# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 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_201117_s4_sws_1
_database_code_depnum_ccdc_archive 'CCDC 2222506'
loop_
_audit_author_name
_audit_author_address
Four-azaindoline-one
;Chengdu Institute of Biology
China
;
_audit_update_record             
;
2022-11-27 deposited with the CCDC.	2024-01-10 downloaded from the CCDC.
;
_audit_creation_date             2020-11-17
_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         'C17 H16 Cl N3 O3 S'
_chemical_formula_sum            'C17 H16 Cl N3 O3 S'
_chemical_formula_weight         377.84
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3cl1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.4261(5)
_cell_length_b                   9.6846(4)
_cell_length_c                   16.4306(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.775(4)
_cell_angle_gamma                90
_cell_volume                     1765.86(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2263
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.1390
_cell_measurement_theta_min      3.4560
_shelx_estimated_absorpt_T_max   0.916
_shelx_estimated_absorpt_T_min   0.886
_exptl_absorpt_coefficient_mu    0.356
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89385
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8593
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         3.247
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -30.00   42.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773   57.0000   30.0000 72

#__ type_ start__ end____ width___ exp.time_
  2 omega  -25.00    1.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773   57.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -21.00   15.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773  -99.0000  150.0000 36

#__ type_ start__ end____ width___ exp.time_
  4 omega  -82.00  -56.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773 -178.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega  -84.00    3.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.4773  -38.0000 -150.0000 87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0630673000
_diffrn_orient_matrix_UB_12      0.0093021000
_diffrn_orient_matrix_UB_13      0.0146557000
_diffrn_orient_matrix_UB_21      0.0084185000
_diffrn_orient_matrix_UB_22      -0.0725541000
_diffrn_orient_matrix_UB_23      -0.0000215000
_diffrn_orient_matrix_UB_31      0.0059548000
_diffrn_orient_matrix_UB_32      0.0032924000
_diffrn_orient_matrix_UB_33      -0.0419722000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2841
_reflns_number_total             3599
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3599
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0444
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0467P)²+0.6078P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_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:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C12(H12), C13(H13), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Cl1 Cl 0.67271(5) 0.41996(6) 0.36286(4) 0.04566(19) Uani 1 1 d . . . . .
S1 S 0.78647(5) 0.89598(6) 0.69789(3) 0.04060(18) Uani 1 1 d . . . . .
O1 O 0.51156(14) 0.60394(18) 0.41811(10) 0.0459(4) Uani 1 1 d . . . . .
O2 O 0.67951(15) 0.95999(18) 0.65080(10) 0.0506(4) Uani 1 1 d . . . . .
O3 O 0.88284(16) 0.97606(18) 0.74681(10) 0.0529(5) Uani 1 1 d . . . . .
N1 N 0.83024(16) 0.54773(19) 0.47844(11) 0.0358(4) Uani 1 1 d . . . . .
N2 N 0.84695(16) 0.8153(2) 0.62921(10) 0.0389(5) Uani 1 1 d . . . . .
N3 N 1.0912(2) 0.8099(3) 0.48269(16) 0.0721(8) Uani 1 1 d . . . . .
C1 C 0.7143(2) 0.5401(2) 0.44253(13) 0.0357(5) Uani 1 1 d . . . . .
C2 C 0.6251(2) 0.6237(2) 0.46371(13) 0.0363(5) Uani 1 1 d . . . . .
C3 C 0.6605(2) 0.7187(2) 0.52828(13) 0.0374(5) Uani 1 1 d . . . . .
H3 H 0.6048 0.7752 0.5451 0.045 Uiso 1 1 calc R . . . .
C4 C 0.7823(2) 0.7258(2) 0.56649(12) 0.0342(5) Uani 1 1 d . . . . .
C5 C 0.9723(2) 0.7623(3) 0.65784(14) 0.0503(7) Uani 1 1 d . . . . .
H5A H 0.9813 0.7076 0.7084 0.060 Uiso 1 1 calc R . . . .
H5B H 1.0297 0.8378 0.6688 0.060 Uiso 1 1 calc R . . . .
C6 C 0.9908(2) 0.6731(3) 0.58490(14) 0.0417(6) Uani 1 1 d . . . . .
H6 H 1.0357 0.5889 0.6055 0.050 Uiso 1 1 calc R . . . .
C7 C 0.86214(19) 0.6393(2) 0.53979(13) 0.0349(5) Uani 1 1 d . . . . .
C8 C 0.4197(2) 0.6995(3) 0.42848(15) 0.0476(6) Uani 1 1 d . . . . .
H8A H 0.4448 0.7937 0.4218 0.057 Uiso 1 1 calc R . . . .
H8B H 0.4047 0.6901 0.4839 0.057 Uiso 1 1 calc R . . . .
C9 C 0.3081(2) 0.6659(4) 0.36268(19) 0.0691(9) Uani 1 1 d . . . . .
H9A H 0.3229 0.6805 0.3082 0.104 Uiso 1 1 calc GR . . . .
H9B H 0.2434 0.7245 0.3696 0.104 Uiso 1 1 calc GR . . . .
H9C H 0.2867 0.5711 0.3681 0.104 Uiso 1 1 calc GR . . . .
C10 C 1.0496(2) 0.7495(3) 0.52832(15) 0.0473(6) Uani 1 1 d . . . . .
C11 C 0.7452(2) 0.7668(2) 0.76109(13) 0.0387(5) Uani 1 1 d . . . . .
C12 C 0.6281(2) 0.7206(3) 0.74553(14) 0.0494(6) Uani 1 1 d . . . . .
H12 H 0.5702 0.7572 0.7011 0.059 Uiso 1 1 calc R . . . .
C13 C 0.5965(2) 0.6198(3) 0.79590(15) 0.0509(7) Uani 1 1 d . . . . .
H13 H 0.5172 0.5890 0.7850 0.061 Uiso 1 1 calc R . . . .
C14 C 0.6807(2) 0.5641(2) 0.86209(14) 0.0413(6) Uani 1 1 d . . . . .
C15 C 0.7988(2) 0.6100(3) 0.87611(15) 0.0453(6) Uani 1 1 d . . . . .
H15 H 0.8571 0.5716 0.9195 0.054 Uiso 1 1 calc R . . . .
C16 C 0.8318(2) 0.7117(3) 0.82692(14) 0.0444(6) Uani 1 1 d . . . . .
H16 H 0.9110 0.7428 0.8378 0.053 Uiso 1 1 calc R . . . .
C17 C 0.6444(2) 0.4576(3) 0.91821(17) 0.0565(7) Uani 1 1 d . . . . .
H17A H 0.6607 0.3670 0.9000 0.085 Uiso 1 1 calc GR . . . .
H17B H 0.5598 0.4662 0.9155 0.085 Uiso 1 1 calc GR . . . .
H17C H 0.6894 0.4718 0.9749 0.085 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
Cl1 C1 1.731(2) . ?
S1 O2 1.4234(17) . ?
S1 O3 1.4278(17) . ?
S1 N2 1.6532(18) . ?
S1 C11 1.760(2) . ?
O1 C2 1.348(3) . ?
O1 C8 1.440(3) . ?
N1 C1 1.318(3) . ?
N1 C7 1.327(3) . ?
N2 C4 1.412(3) . ?
N2 C5 1.488(3) . ?
N3 C10 1.141(3) . ?
C1 C2 1.409(3) . ?
C2 C3 1.390(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(3) . ?
C4 C7 1.384(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.532(3) . ?
C6 H6 0.9800 . ?
C6 C7 1.516(3) . ?
C6 C10 1.470(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.498(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C11 C12 1.376(3) . ?
C11 C16 1.387(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.382(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.379(3) . ?
C14 C15 1.387(3) . ?
C14 C17 1.506(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.382(3) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O3 121.11(11) . . ?
O2 S1 N2 106.22(9) . . ?
O2 S1 C11 108.29(11) . . ?
O3 S1 N2 104.44(10) . . ?
O3 S1 C11 109.45(10) . . ?
N2 S1 C11 106.33(10) . . ?
C2 O1 C8 118.36(18) . . ?
C1 N1 C7 116.28(19) . . ?
C4 N2 S1 123.86(15) . . ?
C4 N2 C5 108.41(18) . . ?
C5 N2 S1 118.33(14) . . ?
N1 C1 Cl1 116.24(17) . . ?
N1 C1 C2 124.5(2) . . ?
C2 C1 Cl1 119.24(17) . . ?
O1 C2 C1 115.98(19) . . ?
O1 C2 C3 125.8(2) . . ?
C3 C2 C1 118.2(2) . . ?
C2 C3 H3 121.4 . . ?
C4 C3 C2 117.2(2) . . ?
C4 C3 H3 121.4 . . ?
C3 C4 N2 130.9(2) . . ?
C7 C4 N2 109.46(19) . . ?
C7 C4 C3 119.5(2) . . ?
N2 C5 H5A 110.9 . . ?
N2 C5 H5B 110.9 . . ?
N2 C5 C6 104.39(17) . . ?
H5A C5 H5B 108.9 . . ?
C6 C5 H5A 110.9 . . ?
C6 C5 H5B 110.9 . . ?
C5 C6 H6 110.9 . . ?
C7 C6 C5 101.90(18) . . ?
C7 C6 H6 110.9 . . ?
C10 C6 C5 112.3(2) . . ?
C10 C6 H6 110.9 . . ?
C10 C6 C7 109.61(18) . . ?
N1 C7 C4 124.3(2) . . ?
N1 C7 C6 125.08(19) . . ?
C4 C7 C6 110.45(19) . . ?
O1 C8 H8A 110.3 . . ?
O1 C8 H8B 110.3 . . ?
O1 C8 C9 107.1(2) . . ?
H8A C8 H8B 108.6 . . ?
C9 C8 H8A 110.3 . . ?
C9 C8 H8B 110.3 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C10 C6 177.5(3) . . ?
C12 C11 S1 120.47(18) . . ?
C12 C11 C16 120.1(2) . . ?
C16 C11 S1 119.45(18) . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.0(2) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.1(2) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 C15 118.3(2) . . ?
C13 C14 C17 120.6(2) . . ?
C15 C14 C17 121.1(2) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 C14 121.4(2) . . ?
C16 C15 H15 119.3 . . ?
C11 C16 H16 120.4 . . ?
C15 C16 C11 119.2(2) . . ?
C15 C16 H16 120.4 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
Cl1 C1 C2 O1 -0.9(3) . . . . ?
Cl1 C1 C2 C3 179.56(17) . . . . ?
S1 N2 C4 C3 24.6(3) . . . . ?
S1 N2 C4 C7 -158.96(16) . . . . ?
S1 N2 C5 C6 170.26(16) . . . . ?
S1 C11 C12 C13 -179.58(19) . . . . ?
S1 C11 C16 C15 -179.78(18) . . . . ?
O1 C2 C3 C4 -178.5(2) . . . . ?
O2 S1 N2 C4 -49.6(2) . . . . ?
O2 S1 N2 C5 167.91(18) . . . . ?
O2 S1 C11 C12 15.2(2) . . . . ?
O2 S1 C11 C16 -164.78(18) . . . . ?
O3 S1 N2 C4 -178.67(18) . . . . ?
O3 S1 N2 C5 38.8(2) . . . . ?
O3 S1 C11 C12 149.18(19) . . . . ?
O3 S1 C11 C16 -30.8(2) . . . . ?
N1 C1 C2 O1 177.9(2) . . . . ?
N1 C1 C2 C3 -1.7(3) . . . . ?
N2 S1 C11 C12 -98.5(2) . . . . ?
N2 S1 C11 C16 81.4(2) . . . . ?
N2 C4 C7 N1 -176.6(2) . . . . ?
N2 C4 C7 C6 -1.7(3) . . . . ?
N2 C5 C6 C7 -21.9(3) . . . . ?
N2 C5 C6 C10 95.3(2) . . . . ?
C1 N1 C7 C4 -0.8(3) . . . . ?
C1 N1 C7 C6 -175.0(2) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
C2 O1 C8 C9 172.1(2) . . . . ?
C2 C3 C4 N2 175.7(2) . . . . ?
C2 C3 C4 C7 -0.4(3) . . . . ?
C3 C4 C7 N1 0.3(3) . . . . ?
C3 C4 C7 C6 175.2(2) . . . . ?
C4 N2 C5 C6 22.4(3) . . . . ?
C5 N2 C4 C3 170.2(2) . . . . ?
C5 N2 C4 C7 -13.3(2) . . . . ?
C5 C6 C7 N1 -170.0(2) . . . . ?
C5 C6 C7 C4 15.2(3) . . . . ?
C7 N1 C1 Cl1 -179.69(16) . . . . ?
C7 N1 C1 C2 1.5(3) . . . . ?
C8 O1 C2 C1 -171.1(2) . . . . ?
C8 O1 C2 C3 8.5(3) . . . . ?
C10 C6 C7 N1 70.9(3) . . . . ?
C10 C6 C7 C4 -104.0(2) . . . . ?
C11 S1 N2 C4 65.6(2) . . . . ?
C11 S1 N2 C5 -76.9(2) . . . . ?
C11 C12 C13 C14 0.0(4) . . . . ?
C12 C11 C16 C15 0.2(4) . . . . ?
C12 C13 C14 C15 -1.1(4) . . . . ?
C12 C13 C14 C17 178.0(2) . . . . ?
C13 C14 C15 C16 1.8(4) . . . . ?
C14 C15 C16 C11 -1.3(4) . . . . ?
C16 C11 C12 C13 0.4(4) . . . . ?
C17 C14 C15 C16 -177.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_221011_s4_lyz
_database_code_depnum_ccdc_archive 'CCDC 2222507'
loop_
_audit_author_name
_audit_author_address
'Yazhou Liu'
;Chengdu Institute of Biology
China
;
_audit_update_record             
;
2022-11-27 deposited with the CCDC.	2024-01-10 downloaded from the CCDC.
;
_audit_creation_date             2022-10-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H19 Br N2 O4 S2, C3 H6 O'
_chemical_formula_sum            'C24 H25 Br N2 O5 S2'
_chemical_formula_weight         565.49
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.1423(8)
_cell_length_b                   12.2839(8)
_cell_length_c                   12.9853(9)
_cell_angle_alpha                92.802(6)
_cell_angle_beta                 98.268(7)
_cell_angle_gamma                103.730(7)
_cell_volume                     1243.89(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1959
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.2890
_cell_measurement_theta_min      3.3200
_shelx_estimated_absorpt_T_max   0.654
_shelx_estimated_absorpt_T_min   0.562
_exptl_absorpt_coefficient_mu    1.858
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79581
_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            ?
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0724
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10277
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         3.182
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -2.00  49.00   1.00    2.25    --  -15.48  57.00 -60.00   51
  2  ω    -42.00  52.00   1.00    2.25    --  -15.48  77.00 150.00   94
  3  ω    -17.00  19.00   1.00    2.25    --  -15.48 -99.00 -60.00   36
  4  ω    -19.00  39.00   1.00    2.25    --  -15.48  57.00-150.00   58
  5  ω      3.00  79.00   1.00    2.25    --   17.66  57.00 -60.00   76
  6  ω     -8.00  85.00   1.00    2.25    --   17.66  77.00  60.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0208346000
_diffrn_orient_matrix_UB_12      -0.0573454000
_diffrn_orient_matrix_UB_13      0.0105406000
_diffrn_orient_matrix_UB_21      0.0129889000
_diffrn_orient_matrix_UB_22      0.0164513000
_diffrn_orient_matrix_UB_23      0.0542679000
_diffrn_orient_matrix_UB_31      -0.0874683000
_diffrn_orient_matrix_UB_32      0.0007814000
_diffrn_orient_matrix_UB_33      -0.0036688000
_diffrn_oxdiff_digest_frames     
;
0127f5b8d7120ecf6fefb0bdba1d1d016000029311c
;
_diffrn_oxdiff_digest_hkl        
;
01e62c10eb1c671a073b62e8949411a15be98b
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3207
_reflns_number_total             5093
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         5093
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1004
_refine_ls_R_factor_gt           0.0543
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0578P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1347
_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:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13), C16(H16), C17(H17),
 C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C24(H24A,H24B,
 H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.61686(6) 0.67646(4) 0.12954(3) 0.0655(2) Uani 1 1 d . . . . .
S1 S 0.68219(13) 0.29613(9) 0.48346(8) 0.0505(3) Uani 1 1 d . . . . .
O1 O 0.5278(3) 0.3126(2) 0.4258(2) 0.0659(9) Uani 1 1 d . . . . .
N1 N 0.8122(4) 0.5431(3) 0.3883(2) 0.0497(9) Uani 1 1 d . . . . .
C1 C 0.7024(5) 0.5766(3) 0.2172(3) 0.0431(9) Uani 1 1 d . . . . .
S2 S 0.74880(13) 0.21301(8) 0.12205(8) 0.0450(3) Uani 1 1 d . . . . .
O2 O 0.6896(4) 0.1840(2) 0.5052(2) 0.0670(9) Uani 1 1 d . . . . .
N2 N 0.7974(4) 0.2976(3) 0.2284(2) 0.0470(8) Uani 1 1 d . . . . .
C2 C 0.7569(5) 0.6104(3) 0.3212(3) 0.0497(10) Uani 1 1 d . . . . .
H2 H 0.755178 0.682520 0.345696 0.060 Uiso 1 1 calc R . . . .
O3 O 0.8749(3) 0.1495(2) 0.1289(2) 0.0580(8) Uani 1 1 d . . . . .
C3 C 0.8142(5) 0.4426(3) 0.3493(3) 0.0416(9) Uani 1 1 d . . . . .
O4 O 0.7283(4) 0.2807(2) 0.03784(19) 0.0563(8) Uani 1 1 d . . . . .
C4 C 0.8558(5) 0.3506(3) 0.4117(3) 0.0439(10) Uani 1 1 d . . . . .
H4 H 0.965274 0.377017 0.458857 0.053 Uiso 1 1 calc R . . . .
C5 C 0.8653(5) 0.2608(3) 0.3280(3) 0.0507(11) Uani 1 1 d . . . . .
H5A H 0.982657 0.256029 0.328788 0.061 Uiso 1 1 calc R . . . .
H5B H 0.796670 0.187678 0.339681 0.061 Uiso 1 1 calc R . . . .
C6 C 0.7685(4) 0.4052(3) 0.2435(3) 0.0381(9) Uani 1 1 d . . . . .
C7 C 0.7074(5) 0.4727(3) 0.1745(3) 0.0422(9) Uani 1 1 d . . . . .
H7 H 0.671930 0.450028 0.103745 0.051 Uiso 1 1 calc R . . . .
C8 C 0.7290(5) 0.3782(3) 0.6021(3) 0.0469(10) Uani 1 1 d . . . . .
C9 C 0.6872(5) 0.4808(4) 0.6098(3) 0.0539(11) Uani 1 1 d . . . . .
H9 H 0.638283 0.508176 0.550519 0.065 Uiso 1 1 calc R . . . .
C10 C 0.7183(5) 0.5425(4) 0.7055(3) 0.0583(12) Uani 1 1 d . . . . .
H10 H 0.689187 0.611128 0.710282 0.070 Uiso 1 1 calc R . . . .
C11 C 0.7919(5) 0.5035(4) 0.7943(3) 0.0567(11) Uani 1 1 d . . . . .
C12 C 0.8332(6) 0.4014(4) 0.7850(3) 0.0618(12) Uani 1 1 d . . . . .
H12 H 0.882112 0.374054 0.844276 0.074 Uiso 1 1 calc R . . . .
C13 C 0.8038(5) 0.3387(4) 0.6901(3) 0.0571(11) Uani 1 1 d . . . . .
H13 H 0.833960 0.270374 0.685503 0.069 Uiso 1 1 calc R . . . .
C14 C 0.8212(7) 0.5695(4) 0.8986(4) 0.0803(15) Uani 1 1 d . . . . .
H14A H 0.830619 0.647528 0.888595 0.120 Uiso 1 1 calc GR . . . .
H14B H 0.925098 0.561242 0.939252 0.120 Uiso 1 1 calc GR . . . .
H14C H 0.726727 0.541894 0.934664 0.120 Uiso 1 1 calc GR . . . .
C15 C 0.5510(5) 0.1209(3) 0.1285(3) 0.0407(9) Uani 1 1 d . . . . .
C16 C 0.5409(5) 0.0104(3) 0.1467(3) 0.0511(11) Uani 1 1 d . . . . .
H16 H 0.639831 -0.015667 0.156845 0.061 Uiso 1 1 calc R . . . .
C17 C 0.3848(5) -0.0614(4) 0.1498(3) 0.0567(11) Uani 1 1 d . . . . .
H17 H 0.378768 -0.136164 0.161636 0.068 Uiso 1 1 calc R . . . .
C18 C 0.2358(5) -0.0241(4) 0.1356(3) 0.0525(11) Uani 1 1 d . . . . .
C19 C 0.2516(6) 0.0878(4) 0.1172(4) 0.0631(13) Uani 1 1 d . . . . .
H19 H 0.153347 0.114595 0.106935 0.076 Uiso 1 1 calc R . . . .
C20 C 0.4052(5) 0.1599(4) 0.1136(3) 0.0558(11) Uani 1 1 d . . . . .
H20 H 0.411667 0.234628 0.101170 0.067 Uiso 1 1 calc R . . . .
C21 C 0.0647(5) -0.1022(4) 0.1375(4) 0.0741(14) Uani 1 1 d . . . . .
H21A H 0.057636 -0.172632 0.099471 0.111 Uiso 1 1 calc GR . . . .
H21B H -0.023999 -0.069522 0.105663 0.111 Uiso 1 1 calc GR . . . .
H21C H 0.050825 -0.114565 0.208464 0.111 Uiso 1 1 calc GR . . . .
O5 O 0.1018(5) 0.1693(3) 0.5054(3) 0.0982(13) Uani 1 1 d . . . . .
C22 C 0.2186(7) 0.0591(4) 0.3989(4) 0.0886(17) Uani 1 1 d . . . . .
H22A H 0.142457 0.078872 0.343510 0.133 Uiso 1 1 calc GR . . . .
H22B H 0.193381 -0.021299 0.399501 0.133 Uiso 1 1 calc GR . . . .
H22C H 0.334799 0.086961 0.388110 0.133 Uiso 1 1 calc GR . . . .
C23 C 0.1957(6) 0.1091(4) 0.4996(4) 0.0626(12) Uani 1 1 d . . . . .
C24 C 0.2932(7) 0.0788(4) 0.5950(4) 0.0864(17) Uani 1 1 d . . . . .
H24A H 0.273529 0.119107 0.655384 0.130 Uiso 1 1 calc GR . . . .
H24B H 0.413202 0.098220 0.590671 0.130 Uiso 1 1 calc GR . . . .
H24C H 0.255789 -0.000624 0.600587 0.130 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 C1 1.897(4) . ?
S1 O1 1.431(3) . ?
S1 O2 1.433(3) . ?
S1 C4 1.818(4) . ?
S1 C8 1.741(4) . ?
N1 C2 1.335(4) . ?
N1 C3 1.316(4) . ?
C1 C2 1.370(5) . ?
C1 C7 1.379(5) . ?
S2 N2 1.628(3) . ?
S2 O3 1.425(3) . ?
S2 O4 1.421(3) . ?
S2 C15 1.751(4) . ?
N2 C5 1.468(4) . ?
N2 C6 1.406(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.497(5) . ?
C3 C6 1.395(5) . ?
C4 H4 0.9800 . ?
C4 C5 1.533(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.371(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.383(5) . ?
C8 C13 1.381(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.383(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.381(6) . ?
C11 C12 1.378(6) . ?
C11 C14 1.503(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.380(6) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.374(5) . ?
C15 C20 1.375(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.371(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.387(5) . ?
C18 C19 1.385(6) . ?
C18 C21 1.496(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.359(6) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
O5 C23 1.189(5) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C22 C23 1.473(6) . ?
C23 C24 1.485(6) . ?
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 O2 118.42(18) . . ?
O1 S1 C4 107.81(18) . . ?
O1 S1 C8 108.86(18) . . ?
O2 S1 C4 107.16(18) . . ?
O2 S1 C8 107.71(19) . . ?
C8 S1 C4 106.26(18) . . ?
C3 N1 C2 116.5(3) . . ?
C2 C1 Br1 118.6(3) . . ?
C2 C1 C7 122.3(3) . . ?
C7 C1 Br1 119.1(3) . . ?
N2 S2 C15 106.43(17) . . ?
O3 S2 N2 105.53(16) . . ?
O3 S2 C15 107.96(18) . . ?
O4 S2 N2 106.43(16) . . ?
O4 S2 O3 120.70(18) . . ?
O4 S2 C15 108.92(17) . . ?
C5 N2 S2 120.8(2) . . ?
C6 N2 S2 128.4(2) . . ?
C6 N2 C5 110.5(3) . . ?
N1 C2 C1 122.0(3) . . ?
N1 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
N1 C3 C4 125.3(3) . . ?
N1 C3 C6 124.2(3) . . ?
C6 C3 C4 110.5(3) . . ?
S1 C4 H4 111.3 . . ?
C3 C4 S1 109.4(3) . . ?
C3 C4 H4 111.3 . . ?
C3 C4 C5 103.3(3) . . ?
C5 C4 S1 110.1(3) . . ?
C5 C4 H4 111.3 . . ?
N2 C5 C4 105.3(3) . . ?
N2 C5 H5A 110.7 . . ?
N2 C5 H5B 110.7 . . ?
C4 C5 H5A 110.7 . . ?
C4 C5 H5B 110.7 . . ?
H5A C5 H5B 108.8 . . ?
C3 C6 N2 109.1(3) . . ?
C7 C6 N2 131.3(3) . . ?
C7 C6 C3 119.6(3) . . ?
C1 C7 H7 122.3 . . ?
C6 C7 C1 115.3(3) . . ?
C6 C7 H7 122.3 . . ?
C9 C8 S1 120.7(3) . . ?
C13 C8 S1 119.5(3) . . ?
C13 C8 C9 119.7(4) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0(4) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.9(4) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C14 120.7(4) . . ?
C12 C11 C10 118.3(4) . . ?
C12 C11 C14 121.0(4) . . ?
C11 C12 H12 119.1 . . ?
C11 C12 C13 121.7(4) . . ?
C13 C12 H12 119.1 . . ?
C8 C13 H13 120.3 . . ?
C12 C13 C8 119.4(4) . . ?
C12 C13 H13 120.3 . . ?
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 . . ?
C16 C15 S2 120.5(3) . . ?
C16 C15 C20 120.3(4) . . ?
C20 C15 S2 119.2(3) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 119.9(4) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.5 . . ?
C16 C17 C18 121.0(4) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 C21 121.3(4) . . ?
C19 C18 C17 117.2(4) . . ?
C19 C18 C21 121.5(4) . . ?
C18 C19 H19 118.7 . . ?
C20 C19 C18 122.5(4) . . ?
C20 C19 H19 118.7 . . ?
C15 C20 H20 120.5 . . ?
C19 C20 C15 119.0(4) . . ?
C19 C20 H20 120.5 . . ?
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 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C23 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
C23 C22 H22C 109.5 . . ?
O5 C23 C22 122.3(5) . . ?
O5 C23 C24 121.1(5) . . ?
C22 C23 C24 116.6(5) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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 C1 C2 N1 177.3(3) . . . . ?
Br1 C1 C7 C6 -179.0(3) . . . . ?
S1 C4 C5 N2 106.2(3) . . . . ?
S1 C8 C9 C10 177.0(3) . . . . ?
S1 C8 C13 C12 -176.9(3) . . . . ?
O1 S1 C4 C3 28.0(3) . . . . ?
O1 S1 C4 C5 -84.9(3) . . . . ?
O1 S1 C8 C9 -32.7(4) . . . . ?
O1 S1 C8 C13 145.1(3) . . . . ?
N1 C3 C4 S1 70.8(4) . . . . ?
N1 C3 C4 C5 -171.9(4) . . . . ?
N1 C3 C6 N2 175.7(4) . . . . ?
N1 C3 C6 C7 -4.0(6) . . . . ?
S2 N2 C5 C4 -167.4(3) . . . . ?
S2 N2 C6 C3 173.8(3) . . . . ?
S2 N2 C6 C7 -6.5(6) . . . . ?
S2 C15 C16 C17 -178.9(3) . . . . ?
S2 C15 C20 C19 179.1(3) . . . . ?
O2 S1 C4 C3 156.5(3) . . . . ?
O2 S1 C4 C5 43.6(3) . . . . ?
O2 S1 C8 C9 -162.3(3) . . . . ?
O2 S1 C8 C13 15.6(4) . . . . ?
N2 S2 C15 C16 -107.8(3) . . . . ?
N2 S2 C15 C20 73.2(3) . . . . ?
N2 C6 C7 C1 -177.5(4) . . . . ?
C2 N1 C3 C4 -174.1(4) . . . . ?
C2 N1 C3 C6 2.3(6) . . . . ?
C2 C1 C7 C6 0.8(6) . . . . ?
O3 S2 N2 C5 -36.7(3) . . . . ?
O3 S2 N2 C6 150.1(3) . . . . ?
O3 S2 C15 C16 5.1(4) . . . . ?
O3 S2 C15 C20 -173.9(3) . . . . ?
C3 N1 C2 C1 0.9(6) . . . . ?
C3 C4 C5 N2 -10.6(4) . . . . ?
C3 C6 C7 C1 2.2(5) . . . . ?
O4 S2 N2 C5 -166.1(3) . . . . ?
O4 S2 N2 C6 20.7(4) . . . . ?
O4 S2 C15 C16 137.8(3) . . . . ?
O4 S2 C15 C20 -41.2(4) . . . . ?
C4 S1 C8 C9 83.1(4) . . . . ?
C4 S1 C8 C13 -99.0(4) . . . . ?
C4 C3 C6 N2 -7.4(4) . . . . ?
C4 C3 C6 C7 172.8(3) . . . . ?
C5 N2 C6 C3 0.1(4) . . . . ?
C5 N2 C6 C7 179.8(4) . . . . ?
C6 N2 C5 C4 6.9(4) . . . . ?
C6 C3 C4 S1 -106.0(3) . . . . ?
C6 C3 C4 C5 11.2(4) . . . . ?
C7 C1 C2 N1 -2.6(6) . . . . ?
C8 S1 C4 C3 -88.6(3) . . . . ?
C8 S1 C4 C5 158.5(3) . . . . ?
C8 C9 C10 C11 0.4(7) . . . . ?
C9 C8 C13 C12 1.0(6) . . . . ?
C9 C10 C11 C12 -0.2(7) . . . . ?
C9 C10 C11 C14 -178.4(4) . . . . ?
C10 C11 C12 C13 0.4(7) . . . . ?
C11 C12 C13 C8 -0.8(7) . . . . ?
C13 C8 C9 C10 -0.8(6) . . . . ?
C14 C11 C12 C13 178.6(4) . . . . ?
C15 S2 N2 C5 77.9(3) . . . . ?
C15 S2 N2 C6 -95.3(4) . . . . ?
C15 C16 C17 C18 -0.4(6) . . . . ?
C16 C15 C20 C19 0.1(6) . . . . ?
C16 C17 C18 C19 0.6(6) . . . . ?
C16 C17 C18 C21 179.2(4) . . . . ?
C17 C18 C19 C20 -0.4(7) . . . . ?
C18 C19 C20 C15 0.1(7) . . . . ?
C20 C15 C16 C17 0.1(6) . . . . ?
C21 C18 C19 C20 -179.0(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 1.225
_oxdiff_exptl_absorpt_empirical_full_min 0.802
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2222508'
loop_
_audit_author_name
_audit_author_address
'Yazhou Liu'
;Chengdu Institute of Biology
China
;
_audit_update_record             
;
2022-11-27 deposited with the CCDC.	2024-01-10 downloaded from the CCDC.
;
_audit_creation_date             2022-10-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H23 Cl N2 O5 S'
_chemical_formula_sum            'C24 H23 Cl N2 O5 S'
_chemical_formula_weight         486.95
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.5028(18)
_cell_length_b                   9.2793(6)
_cell_length_c                   24.775(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.353(10)
_cell_angle_gamma                90
_cell_volume                     4691.9(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2010
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.6660
_cell_measurement_theta_min      3.5850
_shelx_estimated_absorpt_T_max   0.931
_shelx_estimated_absorpt_T_min   0.905
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_unetI/netI     0.0672
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            10760
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         3.027
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -83.00   1.00   0.60   75.00    --  -15.48 -57.00 -30.00  140
  2  ω    -24.00  12.60   0.60   75.00    --  -15.48 -99.00-120.00   61
  3  ω    -85.00  -3.40   0.60   75.00    --  -15.48 -38.00-120.00  136
  4  ω    -83.00 -57.80   0.60   75.00    --  -15.48 -19.00  30.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0011481000
_diffrn_orient_matrix_UB_12      0.0064638000
_diffrn_orient_matrix_UB_13      0.0282054000
_diffrn_orient_matrix_UB_21      -0.0346676000
_diffrn_orient_matrix_UB_22      0.0047344000
_diffrn_orient_matrix_UB_23      -0.0105286000
_diffrn_orient_matrix_UB_31      -0.0022526000
_diffrn_orient_matrix_UB_32      -0.0759860000
_diffrn_orient_matrix_UB_33      0.0017556000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2939
_reflns_number_total             4793
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.691
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         4793
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1341
_refine_ls_R_factor_gt           0.0881
_refine_ls_restrained_S_all      1.050
_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)+(0.0884P)²+21.3276P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2256
_refine_ls_wR_factor_ref         0.2551
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C11(H11), C12(H12), C14(H14), C15(H15), C20(H20), C21(H21), C22(H22),
 C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.46111(8) 0.76282(19) 0.38599(7) 0.0732(5) Uani 1 1 d . . . . .
S1 S 0.69759(7) 0.54679(15) 0.26040(6) 0.0504(4) Uani 1 1 d . . . . .
O1 O 0.49476(18) 0.4802(4) 0.35592(16) 0.0600(10) Uani 1 1 d . . . . .
N1 N 0.54752(19) 0.8385(5) 0.33783(18) 0.0480(10) Uani 1 1 d . . . . .
C1 C 0.5173(2) 0.7262(6) 0.3509(2) 0.0481(12) Uani 1 1 d . . . . .
O2 O 0.6570(2) 0.4236(4) 0.24151(17) 0.0656(11) Uani 1 1 d . . . . .
N2 N 0.6494(2) 0.6794(4) 0.26500(17) 0.0460(10) Uani 1 1 d . . . . .
C2 C 0.5282(2) 0.5818(5) 0.3381(2) 0.0459(12) Uani 1 1 d . . . . .
O3 O 0.7356(2) 0.6027(4) 0.22714(16) 0.0654(11) Uani 1 1 d . . . . .
C3 C 0.5727(2) 0.5551(5) 0.3090(2) 0.0470(12) Uani 1 1 d . . . . .
H3 H 0.581286 0.462100 0.299256 0.056 Uiso 1 1 calc R . . . .
O4 O 0.6738(2) 1.0928(4) 0.37004(17) 0.0658(11) Uani 1 1 d . . . . .
C4 C 0.6038(2) 0.6740(5) 0.29520(18) 0.0407(11) Uani 1 1 d . . . . .
O5 O 0.72934(18) 0.8886(4) 0.37021(16) 0.0642(11) Uani 1 1 d . . . . .
C5 C 0.6667(2) 0.8321(5) 0.2589(2) 0.0449(12) Uani 1 1 d . . . . .
H5A H 0.651715 0.860705 0.219203 0.054 Uiso 1 1 calc R . . . .
H5B H 0.713788 0.845651 0.273611 0.054 Uiso 1 1 calc R . . . .
C6 C 0.6318(2) 0.9220(5) 0.2936(2) 0.0439(11) Uani 1 1 d . . . . .
C7 C 0.5907(2) 0.8100(5) 0.3105(2) 0.0409(11) Uani 1 1 d . . . . .
C8 C 0.5111(4) 0.3286(7) 0.3479(3) 0.086(2) Uani 1 1 d . . . . .
H8A H 0.496615 0.304908 0.307696 0.103 Uiso 1 1 calc R . . . .
H8B H 0.558105 0.314498 0.362591 0.103 Uiso 1 1 calc R . . . .
C9 C 0.4789(5) 0.2368(9) 0.3775(4) 0.107(3) Uani 1 1 d . . . . .
H9A H 0.491553 0.264412 0.416859 0.160 Uiso 1 1 calc GR . . . .
H9B H 0.491424 0.138538 0.374619 0.160 Uiso 1 1 calc GR . . . .
H9C H 0.432312 0.246212 0.360972 0.160 Uiso 1 1 calc GR . . . .
C10 C 0.7499(3) 0.5111(5) 0.3297(2) 0.0474(12) Uani 1 1 d . . . . .
C11 C 0.7388(3) 0.3923(7) 0.3583(3) 0.0663(16) Uani 1 1 d . . . . .
H11 H 0.703889 0.331011 0.341475 0.080 Uiso 1 1 calc R . . . .
C12 C 0.7799(4) 0.3655(8) 0.4117(3) 0.081(2) Uani 1 1 d . . . . .
H12 H 0.772501 0.284794 0.431054 0.098 Uiso 1 1 calc R . . . .
C13 C 0.8319(3) 0.4542(8) 0.4378(3) 0.0729(18) Uani 1 1 d . . . . .
C14 C 0.8419(3) 0.5734(7) 0.4085(3) 0.0736(18) Uani 1 1 d . . . . .
H14 H 0.876655 0.635122 0.425550 0.088 Uiso 1 1 calc R . . . .
C15 C 0.8009(3) 0.6029(6) 0.3540(3) 0.0627(15) Uani 1 1 d . . . . .
H15 H 0.808004 0.683349 0.334341 0.075 Uiso 1 1 calc R . . . .
C16 C 0.8786(4) 0.4234(10) 0.4974(3) 0.120(3) Uani 1 1 d . . . . .
H16A H 0.911457 0.355873 0.494924 0.180 Uiso 1 1 calc GR . . . .
H16B H 0.854483 0.383648 0.520498 0.180 Uiso 1 1 calc GR . . . .
H16C H 0.899341 0.511473 0.514148 0.180 Uiso 1 1 calc GR . . . .
C17 C 0.5920(3) 1.0452(6) 0.2590(2) 0.0542(13) Uani 1 1 d . . . . .
H17A H 0.562261 1.008031 0.224244 0.081 Uiso 1 1 calc GR . . . .
H17B H 0.620960 1.113653 0.250320 0.081 Uiso 1 1 calc GR . . . .
H17C H 0.567589 1.091709 0.280494 0.081 Uiso 1 1 calc GR . . . .
C18 C 0.6795(2) 0.9822(6) 0.3481(2) 0.0453(12) Uani 1 1 d . . . . .
C19 C 0.7804(3) 0.9278(6) 0.4193(2) 0.0575(14) Uani 1 1 d . . . . .
C20 C 0.7741(4) 0.9113(9) 0.4717(3) 0.089(2) Uani 1 1 d . . . . .
H20 H 0.734270 0.883202 0.475729 0.106 Uiso 1 1 calc R . . . .
C21 C 0.8280(4) 0.9373(11) 0.5191(3) 0.114(3) Uani 1 1 d . . . . .
H21 H 0.824126 0.927707 0.555289 0.137 Uiso 1 1 calc R . . . .
C22 C 0.8862(4) 0.9764(9) 0.5133(3) 0.093(2) Uani 1 1 d . . . . .
H22 H 0.922502 0.991023 0.545256 0.112 Uiso 1 1 calc R . . . .
C23 C 0.8913(3) 0.9939(8) 0.4606(3) 0.079(2) Uani 1 1 d . . . . .
H23 H 0.931024 1.021904 0.456473 0.095 Uiso 1 1 calc R . . . .
C24 C 0.8381(3) 0.9707(7) 0.4132(2) 0.0702(17) Uani 1 1 d . . . . .
H24 H 0.841632 0.984274 0.377076 0.084 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
Cl1 C1 1.729(5) . ?
S1 O2 1.425(4) . ?
S1 N2 1.635(4) . ?
S1 O3 1.428(4) . ?
S1 C10 1.763(5) . ?
O1 C2 1.342(6) . ?
O1 C8 1.478(7) . ?
N1 C1 1.321(6) . ?
N1 C7 1.338(6) . ?
C1 C2 1.414(7) . ?
N2 C4 1.410(6) . ?
N2 C5 1.485(6) . ?
C2 C3 1.391(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(7) . ?
O4 C18 1.186(6) . ?
C4 C7 1.371(7) . ?
O5 C18 1.355(6) . ?
O5 C19 1.406(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.551(7) . ?
C6 C7 1.506(6) . ?
C6 C17 1.522(7) . ?
C6 C18 1.520(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.436(9) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.369(8) . ?
C10 C15 1.370(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.362(9) . ?
C12 H12 0.9300 . ?
C12 C13 1.375(10) . ?
C13 C14 1.376(9) . ?
C13 C16 1.528(9) . ?
C14 H14 0.9300 . ?
C14 C15 1.388(8) . ?
C15 H15 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 . ?
C19 C20 1.354(9) . ?
C19 C24 1.356(8) . ?
C20 H20 0.9300 . ?
C20 C21 1.388(10) . ?
C21 H21 0.9300 . ?
C21 C22 1.354(10) . ?
C22 H22 0.9300 . ?
C22 C23 1.353(9) . ?
C23 H23 0.9300 . ?
C23 C24 1.374(8) . ?
C24 H24 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
O2 S1 N2 106.9(2) . . ?
O2 S1 O3 120.3(2) . . ?
O2 S1 C10 107.8(2) . . ?
N2 S1 C10 107.3(2) . . ?
O3 S1 N2 104.9(2) . . ?
O3 S1 C10 109.0(2) . . ?
C2 O1 C8 116.8(4) . . ?
C1 N1 C7 116.3(4) . . ?
N1 C1 Cl1 116.4(4) . . ?
N1 C1 C2 124.3(5) . . ?
C2 C1 Cl1 119.4(4) . . ?
C4 N2 S1 124.9(3) . . ?
C4 N2 C5 109.1(4) . . ?
C5 N2 S1 121.7(3) . . ?
O1 C2 C1 116.7(5) . . ?
O1 C2 C3 125.0(5) . . ?
C3 C2 C1 118.4(5) . . ?
C2 C3 H3 121.6 . . ?
C4 C3 C2 116.7(5) . . ?
C4 C3 H3 121.6 . . ?
C3 C4 N2 128.9(5) . . ?
C7 C4 N2 110.6(4) . . ?
C7 C4 C3 120.5(5) . . ?
C18 O5 C19 119.2(4) . . ?
N2 C5 H5A 110.5 . . ?
N2 C5 H5B 110.5 . . ?
N2 C5 C6 106.0(4) . . ?
H5A C5 H5B 108.7 . . ?
C6 C5 H5A 110.5 . . ?
C6 C5 H5B 110.5 . . ?
C7 C6 C5 102.2(4) . . ?
C7 C6 C17 113.5(4) . . ?
C7 C6 C18 107.3(4) . . ?
C17 C6 C5 112.0(4) . . ?
C18 C6 C5 112.5(4) . . ?
C18 C6 C17 109.1(4) . . ?
N1 C7 C4 123.8(4) . . ?
N1 C7 C6 124.5(4) . . ?
C4 C7 C6 111.7(4) . . ?
O1 C8 H8A 109.9 . . ?
O1 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
C9 C8 O1 108.8(6) . . ?
C9 C8 H8A 109.9 . . ?
C9 C8 H8B 109.9 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 S1 119.6(4) . . ?
C11 C10 C15 121.2(5) . . ?
C15 C10 S1 119.2(4) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 118.9(6) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 H12 119.0 . . ?
C11 C12 C13 122.0(6) . . ?
C13 C12 H12 119.0 . . ?
C12 C13 C14 118.2(6) . . ?
C12 C13 C16 122.2(7) . . ?
C14 C13 C16 119.6(7) . . ?
C13 C14 H14 119.5 . . ?
C13 C14 C15 120.9(6) . . ?
C15 C14 H14 119.5 . . ?
C10 C15 C14 118.7(6) . . ?
C10 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
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 . . ?
C6 C17 H17A 109.5 . . ?
C6 C17 H17B 109.5 . . ?
C6 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O4 C18 O5 123.6(5) . . ?
O4 C18 C6 125.9(5) . . ?
O5 C18 C6 110.4(4) . . ?
C20 C19 O5 120.8(6) . . ?
C20 C19 C24 120.8(6) . . ?
C24 C19 O5 118.1(5) . . ?
C19 C20 H20 120.6 . . ?
C19 C20 C21 118.8(7) . . ?
C21 C20 H20 120.6 . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.7(7) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 H22 120.3 . . ?
C23 C22 C21 119.5(6) . . ?
C23 C22 H22 120.3 . . ?
C22 C23 H23 119.7 . . ?
C22 C23 C24 120.6(7) . . ?
C24 C23 H23 119.7 . . ?
C19 C24 C23 119.6(6) . . ?
C19 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C1 C2 O1 -2.0(6) . . . . ?
Cl1 C1 C2 C3 178.9(4) . . . . ?
S1 N2 C4 C3 -25.4(7) . . . . ?
S1 N2 C4 C7 155.7(4) . . . . ?
S1 N2 C5 C6 -152.6(3) . . . . ?
S1 C10 C11 C12 179.5(5) . . . . ?
S1 C10 C15 C14 -179.8(5) . . . . ?
O1 C2 C3 C4 -178.5(4) . . . . ?
N1 C1 C2 O1 178.1(4) . . . . ?
N1 C1 C2 C3 -1.1(8) . . . . ?
C1 N1 C7 C4 1.0(7) . . . . ?
C1 N1 C7 C6 -177.8(4) . . . . ?
C1 C2 C3 C4 0.6(7) . . . . ?
O2 S1 N2 C4 52.6(4) . . . . ?
O2 S1 N2 C5 -153.2(4) . . . . ?
O2 S1 C10 C11 -10.4(5) . . . . ?
O2 S1 C10 C15 169.4(4) . . . . ?
N2 S1 C10 C11 104.4(5) . . . . ?
N2 S1 C10 C15 -75.7(5) . . . . ?
N2 C4 C7 N1 177.6(4) . . . . ?
N2 C4 C7 C6 -3.5(5) . . . . ?
N2 C5 C6 C7 -6.7(5) . . . . ?
N2 C5 C6 C17 -128.7(4) . . . . ?
N2 C5 C6 C18 108.0(4) . . . . ?
C2 O1 C8 C9 170.6(6) . . . . ?
C2 C3 C4 N2 -178.3(4) . . . . ?
C2 C3 C4 C7 0.6(7) . . . . ?
O3 S1 N2 C4 -178.7(4) . . . . ?
O3 S1 N2 C5 -24.5(4) . . . . ?
O3 S1 C10 C11 -142.6(4) . . . . ?
O3 S1 C10 C15 37.3(5) . . . . ?
C3 C4 C7 N1 -1.5(7) . . . . ?
C3 C4 C7 C6 177.5(4) . . . . ?
C4 N2 C5 C6 5.2(5) . . . . ?
O5 C19 C20 C21 173.4(7) . . . . ?
O5 C19 C24 C23 -172.6(6) . . . . ?
C5 N2 C4 C3 177.7(5) . . . . ?
C5 N2 C4 C7 -1.3(5) . . . . ?
C5 C6 C7 N1 -174.7(4) . . . . ?
C5 C6 C7 C4 6.4(5) . . . . ?
C5 C6 C18 O4 147.8(5) . . . . ?
C5 C6 C18 O5 -34.5(5) . . . . ?
C7 N1 C1 Cl1 -179.7(3) . . . . ?
C7 N1 C1 C2 0.3(7) . . . . ?
C7 C6 C18 O4 -100.5(6) . . . . ?
C7 C6 C18 O5 77.1(5) . . . . ?
C8 O1 C2 C1 -173.9(5) . . . . ?
C8 O1 C2 C3 5.2(7) . . . . ?
C10 S1 N2 C4 -62.9(4) . . . . ?
C10 S1 N2 C5 91.4(4) . . . . ?
C10 C11 C12 C13 0.1(10) . . . . ?
C11 C10 C15 C14 0.1(9) . . . . ?
C11 C12 C13 C14 0.2(11) . . . . ?
C11 C12 C13 C16 -179.2(7) . . . . ?
C12 C13 C14 C15 -0.5(10) . . . . ?
C13 C14 C15 C10 0.3(10) . . . . ?
C15 C10 C11 C12 -0.3(9) . . . . ?
C16 C13 C14 C15 179.0(6) . . . . ?
C17 C6 C7 N1 -53.8(6) . . . . ?
C17 C6 C7 C4 127.3(5) . . . . ?
C17 C6 C18 O4 22.9(7) . . . . ?
C17 C6 C18 O5 -159.5(4) . . . . ?
C18 O5 C19 C20 82.6(7) . . . . ?
C18 O5 C19 C24 -103.0(6) . . . . ?
C18 C6 C7 N1 66.8(6) . . . . ?
C18 C6 C7 C4 -112.1(4) . . . . ?
C19 O5 C18 O4 -5.3(8) . . . . ?
C19 O5 C18 C6 176.9(4) . . . . ?
C19 C20 C21 C22 -0.9(14) . . . . ?
C20 C19 C24 C23 1.8(11) . . . . ?
C20 C21 C22 C23 1.7(15) . . . . ?
C21 C22 C23 C24 -0.8(13) . . . . ?
C22 C23 C24 C19 -1.0(11) . . . . ?
C24 C19 C20 C21 -0.9(11) . . . . ?

_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 1.302
_oxdiff_exptl_absorpt_empirical_full_min 0.644
