# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_202407255_auto
_database_code_depnum_ccdc_archive 'CCDC 2382370'
loop_
_audit_author_name
_audit_author_address
zhyy-CN
;university of chinese academy of science
China
;
_audit_update_record             
;
2024-09-06 deposited with the CCDC.	2024-12-16 downloaded from the CCDC.
;
_audit_creation_date             2024-07-09
_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         'C21 H19 N3 O2 S'
_chemical_formula_sum            'C21 H19 N3 O2 S'
_chemical_formula_weight         377.45
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H2N2O4S1
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                   7.3145(2)
_cell_length_b                   12.7720(5)
_cell_length_c                   20.9814(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1960.10(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3298
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8610
_cell_measurement_theta_min      4.0480
_shelx_estimated_absorpt_T_max   0.854
_shelx_estimated_absorpt_T_min   0.780
_exptl_absorpt_coefficient_mu    1.632
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.102a (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    1.279
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10719
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.282
_diffrn_reflns_theta_min         4.052
_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 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -59.00  -2.00   1.00    1.00    --  -33.50  77.00 -60.00   57
  2  ω   -101.00 -73.00   1.00    1.00    --  -33.50 178.00-150.00   28
  3  ω    -36.00  30.00   1.00    1.00    --  -33.50  57.00-150.00   66
  4  ω     18.00  50.00   1.00    1.00    --   36.47  57.00 -60.00   32
  5  ω     -2.00  24.00   1.00    1.00    --   36.47  95.00  -3.31   26
  6  ω      9.00  38.00   1.00    1.00    --   36.47  74.00-178.30   29
  7  ω     -2.00  23.00   1.00    1.00    --   36.47  95.00 111.09   25
  8  ω      2.00  28.00   1.00    1.00    --   36.47  92.00-101.80   26
  9  ω     67.00 103.00   1.00    1.00    --   36.47  57.00 -90.00   36
 10  ω     54.00 104.00   1.00    1.00    --   36.47  57.00 -60.00   50
 11  ω    121.00 146.00   1.00    6.00    --  108.00 178.00-150.00   25
 12  ω     44.00 119.00   1.00    6.00    --  108.00 -61.00 -30.00   75
 13  ω    143.00 174.00   1.00    6.00    --  108.00  61.00 -90.00   31
 14  ω    140.00 173.00   1.00    6.00    --  108.00 111.00-120.00   33
 15  ω     97.00 140.00   1.00    6.00    --  108.00  45.00 -90.00   43
 16  ω     61.00 102.00   1.00    6.00    --  108.00 178.00-150.00   41
 17  ω     47.00  74.00   1.00    6.00    --  108.00 -45.00  90.00   27
 18  ω     85.00 113.00   1.00    6.00    --  108.00  30.00 -30.00   28
 19  ω     66.00  92.00   1.00    6.00    --  108.00 -94.00 -30.00   26
 20  ω     65.00 127.00   1.00    6.00    --  108.00 -61.00  90.00   62
 21  ω     38.00 100.00   1.00    6.00    --  108.00 -45.00-180.00   62
 22  ω    145.00 177.00   1.00    6.00    --  108.00  30.00 -30.00   32
 23  ω     67.00 108.00   1.00    6.00    --  108.00-111.00 -30.00   41
 24  ω     43.00  90.00   1.00    6.00    --  108.00 -30.00 -30.00   47
 25  ω     94.00 131.00   1.00    6.00    --  108.00 -30.00 -30.00   37
 26  ω    112.00 138.00   1.00    6.00    --  108.00  61.00 -90.00   26
 27  ω    117.00 144.00   1.00    6.00    --  108.00 111.00  30.00   27
 28  ω    122.00 148.00   1.00    6.00    --  108.00  45.00-120.00   26
 29  ω    107.00 133.00   1.00    6.00    --  108.00 111.00   0.00   26
 30  ω     92.00 118.00   1.00    6.00    --  108.00 -45.00  90.00   26
 31  ω     92.00 126.00   1.00    6.00    --  108.00 -45.00 -30.00   34
 32  ω     42.00  68.00   1.00    6.00    --  108.00 -45.00 -30.00   26
;
_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      -0.0567708000
_diffrn_orient_matrix_UB_12      -0.0847664000
_diffrn_orient_matrix_UB_13      -0.0483940000
_diffrn_orient_matrix_UB_21      -0.0326427000
_diffrn_orient_matrix_UB_22      -0.0775697000
_diffrn_orient_matrix_UB_23      0.0550326000
_diffrn_orient_matrix_UB_31      -0.2001657000
_diffrn_orient_matrix_UB_32      0.0366667000
_diffrn_orient_matrix_UB_33      0.0047072000
_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         0.731
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3277
_reflns_number_total             3772
_reflns_odcompleteness_completeness 98.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (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         0.144
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 1138 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.012(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     253
_refine_ls_number_reflns         3772
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0459
_refine_ls_restrained_S_all      1.037
_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)+(0.0560P)²+0.0315P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1181
_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:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C16(H16), C17(H17), C19(H19),
 C20(H20)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_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
S1 S 0.71496(12) 0.58857(8) 0.41393(4) 0.0608(2) Uani 1 1 d . . . . .
O1 O 0.8322(4) 0.5125(3) 0.38625(14) 0.0798(9) Uani 1 1 d . . . . .
O2 O 0.7842(5) 0.6629(3) 0.45864(14) 0.0827(9) Uani 1 1 d . . . . .
N1 N 0.6319(4) 0.6575(2) 0.35377(13) 0.0550(6) Uani 1 1 d . . . . .
N2 N 0.3995(5) 0.8078(3) 0.20828(18) 0.0745(9) Uani 1 1 d . . . . .
N3 N 0.3266(7) 0.4771(3) 0.1857(2) 0.0913(13) Uani 1 1 d . . . . .
C1 C 0.5096(6) 0.7447(3) 0.36943(18) 0.0620(9) Uani 1 1 d . . . . .
H1A H 0.5398 0.8037 0.3423 0.074 Uiso 1 1 calc R . . . .
H1B H 0.5319 0.7657 0.4132 0.074 Uiso 1 1 calc R . . . .
C2 C 0.3102(6) 0.7204(3) 0.36193(16) 0.0596(8) Uani 1 1 d . . . . .
C3 C 0.2704(5) 0.6279(3) 0.31986(16) 0.0573(7) Uani 1 1 d . . . . .
H3A H 0.1477 0.6334 0.3026 0.069 Uiso 1 1 calc R . . . .
H3B H 0.2784 0.5637 0.3444 0.069 Uiso 1 1 calc R . . . .
C4 C 0.4106(5) 0.6261(3) 0.26539(15) 0.0511(7) Uani 1 1 d . . . . .
C5 C 0.6095(5) 0.6039(3) 0.29251(15) 0.0517(7) Uani 1 1 d . . . . .
H5 H 0.6191 0.5285 0.3004 0.062 Uiso 1 1 calc R . . . .
C6 C 0.7533(5) 0.6325(3) 0.24353(16) 0.0621(9) Uani 1 1 d . . . . .
C7 C 0.8022(7) 0.5580(5) 0.1979(2) 0.0845(13) Uani 1 1 d . . . . .
H7 H 0.7565 0.4901 0.2004 0.101 Uiso 1 1 calc R . . . .
C8 C 0.9189(8) 0.5859(8) 0.1490(3) 0.116(2) Uani 1 1 d . . . . .
H8 H 0.9492 0.5370 0.1180 0.139 Uiso 1 1 calc R . . . .
C9 C 0.9907(8) 0.6850(8) 0.1458(3) 0.119(3) Uani 1 1 d . . . . .
H9 H 1.0694 0.7029 0.1127 0.143 Uiso 1 1 calc R . . . .
C10 C 0.9466(6) 0.7571(6) 0.1910(3) 0.0982(19) Uani 1 1 d . . . . .
H10 H 0.9960 0.8241 0.1887 0.118 Uiso 1 1 calc R . . . .
C11 C 0.8279(5) 0.7317(4) 0.2408(2) 0.0742(11) Uani 1 1 d . . . . .
H11 H 0.7994 0.7810 0.2718 0.089 Uiso 1 1 calc R . . . .
C12 C 0.1806(8) 0.7783(5) 0.3870(3) 0.0885(14) Uani 1 1 d . . . . .
H12A H 0.217(8) 0.836(4) 0.415(3) 0.098(17) Uiso 1 1 d . . . . .
H12B H 0.047(8) 0.764(5) 0.379(3) 0.091(16) Uiso 1 1 d . . . . .
C13 C 0.4051(5) 0.7279(3) 0.23126(16) 0.0550(7) Uani 1 1 d . . . . .
C14 C 0.3657(5) 0.5424(3) 0.21953(18) 0.0632(9) Uani 1 1 d . . . . .
C15 C 0.5265(5) 0.5256(3) 0.44969(14) 0.0544(7) Uani 1 1 d . . . . .
C16 C 0.4796(7) 0.4250(3) 0.43084(18) 0.0687(10) Uani 1 1 d . . . . .
H16 H 0.5528 0.3883 0.4023 0.082 Uiso 1 1 calc R . . . .
C17 C 0.3239(7) 0.3803(3) 0.4549(2) 0.0769(12) Uani 1 1 d . . . . .
H17 H 0.2922 0.3130 0.4422 0.092 Uiso 1 1 calc R . . . .
C18 C 0.2124(7) 0.4329(3) 0.4977(2) 0.0743(10) Uani 1 1 d . . . . .
C19 C 0.2622(7) 0.5326(3) 0.51602(18) 0.0709(10) Uani 1 1 d . . . . .
H19 H 0.1892 0.5691 0.5447 0.085 Uiso 1 1 calc R . . . .
C20 C 0.4190(6) 0.5793(3) 0.49240(15) 0.0615(8) Uani 1 1 d . . . . .
H20 H 0.4514 0.6465 0.5053 0.074 Uiso 1 1 calc R . . . .
C21 C 0.0385(9) 0.3836(5) 0.5231(3) 0.112(2) Uani 1 1 d . . . . .
H21A H 0.0270 0.3987 0.5678 0.168 Uiso 1 1 calc GR . . . .
H21B H 0.0434 0.3091 0.5170 0.168 Uiso 1 1 calc GR . . . .
H21C H -0.0649 0.4116 0.5007 0.168 Uiso 1 1 calc GR . . . .


_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 1.420(3) . ?
S1 O2 1.428(3) . ?
S1 N1 1.654(3) . ?
S1 C15 1.763(4) . ?
N1 C1 1.466(5) . ?
N1 C5 1.465(4) . ?
N2 C13 1.129(5) . ?
N3 C14 1.132(6) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.499(6) . ?
C2 C3 1.504(5) . ?
C2 C12 1.312(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.536(5) . ?
C4 C5 1.587(4) . ?
C4 C13 1.486(5) . ?
C4 C14 1.475(5) . ?
C5 H5 0.9800 . ?
C5 C6 1.515(5) . ?
C6 C7 1.396(6) . ?
C6 C11 1.381(7) . ?
C7 H7 0.9300 . ?
C7 C8 1.381(8) . ?
C8 H8 0.9300 . ?
C8 C9 1.372(11) . ?
C9 H9 0.9300 . ?
C9 C10 1.361(10) . ?
C10 H10 0.9300 . ?
C10 C11 1.397(6) . ?
C11 H11 0.9300 . ?
C12 H12A 0.97(6) . ?
C12 H12B 1.01(6) . ?
C15 C16 1.388(5) . ?
C15 C20 1.376(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.370(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.386(7) . ?
C18 C19 1.379(6) . ?
C18 C21 1.516(8) . ?
C19 H19 0.9300 . ?
C19 C20 1.385(6) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
O1 S1 O2 120.6(2) . . ?
O1 S1 N1 105.86(17) . . ?
O1 S1 C15 109.5(2) . . ?
O2 S1 N1 106.13(19) . . ?
O2 S1 C15 107.54(18) . . ?
N1 S1 C15 106.27(16) . . ?
C1 N1 S1 117.2(2) . . ?
C5 N1 S1 117.5(2) . . ?
C5 N1 C1 118.9(3) . . ?
N1 C1 H1A 108.7 . . ?
N1 C1 H1B 108.7 . . ?
N1 C1 C2 114.4(3) . . ?
H1A C1 H1B 107.6 . . ?
C2 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
C1 C2 C3 114.4(3) . . ?
C12 C2 C1 123.0(4) . . ?
C12 C2 C3 122.6(5) . . ?
C2 C3 H3A 110.0 . . ?
C2 C3 H3B 110.0 . . ?
C2 C3 C4 108.6(3) . . ?
H3A C3 H3B 108.3 . . ?
C4 C3 H3A 110.0 . . ?
C4 C3 H3B 110.0 . . ?
C3 C4 C5 110.4(3) . . ?
C13 C4 C3 109.1(3) . . ?
C13 C4 C5 110.7(3) . . ?
C14 C4 C3 110.4(3) . . ?
C14 C4 C5 108.0(3) . . ?
C14 C4 C13 108.3(3) . . ?
N1 C5 C4 109.5(3) . . ?
N1 C5 H5 107.6 . . ?
N1 C5 C6 113.9(3) . . ?
C4 C5 H5 107.6 . . ?
C6 C5 C4 110.5(3) . . ?
C6 C5 H5 107.6 . . ?
C7 C6 C5 118.6(4) . . ?
C11 C6 C5 121.6(4) . . ?
C11 C6 C7 119.7(4) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 C6 119.4(6) . . ?
C8 C7 H7 120.3 . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.8(6) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.9(5) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.8(6) . . ?
C11 C10 H10 119.6 . . ?
C6 C11 C10 119.3(5) . . ?
C6 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C2 C12 H12A 118(4) . . ?
C2 C12 H12B 122(3) . . ?
H12A C12 H12B 120(5) . . ?
N2 C13 C4 176.4(4) . . ?
N3 C14 C4 177.6(5) . . ?
C16 C15 S1 119.6(3) . . ?
C20 C15 S1 119.8(3) . . ?
C20 C15 C16 120.4(4) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 C15 119.1(4) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 H17 119.1 . . ?
C16 C17 C18 121.8(4) . . ?
C18 C17 H17 119.1 . . ?
C17 C18 C21 121.4(5) . . ?
C19 C18 C17 118.2(4) . . ?
C19 C18 C21 120.5(5) . . ?
C18 C19 H19 119.4 . . ?
C18 C19 C20 121.1(4) . . ?
C20 C19 H19 119.4 . . ?
C15 C20 C19 119.5(4) . . ?
C15 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C1 C2 -99.9(3) . . . . ?
S1 N1 C5 C4 131.2(2) . . . . ?
S1 N1 C5 C6 -104.5(3) . . . . ?
S1 C15 C16 C17 -174.4(3) . . . . ?
S1 C15 C20 C19 174.3(3) . . . . ?
O1 S1 N1 C1 -178.1(3) . . . . ?
O1 S1 N1 C5 30.2(3) . . . . ?
O1 S1 C15 C16 -20.8(3) . . . . ?
O1 S1 C15 C20 164.2(3) . . . . ?
O2 S1 N1 C1 -48.8(3) . . . . ?
O2 S1 N1 C5 159.5(3) . . . . ?
O2 S1 C15 C16 -153.6(3) . . . . ?
O2 S1 C15 C20 31.4(3) . . . . ?
N1 S1 C15 C16 93.1(3) . . . . ?
N1 S1 C15 C20 -81.9(3) . . . . ?
N1 C1 C2 C3 -19.7(4) . . . . ?
N1 C1 C2 C12 163.9(4) . . . . ?
N1 C5 C6 C7 150.3(3) . . . . ?
N1 C5 C6 C11 -33.7(5) . . . . ?
C1 N1 C5 C4 -20.0(4) . . . . ?
C1 N1 C5 C6 104.3(4) . . . . ?
C1 C2 C3 C4 -35.8(4) . . . . ?
C2 C3 C4 C5 66.1(3) . . . . ?
C2 C3 C4 C13 -55.7(4) . . . . ?
C2 C3 C4 C14 -174.6(3) . . . . ?
C3 C4 C5 N1 -37.5(4) . . . . ?
C3 C4 C5 C6 -163.7(3) . . . . ?
C4 C5 C6 C7 -86.0(4) . . . . ?
C4 C5 C6 C11 90.0(4) . . . . ?
C5 N1 C1 C2 51.5(4) . . . . ?
C5 C6 C7 C8 173.4(4) . . . . ?
C5 C6 C11 C10 -173.8(3) . . . . ?
C6 C7 C8 C9 1.7(8) . . . . ?
C7 C6 C11 C10 2.2(6) . . . . ?
C7 C8 C9 C10 -0.2(9) . . . . ?
C8 C9 C10 C11 -0.3(8) . . . . ?
C9 C10 C11 C6 -0.7(7) . . . . ?
C11 C6 C7 C8 -2.7(6) . . . . ?
C12 C2 C3 C4 140.6(4) . . . . ?
C13 C4 C5 N1 83.4(3) . . . . ?
C13 C4 C5 C6 -42.8(4) . . . . ?
C14 C4 C5 N1 -158.2(3) . . . . ?
C14 C4 C5 C6 75.6(4) . . . . ?
C15 S1 N1 C1 65.5(3) . . . . ?
C15 S1 N1 C5 -86.2(3) . . . . ?
C15 C16 C17 C18 -0.2(6) . . . . ?
C16 C15 C20 C19 -0.7(5) . . . . ?
C16 C17 C18 C19 -0.1(7) . . . . ?
C16 C17 C18 C21 178.8(5) . . . . ?
C17 C18 C19 C20 0.0(6) . . . . ?
C18 C19 C20 C15 0.4(6) . . . . ?
C20 C15 C16 C17 0.6(6) . . . . ?
C21 C18 C19 C20 -178.9(5) . . . . ?

_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 1.146
_oxdiff_exptl_absorpt_empirical_full_min 0.930
####################################################################### 
# 
# 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_20240139_auto
_database_code_depnum_ccdc_archive 'CCDC 2382372'
loop_
_audit_author_name
_audit_author_address
zhyy-BBT
;university of chinese academy of science
China
;
_audit_update_record             
;
2024-09-06 deposited with the CCDC.	2024-12-16 downloaded from the CCDC.
;
_audit_creation_date             2024-01-23
_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 H24 Br N3 O5 S'
_chemical_formula_sum            'C24 H24 Br N3 O5 S'
_chemical_formula_weight         546.43
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H20N4O4S1Br1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   7.7240(3)
_cell_length_b                   13.7301(5)
_cell_length_c                   23.5210(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2494.46(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3121
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.6170
_cell_measurement_theta_min      3.7130
_shelx_estimated_absorpt_T_max   0.730
_shelx_estimated_absorpt_T_min   0.632
_exptl_absorpt_coefficient_mu    3.365
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51111
_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    1.455
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.439
_diffrn_reflns_theta_min         3.728
_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 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   -102.00 -15.00   1.00    1.00    --  -33.50 -57.00  60.00   87
  2  ω    -52.00  35.00   1.00    1.00    --  -33.50  57.00-150.00   87
  3  ω   -108.00 -35.00   1.00    1.00    --  -33.50 178.00-150.00   73
  4  ω   -104.00 -14.00   1.00    1.00    --  -33.50 -37.00  90.00   90
  5  ω    107.00 136.00   1.00    7.50    --  108.00  77.00  90.00   29
  6  ω    112.00 171.00   1.00    7.50    --  108.00  77.00-180.00   59
  7  ω     96.00 177.00   1.00    7.50    --  108.00  45.00 -60.00   81
  8  ω    111.00 163.00   1.00    7.50    --  108.00 111.00  30.00   52
  9  ω    143.00 169.00   1.00    7.50    --  108.00 111.00 -60.00   26
 10  ω     51.00 107.00   1.00    7.50    --  108.00-111.00  90.00   56
 11  ω    101.00 169.00   1.00    7.50    --  108.00  77.00 120.00   68
 12  ω    101.00 141.00   1.00    7.50    --  108.00  77.00 -30.00   40
 13  ω     57.00 107.00   1.00    7.50    --  108.00-111.00 150.00   50
;
_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      -0.0473575000
_diffrn_orient_matrix_UB_12      0.0287857000
_diffrn_orient_matrix_UB_13      -0.0613495000
_diffrn_orient_matrix_UB_21      0.1546114000
_diffrn_orient_matrix_UB_22      -0.0596828000
_diffrn_orient_matrix_UB_23      -0.0223538000
_diffrn_orient_matrix_UB_31      -0.1167477000
_diffrn_orient_matrix_UB_32      -0.0906090000
_diffrn_orient_matrix_UB_33      -0.0047911000
_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         0.723
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                3776
_reflns_number_total             4667
_reflns_odcompleteness_completeness 99.92
_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         0.445
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
 Flack x determined using 1260 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(3)
_refine_ls_extinction_coef       0.0010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4667
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0563
_refine_ls_restrained_S_all      1.036
_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)+(0.0796P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1456
_refine_ls_wR_factor_ref         0.1581
_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:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C19(H19), C20(H20), C22(H22), C23(H23)
2.d X=CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.e Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_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
Br1 Br 0.96499(16) 0.47798(11) 0.54707(7) 0.1429(7) Uani 1 1 d . . . . .
S1 S 0.6078(2) 0.62392(10) 0.83781(7) 0.0623(4) Uani 1 1 d . . . . .
O1 O 0.7919(6) 0.6208(4) 0.8300(2) 0.0777(13) Uani 1 1 d . . . . .
O2 O 0.5181(9) 0.5377(3) 0.8528(2) 0.0901(16) Uani 1 1 d . . . . .
O3 O 0.7462(7) 0.9327(3) 0.7523(2) 0.0746(12) Uani 1 1 d . . . . .
O4 O 0.3168(6) 0.7605(4) 0.6564(2) 0.0789(13) Uani 1 1 d . . . . .
O5 O 0.7904(11) 0.8702(7) 0.5652(3) 0.129(3) Uani 1 1 d . . . . .
N1 N 0.5279(6) 0.6632(3) 0.7780(2) 0.0575(11) Uani 1 1 d . . . . .
N2 N 0.7787(7) 0.8939(4) 0.6595(3) 0.0678(13) Uani 1 1 d . . . . .
N3 N 0.5541(8) 0.8131(4) 0.6111(2) 0.0720(14) Uani 1 1 d . . . . .
C1 C 0.8916(8) 0.6728(5) 0.6782(3) 0.0687(16) Uani 1 1 d . . . . .
H1 H 0.9569 0.7200 0.6967 0.082 Uiso 1 1 calc R . . . .
C2 C 0.9661(9) 0.6198(6) 0.6348(4) 0.083(2) Uani 1 1 d . . . . .
H2 H 1.0801 0.6309 0.6239 0.099 Uiso 1 1 calc R . . . .
C3 C 0.8690(10) 0.5515(5) 0.6087(4) 0.079(2) Uani 1 1 d . . . . .
C4 C 0.7015(9) 0.5320(5) 0.6240(4) 0.0761(18) Uani 1 1 d . . . . .
H4 H 0.6383 0.4839 0.6054 0.091 Uiso 1 1 calc R . . . .
C5 C 0.6290(8) 0.5848(4) 0.6673(3) 0.0661(15) Uani 1 1 d . . . . .
H5 H 0.5158 0.5717 0.6784 0.079 Uiso 1 1 calc R . . . .
C6 C 0.7210(7) 0.6573(4) 0.6951(3) 0.0555(12) Uani 1 1 d . . . . .
C7 C 0.6415(7) 0.7201(4) 0.7398(2) 0.0527(12) Uani 1 1 d . . . . .
H7 H 0.7374 0.7437 0.7634 0.063 Uiso 1 1 calc R . . . .
C8 C 0.5467(7) 0.8150(4) 0.7157(3) 0.0530(12) Uani 1 1 d . . . . .
C9 C 0.4150(8) 0.8528(4) 0.7595(3) 0.0610(14) Uani 1 1 d . . . . .
H9A H 0.4778 0.8765 0.7924 0.073 Uiso 1 1 calc R . . . .
H9B H 0.3539 0.9077 0.7430 0.073 Uiso 1 1 calc R . . . .
C10 C 0.2836(8) 0.7790(4) 0.7791(3) 0.0614(14) Uani 1 1 d . . . . .
C11 C 0.3376(8) 0.6744(4) 0.7740(3) 0.0610(13) Uani 1 1 d . . . . .
H11A H 0.2829 0.6368 0.8039 0.073 Uiso 1 1 calc R . . . .
H11B H 0.2982 0.6488 0.7378 0.073 Uiso 1 1 calc R . . . .
C12 C 0.1324(9) 0.8033(6) 0.8010(4) 0.0801(19) Uani 1 1 d . . . . .
H12A H 0.0569 0.7551 0.8135 0.096 Uiso 1 1 calc R . . . .
H12B H 0.1013 0.8685 0.8038 0.096 Uiso 1 1 calc R . . . .
C13 C 0.6962(8) 0.8881(4) 0.7112(3) 0.0615(14) Uani 1 1 d . . . . .
C14 C 0.4604(8) 0.7944(4) 0.6596(3) 0.0613(13) Uani 1 1 d . . . . .
C15 C 0.7124(11) 0.8579(6) 0.6094(3) 0.0806(19) Uani 1 1 d . . . . .
C16 C 0.9418(10) 0.9489(6) 0.6577(4) 0.094(2) Uani 1 1 d . . . . .
H16A H 0.9180 1.0156 0.6482 0.141 Uiso 1 1 calc GR . . . .
H16B H 1.0168 0.9212 0.6294 0.141 Uiso 1 1 calc GR . . . .
H16C H 0.9972 0.9459 0.6942 0.141 Uiso 1 1 calc GR . . . .
C17 C 0.4769(17) 0.7825(10) 0.5559(4) 0.125(4) Uani 1 1 d . . . . .
H17A H 0.5161 0.7181 0.5466 0.187 Uiso 1 1 calc GR . . . .
H17B H 0.5119 0.8270 0.5266 0.187 Uiso 1 1 calc GR . . . .
H17C H 0.3530 0.7826 0.5590 0.187 Uiso 1 1 calc GR . . . .
C18 C 0.5623(8) 0.7118(4) 0.8905(3) 0.0580(13) Uani 1 1 d . . . . .
C19 C 0.6542(9) 0.7983(5) 0.8914(3) 0.0677(15) Uani 1 1 d . . . . .
H19 H 0.7398 0.8108 0.8646 0.081 Uiso 1 1 calc R . . . .
C20 C 0.6153(11) 0.8656(6) 0.9333(3) 0.0811(19) Uani 1 1 d . . . . .
H20 H 0.6749 0.9245 0.9339 0.097 Uiso 1 1 calc R . . . .
C21 C 0.4907(11) 0.8481(7) 0.9743(3) 0.088(2) Uani 1 1 d . . . . .
C22 C 0.4027(12) 0.7624(8) 0.9714(3) 0.097(3) Uani 1 1 d . . . . .
H22 H 0.3182 0.7492 0.9985 0.116 Uiso 1 1 calc R . . . .
C23 C 0.4341(11) 0.6961(6) 0.9304(3) 0.082(2) Uani 1 1 d . . . . .
H23 H 0.3689 0.6392 0.9289 0.098 Uiso 1 1 calc R . . . .
C24 C 0.466(2) 0.9242(11) 1.0204(5) 0.140(5) Uani 1 1 d . . . . .
H24A H 0.5764 0.9523 1.0300 0.210 Uiso 1 1 calc GR . . . .
H24B H 0.4172 0.8942 1.0535 0.210 Uiso 1 1 calc GR . . . .
H24C H 0.3900 0.9743 1.0069 0.210 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C3 1.916(7) . ?
S1 O1 1.435(5) . ?
S1 O2 1.416(5) . ?
S1 N1 1.627(5) . ?
S1 C18 1.765(7) . ?
O3 C13 1.208(8) . ?
O4 C14 1.205(8) . ?
O5 C15 1.212(11) . ?
N1 C7 1.479(8) . ?
N1 C11 1.481(8) . ?
N2 C13 1.375(9) . ?
N2 C15 1.377(11) . ?
N2 C16 1.470(9) . ?
N3 C14 1.375(9) . ?
N3 C15 1.369(10) . ?
N3 C17 1.489(11) . ?
C1 H1 0.9300 . ?
C1 C2 1.379(11) . ?
C1 C6 1.392(9) . ?
C2 H2 0.9300 . ?
C2 C3 1.349(11) . ?
C3 C4 1.370(11) . ?
C4 H4 0.9300 . ?
C4 C5 1.370(10) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(8) . ?
C6 C7 1.494(8) . ?
C7 H7 0.9800 . ?
C7 C8 1.598(7) . ?
C8 C9 1.537(8) . ?
C8 C13 1.534(8) . ?
C8 C14 1.506(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.506(9) . ?
C10 C11 1.501(8) . ?
C10 C12 1.319(10) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9300 . ?
C12 H12B 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.383(9) . ?
C18 C23 1.380(10) . ?
C19 H19 0.9300 . ?
C19 C20 1.384(11) . ?
C20 H20 0.9300 . ?
C20 C21 1.383(12) . ?
C21 C22 1.361(14) . ?
C21 C24 1.518(13) . ?
C22 H22 0.9300 . ?
C22 C23 1.349(13) . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
O1 S1 N1 105.9(3) . . ?
O1 S1 C18 107.9(3) . . ?
O2 S1 O1 119.5(4) . . ?
O2 S1 N1 107.9(3) . . ?
O2 S1 C18 107.4(3) . . ?
N1 S1 C18 107.7(3) . . ?
C7 N1 S1 118.4(4) . . ?
C7 N1 C11 119.7(5) . . ?
C11 N1 S1 117.8(4) . . ?
C13 N2 C15 124.3(6) . . ?
C13 N2 C16 116.9(7) . . ?
C15 N2 C16 118.6(7) . . ?
C14 N3 C17 117.3(7) . . ?
C15 N3 C14 125.4(6) . . ?
C15 N3 C17 117.3(7) . . ?
C2 C1 H1 119.2 . . ?
C2 C1 C6 121.7(6) . . ?
C6 C1 H1 119.2 . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.2(7) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 Br1 119.7(6) . . ?
C2 C3 C4 122.8(7) . . ?
C4 C3 Br1 117.5(6) . . ?
C3 C4 H4 120.7 . . ?
C3 C4 C5 118.6(6) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.4(6) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C7 120.1(5) . . ?
C5 C6 C1 117.5(6) . . ?
C5 C6 C7 122.4(5) . . ?
N1 C7 C6 111.5(4) . . ?
N1 C7 H7 106.2 . . ?
N1 C7 C8 112.0(4) . . ?
C6 C7 H7 106.2 . . ?
C6 C7 C8 114.2(5) . . ?
C8 C7 H7 106.2 . . ?
C9 C8 C7 109.9(5) . . ?
C13 C8 C7 102.3(4) . . ?
C13 C8 C9 108.9(5) . . ?
C14 C8 C7 111.2(4) . . ?
C14 C8 C9 110.9(5) . . ?
C14 C8 C13 113.3(5) . . ?
C8 C9 H9A 108.5 . . ?
C8 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
C10 C9 C8 115.1(5) . . ?
C10 C9 H9A 108.5 . . ?
C10 C9 H9B 108.5 . . ?
C11 C10 C9 115.6(5) . . ?
C12 C10 C9 123.1(6) . . ?
C12 C10 C11 121.3(6) . . ?
N1 C11 C10 111.7(5) . . ?
N1 C11 H11A 109.3 . . ?
N1 C11 H11B 109.3 . . ?
C10 C11 H11A 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C10 C12 H12A 120.0 . . ?
C10 C12 H12B 120.0 . . ?
H12A C12 H12B 120.0 . . ?
O3 C13 N2 122.0(6) . . ?
O3 C13 C8 121.1(6) . . ?
N2 C13 C8 116.6(5) . . ?
O4 C14 N3 120.4(6) . . ?
O4 C14 C8 122.3(6) . . ?
N3 C14 C8 117.3(5) . . ?
O5 C15 N2 119.9(8) . . ?
O5 C15 N3 122.2(8) . . ?
N3 C15 N2 117.9(7) . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
N3 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 S1 119.7(5) . . ?
C23 C18 S1 120.8(5) . . ?
C23 C18 C19 119.4(7) . . ?
C18 C19 H19 120.9 . . ?
C18 C19 C20 118.3(7) . . ?
C20 C19 H19 120.9 . . ?
C19 C20 H20 119.0 . . ?
C21 C20 C19 122.0(7) . . ?
C21 C20 H20 119.0 . . ?
C20 C21 C24 117.7(10) . . ?
C22 C21 C20 117.6(8) . . ?
C22 C21 C24 124.7(10) . . ?
C21 C22 H22 119.0 . . ?
C23 C22 C21 122.0(8) . . ?
C23 C22 H22 119.0 . . ?
C18 C23 H23 119.7 . . ?
C22 C23 C18 120.6(7) . . ?
C22 C23 H23 119.7 . . ?
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 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C3 C4 C5 -178.9(6) . . . . ?
S1 N1 C7 C6 96.1(5) . . . . ?
S1 N1 C7 C8 -134.6(4) . . . . ?
S1 N1 C11 C10 102.7(5) . . . . ?
S1 C18 C19 C20 180.0(5) . . . . ?
S1 C18 C23 C22 178.4(7) . . . . ?
O1 S1 N1 C7 -22.7(5) . . . . ?
O1 S1 N1 C11 -179.6(4) . . . . ?
O1 S1 C18 C19 39.9(6) . . . . ?
O1 S1 C18 C23 -141.1(6) . . . . ?
O2 S1 N1 C7 -151.7(4) . . . . ?
O2 S1 N1 C11 51.3(5) . . . . ?
O2 S1 C18 C19 170.0(5) . . . . ?
O2 S1 C18 C23 -11.0(7) . . . . ?
N1 S1 C18 C19 -74.0(6) . . . . ?
N1 S1 C18 C23 104.9(6) . . . . ?
N1 C7 C8 C9 30.9(6) . . . . ?
N1 C7 C8 C13 146.4(5) . . . . ?
N1 C7 C8 C14 -92.4(6) . . . . ?
C1 C2 C3 Br1 178.6(6) . . . . ?
C1 C2 C3 C4 -0.9(14) . . . . ?
C1 C6 C7 N1 -141.6(6) . . . . ?
C1 C6 C7 C8 90.2(7) . . . . ?
C2 C1 C6 C5 1.4(10) . . . . ?
C2 C1 C6 C7 -176.3(7) . . . . ?
C2 C3 C4 C5 0.7(14) . . . . ?
C3 C4 C5 C6 0.6(12) . . . . ?
C4 C5 C6 C1 -1.6(10) . . . . ?
C4 C5 C6 C7 176.0(6) . . . . ?
C5 C6 C7 N1 40.9(8) . . . . ?
C5 C6 C7 C8 -87.3(7) . . . . ?
C6 C1 C2 C3 -0.2(12) . . . . ?
C6 C7 C8 C9 158.8(5) . . . . ?
C6 C7 C8 C13 -85.7(5) . . . . ?
C6 C7 C8 C14 35.6(7) . . . . ?
C7 N1 C11 C10 -54.0(8) . . . . ?
C7 C8 C9 C10 -54.6(7) . . . . ?
C7 C8 C13 O3 -81.2(7) . . . . ?
C7 C8 C13 N2 93.5(6) . . . . ?
C7 C8 C14 O4 85.4(7) . . . . ?
C7 C8 C14 N3 -92.8(6) . . . . ?
C8 C9 C10 C11 24.3(8) . . . . ?
C8 C9 C10 C12 -157.4(7) . . . . ?
C9 C8 C13 O3 35.1(8) . . . . ?
C9 C8 C13 N2 -150.2(5) . . . . ?
C9 C8 C14 O4 -37.3(8) . . . . ?
C9 C8 C14 N3 144.6(5) . . . . ?
C9 C10 C11 N1 28.2(8) . . . . ?
C11 N1 C7 C6 -107.4(6) . . . . ?
C11 N1 C7 C8 22.0(7) . . . . ?
C12 C10 C11 N1 -150.1(7) . . . . ?
C13 N2 C15 O5 176.6(8) . . . . ?
C13 N2 C15 N3 -0.3(10) . . . . ?
C13 C8 C9 C10 -165.9(5) . . . . ?
C13 C8 C14 O4 -160.1(6) . . . . ?
C13 C8 C14 N3 21.8(7) . . . . ?
C14 N3 C15 O5 178.2(9) . . . . ?
C14 N3 C15 N2 -5.1(11) . . . . ?
C14 C8 C9 C10 68.7(6) . . . . ?
C14 C8 C13 O3 159.0(6) . . . . ?
C14 C8 C13 N2 -26.3(7) . . . . ?
C15 N2 C13 O3 -168.9(7) . . . . ?
C15 N2 C13 C8 16.5(9) . . . . ?
C15 N3 C14 O4 174.9(7) . . . . ?
C15 N3 C14 C8 -6.9(9) . . . . ?
C16 N2 C13 O3 6.2(9) . . . . ?
C16 N2 C13 C8 -168.5(6) . . . . ?
C16 N2 C15 O5 1.6(12) . . . . ?
C16 N2 C15 N3 -175.2(7) . . . . ?
C17 N3 C14 O4 -4.9(10) . . . . ?
C17 N3 C14 C8 173.3(8) . . . . ?
C17 N3 C15 O5 -2.1(13) . . . . ?
C17 N3 C15 N2 174.7(8) . . . . ?
C18 S1 N1 C7 92.6(4) . . . . ?
C18 S1 N1 C11 -64.3(5) . . . . ?
C18 C19 C20 C21 1.1(11) . . . . ?
C19 C18 C23 C22 -2.6(11) . . . . ?
C19 C20 C21 C22 -1.7(12) . . . . ?
C19 C20 C21 C24 176.2(8) . . . . ?
C20 C21 C22 C23 0.0(13) . . . . ?
C21 C22 C23 C18 2.1(14) . . . . ?
C23 C18 C19 C20 1.0(10) . . . . ?
C24 C21 C22 C23 -177.7(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.058
_oxdiff_exptl_absorpt_empirical_full_min 0.731
####################################################################### 
# 
# 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_20220462
_database_code_depnum_ccdc_archive 'CCDC 2382373'
loop_
_audit_author_name
_audit_author_address
zhyy-st
;university of chinese academy of science
China
;
_audit_update_record             
;
2024-09-06 deposited with the CCDC.	2024-12-16 downloaded from the CCDC.
;
_audit_creation_date             2022-04-12
_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         'C21 H18 N2 O4 S'
_chemical_formula_sum            'C21 H18 N2 O4 S'
_chemical_formula_weight         394.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H3O3N1S1
_chemical_oxdiff_usercomment     r
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.6187(3)
_cell_length_b                   9.7369(2)
_cell_length_c                   17.6621(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.931(3)
_cell_angle_gamma                90
_cell_volume                     1921.38(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4489
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8470
_cell_measurement_theta_min      4.0920
_shelx_estimated_absorpt_T_max   0.844
_shelx_estimated_absorpt_T_min   0.767
_exptl_absorpt_coefficient_mu    1.755
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.364
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13206
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.080
_diffrn_reflns_theta_max         67.080
_diffrn_reflns_theta_min         4.096
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -15.00   1.00    1.70    --  -33.50 -57.00  30.00   87
  2  ω   -106.00 -69.00   1.00    1.70    --  -33.50 178.00 -90.00   37
  3  ω    -40.00  35.00   1.00    1.70    --  -33.50  57.00-180.00   75
  4  ω    -60.00 -34.00   1.00    1.70    --  -33.50 178.00 150.00   26
  5  ω    -66.00 -39.00   1.00    1.70    --  -33.50 178.00 -90.00   27
  6  ω      9.00  97.00   1.00    1.70    --   36.47  77.00  90.00   88
  7  ω     -4.00  45.00   1.00    1.70    --   36.47 -57.00  30.00   49
  8  ω     75.00 101.00   1.00    1.70    --   36.47 178.00-150.00   26
  9  ω     57.00  82.00   1.00    1.70    --   36.47 178.00  30.00   25
 10  ω     62.00  88.00   1.00    1.70    --   36.47  37.00  30.00   26
 11  ω     23.00  99.00   1.00    1.70    --   36.47  57.00 -90.00   76
 12  ω     15.00  56.00   1.00    1.70    --   36.47  37.00  30.00   41
 13  ω     -4.00  43.00   1.00    1.70    --   36.47 -99.00-120.00   47
 14  ω     57.00 103.00   1.00    1.70    --   36.47 178.00-120.00   46
 15  ω     47.00  73.00   1.00    1.70    --   36.47 -99.00 150.00   26
 16  ω     79.00 174.00   1.00    7.50    --  108.00   0.00  90.00   95
 17  ω     81.00 112.00   1.00    7.50    --  108.00-111.00 -60.00   31
 18  ω     44.00  74.00   1.00    7.50    --  108.00   0.00  90.00   30
 19  ω     89.00 126.00   1.00    7.50    --  108.00 -30.00 -30.00   37
 20  ω    103.00 128.00   1.00    7.50    --  108.00 -61.00 -90.00   25
 21  ω     46.00  79.00   1.00    7.50    --  108.00 -30.00 -30.00   33
 22  ω     38.00 122.00   1.00    7.50    --  108.00 -45.00 120.00   84
 23  ω     46.00  84.00   1.00    7.50    --  108.00 -61.00 -90.00   38
 24  ω     96.00 159.00   1.00    7.50    --  108.00  30.00-120.00   63
 25  ω     49.00 108.00   1.00    7.50    --  108.00 -94.00 150.00   59
 26  ω     79.00 109.00   1.00    7.50    --  108.00-111.00 150.00   30
 27  ω     55.00  97.00   1.00    7.50    --  108.00 -94.00-120.00   42
 28  ω     83.00 109.00   1.00    7.50    --  108.00 -94.00  30.00   26
 29  ω    102.00 134.00   1.00    7.50    --  108.00 -30.00  60.00   32
 30  ω     39.00  72.00   1.00    7.50    --  108.00 -30.00  60.00   33
 31  ω     49.00 100.00   1.00    7.50    --  108.00 -94.00   0.00   51
 32  ω     89.00 178.00   1.00    7.50    --  108.00  30.00 -60.00   89
 33  ω     41.00 121.00   1.00    7.50    --  108.00 -30.00 -90.00   80
 34  ω     40.00 123.00   1.00    7.50    --  108.00 -61.00  30.00   83
;
_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      -0.1313092000
_diffrn_orient_matrix_UB_12      0.0060174000
_diffrn_orient_matrix_UB_13      0.0026340000
_diffrn_orient_matrix_UB_21      -0.0057289000
_diffrn_orient_matrix_UB_22      0.1529625000
_diffrn_orient_matrix_UB_23      -0.0231322000
_diffrn_orient_matrix_UB_31      -0.0416550000
_diffrn_orient_matrix_UB_32      -0.0401450000
_diffrn_orient_matrix_UB_33      -0.0876673000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2877
_reflns_number_total             3427
_reflns_odcompleteness_completeness 99.97
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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         0.211
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0047(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3427
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.033
_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)+(0.0625P)²+0.2970P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1133
_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:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13), C18(H18), C19(H19), C20(H20), C21(H21)
2.d X=CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.e Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_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
S1 S 0.26549(4) 0.88027(4) 0.32189(3) 0.04333(17) Uani 1 1 d . . . . .
O1 O 0.27123(14) 0.86467(16) 0.24269(8) 0.0575(4) Uani 1 1 d . . . . .
O2 O 0.26165(13) 1.01481(14) 0.35399(9) 0.0561(4) Uani 1 1 d . . . . .
O3 O 0.14014(11) 0.74732(13) 0.45395(7) 0.0456(3) Uani 1 1 d . . . . .
O4 O -0.19856(16) 0.8977(2) 0.41811(12) 0.0829(6) Uani 1 1 d . . . . .
N1 N 0.14022(13) 0.80347(15) 0.32565(9) 0.0418(4) Uani 1 1 d . . . . .
N2 N -0.14008(19) 0.9867(2) 0.24571(12) 0.0695(5) Uani 1 1 d . . . . .
C1 C 0.11817(17) 0.66218(19) 0.29288(12) 0.0474(4) Uani 1 1 d . . . . .
H1A H 0.1588 0.5960 0.3322 0.057 Uiso 1 1 calc R . . . .
H1B H 0.1497 0.6535 0.2476 0.057 Uiso 1 1 calc R . . . .
C2 C -0.01345(18) 0.63344(19) 0.26887(12) 0.0478(4) Uani 1 1 d . . . . .
C3 C -0.07675(18) 0.6662(2) 0.33021(12) 0.0493(4) Uani 1 1 d . . . . .
H3A H -0.0515 0.6026 0.3739 0.059 Uiso 1 1 calc R . . . .
H3B H -0.1624 0.6562 0.3079 0.059 Uiso 1 1 calc R . . . .
C4 C -0.04763(16) 0.81601(19) 0.36039(11) 0.0430(4) Uani 1 1 d . . . . .
C5 C 0.08943(15) 0.83653(18) 0.38828(11) 0.0403(4) Uani 1 1 d . . . . .
H5 H 0.1075 0.9323 0.4042 0.048 Uiso 1 1 calc R . . . .
C6 C -0.0684(2) 0.5822(3) 0.19918(14) 0.0650(6) Uani 1 1 d . . . . .
H6A H -0.0252 0.5628 0.1632 0.078 Uiso 1 1 calc R . . . .
H6B H -0.1503 0.5654 0.1860 0.078 Uiso 1 1 calc R . . . .
C7 C -0.09844(18) 0.9130(2) 0.29577(13) 0.0498(5) Uani 1 1 d . . . . .
C8 C 0.38680(16) 0.78994(19) 0.38301(11) 0.0436(4) Uani 1 1 d . . . . .
C9 C 0.4367(2) 0.6822(2) 0.35200(12) 0.0572(5) Uani 1 1 d . . . . .
H9 H 0.4060 0.6570 0.2995 0.069 Uiso 1 1 calc R . . . .
C10 C 0.5328(2) 0.6123(3) 0.40003(14) 0.0640(6) Uani 1 1 d . . . . .
H10 H 0.5665 0.5401 0.3791 0.077 Uiso 1 1 calc R . . . .
C11 C 0.58009(18) 0.6467(2) 0.47805(14) 0.0560(5) Uani 1 1 d . . . . .
C12 C 0.5284(2) 0.7540(3) 0.50791(14) 0.0643(6) Uani 1 1 d . . . . .
H12 H 0.5590 0.7785 0.5605 0.077 Uiso 1 1 calc R . . . .
C13 C 0.43169(19) 0.8261(2) 0.46123(13) 0.0575(5) Uani 1 1 d . . . . .
H13 H 0.3976 0.8978 0.4823 0.069 Uiso 1 1 calc R . . . .
C14 C 0.6841(2) 0.5672(3) 0.52917(17) 0.0742(7) Uani 1 1 d . . . . .
H14A H 0.6625 0.4722 0.5299 0.111 Uiso 1 1 calc GR . . . .
H14B H 0.7040 0.6031 0.5818 0.111 Uiso 1 1 calc GR . . . .
H14C H 0.7519 0.5758 0.5084 0.111 Uiso 1 1 calc GR . . . .
C15 C -0.10165(18) 0.8447(2) 0.42892(13) 0.0503(5) Uani 1 1 d . . . . .
C16 C -0.02813(17) 0.79769(18) 0.50552(12) 0.0450(4) Uani 1 1 d . . . . .
C17 C 0.08824(17) 0.75069(18) 0.51486(11) 0.0435(4) Uani 1 1 d . . . . .
C18 C 0.1560(2) 0.7007(2) 0.58704(12) 0.0560(5) Uani 1 1 d . . . . .
H18 H 0.2341 0.6707 0.5934 0.067 Uiso 1 1 calc R . . . .
C19 C 0.1053(3) 0.6963(3) 0.64915(13) 0.0672(6) Uani 1 1 d . . . . .
H19 H 0.1498 0.6619 0.6975 0.081 Uiso 1 1 calc R . . . .
C20 C -0.0106(3) 0.7420(3) 0.64097(14) 0.0673(6) Uani 1 1 d . . . . .
H20 H -0.0435 0.7379 0.6834 0.081 Uiso 1 1 calc R . . . .
C21 C -0.0760(2) 0.7931(2) 0.57029(13) 0.0547(5) Uani 1 1 d . . . . .
H21 H -0.1532 0.8253 0.5650 0.066 Uiso 1 1 calc R . . . .


_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 1.4267(15) . ?
S1 O2 1.4330(15) . ?
S1 N1 1.6538(15) . ?
S1 C8 1.758(2) . ?
O3 C5 1.439(2) . ?
O3 C17 1.370(2) . ?
O4 C15 1.205(3) . ?
N1 C1 1.487(2) . ?
N1 C5 1.426(2) . ?
N2 C7 1.139(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.497(3) . ?
C2 C3 1.501(3) . ?
C2 C6 1.319(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.558(3) . ?
C4 C5 1.545(2) . ?
C4 C7 1.474(3) . ?
C4 C15 1.534(3) . ?
C5 H5 0.9800 . ?
C6 H6A 0.9300 . ?
C6 H6B 0.9300 . ?
C8 C9 1.383(3) . ?
C8 C13 1.382(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.381(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.377(3) . ?
C11 C12 1.380(3) . ?
C11 C14 1.509(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.388(3) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.461(3) . ?
C16 C17 1.394(3) . ?
C16 C21 1.403(3) . ?
C17 C18 1.390(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.381(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.388(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.365(3) . ?
C21 H21 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 120.01(9) . . ?
O1 S1 N1 105.65(9) . . ?
O1 S1 C8 107.67(9) . . ?
O2 S1 N1 105.91(8) . . ?
O2 S1 C8 108.73(9) . . ?
N1 S1 C8 108.38(8) . . ?
C17 O3 C5 116.55(14) . . ?
C1 N1 S1 117.52(12) . . ?
C5 N1 S1 119.03(12) . . ?
C5 N1 C1 116.54(14) . . ?
N1 C1 H1A 109.7 . . ?
N1 C1 H1B 109.7 . . ?
N1 C1 C2 109.67(15) . . ?
H1A C1 H1B 108.2 . . ?
C2 C1 H1A 109.7 . . ?
C2 C1 H1B 109.7 . . ?
C1 C2 C3 114.87(17) . . ?
C6 C2 C1 122.0(2) . . ?
C6 C2 C3 123.1(2) . . ?
C2 C3 H3A 109.7 . . ?
C2 C3 H3B 109.7 . . ?
C2 C3 C4 110.04(16) . . ?
H3A C3 H3B 108.2 . . ?
C4 C3 H3A 109.7 . . ?
C4 C3 H3B 109.7 . . ?
C5 C4 C3 109.77(15) . . ?
C7 C4 C3 109.36(16) . . ?
C7 C4 C5 108.83(15) . . ?
C7 C4 C15 109.30(16) . . ?
C15 C4 C3 110.06(15) . . ?
C15 C4 C5 109.50(15) . . ?
O3 C5 C4 109.70(14) . . ?
O3 C5 H5 109.6 . . ?
N1 C5 O3 108.89(14) . . ?
N1 C5 C4 109.46(15) . . ?
N1 C5 H5 109.6 . . ?
C4 C5 H5 109.6 . . ?
C2 C6 H6A 120.0 . . ?
C2 C6 H6B 120.0 . . ?
H6A C6 H6B 120.0 . . ?
N2 C7 C4 178.5(2) . . ?
C9 C8 S1 119.28(16) . . ?
C13 C8 S1 120.36(15) . . ?
C13 C8 C9 120.35(19) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 C8 119.1(2) . . ?
C10 C9 H9 120.5 . . ?
C9 C10 H10 119.1 . . ?
C11 C10 C9 121.9(2) . . ?
C11 C10 H10 119.1 . . ?
C10 C11 C12 118.1(2) . . ?
C10 C11 C14 120.5(2) . . ?
C12 C11 C14 121.4(2) . . ?
C11 C12 H12 119.3 . . ?
C11 C12 C13 121.5(2) . . ?
C13 C12 H12 119.3 . . ?
C8 C13 C12 119.1(2) . . ?
C8 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C15 C4 121.3(2) . . ?
O4 C15 C16 124.3(2) . . ?
C16 C15 C4 114.30(16) . . ?
C17 C16 C15 120.93(17) . . ?
C17 C16 C21 118.80(19) . . ?
C21 C16 C15 120.20(19) . . ?
O3 C17 C16 122.45(17) . . ?
O3 C17 C18 116.80(18) . . ?
C18 C17 C16 120.72(18) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 C17 118.8(2) . . ?
C19 C18 H18 120.6 . . ?
C18 C19 H19 119.3 . . ?
C18 C19 C20 121.4(2) . . ?
C20 C19 H19 119.3 . . ?
C19 C20 H20 120.2 . . ?
C21 C20 C19 119.5(2) . . ?
C21 C20 H20 120.2 . . ?
C16 C21 H21 119.6 . . ?
C20 C21 C16 120.8(2) . . ?
C20 C21 H21 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C1 C2 -155.44(14) . . . . ?
S1 N1 C5 O3 -88.48(15) . . . . ?
S1 N1 C5 C4 151.61(12) . . . . ?
S1 C8 C9 C10 179.36(18) . . . . ?
S1 C8 C13 C12 -179.28(17) . . . . ?
O1 S1 N1 C1 49.44(16) . . . . ?
O1 S1 N1 C5 -160.63(14) . . . . ?
O1 S1 C8 C9 -24.68(19) . . . . ?
O1 S1 C8 C13 155.42(17) . . . . ?
O2 S1 N1 C1 177.75(14) . . . . ?
O2 S1 N1 C5 -32.31(16) . . . . ?
O2 S1 C8 C9 -156.15(16) . . . . ?
O2 S1 C8 C13 23.95(19) . . . . ?
O3 C17 C18 C19 -177.09(19) . . . . ?
O4 C15 C16 C17 -173.1(2) . . . . ?
O4 C15 C16 C21 9.9(3) . . . . ?
N1 S1 C8 C9 89.16(17) . . . . ?
N1 S1 C8 C13 -90.74(18) . . . . ?
N1 C1 C2 C3 -49.7(2) . . . . ?
N1 C1 C2 C6 130.8(2) . . . . ?
C1 N1 C5 O3 61.75(19) . . . . ?
C1 N1 C5 C4 -58.2(2) . . . . ?
C1 C2 C3 C4 52.0(2) . . . . ?
C2 C3 C4 C5 -53.6(2) . . . . ?
C2 C3 C4 C7 65.7(2) . . . . ?
C2 C3 C4 C15 -174.21(16) . . . . ?
C3 C4 C5 O3 -63.10(19) . . . . ?
C3 C4 C5 N1 56.32(19) . . . . ?
C3 C4 C15 O4 -94.5(2) . . . . ?
C3 C4 C15 C16 83.2(2) . . . . ?
C4 C15 C16 C17 9.2(3) . . . . ?
C4 C15 C16 C21 -167.75(17) . . . . ?
C5 O3 C17 C16 21.4(2) . . . . ?
C5 O3 C17 C18 -160.51(16) . . . . ?
C5 N1 C1 C2 53.9(2) . . . . ?
C5 C4 C15 O4 144.8(2) . . . . ?
C5 C4 C15 C16 -37.5(2) . . . . ?
C6 C2 C3 C4 -128.5(2) . . . . ?
C7 C4 C5 O3 177.25(15) . . . . ?
C7 C4 C5 N1 -63.33(19) . . . . ?
C7 C4 C15 O4 25.6(3) . . . . ?
C7 C4 C15 C16 -156.65(17) . . . . ?
C8 S1 N1 C1 -65.72(16) . . . . ?
C8 S1 N1 C5 84.21(15) . . . . ?
C8 C9 C10 C11 0.2(4) . . . . ?
C9 C8 C13 C12 0.8(3) . . . . ?
C9 C10 C11 C12 0.2(4) . . . . ?
C9 C10 C11 C14 179.2(2) . . . . ?
C10 C11 C12 C13 -0.1(4) . . . . ?
C11 C12 C13 C8 -0.4(4) . . . . ?
C13 C8 C9 C10 -0.7(3) . . . . ?
C14 C11 C12 C13 -179.1(2) . . . . ?
C15 C4 C5 O3 57.83(18) . . . . ?
C15 C4 C5 N1 177.25(14) . . . . ?
C15 C16 C17 O3 0.7(3) . . . . ?
C15 C16 C17 C18 -177.27(18) . . . . ?
C15 C16 C21 C20 176.2(2) . . . . ?
C16 C17 C18 C19 1.0(3) . . . . ?
C17 O3 C5 N1 -170.39(14) . . . . ?
C17 O3 C5 C4 -50.6(2) . . . . ?
C17 C16 C21 C20 -0.8(3) . . . . ?
C17 C18 C19 C20 -0.7(4) . . . . ?
C18 C19 C20 C21 -0.3(4) . . . . ?
C19 C20 C21 C16 1.1(3) . . . . ?
C21 C16 C17 O3 177.75(16) . . . . ?
C21 C16 C17 C18 -0.3(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 1.211
_oxdiff_exptl_absorpt_empirical_full_min 0.885
