# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_20230363_auto
_database_code_depnum_ccdc_archive 'CCDC 2348055'
loop_
_audit_author_name
_audit_author_address
'product zyh'
;Zhengzhou university
China
;
_audit_update_record             
;
2024-04-13 deposited with the CCDC.	2024-07-19 downloaded from the CCDC.
;
_audit_creation_date             2023-03-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H17 N O5 S'
_chemical_formula_sum            'C16 H17 N O5 S'
_chemical_formula_weight         335.36
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N1O1S1
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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.1853(4)
_cell_length_b                   10.3385(4)
_cell_length_c                   18.6161(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1575.37(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2803
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.4850
_cell_measurement_theta_min      4.7570
_shelx_estimated_absorpt_T_max   0.821
_shelx_estimated_absorpt_T_min   0.761
_exptl_absorpt_coefficient_mu    2.060
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5663
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.279
_diffrn_reflns_theta_min         4.751
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00  36.00   1.00    1.00    --  -33.50  77.00   0.00   98
  2  ω   -102.00 -15.00   1.00    1.00    --  -33.50 -57.00 -30.00   87
  3  ω   -108.00 -35.00   1.00    1.00    --  -33.50 178.00   0.00   73
  4  ω     61.00 109.00   1.00    1.00    --   36.47 178.00   0.00   48
  5  ω     66.00 104.00   1.00    1.00    --   36.47 178.00-120.00   38
  6  ω     47.00 101.00   1.00    4.50    --  108.00-111.00  90.00   54
  7  ω     79.00 105.00   1.00    4.50    --  108.00 -94.00  90.00   26
  8  ω     83.00 164.00   1.00    4.50    --  108.00  30.00 120.00   81
  9  ω    112.00 166.00   1.00    4.50    --  108.00  77.00 175.00   54
 10  ω     44.00 129.00   1.00    4.50    --  108.00 -30.00-120.00   85
 11  ω    102.00 177.00   1.00    4.50    --  108.00  77.00-150.00   75
 12  ω     93.00 178.00   1.00    4.50    --  108.00  45.00  60.00   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0589961000
_diffrn_orient_matrix_UB_12      0.0177552000
_diffrn_orient_matrix_UB_13      -0.0780233000
_diffrn_orient_matrix_UB_21      0.1475300000
_diffrn_orient_matrix_UB_22      -0.0786520000
_diffrn_orient_matrix_UB_23      -0.0270563000
_diffrn_orient_matrix_UB_31      -0.1006903000
_diffrn_orient_matrix_UB_32      -0.1253907000
_diffrn_orient_matrix_UB_33      0.0059954000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                2608
_reflns_number_total             2937
_reflns_odcompleteness_completeness 99.88
_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 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 976 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.008(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2937
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0401
_refine_ls_restrained_S_all      1.035
_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)+(0.0640P)²+0.0015P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1125
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O2-H2A
 0.9 with sigma of 0.02
 H1A-O1
 0.9 with sigma of 0.02
3.a Riding coordinates:
 O2(H2A)
3.b Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C11(H11), C12(H12), C14(H14), C15(H15)
3.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
C1 C 0.5747(4) 0.2629(4) 0.7712(2) 0.0510(9) Uani 1 1 d . . . . .
H1 H 0.5450 0.2397 0.7219 0.061 Uiso 1 1 calc R . . . .
C2 C 0.4508(4) 0.3570(3) 0.8036(2) 0.0507(8) Uani 1 1 d . . . . .
H2 H 0.3811 0.3129 0.8387 0.061 Uiso 1 1 calc R . . . .
C3 C 0.5547(4) 0.4577(3) 0.83977(19) 0.0446(7) Uani 1 1 d . . . . .
C4 C 0.7164(4) 0.4445(4) 0.81843(19) 0.0468(8) Uani 1 1 d . . . . .
C5 C 0.8355(4) 0.5292(4) 0.8424(2) 0.0556(9) Uani 1 1 d . . . . .
H5 H 0.9443 0.5185 0.8293 0.067 Uiso 1 1 calc R . . . .
C6 C 0.7876(5) 0.6311(4) 0.8869(2) 0.0555(9) Uani 1 1 d . . . . .
H6 H 0.8650 0.6906 0.9025 0.067 Uiso 1 1 calc R . . . .
C7 C 0.6268(5) 0.6447(4) 0.9081(2) 0.0532(8) Uani 1 1 d . . . . .
C8 C 0.5100(4) 0.5570(4) 0.8848(2) 0.0527(8) Uani 1 1 d . . . . .
H8 H 0.4019 0.5654 0.8995 0.063 Uiso 1 1 calc R . . . .
C9 C 0.6796(7) 0.8430(5) 0.9699(3) 0.0909(17) Uani 1 1 d . . . . .
H9A H 0.7203 0.8820 0.9266 0.136 Uiso 1 1 calc GR . . . .
H9B H 0.7693 0.8088 0.9971 0.136 Uiso 1 1 calc GR . . . .
H9C H 0.6234 0.9070 0.9979 0.136 Uiso 1 1 calc GR . . . .
C10 C 0.8519(4) 0.4530(4) 0.6517(2) 0.0505(8) Uani 1 1 d . . . . .
C11 C 0.7345(6) 0.4508(5) 0.5981(3) 0.0677(11) Uani 1 1 d . . . . .
H11 H 0.6648 0.3803 0.5935 0.081 Uiso 1 1 calc R . . . .
C12 C 0.7221(7) 0.5548(5) 0.5516(3) 0.0758(13) Uani 1 1 d . . . . .
H12 H 0.6447 0.5524 0.5151 0.091 Uiso 1 1 calc R . . . .
C13 C 0.8208(6) 0.6610(5) 0.5580(2) 0.0660(11) Uani 1 1 d . . . . .
C14 C 0.9362(7) 0.6621(5) 0.6120(2) 0.0757(13) Uani 1 1 d . . . . .
H14 H 1.0032 0.7341 0.6174 0.091 Uiso 1 1 calc R . . . .
C15 C 0.9546(6) 0.5582(5) 0.6583(2) 0.0672(11) Uani 1 1 d . . . . .
H15 H 1.0352 0.5594 0.6935 0.081 Uiso 1 1 calc R . . . .
C16 C 0.8013(9) 0.7741(6) 0.5080(3) 0.0963(18) Uani 1 1 d . . . . .
H16A H 0.8799 0.8395 0.5200 0.144 Uiso 1 1 calc GR . . . .
H16B H 0.6931 0.8089 0.5127 0.144 Uiso 1 1 calc GR . . . .
H16C H 0.8184 0.7461 0.4594 0.144 Uiso 1 1 calc GR . . . .
N7 N 0.7316(3) 0.3348(3) 0.77322(17) 0.0528(7) Uani 1 1 d . . . . .
O1 O 0.5843(5) 0.1534(3) 0.81485(19) 0.0735(9) Uani 1 1 d D . . . .
H1A H 0.606(7) 0.093(4) 0.783(2) 0.090(18) Uiso 1 1 d D . . . .
O2 O 0.3546(3) 0.4170(3) 0.74940(18) 0.0665(8) Uani 1 1 d D . . . .
H2A H 0.2542 0.3856 0.7527 0.14(3) Uiso 1 1 d DR . . . .
O3 O 0.8342(3) 0.2042(3) 0.67335(17) 0.0616(7) Uani 1 1 d . . . . .
O4 O 1.0262(3) 0.3350(3) 0.74521(17) 0.0621(7) Uani 1 1 d . . . . .
O5 O 0.5704(4) 0.7416(3) 0.95213(19) 0.0733(9) Uani 1 1 d . . . . .
S1 S 0.87154(9) 0.32133(8) 0.71068(5) 0.0490(2) 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
C1 H1 0.9800 . ?
C1 C2 1.529(5) . ?
C1 N7 1.484(4) . ?
C1 O1 1.396(5) . ?
C2 H2 0.9800 . ?
C2 C3 1.504(5) . ?
C2 O2 1.422(5) . ?
C3 C4 1.389(5) . ?
C3 C8 1.375(5) . ?
C4 C5 1.384(5) . ?
C4 N7 1.418(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.397(6) . ?
C6 H6 0.9300 . ?
C6 C7 1.381(6) . ?
C7 C8 1.387(5) . ?
C7 O5 1.375(5) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C9 O5 1.417(6) . ?
C10 C11 1.385(6) . ?
C10 C15 1.380(6) . ?
C10 S1 1.756(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.384(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.368(7) . ?
C13 C14 1.380(7) . ?
C13 C16 1.502(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.386(7) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N7 S1 1.639(3) . ?
O1 H1A 0.88(2) . ?
O2 H2A 0.8857 . ?
O3 S1 1.429(3) . ?
O4 S1 1.427(3) . ?

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
C2 C1 H1 111.1 . . ?
N7 C1 H1 111.1 . . ?
N7 C1 C2 104.2(3) . . ?
O1 C1 H1 111.1 . . ?
O1 C1 C2 108.9(3) . . ?
O1 C1 N7 110.1(3) . . ?
C1 C2 H2 110.7 . . ?
C3 C2 C1 104.0(3) . . ?
C3 C2 H2 110.7 . . ?
O2 C2 C1 111.4(3) . . ?
O2 C2 H2 110.7 . . ?
O2 C2 C3 109.2(3) . . ?
C4 C3 C2 110.0(3) . . ?
C8 C3 C2 129.7(3) . . ?
C8 C3 C4 120.1(3) . . ?
C3 C4 N7 109.4(3) . . ?
C5 C4 C3 121.1(4) . . ?
C5 C4 N7 129.5(3) . . ?
C4 C5 H5 121.0 . . ?
C4 C5 C6 118.1(4) . . ?
C6 C5 H5 121.0 . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 120.9(4) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C8 120.1(4) . . ?
O5 C7 C6 124.3(4) . . ?
O5 C7 C8 115.6(4) . . ?
C3 C8 C7 119.7(4) . . ?
C3 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O5 C9 H9A 109.5 . . ?
O5 C9 H9B 109.5 . . ?
O5 C9 H9C 109.5 . . ?
C11 C10 S1 120.1(3) . . ?
C15 C10 C11 119.9(4) . . ?
C15 C10 S1 120.0(3) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 C10 119.3(4) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 H12 119.1 . . ?
C13 C12 C11 121.7(4) . . ?
C13 C12 H12 119.1 . . ?
C12 C13 C14 118.3(4) . . ?
C12 C13 C16 120.5(5) . . ?
C14 C13 C16 121.2(5) . . ?
C13 C14 H14 119.3 . . ?
C13 C14 C15 121.5(4) . . ?
C15 C14 H14 119.3 . . ?
C10 C15 C14 119.3(4) . . ?
C10 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
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 . . ?
C1 N7 S1 123.0(3) . . ?
C4 N7 C1 109.9(3) . . ?
C4 N7 S1 123.4(2) . . ?
C1 O1 H1A 101(4) . . ?
C2 O2 H2A 107.7 . . ?
C7 O5 C9 117.8(4) . . ?
N7 S1 C10 108.30(17) . . ?
O3 S1 C10 109.47(18) . . ?
O3 S1 N7 105.55(17) . . ?
O4 S1 C10 106.63(19) . . ?
O4 S1 N7 106.96(17) . . ?
O4 S1 O3 119.50(18) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A O2 0.88(2) 1.94(3) 2.766(4) 155(5) 4_646
O2 H2A O4 0.89 1.94 2.819(4) 170.0 1_455

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
C1 C2 C3 C4 12.3(4) . . . . ?
C1 C2 C3 C8 -171.2(4) . . . . ?
C1 N7 S1 C10 98.8(3) . . . . ?
C1 N7 S1 O3 -18.3(4) . . . . ?
C1 N7 S1 O4 -146.6(3) . . . . ?
C2 C1 N7 C4 14.1(4) . . . . ?
C2 C1 N7 S1 -144.7(3) . . . . ?
C2 C3 C4 C5 177.7(4) . . . . ?
C2 C3 C4 N7 -3.8(4) . . . . ?
C2 C3 C8 C7 -175.5(4) . . . . ?
C3 C4 C5 C6 -2.0(6) . . . . ?
C3 C4 N7 C1 -6.8(4) . . . . ?
C3 C4 N7 S1 151.9(3) . . . . ?
C4 C3 C8 C7 0.7(6) . . . . ?
C4 C5 C6 C7 1.9(6) . . . . ?
C4 N7 S1 C10 -57.1(3) . . . . ?
C4 N7 S1 O3 -174.3(3) . . . . ?
C4 N7 S1 O4 57.5(3) . . . . ?
C5 C4 N7 C1 171.6(4) . . . . ?
C5 C4 N7 S1 -29.7(6) . . . . ?
C5 C6 C7 C8 -0.5(6) . . . . ?
C5 C6 C7 O5 179.5(4) . . . . ?
C6 C7 C8 C3 -0.8(6) . . . . ?
C6 C7 O5 C9 8.1(6) . . . . ?
C8 C3 C4 C5 0.8(6) . . . . ?
C8 C3 C4 N7 179.3(3) . . . . ?
C8 C7 O5 C9 -171.9(4) . . . . ?
C10 C11 C12 C13 -1.2(8) . . . . ?
C11 C10 C15 C14 1.4(7) . . . . ?
C11 C10 S1 N7 -81.0(4) . . . . ?
C11 C10 S1 O3 33.6(4) . . . . ?
C11 C10 S1 O4 164.2(3) . . . . ?
C11 C12 C13 C14 0.7(8) . . . . ?
C11 C12 C13 C16 -178.2(5) . . . . ?
C12 C13 C14 C15 0.9(8) . . . . ?
C13 C14 C15 C10 -2.0(8) . . . . ?
C15 C10 C11 C12 0.1(7) . . . . ?
C15 C10 S1 N7 99.7(4) . . . . ?
C15 C10 S1 O3 -145.7(3) . . . . ?
C15 C10 S1 O4 -15.1(4) . . . . ?
C16 C13 C14 C15 179.8(5) . . . . ?
N7 C1 C2 C3 -15.4(4) . . . . ?
N7 C1 C2 O2 102.1(3) . . . . ?
N7 C4 C5 C6 179.8(4) . . . . ?
O1 C1 C2 C3 102.0(3) . . . . ?
O1 C1 C2 O2 -140.5(3) . . . . ?
O1 C1 N7 C4 -102.6(3) . . . . ?
O1 C1 N7 S1 98.6(4) . . . . ?
O2 C2 C3 C4 -106.7(4) . . . . ?
O2 C2 C3 C8 69.8(5) . . . . ?
O5 C7 C8 C3 179.2(4) . . . . ?
S1 C10 C11 C12 -179.2(4) . . . . ?
S1 C10 C15 C14 -179.2(4) . . . . ?

_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 1.171
_oxdiff_exptl_absorpt_empirical_full_min 0.919
####################################################################### 
# 
# 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_20230472_auto
_database_code_depnum_ccdc_archive 'CCDC 2348058'
loop_
_audit_author_name
_audit_author_address
zyh
;Zhengzhou university
China
;
_audit_update_record             
;
2024-04-13 deposited with the CCDC.	2024-07-19 downloaded from the CCDC.
;
_audit_creation_date             2023-04-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H23 Cl N2 O7 S'
_chemical_formula_sum            'C24 H23 Cl N2 O7 S'
_chemical_formula_weight         518.95
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N1O1S3Cl1
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      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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.80415(14)
_cell_length_b                   13.7157(2)
_cell_length_c                   22.4935(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2407.68(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3496
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.3500
_cell_measurement_theta_min      3.7630
_shelx_estimated_absorpt_T_max   0.817
_shelx_estimated_absorpt_T_min   0.678
_exptl_absorpt_coefficient_mu    2.634
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79349
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8864
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.361
_diffrn_reflns_theta_min         3.775
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -15.90   0.70    4.00    --  -33.50 -57.00   0.00  123
  2  ω   -108.00 -35.90   0.70    4.00    --  -33.50 178.00 150.00  103
  3  ω   -104.00 -11.60   0.70    4.00    --  -33.50 -37.00 -90.00  132
  4  ω     61.00 110.00   0.70    4.00    --   36.47 178.00 120.00   70
  5  ω     46.00 111.10   0.70    4.00    --   36.47-162.00-120.00   93
  6  ω     36.00 152.20   0.70   14.00    --  108.00 -15.00  90.00  166
  7  ω     39.00 124.40   0.70   14.00    --  108.00 -45.00-150.00  122
  8  ω     63.00 122.50   0.70   14.00    --  108.00 -61.00-120.00   85
  9  ω     41.00 107.50   0.70   14.00    --  108.00 -61.00 150.00   95
 10  ω     69.00 103.30   0.70   14.00    --  108.00 -94.00  30.00   49
 11  ω    140.00 172.90   0.70   14.00    --  108.00  61.00   0.00   47
 12  ω     39.00 105.50   0.70   14.00    --  108.00 -94.00  90.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0017245000
_diffrn_orient_matrix_UB_12      -0.0308683000
_diffrn_orient_matrix_UB_13      -0.0658448000
_diffrn_orient_matrix_UB_21      -0.0293131000
_diffrn_orient_matrix_UB_22      -0.1067317000
_diffrn_orient_matrix_UB_23      0.0187710000
_diffrn_orient_matrix_UB_31      -0.1951872000
_diffrn_orient_matrix_UB_32      0.0163903000
_diffrn_orient_matrix_UB_33      -0.0022148000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.729
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                3855
_reflns_number_total             4519
_reflns_odcompleteness_completeness 99.88
_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 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1342 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.063(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         4519
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0482
_refine_ls_restrained_S_all      1.045
_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)+(0.0576P)²+0.3496P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1272
_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, All O(H) groups
2. Restrained distances
 N1-H1
 0.87 with sigma of 0.02
 C9-C11A
 1.54 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(Cl1A) \\sim Ueq, Uanis(Cl1) \\sim Ueq, Uanis(C13A) \\sim Ueq, Uanis(C13)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(Cl1) = Uanis(Cl1A)
Uanis(C13) = Uanis(C13A)
Uanis(C12) = Uanis(C12A)
Uanis(C11) = Uanis(C11A)
Uanis(C16) = Uanis(C16A)
Uanis(C15) = Uanis(C15A)
Uanis(C14) = Uanis(C14A)
4. Others
 Sof(H9B)=Sof(C11A)=Sof(C12A)=Sof(H12A)=Sof(C13A)=Sof(H13A)=Sof(C14A)=
 Sof(H14A)=Sof(C15A)=Sof(C16A)=Sof(H16A)=Sof(Cl1A)=1-FVAR(1)
 Sof(H9A)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(C14)=Sof(H14)=Sof(C15)=Sof(H15)=
 Sof(C16)=Sof(H16)=Sof(C11)=Sof(Cl1)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9A), C9(H9B)
5.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C12A(H12A), C13A(H13A), C14A(H14A), C16A(H16A),
 C12(H12), C14(H14), C15(H15), C16(H16), C19(H19), C20(H20), C22(H22), C23(H23)
5.d Fitted hexagon refined as free rotating group:
 C11A(C12A,C13A,C14A,C15A,C16A), C12(C13,C14,C15,C16,C11)
5.e Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C24(H24A,H24B,H24C)
5.f Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
C1 C 1.0379(6) 0.6020(3) 0.65114(19) 0.0470(10) Uani 1 1 d . . . . .
C2 C 0.9734(8) 0.6955(3) 0.6421(2) 0.0652(14) Uani 1 1 d . . . . .
H2 H 0.9715 0.7397 0.6735 0.078 Uiso 1 1 calc R . . . .
C3 C 0.9125(9) 0.7232(4) 0.5874(3) 0.0731(17) Uani 1 1 d . . . . .
H3 H 0.8681 0.7855 0.5823 0.088 Uiso 1 1 calc R . . . .
C4 C 0.9167(8) 0.6592(4) 0.5399(2) 0.0609(13) Uani 1 1 d . . . . .
C5 C 0.9745(7) 0.5653(3) 0.5484(2) 0.0516(11) Uani 1 1 d . . . . .
H5 H 0.9752 0.5217 0.5168 0.062 Uiso 1 1 calc R . . . .
C6 C 1.0323(6) 0.5350(3) 0.60461(18) 0.0442(9) Uani 1 1 d . . . . .
C7 C 1.0798(6) 0.4312(3) 0.6139(2) 0.0493(11) Uani 1 1 d . . . . .
C8 C 0.9963(7) 0.3503(3) 0.5764(2) 0.0502(11) Uani 1 1 d . . . . .
H8 H 0.9903 0.3718 0.5349 0.060 Uiso 1 1 calc R . . . .
C9 C 0.8104(6) 0.3310(3) 0.59971(19) 0.0462(10) Uani 1 1 d D . . . .
H9A H 0.8164 0.3273 0.6432 0.055 Uiso 0.878(3) 1 calc R . P A 1
H9B H 0.8069 0.3335 0.6432 0.055 Uiso 0.122(3) 1 calc R . P A 2
C10 C 0.7533(8) 0.2307(3) 0.5771(2) 0.0581(13) Uani 1 1 d . . . . .
H10A H 0.7472 0.2320 0.5340 0.070 Uiso 1 1 calc R . . . .
H10B H 0.8379 0.1823 0.5884 0.070 Uiso 1 1 calc R . . . .
C11A C 0.704(7) 0.408(4) 0.5739(19) 0.0435(14) Uani 0.122(3) 1 d D . P A 2
C12A C 0.657(7) 0.407(3) 0.5144(18) 0.0542(15) Uani 0.122(3) 1 d G . P A 2
H12A H 0.7043 0.3611 0.4887 0.065 Uiso 0.122(3) 1 calc R . P A 2
C13A C 0.538(6) 0.474(2) 0.4932(13) 0.0582(15) Uani 0.122(3) 1 d G U P A 2
H13A H 0.5065 0.4732 0.4533 0.070 Uiso 0.122(3) 1 calc R . P A 2
C14A C 0.467(5) 0.542(2) 0.5316(16) 0.0595(15) Uani 0.122(3) 1 d G . P A 2
H14A H 0.3878 0.5873 0.5174 0.071 Uiso 0.122(3) 1 calc R . P A 2
C15A C 0.514(6) 0.543(3) 0.5911(15) 0.0563(14) Uani 0.122(3) 1 d G . P A 2
C16A C 0.633(7) 0.476(4) 0.6123(13) 0.0463(12) Uani 0.122(3) 1 d G . P A 2
H16A H 0.6645 0.4769 0.6522 0.056 Uiso 0.122(3) 1 calc R . P A 2
C12 C 0.6226(8) 0.4219(3) 0.52592(17) 0.0542(15) Uani 0.878(3) 1 d . . P A 1
H12 H 0.6565 0.3777 0.4969 0.065 Uiso 0.878(3) 1 calc R . P A 1
C13 C 0.5139(7) 0.4985(3) 0.51131(14) 0.0582(15) Uani 0.878(3) 1 d G U P A 1
C14 C 0.4633(6) 0.5646(2) 0.55474(18) 0.0595(15) Uani 0.878(3) 1 d G . P A 1
H14 H 0.3905 0.6158 0.5450 0.071 Uiso 0.878(3) 1 calc R . P A 1
C15 C 0.5215(7) 0.5541(3) 0.61280(16) 0.0563(14) Uani 0.878(3) 1 d G . P A 1
H15 H 0.4876 0.5983 0.6419 0.068 Uiso 0.878(3) 1 calc R . P A 1
C16 C 0.6303(8) 0.4775(5) 0.62741(14) 0.0463(12) Uani 0.878(3) 1 d G . P A 1
H16 H 0.6692 0.4704 0.6662 0.056 Uiso 0.878(3) 1 calc R . P A 1
C11 C 0.6808(8) 0.4114(4) 0.58397(19) 0.0435(14) Uani 0.878(3) 1 d G . P A 1
C17 C 0.8768(12) 0.6378(6) 0.4354(3) 0.099(2) Uani 1 1 d . . . . .
H17A H 0.8082 0.5800 0.4392 0.148 Uiso 1 1 calc GR . . . .
H17B H 0.9948 0.6197 0.4304 0.148 Uiso 1 1 calc GR . . . .
H17C H 0.8394 0.6744 0.4015 0.148 Uiso 1 1 calc GR . . . .
C18 C 0.8460(5) 0.5158(3) 0.77547(18) 0.0424(9) Uani 1 1 d . . . . .
C19 C 0.6884(6) 0.5548(4) 0.7874(2) 0.0529(11) Uani 1 1 d . . . . .
H19 H 0.6764 0.6216 0.7929 0.064 Uiso 1 1 calc R . . . .
C20 C 0.5471(6) 0.4944(4) 0.7913(2) 0.0594(12) Uani 1 1 d . . . . .
H20 H 0.4404 0.5211 0.8000 0.071 Uiso 1 1 calc R . . . .
C21 C 0.5617(6) 0.3948(4) 0.7825(2) 0.0528(11) Uani 1 1 d . . . . .
C22 C 0.7233(6) 0.3567(3) 0.7706(2) 0.0509(11) Uani 1 1 d . . . . .
H22 H 0.7358 0.2899 0.7647 0.061 Uiso 1 1 calc R . . . .
C23 C 0.8647(6) 0.4161(3) 0.7674(2) 0.0472(10) Uani 1 1 d . . . . .
H23 H 0.9723 0.3896 0.7599 0.057 Uiso 1 1 calc R . . . .
C24 C 0.4065(8) 0.3298(5) 0.7847(3) 0.0775(17) Uani 1 1 d . . . . .
H24A H 0.3744 0.3116 0.7450 0.116 Uiso 1 1 calc GR . . . .
H24B H 0.3135 0.3640 0.8032 0.116 Uiso 1 1 calc GR . . . .
H24C H 0.4326 0.2723 0.8072 0.116 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.4384(3) 0.50891(11) 0.43981(8) 0.0952(8) Uani 0.878(3) 1 d . U P A 1
Cl1A Cl 0.455(2) 0.6316(8) 0.6410(6) 0.0952(8) Uani 0.122(3) 1 d . U P A 2
N1 N 1.1163(5) 0.5771(3) 0.70633(17) 0.0488(9) Uani 1 1 d D . . . .
H1 H 1.158(6) 0.520(2) 0.707(2) 0.057(16) Uiso 1 1 d D . . . .
N2 N 0.5832(8) 0.2021(3) 0.6016(2) 0.0713(14) Uani 1 1 d . . . . .
O1 O 0.9689(5) 0.6915(2) 0.77711(16) 0.0648(9) Uani 1 1 d . . . . .
O2 O 1.1513(5) 0.5575(3) 0.81273(15) 0.0657(10) Uani 1 1 d . . . . .
O3 O 1.1758(5) 0.4058(3) 0.65347(16) 0.0596(9) Uani 1 1 d . . . . .
O4 O 1.0974(6) 0.2660(3) 0.57969(18) 0.0696(11) Uani 1 1 d . . . . .
H4 H 1.1657 0.2712 0.6072 0.104 Uiso 1 1 calc GR . . . .
O5 O 0.8593(7) 0.6953(3) 0.48725(18) 0.0864(14) Uani 1 1 d . . . . .
O6 O 0.5403(8) 0.2329(3) 0.6491(2) 0.0979(16) Uani 1 1 d . . . . .
O7 O 0.5016(8) 0.1431(4) 0.5730(2) 0.118(2) Uani 1 1 d . . . . .
S1 S 1.02642(14) 0.59301(9) 0.77212(5) 0.0480(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
C1 C2 1.393(7) . ?
C1 C6 1.394(6) . ?
C1 N1 1.425(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.372(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(8) . ?
C4 C5 1.378(7) . ?
C4 O5 1.360(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.405(6) . ?
C6 C7 1.485(6) . ?
C7 C8 1.538(6) . ?
C7 O3 1.215(6) . ?
C8 H8 0.9800 . ?
C8 C9 1.565(7) . ?
C8 O4 1.402(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 C10 1.533(6) . ?
C9 C11A 1.46(2) . ?
C9 C11 1.537(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 N2 1.490(8) . ?
C11A C12A 1.3900 . ?
C11A C16A 1.3900 . ?
C12A H12A 0.9300 . ?
C12A C13A 1.3900 . ?
C13A H13A 0.9300 . ?
C13A C14A 1.3900 . ?
C14A H14A 0.9300 . ?
C14A C15A 1.3900 . ?
C15A C16A 1.3900 . ?
C15A Cl1A 1.71(3) . ?
C16A H16A 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.3900 . ?
C12 C11 1.3900 . ?
C13 C14 1.3900 . ?
C13 Cl1 1.719(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.3900 . ?
C15 H15 0.9300 . ?
C15 C16 1.3900 . ?
C16 H16 0.9300 . ?
C16 C11 1.3900 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C17 O5 1.415(8) . ?
C18 C19 1.368(6) . ?
C18 C23 1.388(6) . ?
C18 S1 1.763(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.381(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.386(7) . ?
C21 C22 1.391(7) . ?
C21 C24 1.505(7) . ?
C22 H22 0.9300 . ?
C22 C23 1.373(6) . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
N1 H1 0.85(3) . ?
N1 S1 1.652(4) . ?
N2 O6 1.199(6) . ?
N2 O7 1.213(6) . ?
O1 S1 1.428(4) . ?
O2 S1 1.422(4) . ?
O4 H4 0.8200 . ?

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
C2 C1 C6 119.1(4) . . ?
C2 C1 N1 120.2(4) . . ?
C6 C1 N1 120.7(4) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.7(5) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(5) . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.5(5) . . ?
O5 C4 C3 115.7(5) . . ?
O5 C4 C5 124.8(5) . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.5(4) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 119.4(4) . . ?
C1 C6 C7 121.3(4) . . ?
C5 C6 C7 119.3(4) . . ?
C6 C7 C8 120.6(4) . . ?
O3 C7 C6 122.1(4) . . ?
O3 C7 C8 117.1(4) . . ?
C7 C8 H8 109.0 . . ?
C7 C8 C9 109.3(4) . . ?
C9 C8 H8 109.0 . . ?
O4 C8 C7 109.1(4) . . ?
O4 C8 H8 109.0 . . ?
O4 C8 C9 111.4(4) . . ?
C8 C9 H9A 107.4 . . ?
C8 C9 H9B 110.8 . . ?
C10 C9 C8 108.1(4) . . ?
C10 C9 H9A 107.4 . . ?
C10 C9 H9B 110.8 . . ?
C10 C9 C11 112.1(5) . . ?
C11A C9 C8 106(3) . . ?
C11A C9 H9B 110.8 . . ?
C11A C9 C10 111(3) . . ?
C11 C9 C8 114.3(4) . . ?
C11 C9 H9A 107.4 . . ?
C9 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
N2 C10 C9 111.9(4) . . ?
N2 C10 H10A 109.2 . . ?
N2 C10 H10B 109.2 . . ?
C12A C11A C9 122(3) . . ?
C12A C11A C16A 120.0 . . ?
C16A C11A C9 118(3) . . ?
C11A C12A H12A 120.0 . . ?
C13A C12A C11A 120.0 . . ?
C13A C12A H12A 120.0 . . ?
C12A C13A H13A 120.0 . . ?
C14A C13A C12A 120.0 . . ?
C14A C13A H13A 120.0 . . ?
C13A C14A H14A 120.0 . . ?
C13A C14A C15A 120.0 . . ?
C15A C14A H14A 120.0 . . ?
C14A C15A Cl1A 125(2) . . ?
C16A C15A C14A 120.0 . . ?
C16A C15A Cl1A 115(2) . . ?
C11A C16A H16A 120.0 . . ?
C15A C16A C11A 120.0 . . ?
C15A C16A H16A 120.0 . . ?
C13 C12 H12 120.0 . . ?
C13 C12 C11 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.0 . . ?
C12 C13 Cl1 119.6(3) . . ?
C14 C13 Cl1 120.4(3) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 120.0 . . ?
C11 C16 C15 120.0 . . ?
C11 C16 H16 120.0 . . ?
C12 C11 C9 120.4(3) . . ?
C16 C11 C9 119.5(3) . . ?
C16 C11 C12 120.0 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O5 C17 H17A 109.5 . . ?
O5 C17 H17B 109.5 . . ?
O5 C17 H17C 109.5 . . ?
C19 C18 C23 120.3(4) . . ?
C19 C18 S1 119.5(4) . . ?
C23 C18 S1 120.2(3) . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.8(4) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 119.5 . . ?
C19 C20 C21 121.1(4) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 C22 118.2(4) . . ?
C20 C21 C24 120.9(5) . . ?
C22 C21 C24 120.9(5) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 C21 121.0(4) . . ?
C23 C22 H22 119.5 . . ?
C18 C23 H23 120.2 . . ?
C22 C23 C18 119.6(4) . . ?
C22 C23 H23 120.2 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1 N1 H1 113(4) . . ?
C1 N1 S1 124.5(3) . . ?
S1 N1 H1 106(4) . . ?
O6 N2 C10 119.0(5) . . ?
O6 N2 O7 124.2(6) . . ?
O7 N2 C10 116.6(5) . . ?
C8 O4 H4 109.5 . . ?
C4 O5 C17 118.8(5) . . ?
N1 S1 C18 107.4(2) . . ?
O1 S1 C18 108.3(2) . . ?
O1 S1 N1 109.2(2) . . ?
O2 S1 C18 108.3(2) . . ?
O2 S1 N1 103.8(2) . . ?
O2 S1 O1 119.3(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 O1 0.93 2.42 3.037(7) 123.5 .
C8 H8 O7 0.98 2.44 3.361(7) 157.2 3_556
N1 H1 O3 0.85(3) 1.97(4) 2.674(5) 139(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
C1 C2 C3 C4 -1.1(10) . . . . ?
C1 C6 C7 C8 149.9(4) . . . . ?
C1 C6 C7 O3 -24.9(7) . . . . ?
C1 N1 S1 C18 65.1(4) . . . . ?
C1 N1 S1 O1 -52.1(4) . . . . ?
C1 N1 S1 O2 179.7(4) . . . . ?
C2 C1 C6 C5 5.0(7) . . . . ?
C2 C1 C6 C7 -172.6(5) . . . . ?
C2 C1 N1 S1 53.0(6) . . . . ?
C2 C3 C4 C5 3.3(10) . . . . ?
C2 C3 C4 O5 -177.5(6) . . . . ?
C3 C4 C5 C6 -1.3(9) . . . . ?
C3 C4 O5 C17 173.3(7) . . . . ?
C4 C5 C6 C1 -2.9(8) . . . . ?
C4 C5 C6 C7 174.8(5) . . . . ?
C5 C4 O5 C17 -7.6(10) . . . . ?
C5 C6 C7 C8 -27.7(7) . . . . ?
C5 C6 C7 O3 157.5(5) . . . . ?
C6 C1 C2 C3 -3.1(9) . . . . ?
C6 C1 N1 S1 -130.2(4) . . . . ?
C6 C7 C8 C9 -76.4(5) . . . . ?
C6 C7 C8 O4 161.5(4) . . . . ?
C7 C8 C9 C10 -161.3(4) . . . . ?
C7 C8 C9 C11A 80(2) . . . . ?
C7 C8 C9 C11 73.2(5) . . . . ?
C8 C9 C10 N2 174.9(4) . . . . ?
C8 C9 C11A C12A 75(4) . . . . ?
C8 C9 C11A C16A -113(3) . . . . ?
C8 C9 C11 C12 72.4(6) . . . . ?
C8 C9 C11 C16 -103.6(4) . . . . ?
C9 C10 N2 O6 -28.5(7) . . . . ?
C9 C10 N2 O7 156.2(5) . . . . ?
C9 C11A C12A C13A 172(6) . . . . ?
C9 C11A C16A C15A -172(5) . . . . ?
C10 C9 C11A C12A -42(4) . . . . ?
C10 C9 C11A C16A 130(3) . . . . ?
C10 C9 C11 C12 -50.9(6) . . . . ?
C10 C9 C11 C16 133.1(4) . . . . ?
C11A C9 C10 N2 -70(2) . . . . ?
C11A C12A C13A C14A 0.0 . . . . ?
C12A C11A C16A C15A 0.0 . . . . ?
C12A C13A C14A C15A 0.0 . . . . ?
C13A C14A C15A C16A 0.0 . . . . ?
C13A C14A C15A Cl1A 172(4) . . . . ?
C14A C15A C16A C11A 0.0 . . . . ?
C16A C11A C12A C13A 0.0 . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
C13 C12 C11 C9 -176.0(6) . . . . ?
C13 C12 C11 C16 0.0 . . . . ?
C13 C14 C15 C16 0.0 . . . . ?
C14 C15 C16 C11 0.0 . . . . ?
C15 C16 C11 C9 176.0(6) . . . . ?
C15 C16 C11 C12 0.0 . . . . ?
C11 C9 C10 N2 -58.2(5) . . . . ?
C11 C12 C13 C14 0.0 . . . . ?
C11 C12 C13 Cl1 -178.3(4) . . . . ?
C18 C19 C20 C21 -0.9(8) . . . . ?
C19 C18 C23 C22 0.9(7) . . . . ?
C19 C18 S1 N1 -123.8(4) . . . . ?
C19 C18 S1 O1 -6.1(4) . . . . ?
C19 C18 S1 O2 124.6(4) . . . . ?
C19 C20 C21 C22 1.1(8) . . . . ?
C19 C20 C21 C24 -177.8(5) . . . . ?
C20 C21 C22 C23 -0.3(8) . . . . ?
C21 C22 C23 C18 -0.7(7) . . . . ?
C23 C18 C19 C20 -0.1(7) . . . . ?
C23 C18 S1 N1 57.7(4) . . . . ?
C23 C18 S1 O1 175.4(4) . . . . ?
C23 C18 S1 O2 -53.9(4) . . . . ?
C24 C21 C22 C23 178.7(5) . . . . ?
Cl1 C13 C14 C15 178.3(4) . . . . ?
Cl1A C15A C16A C11A -173(4) . . . . ?
N1 C1 C2 C3 173.7(5) . . . . ?
N1 C1 C6 C5 -171.8(4) . . . . ?
N1 C1 C6 C7 10.6(7) . . . . ?
O3 C7 C8 C9 98.7(5) . . . . ?
O3 C7 C8 O4 -23.4(6) . . . . ?
O4 C8 C9 C10 -40.6(5) . . . . ?
O4 C8 C9 C11A -159(2) . . . . ?
O4 C8 C9 C11 -166.1(4) . . . . ?
O5 C4 C5 C6 179.6(5) . . . . ?
S1 C18 C19 C20 -178.7(4) . . . . ?
S1 C18 C23 C22 179.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.194
_oxdiff_exptl_absorpt_empirical_full_min 0.894
