8 C7 C6 111.45(12) . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C3 C2 H2A 110.7 . . ?
C3 C2 H2B 110.7 . . ?
C1 C2 C3 105.27(12) . . ?
C1 C2 H2A 110.7 . . ?
C1 C2 H2B 110.7 . . ?
H2A C2 H2B 108.8 . . ?

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
S2 C5 C6 C7 176.33(10) . . . . ?
S2 C5 C10 C9 -179.00(10) . . . . ?
S2 C4 C3 S1 -70.17(12) . . . . ?
S2 C4 C3 C2 175.97(10) . . . . ?
S1 O1 C1 C2 -0.01(16) . . . . ?
S1 C3 C2 C1 44.13(12) . . . . ?
O4 S2 C5 C6 -51.58(11) . . . . ?
O4 S2 C5 C10 71.82(11) . . . . ?
O4 S2 C4 C3 -60.66(11) . . . . ?
O3 S2 C5 C6 179.66(9) . . . . ?
O3 S2 C5 C10 -56.95(11) . . . . ?
O3 S2 C4 C3 66.77(11) . . . . ?
O2 S1 O1 C1 -81.86(12) . . . . ?
O2 S1 C3 C4 -49.41(11) . . . . ?
O2 S1 C3 C2 71.23(10) . . . . ?
O1 S1 C3 C4 -160.02(11) . . . . ?
O1 S1 C3 C2 -39.38(10) . . . . ?
O1 C1 C2 C3 -30.18(15) . . . . ?
C5 S2 C4 C3 -177.63(10) . . . . ?
C5 C6 C7 C8 -55.30(16) . . . . ?
C5 C10 C9 C8 56.63(16) . . . . ?
C4 S2 C5 C6 64.61(11) . . . . ?
C4 S2 C5 C10 -172.00(9) . . . . ?
C4 C3 C2 C1 165.32(12) . . . . ?
C3 S1 O1 C1 23.89(11) . . . . ?
C6 C5 C10 C9 -55.86(16) . . . . ?
C10 C5 C6 C7 55.17(16) . . . . ?
C9 C8 C7 C6 56.70(17) . . . . ?
C7 C8 C9 C10 -57.41(17) . . . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.590
_oxdiff_exptl_absorpt_empirical_full_min 0.680
####################################################################### 
# 
# 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_hpd237
_database_code_depnum_ccdc_archive 'CCDC 2042736'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman'
;University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2020-11-05 deposited with the CCDC.	2022-03-21 downloaded from the CCDC.
;
_audit_creation_date             2020-10-26
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H17 N O2 S'
_chemical_formula_sum            'C15 H17 N O2 S'
_chemical_formula_weight         275.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S'
_chemical_oxdiff_usercomment     'SO2 small vial'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.06120(12)
_cell_length_b                   15.82137(16)
_cell_length_c                   10.26220(14)
_cell_angle_alpha                90
_cell_angle_beta                 114.8370(16)
_cell_angle_gamma                90
_cell_volume                     1335.12(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9829
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.3960
_cell_measurement_theta_min      5.3550
_shelx_estimated_absorpt_T_max   0.825
_shelx_estimated_absorpt_T_min   0.591
_exptl_absorpt_coefficient_mu    2.130
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.342
_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    1.370
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             584
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 -7 -4 0.0556
5 5 -1 0.0687
-4 7 4 0.0371
-6 -3 2 0.0491
3 -3 -6 0.0426
4 6 -5 0.0504
-3 4 6 0.0542
-3 -7 4 0.0578

_exptl_crystal_size_max          0.276
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.094
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4.0455 -6.6785 -3.8738 0.0902 0.6733 0.7339
5.0530 4.9763 -1.4110 0.1126 0.8598 -0.4980
-3.9434 6.8341 3.8595 -0.0879 -0.6558 -0.7498
-5.5518 -3.2654 2.1170 -0.1237 -0.9416 0.3133
2.9894 -3.1181 -6.2945 0.6558 0.4491 0.6069
3.5526 5.6718 -5.1626 0.7938 0.5457 -0.2686
-2.7555 4.0468 6.0918 -0.6027 -0.4124 -0.6832
-3.1903 -7.4830 4.0454 -0.7165 -0.4931 0.4934

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15529
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.259
_diffrn_reflns_theta_min         5.379
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -121.00 -32.00   0.50    0.05    --  -46.87 -31.00 -82.00  178
  2  ω     33.00 122.00   0.50    0.05    --   46.87  31.00  77.00  178
  3  ω    -28.00  38.00   0.50    0.05    --   46.87 -31.00 -82.00  132
  4  ω   -163.00 -73.00   0.50    0.10    --  -88.50 -31.00 -82.00  180
  5  ω     91.00 178.00   0.50    0.10    --  106.69  31.00  77.00  174
  6  ω   -120.00 -87.00   0.50    0.05    --  -46.87-125.00  60.00   66
  7  ω    -38.00  28.00   0.50    0.05    --  -46.87  31.00  77.00  132
  8  ω    -28.00  30.00   0.50    0.05    --   46.87 -19.00-180.00  116
  9  ω    -51.00 -16.00   0.50    0.10    --  -88.50  45.00  60.00   70
 10  ω    -71.00 -15.00   0.50    0.10    --  -88.50  61.00-120.00  112
 11  ω   -160.00-100.00   0.50    0.10    --  -88.50 -94.00  30.00  120
 12  ω    -51.00 -16.00   0.50    0.10    --  -88.50  45.00 150.00   70
 13  ω    -51.00 -16.00   0.50    0.10    --  -88.50  45.00 -90.00   70
 14  ω     34.00  71.00   0.50    0.10    --  106.69 -61.00 -60.00   74
 15  ω     34.00  71.00   0.50    0.10    --  106.69 -61.00  30.00   74
 16  ω     34.00 101.00   0.50    0.10    --  106.69 -77.00-180.00  134
 17  ω     34.00  71.00   0.50    0.10    --  106.69 -61.00-180.00   74
 18  ω     95.00 178.00   0.50    0.10    --  106.69 125.00 -90.00  166
 19  ω     92.00 178.00   0.50    0.10    --  106.69  45.00 150.00  172
 20  ω     34.00 101.00   0.50    0.10    --  106.69 -77.00   0.00  134
 21  ω     34.00 101.00   0.50    0.10    --  106.69 -77.00 -90.00  134
 22  ω     34.00  71.00   0.50    0.10    --  106.69 -61.00   0.00   74
 23  ω   -120.00 -83.00   0.50    0.05    --  -46.87 -57.00  30.00   74
 24  ω     32.00 121.00   0.50    0.05    --   46.87  37.00 150.00  178
 25  ω     32.00 121.00   0.50    0.05    --   46.87  37.00 -30.00  178
 26  ω     32.00 121.00   0.50    0.05    --   46.87  37.00 -90.00  178
 27  ω     32.00 121.00   0.50    0.05    --   46.87  37.00-120.00  178
 28  ω   -161.00-136.00   0.50    0.10    --  -88.50 -45.00-150.00   50
;
_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      -0.0581928000
_diffrn_orient_matrix_UB_12      0.0388819000
_diffrn_orient_matrix_UB_13      -0.1510812000
_diffrn_orient_matrix_UB_21      0.1757291000
_diffrn_orient_matrix_UB_22      -0.0019487000
_diffrn_orient_matrix_UB_23      0.0130808000
_diffrn_orient_matrix_UB_31      -0.0291378000
_diffrn_orient_matrix_UB_32      -0.0892249000
_diffrn_orient_matrix_UB_33      -0.0660528000
_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                2515
_reflns_number_total             2694
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT n/a (Sheldrick, 2015)'
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0009(2)
_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   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2694
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0309
_refine_ls_restrained_S_all      1.076
_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)+(0.0415P)²+0.5688P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0846
_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:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C11(H11A,H11B), C14(H14A,H14B), C13(H13A,H13B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C4(H4), C9(H9), C6(H6), C3(H3), C5(H5)
;
_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 0.31364(4) 0.46193(2) 0.22813(3) 0.01334(12) Uani 1 1 d . . . . .
O1 O 0.24285(12) 0.52552(6) 0.28605(11) 0.0199(2) Uani 1 1 d . . . . .
O2 O 0.26517(12) 0.46216(6) 0.07478(10) 0.0191(2) Uani 1 1 d . . . . .
C10 C 0.53069(15) 0.47016(8) 0.31665(14) 0.0137(3) Uani 1 1 d . . . . .
H10 H 0.566304 0.458612 0.421315 0.016 Uiso 1 1 calc R U . . .
C15 C 0.57423(16) 0.56204(8) 0.29811(14) 0.0168(3) Uani 1 1 d . . . . .
H15A H 0.534446 0.575502 0.194699 0.020 Uiso 1 1 calc R U . . .
H15B H 0.521348 0.601150 0.340740 0.020 Uiso 1 1 calc R U . . .
N1 N 0.37932(13) 0.32724(7) 0.39235(12) 0.0163(2) Uani 1 1 d . . . . .
C7 C 0.07137(16) 0.25022(8) 0.26131(14) 0.0153(3) Uani 1 1 d . . . . .
C11 C 0.61489(15) 0.40720(8) 0.25681(14) 0.0159(3) Uani 1 1 d . . . . .
H11A H 0.576863 0.415952 0.152173 0.019 Uiso 1 1 calc R U . . .
H11B H 0.587344 0.348704 0.272783 0.019 Uiso 1 1 calc R U . . .
C8 C 0.19845(17) 0.21423(8) 0.38360(14) 0.0176(3) Uani 1 1 d . . . . .
H8 H 0.180890 0.163081 0.423489 0.021 Uiso 1 1 calc R U . . .
C2 C 0.10173(15) 0.32723(8) 0.20512(13) 0.0143(3) Uani 1 1 d . . . . .
C14 C 0.75937(16) 0.57320(9) 0.37258(15) 0.0181(3) Uani 1 1 d . . . . .
H14A H 0.787940 0.631699 0.357718 0.022 Uiso 1 1 calc R U . . .
H14B H 0.797380 0.564016 0.477114 0.022 Uiso 1 1 calc R U . . .
C4 C -0.17207(16) 0.32387(9) 0.01880(15) 0.0205(3) Uani 1 1 d . . . . .
H4 H -0.255955 0.348317 -0.063610 0.025 Uiso 1 1 calc R U . . .
C1 C 0.26199(15) 0.36111(8) 0.27974(13) 0.0134(3) Uani 1 1 d . . . . .
C9 C 0.34595(17) 0.25343(9) 0.44361(15) 0.0185(3) Uani 1 1 d . . . . .
H9 H 0.429691 0.228142 0.525139 0.022 Uiso 1 1 calc R U . . .
C13 C 0.84471(16) 0.51090(9) 0.31329(15) 0.0185(3) Uani 1 1 d . . . . .
H13A H 0.812344 0.522395 0.210073 0.022 Uiso 1 1 calc R U . . .
H13B H 0.963958 0.518306 0.364314 0.022 Uiso 1 1 calc R U . . .
C6 C -0.08284(17) 0.21084(9) 0.19267(15) 0.0189(3) Uani 1 1 d . . . . .
H6 H -0.104035 0.159472 0.229648 0.023 Uiso 1 1 calc R U . . .
C3 C -0.02464(16) 0.36411(9) 0.08301(14) 0.0170(3) Uani 1 1 d . . . . .
H3 H -0.007255 0.416337 0.045966 0.020 Uiso 1 1 calc R U . . .
C5 C -0.20104(16) 0.24677(9) 0.07326(15) 0.0204(3) Uani 1 1 d . . . . .
H5 H -0.303514 0.219615 0.026559 0.024 Uiso 1 1 calc R U . . .
C12 C 0.79947(16) 0.42022(9) 0.33246(15) 0.0182(3) Uani 1 1 d . . . . .
H12A H 0.837855 0.407749 0.436084 0.022 Uiso 1 1 calc R U . . .
H12B H 0.854046 0.380571 0.292227 0.022 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 1.4483(10) . ?
S1 O2 1.4453(10) . ?
S1 C10 1.7915(13) . ?
S1 C1 1.8032(13) . ?
C10 H10 1.0000 . ?
C10 C15 1.5388(18) . ?
C10 C11 1.5313(17) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C14 1.5338(17) . ?
N1 C1 1.3118(16) . ?
N1 C9 1.3658(17) . ?
C7 C8 1.4181(19) . ?
C7 C2 1.4234(18) . ?
C7 C6 1.4177(18) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.5335(17) . ?
C8 H8 0.9500 . ?
C8 C9 1.3634(19) . ?
C2 C1 1.4312(18) . ?
C2 C3 1.4200(18) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C13 1.5281(19) . ?
C4 H4 0.9500 . ?
C4 C3 1.3728(19) . ?
C4 C5 1.412(2) . ?
C9 H9 0.9500 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C12 1.5273(19) . ?
C6 H6 0.9500 . ?
C6 C5 1.367(2) . ?
C3 H3 0.9500 . ?
C5 H5 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 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 C10 108.82(6) . . ?
O1 S1 C1 106.24(6) . . ?
O2 S1 O1 117.43(6) . . ?
O2 S1 C10 108.59(6) . . ?
O2 S1 C1 108.93(6) . . ?
C10 S1 C1 106.29(6) . . ?
S1 C10 H10 108.8 . . ?
C15 C10 S1 106.85(9) . . ?
C15 C10 H10 108.8 . . ?
C11 C10 S1 112.03(9) . . ?
C11 C10 H10 108.8 . . ?
C11 C10 C15 111.60(11) . . ?
C10 C15 H15A 109.8 . . ?
C10 C15 H15B 109.8 . . ?
H15A C15 H15B 108.3 . . ?
C14 C15 C10 109.31(11) . . ?
C14 C15 H15A 109.8 . . ?
C14 C15 H15B 109.8 . . ?
C1 N1 C9 117.39(11) . . ?
C8 C7 C2 118.62(12) . . ?
C6 C7 C8 121.85(12) . . ?
C6 C7 C2 119.53(12) . . ?
C10 C11 H11A 109.8 . . ?
C10 C11 H11B 109.8 . . ?
C10 C11 C12 109.31(10) . . ?
H11A C11 H11B 108.3 . . ?
C12 C11 H11A 109.8 . . ?
C12 C11 H11B 109.8 . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.65(12) . . ?
C9 C8 H8 120.2 . . ?
C7 C2 C1 115.42(11) . . ?
C3 C2 C7 119.19(12) . . ?
C3 C2 C1 125.39(12) . . ?
C15 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C13 C14 C15 110.97(11) . . ?
C13 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 121.06(13) . . ?
C5 C4 H4 119.5 . . ?
N1 C1 S1 113.94(9) . . ?
N1 C1 C2 125.66(12) . . ?
C2 C1 S1 120.29(10) . . ?
N1 C9 H9 118.4 . . ?
C8 C9 N1 123.27(12) . . ?
C8 C9 H9 118.4 . . ?
C14 C13 H13A 109.6 . . ?
C14 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C12 C13 C14 110.27(11) . . ?
C12 C13 H13A 109.6 . . ?
C12 C13 H13B 109.6 . . ?
C7 C6 H6 120.0 . . ?
C5 C6 C7 120.01(13) . . ?
C5 C6 H6 120.0 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.64(13) . . ?
C4 C3 H3 120.2 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.54(12) . . ?
C6 C5 H5 119.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C13 C12 C11 110.84(11) . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?

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 C10 C15 C14 179.75(9) . . . . ?
S1 C10 C11 C12 177.55(9) . . . . ?
O1 S1 C10 C15 -55.11(10) . . . . ?
O1 S1 C10 C11 -177.61(9) . . . . ?
O1 S1 C1 N1 -99.42(10) . . . . ?
O1 S1 C1 C2 77.04(11) . . . . ?
O2 S1 C10 C15 73.80(9) . . . . ?
O2 S1 C10 C11 -48.70(10) . . . . ?
O2 S1 C1 N1 133.20(10) . . . . ?
O2 S1 C1 C2 -50.35(12) . . . . ?
C10 S1 C1 N1 16.37(11) . . . . ?
C10 S1 C1 C2 -167.17(10) . . . . ?
C10 C15 C14 C13 57.03(14) . . . . ?
C10 C11 C12 C13 -57.72(14) . . . . ?
C15 C10 C11 C12 57.78(14) . . . . ?
C15 C14 C13 C12 -57.97(14) . . . . ?
C7 C8 C9 N1 0.4(2) . . . . ?
C7 C2 C1 S1 -175.80(9) . . . . ?
C7 C2 C1 N1 0.22(19) . . . . ?
C7 C2 C3 C4 -1.85(19) . . . . ?
C7 C6 C5 C4 -1.2(2) . . . . ?
C11 C10 C15 C14 -57.47(14) . . . . ?
C8 C7 C2 C1 0.18(17) . . . . ?
C8 C7 C2 C3 -179.78(12) . . . . ?
C8 C7 C6 C5 -178.68(12) . . . . ?
C2 C7 C8 C9 -0.45(19) . . . . ?
C2 C7 C6 C5 0.1(2) . . . . ?
C14 C13 C12 C11 58.22(14) . . . . ?
C1 S1 C10 C15 -169.14(8) . . . . ?
C1 S1 C10 C11 68.35(10) . . . . ?
C1 N1 C9 C8 0.0(2) . . . . ?
C1 C2 C3 C4 178.20(12) . . . . ?
C9 N1 C1 S1 175.91(9) . . . . ?
C9 N1 C1 C2 -0.3(2) . . . . ?
C6 C7 C8 C9 178.33(13) . . . . ?
C6 C7 C2 C1 -178.63(11) . . . . ?
C6 C7 C2 C3 1.41(19) . . . . ?
C3 C2 C1 S1 4.16(18) . . . . ?
C3 C2 C1 N1 -179.83(12) . . . . ?
C3 C4 C5 C6 0.7(2) . . . . ?
C5 C4 C3 C2 0.8(2) . . . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.394
_oxdiff_exptl_absorpt_empirical_full_min 0.737
####################################################################### 
# 
# 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_hpd144
_database_code_depnum_ccdc_archive 'CCDC 2042731'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman'
;University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2020-11-05 deposited with the CCDC.	2022-03-21 downloaded from the CCDC.
;
_audit_creation_date             2020-07-03
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C12.5 H15 O4 S0.5)'
_chemical_formula_sum            'C25 H30 O8 S'
_chemical_formula_weight         490.55
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S'
_chemical_oxdiff_usercomment     VNy138-14
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'
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.04584(4)
_cell_length_b                   19.87397(12)
_cell_length_c                   12.32816(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.9688(4)
_cell_angle_gamma                90
_cell_volume                     2447.98(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    43038
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.6100
_cell_measurement_theta_min      3.6070
_shelx_estimated_absorpt_T_max   0.885
_shelx_estimated_absorpt_T_min   0.776
_exptl_absorpt_coefficient_mu    1.580
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.555
_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    1.331
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1040
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 13 0 0.0674
3 -2 -7 0.0652
-3 1 7 0.0570
0 12 3 0.0852
6 -1 3 0.0525
1 -12 -2 0.0561
-6 0 -3 0.0206

_exptl_crystal_size_max          0.169
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.079
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.2511 12.8934 -0.1254 0.0814 0.3314 0.9400
2.8078 -2.1157 -7.4202 0.2060 0.8602 -0.4666
-2.8465 1.2004 7.4835 -0.2134 -0.8904 0.4021
0.2023 12.0145 2.8688 0.1576 -0.0397 0.9867
5.8913 -1.3305 2.5591 0.9692 -0.2329 -0.0801
0.9009 -12.2391 -2.3839 0.0241 -0.0039 -0.9997
-5.8558 0.4603 -2.7425 -0.9723 0.2337 0.0089

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            71221
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.528
_diffrn_reflns_theta_min         3.605
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -123.00 -32.00   0.50    0.05    --  -46.87 -24.00 179.00  182
  2  ω    -33.00  29.00   0.50    0.05    --  -46.87  24.00 -16.00  124
  3  ω     33.00 123.00   0.50    0.05    --   46.87  24.00 -16.00  180
  4  ω    -28.00  33.00   0.50    0.05    --   46.87 -24.00 179.00  122
  5  ω   -164.00 -74.00   0.50    0.15    --  -88.50 -24.00 179.00  180
  6  ω     92.00 178.00   0.50    0.15    --  106.69  24.00 -16.00  172
  7  ω    -30.00  29.00   0.50    0.05    --  -46.87  19.00 120.00  118
  8  ω   -120.00 -87.00   0.50    0.05    --  -46.87-125.00 -90.00   66
  9  ω   -120.00 -87.00   0.50    0.05    --  -46.87-125.00  30.00   66
 10  ω     31.00 120.00   0.50    0.05    --   46.87  55.00 162.28  178
 11  ω     32.00 120.00   0.50    0.05    --   46.87  54.00 120.31  176
 12  ω     32.00 120.00   0.50    0.05    --   46.87  52.00 136.78  176
 13  ω     31.00 120.00   0.50    0.05    --   46.87  55.00  74.74  178
 14  ω     32.00 120.00   0.50    0.05    --   46.87  52.00 112.72  176
 15  ω     32.00 121.00   0.50    0.05    --   46.87  37.00  30.00  178
 16  ω   -101.00 -15.00   0.50    0.15    --  -88.50  77.00 120.00  172
 17  ω   -160.00 -73.00   0.50    0.15    --  -88.50 -55.00  91.08  174
 18  ω   -160.00 -73.00   0.50    0.15    --  -88.50 -53.00  64.69  174
 19  ω   -160.00 -73.00   0.50    0.15    --  -88.50 -50.00 104.73  174
 20  ω   -160.00 -72.00   0.50    0.15    --  -88.50 -54.00  58.93  176
 21  ω   -160.00 -72.00   0.50    0.15    --  -88.50 -54.00  54.72  176
 22  ω   -160.00 -73.00   0.50    0.15    --  -88.50 -52.00 114.17  174
 23  ω   -160.00 -73.00   0.50    0.15    --  -88.50 -55.00  12.72  174
 24  ω   -160.00 -73.00   0.50    0.15    --  -88.50 -55.00 100.02  174
 25  ω   -160.00 -73.00   0.50    0.15    --  -88.50 -52.00  -1.56  174
 26  ω    -51.00 -16.00   0.50    0.15    --  -88.50  45.00-180.00   70
 27  ω   -161.00 -74.00   0.50    0.15    --  -88.50 -45.00  30.00  174
 28  ω   -160.00 -78.00   0.50    0.15    --  -88.50 -56.00  -4.20  164
 29  ω   -160.00 -73.00   0.50    0.15    --  -88.50 -55.00  87.26  174
 30  ω   -160.00 -72.00   0.50    0.15    --  -88.50 -54.00 108.05  176
 31  ω   -160.00 -73.00   0.50    0.15    --  -88.50 -55.00  23.91  174
 32  ω   -160.00 -73.00   0.50    0.15    --  -88.50 -55.00 131.52  174
 33  ω   -160.00 -73.00   0.50    0.15    --  -88.50 -55.00 124.56  174
 34  ω   -160.00 -73.00   0.50    0.15    --  -88.50 -55.00  75.07  174
 35  ω   -160.00 -78.00   0.50    0.15    --  -88.50 -56.00  50.90  164
 36  ω   -160.00 -73.00   0.50    0.15    --  -88.50 -55.00  84.57  174
 37  ω    -71.00 -15.00   0.50    0.15    --  -88.50  61.00 120.00  112
 38  ω   -160.00 -72.00   0.50    0.15    --  -88.50 -54.00   3.66  176
 39  ω   -160.00 -73.00   0.50    0.15    --  -88.50 -55.00  33.78  174
 40  ω   -160.00 -73.00   0.50    0.15    --  -88.50 -52.00  23.72  174
 41  ω    -71.00 -15.00   0.50    0.15    --  -88.50  61.00  90.00  112
 42  ω     91.00 178.00   0.50    0.15    --  106.69  61.00 150.00  174
 43  ω     34.00  89.00   0.50    0.15    --  106.69 -77.00 150.00  110
 44  ω    128.00 175.00   0.50    0.15    --  106.69  61.00  30.00   94
 45  ω     92.00 121.00   0.50    0.15    --  106.69  61.00  30.00   58
 46  ω     90.00 160.00   0.50    0.15    --  106.69  54.00 170.45  140
 47  ω     71.00  97.00   0.50    0.15    --  106.69 -77.00-120.00   52
 48  ω     39.00  67.00   0.50    0.15    --  106.69 -77.00-120.00   56
 49  ω     34.00  59.00   0.50    0.15    --  106.69 -61.00-150.00   50
 50  ω     37.00  68.00   0.50    0.15    --  106.69 -61.00-120.00   62
 51  ω     97.00 174.00   0.50    0.15    --  106.69  55.00  80.25  154
 52  ω     34.00 100.00   0.50    0.15    --  106.69 -77.00  60.00  132
 53  ω     34.00  70.00   0.50    0.15    --  106.69 -61.00-180.00   72
 54  ω     58.00 101.00   0.50    0.15    --  106.69-125.00  60.00   86
 55  ω     35.00  68.00   0.50    0.15    --  106.69 -61.00 -90.00   66
;
_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      0.1527324000
_diffrn_orient_matrix_UB_12      0.0036199000
_diffrn_orient_matrix_UB_13      0.0290046000
_diffrn_orient_matrix_UB_21      0.0165796000
_diffrn_orient_matrix_UB_22      0.0242470000
_diffrn_orient_matrix_UB_23      -0.1165627000
_diffrn_orient_matrix_UB_31      -0.0130610000
_diffrn_orient_matrix_UB_32      0.0735175000
_diffrn_orient_matrix_UB_33      0.0369743000
_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         0.853
_reflns_Friedel_fraction_full    0.955
_reflns_Friedel_fraction_max     0.873
_reflns_number_gt                9233
_reflns_number_total             9458
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT n/a (Sheldrick, 2015)'
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 4120 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.020(6)
_refine_ls_extinction_coef       0.00075(14)
_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   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     620
_refine_ls_number_reflns         9458
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0293
_refine_ls_restrained_S_all      1.045
_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)+(0.0498P)²+0.3934P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0779
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C26(H26), C33(H33), C39(H39), C37(H37), C1(H1), C14(H14), C8(H8), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C40(H40A,H40B), C31(H31A,H31B), C43(H43A,H43B), C32(H32A,H32B), C28(H28A,
 H28B), C3(H3A,H3B), C15(H15A,H15B), C7(H7A,H7B), C6(H6A,H6B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C35(H35), C41(H41), C36(H36), C10(H10), C11(H11), C16(H16)
2.d X=CH2 refined with riding coordinates:
 C44(H44A,H44B), C42(H42A,H42B), C19(H19A,H19B), C17(H17A,H17B)
2.e Idealised Me refined as rotating group:
 C50(H50A,H50B,H50C), C49(H49A,H49B,H49C), C46(H46A,H46B,H46C), C25(H25A,H25B,
 H25C), C21(H21A,H21B,H21C), C24(H24A,H24B,H24C)
;
_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
S2 S 0.82246(5) 0.36934(3) 0.24239(4) 0.02183(12) Uani 1 1 d . . . . .
O14 O 1.31761(17) 0.23631(11) 0.24082(14) 0.0341(4) Uani 1 1 d . . . . .
O13 O 1.14131(15) 0.19633(9) 0.31805(12) 0.0238(3) Uani 1 1 d . . . . .
O15 O 1.21432(16) 0.37578(9) 0.51273(13) 0.0269(3) Uani 1 1 d . . . . .
O10 O 0.90231(17) 0.42731(9) 0.27561(14) 0.0305(4) Uani 1 1 d . . . . .
O9 O 0.72210(17) 0.34816(9) 0.31079(13) 0.0278(4) Uani 1 1 d . . . . .
C47 C 1.2250(2) 0.24628(13) 0.29333(17) 0.0253(5) Uani 1 1 d . . . . .
O16 O 1.42840(17) 0.40940(10) 0.50913(17) 0.0365(4) Uani 1 1 d . . . . .
C40 C 0.7436(2) 0.38613(13) 0.10845(18) 0.0251(5) Uani 1 1 d . . . . .
H40A H 0.812436 0.390665 0.056945 0.030 Uiso 1 1 calc R U . . .
H40B H 0.684011 0.348253 0.083766 0.030 Uiso 1 1 calc R U . . .
C30 C 0.8681(2) 0.12065(12) 0.13470(17) 0.0239(5) Uani 1 1 d . . . . .
O11 O 0.89455(17) 0.07146(9) 0.05214(13) 0.0260(3) Uani 1 1 d . . . . .
C35 C 1.0808(2) 0.22079(12) 0.49643(18) 0.0233(5) Uani 1 1 d . . . . .
H35 H 1.040298 0.190630 0.543003 0.028 Uiso 1 1 calc R U . . .
C27 C 0.8744(2) 0.22833(12) 0.21558(17) 0.0207(4) Uani 1 1 d . . . . .
C31 C 0.9155(2) 0.08424(13) 0.24144(18) 0.0249(5) Uani 1 1 d . . . . .
H31A H 0.876476 0.038480 0.240228 0.030 Uiso 1 1 calc R U . . .
H31B H 1.014202 0.079723 0.248136 0.030 Uiso 1 1 calc R U . . .
C34 C 1.0336(2) 0.22619(12) 0.37650(17) 0.0210(4) Uani 1 1 d . . . . .
C50 C 1.2243(3) 0.37369(16) 0.2792(2) 0.0332(6) Uani 1 1 d . . . . .
H50A H 1.188858 0.370474 0.202256 0.050 Uiso 1 1 calc R U . . .
H50B H 1.322291 0.375285 0.284953 0.050 Uiso 1 1 calc R U . . .
H50C H 1.190308 0.414674 0.310880 0.050 Uiso 1 1 calc R U . . .
O12 O 0.82299(17) 0.13861(9) -0.08941(13) 0.0279(4) Uani 1 1 d . . . . .
C26 C 0.9368(2) 0.30030(12) 0.22992(17) 0.0212(4) Uani 1 1 d . . . . .
H26 H 0.992066 0.309625 0.168676 0.025 Uiso 1 1 calc R U . . .
C29 C 0.7228(2) 0.14331(13) 0.13464(18) 0.0252(5) Uani 1 1 d . . . . .
C45 C 0.8739(2) 0.08692(13) -0.05464(18) 0.0248(5) Uani 1 1 d . . . . .
C38 C 1.1800(2) 0.31251(13) 0.34059(19) 0.0252(5) Uani 1 1 d . . . . .
C33 C 0.8986(2) 0.19845(12) 0.33245(17) 0.0221(4) Uani 1 1 d . . . . .
H33 H 0.831709 0.220444 0.375580 0.027 Uiso 1 1 calc R U . . .
C43 C 0.9439(2) 0.18704(12) 0.13083(17) 0.0225(4) Uani 1 1 d . . . . .
H43A H 0.931066 0.207775 0.057474 0.027 Uiso 1 1 calc R U . . .
H43B H 1.040725 0.181313 0.153272 0.027 Uiso 1 1 calc R U . . .
C44 C 0.6156(3) 0.10496(15) 0.1141(2) 0.0332(6) Uani 1 1 d . . . . .
H44A H 0.529165 0.123000 0.120245 0.040 Uiso 1 1 calc R U . . .
H44B H 0.625068 0.059353 0.093077 0.040 Uiso 1 1 calc R U . . .
C41 C 0.6641(3) 0.44969(15) 0.1095(2) 0.0332(6) Uani 1 1 d . . . . .
H41 H 0.710637 0.490908 0.123314 0.040 Uiso 1 1 calc R U . . .
C32 C 0.8740(2) 0.12290(13) 0.33963(18) 0.0241(5) Uani 1 1 d . . . . .
H32A H 0.777628 0.115013 0.345259 0.029 Uiso 1 1 calc R U . . .
H32B H 0.924535 0.105215 0.406823 0.029 Uiso 1 1 calc R U . . .
C39 C 1.0297(2) 0.29928(12) 0.34057(18) 0.0218(4) Uani 1 1 d . . . . .
H39 H 0.991467 0.328186 0.396027 0.026 Uiso 1 1 calc R U . . .
C42 C 0.5340(3) 0.4512(2) 0.0923(3) 0.0519(9) Uani 1 1 d . . . . .
H42A H 0.485194 0.410675 0.078280 0.062 Uiso 1 1 calc R U . . .
H42B H 0.487952 0.492913 0.093797 0.062 Uiso 1 1 calc R U . . .
C49 C 1.2802(4) 0.47213(16) 0.6120(3) 0.0471(7) Uani 1 1 d . . . . .
H49A H 1.220300 0.503473 0.569341 0.071 Uiso 1 1 calc R U . . .
H49B H 1.360256 0.496210 0.643233 0.071 Uiso 1 1 calc R U . . .
H49C H 1.233822 0.452877 0.670875 0.071 Uiso 1 1 calc R U . . .
C28 C 0.7263(2) 0.21683(12) 0.16895(18) 0.0249(5) Uani 1 1 d . . . . .
H28A H 0.664835 0.225205 0.225269 0.030 Uiso 1 1 calc R U . . .
H28B H 0.701213 0.246592 0.105718 0.030 Uiso 1 1 calc R U . . .
C37 C 1.2409(2) 0.31213(13) 0.46240(19) 0.0247(5) Uani 1 1 d . . . . .
H37 H 1.339856 0.305142 0.465871 0.030 Uiso 1 1 calc R U . . .
C36 C 1.1816(2) 0.26032(13) 0.53335(19) 0.0270(5) Uani 1 1 d . . . . .
H36 H 1.218029 0.255971 0.607262 0.032 Uiso 1 1 calc R U . . .
C46 C 0.9221(3) 0.03110(14) -0.1228(2) 0.0348(6) Uani 1 1 d . . . . .
H46A H 0.861716 -0.007545 -0.121407 0.052 Uiso 1 1 calc R U . . .
H46B H 1.012601 0.017743 -0.093279 0.052 Uiso 1 1 calc R U . . .
H46C H 0.923447 0.046685 -0.198062 0.052 Uiso 1 1 calc R U . . .
S1 S 0.46622(5) 0.25322(3) 0.84369(4) 0.02188(12) Uani 1 1 d . . . . .
O3 O 1.03589(15) 0.37361(9) 0.81141(12) 0.0247(3) Uani 1 1 d . . . . .
O2 O 0.50701(16) 0.27615(10) 0.95324(12) 0.0279(4) Uani 1 1 d . . . . .
O5 O 0.77832(15) 0.20903(8) 0.58897(12) 0.0230(3) Uani 1 1 d . . . . .
O7 O 0.39802(17) 0.10170(9) 0.53876(15) 0.0313(4) Uani 1 1 d . . . . .
C10 C 0.5834(2) 0.23598(13) 0.46703(18) 0.0258(5) Uani 1 1 d . . . . .
H10 H 0.579876 0.271972 0.416107 0.031 Uiso 1 1 calc R U . . .
O1 O 0.37850(15) 0.29561(9) 0.77294(13) 0.0264(4) Uani 1 1 d . . . . .
C9 C 0.6478(2) 0.24481(12) 0.58264(17) 0.0219(5) Uani 1 1 d . . . . .
C1 C 0.6117(2) 0.23549(12) 0.77589(17) 0.0207(4) Uani 1 1 d . . . . .
H1 H 0.670868 0.203181 0.820525 0.025 Uiso 1 1 calc R U . . .
O4 O 1.00886(16) 0.34888(9) 0.98698(13) 0.0284(4) Uani 1 1 d . . . . .
O8 O 0.3740(2) 0.04208(12) 0.38283(19) 0.0498(5) Uani 1 1 d . . . . .
C3 C 0.6670(2) 0.36784(13) 0.81730(17) 0.0230(4) Uani 1 1 d . . . . .
H3A H 0.590757 0.392993 0.779390 0.028 Uiso 1 1 calc R U . . .
H3B H 0.647993 0.358579 0.893079 0.028 Uiso 1 1 calc R U . . .
C13 C 0.6102(2) 0.13313(12) 0.63205(18) 0.0234(5) Uani 1 1 d . . . . .
C14 C 0.5695(2) 0.20463(12) 0.66144(17) 0.0217(4) Uani 1 1 d . . . . .
H14 H 0.471155 0.210915 0.641787 0.026 Uiso 1 1 calc R U . . .
C2 C 0.6918(2) 0.30150(12) 0.75631(17) 0.0201(4) Uani 1 1 d . . . . .
C15 C 0.3859(2) 0.17360(14) 0.8563(2) 0.0297(5) Uani 1 1 d . . . . .
H15A H 0.359548 0.154375 0.783139 0.036 Uiso 1 1 calc R U . . .
H15B H 0.448100 0.141825 0.897434 0.036 Uiso 1 1 calc R U . . .
C8 C 0.6626(2) 0.31389(12) 0.63211(17) 0.0219(5) Uani 1 1 d . . . . .
H8 H 0.570833 0.333958 0.622096 0.026 Uiso 1 1 calc R U . . .
C5 C 0.8968(2) 0.36057(12) 0.77012(17) 0.0227(5) Uani 1 1 d . . . . .
C7 C 0.7544(2) 0.36675(13) 0.58780(18) 0.0250(5) Uani 1 1 d . . . . .
H7A H 0.713383 0.411697 0.593919 0.030 Uiso 1 1 calc R U . . .
H7B H 0.759773 0.357775 0.509382 0.030 Uiso 1 1 calc R U . . .
C25 C 0.5959(2) 0.07519(13) 0.7107(2) 0.0288(5) Uani 1 1 d . . . . .
H25A H 0.642375 0.086400 0.782217 0.043 Uiso 1 1 calc R U . . .
H25B H 0.635157 0.034399 0.682665 0.043 Uiso 1 1 calc R U . . .
H25C H 0.500812 0.067440 0.717745 0.043 Uiso 1 1 calc R U . . .
C20 C 1.0772(2) 0.36833(13) 0.91828(18) 0.0241(5) Uani 1 1 d . . . . .
C6 C 0.8972(2) 0.36843(13) 0.64642(17) 0.0244(4) Uani 1 1 d . . . . .
H6A H 0.950503 0.331641 0.618269 0.029 Uiso 1 1 calc R U . . .
H6B H 0.940236 0.411646 0.630582 0.029 Uiso 1 1 calc R U . . .
C18 C 0.8429(2) 0.29068(12) 0.79213(17) 0.0208(4) Uani 1 1 d . . . . .
H18A H 0.859343 0.278460 0.870223 0.025 Uiso 1 1 calc R U . . .
H18B H 0.881841 0.255843 0.747485 0.025 Uiso 1 1 calc R U . . .
C21 C 1.2196(2) 0.39085(15) 0.9404(2) 0.0311(5) Uani 1 1 d . . . . .
H21A H 1.270532 0.375333 0.881569 0.047 Uiso 1 1 calc R U . . .
H21B H 1.258764 0.371864 1.009912 0.047 Uiso 1 1 calc R U . . .
H21C H 1.222843 0.440079 0.944334 0.047 Uiso 1 1 calc R U . . .
C23 C 0.3295(3) 0.06015(14) 0.4649(3) 0.0387(7) Uani 1 1 d . . . . .
C24 C 0.1979(3) 0.04050(17) 0.5016(3) 0.0507(8) Uani 1 1 d . . . . .
H24A H 0.211045 0.003211 0.553613 0.076 Uiso 1 1 calc R U . . .
H24B H 0.137045 0.026345 0.438423 0.076 Uiso 1 1 calc R U . . .
H24C H 0.159349 0.079034 0.536799 0.076 Uiso 1 1 calc R U . . .
C19 C 0.8192(3) 0.46954(14) 0.8497(2) 0.0295(5) Uani 1 1 d . . . . .
H19A H 0.750399 0.494506 0.878688 0.035 Uiso 1 1 calc R U . . .
H19B H 0.904374 0.489442 0.845092 0.035 Uiso 1 1 calc R U . . .
O6 O 0.84493(16) 0.10262(10) 0.61522(13) 0.0289(4) Uani 1 1 d . . . . .
C12 C 0.5339(2) 0.11790(14) 0.51813(19) 0.0284(5) Uani 1 1 d . . . . .
H12 H 0.575167 0.077819 0.485733 0.034 Uiso 1 1 calc R U . . .
C11 C 0.5318(2) 0.17584(14) 0.43918(19) 0.0287(5) Uani 1 1 d . . . . .
H11 H 0.491990 0.169266 0.366621 0.034 Uiso 1 1 calc R U . . .
C22 C 0.7575(2) 0.14354(13) 0.61240(17) 0.0238(5) Uani 1 1 d . . . . .
C16 C 0.2647(3) 0.18414(16) 0.9153(2) 0.0381(6) Uani 1 1 d . . . . .
H16 H 0.277021 0.191887 0.991717 0.046 Uiso 1 1 calc R U . . .
C17 C 0.1425(3) 0.1832(2) 0.8667(3) 0.0541(9) Uani 1 1 d . . . . .
H17A H 0.127503 0.175571 0.790340 0.065 Uiso 1 1 calc R U . . .
H17B H 0.068746 0.190186 0.907802 0.065 Uiso 1 1 calc R U . . .
C4 C 0.7963(2) 0.40708(12) 0.81583(17) 0.0225(5) Uani 1 1 d . . . . .
C48 C 1.3199(2) 0.41705(14) 0.5397(2) 0.0287(5) Uani 1 1 d . . . . .


_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 O10 1.4388(19) . ?
S2 O9 1.4427(18) . ?
S2 C40 1.787(2) . ?
S2 C26 1.806(2) . ?
O14 C47 1.204(3) . ?
O13 C47 1.356(3) . ?
O13 C34 1.485(3) . ?
O15 C37 1.446(3) . ?
O15 C48 1.355(3) . ?
C47 C38 1.527(4) . ?
O16 C48 1.199(3) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C40 C41 1.496(4) . ?
C30 O11 1.455(3) . ?
C30 C31 1.534(3) . ?
C30 C29 1.528(3) . ?
C30 C43 1.526(3) . ?
O11 C45 1.347(3) . ?
C35 H35 0.9500 . ?
C35 C34 1.509(3) . ?
C35 C36 1.324(3) . ?
C27 C26 1.564(3) . ?
C27 C33 1.554(3) . ?
C27 C43 1.550(3) . ?
C27 C28 1.556(3) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.528(3) . ?
C34 C33 1.511(3) . ?
C34 C39 1.518(3) . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
C50 C38 1.523(4) . ?
O12 C45 1.206(3) . ?
C26 H26 1.0000 . ?
C26 C39 1.571(3) . ?
C29 C44 1.322(4) . ?
C29 C28 1.520(3) . ?
C45 C46 1.502(3) . ?
C38 C39 1.532(3) . ?
C38 C37 1.562(3) . ?
C33 H33 1.0000 . ?
C33 C32 1.526(3) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 H44A 0.9500 . ?
C44 H44B 0.9500 . ?
C41 H41 0.9500 . ?
C41 C42 1.302(4) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C39 H39 1.0000 . ?
C42 H42A 0.9500 . ?
C42 H42B 0.9500 . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C49 C48 1.492(4) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C37 H37 1.0000 . ?
C37 C36 1.513(3) . ?
C36 H36 0.9500 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
S1 O2 1.4438(16) . ?
S1 O1 1.4448(17) . ?
S1 C1 1.793(2) . ?
S1 C15 1.790(3) . ?
O3 C5 1.460(2) . ?
O3 C20 1.344(3) . ?
O5 C9 1.487(3) . ?
O5 C22 1.354(3) . ?
O7 C23 1.362(3) . ?
O7 C12 1.451(3) . ?
C10 H10 0.9500 . ?
C10 C9 1.513(3) . ?
C10 C11 1.334(4) . ?
C9 C14 1.536(3) . ?
C9 C8 1.503(3) . ?
C1 H1 1.0000 . ?
C1 C14 1.556(3) . ?
C1 C2 1.571(3) . ?
O4 C20 1.208(3) . ?
O8 C23 1.202(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C2 1.551(3) . ?
C3 C4 1.517(3) . ?
C13 C14 1.533(3) . ?
C13 C25 1.522(3) . ?
C13 C12 1.558(3) . ?
C13 C22 1.538(3) . ?
C14 H14 1.0000 . ?
C2 C8 1.548(3) . ?
C2 C18 1.551(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.497(3) . ?
C8 H8 1.0000 . ?
C8 C7 1.536(3) . ?
C5 C6 1.533(3) . ?
C5 C18 1.525(3) . ?
C5 C4 1.520(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C6 1.538(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C20 C21 1.497(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C23 C24 1.493(5) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C19 H19A 0.9500 . ?
C19 H19B 0.9500 . ?
C19 C4 1.322(4) . ?
O6 C22 1.195(3) . ?
C12 H12 1.0000 . ?
C12 C11 1.506(4) . ?
C11 H11 0.9500 . ?
C16 H16 0.9500 . ?
C16 C17 1.309(4) . ?
C17 H17A 0.9500 . ?
C17 H17B 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
O10 S2 O9 118.04(11) . . ?
O10 S2 C40 107.09(11) . . ?
O10 S2 C26 106.97(10) . . ?
O9 S2 C40 108.98(11) . . ?
O9 S2 C26 108.50(10) . . ?
C40 S2 C26 106.72(10) . . ?
C47 O13 C34 108.46(17) . . ?
C48 O15 C37 117.39(18) . . ?
O14 C47 O13 122.2(2) . . ?
O14 C47 C38 128.5(2) . . ?
O13 C47 C38 109.29(18) . . ?
S2 C40 H40A 109.7 . . ?
S2 C40 H40B 109.7 . . ?
H40A C40 H40B 108.2 . . ?
C41 C40 S2 109.62(16) . . ?
C41 C40 H40A 109.7 . . ?
C41 C40 H40B 109.7 . . ?
O11 C30 C31 102.72(18) . . ?
O11 C30 C29 116.19(18) . . ?
O11 C30 C43 115.53(18) . . ?
C29 C30 C31 110.55(18) . . ?
C43 C30 C31 108.86(18) . . ?
C43 C30 C29 102.98(19) . . ?
C45 O11 C30 120.64(19) . . ?
C34 C35 H35 121.8 . . ?
C36 C35 H35 121.8 . . ?
C36 C35 C34 116.5(2) . . ?
C33 C27 C26 102.85(17) . . ?
C33 C27 C28 109.75(18) . . ?
C43 C27 C26 110.94(17) . . ?
C43 C27 C33 112.63(18) . . ?
C43 C27 C28 98.83(17) . . ?
C28 C27 C26 122.18(19) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 108.1 . . ?
C32 C31 C30 110.9(2) . . ?
C32 C31 H31A 109.5 . . ?
C32 C31 H31B 109.5 . . ?
O13 C34 C35 106.05(16) . . ?
O13 C34 C33 110.60(17) . . ?
O13 C34 C39 103.79(17) . . ?
C35 C34 C33 120.33(19) . . ?
C35 C34 C39 110.48(19) . . ?
C33 C34 C39 104.46(18) . . ?
H50A C50 H50B 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C38 C50 H50A 109.5 . . ?
C38 C50 H50B 109.5 . . ?
C38 C50 H50C 109.5 . . ?
S2 C26 H26 109.4 . . ?
C27 C26 S2 116.98(14) . . ?
C27 C26 H26 109.4 . . ?
C27 C26 C39 106.33(18) . . ?
C39 C26 S2 105.17(15) . . ?
C39 C26 H26 109.4 . . ?
C44 C29 C30 126.1(2) . . ?
C44 C29 C28 127.0(2) . . ?
C28 C29 C30 106.78(19) . . ?
O11 C45 C46 110.6(2) . . ?
O12 C45 O11 123.9(2) . . ?
O12 C45 C46 125.4(2) . . ?
C47 C38 C39 100.53(19) . . ?
C47 C38 C37 105.11(19) . . ?
C50 C38 C47 112.6(2) . . ?
C50 C38 C39 118.4(2) . . ?
C50 C38 C37 112.1(2) . . ?
C39 C38 C37 106.69(18) . . ?
C27 C33 H33 106.1 . . ?
C34 C33 C27 103.99(18) . . ?
C34 C33 H33 106.1 . . ?
C34 C33 C32 118.9(2) . . ?
C32 C33 C27 114.78(19) . . ?
C32 C33 H33 106.1 . . ?
C30 C43 C27 100.13(17) . . ?
C30 C43 H43A 111.7 . . ?
C30 C43 H43B 111.7 . . ?
C27 C43 H43A 111.7 . . ?
C27 C43 H43B 111.7 . . ?
H43A C43 H43B 109.5 . . ?
C29 C44 H44A 120.0 . . ?
C29 C44 H44B 120.0 . . ?
H44A C44 H44B 120.0 . . ?
C40 C41 H41 118.4 . . ?
C42 C41 C40 123.1(3) . . ?
C42 C41 H41 118.4 . . ?
C31 C32 H32A 109.0 . . ?
C31 C32 H32B 109.0 . . ?
C33 C32 C31 112.92(19) . . ?
C33 C32 H32A 109.0 . . ?
C33 C32 H32B 109.0 . . ?
H32A C32 H32B 107.8 . . ?
C34 C39 C26 105.09(18) . . ?
C34 C39 C38 99.75(18) . . ?
C34 C39 H39 110.5 . . ?
C26 C39 H39 110.5 . . ?
C38 C39 C26 119.64(19) . . ?
C38 C39 H39 110.5 . . ?
C41 C42 H42A 120.0 . . ?
C41 C42 H42B 120.0 . . ?
H42A C42 H42B 120.0 . . ?
H49A C49 H49B 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C48 C49 H49A 109.5 . . ?
C48 C49 H49B 109.5 . . ?
C48 C49 H49C 109.5 . . ?
C27 C28 H28A 111.0 . . ?
C27 C28 H28B 111.0 . . ?
C29 C28 C27 103.74(18) . . ?
C29 C28 H28A 111.0 . . ?
C29 C28 H28B 111.0 . . ?
H28A C28 H28B 109.0 . . ?
O15 C37 C38 109.69(19) . . ?
O15 C37 H37 109.3 . . ?
O15 C37 C36 104.22(18) . . ?
C38 C37 H37 109.3 . . ?
C36 C37 C38 114.86(19) . . ?
C36 C37 H37 109.3 . . ?
C35 C36 C37 122.6(2) . . ?
C35 C36 H36 118.7 . . ?
C37 C36 H36 118.7 . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
O2 S1 O1 118.46(11) . . ?
O2 S1 C1 109.41(10) . . ?
O2 S1 C15 106.53(11) . . ?
O1 S1 C1 107.99(10) . . ?
O1 S1 C15 108.41(11) . . ?
C15 S1 C1 105.27(11) . . ?
C20 O3 C5 120.97(17) . . ?
C22 O5 C9 108.41(17) . . ?
C23 O7 C12 115.9(2) . . ?
C9 C10 H10 121.2 . . ?
C11 C10 H10 121.2 . . ?
C11 C10 C9 117.6(2) . . ?
O5 C9 C10 106.40(17) . . ?
O5 C9 C14 103.01(17) . . ?
O5 C9 C8 111.47(17) . . ?
C10 C9 C14 109.79(18) . . ?
C8 C9 C10 120.2(2) . . ?
C8 C9 C14 104.70(17) . . ?
S1 C1 H1 109.7 . . ?
C14 C1 S1 109.96(14) . . ?
C14 C1 H1 109.7 . . ?
C14 C1 C2 106.59(17) . . ?
C2 C1 S1 111.29(15) . . ?
C2 C1 H1 109.7 . . ?
H3A C3 H3B 108.9 . . ?
C2 C3 H3A 110.9 . . ?
C2 C3 H3B 110.9 . . ?
C4 C3 H3A 110.9 . . ?
C4 C3 H3B 110.9 . . ?
C4 C3 C2 104.48(17) . . ?
C14 C13 C12 105.95(18) . . ?
C14 C13 C22 101.39(19) . . ?
C25 C13 C14 120.38(19) . . ?
C25 C13 C12 110.9(2) . . ?
C25 C13 C22 111.01(19) . . ?
C22 C13 C12 105.97(18) . . ?
C9 C14 C1 105.02(18) . . ?
C9 C14 H14 109.9 . . ?
C1 C14 H14 109.9 . . ?
C13 C14 C9 99.53(17) . . ?
C13 C14 C1 121.68(19) . . ?
C13 C14 H14 109.9 . . ?
C3 C2 C1 121.65(17) . . ?
C3 C2 C18 100.48(17) . . ?
C8 C2 C1 103.72(17) . . ?
C8 C2 C3 108.71(18) . . ?
C8 C2 C18 112.52(17) . . ?
C18 C2 C1 110.01(18) . . ?
S1 C15 H15A 110.0 . . ?
S1 C15 H15B 110.0 . . ?
H15A C15 H15B 108.4 . . ?
C16 C15 S1 108.4(2) . . ?
C16 C15 H15A 110.0 . . ?
C16 C15 H15B 110.0 . . ?
C9 C8 C2 104.87(18) . . ?
C9 C8 H8 105.3 . . ?
C9 C8 C7 121.21(18) . . ?
C2 C8 H8 105.3 . . ?
C7 C8 C2 113.66(18) . . ?
C7 C8 H8 105.3 . . ?
O3 C5 C6 103.11(17) . . ?
O3 C5 C18 116.37(18) . . ?
O3 C5 C4 114.29(19) . . ?
C18 C5 C6 107.91(18) . . ?
C4 C5 C6 112.18(19) . . ?
C4 C5 C18 103.09(17) . . ?
C8 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
C8 C7 C6 114.41(19) . . ?
H7A C7 H7B 107.6 . . ?
C6 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
C13 C25 H25A 109.5 . . ?
C13 C25 H25B 109.5 . . ?
C13 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O3 C20 C21 110.32(19) . . ?
O4 C20 O3 124.9(2) . . ?
O4 C20 C21 124.7(2) . . ?
C5 C6 C7 111.47(17) . . ?
C5 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C7 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C2 C18 H18A 111.7 . . ?
C2 C18 H18B 111.7 . . ?
C5 C18 C2 100.25(17) . . ?
C5 C18 H18A 111.7 . . ?
C5 C18 H18B 111.7 . . ?
H18A C18 H18B 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O7 C23 C24 111.0(3) . . ?
O8 C23 O7 122.5(3) . . ?
O8 C23 C24 126.5(3) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
H19A C19 H19B 120.0 . . ?
C4 C19 H19A 120.0 . . ?
C4 C19 H19B 120.0 . . ?
O7 C12 C13 105.59(19) . . ?
O7 C12 H12 109.2 . . ?
O7 C12 C11 109.39(19) . . ?
C13 C12 H12 109.2 . . ?
C11 C12 C13 114.0(2) . . ?
C11 C12 H12 109.2 . . ?
C10 C11 C12 122.7(2) . . ?
C10 C11 H11 118.7 . . ?
C12 C11 H11 118.7 . . ?
O5 C22 C13 109.61(19) . . ?
O6 C22 O5 122.1(2) . . ?
O6 C22 C13 128.3(2) . . ?
C15 C16 H16 118.4 . . ?
C17 C16 C15 123.2(3) . . ?
C17 C16 H16 118.4 . . ?
C16 C17 H17A 120.0 . . ?
C16 C17 H17B 120.0 . . ?
H17A C17 H17B 120.0 . . ?
C3 C4 C5 107.1(2) . . ?
C19 C4 C3 126.8(2) . . ?
C19 C4 C5 126.0(2) . . ?
O15 C48 C49 109.9(2) . . ?
O16 C48 O15 124.1(2) . . ?
O16 C48 C49 126.1(3) . . ?

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 C40 C41 C42 -113.3(3) . . . . ?
S2 C26 C39 C34 132.62(16) . . . . ?
S2 C26 C39 C38 -116.6(2) . . . . ?
O14 C47 C38 C50 24.2(3) . . . . ?
O14 C47 C38 C39 151.3(2) . . . . ?
O14 C47 C38 C37 -98.1(3) . . . . ?
O13 C47 C38 C50 -154.96(18) . . . . ?
O13 C47 C38 C39 -27.9(2) . . . . ?
O13 C47 C38 C37 82.7(2) . . . . ?
O13 C34 C33 C27 -68.6(2) . . . . ?
O13 C34 C33 C32 60.5(2) . . . . ?
O13 C34 C39 C26 85.06(19) . . . . ?
O13 C34 C39 C38 -39.4(2) . . . . ?
O15 C37 C36 C35 116.6(2) . . . . ?
O10 S2 C40 C41 -56.7(2) . . . . ?
O10 S2 C26 C27 169.05(15) . . . . ?
O10 S2 C26 C39 51.34(17) . . . . ?
O9 S2 C40 C41 72.1(2) . . . . ?
O9 S2 C26 C27 40.71(18) . . . . ?
O9 S2 C26 C39 -77.00(16) . . . . ?
C47 O13 C34 C35 -92.9(2) . . . . ?
C47 O13 C34 C33 135.09(19) . . . . ?
C47 O13 C34 C39 23.6(2) . . . . ?
C47 C38 C39 C34 39.8(2) . . . . ?
C47 C38 C39 C26 -73.8(2) . . . . ?
C47 C38 C37 O15 174.85(17) . . . . ?
C47 C38 C37 C36 -68.2(2) . . . . ?
C40 S2 C26 C27 -76.58(18) . . . . ?
C40 S2 C26 C39 165.71(15) . . . . ?
C30 O11 C45 O12 -6.5(3) . . . . ?
C30 O11 C45 C46 173.9(2) . . . . ?
C30 C31 C32 C33 -44.4(3) . . . . ?
C30 C29 C28 C27 -13.9(2) . . . . ?
O11 C30 C31 C32 -170.14(18) . . . . ?
O11 C30 C29 C44 37.2(3) . . . . ?
O11 C30 C29 C28 -145.96(19) . . . . ?
O11 C30 C43 C27 171.56(18) . . . . ?
C35 C34 C33 C27 167.16(19) . . . . ?
C35 C34 C33 C32 -63.7(3) . . . . ?
C35 C34 C39 C26 -161.64(17) . . . . ?
C35 C34 C39 C38 73.9(2) . . . . ?
C27 C26 C39 C34 7.9(2) . . . . ?
C27 C26 C39 C38 118.7(2) . . . . ?
C27 C33 C32 C31 36.0(3) . . . . ?
C31 C30 O11 C45 -175.55(19) . . . . ?
C31 C30 C29 C44 -79.3(3) . . . . ?
C31 C30 C29 C28 97.5(2) . . . . ?
C31 C30 C43 C27 -73.5(2) . . . . ?
C34 O13 C47 O14 -176.2(2) . . . . ?
C34 O13 C47 C38 3.1(2) . . . . ?
C34 C35 C36 C37 4.4(3) . . . . ?
C34 C33 C32 C31 -87.9(2) . . . . ?
C50 C38 C39 C34 162.9(2) . . . . ?
C50 C38 C39 C26 49.2(3) . . . . ?
C50 C38 C37 O15 52.2(3) . . . . ?
C50 C38 C37 C36 169.1(2) . . . . ?
C26 S2 C40 C41 -170.96(18) . . . . ?
C26 C27 C33 C34 -36.4(2) . . . . ?
C26 C27 C33 C32 -167.93(18) . . . . ?
C26 C27 C43 C30 178.80(17) . . . . ?
C26 C27 C28 C29 161.83(19) . . . . ?
C29 C30 O11 C45 63.7(3) . . . . ?
C29 C30 C31 C32 -45.5(3) . . . . ?
C29 C30 C43 C27 43.8(2) . . . . ?
C38 C37 C36 C35 -3.5(3) . . . . ?
C33 C27 C26 S2 -99.94(17) . . . . ?
C33 C27 C26 C39 17.1(2) . . . . ?
C33 C27 C43 C30 64.1(2) . . . . ?
C33 C27 C28 C29 -77.8(2) . . . . ?
C33 C34 C39 C26 -30.9(2) . . . . ?
C33 C34 C39 C38 -155.35(17) . . . . ?
C43 C30 O11 C45 -57.2(3) . . . . ?
C43 C30 C31 C32 66.9(2) . . . . ?
C43 C30 C29 C44 164.5(2) . . . . ?
C43 C30 C29 C28 -18.6(2) . . . . ?
C43 C27 C26 S2 139.41(16) . . . . ?
C43 C27 C26 C39 -103.51(19) . . . . ?
C43 C27 C33 C34 83.1(2) . . . . ?
C43 C27 C33 C32 -48.4(3) . . . . ?
C43 C27 C28 C29 40.2(2) . . . . ?
C44 C29 C28 C27 163.0(2) . . . . ?
C39 C34 C33 C27 42.4(2) . . . . ?
C39 C34 C33 C32 171.55(18) . . . . ?
C39 C38 C37 O15 -79.0(2) . . . . ?
C39 C38 C37 C36 38.0(3) . . . . ?
C28 C27 C26 S2 23.6(3) . . . . ?
C28 C27 C26 C39 140.7(2) . . . . ?
C28 C27 C33 C34 -167.85(18) . . . . ?
C28 C27 C33 C32 60.6(2) . . . . ?
C28 C27 C43 C30 -51.7(2) . . . . ?
C37 O15 C48 O16 12.6(4) . . . . ?
C37 O15 C48 C49 -167.3(2) . . . . ?
C37 C38 C39 C34 -69.6(2) . . . . ?
C37 C38 C39 C26 176.7(2) . . . . ?
C36 C35 C34 O13 70.3(3) . . . . ?
C36 C35 C34 C33 -163.3(2) . . . . ?
C36 C35 C34 C39 -41.5(3) . . . . ?
S1 C1 C14 C9 131.40(16) . . . . ?
S1 C1 C14 C13 -117.06(19) . . . . ?
S1 C1 C2 C3 15.6(2) . . . . ?
S1 C1 C2 C8 -106.93(16) . . . . ?
S1 C1 C2 C18 132.50(16) . . . . ?
S1 C15 C16 C17 105.3(3) . . . . ?
O3 C5 C6 C7 -171.71(19) . . . . ?
O3 C5 C18 C2 170.12(17) . . . . ?
O3 C5 C4 C3 -150.21(18) . . . . ?
O3 C5 C4 C19 28.6(3) . . . . ?
O2 S1 C1 C14 174.94(15) . . . . ?
O2 S1 C1 C2 -67.19(17) . . . . ?
O2 S1 C15 C16 62.4(2) . . . . ?
O5 C9 C14 C1 85.52(19) . . . . ?
O5 C9 C14 C13 -41.10(19) . . . . ?
O5 C9 C8 C2 -70.7(2) . . . . ?
O5 C9 C8 C7 59.6(2) . . . . ?
O7 C12 C11 C10 114.0(2) . . . . ?
C10 C9 C14 C1 -161.45(18) . . . . ?
C10 C9 C14 C13 71.9(2) . . . . ?
C10 C9 C8 C2 163.89(18) . . . . ?
C10 C9 C8 C7 -65.9(3) . . . . ?
O1 S1 C1 C14 -54.84(18) . . . . ?
O1 S1 C1 C2 63.03(16) . . . . ?
O1 S1 C15 C16 -66.2(2) . . . . ?
C9 O5 C22 C13 -4.4(2) . . . . ?
C9 O5 C22 O6 175.1(2) . . . . ?
C9 C10 C11 C12 0.8(3) . . . . ?
C9 C8 C7 C6 -93.3(2) . . . . ?
C1 S1 C15 C16 178.48(18) . . . . ?
C1 C2 C8 C9 -32.5(2) . . . . ?
C1 C2 C8 C7 -167.06(18) . . . . ?
C1 C2 C18 C5 -177.85(16) . . . . ?
C3 C2 C8 C9 -163.26(17) . . . . ?
C3 C2 C8 C7 62.2(2) . . . . ?
C3 C2 C18 C5 -48.41(19) . . . . ?
C13 C12 C11 C10 -4.0(3) . . . . ?
C14 C9 C8 C2 40.0(2) . . . . ?
C14 C9 C8 C7 170.26(18) . . . . ?
C14 C1 C2 C3 135.53(19) . . . . ?
C14 C1 C2 C8 13.0(2) . . . . ?
C14 C1 C2 C18 -107.60(19) . . . . ?
C14 C13 C12 O7 -78.2(2) . . . . ?
C14 C13 C12 C11 41.9(2) . . . . ?
C14 C13 C22 O5 -22.0(2) . . . . ?
C14 C13 C22 O6 158.5(2) . . . . ?
C2 C1 C14 C9 10.7(2) . . . . ?
C2 C1 C14 C13 122.2(2) . . . . ?
C2 C3 C4 C5 -7.6(2) . . . . ?
C2 C3 C4 C19 173.6(2) . . . . ?
C2 C8 C7 C6 33.1(3) . . . . ?
C15 S1 C1 C14 60.81(18) . . . . ?
C15 S1 C1 C2 178.68(15) . . . . ?
C8 C9 C14 C1 -31.2(2) . . . . ?
C8 C9 C14 C13 -157.78(17) . . . . ?
C8 C2 C18 C5 67.1(2) . . . . ?
C8 C7 C6 C5 -41.1(3) . . . . ?
C5 O3 C20 O4 4.9(4) . . . . ?
C5 O3 C20 C21 -174.3(2) . . . . ?
C25 C13 C14 C9 160.36(19) . . . . ?
C25 C13 C14 C1 46.0(3) . . . . ?
C25 C13 C12 O7 54.0(2) . . . . ?
C25 C13 C12 C11 174.1(2) . . . . ?
C25 C13 C22 O5 -151.10(18) . . . . ?
C25 C13 C22 O6 29.4(3) . . . . ?
C20 O3 C5 C6 -176.9(2) . . . . ?
C20 O3 C5 C18 -59.1(3) . . . . ?
C20 O3 C5 C4 61.0(3) . . . . ?
C6 C5 C18 C2 -74.6(2) . . . . ?
C6 C5 C4 C3 92.9(2) . . . . ?
C6 C5 C4 C19 -88.3(3) . . . . ?
C18 C2 C8 C9 86.3(2) . . . . ?
C18 C2 C8 C7 -48.2(3) . . . . ?
C18 C5 C6 C7 64.6(2) . . . . ?
C18 C5 C4 C3 -23.0(2) . . . . ?
C18 C5 C4 C19 155.8(2) . . . . ?
C23 O7 C12 C13 -152.7(2) . . . . ?
C23 O7 C12 C11 84.2(3) . . . . ?
C12 O7 C23 O8 -5.8(4) . . . . ?
C12 O7 C23 C24 173.1(2) . . . . ?
C12 C13 C14 C9 -72.9(2) . . . . ?
C12 C13 C14 C1 172.71(19) . . . . ?
C12 C13 C22 O5 88.4(2) . . . . ?
C12 C13 C22 O6 -91.1(3) . . . . ?
C11 C10 C9 O5 74.4(2) . . . . ?
C11 C10 C9 C14 -36.4(3) . . . . ?
C11 C10 C9 C8 -157.8(2) . . . . ?
C22 O5 C9 C10 -86.2(2) . . . . ?
C22 O5 C9 C14 29.3(2) . . . . ?
C22 O5 C9 C8 141.04(18) . . . . ?
C22 C13 C14 C9 37.53(19) . . . . ?
C22 C13 C14 C1 -76.8(2) . . . . ?
C22 C13 C12 O7 174.6(2) . . . . ?
C22 C13 C12 C11 -65.3(3) . . . . ?
C4 C3 C2 C1 156.01(18) . . . . ?
C4 C3 C2 C8 -83.8(2) . . . . ?
C4 C3 C2 C18 34.5(2) . . . . ?
C4 C5 C6 C7 -48.3(3) . . . . ?
C4 C5 C18 C2 44.20(19) . . . . ?
C48 O15 C37 C38 -110.8(2) . . . . ?
C48 O15 C37 C36 125.7(2) . . . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.360
_oxdiff_exptl_absorpt_empirical_full_min 0.832
